#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/09/2220950.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_2220950
loop_
_publ_author_name
'Abdul Rahman, Mohd Basyaruddin'
'Omar, Emmy Maryati'
'Ng, Shie Ling'
'Kia, Reza'
'Fun, Hoong-Kun'
_publ_section_title
;
 1H,3H-Imidazolium
 (R,S)-camphor-10-sulfonate
;
_journal_coeditor_code           WW2136
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o224
_journal_page_last               o225
_journal_paper_doi               10.1107/S1600536808043742
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C3 H5 N2 +, C10 H15 O4 S -'
_chemical_formula_moiety         'C3 H5 N2 +, C10 H15 O4 S -'
_chemical_formula_sum            'C13 H20 N2 O4 S'
_chemical_formula_weight         300.37
_chemical_name_systematic
;
1H,3H-Imidazolium (2R,5S)-camphor-10-sulfonate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 90.7570(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1362(2)
_cell_length_b                   12.0126(2)
_cell_length_c                   13.2526(3)
_cell_measurement_reflns_used    9809
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      38.93
_cell_measurement_theta_min      2.29
_cell_volume                     1454.34(5)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and 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_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25973
_diffrn_reflns_theta_full        32.50
_diffrn_reflns_theta_max         32.50
_diffrn_reflns_theta_min         1.54
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.9561
_exptl_absorpt_correction_T_min  0.8995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.339
_refine_ls_abs_structure_details 'Flack (1983), 4199 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         9954
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0470P)²+0.3247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0826
_reflns_number_gt                9652
_reflns_number_total             9954
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww2136.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

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

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2220950
_cod_database_fobs_code          2220950
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1A 1.27663(3) 0.30766(2) -0.033021(19) 0.01112(5) Uani d . 1 . .
O O1A 1.29170(10) 0.19188(8) 0.00012(7) 0.01629(16) Uani d . 1 . .
O O2A 1.37452(10) 0.38323(9) 0.02074(7) 0.01975(18) Uani d . 1 . .
O O3A 1.28934(9) 0.31774(8) -0.14282(6) 0.01632(16) Uani d . 1 . .
O O4A 1.17524(10) 0.29350(10) 0.20717(7) 0.0227(2) Uani d . 1 . .
C C1A 1.09258(13) 0.35344(13) -0.00674(10) 0.0230(3) Uani d . 1 . .
H H1AA 1.0990 0.4290 0.0189 0.028 Uiso calc R 1 . .
H H1AB 1.0396 0.3569 -0.0706 0.028 Uiso calc R 1 . .
C C2A 1.00007(12) 0.28760(11) 0.06562(9) 0.0161(2) Uani d . 1 A .
C C3A 1.05299(13) 0.27735(10) 0.17433(9) 0.0146(2) Uani d . 1 . .
C C4A 0.91989(14) 0.24497(12) 0.23603(10) 0.0206(2) Uani d . 1 . .
H H4AA 0.8990 0.3005 0.2870 0.025 Uiso calc R 1 . .
H H4AB 0.9338 0.1733 0.2684 0.025 Uiso calc R 1 . .
C C5A 0.79837(14) 0.24006(14) 0.15568(11) 0.0238(3) Uani d . 1 A .
H H5AA 0.6991 0.2465 0.1822 0.029 Uiso calc R 1 . .
C C6A 0.8249(2) 0.13498(19) 0.09277(16) 0.0449(5) Uani d . 1 . .
H H6AA 0.7441 0.1211 0.0463 0.054 Uiso calc R 1 . .
H H6AB 0.8390 0.0703 0.1356 0.054 Uiso calc R 1 . .
C C7A 0.96719(18) 0.16430(16) 0.03538(13) 0.0334(4) Uani d . 1 . .
H H7AA 0.9522 0.1576 -0.0370 0.040 Uiso calc R 1 . .
H H7AB 1.0470 0.1158 0.0560 0.040 Uiso calc R 1 . .
C C8A 0.84295(13) 0.33538(17) 0.08391(10) 0.0290(3) Uani d . 1 . .
C C9A 0.7508(3) 0.3652(4) -0.0072(2) 0.0259(7) Uiso d P 0.547(9) A 1
H H9AA 0.7369 0.3004 -0.0486 0.039 Uiso calc PR 0.547(9) A 1
H H9AB 0.7993 0.4219 -0.0452 0.039 Uiso calc PR 0.547(9) A 1
H H9AC 0.6574 0.3923 0.0143 0.039 Uiso calc PR 0.547(9) A 1
C C9C 0.7443(3) 0.3212(4) -0.0153(2) 0.0206(8) Uiso d P 0.453(9) A 2
H H9CA 0.7518 0.2461 -0.0395 0.031 Uiso calc PR 0.453(9) A 2
H H9CB 0.7775 0.3717 -0.0663 0.031 Uiso calc PR 0.453(9) A 2
H H9CC 0.6441 0.3374 0.0001 0.031 Uiso calc PR 0.453(9) A 2
C C10A 0.8557(3) 0.4563(2) 0.1473(2) 0.0172(6) Uiso d P 0.547(9) A 1
H H10A 0.9196 0.4470 0.2047 0.026 Uiso calc PR 0.547(9) A 1
H H10B 0.7604 0.4783 0.1694 0.026 Uiso calc PR 0.547(9) A 1
H H10C 0.8945 0.5127 0.1038 0.026 Uiso calc PR 0.547(9) A 1
C C10C 0.8303(4) 0.4391(3) 0.1224(3) 0.0212(8) Uiso d P 0.453(9) A 2
H H10D 0.7510 0.4773 0.0890 0.032 Uiso calc PR 0.453(9) A 2
H H10E 0.9197 0.4793 0.1123 0.032 Uiso calc PR 0.453(9) A 2
H H10F 0.8110 0.4344 0.1934 0.032 Uiso calc PR 0.453(9) A 2
N N1A 0.44499(11) 0.14307(9) 0.76374(8) 0.01573(18) Uiso d . 1 . .
H H1AC 0.3885 0.1977 0.7787 0.019 Uiso calc R 1 . .
N N2A 0.56872(12) 0.02395(9) 0.67786(8) 0.01563(18) Uani d . 1 . .
H H2AA 0.6054 -0.0114 0.6278 0.019 Uiso calc R 1 . .
C C11A 0.47931(13) 0.11135(11) 0.67088(9) 0.0155(2) Uani d . 1 . .
H H11A 0.4466 0.1445 0.6113 0.019 Uiso calc R 1 . .
C C12A 0.51470(14) 0.07405(12) 0.83219(9) 0.0176(2) Uani d . 1 . .
H H12A 0.5091 0.0780 0.9021 0.021 Uiso calc R 1 . .
C C13A 0.59299(14) -0.00070(11) 0.77835(10) 0.0177(2) Uani d . 1 . .
H H13A 0.6516 -0.0575 0.8042 0.021 Uiso calc R 1 . .
S S1B 1.29554(3) 0.33636(2) 0.532398(19) 0.01117(5) Uani d . 1 . .
O O1B 1.30840(10) 0.45125(8) 0.49628(7) 0.01658(16) Uani d . 1 . .
O O2B 1.32660(9) 0.32743(8) 0.64062(6) 0.01474(15) Uani d . 1 . .
O O3B 1.37993(10) 0.25718(8) 0.47370(7) 0.01687(17) Uani d . 1 . .
O O4B 0.95635(13) 0.47418(10) 0.40752(8) 0.0267(2) Uani d . 1 . .
C C1B 1.10979(12) 0.29462(11) 0.51462(9) 0.0165(2) Uani d . 1 . .
H H1BA 1.0902 0.2916 0.4426 0.020 Uiso calc R 1 . .
H H1BB 1.1005 0.2193 0.5402 0.020 Uiso calc R 1 . .
C C2B 0.98994(12) 0.36491(10) 0.56233(9) 0.0141(2) Uani d . 1 . .
C C3B 0.91119(14) 0.44242(11) 0.48786(10) 0.0186(2) Uani d . 1 . .
C C4B 0.76277(16) 0.46991(13) 0.53347(11) 0.0233(3) Uani d . 1 . .
H H4BA 0.6828 0.4448 0.4903 0.028 Uiso calc R 1 . .
H H4BB 0.7526 0.5491 0.5456 0.028 Uiso calc R 1 . .
C C5B 0.76907(13) 0.40436(11) 0.63263(10) 0.0185(2) Uani d . 1 . .
H H5BA 0.6734 0.3897 0.6625 0.022 Uiso calc R 1 . .
C C6B 0.87688(15) 0.46647(12) 0.70195(11) 0.0217(2) Uani d . 1 . .
H H6BA 0.8732 0.4381 0.7704 0.026 Uiso calc R 1 . .
H H6BB 0.8563 0.5457 0.7026 0.026 Uiso calc R 1 . .
C C7B 1.02824(14) 0.44215(12) 0.65360(11) 0.0199(2) Uani d . 1 . .
H H7BA 1.0933 0.4049 0.7012 0.024 Uiso calc R 1 . .
H H7BB 1.0743 0.5104 0.6311 0.024 Uiso calc R 1 . .
C C8B 0.85559(12) 0.29851(11) 0.60317(9) 0.0154(2) Uani d . 1 . .
C C9B 0.89102(17) 0.22292(13) 0.69361(11) 0.0244(3) Uani d . 1 . .
H H9BA 0.8036 0.1854 0.7143 0.037 Uiso calc R 1 . .
H H9BB 0.9285 0.2672 0.7485 0.037 Uiso calc R 1 . .
H H9BC 0.9631 0.1690 0.6746 0.037 Uiso calc R 1 . .
C C10B 0.78064(14) 0.22785(12) 0.52073(11) 0.0207(2) Uani d . 1 . .
H H10G 0.6992 0.1888 0.5490 0.031 Uiso calc R 1 . .
H H10H 0.8494 0.1752 0.4945 0.031 Uiso calc R 1 . .
H H10I 0.7465 0.2755 0.4672 0.031 Uiso calc R 1 . .
N N1B 0.42936(11) 0.12226(9) 0.17235(8) 0.01373(17) Uani d . 1 . .
H H1BC 0.3802 0.1537 0.1244 0.016 Uiso calc R 1 . .
N N2B 0.56682(11) 0.00652(9) 0.25337(9) 0.01636(19) Uani d . 1 . .
H H2BA 0.6221 -0.0496 0.2668 0.020 Uiso calc R 1 . .
C C11B 0.50552(13) 0.02832(11) 0.16403(9) 0.0153(2) Uani d . 1 . .
H H11B 0.5143 -0.0145 0.1060 0.018 Uiso calc R 1 . .
C C12B 0.44173(13) 0.16124(11) 0.27007(9) 0.0154(2) Uani d . 1 . .
H H12B 0.3992 0.2253 0.2960 0.018 Uiso calc R 1 . .
C C13B 0.52797(14) 0.08788(11) 0.32086(9) 0.0171(2) Uani d . 1 . .
H H13B 0.5556 0.0918 0.3886 0.021 Uiso calc R 1 . .
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
_geom_angle_publ_flag
O2A S1A O1A . . 113.02(6) ?
O2A S1A O3A . . 112.24(6) ?
O1A S1A O3A . . 111.57(5) ?
O2A S1A C1A . . 106.46(7) ?
O1A S1A C1A . . 108.37(6) ?
O3A S1A C1A . . 104.61(6) ?
C2A C1A S1A . . 119.53(9) ?
C2A C1A H1AA . . 107.4 ?
S1A C1A H1AA . . 107.4 ?
C2A C1A H1AB . . 107.4 ?
S1A C1A H1AB . . 107.4 ?
H1AA C1A H1AB . . 107.0 ?
C1A C2A C3A . . 118.10(11) ?
C1A C2A C7A . . 116.16(11) ?
C3A C2A C7A . . 102.95(11) ?
C1A C2A C8A . . 115.32(11) ?
C3A C2A C8A . . 99.42(9) ?
C7A C2A C8A . . 102.31(12) ?
O4A C3A C2A . . 127.55(11) ?
O4A C3A C4A . . 125.97(11) ?
C2A C3A C4A . . 106.46(10) ?
C3A C4A C5A . . 102.31(10) ?
C3A C4A H4AA . . 111.3 ?
C5A C4A H4AA . . 111.3 ?
C3A C4A H4AB . . 111.3 ?
C5A C4A H4AB . . 111.3 ?
H4AA C4A H4AB . . 109.2 ?
C4A C5A C6A . . 106.96(14) ?
C4A C5A C8A . . 101.83(11) ?
C6A C5A C8A . . 103.31(13) ?
C4A C5A H5AA . . 114.5 ?
C6A C5A H5AA . . 114.5 ?
C8A C5A H5AA . . 114.5 ?
C5A C6A C7A . . 102.63(13) ?
C5A C6A H6AA . . 111.2 ?
C7A C6A H6AA . . 111.2 ?
C5A C6A H6AB . . 111.2 ?
C7A C6A H6AB . . 111.2 ?
H6AA C6A H6AB . . 109.2 ?
C6A C7A C2A . . 104.38(13) ?
C6A C7A H7AA . . 110.9 ?
C2A C7A H7AA . . 110.9 ?
C6A C7A H7AB . . 110.9 ?
C2A C7A H7AB . . 110.9 ?
H7AA C7A H7AB . . 108.9 ?
C10C C8A C9A . . 91.9(2) ?
C10C C8A C5A . . 115.18(19) ?
C9A C8A C5A . . 121.34(19) ?
C10C C8A C2A . . 118.6(2) ?
C9A C8A C2A . . 117.82(16) ?
C5A C8A C2A . . 94.20(11) ?
C10C C8A C9C . . 111.1(2) ?
C9A C8A C9C . . 19.89(13) ?
C5A C8A C9C . . 106.14(19) ?
C2A C8A C9C . . 110.03(16) ?
C10C C8A C10A . . 11.72(18) ?
C9A C8A C10A . . 103.2(2) ?
C5A C8A C10A . . 110.47(13) ?
C2A C8A C10A . . 109.62(14) ?
C9C C8A C10A . . 122.6(2) ?
C8A C9A H9AA . . 109.5 ?
C8A C9A H9AB . . 109.5 ?
H9AA C9A H9AB . . 109.5 ?
C8A C9A H9AC . . 109.5 ?
H9AA C9A H9AC . . 109.5 ?
H9AB C9A H9AC . . 109.5 ?
C8A C9C H9CA . . 109.5 ?
C8A C9C H9CB . . 109.5 ?
H9CA C9C H9CB . . 109.5 ?
C8A C9C H9CC . . 109.5 ?
H9CA C9C H9CC . . 109.5 ?
H9CB C9C H9CC . . 109.5 ?
C8A C10A H10A . . 109.5 ?
C8A C10A H10B . . 109.5 ?
H10A C10A H10B . . 109.5 ?
C8A C10A H10C . . 109.5 ?
H10A C10A H10C . . 109.5 ?
H10B C10A H10C . . 109.5 ?
C8A C10C H10D . . 109.5 ?
C8A C10C H10E . . 109.5 ?
H10D C10C H10E . . 109.5 ?
C8A C10C H10F . . 109.5 ?
H10D C10C H10F . . 109.5 ?
H10E C10C H10F . . 109.5 ?
C11A N1A C12A . . 108.91(11) ?
C11A N1A H1AC . . 125.5 ?
C12A N1A H1AC . . 125.5 ?
C11A N2A C13A . . 109.07(11) ?
C11A N2A H2AA . . 125.5 ?
C13A N2A H2AA . . 125.5 ?
N1A C11A N2A . . 108.26(11) ?
N1A C11A H11A . . 125.9 ?
N2A C11A H11A . . 125.9 ?
C13A C12A N1A . . 107.11(11) ?
C13A C12A H12A . . 126.4 ?
N1A C12A H12A . . 126.4 ?
C12A C13A N2A . . 106.65(11) ?
C12A C13A H13A . . 126.7 ?
N2A C13A H13A . . 126.7 ?
O3B S1B O2B . . 112.27(5) ?
O3B S1B O1B . . 113.28(6) ?
O2B S1B O1B . . 111.96(5) ?
O3B S1B C1B . . 104.81(5) ?
O2B S1B C1B . . 106.33(5) ?
O1B S1B C1B . . 107.57(6) ?
C2B C1B S1B . . 118.47(8) ?
C2B C1B H1BA . . 107.7 ?
S1B C1B H1BA . . 107.7 ?
C2B C1B H1BB . . 107.7 ?
S1B C1B H1BB . . 107.7 ?
H1BA C1B H1BB . . 107.1 ?
C1B C2B C3B . . 113.79(10) ?
C1B C2B C7B . . 119.69(10) ?
C3B C2B C7B . . 103.70(10) ?
C1B C2B C8B . . 115.55(10) ?
C3B C2B C8B . . 99.72(9) ?
C7B C2B C8B . . 101.75(9) ?
O4B C3B C4B . . 126.53(13) ?
O4B C3B C2B . . 126.68(12) ?
C4B C3B C2B . . 106.78(10) ?
C3B C4B C5B . . 101.81(10) ?
C3B C4B H4BA . . 111.4 ?
C5B C4B H4BA . . 111.4 ?
C3B C4B H4BB . . 111.4 ?
C5B C4B H4BB . . 111.4 ?
H4BA C4B H4BB . . 109.3 ?
C6B C5B C4B . . 106.29(12) ?
C6B C5B C8B . . 102.98(10) ?
C4B C5B C8B . . 102.65(10) ?
C6B C5B H5BA . . 114.5 ?
C4B C5B H5BA . . 114.5 ?
C8B C5B H5BA . . 114.5 ?
C5B C6B C7B . . 103.23(10) ?
C5B C6B H6BA . . 111.1 ?
C7B C6B H6BA . . 111.1 ?
C5B C6B H6BB . . 111.1 ?
C7B C6B H6BB . . 111.1 ?
H6BA C6B H6BB . . 109.1 ?
C6B C7B C2B . . 103.83(10) ?
C6B C7B H7BA . . 111.0 ?
C2B C7B H7BA . . 111.0 ?
C6B C7B H7BB . . 111.0 ?
C2B C7B H7BB . . 111.0 ?
H7BA C7B H7BB . . 109.0 ?
C9B C8B C10B . . 108.40(11) ?
C9B C8B C5B . . 113.06(11) ?
C10B C8B C5B . . 114.08(10) ?
C9B C8B C2B . . 114.39(10) ?
C10B C8B C2B . . 112.29(10) ?
C5B C8B C2B . . 94.24(9) ?
C8B C9B H9BA . . 109.5 ?
C8B C9B H9BB . . 109.5 ?
H9BA C9B H9BB . . 109.5 ?
C8B C9B H9BC . . 109.5 ?
H9BA C9B H9BC . . 109.5 ?
H9BB C9B H9BC . . 109.5 ?
C8B C10B H10G . . 109.5 ?
C8B C10B H10H . . 109.5 ?
H10G C10B H10H . . 109.5 ?
C8B C10B H10I . . 109.5 ?
H10G C10B H10I . . 109.5 ?
H10H C10B H10I . . 109.5 ?
C11B N1B C12B . . 109.21(10) ?
C11B N1B H1BC . . 125.4 ?
C12B N1B H1BC . . 125.4 ?
C11B N2B C13B . . 109.28(11) ?
C11B N2B H2BA . . 125.4 ?
C13B N2B H2BA . . 125.4 ?
N2B C11B N1B . . 107.93(11) ?
N2B C11B H11B . . 126.0 ?
N1B C11B H11B . . 126.0 ?
C13B C12B N1B . . 106.57(11) ?
C13B C12B H12B . . 126.7 ?
N1B C12B H12B . . 126.7 ?
C12B C13B N2B . . 107.01(11) ?
C12B C13B H13B . . 126.5 ?
N2B C13B H13B . . 126.5 ?
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
S1A O2A . 1.4542(10) ?
S1A O1A . 1.4645(9) ?
S1A O3A . 1.4663(8) ?
S1A C1A . 1.8074(12) ?
O4A C3A . 1.2090(15) ?
C1A C2A . 1.5102(17) ?
C1A H1AA . 0.9700 ?
C1A H1AB . 0.9700 ?
C2A C3A . 1.5185(16) ?
C2A C7A . 1.563(2) ?
C2A C8A . 1.5678(17) ?
C3A C4A . 1.5248(17) ?
C4A C5A . 1.529(2) ?
C4A H4AA . 0.9700 ?
C4A H4AB . 0.9700 ?
C5A C6A . 1.534(2) ?
C5A C8A . 1.547(2) ?
C5A H5AA . 0.9800 ?
C6A C7A . 1.555(2) ?
C6A H6AA . 0.9700 ?
C6A H6AB . 0.9700 ?
C7A H7AA . 0.9700 ?
C7A H7AB . 0.9700 ?
C8A C10C . 1.352(5) ?
C8A C9A . 1.506(3) ?
C8A C9C . 1.594(3) ?
C8A C10A . 1.681(4) ?
C9A H9AA . 0.9600 ?
C9A H9AB . 0.9600 ?
C9A H9AC . 0.9600 ?
C9C H9CA . 0.9600 ?
C9C H9CB . 0.9600 ?
C9C H9CC . 0.9600 ?
C10A H10A . 0.9600 ?
C10A H10B . 0.9600 ?
C10A H10C . 0.9600 ?
C10C H10D . 0.9600 ?
C10C H10E . 0.9600 ?
C10C H10F . 0.9600 ?
N1A C11A . 1.3297(16) ?
N1A C12A . 1.3786(17) ?
N1A H1AC . 0.8600 ?
N2A C11A . 1.3327(16) ?
N2A C13A . 1.3793(16) ?
N2A H2AA . 0.8600 ?
C11A H11A . 0.9300 ?
C12A C13A . 1.3566(18) ?
C12A H12A . 0.9300 ?
C13A H13A . 0.9300 ?
S1B O3B . 1.4560(9) ?
S1B O2B . 1.4622(8) ?
S1B O1B . 1.4661(9) ?
S1B C1B . 1.7822(12) ?
O4B C3B . 1.2088(17) ?
C1B C2B . 1.5264(16) ?
C1B H1BA . 0.9700 ?
C1B H1BB . 0.9700 ?
C2B C3B . 1.5297(18) ?
C2B C7B . 1.5606(18) ?
C2B C8B . 1.5663(16) ?
C3B C4B . 1.5280(19) ?
C4B C5B . 1.532(2) ?
C4B H4BA . 0.9700 ?
C4B H4BB . 0.9700 ?
C5B C6B . 1.532(2) ?
C5B C8B . 1.5499(18) ?
C5B H5BA . 0.9800 ?
C6B C7B . 1.5593(18) ?
C6B H6BA . 0.9700 ?
C6B H6BB . 0.9700 ?
C7B H7BA . 0.9700 ?
C7B H7BB . 0.9700 ?
C8B C9B . 1.5347(19) ?
C8B C10B . 1.5374(18) ?
C9B H9BA . 0.9600 ?
C9B H9BB . 0.9600 ?
C9B H9BC . 0.9600 ?
C10B H10G . 0.9600 ?
C10B H10H . 0.9600 ?
C10B H10I . 0.9600 ?
N1B C11B . 1.3311(16) ?
N1B C12B . 1.3803(15) ?
N1B H1BC . 0.8600 ?
N2B C11B . 1.3291(16) ?
N2B C13B . 1.3747(17) ?
N2B H2BA . 0.8600 ?
C11B H11B . 0.9300 ?
C12B C13B . 1.3552(18) ?
C12B H12B . 0.9300 ?
C13B H13B . 0.9300 ?
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
N1A H1AC O2B 1_455 0.8600 2.4600 2.9479(14) 116.00 y
N1A H1AC O3A 1_456 0.8600 2.0000 2.8293(14) 161.00 y
N2A H2AA O1B 2_746 0.8600 1.8900 2.7235(14) 164.00 y
N1B H1BC O1A 1_455 0.8600 1.8800 2.7231(14) 165.00 y
N2B H2BA O2B 2_746 0.8600 1.9700 2.7412(14) 148.00 y
N2B H2BA O3A 2_745 0.8600 2.4300 3.0111(14) 125.00 y
C7A H7AB O1A . 0.9700 2.5300 3.0257(19) 111.00 y
C11A H11A O2B 1_455 0.9300 2.4900 2.9716(16) 113.00 y
C11A H11A O3B 1_455 0.9300 2.3500 3.2648(15) 170.00 y
C11B H11B O2A 2_745 0.9300 2.3300 3.2103(16) 159.00 y
C9A H9AC O2A 1_455 0.9600 2.5900 3.469(3) 152.00 y
C12B H12B O3B 1_455 0.9300 2.3900 2.9950(15) 122.00 y
C12B H12B O4A 1_455 0.9300 2.4900 3.0155(16) 116.00 y
C13A H13A O2A 2_746 0.9300 2.4400 3.0167(16) 120.00 y
C13A H13A O4A 2_746 0.9300 2.3900 3.2591(17) 155.00 y
C13B H13B O1B 2_746 0.9300 2.5800 3.2720(16) 131.00 y
C7B H7BA O2B . 0.9700 2.4700 3.0613(16) 119.00 y
C5A H5AA Cg1 1_555 0.9800 2.8300 3.5459(5) 131.00 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2A S1A C1A C2A . . . . -105.42(12) ?
O1A S1A C1A C2A . . . . 16.45(14) ?
O3A S1A C1A C2A . . . . 135.58(11) ?
S1A C1A C2A C3A . . . . 62.08(16) ?
S1A C1A C2A C7A . . . . -60.97(16) ?
S1A C1A C2A C8A . . . . 179.34(11) ?
C1A C2A C3A O4A . . . . -18.12(19) ?
C7A C2A C3A O4A . . . . 111.36(15) ?
C8A C2A C3A O4A . . . . -143.57(14) ?
C1A C2A C3A C4A . . . . 160.54(11) ?
C7A C2A C3A C4A . . . . -69.99(12) ?
C8A C2A C3A C4A . . . . 35.08(13) ?
O4A C3A C4A C5A . . . . 178.27(13) ?
C2A C3A C4A C5A . . . . -0.41(13) ?
C3A C4A C5A C6A . . . . 72.78(14) ?
C3A C4A C5A C8A . . . . -35.27(14) ?
C4A C5A C6A C7A . . . . -68.92(19) ?
C8A C5A C6A C7A . . . . 38.09(18) ?
C5A C6A C7A C2A . . . . -4.3(2) ?
C1A C2A C7A C6A . . . . -156.62(14) ?
C3A C2A C7A C6A . . . . 72.72(16) ?
C8A C2A C7A C6A . . . . -30.11(17) ?
C4A C5A C8A C10C . . . . -68.8(2) ?
C6A C5A C8A C10C . . . . -179.6(2) ?
C4A C5A C8A C9A . . . . -178.0(2) ?
C6A C5A C8A C9A . . . . 71.1(2) ?
C4A C5A C8A C2A . . . . 55.64(13) ?
C6A C5A C8A C2A . . . . -55.21(14) ?
C4A C5A C8A C9C . . . . 167.90(17) ?
C6A C5A C8A C9C . . . . 57.05(19) ?
C4A C5A C8A C10A . . . . -57.12(16) ?
C6A C5A C8A C10A . . . . -167.96(15) ?
C1A C2A C8A C10C . . . . -60.1(2) ?
C3A C2A C8A C10C . . . . 67.3(2) ?
C7A C2A C8A C10C . . . . 172.9(2) ?
C1A C2A C8A C9A . . . . 49.3(3) ?
C3A C2A C8A C9A . . . . 176.6(2) ?
C7A C2A C8A C9A . . . . -77.8(3) ?
C1A C2A C8A C5A . . . . 178.22(12) ?
C3A C2A C8A C5A . . . . -54.43(12) ?
C7A C2A C8A C5A . . . . 51.17(13) ?
C1A C2A C8A C9C . . . . 69.4(2) ?
C3A C2A C8A C9C . . . . -163.3(2) ?
C7A C2A C8A C9C . . . . -57.7(2) ?
C1A C2A C8A C10A . . . . -68.30(16) ?
C3A C2A C8A C10A . . . . 59.06(15) ?
C7A C2A C8A C10A . . . . 164.65(14) ?
C12A N1A C11A N2A . . . . 0.11(14) ?
C13A N2A C11A N1A . . . . -0.31(14) ?
C11A N1A C12A C13A . . . . 0.14(15) ?
N1A C12A C13A N2A . . . . -0.32(15) ?
C11A N2A C13A C12A . . . . 0.40(15) ?
O3B S1B C1B C2B . . . . -176.85(9) ?
O2B S1B C1B C2B . . . . 64.08(11) ?
O1B S1B C1B C2B . . . . -56.02(11) ?
S1B C1B C2B C3B . . . . 101.52(11) ?
S1B C1B C2B C7B . . . . -21.79(16) ?
S1B C1B C2B C8B . . . . -143.94(9) ?
C1B C2B C3B O4B . . . . -20.75(19) ?
C7B C2B C3B O4B . . . . 110.90(15) ?
C8B C2B C3B O4B . . . . -144.36(14) ?
C1B C2B C3B C4B . . . . 157.98(11) ?
C7B C2B C3B C4B . . . . -70.38(12) ?
C8B C2B C3B C4B . . . . 34.36(12) ?
O4B C3B C4B C5B . . . . 178.76(14) ?
C2B C3B C4B C5B . . . . 0.04(14) ?
C3B C4B C5B C6B . . . . 72.54(13) ?
C3B C4B C5B C8B . . . . -35.24(13) ?
C4B C5B C6B C7B . . . . -71.47(13) ?
C8B C5B C6B C7B . . . . 36.08(13) ?
C5B C6B C7B C2B . . . . -1.55(14) ?
C1B C2B C7B C6B . . . . -161.59(11) ?
C3B C2B C7B C6B . . . . 70.33(12) ?
C8B C2B C7B C6B . . . . -32.87(13) ?
C6B C5B C8B C9B . . . . 63.83(13) ?
C4B C5B C8B C9B . . . . 174.13(11) ?
C6B C5B C8B C10B . . . . -171.69(11) ?
C4B C5B C8B C10B . . . . -61.40(13) ?
C6B C5B C8B C2B . . . . -54.96(11) ?
C4B C5B C8B C2B . . . . 55.33(11) ?
C1B C2B C8B C9B . . . . 66.55(14) ?
C3B C2B C8B C9B . . . . -171.07(11) ?
C7B C2B C8B C9B . . . . -64.75(13) ?
C1B C2B C8B C10B . . . . -57.54(14) ?
C3B C2B C8B C10B . . . . 64.84(12) ?
C7B C2B C8B C10B . . . . 171.16(11) ?
C1B C2B C8B C5B . . . . -175.74(10) ?
C3B C2B C8B C5B . . . . -53.37(10) ?
C7B C2B C8B C5B . . . . 52.95(11) ?
C13B N2B C11B N1B . . . . 0.55(14) ?
C12B N1B C11B N2B . . . . -0.35(14) ?
C11B N1B C12B C13B . . . . 0.01(14) ?
N1B C12B C13B N2B . . . . 0.32(13) ?
C11B N2B C13B C12B . . . . -0.54(14) ?
