#------------------------------------------------------------------------------ #$Date: 2016-02-20 16:35:30 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176787 $ #$URL: svn://www.crystallography.net/cod/cif/2/21/44/2214449.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_2214449 loop_ _publ_author_name 'Sheng-Chun Chen' 'Fang-Hua Yin' 'Qun Chen' 'Qi Liu' 'Ming-Yang He' _publ_section_title ; 6-Amino-2-(fluoromethyl)-3-(2-methylphenyl)quinazolin-4(3H)-one ; _journal_coeditor_code XU2266 _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3109 _journal_page_last o3109 _journal_paper_doi 10.1107/S1600536807026670 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C16 H14 F N3 O' _chemical_formula_moiety 'C16 H14 F N3 O' _chemical_formula_sum 'C16 H14 F N3 O' _chemical_formula_weight 283.30 _chemical_melting_point 470 _chemical_name_systematic ; 6-Amino-2-(fluoromethyl)-3-(2-methylphenyl)quinazolin-4(3H)-one ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.24(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.3100(13) _cell_length_b 12.310(3) _cell_length_c 17.658(4) _cell_measurement_reflns_used 732 _cell_measurement_temperature 291(2) _cell_measurement_theta_max 25.5 _cell_measurement_theta_min 2.1 _cell_volume 1371.6(5) _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Bruker, 2000)' _diffrn_ambient_temperature 291(2) _diffrn_measured_fraction_theta_full 1.00 _diffrn_measured_fraction_theta_max 1.00 _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.019 _diffrn_reflns_av_sigmaI/netI 0.028 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 5223 _diffrn_reflns_theta_full 26.0 _diffrn_reflns_theta_max 26.0 _diffrn_reflns_theta_min 2.0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 592 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _refine_diff_density_max 0.39 _refine_diff_density_min -0.36 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 200 _refine_ls_number_reflns 2691 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all 0.076 _refine_ls_R_factor_gt 0.063 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0562P)^2^+1.1526P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.149 _refine_ls_wR_factor_ref 0.154 _reflns_number_gt 2172 _reflns_number_total 2691 _reflns_threshold_expression I>2\s(I) _cod_data_source_file xu2266.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2214449 _cod_database_fobs_code 2214449 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_type_symbol _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 C C1 0.3272(4) 0.37992(19) 0.06660(14) 0.0351(5) Uani d . 1 B . C C2 0.2262(3) 0.29811(18) 0.01924(13) 0.0311(5) Uani d . 1 . . C C3 0.0418(4) 0.3265(2) -0.02108(14) 0.0378(6) Uani d . 1 . . H H3 -0.0084 0.3975 -0.0197 0.045 Uiso calc R 1 . . C C4 -0.0646(4) 0.2485(2) -0.06276(14) 0.0395(6) Uani d . 1 . . C C5 0.0130(4) 0.1430(2) -0.06377(14) 0.0435(6) Uani d . 1 . . H H5 -0.0587 0.0902 -0.0914 0.052 Uiso calc R 1 . . C C6 0.1975(4) 0.1146(2) -0.02386(14) 0.0403(6) Uani d . 1 . . H H6 0.2497 0.0440 -0.0259 0.048 Uiso calc R 1 . . C C7 0.3005(4) 0.19287(19) 0.01852(13) 0.0333(5) Uani d . 1 B . C C8 0.5704(4) 0.23229(19) 0.10110(13) 0.0334(5) Uani d . 1 B . C C9 0.7671(5) 0.2024(2) 0.14313(18) 0.0559(8) Uani d . 1 . . H H9A 0.7379 0.1994 0.1964 0.067 Uiso d PR 0.50 A 1 H H9C 0.8160 0.1327 0.1262 0.067 Uiso d PR 0.50 A 1 H H9B 0.8744 0.2560 0.1338 0.067 Uiso d R 1 . . F F1 0.8229(5) 0.1004(3) 0.1308(2) 0.0569(9) Uani d P 0.50 B 2 F F2 0.7462(5) 0.1867(3) 0.21687(18) 0.0554(8) Uani d P 0.50 B 2 C C10 0.5861(3) 0.40942(19) 0.16752(14) 0.0346(6) Uani d . 1 B . C C11 0.7616(4) 0.4745(2) 0.15056(15) 0.0425(6) Uani d . 1 . . H H11 0.8214 0.4735 0.1025 0.051 Uiso calc R 1 . . C C12 0.8429(4) 0.5396(2) 0.20645(19) 0.0557(8) Uani d . 1 . . H H12 0.9575 0.5847 0.1962 0.067 Uiso calc R 1 . . C C13 0.7555(5) 0.5383(2) 0.27761(17) 0.0523(8) Uani d . 1 . . H H13 0.8140 0.5810 0.3158 0.063 Uiso calc R 1 . . C C14 0.5837(4) 0.4750(2) 0.29274(15) 0.0425(6) Uani d . 1 . . H H14 0.5252 0.4767 0.3410 0.051 Uiso calc R 1 . . C C15 0.4929(4) 0.4076(2) 0.23813(14) 0.0364(5) Uani d . 1 . . C C16 0.3045(5) 0.3415(3) 0.25512(18) 0.0569(8) Uani d . 1 . . H H16A 0.1814 0.3747 0.2329 0.085 Uiso calc R 1 . . H H16B 0.2867 0.3367 0.3090 0.085 Uiso calc R 1 . . H H16C 0.3225 0.2699 0.2346 0.085 Uiso calc R 1 . . N N1 0.5001(3) 0.33912(16) 0.10830(11) 0.0328(5) Uani d . 1 . . N N2 0.4853(3) 0.16129(16) 0.05817(12) 0.0379(5) Uani d . 1 . . N N3 -0.2479(4) 0.2761(2) -0.10214(15) 0.0563(7) Uani d . 1 . . H H3C -0.2256 0.2587 -0.1510 0.068 Uiso d R 1 . . H H3A -0.2934 0.3419 -0.1011 0.068 Uiso d R 1 . . O O1 0.2752(3) 0.47363(14) 0.07204(12) 0.0544(6) Uani d . 1 . . 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 C1 0.0318(12) 0.0284(12) 0.0451(14) 0.0018(9) -0.0125(10) -0.0001(10) C2 0.0304(11) 0.0321(12) 0.0309(11) 0.0006(9) -0.0084(9) 0.0007(9) C3 0.0352(12) 0.0393(13) 0.0389(13) 0.0000(10) -0.0164(10) 0.0014(10) C4 0.0374(13) 0.0440(14) 0.0369(13) -0.0099(11) -0.0137(10) 0.0058(11) C5 0.0550(16) 0.0387(14) 0.0365(13) -0.0176(12) -0.0145(11) -0.0029(11) C6 0.0457(14) 0.0305(12) 0.0447(14) -0.0049(11) -0.0105(11) -0.0040(10) C7 0.0303(11) 0.0342(12) 0.0352(12) -0.0017(9) -0.0002(9) 0.0016(10) C8 0.0276(11) 0.0389(13) 0.0338(12) 0.0036(9) -0.0015(9) -0.0023(10) C9 0.0507(17) 0.0490(16) 0.068(2) 0.0209(13) -0.0260(15) -0.0128(14) F1 0.0510(18) 0.0493(19) 0.070(2) -0.0051(15) -0.0137(16) -0.0006(16) F2 0.0490(18) 0.069(2) 0.0482(19) -0.0034(16) -0.0059(15) -0.0051(16) C10 0.0257(11) 0.0329(12) 0.0450(14) 0.0122(9) -0.0143(10) -0.0088(10) C11 0.0417(14) 0.0442(14) 0.0416(14) -0.0082(11) -0.0028(11) -0.0052(11) C12 0.0375(14) 0.0478(16) 0.082(2) -0.0119(12) -0.0077(14) -0.0150(15) C13 0.0586(17) 0.0409(15) 0.0571(18) -0.0022(13) -0.0304(15) -0.0072(13) C14 0.0517(15) 0.0404(14) 0.0353(13) 0.0042(12) -0.0125(11) -0.0020(11) C15 0.0309(11) 0.0343(12) 0.0440(14) 0.0076(9) -0.0041(10) -0.0053(10) C16 0.0514(17) 0.0582(18) 0.0611(19) -0.0227(14) 0.0034(14) -0.0093(15) N1 0.0300(10) 0.0308(10) 0.0375(11) 0.0019(8) -0.0132(8) -0.0031(8) N2 0.0386(11) 0.0300(10) 0.0450(12) 0.0034(8) -0.0108(9) -0.0038(9) N3 0.0448(13) 0.0524(15) 0.0716(17) -0.0076(11) -0.0076(12) -0.0127(12) O1 0.0524(11) 0.0316(9) 0.0790(14) 0.0153(8) -0.0330(10) -0.0144(9) 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' F F 0.0171 0.0103 '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 O1 C1 N1 120.8(2) O1 C1 C2 126.2(2) N1 C1 C2 113.00(19) C7 C2 C3 120.7(2) C7 C2 C1 120.6(2) C3 C2 C1 118.6(2) C4 C3 C2 119.8(2) C4 C3 H3 120.1 C2 C3 H3 120.1 C3 C4 N3 119.9(2) C3 C4 C5 119.1(2) N3 C4 C5 121.0(2) C4 C5 C6 121.3(2) C4 C5 H5 119.4 C6 C5 H5 119.4 C7 C6 C5 119.1(2) C7 C6 H6 120.5 C5 C6 H6 120.5 C2 C7 C6 120.1(2) C2 C7 N2 122.3(2) C6 C7 N2 117.5(2) N2 C8 N1 124.6(2) N2 C8 C9 118.4(2) N1 C8 C9 116.9(2) F1 C9 F2 92.9(3) F1 C9 C8 112.0(3) F2 C9 C8 116.1(3) F1 C9 H9A 100.1 C8 C9 H9A 109.5 F2 C9 H9C 102.1 C8 C9 H9C 109.5 H9A C9 H9C 109.5 F1 C9 H9B 115.9 F2 C9 H9B 110.0 C8 C9 H9B 109.4 H9A C9 H9B 109.5 H9C C9 H9B 109.5 C15 C10 C11 122.9(2) C15 C10 N1 118.6(2) C11 C10 N1 118.5(2) C12 C11 C10 118.4(3) C12 C11 H11 120.8 C10 C11 H11 120.8 C13 C12 C11 120.1(3) C13 C12 H12 120.0 C11 C12 H12 120.0 C14 C13 C12 120.6(3) C14 C13 H13 119.7 C12 C13 H13 119.7 C13 C14 C15 122.0(3) C13 C14 H14 119.0 C15 C14 H14 119.0 C10 C15 C14 116.1(2) C10 C15 C16 122.7(2) C14 C15 C16 121.2(2) C15 C16 H16A 109.5 C15 C16 H16B 109.5 H16A C16 H16B 109.5 C15 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 C8 N1 C1 122.38(19) C8 N1 C10 120.48(18) C1 N1 C10 116.64(18) C8 N2 C7 116.8(2) C4 N3 H3C 106.8 C4 N3 H3A 119.8 H3C N3 H3A 107.3 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 O1 1.203(3) C1 N1 1.407(3) C1 C2 1.454(3) C2 C7 1.378(3) C2 C3 1.406(3) C3 C4 1.382(3) C3 H3 0.9300 C4 N3 1.389(3) C4 C5 1.388(4) C5 C6 1.403(4) C5 H5 0.9300 C6 C7 1.381(3) C6 H6 0.9300 C7 N2 1.412(3) C8 N2 1.274(3) C8 N1 1.394(3) C8 C9 1.490(3) C9 F1 1.322(4) C9 F2 1.324(5) C9 H9A 0.9601 C9 H9C 0.9599 C9 H9B 0.9600 F1 H9C 0.4086 F2 H9A 0.3969 C10 C15 1.381(4) C10 C11 1.400(4) C10 N1 1.460(3) C11 C12 1.369(4) C11 H11 0.9300 C12 C13 1.375(4) C12 H12 0.9300 C13 C14 1.363(4) C13 H13 0.9300 C14 C15 1.393(3) C14 H14 0.9300 C15 C16 1.473(4) C16 H16A 0.9600 C16 H16B 0.9600 C16 H16C 0.9600 N3 H3C 0.8999 N3 H3A 0.8599 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 _geom_hbond_publ_flag N3 H3A O1 3_565 0.86 2.33 3.132(3) 155 yes N3 H3C F2 4_465 0.90 2.43 3.229(4) 147 yes C3 H3 O1 3_565 0.93 2.49 3.294(3) 145 yes