#------------------------------------------------------------------------------
#$Date: 2020-07-06 06:42:57 +0300 (Mon, 06 Jul 2020) $
#$Revision: 253969 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157529.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_7157529
loop_
_publ_author_name
'Terashima, Kyu'
'Kawasaki-Takasuka, Tomoko'
'Agou, Tomohiro'
'Kubota, Toshio'
'Yamazaki, Takashi'
_publ_section_title
;
 Syntheses of α-CF₃-α-quaternary ketones via p-quinone
 methides and their derivatization to compounds with successively
 congested stereogenic centers.
;
_journal_issue                   24
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4638
_journal_page_last               4644
_journal_paper_doi               10.1039/d0ob00951b
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C17 H17 F3 O2'
_chemical_formula_sum            'C17 H17 F3 O2'
_chemical_formula_weight         310.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-03-27 deposited with the CCDC.	2020-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.3360(11)
_cell_length_b                   7.1684(3)
_cell_length_c                   16.7513(8)
_cell_measurement_reflns_used    8196
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.9280
_cell_measurement_theta_min      2.5560
_cell_volume                     2922.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear-SM Expert ver 2.1'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto, et al., 2019)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto, et al., 2019)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Pilatus P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.432
_diffrn_source                   'Rigaku VariMax'
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2724
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0369
_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)+(0.0422P)²+0.9146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0989
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2283
_reflns_number_total             2724
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00951b2.cif
_cod_data_source_block           Kyu3
_cod_depositor_comments
'Adding full bibliography for 7157528--7157531.cif.'
_cod_database_code               7157529
_shelx_shelxl_version_number     2014/7
_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   0.975
_shelx_estimated_absorpt_t_max   0.985
_oxdiff_exptl_absorpt_empirical_full_min 0.338
_oxdiff_exptl_absorpt_empirical_full_max 2.154
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, 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 0.31384(4) 0.50028(13) 0.71333(5) 0.0388(3) Uani 1 1 d . . . . .
F2 F 0.28895(4) 0.30578(14) 0.62355(6) 0.0395(3) Uani 1 1 d . . . . .
F3 F 0.33099(4) 0.55807(13) 0.59066(6) 0.0438(3) Uani 1 1 d . . . . .
O1 O 0.48005(4) 0.12699(16) 0.34973(6) 0.0324(3) Uani 1 1 d . . . . .
H1 H 0.4567 0.0771 0.3195 0.049 Uiso 1 1 calc R U . . .
O2 O 0.43849(4) 0.08909(16) 0.72616(6) 0.0319(3) Uani 1 1 d . . . . .
H2 H 0.4546 0.0447 0.6861 0.048 Uiso 1 1 calc R U . . .
C1 C 0.40948(6) 0.27934(19) 0.56829(8) 0.0222(3) Uani 1 1 d . . . . .
C2 C 0.35419(6) 0.1704(2) 0.78468(8) 0.0230(3) Uani 1 1 d . . . . .
C3 C 0.45519(6) 0.1788(2) 0.41990(9) 0.0248(3) Uani 1 1 d . . . . .
C4 C 0.38674(6) 0.3258(2) 0.65199(8) 0.0231(3) Uani 1 1 d . . . . .
C5 C 0.38307(6) 0.1389(2) 0.70487(8) 0.0233(3) Uani 1 1 d . . . . .
C6 C 0.39885(6) 0.1835(2) 0.43003(9) 0.0284(4) Uani 1 1 d . . . . .
H3 H 0.3753 0.1538 0.3866 0.034 Uiso 1 1 calc R U . . .
C7 C 0.37669(6) 0.2314(2) 0.50348(9) 0.0279(3) Uani 1 1 d . . . . .
H4 H 0.3379 0.2314 0.5097 0.034 Uiso 1 1 calc R U . . .
C8 C 0.38198(6) 0.2533(2) 0.84825(9) 0.0277(3) Uani 1 1 d . . . . .
H5 H 0.4190 0.2922 0.8414 0.033 Uiso 1 1 calc R U . . .
C9 C 0.30026(6) 0.1139(2) 0.79722(10) 0.0300(4) Uani 1 1 d . . . . .
H6 H 0.2805 0.0568 0.7549 0.036 Uiso 1 1 calc R U . . .
C10 C 0.46609(6) 0.2788(2) 0.55547(9) 0.0290(4) Uani 1 1 d . . . . .
H7 H 0.4898 0.3140 0.5979 0.035 Uiso 1 1 calc R U . . .
C11 C 0.48872(6) 0.2285(2) 0.48288(9) 0.0309(4) Uani 1 1 d . . . . .
H8 H 0.5275 0.2281 0.4763 0.037 Uiso 1 1 calc R U . . .
C12 C 0.33038(7) 0.4194(2) 0.64496(9) 0.0303(4) Uani 1 1 d . . . . .
C13 C 0.35657(7) 0.2799(2) 0.92102(10) 0.0334(4) Uani 1 1 d . . . . .
H9 H 0.3761 0.3378 0.9634 0.040 Uiso 1 1 calc R U . . .
C14 C 0.30277(7) 0.2226(2) 0.93253(10) 0.0354(4) Uani 1 1 d . . . . .
H10 H 0.2853 0.2403 0.9827 0.043 Uiso 1 1 calc R U . . .
C15 C 0.42370(7) 0.4726(2) 0.69279(9) 0.0335(4) Uani 1 1 d . . . . .
H11 H 0.4291 0.5786 0.6567 0.050 Uiso 1 1 calc R U . . .
H12 H 0.4594 0.4167 0.7055 0.050 Uiso 1 1 calc R U . . .
H13 H 0.4061 0.5158 0.7420 0.050 Uiso 1 1 calc R U . . .
C16 C 0.35882(7) -0.0257(2) 0.65912(10) 0.0338(4) Uani 1 1 d . . . . .
H14 H 0.3825 -0.0557 0.6136 0.051 Uiso 1 1 calc R U . . .
H15 H 0.3220 0.0070 0.6399 0.051 Uiso 1 1 calc R U . . .
H16 H 0.3564 -0.1342 0.6945 0.051 Uiso 1 1 calc R U . . .
C17 C 0.27485(7) 0.1395(2) 0.87036(10) 0.0354(4) Uani 1 1 d . . . . .
H17 H 0.2380 0.0996 0.8778 0.042 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'
O O 0.0106 0.0060 '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
C3 O1 H1 109.5 . . ?
C5 O2 H2 109.5 . . ?
C7 C1 C10 116.50(13) . . ?
C7 C1 C4 123.82(12) . . ?
C10 C1 C4 119.65(13) . . ?
C9 C2 C8 117.83(14) . . ?
C9 C2 C5 121.60(13) . . ?
C8 C2 C5 120.55(13) . . ?
O1 C3 C11 117.61(13) . . ?
O1 C3 C6 123.27(13) . . ?
C11 C3 C6 119.11(13) . . ?
C12 C4 C15 104.89(12) . . ?
C12 C4 C1 110.23(12) . . ?
C15 C4 C1 109.89(12) . . ?
C12 C4 C5 110.96(12) . . ?
C15 C4 C5 110.88(12) . . ?
C1 C4 C5 109.89(11) . . ?
O2 C5 C16 107.15(12) . . ?
O2 C5 C2 104.53(11) . . ?
C16 C5 C2 112.08(12) . . ?
O2 C5 C4 106.91(11) . . ?
C16 C5 C4 112.90(12) . . ?
C2 C5 C4 112.61(11) . . ?
C3 C6 C7 120.04(14) . . ?
C3 C6 H3 120.0 . . ?
C7 C6 H3 120.0 . . ?
C6 C7 C1 122.06(13) . . ?
C6 C7 H4 119.0 . . ?
C1 C7 H4 119.0 . . ?
C13 C8 C2 121.07(14) . . ?
C13 C8 H5 119.5 . . ?
C2 C8 H5 119.5 . . ?
C17 C9 C2 121.13(15) . . ?
C17 C9 H6 119.4 . . ?
C2 C9 H6 119.4 . . ?
C11 C10 C1 121.99(14) . . ?
C11 C10 H7 119.0 . . ?
C1 C10 H7 119.0 . . ?
C3 C11 C10 120.25(14) . . ?
C3 C11 H8 119.9 . . ?
C10 C11 H8 119.9 . . ?
F2 C12 F1 105.29(12) . . ?
F2 C12 F3 105.97(13) . . ?
F1 C12 F3 105.09(12) . . ?
F2 C12 C4 115.24(13) . . ?
F1 C12 C4 113.04(13) . . ?
F3 C12 C4 111.42(12) . . ?
C8 C13 C14 120.36(15) . . ?
C8 C13 H9 119.8 . . ?
C14 C13 H9 119.8 . . ?
C17 C14 C13 119.25(15) . . ?
C17 C14 H10 120.4 . . ?
C13 C14 H10 120.4 . . ?
C4 C15 H11 109.5 . . ?
C4 C15 H12 109.5 . . ?
H11 C15 H12 109.5 . . ?
C4 C15 H13 109.5 . . ?
H11 C15 H13 109.5 . . ?
H12 C15 H13 109.5 . . ?
C5 C16 H14 109.5 . . ?
C5 C16 H15 109.5 . . ?
H14 C16 H15 109.5 . . ?
C5 C16 H16 109.5 . . ?
H14 C16 H16 109.5 . . ?
H15 C16 H16 109.5 . . ?
C14 C17 C9 120.37(15) . . ?
C14 C17 H17 119.8 . . ?
C9 C17 H17 119.8 . . ?
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 C12 1.3452(17) . ?
F2 C12 1.3450(19) . ?
F3 C12 1.3473(18) . ?
O1 C3 1.3732(17) . ?
O1 H1 0.8400 . ?
O2 C5 1.4401(17) . ?
O2 H2 0.8400 . ?
C1 C7 1.391(2) . ?
C1 C10 1.394(2) . ?
C1 C4 1.5437(19) . ?
C2 C9 1.389(2) . ?
C2 C8 1.395(2) . ?
C2 C5 1.5272(19) . ?
C3 C11 1.380(2) . ?
C3 C6 1.382(2) . ?
C4 C12 1.531(2) . ?
C4 C15 1.544(2) . ?
C4 C5 1.6088(19) . ?
C5 C16 1.526(2) . ?
C6 C7 1.387(2) . ?
C6 H3 0.9500 . ?
C7 H4 0.9500 . ?
C8 C13 1.380(2) . ?
C8 H5 0.9500 . ?
C9 C17 1.385(2) . ?
C9 H6 0.9500 . ?
C10 C11 1.383(2) . ?
C10 H7 0.9500 . ?
C11 H8 0.9500 . ?
C13 C14 1.386(2) . ?
C13 H9 0.9500 . ?
C14 C17 1.379(2) . ?
C14 H10 0.9500 . ?
C15 H11 0.9800 . ?
C15 H12 0.9800 . ?
C15 H13 0.9800 . ?
C16 H14 0.9800 . ?
C16 H15 0.9800 . ?
C16 H16 0.9800 . ?
C17 H17 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.84 2.02 2.7761(15) 150.2 8
O2 H2 O1 0.84 2.10 2.8186(14) 143.6 5_656
C16 H15 F2 0.98 2.30 2.9821(19) 125.5 .
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
C7 C1 C4 C12 -32.40(19) . . . . ?
C10 C1 C4 C12 149.59(14) . . . . ?
C7 C1 C4 C15 -147.53(14) . . . . ?
C10 C1 C4 C15 34.46(18) . . . . ?
C7 C1 C4 C5 90.20(16) . . . . ?
C10 C1 C4 C5 -87.82(16) . . . . ?
C9 C2 C5 O2 -141.33(14) . . . . ?
C8 C2 C5 O2 37.08(17) . . . . ?
C9 C2 C5 C16 -25.61(19) . . . . ?
C8 C2 C5 C16 152.79(14) . . . . ?
C9 C2 C5 C4 102.99(16) . . . . ?
C8 C2 C5 C4 -78.61(16) . . . . ?
C12 C4 C5 O2 -164.85(11) . . . . ?
C15 C4 C5 O2 -48.71(15) . . . . ?
C1 C4 C5 O2 72.98(13) . . . . ?
C12 C4 C5 C16 77.57(15) . . . . ?
C15 C4 C5 C16 -166.29(13) . . . . ?
C1 C4 C5 C16 -44.60(16) . . . . ?
C12 C4 C5 C2 -50.61(16) . . . . ?
C15 C4 C5 C2 65.54(15) . . . . ?
C1 C4 C5 C2 -172.78(11) . . . . ?
O1 C3 C6 C7 177.87(14) . . . . ?
C11 C3 C6 C7 -2.2(2) . . . . ?
C3 C6 C7 C1 1.3(2) . . . . ?
C10 C1 C7 C6 0.6(2) . . . . ?
C4 C1 C7 C6 -177.42(14) . . . . ?
C9 C2 C8 C13 -0.5(2) . . . . ?
C5 C2 C8 C13 -179.00(14) . . . . ?
C8 C2 C9 C17 0.1(2) . . . . ?
C5 C2 C9 C17 178.57(14) . . . . ?
C7 C1 C10 C11 -1.7(2) . . . . ?
C4 C1 C10 C11 176.49(14) . . . . ?
O1 C3 C11 C10 -178.86(14) . . . . ?
C6 C3 C11 C10 1.2(2) . . . . ?
C1 C10 C11 C3 0.8(2) . . . . ?
C15 C4 C12 F2 -169.00(12) . . . . ?
C1 C4 C12 F2 72.76(15) . . . . ?
C5 C4 C12 F2 -49.21(16) . . . . ?
C15 C4 C12 F1 -47.85(16) . . . . ?
C1 C4 C12 F1 -166.10(12) . . . . ?
C5 C4 C12 F1 71.93(16) . . . . ?
C15 C4 C12 F3 70.23(15) . . . . ?
C1 C4 C12 F3 -48.02(17) . . . . ?
C5 C4 C12 F3 -169.99(12) . . . . ?
C2 C8 C13 C14 0.6(2) . . . . ?
C8 C13 C14 C17 -0.3(2) . . . . ?
C13 C14 C17 C9 -0.1(2) . . . . ?
C2 C9 C17 C14 0.2(2) . . . . ?
