#------------------------------------------------------------------------------ #$Date: 2014-07-12 05:32:21 +0300 (Sat, 12 Jul 2014) $ #$Revision: 120110 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/50/00/4500011.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_4500011 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_volume 3 _journal_year 2003 _chemical_formula_sum 'C38 H30 N4 O4' _chemical_formula_weight 606.66 _chemical_name_systematic ; ? ; _space_group_IT_number 15 _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 92.105(8) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 29.191(16) _cell_length_b 4.962(3) _cell_length_c 20.316(11) _cell_measurement_temperature 200(2) _cell_volume 2941(3) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 200(2) _diffrn_measured_fraction_theta_full 0.885 _diffrn_measured_fraction_theta_max 0.885 _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 0.0510 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 3831 _diffrn_reflns_theta_full 21.83 _diffrn_reflns_theta_max 21.83 _diffrn_reflns_theta_min 1.40 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_T_max 0.9910 _exptl_absorpt_correction_T_min 0.9822 _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.166 _refine_diff_density_min -0.132 _refine_diff_density_rms 0.038 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 1559 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.026 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0351 _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^)+(0.0535P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0898 _refine_ls_wR_factor_ref 0.0931 _reflns_number_gt 1301 _reflns_number_total 1559 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file sf6212a.cif _[local]_cod_data_source_block sf6212a _cod_database_code 4500011 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_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 0.45036(5) 1.0681(3) 0.30402(7) 0.0366(5) Uani 1 1 d . . . O2 O 0.42295(5) 1.0622(3) 0.04427(7) 0.0379(5) Uani 1 1 d . . . N1 N 0.44867(6) 1.0825(3) 0.19253(8) 0.0335(5) Uani 1 1 d . . . H1A H 0.4765 1.1505 0.1919 0.040 Uiso 1 1 calc R . . H1B H 0.4332 1.0510 0.1554 0.040 Uiso 1 1 calc R . . N2 N 0.38565(6) 0.9257(3) 0.24815(7) 0.0267(5) Uani 1 1 d . . . C1 C 0.42972(8) 1.0267(4) 0.25069(11) 0.0276(6) Uani 1 1 d . . . C2 C 0.36036(7) 0.8605(4) 0.18839(9) 0.0237(5) Uani 1 1 d . . . C3 C 0.37529(7) 0.6516(4) 0.14873(9) 0.0280(6) Uani 1 1 d . . . H3A H 0.4012 0.5473 0.1626 0.034 Uiso 1 1 calc R . . C4 C 0.35282(8) 0.5952(4) 0.08976(10) 0.0305(6) Uani 1 1 d . . . H4A H 0.3632 0.4531 0.0628 0.037 Uiso 1 1 calc R . . C5 C 0.31506(8) 0.7464(4) 0.06996(10) 0.0324(6) Uani 1 1 d . . . H5A H 0.2998 0.7108 0.0288 0.039 Uiso 1 1 calc R . . C6 C 0.29940(8) 0.9499(4) 0.11004(9) 0.0301(6) Uani 1 1 d . . . H6A H 0.2732 1.0517 0.0961 0.036 Uiso 1 1 calc R . . C7 C 0.32138(8) 1.0084(4) 0.17074(10) 0.0243(6) Uani 1 1 d . . . C8 C 0.30224(7) 1.2155(4) 0.21326(9) 0.0283(6) Uani 1 1 d . . . H8A H 0.2870 1.3619 0.1917 0.034 Uiso 1 1 calc R . . C9 C 0.30388(7) 1.2207(4) 0.27933(9) 0.0288(6) Uani 1 1 d . . . H9A H 0.2897 1.3708 0.2992 0.035 Uiso 1 1 calc R . . C10 C 0.32493(7) 1.0226(4) 0.32424(9) 0.0255(6) Uani 1 1 d . . . C11 C 0.30551(8) 0.9741(4) 0.38524(10) 0.0309(6) Uani 1 1 d . . . H11A H 0.2800 1.0784 0.3979 0.037 Uiso 1 1 calc R . . C12 C 0.32282(8) 0.7774(4) 0.42727(10) 0.0329(6) Uani 1 1 d . . . H12A H 0.3095 0.7495 0.4687 0.039 Uiso 1 1 calc R . . C13 C 0.35951(8) 0.6209(4) 0.40945(9) 0.0323(6) Uani 1 1 d . . . H13A H 0.3708 0.4822 0.4379 0.039 Uiso 1 1 calc R . . C14 C 0.37973(8) 0.6675(4) 0.34988(9) 0.0303(6) Uani 1 1 d . . . H14A H 0.4049 0.5601 0.3373 0.036 Uiso 1 1 calc R . . C15 C 0.36326(7) 0.8710(4) 0.30854(9) 0.0243(5) Uani 1 1 d . . . C16 C 0.43592(8) 0.9371(4) -0.00318(11) 0.0328(6) Uani 1 1 d . . . H16A H 0.4238 0.9889 -0.0454 0.039 Uiso 1 1 calc R . . C17 C 0.46878(7) 0.7122(4) -0.00033(9) 0.0258(6) Uani 1 1 d . . . C18 C 0.48819(8) 0.6191(4) 0.05905(10) 0.0303(6) Uani 1 1 d . . . H18A H 0.4802 0.7008 0.0993 0.036 Uiso 1 1 calc R . . C19 C 0.51910(7) 0.4074(4) 0.05932(10) 0.0293(6) Uani 1 1 d . . . H19A H 0.5321 0.3433 0.0999 0.035 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 0.0291(9) 0.0525(11) 0.0278(9) -0.0072(7) -0.0032(8) -0.0058(8) O2 0.0392(10) 0.0341(9) 0.0408(10) -0.0011(8) 0.0046(8) 0.0031(8) N1 0.0267(11) 0.0455(13) 0.0282(10) -0.0005(9) 0.0008(9) -0.0077(10) N2 0.0223(12) 0.0345(11) 0.0234(10) -0.0025(8) -0.0002(9) -0.0009(10) C1 0.0264(15) 0.0297(13) 0.0266(14) -0.0036(10) 0.0006(13) 0.0047(12) C2 0.0232(13) 0.0279(12) 0.0200(11) -0.0001(10) 0.0004(11) -0.0035(12) C3 0.0280(14) 0.0283(13) 0.0279(12) 0.0044(10) 0.0033(11) 0.0005(12) C4 0.0368(15) 0.0295(14) 0.0253(13) -0.0021(10) 0.0047(12) -0.0057(13) C5 0.0348(15) 0.0382(15) 0.0240(12) 0.0011(11) -0.0021(12) -0.0080(14) C6 0.0276(14) 0.0328(14) 0.0299(13) 0.0053(11) -0.0005(12) -0.0004(12) C7 0.0257(14) 0.0232(12) 0.0241(12) 0.0036(10) 0.0009(11) -0.0040(12) C8 0.0286(14) 0.0237(13) 0.0327(13) 0.0046(10) 0.0017(11) 0.0016(12) C9 0.0293(14) 0.0237(13) 0.0336(13) -0.0018(10) 0.0048(11) 0.0011(11) C10 0.0271(14) 0.0241(12) 0.0254(12) -0.0037(10) 0.0004(11) -0.0027(12) C11 0.0278(14) 0.0348(14) 0.0303(13) -0.0036(11) 0.0031(12) 0.0011(12) C12 0.0322(15) 0.0390(15) 0.0279(12) -0.0013(12) 0.0054(12) -0.0059(14) C13 0.0397(16) 0.0306(14) 0.0262(12) 0.0020(10) -0.0057(12) -0.0062(14) C14 0.0292(14) 0.0329(13) 0.0283(12) -0.0048(11) -0.0032(11) 0.0040(12) C15 0.0224(13) 0.0300(13) 0.0203(12) -0.0025(10) -0.0020(11) -0.0051(12) C16 0.0319(15) 0.0305(14) 0.0358(14) 0.0019(12) -0.0009(12) -0.0064(13) C17 0.0234(13) 0.0245(13) 0.0294(13) 0.0015(10) 0.0003(11) -0.0024(12) C18 0.0328(14) 0.0303(13) 0.0278(12) -0.0020(10) 0.0014(11) -0.0038(13) C19 0.0290(15) 0.0284(13) 0.0302(13) 0.0053(10) -0.0031(11) -0.0044(13) 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 C1 N2 C2 124.31(16) . . ? C1 N2 C15 119.30(17) . . ? C2 N2 C15 116.36(17) . . ? O1 C1 N1 122.0(2) . . ? O1 C1 N2 121.09(18) . . ? N1 C1 N2 116.9(2) . . ? C7 C2 C3 120.9(2) . . ? C7 C2 N2 119.37(18) . . ? C3 C2 N2 119.7(2) . . ? C4 C3 C2 120.5(2) . . ? C3 C4 C5 119.6(2) . . ? C4 C5 C6 120.1(2) . . ? C5 C6 C7 121.2(2) . . ? C2 C7 C6 117.55(18) . . ? C2 C7 C8 122.96(19) . . ? C6 C7 C8 119.5(2) . . ? C9 C8 C7 127.1(2) . . ? C8 C9 C10 127.61(19) . . ? C15 C10 C11 117.6(2) . . ? C15 C10 C9 122.85(18) . . ? C11 C10 C9 119.5(2) . . ? C12 C11 C10 121.1(2) . . ? C11 C12 C13 120.3(2) . . ? C12 C13 C14 119.6(2) . . ? C13 C14 C15 120.1(2) . . ? C14 C15 C10 121.12(19) . . ? C14 C15 N2 119.73(19) . . ? C10 C15 N2 119.15(19) . . ? O2 C16 C17 125.2(2) . . ? C18 C17 C19 119.68(19) . 5_665 ? C18 C17 C16 121.98(18) . . ? C19 C17 C16 118.3(2) 5_665 . ? C19 C18 C17 119.97(18) . . ? C18 C19 C17 120.35(19) . 5_665 ? 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 C1 1.237(2) . ? O2 C16 1.218(2) . ? N1 C1 1.352(2) . ? N2 C1 1.380(3) . ? N2 C2 1.434(3) . ? N2 C15 1.437(2) . ? C2 C7 1.390(3) . ? C2 C3 1.393(3) . ? C3 C4 1.373(3) . ? C4 C5 1.381(3) . ? C5 C6 1.385(3) . ? C6 C7 1.400(3) . ? C7 C8 1.466(3) . ? C8 C9 1.342(3) . ? C9 C10 1.462(3) . ? C10 C15 1.395(3) . ? C10 C11 1.402(3) . ? C11 C12 1.380(3) . ? C12 C13 1.382(3) . ? C13 C14 1.385(3) . ? C14 C15 1.388(3) . ? C16 C17 1.471(3) . ? C17 C18 1.393(3) . ? C17 C19 1.395(3) 5_665 ? C18 C19 1.385(3) . ? C19 C17 1.395(3) 5_665 ? 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 C2 N2 C1 O1 -176.92(18) . . . . ? C15 N2 C1 O1 0.7(3) . . . . ? C2 N2 C1 N1 4.4(3) . . . . ? C15 N2 C1 N1 -177.99(17) . . . . ? C1 N2 C2 C7 -114.2(2) . . . . ? C15 N2 C2 C7 68.1(2) . . . . ? C1 N2 C2 C3 65.4(3) . . . . ? C15 N2 C2 C3 -112.3(2) . . . . ? C7 C2 C3 C4 2.9(3) . . . . ? N2 C2 C3 C4 -176.74(17) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C3 C4 C5 C6 -1.4(3) . . . . ? C4 C5 C6 C7 0.5(3) . . . . ? C3 C2 C7 C6 -3.7(3) . . . . ? N2 C2 C7 C6 175.97(17) . . . . ? C3 C2 C7 C8 174.99(18) . . . . ? N2 C2 C7 C8 -5.4(3) . . . . ? C5 C6 C7 C2 2.0(3) . . . . ? C5 C6 C7 C8 -176.70(17) . . . . ? C2 C7 C8 C9 -30.9(3) . . . . ? C6 C7 C8 C9 147.7(2) . . . . ? C7 C8 C9 C10 -0.1(4) . . . . ? C8 C9 C10 C15 30.9(3) . . . . ? C8 C9 C10 C11 -147.2(2) . . . . ? C15 C10 C11 C12 -2.0(3) . . . . ? C9 C10 C11 C12 176.17(19) . . . . ? C10 C11 C12 C13 -0.9(3) . . . . ? C11 C12 C13 C14 1.8(3) . . . . ? C12 C13 C14 C15 0.2(3) . . . . ? C13 C14 C15 C10 -3.3(3) . . . . ? C13 C14 C15 N2 177.33(19) . . . . ? C11 C10 C15 C14 4.1(3) . . . . ? C9 C10 C15 C14 -174.03(19) . . . . ? C11 C10 C15 N2 -176.49(18) . . . . ? C9 C10 C15 N2 5.4(3) . . . . ? C1 N2 C15 C14 -66.4(3) . . . . ? C2 N2 C15 C14 111.4(2) . . . . ? C1 N2 C15 C10 114.2(2) . . . . ? C2 N2 C15 C10 -68.0(2) . . . . ? O2 C16 C17 C18 0.5(3) . . . . ? O2 C16 C17 C19 -178.8(2) . . . 5_665 ? C19 C17 C18 C19 -0.5(3) 5_665 . . . ? C16 C17 C18 C19 -179.77(18) . . . . ? C17 C18 C19 C17 0.5(3) . . . 5_665 ? _journal_paper_doi 10.1021/cg034035x