#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/45/2204552.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_2204552 loop_ _publ_author_name 'Daqing Shi' 'Zhengyi Li' 'Chunling Shi' 'Qiya Zhuang' 'Yong Zhang' _publ_section_title ; 3-(4-Bromophenyl)-2,2-dimethyl-2,3-dihydroquinazolin-4(1H)-one ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1992 _journal_page_last o1994 _journal_paper_doi 10.1107/S1600536804025115 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C16 H15 Br N2 O' _chemical_formula_moiety 'C16 H15 Br N2 O' _chemical_formula_sum 'C16 H15 Br N2 O' _chemical_formula_weight 331.21 _chemical_melting_point 537.5(5) _chemical_name_systematic ; 3-(4-Bromophenyl)-2,2-dimethyl-2,3-dihydroquinazolin-4(1H)-one ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 65.397(4) _cell_angle_beta 88.452(6) _cell_angle_gamma 86.194(6) _cell_formula_units_Z 2 _cell_length_a 6.8865(6) _cell_length_b 9.9508(6) _cell_length_c 11.6702(8) _cell_measurement_reflns_used 2946 _cell_measurement_temperature 193(2) _cell_measurement_theta_max 25.3 _cell_measurement_theta_min 3.5 _cell_volume 725.51(9) _computing_cell_refinement CrystalClear _computing_data_collection 'CrystalClear (Rigaku, 2000)' _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2003)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 193(2) _diffrn_detector_area_resol_mean 7.31 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71070 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 7155 _diffrn_reflns_theta_full 25.35 _diffrn_reflns_theta_max 25.35 _diffrn_reflns_theta_min 3.52 _exptl_absorpt_coefficient_mu 2.830 _exptl_absorpt_correction_T_max 0.6602 _exptl_absorpt_correction_T_min 0.3319 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Jacobson, 1998)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.516 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 336 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.360 _refine_diff_density_min -0.500 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 188 _refine_ls_number_reflns 2623 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0312 _refine_ls_R_factor_gt 0.0274 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0402P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.0685 _reflns_number_gt 2325 _reflns_number_total 2623 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ob6417.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '537-538' was changed to '537.5(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 '537-538' was changed to '537.5(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_original_sg_symbol_Hall '-p 1' _cod_database_code 2204552 _cod_database_fobs_code 2204552 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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_type_symbol Br1 -0.32962(3) -0.18161(2) 1.02521(2) 0.03688(11) Uani d . 1 Br O1 -0.16653(19) 0.28373(17) 0.45556(14) 0.0312(4) Uani d . 1 O N1 0.1215(2) 0.19553(18) 0.55721(15) 0.0204(4) Uani d . 1 N N2 0.4172(3) 0.2491(2) 0.44279(18) 0.0273(4) Uani d . 1 N C1 0.0132(3) 0.2848(2) 0.45484(19) 0.0205(4) Uani d . 1 C C2 0.3339(3) 0.2146(2) 0.56747(19) 0.0242(5) Uani d . 1 C C3 0.3246(3) 0.3513(2) 0.3383(2) 0.0228(4) Uani d . 1 C C4 0.4222(3) 0.4264(3) 0.2243(2) 0.0316(5) Uani d . 1 C H4 0.5591 0.4102 0.2196 0.038 Uiso calc R 1 H C5 0.3210(3) 0.5230(3) 0.1196(2) 0.0335(5) Uani d . 1 C H5 0.3894 0.5732 0.0433 0.040 Uiso calc R 1 H C6 0.1204(3) 0.5491(2) 0.1227(2) 0.0305(5) Uani d . 1 C H6 0.0520 0.6169 0.0498 0.037 Uiso calc R 1 H C7 0.0230(3) 0.4746(2) 0.2335(2) 0.0254(5) Uani d . 1 C H7 -0.1142 0.4909 0.2367 0.030 Uiso calc R 1 H C8 0.1217(3) 0.3761(2) 0.34075(19) 0.0209(4) Uani d . 1 C C9 0.0184(3) 0.1062(2) 0.66984(19) 0.0211(4) Uani d . 1 C C10 -0.0021(3) -0.0420(2) 0.6987(2) 0.0255(5) Uani d . 1 C H10 0.0534 -0.0844 0.6450 0.031 Uiso calc R 1 H C11 -0.1030(3) -0.1284(2) 0.8054(2) 0.0269(5) Uani d . 1 C H11 -0.1175 -0.2301 0.8254 0.032 Uiso calc R 1 H C12 -0.1826(3) -0.0645(2) 0.88246(19) 0.0242(4) Uani d . 1 C C13 -0.1625(3) 0.0825(2) 0.8558(2) 0.0274(5) Uani d . 1 C H13 -0.2163 0.1242 0.9104 0.033 Uiso calc R 1 H C14 -0.0627(3) 0.1683(2) 0.7480(2) 0.0257(5) Uani d . 1 C H14 -0.0498 0.2702 0.7276 0.031 Uiso calc R 1 H C15 0.4351(3) 0.0722(3) 0.6580(2) 0.0349(5) Uani d . 1 C H15A 0.4094 -0.0080 0.6335 0.052 Uiso calc R 1 H H15B 0.3861 0.0483 0.7435 0.052 Uiso calc R 1 H H15C 0.5756 0.0836 0.6558 0.052 Uiso calc R 1 H C16 0.3563(3) 0.3399(3) 0.6087(2) 0.0318(5) Uani d . 1 C H16A 0.4948 0.3531 0.6146 0.048 Uiso calc R 1 H H16B 0.2947 0.3150 0.6911 0.048 Uiso calc R 1 H H16C 0.2936 0.4319 0.5467 0.048 Uiso calc R 1 H H2 0.525(4) 0.253(3) 0.443(2) 0.030(7) Uiso 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 Br1 0.03586(16) 0.03531(16) 0.02981(16) -0.00680(11) 0.01102(11) -0.00393(11) O1 0.0149(7) 0.0383(9) 0.0335(9) -0.0022(6) 0.0017(6) -0.0081(7) N1 0.0151(8) 0.0226(9) 0.0226(9) -0.0037(7) 0.0024(7) -0.0082(7) N2 0.0118(9) 0.0415(11) 0.0293(11) -0.0020(8) 0.0028(8) -0.0156(9) C1 0.0184(10) 0.0197(10) 0.0253(11) -0.0023(8) 0.0024(9) -0.0113(9) C2 0.0162(10) 0.0308(12) 0.0252(11) -0.0055(9) 0.0012(9) -0.0106(9) C3 0.0199(10) 0.0265(11) 0.0260(11) -0.0050(9) 0.0032(9) -0.0146(9) C4 0.0220(11) 0.0437(14) 0.0316(13) -0.0099(10) 0.0089(10) -0.0176(11) C5 0.0397(13) 0.0358(13) 0.0267(12) -0.0150(11) 0.0123(10) -0.0136(10) C6 0.0409(13) 0.0238(11) 0.0253(12) -0.0026(10) 0.0014(10) -0.0086(9) C7 0.0240(10) 0.0233(11) 0.0300(12) -0.0011(9) 0.0015(9) -0.0125(9) C8 0.0203(10) 0.0211(10) 0.0241(11) -0.0034(8) 0.0025(9) -0.0121(9) C9 0.0183(10) 0.0226(11) 0.0219(11) -0.0033(8) 0.0014(8) -0.0085(9) C10 0.0286(11) 0.0243(11) 0.0268(12) -0.0028(9) 0.0023(9) -0.0138(9) C11 0.0324(11) 0.0188(10) 0.0273(12) -0.0037(9) -0.0011(9) -0.0071(9) C12 0.0201(10) 0.0267(11) 0.0217(11) -0.0026(9) 0.0002(9) -0.0058(9) C13 0.0260(11) 0.0301(12) 0.0298(12) -0.0037(9) 0.0054(9) -0.0161(10) C14 0.0254(11) 0.0216(11) 0.0334(12) -0.0057(9) 0.0044(9) -0.0142(9) C15 0.0224(11) 0.0397(14) 0.0365(14) 0.0011(10) -0.0039(10) -0.0101(11) C16 0.0285(11) 0.0393(13) 0.0312(13) -0.0131(10) 0.0039(10) -0.0170(11) 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' Br Br -0.2901 2.4595 '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' 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 C9 117.44(15) y C1 N1 C2 122.19(15) y C9 N1 C2 118.55(16) y C3 N2 C2 120.15(17) y C3 N2 H2 115.3(19) ? C2 N2 H2 111.2(19) ? O1 C1 N1 121.48(18) y O1 C1 C8 121.87(18) y N1 C1 C8 116.55(16) y N2 C2 N1 106.34(16) y N2 C2 C15 107.53(17) no N1 C2 C15 110.81(16) no N2 C2 C16 111.52(17) no N1 C2 C16 109.40(16) no C15 C2 C16 111.12(19) ? N2 C3 C8 119.28(18) ? N2 C3 C4 122.48(19) ? C8 C3 C4 118.1(2) ? C5 C4 C3 120.4(2) ? C5 C4 H4 119.8 ? C3 C4 H4 119.8 ? C4 C5 C6 121.5(2) ? C4 C5 H5 119.3 ? C6 C5 H5 119.3 ? C7 C6 C5 118.6(2) ? C7 C6 H6 120.7 ? C5 C6 H6 120.7 ? C6 C7 C8 121.11(19) ? C6 C7 H7 119.4 ? C8 C7 H7 119.4 ? C7 C8 C3 120.33(18) ? C7 C8 C1 120.44(17) ? C3 C8 C1 118.95(18) ? C10 C9 C14 119.94(18) ? C10 C9 N1 119.61(17) ? C14 C9 N1 120.44(17) ? C11 C10 C9 120.26(18) ? C11 C10 H10 119.9 ? C9 C10 H10 119.9 ? C10 C11 C12 118.95(19) ? C10 C11 H11 120.5 ? C12 C11 H11 120.5 ? C13 C12 C11 121.61(19) ? C13 C12 Br1 119.58(16) ? C11 C12 Br1 118.78(15) ? C12 C13 C14 118.92(19) ? C12 C13 H13 120.5 ? C14 C13 H13 120.5 ? C13 C14 C9 120.32(19) ? C13 C14 H14 119.8 ? C9 C14 H14 119.8 ? C2 C15 H15A 109.5 ? C2 C15 H15B 109.5 ? H15A C15 H15B 109.5 ? C2 C15 H15C 109.5 ? H15A C15 H15C 109.5 ? H15B C15 H15C 109.5 ? C2 C16 H16A 109.5 ? C2 C16 H16B 109.5 ? H16A C16 H16B 109.5 ? C2 C16 H16C 109.5 ? H16A C16 H16C 109.5 ? H16B C16 H16C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Br1 C12 1.899(2) ? O1 C1 1.238(2) y N1 C1 1.360(3) y N1 C9 1.443(2) y N1 C2 1.502(2) y N2 C3 1.361(3) y N2 C2 1.459(3) y N2 H2 0.75(2) ? C1 C8 1.478(3) ? C2 C15 1.508(3) ? C2 C16 1.529(3) ? C3 C8 1.404(3) ? C3 C4 1.404(3) ? C4 C5 1.372(3) ? C4 H4 0.9500 ? C5 C6 1.391(3) ? C5 H5 0.9500 ? C6 C7 1.376(3) ? C6 H6 0.9500 ? C7 C8 1.388(3) ? C7 H7 0.9500 ? C9 C10 1.386(3) ? C9 C14 1.386(3) ? C10 C11 1.384(3) ? C10 H10 0.9500 ? C11 C12 1.386(3) ? C11 H11 0.9500 ? C12 C13 1.378(3) ? C13 C14 1.386(3) ? C13 H13 0.9500 ? C14 H14 0.9500 ? C15 H15A 0.9800 ? C15 H15B 0.9800 ? C15 H15C 0.9800 ? C16 H16A 0.9800 ? C16 H16B 0.9800 ? C16 H16C 0.9800 ? 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 C16 H16B Br1 2_557 0.98 3.02 3.894(2) 149 N2 H2 O1 1_655 0.75(2) 2.18(3) 2.925(2) 173(2) 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 C9 N1 C1 O1 -3.9(3) y C2 N1 C1 O1 -168.31(18) y C9 N1 C1 C8 179.59(16) y C2 N1 C1 C8 15.2(3) y C3 N2 C2 N1 46.0(2) y C3 N2 C2 C15 164.70(18) ? C3 N2 C2 C16 -73.2(2) ? C1 N1 C2 N2 -40.1(2) y C9 N1 C2 N2 155.65(16) y C1 N1 C2 C15 -156.71(18) ? C9 N1 C2 C15 39.1(2) ? C1 N1 C2 C16 80.4(2) no C9 N1 C2 C16 -83.8(2) no C2 N2 C3 C8 -27.3(3) y C2 N2 C3 C4 157.40(19) y N2 C3 C4 C5 176.6(2) ? C8 C3 C4 C5 1.3(3) ? C3 C4 C5 C6 -0.3(3) ? C4 C5 C6 C7 -0.6(3) ? C5 C6 C7 C8 0.5(3) ? C6 C7 C8 C3 0.5(3) ? C6 C7 C8 C1 -173.26(18) ? N2 C3 C8 C7 -176.89(18) ? C4 C3 C8 C7 -1.4(3) ? N2 C3 C8 C1 -3.0(3) ? C4 C3 C8 C1 172.51(18) ? O1 C1 C8 C7 6.1(3) ? N1 C1 C8 C7 -177.48(17) ? O1 C1 C8 C3 -167.82(19) ? N1 C1 C8 C3 8.6(3) ? C1 N1 C9 C10 100.2(2) ? C2 N1 C9 C10 -94.9(2) ? C1 N1 C9 C14 -78.7(2) ? C2 N1 C9 C14 86.2(2) ? C14 C9 C10 C11 -0.1(3) ? N1 C9 C10 C11 -179.04(19) ? C9 C10 C11 C12 0.0(3) ? C10 C11 C12 C13 -0.4(3) ? C10 C11 C12 Br1 177.58(16) ? C11 C12 C13 C14 1.0(3) ? Br1 C12 C13 C14 -176.97(16) ? C12 C13 C14 C9 -1.2(3) ? C10 C9 C14 C13 0.7(3) ? N1 C9 C14 C13 179.64(19) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 611584 2 PubChem 701683