#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/16/2221686.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_2221686
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 T--N): a low temperature redetermination
;
_journal_coeditor_code           HB2935
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o972
_journal_page_last               o973
_journal_paper_doi               10.1107/S1600536809012069
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H20 N4 O3 S'
_chemical_formula_moiety         'C16 H20 N4 O3 S'
_chemical_formula_sum            'C16 H20 N4 O3 S'
_chemical_formula_weight         348.42
_chemical_name_common            torasemide
_chemical_name_systematic
;
4-(3-Methylanilino)-N-[N-(1-methylethyl)carbamoyl]pyridinium-3-
sulfonamidate
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 94.2730(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.33780(10)
_cell_length_b                   18.90550(10)
_cell_length_c                   16.49580(10)
_cell_measurement_reflns_used    43504
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.21
_cell_measurement_theta_min      4.55
_cell_volume                     3525.99(4)
_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)'
_computing_publication_material
;SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999),
GAUSSIAN03 (Frisch et al.,2004) and
PARST (Nardelli, 1995)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.1241
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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     1.5418
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0116
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            53231
_diffrn_reflns_theta_full        72.64
_diffrn_reflns_theta_max         72.64
_diffrn_reflns_theta_min         4.56
_exptl_absorpt_coefficient_mu    1.821
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSPACK; Oxford Diffraction, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.356
_refine_ls_extinction_coef       0.0029(2)
_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   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     458
_refine_ls_number_reflns         6941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0429
_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)+(0.0678P)²+1.9103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1172
_reflns_number_gt                6840
_reflns_number_total             6941
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2935.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221686
_cod_database_fobs_code          2221686
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
C C1 0.06628(14) 0.35277(8) 0.09441(9) 0.0240(3) Uani d . 1 . .
C C2 0.05152(15) 0.28496(9) 0.12963(10) 0.0292(3) Uani d . 1 . .
H H2 -0.0181 0.2749 0.1562 0.035 Uiso calc R 1 . .
C C3 0.13599(15) 0.23451(9) 0.12564(11) 0.0308(4) Uani d . 1 . .
H H3 0.1238 0.1893 0.1487 0.037 Uiso calc R 1 . .
N N2 0.23689(12) 0.24714(7) 0.08976(9) 0.0281(3) Uani d . 1 . .
H H2N 0.2975(19) 0.2144(11) 0.0880(13) 0.034 Uiso d . 1 . .
C C4 0.25680(14) 0.31069(8) 0.05726(9) 0.0253(3) Uani d . 1 . .
H H4 0.3287 0.3186 0.0326 0.030 Uiso calc R 1 . .
C C5 0.17588(13) 0.36451(8) 0.05876(9) 0.0232(3) Uani d . 1 . .
S S1 0.20832(3) 0.446859(19) 0.01391(2) 0.02230(12) Uani d . 1 . .
O O1 0.19638(10) 0.49999(6) 0.07600(7) 0.0259(2) Uani d . 1 . .
O O2 0.32755(10) 0.44000(6) -0.01170(7) 0.0259(2) Uani d . 1 . .
N N3 0.10577(12) 0.45781(7) -0.05325(8) 0.0242(3) Uani d . 1 . .
C C6 0.09635(14) 0.41075(8) -0.11840(9) 0.0253(3) Uani d . 1 . .
O O3 0.17766(10) 0.37454(6) -0.14317(7) 0.0285(3) Uani d . 1 . .
N N4 -0.01530(13) 0.40839(8) -0.15352(9) 0.0319(3) Uani d . 1 . .
H H4N -0.069(2) 0.4363(12) -0.1341(14) 0.038 Uiso d . 1 . .
C C7 -0.04833(16) 0.36875(10) -0.22750(10) 0.0330(4) Uani d . 1 . .
H H7 0.0095 0.3292 -0.2316 0.040 Uiso calc R 1 . .
C C8 -0.1707(2) 0.33682(15) -0.22238(16) 0.0605(7) Uani d . 1 . .
H H81 -0.1694 0.3039 -0.1764 0.091 Uiso calc R 1 . .
H H82 -0.1936 0.3113 -0.2728 0.091 Uiso calc R 1 . .
H H83 -0.2279 0.3746 -0.2146 0.091 Uiso calc R 1 . .
C C9 -0.0425(2) 0.41555(12) -0.30182(12) 0.0474(5) Uani d . 1 . .
H H91 0.0377 0.4345 -0.3035 0.071 Uiso calc R 1 . .
H H92 -0.0987 0.4547 -0.2989 0.071 Uiso calc R 1 . .
H H93 -0.0627 0.3877 -0.3510 0.071 Uiso calc R 1 . .
N N1 -0.01871(12) 0.40159(7) 0.09416(8) 0.0252(3) Uani d . 1 . .
H H1N -0.0117(18) 0.4407(12) 0.0675(13) 0.030 Uiso d . 1 . .
C C10 -0.11809(14) 0.39528(8) 0.14235(10) 0.0247(3) Uani d . 1 . .
C C11 -0.22992(14) 0.38155(8) 0.10547(10) 0.0279(3) Uani d . 1 . .
H H11 -0.2402 0.3758 0.0482 0.033 Uiso calc R 1 . .
C C12 -0.32729(15) 0.37622(9) 0.15230(11) 0.0306(4) Uani d . 1 . .
C C13 -0.30887(15) 0.38601(9) 0.23606(11) 0.0327(4) Uani d . 1 . .
H H13 -0.3740 0.3823 0.2689 0.039 Uiso calc R 1 . .
C C14 -0.19782(16) 0.40100(10) 0.27239(11) 0.0338(4) Uani d . 1 . .
H H14 -0.1876 0.4084 0.3294 0.041 Uiso calc R 1 . .
C C15 -0.10120(15) 0.40520(9) 0.22556(10) 0.0300(3) Uani d . 1 . .
H H15 -0.0245 0.4148 0.2503 0.036 Uiso calc R 1 . .
C C16 -0.44868(16) 0.36000(11) 0.11375(14) 0.0426(5) Uani d . 1 . .
H H161 -0.4641 0.3092 0.1178 0.064 Uiso calc R 1 . .
H H162 -0.4532 0.3739 0.0564 0.064 Uiso calc R 1 . .
H H163 -0.5079 0.3863 0.1419 0.064 Uiso calc R 1 . .
C C17 0.53049(14) 0.00721(8) 0.20469(10) 0.0255(3) Uani d . 1 . .
C C18 0.57906(15) 0.00421(9) 0.28673(10) 0.0287(3) Uani d . 1 . .
H H18 0.6541 -0.0171 0.2990 0.034 Uiso calc R 1 . .
C C19 0.51868(16) 0.03167(9) 0.34779(10) 0.0303(3) Uani d . 1 . .
H H19 0.5517 0.0286 0.4023 0.036 Uiso calc R 1 . .
N N6 0.41244(13) 0.06327(8) 0.33205(9) 0.0295(3) Uani d . 1 . .
H H6N 0.3709(19) 0.0776(12) 0.3695(14) 0.035 Uiso d . 1 . .
C C20 0.36491(15) 0.07020(9) 0.25530(10) 0.0267(3) Uani d . 1 . .
H H20 0.2912 0.0938 0.2455 0.032 Uiso calc R 1 . .
C C21 0.42078(14) 0.04394(8) 0.19141(10) 0.0246(3) Uani d . 1 . .
S S2 0.34526(3) 0.048572(19) 0.09286(2) 0.02303(12) Uani d . 1 . .
O O4 0.24685(10) 0.09590(6) 0.10138(7) 0.0273(2) Uani d . 1 . .
O O5 0.31276(10) -0.02365(6) 0.07219(7) 0.0267(2) Uani d . 1 . .
N N7 0.43996(12) 0.07155(7) 0.03378(8) 0.0241(3) Uani d . 1 . .
C C22 0.48491(14) 0.13952(8) 0.03857(9) 0.0247(3) Uani d . 1 . .
O O6 0.44602(10) 0.18959(6) 0.07821(7) 0.0297(3) Uani d . 1 . .
N N8 0.57991(14) 0.14797(8) -0.00463(10) 0.0335(3) Uani d . 1 . .
H H8N 0.611(2) 0.1105(12) -0.0284(14) 0.040 Uiso d . 1 . .
C C23 0.64106(16) 0.21554(9) -0.00994(12) 0.0337(4) Uani d . 1 . .
H H23 0.6350 0.2413 0.0425 0.040 Uiso calc R 1 . .
C C24 0.5836(2) 0.26095(11) -0.07816(14) 0.0468(5) Uani d . 1 . .
H H241 0.5935 0.2382 -0.1306 0.070 Uiso calc R 1 . .
H H242 0.6211 0.3077 -0.0771 0.070 Uiso calc R 1 . .
H H243 0.4991 0.2662 -0.0707 0.070 Uiso calc R 1 . .
C C25 0.77101(18) 0.20277(11) -0.02102(15) 0.0462(5) Uani d . 1 . .
H H251 0.8055 0.1739 0.0241 0.069 Uiso calc R 1 . .
H H252 0.8125 0.2482 -0.0218 0.069 Uiso calc R 1 . .
H H253 0.7790 0.1779 -0.0725 0.069 Uiso calc R 1 . .
N N5 0.58380(12) -0.02241(8) 0.14337(8) 0.0278(3) Uani d . 1 . .
H H5N 0.5523(18) -0.0126(11) 0.0923(13) 0.033 Uiso d . 1 . .
C C26 0.67680(15) -0.07370(10) 0.15013(10) 0.0303(4) Uani d . 1 . .
C C27 0.77484(16) -0.06222(12) 0.10718(11) 0.0383(4) Uani d . 1 . .
H H27 0.7847 -0.0182 0.0808 0.046 Uiso calc R 1 . .
C C28 0.86000(18) -0.11553(17) 0.10247(13) 0.0596(7) Uani d . 1 . .
C C29 0.8433(3) -0.17915(16) 0.14258(17) 0.0703(9) Uani d . 1 . .
H H29 0.9001 -0.2158 0.1398 0.084 Uiso calc R 1 . .
C C30 0.7461(3) -0.18997(14) 0.18613(17) 0.0644(7) Uani d . 1 . .
H H30 0.7368 -0.2336 0.2135 0.077 Uiso calc R 1 . .
C C31 0.66150(19) -0.13720(11) 0.19027(13) 0.0449(5) Uani d . 1 . .
H H31 0.5941 -0.1445 0.2202 0.054 Uiso calc R 1 . .
C C32 0.9641(2) -0.1025(2) 0.05306(16) 0.0944(14) Uani d . 1 . .
H H321 1.0160 -0.1440 0.0560 0.142 Uiso calc R 1 . .
H H322 1.0082 -0.0611 0.0746 0.142 Uiso calc R 1 . .
H H323 0.9361 -0.0938 -0.0037 0.142 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 0.0181 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 . . 121.19(14) ?
N1 C1 C5 . . 122.72(14) ?
C2 C1 C5 . . 116.09(14) ?
C3 C2 C1 . . 120.58(15) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
N2 C3 C2 . . 121.47(15) ?
N2 C3 H3 . . 119.3 ?
C2 C3 H3 . . 119.3 ?
C4 N2 C3 . . 120.51(14) ?
C4 N2 H2N . . 116.0(13) ?
C3 N2 H2N . . 123.4(13) ?
N2 C4 C5 . . 121.63(15) ?
N2 C4 H4 . . 119.2 ?
C5 C4 H4 . . 119.2 ?
C4 C5 C1 . . 119.66(14) ?
C4 C5 S1 . . 118.93(12) ?
C1 C5 S1 . . 121.39(11) ?
O1 S1 O2 . . 113.94(7) ?
O1 S1 N3 . . 107.85(7) ?
O2 S1 N3 . . 117.80(7) ?
O1 S1 C5 . . 106.29(7) ?
O2 S1 C5 . . 105.64(7) ?
N3 S1 C5 . . 104.25(7) ?
C6 N3 S1 . . 118.27(11) ?
O3 C6 N4 . . 122.33(15) ?
O3 C6 N3 . . 126.15(15) ?
N4 C6 N3 . . 111.52(14) ?
C6 N4 C7 . . 123.33(14) ?
C6 N4 H4N . . 118.5(15) ?
C7 N4 H4N . . 117.8(15) ?
N4 C7 C9 . . 110.66(16) ?
N4 C7 C8 . . 109.64(15) ?
C9 C7 C8 . . 111.79(19) ?
N4 C7 H7 . . 108.2 ?
C9 C7 H7 . . 108.2 ?
C8 C7 H7 . . 108.2 ?
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 . . 122.61(13) ?
C1 N1 H1N . . 119.9(14) ?
C10 N1 H1N . . 117.3(14) ?
C15 C10 C11 . . 120.92(15) ?
C15 C10 N1 . . 118.87(14) ?
C11 C10 N1 . . 120.19(14) ?
C10 C11 C12 . . 120.28(16) ?
C10 C11 H11 . . 119.9 ?
C12 C11 H11 . . 119.9 ?
C13 C12 C11 . . 118.17(16) ?
C13 C12 C16 . . 120.72(16) ?
C11 C12 C16 . . 121.11(17) ?
C14 C13 C12 . . 121.40(15) ?
C14 C13 H13 . . 119.3 ?
C12 C13 H13 . . 119.3 ?
C13 C14 C15 . . 120.07(16) ?
C13 C14 H14 . . 120.0 ?
C15 C14 H14 . . 120.0 ?
C10 C15 C14 . . 119.15(16) ?
C10 C15 H15 . . 120.4 ?
C14 C15 H15 . . 120.4 ?
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 . . 122.48(15) ?
N5 C17 C21 . . 121.66(14) ?
C18 C17 C21 . . 115.86(14) ?
C19 C18 C17 . . 120.50(15) ?
C19 C18 H18 . . 119.7 ?
C17 C18 H18 . . 119.7 ?
N6 C19 C18 . . 121.06(15) ?
N6 C19 H19 . . 119.5 ?
C18 C19 H19 . . 119.5 ?
C20 N6 C19 . . 120.83(15) ?
C20 N6 H6N . . 116.7(15) ?
C19 N6 H6N . . 122.4(15) ?
N6 C20 C21 . . 121.05(15) ?
N6 C20 H20 . . 119.5 ?
C21 C20 H20 . . 119.5 ?
C20 C21 C17 . . 120.57(15) ?
C20 C21 S2 . . 117.91(12) ?
C17 C21 S2 . . 121.19(12) ?
O4 S2 O5 . . 114.95(7) ?
O4 S2 N7 . . 117.35(7) ?
O5 S2 N7 . . 106.83(7) ?
O4 S2 C21 . . 105.28(7) ?
O5 S2 C21 . . 105.36(7) ?
N7 S2 C21 . . 106.05(7) ?
C22 N7 S2 . . 119.33(11) ?
O6 C22 N8 . . 121.01(15) ?
O6 C22 N7 . . 126.24(15) ?
N8 C22 N7 . . 112.75(14) ?
C22 N8 C23 . . 122.60(14) ?
C22 N8 H8N . . 119.8(14) ?
C23 N8 H8N . . 117.4(14) ?
N8 C23 C25 . . 109.75(15) ?
N8 C23 C24 . . 111.02(16) ?
C25 C23 C24 . . 111.51(17) ?
N8 C23 H23 . . 108.1 ?
C25 C23 H23 . . 108.1 ?
C24 C23 H23 . . 108.1 ?
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 . . 126.59(14) ?
C17 N5 H5N . . 116.5(13) ?
C26 N5 H5N . . 116.5(13) ?
C27 C26 C31 . . 121.01(17) ?
C27 C26 N5 . . 118.10(16) ?
C31 C26 N5 . . 120.38(17) ?
C26 C27 C28 . . 120.0(2) ?
C26 C27 H27 . . 120.0 ?
C28 C27 H27 . . 120.0 ?
C29 C28 C27 . . 118.4(2) ?
C29 C28 C32 . . 122.7(3) ?
C27 C28 C32 . . 118.9(3) ?
C30 C29 C28 . . 121.3(2) ?
C30 C29 H29 . . 119.3 ?
C28 C29 H29 . . 119.3 ?
C29 C30 C31 . . 120.1(3) ?
C29 C30 H30 . . 119.9 ?
C31 C30 H30 . . 119.9 ?
C26 C31 C30 . . 119.1(2) ?
C26 C31 H31 . . 120.4 ?
C30 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 ?
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 . 1.334(2) ?
C1 C2 . 1.422(2) ?
C1 C5 . 1.431(2) ?
C2 C3 . 1.357(2) ?
C2 H2 . 0.9500 ?
C3 N2 . 1.348(2) ?
C3 H3 . 0.9500 ?
N2 C4 . 1.342(2) ?
N2 H2N . 0.93(2) ?
C4 C5 . 1.372(2) ?
C4 H4 . 0.9500 ?
C5 S1 . 1.7740(16) ?
S1 O1 . 1.4481(11) ?
S1 O2 . 1.4518(11) ?
S1 N3 . 1.5589(13) ?
N3 C6 . 1.393(2) ?
C6 O3 . 1.2416(19) ?
C6 N4 . 1.353(2) ?
N4 C7 . 1.457(2) ?
N4 H4N . 0.89(2) ?
C7 C9 . 1.517(3) ?
C7 C8 . 1.521(3) ?
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 . 1.4316(19) ?
N1 H1N . 0.87(2) ?
C10 C15 . 1.384(2) ?
C10 C11 . 1.389(2) ?
C11 C12 . 1.397(2) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.394(3) ?
C12 C16 . 1.504(2) ?
C13 C14 . 1.383(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.389(2) ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
C16 H161 . 0.9800 ?
C16 H162 . 0.9800 ?
C16 H163 . 0.9800 ?
C17 N5 . 1.339(2) ?
C17 C18 . 1.424(2) ?
C17 C21 . 1.427(2) ?
C18 C19 . 1.362(2) ?
C18 H18 . 0.9500 ?
C19 N6 . 1.352(2) ?
C19 H19 . 0.9500 ?
N6 C20 . 1.345(2) ?
N6 H6N . 0.85(2) ?
C20 C21 . 1.363(2) ?
C20 H20 . 0.9500 ?
C21 S2 . 1.7823(16) ?
S2 O4 . 1.4452(11) ?
S2 O5 . 1.4483(12) ?
S2 N7 . 1.5643(13) ?
N7 C22 . 1.382(2) ?
C22 O6 . 1.2495(19) ?
C22 N8 . 1.345(2) ?
N8 C23 . 1.459(2) ?
N8 H8N . 0.90(2) ?
C23 C25 . 1.517(2) ?
C23 C24 . 1.523(3) ?
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 . 1.431(2) ?
N5 H5N . 0.91(2) ?
C26 C27 . 1.379(3) ?
C26 C31 . 1.388(3) ?
C27 C28 . 1.402(3) ?
C27 H27 . 0.9500 ?
C28 C29 . 1.393(4) ?
C28 C32 . 1.504(4) ?
C29 C30 . 1.375(4) ?
C29 H29 . 0.9500 ?
C30 C31 . 1.389(3) ?
C30 H30 . 0.9500 ?
C31 H31 . 0.9500 ?
C32 H321 . 0.9800 ?
C32 H322 . 0.9800 ?
C32 H323 . 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 . 0.87(2) 2.50(2) 3.0897(18) 126.1(17)
N5 H5N N7 . 0.91(2) 2.21(2) 2.9399(19) 136.4(18)
N4 H4N O1 3_565 0.89(2) 2.16(2) 3.0400(18) 175(2)
N8 H8N O5 3_655 0.90(2) 2.01(2) 2.9067(18) 175(2)
N1 H1N N3 3_565 0.87(2) 2.20(2) 2.8977(19) 137.4(18)
N5 H5N N7 3_655 0.91(2) 2.37(2) 3.0591(19) 132.9(17)
N2 H2N O4 . 0.93(2) 2.33(2) 2.8674(18) 116.8(16)
N6 H6N O2 4_566 0.85(2) 2.08(2) 2.8184(18) 145(2)
N2 H2N O6 . 0.93(2) 1.77(2) 2.6286(17) 153.4(19)
N6 H6N O3 4_566 0.85(2) 2.37(2) 2.9660(19) 128.2(18)
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 . . . . 176.46(16) ?
C5 C1 C2 C3 . . . . -2.6(2) ?
C1 C2 C3 N2 . . . . 1.2(3) ?
C2 C3 N2 C4 . . . . 0.4(3) ?
C3 N2 C4 C5 . . . . -0.4(2) ?
N2 C4 C5 C1 . . . . -1.2(2) ?
N2 C4 C5 S1 . . . . -179.61(12) ?
N1 C1 C5 C4 . . . . -176.47(15) ?
C2 C1 C5 C4 . . . . 2.6(2) ?
N1 C1 C5 S1 . . . . 1.9(2) ?
C2 C1 C5 S1 . . . . -178.98(12) ?
C4 C5 S1 O1 . . . . -125.64(13) ?
C1 C5 S1 O1 . . . . 55.93(14) ?
C4 C5 S1 O2 . . . . -4.25(15) ?
C1 C5 S1 O2 . . . . 177.32(12) ?
C4 C5 S1 N3 . . . . 120.55(13) ?
C1 C5 S1 N3 . . . . -57.88(14) ?
O1 S1 N3 C6 . . . . -177.62(11) ?
O2 S1 N3 C6 . . . . 51.70(14) ?
C5 S1 N3 C6 . . . . -64.93(13) ?
S1 N3 C6 O3 . . . . -23.6(2) ?
S1 N3 C6 N4 . . . . 156.37(12) ?
O3 C6 N4 C7 . . . . -5.9(3) ?
N3 C6 N4 C7 . . . . 174.09(15) ?
C6 N4 C7 C9 . . . . -92.7(2) ?
C6 N4 C7 C8 . . . . 143.5(2) ?
C2 C1 N1 C10 . . . . 12.9(2) ?
C5 C1 N1 C10 . . . . -168.03(15) ?
C1 N1 C10 C15 . . . . 73.0(2) ?
C1 N1 C10 C11 . . . . -108.95(18) ?
C15 C10 C11 C12 . . . . -1.2(2) ?
N1 C10 C11 C12 . . . . -179.23(14) ?
C10 C11 C12 C13 . . . . 0.9(2) ?
C10 C11 C12 C16 . . . . -178.81(16) ?
C11 C12 C13 C14 . . . . 0.4(3) ?
C16 C12 C13 C14 . . . . -179.96(17) ?
C12 C13 C14 C15 . . . . -1.3(3) ?
C11 C10 C15 C14 . . . . 0.2(2) ?
N1 C10 C15 C14 . . . . 178.32(15) ?
C13 C14 C15 C10 . . . . 1.0(3) ?
N5 C17 C18 C19 . . . . -176.36(16) ?
C21 C17 C18 C19 . . . . 3.7(2) ?
C17 C18 C19 N6 . . . . -1.0(3) ?
C18 C19 N6 C20 . . . . -1.9(3) ?
C19 N6 C20 C21 . . . . 1.8(2) ?
N6 C20 C21 C17 . . . . 1.1(2) ?
N6 C20 C21 S2 . . . . 174.53(12) ?
N5 C17 C21 C20 . . . . 176.28(16) ?
C18 C17 C21 C20 . . . . -3.7(2) ?
N5 C17 C21 S2 . . . . 3.1(2) ?
C18 C17 C21 S2 . . . . -176.91(12) ?
C20 C21 S2 O4 . . . . 12.97(15) ?
C17 C21 S2 O4 . . . . -173.67(13) ?
C20 C21 S2 O5 . . . . -108.94(13) ?
C17 C21 S2 O5 . . . . 64.42(14) ?
C20 C21 S2 N7 . . . . 138.01(13) ?
C17 C21 S2 N7 . . . . -48.63(15) ?
O4 S2 N7 C22 . . . . 47.61(14) ?
O5 S2 N7 C22 . . . . 178.36(11) ?
C21 S2 N7 C22 . . . . -69.62(13) ?
S2 N7 C22 O6 . . . . -10.9(2) ?
S2 N7 C22 N8 . . . . 168.51(12) ?
O6 C22 N8 C23 . . . . -1.7(3) ?
N7 C22 N8 C23 . . . . 178.84(15) ?
C22 N8 C23 C25 . . . . 149.93(18) ?
C22 N8 C23 C24 . . . . -86.3(2) ?
C18 C17 N5 C26 . . . . 15.8(3) ?
C21 C17 N5 C26 . . . . -164.23(16) ?
C17 N5 C26 C27 . . . . -131.35(18) ?
C17 N5 C26 C31 . . . . 56.8(3) ?
C31 C26 C27 C28 . . . . 1.0(3) ?
N5 C26 C27 C28 . . . . -170.78(16) ?
C26 C27 C28 C29 . . . . -0.6(3) ?
C26 C27 C28 C32 . . . . 178.09(19) ?
C27 C28 C29 C30 . . . . -0.2(3) ?
C32 C28 C29 C30 . . . . -178.8(2) ?
C28 C29 C30 C31 . . . . 0.6(4) ?
C27 C26 C31 C30 . . . . -0.6(3) ?
N5 C26 C31 C30 . . . . 171.00(19) ?
C29 C30 C31 C26 . . . . -0.2(3) ?
