#------------------------------------------------------------------------------ #$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201982 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/50/00/4500003.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4500003 loop_ _publ_author_name 'Scott G. Fleischman' 'Srinivasan S. Kuduva' 'Jennifer A. McMahon' 'Brian Moulton' 'Rosa D. Bailey Walsh' 'Na\'ir Rodr\'iguez-Hornedo' 'Michael J. Zaworotko' _publ_section_title ; Crystal Engineering of the Composition of Pharmaceutical Phases: Multiple-Component Crystalline Solids Involving Carbamazepine ; _journal_issue 6 _journal_name_full 'Crystal Growth & Design' _journal_page_first 909 _journal_page_last 919 _journal_paper_doi 10.1021/cg034035x _journal_volume 3 _journal_year 2003 _chemical_formula_sum 'C18 H18 N2 O2' _chemical_formula_weight 294.34 _chemical_name_systematic ; ? ; _space_group_IT_number 2 _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 95.809(3) _cell_angle_beta 93.401(4) _cell_angle_gamma 101.362(3) _cell_formula_units_Z 2 _cell_length_a 7.3985(15) _cell_length_b 8.9054(18) _cell_length_c 11.873(2) _cell_measurement_temperature 100(2) _cell_volume 760.5(3) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.912 _diffrn_measured_fraction_theta_max 0.912 _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 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0749 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 3283 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.73 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_T_max 0.9916 _exptl_absorpt_correction_T_min 0.9750 _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.494 _refine_diff_density_min -0.662 _refine_diff_density_rms 0.104 _refine_ls_extinction_coef 0.017(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.665 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 202 _refine_ls_number_reflns 2449 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.665 _refine_ls_R_factor_all 0.1104 _refine_ls_R_factor_gt 0.0768 _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2089 _refine_ls_wR_factor_ref 0.2669 _reflns_number_gt 1824 _reflns_number_total 2449 _reflns_threshold_expression >2sigma(I) _cod_data_source_file jm431.cif _cod_data_source_block jm431 _cod_database_code 4500003 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.0407(3) 0.1193(3) 0.3890(2) 0.0265(7) Uani 1 1 d . . . N1 N 0.8308(3) 0.0601(3) 0.2349(3) 0.0237(8) Uani 1 1 d . . . N2 N 0.8327(3) -0.1076(3) 0.3743(3) 0.0277(8) Uani 1 1 d . . . H2A H 0.8796 -0.1349 0.4372 0.033 Uiso 1 1 calc R . . H2B H 0.7371 -0.1690 0.3350 0.033 Uiso 1 1 calc R . . C1 C 0.8785(4) 0.2176(4) 0.2085(3) 0.0231(9) Uani 1 1 d . . . C14 C 0.6704(4) -0.0352(4) 0.1748(3) 0.0214(9) Uani 1 1 d . . . C9 C 0.4934(4) -0.0051(4) 0.1885(3) 0.0249(9) Uani 1 1 d . . . C10 C 0.3407(4) -0.1057(4) 0.1299(3) 0.0265(9) Uani 1 1 d . . . H10 H 0.2201 -0.0883 0.1411 0.032 Uiso 1 1 calc R . . C13 C 0.6908(4) -0.1617(4) 0.0989(3) 0.0269(9) Uani 1 1 d . . . H13 H 0.8106 -0.1813 0.0882 0.032 Uiso 1 1 calc R . . C7 C 0.5788(4) 0.2698(4) 0.2791(3) 0.0254(9) Uani 1 1 d . . . H7 H 0.5378 0.3466 0.3267 0.031 Uiso 1 1 calc R . . C15 C 0.9076(4) 0.0286(4) 0.3383(3) 0.0215(8) Uani 1 1 d . . . C8 C 0.4657(4) 0.1311(4) 0.2616(3) 0.0238(9) Uani 1 1 d . . . H8 H 0.3559 0.1191 0.3004 0.029 Uiso 1 1 calc R . . C2 C 1.0426(4) 0.2668(4) 0.1597(3) 0.0270(9) Uani 1 1 d . . . H2 H 1.1199 0.1960 0.1407 0.032 Uiso 1 1 calc R . . C5 C 0.8144(4) 0.4717(4) 0.2124(3) 0.0279(9) Uani 1 1 d . . . H5 H 0.7376 0.5430 0.2309 0.033 Uiso 1 1 calc R . . C12 C 0.5381(4) -0.2571(4) 0.0402(3) 0.0268(9) Uani 1 1 d . . . H12 H 0.5531 -0.3419 -0.0112 0.032 Uiso 1 1 calc R . . C11 C 0.3613(4) -0.2300(4) 0.0557(3) 0.0264(9) Uani 1 1 d . . . H11 H 0.2560 -0.2965 0.0156 0.032 Uiso 1 1 calc R . . C3 C 1.0936(4) 0.4186(4) 0.1388(3) 0.0303(10) Uani 1 1 d . . . H3 H 1.2067 0.4525 0.1062 0.036 Uiso 1 1 calc R . . C4 C 0.9802(4) 0.5213(4) 0.1651(3) 0.0273(9) Uani 1 1 d . . . H4 H 1.0156 0.6257 0.1509 0.033 Uiso 1 1 calc R . . C6 C 0.7591(4) 0.3178(4) 0.2333(3) 0.0251(9) Uani 1 1 d . . . O2 O 0.5080(3) 0.3620(3) 0.6474(2) 0.0364(8) Uani 1 1 d . . . C17 C 0.6498(4) 0.3588(5) 0.6012(3) 0.0310(10) Uani 1 1 d . . . C18 C 0.7655(5) 0.5014(5) 0.5648(4) 0.0407(11) Uani 1 1 d . . . H18A H 0.7113 0.5906 0.5876 0.061 Uiso 1 1 calc R . . H18B H 0.7692 0.4889 0.4820 0.061 Uiso 1 1 calc R . . H18C H 0.8914 0.5176 0.6010 0.061 Uiso 1 1 calc R . . C16 C 0.7151(6) 0.2119(6) 0.5767(4) 0.0473(12) Uani 1 1 d . . . H16A H 0.8224 0.2117 0.6291 0.071 Uiso 1 1 calc R . . H16B H 0.7502 0.2025 0.4983 0.071 Uiso 1 1 calc R . . H16C H 0.6156 0.1247 0.5864 0.071 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0131(11) 0.0341(15) 0.0308(15) 0.0127(12) -0.0041(10) -0.0014(10) N1 0.0132(13) 0.0279(17) 0.0310(18) 0.0139(14) -0.0028(11) 0.0029(11) N2 0.0175(14) 0.0309(17) 0.0327(18) 0.0157(15) -0.0086(12) -0.0028(11) C1 0.0148(15) 0.029(2) 0.0248(19) 0.0107(16) -0.0067(13) 0.0010(13) C14 0.0150(15) 0.0229(18) 0.028(2) 0.0130(16) -0.0016(13) 0.0033(13) C9 0.0174(16) 0.030(2) 0.029(2) 0.0160(17) 0.0007(14) 0.0044(14) C10 0.0130(15) 0.031(2) 0.036(2) 0.0155(18) -0.0007(14) 0.0019(14) C13 0.0158(16) 0.033(2) 0.035(2) 0.0166(18) 0.0015(14) 0.0066(14) C7 0.0178(16) 0.033(2) 0.028(2) 0.0085(17) 0.0015(14) 0.0089(15) C15 0.0105(15) 0.029(2) 0.027(2) 0.0100(16) 0.0013(13) 0.0058(13) C8 0.0145(15) 0.031(2) 0.027(2) 0.0084(16) 0.0023(13) 0.0055(14) C2 0.0136(16) 0.034(2) 0.036(2) 0.0133(18) -0.0026(14) 0.0070(14) C5 0.0166(16) 0.032(2) 0.037(2) 0.0122(18) -0.0018(15) 0.0072(14) C12 0.0269(18) 0.0263(19) 0.028(2) 0.0074(17) 0.0003(15) 0.0048(14) C11 0.0198(16) 0.0264(19) 0.031(2) 0.0120(17) -0.0054(14) -0.0013(14) C3 0.0143(16) 0.041(2) 0.038(2) 0.0198(19) 0.0021(15) 0.0034(15) C4 0.0199(17) 0.029(2) 0.033(2) 0.0130(17) -0.0032(15) 0.0012(14) C6 0.0142(16) 0.032(2) 0.030(2) 0.0120(17) -0.0022(14) 0.0031(14) O2 0.0196(13) 0.0351(16) 0.0544(19) 0.0060(14) 0.0080(12) 0.0035(11) C17 0.0149(16) 0.045(2) 0.033(2) 0.0082(19) -0.0047(15) 0.0063(15) C18 0.0172(17) 0.058(3) 0.047(3) 0.017(2) 0.0047(16) 0.0019(17) C16 0.050(2) 0.060(3) 0.044(3) 0.019(2) 0.011(2) 0.031(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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 N1 C14 123.1(2) . . ? C15 N1 C1 116.8(3) . . ? C14 N1 C1 116.9(2) . . ? C2 C1 C6 121.1(3) . . ? C2 C1 N1 119.4(3) . . ? C6 C1 N1 119.4(3) . . ? C9 C14 C13 119.5(3) . . ? C9 C14 N1 121.6(3) . . ? C13 C14 N1 118.9(3) . . ? C10 C9 C14 118.9(3) . . ? C10 C9 C8 119.5(3) . . ? C14 C9 C8 121.6(3) . . ? C11 C10 C9 121.3(3) . . ? C12 C13 C14 120.4(3) . . ? C8 C7 C6 127.8(3) . . ? O1 C15 N2 123.3(3) . . ? O1 C15 N1 120.1(3) . . ? N2 C15 N1 116.5(3) . . ? C7 C8 C9 126.8(3) . . ? C3 C2 C1 120.0(3) . . ? C4 C5 C6 120.8(3) . . ? C13 C12 C11 120.4(4) . . ? C10 C11 C12 119.5(3) . . ? C2 C3 C4 120.1(3) . . ? C3 C4 C5 120.0(3) . . ? C1 C6 C5 117.9(3) . . ? C1 C6 C7 123.4(3) . . ? C5 C6 C7 118.7(3) . . ? O2 C17 C16 121.2(3) . . ? O2 C17 C18 121.8(3) . . ? C16 C17 C18 117.0(3) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C15 1.225(4) . ? N1 C15 1.399(4) . ? N1 C14 1.421(4) . ? N1 C1 1.448(4) . ? N2 C15 1.353(4) . ? C1 C2 1.388(4) . ? C1 C6 1.397(5) . ? C14 C9 1.403(4) . ? C14 C13 1.407(5) . ? C9 C10 1.395(5) . ? C9 C8 1.474(5) . ? C10 C11 1.382(6) . ? C13 C12 1.376(5) . ? C7 C8 1.338(5) . ? C7 C6 1.473(4) . ? C2 C3 1.382(5) . ? C5 C4 1.391(4) . ? C5 C6 1.402(5) . ? C12 C11 1.395(5) . ? C3 C4 1.384(5) . ? O2 C17 1.216(4) . ? C17 C16 1.489(6) . ? C17 C18 1.503(5) . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N1 C1 C2 83.7(4) . . . . ? C14 N1 C1 C2 -115.6(3) . . . . ? C15 N1 C1 C6 -95.9(3) . . . . ? C14 N1 C1 C6 64.8(5) . . . . ? C15 N1 C14 C9 94.0(4) . . . . ? C1 N1 C14 C9 -65.3(4) . . . . ? C15 N1 C14 C13 -86.6(4) . . . . ? C1 N1 C14 C13 114.0(3) . . . . ? C13 C14 C9 C10 2.6(4) . . . . ? N1 C14 C9 C10 -178.0(3) . . . . ? C13 C14 C9 C8 -176.3(3) . . . . ? N1 C14 C9 C8 3.1(4) . . . . ? C14 C9 C10 C11 -2.5(5) . . . . ? C8 C9 C10 C11 176.4(3) . . . . ? C9 C14 C13 C12 -1.3(4) . . . . ? N1 C14 C13 C12 179.4(3) . . . . ? C14 N1 C15 O1 -176.3(3) . . . . ? C1 N1 C15 O1 -17.0(4) . . . . ? C14 N1 C15 N2 6.6(5) . . . . ? C1 N1 C15 N2 165.9(3) . . . . ? C6 C7 C8 C9 -2.3(5) . . . . ? C10 C9 C8 C7 -145.3(3) . . . . ? C14 C9 C8 C7 33.6(5) . . . . ? C6 C1 C2 C3 2.5(5) . . . . ? N1 C1 C2 C3 -177.1(3) . . . . ? C14 C13 C12 C11 -0.4(5) . . . . ? C9 C10 C11 C12 0.9(5) . . . . ? C13 C12 C11 C10 0.6(5) . . . . ? C1 C2 C3 C4 -0.8(6) . . . . ? C2 C3 C4 C5 -0.2(6) . . . . ? C6 C5 C4 C3 -0.5(5) . . . . ? C2 C1 C6 C5 -3.1(5) . . . . ? N1 C1 C6 C5 176.5(3) . . . . ? C2 C1 C6 C7 176.5(3) . . . . ? N1 C1 C6 C7 -3.9(5) . . . . ? C4 C5 C6 C1 2.1(5) . . . . ? C4 C5 C6 C7 -177.5(3) . . . . ? C8 C7 C6 C1 -30.4(5) . . . . ? C8 C7 C6 C5 149.1(4) . . . . ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30661265