#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/97/2229703.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_2229703
loop_
_publ_author_name
'Huang, Ting-Ting'
'Meng, Na-Na'
'Qing, Xiao-Yu'
'Yu, Luo-Ting'
_publ_section_title
;
 4-{[4-(3,5-Dimethoxybenzamido)phenyl]sulfanyl}-N-methylpyridine-2-carboxamide
;
_journal_coeditor_code           IM2258
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o856
_journal_paper_doi               10.1107/S1600536811006490
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C22 H21 N3 O4 S'
_chemical_formula_moiety         'C22 H21 N3 O4 S'
_chemical_formula_sum            'C22 H21 N3 O4 S'
_chemical_formula_weight         423.49
_chemical_name_systematic
;
4-{[4-(3,5-Dimethoxybenzamido)phenyl]sulfanyl}-N-methylpyridine-
2-carboxamide
;
_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           SHELXL-97
_cell_angle_alpha                102.723(4)
_cell_angle_beta                 105.949(4)
_cell_angle_gamma                90.975(4)
_cell_formula_units_Z            4
_cell_length_a                   11.1165(5)
_cell_length_b                   13.5678(6)
_cell_length_c                   15.3183(6)
_cell_measurement_reflns_used    5046
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2428
_cell_measurement_theta_min      2.8964
_cell_volume                     2159.51(17)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0960
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18448
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.98909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2010)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         8806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0435
_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)+(0.0126P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0652
_reflns_number_gt                4117
_reflns_number_total             8806
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2258.cif
_cod_data_source_block           I
_cod_original_cell_volume        2159.51(16)
_cod_database_code               2229703
_cod_database_fobs_code          2229703
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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
S S1 0.65660(6) 0.37812(4) 1.12524(4) 0.05655(19) Uani d . 1 . .
O O1 0.39178(13) 0.32537(11) 0.17737(9) 0.0536(4) Uani d . 1 . .
O O2 0.33947(17) -0.01920(13) 0.01326(11) 0.0862(6) Uani d . 1 . .
O O3 0.64974(15) 0.00594(12) 0.34157(10) 0.0708(5) Uani d . 1 . .
O O4 0.64438(14) -0.26093(10) 0.57675(10) 0.0568(4) Uani d . 1 . .
N N1 0.56894(16) 0.13586(12) 0.42239(12) 0.0541(5) Uani d . 1 . .
H H1 0.5175 0.1823 0.4170 0.065 Uiso calc R 1 . .
N N2 0.89197(18) -0.23172(14) 0.78726(14) 0.0582(5) Uani d . 1 . .
N N3 0.74299(16) -0.37746(14) 0.64935(12) 0.0553(5) Uani d . 1 . .
H H3 0.8025 -0.3878 0.6951 0.066 Uiso calc R 1 . .
C C1 0.48731(19) 0.20452(16) 0.25279(15) 0.0453(6) Uani d . 1 . .
H H1A 0.5205 0.2565 0.3056 0.054 Uiso calc R 1 . .
C C2 0.4130(2) 0.22594(17) 0.17137(16) 0.0409(6) Uani d . 1 . .
C C3 0.3640(2) 0.14940(17) 0.09286(15) 0.0513(6) Uani d . 1 . .
H H3A 0.3123 0.1638 0.0389 0.062 Uiso calc R 1 . .
C C4 0.3926(2) 0.05029(18) 0.09486(17) 0.0553(7) Uani d . 1 . .
C C5 0.4657(2) 0.02726(17) 0.17531(17) 0.0555(7) Uani d . 1 . .
H H5 0.4841 -0.0392 0.1764 0.067 Uiso calc R 1 . .
C C6 0.5116(2) 0.10566(18) 0.25486(16) 0.0460(6) Uani d . 1 . .
C C7 0.3120(2) 0.35033(16) 0.09594(15) 0.0696(7) Uani d . 1 . .
H H7B 0.3508 0.3355 0.0462 0.104 Uiso calc R 1 . .
H H7C 0.2990 0.4212 0.1096 0.104 Uiso calc R 1 . .
H H7A 0.2327 0.3110 0.0773 0.104 Uiso calc R 1 . .
C C8 0.3678(2) -0.12126(17) 0.00739(16) 0.0935(10) Uani d . 1 . .
H H8C 0.4572 -0.1244 0.0242 0.140 Uiso calc R 1 . .
H H8B 0.3313 -0.1602 -0.0553 0.140 Uiso calc R 1 . .
H H8A 0.3342 -0.1485 0.0493 0.140 Uiso calc R 1 . .
C C9 0.5843(2) 0.07740(18) 0.34252(16) 0.0508(6) Uani d . 1 . .
C C10 0.6310(2) 0.12627(15) 0.51350(16) 0.0461(6) Uani d . 1 . .
C C11 0.7543(2) 0.10139(15) 0.53712(16) 0.0557(7) Uani d . 1 . .
H H11 0.7976 0.0900 0.4923 0.067 Uiso calc R 1 . .
C C12 0.8126(2) 0.09347(15) 0.62633(16) 0.0520(6) Uani d . 1 . .
H H12 0.8951 0.0761 0.6413 0.062 Uiso calc R 1 . .
C C13 0.7502(2) 0.11111(15) 0.69480(15) 0.0465(6) Uani d . 1 . .
C C14 0.6284(2) 0.13777(15) 0.67162(16) 0.0544(6) Uani d . 1 . .
H H14 0.5857 0.1508 0.7168 0.065 Uiso calc R 1 . .
C C15 0.5693(2) 0.14532(15) 0.58157(16) 0.0551(6) Uani d . 1 . .
H H15 0.4871 0.1634 0.5667 0.066 Uiso calc R 1 . .
C C16 0.8519(2) -0.02610(16) 0.79660(15) 0.0460(6) Uani d . 1 . .
C C17 0.9419(2) -0.05579(18) 0.86601(15) 0.0579(7) Uani d . 1 . .
H H17 0.9908 -0.0079 0.9174 0.069 Uiso calc R 1 . .
C C18 0.9577(2) -0.1577(2) 0.85779(17) 0.0688(8) Uani d . 1 . .
H H18 1.0190 -0.1761 0.9051 0.083 Uiso calc R 1 . .
C C19 0.8052(2) -0.20169(17) 0.72111(15) 0.0430(6) Uani d . 1 . .
C C20 0.78341(19) -0.10110(16) 0.72188(14) 0.0431(6) Uani d . 1 . .
H H20 0.7235 -0.0845 0.6728 0.052 Uiso calc R 1 . .
C C21 0.7239(2) -0.28288(18) 0.64210(16) 0.0450(6) Uani d . 1 . .
C C22 0.6663(2) -0.46444(16) 0.58221(16) 0.0773(8) Uani d . 1 . .
H H22B 0.5870 -0.4711 0.5949 0.116 Uiso calc R 1 . .
H H22C 0.7088 -0.5248 0.5874 0.116 Uiso calc R 1 . .
H H22A 0.6526 -0.4546 0.5201 0.116 Uiso calc R 1 . .
S S2 0.83017(6) 0.10378(4) 0.80987(4) 0.06080(19) Uani d . 1 . .
O O5 1.15357(17) 0.53884(17) 0.58562(12) 0.0965(6) Uani d . 1 . .
O O6 1.08908(16) 0.18987(14) 0.57927(12) 0.0908(6) Uani d . 1 . .
O O7 0.84584(14) 0.49944(11) 0.78247(10) 0.0623(5) Uani d . 1 . .
O O8 0.83861(13) 0.74737(10) 1.12151(10) 0.0537(4) Uani d . 1 . .
N N4 0.93679(14) 0.37157(11) 0.84322(11) 0.0444(5) Uani d . 1 . .
H H4 0.9932 0.3291 0.8417 0.053 Uiso calc R 1 . .
N N5 0.62508(15) 0.71220(13) 1.24900(12) 0.0482(5) Uani d . 1 . .
N N6 0.74652(15) 0.86110(13) 1.20748(11) 0.0523(5) Uani d . 1 . .
H H6 0.6911 0.8696 1.2376 0.063 Uiso calc R 1 . .
C C23 1.03238(19) 0.48973(17) 0.68142(14) 0.0529(6) Uani d . 1 . .
H H23 1.0154 0.5559 0.7038 0.063 Uiso calc R 1 . .
C C24 1.1014(2) 0.4680(2) 0.61764(17) 0.0623(7) Uani d . 1 . .
C C25 1.1221(2) 0.3681(2) 0.58183(15) 0.0676(8) Uani d . 1 . .
H H25 1.1677 0.3542 0.5385 0.081 Uiso calc R 1 . .
C C26 1.0758(2) 0.2906(2) 0.61010(17) 0.0612(7) Uani d . 1 . .
C C27 1.00969(19) 0.31162(17) 0.67610(15) 0.0547(7) Uani d . 1 . .
H H27 0.9795 0.2591 0.6964 0.066 Uiso calc R 1 . .
C C28 0.98907(19) 0.40933(17) 0.71110(14) 0.0443(6) Uani d . 1 . .
C C29 1.1378(3) 0.6419(2) 0.61998(19) 0.1054(11) Uani d . 1 . .
H H29A 1.0500 0.6523 0.6043 0.158 Uiso calc R 1 . .
H H29B 1.1800 0.6835 0.5924 0.158 Uiso calc R 1 . .
H H29C 1.1728 0.6599 0.6866 0.158 Uiso calc R 1 . .
C C30 1.1599(3) 0.1633(2) 0.51522(19) 0.1318(13) Uani d . 1 . .
H H30A 1.1195 0.1831 0.4585 0.198 Uiso calc R 1 . .
H H30B 1.1658 0.0913 0.5019 0.198 Uiso calc R 1 . .
H H30C 1.2426 0.1973 0.5417 0.198 Uiso calc R 1 . .
C C31 0.9166(2) 0.43189(17) 0.78087(15) 0.0454(6) Uani d . 1 . .
C C32 0.8700(2) 0.37503(14) 0.91011(15) 0.0378(5) Uani d . 1 . .
C C33 0.93255(19) 0.36860(14) 0.99944(15) 0.0471(6) Uani d . 1 . .
H H33 1.0186 0.3627 1.0155 0.057 Uiso calc R 1 . .
C C34 0.8686(2) 0.37083(14) 1.06550(14) 0.0488(6) Uani d . 1 . .
H H34 0.9121 0.3669 1.1257 0.059 Uiso calc R 1 . .
C C35 0.7406(2) 0.37881(14) 1.04267(15) 0.0407(6) Uani d . 1 . .
C C36 0.67767(19) 0.38272(14) 0.95225(15) 0.0464(6) Uani d . 1 . .
H H36 0.5913 0.3874 0.9357 0.056 Uiso calc R 1 . .
C C37 0.7419(2) 0.37978(14) 0.88621(15) 0.0476(6) Uani d . 1 . .
H H37 0.6983 0.3810 0.8253 0.057 Uiso calc R 1 . .
C C38 0.64704(18) 0.50777(15) 1.17087(13) 0.0402(6) Uani d . 1 . .
C C39 0.57828(19) 0.53448(17) 1.23420(15) 0.0491(6) Uani d . 1 . .
H H39 0.5380 0.4849 1.2520 0.059 Uiso calc R 1 . .
C C40 0.57063(19) 0.63515(18) 1.27021(14) 0.0540(6) Uani d . 1 . .
H H40 0.5241 0.6514 1.3127 0.065 Uiso calc R 1 . .
C C41 0.69385(18) 0.68463(16) 1.18968(14) 0.0397(6) Uani d . 1 . .
C C42 0.70578(17) 0.58534(15) 1.14923(13) 0.0396(5) Uani d . 1 . .
H H42 0.7535 0.5708 1.1074 0.047 Uiso calc R 1 . .
C C43 0.76637(19) 0.76806(17) 1.16986(15) 0.0433(6) Uani d . 1 . .
C C44 0.8143(2) 0.94991(15) 1.20025(15) 0.0692(8) Uani d . 1 . .
H H44B 0.8810 0.9292 1.1734 0.104 Uiso calc R 1 . .
H H44C 0.8488 0.9933 1.2613 0.104 Uiso calc R 1 . .
H H44A 0.7579 0.9859 1.1612 0.104 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
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
O1 C2 C1 . . 115.0(2) ?
O1 C2 C3 . . 124.5(2) ?
O1 C7 H7B . . 109.5 ?
O1 C7 H7C . . 109.5 ?
O1 C7 H7A . . 109.5 ?
O2 C4 C3 . . 114.4(2) ?
O2 C4 C5 . . 124.6(2) ?
O2 C8 H8C . . 109.5 ?
O2 C8 H8B . . 109.5 ?
O2 C8 H8A . . 109.5 ?
O3 C9 N1 . . 123.0(2) ?
O3 C9 C6 . . 122.3(2) ?
O4 C21 N3 . . 123.5(2) ?
O4 C21 C19 . . 121.2(2) ?
N1 C9 C6 . . 114.6(2) ?
N2 C18 C17 . . 124.9(2) ?
N2 C18 H18 . . 117.5 ?
N2 C19 C20 . . 124.2(2) ?
N2 C19 C21 . . 117.5(2) ?
N3 C21 C19 . . 115.3(2) ?
N3 C22 H22B . . 109.5 ?
N3 C22 H22C . . 109.5 ?
N3 C22 H22A . . 109.5 ?
C1 C6 C5 . . 120.9(2) ?
C1 C6 C9 . . 121.8(2) ?
C2 O1 C7 . . 116.82(17) ?
C2 C1 H1A . . 120.2 ?
C2 C3 H3A . . 120.3 ?
C2 C3 C4 . . 119.4(2) ?
C3 C2 C1 . . 120.5(2) ?
C4 O2 C8 . . 118.42(19) ?
C4 C3 H3A . . 120.3 ?
C4 C5 H5 . . 120.7 ?
C4 C5 C6 . . 118.6(2) ?
C5 C4 C3 . . 121.0(2) ?
C5 C6 C9 . . 117.3(2) ?
C6 C1 H1A . . 120.2 ?
C6 C1 C2 . . 119.6(2) ?
C6 C5 H5 . . 120.7 ?
H7B C7 H7C . . 109.5 ?
H7B C7 H7A . . 109.5 ?
H7C C7 H7A . . 109.5 ?
H8C C8 H8B . . 109.5 ?
H8C C8 H8A . . 109.5 ?
H8B C8 H8A . . 109.5 ?
C9 N1 H1 . . 117.5 ?
C9 N1 C10 . . 125.04(19) ?
C10 N1 H1 . . 117.5 ?
C10 C11 H11 . . 119.9 ?
C10 C15 C14 . . 120.7(2) ?
C10 C15 H15 . . 119.7 ?
C11 C10 N1 . . 121.4(2) ?
C11 C12 H12 . . 119.5 ?
C11 C12 C13 . . 120.9(2) ?
C12 C11 C10 . . 120.2(2) ?
C12 C11 H11 . . 119.9 ?
C12 C13 S2 . . 119.56(18) ?
C13 C12 H12 . . 119.5 ?
C13 C14 H14 . . 119.8 ?
C13 C14 C15 . . 120.4(2) ?
C14 C13 C12 . . 118.7(2) ?
C14 C13 S2 . . 121.66(18) ?
C14 C15 H15 . . 119.7 ?
C15 C10 N1 . . 119.5(2) ?
C15 C10 C11 . . 119.0(2) ?
C15 C14 H14 . . 119.8 ?
C16 C17 H17 . . 120.6 ?
C16 C20 C19 . . 119.1(2) ?
C16 C20 H20 . . 120.5 ?
C16 S2 C13 . . 102.47(10) ?
C17 C16 S2 . . 118.17(19) ?
C17 C18 H18 . . 117.5 ?
C18 N2 C19 . . 115.4(2) ?
C18 C17 C16 . . 118.8(2) ?
C18 C17 H17 . . 120.6 ?
C19 C20 H20 . . 120.5 ?
C20 C16 C17 . . 117.5(2) ?
C20 C16 S2 . . 124.28(18) ?
C20 C19 C21 . . 118.4(2) ?
C21 N3 H3 . . 118.9 ?
C21 N3 C22 . . 122.1(2) ?
C22 N3 H3 . . 118.9 ?
H22B C22 H22C . . 109.5 ?
H22B C22 H22A . . 109.5 ?
H22C C22 H22A . . 109.5 ?
O5 C24 C23 . . 124.4(3) ?
O5 C24 C25 . . 115.1(2) ?
O5 C29 H29A . . 109.5 ?
O5 C29 H29B . . 109.5 ?
O5 C29 H29C . . 109.5 ?
O6 C26 C27 . . 114.7(2) ?
O6 C30 H30A . . 109.5 ?
O6 C30 H30B . . 109.5 ?
O6 C30 H30C . . 109.5 ?
O7 C31 N4 . . 122.79(19) ?
O7 C31 C28 . . 122.51(19) ?
O8 C43 N6 . . 124.05(19) ?
O8 C43 C41 . . 120.4(2) ?
N4 C31 C28 . . 114.70(19) ?
N5 C40 C39 . . 125.08(19) ?
N5 C40 H40 . . 117.5 ?
N5 C41 C42 . . 123.90(18) ?
N5 C41 C43 . . 117.27(19) ?
N6 C43 C41 . . 115.56(19) ?
N6 C44 H44B . . 109.5 ?
N6 C44 H44C . . 109.5 ?
N6 C44 H44A . . 109.5 ?
C23 C24 C25 . . 120.5(2) ?
C23 C28 C31 . . 118.6(2) ?
C24 O5 C29 . . 118.1(2) ?
C24 C23 H23 . . 121.0 ?
C24 C23 C28 . . 118.1(2) ?
C24 C25 H25 . . 119.9 ?
C25 C26 O6 . . 125.5(2) ?
C25 C26 C27 . . 119.8(2) ?
C26 O6 C30 . . 117.80(19) ?
C26 C25 C24 . . 120.3(2) ?
C26 C25 H25 . . 119.9 ?
C26 C27 H27 . . 120.0 ?
C27 C28 C23 . . 121.31(19) ?
C27 C28 C31 . . 120.11(19) ?
C28 C23 H23 . . 121.0 ?
C28 C27 C26 . . 120.0(2) ?
C28 C27 H27 . . 120.0 ?
H29A C29 H29B . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
H30A C30 H30B . . 109.5 ?
H30A C30 H30C . . 109.5 ?
H30B C30 H30C . . 109.5 ?
C31 N4 H4 . . 118.2 ?
C31 N4 C32 . . 123.61(17) ?
C32 N4 H4 . . 118.2 ?
C32 C33 H33 . . 119.7 ?
C32 C33 C34 . . 120.7(2) ?
C32 C37 C36 . . 120.4(2) ?
C32 C37 H37 . . 119.8 ?
C33 C32 N4 . . 119.8(2) ?
C33 C34 H34 . . 119.8 ?
C34 C33 H33 . . 119.7 ?
C34 C35 S1 . . 121.10(18) ?
C34 C35 C36 . . 118.69(19) ?
C35 C34 C33 . . 120.5(2) ?
C35 C34 H34 . . 119.8 ?
C35 C36 H36 . . 119.7 ?
C35 C36 C37 . . 120.6(2) ?
C36 C35 S1 . . 120.15(17) ?
C36 C37 H37 . . 119.8 ?
C37 C32 N4 . . 121.0(2) ?
C37 C32 C33 . . 119.08(19) ?
C37 C36 H36 . . 119.7 ?
C38 S1 C35 . . 103.42(9) ?
C38 C39 H39 . . 120.6 ?
C38 C42 C41 . . 119.88(17) ?
C38 C42 H42 . . 120.1 ?
C39 C38 S1 . . 118.50(15) ?
C39 C40 H40 . . 117.5 ?
C40 C39 C38 . . 118.88(18) ?
C40 C39 H39 . . 120.6 ?
C41 N5 C40 . . 115.00(18) ?
C41 C42 H42 . . 120.1 ?
C42 C38 S1 . . 124.27(15) ?
C42 C38 C39 . . 117.22(19) ?
C42 C41 C43 . . 118.77(18) ?
C43 N6 H6 . . 118.7 ?
C43 N6 C44 . . 122.66(17) ?
C44 N6 H6 . . 118.7 ?
H44B C44 H44C . . 109.5 ?
H44B C44 H44A . . 109.5 ?
H44C C44 H44A . . 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
S1 C35 . 1.7682(19) ?
S1 C38 . 1.761(2) ?
O1 C2 . 1.361(2) ?
O1 C7 . 1.430(2) ?
O2 C4 . 1.362(2) ?
O2 C8 . 1.414(2) ?
O3 C9 . 1.222(2) ?
O4 C21 . 1.235(2) ?
N1 H1 . 0.8600 ?
N1 C9 . 1.359(2) ?
N1 C10 . 1.412(2) ?
N2 C18 . 1.332(3) ?
N2 C19 . 1.335(2) ?
N3 H3 . 0.8600 ?
N3 C21 . 1.328(2) ?
N3 C22 . 1.458(2) ?
C1 H1A . 0.9300 ?
C1 C2 . 1.387(3) ?
C1 C6 . 1.378(2) ?
C2 C3 . 1.375(3) ?
C3 H3A . 0.9300 ?
C3 C4 . 1.392(3) ?
C4 C5 . 1.380(3) ?
C5 H5 . 0.9300 ?
C5 C6 . 1.395(3) ?
C6 C9 . 1.498(3) ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C7 H7A . 0.9600 ?
C8 H8C . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8A . 0.9600 ?
C10 C11 . 1.386(3) ?
C10 C15 . 1.380(2) ?
C11 H11 . 0.9300 ?
C11 C12 . 1.371(3) ?
C12 H12 . 0.9300 ?
C12 C13 . 1.391(2) ?
C13 C14 . 1.378(3) ?
C13 S2 . 1.768(2) ?
C14 H14 . 0.9300 ?
C14 C15 . 1.383(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.382(3) ?
C16 C20 . 1.381(3) ?
C16 S2 . 1.757(2) ?
C17 H17 . 0.9300 ?
C17 C18 . 1.380(3) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.388(2) ?
C19 C21 . 1.507(3) ?
C20 H20 . 0.9300 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
C22 H22A . 0.9600 ?
O5 C24 . 1.358(2) ?
O5 C29 . 1.413(3) ?
O6 C26 . 1.368(3) ?
O6 C30 . 1.411(2) ?
O7 C31 . 1.218(2) ?
O8 C43 . 1.231(2) ?
N4 H4 . 0.8600 ?
N4 C31 . 1.366(2) ?
N4 C32 . 1.415(2) ?
N5 C40 . 1.342(2) ?
N5 C41 . 1.339(2) ?
N6 H6 . 0.8600 ?
N6 C43 . 1.317(2) ?
N6 C44 . 1.451(2) ?
C23 H23 . 0.9300 ?
C23 C24 . 1.387(3) ?
C23 C28 . 1.396(2) ?
C24 C25 . 1.394(3) ?
C25 H25 . 0.9300 ?
C25 C26 . 1.365(3) ?
C26 C27 . 1.390(3) ?
C27 H27 . 0.9300 ?
C27 C28 . 1.365(2) ?
C28 C31 . 1.491(3) ?
C29 H29A . 0.9600 ?
C29 H29B . 0.9600 ?
C29 H29C . 0.9600 ?
C30 H30A . 0.9600 ?
C30 H30B . 0.9600 ?
C30 H30C . 0.9600 ?
C32 C33 . 1.377(2) ?
C32 C37 . 1.376(2) ?
C33 H33 . 0.9300 ?
C33 C34 . 1.383(2) ?
C34 H34 . 0.9300 ?
C34 C35 . 1.381(2) ?
C35 C36 . 1.383(3) ?
C36 H36 . 0.9300 ?
C36 C37 . 1.384(2) ?
C37 H37 . 0.9300 ?
C38 C39 . 1.385(2) ?
C38 C42 . 1.376(2) ?
C39 H39 . 0.9300 ?
C39 C40 . 1.369(2) ?
C40 H40 . 0.9300 ?
C41 C42 . 1.378(2) ?
C41 C43 . 1.509(3) ?
C42 H42 . 0.9300 ?
C44 H44B . 0.9600 ?
C44 H44C . 0.9600 ?
C44 H44A . 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
N1 H1 O4 2_656 0.86 2.12 2.941(2) 159
N3 H3 O7 1_545 0.86 2.22 2.922(2) 138
N4 H4 O8 2_767 0.86 2.15 2.985(2) 163
N6 H6 O3 1_566 0.86 2.30 2.957(2) 133
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
S1 C35 C36 C37 . . . . -177.77(14) ?
S1 C38 C39 C40 . . . . 179.83(17) ?
S1 C38 C42 C41 . . . . -179.13(15) ?
O1 C2 C3 C4 . . . . 179.82(17) ?
O2 C4 C5 C6 . . . . -178.31(19) ?
N1 C10 C11 C12 . . . . 179.40(19) ?
N1 C10 C15 C14 . . . . -179.2(2) ?
N2 C19 C20 C16 . . . . -2.2(3) ?
N2 C19 C21 O4 . . . . -177.59(19) ?
N2 C19 C21 N3 . . . . 3.5(3) ?
C1 C2 C3 C4 . . . . -1.8(3) ?
C1 C6 C9 O3 . . . . -149.3(2) ?
C1 C6 C9 N1 . . . . 32.3(3) ?
C2 C1 C6 C5 . . . . 2.1(3) ?
C2 C1 C6 C9 . . . . -176.02(18) ?
C2 C3 C4 O2 . . . . -179.76(18) ?
C2 C3 C4 C5 . . . . 2.2(3) ?
C3 C4 C5 C6 . . . . -0.5(3) ?
C4 C5 C6 C1 . . . . -1.7(3) ?
C4 C5 C6 C9 . . . . 176.49(19) ?
C5 C6 C9 O3 . . . . 32.5(3) ?
C5 C6 C9 N1 . . . . -145.87(19) ?
C6 C1 C2 O1 . . . . 178.23(15) ?
C6 C1 C2 C3 . . . . -0.3(3) ?
C7 O1 C2 C1 . . . . -177.90(17) ?
C7 O1 C2 C3 . . . . 0.6(3) ?
C8 O2 C4 C3 . . . . 177.17(18) ?
C8 O2 C4 C5 . . . . -4.8(3) ?
C9 N1 C10 C11 . . . . 36.4(3) ?
C9 N1 C10 C15 . . . . -145.8(2) ?
C10 N1 C9 O3 . . . . 4.0(4) ?
C10 N1 C9 C6 . . . . -177.61(19) ?
C10 C11 C12 C13 . . . . -0.7(3) ?
C11 C10 C15 C14 . . . . -1.3(3) ?
C11 C12 C13 C14 . . . . -0.6(3) ?
C11 C12 C13 S2 . . . . -178.15(16) ?
C12 C13 C14 C15 . . . . 0.9(3) ?
C12 C13 S2 C16 . . . . -68.06(18) ?
C13 C14 C15 C10 . . . . 0.1(3) ?
C14 C13 S2 C16 . . . . 114.47(18) ?
C15 C10 C11 C12 . . . . 1.6(3) ?
C16 C17 C18 N2 . . . . -0.3(4) ?
C17 C16 C20 C19 . . . . 1.8(3) ?
C17 C16 S2 C13 . . . . 161.70(16) ?
C18 N2 C19 C20 . . . . 1.3(3) ?
C18 N2 C19 C21 . . . . -177.12(18) ?
C19 N2 C18 C17 . . . . 0.0(3) ?
C20 C16 C17 C18 . . . . -0.6(3) ?
C20 C16 S2 C13 . . . . -19.4(2) ?
C20 C19 C21 O4 . . . . 3.9(3) ?
C20 C19 C21 N3 . . . . -174.95(17) ?
C21 C19 C20 C16 . . . . 176.16(17) ?
C22 N3 C21 O4 . . . . -3.2(3) ?
C22 N3 C21 C19 . . . . 175.66(17) ?
S2 C13 C14 C15 . . . . 178.39(16) ?
S2 C16 C17 C18 . . . . 178.32(16) ?
S2 C16 C20 C19 . . . . -177.09(14) ?
O5 C24 C25 C26 . . . . 179.0(2) ?
O6 C26 C27 C28 . . . . -179.1(2) ?
N4 C32 C33 C34 . . . . -179.35(17) ?
N4 C32 C37 C36 . . . . 179.74(17) ?
N5 C41 C42 C38 . . . . -1.4(3) ?
N5 C41 C43 O8 . . . . 174.55(19) ?
N5 C41 C43 N6 . . . . -5.3(3) ?
C23 C24 C25 C26 . . . . -0.8(4) ?
C23 C28 C31 O7 . . . . 34.5(3) ?
C23 C28 C31 N4 . . . . -144.92(19) ?
C24 C23 C28 C27 . . . . -2.4(3) ?
C24 C23 C28 C31 . . . . 179.0(2) ?
C24 C25 C26 O6 . . . . 179.3(2) ?
C24 C25 C26 C27 . . . . -1.1(4) ?
C25 C26 C27 C28 . . . . 1.3(3) ?
C26 C27 C28 C23 . . . . 0.5(3) ?
C26 C27 C28 C31 . . . . 179.1(2) ?
C27 C28 C31 O7 . . . . -144.2(2) ?
C27 C28 C31 N4 . . . . 36.4(3) ?
C28 C23 C24 O5 . . . . -177.3(2) ?
C28 C23 C24 C25 . . . . 2.5(3) ?
C29 O5 C24 C23 . . . . 0.6(4) ?
C29 O5 C24 C25 . . . . -179.1(2) ?
C30 O6 C26 C25 . . . . 2.2(4) ?
C30 O6 C26 C27 . . . . -177.3(2) ?
C31 N4 C32 C33 . . . . -139.0(2) ?
C31 N4 C32 C37 . . . . 44.2(3) ?
C32 N4 C31 O7 . . . . 5.9(3) ?
C32 N4 C31 C28 . . . . -174.73(18) ?
C32 C33 C34 C35 . . . . 0.5(3) ?
C33 C32 C37 C36 . . . . 2.9(3) ?
C33 C34 C35 S1 . . . . 178.18(15) ?
C33 C34 C35 C36 . . . . 1.1(3) ?
C34 C35 C36 C37 . . . . -0.7(3) ?
C35 S1 C38 C39 . . . . 175.66(17) ?
C35 S1 C38 C42 . . . . -5.7(2) ?
C35 C36 C37 C32 . . . . -1.4(3) ?
C37 C32 C33 C34 . . . . -2.5(3) ?
C38 S1 C35 C34 . . . . 96.53(17) ?
C38 S1 C35 C36 . . . . -86.45(18) ?
C38 C39 C40 N5 . . . . 0.1(3) ?
C39 C38 C42 C41 . . . . -0.5(3) ?
C40 N5 C41 C42 . . . . 2.5(3) ?
C40 N5 C41 C43 . . . . -174.82(18) ?
C41 N5 C40 C39 . . . . -1.8(3) ?
C42 C38 C39 C40 . . . . 1.1(3) ?
C42 C41 C43 O8 . . . . -2.9(3) ?
C42 C41 C43 N6 . . . . 177.22(19) ?
C43 C41 C42 C38 . . . . 175.86(17) ?
C44 N6 C43 O8 . . . . -3.8(3) ?
C44 N6 C43 C41 . . . . 176.07(17) ?
