# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 loop_ _publ_author_name _publ_author_address J.-B.Arlin ; Solid-State Research Group, Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, 27 Taylor Street, Glasgow G4 0NR, U.K. ; L.S.Price ; Department of Chemistry University College London, 20 Gordon Street, London WC1H 0AJ, U.K. ; S.L.Price ; Department of Chemistry University College London, 20 Gordon Street, London WC1H 0AJ, U.K. ; A.J.Florence ; Solid-State Research Group, Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, 27 Taylor Street, Glasgow G4 0NR, U.K. ; _publ_contact_author_address ; Solid-State Research Group, Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, 27 Taylor Street, Glasgow G4 0NR, Scotland. ; _publ_contact_author_email alastair.florence@strath.ac.uk _publ_contact_author_fax +44(0)1415522562 _publ_contact_author_phone +44(0)1415484877 _publ_contact_author_name 'Prof Alastair J. Florence' data_CBZ_form_V _database_code_depnum_ccdc_archive 'CCDC 791775' #TrackingRef '- Supporting information - cbzV.cif' _audit_creation_method SHELXL-97 _publ_section_acknowledgements ; The authors thank EPSRC for funding this work through the Basic Technology program Control and Prediction of the Organic Solid-state ( www.cposs.org.uk) ; Drs A. R. Kennedy and Zoltan Gal for assistance with single-crystal diffraction data collection. ; _chemical_name_systematic ; 5H-Dibenz(b,f)azepine-5-carboxamide ; _chemical_name_common 5H-Dibenz(b,f)azepine-5-carboxamide _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 N2 O' _chemical_formula_sum 'C15 H12 N2 O' _chemical_formula_weight 236.27 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 9.1245(5) _cell_length_b 10.4518(5) _cell_length_c 24.8224(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2367.2(2) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 1257 _cell_measurement_theta_min 3.5583 _cell_measurement_theta_max 72.8819 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_preparation sublimation _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.678 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7224 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0268 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5416 _diffrn_reflns_av_R_equivalents 0.0624 _diffrn_reflns_av_sigmaI/netI 0.0825 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 67.96 _reflns_number_total 2140 _reflns_number_gt 1219 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0520P)^2^+0.0000P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2140 _refine_ls_number_parameters 171 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0872 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1018 _refine_ls_wR_factor_gt 0.0924 _refine_ls_goodness_of_fit_ref 0.824 _refine_ls_restrained_S_all 0.824 _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 O1 O 0.35242(16) 0.18634(17) 0.53830(6) 0.0345(4) Uani 1 1 d . . . N2 N 0.55040(19) 0.11287(19) 0.58456(6) 0.0256(4) Uani 1 1 d . . . N1 N 0.5786(2) 0.2216(2) 0.50407(8) 0.0316(5) Uani 1 1 d . . . C2 C 0.4582(2) 0.0653(2) 0.62702(8) 0.0283(5) Uani 1 1 d . . . C7 C 0.4590(2) 0.1288(2) 0.67691(8) 0.0332(6) Uani 1 1 d . . . C14 C 0.7918(2) 0.0233(2) 0.56398(9) 0.0302(5) Uani 1 1 d . . . H14 H 0.7479 -0.0334 0.5388 0.036 Uiso 1 1 calc R . . C3 C 0.3720(2) -0.0401(2) 0.61787(10) 0.0340(6) Uani 1 1 d . . . H3 H 0.3762 -0.0821 0.5840 0.041 Uiso 1 1 calc R . . C15 C 0.7059(2) 0.1079(2) 0.59333(8) 0.0254(5) Uani 1 1 d . . . C9 C 0.6795(3) 0.2703(3) 0.66720(9) 0.0375(6) Uani 1 1 d . . . H9 H 0.7192 0.3513 0.6766 0.045 Uiso 1 1 calc R . . C10 C 0.7675(3) 0.1902(2) 0.63152(8) 0.0292(5) Uani 1 1 d . . . C11 C 0.9203(3) 0.1902(2) 0.63707(9) 0.0347(6) Uani 1 1 d . . . H11 H 0.9652 0.2481 0.6615 0.042 Uiso 1 1 calc R . . C13 C 0.9426(3) 0.0224(2) 0.57180(9) 0.0339(6) Uani 1 1 d . . . H13 H 1.0018 -0.0368 0.5525 0.041 Uiso 1 1 calc R . . C8 C 0.5476(3) 0.2406(3) 0.68810(9) 0.0390(6) Uani 1 1 d . . . H8 H 0.5079 0.3001 0.7131 0.047 Uiso 1 1 calc R . . C1 C 0.4866(2) 0.1754(2) 0.54189(8) 0.0262(5) Uani 1 1 d . . . C12 C 1.0071(2) 0.1071(2) 0.60743(8) 0.0347(6) Uani 1 1 d . . . H12 H 1.1106 0.1084 0.6116 0.042 Uiso 1 1 calc R . . C6 C 0.3621(3) 0.0804(3) 0.71644(9) 0.0449(7) Uani 1 1 d . . . H6 H 0.3573 0.1214 0.7505 0.054 Uiso 1 1 calc R . . C4 C 0.2791(3) -0.0858(3) 0.65758(10) 0.0441(7) Uani 1 1 d . . . H4 H 0.2191 -0.1585 0.6511 0.053 Uiso 1 1 calc R . . C5 C 0.2749(3) -0.0240(3) 0.70703(10) 0.0491(8) Uani 1 1 d . . . H5 H 0.2112 -0.0542 0.7345 0.059 Uiso 1 1 calc R . . H1N H 0.537(3) 0.274(3) 0.4809(10) 0.046(8) Uiso 1 1 d . . . H2N H 0.678(3) 0.224(3) 0.5067(11) 0.055(9) Uiso 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 O1 0.0244(8) 0.0486(11) 0.0304(8) 0.0094(8) -0.0026(7) 0.0021(8) N2 0.0232(9) 0.0344(11) 0.0193(9) 0.0026(8) -0.0012(8) 0.0007(9) N1 0.0269(10) 0.0415(13) 0.0264(10) 0.0098(9) -0.0002(10) 0.0006(10) C2 0.0251(11) 0.0351(13) 0.0246(11) 0.0065(9) 0.0013(10) 0.0091(10) C7 0.0291(12) 0.0480(15) 0.0224(11) 0.0043(10) 0.0002(10) 0.0116(12) C14 0.0323(13) 0.0335(13) 0.0247(11) 0.0043(10) -0.0005(11) 0.0009(11) C3 0.0300(12) 0.0357(14) 0.0363(12) 0.0066(10) 0.0048(11) 0.0050(11) C15 0.0242(11) 0.0295(13) 0.0223(10) 0.0053(9) -0.0013(10) 0.0006(10) C9 0.0412(14) 0.0389(14) 0.0324(12) -0.0061(11) -0.0093(12) 0.0034(12) C10 0.0318(12) 0.0324(13) 0.0235(11) 0.0040(9) -0.0022(11) 0.0019(11) C11 0.0346(12) 0.0425(15) 0.0269(12) 0.0076(11) -0.0086(11) -0.0048(12) C13 0.0292(13) 0.0368(14) 0.0358(13) 0.0080(11) 0.0055(11) 0.0054(11) C8 0.0378(14) 0.0537(17) 0.0255(12) -0.0104(11) -0.0033(12) 0.0127(13) C1 0.0288(12) 0.0263(12) 0.0235(11) -0.0013(9) -0.0024(10) -0.0018(10) C12 0.0253(12) 0.0446(15) 0.0342(12) 0.0160(11) -0.0007(11) 0.0001(12) C6 0.0378(14) 0.074(2) 0.0231(12) 0.0066(12) 0.0013(12) 0.0118(16) C4 0.0318(13) 0.0488(17) 0.0517(16) 0.0196(13) 0.0050(13) 0.0027(13) C5 0.0350(15) 0.073(2) 0.0397(15) 0.0284(15) 0.0070(13) 0.0062(15) _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 O1 C1 1.233(3) . ? N2 C1 1.374(3) . ? N2 C15 1.437(3) . ? N2 C2 1.437(3) . ? N1 C1 1.348(3) . ? N1 H1N 0.88(3) . ? N1 H2N 0.91(3) . ? C2 C3 1.372(3) . ? C2 C7 1.405(3) . ? C7 C6 1.415(3) . ? C7 C8 1.448(4) . ? C14 C15 1.388(3) . ? C14 C13 1.390(3) . ? C14 H14 0.9500 . ? C3 C4 1.386(3) . ? C3 H3 0.9500 . ? C15 C10 1.398(3) . ? C9 C8 1.347(3) . ? C9 C10 1.459(3) . ? C9 H9 0.9500 . ? C10 C11 1.401(3) . ? C11 C12 1.387(3) . ? C11 H11 0.9500 . ? C13 C12 1.383(3) . ? C13 H13 0.9500 . ? C8 H8 0.9500 . ? C12 H12 0.9500 . ? C6 C5 1.370(4) . ? C6 H6 0.9500 . ? C4 C5 1.388(4) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? 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 C15 123.54(19) . . ? C1 N2 C2 118.80(18) . . ? C15 N2 C2 117.04(17) . . ? C1 N1 H1N 114.0(17) . . ? C1 N1 H2N 125.5(19) . . ? H1N N1 H2N 118(3) . . ? C3 C2 C7 121.9(2) . . ? C3 C2 N2 119.4(2) . . ? C7 C2 N2 118.7(2) . . ? C2 C7 C6 116.1(2) . . ? C2 C7 C8 123.6(2) . . ? C6 C7 C8 120.3(2) . . ? C15 C14 C13 119.4(2) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C2 C3 C4 120.7(2) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C14 C15 C10 121.4(2) . . ? C14 C15 N2 120.1(2) . . ? C10 C15 N2 118.5(2) . . ? C8 C9 C10 126.4(2) . . ? C8 C9 H9 116.8 . . ? C10 C9 H9 116.8 . . ? C15 C10 C11 117.8(2) . . ? C15 C10 C9 122.9(2) . . ? C11 C10 C9 119.2(2) . . ? C12 C11 C10 121.1(2) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C12 C13 C14 120.4(2) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C9 C8 C7 127.6(2) . . ? C9 C8 H8 116.2 . . ? C7 C8 H8 116.2 . . ? O1 C1 N1 122.3(2) . . ? O1 C1 N2 121.4(2) . . ? N1 C1 N2 116.3(2) . . ? C13 C12 C11 119.9(2) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C5 C6 C7 122.0(2) . . ? C5 C6 H6 119.0 . . ? C7 C6 H6 119.0 . . ? C3 C4 C5 119.1(3) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 120.3(2) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? 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 C1 N2 C2 C3 72.9(3) . . . . ? C15 N2 C2 C3 -115.9(2) . . . . ? C1 N2 C2 C7 -107.1(2) . . . . ? C15 N2 C2 C7 64.2(3) . . . . ? C3 C2 C7 C6 -2.1(3) . . . . ? N2 C2 C7 C6 177.8(2) . . . . ? C3 C2 C7 C8 -179.6(2) . . . . ? N2 C2 C7 C8 0.3(3) . . . . ? C7 C2 C3 C4 1.7(3) . . . . ? N2 C2 C3 C4 -178.2(2) . . . . ? C13 C14 C15 C10 -1.5(3) . . . . ? C13 C14 C15 N2 178.1(2) . . . . ? C1 N2 C15 C14 -78.9(3) . . . . ? C2 N2 C15 C14 110.3(2) . . . . ? C1 N2 C15 C10 100.7(2) . . . . ? C2 N2 C15 C10 -70.1(3) . . . . ? C14 C15 C10 C11 3.7(3) . . . . ? N2 C15 C10 C11 -175.9(2) . . . . ? C14 C15 C10 C9 -173.1(2) . . . . ? N2 C15 C10 C9 7.3(3) . . . . ? C8 C9 C10 C15 33.7(4) . . . . ? C8 C9 C10 C11 -143.1(3) . . . . ? C15 C10 C11 C12 -2.9(3) . . . . ? C9 C10 C11 C12 174.0(2) . . . . ? C15 C14 C13 C12 -1.7(4) . . . . ? C10 C9 C8 C7 -5.1(4) . . . . ? C2 C7 C8 C9 -31.3(4) . . . . ? C6 C7 C8 C9 151.4(3) . . . . ? C15 N2 C1 O1 -173.9(2) . . . . ? C2 N2 C1 O1 -3.2(3) . . . . ? C15 N2 C1 N1 7.3(3) . . . . ? C2 N2 C1 N1 178.0(2) . . . . ? C14 C13 C12 C11 2.5(3) . . . . ? C10 C11 C12 C13 -0.1(3) . . . . ? C2 C7 C6 C5 1.4(4) . . . . ? C8 C7 C6 C5 178.9(2) . . . . ? C2 C3 C4 C5 -0.4(4) . . . . ? C7 C6 C5 C4 -0.2(4) . . . . ? C3 C4 C5 C6 -0.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 67.96 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.183 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.047