#------------------------------------------------------------------------------
#$Date: 2008-03-30 13:21:05 +0300 (Sun, 30 Mar 2008) $
#$Revision: 321 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2015384.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_2015384
loop_
_publ_author_name
' Rahul Banerjee'
'Binoy K. Saha'
'Gautam R. Desiraju'
_publ_section_title
;
Solid-state architecture of saccharin salts of some diamines
;
_journal_coeditor_code           SF3006
_journal_issue                   6
_journal_name_full               'Acta Crystallographica, Section C'
_journal_page_first              o346
_journal_page_last               o349
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C4 H14 N2 2+, 2C7 H4 N O3 S -'
_chemical_formula_moiety         'C4 H14 N2 2+, 2C7 H4 N O3 S -'
_chemical_formula_sum            'C18 H22 N4 O6 S2'
_chemical_formula_weight         454.52
_chemical_name_common            ' saccharin, 1,4-butyldiamine'
_chemical_name_systematic
;
butane-1,4-diaminium bis(saccharinate)
;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   P21/n
_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                 109.1960(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.0016(11)
_cell_length_b                   11.2539(13)
_cell_length_c                   10.0269(12)
_cell_measurement_reflns_used    4341
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.06
_cell_measurement_theta_min      2.64
_cell_volume                     959.3(2)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       '\f and \w 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  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5206
_diffrn_reflns_theta_full        25.95
_diffrn_reflns_theta_max         25.95
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_T_max  0.9203
_exptl_absorpt_correction_T_min  0.8570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Siemens, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.454
_refine_ls_extinction_coef       0.036(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0438P)^2^+0.7096P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0830
_reflns_number_gt                1780
_reflns_number_total             1871
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    sf3006.cif
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_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_
_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
N N2 0.77564(15) 0.50781(13) 0.18396(14) 0.0162(3) Uani d . 1
C C9 0.92744(17) 0.52218(14) 0.01673(15) 0.0163(3) Uani d . 1
H H9A 0.9365 0.6089 0.0339 0.020 Uiso calc R 1
H H9B 0.8320 0.5075 -0.0656 0.020 Uiso calc R 1
C C8 0.91076(18) 0.45989(14) 0.14593(16) 0.0171(3) Uani d . 1
H H8A 0.8952 0.3737 0.1265 0.021 Uiso calc R 1
H H8B 1.0089 0.4704 0.2268 0.021 Uiso calc R 1
O O3 0.47033(12) 0.38723(10) 0.06019(11) 0.0179(3) Uani d . 1
S S1 0.48326(4) 0.26812(3) 0.11793(4) 0.01339(15) Uani d . 1
O O2 0.64212(12) 0.23881(10) 0.20604(11) 0.0175(3) Uani d . 1
C C7 0.34846(17) 0.25008(13) 0.20967(15) 0.0133(3) Uani d . 1
C C2 0.24053(17) 0.16557(13) 0.13613(14) 0.0139(3) Uani d . 1
C C1 0.28125(17) 0.12043(13) 0.01075(15) 0.0150(3) Uani d . 1
C C3 0.11468(17) 0.13566(14) 0.18006(15) 0.0160(3) Uani d . 1
H H3 0.0395 0.0781 0.1307 0.019 Uiso calc R 1
C C6 0.33885(18) 0.30757(14) 0.32847(15) 0.0161(3) Uani d . 1
H H6 0.4146 0.3650 0.3774 0.019 Uiso calc R 1
C C4 0.10214(18) 0.19295(14) 0.29909(16) 0.0181(3) Uani d . 1
H H4 0.0164 0.1743 0.3308 0.022 Uiso calc R 1
C C5 0.21249(18) 0.27709(14) 0.37284(16) 0.0183(3) Uani d . 1
H H5 0.2014 0.3140 0.4542 0.022 Uiso calc R 1
N N1 0.41263(15) 0.17045(12) -0.00215(13) 0.0172(3) Uani d . 1
H H2C 0.789(2) 0.585(2) 0.205(2) 0.028(5) Uiso d . 1
H H2B 0.762(2) 0.4708(19) 0.265(2) 0.033(6) Uiso d . 1
O O1 0.20080(12) 0.04441(10) -0.07077(11) 0.0179(3) Uani d . 1
H H2A 0.689(2) 0.4967(18) 0.115(2) 0.026(5) Uiso d . 1
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
N2 0.0149(6) 0.0183(7) 0.0156(6) -0.0021(5) 0.0052(5) 0.0001(5)
C9 0.0148(7) 0.0165(7) 0.0176(7) 0.0005(6) 0.0052(6) 0.0002(6)
C8 0.0152(7) 0.0177(8) 0.0189(7) 0.0013(6) 0.0062(6) 0.0009(6)
O3 0.0166(5) 0.0170(6) 0.0193(5) -0.0015(4) 0.0049(4) 0.0043(4)
S1 0.0117(2) 0.0149(2) 0.0137(2) -0.00089(13) 0.00433(15) 0.00097(13)
O2 0.0114(5) 0.0202(6) 0.0193(6) 0.0002(4) 0.0031(4) 0.0014(4)
C7 0.0108(7) 0.0145(7) 0.0146(7) 0.0009(5) 0.0041(6) 0.0034(5)
C2 0.0142(7) 0.0128(7) 0.0137(7) 0.0018(5) 0.0031(5) 0.0020(5)
C1 0.0146(7) 0.0154(7) 0.0143(7) 0.0025(6) 0.0040(6) 0.0029(6)
C3 0.0146(7) 0.0155(7) 0.0172(7) -0.0008(6) 0.0042(6) 0.0007(6)
C6 0.0169(7) 0.0148(7) 0.0150(7) 0.0006(6) 0.0029(6) 0.0002(6)
C4 0.0166(7) 0.0202(8) 0.0196(7) -0.0002(6) 0.0087(6) 0.0023(6)
C5 0.0200(8) 0.0202(8) 0.0154(7) 0.0021(6) 0.0068(6) -0.0005(6)
N1 0.0160(6) 0.0202(7) 0.0163(6) -0.0034(5) 0.0064(5) -0.0035(5)
O1 0.0182(5) 0.0186(6) 0.0168(5) -0.0039(4) 0.0057(4) -0.0039(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 C8 1.4902(19)
N2 H2C 0.89(2)
N2 H2B 0.96(2)
N2 H2A 0.87(2)
C9 C8 1.523(2)
C9 H9A 0.9900
C9 H9B 0.9900
C8 H8A 0.9900
C8 H8B 0.9900
O3 S1 1.4495(11)
S1 O2 1.4504(11)
S1 N1 1.5996(13)
S1 C7 1.7589(15)
C7 C6 1.383(2)
C7 C2 1.386(2)
C2 C3 1.385(2)
C2 C1 1.509(2)
C1 O1 1.2391(18)
C1 N1 1.3538(19)
C3 C4 1.393(2)
C3 H3 0.9500
C6 C5 1.394(2)
C6 H6 0.9500
C4 C5 1.395(2)
C4 H4 0.9500
C5 H5 0.9500
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 N2 H2C 110.7(13)
C8 N2 H2B 113.9(13)
H2C N2 H2B 105.4(18)
C8 N2 H2A 110.1(13)
H2C N2 H2A 110.5(19)
H2B N2 H2A 106.1(18)
C8 C9 H9A 109.3
C8 C9 H9B 109.3
H9A C9 H9B 108.0
N2 C8 C9 111.60(12)
N2 C8 H8A 109.3
C9 C8 H8A 109.3
N2 C8 H8B 109.3
C9 C8 H8B 109.3
H8A C8 H8B 108.0
O3 S1 O2 112.78(6)
O3 S1 N1 112.03(7)
O2 S1 N1 111.74(7)
O3 S1 C7 109.70(7)
O2 S1 C7 111.51(7)
N1 S1 C7 98.19(7)
C6 C7 C2 123.21(14)
C6 C7 S1 130.22(12)
C2 C7 S1 106.52(11)
C3 C2 C7 120.07(13)
C3 C2 C1 129.15(13)
C7 C2 C1 110.76(13)
O1 C1 N1 124.30(13)
O1 C1 C2 122.20(13)
N1 C1 C2 113.51(13)
C2 C3 C4 117.71(14)
C7 C6 C5 116.65(14)
C7 C6 H6 121.7
C5 C6 H6 121.7
C3 C4 C5 121.59(14)
C3 C4 H4 119.2
C5 C4 H4 119.2
C6 C5 C4 120.76(14)
C6 C5 H5 119.6
C4 C5 H5 119.6
C1 N1 S1 110.94(10)
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
N2 H2B O1 4_666 0.96(2) 1.91(2) 2.8173(17) 158.0(19)
N2 H2C O2 2_655 0.89(2) 1.96(2) 2.8259(18) 166.0(19)
N2 H2A O3 3_665 0.87(2) 2.28(2) 2.9540(17) 134.9(18)
N2 H2A O3 1 0.87(2) 2.23(2) 2.9482(17) 140.3(17)