#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/21/45/2214539.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_2214539 loop_ _publ_author_name 'B. Thimme Gowda' 'B. P. Sowmya' 'Miroslav Tokar\N-(3,4-Dichlorophenyl)benzamide ; _journal_coeditor_code BT2417 _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3365 _journal_page_last o3365 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C13 H9 Cl2 N O' _chemical_formula_moiety 'C13 H9 Cl2 N O' _chemical_formula_sum 'C13 H9 Cl2 N O' _chemical_formula_weight 266.11 _chemical_name_systematic ; N-(3,4-Dichlorophenyl)benzamide ; _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 difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 103.657(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.2828(2) _cell_length_b 5.14000(10) _cell_length_c 20.9368(5) _cell_measurement_reflns_used 7847 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 29.4796 _cell_measurement_theta_min 3.6018 _cell_volume 1179.87(4) _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2006)' _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2006)' _computing_data_reduction 'CrysAlis RED' _computing_molecular_graphics ; ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002) ; _computing_publication_material ; SHELXL97, PLATON (Spek, 2003) and WinGX (Farrugia, 1999) ; _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 295(2) _diffrn_detector_area_resol_mean 10.4340 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device '4-circle kappa geometry goniometer' _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur System' _diffrn_measurement_method '\w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 18488 _diffrn_reflns_theta_full 26.02 _diffrn_reflns_theta_max 26.02 _diffrn_reflns_theta_min 4.09 _diffrn_standards_decay_% 0.0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.530 _exptl_absorpt_correction_T_max 0.963 _exptl_absorpt_correction_T_min 0.811 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(CrysAlis RED; Oxford Diffraction, 2006)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 544 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.184 _refine_diff_density_min -0.239 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 2316 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.073 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0329 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.043P)^2^+0.3587P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0804 _refine_ls_wR_factor_ref 0.0932 _reflns_number_gt 1788 _reflns_number_total 2316 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bt2417.cif _[local]_cod_data_source_block I _[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. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2214539 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_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 C C1 -0.06707(16) 0.6618(3) 0.07436(9) 0.0408(4) Uani d . 1 C C2 -0.17812(16) 0.6102(3) 0.02116(9) 0.0403(4) Uani d . 1 C C3 -0.20601(19) 0.7783(4) -0.03154(10) 0.0517(5) Uani d . 1 H H3 -0.1533 0.9145 -0.0345 0.062 Uiso calc R 1 C C4 -0.3116(2) 0.7460(5) -0.07990(11) 0.0657(6) Uani d . 1 H H4 -0.3293 0.8602 -0.1153 0.079 Uiso calc R 1 C C5 -0.3899(2) 0.5489(5) -0.07623(11) 0.0650(6) Uani d . 1 H H5 -0.4607 0.5277 -0.1092 0.078 Uiso calc R 1 C C6 -0.3641(2) 0.3810(4) -0.02368(12) 0.0662(6) Uani d . 1 H H6 -0.4181 0.2474 -0.0208 0.079 Uiso calc R 1 C C7 -0.25851(19) 0.4096(4) 0.02470(11) 0.0557(5) Uani d . 1 H H7 -0.2411 0.2941 0.0599 0.067 Uiso calc R 1 C C8 0.07957(16) 0.4545(3) 0.16650(9) 0.0400(4) Uani d . 1 C C9 0.17486(16) 0.6320(3) 0.17660(9) 0.0437(4) Uani d . 1 H H9 0.1784 0.7555 0.1446 0.052 Uiso calc R 1 C C10 0.26459(16) 0.6244(3) 0.23455(9) 0.0446(4) Uani d . 1 C C11 0.25928(17) 0.4446(4) 0.28304(9) 0.0452(4) Uani d . 1 C C12 0.16527(18) 0.2642(4) 0.27169(10) 0.0498(5) Uani d . 1 H H12 0.1622 0.1393 0.3034 0.06 Uiso calc R 1 C C13 0.07682(17) 0.2684(4) 0.21419(9) 0.0455(4) Uani d . 1 H H13 0.0145 0.1457 0.2071 0.055 Uiso calc R 1 N N1 -0.01460(13) 0.4513(3) 0.10875(7) 0.0438(4) Uani d . 1 H H1 -0.0414 0.3012 0.0939 0.053 Uiso calc R 1 O O1 -0.02755(13) 0.8827(2) 0.08692(7) 0.0553(4) Uani d . 1 Cl Cl1 0.38564(5) 0.83887(10) 0.24432(3) 0.06298(19) Uani d . 1 Cl Cl2 0.36741(5) 0.43840(12) 0.35648(3) 0.0683(2) Uani d . 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 C1 0.0444(10) 0.0324(9) 0.0443(10) -0.0021(8) 0.0079(8) -0.0013(7) C2 0.0415(10) 0.0337(9) 0.0444(10) 0.0007(7) 0.0077(8) -0.0044(7) C3 0.0554(12) 0.0465(11) 0.0502(11) -0.0031(9) 0.0065(9) 0.0026(9) C4 0.0719(15) 0.0642(14) 0.0517(12) 0.0027(12) -0.0041(11) 0.0066(11) C5 0.0529(13) 0.0624(14) 0.0672(14) 0.0036(11) -0.0109(10) -0.0110(11) C6 0.0482(12) 0.0563(13) 0.0852(16) -0.0118(10) -0.0021(11) -0.0018(12) C7 0.0500(12) 0.0441(11) 0.0668(13) -0.0064(9) 0.0014(10) 0.0067(10) C8 0.0421(10) 0.0300(9) 0.0465(10) 0.0025(7) 0.0077(8) -0.0030(7) C9 0.0420(10) 0.0341(10) 0.0526(11) -0.0001(8) 0.0062(8) 0.0035(8) C10 0.0384(10) 0.0367(10) 0.0566(11) 0.0008(8) 0.0071(8) -0.0052(8) C11 0.0433(10) 0.0433(10) 0.0466(10) 0.0094(8) 0.0056(8) -0.0033(8) C12 0.0537(12) 0.0437(11) 0.0518(11) 0.0047(9) 0.0121(9) 0.0070(9) C13 0.0468(11) 0.0339(10) 0.0550(11) -0.0028(8) 0.0106(9) -0.0001(8) N1 0.0454(9) 0.0276(7) 0.0529(9) -0.0039(6) 0.0008(7) -0.0025(6) O1 0.0621(9) 0.0302(7) 0.0630(8) -0.0058(6) -0.0065(7) 0.0000(6) Cl1 0.0441(3) 0.0544(3) 0.0815(4) -0.0097(2) -0.0030(2) 0.0019(3) Cl2 0.0620(4) 0.0785(4) 0.0540(3) 0.0084(3) -0.0070(2) -0.0007(3) 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 O1 C1 N1 122.29(16) O1 C1 C2 121.63(16) N1 C1 C2 116.07(14) C3 C2 C7 118.71(17) C3 C2 C1 118.64(16) C7 C2 C1 122.51(16) C2 C3 C4 120.44(19) C2 C3 H3 119.8 C4 C3 H3 119.8 C5 C4 C3 120.6(2) C5 C4 H4 119.7 C3 C4 H4 119.7 C4 C5 C6 119.8(2) C4 C5 H5 120.1 C6 C5 H5 120.1 C5 C6 C7 120.3(2) C5 C6 H6 119.9 C7 C6 H6 119.9 C6 C7 C2 120.2(2) C6 C7 H7 119.9 C2 C7 H7 119.9 C9 C8 C13 119.44(16) C9 C8 N1 122.58(16) C13 C8 N1 117.97(16) C10 C9 C8 119.65(17) C10 C9 H9 120.2 C8 C9 H9 120.2 C11 C10 C9 120.79(17) C11 C10 Cl1 120.56(15) C9 C10 Cl1 118.63(14) C10 C11 C12 118.98(17) C10 C11 Cl2 121.52(15) C12 C11 Cl2 119.50(15) C13 C12 C11 120.59(18) C13 C12 H12 119.7 C11 C12 H12 119.7 C12 C13 C8 120.48(17) C12 C13 H13 119.8 C8 C13 H13 119.8 C1 N1 C8 126.38(14) C1 N1 H1 116.8 C8 N1 H1 116.8 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 O1 1.225(2) C1 N1 1.356(2) C1 C2 1.491(2) C2 C3 1.378(3) C2 C7 1.387(3) C3 C4 1.379(3) C3 H3 0.93 C4 C5 1.358(3) C4 H4 0.93 C5 C6 1.375(3) C5 H5 0.93 C6 C7 1.377(3) C6 H6 0.93 C7 H7 0.93 C8 C9 1.388(2) C8 C13 1.388(3) C8 N1 1.409(2) C9 C10 1.385(3) C9 H9 0.93 C10 C11 1.384(3) C10 Cl1 1.7293(18) C11 C12 1.387(3) C11 Cl2 1.7228(19) C12 C13 1.371(3) C12 H12 0.93 C13 H13 0.93 N1 H1 0.86 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 N1 H1 O1 1_545 0.86 2.16 2.9568(19) 153 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 O1 C1 C2 C3 28.3(3) N1 C1 C2 C3 -153.17(17) O1 C1 C2 C7 -147.4(2) N1 C1 C2 C7 31.1(3) C7 C2 C3 C4 -0.4(3) C1 C2 C3 C4 -176.28(18) C2 C3 C4 C5 0.3(3) C3 C4 C5 C6 0.4(4) C4 C5 C6 C7 -0.9(4) C5 C6 C7 C2 0.8(3) C3 C2 C7 C6 -0.1(3) C1 C2 C7 C6 175.59(19) C13 C8 C9 C10 -1.2(3) N1 C8 C9 C10 -179.99(16) C8 C9 C10 C11 -1.1(3) C8 C9 C10 Cl1 177.27(14) C9 C10 C11 C12 2.7(3) Cl1 C10 C11 C12 -175.68(14) C9 C10 C11 Cl2 -177.98(14) Cl1 C10 C11 Cl2 3.6(2) C10 C11 C12 C13 -1.9(3) Cl2 C11 C12 C13 178.72(15) C11 C12 C13 C8 -0.4(3) C9 C8 C13 C12 1.9(3) N1 C8 C13 C12 -179.20(17) O1 C1 N1 C8 8.0(3) C2 C1 N1 C8 -170.51(16) C9 C8 N1 C1 -37.6(3) C13 C8 N1 C1 143.61(18)