#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/17/7121762.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_7121762
loop_
_publ_author_name
'Yokoo, Kazuma'
'Mori, Keiji'
_publ_section_title
;
 Divergent synthesis of CF₃-substituted polycyclic skeletons
 based on control of activation site of acid catalysts.
;
_journal_issue                   50
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6927
_journal_page_last               6930
_journal_paper_doi               10.1039/c8cc02377h
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C17 H13 F3 O'
_chemical_formula_weight         290.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2018-03-13 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.1710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9659(17)
_cell_length_b                   8.4037(11)
_cell_length_c                   12.8931(17)
_cell_measurement_reflns_used    3580
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      2.97
_cell_volume                     1291.5(3)
_computing_cell_refinement       'APEX2 '
_computing_data_collection       'APEX2 '
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHELL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7320
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.728
_diffrn_reflns_theta_min         1.708
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3072
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0370
_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)+(0.0360P)²+0.5955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0943
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2647
_reflns_number_total             3072
_reflns_threshold_expression     'I > 2σ'
_cod_data_source_file            c8cc02377h2.cif
_cod_data_source_block           shelxla_a_a_a
_cod_depositor_comments          'Adding full bibliography for 7121762.cif.'
_cod_database_code               7121762
_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   0.976
_shelx_estimated_absorpt_t_max   0.976
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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
C1 C 0.37815(10) 0.29766(15) 0.55481(10) 0.0169(2) Uani 1 1 d . .
C2 C 0.42635(11) 0.20097(15) 0.49866(11) 0.0203(3) Uani 1 1 d . .
H2 H 0.3818 0.1242 0.4460 0.024 Uiso 1 1 calc R U
C3 C 0.53960(11) 0.21628(16) 0.51934(12) 0.0242(3) Uani 1 1 d . .
H3 H 0.5722 0.1504 0.4805 0.029 Uiso 1 1 calc R U
C4 C 0.60485(11) 0.32761(17) 0.59663(12) 0.0259(3) Uani 1 1 d . .
H4 H 0.6825 0.3369 0.6118 0.031 Uiso 1 1 calc R U
C5 C 0.55660(11) 0.42537(17) 0.65165(11) 0.0245(3) Uani 1 1 d . .
H5 H 0.6017 0.5016 0.7045 0.029 Uiso 1 1 calc R U
C6 C 0.44271(11) 0.41363(15) 0.63066(10) 0.0201(3) Uani 1 1 d . .
C7 C 0.38946(12) 0.53032(18) 0.68378(12) 0.0270(3) Uani 1 1 d . .
H7A H 0.3771 0.6321 0.6419 0.032 Uiso 1 1 calc R U
H7B H 0.4428 0.5512 0.7621 0.032 Uiso 1 1 calc R U
C8 C 0.27678(12) 0.47564(17) 0.68635(11) 0.0255(3) Uani 1 1 d . .
H8 H 0.2841 0.4798 0.7664 0.031 Uiso 1 1 calc R U
C9 C 0.17728(12) 0.57731(18) 0.61657(12) 0.0276(3) Uani 1 1 d . .
H9A H 0.1111 0.5466 0.6323 0.033 Uiso 1 1 calc R U
H9B H 0.1941 0.6906 0.6374 0.033 Uiso 1 1 calc R U
C10 C 0.15133(10) 0.55581(16) 0.49233(11) 0.0206(3) Uani 1 1 d . .
C11 C 0.09341(11) 0.67322(17) 0.41427(12) 0.0254(3) Uani 1 1 d . .
H11 H 0.0683 0.7660 0.4395 0.030 Uiso 1 1 calc R U
C12 C 0.07197(11) 0.65663(17) 0.30078(12) 0.0253(3) Uani 1 1 d . .
H12 H 0.0313 0.7365 0.2486 0.030 Uiso 1 1 calc R U
C13 C 0.11013(10) 0.52313(17) 0.26371(11) 0.0221(3) Uani 1 1 d . .
H13 H 0.0958 0.5116 0.1859 0.027 Uiso 1 1 calc R U
C14 C 0.16926(10) 0.40608(15) 0.33984(10) 0.0179(2) Uani 1 1 d . .
H14 H 0.1974 0.3164 0.3144 0.021 Uiso 1 1 calc R U
C15 C 0.18767(10) 0.41956(15) 0.45423(10) 0.0163(2) Uani 1 1 d . .
C16 C 0.25524(10) 0.29245(15) 0.53909(10) 0.0168(2) Uani 1 1 d . .
C17 C 0.20052(10) 0.12771(16) 0.50687(10) 0.0199(3) Uani 1 1 d . .
F1 F 0.25727(7) 0.01681(10) 0.58277(7) 0.0285(2) Uani 1 1 d . .
F2 F 0.19352(6) 0.07486(9) 0.40624(6) 0.02370(18) Uani 1 1 d . .
F3 F 0.09527(6) 0.12846(10) 0.50222(7) 0.02696(19) Uani 1 1 d . .
O1 O 0.25062(8) 0.31401(11) 0.64739(7) 0.0228(2) Uani 1 1 d . .
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
C2 C1 C6 120.18(11)
C2 C1 C16 125.05(11)
C6 C1 C16 114.75(11)
C1 C2 C3 120.21(12)
C1 C2 H2 119.9
C3 C2 H2 119.9
C4 C3 C2 120.00(13)
C4 C3 H3 120.0
C2 C3 H3 120.0
C5 C4 C3 119.84(12)
C5 C4 H4 120.1
C3 C4 H4 120.1
C4 C5 C6 121.01(12)
C4 C5 H5 119.5
C6 C5 H5 119.5
C5 C6 C1 118.71(12)
C5 C6 C7 120.25(12)
C1 C6 C7 120.94(12)
C6 C7 C8 114.95(11)
C6 C7 H7A 108.5
C8 C7 H7A 108.5
C6 C7 H7B 108.5
C8 C7 H7B 108.5
H7A C7 H7B 107.5
O1 C8 C9 107.23(11)
O1 C8 C7 111.58(11)
C9 C8 C7 114.31(12)
O1 C8 H8 107.8
C9 C8 H8 107.8
C7 C8 H8 107.8
C10 C9 C8 110.15(11)
C10 C9 H9A 109.6
C8 C9 H9A 109.6
C10 C9 H9B 109.6
C8 C9 H9B 109.6
H9A C9 H9B 108.1
C11 C10 C15 118.98(12)
C11 C10 C9 120.70(12)
C15 C10 C9 120.29(12)
C12 C11 C10 121.14(13)
C12 C11 H11 119.4
C10 C11 H11 119.4
C13 C12 C11 119.72(12)
C13 C12 H12 120.1
C11 C12 H12 120.1
C12 C13 C14 120.20(12)
C12 C13 H13 119.9
C14 C13 H13 119.9
C13 C14 C15 120.29(12)
C13 C14 H14 119.9
C15 C14 H14 119.9
C10 C15 C14 119.60(11)
C10 C15 C16 119.76(11)
C14 C15 C16 120.46(11)
O1 C16 C1 108.00(9)
O1 C16 C15 112.09(10)
C1 C16 C15 110.39(10)
O1 C16 C17 100.70(9)
C1 C16 C17 114.13(10)
C15 C16 C17 111.18(10)
F2 C17 F1 106.54(11)
F2 C17 F3 106.14(10)
F1 C17 F3 106.97(10)
F2 C17 C16 114.11(10)
F1 C17 C16 111.48(10)
F3 C17 C16 111.17(10)
C16 O1 C8 111.38(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3896(18)
C1 C6 1.4010(17)
C1 C16 1.5259(16)
C2 C3 1.3912(18)
C2 H2 0.9500
C3 C4 1.386(2)
C3 H3 0.9500
C4 C5 1.385(2)
C4 H4 0.9500
C5 C6 1.3960(19)
C5 H5 0.9500
C6 C7 1.5098(19)
C7 C8 1.544(2)
C7 H7A 0.9900
C7 H7B 0.9900
C8 O1 1.4416(17)
C8 C9 1.513(2)
C8 H8 1.0000
C9 C10 1.5125(18)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.3984(19)
C10 C15 1.3988(17)
C11 C12 1.385(2)
C11 H11 0.9500
C12 C13 1.385(2)
C12 H12 0.9500
C13 C14 1.3881(18)
C13 H13 0.9500
C14 C15 1.4028(16)
C14 H14 0.9500
C15 C16 1.5335(17)
C16 O1 1.4324(14)
C16 C17 1.5364(17)
C17 F2 1.3402(15)
C17 F1 1.3421(15)
C17 F3 1.3423(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139188738
