#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:25:13 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258027 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/08/7240810.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_7240810
loop_
_publ_author_name
'Cui, Luxia'
'Ono, Toshikazu'
'Hossain, Md. Jakir'
'Hisaeda, Yoshio'
_publ_section_title
;
 Electrochemically driven, cobalt--carbon bond-mediated direct
 intramolecular cyclic and acyclic perfluoroalkylation of (hetero)arenes
 using X(CF2)4X
;
_journal_issue                   42
_journal_name_full               'RSC Advances'
_journal_page_first              24862
_journal_page_last               24866
_journal_paper_doi               10.1039/D0RA05295G
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         '0.5(C26 H14 F16 N2)'
_chemical_formula_sum            'C13 H7 F8 N'
_chemical_formula_weight         329.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-09
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_audit_update_record
;
2020-05-18 deposited with the CCDC.	2020-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1069(9)
_cell_length_b                   6.8506(6)
_cell_length_c                   13.7875(12)
_cell_measurement_reflns_used    1706
_cell_measurement_temperature    123
_cell_measurement_theta_max      29.1940
_cell_measurement_theta_min      3.2580
_cell_volume                     1237.98(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   65.00    --   30.00  54.00 -30.00  193
  2  ω    -74.00 119.00   1.00   65.00    --   30.00  54.00 -30.00  193
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0055181000
_diffrn_orient_matrix_UB_12      -0.0065695000
_diffrn_orient_matrix_UB_13      0.0510798000
_diffrn_orient_matrix_UB_21      -0.0536812000
_diffrn_orient_matrix_UB_22      -0.0072805000
_diffrn_orient_matrix_UB_23      0.0050021000
_diffrn_orient_matrix_UB_31      0.0034910000
_diffrn_orient_matrix_UB_32      -0.1031355000
_diffrn_orient_matrix_UB_33      -0.0036259000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8233
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.955
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32e (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1376
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0313
_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)+(0.0520P)²+0.2960P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1121
_reflns_number_total             1376
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra05295g2.cif
_cod_data_source_block           7a
_cod_depositor_comments
'Adding full bibliography for 7240808--7240811.cif.'
_cod_database_code               7240810
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N F'
_chemical_oxdiff_usercomment     'Cui methylindole Cyclicperfluoroalkylation'
_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.
;
_diffrn_oxdiff_ac3_digest_frames
;
01b263afbe41efe93db275c1d0ebd0a7a600386f4cd
;
_diffrn_oxdiff_ac3_digest_hkl
;
01c50784b16bcf86964afc2c1b772243b53fbc
;
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Uiso/Uaniso restraints and constraints
F8 \\sim C7 \\sim C8 \\sim C10 \\sim C13 \\sim F1 \\sim F4 \\sim F6 \\sim C12
\\sim C11 \\sim F7 \\sim F5 \\sim F2 \\sim F3 \\sim C8 \\sim C7 \\sim C13 \\sim
C8 \\sim C10 \\sim C7 \\sim F7 \\sim C13 \\sim F8 \\sim C13 \\sim C12 \\sim C13
\\sim F1 \\sim C10 \\sim F2 \\sim C10 \\sim C11 \\sim C10 \\sim F6 \\sim C12
\\sim C12 \\sim C11 \\sim F5 \\sim C12 \\sim F4 \\sim C11 \\sim F3 \\sim C11:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: F8(0.5) C10(0.5) F1(0.5) H9A(0.5) H9B(0.5) H9C(0.5) F4(0.5)
 F6(0.5) C12(0.5) C11(0.5) F7(0.5) F5(0.5) F2(0.5) F3(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C3(H3), C4(H4)
4.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.143
_oxdiff_exptl_absorpt_empirical_full_min 0.883
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
N1 N 0.60207(11) 0.250000 0.38539(10) 0.0225(3) Uani 1 2 d S T P A .
F8 F 0.81408(18) 0.4410(4) 0.34589(17) 0.0398(5) Uani 0.5 1 d . U . A -1
C7 C 0.67945(13) 0.250000 0.53090(12) 0.0196(4) Uani 1 2 d S TU P . .
C8 C 0.69404(13) 0.250000 0.43207(13) 0.0199(4) Uani 1 2 d S TU P A .
C1 C 0.52636(13) 0.250000 0.45527(13) 0.0215(4) Uani 1 2 d S T P . .
C6 C 0.57211(14) 0.250000 0.54772(13) 0.0209(4) Uani 1 2 d S T P . .
C2 C 0.42008(14) 0.250000 0.44328(15) 0.0275(4) Uani 1 2 d S T P . .
H2 H 0.389753 0.250000 0.380692 0.033 Uiso 1 2 calc RS T P . .
C10 C 0.76314(17) 0.238(5) 0.60211(16) 0.025(2) Uani 0.5 1 d . U . A -1
C13 C 0.79529(14) 0.250000 0.38363(13) 0.0280(4) Uani 1 2 d S TU P . .
C5 C 0.51042(16) 0.250000 0.63123(14) 0.0290(4) Uani 1 2 d S T P . .
H5 H 0.539780 0.250000 0.694221 0.035 Uiso 1 2 calc RS T P A .
F1 F 0.74533(16) 0.3621(4) 0.67857(14) 0.0429(5) Uani 0.5 1 d . U . A -1
C3 C 0.36181(15) 0.250000 0.52611(16) 0.0322(5) Uani 1 2 d S T P . .
H3 H 0.289570 0.250000 0.520513 0.039 Uiso 1 2 calc RS T P A .
C9 C 0.58302(16) 0.250000 0.28098(13) 0.0338(5) Uani 1 2 d S T P . .
H9A H 0.526095 0.337933 0.266317 0.051 Uiso 0.5 1 calc GR . . A -1
H9B H 0.565875 0.117469 0.259757 0.051 Uiso 0.5 1 calc GR . . A -1
H9C H 0.644308 0.294598 0.246823 0.051 Uiso 0.5 1 calc GR . . A -1
C4 C 0.40616(16) 0.250000 0.61884(16) 0.0338(5) Uani 1 2 d S T P A .
H4 H 0.363209 0.250000 0.674347 0.041 Uiso 1 2 calc RS T P . .
F4 F 0.86762(14) 0.4967(2) 0.54544(13) 0.0379(4) Uani 0.5 1 d . U . A -1
F6 F 0.88346(13) 0.0124(3) 0.46667(13) 0.0379(4) Uani 0.5 1 d . U . A -1
C12 C 0.88081(18) 0.2085(4) 0.45604(18) 0.0294(10) Uani 0.5 1 d . U . A -1
C11 C 0.86552(19) 0.3003(4) 0.55569(18) 0.0290(8) Uani 0.5 1 d . U . A -1
F7 F 0.80283(18) 0.1347(4) 0.30804(15) 0.0420(6) Uani 0.5 1 d . U . A -1
F5 F 0.97120(10) 0.235(8) 0.41891(11) 0.043(4) Uani 0.5 1 d . U . A -1
F2 F 0.77493(16) 0.0612(3) 0.64272(15) 0.0398(5) Uani 0.5 1 d . U . A -1
F3 F 0.94357(11) 0.264(8) 0.61452(11) 0.039(4) Uani 0.5 1 d . U . A -1
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
C8 N1 C1 107.74(14) . . ?
C8 N1 C9 127.94(15) . . ?
C1 N1 C9 124.31(15) . . ?
C8 C7 C6 107.35(15) . . ?
C8 C7 C10 123.78(17) . . ?
C6 C7 C10 128.73(18) . . ?
N1 C8 C7 110.12(15) . . ?
N1 C8 C13 125.18(16) . . ?
C7 C8 C13 124.70(16) . . ?
N1 C1 C6 108.97(15) . . ?
N1 C1 C2 129.08(17) . . ?
C2 C1 C6 121.96(17) . . ?
C1 C6 C7 105.83(15) . . ?
C5 C6 C7 134.44(17) . . ?
C5 C6 C1 119.73(17) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 C1 117.00(18) . . ?
C3 C2 H2 121.5 . . ?
C7 C10 C11 110.7(7) . . ?
F1 C10 C7 110.4(13) . . ?
F1 C10 C11 107.1(16) . . ?
F2 C10 C7 114.5(18) . . ?
F2 C10 F1 104.9(6) . . ?
F2 C10 C11 108.8(11) . . ?
F8 C13 C8 108.51(12) . . ?
F8 C13 C12 106.38(17) . . ?
C8 C13 C12 111.19(16) . . ?
F7 C13 F8 104.4(2) . . ?
F7 C13 C8 115.12(16) . . ?
F7 C13 C12 110.61(17) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 C6 117.96(19) . . ?
C4 C5 H5 121.0 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.78(18) . . ?
C4 C3 H3 119.1 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C4 C3 121.57(18) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
F6 C12 C13 105.95(19) . . ?
F6 C12 C11 108.4(2) . . ?
C11 C12 C13 114.6(2) . . ?
F5 C12 C13 112.6(7) . . ?
F5 C12 F6 99(2) . . ?
F5 C12 C11 114.6(13) . . ?
F4 C11 C10 109.6(12) . . ?
F4 C11 C12 108.3(2) . . ?
C12 C11 C10 111.9(7) . . ?
F3 C11 C10 111.3(10) . . ?
F3 C11 F4 104(2) . . ?
F3 C11 C12 111.8(13) . . ?
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
N1 C8 1.367(2) . ?
N1 C1 1.383(2) . ?
N1 C9 1.461(2) . ?
F8 C13 1.430(2) . ?
C7 C8 1.376(2) . ?
C7 C6 1.426(2) . ?
C7 C10 1.474(3) . ?
C8 C13 1.486(2) . ?
C1 C6 1.409(3) . ?
C1 C2 1.403(3) . ?
C6 C5 1.407(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.374(3) . ?
C10 F1 1.38(2) . ?
C10 C11 1.547(10) . ?
C10 F2 1.34(3) . ?
C13 C12 1.528(3) . ?
C13 F7 1.311(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.377(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.404(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C4 H4 0.9500 . ?
F4 C11 1.353(3) . ?
F6 C12 1.351(3) . ?
C12 C11 1.524(4) . ?
C12 F5 1.303(8) . ?
C11 F3 1.329(11) . ?
