#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/16/2221685.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_2221685
loop_
_publ_author_name
'Bartolucci, Gianluca'
'Bruni, Bruno'
'Coran, Silvia A.'
'Di Vaira, Massimo'
_publ_section_title
;4-(3-Methylanilino)-N-[N-(1-methylethyl)carbamoyl]pyridinium-3-sulfonamidate
 (torasemide) methanol 0.25-solvate 0.25-hydrate
;
_journal_coeditor_code           HB2934
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o970
_journal_page_last               o971
_journal_paper_doi               10.1107/S160053680901160X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H20 N4 O3 S1, 0.25C H4 O, 0.25H2 O'
_chemical_formula_moiety         'C16 H20 N4 O3 S1, 0.25(C H4 O), 0.25(H2 O)'
_chemical_formula_sum            'C65 H86 N16 O14 S4'
_chemical_formula_weight         360.94
_chemical_name_common
'torasemide methanol 0.25-solvate 0.25-hydrate'
_chemical_name_systematic
;
4-(3-Methylanilino)-N-[N-(1-methylethyl)carbamoyl]pyridinium-\
3-sulfonamidate methanol 0.25-solvate 0.25-hydrate
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 108.6460(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.8477(2)
_cell_length_b                   11.59510(10)
_cell_length_c                   20.3256(2)
_cell_measurement_reflns_used    37208
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      72.43
_cell_measurement_theta_min      4.12
_cell_volume                     3762.21(7)
_computing_cell_refinement       'CrysAlisPro CCD (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlisPro CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlisPro RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999) and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.1241
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur PX Ultra CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Oxford Diffraction Enhance ULTRA assembly'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            50677
_diffrn_reflns_theta_full        72.86
_diffrn_reflns_theta_max         72.86
_diffrn_reflns_theta_min         4.12
_exptl_absorpt_coefficient_mu    1.744
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSPACK; Oxford Diffraction, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.947
_refine_diff_density_min         -0.567
_refine_ls_extinction_coef       0.00135(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     496
_refine_ls_number_reflns         7402
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0520
_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)+(0.0978P)²+2.03P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1526
_refine_ls_wR_factor_ref         0.1559
_reflns_number_gt                6976
_reflns_number_total             7402
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2934.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 2/n'
_cod_database_code               2221685
_cod_database_fobs_code          2221685
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, 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
C C1 0.19533(12) 0.48508(17) -0.00966(10) 0.0373(4) Uani d . 1 . .
C C2 0.27341(13) 0.43982(19) -0.01066(12) 0.0437(5) Uani d . 1 . .
H H2 0.2910 0.3659 0.0087 0.052 Uiso calc R 1 . .
C C3 0.32285(14) 0.5010(2) -0.03890(12) 0.0485(5) Uani d . 1 . .
H H3 0.3756 0.4706 -0.0379 0.058 Uiso calc R 1 . .
N N2 0.29823(12) 0.60467(17) -0.06847(10) 0.0459(4) Uani d . 1 . .
H H2N 0.3334(18) 0.643(2) -0.0811(15) 0.055 Uiso d . 1 . .
C C4 0.22400(13) 0.64928(19) -0.07146(11) 0.0420(4) Uani d . 1 . .
H H4 0.2076 0.7215 -0.0937 0.050 Uiso calc R 1 . .
C C5 0.17111(12) 0.59364(17) -0.04330(10) 0.0369(4) Uani d . 1 . .
S S1 0.07610(3) 0.66425(4) -0.04649(2) 0.03510(15) Uani d . 1 . .
O O1 0.08434(9) 0.69312(13) 0.02476(7) 0.0404(3) Uani d . 1 . .
O O2 0.06917(10) 0.76225(12) -0.09190(8) 0.0426(3) Uani d . 1 . .
N N3 0.00665(10) 0.56968(14) -0.07018(8) 0.0357(3) Uani d . 1 . .
C C6 -0.00564(12) 0.51828(17) -0.13380(10) 0.0365(4) Uani d . 1 . .
O O3 0.02024(10) 0.55425(13) -0.18126(8) 0.0460(4) Uani d . 1 . .
N N4 -0.04911(12) 0.41930(16) -0.14092(9) 0.0445(4) Uani d . 1 . .
H H4N -0.0622(17) 0.389(2) -0.1047(15) 0.053 Uiso d . 1 . .
C C7 -0.05800(17) 0.3402(2) -0.19833(12) 0.0533(6) Uani d . 1 . .
H H7 -0.0722 0.3856 -0.2424 0.064 Uiso calc R 1 . .
C C8 -0.1274(2) 0.2567(3) -0.20331(17) 0.0795(10) Uani d . 1 . .
H H81 -0.1136 0.2106 -0.1607 0.119 Uiso calc R 1 . .
H H82 -0.1346 0.2058 -0.2433 0.119 Uiso calc R 1 . .
H H83 -0.1795 0.2992 -0.2092 0.119 Uiso calc R 1 . .
C C9 0.0240(2) 0.2749(3) -0.1887(2) 0.0837(10) Uani d . 1 . .
H H91 0.0699 0.3303 -0.1823 0.126 Uiso calc R 1 . .
H H92 0.0186 0.2277 -0.2299 0.126 Uiso calc R 1 . .
H H93 0.0361 0.2251 -0.1477 0.126 Uiso calc R 1 . .
N N1 0.14707(11) 0.42831(15) 0.02100(10) 0.0403(4) Uani d . 1 . .
H H1N 0.0987(18) 0.452(2) 0.0161(14) 0.048 Uiso d . 1 . .
C C10 0.17350(13) 0.32972(18) 0.06475(11) 0.0404(4) Uani d . 1 . .
C C11 0.12689(15) 0.23004(18) 0.04998(12) 0.0445(5) Uani d . 1 . .
H H11 0.0792 0.2260 0.0095 0.053 Uiso calc R 1 . .
C C12 0.14906(17) 0.1347(2) 0.09404(14) 0.0527(6) Uani d . 1 . .
C C13 0.21970(18) 0.1432(2) 0.15223(14) 0.0602(7) Uani d . 1 . .
H H13 0.2363 0.0787 0.1824 0.072 Uiso calc R 1 . .
C C14 0.26604(18) 0.2426(3) 0.16715(15) 0.0632(7) Uani d . 1 . .
H H14 0.3140 0.2464 0.2074 0.076 Uiso calc R 1 . .
C C15 0.24336(16) 0.3373(2) 0.12404(13) 0.0542(6) Uani d . 1 . .
H H15 0.2750 0.4066 0.1347 0.065 Uiso calc R 1 . .
C C16 0.0971(2) 0.0273(2) 0.07844(19) 0.0770(9) Uani d . 1 . .
H H161 0.1053 -0.0119 0.0384 0.116 Uiso calc R 1 . .
H H162 0.0378 0.0474 0.0679 0.116 Uiso calc R 1 . .
H H163 0.1141 -0.0241 0.1188 0.116 Uiso calc R 1 . .
C C17 0.46551(12) 0.07450(16) 0.14989(10) 0.0361(4) Uani d . 1 . .
C C18 0.45704(14) 0.05823(19) 0.21650(10) 0.0427(5) Uani d . 1 . .
H H18 0.4363 -0.0129 0.2275 0.051 Uiso calc R 1 . .
C C19 0.47838(14) 0.14364(19) 0.26474(11) 0.0437(5) Uani d . 1 . .
H H19 0.4733 0.1307 0.3094 0.052 Uiso calc R 1 . .
N N6 0.50654(12) 0.24638(16) 0.25054(9) 0.0418(4) Uani d . 1 . .
H H6N 0.5204(16) 0.304(2) 0.2829(14) 0.050 Uiso d . 1 . .
C C20 0.51362(13) 0.26759(17) 0.18762(11) 0.0381(4) Uani d . 1 . .
H H20 0.5332 0.3408 0.1785 0.046 Uiso calc R 1 . .
C C21 0.49306(12) 0.18543(16) 0.13642(10) 0.0344(4) Uani d . 1 . .
S S2 0.50042(3) 0.21861(4) 0.05304(2) 0.03520(15) Uani d . 1 . .
O O5 0.53461(10) 0.33358(12) 0.05809(8) 0.0430(3) Uani d . 1 . .
O O4 0.41666(9) 0.20622(13) 0.00468(8) 0.0438(3) Uani d . 1 . .
N N7 0.55423(10) 0.11763(14) 0.03788(8) 0.0360(3) Uani d . 1 . .
C C22 0.63508(13) 0.10566(17) 0.08225(10) 0.0373(4) Uani d . 1 . .
O O6 0.67497(9) 0.18090(13) 0.12360(7) 0.0432(3) Uani d . 1 . .
N N8 0.66900(14) 0.00256(19) 0.07774(11) 0.0555(5) Uani d . 1 . .
H H8N 0.636(2) -0.047(3) 0.0531(17) 0.067 Uiso d . 1 . .
C C23 0.75356(18) -0.0308(3) 0.11811(16) 0.0696(8) Uani d . 1 . .
H H23 0.7776 0.0268 0.1559 0.084 Uiso calc R 1 . .
C C24 0.7492(3) -0.1528(5) 0.1507(3) 0.134(2) Uani d . 1 . .
H H241 0.7311 -0.1440 0.1917 0.201 Uiso calc R 1 . .
H H242 0.8046 -0.1890 0.1642 0.201 Uiso calc R 1 . .
H H243 0.7089 -0.2015 0.1164 0.201 Uiso calc R 1 . .
C C25 0.8076(3) -0.0405(5) 0.0741(3) 0.128(2) Uani d . 1 . .
H H251 0.7865 -0.1020 0.0398 0.192 Uiso calc R 1 . .
H H252 0.8649 -0.0588 0.1031 0.192 Uiso calc R 1 . .
H H253 0.8074 0.0328 0.0500 0.192 Uiso calc R 1 . .
N N5 0.45039(12) -0.01004(14) 0.10282(9) 0.0404(4) Uani d . 1 . .
H H5N 0.4718(16) -0.004(2) 0.0697(14) 0.048 Uiso d . 1 . .
C C26 0.41125(13) -0.11707(16) 0.10831(10) 0.0370(4) Uani d . 1 . .
C C27 0.45708(15) -0.21778(18) 0.11739(11) 0.0426(5) Uani d . 1 . .
H H27 0.5151 -0.2154 0.1226 0.051 Uiso calc R 1 . .
C C28 0.41752(17) -0.32354(19) 0.11896(11) 0.0497(5) Uani d . 1 . .
C C29 0.33272(17) -0.3224(2) 0.11144(12) 0.0525(6) Uani d . 1 . .
H H29 0.3052 -0.3934 0.1131 0.063 Uiso calc R 1 . .
C C30 0.28749(16) -0.2224(2) 0.10169(13) 0.0521(6) Uani d . 1 . .
H H30 0.2293 -0.2246 0.0959 0.063 Uiso calc R 1 . .
C C31 0.32645(14) -0.11830(19) 0.10030(11) 0.0440(5) Uani d . 1 . .
H H31 0.2956 -0.0483 0.0939 0.053 Uiso calc R 1 . .
C C32 0.4664(2) -0.4336(2) 0.12887(16) 0.0704(8) Uani d . 1 . .
H H321 0.4287 -0.4990 0.1264 0.106 Uiso calc R 1 . .
H H322 0.5100 -0.4328 0.1744 0.106 Uiso calc R 1 . .
H H323 0.4925 -0.4410 0.0923 0.106 Uiso calc R 1 . .
O O8 0.7099(4) 0.2571(5) 0.2572(2) 0.0972(18) Uani d PD 0.50 . .
H H81O 0.740(6) 0.221(10) 0.284(4) 0.146 Uiso d PD 0.50 . .
H H82O 0.706(7) 0.228(10) 0.223(4) 0.146 Uiso d PD 0.50 . .
O O7 0.6701(3) 0.4556(5) 0.2137(3) 0.0920(14) Uani d PD 0.50 . .
H H7O 0.679(6) 0.397(2) 0.2459(11) 0.138 Uiso d PD 0.50 . .
C C33 0.7049(4) 0.5514(6) 0.2484(5) 0.087(2) Uani d PD 0.50 . .
H H331 0.6809 0.5664 0.2856 0.131 Uiso calc PR 0.50 . .
H H332 0.6935 0.6171 0.2164 0.131 Uiso calc PR 0.50 . .
H H333 0.7656 0.5405 0.2685 0.131 Uiso calc PR 0.50 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
N1 C1 C2 . . 121.69(19) ?
N1 C1 C5 . . 122.07(18) ?
C2 C1 C5 . . 116.25(18) ?
C3 C2 C1 . . 120.7(2) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
N2 C3 C2 . . 120.9(2) ?
N2 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
C4 N2 C3 . . 121.00(19) ?
C4 N2 H2N . . 121(2) ?
C3 N2 H2N . . 117.2(19) ?
N2 C4 C5 . . 121.6(2) ?
N2 C4 H4 . . 119.2 ?
C5 C4 H4 . . 119.2 ?
C4 C5 C1 . . 119.49(19) ?
C4 C5 S1 . . 117.85(16) ?
C1 C5 S1 . . 122.59(15) ?
O2 S1 O1 . . 114.78(9) ?
O2 S1 N3 . . 117.08(9) ?
O1 S1 N3 . . 107.04(9) ?
O2 S1 C5 . . 105.84(9) ?
O1 S1 C5 . . 105.79(9) ?
N3 S1 C5 . . 105.32(9) ?
C6 N3 S1 . . 117.75(14) ?
O3 C6 N4 . . 120.94(19) ?
O3 C6 N3 . . 126.50(19) ?
N4 C6 N3 . . 112.55(17) ?
C6 N4 C7 . . 122.53(18) ?
C6 N4 H4N . . 120.4(18) ?
C7 N4 H4N . . 115.1(18) ?
N4 C7 C8 . . 109.9(2) ?
N4 C7 C9 . . 110.6(2) ?
C8 C7 C9 . . 110.0(3) ?
N4 C7 H7 . . 108.8 ?
C8 C7 H7 . . 108.8 ?
C9 C7 H7 . . 108.8 ?
C7 C8 H81 . . 109.5 ?
C7 C8 H82 . . 109.5 ?
H81 C8 H82 . . 109.5 ?
C7 C8 H83 . . 109.5 ?
H81 C8 H83 . . 109.5 ?
H82 C8 H83 . . 109.5 ?
C7 C9 H91 . . 109.5 ?
C7 C9 H92 . . 109.5 ?
H91 C9 H92 . . 109.5 ?
C7 C9 H93 . . 109.5 ?
H91 C9 H93 . . 109.5 ?
H92 C9 H93 . . 109.5 ?
C1 N1 C10 . . 124.46(18) ?
C1 N1 H1N . . 119.7(19) ?
C10 N1 H1N . . 115.8(19) ?
C11 C10 C15 . . 120.5(2) ?
C11 C10 N1 . . 119.59(19) ?
C15 C10 N1 . . 119.82(19) ?
C10 C11 C12 . . 120.5(2) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C13 C12 C11 . . 118.2(2) ?
C13 C12 C16 . . 121.5(2) ?
C11 C12 C16 . . 120.3(3) ?
C14 C13 C12 . . 121.4(2) ?
C14 C13 H13 . . 119.3 ?
C12 C13 H13 . . 119.3 ?
C13 C14 C15 . . 120.4(3) ?
C13 C14 H14 . . 119.8 ?
C15 C14 H14 . . 119.8 ?
C14 C15 C10 . . 119.1(2) ?
C14 C15 H15 . . 120.5 ?
C10 C15 H15 . . 120.5 ?
C12 C16 H161 . . 109.5 ?
C12 C16 H162 . . 109.5 ?
H161 C16 H162 . . 109.5 ?
C12 C16 H163 . . 109.5 ?
H161 C16 H163 . . 109.5 ?
H162 C16 H163 . . 109.5 ?
N5 C17 C18 . . 122.11(18) ?
N5 C17 C21 . . 121.63(17) ?
C18 C17 C21 . . 116.25(17) ?
C19 C18 C17 . . 120.50(19) ?
C19 C18 H18 . . 119.7 ?
C17 C18 H18 . . 119.7 ?
N6 C19 C18 . . 121.33(19) ?
N6 C19 H19 . . 119.3 ?
C18 C19 H19 . . 119.3 ?
C20 N6 C19 . . 120.66(18) ?
C20 N6 H6N . . 117.9(17) ?
C19 N6 H6N . . 121.4(17) ?
N6 C20 C21 . . 121.13(19) ?
N6 C20 H20 . . 119.4 ?
C21 C20 H20 . . 119.4 ?
C20 C21 C17 . . 120.05(18) ?
C20 C21 S2 . . 119.65(15) ?
C17 C21 S2 . . 120.30(14) ?
O5 S2 O4 . . 114.89(9) ?
O5 S2 N7 . . 117.42(9) ?
O4 S2 N7 . . 106.96(9) ?
O5 S2 C21 . . 106.24(9) ?
O4 S2 C21 . . 106.00(9) ?
N7 S2 C21 . . 104.24(9) ?
C22 N7 S2 . . 117.27(13) ?
O6 C22 N8 . . 121.3(2) ?
O6 C22 N7 . . 125.21(18) ?
N8 C22 N7 . . 113.48(18) ?
C22 N8 C23 . . 124.2(2) ?
C22 N8 H8N . . 116(2) ?
C23 N8 H8N . . 119(2) ?
N8 C23 C25 . . 111.3(3) ?
N8 C23 C24 . . 107.9(3) ?
C25 C23 C24 . . 108.0(4) ?
N8 C23 H23 . . 109.9 ?
C25 C23 H23 . . 109.9 ?
C24 C23 H23 . . 109.9 ?
C23 C24 H241 . . 109.5 ?
C23 C24 H242 . . 109.5 ?
H241 C24 H242 . . 109.5 ?
C23 C24 H243 . . 109.5 ?
H241 C24 H243 . . 109.5 ?
H242 C24 H243 . . 109.5 ?
C23 C25 H251 . . 109.5 ?
C23 C25 H252 . . 109.5 ?
H251 C25 H252 . . 109.5 ?
C23 C25 H253 . . 109.5 ?
H251 C25 H253 . . 109.5 ?
H252 C25 H253 . . 109.5 ?
C17 N5 C26 . . 124.70(17) ?
C17 N5 H5N . . 117.8(18) ?
C26 N5 H5N . . 116.9(18) ?
C27 C26 C31 . . 121.27(19) ?
C27 C26 N5 . . 119.60(19) ?
C31 C26 N5 . . 119.01(19) ?
C26 C27 C28 . . 119.6(2) ?
C26 C27 H27 . . 120.2 ?
C28 C27 H27 . . 120.2 ?
C29 C28 C27 . . 118.0(2) ?
C29 C28 C32 . . 121.7(2) ?
C27 C28 C32 . . 120.3(2) ?
C30 C29 C28 . . 122.0(2) ?
C30 C29 H29 . . 119.0 ?
C28 C29 H29 . . 119.0 ?
C29 C30 C31 . . 119.9(2) ?
C29 C30 H30 . . 120.0 ?
C31 C30 H30 . . 120.0 ?
C30 C31 C26 . . 119.1(2) ?
C30 C31 H31 . . 120.4 ?
C26 C31 H31 . . 120.4 ?
C28 C32 H321 . . 109.5 ?
C28 C32 H322 . . 109.5 ?
H321 C32 H322 . . 109.5 ?
C28 C32 H323 . . 109.5 ?
H321 C32 H323 . . 109.5 ?
H322 C32 H323 . . 109.5 ?
H81O O8 H82O . . 105.0(10) ?
C33 O7 H7O . . 107.0(7) ?
O7 C33 H331 . . 109.5 ?
O7 C33 H332 . . 109.5 ?
H331 C33 H332 . . 109.5 ?
O7 C33 H333 . . 109.5 ?
H331 C33 H333 . . 109.5 ?
H332 C33 H333 . . 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
C1 N1 . 1.344(3) ?
C1 C2 . 1.422(3) ?
C1 C5 . 1.428(3) ?
C2 C3 . 1.354(3) ?
C2 H2 . 0.9500 ?
C3 N2 . 1.348(3) ?
C3 H3 . 0.9500 ?
N2 C4 . 1.337(3) ?
N2 H2N . 0.84(3) ?
C4 C5 . 1.365(3) ?
C4 H4 . 0.9500 ?
C5 S1 . 1.781(2) ?
S1 O2 . 1.4449(14) ?
S1 O1 . 1.4491(14) ?
S1 N3 . 1.5630(17) ?
N3 C6 . 1.378(3) ?
C6 O3 . 1.250(2) ?
C6 N4 . 1.344(3) ?
N4 C7 . 1.454(3) ?
N4 H4N . 0.90(3) ?
C7 C8 . 1.496(4) ?
C7 C9 . 1.533(4) ?
C7 H7 . 1.0000 ?
C8 H81 . 0.9800 ?
C8 H82 . 0.9800 ?
C8 H83 . 0.9800 ?
C9 H91 . 0.9800 ?
C9 H92 . 0.9800 ?
C9 H93 . 0.9800 ?
N1 C10 . 1.429(3) ?
N1 H1N . 0.83(3) ?
C10 C11 . 1.375(3) ?
C10 C15 . 1.392(3) ?
C11 C12 . 1.396(3) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.387(4) ?
C12 C16 . 1.498(4) ?
C13 C14 . 1.371(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.380(4) ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
C16 H161 . 0.9800 ?
C16 H162 . 0.9800 ?
C16 H163 . 0.9800 ?
C17 N5 . 1.336(2) ?
C17 C18 . 1.419(3) ?
C17 C21 . 1.423(3) ?
C18 C19 . 1.359(3) ?
C18 H18 . 0.9500 ?
C19 N6 . 1.347(3) ?
C19 H19 . 0.9500 ?
N6 C20 . 1.345(3) ?
N6 H6N . 0.92(3) ?
C20 C21 . 1.371(3) ?
C20 H20 . 0.9500 ?
C21 S2 . 1.781(2) ?
S2 O5 . 1.4428(14) ?
S2 O4 . 1.4462(15) ?
S2 N7 . 1.5704(16) ?
N7 C22 . 1.379(3) ?
C22 O6 . 1.248(2) ?
C22 N8 . 1.341(3) ?
N8 C23 . 1.451(3) ?
N8 H8N . 0.85(3) ?
C23 C25 . 1.471(5) ?
C23 C24 . 1.574(6) ?
C23 H23 . 1.0000 ?
C24 H241 . 0.9800 ?
C24 H242 . 0.9800 ?
C24 H243 . 0.9800 ?
C25 H251 . 0.9800 ?
C25 H252 . 0.9800 ?
C25 H253 . 0.9800 ?
N5 C26 . 1.426(2) ?
N5 H5N . 0.86(3) ?
C26 C27 . 1.379(3) ?
C26 C31 . 1.385(3) ?
C27 C28 . 1.401(3) ?
C27 H27 . 0.9500 ?
C28 C29 . 1.387(4) ?
C28 C32 . 1.497(3) ?
C29 C30 . 1.367(4) ?
C29 H29 . 0.9500 ?
C30 C31 . 1.379(3) ?
C30 H30 . 0.9500 ?
C31 H31 . 0.9500 ?
C32 H321 . 0.9800 ?
C32 H322 . 0.9800 ?
C32 H323 . 0.9800 ?
O8 H81O . 0.75(5) ?
O8 H82O . 0.75(5) ?
O7 C33 . 1.346(8) ?
O7 H7O . 0.923(8) ?
C33 H331 . 0.9800 ?
C33 H332 . 0.9800 ?
C33 H333 . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1N N3 . 0.83(3) 2.37(3) 2.986(2) 131(2)
N1 H1N N3 3_565 0.83(3) 2.38(3) 3.060(2) 139(2)
N2 H2N O5 3_665 0.84(3) 2.14(3) 2.847(2) 142(3)
N2 H2N O6 3_665 0.84(3) 2.21(3) 2.822(2) 130(2)
N4 H4N O1 3_565 0.90(3) 2.02(3) 2.919(2) 174(3)
N5 H5N N7 . 0.86(3) 2.21(3) 2.910(2) 138(2)
N5 H5N N7 3_655 0.86(3) 2.47(3) 3.098(2) 130(2)
N6 H6N O2 4_666 0.92(3) 2.53(3) 3.036(2) 115(2)
N6 H6N O3 4_666 0.92(3) 1.79(3) 2.667(2) 158(2)
N8 H8N O4 3_655 0.85(3) 2.21(3) 3.034(3) 164(3)
O7 H7O O8 . 0.923(8) 1.70(5) 2.480(8) 140(7)
O7 H7O O8 2_655 0.923(8) 2.50(10) 2.995(9) 114(8)
O8 H82O O6 . 0.75(5) 2.00(6) 2.735(5) 166(11)
O8 H81O O6 2_655 0.75(5) 2.02(6) 2.721(5) 158(12)
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
N1 C1 C2 C3 . . . . -176.8(2) ?
C5 C1 C2 C3 . . . . 3.5(3) ?
C1 C2 C3 N2 . . . . -1.9(3) ?
C2 C3 N2 C4 . . . . -0.8(3) ?
C3 N2 C4 C5 . . . . 1.7(3) ?
N2 C4 C5 C1 . . . . 0.1(3) ?
N2 C4 C5 S1 . . . . 176.95(16) ?
N1 C1 C5 C4 . . . . 177.7(2) ?
C2 C1 C5 C4 . . . . -2.6(3) ?
N1 C1 C5 S1 . . . . 1.0(3) ?
C2 C1 C5 S1 . . . . -179.31(15) ?
C4 C5 S1 O2 . . . . 10.41(19) ?
C1 C5 S1 O2 . . . . -172.81(16) ?
C4 C5 S1 O1 . . . . -111.79(17) ?
C1 C5 S1 O1 . . . . 64.99(18) ?
C4 C5 S1 N3 . . . . 135.05(17) ?
C1 C5 S1 N3 . . . . -48.17(18) ?
O2 S1 N3 C6 . . . . 57.06(17) ?
O1 S1 N3 C6 . . . . -172.47(14) ?
C5 S1 N3 C6 . . . . -60.20(16) ?
S1 N3 C6 O3 . . . . -15.8(3) ?
S1 N3 C6 N4 . . . . 163.11(15) ?
O3 C6 N4 C7 . . . . 9.4(3) ?
N3 C6 N4 C7 . . . . -169.6(2) ?
C6 N4 C7 C8 . . . . -164.5(2) ?
C6 N4 C7 C9 . . . . 73.9(3) ?
C2 C1 N1 C10 . . . . 10.9(3) ?
C5 C1 N1 C10 . . . . -169.43(19) ?
C1 N1 C10 C11 . . . . -125.7(2) ?
C1 N1 C10 C15 . . . . 57.9(3) ?
C15 C10 C11 C12 . . . . -0.2(3) ?
N1 C10 C11 C12 . . . . -176.6(2) ?
C10 C11 C12 C13 . . . . -0.9(3) ?
C10 C11 C12 C16 . . . . 178.8(2) ?
C11 C12 C13 C14 . . . . 1.1(4) ?
C16 C12 C13 C14 . . . . -178.5(3) ?
C12 C13 C14 C15 . . . . -0.3(4) ?
C13 C14 C15 C10 . . . . -0.9(4) ?
C11 C10 C15 C14 . . . . 1.1(4) ?
N1 C10 C15 C14 . . . . 177.5(2) ?
N5 C17 C18 C19 . . . . 175.5(2) ?
C21 C17 C18 C19 . . . . -3.0(3) ?
C17 C18 C19 N6 . . . . 1.2(4) ?
C18 C19 N6 C20 . . . . 0.6(3) ?
C19 N6 C20 C21 . . . . -0.5(3) ?
N6 C20 C21 C17 . . . . -1.5(3) ?
N6 C20 C21 S2 . . . . 178.14(16) ?
N5 C17 C21 C20 . . . . -175.4(2) ?
C18 C17 C21 C20 . . . . 3.1(3) ?
N5 C17 C21 S2 . . . . 5.0(3) ?
C18 C17 C21 S2 . . . . -176.49(16) ?
C20 C21 S2 O5 . . . . 3.78(19) ?
C17 C21 S2 O5 . . . . -176.60(16) ?
C20 C21 S2 O4 . . . . -118.87(17) ?
C17 C21 S2 O4 . . . . 60.75(18) ?
C20 C21 S2 N7 . . . . 128.44(17) ?
C17 C21 S2 N7 . . . . -51.94(18) ?
O5 S2 N7 C22 . . . . 54.98(17) ?
O4 S2 N7 C22 . . . . -174.19(14) ?
C21 S2 N7 C22 . . . . -62.19(16) ?
S2 N7 C22 O6 . . . . -16.3(3) ?
S2 N7 C22 N8 . . . . 163.34(16) ?
O6 C22 N8 C23 . . . . -1.3(4) ?
N7 C22 N8 C23 . . . . 179.1(2) ?
C22 N8 C23 C25 . . . . -110.2(4) ?
C22 N8 C23 C24 . . . . 131.5(3) ?
C18 C17 N5 C26 . . . . 11.2(3) ?
C21 C17 N5 C26 . . . . -170.33(19) ?
C17 N5 C26 C27 . . . . -112.5(2) ?
C17 N5 C26 C31 . . . . 71.3(3) ?
C31 C26 C27 C28 . . . . -0.4(3) ?
N5 C26 C27 C28 . . . . -176.50(18) ?
C26 C27 C28 C29 . . . . -0.2(3) ?
C26 C27 C28 C32 . . . . -179.9(2) ?
C27 C28 C29 C30 . . . . 1.0(3) ?
C32 C28 C29 C30 . . . . -179.3(2) ?
C28 C29 C30 C31 . . . . -1.1(4) ?
C29 C30 C31 C26 . . . . 0.5(3) ?
C27 C26 C31 C30 . . . . 0.2(3) ?
N5 C26 C31 C30 . . . . 176.38(19) ?
