Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Thomas Gelbrich' _publ_contact_author_address ; School of Chemistry University of Southampton Highfield Southampton SO171BJ UNITED KINGDOM ; _publ_contact_author_email GELBRICH@SOTON.AC.UK _publ_section_title ; Systematic investigation of the relationships between 25 crystal structures containing the carbamazepine molecule or a close analogue - a case study of the XPac method ; loop_ _publ_author_name 'Thomas Gelbrich' 'M. Hursthouse' # Attachment 'neu.cif' data_s92 _database_code_depnum_ccdc_archive 'CCDC 295483' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 N2 O3' _chemical_formula_weight 272.30 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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' _cell_length_a 10.1051(6) _cell_length_b 28.8085(18) _cell_length_c 4.8380(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.868(10) _cell_angle_gamma 90.00 _cell_volume 1367.35(13) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9816 _exptl_absorpt_correction_T_max 0.9953 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14361 _diffrn_reflns_av_R_equivalents 0.1094 _diffrn_reflns_av_sigmaI/netI 0.0804 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.24 _reflns_number_total 2441 _reflns_number_gt 1487 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0057P)^2^+0.1000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0152(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2441 _refine_ls_number_parameters 203 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.1038 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.0856 _refine_ls_wR_factor_gt 0.0770 _refine_ls_goodness_of_fit_ref 1.171 _refine_ls_restrained_S_all 1.168 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 N1 N -0.0028(6) 0.61063(6) 0.2298(4) 0.0226(5) Uani 1 1 d . . . N2 N -0.1157(4) 0.54675(15) 0.3411(12) 0.0227(7) Uani 1 1 d DU . . H1N H -0.1970(16) 0.5582(9) 0.267(6) 0.028(9) Uiso 1 1 d D . . H2N H -0.109(3) 0.5193(6) 0.423(7) 0.057(12) Uiso 1 1 d D . . O1 O 0.1154(4) 0.54729(13) 0.4501(10) 0.0337(8) Uani 1 1 d D . . C1 C 0.1208(4) 0.63465(17) 0.2250(11) 0.0209(14) Uani 1 1 d D . . C2 C 0.1551(4) 0.67493(17) 0.3882(12) 0.0221(15) Uani 1 1 d D . . C3 C 0.0665(5) 0.69557(17) 0.5552(12) 0.0219(14) Uani 1 1 d D . . H3 H 0.1093 0.7096 0.7317 0.026 Uiso 1 1 calc R . . C4 C 0.2788(4) 0.69676(16) 0.3826(11) 0.0237(16) Uani 1 1 d D . . H4 H 0.3036 0.7246 0.4880 0.028 Uiso 1 1 calc R . . C5 C 0.3647(4) 0.67881(17) 0.2282(13) 0.0284(17) Uani 1 1 d D . . H5 H 0.4493 0.6936 0.2328 0.034 Uiso 1 1 calc R . . C6 C 0.3275(5) 0.63905(18) 0.0654(12) 0.0265(17) Uani 1 1 d D . . H6 H 0.3851 0.6273 -0.0471 0.032 Uiso 1 1 calc R . . C7 C 0.2069(5) 0.61664(16) 0.0671(13) 0.0286(16) Uani 1 1 d D . . H7 H 0.1829 0.5889 -0.0397 0.034 Uiso 1 1 calc R . . C8 C -0.1276(5) 0.63402(16) 0.1036(11) 0.0215(14) Uani 1 1 d D . . C9 C -0.1596(5) 0.67518(16) 0.2282(11) 0.0242(15) Uani 1 1 d D . . C10 C -0.0695(5) 0.69614(16) 0.4787(11) 0.0263(15) Uani 1 1 d D . . H10 H -0.1133 0.7123 0.6032 0.032 Uiso 1 1 calc R . . C11 C -0.2840(4) 0.69645(17) 0.1015(11) 0.0266(17) Uani 1 1 d D . . H11 H -0.3111 0.7234 0.1871 0.032 Uiso 1 1 calc R . . C12 C -0.3676(5) 0.67925(17) -0.1440(11) 0.0240(15) Uani 1 1 d D . . H12 H -0.4497 0.6951 -0.2294 0.029 Uiso 1 1 calc R . . C13 C -0.3338(5) 0.63927(17) -0.2677(12) 0.0269(17) Uani 1 1 d D . . H13 H -0.3931 0.6271 -0.4347 0.032 Uiso 1 1 calc R . . C14 C -0.2130(5) 0.61713(17) -0.1462(11) 0.0232(14) Uani 1 1 d D . . H14 H -0.1876 0.5901 -0.2336 0.028 Uiso 1 1 calc R . . C15 C 0.0032(5) 0.56663(7) 0.3440(5) 0.0238(5) Uani 1 1 d DU . . O2 O 0.4138(4) 0.54758(15) 0.6503(13) 0.0398(13) Uani 1 1 d D . . H1O H 0.472(2) 0.5543(15) 0.543(5) 0.048 Uiso 1 1 d D . . H2O H 0.3284(12) 0.5551(11) 0.557(6) 0.048 Uiso 1 1 d D . . O3 O 0.4208(4) 0.45140(14) 0.7638(12) 0.0445(13) Uani 1 1 d D . . H3O H 0.445(4) 0.4496(16) 0.955(2) 0.053 Uiso 1 1 d D . . H4O H 0.423(3) 0.4821(4) 0.732(8) 0.053 Uiso 1 1 d 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 N1 0.0218(12) 0.0171(10) 0.0296(18) 0.0017(10) 0.008(3) -0.005(3) N2 0.0245(15) 0.0153(14) 0.0285(18) 0.0013(13) 0.007(2) 0.0027(17) O1 0.0271(18) 0.0265(17) 0.047(2) 0.0114(15) 0.007(2) 0.0030(16) C1 0.016(3) 0.024(4) 0.020(3) 0.006(3) -0.001(3) 0.002(3) C2 0.014(3) 0.031(3) 0.019(4) 0.007(3) 0.000(3) -0.003(2) C3 0.024(3) 0.023(3) 0.018(3) -0.008(3) 0.003(3) 0.006(3) C4 0.035(3) 0.015(3) 0.021(4) 0.001(3) 0.007(3) 0.005(3) C5 0.018(3) 0.023(3) 0.043(5) 0.009(4) 0.005(4) 0.002(3) C6 0.030(3) 0.029(4) 0.024(4) -0.003(3) 0.014(3) 0.000(3) C7 0.034(3) 0.009(3) 0.041(4) 0.008(3) 0.005(3) 0.005(3) C8 0.023(3) 0.014(3) 0.028(4) 0.002(3) 0.007(3) -0.001(3) C9 0.035(3) 0.013(3) 0.025(4) 0.001(3) 0.009(3) -0.005(3) C10 0.034(3) 0.019(3) 0.026(4) 0.010(3) 0.009(4) 0.004(3) C11 0.015(3) 0.029(4) 0.038(5) 0.004(3) 0.012(3) 0.005(3) C12 0.025(3) 0.027(4) 0.021(4) 0.005(4) 0.006(3) 0.002(3) C13 0.022(3) 0.024(4) 0.033(4) 0.008(3) 0.005(3) -0.005(3) C14 0.027(3) 0.027(3) 0.016(3) -0.005(3) 0.007(3) 0.001(3) C15 0.0257(13) 0.0168(12) 0.0287(15) 0.0003(10) 0.006(2) 0.0027(19) O2 0.038(2) 0.039(3) 0.040(3) 0.005(3) 0.006(2) 0.010(2) O3 0.076(3) 0.025(2) 0.027(3) 0.002(3) 0.002(2) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 N1 C15 1.378(3) . ? N1 C8 1.431(6) . ? N1 C1 1.433(6) . ? N2 C15 1.328(2) . ? N2 H1N 0.878(10) . ? N2 H2N 0.879(10) . ? O1 C15 1.257(2) . ? C1 C7 1.389(4) . ? C1 C2 1.399(4) . ? C2 C4 1.405(4) . ? C2 C3 1.469(4) . ? C3 C10 1.335(3) . ? C3 H3 0.9500 . ? C4 C5 1.375(4) . ? C4 H4 0.9500 . ? C5 C6 1.390(4) . ? C5 H5 0.9500 . ? C6 C7 1.381(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C14 1.393(4) . ? C8 C9 1.402(4) . ? C9 C11 1.401(4) . ? C9 C10 1.461(4) . ? C10 H10 0.9500 . ? C11 C12 1.374(4) . ? C11 H11 0.9500 . ? C12 C13 1.378(4) . ? C12 H12 0.9500 . ? C13 C14 1.378(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? O2 H1O 0.895(8) . ? O2 H2O 0.900(8) . ? O3 H3O 0.899(8) . ? O3 H4O 0.899(8) . ? 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 C8 123.6(4) . . ? C15 N1 C1 119.7(4) . . ? C8 N1 C1 116.64(17) . . ? C15 N2 H1N 126.7(19) . . ? C15 N2 H2N 114(2) . . ? H1N N2 H2N 119(3) . . ? C7 C1 C2 121.1(4) . . ? C7 C1 N1 119.5(4) . . ? C2 C1 N1 119.4(4) . . ? C1 C2 C4 117.5(4) . . ? C1 C2 C3 123.0(4) . . ? C4 C2 C3 119.5(4) . . ? C10 C3 C2 125.1(6) . . ? C10 C3 H3 117.4 . . ? C2 C3 H3 117.4 . . ? C5 C4 C2 121.5(4) . . ? C5 C4 H4 119.2 . . ? C2 C4 H4 119.2 . . ? C4 C5 C6 119.8(4) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C7 C6 C5 120.1(4) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C1 119.9(4) . . ? C6 C7 H7 120.0 . . ? C1 C7 H7 120.0 . . ? C14 C8 C9 120.6(4) . . ? C14 C8 N1 120.3(4) . . ? C9 C8 N1 119.0(3) . . ? C11 C9 C8 117.2(4) . . ? C11 C9 C10 119.8(4) . . ? C8 C9 C10 123.0(4) . . ? C3 C10 C9 128.4(6) . . ? C3 C10 H10 115.8 . . ? C9 C10 H10 115.8 . . ? C12 C11 C9 121.5(4) . . ? C12 C11 H11 119.3 . . ? C9 C11 H11 119.3 . . ? C11 C12 C13 120.7(4) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 119.2(4) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C8 120.6(4) . . ? C13 C14 H14 119.7 . . ? C8 C14 H14 119.7 . . ? O1 C15 N2 122.5(2) . . ? O1 C15 N1 121.4(4) . . ? N2 C15 N1 116.1(4) . . ? H1O O2 H2O 109.8(14) . . ? H3O O3 H4O 103(4) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.225 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.054