#------------------------------------------------------------------------------ #$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2015296.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_2015296 loop_ _publ_author_name 'Harrison, William T. A.' 'Yathirajan, H. S.' 'Anilkumar, H. G.' _publ_section_title ; An orthorhombic polymorph of 10,11-dihydrocarbamazepine ; _journal_coeditor_code FG3005 _journal_issue 5 _journal_name_full 'Acta Crystallographica, Section C' _journal_page_first o240 _journal_page_last o242 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C15 H14 N2 O' _chemical_formula_moiety 'C15 H14 N2 O' _chemical_formula_sum 'C15 H14 N2 O' _chemical_formula_weight 238.28 _chemical_name_common ; 10,11-dihydrocarbamazepine ; _chemical_name_systematic ; 10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide ; _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens 'difmap (N-H) and geom (C-H)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 9.0592(4) _cell_length_b 10.3156(5) _cell_length_c 25.0534(12) _cell_measurement_reflns_used 3022 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.91 _cell_volume 2341.27(19) _computing_cell_refinement 'HKL SCALEPACK (Otwinowski & Minor 1997)' _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_data_reduction ; HKL DENZO (Otwinowski & Minor 1997), SCALEPACK and SORTAV (Blessing 1995) ; _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '\w and \f' _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 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 16158 _diffrn_reflns_theta_full 27.58 _diffrn_reflns_theta_max 27.58 _diffrn_reflns_theta_min 3.10 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_correction_T_min 0.976 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1008 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.236 _refine_diff_density_min -0.203 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 169 _refine_ls_number_reflns 2680 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.085 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0416 _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^)+(0.0384P)^2^+1.5004P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1041 _refine_ls_wR_factor_ref 0.1084 _reflns_number_gt 2289 _reflns_number_total 2680 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fg3005.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' 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_ _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 0.04963(15) 0.45082(13) 0.37391(5) 0.0177(3) Uani d . 1 C C2 0.14657(15) 0.54877(14) 0.38949(5) 0.0200(3) Uani d . 1 H H2A 0.1536 0.5714 0.4262 0.024 Uiso calc R 1 C C3 0.23264(16) 0.61353(14) 0.35245(6) 0.0228(3) Uani d . 1 H H3 0.3000 0.6787 0.3636 0.027 Uiso calc R 1 C C4 0.21937(17) 0.58193(15) 0.29865(6) 0.0253(3) Uani d . 1 H H4 0.2769 0.6262 0.2727 0.030 Uiso calc R 1 C C5 0.12199(16) 0.48575(15) 0.28318(6) 0.0234(3) Uani d . 1 H H5 0.1129 0.4661 0.2463 0.028 Uiso calc R 1 C C6 0.03620(15) 0.41617(13) 0.31986(5) 0.0188(3) Uani d . 1 C C7 -0.06149(16) 0.30985(14) 0.29711(5) 0.0208(3) Uani d . 1 H H7A 0.0013 0.2524 0.2751 0.025 Uiso calc R 1 H H7B -0.1339 0.3510 0.2729 0.025 Uiso calc R 1 C C8 -0.14691(16) 0.22474(14) 0.33658(5) 0.0207(3) Uani d . 1 H H8A -0.2016 0.1570 0.3167 0.025 Uiso calc R 1 H H8B -0.0766 0.1811 0.3609 0.025 Uiso calc R 1 C C9 -0.25370(16) 0.30443(13) 0.36874(5) 0.0184(3) Uani d . 1 C C10 -0.40531(16) 0.30161(14) 0.36045(5) 0.0212(3) Uani d . 1 H H10 -0.4457 0.2440 0.3347 0.025 Uiso calc R 1 C C11 -0.49873(16) 0.38233(14) 0.38948(5) 0.0220(3) Uani d . 1 H H11 -0.6023 0.3794 0.3836 0.026 Uiso calc R 1 C C12 -0.44072(16) 0.46712(13) 0.42704(5) 0.0212(3) Uani d . 1 H H12 -0.5047 0.5224 0.4466 0.025 Uiso calc R 1 C C13 -0.28875(16) 0.47151(13) 0.43614(5) 0.0197(3) Uani d . 1 H H13 -0.2487 0.5293 0.4618 0.024 Uiso calc R 1 C C14 -0.19696(15) 0.38982(13) 0.40696(5) 0.0172(3) Uani d . 1 C C15 0.02724(16) 0.32816(13) 0.45697(5) 0.0182(3) Uani d . 1 N N1 -0.03947(12) 0.39139(11) 0.41466(4) 0.0181(3) Uani d . 1 N N2 -0.06459(15) 0.27514(13) 0.49331(5) 0.0228(3) Uani d . 1 H H1 -0.0204(19) 0.2325(18) 0.5196(7) 0.027 Uiso d . 1 H H2 -0.165(2) 0.2717(17) 0.4898(7) 0.027 Uiso d . 1 O O1 0.16274(11) 0.32075(10) 0.46096(4) 0.0238(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 0.0158(7) 0.0189(6) 0.0186(6) 0.0031(5) 0.0004(5) 0.0026(5) C2 0.0180(7) 0.0211(7) 0.0210(6) 0.0029(5) -0.0015(5) -0.0005(5) C3 0.0187(7) 0.0214(7) 0.0283(7) -0.0003(6) -0.0011(6) 0.0027(5) C4 0.0217(8) 0.0286(8) 0.0255(7) -0.0020(6) 0.0021(6) 0.0075(6) C5 0.0230(7) 0.0289(7) 0.0181(6) 0.0022(6) 0.0015(5) 0.0029(5) C6 0.0172(7) 0.0204(6) 0.0189(6) 0.0031(5) 0.0004(5) 0.0021(5) C7 0.0208(7) 0.0248(7) 0.0168(6) 0.0008(6) 0.0008(5) -0.0007(5) C8 0.0227(7) 0.0188(7) 0.0207(6) -0.0006(5) -0.0002(5) -0.0013(5) C9 0.0195(7) 0.0184(6) 0.0174(6) -0.0008(5) -0.0001(5) 0.0037(5) C10 0.0216(7) 0.0224(7) 0.0196(6) -0.0036(6) -0.0021(5) 0.0028(5) C11 0.0165(7) 0.0244(7) 0.0251(7) -0.0007(6) -0.0010(5) 0.0080(6) C12 0.0214(7) 0.0212(7) 0.0209(6) 0.0039(5) 0.0034(5) 0.0042(5) C13 0.0220(7) 0.0196(6) 0.0175(6) 0.0001(5) 0.0000(5) 0.0017(5) C14 0.0166(7) 0.0188(6) 0.0163(6) 0.0003(5) -0.0003(5) 0.0041(5) C15 0.0208(7) 0.0187(6) 0.0152(6) 0.0014(5) -0.0010(5) -0.0016(5) N1 0.0156(6) 0.0234(6) 0.0153(5) 0.0002(5) -0.0001(4) 0.0023(4) N2 0.0203(6) 0.0288(7) 0.0192(6) 0.0010(5) -0.0009(5) 0.0065(5) O1 0.0181(5) 0.0315(6) 0.0219(5) 0.0017(4) -0.0021(4) 0.0045(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.3945(19) C1 C6 1.4057(18) C1 N1 1.4387(17) C2 C3 1.3841(19) C2 H2A 0.9500 C3 C4 1.392(2) C3 H3 0.9500 C4 C5 1.383(2) C4 H4 0.9500 C5 C6 1.4013(19) C5 H5 0.9500 C6 C7 1.5201(19) C7 C8 1.5321(19) C7 H7A 0.9900 C7 H7B 0.9900 C8 C9 1.5036(19) C8 H8A 0.9900 C8 H8B 0.9900 C9 C10 1.389(2) C9 C14 1.3989(18) C10 C11 1.392(2) C10 H10 0.9500 C11 C12 1.388(2) C11 H11 0.9500 C12 C13 1.396(2) C12 H12 0.9500 C13 C14 1.3914(19) C13 H13 0.9500 C14 N1 1.4398(17) C15 O1 1.2339(17) C15 N2 1.3492(18) C15 N1 1.3836(16) N2 H1 0.887(18) N2 H2 0.915(18) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 C1 C6 120.56(12) C2 C1 N1 117.60(12) C6 C1 N1 121.79(12) C3 C2 C1 121.11(13) C3 C2 H2A 119.4 C1 C2 H2A 119.4 C2 C3 C4 119.19(14) C2 C3 H3 120.4 C4 C3 H3 120.4 C5 C4 C3 119.63(13) C5 C4 H4 120.2 C3 C4 H4 120.2 C4 C5 C6 122.51(13) C4 C5 H5 118.7 C6 C5 H5 118.7 C5 C6 C1 116.97(13) C5 C6 C7 116.53(12) C1 C6 C7 126.50(12) C6 C7 C8 117.75(11) C6 C7 H7A 107.9 C8 C7 H7A 107.9 C6 C7 H7B 107.9 C8 C7 H7B 107.9 H7A C7 H7B 107.2 C9 C8 C7 110.94(11) C9 C8 H8A 109.5 C7 C8 H8A 109.5 C9 C8 H8B 109.5 C7 C8 H8B 109.5 H8A C8 H8B 108.0 C10 C9 C14 118.60(13) C10 C9 C8 122.99(12) C14 C9 C8 118.34(12) C9 C10 C11 120.68(13) C9 C10 H10 119.7 C11 C10 H10 119.7 C12 C11 C10 120.06(13) C12 C11 H11 120.0 C10 C11 H11 120.0 C11 C12 C13 120.29(13) C11 C12 H12 119.9 C13 C12 H12 119.9 C14 C13 C12 118.95(13) C14 C13 H13 120.5 C12 C13 H13 120.5 C13 C14 C9 121.42(13) C13 C14 N1 120.99(12) C9 C14 N1 117.58(12) O1 C15 N2 122.25(12) O1 C15 N1 121.72(12) N2 C15 N1 116.03(12) C15 N1 C1 119.97(11) C15 N1 C14 122.02(11) C1 N1 C14 117.75(10) C15 N2 H1 115.0(11) C15 N2 H2 124.3(11) H1 N2 H2 120.1(16) 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 C6 C1 C2 C3 -0.5(2) ? N1 C1 C2 C3 -177.94(12) ? C1 C2 C3 C4 1.4(2) ? C2 C3 C4 C5 -0.7(2) ? C3 C4 C5 C6 -1.0(2) ? C4 C5 C6 C1 1.8(2) ? C4 C5 C6 C7 -177.74(13) ? C2 C1 C6 C5 -1.08(19) ? N1 C1 C6 C5 176.22(12) ? C2 C1 C6 C7 178.44(13) ? N1 C1 C6 C7 -4.2(2) y C5 C6 C7 C8 175.09(12) ? C1 C6 C7 C8 -4.4(2) y C6 C7 C8 C9 62.06(16) y C7 C8 C9 C10 106.33(15) ? C7 C8 C9 C14 -70.51(15) y C14 C9 C10 C11 0.17(19) ? C8 C9 C10 C11 -176.66(12) ? C9 C10 C11 C12 0.2(2) ? C10 C11 C12 C13 -0.3(2) ? C11 C12 C13 C14 0.1(2) ? C12 C13 C14 C9 0.34(19) ? C12 C13 C14 N1 179.59(12) ? C10 C9 C14 C13 -0.45(19) ? C8 C9 C14 C13 176.52(12) ? C10 C9 C14 N1 -179.73(11) ? C8 C9 C14 N1 -2.76(17) y O1 C15 N1 C1 -0.1(2) ? N2 C15 N1 C1 -179.94(12) ? O1 C15 N1 C14 173.90(13) ? N2 C15 N1 C14 -5.95(19) ? C2 C1 N1 C15 -60.38(17) ? C6 C1 N1 C15 122.24(14) ? C2 C1 N1 C14 125.37(13) ? C6 C1 N1 C14 -52.01(17) y C13 C14 N1 C15 79.78(17) ? C9 C14 N1 C15 -100.94(15) ? C13 C14 N1 C1 -106.10(14) ? C9 C14 N1 C1 73.18(16) y 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 N2 H1 Cg1 4_556 0.887(18) 2.86 3.75 173 N2 H2 O1 4_456 0.915(18) 2.206(18) 2.8970(16) 131.7(14) _cod_database_code 2015296