#------------------------------------------------------------------------------ #$Date: 2020-02-08 02:47:32 +0200 (Sat, 08 Feb 2020) $ #$Revision: 247963 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/72/1557268.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_1557268 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 mixed _atom_sites_solution_primary iterative _audit_creation_date 2016-05-02 _audit_creation_method ; Olex2 1.2 (compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155) ; _cell_angle_alpha 64.386(5) _cell_angle_beta 71.962(4) _cell_angle_gamma 85.754(4) _cell_formula_units_Z 2 _cell_length_a 9.6678(5) _cell_length_b 12.9865(6) _cell_length_c 14.6942(7) _cell_measurement_reflns_used 8820 _cell_measurement_temperature 110.5(6) _cell_measurement_theta_max 71.5050 _cell_measurement_theta_min 3.4980 _cell_volume 1577.95(16) _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 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_temperature 110.5(6) _diffrn_detector_area_resol_mean 16.4335 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 35.00 61.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 57.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 2 omega -32.00 2.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 77.0000 90.0000 34 #__ type_ start__ end____ width___ exp.time_ 3 omega 6.00 70.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 77.0000 90.0000 64 #__ type_ start__ end____ width___ exp.time_ 4 omega -82.00 -46.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 178.0000 -180.0000 36 #__ type_ start__ end____ width___ exp.time_ 5 omega -127.00 -99.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -56.3168 -126.0000 0.0000 28 #__ type_ start__ end____ width___ exp.time_ 6 omega -128.00 -73.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -56.3168 -126.0000 -120.0000 55 #__ type_ start__ end____ width___ exp.time_ 7 omega 24.00 112.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 56.3168 -126.0000 120.0000 88 #__ type_ start__ end____ width___ exp.time_ 8 omega 7.00 99.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 56.3168 -95.0000 -60.0000 92 #__ type_ start__ end____ width___ exp.time_ 9 omega -13.00 73.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 56.3168 -61.0000 -180.0000 86 #__ type_ start__ end____ width___ exp.time_ 10 omega -17.00 128.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 56.3168 0.0000 0.0000 145 #__ type_ start__ end____ width___ exp.time_ 11 omega -34.00 -8.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -64.5000 50.0000 0.0000 26 #__ type_ start__ end____ width___ exp.time_ 12 omega -73.00 -38.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -64.5000 65.0000 -149.0000 35 #__ type_ start__ end____ width___ exp.time_ 13 omega -34.00 5.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -64.5000 25.0000 90.0000 39 #__ type_ start__ end____ width___ exp.time_ 14 omega 47.00 99.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -112.0000 30.0000 52 #__ type_ start__ end____ width___ exp.time_ 15 omega 39.00 114.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -112.0000 60.0000 75 #__ type_ start__ end____ width___ exp.time_ 16 omega 108.00 134.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 112.0000 150.0000 26 #__ type_ start__ end____ width___ exp.time_ 17 omega 42.00 92.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -38.0000 -120.0000 50 #__ type_ start__ end____ width___ exp.time_ 18 omega 40.00 93.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -38.0000 0.0000 53 #__ type_ start__ end____ width___ exp.time_ 19 omega 42.00 80.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -38.0000 150.0000 38 #__ type_ start__ end____ width___ exp.time_ 20 omega 40.00 120.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -77.0000 -120.0000 80 #__ type_ start__ end____ width___ exp.time_ 21 omega 55.00 93.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -25.0000 -90.0000 38 #__ type_ start__ end____ width___ exp.time_ 22 omega 48.00 92.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -112.0000 -120.0000 44 #__ type_ start__ end____ width___ exp.time_ 23 omega 88.00 173.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 50.0000 -180.0000 85 #__ type_ start__ end____ width___ exp.time_ 24 omega 58.00 91.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -25.0000 -180.0000 33 #__ type_ start__ end____ width___ exp.time_ 25 omega 79.00 105.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -112.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 26 omega 39.00 92.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -38.0000 60.0000 53 #__ type_ start__ end____ width___ exp.time_ 27 omega 44.00 89.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -25.0000 150.0000 45 #__ type_ start__ end____ width___ exp.time_ 28 omega 85.00 113.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -112.0000 -90.0000 28 #__ type_ start__ end____ width___ exp.time_ 29 omega 49.00 178.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -12.0000 -30.0000 129 #__ type_ start__ end____ width___ exp.time_ 30 omega 42.00 144.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -77.0000 60.0000 102 #__ type_ start__ end____ width___ exp.time_ 31 omega -82.00 -34.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 178.0000 -120.0000 48 #__ type_ start__ end____ width___ exp.time_ 32 omega -72.00 33.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -77.0000 120.0000 105 #__ type_ start__ end____ width___ exp.time_ 33 omega -129.00 -23.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -56.3168 -77.0000 -150.0000 106 #__ type_ start__ end____ width___ exp.time_ 34 omega -126.00 -31.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -56.3168 -61.0000 120.0000 95 #__ type_ start__ end____ width___ exp.time_ 35 omega -129.00 -23.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -56.3168 -77.0000 -60.0000 106 #__ type_ start__ end____ width___ exp.time_ 36 omega 23.00 129.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 56.3168 77.0000 90.0000 106 #__ type_ start__ end____ width___ exp.time_ 37 omega 29.00 127.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 56.3168 65.0000 30.0000 98 #__ type_ start__ end____ width___ exp.time_ 38 omega -3.00 99.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 56.3168 -95.0000 -90.0000 102 #__ type_ start__ end____ width___ exp.time_ 39 omega 40.00 138.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 -77.0000 60.0000 98 #__ type_ start__ end____ width___ exp.time_ 40 omega 81.00 178.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 38.0000 -30.0000 97 #__ type_ start__ end____ width___ exp.time_ 41 omega 68.00 178.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 25.0000 -90.0000 110 #__ type_ start__ end____ width___ exp.time_ 42 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_ 43 omega 40.00 178.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 112.6336 12.0000 90.0000 138 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0677924000 _diffrn_orient_matrix_UB_12 -0.1230894000 _diffrn_orient_matrix_UB_13 0.0731407000 _diffrn_orient_matrix_UB_21 0.1175159000 _diffrn_orient_matrix_UB_22 -0.0229408000 _diffrn_orient_matrix_UB_23 0.0559925000 _diffrn_orient_matrix_UB_31 -0.0990788000 _diffrn_orient_matrix_UB_32 0.0414081000 _diffrn_orient_matrix_UB_33 0.0803605000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_unetI/netI 0.0229 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.982 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 17629 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.982 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 71.734 _diffrn_reflns_theta_min 3.507 _diffrn_source 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.301 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.86520 _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 ; ; _exptl_crystal_density_diffrn 1.396 _exptl_crystal_description ; ; _exptl_crystal_F_000 690 _refine_diff_density_max 0.762 _refine_diff_density_min -0.836 _refine_diff_density_rms 0.060 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 430 _refine_ls_number_reflns 6054 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.065 _refine_ls_R_factor_all 0.0626 _refine_ls_R_factor_gt 0.0576 _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^)+(0.0554P)^2^+2.1970P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1411 _refine_ls_wR_factor_ref 0.1448 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5509 _reflns_number_total 6054 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file mp9b01178_si_002.cif _cod_data_source_block keto-paba-lt _cod_original_cell_volume 1577.95(15) _cod_database_code 1557268 _chemical_oxdiff_formula 'c26 h28 cl2 n4 o4' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _reflns_odcompleteness_completeness 99.86 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2. Uiso/Uaniso restraints and constraints Uanis(C13) = Uanis(C13A) Uanis(C14) = Uanis(C14A) Uanis(C12) = Uanis(C12A) 3. Others Sof(C13A)=1-FVAR(1) Sof(C13)=FVAR(1) Sof(C14A)=1-FVAR(2) Sof(C14)=FVAR(2) Sof(C12A)=1-FVAR(3) Sof(C12)=FVAR(3) 4.a Rotating group: N1B(H1BA,H1BB) 4.b Secondary CH2 refined with riding coordinates: C4(H4A,H4B), C23(H23A,H23B), C24(H24A,H24B), C21(H21A,H21B), C22(H22A,H22B) 4.c Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C16(H16), C1(H1), C3B(H3B), C2B(H2BA), C17(H17), C20(H20), C19(H19), C6B(H6B), C7(H7), C5B(H5B), C10(H10), C8(H8) 4.d Idealised Me refined as rotating group: C26(H26A,H26B,H26C) 4.e Idealised tetrahedral OH refined as rotating group: O2B(H2B) ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.15452(9) 0.97561(6) 0.82100(6) 0.0475(2) Uani 1 1 d . . . . Cl2 Cl 0.23039(10) 1.09787(8) 1.10488(7) 0.0618(3) Uani 1 1 d . . . . O3 O 0.70517(17) 0.60939(15) 0.79226(14) 0.0285(4) Uani 1 1 d . . . . O4 O 1.2545(2) 0.09889(18) 0.43463(16) 0.0408(5) Uani 1 1 d . . . . O1 O 0.3810(2) 0.66017(19) 0.9777(2) 0.0518(6) Uani 1 1 d . . . . O2 O 0.3744(2) 0.79586(18) 0.81970(16) 0.0431(5) Uani 1 1 d . . . . O2B O 0.6721(2) 0.57147(16) 0.34071(16) 0.0364(4) Uani 1 1 d . . . . H2B H 0.7071 0.5477 0.2956 0.055 Uiso 1 1 calc GR . . . O1B O 0.6667(3) 0.73216(18) 0.19895(16) 0.0489(5) Uani 1 1 d . . . . N2 N 0.1721(2) 0.59730(18) 0.91445(17) 0.0276(4) Uani 1 1 d . . . . N1 N 0.2209(2) 0.50854(19) 0.81062(18) 0.0315(5) Uani 1 1 d . . . . N4 N 1.0499(2) 0.1689(2) 0.50436(17) 0.0312(5) Uani 1 1 d . . . . N3 N 0.9104(2) 0.28871(19) 0.62842(16) 0.0283(4) Uani 1 1 d . . . . N1B N 0.3634(2) 0.8811(2) 0.57370(18) 0.0335(5) Uani 1 1 d . . . . H1BA H 0.3416 0.9488 0.5371 0.040 Uiso 1 1 d GR . . . H1BB H 0.2847 0.8396 0.6174 0.040 Uiso 1 1 d GR . . . C11 C 0.2152(3) 0.9391(2) 0.92990(19) 0.0276(5) Uani 1 1 d . . . . C15 C 0.7501(3) 0.5298(2) 0.75169(19) 0.0263(5) Uani 1 1 d . . . . C2 C 0.2178(3) 0.4317(2) 0.9113(2) 0.0320(5) Uani 1 1 d . . . . H2 H 0.2334 0.3544 0.9320 0.038 Uiso 1 1 calc R . . . C5 C 0.2955(3) 0.7462(2) 0.9297(2) 0.0303(5) Uani 1 1 d . . . . C3 C 0.1887(3) 0.4848(2) 0.9764(2) 0.0317(5) Uani 1 1 d . . . . H3 H 0.1814 0.4520 1.0480 0.038 Uiso 1 1 calc R . . . C25 C 1.1330(3) 0.1340(2) 0.4324(2) 0.0290(5) Uani 1 1 d . . . . C4 C 0.1504(3) 0.6894(2) 0.9482(2) 0.0283(5) Uani 1 1 d . . . . H4A H 0.0953 0.6587 1.0230 0.034 Uiso 1 1 calc R . . . H4B H 0.0940 0.7464 0.9090 0.034 Uiso 1 1 calc R . . . C6 C 0.2737(3) 0.8353(2) 0.97427(19) 0.0269(5) Uani 1 1 d . . . . C16 C 0.8920(3) 0.5007(2) 0.7401(2) 0.0299(5) Uani 1 1 d . . . . H16 H 0.9518 0.5332 0.7609 0.036 Uiso 1 1 calc R . . . C18 C 0.8606(3) 0.3719(2) 0.66673(19) 0.0272(5) Uani 1 1 d . . . . C1 C 0.1929(3) 0.6071(2) 0.8158(2) 0.0298(5) Uani 1 1 d . . . . H1 H 0.1881 0.6751 0.7586 0.036 Uiso 1 1 calc R . . . C4B C 0.5709(3) 0.7301(2) 0.3692(2) 0.0281(5) Uani 1 1 d . . . . C3B C 0.5300(3) 0.8424(2) 0.3295(2) 0.0295(5) Uani 1 1 d . . . . H3B H 0.5476 0.8840 0.2568 0.035 Uiso 1 1 calc R . . . C2B C 0.4637(3) 0.8930(2) 0.3964(2) 0.0289(5) Uani 1 1 d . . . . H2BA H 0.4375 0.9680 0.3682 0.035 Uiso 1 1 calc R . . . C17 C 0.9474(3) 0.4239(2) 0.6978(2) 0.0306(5) Uani 1 1 d . . . . H17 H 1.0442 0.4066 0.6899 0.037 Uiso 1 1 calc R . . . C1B C 0.4358(3) 0.8324(2) 0.5061(2) 0.0285(5) Uani 1 1 d . . . . C23 C 0.8975(3) 0.1945(3) 0.5176(2) 0.0355(6) Uani 1 1 d . . . . H23A H 0.8356 0.1299 0.5769 0.043 Uiso 1 1 calc R . . . H23B H 0.8742 0.2063 0.4542 0.043 Uiso 1 1 calc R . . . C24 C 0.8671(3) 0.3005(2) 0.5373(2) 0.0321(6) Uani 1 1 d . . . . H24A H 0.9205 0.3667 0.4746 0.038 Uiso 1 1 calc R . . . H24B H 0.7639 0.3126 0.5506 0.038 Uiso 1 1 calc R . . . C20 C 0.6607(3) 0.4789(3) 0.7223(2) 0.0379(6) Uani 1 1 d . . . . H20 H 0.5639 0.4966 0.7308 0.045 Uiso 1 1 calc R . . . C19 C 0.7162(3) 0.4020(3) 0.6804(2) 0.0389(6) Uani 1 1 d . . . . H19 H 0.6553 0.3691 0.6607 0.047 Uiso 1 1 calc R . . . C7B C 0.6412(3) 0.6801(2) 0.2941(2) 0.0317(6) Uani 1 1 d . . . . C26 C 1.0736(3) 0.1391(2) 0.3469(2) 0.0335(6) Uani 1 1 d . . . . H26A H 1.0677 0.2176 0.3005 0.050 Uiso 1 1 calc GR . . . H26B H 0.9782 0.1003 0.3789 0.050 Uiso 1 1 calc GR . . . H26C H 1.1372 0.1027 0.3068 0.050 Uiso 1 1 calc GR . . . C21 C 1.0642(3) 0.2663(3) 0.6121(2) 0.0352(6) Uani 1 1 d . . . . H21A H 1.0899 0.2559 0.6742 0.042 Uiso 1 1 calc R . . . H21B H 1.1234 0.3316 0.5518 0.042 Uiso 1 1 calc R . . . C6B C 0.4770(3) 0.7197(2) 0.5457(2) 0.0369(6) Uani 1 1 d . . . . H6B H 0.4593 0.6777 0.6184 0.044 Uiso 1 1 calc R . . . C22 C 1.0963(3) 0.1603(3) 0.5926(2) 0.0365(6) Uani 1 1 d . . . . H22A H 1.2001 0.1504 0.5771 0.044 Uiso 1 1 calc R . . . H22B H 1.0460 0.0936 0.6561 0.044 Uiso 1 1 calc R . . . C9 C 0.2457(3) 0.9952(2) 1.0561(2) 0.0396(7) Uani 1 1 d . . . . C7 C 0.3150(4) 0.8134(3) 1.0629(3) 0.0486(8) Uani 1 1 d . . . . H7 H 0.3530 0.7437 1.0952 0.058 Uiso 1 1 calc R . . . C5B C 0.5434(3) 0.6699(2) 0.4784(2) 0.0357(6) Uani 1 1 d . . . . H5B H 0.5702 0.5950 0.5065 0.043 Uiso 1 1 calc R . . . C10 C 0.2011(3) 1.0204(2) 0.9694(2) 0.0350(6) Uani 1 1 d . . . . H10 H 0.1625 1.0899 0.9379 0.042 Uiso 1 1 calc R . . . C13 C 0.5325(4) 0.6909(4) 0.8877(4) 0.0267(7) Uani 0.673(5) 1 d . P A 1 C8 C 0.3014(4) 0.8926(3) 1.1047(3) 0.0556(9) Uani 1 1 d . . . . H8 H 0.3293 0.8764 1.1643 0.067 Uiso 1 1 calc R . . . C12 C 0.5216(4) 0.8070(4) 0.8018(3) 0.0257(8) Uani 0.648(6) 1 d . P A 1 C14 C 0.5546(4) 0.5969(3) 0.8505(3) 0.0261(7) Uani 0.646(5) 1 d . P A 1 C13A C 0.5143(8) 0.6764(7) 0.9597(6) 0.0267(7) Uani 0.327(5) 1 d . P A 2 C14A C 0.5572(7) 0.6537(6) 0.7898(6) 0.0261(7) Uani 0.354(5) 1 d . P A 2 C12A C 0.5309(8) 0.7373(9) 0.8404(8) 0.0257(8) Uani 0.352(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 0.0663(5) 0.0402(4) 0.0476(4) -0.0172(3) -0.0356(4) 0.0040(3) Cl2 0.0724(6) 0.0638(5) 0.0651(5) -0.0524(5) -0.0008(4) -0.0175(4) O3 0.0202(8) 0.0370(9) 0.0358(9) -0.0237(8) -0.0070(7) 0.0022(7) O4 0.0358(10) 0.0505(12) 0.0509(12) -0.0346(10) -0.0177(9) 0.0200(9) O1 0.0457(12) 0.0502(12) 0.0954(18) -0.0501(13) -0.0464(12) 0.0249(10) O2 0.0272(9) 0.0576(13) 0.0503(12) -0.0411(10) 0.0096(8) -0.0109(8) O2B 0.0385(10) 0.0373(10) 0.0462(11) -0.0289(9) -0.0155(9) 0.0103(8) O1B 0.0673(15) 0.0380(11) 0.0371(11) -0.0225(9) -0.0011(10) 0.0036(10) N2 0.0201(10) 0.0332(11) 0.0381(11) -0.0238(9) -0.0080(8) 0.0021(8) N1 0.0263(11) 0.0379(12) 0.0428(12) -0.0268(10) -0.0136(9) 0.0038(9) N4 0.0262(11) 0.0441(12) 0.0347(11) -0.0261(10) -0.0124(9) 0.0082(9) N3 0.0234(10) 0.0410(12) 0.0317(11) -0.0240(9) -0.0124(8) 0.0088(9) N1B 0.0313(11) 0.0408(12) 0.0365(12) -0.0246(10) -0.0096(9) 0.0033(9) C11 0.0246(12) 0.0337(13) 0.0274(12) -0.0173(10) -0.0050(10) -0.0018(9) C15 0.0220(11) 0.0347(13) 0.0263(12) -0.0182(10) -0.0053(9) 0.0014(9) C2 0.0257(12) 0.0329(13) 0.0432(15) -0.0227(12) -0.0088(11) 0.0014(10) C5 0.0228(12) 0.0373(13) 0.0432(14) -0.0278(12) -0.0121(11) 0.0062(10) C3 0.0284(13) 0.0325(13) 0.0365(14) -0.0188(11) -0.0068(11) 0.0004(10) C25 0.0290(13) 0.0279(12) 0.0334(13) -0.0172(10) -0.0087(10) 0.0039(10) C4 0.0222(12) 0.0335(13) 0.0362(13) -0.0241(11) -0.0049(10) 0.0025(9) C6 0.0224(11) 0.0343(13) 0.0302(12) -0.0203(10) -0.0062(10) -0.0002(9) C16 0.0227(12) 0.0392(14) 0.0354(13) -0.0217(11) -0.0105(10) 0.0005(10) C18 0.0233(12) 0.0364(13) 0.0275(12) -0.0188(10) -0.0081(9) 0.0038(10) C1 0.0241(12) 0.0373(13) 0.0389(14) -0.0239(11) -0.0136(10) 0.0051(10) C4B 0.0225(11) 0.0307(12) 0.0367(13) -0.0204(11) -0.0076(10) -0.0003(9) C3B 0.0272(12) 0.0317(13) 0.0311(13) -0.0157(10) -0.0071(10) -0.0004(10) C2B 0.0268(12) 0.0273(12) 0.0364(13) -0.0173(10) -0.0096(10) 0.0027(9) C17 0.0194(11) 0.0419(14) 0.0387(14) -0.0244(12) -0.0103(10) 0.0053(10) C1B 0.0223(11) 0.0361(13) 0.0354(13) -0.0223(11) -0.0099(10) 0.0029(10) C23 0.0244(13) 0.0571(17) 0.0399(14) -0.0341(13) -0.0110(11) 0.0068(11) C24 0.0258(12) 0.0486(15) 0.0330(13) -0.0264(12) -0.0126(10) 0.0102(11) C20 0.0243(13) 0.0560(17) 0.0541(17) -0.0397(15) -0.0179(12) 0.0109(12) C19 0.0279(13) 0.0563(17) 0.0567(18) -0.0419(15) -0.0209(13) 0.0104(12) C7B 0.0250(12) 0.0346(13) 0.0412(15) -0.0232(12) -0.0065(11) -0.0017(10) C26 0.0330(13) 0.0407(14) 0.0320(13) -0.0227(11) -0.0070(11) 0.0038(11) C21 0.0294(13) 0.0485(16) 0.0460(15) -0.0323(13) -0.0206(12) 0.0131(11) C6B 0.0442(16) 0.0378(14) 0.0290(13) -0.0155(11) -0.0115(12) 0.0089(12) C22 0.0373(14) 0.0481(16) 0.0429(15) -0.0310(13) -0.0237(12) 0.0179(12) C9 0.0454(16) 0.0420(15) 0.0370(14) -0.0290(13) 0.0010(12) -0.0122(12) C7 0.074(2) 0.0398(16) 0.0511(18) -0.0238(14) -0.0395(17) 0.0078(15) C5B 0.0387(15) 0.0299(13) 0.0390(14) -0.0159(11) -0.0123(12) 0.0074(11) C10 0.0324(13) 0.0330(13) 0.0408(15) -0.0219(12) -0.0030(11) -0.0020(11) C13 0.0205(16) 0.0338(19) 0.0280(19) -0.0177(19) -0.0036(16) 0.0014(13) C8 0.088(3) 0.055(2) 0.0402(17) -0.0254(15) -0.0294(17) -0.0087(18) C12 0.0201(15) 0.030(2) 0.031(2) -0.0169(18) -0.0084(14) 0.0031(16) C14 0.0197(14) 0.034(2) 0.0312(19) -0.0205(15) -0.0080(15) 0.0064(14) C13A 0.0205(16) 0.0338(19) 0.0280(19) -0.0177(19) -0.0036(16) 0.0014(13) C14A 0.0197(14) 0.034(2) 0.0312(19) -0.0205(15) -0.0080(15) 0.0064(14) C12A 0.0201(15) 0.030(2) 0.031(2) -0.0169(18) -0.0084(14) 0.0031(16) 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 114.8(2) C15 O3 C14A 116.8(3) C5 O1 C13 102.5(3) C13A O1 C5 123.1(4) C5 O2 C12A 93.1(4) C12 O2 C5 112.1(2) C7B O2B H2B 109.5 C3 N2 C4 125.6(2) C1 N2 C3 107.0(2) C1 N2 C4 127.1(2) C1 N1 C2 105.3(2) C25 N4 C23 125.2(2) C25 N4 C22 121.0(2) C22 N4 C23 112.5(2) C18 N3 C24 115.3(2) C18 N3 C21 116.63(19) C21 N3 C24 110.59(19) H1BA N1B H1BB 109.4 C1B N1B H1BA 109.4 C1B N1B H1BB 109.2 C6 C11 Cl1 121.86(18) C6 C11 C10 122.4(2) C10 C11 Cl1 115.8(2) O3 C15 C20 123.9(2) C16 C15 O3 117.1(2) C16 C15 C20 118.9(2) N1 C2 H2 124.9 C3 C2 N1 110.3(2) C3 C2 H2 124.9 O1 C5 O2 105.2(2) O1 C5 C4 108.1(2) O1 C5 C6 110.7(2) O2 C5 C4 109.8(2) O2 C5 C6 111.1(2) C4 C5 C6 111.65(19) N2 C3 H3 127.1 C2 C3 N2 105.8(2) C2 C3 H3 127.1 O4 C25 N4 121.9(2) O4 C25 C26 120.1(2) N4 C25 C26 118.0(2) N2 C4 C5 111.45(19) N2 C4 H4A 109.3 N2 C4 H4B 109.3 C5 C4 H4A 109.3 C5 C4 H4B 109.3 H4A C4 H4B 108.0 C11 C6 C5 123.4(2) C11 C6 C7 117.2(2) C7 C6 C5 119.5(2) C15 C16 H16 119.4 C15 C16 C17 121.2(2) C17 C16 H16 119.4 C17 C18 N3 123.2(2) C19 C18 N3 120.3(2) C19 C18 C17 116.4(2) N2 C1 H1 124.2 N1 C1 N2 111.7(2) N1 C1 H1 124.2 C3B C4B C7B 118.9(2) C5B C4B C3B 118.2(2) C5B C4B C7B 122.9(2) C4B C3B H3B 119.4 C2B C3B C4B 121.2(2) C2B C3B H3B 119.4 C3B C2B H2BA 119.7 C3B C2B C1B 120.7(2) C1B C2B H2BA 119.7 C16 C17 C18 121.3(2) C16 C17 H17 119.3 C18 C17 H17 119.3 N1B C1B C2B 120.7(2) N1B C1B C6B 121.1(2) C2B C1B C6B 118.0(2) N4 C23 H23A 109.4 N4 C23 H23B 109.4 N4 C23 C24 111.1(2) H23A C23 H23B 108.0 C24 C23 H23A 109.4 C24 C23 H23B 109.4 N3 C24 C23 110.9(2) N3 C24 H24A 109.5 N3 C24 H24B 109.5 C23 C24 H24A 109.5 C23 C24 H24B 109.5 H24A C24 H24B 108.0 C15 C20 H20 120.1 C19 C20 C15 119.8(2) C19 C20 H20 120.1 C18 C19 H19 118.8 C20 C19 C18 122.4(2) C20 C19 H19 118.8 O2B C7B C4B 114.0(2) O1B C7B O2B 122.7(2) O1B C7B C4B 123.4(2) C25 C26 H26A 109.5 C25 C26 H26B 109.5 C25 C26 H26C 109.5 H26A C26 H26B 109.5 H26A C26 H26C 109.5 H26B C26 H26C 109.5 N3 C21 H21A 109.4 N3 C21 H21B 109.4 N3 C21 C22 111.1(2) H21A C21 H21B 108.0 C22 C21 H21A 109.4 C22 C21 H21B 109.4 C1B C6B H6B 119.5 C5B C6B C1B 121.0(2) C5B C6B H6B 119.5 N4 C22 C21 111.3(2) N4 C22 H22A 109.4 N4 C22 H22B 109.4 C21 C22 H22A 109.4 C21 C22 H22B 109.4 H22A C22 H22B 108.0 C10 C9 Cl2 118.2(2) C10 C9 C8 122.0(2) C8 C9 Cl2 119.8(2) C6 C7 H7 119.1 C6 C7 C8 121.8(3) C8 C7 H7 119.1 C4B C5B H5B 119.5 C6B C5B C4B 121.0(2) C6B C5B H5B 119.5 C11 C10 H10 121.0 C9 C10 C11 118.1(3) C9 C10 H10 121.0 C12 C13 O1 106.2(3) C12 C13 C14 113.0(4) C14 C13 O1 106.8(3) C9 C8 C7 118.6(3) C9 C8 H8 120.7 C7 C8 H8 120.7 O2 C12 C13 96.6(3) O3 C14 C13 105.1(3) O1 C13A C12A 88.6(5) O3 C14A C12A 107.1(5) C13A C12A O2 111.1(5) C14A C12A O2 103.9(5) C14A C12A C13A 112.0(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C11 1.736(2) Cl2 C9 1.746(3) O3 C15 1.385(3) O3 C14 1.421(4) O3 C14A 1.507(7) O4 C25 1.233(3) O1 C5 1.404(3) O1 C13 1.576(5) O1 C13A 1.248(7) O2 C5 1.421(3) O2 C12 1.371(4) O2 C12A 1.695(9) O2B H2B 0.8200 O2B C7B 1.333(3) O1B C7B 1.211(3) N2 C3 1.376(3) N2 C4 1.460(3) N2 C1 1.349(3) N1 C2 1.374(4) N1 C1 1.319(3) N4 C25 1.343(3) N4 C23 1.458(3) N4 C22 1.456(3) N3 C18 1.413(3) N3 C24 1.467(3) N3 C21 1.459(3) N1B H1BA 0.8610 N1B H1BB 0.8607 N1B C1B 1.387(3) C11 C6 1.385(4) C11 C10 1.390(3) C15 C16 1.374(3) C15 C20 1.390(3) C2 H2 0.9300 C2 C3 1.358(4) C5 C4 1.527(3) C5 C6 1.532(3) C3 H3 0.9300 C25 C26 1.512(3) C4 H4A 0.9700 C4 H4B 0.9700 C6 C7 1.386(4) C16 H16 0.9300 C16 C17 1.385(4) C18 C17 1.399(3) C18 C19 1.398(3) C1 H1 0.9300 C4B C3B 1.395(4) C4B C7B 1.480(3) C4B C5B 1.392(4) C3B H3B 0.9300 C3B C2B 1.383(3) C2B H2BA 0.9300 C2B C1B 1.398(4) C17 H17 0.9300 C1B C6B 1.401(4) C23 H23A 0.9700 C23 H23B 0.9700 C23 C24 1.516(4) C24 H24A 0.9700 C24 H24B 0.9700 C20 H20 0.9300 C20 C19 1.383(4) C19 H19 0.9300 C26 H26A 0.9600 C26 H26B 0.9600 C26 H26C 0.9600 C21 H21A 0.9700 C21 H21B 0.9700 C21 C22 1.516(4) C6B H6B 0.9300 C6B C5B 1.381(4) C22 H22A 0.9700 C22 H22B 0.9700 C9 C10 1.368(4) C9 C8 1.373(5) C7 H7 0.9300 C7 C8 1.389(4) C5B H5B 0.9300 C10 H10 0.9300 C13 C12 1.514(6) C13 C14 1.516(5) C8 H8 0.9300 C13A C12A 1.539(12) C14A C12A 1.528(10) 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 Cl1 C11 C6 C5 2.4(3) Cl1 C11 C6 C7 -178.2(2) Cl1 C11 C10 C9 179.2(2) Cl2 C9 C10 C11 179.2(2) Cl2 C9 C8 C7 -178.7(3) O3 C15 C16 C17 -178.5(2) O3 C15 C20 C19 178.7(3) O3 C14A C12A O2 172.7(5) O3 C14A C12A C13A -67.3(7) O1 C5 C4 N2 -52.8(3) O1 C5 C6 C11 168.9(2) O1 C5 C6 C7 -10.5(4) O1 C13 C12 O2 -29.9(3) O1 C13 C14 O3 -164.5(3) O1 C13A C12A O2 27.2(6) O1 C13A C12A C14A -88.5(6) O2 C5 C4 N2 61.5(3) O2 C5 C6 C11 52.4(3) O2 C5 C6 C7 -127.0(3) N1 C2 C3 N2 0.5(3) N4 C23 C24 N3 -55.2(3) N3 C18 C17 C16 -176.6(2) N3 C18 C19 C20 176.9(3) N3 C21 C22 N4 55.1(3) N1B C1B C6B C5B 177.2(2) C11 C6 C7 C8 -1.2(5) C15 O3 C14 C13 179.2(3) C15 O3 C14A C12A 178.8(5) C15 C16 C17 C18 -0.9(4) C15 C20 C19 C18 0.5(5) C2 N1 C1 N2 0.0(3) C5 O1 C13 C12 9.4(3) C5 O1 C13 C14 -111.5(3) C5 O1 C13A C12A -46.4(6) C5 O2 C12 C13 42.7(3) C5 O2 C12A C13A -6.3(6) C5 O2 C12A C14A 114.3(6) C5 C6 C7 C8 178.2(3) C3 N2 C4 C5 88.2(3) C3 N2 C1 N1 0.3(3) C25 N4 C23 C24 -139.0(3) C25 N4 C22 C21 138.5(3) C4 N2 C3 C2 -175.1(2) C4 N2 C1 N1 174.8(2) C4 C5 C6 C11 -70.6(3) C4 C5 C6 C7 110.0(3) C6 C11 C10 C9 -0.7(4) C6 C5 C4 N2 -174.8(2) C6 C7 C8 C9 -0.2(5) C16 C15 C20 C19 -1.1(4) C18 N3 C24 C23 -167.9(2) C18 N3 C21 C22 168.6(2) C1 N2 C3 C2 -0.5(3) C1 N2 C4 C5 -85.3(3) C1 N1 C2 C3 -0.3(3) C4B C3B C2B C1B -0.1(4) C3B C4B C7B O2B -178.2(2) C3B C4B C7B O1B 0.7(4) C3B C4B C5B C6B 0.2(4) C3B C2B C1B N1B -177.0(2) C3B C2B C1B C6B 0.0(4) C2B C1B C6B C5B 0.1(4) C17 C18 C19 C20 0.0(4) C1B C6B C5B C4B -0.3(4) C23 N4 C25 O4 -169.9(3) C23 N4 C25 C26 10.3(4) C23 N4 C22 C21 -53.8(3) C24 N3 C18 C17 -138.2(3) C24 N3 C18 C19 45.1(3) C24 N3 C21 C22 -57.0(3) C20 C15 C16 C17 1.4(4) C19 C18 C17 C16 0.2(4) C7B C4B C3B C2B 179.9(2) C7B C4B C5B C6B -179.7(2) C21 N3 C18 C17 -6.0(4) C21 N3 C18 C19 177.4(3) C21 N3 C24 C23 57.1(3) C22 N4 C25 O4 -3.8(4) C22 N4 C25 C26 176.5(2) C22 N4 C23 C24 53.9(3) C5B C4B C3B C2B -0.1(4) C5B C4B C7B O2B 1.8(3) C5B C4B C7B O1B -179.3(3) C10 C11 C6 C5 -177.7(2) C10 C11 C6 C7 1.7(4) C10 C9 C8 C7 1.2(5) C13 O1 C5 O2 14.9(2) C13 O1 C5 C4 132.3(2) C13 O1 C5 C6 -105.1(2) C8 C9 C10 C11 -0.8(4) C12 O2 C5 O1 -39.7(3) C12 O2 C5 C4 -155.9(2) C12 O2 C5 C6 80.1(3) C12 C13 C14 O3 79.0(4) C14 O3 C15 C16 -150.3(3) C14 O3 C15 C20 29.9(4) C14 C13 C12 O2 86.9(3) C13A O1 C5 O2 48.7(5) C13A O1 C5 C4 166.1(5) C13A O1 C5 C6 -71.3(5) C14A O3 C15 C16 171.3(4) C14A O3 C15 C20 -8.5(5) C12A O2 C5 O1 -15.9(3) C12A O2 C5 C4 -132.0(3) C12A O2 C5 C6 103.9(3)