#------------------------------------------------------------------------------
#$Date: 2016-11-28 13:28:16 +0200 (Mon, 28 Nov 2016) $
#$Revision: 188723 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/06/2220695.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_2220695
loop_
_publ_author_name
'Rodrigues, Tiago'
'Moreira, Rui'
'Dacunha-Marinho, Bruno'
'Lopes, Francisca'
_publ_section_title
;Bis{(E)-3-[(diethylmethylammonio)methyl]-N-[3-(N,N-dimethylsulfamoyl)-1-methylpyridin-4-ylidene]-4-methoxyanilinium}
 tetraiodide pentahydrate
;
_journal_coeditor_code           BG2227
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o283
_journal_page_last               o284
_journal_paper_doi               10.1107/S1600536809000324
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H34 N4 O3 S 2+, 2I -, 2.5H2 O'
_chemical_formula_moiety         'C21 H34 N4 O3 S 2+, 2(I -), 2.5(H2 O)'
_chemical_formula_sum            'C21 H39 I2 N4 O5.5 S'
_chemical_formula_weight         721.43
_chemical_name_systematic
;Bis{(E)-3-[(Diethylmethylammonio)methyl]-N-[3-(N,N-
dimethylsulfamoyl)-1-methylpyridin-4-ylidene]-4-methoxyanilinium}
 tetraiodide
pentahydrate
;
_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           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                96.670(2)
_cell_angle_beta                 97.667(2)
_cell_angle_gamma                98.2240(10)
_cell_formula_units_Z            4
_cell_length_a                   12.7930(5)
_cell_length_b                   13.5539(6)
_cell_length_c                   16.8386(7)
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.84
_cell_measurement_theta_min      2.4
_cell_volume                     2836.5(2)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97  (Altomare et al.,  1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            49577
_diffrn_reflns_theta_full        26.4
_diffrn_reflns_theta_max         26.4
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    2.329
_exptl_absorpt_correction_T_max  0.830
_exptl_absorpt_correction_T_min  0.575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1436.0
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         2.071
_refine_diff_density_min         -1.416
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     654
_refine_ls_number_reflns         11468
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0429
_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)+(0.0655P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1155
_reflns_number_gt                8753
_reflns_number_total             11468
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg2227.cif
_cod_data_source_block           I
_cod_database_code               2220695
_cod_database_fobs_code          2220695
loop_
_space_group_symop_operation_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
O O1W 0.4474(3) 0.1184(3) 0.6544(2) 0.0347(10) Uani d D 1 . .
H H1WA 0.414(3) 0.172(2) 0.665(3) 0.042 Uiso d D 1 . .
H H1WB 0.5190(9) 0.135(3) 0.665(3) 0.042 Uiso d D 1 . .
O O2W 0.8769(5) 0.9278(3) 0.8610(3) 0.0587(14) Uani d D 1 . .
H H2WA 0.913(5) 0.940(4) 0.820(3) 0.070 Uiso d D 1 . .
H H2WB 0.836(5) 0.867(2) 0.852(3) 0.070 Uiso d D 1 . .
O O3W 0.2931(4) 0.9651(3) 0.6823(2) 0.0428(11) Uani d D 1 . .
H H3WA 0.352(3) 1.010(3) 0.681(3) 0.051 Uiso d D 1 . .
H H3WB 0.299(4) 0.931(4) 0.725(2) 0.051 Uiso d D 1 . .
O O4W 0.1157(4) 0.0625(4) 0.6565(3) 0.0485(12) Uani d D 1 . .
H H4WA 0.145(4) 0.1267(15) 0.655(4) 0.058 Uiso d D 1 . .
H H4WB 0.166(3) 0.026(3) 0.674(4) 0.058 Uiso d D 1 . .
O O5W 0.9315(4) 0.0196(4) 0.7284(3) 0.0555(13) Uani d D 1 . .
H H5WA 0.892(4) 0.065(4) 0.713(4) 0.067 Uiso d D 1 . .
H H5WB 0.989(3) 0.018(4) 0.703(3) 0.067 Uiso d D 1 . .
I I1 0.32351(3) 0.83284(3) 0.85134(2) 0.02456(10) Uani d . 1 . .
I I2 0.73146(3) 0.17740(3) 0.68619(2) 0.02986(11) Uani d . 1 . .
I I3 0.71949(3) 0.68226(3) 0.811724(17) 0.01851(10) Uani d . 1 . .
I I4 0.28842(3) 0.30343(3) 0.687434(18) 0.02097(10) Uani d . 1 . .
N N1 0.0320(3) 0.6774(3) 0.7703(2) 0.0179(9) Uani d . 1 . .
C C2 0.0149(4) 0.6876(4) 0.8477(2) 0.0171(11) Uani d . 1 . .
H H2 -0.0368 0.7251 0.8623 0.021 Uiso calc R 1 . .
C C3 0.0710(4) 0.6446(4) 0.9058(2) 0.0147(10) Uani d . 1 . .
C C4 0.1531(4) 0.5890(3) 0.8865(3) 0.0136(10) Uani d . 1 . .
C C5 0.1607(4) 0.5714(4) 0.8024(3) 0.0155(10) Uani d . 1 . .
H H5 0.2057 0.5282 0.7846 0.019 Uiso calc R 1 . .
C C6 0.1033(4) 0.6167(4) 0.7484(2) 0.0185(11) Uani d . 1 . .
H H6 0.1126 0.6064 0.6943 0.022 Uiso calc R 1 . .
C C7 -0.0207(4) 0.7323(4) 0.7111(3) 0.0278(13) Uani d . 1 . .
H H7A -0.0628 0.7754 0.7374 0.042 Uiso calc R 1 . .
H H7B -0.0662 0.6853 0.6693 0.042 Uiso calc R 1 . .
H H7C 0.0323 0.7722 0.6878 0.042 Uiso calc R 1 . .
S S8 0.03896(9) 0.67067(9) 1.00503(6) 0.0135(3) Uani d . 1 . .
O O9 0.0913(3) 0.6067(3) 1.05430(18) 0.0209(8) Uani d . 1 . .
O O10 -0.0746(3) 0.6639(3) 0.99700(18) 0.0204(8) Uani d . 1 . .
N N11 0.0902(3) 0.7864(3) 1.0408(2) 0.0175(9) Uani d . 1 . .
C C12 0.2061(4) 0.8092(5) 1.0648(3) 0.0321(14) Uani d . 1 . .
H H12A 0.2401 0.8128 1.0175 0.048 Uiso calc R 1 . .
H H12B 0.2299 0.7573 1.0934 0.048 Uiso calc R 1 . .
H H12C 0.2245 0.8726 1.0993 0.048 Uiso calc R 1 . .
C C13 0.0461(5) 0.8645(4) 0.9992(3) 0.0293(13) Uani d . 1 . .
H H13A 0.0769 0.8710 0.9508 0.044 Uiso calc R 1 . .
H H13B 0.0625 0.9276 1.0343 0.044 Uiso calc R 1 . .
H H13C -0.0301 0.8460 0.9855 0.044 Uiso calc R 1 . .
N N14 0.2167(3) 0.5534(3) 0.9424(2) 0.0146(9) Uani d D 1 . .
H H14 0.194(4) 0.561(3) 0.9901(14) 0.017 Uiso d D 1 . .
C C15 0.3067(4) 0.5053(3) 0.9282(2) 0.0134(10) Uani d . 1 . .
C C16 0.3822(4) 0.5466(3) 0.8849(2) 0.0116(10) Uani d . 1 . .
H H16 0.3753 0.6065 0.8643 0.014 Uiso calc R 1 . .
C C17 0.4682(4) 0.4985(4) 0.8721(2) 0.0141(10) Uani d . 1 . .
H H17 0.5191 0.5262 0.8429 0.017 Uiso calc R 1 . .
C C18 0.4789(4) 0.4094(4) 0.9026(2) 0.0134(10) Uani d . 1 . .
C C19 0.4046(4) 0.3688(3) 0.9500(2) 0.0131(10) Uani d . 1 . .
C C20 0.3190(4) 0.4191(4) 0.9622(2) 0.0135(10) Uani d . 1 . .
H H20 0.2696 0.3941 0.9936 0.016 Uiso calc R 1 . .
O O21 0.5609(3) 0.3568(2) 0.89193(18) 0.0156(7) Uani d . 1 . .
C C22 0.6274(4) 0.3884(4) 0.8348(3) 0.0284(13) Uani d . 1 . .
H H22A 0.5836 0.3918 0.7845 0.043 Uiso calc R 1 . .
H H22B 0.6751 0.3410 0.8261 0.043 Uiso calc R 1 . .
H H22C 0.6681 0.4536 0.8553 0.043 Uiso calc R 1 . .
C C23 0.4197(4) 0.2776(3) 0.9912(2) 0.0140(10) Uani d . 1 . .
H H23A 0.3960 0.2871 1.0436 0.017 Uiso calc R 1 . .
H H23B 0.4956 0.2745 1.0010 0.017 Uiso calc R 1 . .
N N24 0.3617(3) 0.1764(3) 0.9456(2) 0.0142(9) Uani d . 1 . .
C C25 0.4097(4) 0.1478(4) 0.8698(3) 0.0172(11) Uani d . 1 . .
H H25A 0.3627 0.0909 0.8369 0.021 Uiso calc R 1 . .
H H25B 0.4130 0.2037 0.8386 0.021 Uiso calc R 1 . .
C C26 0.5201(4) 0.1207(4) 0.8870(3) 0.0238(12) Uani d . 1 . .
H H26A 0.5641 0.1716 0.9267 0.036 Uiso calc R 1 . .
H H26B 0.5511 0.1162 0.8380 0.036 Uiso calc R 1 . .
H H26C 0.5154 0.0570 0.9071 0.036 Uiso calc R 1 . .
C C27 0.2446(4) 0.1837(4) 0.9202(3) 0.0199(11) Uani d . 1 . .
H H27A 0.2177 0.2154 0.9663 0.024 Uiso calc R 1 . .
H H27B 0.2399 0.2271 0.8784 0.024 Uiso calc R 1 . .
C C28 0.1728(4) 0.0841(4) 0.8887(3) 0.0295(13) Uani d . 1 . .
H H28A 0.2054 0.0462 0.8499 0.044 Uiso calc R 1 . .
H H28B 0.1049 0.0963 0.8635 0.044 Uiso calc R 1 . .
H H28C 0.1626 0.0468 0.9329 0.044 Uiso calc R 1 . .
C C29 0.3720(4) 0.1004(4) 1.0034(3) 0.0193(11) Uani d . 1 . .
H H29A 0.3495 0.0338 0.9745 0.029 Uiso calc R 1 . .
H H29B 0.3280 0.1116 1.0445 0.029 Uiso calc R 1 . .
H H29C 0.4452 0.1073 1.0283 0.029 Uiso calc R 1 . .
N N41 0.9817(3) 0.3632(3) 0.7359(2) 0.0143(9) Uani d . 1 . .
C C42 0.9073(4) 0.4212(4) 0.7574(2) 0.0150(11) Uani d . 1 . .
H H42 0.8988 0.4330 0.8115 0.018 Uiso calc R 1 . .
C C43 0.8464(4) 0.4612(4) 0.7019(3) 0.0140(10) Uani d . 1 . .
H H43 0.7975 0.5008 0.7185 0.017 Uiso calc R 1 . .
C C44 0.8558(4) 0.4437(3) 0.6181(2) 0.0118(10) Uani d . 1 . .
C C45 0.9372(4) 0.3870(3) 0.5991(2) 0.0113(10) Uani d . 1 . .
C C46 0.9962(4) 0.3490(3) 0.6584(3) 0.0135(10) Uani d . 1 . .
H H46 1.0484 0.3119 0.6445 0.016 Uiso calc R 1 . .
C C47 1.0393(4) 0.3134(4) 0.7974(3) 0.0226(12) Uani d . 1 . .
H H47A 0.9904 0.2617 0.8136 0.034 Uiso calc R 1 . .
H H47B 1.0703 0.3621 0.8436 0.034 Uiso calc R 1 . .
H H47C 1.0948 0.2840 0.7751 0.034 Uiso calc R 1 . .
S S48 0.95911(10) 0.34819(9) 0.49898(6) 0.0144(3) Uani d . 1 . .
O O49 0.9141(3) 0.4153(2) 0.44787(17) 0.0172(7) Uani d . 1 . .
O O50 1.0700(3) 0.3398(3) 0.50195(18) 0.0179(8) Uani d . 1 . .
N N51 0.8905(3) 0.2370(3) 0.4701(2) 0.0191(9) Uani d . 1 . .
C C52 0.9303(5) 0.1519(4) 0.5057(3) 0.0262(13) Uani d . 1 . .
H H52A 0.9004 0.1429 0.5542 0.039 Uiso calc R 1 . .
H H52B 1.0068 0.1660 0.5182 0.039 Uiso calc R 1 . .
H H52C 0.9093 0.0915 0.4676 0.039 Uiso calc R 1 . .
C C53 0.7730(4) 0.2294(4) 0.4602(3) 0.0265(13) Uani d . 1 . .
H H53A 0.7516 0.2823 0.4316 0.040 Uiso calc R 1 . .
H H53B 0.7505 0.2356 0.5125 0.040 Uiso calc R 1 . .
H H53C 0.7405 0.1653 0.4301 0.040 Uiso calc R 1 . .
N N54 0.7923(3) 0.4792(3) 0.5618(2) 0.0145(9) Uani d D 1 . .
H H54 0.813(4) 0.486(3) 0.5136(14) 0.017 Uiso d D 1 . .
C C55 0.6969(4) 0.5173(4) 0.5752(2) 0.0142(10) Uani d . 1 . .
C C56 0.6208(4) 0.4609(4) 0.6102(2) 0.0129(10) Uani d . 1 . .
H H56 0.6335 0.3998 0.6263 0.015 Uiso calc R 1 . .
C C57 0.5259(4) 0.4951(4) 0.6215(2) 0.0156(10) Uani d . 1 . .
H H57 0.4751 0.4571 0.6451 0.019 Uiso calc R 1 . .
C C58 0.5075(4) 0.5860(4) 0.5973(2) 0.0123(10) Uani d . 1 . .
C C59 0.5836(4) 0.6442(3) 0.5615(2) 0.0120(10) Uani d . 1 . .
C C60 0.6781(4) 0.6071(4) 0.5503(2) 0.0148(10) Uani d . 1 . .
H H60 0.7287 0.6438 0.5257 0.018 Uiso calc R 1 . .
O O61 0.4154(3) 0.6249(3) 0.60549(18) 0.0172(8) Uani d . 1 . .
C C62 0.3569(5) 0.5914(5) 0.6669(3) 0.0381(16) Uani d . 1 . .
H H62A 0.3151 0.5264 0.6473 0.057 Uiso calc R 1 . .
H H62B 0.3105 0.6385 0.6803 0.057 Uiso calc R 1 . .
H H62C 0.4060 0.5869 0.7143 0.057 Uiso calc R 1 . .
C C63 0.5599(4) 0.7401(3) 0.5315(2) 0.0154(10) Uani d . 1 . .
H H63A 0.4832 0.7341 0.5159 0.019 Uiso calc R 1 . .
H H63B 0.5925 0.7473 0.4833 0.019 Uiso calc R 1 . .
N N64 0.5981(3) 0.8360(3) 0.5915(2) 0.0162(9) Uani d . 1 . .
C C65 0.5493(4) 0.8250(4) 0.6690(3) 0.0182(11) Uani d . 1 . .
H H65A 0.4721 0.8108 0.6546 0.022 Uiso calc R 1 . .
H H65B 0.5718 0.7672 0.6912 0.022 Uiso calc R 1 . .
C C66 0.5774(4) 0.9148(4) 0.7346(3) 0.0221(12) Uani d . 1 . .
H H66A 0.6522 0.9236 0.7556 0.033 Uiso calc R 1 . .
H H66B 0.5363 0.9037 0.7774 0.033 Uiso calc R 1 . .
H H66C 0.5615 0.9740 0.7124 0.033 Uiso calc R 1 . .
C C67 0.7185(4) 0.8567(4) 0.6140(3) 0.0192(11) Uani d . 1 . .
H H67A 0.7416 0.7993 0.6366 0.023 Uiso calc R 1 . .
H H67B 0.7377 0.9144 0.6559 0.023 Uiso calc R 1 . .
C C68 0.7793(4) 0.8771(4) 0.5438(3) 0.0298(14) Uani d . 1 . .
H H68A 0.7636 0.8192 0.5030 0.045 Uiso calc R 1 . .
H H68B 0.8547 0.8907 0.5632 0.045 Uiso calc R 1 . .
H H68C 0.7578 0.9342 0.5212 0.045 Uiso calc R 1 . .
C C69 0.5592(4) 0.9205(4) 0.5531(3) 0.0244(12) Uani d . 1 . .
H H69A 0.5949 0.9835 0.5833 0.037 Uiso calc R 1 . .
H H69B 0.4835 0.9158 0.5528 0.037 Uiso calc R 1 . .
H H69C 0.5742 0.9167 0.4986 0.037 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 0 '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 0.006 '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'
I I -0.4742 1.8119 '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
H1WA O1W H1WB . . 112(4) ?
H2WA O2W H2WB . . 113(5) ?
H3WA O3W H3WB . . 111(4) ?
H4WA O4W H4WB . . 111(4) ?
H5WA O5W H5WB . . 113(5) ?
C2 N1 C6 . . 118.4(4) ?
C2 N1 C7 . . 121.3(4) ?
C6 N1 C7 . . 120.3(4) ?
N1 C2 C3 . . 122.2(4) ?
N1 C2 H2 . . 118.9 ?
C3 C2 H2 . . 118.9 ?
C2 C3 C4 . . 120.7(4) ?
C2 C3 S8 . . 115.0(3) ?
C4 C3 S8 . . 124.2(3) ?
N14 C4 C5 . . 122.1(4) ?
N14 C4 C3 . . 123.0(4) ?
C5 C4 C3 . . 114.9(4) ?
C6 C5 C4 . . 120.7(4) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 N1 . . 122.4(4) ?
C5 C6 H6 . . 118.8 ?
N1 C6 H6 . . 118.8 ?
N1 C7 H7A . . 109.5 ?
N1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
N1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O10 S8 O9 . . 119.4(2) ?
O10 S8 N11 . . 107.1(2) ?
O9 S8 N11 . . 107.6(2) ?
O10 S8 C3 . . 107.0(2) ?
O9 S8 C3 . . 107.0(2) ?
N11 S8 C3 . . 108.3(2) ?
C12 N11 C13 . . 113.2(4) ?
C12 N11 S8 . . 117.3(4) ?
C13 N11 S8 . . 116.3(3) ?
N11 C12 H12A . . 109.5 ?
N11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N11 C13 H13A . . 109.5 ?
N11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
N11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C4 N14 C15 . . 125.7(4) ?
C4 N14 H14 . . 110(3) ?
C15 N14 H14 . . 124(3) ?
C16 C15 C20 . . 120.5(4) ?
C16 C15 N14 . . 121.1(4) ?
C20 C15 N14 . . 118.4(4) ?
C15 C16 C17 . . 119.8(4) ?
C15 C16 H16 . . 120.1 ?
C17 C16 H16 . . 120.1 ?
C16 C17 C18 . . 120.3(4) ?
C16 C17 H17 . . 119.8 ?
C18 C17 H17 . . 119.8 ?
O21 C18 C17 . . 123.9(4) ?
O21 C18 C19 . . 115.8(4) ?
C17 C18 C19 . . 120.3(4) ?
C20 C19 C18 . . 118.0(4) ?
C20 C19 C23 . . 120.0(4) ?
C18 C19 C23 . . 121.8(4) ?
C15 C20 C19 . . 120.9(4) ?
C15 C20 H20 . . 119.5 ?
C19 C20 H20 . . 119.5 ?
C18 O21 C22 . . 116.3(4) ?
O21 C22 H22A . . 109.5 ?
O21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
O21 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C19 C23 N24 . . 116.0(4) ?
C19 C23 H23A . . 108.3 ?
N24 C23 H23A . . 108.3 ?
C19 C23 H23B . . 108.3 ?
N24 C23 H23B . . 108.3 ?
H23A C23 H23B . . 107.4 ?
C29 N24 C27 . . 110.4(4) ?
C29 N24 C25 . . 111.2(4) ?
C27 N24 C25 . . 108.3(3) ?
C29 N24 C23 . . 106.6(3) ?
C27 N24 C23 . . 109.3(3) ?
C25 N24 C23 . . 111.0(3) ?
C26 C25 N24 . . 113.8(4) ?
C26 C25 H25A . . 108.8 ?
N24 C25 H25A . . 108.8 ?
C26 C25 H25B . . 108.8 ?
N24 C25 H25B . . 108.8 ?
H25A C25 H25B . . 107.7 ?
C25 C26 H26A . . 109.5 ?
C25 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C25 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C28 C27 N24 . . 115.0(4) ?
C28 C27 H27A . . 108.5 ?
N24 C27 H27A . . 108.5 ?
C28 C27 H27B . . 108.5 ?
N24 C27 H27B . . 108.5 ?
H27A C27 H27B . . 107.5 ?
C27 C28 H28A . . 109.5 ?
C27 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C27 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
N24 C29 H29A . . 109.5 ?
N24 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
N24 C29 H29C . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
C46 N41 C42 . . 119.0(4) ?
C46 N41 C47 . . 121.3(4) ?
C42 N41 C47 . . 119.6(3) ?
C43 C42 N41 . . 121.6(4) ?
C43 C42 H42 . . 119.2 ?
N41 C42 H42 . . 119.2 ?
C42 C43 C44 . . 121.0(4) ?
C42 C43 H43 . . 119.5 ?
C44 C43 H43 . . 119.5 ?
N54 C44 C43 . . 121.6(4) ?
N54 C44 C45 . . 123.0(4) ?
C43 C44 C45 . . 115.4(4) ?
C46 C45 C44 . . 120.4(4) ?
C46 C45 S48 . . 115.1(3) ?
C44 C45 S48 . . 124.1(3) ?
N41 C46 C45 . . 122.4(4) ?
N41 C46 H46 . . 118.8 ?
C45 C46 H46 . . 118.8 ?
N41 C47 H47A . . 109.5 ?
N41 C47 H47B . . 109.5 ?
H47A C47 H47B . . 109.5 ?
N41 C47 H47C . . 109.5 ?
H47A C47 H47C . . 109.5 ?
H47B C47 H47C . . 109.5 ?
O50 S48 O49 . . 119.00(19) ?
O50 S48 N51 . . 107.7(2) ?
O49 S48 N51 . . 107.2(2) ?
O50 S48 C45 . . 107.9(2) ?
O49 S48 C45 . . 107.1(2) ?
N51 S48 C45 . . 107.4(2) ?
C53 N51 C52 . . 113.4(4) ?
C53 N51 S48 . . 116.5(3) ?
C52 N51 S48 . . 117.6(3) ?
N51 C52 H52A . . 109.5 ?
N51 C52 H52B . . 109.5 ?
H52A C52 H52B . . 109.5 ?
N51 C52 H52C . . 109.5 ?
H52A C52 H52C . . 109.5 ?
H52B C52 H52C . . 109.5 ?
N51 C53 H53A . . 109.5 ?
N51 C53 H53B . . 109.5 ?
H53A C53 H53B . . 109.5 ?
N51 C53 H53C . . 109.5 ?
H53A C53 H53C . . 109.5 ?
H53B C53 H53C . . 109.5 ?
C44 N54 C55 . . 124.6(4) ?
C44 N54 H54 . . 119(3) ?
C55 N54 H54 . . 116(3) ?
C60 C55 C56 . . 120.1(4) ?
C60 C55 N54 . . 120.4(4) ?
C56 C55 N54 . . 119.5(4) ?
C55 C56 C57 . . 120.5(4) ?
C55 C56 H56 . . 119.8 ?
C57 C56 H56 . . 119.8 ?
C58 C57 C56 . . 119.4(4) ?
C58 C57 H57 . . 120.3 ?
C56 C57 H57 . . 120.3 ?
O61 C58 C57 . . 123.2(4) ?
O61 C58 C59 . . 115.8(4) ?
C57 C58 C59 . . 120.9(4) ?
C60 C59 C58 . . 118.2(4) ?
C60 C59 C63 . . 121.4(4) ?
C58 C59 C63 . . 120.3(4) ?
C55 C60 C59 . . 120.9(4) ?
C55 C60 H60 . . 119.6 ?
C59 C60 H60 . . 119.6 ?
C58 O61 C62 . . 116.7(4) ?
O61 C62 H62A . . 109.5 ?
O61 C62 H62B . . 109.5 ?
H62A C62 H62B . . 109.5 ?
O61 C62 H62C . . 109.5 ?
H62A C62 H62C . . 109.5 ?
H62B C62 H62C . . 109.5 ?
C59 C63 N64 . . 115.6(4) ?
C59 C63 H63A . . 108.4 ?
N64 C63 H63A . . 108.4 ?
C59 C63 H63B . . 108.4 ?
N64 C63 H63B . . 108.4 ?
H63A C63 H63B . . 107.4 ?
C69 N64 C67 . . 110.6(4) ?
C69 N64 C63 . . 107.3(4) ?
C67 N64 C63 . . 112.2(3) ?
C69 N64 C65 . . 109.5(4) ?
C67 N64 C65 . . 108.2(3) ?
C63 N64 C65 . . 109.1(3) ?
C66 C65 N64 . . 116.0(4) ?
C66 C65 H65A . . 108.3 ?
N64 C65 H65A . . 108.3 ?
C66 C65 H65B . . 108.3 ?
N64 C65 H65B . . 108.3 ?
H65A C65 H65B . . 107.4 ?
C65 C66 H66A . . 109.5 ?
C65 C66 H66B . . 109.5 ?
H66A C66 H66B . . 109.5 ?
C65 C66 H66C . . 109.5 ?
H66A C66 H66C . . 109.5 ?
H66B C66 H66C . . 109.5 ?
N64 C67 C68 . . 114.7(4) ?
N64 C67 H67A . . 108.6 ?
C68 C67 H67A . . 108.6 ?
N64 C67 H67B . . 108.6 ?
C68 C67 H67B . . 108.6 ?
H67A C67 H67B . . 107.6 ?
C67 C68 H68A . . 109.5 ?
C67 C68 H68B . . 109.5 ?
H68A C68 H68B . . 109.5 ?
C67 C68 H68C . . 109.5 ?
H68A C68 H68C . . 109.5 ?
H68B C68 H68C . . 109.5 ?
N64 C69 H69A . . 109.5 ?
N64 C69 H69B . . 109.5 ?
H69A C69 H69B . . 109.5 ?
N64 C69 H69C . . 109.5 ?
H69A C69 H69C . . 109.5 ?
H69B C69 H69C . . 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
O1W H1WA . 0.90(6) ?
O1W H1WB . 0.90(2) ?
O2W H2WA . 0.90(6) ?
O2W H2WB . 0.89(5) ?
O3W H3WA . 0.89(4) ?
O3W H3WB . 0.90(3) ?
O4W H4WA . 0.90(4) ?
O4W H4WB . 0.90(3) ?
O5W H5WA . 0.89(4) ?
O5W H5WB . 0.89(5) ?
N1 C2 . 1.346(5) ?
N1 C6 . 1.371(6) ?
N1 C7 . 1.461(6) ?
C2 C3 . 1.369(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.428(6) ?
C3 S8 . 1.781(4) ?
C4 N14 . 1.339(6) ?
C4 C5 . 1.428(6) ?
C5 C6 . 1.351(7) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
S8 O10 . 1.430(3) ?
S8 O9 . 1.440(3) ?
S8 N11 . 1.622(4) ?
N11 C12 . 1.463(6) ?
N11 C13 . 1.473(6) ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
N14 C15 . 1.436(6) ?
N14 H14 . 0.89(6) ?
C15 C16 . 1.380(6) ?
C15 C20 . 1.378(6) ?
C16 C17 . 1.385(6) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.382(6) ?
C17 H17 . 0.9300 ?
C18 O21 . 1.369(5) ?
C18 C19 . 1.414(6) ?
C19 C20 . 1.396(6) ?
C19 C23 . 1.509(6) ?
C20 H20 . 0.9300 ?
O21 C22 . 1.429(5) ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
C23 N24 . 1.528(6) ?
C23 H23A . 0.9700 ?
C23 H23B . 0.9700 ?
N24 C29 . 1.505(6) ?
N24 C27 . 1.522(6) ?
N24 C25 . 1.523(5) ?
C25 C26 . 1.510(7) ?
C25 H25A . 0.9700 ?
C25 H25B . 0.9700 ?
C26 H26A . 0.9600 ?
C26 H26B . 0.9600 ?
C26 H26C . 0.9600 ?
C27 C28 . 1.514(7) ?
C27 H27A . 0.9700 ?
C27 H27B . 0.9700 ?
C28 H28A . 0.9600 ?
C28 H28B . 0.9600 ?
C28 H28C . 0.9600 ?
C29 H29A . 0.9600 ?
C29 H29B . 0.9600 ?
C29 H29C . 0.9600 ?
N41 C46 . 1.338(5) ?
N41 C42 . 1.377(6) ?
N41 C47 . 1.473(6) ?
C42 C43 . 1.349(7) ?
C42 H42 . 0.9300 ?
C43 C44 . 1.428(6) ?
C43 H43 . 0.9300 ?
C44 N54 . 1.342(6) ?
C44 C45 . 1.427(6) ?
C45 C46 . 1.365(6) ?
C45 S48 . 1.777(4) ?
C46 H46 . 0.9300 ?
C47 H47A . 0.9600 ?
C47 H47B . 0.9600 ?
C47 H47C . 0.9600 ?
S48 O50 . 1.434(3) ?
S48 O49 . 1.449(3) ?
S48 N51 . 1.617(4) ?
N51 C53 . 1.478(6) ?
N51 C52 . 1.482(6) ?
C52 H52A . 0.9600 ?
C52 H52B . 0.9600 ?
C52 H52C . 0.9600 ?
C53 H53A . 0.9600 ?
C53 H53B . 0.9600 ?
C53 H53C . 0.9600 ?
N54 C55 . 1.426(6) ?
N54 H54 . 0.90(6) ?
C55 C60 . 1.375(6) ?
C55 C56 . 1.388(6) ?
C56 C57 . 1.387(6) ?
C56 H56 . 0.9300 ?
C57 C58 . 1.383(6) ?
C57 H57 . 0.9300 ?
C58 O61 . 1.375(5) ?
C58 C59 . 1.407(6) ?
C59 C60 . 1.401(6) ?
C59 C63 . 1.504(6) ?
C60 H60 . 0.9300 ?
O61 C62 . 1.433(5) ?
C62 H62A . 0.9600 ?
C62 H62B . 0.9600 ?
C62 H62C . 0.9600 ?
C63 N64 . 1.526(6) ?
C63 H63A . 0.9700 ?
C63 H63B . 0.9700 ?
N64 C69 . 1.493(6) ?
N64 C67 . 1.513(6) ?
N64 C65 . 1.534(5) ?
C65 C66 . 1.511(6) ?
C65 H65A . 0.9700 ?
C65 H65B . 0.9700 ?
C66 H66A . 0.9600 ?
C66 H66B . 0.9600 ?
C66 H66C . 0.9600 ?
C67 C68 . 1.529(6) ?
C67 H67A . 0.9700 ?
C67 H67B . 0.9700 ?
C68 H68A . 0.9600 ?
C68 H68B . 0.9600 ?
C68 H68C . 0.9600 ?
C69 H69A . 0.9600 ?
C69 H69B . 0.9600 ?
C69 H69C . 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
O1W H1WA I4 1_555 0.91(3) 2.60(4) 3.489(4) 170(3) yes
O1W H1WB I2 1_555 0.90(2) 2.663(17) 3.561(4) 176(4) yes
O2W H2WA O5w 1_565 0.90(4) 1.98(5) 2.799(7) 147(5) yes
O2W H2WB I3 1_555 0.90(4) 2.69(4) 3.580(5) 175(4) yes
O3W H3WA O1W 1_565 0.90(4) 1.91(4) 2.781(6) 161(18) yes
O3W H3WB I1 1_555 0.90(4) 2.64(4) 3.544(4) 178(5) yes
O4W H4WA I4 1_555 0.90(3) 2.75(3) 3.613(5) 160(4) yes
O4W H4WB O3W 1_545 0.89(5) 1.92(4) 2.795(7) 162(2) yes
O5W H5WA I2 1_555 0.90(4) 2.75(5) 3.614(5) 165(4) yes
O5W H5WB O4w 1_655 0.90(4) 1.94(4) 2.809(7) 161(3) yes
N14 H14 O9 1_555 0.90(3) 1.93(4) 2.733(5) 149(4) yes
N54 H54 O49 1_555 0.90(5) 2.08(4) 2.767(5) 133(4) yes
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
C6 N1 C2 C3 . . . . 4.1(7) ?
C7 N1 C2 C3 . . . . -173.6(5) ?
N1 C2 C3 C4 . . . . 1.9(8) ?
N1 C2 C3 S8 . . . . 178.1(4) ?
C2 C3 C4 N14 . . . . 173.7(5) ?
S8 C3 C4 N14 . . . . -2.2(7) ?
C2 C3 C4 C5 . . . . -8.0(7) ?
S8 C3 C4 C5 . . . . 176.2(4) ?
N14 C4 C5 C6 . . . . -173.1(5) ?
C3 C4 C5 C6 . . . . 8.5(7) ?
C4 C5 C6 N1 . . . . -3.1(8) ?
C2 N1 C6 C5 . . . . -3.5(7) ?
C7 N1 C6 C5 . . . . 174.2(5) ?
C2 C3 S8 O10 . . . . 41.5(4) ?
C4 C3 S8 O10 . . . . -142.5(4) ?
C2 C3 S8 O9 . . . . 170.5(4) ?
C4 C3 S8 O9 . . . . -13.4(5) ?
C2 C3 S8 N11 . . . . -73.7(4) ?
C4 C3 S8 N11 . . . . 102.4(4) ?
O10 S8 N11 C12 . . . . 171.9(3) ?
O9 S8 N11 C12 . . . . 42.4(4) ?
C3 S8 N11 C12 . . . . -73.1(4) ?
O10 S8 N11 C13 . . . . -49.7(4) ?
O9 S8 N11 C13 . . . . -179.2(3) ?
C3 S8 N11 C13 . . . . 65.4(4) ?
C5 C4 N14 C15 . . . . 7.9(7) ?
C3 C4 N14 C15 . . . . -173.8(4) ?
C4 N14 C15 C16 . . . . 47.5(7) ?
C4 N14 C15 C20 . . . . -135.6(5) ?
C20 C15 C16 C17 . . . . 3.1(7) ?
N14 C15 C16 C17 . . . . -180.0(4) ?
C15 C16 C17 C18 . . . . -0.1(7) ?
C16 C17 C18 O21 . . . . 179.3(4) ?
C16 C17 C18 C19 . . . . -2.7(7) ?
O21 C18 C19 C20 . . . . -179.5(4) ?
C17 C18 C19 C20 . . . . 2.4(7) ?
O21 C18 C19 C23 . . . . 4.4(6) ?
C17 C18 C19 C23 . . . . -173.7(4) ?
C16 C15 C20 C19 . . . . -3.4(7) ?
N14 C15 C20 C19 . . . . 179.6(4) ?
C18 C19 C20 C15 . . . . 0.7(7) ?
C23 C19 C20 C15 . . . . 176.8(4) ?
C17 C18 O21 C22 . . . . -10.8(6) ?
C19 C18 O21 C22 . . . . 171.1(4) ?
C20 C19 C23 N24 . . . . 88.3(5) ?
C18 C19 C23 N24 . . . . -95.7(5) ?
C19 C23 N24 C29 . . . . -170.2(4) ?
C19 C23 N24 C27 . . . . -50.9(5) ?
C19 C23 N24 C25 . . . . 68.5(5) ?
C29 N24 C25 C26 . . . . -48.6(5) ?
C27 N24 C25 C26 . . . . -170.1(4) ?
C23 N24 C25 C26 . . . . 69.9(5) ?
C29 N24 C27 C28 . . . . -51.8(5) ?
C25 N24 C27 C28 . . . . 70.2(5) ?
C23 N24 C27 C28 . . . . -168.7(4) ?
C46 N41 C42 C43 . . . . 2.2(7) ?
C47 N41 C42 C43 . . . . -174.4(5) ?
N41 C42 C43 C44 . . . . 0.9(7) ?
C42 C43 C44 N54 . . . . 176.9(5) ?
C42 C43 C44 C45 . . . . -3.6(7) ?
N54 C44 C45 C46 . . . . -177.1(4) ?
C43 C44 C45 C46 . . . . 3.4(7) ?
N54 C44 C45 S48 . . . . -4.7(7) ?
C43 C44 C45 S48 . . . . 175.7(3) ?
C42 N41 C46 C45 . . . . -2.4(7) ?
C47 N41 C46 C45 . . . . 174.2(5) ?
C44 C45 C46 N41 . . . . -0.5(7) ?
S48 C45 C46 N41 . . . . -173.5(4) ?
C46 C45 S48 O50 . . . . -35.4(4) ?
C44 C45 S48 O50 . . . . 151.9(4) ?
C46 C45 S48 O49 . . . . -164.7(4) ?
C44 C45 S48 O49 . . . . 22.6(5) ?
C46 C45 S48 N51 . . . . 80.4(4) ?
C44 C45 S48 N51 . . . . -92.3(4) ?
O50 S48 N51 C53 . . . . -177.9(3) ?
O49 S48 N51 C53 . . . . -48.7(4) ?
C45 S48 N51 C53 . . . . 66.1(4) ?
O50 S48 N51 C52 . . . . 42.5(4) ?
O49 S48 N51 C52 . . . . 171.7(3) ?
C45 S48 N51 C52 . . . . -73.4(4) ?
C43 C44 N54 C55 . . . . -14.1(7) ?
C45 C44 N54 C55 . . . . 166.3(4) ?
C44 N54 C55 C60 . . . . 132.6(5) ?
C44 N54 C55 C56 . . . . -50.3(6) ?
C60 C55 C56 C57 . . . . -0.9(7) ?
N54 C55 C56 C57 . . . . -178.0(4) ?
C55 C56 C57 C58 . . . . 0.1(6) ?
C56 C57 C58 O61 . . . . 179.3(4) ?
C56 C57 C58 C59 . . . . 0.0(6) ?
O61 C58 C59 C60 . . . . -178.8(4) ?
C57 C58 C59 C60 . . . . 0.6(6) ?
O61 C58 C59 C63 . . . . -2.7(6) ?
C57 C58 C59 C63 . . . . 176.7(4) ?
C56 C55 C60 C59 . . . . 1.5(7) ?
N54 C55 C60 C59 . . . . 178.6(4) ?
C58 C59 C60 C55 . . . . -1.3(6) ?
C63 C59 C60 C55 . . . . -177.4(4) ?
C57 C58 O61 C62 . . . . 24.1(6) ?
C59 C58 O61 C62 . . . . -156.6(4) ?
C60 C59 C63 N64 . . . . -90.8(5) ?
C58 C59 C63 N64 . . . . 93.3(5) ?
C59 C63 N64 C69 . . . . -175.4(4) ?
C59 C63 N64 C67 . . . . 63.0(5) ?
C59 C63 N64 C65 . . . . -56.9(5) ?
C69 N64 C65 C66 . . . . -61.7(5) ?
C67 N64 C65 C66 . . . . 58.9(5) ?
C63 N64 C65 C66 . . . . -178.8(4) ?
C69 N64 C67 C68 . . . . -56.0(5) ?
C63 N64 C67 C68 . . . . 63.7(5) ?
C65 N64 C67 C68 . . . . -175.8(4) ?
