#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/83/2008325.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_2008325
loop_
_publ_author_name
'Henschel, Dagmar'
'Wijaya, Karna'
'Jones, Peter G.'
'Blaschette, Armand'
_publ_section_title
;
 Polysulfonylamines. CX. Hydroxylammonium di(methanesulfonyl)amidate
 1,4,7,10,13,16-hexaoxacyclooctadecane (1/1/1) and 2-aminopyridinium
 di(methanesulfonyl)amidate 1,4,7,10,13,16-hexaoxacyclooctadecane
 (1/1/1)
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              664
_journal_page_last               668
_journal_paper_doi               10.1107/S0108270199001274
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'H4 N O +, C2 H6 N O4 S2 -, C12 H24 O6'
_chemical_formula_sum            'C14 H34 N2 O11 S2'
_chemical_formula_weight         470.55
_chemical_name_systematic        ?
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.5888(12)
_cell_length_b                   8.1378(10)
_cell_length_c                   28.964(2)
_cell_measurement_reflns_used    64
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      3.0
_cell_volume                     4381.4(7)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Fait, 1991)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens P4'
_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_sigmaI/netI    0.049
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            3848
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         3.02
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 247
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.29
_refine_ls_extinction_coef       0.00039(12)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3848
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.883
_refine_ls_R_factor_all          0.058
_refine_ls_R_factor_gt           0.033
_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)+(0.0382P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.074
_reflns_number_gt                2631
_reflns_number_total             3848
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm1316.cif
_cod_data_source_block           II
_cod_database_code               2008325
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'
'-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_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 0.41549(9) 0.2210(2) 0.39244(6) 0.0235(4) Uani d . 1 . . N
S1 0.37943(3) 0.33544(7) 0.431674(18) 0.02637(14) Uani d . 1 . . S
S2 0.36759(3) 0.09707(7) 0.362571(18) 0.02393(14) Uani d . 1 . . S
O1 0.43803(9) 0.4008(2) 0.45833(5) 0.0439(5) Uani d . 1 . . O
O2 0.32282(9) 0.2518(2) 0.45625(5) 0.0397(4) Uani d . 1 . . O
O3 0.41451(9) 0.03889(19) 0.32653(5) 0.0372(4) Uani d . 1 . . O
O4 0.29962(8) 0.16666(19) 0.34827(5) 0.0323(4) Uani d . 1 . . O
C1 0.34060(13) 0.5010(3) 0.40171(8) 0.0336(6) Uani d . 1 . . C
H1A 0.3154 0.5726 0.4236 0.040 Uiso calc R 1 . . H
H1B 0.3064 0.4590 0.3788 0.040 Uiso calc R 1 . . H
H1C 0.3784 0.5636 0.3860 0.040 Uiso calc R 1 . . H
C2 0.34900(13) -0.0718(3) 0.39859(8) 0.0328(6) Uani d . 1 . . C
H2A 0.3226 -0.0343 0.4259 0.039 Uiso calc R 1 . . H
H2B 0.3943 -0.1232 0.4082 0.039 Uiso calc R 1 . . H
H2C 0.3198 -0.1521 0.3817 0.039 Uiso calc R 1 . . H
C11 0.66727(12) 0.3546(3) 0.25479(7) 0.0271(5) Uani d . 1 . . C
H11A 0.6966 0.4324 0.2364 0.033 Uiso calc R 1 . . H
H11B 0.6191 0.4035 0.2595 0.033 Uiso calc R 1 . . H
C12 0.66059(12) 0.1944(3) 0.22966(7) 0.0262(5) Uani d . 1 . . C
H12A 0.6407 0.2133 0.1984 0.031 Uiso calc R 1 . . H
H12B 0.7086 0.1429 0.2264 0.031 Uiso calc R 1 . . H
C13 0.61178(12) -0.0740(3) 0.23657(7) 0.0288(5) Uani d . 1 . . C
H13A 0.6595 -0.1270 0.2399 0.035 Uiso calc R 1 . . H
H13B 0.5996 -0.0699 0.2033 0.035 Uiso calc R 1 . . H
C14 0.55645(12) -0.1707(3) 0.26196(7) 0.0287(5) Uani d . 1 . . C
H14A 0.5094 -0.1140 0.2602 0.034 Uiso calc R 1 . . H
H14B 0.5512 -0.2806 0.2477 0.034 Uiso calc R 1 . . H
C15 0.52838(12) -0.2862(3) 0.33427(7) 0.0273(5) Uani d . 1 . . C
H15A 0.5261 -0.3976 0.3207 0.033 Uiso calc R 1 . . H
H15B 0.4797 -0.2371 0.3328 0.033 Uiso calc R 1 . . H
C16 0.55241(12) -0.2968(3) 0.38336(7) 0.0278(5) Uani d . 1 . . C
H16A 0.5205 -0.3721 0.4007 0.033 Uiso calc R 1 . . H
H16B 0.6021 -0.3405 0.3848 0.033 Uiso calc R 1 . . H
C17 0.57331(12) -0.1393(3) 0.45028(7) 0.0270(5) Uani d . 1 . . C
H17A 0.6220 -0.1880 0.4522 0.032 Uiso calc R 1 . . H
H17B 0.5401 -0.2076 0.4689 0.032 Uiso calc R 1 . . H
C18 0.57457(12) 0.0320(3) 0.46870(7) 0.0283(5) Uani d . 1 . . C
H18A 0.5280 0.0866 0.4623 0.034 Uiso calc R 1 . . H
H18B 0.5820 0.0298 0.5025 0.034 Uiso calc R 1 . . H
C19 0.63828(13) 0.2822(3) 0.46550(8) 0.0359(6) Uani d . 1 . . C
H19A 0.6457 0.2774 0.4993 0.043 Uiso calc R 1 . . H
H19B 0.5941 0.3463 0.4593 0.043 Uiso calc R 1 . . H
C20 0.70149(13) 0.3616(3) 0.44271(7) 0.0362(6) Uani d . 1 . . C
H20A 0.7096 0.4723 0.4559 0.043 Uiso calc R 1 . . H
H20B 0.7453 0.2948 0.4478 0.043 Uiso calc R 1 . . H
C21 0.74499(12) 0.4394(3) 0.36867(7) 0.0294(5) Uani d . 1 . . C
H21A 0.7851 0.3594 0.3676 0.035 Uiso calc R 1 . . H
H21B 0.7627 0.5415 0.3833 0.035 Uiso calc R 1 . . H
C22 0.71916(12) 0.4753(3) 0.32064(7) 0.0290(5) Uani d . 1 . . C
H22A 0.6766 0.5484 0.3219 0.035 Uiso calc R 1 . . H
H22B 0.7575 0.5321 0.3030 0.035 Uiso calc R 1 . . H
O11 0.61405(8) 0.08859(18) 0.25509(5) 0.0246(3) Uani d . 1 . . O
O12 0.57779(7) -0.18747(18) 0.30899(5) 0.0262(4) Uani d . 1 . . O
O13 0.54997(8) -0.13639(17) 0.40333(4) 0.0253(4) Uani d . 1 . . O
O14 0.63142(8) 0.12080(18) 0.44719(5) 0.0283(4) Uani d . 1 . . O
O15 0.68682(8) 0.37373(19) 0.39471(5) 0.0298(4) Uani d . 1 . . O
O16 0.70062(7) 0.32560(17) 0.29815(5) 0.0248(3) Uani d . 1 . . O
N2 0.58188(11) 0.1609(2) 0.35006(7) 0.0246(4) Uani d D 1 . . N
H02 0.5944(15) 0.128(4) 0.3211(7) 0.077(10) Uiso d D 1 . . H
H03 0.5628(15) 0.066(3) 0.3620(9) 0.074(10) Uiso d D 1 . . H
H04 0.6212(14) 0.183(4) 0.3685(10) 0.099(12) Uiso d D 1 . . H
O5 0.53586(9) 0.2981(2) 0.34653(6) 0.0355(4) Uani d . 1 . . O
H01 0.4970(16) 0.272(4) 0.3653(10) 0.072(10) Uiso d . 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
S2 N1 S1 120.87(11)
O1 S1 O2 117.57(10)
O1 S1 N1 106.08(10)
O2 S1 N1 112.23(10)
O1 S1 C1 107.02(11)
O2 S1 C1 107.82(11)
N1 S1 C1 105.36(10)
O3 S2 O4 116.77(10)
O3 S2 N1 105.20(10)
O4 S2 N1 113.24(9)
O3 S2 C2 106.96(11)
O4 S2 C2 107.72(10)
N1 S2 C2 106.33(10)
O16 C11 C12 108.73(17)
O11 C12 C11 108.96(17)
O11 C13 C14 108.93(17)
O12 C14 C13 109.28(17)
O12 C15 C16 109.25(17)
O13 C16 C15 108.86(17)
O13 C17 C18 109.25(17)
O14 C18 C17 109.23(17)
O14 C19 C20 107.76(19)
O15 C20 C19 108.14(18)
O15 C21 C22 108.76(18)
O16 C22 C21 109.57(17)
C12 O11 C13 112.55(16)
C15 O12 C14 111.49(16)
C17 O13 C16 111.15(15)
C19 O14 C18 111.86(16)
C20 O15 C21 113.53(16)
C11 O16 C22 111.60(16)
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
N1 S2 . 1.5995(18) ?
N1 S1 . 1.6149(18) ?
S1 O1 . 1.4374(16) ?
S1 O2 . 1.4413(16) ?
S1 C1 . 1.757(2) ?
S2 O3 . 1.4405(16) ?
S2 O4 . 1.4452(16) ?
S2 C2 . 1.760(2) ?
C11 O16 . 1.420(2) ?
C11 C12 . 1.498(3) ?
C12 O11 . 1.426(2) ?
C13 O11 . 1.428(3) ?
C13 C14 . 1.489(3) ?
C14 O12 . 1.425(2) ?
C15 O12 . 1.423(2) ?
C15 C16 . 1.493(3) ?
C16 O13 . 1.428(2) ?
C17 O13 . 1.428(2) ?
C17 C18 . 1.493(3) ?
C18 O14 . 1.424(2) ?
C19 O14 . 1.422(3) ?
C19 C20 . 1.495(3) ?
C20 O15 . 1.420(2) ?
C21 O15 . 1.422(2) ?
C21 C22 . 1.500(3) ?
C22 O16 . 1.424(2) ?
N2 O5 . 1.410(2) ?
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
O5 H01 N1 . 0.93(3) 1.76(3) 2.677(2) 171(3) y
N2 H02 O11 . 0.912(18) 1.972(19) 2.876(2) 171(3) y
N2 H03 O13 . 0.919(18) 2.05(2) 2.930(2) 160(3) y
N2 H04 O15 . 0.924(19) 2.11(2) 2.911(2) 144(3) y
C22 H22B O16 8_765 0.99 2.52 3.282(3) 134.0 y
C17 H17B O1 5_656 0.99 2.66 3.403(3) 132.0 ?
C14 H14B O3 3_645 0.99 2.68 3.528(3) 143.7 ?
C15 H15B O3 . 0.99 2.56 3.395(3) 142.2 y
C1 H1B O4 8_665 0.98 2.74 3.318(3) 118.0 ?
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
S2 N1 S1 O1 167.05(12)
S2 N1 S1 O2 37.40(15)
S2 N1 S1 C1 -79.68(14)
S1 N1 S2 O3 170.28(12)
S1 N1 S2 O4 41.62(15)
S1 N1 S2 C2 -76.48(14)
O16 C11 C12 O11 63.7(2)
O11 C13 C14 O12 -64.4(2)
O12 C15 C16 O13 63.9(2)
O13 C17 C18 O14 -69.8(2)
O14 C19 C20 O15 62.9(2)
O15 C21 C22 O16 -65.5(2)
C11 C12 O11 C13 -172.67(17)
C14 C13 O11 C12 -174.09(16)
C16 C15 O12 C14 -178.83(17)
C13 C14 O12 C15 -177.06(18)
C18 C17 O13 C16 176.23(18)
C15 C16 O13 C17 -179.32(17)
C20 C19 O14 C18 176.93(18)
C17 C18 O14 C19 -176.27(18)
C19 C20 O15 C21 -176.69(19)
C22 C21 O15 C20 -169.74(18)
C12 C11 O16 C22 170.56(17)
C21 C22 O16 C11 172.50(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652229
