#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008496.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_2008496
loop_
_publ_author_name
'Linden, A.'
'Bienz, S.'
_publ_section_title
;
 <i>N</i>,<i>N</i>'-Dibenzenesulfonylputrescine
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              IUC9900046
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C16 H20 N2 O4 S2'
_chemical_formula_sum            'C16 H20 N2 O4 S2'
_chemical_formula_weight         368.46
_chemical_melting_point          403.8(4)
_chemical_name_common            N,N'-dibenzenesulfonylputrescine
_chemical_name_systematic
;
N-{4-[(benzenesulfonyl)amino]butyl}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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.705(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.649(2)
_cell_length_b                   5.8777(16)
_cell_length_c                   14.8257(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20.0
_cell_measurement_theta_min      18.5
_cell_volume                     884.0(3)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular Structure
Corporation, 1991)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1989)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997b)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku AFC-5R'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode generator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2339
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         2025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.060
_refine_ls_R_factor_gt           0.036
_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/[\s^2^(Fo^2^)+(0.0522P)^2^+0.2504P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.105
_reflns_number_gt                1541
_reflns_number_total             2025
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    qa0111.cif
_[local]_cod_data_source_block   QA0111
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '403.4-404.1' was changed to
'403.8(4)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2008496
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 0.82476(4) -0.00661(8) 0.13216(3) 0.02752(15) Uani d . 1 S
O1 0.82203(14) -0.1007(3) 0.04256(10) 0.0399(4) Uani d . 1 O
O2 0.83649(14) -0.1564(2) 0.21081(10) 0.0401(4) Uani d . 1 O
N1 0.68807(14) 0.1311(3) 0.11752(11) 0.0274(3) Uani d . 1 N
H1 0.677(2) 0.168(4) 0.1709(16) 0.045(7) Uiso d . 1 H
C2 0.65789(18) 0.3216(3) 0.04969(14) 0.0327(4) Uani d . 1 C
H21 0.6729 0.2741 -0.0103 0.039 Uiso calc R 1 H
H22 0.7170 0.4514 0.0759 0.039 Uiso calc R 1 H
C3 0.51554(18) 0.3939(3) 0.03070(13) 0.0310(4) Uani d . 1 C
H31 0.4985 0.4243 0.0916 0.037 Uiso calc R 1 H
H32 0.4567 0.2686 -0.0014 0.037 Uiso calc R 1 H
C4 0.95358(17) 0.1950(3) 0.16515(13) 0.0281(4) Uani d . 1 C
C5 1.01814(19) 0.2573(4) 0.10059(14) 0.0359(5) Uani d . 1 C
H5 0.9969 0.1865 0.0402 0.043 Uiso calc R 1 H
C6 1.1143(2) 0.4248(4) 0.12567(16) 0.0463(6) Uani d . 1 C
H6 1.1590 0.4697 0.0820 0.056 Uiso calc R 1 H
C7 1.1453(2) 0.5263(4) 0.21338(18) 0.0476(6) Uani d . 1 C
H7 1.2114 0.6405 0.2300 0.057 Uiso calc R 1 H
C8 1.0806(2) 0.4629(4) 0.27746(16) 0.0436(5) Uani d . 1 C
H8 1.1027 0.5332 0.3380 0.052 Uiso calc R 1 H
C9 0.9841(2) 0.2978(3) 0.25369(14) 0.0356(4) Uani d . 1 C
H9 0.9390 0.2548 0.2973 0.043 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0315(3) 0.0258(2) 0.0290(2) 0.00194(18) 0.01481(18) 0.00210(18)
O1 0.0459(8) 0.0398(8) 0.0415(8) -0.0061(7) 0.0243(7) -0.0120(7)
O2 0.0428(8) 0.0357(8) 0.0471(9) 0.0073(6) 0.0214(7) 0.0166(7)
N1 0.0281(8) 0.0306(8) 0.0258(8) 0.0029(6) 0.0118(6) 0.0035(6)
C2 0.0307(9) 0.0344(10) 0.0321(10) -0.0001(8) 0.0083(8) 0.0091(8)
C3 0.0278(9) 0.0326(10) 0.0293(9) -0.0021(8) 0.0039(7) 0.0041(8)
C4 0.0264(8) 0.0285(9) 0.0299(9) 0.0050(7) 0.0090(7) 0.0036(8)
C5 0.0344(10) 0.0427(11) 0.0320(10) -0.0013(9) 0.0121(8) 0.0054(9)
C6 0.0383(12) 0.0518(13) 0.0507(13) -0.0066(10) 0.0164(10) 0.0103(11)
C7 0.0346(11) 0.0358(12) 0.0666(16) -0.0049(9) 0.0067(10) 0.0025(11)
C8 0.0394(11) 0.0405(12) 0.0460(12) 0.0048(10) 0.0055(10) -0.0109(10)
C9 0.0366(10) 0.0373(10) 0.0343(10) 0.0070(9) 0.0130(8) -0.0023(9)
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 for Crystallography (1992).
Vol.C, Tables 4.2.6.8 and 6.1.1.4
;
H H 0.0000 0.0000
; International Tables for Crystallography (1992).
Vol.C, Tables 4.2.6.8 and 6.1.1.4
;
N N 0.0061 0.0033
; International Tables for Crystallography (1992).
Vol.C, Tables 4.2.6.8 and 6.1.1.4
;
O O 0.0106 0.0060
; International Tables for Crystallography (1992).
Vol.C, Tables 4.2.6.8 and 6.1.1.4
;
S S 0.1246 0.1234
; International Tables for Crystallography (1992).
Vol.C, Tables 4.2.6.8 and 6.1.1.4
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 -2 0
-2 -1 -1
-2 -1 -2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . 119.27(10) yes
O1 S1 N1 . . 107.74(9) ?
O2 S1 N1 . . 105.52(8) ?
O1 S1 C4 . . 108.14(9) ?
O2 S1 C4 . . 108.55(9) ?
N1 S1 C4 . . 107.01(9) yes
C2 N1 S1 . . 118.11(12) yes
C2 N1 H1 . . 111.7(16) ?
S1 N1 H1 . . 112.0(15) ?
N1 C2 C3 . . 109.76(15) ?
N1 C2 H21 . . 109.7 ?
C3 C2 H21 . . 109.7 ?
N1 C2 H22 . . 109.7 ?
C3 C2 H22 . . 109.7 ?
H21 C2 H22 . . 108.2 ?
C2 C3 C3 . 3_665 111.4(2) ?
C2 C3 H31 . . 109.3 ?
C3 C3 H31 3_665 . 109.3 ?
C2 C3 H32 . . 109.3 ?
C3 C3 H32 3_665 . 109.3 ?
H31 C3 H32 . . 108.0 ?
C5 C4 C9 . . 120.90(19) ?
C5 C4 S1 . . 119.52(15) ?
C9 C4 S1 . . 119.49(14) ?
C6 C5 C4 . . 118.9(2) ?
C6 C5 H5 . . 120.6 ?
C4 C5 H5 . . 120.6 ?
C7 C6 C5 . . 120.4(2) ?
C7 C6 H6 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
C6 C7 C8 . . 120.4(2) ?
C6 C7 H7 . . 119.8 ?
C8 C7 H7 . . 119.8 ?
C9 C8 C7 . . 120.1(2) ?
C9 C8 H8 . . 119.9 ?
C7 C8 H8 . . 119.9 ?
C8 C9 C4 . . 119.30(19) ?
C8 C9 H9 . . 120.4 ?
C4 C9 H9 . . 120.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . 1.4310(14) ?
S1 O2 . 1.4361(14) ?
S1 N1 . 1.6213(16) yes
S1 C4 . 1.7654(19) yes
N1 C2 . 1.474(2) yes
N1 H1 . 0.87(2) ?
C2 C3 . 1.516(3) ?
C2 H21 . 0.9900 ?
C2 H22 . 0.9900 ?
C3 C3 3_665 1.520(4) ?
C3 H31 . 0.9900 ?
C3 H32 . 0.9900 ?
C4 C5 . 1.387(3) ?
C4 C9 . 1.391(3) ?
C5 C6 . 1.387(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.376(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.383(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.379(3) ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
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
_geom_hbond_publ_flag
N1 H1 O2 2_655 0.87(2) 2.07(2) 2.917(2) 164(2) yes
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_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 N1 C2 . -59.85(16) ?
O2 S1 N1 C2 . 171.72(14) ?
C4 S1 N1 C2 . 56.23(16) yes
S1 N1 C2 C3 . 167.96(13) yes
N1 C2 C3 C3 3_665 173.93(19) yes
O1 S1 C4 C5 . 8.70(18) ?
O2 S1 C4 C5 . 139.44(16) ?
N1 S1 C4 C5 . -107.12(16) yes
O1 S1 C4 C9 . -174.70(15) ?
O2 S1 C4 C9 . -43.96(18) ?
N1 S1 C4 C9 . 69.48(17) ?
C9 C4 C5 C6 . 0.0(3) ?
S1 C4 C5 C6 . 176.56(16) ?
C4 C5 C6 C7 . 0.3(3) ?
C5 C6 C7 C8 . -0.2(3) ?
C6 C7 C8 C9 . -0.2(3) ?
C7 C8 C9 C4 . 0.5(3) ?
C5 C4 C9 C8 . -0.4(3) ?
S1 C4 C9 C8 . -176.98(15) ?