#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/87/2238793.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_2238793
loop_
_publ_author_name
'Sreenivasa, Swamy'
'Palakshamurthy, Bandrehalli Siddagangaiah'
'Tonannavar, Jagdish'
'Jayashree, Yenagi'
'Sudha, Achar Gurumurthy'
'Suchetan, Parameshwar Adimoole'
_publ_section_title
;
 4-Methoxy-N-[(4-methylphenyl)sulfonyl]benzamide including an
 unknown solvate
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1664
_journal_page_last               o1665
_journal_paper_doi               10.1107/S1600536813028158
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C15 H15 N O4 S'
_chemical_formula_moiety         'C15 H15 N O4 S'
_chemical_formula_sum            'C15 H15 N O4 S'
_chemical_formula_weight         305.34
_chemical_name_systematic
;
4-Methoxy-N-[(4-methylphenyl)sulfonyl]benzamide
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                120.00
_cell_formula_units_Z            18
_cell_length_a                   27.1686(16)
_cell_length_b                   27.1686(16)
_cell_length_c                   10.8594(6)
_cell_measurement_reflns_used    1123
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.9
_cell_measurement_theta_min      0.0
_cell_volume                     6941.8(7)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7701
_diffrn_reflns_theta_full        22.86
_diffrn_reflns_theta_max         22.86
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2880
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.19
_platon_squeeze_details
;
;
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.307
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2106
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0393
_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)+(0.0500P)²+5.9239P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1089
_reflns_number_gt                1604
_reflns_number_total             2106
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2649.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               2238793
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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 0.64344(3) 0.92841(3) 0.07169(6) 0.0512(3) Uani d . 1 1
O O2 0.67632(8) 0.92727(8) 0.17255(17) 0.0630(6) Uani d . 1 1
O O3 0.58608(8) 0.93575(8) 0.29224(17) 0.0589(6) Uani d . 1 1
C C9 0.57569(10) 1.01361(10) 0.2290(2) 0.0408(6) Uani d . 1 1
N N1 0.61811(10) 0.97065(10) 0.1035(2) 0.0485(6) Uani d D 1 1
H H1N 0.6281(12) 0.9968(9) 0.055(2) 0.062(10) Uiso d D 1 1
O O1 0.66938(8) 0.94701(8) -0.04522(17) 0.0632(6) Uani d . 1 1
O O4 0.52572(9) 1.13258(9) 0.2828(2) 0.0741(7) Uani d . 1 1
C C8 0.59338(10) 0.97057(11) 0.2137(2) 0.0432(7) Uani d . 1 1
C C10 0.57316(11) 1.04599(11) 0.1330(2) 0.0492(7) Uani d . 1 1
H H10 0.5831 1.0413 0.0538 0.059 Uiso calc R 1 1
C C12 0.54143(11) 1.09243(11) 0.2710(3) 0.0504(7) Uani d . 1 1
C C14 0.56081(11) 1.02166(11) 0.3456(2) 0.0506(7) Uani d . 1 1
H H14 0.5625 1.0004 0.4107 0.061 Uiso calc R 1 1
C C11 0.55601(12) 1.08497(12) 0.1542(3) 0.0555(8) Uani d . 1 1
H H11 0.5543 1.1064 0.0893 0.067 Uiso calc R 1 1
C C13 0.54340(11) 1.06075(12) 0.3676(3) 0.0543(8) Uani d . 1 1
H H13 0.5332 1.0655 0.4465 0.065 Uiso calc R 1 1
C C1 0.58283(12) 0.86088(12) 0.0570(2) 0.0506(7) Uani d . 1 1
C C3 0.53039(16) 0.76272(14) 0.1127(3) 0.0733(9) Uani d . 1 1
H H3 0.5270 0.7326 0.1598 0.088 Uiso calc R 1 1
C C6 0.54185(13) 0.85199(13) -0.0290(3) 0.0591(8) Uani d . 1 1
H H6 0.5458 0.8817 -0.0784 0.071 Uiso calc R 1 1
C C2 0.57735(14) 0.81618(14) 0.1276(3) 0.0640(9) Uani d . 1 1
H H2 0.6052 0.8220 0.1850 0.077 Uiso calc R 1 1
C C5 0.49512(14) 0.79869(14) -0.0406(3) 0.0689(9) Uani d . 1 1
H H5 0.4670 0.7929 -0.0972 0.083 Uiso calc R 1 1
C C4 0.48878(14) 0.75366(14) 0.0291(3) 0.0678(9) Uani d . 1 1
C C15 0.50425(16) 1.13869(16) 0.3982(3) 0.0871(11) Uani d . 1 1
H H15A 0.4715 1.1032 0.4206 0.131 Uiso calc R 1 1
H H15B 0.4938 1.1675 0.3915 0.131 Uiso calc R 1 1
H H15C 0.5330 1.1495 0.4602 0.131 Uiso calc R 1 1
C C7 0.43705(17) 0.69489(15) 0.0145(4) 0.1057(14) Uani d . 1 1
H H7A 0.4150 0.6948 -0.0546 0.159 Uiso calc PR 0.50 1
H H7B 0.4143 0.6851 0.0878 0.159 Uiso calc PR 0.50 1
H H7C 0.4491 0.6676 0.0011 0.159 Uiso calc PR 0.50 1
H H7D 0.4373 0.6702 0.0775 0.159 Uiso calc PR 0.50 1
H H7E 0.4380 0.6799 -0.0649 0.159 Uiso calc PR 0.50 1
H H7F 0.4031 0.6974 0.0218 0.159 Uiso calc PR 0.50 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 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'
S S 0.1246 0.1234 '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 119.45(13)
O1 S1 N1 104.29(12)
O2 S1 N1 109.86(11)
O1 S1 C1 109.32(12)
O2 S1 C1 108.53(13)
N1 S1 C1 104.33(13)
C14 C9 C10 118.5(2)
C14 C9 C8 117.7(2)
C10 C9 C8 123.8(2)
C8 N1 S1 123.9(2)
C8 N1 H1N 121(2)
S1 N1 H1N 113(2)
C12 O4 C15 119.1(2)
O3 C8 N1 120.2(2)
O3 C8 C9 123.1(2)
N1 C8 C9 116.7(2)
C11 C10 C9 120.5(3)
C11 C10 H10 119.8
C9 C10 H10 119.8
O4 C12 C11 115.7(3)
O4 C12 C13 123.8(3)
C11 C12 C13 120.5(2)
C9 C14 C13 121.4(3)
C9 C14 H14 119.3
C13 C14 H14 119.3
C10 C11 C12 120.2(3)
C10 C11 H11 119.9
C12 C11 H11 119.9
C12 C13 C14 119.0(3)
C12 C13 H13 120.5
C14 C13 H13 120.5
C6 C1 C2 120.0(3)
C6 C1 S1 119.9(2)
C2 C1 S1 120.1(2)
C4 C3 C2 120.7(3)
C4 C3 H3 119.7
C2 C3 H3 119.7
C5 C6 C1 119.1(3)
C5 C6 H6 120.4
C1 C6 H6 120.4
C1 C2 C3 119.8(3)
C1 C2 H2 120.1
C3 C2 H2 120.1
C6 C5 C4 121.7(3)
C6 C5 H5 119.1
C4 C5 H5 119.1
C3 C4 C5 118.6(3)
C3 C4 C7 120.2(3)
C5 C4 C7 121.1(3)
O4 C15 H15A 109.5
O4 C15 H15B 109.5
H15A C15 H15B 109.5
O4 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C4 C7 H7D 109.5
H7A C7 H7D 141.1
H7B C7 H7D 56.3
H7C C7 H7D 56.3
C4 C7 H7E 109.5
H7A C7 H7E 56.3
H7B C7 H7E 141.1
H7C C7 H7E 56.3
H7D C7 H7E 109.5
C4 C7 H7F 109.5
H7A C7 H7F 56.3
H7B C7 H7F 56.3
H7C C7 H7F 141.1
H7D C7 H7F 109.5
H7E C7 H7F 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4169(19)
S1 O2 1.4235(19)
S1 N1 1.643(2)
S1 C1 1.756(3)
O3 C8 1.214(3)
C9 C14 1.380(3)
C9 C10 1.388(3)
C9 C8 1.479(4)
N1 C8 1.372(3)
N1 H1N 0.817(17)
O4 C12 1.362(3)
O4 C15 1.427(4)
C10 C11 1.373(4)
C10 H10 0.9300
C12 C11 1.374(4)
C12 C13 1.375(4)
C14 C13 1.382(4)
C14 H14 0.9300
C11 H11 0.9300
C13 H13 0.9300
C1 C6 1.379(4)
C1 C2 1.380(4)
C3 C4 1.373(4)
C3 C2 1.382(4)
C3 H3 0.9300
C6 C5 1.373(4)
C6 H6 0.9300
C2 H2 0.9300
C5 C4 1.374(4)
C5 H5 0.9300
C4 C7 1.519(5)
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C7 H7D 0.9600
C7 H7E 0.9600
C7 H7F 0.9600
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 H1N O3 9_564 0.817(17) 2.257(19) 3.038(3) 160(3)
N1 H1N O2 9_564 0.817(17) 2.59(3) 3.140(3) 126(2)
C10 H10 O3 9_564 0.93 2.58 3.249(3) 129
C15 H15A O1 15 0.96 2.56 3.454(4) 154
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 C8 -174.5(2)
O2 S1 N1 C8 -45.3(3)
C1 S1 N1 C8 70.9(2)
S1 N1 C8 O3 -4.4(4)
S1 N1 C8 C9 176.81(18)
C14 C9 C8 O3 13.2(4)
C10 C9 C8 O3 -166.6(3)
C14 C9 C8 N1 -168.0(2)
C10 C9 C8 N1 12.1(4)
C14 C9 C10 C11 -0.2(4)
C8 C9 C10 C11 179.7(2)
C15 O4 C12 C11 173.4(3)
C15 O4 C12 C13 -6.9(4)
C10 C9 C14 C13 0.3(4)
C8 C9 C14 C13 -179.5(2)
C9 C10 C11 C12 0.3(4)
O4 C12 C11 C10 179.2(2)
C13 C12 C11 C10 -0.5(4)
O4 C12 C13 C14 -179.0(2)
C11 C12 C13 C14 0.6(4)
C9 C14 C13 C12 -0.5(4)
O1 S1 C1 C6 -52.8(2)
O2 S1 C1 C6 175.4(2)
N1 S1 C1 C6 58.3(2)
O1 S1 C1 C2 124.4(2)
O2 S1 C1 C2 -7.4(3)
N1 S1 C1 C2 -124.5(2)
C2 C1 C6 C5 1.8(4)
S1 C1 C6 C5 179.0(2)
C6 C1 C2 C3 -0.7(4)
S1 C1 C2 C3 -177.9(2)
C4 C3 C2 C1 -0.6(5)
C1 C6 C5 C4 -1.6(5)
C2 C3 C4 C5 0.8(5)
C2 C3 C4 C7 -179.3(3)
C6 C5 C4 C3 0.3(5)
C6 C5 C4 C7 -179.6(3)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.000 181 22 ' '
2 0.000 0.000 0.500 9 1 ' '
3 0.333 0.667 0.667 181 22 ' '
4 0.333 0.667 0.167 8 1 ' '
5 0.667 0.333 0.333 181 22 ' '
6 0.667 0.333 0.833 8 1 ' '
