#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:25:13 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258027 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/08/7240808.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_7240808
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         'C12 H8 F8 O2'
_chemical_formula_sum            'C12 H8 F8 O2'
_chemical_formula_weight         336.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-26
_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                 95.319(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8488(11)
_cell_length_b                   11.665(2)
_cell_length_c                   15.489(2)
_cell_measurement_reflns_used    893
_cell_measurement_temperature    123
_cell_measurement_theta_max      31.6170
_cell_measurement_theta_min      3.4280
_cell_volume                     1232.1(3)
_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_detector_type            'CCD area detector'
_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   95.00    --   30.00  54.00 150.00  193
  2  ω    -74.00 119.00   1.00   95.00    --   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      -0.0063068000
_diffrn_orient_matrix_UB_12      -0.0484319000
_diffrn_orient_matrix_UB_13      0.0273185000
_diffrn_orient_matrix_UB_21      0.0787810000
_diffrn_orient_matrix_UB_22      -0.0260777000
_diffrn_orient_matrix_UB_23      -0.0193533000
_diffrn_orient_matrix_UB_31      0.0676364000
_diffrn_orient_matrix_UB_32      0.0260791000
_diffrn_orient_matrix_UB_33      0.0314880000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0790
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            1947
_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         26.367
_diffrn_reflns_theta_min         2.641
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58936
_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    1.812
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.840
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1947
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.840
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0526
_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)+(0.0840P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1383
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1031
_reflns_number_total             1947
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;
TITL ono065_twin1_hklf4_a.res in I2/a
    ono065_twin1_hklf4.res
    created by SHELXL-2018/3 at 09:32:02 on 26-Nov-2019
REM Old TITL ono065_twin1_hklf4 in I2/a
REM SHELXT solution in I2/a: R1 0.180, Rweak 0.012, Alpha 0.024
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Formula found by SHELXT: C6 O F4
CELL 0.71073 6.8488 11.665 15.4894 90 95.319 90
ZERR 4 0.0011 0.0022 0.0024 0 0.014 0
LATT 2
SYMM 0.5-X,+Y,-Z
SFAC C H F O
UNIT 48 32 32 8

L.S. 10
PLAN  20
TEMP -150.15
BOND
list 4
fmap 2
ACTA
SHEL 999 0.8
REM <olex2.extras>
REM <HklSrc "%.\\ono065_twin1_hklf5.hkl">
REM </olex2.extras>

WGHT    0.084000
BASF   0.32740
FVAR       1.11301
C1    1    0.270464    0.561760    0.544524    11.00000    0.02496    0.02096 =
         0.02321   -0.00444    0.00112   -0.00224
AFIX  43
H1    2    0.283672    0.632479    0.574922    11.00000   -1.20000
AFIX   0
C2    1    0.292223    0.460284    0.589475    11.00000    0.02234    0.02460 =
         0.01658   -0.00280   -0.00064   -0.00065
C3    1    0.273407    0.356634    0.545109    11.00000    0.02274    0.01937 =
         0.01892   -0.00056    0.00088   -0.00036
C4    1    0.306527    0.247357    0.595314    11.00000    0.03299    0.02293 =
         0.01719   -0.00098   -0.00251    0.00187
C5    1    0.326104    0.142098    0.538338    11.00000    0.04036    0.02018 =
         0.02064    0.00432    0.00176   -0.00063
C6    1    0.347851    0.556413    0.725547    11.00000    0.04537    0.02599 =
         0.02155   -0.00781    0.00256   -0.00308
AFIX 137
H6A   2    0.458008    0.601505    0.707750    11.00000   -1.50000
H6B   2    0.370583    0.538472    0.787472    11.00000   -1.50000
H6C   2    0.226381    0.600660    0.714847    11.00000   -1.50000
AFIX   0
F1    3    0.161145    0.227718    0.646623    11.00000    0.05233    0.02880 =
         0.02535    0.00195    0.01415   -0.00192
F2    3    0.475327    0.250764    0.648915    11.00000    0.04365    0.02939 =
         0.02807    0.00172   -0.01209    0.00192
F3    3    0.310460    0.045858    0.585800    11.00000    0.06156    0.01898 =
         0.02678    0.00407   -0.00423    0.00104
F4    3    0.504724    0.142011    0.508938    11.00000    0.03436    0.03449 =
         0.03682   -0.00189   -0.00034    0.00769
O1    4    0.331235    0.452518    0.676901    11.00000    0.04580    0.02244 =
         0.01530   -0.00212   -0.00529   -0.00173
HKLF 5




REM  ono065_twin1_hklf4_a.res in I2/a
REM wR2 = 0.1383, GooF = S = 0.840, Restrained GooF = 0.840 for all data
REM R1 = 0.0526 for 1031 Fo > 4sig(Fo) and 0.0912 for all 1947 data
REM 102 parameters refined using 0 restraints

END  
     
WGHT      0.0839      0.0000 

REM Highest difference peak  0.375,  deepest hole -0.335,  1-sigma level  0.101
Q1    1  -0.0416  0.2521  0.6626  11.00000  0.05    0.37
Q2    1   0.2255  0.7518  0.6247  11.00000  0.05    0.34
Q3    1   0.5006  0.0518  0.5679  11.00000  0.05    0.32
Q4    1   0.5169  0.0221  0.4632  11.00000  0.05    0.29
Q5    1   0.7500  0.1018  0.5000  10.50000  0.05    0.28
Q6    1   0.5007  0.3913  0.6868  11.00000  0.05    0.28
Q7    1   0.0223  0.2483  0.6225  11.00000  0.05    0.28
Q8    1   0.4851  0.3333  0.5202  11.00000  0.05    0.28
Q9    1   0.2293 -0.0363  0.6077  11.00000  0.05    0.28
Q10   1   0.4947  0.5969  0.5350  11.00000  0.05    0.26
Q11   1   0.5157  0.4179  0.5554  11.00000  0.05    0.26
Q12   1   0.5092  0.5048  0.6872  11.00000  0.05    0.26
Q13   1   0.2238  0.2438  0.6279  11.00000  0.05    0.26
Q14   1   0.6265  0.1475  0.4704  11.00000  0.05    0.25
Q15   1   0.7465  0.1811  0.6366  11.00000  0.05    0.24
Q16   1   0.4852  0.5113  0.5365  11.00000  0.05    0.24
Q17   1   0.4867  0.5297  0.7913  11.00000  0.05    0.24
Q18   1   0.2171  0.0535  0.6310  11.00000  0.05    0.23
Q19   1   0.5246  0.5334  0.6170  11.00000  0.05    0.23
Q20   1   0.5114  0.5586  0.6986  11.00000  0.05    0.23

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0526 for 1031 Fo > 4sig(Fo) and 0.0912 for all 3330 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.37, deepest hole -0.34
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0912
  REM R1_gt = 0.0526
  REM wR_ref = 0.1383
  REM GOOF = 0.840
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 3330
  REM Reflections_gt = 1031
  REM Parameters = n/a
  REM Hole = -0.34
  REM Peak = 0.37
  REM Flack = n/a

  
;
_twin_special_details
;
Component 2 rotated by 179.9575° 
 around [0.00 -0.00 1.00] (reciprocal) or [0.20 0.00 0.98] (direct)
;
_cod_data_source_file            d0ra05295g2.cif
_cod_data_source_block           twin_1a
_cod_depositor_comments
'Adding full bibliography for 7240808--7240811.cif.'
_cod_original_cell_volume        1232.1(4)
_cod_database_code               7240808
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O F'
_chemical_oxdiff_usercomment     'Cui 14diMeObenz cyclicperfluoro'
_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
;
013c857432b67a020773a68214c6886bf0003866068
;
_diffrn_oxdiff_ac3_digest_hkl
;
011d3f8515c2ab83db74fd6e918c835049299b
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.673(2)
 0.327(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1)
3.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_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 1.663
_oxdiff_exptl_absorpt_empirical_full_min 0.701
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -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
C1 C 0.2705(5) 0.5618(3) 0.5445(2) 0.0231(9) Uani 1 1 d . . . . .
H1 H 0.283672 0.632479 0.574922 0.028 Uiso 1 1 calc R . . . .
C2 C 0.2922(5) 0.4603(3) 0.5895(2) 0.0213(8) Uani 1 1 d . . . . .
C3 C 0.2734(5) 0.3566(3) 0.5451(2) 0.0204(8) Uani 1 1 d . . . . .
C4 C 0.3065(6) 0.2474(3) 0.5953(2) 0.0247(9) Uani 1 1 d . . . . .
C5 C 0.3261(6) 0.1421(3) 0.5383(2) 0.0271(9) Uani 1 1 d . . . . .
C6 C 0.3479(6) 0.5564(3) 0.7255(3) 0.0310(10) Uani 1 1 d . . . . .
H6A H 0.458008 0.601505 0.707750 0.047 Uiso 1 1 calc GR . . . .
H6B H 0.370583 0.538472 0.787472 0.047 Uiso 1 1 calc GR . . . .
H6C H 0.226381 0.600660 0.714847 0.047 Uiso 1 1 calc GR . . . .
F1 F 0.1611(3) 0.22772(18) 0.64662(14) 0.0348(6) Uani 1 1 d . . . . .
F2 F 0.4753(3) 0.25076(19) 0.64892(15) 0.0347(7) Uani 1 1 d . . . . .
F3 F 0.3105(4) 0.04586(17) 0.58580(14) 0.0363(7) Uani 1 1 d . . . . .
F4 F 0.5047(4) 0.14201(18) 0.50894(15) 0.0354(6) Uani 1 1 d . . . . .
O1 O 0.3312(4) 0.4525(2) 0.67690(16) 0.0284(7) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.025(2) 0.021(2) 0.0232(18) -0.0044(15) 0.0011(17) -0.0022(17)
C2 0.022(2) 0.0246(19) 0.0166(18) -0.0028(16) -0.0006(16) -0.0007(17)
C3 0.023(2) 0.0194(19) 0.0189(18) -0.0006(15) 0.0009(16) -0.0004(17)
C4 0.033(2) 0.023(2) 0.0172(17) -0.0010(17) -0.0025(18) 0.0019(18)
C5 0.040(3) 0.020(2) 0.021(2) 0.0043(17) 0.0018(18) -0.0006(18)
C6 0.045(3) 0.026(2) 0.022(2) -0.0078(18) 0.0026(17) -0.0031(18)
F1 0.0523(18) 0.0288(12) 0.0254(12) 0.0019(10) 0.0142(11) -0.0019(10)
F2 0.0437(17) 0.0294(12) 0.0281(13) 0.0017(11) -0.0121(10) 0.0019(11)
F3 0.0616(18) 0.0190(11) 0.0268(12) 0.0041(10) -0.0042(11) 0.0010(11)
F4 0.0344(14) 0.0345(13) 0.0368(14) -0.0019(12) -0.0003(12) 0.0077(11)
O1 0.0458(18) 0.0224(13) 0.0153(13) -0.0021(12) -0.0053(12) -0.0017(12)
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'
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
C2 C1 C1 120.5(2) . 2_556 ?
C1 C2 C3 119.8(3) . . ?
O1 C2 C1 124.4(3) . . ?
O1 C2 C3 115.8(3) . . ?
C2 C3 C3 119.59(19) . 2_556 ?
C2 C3 C4 118.7(3) . . ?
C3 C3 C4 121.71(19) 2_556 . ?
C3 C4 C5 113.7(3) . . ?
F1 C4 C3 111.4(3) . . ?
F1 C4 C5 108.3(3) . . ?
F1 C4 F2 106.1(3) . . ?
F2 C4 C3 111.8(3) . . ?
F2 C4 C5 105.2(3) . . ?
C5 C5 C4 111.4(3) 2_556 . ?
F3 C5 C4 109.8(3) . . ?
F3 C5 C5 110.2(3) . 2_556 ?
F4 C5 C4 109.2(3) . . ?
F4 C5 C5 108.5(4) . 2_556 ?
F4 C5 F3 107.7(3) . . ?
C2 O1 C6 117.9(3) . . ?
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
C1 C1 1.382(7) 2_556 ?
C1 C2 1.374(5) . ?
C2 C3 1.391(5) . ?
C2 O1 1.359(4) . ?
C3 C3 1.405(7) 2_556 ?
C3 C4 1.499(5) . ?
C4 C5 1.525(5) . ?
C4 F1 1.350(4) . ?
C4 F2 1.360(4) . ?
C5 C5 1.506(7) 2_556 ?
C5 F3 1.352(4) . ?
C5 F4 1.344(4) . ?
C6 O1 1.426(4) . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.673(2)
2 0.327(2)
