#------------------------------------------------------------------------------ #$Date: 2012-02-24 19:13:23 +0200 (Fri, 24 Feb 2012) $ #$Revision: 34330 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/50/00/4500000.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_4500000 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 'C24 H18 N2 O7' _chemical_formula_weight 446.40 _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 98.191(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 32.531(5) _cell_length_b 5.2697(8) _cell_length_c 24.159(4) _cell_measurement_temperature 100(2) _cell_volume 4099.3(11) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _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 0.0783 _diffrn_reflns_av_sigmaI/netI 0.1039 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 9531 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.26 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_T_max 0.9978 _exptl_absorpt_correction_T_min 0.9787 _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1856 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.418 _refine_diff_density_min -0.454 _refine_diff_density_rms 0.106 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.284 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 303 _refine_ls_number_reflns 3601 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.284 _refine_ls_R_factor_all 0.1857 _refine_ls_R_factor_gt 0.1556 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0854P)^2^+89.8013P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3480 _refine_ls_wR_factor_ref 0.3607 _reflns_number_gt 2778 _reflns_number_total 3601 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file jm147.cif _[local]_cod_data_source_block jm147 _cod_original_cell_volume 4099.4(11) _cod_database_code 4500000 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 0.3505(2) 0.6064(13) 0.2874(3) 0.0332(17) Uani 1 1 d . . . N2 N 0.3743(2) 0.3828(14) 0.2195(3) 0.0189(16) Uani 1 1 d . . . N1 N 0.4195(3) 0.5891(15) 0.2871(3) 0.0265(19) Uani 1 1 d . . . H1A H 0.4247 0.6853 0.3170 0.032 Uiso 1 1 calc R . . H1B H 0.4401 0.5310 0.2707 0.032 Uiso 1 1 calc R . . C16 C 0.3164(3) 0.4991(18) 0.1484(4) 0.027(2) Uani 1 1 d . . . C11 C 0.3321(3) 0.3447(17) 0.1929(4) 0.024(2) Uani 1 1 d . . . C24 C 0.4075(3) 0.3325(17) 0.1878(4) 0.021(2) Uani 1 1 d . . . C19 C 0.4117(3) 0.483(2) 0.1425(4) 0.028(2) Uani 1 1 d . . . C10 C 0.3804(3) 0.5313(17) 0.2665(4) 0.022(2) Uani 1 1 d . . . C12 C 0.3076(3) 0.162(2) 0.2122(4) 0.031(2) Uani 1 1 d . . . H12A H 0.3196 0.0511 0.2410 0.038 Uiso 1 1 calc R . . C23 C 0.4351(3) 0.141(2) 0.2051(4) 0.031(2) Uani 1 1 d . . . H23A H 0.4304 0.0342 0.2352 0.037 Uiso 1 1 calc R . . C15 C 0.2745(3) 0.468(2) 0.1281(4) 0.035(3) Uani 1 1 d . . . H15A H 0.2626 0.5726 0.0980 0.042 Uiso 1 1 calc R . . C17 C 0.3417(4) 0.684(2) 0.1227(4) 0.035(3) Uani 1 1 d . . . H17A H 0.3270 0.8266 0.1059 0.042 Uiso 1 1 calc R . . C18 C 0.3819(3) 0.6795(19) 0.1196(4) 0.030(2) Uani 1 1 d . . . H18A H 0.3927 0.8170 0.1007 0.036 Uiso 1 1 calc R . . C14 C 0.2499(3) 0.297(2) 0.1487(5) 0.042(3) Uani 1 1 d . . . H14A H 0.2212 0.2862 0.1340 0.050 Uiso 1 1 calc R . . C13 C 0.2668(3) 0.136(2) 0.1917(5) 0.042(3) Uani 1 1 d . . . H13A H 0.2502 0.0106 0.2063 0.051 Uiso 1 1 calc R . . C22 C 0.4700(3) 0.101(2) 0.1789(5) 0.040(3) Uani 1 1 d . . . H22A H 0.4893 -0.0293 0.1913 0.048 Uiso 1 1 calc R . . C20 C 0.4476(3) 0.444(2) 0.1163(4) 0.042(3) Uani 1 1 d . . . H20A H 0.4522 0.5480 0.0857 0.051 Uiso 1 1 calc R . . C21 C 0.4761(3) 0.253(3) 0.1351(5) 0.044(3) Uani 1 1 d . . . H21A H 0.5000 0.2296 0.1171 0.052 Uiso 1 1 calc R . . C8 C 0.4161(3) 1.4411(17) 0.4287(3) 0.020(2) Uani 1 1 d . . . H8A H 0.4412 1.4018 0.4147 0.025 Uiso 1 1 calc R . . C6 C 0.3436(2) 1.3525(16) 0.4323(3) 0.0159(18) Uani 1 1 d . . . H6A H 0.3195 1.2522 0.4217 0.019 Uiso 1 1 calc R . . C7 C 0.3812(3) 1.2967(17) 0.4128(3) 0.0176(19) Uani 1 1 d . . . C1 C 0.4523(3) 1.8011(17) 0.4803(4) 0.0185(19) Uani 1 1 d . . . C4 C 0.3429(3) 1.5615(16) 0.4680(3) 0.0138(17) Uani 1 1 d . . . C3 C 0.3776(2) 1.7068(16) 0.4839(3) 0.0146(18) Uani 1 1 d . . . H3A H 0.3764 1.8495 0.5076 0.018 Uiso 1 1 calc R . . C2 C 0.4149(3) 1.6418(16) 0.4647(3) 0.0163(18) Uani 1 1 d . . . C9 C 0.3848(3) 1.0792(16) 0.3736(3) 0.0177(19) Uani 1 1 d . . . C5 C 0.3026(3) 1.6343(17) 0.4847(4) 0.0200(19) Uani 1 1 d . . . O4 O 0.41775(19) 1.0191(12) 0.3592(3) 0.0243(15) Uani 1 1 d . . . O2 O 0.44930(18) 1.9932(12) 0.5104(3) 0.0232(15) Uani 1 1 d . . . H2A H 0.4725 2.0661 0.5168 0.035 Uiso 0.50 1 calc PR . . O5 O 0.34942(19) 0.9623(12) 0.3582(3) 0.0236(15) Uani 1 1 d . . . H5A H 0.3528 0.8487 0.3349 0.035 Uiso 1 1 calc R . . O3 O 0.48471(18) 1.7346(14) 0.4616(3) 0.0314(17) Uani 1 1 d . . . H3B H 0.5041 1.8350 0.4731 0.047 Uiso 0.50 1 calc PR . . O6 O 0.27263(18) 1.4749(13) 0.4754(3) 0.0278(16) Uani 1 1 d . . . H6B H 0.2506 1.5436 0.4821 0.042 Uiso 1 1 calc R . . O7 O 0.2993(2) 1.8514(12) 0.5065(3) 0.0270(15) Uani 1 1 d . . . O1W O 0.488(3) 0.64(2) 0.262(4) 0.05(4) Uiso 0.07(2) 1 d P . . 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 0.044(4) 0.029(4) 0.028(4) -0.005(3) 0.009(3) 0.009(3) N2 0.022(4) 0.019(4) 0.016(4) -0.005(3) 0.003(3) -0.002(3) N1 0.044(5) 0.018(4) 0.019(4) -0.006(3) 0.009(3) -0.013(4) C16 0.045(6) 0.019(5) 0.017(4) -0.008(4) 0.003(4) 0.014(4) C11 0.032(5) 0.019(5) 0.024(5) -0.011(4) 0.016(4) -0.001(4) C24 0.027(5) 0.014(4) 0.024(5) -0.002(4) 0.008(4) -0.011(4) C19 0.029(5) 0.033(6) 0.022(5) -0.002(4) 0.002(4) -0.006(5) C10 0.036(5) 0.015(4) 0.014(4) 0.006(4) 0.005(4) 0.002(4) C12 0.023(5) 0.037(6) 0.033(5) -0.006(5) 0.000(4) 0.007(5) C23 0.035(6) 0.032(6) 0.026(5) -0.002(4) 0.003(4) 0.003(5) C15 0.032(6) 0.042(7) 0.027(5) -0.007(5) -0.007(4) 0.010(5) C17 0.059(7) 0.023(5) 0.021(5) 0.005(4) -0.008(5) 0.012(5) C18 0.050(7) 0.028(6) 0.010(4) 0.002(4) 0.000(4) -0.009(5) C14 0.021(5) 0.057(8) 0.046(7) -0.020(6) 0.002(5) 0.017(6) C13 0.033(6) 0.050(7) 0.044(7) -0.011(6) 0.008(5) -0.016(6) C22 0.014(5) 0.058(8) 0.046(7) -0.012(6) 0.001(4) -0.004(5) C20 0.051(7) 0.056(8) 0.023(5) -0.020(5) 0.015(5) -0.036(6) C21 0.018(5) 0.071(9) 0.045(7) -0.025(6) 0.014(5) -0.010(6) C8 0.020(5) 0.024(5) 0.018(4) 0.004(4) 0.001(4) 0.007(4) C6 0.014(4) 0.016(4) 0.018(4) 0.006(4) 0.004(3) -0.006(4) C7 0.022(5) 0.017(5) 0.013(4) 0.006(3) 0.000(3) 0.001(4) C1 0.020(5) 0.015(4) 0.020(4) 0.002(4) 0.001(4) 0.000(4) C4 0.023(4) 0.016(4) 0.003(3) 0.006(3) 0.002(3) 0.005(4) C3 0.025(5) 0.010(4) 0.009(4) 0.001(3) 0.003(3) 0.003(4) C2 0.019(4) 0.013(4) 0.017(4) 0.007(3) 0.005(3) -0.006(4) C9 0.023(5) 0.016(4) 0.015(4) 0.005(4) 0.004(3) 0.002(4) C5 0.022(5) 0.014(5) 0.024(5) 0.005(4) 0.002(4) -0.005(4) O4 0.022(3) 0.020(3) 0.033(4) -0.005(3) 0.013(3) -0.004(3) O2 0.018(3) 0.024(4) 0.026(3) -0.006(3) -0.002(3) 0.001(3) O5 0.028(3) 0.019(3) 0.024(3) -0.012(3) 0.003(3) -0.004(3) O3 0.009(3) 0.044(4) 0.043(4) -0.006(4) 0.007(3) 0.002(3) O6 0.013(3) 0.031(4) 0.041(4) -0.012(3) 0.010(3) -0.011(3) O7 0.033(4) 0.023(4) 0.029(4) -0.003(3) 0.019(3) -0.002(3) 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 C10 N2 C24 121.1(7) . . ? C10 N2 C11 117.7(7) . . ? C24 N2 C11 118.4(7) . . ? C11 C16 C15 115.9(10) . . ? C11 C16 C17 123.5(9) . . ? C15 C16 C17 120.6(9) . . ? C12 C11 C16 120.5(9) . . ? C12 C11 N2 120.5(9) . . ? C16 C11 N2 119.0(8) . . ? C19 C24 C23 122.0(9) . . ? C19 C24 N2 119.1(8) . . ? C23 C24 N2 118.8(8) . . ? C24 C19 C20 116.9(10) . . ? C24 C19 C18 124.9(9) . . ? C20 C19 C18 118.2(9) . . ? O1 C10 N1 123.0(9) . . ? O1 C10 N2 119.8(9) . . ? N1 C10 N2 117.2(8) . . ? C13 C12 C11 122.3(10) . . ? C24 C23 C22 120.7(10) . . ? C14 C15 C16 123.7(10) . . ? C18 C17 C16 129.1(9) . . ? C17 C18 C19 126.4(9) . . ? C15 C14 C13 119.3(10) . . ? C12 C13 C14 118.2(11) . . ? C21 C22 C23 118.9(11) . . ? C21 C20 C19 120.7(10) . . ? C22 C21 C20 120.6(10) . . ? C2 C8 C7 120.3(8) . . ? C7 C6 C4 117.6(8) . . ? C8 C7 C6 121.1(8) . . ? C8 C7 C9 117.4(8) . . ? C6 C7 C9 121.5(8) . . ? O3 C1 O2 124.8(8) . . ? O3 C1 C2 116.8(8) . . ? O2 C1 C2 118.3(8) . . ? C3 C4 C6 121.8(8) . . ? C3 C4 C5 120.3(7) . . ? C6 C4 C5 117.7(8) . . ? C4 C3 C2 119.1(8) . . ? C8 C2 C3 120.1(8) . . ? C8 C2 C1 120.1(8) . . ? C3 C2 C1 119.7(8) . . ? O4 C9 O5 124.7(8) . . ? O4 C9 C7 122.1(8) . . ? O5 C9 C7 113.1(7) . . ? O7 C5 O6 123.8(8) . . ? O7 C5 C4 118.5(8) . . ? O6 C5 C4 117.7(8) . . ? 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 C10 1.224(11) . ? N2 C10 1.370(11) . ? N2 C24 1.434(11) . ? N2 C11 1.445(12) . ? N1 C10 1.333(12) . ? C16 C11 1.386(13) . ? C16 C15 1.391(14) . ? C16 C17 1.467(15) . ? C11 C12 1.373(14) . ? C24 C19 1.372(13) . ? C24 C23 1.378(13) . ? C19 C20 1.420(14) . ? C19 C18 1.471(14) . ? C12 C13 1.355(14) . ? C23 C22 1.390(14) . ? C15 C14 1.347(16) . ? C17 C18 1.323(14) . ? C14 C13 1.394(16) . ? C22 C21 1.365(17) . ? C20 C21 1.398(17) . ? C8 C2 1.374(12) . ? C8 C7 1.378(12) . ? C6 C7 1.400(12) . ? C6 C4 1.401(12) . ? C7 C9 1.502(12) . ? C1 O3 1.255(10) . ? C1 O2 1.258(10) . ? C1 C2 1.481(12) . ? C4 C3 1.373(12) . ? C4 C5 1.477(12) . ? C3 C2 1.402(11) . ? C9 O4 1.216(10) . ? C9 O5 1.312(10) . ? C5 O7 1.271(11) . ? C5 O6 1.282(10) . ? O1W O1W 1.05(19) 2_655 ?