#------------------------------------------------------------------------------ #$Date: 2016-03-24 03:23:26 +0200 (Thu, 24 Mar 2016) $ #$Revision: 179628 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/50/92/4509220.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided the Crystal Eye server at # http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the # Peter Murray-Rust laboratory. # # 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_4509220 loop_ _publ_author_name 'Childs, Scott L.' 'Wood, Peter A.' 'Rodr\'iguez-Hornedo, Na\'ir' 'Reddy, L. Sreenivas' 'Hardcastle, Kenneth I.' _publ_contact_author 'Scott L Childs' _publ_section_title ; Analysis of 50 Crystal Structures Containing Carbamazepine Using theMaterialsModule ofMercury CSD ; _journal_issue 4 _journal_name_full 'Crystal Growth & Design' _journal_page_first 1869 _journal_paper_doi 10.1021/cg801056c _journal_volume 9 _journal_year 2009 _chemical_formula_moiety 'C15 H12 N2 O' _chemical_formula_sum 'C15 H12 N2 O' _chemical_formula_weight 236.27 _chemical_name_common 'carbamazepine host structure with DL-tartaric acid removed' _chemical_name_systematic ; 5H-Dibenz(b,f)azepine-5-carboxamide DL-tartaric acid ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/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 104.235(6) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.3006(9) _cell_length_b 26.972(2) _cell_length_c 5.0718(4) _cell_measurement_reflns_used 1868 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 65.88 _cell_measurement_theta_min 3.28 _cell_volume 1365.82(19) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.745 _diffrn_measured_fraction_theta_max 0.745 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0148 _diffrn_reflns_av_sigmaI/netI 0.0158 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_number 3603 _diffrn_reflns_theta_full 65.92 _diffrn_reflns_theta_max 65.92 _diffrn_reflns_theta_min 3.28 _exptl_absorpt_coefficient_mu 0.588 _exptl_absorpt_correction_T_max 0.9656 _exptl_absorpt_correction_T_min 0.9119 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.149 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rod _exptl_crystal_F_000 496 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _platon_squeeze_details ; ; _refine_diff_density_max 0.167 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 1757 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0460 _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^)+(0.1700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1859 _refine_ls_wR_factor_ref 0.1954 _reflns_number_gt 1497 _reflns_number_total 1757 _reflns_threshold_expression >2sigma(I) _cod_data_source_file cg801056csup1.cif _cod_data_source_block 47 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius ; _cod_original_cell_volume 1365.84(19) _cod_original_sg_symbol_H-M P2(1)/c _cod_database_code 4509220 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 C1 C 0.3772(2) 0.62957(7) 0.8877(3) 0.0326(5) Uani 1 1 d . C2 C 0.2929(2) 0.61215(7) 1.0418(4) 0.0392(5) Uani 1 1 d . H2 H 0.3186 0.5842 1.1568 0.047 Uiso 1 1 calc R C3 C 0.1714(2) 0.63516(8) 1.0292(4) 0.0439(6) Uani 1 1 d . H3 H 0.1134 0.6230 1.1340 0.053 Uiso 1 1 calc R C4 C 0.1352(2) 0.67608(8) 0.8623(4) 0.0421(6) Uani 1 1 d . H4 H 0.0517 0.6920 0.8513 0.051 Uiso 1 1 calc R C5 C 0.2202(2) 0.69391(7) 0.7116(4) 0.0389(6) Uani 1 1 d . H5 H 0.1938 0.7220 0.5980 0.047 Uiso 1 1 calc R C6 C 0.3436(2) 0.67173(6) 0.7221(3) 0.0313(5) Uani 1 1 d . C7 C 0.4329(2) 0.69286(6) 0.5679(4) 0.0354(5) Uani 1 1 d . H7 H 0.3908 0.7085 0.4010 0.042 Uiso 1 1 calc R C8 C 0.5669(2) 0.69274(6) 0.6339(4) 0.0348(5) Uani 1 1 d . H8 H 0.6091 0.7081 0.5082 0.042 Uiso 1 1 calc R C9 C 0.6555(2) 0.67158(6) 0.8786(4) 0.0316(5) Uani 1 1 d . C10 C 0.7797(2) 0.69398(7) 0.9904(4) 0.0383(6) Uani 1 1 d . H10 H 0.8062 0.7218 0.9017 0.046 Uiso 1 1 calc R C11 C 0.8644(2) 0.67636(8) 1.2271(4) 0.0417(6) Uani 1 1 d . H11 H 0.9475 0.6924 1.3008 0.050 Uiso 1 1 calc R C12 C 0.8283(2) 0.63537(8) 1.3564(4) 0.0457(6) Uani 1 1 d . H12 H 0.8867 0.6231 1.5185 0.055 Uiso 1 1 calc R C13 C 0.7073(2) 0.61226(7) 1.2494(4) 0.0392(6) Uani 1 1 d . H13 H 0.6816 0.5844 1.3396 0.047 Uiso 1 1 calc R C14 C 0.6230(2) 0.62968(7) 1.0093(4) 0.0317(5) Uani 1 1 d . C15 C 0.49990(19) 0.56038(6) 0.7524(3) 0.0340(5) Uani 1 1 d . N1 N 0.50012(15) 0.60384(5) 0.8935(3) 0.0327(5) Uani 1 1 d . N2 N 0.38757(18) 0.54078(5) 0.6327(4) 0.0382(5) Uani 1 1 d . H2A H 0.3859 0.5131 0.5405 0.046 Uiso 1 1 calc R H2B H 0.3121 0.5551 0.6427 0.046 Uiso 1 1 calc R O1 O 0.61410(18) 0.54109(5) 0.7449(4) 0.0527(5) Uani 1 1 d . 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 C1 0.0323(12) 0.0338(10) 0.0304(9) -0.0065(7) 0.0052(8) -0.0030(7) C2 0.0381(12) 0.0412(11) 0.0378(10) -0.0021(8) 0.0084(9) -0.0049(9) C3 0.0363(13) 0.0553(13) 0.0420(11) -0.0077(9) 0.0134(10) -0.0092(9) C4 0.0296(12) 0.0489(12) 0.0456(11) -0.0133(9) 0.0049(9) 0.0019(9) C5 0.0348(12) 0.0404(11) 0.0376(10) -0.0055(8) 0.0017(9) 0.0008(8) C6 0.0299(11) 0.0326(10) 0.0291(9) -0.0057(7) 0.0030(8) -0.0029(7) C7 0.0390(12) 0.0330(10) 0.0322(9) 0.0014(7) 0.0051(9) 0.0005(8) C8 0.0375(12) 0.0345(10) 0.0340(9) 0.0006(7) 0.0118(9) -0.0013(8) C9 0.0318(12) 0.0299(9) 0.0340(9) -0.0051(7) 0.0097(8) 0.0022(7) C10 0.0339(13) 0.0371(10) 0.0459(10) -0.0057(8) 0.0137(9) -0.0016(8) C11 0.0272(12) 0.0516(12) 0.0454(11) -0.0128(9) 0.0071(9) -0.0001(9) C12 0.0382(14) 0.0592(13) 0.0356(10) -0.0048(8) 0.0012(10) 0.0092(9) C13 0.0381(12) 0.0420(11) 0.0376(10) 0.0027(8) 0.0098(9) 0.0070(9) C14 0.0290(11) 0.0309(9) 0.0351(10) -0.0053(7) 0.0075(8) 0.0032(7) C15 0.0443(13) 0.0269(9) 0.0315(9) 0.0036(7) 0.0106(9) 0.0027(8) N1 0.0332(10) 0.0277(9) 0.0369(8) -0.0019(6) 0.0078(7) 0.0005(6) N2 0.0389(11) 0.0271(8) 0.0468(9) -0.0130(6) 0.0074(8) -0.0011(7) O1 0.0572(11) 0.0432(9) 0.0579(10) -0.0078(7) 0.0145(8) 0.0047(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C2 C1 C6 121.01(19) C2 C1 N1 119.73(17) C6 C1 N1 119.25(18) C3 C2 C1 120.48(19) C3 C2 H2 119.8 C1 C2 H2 119.8 C2 C3 C4 119.3(2) C2 C3 H3 120.3 C4 C3 H3 120.3 C5 C4 C3 120.2(2) C5 C4 H4 119.9 C3 C4 H4 119.9 C4 C5 C6 121.69(19) C4 C5 H5 119.2 C6 C5 H5 119.2 C5 C6 C1 117.26(19) C5 C6 C7 120.02(17) C1 C6 C7 122.72(18) C8 C7 C6 127.68(16) C8 C7 H7 116.2 C6 C7 H7 116.2 C7 C8 C9 127.10(19) C7 C8 H8 116.4 C9 C8 H8 116.4 C14 C9 C10 117.38(18) C14 C9 C8 123.16(19) C10 C9 C8 119.46(17) C11 C10 C9 121.4(2) C11 C10 H10 119.3 C9 C10 H10 119.3 C12 C11 C10 120.0(2) C12 C11 H11 120.0 C10 C11 H11 120.0 C13 C12 C11 119.80(18) C13 C12 H12 120.1 C11 C12 H12 120.1 C12 C13 C14 120.1(2) C12 C13 H13 120.0 C14 C13 H13 120.0 C9 C14 C13 121.2(2) C9 C14 N1 119.35(16) C13 C14 N1 119.42(18) N2 C15 O1 122.79(17) N2 C15 N1 118.98(17) O1 C15 N1 118.23(16) C15 N1 C14 121.02(15) C15 N1 C1 120.86(14) C14 N1 C1 117.16(14) C15 N2 H2A 120.0 C15 N2 H2B 120.0 H2A N2 H2B 120.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.385(3) C1 C6 1.406(3) C1 N1 1.438(2) C2 C3 1.385(3) C2 H2 0.9500 C3 C4 1.385(3) C3 H3 0.9500 C4 C5 1.382(3) C4 H4 0.9500 C5 C6 1.394(3) C5 H5 0.9500 C6 C7 1.462(3) C7 C8 1.337(3) C7 H7 0.9500 C8 C9 1.464(3) C8 H8 0.9500 C9 C14 1.392(3) C9 C10 1.402(3) C10 C11 1.383(3) C10 H10 0.9500 C11 C12 1.382(3) C11 H11 0.9500 C12 C13 1.380(3) C12 H12 0.9500 C13 C14 1.392(3) C13 H13 0.9500 C14 N1 1.437(2) C15 N2 1.281(2) C15 O1 1.295(2) C15 N1 1.373(2) N2 H2A 0.8800 N2 H2B 0.8800 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A O1 0.88 2.06 2.920(2) 167.0 3_666 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 C6 C1 C2 C3 2.0(3) N1 C1 C2 C3 -177.09(16) C1 C2 C3 C4 -0.5(3) C2 C3 C4 C5 -0.5(3) C3 C4 C5 C6 -0.1(3) C4 C5 C6 C1 1.5(3) C4 C5 C6 C7 -177.62(16) C2 C1 C6 C5 -2.5(3) N1 C1 C6 C5 176.61(15) C2 C1 C6 C7 176.65(16) N1 C1 C6 C7 -4.3(2) C5 C6 C7 C8 147.79(19) C1 C6 C7 C8 -31.3(3) C6 C7 C8 C9 -0.5(3) C7 C8 C9 C14 32.4(3) C7 C8 C9 C10 -147.54(19) C14 C9 C10 C11 -2.4(3) C8 C9 C10 C11 177.55(17) C9 C10 C11 C12 1.0(3) C10 C11 C12 C13 -0.3(3) C11 C12 C13 C14 1.1(3) C10 C9 C14 C13 3.3(3) C8 C9 C14 C13 -176.73(17) C10 C9 C14 N1 -176.53(15) C8 C9 C14 N1 3.5(3) C12 C13 C14 C9 -2.7(3) C12 C13 C14 N1 177.12(17) N2 C15 N1 C14 -174.08(16) O1 C15 N1 C14 5.5(2) N2 C15 N1 C1 -5.6(3) O1 C15 N1 C1 173.97(16) C9 C14 N1 C15 102.5(2) C13 C14 N1 C15 -77.3(2) C9 C14 N1 C1 -66.3(2) C13 C14 N1 C1 113.86(19) C2 C1 N1 C15 76.8(2) C6 C1 N1 C15 -102.33(19) C2 C1 N1 C14 -114.36(19) C6 C1 N1 C14 66.6(2) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.000 -0.055 115.5 48.1 2 0.000 0.500 -0.070 115.5 48.1