#------------------------------------------------------------------------------
#$Date: 2019-11-03 12:43:35 +0200 (Sun, 03 Nov 2019) $
#$Revision: 221423 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/83/4128300.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_4128300
loop_
_publ_author_name
'Belligund, Kavita'
'Mathew, Thomas'
'Hunt, Jonathan R.'
'Nirmalchandar, Archith'
'Haiges, Ralf'
'Dawlaty, Jahan'
'Prakash, G. K. Surya'
_publ_section_title
;
 Photochemistry of 2-Nitroarenes: 2-Nitrophenyl-α-trifluoromethyl
 Carbinols as Synthons for Fluoroorganics.
;
_journal_issue                   40
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15921
_journal_page_last               15931
_journal_paper_doi               10.1021/jacs.9b07241
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C16 H10 Br2 F6 N2 O6, 4(C2 H6 O S)'
_chemical_formula_sum            'C12 H17 Br F3 N O5 S2'
_chemical_formula_weight         456.29
_chemical_name_common            Kavita062518
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                112.364(4)
_cell_angle_beta                 98.218(4)
_cell_angle_gamma                101.891(4)
_cell_formula_units_Z            2
_cell_length_a                   9.414(3)
_cell_length_b                   9.426(3)
_cell_length_c                   11.441(4)
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      30.5438
_cell_measurement_theta_min      2.2800
_cell_volume                     890.8(5)
_computing_cell_refinement       'APEX3 v2018.1-0 (Bruker AXS, 2018)'
_computing_data_collection
'Bruker Instrument Service v2012.12.0.3 (Bruker AXS, 2012)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 2013)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  'SHELXTL XL 2017/1 (Bruker AXS, 2017)'
_computing_structure_refinement  'SHELXTL XL 2017/1 (Bruker AXS, 2017)'
_computing_structure_solution    'SHELXTL XT 2014/5 (Bruker AXS, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'
_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19993
_diffrn_reflns_theta_full        30.57
_diffrn_reflns_theta_max         30.57
_diffrn_reflns_theta_min         1.99
_diffrn_source                   'fine-focus tube'
_exptl_absorpt_coefficient_mu    2.593
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2 (Bruker AXS, 2016)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.508
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         5356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0227
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0186P)²+0.5577P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0519
_refine_ls_wR_factor_ref         0.0542
_reflns_number_gt                4825
_reflns_number_total             5356
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b07241_si_007.cif
_cod_data_source_block           Kavita062518
_cod_database_code               4128300
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.37680(13) 0.43844(15) 0.59393(12) 0.0122(2) Uani d . . . 1.0 . .
C C2 0.24927(14) 0.31536(15) 0.51364(12) 0.0144(2) Uani d . . . 1.0 . .
H H2 0.21719 0.295552 0.424861 0.017 Uiso calc U . R 1.0 . .
C C3 0.16931(14) 0.22177(15) 0.56431(12) 0.0151(2) Uani d . . . 1.0 . .
H H3 0.080878 0.138265 0.511381 0.018 Uiso calc U . R 1.0 . .
C C4 0.22083(14) 0.25232(15) 0.69370(12) 0.0143(2) Uani d . . . 1.0 . .
C C5 0.34603(14) 0.37767(15) 0.77532(12) 0.0139(2) Uani d . . . 1.0 . .
H H5 0.376861 0.397539 0.864245 0.017 Uiso calc U . R 1.0 . .
C C6 0.42667(13) 0.47472(14) 0.72579(11) 0.0121(2) Uani d . . . 1.0 . .
C C7 0.56352(14) 0.61283(15) 0.81948(12) 0.0129(2) Uani d . . . 1.0 . .
C C8 0.51039(15) 0.75592(16) 0.90065(13) 0.0177(2) Uani d . . . 1.0 . .
N N1 0.45086(12) 0.52826(12) 0.53001(10) 0.01210(19) Uani d . . . 1.0 . .
O O1 0.40921(11) 0.64394(11) 0.52074(9) 0.01746(18) Uani d . . . 1.0 . .
O O2 0.65158(11) 0.65940(12) 0.74552(9) 0.01615(18) Uani d . . . 1.0 . .
H H2A 0.729(2) 0.718(2) 0.7904(19) 0.024 Uiso d U . . 1.0 . .
O O3 0.63994(11) 0.57476(12) 0.91152(9) 0.01610(18) Uani d . . . 1.0 . .
H H3A 0.668(2) 0.496(2) 0.8700(19) 0.024 Uiso d U . . 1.0 . .
F F1 0.42226(10) 0.79660(10) 0.82348(9) 0.02349(18) Uani d . . . 1.0 . .
F F2 0.62662(10) 0.88450(10) 0.97369(8) 0.02462(18) Uani d . . . 1.0 . .
F F3 0.43180(11) 0.72414(11) 0.98136(8) 0.02618(19) Uani d . . . 1.0 . .
Br Br1 0.11978(2) 0.11262(2) 0.75805(2) 0.01982(4) Uani d . . . 1.0 . .
S S1 0.63696(4) 0.17830(4) 0.67778(4) 0.02175(7) Uani d . . . 1.0 . .
C C9 0.6481(2) 0.01866(19) 0.72362(18) 0.0327(4) Uani d . . . 1.0 . .
H H9A 0.591138 -0.083813 0.650867 0.049 Uiso calc U . R 1.0 . .
H H9B 0.606173 0.032263 0.799526 0.049 Uiso calc U . R 1.0 . .
H H9C 0.753024 0.020081 0.745566 0.049 Uiso calc U . R 1.0 . .
C C10 0.74114(18) 0.1346(2) 0.55664(15) 0.0264(3) Uani d . . . 1.0 . .
H H10A 0.689057 0.029142 0.485452 0.04 Uiso calc U . R 1.0 . .
H H10B 0.840934 0.134417 0.595299 0.04 Uiso calc U . R 1.0 . .
H H10C 0.75076 0.216073 0.522531 0.04 Uiso calc U . R 1.0 . .
O O4 0.73730(12) 0.32907(12) 0.79100(11) 0.0251(2) Uani d . . . 1.0 . .
S S2 0.06785(4) 0.78759(4) 0.84587(4) 0.02362(8) Uani d . . . 1.0 . .
C C11 0.0331(6) 0.6657(13) 0.9414(8) 0.0316(15) Uani d . P . 0.456(16) A 1
H H11A 0.011522 0.730415 1.023222 0.047 Uiso calc U P R 0.456(16) A 1
H H11B 0.122178 0.632212 0.960637 0.047 Uiso calc U P R 0.456(16) A 1
H H11C -0.052451 0.570959 0.890257 0.047 Uiso calc U P R 0.456(16) A 1
C C12 0.0621(10) 0.6305(12) 0.7026(6) 0.0346(15) Uani d . P . 0.456(16) A 1
H H12A -0.036282 0.551246 0.671432 0.052 Uiso calc U P R 0.456(16) A 1
H H12B 0.140004 0.580597 0.718122 0.052 Uiso calc U P R 0.456(16) A 1
H H12C 0.079142 0.670511 0.636762 0.052 Uiso calc U P R 0.456(16) A 1
C C11A 0.0554(6) 0.7462(13) 0.9764(6) 0.0351(14) Uani d . P . 0.544(16) A 2
H H11D 0.066317 0.845153 1.052861 0.053 Uiso calc U P R 0.544(16) A 2
H H11E 0.135051 0.698911 0.993486 0.053 Uiso calc U P R 0.544(16) A 2
H H11F -0.04224 0.670464 0.958299 0.053 Uiso calc U P R 0.544(16) A 2
C C12A 0.0248(8) 0.5872(8) 0.7174(7) 0.0364(13) Uani d . P . 0.544(16) A 2
H H12D -0.070746 0.521851 0.717338 0.055 Uiso calc U P R 0.544(16) A 2
H H12E 0.104352 0.538909 0.732491 0.055 Uiso calc U P R 0.544(16) A 2
H H12F 0.017721 0.592603 0.632964 0.055 Uiso calc U P R 0.544(16) A 2
O O5 -0.06894(12) 0.84287(13) 0.82096(12) 0.0266(2) Uani d . . . 1.0 . .
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'
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'
Br Br -0.2901 2.4595 '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'
H H 0.0000 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 C6 . . 122.51(11)
C2 C1 N1 . . 114.35(11)
C6 C1 N1 . . 123.13(11)
C3 C2 C1 . . 119.38(11)
C3 C2 H2 . . 120.3
C1 C2 H2 . . 120.3
C2 C3 C4 . . 118.75(12)
C2 C3 H3 . . 120.6
C4 C3 H3 . . 120.6
C3 C4 C5 . . 122.14(11)
C3 C4 Br1 . . 118.32(10)
C5 C4 Br1 . . 119.50(9)
C4 C5 C6 . . 119.65(11)
C4 C5 H5 . . 120.2
C6 C5 H5 . . 120.2
C1 C6 C5 . . 117.51(11)
C1 C6 C7 . . 124.48(11)
C5 C6 C7 . . 118.01(11)
O2 C7 O3 . . 113.99(11)
O2 C7 C6 . . 108.10(10)
O3 C7 C6 . . 112.35(10)
O2 C7 C8 . . 108.60(10)
O3 C7 C8 . . 104.46(10)
C6 C7 C8 . . 109.16(10)
F2 C8 F1 . . 107.48(11)
F2 C8 F3 . . 107.35(11)
F1 C8 F3 . . 107.07(11)
F2 C8 C7 . . 111.04(11)
F1 C8 C7 . . 111.15(11)
F3 C8 C7 . . 112.49(11)
O1 N1 N1 . 2_666 122.12(13)
O1 N1 C1 . . 120.92(10)
N1 N1 C1 2_666 . 116.48(12)
C7 O2 H2A . . 109.8(14)
C7 O3 H3A . . 106.6(13)
O4 S1 C10 . . 105.14(8)
O4 S1 C9 . . 105.66(8)
C10 S1 C9 . . 98.21(8)
S1 C9 H9A . . 109.5
S1 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
S1 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
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
O5 S2 C11A . . 104.39(17)
O5 S2 C12 . . 106.9(2)
O5 S2 C12A . . 104.8(2)
C11A S2 C12A . . 100.7(2)
O5 S2 C11 . . 108.70(18)
C12 S2 C11 . . 96.3(3)
S2 C11 H11A . . 109.5
S2 C11 H11B . . 109.5
H11A C11 H11B . . 109.5
S2 C11 H11C . . 109.5
H11A C11 H11C . . 109.5
H11B C11 H11C . . 109.5
S2 C12 H12A . . 109.5
S2 C12 H12B . . 109.5
H12A C12 H12B . . 109.5
S2 C12 H12C . . 109.5
H12A C12 H12C . . 109.5
H12B C12 H12C . . 109.5
S2 C11A H11D . . 109.5
S2 C11A H11E . . 109.5
H11D C11A H11E . . 109.5
S2 C11A H11F . . 109.5
H11D C11A H11F . . 109.5
H11E C11A H11F . . 109.5
S2 C12A H12D . . 109.5
S2 C12A H12E . . 109.5
H12D C12A H12E . . 109.5
S2 C12A H12F . . 109.5
H12D C12A H12F . . 109.5
H12E C12A H12F . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.3895(17)
C1 C6 . 1.3972(17)
C1 N1 . 1.4531(16)
C2 C3 . 1.3861(18)
C2 H2 . 0.95
C3 C4 . 1.3864(18)
C3 H3 . 0.95
C4 C5 . 1.3889(18)
C4 Br1 . 1.8982(13)
C5 C6 . 1.4020(17)
C5 H5 . 0.95
C6 C7 . 1.5348(17)
C7 O2 . 1.3890(15)
C7 O3 . 1.3901(15)
C7 C8 . 1.5458(18)
C8 F2 . 1.3364(15)
C8 F1 . 1.3395(16)
C8 F3 . 1.3432(16)
N1 O1 . 1.2674(14)
N1 N1 2_666 1.311(2)
O2 H2A . 0.78(2)
O3 H3A . 0.84(2)
S1 O4 . 1.5120(11)
S1 C10 . 1.7813(16)
S1 C9 . 1.7888(17)
C9 H9A . 0.98
C9 H9B . 0.98
C9 H9C . 0.98
C10 H10A . 0.98
C10 H10B . 0.98
C10 H10C . 0.98
S2 O5 . 1.5152(12)
S2 C11A . 1.694(4)
S2 C12 . 1.725(7)
S2 C12A . 1.815(6)
S2 C11 . 1.877(6)
C11 H11A . 0.98
C11 H11B . 0.98
C11 H11C . 0.98
C12 H12A . 0.98
C12 H12B . 0.98
C12 H12C . 0.98
C11A H11D . 0.98
C11A H11E . 0.98
C11A H11F . 0.98
C12A H12D . 0.98
C12A H12E . 0.98
C12A H12F . 0.98
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_site_symmetry_4
_geom_torsion
C6 C1 C2 C3 . -1.49(19)
N1 C1 C2 C3 . -179.89(11)
C1 C2 C3 C4 . -1.10(19)
C2 C3 C4 C5 . 2.8(2)
C2 C3 C4 Br1 . -174.98(10)
C3 C4 C5 C6 . -1.88(19)
Br1 C4 C5 C6 . 175.86(9)
C2 C1 C6 C5 . 2.38(18)
N1 C1 C6 C5 . -179.37(11)
C2 C1 C6 C7 . -177.81(12)
N1 C1 C6 C7 . 0.44(19)
C4 C5 C6 C1 . -0.69(18)
C4 C5 C6 C7 . 179.48(11)
C1 C6 C7 O2 . -18.33(16)
C5 C6 C7 O2 . 161.48(11)
C1 C6 C7 O3 . -144.98(12)
C5 C6 C7 O3 . 34.83(15)
C1 C6 C7 C8 . 99.63(14)
C5 C6 C7 C8 . -80.56(14)
O2 C7 C8 F2 . -55.81(14)
O3 C7 C8 F2 . 66.18(13)
C6 C7 C8 F2 . -173.46(10)
O2 C7 C8 F1 . 63.79(13)
O3 C7 C8 F1 . -174.22(10)
C6 C7 C8 F1 . -53.86(13)
O2 C7 C8 F3 . -176.15(10)
O3 C7 C8 F3 . -54.16(14)
C6 C7 C8 F3 . 66.20(14)
C2 C1 N1 O1 . 85.13(14)
C6 C1 N1 O1 . -93.26(15)
C2 C1 N1 N1 2_666 -87.05(16)
C6 C1 N1 N1 2_666 94.57(16)
