# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _audit_creation_date 'Mon Feb 16 13:49:24 2004' _audit_creation_method 'by teXsan' _audit_update_record ? _journal_coden_Cambridge 182 loop_ _publ_author_name 'Fumio Toda' 'Shinji Toyota' 'Kazuhiro Yoshizawa' _publ_contact_author_name 'Prof Fumio Toda' _publ_contact_author_address ; Chemistry Okayama Univ. of Science Ridai-cho 1-1 Okayama-shi Okayama 700-0005 JAPAN ; _publ_contact_author_email ' toda@chem.ous.ac.jp ' _publ_contact_author_fax ' +81-86-256-9604 ' _publ_contact_author_phone ' +81-86-256-9604 ' _publ_contact_letter ; ? ; _publ_requested_journal ' Chemical Communications' _publ_requested_category ' CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? _publ_section_title ; A novel transformation of a 1:1:1 racemic complex of 2,2f-dihydroxy-1,1f-binaphthyl, Me4NCl and MeOH into a conglomerate in the solid state by heating or contact with MeOH vapour ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation, Rigaku Corporation. (2000). teXsan. Single Crystal Structure Analysis Software. Version 1.11. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. ; #------------------------------------------------------------------------------ data_for_complex_of_BNO_and_Me4NCl _database_code_depnum_ccdc_archive 'CCDC 235218' #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C24 H26 Cl N O2 ' _chemical_formula_moiety ? _chemical_formula_weight 395.93 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z _cell_length_a 9.0002(1) _cell_length_b 14.1519(3) _cell_length_c 16.6811(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2124.67(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 31359 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 123.2 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.250 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Higashi, 1995)' _exptl_absorpt_correction_T_min 0.908 _exptl_absorpt_correction_T_max 0.952 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 16936 _diffrn_reflns_av_R_equivalents 0.023 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.9960 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.9960 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2759 _reflns_number_gt 2729 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1632 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 2759 _refine_ls_number_parameters 254 _refine_ls_goodness_of_fit_ref 2.269 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.07100(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0012 _refine_diff_density_max 0.56 _refine_diff_density_min -0.45 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack -0.10(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; Cl Cl 0.148 0.159 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; N N 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O O 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT 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_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl(1) Cl 0.46271(4) 0.78872(3) 0.13911(2) 0.0213(1) Uani 1.00 d . . . O(1) O 0.3250(1) 0.60038(8) 0.17961(8) 0.0177(3) Uani 1.00 d . . . O(2) O 0.2855(1) 0.39080(9) 0.26816(7) 0.0188(3) Uani 1.00 d . . . N(1) N 0.0995(2) 0.9181(1) 0.03342(9) 0.0268(4) Uani 1.00 d . . . C(1) C 0.1058(2) 0.5107(1) 0.17664(9) 0.0139(3) Uani 1.00 d . . . C(2) C 0.1758(2) 0.5950(1) 0.19283(9) 0.0146(3) Uani 1.00 d . . . C(3) C 0.0958(2) 0.6740(1) 0.22304(10) 0.0167(3) Uani 1.00 d . . . C(4) C -0.0548(2) 0.6672(1) 0.2351(1) 0.0171(3) Uani 1.00 d . . . C(5) C -0.1327(2) 0.5824(1) 0.21901(10) 0.0165(3) Uani 1.00 d . . . C(6) C -0.2885(2) 0.5742(1) 0.2303(1) 0.0181(4) Uani 1.00 d . . . C(7) C -0.3600(2) 0.4898(1) 0.2157(1) 0.0198(4) Uani 1.00 d . . . C(8) C -0.2803(2) 0.4112(1) 0.1877(1) 0.0192(4) Uani 1.00 d . . . C(9) C -0.1289(2) 0.4170(1) 0.17517(10) 0.0167(3) Uani 1.00 d . . . C(10) C -0.0497(2) 0.5030(1) 0.19054(9) 0.0138(3) Uani 1.00 d . . . C(11) C 0.1895(2) 0.4307(1) 0.14104(9) 0.0130(3) Uani 1.00 d . . . C(12) C 0.2801(2) 0.3736(1) 0.18799(10) 0.0148(3) Uani 1.00 d . . . C(13) C 0.3645(2) 0.2992(1) 0.15337(10) 0.0171(3) Uani 1.00 d . . . C(14) C 0.3555(2) 0.2813(1) 0.0730(1) 0.0190(3) Uani 1.00 d . . . C(15) C 0.2625(2) 0.3368(1) 0.0221(1) 0.0181(4) Uani 1.00 d . . . C(16) C 0.2551(2) 0.3222(1) -0.0619(1) 0.0240(4) Uani 1.00 d . . . C(17) C 0.1732(2) 0.3803(2) -0.1099(1) 0.0267(4) Uani 1.00 d . . . C(18) C 0.0913(2) 0.4567(1) -0.07579(10) 0.0215(4) Uani 1.00 d . . . C(19) C 0.0942(2) 0.4713(1) 0.00557(10) 0.0173(3) Uani 1.00 d . . . C(20) C 0.1801(2) 0.4124(1) 0.05707(9) 0.0139(3) Uani 1.00 d . . . C(21) C 0.0373(4) 0.8300(2) 0.0705(2) 0.0652(9) Uani 1.00 d . . . C(22) C 0.1651(3) 0.9752(2) 0.0969(2) 0.0548(7) Uani 1.00 d . . . C(23) C -0.0225(3) 0.9671(2) -0.0084(1) 0.0489(7) Uani 1.00 d . . . C(24) C 0.2166(2) 0.8884(2) -0.0240(1) 0.0330(5) Uani 1.00 d . . . H(1) H 0.3527 0.6620 0.1810 0.0325 Uiso 1.00 calc . . . H(2) H 0.1465 0.7312 0.2346 0.0203 Uiso 1.00 calc . . . H(3) H -0.1075 0.7208 0.2545 0.0208 Uiso 1.00 calc . . . H(4) H -0.3438 0.6271 0.2484 0.0225 Uiso 1.00 calc . . . H(5) H -0.4643 0.4852 0.2244 0.0238 Uiso 1.00 calc . . . H(6) H -0.3306 0.3533 0.1775 0.0227 Uiso 1.00 calc . . . H(7) H -0.0759 0.3631 0.1562 0.0195 Uiso 1.00 calc . . . H(8) H 0.3556 0.3605 0.2969 0.0325 Uiso 1.00 calc . . . H(9) H 0.4278 0.2621 0.1862 0.0201 Uiso 1.00 calc . . . H(10) H 0.4122 0.2315 0.0504 0.0226 Uiso 1.00 calc . . . H(11) H 0.3082 0.2713 -0.0853 0.0288 Uiso 1.00 calc . . . H(12) H 0.1692 0.3690 -0.1660 0.0309 Uiso 1.00 calc . . . H(13) H 0.0349 0.4973 -0.1094 0.0258 Uiso 1.00 calc . . . H(14) H 0.0388 0.5219 0.0278 0.0210 Uiso 1.00 calc . . . H(15) H 0.1151 0.7907 0.0892 0.0784 Uiso 1.00 calc . . . H(16) H -0.0194 0.7958 0.0313 0.0784 Uiso 1.00 calc . . . H(17) H -0.0268 0.8455 0.1141 0.0784 Uiso 1.00 calc . . . H(18) H 0.1724 0.8490 -0.0636 0.0400 Uiso 1.00 calc . . . H(19) H 0.2907 0.8549 0.0038 0.0400 Uiso 1.00 calc . . . H(20) H 0.2576 0.9427 -0.0489 0.0400 Uiso 1.00 calc . . . H(21) H -0.0736 0.9223 -0.0420 0.0581 Uiso 1.00 calc . . . H(22) H -0.0915 0.9914 0.0295 0.0581 Uiso 1.00 calc . . . H(23) H 0.0148 1.0164 -0.0406 0.0581 Uiso 1.00 calc . . . H(24) H 0.2421 0.9396 0.1227 0.0671 Uiso 1.00 calc . . . H(25) H 0.2089 1.0309 0.0744 0.0671 Uiso 1.00 calc . . . H(26) H 0.0927 0.9925 0.1349 0.0671 Uiso 1.00 calc . . . 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 Cl(1) 0.0212(2) 0.0177(2) 0.0250(2) -0.0043(1) -0.0040(2) 0.0009(1) O(1) 0.0119(5) 0.0156(5) 0.0255(6) -0.0009(4) -0.0001(4) 0.0003(5) O(2) 0.0186(6) 0.0201(6) 0.0177(5) 0.0036(5) -0.0035(5) 0.0011(4) N(1) 0.0245(7) 0.0374(9) 0.0186(6) 0.0041(7) -0.0048(6) 0.0019(6) C(1) 0.0153(6) 0.0145(6) 0.0118(6) 0.0028(6) -0.0018(6) 0.0005(5) C(2) 0.0128(6) 0.0166(7) 0.0143(6) 0.0008(6) -0.0023(5) 0.0023(6) C(3) 0.0178(7) 0.0138(7) 0.0185(7) -0.0007(6) -0.0027(6) -0.0007(6) C(4) 0.0176(7) 0.0141(7) 0.0195(7) 0.0041(6) -0.0009(6) -0.0021(6) C(5) 0.0158(7) 0.0152(7) 0.0185(7) 0.0022(6) 0.0009(6) 0.0004(6) C(6) 0.0160(7) 0.0191(8) 0.0192(7) 0.0043(6) 0.0037(6) -0.0003(6) C(7) 0.0124(7) 0.0261(8) 0.0208(7) 0.0010(6) 0.0026(6) 0.0007(6) C(8) 0.0145(7) 0.0183(7) 0.0248(8) -0.0042(6) 0.0012(6) 0.0027(7) C(9) 0.0154(7) 0.0142(7) 0.0207(7) 0.0009(6) 0.0018(6) 0.0008(6) C(10) 0.0165(7) 0.0129(7) 0.0119(6) 0.0021(5) 0.0011(6) 0.0003(5) C(11) 0.0113(6) 0.0115(6) 0.0160(6) -0.0024(5) 0.0016(6) 0.0008(5) C(12) 0.0125(7) 0.0135(7) 0.0185(7) -0.0028(6) 0.0012(6) 0.0013(6) C(13) 0.0129(6) 0.0148(7) 0.0236(7) 0.0008(6) 0.0013(6) 0.0035(6) C(14) 0.0172(7) 0.0149(6) 0.0249(7) 0.0022(6) 0.0046(6) -0.0022(6) C(15) 0.0155(7) 0.0161(7) 0.0228(8) -0.0008(6) 0.0038(6) -0.0017(6) C(16) 0.0218(7) 0.0260(8) 0.0242(8) -0.0010(7) 0.0078(7) -0.0093(7) C(17) 0.0269(9) 0.0357(10) 0.0174(7) -0.0010(8) 0.0052(7) -0.0041(7) C(18) 0.0191(7) 0.0271(8) 0.0182(7) -0.0020(7) -0.0003(6) 0.0021(7) C(19) 0.0169(7) 0.0170(7) 0.0180(7) 0.0006(6) 0.0009(6) 0.0004(6) C(20) 0.0129(6) 0.0121(6) 0.0166(6) -0.0022(5) 0.0028(6) -0.0005(5) C(21) 0.077(2) 0.056(2) 0.062(2) -0.008(2) 0.020(2) 0.023(1) C(22) 0.054(1) 0.075(2) 0.036(1) 0.008(2) -0.016(1) -0.019(1) C(23) 0.038(1) 0.082(2) 0.0267(10) 0.034(1) -0.0051(9) 0.002(1) C(24) 0.0264(9) 0.039(1) 0.0333(10) 0.0080(9) 0.0004(8) 0.0028(9) #------------------------------------------------------------------------------ _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; 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(2) 1.362(3) . . yes O(2) C(12) 1.360(3) . . yes N(1) C(21) 1.501(5) . . yes N(1) C(22) 1.456(4) . . yes N(1) C(23) 1.474(4) . . yes N(1) C(24) 1.485(4) . . yes C(1) C(2) 1.375(3) . . yes C(1) C(10) 1.423(3) . . yes C(1) C(11) 1.484(3) . . yes C(2) C(3) 1.423(3) . . yes C(3) C(4) 1.373(3) . . yes C(4) C(5) 1.416(3) . . yes C(5) C(6) 1.420(3) . . yes C(5) C(10) 1.431(3) . . yes C(6) C(7) 1.378(4) . . yes C(7) C(8) 1.404(4) . . yes C(8) C(9) 1.381(3) . . yes C(9) C(10) 1.433(3) . . yes C(11) C(12) 1.390(3) . . yes C(11) C(20) 1.427(3) . . yes C(12) C(13) 1.421(3) . . yes C(13) C(14) 1.368(4) . . yes C(14) C(15) 1.428(4) . . yes C(15) C(16) 1.418(4) . . yes C(15) C(20) 1.427(3) . . yes C(16) C(17) 1.363(4) . . yes C(17) C(18) 1.427(4) . . yes C(18) C(19) 1.373(3) . . yes C(19) C(20) 1.425(3) . . 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(21) N(1) C(22) 108.2(3) . . . yes C(21) N(1) C(23) 107.9(3) . . . yes C(21) N(1) C(24) 107.2(3) . . . yes C(22) N(1) C(23) 112.7(3) . . . yes C(22) N(1) C(24) 109.8(3) . . . yes C(23) N(1) C(24) 110.9(2) . . . yes C(2) C(1) C(10) 119.1(2) . . . yes C(2) C(1) C(11) 120.5(2) . . . yes C(10) C(1) C(11) 120.3(2) . . . yes O(1) C(2) C(1) 117.9(2) . . . yes O(1) C(2) C(3) 120.8(2) . . . yes C(1) C(2) C(3) 121.3(2) . . . yes C(2) C(3) C(4) 119.8(2) . . . yes C(3) C(4) C(5) 121.3(2) . . . yes C(4) C(5) C(6) 122.2(2) . . . yes C(4) C(5) C(10) 118.1(2) . . . yes C(6) C(5) C(10) 119.7(2) . . . yes C(5) C(6) C(7) 120.6(2) . . . yes C(6) C(7) C(8) 120.5(2) . . . yes C(7) C(8) C(9) 120.5(2) . . . yes C(8) C(9) C(10) 121.0(2) . . . yes C(1) C(10) C(5) 120.5(2) . . . yes C(1) C(10) C(9) 121.8(2) . . . yes C(5) C(10) C(9) 117.8(2) . . . yes C(1) C(11) C(12) 121.1(2) . . . yes C(1) C(11) C(20) 120.1(2) . . . yes C(12) C(11) C(20) 118.9(2) . . . yes O(2) C(12) C(11) 118.1(2) . . . yes O(2) C(12) C(13) 120.9(2) . . . yes C(11) C(12) C(13) 121.0(2) . . . yes C(12) C(13) C(14) 120.3(2) . . . yes C(13) C(14) C(15) 121.1(2) . . . yes C(14) C(15) C(16) 122.4(2) . . . yes C(14) C(15) C(20) 118.3(2) . . . yes C(16) C(15) C(20) 119.3(2) . . . yes C(15) C(16) C(17) 121.2(2) . . . yes C(16) C(17) C(18) 120.1(2) . . . yes C(17) C(18) C(19) 119.9(2) . . . yes C(18) C(19) C(20) 121.2(2) . . . yes C(11) C(20) C(15) 120.4(2) . . . yes C(11) C(20) C(19) 121.2(2) . . . yes C(15) C(20) C(19) 118.3(2) . . . 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 O(1) C(2) C(1) C(10) 179.5(2) . . . . yes O(1) C(2) C(1) C(11) -3.8(3) . . . . yes O(1) C(2) C(3) C(4) 179.3(2) . . . . yes O(2) C(12) C(11) C(1) 2.5(3) . . . . yes O(2) C(12) C(11) C(20) -178.7(2) . . . . yes O(2) C(12) C(13) C(14) 178.5(2) . . . . yes C(1) C(2) C(3) C(4) -1.1(4) . . . . yes C(1) C(10) C(5) C(4) -2.0(3) . . . . yes C(1) C(10) C(5) C(6) 178.1(2) . . . . yes C(1) C(10) C(9) C(8) -178.9(2) . . . . yes C(1) C(11) C(12) C(13) -177.6(2) . . . . yes C(1) C(11) C(20) C(15) 178.7(2) . . . . yes C(1) C(11) C(20) C(19) 1.7(3) . . . . yes C(2) C(1) C(10) C(5) 1.6(3) . . . . yes C(2) C(1) C(10) C(9) -179.7(2) . . . . yes C(2) C(1) C(11) C(12) 79.3(3) . . . . yes C(2) C(1) C(11) C(20) -99.5(3) . . . . yes C(2) C(3) C(4) C(5) 0.8(4) . . . . yes C(3) C(2) C(1) C(10) 0.0(3) . . . . yes C(3) C(2) C(1) C(11) 176.7(2) . . . . yes C(3) C(4) C(5) C(6) -179.3(2) . . . . yes C(3) C(4) C(5) C(10) 0.8(4) . . . . yes C(4) C(5) C(6) C(7) -178.5(2) . . . . yes C(4) C(5) C(10) C(9) 179.3(2) . . . . yes C(5) C(6) C(7) C(8) -1.4(4) . . . . yes C(5) C(10) C(1) C(11) -175.1(2) . . . . yes C(5) C(10) C(9) C(8) -0.2(4) . . . . yes C(6) C(5) C(10) C(9) -0.6(3) . . . . yes C(6) C(7) C(8) C(9) 0.6(4) . . . . yes C(7) C(6) C(5) C(10) 1.4(4) . . . . yes C(7) C(8) C(9) C(10) 0.2(4) . . . . yes C(9) C(10) C(1) C(11) 3.5(3) . . . . yes C(10) C(1) C(11) C(12) -104.1(3) . . . . yes C(10) C(1) C(11) C(20) 77.2(3) . . . . yes C(11) C(12) C(13) C(14) -1.4(3) . . . . yes C(11) C(20) C(15) C(14) -0.8(3) . . . . yes C(11) C(20) C(15) C(16) -177.8(2) . . . . yes C(11) C(20) C(19) C(18) 176.6(2) . . . . yes C(12) C(11) C(20) C(15) -0.1(3) . . . . yes C(12) C(11) C(20) C(19) -177.1(2) . . . . yes C(12) C(13) C(14) C(15) 0.4(4) . . . . yes C(13) C(12) C(11) C(20) 1.2(3) . . . . yes C(13) C(14) C(15) C(16) 177.5(2) . . . . yes C(13) C(14) C(15) C(20) 0.7(4) . . . . yes C(14) C(15) C(16) C(17) -175.5(2) . . . . yes C(14) C(15) C(20) C(19) 176.3(2) . . . . yes C(15) C(16) C(17) C(18) -0.8(4) . . . . yes C(15) C(20) C(19) C(18) -0.6(4) . . . . yes C(16) C(15) C(20) C(19) -0.7(4) . . . . yes C(16) C(17) C(18) C(19) -0.5(4) . . . . yes C(17) C(16) C(15) C(20) 1.4(4) . . . . yes C(17) C(18) C(19) C(20) 1.1(4) . . . . yes C(17) C(18) C(19) C(20) 1.1(4) . . . . yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Cl(1) O(1) 3.016(2) . . ? Cl(1) O(2) 3.101(2) . 4_655 ? O(1) C(7) 3.294(3) . 1_655 ? O(1) C(23) 3.310(4) . 3_565 ? O(1) C(17) 3.521(3) . 2_565 ? O(1) C(6) 3.599(3) . 1_655 ? O(2) C(18) 3.559(3) . 2_565 ? O(2) C(7) 3.593(3) . 1_655 ? C(2) C(17) 3.577(4) . 2_565 ? C(3) C(21) 3.410(5) . . ? C(3) C(17) 3.561(4) . 2_565 ? C(5) C(22) 3.438(4) . 4_545 ? C(5) C(24) 3.548(4) . 3_465 ? C(6) C(22) 3.392(4) . 4_545 ? C(6) C(24) 3.481(4) . 3_465 ? C(7) C(22) 3.591(4) . 4_545 ? C(15) C(23) 3.391(5) . 3_565 ? C(19) C(23) 3.558(4) . 3_565 ? C(20) C(23) 3.276(4) . 3_565 ? #------------------------------------------------------------------------------ loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_site_distance_DH _geom_hbond_site_distance_HA _geom_hbond_site_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O(1) H(1) Cl(1) . . 1_555 0.908 2.164 3.016(1) 156.094 no #------------------------------------------------------------------------------