#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202120.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_2202120 loop_ _publ_author_name 'Xiangshan Wang' 'Daqing Shi' 'Shujiang Tu' 'Kaibei Yu' _publ_section_title ; 2-Amino-4-phenyl-5,6-dihydrobenzo[h]quinazoline ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o423 _journal_page_last o424 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C18 H15 N3' _chemical_formula_moiety 'C18 H15 N3' _chemical_formula_sum 'C18 H15 N3' _chemical_formula_weight 273.33 _chemical_melting_point 447.5(5) _chemical_name_systematic ; 2-amino-4-phenyl-5,6-dihydrobenzo[h]quinazoline ; _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 _cell_angle_alpha 90.00 _cell_angle_beta 94.850(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.902(2) _cell_length_b 6.9060(10) _cell_length_c 18.577(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 12.58 _cell_measurement_theta_min 3.01 _cell_volume 1393.6(4) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1994)' _computing_data_reduction 'SHELXTL (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution SHELXTL _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 2919 _diffrn_reflns_theta_full 24.99 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 1.87 _diffrn_standards_decay_% 0.97 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 576 _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_min 0.24 _refine_diff_density_max 0.148 _refine_diff_density_min -0.180 _refine_ls_extinction_coef 0.043(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXTL _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 199 _refine_ls_number_reflns 2448 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.015 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0376 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0602P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0973 _refine_ls_wR_factor_ref 0.1023 _reflns_number_gt 1810 _reflns_number_total 2448 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ob6223.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '447-448' was changed to '447.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '447-448' was changed to '447.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2202120 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_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 _atom_site_type_symbol N1 0.81730(11) 0.17629(17) 0.71624(6) 0.0400(3) Uani d . 1 . . N N2 0.89605(10) 0.45988(18) 0.66146(6) 0.0394(3) Uani d . 1 . . N N3 0.98173(14) 0.3452(2) 0.77085(8) 0.0564(4) Uani d D 1 . . N C1 0.89514(13) 0.3265(2) 0.71412(8) 0.0386(4) Uani d . 1 . . C C2 0.72585(12) 0.1698(2) 0.66278(7) 0.0362(4) Uani d . 1 . . C C3 0.63317(13) 0.0136(2) 0.66516(7) 0.0382(4) Uani d . 1 . . C C4 0.65687(15) -0.1548(2) 0.70558(8) 0.0457(4) Uani d . 1 . . C H4 0.7331 -0.1717 0.7313 0.055 Uiso calc R 1 . . H C5 0.56794(17) -0.2965(2) 0.70770(9) 0.0545(5) Uani d . 1 . . C H5 0.5850 -0.4098 0.7337 0.065 Uiso calc R 1 . . H C6 0.45352(17) -0.2697(3) 0.67108(9) 0.0554(5) Uani d . 1 . . C H6 0.3929 -0.3637 0.6733 0.066 Uiso calc R 1 . . H C7 0.42935(15) -0.1043(3) 0.63135(8) 0.0493(4) Uani d . 1 . . C H7 0.3518 -0.0873 0.6072 0.059 Uiso calc R 1 . . H C8 0.51843(13) 0.0382(2) 0.62648(8) 0.0410(4) Uani d . 1 . . C C9 0.49366(14) 0.2206(3) 0.58360(9) 0.0522(5) Uani d . 1 . . C H9A 0.4671 0.3217 0.6150 0.063 Uiso calc R 1 . . H H9B 0.4279 0.1978 0.5460 0.063 Uiso calc R 1 . . H C10 0.60837(15) 0.2862(3) 0.54961(8) 0.0506(4) Uani d . 1 . . C H10A 0.6276 0.1942 0.5127 0.061 Uiso calc R 1 . . H H10B 0.5933 0.4111 0.5267 0.061 Uiso calc R 1 . . H C11 0.71635(13) 0.3018(2) 0.60602(8) 0.0371(4) Uani d . 1 . . C C12 0.80931(12) 0.4404(2) 0.60587(7) 0.0364(4) Uani d . 1 . . C C13 0.82260(13) 0.5716(2) 0.54317(8) 0.0397(4) Uani d . 1 . . C C14 0.84315(14) 0.7687(2) 0.55284(9) 0.0474(4) Uani d . 1 . . C H14 0.8449 0.8221 0.5989 0.057 Uiso calc R 1 . . H C15 0.86105(15) 0.8857(3) 0.49434(11) 0.0599(5) Uani d . 1 . . C H15 0.8733 1.0179 0.5012 0.072 Uiso calc R 1 . . H C16 0.86099(16) 0.8083(3) 0.42585(11) 0.0657(6) Uani d . 1 . . C H16 0.8744 0.8875 0.3868 0.079 Uiso calc R 1 . . H C17 0.84098(15) 0.6137(3) 0.41569(10) 0.0624(5) Uani d . 1 . . C H17 0.8409 0.5609 0.3696 0.075 Uiso calc R 1 . . H C18 0.82096(14) 0.4958(3) 0.47366(8) 0.0509(4) Uani d . 1 . . C H18 0.8062 0.3644 0.4661 0.061 Uiso calc R 1 . . H H3A 0.9949(16) 0.2419(19) 0.7981(8) 0.061(5) Uiso d D 1 . . H H3B 1.0409(13) 0.430(2) 0.7671(10) 0.069(6) Uiso d D 1 . . H 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 N1 0.0399(7) 0.0390(7) 0.0396(7) -0.0008(6) -0.0051(6) 0.0016(6) N2 0.0369(7) 0.0391(7) 0.0411(7) 0.0003(5) -0.0036(5) 0.0011(6) N3 0.0581(10) 0.0503(9) 0.0560(9) -0.0122(8) -0.0230(8) 0.0111(8) C1 0.0369(8) 0.0371(8) 0.0403(8) 0.0012(7) -0.0051(7) -0.0014(7) C2 0.0350(8) 0.0377(8) 0.0355(8) 0.0029(6) 0.0011(6) -0.0025(6) C3 0.0414(8) 0.0401(9) 0.0334(7) -0.0026(7) 0.0052(6) -0.0036(7) C4 0.0504(10) 0.0456(10) 0.0413(9) -0.0026(8) 0.0054(7) 0.0029(7) C5 0.0724(12) 0.0439(10) 0.0483(10) -0.0095(9) 0.0115(9) 0.0041(8) C6 0.0619(11) 0.0535(11) 0.0518(10) -0.0221(9) 0.0104(8) -0.0061(9) C7 0.0448(9) 0.0581(11) 0.0449(9) -0.0111(8) 0.0036(7) -0.0085(8) C8 0.0407(8) 0.0453(9) 0.0370(8) -0.0042(7) 0.0039(6) -0.0073(7) C9 0.0392(9) 0.0560(11) 0.0590(10) -0.0046(8) -0.0103(8) 0.0031(9) C10 0.0466(9) 0.0557(10) 0.0473(9) -0.0079(8) -0.0096(7) 0.0108(8) C11 0.0345(8) 0.0387(8) 0.0374(8) 0.0000(7) -0.0007(6) 0.0002(7) C12 0.0353(8) 0.0350(8) 0.0387(8) 0.0039(6) 0.0013(6) -0.0001(6) C13 0.0308(8) 0.0452(9) 0.0426(9) 0.0013(7) -0.0004(6) 0.0061(7) C14 0.0410(9) 0.0456(10) 0.0546(10) -0.0010(7) -0.0009(7) 0.0059(8) C15 0.0467(10) 0.0495(10) 0.0836(14) -0.0020(8) 0.0064(9) 0.0214(10) C16 0.0471(11) 0.0805(15) 0.0706(13) 0.0016(10) 0.0123(9) 0.0361(11) C17 0.0540(11) 0.0865(15) 0.0478(10) 0.0040(10) 0.0096(8) 0.0133(10) C18 0.0500(10) 0.0549(10) 0.0477(9) 0.0008(8) 0.0049(7) 0.0039(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C1 . 1.3431(19) yes N1 C2 . 1.3471(17) yes N2 C1 . 1.3442(18) yes N2 C12 . 1.3469(17) yes N3 C1 . 1.3603(19) yes N3 H3A . 0.880(9) no N3 H3B . 0.876(9) no C2 C11 . 1.392(2) yes C2 C3 . 1.481(2) no C3 C4 . 1.397(2) no C3 C8 . 1.399(2) no C4 C5 . 1.380(2) no C4 H4 . 0.9300 no C5 C6 . 1.382(2) no C5 H5 . 0.9300 no C6 C7 . 1.373(2) no C6 H6 . 0.9300 no C7 C8 . 1.391(2) no C7 H7 . 0.9300 no C8 C9 . 1.503(2) no C9 C10 . 1.517(2) yes C9 H9A . 0.9700 no C9 H9B . 0.9700 no C10 C11 . 1.512(2) no C10 H10A . 0.9700 no C10 H10B . 0.9700 no C11 C12 . 1.394(2) yes C12 C13 . 1.492(2) no C13 C14 . 1.389(2) no C13 C18 . 1.392(2) no C14 C15 . 1.381(2) no C14 H14 . 0.9300 no C15 C16 . 1.380(3) no C15 H15 . 0.9300 no C16 C17 . 1.372(3) no C16 H16 . 0.9300 no C17 C18 . 1.382(2) no C17 H17 . 0.9300 no C18 H18 . 0.9300 no 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 115.74(12) yes C1 N2 C12 116.21(12) yes C1 N3 H3A 116.0(12) no C1 N3 H3B 118.0(12) no H3A N3 H3B 119.9(17) no N1 C1 N2 126.45(12) yes N1 C1 N3 116.72(13) yes N2 C1 N3 116.83(14) yes N1 C2 C11 122.67(13) yes N1 C2 C3 117.81(12) yes C11 C2 C3 119.52(13) no C4 C3 C8 119.60(14) no C4 C3 C2 121.79(13) no C8 C3 C2 118.60(13) no C5 C4 C3 120.48(15) no C5 C4 H4 119.8 no C3 C4 H4 119.8 no C4 C5 C6 119.86(16) no C4 C5 H5 120.1 no C6 C5 H5 120.1 no C7 C6 C5 120.01(16) no C7 C6 H6 120.0 no C5 C6 H6 120.0 no C6 C7 C8 121.35(15) no C6 C7 H7 119.3 no C8 C7 H7 119.3 no C7 C8 C3 118.63(15) no C7 C8 C9 122.18(14) no C3 C8 C9 119.14(13) no C8 C9 C10 110.69(13) no C8 C9 H9A 109.5 no C10 C9 H9A 109.5 no C8 C9 H9B 109.5 no C10 C9 H9B 109.5 no H9A C9 H9B 108.1 no C11 C10 C9 110.71(13) no C11 C10 H10A 109.5 no C9 C10 H10A 109.5 no C11 C10 H10B 109.5 no C9 C10 H10B 109.5 no H10A C10 H10B 108.1 no C2 C11 C12 116.35(13) no C2 C11 C10 118.82(13) no C12 C11 C10 124.83(13) no N2 C12 C11 122.05(13) yes N2 C12 C13 115.43(13) yes C11 C12 C13 122.48(12) no C14 C13 C18 118.54(15) no C14 C13 C12 121.31(14) no C18 C13 C12 120.07(14) no C15 C14 C13 120.24(17) no C15 C14 H14 119.9 no C13 C14 H14 119.9 no C16 C15 C14 120.64(18) no C16 C15 H15 119.7 no C14 C15 H15 119.7 no C17 C16 C15 119.61(17) no C17 C16 H16 120.2 no C15 C16 H16 120.2 no C16 C17 C18 120.24(19) no C16 C17 H17 119.9 no C18 C17 H17 119.9 no C17 C18 C13 120.71(17) no C17 C18 H18 119.6 no C13 C18 H18 119.6 no 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 N3 H3B N1 2_756 0.876(9) 2.304(10) 3.162(2) 166.2(17) N3 H3A N2 2_746 0.880(9) 2.370(12) 3.1868(19) 154.4(15) 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_publ_flag C2 N1 C1 N2 -5.6(2) no C2 N1 C1 N3 174.53(13) no C12 N2 C1 N1 0.6(2) no C12 N2 C1 N3 -179.57(13) no C1 N1 C2 C11 4.2(2) no C1 N1 C2 C3 -176.37(12) no N1 C2 C3 C4 -20.1(2) no C11 C2 C3 C4 159.39(13) no N1 C2 C3 C8 158.98(13) no C11 C2 C3 C8 -21.5(2) yes C8 C3 C4 C5 -0.1(2) no C2 C3 C4 C5 178.94(13) no C3 C4 C5 C6 -1.6(2) no C4 C5 C6 C7 1.5(2) no C5 C6 C7 C8 0.5(2) no C6 C7 C8 C3 -2.2(2) no C6 C7 C8 C9 -179.69(14) no C4 C3 C8 C7 2.0(2) no C2 C3 C8 C7 -177.07(13) no C4 C3 C8 C9 179.58(14) no C2 C3 C8 C9 0.5(2) yes C7 C8 C9 C10 -145.78(15) no C3 C8 C9 C10 36.76(19) yes C8 C9 C10 C11 -52.98(18) yes N1 C2 C11 C12 1.8(2) no C3 C2 C11 C12 -177.68(13) no N1 C2 C11 C10 -178.31(13) no C3 C2 C11 C10 2.2(2) yes C9 C10 C11 C2 35.1(2) yes C9 C10 C11 C12 -144.99(15) no C1 N2 C12 C11 6.1(2) no C1 N2 C12 C13 -171.58(12) no C2 C11 C12 N2 -7.2(2) no C10 C11 C12 N2 172.89(14) no C2 C11 C12 C13 170.33(13) no C10 C11 C12 C13 -9.6(2) no N2 C12 C13 C14 -48.08(19) no C11 C12 C13 C14 134.24(15) no N2 C12 C13 C18 128.54(15) no C11 C12 C13 C18 -49.1(2) no C18 C13 C14 C15 0.2(2) no C12 C13 C14 C15 176.87(13) no C13 C14 C15 C16 -1.2(2) no C14 C15 C16 C17 1.0(3) no C15 C16 C17 C18 0.0(3) no C16 C17 C18 C13 -1.0(3) no C14 C13 C18 C17 0.9(2) no C12 C13 C18 C17 -175.85(14) no