# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'RSC Advances' _journal_coden_Cambridge 1500 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Krzysztof Wozniak' _publ_contact_author_email kwozniak@chem.uw.edu.pl _publ_section_title ; On differences in electron densities of phenoxazine and phenothiazine derivatives - charge density studies* ; _publ_author_name K.Wozniak # Attachment '- pao_xd.cif' data_PAO_3_H _database_code_depnum_ccdc_archive 'CCDC 852714' #TrackingRef '- pao_xd.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_melting_point 'not measured' _chemical_formula_moiety 'C20 H15 N1 O2' _chemical_formula_sum 'C20 H15 N1 O2' _chemical_formula_weight 301.33 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _space_group_IT_number 2 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z _cell_length_a 7.6407(3) _cell_length_b 9.6786(4) _cell_length_c 10.6854(4) _cell_angle_alpha 65.630(2) _cell_angle_beta 89.433(2) _cell_angle_gamma 89.894(2) _cell_volume 719.75(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 100 _cell_measurement_theta_min 2.09 _cell_measurement_theta_max 45.22 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description cuboid _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.09 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.985 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; R. H. Blessing, Acta Cryst., 1995, A51, 33-38 ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'rotating-anode X-ray source' _diffrn_radiation_source 'TXS rotating anode' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'multi-layer optics' _diffrn_radiation_probe X-ray _diffrn_detector 'APEXII CCD camera' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker APEXII' _diffrn_measurement_method 'omega scans' _diffrn_orient_matrix_type 'X-axis to radiation source' _diffrn_orient_matrix_UB_11 -0.684277E-1 _diffrn_orient_matrix_UB_12 0.780981E-1 _diffrn_orient_matrix_UB_13 -0.755751E-1 _diffrn_orient_matrix_UB_21 -0.534502E-1 _diffrn_orient_matrix_UB_22 0.353945E-1 _diffrn_orient_matrix_UB_23 0.673951E-1 _diffrn_orient_matrix_UB_31 0.979376E-1 _diffrn_orient_matrix_UB_32 0.742546E-1 _diffrn_orient_matrix_UB_33 -0.173978E-1 _diffrn_reflns_number 54754 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_theta_max 45.22 _diffrn_reflns_theta_min 2.514 _diffrn_reflns_av_r_equivalents 0.0221 _diffrn_measured_fraction_theta_max 0.96 _reflns_number_total 11500 _reflns_number_gt 8836 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R. H. Blessing, Cryst. Rev., 1987, 1, 3-58 R. H. Blessing, J. Appl. Cryst., 1989, 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 software' _computing_cell_refinement 'Bruker APEX2 software' _computing_data_reduction ; SAINT intergration software, Bruker AXS SORTAV, R. H. Blessing, Acta Cryst., 1995, A51, 33-38 ; _computing_structure_solution ; SHELXS-97, G. M. Sheldrick, Acta. Cryst., 2008, A64, 112-122 ; _computing_structure_refinement ; SHELXS-97, G. M. Sheldrick, Acta. Cryst., 2008, A64, 112-122 XD2006, A. Volkov et al., 2006 ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.021 _refine_ls_R_factor_all 0.044 _refine_ls_R_Fsqd_factor 0.032 _refine_ls_wR_factor_ref 0.046 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 10516 _refine_ls_number_parameters 714 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w2 = 1/[s^2^(Fo^2^)] ; _refine_ls_shift/su_max 0 _refine_ls_extinction_method none _refine_diff_density_max 0.197 _refine_diff_density_min -0.126 _refine_diff_density_rms 0.038 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_U_iso_or_equiv O(1) 1.65913(5) -0.17532(6) 0.41808(5) 1 2 0.026 O(13) 0.74981(7) 0.47828(4) 0.03967(4) 1 2 0.017 N(8) 0.98483(4) 0.24316(3) 0.18437(3) 1 2 0.016 C(1) 1.50604(4) -0.20062(3) 0.45437(3) 1 2 0.016 C(2) 1.36755(3) -0.08662(3) 0.38438(2) 1 2 0.013 C(3) 1.19028(3) -0.11905(3) 0.41605(3) 1 2 0.015 C(4) 1.06283(3) -0.01112(3) 0.35004(3) 1 2 0.015 C(5) 1.11327(3) 0.13072(3) 0.25126(2) 1 2 0.013 C(6) 1.29044(4) 0.16440(3) 0.21837(3) 1 2 0.015 C(7) 1.41678(3) 0.05599(3) 0.28432(3) 1 2 0.014 C(9) 0.85257(4) 0.09420(3) 0.07019(3) 1 2 0.015 C(10) 0.73094(4) 0.08315(3) -0.02176(3) 1 2 0.017 C(11) 0.61564(4) 0.20114(3) -0.08932(3) 1 2 0.017 C(12) 0.62390(4) 0.33172(3) -0.06482(3) 1 2 0.015 C(14) 0.84140(4) 0.61701(3) 0.16383(3) 1 2 0.016 C(15) 0.94388(4) 0.63435(3) 0.26371(3) 1 2 0.018 C(16) 1.05989(4) 0.51980(3) 0.33839(3) 1 2 0.018 C(17) 1.07408(4) 0.38922(3) 0.31411(3) 1 2 0.015 C(18) 0.97401(3) 0.37205(3) 0.21278(2) 1 2 0.012 C(19) 0.85620(3) 0.48758(3) 0.13940(2) 1 2 0.013 C(20) 0.86175(3) 0.22421(3) 0.09606(2) 1 2 0.012 C(21) 0.74557(3) 0.34270(3) 0.02592(2) 1 2 0.013 C(22) 1.45349(5) -0.34685(4) 0.57216(4) 1 2 0.025 H(22A) 1.563337 -0.4164 0.615768 1 2 0.046 H(22B) 1.369085 -0.411983 0.539585 1 2 0.043 H(22C) 1.38311 -0.325294 0.64808 1 2 0.042 H(17) 1.159612 0.29705 0.374895 1 2 0.029 H(9) 0.9417 0.001879 0.123681 1 2 0.029 H(4) 0.925629 -0.037813 0.374193 1 2 0.029 H(14) 0.747952 0.702394 0.103908 1 2 0.033 H(3) 1.148906 -0.228526 0.492643 1 2 0.032 H(6) 1.325727 0.276097 0.142404 1 2 0.028 H(7) 1.553715 0.08175 0.258077 1 2 0.031 H(12) 0.541045 0.429725 -0.115034 1 2 0.032 H(16) 1.13455 0.527778 0.420786 1 2 0.033 H(15) 0.919748 0.735894 0.280224 1 2 0.036 H(11) 0.52033 0.190162 -0.159031 1 2 0.034 H(10) 0.725494 -0.020264 -0.037653 1 2 0.033 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.012155 0.026726 0.027944 0.004542 0.000877 -0.000456 O(13) 0.020153 0.012715 0.020851 0.005117 -0.008405 -0.008653 N(8) 0.015319 0.012658 0.022193 0.004499 -0.007958 -0.009582 C(1) 0.01239 0.014872 0.017263 0.002158 -0.001912 -0.003926 C(2) 0.010748 0.0124 0.014495 0.001053 -0.000873 -0.004107 C(3) 0.011459 0.013127 0.01717 0.00022 0.000146 -0.003235 C(4) 0.010716 0.013829 0.018773 0.000665 -0.000202 -0.005043 C(5) 0.011606 0.011671 0.016671 0.001798 -0.002572 -0.005823 C(6) 0.012898 0.012142 0.016457 0.000255 -0.001126 -0.003431 C(7) 0.011102 0.013308 0.016234 0.000046 -0.00015 -0.00371 C(9) 0.014266 0.013238 0.02003 0.001185 -0.002552 -0.009051 C(10) 0.015722 0.016736 0.022453 0.000139 -0.002692 -0.011636 C(11) 0.015364 0.019462 0.020601 0.000725 -0.003872 -0.011242 C(12) 0.01353 0.016514 0.017064 0.001885 -0.003601 -0.007769 C(14) 0.016603 0.012365 0.019612 0.001255 -0.000849 -0.008179 C(15) 0.019734 0.016618 0.023163 0.0007 -0.001486 -0.012379 C(16) 0.017516 0.019016 0.020094 -0.000099 -0.001982 -0.011985 C(17) 0.014108 0.015427 0.016447 0.000193 -0.002292 -0.007937 C(18) 0.011684 0.011214 0.014766 0.00058 -0.001239 -0.005851 C(19) 0.012588 0.01088 0.014876 0.000887 -0.00097 -0.00566 C(20) 0.010854 0.011449 0.015768 0.000859 -0.001749 -0.006442 C(21) 0.011703 0.012027 0.014854 0.001352 -0.001831 -0.00604 C(22) 0.017751 0.016597 0.028587 0.000741 -0.003943 0.001427 H(22A) 0.026741 0.038197 0.05173 0.012043 -0.004278 0.001934 H(22B) 0.042659 0.03381 0.045558 -0.006476 -0.006089 -0.008962 H(22C) 0.043364 0.036806 0.038159 0.003027 0.009682 -0.008327 H(17) 0.028325 0.026034 0.031263 0.005798 -0.009386 -0.011376 H(9) 0.028858 0.022768 0.036957 0.008162 -0.009597 -0.013386 H(4) 0.016898 0.027711 0.036709 -0.00201 0.000802 -0.008946 H(14) 0.035426 0.025783 0.039904 0.011581 -0.010638 -0.015206 H(3) 0.027002 0.021549 0.035041 -0.001377 0.001032 -0.000493 H(6) 0.026107 0.020976 0.029812 -0.001904 0.000802 -0.002805 H(7) 0.016821 0.032616 0.036401 -0.000512 0.001974 -0.007004 H(12) 0.030762 0.028038 0.036805 0.010936 -0.012895 -0.013366 H(16) 0.036873 0.035591 0.033664 -0.000719 -0.009683 -0.021295 H(15) 0.044836 0.027064 0.044793 0.004788 -0.005473 -0.024499 H(11) 0.031972 0.038415 0.037416 0.00272 -0.015137 -0.021448 H(10) 0.03757 0.027067 0.042918 0.002049 -0.008544 -0.023105 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(1) 1.2216(5) 1_555 1_555 yes O(13) C(19) 1.3788(5) 1_555 1_555 yes O(13) C(21) 1.3798(4) 1_555 1_555 yes N(8) C(5) 1.4235(4) 1_555 1_555 yes N(8) C(18) 1.4024(3) 1_555 1_555 yes N(8) C(20) 1.4034(4) 1_555 1_555 yes C(1) C(2) 1.4923(3) 1_555 1_555 yes C(1) C(22) 1.5068(4) 1_555 1_555 yes C(2) C(3) 1.3974(3) 1_555 1_555 yes C(2) C(7) 1.4021(3) 1_555 1_555 yes C(3) C(4) 1.3924(4) 1_555 1_555 yes C(3) H(3) 1.0830(2) 1_555 1_555 yes C(4) C(5) 1.3948(3) 1_555 1_555 yes C(4) H(4) 1.0830(3) 1_555 1_555 yes C(5) C(6) 1.4000(4) 1_555 1_555 yes C(6) C(7) 1.3888(3) 1_555 1_555 yes C(6) H(6) 1.0830(2) 1_555 1_555 yes C(7) H(7) 1.0830(3) 1_555 1_555 yes C(9) C(10) 1.3948(4) 1_555 1_555 yes C(9) C(20) 1.3974(3) 1_555 1_555 yes C(9) H(9) 1.0830(3) 1_555 1_555 yes C(10) C(11) 1.3892(4) 1_555 1_555 yes C(10) H(10) 1.0830(3) 1_555 1_555 yes C(11) C(12) 1.3941(4) 1_555 1_555 yes C(11) H(11) 1.0830(3) 1_555 1_555 yes C(12) C(21) 1.3852(4) 1_555 1_555 yes C(12) H(12) 1.0830(3) 1_555 1_555 yes C(14) C(15) 1.3947(4) 1_555 1_555 yes C(14) C(19) 1.3852(3) 1_555 1_555 yes C(14) H(14) 1.0830(3) 1_555 1_555 yes C(15) C(16) 1.3900(4) 1_555 1_555 yes C(15) H(15) 1.0830(3) 1_555 1_555 yes C(16) C(17) 1.3949(4) 1_555 1_555 yes C(16) H(16) 1.0830(3) 1_555 1_555 yes C(17) C(18) 1.3963(4) 1_555 1_555 yes C(17) H(17) 1.0830(3) 1_555 1_555 yes C(18) C(19) 1.4008(3) 1_555 1_555 yes C(20) C(21) 1.4018(3) 1_555 1_555 yes C(22) H(22A) 1.0590(3) 1_555 1_555 yes C(22) H(22B) 1.0590(4) 1_555 1_555 yes C(22) H(22C) 1.0590(4) 1_555 1_555 yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(19) O(13) C(21) 117.79(3) 1_555 1_555 1_555 yes C(5) N(8) C(18) 119.58(2) 1_555 1_555 1_555 yes C(5) N(8) C(20) 121.45(2) 1_555 1_555 1_555 yes C(18) N(8) C(20) 118.87(2) 1_555 1_555 1_555 yes O(1) C(1) C(2) 120.76(3) 1_555 1_555 1_555 yes O(1) C(1) C(22) 120.63(3) 1_555 1_555 1_555 yes C(2) C(1) C(22) 118.61(2) 1_555 1_555 1_555 yes C(1) C(2) C(3) 121.48(2) 1_555 1_555 1_555 yes C(1) C(2) C(7) 119.12(2) 1_555 1_555 1_555 yes C(3) C(2) C(7) 119.39(2) 1_555 1_555 1_555 yes C(2) C(3) C(4) 120.71(2) 1_555 1_555 1_555 yes C(2) C(3) H(3) 120.79(2) 1_555 1_555 1_555 yes C(4) C(3) H(3) 118.50(2) 1_555 1_555 1_555 yes C(3) C(4) C(5) 119.44(2) 1_555 1_555 1_555 yes C(3) C(4) H(4) 120.20(2) 1_555 1_555 1_555 yes C(5) C(4) H(4) 120.35(2) 1_555 1_555 1_555 yes N(8) C(5) C(4) 120.15(3) 1_555 1_555 1_555 yes N(8) C(5) C(6) 119.47(2) 1_555 1_555 1_555 yes C(4) C(5) C(6) 120.37(2) 1_555 1_555 1_555 yes C(5) C(6) C(7) 119.86(2) 1_555 1_555 1_555 yes C(5) C(6) H(6) 118.68(2) 1_555 1_555 1_555 yes C(7) C(6) H(6) 121.45(2) 1_555 1_555 1_555 yes C(2) C(7) C(6) 120.22(2) 1_555 1_555 1_555 yes C(2) C(7) H(7) 119.97(2) 1_555 1_555 1_555 yes C(6) C(7) H(7) 119.81(2) 1_555 1_555 1_555 yes C(10) C(9) C(20) 120.84(2) 1_555 1_555 1_555 yes C(10) C(9) H(9) 120.75(2) 1_555 1_555 1_555 yes C(20) C(9) H(9) 118.41(2) 1_555 1_555 1_555 yes C(9) C(10) C(11) 120.66(2) 1_555 1_555 1_555 yes C(9) C(10) H(10) 118.88(3) 1_555 1_555 1_555 yes C(11) C(10) H(10) 120.44(3) 1_555 1_555 1_555 yes C(10) C(11) C(12) 119.07(3) 1_555 1_555 1_555 yes C(10) C(11) H(11) 119.85(3) 1_555 1_555 1_555 yes C(12) C(11) H(11) 121.07(3) 1_555 1_555 1_555 yes C(11) C(12) C(21) 120.12(2) 1_555 1_555 1_555 yes C(11) C(12) H(12) 123.70(3) 1_555 1_555 1_555 yes C(21) C(12) H(12) 116.16(2) 1_555 1_555 1_555 yes C(15) C(14) C(19) 120.23(3) 1_555 1_555 1_555 yes C(15) C(14) H(14) 121.79(2) 1_555 1_555 1_555 yes C(19) C(14) H(14) 117.98(3) 1_555 1_555 1_555 yes C(14) C(15) C(16) 119.03(2) 1_555 1_555 1_555 yes C(14) C(15) H(15) 115.69(3) 1_555 1_555 1_555 yes C(16) C(15) H(15) 125.18(3) 1_555 1_555 1_555 yes C(15) C(16) C(17) 120.67(3) 1_555 1_555 1_555 yes C(15) C(16) H(16) 120.17(2) 1_555 1_555 1_555 yes C(17) C(16) H(16) 119.05(3) 1_555 1_555 1_555 yes C(16) C(17) C(18) 120.65(2) 1_555 1_555 1_555 yes C(16) C(17) H(17) 121.25(3) 1_555 1_555 1_555 yes C(18) C(17) H(17) 118.07(2) 1_555 1_555 1_555 yes N(8) C(18) C(17) 122.56(2) 1_555 1_555 1_555 yes N(8) C(18) C(19) 119.37(2) 1_555 1_555 1_555 yes C(17) C(18) C(19) 118.05(2) 1_555 1_555 1_555 yes O(13) C(19) C(14) 116.84(3) 1_555 1_555 1_555 yes O(13) C(19) C(18) 121.82(3) 1_555 1_555 1_555 yes C(14) C(19) C(18) 121.34(2) 1_555 1_555 1_555 yes N(8) C(20) C(9) 123.21(2) 1_555 1_555 1_555 yes N(8) C(20) C(21) 119.06(2) 1_555 1_555 1_555 yes C(9) C(20) C(21) 117.69(2) 1_555 1_555 1_555 yes O(13) C(21) C(12) 116.32(3) 1_555 1_555 1_555 yes O(13) C(21) C(20) 122.04(3) 1_555 1_555 1_555 yes C(12) C(21) C(20) 121.61(2) 1_555 1_555 1_555 yes C(1) C(22) H(22A) 111.60(3) 1_555 1_555 1_555 yes C(1) C(22) H(22B) 111.49(3) 1_555 1_555 1_555 yes C(1) C(22) H(22C) 110.84(3) 1_555 1_555 1_555 yes H(22A) C(22) H(22B) 106.03(3) 1_555 1_555 1_555 yes H(22A) C(22) H(22C) 110.55(3) 1_555 1_555 1_555 yes H(22B) C(22) H(22C) 106.10(3) 1_555 1_555 1_555 yes 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 C(19) O(13) C(21) C(12) 173.36(5) 1_555 1_555 1_555 1_555 yes C(21) O(13) C(19) C(14) -171.74(5) 1_555 1_555 1_555 1_555 yes C(21) O(13) C(19) C(18) 8.31(3) 1_555 1_555 1_555 1_555 yes C(19) O(13) C(21) C(20) -8.77(3) 1_555 1_555 1_555 1_555 yes C(18) N(8) C(5) C(4) 110.15(4) 1_555 1_555 1_555 1_555 yes C(18) N(8) C(5) C(6) -69.02(3) 1_555 1_555 1_555 1_555 yes C(5) N(8) C(18) C(17) -6.00(2) 1_555 1_555 1_555 1_555 yes C(5) N(8) C(18) C(19) 175.35(4) 1_555 1_555 1_555 1_555 yes C(20) N(8) C(5) C(4) -66.23(3) 1_555 1_555 1_555 1_555 yes C(20) N(8) C(5) C(6) 114.60(4) 1_555 1_555 1_555 1_555 yes C(5) N(8) C(20) C(9) 1.78(2) 1_555 1_555 1_555 1_555 yes C(5) N(8) C(20) C(21) -175.87(4) 1_555 1_555 1_555 1_555 yes C(18) N(8) C(20) C(9) -174.62(4) 1_555 1_555 1_555 1_555 yes C(20) N(8) C(18) C(17) 170.47(4) 1_555 1_555 1_555 1_555 yes C(20) N(8) C(18) C(19) -8.18(2) 1_555 1_555 1_555 1_555 yes C(18) N(8) C(20) C(21) 7.73(2) 1_555 1_555 1_555 1_555 yes O(1) C(1) C(2) C(3) 174.10(5) 1_555 1_555 1_555 1_555 yes O(1) C(1) C(2) C(7) -5.70(3) 1_555 1_555 1_555 1_555 yes O(1) C(1) C(22) H(22A) 1.39(4) 1_555 1_555 1_555 1_555 yes O(1) C(1) C(22) H(22B) -116.97(5) 1_555 1_555 1_555 1_555 yes O(1) C(1) C(22) H(22C) 125.08(5) 1_555 1_555 1_555 1_555 yes C(22) C(1) C(2) C(3) -6.73(3) 1_555 1_555 1_555 1_555 yes C(22) C(1) C(2) C(7) 173.47(4) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(22) H(22A) -177.78(4) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(22) H(22B) 63.86(3) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(22) H(22C) -54.09(3) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(4) 179.78(4) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) H(3) -0.05(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(7) C(6) -179.57(4) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(7) H(7) 0.60(2) 1_555 1_555 1_555 1_555 yes C(7) C(2) C(3) C(4) -0.42(2) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(7) C(6) 0.63(2) 1_555 1_555 1_555 1_555 yes C(7) C(2) C(3) H(3) 179.75(4) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(7) H(7) -179.21(4) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) C(5) 0.03(2) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) H(4) 179.12(4) 1_555 1_555 1_555 1_555 yes H(3) C(3) C(4) C(5) 179.87(4) 1_555 1_555 1_555 1_555 yes H(3) C(3) C(4) H(4) -1.04(2) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(5) N(8) -179.01(4) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(5) C(6) 0.15(2) 1_555 1_555 1_555 1_555 yes H(4) C(4) C(5) N(8) 1.90(2) 1_555 1_555 1_555 1_555 yes H(4) C(4) C(5) C(6) -178.94(4) 1_555 1_555 1_555 1_555 yes N(8) C(5) C(6) C(7) 179.23(4) 1_555 1_555 1_555 1_555 yes N(8) C(5) C(6) H(6) 0.12(2) 1_555 1_555 1_555 1_555 yes C(4) C(5) C(6) C(7) 0.06(2) 1_555 1_555 1_555 1_555 yes C(4) C(5) C(6) H(6) -179.05(4) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(7) C(2) -0.45(2) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(7) H(7) 179.39(4) 1_555 1_555 1_555 1_555 yes H(6) C(6) C(7) C(2) 178.63(4) 1_555 1_555 1_555 1_555 yes H(6) C(6) C(7) H(7) -1.53(2) 1_555 1_555 1_555 1_555 yes C(10) C(9) C(20) N(8) -178.06(4) 1_555 1_555 1_555 1_555 yes C(20) C(9) C(10) C(11) -0.25(3) 1_555 1_555 1_555 1_555 yes C(10) C(9) C(20) C(21) -0.38(2) 1_555 1_555 1_555 1_555 yes C(20) C(9) C(10) H(10) -178.65(4) 1_555 1_555 1_555 1_555 yes H(9) C(9) C(10) C(11) 179.40(4) 1_555 1_555 1_555 1_555 yes H(9) C(9) C(10) H(10) 1.00(2) 1_555 1_555 1_555 1_555 yes H(9) C(9) C(20) N(8) 2.27(2) 1_555 1_555 1_555 1_555 yes H(9) C(9) C(20) C(21) 179.96(4) 1_555 1_555 1_555 1_555 yes C(9) C(10) C(11) C(12) 0.49(3) 1_555 1_555 1_555 1_555 yes C(9) C(10) C(11) H(11) -178.89(4) 1_555 1_555 1_555 1_555 yes H(10) C(10) C(11) C(12) 178.87(4) 1_555 1_555 1_555 1_555 yes H(10) C(10) C(11) H(11) -0.52(3) 1_555 1_555 1_555 1_555 yes C(10) C(11) C(12) C(21) -0.09(3) 1_555 1_555 1_555 1_555 yes C(10) C(11) C(12) H(12) 178.47(4) 1_555 1_555 1_555 1_555 yes H(11) C(11) C(12) C(21) 179.28(4) 1_555 1_555 1_555 1_555 yes H(11) C(11) C(12) H(12) -2.16(2) 1_555 1_555 1_555 1_555 yes C(11) C(12) C(21) O(13) 177.32(4) 1_555 1_555 1_555 1_555 yes C(11) C(12) C(21) C(20) -0.56(2) 1_555 1_555 1_555 1_555 yes H(12) C(12) C(21) O(13) -1.35(3) 1_555 1_555 1_555 1_555 yes H(12) C(12) C(21) C(20) -179.23(4) 1_555 1_555 1_555 1_555 yes C(15) C(14) C(19) O(13) 179.62(4) 1_555 1_555 1_555 1_555 yes C(19) C(14) C(15) C(16) -0.31(3) 1_555 1_555 1_555 1_555 yes C(15) C(14) C(19) C(18) -0.43(2) 1_555 1_555 1_555 1_555 yes C(19) C(14) C(15) H(15) -176.94(4) 1_555 1_555 1_555 1_555 yes H(14) C(14) C(15) C(16) 179.20(4) 1_555 1_555 1_555 1_555 yes H(14) C(14) C(15) H(15) 2.57(2) 1_555 1_555 1_555 1_555 yes H(14) C(14) C(19) O(13) 0.10(3) 1_555 1_555 1_555 1_555 yes H(14) C(14) C(19) C(18) -179.96(4) 1_555 1_555 1_555 1_555 yes C(14) C(15) C(16) C(17) 0.02(3) 1_555 1_555 1_555 1_555 yes C(14) C(15) C(16) H(16) -176.08(4) 1_555 1_555 1_555 1_555 yes H(15) C(15) C(16) C(17) 176.30(5) 1_555 1_555 1_555 1_555 yes H(15) C(15) C(16) H(16) 0.21(3) 1_555 1_555 1_555 1_555 yes C(15) C(16) C(17) C(18) 1.02(3) 1_555 1_555 1_555 1_555 yes C(15) C(16) C(17) H(17) -177.13(4) 1_555 1_555 1_555 1_555 yes H(16) C(16) C(17) C(18) 177.16(4) 1_555 1_555 1_555 1_555 yes H(16) C(16) C(17) H(17) -0.99(2) 1_555 1_555 1_555 1_555 yes C(16) C(17) C(18) N(8) 179.62(4) 1_555 1_555 1_555 1_555 yes C(16) C(17) C(18) C(19) -1.71(2) 1_555 1_555 1_555 1_555 yes H(17) C(17) C(18) N(8) -2.17(2) 1_555 1_555 1_555 1_555 yes H(17) C(17) C(18) C(19) 176.50(4) 1_555 1_555 1_555 1_555 yes N(8) C(18) C(19) O(13) 0.09(3) 1_555 1_555 1_555 1_555 yes N(8) C(18) C(19) C(14) -179.86(4) 1_555 1_555 1_555 1_555 yes C(17) C(18) C(19) O(13) -178.62(4) 1_555 1_555 1_555 1_555 yes C(17) C(18) C(19) C(14) 1.43(2) 1_555 1_555 1_555 1_555 yes N(8) C(20) C(21) O(13) 0.82(3) 1_555 1_555 1_555 1_555 yes N(8) C(20) C(21) C(12) 178.57(4) 1_555 1_555 1_555 1_555 yes C(9) C(20) C(21) O(13) -176.96(4) 1_555 1_555 1_555 1_555 yes C(9) C(20) C(21) C(12) 0.79(2) 1_555 1_555 1_555 1_555 yes loop_ _atom_rho_multipole_atom_label _atom_rho_multipole_coeff_Pv _atom_rho_multipole_coeff_P00 _atom_rho_multipole_coeff_P11 _atom_rho_multipole_coeff_P1-1 _atom_rho_multipole_coeff_P10 _atom_rho_multipole_coeff_P20 _atom_rho_multipole_coeff_P21 _atom_rho_multipole_coeff_P2-1 _atom_rho_multipole_coeff_P22 _atom_rho_multipole_coeff_P2-2 _atom_rho_multipole_coeff_P30 _atom_rho_multipole_coeff_P31 _atom_rho_multipole_coeff_P3-1 _atom_rho_multipole_coeff_P32 _atom_rho_multipole_coeff_P3-2 _atom_rho_multipole_coeff_P33 _atom_rho_multipole_coeff_P3-3 _atom_rho_multipole_coeff_P40 _atom_rho_multipole_coeff_P41 _atom_rho_multipole_coeff_P4-1 _atom_rho_multipole_coeff_P42 _atom_rho_multipole_coeff_P4-2 _atom_rho_multipole_coeff_P43 _atom_rho_multipole_coeff_P4-3 _atom_rho_multipole_coeff_P44 _atom_rho_multipole_coeff_P4-4 _atom_rho_multipole_kappa _atom_rho_multipole_kappa_prime0 _atom_rho_multipole_kappa_prime1 _atom_rho_multipole_kappa_prime2 _atom_rho_multipole_kappa_prime3 _atom_rho_multipole_kappa_prime4 _atom_rho_multipole_radial_slater_n0 _atom_rho_multipole_radial_slater_zeta0 _atom_rho_multipole_radial_slater_n1 _atom_rho_multipole_radial_slater_zeta1 _atom_rho_multipole_radial_slater_n2 _atom_rho_multipole_radial_slater_zeta2 _atom_rho_multipole_radial_slater_n3 _atom_rho_multipole_radial_slater_zeta3 _atom_rho_multipole_radial_slater_n4 _atom_rho_multipole_radial_slater_zeta4 O(1) 6.41(3) 0 -0.002(13) 0.027(10) -0.028(10) 0.010(7) 0.037(8) -0.010(6) -0.075(7) 0.004(7) -0.011(9) 0.004(8) -0.013(7) 0.082(8) 0.040(8) 0.005(8) 0.013(8) -0.006(10) -0.016(11) -0.005(9) 0.007(10) 0.002(10) -0.012(10) 0.009(10) -0.005(10) -0.017(9) 0.990(2) 1.01(5) 1.01391 1.01391 1.01391 1.01391 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 O(13) 6.34(3) 0 0.069(9) -0.076(7) -0.049(9) -0.021(5) 0.013(5) 0.003(4) 0.011(4) -0.009(4) 0.041(6) -0.046(6) 0.001(6) 0.061(6) 0.003(6) 0.039(6) 0.013(5) -0.004(8) -0.007(8) 0.001(7) -0.009(8) -0.003(8) -0.002(7) -0.002(7) 0.007(7) 0.019(7) 0.9936(17) 1.18(5) 1.179322 1.179322 1.179322 1.179322 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 N(8) 5.33(5) 0 -0.033(11) 0.000(12) 0.020(11) -0.015(7) -0.003(7) 0.002(7) 0.022(7) 0.006(7) 0.167(18) 0.021(9) -0.015(10) 0.147(15) 0.012(10) -0.018(9) -0.002(9) 0.022(12) -0.010(10) -0.004(12) -0.003(12) -0.014(13) 0.003(10) -0.014(11) 0.012(10) 0.013(10) 0.992(3) 0.95(4) 0.953134 0.953134 0.953134 0.953134 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 C(1) 4.02(3) 0 0.012(15) 0.030(19) 0.11(2) 0.254(14) 0.028(11) 0.042(12) -0.251(12) -0.009(11) 0.38(2) 0.037(15) 0.016(17) 0.270(15) 0.026(16) 0.004(13) -0.022(15) 0.01(2) 0.024(19) 0.01(2) -0.097(19) 0.03(2) -0.018(17) -0.004(19) 0.082(17) -0.005(16) 1.0238(13) 0.843(5) 0.843074 0.843074 0.843074 0.843074 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(2) 4.02(4) 0 0.022(16) 0.08(2) 0.04(2) 0.091(13) 0.024(12) 0.006(13) -0.175(11) 0.017(11) 0.310(19) 0.017(15) -0.022(18) 0.254(17) -0.021(16) 0.015(13) -0.003(14) 0.01(3) -0.013(18) 0.01(2) 0.00(2) -0.01(2) 0.005(18) 0.02(2) 0.035(16) -0.014(16) 1.0238(13) 0.843(5) 0.843074 0.843074 0.843074 0.843074 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(3) 4.08(4) 0 0.036(16) 0.00(2) -0.034(19) 0.129(13) 0.016(11) -0.005(13) -0.218(12) 0.023(12) 0.359(18) -0.026(14) -0.022(18) 0.206(16) -0.024(16) 0.011(15) 0.013(15) 0.13(2) -0.017(19) 0.01(3) 0.001(17) 0.001(19) -0.004(17) 0.008(19) 0.057(17) -0.004(16) 1.0238(13) 0.843(5) 0.843074 0.843074 0.843074 0.843074 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(4) 4.09(3) 0 -0.006(16) -0.03(2) -0.01(2) 0.087(13) -0.022(11) -0.010(13) -0.181(12) 0.005(12) 0.335(18) -0.029(15) 0.027(18) 0.182(16) -0.003(16) -0.018(14) 0.009(16) 0.06(2) 0.012(19) -0.03(3) 0.031(17) 0.018(18) 0.026(17) -0.014(19) 0.035(17) -0.033(17) 1.0238(13) 0.843(5) 0.843074 0.843074 0.843074 0.843074 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(5) 4.08(4) 0 -0.004(16) 0.10(2) 0.10(2) 0.139(13) -0.005(12) -0.044(13) -0.136(12) 0.009(11) 0.291(19) -0.006(15) 0.008(18) 0.271(17) 0.020(16) -0.001(14) 0.041(14) 0.02(2) -0.035(18) 0.01(2) -0.03(2) 0.03(2) -0.027(19) 0.01(2) 0.088(16) 0.011(16) 1.0238(13) 0.843(5) 0.843074 0.843074 0.843074 0.843074 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(6) 4.12(4) 0 0.025(16) -0.02(2) -0.030(19) 0.125(13) -0.015(11) -0.023(13) -0.179(12) -0.017(12) 0.346(18) 0.020(14) 0.025(17) 0.205(16) -0.007(16) -0.002(15) -0.022(16) 0.05(2) 0.002(18) 0.01(3) 0.011(17) 0.000(18) -0.018(17) 0.026(18) 0.057(16) 0.021(16) 1.0238(13) 0.843(5) 0.843074 0.843074 0.843074 0.843074 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(7) 4.02(3) 0 -0.019(16) -0.02(2) -0.03(2) 0.098(13) 0.031(11) -0.019(13) -0.205(12) -0.006(12) 0.370(18) 0.032(15) 0.037(18) 0.187(16) -0.001(16) -0.022(14) 0.014(15) 0.10(2) 0.041(19) 0.01(3) 0.007(17) 0.011(18) -0.022(16) -0.009(18) 0.032(17) 0.026(16) 1.0238(13) 0.843(5) 0.843074 0.843074 0.843074 0.843074 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(9) 4.04(4) 0 0.010(16) 0.02(2) 0.040(19) 0.104(14) -0.007(11) -0.003(13) -0.158(13) -0.035(12) 0.300(19) -0.019(15) -0.004(19) 0.169(16) -0.004(16) 0.004(16) 0.004(16) 0.09(2) -0.024(18) 0.04(3) 0.011(18) -0.005(19) 0.009(17) -0.008(19) 0.016(17) 0.008(17) 1.0238(13) 0.843(5) 0.843074 0.843074 0.843074 0.843074 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(10) 4.13(4) 0 0.047(17) -0.00(2) -0.03(2) 0.124(14) -0.035(11) -0.008(14) -0.186(13) -0.027(12) 0.36(2) -0.013(15) -0.025(19) 0.223(17) 0.019(17) -0.010(15) 0.016(16) 0.06(2) -0.070(19) 0.00(3) -0.038(18) -0.012(19) 0.015(18) 0.038(19) 0.060(17) -0.015(17) 1.0238(13) 0.843(5) 0.843074 0.843074 0.843074 0.843074 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(11) 4.12(4) 0 -0.011(16) 0.00(2) -0.03(2) 0.091(14) 0.030(11) 0.013(14) -0.181(13) -0.005(12) 0.39(2) 0.010(15) -0.022(19) 0.198(17) -0.015(17) -0.005(15) 0.003(17) 0.03(2) 0.01(2) -0.01(3) -0.043(18) 0.017(19) 0.016(17) -0.015(19) 0.047(17) -0.035(17) 1.0238(13) 0.843(5) 0.843074 0.843074 0.843074 0.843074 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(12) 4.04(4) 0 0.014(16) 0.02(2) 0.002(19) 0.113(14) 0.007(11) 0.005(13) -0.154(13) 0.018(12) 0.335(19) -0.006(15) -0.055(19) 0.192(16) 0.009(16) 0.004(15) -0.016(16) 0.11(2) 0.029(18) 0.07(3) 0.003(18) -0.014(19) -0.022(17) 0.020(19) -0.021(17) -0.011(17) 1.0238(13) 0.843(5) 0.843074 0.843074 0.843074 0.843074 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(14) 3.96(4) 0 0.006(16) -0.04(2) -0.01(2) 0.097(14) 0.006(11) 0.009(13) -0.169(13) 0.004(12) 0.335(19) -0.019(15) 0.010(19) 0.198(16) -0.004(16) 0.025(15) 0.011(16) 0.11(2) 0.018(18) -0.04(3) 0.038(18) 0.035(19) 0.011(17) 0.021(19) 0.045(17) -0.015(17) 1.0238(13) 0.843(5) 0.843074 0.843074 0.843074 0.843074 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(15) 4.14(4) 0 0.022(17) 0.07(2) -0.03(2) 0.098(14) 0.014(11) -0.001(14) -0.171(13) -0.009(13) 0.36(2) -0.033(16) 0.10(2) 0.238(17) -0.014(17) -0.040(16) 0.036(17) 0.07(2) 0.053(19) 0.07(3) -0.028(19) 0.042(19) 0.034(18) 0.02(2) 0.037(18) 0.007(17) 1.0238(13) 0.843(5) 0.843074 0.843074 0.843074 0.843074 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(16) 4.03(4) 0 0.005(17) -0.04(2) 0.02(2) 0.118(14) -0.019(11) 0.009(14) -0.188(13) -0.019(12) 0.339(19) 0.001(16) 0.014(19) 0.229(17) 0.002(17) 0.025(16) 0.016(17) 0.08(2) 0.034(19) -0.06(3) -0.001(18) 0.019(19) 0.031(17) -0.073(19) 0.065(18) 0.038(17) 1.0238(13) 0.843(5) 0.843074 0.843074 0.843074 0.843074 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(17) 4.05(4) 0 -0.069(16) -0.01(2) 0.01(2) 0.086(14) 0.020(11) -0.025(13) -0.178(12) -0.027(12) 0.314(19) 0.023(15) 0.060(19) 0.179(16) 0.006(16) 0.034(15) -0.001(16) 0.08(2) -0.035(18) -0.04(3) 0.020(18) 0.005(19) -0.067(17) -0.029(18) 0.043(17) 0.004(17) 1.0238(13) 0.843(5) 0.843074 0.843074 0.843074 0.843074 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(18) 3.99(4) 0 0.001(15) 0.11(2) 0.07(2) 0.138(13) -0.009(12) -0.042(13) -0.148(11) -0.009(11) 0.313(19) 0.012(15) -0.022(18) 0.284(17) -0.019(16) 0.026(13) 0.027(14) -0.04(2) -0.007(18) 0.06(3) -0.06(2) -0.03(2) 0.017(18) -0.01(2) 0.068(16) 0.038(16) 1.0238(13) 0.843(5) 0.843074 0.843074 0.843074 0.843074 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(19) 4.01(3) 0 0.010(15) 0.05(2) -0.137(19) -0.002(13) 0.005(11) -0.062(13) -0.209(12) 0.003(11) 0.435(18) 0.018(14) -0.060(18) 0.179(15) 0.006(16) 0.023(14) -0.014(14) 0.11(2) 0.013(17) 0.03(3) 0.008(19) 0.05(2) 0.003(16) 0.005(18) 0.083(17) -0.031(16) 1.0238(13) 0.843(5) 0.843074 0.843074 0.843074 0.843074 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(20) 3.96(4) 0 0.022(15) 0.05(2) 0.12(2) 0.171(13) -0.014(11) -0.056(13) -0.106(11) 0.011(11) 0.305(19) 0.004(15) -0.034(18) 0.243(17) 0.010(16) 0.007(13) 0.015(14) 0.01(3) -0.006(17) -0.06(3) -0.02(2) -0.01(2) 0.005(18) 0.01(2) 0.016(16) -0.040(15) 1.0238(13) 0.843(5) 0.843074 0.843074 0.843074 0.843074 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(21) 4.00(3) 0 0.007(15) -0.01(2) -0.136(18) 0.017(13) -0.030(10) -0.012(13) -0.224(12) -0.006(11) 0.437(19) 0.003(13) -0.082(18) 0.197(16) 0.011(16) -0.020(14) -0.041(15) 0.05(2) -0.013(17) -0.08(3) -0.006(19) -0.02(2) 0.013(16) -0.039(18) 0.055(16) -0.010(15) 1.0238(13) 0.843(5) 0.843074 0.843074 0.843074 0.843074 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(22) 4.39(8) 0 0.04(2) 0.05(3) 0.01(2) -0.002(17) -0.029(14) -0.020(15) 0.040(19) -0.014(16) 0.43(3) 0.08(2) -0.01(2) 0.02(2) -0.080(19) 0.04(3) -0.23(3) 0.09(3) 0.09(2) 0.06(2) -0.02(2) 0.05(2) -0.03(3) 0.10(2) -0.07(2) 0.03(2) 1.000(6) 0.77(2) 0.767604 0.767604 0.767604 0.767604 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 H(22A) 0.82(3) 0 -0.058(15) -0.075(15) 0.129(12) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(22B) 0.78(3) 0 0.021(15) 0.007(17) 0.116(14) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(22C) 0.76(3) 0 0.077(16) 0.035(15) 0.085(13) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(17) 0.839(19) 0 0.028(11) -0.037(12) 0.141(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(9) 0.859(19) 0 -0.013(11) -0.001(12) 0.130(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(4) 0.879(19) 0 -0.024(11) 0.012(11) 0.158(10) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(14) 0.853(19) 0 -0.025(11) 0.024(12) 0.127(10) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(3) 0.828(19) 0 -0.028(11) -0.012(12) 0.148(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(6) 0.870(19) 0 -0.035(11) -0.001(12) 0.129(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(7) 0.868(19) 0 0.014(12) -0.023(12) 0.125(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(12) 0.843(19) 0 -0.016(11) -0.059(12) 0.140(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(16) 0.848(19) 0 -0.025(12) 0.010(13) 0.115(10) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(15) 0.85(2) 0 -0.064(12) -0.057(13) 0.118(10) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(11) 0.89(2) 0 -0.007(12) 0.013(13) 0.128(10) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(10) 0.87(2) 0 0.015(12) 0.023(12) 0.121(10) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 loop_ _atom_local_axes_atom_label _atom_local_axes_atom0 _atom_local_axes_ax1 _atom_local_axes_atom1 _atom_local_axes_atom2 _atom_local_axes_ax2 O(1) C(1) Z O(1) C(2) Y O(13) C(19) Z O(13) C(21) Y N(8) C(18) Z N(8) C(20) Y C(1) O(1) Z C(1) C(2) Y C(2) C(3) Z C(2) C(7) Y C(3) H(3) Z C(3) C(4) Y C(4) H(4) Z C(4) C(3) Y C(5) C(4) Z C(5) C(6) Y C(6) H(6) Z C(6) C(7) Y C(7) H(7) Z C(7) C(6) Y C(9) H(9) Z C(9) C(10) Y C(10) H(10) Z C(10) C(11) Y C(11) H(11) Z C(11) C(10) Y C(12) H(12) Z C(12) C(21) Y C(14) H(14) Z C(14) C(19) Y C(15) H(15) Z C(15) C(16) Y C(16) H(16) Z C(16) C(15) Y C(17) H(17) Z C(17) C(16) Y C(18) C(17) Z C(18) C(19) Y C(19) O(13) Z C(19) C(14) Y C(20) C(9) Z C(20) C(21) Y C(21) O(13) Z C(21) C(12) Y C(22) H(22A) Z C(22) H(22B) Y H(22A) C(22) Z H(22A) H(22C) Y H(22B) C(22) Z H(22B) H(22C) Y H(22C) C(22) Z H(22C) H(22A) Y H(17) C(17) Z H(17) C(18) Y H(9) C(9) Z H(9) C(20) Y H(4) C(4) Z H(4) C(5) Y H(14) C(14) Z H(14) C(19) Y H(3) C(3) Z H(3) C(4) Y H(6) C(6) Z H(6) C(5) Y H(7) C(7) Z H(7) C(6) Y H(12) C(12) Z H(12) C(21) Y H(16) C(16) Z H(16) C(15) Y H(15) C(15) Z H(15) C(14) Y H(11) C(11) Z H(11) C(12) Y H(10) C(10) Z H(10) C(11) Y # Attachment '- pas_xd.cif' data_PAS _database_code_depnum_ccdc_archive 'CCDC 852715' #TrackingRef '- pas_xd.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_melting_point 'not measured' _chemical_formula_moiety 'C20 H15 N1 O1 S1' _chemical_formula_sum 'C20 H15 N1 O1 S1' _chemical_formula_weight 317.39 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _space_group_IT_number 14 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z _cell_length_a 8.85080(10) _cell_length_b 7.66500(10) _cell_length_c 22.6191(3) _cell_angle_alpha 90 _cell_angle_beta 91.7340(10) _cell_angle_gamma 90 _cell_volume 1533.81(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1003 _cell_measurement_theta_min 2.09 _cell_measurement_theta_max 30.0 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description cuboid _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.971 _exptl_absorpt_correction_T_max 1.007 _exptl_absorpt_process_details ; R. H. Blessing, Acta Cryst., 1995, A51, 33-38 ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'rotating-anode X-ray source' _diffrn_radiation_source 'TXS rotating anode' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'multi-layer optics' _diffrn_radiation_probe X-ray _diffrn_detector 'APEXII CCD camera' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker APEXII' _diffrn_measurement_method 'omega scans' _diffrn_orient_matrix_type 'X-axis to radiation source' _diffrn_orient_matrix_UB_11 0.758907E-1 _diffrn_orient_matrix_UB_12 -0.486835E-1 _diffrn_orient_matrix_UB_13 -0.274095E-1 _diffrn_orient_matrix_UB_21 -0.826186E-1 _diffrn_orient_matrix_UB_22 -0.621368E-1 _diffrn_orient_matrix_UB_23 -0.225889E-1 _diffrn_orient_matrix_UB_31 -0.138538E-1 _diffrn_orient_matrix_UB_32 0.103872 _diffrn_orient_matrix_UB_33 -0.263593E-1 _diffrn_reflns_number 86058 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_av_r_equivalents 0.0387 _diffrn_reflns_theta_max 45.32 _diffrn_reflns_theta_min 1.8 _diffrn_measured_fraction_theta_max 1.00 _reflns_number_total 12880 _reflns_number_gt 10010 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R. H. Blessing, Cryst. Rev., 1987, 1, 3-58 R. H. Blessing, J. Appl. Cryst., 1989, 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 software' _computing_cell_refinement 'Bruker APEX2 software' _computing_data_reduction ; SAINT intergration software, Bruker AXS SORTAV, R. H. Blessing, Acta Cryst., 1995, A51, 33-38 ; _computing_structure_solution ; SHELXS-97, G. M. Sheldrick, Acta. Cryst., 2008, A64, 112-122 ; _computing_structure_refinement ; SHELXS-97, G. M. Sheldrick, Acta. Cryst., 2008, A64, 112-122 XD2006, A. Volkov et al., 2006 ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w2 = 1/[s^2^(Fo^2^)] ; _refine_ls_extinction_method none _refine_ls_number_reflns 10003 _refine_ls_number_parameters 852 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.039 _refine_ls_R_factor_gt 0.017 _refine_ls_wR_factor_ref 0.03 _refine_ls_goodness_of_fit_ref 1.345 _refine_ls_shift/su_max 0 _refine_diff_density_max 0.264 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.029 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_symmetry_multiplicity S(13) 0.722216(7) -0.294822(8) 0.219529(3) 0.019 1 4 O(1) 0.27424(2) 0.67669(2) 0.024104(9) 0.022 1 4 N(8) 0.565306(18) -0.00713(2) 0.145003(8) 0.013 1 4 C(1) 0.26519(2) 0.52440(3) 0.008556(9) 0.014 1 4 C(2) 0.34642(2) 0.38514(3) 0.043044(8) 0.012 1 4 C(3) 0.43991(2) 0.43132(3) 0.091765(9) 0.014 1 4 C(4) 0.51275(2) 0.30322(3) 0.125281(9) 0.014 1 4 C(5) 0.49221(2) 0.12729(3) 0.110329(9) 0.012 1 4 C(6) 0.40127(2) 0.07991(3) 0.061896(9) 0.014 1 4 C(7) 0.32868(2) 0.20936(3) 0.028320(9) 0.014 1 4 C(9) 0.36325(2) 0.03025(3) 0.215366(10) 0.016 1 4 C(10) 0.30001(2) -0.00445(3) 0.269815(10) 0.018 1 4 C(11) 0.37300(3) -0.11482(3) 0.310188(10) 0.018 1 4 C(12) 0.50623(2) -0.19632(3) 0.294269(10) 0.017 1 4 C(14) 0.96037(2) -0.17509(3) 0.159587(11) 0.019 1 4 C(15) 1.03046(2) -0.08583(3) 0.114312(11) 0.02 1 4 C(16) 0.94489(2) 0.02838(3) 0.079291(10) 0.018 1 4 C(17) 0.79227(2) 0.05618(3) 0.090049(9) 0.015 1 4 C(18) 0.72040(2) -0.03354(3) 0.135285(9) 0.012 1 4 C(19) 0.80664(2) -0.15354(3) 0.169053(9) 0.015 1 4 C(20) 0.49960(2) -0.04710(2) 0.199508(9) 0.012 1 4 C(21) 0.56682(2) -0.16709(3) 0.239045(9) 0.014 1 4 C(22) 0.17127(3) 0.47278(3) -0.045260(11) 0.021 1 4 H(3) 0.453144 0.568064 0.102795 0.028 1 4 H(4) 0.583631 0.339183 0.163207 0.026 1 4 H(6) 0.38794 -0.057108 0.051275 0.028 1 4 H(7) 0.255886 0.169622 -0.008605 0.029 1 4 H(9) 0.306113 0.11898 0.184873 0.027 1 4 H(10) 0.197322 0.061461 0.282033 0.031 1 4 H(11) 0.326378 -0.135696 0.353339 0.034 1 4 H(12) 0.566251 -0.284104 0.324244 0.035 1 4 H(14) 1.023783 -0.265506 0.187514 0.037 1 4 H(15) 1.147433 -0.108802 0.103919 0.035 1 4 H(16) 0.99489 0.098418 0.043185 0.03 1 4 H(17) 0.729351 0.14735 0.062241 0.027 1 4 H(22A) 0.119218 0.586838 -0.062718 0.043 1 4 H(22B) 0.086552 0.382078 -0.034044 0.04 1 4 H(22C) 0.239519 0.410743 -0.076663 0.04 1 4 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 S(13) 0.018903 0.015493 0.023799 0.006824 0.003056 0.005291 O(1) 0.031895 0.013061 0.020502 -0.000118 -0.00463 0.003029 N(8) 0.011949 0.014708 0.013118 0.003178 0.001312 0.001797 C(1) 0.016216 0.01352 0.013634 0.001423 -0.000527 0.000637 C(2) 0.013223 0.01183 0.011521 0.000312 -0.000101 -0.000211 C(3) 0.015623 0.012057 0.013422 -0.00037 -0.001504 -0.000833 C(4) 0.016395 0.013097 0.013696 -0.000016 -0.002786 -0.00071 C(5) 0.012894 0.012318 0.012197 0.001182 -0.000266 0.000252 C(6) 0.015332 0.011796 0.013973 -0.000175 -0.001392 -0.000462 C(7) 0.015931 0.012625 0.013082 -0.000658 -0.002296 -0.000282 C(9) 0.013202 0.016986 0.016801 0.002319 0.002735 0.001561 C(10) 0.015782 0.019823 0.018214 0.001205 0.004873 -0.000846 C(11) 0.018524 0.020235 0.016164 0.002467 0.003933 -0.003618 C(12) 0.01797 0.018161 0.015847 0.005238 0.001217 -0.002156 C(14) 0.013814 0.019223 0.022985 -0.001673 0.001619 0.004075 C(15) 0.014409 0.022141 0.023279 -0.004896 0.004707 0.001284 C(16) 0.016341 0.020507 0.01653 -0.004071 0.005087 -0.001919 C(17) 0.015175 0.016566 0.012691 -0.001021 0.002708 -0.001261 C(18) 0.012298 0.012837 0.01234 -0.00051 0.001235 0.000527 C(19) 0.013294 0.014157 0.016429 0.000196 0.001038 0.002531 C(20) 0.011846 0.012166 0.013064 0.001896 0.000992 -0.000127 C(21) 0.013873 0.013272 0.015011 0.003497 0.00069 -0.000183 C(22) 0.023679 0.019624 0.01961 0.002435 -0.007923 -0.000601 H(3) 0.038398 0.01614 0.029468 -0.003101 -0.004633 -0.000081 H(4) 0.030003 0.025829 0.021523 -0.002703 -0.007248 -0.001289 H(6) 0.033885 0.016785 0.031729 -0.003539 -0.002212 -0.003001 H(7) 0.031903 0.028757 0.025964 -0.00296 -0.010121 -0.004119 H(9) 0.026905 0.029436 0.026052 0.007215 0.001131 0.006628 H(10) 0.024363 0.037023 0.03071 0.002022 0.007958 0.006192 H(11) 0.034946 0.042677 0.024156 0.009289 0.009391 -0.000236 H(12) 0.036081 0.036729 0.031917 0.015629 0.001293 0.007464 H(14) 0.029252 0.038833 0.041841 0.011546 0.000904 0.01263 H(15) 0.020113 0.045329 0.040806 0.000941 0.007575 0.007247 H(16) 0.027261 0.036083 0.027038 0.002857 0.008345 -0.002931 H(17) 0.025814 0.027656 0.026397 0.005729 0.000421 0.002873 H(22A) 0.053741 0.032066 0.042978 0.006954 -0.018743 0.007823 H(22B) 0.039098 0.045221 0.036734 0.006617 -0.00562 -0.014352 H(22C) 0.037683 0.049304 0.03151 -0.00855 -0.002809 0.003252 #----------------------------------------------------------------------------# # MULTIPOLE PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_rho_multipole_atom_label _atom_rho_multipole_coeff_Pv _atom_rho_multipole_coeff_P00 _atom_rho_multipole_coeff_P11 _atom_rho_multipole_coeff_P1-1 _atom_rho_multipole_coeff_P10 _atom_rho_multipole_coeff_P20 _atom_rho_multipole_coeff_P21 _atom_rho_multipole_coeff_P2-1 _atom_rho_multipole_coeff_P22 _atom_rho_multipole_coeff_P2-2 _atom_rho_multipole_coeff_P30 _atom_rho_multipole_coeff_P31 _atom_rho_multipole_coeff_P3-1 _atom_rho_multipole_coeff_P32 _atom_rho_multipole_coeff_P3-2 _atom_rho_multipole_coeff_P33 _atom_rho_multipole_coeff_P3-3 _atom_rho_multipole_coeff_P40 _atom_rho_multipole_coeff_P41 _atom_rho_multipole_coeff_P4-1 _atom_rho_multipole_coeff_P42 _atom_rho_multipole_coeff_P4-2 _atom_rho_multipole_coeff_P43 _atom_rho_multipole_coeff_P4-3 _atom_rho_multipole_coeff_P44 _atom_rho_multipole_coeff_P4-4 _atom_rho_multipole_kappa _atom_rho_multipole_kappa_prime0 _atom_rho_multipole_kappa_prime1 _atom_rho_multipole_kappa_prime2 _atom_rho_multipole_kappa_prime3 _atom_rho_multipole_kappa_prime4 _atom_rho_multipole_radial_slater_n0 _atom_rho_multipole_radial_slater_zeta0 _atom_rho_multipole_radial_slater_n1 _atom_rho_multipole_radial_slater_zeta1 _atom_rho_multipole_radial_slater_n2 _atom_rho_multipole_radial_slater_zeta2 _atom_rho_multipole_radial_slater_n3 _atom_rho_multipole_radial_slater_zeta3 _atom_rho_multipole_radial_slater_n4 _atom_rho_multipole_radial_slater_zeta4 S(13) 5.7003 0 -0.0204 -0.0036 -0.054 -0.084 -0.0209 0.1002 0.1223 -0.0106 0.0704 0.0181 -0.069 0.0724 0.0623 0.0428 0.0489 0.0534 0.0525 0.0105 0.0143 -0.0023 -0.0218 0.0518 0.0311 -0.019 1.063902 1.182327 1.182327 1.182327 1.182327 1.182327 4 3.8512666666667 4 3.8512666666667 4 3.8512666666667 4 3.8512666666667 4 3.8512666666667 O(1) 6.0877 0 -0.0005 0.0112 -0.0379 0.0411 -0.0121 -0.0095 -0.1237 0.005 0.0261 -0.0238 -0.021 0.0572 0.0176 0.0077 0.0224 0.0049 -0.0092 0.0106 0.0338 0.0106 0.0065 0.018 0.0312 -0.0167 1.000357 0.847979 0.847979 0.847979 0.847979 0.847979 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466 N(8) 5.0938 0 -0.0427 -0.027 -0.0315 -0.0301 -0.0059 0.0276 0.0304 0.007 0.2199 -0.0136 -0.0041 0.1459 0.053 -0.0427 -0.0266 0.0076 0.0117 -0.0045 -0.0529 0.0126 0.0119 -0.0156 0.012 -0.0216 0.993506 0.815019 0.815019 0.815019 0.815019 0.815019 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936 C(1) 4.0007 0 -0.003 0.0014 0.1099 0.2598 -0.0002 0.0004 -0.2268 -0.0026 0.3277 0.006 0.0138 0.2259 0.029 0.0129 -0.0137 0.0244 -0.0033 -0.0009 -0.0411 -0.0066 -0.041 -0.0291 0.0648 0.0275 1.004154 0.860597 0.860597 0.860597 0.860597 0.860597 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(2) 4.1154 0 -0.0228 0.0382 0.0081 0.1248 0.0004 -0.0168 -0.1949 0.0389 0.3057 -0.0048 -0.0135 0.2248 -0.0438 -0.0116 0.0194 0.0131 -0.0035 0.0488 -0.0074 0.0043 -0.0176 0.0363 0.0982 -0.0284 1.004154 0.860597 0.860597 0.860597 0.860597 0.860597 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(3) 4.0629 0 0.0164 0.0176 0.0466 0.1159 -0.0066 -0.0101 -0.2082 -0.0314 0.3262 0.0067 0.0168 0.1903 0.0225 0.0009 -0.0187 0.05 0.0026 0.0179 0.011 -0.0252 0.0006 0.0006 0.0539 0.0256 1.004154 0.860597 0.860597 0.860597 0.860597 0.860597 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(4) 4.0566 0 -0.043 0.0254 0.0224 0.1157 0.0128 -0.0354 -0.1993 0.0067 0.3117 0.0235 0.0402 0.1989 0.015 0.0266 -0.011 0.0885 0.0026 -0.0297 -0.0038 0.0016 0.0017 0.0167 0.0136 -0.0001 1.004154 0.860597 0.860597 0.860597 0.860597 0.860597 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(5) 4.0772 0 -0.051 0.1337 0.0556 0.124 0.0163 -0.0465 -0.1556 0.0366 0.2997 0.0262 -0.0102 0.268 0.0354 0.0413 -0.0244 0.0249 0.0201 0.0259 -0.0607 -0.0388 -0.0061 0.0012 0.0175 -0.0412 1.004154 0.860597 0.860597 0.860597 0.860597 0.860597 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(6) 4.1672 0 0.0181 -0.0229 -0.0136 0.1087 -0.0079 0.0269 -0.2286 0.0186 0.3293 0.0033 -0.0523 0.2095 -0.0034 -0.0027 0.0038 0.0274 0.0093 0.0169 -0.0012 -0.0322 -0.0105 0.0162 0.0762 -0.0121 1.004154 0.860597 0.860597 0.860597 0.860597 0.860597 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(7) 4.111 0 0.0319 -0.0409 0.0222 0.1072 -0.0132 -0.0085 -0.2179 0.0007 0.2913 0.0093 -0.0123 0.2017 0.0155 -0.0055 0.0061 0.0998 0.0052 -0.031 -0.0199 -0.0269 0.0086 0.0138 -0.0021 -0.0079 1.004154 0.860597 0.860597 0.860597 0.860597 0.860597 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(9) 4.162 0 -0.0205 -0.0457 0.034 0.1355 0.0178 -0.0064 -0.1418 -0.0069 0.3283 -0.0211 0.0324 0.1914 -0.0256 -0.0222 0.0267 0.0532 0.0184 -0.0536 0.0515 0.0081 -0.0056 -0.0216 0.0605 -0.0038 1.004154 0.860597 0.860597 0.860597 0.860597 0.860597 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(10) 4.1599 0 -0.0117 -0.014 -0.067 0.0734 0.0061 -0.0211 -0.201 -0.0032 0.318 0.0079 0.0312 0.2284 -0.0058 0.0003 0.0013 0.0463 -0.0355 -0.0309 -0.0333 0.0021 -0.0541 -0.0306 0.018 -0.0357 1.004154 0.860597 0.860597 0.860597 0.860597 0.860597 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(11) 4.0949 0 0.0171 -0.0182 -0.0207 0.0624 0.0143 0.0035 -0.1856 -0.0317 0.3319 -0.0184 -0.0525 0.2047 0.0301 -0.0245 0.0286 0.0427 -0.0314 0.0033 -0.0022 0.0056 -0.0118 -0.0207 0.013 -0.0202 1.004154 0.860597 0.860597 0.860597 0.860597 0.860597 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(12) 4.055 0 0.0076 -0.0522 0.0067 0.1217 0.0102 -0.0271 -0.1488 -0.0277 0.2912 -0.0284 0.0346 0.1757 0.0087 -0.0049 0.0106 0.1031 -0.0222 0.0145 0.0335 0.0088 0.0106 -0.0094 0.0275 0.0334 1.004154 0.860597 0.860597 0.860597 0.860597 0.860597 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(14) 4.052 0 0.0134 -0.0248 0.0342 0.1173 -0.0077 -0.0269 -0.1917 0.0194 0.29 0.0789 0.1195 0.1351 -0.035 0.0256 0.0141 0.1107 0.0152 0.0332 0.0719 0.0126 0.0145 -0.0071 0.0315 -0.0413 1.004154 0.860597 0.860597 0.860597 0.860597 0.860597 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(15) 4.1731 0 -0.0153 0.0171 -0.0108 0.0737 -0.0157 -0.0216 -0.2011 -0.0089 0.3394 -0.008 -0.0235 0.2132 -0.0151 -0.0262 0.014 0.0093 0.0337 0.0168 -0.0598 0.0493 0.0355 -0.018 0.0152 0.0198 1.004154 0.860597 0.860597 0.860597 0.860597 0.860597 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(16) 4.2428 0 -0.0135 0.0725 0.0331 0.0644 0.0111 -0.0379 -0.2291 0.0067 0.2879 0.0196 -0.0251 0.1691 -0.0369 0.0474 -0.0041 0.0414 0.0322 -0.0074 -0.0316 0.0137 -0.0186 -0.0175 0.0085 0.0201 1.004154 0.860597 0.860597 0.860597 0.860597 0.860597 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(17) 4.2319 0 0.0276 0.0237 0.0461 0.1276 -0.0071 -0.0063 -0.1415 0.0184 0.3541 0.0028 0.0296 0.1974 -0.0245 0.0038 0.0005 0.0593 -0.0166 -0.0086 0.0133 0.0278 -0.0121 -0.0177 0.0413 0.0025 1.004154 0.860597 0.860597 0.860597 0.860597 0.860597 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(18) 3.9322 0 0.0115 0.0475 0.0698 0.1179 -0.0037 -0.0553 -0.137 0.0008 0.2724 -0.0088 -0.0104 0.2381 -0.0081 -0.0025 0.0393 -0.0257 -0.0054 -0.0289 -0.0594 0.0001 0.0286 -0.0361 0.0126 0.0029 1.004154 0.860597 0.860597 0.860597 0.860597 0.860597 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(19) 4.2324 0 0.0304 0.0858 0.06 0.123 -0.018 -0.0271 -0.1751 -0.002 0.3272 -0.0076 0 0.2681 0.0076 -0.0552 0.03 0.0242 0.0168 0.0546 -0.0223 0.0255 0.0521 -0.0069 0.0276 0.0005 1.004154 0.860597 0.860597 0.860597 0.860597 0.860597 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(20) 3.9525 0 0.0048 0.0972 0.0599 0.1025 -0.0141 -0.0516 -0.1367 -0.0109 0.2593 0.0257 0.0201 0.2346 0.0098 -0.0194 0.065 -0.016 -0.0263 0.0041 -0.0136 0.051 -0.0261 -0.0603 0.0149 0.0108 1.004154 0.860597 0.860597 0.860597 0.860597 0.860597 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(21) 4.2236 0 -0.0669 0.0565 0.0467 0.084 -0.0082 -0.059 -0.1196 -0.0074 0.3048 -0.0401 0.0124 0.2744 0.0028 0.0263 0.0521 -0.0032 -0.077 0.0039 -0.0185 0.0378 -0.004 0.0025 0.039 -0.0225 1.004154 0.860597 0.860597 0.860597 0.860597 0.860597 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 C(22) 4.3909 0 -0.0497 0.0144 0.0416 0.0091 0.0235 0.0188 0.0212 -0.0002 0.3713 -0.0243 0.0553 -0.029 -0.0043 -0.081 -0.2625 0.0743 -0.0417 -0.0119 -0.0207 -0.0032 0.0291 0.1783 0.0373 -0.0226 0.99309 0.838202 0.838202 0.838202 0.838202 0.838202 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762 H(3) 0.8332 0 0.0079 0.0029 0.1221 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(4) 0.8241 0 -0.0013 0.0452 0.1213 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(6) 0.8629 0 -0.0085 -0.0142 0.143 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(7) 0.8589 0 -0.0315 -0.0138 0.1314 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(9) 0.8328 0 0.0132 0.0165 0.119 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(10) 0.8351 0 -0.0598 -0.0184 0.1369 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(11) 0.8769 0 0.0008 0.0053 0.1177 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(12) 0.8551 0 -0.0085 -0.0114 0.1328 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(14) 0.8029 0 0.0196 -0.0443 0.1366 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(15) 0.859 0 0.0597 -0.0446 0.1281 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(16) 0.8904 0 0.0177 -0.0272 0.1168 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(17) 0.8041 0 0.0032 -0.0203 0.1139 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(22A) 0.822 0 0.0196 0.0337 0.0791 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(22B) 0.8226 0 -0.0212 0.0036 0.0862 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 H(22C) 0.8427 0 -0.033 -0.0246 0.098 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2 loop_ _atom_local_axes_atom_label _atom_local_axes_atom0 _atom_local_axes_ax1 _atom_local_axes_atom1 _atom_local_axes_atom2 _atom_local_axes_ax2 S(13) C(21) Z S(13) C(19) Y O(1) C(1) Z O(1) C(2) Y N(8) C(18) Z N(8) C(20) Y C(1) O(1) Z C(1) C(2) Y C(2) C(7) Z C(2) C(3) Y C(3) H(3) Z C(3) C(4) Y C(4) H(4) Z C(4) C(3) Y C(5) C(6) Z C(5) C(4) Y C(6) H(6) Z C(6) C(5) Y C(7) H(7) Z C(7) C(6) Y C(9) H(9) Z C(9) C(10) Y C(10) H(10) Z C(10) C(11) Y C(11) H(11) Z C(11) C(10) Y C(12) H(12) Z C(12) C(11) Y C(14) H(14) Z C(14) C(15) Y C(15) H(15) Z C(15) C(16) Y C(16) H(16) Z C(16) C(15) Y C(17) H(17) Z C(17) C(16) Y C(18) C(17) Z C(18) C(19) Y C(19) C(14) Z C(19) C(18) Y C(20) C(9) Z C(20) C(21) Y C(21) C(12) Z C(21) C(20) Y C(22) H(22A) Z C(22) H(22C) Y H(3) C(3) Z H(3) C(2) Y H(4) C(4) Z H(4) C(5) Y H(6) C(6) Z H(6) C(5) Y H(7) C(7) Z H(7) C(6) Y H(9) C(9) Z H(9) C(10) Y H(10) C(10) Z H(10) C(11) Y H(11) C(11) Z H(11) C(12) Y H(12) C(12) Z H(12) C(21) Y H(14) C(14) Z H(14) C(15) Y H(15) C(15) Z H(15) C(16) Y H(16) C(16) Z H(16) C(17) Y H(17) C(17) Z H(17) C(16) Y H(22A) C(22) Z H(22A) H(22C) Y H(22B) C(22) Z H(22B) H(22A) Y H(22C) C(22) Z H(22C) H(22A) Y #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S(13) C(19) 1.7568(2) 1_555 1_555 yes S(13) C(21) 1.7555(2) 1_555 1_555 yes O(1) C(1) 1.2211(3) 1_555 1_555 yes N(8) C(5) 1.4369(2) 1_555 1_555 yes N(8) C(18) 1.4113(2) 1_555 1_555 yes N(8) C(20) 1.4126(3) 1_555 1_555 yes C(1) C(2) 1.4936(3) 1_555 1_555 yes C(1) C(22) 1.5060(3) 1_555 1_555 yes C(2) C(3) 1.4033(3) 1_555 1_555 yes C(2) C(7) 1.3956(3) 1_555 1_555 yes C(3) C(4) 1.3874(3) 1_555 1_555 yes C(3) H(3) 1.0830(2) 1_555 1_555 yes C(4) C(5) 1.4008(3) 1_555 1_555 yes C(4) H(4) 1.08299(19) 1_555 1_555 yes C(5) C(6) 1.3880(3) 1_555 1_555 yes C(6) C(7) 1.3945(3) 1_555 1_555 yes C(6) H(6) 1.0830(2) 1_555 1_555 yes C(7) H(7) 1.08300(18) 1_555 1_555 yes C(9) C(10) 1.3937(3) 1_555 1_555 yes C(9) C(20) 1.4010(3) 1_555 1_555 yes C(9) H(9) 1.0830(2) 1_555 1_555 yes C(10) C(11) 1.3897(3) 1_555 1_555 yes C(10) H(10) 1.0830(2) 1_555 1_555 yes C(11) C(12) 1.3914(3) 1_555 1_555 yes C(11) H(11) 1.0830(2) 1_555 1_555 yes C(12) C(21) 1.3923(3) 1_555 1_555 yes C(12) H(12) 1.0830(2) 1_555 1_555 yes C(14) C(15) 1.3929(4) 1_555 1_555 yes C(14) C(19) 1.3936(3) 1_555 1_555 yes C(14) H(14) 1.0830(2) 1_555 1_555 yes C(15) C(16) 1.3896(3) 1_555 1_555 yes C(15) H(15) 1.0830(2) 1_555 1_555 yes C(16) C(17) 1.3961(3) 1_555 1_555 yes C(16) H(16) 1.0830(2) 1_555 1_555 yes C(17) C(18) 1.4014(3) 1_555 1_555 yes C(17) H(17) 1.0830(2) 1_555 1_555 yes C(18) C(19) 1.4060(3) 1_555 1_555 yes C(20) C(21) 1.4026(3) 1_555 1_555 yes C(22) H(22A) 1.0590(2) 1_555 1_555 yes C(22) H(22B) 1.0590(3) 1_555 1_555 yes C(22) H(22C) 1.0590(3) 1_555 1_555 yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(19) S(13) C(21) 99.874(9) 1_555 1_555 1_555 yes C(5) N(8) C(18) 116.220(16) 1_555 1_555 1_555 yes C(5) N(8) C(20) 116.197(16) 1_555 1_555 1_555 yes C(18) N(8) C(20) 122.200(15) 1_555 1_555 1_555 yes O(1) C(1) C(2) 120.425(18) 1_555 1_555 1_555 yes O(1) C(1) C(22) 120.913(19) 1_555 1_555 1_555 yes C(2) C(1) C(22) 118.661(18) 1_555 1_555 1_555 yes C(1) C(2) C(3) 119.538(18) 1_555 1_555 1_555 yes C(1) C(2) C(7) 121.089(17) 1_555 1_555 1_555 yes C(3) C(2) C(7) 119.361(17) 1_555 1_555 1_555 yes C(2) C(3) C(4) 120.255(18) 1_555 1_555 1_555 yes C(2) C(3) H(3) 118.824(18) 1_555 1_555 1_555 yes C(4) C(3) H(3) 120.919(17) 1_555 1_555 1_555 yes C(3) C(4) C(5) 119.642(17) 1_555 1_555 1_555 yes C(3) C(4) H(4) 120.076(19) 1_555 1_555 1_555 yes C(5) C(4) H(4) 120.275(18) 1_555 1_555 1_555 yes N(8) C(5) C(4) 120.366(17) 1_555 1_555 1_555 yes N(8) C(5) C(6) 118.944(18) 1_555 1_555 1_555 yes C(4) C(5) C(6) 120.690(17) 1_555 1_555 1_555 yes C(5) C(6) C(7) 119.359(18) 1_555 1_555 1_555 yes C(5) C(6) H(6) 119.045(18) 1_555 1_555 1_555 yes C(7) C(6) H(6) 121.594(17) 1_555 1_555 1_555 yes C(2) C(7) C(6) 120.685(17) 1_555 1_555 1_555 yes C(2) C(7) H(7) 121.035(18) 1_555 1_555 1_555 yes C(6) C(7) H(7) 118.257(18) 1_555 1_555 1_555 yes C(10) C(9) C(20) 121.167(19) 1_555 1_555 1_555 yes C(10) C(9) H(9) 119.363(19) 1_555 1_555 1_555 yes C(20) C(9) H(9) 119.469(19) 1_555 1_555 1_555 yes C(9) C(10) C(11) 120.38(2) 1_555 1_555 1_555 yes C(9) C(10) H(10) 119.94(2) 1_555 1_555 1_555 yes C(11) C(10) H(10) 119.56(2) 1_555 1_555 1_555 yes C(10) C(11) C(12) 118.95(2) 1_555 1_555 1_555 yes C(10) C(11) H(11) 119.99(2) 1_555 1_555 1_555 yes C(12) C(11) H(11) 121.06(2) 1_555 1_555 1_555 yes C(11) C(12) C(21) 120.820(19) 1_555 1_555 1_555 yes C(11) C(12) H(12) 121.36(2) 1_555 1_555 1_555 yes C(21) C(12) H(12) 117.82(2) 1_555 1_555 1_555 yes C(15) C(14) C(19) 120.89(2) 1_555 1_555 1_555 yes C(15) C(14) H(14) 120.58(2) 1_555 1_555 1_555 yes C(19) C(14) H(14) 118.51(2) 1_555 1_555 1_555 yes C(14) C(15) C(16) 118.78(2) 1_555 1_555 1_555 yes C(14) C(15) H(15) 121.98(2) 1_555 1_555 1_555 yes C(16) C(15) H(15) 119.13(2) 1_555 1_555 1_555 yes C(15) C(16) C(17) 120.68(2) 1_555 1_555 1_555 yes C(15) C(16) H(16) 120.94(2) 1_555 1_555 1_555 yes C(17) C(16) H(16) 118.38(2) 1_555 1_555 1_555 yes C(16) C(17) C(18) 121.019(19) 1_555 1_555 1_555 yes C(16) C(17) H(17) 118.72(2) 1_555 1_555 1_555 yes C(18) C(17) H(17) 120.255(18) 1_555 1_555 1_555 yes N(8) C(18) C(17) 120.564(17) 1_555 1_555 1_555 yes N(8) C(18) C(19) 121.589(18) 1_555 1_555 1_555 yes C(17) C(18) C(19) 117.819(18) 1_555 1_555 1_555 yes S(13) C(19) C(14) 117.596(16) 1_555 1_555 1_555 yes S(13) C(19) C(18) 121.449(15) 1_555 1_555 1_555 yes C(14) C(19) C(18) 120.71(2) 1_555 1_555 1_555 yes N(8) C(20) C(9) 120.812(17) 1_555 1_555 1_555 yes N(8) C(20) C(21) 121.386(17) 1_555 1_555 1_555 yes C(9) C(20) C(21) 117.794(18) 1_555 1_555 1_555 yes S(13) C(21) C(12) 117.502(15) 1_555 1_555 1_555 yes S(13) C(21) C(20) 121.721(16) 1_555 1_555 1_555 yes C(12) C(21) C(20) 120.669(19) 1_555 1_555 1_555 yes C(1) C(22) H(22A) 107.93(2) 1_555 1_555 1_555 yes C(1) C(22) H(22B) 110.88(2) 1_555 1_555 1_555 yes C(1) C(22) H(22C) 110.366(19) 1_555 1_555 1_555 yes H(22A) C(22) H(22B) 109.15(2) 1_555 1_555 1_555 yes H(22A) C(22) H(22C) 111.78(2) 1_555 1_555 1_555 yes H(22B) C(22) H(22C) 106.75(2) 1_555 1_555 1_555 yes 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 C(19) S(13) C(21) C(12) -154.086(19) 1_555 1_555 1_555 1_555 yes C(21) S(13) C(19) C(14) 156.600(19) 1_555 1_555 1_555 1_555 yes C(21) S(13) C(19) C(18) -29.108(17) 1_555 1_555 1_555 1_555 yes C(19) S(13) C(21) C(20) 29.664(17) 1_555 1_555 1_555 1_555 yes C(18) N(8) C(5) C(4) -77.51(2) 1_555 1_555 1_555 1_555 yes C(18) N(8) C(5) C(6) 102.45(2) 1_555 1_555 1_555 1_555 yes C(5) N(8) C(18) C(17) -6.008(18) 1_555 1_555 1_555 1_555 yes C(5) N(8) C(18) C(19) 175.97(3) 1_555 1_555 1_555 1_555 yes C(20) N(8) C(5) C(4) 77.22(2) 1_555 1_555 1_555 1_555 yes C(20) N(8) C(5) C(6) -102.82(2) 1_555 1_555 1_555 1_555 yes C(5) N(8) C(20) C(9) 5.593(18) 1_555 1_555 1_555 1_555 yes C(5) N(8) C(20) C(21) -175.45(3) 1_555 1_555 1_555 1_555 yes C(18) N(8) C(20) C(9) 158.68(3) 1_555 1_555 1_555 1_555 yes C(20) N(8) C(18) C(17) -159.09(3) 1_555 1_555 1_555 1_555 yes C(20) N(8) C(18) C(19) 22.883(19) 1_555 1_555 1_555 1_555 yes C(18) N(8) C(20) C(21) -22.365(18) 1_555 1_555 1_555 1_555 yes O(1) C(1) C(2) C(3) -3.35(2) 1_555 1_555 1_555 1_555 yes O(1) C(1) C(2) C(7) 175.41(3) 1_555 1_555 1_555 1_555 yes O(1) C(1) C(22) H(22A) -1.79(2) 1_555 1_555 1_555 1_555 yes O(1) C(1) C(22) H(22B) -121.29(3) 1_555 1_555 1_555 1_555 yes O(1) C(1) C(22) H(22C) 120.64(3) 1_555 1_555 1_555 1_555 yes C(22) C(1) C(2) C(3) 177.16(3) 1_555 1_555 1_555 1_555 yes C(22) C(1) C(2) C(7) -4.078(19) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(22) H(22A) 177.70(3) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(22) H(22B) 58.20(2) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(22) H(22C) -59.88(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(4) 178.16(3) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) H(3) -1.334(17) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(7) C(6) -177.98(3) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(7) H(7) 0.251(17) 1_555 1_555 1_555 1_555 yes C(7) C(2) C(3) C(4) -0.624(19) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(7) C(6) 0.781(19) 1_555 1_555 1_555 1_555 yes C(7) C(2) C(3) H(3) 179.88(3) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(7) H(7) 179.01(3) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) C(5) -0.165(18) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) H(4) -179.18(3) 1_555 1_555 1_555 1_555 yes H(3) C(3) C(4) C(5) 179.32(3) 1_555 1_555 1_555 1_555 yes H(3) C(3) C(4) H(4) 0.304(17) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(5) N(8) -179.22(3) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(5) C(6) 0.819(19) 1_555 1_555 1_555 1_555 yes H(4) C(4) C(5) N(8) -0.214(17) 1_555 1_555 1_555 1_555 yes H(4) C(4) C(5) C(6) 179.83(3) 1_555 1_555 1_555 1_555 yes N(8) C(5) C(6) C(7) 179.38(3) 1_555 1_555 1_555 1_555 yes N(8) C(5) C(6) H(6) -0.261(17) 1_555 1_555 1_555 1_555 yes C(4) C(5) C(6) C(7) -0.665(19) 1_555 1_555 1_555 1_555 yes C(4) C(5) C(6) H(6) 179.70(3) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(7) C(2) -0.140(18) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(7) H(7) -178.42(3) 1_555 1_555 1_555 1_555 yes H(6) C(6) C(7) C(2) 179.49(3) 1_555 1_555 1_555 1_555 yes H(6) C(6) C(7) H(7) 1.207(17) 1_555 1_555 1_555 1_555 yes C(10) C(9) C(20) N(8) -178.05(3) 1_555 1_555 1_555 1_555 yes C(20) C(9) C(10) C(11) 1.20(2) 1_555 1_555 1_555 1_555 yes C(10) C(9) C(20) C(21) 2.97(2) 1_555 1_555 1_555 1_555 yes C(20) C(9) C(10) H(10) 177.10(3) 1_555 1_555 1_555 1_555 yes H(9) C(9) C(10) C(11) -178.56(3) 1_555 1_555 1_555 1_555 yes H(9) C(9) C(10) H(10) -2.666(19) 1_555 1_555 1_555 1_555 yes H(9) C(9) C(20) N(8) 1.717(18) 1_555 1_555 1_555 1_555 yes H(9) C(9) C(20) C(21) -177.27(3) 1_555 1_555 1_555 1_555 yes C(9) C(10) C(11) C(12) -3.00(2) 1_555 1_555 1_555 1_555 yes C(9) C(10) C(11) H(11) 176.67(3) 1_555 1_555 1_555 1_555 yes H(10) C(10) C(11) C(12) -178.91(3) 1_555 1_555 1_555 1_555 yes H(10) C(10) C(11) H(11) 0.76(2) 1_555 1_555 1_555 1_555 yes C(10) C(11) C(12) C(21) 0.58(2) 1_555 1_555 1_555 1_555 yes C(10) C(11) C(12) H(12) -179.51(3) 1_555 1_555 1_555 1_555 yes H(11) C(11) C(12) C(21) -179.08(3) 1_555 1_555 1_555 1_555 yes H(11) C(11) C(12) H(12) 0.83(2) 1_555 1_555 1_555 1_555 yes C(11) C(12) C(21) S(13) -172.61(3) 1_555 1_555 1_555 1_555 yes C(11) C(12) C(21) C(20) 3.68(2) 1_555 1_555 1_555 1_555 yes H(12) C(12) C(21) S(13) 7.477(15) 1_555 1_555 1_555 1_555 yes H(12) C(12) C(21) C(20) -176.23(3) 1_555 1_555 1_555 1_555 yes C(15) C(14) C(19) S(13) 170.66(3) 1_555 1_555 1_555 1_555 yes C(19) C(14) C(15) C(16) 1.29(2) 1_555 1_555 1_555 1_555 yes C(15) C(14) C(19) C(18) -3.68(2) 1_555 1_555 1_555 1_555 yes C(19) C(14) C(15) H(15) -174.82(4) 1_555 1_555 1_555 1_555 yes H(14) C(14) C(15) C(16) 179.68(4) 1_555 1_555 1_555 1_555 yes H(14) C(14) C(15) H(15) 3.56(2) 1_555 1_555 1_555 1_555 yes H(14) C(14) C(19) S(13) -7.761(16) 1_555 1_555 1_555 1_555 yes H(14) C(14) C(19) C(18) 177.90(3) 1_555 1_555 1_555 1_555 yes C(14) C(15) C(16) C(17) 1.39(2) 1_555 1_555 1_555 1_555 yes C(14) C(15) C(16) H(16) -178.92(4) 1_555 1_555 1_555 1_555 yes H(15) C(15) C(16) C(17) 177.62(4) 1_555 1_555 1_555 1_555 yes H(15) C(15) C(16) H(16) -2.69(2) 1_555 1_555 1_555 1_555 yes C(15) C(16) C(17) C(18) -1.74(2) 1_555 1_555 1_555 1_555 yes C(15) C(16) C(17) H(17) 179.22(3) 1_555 1_555 1_555 1_555 yes H(16) C(16) C(17) C(18) 178.57(3) 1_555 1_555 1_555 1_555 yes H(16) C(16) C(17) H(17) -0.476(18) 1_555 1_555 1_555 1_555 yes C(16) C(17) C(18) N(8) -178.69(3) 1_555 1_555 1_555 1_555 yes C(16) C(17) C(18) C(19) -0.593(19) 1_555 1_555 1_555 1_555 yes H(17) C(17) C(18) N(8) 0.339(17) 1_555 1_555 1_555 1_555 yes H(17) C(17) C(18) C(19) 178.44(3) 1_555 1_555 1_555 1_555 yes N(8) C(18) C(19) S(13) 7.222(15) 1_555 1_555 1_555 1_555 yes N(8) C(18) C(19) C(14) -178.66(3) 1_555 1_555 1_555 1_555 yes C(17) C(18) C(19) S(13) -170.85(3) 1_555 1_555 1_555 1_555 yes C(17) C(18) C(19) C(14) 3.26(2) 1_555 1_555 1_555 1_555 yes N(8) C(20) C(21) S(13) -8.220(15) 1_555 1_555 1_555 1_555 yes N(8) C(20) C(21) C(12) 175.65(3) 1_555 1_555 1_555 1_555 yes C(9) C(20) C(21) S(13) 170.76(3) 1_555 1_555 1_555 1_555 yes C(9) C(20) C(21) C(12) -5.370(19) 1_555 1_555 1_555 1_555 yes # Attachment '- pbo_xd.cif' data_PBO _database_code_depnum_ccdc_archive 'CCDC 852716' #TrackingRef '- pbo_xd.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_melting_point 'not measured' _chemical_formula_moiety 'C25 H17 N1 O2' _chemical_formula_sum 'C25 H17 N1 O2' _chemical_formula_weight 363.4 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z _cell_length_a 8.3769(3) _cell_length_b 29.7404(11) _cell_length_c 7.7536(3) _cell_angle_alpha 90 _cell_angle_beta 117.130(2) _cell_angle_gamma 90 _cell_volume 1719.14(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3000 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 30.0 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description cuboid _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details ; R. H. Blessing, Acta Cryst., 1995, A51, 33-38 ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'rotating-anode X-ray source' _diffrn_radiation_source 'TXS rotating anode' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'multi-layer optics' _diffrn_radiation_probe X-ray _diffrn_detector 'APEXII CCD camera' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker APEXII' _diffrn_measurement_method 'omega scans' _diffrn_orient_matrix_type 'X-axis to radiation source' _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_number 82376 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 59 _diffrn_reflns_limit_k_min -54 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_theta_max 45.3 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_av_r_equivalents 0.064 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 14405 _reflns_number_gt 7843 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R. H. Blessing, Cryst. Rev., 1987, 1, 3-58 R. H. Blessing, J. Appl. Cryst., 1989, 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 software' _computing_cell_refinement 'Bruker APEX2 software' _computing_data_reduction ; SAINT intergration software, Bruker AXS SORTAV, R. H. Blessing, Acta Cryst., 1995, A51, 33-38 ; _computing_structure_solution ; SHELXS-97, G. M. Sheldrick, Acta. Cryst., 2008, A64, 112-122 ; _computing_structure_refinement ; SHELXS-97, G. M. Sheldrick, Acta. Cryst., 2008, A64, 112-122 XD2006, A. Volkov et al., 2006 ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# # Refinement details _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.026 _refine_ls_R_factor_all 0.054 _refine_ls_R_Fsqd_factor 0.037 _refine_ls_wR_factor_ref 0.055 _refine_ls_hydrogen_treatment ? _refine_ls_number_reflns 7743 _refine_ls_number_parameters 85 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w2 = 1/[s^2^(Fo^2^)] ; _refine_ls_shift/su_max 0 _refine_ls_extinction_method none _refine_diff_density_max 0.219 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.043 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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_occupancy _atom_site_symmetry_multiplicity O(1) O -0.00459(5) 0.246361(14) -0.26079(7) 0.026 1 4 O(13) O 0.72042(5) 0.007405(12) 0.28942(5) 0.017 1 4 N(8) N 0.45520(5) 0.074271(13) 0.13274(5) 0.014 1 4 C(1) C -0.06816(6) 0.210485(15) -0.24431(6) 0.015 1 4 C(2) C 0.05588(5) 0.172501(14) -0.14093(6) 0.013 1 4 C(3) C 0.04778(6) 0.131654(15) -0.23345(6) 0.014 1 4 C(4) C 0.18096(5) 0.099451(15) -0.14354(6) 0.013 1 4 C(5) C 0.31776(5) 0.107036(14) 0.04308(6) 0.012 1 4 C(6) C 0.31892(6) 0.146584(15) 0.14046(6) 0.014 1 4 C(7) C 0.19074(6) 0.179597(15) 0.04707(6) 0.014 1 4 C(9) C 0.24445(6) 0.021710(15) 0.16532(6) 0.014 1 4 C(10) C 0.21116(6) -0.020141(16) 0.22389(6) 0.016 1 4 C(11) C 0.34693(7) -0.051761(16) 0.30445(7) 0.017 1 4 C(12) C 0.51697(6) -0.041556(15) 0.32498(6) 0.016 1 4 C(14) C 0.94599(6) 0.059859(17) 0.33625(6) 0.016 1 4 C(15) C 1.00245(6) 0.102763(17) 0.31606(6) 0.017 1 4 C(16) C 0.87692(6) 0.136897(17) 0.23796(6) 0.016 1 4 C(17) C 0.69566(6) 0.128257(16) 0.17944(6) 0.015 1 4 C(18) C 0.63635(5) 0.085310(15) 0.19586(5) 0.012 1 4 C(19) C 0.76595(5) 0.051326(15) 0.27497(6) 0.013 1 4 C(20) C 0.41396(5) 0.032159(14) 0.18429(5) 0.012 1 4 C(21) C 0.54880(6) -0.000308(14) 0.26476(6) 0.013 1 4 C(22) C -0.26482(5) 0.204961(14) -0.32012(6) 0.012 1 4 C(23) C -0.51915(6) 0.168594(16) -0.31167(6) 0.016 1 4 C(24) C -0.63253(6) 0.201016(17) -0.43698(6) 0.016 1 4 C(25) C -0.56237(6) 0.235252(16) -0.50568(6) 0.016 1 4 C(26) C -0.37967(6) 0.237352(15) -0.44724(6) 0.015 1 4 C(27) C -0.33541(6) 0.170370(15) -0.25384(6) 0.013 1 4 H(3) H -0.057113 0.12617 -0.379441 0.027 1 4 H(4) H 0.181858 0.06842 -0.216183 0.027 1 4 H(6) H 0.421214 0.150559 0.28885 0.028 1 4 H(7) H 0.192375 0.210842 0.119597 0.029 1 4 H(9) H 0.140627 0.047171 0.11177 0.027 1 4 H(10) H 0.080589 -0.026858 0.215096 0.031 1 4 H(11) H 0.322428 -0.083417 0.357282 0.034 1 4 H(12) H 0.625937 -0.065505 0.388354 0.032 1 4 H(14) H 1.038797 0.032195 0.398929 0.03 1 4 H(15) H 1.143539 0.108539 0.360783 0.032 1 4 H(16) H 0.914865 0.17069 0.219553 0.033 1 4 H(17) H 0.603992 0.156236 0.119357 0.029 1 4 H(23) H -0.574191 0.142963 -0.254864 0.028 1 4 H(24) H -0.77513 0.200161 -0.480813 0.029 1 4 H(25) H -0.650982 0.259951 -0.606559 0.031 1 4 H(26) H -0.324117 0.264098 -0.498179 0.032 1 4 H(27) H -0.248956 0.145353 -0.15301 0.027 1 4 # Anisotropic displacement parameters loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.01449 0.01478 0.04193 -0.00087 0.00755 0.01033 O(13) 0.01217 0.01204 0.02789 0.003 0.0095 0.00269 N(8) 0.00892 0.01106 0.02086 0.00215 0.00525 0.00441 C(1) 0.01099 0.01166 0.01924 0.00133 0.00521 0.00344 C(2) 0.01009 0.01104 0.01545 0.00131 0.00489 0.00213 C(3) 0.01141 0.013 0.01425 0.00131 0.00396 0.00085 C(4) 0.01147 0.01208 0.01528 0.00134 0.00499 0.00021 C(5) 0.00982 0.01125 0.01481 0.00175 0.00486 0.00199 C(6) 0.01197 0.01342 0.0141 0.00194 0.00392 0.00044 C(7) 0.01242 0.01213 0.01576 0.00175 0.00456 -0.00005 C(9) 0.01085 0.01359 0.01719 -0.00004 0.00511 0.00092 C(10) 0.01446 0.0142 0.01944 -0.00202 0.00671 0.00049 C(11) 0.01823 0.01142 0.02139 -0.00128 0.00824 0.00064 C(12) 0.01652 0.01077 0.0201 0.00179 0.00747 0.00142 C(14) 0.0107 0.0173 0.019 0.00234 0.00647 0.00141 C(15) 0.0111 0.0199 0.01939 -0.00027 0.00662 0.00125 C(16) 0.01289 0.01693 0.01828 -0.00108 0.00672 0.00242 C(17) 0.01181 0.01457 0.01783 0.00057 0.00607 0.0034 C(18) 0.00945 0.01309 0.01417 0.00152 0.00501 0.00168 C(19) 0.01104 0.01222 0.01585 0.00204 0.00618 0.00124 C(20) 0.01088 0.01055 0.01397 0.00105 0.00482 0.00063 C(21) 0.01174 0.01112 0.01588 0.00168 0.00578 0.00042 C(22) 0.01058 0.01099 0.01426 0.00129 0.00473 0.00135 C(23) 0.01334 0.01583 0.01827 -0.00161 0.00715 0.00012 C(24) 0.0114 0.0187 0.01778 0.00058 0.00557 -0.00118 C(25) 0.01234 0.01655 0.01592 0.00367 0.00425 0.00149 C(26) 0.01274 0.01343 0.01636 0.00264 0.00562 0.00351 C(27) 0.01284 0.01138 0.01501 0.00029 0.00563 0.00131 H(3) 0.023461 0.029612 0.021569 0.001151 0.003759 -0.0011 H(4) 0.02889 0.022415 0.028567 0.002894 0.01082 -0.0053 H(6) 0.023823 0.027034 0.022959 0.002359 0.002633 -0.002219 H(7) 0.029101 0.019485 0.032723 0.002945 0.008258 -0.005299 H(9) 0.021961 0.021716 0.036362 0.006331 0.012489 0.006226 H(10) 0.020809 0.028469 0.042949 -0.000687 0.014634 0.00718 H(11) 0.030659 0.020919 0.047618 0.000255 0.015741 0.011356 H(12) 0.024907 0.023185 0.043793 0.008471 0.012443 0.007881 H(14) 0.022776 0.026637 0.038119 0.008387 0.011705 0.006992 H(15) 0.016293 0.035743 0.041601 0.000238 0.011083 0.006407 H(16) 0.02488 0.024719 0.044702 -0.00254 0.013084 0.008844 H(17) 0.021501 0.022725 0.039272 0.005088 0.010224 0.007816 H(23) 0.02408 0.029824 0.031291 -0.000596 0.013684 0.007875 H(24) 0.016512 0.035786 0.033313 0.003042 0.009453 0.005632 H(25) 0.023506 0.029669 0.034849 0.00754 0.008025 0.012305 H(26) 0.025787 0.026689 0.040805 -0.000692 0.013101 0.011605 H(27) 0.021934 0.025448 0.029205 0.005391 0.008257 0.008862 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(1) 1.2249(6) 1_555 1_555 yes O(13) C(19) 1.3796(6) 1_555 1_555 yes O(13) C(21) 1.3803(5) 1_555 1_555 yes N(8) C(5) 1.4242(5) 1_555 1_555 yes N(8) C(18) 1.4045(5) 1_555 1_555 yes N(8) C(20) 1.4049(6) 1_555 1_555 yes C(1) C(2) 1.4962(6) 1_555 1_555 yes C(1) C(22) 1.4843(6) 1_555 1_555 yes C(2) C(3) 1.3967(6) 1_555 1_555 yes C(2) C(7) 1.3941(6) 1_555 1_555 yes C(3) C(4) 1.3923(6) 1_555 1_555 yes C(3) H(3) 1.0830(4) 1_555 1_555 yes C(4) C(5) 1.3948(5) 1_555 1_555 yes C(4) H(4) 1.0830(4) 1_555 1_555 yes C(5) C(6) 1.3953(6) 1_555 1_555 yes C(6) C(7) 1.3900(6) 1_555 1_555 yes C(6) H(6) 1.0830(4) 1_555 1_555 yes C(7) H(7) 1.0830(4) 1_555 1_555 yes C(9) C(10) 1.3960(6) 1_555 1_555 yes C(9) C(20) 1.3943(6) 1_555 1_555 yes C(9) H(9) 1.0830(4) 1_555 1_555 yes C(10) C(11) 1.3857(7) 1_555 1_555 yes C(10) H(10) 1.0830(5) 1_555 1_555 yes C(11) C(12) 1.3927(7) 1_555 1_555 yes C(11) H(11) 1.0830(5) 1_555 1_555 yes C(12) C(21) 1.3811(6) 1_555 1_555 yes C(12) H(12) 1.0830(4) 1_555 1_555 yes C(14) C(15) 1.3942(7) 1_555 1_555 yes C(14) C(19) 1.3825(6) 1_555 1_555 yes C(14) H(14) 1.0830(5) 1_555 1_555 yes C(15) C(16) 1.3864(7) 1_555 1_555 yes C(15) H(15) 1.0830(4) 1_555 1_555 yes C(16) C(17) 1.3961(6) 1_555 1_555 yes C(16) H(16) 1.0830(5) 1_555 1_555 yes C(17) C(18) 1.3972(6) 1_555 1_555 yes C(17) H(17) 1.0830(4) 1_555 1_555 yes C(18) C(19) 1.4032(6) 1_555 1_555 yes C(20) C(21) 1.3981(6) 1_555 1_555 yes C(22) C(26) 1.4001(6) 1_555 1_555 yes C(22) C(27) 1.3962(6) 1_555 1_555 yes C(23) C(24) 1.3907(7) 1_555 1_555 yes C(23) C(27) 1.3941(6) 1_555 1_555 yes C(23) H(23) 1.0830(5) 1_555 1_555 yes C(24) C(25) 1.3969(7) 1_555 1_555 yes C(24) H(24) 1.0830(5) 1_555 1_555 yes C(25) C(26) 1.3853(6) 1_555 1_555 yes C(25) H(25) 1.0830(4) 1_555 1_555 yes C(26) H(26) 1.0830(4) 1_555 1_555 yes C(27) H(27) 1.0830(4) 1_555 1_555 yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(19) O(13) C(21) 117.08(3) 1_555 1_555 1_555 yes C(5) N(8) C(18) 120.97(4) 1_555 1_555 1_555 yes C(5) N(8) C(20) 119.99(4) 1_555 1_555 1_555 yes C(18) N(8) C(20) 118.43(3) 1_555 1_555 1_555 yes O(1) C(1) C(2) 119.00(4) 1_555 1_555 1_555 yes O(1) C(1) C(22) 120.79(4) 1_555 1_555 1_555 yes C(2) C(1) C(22) 120.18(4) 1_555 1_555 1_555 yes C(1) C(2) C(3) 121.49(4) 1_555 1_555 1_555 yes C(1) C(2) C(7) 118.65(4) 1_555 1_555 1_555 yes C(3) C(2) C(7) 119.68(4) 1_555 1_555 1_555 yes C(2) C(3) C(4) 120.07(4) 1_555 1_555 1_555 yes C(2) C(3) H(3) 119.61(4) 1_555 1_555 1_555 yes C(4) C(3) H(3) 120.18(4) 1_555 1_555 1_555 yes C(3) C(4) C(5) 119.99(4) 1_555 1_555 1_555 yes C(3) C(4) H(4) 121.32(4) 1_555 1_555 1_555 yes C(5) C(4) H(4) 118.69(4) 1_555 1_555 1_555 yes N(8) C(5) C(4) 119.64(4) 1_555 1_555 1_555 yes N(8) C(5) C(6) 120.53(4) 1_555 1_555 1_555 yes C(4) C(5) C(6) 119.83(4) 1_555 1_555 1_555 yes C(5) C(6) C(7) 120.03(4) 1_555 1_555 1_555 yes C(5) C(6) H(6) 118.28(4) 1_555 1_555 1_555 yes C(7) C(6) H(6) 121.69(4) 1_555 1_555 1_555 yes C(2) C(7) C(6) 120.19(4) 1_555 1_555 1_555 yes C(2) C(7) H(7) 119.02(4) 1_555 1_555 1_555 yes C(6) C(7) H(7) 120.78(4) 1_555 1_555 1_555 yes C(10) C(9) C(20) 120.62(4) 1_555 1_555 1_555 yes C(10) C(9) H(9) 120.23(4) 1_555 1_555 1_555 yes C(20) C(9) H(9) 119.06(4) 1_555 1_555 1_555 yes C(9) C(10) C(11) 120.47(4) 1_555 1_555 1_555 yes C(9) C(10) H(10) 119.33(4) 1_555 1_555 1_555 yes C(11) C(10) H(10) 120.06(4) 1_555 1_555 1_555 yes C(10) C(11) C(12) 119.34(4) 1_555 1_555 1_555 yes C(10) C(11) H(11) 120.15(5) 1_555 1_555 1_555 yes C(12) C(11) H(11) 120.43(4) 1_555 1_555 1_555 yes C(11) C(12) C(21) 120.00(4) 1_555 1_555 1_555 yes C(11) C(12) H(12) 121.00(4) 1_555 1_555 1_555 yes C(21) C(12) H(12) 119.00(4) 1_555 1_555 1_555 yes C(15) C(14) C(19) 120.14(4) 1_555 1_555 1_555 yes C(15) C(14) H(14) 122.33(4) 1_555 1_555 1_555 yes C(19) C(14) H(14) 117.53(4) 1_555 1_555 1_555 yes C(14) C(15) C(16) 119.38(4) 1_555 1_555 1_555 yes C(14) C(15) H(15) 119.06(4) 1_555 1_555 1_555 yes C(16) C(15) H(15) 121.56(5) 1_555 1_555 1_555 yes C(15) C(16) C(17) 120.20(4) 1_555 1_555 1_555 yes C(15) C(16) H(16) 121.82(4) 1_555 1_555 1_555 yes C(17) C(16) H(16) 117.97(4) 1_555 1_555 1_555 yes C(16) C(17) C(18) 121.19(4) 1_555 1_555 1_555 yes C(16) C(17) H(17) 116.82(4) 1_555 1_555 1_555 yes C(18) C(17) H(17) 121.99(4) 1_555 1_555 1_555 yes N(8) C(18) C(17) 123.68(4) 1_555 1_555 1_555 yes N(8) C(18) C(19) 118.79(4) 1_555 1_555 1_555 yes C(17) C(18) C(19) 117.51(4) 1_555 1_555 1_555 yes O(13) C(19) C(14) 116.40(4) 1_555 1_555 1_555 yes O(13) C(19) C(18) 122.01(4) 1_555 1_555 1_555 yes C(14) C(19) C(18) 121.56(4) 1_555 1_555 1_555 yes N(8) C(20) C(9) 122.65(4) 1_555 1_555 1_555 yes N(8) C(20) C(21) 119.29(4) 1_555 1_555 1_555 yes C(9) C(20) C(21) 118.02(4) 1_555 1_555 1_555 yes O(13) C(21) C(12) 116.76(4) 1_555 1_555 1_555 yes O(13) C(21) C(20) 121.70(4) 1_555 1_555 1_555 yes C(12) C(21) C(20) 121.54(4) 1_555 1_555 1_555 yes C(1) C(22) C(26) 119.01(4) 1_555 1_555 1_555 yes C(1) C(22) C(27) 121.04(4) 1_555 1_555 1_555 yes C(26) C(22) C(27) 119.72(4) 1_555 1_555 1_555 yes C(24) C(23) C(27) 120.03(4) 1_555 1_555 1_555 yes C(24) C(23) H(23) 119.36(4) 1_555 1_555 1_555 yes C(27) C(23) H(23) 120.55(4) 1_555 1_555 1_555 yes C(23) C(24) C(25) 119.98(4) 1_555 1_555 1_555 yes C(23) C(24) H(24) 120.47(4) 1_555 1_555 1_555 yes C(25) C(24) H(24) 119.54(4) 1_555 1_555 1_555 yes C(24) C(25) C(26) 120.15(4) 1_555 1_555 1_555 yes C(24) C(25) H(25) 120.05(4) 1_555 1_555 1_555 yes C(26) C(25) H(25) 119.79(4) 1_555 1_555 1_555 yes C(22) C(26) C(25) 120.08(4) 1_555 1_555 1_555 yes C(22) C(26) H(26) 119.37(4) 1_555 1_555 1_555 yes C(25) C(26) H(26) 120.54(4) 1_555 1_555 1_555 yes C(22) C(27) C(23) 120.02(4) 1_555 1_555 1_555 yes C(22) C(27) H(27) 121.06(4) 1_555 1_555 1_555 yes C(23) C(27) H(27) 118.88(4) 1_555 1_555 1_555 yes 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 C(19) O(13) C(21) C(12) -164.64(6) 1_555 1_555 1_555 1_555 yes C(21) O(13) C(19) C(14) 167.90(6) 1_555 1_555 1_555 1_555 yes C(21) O(13) C(19) C(18) -14.36(4) 1_555 1_555 1_555 1_555 yes C(19) O(13) C(21) C(20) 14.82(4) 1_555 1_555 1_555 1_555 yes C(18) N(8) C(5) C(4) 121.62(5) 1_555 1_555 1_555 1_555 yes C(18) N(8) C(5) C(6) -58.41(4) 1_555 1_555 1_555 1_555 yes C(5) N(8) C(18) C(17) 1.05(4) 1_555 1_555 1_555 1_555 yes C(5) N(8) C(18) C(19) -177.02(6) 1_555 1_555 1_555 1_555 yes C(20) N(8) C(5) C(4) -67.46(4) 1_555 1_555 1_555 1_555 yes C(20) N(8) C(5) C(6) 112.50(5) 1_555 1_555 1_555 1_555 yes C(5) N(8) C(20) C(9) -5.12(4) 1_555 1_555 1_555 1_555 yes C(5) N(8) C(20) C(21) 177.34(6) 1_555 1_555 1_555 1_555 yes C(18) N(8) C(20) C(9) 166.02(6) 1_555 1_555 1_555 1_555 yes C(20) N(8) C(18) C(17) -170.01(6) 1_555 1_555 1_555 1_555 yes C(20) N(8) C(18) C(19) 11.93(4) 1_555 1_555 1_555 1_555 yes C(18) N(8) C(20) C(21) -11.51(4) 1_555 1_555 1_555 1_555 yes O(1) C(1) C(2) C(3) -119.95(6) 1_555 1_555 1_555 1_555 yes O(1) C(1) C(2) C(7) 55.13(5) 1_555 1_555 1_555 1_555 yes O(1) C(1) C(22) C(26) 13.96(4) 1_555 1_555 1_555 1_555 yes O(1) C(1) C(22) C(27) -160.44(6) 1_555 1_555 1_555 1_555 yes C(22) C(1) C(2) C(3) 61.88(5) 1_555 1_555 1_555 1_555 yes C(22) C(1) C(2) C(7) -123.04(5) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(22) C(26) -167.91(6) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(22) C(27) 17.70(4) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(4) 170.57(6) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) H(3) -5.02(4) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(7) C(6) -173.76(6) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(7) H(7) 7.38(4) 1_555 1_555 1_555 1_555 yes C(7) C(2) C(3) C(4) -4.46(4) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(7) C(6) 1.42(4) 1_555 1_555 1_555 1_555 yes C(7) C(2) C(3) H(3) 179.95(6) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(7) H(7) -177.44(6) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) C(5) 3.19(4) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) H(4) -176.18(6) 1_555 1_555 1_555 1_555 yes H(3) C(3) C(4) C(5) 178.76(6) 1_555 1_555 1_555 1_555 yes H(3) C(3) C(4) H(4) -0.61(4) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(5) N(8) -178.92(6) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(5) C(6) 1.12(4) 1_555 1_555 1_555 1_555 yes H(4) C(4) C(5) N(8) 0.47(4) 1_555 1_555 1_555 1_555 yes H(4) C(4) C(5) C(6) -179.49(6) 1_555 1_555 1_555 1_555 yes N(8) C(5) C(6) C(7) 175.88(6) 1_555 1_555 1_555 1_555 yes N(8) C(5) C(6) H(6) -4.25(4) 1_555 1_555 1_555 1_555 yes C(4) C(5) C(6) C(7) -4.16(4) 1_555 1_555 1_555 1_555 yes C(4) C(5) C(6) H(6) 175.72(6) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(7) C(2) 2.89(4) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(7) H(7) -178.27(6) 1_555 1_555 1_555 1_555 yes H(6) C(6) C(7) C(2) -176.98(7) 1_555 1_555 1_555 1_555 yes H(6) C(6) C(7) H(7) 1.86(4) 1_555 1_555 1_555 1_555 yes C(10) C(9) C(20) N(8) -178.07(6) 1_555 1_555 1_555 1_555 yes C(20) C(9) C(10) C(11) 0.92(4) 1_555 1_555 1_555 1_555 yes C(10) C(9) C(20) C(21) -0.50(4) 1_555 1_555 1_555 1_555 yes C(20) C(9) C(10) H(10) 176.68(7) 1_555 1_555 1_555 1_555 yes H(9) C(9) C(10) C(11) -175.71(7) 1_555 1_555 1_555 1_555 yes H(9) C(9) C(10) H(10) 0.04(4) 1_555 1_555 1_555 1_555 yes H(9) C(9) C(20) N(8) -1.39(4) 1_555 1_555 1_555 1_555 yes H(9) C(9) C(20) C(21) 176.17(6) 1_555 1_555 1_555 1_555 yes C(9) C(10) C(11) C(12) -0.57(4) 1_555 1_555 1_555 1_555 yes C(9) C(10) C(11) H(11) 176.44(7) 1_555 1_555 1_555 1_555 yes H(10) C(10) C(11) C(12) -176.29(7) 1_555 1_555 1_555 1_555 yes H(10) C(10) C(11) H(11) 0.72(4) 1_555 1_555 1_555 1_555 yes C(10) C(11) C(12) C(21) -0.19(4) 1_555 1_555 1_555 1_555 yes C(10) C(11) C(12) H(12) 179.56(7) 1_555 1_555 1_555 1_555 yes H(11) C(11) C(12) C(21) -177.19(7) 1_555 1_555 1_555 1_555 yes H(11) C(11) C(12) H(12) 2.57(4) 1_555 1_555 1_555 1_555 yes C(11) C(12) C(21) O(13) -179.92(6) 1_555 1_555 1_555 1_555 yes C(11) C(12) C(21) C(20) 0.62(4) 1_555 1_555 1_555 1_555 yes H(12) C(12) C(21) O(13) 0.32(4) 1_555 1_555 1_555 1_555 yes H(12) C(12) C(21) C(20) -179.14(7) 1_555 1_555 1_555 1_555 yes C(15) C(14) C(19) O(13) 176.20(6) 1_555 1_555 1_555 1_555 yes C(19) C(14) C(15) C(16) 1.38(4) 1_555 1_555 1_555 1_555 yes C(15) C(14) C(19) C(18) -1.54(4) 1_555 1_555 1_555 1_555 yes C(19) C(14) C(15) H(15) -178.10(7) 1_555 1_555 1_555 1_555 yes H(14) C(14) C(15) C(16) -178.77(7) 1_555 1_555 1_555 1_555 yes H(14) C(14) C(15) H(15) 1.75(4) 1_555 1_555 1_555 1_555 yes H(14) C(14) C(19) O(13) -3.66(4) 1_555 1_555 1_555 1_555 yes H(14) C(14) C(19) C(18) 178.60(7) 1_555 1_555 1_555 1_555 yes C(14) C(15) C(16) C(17) -0.26(4) 1_555 1_555 1_555 1_555 yes C(14) C(15) C(16) H(16) -179.94(7) 1_555 1_555 1_555 1_555 yes H(15) C(15) C(16) C(17) 179.20(7) 1_555 1_555 1_555 1_555 yes H(15) C(15) C(16) H(16) -0.47(4) 1_555 1_555 1_555 1_555 yes C(15) C(16) C(17) C(18) -0.72(4) 1_555 1_555 1_555 1_555 yes C(15) C(16) C(17) H(17) -179.91(7) 1_555 1_555 1_555 1_555 yes H(16) C(16) C(17) C(18) 178.97(7) 1_555 1_555 1_555 1_555 yes H(16) C(16) C(17) H(17) -0.23(4) 1_555 1_555 1_555 1_555 yes C(16) C(17) C(18) N(8) -177.51(7) 1_555 1_555 1_555 1_555 yes C(16) C(17) C(18) C(19) 0.57(4) 1_555 1_555 1_555 1_555 yes H(17) C(17) C(18) N(8) 1.64(4) 1_555 1_555 1_555 1_555 yes H(17) C(17) C(18) C(19) 179.73(6) 1_555 1_555 1_555 1_555 yes N(8) C(18) C(19) O(13) 1.12(4) 1_555 1_555 1_555 1_555 yes N(8) C(18) C(19) C(14) 178.74(6) 1_555 1_555 1_555 1_555 yes C(17) C(18) C(19) O(13) -177.06(6) 1_555 1_555 1_555 1_555 yes C(17) C(18) C(19) C(14) 0.56(4) 1_555 1_555 1_555 1_555 yes N(8) C(20) C(21) O(13) -2.06(4) 1_555 1_555 1_555 1_555 yes N(8) C(20) C(21) C(12) 177.38(6) 1_555 1_555 1_555 1_555 yes C(9) C(20) C(21) O(13) -179.71(6) 1_555 1_555 1_555 1_555 yes C(9) C(20) C(21) C(12) -0.27(4) 1_555 1_555 1_555 1_555 yes C(1) C(22) C(26) C(25) -173.96(6) 1_555 1_555 1_555 1_555 yes C(1) C(22) C(26) H(26) 5.55(4) 1_555 1_555 1_555 1_555 yes C(1) C(22) C(27) C(23) 173.29(6) 1_555 1_555 1_555 1_555 yes C(1) C(22) C(27) H(27) -4.29(4) 1_555 1_555 1_555 1_555 yes C(26) C(22) C(27) C(23) -1.06(4) 1_555 1_555 1_555 1_555 yes C(27) C(22) C(26) C(25) 0.51(4) 1_555 1_555 1_555 1_555 yes C(27) C(22) C(26) H(26) -179.99(6) 1_555 1_555 1_555 1_555 yes C(26) C(22) C(27) H(27) -178.64(6) 1_555 1_555 1_555 1_555 yes C(24) C(23) C(27) C(22) 0.65(4) 1_555 1_555 1_555 1_555 yes C(27) C(23) C(24) C(25) 0.31(4) 1_555 1_555 1_555 1_555 yes C(27) C(23) C(24) H(24) -179.05(7) 1_555 1_555 1_555 1_555 yes C(24) C(23) C(27) H(27) 178.29(7) 1_555 1_555 1_555 1_555 yes H(23) C(23) C(24) C(25) 177.63(7) 1_555 1_555 1_555 1_555 yes H(23) C(23) C(24) H(24) -1.74(4) 1_555 1_555 1_555 1_555 yes H(23) C(23) C(27) C(22) -176.63(7) 1_555 1_555 1_555 1_555 yes H(23) C(23) C(27) H(27) 1.01(4) 1_555 1_555 1_555 1_555 yes C(23) C(24) C(25) C(26) -0.87(4) 1_555 1_555 1_555 1_555 yes C(23) C(24) C(25) H(25) 178.20(7) 1_555 1_555 1_555 1_555 yes H(24) C(24) C(25) C(26) 178.51(7) 1_555 1_555 1_555 1_555 yes H(24) C(24) C(25) H(25) -2.42(4) 1_555 1_555 1_555 1_555 yes C(24) C(25) C(26) C(22) 0.45(4) 1_555 1_555 1_555 1_555 yes C(24) C(25) C(26) H(26) -179.05(7) 1_555 1_555 1_555 1_555 yes H(25) C(25) C(26) C(22) -178.62(7) 1_555 1_555 1_555 1_555 yes H(25) C(25) C(26) H(26) 1.88(4) 1_555 1_555 1_555 1_555 yes # Multipole parameters loop_ _atom_rho_multipole_atom_label _atom_rho_multipole_coeff_Pv _atom_rho_multipole_coeff_P00 _atom_rho_multipole_coeff_P11 _atom_rho_multipole_coeff_P1-1 _atom_rho_multipole_coeff_P10 _atom_rho_multipole_coeff_P20 _atom_rho_multipole_coeff_P21 _atom_rho_multipole_coeff_P2-1 _atom_rho_multipole_coeff_P22 _atom_rho_multipole_coeff_P2-2 _atom_rho_multipole_coeff_P30 _atom_rho_multipole_coeff_P31 _atom_rho_multipole_coeff_P3-1 _atom_rho_multipole_coeff_P32 _atom_rho_multipole_coeff_P3-2 _atom_rho_multipole_coeff_P33 _atom_rho_multipole_coeff_P3-3 _atom_rho_multipole_coeff_P40 _atom_rho_multipole_coeff_P41 _atom_rho_multipole_coeff_P4-1 _atom_rho_multipole_coeff_P42 _atom_rho_multipole_coeff_P4-2 _atom_rho_multipole_coeff_P43 _atom_rho_multipole_coeff_P4-3 _atom_rho_multipole_coeff_P44 _atom_rho_multipole_coeff_P4-4 _atom_rho_multipole_kappa _atom_rho_multipole_kappa_prime0 _atom_rho_multipole_kappa_prime1 _atom_rho_multipole_kappa_prime2 _atom_rho_multipole_kappa_prime3 _atom_rho_multipole_kappa_prime4 O(1) 5.8899 0 0.0139 0.0017 -0.0544 0.0106 0.0171 0.0031 -0.0248 -0.0054 -0.028 0.0079 -0.0311 0.097 -0.0283 0.0005 -0.0088 0.0062 0.0463 0.0174 0.0149 -0.0043 0.0031 0.0316 0.0728 0.0056 0.989071 0.9891 0.9891 0.9891 0.9891 0.9891 O(13) 5.9601 0 0.0021 -0.0502 -0.0016 -0.0132 0.0092 0.0002 0.0012 0.0091 0.0609 -0.0091 -0.0178 0.0535 -0.0171 -0.0146 -0.0118 0.0294 -0.0071 0.0072 0.0111 0.0273 -0.0196 0.0058 0.0136 -0.0048 0.989071 0.9891 0.9891 0.9891 0.9891 0.9891 N(8) 4.8538 0 0.0118 -0.0438 0.0007 -0.0087 0.0264 0.0255 0.0323 0.0453 0.1857 0.0005 -0.0145 0.1162 0.0003 0.0133 0.0024 0.0503 0.0544 0.0213 -0.0253 0.0618 0.025 0.0024 0.0522 0.0106 0.988201 0.858159 0.858159 0.858159 0.858159 0.858159 C(1) 4.2014 0 -0.0494 -0.0223 0.1348 0.1798 0.0058 0.0341 -0.1404 0.0455 0.4945 -0.0225 0.0356 0.3086 0.0016 -0.0373 0.0261 -0.0753 -0.056 0.0127 -0.0878 -0.1424 0.0328 -0.022 0.0285 -0.0944 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(2) 4.0289 0 0.015 0.1725 0.0039 0.0671 0.014 -0.0444 -0.1169 -0.0289 0.2929 -0.0087 0.0542 0.2301 -0.0321 0.022 -0.0556 -0.0548 -0.0309 0.0021 -0.0447 -0.1099 0.0491 0.0995 -0.0247 -0.05 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(3) 4.196 0 0.0094 0.0758 0.0155 0.1216 0.0086 0.0287 -0.1583 -0.0078 0.3385 0.049 0.0365 0.18 0.0014 -0.0035 -0.0383 0.0842 0.0016 0.0321 0.0093 -0.035 0.0091 0.0192 -0.0392 0.0015 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(4) 4.3161 0 -0.0544 -0.021 0.0739 0.1512 0.0197 0.0027 -0.1613 -0.0006 0.3286 -0.0074 0.0779 0.1973 0.003 0.0045 0.0086 0.143 -0.0398 0.0449 0.0029 -0.0246 -0.0347 -0.0538 -0.0037 0.013 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(5) 4.1741 0 -0.0226 0.0597 0.0993 0.128 0.0116 -0.0641 -0.0779 0.0315 0.3073 0.0179 -0.062 0.2312 0.0903 0.005 0.0323 0.0484 -0.0029 -0.0442 -0.0292 0.0336 -0.0573 0.0395 -0.0096 0.0205 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(6) 4.1894 0 -0.0957 0.0508 0.0167 0.102 0.0562 -0.0095 -0.1549 -0.039 0.2922 -0.0686 0.0689 0.2101 0.0289 -0.0334 -0.0152 0.0713 0.0219 0.0252 -0.0682 0.054 -0.0088 0.0358 -0.0012 0.0279 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(7) 4.2542 0 -0.0133 -0.0108 0.0863 0.0925 0.0112 -0.0157 -0.196 0.0111 0.3194 -0.0066 0.0689 0.2194 0.0899 0.038 0.0458 0.0834 -0.0577 -0.0599 0.0145 -0.0602 -0.0524 -0.0792 0.0196 -0.0102 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(9) 4.0907 0 -0.0556 -0.0769 0.0576 0.0913 0.0425 0.0773 -0.1565 -0.0271 0.352 -0.0133 -0.0415 0.1445 -0.0403 0.0097 0.045 0.0494 0.0211 0.0316 0.0466 0.0681 0.002 -0.0423 0.1047 -0.0531 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(10) 4.1701 0 -0.0475 0.002 0.0232 0.1464 0.0036 -0.0004 -0.1358 0.0359 0.3664 -0.0464 -0.0036 0.1693 -0.0169 0.0131 -0.0197 0.1744 -0.0806 -0.1 0.0369 0.0164 -0.0935 -0.0589 -0.005 -0.0274 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(11) 4.2823 0 -0.069 0.0941 0.1055 0.1424 -0.0005 0.0058 -0.1524 0.0156 0.3947 -0.0797 -0.0263 0.184 0.0273 -0.0702 -0.0416 0.1433 -0.1028 0.0009 0.0258 0.0337 -0.0762 0.0271 0.0634 0.0403 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(12) 4.3786 0 -0.0064 -0.0716 0.0121 0.0692 0.0214 0.0738 -0.2139 0.0011 0.3948 -0.0152 -0.0789 0.2019 -0.0445 0.0362 0.0371 0.1042 -0.0395 0.0155 -0.0058 -0.0276 -0.0404 0.0032 0.0901 0.0888 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(14) 4.193 0 0.0035 -0.0214 0.0238 0.1444 -0.0248 0.0361 -0.1749 0.0201 0.2366 -0.0118 0.0127 0.1428 -0.0652 0.0264 0.0324 0.0753 0.0312 -0.0581 -0.0447 0.0074 -0.0377 -0.0262 0.051 -0.0014 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(15) 4.2712 0 -0.0018 0.0429 -0.0133 0.1086 0.0634 0.0246 -0.1135 0.0251 0.371 -0.0588 0.0196 0.2084 -0.0423 0.0115 -0.0121 0.0714 0.0582 -0.0567 0.0344 0.0529 0.001 -0.0053 0.082 0.0297 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(16) 4.2875 0 -0.0044 -0.0233 0.1072 0.1076 -0.0039 -0.0204 -0.1494 -0.0683 0.3763 -0.0419 0.0731 0.2245 -0.0247 0.0061 0.0323 0.0969 0.0728 -0.0708 -0.0492 -0.0203 0.0038 -0.0279 0.0137 -0.0461 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(17) 4.2245 0 -0.0658 -0.015 0.0817 0.0915 0.0332 -0.0204 -0.1609 -0.0248 0.4019 -0.0257 0.0388 0.184 -0.0233 0.0175 0.0296 0.0467 0.048 -0.0597 0.0001 0.0517 0.01 -0.0758 0.0521 -0.0427 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(18) 4.0985 0 0.0164 0.0402 -0.0328 0.1195 0.0245 -0.0007 -0.0956 -0.0511 0.3624 0.0116 0.0551 0.2891 0.0028 0.0267 0.0927 -0.1463 0.1022 0.0195 -0.1414 0.0625 -0.0892 -0.0081 -0.0045 -0.001 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(19) 4.2296 0 0.0063 -0.0557 0.1094 0.1376 -0.0369 0.015 -0.1305 -0.0097 0.3266 0.0022 0.0259 0.3436 0.0064 0.0062 -0.022 0.1906 -0.0226 0.0968 0.0693 0.057 -0.0257 0.0252 0.0936 0.0157 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(20) 4.2796 0 0.0273 0.058 0.1177 0.1984 -0.0251 0.0003 -0.0953 0.0209 0.3895 -0.0246 0.0087 0.2756 -0.03 0.0346 -0.0132 0.082 -0.022 -0.0385 -0.0223 0.0086 -0.0917 -0.0438 -0.0409 0.0333 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(21) 4.2402 0 0.0744 -0.1103 0.0793 0.1597 -0.0044 -0.0276 -0.1159 0.0131 0.3111 0.0091 -0.0233 0.2367 0.021 0.0266 -0.0145 0.036 0.0251 0.0551 -0.0192 0.1021 -0.0437 0.0511 0.0386 0.0408 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(22) 4.1148 0 0.0597 0.1603 0.0851 0.1321 0.0121 0.0536 -0.1286 0.0115 0.4247 0.0617 -0.0151 0.2271 0.0765 0.0101 0.0068 0.077 0.0292 0.1024 0.0537 -0.1122 0.0447 -0.0354 0.1 0.0013 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(23) 4.1308 0 -0.0289 -0.0787 0.0396 0.1532 0.0522 0.032 -0.1147 0.0065 0.406 -0.0549 -0.0046 0.1654 0.0388 -0.0079 0.0021 0.0372 -0.0455 -0.1194 0.0233 0.018 -0.0332 -0.0823 0.0001 0.04 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(24) 4.3245 0 0.0212 0.0766 -0.0116 0.1639 -0.0377 0.0513 -0.2051 -0.107 0.3779 -0.035 -0.0795 0.2395 0.0845 0.024 0.0199 0.0905 -0.0159 0.069 -0.0579 -0.1344 -0.0056 0.028 0.0511 0.0273 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(25) 4.1236 0 0.0485 -0.0015 0.0597 0.0406 -0.0039 -0.0582 -0.1766 -0.0614 0.3676 0.0073 0.0447 0.1984 0.089 -0.0445 0.0063 0.0797 0.0332 -0.0102 -0.0114 -0.0103 0.0393 0.0756 0.0221 -0.0041 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(26) 4.1453 0 -0.0132 -0.0573 0.1123 0.0912 0.0516 -0.0399 -0.192 -0.0048 0.3062 0.0197 0.0652 0.1862 0.0446 -0.0056 0.0097 -0.0183 0.0727 0.0496 0.0613 -0.0871 0.0185 0.0513 0.0589 -0.0213 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 C(27) 3.9679 0 -0.0228 0.007 0.1237 0.0994 0.0167 -0.0143 -0.1894 0.0742 0.295 0.0231 0.081 0.164 -0.0083 0.0272 -0.035 0.1058 0.001 -0.0056 0.0407 -0.0625 -0.0524 0.0524 0.0408 0.0043 0.957424 0.822955 0.822955 0.822955 0.822955 0.822955 H(3) 0.7505 0 -0.0416 0.0282 0.138 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 H(4) 0.7051 0 -0.021 -0.0115 0.1247 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 H(6) 0.7734 0 0.0505 -0.0078 0.1252 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 H(7) 0.7429 0 -0.002 -0.0132 0.1185 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 H(9) 0.7346 0 0.0425 -0.0006 0.1169 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 H(10) 0.682 0 0.0789 -0.0271 0.1033 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 H(11) 0.7017 0 0.0524 0.0234 0.1162 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 H(12) 0.72 0 0.0271 0.0271 0.1373 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 H(14) 0.7372 0 0.0266 0.021 0.1012 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 H(15) 0.721 0 -0.0095 -0.0482 0.1246 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 H(16) 0.7258 0 -0.0034 -0.003 0.0942 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 H(17) 0.7429 0 0.0258 -0.0052 0.1236 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 H(23) 0.6695 0 0.0143 0.0042 0.1283 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 H(24) 0.6871 0 -0.0184 -0.0049 0.132 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 H(25) 0.7374 0 0.0088 0.0231 0.1514 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 H(26) 0.8042 0 -0.0204 0.0207 0.12 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 H(27) 0.747 0 -0.0079 -0.0497 0.126 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29 1.29 1.29 1.29 1.29 loop_ _atom_local_axes_atom_label _atom_local_axes_atom0 _atom_local_axes_ax1 _atom_local_axes_atom1 _atom_local_axes_atom2 _atom_local_axes_ax2 O(1) C(1) Z O(1) C(2) Y O(13) C(21) Z O(13) C(19) Y N(8) C(20) Z N(8) C(18) Y C(1) O(1) Z C(1) C(22) Y C(2) C(7) Z C(2) C(3) Y C(3) H(3) Z C(3) C(4) Y C(4) H(4) Z C(4) C(3) Y C(5) C(6) Z C(5) C(4) Y C(6) H(6) Z C(6) C(7) Y C(7) H(7) Z C(7) C(6) Y C(9) H(9) Z C(9) C(20) Y C(10) H(10) Z C(10) C(11) Y C(11) H(11) Z C(11) C(10) Y C(12) H(12) Z C(12) C(21) Y C(14) H(14) Z C(14) C(19) Y C(15) H(15) Z C(15) C(16) Y C(16) H(16) Z C(16) C(15) Y C(17) H(17) Z C(17) C(16) Y C(18) C(17) Z C(18) C(19) Y C(19) C(14) Z C(19) O(13) Y C(20) C(9) Z C(20) C(21) Y C(21) C(12) Z C(21) O(13) Y C(22) C(27) Z C(22) C(26) Y C(23) H(23) Z C(23) C(24) Y C(24) H(24) Z C(24) C(23) Y C(25) H(25) Z C(25) C(26) Y C(26) H(26) Z C(26) C(25) Y C(27) H(27) Z C(27) C(23) Y H(3) C(3) Z H(3) C(2) Y H(4) C(4) Z H(4) C(3) Y H(6) C(6) Z H(6) C(5) Y H(7) C(7) Z H(7) C(6) Y H(9) C(9) Z H(9) C(20) Y H(10) C(10) Z H(10) C(9) Y H(11) C(11) Z H(11) C(12) Y H(12) C(12) Z H(12) C(21) Y H(14) C(14) Z H(14) C(19) Y H(15) C(15) Z H(15) C(14) Y H(16) C(16) Z H(16) C(17) Y H(17) C(17) Z H(17) C(16) Y H(23) C(23) Z H(23) C(24) Y H(24) C(24) Z H(24) C(23) Y H(25) C(25) Z H(25) C(24) Y H(26) C(26) Z H(26) C(22) Y H(27) C(27) Z H(27) C(23) Y