#------------------------------------------------------------------------------
#$Date: 2019-11-25 20:19:37 +0200 (Mon, 25 Nov 2019) $
#$Revision: 241726 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/15/4131536.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_4131536
loop_
_publ_author_name
'Zhang, Hu'
'Buchwald, Stephen L.'
_publ_section_title
;
 Palladium-Catalyzed Negishi Coupling of α-CF₃ Oxiranyl
 Zincate: Access to Chiral CF₃-Substituted Benzylic Tertiary
 Alcohols.
;
_journal_issue                   33
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11590
_journal_page_last               11594
_journal_paper_doi               10.1021/jacs.7b06630
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C10 H9 F3 O S'
_chemical_formula_weight         234.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.017(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1870(13)
_cell_length_b                   5.4348(8)
_cell_length_c                   11.5306(18)
_cell_measurement_reflns_used    5204
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.42
_cell_measurement_theta_min      2.51
_cell_volume                     508.04(14)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8816
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.567
_diffrn_reflns_theta_min         1.784
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.577
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.185
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
; 
 Flack x determined using 1152 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.08(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2825
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0279
_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)+(0.0394P)²+0.0720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0695
_reflns_Friedel_coverage         0.802
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                2732
_reflns_number_total             2825
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b06630_si_001.cif
_cod_data_source_block           x17088
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4131536
_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   0.832
_shelx_estimated_absorpt_t_max   0.941
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
O1 O 0.49807(14) 0.5172(4) 0.13954(11) 0.0270(3) Uani 1 1 d . .
C1 C 0.4323(2) 0.7628(4) 0.11478(17) 0.0262(4) Uani 1 1 d . .
H1A H 0.4010 0.8102 0.0318 0.031 Uiso 1 1 calc R U
H1B H 0.4766 0.8981 0.1675 0.031 Uiso 1 1 calc R U
C2 C 0.3345(2) 0.5709(4) 0.16285(15) 0.0190(4) Uani 1 1 d . .
C3 C 0.2050(2) 0.4390(4) 0.07932(16) 0.0232(4) Uani 1 1 d . .
F1 F 0.19286(18) 0.2024(3) 0.10939(11) 0.0339(3) Uani 1 1 d . .
F2 F 0.05622(13) 0.5411(3) 0.08090(10) 0.0298(3) Uani 1 1 d . .
F3 F 0.23546(16) 0.4440(3) -0.03160(10) 0.0327(3) Uani 1 1 d . .
C4 C 0.3068(2) 0.5661(3) 0.28868(15) 0.0170(4) Uani 1 1 d . .
C5 C 0.3736(2) 0.3757(4) 0.36150(16) 0.0183(4) Uani 1 1 d . .
H5 H 0.4378 0.2517 0.3313 0.022 Uiso 1 1 calc R U
C6 C 0.3470(2) 0.3659(4) 0.47771(16) 0.0180(4) Uani 1 1 d . .
H6 H 0.3928 0.2354 0.5266 0.022 Uiso 1 1 calc R U
C7 C 0.25257(19) 0.5482(4) 0.52309(14) 0.0161(4) Uani 1 1 d . .
C8 C 0.1859(2) 0.7393(4) 0.45044(16) 0.0185(4) Uani 1 1 d . .
H8 H 0.1216 0.8635 0.4804 0.022 Uiso 1 1 calc R U
C9 C 0.2136(2) 0.7477(4) 0.33383(16) 0.0189(4) Uani 1 1 d . .
H9 H 0.1685 0.8785 0.2848 0.023 Uiso 1 1 calc R U
S1 S 0.22700(5) 0.51552(9) 0.67154(3) 0.01884(11) Uani 1 1 d . .
C10 C 0.1287(3) 0.7967(4) 0.70485(18) 0.0282(5) Uani 1 1 d . .
H10A H 0.1964 0.9367 0.6872 0.042 Uiso 1 1 calc R U
H10B H 0.1160 0.7991 0.7881 0.042 Uiso 1 1 calc R U
H10C H 0.0198 0.8078 0.6574 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'
S S 0.1246 0.1234 '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 O1 C1 61.24(13)
O1 C1 C2 58.69(12)
O1 C1 H1A 117.9
C2 C1 H1A 117.9
O1 C1 H1B 117.9
C2 C1 H1B 117.9
H1A C1 H1B 115.1
O1 C2 C1 60.06(14)
O1 C2 C4 116.72(14)
C1 C2 C4 122.76(17)
O1 C2 C3 112.04(16)
C1 C2 C3 117.86(16)
C4 C2 C3 114.91(15)
F3 C3 F1 107.31(17)
F3 C3 F2 107.19(15)
F1 C3 F2 107.07(17)
F3 C3 C2 113.11(16)
F1 C3 C2 111.19(16)
F2 C3 C2 110.68(17)
C9 C4 C5 119.35(16)
C9 C4 C2 120.95(16)
C5 C4 C2 119.69(16)
C6 C5 C4 120.52(17)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C7 120.15(17)
C5 C6 H6 119.9
C7 C6 H6 119.9
C8 C7 C6 119.43(16)
C8 C7 S1 124.62(14)
C6 C7 S1 115.95(14)
C9 C8 C7 120.00(16)
C9 C8 H8 120.0
C7 C8 H8 120.0
C4 C9 C8 120.55(17)
C4 C9 H9 119.7
C8 C9 H9 119.7
C7 S1 C10 103.87(10)
S1 C10 H10A 109.5
S1 C10 H10B 109.5
H10A C10 H10B 109.5
S1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.432(2)
O1 C1 1.453(3)
C1 C2 1.470(3)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C4 1.500(2)
C2 C3 1.510(3)
C3 F3 1.337(2)
C3 F1 1.339(3)
C3 F2 1.341(2)
C4 C9 1.392(3)
C4 C5 1.396(3)
C5 C6 1.388(3)
C5 H5 0.9500
C6 C7 1.402(3)
C6 H6 0.9500
C7 C8 1.397(3)
C7 S1 1.7622(17)
C8 C9 1.395(2)
C8 H8 0.9500
C9 H9 0.9500
S1 C10 1.793(2)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
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
C1 H1A O1 0.99 2.51 3.362(2) 143.9 2_655
