#------------------------------------------------------------------------------ #$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2218142.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_2218142 loop_ _publ_author_name 'Saeed, Aamer' 'Abbas, Naeem' 'Hussain, Shahid' 'Fl\"orke, Ulrich' _publ_section_title ; 2,4-Dichloro-N-cyclohexylbenzamide ; _journal_coeditor_code HK2439 _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o773 _journal_volume 64 _journal_year 2008 _chemical_formula_iupac 'C13 H15 Cl2 N O' _chemical_formula_moiety 'C13 H15 Cl2 N O' _chemical_formula_sum 'C13 H15 Cl2 N O' _chemical_formula_weight 272.16 _chemical_name_systematic ; 2,4-Dichloro-N-cyclohexylbenzamide ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 90.167(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 26.135(3) _cell_length_b 4.9144(6) _cell_length_c 20.449(2) _cell_measurement_reflns_used 978 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 25.92 _cell_measurement_theta_min 2.51 _cell_volume 2626.4(5) _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_collection 'SMART (Bruker, 2002)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_molecular_graphics 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0443 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 10950 _diffrn_reflns_theta_full 27.86 _diffrn_reflns_theta_max 27.86 _diffrn_reflns_theta_min 1.56 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 430 _diffrn_standards_number 1956 _exptl_absorpt_coefficient_mu 0.477 _exptl_absorpt_correction_T_max 0.9449 _exptl_absorpt_correction_T_min 0.8033 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1136 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.333 _refine_diff_density_min -0.207 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 3141 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0433 _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^)+(0.0561P)^2^+0.7836P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1008 _refine_ls_wR_factor_ref 0.1102 _reflns_number_gt 2389 _reflns_number_total 3141 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file hk2439.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Cl Cl1 0.55602(2) 0.84379(11) 0.19724(2) 0.03406(16) Uani d . 1 Cl Cl2 0.683870(19) 0.21813(13) 0.05939(3) 0.04287(18) Uani d . 1 O O1 0.45551(5) 0.8154(2) 0.11531(7) 0.0276(3) Uani d . 1 N N1 0.43595(6) 0.3718(3) 0.12891(8) 0.0251(4) Uani d . 1 H H1B 0.4481 0.2049 0.1303 0.030 Uiso calc R 1 C C1 0.38119(6) 0.4124(4) 0.13939(10) 0.0246(4) Uani d . 1 H H1A 0.3743 0.6126 0.1403 0.029 Uiso calc R 1 C C2 0.35016(7) 0.2882(5) 0.08417(9) 0.0309(5) Uani d . 1 H H2A 0.3568 0.0901 0.0821 0.037 Uiso calc R 1 H H2B 0.3607 0.3698 0.0421 0.037 Uiso calc R 1 C C3 0.29284(8) 0.3379(5) 0.09487(10) 0.0375(5) Uani d . 1 H H3A 0.2858 0.5356 0.0927 0.045 Uiso calc R 1 H H3B 0.2731 0.2480 0.0595 0.045 Uiso calc R 1 C C4 0.27550(7) 0.2290(5) 0.16035(10) 0.0333(5) Uani d . 1 H H4A 0.2780 0.0280 0.1602 0.040 Uiso calc R 1 H H4B 0.2392 0.2784 0.1673 0.040 Uiso calc R 1 C C5 0.30768(8) 0.3422(5) 0.21592(10) 0.0382(5) Uani d . 1 H H5A 0.2973 0.2548 0.2575 0.046 Uiso calc R 1 H H5B 0.3014 0.5401 0.2200 0.046 Uiso calc R 1 C C6 0.36460(7) 0.2927(5) 0.20447(9) 0.0317(5) Uani d . 1 H H6A 0.3847 0.3769 0.2403 0.038 Uiso calc R 1 H H6B 0.3715 0.0946 0.2048 0.038 Uiso calc R 1 C C7 0.46841(7) 0.5748(4) 0.11741(8) 0.0193(4) Uani d . 1 C C8 0.52252(6) 0.4894(3) 0.10407(8) 0.0179(4) Uani d . 1 C C9 0.56448(7) 0.6043(4) 0.13615(8) 0.0214(4) Uani d . 1 C C10 0.61389(7) 0.5236(4) 0.12231(9) 0.0256(4) Uani d . 1 H H10A 0.6421 0.6031 0.1447 0.031 Uiso calc R 1 C C11 0.62169(7) 0.3258(4) 0.07559(9) 0.0256(4) Uani d . 1 C C12 0.58138(7) 0.2087(4) 0.04197(9) 0.0247(4) Uani d . 1 H H12A 0.5873 0.0740 0.0096 0.030 Uiso calc R 1 C C13 0.53219(7) 0.2924(4) 0.05662(9) 0.0213(4) Uani d . 1 H H13A 0.5042 0.2134 0.0337 0.026 Uiso calc R 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 Cl1 0.0376(3) 0.0338(3) 0.0307(3) -0.0036(2) -0.0058(2) -0.0119(2) Cl2 0.0182(2) 0.0630(4) 0.0474(3) 0.0106(2) 0.0028(2) 0.0024(3) O1 0.0274(7) 0.0119(7) 0.0436(8) 0.0027(5) 0.0016(6) 0.0005(6) N1 0.0181(8) 0.0111(7) 0.0463(10) 0.0031(6) 0.0046(7) -0.0003(7) C1 0.0170(8) 0.0140(9) 0.0428(11) 0.0028(7) 0.0061(8) 0.0019(8) C2 0.0229(10) 0.0470(13) 0.0229(10) 0.0073(9) 0.0017(8) 0.0067(9) C3 0.0219(10) 0.0570(15) 0.0335(11) 0.0077(10) -0.0015(9) 0.0059(10) C4 0.0191(9) 0.0394(13) 0.0413(12) -0.0002(9) 0.0046(8) 0.0033(10) C5 0.0295(11) 0.0534(15) 0.0318(11) 0.0005(10) 0.0091(9) -0.0050(10) C6 0.0243(10) 0.0472(14) 0.0237(9) -0.0002(9) -0.0003(8) -0.0091(9) C7 0.0220(9) 0.0160(9) 0.0199(8) 0.0007(7) -0.0008(7) -0.0017(7) C8 0.0202(8) 0.0142(8) 0.0195(8) 0.0000(7) 0.0002(7) 0.0041(7) C9 0.0254(9) 0.0178(9) 0.0209(8) -0.0027(7) -0.0007(7) 0.0025(7) C10 0.0207(9) 0.0320(11) 0.0242(9) -0.0058(8) -0.0045(7) 0.0053(8) C11 0.0170(9) 0.0342(11) 0.0256(9) 0.0044(8) 0.0023(7) 0.0070(8) C12 0.0239(9) 0.0269(11) 0.0235(9) 0.0047(8) 0.0016(7) 0.0003(8) C13 0.0190(9) 0.0206(10) 0.0244(9) 0.0006(7) -0.0021(7) -0.0008(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C9 1.7310(19) ? Cl2 C11 1.7419(19) ? O1 C7 1.231(2) ? N1 C7 1.331(2) ? N1 C1 1.461(2) ? N1 H1B 0.8800 ? C1 C2 1.517(3) ? C1 C6 1.519(3) ? C1 H1A 1.0000 ? C2 C3 1.534(3) ? C2 H2A 0.9900 ? C2 H2B 0.9900 ? C3 C4 1.513(3) ? C3 H3A 0.9900 ? C3 H3B 0.9900 ? C4 C5 1.518(3) ? C4 H4A 0.9900 ? C4 H4B 0.9900 ? C5 C6 1.526(3) ? C5 H5A 0.9900 ? C5 H5B 0.9900 ? C6 H6A 0.9900 ? C6 H6B 0.9900 ? C7 C8 1.501(2) y C8 C13 1.394(2) ? C8 C9 1.396(2) ? C9 C10 1.381(3) ? C10 C11 1.378(3) ? C10 H10A 0.9500 ? C11 C12 1.382(3) ? C12 C13 1.383(3) ? C12 H12A 0.9500 ? C13 H13A 0.9500 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C7 N1 C1 123.28(15) C7 N1 H1B 118.4 C1 N1 H1B 118.4 N1 C1 C2 110.95(16) N1 C1 C6 110.96(16) C2 C1 C6 110.05(15) N1 C1 H1A 108.3 C2 C1 H1A 108.3 C6 C1 H1A 108.3 C1 C2 C3 110.49(17) C1 C2 H2A 109.6 C3 C2 H2A 109.6 C1 C2 H2B 109.6 C3 C2 H2B 109.6 H2A C2 H2B 108.1 C4 C3 C2 111.41(16) C4 C3 H3A 109.3 C2 C3 H3A 109.3 C4 C3 H3B 109.3 C2 C3 H3B 109.3 H3A C3 H3B 108.0 C3 C4 C5 111.50(18) C3 C4 H4A 109.3 C5 C4 H4A 109.3 C3 C4 H4B 109.3 C5 C4 H4B 109.3 H4A C4 H4B 108.0 C4 C5 C6 111.40(17) C4 C5 H5A 109.3 C6 C5 H5A 109.3 C4 C5 H5B 109.3 C6 C5 H5B 109.3 H5A C5 H5B 108.0 C1 C6 C5 110.70(17) C1 C6 H6A 109.5 C5 C6 H6A 109.5 C1 C6 H6B 109.5 C5 C6 H6B 109.5 H6A C6 H6B 108.1 O1 C7 N1 123.48(16) O1 C7 C8 121.36(16) N1 C7 C8 115.11(15) C13 C8 C9 117.66(16) C13 C8 C7 119.55(15) C9 C8 C7 122.76(15) C10 C9 C8 121.43(17) C10 C9 Cl1 117.70(14) C8 C9 Cl1 120.82(14) C11 C10 C9 119.00(17) C11 C10 H10A 120.5 C9 C10 H10A 120.5 C10 C11 C12 121.64(17) C10 C11 Cl2 119.08(14) C12 C11 Cl2 119.28(15) C11 C12 C13 118.43(18) C11 C12 H12A 120.8 C13 C12 H12A 120.8 C12 C13 C8 121.83(17) C12 C13 H13A 119.1 C8 C13 H13A 119.1 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 C7 N1 C1 C2 113.7(2) C7 N1 C1 C6 -123.64(19) N1 C1 C2 C3 -178.66(16) C6 C1 C2 C3 58.1(2) C1 C2 C3 C4 -56.3(2) C2 C3 C4 C5 54.1(3) C3 C4 C5 C6 -54.1(3) N1 C1 C6 C5 178.53(16) C2 C1 C6 C5 -58.3(2) C4 C5 C6 C1 56.2(2) C1 N1 C7 O1 0.9(3) C1 N1 C7 C8 -176.58(16) O1 C7 C8 C13 -126.00(18) N1 C7 C8 C13 51.5(2) O1 C7 C8 C9 52.3(2) N1 C7 C8 C9 -130.16(18) C13 C8 C9 C10 -1.0(3) C7 C8 C9 C10 -179.29(16) C13 C8 C9 Cl1 -178.28(13) C7 C8 C9 Cl1 3.4(2) C8 C9 C10 C11 0.2(3) Cl1 C9 C10 C11 177.62(14) C9 C10 C11 C12 0.6(3) C9 C10 C11 Cl2 -178.55(14) C10 C11 C12 C13 -0.7(3) Cl2 C11 C12 C13 178.49(14) C11 C12 C13 C8 -0.1(3) C9 C8 C13 C12 0.9(3) C7 C8 C13 C12 179.29(17) 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 N1 H1B O1 1_545 0.88 1.95 2.796(3) 161.00 yes _cod_database_code 2218142