#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/31/2013198.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_2013198 loop_ _publ_author_name 'Bowes, Katharine F.' 'Glidewell, Christopher' 'Low, John N.' 'Skakle, Janet M. S.' 'Wardell, James L.' _publ_section_title ; A triclinic polymorph of benzanilide: disordered molecules form hydrogen-bonded chains ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o1 _journal_page_last o3 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C13 H11 N O' _chemical_formula_sum 'C13 H11 N O' _chemical_formula_weight 197.23 _chemical_name_common Benzanilide _chemical_name_systematic ; N-phenylbenzamide (triclinic polymorph) ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 72.702(3) _cell_angle_beta 79.389(3) _cell_angle_gamma 89.914(5) _cell_formula_units_Z 2 _cell_length_a 5.3406(5) _cell_length_b 7.7727(7) _cell_length_c 12.3901(15) _cell_measurement_reflns_used 2140 _cell_measurement_temperature 120.00(10) _cell_measurement_theta_max 27.51 _cell_measurement_theta_min 3.51 _cell_volume 481.89(9) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD Server Software (Nonius, 1997)' _computing_data_reduction DENZO-SMN _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120.00(10) _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.969 _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.079 _diffrn_reflns_av_sigmaI/netI 0.111 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 7033 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 27.51 _diffrn_reflns_theta_min 3.51 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_correction_T_min 0.989 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO-SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 208 _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.27 _refine_diff_density_min -0.25 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 159 _refine_ls_number_reflns 2140 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 0.959 _refine_ls_R_factor_all 0.149 _refine_ls_R_factor_gt 0.061 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0761P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.130 _refine_ls_wR_factor_ref 0.160 _reflns_number_gt 1092 _reflns_number_total 2140 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1598.cif _[local]_cod_data_source_block I _cod_database_code 2013198 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 O11 -0.1228(5) 0.7445(8) 0.0032(3) 0.0310(9) Uani d P 0.839(5) A 1 O C11 0.3558(7) 0.7580(4) -0.1536(2) 0.0205(7) Uani d P 0.839(5) A 1 C C12 0.1972(7) 0.8436(5) -0.2274(3) 0.0218(8) Uani d P 0.839(5) A 1 C C13 0.2568(10) 0.8509(8) -0.3418(3) 0.0265(9) Uani d P 0.839(5) A 1 C C14 0.4726(13) 0.7742(11) -0.3849(4) 0.0287(10) Uani d P 0.839(5) A 1 C C15 0.6307(9) 0.6894(8) -0.3111(4) 0.0274(9) Uani d P 0.839(5) A 1 C C16 0.5744(6) 0.6806(4) -0.1961(3) 0.0240(8) Uani d P 0.839(5) A 1 C C17 0.0825(5) 0.7454(4) 0.0341(3) 0.0233(7) Uani d P 0.839(5) A 1 C N11 0.3126(4) 0.7517(3) -0.0365(2) 0.0236(6) Uani d P 0.839(5) A 1 N C21 0.0876(7) 0.7398(4) 0.1551(2) 0.0237(8) Uani d P 0.839(5) A 1 C C22 -0.1161(6) 0.6534(5) 0.2412(3) 0.0257(8) Uani d P 0.839(5) A 1 C C23 -0.1225(10) 0.6464(10) 0.3541(4) 0.0277(9) Uani d P 0.839(5) A 1 C C24 0.0742(16) 0.7284(14) 0.3831(4) 0.0305(10) Uani d P 0.839(5) A 1 C C25 0.2777(11) 0.8169(9) 0.2974(4) 0.0318(11) Uani d P 0.839(5) A 1 C C26 0.2871(7) 0.8208(5) 0.1846(3) 0.0261(9) Uani d P 0.839(5) A 1 C N31 0.2751(7) 0.7473(5) 0.0386(3) 0.049(4) Uiso d PRD 0.161(5) A 2 N C37 0.129(3) 0.753(3) -0.0384(11) 0.041(4) Uiso d PD 0.161(5) A 2 C O31 -0.108(3) 0.744(5) -0.022(3) 0.041(4) Uiso d PD 0.161(5) A 2 O C31 0.187(3) 0.737(3) 0.1560(8) 0.026(4) Uiso d PGD 0.161(5) A 2 C C32 -0.038(3) 0.649(3) 0.2266(17) 0.026(4) Uiso d PG 0.161(5) A 2 C C33 -0.094(5) 0.645(5) 0.3413(17) 0.026(4) Uiso d PG 0.161(5) A 2 C C34 0.074(7) 0.730(6) 0.3855(14) 0.026(4) Uiso d PG 0.161(5) A 2 C C35 0.299(6) 0.817(5) 0.3149(19) 0.026(4) Uiso d PG 0.161(5) A 2 C C36 0.355(3) 0.821(3) 0.2001(16) 0.026(4) Uiso d PG 0.161(5) A 2 C C41 0.254(3) 0.761(3) -0.1574(13) 0.036(4) Uiso d PGD 0.161(5) A 2 C C42 0.135(4) 0.852(3) -0.247(2) 0.036(4) Uiso d PG 0.161(5) A 2 C C43 0.246(6) 0.864(5) -0.3602(17) 0.036(4) Uiso d PG 0.161(5) A 2 C C44 0.475(7) 0.784(6) -0.3831(15) 0.036(4) Uiso d PG 0.161(5) A 2 C C45 0.594(5) 0.693(5) -0.293(2) 0.036(4) Uiso d PG 0.161(5) A 2 C C46 0.483(3) 0.681(3) -0.1803(18) 0.036(4) Uiso d PG 0.161(5) A 2 C H12 0.0488 0.8969 -0.1994 0.026 Uiso calc PR 0.839(5) A 1 H H13 0.1478 0.9096 -0.3923 0.032 Uiso calc PR 0.839(5) A 1 H H14 0.5109 0.7800 -0.4639 0.034 Uiso calc PR 0.839(5) A 1 H H15 0.7791 0.6366 -0.3396 0.033 Uiso calc PR 0.839(5) A 1 H H16 0.6840 0.6221 -0.1458 0.029 Uiso calc PR 0.839(5) A 1 H H11 0.4488 0.7518 -0.0059 0.028 Uiso calc PR 0.839(5) A 1 H H22 -0.2533 0.5982 0.2221 0.031 Uiso calc PR 0.839(5) A 1 H H23 -0.2623 0.5850 0.4123 0.033 Uiso calc PR 0.839(5) A 1 H H24 0.0699 0.7241 0.4608 0.037 Uiso calc PR 0.839(5) A 1 H H25 0.4118 0.8753 0.3165 0.038 Uiso calc PR 0.839(5) A 1 H H26 0.4297 0.8788 0.1269 0.031 Uiso calc PR 0.839(5) A 1 H H31 0.4412 0.7501 0.0146 0.059 Uiso calc PR 0.161(5) A 2 H H32 -0.1528 0.5913 0.1964 0.031 Uiso calc PR 0.161(5) A 2 H H33 -0.2479 0.5853 0.3896 0.031 Uiso calc PR 0.161(5) A 2 H H34 0.0354 0.7272 0.4639 0.031 Uiso calc PR 0.161(5) A 2 H H35 0.4138 0.8750 0.3451 0.031 Uiso calc PR 0.161(5) A 2 H H36 0.5088 0.8809 0.1519 0.031 Uiso calc PR 0.161(5) A 2 H H42 -0.0215 0.9059 -0.2317 0.044 Uiso calc PR 0.161(5) A 2 H H43 0.1652 0.9259 -0.4217 0.044 Uiso calc PR 0.161(5) A 2 H H44 0.5511 0.7926 -0.4602 0.044 Uiso calc PR 0.161(5) A 2 H H45 0.7504 0.6392 -0.3088 0.044 Uiso calc PR 0.161(5) A 2 H H46 0.5637 0.6191 -0.1188 0.044 Uiso calc PR 0.161(5) A 2 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 O11 0.0221(13) 0.0532(15) 0.021(2) 0.0018(10) -0.0043(10) -0.0152(18) C11 0.0197(16) 0.0194(15) 0.0212(17) -0.0035(14) -0.0025(12) -0.0054(12) C12 0.0187(16) 0.0250(16) 0.025(2) 0.0027(13) -0.0078(14) -0.0097(15) C13 0.0266(17) 0.0258(19) 0.026(2) -0.0021(13) -0.0098(17) -0.0039(17) C14 0.0342(18) 0.027(2) 0.0248(18) -0.0052(14) -0.0004(13) -0.0114(13) C15 0.0263(19) 0.0255(17) 0.031(2) 0.0004(15) -0.0001(15) -0.0127(17) C16 0.0217(17) 0.0210(15) 0.028(2) 0.0014(14) -0.0065(14) -0.0046(13) C17 0.0206(15) 0.0218(14) 0.0262(18) 0.0005(11) -0.0018(12) -0.0069(13) N11 0.0166(12) 0.0306(14) 0.0234(15) 0.0005(10) -0.0053(10) -0.0070(11) C21 0.0216(16) 0.0278(17) 0.0229(19) 0.0056(16) -0.0051(14) -0.0091(13) C22 0.0181(17) 0.0275(17) 0.033(2) 0.0048(16) -0.0058(15) -0.0108(14) C23 0.0251(19) 0.0312(18) 0.025(2) 0.0043(15) -0.0003(13) -0.0080(16) C24 0.0377(19) 0.0330(19) 0.0221(18) 0.0098(14) -0.0079(13) -0.0089(13) C25 0.034(2) 0.0312(18) 0.036(3) 0.0015(15) -0.0141(19) -0.014(2) C26 0.0212(17) 0.0257(17) 0.0298(19) 0.0006(16) -0.0050(14) -0.0059(14) 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 O11 C17 . 1.227(4) no C11 C12 . 1.385(4) no C11 C16 . 1.400(4) no C11 N11 . 1.412(4) no C12 C13 . 1.379(4) no C12 H12 . 0.95 no C13 C14 . 1.389(4) no C13 H13 . 0.95 no C14 C15 . 1.381(5) no C14 H14 . 0.95 no C15 C16 . 1.382(5) no C15 H15 . 0.95 no C16 H16 . 0.95 no C17 N11 . 1.362(3) no C17 C21 . 1.491(4) no N11 H11 . 0.88 no C21 C22 . 1.386(4) no C21 C26 . 1.396(4) no C22 C23 . 1.378(5) no C22 H22 . 0.95 no C23 C24 . 1.384(5) no C23 H23 . 0.95 no C24 C25 . 1.388(4) no C24 H24 . 0.95 no C25 C26 . 1.380(4) no C25 H25 . 0.95 no C26 H26 . 0.95 no N31 C37 . 1.331(9) no N31 C31 . 1.422(9) no N31 H31 . 0.88 no C37 O31 . 1.241(10) no C37 C41 . 1.487(10) no C31 C32 . 1.39 no C31 C36 . 1.39 no C32 C33 . 1.39 no C32 H32 . 0.95 no C33 C34 . 1.39 no C33 H33 . 0.95 no C34 C35 . 1.39 no C34 H34 . 0.95 no C35 C36 . 1.39 no C35 H35 . 0.95 no C36 H36 . 0.95 no C41 C42 . 1.39 no C41 C46 . 1.39 no C42 C43 . 1.39 no C42 H42 . 0.95 no C43 C44 . 1.39 no C43 H43 . 0.95 no C44 C45 . 1.39 no C44 H44 . 0.95 no C45 C46 . 1.39 no C45 H45 . 0.95 no C46 H46 . 0.95 no 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' 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 C12 C11 C16 119.7(3) no C12 C11 N11 122.5(3) no C16 C11 N11 117.8(3) no C13 C12 C11 119.3(3) no C13 C12 H12 120.3 no C11 C12 H12 120.3 no C12 C13 C14 121.5(3) no C12 C13 H13 119.3 no C14 C13 H13 119.3 no C15 C14 C13 119.0(3) no C15 C14 H14 120.5 no C13 C14 H14 120.5 no C14 C15 C16 120.4(3) no C14 C15 H15 119.8 no C16 C15 H15 119.8 no C15 C16 C11 120.1(3) no C15 C16 H16 120.0 no C11 C16 H16 120.0 no O11 C17 N11 123.6(3) no O11 C17 C21 119.7(3) no N11 C17 C21 116.7(3) no C17 N11 C11 126.9(2) no C17 N11 H11 116.5 no C11 N11 H11 116.5 no C22 C21 C26 118.8(3) no C22 C21 C17 118.6(3) no C26 C21 C17 122.6(3) no C23 C22 C21 121.0(3) no C23 C22 H22 119.5 no C21 C22 H22 119.5 no C22 C23 C24 120.2(3) no C22 C23 H23 119.9 no C24 C23 H23 119.9 no C23 C24 C25 119.3(3) no C23 C24 H24 120.3 no C25 C24 H24 120.3 no C26 C25 C24 120.6(3) no C26 C25 H25 119.7 no C24 C25 H25 119.7 no C25 C26 C21 120.1(3) no C25 C26 H26 119.9 no C21 C26 H26 119.9 no C37 N31 C31 125.7(9) no C37 N31 H31 117.1 no C31 N31 H31 117.1 no O31 C37 N31 127.7(18) no O31 C37 C41 113.7(17) no N31 C37 C41 118.5(14) no C32 C31 C36 120.0 no C32 C31 N31 126.7(13) no C36 C31 N31 113.3(13) no C31 C32 C33 120.0 no C31 C32 H32 120.0 no C33 C32 H32 120.0 no C32 C33 C34 120.0 no C32 C33 H33 120.0 no C34 C33 H33 120.0 no C33 C34 C35 120.0 no C33 C34 H34 120.0 no C35 C34 H34 120.0 no C36 C35 C34 120.0 no C36 C35 H35 120.0 no C34 C35 H35 120.0 no C35 C36 C31 120.0 no C35 C36 H36 120.0 no C31 C36 H36 120.0 no C42 C41 C46 120.0 no C42 C41 C37 117.9(17) no C46 C41 C37 122.1(17) no C41 C42 C43 120.0 no C41 C42 H42 120.0 no C43 C42 H42 120.0 no C42 C43 C44 120.0 no C42 C43 H43 120.0 no C44 C43 H43 120.0 no C43 C44 C45 120.0 no C43 C44 H44 120.0 no C45 C44 H44 120.0 no C46 C45 C44 120.0 no C46 C45 H45 120.0 no C44 C45 H45 120.0 no C45 C46 C41 120.0 no C45 C46 H46 120.0 no C41 C46 H46 120.0 no 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 N11 H11 O11 1_655 0.88 2.31 3.141(4) 157 y N11 H11 O31 1_655 0.88 2.34 3.13(2) 150 y N31 H31 O11 1_655 0.88 2.31 3.17(3) 165 y N31 H31 O31 1_655 0.88 2.37 3.24(3) 172 y 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 C11 N11 C17 C21 -179.8(3) y C12 C11 N11 C17 32.5(5) y N11 C17 C21 C22 -150.7(3) y _cod_database_fobs_code 2013198