<i>ortho</i>-Lithiation driven one-pot synthesis of quinazolines <i>via</i> [2 + 2 + 2] cascade annulation of halofluorobenzenes with nitriles.
Hsueh, Jen-Chun; Szu, Fu-En; Yu, Yin-Yin; Leung, Man-Kit; Organic & biomolecular chemistry 21 (2023) 5297–5304; doi:10.1039/d3ob00741c

data_7159403
_publ_section_title
;
 <i>ortho</i>-Lithiation driven one-pot synthesis of quinazolines
 <i>via</i> [2 + 2 + 2] cascade annulation of halofluorobenzenes with
 nitriles.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; 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'
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_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)
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_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       '\w and \f scans'
_diffrn_radiation_type           CuK\a
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_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.983
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_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
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_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
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_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/[\s^2^(Fo^2^)+(0.0367P)^2^+1.0146P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_estimated_absorpt_t_min   0.447
_shelx_estimated_absorpt_t_max   0.831
_shelx_res_checksum              3018