#------------------------------------------------------------------------------
#$Date: 2016-04-01 04:44:44 +0300 (Fri, 01 Apr 2016) $
#$Revision: 180671 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/16/2241630.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_2241630
loop_
_publ_author_name
'Suchetan, P. A.'
'Naveen, S.'
'Lokanath, N. K.'
'Srivishnu, K. S.'
'Supriya, G. M.'
'Lakshmikantha, H. N.'
_publ_section_title
;
 Crystal structures of three N-(arylsulfonyl)-4-fluorobenzamides
;
_journal_coeditor_code           SU5287
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              575
_journal_page_last               582
_journal_paper_doi               10.1107/S2056989016005089
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C13 H9 Cl F N O3 S, H2 O'
_chemical_formula_moiety         'C13 H9 Cl F N O3 S, H2 O'
_chemical_formula_sum            'C13 H11 Cl F N O4 S'
_chemical_formula_weight         331.74
_chemical_melting_point          456
_chemical_name_systematic
;
N-(4-Chlorophenylsulfonyl)-4-fluorobenzamide monohydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                90.00
_cell_angle_beta                 94.4810(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   45.5989(11)
_cell_length_b                   4.88530(10)
_cell_length_c                   12.6517(3)
_cell_measurement_reflns_used    163
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      64.3
_cell_measurement_theta_min      5.8
_cell_volume                     2809.73(11)
_computing_cell_refinement
;
APEX2 and SAINT-Plus (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT-Plus and XPREP (Bruker, 2009)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11176
_diffrn_reflns_theta_full        64.31
_diffrn_reflns_theta_max         64.31
_diffrn_reflns_theta_min         5.84
_diffrn_standards_decay_%        0.1
_diffrn_standards_interval_count 1
_diffrn_standards_interval_time  2
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    4.064
_exptl_absorpt_correction_T_max  0.393
_exptl_absorpt_correction_T_min  0.369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.347
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2320
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.935
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0385
_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)+(0.0912P)²+2.0870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1184
_reflns_number_gt                2030
_reflns_number_total             2320
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            su5287sup1.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2241630
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
S S1 0.356285(11) 0.64551(10) 0.55127(4) 0.0147(2) Uani d . 1 1
Cl Cl1 0.261887(12) -0.14924(12) 0.34233(4) 0.0273(2) Uani d . 1 1
O O2 0.36322(3) 0.8548(3) 0.47847(11) 0.0176(4) Uani d . 1 1
O O1 0.34790(3) 0.7192(3) 0.65445(11) 0.0195(4) Uani d . 1 1
F F1 0.49577(3) -0.3420(3) 0.62191(12) 0.0384(4) Uani d . 1 1
O O3 0.39675(3) 0.4091(3) 0.40288(11) 0.0207(4) Uani d . 1 1
O O4 0.38058(4) 0.1618(4) 0.75835(13) 0.0290(4) Uani d GD 1 1
N N1 0.38535(4) 0.4484(4) 0.57495(14) 0.0161(4) Uani d . 1 1
C C7 0.40210(5) 0.3508(4) 0.49595(16) 0.0165(5) Uani d . 1 1
C C8 0.42713(5) 0.1710(4) 0.53341(17) 0.0174(5) Uani d . 1 1
C C3 0.28843(5) 0.1252(5) 0.50950(18) 0.0216(5) Uani d . 1 1
H H3 0.2753 0.0371 0.5507 0.026 Uiso calc R 1 1
C C13 0.43853(5) -0.0018(5) 0.45932(17) 0.0218(5) Uani d . 1 1
H H13 0.4305 -0.0004 0.3895 0.026 Uiso calc R 1 1
C C2 0.30931(5) 0.3027(5) 0.55508(17) 0.0206(5) Uani d . 1 1
H H2 0.3105 0.3346 0.6278 0.025 Uiso calc R 1 1
C C1 0.32848(4) 0.4331(4) 0.49134(16) 0.0155(5) Uani d . 1 1
C C6 0.32692(5) 0.3910(5) 0.38239(16) 0.0174(5) Uani d . 1 1
H H6 0.3397 0.4821 0.3406 0.021 Uiso calc R 1 1
C C5 0.30619(5) 0.2126(5) 0.33712(16) 0.0189(5) Uani d . 1 1
H H5 0.3049 0.1814 0.2644 0.023 Uiso calc R 1 1
C C4 0.28742(5) 0.0806(5) 0.40070(17) 0.0190(5) Uani d . 1 1
C C9 0.43954(5) 0.1702(5) 0.63795(18) 0.0241(5) Uani d . 1 1
H H9 0.4321 0.2858 0.6878 0.029 Uiso calc R 1 1
C C10 0.46276(5) -0.0009(6) 0.66765(19) 0.0295(6) Uani d . 1 1
H H10 0.4712 -0.0013 0.7369 0.035 Uiso calc R 1 1
C C12 0.46171(5) -0.1755(5) 0.48843(19) 0.0265(6) Uani d . 1 1
H H12 0.4694 -0.2917 0.4393 0.032 Uiso calc R 1 1
C C11 0.47306(5) -0.1710(5) 0.5923(2) 0.0264(6) Uani d . 1 1
H H1O4 0.3743(8) 0.011(6) 0.761(3) 0.067(12) Uiso d D 1 1
H H1 0.3854(6) 0.373(6) 0.634(2) 0.037(8) Uiso d . 1 1
H H2O4 0.3812(7) 0.229(6) 0.8178(19) 0.039(8) Uiso d D 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
O2 S1 O1 119.70(9)
O2 S1 N1 108.70(9)
O1 S1 N1 104.43(9)
O2 S1 C1 109.39(9)
O1 S1 C1 107.77(9)
N1 S1 C1 105.99(10)
H1O4 O4 H2O4 109(3)
C7 N1 S1 123.36(15)
C7 N1 H1 122(2)
S1 N1 H1 112(2)
O3 C7 N1 122.4(2)
O3 C7 C8 122.48(19)
N1 C7 C8 115.13(18)
C13 C8 C9 119.4(2)
C13 C8 C7 117.45(19)
C9 C8 C7 123.2(2)
C2 C3 C4 118.7(2)
C2 C3 H3 120.6
C4 C3 H3 120.6
C12 C13 C8 120.7(2)
C12 C13 H13 119.6
C8 C13 H13 119.6
C3 C2 C1 119.4(2)
C3 C2 H2 120.3
C1 C2 H2 120.3
C2 C1 C6 121.5(2)
C2 C1 S1 118.95(16)
C6 C1 S1 119.53(16)
C5 C6 C1 119.1(2)
C5 C6 H6 120.4
C1 C6 H6 120.4
C6 C5 C4 119.3(2)
C6 C5 H5 120.3
C4 C5 H5 120.3
C5 C4 C3 122.0(2)
C5 C4 Cl1 118.63(17)
C3 C4 Cl1 119.37(17)
C10 C9 C8 120.4(2)
C10 C9 H9 119.8
C8 C9 H9 119.8
C9 C10 C11 118.3(2)
C9 C10 H10 120.8
C11 C10 H10 120.8
C11 C12 C13 117.9(2)
C11 C12 H12 121.0
C13 C12 H12 121.0
F1 C11 C12 118.4(2)
F1 C11 C10 118.3(2)
C12 C11 C10 123.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4279(15)
S1 O1 1.4346(14)
S1 N1 1.6466(18)
S1 C1 1.763(2)
Cl1 C4 1.740(2)
F1 C11 1.360(3)
O3 C7 1.217(3)
O4 H1O4 0.79(3)
O4 H2O4 0.82(2)
N1 C7 1.389(3)
N1 H1 0.84(3)
C7 C8 1.488(3)
C8 C13 1.392(3)
C8 C9 1.397(3)
C3 C2 1.380(3)
C3 C4 1.391(3)
C3 H3 0.9300
C13 C12 1.382(3)
C13 H13 0.9300
C2 C1 1.389(3)
C2 H2 0.9300
C1 C6 1.390(3)
C6 C5 1.377(3)
C6 H6 0.9300
C5 C4 1.380(3)
C5 H5 0.9300
C9 C10 1.378(3)
C9 H9 0.9300
C10 C11 1.375(4)
C10 H10 0.9300
C12 C11 1.374(3)
C12 H12 0.9300
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
N1 H1 O4 1_555 0.83(3) 1.91(3) 2.733(3) 171(2)
O4 H1O4 O1 1_545 0.79(3) 2.25(3) 2.884(2) 138(3)
O4 H2O4 O2 6_566 0.82(2) 2.29(3) 2.955(2) 139(3)
O4 H2O4 O3 6_566 0.82(2) 2.16(3) 2.841(2) 141(3)
C5 H5 O1 6_565 0.93 2.54 3.124(3) 121
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
O2 S1 N1 C7 -45.29(19)
O1 S1 N1 C7 -174.12(17)
C1 S1 N1 C7 72.20(19)
S1 N1 C7 O3 1.5(3)
S1 N1 C7 C8 -178.80(14)
O3 C7 C8 C13 -20.8(3)
N1 C7 C8 C13 159.45(19)
O3 C7 C8 C9 158.7(2)
N1 C7 C8 C9 -21.0(3)
C9 C8 C13 C12 0.7(3)
C7 C8 C13 C12 -179.7(2)
C4 C3 C2 C1 0.5(3)
C3 C2 C1 C6 0.7(3)
C3 C2 C1 S1 -176.74(17)
O2 S1 C1 C2 -151.16(17)
O1 S1 C1 C2 -19.5(2)
N1 S1 C1 C2 91.82(19)
O2 S1 C1 C6 31.4(2)
O1 S1 C1 C6 163.03(17)
N1 S1 C1 C6 -85.63(19)
C2 C1 C6 C5 -1.0(3)
S1 C1 C6 C5 176.33(16)
C1 C6 C5 C4 0.2(3)
C6 C5 C4 C3 1.0(3)
C6 C5 C4 Cl1 -178.71(16)
C2 C3 C4 C5 -1.4(3)
C2 C3 C4 Cl1 178.32(18)
C13 C8 C9 C10 -0.3(3)
C7 C8 C9 C10 -179.8(2)
C8 C9 C10 C11 -0.6(4)
C8 C13 C12 C11 -0.2(3)
C13 C12 C11 F1 179.7(2)
C13 C12 C11 C10 -0.8(4)
C9 C10 C11 F1 -179.3(2)
C9 C10 C11 C12 1.2(4)
