#------------------------------------------------------------------------------
#$Date: 2015-10-29 05:38:15 +0200 (Thu, 29 Oct 2015) $
#$Revision: 169808 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/12/2241213.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_2241213
loop_
_publ_author_name
'Rodrigues, Vinola Z.'
'Preema, C. P.'
'Naveen, S.'
'Lokanath, N. K.'
'Suchetan, P. A.'
_publ_section_title
;
 Crystal structures of
 4-methoxy-N-(4-methylphenyl)benzenesulfonamide and
 N-(4-fluorophenyl)-4-methoxybenzenesulfonamide
;
_journal_coeditor_code           CV5497
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1388
_journal_page_last               1391
_journal_paper_doi               10.1107/S2056989015019787
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C13 H12 F N O3 S'
_chemical_formula_moiety         'C13 H12 F N O3 S'
_chemical_formula_sum            'C13 H12 F N O3 S'
_chemical_formula_weight         281.30
_chemical_name_systematic
;
N-(4-Fluorophenyl)-4-methoxybenzenesulfonamide
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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            4
_cell_length_a                   20.2188(13)
_cell_length_b                   12.1199(8)
_cell_length_c                   5.1770(3)
_cell_measurement_reflns_used    143
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      64.1
_cell_measurement_theta_min      4.3
_cell_volume                     1268.62(14)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5438
_diffrn_reflns_theta_full        64.05
_diffrn_reflns_theta_max         64.05
_diffrn_reflns_theta_min         4.25
_diffrn_standards_decay_%        0.1
_diffrn_standards_interval_count 1
_diffrn_standards_interval_time  0.5
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    2.437
_exptl_absorpt_correction_T_max  0.585
_exptl_absorpt_correction_T_min  0.481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.347
_refine_ls_abs_structure_details
;
Flack (1983), 973 Friedel pairs
;
_refine_ls_abs_structure_Flack   0.08(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         1830
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0337
_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)+(0.0719P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1002
_reflns_number_gt                1784
_reflns_number_total             1830
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv5497sup1.cif
_cod_data_source_block           II
_cod_database_code               2241213
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'
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 0.77164(2) 0.42206(4) 0.40154(13) 0.0172(2) Uani d . 1 1
F F1 0.96703(8) -0.00461(12) 0.4446(3) 0.0328(4) Uani d . 1 1
O O1 0.75213(8) 0.53031(14) 0.4790(4) 0.0229(4) Uani d . 1 1
O O2 0.79392(9) 0.40209(15) 0.1426(4) 0.0234(4) Uani d . 1 1
O O3 0.56267(8) 0.10112(16) 0.6458(4) 0.0289(5) Uani d . 1 1
N N1 0.83314(9) 0.38833(18) 0.5945(4) 0.0179(5) Uani d D 1 1
C C10 0.93385(12) 0.0915(2) 0.4822(6) 0.0245(6) Uani d . 1 1
C C6 0.70105(11) 0.2317(2) 0.3318(5) 0.0224(6) Uani d . 1 1
H H6 0.7303 0.2162 0.1979 0.027 Uiso calc R 1 1
C C8 0.85326(11) 0.1947(2) 0.7108(5) 0.0229(6) Uani d . 1 1
H H8 0.8215 0.2003 0.8401 0.028 Uiso calc R 1 1
C C7 0.86643(11) 0.2844(2) 0.5534(5) 0.0181(5) Uani d . 1 1
C C4 0.60893(10) 0.1812(2) 0.5970(6) 0.0216(6) Uani d . 1 1
C C2 0.66316(11) 0.3540(2) 0.6686(6) 0.0221(5) Uani d . 1 1
H H2 0.6672 0.4199 0.7591 0.027 Uiso calc R 1 1
C C5 0.65224(10) 0.15819(19) 0.3967(6) 0.0234(5) Uani d . 1 1
H H5 0.6482 0.0924 0.3056 0.028 Uiso calc R 1 1
C C11 0.94793(12) 0.1792(2) 0.3219(6) 0.0277(6) Uani d . 1 1
H H11 0.9794 0.1731 0.1917 0.033 Uiso calc R 1 1
C C12 0.91355(11) 0.2773(2) 0.3611(5) 0.0240(6) Uani d . 1 1
H H12 0.9224 0.3382 0.2575 0.029 Uiso calc R 1 1
C C3 0.61372(11) 0.2795(2) 0.7337(5) 0.0234(6) Uani d . 1 1
H H3 0.5843 0.2952 0.8667 0.028 Uiso calc R 1 1
C C1 0.70619(12) 0.3303(2) 0.4696(5) 0.0186(5) Uani d . 1 1
C C13 0.51905(13) 0.1183(2) 0.8577(6) 0.0330(7) Uani d . 1 1
H H13A 0.5443 0.1268 1.0134 0.049 Uiso calc R 1 1
H H13B 0.4901 0.0560 0.8745 0.049 Uiso calc R 1 1
H H13C 0.4933 0.1837 0.8281 0.049 Uiso calc R 1 1
C C9 0.88759(13) 0.0962(2) 0.6755(6) 0.0261(6) Uani d . 1 1
H H9 0.8794 0.0353 0.7801 0.031 Uiso calc R 1 1
H H1 0.8245(14) 0.399(2) 0.763(2) 0.023(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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 S1 O2 120.28(11)
O1 S1 N1 105.44(11)
O2 S1 N1 106.74(11)
O1 S1 C1 108.44(11)
O2 S1 C1 108.41(11)
N1 S1 C1 106.77(11)
C4 O3 C13 117.5(2)
C7 N1 S1 118.62(16)
C7 N1 H1 111.3(19)
S1 N1 H1 113.8(19)
F1 C10 C9 118.5(2)
F1 C10 C11 118.3(2)
C9 C10 C11 123.3(2)
C5 C6 C1 119.0(2)
C5 C6 H6 120.5
C1 C6 H6 120.5
C7 C8 C9 120.0(2)
C7 C8 H8 120.0
C9 C8 H8 120.0
C12 C7 C8 120.5(2)
C12 C7 N1 118.9(2)
C8 C7 N1 120.5(2)
O3 C4 C5 115.2(2)
O3 C4 C3 124.1(2)
C5 C4 C3 120.7(2)
C1 C2 C3 120.0(2)
C1 C2 H2 120.0
C3 C2 H2 120.0
C6 C5 C4 120.5(2)
C6 C5 H5 119.8
C4 C5 H5 119.8
C10 C11 C12 117.9(2)
C10 C11 H11 121.1
C12 C11 H11 121.1
C7 C12 C11 120.2(2)
C7 C12 H12 119.9
C11 C12 H12 119.9
C2 C3 C4 118.9(2)
C2 C3 H3 120.5
C4 C3 H3 120.5
C2 C1 C6 120.9(2)
C2 C1 S1 119.40(19)
C6 C1 S1 119.56(19)
O3 C13 H13A 109.5
O3 C13 H13B 109.5
H13A C13 H13B 109.5
O3 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C10 C9 C8 118.1(3)
C10 C9 H9 121.0
C8 C9 H9 121.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4275(18)
S1 O2 1.435(2)
S1 N1 1.647(2)
S1 C1 1.764(2)
F1 C10 1.358(3)
O3 C4 1.371(3)
O3 C13 1.423(3)
N1 C7 1.444(3)
N1 H1 0.898(10)
C10 C9 1.371(4)
C10 C11 1.378(4)
C6 C5 1.372(3)
C6 C1 1.395(3)
C6 H6 0.9300
C8 C7 1.385(4)
C8 C9 1.394(4)
C8 H8 0.9300
C7 C12 1.380(3)
C4 C5 1.385(4)
C4 C3 1.390(4)
C2 C1 1.378(4)
C2 C3 1.388(4)
C2 H2 0.9300
C5 H5 0.9300
C11 C12 1.392(4)
C11 H11 0.9300
C12 H12 0.9300
C3 H3 0.9300
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C9 H9 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 O2 1_556 0.899(12) 2.061(13) 2.951(3) 171(3)
C6 H6 O1 4_644 0.93 2.55 3.192(3) 127
C13 H13B O3 2_655 0.96 2.60 3.468(3) 151
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 S1 N1 C7 -176.37(18)
O2 S1 N1 C7 -47.4(2)
C1 S1 N1 C7 68.4(2)
C9 C8 C7 C12 -0.1(4)
C9 C8 C7 N1 -177.5(2)
S1 N1 C7 C12 80.1(3)
S1 N1 C7 C8 -102.5(2)
C13 O3 C4 C5 177.0(2)
C13 O3 C4 C3 -3.0(4)
C1 C6 C5 C4 -0.3(4)
O3 C4 C5 C6 -179.4(2)
C3 C4 C5 C6 0.7(4)
F1 C10 C11 C12 179.8(2)
C9 C10 C11 C12 0.5(4)
C8 C7 C12 C11 0.6(4)
N1 C7 C12 C11 178.0(2)
C10 C11 C12 C7 -0.8(4)
C1 C2 C3 C4 0.5(4)
O3 C4 C3 C2 179.3(2)
C5 C4 C3 C2 -0.8(4)
C3 C2 C1 C6 -0.2(4)
C3 C2 C1 S1 -176.4(2)
C5 C6 C1 C2 0.1(4)
C5 C6 C1 S1 176.26(19)
O1 S1 C1 C2 -27.8(2)
O2 S1 C1 C2 -159.9(2)
N1 S1 C1 C2 85.4(2)
O1 S1 C1 C6 156.0(2)
O2 S1 C1 C6 23.8(2)
N1 S1 C1 C6 -90.8(2)
F1 C10 C9 C8 -179.3(2)
C11 C10 C9 C8 0.0(4)
C7 C8 C9 C10 -0.2(4)

_cod_database_fobs_code 2241213
