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#$Date: 2022-07-11 10:58:01 +0300 (Mon, 11 Jul 2022) $
#$Revision: 276748 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/56/8105672.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8105672
loop_
_publ_author_name
'Li, Yong'
'Wu, Yun-Deng'
'Wang, Jingjing'
_publ_section_title
;
 The crystal structure of
 4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-ol, C15H11ClFN3O2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              437
_journal_page_last               438
_journal_paper_doi               10.1515/ncrs-2018-0445
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C15 H11 Cl F N3 O2'
_chemical_formula_sum            'C15 H11 Cl F N3 O2'
_chemical_formula_weight         319.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 115.861(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9430(8)
_cell_length_b                   9.3196(5)
_cell_length_c                   12.5959(8)
_cell_measurement_reflns_used    2077
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.2168
_cell_measurement_theta_min      1.7930
_cell_volume                     1367.21(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -10.00   81.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       11.6246   38.0000  150.0000 91

#__ type_ start__ end____ width___ exp.time_
  2 omega  -62.00   20.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       11.6246  -77.0000   30.0000 82
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0412612000
_diffrn_orient_matrix_UB_12      -0.0067809000
_diffrn_orient_matrix_UB_13      0.0226430000
_diffrn_orient_matrix_UB_21      -0.0424640000
_diffrn_orient_matrix_UB_22      -0.0181179000
_diffrn_orient_matrix_UB_23      -0.0570808000
_diffrn_orient_matrix_UB_31      0.0142882000
_diffrn_orient_matrix_UB_32      -0.0736001000
_diffrn_orient_matrix_UB_33      0.0119778000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5456
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.799
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0572P)²+0.7820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1359
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1838
_reflns_number_total             2497
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0445_suppl.cif
_cod_data_source_block           c4
_cod_original_cell_volume        1367.21(16)
_cod_database_code               8105672
_chemical_oxdiff_formula         'c h n o s cl'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.934
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C1(H1B), C4(H4), C8(H8), C11(H11), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
loop_
_space_group_symop_operation_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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.14134(8) 0.71513(12) 0.27001(8) 0.0732(3) Uani 1 1 d . . . . .
F1 F -0.10006(19) 0.8728(2) 0.4855(2) 0.0848(7) Uani 1 1 d . . . . .
O1 O 0.53829(16) 0.0694(2) 0.72281(15) 0.0408(5) Uani 1 1 d . . . . .
H1 H 0.496095 0.075128 0.755842 0.061 Uiso 1 1 calc GR . . . .
O2 O 0.65394(15) 0.0681(2) 0.59872(15) 0.0393(5) Uani 1 1 d . . . . .
N1 N 0.24197(18) 0.4831(2) 0.54733(18) 0.0363(5) Uani 1 1 d . . . . .
H1A H 0.266363 0.434263 0.611614 0.044 Uiso 1 1 calc R . . . .
N2 N 0.25849(18) 0.5312(2) 0.37509(18) 0.0341(5) Uani 1 1 d . . . . .
N3 N 0.40419(18) 0.4236(2) 0.33419(17) 0.0326(5) Uani 1 1 d . . . . .
C1 C 0.4136(2) 0.2574(3) 0.6049(2) 0.0320(6) Uani 1 1 d . . . . .
H1B H 0.374911 0.260870 0.652099 0.038 Uiso 1 1 calc R . . . .
C2 C 0.5028(2) 0.1633(3) 0.6317(2) 0.0300(6) Uani 1 1 d . . . . .
C3 C 0.5634(2) 0.1599(3) 0.5606(2) 0.0297(6) Uani 1 1 d . . . . .
C4 C 0.5297(2) 0.2450(3) 0.4629(2) 0.0317(6) Uani 1 1 d . . . . .
H4 H 0.568296 0.240384 0.415601 0.038 Uiso 1 1 calc R . . . .
C5 C 0.4365(2) 0.3396(3) 0.4339(2) 0.0278(6) Uani 1 1 d . . . . .
C6 C 0.3798(2) 0.3492(3) 0.5061(2) 0.0276(6) Uani 1 1 d . . . . .
C7 C 0.2917(2) 0.4551(3) 0.4738(2) 0.0296(6) Uani 1 1 d . . . . .
C8 C 0.3174(2) 0.5091(3) 0.3114(2) 0.0355(6) Uani 1 1 d . . . . .
H8 H 0.292991 0.561553 0.241828 0.043 Uiso 1 1 calc R . . . .
C9 C 0.7270(2) 0.0731(3) 0.5407(3) 0.0473(8) Uani 1 1 d . . . . .
H9A H 0.684979 0.042643 0.460252 0.071 Uiso 1 1 calc GR . . . .
H9B H 0.791479 0.010546 0.580295 0.071 Uiso 1 1 calc GR . . . .
H9C H 0.753846 0.169515 0.542337 0.071 Uiso 1 1 calc GR . . . .
C10 C 0.1544(2) 0.5843(3) 0.5284(2) 0.0319(6) Uani 1 1 d . . . . .
C11 C 0.0613(2) 0.5999(3) 0.4194(2) 0.0358(6) Uani 1 1 d . . . . .
H11 H 0.056040 0.544725 0.355754 0.043 Uiso 1 1 calc R . . . .
C12 C -0.0235(2) 0.6971(3) 0.4056(3) 0.0438(7) Uani 1 1 d . . . . .
C13 C -0.0164(3) 0.7770(3) 0.5003(3) 0.0510(8) Uani 1 1 d . . . . .
C14 C 0.0740(3) 0.7611(3) 0.6092(3) 0.0545(8) Uani 1 1 d . . . . .
H14 H 0.077737 0.815198 0.672837 0.065 Uiso 1 1 calc R . . . .
C15 C 0.1599(2) 0.6636(3) 0.6236(2) 0.0434(7) Uani 1 1 d . . . . .
H15 H 0.221345 0.651379 0.697383 0.052 Uiso 1 1 calc R . . . .
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'
Cl Cl 0.1484 0.1585 '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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
C2 O1 H1 109.5 . .
C3 O2 C9 117.5(2) . .
C7 N1 H1A 116.7 . .
C7 N1 C10 126.5(2) . .
C10 N1 H1A 116.7 . .
C7 N2 C8 116.1(2) . .
C8 N3 C5 115.9(2) . .
C2 C1 H1B 119.7 . .
C2 C1 C6 120.6(2) . .
C6 C1 H1B 119.7 . .
O1 C2 C1 124.1(2) . .
O1 C2 C3 116.2(2) . .
C1 C2 C3 119.7(2) . .
O2 C3 C2 114.8(2) . .
O2 C3 C4 124.8(2) . .
C4 C3 C2 120.4(2) . .
C3 C4 H4 120.1 . .
C3 C4 C5 119.9(2) . .
C5 C4 H4 120.1 . .
N3 C5 C4 118.5(2) . .
N3 C5 C6 121.3(2) . .
C6 C5 C4 120.3(2) . .
C1 C6 C7 124.9(2) . .
C5 C6 C1 119.1(2) . .
C5 C6 C7 116.0(2) . .
N1 C7 C6 119.6(2) . .
N2 C7 N1 118.5(2) . .
N2 C7 C6 121.9(2) . .
N2 C8 H8 115.8 . .
N3 C8 N2 128.5(2) . .
N3 C8 H8 115.8 . .
O2 C9 H9A 109.5 . .
O2 C9 H9B 109.5 . .
O2 C9 H9C 109.5 . .
H9A C9 H9B 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C11 C10 N1 121.7(2) . .
C15 C10 N1 118.5(2) . .
C15 C10 C11 119.8(2) . .
C10 C11 H11 120.1 . .
C12 C11 C10 119.8(3) . .
C12 C11 H11 120.1 . .
C11 C12 Cl1 120.0(2) . .
C11 C12 C13 120.0(3) . .
C13 C12 Cl1 120.0(2) . .
F1 C13 C12 119.4(3) . .
F1 C13 C14 119.5(3) . .
C14 C13 C12 121.0(3) . .
C13 C14 H14 120.4 . .
C13 C14 C15 119.2(3) . .
C15 C14 H14 120.4 . .
C10 C15 C14 120.2(3) . .
C10 C15 H15 119.9 . .
C14 C15 H15 119.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C12 1.732(3) .
F1 C13 1.352(3) .
O1 H1 0.8200 .
O1 C2 1.353(3) .
O2 C3 1.358(3) .
O2 C9 1.427(3) .
N1 H1A 0.8600 .
N1 C7 1.365(3) .
N1 C10 1.412(3) .
N2 C7 1.329(3) .
N2 C8 1.342(3) .
N3 C5 1.380(3) .
N3 C8 1.303(3) .
C1 H1B 0.9300 .
C1 C2 1.369(4) .
C1 C6 1.413(3) .
C2 C3 1.426(3) .
C3 C4 1.366(3) .
C4 H4 0.9300 .
C4 C5 1.408(4) .
C5 C6 1.398(3) .
C6 C7 1.427(3) .
C8 H8 0.9300 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 C11 1.384(4) .
C10 C15 1.383(4) .
C11 H11 0.9300 .
C11 C12 1.374(4) .
C12 C13 1.375(4) .
C13 C14 1.368(5) .
C14 H14 0.9300 .
C14 C15 1.385(4) .
C15 H15 0.9300 .
