#------------------------------------------------------------------------------ #$Date: 2011-01-02 22:00:31 +0200 (Sun, 02 Jan 2011) $ #$Revision: 5310 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2216052.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_2216052 loop_ _publ_author_name 'Fernandes, Philippe' 'Bardin, Julie' 'Johnston, Andrea' 'Florence, Alastair J.' 'Leech, Charlotte K.' 'David, William I. F.' 'Shankland, Kenneth' _publ_section_title ; Carbamazepine trifluoroacetic acid solvate ; _journal_coeditor_code LW2031 _journal_issue 11 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o4269 _journal_page_last o4269 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C15 H12 N2 O, C2 H F3 O2' _chemical_formula_moiety 'C15 H12 N2 O, C2 H F3 O2' _chemical_formula_sum 'C17 H13 F3 N2 O3' _chemical_formula_weight 350.29 _chemical_name_common 'Carbamazepine trifluoroacetic acid solvate' _chemical_name_systematic ; 5H-dibenzo[b,f]azepine-5-carboxamide trifluoroacetic acid solvate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 101.735(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 15.0142(4) _cell_length_b 5.28710(10) _cell_length_c 20.2489(6) _cell_measurement_reflns_used 5963 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 28.5791 _cell_measurement_theta_min 2.7447 _cell_volume 1573.79(7) _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2006)' _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2006)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2006)' _computing_molecular_graphics 'PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'enCIFer (Allen et al., 2004) and publCIF (Westrip, 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 15.9745 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Oxford Diffraction Gemini' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 14283 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.77 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.91367 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(CrysAlis RED; Oxford Diffraction, 2006)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 720 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.182 _refine_diff_density_min -0.201 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 266 _refine_ls_number_reflns 3219 _refine_ls_number_restraints 31 _refine_ls_restrained_S_all 1.288 _refine_ls_R_factor_all 0.0589 _refine_ls_R_factor_gt 0.0386 _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^)+(0.0497P)^2^+0.1509P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0937 _refine_ls_wR_factor_ref 0.1018 _reflns_number_gt 2345 _reflns_number_total 3219 _reflns_threshold_expression I>2sigma(I) _[local]_cod_data_source_file lw2031.cif _[local]_cod_cif_authors_sg_H-M 'P 21/n ' _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 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius ; _cod_database_code 2216052 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 _atom_site_disorder_assembly _atom_site_disorder_group O O1 0.61349(8) 0.1916(2) 0.88720(6) 0.0347(3) Uani d . 1 . . O O2 0.73657(9) -0.1001(3) 0.93120(6) 0.0425(4) Uani d D 1 . . N N1 0.50894(9) 0.3825(3) 0.80755(7) 0.0278(3) Uani d . 1 . . C C15 0.58756(12) 0.2517(3) 0.82554(8) 0.0277(4) Uani d . 1 . . N N2 0.63435(12) 0.1896(3) 0.77939(9) 0.0370(4) Uani d . 1 . . C C1 0.45500(12) 0.4356(3) 0.85706(8) 0.0281(4) Uani d . 1 . . C C13 0.49565(13) 0.6039(3) 0.69997(9) 0.0343(4) Uani d . 1 . . H H10 0.5419 0.7178 0.7206 0.041 Uiso calc R 1 . . C C8 0.35742(12) 0.0624(3) 0.74805(9) 0.0336(4) Uani d . 1 . . H H6 0.3343 -0.0869 0.7245 0.040 Uiso calc R 1 . . C C3 0.43009(13) 0.6803(4) 0.95088(9) 0.0367(5) Uani d . 1 . . H H2 0.4455 0.8194 0.9807 0.044 Uiso calc R 1 . . C C9 0.39615(12) 0.2490(3) 0.70935(9) 0.0294(4) Uani d . 1 . . C C7 0.35033(12) 0.0752(3) 0.81274(9) 0.0330(4) Uani d . 1 . . H H5 0.3216 -0.0643 0.8294 0.040 Uiso calc R 1 . . O O3 0.78814(11) -0.1266(3) 0.83537(7) 0.0581(5) Uani d . 1 . . C C2 0.47840(12) 0.6364(3) 0.90077(9) 0.0321(4) Uani d . 1 . . H H1 0.5276 0.7439 0.8964 0.038 Uiso calc R 1 . . C C10 0.36087(12) 0.2735(4) 0.63999(9) 0.0348(4) Uani d . 1 . . H H7 0.3151 0.1593 0.6187 0.042 Uiso calc R 1 . . C C6 0.38155(11) 0.2784(3) 0.86079(8) 0.0292(4) Uani d . 1 . . C C5 0.33566(12) 0.3238(4) 0.91326(9) 0.0353(4) Uani d . 1 . . H H4 0.2870 0.2156 0.9184 0.042 Uiso calc R 1 . . C C16 0.78678(13) -0.1839(4) 0.89305(10) 0.0378(5) Uani d . 1 A . C C4 0.35940(13) 0.5216(4) 0.95756(9) 0.0380(5) Uani d . 1 . . H H3 0.3271 0.5489 0.9927 0.046 Uiso calc R 1 . . C C14 0.46605(11) 0.4149(3) 0.73755(8) 0.0280(4) Uani d . 1 . . C C12 0.45728(13) 0.6257(4) 0.63196(9) 0.0391(5) Uani d . 1 . . H H9 0.4768 0.7558 0.6058 0.047 Uiso calc R 1 . . C C11 0.39068(13) 0.4580(4) 0.60228(9) 0.0383(5) Uani d . 1 . . H H8 0.3654 0.4706 0.5554 0.046 Uiso calc R 1 . . C C17 0.85526(15) -0.3839(4) 0.92652(11) 0.0485(6) Uani d D 1 . . F F1 0.8383(4) -0.4625(10) 0.9861(2) 0.0683(15) Uani d PD 0.531(10) A 1 F F2 0.8464(4) -0.5985(7) 0.8905(2) 0.0780(18) Uani d PD 0.531(10) A 1 F F3 0.9375(2) -0.3149(10) 0.9393(4) 0.078(2) Uani d PD 0.531(10) A 1 F F2A 0.9013(5) -0.4712(16) 0.88091(17) 0.093(3) Uani d PD 0.469(10) A 2 F F1A 0.8259(5) -0.5511(14) 0.9580(6) 0.125(4) Uani d PD 0.469(10) A 2 F F3A 0.9226(4) -0.2545(11) 0.9669(3) 0.089(2) Uani d PD 0.469(10) A 2 H H11 0.6226(15) 0.257(4) 0.7391(12) 0.052(7) Uiso d . 1 . . H H12 0.6879(16) 0.108(4) 0.7928(11) 0.055(7) Uiso d . 1 . . H H13 0.6928(16) 0.008(4) 0.9118(12) 0.084(8) Uiso d 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 O1 0.0331(7) 0.0466(8) 0.0232(7) 0.0093(6) 0.0028(5) 0.0017(6) O2 0.0423(8) 0.0537(9) 0.0320(7) 0.0178(7) 0.0083(6) 0.0050(6) N1 0.0255(7) 0.0352(8) 0.0212(8) 0.0000(6) 0.0015(6) 0.0017(6) C15 0.0262(9) 0.0312(9) 0.0244(9) -0.0030(7) 0.0022(7) -0.0009(8) N2 0.0327(9) 0.0523(10) 0.0259(9) 0.0084(8) 0.0056(7) 0.0033(8) C1 0.0277(9) 0.0325(10) 0.0220(9) 0.0067(7) 0.0003(7) 0.0047(7) C13 0.0376(10) 0.0366(10) 0.0278(10) -0.0031(8) 0.0048(8) -0.0002(8) C8 0.0329(10) 0.0301(10) 0.0358(11) -0.0015(8) 0.0021(8) -0.0022(8) C3 0.0438(11) 0.0375(11) 0.0254(10) 0.0082(9) -0.0008(8) -0.0006(8) C9 0.0286(9) 0.0305(9) 0.0277(10) 0.0023(7) 0.0026(7) -0.0004(7) C7 0.0295(9) 0.0322(10) 0.0359(11) -0.0018(8) 0.0031(8) 0.0056(8) O3 0.0580(10) 0.0832(11) 0.0354(9) 0.0306(9) 0.0153(7) 0.0042(8) C2 0.0353(10) 0.0326(10) 0.0257(9) 0.0014(8) 0.0002(8) 0.0048(8) C10 0.0296(9) 0.0432(11) 0.0291(10) 0.0000(8) -0.0002(8) -0.0039(9) C6 0.0265(9) 0.0314(10) 0.0277(9) 0.0046(7) 0.0010(7) 0.0059(8) C5 0.0270(9) 0.0470(11) 0.0309(10) 0.0034(8) 0.0037(8) 0.0080(9) C16 0.0353(10) 0.0465(12) 0.0309(11) 0.0059(9) 0.0050(8) -0.0051(9) C4 0.0353(10) 0.0512(12) 0.0263(10) 0.0138(9) 0.0033(8) 0.0043(9) C14 0.0270(9) 0.0331(10) 0.0231(9) 0.0031(7) 0.0032(7) -0.0002(7) C12 0.0444(11) 0.0426(11) 0.0310(10) 0.0024(9) 0.0092(9) 0.0084(9) C11 0.0387(11) 0.0496(12) 0.0245(10) 0.0067(9) 0.0013(8) 0.0016(9) C17 0.0459(13) 0.0552(14) 0.0436(13) 0.0144(11) 0.0071(11) -0.0038(12) F1 0.078(3) 0.068(3) 0.062(2) 0.043(2) 0.0242(17) 0.0320(19) F2 0.090(3) 0.051(2) 0.090(3) 0.022(2) 0.009(2) -0.0199(18) F3 0.0276(16) 0.068(3) 0.137(6) 0.0041(16) 0.015(2) 0.043(3) F2A 0.104(5) 0.119(5) 0.057(2) 0.082(5) 0.016(2) -0.002(3) F1A 0.083(4) 0.061(4) 0.252(11) 0.030(3) 0.082(6) 0.076(6) F3A 0.062(3) 0.134(4) 0.061(3) 0.048(3) -0.015(2) -0.011(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' F F 0.0171 0.0103 '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 C16 O2 H13 115.4(14) C15 N1 C1 119.75(13) C15 N1 C14 121.05(14) C1 N1 C14 117.35(13) O1 C15 N2 122.21(16) O1 C15 N1 117.95(15) N2 C15 N1 119.84(16) C15 N2 H11 121.6(14) C15 N2 H12 118.4(14) H11 N2 H12 118(2) C2 C1 C6 121.60(17) C2 C1 N1 119.38(16) C6 C1 N1 118.99(15) C14 C13 C12 119.48(17) C14 C13 H10 120.3 C12 C13 H10 120.3 C7 C8 C9 127.90(17) C7 C8 H6 116.0 C9 C8 H6 116.0 C4 C3 C2 119.91(18) C4 C3 H2 120.0 C2 C3 H2 120.0 C14 C9 C10 116.76(16) C14 C9 C8 123.75(16) C10 C9 C8 119.46(16) C8 C7 C6 127.64(17) C8 C7 H5 116.2 C6 C7 H5 116.2 C1 C2 C3 119.78(18) C1 C2 H1 120.1 C3 C2 H1 120.1 C11 C10 C9 121.66(17) C11 C10 H7 119.2 C9 C10 H7 119.2 C1 C6 C5 117.10(16) C1 C6 C7 123.50(16) C5 C6 C7 119.39(17) C4 C5 C6 121.51(18) C4 C5 H4 119.2 C6 C5 H4 119.2 O3 C16 O2 129.10(18) O3 C16 C17 117.23(18) O2 C16 C17 113.66(17) C5 C4 C3 120.00(18) C5 C4 H3 120.0 C3 C4 H3 120.0 C13 C14 C9 121.82(16) C13 C14 N1 119.83(15) C9 C14 N1 118.34(15) C11 C12 C13 119.85(18) C11 C12 H9 120.1 C13 C12 H9 120.1 C10 C11 C12 120.34(17) C10 C11 H8 119.8 C12 C11 H8 119.8 F3 C17 F2 110.0(3) F1A C17 F2A 113.6(4) F3 C17 F1 105.0(4) F2 C17 F1 102.1(3) F1A C17 F3A 110.8(5) F2A C17 F3A 99.5(3) F1A C17 C16 116.6(4) F3 C17 C16 115.6(3) F2 C17 C16 111.1(2) F2A C17 C16 109.0(2) F1 C17 C16 112.1(3) F3A C17 C16 105.7(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C15 1.2704(19) O2 C16 1.264(2) O2 H13 0.900(19) N1 C15 1.353(2) N1 C1 1.439(2) N1 C14 1.443(2) C15 N2 1.320(2) N2 H11 0.88(2) N2 H12 0.90(2) C1 C2 1.381(2) C1 C6 1.395(2) C13 C14 1.383(2) C13 C12 1.385(3) C13 H10 0.9500 C8 C7 1.337(2) C8 C9 1.453(3) C8 H6 0.9500 C3 C4 1.381(3) C3 C2 1.382(3) C3 H2 0.9500 C9 C14 1.398(2) C9 C10 1.403(2) C7 C6 1.461(2) C7 H5 0.9500 O3 C16 1.211(2) C2 H1 0.9500 C10 C11 1.369(3) C10 H7 0.9500 C6 C5 1.400(3) C5 C4 1.377(3) C5 H4 0.9500 C16 C17 1.533(3) C4 H3 0.9500 C12 C11 1.379(3) C12 H9 0.9500 C11 H8 0.9500 C17 F1A 1.223(5) C17 F3 1.263(4) C17 F2 1.340(3) C17 F2A 1.343(4) C17 F1 1.348(4) C17 F3A 1.350(5) 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 _geom_hbond_publ_flag N2 H11 O3 2_656 0.88(2) 2.30(2) 2.966(2) 134(2) yes N2 H12 O3 . 0.90(2) 2.01(2) 2.889(2) 166(2) yes O2 H13 O1 . 0.90(2) 1.54(2) 2.4326(18) 173(2) yes