Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 loop_ _publ_author_name _publ_author_address 'Alastair Florence' ; Department of Pharmaceutical Sciences University of Strathclyde 27 Taylor Street Glasgow G4 0NR Scotland ; 'Andrea Johnston' ; Department of Pharmaceutical Sciences University of Strathclyde 27 Taylor Street Glasgow G4 0NR Scotland ; 'Blair F. Johnston' ; WestCHEM Department of Pure & Applied Chemistry University of Strathclyde 295 Cathedral Street Glasgow G1 1XL Scotland ; 'A. R. Kennedy' '' _publ_contact_author_name 'Alastair Florence' _publ_contact_author_address ; Strathclyde Institute of Pharmacy and Biomedical Sciences University of Strathclyde 27 Taylor Street Glasgow G4 0NR UNITED KINGDOM ; _publ_contact_author_email ALASTAIR.FLORENCE@STRATH.AC.UK _publ_section_title ; Targeted crystallisation of novel carbamazepine solvates based on a retrospective Random Forest classification ; _publ_contact_author_fax 01415526443 _publ_contact_author_phone 01415484877 data_CBZDMA _database_code_depnum_ccdc_archive 'CCDC 643264' _chemical_name_systematic ; [5H-dibenz(b,f)azepine-5-carboxamide]N,N-dimethyl acetamide solvate ; _chemical_name_common ;(5H-dibenz(b,f)azepine-5-carboxamide)N,N-dimethyl acetamide solvate ; _chemical_formula_sum 'C19 H21 N3 O2' _chemical_formula_weight 323.39 _exptl_crystal_colour colourless _chemical_melting_point ? _exptl_crystal_description lump _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_preparation ; recyrstallised by slow solvent evaporation from N,N-dimethylacetamide at 278 K. ; _cell_length_a 7.5046(7) _cell_length_b 19.506(2) _cell_length_c 11.7808(13) _cell_angle_alpha 90.00 _cell_angle_beta 96.597(8) _cell_angle_gamma 90.00 _cell_volume 1713.1(3) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 58355 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.00 _exptl_crystal_density_diffrn 1.254 _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_crystal_density_method 'not measured' _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 9611 _diffrn_reflns_av_R_equivalents 0.072 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.02 _diffrn_measured_fraction_theta_max 0.884 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.884 _refine_diff_density_max 0.238 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.049 _audit_creation_method SHELXL-97 _reflns_number_total 2664 _reflns_number_gt 1853 _reflns_threshold_expression I>2\s(I) _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^)+(0.0577P)^2^+1.1497P] 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_number_reflns 2664 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1056 _refine_ls_R_factor_gt 0.0676 _refine_ls_wR_factor_ref 0.1642 _refine_ls_wR_factor_gt 0.1435 _refine_ls_goodness_of_fit_ref 1.167 _refine_ls_restrained_S_all 1.167 _refine_ls_shift/su_max 0.004 _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 0.8248(3) -0.01528(11) 0.08205(17) 0.0440(6) Uani 1 1 d . . . N1 N 0.7216(4) 0.07363(13) 0.1798(2) 0.0418(7) Uani 1 1 d . . . N2 N 0.9641(4) 0.08777(17) 0.0763(2) 0.0463(8) Uani 1 1 d . . . C1 C 0.5905(5) 0.02981(16) 0.2221(3) 0.0415(8) Uani 1 1 d . . . C2 C 0.4338(5) 0.01360(17) 0.1543(3) 0.0468(9) Uani 1 1 d . . . H2 H 0.4131 0.0314 0.0788 0.056 Uiso 1 1 calc R . . C3 C 0.3073(5) -0.02814(17) 0.1948(3) 0.0476(9) Uani 1 1 d . . . H3 H 0.1987 -0.0386 0.1484 0.057 Uiso 1 1 calc R . . C4 C 0.3404(5) -0.05465(17) 0.3042(3) 0.0480(9) Uani 1 1 d . . . H4 H 0.2541 -0.0839 0.3322 0.058 Uiso 1 1 calc R . . C5 C 0.4961(5) -0.03944(17) 0.3731(3) 0.0460(9) Uani 1 1 d . . . H5 H 0.5172 -0.0592 0.4471 0.055 Uiso 1 1 calc R . . C6 C 0.6241(5) 0.00508(16) 0.3351(3) 0.0435(8) Uani 1 1 d . . . C7 C 0.7808(5) 0.02621(18) 0.4122(3) 0.0447(9) Uani 1 1 d . . . C8 C 0.8624(5) 0.08770(19) 0.4159(3) 0.0462(9) Uani 1 1 d . . . C9 C 0.8127(4) 0.14733(16) 0.3441(3) 0.0401(8) Uani 1 1 d . . . C10 C 0.7376(4) 0.14066(16) 0.2289(3) 0.0405(8) Uani 1 1 d . . . C11 C 0.6770(5) 0.19723(18) 0.1667(3) 0.0481(9) Uani 1 1 d . . . H11 H 0.6257 0.1917 0.0897 0.058 Uiso 1 1 calc R . . C12 C 0.6894(5) 0.26175(18) 0.2140(3) 0.0513(9) Uani 1 1 d . . . H12 H 0.6442 0.3004 0.1707 0.062 Uiso 1 1 calc R . . C13 C 0.7690(5) 0.27004(17) 0.3263(3) 0.0491(9) Uani 1 1 d . . . H13 H 0.7804 0.3145 0.3591 0.059 Uiso 1 1 calc R . . C14 C 0.8307(5) 0.21394(17) 0.3893(3) 0.0461(9) Uani 1 1 d . . . H14 H 0.8868 0.2203 0.4651 0.055 Uiso 1 1 calc R . . C15 C 0.8403(4) 0.04584(18) 0.1104(2) 0.0400(8) Uani 1 1 d . . . O2 O 0.1287(8) 0.2166(4) 0.1545(5) 0.0543(12) Uani 0.907(10) 1 d P A 1 N3 N 0.2235(4) 0.29546(19) 0.2872(3) 0.0485(13) Uani 0.907(10) 1 d P A 1 C16 C 0.2056(6) 0.2308(3) 0.2514(4) 0.0476(13) Uani 0.907(10) 1 d P A 1 C17 C 0.2850(12) 0.1763(4) 0.3333(7) 0.065(2) Uani 0.907(10) 1 d P A 1 H17A H 0.2548 0.1309 0.3012 0.098 Uiso 0.907(10) 1 calc PR A 1 H17B H 0.2360 0.1812 0.4065 0.098 Uiso 0.907(10) 1 calc PR A 1 H17C H 0.4156 0.1816 0.3453 0.098 Uiso 0.907(10) 1 calc PR A 1 C18 C 0.3131(6) 0.3164(3) 0.3986(3) 0.0553(14) Uani 0.907(10) 1 d P A 1 H18A H 0.2397 0.3030 0.4585 0.083 Uiso 0.907(10) 1 calc PR A 1 H18B H 0.3292 0.3663 0.3997 0.083 Uiso 0.907(10) 1 calc PR A 1 H18C H 0.4305 0.2940 0.4121 0.083 Uiso 0.907(10) 1 calc PR A 1 C19 C 0.1449(5) 0.34885(18) 0.2112(3) 0.0598(10) Uani 1 1 d . A 1 H19A H 0.2225 0.3574 0.1512 0.090 Uiso 1 1 calc R A 1 H19B H 0.1331 0.3910 0.2548 0.090 Uiso 1 1 calc R A 1 H19C H 0.0263 0.3341 0.1762 0.090 Uiso 1 1 calc R A 1 N4 N 0.264(4) 0.2430(16) 0.326(3) 0.034(11) Uiso 0.093(10) 1 d P A 2 C20 C 0.175(6) 0.272(3) 0.224(4) 0.042(13) Uiso 0.093(10) 1 d P A 2 O3 O 0.111(12) 0.236(4) 0.144(8) 0.10(4) Uiso 0.093(10) 1 d P A 2 C22 C 0.333(6) 0.275(3) 0.423(4) 0.050(12) Uiso 0.093(10) 1 d P A 2 H22A H 0.4341 0.3038 0.4069 0.076 Uiso 0.093(10) 1 d PR A 2 H22B H 0.3736 0.2411 0.4812 0.076 Uiso 0.093(10) 1 d PR A 2 H22C H 0.2398 0.3040 0.4505 0.076 Uiso 0.093(10) 1 d PR A 2 C21 C 0.273(8) 0.160(3) 0.319(4) 0.008(9) Uiso 0.093(10) 1 d P A 2 H21A H 0.1963 0.1444 0.2507 0.012 Uiso 0.093(10) 1 d PR A 2 H21B H 0.2318 0.1401 0.3871 0.012 Uiso 0.093(10) 1 d PR A 2 H21C H 0.3973 0.1458 0.3132 0.012 Uiso 0.093(10) 1 d PR A 2 H8 H 0.964(4) 0.0969(15) 0.478(3) 0.042(8) Uiso 1 1 d . . . H7 H 0.827(5) -0.0084(18) 0.471(3) 0.060(10) Uiso 1 1 d . . . H1N H 1.050(5) 0.0664(18) 0.037(3) 0.059(11) Uiso 1 1 d . . . H2N H 0.996(5) 0.129(2) 0.105(3) 0.070(13) 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 0.0514(15) 0.0427(14) 0.0395(12) -0.0046(10) 0.0119(10) -0.0029(11) N1 0.0462(18) 0.0449(17) 0.0360(15) -0.0037(12) 0.0124(12) -0.0032(14) N2 0.050(2) 0.047(2) 0.0442(17) -0.0086(14) 0.0167(14) -0.0049(16) C1 0.049(2) 0.0388(19) 0.0387(19) -0.0043(14) 0.0133(15) 0.0028(16) C2 0.055(2) 0.048(2) 0.0388(18) -0.0040(15) 0.0077(16) -0.0024(18) C3 0.049(2) 0.050(2) 0.045(2) -0.0081(16) 0.0072(16) -0.0049(17) C4 0.058(3) 0.042(2) 0.047(2) -0.0045(16) 0.0185(17) -0.0056(17) C5 0.057(2) 0.044(2) 0.0382(19) 0.0009(14) 0.0105(16) 0.0007(17) C6 0.050(2) 0.0417(19) 0.0396(18) -0.0029(15) 0.0077(15) 0.0038(17) C7 0.049(2) 0.047(2) 0.0399(19) 0.0046(16) 0.0089(15) 0.0057(18) C8 0.045(2) 0.057(2) 0.0359(19) -0.0023(16) 0.0034(16) 0.0006(18) C9 0.041(2) 0.042(2) 0.0386(18) 0.0000(14) 0.0114(14) 0.0005(15) C10 0.043(2) 0.041(2) 0.0399(18) -0.0031(15) 0.0116(14) -0.0046(15) C11 0.052(2) 0.051(2) 0.0417(19) -0.0007(16) 0.0091(15) -0.0014(17) C12 0.055(2) 0.044(2) 0.055(2) 0.0034(17) 0.0085(17) 0.0028(17) C13 0.055(2) 0.040(2) 0.054(2) -0.0079(16) 0.0157(17) -0.0027(17) C14 0.048(2) 0.052(2) 0.0391(18) -0.0074(16) 0.0106(15) -0.0029(17) C15 0.045(2) 0.044(2) 0.0309(17) -0.0003(14) 0.0068(14) -0.0018(17) O2 0.064(3) 0.058(3) 0.042(2) -0.012(2) 0.0092(16) -0.012(2) N3 0.050(2) 0.053(3) 0.042(2) -0.0067(17) 0.0065(16) -0.0032(17) C16 0.041(3) 0.055(3) 0.050(3) -0.003(2) 0.019(2) -0.004(2) C17 0.064(4) 0.059(6) 0.075(4) -0.001(4) 0.020(3) 0.005(4) C18 0.058(3) 0.068(4) 0.039(2) -0.009(2) 0.0026(18) 0.006(2) C19 0.073(3) 0.052(2) 0.054(2) 0.0030(18) 0.0051(19) -0.005(2) 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 C15 1.240(4) . ? N1 C15 1.387(4) . ? N1 C10 1.429(4) . ? N1 C1 1.435(4) . ? N2 C15 1.334(4) . ? N2 H1N 0.93(4) . ? N2 H2N 0.90(4) . ? C1 C2 1.381(5) . ? C1 C6 1.411(4) . ? C2 C3 1.378(5) . ? C2 H2 0.9500 . ? C3 C4 1.384(5) . ? C3 H3 0.9500 . ? C4 C5 1.376(5) . ? C4 H4 0.9500 . ? C5 C6 1.406(5) . ? C5 H5 0.9500 . ? C6 C7 1.460(5) . ? C7 C8 1.345(5) . ? C7 H7 1.00(4) . ? C8 C9 1.461(5) . ? C8 H8 1.01(3) . ? C9 C14 1.405(4) . ? C9 C10 1.415(4) . ? C10 C11 1.373(4) . ? C11 C12 1.375(5) . ? C11 H11 0.9500 . ? C12 C13 1.397(5) . ? C12 H12 0.9500 . ? C13 C14 1.372(5) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? O2 C16 1.250(7) . ? N3 C16 1.331(7) . ? N3 C19 1.453(5) . ? N3 C18 1.463(5) . ? C16 C17 1.511(9) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C17 H21A 1.2764 . ? C17 H21B 1.0576 . ? C17 H21C 1.0804 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C18 H22A 0.9347 . ? C18 H22C 0.9017 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? N4 C22 1.35(5) . ? N4 C20 1.42(6) . ? N4 C21 1.62(5) . ? C20 O3 1.23(9) . ? C22 H22A 0.9801 . ? C22 H22B 0.9800 . ? C22 H22C 0.9801 . ? C21 H21A 0.9800 . ? C21 H21B 0.9801 . ? C21 H21C 0.9802 . ? 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 C10 124.5(3) . . ? C15 N1 C1 119.0(3) . . ? C10 N1 C1 115.7(2) . . ? C15 N2 H1N 115(2) . . ? C15 N2 H2N 127(2) . . ? H1N N2 H2N 115(3) . . ? C2 C1 C6 121.1(3) . . ? C2 C1 N1 120.5(3) . . ? C6 C1 N1 118.4(3) . . ? C3 C2 C1 120.6(3) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 C4 119.1(3) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 121.2(3) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 120.7(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 117.2(3) . . ? C5 C6 C7 120.5(3) . . ? C1 C6 C7 122.3(3) . . ? C8 C7 C6 127.1(3) . . ? C8 C7 H7 117(2) . . ? C6 C7 H7 115(2) . . ? C7 C8 C9 127.3(3) . . ? C7 C8 H8 119.1(17) . . ? C9 C8 H8 113.4(17) . . ? C14 C9 C10 117.3(3) . . ? C14 C9 C8 120.6(3) . . ? C10 C9 C8 122.0(3) . . ? C11 C10 C9 120.6(3) . . ? C11 C10 N1 120.8(3) . . ? C9 C10 N1 118.6(3) . . ? C10 C11 C12 121.1(3) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C11 C12 C13 119.5(3) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C14 C13 C12 120.0(3) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C9 121.4(3) . . ? C13 C14 H14 119.3 . . ? C9 C14 H14 119.3 . . ? O1 C15 N2 123.7(3) . . ? O1 C15 N1 119.2(3) . . ? N2 C15 N1 117.0(3) . . ? C16 N3 C19 117.7(4) . . ? C16 N3 C18 124.6(4) . . ? C19 N3 C18 117.7(3) . . ? O2 C16 N3 121.2(6) . . ? O2 C16 C17 122.3(6) . . ? N3 C16 C17 116.5(5) . . ? C16 C17 H21A 74.0 . . ? H17A C17 H21A 35.6 . . ? H17B C17 H21A 120.2 . . ? H17C C17 H21A 125.9 . . ? C16 C17 H21B 134.8 . . ? H17A C17 H21B 62.6 . . ? H17B C17 H21B 48.1 . . ? H17C C17 H21B 115.1 . . ? H21A C17 H21B 86.0 . . ? C16 C17 H21C 120.5 . . ? H17A C17 H21C 64.4 . . ? H17B C17 H21C 128.9 . . ? H17C C17 H21C 45.3 . . ? H21A C17 H21C 85.1 . . ? H21B C17 H21C 96.9 . . ? N3 C18 H22A 111.2 . . ? H18A C18 H22A 118.3 . . ? H18B C18 H22A 98.2 . . ? H18C C18 H22A 11.9 . . ? N3 C18 H22C 106.3 . . ? H18A C18 H22C 3.4 . . ? H18B C18 H22C 109.9 . . ? H18C C18 H22C 112.2 . . ? H22A C18 H22C 121.3 . . ? C22 N4 C20 129(4) . . ? C22 N4 C21 120(3) . . ? C20 N4 C21 111(4) . . ? O3 C20 N4 122(6) . . ? N4 C22 H22A 109.4 . . ? N4 C22 H22B 109.6 . . ? H22A C22 H22B 109.5 . . ? N4 C22 H22C 109.4 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N4 C21 H21A 109.5 . . ? N4 C21 H21B 109.4 . . ? H21A C21 H21B 109.5 . . ? N4 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? 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 C15 N1 C1 C2 -81.3(4) . . . . ? C10 N1 C1 C2 108.8(3) . . . . ? C15 N1 C1 C6 100.1(3) . . . . ? C10 N1 C1 C6 -69.8(4) . . . . ? C6 C1 C2 C3 -1.0(5) . . . . ? N1 C1 C2 C3 -179.6(3) . . . . ? C1 C2 C3 C4 -1.0(5) . . . . ? C2 C3 C4 C5 0.7(5) . . . . ? C3 C4 C5 C6 1.7(5) . . . . ? C4 C5 C6 C1 -3.6(5) . . . . ? C4 C5 C6 C7 174.2(3) . . . . ? C2 C1 C6 C5 3.3(5) . . . . ? N1 C1 C6 C5 -178.1(3) . . . . ? C2 C1 C6 C7 -174.4(3) . . . . ? N1 C1 C6 C7 4.2(4) . . . . ? C5 C6 C7 C8 -144.5(4) . . . . ? C1 C6 C7 C8 33.1(5) . . . . ? C6 C7 C8 C9 0.2(6) . . . . ? C7 C8 C9 C14 143.7(4) . . . . ? C7 C8 C9 C10 -33.4(5) . . . . ? C14 C9 C10 C11 -3.2(5) . . . . ? C8 C9 C10 C11 174.0(3) . . . . ? C14 C9 C10 N1 178.5(3) . . . . ? C8 C9 C10 N1 -4.3(5) . . . . ? C15 N1 C10 C11 82.3(4) . . . . ? C1 N1 C10 C11 -108.4(3) . . . . ? C15 N1 C10 C9 -99.4(3) . . . . ? C1 N1 C10 C9 69.8(4) . . . . ? C9 C10 C11 C12 0.7(5) . . . . ? N1 C10 C11 C12 178.9(3) . . . . ? C10 C11 C12 C13 1.6(5) . . . . ? C11 C12 C13 C14 -1.4(5) . . . . ? C12 C13 C14 C9 -1.3(5) . . . . ? C10 C9 C14 C13 3.5(5) . . . . ? C8 C9 C14 C13 -173.7(3) . . . . ? C10 N1 C15 O1 172.5(3) . . . . ? C1 N1 C15 O1 3.5(4) . . . . ? C10 N1 C15 N2 -8.7(4) . . . . ? C1 N1 C15 N2 -177.6(3) . . . . ? C19 N3 C16 O2 2.1(6) . . . . ? C18 N3 C16 O2 -179.3(4) . . . . ? C19 N3 C16 C17 -178.7(5) . . . . ? C18 N3 C16 C17 -0.1(6) . . . . ? C22 N4 C20 O3 -176(6) . . . . ? C21 N4 C20 O3 2(7) . . . . ? _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. ; _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. ; _computing_data_collection 'Denzo & Collect' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' # Attachment 'NMP-CSD-extras.cif' data_CBZ-NMP _database_code_depnum_ccdc_archive 'CCDC 643265' _chemical_name_systematic ; [5H-dibenz(b,f)azepine-5-carboxamide] N-methylpyrrolidine solvate ; _chemical_name_common ;(5H-dibenz(b,f)azepine-5-carboxamide) N-methylpyrrolidine solvate ; _chemical_formula_sum 'C20 H21 N3 O2' _chemical_formula_weight 335.40 _exptl_crystal_colour colourless _exptl_crystal_description 'triangular fragment' _chemical_melting_point ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_preparation ; recyrstallised by slow evaporation from N-methylpyrrolidone at 278 K. ; _cell_length_a 7.5448(4) _cell_length_b 19.5119(10) _cell_length_c 11.8783(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.013(3) _cell_angle_gamma 90.00 _cell_volume 1731.57(15) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3999 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_density_diffrn 1.287 _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 22709 _diffrn_reflns_av_R_equivalents 0.064 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 27.49 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.190 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.040 _audit_creation_method SHELXL-97 _reflns_number_total 3952 _reflns_number_gt 2508 _reflns_threshold_expression I>2\s(I) _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^)+(0.0363P)^2^+0.6268P] 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 3952 _refine_ls_number_parameters 261 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1030 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1174 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 0.67392(16) -0.01515(6) 0.91965(10) 0.0339(3) Uani 1 1 d . . . N1 N 0.76600(19) 0.07235(7) 0.81678(12) 0.0302(4) Uani 1 1 d . . . N2 N 0.5359(2) 0.08762(8) 0.92589(14) 0.0342(4) Uani 1 1 d . . . C1 C 0.8983(2) 0.02929(8) 0.77625(15) 0.0298(4) Uani 1 1 d . . . C2 C 1.0530(2) 0.01286(9) 0.84777(16) 0.0343(4) Uani 1 1 d . . . H2 H 1.0712 0.0297 0.9235 0.041 Uiso 1 1 calc R . . C3 C 1.1812(3) -0.02815(9) 0.80901(17) 0.0369(5) Uani 1 1 d . . . H3 H 1.2886 -0.0389 0.8575 0.044 Uiso 1 1 calc R . . C4 C 1.1518(3) -0.05342(9) 0.69915(17) 0.0383(5) Uani 1 1 d . . . H4 H 1.2389 -0.0821 0.6726 0.046 Uiso 1 1 calc R . . C5 C 0.9974(3) -0.03735(9) 0.62786(16) 0.0356(5) Uani 1 1 d . . . H5 H 0.9780 -0.0559 0.5532 0.043 Uiso 1 1 calc R . . C6 C 0.8682(2) 0.00627(9) 0.66423(15) 0.0309(4) Uani 1 1 d . . . C7 C 0.7155(2) 0.02833(9) 0.58326(16) 0.0362(5) Uani 1 1 d . . . H7 H 0.6683 -0.0042 0.5276 0.043 Uiso 1 1 calc R . . C8 C 0.6346(2) 0.08972(10) 0.57904(16) 0.0353(4) Uani 1 1 d . . . H8 H 0.5365 0.0959 0.5205 0.042 Uiso 1 1 calc R . . C9 C 0.6808(2) 0.14807(9) 0.65470(15) 0.0301(4) Uani 1 1 d . . . C10 C 0.6622(2) 0.21509(9) 0.61106(16) 0.0351(4) Uani 1 1 d . . . H10 H 0.6093 0.2222 0.5346 0.042 Uiso 1 1 calc R . . C11 C 0.7200(3) 0.27067(9) 0.67821(17) 0.0404(5) Uani 1 1 d . . . H11 H 0.7079 0.3156 0.6474 0.048 Uiso 1 1 calc R . . C12 C 0.7956(3) 0.26117(9) 0.79025(17) 0.0412(5) Uani 1 1 d . . . H12 H 0.8377 0.2995 0.8356 0.049 Uiso 1 1 calc R . . C13 C 0.8098(2) 0.19602(9) 0.83597(16) 0.0350(4) Uani 1 1 d . . . H13 H 0.8600 0.1896 0.9131 0.042 Uiso 1 1 calc R . . C14 C 0.7509(2) 0.14000(8) 0.76933(15) 0.0283(4) Uani 1 1 d . . . C15 C 0.6561(2) 0.04543(9) 0.88954(14) 0.0286(4) Uani 1 1 d . . . O2 O 0.38160(19) 0.22041(7) 0.85796(11) 0.0434(4) Uani 1 1 d . . . N3 N 0.2753(3) 0.28582(14) 0.7060(2) 0.0346(7) Uani 0.720(4) 1 d P A 1 C16 C 0.3013(5) 0.2256(2) 0.7601(4) 0.0342(9) Uani 0.720(4) 1 d P A 1 C17 C 0.2137(5) 0.1699(2) 0.6843(3) 0.0455(9) Uani 0.720(4) 1 d P A 1 H17A H 0.1069 0.1518 0.7142 0.055 Uiso 0.720(4) 1 calc PR A 1 H17B H 0.2982 0.1317 0.6781 0.055 Uiso 0.720(4) 1 calc PR A 1 C18 C 0.1609(4) 0.2045(2) 0.5690(3) 0.0523(10) Uani 0.720(4) 1 d P A 1 H18A H 0.0380 0.1913 0.5358 0.063 Uiso 0.720(4) 1 calc PR A 1 H18B H 0.2445 0.1916 0.5153 0.063 Uiso 0.720(4) 1 calc PR A 1 C19 C 0.1717(5) 0.2814(2) 0.5944(3) 0.0423(10) Uani 0.720(4) 1 d P A 1 H19A H 0.2320 0.3060 0.5375 0.051 Uiso 0.720(4) 1 calc PR A 1 H19B H 0.0508 0.3011 0.5945 0.051 Uiso 0.720(4) 1 calc PR A 1 C20 C 0.3327(5) 0.35058(17) 0.7590(3) 0.0499(10) Uani 0.720(4) 1 d P A 1 H20A H 0.2287 0.3751 0.7800 0.075 Uiso 0.720(4) 1 calc PR A 1 H20B H 0.3896 0.3784 0.7054 0.075 Uiso 0.720(4) 1 calc PR A 1 H20C H 0.4186 0.3420 0.8273 0.075 Uiso 0.720(4) 1 calc PR A 1 N4 N 0.2293(8) 0.2147(4) 0.6792(6) 0.0358(18) Uiso 0.280(4) 1 d P A 2 C23 C 0.2006(15) 0.3278(7) 0.6194(9) 0.079(3) Uiso 0.280(4) 1 d P A 2 H23A H 0.2834 0.3489 0.5716 0.095 Uiso 0.280(4) 1 calc PR A 2 H23B H 0.0902 0.3558 0.6127 0.095 Uiso 0.280(4) 1 calc PR A 2 C25 C 0.2142(16) 0.1429(5) 0.6736(11) 0.051(3) Uiso 0.280(4) 1 d P A 2 H25A H 0.2852 0.1253 0.6168 0.076 Uiso 0.280(4) 1 calc PR A 2 H25B H 0.0884 0.1302 0.6519 0.076 Uiso 0.280(4) 1 calc PR A 2 H25C H 0.2584 0.1231 0.7480 0.076 Uiso 0.280(4) 1 calc PR A 2 C22 C 0.1555(17) 0.2543(6) 0.5797(11) 0.043(3) Uiso 0.280(4) 1 d P A 2 H22A H 0.0247 0.2475 0.5612 0.051 Uiso 0.280(4) 1 calc PR A 2 H22B H 0.2137 0.2423 0.5126 0.051 Uiso 0.280(4) 1 calc PR A 2 C24 C 0.2864(15) 0.3253(7) 0.7404(10) 0.048(3) Uiso 0.280(4) 1 d P A 2 H24A H 0.2100 0.3482 0.7904 0.058 Uiso 0.280(4) 1 calc PR A 2 H24B H 0.4046 0.3482 0.7495 0.058 Uiso 0.280(4) 1 calc PR A 2 C21 C 0.3067(15) 0.2498(5) 0.7693(11) 0.032(3) Uiso 0.280(4) 1 d P A 2 H2N H 0.507(2) 0.1287(10) 0.8953(16) 0.038(5) Uiso 1 1 d . . . H1N H 0.464(3) 0.0672(10) 0.9719(16) 0.044(6) 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 0.0416(7) 0.0219(7) 0.0401(7) 0.0056(6) 0.0119(6) 0.0022(5) N1 0.0377(9) 0.0204(8) 0.0346(8) 0.0045(6) 0.0126(7) 0.0036(6) N2 0.0402(10) 0.0246(9) 0.0406(10) 0.0088(7) 0.0153(8) 0.0067(7) C1 0.0368(10) 0.0177(9) 0.0371(10) 0.0036(7) 0.0123(8) -0.0009(7) C2 0.0424(11) 0.0263(10) 0.0351(10) 0.0043(8) 0.0089(9) 0.0009(8) C3 0.0385(11) 0.0292(10) 0.0434(12) 0.0084(9) 0.0068(9) 0.0046(8) C4 0.0463(12) 0.0223(10) 0.0493(12) 0.0035(9) 0.0174(10) 0.0061(8) C5 0.0477(12) 0.0230(9) 0.0378(11) -0.0025(8) 0.0116(9) -0.0023(8) C6 0.0372(10) 0.0209(9) 0.0359(10) 0.0007(8) 0.0094(8) -0.0033(8) C7 0.0389(11) 0.0297(10) 0.0401(11) -0.0071(8) 0.0056(9) -0.0067(8) C8 0.0328(10) 0.0366(11) 0.0356(11) 0.0003(8) 0.0020(8) -0.0017(8) C9 0.0295(10) 0.0275(9) 0.0346(10) 0.0018(8) 0.0091(8) -0.0002(7) C10 0.0356(10) 0.0334(11) 0.0378(10) 0.0110(9) 0.0102(8) 0.0050(8) C11 0.0446(12) 0.0214(10) 0.0578(13) 0.0091(9) 0.0164(10) 0.0032(8) C12 0.0501(13) 0.0230(10) 0.0515(13) -0.0037(9) 0.0109(10) -0.0034(9) C13 0.0412(11) 0.0266(10) 0.0373(10) -0.0019(8) 0.0066(8) 0.0001(8) C14 0.0300(10) 0.0210(9) 0.0353(10) 0.0031(8) 0.0100(8) 0.0020(7) C15 0.0333(10) 0.0243(9) 0.0277(9) 0.0017(7) 0.0026(8) 0.0001(8) O2 0.0549(9) 0.0391(8) 0.0366(8) 0.0054(6) 0.0083(7) 0.0111(7) N3 0.0423(14) 0.0261(15) 0.0362(14) 0.0042(12) 0.0080(10) 0.0061(10) C16 0.0370(19) 0.026(2) 0.043(2) 0.0017(18) 0.0175(15) 0.0061(16) C17 0.0409(19) 0.038(3) 0.060(2) -0.006(2) 0.0172(15) -0.0050(17) C18 0.0461(18) 0.061(3) 0.0491(19) -0.0122(17) 0.0052(14) -0.0038(16) C19 0.045(2) 0.047(3) 0.0337(19) 0.0031(19) 0.0032(14) 0.0054(19) C20 0.059(2) 0.028(2) 0.064(2) 0.0004(17) 0.0138(18) 0.0089(17) 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 C15 1.2368(19) . ? N1 C15 1.382(2) . ? N1 C14 1.433(2) . ? N1 C1 1.438(2) . ? N2 C15 1.340(2) . ? N2 H2N 0.89(2) . ? N2 H1N 0.92(2) . ? C1 C2 1.382(3) . ? C1 C6 1.393(2) . ? C2 C3 1.383(3) . ? C2 H2 0.9500 . ? C3 C4 1.384(3) . ? C3 H3 0.9500 . ? C4 C5 1.377(3) . ? C4 H4 0.9500 . ? C5 C6 1.407(3) . ? C5 H5 0.9500 . ? C6 C7 1.459(3) . ? C7 C8 1.342(2) . ? C7 H7 0.9500 . ? C8 C9 1.462(2) . ? C8 H8 0.9500 . ? C9 C14 1.399(3) . ? C9 C10 1.406(2) . ? C10 C11 1.380(3) . ? C10 H10 0.9500 . ? C11 C12 1.385(3) . ? C11 H11 0.9500 . ? C12 C13 1.381(3) . ? C12 H12 0.9500 . ? C13 C14 1.386(2) . ? C13 H13 0.9500 . ? O2 C16 1.238(4) . ? O2 C21 1.262(13) . ? N3 C16 1.339(4) . ? N3 C19 1.445(4) . ? N3 C20 1.451(4) . ? C16 C17 1.505(6) . ? C17 C18 1.530(5) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.531(5) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? N4 C21 1.335(13) . ? N4 C25 1.406(11) . ? N4 C22 1.457(14) . ? C23 C24 1.493(15) . ? C23 C22 1.533(14) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C24 C21 1.515(15) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? 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 C14 125.03(14) . . ? C15 N1 C1 119.49(14) . . ? C14 N1 C1 115.29(13) . . ? C15 N2 H2N 123.8(12) . . ? C15 N2 H1N 114.3(12) . . ? H2N N2 H1N 120.1(17) . . ? C2 C1 C6 121.60(16) . . ? C2 C1 N1 119.72(16) . . ? C6 C1 N1 118.66(16) . . ? C1 C2 C3 119.97(17) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C2 C3 C4 119.51(18) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 120.62(18) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.79(17) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 117.42(17) . . ? C1 C6 C7 122.93(16) . . ? C5 C6 C7 119.56(17) . . ? C8 C7 C6 126.95(17) . . ? C8 C7 H7 116.5 . . ? C6 C7 H7 116.5 . . ? C7 C8 C9 127.13(17) . . ? C7 C8 H8 116.4 . . ? C9 C8 H8 116.4 . . ? C14 C9 C10 117.91(16) . . ? C14 C9 C8 122.40(16) . . ? C10 C9 C8 119.64(16) . . ? C11 C10 C9 120.68(17) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.30(17) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 120.01(18) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 120.02(18) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C9 120.97(16) . . ? C13 C14 N1 120.00(16) . . ? C9 C14 N1 119.01(15) . . ? O1 C15 N2 123.04(16) . . ? O1 C15 N1 119.56(15) . . ? N2 C15 N1 117.39(15) . . ? C16 O2 C21 22.3(4) . . ? C16 N3 C19 114.4(3) . . ? C16 N3 C20 122.7(3) . . ? C19 N3 C20 122.7(3) . . ? O2 C16 N3 122.8(4) . . ? O2 C16 C17 128.2(3) . . ? N3 C16 C17 108.9(4) . . ? C16 C17 C18 104.7(3) . . ? C16 C17 H17A 110.8 . . ? C18 C17 H17A 110.8 . . ? C16 C17 H17B 110.8 . . ? C18 C17 H17B 110.8 . . ? H17A C17 H17B 108.9 . . ? C17 C18 C19 104.9(3) . . ? C17 C18 H18A 110.8 . . ? C19 C18 H18A 110.8 . . ? C17 C18 H18B 110.8 . . ? C19 C18 H18B 110.8 . . ? H18A C18 H18B 108.8 . . ? N3 C19 C18 104.2(3) . . ? N3 C19 H19A 110.9 . . ? C18 C19 H19A 110.9 . . ? N3 C19 H19B 110.9 . . ? C18 C19 H19B 110.9 . . ? H19A C19 H19B 108.9 . . ? C21 N4 C25 125.0(9) . . ? C21 N4 C22 116.9(9) . . ? C25 N4 C22 118.1(9) . . ? C24 C23 C22 108.3(11) . . ? C24 C23 H23A 110.0 . . ? C22 C23 H23A 110.0 . . ? C24 C23 H23B 110.0 . . ? C22 C23 H23B 110.0 . . ? H23A C23 H23B 108.4 . . ? N4 C25 H25A 109.5 . . ? N4 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N4 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N4 C22 C23 101.8(9) . . ? N4 C22 H22A 111.4 . . ? C23 C22 H22A 111.4 . . ? N4 C22 H22B 111.4 . . ? C23 C22 H22B 111.4 . . ? H22A C22 H22B 109.3 . . ? C23 C24 C21 105.4(11) . . ? C23 C24 H24A 110.7 . . ? C21 C24 H24A 110.7 . . ? C23 C24 H24B 110.7 . . ? C21 C24 H24B 110.7 . . ? H24A C24 H24B 108.8 . . ? O2 C21 N4 122.0(9) . . ? O2 C21 C24 130.6(9) . . ? N4 C21 C24 107.4(11) . . ? 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 C15 N1 C1 C2 -75.6(2) . . . . ? C14 N1 C1 C2 109.16(18) . . . . ? C15 N1 C1 C6 105.67(19) . . . . ? C14 N1 C1 C6 -69.6(2) . . . . ? C6 C1 C2 C3 -0.9(3) . . . . ? N1 C1 C2 C3 -179.57(15) . . . . ? C1 C2 C3 C4 -1.1(3) . . . . ? C2 C3 C4 C5 0.9(3) . . . . ? C3 C4 C5 C6 1.4(3) . . . . ? C2 C1 C6 C5 3.1(3) . . . . ? N1 C1 C6 C5 -178.24(15) . . . . ? C2 C1 C6 C7 -173.53(16) . . . . ? N1 C1 C6 C7 5.2(2) . . . . ? C4 C5 C6 C1 -3.3(3) . . . . ? C4 C5 C6 C7 173.40(16) . . . . ? C1 C6 C7 C8 32.4(3) . . . . ? C5 C6 C7 C8 -144.09(19) . . . . ? C6 C7 C8 C9 -0.2(3) . . . . ? C7 C8 C9 C14 -32.4(3) . . . . ? C7 C8 C9 C10 144.84(19) . . . . ? C14 C9 C10 C11 3.2(3) . . . . ? C8 C9 C10 C11 -174.12(16) . . . . ? C9 C10 C11 C12 -0.7(3) . . . . ? C10 C11 C12 C13 -1.4(3) . . . . ? C11 C12 C13 C14 0.9(3) . . . . ? C12 C13 C14 C9 1.7(3) . . . . ? C12 C13 C14 N1 179.88(16) . . . . ? C10 C9 C14 C13 -3.7(3) . . . . ? C8 C9 C14 C13 173.56(16) . . . . ? C10 C9 C14 N1 178.07(15) . . . . ? C8 C9 C14 N1 -4.7(2) . . . . ? C15 N1 C14 C13 76.0(2) . . . . ? C1 N1 C14 C13 -109.08(18) . . . . ? C15 N1 C14 C9 -105.76(19) . . . . ? C1 N1 C14 C9 69.2(2) . . . . ? C14 N1 C15 O1 175.36(16) . . . . ? C1 N1 C15 O1 0.6(2) . . . . ? C14 N1 C15 N2 -5.9(2) . . . . ? C1 N1 C15 N2 179.42(15) . . . . ? C21 O2 C16 N3 8.4(14) . . . . ? C21 O2 C16 C17 -169.5(18) . . . . ? C19 N3 C16 O2 -177.4(3) . . . . ? C20 N3 C16 O2 -2.5(4) . . . . ? C19 N3 C16 C17 0.9(4) . . . . ? C20 N3 C16 C17 175.7(3) . . . . ? O2 C16 C17 C18 -172.0(3) . . . . ? N3 C16 C17 C18 9.9(3) . . . . ? C16 C17 C18 C19 -16.0(3) . . . . ? C16 N3 C19 C18 -11.2(3) . . . . ? C20 N3 C19 C18 173.9(3) . . . . ? C17 C18 C19 N3 16.3(3) . . . . ? C21 N4 C22 C23 0.6(12) . . . . ? C25 N4 C22 C23 -179.3(9) . . . . ? C24 C23 C22 N4 -3.4(12) . . . . ? C22 C23 C24 C21 4.8(13) . . . . ? C16 O2 C21 N4 2.5(8) . . . . ? C16 O2 C21 C24 -177(3) . . . . ? C25 N4 C21 O2 3.1(15) . . . . ? C22 N4 C21 O2 -176.9(9) . . . . ? C25 N4 C21 C24 -177.7(9) . . . . ? C22 N4 C21 C24 2.4(12) . . . . ? C23 C24 C21 O2 174.8(10) . . . . ? C23 C24 C21 N4 -4.4(12) . . . . ? _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. ; _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. ; _computing_data_collection 'Denzo & Collect' _computing_structure_solution SIR _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' # Attachment 'Nome-CSD-extras.cif' data_CBZNOme _database_code_depnum_ccdc_archive 'CCDC 643266' _chemical_name_systematic ; [5H-dibenz(b,f)azepine-5-carboxamide]nitromethane solvate ; _chemical_name_common '(5H-dibenz(b,f)azepine-5-carboxamide)nitromethane solvate' _chemical_formula_sum 'C16 H15 N3 O3' _chemical_formula_weight 297.31 _exptl_crystal_colour colourless _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_preparation ; recyrstallised by slow evaporation from nitromethane at 278 K. ; _cell_length_a 10.9242(11) _cell_length_b 5.1617(5) _cell_length_c 26.309(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.104(2) _cell_angle_gamma 90.00 _cell_volume 1460.5(3) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n 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' _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3185 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 26.02 _exptl_crystal_density_diffrn 1.352 _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_special_details ; Crystals shatter on introduction to cold stream. Data collected from fragment left by larger crystal. ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 15958 _diffrn_reflns_av_R_equivalents 0.088 _diffrn_reflns_av_sigmaI/netI 0.0760 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 26.05 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.210 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.046 _audit_creation_method SHELXL-97 _reflns_number_total 2888 _reflns_number_gt 1707 _reflns_threshold_expression I>2\s(I) _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^)+(0.0363P)^2^+0.4225P] 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 2888 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1119 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1083 _refine_ls_wR_factor_gt 0.0902 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.001 _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 1.06693(14) 0.1622(3) 0.94598(6) 0.0311(4) Uani 1 1 d . . . O2 O 1.36445(16) -0.0632(4) 1.00149(8) 0.0471(5) Uani 1 1 d . . . O3 O 1.34919(17) -0.0534(4) 0.91844(8) 0.0614(6) Uani 1 1 d . . . N1 N 0.91320(16) 0.3767(4) 0.89270(6) 0.0234(5) Uani 1 1 d . . . N2 N 0.8774(2) 0.1928(5) 0.96892(8) 0.0321(5) Uani 1 1 d . . . N3 N 1.35277(17) 0.0525(4) 0.95996(9) 0.0361(5) Uani 1 1 d . . . C1 C 0.7824(2) 0.4253(4) 0.87710(8) 0.0242(5) Uani 1 1 d . . . C2 C 0.7279(2) 0.6235(5) 0.90067(9) 0.0299(6) Uani 1 1 d . . . H2 H 0.7778 0.7363 0.9242 0.036 Uiso 1 1 calc R . . C3 C 0.5996(2) 0.6568(5) 0.88969(9) 0.0353(6) Uani 1 1 d . . . H3 H 0.5616 0.7920 0.9059 0.042 Uiso 1 1 calc R . . C4 C 0.5280(2) 0.4938(5) 0.85542(9) 0.0371(7) Uani 1 1 d . . . H4 H 0.4403 0.5141 0.8486 0.045 Uiso 1 1 calc R . . C5 C 0.5825(2) 0.3013(5) 0.83092(9) 0.0327(6) Uani 1 1 d . . . H5 H 0.5315 0.1908 0.8072 0.039 Uiso 1 1 calc R . . C6 C 0.7118(2) 0.2648(5) 0.84017(8) 0.0266(6) Uani 1 1 d . . . C7 C 0.7668(2) 0.0660(5) 0.81165(9) 0.0300(6) Uani 1 1 d . . . C8 C 0.8807(2) 0.0656(5) 0.79937(9) 0.0287(6) Uani 1 1 d . . . C9 C 0.9781(2) 0.2611(4) 0.81120(8) 0.0248(5) Uani 1 1 d . . . C10 C 1.0611(2) 0.3003(5) 0.77684(9) 0.0307(6) Uani 1 1 d . . . H10 H 1.0557 0.1925 0.7473 0.037 Uiso 1 1 calc R . . C11 C 1.1505(2) 0.4922(5) 0.78503(9) 0.0315(6) Uani 1 1 d . . . H11 H 1.2056 0.5157 0.7612 0.038 Uiso 1 1 calc R . . C12 C 1.1598(2) 0.6500(5) 0.82797(9) 0.0296(6) Uani 1 1 d . . . H12 H 1.2203 0.7840 0.8333 0.035 Uiso 1 1 calc R . . C13 C 1.0808(2) 0.6129(5) 0.86325(8) 0.0268(6) Uani 1 1 d . . . H13 H 1.0875 0.7204 0.8929 0.032 Uiso 1 1 calc R . . C14 C 0.9921(2) 0.4189(5) 0.85510(8) 0.0239(5) Uani 1 1 d . . . C15 C 0.9578(2) 0.2377(4) 0.93688(8) 0.0247(5) Uani 1 1 d . . . C16 C 1.3430(2) 0.3368(5) 0.96082(10) 0.0354(6) Uani 1 1 d . . . H16A H 1.3471 0.3958 0.9965 0.053 Uiso 0.50 1 calc PR . . H16B H 1.2637 0.3906 0.9401 0.053 Uiso 0.50 1 calc PR . . H16C H 1.4117 0.4133 0.9465 0.053 Uiso 0.50 1 calc PR . . H16D H 1.3345 0.4040 0.9255 0.053 Uiso 0.50 1 calc PR . . H16E H 1.4180 0.4092 0.9820 0.053 Uiso 0.50 1 calc PR . . H16F H 1.2700 0.3865 0.9755 0.053 Uiso 0.50 1 calc PR . . H8 H 0.9000(18) -0.078(4) 0.7778(8) 0.021(6) Uiso 1 1 d . . . H1N H 0.801(2) 0.227(5) 0.9599(9) 0.036(8) Uiso 1 1 d . . . H7 H 0.712(2) -0.078(5) 0.7975(9) 0.040(7) Uiso 1 1 d . . . H2N H 0.902(3) 0.084(6) 0.9968(11) 0.065(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 0.0226(9) 0.0403(11) 0.0305(9) 0.0080(8) 0.0050(7) 0.0038(8) O2 0.0362(11) 0.0391(12) 0.0691(14) 0.0138(11) 0.0175(10) -0.0001(9) O3 0.0474(12) 0.0719(16) 0.0638(14) -0.0377(12) 0.0069(10) 0.0042(11) N1 0.0192(10) 0.0285(12) 0.0231(10) 0.0030(9) 0.0051(8) 0.0026(9) N2 0.0234(12) 0.0425(15) 0.0314(12) 0.0128(11) 0.0081(10) 0.0058(11) N3 0.0222(11) 0.0382(15) 0.0494(14) -0.0084(13) 0.0101(10) -0.0028(10) C1 0.0226(12) 0.0269(14) 0.0247(12) 0.0053(11) 0.0087(10) 0.0008(11) C2 0.0326(14) 0.0281(15) 0.0314(13) 0.0033(11) 0.0118(11) 0.0025(12) C3 0.0331(14) 0.0408(17) 0.0349(14) 0.0088(13) 0.0142(12) 0.0119(13) C4 0.0238(13) 0.0545(19) 0.0339(14) 0.0150(14) 0.0072(12) 0.0077(14) C5 0.0263(13) 0.0448(17) 0.0265(12) 0.0085(12) 0.0031(11) -0.0037(13) C6 0.0248(12) 0.0296(15) 0.0257(12) 0.0063(11) 0.0056(10) 0.0003(12) C7 0.0324(14) 0.0273(16) 0.0294(13) 0.0004(12) 0.0030(11) -0.0053(13) C8 0.0343(14) 0.0260(15) 0.0259(13) -0.0007(12) 0.0060(11) 0.0009(12) C9 0.0248(12) 0.0240(14) 0.0259(12) 0.0032(11) 0.0054(10) 0.0036(11) C10 0.0303(13) 0.0352(16) 0.0272(13) -0.0023(11) 0.0067(11) 0.0009(12) C11 0.0276(13) 0.0392(16) 0.0299(13) 0.0042(12) 0.0110(11) 0.0016(13) C12 0.0226(12) 0.0326(16) 0.0333(13) 0.0057(12) 0.0043(11) -0.0030(11) C13 0.0262(13) 0.0264(14) 0.0275(12) 0.0013(11) 0.0035(11) 0.0017(11) C14 0.0216(12) 0.0273(14) 0.0234(12) 0.0047(11) 0.0057(10) 0.0060(11) C15 0.0257(13) 0.0235(14) 0.0248(12) -0.0006(11) 0.0046(10) -0.0024(11) C16 0.0354(15) 0.0256(16) 0.0465(15) 0.0033(12) 0.0108(12) -0.0004(12) 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 C15 1.237(2) . ? O2 N3 1.232(3) . ? O3 N3 1.216(2) . ? N1 C15 1.380(3) . ? N1 C1 1.438(3) . ? N1 C14 1.438(3) . ? N2 C15 1.340(3) . ? N2 H1N 0.84(2) . ? N2 H2N 0.92(3) . ? N3 C16 1.472(3) . ? C1 C2 1.384(3) . ? C1 C6 1.401(3) . ? C2 C3 1.391(3) . ? C2 H2 0.9500 . ? C3 C4 1.373(4) . ? C3 H3 0.9500 . ? C4 C5 1.375(3) . ? C4 H4 0.9500 . ? C5 C6 1.403(3) . ? C5 H5 0.9500 . ? C6 C7 1.461(3) . ? C7 C8 1.340(3) . ? C7 H7 0.99(3) . ? C8 C9 1.460(3) . ? C8 H8 0.98(2) . ? C9 C14 1.400(3) . ? C9 C10 1.403(3) . ? C10 C11 1.382(3) . ? C10 H10 0.9500 . ? C11 C12 1.382(3) . ? C11 H11 0.9500 . ? C12 C13 1.387(3) . ? C12 H12 0.9500 . ? C13 C14 1.384(3) . ? C13 H13 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C16 H16D 0.9800 . ? C16 H16E 0.9800 . ? C16 H16F 0.9800 . ? 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 C1 121.16(17) . . ? C15 N1 C14 119.53(17) . . ? C1 N1 C14 117.55(17) . . ? C15 N2 H1N 120.7(16) . . ? C15 N2 H2N 118.3(17) . . ? H1N N2 H2N 119(2) . . ? O3 N3 O2 124.1(2) . . ? O3 N3 C16 118.1(2) . . ? O2 N3 C16 117.8(2) . . ? C2 C1 C6 121.3(2) . . ? C2 C1 N1 119.0(2) . . ? C6 C1 N1 119.6(2) . . ? C1 C2 C3 119.7(2) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 119.8(2) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.5(2) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 121.4(2) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 117.1(2) . . ? C1 C6 C7 123.1(2) . . ? C5 C6 C7 119.8(2) . . ? C8 C7 C6 127.5(3) . . ? C8 C7 H7 115.9(13) . . ? C6 C7 H7 116.5(13) . . ? C7 C8 C9 128.4(2) . . ? C7 C8 H8 116.3(12) . . ? C9 C8 H8 115.2(12) . . ? C14 C9 C10 117.3(2) . . ? C14 C9 C8 123.3(2) . . ? C10 C9 C8 119.4(2) . . ? C11 C10 C9 121.5(2) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C12 119.9(2) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C11 C12 C13 120.1(2) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C14 C13 C12 119.8(2) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C9 121.4(2) . . ? C13 C14 N1 119.4(2) . . ? C9 C14 N1 119.2(2) . . ? O1 C15 N2 122.6(2) . . ? O1 C15 N1 120.84(19) . . ? N2 C15 N1 116.5(2) . . ? N3 C16 H16A 109.5 . . ? N3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N3 C16 H16D 109.5 . . ? H16A C16 H16D 141.1 . . ? H16B C16 H16D 56.3 . . ? H16C C16 H16D 56.3 . . ? N3 C16 H16E 109.5 . . ? H16A C16 H16E 56.3 . . ? H16B C16 H16E 141.1 . . ? H16C C16 H16E 56.3 . . ? H16D C16 H16E 109.5 . . ? N3 C16 H16F 109.5 . . ? H16A C16 H16F 56.3 . . ? H16B C16 H16F 56.3 . . ? H16C C16 H16F 141.1 . . ? H16D C16 H16F 109.5 . . ? H16E C16 H16F 109.5 . . ? 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 C15 N1 C1 C2 80.1(3) . . . . ? C14 N1 C1 C2 -115.1(2) . . . . ? C15 N1 C1 C6 -97.1(2) . . . . ? C14 N1 C1 C6 67.7(3) . . . . ? C6 C1 C2 C3 3.4(3) . . . . ? N1 C1 C2 C3 -173.7(2) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C2 C3 C4 C5 -1.5(4) . . . . ? C3 C4 C5 C6 0.2(4) . . . . ? C2 C1 C6 C5 -4.5(3) . . . . ? N1 C1 C6 C5 172.58(19) . . . . ? C2 C1 C6 C7 175.4(2) . . . . ? N1 C1 C6 C7 -7.5(3) . . . . ? C4 C5 C6 C1 2.7(3) . . . . ? C4 C5 C6 C7 -177.2(2) . . . . ? C1 C6 C7 C8 -28.4(4) . . . . ? C5 C6 C7 C8 151.5(2) . . . . ? C6 C7 C8 C9 0.0(4) . . . . ? C7 C8 C9 C14 29.9(4) . . . . ? C7 C8 C9 C10 -148.6(2) . . . . ? C14 C9 C10 C11 -2.0(3) . . . . ? C8 C9 C10 C11 176.6(2) . . . . ? C9 C10 C11 C12 0.2(4) . . . . ? C10 C11 C12 C13 1.1(4) . . . . ? C11 C12 C13 C14 -0.5(3) . . . . ? C12 C13 C14 C9 -1.4(3) . . . . ? C12 C13 C14 N1 178.0(2) . . . . ? C10 C9 C14 C13 2.6(3) . . . . ? C8 C9 C14 C13 -175.9(2) . . . . ? C10 C9 C14 N1 -176.8(2) . . . . ? C8 C9 C14 N1 4.6(3) . . . . ? C15 N1 C14 C13 -80.1(3) . . . . ? C1 N1 C14 C13 114.9(2) . . . . ? C15 N1 C14 C9 99.4(2) . . . . ? C1 N1 C14 C9 -65.7(3) . . . . ? C1 N1 C15 O1 168.8(2) . . . . ? C14 N1 C15 O1 4.3(3) . . . . ? C1 N1 C15 N2 -11.8(3) . . . . ? C14 N1 C15 N2 -176.3(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. ; _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. ; _computing_data_collection 'Collect and Denzo' _computing_structure_solution SIR _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'