############################################################################## ### ### ### Electronic paper (Acta Crystallographica Section E) ### ### ### ############################################################################## # # # This CIF contains the data in a paper accepted for publication in Acta # # Crystallographica Section E. It conforms to the requirements of Notes # # for Authors for Section E, and has been peer reviewed under the auspices # # of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4. # # # # Software is freely available for graphical display of the structure(s) in # # this CIF. For information consult the CIF home page http://www.iucr.org/ # # cif/home.html # # # # This file may be used for bona fide research purposes within the # # scientific community so long as proper attribution is given to the journal # # article from which it was obtained. # # # ############################################################################## data_I _audit_creation_method 'WinGX routine CIF_UPDATE' _chemical_name_systematic ; N-(4-Chlorophenyl)-benzamide ; _chemical_formula_moiety 'C13 H10 Cl N O' _chemical_formula_sum 'C13 H10 Cl N O' _chemical_formula_iupac 'C13 H10 Cl N O' _chemical_formula_weight 231.67 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.37890(10) _cell_length_b 7.8501(2) _cell_length_c 13.6318(4) _cell_angle_alpha 106.509(2) _cell_angle_beta 98.380(2) _cell_angle_gamma 90.631(2) _cell_volume 545.15(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 13860 _cell_measurement_theta_min 3.1396 _cell_measurement_theta_max 29.3009 _cell_measurement_temperature 295(2) _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 240 _exptl_absorpt_coefficient_mu 0.325 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; [CrysAlis RED (Oxford Diffraction, 2007). Analytical absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)] ; _exptl_absorpt_correction_T_min 0.852 _exptl_absorpt_correction_T_max 0.975 _exptl_special_details ; ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur' _diffrn_measurement_device '4-circle kappa geometry goniometer' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_detector_area_resol_mean 10.434 _diffrn_reflns_number 23656 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_theta_min 5.62 _diffrn_reflns_theta_max 25.84 _diffrn_reflns_theta_full 25.84 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measured_fraction_theta_full 0.988 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > \s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2087 _reflns_number_gt 1773 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0381 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_gt 0.0886 _refine_ls_wR_factor_ref 0.0912 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.078 _refine_ls_number_reflns 2087 _refine_ls_number_parameters 148 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0494P)^2^+0.0939P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.187 _refine_diff_density_min -0.226 _refine_ls_extinction_method none 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' _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2007)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2007)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2007)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002) ; _computing_publication_material ; SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and WinGX (Farrugia, 1999) ; 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 _atom_site_disorder_assembly _atom_site_disorder_group N N1 0.3126(2) 0.77177(16) 0.02982(9) 0.0381(3) Uani d D 1 . . H H1N 0.443(3) 0.757(2) 0.0010(13) 0.046 Uiso d D 1 . . O O1 -0.11350(19) 0.74813(17) 0.00041(8) 0.0563(3) Uani d . 1 . . C C1 0.0870(2) 0.71549(18) -0.03078(10) 0.0370(3) Uani d . 1 . . C C2 0.0976(2) 0.61312(17) -0.14032(10) 0.0343(3) Uani d . 1 . . C C3 -0.1018(2) 0.62387(19) -0.21496(11) 0.0396(3) Uani d . 1 . . H H3 -0.2346 0.6941 -0.1956 0.047 Uiso calc R 1 . . C C4 -0.1045(3) 0.5314(2) -0.31747(11) 0.0450(3) Uani d . 1 . . H H4 -0.2376 0.5409 -0.3671 0.054 Uiso calc R 1 . . C C5 0.0893(3) 0.4249(2) -0.34662(11) 0.0460(4) Uani d . 1 . . H H5 0.0871 0.3621 -0.4158 0.055 Uiso calc R 1 . . C C6 0.2867(3) 0.41171(19) -0.27281(12) 0.0452(3) Uani d . 1 . . H H6 0.4167 0.3387 -0.2924 0.054 Uiso calc R 1 . . C C7 0.2930(3) 0.50593(18) -0.17026(11) 0.0392(3) Uani d . 1 . . H H7 0.4281 0.4977 -0.1211 0.047 Uiso calc R 1 . . C C8 0.3531(2) 0.87653(17) 0.13439(10) 0.0337(3) Uani d . 1 . . C C9 0.1943(3) 0.86476(19) 0.20396(10) 0.0396(3) Uani d . 1 . . H H9 0.0509 0.7884 0.1818 0.048 Uiso calc R 1 . . C C10 0.2490(3) 0.96646(19) 0.30619(11) 0.0415(3) Uani d . 1 . . H H10 0.1426 0.9588 0.353 0.05 Uiso calc R 1 . . C C11 0.4617(3) 1.07920(18) 0.33843(10) 0.0396(3) Uani d . 1 . . C C12 0.6211(3) 1.09201(19) 0.27047(11) 0.0419(3) Uani d . 1 . . H H12 0.7643 1.1685 0.293 0.05 Uiso calc R 1 . . C C13 0.56679(8) 0.99040(5) 0.16848(3) 0.0391(3) Uani d . 1 . . H H13 0.6744 0.9983 0.1222 0.047 Uiso calc R 1 . . Cl Cl1 0.53006(8) 1.20876(5) 0.46690(3) 0.06227(17) 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 N1 0.0320(6) 0.0455(7) 0.0326(6) 0.0003(5) 0.0068(5) 0.0037(5) O1 0.0336(5) 0.0849(8) 0.0394(6) 0.0060(5) 0.0073(4) -0.0005(5) C1 0.0337(7) 0.0404(7) 0.0347(7) 0.0024(5) 0.0045(5) 0.0076(6) C2 0.0328(7) 0.0340(7) 0.0345(7) -0.0022(5) 0.0060(5) 0.0069(5) C3 0.0328(7) 0.0422(7) 0.0400(7) 0.0032(5) 0.0043(5) 0.0066(6) C4 0.0402(8) 0.0505(8) 0.0379(7) -0.0029(6) -0.0035(6) 0.0075(6) C5 0.0487(8) 0.0474(8) 0.0342(7) -0.0054(6) 0.0074(6) -0.0009(6) C6 0.0394(8) 0.0436(8) 0.0471(8) 0.0043(6) 0.0117(6) 0.0020(6) C7 0.0335(7) 0.0412(7) 0.0394(7) 0.0023(5) 0.0026(5) 0.0077(6) C8 0.0325(6) 0.0343(7) 0.0323(6) 0.0043(5) 0.0039(5) 0.0067(5) C9 0.0343(7) 0.0451(8) 0.0369(7) -0.0042(6) 0.0026(5) 0.0097(6) C10 0.0404(7) 0.0510(8) 0.0333(7) 0.0031(6) 0.0084(6) 0.0113(6) C11 0.0442(8) 0.0378(7) 0.0317(7) 0.0065(6) 0.0004(6) 0.0043(5) C12 0.0369(7) 0.0385(7) 0.0441(8) -0.0035(6) 0.0005(6) 0.0051(6) C13 0.0347(7) 0.0416(7) 0.0401(7) 0.0007(5) 0.0091(6) 0.0089(6) Cl1 0.0764(3) 0.0615(3) 0.0352(2) -0.0009(2) -0.00138(18) -0.00280(18) _geom_special_details ; All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. ; 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 N1 C1 . 1.3560(18) ? N1 C8 . 1.4125(17) ? N1 H1N . 0.845(16) ? O1 C1 . 1.2196(16) ? C1 C2 . 1.4909(18) ? C2 C3 . 1.3876(19) ? C2 C7 . 1.3885(19) ? C3 C4 . 1.377(2) ? C3 H3 . 0.93 ? C4 C5 . 1.376(2) ? C4 H4 . 0.93 ? C5 C6 . 1.379(2) ? C5 H5 . 0.93 ? C6 C7 . 1.379(2) ? C6 H6 . 0.93 ? C7 H7 . 0.93 ? C8 C13 . 1.3862(13) ? C8 C9 . 1.3862(18) ? C9 C10 . 1.3817(19) ? C9 H9 . 0.93 ? C10 C11 . 1.377(2) ? C10 H10 . 0.93 ? C11 C12 . 1.373(2) ? C11 Cl1 . 1.7402(14) ? C12 C13 . 1.3786(15) ? C12 H12 . 0.93 ? C13 H13 . 0.93 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C8 . . 126.64(11) ? C1 N1 H1N . . 117.7(11) ? C8 N1 H1N . . 115.0(12) ? O1 C1 N1 . . 123.02(12) ? O1 C1 C2 . . 121.31(12) ? N1 C1 C2 . . 115.66(11) ? C3 C2 C7 . . 119.04(12) ? C3 C2 C1 . . 117.62(11) ? C7 C2 C1 . . 123.33(12) ? C4 C3 C2 . . 120.51(12) ? C4 C3 H3 . . 119.7 ? C2 C3 H3 . . 119.7 ? C5 C4 C3 . . 120.17(13) ? C5 C4 H4 . . 119.9 ? C3 C4 H4 . . 119.9 ? C4 C5 C6 . . 119.71(13) ? C4 C5 H5 . . 120.1 ? C6 C5 H5 . . 120.1 ? C7 C6 C5 . . 120.53(13) ? C7 C6 H6 . . 119.7 ? C5 C6 H6 . . 119.7 ? C6 C7 C2 . . 120.02(13) ? C6 C7 H7 . . 120 ? C2 C7 H7 . . 120 ? C13 C8 C9 . . 119.42(11) ? C13 C8 N1 . . 117.74(10) ? C9 C8 N1 . . 122.80(12) ? C10 C9 C8 . . 120.05(12) ? C10 C9 H9 . . 120 ? C8 C9 H9 . . 120 ? C11 C10 C9 . . 119.65(12) ? C11 C10 H10 . . 120.2 ? C9 C10 H10 . . 120.2 ? C12 C11 C10 . . 120.97(13) ? C12 C11 Cl1 . . 119.21(11) ? C10 C11 Cl1 . . 119.82(11) ? C11 C12 C13 . . 119.40(12) ? C11 C12 H12 . . 120.3 ? C13 C12 H12 . . 120.3 ? C12 C13 C8 . . 120.52(9) ? C12 C13 H13 . . 119.7 ? C8 C13 H13 . . 119.7 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C8 N1 C1 O1 . . . . -1.4(2) ? C8 N1 C1 C2 . . . . 177.27(12) ? O1 C1 C2 C3 . . . . 28.33(19) ? N1 C1 C2 C3 . . . . -150.35(12) ? O1 C1 C2 C7 . . . . -150.27(14) ? N1 C1 C2 C7 . . . . 31.06(18) ? C7 C2 C3 C4 . . . . -0.8(2) ? C1 C2 C3 C4 . . . . -179.47(12) ? C2 C3 C4 C5 . . . . 1.0(2) ? C3 C4 C5 C6 . . . . -0.3(2) ? C4 C5 C6 C7 . . . . -0.7(2) ? C5 C6 C7 C2 . . . . 1.0(2) ? C3 C2 C7 C6 . . . . -0.2(2) ? C1 C2 C7 C6 . . . . 178.39(12) ? C1 N1 C8 C13 . . . . -149.06(12) ? C1 N1 C8 C9 . . . . 33.4(2) ? C13 C8 C9 C10 . . . . 0.24(18) ? N1 C8 C9 C10 . . . . 177.75(12) ? C8 C9 C10 C11 . . . . 0.0(2) ? C9 C10 C11 C12 . . . . -0.1(2) ? C9 C10 C11 Cl1 . . . . 179.53(10) ? C10 C11 C12 C13 . . . . 0.0(2) ? Cl1 C11 C12 C13 . . . . -179.61(9) ? C11 C12 C13 C8 . . . . 0.18(17) ? C9 C8 C13 C12 . . . . -0.32(15) ? N1 C8 C13 C12 . . . . -177.95(10) ? 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 C9 H9 O1 . 0.93 2.43 2.9090(17) 111.9 N1 H1N O1 1_655 0.845(16) 2.390(16) 3.1710(15) 154.0(15) C13 H13 O1 1_655 0.93 2.58 3.2507(11) 129.3 data_global _journal_date_recd_electronic 2008-03-20 _journal_date_accepted 2008-03-26 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2008 _journal_volume 64 _journal_issue 4 _journal_page_first o769 _journal_page_last o769 _journal_paper_category QO _journal_coeditor_code DN2327 _publ_contact_author_name 'Professor B. Thimme Gowda' _publ_contact_author_address ; Department of Chemistry Mangalore University Mangalagangotri 574 199 Mangalore India ; _publ_contact_author_email gowdabt@yahoo.com _publ_contact_author_fax '91 824 2287367' _publ_contact_author_phone '91 824 2287262' _publ_section_title ; N-(4-Chlorophenyl)benzamide ; loop_ _publ_author_name _publ_author_address 'B. Thimme Gowda' ; Department of Chemistry Mangalore University Mangalagangotri 574 199 Mangalore India ; 'Miroslav Tokar\