# Electronic Supplementary Material (ESI) for Chemical Science. # This journal is © The Royal Society of Chemistry 2020 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_zhangy_0626 _database_code_depnum_ccdc_archive 'CCDC 1962272' loop_ _audit_author_name _audit_author_address 'YE ZHANG' ;LANZHOU UNIVERSITY China ; _audit_update_record ; 2019-10-29 deposited with the CCDC. 2020-03-11 downloaded from the CCDC. ; _audit_creation_date 2019-06-28 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _shelx_SHELXL_version_number 2018/3 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C22 H28 O5 S' _chemical_formula_sum 'C22 H28 O5 S' _chemical_formula_weight 404.50 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3975(3) _cell_length_b 10.7485(5) _cell_length_c 13.1441(5) _cell_angle_alpha 92.571(3) _cell_angle_beta 96.250(4) _cell_angle_gamma 97.449(4) _cell_volume 1028.29(8) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5801 _cell_measurement_temperature 292.1(3) _cell_measurement_theta_max 69.8890 _cell_measurement_theta_min 6.7770 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _exptl_absorpt_coefficient_mu 1.651 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.48684 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description plate _exptl_crystal_F_000 432 _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_unetI/netI 0.0304 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 14982 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 66.589 _diffrn_reflns_theta_max 66.589 _diffrn_reflns_theta_min 4.156 _diffrn_ambient_environment air _diffrn_ambient_temperature 292.1(3) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0733 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 44.00 116.00 1.00 1.50 -- 108.00-111.00 150.00 72 2 \w 41.00 95.00 1.00 1.50 -- 108.00 -63.00 150.00 54 3 \w 43.00 72.00 1.00 1.00 -- 64.00 42.00 130.49 29 4 \w 67.00 98.00 1.00 1.50 -- 84.00 46.00 157.56 31 5 \w 86.00 112.00 1.00 1.50 -- 108.00 63.00 150.00 26 6 \w 112.00 168.00 1.00 1.50 -- 108.00 77.00 120.00 56 7 \w 98.00 125.00 1.00 1.00 -- 60.00 76.00 40.65 27 8 \w 83.00 114.00 1.00 1.50 -- 104.00 60.00 -4.43 31 9 \w 113.00 169.00 1.00 1.50 -- 108.00 77.00 -30.00 56 10 \w 116.00 177.00 1.00 1.50 -- 108.00 77.00 -90.00 61 11 \w 102.00 151.00 1.00 1.50 -- 108.00 178.00 0.00 49 12 \w 79.00 176.00 1.00 1.50 -- 108.00 77.00 0.00 97 13 \w 84.00 130.00 1.00 1.00 -- 64.00 66.00-124.42 46 14 \w 87.00 112.00 1.00 1.50 -- 108.00 63.00-150.00 25 15 \w 78.00 168.00 1.00 1.50 -- 108.00 77.00-150.00 90 16 \w 83.00 110.00 1.00 1.50 -- 108.00 38.00 0.00 27 17 \w 78.00 160.00 1.00 1.50 -- 108.00 77.00 -60.00 82 18 \w 87.00 112.00 1.00 1.50 -- 108.00 63.00 60.00 25 19 \w 79.00 177.00 1.00 1.50 -- 108.00 77.00 30.00 98 20 \w 86.00 112.00 1.00 1.50 -- 108.00 63.00 -60.00 26 21 \w 78.00 104.00 1.00 1.50 -- 108.00 77.00 -30.00 26 22 \w 78.00 113.00 1.00 1.50 -- 108.00 77.00 -90.00 35 23 \w 79.00 160.00 1.00 1.50 -- 108.00 77.00-120.00 81 24 \w 81.00 177.00 1.00 1.50 -- 108.00 77.00-180.00 96 25 \w 59.00 92.00 1.00 1.50 -- 88.00 75.00-163.19 33 26 \w 54.00 103.00 1.00 1.00 -- 80.00 72.00 -92.70 49 27 \w 51.00 106.00 1.00 1.00 -- 72.00 55.00 -3.17 55 28 \w 71.00 100.00 1.00 1.50 -- 92.00 54.00 56.73 29 29 \w 78.00 154.00 1.00 1.50 -- 108.00 77.00 60.00 76 30 \w 78.00 176.00 1.00 1.50 -- 108.00 77.00 150.00 98 31 \w 79.00 107.00 1.00 1.50 -- 108.00 77.00 120.00 28 32 \w 80.00 166.00 1.00 1.50 -- 108.00 77.00 90.00 86 33 \w 67.00 93.00 1.00 1.50 -- 88.00 51.00 129.95 26 34 \w 48.00 75.00 1.00 1.00 -- 68.00 55.00 138.24 27 35 \w 49.00 140.00 1.00 1.00 -- 72.00 66.00 164.20 91 36 \w 41.00 68.00 1.00 1.00 -- 0.00 19.00 -30.00 27 37 \w 17.00 44.00 1.00 1.00 -- 48.00 78.00-115.08 27 38 \w 41.00 79.00 1.00 1.00 -- 64.00 66.00-124.42 38 39 \w 48.00 113.00 1.00 1.00 -- 76.00 77.00 -72.18 65 40 \w 47.00 133.00 1.00 1.00 -- 68.00 63.00 23.94 86 41 \w 43.00 130.00 1.00 1.00 -- 72.00 75.00-110.92 87 42 \w 45.00 70.00 1.00 1.00 -- 0.00 38.00-180.00 25 43 \w 24.00 50.00 1.00 1.00 -- 54.00 77.00-150.00 26 44 \w 37.00 62.00 1.00 1.00 -- 60.00 67.00-174.60 25 45 \w 28.00 74.00 1.00 1.00 -- 56.00 73.00-131.03 46 46 \w 20.00 45.00 1.00 1.00 -- 52.00 81.00 -38.20 25 47 \w 24.00 50.00 1.00 1.00 -- 54.00 77.00 0.00 26 48 \w 31.00 66.00 1.00 1.00 -- 60.00 76.00 40.65 35 49 \w 27.00 66.00 1.00 1.00 -- 54.00 77.00 60.00 39 50 \w 38.00 64.00 1.00 1.00 -- 60.00 62.00 118.01 26 51 \w 15.00 43.00 1.00 1.00 -- 48.00 82.00 153.27 28 52 \w 9.00 34.00 1.00 1.00 -- 44.00 85.00 96.32 25 53 \w 5.00 30.00 1.00 1.00 -- 40.00 85.00 65.41 25 54 \w 2.00 40.00 1.00 1.00 -- 0.00 19.00 -30.00 38 55 \w 43.00 138.00 1.00 1.50 -- 108.00 -77.00 -30.00 95 56 \w 53.00 89.00 1.00 1.50 -- 108.00-111.00-180.00 36 57 \w 28.00 87.00 1.00 1.00 -- 54.00-125.00 -90.00 59 58 \w 36.00 116.00 1.00 1.50 -- 108.00-111.00 -30.00 80 59 \w 6.00 85.00 1.00 1.00 -- 54.00 -99.00 60.00 79 60 \w -14.00 74.00 1.00 1.00 -- 54.00 -57.00 -90.00 88 61 \w -20.00 30.00 1.00 1.00 -- 0.00 38.00-180.00 50 62 \w 7.00 33.00 1.00 1.00 -- 44.00 89.00 -77.24 26 63 \w 25.00 51.00 1.00 1.00 -- 54.00 77.00 -60.00 26 64 \w -28.00 -3.00 1.00 1.00 -- 0.00 19.00 -30.00 25 65 \w -24.00 4.00 1.00 1.00 -- 24.00 111.00 68.59 28 66 \w -19.00 43.00 1.00 1.00 -- 0.00 -19.00 120.00 62 67 \w -8.00 72.00 1.00 1.00 -- 54.00 -57.00 120.00 80 68 \w -24.00 1.00 1.00 1.00 -- 28.00 117.00-130.18 25 69 \w -62.00 -33.00 1.00 1.00 -- 0.00 -19.00 120.00 29 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0698395000 _diffrn_orient_matrix_UB_12 0.1028010000 _diffrn_orient_matrix_UB_13 -0.0658448000 _diffrn_orient_matrix_UB_21 0.0336692000 _diffrn_orient_matrix_UB_22 -0.0739443000 _diffrn_orient_matrix_UB_23 -0.0977321000 _diffrn_orient_matrix_UB_31 -0.1967211000 _diffrn_orient_matrix_UB_32 -0.0702378000 _diffrn_orient_matrix_UB_33 -0.0080497000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 3088 _reflns_number_total 3632 _reflns_odcompleteness_completeness 99.86 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.304 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.043 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 254 _refine_ls_number_reflns 3632 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0428 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0634P)^2^+0.2953P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1155 _refine_ls_wR_factor_ref 0.1223 _refine_special_details ? _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C2(H2) 2.b Secondary CH2 refined with riding coordinates: C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C9(H9A,H9B), C10(H10A, H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B) 2.c Aromatic/amide H refined with riding coordinates: C17(H17), C18(H18), C20(H20), C21(H21) 2.d Idealised Me refined as rotating group: C22(H22A,H22B,H22C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary ? loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.26333(7) 0.33623(4) 0.91508(3) 0.04391(17) Uani 1 1 d . . . . . O1 O -0.1622(3) 0.87047(19) 0.61252(13) 0.0920(7) Uani 1 1 d . . . . . O2 O -0.0575(2) 0.63465(15) 0.44756(10) 0.0583(4) Uani 1 1 d . . . . . O3 O 0.3165(2) 0.48230(13) 0.92510(10) 0.0529(4) Uani 1 1 d . . . . . O4 O 0.0715(2) 0.30530(18) 0.88719(13) 0.0680(5) Uani 1 1 d . . . . . O5 O 0.3435(2) 0.29585(14) 1.00921(10) 0.0553(4) Uani 1 1 d . . . . . C1 C 0.1178(2) 0.76290(16) 0.81302(12) 0.0341(4) Uani 1 1 d . . . . . C2 C 0.0350(3) 0.86530(17) 0.87437(14) 0.0434(5) Uani 1 1 d . . . . . H2 H -0.045528 0.826365 0.921905 0.052 Uiso 1 1 calc R . . . . C3 C 0.1996(3) 0.9486(2) 0.93308(18) 0.0599(6) Uani 1 1 d . . . . . H3A H 0.218627 0.924414 1.003259 0.072 Uiso 1 1 calc R . . . . H3B H 0.179162 1.035929 0.934032 0.072 Uiso 1 1 calc R . . . . C4 C 0.3671(3) 0.9305(2) 0.87755(17) 0.0562(6) Uani 1 1 d . . . . . H4A H 0.457602 0.894671 0.922090 0.067 Uiso 1 1 calc R . . . . H4B H 0.423327 1.010190 0.856214 0.067 Uiso 1 1 calc R . . . . C5 C 0.2941(3) 0.84030(18) 0.78396(15) 0.0446(5) Uani 1 1 d . . . . . H5A H 0.383807 0.785629 0.769465 0.053 Uiso 1 1 calc R . . . . H5B H 0.266329 0.886853 0.723973 0.053 Uiso 1 1 calc R . . . . C6 C -0.0750(4) 0.9303(2) 0.79221(18) 0.0642(7) Uani 1 1 d . . . . . H6A H -0.193771 0.942004 0.813053 0.077 Uiso 1 1 calc R . . . . H6B H -0.009726 1.011890 0.781013 0.077 Uiso 1 1 calc R . . . . C7 C -0.0979(3) 0.8458(2) 0.69613(16) 0.0535(5) Uani 1 1 d . . . . . C8 C -0.0265(2) 0.72228(16) 0.71894(13) 0.0360(4) Uani 1 1 d . . . . . C9 C -0.1908(3) 0.6299(2) 0.74461(15) 0.0495(5) Uani 1 1 d . . . . . H9A H -0.147905 0.551996 0.764437 0.059 Uiso 1 1 calc R . . . . H9B H -0.241583 0.665412 0.802610 0.059 Uiso 1 1 calc R . . . . C10 C -0.3416(3) 0.6015(3) 0.65468(18) 0.0670(7) Uani 1 1 d . . . . . H10A H -0.395947 0.677262 0.640489 0.080 Uiso 1 1 calc R . . . . H10B H -0.437073 0.538722 0.673064 0.080 Uiso 1 1 calc R . . . . C11 C -0.2678(3) 0.5537(3) 0.55841(19) 0.0697(7) Uani 1 1 d . . . . . H11A H -0.250931 0.466421 0.565513 0.084 Uiso 1 1 calc R . . . . H11B H -0.359755 0.556515 0.500328 0.084 Uiso 1 1 calc R . . . . C12 C -0.0921(3) 0.62400(19) 0.53508(14) 0.0453(5) Uani 1 1 d . . . . . C13 C 0.0494(3) 0.66870(18) 0.62466(13) 0.0390(4) Uani 1 1 d . . . . . H13A H 0.138718 0.732962 0.602437 0.047 Uiso 1 1 calc R . . . . H13B H 0.113430 0.598870 0.644855 0.047 Uiso 1 1 calc R . . . . C14 C 0.1636(3) 0.65946(17) 0.88474(13) 0.0394(4) Uani 1 1 d . . . . . H14A H 0.243266 0.698689 0.944153 0.047 Uiso 1 1 calc R . . . . H14B H 0.050637 0.622051 0.908721 0.047 Uiso 1 1 calc R . . . . C15 C 0.2541(4) 0.5560(2) 0.84004(15) 0.0563(6) Uani 1 1 d . . . . . H15A H 0.167629 0.503124 0.790265 0.068 Uiso 1 1 calc R . . . . H15B H 0.357462 0.590857 0.806003 0.068 Uiso 1 1 calc R . . . . C16 C 0.3772(3) 0.28593(17) 0.81379(14) 0.0383(4) Uani 1 1 d . . . . . C17 C 0.2771(3) 0.2330(2) 0.72391(15) 0.0481(5) Uani 1 1 d . . . . . H17 H 0.149730 0.226612 0.715948 0.058 Uiso 1 1 calc R . . . . C18 C 0.3679(3) 0.1898(2) 0.64604(16) 0.0536(5) Uani 1 1 d . . . . . H18 H 0.300414 0.154108 0.585564 0.064 Uiso 1 1 calc R . . . . C19 C 0.5572(3) 0.19833(19) 0.65598(16) 0.0483(5) Uani 1 1 d . . . . . C20 C 0.6551(3) 0.2536(2) 0.74670(17) 0.0559(5) Uani 1 1 d . . . . . H20 H 0.782584 0.261154 0.754380 0.067 Uiso 1 1 calc R . . . . C21 C 0.5670(3) 0.2975(2) 0.82537(16) 0.0511(5) Uani 1 1 d . . . . . H21 H 0.634249 0.334452 0.885505 0.061 Uiso 1 1 calc R . . . . C22 C 0.6562(4) 0.1505(3) 0.5712(2) 0.0717(7) Uani 1 1 d . . . . . H22A H 0.673059 0.064624 0.580882 0.107 Uiso 1 1 calc GR . . . . H22B H 0.773649 0.200730 0.572276 0.107 Uiso 1 1 calc GR . . . . H22C H 0.584926 0.155781 0.506345 0.107 Uiso 1 1 calc GR . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0459(3) 0.0454(3) 0.0402(3) 0.00828(19) 0.0004(2) 0.0069(2) O1 0.1368(19) 0.0801(13) 0.0600(11) 0.0009(9) -0.0315(11) 0.0551(12) O2 0.0727(11) 0.0684(10) 0.0337(7) 0.0004(6) -0.0050(7) 0.0192(8) O3 0.0728(10) 0.0418(8) 0.0438(7) 0.0063(6) -0.0092(7) 0.0191(7) O4 0.0455(9) 0.0949(13) 0.0617(10) 0.0011(9) 0.0061(7) 0.0042(8) O5 0.0726(11) 0.0549(9) 0.0394(7) 0.0160(6) 0.0013(7) 0.0127(7) C1 0.0384(10) 0.0312(9) 0.0318(8) 0.0009(7) 0.0005(7) 0.0046(7) C2 0.0516(12) 0.0374(10) 0.0412(10) -0.0050(8) 0.0032(8) 0.0100(9) C3 0.0712(16) 0.0474(12) 0.0559(13) -0.0160(10) -0.0049(11) 0.0053(11) C4 0.0538(13) 0.0441(12) 0.0630(13) -0.0051(10) -0.0118(10) -0.0041(10) C5 0.0441(11) 0.0423(10) 0.0443(10) 0.0036(8) 0.0000(8) -0.0018(8) C6 0.0814(17) 0.0502(13) 0.0616(14) -0.0087(10) -0.0097(12) 0.0304(12) C7 0.0602(14) 0.0498(12) 0.0498(12) 0.0001(9) -0.0097(10) 0.0200(10) C8 0.0373(10) 0.0362(9) 0.0335(9) -0.0006(7) 0.0001(7) 0.0059(8) C9 0.0410(11) 0.0590(13) 0.0459(11) -0.0067(9) 0.0088(9) -0.0025(9) C10 0.0345(12) 0.0947(19) 0.0657(14) -0.0216(13) 0.0037(10) -0.0035(12) C11 0.0413(13) 0.099(2) 0.0589(14) -0.0296(13) -0.0036(10) -0.0084(12) C12 0.0481(12) 0.0488(11) 0.0389(10) -0.0066(8) -0.0034(8) 0.0157(9) C13 0.0369(10) 0.0457(10) 0.0328(9) -0.0012(7) 0.0010(7) 0.0029(8) C14 0.0495(11) 0.0372(10) 0.0318(9) 0.0041(7) 0.0012(8) 0.0090(8) C15 0.0844(17) 0.0516(12) 0.0400(10) 0.0139(9) 0.0068(10) 0.0326(11) C16 0.0400(11) 0.0350(9) 0.0391(9) 0.0091(7) -0.0022(8) 0.0049(8) C17 0.0400(11) 0.0555(12) 0.0462(11) 0.0039(9) -0.0074(8) 0.0071(9) C18 0.0581(14) 0.0566(13) 0.0424(11) -0.0011(9) -0.0090(9) 0.0076(10) C19 0.0569(13) 0.0409(10) 0.0484(11) 0.0092(8) 0.0063(9) 0.0089(9) C20 0.0378(12) 0.0666(14) 0.0616(13) 0.0049(11) 0.0015(10) 0.0037(10) C21 0.0448(12) 0.0582(13) 0.0450(11) 0.0009(9) -0.0081(9) -0.0006(9) C22 0.0811(19) 0.0687(16) 0.0688(16) 0.0000(12) 0.0213(13) 0.0145(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O3 1.5643(15) . ? S1 O4 1.4187(17) . ? S1 O5 1.4233(14) . ? S1 C16 1.7526(19) . ? O1 C7 1.204(3) . ? O2 C12 1.213(2) . ? O3 C15 1.467(2) . ? C1 C2 1.562(2) . ? C1 C5 1.547(3) . ? C1 C8 1.550(2) . ? C1 C14 1.537(2) . ? C2 H2 0.9800 . ? C2 C3 1.526(3) . ? C2 C6 1.530(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 C4 1.534(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C4 C5 1.535(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 C7 1.503(3) . ? C7 C8 1.521(3) . ? C8 C9 1.544(3) . ? C8 C13 1.534(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 C10 1.525(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C11 1.526(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 C12 1.485(3) . ? C12 C13 1.504(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 C15 1.500(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.381(3) . ? C16 C21 1.385(3) . ? C17 H17 0.9300 . ? C17 C18 1.379(3) . ? C18 H18 0.9300 . ? C18 C19 1.382(3) . ? C19 C20 1.392(3) . ? C19 C22 1.505(3) . ? C20 H20 0.9300 . ? C20 C21 1.378(3) . ? C21 H21 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 C16 104.68(9) . . ? O4 S1 O3 110.01(10) . . ? O4 S1 O5 118.99(10) . . ? O4 S1 C16 108.56(10) . . ? O5 S1 O3 103.76(8) . . ? O5 S1 C16 109.87(9) . . ? C15 O3 S1 118.53(13) . . ? C5 C1 C2 101.02(15) . . ? C5 C1 C8 112.67(14) . . ? C8 C1 C2 104.78(14) . . ? C14 C1 C2 108.99(14) . . ? C14 C1 C5 111.36(15) . . ? C14 C1 C8 116.55(15) . . ? C1 C2 H2 110.6 . . ? C3 C2 C1 105.41(16) . . ? C3 C2 H2 110.6 . . ? C3 C2 C6 114.92(19) . . ? C6 C2 C1 104.44(15) . . ? C6 C2 H2 110.6 . . ? C2 C3 H3A 110.3 . . ? C2 C3 H3B 110.3 . . ? C2 C3 C4 107.06(16) . . ? H3A C3 H3B 108.6 . . ? C4 C3 H3A 110.3 . . ? C4 C3 H3B 110.3 . . ? C3 C4 H4A 110.6 . . ? C3 C4 H4B 110.6 . . ? C3 C4 C5 105.77(17) . . ? H4A C4 H4B 108.7 . . ? C5 C4 H4A 110.6 . . ? C5 C4 H4B 110.6 . . ? C1 C5 H5A 110.6 . . ? C1 C5 H5B 110.6 . . ? C4 C5 C1 105.55(16) . . ? C4 C5 H5A 110.6 . . ? C4 C5 H5B 110.6 . . ? H5A C5 H5B 108.8 . . ? C2 C6 H6A 110.4 . . ? C2 C6 H6B 110.4 . . ? H6A C6 H6B 108.6 . . ? C7 C6 C2 106.43(16) . . ? C7 C6 H6A 110.4 . . ? C7 C6 H6B 110.4 . . ? O1 C7 C6 125.9(2) . . ? O1 C7 C8 123.96(19) . . ? C6 C7 C8 110.11(16) . . ? C7 C8 C1 101.52(14) . . ? C7 C8 C9 107.08(17) . . ? C7 C8 C13 110.37(15) . . ? C9 C8 C1 113.00(15) . . ? C13 C8 C1 115.16(15) . . ? C13 C8 C9 109.19(15) . . ? C8 C9 H9A 109.1 . . ? C8 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C10 C9 C8 112.59(18) . . ? C10 C9 H9A 109.1 . . ? C10 C9 H9B 109.1 . . ? C9 C10 H10A 109.3 . . ? C9 C10 H10B 109.3 . . ? C9 C10 C11 111.75(18) . . ? H10A C10 H10B 107.9 . . ? C11 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 . . ? C10 C11 H11A 108.4 . . ? C10 C11 H11B 108.4 . . ? H11A C11 H11B 107.5 . . ? C12 C11 C10 115.52(19) . . ? C12 C11 H11A 108.4 . . ? C12 C11 H11B 108.4 . . ? O2 C12 C11 121.44(19) . . ? O2 C12 C13 121.2(2) . . ? C11 C12 C13 116.98(17) . . ? C8 C13 H13A 108.5 . . ? C8 C13 H13B 108.5 . . ? C12 C13 C8 115.08(16) . . ? C12 C13 H13A 108.5 . . ? C12 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? C1 C14 H14A 108.2 . . ? C1 C14 H14B 108.2 . . ? H14A C14 H14B 107.3 . . ? C15 C14 C1 116.42(15) . . ? C15 C14 H14A 108.2 . . ? C15 C14 H14B 108.2 . . ? O3 C15 C14 107.22(15) . . ? O3 C15 H15A 110.3 . . ? O3 C15 H15B 110.3 . . ? C14 C15 H15A 110.3 . . ? C14 C15 H15B 110.3 . . ? H15A C15 H15B 108.5 . . ? C17 C16 S1 119.88(15) . . ? C17 C16 C21 120.52(18) . . ? C21 C16 S1 119.59(15) . . ? C16 C17 H17 120.3 . . ? C18 C17 C16 119.37(19) . . ? C18 C17 H17 120.3 . . ? C17 C18 H18 119.3 . . ? C17 C18 C19 121.41(19) . . ? C19 C18 H18 119.3 . . ? C18 C19 C20 118.2(2) . . ? C18 C19 C22 121.4(2) . . ? C20 C19 C22 120.5(2) . . ? C19 C20 H20 119.3 . . ? C21 C20 C19 121.3(2) . . ? C21 C20 H20 119.3 . . ? C16 C21 H21 120.4 . . ? C20 C21 C16 119.19(19) . . ? C20 C21 H21 120.4 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S1 O3 C15 C14 129.19(17) . . . . ? S1 C16 C17 C18 -177.76(15) . . . . ? S1 C16 C21 C20 177.72(16) . . . . ? O1 C7 C8 C1 153.2(3) . . . . ? O1 C7 C8 C9 -88.1(3) . . . . ? O1 C7 C8 C13 30.6(3) . . . . ? O2 C12 C13 C8 145.46(18) . . . . ? O3 S1 C16 C17 -114.09(16) . . . . ? O3 S1 C16 C21 67.10(17) . . . . ? O4 S1 O3 C15 -51.34(17) . . . . ? O4 S1 C16 C17 3.36(19) . . . . ? O4 S1 C16 C21 -175.45(16) . . . . ? O5 S1 O3 C15 -179.67(15) . . . . ? O5 S1 C16 C17 135.05(16) . . . . ? O5 S1 C16 C21 -43.77(18) . . . . ? C1 C2 C3 C4 21.5(2) . . . . ? C1 C2 C6 C7 15.5(3) . . . . ? C1 C8 C9 C10 173.83(17) . . . . ? C1 C8 C13 C12 177.39(15) . . . . ? C1 C14 C15 O3 169.42(17) . . . . ? C2 C1 C5 C4 37.89(18) . . . . ? C2 C1 C8 C7 35.27(18) . . . . ? C2 C1 C8 C9 -79.06(18) . . . . ? C2 C1 C8 C13 154.50(15) . . . . ? C2 C1 C14 C15 -176.90(18) . . . . ? C2 C3 C4 C5 2.4(2) . . . . ? C2 C6 C7 O1 -172.6(3) . . . . ? C2 C6 C7 C8 7.1(3) . . . . ? C3 C2 C6 C7 130.4(2) . . . . ? C3 C4 C5 C1 -25.6(2) . . . . ? C5 C1 C2 C3 -36.25(19) . . . . ? C5 C1 C2 C6 85.23(19) . . . . ? C5 C1 C8 C7 -73.66(18) . . . . ? C5 C1 C8 C9 172.00(16) . . . . ? C5 C1 C8 C13 45.6(2) . . . . ? C5 C1 C14 C15 -66.3(2) . . . . ? C6 C2 C3 C4 -92.9(2) . . . . ? C6 C7 C8 C1 -26.5(2) . . . . ? C6 C7 C8 C9 92.2(2) . . . . ? C6 C7 C8 C13 -149.1(2) . . . . ? C7 C8 C9 C10 62.9(2) . . . . ? C7 C8 C13 C12 -68.4(2) . . . . ? C8 C1 C2 C3 -153.48(16) . . . . ? C8 C1 C2 C6 -32.0(2) . . . . ? C8 C1 C5 C4 149.17(16) . . . . ? C8 C1 C14 C15 64.8(2) . . . . ? C8 C9 C10 C11 54.8(3) . . . . ? C9 C8 C13 C12 49.0(2) . . . . ? C9 C10 C11 C12 -44.6(3) . . . . ? C10 C11 C12 O2 -148.4(2) . . . . ? C10 C11 C12 C13 38.3(3) . . . . ? C11 C12 C13 C8 -41.2(3) . . . . ? C13 C8 C9 C10 -56.6(2) . . . . ? C14 C1 C2 C3 81.1(2) . . . . ? C14 C1 C2 C6 -157.42(18) . . . . ? C14 C1 C5 C4 -77.72(19) . . . . ? C14 C1 C8 C7 155.80(16) . . . . ? C14 C1 C8 C9 41.5(2) . . . . ? C14 C1 C8 C13 -85.0(2) . . . . ? C16 S1 O3 C15 65.12(16) . . . . ? C16 C17 C18 C19 -0.1(3) . . . . ? C17 C16 C21 C20 -1.1(3) . . . . ? C17 C18 C19 C20 -0.9(3) . . . . ? C17 C18 C19 C22 179.7(2) . . . . ? C18 C19 C20 C21 0.8(3) . . . . ? C19 C20 C21 C16 0.2(3) . . . . ? C21 C16 C17 C18 1.0(3) . . . . ? C22 C19 C20 C21 -179.7(2) . . . . ? _shelx_res_file ; TITL zhangy_0626 in P-1 #2 zhangy_0626.res created by SHELXL-2018/3 at 08:57:49 on 28-Jun-2019 REM reset to P-1 #2 CELL 1.54184 7.397521 10.748507 13.144077 92.5705 96.25 97.4493 ZERR 2 0.000334 0.000451 0.000545 0.0034 0.0036 0.0036 LATT 1 SFAC C H O S UNIT 44 56 10 2 L.S. 4 0 0 PLAN 20 BOND $H HTAB conf fmap 2 53 ACTA SHEL 999 0.84 REM REM REM WGHT 0.063400 0.295300 FVAR 9.01569 S1 4 0.263331 0.336231 0.915079 11.00000 0.04589 0.04537 = 0.04016 0.00828 0.00037 0.00694 O1 3 -0.162168 0.870472 0.612518 11.00000 0.13677 0.08012 = 0.05998 0.00086 -0.03150 0.05506 O2 3 -0.057468 0.634651 0.447560 11.00000 0.07269 0.06841 = 0.03368 0.00044 -0.00495 0.01918 O3 3 0.316548 0.482296 0.925104 11.00000 0.07285 0.04178 = 0.04375 0.00631 -0.00918 0.01909 O4 3 0.071475 0.305304 0.887192 11.00000 0.04548 0.09495 = 0.06175 0.00109 0.00614 0.00418 O5 3 0.343456 0.295851 1.009212 11.00000 0.07261 0.05493 = 0.03935 0.01605 0.00125 0.01274 C1 1 0.117810 0.762896 0.813022 11.00000 0.03845 0.03119 = 0.03179 0.00091 0.00047 0.00464 C2 1 0.035013 0.865303 0.874369 11.00000 0.05165 0.03743 = 0.04115 -0.00501 0.00322 0.00996 AFIX 13 H2 2 -0.045528 0.826365 0.921905 11.00000 -1.20000 AFIX 0 C3 1 0.199556 0.948560 0.933076 11.00000 0.07121 0.04741 = 0.05590 -0.01601 -0.00492 0.00528 AFIX 23 H3A 2 0.218627 0.924414 1.003259 11.00000 -1.20000 H3B 2 0.179162 1.035929 0.934032 11.00000 -1.20000 AFIX 0 C4 1 0.367056 0.930456 0.877553 11.00000 0.05380 0.04409 = 0.06303 -0.00505 -0.01182 -0.00409 AFIX 23 H4A 2 0.457602 0.894671 0.922090 11.00000 -1.20000 H4B 2 0.423327 1.010190 0.856214 11.00000 -1.20000 AFIX 0 C5 1 0.294074 0.840302 0.783958 11.00000 0.04411 0.04228 = 0.04427 0.00357 -0.00002 -0.00175 AFIX 23 H5A 2 0.383807 0.785629 0.769465 11.00000 -1.20000 H5B 2 0.266329 0.886853 0.723973 11.00000 -1.20000 AFIX 0 C6 1 -0.074991 0.930311 0.792209 11.00000 0.08139 0.05018 = 0.06165 -0.00874 -0.00973 0.03039 AFIX 23 H6A 2 -0.193771 0.942004 0.813053 11.00000 -1.20000 H6B 2 -0.009726 1.011890 0.781013 11.00000 -1.20000 AFIX 0 C7 1 -0.097930 0.845782 0.696132 11.00000 0.06021 0.04983 = 0.04980 0.00012 -0.00969 0.01998 C8 1 -0.026548 0.722280 0.718943 11.00000 0.03731 0.03620 = 0.03349 -0.00063 0.00009 0.00587 C9 1 -0.190840 0.629923 0.744612 11.00000 0.04102 0.05898 = 0.04587 -0.00666 0.00881 -0.00246 AFIX 23 H9A 2 -0.147905 0.551996 0.764437 11.00000 -1.20000 H9B 2 -0.241583 0.665412 0.802610 11.00000 -1.20000 AFIX 0 C10 1 -0.341629 0.601532 0.654676 11.00000 0.03447 0.09467 = 0.06574 -0.02160 0.00365 -0.00345 AFIX 23 H10A 2 -0.395947 0.677262 0.640489 11.00000 -1.20000 H10B 2 -0.437073 0.538722 0.673064 11.00000 -1.20000 AFIX 0 C11 1 -0.267763 0.553748 0.558406 11.00000 0.04128 0.09884 = 0.05886 -0.02955 -0.00363 -0.00842 AFIX 23 H11A 2 -0.250931 0.466421 0.565513 11.00000 -1.20000 H11B 2 -0.359755 0.556515 0.500328 11.00000 -1.20000 AFIX 0 C12 1 -0.092081 0.624000 0.535083 11.00000 0.04809 0.04879 = 0.03886 -0.00663 -0.00337 0.01573 C13 1 0.049388 0.668698 0.624660 11.00000 0.03694 0.04573 = 0.03276 -0.00115 0.00102 0.00288 AFIX 23 H13A 2 0.138718 0.732962 0.602437 11.00000 -1.20000 H13B 2 0.113430 0.598870 0.644855 11.00000 -1.20000 AFIX 0 C14 1 0.163596 0.659457 0.884736 11.00000 0.04949 0.03722 = 0.03181 0.00413 0.00121 0.00903 AFIX 23 H14A 2 0.243266 0.698689 0.944153 11.00000 -1.20000 H14B 2 0.050637 0.622051 0.908721 11.00000 -1.20000 AFIX 0 C15 1 0.254080 0.555956 0.840039 11.00000 0.08438 0.05161 = 0.04002 0.01391 0.00675 0.03262 AFIX 23 H15A 2 0.167629 0.503124 0.790265 11.00000 -1.20000 H15B 2 0.357462 0.590857 0.806003 11.00000 -1.20000 AFIX 0 C16 1 0.377175 0.285928 0.813793 11.00000 0.03999 0.03503 = 0.03909 0.00913 -0.00217 0.00487 C17 1 0.277127 0.233024 0.723908 11.00000 0.04000 0.05549 = 0.04620 0.00387 -0.00743 0.00709 AFIX 43 H17 2 0.149730 0.226612 0.715948 11.00000 -1.20000 AFIX 0 C18 1 0.367943 0.189778 0.646038 11.00000 0.05807 0.05663 = 0.04237 -0.00111 -0.00896 0.00757 AFIX 43 H18 2 0.300414 0.154108 0.585564 11.00000 -1.20000 AFIX 0 C19 1 0.557163 0.198328 0.655976 11.00000 0.05691 0.04088 = 0.04836 0.00924 0.00634 0.00895 C20 1 0.655099 0.253644 0.746696 11.00000 0.03781 0.06664 = 0.06158 0.00488 0.00148 0.00373 AFIX 43 H20 2 0.782584 0.261154 0.754380 11.00000 -1.20000 AFIX 0 C21 1 0.567010 0.297513 0.825367 11.00000 0.04478 0.05822 = 0.04500 0.00094 -0.00806 -0.00058 AFIX 43 H21 2 0.634249 0.334452 0.885505 11.00000 -1.20000 AFIX 0 C22 1 0.656166 0.150537 0.571191 11.00000 0.08106 0.06869 = 0.06881 0.00000 0.02126 0.01453 AFIX 137 H22A 2 0.673059 0.064624 0.580882 11.00000 -1.50000 H22B 2 0.773649 0.200730 0.572276 11.00000 -1.50000 H22C 2 0.584926 0.155781 0.506345 11.00000 -1.50000 AFIX 0 HKLF 4 REM zhangy_0626 in P-1 #2 REM wR2 = 0.1223, GooF = S = 1.047, Restrained GooF = 1.047 for all data REM R1 = 0.0428 for 3088 Fo > 4sig(Fo) and 0.0507 for all 3632 data REM 254 parameters refined using 0 restraints END WGHT 0.0634 0.2952 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.304, deepest hole -0.367, 1-sigma level 0.043 Q1 1 0.3215 0.3139 0.8596 11.00000 0.05 0.30 Q2 1 0.0718 0.8081 0.8440 11.00000 0.05 0.25 Q3 1 0.0191 0.6975 0.6774 11.00000 0.05 0.22 Q4 1 -0.1270 1.0027 0.7967 11.00000 0.05 0.22 Q5 1 0.3641 0.8179 0.7252 11.00000 0.05 0.19 Q6 1 0.1995 0.7972 0.7968 11.00000 0.05 0.18 Q7 1 0.1376 0.7146 0.8437 11.00000 0.05 0.17 Q8 1 -0.4705 0.6021 0.6545 11.00000 0.05 0.17 Q9 1 0.0151 0.2648 0.8864 11.00000 0.05 0.16 Q10 1 0.0472 0.7414 0.7662 11.00000 0.05 0.16 Q11 1 0.2176 0.4265 0.9338 11.00000 0.05 0.15 Q12 1 -0.0593 0.7776 0.7037 11.00000 0.05 0.15 Q13 1 0.0363 0.3615 0.8406 11.00000 0.05 0.15 Q14 1 0.1067 0.4702 0.8196 11.00000 0.05 0.15 Q15 1 -0.1613 0.5774 0.5544 11.00000 0.05 0.14 Q16 1 0.3172 0.1750 0.6936 11.00000 0.05 0.14 Q17 1 0.2764 0.5351 0.7774 11.00000 0.05 0.14 Q18 1 -0.3115 0.5985 0.5957 11.00000 0.05 0.14 Q19 1 0.3416 0.2342 0.9663 11.00000 0.05 0.13 Q20 1 0.3887 0.2552 0.9693 11.00000 0.05 0.13 ; _shelx_res_checksum 11369 _olex2_date_sample_data_collection 2019-06-27 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.618 _oxdiff_exptl_absorpt_empirical_full_min 0.443 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_zhangye_1015 _database_code_depnum_ccdc_archive 'CCDC 1962275' loop_ _audit_author_name _audit_author_address 'YE ZHANG' ;LANZHOU UNIVERSITY China ; _audit_update_record ; 2019-10-29 deposited with the CCDC. 2020-03-11 downloaded from the CCDC. ; _audit_creation_date 2019-10-18 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _shelx_SHELXL_version_number 2018/3 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety '2(C15 H22 O3)' _chemical_formula_sum 'C30 H44 O6' _chemical_formula_weight 500.65 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.6688(3) _cell_length_b 22.4305(6) _cell_length_c 15.4747(5) _cell_angle_alpha 90 _cell_angle_beta 101.329(4) _cell_angle_gamma 90 _cell_volume 2610.00(14) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5177 _cell_measurement_temperature 292.89(12) _cell_measurement_theta_max 69.4980 _cell_measurement_theta_min 6.1850 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _exptl_absorpt_coefficient_mu 0.697 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.72852 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_F_000 1088 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_unetI/netI 0.0356 _diffrn_reflns_Laue_measured_fraction_full 0.959 _diffrn_reflns_Laue_measured_fraction_max 0.959 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 12604 _diffrn_reflns_point_group_measured_fraction_full 0.959 _diffrn_reflns_point_group_measured_fraction_max 0.959 _diffrn_reflns_theta_full 66.595 _diffrn_reflns_theta_max 66.595 _diffrn_reflns_theta_min 3.517 _diffrn_ambient_temperature 292.89(12) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.959 _diffrn_measured_fraction_theta_max 0.959 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -60.00 -15.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 125.0000 -120.0000 45 #__ type_ start__ end____ width___ exp.time_ 2 omega -69.00 -44.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 178.0000 120.0000 25 #__ type_ start__ end____ width___ exp.time_ 3 omega -86.00 -40.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 178.0000 -60.0000 46 #__ type_ start__ end____ width___ exp.time_ 4 omega -7.00 40.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -57.0000 60.0000 47 #__ type_ start__ end____ width___ exp.time_ 5 omega 23.00 91.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 77.0000 -30.0000 68 #__ type_ start__ end____ width___ exp.time_ 6 omega -14.00 77.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -77.0000 90.0000 91 #__ type_ start__ end____ width___ exp.time_ 7 omega 36.00 63.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -12.0000 -30.0000 27 #__ type_ start__ end____ width___ exp.time_ 8 omega 39.00 93.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -50.0000 120.0000 54 #__ type_ start__ end____ width___ exp.time_ 9 omega 35.00 69.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 120.0000 34 #__ type_ start__ end____ width___ exp.time_ 10 omega 37.00 99.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -50.0000 30.0000 62 #__ type_ start__ end____ width___ exp.time_ 11 omega 76.00 102.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -91.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 12 omega 102.00 176.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 50.0000 0.0000 74 #__ type_ start__ end____ width___ exp.time_ 13 omega 76.00 178.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -12.0000 -30.0000 102 #__ type_ start__ end____ width___ exp.time_ 14 omega 47.00 79.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -38.0000 -120.0000 32 #__ type_ start__ end____ width___ exp.time_ 15 omega 69.00 97.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 25.0000 60.0000 28 #__ type_ start__ end____ width___ exp.time_ 16 omega 35.00 61.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -91.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 17 omega 59.00 93.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -38.0000 60.0000 34 #__ type_ start__ end____ width___ exp.time_ 18 omega 45.00 126.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -63.0000 -60.0000 81 #__ type_ start__ end____ width___ exp.time_ 19 omega -49.00 -23.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 111.0000 60.0000 26 #__ type_ start__ end____ width___ exp.time_ 20 omega 30.00 56.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 57.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 21 omega -16.00 27.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -38.0000 -180.0000 43 #__ type_ start__ end____ width___ exp.time_ 22 omega 51.00 81.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -38.0000 -90.0000 30 #__ type_ start__ end____ width___ exp.time_ 23 omega 150.00 176.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 111.0000 -60.0000 26 #__ type_ start__ end____ width___ exp.time_ 24 omega 53.00 79.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -38.0000 -30.0000 26 #__ type_ start__ end____ width___ exp.time_ 25 omega 45.00 71.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 26 omega 110.00 136.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 111.0000 -60.0000 26 #__ type_ start__ end____ width___ exp.time_ 27 omega 90.00 115.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 -120.0000 25 #__ type_ start__ end____ width___ exp.time_ 28 omega 59.00 113.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 120.0000 54 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.1221208000 _diffrn_orient_matrix_UB_12 -0.0452613000 _diffrn_orient_matrix_UB_13 0.0337416000 _diffrn_orient_matrix_UB_21 0.1404157000 _diffrn_orient_matrix_UB_22 -0.0082940000 _diffrn_orient_matrix_UB_23 0.0851597000 _diffrn_orient_matrix_UB_31 -0.0855389000 _diffrn_orient_matrix_UB_32 0.0509989000 _diffrn_orient_matrix_UB_33 0.0438501000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_source 'SuperNova (Cu) X-ray Source' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 3722 _reflns_number_total 4422 _reflns_odcompleteness_completeness 95.86 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.279 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.040 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 327 _refine_ls_number_reflns 4422 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0456 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0703P)^2^+0.4835P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1221 _refine_ls_wR_factor_ref 0.1371 _refine_special_details ? _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All O(H) groups 2.a Ternary CH refined with riding coordinates: C22(H22), C20(H20) 2.b Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C9(H9A,H9B), C15(H15A,H15B), C19(H19A,H19B), C21(H21A,H21B), C23(H23A,H23B), C24(H24A,H24B), C26(H26A,H26B), C30(H30A,H30B), C32(H32A,H32B), C11(H11A,H11B), C14(H14A,H14B), C25(H25A,H25B), C27(H27A,H27B), C28(H28A, H28B), C31(H31A,H31B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B) 2.c Idealised tetrahedral OH refined as rotating group: O3(H3), O6(H6) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary ? loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.04753(17) 0.03278(6) 0.60409(8) 0.0459(3) Uani 1 1 d . . . . . O2 O 0.5369(2) -0.05159(7) 0.87537(9) 0.0593(4) Uani 1 1 d . . . . . O3 O 0.1006(2) -0.06466(6) 0.56750(8) 0.0583(4) Uani 1 1 d . . . . . H3 H 0.056875 -0.054452 0.517014 0.087 Uiso 1 1 calc GR . . . . C7 C 0.3962(2) -0.02565(7) 0.85918(11) 0.0415(4) Uani 1 1 d . . . . . C8 C 0.4781(2) 0.03800(8) 0.73745(12) 0.0456(4) Uani 1 1 d . . . . . H8A H 0.527818 0.071247 0.774264 0.055 Uiso 1 1 calc R . . . . H8B H 0.571101 0.008429 0.739567 0.055 Uiso 1 1 calc R . . . . C9 C 0.4207(3) 0.05988(8) 0.64256(13) 0.0493(4) Uani 1 1 d . . . . . H9A H 0.338114 0.092808 0.640972 0.059 Uiso 1 1 calc R . . . . H9B H 0.523896 0.074322 0.621361 0.059 Uiso 1 1 calc R . . . . C10 C 0.3258(2) 0.01060(7) 0.77558(10) 0.0352(3) Uani 1 1 d . . . . . C13 C 0.1985(2) 0.05438(7) 0.81048(11) 0.0363(4) Uani 1 1 d . . . . . C15 C 0.2292(2) -0.03655(7) 0.71066(10) 0.0373(4) Uani 1 1 d . . . . . H15A H 0.306477 -0.070890 0.711616 0.045 Uiso 1 1 calc R . . . . H15B H 0.123524 -0.049578 0.730936 0.045 Uiso 1 1 calc R . . . . C18 C 0.1750(3) -0.01474(7) 0.61598(11) 0.0412(4) Uani 1 1 d . . . . . C19 C 0.0526(3) 0.08439(8) 0.74263(12) 0.0466(4) Uani 1 1 d . . . . . H19A H -0.030664 0.102970 0.774086 0.056 Uiso 1 1 calc R . . . . H19B H 0.107142 0.116015 0.714376 0.056 Uiso 1 1 calc R . . . . C21 C 0.2622(3) -0.02571(8) 0.91829(12) 0.0503(5) Uani 1 1 d . . . . . H21A H 0.317604 -0.013353 0.977391 0.060 Uiso 1 1 calc R . . . . H21B H 0.213043 -0.065325 0.921286 0.060 Uiso 1 1 calc R . . . . C22 C 0.1166(2) 0.01804(7) 0.87839(11) 0.0413(4) Uani 1 1 d . . . . . H22 H 0.009532 -0.003212 0.849092 0.050 Uiso 1 1 calc R . . . . C23 C -0.0518(2) 0.04528(10) 0.67133(13) 0.0522(5) Uani 1 1 d . . . . . H23A H -0.081435 0.008130 0.697130 0.063 Uiso 1 1 calc R . . . . H23B H -0.162053 0.065076 0.645251 0.063 Uiso 1 1 calc R . . . . C24 C 0.3324(3) 0.01016(8) 0.58240(12) 0.0484(4) Uani 1 1 d . . . . . H24A H 0.292982 0.025557 0.523209 0.058 Uiso 1 1 calc R . . . . H24B H 0.417799 -0.021386 0.579993 0.058 Uiso 1 1 calc R . . . . C26 C 0.3040(3) 0.10223(7) 0.87111(13) 0.0493(4) Uani 1 1 d . . . . . H26A H 0.416412 0.086208 0.902203 0.059 Uiso 1 1 calc R . . . . H26B H 0.327542 0.136549 0.837025 0.059 Uiso 1 1 calc R . . . . C30 C 0.1860(4) 0.11960(9) 0.93593(15) 0.0622(6) Uani 1 1 d . . . . . H30A H 0.112043 0.153546 0.914018 0.075 Uiso 1 1 calc R . . . . H30B H 0.257901 0.129797 0.992829 0.075 Uiso 1 1 calc R . . . . C32 C 0.0708(3) 0.06459(9) 0.94365(14) 0.0571(5) Uani 1 1 d . . . . . H32A H -0.054439 0.074855 0.928865 0.069 Uiso 1 1 calc R . . . . H32B H 0.096833 0.049025 1.003284 0.069 Uiso 1 1 calc R . . . . O4 O 0.41418(19) 0.14656(6) 0.31948(11) 0.0588(4) Uani 1 1 d . . . . . O5 O -0.21544(19) 0.25459(7) 0.30998(11) 0.0661(4) Uani 1 1 d . . . . . O6 O 0.2053(2) 0.09146(6) 0.22396(11) 0.0629(4) Uani 1 1 d . . . . . H6 H 0.282930 0.080697 0.197732 0.094 Uiso 1 1 calc GR . . . . C11 C 0.0910(2) 0.16507(7) 0.30249(11) 0.0401(4) Uani 1 1 d . . . . . H11A H 0.084068 0.136396 0.348611 0.048 Uiso 1 1 calc R . . . . H11B H -0.017252 0.161533 0.258264 0.048 Uiso 1 1 calc R . . . . C12 C -0.0889(2) 0.23622(7) 0.36173(13) 0.0444(4) Uani 1 1 d . . . . . C14 C 0.2232(3) 0.29700(7) 0.47324(13) 0.0483(4) Uani 1 1 d . . . . . H14A H 0.332631 0.316049 0.465416 0.058 Uiso 1 1 calc R . . . . H14B H 0.123611 0.320310 0.442469 0.058 Uiso 1 1 calc R . . . . C16 C 0.2134(2) 0.23228(7) 0.43667(12) 0.0383(4) Uani 1 1 d . . . . . C17 C 0.0991(2) 0.22862(7) 0.34258(11) 0.0385(4) Uani 1 1 d . . . . . C20 C 0.0999(3) 0.20157(7) 0.49691(12) 0.0443(4) Uani 1 1 d . . . . . H20 H 0.119719 0.158390 0.498787 0.053 Uiso 1 1 calc R . . . . C25 C 0.4014(2) 0.20602(8) 0.44980(14) 0.0508(5) Uani 1 1 d . . . . . H25A H 0.474754 0.233360 0.423956 0.061 Uiso 1 1 calc R . . . . H25B H 0.449596 0.204560 0.512592 0.061 Uiso 1 1 calc R . . . . C27 C 0.4202(3) 0.14442(8) 0.41194(15) 0.0554(5) Uani 1 1 d . . . . . H27A H 0.532319 0.127034 0.440964 0.067 Uiso 1 1 calc R . . . . H27B H 0.325124 0.119034 0.423630 0.067 Uiso 1 1 calc R . . . . C28 C 0.1358(3) 0.27356(8) 0.27377(13) 0.0519(5) Uani 1 1 d . . . . . H28A H 0.029438 0.277540 0.228425 0.062 Uiso 1 1 calc R . . . . H28B H 0.160021 0.312135 0.301908 0.062 Uiso 1 1 calc R . . . . C29 C 0.2477(3) 0.14891(8) 0.26057(14) 0.0488(4) Uani 1 1 d . . . . . C31 C -0.0916(3) 0.21605(9) 0.45408(14) 0.0535(5) Uani 1 1 d . . . . . H31A H -0.166140 0.181022 0.453203 0.064 Uiso 1 1 calc R . . . . H31B H -0.137884 0.247356 0.486512 0.064 Uiso 1 1 calc R . . . . C33 C 0.2711(4) 0.19407(10) 0.19081(16) 0.0667(6) Uani 1 1 d . . . . . H33A H 0.168779 0.192759 0.142720 0.080 Uiso 1 1 calc R . . . . H33B H 0.375843 0.184122 0.167394 0.080 Uiso 1 1 calc R . . . . C34 C 0.2910(3) 0.25694(9) 0.23003(16) 0.0654(6) Uani 1 1 d . . . . . H34A H 0.400998 0.259281 0.273295 0.079 Uiso 1 1 calc R . . . . H34B H 0.298058 0.285412 0.183668 0.079 Uiso 1 1 calc R . . . . C35 C 0.2173(4) 0.29262(10) 0.57095(16) 0.0733(7) Uani 1 1 d . . . . . H35A H 0.132274 0.320954 0.585861 0.088 Uiso 1 1 calc R . . . . H35B H 0.333350 0.301357 0.606486 0.088 Uiso 1 1 calc R . . . . C36 C 0.1617(3) 0.22913(9) 0.58824(14) 0.0620(6) Uani 1 1 d . . . . . H36A H 0.065838 0.229315 0.620851 0.074 Uiso 1 1 calc R . . . . H36B H 0.261210 0.206997 0.621625 0.074 Uiso 1 1 calc R . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0445(7) 0.0499(7) 0.0405(6) 0.0051(5) 0.0017(5) 0.0047(5) O2 0.0576(9) 0.0688(9) 0.0477(7) 0.0012(6) 0.0008(6) 0.0273(7) O3 0.0882(11) 0.0418(7) 0.0387(6) -0.0018(5) -0.0027(7) -0.0120(7) C7 0.0460(10) 0.0357(8) 0.0398(8) -0.0043(6) 0.0010(7) 0.0058(7) C8 0.0324(9) 0.0449(9) 0.0589(10) 0.0002(8) 0.0074(8) -0.0017(7) C9 0.0415(10) 0.0442(9) 0.0656(11) 0.0112(8) 0.0185(9) -0.0020(7) C10 0.0328(8) 0.0295(7) 0.0414(8) -0.0001(6) 0.0030(7) 0.0002(6) C13 0.0367(8) 0.0275(7) 0.0442(8) -0.0018(6) 0.0066(7) -0.0004(6) C15 0.0442(9) 0.0292(7) 0.0374(8) 0.0005(6) 0.0055(7) -0.0009(6) C18 0.0498(10) 0.0330(8) 0.0383(8) 0.0009(6) 0.0024(7) 0.0001(7) C19 0.0457(10) 0.0413(9) 0.0537(10) 0.0042(7) 0.0118(8) 0.0127(7) C21 0.0618(12) 0.0443(9) 0.0463(9) 0.0062(7) 0.0139(9) 0.0077(8) C22 0.0433(9) 0.0355(8) 0.0460(9) -0.0024(7) 0.0112(8) -0.0025(7) C23 0.0339(9) 0.0671(12) 0.0535(10) 0.0076(9) 0.0037(8) 0.0080(8) C24 0.0542(11) 0.0472(9) 0.0460(9) 0.0085(7) 0.0153(8) 0.0085(8) C26 0.0566(11) 0.0330(8) 0.0584(11) -0.0092(7) 0.0115(9) -0.0079(8) C30 0.0843(16) 0.0420(10) 0.0636(12) -0.0146(9) 0.0227(12) 0.0000(10) C32 0.0690(14) 0.0496(10) 0.0586(11) -0.0048(9) 0.0268(10) 0.0034(10) O4 0.0418(7) 0.0528(7) 0.0861(10) -0.0091(7) 0.0231(7) 0.0023(6) O5 0.0406(8) 0.0693(9) 0.0800(10) -0.0059(8) -0.0089(7) 0.0143(7) O6 0.0687(10) 0.0439(7) 0.0835(10) -0.0226(7) 0.0331(8) -0.0090(7) C11 0.0359(9) 0.0337(8) 0.0501(9) -0.0042(7) 0.0068(7) -0.0033(6) C12 0.0329(9) 0.0325(8) 0.0633(11) -0.0086(7) -0.0017(8) 0.0025(6) C14 0.0450(10) 0.0310(8) 0.0661(11) -0.0065(7) 0.0043(9) -0.0021(7) C16 0.0323(8) 0.0282(7) 0.0525(9) -0.0022(6) 0.0032(7) -0.0008(6) C17 0.0325(8) 0.0296(7) 0.0514(9) -0.0020(6) 0.0032(7) 0.0002(6) C20 0.0461(10) 0.0344(8) 0.0527(10) -0.0004(7) 0.0107(8) -0.0006(7) C25 0.0318(9) 0.0433(9) 0.0720(12) -0.0045(8) -0.0025(9) 0.0008(7) C27 0.0371(10) 0.0439(10) 0.0816(14) -0.0015(9) 0.0025(9) 0.0102(8) C28 0.0600(12) 0.0362(8) 0.0579(11) 0.0053(8) 0.0079(9) 0.0010(8) C29 0.0484(11) 0.0365(8) 0.0654(11) -0.0090(8) 0.0206(9) -0.0045(7) C31 0.0412(10) 0.0487(10) 0.0738(13) -0.0033(9) 0.0189(9) -0.0025(8) C33 0.0819(16) 0.0570(12) 0.0714(13) -0.0025(10) 0.0400(13) -0.0057(11) C34 0.0787(16) 0.0470(10) 0.0777(14) 0.0086(10) 0.0326(13) -0.0097(10) C35 0.098(2) 0.0548(12) 0.0667(14) -0.0190(10) 0.0149(13) -0.0124(12) C36 0.0759(15) 0.0555(11) 0.0538(11) -0.0050(9) 0.0103(11) -0.0005(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C18 1.433(2) . ? O1 C23 1.433(2) . ? O2 C7 1.208(2) . ? O3 H3 0.8200 . ? O3 C18 1.405(2) . ? C7 C10 1.534(2) . ? C7 C21 1.504(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 C9 1.529(3) . ? C8 C10 1.536(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 C24 1.524(3) . ? C10 C13 1.555(2) . ? C10 C15 1.544(2) . ? C13 C19 1.531(2) . ? C13 C22 1.556(2) . ? C13 C26 1.546(2) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 C18 1.523(2) . ? C18 C24 1.511(3) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 C23 1.510(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 C22 1.524(2) . ? C22 H22 0.9800 . ? C22 C32 1.540(2) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C26 C30 1.527(3) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C30 C32 1.536(3) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? O4 C27 1.423(3) . ? O4 C29 1.417(3) . ? O5 C12 1.203(2) . ? O6 H6 0.8200 . ? O6 C29 1.419(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 C17 1.551(2) . ? C11 C29 1.517(2) . ? C12 C17 1.537(2) . ? C12 C31 1.503(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 C16 1.555(2) . ? C14 C35 1.525(3) . ? C16 C17 1.547(2) . ? C16 C20 1.555(2) . ? C16 C25 1.534(2) . ? C17 C28 1.532(2) . ? C20 H20 0.9800 . ? C20 C31 1.523(3) . ? C20 C36 1.530(3) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C25 C27 1.519(3) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 C34 1.526(3) . ? C29 C33 1.517(3) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C33 C34 1.531(3) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C35 C36 1.525(3) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C23 O1 C18 119.92(13) . . ? C18 O3 H3 109.5 . . ? O2 C7 C10 125.62(17) . . ? O2 C7 C21 124.23(16) . . ? C21 C7 C10 110.14(15) . . ? H8A C8 H8B 107.7 . . ? C9 C8 H8A 108.8 . . ? C9 C8 H8B 108.8 . . ? C9 C8 C10 113.61(15) . . ? C10 C8 H8A 108.8 . . ? C10 C8 H8B 108.8 . . ? C8 C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C24 C9 C8 111.18(14) . . ? C24 C9 H9A 109.4 . . ? C24 C9 H9B 109.4 . . ? C7 C10 C8 111.60(14) . . ? C7 C10 C13 100.54(13) . . ? C7 C10 C15 103.30(12) . . ? C8 C10 C13 117.22(13) . . ? C8 C10 C15 109.13(14) . . ? C15 C10 C13 113.88(14) . . ? C10 C13 C22 105.56(12) . . ? C19 C13 C10 117.62(14) . . ? C19 C13 C22 110.84(14) . . ? C19 C13 C26 109.62(14) . . ? C26 C13 C10 111.09(14) . . ? C26 C13 C22 100.74(13) . . ? C10 C15 H15A 108.7 . . ? C10 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C18 C15 C10 114.28(13) . . ? C18 C15 H15A 108.7 . . ? C18 C15 H15B 108.7 . . ? O1 C18 C15 114.38(14) . . ? O1 C18 C24 104.57(13) . . ? O3 C18 O1 109.22(15) . . ? O3 C18 C15 105.25(13) . . ? O3 C18 C24 112.25(15) . . ? C24 C18 C15 111.34(15) . . ? C13 C19 H19A 108.0 . . ? C13 C19 H19B 108.0 . . ? H19A C19 H19B 107.2 . . ? C23 C19 C13 117.17(15) . . ? C23 C19 H19A 108.0 . . ? C23 C19 H19B 108.0 . . ? C7 C21 H21A 110.4 . . ? C7 C21 H21B 110.4 . . ? C7 C21 C22 106.68(14) . . ? H21A C21 H21B 108.6 . . ? C22 C21 H21A 110.4 . . ? C22 C21 H21B 110.4 . . ? C13 C22 H22 110.8 . . ? C21 C22 C13 104.47(14) . . ? C21 C22 H22 110.8 . . ? C21 C22 C32 114.48(16) . . ? C32 C22 C13 105.19(14) . . ? C32 C22 H22 110.8 . . ? O1 C23 C19 111.27(16) . . ? O1 C23 H23A 109.4 . . ? O1 C23 H23B 109.4 . . ? C19 C23 H23A 109.4 . . ? C19 C23 H23B 109.4 . . ? H23A C23 H23B 108.0 . . ? C9 C24 H24A 109.6 . . ? C9 C24 H24B 109.6 . . ? C18 C24 C9 110.46(15) . . ? C18 C24 H24A 109.6 . . ? C18 C24 H24B 109.6 . . ? H24A C24 H24B 108.1 . . ? C13 C26 H26A 110.6 . . ? C13 C26 H26B 110.6 . . ? H26A C26 H26B 108.8 . . ? C30 C26 C13 105.59(16) . . ? C30 C26 H26A 110.6 . . ? C30 C26 H26B 110.6 . . ? C26 C30 H30A 110.6 . . ? C26 C30 H30B 110.6 . . ? C26 C30 C32 105.68(15) . . ? H30A C30 H30B 108.7 . . ? C32 C30 H30A 110.6 . . ? C32 C30 H30B 110.6 . . ? C22 C32 H32A 110.4 . . ? C22 C32 H32B 110.4 . . ? C30 C32 C22 106.54(16) . . ? C30 C32 H32A 110.4 . . ? C30 C32 H32B 110.4 . . ? H32A C32 H32B 108.6 . . ? C29 O4 C27 119.70(15) . . ? C29 O6 H6 109.5 . . ? H11A C11 H11B 107.6 . . ? C17 C11 H11A 108.6 . . ? C17 C11 H11B 108.6 . . ? C29 C11 H11A 108.6 . . ? C29 C11 H11B 108.6 . . ? C29 C11 C17 114.71(14) . . ? O5 C12 C17 125.05(18) . . ? O5 C12 C31 125.15(18) . . ? C31 C12 C17 109.80(15) . . ? H14A C14 H14B 108.6 . . ? C16 C14 H14A 110.3 . . ? C16 C14 H14B 110.3 . . ? C35 C14 H14A 110.3 . . ? C35 C14 H14B 110.3 . . ? C35 C14 C16 106.98(15) . . ? C14 C16 C20 100.85(14) . . ? C17 C16 C14 111.72(13) . . ? C17 C16 C20 105.10(14) . . ? C25 C16 C14 109.46(14) . . ? C25 C16 C17 116.64(15) . . ? C25 C16 C20 111.88(15) . . ? C12 C17 C11 102.35(13) . . ? C12 C17 C16 101.08(14) . . ? C16 C17 C11 113.32(13) . . ? C28 C17 C11 108.96(14) . . ? C28 C17 C12 111.62(15) . . ? C28 C17 C16 118.14(14) . . ? C16 C20 H20 110.7 . . ? C31 C20 C16 104.48(14) . . ? C31 C20 H20 110.7 . . ? C31 C20 C36 114.39(17) . . ? C36 C20 C16 105.47(15) . . ? C36 C20 H20 110.7 . . ? C16 C25 H25A 108.0 . . ? C16 C25 H25B 108.0 . . ? H25A C25 H25B 107.2 . . ? C27 C25 C16 117.17(15) . . ? C27 C25 H25A 108.0 . . ? C27 C25 H25B 108.0 . . ? O4 C27 C25 111.74(17) . . ? O4 C27 H27A 109.3 . . ? O4 C27 H27B 109.3 . . ? C25 C27 H27A 109.3 . . ? C25 C27 H27B 109.3 . . ? H27A C27 H27B 107.9 . . ? C17 C28 H28A 108.7 . . ? C17 C28 H28B 108.7 . . ? H28A C28 H28B 107.6 . . ? C34 C28 C17 114.42(16) . . ? C34 C28 H28A 108.7 . . ? C34 C28 H28B 108.7 . . ? O4 C29 O6 109.25(16) . . ? O4 C29 C11 115.04(16) . . ? O4 C29 C33 105.37(17) . . ? O6 C29 C11 104.43(15) . . ? O6 C29 C33 111.85(17) . . ? C33 C29 C11 111.05(17) . . ? C12 C31 C20 106.58(15) . . ? C12 C31 H31A 110.4 . . ? C12 C31 H31B 110.4 . . ? C20 C31 H31A 110.4 . . ? C20 C31 H31B 110.4 . . ? H31A C31 H31B 108.6 . . ? C29 C33 H33A 109.6 . . ? C29 C33 H33B 109.6 . . ? C29 C33 C34 110.46(18) . . ? H33A C33 H33B 108.1 . . ? C34 C33 H33A 109.6 . . ? C34 C33 H33B 109.6 . . ? C28 C34 C33 112.04(18) . . ? C28 C34 H34A 109.2 . . ? C28 C34 H34B 109.2 . . ? C33 C34 H34A 109.2 . . ? C33 C34 H34B 109.2 . . ? H34A C34 H34B 107.9 . . ? C14 C35 H35A 110.2 . . ? C14 C35 H35B 110.2 . . ? C14 C35 C36 107.33(16) . . ? H35A C35 H35B 108.5 . . ? C36 C35 H35A 110.2 . . ? C36 C35 H35B 110.2 . . ? C20 C36 H36A 110.7 . . ? C20 C36 H36B 110.7 . . ? C35 C36 C20 105.17(17) . . ? C35 C36 H36A 110.7 . . ? C35 C36 H36B 110.7 . . ? H36A C36 H36B 108.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C18 C24 C9 67.72(17) . . . . ? O2 C7 C10 C8 -29.6(2) . . . . ? O2 C7 C10 C13 -154.62(18) . . . . ? O2 C7 C10 C15 87.5(2) . . . . ? O2 C7 C21 C22 173.39(17) . . . . ? O3 C18 C24 C9 -174.00(14) . . . . ? C7 C10 C13 C19 -159.37(15) . . . . ? C7 C10 C13 C22 -35.15(16) . . . . ? C7 C10 C13 C26 73.19(16) . . . . ? C7 C10 C15 C18 -169.29(15) . . . . ? C7 C21 C22 C13 -14.63(18) . . . . ? C7 C21 C22 C32 -129.14(17) . . . . ? C8 C9 C24 C18 56.9(2) . . . . ? C8 C10 C13 C19 79.51(19) . . . . ? C8 C10 C13 C22 -156.26(14) . . . . ? C8 C10 C13 C26 -47.9(2) . . . . ? C8 C10 C15 C18 -50.45(19) . . . . ? C9 C8 C10 C7 164.34(14) . . . . ? C9 C8 C10 C13 -80.52(19) . . . . ? C9 C8 C10 C15 50.81(19) . . . . ? C10 C7 C21 C22 -7.9(2) . . . . ? C10 C8 C9 C24 -55.6(2) . . . . ? C10 C13 C19 C23 45.4(2) . . . . ? C10 C13 C22 C21 31.69(17) . . . . ? C10 C13 C22 C32 152.59(15) . . . . ? C10 C13 C26 C30 -151.01(15) . . . . ? C10 C15 C18 O1 -63.7(2) . . . . ? C10 C15 C18 O3 176.41(15) . . . . ? C10 C15 C18 C24 54.55(19) . . . . ? C13 C10 C15 C18 82.64(18) . . . . ? C13 C19 C23 O1 -77.8(2) . . . . ? C13 C22 C32 C30 -21.2(2) . . . . ? C13 C26 C30 C32 27.3(2) . . . . ? C15 C10 C13 C19 -49.60(19) . . . . ? C15 C10 C13 C22 74.62(16) . . . . ? C15 C10 C13 C26 -177.04(13) . . . . ? C15 C18 C24 C9 -56.29(19) . . . . ? C18 O1 C23 C19 83.4(2) . . . . ? C19 C13 C22 C21 160.07(14) . . . . ? C19 C13 C22 C32 -79.03(18) . . . . ? C19 C13 C26 C30 77.31(19) . . . . ? C21 C7 C10 C8 151.74(15) . . . . ? C21 C7 C10 C13 26.70(17) . . . . ? C21 C7 C10 C15 -91.14(16) . . . . ? C21 C22 C32 C30 92.9(2) . . . . ? C22 C13 C19 C23 -76.10(19) . . . . ? C22 C13 C26 C30 -39.56(18) . . . . ? C23 O1 C18 O3 101.39(17) . . . . ? C23 O1 C18 C15 -16.2(2) . . . . ? C23 O1 C18 C24 -138.29(16) . . . . ? C26 C13 C19 C23 173.58(16) . . . . ? C26 C13 C22 C21 -83.96(16) . . . . ? C26 C13 C22 C32 36.93(18) . . . . ? C26 C30 C32 C22 -3.6(2) . . . . ? O4 C29 C33 C34 -69.2(2) . . . . ? O5 C12 C17 C11 -87.3(2) . . . . ? O5 C12 C17 C16 155.60(17) . . . . ? O5 C12 C17 C28 29.1(2) . . . . ? O5 C12 C31 C20 -175.47(17) . . . . ? O6 C29 C33 C34 172.18(19) . . . . ? C11 C17 C28 C34 -49.2(2) . . . . ? C11 C29 C33 C34 55.9(3) . . . . ? C12 C17 C28 C34 -161.48(17) . . . . ? C14 C16 C17 C11 178.09(15) . . . . ? C14 C16 C17 C12 -73.14(17) . . . . ? C14 C16 C17 C28 48.9(2) . . . . ? C14 C16 C20 C31 83.12(16) . . . . ? C14 C16 C20 C36 -37.81(18) . . . . ? C14 C16 C25 C27 -175.61(17) . . . . ? C14 C35 C36 C20 -11.2(3) . . . . ? C16 C14 C35 C36 -12.8(3) . . . . ? C16 C17 C28 C34 82.0(2) . . . . ? C16 C20 C31 C12 16.76(18) . . . . ? C16 C20 C36 C35 31.1(2) . . . . ? C16 C25 C27 O4 78.9(2) . . . . ? C17 C11 C29 O4 64.1(2) . . . . ? C17 C11 C29 O6 -176.21(15) . . . . ? C17 C11 C29 C33 -55.5(2) . . . . ? C17 C12 C31 C20 5.73(19) . . . . ? C17 C16 C20 C31 -33.11(16) . . . . ? C17 C16 C20 C36 -154.04(15) . . . . ? C17 C16 C25 C27 -47.6(2) . . . . ? C17 C28 C34 C33 53.4(3) . . . . ? C20 C16 C17 C11 -73.40(17) . . . . ? C20 C16 C17 C12 35.37(15) . . . . ? C20 C16 C17 C28 157.41(15) . . . . ? C20 C16 C25 C27 73.5(2) . . . . ? C25 C16 C17 C11 51.1(2) . . . . ? C25 C16 C17 C12 159.92(14) . . . . ? C25 C16 C17 C28 -78.04(19) . . . . ? C25 C16 C20 C31 -160.62(15) . . . . ? C25 C16 C20 C36 78.46(18) . . . . ? C27 O4 C29 O6 -101.76(18) . . . . ? C27 O4 C29 C11 15.3(2) . . . . ? C27 O4 C29 C33 137.93(16) . . . . ? C29 O4 C27 C25 -82.1(2) . . . . ? C29 C11 C17 C12 168.93(16) . . . . ? C29 C11 C17 C16 -83.10(19) . . . . ? C29 C11 C17 C28 50.6(2) . . . . ? C29 C33 C34 C28 -55.2(3) . . . . ? C31 C12 C17 C11 91.51(16) . . . . ? C31 C12 C17 C16 -25.60(17) . . . . ? C31 C12 C17 C28 -152.09(15) . . . . ? C31 C20 C36 C35 -83.2(2) . . . . ? C35 C14 C16 C17 141.97(18) . . . . ? C35 C14 C16 C20 30.8(2) . . . . ? C35 C14 C16 C25 -87.3(2) . . . . ? C36 C20 C31 C12 131.57(17) . . . . ? _shelx_res_file ; TITL zhangye_1015 in P21/n #14 zhangye_1015.res created by SHELXL-2018/3 at 15:09:35 on 18-Oct-2019 REM reset to P21/n #14 CELL 1.54184 7.668763 22.430483 15.474682 90 101.3287 90 ZERR 4 0.000269 0.000553 0.000484 0 0.0035 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H O UNIT 120 176 24 L.S. 20 PLAN 20 BOND $H HTAB CONF fmap 2 acta SHEL 999 0.84 REM REM REM WGHT 0.070300 0.483500 FVAR 9.46969 O1 3 0.047533 0.032778 0.604094 11.00000 0.04446 0.04994 = 0.04046 0.00507 0.00172 0.00468 O2 3 0.536916 -0.051585 0.875369 11.00000 0.05764 0.06879 = 0.04765 0.00124 0.00077 0.02735 O3 3 0.100643 -0.064663 0.567497 11.00000 0.08817 0.04183 = 0.03869 -0.00185 -0.00270 -0.01199 AFIX 147 H3 2 0.056875 -0.054452 0.517014 11.00000 -1.50000 AFIX 0 C7 1 0.396210 -0.025651 0.859178 11.00000 0.04597 0.03571 = 0.03977 -0.00430 0.00100 0.00581 C8 1 0.478061 0.037999 0.737452 11.00000 0.03243 0.04487 = 0.05887 0.00025 0.00743 -0.00173 AFIX 23 H8A 2 0.527818 0.071247 0.774264 11.00000 -1.20000 H8B 2 0.571101 0.008429 0.739567 11.00000 -1.20000 AFIX 0 C9 1 0.420693 0.059884 0.642562 11.00000 0.04148 0.04422 = 0.06558 0.01125 0.01853 -0.00200 AFIX 23 H9A 2 0.338114 0.092808 0.640972 11.00000 -1.20000 H9B 2 0.523896 0.074322 0.621361 11.00000 -1.20000 AFIX 0 C10 1 0.325831 0.010602 0.775582 11.00000 0.03278 0.02952 = 0.04140 -0.00013 0.00295 0.00021 C13 1 0.198484 0.054380 0.810476 11.00000 0.03673 0.02750 = 0.04416 -0.00180 0.00657 -0.00041 C15 1 0.229228 -0.036553 0.710655 11.00000 0.04424 0.02919 = 0.03745 0.00046 0.00554 -0.00093 AFIX 23 H15A 2 0.306477 -0.070890 0.711616 11.00000 -1.20000 H15B 2 0.123524 -0.049578 0.730936 11.00000 -1.20000 AFIX 0 C18 1 0.174999 -0.014737 0.615978 11.00000 0.04983 0.03299 = 0.03832 0.00090 0.00243 0.00015 C19 1 0.052638 0.084389 0.742631 11.00000 0.04573 0.04130 = 0.05373 0.00423 0.01182 0.01273 AFIX 23 H19A 2 -0.030664 0.102970 0.774086 11.00000 -1.20000 H19B 2 0.107142 0.116015 0.714376 11.00000 -1.20000 AFIX 0 C21 1 0.262233 -0.025710 0.918294 11.00000 0.06176 0.04429 = 0.04627 0.00620 0.01394 0.00769 AFIX 23 H21A 2 0.317604 -0.013353 0.977391 11.00000 -1.20000 H21B 2 0.213043 -0.065325 0.921286 11.00000 -1.20000 AFIX 0 C22 1 0.116566 0.018045 0.878387 11.00000 0.04330 0.03553 = 0.04599 -0.00240 0.01121 -0.00254 AFIX 13 H22 2 0.009532 -0.003212 0.849092 11.00000 -1.20000 AFIX 0 C23 1 -0.051803 0.045276 0.671331 11.00000 0.03385 0.06710 = 0.05352 0.00762 0.00372 0.00797 AFIX 23 H23A 2 -0.081435 0.008130 0.697130 11.00000 -1.20000 H23B 2 -0.162053 0.065076 0.645251 11.00000 -1.20000 AFIX 0 C24 1 0.332353 0.010155 0.582402 11.00000 0.05425 0.04718 = 0.04596 0.00851 0.01531 0.00849 AFIX 23 H24A 2 0.292982 0.025557 0.523209 11.00000 -1.20000 H24B 2 0.417799 -0.021386 0.579993 11.00000 -1.20000 AFIX 0 C26 1 0.303993 0.102228 0.871111 11.00000 0.05664 0.03301 = 0.05842 -0.00925 0.01149 -0.00795 AFIX 23 H26A 2 0.416412 0.086208 0.902203 11.00000 -1.20000 H26B 2 0.327542 0.136549 0.837025 11.00000 -1.20000 AFIX 0 C30 1 0.186008 0.119600 0.935927 11.00000 0.08432 0.04196 = 0.06360 -0.01464 0.02268 0.00002 AFIX 23 H30A 2 0.112043 0.153546 0.914018 11.00000 -1.20000 H30B 2 0.257901 0.129797 0.992829 11.00000 -1.20000 AFIX 0 C32 1 0.070759 0.064588 0.943652 11.00000 0.06900 0.04956 = 0.05857 -0.00479 0.02679 0.00337 AFIX 23 H32A 2 -0.054439 0.074855 0.928865 11.00000 -1.20000 H32B 2 0.096833 0.049025 1.003284 11.00000 -1.20000 AFIX 0 O4 3 0.414182 0.146555 0.319478 11.00000 0.04181 0.05280 = 0.08612 -0.00913 0.02308 0.00226 O5 3 -0.215440 0.254591 0.309983 11.00000 0.04059 0.06933 = 0.08003 -0.00593 -0.00887 0.01435 O6 3 0.205299 0.091459 0.223962 11.00000 0.06873 0.04390 = 0.08354 -0.02257 0.03311 -0.00903 AFIX 147 H6 2 0.282930 0.080697 0.197732 11.00000 -1.50000 AFIX 0 C11 1 0.091024 0.165073 0.302491 11.00000 0.03594 0.03372 = 0.05011 -0.00420 0.00682 -0.00328 AFIX 23 H11A 2 0.084068 0.136396 0.348611 11.00000 -1.20000 H11B 2 -0.017252 0.161533 0.258264 11.00000 -1.20000 AFIX 0 C12 1 -0.088871 0.236223 0.361726 11.00000 0.03292 0.03253 = 0.06334 -0.00860 -0.00167 0.00254 C14 1 0.223237 0.297001 0.473242 11.00000 0.04501 0.03105 = 0.06615 -0.00648 0.00428 -0.00207 AFIX 23 H14A 2 0.332631 0.316049 0.465416 11.00000 -1.20000 H14B 2 0.123611 0.320310 0.442469 11.00000 -1.20000 AFIX 0 C16 1 0.213370 0.232275 0.436673 11.00000 0.03226 0.02819 = 0.05252 -0.00218 0.00324 -0.00076 C17 1 0.099068 0.228622 0.342585 11.00000 0.03247 0.02965 = 0.05139 -0.00196 0.00316 0.00022 C20 1 0.099943 0.201575 0.496911 11.00000 0.04608 0.03440 = 0.05273 -0.00040 0.01069 -0.00064 AFIX 13 H20 2 0.119719 0.158390 0.498787 11.00000 -1.20000 AFIX 0 C25 1 0.401377 0.206025 0.449797 11.00000 0.03181 0.04332 = 0.07200 -0.00450 -0.00246 0.00082 AFIX 23 H25A 2 0.474754 0.233360 0.423956 11.00000 -1.20000 H25B 2 0.449596 0.204560 0.512592 11.00000 -1.20000 AFIX 0 C27 1 0.420242 0.144420 0.411938 11.00000 0.03711 0.04390 = 0.08156 -0.00148 0.00253 0.01022 AFIX 23 H27A 2 0.532319 0.127034 0.440964 11.00000 -1.20000 H27B 2 0.325124 0.119034 0.423630 11.00000 -1.20000 AFIX 0 C28 1 0.135816 0.273563 0.273767 11.00000 0.05999 0.03622 = 0.05790 0.00531 0.00786 0.00098 AFIX 23 H28A 2 0.029438 0.277540 0.228425 11.00000 -1.20000 H28B 2 0.160021 0.312135 0.301908 11.00000 -1.20000 AFIX 0 C29 1 0.247668 0.148911 0.260574 11.00000 0.04839 0.03652 = 0.06544 -0.00900 0.02060 -0.00451 C31 1 -0.091617 0.216046 0.454084 11.00000 0.04115 0.04866 = 0.07377 -0.00328 0.01894 -0.00248 AFIX 23 H31A 2 -0.166140 0.181022 0.453203 11.00000 -1.20000 H31B 2 -0.137884 0.247356 0.486512 11.00000 -1.20000 AFIX 0 C33 1 0.271088 0.194075 0.190813 11.00000 0.08191 0.05698 = 0.07144 -0.00251 0.04002 -0.00568 AFIX 23 H33A 2 0.168779 0.192759 0.142720 11.00000 -1.20000 H33B 2 0.375843 0.184122 0.167394 11.00000 -1.20000 AFIX 0 C34 1 0.290979 0.256939 0.230032 11.00000 0.07867 0.04697 = 0.07774 0.00857 0.03263 -0.00972 AFIX 23 H34A 2 0.400998 0.259281 0.273295 11.00000 -1.20000 H34B 2 0.298058 0.285412 0.183668 11.00000 -1.20000 AFIX 0 C35 1 0.217265 0.292624 0.570954 11.00000 0.09780 0.05478 = 0.06675 -0.01895 0.01490 -0.01242 AFIX 23 H35A 2 0.132274 0.320954 0.585861 11.00000 -1.20000 H35B 2 0.333350 0.301357 0.606486 11.00000 -1.20000 AFIX 0 C36 1 0.161697 0.229130 0.588237 11.00000 0.07591 0.05545 = 0.05376 -0.00504 0.01032 -0.00051 AFIX 23 H36A 2 0.065838 0.229315 0.620851 11.00000 -1.20000 H36B 2 0.261210 0.206997 0.621625 11.00000 -1.20000 AFIX 0 HKLF 4 REM zhangye_1015 in P21/n #14 REM wR2 = 0.1371, GooF = S = 1.063, Restrained GooF = 1.063 for all data REM R1 = 0.0456 for 3722 Fo > 4sig(Fo) and 0.0551 for all 4422 data REM 327 parameters refined using 0 restraints END WGHT 0.0703 0.4836 REM Instructions for potential hydrogen bonds EQIV $1 -x, -y, -z+1 HTAB O3 O1_$1 EQIV $2 -x+1, -y, -z+1 HTAB O6 O2_$2 HTAB C11 O3_$1 REM Highest difference peak 0.279, deepest hole -0.175, 1-sigma level 0.040 Q1 1 0.2685 0.0323 0.7942 11.00000 0.05 0.28 Q2 1 0.3408 -0.0013 0.8185 11.00000 0.05 0.19 Q3 1 0.1533 0.0371 0.8420 11.00000 0.05 0.19 Q4 1 0.1114 0.2480 0.3068 11.00000 0.05 0.17 Q5 1 0.1814 -0.0237 0.6658 11.00000 0.05 0.17 Q6 1 0.2091 0.2608 0.4422 11.00000 0.05 0.16 Q7 1 0.0112 0.2087 0.4673 11.00000 0.05 0.16 Q8 1 0.2012 -0.0023 0.8934 11.00000 0.05 0.15 Q9 1 0.1903 -0.0438 0.5788 11.00000 0.05 0.15 Q10 1 0.1618 0.2317 0.3933 11.00000 0.05 0.15 Q11 1 0.0356 0.2397 0.3625 11.00000 0.05 0.15 Q12 1 0.1251 0.0892 0.9365 11.00000 0.05 0.15 Q13 1 0.1447 0.0637 0.7736 11.00000 0.05 0.14 Q14 1 0.0180 -0.0434 0.5956 11.00000 0.05 0.14 Q15 1 0.0789 0.2410 0.3775 11.00000 0.05 0.14 Q16 1 0.2557 0.0759 0.8288 11.00000 0.05 0.14 Q17 1 0.2831 0.2193 0.4405 11.00000 0.05 0.14 Q18 1 0.1021 0.0353 0.9143 11.00000 0.05 0.14 Q19 1 0.1082 0.1981 0.3230 11.00000 0.05 0.14 Q20 1 0.2564 -0.0008 0.6024 11.00000 0.05 0.14 ; _shelx_res_checksum 66820 _olex2_date_sample_data_collection 2019-10-16 _olex2_submission_special_instructions 'No special instructions were received' ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_zhangy_1028 _database_code_depnum_ccdc_archive 'CCDC 1962417' loop_ _audit_author_name _audit_author_address 'YE ZHANG' ;LANZHOU UNIVERSITY China ; _audit_update_record ; 2019-10-30 deposited with the CCDC. 2020-03-11 downloaded from the CCDC. ; _audit_creation_date 2019-10-30 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _shelx_SHELXL_version_number 2018/3 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C12 H20 O2' _chemical_formula_sum 'C12 H20 O2' _chemical_formula_weight 196.28 _chemical_melting_point ? _chemical_oxdiff_formula 'pd F S C' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.1285(3) _cell_length_b 11.9273(4) _cell_length_c 13.4833(5) _cell_angle_alpha 90 _cell_angle_beta 104.629(4) _cell_angle_gamma 90 _cell_volume 1109.23(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2260 _cell_measurement_temperature 294.06(10) _cell_measurement_theta_max 69.2990 _cell_measurement_theta_min 5.0330 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _exptl_absorpt_coefficient_mu 0.613 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.70498 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.175 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_F_000 432 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_unetI/netI 0.0186 _diffrn_reflns_Laue_measured_fraction_full 0.966 _diffrn_reflns_Laue_measured_fraction_max 0.966 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 4576 _diffrn_reflns_point_group_measured_fraction_full 0.966 _diffrn_reflns_point_group_measured_fraction_max 0.966 _diffrn_reflns_theta_full 66.588 _diffrn_reflns_theta_max 66.588 _diffrn_reflns_theta_min 5.024 _diffrn_ambient_temperature 294.06(10) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.966 _diffrn_measured_fraction_theta_max 0.966 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 14.00 39.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 50.0000 -150.0000 25 #__ type_ start__ end____ width___ exp.time_ 2 omega -87.00 -54.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 178.0000 -60.0000 33 #__ type_ start__ end____ width___ exp.time_ 3 omega -74.00 -35.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 178.0000 120.0000 39 #__ type_ start__ end____ width___ exp.time_ 4 omega 38.00 63.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -125.0000 90.0000 25 #__ type_ start__ end____ width___ exp.time_ 5 omega -19.00 80.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -38.0000 -180.0000 99 #__ type_ start__ end____ width___ exp.time_ 6 omega 66.00 97.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -125.0000 90.0000 31 #__ type_ start__ end____ width___ exp.time_ 7 omega 35.00 112.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 0.0000 77 #__ type_ start__ end____ width___ exp.time_ 8 omega 41.00 84.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -38.0000 120.0000 43 #__ type_ start__ end____ width___ exp.time_ 9 omega 34.00 92.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 60.0000 58 #__ type_ start__ end____ width___ exp.time_ 10 omega 92.00 137.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -91.0000 90.0000 45 #__ type_ start__ end____ width___ exp.time_ 11 omega 49.00 75.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -50.0000 60.0000 26 #__ type_ start__ end____ width___ exp.time_ 12 omega 36.00 77.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -38.0000 0.0000 41 #__ type_ start__ end____ width___ exp.time_ 13 omega 45.00 87.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 0.0000 42 #__ type_ start__ end____ width___ exp.time_ 14 omega 44.00 80.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -50.0000 -150.0000 36 #__ type_ start__ end____ width___ exp.time_ 15 omega 66.00 91.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -38.0000 -120.0000 25 #__ type_ start__ end____ width___ exp.time_ 16 omega 101.00 151.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 178.0000 -150.0000 50 #__ type_ start__ end____ width___ exp.time_ 17 omega 71.00 97.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 178.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 18 omega 47.00 83.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 -150.0000 36 #__ type_ start__ end____ width___ exp.time_ 19 omega 40.00 80.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -50.0000 -180.0000 40 #__ type_ start__ end____ width___ exp.time_ 20 omega 49.00 101.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -50.0000 -60.0000 52 #__ type_ start__ end____ width___ exp.time_ 21 omega -16.00 10.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 -57.0000 -30.0000 26 #__ type_ start__ end____ width___ exp.time_ 22 omega -65.00 -40.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 125.0000 30.0000 25 #__ type_ start__ end____ width___ exp.time_ 23 omega 81.00 112.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 38.0000 60.0000 31 #__ type_ start__ end____ width___ exp.time_ 24 omega 40.00 66.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 38.0000 60.0000 26 #__ type_ start__ end____ width___ exp.time_ 25 omega 106.00 138.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 111.0000 150.0000 32 #__ type_ start__ end____ width___ exp.time_ 26 omega 78.00 113.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 30.0000 35 #__ type_ start__ end____ width___ exp.time_ 27 omega 53.00 78.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 -120.0000 25 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0827620000 _diffrn_orient_matrix_UB_12 0.1160422000 _diffrn_orient_matrix_UB_13 -0.0380275000 _diffrn_orient_matrix_UB_21 0.2060353000 _diffrn_orient_matrix_UB_22 0.0419976000 _diffrn_orient_matrix_UB_23 0.0036125000 _diffrn_orient_matrix_UB_31 -0.0247053000 _diffrn_orient_matrix_UB_32 -0.0381086000 _diffrn_orient_matrix_UB_33 -0.1116959000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_source 'SuperNova (Cu) X-ray Source' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1711 _reflns_number_total 1899 _reflns_odcompleteness_completeness 96.19 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.228 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.033 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 144 _refine_ls_number_reflns 1899 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0424 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+0.2960P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1158 _refine_ls_wR_factor_ref 0.1188 _refine_special_details ? _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C4(H4) 2.b Secondary CH2 refined with riding coordinates: C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B) 2.c Idealised Me refined as rotating group: C11(H11A,H11B,H11C) ; _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary ? loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.44077(17) 0.62534(9) 0.08951(8) 0.0433(3) Uani 1 1 d . . . . . H1 H 0.412(3) 0.558(2) 0.0971(16) 0.066(6) Uiso 1 1 d . . . . . O2 O 0.58071(19) 0.88976(9) 0.40995(8) 0.0494(3) Uani 1 1 d . . . . . H2 H 0.533(3) 0.8780(18) 0.4585(18) 0.070(7) Uiso 1 1 d . . . . . C1 C 0.3009(2) 0.58137(11) 0.27082(11) 0.0349(3) Uani 1 1 d . . . . . H1A H 0.413465 0.547926 0.254469 0.042 Uiso 1 1 calc R . . . . H1B H 0.329026 0.591966 0.344438 0.042 Uiso 1 1 calc R . . . . C2 C 0.1238(2) 0.50517(13) 0.23447(15) 0.0509(4) Uani 1 1 d . . . . . H2A H 0.133102 0.462047 0.174894 0.061 Uiso 1 1 calc R . . . . H2B H 0.111613 0.453949 0.288365 0.061 Uiso 1 1 calc R . . . . C3 C -0.0473(2) 0.58567(16) 0.20773(16) 0.0586(5) Uani 1 1 d . . . . . H3A H -0.156718 0.552219 0.158970 0.070 Uiso 1 1 calc R . . . . H3B H -0.087314 0.607740 0.268534 0.070 Uiso 1 1 calc R . . . . C4 C 0.0323(2) 0.68505(14) 0.16090(13) 0.0448(4) Uani 1 1 d . . . . . H4 H -0.040421 0.754626 0.161719 0.054 Uiso 1 1 calc R . . . . C5 C 0.25281(19) 0.69514(11) 0.21518(10) 0.0299(3) Uani 1 1 d . . . . . C6 C 0.2951(2) 0.69926(11) 0.10509(10) 0.0322(3) Uani 1 1 d . . . . . C7 C 0.0837(2) 0.66283(16) 0.05830(13) 0.0518(4) Uani 1 1 d . . . . . H7A H 0.014947 0.711054 0.003079 0.062 Uiso 1 1 calc R . . . . H7B H 0.070974 0.584773 0.037495 0.062 Uiso 1 1 calc R . . . . C8 C 0.3174(2) 0.79345(12) 0.28855(11) 0.0361(3) Uani 1 1 d . . . . . H8A H 0.278564 0.862603 0.251129 0.043 Uiso 1 1 calc R . . . . H8B H 0.248913 0.789223 0.342115 0.043 Uiso 1 1 calc R . . . . C9 C 0.5325(2) 0.79935(12) 0.33841(11) 0.0388(4) Uani 1 1 d . . . . . H9A H 0.574174 0.729272 0.373625 0.047 Uiso 1 1 calc R . . . . H9B H 0.602093 0.808617 0.285716 0.047 Uiso 1 1 calc R . . . . C10 C 0.3455(2) 0.81522(11) 0.07378(10) 0.0357(3) Uani 1 1 d . . . . . C11 C 0.1896(3) 0.90239(16) 0.04682(15) 0.0599(5) Uani 1 1 d . . . . . H11A H 0.109239 0.887871 -0.020597 0.090 Uiso 1 1 calc GR . . . . H11B H 0.247701 0.975186 0.048244 0.090 Uiso 1 1 calc GR . . . . H11C H 0.112057 0.899988 0.095543 0.090 Uiso 1 1 calc GR . . . . C12 C 0.5248(2) 0.84009(14) 0.06955(12) 0.0427(4) Uani 1 1 d . . . . . H12A H 0.558(3) 0.9160(16) 0.0501(14) 0.052(5) Uiso 1 1 d . . . . . H12B H 0.625(3) 0.7847(17) 0.0879(16) 0.062(6) Uiso 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0602(7) 0.0295(6) 0.0472(6) -0.0002(4) 0.0265(5) 0.0088(5) O2 0.0739(8) 0.0398(6) 0.0368(6) -0.0088(4) 0.0182(6) -0.0184(5) C1 0.0397(8) 0.0306(7) 0.0361(7) 0.0044(6) 0.0129(6) 0.0006(6) C2 0.0488(9) 0.0366(9) 0.0686(11) 0.0071(7) 0.0171(8) -0.0083(7) C3 0.0381(9) 0.0581(11) 0.0825(13) 0.0064(9) 0.0209(8) -0.0078(8) C4 0.0297(7) 0.0431(9) 0.0600(10) 0.0050(7) 0.0086(7) 0.0026(6) C5 0.0302(7) 0.0285(7) 0.0325(7) 0.0013(5) 0.0105(5) 0.0019(5) C6 0.0370(7) 0.0304(7) 0.0288(7) -0.0010(5) 0.0075(5) 0.0031(5) C7 0.0480(9) 0.0555(10) 0.0436(9) 0.0005(8) -0.0038(7) -0.0095(8) C8 0.0466(8) 0.0306(7) 0.0348(7) -0.0009(5) 0.0173(6) 0.0033(6) C9 0.0511(9) 0.0338(7) 0.0330(7) -0.0044(6) 0.0132(6) -0.0053(6) C10 0.0489(8) 0.0321(7) 0.0267(6) 0.0028(5) 0.0105(6) 0.0065(6) C11 0.0711(12) 0.0500(10) 0.0654(12) 0.0245(9) 0.0297(10) 0.0253(9) C12 0.0516(9) 0.0360(8) 0.0405(8) 0.0019(6) 0.0115(7) -0.0047(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 H1 0.84(2) . ? O1 C6 1.4178(17) . ? O2 H2 0.82(2) . ? O2 C9 1.4297(17) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C1 C2 1.532(2) . ? C1 C5 1.5465(18) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C2 C3 1.522(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 C4 1.519(2) . ? C4 H4 0.9800 . ? C4 C5 1.5621(19) . ? C4 C7 1.541(2) . ? C5 C6 1.5882(18) . ? C5 C8 1.5283(18) . ? C6 C7 1.542(2) . ? C6 C10 1.5155(19) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 C9 1.513(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.498(2) . ? C10 C12 1.327(2) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.989(19) . ? C12 H12B 0.96(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O1 H1 111.4(15) . . ? C9 O2 H2 109.4(16) . . ? H1A C1 H1B 108.5 . . ? C2 C1 H1A 110.2 . . ? C2 C1 H1B 110.2 . . ? C2 C1 C5 107.55(12) . . ? C5 C1 H1A 110.2 . . ? C5 C1 H1B 110.2 . . ? C1 C2 H2A 110.9 . . ? C1 C2 H2B 110.9 . . ? H2A C2 H2B 108.9 . . ? C3 C2 C1 104.34(13) . . ? C3 C2 H2A 110.9 . . ? C3 C2 H2B 110.9 . . ? C2 C3 H3A 111.1 . . ? C2 C3 H3B 111.1 . . ? H3A C3 H3B 109.1 . . ? C4 C3 C2 103.27(13) . . ? C4 C3 H3A 111.1 . . ? C4 C3 H3B 111.1 . . ? C3 C4 H4 113.7 . . ? C3 C4 C5 107.62(13) . . ? C3 C4 C7 115.95(15) . . ? C5 C4 H4 113.7 . . ? C7 C4 H4 113.7 . . ? C7 C4 C5 89.70(11) . . ? C1 C5 C4 103.49(11) . . ? C1 C5 C6 114.17(11) . . ? C4 C5 C6 88.31(11) . . ? C8 C5 C1 111.44(11) . . ? C8 C5 C4 117.74(11) . . ? C8 C5 C6 118.94(11) . . ? O1 C6 C5 115.98(11) . . ? O1 C6 C7 116.17(12) . . ? O1 C6 C10 106.99(11) . . ? C7 C6 C5 88.69(11) . . ? C10 C6 C5 113.76(11) . . ? C10 C6 C7 114.78(12) . . ? C4 C7 C6 90.78(11) . . ? C4 C7 H7A 113.5 . . ? C4 C7 H7B 113.5 . . ? C6 C7 H7A 113.5 . . ? C6 C7 H7B 113.5 . . ? H7A C7 H7B 110.8 . . ? C5 C8 H8A 108.4 . . ? C5 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? C9 C8 C5 115.43(11) . . ? C9 C8 H8A 108.4 . . ? C9 C8 H8B 108.4 . . ? O2 C9 C8 112.26(12) . . ? O2 C9 H9A 109.2 . . ? O2 C9 H9B 109.2 . . ? C8 C9 H9A 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C11 C10 C6 119.19(14) . . ? C12 C10 C6 120.96(13) . . ? C12 C10 C11 119.85(15) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 121.1(11) . . ? C10 C12 H12B 119.9(12) . . ? H12A C12 H12B 118.9(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C6 C7 C4 130.52(13) . . . . ? O1 C6 C10 C11 158.99(14) . . . . ? O1 C6 C10 C12 -20.71(17) . . . . ? C1 C2 C3 C4 37.21(19) . . . . ? C1 C5 C6 O1 -26.49(17) . . . . ? C1 C5 C6 C7 92.17(13) . . . . ? C1 C5 C6 C10 -151.21(12) . . . . ? C1 C5 C8 C9 61.00(15) . . . . ? C2 C1 C5 C4 8.79(15) . . . . ? C2 C1 C5 C6 -85.47(14) . . . . ? C2 C1 C5 C8 136.27(13) . . . . ? C2 C3 C4 C5 -32.41(19) . . . . ? C2 C3 C4 C7 66.13(19) . . . . ? C3 C4 C5 C1 14.62(16) . . . . ? C3 C4 C5 C6 129.09(14) . . . . ? C3 C4 C5 C8 -108.81(15) . . . . ? C3 C4 C7 C6 -121.74(14) . . . . ? C4 C5 C6 O1 -130.52(12) . . . . ? C4 C5 C6 C7 -11.86(11) . . . . ? C4 C5 C6 C10 104.75(13) . . . . ? C4 C5 C8 C9 -179.67(12) . . . . ? C5 C1 C2 C3 -28.84(17) . . . . ? C5 C4 C7 C6 -12.22(12) . . . . ? C5 C6 C7 C4 12.02(11) . . . . ? C5 C6 C10 C11 -71.59(17) . . . . ? C5 C6 C10 C12 108.71(15) . . . . ? C5 C8 C9 O2 -176.90(11) . . . . ? C6 C5 C8 C9 -75.04(16) . . . . ? C7 C4 C5 C1 -102.60(12) . . . . ? C7 C4 C5 C6 11.87(11) . . . . ? C7 C4 C5 C8 133.97(13) . . . . ? C7 C6 C10 C11 28.52(19) . . . . ? C7 C6 C10 C12 -151.17(14) . . . . ? C8 C5 C6 O1 108.43(14) . . . . ? C8 C5 C6 C7 -132.91(13) . . . . ? C8 C5 C6 C10 -16.30(17) . . . . ? C10 C6 C7 C4 -103.65(13) . . . . ? _shelx_res_file ; TITL zhangy_1028 in P21/c #14 zhangy_1028.res created by SHELXL-2018/3 at 15:16:16 on 30-Oct-2019 REM reset to P21/c #14 CELL 1.54184 7.128513 11.927255 13.483263 90 104.6285 90 ZERR 4 0.000299 0.000418 0.000457 0 0.0039 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H O UNIT 48 80 8 L.S. 10 PLAN 20 BOND $H HTAB CONF fmap 2 acta SHEL 999 0.84 REM REM REM WGHT 0.059000 0.296000 FVAR 14.65504 O1 3 0.440765 0.625342 0.089511 11.00000 0.06020 0.02951 = 0.04719 -0.00021 0.02650 0.00884 H1 2 0.411950 0.557985 0.097080 11.00000 0.06628 O2 3 0.580708 0.889765 0.409949 11.00000 0.07388 0.03983 = 0.03677 -0.00880 0.01818 -0.01841 H2 2 0.533079 0.878023 0.458498 11.00000 0.06978 C1 1 0.300906 0.581372 0.270821 11.00000 0.03975 0.03060 = 0.03615 0.00441 0.01295 0.00060 AFIX 23 H1A 2 0.413465 0.547926 0.254469 11.00000 -1.20000 H1B 2 0.329026 0.591966 0.344438 11.00000 -1.20000 AFIX 0 C2 1 0.123821 0.505169 0.234465 11.00000 0.04875 0.03656 = 0.06862 0.00712 0.01709 -0.00826 AFIX 23 H2A 2 0.133102 0.462047 0.174894 11.00000 -1.20000 H2B 2 0.111613 0.453949 0.288365 11.00000 -1.20000 AFIX 0 C3 1 -0.047292 0.585672 0.207732 11.00000 0.03810 0.05809 = 0.08253 0.00642 0.02089 -0.00782 AFIX 23 H3A 2 -0.156718 0.552219 0.158970 11.00000 -1.20000 H3B 2 -0.087314 0.607740 0.268534 11.00000 -1.20000 AFIX 0 C4 1 0.032293 0.685047 0.160900 11.00000 0.02974 0.04310 = 0.06003 0.00497 0.00864 0.00261 AFIX 13 H4 2 -0.040421 0.754626 0.161719 11.00000 -1.20000 AFIX 0 C5 1 0.252815 0.695136 0.215180 11.00000 0.03016 0.02846 = 0.03254 0.00135 0.01046 0.00194 C6 1 0.295070 0.699259 0.105085 11.00000 0.03700 0.03038 = 0.02878 -0.00097 0.00746 0.00309 C7 1 0.083657 0.662833 0.058302 11.00000 0.04795 0.05553 = 0.04362 0.00049 -0.00382 -0.00947 AFIX 23 H7A 2 0.014947 0.711054 0.003079 11.00000 -1.20000 H7B 2 0.070974 0.584773 0.037495 11.00000 -1.20000 AFIX 0 C8 1 0.317422 0.793453 0.288546 11.00000 0.04662 0.03065 = 0.03482 -0.00090 0.01733 0.00331 AFIX 23 H8A 2 0.278564 0.862603 0.251129 11.00000 -1.20000 H8B 2 0.248913 0.789223 0.342115 11.00000 -1.20000 AFIX 0 C9 1 0.532535 0.799348 0.338414 11.00000 0.05105 0.03379 = 0.03295 -0.00444 0.01317 -0.00527 AFIX 23 H9A 2 0.574174 0.729272 0.373625 11.00000 -1.20000 H9B 2 0.602093 0.808617 0.285716 11.00000 -1.20000 AFIX 0 C10 1 0.345461 0.815217 0.073777 11.00000 0.04889 0.03212 = 0.02668 0.00278 0.01051 0.00651 C11 1 0.189627 0.902390 0.046822 11.00000 0.07107 0.04998 = 0.06543 0.02452 0.02972 0.02530 AFIX 137 H11A 2 0.109239 0.887871 -0.020597 11.00000 -1.50000 H11B 2 0.247701 0.975186 0.048244 11.00000 -1.50000 H11C 2 0.112057 0.899988 0.095543 11.00000 -1.50000 AFIX 0 C12 1 0.524775 0.840090 0.069554 11.00000 0.05156 0.03601 = 0.04046 0.00194 0.01154 -0.00475 H12A 2 0.558473 0.916005 0.050103 11.00000 0.05153 H12B 2 0.624988 0.784735 0.087850 11.00000 0.06244 HKLF 4 REM zhangy_1028 in P21/c #14 REM wR2 = 0.1188, GooF = S = 1.062, Restrained GooF = 1.062 for all data REM R1 = 0.0424 for 1711 Fo > 4sig(Fo) and 0.0457 for all 1899 data REM 144 parameters refined using 0 restraints END WGHT 0.0590 0.2960 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, y-1/2, -z+1/2 HTAB O1 O2_$1 EQIV $2 x, -y+3/2, z+1/2 HTAB O2 O1_$2 REM Highest difference peak 0.228, deepest hole -0.163, 1-sigma level 0.033 Q1 1 0.2862 0.7001 0.1647 11.00000 0.05 0.23 Q2 1 0.3155 0.7597 0.0951 11.00000 0.05 0.20 Q3 1 0.1423 0.6906 0.1938 11.00000 0.05 0.19 Q4 1 0.2847 0.6407 0.2374 11.00000 0.05 0.18 Q5 1 0.2870 0.7425 0.2471 11.00000 0.05 0.17 Q6 1 0.1854 0.6850 0.0748 11.00000 0.05 0.15 Q7 1 -0.0186 0.6430 0.1820 11.00000 0.05 0.14 Q8 1 0.4548 0.9157 0.3887 11.00000 0.05 0.14 Q9 1 0.1956 0.9586 -0.0036 11.00000 0.05 0.14 Q10 1 0.0421 0.8593 0.0368 11.00000 0.05 0.13 Q11 1 0.4058 0.8199 0.0428 11.00000 0.05 0.13 Q12 1 0.2649 0.8460 0.0567 11.00000 0.05 0.12 Q13 1 0.0326 0.6624 0.1083 11.00000 0.05 0.12 Q14 1 0.2137 0.5415 0.2499 11.00000 0.05 0.11 Q15 1 0.2039 0.9770 0.1069 11.00000 0.05 0.11 Q16 1 0.2592 0.6219 0.3411 11.00000 0.05 0.11 Q17 1 0.1157 0.5618 0.0724 11.00000 0.05 0.10 Q18 1 0.2777 0.9959 0.1084 11.00000 0.05 0.10 Q19 1 0.2623 0.7577 0.3875 11.00000 0.05 0.10 Q20 1 0.0295 0.6758 -0.0380 11.00000 0.05 0.10 ; _shelx_res_checksum 18082 _olex2_date_sample_data_collection 2019-10-28 _olex2_submission_special_instructions 'No special instructions were received' ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_zhangye_0917 _database_code_depnum_ccdc_archive 'CCDC 1962276' loop_ _audit_author_name _audit_author_address 'YE ZHANG' ;LANZHOU UNIVERSITY China ; _audit_update_record ; 2019-10-29 deposited with the CCDC. 2020-03-11 downloaded from the CCDC. ; _audit_creation_date 2019-09-18 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _shelx_SHELXL_version_number 2018/3 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C15 H20 O3' _chemical_formula_sum 'C15 H20 O3' _chemical_formula_weight 248.31 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2165(3) _cell_length_b 8.3504(3) _cell_length_c 11.3170(4) _cell_angle_alpha 82.649(3) _cell_angle_beta 76.258(3) _cell_angle_gamma 68.964(4) _cell_volume 617.61(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 6955 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 69.5970 _cell_measurement_theta_min 6.7060 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _exptl_absorpt_coefficient_mu 0.736 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.68488 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_F_000 268 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_unetI/netI 0.0160 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 11512 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 66.587 _diffrn_reflns_theta_max 66.587 _diffrn_reflns_theta_min 4.026 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 41.00 68.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 57.0000 120.0000 27 #__ type_ start__ end____ width___ exp.time_ 2 omega -21.00 12.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 57.0000 120.0000 33 #__ type_ start__ end____ width___ exp.time_ 3 omega -18.00 21.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 38.0000 30.0000 39 #__ type_ start__ end____ width___ exp.time_ 4 omega -38.00 -3.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 125.0000 120.0000 35 #__ type_ start__ end____ width___ exp.time_ 5 omega -80.00 -36.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 178.0000 -180.0000 44 #__ type_ start__ end____ width___ exp.time_ 6 omega 28.00 61.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 38.0000 30.0000 33 #__ type_ start__ end____ width___ exp.time_ 7 omega -55.00 -21.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 20.0000 160.0000 174.6694 34 #__ type_ start__ end____ width___ exp.time_ 8 omega -8.00 17.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.0000 100.0000 -137.2139 25 #__ type_ start__ end____ width___ exp.time_ 9 omega 6.00 36.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.0000 85.0000 33.6144 30 #__ type_ start__ end____ width___ exp.time_ 10 omega -2.00 23.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 40.0000 96.0000 69.8149 25 #__ type_ start__ end____ width___ exp.time_ 11 omega 3.00 28.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 40.0000 87.0000 -94.0549 25 #__ type_ start__ end____ width___ exp.time_ 12 omega 5.00 30.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 44.0000 90.0000 -58.2564 25 #__ type_ start__ end____ width___ exp.time_ 13 omega 15.00 40.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 48.0000 80.0000 56.7675 25 #__ type_ start__ end____ width___ exp.time_ 14 omega 14.00 39.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 48.0000 82.0000 -145.9687 25 #__ type_ start__ end____ width___ exp.time_ 15 omega 19.00 45.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 52.0000 82.0000 -39.2305 26 #__ type_ start__ end____ width___ exp.time_ 16 omega 20.00 46.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 52.0000 78.0000 109.6461 26 #__ type_ start__ end____ width___ exp.time_ 17 omega 32.00 109.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -125.0000 0.0000 77 #__ type_ start__ end____ width___ exp.time_ 18 omega 30.00 66.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 56.0000 66.0000 -114.5049 36 #__ type_ start__ end____ width___ exp.time_ 19 omega 39.00 126.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 60.0000 57.0000 58.8289 87 #__ type_ start__ end____ width___ exp.time_ 20 omega 41.00 67.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 60.0000 56.0000 -132.7581 26 #__ type_ start__ end____ width___ exp.time_ 21 omega 85.00 111.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 60.0000 56.0000 -132.7581 26 #__ type_ start__ end____ width___ exp.time_ 22 omega 37.00 134.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 64.0000 74.0000 -105.4160 97 #__ type_ start__ end____ width___ exp.time_ 23 omega 39.00 101.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 68.0000 73.0000 -6.2651 62 #__ type_ start__ end____ width___ exp.time_ 24 omega 112.00 138.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 68.0000 70.0000 133.3571 26 #__ type_ start__ end____ width___ exp.time_ 25 omega 41.00 79.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 68.0000 70.0000 133.3571 38 #__ type_ start__ end____ width___ exp.time_ 26 omega 90.00 147.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 76.0000 76.0000 -43.2593 57 #__ type_ start__ end____ width___ exp.time_ 27 omega 106.00 145.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 76.0000 57.0000 115.9246 39 #__ type_ start__ end____ width___ exp.time_ 28 omega 55.00 82.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 76.0000 57.0000 115.9246 27 #__ type_ start__ end____ width___ exp.time_ 29 omega 45.00 71.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 76.0000 76.0000 -43.2593 26 #__ type_ start__ end____ width___ exp.time_ 30 omega 121.00 151.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 84.0000 53.0000 66.8398 30 #__ type_ start__ end____ width___ exp.time_ 31 omega 84.00 111.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 84.0000 53.0000 66.8398 27 #__ type_ start__ end____ width___ exp.time_ 32 omega 126.00 158.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 88.0000 50.0000 -161.5837 32 #__ type_ start__ end____ width___ exp.time_ 33 omega 125.00 157.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 88.0000 55.0000 160.2983 32 #__ type_ start__ end____ width___ exp.time_ 34 omega 66.00 94.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 88.0000 50.0000 -161.5837 28 #__ type_ start__ end____ width___ exp.time_ 35 omega 66.00 93.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 88.0000 55.0000 160.2983 27 #__ type_ start__ end____ width___ exp.time_ 36 omega 123.00 157.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 88.0000 71.0000 -27.8578 34 #__ type_ start__ end____ width___ exp.time_ 37 omega 60.00 87.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 88.0000 71.0000 -27.8578 27 #__ type_ start__ end____ width___ exp.time_ 38 omega 63.00 162.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 92.0000 74.0000 37.3235 99 #__ type_ start__ end____ width___ exp.time_ 39 omega 139.00 170.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 68.0000 -31.4462 31 #__ type_ start__ end____ width___ exp.time_ 40 omega 73.00 99.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 68.0000 -31.4462 26 #__ type_ start__ end____ width___ exp.time_ 41 omega 116.00 173.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 104.0000 53.0000 -130.2669 57 #__ type_ start__ end____ width___ exp.time_ 42 omega 83.00 110.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 104.0000 53.0000 -130.2669 27 #__ type_ start__ end____ width___ exp.time_ 43 omega 114.00 140.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 44 omega 76.00 101.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 -150.0000 25 #__ type_ start__ end____ width___ exp.time_ 45 omega 78.00 164.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 0.0000 86 #__ type_ start__ end____ width___ exp.time_ 46 omega 118.00 143.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -91.0000 -90.0000 25 #__ type_ start__ end____ width___ exp.time_ 47 omega 76.00 144.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 -30.0000 68 #__ type_ start__ end____ width___ exp.time_ 48 omega 77.00 178.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 90.0000 101 #__ type_ start__ end____ width___ exp.time_ 49 omega 76.00 177.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 -180.0000 101 #__ type_ start__ end____ width___ exp.time_ 50 omega 76.00 177.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 120.0000 101 #__ type_ start__ end____ width___ exp.time_ 51 omega 130.00 177.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 -120.0000 47 #__ type_ start__ end____ width___ exp.time_ 52 omega 77.00 102.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 -120.0000 25 #__ type_ start__ end____ width___ exp.time_ 53 omega 42.00 109.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 -150.0000 67 #__ type_ start__ end____ width___ exp.time_ 54 omega 35.00 91.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -91.0000 -90.0000 56 #__ type_ start__ end____ width___ exp.time_ 55 omega 108.00 134.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 60.0000 26 #__ type_ start__ end____ width___ exp.time_ 56 omega 80.00 105.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 60.0000 25 #__ type_ start__ end____ width___ exp.time_ 57 omega 144.00 177.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 38.0000 30.0000 33 #__ type_ start__ end____ width___ exp.time_ 58 omega 134.00 160.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 63.0000 -90.0000 26 #__ type_ start__ end____ width___ exp.time_ 59 omega 84.00 114.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 63.0000 -90.0000 30 #__ type_ start__ end____ width___ exp.time_ 60 omega 42.00 103.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 120.0000 61 #__ type_ start__ end____ width___ exp.time_ 61 omega 107.00 132.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -63.0000 -180.0000 25 #__ type_ start__ end____ width___ exp.time_ 62 omega 76.00 149.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 150.0000 73 #__ type_ start__ end____ width___ exp.time_ 63 omega 86.00 111.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 63.0000 0.0000 25 #__ type_ start__ end____ width___ exp.time_ 64 omega 43.00 80.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -63.0000 -180.0000 37 #__ type_ start__ end____ width___ exp.time_ 65 omega 84.00 114.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 63.0000 -120.0000 30 #__ type_ start__ end____ width___ exp.time_ 66 omega 135.00 171.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 111.0000 -90.0000 36 #__ type_ start__ end____ width___ exp.time_ 67 omega 153.00 178.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 150.0000 25 #__ type_ start__ end____ width___ exp.time_ 68 omega 85.00 139.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 63.0000 60.0000 54 #__ type_ start__ end____ width___ exp.time_ 69 omega 143.00 172.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 63.0000 60.0000 29 #__ type_ start__ end____ width___ exp.time_ 70 omega 86.00 176.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 50.0000 -60.0000 90 #__ type_ start__ end____ width___ exp.time_ 71 omega 62.00 114.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 0.0000 52 #__ type_ start__ end____ width___ exp.time_ 72 omega -69.00 22.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -57.0000 -30.0000 91 #__ type_ start__ end____ width___ exp.time_ 73 omega -22.00 17.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 24.0000 104.0000 -16.5684 39 #__ type_ start__ end____ width___ exp.time_ 74 omega -43.00 -16.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 32.0000 153.0000 -65.6635 27 #__ type_ start__ end____ width___ exp.time_ 75 omega 15.00 46.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 48.0000 80.0000 56.7675 31 #__ type_ start__ end____ width___ exp.time_ 76 omega 14.00 45.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 48.0000 82.0000 -145.9687 31 #__ type_ start__ end____ width___ exp.time_ 77 omega 19.00 46.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 52.0000 80.0000 121.4124 27 #__ type_ start__ end____ width___ exp.time_ 78 omega 18.00 45.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 52.0000 82.0000 -39.2305 27 #__ type_ start__ end____ width___ exp.time_ 79 omega -20.00 128.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 0.0000 0.0000 148 #__ type_ start__ end____ width___ exp.time_ 80 omega -20.00 128.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 0.0000 -60.0000 148 #__ type_ start__ end____ width___ exp.time_ 81 omega 1.00 98.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -99.0000 30.0000 97 #__ type_ start__ end____ width___ exp.time_ 82 omega -20.00 128.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 0.0000 -90.0000 148 #__ type_ start__ end____ width___ exp.time_ 83 omega -20.00 128.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 0.0000 -30.0000 148 #__ type_ start__ end____ width___ exp.time_ 84 omega -20.00 128.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 0.0000 -120.0000 148 #__ type_ start__ end____ width___ exp.time_ 85 omega -20.00 128.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 0.0000 -180.0000 148 #__ type_ start__ end____ width___ exp.time_ 86 omega -15.00 76.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -57.0000 -180.0000 91 #__ type_ start__ end____ width___ exp.time_ 87 omega -20.00 105.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 0.0000 -150.0000 125 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.2013737000 _diffrn_orient_matrix_UB_12 -0.0344099000 _diffrn_orient_matrix_UB_13 0.0477476000 _diffrn_orient_matrix_UB_21 0.0260389000 _diffrn_orient_matrix_UB_22 -0.0786506000 _diffrn_orient_matrix_UB_23 -0.1213844000 _diffrn_orient_matrix_UB_31 0.1158724000 _diffrn_orient_matrix_UB_32 -0.1782891000 _diffrn_orient_matrix_UB_33 0.0516610000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_source 'SuperNova (Cu) X-ray Source' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2021 _reflns_number_total 2182 _reflns_odcompleteness_completeness 99.59 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.284 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.043 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 164 _refine_ls_number_reflns 2182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0447 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+0.2315P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1181 _refine_ls_wR_factor_ref 0.1208 _refine_special_details ? _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All O(H) groups 2.a Ternary CH refined with riding coordinates: C9(H9), C13(H13), C14(H14) 2.b Secondary CH2 refined with riding coordinates: C5(H5A,H5B), C6(H6A,H6B), C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B) 2.c Idealised tetrahedral OH refined as rotating group: O3(H3) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary ? loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.12336(19) 0.09934(16) 0.39163(12) 0.0462(3) Uani 1 1 d . . . . . O2 O -0.2227(2) 0.46409(17) 0.04267(12) 0.0520(4) Uani 1 1 d . . . . . O3 O -0.4863(2) 0.21825(18) 0.00633(12) 0.0537(4) Uani 1 1 d . . . . . H3 H -0.576548 0.310317 -0.001085 0.081 Uiso 1 1 calc GR . . . . C4 C -0.1926(2) -0.02424(18) 0.24505(13) 0.0266(3) Uani 1 1 d . . . . . C5 C -0.0730(2) 0.2363(2) 0.17480(14) 0.0323(4) Uani 1 1 d . . . . . H5A H -0.001524 0.300169 0.200252 0.039 Uiso 1 1 calc R . . . . H5B H 0.020393 0.162774 0.110786 0.039 Uiso 1 1 calc R . . . . C6 C -0.2827(2) 0.0240(2) 0.13015(14) 0.0329(4) Uani 1 1 d . . . . . H6A H -0.176713 0.035694 0.062164 0.039 Uiso 1 1 calc R . . . . H6B H -0.318901 -0.071368 0.114613 0.039 Uiso 1 1 calc R . . . . C7 C -0.1388(2) 0.12307(18) 0.28415(13) 0.0273(3) Uani 1 1 d . . . . . C8 C -0.2501(2) 0.3609(2) 0.12452(14) 0.0335(4) Uani 1 1 d . . . . . C9 C -0.4544(2) 0.3467(2) 0.17976(15) 0.0344(4) Uani 1 1 d . . . . . H9 H -0.557619 0.448708 0.152735 0.041 Uiso 1 1 calc R . . . . C10 C 0.0505(2) 0.0296(2) 0.33681(14) 0.0337(4) Uani 1 1 d . . . . . C11 C -0.3067(2) 0.2454(2) 0.37420(14) 0.0336(4) Uani 1 1 d . . . . . H11A H -0.256320 0.328334 0.396093 0.040 Uiso 1 1 calc R . . . . H11B H -0.343687 0.180516 0.447790 0.040 Uiso 1 1 calc R . . . . C12 C -0.3235(2) -0.0999(2) 0.34869(14) 0.0335(4) Uani 1 1 d . . . . . H12A H -0.296188 -0.090721 0.426978 0.040 Uiso 1 1 calc R . . . . H12B H -0.466724 -0.040321 0.350229 0.040 Uiso 1 1 calc R . . . . C13 C -0.4675(2) 0.1865(2) 0.13049(15) 0.0358(4) Uani 1 1 d . . . . . H13 H -0.587553 0.162553 0.178768 0.043 Uiso 1 1 calc R . . . . C14 C 0.0115(2) -0.1779(2) 0.22225(14) 0.0332(4) Uani 1 1 d . . . . . H14 H 0.084024 -0.171708 0.137731 0.040 Uiso 1 1 calc R . . . . C15 C -0.4955(2) 0.3407(2) 0.32006(15) 0.0382(4) Uani 1 1 d . . . . . H15A H -0.553085 0.457483 0.346940 0.046 Uiso 1 1 calc R . . . . H15B H -0.595783 0.285411 0.352014 0.046 Uiso 1 1 calc R . . . . C16 C -0.0461(3) -0.3400(2) 0.2466(2) 0.0515(5) Uani 1 1 d . . . . . H16A H -0.037583 -0.386621 0.170442 0.062 Uiso 1 1 calc R . . . . H16B H 0.044673 -0.426735 0.291938 0.062 Uiso 1 1 calc R . . . . C17 C -0.2627(3) -0.2876(2) 0.3201(2) 0.0555(5) Uani 1 1 d . . . . . H17A H -0.270171 -0.358391 0.394878 0.067 Uiso 1 1 calc R . . . . H17B H -0.352550 -0.301067 0.273602 0.067 Uiso 1 1 calc R . . . . C18 C 0.1322(3) -0.1561(2) 0.3089(2) 0.0524(5) Uani 1 1 d . . . . . H18A H 0.116079 -0.226719 0.383037 0.063 Uiso 1 1 calc R . . . . H18B H 0.275266 -0.189822 0.271106 0.063 Uiso 1 1 calc R . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0479(7) 0.0498(7) 0.0564(8) 0.0008(6) -0.0319(6) -0.0225(6) O2 0.0557(8) 0.0509(8) 0.0547(8) 0.0221(6) -0.0235(6) -0.0251(6) O3 0.0693(9) 0.0522(8) 0.0494(8) 0.0048(6) -0.0410(7) -0.0165(7) C4 0.0267(7) 0.0257(8) 0.0307(7) -0.0021(6) -0.0107(6) -0.0095(6) C5 0.0321(8) 0.0315(8) 0.0387(8) 0.0015(6) -0.0124(6) -0.0150(7) C6 0.0384(8) 0.0343(8) 0.0335(8) -0.0015(6) -0.0154(7) -0.0164(7) C7 0.0284(7) 0.0266(7) 0.0317(7) -0.0008(6) -0.0132(6) -0.0108(6) C8 0.0421(9) 0.0299(8) 0.0348(8) 0.0013(6) -0.0168(7) -0.0149(7) C9 0.0323(8) 0.0310(8) 0.0407(9) 0.0037(6) -0.0172(7) -0.0075(6) C10 0.0316(8) 0.0370(9) 0.0380(8) 0.0030(7) -0.0160(6) -0.0144(7) C11 0.0388(9) 0.0309(8) 0.0337(8) -0.0049(6) -0.0133(7) -0.0101(7) C12 0.0331(8) 0.0323(8) 0.0378(8) 0.0003(6) -0.0092(6) -0.0138(6) C13 0.0359(8) 0.0412(9) 0.0380(8) 0.0046(7) -0.0208(7) -0.0164(7) C14 0.0314(8) 0.0296(8) 0.0379(8) -0.0042(6) -0.0086(6) -0.0078(6) C15 0.0336(8) 0.0368(9) 0.0409(9) -0.0050(7) -0.0100(7) -0.0053(7) C16 0.0492(10) 0.0308(9) 0.0738(13) -0.0052(8) -0.0130(9) -0.0117(8) C17 0.0568(12) 0.0366(10) 0.0734(14) -0.0029(9) -0.0005(10) -0.0244(9) C18 0.0433(10) 0.0393(10) 0.0777(14) -0.0086(9) -0.0345(9) -0.0021(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C10 1.2114(19) . ? O2 C8 1.213(2) . ? O3 H3 0.8200 . ? O3 C13 1.4255(19) . ? C4 C6 1.5348(19) . ? C4 C7 1.5568(18) . ? C4 C12 1.543(2) . ? C4 C14 1.558(2) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5 C7 1.547(2) . ? C5 C8 1.510(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 C13 1.523(2) . ? C7 C10 1.5273(19) . ? C7 C11 1.530(2) . ? C8 C9 1.499(2) . ? C9 H9 0.9800 . ? C9 C13 1.554(2) . ? C9 C15 1.542(2) . ? C10 C18 1.494(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 C15 1.536(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 C17 1.523(2) . ? C13 H13 0.9800 . ? C14 H14 0.9800 . ? C14 C16 1.529(2) . ? C14 C18 1.523(2) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C16 C17 1.520(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O3 H3 109.5 . . ? C6 C4 C7 112.99(12) . . ? C6 C4 C12 111.77(12) . . ? C6 C4 C14 110.59(12) . . ? C7 C4 C14 105.09(11) . . ? C12 C4 C7 113.90(12) . . ? C12 C4 C14 101.65(11) . . ? H5A C5 H5B 107.8 . . ? C7 C5 H5A 109.0 . . ? C7 C5 H5B 109.0 . . ? C8 C5 H5A 109.0 . . ? C8 C5 H5B 109.0 . . ? C8 C5 C7 112.75(12) . . ? C4 C6 H6A 107.9 . . ? C4 C6 H6B 107.9 . . ? H6A C6 H6B 107.2 . . ? C13 C6 C4 117.67(12) . . ? C13 C6 H6A 107.9 . . ? C13 C6 H6B 107.9 . . ? C5 C7 C4 112.85(12) . . ? C10 C7 C4 104.03(11) . . ? C10 C7 C5 105.60(11) . . ? C10 C7 C11 111.85(12) . . ? C11 C7 C4 115.58(12) . . ? C11 C7 C5 106.57(12) . . ? O2 C8 C5 120.08(15) . . ? O2 C8 C9 123.42(15) . . ? C9 C8 C5 116.49(13) . . ? C8 C9 H9 108.1 . . ? C8 C9 C13 108.65(13) . . ? C8 C9 C15 111.48(13) . . ? C13 C9 H9 108.1 . . ? C15 C9 H9 108.1 . . ? C15 C9 C13 112.34(13) . . ? O1 C10 C7 123.81(15) . . ? O1 C10 C18 125.77(15) . . ? C18 C10 C7 110.42(13) . . ? C7 C11 H11A 109.3 . . ? C7 C11 H11B 109.3 . . ? C7 C11 C15 111.58(12) . . ? H11A C11 H11B 108.0 . . ? C15 C11 H11A 109.3 . . ? C15 C11 H11B 109.3 . . ? C4 C12 H12A 110.7 . . ? C4 C12 H12B 110.7 . . ? H12A C12 H12B 108.8 . . ? C17 C12 C4 105.16(13) . . ? C17 C12 H12A 110.7 . . ? C17 C12 H12B 110.7 . . ? O3 C13 C6 104.49(13) . . ? O3 C13 C9 110.30(13) . . ? O3 C13 H13 108.8 . . ? C6 C13 C9 115.44(12) . . ? C6 C13 H13 108.8 . . ? C9 C13 H13 108.8 . . ? C4 C14 H14 110.2 . . ? C16 C14 C4 105.86(12) . . ? C16 C14 H14 110.2 . . ? C18 C14 C4 104.99(12) . . ? C18 C14 H14 110.2 . . ? C18 C14 C16 115.22(15) . . ? C9 C15 H15A 108.7 . . ? C9 C15 H15B 108.7 . . ? C11 C15 C9 114.28(13) . . ? C11 C15 H15A 108.7 . . ? C11 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C14 C16 H16A 110.4 . . ? C14 C16 H16B 110.4 . . ? H16A C16 H16B 108.6 . . ? C17 C16 C14 106.67(14) . . ? C17 C16 H16A 110.4 . . ? C17 C16 H16B 110.4 . . ? C12 C17 H17A 110.4 . . ? C12 C17 H17B 110.4 . . ? C16 C17 C12 106.86(14) . . ? C16 C17 H17A 110.4 . . ? C16 C17 H17B 110.4 . . ? H17A C17 H17B 108.6 . . ? C10 C18 C14 106.72(13) . . ? C10 C18 H18A 110.4 . . ? C10 C18 H18B 110.4 . . ? C14 C18 H18A 110.4 . . ? C14 C18 H18B 110.4 . . ? H18A C18 H18B 108.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C10 C18 C14 -171.20(16) . . . . ? O2 C8 C9 C13 103.78(18) . . . . ? O2 C8 C9 C15 -131.89(17) . . . . ? C4 C6 C13 O3 167.07(13) . . . . ? C4 C6 C13 C9 45.75(19) . . . . ? C4 C7 C10 O1 -169.97(15) . . . . ? C4 C7 C10 C18 11.04(17) . . . . ? C4 C7 C11 C15 -61.98(17) . . . . ? C4 C12 C17 C16 26.7(2) . . . . ? C4 C14 C16 C17 -18.0(2) . . . . ? C4 C14 C18 C10 -23.38(19) . . . . ? C5 C7 C10 O1 70.99(19) . . . . ? C5 C7 C10 C18 -108.00(16) . . . . ? C5 C7 C11 C15 64.30(15) . . . . ? C5 C8 C9 C13 -75.30(16) . . . . ? C5 C8 C9 C15 49.03(19) . . . . ? C6 C4 C7 C5 -31.73(17) . . . . ? C6 C4 C7 C10 -145.70(13) . . . . ? C6 C4 C7 C11 91.28(15) . . . . ? C6 C4 C12 C17 81.28(16) . . . . ? C6 C4 C14 C16 -85.29(16) . . . . ? C6 C4 C14 C18 152.39(14) . . . . ? C7 C4 C6 C13 -54.58(17) . . . . ? C7 C4 C12 C17 -149.14(14) . . . . ? C7 C4 C14 C16 152.47(13) . . . . ? C7 C4 C14 C18 30.15(16) . . . . ? C7 C5 C8 O2 176.18(14) . . . . ? C7 C5 C8 C9 -4.71(19) . . . . ? C7 C10 C18 C14 7.8(2) . . . . ? C7 C11 C15 C9 -20.89(19) . . . . ? C8 C5 C7 C4 76.76(16) . . . . ? C8 C5 C7 C10 -170.23(12) . . . . ? C8 C5 C7 C11 -51.14(16) . . . . ? C8 C9 C13 O3 -72.61(16) . . . . ? C8 C9 C13 C6 45.52(18) . . . . ? C8 C9 C15 C11 -35.02(19) . . . . ? C10 C7 C11 C15 179.24(12) . . . . ? C11 C7 C10 O1 -44.5(2) . . . . ? C11 C7 C10 C18 136.47(15) . . . . ? C12 C4 C6 C13 75.46(16) . . . . ? C12 C4 C7 C5 -160.69(12) . . . . ? C12 C4 C7 C10 85.35(14) . . . . ? C12 C4 C7 C11 -37.67(17) . . . . ? C12 C4 C14 C16 33.52(15) . . . . ? C12 C4 C14 C18 -88.80(15) . . . . ? C13 C9 C15 C11 87.21(16) . . . . ? C14 C4 C6 C13 -172.06(12) . . . . ? C14 C4 C7 C5 88.93(14) . . . . ? C14 C4 C7 C10 -25.03(14) . . . . ? C14 C4 C7 C11 -148.05(12) . . . . ? C14 C4 C12 C17 -36.68(16) . . . . ? C14 C16 C17 C12 -5.2(2) . . . . ? C15 C9 C13 O3 163.57(13) . . . . ? C15 C9 C13 C6 -78.30(17) . . . . ? C16 C14 C18 C10 -139.42(16) . . . . ? C18 C14 C16 C17 97.57(19) . . . . ? _shelx_res_file ; TITL zhangye_0917 in P-1 #2 zhangye_0917.res created by SHELXL-2018/3 at 15:08:32 on 18-Sep-2019 REM reset to P-1 #2 CELL 1.54184 7.216476 8.350446 11.316957 82.6493 76.2579 68.9639 ZERR 2 0.000282 0.00031 0.000445 0.0031 0.0034 0.0035 LATT 1 SFAC C H O UNIT 30 40 6 L.S. 10 PLAN 20 BOND $h htab conf fmap 2 acta SHEL 999 0.84 REM REM REM WGHT 0.061600 0.231500 FVAR 20.77363 O1 3 0.123355 0.099339 0.391632 11.00000 0.04790 0.04976 = 0.05638 0.00079 -0.03191 -0.02252 O2 3 -0.222671 0.464094 0.042669 11.00000 0.05566 0.05092 = 0.05465 0.02209 -0.02352 -0.02508 O3 3 -0.486280 0.218247 0.006331 11.00000 0.06931 0.05216 = 0.04942 0.00483 -0.04103 -0.01646 AFIX 147 H3 2 -0.576548 0.310317 -0.001085 11.00000 -1.50000 AFIX 0 C4 1 -0.192555 -0.024240 0.245054 11.00000 0.02673 0.02573 = 0.03069 -0.00215 -0.01066 -0.00951 C5 1 -0.073012 0.236307 0.174801 11.00000 0.03207 0.03149 = 0.03866 0.00150 -0.01239 -0.01496 AFIX 23 H5A 2 -0.001524 0.300169 0.200252 11.00000 -1.20000 H5B 2 0.020393 0.162774 0.110786 11.00000 -1.20000 AFIX 0 C6 1 -0.282657 0.024010 0.130151 11.00000 0.03842 0.03425 = 0.03349 -0.00146 -0.01536 -0.01638 AFIX 23 H6A 2 -0.176713 0.035694 0.062164 11.00000 -1.20000 H6B 2 -0.318901 -0.071368 0.114613 11.00000 -1.20000 AFIX 0 C7 1 -0.138751 0.123071 0.284151 11.00000 0.02837 0.02662 = 0.03167 -0.00076 -0.01325 -0.01079 C8 1 -0.250119 0.360944 0.124524 11.00000 0.04208 0.02986 = 0.03482 0.00127 -0.01677 -0.01486 C9 1 -0.454381 0.346675 0.179761 11.00000 0.03233 0.03105 = 0.04070 0.00365 -0.01725 -0.00748 AFIX 13 H9 2 -0.557619 0.448708 0.152735 11.00000 -1.20000 AFIX 0 C10 1 0.050533 0.029587 0.336814 11.00000 0.03158 0.03705 = 0.03804 0.00302 -0.01600 -0.01439 C11 1 -0.306689 0.245372 0.374201 11.00000 0.03877 0.03089 = 0.03367 -0.00487 -0.01331 -0.01011 AFIX 23 H11A 2 -0.256320 0.328334 0.396093 11.00000 -1.20000 H11B 2 -0.343687 0.180516 0.447790 11.00000 -1.20000 AFIX 0 C12 1 -0.323485 -0.099949 0.348695 11.00000 0.03306 0.03229 = 0.03778 0.00027 -0.00917 -0.01377 AFIX 23 H12A 2 -0.296188 -0.090721 0.426978 11.00000 -1.20000 H12B 2 -0.466724 -0.040321 0.350229 11.00000 -1.20000 AFIX 0 C13 1 -0.467520 0.186501 0.130487 11.00000 0.03593 0.04123 = 0.03803 0.00459 -0.02075 -0.01639 AFIX 13 H13 2 -0.587553 0.162553 0.178768 11.00000 -1.20000 AFIX 0 C14 1 0.011483 -0.177862 0.222250 11.00000 0.03141 0.02959 = 0.03788 -0.00416 -0.00861 -0.00783 AFIX 13 H14 2 0.084024 -0.171708 0.137731 11.00000 -1.20000 AFIX 0 C15 1 -0.495477 0.340715 0.320062 11.00000 0.03355 0.03681 = 0.04087 -0.00498 -0.00999 -0.00533 AFIX 23 H15A 2 -0.553085 0.457483 0.346940 11.00000 -1.20000 H15B 2 -0.595783 0.285411 0.352014 11.00000 -1.20000 AFIX 0 C16 1 -0.046112 -0.340047 0.246583 11.00000 0.04919 0.03080 = 0.07378 -0.00517 -0.01299 -0.01172 AFIX 23 H16A 2 -0.037583 -0.386621 0.170442 11.00000 -1.20000 H16B 2 0.044673 -0.426735 0.291938 11.00000 -1.20000 AFIX 0 C17 1 -0.262653 -0.287599 0.320150 11.00000 0.05676 0.03660 = 0.07337 -0.00288 -0.00053 -0.02437 AFIX 23 H17A 2 -0.270171 -0.358391 0.394878 11.00000 -1.20000 H17B 2 -0.352550 -0.301067 0.273602 11.00000 -1.20000 AFIX 0 C18 1 0.132175 -0.156106 0.308930 11.00000 0.04333 0.03931 = 0.07775 -0.00860 -0.03449 -0.00209 AFIX 23 H18A 2 0.116079 -0.226719 0.383037 11.00000 -1.20000 H18B 2 0.275266 -0.189822 0.271106 11.00000 -1.20000 AFIX 0 HKLF 4 REM zhangye_0917 in P-1 #2 REM wR2 = 0.1208, GooF = S = 1.084, Restrained GooF = 1.084 for all data REM R1 = 0.0447 for 2021 Fo > 4sig(Fo) and 0.0473 for all 2182 data REM 164 parameters refined using 0 restraints END WGHT 0.0608 0.2373 REM Instructions for potential hydrogen bonds EQIV $1 -x-1, -y+1, -z HTAB O3 O2_$1 REM Highest difference peak 0.284, deepest hole -0.252, 1-sigma level 0.043 Q1 1 -0.0310 -0.3333 0.3265 11.00000 0.05 0.28 Q2 1 -0.1682 0.0448 0.2613 11.00000 0.05 0.23 Q3 1 -0.3504 0.3381 0.1540 11.00000 0.05 0.22 Q4 1 -0.0584 0.0810 0.3165 11.00000 0.05 0.22 Q5 1 0.2038 -0.1248 0.2373 11.00000 0.05 0.22 Q6 1 -0.3493 -0.3496 0.3628 11.00000 0.05 0.21 Q7 1 -0.0945 -0.0961 0.2316 11.00000 0.05 0.20 Q8 1 -0.2596 -0.0557 0.2965 11.00000 0.05 0.19 Q9 1 -0.2163 0.1723 0.3241 11.00000 0.05 0.18 Q10 1 0.2506 -0.2278 0.3359 11.00000 0.05 0.18 Q11 1 0.0705 -0.4588 0.2390 11.00000 0.05 0.16 Q12 1 -0.0985 0.1692 0.2243 11.00000 0.05 0.16 Q13 1 0.0280 -0.2179 0.4213 11.00000 0.05 0.16 Q14 1 -0.1750 0.3027 0.1596 11.00000 0.05 0.16 Q15 1 -0.4677 0.3368 0.2386 11.00000 0.05 0.15 Q16 1 -0.4679 0.2764 0.1613 11.00000 0.05 0.15 Q17 1 -0.1850 -0.3039 0.3864 11.00000 0.05 0.15 Q18 1 -0.3807 0.1056 0.1375 11.00000 0.05 0.15 Q19 1 -0.2301 -0.0010 0.1870 11.00000 0.05 0.15 Q20 1 -0.5913 0.1886 0.1997 11.00000 0.05 0.14 ; _shelx_res_checksum 71204 _olex2_date_sample_data_collection 2019-09-17 _olex2_submission_special_instructions 'No special instructions were received' ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_zhangy_1021 _database_code_depnum_ccdc_archive 'CCDC 1962295' loop_ _audit_author_name _audit_author_address 'YE ZHANG' ;LANZHOU UNIVERSITY China ; _audit_update_record ; 2019-10-29 deposited with the CCDC. 2020-03-11 downloaded from the CCDC. ; _audit_creation_date 2019-10-25 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C23 H28 N2 O3 S' _chemical_formula_sum 'C23 H28 N2 O3 S' _chemical_formula_weight 412.53 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 10.3539(2) _cell_length_b 19.9619(4) _cell_length_c 11.8443(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.384(3) _cell_angle_gamma 90.00 _cell_volume 2246.96(9) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3800 _cell_measurement_temperature 295.00(10) _cell_measurement_theta_max 69.7320 _cell_measurement_theta_min 6.5240 _exptl_absorpt_coefficient_mu 1.480 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.27636 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 880 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_unetI/netI 0.0234 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 8053 _diffrn_reflns_theta_full 66.60 _diffrn_reflns_theta_max 66.60 _diffrn_reflns_theta_min 4.63 _diffrn_ambient_temperature 295.00(10) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.976 _diffrn_measured_fraction_theta_max 0.976 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 23.00 58.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 57.0000 -90.0000 35 #__ type_ start__ end____ width___ exp.time_ 2 omega -22.00 4.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 57.0000 -90.0000 26 #__ type_ start__ end____ width___ exp.time_ 3 omega -80.00 -37.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 178.0000 60.0000 43 #__ type_ start__ end____ width___ exp.time_ 4 omega -84.00 -36.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 178.0000 -180.0000 48 #__ type_ start__ end____ width___ exp.time_ 5 omega -14.00 76.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -40.0000 -63.8281 90 #__ type_ start__ end____ width___ exp.time_ 6 omega -1.00 70.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -57.0000 120.0000 71 #__ type_ start__ end____ width___ exp.time_ 7 omega 34.00 61.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 57.0000 90.0000 27 #__ type_ start__ end____ width___ exp.time_ 8 omega 65.00 92.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 120.0000 27 #__ type_ start__ end____ width___ exp.time_ 9 omega 51.00 77.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 -60.0000 26 #__ type_ start__ end____ width___ exp.time_ 10 omega 54.00 93.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 -180.0000 39 #__ type_ start__ end____ width___ exp.time_ 11 omega 50.00 75.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -50.0000 -120.0000 25 #__ type_ start__ end____ width___ exp.time_ 12 omega 77.00 104.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 150.0000 27 #__ type_ start__ end____ width___ exp.time_ 13 omega 36.00 62.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -38.0000 30.0000 26 #__ type_ start__ end____ width___ exp.time_ 14 omega 64.00 89.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -38.0000 30.0000 25 #__ type_ start__ end____ width___ exp.time_ 15 omega 35.00 93.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -38.0000 -90.0000 58 #__ type_ start__ end____ width___ exp.time_ 16 omega 111.00 142.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 178.0000 -30.0000 31 #__ type_ start__ end____ width___ exp.time_ 17 omega 57.00 88.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 178.0000 -30.0000 31 #__ type_ start__ end____ width___ exp.time_ 18 omega 68.00 93.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 0.0000 25 #__ type_ start__ end____ width___ exp.time_ 19 omega 86.00 113.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 63.0000 -180.0000 27 #__ type_ start__ end____ width___ exp.time_ 20 omega 136.00 173.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 63.0000 -180.0000 37 #__ type_ start__ end____ width___ exp.time_ 21 omega 43.00 122.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -63.0000 90.0000 79 #__ type_ start__ end____ width___ exp.time_ 22 omega 50.00 92.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 60.0000 42 #__ type_ start__ end____ width___ exp.time_ 23 omega 135.00 178.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 111.0000 -150.0000 43 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0916420000 _diffrn_orient_matrix_UB_12 -0.0558728000 _diffrn_orient_matrix_UB_13 0.0832763000 _diffrn_orient_matrix_UB_21 0.0471067000 _diffrn_orient_matrix_UB_22 0.0481803000 _diffrn_orient_matrix_UB_23 0.1107394000 _diffrn_orient_matrix_UB_31 -0.1251318000 _diffrn_orient_matrix_UB_32 -0.0227728000 _diffrn_orient_matrix_UB_33 0.0296767000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_source 'SuperNova (Cu) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3394 _reflns_number_total 3876 _reflns_odcompleteness_completeness 97.44 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.234 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.039 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 270 _refine_ls_number_reflns 3876 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0406 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0621P)^2^+0.5554P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1095 _refine_ls_wR_factor_ref 0.1146 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B) 2.b Aromatic/amide H refined with riding coordinates: C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C18(H18), C19(H19), C21(H21), C22(H22) 2.c Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C23(H23A,H23B, H23C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn S1 S 0.57112(5) 0.10037(2) 0.82476(4) 0.04836(16) Uani 1 d . . . O1 O 0.36800(14) -0.07644(6) 0.79151(11) 0.0479(3) Uani 1 d . . . O2 O 0.47148(16) 0.12597(8) 0.87015(15) 0.0723(5) Uani 1 d . . . O3 O 0.63101(18) 0.14438(7) 0.76384(15) 0.0746(5) Uani 1 d . . . N1 N 0.57102(13) 0.00021(6) 0.69099(11) 0.0347(3) Uani 1 d . . . N2 N 0.48263(15) 0.04209(7) 0.72608(13) 0.0386(3) Uani 1 d . . . H2 H 0.427(2) 0.0208(10) 0.753(2) 0.050(6) Uiso 1 d . . . C1 C 0.50770(15) -0.04717(7) 0.61687(13) 0.0302(3) Uani 1 d . . . C2 C 0.59543(16) -0.09708(7) 0.58526(15) 0.0349(3) Uani 1 d . . . H2A H 0.6940 -0.0850 0.6260 0.042 Uiso 1 calc . . R H2B H 0.5705 -0.0966 0.4972 0.042 Uiso 1 calc . . R C3 C 0.57231(16) -0.16808(8) 0.62575(15) 0.0354(3) Uani 1 d . . . C4 C 0.41309(15) -0.18313(7) 0.57339(15) 0.0345(3) Uani 1 d . . . H4A H 0.3996 -0.2257 0.6068 0.041 Uiso 1 calc . . R H4B H 0.3809 -0.1886 0.4851 0.041 Uiso 1 calc . . R C5 C 0.31785(15) -0.13070(7) 0.59822(13) 0.0312(3) Uani 1 d . . . C6 C 0.35227(15) -0.06125(7) 0.55908(13) 0.0308(3) Uani 1 d . . . H6A H 0.3202 -0.0598 0.4702 0.037 Uiso 1 calc . . R H6B H 0.3024 -0.0268 0.5836 0.037 Uiso 1 calc . . R C7 C 0.16013(16) -0.14448(8) 0.52530(16) 0.0399(4) Uani 1 d . . . C8 C 0.06168(19) -0.10347(10) 0.5438(2) 0.0524(5) Uani 1 d . . . H8 H 0.0922 -0.0695 0.6022 0.063 Uiso 1 calc . . R C9 C -0.0816(2) -0.11252(12) 0.4762(2) 0.0682(6) Uani 1 d . . . H9 H -0.1458 -0.0847 0.4901 0.082 Uiso 1 calc . . R C10 C -0.1291(2) -0.16174(14) 0.3899(3) 0.0834(8) Uani 1 d . . . H10 H -0.2249 -0.1670 0.3434 0.100 Uiso 1 calc . . R C11 C -0.0340(2) -0.20298(15) 0.3727(3) 0.0944(10) Uani 1 d . . . H11 H -0.0659 -0.2374 0.3153 0.113 Uiso 1 calc . . R C12 C 0.1101(2) -0.19481(11) 0.4394(2) 0.0698(7) Uani 1 d . . . H12 H 0.1730 -0.2236 0.4257 0.084 Uiso 1 calc . . R C13 C 0.6418(2) -0.21839(9) 0.5697(2) 0.0521(5) Uani 1 d . . . H13A H 0.6008 -0.2143 0.4817 0.078 Uiso 1 calc . . GR H13B H 0.6271 -0.2630 0.5925 0.078 Uiso 1 calc . . GR H13C H 0.7409 -0.2094 0.5998 0.078 Uiso 1 calc . . GR C14 C 0.64064(19) -0.17377(10) 0.76583(17) 0.0502(4) Uani 1 d . . . H14A H 0.7406 -0.1683 0.7934 0.075 Uiso 1 calc . . GR H14B H 0.6205 -0.2170 0.7904 0.075 Uiso 1 calc . . GR H14C H 0.6037 -0.1396 0.8017 0.075 Uiso 1 calc . . GR C15 C 0.33784(16) -0.12828(8) 0.73376(15) 0.0366(3) Uani 1 d . . . C16 C 0.3108(2) -0.19054(10) 0.7922(2) 0.0595(5) Uani 1 d . . . H16A H 0.3756 -0.1925 0.8768 0.089 Uiso 1 calc . . GR H16B H 0.3233 -0.2292 0.7494 0.089 Uiso 1 calc . . GR H16C H 0.2162 -0.1897 0.7878 0.089 Uiso 1 calc . . GR C17 C 0.71036(18) 0.06065(9) 0.94461(15) 0.0429(4) Uani 1 d . . . C18 C 0.68919(18) 0.00048(9) 0.99188(16) 0.0467(4) Uani 1 d . . . H18 H 0.6019 -0.0205 0.9586 0.056 Uiso 1 calc . . R C19 C 0.79864(19) -0.02845(11) 1.08904(17) 0.0530(5) Uani 1 d . . . H19 H 0.7840 -0.0689 1.1209 0.064 Uiso 1 calc . . R C20 C 0.9299(2) 0.00164(12) 1.13999(18) 0.0585(5) Uani 1 d . . . C21 C 0.9484(2) 0.06191(14) 1.0918(2) 0.0723(7) Uani 1 d . . . H21 H 1.0355 0.0831 1.1259 0.087 Uiso 1 calc . . R C22 C 0.8406(2) 0.09176(11) 0.9940(2) 0.0627(5) Uani 1 d . . . H22 H 0.8554 0.1322 0.9619 0.075 Uiso 1 calc . . R C23 C 1.0492(2) -0.03030(16) 1.2460(2) 0.0854(8) Uani 1 d . . . H23A H 1.0422 -0.0183 1.3219 0.128 Uiso 1 calc . . GR H23B H 1.1373 -0.0148 1.2469 0.128 Uiso 1 calc . . GR H23C H 1.0438 -0.0781 1.2366 0.128 Uiso 1 calc . . GR loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0556(3) 0.0282(2) 0.0487(3) -0.00734(16) 0.0073(2) -0.00033(17) O1 0.0629(8) 0.0458(7) 0.0402(6) -0.0051(5) 0.0259(6) -0.0037(6) O2 0.0692(9) 0.0593(9) 0.0733(10) -0.0259(8) 0.0124(8) 0.0213(7) O3 0.0905(11) 0.0392(7) 0.0729(10) 0.0081(7) 0.0099(9) -0.0202(7) N1 0.0345(6) 0.0300(6) 0.0350(7) 0.0010(5) 0.0091(5) -0.0013(5) N2 0.0397(7) 0.0309(7) 0.0395(7) -0.0039(5) 0.0095(6) 0.0005(6) C1 0.0323(7) 0.0269(7) 0.0292(7) 0.0051(5) 0.0097(6) -0.0015(6) C2 0.0326(7) 0.0346(8) 0.0384(8) -0.0005(6) 0.0150(6) -0.0026(6) C3 0.0333(7) 0.0315(8) 0.0425(8) 0.0036(6) 0.0162(7) 0.0048(6) C4 0.0362(8) 0.0266(7) 0.0427(8) -0.0029(6) 0.0179(7) -0.0015(6) C5 0.0302(7) 0.0267(7) 0.0363(8) -0.0001(6) 0.0128(6) -0.0008(6) C6 0.0303(7) 0.0278(7) 0.0297(7) 0.0017(5) 0.0069(6) 0.0009(6) C7 0.0329(8) 0.0377(8) 0.0490(9) -0.0010(7) 0.0161(7) -0.0057(6) C8 0.0372(9) 0.0572(11) 0.0634(12) -0.0047(9) 0.0206(9) -0.0011(8) C9 0.0357(9) 0.0774(14) 0.0933(17) 0.0052(13) 0.0274(11) 0.0024(10) C10 0.0362(10) 0.0932(18) 0.107(2) -0.0121(16) 0.0142(12) -0.0212(11) C11 0.0501(12) 0.0955(19) 0.121(2) -0.0503(18) 0.0156(14) -0.0281(13) C12 0.0444(10) 0.0621(13) 0.0958(17) -0.0349(12) 0.0201(11) -0.0142(9) C13 0.0499(10) 0.0392(9) 0.0764(13) -0.0026(9) 0.0348(10) 0.0067(8) C14 0.0426(9) 0.0552(11) 0.0480(10) 0.0149(8) 0.0128(8) 0.0124(8) C15 0.0372(8) 0.0351(8) 0.0408(8) 0.0033(7) 0.0190(7) 0.0037(6) C16 0.0824(14) 0.0486(11) 0.0606(12) 0.0148(9) 0.0423(11) 0.0033(10) C17 0.0422(9) 0.0434(9) 0.0382(8) -0.0108(7) 0.0106(7) -0.0043(7) C18 0.0387(8) 0.0517(10) 0.0441(9) -0.0039(8) 0.0106(7) -0.0039(7) C19 0.0470(10) 0.0626(12) 0.0460(10) 0.0037(9) 0.0149(8) 0.0033(9) C20 0.0395(9) 0.0873(15) 0.0437(10) -0.0017(10) 0.0111(8) 0.0019(9) C21 0.0429(10) 0.0984(18) 0.0597(13) -0.0047(12) 0.0033(10) -0.0220(11) C22 0.0572(11) 0.0633(13) 0.0574(12) -0.0049(10) 0.0120(10) -0.0210(10) C23 0.0492(12) 0.132(2) 0.0600(14) 0.0141(15) 0.0055(11) 0.0134(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.4335(16) . ? S1 O3 1.4255(16) . ? S1 N2 1.6459(13) . ? S1 C17 1.7601(18) . ? O1 C15 1.211(2) . ? N1 N2 1.4181(19) . ? N1 C1 1.2800(19) . ? N2 H2 0.87(2) . ? C1 C2 1.493(2) . ? C1 C6 1.5043(19) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C2 C3 1.545(2) . ? C3 C4 1.543(2) . ? C3 C13 1.531(2) . ? C3 C14 1.528(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C4 C5 1.544(2) . ? C5 C6 1.548(2) . ? C5 C7 1.539(2) . ? C5 C15 1.536(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.391(2) . ? C7 C12 1.377(3) . ? C8 H8 0.9300 . ? C8 C9 1.390(3) . ? C9 H9 0.9300 . ? C9 C10 1.361(4) . ? C10 H10 0.9300 . ? C10 C11 1.358(4) . ? C11 H11 0.9300 . ? C11 C12 1.394(3) . ? C12 H12 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.502(2) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.379(3) . ? C17 C22 1.386(3) . ? C18 H18 0.9300 . ? C18 C19 1.381(3) . ? C19 H19 0.9300 . ? C19 C20 1.386(3) . ? C20 C21 1.377(3) . ? C20 C23 1.509(3) . ? C21 H21 0.9300 . ? C21 C22 1.385(3) . ? C22 H22 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 N2 103.75(8) . . ? O2 S1 C17 109.83(9) . . ? O3 S1 O2 119.51(11) . . ? O3 S1 N2 107.91(9) . . ? O3 S1 C17 107.72(9) . . ? N2 S1 C17 107.53(7) . . ? C1 N1 N2 114.97(12) . . ? S1 N2 H2 110.6(14) . . ? N1 N2 S1 112.50(10) . . ? N1 N2 H2 114.5(13) . . ? N1 C1 C2 117.92(13) . . ? N1 C1 C6 127.90(14) . . ? C2 C1 C6 114.14(12) . . ? C1 C2 H2A 109.6 . . ? C1 C2 H2B 109.6 . . ? C1 C2 C3 110.47(12) . . ? H2A C2 H2B 108.1 . . ? C3 C2 H2A 109.6 . . ? C3 C2 H2B 109.6 . . ? C4 C3 C2 109.04(12) . . ? C13 C3 C2 108.04(13) . . ? C13 C3 C4 107.98(13) . . ? C14 C3 C2 110.07(14) . . ? C14 C3 C4 112.48(13) . . ? C14 C3 C13 109.11(14) . . ? C3 C4 H4A 108.1 . . ? C3 C4 H4B 108.1 . . ? C3 C4 C5 116.92(12) . . ? H4A C4 H4B 107.3 . . ? C5 C4 H4A 108.1 . . ? C5 C4 H4B 108.1 . . ? C4 C5 C6 108.05(11) . . ? C7 C5 C4 112.80(12) . . ? C7 C5 C6 108.12(12) . . ? C15 C5 C4 112.90(12) . . ? C15 C5 C6 109.48(12) . . ? C15 C5 C7 105.37(12) . . ? C1 C6 C5 111.28(11) . . ? C1 C6 H6A 109.4 . . ? C1 C6 H6B 109.4 . . ? C5 C6 H6A 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C5 119.16(15) . . ? C12 C7 C5 123.32(15) . . ? C12 C7 C8 117.50(17) . . ? C7 C8 H8 119.5 . . ? C9 C8 C7 120.96(19) . . ? C9 C8 H8 119.5 . . ? C8 C9 H9 119.6 . . ? C10 C9 C8 120.7(2) . . ? C10 C9 H9 119.6 . . ? C9 C10 H10 120.6 . . ? C11 C10 C9 118.9(2) . . ? C11 C10 H10 120.6 . . ? C10 C11 H11 119.3 . . ? C10 C11 C12 121.4(2) . . ? C12 C11 H11 119.3 . . ? C7 C12 C11 120.5(2) . . ? C7 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C3 C13 H13A 109.5 . . ? C3 C13 H13B 109.5 . . ? C3 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C3 C14 H14A 109.5 . . ? C3 C14 H14B 109.5 . . ? C3 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O1 C15 C5 120.98(14) . . ? O1 C15 C16 120.01(15) . . ? C16 C15 C5 118.90(14) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 S1 120.57(13) . . ? C18 C17 C22 120.26(18) . . ? C22 C17 S1 119.14(15) . . ? C17 C18 H18 120.2 . . ? C17 C18 C19 119.50(17) . . ? C19 C18 H18 120.2 . . ? C18 C19 H19 119.3 . . ? C18 C19 C20 121.4(2) . . ? C20 C19 H19 119.3 . . ? C19 C20 C23 121.1(2) . . ? C21 C20 C19 118.16(19) . . ? C21 C20 C23 120.8(2) . . ? C20 C21 H21 119.2 . . ? C20 C21 C22 121.60(19) . . ? C22 C21 H21 119.2 . . ? C17 C22 H22 120.4 . . ? C21 C22 C17 119.1(2) . . ? C21 C22 H22 120.4 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S1 C17 C18 C19 -177.53(14) . . . . ? S1 C17 C22 C21 177.22(17) . . . . ? O2 S1 N2 N1 -166.71(11) . . . . ? O2 S1 C17 C18 70.66(16) . . . . ? O2 S1 C17 C22 -107.09(18) . . . . ? O3 S1 N2 N1 65.55(13) . . . . ? O3 S1 C17 C18 -157.67(15) . . . . ? O3 S1 C17 C22 24.58(19) . . . . ? N1 C1 C2 C3 119.02(14) . . . . ? N1 C1 C6 C5 -118.41(16) . . . . ? N2 S1 C17 C18 -41.60(17) . . . . ? N2 S1 C17 C22 140.65(16) . . . . ? N2 N1 C1 C2 -174.34(12) . . . . ? N2 N1 C1 C6 3.2(2) . . . . ? C1 N1 N2 S1 178.14(11) . . . . ? C1 C2 C3 C4 52.19(16) . . . . ? C1 C2 C3 C13 169.31(13) . . . . ? C1 C2 C3 C14 -71.64(16) . . . . ? C2 C1 C6 C5 59.17(16) . . . . ? C2 C3 C4 C5 -51.82(17) . . . . ? C3 C4 C5 C6 51.26(17) . . . . ? C3 C4 C5 C7 170.73(13) . . . . ? C3 C4 C5 C15 -69.95(17) . . . . ? C4 C5 C6 C1 -51.80(15) . . . . ? C4 C5 C7 C8 176.41(15) . . . . ? C4 C5 C7 C12 -5.2(2) . . . . ? C4 C5 C15 O1 124.33(16) . . . . ? C4 C5 C15 C16 -59.36(19) . . . . ? C5 C7 C8 C9 177.39(18) . . . . ? C5 C7 C12 C11 -177.3(2) . . . . ? C6 C1 C2 C3 -58.82(16) . . . . ? C6 C5 C7 C8 -64.17(19) . . . . ? C6 C5 C7 C12 114.2(2) . . . . ? C6 C5 C15 O1 3.9(2) . . . . ? C6 C5 C15 C16 -179.76(14) . . . . ? C7 C5 C6 C1 -174.18(12) . . . . ? C7 C5 C15 O1 -112.13(16) . . . . ? C7 C5 C15 C16 64.18(18) . . . . ? C7 C8 C9 C10 -0.2(4) . . . . ? C8 C7 C12 C11 1.0(4) . . . . ? C8 C9 C10 C11 1.5(4) . . . . ? C9 C10 C11 C12 -1.5(5) . . . . ? C10 C11 C12 C7 0.3(5) . . . . ? C12 C7 C8 C9 -1.1(3) . . . . ? C13 C3 C4 C5 -168.98(14) . . . . ? C14 C3 C4 C5 70.57(17) . . . . ? C15 C5 C6 C1 71.52(15) . . . . ? C15 C5 C7 C8 52.82(19) . . . . ? C15 C5 C7 C12 -128.8(2) . . . . ? C17 S1 N2 N1 -50.39(13) . . . . ? C17 C18 C19 C20 -0.2(3) . . . . ? C18 C17 C22 C21 -0.5(3) . . . . ? C18 C19 C20 C21 0.6(3) . . . . ? C18 C19 C20 C23 -179.9(2) . . . . ? C19 C20 C21 C22 -1.0(4) . . . . ? C20 C21 C22 C17 1.0(4) . . . . ? C22 C17 C18 C19 0.2(3) . . . . ? C23 C20 C21 C22 179.5(2) . . . . ? _olex2_date_sample_data_collection 2019-10-21 _olex2_submission_special_instructions 'No special instructions were received' ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_zhangy_0518 _database_code_depnum_ccdc_archive 'CCDC 1962296' loop_ _audit_author_name _audit_author_address 'YE ZHANG' ;LANZHOU UNIVERSITY China ; _audit_update_record ; 2019-10-29 deposited with the CCDC. 2020-03-11 downloaded from the CCDC. ; _audit_creation_date 2018-05-18 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C22 H30 N2 O4 S' _chemical_formula_sum 'C22 H30 N2 O4 S' _chemical_formula_weight 418.54 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.9610(3) _cell_length_b 17.5295(6) _cell_length_c 13.2899(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.667(3) _cell_angle_gamma 90.00 _cell_volume 2272.62(13) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2956 _cell_measurement_temperature 295.3(2) _cell_measurement_theta_max 69.6190 _cell_measurement_theta_min 5.0230 _exptl_absorpt_coefficient_mu 1.501 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.48170 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.223 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 896 _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_unetI/netI 0.0245 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 7941 _diffrn_reflns_theta_full 66.59 _diffrn_reflns_theta_max 66.59 _diffrn_reflns_theta_min 4.23 _diffrn_ambient_temperature 295.3(2) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.972 _diffrn_measured_fraction_theta_max 0.972 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -29.00 35.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 57.0000 -150.0000 64 #__ type_ start__ end____ width___ exp.time_ 2 omega -79.00 -44.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 178.0000 -120.0000 35 #__ type_ start__ end____ width___ exp.time_ 3 omega -76.00 -34.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 178.0000 -30.0000 42 #__ type_ start__ end____ width___ exp.time_ 4 omega 32.00 119.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 57.0000 -60.0000 87 #__ type_ start__ end____ width___ exp.time_ 5 omega 33.00 121.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 57.0000 -120.0000 88 #__ type_ start__ end____ width___ exp.time_ 6 omega 102.00 132.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 178.0000 90.0000 30 #__ type_ start__ end____ width___ exp.time_ 7 omega 146.00 175.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 111.0000 -150.0000 29 #__ type_ start__ end____ width___ exp.time_ 8 omega 39.00 139.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -77.0000 -120.0000 100 #__ type_ start__ end____ width___ exp.time_ 9 omega 116.00 177.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 25.0000 -60.0000 61 #__ type_ start__ end____ width___ exp.time_ 10 omega 35.00 65.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -38.0000 -30.0000 30 #__ type_ start__ end____ width___ exp.time_ 11 omega 35.00 93.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -38.0000 -120.0000 58 #__ type_ start__ end____ width___ exp.time_ 12 omega 35.00 91.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 30.0000 56 #__ type_ start__ end____ width___ exp.time_ 13 omega 63.00 88.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 -30.0000 25 #__ type_ start__ end____ width___ exp.time_ 14 omega 57.00 94.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 -30.0000 37 #__ type_ start__ end____ width___ exp.time_ 15 omega 64.00 103.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 12.0000 -120.0000 39 #__ type_ start__ end____ width___ exp.time_ 16 omega 115.00 166.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 12.0000 -120.0000 51 #__ type_ start__ end____ width___ exp.time_ 17 omega 44.00 88.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 -180.0000 44 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.1564485000 _diffrn_orient_matrix_UB_12 0.0066793000 _diffrn_orient_matrix_UB_13 0.0105267000 _diffrn_orient_matrix_UB_21 0.0102671000 _diffrn_orient_matrix_UB_22 0.0408583000 _diffrn_orient_matrix_UB_23 0.1039223000 _diffrn_orient_matrix_UB_31 0.0188890000 _diffrn_orient_matrix_UB_32 -0.0774888000 _diffrn_orient_matrix_UB_33 0.0557221000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_source 'SuperNova (Cu) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3232 _reflns_number_total 3890 _reflns_odcompleteness_completeness 96.72 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.856 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.046 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 270 _refine_ls_number_reflns 3890 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0666 _refine_ls_R_factor_gt 0.0565 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0918P)^2^+1.0790P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1590 _refine_ls_wR_factor_ref 0.1700 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C3(H3), C11(H11) 2.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B) 2.c Aromatic/amide H refined with riding coordinates: C4(H4), C17(H17), C18(H18), C20(H20), C21(H21) 2.d Idealised Me refined as rotating group: C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C22(H22A,H22B, H22C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn S1 S 0.19798(6) 0.06550(4) 0.06891(5) 0.0487(2) Uani 1 d . . . O1 O 0.3350(3) 0.38673(14) 0.05356(18) 0.0790(7) Uani 1 d . . . O2 O 0.2883(4) 0.50154(17) -0.0164(3) 0.1106(11) Uani 1 d . . . O3 O 0.2791(2) 0.10408(12) 0.15388(14) 0.0653(6) Uani 1 d . . . O4 O 0.1458(2) -0.00917(11) 0.08445(15) 0.0608(5) Uani 1 d . . . N1 N 0.0876(2) 0.19033(11) -0.00272(15) 0.0463(5) Uani 1 d . . . N2 N 0.0599(2) 0.11582(13) 0.02616(18) 0.0502(5) Uani 1 d . . . H2 H 0.004(3) 0.0937(17) -0.008(2) 0.048(8) Uiso 1 d . . . C1 C 0.0027(3) 0.30572(15) -0.09641(19) 0.0476(6) Uani 1 d . . . C2 C 0.0509(3) 0.30452(16) -0.1993(2) 0.0550(6) Uani 1 d . . . H2A H -0.0099 0.2720 -0.2471 0.066 Uiso 1 calc . . R H2B H 0.0443 0.3557 -0.2277 0.066 Uiso 1 calc . . R C3 C 0.1978(3) 0.27602(18) -0.1895(2) 0.0605(7) Uani 1 d . . . H3 H 0.1995 0.2219 -0.1710 0.073 Uiso 1 calc . . R C4 C 0.2900(3) 0.31830(19) -0.1029(3) 0.0676(8) Uani 1 d . . . H4 H 0.3835 0.3202 -0.1021 0.081 Uiso 1 calc . . R C5 C 0.2434(3) 0.35223(17) -0.0293(2) 0.0599(7) Uani 1 d . . . C6 C 0.0980(3) 0.35525(16) -0.0184(2) 0.0554(6) Uani 1 d . . . H6A H 0.0666 0.4077 -0.0261 0.066 Uiso 1 calc . . R H6B H 0.0925 0.3387 0.0504 0.066 Uiso 1 calc . . R C7 C -0.1469(3) 0.33261(17) -0.1119(2) 0.0604(7) Uani 1 d . . . H7A H -0.1683 0.3488 -0.0472 0.072 Uiso 1 calc . . R H7B H -0.1632 0.3749 -0.1599 0.072 Uiso 1 calc . . R C8 C -0.2337(3) 0.26370(19) -0.1548(3) 0.0684(8) Uani 1 d . . . H8A H -0.2446 0.2610 -0.2289 0.082 Uiso 1 calc . . R H8B H -0.3237 0.2663 -0.1376 0.082 Uiso 1 calc . . R C9 C -0.1529(3) 0.19450(18) -0.1031(2) 0.0622(7) Uani 1 d . . . H9A H -0.1938 0.1750 -0.0479 0.075 Uiso 1 calc . . R H9B H -0.1511 0.1540 -0.1525 0.075 Uiso 1 calc . . R C10 C -0.0103(3) 0.22404(14) -0.06169(18) 0.0455(5) Uani 1 d . . . C11 C 0.2409(4) 0.2827(2) -0.2953(3) 0.0806(10) Uani 1 d . . . H11 H 0.2153 0.3337 -0.3228 0.097 Uiso 1 calc . . R C12 C 0.3871(5) 0.2725(4) -0.2915(4) 0.1240(19) Uani 1 d . . . H12A H 0.4350 0.3185 -0.2671 0.186 Uiso 1 calc . . GR H12B H 0.4018 0.2609 -0.3590 0.186 Uiso 1 calc . . GR H12C H 0.4207 0.2312 -0.2458 0.186 Uiso 1 calc . . GR C13 C 0.1624(5) 0.2244(3) -0.3702(3) 0.1143(18) Uani 1 d . . . H13A H 0.1934 0.1739 -0.3490 0.171 Uiso 1 calc . . GR H13B H 0.1784 0.2341 -0.4379 0.171 Uiso 1 calc . . GR H13C H 0.0662 0.2285 -0.3708 0.171 Uiso 1 calc . . GR C14 C 0.3447(4) 0.4632(2) 0.0535(3) 0.0803(10) Uani 1 d . . . C15 C 0.4332(5) 0.4912(3) 0.1507(3) 0.1085(15) Uani 1 d . . . H15A H 0.3847 0.4866 0.2059 0.163 Uiso 1 calc . . GR H15B H 0.4562 0.5437 0.1427 0.163 Uiso 1 calc . . GR H15C H 0.5156 0.4613 0.1659 0.163 Uiso 1 calc . . GR C16 C 0.2910(3) 0.06110(14) -0.0302(2) 0.0469(6) Uani 1 d . . . C17 C 0.4148(3) 0.09823(18) -0.0197(2) 0.0638(7) Uani 1 d . . . H17 H 0.4501 0.1255 0.0398 0.077 Uiso 1 calc . . R C18 C 0.4854(3) 0.0946(2) -0.0979(3) 0.0724(9) Uani 1 d . . . H18 H 0.5694 0.1194 -0.0901 0.087 Uiso 1 calc . . R C19 C 0.4363(3) 0.05549(18) -0.1878(2) 0.0628(7) Uani 1 d . . . C20 C 0.3121(3) 0.0182(2) -0.1966(2) 0.0701(8) Uani 1 d . . . H20 H 0.2768 -0.0087 -0.2564 0.084 Uiso 1 calc . . R C21 C 0.2395(3) 0.02023(18) -0.1185(2) 0.0632(7) Uani 1 d . . . H21 H 0.1567 -0.0057 -0.1252 0.076 Uiso 1 calc . . R C22 C 0.5145(4) 0.0521(2) -0.2734(3) 0.0889(11) Uani 1 d . . . H22A H 0.5664 0.0056 -0.2683 0.133 Uiso 1 calc . . GR H22B H 0.5757 0.0949 -0.2682 0.133 Uiso 1 calc . . GR H22C H 0.4514 0.0537 -0.3384 0.133 Uiso 1 calc . . GR loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0493(4) 0.0483(4) 0.0433(3) 0.0042(2) -0.0028(3) -0.0037(2) O1 0.0751(15) 0.0830(16) 0.0711(14) -0.0113(12) -0.0036(11) -0.0088(12) O2 0.137(3) 0.0771(18) 0.104(2) -0.0041(16) -0.006(2) -0.0270(17) O3 0.0715(13) 0.0706(13) 0.0448(10) -0.0035(9) -0.0093(9) -0.0082(10) O4 0.0633(12) 0.0534(11) 0.0601(11) 0.0157(8) -0.0010(9) -0.0077(9) N1 0.0479(12) 0.0449(11) 0.0464(11) 0.0020(8) 0.0105(9) -0.0022(9) N2 0.0470(12) 0.0481(12) 0.0530(12) 0.0038(10) 0.0043(10) -0.0044(10) C1 0.0484(14) 0.0490(13) 0.0464(13) 0.0037(10) 0.0114(11) 0.0006(11) C2 0.0612(16) 0.0569(15) 0.0481(14) 0.0043(11) 0.0137(12) -0.0062(12) C3 0.0624(17) 0.0641(17) 0.0605(16) -0.0076(13) 0.0257(14) -0.0102(13) C4 0.0527(16) 0.078(2) 0.075(2) -0.0107(16) 0.0192(14) -0.0077(14) C5 0.0581(16) 0.0585(16) 0.0609(16) -0.0063(13) 0.0071(13) -0.0083(13) C6 0.0667(17) 0.0479(14) 0.0543(14) -0.0026(11) 0.0189(13) -0.0015(12) C7 0.0561(16) 0.0635(17) 0.0630(16) 0.0138(13) 0.0153(13) 0.0124(13) C8 0.0474(15) 0.076(2) 0.078(2) 0.0187(16) 0.0045(14) 0.0044(14) C9 0.0482(15) 0.0630(17) 0.0712(18) 0.0123(14) 0.0027(13) -0.0058(12) C10 0.0443(13) 0.0490(13) 0.0446(12) 0.0016(10) 0.0123(10) 0.0000(10) C11 0.084(2) 0.091(2) 0.078(2) -0.0131(18) 0.0417(19) -0.0189(19) C12 0.084(3) 0.193(6) 0.103(3) 0.000(3) 0.040(3) 0.006(3) C13 0.140(4) 0.134(4) 0.084(3) -0.048(3) 0.059(3) -0.048(3) C14 0.077(2) 0.083(2) 0.079(2) -0.023(2) 0.0125(18) -0.0192(19) C15 0.094(3) 0.135(4) 0.090(3) -0.043(3) 0.004(2) -0.031(3) C16 0.0418(12) 0.0447(13) 0.0493(13) 0.0049(10) -0.0025(10) 0.0021(10) C17 0.0525(16) 0.0665(18) 0.0674(18) -0.0043(14) 0.0002(13) -0.0153(13) C18 0.0489(16) 0.081(2) 0.087(2) 0.0052(18) 0.0125(15) -0.0116(15) C19 0.0590(17) 0.0636(17) 0.0669(18) 0.0139(14) 0.0155(14) 0.0145(13) C20 0.0655(19) 0.082(2) 0.0607(17) -0.0118(15) 0.0082(14) -0.0019(16) C21 0.0513(15) 0.0738(19) 0.0615(16) -0.0109(14) 0.0040(13) -0.0131(14) C22 0.088(3) 0.097(3) 0.091(3) 0.021(2) 0.038(2) 0.020(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O3 1.4202(19) . ? S1 O4 1.4388(19) . ? S1 N2 1.636(2) . ? S1 C16 1.758(3) . ? O1 C5 1.416(3) . ? O1 C14 1.344(5) . ? O2 C14 1.191(5) . ? N1 N2 1.404(3) . ? N1 C10 1.267(3) . ? N2 H2 0.75(3) . ? C1 C2 1.538(3) . ? C1 C6 1.528(4) . ? C1 C7 1.536(4) . ? C1 C10 1.518(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C2 C3 1.526(4) . ? C3 H3 0.9800 . ? C3 C4 1.513(4) . ? C3 C11 1.555(4) . ? C4 H4 0.9300 . ? C4 C5 1.308(4) . ? C5 C6 1.486(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 C8 1.527(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 C9 1.539(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 C10 1.508(4) . ? C11 H11 0.9800 . ? C11 C12 1.458(5) . ? C11 C13 1.527(5) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.492(5) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.377(4) . ? C16 C21 1.382(4) . ? C17 H17 0.9300 . ? C17 C18 1.368(5) . ? C18 H18 0.9300 . ? C18 C19 1.379(5) . ? C19 C20 1.383(5) . ? C19 C22 1.505(5) . ? C20 H20 0.9300 . ? C20 C21 1.380(4) . ? C21 H21 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 O4 118.90(12) . . ? O3 S1 N2 108.84(13) . . ? O3 S1 C16 108.36(13) . . ? O4 S1 N2 103.72(12) . . ? O4 S1 C16 109.15(13) . . ? N2 S1 C16 107.28(11) . . ? C14 O1 C5 117.4(3) . . ? C10 N1 N2 115.7(2) . . ? S1 N2 H2 114(2) . . ? N1 N2 S1 113.47(17) . . ? N1 N2 H2 118(2) . . ? C6 C1 C2 110.4(2) . . ? C6 C1 C7 111.7(2) . . ? C7 C1 C2 110.7(2) . . ? C10 C1 C2 108.6(2) . . ? C10 C1 C6 114.1(2) . . ? C10 C1 C7 101.0(2) . . ? C1 C2 H2A 108.9 . . ? C1 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? C3 C2 C1 113.3(2) . . ? C3 C2 H2A 108.9 . . ? C3 C2 H2B 108.9 . . ? C2 C3 H3 107.8 . . ? C2 C3 C11 109.5(3) . . ? C4 C3 C2 109.2(2) . . ? C4 C3 H3 107.8 . . ? C4 C3 C11 114.5(3) . . ? C11 C3 H3 107.8 . . ? C3 C4 H4 118.7 . . ? C5 C4 C3 122.7(3) . . ? C5 C4 H4 118.7 . . ? O1 C5 C6 113.3(3) . . ? C4 C5 O1 120.4(3) . . ? C4 C5 C6 126.1(3) . . ? C1 C6 H6A 108.9 . . ? C1 C6 H6B 108.9 . . ? C5 C6 C1 113.5(2) . . ? C5 C6 H6A 108.9 . . ? C5 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? C1 C7 H7A 110.6 . . ? C1 C7 H7B 110.6 . . ? H7A C7 H7B 108.8 . . ? C8 C7 C1 105.6(2) . . ? C8 C7 H7A 110.6 . . ? C8 C7 H7B 110.6 . . ? C7 C8 H8A 110.8 . . ? C7 C8 H8B 110.8 . . ? C7 C8 C9 104.5(2) . . ? H8A C8 H8B 108.9 . . ? C9 C8 H8A 110.8 . . ? C9 C8 H8B 110.8 . . ? C8 C9 H9A 110.7 . . ? C8 C9 H9B 110.7 . . ? H9A C9 H9B 108.8 . . ? C10 C9 C8 105.2(2) . . ? C10 C9 H9A 110.7 . . ? C10 C9 H9B 110.7 . . ? N1 C10 C1 121.7(2) . . ? N1 C10 C9 128.0(2) . . ? C9 C10 C1 110.2(2) . . ? C3 C11 H11 107.9 . . ? C12 C11 C3 114.6(4) . . ? C12 C11 H11 107.9 . . ? C12 C11 C13 108.4(4) . . ? C13 C11 C3 109.9(3) . . ? C13 C11 H11 107.9 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O1 C14 C15 110.9(4) . . ? O2 C14 O1 122.7(3) . . ? O2 C14 C15 126.3(4) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 S1 120.1(2) . . ? C17 C16 C21 120.1(3) . . ? C21 C16 S1 119.8(2) . . ? C16 C17 H17 120.3 . . ? C18 C17 C16 119.3(3) . . ? C18 C17 H17 120.3 . . ? C17 C18 H18 118.9 . . ? C17 C18 C19 122.2(3) . . ? C19 C18 H18 118.9 . . ? C18 C19 C20 117.6(3) . . ? C18 C19 C22 121.8(3) . . ? C20 C19 C22 120.6(3) . . ? C19 C20 H20 119.3 . . ? C21 C20 C19 121.3(3) . . ? C21 C20 H20 119.3 . . ? C16 C21 H21 120.3 . . ? C20 C21 C16 119.4(3) . . ? C20 C21 H21 120.3 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S1 C16 C17 C18 -179.6(2) . . . . ? S1 C16 C21 C20 178.9(2) . . . . ? O1 C5 C6 C1 -169.3(2) . . . . ? O3 S1 N2 N1 57.5(2) . . . . ? O3 S1 C16 C17 -5.7(3) . . . . ? O3 S1 C16 C21 174.2(2) . . . . ? O4 S1 N2 N1 -174.94(18) . . . . ? O4 S1 C16 C17 -136.6(2) . . . . ? O4 S1 C16 C21 43.4(3) . . . . ? N2 S1 C16 C17 111.6(2) . . . . ? N2 S1 C16 C21 -68.4(2) . . . . ? N2 N1 C10 C1 177.8(2) . . . . ? N2 N1 C10 C9 1.1(4) . . . . ? C1 C2 C3 C4 -49.7(3) . . . . ? C1 C2 C3 C11 -175.7(2) . . . . ? C1 C7 C8 C9 33.8(3) . . . . ? C2 C1 C6 C5 -34.1(3) . . . . ? C2 C1 C7 C8 78.3(3) . . . . ? C2 C1 C10 N1 92.6(3) . . . . ? C2 C1 C10 C9 -90.1(3) . . . . ? C2 C3 C4 C5 21.3(4) . . . . ? C2 C3 C11 C12 167.8(4) . . . . ? C2 C3 C11 C13 -69.8(4) . . . . ? C3 C4 C5 O1 175.8(3) . . . . ? C3 C4 C5 C6 -0.2(5) . . . . ? C4 C3 C11 C12 44.8(5) . . . . ? C4 C3 C11 C13 167.2(3) . . . . ? C4 C5 C6 C1 6.9(5) . . . . ? C5 O1 C14 O2 -6.0(6) . . . . ? C5 O1 C14 C15 173.9(3) . . . . ? C6 C1 C2 C3 57.5(3) . . . . ? C6 C1 C7 C8 -158.2(2) . . . . ? C6 C1 C10 N1 -31.0(3) . . . . ? C6 C1 C10 C9 146.3(2) . . . . ? C7 C1 C2 C3 -178.3(2) . . . . ? C7 C1 C6 C5 -157.7(2) . . . . ? C7 C1 C10 N1 -151.0(2) . . . . ? C7 C1 C10 C9 26.3(3) . . . . ? C7 C8 C9 C10 -16.8(3) . . . . ? C8 C9 C10 N1 170.8(3) . . . . ? C8 C9 C10 C1 -6.2(3) . . . . ? C10 N1 N2 S1 160.96(19) . . . . ? C10 C1 C2 C3 -68.3(3) . . . . ? C10 C1 C6 C5 88.5(3) . . . . ? C10 C1 C7 C8 -36.5(3) . . . . ? C11 C3 C4 C5 144.4(4) . . . . ? C14 O1 C5 C4 103.9(4) . . . . ? C14 O1 C5 C6 -79.7(4) . . . . ? C16 S1 N2 N1 -59.5(2) . . . . ? C16 C17 C18 C19 0.6(5) . . . . ? C17 C16 C21 C20 -1.2(4) . . . . ? C17 C18 C19 C20 -0.9(5) . . . . ? C17 C18 C19 C22 179.8(3) . . . . ? C18 C19 C20 C21 0.2(5) . . . . ? C19 C20 C21 C16 0.8(5) . . . . ? C21 C16 C17 C18 0.5(4) . . . . ? C22 C19 C20 C21 179.5(3) . . . . ? _iucr_refine_instructions_details ; TITL zhangy_0518 in P21/n #14 REM reset to P21/n #14 CELL 1.54184 9.961029 17.529489 13.289877 90 101.6672 90 ZERR 4 0.000346 0.000587 0.000446 0 0.0034 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O S UNIT 88 120 8 16 4 L.S. 4 0 0 PLAN 20 BOND $H HTAB CONF fmap 2 53 acta SHEL 999 0.84 REM REM REM WGHT 0.091800 1.079000 FVAR 6.65125 S1 5 0.197981 0.065503 0.068911 11.00000 0.04934 0.04829 = 0.04331 0.00420 -0.00285 -0.00374 O1 4 0.335010 0.386726 0.053555 11.00000 0.07506 0.08300 = 0.07110 -0.01130 -0.00363 -0.00877 O2 4 0.288319 0.501537 -0.016426 11.00000 0.13734 0.07710 = 0.10445 -0.00410 -0.00640 -0.02704 O3 4 0.279141 0.104082 0.153883 11.00000 0.07149 0.07061 = 0.04484 -0.00355 -0.00927 -0.00816 O4 4 0.145757 -0.009168 0.084446 11.00000 0.06327 0.05337 = 0.06011 0.01567 -0.00100 -0.00768 N1 3 0.087558 0.190331 -0.002719 11.00000 0.04790 0.04494 = 0.04640 0.00195 0.01053 -0.00216 N2 3 0.059852 0.115821 0.026165 11.00000 0.04697 0.04814 = 0.05303 0.00376 0.00427 -0.00444 H2 2 0.003860 0.093656 -0.008349 11.00000 0.04783 C1 1 0.002669 0.305717 -0.096406 11.00000 0.04837 0.04899 = 0.04635 0.00366 0.01140 0.00064 C2 1 0.050910 0.304516 -0.199281 11.00000 0.06124 0.05686 = 0.04809 0.00431 0.01368 -0.00621 AFIX 23 H2A 2 -0.009924 0.271962 -0.247096 11.00000 -1.20000 H2B 2 0.044288 0.355675 -0.227677 11.00000 -1.20000 AFIX 0 C3 1 0.197763 0.276024 -0.189511 11.00000 0.06238 0.06413 = 0.06049 -0.00761 0.02572 -0.01023 AFIX 13 H3 2 0.199485 0.221873 -0.170962 11.00000 -1.20000 AFIX 0 C4 1 0.289956 0.318301 -0.102931 11.00000 0.05269 0.07763 = 0.07511 -0.01067 0.01925 -0.00768 AFIX 43 H4 2 0.383488 0.320230 -0.102053 11.00000 -1.20000 AFIX 0 C5 1 0.243443 0.352235 -0.029295 11.00000 0.05815 0.05846 = 0.06092 -0.00627 0.00713 -0.00826 C6 1 0.098028 0.355249 -0.018350 11.00000 0.06671 0.04794 = 0.05432 -0.00257 0.01890 -0.00148 AFIX 23 H6A 2 0.066587 0.407697 -0.026094 11.00000 -1.20000 H6B 2 0.092501 0.338724 0.050351 11.00000 -1.20000 AFIX 0 C7 1 -0.146869 0.332611 -0.111942 11.00000 0.05610 0.06347 = 0.06300 0.01384 0.01531 0.01236 AFIX 23 H7A 2 -0.168343 0.348789 -0.047201 11.00000 -1.20000 H7B 2 -0.163209 0.374921 -0.159905 11.00000 -1.20000 AFIX 0 C8 1 -0.233737 0.263704 -0.154834 11.00000 0.04744 0.07649 = 0.07779 0.01875 0.00448 0.00436 AFIX 23 H8A 2 -0.244564 0.260996 -0.228941 11.00000 -1.20000 H8B 2 -0.323713 0.266273 -0.137588 11.00000 -1.20000 AFIX 0 C9 1 -0.152901 0.194504 -0.103078 11.00000 0.04824 0.06304 = 0.07123 0.01232 0.00270 -0.00582 AFIX 23 H9A 2 -0.193772 0.175026 -0.047895 11.00000 -1.20000 H9B 2 -0.151134 0.154001 -0.152523 11.00000 -1.20000 AFIX 0 C10 1 -0.010274 0.224040 -0.061690 11.00000 0.04432 0.04897 = 0.04462 0.00163 0.01233 0.00004 C11 1 0.240874 0.282683 -0.295285 11.00000 0.08398 0.09084 = 0.07766 -0.01307 0.04173 -0.01888 AFIX 13 H11 2 0.215332 0.333695 -0.322794 11.00000 -1.20000 AFIX 0 C12 1 0.387066 0.272452 -0.291459 11.00000 0.08435 0.19299 = 0.10343 -0.00043 0.03984 0.00590 AFIX 137 H12A 2 0.434990 0.318487 -0.267064 11.00000 -1.50000 H12B 2 0.401751 0.260929 -0.359024 11.00000 -1.50000 H12C 2 0.420724 0.231202 -0.245771 11.00000 -1.50000 AFIX 0 C13 1 0.162432 0.224388 -0.370202 11.00000 0.14043 0.13436 = 0.08359 -0.04761 0.05927 -0.04797 AFIX 137 H13A 2 0.193430 0.173939 -0.349003 11.00000 -1.50000 H13B 2 0.178371 0.234053 -0.437919 11.00000 -1.50000 H13C 2 0.066176 0.228521 -0.370788 11.00000 -1.50000 AFIX 0 C14 1 0.344725 0.463202 0.053468 11.00000 0.07728 0.08349 = 0.07884 -0.02324 0.01250 -0.01919 C15 1 0.433190 0.491199 0.150652 11.00000 0.09421 0.13465 = 0.09036 -0.04294 0.00371 -0.03072 AFIX 137 H15A 2 0.384690 0.486558 0.205855 11.00000 -1.50000 H15B 2 0.456236 0.543735 0.142749 11.00000 -1.50000 H15C 2 0.515577 0.461320 0.165896 11.00000 -1.50000 AFIX 0 C16 1 0.290970 0.061102 -0.030164 11.00000 0.04177 0.04472 = 0.04933 0.00486 -0.00245 0.00210 C17 1 0.414796 0.098234 -0.019743 11.00000 0.05254 0.06650 = 0.06743 -0.00427 0.00019 -0.01532 AFIX 43 H17 2 0.450078 0.125479 0.039779 11.00000 -1.20000 AFIX 0 C18 1 0.485426 0.094642 -0.097860 11.00000 0.04889 0.08078 = 0.08701 0.00516 0.01253 -0.01157 AFIX 43 H18 2 0.569430 0.119446 -0.090055 11.00000 -1.20000 AFIX 0 C19 1 0.436291 0.055493 -0.187773 11.00000 0.05896 0.06361 = 0.06695 0.01388 0.01549 0.01452 C20 1 0.312107 0.018231 -0.196606 11.00000 0.06554 0.08198 = 0.06070 -0.01181 0.00816 -0.00192 AFIX 43 H20 2 0.276790 -0.008721 -0.256374 11.00000 -1.20000 AFIX 0 C21 1 0.239490 0.020229 -0.118501 11.00000 0.05128 0.07380 = 0.06153 -0.01094 0.00396 -0.01305 AFIX 43 H21 2 0.156683 -0.005688 -0.125248 11.00000 -1.20000 AFIX 0 C22 1 0.514511 0.052128 -0.273434 11.00000 0.08774 0.09677 = 0.09073 0.02081 0.03812 0.01982 AFIX 137 H22A 2 0.566359 0.005628 -0.268339 11.00000 -1.50000 H22B 2 0.575713 0.094902 -0.268238 11.00000 -1.50000 H22C 2 0.451350 0.053708 -0.338363 11.00000 -1.50000 HKLF 4 REM zhangy_0518 in P21/n #14 REM R1 = 0.0565 for 3232 Fo > 4sig(Fo) and 0.0666 for all 3890 data REM 270 parameters refined using 0 restraints END WGHT 0.0918 1.0790 REM Highest difference peak 0.856, deepest hole -0.374, 1-sigma level 0.046 Q1 1 0.3148 0.3395 -0.3055 11.00000 0.05 0.86 Q2 1 0.3011 0.2458 -0.2544 11.00000 0.05 0.51 Q3 1 0.1534 0.2416 -0.3823 11.00000 0.05 0.21 Q4 1 0.1287 0.2812 -0.1874 11.00000 0.05 0.21 Q5 1 0.2513 0.2604 -0.1421 11.00000 0.05 0.19 Q6 1 0.2580 0.2054 -0.3371 11.00000 0.05 0.19 Q7 1 0.1401 -0.0349 0.0350 11.00000 0.05 0.18 Q8 1 -0.0631 0.3210 -0.1055 11.00000 0.05 0.18 Q9 1 0.4350 0.0979 -0.1586 11.00000 0.05 0.17 Q10 1 0.5038 0.0965 -0.3043 11.00000 0.05 0.16 Q11 1 0.2827 0.0775 0.1480 11.00000 0.05 0.16 Q12 1 0.3610 0.3797 0.1434 11.00000 0.05 0.15 Q13 1 -0.0820 0.2082 -0.0836 11.00000 0.05 0.15 Q14 1 -0.0657 0.2190 -0.0656 11.00000 0.05 0.14 Q15 1 0.1950 0.0049 0.1006 11.00000 0.05 0.14 Q16 1 0.2615 0.3924 -0.3512 11.00000 0.05 0.14 Q17 1 0.3583 0.2960 -0.0642 11.00000 0.05 0.14 Q18 1 -0.1792 0.1434 -0.1027 11.00000 0.05 0.14 Q19 1 0.2989 0.0221 -0.0459 11.00000 0.05 0.13 Q20 1 0.3955 0.0234 -0.1740 11.00000 0.05 0.13 REM The information below was added by Olex2. REM REM R1 = 0.0565 for 3232 Fo > 4sig(Fo) and 0.0666 for all 8378 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.86, deepest hole -0.37 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0666 REM R1_gt = 0.0565 REM wR_ref = 0.1700 REM GOOF = 1.046 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 8378 REM Reflections_gt = 3232 REM Parameters = n/a REM Hole = -0.37 REM Peak = 0.86 REM Flack = n/a ; _olex2_date_sample_data_collection 2018-05-18 _olex2_submission_special_instructions 'No special instructions were received'