#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/09/2220915.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_2220915
loop_
_publ_author_name
'Chantrapromma, Suchada'
'Fun, Hoong-Kun'
_publ_section_title
;
 Bis{4-[(E)-2-(1H-indol-3-yl)ethenyl]-1-methylpyridinium}
 4-fluorobenzenesulfonate nitrate 0.25-hydrate
;
_journal_coeditor_code           SJ2569
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o258
_journal_page_last               o259
_journal_paper_doi               10.1107/S1600536809000026
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac
'2C16 H15 N2 + , C6 H4 F O3 S - , N O3 - , 0.25H2 O'
_chemical_formula_moiety
'2C16 H15 N2 + , C6 H4 F O3 S - , N O3 - , 0.25H2 O'
_chemical_formula_sum            'C38 H34.5 F N5 O6.25 S'
_chemical_formula_weight         712.27
_chemical_name_systematic
;
Bis{4-[(E)-2-(1H-indol-3-yl)ethenyl]-1-methylpyridinium}
4-fluorobenzenesulfonate nitrate 0.25-hydrate
;
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                97.5200(10)
_cell_angle_beta                 91.2360(10)
_cell_angle_gamma                99.8610(10)
_cell_formula_units_Z            2
_cell_length_a                   8.7750(6)
_cell_length_b                   13.63660(10)
_cell_length_c                   15.3190(11)
_cell_measurement_reflns_used    6287
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.34
_cell_volume                     1788.66(18)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_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      297(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_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_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17243
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.9823
_exptl_absorpt_correction_T_min  0.9187
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             745
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.249
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     520
_refine_ls_number_reflns         6287
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0626
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1048P)²+0.7458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1795
_refine_ls_wR_factor_ref         0.1985
_reflns_number_gt                4818
_reflns_number_total             6287
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2569.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C38 H34.50 F N5 O6.25 S'
_cod_database_code               2220915
_cod_database_fobs_code          2220915
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
F F1 0.8301(3) 0.53738(13) 0.13528(13) 0.1070(7) Uani d . 1 A .
S S1 0.74535(14) 0.96215(6) 0.30690(6) 0.0943(4) Uani d . 1 . .
O O1A 0.7947(14) 0.9676(5) 0.3874(4) 0.128(4) Uani d P 0.535(10) A 1
O O2A 0.5540(7) 0.9537(4) 0.3014(6) 0.122(3) Uani d P 0.535(10) A 1
O O3A 0.7858(15) 1.0287(7) 0.2507(7) 0.117(4) Uani d P 0.535(10) A 1
O O1B 0.6669(17) 0.9575(5) 0.3770(7) 0.148(7) Uani d P 0.465(10) A 2
O O2B 0.7404(16) 1.0297(9) 0.2476(7) 0.106(4) Uani d P 0.465(10) A 2
O O3B 0.9324(9) 1.0071(5) 0.3454(6) 0.123(3) Uani d P 0.465(10) A 2
O O4 0.7248(4) 0.3823(2) 0.8149(2) 0.1299(11) Uani d . 1 . .
O O5 0.7224(8) 0.3889(4) 0.9475(3) 0.241(3) Uani d . 1 . .
O O6 0.6872(4) 0.2501(2) 0.8724(3) 0.1355(12) Uani d . 1 . .
N N1 1.1622(3) 0.86382(16) 0.41062(15) 0.0630(6) Uani d . 1 . .
N N2 0.7682(3) 0.22728(16) 0.34872(16) 0.0698(6) Uani d . 1 . .
H H1N2 0.7686 0.1677 0.3223 0.084 Uiso calc R 1 . .
N N3 0.4743(3) 1.1617(2) 1.09022(17) 0.0769(7) Uani d . 1 . .
N N4 -0.1419(3) 0.6053(2) 0.88513(19) 0.0872(8) Uani d . 1 B .
H H1N4 -0.1724 0.5431 0.8904 0.105 Uiso calc R 1 . .
N N5 0.7084(3) 0.3399(2) 0.8801(2) 0.0836(7) Uani d . 1 . .
C C1 0.7643(3) 0.84191(19) 0.25284(17) 0.0626(7) Uani d . 1 A .
C C2 0.9019(4) 0.8268(2) 0.21795(19) 0.0722(8) Uani d . 1 . .
H H2A 0.9835 0.8806 0.2195 0.087 Uiso calc R 1 A .
C C3 0.9200(4) 0.7333(3) 0.1809(2) 0.0806(9) Uani d . 1 A .
H H3A 1.0139 0.7239 0.1571 0.097 Uiso calc R 1 . .
C C4 0.8020(4) 0.6533(2) 0.1782(2) 0.0771(8) Uani d . 1 . .
C C5 0.6630(4) 0.6681(2) 0.2113(2) 0.0877(10) Uani d . 1 A .
H H5A 0.5814 0.6142 0.2089 0.105 Uiso calc R 1 . .
C C6 0.6433(4) 0.7629(2) 0.2484(2) 0.0800(9) Uani d . 1 . .
H H6A 0.5483 0.7731 0.2703 0.096 Uiso calc R 1 A .
C C7 1.1090(3) 0.6898(2) 0.36194(18) 0.0651(7) Uani d . 1 . .
H H7A 1.1316 0.6350 0.3248 0.078 Uiso calc R 1 . .
C C8 1.1910(3) 0.7838(2) 0.35711(19) 0.0686(7) Uani d . 1 . .
H H8A 1.2674 0.7922 0.3163 0.082 Uiso calc R 1 . .
C C9 1.0525(3) 0.8512(2) 0.46932(19) 0.0674(7) Uani d . 1 . .
H H9A 1.0334 0.9067 0.5068 0.081 Uiso calc R 1 . .
C C10 0.9685(3) 0.75962(19) 0.47560(19) 0.0646(7) Uani d . 1 . .
H H10A 0.8930 0.7536 0.5172 0.078 Uiso calc R 1 . .
C C11 0.9924(3) 0.67502(18) 0.42152(16) 0.0547(6) Uani d . 1 . .
C C12 0.9001(3) 0.57771(19) 0.42901(17) 0.0595(6) Uani d . 1 . .
H H12A 0.8248 0.5754 0.4708 0.071 Uiso calc R 1 . .
C C13 0.9144(3) 0.49223(19) 0.38127(18) 0.0618(6) Uani d . 1 . .
H H13A 0.9893 0.4968 0.3393 0.074 Uiso calc R 1 . .
C C14 0.8305(3) 0.39367(18) 0.38538(17) 0.0577(6) Uani d . 1 . .
C C15 0.8606(4) 0.3107(2) 0.33221(19) 0.0696(7) Uani d . 1 . .
H H15A 0.9356 0.3124 0.2902 0.084 Uiso calc R 1 . .
C C16 0.6722(3) 0.25210(18) 0.41484(18) 0.0584(6) Uani d . 1 . .
C C17 0.5603(3) 0.1904(2) 0.4537(2) 0.0702(8) Uani d . 1 . .
H H17A 0.5400 0.1213 0.4363 0.084 Uiso calc R 1 . .
C C18 0.4800(3) 0.2348(2) 0.5189(2) 0.0785(9) Uani d . 1 . .
H H18A 0.4033 0.1952 0.5461 0.094 Uiso calc R 1 . .
C C19 0.5115(3) 0.3387(2) 0.5452(2) 0.0762(8) Uani d . 1 . .
H H19A 0.4550 0.3669 0.5894 0.091 Uiso calc R 1 . .
C C20 0.6248(3) 0.3999(2) 0.50683(18) 0.0626(7) Uani d . 1 . .
H H20A 0.6455 0.4688 0.5252 0.075 Uiso calc R 1 . .
C C21 0.7077(3) 0.35702(17) 0.44012(16) 0.0529(6) Uani d . 1 . .
C C22 1.2493(5) 0.9649(2) 0.4041(3) 0.0987(11) Uani d . 1 . .
H H22A 1.2723 1.0015 0.4622 0.148 Uiso calc R 1 . .
H H22B 1.1881 1.0000 0.3705 0.148 Uiso calc R 1 . .
H H22C 1.3441 0.9591 0.3754 0.148 Uiso calc R 1 . .
C C23 0.3467(6) 0.9948(3) 1.0839(4) 0.1117(15) Uani d . 1 B .
H H23A 0.3336 0.9347 1.1075 0.134 Uiso calc R 1 . .
C C24 0.4531(5) 1.0744(3) 1.1227(2) 0.0925(10) Uani d . 1 . .
H H24A 0.5114 1.0677 1.1723 0.111 Uiso calc R 1 . .
C C25 0.3890(4) 1.1693(3) 1.0182(2) 0.0797(8) Uani d . 1 . .
H H25A 0.4030 1.2297 0.9950 0.096 Uiso calc R 1 . .
C C26 0.2841(4) 1.0915(3) 0.9792(2) 0.0863(10) Uani d . 1 B .
H H26A 0.2278 1.0998 0.9293 0.104 Uiso calc R 1 . .
C C27 0.2572(4) 1.0021(3) 1.0093(3) 0.0964(11) Uani d . 1 . .
C C28A 0.1315(7) 0.9283(6) 0.9502(4) 0.077(2) Uani d P 0.685(12) B 1
H H28A 0.0848 0.9499 0.9028 0.093 Uiso calc PR 0.685(12) B 1
C C29A 0.0901(6) 0.8359(5) 0.9661(4) 0.075(2) Uani d P 0.685(12) B 1
H H29A 0.1347 0.8176 1.0158 0.090 Uiso calc PR 0.685(12) B 1
C C28B 0.1802(10) 0.8954(7) 1.0036(6) 0.052(3) Uani d P 0.315(12) B 2
H H28B 0.1980 0.8505 1.0419 0.062 Uiso calc PR 0.315(12) B 2
C C29B 0.0751(16) 0.8741(10) 0.9296(8) 0.057(3) Uani d P 0.315(12) B 2
H H29B 0.0611 0.9218 0.8933 0.068 Uiso calc PR 0.315(12) B 2
C C30 -0.0168(4) 0.7624(3) 0.9137(2) 0.0847(10) Uani d . 1 . .
C C31 -0.0391(4) 0.6689(3) 0.9388(2) 0.0946(10) Uani d . 1 B .
H H31A 0.0111 0.6520 0.9873 0.114 Uiso calc R 1 . .
C C32 -0.1923(3) 0.6535(2) 0.81984(19) 0.0657(7) Uani d . 1 . .
C C33 -0.2938(3) 0.6159(2) 0.7491(2) 0.0756(8) Uani d . 1 B .
H H33A -0.3421 0.5489 0.7402 0.091 Uiso calc R 1 . .
C C34 -0.3209(4) 0.6814(3) 0.6919(2) 0.0849(9) Uani d . 1 . .
H H34A -0.3887 0.6584 0.6432 0.102 Uiso calc R 1 B .
C C35 -0.2491(4) 0.7807(3) 0.7056(2) 0.0885(10) Uani d . 1 B .
H H35A -0.2702 0.8234 0.6660 0.106 Uiso calc R 1 . .
C C36 -0.1480(4) 0.8182(2) 0.7758(2) 0.0803(9) Uani d . 1 . .
H H36A -0.1004 0.8853 0.7840 0.096 Uiso calc R 1 B .
C C37 -0.1175(3) 0.7536(2) 0.83492(19) 0.0661(7) Uani d . 1 B .
C C38 0.5860(4) 1.2495(3) 1.1315(3) 0.1201(15) Uani d . 1 . .
H H38A 0.6153 1.2939 1.0887 0.180 Uiso calc R 1 . .
H H38B 0.6761 1.2276 1.1532 0.180 Uiso calc R 1 . .
H H38C 0.5393 1.2842 1.1795 0.180 Uiso calc R 1 . .
O O1W 0.4653(13) 0.4288(9) 0.0301(9) 0.128(4) Uani d P 0.25 . .
H H1W1 0.5529 0.4619 0.0500 0.192 Uiso d PR 0.25 . .
H H2W1 0.4351 0.4572 -0.0116 0.192 Uiso d PR 0.25 . .
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'
F F 0.0171 0.0103 '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
O1A S1 O1B . . 51.1(5) ?
O1A S1 O3A . . 127.5(7) ?
O1B S1 O3A . . 137.3(6) ?
O1A S1 O2B . . 135.5(6) ?
O1B S1 O2B . . 125.9(7) ?
O1A S1 O2A . . 110.4(6) ?
O1B S1 O2A . . 59.4(6) ?
O3A S1 O2A . . 100.2(6) ?
O2B S1 O2A . . 83.2(6) ?
O1A S1 O3B . . 55.1(5) ?
O1B S1 O3B . . 104.6(7) ?
O3A S1 O3B . . 80.9(6) ?
O2B S1 O3B . . 96.4(6) ?
O2A S1 O3B . . 157.3(3) ?
O1A S1 C1 . . 107.2(3) ?
O1B S1 C1 . . 112.7(3) ?
O3A S1 C1 . . 107.6(5) ?
O2B S1 C1 . . 111.5(5) ?
O2A S1 C1 . . 100.7(2) ?
O3B S1 C1 . . 100.5(2) ?
C9 N1 C8 . . 119.3(2) ?
C9 N1 C22 . . 120.3(3) ?
C8 N1 C22 . . 120.4(3) ?
C15 N2 C16 . . 109.0(2) ?
C15 N2 H1N2 . . 125.5 ?
C16 N2 H1N2 . . 125.5 ?
C24 N3 C25 . . 118.5(3) ?
C24 N3 C38 . . 122.0(4) ?
C25 N3 C38 . . 119.5(3) ?
C31 N4 C32 . . 109.9(3) ?
C31 N4 H1N4 . . 125.0 ?
C32 N4 H1N4 . . 125.0 ?
O5 N5 O6 . . 122.5(5) ?
O5 N5 O4 . . 117.6(5) ?
O6 N5 O4 . . 119.8(4) ?
C2 C1 C6 . . 119.6(3) ?
C2 C1 S1 . . 120.0(2) ?
C6 C1 S1 . . 120.3(2) ?
C3 C2 C1 . . 120.3(3) ?
C3 C2 H2A . . 119.9 ?
C1 C2 H2A . . 119.9 ?
C2 C3 C4 . . 120.8(3) ?
C2 C3 H3A . . 119.6 ?
C4 C3 H3A . . 119.6 ?
C3 C4 C5 . . 119.3(3) ?
C3 C4 F1 . . 119.7(3) ?
C5 C4 F1 . . 120.9(3) ?
C4 C5 C6 . . 120.2(3) ?
C4 C5 H5A . . 119.9 ?
C6 C5 H5A . . 119.9 ?
C1 C6 C5 . . 119.7(3) ?
C1 C6 H6A . . 120.1 ?
C5 C6 H6A . . 120.1 ?
C8 C7 C11 . . 121.0(3) ?
C8 C7 H7A . . 119.5 ?
C11 C7 H7A . . 119.5 ?
N1 C8 C7 . . 120.7(3) ?
N1 C8 H8A . . 119.7 ?
C7 C8 H8A . . 119.7 ?
N1 C9 C10 . . 121.7(3) ?
N1 C9 H9A . . 119.2 ?
C10 C9 H9A . . 119.2 ?
C9 C10 C11 . . 121.3(3) ?
C9 C10 H10A . . 119.3 ?
C11 C10 H10A . . 119.3 ?
C10 C11 C7 . . 115.9(2) ?
C10 C11 C12 . . 120.4(2) ?
C7 C11 C12 . . 123.7(2) ?
C13 C12 C11 . . 125.3(3) ?
C13 C12 H12A . . 117.4 ?
C11 C12 H12A . . 117.4 ?
C12 C13 C14 . . 128.8(3) ?
C12 C13 H13A . . 115.6 ?
C14 C13 H13A . . 115.6 ?
C15 C14 C13 . . 122.2(3) ?
C15 C14 C21 . . 105.9(2) ?
C13 C14 C21 . . 131.9(2) ?
N2 C15 C14 . . 111.1(3) ?
N2 C15 H15A . . 124.4 ?
C14 C15 H15A . . 124.4 ?
N2 C16 C17 . . 129.2(3) ?
N2 C16 C21 . . 107.9(2) ?
C17 C16 C21 . . 123.0(3) ?
C18 C17 C16 . . 117.4(3) ?
C18 C17 H17A . . 121.3 ?
C16 C17 H17A . . 121.3 ?
C17 C18 C19 . . 121.1(3) ?
C17 C18 H18A . . 119.4 ?
C19 C18 H18A . . 119.4 ?
C20 C19 C18 . . 121.2(3) ?
C20 C19 H19A . . 119.4 ?
C18 C19 H19A . . 119.4 ?
C19 C20 C21 . . 119.0(3) ?
C19 C20 H20A . . 120.5 ?
C21 C20 H20A . . 120.5 ?
C20 C21 C16 . . 118.3(2) ?
C20 C21 C14 . . 135.6(2) ?
C16 C21 C14 . . 106.1(2) ?
N1 C22 H22A . . 109.5 ?
N1 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
N1 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C24 C23 C27 . . 121.2(4) ?
C24 C23 H23A . . 119.4 ?
C27 C23 H23A . . 119.4 ?
N3 C24 C23 . . 120.7(4) ?
N3 C24 H24A . . 119.6 ?
C23 C24 H24A . . 119.6 ?
N3 C25 C26 . . 121.5(3) ?
N3 C25 H25A . . 119.3 ?
C26 C25 H25A . . 119.3 ?
C27 C26 C25 . . 122.6(4) ?
C27 C26 H26A . . 118.7 ?
C25 C26 H26A . . 118.7 ?
C26 C27 C23 . . 115.6(4) ?
C26 C27 C28B . . 152.5(6) ?
C23 C27 C28B . . 91.9(5) ?
C26 C27 C28A . . 110.3(5) ?
C23 C27 C28A . . 134.2(5) ?
C29A C28A C27 . . 120.6(6) ?
C29A C28A H28A . . 119.7 ?
C27 C28A H28A . . 119.7 ?
C28A C29A C30 . . 124.6(7) ?
C28A C29A H29A . . 117.7 ?
C30 C29A H29A . . 117.7 ?
C29B C28B C27 . . 107.8(9) ?
C29B C28B H28B . . 126.1 ?
C27 C28B H28B . . 126.1 ?
C28B C29B C30 . . 114.3(10) ?
C28B C29B H29B . . 122.8 ?
C30 C29B H29B . . 122.8 ?
C31 C30 C29A . . 115.9(5) ?
C31 C30 C37 . . 105.4(3) ?
C29A C30 C37 . . 138.7(5) ?
C31 C30 C29B . . 147.6(6) ?
C37 C30 C29B . . 106.9(6) ?
N4 C31 C30 . . 111.1(3) ?
N4 C31 H31A . . 124.5 ?
C30 C31 H31A . . 124.5 ?
N4 C32 C33 . . 129.5(3) ?
N4 C32 C37 . . 107.6(3) ?
C33 C32 C37 . . 122.8(3) ?
C32 C33 C34 . . 117.2(3) ?
C32 C33 H33A . . 121.4 ?
C34 C33 H33A . . 121.4 ?
C33 C34 C35 . . 121.0(3) ?
C33 C34 H34A . . 119.5 ?
C35 C34 H34A . . 119.5 ?
C36 C35 C34 . . 121.9(3) ?
C36 C35 H35A . . 119.1 ?
C34 C35 H35A . . 119.1 ?
C35 C36 C37 . . 118.6(3) ?
C35 C36 H36A . . 120.7 ?
C37 C36 H36A . . 120.7 ?
C36 C37 C32 . . 118.5(3) ?
C36 C37 C30 . . 135.4(3) ?
C32 C37 C30 . . 106.0(3) ?
N3 C38 H38A . . 109.5 ?
N3 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
N3 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
H1W1 O1W H2W1 . . 107.7 ?
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
F1 C4 . 1.692(3) ?
S1 O1A . 1.287(6) ?
S1 O1B . 1.291(6) ?
S1 O3A . 1.340(8) ?
S1 O2B . 1.381(11) ?
S1 O2A . 1.662(6) ?
S1 O3B . 1.714(7) ?
S1 C1 . 1.774(3) ?
O4 N5 . 1.217(4) ?
O5 N5 . 1.145(4) ?
O6 N5 . 1.197(4) ?
N1 C9 . 1.336(4) ?
N1 C8 . 1.340(4) ?
N1 C22 . 1.474(3) ?
N2 C15 . 1.336(4) ?
N2 C16 . 1.376(4) ?
N2 H1N2 . 0.8600 ?
N3 C24 . 1.336(5) ?
N3 C25 . 1.344(4) ?
N3 C38 . 1.471(4) ?
N4 C31 . 1.324(4) ?
N4 C32 . 1.371(4) ?
N4 H1N4 . 0.8600 ?
C1 C2 . 1.368(4) ?
C1 C6 . 1.370(4) ?
C2 C3 . 1.363(4) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.365(5) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.367(5) ?
C5 C6 . 1.383(4) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
C7 C8 . 1.370(4) ?
C7 C11 . 1.392(4) ?
C7 H7A . 0.9300 ?
C8 H8A . 0.9300 ?
C9 C10 . 1.353(4) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.379(4) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.451(3) ?
C12 C13 . 1.319(4) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.428(4) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.373(4) ?
C14 C21 . 1.441(4) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.378(4) ?
C16 C21 . 1.411(3) ?
C17 C18 . 1.371(4) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.398(4) ?
C18 H18A . 0.9300 ?
C19 C20 . 1.378(4) ?
C19 H19A . 0.9300 ?
C20 C21 . 1.392(4) ?
C20 H20A . 0.9300 ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
C23 C24 . 1.365(6) ?
C23 C27 . 1.396(6) ?
C23 H23A . 0.9300 ?
C24 H24A . 0.9300 ?
C25 C26 . 1.345(5) ?
C25 H25A . 0.9300 ?
C26 C27 . 1.345(5) ?
C26 H26A . 0.9300 ?
C27 C28B . 1.487(10) ?
C27 C28A . 1.546(8) ?
C28A C29A . 1.306(12) ?
C28A H28A . 0.9300 ?
C29A C30 . 1.402(7) ?
C29A H29A . 0.9300 ?
C28B C29B . 1.41(2) ?
C28B H28B . 0.9300 ?
C29B C30 . 1.583(15) ?
C29B H29B . 0.9300 ?
C30 C31 . 1.364(5) ?
C30 C37 . 1.459(4) ?
C31 H31A . 0.9300 ?
C32 C33 . 1.374(4) ?
C32 C37 . 1.397(4) ?
C33 C34 . 1.376(4) ?
C33 H33A . 0.9300 ?
C34 C35 . 1.379(5) ?
C34 H34A . 0.9300 ?
C35 C36 . 1.364(5) ?
C35 H35A . 0.9300 ?
C36 C37 . 1.396(4) ?
C36 H36A . 0.9300 ?
C38 H38A . 0.9600 ?
C38 H38B . 0.9600 ?
C38 H38C . 0.9600 ?
O1W H1W1 . 0.8500 ?
O1W H2W1 . 0.8500 ?
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
N2 H1N2 O3A 1_545 0.86 2.09 2.950(10) 175 y
N4 H1N4 O4 1_455 0.86 2.36 3.106(4) 145 y
N4 H1N4 O5 1_455 0.86 2.43 3.259(6) 163 y
O1W H1W1 O5 1_554 0.85 2.42 2.711(14) 101 y
C6 H6A O2A 1_555 0.93 2.44 2.866(7) 108 y
C7 H7A O4 2_766 0.93 2.51 3.224(4) 134 y
C9 H9A O1A 2_776 0.93 2.47 3.169(8) 132 y
C22 H22A O1A 2_776 0.96 2.39 3.256(8) 149 y
C22 H22C O2A 1_655 0.96 2.19 3.147(8) 175 y
C23 H23A O6 2_667 0.93 2.55 3.456(5) 164 y
C15 H15A Cg1 2_666 0.93 2.99 3.896(3) 164 y
C15 H15A Cg2 2_666 0.93 2.72 3.563(4) 151 y
C34 H34A Cg3 2_566 0.93 2.78 3.595(4) 147 y
C38 H38C Cg2 2_577 0.96 2.95 3.695(4) 135 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
O1A S1 C1 C2 . . . . -85.3(6) ?
O1B S1 C1 C2 . . . . -139.6(8) ?
O3A S1 C1 C2 . . . . 54.9(6) ?
O2B S1 C1 C2 . . . . 72.4(7) ?
O2A S1 C1 C2 . . . . 159.3(4) ?
O3B S1 C1 C2 . . . . -28.8(4) ?
O1A S1 C1 C6 . . . . 92.5(6) ?
O1B S1 C1 C6 . . . . 38.2(8) ?
O3A S1 C1 C6 . . . . -127.4(7) ?
O2B S1 C1 C6 . . . . -109.8(7) ?
O2A S1 C1 C6 . . . . -23.0(4) ?
O3B S1 C1 C6 . . . . 149.0(4) ?
C6 C1 C2 C3 . . . . -1.6(5) ?
S1 C1 C2 C3 . . . . 176.2(2) ?
C1 C2 C3 C4 . . . . -0.3(5) ?
C2 C3 C4 C5 . . . . 1.6(5) ?
C2 C3 C4 F1 . . . . -177.7(2) ?
C3 C4 C5 C6 . . . . -1.1(5) ?
F1 C4 C5 C6 . . . . 178.2(3) ?
C2 C1 C6 C5 . . . . 2.1(5) ?
S1 C1 C6 C5 . . . . -175.7(3) ?
C4 C5 C6 C1 . . . . -0.8(5) ?
C9 N1 C8 C7 . . . . 0.2(4) ?
C22 N1 C8 C7 . . . . -179.1(3) ?
C11 C7 C8 N1 . . . . 0.9(4) ?
C8 N1 C9 C10 . . . . -0.7(4) ?
C22 N1 C9 C10 . . . . 178.6(3) ?
N1 C9 C10 C11 . . . . 0.0(4) ?
C9 C10 C11 C7 . . . . 1.0(4) ?
C9 C10 C11 C12 . . . . -179.6(2) ?
C8 C7 C11 C10 . . . . -1.4(4) ?
C8 C7 C11 C12 . . . . 179.1(2) ?
C10 C11 C12 C13 . . . . -179.4(3) ?
C7 C11 C12 C13 . . . . 0.0(4) ?
C11 C12 C13 C14 . . . . 178.9(2) ?
C12 C13 C14 C15 . . . . -178.6(3) ?
C12 C13 C14 C21 . . . . 0.4(5) ?
C16 N2 C15 C14 . . . . -0.3(3) ?
C13 C14 C15 N2 . . . . 179.5(2) ?
C21 C14 C15 N2 . . . . 0.3(3) ?
C15 N2 C16 C17 . . . . -179.1(3) ?
C15 N2 C16 C21 . . . . 0.2(3) ?
N2 C16 C17 C18 . . . . -180.0(3) ?
C21 C16 C17 C18 . . . . 0.8(4) ?
C16 C17 C18 C19 . . . . -0.4(4) ?
C17 C18 C19 C20 . . . . -0.3(5) ?
C18 C19 C20 C21 . . . . 0.6(4) ?
C19 C20 C21 C16 . . . . -0.2(4) ?
C19 C20 C21 C14 . . . . 180.0(3) ?
N2 C16 C21 C20 . . . . -179.9(2) ?
C17 C16 C21 C20 . . . . -0.5(4) ?
N2 C16 C21 C14 . . . . 0.0(3) ?
C17 C16 C21 C14 . . . . 179.4(2) ?
C15 C14 C21 C20 . . . . 179.7(3) ?
C13 C14 C21 C20 . . . . 0.6(5) ?
C15 C14 C21 C16 . . . . -0.2(3) ?
C13 C14 C21 C16 . . . . -179.2(3) ?
C25 N3 C24 C23 . . . . -0.3(5) ?
C38 N3 C24 C23 . . . . 178.8(3) ?
C27 C23 C24 N3 . . . . 0.0(5) ?
C24 N3 C25 C26 . . . . 0.1(4) ?
C38 N3 C25 C26 . . . . -179.0(3) ?
N3 C25 C26 C27 . . . . 0.3(5) ?
C25 C26 C27 C23 . . . . -0.5(5) ?
C25 C26 C27 C28B . . . . -175.9(8) ?
C25 C26 C27 C28A . . . . -179.6(3) ?
C24 C23 C27 C26 . . . . 0.4(5) ?
C24 C23 C27 C28B . . . . 178.2(4) ?
C24 C23 C27 C28A . . . . 179.2(4) ?
C26 C27 C28A C29A . . . . 178.2(4) ?
C23 C27 C28A C29A . . . . -0.7(8) ?
C28B C27 C28A C29A . . . . 0.7(5) ?
C27 C28A C29A C30 . . . . -176.6(4) ?
C26 C27 C28B C29B . . . . -3.5(13) ?
C23 C27 C28B C29B . . . . -179.3(6) ?
C28A C27 C28B C29B . . . . 1.7(6) ?
C27 C28B C29B C30 . . . . 179.7(6) ?
C28A C29A C30 C31 . . . . 176.9(5) ?
C28A C29A C30 C37 . . . . -2.4(8) ?
C28A C29A C30 C29B . . . . 0.9(8) ?
C28B C29B C30 C31 . . . . -3.8(13) ?
C28B C29B C30 C29A . . . . 2.9(5) ?
C28B C29B C30 C37 . . . . -179.3(6) ?
C32 N4 C31 C30 . . . . 0.9(4) ?
C29A C30 C31 N4 . . . . -180.0(3) ?
C37 C30 C31 N4 . . . . -0.5(4) ?
C29B C30 C31 N4 . . . . -176.0(7) ?
C31 N4 C32 C33 . . . . 177.5(3) ?
C31 N4 C32 C37 . . . . -0.8(4) ?
N4 C32 C33 C34 . . . . -178.3(3) ?
C37 C32 C33 C34 . . . . -0.2(4) ?
C32 C33 C34 C35 . . . . -0.2(5) ?
C33 C34 C35 C36 . . . . 0.4(5) ?
C34 C35 C36 C37 . . . . -0.1(5) ?
C35 C36 C37 C32 . . . . -0.2(4) ?
C35 C36 C37 C30 . . . . 177.6(3) ?
N4 C32 C37 C36 . . . . 178.9(3) ?
C33 C32 C37 C36 . . . . 0.4(4) ?
N4 C32 C37 C30 . . . . 0.5(3) ?
C33 C32 C37 C30 . . . . -178.0(3) ?
C31 C30 C37 C36 . . . . -178.0(3) ?
C29A C30 C37 C36 . . . . 1.3(7) ?
C29B C30 C37 C36 . . . . -0.5(6) ?
C31 C30 C37 C32 . . . . 0.0(3) ?
C29A C30 C37 C32 . . . . 179.3(4) ?
C29B C30 C37 C32 . . . . 177.5(4) ?
