#------------------------------------------------------------------------------
#$Date: 2022-09-06 12:56:21 +0300 (Tue, 06 Sep 2022) $
#$Revision: 277657 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/74/1567477.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_1567477
loop_
_publ_author_name
'Delamare, Aline'
'Naulet, Guillaume'
'Kauffmann, Brice'
'Guichard, Gilles'
'Compain, Guillaume'
_publ_section_title
;
 Hexafluoroisobutylation of enolates through a tandem elimination/allylic
 shift/hydrofluorination reaction
;
_journal_issue                   33
_journal_name_full               'Chemical Science'
_journal_page_first              9507
_journal_page_last               9514
_journal_paper_doi               10.1039/D2SC02871A
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C8 H8 F6 O2'
_chemical_formula_sum            'C8 H8 F6 O2'
_chemical_formula_weight         250.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-01-26 deposited with the CCDC.	2022-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.361(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2917(4)
_cell_length_b                   16.6360(10)
_cell_length_c                   9.1660(7)
_cell_measurement_reflns_used    1512
_cell_measurement_temperature    145
_cell_measurement_theta_max      72.2770
_cell_measurement_theta_min      5.3360
_cell_volume                     937.15(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_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    'SHELXD  (Sheldrick, 2008)'
_diffrn_ambient_temperature      145
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -126.00 -15.00   1.00    1.00    --  -36.30  55.00-120.00  111
  2  ω   -104.00 -28.00   1.00    1.00    --  -36.30  28.00-150.00   76
  3  ω   -126.00 -86.00   1.00    1.00    --  -36.30  55.00-180.00   40
  4  ω     26.00  51.00   1.00    1.00    --  -36.30  55.00-120.00   25
  5  ω    -42.00  52.00   1.00    1.00    --  -36.30  55.00-180.00   94
  6  ω   -159.00-132.00   1.00    2.00    -- -110.00   9.00-180.00   27
  7  ω    -57.00 -21.00   1.00    2.00    -- -110.00  55.00-156.20   36
  8  ω   -178.00-140.00   1.00    2.00    -- -110.00  55.00-156.20   38
  9  ω    -90.00 -61.00   1.00    2.00    -- -110.00  55.00-156.20   29
 10  ω    -74.00 -48.00   1.00    2.00    -- -110.00   9.00-120.00   26
 11  ω   -198.00 -22.00   1.00    2.00    -- -110.00  55.00-105.99  176
 12  ω   -158.00 -78.00   1.00    2.00    -- -110.00   9.00-120.00   80
 13  ω   -133.00 -96.00   1.00    2.00    -- -110.00  55.00-156.20   37
 14  ω    -93.00 -22.00   1.00    2.00    -- -110.00  54.00 -54.60   71
 15  ω   -111.00 -65.00   1.00    2.00    -- -110.00   9.00-180.00   46
 16  ω   -161.00-114.00   1.00    2.00    -- -110.00  54.00 -54.60   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku FRX'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0621070000
_diffrn_orient_matrix_UB_12      0.0884831000
_diffrn_orient_matrix_UB_13      -0.0370412000
_diffrn_orient_matrix_UB_21      -0.2420413000
_diffrn_orient_matrix_UB_22      -0.0236507000
_diffrn_orient_matrix_UB_23      -0.0402080000
_diffrn_orient_matrix_UB_31      -0.0174820000
_diffrn_orient_matrix_UB_32      0.0141751000
_diffrn_orient_matrix_UB_33      0.1631022000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1849
_diffrn_reflns_point_group_measured_fraction_full 0.624
_diffrn_reflns_point_group_measured_fraction_max 0.609
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.400
_diffrn_reflns_theta_min         5.318
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.844
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1125
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0552
_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)+(0.1369P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.1527
_reflns_Friedel_coverage         0.247
_reflns_Friedel_fraction_full    0.259
_reflns_Friedel_fraction_max     0.243
_reflns_number_gt                1113
_reflns_number_total             1125
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc02871a2.cif
_cod_data_source_block           gc_x1
_cod_depositor_comments
'Adding full bibliography for 1567476--1567479.cif.'
_cod_original_cell_volume        937.15(12)
_cod_database_code               1567477
_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.
;
_reflns_odcompleteness_completeness 98.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C014(H014), C015(H015)
2.b Secondary CH2 refined with riding coordinates:
 C006(H00A,H00B), C011(H01A,H01B), C016(H01C,H01D)
;
_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 5.283
_oxdiff_exptl_absorpt_empirical_full_min 0.396
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'
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
O001 O 0.9300(4) 0.97059(16) 0.3170(3) 0.0215(6) Uani 1 1 d . . . . .
F002 F 0.9181(5) 1.17267(14) 0.6938(3) 0.0283(6) Uani 1 1 d . . . . .
F003 F 1.4490(5) 1.1728(2) 0.6060(4) 0.0417(8) Uani 1 1 d . . . . .
F004 F 1.3074(4) 1.20624(15) 0.3808(3) 0.0307(6) Uani 1 1 d . . . . .
O005 O 0.7594(4) 0.99778(14) 0.0829(3) 0.0209(7) Uani 1 1 d . . . . .
C006 C 0.8868(5) 1.14453(19) 0.3809(4) 0.0171(8) Uani 1 1 d . . . . .
H00A H 0.760339 1.122410 0.411281 0.020 Uiso 1 1 calc R U . . .
H00B H 0.868204 1.202355 0.372755 0.020 Uiso 1 1 calc R U . . .
F007 F 0.9013(5) 1.04612(16) 0.6433(3) 0.0372(7) Uani 1 1 d . . . . .
F008 F 1.1941(5) 1.26174(15) 0.5616(4) 0.0349(7) Uani 1 1 d . . . . .
F009 F 1.2012(5) 1.09807(19) 0.7634(3) 0.0376(7) Uani 1 1 d . . . . .
C010 C 1.2616(7) 1.1914(2) 0.5143(5) 0.0226(8) Uani 1 1 d . . . . .
C011 C 0.7073(7) 1.0691(2) -0.0104(5) 0.0238(8) Uani 1 1 d . . . . .
H01A H 0.563636 1.064479 -0.074480 0.029 Uiso 1 1 calc R U . . .
H01B H 0.812941 1.076788 -0.072243 0.029 Uiso 1 1 calc R U . . .
C012 C 1.0300(6) 1.1112(2) 0.6523(5) 0.0219(8) Uani 1 1 d . . . . .
C013 C 0.8694(6) 1.0202(2) 0.2207(4) 0.0176(7) Uani 1 1 d . . . . .
C014 C 0.8984(6) 1.11083(18) 0.2297(4) 0.0161(7) Uani 1 1 d . . . . .
H014 H 1.039508 1.124718 0.207550 0.019 Uiso 1 1 calc R U . . .
C015 C 1.0930(6) 1.1256(2) 0.5032(4) 0.0177(7) Uani 1 1 d . . . . .
H015 H 1.157096 1.075804 0.474794 0.021 Uiso 1 1 calc R U . . .
C016 C 0.7154(7) 1.1383(2) 0.0986(5) 0.0217(8) Uani 1 1 d . . . . .
H01C H 0.578138 1.144454 0.129546 0.026 Uiso 1 1 calc R U . . .
H01D H 0.752049 1.188511 0.056076 0.026 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 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C013 O005 C011 109.1(3) . . ?
H00A C006 H00B 107.8 . . ?
C014 C006 H00A 109.0 . . ?
C014 C006 H00B 109.0 . . ?
C014 C006 C015 112.9(3) . . ?
C015 C006 H00A 109.0 . . ?
C015 C006 H00B 109.0 . . ?
F003 C010 F004 106.6(3) . . ?
F003 C010 F008 107.2(4) . . ?
F003 C010 C015 112.8(3) . . ?
F004 C010 F008 106.2(3) . . ?
F004 C010 C015 110.9(3) . . ?
F008 C010 C015 112.7(3) . . ?
O005 C011 H01A 110.7 . . ?
O005 C011 H01B 110.7 . . ?
O005 C011 C016 105.1(3) . . ?
H01A C011 H01B 108.8 . . ?
C016 C011 H01A 110.7 . . ?
C016 C011 H01B 110.7 . . ?
F002 C012 F007 106.6(3) . . ?
F002 C012 C015 112.8(3) . . ?
F007 C012 C015 110.0(3) . . ?
F009 C012 F002 107.2(3) . . ?
F009 C012 F007 107.0(3) . . ?
F009 C012 C015 112.9(3) . . ?
O001 C013 O005 120.7(3) . . ?
O001 C013 C014 128.5(3) . . ?
O005 C013 C014 110.8(3) . . ?
C006 C014 C013 112.9(3) . . ?
C006 C014 H014 109.1 . . ?
C006 C014 C016 115.4(3) . . ?
C013 C014 H014 109.1 . . ?
C013 C014 C016 101.0(3) . . ?
C016 C014 H014 109.1 . . ?
C006 C015 H015 107.9 . . ?
C010 C015 C006 111.5(3) . . ?
C010 C015 C012 111.6(3) . . ?
C010 C015 H015 107.9 . . ?
C012 C015 C006 110.0(3) . . ?
C012 C015 H015 107.9 . . ?
C011 C016 C014 101.6(3) . . ?
C011 C016 H01C 111.4 . . ?
C011 C016 H01D 111.4 . . ?
C014 C016 H01C 111.4 . . ?
C014 C016 H01D 111.4 . . ?
H01C C016 H01D 109.3 . . ?
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
O001 C013 1.209(5) . ?
F002 C012 1.343(4) . ?
F003 C010 1.330(5) . ?
F004 C010 1.339(5) . ?
O005 C011 1.458(5) . ?
O005 C013 1.357(4) . ?
C006 H00A 0.9700 . ?
C006 H00B 0.9700 . ?
C006 C014 1.511(5) . ?
C006 C015 1.555(4) . ?
F007 C012 1.343(4) . ?
F008 C010 1.348(5) . ?
F009 C012 1.333(5) . ?
C010 C015 1.513(5) . ?
C011 H01A 0.9700 . ?
C011 H01B 0.9700 . ?
C011 C016 1.518(5) . ?
C012 C015 1.521(5) . ?
C013 C014 1.518(4) . ?
C014 H014 0.9800 . ?
C014 C016 1.545(5) . ?
C015 H015 0.9800 . ?
C016 H01C 0.9700 . ?
C016 H01D 0.9700 . ?
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
O001 C013 C014 C006 -35.2(5) . . . . ?
O001 C013 C014 C016 -159.0(4) . . . . ?
F002 C012 C015 C006 -55.5(4) . . . . ?
F002 C012 C015 C010 68.7(4) . . . . ?
F003 C010 C015 C006 -173.0(3) . . . . ?
F003 C010 C015 C012 63.6(4) . . . . ?
F004 C010 C015 C006 -53.5(4) . . . . ?
F004 C010 C015 C012 -176.9(3) . . . . ?
O005 C011 C016 C014 33.8(4) . . . . ?
O005 C013 C014 C006 144.7(3) . . . . ?
O005 C013 C014 C016 20.9(4) . . . . ?
C006 C014 C016 C011 -154.3(3) . . . . ?
F007 C012 C015 C006 63.3(4) . . . . ?
F007 C012 C015 C010 -172.4(3) . . . . ?
F008 C010 C015 C006 65.4(4) . . . . ?
F008 C010 C015 C012 -58.0(4) . . . . ?
F009 C012 C015 C006 -177.2(3) . . . . ?
F009 C012 C015 C010 -52.9(4) . . . . ?
C011 O005 C013 O001 -179.8(3) . . . . ?
C011 O005 C013 C014 0.3(4) . . . . ?
C013 O005 C011 C016 -22.1(4) . . . . ?
C013 C014 C016 C011 -32.2(4) . . . . ?
C014 C006 C015 C010 91.1(3) . . . . ?
C014 C006 C015 C012 -144.6(3) . . . . ?
C015 C006 C014 C013 73.4(4) . . . . ?
C015 C006 C014 C016 -171.1(3) . . . . ?
