#------------------------------------------------------------------------------
#$Date: 2011-09-10 05:16:28 +0200 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006221.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_2006221
loop_
_publ_author_name
'Dalluhn, J.'
'Henschel, D.'
'Blaschette, A.'
'Jones, P. G.'
_publ_section_title
;
 Polysulfonylamines. LXXXII. Oxalyl Chloride Dimesylamide
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              781
_journal_page_last               783
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C4 H6 Cl N O6 S2'
_chemical_formula_weight         263.67
_chemical_name_systematic
;
 Oxalyl chloride dimesylamide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.939(2)
_cell_length_b                   9.360(2)
_cell_length_c                   11.438(2)
_cell_measurement_reflns_used    56
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      11.5
_cell_measurement_theta_min      10
_cell_volume                     957.0(3)
_computing_cell_refinement       DIF4
_computing_data_collection       'DIF4 (Stoe & Cie, 1991a)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1991b)'
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      143(2)
_diffrn_measurement_device       'Stoe STADI-4'
_diffrn_measurement_method       '\w/\q 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  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2418
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.839
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.830
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.220
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_coef       0.0221(14)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.073
_refine_ls_goodness_of_fit_obs   1.075
_refine_ls_hydrogen_treatment    'H atoms: methyls refined as rigid groups'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.167
_refine_ls_restrained_S_obs      1.075
_refine_ls_R_factor_all          0.0208
_refine_ls_R_factor_obs          0.0201
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0297P)^2^+0.2238P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.0575
_refine_ls_wR_factor_obs         0.0526
_reflns_number_observed          2162
_reflns_number_total             2195
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    fg1267.cif
_[local]_cod_data_source_block   ben
_cod_database_code               2006221
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
N1 0.0217(6) 0.0197(6) 0.0153(5) 0.0006(5) 0.0025(4) -0.0002(5)
S1 0.0200(2) 0.0265(2) 0.0153(2) 0.00188(14) 0.00170(13) -0.00006(14)
S2 0.0201(2) 0.0226(2) 0.0217(2) 0.00346(14) 0.00083(13) -0.00233(14)
O1 0.0291(6) 0.0357(6) 0.0262(6) -0.0050(5) 0.0069(5) 0.0029(5)
O2 0.0286(6) 0.0306(6) 0.0241(6) 0.0079(5) 0.0010(5) -0.0035(5)
O3 0.0278(6) 0.0418(7) 0.0360(7) 0.0008(6) 0.0112(5) -0.0112(6)
O4 0.0393(7) 0.0287(6) 0.0309(6) 0.0103(5) -0.0059(6) 0.0024(5)
C1 0.0300(8) 0.0390(9) 0.0196(7) 0.0047(8) -0.0081(6) -0.0010(7)
C2 0.0282(8) 0.0238(8) 0.0314(8) -0.0021(7) -0.0042(7) -0.0032(7)
C3 0.0236(7) 0.0231(7) 0.0200(7) -0.0021(6) 0.0011(6) 0.0018(6)
C4 0.0287(8) 0.0226(7) 0.0220(7) -0.0031(7) 0.0061(6) 0.0014(5)
O5 0.0531(8) 0.0324(6) 0.0182(5) -0.0076(6) -0.0025(5) 0.0023(5)
O6 0.0345(6) 0.0348(7) 0.0325(7) -0.0104(6) -0.0020(6) -0.0042(5)
Cl 0.0594(3) 0.0258(2) 0.0483(3) 0.0062(2) -0.0068(2) 0.0062(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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
N1 0.49951(14) 0.41739(14) 0.48450(10) 0.0189(2) Uani d . 1 N
S1 0.57952(4) 0.39575(4) 0.34920(3) 0.02059(9) Uani d . 1 S
S2 0.46036(4) 0.58510(4) 0.53775(3) 0.02149(10) Uani d . 1 S
O1 0.67687(14) 0.51367(14) 0.33207(11) 0.0303(3) Uani d . 1 O
O2 0.64085(14) 0.25469(13) 0.35360(11) 0.0278(3) Uani d . 1 O
O3 0.34708(14) 0.5654(2) 0.62251(11) 0.0352(3) Uani d . 1 O
O4 0.4298(2) 0.66835(13) 0.43634(11) 0.0330(3) Uani d . 1 O
C1 0.4283(2) 0.4036(2) 0.25294(13) 0.0295(3) Uani d . 1 C
H1A 0.3549 0.3303 0.2741 0.035 Uiso calc R 1 H
H1B 0.4635 0.3868 0.1730 0.035 Uiso calc R 1 H
H1C 0.3816 0.4981 0.2577 0.035 Uiso calc R 1 H
C2 0.6279(2) 0.6369(2) 0.6040(2) 0.0278(3) Uani d . 1 C
H2A 0.7057 0.6474 0.5442 0.033 Uiso calc R 1 H
H2B 0.6585 0.5640 0.6607 0.033 Uiso calc R 1 H
H2C 0.6135 0.7283 0.6443 0.033 Uiso calc R 1 H
C3 0.5005(2) 0.3029(2) 0.56440(14) 0.0222(3) Uani d . 1 C
C4 0.4578(2) 0.1568(2) 0.51329(14) 0.0244(3) Uani d . 1 C
O5 0.5185(2) 0.31683(14) 0.66708(10) 0.0346(3) Uani d . 1 O
O6 0.35879(15) 0.13859(14) 0.44719(12) 0.0339(3) Uani d . 1 O
Cl 0.55941(7) 0.01965(5) 0.57711(5) 0.04449(14) Uani d . 1 Cl
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'
Cl Cl 0.1484 0.1585 '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
C3 N1 S1 119.51(11) y
C3 N1 S2 117.78(10) y
S1 N1 S2 120.77(7) y
O1 S1 O2 119.19(8) ?
O1 S1 N1 106.75(7) ?
O2 S1 N1 103.70(7) ?
O1 S1 C1 110.80(9) ?
O2 S1 C1 110.97(8) ?
N1 S1 C1 103.95(7) ?
O3 S2 O4 119.51(8) ?
O3 S2 N1 105.64(7) ?
O4 S2 N1 104.48(7) ?
O3 S2 C2 110.65(8) ?
O4 S2 C2 111.46(9) ?
N1 S2 C2 103.44(7) ?
O5 C3 N1 123.8(2) y
O5 C3 C4 120.40(15) y
N1 C3 C4 115.40(13) y
O6 C4 C3 124.1(2) y
O6 C4 Cl 123.85(14) y
C3 C4 Cl 111.66(12) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C3 1.408(2) y
N1 S1 1.7168(12) y
N1 S2 1.7198(14) y
S1 O1 1.4191(13) y
S1 O2 1.4305(12) y
S1 C1 1.745(2) y
S2 O3 1.4140(13) y
S2 O4 1.4237(13) y
S2 C2 1.747(2) y
C3 O5 1.192(2) y
C3 C4 1.535(2) y
C4 O6 1.177(2) y
C4 Cl 1.734(2) y
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
C3 N1 S1 O1 -129.99(12)
S2 N1 S1 O1 33.80(10)
C3 N1 S1 O2 -3.29(13)
S2 N1 S1 O2 160.49(9)
C3 N1 S1 C1 112.82(13)
S2 N1 S1 C1 -83.39(10)
C3 N1 S2 O3 -38.68(13)
S1 N1 S2 O3 157.26(9)
C3 N1 S2 O4 -165.58(12)
S1 N1 S2 O4 30.36(11)
C3 N1 S2 C2 77.65(13)
S1 N1 S2 C2 -86.41(10)
S1 N1 C3 O5 142.1(2)
S2 N1 C3 O5 -22.2(2)
S1 N1 C3 C4 -45.0(2)
S2 N1 C3 C4 150.76(11)
O5 C3 C4 O6 130.7(2)
N1 C3 C4 O6 -42.5(2)
O5 C3 C4 Cl -42.5(2)
N1 C3 C4 Cl 144.29(11)