#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/49/2014932.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_2014932
loop_
_publ_author_name
'Dale, Sophie H.'
'Elsegood, Mark R. J.'
'Gilby, Liam M.'
'Holmes, Kathryn E.'
'Kelly, Paul F.'
_publ_section_title
;1λ⁴,4λ⁴,8λ⁴,11λ⁴-Tetrathiacyclotetradecane-1,4,7,10-tetraylidenetetraaminium
 tetrakis(2,4,6-trimethylbenzenesulfonate)
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o411
_journal_page_last               o413
_journal_paper_doi               10.1107/S010827010501437X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C10 H28 N4 S4 4+ , 4C9 H11 O3 S -'
_chemical_formula_moiety         'C10 H28 N4 S4 4+ , 4C9 H11 O3 S -'
_chemical_formula_sum            'C46 H72 N4 O12 S8'
_chemical_formula_weight         1129.56
_chemical_name_systematic
;
1λ⁴,4λ⁴,8λ⁴,11λ⁴-Tetrathiacyclotetradecane-1,4,7,10-
tetraylidenetetraaminium tetrakis(2,4,6-trimethylbenzenesulfonate)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens
'Geom except NH coords refined with restraints'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                98.540(4)
_cell_angle_beta                 104.135(4)
_cell_angle_gamma                99.119(4)
_cell_formula_units_Z            1
_cell_length_a                   8.750(2)
_cell_length_b                   11.566(3)
_cell_length_c                   14.383(4)
_cell_measurement_reflns_used    1398
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.65
_cell_measurement_theta_min      2.45
_cell_volume                     1366.8(6)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2000)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_sigmaI/netI    0.1574
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10556
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.82
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.562
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2000)'
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         5312
_refine_ls_number_restraints     226
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1941
_refine_ls_R_factor_gt           0.0770
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0916P)²+1.6284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1739
_refine_ls_wR_factor_ref         0.2325
_reflns_number_gt                2257
_reflns_number_total             5312
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sq1209.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_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 (9 times).

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

The following automatic conversions were performed:

'_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 (9 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2014932
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C1 0.7133(10) 0.0279(6) 0.3117(6) 0.057(2) Uani d D 1 . . C
H1C 0.7337 0.0346 0.2478 0.069 Uiso calc PR 0.595(7) A 1 H
H1D 0.8179 0.0322 0.3594 0.069 Uiso calc PR 0.595(7) A 1 H
H1E 0.8136 0.0599 0.2958 0.069 Uiso d PR 0.405(7) A 2 H
H1F 0.6373 -0.0210 0.2507 0.069 Uiso d PR 0.405(7) A 2 H
C2 0.6388(8) 0.1342(6) 0.3456(4) 0.048(2) Uani d D 1 . . C
H2E 0.5200 0.1094 0.3252 0.058 Uiso calc R 1 . . H
H2F 0.6685 0.2009 0.3134 0.058 Uiso calc R 1 . . H
S1 0.7055(2) 0.18456(17) 0.47483(14) 0.0435(5) Uani d D 1 A . S
N1 0.8901(7) 0.2658(6) 0.4919(5) 0.0516(17) Uani d D 1 . . N
H1A 0.947(8) 0.275(6) 0.554(2) 0.062 Uiso d D 1 . . H
H1B 0.881(9) 0.334(4) 0.471(5) 0.062 Uiso d D 1 . . H
C3 0.5712(8) 0.2795(6) 0.4981(5) 0.049(2) Uani d D 1 . . C
H3A 0.6210 0.3636 0.5015 0.059 Uiso calc PR 0.595(7) A 1 H
H3B 0.4701 0.2578 0.4444 0.059 Uiso calc PR 0.595(7) A 1 H
H3C 0.6210 0.3325 0.5628 0.059 Uiso d PR 0.405(7) A 2 H
H3D 0.5583 0.3306 0.4484 0.059 Uiso d PR 0.405(7) A 2 H
S2 0.4231(3) 0.11895(18) 0.58369(15) 0.0527(6) Uani d D 1 . . S
N2 0.2396(10) 0.1364(11) 0.5195(7) 0.054(3) Uani d PD 0.595(7) A 1 N
H2A 0.180(12) 0.062(4) 0.506(10) 0.065 Uiso d PD 0.595(7) A 1 H
H2B 0.184(11) 0.193(6) 0.532(9) 0.065 Uiso d PD 0.595(7) A 1 H
C4 0.5343(14) 0.2650(6) 0.5966(7) 0.048(4) Uani d PD 0.595(7) A 1 C
H4A 0.4715 0.3245 0.6146 0.057 Uiso calc PR 0.595(7) A 1 H
H4B 0.6361 0.2786 0.6490 0.057 Uiso calc PR 0.595(7) A 1 H
C5 0.3976(14) 0.0945(9) 0.6982(5) 0.042(3) Uani d PD 0.595(7) . 1 C
H5A 0.5040 0.0976 0.7436 0.050 Uiso calc PR 0.595(7) A 1 H
H5B 0.3503 0.1589 0.7264 0.050 Uiso calc PR 0.595(7) A 1 H
N2X 0.5212(16) 0.2155(12) 0.6912(8) 0.049(5) Uani d PD 0.405(7) A 2 N
H2C 0.620(9) 0.218(13) 0.730(11) 0.059 Uiso d PD 0.405(7) A 2 H
H2D 0.493(17) 0.288(7) 0.699(12) 0.059 Uiso d PD 0.405(7) A 2 H
C4X 0.4028(13) 0.2138(12) 0.4974(10) 0.041(5) Uani d PD 0.405(7) A 2 C
H4C 0.3463 0.1661 0.4313 0.050 Uiso calc PR 0.405(7) A 2 H
H4D 0.3381 0.2727 0.5140 0.050 Uiso calc PR 0.405(7) A 2 H
C5X 0.2472(11) 0.0551(14) 0.6128(11) 0.049(5) Uani d PD 0.405(7) . 2 C
H5C 0.1994 0.1195 0.6405 0.059 Uiso calc PR 0.405(7) A 2 H
H5D 0.1673 0.0081 0.5524 0.059 Uiso calc PR 0.405(7) A 2 H
C6 -0.0061(8) -0.0571(6) 0.1903(5) 0.0319(16) Uani d . 1 B . C
C7 -0.1353(8) -0.1522(6) 0.1302(5) 0.0362(17) Uani d . 1 . . C
C8 -0.2400(8) -0.1258(6) 0.0485(5) 0.0391(18) Uani d . 1 . . C
H8 -0.3232 -0.1885 0.0072 0.047 Uiso calc R 1 . . H
C9 -0.2286(8) -0.0152(6) 0.0252(5) 0.0370(17) Uani d . 1 . . C
C10 -0.1067(8) 0.0772(7) 0.0859(5) 0.0417(18) Uani d . 1 . . C
H10 -0.0979 0.1549 0.0712 0.050 Uiso calc R 1 . . H
C11 0.0027(8) 0.0578(6) 0.1681(5) 0.0390(17) Uani d . 1 . . C
C12 -0.1674(9) -0.2770(6) 0.1504(6) 0.0466(19) Uani d . 1 . . C
H12A -0.2693 -0.3224 0.1052 0.070 Uiso calc R 1 . . H
H12B -0.1739 -0.2728 0.2179 0.070 Uiso calc R 1 . . H
H12C -0.0797 -0.3167 0.1413 0.070 Uiso calc R 1 . . H
C13 -0.3466(9) 0.0080(7) -0.0648(5) 0.051(2) Uani d . 1 . . C
H13A -0.2895 0.0249 -0.1135 0.076 Uiso calc R 1 . . H
H13B -0.3927 0.0766 -0.0455 0.076 Uiso calc R 1 . . H
H13C -0.4330 -0.0627 -0.0929 0.076 Uiso calc R 1 . . H
C14 0.1262(9) 0.1682(7) 0.2307(7) 0.061(2) Uani d . 1 . . C
H14A 0.1189 0.1780 0.2983 0.092 Uiso calc R 1 . . H
H14B 0.1039 0.2392 0.2045 0.092 Uiso calc R 1 . . H
H14C 0.2348 0.1580 0.2294 0.092 Uiso calc R 1 . . H
S3 0.1282(2) -0.08465(16) 0.29527(12) 0.0377(5) Uani d DU 1 . . S
O1 0.1551(16) -0.2038(6) 0.2688(10) 0.052(2) Uani d PDU 0.72(3) B 1 O
O2 0.0467(13) -0.0767(16) 0.3716(6) 0.046(2) Uani d PDU 0.72(3) B 1 O
O3 0.2758(9) 0.0034(9) 0.3207(10) 0.047(2) Uani d PDU 0.72(3) B 1 O
O1X 0.120(4) -0.2100(7) 0.292(2) 0.044(4) Uani d PDU 0.28(3) B 2 O
O2X 0.080(4) -0.028(3) 0.3762(14) 0.047(3) Uani d PDU 0.28(3) B 2 O
O3X 0.2844(18) -0.023(3) 0.295(2) 0.043(3) Uani d PDU 0.28(3) B 2 O
C15 0.7477(10) 0.4595(6) 0.2276(6) 0.0464(19) Uani d . 1 A . C
C16 0.9016(9) 0.4532(6) 0.2148(5) 0.0435(19) Uani d . 1 . . C
C17 0.9139(9) 0.4111(6) 0.1211(6) 0.0468(19) Uani d . 1 . . C
H17 1.0172 0.4058 0.1127 0.056 Uiso calc R 1 . . H
C18 0.7806(10) 0.3767(6) 0.0397(6) 0.0464(19) Uani d . 1 . . C
C19 0.6291(9) 0.3873(6) 0.0536(5) 0.0439(19) Uani d . 1 . . C
H19 0.5371 0.3661 -0.0014 0.053 Uiso calc R 1 . . H
C20 0.6099(9) 0.4274(6) 0.1449(5) 0.0420(18) Uani d . 1 . . C
C21 1.0584(10) 0.4939(8) 0.2960(7) 0.068(3) Uani d . 1 . . C
H21A 1.1460 0.4675 0.2728 0.102 Uiso calc R 1 . . H
H21B 1.0478 0.4591 0.3528 0.102 Uiso calc R 1 . . H
H21C 1.0825 0.5812 0.3146 0.102 Uiso calc R 1 . . H
C22 0.7969(11) 0.3339(8) -0.0612(6) 0.060(2) Uani d . 1 . . C
H22A 0.8307 0.4029 -0.0890 0.091 Uiso calc R 1 . . H
H22B 0.6931 0.2875 -0.1033 0.091 Uiso calc R 1 . . H
H22C 0.8777 0.2836 -0.0568 0.091 Uiso calc R 1 . . H
C23 0.4402(10) 0.4354(8) 0.1492(6) 0.062(2) Uani d . 1 . . C
H23A 0.3669 0.4121 0.0831 0.093 Uiso calc R 1 . . H
H23B 0.4380 0.5175 0.1771 0.093 Uiso calc R 1 . . H
H23C 0.4062 0.3816 0.1903 0.093 Uiso calc R 1 . . H
S4 0.7326(3) 0.52036(18) 0.34695(14) 0.0540(6) Uani d DU 1 . . S
O4 0.7774(13) 0.6468(4) 0.3568(10) 0.043(2) Uani d PDU 0.595(7) A 1 O
O5 0.8581(11) 0.4817(9) 0.4147(7) 0.070(2) Uani d PDU 0.595(7) A 1 O
O6 0.5787(8) 0.4714(11) 0.3578(8) 0.076(3) Uani d PDU 0.595(7) A 1 O
O4X 0.8243(16) 0.6401(6) 0.3776(15) 0.035(3) Uani d PDU 0.405(7) A 2 O
O5X 0.768(2) 0.4351(11) 0.4073(10) 0.069(3) Uani d PDU 0.405(7) A 2 O
O6X 0.5648(8) 0.5275(13) 0.3348(11) 0.064(3) Uani d PDU 0.405(7) A 2 O
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C5 C1 C2 2_656 . 112.3(7)
C2 C1 C5X . 2_656 115.3(8)
C5 C1 H1C 2_656 . 109.1
C2 C1 H1C . . 109.1
C5X C1 H1C 2_656 . 135.2
C5 C1 H1D 2_656 . 109.1
C2 C1 H1D . . 109.1
C5X C1 H1D 2_656 . 52.7
H1C C1 H1D . . 107.9
C5 C1 H1E 2_656 . 138.7
C2 C1 H1E . . 108.5
C5X C1 H1E 2_656 . 108.5
H1C C1 H1E . . 49.6
H1D C1 H1E . . 61.2
C5 C1 H1F 2_656 . 53.8
C2 C1 H1F . . 108.1
C5X C1 H1F 2_656 . 108.6
H1C C1 H1F . . 60.0
H1D C1 H1F . . 142.7
H1E C1 H1F . . 107.5
C1 C2 S1 . . 112.0(5)
C1 C2 H2E . . 109.2
S1 C2 H2E . . 109.2
C1 C2 H2F . . 109.2
S1 C2 H2F . . 109.2
H2E C2 H2F . . 107.9
N1 S1 C2 . . 102.8(4)
N1 S1 C3 . . 110.3(4)
C2 S1 C3 . . 103.4(3)
S1 N1 H1A . . 110(5)
S1 N1 H1B . . 109(5)
H1A N1 H1B . . 115(6)
C4X C3 S1 . . 115.0(7)
C4 C3 S1 . . 109.0(6)
C4X C3 H3A . . 134.7
C4 C3 H3A . . 109.9
S1 C3 H3A . . 109.9
C4X C3 H3B . . 50.6
C4 C3 H3B . . 109.9
S1 C3 H3B . . 109.9
H3A C3 H3B . . 108.3
C4X C3 H3C . . 108.3
C4 C3 H3C . . 52.6
S1 C3 H3C . . 108.5
H3A C3 H3C . . 60.7
H3B C3 H3C . . 141.5
C4X C3 H3D . . 108.6
C4 C3 H3D . . 141.6
S1 C3 H3D . . 108.6
H3A C3 H3D . . 48.9
H3B C3 H3D . . 62.9
H3C C3 H3D . . 107.6
N2X S2 C5X . . 100.2(8)
N2 S2 C4 . . 99.1(6)
N2X S2 C4X . . 103.1(8)
C5X S2 C4X . . 117.8(6)
N2 S2 C5 . . 104.9(6)
C4 S2 C5 . . 110.0(5)
S2 N2 H2A . . 102(8)
S2 N2 H2B . . 129(8)
H2A N2 H2B . . 113(7)
C3 C4 S2 . . 109.0(5)
C3 C4 H4A . . 109.9
S2 C4 H4A . . 109.9
C3 C4 H4B . . 109.9
S2 C4 H4B . . 109.9
H4A C4 H4B . . 108.3
C1 C5 S2 2_656 . 111.6(6)
C1 C5 H5A 2_656 . 109.3
S2 C5 H5A . . 109.3
C1 C5 H5B 2_656 . 109.3
S2 C5 H5B . . 109.3
H5A C5 H5B . . 108.0
S2 N2X H2C . . 128(10)
S2 N2X H2D . . 116(10)
H2C N2X H2D . . 111(7)
C3 C4X S2 . . 109.4(6)
C3 C4X H4C . . 109.8
S2 C4X H4C . . 109.8
C3 C4X H4D . . 109.8
S2 C4X H4D . . 109.8
H4C C4X H4D . . 108.2
C1 C5X S2 2_656 . 110.9(6)
C1 C5X H5C 2_656 . 109.5
S2 C5X H5C . . 109.5
C1 C5X H5D 2_656 . 109.5
S2 C5X H5D . . 109.5
H5C C5X H5D . . 108.0
C11 C6 C7 . . 118.8(6)
C11 C6 S3 . . 121.6(5)
C7 C6 S3 . . 119.5(5)
C8 C7 C6 . . 117.5(6)
C8 C7 C12 . . 118.1(6)
C6 C7 C12 . . 124.4(6)
C9 C8 C7 . . 123.7(7)
C9 C8 H8 . . 118.1
C7 C8 H8 . . 118.1
C8 C9 C10 . . 118.2(6)
C8 C9 C13 . . 121.3(7)
C10 C9 C13 . . 120.5(6)
C9 C10 C11 . . 121.5(7)
C9 C10 H10 . . 119.3
C11 C10 H10 . . 119.3
C10 C11 C6 . . 120.2(7)
C10 C11 C14 . . 116.0(6)
C6 C11 C14 . . 123.8(6)
C7 C12 H12A . . 109.5
C7 C12 H12B . . 109.5
H12A C12 H12B . . 109.5
C7 C12 H12C . . 109.5
H12A C12 H12C . . 109.5
H12B C12 H12C . . 109.5
C9 C13 H13A . . 109.5
C9 C13 H13B . . 109.5
H13A C13 H13B . . 109.5
C9 C13 H13C . . 109.5
H13A C13 H13C . . 109.5
H13B C13 H13C . . 109.5
C11 C14 H14A . . 109.5
C11 C14 H14B . . 109.5
H14A C14 H14B . . 109.5
C11 C14 H14C . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
O1X S3 O3X . . 112.3(10)
O1X S3 O2X . . 112.6(9)
O3X S3 O2X . . 110.4(9)
O3 S3 O1 . . 111.5(5)
O3 S3 O2 . . 112.0(4)
O1 S3 O2 . . 111.6(5)
O1X S3 C6 . . 111.7(13)
O3X S3 C6 . . 104.8(13)
O2X S3 C6 . . 104.3(11)
O3 S3 C6 . . 108.8(5)
O1 S3 C6 . . 106.4(5)
O2 S3 C6 . . 106.2(5)
C16 C15 C20 . . 119.7(7)
C16 C15 S4 . . 118.9(6)
C20 C15 S4 . . 121.2(6)
C17 C16 C15 . . 118.8(7)
C17 C16 C21 . . 116.7(7)
C15 C16 C21 . . 124.4(7)
C18 C17 C16 . . 122.4(7)
C18 C17 H17 . . 118.8
C16 C17 H17 . . 118.8
C17 C18 C19 . . 117.8(7)
C17 C18 C22 . . 121.6(7)
C19 C18 C22 . . 120.6(7)
C20 C19 C18 . . 122.1(7)
C20 C19 H19 . . 118.9
C18 C19 H19 . . 118.9
C19 C20 C15 . . 119.1(7)
C19 C20 C23 . . 116.6(7)
C15 C20 C23 . . 124.3(7)
C16 C21 H21A . . 109.5
C16 C21 H21B . . 109.5
H21A C21 H21B . . 109.5
C16 C21 H21C . . 109.5
H21A C21 H21C . . 109.5
H21B C21 H21C . . 109.5
C18 C22 H22A . . 109.5
C18 C22 H22B . . 109.5
H22A C22 H22B . . 109.5
C18 C22 H22C . . 109.5
H22A C22 H22C . . 109.5
H22B C22 H22C . . 109.5
C20 C23 H23A . . 109.5
C20 C23 H23B . . 109.5
H23A C23 H23B . . 109.5
C20 C23 H23C . . 109.5
H23A C23 H23C . . 109.5
H23B C23 H23C . . 109.5
O4 S4 O6 . . 118.6(7)
O5X S4 O4X . . 119.0(8)
O5X S4 O6X . . 107.9(7)
O4X S4 O6X . . 106.9(7)
O4 S4 O5 . . 108.1(6)
O6 S4 O5 . . 109.6(6)
O5X S4 C15 . . 107.1(7)
O4 S4 C15 . . 104.9(6)
O6 S4 C15 . . 110.1(5)
O4X S4 C15 . . 109.1(10)
O6X S4 C15 . . 106.1(7)
O5 S4 C15 . . 104.7(5)
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
C1 C5 2_656 1.550(8) y
C1 C2 . 1.551(7) y
C1 C5X 2_656 1.566(9) ?
C1 H1C . 0.9900 ?
C1 H1D . 0.9900 ?
C1 H1E . 0.9900 ?
C1 H1F . 0.9900 ?
C2 H2E . 0.9900 ?
C2 H2F . 0.9900 ?
C3 C4X . 1.544(9) ?
C3 C4 . 1.554(9) y
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C3 H3C . 0.9900 ?
C3 H3D . 0.9900 ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
S1 N1 . 1.676(6) y
S1 C2 . 1.782(5) y
S1 C3 . 1.786(5) y
N1 H1A . 0.89(2) ?
N1 H1B . 0.90(2) ?
S2 N2 . 1.705(6) y
S2 N2X . 1.706(7) ?
S2 C5X . 1.770(6) ?
S2 C4 . 1.770(6) y
S2 C4X . 1.771(6) ?
S2 C5 . 1.772(5) y
N2 H2A . 0.90(2) ?
N2 H2B . 0.89(2) ?
N2X H2C . 0.903(15) ?
N2X H2D . 0.91(2) ?
C4X H4C . 0.9900 ?
C4X H4D . 0.9900 ?
C5X H5C . 0.9900 ?
C5X H5D . 0.9900 ?
C6 C11 . 1.406(9) ?
C6 C7 . 1.443(9) ?
C6 S3 . 1.777(7) ?
C7 C8 . 1.409(9) ?
C7 C12 . 1.510(10) ?
C8 C9 . 1.364(9) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.396(9) ?
C9 C13 . 1.534(9) ?
C10 C11 . 1.400(9) ?
C10 H10 . 0.9500 ?
C11 C14 . 1.535(10) ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
S3 O1X . 1.434(4) ?
S3 O3X . 1.437(4) ?
S3 O2X . 1.439(4) ?
S3 O3 . 1.442(4) ?
S3 O1 . 1.445(4) ?
S3 O2 . 1.448(4) ?
C15 C16 . 1.414(10) ?
C15 C20 . 1.425(10) ?
C15 S4 . 1.801(8) ?
C16 C17 . 1.399(10) ?
C16 C21 . 1.523(10) ?
C17 C18 . 1.392(10) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.410(10) ?
C18 C22 . 1.511(10) ?
C19 C20 . 1.385(10) ?
C19 H19 . 0.9500 ?
C20 C23 . 1.518(10) ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
C22 H22A . 0.9800 ?
C22 H22B . 0.9800 ?
C22 H22C . 0.9800 ?
C23 H23A . 0.9800 ?
C23 H23B . 0.9800 ?
C23 H23C . 0.9800 ?
S4 O5X . 1.429(4) ?
S4 O4 . 1.429(4) ?
S4 O6 . 1.430(4) ?
S4 O4X . 1.431(4) ?
S4 O6X . 1.453(5) ?
S4 O5 . 1.455(4) ?
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
N1 H1A O4 2_766 0.89(2) 2.40(6) 3.090(12) 135(6)
N1 H1A O4X 2_766 0.89(2) 2.02(6) 2.683(12) 130(6)
N1 H1B O5 . 0.90(2) 2.01(2) 2.905(11) 177(7)
N1 H1B O5X . 0.90(2) 1.85(4) 2.681(9) 154(7)
N2 H2A O2 . 0.90(2) 2.25(10) 2.969(19) 136(12)
N2 H2B O4 2_666 0.89(2) 2.19(8) 2.897(15) 136(10)
N2X H2C O1X 2_656 0.903(15) 2.39(13) 3.10(4) 136(15)
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_1
_geom_torsion_site_symmetry_4
_geom_torsion
C5 C1 C2 S1 2_656 . 94.3(7)
C5X C1 C2 S1 2_656 . 30.1(9)
C1 C2 S1 N1 . . 78.3(6)
C1 C2 S1 C3 . . -166.9(5)
N1 S1 C3 C4X . . -172.7(6)
C2 S1 C3 C4X . . 78.0(7)
N1 S1 C3 C4 . . -107.1(6)
C2 S1 C3 C4 . . 143.6(5)
S1 C3 C4 S2 . . -66.8(8)
N2 S2 C4 C3 . . -76.6(8)
C5 S2 C4 C3 . . 173.8(7)
N2 S2 C5 C1 . 2_656 68.8(8)
C4 S2 C5 C1 . 2_656 174.5(7)
S1 C3 C4X S2 . . 56.7(11)
N2X S2 C4X C3 . . 59.5(11)
C5X S2 C4X C3 . . 168.6(9)
N2X S2 C5X C1 . 2_656 -70.4(11)
C4X S2 C5X C1 . 2_656 178.8(9)
C11 C6 C7 C8 . . 3.9(9)
S3 C6 C7 C8 . . 179.2(5)
C11 C6 C7 C12 . . -174.8(6)
S3 C6 C7 C12 . . 0.5(9)
C6 C7 C8 C9 . . -2.1(10)
C12 C7 C8 C9 . . 176.7(6)
C7 C8 C9 C10 . . -0.2(10)
C7 C8 C9 C13 . . -179.8(7)
C8 C9 C10 C11 . . 0.7(10)
C13 C9 C10 C11 . . -179.7(7)
C9 C10 C11 C6 . . 1.2(11)
C9 C10 C11 C14 . . -177.6(7)
C7 C6 C11 C10 . . -3.6(10)
S3 C6 C11 C10 . . -178.8(5)
C7 C6 C11 C14 . . 175.2(7)
S3 C6 C11 C14 . . 0.0(10)
C11 C6 S3 O1X . . -167.6(16)
C7 C6 S3 O1X . . 17.3(16)
C11 C6 S3 O3X . . -45.6(15)
C7 C6 S3 O3X . . 139.2(15)
C11 C6 S3 O2X . . 70.5(17)
C7 C6 S3 O2X . . -104.7(17)
C11 C6 S3 O3 . . -26.4(9)
C7 C6 S3 O3 . . 158.4(8)
C11 C6 S3 O1 . . -146.7(9)
C7 C6 S3 O1 . . 38.1(9)
C11 C6 S3 O2 . . 94.4(9)
C7 C6 S3 O2 . . -80.8(9)
C20 C15 C16 C17 . . -2.4(10)
S4 C15 C16 C17 . . -177.1(6)
C20 C15 C16 C21 . . 175.2(7)
S4 C15 C16 C21 . . 0.6(10)
C15 C16 C17 C18 . . 1.0(11)
C21 C16 C17 C18 . . -176.8(7)
C16 C17 C18 C19 . . 1.0(11)
C16 C17 C18 C22 . . 178.7(7)
C17 C18 C19 C20 . . -1.6(11)
C22 C18 C19 C20 . . -179.3(7)
C18 C19 C20 C15 . . 0.1(11)
C18 C19 C20 C23 . . 179.5(7)
C16 C15 C20 C19 . . 1.9(11)
S4 C15 C20 C19 . . 176.4(5)
C16 C15 C20 C23 . . -177.4(7)
S4 C15 C20 C23 . . -2.9(10)
C16 C15 S4 O5X . . -71.2(9)
C20 C15 S4 O5X . . 114.2(9)
C16 C15 S4 O4 . . 78.1(7)
C20 C15 S4 O4 . . -96.4(7)
C16 C15 S4 O6 . . -153.3(7)
C20 C15 S4 O6 . . 32.2(9)
C16 C15 S4 O4X . . 58.8(8)
C20 C15 S4 O4X . . -115.7(8)
C16 C15 S4 O6X . . 173.7(8)
C20 C15 S4 O6X . . -0.8(9)
C16 C15 S4 O5 . . -35.5(8)
C20 C15 S4 O5 . . 149.9(7)
