#------------------------------------------------------------------------------
#$Date: 2020-10-21 07:09:28 +0300 (Wed, 21 Oct 2020) $
#$Revision: 258509 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/14/7241433.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_7241433
loop_
_publ_author_name
'Jha, Babli K.'
'Prudhviraj, Jaggaraju'
'Mainkar, Prathama S.'
'Punna, Nagender'
'Chandrasekhar, Srivari'
_publ_section_title
;
 Diastereoselective synthesis of CF3-dihydrobenzofurans by [4+1]
 annulation of in situ-generated CF3-o-quinone methides and sulfur ylides
;
_journal_issue                   63
_journal_name_full               'RSC Advances'
_journal_page_first              38588
_journal_page_last               38591
_journal_paper_doi               10.1039/D0RA08289A
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C16 H11 F3 O2'
_chemical_formula_sum            'C16 H11 F3 O2'
_chemical_formula_weight         292.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-08-14 deposited with the CCDC.	2020-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                116.090(17)
_cell_angle_beta                 91.310(17)
_cell_angle_gamma                108.693(16)
_cell_formula_units_Z            2
_cell_length_a                   8.056(7)
_cell_length_b                   9.746(9)
_cell_length_c                   10.356(10)
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      30.66
_cell_measurement_theta_min      2.52
_cell_volume                     678.8(11)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16052
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.564
_diffrn_reflns_theta_min         2.232
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0538
_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)+(0.0612P)²+0.2321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1524
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3100
_reflns_number_total             4109
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra08289a2.cif
_cod_data_source_block           KA983_0m
_cod_database_code               7241433
_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.
;
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.979
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.40248(19) 0.69074(16) 0.79592(14) 0.0361(3) Uani 1 1 d . . . . .
H1 H 0.472894 0.771885 0.894151 0.043 Uiso 1 1 calc R U . . .
C2 C 0.16450(19) 0.70502(16) 0.68429(15) 0.0367(3) Uani 1 1 d . . . . .
C3 C -0.0077(2) 0.69179(19) 0.64594(17) 0.0454(3) Uani 1 1 d . . . . .
H3 H -0.098105 0.660385 0.692906 0.054 Uiso 1 1 calc R U . . .
C4 C -0.0393(2) 0.7277(2) 0.53385(19) 0.0533(4) Uani 1 1 d . . . . .
H4 H -0.152926 0.722110 0.506336 0.064 Uiso 1 1 calc R U . . .
C5 C 0.0955(3) 0.7716(3) 0.4621(2) 0.0604(5) Uani 1 1 d . . . . .
H5 H 0.070795 0.794508 0.387145 0.073 Uiso 1 1 calc R U . . .
C6 C 0.2664(2) 0.7816(2) 0.50130(18) 0.0528(4) Uani 1 1 d . . . . .
H6 H 0.356088 0.809167 0.452245 0.063 Uiso 1 1 calc R U . . .
C7 C 0.30100(19) 0.74976(16) 0.61537(14) 0.0376(3) Uani 1 1 d . . . . .
C8 C 0.46927(19) 0.75325(17) 0.68560(15) 0.0384(3) Uani 1 1 d . . . . .
H8 H 0.513848 0.675943 0.611781 0.046 Uiso 1 1 calc R U . . .
C9 C 0.6125(2) 0.9214(2) 0.7594(2) 0.0499(4) Uani 1 1 d . . . . .
C10 C 0.41507(19) 0.52297(16) 0.75788(14) 0.0369(3) Uani 1 1 d . . . . .
C11 C 0.32121(18) 0.43309(16) 0.83601(15) 0.0368(3) Uani 1 1 d . . . . .
C12 C 0.2988(3) 0.2667(2) 0.77973(19) 0.0517(4) Uani 1 1 d . . . . .
H12 H 0.343654 0.216131 0.696954 0.062 Uiso 1 1 calc R U . . .
C13 C 0.2099(3) 0.1784(2) 0.8479(2) 0.0641(5) Uani 1 1 d . . . . .
H13 H 0.193590 0.067988 0.809683 0.077 Uiso 1 1 calc R U . . .
C14 C 0.1449(3) 0.2528(2) 0.9723(2) 0.0613(5) Uani 1 1 d . . . . .
H14 H 0.084860 0.192285 1.017028 0.074 Uiso 1 1 calc R U . . .
C15 C 0.1691(3) 0.4172(2) 1.0302(2) 0.0565(4) Uani 1 1 d . . . . .
H15 H 0.127051 0.467638 1.114797 0.068 Uiso 1 1 calc R U . . .
C16 C 0.2566(2) 0.50725(19) 0.96172(16) 0.0449(3) Uani 1 1 d . . . . .
H16 H 0.271741 0.617494 1.000314 0.054 Uiso 1 1 calc R U . . .
O1 O 0.21744(15) 0.67617(14) 0.79476(12) 0.0453(3) Uani 1 1 d . . . . .
O2 O 0.50049(19) 0.46853(16) 0.66619(14) 0.0584(3) Uani 1 1 d . . . . .
F1 F 0.55669(18) 1.03517(13) 0.85614(14) 0.0742(4) Uani 1 1 d . . . . .
F2 F 0.67258(18) 0.97379(16) 0.66374(16) 0.0808(4) Uani 1 1 d . . . . .
F3 F 0.75433(15) 0.92517(17) 0.83294(16) 0.0812(4) 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
O1 C1 C10 109.24(11) . . ?
O1 C1 C8 107.26(11) . . ?
C10 C1 C8 113.12(11) . . ?
O1 C1 H1 109.1 . . ?
C10 C1 H1 109.1 . . ?
C8 C1 H1 109.1 . . ?
O1 C2 C7 113.46(14) . . ?
O1 C2 C3 123.74(13) . . ?
C7 C2 C3 122.80(14) . . ?
C2 C3 C4 116.88(14) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
C5 C4 C3 121.37(17) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C6 C5 C4 120.55(16) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 118.73(15) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C2 C7 C6 119.64(15) . . ?
C2 C7 C8 108.47(13) . . ?
C6 C7 C8 131.89(13) . . ?
C9 C8 C7 112.73(13) . . ?
C9 C8 C1 112.22(14) . . ?
C7 C8 C1 102.44(12) . . ?
C9 C8 H8 109.7 . . ?
C7 C8 H8 109.7 . . ?
C1 C8 H8 109.7 . . ?
F2 C9 F3 106.65(15) . . ?
F2 C9 F1 106.37(16) . . ?
F3 C9 F1 106.71(16) . . ?
F2 C9 C8 112.16(15) . . ?
F3 C9 C8 111.81(15) . . ?
F1 C9 C8 112.72(15) . . ?
O2 C10 C11 122.21(14) . . ?
O2 C10 C1 119.48(13) . . ?
C11 C10 C1 118.31(12) . . ?
C16 C11 C12 119.17(14) . . ?
C16 C11 C10 122.71(14) . . ?
C12 C11 C10 118.12(14) . . ?
C13 C12 C11 119.80(17) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 120.63(17) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.09(16) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 119.93(18) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 120.35(16) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C2 O1 C1 107.90(10) . . ?
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 O1 1.451(2) . ?
C1 C10 1.543(2) . ?
C1 C8 1.548(2) . ?
C1 H1 0.9800 . ?
C2 O1 1.381(2) . ?
C2 C7 1.382(2) . ?
C2 C3 1.384(2) . ?
C3 C4 1.391(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.390(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.507(2) . ?
C8 C9 1.499(2) . ?
C8 H8 0.9800 . ?
C9 F2 1.336(2) . ?
C9 F3 1.340(2) . ?
C9 F1 1.341(2) . ?
C10 O2 1.2155(19) . ?
C10 C11 1.490(2) . ?
C11 C16 1.390(2) . ?
C11 C12 1.407(2) . ?
C12 C13 1.383(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.394(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
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
O1 C2 C3 C4 178.91(13) . . . . ?
C7 C2 C3 C4 -0.7(2) . . . . ?
C2 C3 C4 C5 1.2(2) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C7 -1.1(3) . . . . ?
O1 C2 C7 C6 179.63(13) . . . . ?
C3 C2 C7 C6 -0.7(2) . . . . ?
O1 C2 C7 C8 -0.18(16) . . . . ?
C3 C2 C7 C8 179.46(13) . . . . ?
C5 C6 C7 C2 1.6(2) . . . . ?
C5 C6 C7 C8 -178.62(16) . . . . ?
C2 C7 C8 C9 -116.65(14) . . . . ?
C6 C7 C8 C9 63.6(2) . . . . ?
C2 C7 C8 C1 4.17(14) . . . . ?
C6 C7 C8 C1 -175.60(16) . . . . ?
O1 C1 C8 C9 114.60(14) . . . . ?
C10 C1 C8 C9 -124.89(14) . . . . ?
O1 C1 C8 C7 -6.58(13) . . . . ?
C10 C1 C8 C7 113.94(13) . . . . ?
C7 C8 C9 F2 -66.22(17) . . . . ?
C1 C8 C9 F2 178.72(13) . . . . ?
C7 C8 C9 F3 174.03(13) . . . . ?
C1 C8 C9 F3 58.98(18) . . . . ?
C7 C8 C9 F1 53.81(18) . . . . ?
C1 C8 C9 F1 -61.24(18) . . . . ?
O1 C1 C10 O2 131.99(15) . . . . ?
C8 C1 C10 O2 12.61(19) . . . . ?
O1 C1 C10 C11 -48.10(16) . . . . ?
C8 C1 C10 C11 -167.48(12) . . . . ?
O2 C10 C11 C16 165.61(15) . . . . ?
C1 C10 C11 C16 -14.3(2) . . . . ?
O2 C10 C11 C12 -14.0(2) . . . . ?
C1 C10 C11 C12 166.09(13) . . . . ?
C16 C11 C12 C13 1.4(2) . . . . ?
C10 C11 C12 C13 -178.97(16) . . . . ?
C11 C12 C13 C14 -1.0(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C12 C11 C16 C15 -0.6(2) . . . . ?
C10 C11 C16 C15 179.76(15) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
C7 C2 O1 C1 -4.29(15) . . . . ?
C3 C2 O1 C1 176.08(13) . . . . ?
C10 C1 O1 C2 -116.17(12) . . . . ?
C8 C1 O1 C2 6.78(14) . . . . ?
