#------------------------------------------------------------------------------
#$Date: 2023-06-29 15:21:46 +0200 (Thu 29 de Jun de 2023) $
#$Revision: 284653 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/94/7159403.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_7159403
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                68.5349(18)
_cell_angle_beta                 85.512(2)
_cell_angle_gamma                81.5452(19)
_cell_formula_units_Z            2
_cell_length_a                   4.1687(2)
_cell_length_b                   12.4116(7)
_cell_length_c                   15.8272(9)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.40
_cell_measurement_theta_min      3.00
_cell_volume                     753.56(7)
_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 0.983
_diffrn_measured_fraction_theta_max 0.957
_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  0.0420
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11806
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.430
_diffrn_reflns_theta_min         3.001
_diffrn_source                   'I-mu-S microfocus sealed tube'
_exptl_absorpt_coefficient_mu    3.835
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7584
_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    1.671
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0298
_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)+(0.0367P)²+1.0146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0825
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2837
_reflns_number_total             2948
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00741c2.cif
_cod_data_source_block           ic21767
_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               7159403
_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   0.447
_shelx_estimated_absorpt_t_max   0.831
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 1.09782(6) 0.17568(2) 0.85531(2) 0.02185(10) Uani 1 1 d . . . . .
F1 F 0.9382(4) 0.56570(12) 0.90727(10) 0.0250(3) Uani 1 1 d . . . . .
N1 N 0.4006(5) 0.55209(17) 0.65379(13) 0.0188(4) Uani 1 1 d . . . . .
N2 N 0.3504(5) 0.73561(17) 0.67459(13) 0.0187(4) Uani 1 1 d . . . . .
C1 C 0.2986(6) 0.6649(2) 0.62925(16) 0.0183(5) Uani 1 1 d . . . . .
C2 C 0.5831(6) 0.5026(2) 0.72959(16) 0.0183(5) Uani 1 1 d . . . . .
C3 C 0.7116(6) 0.3841(2) 0.75283(16) 0.0201(5) Uani 1 1 d . . . . .
H3 H 0.664506 0.340917 0.717668 0.024 Uiso 1 1 calc R U . . .
C4 C 0.9044(6) 0.3323(2) 0.82649(16) 0.0196(5) Uani 1 1 d . . . . .
C5 C 0.9770(6) 0.3936(2) 0.88047(16) 0.0200(5) Uani 1 1 d . . . . .
H5 H 1.109891 0.356177 0.931858 0.024 Uiso 1 1 calc R U . . .
C6 C 0.8524(6) 0.5075(2) 0.85712(16) 0.0197(5) Uani 1 1 d . . . . .
C7 C 0.6496(6) 0.5683(2) 0.78183(16) 0.0179(5) Uani 1 1 d . . . . .
C8 C 0.5153(5) 0.6888(2) 0.75053(16) 0.0177(5) Uani 1 1 d . . . . .
C9 C 0.5524(6) 0.7695(2) 0.79832(16) 0.0185(5) Uani 1 1 d . . . . .
C10 C 0.4434(6) 0.7464(2) 0.88827(17) 0.0214(5) Uani 1 1 d . . . . .
H10 H 0.345255 0.677857 0.920328 0.026 Uiso 1 1 calc R U . . .
C11 C 0.4791(6) 0.8242(2) 0.93072(17) 0.0215(5) Uani 1 1 d . . . . .
H11 H 0.401299 0.809297 0.991468 0.026 Uiso 1 1 calc R U . . .
C12 C 0.6271(6) 0.9230(2) 0.88504(17) 0.0213(5) Uani 1 1 d . . . . .
H12 H 0.656049 0.974701 0.914873 0.026 Uiso 1 1 calc R U . . .
C13 C 0.7334(6) 0.9466(2) 0.79549(17) 0.0220(5) Uani 1 1 d . . . . .
H13 H 0.835532 1.014400 0.764201 0.026 Uiso 1 1 calc R U . . .
C14 C 0.6913(6) 0.8716(2) 0.75146(16) 0.0204(5) Uani 1 1 d . . . . .
H14 H 0.756885 0.889676 0.689471 0.024 Uiso 1 1 calc R U . . .
C15 C 0.1045(6) 0.7201(2) 0.54577(16) 0.0193(5) Uani 1 1 d . . . . .
C16 C -0.0056(6) 0.8391(2) 0.51323(17) 0.0221(5) Uani 1 1 d . . . . .
H16 H 0.042138 0.886605 0.544779 0.027 Uiso 1 1 calc R U . . .
C17 C -0.1854(6) 0.8887(2) 0.43464(17) 0.0247(5) Uani 1 1 d . . . . .
H17 H -0.259798 0.969948 0.412598 0.030 Uiso 1 1 calc R U . . .
C18 C -0.2559(6) 0.8196(2) 0.38855(17) 0.0249(5) Uani 1 1 d . . . . .
H18 H -0.379183 0.853542 0.335029 0.030 Uiso 1 1 calc R U . . .
C19 C -0.1474(6) 0.7015(2) 0.42017(17) 0.0244(5) Uani 1 1 d . . . . .
H19 H -0.197129 0.654289 0.388559 0.029 Uiso 1 1 calc R U . . .
C20 C 0.0344(6) 0.6515(2) 0.49827(17) 0.0221(5) Uani 1 1 d . . . . .
H20 H 0.111314 0.570470 0.519373 0.026 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
C1 N1 C2 116.9(2) . . ?
C8 N2 C1 118.5(2) . . ?
N1 C1 N2 125.9(2) . . ?
N1 C1 C15 117.3(2) . . ?
N2 C1 C15 116.8(2) . . ?
N1 C2 C3 117.3(2) . . ?
N1 C2 C7 121.6(2) . . ?
C3 C2 C7 121.1(2) . . ?
C4 C3 C2 119.2(2) . . ?
C3 C4 C5 121.8(2) . . ?
C3 C4 Br1 119.96(18) . . ?
C5 C4 Br1 118.15(18) . . ?
C6 C5 C4 118.2(2) . . ?
F1 C6 C5 117.0(2) . . ?
F1 C6 C7 119.2(2) . . ?
C5 C6 C7 123.7(2) . . ?
C6 C7 C2 116.0(2) . . ?
C6 C7 C8 127.6(2) . . ?
C2 C7 C8 116.4(2) . . ?
N2 C8 C7 120.6(2) . . ?
N2 C8 C9 115.8(2) . . ?
C7 C8 C9 123.6(2) . . ?
C14 C9 C10 119.5(2) . . ?
C14 C9 C8 119.2(2) . . ?
C10 C9 C8 121.2(2) . . ?
C11 C10 C9 119.8(2) . . ?
C12 C11 C10 120.4(2) . . ?
C11 C12 C13 119.9(2) . . ?
C14 C13 C12 120.4(2) . . ?
C13 C14 C9 120.0(2) . . ?
C16 C15 C20 119.2(2) . . ?
C16 C15 C1 121.4(2) . . ?
C20 C15 C1 119.4(2) . . ?
C17 C16 C15 120.2(2) . . ?
C18 C17 C16 120.0(2) . . ?
C19 C18 C17 120.2(2) . . ?
C18 C19 C20 120.1(2) . . ?
C19 C20 C15 120.3(2) . . ?
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 C4 1.893(2) . ?
F1 C6 1.349(3) . ?
N1 C1 1.322(3) . ?
N1 C2 1.364(3) . ?
N2 C8 1.325(3) . ?
N2 C1 1.368(3) . ?
C1 C15 1.487(3) . ?
C2 C3 1.410(3) . ?
C2 C7 1.421(3) . ?
C3 C4 1.366(4) . ?
C4 C5 1.410(3) . ?
C5 C6 1.355(3) . ?
C6 C7 1.420(3) . ?
C7 C8 1.433(3) . ?
C8 C9 1.489(3) . ?
C9 C14 1.397(3) . ?
C9 C10 1.398(3) . ?
C10 C11 1.393(3) . ?
C11 C12 1.382(4) . ?
C12 C13 1.388(4) . ?
C13 C14 1.387(3) . ?
C15 C16 1.392(3) . ?
C15 C20 1.396(3) . ?
C16 C17 1.392(4) . ?
C17 C18 1.386(4) . ?
C18 C19 1.381(4) . ?
C19 C20 1.391(4) . ?
