#------------------------------------------------------------------------------
#$Date: 2023-06-29 16:21:46 +0300 (Thu, 29 Jun 2023) $
#$Revision: 284653 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/94/7159404.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_7159404
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
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-03-13 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                93.6965(6)
_cell_angle_beta                 93.9425(6)
_cell_angle_gamma                101.9771(6)
_cell_formula_units_Z            4
_cell_length_a                   7.3882(2)
_cell_length_b                   9.8687(3)
_cell_length_c                   21.9346(6)
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.60
_cell_measurement_theta_min      4.05
_cell_volume                     1555.69(8)
_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 0.993
_diffrn_measured_fraction_theta_max 0.955
_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  0.0265
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23763
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.111
_diffrn_reflns_theta_min         2.025
_diffrn_source                   'I-mu-S microfocus sealed tube'
_exptl_absorpt_coefficient_mu    3.715
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6943
_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_colour            colourless
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.898
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         6441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0271
_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)+(0.0424P)²+1.5260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0758
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6299
_reflns_number_total             6441
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00741c2.cif
_cod_data_source_block           ic21654
_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_database_code               7159404
_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   0.356
_shelx_estimated_absorpt_t_max   0.708
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.72378(2) 0.60614(2) -0.11327(2) 0.01592(6) Uani 1 1 d . . . . .
F1 F 0.52266(16) 0.13028(11) 0.04312(5) 0.0191(2) Uani 1 1 d . . . . .
N1 N 0.8421(2) 0.59818(15) 0.02092(7) 0.0120(3) Uani 1 1 d . . . . .
N2 N 0.8590(2) 0.51403(15) 0.12048(7) 0.0126(3) Uani 1 1 d . . . . .
C1 C 0.7351(2) 0.47430(17) -0.00137(8) 0.0113(3) Uani 1 1 d . . . . .
C2 C 0.6631(2) 0.45610(19) -0.06382(8) 0.0137(3) Uani 1 1 d . . . . .
C3 C 0.5520(2) 0.33345(19) -0.08816(8) 0.0158(3) Uani 1 1 d . . . . .
H3 H 0.505869 0.323481 -0.130077 0.019 Uiso 1 1 calc R U . . .
C4 C 0.5059(2) 0.22211(19) -0.05134(8) 0.0163(3) Uani 1 1 d . . . . .
H4 H 0.428164 0.136846 -0.068023 0.020 Uiso 1 1 calc R U . . .
C5 C 0.5742(2) 0.23795(18) 0.00877(8) 0.0142(3) Uani 1 1 d . . . . .
C6 C 0.6915(2) 0.36124(18) 0.03626(8) 0.0117(3) Uani 1 1 d . . . . .
C7 C 0.7646(2) 0.38960(17) 0.09932(8) 0.0119(3) Uani 1 1 d . . . . .
C8 C 0.7434(2) 0.28391(18) 0.14538(8) 0.0128(3) Uani 1 1 d . . . . .
C9 C 0.8021(3) 0.15940(19) 0.13550(9) 0.0162(3) Uani 1 1 d . . . . .
H9 H 0.851949 0.138787 0.098064 0.019 Uiso 1 1 calc R U . . .
C10 C 0.7876(3) 0.0652(2) 0.18046(9) 0.0189(4) Uani 1 1 d . . . . .
H10 H 0.829016 -0.019029 0.173834 0.023 Uiso 1 1 calc R U . . .
C11 C 0.7128(3) 0.0942(2) 0.23501(9) 0.0187(4) Uani 1 1 d . . . . .
H11 H 0.699734 0.028545 0.265083 0.022 Uiso 1 1 calc R U . . .
C12 C 0.6571(3) 0.2193(2) 0.24560(8) 0.0177(4) Uani 1 1 d . . . . .
H12 H 0.607800 0.239838 0.283150 0.021 Uiso 1 1 calc R U . . .
C13 C 0.6737(2) 0.31398(19) 0.20124(8) 0.0148(3) Uani 1 1 d . . . . .
H13 H 0.637500 0.400022 0.208821 0.018 Uiso 1 1 calc R U . . .
C14 C 0.8967(2) 0.61361(18) 0.07986(8) 0.0118(3) Uani 1 1 d . . . . .
C15 C 1.0141(2) 0.74935(18) 0.10413(8) 0.0129(3) Uani 1 1 d . . . . .
C16 C 1.1073(3) 0.76642(19) 0.16273(8) 0.0157(3) Uani 1 1 d . . . . .
H16 H 1.091408 0.691278 0.188219 0.019 Uiso 1 1 calc R U . . .
C17 C 1.2230(3) 0.8928(2) 0.18378(9) 0.0192(4) Uani 1 1 d . . . . .
H17 H 1.285354 0.903760 0.223717 0.023 Uiso 1 1 calc R U . . .
C18 C 1.2483(3) 1.00322(19) 0.14684(9) 0.0191(4) Uani 1 1 d . . . . .
H18 H 1.328557 1.089227 0.161213 0.023 Uiso 1 1 calc R U . . .
C19 C 1.1551(3) 0.98701(19) 0.08862(9) 0.0181(4) Uani 1 1 d . . . . .
H19 H 1.171674 1.062442 0.063298 0.022 Uiso 1 1 calc R U . . .
C20 C 1.0384(2) 0.86154(19) 0.06732(8) 0.0152(3) Uani 1 1 d . . . . .
H20 H 0.974675 0.851610 0.027637 0.018 Uiso 1 1 calc R U . . .
Br2 Br 0.22820(3) -0.24686(2) 0.56200(2) 0.01727(6) Uani 1 1 d . . . . .
F2 F 0.38161(16) 0.03243(11) 0.33067(5) 0.0202(2) Uani 1 1 d . . . . .
N3 N 0.2136(2) 0.04905(15) 0.53854(7) 0.0117(3) Uani 1 1 d . . . . .
N4 N 0.2372(2) 0.25638(15) 0.48622(7) 0.0121(3) Uani 1 1 d . . . . .
C21 C 0.2548(2) -0.01807(17) 0.48721(8) 0.0112(3) Uani 1 1 d . . . . .
C22 C 0.2701(2) -0.15933(18) 0.48880(8) 0.0139(3) Uani 1 1 d . . . . .
C23 C 0.3146(2) -0.23074(18) 0.43849(9) 0.0166(3) Uani 1 1 d . . . . .
H23 H 0.321850 -0.325446 0.440076 0.020 Uiso 1 1 calc R U . . .
C24 C 0.3495(3) -0.16451(19) 0.38453(9) 0.0175(4) Uani 1 1 d . . . . .
H24 H 0.381369 -0.213849 0.349650 0.021 Uiso 1 1 calc R U . . .
C25 C 0.3374(2) -0.02929(18) 0.38243(8) 0.0137(3) Uani 1 1 d . . . . .
C26 C 0.2849(2) 0.04881(18) 0.43206(8) 0.0118(3) Uani 1 1 d . . . . .
C27 C 0.2673(2) 0.19082(18) 0.43434(8) 0.0116(3) Uani 1 1 d . . . . .
C28 C 0.2780(2) 0.27546(18) 0.38046(8) 0.0123(3) Uani 1 1 d . . . . .
C29 C 0.1645(2) 0.23043(19) 0.32634(8) 0.0153(3) Uani 1 1 d . . . . .
H29 H 0.080724 0.142612 0.322966 0.018 Uiso 1 1 calc R U . . .
C30 C 0.1737(3) 0.3136(2) 0.27737(8) 0.0176(4) Uani 1 1 d . . . . .
H30 H 0.094661 0.283450 0.240903 0.021 Uiso 1 1 calc R U . . .
C31 C 0.2987(3) 0.44104(19) 0.28184(8) 0.0160(3) Uani 1 1 d . . . . .
H31 H 0.306450 0.497184 0.248132 0.019 Uiso 1 1 calc R U . . .
C32 C 0.4122(2) 0.48642(18) 0.33545(8) 0.0150(3) Uani 1 1 d . . . . .
H32 H 0.498593 0.572993 0.338194 0.018 Uiso 1 1 calc R U . . .
C33 C 0.3997(2) 0.40525(18) 0.38512(8) 0.0136(3) Uani 1 1 d . . . . .
H33 H 0.473976 0.438115 0.422306 0.016 Uiso 1 1 calc R U . . .
C34 C 0.2109(2) 0.18167(18) 0.53623(8) 0.0112(3) Uani 1 1 d . . . . .
C35 C 0.1708(2) 0.25593(17) 0.59288(8) 0.0122(3) Uani 1 1 d . . . . .
C36 C 0.1740(3) 0.19356(19) 0.64829(8) 0.0156(3) Uani 1 1 d . . . . .
H36 H 0.203107 0.104346 0.649446 0.019 Uiso 1 1 calc R U . . .
C37 C 0.1349(3) 0.2616(2) 0.70166(8) 0.0188(4) Uani 1 1 d . . . . .
H37 H 0.138822 0.219419 0.739315 0.023 Uiso 1 1 calc R U . . .
C38 C 0.0900(3) 0.3915(2) 0.69999(8) 0.0180(4) Uani 1 1 d . . . . .
H38 H 0.062839 0.437866 0.736462 0.022 Uiso 1 1 calc R U . . .
C39 C 0.0850(3) 0.45355(19) 0.64491(8) 0.0163(3) Uani 1 1 d . . . . .
H39 H 0.052963 0.541770 0.643750 0.020 Uiso 1 1 calc R U . . .
C40 C 0.1268(2) 0.38683(18) 0.59149(8) 0.0139(3) Uani 1 1 d . . . . .
H40 H 0.125506 0.430257 0.554097 0.017 Uiso 1 1 calc R U . . .
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
C14 N1 C1 117.39(15) . . ?
C7 N2 C14 118.12(15) . . ?
N1 C1 C2 119.26(16) . . ?
N1 C1 C6 121.73(15) . . ?
C2 C1 C6 119.01(15) . . ?
C3 C2 C1 121.37(17) . . ?
C3 C2 Br1 120.09(14) . . ?
C1 C2 Br1 118.54(13) . . ?
C2 C3 C4 120.14(17) . . ?
C5 C4 C3 119.18(17) . . ?
F1 C5 C4 117.49(16) . . ?
F1 C5 C6 119.21(16) . . ?
C4 C5 C6 123.29(17) . . ?
C5 C6 C1 117.00(16) . . ?
C5 C6 C7 127.38(16) . . ?
C1 C6 C7 115.51(15) . . ?
N2 C7 C6 121.24(16) . . ?
N2 C7 C8 114.76(15) . . ?
C6 C7 C8 124.00(15) . . ?
C9 C8 C13 119.28(16) . . ?
C9 C8 C7 121.34(16) . . ?
C13 C8 C7 119.26(15) . . ?
C10 C9 C8 120.04(17) . . ?
C11 C10 C9 120.19(17) . . ?
C10 C11 C12 120.04(17) . . ?
C13 C12 C11 119.84(17) . . ?
C12 C13 C8 120.57(17) . . ?
N1 C14 N2 125.81(16) . . ?
N1 C14 C15 117.28(15) . . ?
N2 C14 C15 116.89(15) . . ?
C16 C15 C20 119.09(16) . . ?
C16 C15 C14 121.00(16) . . ?
C20 C15 C14 119.87(16) . . ?
C17 C16 C15 120.24(17) . . ?
C16 C17 C18 120.44(18) . . ?
C17 C18 C19 119.55(17) . . ?
C20 C19 C18 120.46(18) . . ?
C19 C20 C15 120.22(17) . . ?
C34 N3 C21 116.97(15) . . ?
C27 N4 C34 117.90(15) . . ?
N3 C21 C26 121.94(15) . . ?
N3 C21 C22 118.83(16) . . ?
C26 C21 C22 119.22(15) . . ?
C23 C22 C21 121.00(17) . . ?
C23 C22 Br2 120.27(14) . . ?
C21 C22 Br2 118.73(13) . . ?
C22 C23 C24 120.14(17) . . ?
C25 C24 C23 119.61(16) . . ?
F2 C25 C24 117.59(16) . . ?
F2 C25 C26 119.37(15) . . ?
C24 C25 C26 123.03(17) . . ?
C25 C26 C21 116.90(16) . . ?
C25 C26 C27 127.32(16) . . ?
C21 C26 C27 115.70(15) . . ?
N4 C27 C26 121.06(16) . . ?
N4 C27 C28 114.86(15) . . ?
C26 C27 C28 124.08(15) . . ?
C29 C28 C33 119.42(16) . . ?
C29 C28 C27 121.53(16) . . ?
C33 C28 C27 119.00(15) . . ?
C30 C29 C28 120.25(17) . . ?
C29 C30 C31 119.92(17) . . ?
C32 C31 C30 120.16(17) . . ?
C31 C32 C33 120.05(17) . . ?
C32 C33 C28 120.15(16) . . ?
N3 C34 N4 126.20(16) . . ?
N3 C34 C35 116.95(15) . . ?
N4 C34 C35 116.83(15) . . ?
C40 C35 C36 119.53(16) . . ?
C40 C35 C34 120.78(16) . . ?
C36 C35 C34 119.68(15) . . ?
C37 C36 C35 120.23(17) . . ?
C36 C37 C38 120.04(17) . . ?
C39 C38 C37 119.97(17) . . ?
C38 C39 C40 120.24(17) . . ?
C39 C40 C35 119.97(17) . . ?
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 1.8891(18) . ?
F1 C5 1.348(2) . ?
N1 C14 1.317(2) . ?
N1 C1 1.352(2) . ?
N2 C7 1.318(2) . ?
N2 C14 1.368(2) . ?
C1 C2 1.421(2) . ?
C1 C6 1.427(2) . ?
C2 C3 1.367(3) . ?
C3 C4 1.404(3) . ?
C4 C5 1.366(3) . ?
C5 C6 1.411(2) . ?
C6 C7 1.438(2) . ?
C7 C8 1.491(2) . ?
C8 C9 1.395(2) . ?
C8 C13 1.399(2) . ?
C9 C10 1.392(3) . ?
C10 C11 1.390(3) . ?
C11 C12 1.391(3) . ?
C12 C13 1.386(3) . ?
C14 C15 1.481(2) . ?
C15 C16 1.399(2) . ?
C15 C20 1.401(2) . ?
C16 C17 1.388(3) . ?
C17 C18 1.389(3) . ?
C18 C19 1.392(3) . ?
C19 C20 1.386(3) . ?
Br2 C22 1.8857(18) . ?
F2 C25 1.351(2) . ?
N3 C34 1.317(2) . ?
N3 C21 1.354(2) . ?
N4 C27 1.327(2) . ?
N4 C34 1.363(2) . ?
C21 C26 1.424(2) . ?
C21 C22 1.424(2) . ?
C22 C23 1.367(3) . ?
C23 C24 1.402(3) . ?
C24 C25 1.359(3) . ?
C25 C26 1.415(2) . ?
C26 C27 1.432(2) . ?
C27 C28 1.488(2) . ?
C28 C29 1.396(2) . ?
C28 C33 1.397(2) . ?
C29 C30 1.390(3) . ?
C30 C31 1.391(3) . ?
C31 C32 1.388(3) . ?
C32 C33 1.390(2) . ?
C34 C35 1.480(2) . ?
C35 C40 1.398(2) . ?
C35 C36 1.398(2) . ?
C36 C37 1.390(3) . ?
C37 C38 1.391(3) . ?
C38 C39 1.391(3) . ?
C39 C40 1.392(2) . ?
