# Electronic Supplementary Material (ESI) for RSC Advances. # This journal is © The Royal Society of Chemistry 2018 ####################################################################### # # 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_pym_zhy_006 _database_code_depnum_ccdc_archive 'CCDC 1534893' _audit_update_record ; 2017-02-27 deposited with the CCDC. 2018-01-22 downloaded from the CCDC. ; _audit_creation_date 2016-11-01 _audit_creation_method ; Olex2 1.2 (compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227) ; _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C27 H19 N O, C H4 O' _chemical_formula_sum 'C28 H23 N O2' _chemical_formula_weight 405.47 _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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 10.426(2) _cell_length_b 12.933(3) _cell_length_c 16.851(4) _cell_angle_alpha 90 _cell_angle_beta 100.581(3) _cell_angle_gamma 90 _cell_volume 2233.6(8) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9591 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.37 _cell_measurement_theta_min 2.46 _shelx_estimated_absorpt_T_max 0.995 _shelx_estimated_absorpt_T_min 0.975 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_special_details ? _exptl_crystal_colour 'light yellow' _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_meas . _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_F_000 856 _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.07 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_unetI/netI 0.0190 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 24211 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.348 _diffrn_reflns_theta_min 1.987 _diffrn_ambient_temperature 296.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source ? _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 3346 _reflns_number_total 4091 _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 'SAINT v8.27A (Bruker, 2012)' _computing_data_collection ? _computing_data_reduction 'SAINT v8.27A (Bruker, 2012)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _refine_diff_density_max 0.150 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.038 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 283 _refine_ls_number_reflns 4091 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0367 _refine_ls_restrained_S_all 1.045 _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^)+(0.0511P)^2^+0.4954P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0983 _refine_ls_wR_factor_ref 0.1073 _refine_special_details ? _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27) 2.b Idealised Me refined as rotating group: C28(H28A,H28B,H28C) 2.c Idealised tetrahedral OH refined as rotating group: O1(H1), O2(H2A) ; _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 0.26014(9) 0.53997(8) 0.23191(7) 0.0531(3) Uani 1 1 d . . . . . H1 H 0.2714 0.4828 0.2531 0.080 Uiso 1 1 calc GR . . . . O2 O 0.29374(13) 0.34464(9) 0.28261(8) 0.0688(3) Uani 1 1 d . . . . . H2A H 0.2852 0.3095 0.3218 0.103 Uiso 1 1 calc GR . . . . N1 N 0.74016(10) 0.72417(8) 0.08350(6) 0.0378(3) Uani 1 1 d . . . . . C1 C 0.84204(12) 0.74027(10) 0.04334(8) 0.0393(3) Uani 1 1 d . . . . . C2 C 0.90963(14) 0.83515(12) 0.05389(10) 0.0530(4) Uani 1 1 d . . . . . H2 H 0.8827 0.8866 0.0857 0.064 Uiso 1 1 calc R . . . . C3 C 1.01440(17) 0.85159(14) 0.01752(12) 0.0681(5) Uani 1 1 d . . . . . H3 H 1.0589 0.9142 0.0253 0.082 Uiso 1 1 calc R . . . . C4 C 1.05606(17) 0.77574(15) -0.03139(11) 0.0689(5) Uani 1 1 d . . . . . H4 H 1.1281 0.7880 -0.0554 0.083 Uiso 1 1 calc R . . . . C5 C 0.99157(16) 0.68438(14) -0.04390(10) 0.0594(4) Uani 1 1 d . . . . . H5 H 1.0191 0.6347 -0.0770 0.071 Uiso 1 1 calc R . . . . C6 C 0.88275(13) 0.66396(11) -0.00698(8) 0.0446(3) Uani 1 1 d . . . . . C7 C 0.81091(15) 0.57128(12) -0.01773(9) 0.0506(4) Uani 1 1 d . . . . . H7 H 0.8332 0.5199 -0.0513 0.061 Uiso 1 1 calc R . . . . C8 C 0.70918(14) 0.55708(11) 0.02100(8) 0.0475(3) Uani 1 1 d . . . . . H8 H 0.6607 0.4963 0.0136 0.057 Uiso 1 1 calc R . . . . C9 C 0.67729(12) 0.63534(10) 0.07272(7) 0.0379(3) Uani 1 1 d . . . . . C10 C 0.56971(12) 0.61623(10) 0.11870(7) 0.0367(3) Uani 1 1 d . . . . . C11 C 0.45348(12) 0.67465(10) 0.10512(7) 0.0371(3) Uani 1 1 d . . . . . C12 C 0.43009(12) 0.76559(10) 0.04962(8) 0.0408(3) Uani 1 1 d . . . . . C13 C 0.45424(15) 0.76370(12) -0.02881(9) 0.0515(4) Uani 1 1 d . . . . . H13 H 0.4915 0.7054 -0.0475 0.062 Uiso 1 1 calc R . . . . C14 C 0.42316(17) 0.84813(14) -0.07927(10) 0.0621(4) Uani 1 1 d . . . . . H14 H 0.4391 0.8457 -0.1318 0.075 Uiso 1 1 calc R . . . . C15 C 0.36923(16) 0.93519(13) -0.05265(11) 0.0628(5) Uani 1 1 d . . . . . H15 H 0.3488 0.9916 -0.0869 0.075 Uiso 1 1 calc R . . . . C16 C 0.34558(15) 0.93884(12) 0.02463(11) 0.0582(4) Uani 1 1 d . . . . . H16 H 0.3096 0.9980 0.0430 0.070 Uiso 1 1 calc R . . . . C17 C 0.37515(14) 0.85476(11) 0.07543(9) 0.0485(3) Uani 1 1 d . . . . . H17 H 0.3581 0.8578 0.1276 0.058 Uiso 1 1 calc R . . . . C18 C 0.35225(12) 0.64701(10) 0.14470(8) 0.0403(3) Uani 1 1 d . . . . . H18 H 0.2749 0.6846 0.1352 0.048 Uiso 1 1 calc R . . . . C19 C 0.36496(12) 0.56470(10) 0.19783(8) 0.0397(3) Uani 1 1 d . . . . . C20 C 0.48176(12) 0.51130(11) 0.21497(8) 0.0408(3) Uani 1 1 d . . . . . H20 H 0.4919 0.4586 0.2532 0.049 Uiso 1 1 calc R . . . . C21 C 0.58438(12) 0.53538(10) 0.17572(8) 0.0380(3) Uani 1 1 d . . . . . C22 C 0.70842(12) 0.47560(11) 0.19862(8) 0.0414(3) Uani 1 1 d . . . . . C23 C 0.82951(14) 0.52374(13) 0.21756(9) 0.0542(4) Uani 1 1 d . . . . . H23 H 0.8349 0.5954 0.2151 0.065 Uiso 1 1 calc R . . . . C24 C 0.94230(15) 0.46583(16) 0.24004(11) 0.0670(5) Uani 1 1 d . . . . . H24 H 1.0226 0.4990 0.2528 0.080 Uiso 1 1 calc R . . . . C25 C 0.93618(16) 0.35972(16) 0.24361(10) 0.0668(5) Uani 1 1 d . . . . . H25 H 1.0122 0.3212 0.2583 0.080 Uiso 1 1 calc R . . . . C26 C 0.81785(16) 0.31106(14) 0.22553(10) 0.0597(4) Uani 1 1 d . . . . . H26 H 0.8133 0.2393 0.2279 0.072 Uiso 1 1 calc R . . . . C27 C 0.70506(14) 0.36863(12) 0.20378(9) 0.0486(3) Uani 1 1 d . . . . . H27 H 0.6251 0.3348 0.1923 0.058 Uiso 1 1 calc R . . . . C28 C 0.3081(2) 0.27951(15) 0.21817(11) 0.0750(5) Uani 1 1 d . . . . . H28A H 0.3231 0.3206 0.1733 0.113 Uiso 1 1 calc GR . . . . H28B H 0.2302 0.2393 0.2024 0.113 Uiso 1 1 calc GR . . . . H28C H 0.3809 0.2341 0.2347 0.113 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 O1 0.0399(5) 0.0585(6) 0.0660(7) 0.0159(5) 0.0237(5) 0.0019(5) O2 0.0807(8) 0.0618(7) 0.0702(8) 0.0270(6) 0.0306(6) 0.0083(6) N1 0.0357(6) 0.0417(6) 0.0371(6) -0.0019(5) 0.0094(4) -0.0044(5) C1 0.0343(6) 0.0470(8) 0.0369(7) 0.0019(6) 0.0076(5) -0.0039(5) C2 0.0477(8) 0.0485(8) 0.0650(10) -0.0012(7) 0.0164(7) -0.0088(7) C3 0.0541(10) 0.0659(11) 0.0887(13) 0.0050(9) 0.0248(9) -0.0197(8) C4 0.0525(10) 0.0871(13) 0.0749(11) 0.0040(10) 0.0323(8) -0.0128(9) C5 0.0528(9) 0.0768(11) 0.0543(9) -0.0044(8) 0.0252(7) -0.0026(8) C6 0.0424(7) 0.0560(9) 0.0369(7) -0.0012(6) 0.0111(6) -0.0023(6) C7 0.0554(9) 0.0550(9) 0.0444(8) -0.0134(7) 0.0174(7) -0.0034(7) C8 0.0525(8) 0.0463(8) 0.0463(8) -0.0111(6) 0.0159(6) -0.0120(6) C9 0.0366(7) 0.0425(7) 0.0347(7) -0.0018(5) 0.0065(5) -0.0062(5) C10 0.0353(6) 0.0406(7) 0.0342(6) -0.0045(5) 0.0068(5) -0.0080(5) C11 0.0368(7) 0.0398(7) 0.0339(6) -0.0037(5) 0.0045(5) -0.0072(5) C12 0.0347(7) 0.0451(8) 0.0412(7) 0.0021(6) 0.0033(5) -0.0084(5) C13 0.0562(9) 0.0560(9) 0.0418(8) 0.0043(7) 0.0077(6) -0.0040(7) C14 0.0689(11) 0.0699(11) 0.0461(9) 0.0138(8) 0.0068(8) -0.0099(9) C15 0.0611(10) 0.0551(10) 0.0675(11) 0.0213(8) -0.0004(8) -0.0105(8) C16 0.0515(9) 0.0446(8) 0.0761(11) 0.0059(8) 0.0055(8) -0.0047(7) C17 0.0447(8) 0.0482(8) 0.0521(8) 0.0003(7) 0.0075(6) -0.0068(6) C18 0.0341(6) 0.0440(7) 0.0425(7) -0.0007(6) 0.0065(5) -0.0020(5) C19 0.0343(6) 0.0456(7) 0.0408(7) -0.0004(6) 0.0110(5) -0.0062(6) C20 0.0376(7) 0.0453(7) 0.0397(7) 0.0059(6) 0.0073(5) -0.0041(6) C21 0.0326(6) 0.0437(7) 0.0375(7) -0.0029(5) 0.0059(5) -0.0063(5) C22 0.0361(7) 0.0527(8) 0.0366(7) 0.0003(6) 0.0095(5) -0.0009(6) C23 0.0379(7) 0.0645(10) 0.0596(9) 0.0013(7) 0.0073(7) -0.0043(7) C24 0.0334(8) 0.0968(14) 0.0698(11) 0.0009(10) 0.0065(7) -0.0007(8) C25 0.0508(10) 0.0898(14) 0.0616(10) 0.0087(9) 0.0153(8) 0.0245(9) C26 0.0615(10) 0.0635(10) 0.0578(9) 0.0058(8) 0.0204(8) 0.0159(8) C27 0.0457(8) 0.0539(9) 0.0477(8) 0.0011(7) 0.0122(6) 0.0001(6) C28 0.0881(13) 0.0755(12) 0.0595(10) 0.0169(9) 0.0085(9) -0.0105(10) _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 0.8200 . ? O1 C19 1.3627(15) . ? O2 H2A 0.8200 . ? O2 C28 1.404(2) . ? N1 C1 1.3762(16) . ? N1 C9 1.3186(16) . ? C1 C2 1.4099(19) . ? C1 C6 1.4160(19) . ? C2 H2 0.9300 . ? C2 C3 1.364(2) . ? C3 H3 0.9300 . ? C3 C4 1.401(3) . ? C4 H4 0.9300 . ? C4 C5 1.357(2) . ? C5 H5 0.9300 . ? C5 C6 1.415(2) . ? C6 C7 1.408(2) . ? C7 H7 0.9300 . ? C7 C8 1.356(2) . ? C8 H8 0.9300 . ? C8 C9 1.4145(19) . ? C9 C10 1.4962(17) . ? C10 C11 1.4107(18) . ? C10 C21 1.4093(18) . ? C11 C12 1.4947(18) . ? C11 C18 1.3946(18) . ? C12 C13 1.390(2) . ? C12 C17 1.392(2) . ? C13 H13 0.9300 . ? C13 C14 1.385(2) . ? C14 H14 0.9300 . ? C14 C15 1.370(3) . ? C15 H15 0.9300 . ? C15 C16 1.370(3) . ? C16 H16 0.9300 . ? C16 C17 1.383(2) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C18 C19 1.3816(19) . ? C19 C20 1.3835(19) . ? C20 H20 0.9300 . ? C20 C21 1.3925(18) . ? C21 C22 1.4953(18) . ? C22 C23 1.3912(19) . ? C22 C27 1.387(2) . ? C23 H23 0.9300 . ? C23 C24 1.387(2) . ? C24 H24 0.9300 . ? C24 C25 1.376(3) . ? C25 H25 0.9300 . ? C25 C26 1.369(3) . ? C26 H26 0.9300 . ? C26 C27 1.383(2) . ? C27 H27 0.9300 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 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 C19 O1 H1 109.5 . . ? C28 O2 H2A 109.5 . . ? C9 N1 C1 118.24(11) . . ? N1 C1 C2 118.86(12) . . ? N1 C1 C6 122.16(12) . . ? C2 C1 C6 118.96(12) . . ? C1 C2 H2 119.9 . . ? C3 C2 C1 120.14(15) . . ? C3 C2 H2 119.9 . . ? C2 C3 H3 119.5 . . ? C2 C3 C4 121.05(16) . . ? C4 C3 H3 119.5 . . ? C3 C4 H4 119.9 . . ? C5 C4 C3 120.20(15) . . ? C5 C4 H4 119.9 . . ? C4 C5 H5 119.7 . . ? C4 C5 C6 120.57(15) . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 119.06(13) . . ? C7 C6 C1 117.37(12) . . ? C7 C6 C5 123.57(14) . . ? C6 C7 H7 120.1 . . ? C8 C7 C6 119.88(13) . . ? C8 C7 H7 120.1 . . ? C7 C8 H8 120.2 . . ? C7 C8 C9 119.52(13) . . ? C9 C8 H8 120.2 . . ? N1 C9 C8 122.76(12) . . ? N1 C9 C10 118.26(11) . . ? C8 C9 C10 118.96(11) . . ? C11 C10 C9 122.07(11) . . ? C21 C10 C9 118.55(11) . . ? C21 C10 C11 119.37(11) . . ? C10 C11 C12 124.03(11) . . ? C18 C11 C10 119.22(12) . . ? C18 C11 C12 116.75(12) . . ? C13 C12 C11 122.95(13) . . ? C13 C12 C17 117.92(13) . . ? C17 C12 C11 119.05(12) . . ? C12 C13 H13 119.8 . . ? C14 C13 C12 120.46(15) . . ? C14 C13 H13 119.8 . . ? C13 C14 H14 119.7 . . ? C15 C14 C13 120.70(16) . . ? C15 C14 H14 119.7 . . ? C14 C15 H15 120.1 . . ? C14 C15 C16 119.72(15) . . ? C16 C15 H15 120.1 . . ? C15 C16 H16 119.9 . . ? C15 C16 C17 120.17(16) . . ? C17 C16 H16 119.9 . . ? C12 C17 H17 119.5 . . ? C16 C17 C12 121.04(15) . . ? C16 C17 H17 119.5 . . ? C11 C18 H18 119.5 . . ? C19 C18 C11 121.09(12) . . ? C19 C18 H18 119.5 . . ? O1 C19 C18 117.71(12) . . ? O1 C19 C20 122.55(12) . . ? C18 C19 C20 119.73(12) . . ? C19 C20 H20 119.6 . . ? C19 C20 C21 120.85(12) . . ? C21 C20 H20 119.6 . . ? C10 C21 C22 122.68(11) . . ? C20 C21 C10 119.55(12) . . ? C20 C21 C22 117.73(12) . . ? C23 C22 C21 122.23(13) . . ? C27 C22 C21 120.09(12) . . ? C27 C22 C23 117.66(13) . . ? C22 C23 H23 119.7 . . ? C24 C23 C22 120.61(16) . . ? C24 C23 H23 119.7 . . ? C23 C24 H24 119.8 . . ? C25 C24 C23 120.45(16) . . ? C25 C24 H24 119.8 . . ? C24 C25 H25 120.1 . . ? C26 C25 C24 119.75(15) . . ? C26 C25 H25 120.1 . . ? C25 C26 H26 120.0 . . ? C25 C26 C27 119.95(17) . . ? C27 C26 H26 120.0 . . ? C22 C27 H27 119.2 . . ? C26 C27 C22 121.56(15) . . ? C26 C27 H27 119.2 . . ? O2 C28 H28A 109.5 . . ? O2 C28 H28B 109.5 . . ? O2 C28 H28C 109.5 . . ? H28A C28 H28B 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 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 O1 C19 C20 C21 176.58(12) . . . . ? N1 C1 C2 C3 177.27(15) . . . . ? N1 C1 C6 C5 -177.54(13) . . . . ? N1 C1 C6 C7 2.8(2) . . . . ? N1 C9 C10 C11 65.87(16) . . . . ? N1 C9 C10 C21 -115.85(14) . . . . ? C1 N1 C9 C8 -0.86(19) . . . . ? C1 N1 C9 C10 177.79(11) . . . . ? C1 C2 C3 C4 0.7(3) . . . . ? C1 C6 C7 C8 -1.5(2) . . . . ? C2 C1 C6 C5 1.2(2) . . . . ? C2 C1 C6 C7 -178.41(13) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? C3 C4 C5 C6 -0.8(3) . . . . ? C4 C5 C6 C1 0.0(2) . . . . ? C4 C5 C6 C7 179.57(16) . . . . ? C5 C6 C7 C8 178.84(15) . . . . ? C6 C1 C2 C3 -1.5(2) . . . . ? C6 C7 C8 C9 -0.8(2) . . . . ? C7 C8 C9 N1 2.1(2) . . . . ? C7 C8 C9 C10 -176.55(13) . . . . ? C8 C9 C10 C11 -115.43(14) . . . . ? C8 C9 C10 C21 62.86(16) . . . . ? C9 N1 C1 C2 179.60(12) . . . . ? C9 N1 C1 C6 -1.63(19) . . . . ? C9 C10 C11 C12 -5.21(18) . . . . ? C9 C10 C11 C18 174.28(11) . . . . ? C9 C10 C21 C20 -175.36(11) . . . . ? C9 C10 C21 C22 6.85(18) . . . . ? C10 C11 C12 C13 48.63(19) . . . . ? C10 C11 C12 C17 -134.92(13) . . . . ? C10 C11 C18 C19 1.12(19) . . . . ? C10 C21 C22 C23 47.25(19) . . . . ? C10 C21 C22 C27 -134.60(14) . . . . ? C11 C10 C21 C20 2.97(18) . . . . ? C11 C10 C21 C22 -174.81(12) . . . . ? C11 C12 C13 C14 175.97(13) . . . . ? C11 C12 C17 C16 -176.65(12) . . . . ? C11 C18 C19 O1 -177.61(12) . . . . ? C11 C18 C19 C20 2.8(2) . . . . ? C12 C11 C18 C19 -179.36(12) . . . . ? C12 C13 C14 C15 0.6(2) . . . . ? C13 C12 C17 C16 0.0(2) . . . . ? C13 C14 C15 C16 -0.1(3) . . . . ? C14 C15 C16 C17 -0.5(2) . . . . ? C15 C16 C17 C12 0.5(2) . . . . ? C17 C12 C13 C14 -0.5(2) . . . . ? C18 C11 C12 C13 -130.87(14) . . . . ? C18 C11 C12 C17 45.58(17) . . . . ? C18 C19 C20 C21 -3.9(2) . . . . ? C19 C20 C21 C10 0.97(19) . . . . ? C19 C20 C21 C22 178.86(12) . . . . ? C20 C21 C22 C23 -130.57(14) . . . . ? C20 C21 C22 C27 47.58(18) . . . . ? C21 C10 C11 C12 176.52(12) . . . . ? C21 C10 C11 C18 -3.99(18) . . . . ? C21 C22 C23 C24 178.76(14) . . . . ? C21 C22 C27 C26 -179.38(13) . . . . ? C22 C23 C24 C25 0.3(3) . . . . ? C23 C22 C27 C26 -1.1(2) . . . . ? C23 C24 C25 C26 -0.6(3) . . . . ? C24 C25 C26 C27 0.0(3) . . . . ? C25 C26 C27 C22 0.9(2) . . . . ? C27 C22 C23 C24 0.6(2) . . . . ? _shelx_SHELXL_version_number 2014/7 _iucr_refine_instructions_details ; pym_zhy_006.res created by SHELXL-2014/7 TITL PYM_ZHY_006 in P21/c #14 REM reset to P21/c #14 CELL 0.71073 10.4262 12.9335 16.8507 90 100.581 90 ZERR 4 0.0022 0.0028 0.0036 0 0.003 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 112 92 4 8 L.S. 50 PLAN 20 SIZE 0.34 0.18 0.07 TEMP 23 BOND $H HTAB 2 CONF MORE -1 fmap 2 acta SHEL 999 0.83 OMIT -3 0 6 OMIT -1 5 1 OMIT 4 7 0 REM REM REM WGHT 0.051100 0.495400 FVAR 0.15932 O1 4 0.260138 0.539968 0.231912 11.00000 0.03990 0.05854 = 0.06603 0.01591 0.02373 0.00188 AFIX 147 H1 2 0.271366 0.482782 0.253061 11.00000 -1.50000 AFIX 0 O2 4 0.293737 0.344638 0.282607 11.00000 0.08066 0.06176 = 0.07024 0.02702 0.03058 0.00827 AFIX 147 H2A 2 0.285163 0.309502 0.321802 11.00000 -1.50000 AFIX 0 N1 3 0.740163 0.724166 0.083503 11.00000 0.03572 0.04166 = 0.03713 -0.00195 0.00935 -0.00435 C1 1 0.842044 0.740268 0.043337 11.00000 0.03426 0.04703 = 0.03688 0.00193 0.00761 -0.00388 C2 1 0.909626 0.835146 0.053888 11.00000 0.04771 0.04854 = 0.06503 -0.00116 0.01642 -0.00875 AFIX 43 H2 2 0.882701 0.886621 0.085712 11.00000 -1.20000 AFIX 0 C3 1 1.014399 0.851589 0.017519 11.00000 0.05412 0.06595 = 0.08873 0.00495 0.02479 -0.01973 AFIX 43 H3 2 1.058887 0.914159 0.025318 11.00000 -1.20000 AFIX 0 C4 1 1.056062 0.775745 -0.031387 11.00000 0.05248 0.08712 = 0.07488 0.00402 0.03233 -0.01278 AFIX 43 H4 2 1.128149 0.788046 -0.055360 11.00000 -1.20000 AFIX 0 C5 1 0.991575 0.684381 -0.043897 11.00000 0.05282 0.07682 = 0.05435 -0.00439 0.02519 -0.00258 AFIX 43 H5 2 1.019112 0.634741 -0.077016 11.00000 -1.20000 AFIX 0 C6 1 0.882753 0.663965 -0.006977 11.00000 0.04239 0.05603 = 0.03689 -0.00118 0.01113 -0.00226 C7 1 0.810905 0.571276 -0.017729 11.00000 0.05542 0.05498 = 0.04442 -0.01343 0.01741 -0.00336 AFIX 43 H7 2 0.833162 0.519864 -0.051333 11.00000 -1.20000 AFIX 0 C8 1 0.709181 0.557083 0.021000 11.00000 0.05249 0.04635 = 0.04627 -0.01114 0.01588 -0.01197 AFIX 43 H8 2 0.660728 0.496336 0.013612 11.00000 -1.20000 AFIX 0 C9 1 0.677293 0.635338 0.072718 11.00000 0.03661 0.04250 = 0.03470 -0.00177 0.00651 -0.00617 C10 1 0.569714 0.616228 0.118700 11.00000 0.03527 0.04064 = 0.03424 -0.00454 0.00678 -0.00804 C11 1 0.453478 0.674646 0.105123 11.00000 0.03683 0.03977 = 0.03386 -0.00374 0.00455 -0.00719 C12 1 0.430086 0.765591 0.049615 11.00000 0.03471 0.04511 = 0.04120 0.00209 0.00332 -0.00837 C13 1 0.454238 0.763705 -0.028809 11.00000 0.05622 0.05597 = 0.04175 0.00426 0.00775 -0.00398 AFIX 43 H13 2 0.491515 0.705364 -0.047526 11.00000 -1.20000 AFIX 0 C14 1 0.423162 0.848127 -0.079271 11.00000 0.06893 0.06993 = 0.04613 0.01377 0.00679 -0.00988 AFIX 43 H14 2 0.439070 0.845692 -0.131767 11.00000 -1.20000 AFIX 0 C15 1 0.369226 0.935191 -0.052653 11.00000 0.06106 0.05514 = 0.06749 0.02132 -0.00043 -0.01054 AFIX 43 H15 2 0.348761 0.991556 -0.086907 11.00000 -1.20000 AFIX 0 C16 1 0.345582 0.938840 0.024634 11.00000 0.05154 0.04458 = 0.07606 0.00593 0.00549 -0.00469 AFIX 43 H16 2 0.309556 0.998000 0.042993 11.00000 -1.20000 AFIX 0 C17 1 0.375155 0.854763 0.075429 11.00000 0.04473 0.04818 = 0.05209 0.00034 0.00746 -0.00676 AFIX 43 H17 2 0.358081 0.857839 0.127642 11.00000 -1.20000 AFIX 0 C18 1 0.352254 0.647009 0.144698 11.00000 0.03415 0.04396 = 0.04254 -0.00070 0.00652 -0.00198 AFIX 43 H18 2 0.274913 0.684604 0.135165 11.00000 -1.20000 AFIX 0 C19 1 0.364961 0.564702 0.197833 11.00000 0.03430 0.04559 = 0.04077 -0.00036 0.01099 -0.00620 C20 1 0.481757 0.511299 0.214972 11.00000 0.03758 0.04533 = 0.03971 0.00594 0.00731 -0.00411 AFIX 43 H20 2 0.491861 0.458644 0.253199 11.00000 -1.20000 AFIX 0 C21 1 0.584376 0.535378 0.175719 11.00000 0.03264 0.04370 = 0.03747 -0.00292 0.00593 -0.00627 C22 1 0.708417 0.475597 0.198616 11.00000 0.03608 0.05271 = 0.03663 0.00032 0.00955 -0.00093 C23 1 0.829509 0.523736 0.217562 11.00000 0.03795 0.06449 = 0.05961 0.00126 0.00726 -0.00434 AFIX 43 H23 2 0.834876 0.595407 0.215133 11.00000 -1.20000 AFIX 0 C24 1 0.942301 0.465830 0.240039 11.00000 0.03340 0.09676 = 0.06978 0.00095 0.00650 -0.00074 AFIX 43 H24 2 1.022616 0.498962 0.252783 11.00000 -1.20000 AFIX 0 C25 1 0.936178 0.359721 0.243609 11.00000 0.05085 0.08981 = 0.06159 0.00872 0.01535 0.02452 AFIX 43 H25 2 1.012162 0.321203 0.258253 11.00000 -1.20000 AFIX 0 C26 1 0.817854 0.311059 0.225532 11.00000 0.06149 0.06350 = 0.05779 0.00577 0.02043 0.01594 AFIX 43 H26 2 0.813282 0.239340 0.227870 11.00000 -1.20000 AFIX 0 C27 1 0.705057 0.368629 0.203777 11.00000 0.04567 0.05389 = 0.04773 0.00106 0.01224 0.00014 AFIX 43 H27 2 0.625071 0.334810 0.192341 11.00000 -1.20000 AFIX 0 C28 1 0.308105 0.279507 0.218172 11.00000 0.08808 0.07549 = 0.05949 0.01693 0.00845 -0.01053 AFIX 137 H28A 2 0.323057 0.320559 0.173286 11.00000 -1.50000 H28B 2 0.230159 0.239334 0.202430 11.00000 -1.50000 H28C 2 0.380924 0.234087 0.234736 11.00000 -1.50000 AFIX 0 HKLF 4 REM PYM_ZHY_006 in P21/c #14 REM R1 = 0.0367 for 3346 Fo > 4sig(Fo) and 0.0473 for all 4091 data REM 283 parameters refined using 0 restraints END WGHT 0.0494 0.4709 REM Instructions for potential hydrogen bonds HTAB O1 O2 EQIV $1 -x+1, y-1/2, -z+1/2 HTAB O2 N1_$1 HTAB C20 O2 REM Highest difference peak 0.150, deepest hole -0.165, 1-sigma level 0.038 Q1 1 0.7215 0.7743 0.1117 11.00000 0.05 0.15 Q2 1 0.5158 0.6613 0.1230 11.00000 0.05 0.15 Q3 1 0.4215 0.6894 0.1427 11.00000 0.05 0.12 Q4 1 0.3958 0.6369 0.1057 11.00000 0.05 0.12 Q5 1 0.5924 0.6003 0.1645 11.00000 0.05 0.12 Q6 1 0.3442 0.5812 0.1475 11.00000 0.05 0.12 Q7 1 0.5799 0.5793 0.1496 11.00000 0.05 0.11 Q8 1 0.5672 0.5588 0.1294 11.00000 0.05 0.11 Q9 1 0.3155 0.1983 0.2296 11.00000 0.05 0.11 Q10 1 0.9021 0.7670 0.0713 11.00000 0.05 0.11 Q11 1 0.4472 0.8197 0.0713 11.00000 0.05 0.11 Q12 1 0.6459 0.5044 0.1787 11.00000 0.05 0.11 Q13 1 0.7587 0.5036 0.2354 11.00000 0.05 0.11 Q14 1 0.2118 0.3006 0.1650 11.00000 0.05 0.10 Q15 1 0.4614 0.6623 -0.0570 11.00000 0.05 0.10 Q16 1 0.5209 0.5027 0.1748 11.00000 0.05 0.10 Q17 1 0.6011 0.3151 0.1483 11.00000 0.05 0.09 Q18 1 0.4377 0.7183 0.0761 11.00000 0.05 0.09 Q19 1 0.4160 0.3455 0.4128 11.00000 0.05 0.09 Q20 1 0.3797 1.0230 0.1009 11.00000 0.05 0.09 REM The information below was added by Olex2. REM REM R1 = 0.0367 for 3346 Fo > 4sig(Fo) and 0.0473 for all 27144 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.15, deepest hole -0.16 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0473 REM R1_gt = 0.0367 REM wR_ref = 0.1073 REM GOOF = 1.045 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 27144 REM Reflections_gt = 3346 REM Parameters = n/a REM Hole = -0.16 REM Peak = 0.15 REM Flack = n/a ; _olex2_submission_special_instructions 'No special instructions were received'