#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/25/1502550.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_1502550
loop_
_publ_author_name
'Morandi, Bill'
'Carreira, Erick M.'
_publ_section_title
;
 Expedient preparation of trifluoromethyl-substituted benzofuranols.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5984
_journal_page_last               5985
_journal_paper_doi               10.1021/ol202423s
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C11 H11 F3 O3'
_chemical_formula_weight         248.20
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.022(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3649(16)
_cell_length_b                   13.029(2)
_cell_length_c                   8.3029(10)
_cell_measurement_reflns_used    4354
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.33
_cell_measurement_theta_min      2.60
_cell_volume                     1060.0(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12508
_diffrn_reflns_theta_full        30.49
_diffrn_reflns_theta_max         30.49
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_correction_T_min  0.9632
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1345
_reflns_number_gt                2455
_reflns_number_total             3193
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol202423s_si_002.cif
_cod_data_source_block           ca040211_0ma
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1502550
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
F1 F 0.96634(8) 1.05346(6) 0.80046(11) 0.0278(2) Uani 1 1 d
F2 F 0.92813(8) 0.94293(6) 0.59778(10) 0.0247(2) Uani 1 1 d
F3 F 1.03924(8) 0.89795(7) 0.85554(10) 0.0284(2) Uani 1 1 d
O1 O 0.44908(9) 0.75521(7) 0.38927(11) 0.0186(2) Uani 1 1 d
O2 O 0.61210(10) 1.03254(7) 0.77819(11) 0.0195(2) Uani 1 1 d
O3 O 0.59498(9) 0.92134(6) 0.55156(11) 0.0171(2) Uani 1 1 d
C1 C 0.93378(13) 0.95442(10) 0.76099(15) 0.0194(3) Uani 1 1 d
C2 C 0.80178(12) 0.92630(9) 0.78910(15) 0.0155(2) Uani 1 1 d
C3 C 0.75655(13) 0.81742(9) 0.73701(15) 0.0154(2) Uani 1 1 d
C4 C 0.63739(12) 0.82317(9) 0.60235(14) 0.0144(2) Uani 1 1 d
C5 C 0.56512(12) 0.73682(9) 0.52178(15) 0.0151(2) Uani 1 1 d
C6 C 0.36982(14) 0.66730(10) 0.30689(16) 0.0193(3) Uani 1 1 d
C7 C 0.24678(14) 0.70747(11) 0.16862(17) 0.0236(3) Uani 1 1 d
C8 C 0.68193(12) 0.99168(9) 0.67640(14) 0.0155(2) Uani 1 1 d
C9 C 0.81107(13) 0.72244(10) 0.80213(16) 0.0195(3) Uani 1 1 d
C10 C 0.74050(14) 0.63519(10) 0.72394(16) 0.0204(3) Uani 1 1 d
C11 C 0.61953(13) 0.64150(10) 0.58538(16) 0.0181(3) Uani 1 1 d
H8 H 0.7099(15) 1.0462(11) 0.6105(18) 0.013(3) Uiso 1 1 d
H2A H 0.8167(17) 0.9407(12) 0.912(2) 0.023(4) Uiso 1 1 d
H9 H 0.894(2) 0.7160(13) 0.899(2) 0.030(4) Uiso 1 1 d
H10 H 0.7712(17) 0.5661(12) 0.763(2) 0.023(4) Uiso 1 1 d
H6A H 0.4234(16) 0.6239(13) 0.262(2) 0.024(4) Uiso 1 1 d
H6B H 0.3426(16) 0.6281(13) 0.393(2) 0.024(4) Uiso 1 1 d
H7A H 0.1850(18) 0.7507(14) 0.216(2) 0.040(5) Uiso 1 1 d
H11 H 0.5721(19) 0.5797(13) 0.528(2) 0.031(4) Uiso 1 1 d
H7B H 0.1875(17) 0.6501(13) 0.106(2) 0.025(4) Uiso 1 1 d
H7C H 0.2684(18) 0.7472(15) 0.084(2) 0.038(5) Uiso 1 1 d
H2 H 0.558(2) 1.0783(15) 0.722(2) 0.034(5) Uiso 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
C5 O1 C6 117.35(10)
C8 O2 H2 108.3(12)
C4 O3 C8 107.81(9)
F3 C1 F2 106.77(10)
F3 C1 F1 106.97(10)
F2 C1 F1 106.07(10)
F3 C1 C2 112.62(11)
F2 C1 C2 112.66(10)
F1 C1 C2 111.32(10)
C1 C2 C3 113.36(10)
C1 C2 C8 111.33(10)
C3 C2 C8 103.35(10)
C1 C2 H2A 105.4(10)
C3 C2 H2A 113.6(9)
C8 C2 H2A 110.0(9)
C4 C3 C9 120.53(11)
C4 C3 C2 107.15(10)
C9 C3 C2 132.30(12)
C3 C4 O3 114.47(10)
C3 C4 C5 123.15(11)
O3 C4 C5 122.38(11)
O1 C5 C11 127.21(11)
O1 C5 C4 116.13(10)
C11 C5 C4 116.66(11)
O1 C6 C7 107.17(11)
O1 C6 H6A 110.0(10)
C7 C6 H6A 111.3(10)
O1 C6 H6B 108.5(10)
C7 C6 H6B 111.1(9)
H6A C6 H6B 108.6(13)
C6 C7 H7A 112.1(10)
C6 C7 H7B 111.2(10)
H7A C7 H7B 105.0(14)
C6 C7 H7C 113.9(11)
H7A C7 H7C 108.1(15)
H7B C7 H7C 105.9(14)
O2 C8 O3 110.55(10)
O2 C8 C2 108.61(9)
O3 C8 C2 105.85(9)
O2 C8 H8 111.4(9)
O3 C8 H8 106.4(8)
C2 C8 H8 113.9(9)
C10 C9 C3 117.32(12)
C10 C9 H9 120.3(10)
C3 C9 H9 122.4(10)
C9 C10 C11 121.91(11)
C9 C10 H10 122.2(10)
C11 C10 H10 115.9(10)
C5 C11 C10 120.43(12)
C5 C11 H11 118.1(11)
C10 C11 H11 121.5(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C1 1.3469(16)
F2 C1 1.3455(14)
F3 C1 1.3390(15)
O1 C5 1.3608(15)
O1 C6 1.4451(14)
O2 C8 1.3857(14)
O2 H2 0.85(2)
O3 C4 1.3734(14)
O3 C8 1.4552(14)
C1 C2 1.5063(17)
C2 C3 1.5122(16)
C2 C8 1.5449(17)
C2 H2A 0.996(17)
C3 C4 1.3715(17)
C3 C9 1.3943(17)
C4 C5 1.3956(16)
C5 C11 1.3947(17)
C6 C7 1.5046(19)
C6 H6A 0.951(17)
C6 H6B 0.992(16)
C7 H7A 1.025(19)
C7 H7B 1.000(17)
C7 H7C 0.953(19)
C8 H8 0.996(15)
C9 C10 1.3925(19)
C9 H9 0.971(19)
C10 C11 1.4008(19)
C10 H10 0.976(16)
C11 H11 0.981(18)
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
F3 C1 C2 C3 -63.16(13)
F2 C1 C2 C3 57.68(14)
F1 C1 C2 C3 176.70(10)
F3 C1 C2 C8 -179.18(10)
F2 C1 C2 C8 -58.34(13)
F1 C1 C2 C8 60.68(13)
C1 C2 C3 C4 -114.63(11)
C8 C2 C3 C4 6.01(12)
C1 C2 C3 C9 67.07(16)
C8 C2 C3 C9 -172.29(12)
C9 C3 C4 O3 179.74(10)
C2 C3 C4 O3 1.20(13)
C9 C3 C4 C5 -0.80(18)
C2 C3 C4 C5 -179.34(10)
C8 O3 C4 C3 -8.47(13)
C8 O3 C4 C5 172.07(10)
C6 O1 C5 C11 2.03(17)
C6 O1 C5 C4 -178.07(10)
C3 C4 C5 O1 -179.59(10)
O3 C4 C5 O1 -0.18(16)
C3 C4 C5 C11 0.32(17)
O3 C4 C5 C11 179.73(10)
C5 O1 C6 C7 178.90(10)
C4 O3 C8 O2 -105.73(10)
C4 O3 C8 C2 11.71(11)
C1 C2 C8 O2 -129.90(10)
C3 C2 C8 O2 108.08(10)
C1 C2 C8 O3 111.36(11)
C3 C2 C8 O3 -10.65(11)
C4 C3 C9 C10 0.62(17)
C2 C3 C9 C10 178.73(12)
C3 C9 C10 C11 -0.01(18)
O1 C5 C11 C10 -179.79(11)
C4 C5 C11 C10 0.31(17)
C9 C10 C11 C5 -0.47(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139037509
