#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/32/2013272.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_2013272 loop_ _publ_author_name 'Parvez, Masood' 'Umbreen, Sumaira' 'Ansari, Farzana Latif' _publ_section_title ; Derivatives of 4-(2-hydroxylphenyl)-2-phenyl-2,3-dihydro-1,5-benzothiazepine ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o298 _journal_page_last o301 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C22 H19 N O2 S' _chemical_formula_moiety 'C22 H19 N O2 S' _chemical_formula_sum 'C22 H19 N O2 S' _chemical_formula_weight 361.44 _chemical_name_common ; ? ; _chemical_name_systematic ; 4-(2-hydroxylphenyl)-2-(4-methoxyphenyl)-2-phenyl-2,3-dihydro-1,5- benzothiazepine ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 94.437(9) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.973(2) _cell_length_b 16.224(4) _cell_length_c 9.250(3) _cell_measurement_reflns_used 7583 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 3.7 _cell_volume 1791.4(8) _computing_cell_refinement 'HKL DENZO (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SAPI91 (Fan, 1991)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Nonius KappaCCD Area Detector' _diffrn_measurement_method ' \w and \f ' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_av_sigmaI/netI 0.050 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 7583 _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 3.7 _exptl_absorpt_coefficient_mu 0.197 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_correction_T_min 0.908 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV: (Blessing, 1997)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 760 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.23 _refine_diff_density_min -0.36 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.02 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 237 _refine_ls_number_reflns 4081 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.02 _refine_ls_R_factor_all 0.064 _refine_ls_R_factor_gt 0.040 _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^)+(0.050P)^2^+0.404P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.095 _refine_ls_wR_factor_ref 0.107 _reflns_number_gt 3007 _reflns_number_total 4081 _reflns_threshold_expression 'I > 2.0\s(I)' _[local]_cod_data_source_file fr1416.cif _[local]_cod_data_source_block IVc _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2013272 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _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 _atom_site_type_symbol C1 0.69018(13) 0.08409(10) 0.37331(16) 0.0276(3) Uani d . 1 . . C C2 0.80306(13) 0.05878(10) 0.39202(16) 0.0298(4) Uani d . 1 . . C S3 0.91453(3) 0.12995(3) 0.42612(4) 0.03332(14) Uani d . 1 . . S C4 0.91081(12) 0.19439(10) 0.26106(15) 0.0258(3) Uani d . 1 . . C H4 0.9315 0.2517 0.2929 0.031 Uiso calc R 1 . . H C5 0.79075(12) 0.19788(10) 0.19215(15) 0.0254(3) Uani d . 1 . . C H5A 0.7869 0.2379 0.1111 0.031 Uiso calc R 1 . . H H5B 0.7699 0.1431 0.1515 0.031 Uiso calc R 1 . . H C6 0.70767(12) 0.22256(10) 0.29877(15) 0.0249(3) Uani d . 1 . . C N7 0.65848(10) 0.16807(8) 0.37436(13) 0.0270(3) Uani d . 1 . . N C8 0.60551(15) 0.02496(11) 0.36624(17) 0.0356(4) Uani d . 1 . . C H8 0.5294 0.0418 0.3535 0.043 Uiso calc R 1 . . H C9 0.63128(18) -0.05791(12) 0.37763(19) 0.0454(5) Uani d . 1 . . C H9 0.5730 -0.0978 0.3712 0.054 Uiso calc R 1 . . H C10 0.74195(18) -0.08290(12) 0.39839(19) 0.0450(5) Uani d . 1 . . C H10 0.7595 -0.1398 0.4082 0.054 Uiso calc R 1 . . H C11 0.82705(16) -0.02487(11) 0.40485(17) 0.0379(4) Uani d . 1 . . C H11 0.9028 -0.0425 0.4182 0.046 Uiso calc R 1 . . H C12 0.99582(13) 0.16724(9) 0.15730(16) 0.0256(3) Uani d . 1 . . C C13 0.96555(13) 0.12219(10) 0.03311(17) 0.0315(4) Uani d . 1 . . C H13 0.8897 0.1062 0.0119 0.038 Uiso calc R 1 . . H C14 1.04633(14) 0.10037(11) -0.06055(17) 0.0353(4) Uani d . 1 . . C H14 1.0250 0.0698 -0.1459 0.042 Uiso calc R 1 . . H C15 1.15660(14) 0.12261(11) -0.03077(18) 0.0336(4) Uani d . 1 . . C H15 1.2111 0.1078 -0.0956 0.040 Uiso calc R 1 . . H C16 1.18799(13) 0.16686(10) 0.09443(17) 0.0304(4) Uani d . 1 . . C C17 1.10791(13) 0.18948(10) 0.18856(17) 0.0285(3) Uani d . 1 . . C H17 1.1294 0.2200 0.2739 0.034 Uiso calc R 1 . . H C18 0.68103(12) 0.30969(10) 0.32035(15) 0.0259(3) Uani d . 1 . . C C19 0.73321(14) 0.37229(10) 0.24504(17) 0.0317(4) Uani d . 1 . . C H19 0.7819 0.3574 0.1730 0.038 Uiso calc R 1 . . H C20 0.71591(14) 0.45478(11) 0.27241(18) 0.0360(4) Uani d . 1 . . C H20 0.7521 0.4959 0.2199 0.043 Uiso calc R 1 . . H C21 0.64493(15) 0.47677(11) 0.37760(19) 0.0382(4) Uani d . 1 . . C H21 0.6335 0.5334 0.3983 0.046 Uiso calc R 1 . . H C22 0.59088(14) 0.41730(11) 0.45220(18) 0.0356(4) Uani d . 1 . . C H22 0.5420 0.4333 0.5233 0.043 Uiso calc R 1 . . H C23 0.60698(13) 0.33411(10) 0.42478(16) 0.0290(4) Uani d . 1 . . C O24 0.55363(10) 0.27899(8) 0.50447(12) 0.0354(3) Uani d . 1 . . O H24 0.5718 0.2310 0.4815 0.053 Uiso calc R 1 . . H O25 1.29948(9) 0.18624(8) 0.11383(13) 0.0420(3) Uani d . 1 . . O C26 1.34418(15) 0.21132(12) 0.2539(2) 0.0410(4) Uani d . 1 . . C H26A 1.4257 0.2171 0.2541 0.049 Uiso calc R 1 . . H H26B 1.3264 0.1698 0.3255 0.049 Uiso calc R 1 . . H H26C 1.3113 0.2643 0.2785 0.049 Uiso calc R 1 . . H 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 C1 0.0303(8) 0.0327(9) 0.0200(7) 0.0024(7) 0.0025(6) 0.0013(6) C2 0.0323(9) 0.0374(9) 0.0198(7) 0.0056(7) 0.0039(6) 0.0015(6) S3 0.0248(2) 0.0517(3) 0.0231(2) 0.00411(18) -0.00084(15) 0.00421(17) C4 0.0238(8) 0.0320(8) 0.0218(7) 0.0020(6) 0.0027(6) -0.0022(6) C5 0.0247(8) 0.0316(8) 0.0200(7) 0.0040(6) 0.0021(6) -0.0010(6) C6 0.0214(7) 0.0337(9) 0.0192(7) 0.0026(6) -0.0016(5) 0.0001(6) N7 0.0227(7) 0.0332(7) 0.0248(6) 0.0028(5) 0.0015(5) 0.0008(6) C8 0.0365(10) 0.0405(10) 0.0299(9) -0.0035(8) 0.0021(7) 0.0006(7) C9 0.0627(13) 0.0383(11) 0.0352(10) -0.0119(9) 0.0040(8) -0.0031(8) C10 0.0713(14) 0.0326(10) 0.0317(9) 0.0079(9) 0.0081(9) 0.0006(8) C11 0.0459(11) 0.0417(10) 0.0267(8) 0.0149(8) 0.0061(7) 0.0014(7) C12 0.0254(8) 0.0268(8) 0.0250(8) 0.0033(6) 0.0044(6) 0.0003(6) C13 0.0268(8) 0.0390(10) 0.0288(8) 0.0006(7) 0.0029(6) -0.0066(7) C14 0.0376(10) 0.0414(10) 0.0271(8) 0.0045(8) 0.0038(7) -0.0075(7) C15 0.0341(9) 0.0390(10) 0.0291(8) 0.0062(7) 0.0119(7) 0.0006(7) C16 0.0255(8) 0.0336(9) 0.0327(9) 0.0001(7) 0.0074(6) 0.0029(7) C17 0.0280(8) 0.0312(9) 0.0266(8) -0.0006(7) 0.0040(6) -0.0033(7) C18 0.0224(8) 0.0331(9) 0.0217(7) 0.0067(6) -0.0010(6) 0.0011(6) C19 0.0334(9) 0.0354(9) 0.0264(8) 0.0038(7) 0.0034(6) 0.0010(7) C20 0.0373(9) 0.0331(9) 0.0377(9) 0.0028(7) 0.0036(7) 0.0041(7) C21 0.0390(10) 0.0326(9) 0.0422(10) 0.0099(8) -0.0015(8) -0.0027(8) C22 0.0327(9) 0.0400(10) 0.0345(9) 0.0118(7) 0.0049(7) -0.0039(8) C23 0.0234(8) 0.0386(9) 0.0248(8) 0.0050(7) 0.0004(6) 0.0019(7) O24 0.0312(6) 0.0401(7) 0.0362(6) 0.0060(5) 0.0122(5) 0.0017(5) O25 0.0250(6) 0.0590(8) 0.0432(7) -0.0044(6) 0.0102(5) -0.0079(6) C26 0.0275(9) 0.0489(11) 0.0464(11) -0.0025(8) 0.0014(8) 0.0012(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C8 . 1.394(2) n C1 C2 . 1.410(2) n C1 N7 . 1.414(2) y C2 C11 . 1.390(2) n C2 S3 . 1.775(2) y S3 C4 . 1.848(2) y C4 C12 . 1.517(2) n C4 C5 . 1.528(2) n C4 H4 . 1.0000 n C5 C6 . 1.508(2) n C5 H5A . 0.9900 n C5 H5B . 0.9900 n C6 N7 . 1.297(2) y C6 C18 . 1.466(2) n C8 C9 . 1.382(3) n C8 H8 . 0.9500 n C9 C10 . 1.385(3) n C9 H9 . 0.9500 n C10 C11 . 1.385(3) n C10 H10 . 0.9500 n C11 H11 . 0.9500 n C12 C13 . 1.386(2) n C12 C17 . 1.398(2) n C13 C14 . 1.393(2) n C13 H13 . 0.9500 n C14 C15 . 1.376(2) n C14 H14 . 0.9500 n C15 C16 . 1.389(2) n C15 H15 . 0.9500 n C16 O25 . 1.370(2) n C16 C17 . 1.393(2) n C17 H17 . 0.9500 n C18 C19 . 1.405(2) n C18 C23 . 1.417(2) n C19 C20 . 1.381(2) n C19 H19 . 0.9500 n C20 C21 . 1.387(2) n C20 H20 . 0.9500 n C21 C22 . 1.377(3) n C21 H21 . 0.9500 n C22 C23 . 1.390(2) n C22 H22 . 0.9500 n C23 O24 . 1.351(2) y O24 H24 . 0.8400 n O25 C26 . 1.422(2) n C26 H26A . 0.9800 n C26 H26B . 0.9800 n C26 H26C . 0.9800 n 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 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 _geom_angle_publ_flag C8 C1 C2 119.47(15) n C8 C1 N7 117.96(14) n C2 C1 N7 122.32(14) n C11 C2 C1 118.97(16) n C11 C2 S3 118.19(13) n C1 C2 S3 122.19(13) n C2 S3 C4 104.57(7) y C12 C4 C5 113.73(12) n C12 C4 S3 112.57(10) n C5 C4 S3 109.11(10) n C12 C4 H4 107.0 n C5 C4 H4 107.0 n S3 C4 H4 107.0 n C6 C5 C4 112.58(12) n C6 C5 H5A 109.1 n C4 C5 H5A 109.1 n C6 C5 H5B 109.1 n C4 C5 H5B 109.1 n H5A C5 H5B 107.8 n N7 C6 C18 118.12(14) n N7 C6 C5 121.45(14) n C18 C6 C5 120.43(14) n C6 N7 C1 121.32(13) y C9 C8 C1 120.60(17) n C9 C8 H8 119.7 n C1 C8 H8 119.7 n C8 C9 C10 120.08(18) n C8 C9 H9 120.0 n C10 C9 H9 120.0 n C9 C10 C11 119.98(17) n C9 C10 H10 120.0 n C11 C10 H10 120.0 n C2 C11 C10 120.89(17) n C2 C11 H11 119.6 n C10 C11 H11 119.6 n C13 C12 C17 119.52(14) n C13 C12 C4 122.16(14) n C17 C12 C4 118.32(13) n C12 C13 C14 119.99(15) n C12 C13 H13 120.0 n C14 C13 H13 120.0 n C15 C14 C13 120.70(15) n C15 C14 H14 119.7 n C13 C14 H14 119.7 n C14 C15 C16 119.73(15) n C14 C15 H15 120.1 n C16 C15 H15 120.1 n O25 C16 C17 124.64(15) n O25 C16 C15 115.20(14) n C17 C16 C15 120.14(15) n C16 C17 C12 119.91(14) n C16 C17 H17 120.0 n C12 C17 H17 120.0 n C19 C18 C23 117.48(15) n C19 C18 C6 121.31(14) n C23 C18 C6 121.09(14) n C20 C19 C18 122.08(15) n C20 C19 H19 119.0 n C18 C19 H19 119.0 n C19 C20 C21 119.12(16) n C19 C20 H20 120.4 n C21 C20 H20 120.4 n C22 C21 C20 120.57(16) n C22 C21 H21 119.7 n C20 C21 H21 119.7 n C21 C22 C23 120.80(16) n C21 C22 H22 119.6 n C23 C22 H22 119.6 n O24 C23 C22 117.73(14) n O24 C23 C18 122.29(15) n C22 C23 C18 119.92(15) n C23 O24 H24 109.5 n C16 O25 C26 118.63(13) n O25 C26 H26A 109.5 n O25 C26 H26B 109.5 n H26A C26 H26B 109.5 n O25 C26 H26C 109.5 n H26A C26 H26C 109.5 n H26B C26 H26C 109.5 n loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O24 H24 N7 0.84 1.81 2.5489(18) 147 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 C8 C1 C2 C11 -0.8(2) n N7 C1 C2 C11 173.35(14) n C8 C1 C2 S3 -171.44(12) n N7 C1 C2 S3 2.7(2) n C11 C2 S3 C4 125.51(12) n C1 C2 S3 C4 -63.79(13) n C2 S3 C4 C12 -98.63(12) n C2 S3 C4 C5 28.61(12) n C12 C4 C5 C6 178.28(13) n S3 C4 C5 C6 51.70(15) n C4 C5 C6 N7 -90.11(17) n C4 C5 C6 C18 89.42(16) n C18 C6 N7 C1 -171.87(12) n C5 C6 N7 C1 7.7(2) n C8 C1 N7 C6 -137.86(15) n C2 C1 N7 C6 47.9(2) n C2 C1 C8 C9 0.1(2) n N7 C1 C8 C9 -174.31(14) n C1 C8 C9 C10 0.9(2) n C8 C9 C10 C11 -1.3(3) n C1 C2 C11 C10 0.5(2) n S3 C2 C11 C10 171.49(13) n C9 C10 C11 C2 0.6(2) n C5 C4 C12 C13 -22.2(2) n S3 C4 C12 C13 102.57(15) n C5 C4 C12 C17 157.21(14) n S3 C4 C12 C17 -78.05(16) n C17 C12 C13 C14 -0.9(2) n C4 C12 C13 C14 178.49(15) n C12 C13 C14 C15 0.4(3) n C13 C14 C15 C16 0.4(3) n C14 C15 C16 O25 -179.76(15) n C14 C15 C16 C17 -0.8(3) n O25 C16 C17 C12 179.20(15) n C15 C16 C17 C12 0.3(2) n C13 C12 C17 C16 0.5(2) n C4 C12 C17 C16 -178.90(14) n N7 C6 C18 C19 178.34(14) n C5 C6 C18 C19 -1.2(2) n N7 C6 C18 C23 2.4(2) n C5 C6 C18 C23 -177.14(13) n C23 C18 C19 C20 1.4(2) n C6 C18 C19 C20 -174.72(14) n C18 C19 C20 C21 0.1(3) n C19 C20 C21 C22 -1.1(3) n C20 C21 C22 C23 0.6(3) n C21 C22 C23 O24 178.32(15) n C21 C22 C23 C18 0.9(2) n C19 C18 C23 O24 -179.13(14) n C6 C18 C23 O24 -3.0(2) n C19 C18 C23 C22 -1.8(2) n C6 C18 C23 C22 174.26(14) n C17 C16 O25 C26 17.6(2) n C15 C16 O25 C26 -163.49(15) n _cod_database_fobs_code 2013272