#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/73/2207321.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_2207321
loop_
_publ_author_name
'Kimura, Masaharu'
'Hourai, Shinji'
_publ_section_title
;
 Methyl 5-chloro-2-{[(trifluoromethyl)sulfonyl]amino}benzoate
;
_journal_coeditor_code           OB6590
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3944
_journal_page_last               o3945
_journal_paper_doi               10.1107/S1600536805034902
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C9 H7 Cl F3 N O4 S'
_chemical_formula_moiety         'C9 H7 Cl F3 N O4 S'
_chemical_formula_sum            'C9 H7 Cl F3 N O4 S'
_chemical_formula_weight         317.67
_chemical_melting_point          356
_chemical_name_systematic
;
Methyl 5-chloro-2-(trifluoromethylsulfonamido)benzoate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                85.212(9)
_cell_angle_beta                 85.470(10)
_cell_angle_gamma                88.939(6)
_cell_formula_units_Z            2
_cell_length_a                   5.341(2)
_cell_length_b                   9.8870(10)
_cell_length_c                   11.754(3)
_cell_measurement_reflns_used    3856
_cell_measurement_temperature    296.1
_cell_measurement_theta_max      66.8
_cell_measurement_theta_min      3.8
_cell_volume                     616.5(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction
'CrystalStructure (Rigaku/MSC & Rigaku, 2004)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  CrystalStructure
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9136
_diffrn_measured_fraction_theta_max 0.9136
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.127
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12598
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_exptl_absorpt_coefficient_mu    4.837
_exptl_absorpt_correction_T_max  0.616
_exptl_absorpt_correction_T_min  0.178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             320.00
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2073
_refine_ls_R_factor_gt           0.1050
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1063P)²+1.5441P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2840
_reflns_number_gt                1398
_reflns_number_total             2073
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            ob6590.cif
_cod_data_source_block           I
_cod_database_code               2207321
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
loop_
_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_type_symbol
Cl1 0.8261(5) 0.3175(2) 0.6298(2) 0.0859(8) Uani d . 1.00 Cl
S1 0.0020(4) 0.1370(2) 0.2240(2) 0.0705(7) Uani d . 1.00 S
F1 0.3230(10) 0.1003(6) 0.0536(4) 0.099(2) Uani d . 1.00 F
F2 0.1110(10) -0.0741(5) 0.1131(5) 0.108(2) Uani d . 1.00 F
F3 0.4070(10) -0.0144(5) 0.2087(4) 0.094(2) Uani d . 1.00 F
O1 0.3930(10) 0.4687(5) 0.1514(5) 0.077(2) Uani d . 1.00 O
O2 0.7400(10) 0.5343(6) 0.2210(5) 0.092(2) Uani d . 1.00 O
O3 -0.0860(10) 0.0537(6) 0.3218(5) 0.089(2) Uani d . 1.00 O
O4 -0.1590(10) 0.1923(6) 0.1418(5) 0.084(2) Uani d . 1.00 O
N1 0.1660(10) 0.2577(7) 0.2573(6) 0.072(2) Uani d . 1.00 N
C1 0.639(2) 0.2953(8) 0.5191(6) 0.066(2) Uani d . 1.00 C
C2 0.460(2) 0.1950(8) 0.5315(7) 0.071(2) Uani d . 1.00 C
C3 0.307(2) 0.1806(8) 0.4457(7) 0.073(2) Uani d . 1.00 C
C4 0.3290(10) 0.2644(7) 0.3467(6) 0.060(2) Uani d . 1.00 C
C5 0.5110(10) 0.3670(7) 0.3317(6) 0.058(2) Uani d . 1.00 C
C6 0.663(2) 0.3799(7) 0.4203(6) 0.065(2) Uani d . 1.00 C
C7 0.539(2) 0.4598(7) 0.2265(6) 0.063(2) Uani d . 1.00 C
C8 0.781(2) 0.6310(10) 0.1217(9) 0.125(4) Uani d . 1.00 C
C9 0.227(2) 0.0309(8) 0.1457(7) 0.074(2) Uani d . 1.00 C
H1 0.4429 0.1362 0.5998 0.085 Uiso c R 1.00 H
H2 0.1837 0.1116 0.4547 0.088 Uiso c R 1.00 H
H3 0.7862 0.4488 0.4125 0.078 Uiso c R 1.00 H
H4 0.7968 0.5828 0.0536 0.150 Uiso c R 1.00 H
H5 0.9301 0.6795 0.1273 0.150 Uiso c R 1.00 H
H6 0.6408 0.6927 0.1183 0.150 Uiso c R 1.00 H
H7 0.18(2) 0.304(9) 0.200(7) 0.08(3) Uiso d . 1.00 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Cl Cl 0.364 0.702
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.073 0.053
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.031 0.018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.049 0.032
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.333 0.557
;
International Tables for Crystallography
(1992, 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
_geom_angle_publ_flag
Cl1 C1 C2 120.1(6) ?
Cl1 C1 C6 120.2(6) ?
O4 S1 O3 122.6(4) yes
N1 S1 O3 111.3(4) ?
C9 S1 O3 104.9(4) ?
N1 S1 O4 107.1(4) ?
C9 S1 O4 105.1(4) ?
C9 S1 N1 104.1(4) yes
S1 N1 C4 131.0(6) yes
S1 C9 F1 109.6(6) ?
S1 C9 F2 109.5(6) ?
S1 C9 F3 111.7(6) ?
F1 C9 F2 107.7(7) ?
F1 C9 F3 109.8(7) ?
F2 C9 F3 108.4(7) ?
O1 C7 O2 122.2(6) ?
O1 C7 C5 125.0(7) ?
O2 C7 C5 112.8(7) ?
C8 O2 C7 116.8(7) ?
N1 C4 C5 116.8(6) ?
N1 C4 C3 122.7(7) ?
C1 C2 C3 120.0(7) ?
C6 C1 C2 119.7(7) ?
C1 C6 C5 121.4(7) ?
C2 C3 C4 120.7(8) ?
C3 C4 C5 120.4(7) ?
C4 C5 C7 121.9(7) ?
C4 C5 C6 117.7(6) ?
C7 C5 C6 120.4(6) ?
S1 N1 H7 102(6) ?
O2 C8 H4 109.4691 ?
O2 C8 H5 109.4700 ?
O2 C8 H6 109.4653 ?
H7 N1 C4 121(6) ?
C1 C2 H1 119.9872 ?
C1 C6 H3 119.2864 ?
C2 C3 H2 119.6463 ?
H1 C2 C3 119.9873 ?
H2 C3 C4 119.6466 ?
C5 C6 H3 119.2867 ?
H5 C8 H4 109.4732 ?
H6 C8 H4 109.4777 ?
H6 C8 H5 109.4721 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 1.731(8) ?
S1 O3 1.411(6) ?
S1 O4 1.412(6) ?
S1 N1 1.586(8) yes
S1 C9 1.826(9) ?
F1 C9 1.306(9) ?
F2 C9 1.320(10) ?
F3 C9 1.310(10) ?
O1 C7 1.220(10) ?
O2 C7 1.310(10) ?
O2 C8 1.450(10) ?
N1 C4 1.420(10) yes
C1 C2 1.380(10) ?
C1 C6 1.370(10) ?
C2 C3 1.370(10) ?
C3 C4 1.370(10) ?
C4 C5 1.410(10) ?
C5 C6 1.390(10) ?
C5 C7 1.476(9) ?
C9 S1 1.826(9) ?
N1 H7 0.78(8) ?
C2 H1 0.9500 ?
C3 H2 0.9500 ?
C6 H3 0.9500 ?
C8 H4 0.9500 ?
C8 H5 0.9500 ?
C8 H6 0.9500 ?
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_publ_flag
N1 H7 O1 0.78(8) 2.01(8) 2.606(9) 132(8) yes
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
_geom_torsion_publ_flag
O3 S1 N1 C4 33.1(8) ?
O4 S1 N1 C4 169.7(7) ?
C9 S1 N1 C4 -79.3(7) yes
O3 S1 C9 F1 -179.0(5) ?
O3 S1 C9 F2 63.0(6) ?
O3 S1 C9 F3 -57.2(6) ?
O4 S1 C9 F1 50.5(7) ?
O4 S1 C9 F2 -67.5(6) ?
O4 S1 C9 F3 172.3(5) ?
N1 S1 C9 F1 -62.0(6) ?
N1 S1 C9 F2 -180.0(4) ?
N1 S1 C9 F3 59.9(6) ?
C8 O2 C7 O1 .0(10) ?
C8 O2 C7 C5 -178.9(6) ?
S1 N1 C4 C3 -24.0(10) ?
S1 N1 C4 C5 158.8(7) yes
Cl1 C1 C2 C3 177.8(7) ?
C6 C1 C2 C3 .0(10) ?
Cl1 C1 C6 C5 -178.1(6) ?
C2 C1 C6 C5 -0.3(9) ?
C1 C2 C3 C4 .0(10) ?
C2 C3 C4 N1 -176.7(7) ?
C2 C3 C4 C5 .0(10) ?
N1 C4 C5 C6 176.6(7) ?
N1 C4 C5 C7 -2.0(10) ?
C3 C4 C5 C6 .0(10) ?
C3 C4 C5 C7 -179.5(7) ?
C4 C5 C6 C1 .0(10) ?
C7 C5 C6 C1 179.6(7) ?
C4 C5 C7 O1 9.0(10) yes
C4 C5 C7 O2 -170.4(7) ?
C6 C5 C7 O1 -169.3(7) ?
C6 C5 C7 O2 10.0(10) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8037476
