#------------------------------------------------------------------------------
#$Date: 2023-06-29 15:21:46 +0200 (Thu 29 de Jun de 2023) $
#$Revision: 284653 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/94/7159405.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_7159405
loop_
_publ_author_name
'Hsueh, Jen-Chun'
'Szu, Fu-En'
'Yu, Yin-Yin'
'Leung, Man-Kit'
_publ_section_title
;
 ortho-Lithiation driven one-pot synthesis of quinazolines
 via [2 + 2 + 2] cascade annulation of halofluorobenzenes with
 nitriles.
;
_journal_issue                   25
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5297
_journal_page_last               5304
_journal_paper_doi               10.1039/d3ob00741c
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C20 H12 Br F N2'
_chemical_formula_weight         379.23
_chemical_name_systematic        6-Bromo-5-fluoro-2,4-diphenylquinazoline
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-03-22 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.5625(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4004(10)
_cell_length_b                   4.9641(3)
_cell_length_c                   19.8649(12)
_cell_measurement_reflns_used    9173
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.08
_cell_measurement_theta_min      2.83
_cell_volume                     1541.88(16)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE, PhotonIII_C28'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            28264
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         78.665
_diffrn_reflns_theta_min         2.826
_diffrn_source                   'I-mu-S microfocus sealed tube'
_exptl_absorpt_coefficient_mu    3.749
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.980
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     390
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+7.7823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1013
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3128
_reflns_number_total             3206
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00741c2.cif
_cod_data_source_block           ic21665
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159405
_shelx_shelxl_version_number     2018/3
_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_min   0.316
_shelx_estimated_absorpt_t_max   0.835
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
Br1 Br 0.79803(2) 1.31735(7) 0.85685(2) 0.01965(12) Uani 1 1 d . . . . .
F1 F 0.67115(13) 0.9899(5) 0.74777(11) 0.0295(5) Uani 1 1 d . . . . .
N1 N 0.86836(17) 0.4614(6) 0.66608(14) 0.0139(5) Uani 1 1 d . . . . .
N2 N 0.71906(17) 0.3791(6) 0.61289(14) 0.0161(6) Uani 1 1 d . . . . .
C1 C 0.7507(2) 0.9225(7) 0.74843(18) 0.0179(7) Uani 1 1 d . . . . .
C2 C 0.8174(2) 1.0505(7) 0.79521(17) 0.0164(7) Uani 1 1 d . . . . .
C3 C 0.9022(2) 0.9865(7) 0.79877(18) 0.0172(7) Uani 1 1 d . . . . .
H3 H 0.948609 1.078305 0.831011 0.021 Uiso 1 1 calc R U . . .
C4 C 0.9174(2) 0.7915(7) 0.75560(17) 0.0157(7) Uani 1 1 d . . . . .
H4 H 0.974541 0.747319 0.758058 0.019 Uiso 1 1 calc R U . . .
C5 C 0.8487(2) 0.6546(7) 0.70721(17) 0.0141(6) Uani 1 1 d . . . . .
C6 C 0.7624(2) 0.7186(7) 0.70241(17) 0.0154(7) Uani 1 1 d . . . . .
C7 C 0.6977(2) 0.5681(7) 0.65145(17) 0.0151(6) Uani 1 1 d . . . . .
C8 C 0.8040(2) 0.3328(7) 0.62129(17) 0.0136(6) Uani 1 1 d . . . . .
C9 C 0.8242(2) 0.1205(7) 0.57651(16) 0.0136(6) Uani 1 1 d . . . . .
C10 C 0.7600(2) -0.0296(7) 0.52923(17) 0.0168(7) Uani 1 1 d . . . . .
H10 H 0.701750 0.007007 0.524834 0.020 Uiso 1 1 calc R U . . .
C11 C 0.7801(2) -0.2315(7) 0.48854(18) 0.0196(7) Uani 1 1 d . . . . .
H11 H 0.735874 -0.333171 0.456795 0.024 Uiso 1 1 calc R U . . .
C12 C 0.8651(2) -0.2842(7) 0.49444(18) 0.0198(7) Uani 1 1 d . . . . .
H12 H 0.878957 -0.421270 0.466373 0.024 Uiso 1 1 calc R U . . .
C13 C 0.9296(2) -0.1380(7) 0.54098(17) 0.0168(7) Uani 1 1 d . . . . .
H13 H 0.987671 -0.176885 0.545247 0.020 Uiso 1 1 calc R U . . .
C14 C 0.9099(2) 0.0659(7) 0.58163(17) 0.0149(6) Uani 1 1 d . . . . .
H14 H 0.954490 0.168226 0.612834 0.018 Uiso 1 1 calc R U . . .
C15 C 0.6065(2) 0.6038(12) 0.6418(2) 0.0175(14) Uani 0.499(4) 1 d G U P A 1
C16 C 0.5705(3) 0.5904(11) 0.69675(19) 0.0223(12) Uani 0.499(4) 1 d G U P A 1
H16A H 0.605891 0.560165 0.743697 0.027 Uiso 0.499(4) 1 calc R U P A 1
C17 C 0.4828(3) 0.6214(12) 0.6830(2) 0.0261(13) Uani 0.499(4) 1 d G U P A 1
H17A H 0.458165 0.612306 0.720513 0.031 Uiso 0.499(4) 1 calc R U P A 1
C18 C 0.4310(2) 0.6657(13) 0.6143(3) 0.0249(14) Uani 0.499(4) 1 d G U P A 1
H18A H 0.371037 0.686900 0.604865 0.030 Uiso 0.499(4) 1 calc R U P A 1
C19 C 0.4670(3) 0.6791(12) 0.5594(2) 0.0256(13) Uani 0.499(4) 1 d G U P A 1
H19A H 0.431636 0.709354 0.512402 0.031 Uiso 0.499(4) 1 calc R U P A 1
C20 C 0.5548(3) 0.6481(11) 0.5731(2) 0.0208(12) Uani 0.499(4) 1 d G U P A 1
H20A H 0.579362 0.657214 0.535585 0.025 Uiso 0.499(4) 1 calc R U P A 1
C15' C 0.6012(2) 0.6139(10) 0.6312(3) 0.0180(14) Uani 0.501(4) 1 d G U P A 2
C16' C 0.5679(3) 0.8693(8) 0.6112(3) 0.0206(12) Uani 0.501(4) 1 d G U P A 2
H16B H 0.604881 1.013301 0.608408 0.025 Uiso 0.501(4) 1 calc R U P A 2
C17' C 0.4805(3) 0.9140(8) 0.5953(3) 0.0218(12) Uani 0.501(4) 1 d G U P A 2
H17B H 0.457686 1.088513 0.581689 0.026 Uiso 0.501(4) 1 calc R U P A 2
C18' C 0.4263(2) 0.7033(10) 0.5994(3) 0.0230(14) Uani 0.501(4) 1 d G U P A 2
H18B H 0.366566 0.733801 0.588563 0.028 Uiso 0.501(4) 1 calc R U P A 2
C19' C 0.4596(3) 0.4479(8) 0.6194(3) 0.0242(13) Uani 0.501(4) 1 d G U P A 2
H19B H 0.422641 0.303872 0.622156 0.029 Uiso 0.501(4) 1 calc R U P A 2
C20' C 0.5471(3) 0.4032(8) 0.6352(3) 0.0222(12) Uani 0.501(4) 1 d G U P A 2
H20B H 0.569836 0.228654 0.648876 0.027 Uiso 0.501(4) 1 calc R U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
_geom_angle_publ_flag
C8 N1 C5 117.3(3) . . ?
C7 N2 C8 119.0(3) . . ?
F1 C1 C2 118.0(3) . . ?
F1 C1 C6 119.5(3) . . ?
C2 C1 C6 122.5(3) . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 Br1 120.7(3) . . ?
C3 C2 Br1 118.8(3) . . ?
C4 C3 C2 119.5(3) . . ?
C3 C4 C5 120.6(3) . . ?
N1 C5 C4 117.5(3) . . ?
N1 C5 C6 121.9(3) . . ?
C4 C5 C6 120.6(3) . . ?
C1 C6 C5 116.2(3) . . ?
C1 C6 C7 127.7(3) . . ?
C5 C6 C7 116.0(3) . . ?
N2 C7 C6 120.6(3) . . ?
N2 C7 C15 116.7(3) . . ?
C6 C7 C15 122.6(3) . . ?
N2 C7 C15' 112.8(3) . . ?
C6 C7 C15' 126.5(3) . . ?
N1 C8 N2 125.2(3) . . ?
N1 C8 C9 118.1(3) . . ?
N2 C8 C9 116.7(3) . . ?
C10 C9 C14 118.8(3) . . ?
C10 C9 C8 121.6(3) . . ?
C14 C9 C8 119.6(3) . . ?
C11 C10 C9 120.9(3) . . ?
C12 C11 C10 119.7(3) . . ?
C13 C12 C11 120.3(3) . . ?
C12 C13 C14 120.3(3) . . ?
C13 C14 C9 120.0(3) . . ?
C16 C15 C20 120.0 . . ?
C16 C15 C7 123.5(3) . . ?
C20 C15 C7 116.5(3) . . ?
C17 C16 C15 120.0 . . ?
C16 C17 C18 120.0 . . ?
C17 C18 C19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C19 C20 C15 120.0 . . ?
C16' C15' C20' 120.0 . . ?
C16' C15' C7 119.9(3) . . ?
C20' C15' C7 120.1(3) . . ?
C17' C16' C15' 120.0 . . ?
C16' C17' C18' 120.0 . . ?
C19' C18' C17' 120.0 . . ?
C18' C19' C20' 120.0 . . ?
C19' C20' C15' 120.0 . . ?
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
Br1 C2 1.895(3) . ?
F1 C1 1.343(4) . ?
N1 C8 1.321(4) . ?
N1 C5 1.361(4) . ?
N2 C7 1.323(4) . ?
N2 C8 1.372(4) . ?
C1 C2 1.361(5) . ?
C1 C6 1.415(5) . ?
C2 C3 1.407(5) . ?
C3 C4 1.365(5) . ?
C4 C5 1.415(5) . ?
C5 C6 1.424(4) . ?
C6 C7 1.436(5) . ?
C7 C15 1.460(4) . ?
C7 C15' 1.528(4) . ?
C8 C9 1.480(5) . ?
C9 C10 1.396(5) . ?
C9 C14 1.405(4) . ?
C10 C11 1.388(5) . ?
C11 C12 1.388(5) . ?
C12 C13 1.382(5) . ?
C13 C14 1.392(5) . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C16 C17 1.3900 . ?
C17 C18 1.3900 . ?
C18 C19 1.3900 . ?
C19 C20 1.3900 . ?
C15' C16' 1.3900 . ?
C15' C20' 1.3900 . ?
C16' C17' 1.3900 . ?
C17' C18' 1.3900 . ?
C18' C19' 1.3900 . ?
C19' C20' 1.3900 . ?
