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#$Date: 2022-08-10 03:30:03 +0300 (Wed, 10 Aug 2022) $
#$Revision: 277181 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/88/7158815.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_7158815
loop_
_publ_author_name
'Golubev, Alexander S.'
'Ostapchuk, Petr N.'
'Strelkova, Tatyana V.'
'Kagramanov, Nikolai D.'
'Suponitsky, Kyrill'
'Takazova, Rina'
'Chkanikov, Nikolai D.'
_publ_section_title
;
 Synthesis of 4-trifluoromethyl-2H-chromenes via the reaction of
 2-(trifluoroacetyl)phenols with vinyltriphenylphosphonium chloride
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01177H
_journal_year                    2022
_chemical_formula_moiety         'C12 H11 F3 O'
_chemical_formula_sum            'C12 H11 F3 O'
_chemical_formula_weight         228.21
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2022-04-28 deposited with the CCDC.	2022-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.382(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7631(12)
_cell_length_b                   10.2430(14)
_cell_length_c                   10.4343(13)
_cell_measurement_reflns_used    2142
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      22.37
_cell_measurement_theta_min      2.79
_cell_volume                     1042.6(2)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9722
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_min         2.088
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0408
_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)+(0.0664P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1141
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1414
_reflns_number_total             2108
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01177h2.cif
_cod_data_source_block           gol1574
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7158815
_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.
;
_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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.86556(11) 0.05205(11) 0.97243(11) 0.0359(3) Uani 1 1 d . . . . .
F2 F 0.71661(11) 0.02777(11) 1.11656(10) 0.0359(3) Uani 1 1 d . . . . .
F3 F 0.66540(12) 0.13762(11) 0.94558(11) 0.0398(3) Uani 1 1 d . . . . .
O1 O 0.53580(13) -0.31541(12) 0.85306(11) 0.0282(3) Uani 1 1 d . . . . .
C1 C 0.65191(19) -0.32795(18) 0.93193(16) 0.0241(4) Uani 1 1 d . . . . .
C2 C 0.68275(19) -0.45068(18) 0.98020(17) 0.0261(4) Uani 1 1 d . . . . .
H2A H 0.6274 -0.5230 0.9541 0.031 Uiso 1 1 calc R U . . .
C3 C 0.7936(2) -0.46997(18) 1.06637(17) 0.0265(4) Uani 1 1 d . . . . .
C4 C 0.87582(19) -0.36270(19) 1.10326(17) 0.0256(4) Uani 1 1 d . . . . .
C5 C 0.84161(18) -0.24026(19) 1.05580(16) 0.0252(4) Uani 1 1 d . . . . .
H5A H 0.8967 -0.1677 1.0818 0.030 Uiso 1 1 calc R U . . .
C6 C 0.72915(18) -0.21934(18) 0.97106(15) 0.0228(4) Uani 1 1 d . . . . .
C7 C 0.68022(18) -0.09094(18) 0.92436(17) 0.0242(4) Uani 1 1 d . . . . .
C8 C 0.58854(19) -0.08506(19) 0.82627(18) 0.0271(5) Uani 1 1 d . . . . .
H8A H 0.5558 -0.0029 0.7959 0.033 Uiso 1 1 calc R U . . .
C9 C 0.5376(2) -0.20790(19) 0.76458(17) 0.0284(5) Uani 1 1 d . . . . .
H9A H 0.4437 -0.1934 0.7279 0.034 Uiso 1 1 calc R U . . .
H9B H 0.5970 -0.2305 0.6932 0.034 Uiso 1 1 calc R U . . .
C10 C 0.8233(2) -0.60498(19) 1.11786(19) 0.0346(5) Uani 1 1 d . . . . .
H10A H 0.7474 -0.6635 1.0927 0.052 Uiso 1 1 calc R U . . .
H10B H 0.8335 -0.6016 1.2116 0.052 Uiso 1 1 calc R U . . .
H10C H 0.9082 -0.6377 1.0827 0.052 Uiso 1 1 calc R U . . .
C11 C 0.9982(2) -0.3801(2) 1.19498(19) 0.0340(5) Uani 1 1 d . . . . .
H11A H 1.0521 -0.2993 1.1984 0.051 Uiso 1 1 calc R U . . .
H11B H 1.0553 -0.4518 1.1653 0.051 Uiso 1 1 calc R U . . .
H11C H 0.9667 -0.4003 1.2807 0.051 Uiso 1 1 calc R U . . .
C12 C 0.73080(19) 0.03068(19) 0.98918(18) 0.0284(5) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C9 115.03(14) . . ?
O1 C1 C2 117.60(16) . . ?
O1 C1 C6 121.41(16) . . ?
C2 C1 C6 120.76(17) . . ?
C1 C2 C3 121.07(17) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 H2A 119.5 . . ?
C2 C3 C4 119.07(17) . . ?
C2 C3 C10 119.55(17) . . ?
C4 C3 C10 121.38(17) . . ?
C5 C4 C3 118.94(17) . . ?
C5 C4 C11 120.41(17) . . ?
C3 C4 C11 120.64(17) . . ?
C4 C5 C6 122.47(17) . . ?
C4 C5 H5A 118.8 . . ?
C6 C5 H5A 118.8 . . ?
C1 C6 C5 117.63(17) . . ?
C1 C6 C7 116.78(16) . . ?
C5 C6 C7 125.51(17) . . ?
C8 C7 C6 119.46(17) . . ?
C8 C7 C12 120.64(18) . . ?
C6 C7 C12 119.88(16) . . ?
C7 C8 C9 119.69(18) . . ?
C7 C8 H8A 120.2 . . ?
C9 C8 H8A 120.2 . . ?
O1 C9 C8 112.47(15) . . ?
O1 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
O1 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
F3 C12 F2 106.70(15) . . ?
F3 C12 F1 106.06(15) . . ?
F2 C12 F1 105.82(15) . . ?
F3 C12 C7 112.65(16) . . ?
F2 C12 C7 112.62(15) . . ?
F1 C12 C7 112.47(15) . . ?
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 1.352(2) . ?
F2 C12 1.342(2) . ?
F3 C12 1.338(2) . ?
O1 C1 1.379(2) . ?
O1 C9 1.438(2) . ?
C1 C2 1.383(3) . ?
C1 C6 1.395(2) . ?
C2 C3 1.392(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.405(3) . ?
C3 C10 1.507(3) . ?
C4 C5 1.384(3) . ?
C4 C11 1.510(3) . ?
C5 C6 1.397(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.475(3) . ?
C7 C8 1.333(3) . ?
C7 C12 1.492(3) . ?
C8 C9 1.489(3) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
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
C9 O1 C1 C2 -154.71(16) . . . . ?
C9 O1 C1 C6 30.8(2) . . . . ?
O1 C1 C2 C3 -176.21(16) . . . . ?
C6 C1 C2 C3 -1.7(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C1 C2 C3 C10 179.45(16) . . . . ?
C2 C3 C4 C5 2.0(3) . . . . ?
C10 C3 C4 C5 -178.21(16) . . . . ?
C2 C3 C4 C11 -179.07(17) . . . . ?
C10 C3 C4 C11 0.8(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C11 C4 C5 C6 -179.82(16) . . . . ?
O1 C1 C6 C5 177.07(15) . . . . ?
C2 C1 C6 C5 2.8(3) . . . . ?
O1 C1 C6 C7 0.2(2) . . . . ?
C2 C1 C6 C7 -174.08(16) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
C4 C5 C6 C7 175.04(16) . . . . ?
C1 C6 C7 C8 -15.8(2) . . . . ?
C5 C6 C7 C8 167.59(17) . . . . ?
C1 C6 C7 C12 162.58(16) . . . . ?
C5 C6 C7 C12 -14.0(3) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C12 C7 C8 C9 -178.88(16) . . . . ?
C1 O1 C9 C8 -45.0(2) . . . . ?
C7 C8 C9 O1 30.5(2) . . . . ?
C8 C7 C12 F3 5.7(2) . . . . ?
C6 C7 C12 F3 -172.71(15) . . . . ?
C8 C7 C12 F2 126.43(19) . . . . ?
C6 C7 C12 F2 -52.0(2) . . . . ?
C8 C7 C12 F1 -114.11(19) . . . . ?
C6 C7 C12 F1 67.5(2) . . . . ?
