#------------------------------------------------------------------------------ #$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $ #$Revision: 853 $ #$URL: svn://www.crystallography.net/cod/cif/2/2204516.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_2204516 _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 P21/n loop_ _publ_author_name 'M. Sukeri M. Yusof' 'Bohari M. Yamin' _publ_section_title ; N-(2-Bromophenyl)-N'-(4-methoxybenzoyl)thiourea ; _journal_issue 11 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o2045 _journal_page_last o2046 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C15 H13 Br N2 O2 S' _chemical_formula_moiety 'C15 H13 Br N2 O2 S' _chemical_formula_sum 'C15 H13 Br N2 O2 S' _chemical_formula_weight 365.24 _chemical_melting_point 433.9-435.0 _chemical_name_systematic ; N-(2-Bromophenyl)-N'-(4-methoxybenzoyl)thiourea ; _symmetry_cell_setting monoclinic _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 98.621(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.576(2) _cell_length_b 4.0362(6) _cell_length_c 27.495(4) _cell_measurement_reflns_used 1580 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.0 _cell_measurement_theta_min 1.5 _cell_volume 1489.6(4) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003) ; _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 88.66 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method \w _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 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 7392 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.0 _diffrn_reflns_theta_min 1.5 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.905 _exptl_absorpt_correction_T_max 0.772 _exptl_absorpt_correction_T_min 0.471 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.629 _exptl_crystal_density_method 'not measured' _exptl_crystal_description slab _exptl_crystal_F_000 736 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.328 _refine_diff_density_min -0.216 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.03 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 2891 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.03 _refine_ls_R_factor_all 0.066 _refine_ls_R_factor_gt 0.042 _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^)+(0.0489P)^2^+0.0218P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.091 _refine_ls_wR_factor_ref 0.100 _reflns_number_gt 2095 _reflns_number_total 2891 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file hg6091.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 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_type_symbol Br1 0.91691(3) 0.24916(10) 0.044550(14) 0.06425(17) Uani d . 1 Br S1 0.69119(6) 0.3320(2) 0.18377(3) 0.0464(2) Uani d . 1 S O1 1.00933(17) 0.6384(8) 0.17491(8) 0.0691(8) Uani d . 1 O O2 1.23825(16) 0.4963(7) 0.39155(8) 0.0621(7) Uani d . 1 O N1 0.87942(18) 0.4706(7) 0.21192(9) 0.0471(7) Uani d . 1 N H1A 0.8636 0.4152 0.2400 0.057 Uiso calc R 1 H N2 0.82544(18) 0.5545(7) 0.12959(9) 0.0473(7) Uani d . 1 N H2A 0.8864 0.6096 0.1289 0.057 Uiso calc R 1 H C1 1.0179(2) 0.3902(8) 0.30274(12) 0.0443(8) Uani d . 1 C H1B 0.9553 0.2949 0.3018 0.053 Uiso calc R 1 H C2 1.0838(2) 0.3820(9) 0.34541(12) 0.0486(8) Uani d . 1 C H2B 1.0657 0.2814 0.3732 0.058 Uiso calc R 1 H C3 1.1778(2) 0.5227(8) 0.34770(11) 0.0441(8) Uani d . 1 C C4 1.2045(2) 0.6731(8) 0.30663(12) 0.0451(8) Uani d . 1 C H4A 1.2671 0.7690 0.3078 0.054 Uiso calc R 1 H C5 1.1371(2) 0.6798(8) 0.26369(12) 0.0429(8) Uani d . 1 C H5A 1.1553 0.7817 0.2360 0.051 Uiso calc R 1 H C6 1.0432(2) 0.5393(8) 0.26056(11) 0.0379(7) Uani d . 1 C C7 0.9779(2) 0.5551(9) 0.21272(12) 0.0480(8) Uani d . 1 C C8 0.8023(2) 0.4610(8) 0.17318(11) 0.0395(7) Uani d . 1 C C9 0.7602(2) 0.5721(8) 0.08469(11) 0.0410(7) Uani d . 1 C C10 0.7901(2) 0.4484(8) 0.04176(11) 0.0442(8) Uani d . 1 C C11 0.7299(3) 0.4712(9) -0.00280(12) 0.0561(9) Uani d . 1 C H11A 0.7505 0.3848 -0.0310 0.067 Uiso calc R 1 H C12 0.6381(3) 0.6240(10) -0.00549(13) 0.0635(10) Uani d . 1 C H12A 0.5968 0.6423 -0.0356 0.076 Uiso calc R 1 H C13 0.6080(3) 0.7491(9) 0.03651(14) 0.0588(10) Uani d . 1 C H13A 0.5460 0.8502 0.0347 0.071 Uiso calc R 1 H C14 0.6685(2) 0.7256(8) 0.08067(12) 0.0483(8) Uani d . 1 C H14A 0.6476 0.8147 0.1086 0.058 Uiso calc R 1 H C15 1.3366(3) 0.6285(11) 0.39567(14) 0.0667(11) Uani d . 1 C H15A 1.3705 0.5951 0.4285 0.100 Uiso calc R 1 H H15B 1.3331 0.8613 0.3885 0.100 Uiso calc R 1 H H15C 1.3723 0.5180 0.3728 0.100 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 Br1 0.0535(2) 0.0776(3) 0.0662(3) 0.00495(19) 0.02389(19) -0.00403(19) S1 0.0375(4) 0.0600(6) 0.0429(5) -0.0049(4) 0.0103(4) 0.0035(4) O1 0.0454(14) 0.119(2) 0.0445(14) -0.0192(14) 0.0123(11) 0.0110(14) O2 0.0445(14) 0.092(2) 0.0482(15) -0.0065(13) 0.0018(11) 0.0054(13) N1 0.0366(14) 0.076(2) 0.0308(14) -0.0026(14) 0.0100(11) -0.0008(13) N2 0.0373(14) 0.067(2) 0.0380(15) -0.0068(14) 0.0083(12) 0.0019(14) C1 0.0327(16) 0.052(2) 0.050(2) -0.0006(15) 0.0126(15) 0.0020(16) C2 0.0431(19) 0.059(2) 0.046(2) -0.0009(16) 0.0143(16) 0.0081(16) C3 0.0364(17) 0.053(2) 0.044(2) 0.0029(15) 0.0087(15) -0.0013(16) C4 0.0344(16) 0.054(2) 0.049(2) -0.0048(15) 0.0121(15) -0.0045(15) C5 0.0381(17) 0.051(2) 0.0421(19) -0.0016(14) 0.0146(15) -0.0012(15) C6 0.0328(16) 0.0429(19) 0.0389(17) 0.0001(14) 0.0084(13) -0.0039(14) C7 0.0394(18) 0.059(2) 0.048(2) -0.0046(16) 0.0136(16) -0.0041(16) C8 0.0406(18) 0.044(2) 0.0349(17) 0.0000(14) 0.0088(14) -0.0041(14) C9 0.0384(17) 0.046(2) 0.0389(18) -0.0070(15) 0.0073(14) 0.0058(15) C10 0.0427(18) 0.048(2) 0.044(2) -0.0054(15) 0.0137(15) 0.0030(15) C11 0.070(2) 0.062(3) 0.037(2) -0.010(2) 0.0126(18) 0.0027(17) C12 0.066(3) 0.074(3) 0.047(2) -0.007(2) -0.0054(19) 0.0116(19) C13 0.051(2) 0.067(3) 0.056(2) 0.0050(19) 0.0009(18) 0.0104(19) C14 0.0493(19) 0.052(2) 0.045(2) 0.0029(16) 0.0109(16) 0.0037(15) C15 0.045(2) 0.094(3) 0.058(2) -0.009(2) -0.0028(18) -0.003(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Br1 C10 1.891(3) ? S1 C8 1.662(3) yes O1 C7 1.229(4) yes O2 C3 1.357(3) ? O2 C15 1.427(4) ? N1 C7 1.376(4) ? N1 C8 1.378(4) yes N1 H1A 0.8600 ? N2 C8 1.338(4) yes N2 C9 1.409(4) ? N2 H2A 0.8600 ? C1 C2 1.365(4) ? C1 C6 1.395(4) ? C1 H1B 0.9300 ? C2 C3 1.389(4) ? C2 H2B 0.9300 ? C3 C4 1.378(4) ? C4 C5 1.381(5) ? C4 H4A 0.9300 ? C5 C6 1.386(4) ? C5 H5A 0.9300 ? C6 C7 1.474(4) ? C9 C14 1.380(4) ? C9 C10 1.397(4) ? C10 C11 1.370(4) ? C11 C12 1.382(5) ? C11 H11A 0.9300 ? C12 C13 1.377(5) ? C12 H12A 0.9300 ? C13 C14 1.364(5) ? C13 H13A 0.9300 ? C14 H14A 0.9300 ? C15 H15A 0.9600 ? C15 H15B 0.9600 ? C15 H15C 0.9600 ? 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 C3 O2 C15 118.4(3) ? C7 N1 C8 130.0(3) ? C7 N1 H1A 115.0 ? C8 N1 H1A 115.0 ? C8 N2 C9 126.7(3) ? C8 N2 H2A 116.7 ? C9 N2 H2A 116.7 ? C2 C1 C6 120.9(3) ? C2 C1 H1B 119.6 ? C6 C1 H1B 119.6 ? C1 C2 C3 120.6(3) ? C1 C2 H2B 119.7 ? C3 C2 H2B 119.7 ? O2 C3 C4 124.4(3) ? O2 C3 C2 115.9(3) ? C4 C3 C2 119.7(3) ? C3 C4 C5 119.2(3) ? C3 C4 H4A 120.4 ? C5 C4 H4A 120.4 ? C4 C5 C6 122.0(3) ? C4 C5 H5A 119.0 ? C6 C5 H5A 119.0 ? C5 C6 C1 117.6(3) ? C5 C6 C7 117.6(3) ? C1 C6 C7 124.8(3) ? O1 C7 N1 120.9(3) yes O1 C7 C6 121.9(3) ? N1 C7 C6 117.2(3) ? N2 C8 N1 115.6(3) yes N2 C8 S1 125.9(2) yes N1 C8 S1 118.5(2) yes C14 C9 C10 117.8(3) ? C14 C9 N2 122.3(3) ? C10 C9 N2 119.9(3) ? C11 C10 C9 121.4(3) ? C11 C10 Br1 118.8(3) ? C9 C10 Br1 119.7(2) ? C10 C11 C12 119.3(3) ? C10 C11 H11A 120.3 ? C12 C11 H11A 120.3 ? C13 C12 C11 119.8(3) ? C13 C12 H12A 120.1 ? C11 C12 H12A 120.1 ? C14 C13 C12 120.4(4) ? C14 C13 H13A 119.8 ? C12 C13 H13A 119.8 ? C13 C14 C9 121.2(3) ? C13 C14 H14A 119.4 ? C9 C14 H14A 119.4 ? O2 C15 H15A 109.5 ? O2 C15 H15B 109.5 ? H15A C15 H15B 109.5 ? O2 C15 H15C 109.5 ? H15A C15 H15C 109.5 ? H15B C15 H15C 109.5 ? 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 C6 C1 C2 C3 0.0(5) C15 O2 C3 C4 -0.8(5) C15 O2 C3 C2 178.4(3) C1 C2 C3 O2 -178.9(3) C1 C2 C3 C4 0.3(5) O2 C3 C4 C5 178.8(3) C2 C3 C4 C5 -0.3(5) C3 C4 C5 C6 0.0(5) C4 C5 C6 C1 0.4(4) C4 C5 C6 C7 -178.9(3) C2 C1 C6 C5 -0.4(5) C2 C1 C6 C7 178.9(3) C8 N1 C7 O1 -0.1(6) C8 N1 C7 C6 -179.7(3) C5 C6 C7 O1 11.8(5) C1 C6 C7 O1 -167.4(3) C5 C6 C7 N1 -168.5(3) C1 C6 C7 N1 12.2(5) C9 N2 C8 N1 -178.9(3) C9 N2 C8 S1 2.1(5) C7 N1 C8 N2 -1.6(5) C7 N1 C8 S1 177.5(3) C8 N2 C9 C14 48.3(5) C8 N2 C9 C10 -135.4(3) C14 C9 C10 C11 -1.4(5) N2 C9 C10 C11 -177.8(3) C14 C9 C10 Br1 177.8(2) N2 C9 C10 Br1 1.4(4) C9 C10 C11 C12 0.9(5) Br1 C10 C11 C12 -178.3(3) C10 C11 C12 C13 -0.4(6) C11 C12 C13 C14 0.5(6) C12 C13 C14 C9 -1.1(5) C10 C9 C14 C13 1.5(5) N2 C9 C14 C13 177.8(3) 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 N2 H2A O1 1_555 0.86 1.94 2.640(3) 138 yes C14 H14A S1 1_555 0.93 2.84 3.224(3) 106 yes C1 H1B S1 2_645 0.93 2.80 3.686(3) 160 yes N1 H1A S1 2_655 0.86 2.87 3.478(3) 129 yes