#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/52/2225254.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2225254
loop_
_publ_author_name
'Boechat, Núbia'
'dos Santos Lages, Adriana'
'Kover, Warner B.'
'Tiekink, Edward R. T.'
'Wardell, James L.'
'Wardell, Solange M. S. V.'
_publ_section_title
N-(4-Chlorophenyl)-1,1,1-trifluoro-N-(trifluoromethylsulfonyl)methanesulfonamide
_journal_coeditor_code           HB5319
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o506
_journal_page_last               o507
_journal_paper_doi               10.1107/S1600536810003326
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H4 Cl F6 N O4 S2'
_chemical_formula_moiety         'C8 H4 Cl F6 N O4 S2'
_chemical_formula_sum            'C8 H4 Cl F6 N O4 S2'
_chemical_formula_weight         391.70
_chemical_name_systematic
;
N-(4-Chlorophenyl)-1,1,1-trifluoro-N-
(trifluoromethylsulfonyl)methanesulfonamide
;
_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
_cell_angle_beta                 108.014(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5998(3)
_cell_length_b                   13.4423(4)
_cell_length_c                   9.0548(2)
_cell_measurement_reflns_used    2983
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     1342.69(6)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_av_sigmaI/netI    0.019
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17100
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.9
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.938
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.62
_refine_diff_density_min         -0.41
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.034
_refine_ls_R_factor_gt           0.031
_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)+(0.0407P)²+1.1662P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.080
_refine_ls_wR_factor_ref         0.082
_reflns_number_gt                2806
_reflns_number_total             3047
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5319.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225254
_cod_database_fobs_code          2225254
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_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
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.97286(4) 0.86092(3) 0.34987(5) 0.02733(12) Uani d . 1 . .
S S1 0.78053(4) 1.09197(3) 0.91222(4) 0.01889(11) Uani d . 1 . .
S S2 0.59031(4) 0.94255(3) 0.78741(5) 0.01943(11) Uani d . 1 . .
F F1 0.70006(16) 1.20000(9) 0.66292(14) 0.0497(4) Uani d . 1 . .
F F2 0.75847(13) 1.28200(9) 0.87505(16) 0.0449(3) Uani d . 1 . .
F F3 0.58975(12) 1.20628(11) 0.8139(2) 0.0551(4) Uani d . 1 . .
F F4 0.69058(14) 0.77016(10) 0.86879(18) 0.0525(4) Uani d . 1 . .
F F5 0.71980(16) 0.87281(11) 1.05802(17) 0.0663(5) Uani d . 1 . .
F F6 0.54674(13) 0.80495(10) 0.96076(16) 0.0478(3) Uani d . 1 . .
O O1 0.90194(11) 1.10259(10) 0.91208(15) 0.0280(3) Uani d . 1 . .
O O2 0.74816(13) 1.08338(10) 1.04986(15) 0.0293(3) Uani d . 1 . .
O O3 0.54372(11) 0.89593(10) 0.64061(14) 0.0254(3) Uani d . 1 . .
O O4 0.52094(12) 1.00882(11) 0.84680(16) 0.0308(3) Uani d . 1 . .
N N1 0.72049(12) 0.99798(10) 0.79108(15) 0.0167(3) Uani d . 1 . .
C C1 0.89885(15) 0.90047(12) 0.4795(2) 0.0192(3) Uani d . 1 . .
C C2 0.79853(15) 0.96166(12) 0.42518(19) 0.0201(3) Uani d . 1 . .
H H2 0.7706 0.9812 0.3192 0.024 Uiso calc R 1 . .
C C3 0.73954(14) 0.99385(12) 0.52852(18) 0.0182(3) Uani d . 1 . .
H H3 0.6704 1.0358 0.4943 0.022 Uiso calc R 1 . .
C C4 0.78292(14) 0.96396(12) 0.68241(18) 0.0162(3) Uani d . 1 . .
C C5 0.88287(15) 0.90243(12) 0.73621(19) 0.0198(3) Uani d . 1 . .
H H5 0.9106 0.8824 0.8420 0.024 Uiso calc R 1 . .
C C6 0.94185(15) 0.87055(12) 0.6327(2) 0.0218(3) Uani d . 1 . .
H H6 1.0110 0.8286 0.6668 0.026 Uiso calc R 1 . .
C C7 0.70024(18) 1.20199(13) 0.8072(2) 0.0258(4) Uani d . 1 . .
C C8 0.64203(18) 0.84073(14) 0.9298(2) 0.0301(4) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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'
Cl Cl 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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
_geom_angle_publ_flag
O2 S1 O1 . . 123.00(9) ?
O2 S1 N1 . . 110.21(8) ?
O1 S1 N1 . . 106.70(7) ?
O2 S1 C7 . . 106.88(8) ?
O1 S1 C7 . . 105.19(9) ?
N1 S1 C7 . . 103.02(8) ?
O4 S2 O3 . . 122.60(8) ?
O4 S2 N1 . . 109.14(8) ?
O3 S2 N1 . . 107.18(7) ?
O4 S2 C8 . . 107.55(9) ?
O3 S2 C8 . . 105.91(8) ?
N1 S2 C8 . . 102.67(8) ?
C4 N1 S2 . . 118.56(10) ?
C4 N1 S1 . . 118.91(10) ?
S2 N1 S1 . . 122.53(8) ?
C6 C1 C2 . . 122.17(15) ?
C6 C1 Cl1 . . 119.27(13) ?
C2 C1 Cl1 . . 118.56(13) ?
C1 C2 C3 . . 118.74(15) ?
C1 C2 H2 . . 120.6 ?
C3 C2 H2 . . 120.6 ?
C4 C3 C2 . . 119.07(15) ?
C4 C3 H3 . . 120.5 ?
C2 C3 H3 . . 120.5 ?
C5 C4 C3 . . 122.06(15) ?
C5 C4 N1 . . 119.00(14) ?
C3 C4 N1 . . 118.94(14) ?
C4 C5 C6 . . 118.75(15) ?
C4 C5 H5 . . 120.6 ?
C6 C5 H5 . . 120.6 ?
C1 C6 C5 . . 119.21(15) ?
C1 C6 H6 . . 120.4 ?
C5 C6 H6 . . 120.4 ?
F3 C7 F1 . . 110.51(18) ?
F3 C7 F2 . . 108.18(16) ?
F1 C7 F2 . . 109.00(16) ?
F3 C7 S1 . . 110.98(13) ?
F1 C7 S1 . . 110.08(12) ?
F2 C7 S1 . . 108.03(13) ?
F5 C8 F4 . . 110.23(19) ?
F5 C8 F6 . . 109.09(18) ?
F4 C8 F6 . . 108.97(16) ?
F5 C8 S2 . . 111.24(13) ?
F4 C8 S2 . . 109.37(13) ?
F6 C8 S2 . . 107.89(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 . 1.7380(16) ?
S1 O2 . 1.4131(13) ?
S1 O1 . 1.4160(13) ?
S1 N1 . 1.6769(13) ?
S1 C7 . 1.8470(18) ?
S2 O4 . 1.4135(13) ?
S2 O3 . 1.4168(13) ?
S2 N1 . 1.6749(14) ?
S2 C8 . 1.8483(19) ?
F1 C7 . 1.306(2) ?
F2 C7 . 1.317(2) ?
F3 C7 . 1.303(2) ?
F4 C8 . 1.309(3) ?
F5 C8 . 1.304(2) ?
F6 C8 . 1.313(2) ?
N1 C4 . 1.4637(19) ?
C1 C6 . 1.381(2) ?
C1 C2 . 1.385(2) ?
C2 C3 . 1.388(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.387(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.384(2) ?
C5 C6 . 1.388(2) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C3 H3 O3 3_676 0.95 2.57 3.496(2) 164
C5 H5 O1 3_777 0.95 2.59 3.385(2) 141
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O4 S2 N1 C4 . . . . -155.34(12) ?
O3 S2 N1 C4 . . . . -20.57(14) ?
C8 S2 N1 C4 . . . . 90.75(13) ?
O4 S2 N1 S1 . . . . 23.61(12) ?
O3 S2 N1 S1 . . . . 158.38(9) ?
C8 S2 N1 S1 . . . . -90.29(11) ?
O2 S1 N1 C4 . . . . -151.50(12) ?
O1 S1 N1 C4 . . . . -15.75(14) ?
C7 S1 N1 C4 . . . . 94.75(13) ?
O2 S1 N1 S2 . . . . 29.55(12) ?
O1 S1 N1 S2 . . . . 165.30(9) ?
C7 S1 N1 S2 . . . . -84.20(11) ?
C6 C1 C2 C3 . . . . 0.0(2) ?
Cl1 C1 C2 C3 . . . . -179.66(12) ?
C1 C2 C3 C4 . . . . 0.1(2) ?
C2 C3 C4 C5 . . . . -0.4(2) ?
C2 C3 C4 N1 . . . . -179.97(14) ?
S2 N1 C4 C5 . . . . -102.12(15) ?
S1 N1 C4 C5 . . . . 78.89(17) ?
S2 N1 C4 C3 . . . . 77.44(17) ?
S1 N1 C4 C3 . . . . -101.55(15) ?
C3 C4 C5 C6 . . . . 0.6(2) ?
N1 C4 C5 C6 . . . . -179.88(14) ?
C2 C1 C6 C5 . . . . 0.1(3) ?
Cl1 C1 C6 C5 . . . . 179.81(13) ?
C4 C5 C6 C1 . . . . -0.4(2) ?
O2 S1 C7 F3 . . . . -40.94(16) ?
O1 S1 C7 F3 . . . . -173.17(14) ?
N1 S1 C7 F3 . . . . 75.21(15) ?
O2 S1 C7 F1 . . . . -163.59(14) ?
O1 S1 C7 F1 . . . . 64.17(16) ?
N1 S1 C7 F1 . . . . -47.44(16) ?
O2 S1 C7 F2 . . . . 77.50(14) ?
O1 S1 C7 F2 . . . . -54.73(14) ?
N1 S1 C7 F2 . . . . -166.35(12) ?
O4 S2 C8 F5 . . . . -67.64(18) ?
O3 S2 C8 F5 . . . . 159.68(16) ?
N1 S2 C8 F5 . . . . 47.42(18) ?
O4 S2 C8 F4 . . . . 170.36(13) ?
O3 S2 C8 F4 . . . . 37.69(16) ?
N1 S2 C8 F4 . . . . -74.58(15) ?
O4 S2 C8 F6 . . . . 51.97(16) ?
O3 S2 C8 F6 . . . . -80.71(15) ?
N1 S2 C8 F6 . . . . 167.02(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 19013849
