#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/23/2222380.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_2222380
loop_
_publ_author_name
'Chanawanno, Kullapa'
'Chantrapromma, Suchada'
'Fun, Hoong-Kun'
_publ_section_title
;
 2-[(E)-2-(4-Chlorophenyl)ethenyl]-1-methylpyridinium
 4-methoxybenzenesulfonate
;
_journal_coeditor_code           IS2428
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1549
_journal_page_last               o1550
_journal_paper_doi               10.1107/S1600536809021679
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H13 Cl N +, C7 H7 O4 S -'
_chemical_formula_moiety         'C14 H13 Cl N +, C7 H7 O4 S -'
_chemical_formula_sum            'C21 H20 Cl N O4 S'
_chemical_formula_weight         417.90
_chemical_melting_point_gt       476
_chemical_melting_point_lt       477
_chemical_name_systematic
;
2-[(E)-2-(4-Chlorophenyl)ethenyl]-1-methylpyridinium
4-methoxybenzenesulfonate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 99.8420(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.2323(2)
_cell_length_b                   14.2222(2)
_cell_length_c                   17.9709(3)
_cell_measurement_reflns_used    13850
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.50
_cell_measurement_theta_min      2.16
_cell_volume                     3835.86(10)
_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, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            65482
_diffrn_reflns_theta_full        32.50
_diffrn_reflns_theta_max         32.50
_diffrn_reflns_theta_min         2.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.337
_exptl_absorpt_correction_T_max  0.9206
_exptl_absorpt_correction_T_min  0.8487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.967
_refine_diff_density_min         -0.362
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         13850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0432
_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)+(0.0623P)²+1.6315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1239
_reflns_number_gt                11056
_reflns_number_total             13850
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2428.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/c'
_cod_database_code               2222380
_cod_database_fobs_code          2222380
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Cl Cl1A 0.32287(2) 0.88225(2) 0.45723(2) 0.02793(8) Uani d . 1 . .
S S1A 0.48109(2) 0.93858(2) 0.237547(19) 0.01944(7) Uani d . 1 . .
O O1A 0.23458(7) 0.61426(7) 0.18741(6) 0.0284(2) Uani d . 1 . .
O O2A 0.44566(8) 1.00518(8) 0.17884(7) 0.0341(3) Uani d . 1 . .
O O3A 0.56868(7) 0.90330(9) 0.23050(9) 0.0404(3) Uani d . 1 . .
O O4A 0.47682(7) 0.97356(8) 0.31282(6) 0.0275(2) Uani d . 1 . .
N N1A 0.39490(7) 0.25104(9) 0.56571(7) 0.0238(2) Uani d . 1 . .
C C1A 0.26165(8) 0.77407(10) 0.21133(7) 0.0209(2) Uani d . 1 . .
H H1AA 0.2012 0.7817 0.2120 0.025 Uiso calc R 1 . .
C C2A 0.31827(8) 0.85064(9) 0.22216(7) 0.0190(2) Uani d . 1 . .
H H2AA 0.2954 0.9100 0.2291 0.023 Uiso calc R 1 . .
C C3A 0.40971(8) 0.83949(9) 0.22282(7) 0.0174(2) Uani d . 1 . .
C C4A 0.44290(9) 0.75035(9) 0.21200(7) 0.0193(2) Uani d . 1 . .
H H4AA 0.5037 0.7425 0.2129 0.023 Uiso calc R 1 . .
C C5A 0.38663(9) 0.67272(9) 0.19984(7) 0.0211(2) Uani d . 1 . .
H H5AA 0.4094 0.6135 0.1921 0.025 Uiso calc R 1 . .
C C6A 0.29572(9) 0.68487(9) 0.19935(7) 0.0205(2) Uani d . 1 . .
C C7A 0.26202(13) 0.52937(11) 0.15488(9) 0.0347(4) Uani d . 1 . .
H H7AA 0.2114 0.4890 0.1408 0.052 Uiso calc R 1 . .
H H7AB 0.3058 0.4979 0.1911 0.052 Uiso calc R 1 . .
H H7AC 0.2872 0.5444 0.1109 0.052 Uiso calc R 1 . .
C C8A 0.34428(9) 0.61220(10) 0.51834(7) 0.0206(2) Uani d . 1 . .
H H8AA 0.3340 0.5758 0.5590 0.025 Uiso calc R 1 . .
C C9A 0.32870(9) 0.70814(10) 0.51876(7) 0.0212(2) Uani d . 1 . .
H H9AA 0.3075 0.7360 0.5590 0.025 Uiso calc R 1 . .
C C10A 0.34515(8) 0.76217(9) 0.45819(7) 0.0202(2) Uani d . 1 . .
C C11A 0.37708(9) 0.72212(10) 0.39728(7) 0.0214(2) Uani d . 1 . .
H H11A 0.3886 0.7593 0.3575 0.026 Uiso calc R 1 . .
C C12A 0.39139(9) 0.62607(10) 0.39716(7) 0.0210(2) Uani d . 1 . .
H H12A 0.4120 0.5987 0.3564 0.025 Uiso calc R 1 . .
C C13A 0.37542(8) 0.56894(9) 0.45724(7) 0.0187(2) Uani d . 1 . .
C C14A 0.39199(8) 0.46781(10) 0.45331(8) 0.0207(2) Uani d . 1 . .
H H14A 0.4060 0.4441 0.4086 0.025 Uiso calc R 1 . .
C C15A 0.38828(9) 0.40694(10) 0.50982(8) 0.0217(2) Uani d . 1 . .
H H15A 0.3753 0.4305 0.5550 0.026 Uiso calc R 1 . .
C C16A 0.40336(8) 0.30628(10) 0.50458(8) 0.0215(2) Uani d . 1 . .
C C17A 0.42550(9) 0.26255(11) 0.44091(9) 0.0264(3) Uani d . 1 . .
H H17A 0.4318 0.2986 0.3989 0.032 Uiso calc R 1 . .
C C18A 0.43828(10) 0.16620(11) 0.43922(11) 0.0317(3) Uani d . 1 . .
H H18A 0.4520 0.1374 0.3962 0.038 Uiso calc R 1 . .
C C19A 0.43033(10) 0.11325(11) 0.50268(11) 0.0342(4) Uani d . 1 . .
H H19A 0.4394 0.0486 0.5028 0.041 Uiso calc R 1 . .
C C20A 0.40912(10) 0.15698(11) 0.56505(10) 0.0307(3) Uani d . 1 . .
H H20A 0.4044 0.1216 0.6077 0.037 Uiso calc R 1 . .
C C21A 0.36931(11) 0.29182(11) 0.63493(9) 0.0294(3) Uani d . 1 . .
H H21A 0.3692 0.2433 0.6720 0.044 Uiso calc R 1 . .
H H21B 0.3108 0.3188 0.6228 0.044 Uiso calc R 1 . .
H H21C 0.4113 0.3397 0.6547 0.044 Uiso calc R 1 . .
Cl Cl1B 0.17518(2) 1.38107(3) 0.00463(2) 0.02803(8) Uani d . 1 . .
S S1B 1.00942(2) 0.95490(2) 0.246406(19) 0.01974(7) Uani d . 1 . .
O O1B 0.71704(7) 0.67561(7) 0.20958(6) 0.0260(2) Uani d . 1 . .
O O2B 0.98081(7) 1.02649(8) 0.18966(7) 0.0305(2) Uani d . 1 . .
O O3B 1.09004(7) 0.90609(8) 0.23490(8) 0.0344(3) Uani d . 1 . .
O O4B 1.01406(8) 0.98951(8) 0.32302(6) 0.0303(2) Uani d . 1 . .
N N1B 0.10047(8) 0.74523(10) -0.05082(8) 0.0319(3) Uani d . 1 . .
C C1B 0.76794(8) 0.83076(9) 0.22112(7) 0.0200(2) Uani d . 1 . .
H H1BA 0.7091 0.8498 0.2189 0.024 Uiso calc R 1 . .
C C2B 0.83556(8) 0.89695(9) 0.22830(7) 0.0191(2) Uani d . 1 . .
H H2BA 0.8219 0.9606 0.2298 0.023 Uiso calc R 1 . .
C C3B 0.92421(8) 0.86844(9) 0.23329(7) 0.0171(2) Uani d . 1 . .
C C4B 0.94376(8) 0.77349(9) 0.22876(7) 0.0186(2) Uani d . 1 . .
H H4BA 1.0027 0.7546 0.2316 0.022 Uiso calc R 1 . .
C C5B 0.87619(9) 0.70594(9) 0.22008(7) 0.0189(2) Uani d . 1 . .
H H5BA 0.8896 0.6425 0.2163 0.023 Uiso calc R 1 . .
C C6B 0.78849(8) 0.73524(9) 0.21724(7) 0.0190(2) Uani d . 1 . .
C C7B 0.73447(11) 0.57794(11) 0.19885(11) 0.0347(4) Uani d . 1 . .
H H7BA 0.6797 0.5432 0.1939 0.052 Uiso calc R 1 . .
H H7BB 0.7754 0.5549 0.2416 0.052 Uiso calc R 1 . .
H H7BC 0.7600 0.5703 0.1539 0.052 Uiso calc R 1 . .
C C8B 0.15924(9) 1.10411(10) -0.02634(7) 0.0228(3) Uani d . 1 . .
H H8BA 0.1699 1.0617 -0.0632 0.027 Uiso calc R 1 . .
C C9B 0.17369(9) 1.19907(10) -0.03607(7) 0.0230(3) Uani d . 1 . .
H H9BA 0.1943 1.2203 -0.0789 0.028 Uiso calc R 1 . .
C C10B 0.15711(8) 1.26222(10) 0.01867(7) 0.0202(2) Uani d . 1 . .
C C11B 0.12748(9) 1.23201(10) 0.08390(7) 0.0211(2) Uani d . 1 . .
H H11B 0.1170 1.2750 0.1204 0.025 Uiso calc R 1 . .
C C12B 0.11402(8) 1.13654(10) 0.09326(7) 0.0203(2) Uani d . 1 . .
H H12B 0.0948 1.1156 0.1368 0.024 Uiso calc R 1 . .
C C13B 0.12876(8) 1.07074(9) 0.03831(7) 0.0189(2) Uani d . 1 . .
C C14B 0.11282(8) 0.97080(10) 0.05008(7) 0.0207(2) Uani d . 1 . .
H H14B 0.1086 0.9508 0.0986 0.025 Uiso calc R 1 . .
C C15B 0.10399(9) 0.90638(10) -0.00546(8) 0.0234(3) Uani d . 1 . .
H H15B 0.1067 0.9267 -0.0542 0.028 Uiso calc R 1 . .
C C16B 0.09044(9) 0.80646(10) 0.00640(9) 0.0248(3) Uani d . 1 . .
C C17B 0.06762(9) 0.76977(10) 0.07236(9) 0.0273(3) Uani d . 1 . .
H H17B 0.0596 0.8104 0.1112 0.033 Uiso calc R 1 . .
C C18B 0.05662(10) 0.67402(11) 0.08135(12) 0.0353(4) Uani d . 1 . .
H H18B 0.0423 0.6501 0.1260 0.042 Uiso calc R 1 . .
C C19B 0.06737(11) 0.61438(12) 0.02235(13) 0.0424(5) Uani d . 1 . .
H H19B 0.0605 0.5498 0.0272 0.051 Uiso calc R 1 . .
C C20B 0.08801(11) 0.65085(13) -0.04276(12) 0.0426(5) Uani d . 1 . .
H H20B 0.0937 0.6106 -0.0825 0.051 Uiso calc R 1 . .
C C21B 0.12482(12) 0.77952(14) -0.12228(9) 0.0411(4) Uani d . 1 . .
H H21D 0.0800 0.8224 -0.1462 0.062 Uiso calc R 1 . .
H H21E 0.1290 0.7272 -0.1553 0.062 Uiso calc R 1 . .
H H21F 0.1812 0.8112 -0.1118 0.062 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3A S1A O2A . . 113.28(8) ?
O3A S1A O4A . . 112.81(8) ?
O2A S1A O4A . . 112.52(7) ?
O3A S1A C3A . . 105.18(6) ?
O2A S1A C3A . . 105.55(6) ?
O4A S1A C3A . . 106.70(6) ?
C6A O1A C7A . . 116.49(12) ?
C20A N1A C16A . . 121.34(13) ?
C20A N1A C21A . . 117.29(13) ?
C16A N1A C21A . . 121.37(12) ?
C2A C1A C6A . . 119.76(12) ?
C2A C1A H1AA . . 120.1 ?
C6A C1A H1AA . . 120.1 ?
C1A C2A C3A . . 120.53(12) ?
C1A C2A H2AA . . 119.7 ?
C3A C2A H2AA . . 119.7 ?
C4A C3A C2A . . 119.14(12) ?
C4A C3A S1A . . 121.17(9) ?
C2A C3A S1A . . 119.69(9) ?
C3A C4A C5A . . 121.08(12) ?
C3A C4A H4AA . . 119.5 ?
C5A C4A H4AA . . 119.5 ?
C4A C5A C6A . . 119.14(12) ?
C4A C5A H5AA . . 120.4 ?
C6A C5A H5AA . . 120.4 ?
O1A C6A C5A . . 124.16(12) ?
O1A C6A C1A . . 115.51(12) ?
C5A C6A C1A . . 120.32(12) ?
O1A C7A H7AA . . 109.5 ?
O1A C7A H7AB . . 109.5 ?
H7AA C7A H7AB . . 109.5 ?
O1A C7A H7AC . . 109.5 ?
H7AA C7A H7AC . . 109.5 ?
H7AB C7A H7AC . . 109.5 ?
C9A C8A C13A . . 120.99(12) ?
C9A C8A H8AA . . 119.5 ?
C13A C8A H8AA . . 119.5 ?
C8A C9A C10A . . 119.10(12) ?
C8A C9A H9AA . . 120.5 ?
C10A C9A H9AA . . 120.5 ?
C9A C10A C11A . . 121.55(13) ?
C9A C10A Cl1A . . 119.29(10) ?
C11A C10A Cl1A . . 119.15(10) ?
C12A C11A C10A . . 118.76(12) ?
C12A C11A H11A . . 120.6 ?
C10A C11A H11A . . 120.6 ?
C11A C12A C13A . . 121.45(12) ?
C11A C12A H12A . . 119.3 ?
C13A C12A H12A . . 119.3 ?
C12A C13A C8A . . 118.14(12) ?
C12A C13A C14A . . 118.49(11) ?
C8A C13A C14A . . 123.37(12) ?
C15A C14A C13A . . 124.53(12) ?
C15A C14A H14A . . 117.7 ?
C13A C14A H14A . . 117.7 ?
C14A C15A C16A . . 123.89(13) ?
C14A C15A H15A . . 118.1 ?
C16A C15A H15A . . 118.1 ?
N1A C16A C17A . . 118.05(13) ?
N1A C16A C15A . . 118.24(12) ?
C17A C16A C15A . . 123.72(13) ?
C18A C17A C16A . . 120.94(15) ?
C18A C17A H17A . . 119.5 ?
C16A C17A H17A . . 119.5 ?
C17A C18A C19A . . 119.08(16) ?
C17A C18A H18A . . 120.5 ?
C19A C18A H18A . . 120.5 ?
C20A C19A C18A . . 119.48(15) ?
C20A C19A H19A . . 120.3 ?
C18A C19A H19A . . 120.3 ?
N1A C20A C19A . . 121.09(15) ?
N1A C20A H20A . . 119.5 ?
C19A C20A H20A . . 119.5 ?
N1A C21A H21A . . 109.5 ?
N1A C21A H21B . . 109.5 ?
H21A C21A H21B . . 109.5 ?
N1A C21A H21C . . 109.5 ?
H21A C21A H21C . . 109.5 ?
H21B C21A H21C . . 109.5 ?
O4B S1B O2B . . 112.80(7) ?
O4B S1B O3B . . 113.00(7) ?
O2B S1B O3B . . 113.16(7) ?
O4B S1B C3B . . 106.07(6) ?
O2B S1B C3B . . 105.50(6) ?
O3B S1B C3B . . 105.45(6) ?
C6B O1B C7B . . 116.86(11) ?
C20B N1B C16B . . 120.48(16) ?
C20B N1B C21B . . 118.41(15) ?
C16B N1B C21B . . 121.11(15) ?
C2B C1B C6B . . 119.71(11) ?
C2B C1B H1BA . . 120.1 ?
C6B C1B H1BA . . 120.1 ?
C1B C2B C3B . . 120.24(12) ?
C1B C2B H2BA . . 119.9 ?
C3B C2B H2BA . . 119.9 ?
C4B C3B C2B . . 119.53(11) ?
C4B C3B S1B . . 121.50(9) ?
C2B C3B S1B . . 118.96(10) ?
C3B C4B C5B . . 120.94(11) ?
C3B C4B H4BA . . 119.5 ?
C5B C4B H4BA . . 119.5 ?
C6B C5B C4B . . 118.84(12) ?
C6B C5B H5BA . . 120.6 ?
C4B C5B H5BA . . 120.6 ?
O1B C6B C5B . . 124.06(12) ?
O1B C6B C1B . . 115.23(11) ?
C5B C6B C1B . . 120.70(12) ?
O1B C7B H7BA . . 109.5 ?
O1B C7B H7BB . . 109.5 ?
H7BA C7B H7BB . . 109.5 ?
O1B C7B H7BC . . 109.5 ?
H7BA C7B H7BC . . 109.5 ?
H7BB C7B H7BC . . 109.5 ?
C9B C8B C13B . . 121.06(12) ?
C9B C8B H8BA . . 119.5 ?
C13B C8B H8BA . . 119.5 ?
C8B C9B C10B . . 119.36(12) ?
C8B C9B H9BA . . 120.3 ?
C10B C9B H9BA . . 120.3 ?
C9B C10B C11B . . 121.42(13) ?
C9B C10B Cl1B . . 118.32(10) ?
C11B C10B Cl1B . . 120.26(11) ?
C12B C11B C10B . . 118.64(12) ?
C12B C11B H11B . . 120.7 ?
C10B C11B H11B . . 120.7 ?
C11B C12B C13B . . 121.42(12) ?
C11B C12B H12B . . 119.3 ?
C13B C12B H12B . . 119.3 ?
C8B C13B C12B . . 118.10(12) ?
C8B C13B C14B . . 122.27(12) ?
C12B C13B C14B . . 119.63(11) ?
C15B C14B C13B . . 123.55(13) ?
C15B C14B H14B . . 118.2 ?
C13B C14B H14B . . 118.2 ?
C14B C15B C16B . . 123.70(14) ?
C14B C15B H15B . . 118.1 ?
C16B C15B H15B . . 118.1 ?
N1B C16B C17B . . 118.35(14) ?
N1B C16B C15B . . 118.13(14) ?
C17B C16B C15B . . 123.52(13) ?
C18B C17B C16B . . 121.37(15) ?
C18B C17B H17B . . 119.3 ?
C16B C17B H17B . . 119.3 ?
C17B C18B C19B . . 118.62(18) ?
C17B C18B H18B . . 120.7 ?
C19B C18B H18B . . 120.7 ?
C20B C19B C18B . . 119.79(16) ?
C20B C19B H19B . . 120.1 ?
C18B C19B H19B . . 120.1 ?
C19B C20B N1B . . 121.37(16) ?
C19B C20B H20B . . 119.3 ?
N1B C20B H20B . . 119.3 ?
N1B C21B H21D . . 109.5 ?
N1B C21B H21E . . 109.5 ?
H21D C21B H21E . . 109.5 ?
N1B C21B H21F . . 109.5 ?
H21D C21B H21F . . 109.5 ?
H21E C21B H21F . . 109.5 ?
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
Cl1A C10A . 1.7406(14) ?
S1A O3A . 1.4512(11) ?
S1A O2A . 1.4515(11) ?
S1A O4A . 1.4531(11) ?
S1A C3A . 1.7720(13) ?
O1A C6A . 1.3614(16) ?
O1A C7A . 1.434(2) ?
N1A C20A . 1.356(2) ?
N1A C16A . 1.3744(18) ?
N1A C21A . 1.484(2) ?
C1A C2A . 1.3821(19) ?
C1A C6A . 1.4011(19) ?
C1A H1AA . 0.9300 ?
C2A C3A . 1.3998(16) ?
C2A H2AA . 0.9300 ?
C3A C4A . 1.3908(17) ?
C4A C5A . 1.3918(19) ?
C4A H4AA . 0.9300 ?
C5A C6A . 1.3941(19) ?
C5A H5AA . 0.9300 ?
C7A H7AA . 0.9600 ?
C7A H7AB . 0.9600 ?
C7A H7AC . 0.9600 ?
C8A C9A . 1.3853(19) ?
C8A C13A . 1.4096(18) ?
C8A H8AA . 0.9300 ?
C9A C10A . 1.3899(18) ?
C9A H9AA . 0.9300 ?
C10A C11A . 1.3932(18) ?
C11A C12A . 1.383(2) ?
C11A H11A . 0.9300 ?
C12A C13A . 1.4052(18) ?
C12A H12A . 0.9300 ?
C13A C14A . 1.4642(19) ?
C14A C15A . 1.3429(19) ?
C14A H14A . 0.9300 ?
C15A C16A . 1.4556(19) ?
C15A H15A . 0.9300 ?
C16A C17A . 1.393(2) ?
C17A C18A . 1.385(2) ?
C17A H17A . 0.9300 ?
C18A C19A . 1.389(3) ?
C18A H18A . 0.9300 ?
C19A C20A . 1.368(3) ?
C19A H19A . 0.9300 ?
C20A H20A . 0.9300 ?
C21A H21A . 0.9600 ?
C21A H21B . 0.9600 ?
C21A H21C . 0.9600 ?
Cl1B C10B . 1.7378(14) ?
S1B O4B . 1.4526(11) ?
S1B O2B . 1.4542(11) ?
S1B O3B . 1.4558(11) ?
S1B C3B . 1.7742(13) ?
O1B C6B . 1.3680(15) ?
O1B C7B . 1.4334(19) ?
N1B C20B . 1.367(2) ?
N1B C16B . 1.3758(18) ?
N1B C21B . 1.479(2) ?
C1B C2B . 1.3851(18) ?
C1B C6B . 1.3985(18) ?
C1B H1BA . 0.9300 ?
C2B C3B . 1.3980(17) ?
C2B H2BA . 0.9300 ?
C3B C4B . 1.3882(17) ?
C4B C5B . 1.3970(18) ?
C4B H4BA . 0.9300 ?
C5B C6B . 1.3919(18) ?
C5B H5BA . 0.9300 ?
C7B H7BA . 0.9600 ?
C7B H7BB . 0.9600 ?
C7B H7BC . 0.9600 ?
C8B C9B . 1.384(2) ?
C8B C13B . 1.4053(18) ?
C8B H8BA . 0.9300 ?
C9B C10B . 1.3867(19) ?
C9B H9BA . 0.9300 ?
C10B C11B . 1.3940(18) ?
C11B C12B . 1.3878(19) ?
C11B H11B . 0.9300 ?
C12B C13B . 1.4061(18) ?
C12B H12B . 0.9300 ?
C13B C14B . 1.4635(19) ?
C14B C15B . 1.3445(19) ?
C14B H14B . 0.9300 ?
C15B C16B . 1.457(2) ?
C15B H15B . 0.9300 ?
C16B C17B . 1.393(2) ?
C17B C18B . 1.385(2) ?
C17B H17B . 0.9300 ?
C18B C19B . 1.389(3) ?
C18B H18B . 0.9300 ?
C19B C20B . 1.365(3) ?
C19B H19B . 0.9300 ?
C20B H20B . 0.9300 ?
C21B H21D . 0.9600 ?
C21B H21E . 0.9600 ?
C21B H21F . 0.9600 ?
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
C1A H1AA O3B 1_455 0.93 2.53 3.3040(17) 141 y
C7A H7AB O3A 2_645 0.96 2.56 3.506(2) 171 y
C1B H1BA O3A 1_555 0.93 2.31 3.2373(17) 172 y
C12B H12B O2B 1_455 0.93 2.47 3.2817(17) 146 y
C7B H7BA O4A 2_645 0.96 2.57 3.518(2) 171 y
C14B H14B O3B 1_455 0.93 2.59 3.5204(19) 176 y
C15A H15A O2A 4_576 0.93 2.47 3.2626(19) 143 y
C17B H17B O3B 1_455 0.93 2.58 3.474(2) 161 y
C20A H20A O4A 3_666 0.93 2.50 3.159(2) 128 y
C20B H20B O4B 4_475 0.93 2.38 3.185(2) 144 y
C21A H21C O2A 4_576 0.96 2.29 3.162(2) 150 y
C21B H21D O2B 3_675 0.96 2.42 3.317(2) 156 y
C9A H9AA Cg3 4_576 0.93 2.70 3.4423(13) 137 y
C11A H11A Cg3 1_555 0.93 2.59 3.3482(13) 139 y
C11B H11B Cg4 2_655 0.93 2.77 3.5457(14) 142 y
C9B H9BA Cg4 3_675 0.93 2.62 3.3442(13) 135 y
C21A H21B Cg2 4_576 0.96 2.82 3.6853(18) 151 y
C21B H21F Cg1 4_574 0.96 2.82 3.7100(19) 155 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
C6A C1A C2A C3A . . . . -1.3(2) ?
C1A C2A C3A C4A . . . . 0.37(19) ?
C1A C2A C3A S1A . . . . -179.50(10) ?
O3A S1A C3A C4A . . . . 3.32(13) ?
O2A S1A C3A C4A . . . . 123.36(12) ?
O4A S1A C3A C4A . . . . -116.73(11) ?
O3A S1A C3A C2A . . . . -176.81(11) ?
O2A S1A C3A C2A . . . . -56.77(12) ?
O4A S1A C3A C2A . . . . 63.14(12) ?
C2A C3A C4A C5A . . . . 0.64(19) ?
S1A C3A C4A C5A . . . . -179.48(10) ?
C3A C4A C5A C6A . . . . -0.67(19) ?
C7A O1A C6A C5A . . . . -16.38(19) ?
C7A O1A C6A C1A . . . . 163.36(13) ?
C4A C5A C6A O1A . . . . 179.42(12) ?
C4A C5A C6A C1A . . . . -0.31(19) ?
C2A C1A C6A O1A . . . . -178.45(12) ?
C2A C1A C6A C5A . . . . 1.3(2) ?
C13A C8A C9A C10A . . . . -0.7(2) ?
C8A C9A C10A C11A . . . . -0.2(2) ?
C8A C9A C10A Cl1A . . . . 178.29(10) ?
C9A C10A C11A C12A . . . . 0.9(2) ?
Cl1A C10A C11A C12A . . . . -177.56(10) ?
C10A C11A C12A C13A . . . . -0.8(2) ?
C11A C12A C13A C8A . . . . -0.09(19) ?
C11A C12A C13A C14A . . . . 179.97(12) ?
C9A C8A C13A C12A . . . . 0.84(19) ?
C9A C8A C13A C14A . . . . -179.22(13) ?
C12A C13A C14A C15A . . . . 172.88(13) ?
C8A C13A C14A C15A . . . . -7.1(2) ?
C13A C14A C15A C16A . . . . 178.86(12) ?
C20A N1A C16A C17A . . . . 1.17(19) ?
C21A N1A C16A C17A . . . . -178.46(12) ?
C20A N1A C16A C15A . . . . -179.14(12) ?
C21A N1A C16A C15A . . . . 1.22(18) ?
C14A C15A C16A N1A . . . . -177.99(13) ?
C14A C15A C16A C17A . . . . 1.7(2) ?
N1A C16A C17A C18A . . . . 0.2(2) ?
C15A C16A C17A C18A . . . . -179.44(13) ?
C16A C17A C18A C19A . . . . -1.2(2) ?
C17A C18A C19A C20A . . . . 0.7(2) ?
C16A N1A C20A C19A . . . . -1.6(2) ?
C21A N1A C20A C19A . . . . 178.03(13) ?
C18A C19A C20A N1A . . . . 0.6(2) ?
C6B C1B C2B C3B . . . . -1.37(19) ?
C1B C2B C3B C4B . . . . 1.88(19) ?
C1B C2B C3B S1B . . . . -177.39(10) ?
O4B S1B C3B C4B . . . . -108.83(11) ?
O2B S1B C3B C4B . . . . 131.27(11) ?
O3B S1B C3B C4B . . . . 11.27(13) ?
O4B S1B C3B C2B . . . . 70.43(12) ?
O2B S1B C3B C2B . . . . -49.47(12) ?
O3B S1B C3B C2B . . . . -169.48(11) ?
C2B C3B C4B C5B . . . . -0.67(19) ?
S1B C3B C4B C5B . . . . 178.59(10) ?
C3B C4B C5B C6B . . . . -1.04(19) ?
C7B O1B C6B C5B . . . . -4.32(19) ?
C7B O1B C6B C1B . . . . 174.76(13) ?
C4B C5B C6B O1B . . . . -179.40(12) ?
C4B C5B C6B C1B . . . . 1.57(19) ?
C2B C1B C6B O1B . . . . -179.49(11) ?
C2B C1B C6B C5B . . . . -0.38(19) ?
C13B C8B C9B C10B . . . . -0.5(2) ?
C8B C9B C10B C11B . . . . 1.0(2) ?
C8B C9B C10B Cl1B . . . . -179.60(11) ?
C9B C10B C11B C12B . . . . -0.4(2) ?
Cl1B C10B C11B C12B . . . . -179.82(10) ?
C10B C11B C12B C13B . . . . -0.6(2) ?
C9B C8B C13B C12B . . . . -0.5(2) ?
C9B C8B C13B C14B . . . . 179.93(13) ?
C11B C12B C13B C8B . . . . 1.10(19) ?
C11B C12B C13B C14B . . . . -179.34(12) ?
C8B C13B C14B C15B . . . . -17.2(2) ?
C12B C13B C14B C15B . . . . 163.30(13) ?
C13B C14B C15B C16B . . . . 178.33(12) ?
C20B N1B C16B C17B . . . . 0.2(2) ?
C21B N1B C16B C17B . . . . -179.88(13) ?
C20B N1B C16B C15B . . . . -179.62(13) ?
C21B N1B C16B C15B . . . . 0.34(19) ?
C14B C15B C16B N1B . . . . -166.95(13) ?
C14B C15B C16B C17B . . . . 13.3(2) ?
N1B C16B C17B C18B . . . . 1.1(2) ?
C15B C16B C17B C18B . . . . -179.12(14) ?
C16B C17B C18B C19B . . . . -1.1(2) ?
C17B C18B C19B C20B . . . . -0.2(2) ?
C18B C19B C20B N1B . . . . 1.5(2) ?
C16B N1B C20B C19B . . . . -1.5(2) ?
C21B N1B C20B C19B . . . . 178.56(15) ?
