#------------------------------------------------------------------------------ #$Date: 2020-02-08 02:47:44 +0200 (Sat, 08 Feb 2020) $ #$Revision: 247964 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/72/1557269.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1557269 loop_ _publ_author_name 'Martin, Flavia' 'Pop, Mihaela' 'Kacso, Irina' 'Grosu, Ioana Georgeta' 'Miclaus, Maria' 'Vodnar, Dan' 'Lung, Ildiko' 'Filip, Gabriela Adriana' 'Olteanu, Elena Diana' 'Moldovan, Remus' 'Nagy, Andras' 'Filip, Xenia' 'Baldea, Ioana' _publ_section_title ; Ketoconazole - p-aminobenzoic acid cocrystal: revival of an old drug by crystal engineering. ; _journal_name_full 'Molecular pharmaceutics' _journal_paper_doi 10.1021/acs.molpharmaceut.9b01178 _journal_year 2020 _chemical_formula_moiety 'C26 H23 Cl2 N4 O4, C7 H7 N O2' _chemical_formula_sum 'C33 H30 Cl2 N5 O6' _chemical_formula_weight 663.52 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2013-03-29 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _cell_angle_alpha 65.035(5) _cell_angle_beta 72.196(4) _cell_angle_gamma 84.857(4) _cell_formula_units_Z 2 _cell_length_a 9.7532(4) _cell_length_b 13.0997(6) _cell_length_c 14.7094(7) _cell_measurement_reflns_used 6615 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 70.4960 _cell_measurement_theta_min 3.8820 _cell_volume 1620.45(15) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.4335 _diffrn_measured_fraction_theta_full 0.9945 _diffrn_measured_fraction_theta_max 0.9945 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -24.00 8.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 57.0000 -180.0000 32 #__ type_ start__ end____ width___ exp.time_ 2 omega -80.00 -40.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 178.0000 0.0000 40 #__ type_ start__ end____ width___ exp.time_ 3 omega 27.00 71.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 57.0000 -180.0000 44 #__ type_ start__ end____ width___ exp.time_ 4 omega 7.00 56.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 57.0000 -90.0000 49 #__ type_ start__ end____ width___ exp.time_ 5 omega -128.00 -78.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -56.3168 -126.0000 -60.0000 50 #__ type_ start__ end____ width___ exp.time_ 6 omega -113.00 -87.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -56.3168 -95.0000 30.0000 26 #__ type_ start__ end____ width___ exp.time_ 7 omega -130.00 -87.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -56.3168 -95.0000 90.0000 43 #__ type_ start__ end____ width___ exp.time_ 8 omega 12.00 99.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 56.3168 -95.0000 0.0000 87 #__ type_ start__ end____ width___ exp.time_ 9 omega 23.00 118.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 56.3168 77.0000 -60.0000 95 #__ type_ start__ end____ width___ exp.time_ 10 omega 46.00 105.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 56.3168 -126.0000 -120.0000 59 #__ type_ start__ end____ width___ exp.time_ 11 omega -57.00 6.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -64.5000 50.0000 -150.0000 63 #__ type_ start__ end____ width___ exp.time_ 12 omega -132.00 -79.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -64.5000 -92.0000 -120.0000 53 #__ type_ start__ end____ width___ exp.time_ 13 omega -55.00 -21.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -64.5000 50.0000 -60.0000 34 #__ type_ start__ end____ width___ exp.time_ 14 omega -133.00 -35.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -64.5000 -77.0000 120.0000 98 #__ type_ start__ end____ width___ exp.time_ 15 omega 79.00 116.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -112.0000 -180.0000 37 #__ type_ start__ end____ width___ exp.time_ 16 omega 49.00 76.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -112.0000 -180.0000 27 #__ type_ start__ end____ width___ exp.time_ 17 omega 61.00 100.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -112.0000 -60.0000 39 #__ type_ start__ end____ width___ exp.time_ 18 omega 75.00 126.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 178.0000 -60.0000 51 #__ type_ start__ end____ width___ exp.time_ 19 omega 40.00 79.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -38.0000 -60.0000 39 #__ type_ start__ end____ width___ exp.time_ 20 omega 42.00 79.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -25.0000 60.0000 37 #__ type_ start__ end____ width___ exp.time_ 21 omega 39.00 88.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -25.0000 -30.0000 49 #__ type_ start__ end____ width___ exp.time_ 22 omega 59.00 101.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -112.0000 0.0000 42 #__ type_ start__ end____ width___ exp.time_ 23 omega 41.00 130.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -77.0000 81.0000 89 #__ type_ start__ end____ width___ exp.time_ 24 omega 59.00 85.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -38.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 25 omega 79.00 112.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -112.0000 60.0000 33 #__ type_ start__ end____ width___ exp.time_ 26 omega 40.00 93.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -38.0000 90.0000 53 #__ type_ start__ end____ width___ exp.time_ 27 omega 48.00 175.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 12.0000 0.0000 127 #__ type_ start__ end____ width___ exp.time_ 28 omega 49.00 106.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -64.0000 -30.0000 57 #__ type_ start__ end____ width___ exp.time_ 29 omega 96.00 177.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 50.0000 -120.0000 81 #__ type_ start__ end____ width___ exp.time_ 30 omega 56.00 82.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -38.0000 0.0000 26 #__ type_ start__ end____ width___ exp.time_ 31 omega 102.00 177.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 112.0000 0.0000 75 #__ type_ start__ end____ width___ exp.time_ 32 omega 41.00 104.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -50.0000 -120.0000 63 #__ type_ start__ end____ width___ exp.time_ 33 omega -72.00 33.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -77.0000 -27.0000 105 #__ type_ start__ end____ width___ exp.time_ 34 omega -82.00 -34.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 178.0000 60.0000 48 #__ type_ start__ end____ width___ exp.time_ 35 omega -82.00 -34.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 178.0000 -60.0000 48 #__ type_ start__ end____ width___ exp.time_ 36 omega -129.00 -23.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -56.3168 -77.0000 -180.0000 106 #__ type_ start__ end____ width___ exp.time_ 37 omega -126.00 -31.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -56.3168 -61.0000 30.0000 95 #__ type_ start__ end____ width___ exp.time_ 38 omega -129.00 -72.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -56.3168 -126.0000 0.0000 57 #__ type_ start__ end____ width___ exp.time_ 39 omega -55.00 16.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -56.3168 45.0000 -30.0000 71 #__ type_ start__ end____ width___ exp.time_ 40 omega 29.00 129.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 56.3168 45.0000 -90.0000 100 #__ type_ start__ end____ width___ exp.time_ 41 omega 23.00 129.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 56.3168 77.0000 0.0000 106 #__ type_ start__ end____ width___ exp.time_ 42 omega 80.00 178.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 77.0000 -30.0000 98 #__ type_ start__ end____ width___ exp.time_ 43 omega 80.00 178.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 77.0000 -120.0000 98 #__ type_ start__ end____ width___ exp.time_ 44 omega 86.00 178.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 64.0000 30.0000 92 #__ type_ start__ end____ width___ exp.time_ 45 omega 81.00 178.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 38.0000 -150.0000 97 #__ type_ start__ end____ width___ exp.time_ 46 omega 40.00 178.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 12.0000 150.0000 138 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0716370000 _diffrn_orient_matrix_UB_12 -0.0804628000 _diffrn_orient_matrix_UB_13 0.0823204000 _diffrn_orient_matrix_UB_21 0.0376093000 _diffrn_orient_matrix_UB_22 -0.0772010000 _diffrn_orient_matrix_UB_23 -0.0585143000 _diffrn_orient_matrix_UB_31 0.1450309000 _diffrn_orient_matrix_UB_32 0.0665524000 _diffrn_orient_matrix_UB_33 -0.0665930000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_unetI/netI 0.0289 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 17732 _diffrn_reflns_theta_full 71.91 _diffrn_reflns_theta_max 71.91 _diffrn_reflns_theta_min 3.47 _diffrn_source 'SuperNova (Cu) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _exptl_absorpt_coefficient_mu 2.241 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.75580 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 690 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.519 _refine_diff_density_min -0.461 _refine_diff_density_rms 0.051 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.636 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 426 _refine_ls_number_reflns 6206 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.636 _refine_ls_R_factor_all 0.0921 _refine_ls_R_factor_gt 0.0712 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2319 _refine_ls_wR_factor_ref 0.2489 _reflns_number_gt 4585 _reflns_number_total 6206 _reflns_threshold_expression >2sigma(I) _cod_data_source_file mp9b01178_si_003.cif _cod_data_source_block keto-paba _cod_original_cell_volume 1620.45(13) _cod_database_code 1557269 _chemical_oxdiff_formula 'c26 h28 cl2 n4 o4' _reflns_odcompleteness_completeness 99.45 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' 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 Cl1 Cl 0.66088(14) 0.47556(9) 0.31894(9) 0.0934(4) Uani 1 1 d . . . Cl2 Cl 0.73027(18) 0.59572(13) 0.60460(12) 0.1338(6) Uani 1 1 d . . . O3 O 1.2035(2) 0.10865(19) 0.29306(18) 0.0602(6) Uani 1 1 d . . . C15 C 1.2510(3) 0.0307(3) 0.2506(2) 0.0536(7) Uani 1 1 d . A . N3 N 1.4161(3) -0.2061(2) 0.1242(2) 0.0570(6) Uani 1 1 d . . . N2 N 0.6733(3) 0.0995(2) 0.4131(2) 0.0580(6) Uani 1 1 d . . . O2 O 0.8734(3) 0.2920(2) 0.3216(2) 0.0736(7) Uani 1 1 d . A . C17 C 1.4463(3) -0.0752(3) 0.1983(3) 0.0632(8) Uani 1 1 d . A . H17 H 1.5420 -0.0936 0.1922 0.076 Uiso 1 1 calc R . . N4 N 1.5530(3) -0.3277(3) 0.0021(2) 0.0662(7) Uani 1 1 d . . . N1 N 0.7191(3) 0.0105(3) 0.3106(3) 0.0681(8) Uani 1 1 d . A . C18 C 1.3638(3) -0.1247(3) 0.1639(2) 0.0524(7) Uani 1 1 d . . . O4 O 1.7548(3) -0.3946(2) -0.0695(2) 0.0872(8) Uani 1 1 d . . . O1 O 0.8800(3) 0.1597(2) 0.4785(3) 0.0872(9) Uani 1 1 d . . . C11 C 0.7177(3) 0.4392(3) 0.4287(2) 0.0564(7) Uani 1 1 d . . . C2 C 0.7154(4) -0.0644(3) 0.4109(3) 0.0677(9) Uani 1 1 d . A . H2 H 0.7297 -0.1411 0.4317 0.081 Uiso 1 1 calc R . . C16 C 1.3897(3) 0.0002(3) 0.2412(3) 0.0621(8) Uani 1 1 d . . . H16 H 1.4475 0.0308 0.2642 0.075 Uiso 1 1 calc R A . C5 C 0.7951(3) 0.2451(3) 0.4299(3) 0.0565(7) Uani 1 1 d . A . C19 C 1.2220(4) -0.0928(3) 0.1752(3) 0.0703(10) Uani 1 1 d . A . H19 H 1.1632 -0.1236 0.1530 0.084 Uiso 1 1 calc R . . C25 C 1.6340(4) -0.3629(3) -0.0694(3) 0.0602(8) Uani 1 1 d . . . C4 C 0.6529(3) 0.1920(3) 0.4462(3) 0.0597(8) Uani 1 1 d . . . H4A H 0.5982 0.1637 0.5200 0.072 Uiso 1 1 calc R A . H4B H 0.5976 0.2490 0.4067 0.072 Uiso 1 1 calc R . . C3 C 0.6881(4) -0.0106(3) 0.4744(3) 0.0638(8) Uani 1 1 d . . . H3 H 0.6809 -0.0421 0.5455 0.077 Uiso 1 1 calc R A . C24 C 1.3681(4) -0.1997(4) 0.0375(3) 0.0714(10) Uani 1 1 d . . . H24A H 1.4150 -0.1344 -0.0254 0.086 Uiso 1 1 calc R . . H24B H 1.2650 -0.1901 0.0536 0.086 Uiso 1 1 calc R . . C6 C 0.7725(3) 0.3343(3) 0.4744(2) 0.0536(7) Uani 1 1 d . . . C21 C 1.5682(4) -0.2278(4) 0.1067(3) 0.0747(11) Uani 1 1 d . . . H21A H 1.5955 -0.2365 0.1676 0.090 Uiso 1 1 calc R . . H21B H 1.6241 -0.1638 0.0467 0.090 Uiso 1 1 calc R . . C20 C 1.1654(4) -0.0173(3) 0.2178(3) 0.0710(10) Uani 1 1 d . . . H20 H 1.0697 0.0016 0.2247 0.085 Uiso 1 1 calc R A . C1 C 0.6941(4) 0.1086(3) 0.3156(3) 0.0639(8) Uani 1 1 d . . . H1 H 0.6912 0.1758 0.2586 0.077 Uiso 1 1 calc R A . C10 C 0.7041(4) 0.5186(3) 0.4687(3) 0.0717(10) Uani 1 1 d . . . H10 H 0.6672 0.5882 0.4366 0.086 Uiso 1 1 calc R A . C23 C 1.4017(4) -0.3039(4) 0.0171(3) 0.0818(12) Uani 1 1 d . . . H23A H 1.3438 -0.3676 0.0761 0.098 Uiso 1 1 calc R . . H23B H 1.3765 -0.2936 -0.0450 0.098 Uiso 1 1 calc R . . C22 C 1.6023(5) -0.3330(4) 0.0871(3) 0.0770(11) Uani 1 1 d . . . H22A H 1.7056 -0.3420 0.0702 0.092 Uiso 1 1 calc R . . H22B H 1.5565 -0.3983 0.1505 0.092 Uiso 1 1 calc R . . C9 C 0.7454(5) 0.4943(4) 0.5557(3) 0.0799(11) Uani 1 1 d . . . C26 C 1.5739(5) -0.3580(4) -0.1541(3) 0.0795(11) Uani 1 1 d . . . H26A H 1.4792 -0.3941 -0.1225 0.119 Uiso 1 1 calc R . . H26B H 1.6357 -0.3961 -0.1932 0.119 Uiso 1 1 calc R . . H26C H 1.5684 -0.2808 -0.2003 0.119 Uiso 1 1 calc R . . C7 C 0.8103(6) 0.3126(3) 0.5639(3) 0.0878(13) Uani 1 1 d . . . H7 H 0.8465 0.2432 0.5973 0.105 Uiso 1 1 calc R . . C14 C 1.0551(6) 0.0964(5) 0.3490(5) 0.0565(12) Uani 0.604(7) 1 d P A 1 C8 C 0.7954(6) 0.3929(4) 0.6053(3) 0.1028(16) Uani 1 1 d . . . H8 H 0.8198 0.3766 0.6662 0.123 Uiso 1 1 calc R A . O2B O 0.8327(3) 0.9275(2) 0.1610(2) 0.0770(7) Uani 1 1 d . . . H2B H 0.7990 0.9520 0.2058 0.116 Uiso 1 1 calc R . . N1B N 1.1392(4) 0.6174(3) -0.0710(3) 0.0755(8) Uani 1 1 d . . . H1BA H 1.1383 0.5456 -0.0354 0.091 Uiso 1 1 d R . . H1BB H 1.0959 0.6315 -0.1178 0.091 Uiso 1 1 d R . . C7B C 0.8607(4) 0.8203(3) 0.2066(3) 0.0655(9) Uani 1 1 d . . . C3B C 0.9729(4) 0.6585(3) 0.1707(3) 0.0627(8) Uani 1 1 d . . . H3B H 0.9553 0.6178 0.2427 0.075 Uiso 1 1 calc R . . C4B C 0.9325(3) 0.7693(3) 0.1321(3) 0.0566(7) Uani 1 1 d . . . C6B C 1.0276(4) 0.7776(3) -0.0418(3) 0.0719(10) Uani 1 1 d . . . H6B H 1.0460 0.8188 -0.1138 0.086 Uiso 1 1 calc R . . C1B C 1.0671(3) 0.6659(3) -0.0035(3) 0.0583(8) Uani 1 1 d . . . O1B O 0.8331(4) 0.7699(2) 0.3000(2) 0.1100(12) Uani 1 1 d . . . C2B C 1.0387(4) 0.6075(3) 0.1042(3) 0.0628(8) Uani 1 1 d . . . H2BA H 1.0643 0.5330 0.1321 0.075 Uiso 1 1 calc R . . C5B C 0.9621(4) 0.8282(3) 0.0247(3) 0.0690(9) Uani 1 1 d . . . H5B H 0.9373 0.9030 -0.0031 0.083 Uiso 1 1 calc R . . C14A C 1.0537(9) 0.1517(8) 0.2913(8) 0.0565(12) Uani 0.396(7) 1 d P A 2 C13 C 1.0304(4) 0.1984(4) 0.3789(4) 0.0567(11) Uani 0.691(6) 1 d P A 1 C12 C 1.0197(5) 0.2952(6) 0.3067(4) 0.1082(17) Uani 1 1 d . . . C13A C 1.0122(10) 0.1754(9) 0.4591(9) 0.0567(11) Uani 0.309(6) 1 d P A 2 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 Cl1 0.1214(10) 0.0796(6) 0.0954(7) -0.0318(5) -0.0630(7) 0.0123(6) Cl2 0.1548(14) 0.1344(11) 0.1464(12) -0.1123(10) -0.0010(10) -0.0359(9) O3 0.0469(13) 0.0727(13) 0.0765(14) -0.0474(12) -0.0158(11) 0.0042(10) C15 0.0453(18) 0.0670(17) 0.0590(17) -0.0362(14) -0.0155(14) 0.0038(13) N3 0.0468(15) 0.0784(16) 0.0631(15) -0.0437(13) -0.0217(12) 0.0123(12) N2 0.0476(16) 0.0642(15) 0.0749(17) -0.0418(13) -0.0164(13) 0.0019(12) O2 0.0510(15) 0.0946(17) 0.0834(16) -0.0615(14) 0.0087(12) -0.0121(12) C17 0.0389(18) 0.089(2) 0.081(2) -0.0525(19) -0.0196(16) 0.0077(15) N4 0.0554(18) 0.0910(19) 0.0735(17) -0.0540(16) -0.0222(14) 0.0144(14) N1 0.0618(18) 0.0773(18) 0.091(2) -0.0545(17) -0.0309(16) 0.0096(14) C18 0.0444(17) 0.0667(17) 0.0545(16) -0.0323(14) -0.0162(14) 0.0035(13) O4 0.078(2) 0.102(2) 0.103(2) -0.0666(17) -0.0304(16) 0.0363(16) O1 0.083(2) 0.0748(15) 0.141(2) -0.0636(17) -0.0633(19) 0.0273(14) C11 0.0503(19) 0.0594(16) 0.0595(17) -0.0290(14) -0.0084(14) -0.0034(13) C2 0.062(2) 0.0644(18) 0.090(2) -0.0451(18) -0.0208(19) 0.0002(15) C16 0.0434(18) 0.085(2) 0.077(2) -0.0514(18) -0.0180(16) 0.0021(15) C5 0.0470(18) 0.0634(17) 0.0728(19) -0.0409(15) -0.0187(15) 0.0056(13) C19 0.049(2) 0.100(3) 0.099(3) -0.070(2) -0.0341(19) 0.0163(18) C25 0.054(2) 0.0599(17) 0.0678(19) -0.0343(15) -0.0108(16) 0.0086(15) C4 0.0472(19) 0.0647(17) 0.077(2) -0.0439(16) -0.0100(16) 0.0011(14) C3 0.055(2) 0.0643(18) 0.073(2) -0.0341(16) -0.0108(17) -0.0022(15) C24 0.057(2) 0.107(3) 0.078(2) -0.061(2) -0.0294(18) 0.0221(19) C6 0.0521(19) 0.0582(16) 0.0557(16) -0.0311(13) -0.0113(14) -0.0010(13) C21 0.061(2) 0.104(3) 0.100(3) -0.072(2) -0.043(2) 0.029(2) C20 0.048(2) 0.097(2) 0.101(3) -0.067(2) -0.0331(19) 0.0174(17) C1 0.058(2) 0.074(2) 0.081(2) -0.0462(18) -0.0294(18) 0.0075(16) C10 0.073(3) 0.0579(18) 0.085(2) -0.0397(17) -0.008(2) -0.0039(16) C23 0.057(2) 0.129(3) 0.099(3) -0.085(3) -0.025(2) 0.015(2) C22 0.076(3) 0.096(3) 0.090(3) -0.060(2) -0.046(2) 0.037(2) C9 0.088(3) 0.082(2) 0.079(2) -0.054(2) 0.000(2) -0.022(2) C26 0.079(3) 0.101(3) 0.073(2) -0.057(2) -0.013(2) 0.007(2) C7 0.130(4) 0.073(2) 0.082(3) -0.035(2) -0.057(3) 0.004(2) C14 0.046(2) 0.068(3) 0.067(3) -0.042(3) -0.016(3) 0.011(2) C8 0.149(5) 0.110(4) 0.071(2) -0.047(2) -0.042(3) -0.020(3) O2B 0.087(2) 0.0710(14) 0.0924(17) -0.0505(14) -0.0331(16) 0.0189(13) N1B 0.080(2) 0.085(2) 0.083(2) -0.0517(17) -0.0316(18) 0.0133(16) C7B 0.059(2) 0.0629(18) 0.082(2) -0.0397(18) -0.0145(18) -0.0045(15) C3B 0.061(2) 0.0611(17) 0.0655(19) -0.0277(15) -0.0144(16) -0.0012(15) C4B 0.0483(18) 0.0599(16) 0.0710(19) -0.0362(15) -0.0164(15) -0.0018(13) C6B 0.086(3) 0.072(2) 0.064(2) -0.0316(17) -0.0288(19) 0.0136(18) C1B 0.0498(19) 0.0668(18) 0.0713(19) -0.0387(16) -0.0210(16) 0.0028(14) O1B 0.161(3) 0.0750(17) 0.0749(18) -0.0390(15) 0.0038(19) -0.0006(18) C2B 0.061(2) 0.0544(16) 0.075(2) -0.0302(15) -0.0179(17) 0.0039(14) C5B 0.080(3) 0.0590(17) 0.076(2) -0.0316(16) -0.032(2) 0.0119(16) C14A 0.046(2) 0.068(3) 0.067(3) -0.042(3) -0.016(3) 0.011(2) C13 0.028(2) 0.079(3) 0.086(3) -0.064(3) -0.005(2) 0.0003(17) C12 0.069(3) 0.174(6) 0.106(4) -0.090(4) -0.011(3) -0.004(3) C13A 0.028(2) 0.079(3) 0.086(3) -0.064(3) -0.005(2) 0.0003(17) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C15 O3 C14 114.5(3) C15 O3 C14A 116.5(4) C14 O3 C14A 33.6(4) C16 C15 O3 117.4(3) C16 C15 C20 118.7(3) C20 C15 O3 123.9(3) C18 N3 C24 116.1(2) C18 N3 C21 117.2(2) C21 N3 C24 111.3(2) C3 N2 C4 125.7(3) C1 N2 C4 126.6(3) C1 N2 C3 107.5(3) C12 O2 C5 111.5(3) C16 C17 C18 121.7(3) C25 N4 C23 125.1(3) C25 N4 C22 121.0(3) C22 N4 C23 112.7(3) C1 N1 C2 105.0(3) C17 C18 N3 123.3(3) C19 C18 N3 120.8(3) C19 C18 C17 115.9(3) C5 O1 C13 97.1(3) C13A O1 C5 121.9(6) C13A O1 C13 39.1(5) C6 C11 Cl1 121.3(2) C10 C11 Cl1 116.5(3) C10 C11 C6 122.1(3) C3 C2 N1 110.2(3) C15 C16 C17 121.2(3) O2 C5 C4 109.9(3) O2 C5 C6 111.0(3) O1 C5 O2 105.2(3) O1 C5 C4 108.5(3) O1 C5 C6 110.4(2) C4 C5 C6 111.4(2) C20 C19 C18 122.4(3) N4 C25 C26 118.1(3) O4 C25 N4 121.7(3) O4 C25 C26 120.1(3) N2 C4 C5 112.0(2) C2 C3 N2 105.9(3) N3 C24 C23 111.8(3) C11 C6 C5 123.8(3) C7 C6 C11 116.5(3) C7 C6 C5 119.7(3) N3 C21 C22 111.2(3) C19 C20 C15 120.0(3) N1 C1 N2 111.4(3) C9 C10 C11 119.2(3) N4 C23 C24 111.4(3) N4 C22 C21 111.4(3) C10 C9 Cl2 118.9(3) C8 C9 Cl2 119.6(3) C8 C9 C10 121.5(3) C6 C7 C8 121.5(4) O3 C14 C13 103.3(4) C9 C8 C7 119.2(4) O2B C7B C4B 114.2(3) O1B C7B O2B 122.5(3) O1B C7B C4B 123.3(3) C2B C3B C4B 121.3(3) C3B C4B C7B 119.4(3) C5B C4B C7B 122.6(3) C5B C4B C3B 118.0(3) C5B C6B C1B 121.4(3) N1B C1B C6B 121.0(3) N1B C1B C2B 121.3(3) C2B C1B C6B 117.6(3) C3B C2B C1B 120.8(3) C6B C5B C4B 120.8(3) O3 C14A C12 113.7(5) C14 C13 O1 103.1(4) C12 C13 O1 111.0(4) C12 C13 C14 117.2(5) O2 C12 C14A 95.3(4) C13 C12 O2 99.5(5) C13 C12 C14A 53.7(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C11 1.730(3) Cl2 C9 1.736(3) O3 C15 1.387(3) O3 C14 1.413(6) O3 C14A 1.522(9) C15 C16 1.358(4) C15 C20 1.386(4) N3 C18 1.409(3) N3 C24 1.456(4) N3 C21 1.449(4) N2 C4 1.463(3) N2 C3 1.364(4) N2 C1 1.340(4) O2 C5 1.418(4) O2 C12 1.378(5) C17 C18 1.394(4) C17 C16 1.376(4) N4 C25 1.334(4) N4 C23 1.449(4) N4 C22 1.445(4) N1 C2 1.375(5) N1 C1 1.315(4) C18 C19 1.389(4) O4 C25 1.213(4) O1 C5 1.403(4) O1 C13 1.658(6) O1 C13A 1.249(10) C11 C6 1.391(4) C11 C10 1.375(4) C2 C3 1.345(4) C5 C4 1.514(4) C5 C6 1.533(4) C19 C20 1.375(4) C25 C26 1.508(5) C24 C23 1.505(5) C6 C7 1.383(5) C21 C22 1.513(5) C10 C9 1.360(5) C9 C8 1.348(7) C7 C8 1.399(6) C14 C13 1.553(6) O2B C7B 1.321(4) N1B C1B 1.382(4) C7B C4B 1.484(4) C7B O1B 1.199(4) C3B C4B 1.387(4) C3B C2B 1.380(4) C4B C5B 1.381(5) C6B C1B 1.393(5) C6B C5B 1.376(4) C1B C2B 1.385(5) C14A C12 1.975(10) C13 C12 1.287(8)