# 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_exp_1114 _database_code_depnum_ccdc_archive 'CCDC 1981382' loop_ _audit_author_name _audit_author_address 'Junliang Zhang' ;East China Normal University China ; _audit_update_record ; 2020-02-02 deposited with the CCDC. 2020-05-29 downloaded from the CCDC. ; _audit_creation_date 2019-12-10 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _shelx_SHELXL_version_number 2017/1 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C25 H23 N O5 S' _chemical_formula_sum 'C25 H23 N O5 S' _chemical_formula_weight 449.50 _chemical_absolute_configuration unk _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' _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 4 _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.91430(10) _cell_length_b 12.5172(3) _cell_length_c 14.5829(3) _cell_angle_alpha 90 _cell_angle_beta 97.421(2) _cell_angle_gamma 90 _cell_volume 1070.54(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 13639 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 74.2160 _cell_measurement_theta_min 4.6380 _shelx_estimated_absorpt_T_max 0.776 _shelx_estimated_absorpt_T_min 0.671 _exptl_absorpt_coefficient_mu 1.667 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.13267 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.28b (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 1.394 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_F_000 472 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.1044 _diffrn_reflns_av_unetI/netI 0.0505 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 20571 _diffrn_reflns_point_group_measured_fraction_full 0.984 _diffrn_reflns_point_group_measured_fraction_max 0.984 _diffrn_reflns_theta_full 67.050 _diffrn_reflns_theta_max 67.050 _diffrn_reflns_theta_min 3.056 _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean ? _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 -7.00 88.00 1.00 1.00 -- 0.00 57.00 30.00 95 2 \w -20.00 16.00 1.00 1.00 -- 0.00 57.00-150.00 36 3 \w 38.00 64.00 1.00 1.00 -- 0.00 38.00 30.00 26 4 \w 16.00 89.00 1.00 1.00 -- 0.00 57.00 -90.00 73 5 \w -23.00 12.00 1.00 1.00 -- 0.00 57.00 -90.00 35 6 \w -23.00 53.00 1.00 1.00 -- 0.00 19.00 90.00 76 7 \w 23.00 59.00 1.00 1.00 -- 0.00 57.00-150.00 36 8 \w -18.00 18.00 1.00 1.00 -- 0.00 38.00 30.00 36 9 \w 5.00 71.00 1.00 1.00 -- 0.00 38.00 -30.00 66 10 \w -19.00 57.00 1.00 1.00 -- 0.00 57.00 150.00 76 11 \w 125.00 185.00 1.00 1.00 -- 95.80 68.00 -31.97 60 12 \w 65.00 91.00 1.00 1.00 -- 95.80 78.00 25.77 26 13 \w 121.00 172.00 1.00 1.00 -- 95.80 78.00 25.77 51 14 \w 75.00 143.00 1.00 1.00 -- 95.80 45.00-180.00 68 15 \w 110.00 185.00 1.00 1.00 -- 95.80 80.00 138.88 75 16 \w 70.00 96.00 1.00 1.00 -- 95.80 68.00 -31.97 26 17 \w 67.00 93.00 1.00 1.00 -- 95.80 71.00 86.65 26 18 \w 64.00 90.00 1.00 1.00 -- 95.80 80.00 138.88 26 19 \w 64.00 90.00 1.00 1.00 -- 95.80 82.00 -30.00 26 20 \w 79.00 127.00 1.00 1.00 -- 95.80 -82.00 150.00 48 21 \w 71.00 97.00 1.00 1.00 -- 95.80 61.00-180.00 26 22 \w 65.00 97.00 1.00 1.00 -- 95.80 77.00 120.00 32 23 \w 75.00 185.00 1.00 1.00 -- 95.80 45.00-120.00 110 24 \w 15.00 126.00 1.00 1.00 -- 95.80 -82.00 30.00 111 25 \w 64.00 90.00 1.00 1.00 -- 95.80 82.00 0.00 26 26 \w 136.00 162.00 1.00 1.00 -- 95.80 82.00 0.00 26 27 \w 64.00 90.00 1.00 1.00 -- 95.80 82.00 -90.00 26 28 \w 43.00 68.00 1.00 1.00 -- 95.80 -82.00-150.00 25 29 \w 86.00 127.00 1.00 1.00 -- 95.80 -82.00-150.00 41 30 \w 137.00 164.00 1.00 1.00 -- 95.80 76.00 51.51 27 31 \w 65.00 91.00 1.00 1.00 -- 95.80 76.00 133.57 26 32 \w 65.00 91.00 1.00 1.00 -- 95.80 77.00 -60.00 26 33 \w 75.00 118.00 1.00 1.00 -- 95.80 45.00 -30.00 43 34 \w 65.00 91.00 1.00 1.00 -- 95.80 77.00-150.00 26 35 \w 65.00 106.00 1.00 1.00 -- 95.80 76.00 51.51 41 36 \w 94.00 185.00 1.00 1.00 -- 95.80 82.00 90.00 91 37 \w 155.00 185.00 1.00 1.00 -- 95.80 45.00 -30.00 30 38 \w 63.00 88.00 1.00 1.00 -- 95.80 82.00 90.00 25 39 \w 39.00 125.00 1.00 1.00 -- 95.80 -82.00 -60.00 86 40 \w 65.00 91.00 1.00 1.00 -- 95.80 77.00-180.00 26 41 \w 75.00 185.00 1.00 1.00 -- 95.80 45.00 60.00 110 42 \w 65.00 91.00 1.00 1.00 -- 95.80 77.00 -90.00 26 43 \w 71.00 97.00 1.00 1.00 -- 95.80 61.00 150.00 26 44 \w 75.00 183.00 1.00 1.00 -- 95.80 45.00-150.00 108 45 \w 75.00 103.00 1.00 1.00 -- 95.80 45.00 30.00 28 46 \w 64.00 126.00 1.00 1.00 -- 95.80 -77.00 60.00 62 47 \w 71.00 105.00 1.00 1.00 -- 95.80 61.00 -90.00 34 48 \w 125.00 183.00 1.00 1.00 -- 95.80 61.00 -90.00 58 49 \w 65.00 90.00 1.00 1.00 -- 95.80 77.00-120.00 25 50 \w 65.00 128.00 1.00 1.00 -- 95.80 77.00 -30.00 63 51 \w 65.00 90.00 1.00 1.00 -- 95.80 77.00 0.00 25 52 \w 63.00 89.00 1.00 1.00 -- 95.80 82.00 30.00 26 53 \w 34.00 59.00 1.00 1.00 -- 95.80 -77.00 60.00 25 54 \w 38.00 127.00 1.00 1.00 -- 95.80 -82.00 120.00 89 55 \w 68.00 94.00 1.00 1.00 -- 95.80 69.00 4.23 26 56 \w 131.00 157.00 1.00 1.00 -- 95.80 71.00 86.65 26 57 \w 134.00 177.00 1.00 1.00 -- 95.80 51.00 -58.52 43 58 \w 71.00 97.00 1.00 1.00 -- 95.80 61.00-120.00 26 59 \w 71.00 123.00 1.00 1.00 -- 95.80 61.00 90.00 52 60 \w 66.00 116.00 1.00 1.00 -- 95.80 77.00 60.00 50 61 \w 74.00 108.00 1.00 1.00 -- 95.80 51.00 -58.52 34 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC12 (RINC): Kappa dual home/near' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.2612602000 _diffrn_orient_matrix_UB_12 0.0004696000 _diffrn_orient_matrix_UB_13 0.0247260000 _diffrn_orient_matrix_UB_21 0.0247815000 _diffrn_orient_matrix_UB_22 0.0513311000 _diffrn_orient_matrix_UB_23 -0.0941722000 _diffrn_orient_matrix_UB_31 -0.0124098000 _diffrn_orient_matrix_UB_32 0.1119236000 _diffrn_orient_matrix_UB_33 0.0430371000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _reflns_Friedel_coverage 0.875 _reflns_Friedel_fraction_full 0.967 _reflns_Friedel_fraction_max 0.967 _reflns_number_gt 3642 _reflns_number_total 3747 _reflns_odcompleteness_completeness 100.00 _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 1.171.39.28b (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.28b (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 'ShelXT (Sheldrick, 2015)' _refine_diff_density_max 0.455 _refine_diff_density_min -0.506 _refine_diff_density_rms 0.073 _refine_ls_abs_structure_details ; Flack x determined using 1620 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.02(2) _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 291 _refine_ls_number_reflns 3747 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0523 _refine_ls_restrained_S_all 1.050 _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^)+(0.1164P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1408 _refine_ls_wR_factor_ref 0.1417 _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: C13(H13), C15(H15), C16(H16) 2.b Secondary CH2 refined with riding coordinates: C14(H14A,H14B) 2.c Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C18(H18), C19(H19), C21(H21), C22(H22) 2.d Idealised Me refined as rotating group: C24(H24A,H24B,H24C), C25(H25A,H25B,H25C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _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 0.50899(15) 0.33082(8) 0.63956(6) 0.0157(3) Uani 1 1 d . . . . . O1 O 0.4103(5) 0.2462(3) 0.58209(19) 0.0222(7) Uani 1 1 d . . . . . O2 O 0.7506(5) 0.3490(3) 0.65010(19) 0.0212(7) Uani 1 1 d . . . . . O3 O 0.1917(5) 0.4180(2) 0.44416(18) 0.0172(6) Uani 1 1 d . . . . . O4 O -0.0630(5) 0.4709(3) -0.0396(2) 0.0269(7) Uani 1 1 d . . . . . O5 O 0.2629(5) 0.5628(3) -0.03407(19) 0.0227(7) Uani 1 1 d . . . . . N1 N 0.3873(6) 0.4408(3) 0.5970(2) 0.0160(7) Uani 1 1 d . . . . . C1 C 0.2198(7) 0.2669(3) 0.7597(3) 0.0166(8) Uani 1 1 d . . . . . H1 H 0.119063 0.249981 0.707412 0.020 Uiso 1 1 calc R . . . . C2 C 0.1613(7) 0.2464(4) 0.8467(3) 0.0183(8) Uani 1 1 d . . . . . H2 H 0.020697 0.215481 0.852251 0.022 Uiso 1 1 calc R . . . . C3 C 0.3096(7) 0.2712(3) 0.9267(3) 0.0181(8) Uani 1 1 d . . . . . C4 C 0.5173(7) 0.3203(4) 0.9156(3) 0.0194(8) Uani 1 1 d . . . . . H4 H 0.616208 0.339379 0.967840 0.023 Uiso 1 1 calc R . . . . C5 C 0.5789(6) 0.3410(3) 0.8292(3) 0.0178(8) Uani 1 1 d . . . . . H5 H 0.718109 0.373213 0.823488 0.021 Uiso 1 1 calc R . . . . C6 C 0.4305(6) 0.3132(3) 0.7505(3) 0.0159(8) Uani 1 1 d . . . . . C7 C 0.4308(7) 0.5443(3) 0.6364(3) 0.0166(8) Uani 1 1 d . . . . . C8 C 0.6242(7) 0.5802(4) 0.6918(3) 0.0192(9) Uani 1 1 d . . . . . H8 H 0.745525 0.534705 0.710848 0.023 Uiso 1 1 calc R . . . . C9 C 0.6286(8) 0.6884(4) 0.7180(3) 0.0230(9) Uani 1 1 d . . . . . H9 H 0.756239 0.715384 0.754642 0.028 Uiso 1 1 calc R . . . . C10 C 0.4465(8) 0.7554(4) 0.6903(3) 0.0256(9) Uani 1 1 d . . . . . H10 H 0.452355 0.826333 0.709297 0.031 Uiso 1 1 calc R . . . . C11 C 0.2556(8) 0.7180(4) 0.6345(3) 0.0238(10) Uani 1 1 d . . . . . H11 H 0.134581 0.763566 0.615201 0.029 Uiso 1 1 calc R . . . . C12 C 0.2473(7) 0.6109(4) 0.6075(3) 0.0175(8) Uani 1 1 d . . . . . C13 C 0.0708(7) 0.5541(4) 0.5425(3) 0.0188(9) Uani 1 1 d . . . . . H13 H -0.079640 0.555895 0.563794 0.023 Uiso 1 1 calc R . . . . C14 C 0.0621(7) 0.5928(4) 0.4418(3) 0.0195(9) Uani 1 1 d . . . . . H14A H -0.089013 0.583740 0.407961 0.023 Uiso 1 1 calc R . . . . H14B H 0.106450 0.667236 0.439194 0.023 Uiso 1 1 calc R . . . . C15 C 0.2340(7) 0.5204(3) 0.4042(3) 0.0167(9) Uani 1 1 d . . . . . H15 H 0.388921 0.544166 0.427036 0.020 Uiso 1 1 calc R . . . . C16 C 0.1635(7) 0.4379(3) 0.5373(3) 0.0168(8) Uani 1 1 d . . . . . H16 H 0.060153 0.385840 0.560086 0.020 Uiso 1 1 calc R . . . . C17 C 0.2077(7) 0.5105(3) 0.3002(3) 0.0174(8) Uani 1 1 d . . . . . C18 C 0.3759(7) 0.5505(3) 0.2517(3) 0.0171(8) Uani 1 1 d . . . . . H18 H 0.508457 0.578808 0.283836 0.020 Uiso 1 1 calc R . . . . C19 C 0.3484(7) 0.5489(3) 0.1549(3) 0.0166(8) Uani 1 1 d . . . . . H19 H 0.462129 0.575751 0.122866 0.020 Uiso 1 1 calc R . . . . C20 C 0.1501(7) 0.5070(3) 0.1072(3) 0.0166(8) Uani 1 1 d . . . . . C21 C -0.0159(7) 0.4634(4) 0.1556(3) 0.0202(9) Uani 1 1 d . . . . . H21 H -0.146144 0.432871 0.123542 0.024 Uiso 1 1 calc R . . . . C22 C 0.0124(7) 0.4653(3) 0.2520(3) 0.0197(9) Uani 1 1 d . . . . . H22 H -0.099131 0.436394 0.284064 0.024 Uiso 1 1 calc R . . . . C23 C 0.1023(7) 0.5091(4) 0.0041(3) 0.0186(8) Uani 1 1 d . . . . . C24 C 0.2212(8) 0.5701(4) -0.1340(3) 0.0284(10) Uani 1 1 d . . . . . H24A H 0.214807 0.499638 -0.160067 0.043 Uiso 1 1 calc GR . . . . H24B H 0.342304 0.609670 -0.156092 0.043 Uiso 1 1 calc GR . . . . H24C H 0.078874 0.606001 -0.151930 0.043 Uiso 1 1 calc GR . . . . C25 C 0.2499(8) 0.2426(4) 1.0206(3) 0.0254(10) Uani 1 1 d . . . . . H25A H 0.087824 0.247248 1.020250 0.038 Uiso 1 1 calc GR . . . . H25B H 0.324230 0.291222 1.065686 0.038 Uiso 1 1 calc GR . . . . H25C H 0.299622 0.171024 1.035866 0.038 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 0.0209(5) 0.0137(5) 0.0138(4) 0.0009(4) 0.0073(3) 0.0028(3) O1 0.0324(16) 0.0186(16) 0.0164(14) -0.0022(12) 0.0067(12) 0.0043(13) O2 0.0200(14) 0.0242(17) 0.0215(13) 0.0027(12) 0.0106(11) 0.0053(12) O3 0.0276(15) 0.0130(15) 0.0125(13) 0.0023(11) 0.0085(11) -0.0001(11) O4 0.0316(17) 0.0310(19) 0.0183(15) -0.0020(13) 0.0040(12) -0.0096(14) O5 0.0287(15) 0.0277(17) 0.0132(14) 0.0007(13) 0.0082(11) -0.0068(14) N1 0.0246(17) 0.0093(16) 0.0150(15) 0.0012(13) 0.0056(13) 0.0034(13) C1 0.0173(17) 0.014(2) 0.0194(19) -0.0001(16) 0.0045(15) 0.0001(15) C2 0.0181(19) 0.016(2) 0.023(2) -0.0004(17) 0.0082(16) -0.0003(16) C3 0.0234(19) 0.013(2) 0.019(2) -0.0003(16) 0.0096(16) 0.0041(16) C4 0.0244(19) 0.019(2) 0.0150(17) 0.0004(17) 0.0022(15) -0.0023(17) C5 0.0183(17) 0.016(2) 0.0191(18) -0.0012(17) 0.0030(14) -0.0021(16) C6 0.0180(17) 0.013(2) 0.0168(18) -0.0020(16) 0.0028(14) 0.0043(15) C7 0.023(2) 0.015(2) 0.0134(18) 0.0011(16) 0.0098(15) -0.0013(16) C8 0.024(2) 0.019(2) 0.0161(19) 0.0005(16) 0.0098(16) 0.0000(16) C9 0.030(2) 0.020(2) 0.021(2) -0.0029(18) 0.0109(17) -0.0078(18) C10 0.038(2) 0.017(2) 0.024(2) -0.0027(18) 0.0121(18) -0.0010(18) C11 0.034(2) 0.019(2) 0.021(2) -0.0014(18) 0.0115(18) 0.0050(17) C12 0.024(2) 0.016(2) 0.0144(18) 0.0048(16) 0.0117(15) 0.0022(16) C13 0.024(2) 0.019(2) 0.0154(19) 0.0004(17) 0.0101(16) 0.0044(17) C14 0.027(2) 0.017(2) 0.016(2) 0.0033(17) 0.0068(16) 0.0047(16) C15 0.027(2) 0.011(2) 0.0138(19) 0.0025(15) 0.0085(16) -0.0022(15) C16 0.021(2) 0.018(2) 0.0128(18) 0.0014(16) 0.0087(15) -0.0002(16) C17 0.026(2) 0.013(2) 0.0147(19) 0.0025(15) 0.0083(16) 0.0016(16) C18 0.0202(19) 0.016(2) 0.0164(19) -0.0003(16) 0.0083(15) -0.0029(16) C19 0.0209(19) 0.013(2) 0.0179(19) 0.0014(16) 0.0101(15) 0.0020(15) C20 0.0244(19) 0.0139(19) 0.0131(18) -0.0003(15) 0.0082(15) 0.0011(15) C21 0.024(2) 0.021(2) 0.0178(19) -0.0034(17) 0.0088(15) -0.0056(17) C22 0.027(2) 0.019(2) 0.0153(18) 0.0006(17) 0.0109(16) -0.0029(17) C23 0.024(2) 0.016(2) 0.017(2) -0.0008(16) 0.0084(16) 0.0004(16) C24 0.042(3) 0.032(3) 0.013(2) 0.0051(19) 0.0124(18) 0.000(2) C25 0.033(2) 0.023(2) 0.023(2) 0.0019(19) 0.0129(18) 0.0014(19) _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 O1 1.428(3) . ? S1 O2 1.436(3) . ? S1 N1 1.638(3) . ? S1 C6 1.753(4) . ? O3 C15 1.443(5) . ? O3 C16 1.412(4) . ? O4 C23 1.196(5) . ? O5 C23 1.342(5) . ? O5 C24 1.449(5) . ? N1 C7 1.428(5) . ? N1 C16 1.488(5) . ? C1 H1 0.9300 . ? C1 C2 1.381(6) . ? C1 C6 1.396(6) . ? C2 H2 0.9300 . ? C2 C3 1.401(6) . ? C3 C4 1.401(6) . ? C3 C25 1.500(6) . ? C4 H4 0.9300 . ? C4 C5 1.381(5) . ? C5 H5 0.9300 . ? C5 C6 1.397(5) . ? C7 C8 1.387(6) . ? C7 C12 1.390(6) . ? C8 H8 0.9300 . ? C8 C9 1.406(6) . ? C9 H9 0.9300 . ? C9 C10 1.383(7) . ? C10 H10 0.9300 . ? C10 C11 1.386(7) . ? C11 H11 0.9300 . ? C11 C12 1.396(7) . ? C12 C13 1.496(6) . ? C13 H13 0.9800 . ? C13 C14 1.541(5) . ? C13 C16 1.560(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 C15 1.517(6) . ? C15 H15 0.9800 . ? C15 C17 1.509(5) . ? C16 H16 0.9800 . ? C17 C18 1.387(6) . ? C17 C22 1.392(6) . ? C18 H18 0.9300 . ? C18 C19 1.400(5) . ? C19 H19 0.9300 . ? C19 C20 1.388(6) . ? C20 C21 1.393(6) . ? C20 C23 1.492(5) . ? C21 H21 0.9300 . ? C21 C22 1.394(6) . ? C22 H22 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 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 O1 S1 O2 120.41(18) . . ? O1 S1 N1 105.96(17) . . ? O1 S1 C6 108.12(19) . . ? O2 S1 N1 106.84(18) . . ? O2 S1 C6 107.45(17) . . ? N1 S1 C6 107.44(18) . . ? C16 O3 C15 106.2(3) . . ? C23 O5 C24 114.3(3) . . ? C7 N1 S1 124.3(3) . . ? C7 N1 C16 111.0(3) . . ? C16 N1 S1 121.0(3) . . ? C2 C1 H1 120.0 . . ? C2 C1 C6 119.9(4) . . ? C6 C1 H1 120.0 . . ? C1 C2 H2 119.4 . . ? C1 C2 C3 121.3(4) . . ? C3 C2 H2 119.4 . . ? C2 C3 C4 117.7(4) . . ? C2 C3 C25 120.8(4) . . ? C4 C3 C25 121.5(4) . . ? C3 C4 H4 119.1 . . ? C5 C4 C3 121.8(4) . . ? C5 C4 H4 119.1 . . ? C4 C5 H5 120.3 . . ? C4 C5 C6 119.4(4) . . ? C6 C5 H5 120.3 . . ? C1 C6 S1 119.2(3) . . ? C1 C6 C5 119.9(4) . . ? C5 C6 S1 120.9(3) . . ? C8 C7 N1 128.3(4) . . ? C8 C7 C12 122.4(4) . . ? C12 C7 N1 109.2(3) . . ? C7 C8 H8 121.5 . . ? C7 C8 C9 117.1(4) . . ? C9 C8 H8 121.5 . . ? C8 C9 H9 119.4 . . ? C10 C9 C8 121.2(4) . . ? C10 C9 H9 119.4 . . ? C9 C10 H10 119.6 . . ? C9 C10 C11 120.8(4) . . ? C11 C10 H10 119.6 . . ? C10 C11 H11 120.5 . . ? C10 C11 C12 119.1(4) . . ? C12 C11 H11 120.5 . . ? C7 C12 C11 119.5(4) . . ? C7 C12 C13 111.2(4) . . ? C11 C12 C13 129.1(4) . . ? C12 C13 H13 112.1 . . ? C12 C13 C14 112.9(4) . . ? C12 C13 C16 104.6(3) . . ? C14 C13 H13 112.1 . . ? C14 C13 C16 102.5(3) . . ? C16 C13 H13 112.1 . . ? C13 C14 H14A 111.3 . . ? C13 C14 H14B 111.3 . . ? H14A C14 H14B 109.2 . . ? C15 C14 C13 102.4(3) . . ? C15 C14 H14A 111.3 . . ? C15 C14 H14B 111.3 . . ? O3 C15 C14 103.1(3) . . ? O3 C15 H15 109.7 . . ? O3 C15 C17 109.4(3) . . ? C14 C15 H15 109.7 . . ? C17 C15 C14 115.2(3) . . ? C17 C15 H15 109.7 . . ? O3 C16 N1 111.1(3) . . ? O3 C16 C13 107.3(3) . . ? O3 C16 H16 111.4 . . ? N1 C16 C13 103.9(3) . . ? N1 C16 H16 111.4 . . ? C13 C16 H16 111.4 . . ? C18 C17 C15 119.7(4) . . ? C18 C17 C22 119.5(4) . . ? C22 C17 C15 120.8(4) . . ? C17 C18 H18 119.6 . . ? C17 C18 C19 120.8(4) . . ? C19 C18 H18 119.6 . . ? C18 C19 H19 120.3 . . ? C20 C19 C18 119.5(4) . . ? C20 C19 H19 120.3 . . ? C19 C20 C21 119.9(4) . . ? C19 C20 C23 122.4(4) . . ? C21 C20 C23 117.6(4) . . ? C20 C21 H21 119.9 . . ? C20 C21 C22 120.3(4) . . ? C22 C21 H21 119.9 . . ? C17 C22 C21 120.0(4) . . ? C17 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? O4 C23 O5 123.6(4) . . ? O4 C23 C20 124.4(4) . . ? O5 C23 C20 112.0(3) . . ? O5 C24 H24A 109.5 . . ? O5 C24 H24B 109.5 . . ? O5 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C3 C25 H25A 109.5 . . ? C3 C25 H25B 109.5 . . ? C3 C25 H25C 109.5 . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? _iucr_refine_instructions_details ; TITL exp_1114_a.res in P2(1) exp_1114.res created by SHELXL-2017/1 at 15:01:29 on 10-Dec-2019 REM Old TITL exp_1114 in P2(1) REM SHELXT solution in P2(1) REM R1 0.093, Rweak 0.031, Alpha 0.003, Orientation as input REM Flack x = -0.023 ( 0.023 ) from Parsons' quotients REM Formula found by SHELXT: C25 N O5 S CELL 1.54184 5.9143 12.5172 14.5829 90 97.421 90 ZERR 2 0.0001 0.0003 0.0003 0 0.002 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O S UNIT 50 46 2 10 2 L.S. 64 PLAN 6 SIZE 0.26 0.22 0.16 BOND $H list 4 fmap 2 53 ACTA SHEL 999 0.837 OMIT 4 -13 1 OMIT 0 5 17 OMIT -1 5 17 OMIT -3 -14 1 OMIT 2 -14 0 OMIT 0 13 9 OMIT -5 -4 14 OMIT -2 -14 1 OMIT -3 -14 3 OMIT 6 2 8 OMIT 1 -14 0 OMIT 1 -6 4 OMIT -1 -1 5 OMIT -2 0 4 OMIT 2 -1 6 OMIT -2 -5 8 REM REM REM WGHT 0.116400 FVAR 0.97733 S1 5 0.508991 0.330819 0.639562 11.00000 0.02094 0.01369 = 0.01376 0.00094 0.00728 0.00281 O1 4 0.410344 0.246150 0.582086 11.00000 0.03245 0.01861 = 0.01640 -0.00220 0.00671 0.00429 O2 4 0.750638 0.349022 0.650100 11.00000 0.02001 0.02423 = 0.02152 0.00275 0.01058 0.00530 O3 4 0.191664 0.417951 0.444156 11.00000 0.02756 0.01299 = 0.01251 0.00225 0.00846 -0.00014 O4 4 -0.063024 0.470879 -0.039578 11.00000 0.03161 0.03096 = 0.01831 -0.00201 0.00403 -0.00961 O5 4 0.262853 0.562811 -0.034066 11.00000 0.02868 0.02767 = 0.01324 0.00073 0.00821 -0.00679 N1 3 0.387344 0.440771 0.597000 11.00000 0.02457 0.00932 = 0.01498 0.00118 0.00564 0.00336 C1 1 0.219848 0.266934 0.759728 11.00000 0.01730 0.01365 = 0.01935 -0.00005 0.00448 0.00005 AFIX 43 H1 2 0.119063 0.249981 0.707412 11.00000 -1.20000 AFIX 0 C2 1 0.161292 0.246376 0.846703 11.00000 0.01809 0.01552 = 0.02275 -0.00043 0.00817 -0.00029 AFIX 43 H2 2 0.020697 0.215481 0.852251 11.00000 -1.20000 AFIX 0 C3 1 0.309588 0.271163 0.926702 11.00000 0.02340 0.01326 = 0.01949 -0.00027 0.00963 0.00405 C4 1 0.517251 0.320253 0.915606 11.00000 0.02439 0.01883 = 0.01495 0.00035 0.00222 -0.00232 AFIX 43 H4 2 0.616208 0.339379 0.967840 11.00000 -1.20000 AFIX 0 C5 1 0.578919 0.340998 0.829194 11.00000 0.01832 0.01615 = 0.01909 -0.00121 0.00298 -0.00214 AFIX 43 H5 2 0.718109 0.373213 0.823488 11.00000 -1.20000 AFIX 0 C6 1 0.430461 0.313182 0.750452 11.00000 0.01804 0.01305 = 0.01680 -0.00200 0.00284 0.00435 C7 1 0.430772 0.544328 0.636413 11.00000 0.02343 0.01486 = 0.01344 0.00105 0.00983 -0.00131 C8 1 0.624165 0.580198 0.691840 11.00000 0.02424 0.01899 = 0.01614 0.00053 0.00977 -0.00001 AFIX 43 H8 2 0.745525 0.534705 0.710848 11.00000 -1.20000 AFIX 0 C9 1 0.628625 0.688386 0.718023 11.00000 0.03050 0.02000 = 0.02064 -0.00293 0.01092 -0.00785 AFIX 43 H9 2 0.756239 0.715384 0.754642 11.00000 -1.20000 AFIX 0 C10 1 0.446525 0.755363 0.690268 11.00000 0.03782 0.01717 = 0.02401 -0.00274 0.01212 -0.00095 AFIX 43 H10 2 0.452355 0.826333 0.709297 11.00000 -1.20000 AFIX 0 C11 1 0.255563 0.717952 0.634454 11.00000 0.03381 0.01865 = 0.02100 -0.00138 0.01149 0.00505 AFIX 43 H11 2 0.134581 0.763566 0.615201 11.00000 -1.20000 AFIX 0 C12 1 0.247251 0.610889 0.607522 11.00000 0.02407 0.01638 = 0.01445 0.00479 0.01174 0.00217 C13 1 0.070798 0.554123 0.542461 11.00000 0.02420 0.01886 = 0.01545 0.00044 0.01014 0.00437 AFIX 13 H13 2 -0.079640 0.555895 0.563794 11.00000 -1.20000 AFIX 0 C14 1 0.062091 0.592801 0.441781 11.00000 0.02655 0.01662 = 0.01634 0.00333 0.00683 0.00467 AFIX 23 H14A 2 -0.089013 0.583740 0.407961 11.00000 -1.20000 H14B 2 0.106450 0.667236 0.439194 11.00000 -1.20000 AFIX 0 C15 1 0.233994 0.520351 0.404218 11.00000 0.02661 0.01121 = 0.01384 0.00251 0.00851 -0.00219 AFIX 13 H15 2 0.388921 0.544166 0.427036 11.00000 -1.20000 AFIX 0 C16 1 0.163518 0.437860 0.537318 11.00000 0.02111 0.01814 = 0.01277 0.00136 0.00870 -0.00020 AFIX 13 H16 2 0.060153 0.385840 0.560086 11.00000 -1.20000 AFIX 0 C17 1 0.207718 0.510473 0.300229 11.00000 0.02572 0.01337 = 0.01471 0.00250 0.00835 0.00157 C18 1 0.375864 0.550532 0.251701 11.00000 0.02016 0.01614 = 0.01641 -0.00026 0.00829 -0.00288 AFIX 43 H18 2 0.508457 0.578808 0.283836 11.00000 -1.20000 AFIX 0 C19 1 0.348382 0.548913 0.154904 11.00000 0.02089 0.01288 = 0.01789 0.00139 0.01007 0.00201 AFIX 43 H19 2 0.462129 0.575751 0.122866 11.00000 -1.20000 AFIX 0 C20 1 0.150091 0.506951 0.107153 11.00000 0.02435 0.01392 = 0.01305 -0.00029 0.00824 0.00110 C21 1 -0.015889 0.463374 0.155612 11.00000 0.02379 0.02071 = 0.01779 -0.00336 0.00881 -0.00564 AFIX 43 H21 2 -0.146144 0.432871 0.123542 11.00000 -1.20000 AFIX 0 C22 1 0.012434 0.465295 0.251981 11.00000 0.02657 0.01924 = 0.01534 0.00061 0.01094 -0.00292 AFIX 43 H22 2 -0.099131 0.436394 0.284064 11.00000 -1.20000 AFIX 0 C23 1 0.102279 0.509114 0.004143 11.00000 0.02433 0.01596 = 0.01706 -0.00080 0.00840 0.00036 C24 1 0.221197 0.570149 -0.133963 11.00000 0.04220 0.03215 = 0.01328 0.00513 0.01238 -0.00031 AFIX 137 H24A 2 0.214807 0.499638 -0.160067 11.00000 -1.50000 H24B 2 0.342304 0.609670 -0.156092 11.00000 -1.50000 H24C 2 0.078874 0.606001 -0.151930 11.00000 -1.50000 AFIX 0 C25 1 0.249946 0.242592 1.020579 11.00000 0.03260 0.02279 = 0.02323 0.00189 0.01287 0.00138 AFIX 137 H25A 2 0.087824 0.247248 1.020250 11.00000 -1.50000 H25B 2 0.324230 0.291222 1.065686 11.00000 -1.50000 H25C 2 0.299622 0.171024 1.035866 11.00000 -1.50000 AFIX 0 HKLF 4 REM exp_1114_a.res in P2(1) REM R1 = 0.0523 for 3642 Fo > 4sig(Fo) and 0.0532 for all 3747 data REM 291 parameters refined using 1 restraints END WGHT 0.1166 0.0000 REM Highest difference peak 0.455, deepest hole -0.506, 1-sigma level 0.073 Q1 1 0.6348 0.3314 0.7518 11.00000 0.05 0.45 Q2 1 0.5202 0.3937 0.7811 11.00000 0.05 0.36 Q3 1 0.5179 0.2600 0.5011 11.00000 0.05 0.30 Q4 1 0.3994 0.3240 0.5184 11.00000 0.05 0.30 Q5 1 0.5995 0.3433 0.5563 11.00000 0.05 0.29 Q6 1 0.4972 0.4016 0.4990 11.00000 0.05 0.28 REM The information below was added by Olex2. REM REM R1 = 0.0523 for 3642 Fo > 4sig(Fo) and 0.0532 for all 21798 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.45, deepest hole -0.51 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0532 REM R1_gt = 0.0523 REM wR_ref = 0.1417 REM GOOF = 1.050 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 21798 REM Reflections_gt = 3642 REM Parameters = n/a REM Hole = -0.51 REM Peak = 0.45 REM Flack = -0.02(2) ; _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 3.234 _oxdiff_exptl_absorpt_empirical_full_min 0.352 ####################################################################### # # 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_exp_815 _database_code_depnum_ccdc_archive 'CCDC 1981384' loop_ _audit_author_name _audit_author_address 'Junliang Zhang' ;East China Normal University China ; _audit_update_record ; 2020-02-02 deposited with the CCDC. 2020-05-29 downloaded from the CCDC. ; _audit_creation_date 2019-05-13 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _shelx_SHELXL_version_number 2016/6 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety '2(C17 H17 N O3 S)' _chemical_formula_sum 'C34 H34 N2 O6 S2' _chemical_formula_weight 630.75 _chemical_absolute_configuration ad _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' _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 orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.90430(10) _cell_length_b 10.79480(10) _cell_length_c 31.6319(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3040.46(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 39460 _cell_measurement_temperature 100.0(4) _cell_measurement_theta_max 74.2070 _cell_measurement_theta_min 4.3100 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _exptl_absorpt_coefficient_mu 1.998 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.23950 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017) 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 1.378 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_F_000 1328 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0768 _diffrn_reflns_av_unetI/netI 0.0289 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_number 75990 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.528 _diffrn_reflns_theta_min 4.328 _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.0(4) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.992 _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 30.00 74.00 1.00 1.00 -- 0.00 38.00 60.00 44 2 \w -19.00 82.00 1.00 1.00 -- 0.00 38.00-150.00 101 3 \w 60.00 88.00 1.00 1.00 -- 0.00 77.00 -30.00 28 4 \w -26.00 20.00 1.00 1.00 -- 0.00 -19.00 -60.00 46 5 \w -71.00 -45.00 1.00 1.00 -- 0.00 -19.00 -60.00 26 6 \w -14.00 26.00 1.00 1.00 -- 0.00 38.00 60.00 40 7 \w -17.00 56.00 1.00 1.00 -- 0.00 38.00 -30.00 73 8 \w -28.00 -3.00 1.00 1.00 -- 0.00 77.00 -30.00 25 9 \w -30.00 87.00 1.00 1.00 -- 0.00 82.00 -90.00 117 10 \w -73.00 -33.00 1.00 1.00 -- 0.00 -57.00 -60.00 40 11 \w -16.00 21.00 1.00 1.00 -- 0.00 -57.00 -60.00 37 12 \w -13.00 79.00 1.00 1.00 -- 0.00 38.00 120.00 92 13 \w 24.00 49.00 1.00 1.00 -- 0.00 77.00 -30.00 25 14 \w 63.00 88.00 1.00 1.00 -- 95.80 81.00 136.93 25 15 \w 72.00 180.00 1.00 1.00 -- 95.80 57.00 -44.20 108 16 \w 152.00 178.00 1.00 1.00 -- 95.80 78.00 52.49 26 17 \w 71.00 163.00 1.00 1.00 -- 95.80 58.00-103.70 92 18 \w 132.00 185.00 1.00 1.00 -- 95.80 79.00-156.68 53 19 \w 65.00 96.00 1.00 1.00 -- 95.80 78.00 52.49 31 20 \w 75.00 121.00 1.00 1.00 -- 95.80 45.00 170.13 46 21 \w 31.00 107.00 1.00 1.00 -- 95.80 -82.00 60.00 76 22 \w 64.00 89.00 1.00 1.00 -- 95.80 79.00-156.68 25 23 \w 65.00 90.00 1.00 1.00 -- 95.80 77.00-180.00 25 24 \w 63.00 98.00 1.00 1.00 -- 95.80 82.00 30.00 35 25 \w 102.00 128.00 1.00 1.00 -- 95.80 82.00 30.00 26 26 \w 65.00 90.00 1.00 1.00 -- 95.80 77.00 0.00 25 27 \w 118.00 185.00 1.00 1.00 -- 95.80 77.00 0.00 67 28 \w 63.00 88.00 1.00 1.00 -- 95.80 82.00 60.00 25 29 \w 105.00 184.00 1.00 1.00 -- 95.80 82.00 60.00 79 30 \w 63.00 89.00 1.00 1.00 -- 95.80 82.00-120.00 26 31 \w 6.00 128.00 1.00 1.00 -- 95.80 -82.00 120.00 122 32 \w 64.00 127.00 1.00 1.00 -- 95.80 -82.00 -90.00 63 33 \w 146.00 172.00 1.00 1.00 -- 95.80 79.00 -40.56 26 34 \w 153.00 184.00 1.00 1.00 -- 95.80 70.00 90.93 31 35 \w 117.00 183.00 1.00 1.00 -- 95.80 82.00 150.00 66 36 \w 63.00 93.00 1.00 1.00 -- 95.80 82.00 150.00 30 37 \w 11.00 58.00 1.00 1.00 -- 95.80 -82.00 -90.00 47 38 \w 63.00 88.00 1.00 1.00 -- 95.80 82.00 -90.00 25 39 \w 71.00 108.00 1.00 1.00 -- 95.80 61.00-150.00 37 40 \w 65.00 91.00 1.00 1.00 -- 95.80 77.00 90.00 26 41 \w 65.00 90.00 1.00 1.00 -- 95.80 77.00-120.00 25 42 \w 65.00 167.00 1.00 1.00 -- 95.80 77.00 -30.00 102 43 \w 52.00 78.00 1.00 1.00 -- 95.80 -82.00 -30.00 26 44 \w 18.00 120.00 1.00 1.00 -- 95.80 -61.00 120.00 102 45 \w 64.00 113.00 1.00 1.00 -- 95.80 79.00 -40.56 49 46 \w 71.00 123.00 1.00 1.00 -- 95.80 61.00-120.00 52 47 \w 65.00 90.00 1.00 1.00 -- 95.80 77.00 30.00 25 48 \w 63.00 89.00 1.00 1.00 -- 95.80 82.00 120.00 26 49 \w 75.00 156.00 1.00 1.00 -- 95.80 45.00-150.00 81 50 \w 65.00 91.00 1.00 1.00 -- 95.80 77.00 -90.00 26 51 \w 63.00 88.00 1.00 1.00 -- 95.80 82.00 0.00 25 52 \w 119.00 144.00 1.00 1.00 -- 95.80 82.00 0.00 25 53 \w 75.00 101.00 1.00 1.00 -- 95.80 61.00 90.00 26 54 \w 114.00 181.00 1.00 1.00 -- 95.80 61.00 90.00 67 55 \w 113.00 138.00 1.00 1.00 -- 95.80 77.00 120.00 25 56 \w 75.00 100.00 1.00 1.00 -- 95.80 45.00 30.00 25 57 \w 75.00 103.00 1.00 1.00 -- 95.80 45.00 90.00 28 58 \w 63.00 88.00 1.00 1.00 -- 95.80 82.00 90.00 25 59 \w 63.00 89.00 1.00 1.00 -- 95.80 81.00 -57.09 26 60 \w 71.00 97.00 1.00 1.00 -- 95.80 59.00 134.30 26 61 \w 63.00 89.00 1.00 1.00 -- 95.80 82.00 -30.00 26 62 \w 65.00 90.00 1.00 1.00 -- 95.80 77.00 -60.00 25 63 \w 65.00 90.00 1.00 1.00 -- 95.80 77.00 120.00 25 64 \w 140.00 174.00 1.00 1.00 -- 95.80 45.00 120.00 34 65 \w 76.00 103.00 1.00 1.00 -- 95.80 45.00 120.00 27 66 \w 103.00 128.00 1.00 1.00 -- 95.80 82.00-120.00 25 67 \w 120.00 185.00 1.00 1.00 -- 95.80 81.00 136.93 65 68 \w 93.00 119.00 1.00 1.00 -- 95.80 -82.00-180.00 26 69 \w 75.00 114.00 1.00 1.00 -- 95.80 45.00 -60.00 39 70 \w 68.00 167.00 1.00 1.00 -- 95.80 69.00 25.48 99 71 \w 68.00 93.00 1.00 1.00 -- 95.80 70.00 90.93 25 72 \w 130.00 165.00 1.00 1.00 -- 95.80 44.00-163.69 35 73 \w 82.00 111.00 1.00 1.00 -- 95.80 -82.00 -30.00 29 74 \w 76.00 102.00 1.00 1.00 -- 95.80 44.00-163.69 26 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC12 (RINC): Kappa dual home/near' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0112666000 _diffrn_orient_matrix_UB_12 0.0916480000 _diffrn_orient_matrix_UB_13 0.0371948000 _diffrn_orient_matrix_UB_21 0.0000644000 _diffrn_orient_matrix_UB_22 -0.1092103000 _diffrn_orient_matrix_UB_23 0.0313264000 _diffrn_orient_matrix_UB_31 0.1727098000 _diffrn_orient_matrix_UB_32 0.0060697000 _diffrn_orient_matrix_UB_33 0.0024052000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _reflns_Friedel_coverage 0.758 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.990 _reflns_number_gt 6061 _reflns_number_total 6165 _reflns_odcompleteness_completeness 99.81 _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 1.171.39.32a (Rigaku OD, 2017)' _computing_data_collection 'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)' _computing_data_reduction 'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)' _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 'ShelXT (Sheldrick, 2015)' _refine_diff_density_max 0.180 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.045 _refine_ls_abs_structure_details ; Flack x determined using 2534 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.013(5) _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 399 _refine_ls_number_reflns 6165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0306 _refine_ls_R_factor_gt 0.0300 _refine_ls_restrained_S_all 1.036 _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^)+(0.0380P)^2^+0.9283P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0748 _refine_ls_wR_factor_ref 0.0751 _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: C7(H7), C8(H8), C24(H24), C27(H27) 2.b Secondary CH2 refined with riding coordinates: C9(H9A,H9B), C10(H10A,H10B), C25(H25A,H25B), C26(H26A,H26B) 2.c Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C29(H29), C30(H30), C32(H32), C33(H33) 2.d Idealised Me refined as rotating group: C17(H17A,H17B,H17C), C34(H34A,H34B,H34C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _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 -0.29512(6) 0.47038(5) 0.53635(2) 0.02276(13) Uani 1 1 d . . . . . O1 O 0.0365(2) 0.43288(15) 0.49807(5) 0.0281(4) Uani 1 1 d . . . . . O2 O -0.3149(2) 0.40020(16) 0.49840(5) 0.0287(4) Uani 1 1 d . . . . . O3 O -0.4167(2) 0.54257(16) 0.55291(5) 0.0286(4) Uani 1 1 d . . . . . N1 N -0.1575(2) 0.56679(18) 0.52608(6) 0.0240(4) Uani 1 1 d . . . . . C1 C -0.1046(3) 0.6611(2) 0.55374(7) 0.0219(5) Uani 1 1 d . . . . . C2 C -0.1657(3) 0.7030(2) 0.59163(7) 0.0254(5) Uani 1 1 d . . . . . H2 H -0.252092 0.667571 0.602889 0.030 Uiso 1 1 calc R . . . . C3 C -0.0926(3) 0.7998(2) 0.61197(7) 0.0276(5) Uani 1 1 d . . . . . H3 H -0.130350 0.828989 0.637512 0.033 Uiso 1 1 calc R . . . . C4 C 0.0355(3) 0.8540(2) 0.59505(8) 0.0284(5) Uani 1 1 d . . . . . H4 H 0.082175 0.918947 0.609232 0.034 Uiso 1 1 calc R . . . . C5 C 0.0944(3) 0.8114(2) 0.55683(8) 0.0274(5) Uani 1 1 d . . . . . H5 H 0.179893 0.847655 0.545303 0.033 Uiso 1 1 calc R . . . . C6 C 0.0236(3) 0.7144(2) 0.53638(7) 0.0226(5) Uani 1 1 d . . . . . C7 C 0.0651(3) 0.6521(2) 0.49523(7) 0.0243(5) Uani 1 1 d . . . . . H7 H 0.055621 0.708666 0.471133 0.029 Uiso 1 1 calc R . . . . C8 C -0.0462(3) 0.5427(2) 0.49217(7) 0.0244(5) Uani 1 1 d . . . . . H8 H -0.095522 0.542135 0.464478 0.029 Uiso 1 1 calc R . . . . C9 C 0.1804(3) 0.4642(2) 0.51576(8) 0.0296(5) Uani 1 1 d . . . . . H9A H 0.255019 0.402244 0.508534 0.035 Uiso 1 1 calc R . . . . H9B H 0.174450 0.471000 0.546291 0.035 Uiso 1 1 calc R . . . . C10 C 0.2187(3) 0.5878(2) 0.49603(8) 0.0297(5) Uani 1 1 d . . . . . H10A H 0.258979 0.577675 0.467746 0.036 Uiso 1 1 calc R . . . . H10B H 0.290257 0.633324 0.513165 0.036 Uiso 1 1 calc R . . . . C11 C -0.2329(3) 0.3709(2) 0.57701(7) 0.0230(5) Uani 1 1 d . . . . . C12 C -0.2824(3) 0.3897(2) 0.61837(7) 0.0256(5) Uani 1 1 d . . . . . H12 H -0.344664 0.456229 0.624855 0.031 Uiso 1 1 calc R . . . . C13 C -0.2373(3) 0.3079(2) 0.64959(7) 0.0269(5) Uani 1 1 d . . . . . H13 H -0.269202 0.320902 0.677240 0.032 Uiso 1 1 calc R . . . . C14 C -0.1456(3) 0.2067(2) 0.64074(7) 0.0243(5) Uani 1 1 d . . . . . C15 C -0.0961(3) 0.1917(2) 0.59912(8) 0.0259(5) Uani 1 1 d . . . . . H15 H -0.032824 0.125771 0.592670 0.031 Uiso 1 1 calc R . . . . C16 C -0.1387(3) 0.2723(2) 0.56719(7) 0.0251(5) Uani 1 1 d . . . . . H16 H -0.104875 0.260672 0.539662 0.030 Uiso 1 1 calc R . . . . C17 C -0.1041(3) 0.1161(2) 0.67491(8) 0.0300(5) Uani 1 1 d . . . . . H17A H -0.064903 0.160178 0.698838 0.045 Uiso 1 1 calc GR . . . . H17B H -0.029306 0.059886 0.664424 0.045 Uiso 1 1 calc GR . . . . H17C H -0.191657 0.070315 0.683262 0.045 Uiso 1 1 calc GR . . . . S2 S 0.44466(6) 0.89248(5) 0.72696(2) 0.02031(12) Uani 1 1 d . . . . . O4 O 0.4880(2) 0.69132(17) 0.65445(6) 0.0327(4) Uani 1 1 d . . . . . O5 O 0.59833(18) 0.85579(17) 0.72984(6) 0.0302(4) Uani 1 1 d . . . . . O6 O 0.37195(19) 0.94789(15) 0.76271(5) 0.0244(3) Uani 1 1 d . . . . . N2 N 0.3514(2) 0.76716(17) 0.71517(6) 0.0202(4) Uani 1 1 d . . . . . C18 C 0.1925(2) 0.7539(2) 0.71632(6) 0.0183(4) Uani 1 1 d . . . . . C19 C 0.0855(3) 0.8362(2) 0.73102(7) 0.0218(4) Uani 1 1 d . . . . . H19 H 0.112187 0.913755 0.741379 0.026 Uiso 1 1 calc R . . . . C20 C -0.0637(3) 0.7983(2) 0.72971(7) 0.0254(5) Uani 1 1 d . . . . . H20 H -0.138096 0.851636 0.739400 0.030 Uiso 1 1 calc R . . . . C21 C -0.1042(3) 0.6825(2) 0.71425(7) 0.0257(5) Uani 1 1 d . . . . . H21 H -0.204672 0.658831 0.713849 0.031 Uiso 1 1 calc R . . . . C22 C 0.0055(3) 0.6022(2) 0.69942(7) 0.0263(5) Uani 1 1 d . . . . . H22 H -0.021096 0.525078 0.688682 0.032 Uiso 1 1 calc R . . . . C23 C 0.1546(3) 0.6376(2) 0.70070(7) 0.0212(5) Uani 1 1 d . . . . . C24 C 0.2919(3) 0.5704(2) 0.68509(9) 0.0310(6) Uani 1 1 d . . . . . H24 H 0.305400 0.490132 0.699041 0.037 Uiso 1 1 calc R . . . . C25 C 0.2956(4) 0.5594(3) 0.63641(11) 0.0549(10) Uani 1 1 d . . . . . H25A H 0.352357 0.487224 0.627530 0.066 Uiso 1 1 calc R . . . . H25B H 0.194903 0.554381 0.624813 0.066 Uiso 1 1 calc R . . . . C26 C 0.3719(3) 0.6766(4) 0.62327(9) 0.0475(8) Uani 1 1 d . . . . . H26A H 0.414174 0.669015 0.595128 0.057 Uiso 1 1 calc R . . . . H26B H 0.302717 0.745973 0.623779 0.057 Uiso 1 1 calc R . . . . C27 C 0.4241(3) 0.6598(2) 0.69383(8) 0.0244(5) Uani 1 1 d . . . . . H27 H 0.498764 0.621073 0.712344 0.029 Uiso 1 1 calc R . . . . C28 C 0.4245(3) 0.9958(2) 0.68417(7) 0.0207(4) Uani 1 1 d . . . . . C29 C 0.5178(3) 0.9831(2) 0.64912(8) 0.0254(5) Uani 1 1 d . . . . . H29 H 0.590298 0.921157 0.648252 0.030 Uiso 1 1 calc R . . . . C30 C 0.5006(3) 1.0643(2) 0.61553(7) 0.0272(5) Uani 1 1 d . . . . . H30 H 0.563643 1.057055 0.592213 0.033 Uiso 1 1 calc R . . . . C31 C 0.3918(3) 1.1563(2) 0.61587(7) 0.0269(5) Uani 1 1 d . . . . . C32 C 0.3006(3) 1.1671(2) 0.65146(8) 0.0305(5) Uani 1 1 d . . . . . H32 H 0.227055 1.228237 0.652194 0.037 Uiso 1 1 calc R . . . . C33 C 0.3172(3) 1.0886(2) 0.68577(8) 0.0273(5) Uani 1 1 d . . . . . H33 H 0.257166 1.098162 0.709594 0.033 Uiso 1 1 calc R . . . . C34 C 0.3707(4) 1.2417(2) 0.57878(8) 0.0345(6) Uani 1 1 d . . . . . H34A H 0.401023 1.323951 0.586495 0.052 Uiso 1 1 calc GR . . . . H34B H 0.266773 1.242260 0.570657 0.052 Uiso 1 1 calc GR . . . . H34C H 0.430677 1.213308 0.555498 0.052 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 0.0219(3) 0.0235(3) 0.0229(3) -0.0008(2) 0.0025(2) 0.0020(2) O1 0.0299(10) 0.0241(8) 0.0304(8) 0.0001(7) 0.0057(7) 0.0058(7) O2 0.0298(10) 0.0316(9) 0.0246(8) -0.0046(7) -0.0026(7) -0.0002(8) O3 0.0245(9) 0.0292(9) 0.0320(8) 0.0014(7) 0.0054(7) 0.0058(7) N1 0.0262(11) 0.0245(9) 0.0214(9) -0.0028(7) 0.0060(8) 0.0004(8) C1 0.0270(13) 0.0191(10) 0.0195(10) 0.0022(8) 0.0003(9) 0.0045(9) C2 0.0305(14) 0.0236(11) 0.0221(11) 0.0024(9) 0.0047(10) 0.0043(10) C3 0.0385(15) 0.0229(11) 0.0215(11) -0.0009(9) -0.0022(10) 0.0063(10) C4 0.0336(14) 0.0212(11) 0.0305(12) -0.0011(9) -0.0076(10) 0.0031(10) C5 0.0266(13) 0.0237(11) 0.0318(12) 0.0048(9) -0.0004(10) 0.0012(10) C6 0.0242(12) 0.0217(11) 0.0219(10) 0.0049(9) 0.0009(9) 0.0045(9) C7 0.0272(13) 0.0247(11) 0.0209(10) 0.0067(9) 0.0039(9) 0.0018(10) C8 0.0278(13) 0.0267(11) 0.0185(10) 0.0006(9) 0.0040(9) 0.0063(10) C9 0.0322(14) 0.0323(13) 0.0242(11) 0.0015(10) 0.0020(10) 0.0115(12) C10 0.0258(13) 0.0354(13) 0.0278(12) -0.0001(10) 0.0054(10) 0.0039(11) C11 0.0252(12) 0.0217(11) 0.0222(11) -0.0007(9) 0.0020(9) -0.0003(9) C12 0.0253(12) 0.0249(11) 0.0267(11) -0.0044(9) 0.0052(10) 0.0016(10) C13 0.0301(14) 0.0293(12) 0.0213(11) -0.0034(10) 0.0026(9) -0.0009(10) C14 0.0249(12) 0.0226(11) 0.0253(11) -0.0019(9) -0.0011(9) -0.0041(9) C15 0.0262(13) 0.0235(11) 0.0279(11) -0.0011(9) 0.0015(10) 0.0033(10) C16 0.0295(13) 0.0228(11) 0.0231(11) -0.0020(9) 0.0055(9) 0.0021(10) C17 0.0341(14) 0.0302(12) 0.0257(11) 0.0018(10) -0.0031(10) -0.0003(11) S2 0.0137(3) 0.0250(3) 0.0222(2) -0.0003(2) -0.00305(19) -0.0018(2) O4 0.0276(10) 0.0379(10) 0.0325(9) -0.0021(8) 0.0057(7) 0.0097(8) O5 0.0135(8) 0.0397(9) 0.0374(9) 0.0047(8) -0.0078(7) -0.0017(7) O6 0.0249(9) 0.0281(8) 0.0204(8) -0.0031(6) -0.0004(6) -0.0051(7) N2 0.0132(9) 0.0209(9) 0.0265(9) -0.0015(7) -0.0012(7) 0.0022(7) C18 0.0144(11) 0.0225(10) 0.0182(10) 0.0021(8) -0.0019(8) -0.0002(9) C19 0.0182(11) 0.0258(11) 0.0215(10) -0.0013(9) 0.0009(9) 0.0007(9) C20 0.0178(12) 0.0357(12) 0.0226(10) 0.0029(10) 0.0020(9) 0.0026(10) C21 0.0154(11) 0.0377(13) 0.0241(11) 0.0085(9) -0.0010(9) -0.0066(10) C22 0.0261(13) 0.0270(11) 0.0259(11) 0.0047(10) -0.0041(9) -0.0070(10) C23 0.0214(11) 0.0187(10) 0.0234(11) 0.0016(8) -0.0016(9) -0.0009(9) C24 0.0257(13) 0.0208(11) 0.0464(15) -0.0082(10) -0.0036(12) 0.0050(10) C25 0.0323(17) 0.074(2) 0.058(2) -0.0452(18) 0.0005(15) 0.0090(16) C26 0.0349(17) 0.079(2) 0.0280(13) -0.0159(14) 0.0018(12) 0.0191(16) C27 0.0190(12) 0.0229(11) 0.0314(12) 0.0019(9) 0.0004(9) 0.0078(9) C28 0.0151(11) 0.0231(11) 0.0239(10) -0.0015(8) -0.0021(8) -0.0025(8) C29 0.0182(12) 0.0276(12) 0.0303(12) -0.0028(9) 0.0019(9) -0.0003(9) C30 0.0273(13) 0.0307(12) 0.0238(11) -0.0025(10) 0.0052(9) -0.0057(10) C31 0.0329(14) 0.0227(11) 0.0250(11) -0.0015(9) -0.0040(10) -0.0100(10) C32 0.0305(14) 0.0275(12) 0.0335(12) 0.0004(10) 0.0008(11) 0.0064(11) C33 0.0262(13) 0.0287(12) 0.0271(11) -0.0006(9) 0.0055(10) 0.0017(10) C34 0.0519(18) 0.0231(11) 0.0285(13) 0.0013(10) -0.0052(12) -0.0097(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 S1 O2 1.4303(17) . ? S1 O3 1.4333(17) . ? S1 N1 1.640(2) . ? S1 C11 1.765(2) . ? O1 C8 1.408(3) . ? O1 C9 1.439(3) . ? N1 C1 1.422(3) . ? N1 C8 1.483(3) . ? C1 C2 1.392(3) . ? C1 C6 1.392(3) . ? C2 H2 0.9300 . ? C2 C3 1.389(4) . ? C3 H3 0.9300 . ? C3 C4 1.390(4) . ? C4 H4 0.9300 . ? C4 C5 1.396(3) . ? C5 H5 0.9300 . ? C5 C6 1.383(3) . ? C6 C7 1.511(3) . ? C7 H7 0.9800 . ? C7 C8 1.546(3) . ? C7 C10 1.534(3) . ? C8 H8 0.9800 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 C10 1.512(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.395(3) . ? C11 C16 1.390(3) . ? C12 H12 0.9300 . ? C12 C13 1.384(3) . ? C13 H13 0.9300 . ? C13 C14 1.392(3) . ? C14 C15 1.398(3) . ? C14 C17 1.504(3) . ? C15 H15 0.9300 . ? C15 C16 1.386(3) . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? S2 O5 1.4274(17) . ? S2 O6 1.4337(16) . ? S2 N2 1.6307(19) . ? S2 C28 1.763(2) . ? O4 C26 1.437(3) . ? O4 C27 1.411(3) . ? N2 C18 1.422(3) . ? N2 C27 1.489(3) . ? C18 C19 1.383(3) . ? C18 C23 1.391(3) . ? C19 H19 0.9300 . ? C19 C20 1.390(3) . ? C20 H20 0.9300 . ? C20 C21 1.390(4) . ? C21 H21 0.9300 . ? C21 C22 1.388(4) . ? C22 H22 0.9300 . ? C22 C23 1.382(3) . ? C23 C24 1.505(3) . ? C24 H24 0.9800 . ? C24 C25 1.545(4) . ? C24 C27 1.547(3) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C25 C26 1.495(5) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 H27 0.9800 . ? C28 C29 1.392(3) . ? C28 C33 1.386(3) . ? C29 H29 0.9300 . ? C29 C30 1.386(3) . ? C30 H30 0.9300 . ? C30 C31 1.387(4) . ? C31 C32 1.393(4) . ? C31 C34 1.504(3) . ? C32 H32 0.9300 . ? C32 C33 1.385(4) . ? C33 H33 0.9300 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 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 O3 120.13(11) . . ? O2 S1 N1 105.17(10) . . ? O2 S1 C11 109.14(11) . . ? O3 S1 N1 106.97(10) . . ? O3 S1 C11 107.56(11) . . ? N1 S1 C11 107.20(11) . . ? C8 O1 C9 108.64(18) . . ? C1 N1 S1 125.42(16) . . ? C1 N1 C8 110.45(19) . . ? C8 N1 S1 122.07(16) . . ? C2 C1 N1 129.3(2) . . ? C6 C1 N1 109.0(2) . . ? C6 C1 C2 121.7(2) . . ? C1 C2 H2 121.3 . . ? C3 C2 C1 117.4(2) . . ? C3 C2 H2 121.3 . . ? C2 C3 H3 119.2 . . ? C2 C3 C4 121.5(2) . . ? C4 C3 H3 119.2 . . ? C3 C4 H4 119.9 . . ? C3 C4 C5 120.2(2) . . ? C5 C4 H4 119.9 . . ? C4 C5 H5 120.6 . . ? C6 C5 C4 118.9(2) . . ? C6 C5 H5 120.6 . . ? C1 C6 C7 110.9(2) . . ? C5 C6 C1 120.2(2) . . ? C5 C6 C7 128.9(2) . . ? C6 C7 H7 111.8 . . ? C6 C7 C8 103.72(18) . . ? C6 C7 C10 113.9(2) . . ? C8 C7 H7 111.8 . . ? C10 C7 H7 111.8 . . ? C10 C7 C8 103.09(19) . . ? O1 C8 N1 113.66(18) . . ? O1 C8 C7 107.5(2) . . ? O1 C8 H8 110.4 . . ? N1 C8 C7 104.41(18) . . ? N1 C8 H8 110.4 . . ? C7 C8 H8 110.4 . . ? O1 C9 H9A 110.9 . . ? O1 C9 H9B 110.9 . . ? O1 C9 C10 104.35(19) . . ? H9A C9 H9B 108.9 . . ? C10 C9 H9A 110.9 . . ? C10 C9 H9B 110.9 . . ? C7 C10 H10A 111.4 . . ? C7 C10 H10B 111.4 . . ? C9 C10 C7 101.8(2) . . ? C9 C10 H10A 111.4 . . ? C9 C10 H10B 111.4 . . ? H10A C10 H10B 109.3 . . ? C12 C11 S1 119.69(18) . . ? C16 C11 S1 119.49(17) . . ? C16 C11 C12 120.8(2) . . ? C11 C12 H12 120.5 . . ? C13 C12 C11 119.0(2) . . ? C13 C12 H12 120.5 . . ? C12 C13 H13 119.1 . . ? C12 C13 C14 121.8(2) . . ? C14 C13 H13 119.1 . . ? C13 C14 C15 117.8(2) . . ? C13 C14 C17 120.7(2) . . ? C15 C14 C17 121.6(2) . . ? C14 C15 H15 119.1 . . ? C16 C15 C14 121.8(2) . . ? C16 C15 H15 119.1 . . ? C11 C16 H16 120.6 . . ? C15 C16 C11 118.9(2) . . ? C15 C16 H16 120.6 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O5 S2 O6 119.90(11) . . ? O5 S2 N2 105.83(10) . . ? O5 S2 C28 108.78(11) . . ? O6 S2 N2 107.25(10) . . ? O6 S2 C28 107.20(10) . . ? N2 S2 C28 107.28(10) . . ? C27 O4 C26 106.8(2) . . ? C18 N2 S2 125.75(16) . . ? C18 N2 C27 111.46(18) . . ? C27 N2 S2 121.84(16) . . ? C19 C18 N2 129.0(2) . . ? C19 C18 C23 122.1(2) . . ? C23 C18 N2 108.85(19) . . ? C18 C19 H19 121.3 . . ? C18 C19 C20 117.3(2) . . ? C20 C19 H19 121.3 . . ? C19 C20 H20 119.2 . . ? C21 C20 C19 121.6(2) . . ? C21 C20 H20 119.2 . . ? C20 C21 H21 120.1 . . ? C22 C21 C20 119.8(2) . . ? C22 C21 H21 120.1 . . ? C21 C22 H22 120.2 . . ? C23 C22 C21 119.6(2) . . ? C23 C22 H22 120.2 . . ? C18 C23 C24 110.8(2) . . ? C22 C23 C18 119.5(2) . . ? C22 C23 C24 129.6(2) . . ? C23 C24 H24 112.2 . . ? C23 C24 C25 112.4(2) . . ? C23 C24 C27 104.98(18) . . ? C25 C24 H24 112.2 . . ? C25 C24 C27 102.1(2) . . ? C27 C24 H24 112.2 . . ? C24 C25 H25A 111.2 . . ? C24 C25 H25B 111.2 . . ? H25A C25 H25B 109.1 . . ? C26 C25 C24 102.8(2) . . ? C26 C25 H25A 111.2 . . ? C26 C25 H25B 111.2 . . ? O4 C26 C25 103.3(3) . . ? O4 C26 H26A 111.1 . . ? O4 C26 H26B 111.1 . . ? C25 C26 H26A 111.1 . . ? C25 C26 H26B 111.1 . . ? H26A C26 H26B 109.1 . . ? O4 C27 N2 112.85(18) . . ? O4 C27 C24 107.4(2) . . ? O4 C27 H27 110.9 . . ? N2 C27 C24 103.64(18) . . ? N2 C27 H27 110.9 . . ? C24 C27 H27 110.9 . . ? C29 C28 S2 119.25(18) . . ? C33 C28 S2 120.00(18) . . ? C33 C28 C29 120.7(2) . . ? C28 C29 H29 120.6 . . ? C30 C29 C28 118.9(2) . . ? C30 C29 H29 120.6 . . ? C29 C30 H30 119.2 . . ? C29 C30 C31 121.6(2) . . ? C31 C30 H30 119.2 . . ? C30 C31 C32 118.2(2) . . ? C30 C31 C34 121.3(2) . . ? C32 C31 C34 120.4(2) . . ? C31 C32 H32 119.3 . . ? C33 C32 C31 121.3(2) . . ? C33 C32 H32 119.3 . . ? C28 C33 H33 120.4 . . ? C32 C33 C28 119.2(2) . . ? C32 C33 H33 120.4 . . ? C31 C34 H34A 109.5 . . ? C31 C34 H34B 109.5 . . ? C31 C34 H34C 109.5 . . ? H34A C34 H34B 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? _shelx_res_file ; TITL exp_815_a.res in P2(1)2(1)2(1) exp_815.res created by SHELXL-2016/6 at 15:15:55 on 13-May-2019 REM Old TITL exp_815 in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.074, Rweak 0.033, Alpha 0.003, Orientation as input REM Flack x = 0.027 ( 0.005 ) from Parsons' quotients REM Formula found by SHELXT: C34 N3 O5 S2 CELL 1.54184 8.9043 10.7948 31.6319 90 90 90 ZERR 4 0.0001 0.0001 0.0002 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O S UNIT 136 136 8 24 8 L.S. 64 PLAN 6 BOND $H list 4 fmap 2 53 ACTA OMIT 0 6 0 OMIT 2 0 9 OMIT -3 2 9 OMIT 0 1 13 OMIT 3 2 9 REM REM REM WGHT 0.038000 0.928300 FVAR 0.49949 S1 5 -0.295122 0.470377 0.536346 11.00000 0.02189 0.02348 = 0.02290 -0.00079 0.00254 0.00199 O1 4 0.036496 0.432883 0.498067 11.00000 0.02986 0.02412 = 0.03043 0.00014 0.00575 0.00576 O2 4 -0.314851 0.400198 0.498398 11.00000 0.02981 0.03159 = 0.02459 -0.00456 -0.00264 -0.00022 O3 4 -0.416731 0.542572 0.552905 11.00000 0.02451 0.02920 = 0.03201 0.00142 0.00540 0.00581 N1 3 -0.157461 0.566787 0.526083 11.00000 0.02617 0.02451 = 0.02138 -0.00283 0.00602 0.00041 C1 1 -0.104623 0.661102 0.553738 11.00000 0.02705 0.01906 = 0.01946 0.00222 0.00032 0.00454 C2 1 -0.165704 0.703005 0.591628 11.00000 0.03054 0.02356 = 0.02211 0.00237 0.00467 0.00431 AFIX 43 H2 2 -0.252092 0.667571 0.602889 11.00000 -1.20000 AFIX 0 C3 1 -0.092639 0.799793 0.611969 11.00000 0.03854 0.02294 = 0.02145 -0.00090 -0.00223 0.00631 AFIX 43 H3 2 -0.130350 0.828989 0.637512 11.00000 -1.20000 AFIX 0 C4 1 0.035518 0.854040 0.595045 11.00000 0.03362 0.02119 = 0.03049 -0.00109 -0.00756 0.00312 AFIX 43 H4 2 0.082175 0.918947 0.609232 11.00000 -1.20000 AFIX 0 C5 1 0.094431 0.811421 0.556825 11.00000 0.02661 0.02374 = 0.03180 0.00484 -0.00042 0.00117 AFIX 43 H5 2 0.179893 0.847655 0.545303 11.00000 -1.20000 AFIX 0 C6 1 0.023607 0.714426 0.536378 11.00000 0.02425 0.02174 = 0.02195 0.00494 0.00089 0.00447 C7 1 0.065138 0.652149 0.495230 11.00000 0.02724 0.02467 = 0.02087 0.00668 0.00386 0.00180 AFIX 13 H7 2 0.055621 0.708666 0.471133 11.00000 -1.20000 AFIX 0 C8 1 -0.046182 0.542668 0.492171 11.00000 0.02783 0.02673 = 0.01854 0.00062 0.00403 0.00625 AFIX 13 H8 2 -0.095522 0.542135 0.464478 11.00000 -1.20000 AFIX 0 C9 1 0.180403 0.464196 0.515760 11.00000 0.03223 0.03228 = 0.02416 0.00151 0.00196 0.01153 AFIX 23 H9A 2 0.255019 0.402244 0.508534 11.00000 -1.20000 H9B 2 0.174450 0.471000 0.546291 11.00000 -1.20000 AFIX 0 C10 1 0.218742 0.587779 0.496033 11.00000 0.02582 0.03543 = 0.02781 -0.00010 0.00537 0.00393 AFIX 23 H10A 2 0.258979 0.577675 0.467746 11.00000 -1.20000 H10B 2 0.290257 0.633324 0.513165 11.00000 -1.20000 AFIX 0 C11 1 -0.232877 0.370873 0.577013 11.00000 0.02519 0.02166 = 0.02216 -0.00073 0.00198 -0.00025 C12 1 -0.282378 0.389735 0.618369 11.00000 0.02533 0.02486 = 0.02668 -0.00442 0.00520 0.00158 AFIX 43 H12 2 -0.344664 0.456229 0.624855 11.00000 -1.20000 AFIX 0 C13 1 -0.237326 0.307924 0.649595 11.00000 0.03008 0.02934 = 0.02129 -0.00341 0.00256 -0.00090 AFIX 43 H13 2 -0.269202 0.320902 0.677240 11.00000 -1.20000 AFIX 0 C14 1 -0.145585 0.206732 0.640739 11.00000 0.02486 0.02259 = 0.02530 -0.00194 -0.00112 -0.00411 C15 1 -0.096076 0.191673 0.599118 11.00000 0.02616 0.02352 = 0.02793 -0.00109 0.00148 0.00329 AFIX 43 H15 2 -0.032824 0.125771 0.592670 11.00000 -1.20000 AFIX 0 C16 1 -0.138717 0.272325 0.567190 11.00000 0.02948 0.02281 = 0.02312 -0.00200 0.00548 0.00207 AFIX 43 H16 2 -0.104875 0.260672 0.539662 11.00000 -1.20000 AFIX 0 C17 1 -0.104113 0.116081 0.674905 11.00000 0.03411 0.03020 = 0.02571 0.00178 -0.00306 -0.00028 AFIX 137 H17A 2 -0.064903 0.160178 0.698838 11.00000 -1.50000 H17B 2 -0.029306 0.059886 0.664424 11.00000 -1.50000 H17C 2 -0.191657 0.070315 0.683262 11.00000 -1.50000 AFIX 0 S2 5 0.444657 0.892479 0.726962 11.00000 0.01374 0.02502 = 0.02219 -0.00026 -0.00305 -0.00179 O4 4 0.487984 0.691319 0.654446 11.00000 0.02760 0.03794 = 0.03252 -0.00212 0.00572 0.00973 O5 4 0.598331 0.855794 0.729835 11.00000 0.01351 0.03971 = 0.03736 0.00475 -0.00776 -0.00168 O6 4 0.371948 0.947893 0.762710 11.00000 0.02486 0.02807 = 0.02038 -0.00308 -0.00044 -0.00511 N2 3 0.351356 0.767163 0.715170 11.00000 0.01321 0.02092 = 0.02650 -0.00148 -0.00116 0.00218 C18 1 0.192517 0.753930 0.716315 11.00000 0.01439 0.02248 = 0.01816 0.00212 -0.00194 -0.00022 C19 1 0.085465 0.836194 0.731025 11.00000 0.01823 0.02581 = 0.02150 -0.00132 0.00088 0.00067 AFIX 43 H19 2 0.112187 0.913755 0.741379 11.00000 -1.20000 AFIX 0 C20 1 -0.063694 0.798258 0.729708 11.00000 0.01776 0.03569 = 0.02264 0.00289 0.00202 0.00260 AFIX 43 H20 2 -0.138096 0.851636 0.739400 11.00000 -1.20000 AFIX 0 C21 1 -0.104246 0.682466 0.714251 11.00000 0.01539 0.03773 = 0.02407 0.00854 -0.00097 -0.00657 AFIX 43 H21 2 -0.204672 0.658831 0.713849 11.00000 -1.20000 AFIX 0 C22 1 0.005515 0.602217 0.699420 11.00000 0.02608 0.02704 = 0.02593 0.00472 -0.00413 -0.00698 AFIX 43 H22 2 -0.021096 0.525078 0.688682 11.00000 -1.20000 AFIX 0 C23 1 0.154599 0.637604 0.700702 11.00000 0.02141 0.01872 = 0.02340 0.00156 -0.00157 -0.00088 C24 1 0.291904 0.570418 0.685087 11.00000 0.02572 0.02084 = 0.04637 -0.00816 -0.00359 0.00499 AFIX 13 H24 2 0.305400 0.490132 0.699041 11.00000 -1.20000 AFIX 0 C25 1 0.295566 0.559353 0.636412 11.00000 0.03228 0.07398 = 0.05831 -0.04520 0.00047 0.00897 AFIX 23 H25A 2 0.352357 0.487224 0.627530 11.00000 -1.20000 H25B 2 0.194903 0.554381 0.624813 11.00000 -1.20000 AFIX 0 C26 1 0.371917 0.676589 0.623274 11.00000 0.03490 0.07949 = 0.02797 -0.01593 0.00181 0.01906 AFIX 23 H26A 2 0.414174 0.669015 0.595128 11.00000 -1.20000 H26B 2 0.302717 0.745973 0.623779 11.00000 -1.20000 AFIX 0 C27 1 0.424069 0.659846 0.693834 11.00000 0.01902 0.02287 = 0.03141 0.00192 0.00036 0.00776 AFIX 13 H27 2 0.498764 0.621073 0.712344 11.00000 -1.20000 AFIX 0 C28 1 0.424491 0.995757 0.684172 11.00000 0.01511 0.02307 = 0.02394 -0.00153 -0.00209 -0.00252 C29 1 0.517752 0.983084 0.649121 11.00000 0.01822 0.02762 = 0.03034 -0.00281 0.00190 -0.00033 AFIX 43 H29 2 0.590298 0.921157 0.648252 11.00000 -1.20000 AFIX 0 C30 1 0.500645 1.064347 0.615530 11.00000 0.02728 0.03070 = 0.02376 -0.00247 0.00523 -0.00575 AFIX 43 H30 2 0.563643 1.057055 0.592213 11.00000 -1.20000 AFIX 0 C31 1 0.391783 1.156300 0.615868 11.00000 0.03291 0.02270 = 0.02496 -0.00147 -0.00401 -0.00996 C32 1 0.300595 1.167099 0.651460 11.00000 0.03053 0.02753 = 0.03351 0.00036 0.00084 0.00638 AFIX 43 H32 2 0.227055 1.228237 0.652194 11.00000 -1.20000 AFIX 0 C33 1 0.317247 1.088637 0.685766 11.00000 0.02617 0.02873 = 0.02713 -0.00063 0.00549 0.00173 AFIX 43 H33 2 0.257166 1.098162 0.709594 11.00000 -1.20000 AFIX 0 C34 1 0.370654 1.241672 0.578776 11.00000 0.05186 0.02312 = 0.02855 0.00128 -0.00520 -0.00970 AFIX 137 H34A 2 0.401023 1.323951 0.586495 11.00000 -1.50000 H34B 2 0.266773 1.242260 0.570657 11.00000 -1.50000 H34C 2 0.430677 1.213308 0.555498 11.00000 -1.50000 AFIX 0 HKLF 4 REM exp_815_a.res in P2(1)2(1)2(1) REM R1 = 0.0300 for 6061 Fo > 4sig(Fo) and 0.0306 for all 6165 data REM 399 parameters refined using 0 restraints END WGHT 0.0378 0.9298 REM Highest difference peak 0.180, deepest hole -0.356, 1-sigma level 0.045 Q1 1 0.4448 0.8967 0.7846 11.00000 0.05 0.18 Q2 1 0.2827 0.3588 0.4800 11.00000 0.05 0.14 Q3 1 0.5851 0.8792 0.6391 11.00000 0.05 0.14 Q4 1 -0.3402 0.2819 0.6808 11.00000 0.05 0.13 Q5 1 -0.3182 0.6925 0.5995 11.00000 0.05 0.13 Q6 1 -0.0979 0.5214 0.5962 11.00000 0.05 0.13 ; _shelx_res_checksum 92400 _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 6.536 _oxdiff_exptl_absorpt_empirical_full_min 0.306