#------------------------------------------------------------------------------
#$Date: 2022-11-07 07:20:45 +0200 (Mon, 07 Nov 2022) $
#$Revision: 278983 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/76/1567631.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_1567631
loop_
_publ_author_name
'Wang, Gang'
'Li, Wenqi'
'Liu, Tianxiang'
'Zhang, Yonghong'
'Wang, Bin'
'Xue, Fei'
'Jin, Weiwei'
'Ma, Caiyan'
'Xia, Yu'
'Liu, Chenjiang'
_publ_section_title
;
 Palladium-catalyzed intramolecular Heck dearomative
 gem-difluorovinylation of indoles.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              11594
_journal_page_last               11599
_journal_paper_doi               10.1039/d2sc03169h
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C17 H11 F2 N O'
_chemical_formula_sum            'C17 H11 F2 N O'
_chemical_formula_weight         283.27
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_audit_update_record
;
2021-08-03 deposited with the CCDC.	2022-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.631(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.160(4)
_cell_length_b                   7.282(2)
_cell_length_c                   14.200(4)
_cell_measurement_reflns_used    800
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.19
_cell_measurement_theta_min      2.31
_cell_volume                     1341.6(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_av_unetI/netI     0.0903
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6537
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.910
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0561 before and 0.0363 after correction.
The Ratio of minimum to maximum transmission is 0.8710.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2358
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.1363
_refine_ls_R_factor_gt           0.0488
_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)+(0.0356P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.1102
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1140
_reflns_number_total             2358
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc03169h2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 1567630--1567632.cif.'
_cod_database_code               1567631
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.92954(12) 0.6181(2) 0.43924(12) 0.0858(6) Uani 1 1 d . . . . .
F2 F 0.91023(12) 0.6247(2) 0.28551(12) 0.0871(6) Uani 1 1 d . . . . .
O1 O 0.49313(16) 0.2911(3) 0.39618(14) 0.0809(7) Uani 1 1 d . . . . .
N1 N 0.59894(15) 0.5434(3) 0.39120(16) 0.0530(6) Uani 1 1 d . . . . .
C1 C 0.7615(2) 0.6101(4) 0.35459(18) 0.0486(7) Uani 1 1 d . . . . .
C2 C 0.70190(19) 0.6065(4) 0.43911(19) 0.0495(7) Uani 1 1 d . . . . .
C3 C 0.6845(2) 0.6132(4) 0.26744(19) 0.0512(7) Uani 1 1 d . . . . .
C4 C 0.7279(2) 0.4665(4) 0.51823(19) 0.0528(7) Uani 1 1 d . . . . .
C5 C 0.5683(2) 0.3814(4) 0.4298(2) 0.0598(8) Uani 1 1 d . . . . .
C6 C 0.6467(2) 0.3452(4) 0.5151(2) 0.0559(8) Uani 1 1 d . . . . .
C7 C 0.5884(2) 0.5753(4) 0.2910(2) 0.0545(8) Uani 1 1 d . . . . .
C8 C 0.8602(3) 0.6184(4) 0.3598(2) 0.0607(8) Uani 1 1 d . . . . .
C9 C 0.8110(2) 0.4580(4) 0.5920(2) 0.0665(9) Uani 1 1 d . . . . .
H9 H 0.865191 0.540940 0.595390 0.080 Uiso 1 1 calc R U . . .
C10 C 0.6948(2) 0.8000(4) 0.47909(19) 0.0615(8) Uani 1 1 d . . . . .
H10A H 0.665050 0.881135 0.428662 0.092 Uiso 1 1 calc R U . . .
H10B H 0.762538 0.842351 0.505897 0.092 Uiso 1 1 calc R U . . .
H10C H 0.652296 0.797946 0.527842 0.092 Uiso 1 1 calc R U . . .
C11 C 0.4995(2) 0.5680(4) 0.2242(2) 0.0702(9) Uani 1 1 d . . . . .
H11 H 0.435781 0.543052 0.241542 0.084 Uiso 1 1 calc R U . . .
C12 C 0.6919(3) 0.6448(4) 0.1722(2) 0.0649(8) Uani 1 1 d . . . . .
H12 H 0.755328 0.669533 0.154367 0.078 Uiso 1 1 calc R U . . .
C13 C 0.6461(3) 0.2100(4) 0.5840(3) 0.0774(10) Uani 1 1 d . . . . .
H13 H 0.591137 0.128755 0.581379 0.093 Uiso 1 1 calc R U . . .
C14 C 0.8114(3) 0.3229(5) 0.6605(2) 0.0809(10) Uani 1 1 d . . . . .
H14 H 0.867316 0.314112 0.709964 0.097 Uiso 1 1 calc R U . . .
C15 C 0.7304(3) 0.2008(5) 0.6570(2) 0.0858(11) Uani 1 1 d . . . . .
H15 H 0.732533 0.111397 0.704102 0.103 Uiso 1 1 calc R U . . .
C16 C 0.5098(3) 0.6000(4) 0.1295(2) 0.0825(10) Uani 1 1 d . . . . .
H16 H 0.451626 0.594760 0.082281 0.099 Uiso 1 1 calc R U . . .
C17 C 0.6032(3) 0.6388(4) 0.1044(2) 0.0764(10) Uani 1 1 d . . . . .
H17 H 0.607277 0.661652 0.040738 0.092 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'
O O 0.0106 0.0060 '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
C5 N1 C2 112.7(2) . . ?
C5 N1 C7 123.1(2) . . ?
C7 N1 C2 109.6(2) . . ?
C3 C1 C2 106.7(2) . . ?
C8 C1 C2 126.6(3) . . ?
C8 C1 C3 126.6(3) . . ?
N1 C2 C1 101.1(2) . . ?
N1 C2 C4 102.0(2) . . ?
N1 C2 C10 110.4(2) . . ?
C4 C2 C1 120.6(2) . . ?
C4 C2 C10 111.4(2) . . ?
C10 C2 C1 110.2(2) . . ?
C7 C3 C1 108.8(2) . . ?
C7 C3 C12 118.8(3) . . ?
C12 C3 C1 132.4(3) . . ?
C6 C4 C2 109.3(2) . . ?
C6 C4 C9 120.3(3) . . ?
C9 C4 C2 130.1(3) . . ?
O1 C5 N1 125.1(3) . . ?
O1 C5 C6 129.4(3) . . ?
N1 C5 C6 105.5(3) . . ?
C4 C6 C5 110.0(3) . . ?
C4 C6 C13 121.8(3) . . ?
C13 C6 C5 128.2(3) . . ?
C3 C7 N1 109.4(2) . . ?
C11 C7 N1 127.6(3) . . ?
C11 C7 C3 123.0(3) . . ?
F1 C8 F2 108.2(3) . . ?
C1 C8 F1 126.2(3) . . ?
C1 C8 F2 125.6(3) . . ?
C4 C9 H9 120.8 . . ?
C14 C9 C4 118.3(3) . . ?
C14 C9 H9 120.8 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11 121.7 . . ?
C7 C11 C16 116.7(3) . . ?
C16 C11 H11 121.7 . . ?
C3 C12 H12 120.5 . . ?
C17 C12 C3 118.9(3) . . ?
C17 C12 H12 120.5 . . ?
C6 C13 H13 121.2 . . ?
C15 C13 C6 117.5(3) . . ?
C15 C13 H13 121.2 . . ?
C9 C14 H14 119.3 . . ?
C15 C14 C9 121.3(3) . . ?
C15 C14 H14 119.3 . . ?
C13 C15 H15 119.6 . . ?
C14 C15 C13 120.7(3) . . ?
C14 C15 H15 119.6 . . ?
C11 C16 H16 119.2 . . ?
C17 C16 C11 121.5(3) . . ?
C17 C16 H16 119.2 . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.1(3) . . ?
C16 C17 H17 119.4 . . ?
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 C8 1.327(3) . ?
F2 C8 1.334(3) . ?
O1 C5 1.217(3) . ?
N1 C2 1.484(3) . ?
N1 C5 1.388(3) . ?
N1 C7 1.425(3) . ?
C1 C2 1.540(3) . ?
C1 C3 1.463(3) . ?
C1 C8 1.290(3) . ?
C2 C4 1.513(3) . ?
C2 C10 1.527(3) . ?
C3 C7 1.389(3) . ?
C3 C12 1.391(4) . ?
C4 C6 1.381(4) . ?
C4 C9 1.383(3) . ?
C5 C6 1.477(4) . ?
C6 C13 1.389(4) . ?
C7 C11 1.379(3) . ?
C9 H9 0.9300 . ?
C9 C14 1.383(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C16 1.394(4) . ?
C12 H12 0.9300 . ?
C12 C17 1.383(4) . ?
C13 H13 0.9300 . ?
C13 C15 1.388(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.366(4) . ?
C17 H17 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
O1 C5 C6 C4 169.9(3) . . . . ?
O1 C5 C6 C13 -8.7(5) . . . . ?
N1 C2 C4 C6 -1.7(3) . . . . ?
N1 C2 C4 C9 -175.0(3) . . . . ?
N1 C5 C6 C4 -8.4(3) . . . . ?
N1 C5 C6 C13 172.9(2) . . . . ?
N1 C7 C11 C16 -178.3(3) . . . . ?
C1 C2 C4 C6 -112.4(3) . . . . ?
C1 C2 C4 C9 74.3(4) . . . . ?
C1 C3 C7 N1 -1.1(3) . . . . ?
C1 C3 C7 C11 -179.9(2) . . . . ?
C1 C3 C12 C17 -179.8(3) . . . . ?
C2 N1 C5 O1 -171.0(2) . . . . ?
C2 N1 C5 C6 7.4(3) . . . . ?
C2 N1 C7 C3 14.2(3) . . . . ?
C2 N1 C7 C11 -167.1(3) . . . . ?
C2 C1 C3 C7 -11.7(3) . . . . ?
C2 C1 C3 C12 168.6(3) . . . . ?
C2 C1 C8 F1 2.8(5) . . . . ?
C2 C1 C8 F2 -178.7(3) . . . . ?
C2 C4 C6 C5 6.2(3) . . . . ?
C2 C4 C6 C13 -175.1(2) . . . . ?
C2 C4 C9 C14 174.1(2) . . . . ?
C3 C1 C2 N1 18.8(3) . . . . ?
C3 C1 C2 C4 130.0(2) . . . . ?
C3 C1 C2 C10 -97.9(2) . . . . ?
C3 C1 C8 F1 179.0(2) . . . . ?
C3 C1 C8 F2 -2.6(5) . . . . ?
C3 C7 C11 C16 0.3(4) . . . . ?
C3 C12 C17 C16 -1.0(4) . . . . ?
C4 C6 C13 C15 0.1(4) . . . . ?
C4 C9 C14 C15 -1.1(4) . . . . ?
C5 N1 C2 C1 121.0(2) . . . . ?
C5 N1 C2 C4 -3.8(3) . . . . ?
C5 N1 C2 C10 -122.3(2) . . . . ?
C5 N1 C7 C3 -122.0(3) . . . . ?
C5 N1 C7 C11 56.8(4) . . . . ?
C5 C6 C13 C15 178.5(3) . . . . ?
C6 C4 C9 C14 1.5(4) . . . . ?
C6 C13 C15 C14 0.3(5) . . . . ?
C7 N1 C2 C1 -20.0(3) . . . . ?
C7 N1 C2 C4 -144.9(2) . . . . ?
C7 N1 C2 C10 96.6(2) . . . . ?
C7 N1 C5 O1 -36.0(4) . . . . ?
C7 N1 C5 C6 142.4(2) . . . . ?
C7 C3 C12 C17 0.5(4) . . . . ?
C7 C11 C16 C17 -0.8(5) . . . . ?
C8 C1 C2 N1 -164.4(3) . . . . ?
C8 C1 C2 C4 -53.2(4) . . . . ?
C8 C1 C2 C10 78.8(4) . . . . ?
C8 C1 C3 C7 171.6(3) . . . . ?
C8 C1 C3 C12 -8.1(5) . . . . ?
C9 C4 C6 C5 -179.7(2) . . . . ?
C9 C4 C6 C13 -1.0(4) . . . . ?
C9 C14 C15 C13 0.2(5) . . . . ?
C10 C2 C4 C6 116.1(2) . . . . ?
C10 C2 C4 C9 -57.2(3) . . . . ?
C11 C16 C17 C12 1.1(5) . . . . ?
C12 C3 C7 N1 178.6(2) . . . . ?
C12 C3 C7 C11 -0.2(4) . . . . ?
