#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/39/1513948.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_1513948
loop_
_publ_author_name
'Xie, Jin'
'Yuan, Xiangai'
'Abdukader, Ablimit'
'Zhu, Chengjian'
'Ma, Jing'
_publ_section_title
;
 Visible-light-promoted radical C-h trifluoromethylation of free anilines.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1768
_journal_page_last               1771
_journal_paper_doi               10.1021/ol500469a
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C8 H8 F3 N O2 S'
_chemical_formula_weight         239.21
_chemical_name_common            4-(methylsulfonyl)-2-(trifluoromethyl)aniline
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.9680(16)
_cell_length_b                   15.300(3)
_cell_length_c                   16.954(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     2066.9(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Nonius cad4'
_diffrn_measurement_method       ω/2θ
_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  0.0744
_diffrn_reflns_av_sigmaI/netI    0.0729
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3664
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         3.12
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_T_max  0.9672
_exptl_absorpt_correction_T_min  0.9059
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0590
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1537
_refine_ls_wR_factor_ref         0.1802
_reflns_number_gt                1124
_reflns_number_total             1874
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol500469a_si_001.cif
_cod_data_source_block           b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1513948
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S S 0.11692(13) 0.01074(6) 0.34682(7) 0.0718(5) Uani 1 1 d .
N N -0.2211(5) 0.35378(19) 0.3508(2) 0.0759(10) Uani 1 1 d .
H0A H -0.1861 0.3937 0.3191 0.091 Uiso 1 1 calc R
H0B H -0.3026 0.3646 0.3826 0.091 Uiso 1 1 calc R
F1 F -0.3761(4) 0.14879(19) 0.49898(18) 0.1134(11) Uani 1 1 d .
O1 O 0.1408(5) -0.0137(2) 0.2661(2) 0.1198(14) Uani 1 1 d .
C1 C 0.3144(6) 0.0303(3) 0.3878(4) 0.0952(15) Uani 1 1 d .
H1B H 0.3773 -0.0231 0.3891 0.143 Uiso 1 1 calc R
H1C H 0.3014 0.0524 0.4404 0.143 Uiso 1 1 calc R
H1D H 0.3730 0.0726 0.3563 0.143 Uiso 1 1 calc R
F2 F -0.3179(4) 0.28492(19) 0.50590(16) 0.1020(10) Uani 1 1 d .
C2 C 0.0154(5) 0.1119(2) 0.3476(2) 0.0530(9) Uani 1 1 d .
O2 O 0.0293(4) -0.04852(17) 0.3982(2) 0.0991(11) Uani 1 1 d .
F3 F -0.4823(3) 0.23779(19) 0.41808(16) 0.0943(9) Uani 1 1 d .
C3 C -0.1136(4) 0.1260(2) 0.3999(2) 0.0528(9) Uani 1 1 d .
H3A H -0.1448 0.0819 0.4347 0.063 Uiso 1 1 calc R
C4 C -0.1980(4) 0.2056(2) 0.40150(19) 0.0475(8) Uani 1 1 d .
C5 C -0.1476(4) 0.2736(2) 0.3507(2) 0.0525(9) Uani 1 1 d .
C6 C -0.0149(5) 0.2569(2) 0.2986(2) 0.0669(11) Uani 1 1 d .
H6A H 0.0204 0.3010 0.2646 0.080 Uiso 1 1 calc R
C7 C 0.0636(5) 0.1780(3) 0.2964(2) 0.0660(11) Uani 1 1 d .
H7A H 0.1499 0.1683 0.2605 0.079 Uiso 1 1 calc R
C8 C -0.3416(5) 0.2186(2) 0.4561(2) 0.0645(10) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S 0.0705(7) 0.0478(6) 0.0972(9) -0.0193(5) 0.0042(6) 0.0008(5)
N 0.084(2) 0.0513(18) 0.093(2) 0.0195(17) 0.009(2) 0.0082(16)
F1 0.110(2) 0.107(2) 0.123(2) 0.0529(18) 0.0617(18) 0.0251(16)
O1 0.147(4) 0.098(2) 0.114(3) -0.053(2) -0.002(2) 0.029(2)
C1 0.072(3) 0.073(3) 0.141(4) 0.006(3) -0.008(3) 0.006(2)
F2 0.0883(18) 0.125(2) 0.0924(19) -0.0433(17) 0.0211(14) 0.0081(15)
C2 0.059(2) 0.0450(18) 0.056(2) -0.0074(15) 0.0022(18) -0.0025(16)
O2 0.087(2) 0.0435(13) 0.167(3) 0.0084(18) 0.010(2) -0.0102(14)
F3 0.0555(14) 0.111(2) 0.116(2) 0.0112(16) 0.0048(14) 0.0059(13)
C3 0.061(2) 0.0427(16) 0.055(2) 0.0063(15) 0.0004(18) -0.0101(16)
C4 0.0517(18) 0.0459(17) 0.0448(17) 0.0014(15) 0.0007(15) -0.0072(15)
C5 0.059(2) 0.0469(17) 0.0520(19) 0.0046(15) -0.0043(17) -0.0048(15)
C6 0.076(3) 0.059(2) 0.065(2) 0.0154(18) 0.014(2) -0.007(2)
C7 0.072(3) 0.068(2) 0.058(2) -0.001(2) 0.0237(19) -0.005(2)
C8 0.063(2) 0.065(2) 0.065(2) 0.008(2) 0.004(2) 0.0063(18)
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'
N N 0.0061 0.0033 '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
O1 S O2 118.6(2)
O1 S C1 107.8(3)
O2 S C1 107.8(2)
O1 S C2 107.5(2)
O2 S C2 109.23(18)
C1 S C2 105.2(2)
C5 N H0A 120.0
C5 N H0B 120.0
H0A N H0B 120.0
S C1 H1B 109.5
S C1 H1C 109.5
H1B C1 H1C 109.5
S C1 H1D 109.5
H1B C1 H1D 109.5
H1C C1 H1D 109.5
C3 C2 C7 119.7(3)
C3 C2 S 119.4(3)
C7 C2 S 120.9(3)
C2 C3 C4 120.8(3)
C2 C3 H3A 119.6
C4 C3 H3A 119.6
C3 C4 C5 119.8(3)
C3 C4 C8 120.1(3)
C5 C4 C8 120.1(3)
N C5 C6 119.4(3)
N C5 C4 122.8(3)
C6 C5 C4 117.8(3)
C7 C6 C5 121.7(3)
C7 C6 H6A 119.1
C5 C6 H6A 119.1
C6 C7 C2 120.2(3)
C6 C7 H7A 119.9
C2 C7 H7A 119.9
F1 C8 F3 105.7(3)
F1 C8 F2 107.3(3)
F3 C8 F2 105.0(3)
F1 C8 C4 113.3(3)
F3 C8 C4 112.2(3)
F2 C8 C4 112.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S O1 1.431(4)
S O2 1.438(3)
S C1 1.746(5)
S C2 1.746(3)
N C5 1.360(4)
N H0A 0.8600
N H0B 0.8600
F1 C8 1.321(4)
C1 H1B 0.9600
C1 H1C 0.9600
C1 H1D 0.9600
F2 C8 1.333(4)
C2 C3 1.375(5)
C2 C7 1.386(5)
F3 C8 1.326(4)
C3 C4 1.390(4)
C3 H3A 0.9300
C4 C5 1.410(4)
C4 C8 1.485(5)
C5 C6 1.400(5)
C6 C7 1.361(5)
C6 H6A 0.9300
C7 H7A 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
O1 S C2 C3 137.2(3)
O2 S C2 C3 7.3(4)
C1 S C2 C3 -108.1(3)
O1 S C2 C7 -43.0(4)
O2 S C2 C7 -173.0(3)
C1 S C2 C7 71.6(4)
C7 C2 C3 C4 0.9(5)
S C2 C3 C4 -179.4(3)
C2 C3 C4 C5 -2.0(5)
C2 C3 C4 C8 177.5(3)
C3 C4 C5 N -177.9(3)
C8 C4 C5 N 2.5(5)
C3 C4 C5 C6 1.5(5)
C8 C4 C5 C6 -178.0(3)
N C5 C6 C7 179.6(4)
C4 C5 C6 C7 0.1(6)
C5 C6 C7 C2 -1.3(6)
C3 C2 C7 C6 0.8(6)
S C2 C7 C6 -178.9(3)
C3 C4 C8 F1 -0.7(5)
C5 C4 C8 F1 178.8(3)
C3 C4 C8 F3 -120.3(4)
C5 C4 C8 F3 59.3(4)
C3 C4 C8 F2 121.4(4)
C5 C4 C8 F2 -59.1(5)
