#------------------------------------------------------------------------------
#$Date: 2023-06-29 16:21:46 +0300 (Thu, 29 Jun 2023) $
#$Revision: 284653 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/94/7159402.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_7159402
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            'C34 H21 F N4'
_chemical_formula_weight         504.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                90
_cell_angle_beta                 94.5198(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.0446(6)
_cell_length_b                   11.8808(4)
_cell_length_c                   11.2129(4)
_cell_measurement_reflns_used    9866
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.83
_cell_measurement_theta_min      4.46
_cell_volume                     2396.39(14)
_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 0.994
_diffrn_measured_fraction_theta_max 0.974
_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  0.0351
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            28125
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         78.124
_diffrn_reflns_theta_min         4.460
_diffrn_source                   'I-mu-S microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9114
_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    1.398
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2508
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0377
_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)+(0.0612P)²+1.9206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2388
_reflns_number_total             2508
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00741c2.cif
_cod_data_source_block           ic21850
_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      'C 2/c'
_cod_database_code               7159402
_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   0.901
_shelx_estimated_absorpt_t_max   0.932
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
F1 F 0.500000 0.80725(7) 0.750000 0.0235(2) Uani 1 2 d S T P . .
N1 N 0.42108(5) 0.45555(7) 0.57162(7) 0.0157(2) Uani 1 1 d . . . . .
N2 N 0.38287(5) 0.62648(7) 0.47104(8) 0.0159(2) Uani 1 1 d . . . . .
C1 C 0.32179(6) 0.33296(9) 0.41620(10) 0.0188(2) Uani 1 1 d . . . . .
H1A H 0.340873 0.298279 0.488556 0.023 Uiso 1 1 calc R U . . .
C2 C 0.27812(6) 0.27087(9) 0.33194(10) 0.0206(2) Uani 1 1 d . . . . .
H2A H 0.266862 0.194416 0.347536 0.025 Uiso 1 1 calc R U . . .
C3 C 0.25092(6) 0.32073(9) 0.22478(10) 0.0205(2) Uani 1 1 d . . . . .
H3A H 0.221813 0.278184 0.166628 0.025 Uiso 1 1 calc R U . . .
C4 C 0.26673(6) 0.43344(9) 0.20357(9) 0.0191(2) Uani 1 1 d . . . . .
H4A H 0.248333 0.467653 0.130577 0.023 Uiso 1 1 calc R U . . .
C5 C 0.30904(6) 0.49598(9) 0.28803(9) 0.0174(2) Uani 1 1 d . . . . .
H5A H 0.318675 0.573152 0.273369 0.021 Uiso 1 1 calc R U . . .
C6 C 0.33768(6) 0.44592(9) 0.39493(9) 0.0158(2) Uani 1 1 d . . . . .
C7 C 0.38393(6) 0.51129(9) 0.48576(9) 0.0151(2) Uani 1 1 d . . . . .
C8 C 0.46000(5) 0.51790(9) 0.65840(9) 0.0148(2) Uani 1 1 d . . . . .
C9 C 0.45926(5) 0.63869(9) 0.65619(8) 0.0147(2) Uani 1 1 d . . . . .
C10 C 0.500000 0.45988(12) 0.750000 0.0159(3) Uani 1 2 d S T P . .
H10A H 0.500001 0.379914 0.749999 0.019 Uiso 1 2 calc R U P . .
C11 C 0.500000 0.69444(12) 0.750000 0.0161(3) Uani 1 2 d S T P . .
C12 C 0.41828(5) 0.68923(9) 0.55364(9) 0.0149(2) Uani 1 1 d . . . . .
C13 C 0.41356(6) 0.81221(8) 0.52703(9) 0.0154(2) Uani 1 1 d . . . . .
C14 C 0.43835(6) 0.84895(9) 0.41879(9) 0.0179(2) Uani 1 1 d . . . . .
H14A H 0.459806 0.796827 0.367252 0.022 Uiso 1 1 calc R U . . .
C15 C 0.43174(6) 0.96153(9) 0.38627(10) 0.0204(2) Uani 1 1 d . . . . .
H15A H 0.449714 0.986484 0.313400 0.025 Uiso 1 1 calc R U . . .
C16 C 0.39903(6) 1.03754(9) 0.45968(10) 0.0206(2) Uani 1 1 d . . . . .
H16A H 0.395036 1.114625 0.437574 0.025 Uiso 1 1 calc R U . . .
C17 C 0.37210(6) 1.00100(9) 0.56554(10) 0.0199(2) Uani 1 1 d . . . . .
H17A H 0.348348 1.052701 0.614734 0.024 Uiso 1 1 calc R U . . .
C18 C 0.37980(6) 0.88872(9) 0.59986(9) 0.0185(2) Uani 1 1 d . . . . .
H18A H 0.362012 0.864213 0.673039 0.022 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'
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
C7 N1 C8 116.90(9) . . ?
C12 N2 C7 118.50(9) . . ?
C2 C1 C6 120.38(10) . . ?
C1 C2 C3 120.11(10) . . ?
C4 C3 C2 119.51(10) . . ?
C5 C4 C3 120.54(10) . . ?
C4 C5 C6 120.26(10) . . ?
C1 C6 C5 119.18(9) . . ?
C1 C6 C7 119.84(9) . . ?
C5 C6 C7 120.99(9) . . ?
N1 C7 N2 126.30(9) . . ?
N1 C7 C6 117.88(9) . . ?
N2 C7 C6 115.82(9) . . ?
N1 C8 C10 117.58(10) . . ?
N1 C8 C9 121.62(9) . . ?
C10 C8 C9 120.79(9) . . ?
C11 C9 C8 117.13(9) . . ?
C11 C9 C12 127.24(10) . . ?
C8 C9 C12 115.59(9) . . ?
C8 C10 C8 120.57(13) 2_656 . ?
F1 C11 C9 118.20(7) . . ?
F1 C11 C9 118.21(7) . 2_656 ?
C9 C11 C9 123.59(13) . 2_656 ?
N2 C12 C9 120.92(9) . . ?
N2 C12 C13 113.42(9) . . ?
C9 C12 C13 125.63(9) . . ?
C18 C13 C14 119.36(9) . . ?
C18 C13 C12 122.82(9) . . ?
C14 C13 C12 117.57(9) . . ?
C15 C14 C13 120.16(10) . . ?
C16 C15 C14 120.25(10) . . ?
C15 C16 C17 119.93(10) . . ?
C16 C17 C18 120.15(10) . . ?
C17 C18 C13 120.11(10) . . ?
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
F1 C11 1.3404(17) . ?
N1 C7 1.3089(13) . ?
N1 C8 1.3716(13) . ?
N2 C12 1.3149(13) . ?
N2 C7 1.3783(13) . ?
C1 C2 1.3931(14) . ?
C1 C6 1.3967(15) . ?
C2 C3 1.3938(15) . ?
C3 C4 1.3935(16) . ?
C4 C5 1.3849(15) . ?
C5 C6 1.4000(14) . ?
C6 C7 1.4843(14) . ?
C8 C10 1.3909(12) . ?
C8 C9 1.4353(14) . ?
C9 C11 1.4013(12) . ?
C9 C12 1.4476(13) . ?
C12 C13 1.4923(14) . ?
C13 C18 1.3938(14) . ?
C13 C14 1.3963(14) . ?
C14 C15 1.3890(15) . ?
C15 C16 1.3850(16) . ?
C16 C17 1.3873(16) . ?
C17 C18 1.3923(15) . ?
