#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/32/1513243.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_1513243
loop_
_publ_author_name
'Liu, Xiao'
'Pan, Ling'
'Dong, Jinhuan'
'Xu, Xianxiu'
'Zhang, Qian'
'Liu, Qun'
_publ_section_title
;
 1,3-Carbothiolation of 4-(Trifluoromethyl)-p-Quinols: A New Access to
 Functionalized (Trifluoromethyl)arenes.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6242
_journal_page_last               6245
_journal_paper_doi               10.1021/ol403096g
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C16 H13 F3 O S'
_chemical_formula_sum            'C16 H13 F3 O S'
_chemical_formula_weight         310.32
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.211(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2750(3)
_cell_length_b                   5.21000(10)
_cell_length_c                   30.1440(8)
_cell_measurement_reflns_used    2192
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.9796
_cell_measurement_theta_min      4.3999
_cell_volume                     1455.56(7)
_computing_cell_refinement       CrysAlis
_computing_data_collection       'CrysAlis (Oxford Diffraction, 2006)'
_computing_data_reduction        CrysAlis
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            5691
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.12
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.9754
_exptl_absorpt_correction_T_min  0.9516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis (Oxford Diffraction, 2006)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0665
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1186P)²+0.2355P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1800
_refine_ls_wR_factor_ref         0.2036
_reflns_number_gt                1952
_reflns_number_total             2554
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol403096g_si_002.cif
_cod_data_source_block           p21n
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1513243
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_refinement_flags
C1 C 0.7866(3) 0.6130(5) 0.10102(9) 0.0533(7) Uani 1 1 d .
H1 H 0.7459 0.7187 0.1220 0.064 Uiso 1 1 calc R
C2 C 0.7263(3) 0.6074(5) 0.05765(9) 0.0554(7) Uani 1 1 d .
C3 C 0.7878(4) 0.4487(6) 0.02691(10) 0.0637(8) Uani 1 1 d .
H3 H 0.7485 0.4411 -0.0019 0.076 Uiso 1 1 calc R
C4 C 0.9065(4) 0.3020(6) 0.03847(10) 0.0616(8) Uani 1 1 d .
H4 H 0.9471 0.1971 0.0173 0.074 Uiso 1 1 calc R
C5 C 0.9666(3) 0.3089(5) 0.08153(9) 0.0512(6) Uani 1 1 d .
C6 C 0.9055(3) 0.4646(5) 0.11334(8) 0.0485(6) Uani 1 1 d .
C7 C 0.9617(3) 0.4759(5) 0.16093(9) 0.0532(7) Uani 1 1 d .
H7A H 0.9331 0.6382 0.1737 0.064 Uiso 1 1 calc R
H7B H 1.0663 0.4712 0.1614 0.064 Uiso 1 1 calc R
C8 C 0.9080(3) 0.2591(5) 0.18959(9) 0.0490(6) Uani 1 1 d .
C9 C 0.9748(3) 0.2253(5) 0.23531(9) 0.0523(7) Uani 1 1 d .
C10 C 1.0837(4) 0.3820(7) 0.25187(10) 0.0664(8) Uani 1 1 d .
H10 H 1.1182 0.5138 0.2344 0.080 Uiso 1 1 calc R
C11 C 1.1422(5) 0.3447(8) 0.29441(12) 0.0819(11) Uani 1 1 d .
H11 H 1.2151 0.4524 0.3054 0.098 Uiso 1 1 calc R
C12 C 1.0933(5) 0.1509(9) 0.32017(11) 0.0835(12) Uani 1 1 d .
H12 H 1.1334 0.1252 0.3486 0.100 Uiso 1 1 calc R
C13 C 0.9840(5) -0.0071(8) 0.30406(12) 0.0842(12) Uani 1 1 d .
H13 H 0.9507 -0.1394 0.3217 0.101 Uiso 1 1 calc R
C14 C 0.9233(4) 0.0302(7) 0.26167(10) 0.0683(8) Uani 1 1 d .
H14 H 0.8487 -0.0751 0.2511 0.082 Uiso 1 1 calc R
C15 C 0.5531(4) 1.0135(7) 0.08226(13) 0.0790(10) Uani 1 1 d .
H15A H 0.4712 1.1201 0.0749 0.119 Uiso 1 1 calc R
H15B H 0.6382 1.1181 0.0853 0.119 Uiso 1 1 calc R
H15C H 0.5381 0.9264 0.1098 0.119 Uiso 1 1 calc R
C16 C 1.1011(4) 0.1598(7) 0.09139(10) 0.0635(8) Uani 1 1 d .
O1 O 0.8127(3) 0.1172(5) 0.17607(7) 0.0706(6) Uani 1 1 d .
F1 F 1.2166(2) 0.3111(5) 0.09725(9) 0.0981(8) Uani 1 1 d .
F2 F 1.0967(2) 0.0166(4) 0.12838(7) 0.0868(7) Uani 1 1 d .
F3 F 1.1342(3) -0.0035(5) 0.05940(8) 0.1088(9) Uani 1 1 d .
S1 S 0.57519(11) 0.78468(19) 0.03959(3) 0.0852(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'
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
C6 C1 C2 121.5(3)
C6 C1 H1 119.2
C2 C1 H1 119.2
C3 C2 C1 118.5(3)
C3 C2 S1 117.0(2)
C1 C2 S1 124.4(2)
C4 C3 C2 120.7(3)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 120.7(3)
C3 C4 H4 119.7
C5 C4 H4 119.7
C6 C5 C4 119.8(3)
C6 C5 C16 121.7(2)
C4 C5 C16 118.3(2)
C1 C6 C5 118.8(2)
C1 C6 C7 118.4(2)
C5 C6 C7 122.9(2)
C6 C7 C8 113.8(2)
C6 C7 H7A 108.8
C8 C7 H7A 108.8
C6 C7 H7B 108.8
C8 C7 H7B 108.8
H7A C7 H7B 107.7
O1 C8 C9 120.5(2)
O1 C8 C7 120.9(2)
C9 C8 C7 118.5(2)
C10 C9 C14 119.4(3)
C10 C9 C8 122.3(3)
C14 C9 C8 118.3(3)
C9 C10 C11 120.5(3)
C9 C10 H10 119.8
C11 C10 H10 119.8
C12 C11 C10 120.3(4)
C12 C11 H11 119.9
C10 C11 H11 119.9
C11 C12 C13 119.9(3)
C11 C12 H12 120.1
C13 C12 H12 120.1
C12 C13 C14 120.4(4)
C12 C13 H13 119.8
C14 C13 H13 119.8
C9 C14 C13 119.6(4)
C9 C14 H14 120.2
C13 C14 H14 120.2
S1 C15 H15A 109.5
S1 C15 H15B 109.5
H15A C15 H15B 109.5
S1 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
F3 C16 F1 105.4(3)
F3 C16 F2 105.2(3)
F1 C16 F2 105.5(3)
F3 C16 C5 113.8(2)
F1 C16 C5 112.3(3)
F2 C16 C5 113.8(3)
C2 S1 C15 104.07(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.385(4)
C1 C2 1.402(4)
C1 H1 0.9300
C2 C3 1.382(4)
C2 S1 1.748(3)
C3 C4 1.373(5)
C3 H3 0.9300
C4 C5 1.393(4)
C4 H4 0.9300
C5 C6 1.393(4)
C5 C16 1.490(4)
C6 C7 1.509(4)
C7 C8 1.518(4)
C7 H7A 0.9700
C7 H7B 0.9700
C8 O1 1.211(3)
C8 C9 1.500(4)
C9 C10 1.377(5)
C9 C14 1.386(4)
C10 C11 1.387(5)
C10 H10 0.9300
C11 C12 1.362(6)
C11 H11 0.9300
C12 C13 1.379(6)
C12 H12 0.9300
C13 C14 1.390(5)
C13 H13 0.9300
C14 H14 0.9300
C15 S1 1.772(4)
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 F3 1.331(4)
C16 F1 1.337(4)
C16 F2 1.343(4)
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
C6 C1 C2 C3 0.2(4)
C6 C1 C2 S1 179.1(2)
C1 C2 C3 C4 -0.8(5)
S1 C2 C3 C4 -179.7(3)
C2 C3 C4 C5 0.5(5)
C3 C4 C5 C6 0.4(5)
C3 C4 C5 C16 -175.9(3)
C2 C1 C6 C5 0.7(4)
C2 C1 C6 C7 -178.4(3)
C4 C5 C6 C1 -1.0(4)
C16 C5 C6 C1 175.2(3)
C4 C5 C6 C7 178.1(3)
C16 C5 C6 C7 -5.8(4)
C1 C6 C7 C8 97.2(3)
C5 C6 C7 C8 -81.8(3)
C6 C7 C8 O1 -10.3(4)
C6 C7 C8 C9 170.2(2)
O1 C8 C9 C10 179.8(3)
C7 C8 C9 C10 -0.7(4)
O1 C8 C9 C14 -0.8(4)
C7 C8 C9 C14 178.7(3)
C14 C9 C10 C11 0.4(5)
C8 C9 C10 C11 179.8(3)
C9 C10 C11 C12 0.5(5)
C10 C11 C12 C13 -0.7(6)
C11 C12 C13 C14 -0.1(6)
C10 C9 C14 C13 -1.1(5)
C8 C9 C14 C13 179.5(3)
C12 C13 C14 C9 1.0(5)
C6 C5 C16 F3 171.8(3)
C4 C5 C16 F3 -12.0(4)
C6 C5 C16 F1 -68.5(4)
C4 C5 C16 F1 107.7(3)
C6 C5 C16 F2 51.3(4)
C4 C5 C16 F2 -132.5(3)
C3 C2 S1 C15 -166.9(3)
C1 C2 S1 C15 14.2(3)
