#------------------------------------------------------------------------------ #$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/52/2015279.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2015279 _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _[local]_cod_cif_authors_sg_H-M 'P 21/n' loop_ _publ_author_name 'Linden, Anthony' 'G\"und\"uz, Miyase G.' '\,Sim\,sek, Rahime' '\,Safak, Cihat' _publ_section_title ; Cocrystals of diastereoisomers of 1,4-dihydropyridine derivatives ; _journal_coeditor_code SK3008 _journal_issue 4 _journal_name_full 'Acta Crystallographica, Section C' _journal_page_first o227 _journal_page_last o230 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C19 H19 Cl2 N O3' _chemical_formula_moiety 'C19 H19 Cl2 N O3' _chemical_formula_sum 'C19 H19 Cl2 N O3' _chemical_formula_weight 380.27 _chemical_melting_point 523 _chemical_name_systematic ; (RR,SS)/(RS,SR)-methyl 4-(2,4-chlorophenyl)-2,7-dimethyl- 5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate ; _symmetry_cell_setting monoclinic _atom_sites_solution_hydrogens 'geom and difmap' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 105.4328(19) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.6670(3) _cell_length_b 13.7746(4) _cell_length_c 11.8897(4) _cell_measurement_reflns_used 13345 _cell_measurement_temperature 160.0(10) _cell_measurement_theta_max 25.0 _cell_measurement_theta_min 2.0 _cell_volume 1841.88(10) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 160.0(10) _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '\w scans with \k offsets' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_radiation_source 'Nonius FR590 sealed tube generator' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0721 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 23780 _diffrn_reflns_theta_full 25.04 _diffrn_reflns_theta_max 25.04 _diffrn_reflns_theta_min 2.17 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.369 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_correction_T_min 0.871 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Blessing, 1995)' _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_description tablet _exptl_crystal_F_000 792 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.712 _refine_diff_density_min -0.301 _refine_ls_extinction_coef 0.011(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 254 _refine_ls_number_reflns 3252 _refine_ls_number_restraints 31 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all 0.0706 _refine_ls_R_factor_gt 0.0487 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.073P)^2^+1.1256P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1229 _refine_ls_wR_factor_ref 0.1391 _reflns_number_gt 2469 _reflns_number_total 3252 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk3008.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; Cl Cl 0.1484 0.1585 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992). Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl Cl1 0.22102(6) 0.11917(5) 0.91939(6) 0.0436(3) Uani d . 1 . . Cl Cl2 -0.04745(8) 0.38039(6) 1.06080(7) 0.0573(3) Uani d . 1 . . O O5 0.25975(16) 0.26195(16) 0.71309(16) 0.0457(5) Uani d . 1 . . O O10 -0.17030(19) -0.04887(16) 0.64133(19) 0.0551(6) Uani d . 1 . . O O11 -0.00920(17) -0.00143(14) 0.77785(17) 0.0432(5) Uani d . 1 . . N N1 -0.0879(2) 0.17511(17) 0.4283(2) 0.0374(6) Uani d . 1 . . H H1 -0.132(3) 0.191(2) 0.359(3) 0.049(9) Uiso d . 1 . . C C2 -0.1208(2) 0.10291(19) 0.4935(2) 0.0334(6) Uani d . 1 . . C C3 -0.0553(2) 0.08602(19) 0.6046(2) 0.0318(6) Uani d . 1 . . C C4 0.0522(2) 0.14857(18) 0.6638(2) 0.0302(6) Uani d . 1 . . H H4 0.1215 0.1044 0.6946 0.036 Uiso calc R 1 . . C C4A 0.0836(2) 0.21715(18) 0.5769(2) 0.0302(6) Uani d . 1 . . C C5 0.1923(2) 0.2724(2) 0.6137(2) 0.0367(6) Uani d . 1 A . C C6 0.2229(3) 0.3432(2) 0.5298(3) 0.0514(8) Uani d D 1 . . H H61 0.2768 0.3107 0.4898 0.062 Uiso calc PR 0.488(6) A 1 H H62 0.2669 0.3983 0.5748 0.062 Uiso calc PR 0.488(6) A 1 H H63 0.3105 0.3483 0.5468 0.062 Uiso calc PR 0.512(6) A 2 H H64 0.1918 0.4080 0.5421 0.062 Uiso calc PR 0.512(6) A 2 C C7A 0.1152(4) 0.3832(4) 0.4370(4) 0.0505(19) Uani d PDU 0.488(6) A 1 H H71 0.0671 0.4219 0.4791 0.061 Uiso calc PR 0.488(6) A 1 C C19A 0.1413(10) 0.4487(7) 0.3452(7) 0.086(3) Uani d PDU 0.488(6) A 1 H H191 0.1792 0.4109 0.2951 0.129 Uiso calc PR 0.488(6) A 1 H H192 0.1948 0.5009 0.3830 0.129 Uiso calc PR 0.488(6) A 1 H H193 0.0669 0.4767 0.2977 0.129 Uiso calc PR 0.488(6) A 1 C C7B 0.1730(4) 0.3142(4) 0.4037(4) 0.0461(16) Uani d PDU 0.512(6) A 2 H H72 0.2100 0.2512 0.3905 0.055 Uiso calc PR 0.512(6) A 2 C C19B 0.2082(7) 0.3908(6) 0.3286(6) 0.061(2) Uani d PDU 0.512(6) A 2 H H194 0.1875 0.4551 0.3525 0.092 Uiso calc PR 0.512(6) A 2 H H195 0.1660 0.3795 0.2467 0.092 Uiso calc PR 0.512(6) A 2 H H196 0.2942 0.3875 0.3379 0.092 Uiso calc PR 0.512(6) A 2 C C8 0.0394(2) 0.2989(2) 0.3806(2) 0.0402(7) Uani d D 1 . . H H81 -0.0365 0.3240 0.3303 0.048 Uiso calc PR 0.488(6) A 1 H H82 0.0806 0.2637 0.3302 0.048 Uiso calc PR 0.488(6) A 1 H H83 0.0003 0.3619 0.3860 0.048 Uiso calc PR 0.512(6) A 2 H H84 0.0069 0.2732 0.3007 0.048 Uiso calc PR 0.512(6) A 2 C C8A 0.0131(2) 0.22939(19) 0.4671(2) 0.0322(6) Uani d . 1 A . C C9 -0.2300(2) 0.0493(2) 0.4284(3) 0.0453(7) Uani d . 1 . . H H91 -0.2121 -0.0202 0.4275 0.068 Uiso calc R 1 . . H H92 -0.2557 0.0736 0.3481 0.068 Uiso calc R 1 . . H H93 -0.2935 0.0594 0.4670 0.068 Uiso calc R 1 . . C C10 -0.0871(2) 0.00612(19) 0.6710(2) 0.0356(6) Uani d . 1 . . C C12 -0.0352(3) -0.0761(2) 0.8522(3) 0.0499(8) Uani d . 1 . . H H121 -0.1179 -0.0698 0.8557 0.075 Uiso calc R 1 . . H H122 0.0182 -0.0694 0.9308 0.075 Uiso calc R 1 . . H H123 -0.0237 -0.1400 0.8206 0.075 Uiso calc R 1 . . C C13 0.0305(2) 0.20598(18) 0.7668(2) 0.0306(6) Uani d . 1 . . C C14 0.1005(2) 0.19828(18) 0.8809(2) 0.0326(6) Uani d . 1 . . C C15 0.0781(2) 0.25244(19) 0.9711(2) 0.0350(6) Uani d . 1 . . H H15 0.1278 0.2466 1.0484 0.042 Uiso calc R 1 . . C C16 -0.0182(3) 0.3151(2) 0.9465(2) 0.0379(6) Uani d . 1 . . C C17 -0.0895(2) 0.3261(2) 0.8346(2) 0.0401(7) Uani d . 1 . . H H17 -0.1545 0.3701 0.8182 0.048 Uiso calc R 1 . . C C18 -0.0641(2) 0.2712(2) 0.7464(2) 0.0357(6) Uani d . 1 . . H H18 -0.1131 0.2784 0.6690 0.043 Uiso calc R 1 . . 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 Cl1 0.0422(4) 0.0492(4) 0.0331(4) 0.0138(3) -0.0011(3) 0.0054(3) Cl2 0.0770(6) 0.0613(5) 0.0364(4) 0.0174(4) 0.0203(4) -0.0056(4) O5 0.0346(10) 0.0656(14) 0.0307(11) -0.0077(9) -0.0021(8) -0.0049(9) O10 0.0555(13) 0.0543(13) 0.0520(13) -0.0192(11) 0.0084(11) 0.0061(11) O11 0.0494(11) 0.0390(11) 0.0382(11) 0.0014(9) 0.0067(9) 0.0104(9) N1 0.0335(12) 0.0443(14) 0.0275(12) -0.0053(10) -0.0037(10) 0.0045(10) C2 0.0289(13) 0.0358(14) 0.0344(15) -0.0026(11) 0.0063(11) -0.0038(12) C3 0.0316(13) 0.0319(13) 0.0313(14) -0.0004(11) 0.0073(11) -0.0025(11) C4 0.0288(13) 0.0338(14) 0.0246(13) 0.0032(11) 0.0015(10) -0.0012(11) C4A 0.0286(13) 0.0344(13) 0.0255(13) 0.0000(11) 0.0036(10) -0.0032(11) C5 0.0343(14) 0.0438(16) 0.0292(14) -0.0043(12) 0.0035(12) -0.0078(12) C6 0.0457(17) 0.064(2) 0.0395(17) -0.0250(15) 0.0023(14) -0.0011(15) C7A 0.069(4) 0.047(3) 0.029(3) -0.022(3) 0.002(3) 0.002(3) C19A 0.110(6) 0.075(5) 0.056(4) -0.036(4) -0.010(4) 0.010(4) C7B 0.049(3) 0.054(3) 0.036(3) -0.012(3) 0.013(2) 0.004(3) C19B 0.059(4) 0.071(4) 0.048(4) -0.020(3) 0.004(3) 0.020(3) C8 0.0426(16) 0.0443(16) 0.0295(14) -0.0040(13) 0.0024(12) 0.0052(12) C8A 0.0307(13) 0.0362(14) 0.0268(14) 0.0012(11) 0.0023(11) -0.0023(11) C9 0.0371(15) 0.0503(18) 0.0428(17) -0.0095(13) 0.0003(13) -0.0036(14) C10 0.0369(15) 0.0331(14) 0.0367(15) 0.0024(12) 0.0093(12) -0.0009(12) C12 0.063(2) 0.0442(17) 0.0438(18) 0.0044(15) 0.0161(15) 0.0138(14) C13 0.0339(13) 0.0316(13) 0.0255(13) 0.0004(11) 0.0067(10) 0.0029(11) C14 0.0322(13) 0.0333(14) 0.0299(14) 0.0027(11) 0.0038(11) 0.0050(11) C15 0.0430(15) 0.0379(15) 0.0220(13) -0.0004(12) 0.0050(11) 0.0048(11) C16 0.0481(16) 0.0370(15) 0.0315(14) 0.0016(13) 0.0157(12) -0.0009(12) C17 0.0397(15) 0.0435(16) 0.0371(16) 0.0081(13) 0.0104(12) 0.0026(13) C18 0.0347(14) 0.0415(15) 0.0283(14) 0.0071(12) 0.0039(11) 0.0017(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C14 1.741(3) ? Cl2 C16 1.737(3) ? O5 C5 1.242(3) yes O10 C10 1.208(3) yes O11 C10 1.355(3) yes O11 C12 1.440(3) ? N1 C8A 1.367(3) yes N1 C2 1.377(3) yes N1 H1 0.88(3) ? C2 C3 1.359(4) yes C2 C9 1.497(4) ? C3 C10 1.458(4) yes C3 C4 1.530(4) yes C4 C4A 1.515(4) yes C4 C13 1.534(3) ? C4 H4 1.0000 ? C4A C8A 1.356(3) yes C4A C5 1.444(4) ? C5 C6 1.503(4) ? C6 C7B 1.511(4) ? C6 C7A 1.537(4) ? C6 H61 0.9900 ? C6 H62 0.9900 ? C6 H63 0.9900 ? C6 H64 0.9900 ? C7A C8 1.505(4) ? C7A C19A 1.508(7) ? C7A H71 1.0000 ? C19A H191 0.9800 ? C19A H192 0.9800 ? C19A H193 0.9800 ? C7B C19B 1.508(6) ? C7B C8 1.523(4) ? C7B H72 1.0000 ? C19B H194 0.9800 ? C19B H195 0.9800 ? C19B H196 0.9800 ? C8 C8A 1.496(4) ? C8 H81 0.9900 ? C8 H82 0.9900 ? C8 H83 0.9900 ? C8 H84 0.9900 ? C9 H91 0.9800 ? C9 H92 0.9800 ? C9 H93 0.9800 ? C12 H121 0.9800 ? C12 H122 0.9800 ? C12 H123 0.9800 ? C13 C14 1.389(4) ? C13 C18 1.393(4) ? C14 C15 1.388(4) ? C15 C16 1.385(4) ? C15 H15 0.9500 ? C16 C17 1.377(4) ? C17 C18 1.388(4) ? C17 H17 0.9500 ? C18 H18 0.9500 ? 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 C10 O11 C12 115.6(2) ? C2 N1 C8A 123.3(2) yes C8A N1 H1 115(2) ? C2 N1 H1 122(2) ? N1 C2 C3 120.1(2) yes N1 C2 C9 113.1(2) yes C3 C2 C9 126.8(2) yes C2 C3 C10 119.8(2) yes C2 C3 C4 122.1(2) yes C10 C3 C4 118.1(2) ? C3 C4 C4A 110.7(2) yes C4A C4 C13 110.1(2) ? C3 C4 C13 111.6(2) ? C4A C4 H4 108.1 ? C3 C4 H4 108.1 ? C13 C4 H4 108.1 ? C8A C4A C5 119.0(2) ? C4 C4A C8A 122.7(2) yes C5 C4A C4 118.3(2) ? O5 C5 C4A 120.7(3) ? O5 C5 C6 120.3(2) ? C4A C5 C6 119.0(2) ? C5 C6 C7B 113.0(3) ? C5 C6 C7A 114.6(3) ? C5 C6 H61 108.6 ? C7A C6 H61 108.6 ? C5 C6 H62 108.6 ? C7A C6 H62 108.6 ? H61 C6 H62 107.6 ? C5 C6 H63 109.0 ? C7B C6 H63 109.0 ? C5 C6 H64 109.0 ? C7B C6 H64 109.0 ? H63 C6 H64 107.8 ? C8 C7A C19A 110.3(4) ? C8 C7A C6 108.3(3) ? C19A C7A C6 116.8(5) ? C8 C7A H71 107.0 ? C19A C7A H71 107.0 ? C6 C7A H71 107.0 ? C19B C7B C6 108.0(4) ? C19B C7B C8 114.7(4) ? C6 C7B C8 108.7(3) ? C19B C7B H72 108.4 ? C6 C7B H72 108.4 ? C8 C7B H72 108.4 ? C7B C19B H194 109.5 ? C7B C19B H195 109.5 ? H194 C19B H195 109.5 ? C7B C19B H196 109.5 ? H194 C19B H196 109.5 ? H195 C19B H196 109.5 ? C8A C8 C7A 113.1(3) ? C8A C8 C7B 110.6(3) ? C8A C8 H81 109.0 ? C7A C8 H81 109.0 ? C8A C8 H82 109.0 ? C7A C8 H82 109.0 ? H81 C8 H82 107.8 ? C8A C8 H83 109.5 ? C7B C8 H83 109.5 ? C8A C8 H84 109.5 ? C7B C8 H84 109.5 ? H83 C8 H84 108.1 ? N1 C8A C4A 120.3(2) yes C4A C8A C8 124.0(2) ? N1 C8A C8 115.7(2) ? C2 C9 H91 109.5 ? C2 C9 H92 109.5 ? H91 C9 H92 109.5 ? C2 C9 H93 109.5 ? H91 C9 H93 109.5 ? H92 C9 H93 109.5 ? O10 C10 O11 120.8(3) yes O10 C10 C3 128.0(3) yes O11 C10 C3 111.2(2) yes O11 C12 H121 109.5 ? O11 C12 H122 109.5 ? H121 C12 H122 109.5 ? O11 C12 H123 109.5 ? H121 C12 H123 109.5 ? H122 C12 H123 109.5 ? C14 C13 C18 116.9(2) ? C14 C13 C4 124.1(2) ? C18 C13 C4 119.0(2) ? C15 C14 C13 122.1(2) ? C15 C14 Cl1 116.0(2) ? C13 C14 Cl1 121.9(2) ? C16 C15 C14 118.7(2) ? C16 C15 H15 120.6 ? C14 C15 H15 120.6 ? C17 C16 C15 121.4(2) ? C17 C16 Cl2 120.3(2) ? C15 C16 Cl2 118.3(2) ? C16 C17 C18 118.4(3) ? C16 C17 H17 120.8 ? C18 C17 H17 120.8 ? C17 C18 C13 122.6(2) ? C17 C18 H18 118.7 ? C13 C18 H18 118.7 ? 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 C8A N1 C2 C3 3.5(4) C8A N1 C2 C9 -175.8(2) N1 C2 C3 C10 -176.7(2) C9 C2 C3 C10 2.5(4) N1 C2 C3 C4 3.3(4) C9 C2 C3 C4 -177.5(3) C2 C3 C4 C4A -8.9(3) C10 C3 C4 C4A 171.1(2) C2 C3 C4 C13 114.1(3) C10 C3 C4 C13 -65.8(3) C3 C4 C4A C8A 9.1(3) C13 C4 C4A C8A -114.8(3) C3 C4 C4A C5 -171.8(2) C13 C4 C4A C5 64.3(3) C8A C4A C5 O5 -179.0(3) C4 C4A C5 O5 1.9(4) C8A C4A C5 C6 1.1(4) C4 C4A C5 C6 -178.1(2) O5 C5 C6 C7B 151.2(3) C4A C5 C6 C7B -28.9(4) O5 C5 C6 C7A -153.9(3) C4A C5 C6 C7A 26.1(4) C5 C6 C7A C8 -50.4(5) C5 C6 C7A C19A -175.6(5) C5 C6 C7B C19B 179.4(5) C5 C6 C7B C8 54.4(5) C19A C7A C8 C8A 178.3(6) C6 C7A C8 C8A 49.4(5) C19B C7B C8 C8A -174.1(5) C6 C7B C8 C8A -53.2(4) C5 C4A C8A N1 177.3(2) C4 C4A C8A N1 -3.6(4) C5 C4A C8A C8 -1.3(4) C4 C4A C8A C8 177.9(2) C2 N1 C8A C4A -3.4(4) C2 N1 C8A C8 175.2(2) C7A C8 C8A C4A -26.0(4) C7B C8 C8A C4A 28.5(4) C7A C8 C8A N1 155.4(3) C7B C8 C8A N1 -150.1(3) C12 O11 C10 O10 -1.8(4) C12 O11 C10 C3 177.8(2) C2 C3 C10 O10 -2.7(4) C4 C3 C10 O10 177.3(3) C2 C3 C10 O11 177.7(2) C4 C3 C10 O11 -2.3(3) C4A C4 C13 C14 -115.5(3) C3 C4 C13 C14 121.0(3) C4A C4 C13 C18 63.7(3) C3 C4 C13 C18 -59.7(3) C18 C13 C14 C15 0.1(4) C4 C13 C14 C15 179.4(2) C18 C13 C14 Cl1 179.6(2) C4 C13 C14 Cl1 -1.2(4) C13 C14 C15 C16 0.9(4) Cl1 C14 C15 C16 -178.6(2) C14 C15 C16 C17 -1.5(4) C14 C15 C16 Cl2 178.5(2) C15 C16 C17 C18 1.2(4) Cl2 C16 C17 C18 -178.8(2) C16 C17 C18 C13 -0.1(4) C14 C13 C18 C17 -0.5(4) C4 C13 C18 C17 -179.8(2) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 O5 4_565 0.88(3) 1.96(3) 2.835(3) 173(3) yes _cod_database_code 2015279