# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_General _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef '- compound3af.cif' _audit_creation_date 2012-06-25 _audit_creation_method 'by CrystalStructure 3.8' _audit_update_record ? #============================================================================== # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Ryo Shintani' _publ_contact_author_email shintani@kuchem.kyoto-u.ac.jp _publ_contact_author_fax 'ENTER FAX NUMBER' _publ_contact_author_phone 'ENTER PHONE NUMBER' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_category 'CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; ENTER SECTION TITLE ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Ryo Shintani' ; FIRST AUTHORS FOOTNOTES ; ; FIRST AUTHORS ADDRESS ; 'Tomoaki Ito' '' '' 'Midori Nagamoto' '' '' 'Haruka Otomo' '' '' 'Tamio Hayashi' '' '' _publ_section_synopsis ; ENTER SYNOPSIS ; #============================================================================== # TEXT _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Rigaku Americas and Rigaku Corporation. (2007). CrystalStructure (Version 3.8). Single Crystal Structure Analysis Software. Rigaku Americas, 9009 TX, USA 77381-5209. Rigaku, Tokyo 196-8666, Japan. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M., Polidori, G., and Camalli, M. (1994) J. Appl. Cryst., 27, 435. SIR92 Sheldrick, G.M. (1997). SHELXL97. University of Gottingen, Germany. ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ; #============================================================================== data__20623yuki _database_code_depnum_ccdc_archive 'CCDC 892796' #TrackingRef '- compound3af.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C19 H24 Cl N O3 ' _chemical_formula_moiety 'C19 H24 Cl N O3 ' _chemical_formula_weight 349.86 _chemical_melting_point ? _chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 8.71555(18) _cell_length_b 8.71796(19) _cell_length_c 12.4456(3) _cell_angle_alpha 90.0000 _cell_angle_beta 104.9876(14) _cell_angle_gamma 90.0000 _cell_volume 913.47(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 9073 _cell_measurement_theta_min 3.7 _cell_measurement_theta_max 68.2 _cell_measurement_temperature 93.1 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372.00 _exptl_absorpt_coefficient_mu 1.982 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.564 _exptl_absorpt_correction_T_max 0.673 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93(1) _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 9740 _diffrn_reflns_av_R_equivalents 0.057 _diffrn_reflns_theta_max 68.22 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 68.22 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. 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 3224 _reflns_number_gt 2892 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1020 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 3224 _refine_ls_number_parameters 219 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0535P)^2^+0.0256P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0040 _refine_diff_density_max 0.19 _refine_diff_density_min -0.25 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1446 Friedel Pairs' _refine_ls_abs_structure_Flack 0.040(15) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; Cl Cl 0.364 0.702 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.031 0.018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.049 0.032 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl(1) Cl -1.25860(8) 0.24094(9) -0.15069(6) 0.0483(2) Uani 1.00 1 d . . . O(2) O -0.73991(17) -0.21445(17) -0.21510(12) 0.0244(3) Uani 1.00 1 d . . . O(3) O -1.07046(18) -0.21880(18) -0.14905(13) 0.0253(3) Uani 1.00 1 d . . . O(1) O -0.8167(2) -0.3136(2) -0.38844(15) 0.0383(4) Uani 1.00 1 d . . . N(1) N -0.9832(2) 0.0227(2) -0.17451(16) 0.0225(4) Uani 1.00 1 d . . . C(5) C -0.9969(2) -0.1507(2) -0.32236(18) 0.0213(5) Uani 1.00 1 d . . . C(9) C -1.1369(2) -0.2396(2) -0.39408(18) 0.0216(4) Uani 1.00 1 d . . . C(6) C -1.0221(2) -0.1241(2) -0.20511(18) 0.0212(4) Uani 1.00 1 d . . . C(13) C -1.2880(3) -0.4752(3) -0.4218(2) 0.0335(6) Uani 1.00 1 d . . . C(4) C -0.9718(2) 0.0150(2) -0.35964(19) 0.0255(5) Uani 1.00 1 d . . . C(3) C -0.9143(2) 0.1025(2) -0.25171(19) 0.0235(5) Uani 1.00 1 d . . . C(18) C -0.4906(2) -0.1924(3) -0.2717(2) 0.0317(5) Uani 1.00 1 d . . . C(11) C -1.3777(2) -0.2612(3) -0.54135(19) 0.0309(5) Uani 1.00 1 d . . . C(10) C -1.2466(2) -0.1760(2) -0.48495(19) 0.0250(5) Uani 1.00 1 d . . . C(8) C -1.1540(3) 0.0999(2) -0.0532(2) 0.0310(5) Uani 1.00 1 d . . . C(2) C -0.8957(3) 0.2743(2) -0.2495(2) 0.0334(6) Uani 1.00 1 d . . . C(12) C -1.4001(2) -0.4093(3) -0.5099(2) 0.0336(6) Uani 1.00 1 d . . . C(16) C -0.5721(2) -0.2683(3) -0.19196(19) 0.0271(5) Uani 1.00 1 d . . . C(15) C -0.8417(2) -0.2389(2) -0.31377(19) 0.0240(5) Uani 1.00 1 d . . . C(7) C -0.9864(3) 0.0770(2) -0.0643(2) 0.0277(5) Uani 1.00 1 d . . . C(1) C -0.7511(2) 0.1717(2) -0.2133(2) 0.0306(5) Uani 1.00 1 d . . . C(14) C -1.1594(2) -0.3909(2) -0.3645(2) 0.0277(5) Uani 1.00 1 d . . . C(19) C -0.5026(3) -0.2083(3) -0.0751(2) 0.0381(6) Uani 1.00 1 d . . . C(17) C -0.5667(3) -0.4417(3) -0.1958(2) 0.0433(7) Uani 1.00 1 d . . . H(6) H -0.8915 0.0173 -0.4032 0.031 Uiso 1.00 1 c R . . H(7) H -0.9343 0.1845 -0.0526 0.033 Uiso 1.00 1 c R . . H(8) H -0.9373 0.0035 -0.0126 0.032 Uiso 1.00 1 c R . . H(9) H -1.2180 0.0115 -0.0538 0.039 Uiso 1.00 1 c R . . H(10) H -1.1500 0.1395 0.0252 0.039 Uiso 1.00 1 c R . . H(12) H -1.4503 -0.2126 -0.6077 0.037 Uiso 1.00 1 c R . . H(13) H -1.4914 -0.4702 -0.5493 0.041 Uiso 1.00 1 c R . . H(14) H -1.2986 -0.5864 -0.3986 0.039 Uiso 1.00 1 c R . . H(15) H -1.0847 -0.4449 -0.3047 0.033 Uiso 1.00 1 c R . . H(19) H -0.5474 -0.2180 -0.3483 0.038 Uiso 1.00 1 c R . . H(16) H -0.6423 -0.4843 -0.1577 0.052 Uiso 1.00 1 c R . . H(17) H -0.4593 -0.4770 -0.1588 0.052 Uiso 1.00 1 c R . . H(18) H -0.5950 -0.4759 -0.2735 0.052 Uiso 1.00 1 c R . . H(1) H -0.6797 0.1633 -0.2634 0.037 Uiso 1.00 1 c R . . H(2) H -0.6971 0.1668 -0.1330 0.037 Uiso 1.00 1 c R . . H(3) H -0.9299 0.3319 -0.1911 0.040 Uiso 1.00 1 c R . . H(4) H -0.9125 0.3283 -0.3216 0.040 Uiso 1.00 1 c R . . H(22) H -0.3866 -0.2047 -0.0598 0.046 Uiso 1.00 1 c R . . H(23) H -0.5329 -0.2764 -0.0214 0.046 Uiso 1.00 1 c R . . H(24) H -0.5434 -0.1049 -0.0686 0.046 Uiso 1.00 1 c R . . H(5) H -1.0725 0.0586 -0.4053 0.031 Uiso 1.00 1 c R . . H(11) H -1.2319 -0.0745 -0.5083 0.030 Uiso 1.00 1 c R . . H(20) H -0.3808 -0.2291 -0.2567 0.038 Uiso 1.00 1 c R . . H(21) H -0.4908 -0.0809 -0.2617 0.038 Uiso 1.00 1 c R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl(1) 0.0432(3) 0.0528(4) 0.0500(4) 0.0188(3) 0.0140(3) -0.0002(3) O(2) 0.0205(8) 0.0276(8) 0.0251(8) 0.0020(6) 0.0058(6) -0.0018(6) O(3) 0.0295(8) 0.0232(8) 0.0248(8) -0.0018(6) 0.0098(6) 0.0024(6) O(1) 0.0298(9) 0.0494(11) 0.0344(10) 0.0071(8) 0.0058(7) -0.0184(9) N(1) 0.0256(9) 0.0198(9) 0.0238(10) 0.0004(7) 0.0095(7) -0.0028(7) C(5) 0.0244(11) 0.0186(11) 0.0214(11) -0.0006(9) 0.0069(9) -0.0006(8) C(9) 0.0228(10) 0.0219(12) 0.0227(11) 0.0003(9) 0.0108(8) -0.0061(9) C(6) 0.0172(10) 0.0229(11) 0.0230(11) 0.0021(9) 0.0041(9) -0.0000(9) C(13) 0.0364(14) 0.0297(13) 0.0389(15) -0.0064(11) 0.0177(11) -0.0086(12) C(4) 0.0303(12) 0.0214(11) 0.0250(12) -0.0011(9) 0.0079(9) 0.0002(10) C(3) 0.0249(12) 0.0207(12) 0.0261(12) -0.0008(9) 0.0089(9) 0.0003(10) C(18) 0.0271(12) 0.0385(14) 0.0309(13) 0.0035(10) 0.0101(10) 0.0028(11) C(11) 0.0258(11) 0.0442(14) 0.0240(12) 0.0055(12) 0.0086(9) -0.0060(12) C(10) 0.0265(12) 0.0254(13) 0.0244(12) 0.0050(9) 0.0090(9) -0.0023(9) C(8) 0.0342(13) 0.0315(14) 0.0304(13) -0.0003(11) 0.0136(10) -0.0048(11) C(2) 0.0453(14) 0.0197(13) 0.0409(14) -0.0032(10) 0.0218(12) -0.0032(11) C(12) 0.0273(13) 0.0408(15) 0.0357(14) -0.0104(11) 0.0136(11) -0.0162(12) C(16) 0.0207(11) 0.0294(12) 0.0315(12) 0.0073(10) 0.0071(9) 0.0035(10) C(15) 0.0252(11) 0.0218(12) 0.0260(11) -0.0012(9) 0.0081(9) -0.0027(10) C(7) 0.0327(13) 0.0277(12) 0.0239(12) 0.0017(10) 0.0095(10) -0.0046(10) C(1) 0.0332(13) 0.0271(12) 0.0327(13) -0.0098(10) 0.0103(11) -0.0069(10) C(14) 0.0320(12) 0.0233(12) 0.0298(13) 0.0030(9) 0.0115(10) -0.0005(10) C(19) 0.0253(12) 0.0587(17) 0.0293(13) 0.0006(11) 0.0052(10) 0.0063(13) C(17) 0.0331(14) 0.0293(15) 0.066(2) 0.0078(11) 0.0109(14) 0.0100(13) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Cl(1) C(8) 1.801(2) yes . . O(2) C(16) 1.491(2) yes . . O(2) C(15) 1.333(2) yes . . O(3) C(6) 1.224(2) yes . . O(1) C(15) 1.200(3) yes . . N(1) C(6) 1.353(2) yes . . N(1) C(3) 1.438(3) yes . . N(1) C(7) 1.458(3) yes . . C(5) C(9) 1.525(2) yes . . C(5) C(6) 1.548(3) yes . . C(5) C(4) 1.550(3) yes . . C(5) C(15) 1.535(3) yes . . C(9) C(10) 1.394(2) yes . . C(9) C(14) 1.397(3) yes . . C(13) C(12) 1.390(3) yes . . C(13) C(14) 1.375(3) yes . . C(4) C(3) 1.513(3) yes . . C(3) C(2) 1.506(3) yes . . C(3) C(1) 1.505(3) yes . . C(18) C(16) 1.515(3) yes . . C(11) C(10) 1.391(3) yes . . C(11) C(12) 1.378(4) yes . . C(8) C(7) 1.515(3) yes . . C(2) C(1) 1.516(3) yes . . C(16) C(19) 1.517(3) yes . . C(16) C(17) 1.514(3) yes . . C(13) H(14) 1.023 no . . C(4) H(6) 0.990 no . . C(4) H(5) 0.990 no . . C(18) H(19) 0.980 no . . C(18) H(20) 0.980 no . . C(18) H(21) 0.980 no . . C(11) H(12) 0.995 no . . C(10) H(11) 0.950 no . . C(8) H(9) 0.950 no . . C(8) H(10) 1.028 no . . C(2) H(3) 0.990 no . . C(2) H(4) 0.990 no . . C(12) H(13) 0.976 no . . C(7) H(7) 1.035 no . . C(7) H(8) 0.931 no . . C(1) H(1) 0.990 no . . C(1) H(2) 0.990 no . . C(14) H(15) 0.974 no . . C(19) H(22) 0.980 no . . C(19) H(23) 0.980 no . . C(19) H(24) 0.980 no . . C(17) H(16) 0.980 no . . C(17) H(17) 0.980 no . . C(17) H(18) 0.980 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(16) O(2) C(15) 120.88(18) yes . . . C(6) N(1) C(3) 112.78(19) yes . . . C(6) N(1) C(7) 120.5(2) yes . . . C(3) N(1) C(7) 125.75(18) yes . . . C(9) C(5) C(6) 109.91(18) yes . . . C(9) C(5) C(4) 116.89(16) yes . . . C(9) C(5) C(15) 110.09(17) yes . . . C(6) C(5) C(4) 102.02(17) yes . . . C(6) C(5) C(15) 110.27(16) yes . . . C(4) C(5) C(15) 107.32(19) yes . . . C(5) C(9) C(10) 123.37(19) yes . . . C(5) C(9) C(14) 118.14(17) yes . . . C(10) C(9) C(14) 118.45(19) yes . . . O(3) C(6) N(1) 125.1(2) yes . . . O(3) C(6) C(5) 126.18(19) yes . . . N(1) C(6) C(5) 108.69(19) yes . . . C(12) C(13) C(14) 120.1(2) yes . . . C(5) C(4) C(3) 104.13(18) yes . . . N(1) C(3) C(4) 104.45(18) yes . . . N(1) C(3) C(2) 122.1(2) yes . . . N(1) C(3) C(1) 120.40(18) yes . . . C(4) C(3) C(2) 121.8(2) yes . . . C(4) C(3) C(1) 123.6(2) yes . . . C(2) C(3) C(1) 60.46(15) yes . . . C(10) C(11) C(12) 121.0(2) yes . . . C(9) C(10) C(11) 119.9(2) yes . . . Cl(1) C(8) C(7) 111.14(18) yes . . . C(3) C(2) C(1) 59.74(15) yes . . . C(13) C(12) C(11) 119.3(2) yes . . . O(2) C(16) C(18) 109.81(18) yes . . . O(2) C(16) C(19) 101.84(19) yes . . . O(2) C(16) C(17) 110.19(18) yes . . . C(18) C(16) C(19) 109.8(2) yes . . . C(18) C(16) C(17) 113.1(2) yes . . . C(19) C(16) C(17) 111.5(2) yes . . . O(2) C(15) O(1) 126.1(2) yes . . . O(2) C(15) C(5) 110.39(19) yes . . . O(1) C(15) C(5) 123.42(18) yes . . . N(1) C(7) C(8) 112.45(18) yes . . . C(3) C(1) C(2) 59.80(15) yes . . . C(9) C(14) C(13) 121.3(2) yes . . . C(12) C(13) H(14) 121.1 no . . . C(14) C(13) H(14) 118.8 no . . . C(5) C(4) H(6) 110.9 no . . . C(5) C(4) H(5) 110.9 no . . . C(3) C(4) H(6) 110.9 no . . . C(3) C(4) H(5) 110.9 no . . . H(6) C(4) H(5) 108.9 no . . . C(16) C(18) H(19) 109.5 no . . . C(16) C(18) H(20) 109.5 no . . . C(16) C(18) H(21) 109.5 no . . . H(19) C(18) H(20) 109.5 no . . . H(19) C(18) H(21) 109.5 no . . . H(20) C(18) H(21) 109.5 no . . . C(10) C(11) H(12) 117.0 no . . . C(12) C(11) H(12) 121.9 no . . . C(9) C(10) H(11) 120.1 no . . . C(11) C(10) H(11) 120.1 no . . . Cl(1) C(8) H(9) 110.8 no . . . Cl(1) C(8) H(10) 107.3 no . . . C(7) C(8) H(9) 118.1 no . . . C(7) C(8) H(10) 109.5 no . . . H(9) C(8) H(10) 98.9 no . . . C(3) C(2) H(3) 117.8 no . . . C(3) C(2) H(4) 117.8 no . . . C(1) C(2) H(3) 117.8 no . . . C(1) C(2) H(4) 117.8 no . . . H(3) C(2) H(4) 114.9 no . . . C(13) C(12) H(13) 119.1 no . . . C(11) C(12) H(13) 121.6 no . . . N(1) C(7) H(7) 108.2 no . . . N(1) C(7) H(8) 108.1 no . . . C(8) C(7) H(7) 105.4 no . . . C(8) C(7) H(8) 108.0 no . . . H(7) C(7) H(8) 114.7 no . . . C(3) C(1) H(1) 117.8 no . . . C(3) C(1) H(2) 117.8 no . . . C(2) C(1) H(1) 117.8 no . . . C(2) C(1) H(2) 117.8 no . . . H(1) C(1) H(2) 114.9 no . . . C(9) C(14) H(15) 123.1 no . . . C(13) C(14) H(15) 115.6 no . . . C(16) C(19) H(22) 109.5 no . . . C(16) C(19) H(23) 109.5 no . . . C(16) C(19) H(24) 109.5 no . . . H(22) C(19) H(23) 109.5 no . . . H(22) C(19) H(24) 109.5 no . . . H(23) C(19) H(24) 109.5 no . . . C(16) C(17) H(16) 109.5 no . . . C(16) C(17) H(17) 109.5 no . . . C(16) C(17) H(18) 109.5 no . . . H(16) C(17) H(17) 109.5 no . . . H(16) C(17) H(18) 109.5 no . . . H(17) C(17) H(18) 109.5 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(16) O(2) C(15) O(1) 6.3(3) ? . . . . C(16) O(2) C(15) C(5) -170.95(18) ? . . . . C(15) O(2) C(16) C(18) 60.7(2) ? . . . . C(15) O(2) C(16) C(19) 177.1(2) ? . . . . C(15) O(2) C(16) C(17) -64.5(2) ? . . . . C(6) N(1) C(3) C(4) 22.5(2) ? . . . . C(6) N(1) C(3) C(2) 166.03(19) ? . . . . C(6) N(1) C(3) C(1) -121.8(2) ? . . . . C(3) N(1) C(6) O(3) 173.87(19) ? . . . . C(3) N(1) C(6) C(5) -6.8(2) ? . . . . C(6) N(1) C(7) C(8) -73.9(2) ? . . . . C(7) N(1) C(6) O(3) 4.4(3) ? . . . . C(7) N(1) C(6) C(5) -176.23(18) ? . . . . C(3) N(1) C(7) C(8) 118.1(2) ? . . . . C(7) N(1) C(3) C(4) -168.7(2) ? . . . . C(7) N(1) C(3) C(2) -25.2(3) ? . . . . C(7) N(1) C(3) C(1) 46.9(3) ? . . . . C(9) C(5) C(6) O(3) 43.3(2) ? . . . . C(9) C(5) C(6) N(1) -136.01(17) ? . . . . C(6) C(5) C(9) C(10) 111.1(2) ? . . . . C(6) C(5) C(9) C(14) -66.4(2) ? . . . . C(9) C(5) C(4) C(3) 143.7(2) ? . . . . C(4) C(5) C(9) C(10) -4.5(3) ? . . . . C(4) C(5) C(9) C(14) 178.0(2) ? . . . . C(9) C(5) C(15) O(2) -147.47(19) ? . . . . C(9) C(5) C(15) O(1) 35.2(3) ? . . . . C(15) C(5) C(9) C(10) -127.2(2) ? . . . . C(15) C(5) C(9) C(14) 55.2(2) ? . . . . C(6) C(5) C(4) C(3) 23.8(2) ? . . . . C(4) C(5) C(6) O(3) 168.01(19) ? . . . . C(4) C(5) C(6) N(1) -11.3(2) ? . . . . C(6) C(5) C(15) O(2) -26.0(2) ? . . . . C(6) C(5) C(15) O(1) 156.6(2) ? . . . . C(15) C(5) C(6) O(3) -78.2(2) ? . . . . C(15) C(5) C(6) N(1) 102.4(2) ? . . . . C(4) C(5) C(15) O(2) 84.3(2) ? . . . . C(4) C(5) C(15) O(1) -93.0(2) ? . . . . C(15) C(5) C(4) C(3) -92.1(2) ? . . . . C(5) C(9) C(10) C(11) -175.3(2) ? . . . . C(5) C(9) C(14) C(13) 176.4(2) ? . . . . C(10) C(9) C(14) C(13) -1.3(4) ? . . . . C(14) C(9) C(10) C(11) 2.2(3) ? . . . . C(12) C(13) C(14) C(9) -1.0(4) ? . . . . C(14) C(13) C(12) C(11) 2.2(4) ? . . . . C(5) C(4) C(3) N(1) -28.2(2) ? . . . . C(5) C(4) C(3) C(2) -171.8(2) ? . . . . C(5) C(4) C(3) C(1) 114.8(2) ? . . . . N(1) C(3) C(2) C(1) 109.4(2) ? . . . . N(1) C(3) C(1) C(2) -112.0(2) ? . . . . C(4) C(3) C(2) C(1) -113.3(2) ? . . . . C(4) C(3) C(1) C(2) 110.6(2) ? . . . . C(10) C(11) C(12) C(13) -1.2(4) ? . . . . C(12) C(11) C(10) C(9) -1.0(4) ? . . . . Cl(1) C(8) C(7) N(1) -60.9(2) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O(3) C(18) 3.591(2) ? . 1_455 O(3) C(8) 3.181(2) ? . 2_345 O(3) C(7) 3.128(2) ? . 2_345 O(1) C(4) 3.532(2) ? . 2_344 C(4) O(1) 3.532(2) ? . 2_354 C(18) O(3) 3.591(2) ? . 1_655 C(11) C(1) 3.563(3) ? . 2_344 C(8) O(3) 3.181(2) ? . 2_355 C(7) O(3) 3.128(2) ? . 2_355 C(1) C(11) 3.563(3) ? . 2_354 Cl(1) H(8) 3.239 ? . 2_355 Cl(1) H(12) 3.420 ? . 2_254 Cl(1) H(14) 3.369 ? . 1_565 Cl(1) H(17) 3.004 ? . 1_465 Cl(1) H(23) 3.151 ? . 2_355 Cl(1) H(21) 3.525 ? . 1_455 O(2) H(10) 3.050 ? . 2_345 O(3) H(7) 2.637 ? . 2_345 O(3) H(8) 3.137 ? . 2_345 O(3) H(10) 2.462 ? . 2_345 O(3) H(22) 3.228 ? . 1_455 O(3) H(20) 2.691 ? . 1_455 O(1) H(6) 3.458 ? . 2_344 O(1) H(4) 3.391 ? . 1_545 O(1) H(5) 2.735 ? . 2_344 O(1) H(11) 2.699 ? . 2_344 C(9) H(6) 3.353 ? . 2_344 C(9) H(20) 3.054 ? . 1_455 C(6) H(10) 3.126 ? . 2_345 C(6) H(20) 3.160 ? . 1_455 C(13) H(6) 2.993 ? . 2_344 C(13) H(12) 3.171 ? . 2_244 C(13) H(19) 3.470 ? . 1_455 C(13) H(19) 3.550 ? . 2_344 C(13) H(20) 3.215 ? . 1_455 C(18) H(9) 3.582 ? . 1_655 C(18) H(13) 2.925 ? . 2_354 C(11) H(6) 3.248 ? . 2_344 C(11) H(13) 3.111 ? . 2_254 C(11) H(14) 3.122 ? . 2_254 C(11) H(19) 3.152 ? . 1_455 C(11) H(18) 3.357 ? . 2_354 C(11) H(1) 2.687 ? . 2_344 C(11) H(4) 3.486 ? . 2_344 C(11) H(20) 3.560 ? . 1_455 C(10) H(6) 3.377 ? . 2_344 C(10) H(13) 3.020 ? . 2_254 C(10) H(19) 3.493 ? . 1_455 C(10) H(18) 3.441 ? . 2_354 C(10) H(1) 3.339 ? . 2_344 C(10) H(4) 3.074 ? . 2_344 C(10) H(20) 3.371 ? . 1_455 C(8) H(22) 3.329 ? . 1_455 C(8) H(23) 3.284 ? . 2_355 C(2) H(15) 2.931 ? . 1_565 C(2) H(16) 3.050 ? . 1_565 C(2) H(18) 3.479 ? . 1_565 C(12) H(6) 3.075 ? . 2_344 C(12) H(12) 3.438 ? . 2_244 C(12) H(19) 3.132 ? . 1_455 C(12) H(19) 3.185 ? . 2_344 C(12) H(1) 3.140 ? . 2_344 C(12) H(11) 3.576 ? . 2_244 C(12) H(20) 3.486 ? . 1_455 C(12) H(21) 3.134 ? . 2_344 C(1) H(12) 3.328 ? . 2_354 C(1) H(16) 3.167 ? . 1_565 C(1) H(18) 3.518 ? . 1_565 C(1) H(22) 3.471 ? . 2_455 C(1) H(23) 3.336 ? . 2_455 C(14) H(6) 3.140 ? . 2_344 C(14) H(3) 3.502 ? . 1_545 C(14) H(4) 3.211 ? . 1_545 C(14) H(20) 2.975 ? . 1_455 C(19) H(9) 3.092 ? . 1_655 C(19) H(10) 3.505 ? . 2_345 C(19) H(16) 3.451 ? . 2_455 C(19) H(2) 2.931 ? . 2_445 C(17) H(12) 3.431 ? . 2_344 C(17) H(24) 3.484 ? . 2_445 H(6) O(1) 3.458 ? . 2_354 H(6) C(9) 3.353 ? . 2_354 H(6) C(13) 2.993 ? . 2_354 H(6) C(11) 3.248 ? . 2_354 H(6) C(10) 3.377 ? . 2_354 H(6) C(12) 3.075 ? . 2_354 H(6) C(14) 3.140 ? . 2_354 H(6) H(13) 3.538 ? . 2_354 H(6) H(14) 3.429 ? . 2_354 H(7) O(3) 2.637 ? . 2_355 H(7) H(8) 3.180 ? . 2_355 H(7) H(9) 3.276 ? . 2_355 H(7) H(22) 2.947 ? . 2_455 H(8) Cl(1) 3.239 ? . 2_345 H(8) O(3) 3.137 ? . 2_355 H(8) H(7) 3.180 ? . 2_345 H(8) H(10) 3.276 ? . 2_345 H(8) H(17) 3.565 ? . 2_455 H(8) H(3) 3.395 ? . 2_345 H(9) C(18) 3.582 ? . 1_455 H(9) C(19) 3.092 ? . 1_455 H(9) H(7) 3.276 ? . 2_345 H(9) H(16) 3.173 ? . 2_355 H(9) H(3) 3.372 ? . 2_345 H(9) H(22) 2.380 ? . 1_455 H(9) H(23) 3.172 ? . 2_355 H(9) H(24) 2.973 ? . 1_455 H(9) H(20) 3.308 ? . 1_455 H(9) H(21) 3.133 ? . 1_455 H(10) O(2) 3.050 ? . 2_355 H(10) O(3) 2.462 ? . 2_355 H(10) C(6) 3.126 ? . 2_355 H(10) C(19) 3.505 ? . 2_355 H(10) H(8) 3.276 ? . 2_355 H(10) H(16) 2.950 ? . 2_355 H(10) H(3) 3.346 ? . 2_345 H(10) H(23) 2.848 ? . 2_355 H(12) Cl(1) 3.420 ? . 2_244 H(12) C(13) 3.171 ? . 2_254 H(12) C(12) 3.438 ? . 2_254 H(12) C(1) 3.328 ? . 2_344 H(12) C(17) 3.431 ? . 2_354 H(12) H(13) 3.009 ? . 2_254 H(12) H(14) 2.469 ? . 2_254 H(12) H(19) 3.542 ? . 1_455 H(12) H(17) 3.478 ? . 2_354 H(12) H(18) 2.628 ? . 2_354 H(12) H(1) 2.443 ? . 2_344 H(12) H(4) 3.513 ? . 2_344 H(12) H(21) 3.575 ? . 2_344 H(13) C(18) 2.925 ? . 2_344 H(13) C(11) 3.111 ? . 2_244 H(13) C(10) 3.020 ? . 2_244 H(13) H(6) 3.538 ? . 2_344 H(13) H(12) 3.009 ? . 2_244 H(13) H(19) 3.458 ? . 1_455 H(13) H(19) 2.575 ? . 2_344 H(13) H(1) 3.288 ? . 2_344 H(13) H(11) 2.838 ? . 2_244 H(13) H(20) 3.282 ? . 2_344 H(13) H(21) 2.510 ? . 2_344 H(14) Cl(1) 3.369 ? . 1_545 H(14) C(11) 3.122 ? . 2_244 H(14) H(6) 3.429 ? . 2_344 H(14) H(12) 2.469 ? . 2_244 H(14) H(19) 3.294 ? . 2_344 H(14) H(18) 3.479 ? . 1_455 H(14) H(4) 3.336 ? . 1_545 H(15) C(2) 2.931 ? . 1_545 H(15) H(3) 2.573 ? . 1_545 H(15) H(4) 2.523 ? . 1_545 H(15) H(20) 3.370 ? . 1_455 H(19) C(13) 3.470 ? . 1_655 H(19) C(13) 3.550 ? . 2_354 H(19) C(11) 3.152 ? . 1_655 H(19) C(10) 3.493 ? . 1_655 H(19) C(12) 3.132 ? . 1_655 H(19) C(12) 3.185 ? . 2_354 H(19) H(12) 3.542 ? . 1_655 H(19) H(13) 3.458 ? . 1_655 H(19) H(13) 2.575 ? . 2_354 H(19) H(14) 3.294 ? . 2_354 H(16) C(2) 3.050 ? . 1_545 H(16) C(1) 3.167 ? . 1_545 H(16) C(19) 3.451 ? . 2_445 H(16) H(9) 3.173 ? . 2_345 H(16) H(10) 2.950 ? . 2_345 H(16) H(1) 3.325 ? . 1_545 H(16) H(2) 3.106 ? . 1_545 H(16) H(3) 2.912 ? . 1_545 H(16) H(4) 3.145 ? . 1_545 H(16) H(22) 3.275 ? . 2_445 H(16) H(23) 3.468 ? . 2_445 H(16) H(24) 3.049 ? . 2_445 H(17) Cl(1) 3.004 ? . 1_645 H(17) H(8) 3.565 ? . 2_445 H(17) H(12) 3.478 ? . 2_344 H(17) H(23) 3.454 ? . 2_445 H(17) H(24) 3.036 ? . 2_445 H(18) C(11) 3.357 ? . 2_344 H(18) C(10) 3.441 ? . 2_344 H(18) C(2) 3.479 ? . 1_545 H(18) C(1) 3.518 ? . 1_545 H(18) H(12) 2.628 ? . 2_344 H(18) H(14) 3.479 ? . 1_655 H(18) H(1) 3.241 ? . 1_545 H(18) H(4) 3.174 ? . 1_545 H(18) H(11) 2.876 ? . 2_344 H(1) C(11) 2.687 ? . 2_354 H(1) C(10) 3.339 ? . 2_354 H(1) C(12) 3.140 ? . 2_354 H(1) H(12) 2.443 ? . 2_354 H(1) H(13) 3.288 ? . 2_354 H(1) H(16) 3.325 ? . 1_565 H(1) H(18) 3.241 ? . 1_565 H(1) H(23) 3.589 ? . 2_455 H(1) H(11) 3.572 ? . 2_354 H(2) C(19) 2.931 ? . 2_455 H(2) H(16) 3.106 ? . 1_565 H(2) H(22) 2.576 ? . 2_455 H(2) H(23) 2.442 ? . 2_455 H(2) H(24) 3.454 ? . 2_455 H(3) C(14) 3.502 ? . 1_565 H(3) H(8) 3.395 ? . 2_355 H(3) H(9) 3.372 ? . 2_355 H(3) H(10) 3.346 ? . 2_355 H(3) H(15) 2.573 ? . 1_565 H(3) H(16) 2.912 ? . 1_565 H(4) O(1) 3.391 ? . 1_565 H(4) C(11) 3.486 ? . 2_354 H(4) C(10) 3.074 ? . 2_354 H(4) C(14) 3.211 ? . 1_565 H(4) H(12) 3.513 ? . 2_354 H(4) H(14) 3.336 ? . 1_565 H(4) H(15) 2.523 ? . 1_565 H(4) H(16) 3.145 ? . 1_565 H(4) H(18) 3.174 ? . 1_565 H(4) H(11) 2.857 ? . 2_354 H(22) O(3) 3.228 ? . 1_655 H(22) C(8) 3.329 ? . 1_655 H(22) C(1) 3.471 ? . 2_445 H(22) H(7) 2.947 ? . 2_445 H(22) H(9) 2.380 ? . 1_655 H(22) H(16) 3.275 ? . 2_455 H(22) H(2) 2.576 ? . 2_445 H(23) Cl(1) 3.151 ? . 2_345 H(23) C(8) 3.284 ? . 2_345 H(23) C(1) 3.336 ? . 2_445 H(23) H(9) 3.172 ? . 2_345 H(23) H(10) 2.848 ? . 2_345 H(23) H(16) 3.468 ? . 2_455 H(23) H(17) 3.454 ? . 2_455 H(23) H(1) 3.589 ? . 2_445 H(23) H(2) 2.442 ? . 2_445 H(23) H(24) 3.084 ? . 2_445 H(24) C(17) 3.484 ? . 2_455 H(24) H(9) 2.973 ? . 1_655 H(24) H(16) 3.049 ? . 2_455 H(24) H(17) 3.036 ? . 2_455 H(24) H(2) 3.454 ? . 2_445 H(24) H(23) 3.084 ? . 2_455 H(5) O(1) 2.735 ? . 2_354 H(11) O(1) 2.699 ? . 2_354 H(11) C(12) 3.576 ? . 2_254 H(11) H(13) 2.838 ? . 2_254 H(11) H(18) 2.876 ? . 2_354 H(11) H(1) 3.572 ? . 2_344 H(11) H(4) 2.857 ? . 2_344 H(20) O(3) 2.691 ? . 1_655 H(20) C(9) 3.054 ? . 1_655 H(20) C(6) 3.160 ? . 1_655 H(20) C(13) 3.215 ? . 1_655 H(20) C(11) 3.560 ? . 1_655 H(20) C(10) 3.371 ? . 1_655 H(20) C(12) 3.486 ? . 1_655 H(20) C(14) 2.975 ? . 1_655 H(20) H(9) 3.308 ? . 1_655 H(20) H(13) 3.282 ? . 2_354 H(20) H(15) 3.370 ? . 1_655 H(21) Cl(1) 3.525 ? . 1_655 H(21) C(12) 3.134 ? . 2_354 H(21) H(9) 3.133 ? . 1_655 H(21) H(12) 3.575 ? . 2_354 H(21) H(13) 2.510 ? . 2_354 #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================