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#$Date: 2023-10-27 00:56:05 +0300 (Fri, 27 Oct 2023) $
#$Revision: 287126 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/22/7132268.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_7132268
loop_
_publ_author_name
'Gao, Qinghe'
'Guo, Yimei'
'Cao, Penghui'
'Fan, Guangping'
'Xu, Yongtao'
_publ_section_title
;
 Regioselective synthesis of indazolo[2,3-a]quinazolines enabled by
 I2/S-facilitated annulation relay dehydrogenative aromatization of
 cyclohexanones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04698B
_journal_year                    2023
_chemical_formula_sum            'C21 H12 F3 N3'
_chemical_formula_weight         363.34
_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-2016/6
_audit_update_record
;
2023-09-21 deposited with the CCDC.	2023-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                97.386(6)
_cell_angle_beta                 107.310(6)
_cell_angle_gamma                93.704(6)
_cell_formula_units_Z            2
_cell_length_a                   9.105(4)
_cell_length_b                   9.483(4)
_cell_length_c                   10.167(4)
_cell_measurement_reflns_used    979
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.06
_cell_measurement_theta_min      2.80
_cell_volume                     826.2(6)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.970
_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  0.0247
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5161
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         2.124
_exptl_absorpt_coefficient_mu    0.112
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0612
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1736
_refine_ls_wR_factor_ref         0.2055
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2180
_reflns_number_total             3685
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc04698b2.cif
_cod_data_source_block           H311_0m
_cod_database_code               7132268
_shelx_shelxl_version_number     2016/6
_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   0.980
_shelx_estimated_absorpt_t_max   0.983
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
F1 F 0.7103(3) 1.1780(2) 0.0743(2) 0.1073(8) Uani 1 1 d . . . . .
F2 F 0.9289(3) 1.1011(2) 0.1142(3) 0.1299(10) Uani 1 1 d . . . . .
F3 F 0.7625(3) 1.0423(2) -0.0824(2) 0.1079(8) Uani 1 1 d . . . . .
N1 N 0.6940(2) 0.5015(2) 0.3191(2) 0.0499(5) Uani 1 1 d . . . . .
N2 N 0.5140(2) 0.3433(2) 0.3767(2) 0.0450(5) Uani 1 1 d . . . . .
N3 N 0.5049(2) 0.2292(2) 0.4428(2) 0.0510(6) Uani 1 1 d . . . . .
C1 C 0.2949(3) 0.6004(3) 0.1836(3) 0.0535(7) Uani 1 1 d . . . . .
H1 H 0.312200 0.678510 0.141352 0.064 Uiso 1 1 calc R U . . .
C2 C 0.1465(3) 0.5549(3) 0.1782(3) 0.0607(7) Uani 1 1 d . . . . .
H2 H 0.064489 0.602306 0.132776 0.073 Uiso 1 1 calc R U . . .
C3 C 0.1188(3) 0.4385(3) 0.2403(3) 0.0606(7) Uani 1 1 d . . . . .
H3 H 0.018096 0.409368 0.236980 0.073 Uiso 1 1 calc R U . . .
C4 C 0.2378(3) 0.3650(3) 0.3071(3) 0.0566(7) Uani 1 1 d . . . . .
H4 H 0.218536 0.286226 0.347652 0.068 Uiso 1 1 calc R U . . .
C5 C 0.3881(3) 0.4122(2) 0.3119(2) 0.0447(6) Uani 1 1 d . . . . .
C6 C 0.4208(3) 0.5311(2) 0.2518(2) 0.0459(6) Uani 1 1 d . . . . .
C7 C 0.5812(3) 0.5721(3) 0.2598(3) 0.0465(6) Uani 1 1 d . . . . .
C8 C 0.6226(3) 0.6983(3) 0.2006(2) 0.0462(6) Uani 1 1 d . . . . .
C9 C 0.5913(3) 0.8334(3) 0.2450(3) 0.0561(7) Uani 1 1 d . . . . .
H9 H 0.535560 0.845186 0.308195 0.067 Uiso 1 1 calc R U . . .
C10 C 0.6419(3) 0.9519(3) 0.1967(3) 0.0603(7) Uani 1 1 d . . . . .
H10 H 0.621408 1.042619 0.228676 0.072 Uiso 1 1 calc R U . . .
C11 C 0.7219(3) 0.9357(3) 0.1019(3) 0.0533(7) Uani 1 1 d . . . . .
C12 C 0.7547(4) 0.8002(3) 0.0564(3) 0.0680(8) Uani 1 1 d . . . . .
H12 H 0.809958 0.788592 -0.007075 0.082 Uiso 1 1 calc R U . . .
C13 C 0.7050(3) 0.6829(3) 0.1056(3) 0.0607(7) Uani 1 1 d . . . . .
H13 H 0.727052 0.592446 0.074799 0.073 Uiso 1 1 calc R U . . .
C14 C 0.7805(4) 1.0616(4) 0.0519(4) 0.0723(9) Uani 1 1 d . . . . .
C15 C 0.6625(3) 0.3886(2) 0.3791(2) 0.0459(6) Uani 1 1 d . . . . .
C16 C 0.7578(3) 0.2979(2) 0.4538(2) 0.0461(6) Uani 1 1 d . . . . .
C17 C 0.6567(3) 0.2026(2) 0.4905(2) 0.0477(6) Uani 1 1 d . . . . .
C18 C 0.7155(3) 0.0943(3) 0.5687(3) 0.0558(7) Uani 1 1 d . . . . .
H18 H 0.649754 0.030486 0.593036 0.067 Uiso 1 1 calc R U . . .
C19 C 0.8676(3) 0.0861(3) 0.6066(3) 0.0627(8) Uani 1 1 d . . . . .
H19 H 0.907397 0.014964 0.657595 0.075 Uiso 1 1 calc R U . . .
C20 C 0.9714(3) 0.1828(3) 0.5716(3) 0.0651(8) Uani 1 1 d . . . . .
H20 H 1.076848 0.173845 0.600722 0.078 Uiso 1 1 calc R U . . .
C21 C 0.9187(3) 0.2875(3) 0.4965(3) 0.0591(7) Uani 1 1 d . . . . .
H21 H 0.986492 0.350626 0.473717 0.071 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'
N N 0.0061 0.0033 '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'
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 C15 118.9(2) . . ?
N3 N2 C15 114.2(2) . . ?
N3 N2 C5 124.5(2) . . ?
C15 N2 C5 121.4(2) . . ?
N2 N3 C17 102.52(19) . . ?
C2 C1 C6 121.1(3) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 118.1(3) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
N2 C5 C4 121.5(2) . . ?
N2 C5 C6 116.3(2) . . ?
C4 C5 C6 122.2(2) . . ?
C1 C6 C5 117.1(2) . . ?
C1 C6 C7 124.1(2) . . ?
C5 C6 C7 118.7(2) . . ?
N1 C7 C6 122.3(2) . . ?
N1 C7 C8 116.8(2) . . ?
C6 C7 C8 121.0(2) . . ?
C9 C8 C13 118.7(2) . . ?
C9 C8 C7 121.6(2) . . ?
C13 C8 C7 119.5(2) . . ?
C8 C9 C10 120.8(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 119.6(2) . . ?
C10 C11 C14 120.9(3) . . ?
C12 C11 C14 119.4(3) . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
F3 C14 F2 105.9(3) . . ?
F3 C14 F1 105.0(3) . . ?
F2 C14 F1 105.1(3) . . ?
F3 C14 C11 114.2(3) . . ?
F2 C14 C11 112.9(3) . . ?
F1 C14 C11 113.0(3) . . ?
N1 C15 N2 122.5(2) . . ?
N1 C15 C16 131.9(2) . . ?
N2 C15 C16 105.7(2) . . ?
C15 C16 C17 104.8(2) . . ?
C15 C16 C21 134.8(2) . . ?
C17 C16 C21 120.4(2) . . ?
N3 C17 C16 112.8(2) . . ?
N3 C17 C18 127.0(2) . . ?
C16 C17 C18 120.2(2) . . ?
C19 C18 C17 118.2(3) . . ?
C19 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
C18 C19 C20 122.2(3) . . ?
C18 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C21 C20 C19 121.1(3) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C16 117.9(3) . . ?
C20 C21 H21 121.0 . . ?
C16 C21 H21 121.0 . . ?
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 C14 1.339(4) . ?
F2 C14 1.315(4) . ?
F3 C14 1.313(4) . ?
N1 C7 1.300(3) . ?
N1 C15 1.354(3) . ?
N2 N3 1.355(3) . ?
N2 C15 1.384(3) . ?
N2 C5 1.391(3) . ?
N3 C17 1.374(3) . ?
C1 C2 1.375(4) . ?
C1 C6 1.403(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.385(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.405(3) . ?
C6 C7 1.462(3) . ?
C7 C8 1.483(3) . ?
C8 C9 1.379(4) . ?
C8 C13 1.387(4) . ?
C9 C10 1.389(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(4) . ?
C11 C14 1.485(4) . ?
C12 C13 1.380(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C15 C16 1.394(3) . ?
C16 C17 1.409(3) . ?
C16 C21 1.413(4) . ?
C17 C18 1.415(4) . ?
C18 C19 1.333(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.425(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.356(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N2 N3 C17 0.7(2) . . . . ?
C5 N2 N3 C17 -178.9(2) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
N3 N2 C5 C4 -1.7(4) . . . . ?
C15 N2 C5 C4 178.7(2) . . . . ?
N3 N2 C5 C6 178.45(19) . . . . ?
C15 N2 C5 C6 -1.1(3) . . . . ?
C3 C4 C5 N2 -179.7(2) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
C2 C1 C6 C7 179.0(2) . . . . ?
N2 C5 C6 C1 178.8(2) . . . . ?
C4 C5 C6 C1 -1.0(4) . . . . ?
N2 C5 C6 C7 0.7(3) . . . . ?
C4 C5 C6 C7 -179.1(2) . . . . ?
C15 N1 C7 C6 -2.0(4) . . . . ?
C15 N1 C7 C8 177.6(2) . . . . ?
C1 C6 C7 N1 -177.1(2) . . . . ?
C5 C6 C7 N1 0.8(4) . . . . ?
C1 C6 C7 C8 3.3(4) . . . . ?
C5 C6 C7 C8 -178.8(2) . . . . ?
N1 C7 C8 C9 -120.9(3) . . . . ?
C6 C7 C8 C9 58.7(3) . . . . ?
N1 C7 C8 C13 54.3(3) . . . . ?
C6 C7 C8 C13 -126.1(3) . . . . ?
C13 C8 C9 C10 -0.4(4) . . . . ?
C7 C8 C9 C10 174.8(2) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C9 C10 C11 C12 -1.2(4) . . . . ?
C9 C10 C11 C14 -178.4(3) . . . . ?
C10 C11 C12 C13 0.7(4) . . . . ?
C14 C11 C12 C13 178.0(3) . . . . ?
C11 C12 C13 C8 -0.1(4) . . . . ?
C9 C8 C13 C12 0.0(4) . . . . ?
C7 C8 C13 C12 -175.4(2) . . . . ?
C10 C11 C14 F3 -138.4(3) . . . . ?
C12 C11 C14 F3 44.4(4) . . . . ?
C10 C11 C14 F2 100.5(4) . . . . ?
C12 C11 C14 F2 -76.7(4) . . . . ?
C10 C11 C14 F1 -18.5(4) . . . . ?
C12 C11 C14 F1 164.3(3) . . . . ?
C7 N1 C15 N2 1.6(3) . . . . ?
C7 N1 C15 C16 -177.0(2) . . . . ?
N3 N2 C15 N1 -179.6(2) . . . . ?
C5 N2 C15 N1 0.0(3) . . . . ?
N3 N2 C15 C16 -0.7(3) . . . . ?
C5 N2 C15 C16 178.9(2) . . . . ?
N1 C15 C16 C17 179.2(2) . . . . ?
N2 C15 C16 C17 0.4(2) . . . . ?
N1 C15 C16 C21 0.5(5) . . . . ?
N2 C15 C16 C21 -178.3(3) . . . . ?
N2 N3 C17 C16 -0.4(3) . . . . ?
N2 N3 C17 C18 179.5(2) . . . . ?
C15 C16 C17 N3 0.0(3) . . . . ?
C21 C16 C17 N3 178.9(2) . . . . ?
C15 C16 C17 C18 -179.9(2) . . . . ?
C21 C16 C17 C18 -1.0(4) . . . . ?
N3 C17 C18 C19 -179.5(2) . . . . ?
C16 C17 C18 C19 0.4(4) . . . . ?
C17 C18 C19 C20 0.3(4) . . . . ?
C18 C19 C20 C21 -0.5(4) . . . . ?
C19 C20 C21 C16 -0.1(4) . . . . ?
C15 C16 C21 C20 179.3(3) . . . . ?
C17 C16 C21 C20 0.8(4) . . . . ?
