#------------------------------------------------------------------------------
#$Date: 2020-11-06 15:13:06 +0200 (Fri, 06 Nov 2020) $
#$Revision: 258972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/76/7157690.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_7157690
loop_
_publ_author_name
'Chan, Chieh-Kai'
'Lai, Chien-Yu'
'Wang, Cheng-Chung'
_publ_section_title
;
 TMSOTf-catalyzed synthesis of substituted quinazolines using
 hexamethyldisilazane as a nitrogen source under neat and microwave
 irradiation conditions.
;
_journal_issue                   36
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7201
_journal_page_last               7212
_journal_paper_doi               10.1039/d0ob01507e
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C20 H13 F N2'
_chemical_formula_sum            'C20 H12 F N2'
_chemical_formula_weight         299.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-04-10 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.8600(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3439(4)
_cell_length_b                   6.8286(2)
_cell_length_c                   20.1913(7)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.07
_cell_measurement_theta_min      3.41
_cell_volume                     1412.80(8)
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            44058
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         3.152
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.9713
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.168
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3120
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0413
_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)+(0.0524P)²+0.7391P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1140
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2704
_reflns_number_total             3120
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01507e2.cif
_cod_data_source_block           i17855
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157689--7157694.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7157690
_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   0.970
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.58228(11) 0.82153(19) 0.32227(5) 0.0261(3) Uani 0.6615(15) 1 d . . P A 1
F1' F 0.9157(2) 0.8819(4) 0.48706(11) 0.0261(3) Uani 0.3385(15) 1 d . . P A 2
N1 N 0.55348(10) 0.73621(16) 0.61485(5) 0.0173(2) Uani 1 1 d . . . . .
N2 N 0.37320(10) 0.70081(15) 0.52792(5) 0.0170(2) Uani 1 1 d . . . . .
C1 C 0.49681(12) 0.73406(17) 0.54954(6) 0.0164(3) Uani 1 1 d . . . . .
C2 C 0.47782(12) 0.70644(18) 0.66145(6) 0.0163(3) Uani 1 1 d . . . . .
C3 C 0.34035(12) 0.67511(18) 0.64478(6) 0.0163(3) Uani 1 1 d . . . . .
C4 C 0.25007(12) 0.6532(2) 0.69119(6) 0.0199(3) Uani 1 1 d . . . . .
H4 H 0.279452 0.661831 0.737774 0.024 Uiso 1 1 calc R U . . .
C5 C 0.12078(13) 0.6195(2) 0.66922(6) 0.0213(3) Uani 1 1 d . . . . .
H5 H 0.061516 0.601221 0.700721 0.026 Uiso 1 1 calc R U . . .
C6 C 0.07499(12) 0.6118(2) 0.60022(7) 0.0214(3) Uani 1 1 d . . . . .
H6 H -0.014823 0.587578 0.585613 0.026 Uiso 1 1 calc R U . . .
C7 C 0.15870(12) 0.63894(19) 0.55413(6) 0.0196(3) Uani 1 1 d . . . . .
H7 H 0.126487 0.636421 0.507764 0.024 Uiso 1 1 calc R U . . .
C8 C 0.29329(12) 0.67078(18) 0.57535(6) 0.0163(3) Uani 1 1 d . . . . .
C9 C 0.58623(12) 0.77303(18) 0.49948(6) 0.0175(3) Uani 1 1 d . . . . .
C10 C 0.53802(13) 0.77793(19) 0.43141(6) 0.0197(3) Uani 1 1 d . . . . .
H10 H 0.448070 0.755489 0.416591 0.024 Uiso 1 1 calc R U . . .
C11 C 0.62316(14) 0.8159(2) 0.38609(7) 0.0240(3) Uani 1 1 d . . . . .
C12 C 0.75434(14) 0.8500(2) 0.40493(7) 0.0244(3) Uani 1 1 d . . . . .
H12 H 0.810909 0.875905 0.372659 0.029 Uiso 1 1 calc R U . . .
C13 C 0.80080(14) 0.8451(2) 0.47262(7) 0.0249(3) Uani 1 1 d . . . . .
C14 C 0.71863(13) 0.80681(19) 0.51986(6) 0.0206(3) Uani 1 1 d . . . . .
H14 H 0.752469 0.803609 0.566020 0.025 Uiso 1 1 calc R U . . .
C15 C 0.54440(12) 0.71282(19) 0.73168(6) 0.0178(3) Uani 1 1 d . . . . .
C16 C 0.63701(12) 0.8585(2) 0.75005(6) 0.0210(3) Uani 1 1 d . . . . .
H16 H 0.656985 0.951239 0.717877 0.025 Uiso 1 1 calc R U . . .
C17 C 0.70016(13) 0.8682(2) 0.81540(7) 0.0245(3) Uani 1 1 d . . . . .
H17 H 0.762067 0.968913 0.827942 0.029 Uiso 1 1 calc R U . . .
C18 C 0.67281(13) 0.7308(2) 0.86237(6) 0.0254(3) Uani 1 1 d . . . . .
H18 H 0.715577 0.737922 0.907039 0.030 Uiso 1 1 calc R U . . .
C19 C 0.58296(12) 0.5834(2) 0.84383(6) 0.0238(3) Uani 1 1 d . . . . .
H19 H 0.565139 0.488370 0.875731 0.029 Uiso 1 1 calc R U . . .
C20 C 0.51892(12) 0.5742(2) 0.77881(6) 0.0208(3) Uani 1 1 d . . . . .
H20 H 0.457435 0.472826 0.766424 0.025 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 0.0033 0.0016 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
C2 N1 C1 117.91(10) . . ?
C1 N2 C8 116.67(10) . . ?
N2 C1 N1 126.27(11) . . ?
N2 C1 C9 118.28(11) . . ?
N1 C1 C9 115.45(11) . . ?
N1 C2 C3 121.48(11) . . ?
N1 C2 C15 115.61(11) . . ?
C3 C2 C15 122.89(11) . . ?
C4 C3 C8 118.83(11) . . ?
C4 C3 C2 125.66(11) . . ?
C8 C3 C2 115.50(11) . . ?
C5 C4 C3 120.38(11) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.50(12) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 120.59(12) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.17(11) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
N2 C8 C7 118.42(11) . . ?
N2 C8 C3 122.10(11) . . ?
C7 C8 C3 119.46(11) . . ?
C14 C9 C10 119.37(12) . . ?
C14 C9 C1 120.47(11) . . ?
C10 C9 C1 120.16(11) . . ?
C11 C10 C9 118.89(12) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
F1 C11 C12 116.29(12) . . ?
F1 C11 C10 120.83(13) . . ?
C12 C11 C10 122.88(13) . . ?
C11 C12 C13 117.63(12) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 H12 121.2 . . ?
F1' C13 C12 115.41(15) . . ?
F1' C13 C14 123.19(16) . . ?
C12 C13 C14 121.36(13) . . ?
C13 C14 C9 119.87(12) . . ?
C13 C14 H14 120.1 . . ?
C9 C14 H14 120.1 . . ?
C20 C15 C16 119.34(11) . . ?
C20 C15 C2 121.63(11) . . ?
C16 C15 C2 119.01(11) . . ?
C17 C16 C15 120.15(12) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 120.11(13) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 119.82(12) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.25(12) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 120.31(12) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
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 1.3006(17) . ?
F1' C13 1.211(3) . ?
N1 C2 1.3193(16) . ?
N1 C1 1.3681(15) . ?
N2 C1 1.3131(16) . ?
N2 C8 1.3633(16) . ?
C1 C9 1.4844(17) . ?
C2 C3 1.4319(17) . ?
C2 C15 1.4899(16) . ?
C3 C4 1.4184(17) . ?
C3 C8 1.4201(16) . ?
C4 C5 1.3695(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.4099(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.3678(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.4163(17) . ?
C7 H7 0.9500 . ?
C9 C14 1.3943(18) . ?
C9 C10 1.3970(17) . ?
C10 C11 1.3786(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(2) . ?
C12 C13 1.386(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3864(18) . ?
C14 H14 0.9500 . ?
C15 C20 1.3929(18) . ?
C15 C16 1.3957(18) . ?
C16 C17 1.3915(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.3887(17) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
