#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/92/2219259.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_2219259
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Babitha, K. S.'
'Fuess, Hartmut'
_publ_section_title
;
 N-(2,6-Dimethylphenyl)benzenesulfonamide
;
_journal_coeditor_code           BT2760
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1691
_journal_paper_doi               10.1107/S1600536808024653
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C14 H15 N O2 S'
_chemical_formula_moiety         'C14 H15 N O2 S'
_chemical_formula_sum            'C14 H15 N O2 S'
_chemical_formula_weight         261.33
_chemical_name_systematic
;
N-(2,6-Dimethylphenyl)benzenesulfonamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.681(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.2133(7)
_cell_length_b                   17.971(2)
_cell_length_c                   14.0400(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      19.24
_cell_measurement_theta_min      3.99
_cell_volume                     1314.8(2)
_computing_cell_refinement       'CAD-4/PC (Enraf--Nonius, 1996)'
_computing_data_collection       'CAD-4/PC (Enraf--Nonius, 1996)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1987)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2622
_diffrn_reflns_theta_full        66.94
_diffrn_reflns_theta_max         66.94
_diffrn_reflns_theta_min         4.00
_diffrn_standards_decay_%        1.0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.135
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.415
_refine_ls_extinction_coef       0.0060(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0467
_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)+(0.0807P)²+0.6081P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1342
_reflns_number_gt                2197
_reflns_number_total             2340
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2760.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2219259
_cod_database_fobs_code          2219259
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C C1 -0.0070(4) 0.19125(11) 0.78195(15) 0.0359(5) Uani d . 1
C C2 -0.2175(4) 0.23812(13) 0.7860(2) 0.0518(6) Uani d . 1
H H2 -0.3303 0.2434 0.7339 0.062 Uiso calc R 1
C C3 -0.2557(5) 0.27695(15) 0.8699(3) 0.0677(8) Uani d . 1
H H3 -0.3972 0.3081 0.8744 0.081 Uiso calc R 1
C C4 -0.0875(6) 0.26990(16) 0.9461(2) 0.0666(8) Uani d . 1
H H4 -0.1141 0.2969 1.0014 0.080 Uiso calc R 1
C C5 0.1186(6) 0.22354(15) 0.94146(19) 0.0590(7) Uani d . 1
H H5 0.2309 0.2186 0.9938 0.071 Uiso calc R 1
C C6 0.1608(4) 0.18376(13) 0.85885(17) 0.0453(5) Uani d . 1
H H6 0.3017 0.1522 0.8554 0.054 Uiso calc R 1
C C7 -0.0178(4) 0.00007(11) 0.74093(15) 0.0373(5) Uani d . 1
C C8 -0.1139(4) -0.01229(12) 0.83144(16) 0.0437(5) Uani d . 1
C C9 -0.0176(6) -0.07186(15) 0.8839(2) 0.0609(7) Uani d . 1
H H9 -0.0788 -0.0809 0.9444 0.073 Uiso calc R 1
C C10 0.1675(7) -0.11784(16) 0.8480(3) 0.0730(9) Uani d . 1
H H10 0.2336 -0.1568 0.8848 0.088 Uiso calc R 1
C C11 0.2541(6) -0.10620(14) 0.7582(2) 0.0680(8) Uani d . 1
H H11 0.3769 -0.1382 0.7343 0.082 Uiso calc R 1
C C12 0.1628(5) -0.04751(13) 0.70148(18) 0.0498(6) Uani d . 1
C C13 -0.3213(5) 0.03545(14) 0.87194(18) 0.0521(6) Uani d . 1
H H13A -0.4740 0.0316 0.8323 0.063 Uiso calc R 1
H H13B -0.2651 0.0863 0.8741 0.063 Uiso calc R 1
H H13C -0.3570 0.0189 0.9352 0.063 Uiso calc R 1
C C14 0.2511(6) -0.03980(16) 0.6006(2) 0.0683(8) Uani d . 1
H H14A 0.2690 0.0120 0.5853 0.082 Uiso calc R 1
H H14B 0.1270 -0.0622 0.5576 0.082 Uiso calc R 1
H H14C 0.4135 -0.0643 0.5947 0.082 Uiso calc R 1
N N1 -0.1132(3) 0.06164(9) 0.68444(12) 0.0371(4) Uani d . 1
H H1N -0.2573 0.0571 0.6536 0.044 Uiso calc R 1
O O1 0.3127(3) 0.12146(10) 0.67758(12) 0.0478(4) Uani d . 1
O O2 -0.0692(4) 0.17882(10) 0.59926(12) 0.0576(5) Uani d . 1
S S1 0.04474(9) 0.13941(3) 0.67748(3) 0.0358(2) 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 0.0181 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'
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
C6 C1 C2 120.9(2)
C6 C1 S1 119.41(16)
C2 C1 S1 119.71(18)
C1 C2 C3 118.3(3)
C1 C2 H2 120.8
C3 C2 H2 120.8
C4 C3 C2 120.8(2)
C4 C3 H3 119.6
C2 C3 H3 119.6
C5 C4 C3 120.5(3)
C5 C4 H4 119.8
C3 C4 H4 119.8
C4 C5 C6 120.0(3)
C4 C5 H5 120.0
C6 C5 H5 120.0
C1 C6 C5 119.5(2)
C1 C6 H6 120.2
C5 C6 H6 120.2
C8 C7 C12 121.8(2)
C8 C7 N1 119.69(19)
C12 C7 N1 118.5(2)
C9 C8 C7 118.2(2)
C9 C8 C13 119.5(2)
C7 C8 C13 122.3(2)
C10 C9 C8 121.0(3)
C10 C9 H9 119.5
C8 C9 H9 119.5
C11 C10 C9 120.0(3)
C11 C10 H10 120.0
C9 C10 H10 120.0
C10 C11 C12 121.7(3)
C10 C11 H11 119.2
C12 C11 H11 119.2
C11 C12 C7 117.3(3)
C11 C12 C14 119.8(2)
C7 C12 C14 122.9(2)
C8 C13 H13A 109.5
C8 C13 H13B 109.5
H13A C13 H13B 109.5
C8 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C7 N1 S1 121.72(13)
C7 N1 H1N 119.1
S1 N1 H1N 119.1
O2 S1 O1 119.85(11)
O2 S1 N1 105.89(10)
O1 S1 N1 107.55(10)
O2 S1 C1 107.95(11)
O1 S1 C1 106.89(10)
N1 S1 C1 108.28(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.376(3)
C1 C2 1.386(3)
C1 S1 1.765(2)
C2 C3 1.388(4)
C2 H2 0.9300
C3 C4 1.369(5)
C3 H3 0.9300
C4 C5 1.363(4)
C4 H4 0.9300
C5 C6 1.386(3)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.397(3)
C7 C12 1.398(3)
C7 N1 1.441(3)
C8 C9 1.386(3)
C8 C13 1.505(3)
C9 C10 1.377(5)
C9 H9 0.9300
C10 C11 1.368(5)
C10 H10 0.9300
C11 C12 1.397(4)
C11 H11 0.9300
C12 C14 1.508(4)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
N1 S1 1.6263(17)
N1 H1N 0.8600
O1 S1 1.4334(16)
O2 S1 1.4221(17)
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 O1 1_455 0.86 2.55 3.179(2) 130.5
C5 H5 O2 4_666 0.93 2.57 3.229(3) 128.5
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
C6 C1 C2 C3 -0.4(3)
S1 C1 C2 C3 178.70(18)
C1 C2 C3 C4 0.9(4)
C2 C3 C4 C5 -1.1(4)
C3 C4 C5 C6 0.7(4)
C2 C1 C6 C5 0.1(3)
S1 C1 C6 C5 -179.04(18)
C4 C5 C6 C1 -0.2(4)
C12 C7 C8 C9 2.6(3)
N1 C7 C8 C9 -179.8(2)
C12 C7 C8 C13 -175.8(2)
N1 C7 C8 C13 1.8(3)
C7 C8 C9 C10 -0.1(4)
C13 C8 C9 C10 178.3(3)
C8 C9 C10 C11 -1.7(5)
C9 C10 C11 C12 1.2(5)
C10 C11 C12 C7 1.2(4)
C10 C11 C12 C14 -176.0(3)
C8 C7 C12 C11 -3.2(3)
N1 C7 C12 C11 179.3(2)
C8 C7 C12 C14 174.0(2)
N1 C7 C12 C14 -3.5(3)
C8 C7 N1 S1 99.9(2)
C12 C7 N1 S1 -82.5(2)
C7 N1 S1 O2 165.74(17)
C7 N1 S1 O1 36.48(19)
C7 N1 S1 C1 -78.70(18)
C6 C1 S1 O2 -153.98(17)
C2 C1 S1 O2 26.9(2)
C6 C1 S1 O1 -23.8(2)
C2 C1 S1 O1 157.06(17)
C6 C1 S1 N1 91.81(18)
C2 C1 S1 N1 -87.33(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 260503
