#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/58/2205870.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_2205870
loop_
_publ_author_name
'G. Usha'
'S. Selvanayagam'
'D. Velmurugan'
'K. Ravikumar'
'P. Jaisankar'
'P. C. Srinivasan'
_publ_section_title
;
 N-Butyl-N-o-tolylbenzenesulfonamide
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1916
_journal_page_last               o1918
_journal_paper_doi               10.1107/S160053680501562X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C17 H21 N O2 S'
_chemical_formula_moiety         'C17 H21 N O2 S'
_chemical_formula_sum            'C17 H21 N O2 S'
_chemical_formula_weight         303.41
_chemical_name_systematic
;
N-Butyl-N-o-tolyl-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                 99.382(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2614(9)
_cell_length_b                   18.4306(19)
_cell_length_c                   9.8602(10)
_cell_measurement_reflns_used    2765
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2.2
_cell_volume                     1660.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device       'Bruker SMART APEX area-detector'
_diffrn_measurement_device_type  'CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9999
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.215
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3635
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0611
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1P)²+0.3505P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1655
_refine_ls_wR_factor_ref         0.1794
_reflns_number_gt                2765
_reflns_number_total             3635
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6659.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (8
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (9
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (4 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (8
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (9
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (4 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2205870
_cod_database_fobs_code          2205870
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_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
S1 0.63749(6) 0.13146(3) 0.45717(6) 0.0555(2) Uani d . 1 S
O1 0.49855(17) 0.09665(11) 0.4499(2) 0.0763(5) Uani d . 1 O
O2 0.6445(2) 0.20749(9) 0.4342(2) 0.0721(5) Uani d . 1 O
N1 0.72100(19) 0.09188(9) 0.34317(19) 0.0521(5) Uani d . 1 N
C1 0.8570(2) 0.12466(10) 0.3183(2) 0.0508(5) Uani d . 1 C
C2 0.9873(2) 0.10479(13) 0.3998(3) 0.0601(6) Uani d . 1 C
H2 0.9862 0.0719 0.4712 0.072 Uiso calc R 1 H
C3 1.1180(3) 0.13304(16) 0.3762(4) 0.0804(8) Uani d . 1 C
H3 1.2052 0.1190 0.4307 0.097 Uiso calc R 1 H
C4 1.1192(4) 0.1813(2) 0.2735(4) 0.0990(12) Uani d . 1 C
H4 1.2077 0.2005 0.2573 0.119 Uiso calc R 1 H
C5 0.9915(5) 0.20217(17) 0.1931(3) 0.0947(11) Uani d . 1 C
H5 0.9954 0.2358 0.1234 0.114 Uiso calc R 1 H
C6 0.8534(3) 0.17445(13) 0.2120(3) 0.0691(7) Uani d . 1 C
C7 0.7165(5) 0.1969(2) 0.1234(3) 0.1041(11) Uani d . 1 C
H7A 0.6553 0.1553 0.1002 0.156 Uiso calc R 1 H
H7B 0.7391 0.2186 0.0408 0.156 Uiso calc R 1 H
H7C 0.6662 0.2315 0.1715 0.156 Uiso calc R 1 H
C8 0.7392(2) 0.11350(12) 0.6200(2) 0.0525(5) Uani d . 1 C
C9 0.8419(3) 0.16331(13) 0.6812(3) 0.0633(6) Uani d . 1 C
H9 0.8563 0.2065 0.6366 0.076 Uiso calc R 1 H
C10 0.9219(3) 0.14852(16) 0.8076(3) 0.0779(8) Uani d . 1 C
H10 0.9908 0.1818 0.8491 0.094 Uiso calc R 1 H
C11 0.9006(4) 0.08500(18) 0.8727(3) 0.0862(9) Uani d . 1 C
H11 0.9543 0.0755 0.9590 0.103 Uiso calc R 1 H
C12 0.8003(4) 0.03488(17) 0.8116(3) 0.0846(9) Uani d . 1 C
H12 0.7879 -0.0086 0.8563 0.102 Uiso calc R 1 H
C13 0.7192(3) 0.04848(13) 0.6861(3) 0.0662(7) Uani d . 1 C
H13 0.6513 0.0147 0.6450 0.079 Uiso calc R 1 H
C14 0.7113(3) 0.01170(12) 0.3346(3) 0.0618(6) Uani d . 1 C
H14A 0.8001 -0.0090 0.3858 0.074 Uiso calc R 1 H
H14B 0.6300 -0.0044 0.3777 0.074 Uiso calc R 1 H
C15 0.6912(4) -0.01596(14) 0.1925(3) 0.0825(8) Uani d . 1 C
H15A 0.7752 -0.0026 0.1507 0.099 Uiso calc R 1 H
H15B 0.6053 0.0065 0.1396 0.099 Uiso calc R 1 H
C16 0.6730(4) -0.09852(16) 0.1876(4) 0.0993(11) Uani d . 1 C
H16A 0.7575 -0.1203 0.2441 0.119 Uiso calc R 1 H
H16B 0.5875 -0.1112 0.2279 0.119 Uiso calc R 1 H
C17 0.6570(6) -0.1300(2) 0.0497(5) 0.1449(19) Uani d . 1 C
H17A 0.5797 -0.1056 -0.0097 0.217 Uiso calc R 1 H
H17B 0.6340 -0.1807 0.0540 0.217 Uiso calc R 1 H
H17C 0.7470 -0.1244 0.0142 0.217 Uiso calc R 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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
_geom_angle_publ_flag
O2 S1 O1 119.90(10) y
O2 S1 N1 106.90(10) y
O1 S1 N1 106.70(10) y
O2 S1 C8 107.40(10) y
O1 S1 C8 107.80(10) y
N1 S1 C8 107.50(10) y
C1 N1 C14 116.8(2) y
C1 N1 S1 116.80(10) y
C14 N1 S1 116.90(10) y
C2 C1 C6 121.6(2) ?
C2 C1 N1 119.31(19) ?
C6 C1 N1 119.1(2) ?
C3 C2 C1 120.7(3) ?
C3 C2 H2 119.6 ?
C1 C2 H2 119.6 ?
C4 C3 C2 119.5(3) ?
C4 C3 H3 120.2 ?
C2 C3 H3 120.2 ?
C3 C4 C5 120.6(3) ?
C3 C4 H4 119.7 ?
C5 C4 H4 119.7 ?
C4 C5 C6 122.4(3) ?
C4 C5 H5 118.8 ?
C6 C5 H5 118.8 ?
C1 C6 C5 115.2(3) ?
C1 C6 C7 123.0(3) ?
C5 C6 C7 121.8(3) ?
C6 C7 H7A 109.5 ?
C6 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C6 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
C9 C8 C13 120.0(2) ?
C9 C8 S1 120.06(19) ?
C13 C8 S1 119.92(18) ?
C10 C9 C8 119.7(2) ?
C10 C9 H9 120.2 ?
C8 C9 H9 120.2 ?
C11 C10 C9 120.0(3) ?
C11 C10 H10 120.0 ?
C9 C10 H10 120.0 ?
C10 C11 C12 120.6(3) ?
C10 C11 H11 119.7 ?
C12 C11 H11 119.7 ?
C13 C12 C11 120.4(3) ?
C13 C12 H12 119.8 ?
C11 C12 H12 119.8 ?
C12 C13 C8 119.3(2) ?
C12 C13 H13 120.4 ?
C8 C13 H13 120.4 ?
C15 C14 N1 113.4(2) ?
C15 C14 H14A 108.9 ?
N1 C14 H14A 108.9 ?
C15 C14 H14B 108.9 ?
N1 C14 H14B 108.9 ?
H14A C14 H14B 107.7 ?
C14 C15 C16 111.7(3) ?
C14 C15 H15A 109.3 ?
C16 C15 H15A 109.3 ?
C14 C15 H15B 109.3 ?
C16 C15 H15B 109.3 ?
H15A C15 H15B 107.9 ?
C17 C16 C15 114.7(3) ?
C17 C16 H16A 108.6 ?
C15 C16 H16A 108.6 ?
C17 C16 H16B 108.6 ?
C15 C16 H16B 108.6 ?
H16A C16 H16B 107.6 ?
C16 C17 H17A 109.5 ?
C16 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C16 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O2 1.423(2) y
S1 O1 1.429(2) y
S1 N1 1.636(2) y
S1 C8 1.755(3) y
N1 C1 1.454(3) y
N1 C14 1.482(3) y
C1 C2 1.385(3) ?
C1 C6 1.390(3) ?
C2 C3 1.372(3) ?
C2 H2 0.9300 ?
C3 C4 1.349(5) ?
C3 H3 0.9300 ?
C4 C5 1.368(5) ?
C4 H4 0.9300 ?
C5 C6 1.417(4) ?
C5 H5 0.9300 ?
C6 C7 1.477(5) y
C7 H7A 0.9600 ?
C7 H7B 0.9600 ?
C7 H7C 0.9600 ?
C8 C9 1.387(3) ?
C8 C13 1.391(3) ?
C9 C10 1.369(4) ?
C9 H9 0.9300 ?
C10 C11 1.365(4) ?
C10 H10 0.9300 ?
C11 C12 1.377(4) ?
C11 H11 0.9300 ?
C12 C13 1.362(4) ?
C12 H12 0.9300 ?
C13 H13 0.9300 ?
C14 C15 1.473(4) ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C15 C16 1.531(4) y
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 C17 1.464(5) ?
C16 H16A 0.9700 ?
C16 H16B 0.9700 ?
C17 H17A 0.9600 ?
C17 H17B 0.9600 ?
C17 H17C 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
C10 H10 O2 4_666 0.93 2.55 3.466(3) 168
C13 H13 O1 3_656 0.93 2.57 3.484(3) 169
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
O2 S1 N1 C1 42.44(19) ?
O1 S1 N1 C1 171.89(16) ?
C8 S1 N1 C1 -72.67(18) ?
O2 S1 N1 C14 -172.24(17) ?
O1 S1 N1 C14 -42.8(2) ?
C8 S1 N1 C14 72.7(2) y
C14 N1 C1 C2 -58.0(3) ?
S1 N1 C1 C2 87.3(2) ?
C14 N1 C1 C6 121.0(2) ?
S1 N1 C1 C6 -93.6(2) ?
C6 C1 C2 C3 -1.1(4) ?
N1 C1 C2 C3 178.0(2) ?
C1 C2 C3 C4 0.7(4) ?
C2 C3 C4 C5 0.0(5) ?
C3 C4 C5 C6 -0.5(5) ?
C2 C1 C6 C5 0.6(3) ?
N1 C1 C6 C5 -178.4(2) ?
C2 C1 C6 C7 -179.9(3) ?
N1 C1 C6 C7 1.1(4) ?
C4 C5 C6 C1 0.1(4) ?
C4 C5 C6 C7 -179.4(3) ?
O2 S1 C8 C9 -19.5(2) ?
O1 S1 C8 C9 -149.98(18) ?
N1 S1 C8 C9 95.3(2) y
O2 S1 C8 C13 162.08(18) ?
O1 S1 C8 C13 31.6(2) ?
N1 S1 C8 C13 -83.2(2) y
C13 C8 C9 C10 -0.9(4) ?
S1 C8 C9 C10 -179.3(2) ?
C8 C9 C10 C11 0.1(4) ?
C9 C10 C11 C12 0.9(5) ?
C10 C11 C12 C13 -1.0(5) ?
C11 C12 C13 C8 0.2(5) ?
C9 C8 C13 C12 0.7(4) ?
S1 C8 C13 C12 179.1(2) ?
C1 N1 C14 C15 -74.7(3) ?
S1 N1 C14 C15 140.0(2) ?
N1 C14 C15 C16 -176.8(2) ?
C14 C15 C16 C17 -178.2(3) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9697122
