#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/11/7201161.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7201161
loop_
_publ_author_name
'Nauha, Elisa'
'Saxell, Heidi'
'Nissinen, Maija'
'Kolehmainen, Erkki'
'Schäfer, Ansgar'
'Schlecker, Rainer'
_publ_section_title
;
 Polymorphism and versatile solvate formation of thiophanate-methyl
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              2536
_journal_paper_doi               10.1039/b905511h
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         '2 C12 H14 N4 O4 S2, C6 H10 O'
_chemical_formula_sum            'C30 H38 N8 O9 S4'
_chemical_formula_weight         782.92
_chemical_name_common            'thiophanate-methyl, cyclohexanone'
_chemical_name_systematic
;
?
;
_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                92.210(12)
_cell_angle_beta                 103.760(11)
_cell_angle_gamma                100.772(10)
_cell_formula_units_Z            4
_cell_length_a                   11.277(3)
_cell_length_b                   17.368(4)
_cell_length_c                   19.902(5)
_cell_measurement_temperature    103(2)
_cell_volume                     3705.3(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.896
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_device_type  'Bruker AXS CCD Detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0651
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28524
_diffrn_reflns_theta_full        57.68
_diffrn_reflns_theta_max         57.68
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    2.885
_exptl_absorpt_correction_T_max  0.4782
_exptl_absorpt_correction_T_min  0.3265
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'R.H. Blessing, Acta Cryst. A 1995, 51, 33'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.00030(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     976
_refine_ls_number_reflns         9162
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0411
_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)+(0.0449P)²+0.9447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1040
_reflns_number_gt                6713
_reflns_number_total             9162
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b905511h.txt
_cod_data_source_block           TM_cyclohexanone
_cod_original_cell_volume        3705.2(14)
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               7201161
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.33365(7) 0.07390(5) 0.90681(4) 0.0255(2) Uani 1 1 d . . .
S2 S 0.02420(7) 0.32733(5) 0.80680(4) 0.0282(2) Uani 1 1 d . . .
S3 S 0.31630(7) 0.66424(5) 0.41196(4) 0.0272(2) Uani 1 1 d . . .
S4 S 0.77952(7) 0.89397(5) 0.57147(4) 0.0275(2) Uani 1 1 d . . .
S5 S 0.53163(8) 0.33952(5) 0.30888(4) 0.0310(2) Uani 1 1 d . . .
S6 S 0.84248(7) 0.09683(5) 0.39683(4) 0.0257(2) Uani 1 1 d . . .
S7 S 1.21396(8) 0.35300(5) 0.06867(4) 0.0302(2) Uani 1 1 d . . .
S8 S 0.72153(7) 0.09834(5) -0.06544(4) 0.0294(2) Uani 1 1 d . . .
O1 O 0.62809(19) 0.17622(12) 0.77773(10) 0.0256(5) Uani 1 1 d . . .
O2 O 0.43329(19) 0.17945(12) 0.71535(11) 0.0259(5) Uani 1 1 d . . .
O3 O 0.38963(19) 0.27750(13) 0.93750(11) 0.0351(6) Uani 1 1 d . . .
O4 O 0.4341(2) 0.40983(12) 0.95636(11) 0.0344(6) Uani 1 1 d . . .
O5 O 0.64081(19) 0.55754(12) 0.55681(11) 0.0301(6) Uani 1 1 d . . .
O6 O 0.7027(2) 0.68953(14) 0.55856(12) 0.0411(7) Uani 1 1 d . . .
O7 O 1.02487(19) 0.82234(12) 0.42207(10) 0.0249(5) Uani 1 1 d . . .
O8 O 0.83367(19) 0.82969(12) 0.35773(11) 0.0260(5) Uani 1 1 d . . .
O9 O 0.88984(19) 0.42290(12) 0.50080(11) 0.0290(6) Uani 1 1 d . . .
O10 O 0.8707(2) 0.29396(13) 0.46896(11) 0.0340(6) Uani 1 1 d . . .
O11 O 0.95443(19) 0.21211(12) 0.21229(11) 0.0265(5) Uani 1 1 d . . .
O12 O 1.14637(19) 0.20124(12) 0.27358(10) 0.0258(5) Uani 1 1 d . . .
O13 O 0.88768(19) 0.44730(12) -0.08548(11) 0.0350(6) Uani 1 1 d . . .
O14 O 0.8189(2) 0.31944(14) -0.07165(12) 0.0376(6) Uani 1 1 d . . .
O15 O 0.48814(19) 0.19572(12) 0.07939(10) 0.0255(5) Uani 1 1 d . . .
O16 O 0.6925(2) 0.22130(12) 0.13511(11) 0.0276(6) Uani 1 1 d . . .
O17 O 0.3035(2) 0.46638(12) 0.58414(11) 0.0337(6) Uani 1 1 d . . .
O18 O 0.82203(19) 0.49108(12) 0.08556(11) 0.0283(6) Uani 1 1 d . . .
N1 N 0.4715(2) 0.13222(14) 0.82372(13) 0.0210(6) Uani 1 1 d D . .
H1 H 0.538(2) 0.1259(16) 0.8563(12) 0.025 Uiso 1 1 d D . .
N2 N 0.2589(2) 0.12369(14) 0.78148(13) 0.0207(6) Uani 1 1 d D . .
H2 H 0.279(3) 0.1440(16) 0.7441(12) 0.025 Uiso 1 1 d D . .
N3 N 0.1623(2) 0.22238(15) 0.85898(13) 0.0202(6) Uani 1 1 d D . .
H3 H 0.2358(19) 0.2159(16) 0.8855(13) 0.024 Uiso 1 1 d D . .
N4 N 0.2446(2) 0.35287(15) 0.89492(13) 0.0246(7) Uani 1 1 d D . .
H4 H 0.231(3) 0.4023(12) 0.8968(15) 0.030 Uiso 1 1 d D . .
N5 N 0.5055(3) 0.62479(15) 0.49959(14) 0.0243(7) Uani 1 1 d D . .
H5 H 0.452(2) 0.5780(12) 0.4862(14) 0.029 Uiso 1 1 d D . .
N6 N 0.5196(2) 0.75912(15) 0.49337(13) 0.0229(7) Uani 1 1 d D . .
H6 H 0.5949(19) 0.7646(17) 0.5216(13) 0.028 Uiso 1 1 d D . .
N7 N 0.6835(2) 0.86392(14) 0.43520(13) 0.0202(6) Uani 1 1 d D . .
H7 H 0.700(3) 0.8512(16) 0.3949(11) 0.024 Uiso 1 1 d D . .
N8 N 0.8921(2) 0.85807(15) 0.47634(13) 0.0223(7) Uani 1 1 d D . .
H8 H 0.954(2) 0.8607(17) 0.5132(11) 0.027 Uiso 1 1 d D . .
N9 N 0.7306(2) 0.36675(15) 0.41396(13) 0.0229(7) Uani 1 1 d D . .
H9 H 0.714(3) 0.4156(12) 0.4125(15) 0.027 Uiso 1 1 d D . .
N10 N 0.6696(2) 0.23755(15) 0.36540(12) 0.0204(6) Uani 1 1 d D . .
H10 H 0.735(2) 0.2271(17) 0.3968(12) 0.024 Uiso 1 1 d D . .
N11 N 0.7762(2) 0.15760(14) 0.27620(13) 0.0210(6) Uani 1 1 d D . .
H11 H 0.801(3) 0.1797(16) 0.2421(12) 0.025 Uiso 1 1 d D . .
N12 N 0.9876(2) 0.16309(15) 0.31983(13) 0.0216(6) Uani 1 1 d D . .
H12 H 1.048(2) 0.1482(16) 0.3508(12) 0.026 Uiso 1 1 d D . .
N13 N 1.0177(3) 0.38620(15) -0.01728(14) 0.0254(7) Uani 1 1 d D . .
H13 H 1.072(2) 0.4305(12) -0.0129(15) 0.030 Uiso 1 1 d D . .
N14 N 0.9982(2) 0.25566(16) 0.00393(13) 0.0234(7) Uani 1 1 d D . .
H14 H 0.9195(18) 0.2499(17) -0.0230(13) 0.028 Uiso 1 1 d D . .
N15 N 0.8314(2) 0.15781(14) 0.06368(13) 0.0208(6) Uani 1 1 d D . .
H15 H 0.822(3) 0.1794(15) 0.1026(11) 0.025 Uiso 1 1 d D . .
N16 N 0.6184(2) 0.15457(15) 0.02625(13) 0.0231(7) Uani 1 1 d D . .
H16 H 0.547(2) 0.1392(16) -0.0064(12) 0.028 Uiso 1 1 d D . .
C1 C 0.6778(3) 0.21453(19) 0.72404(16) 0.0301(9) Uani 1 1 d . . .
H1A H 0.6608 0.1770 0.6832 0.045 Uiso 1 1 calc R . .
H1B H 0.7680 0.2332 0.7414 0.045 Uiso 1 1 calc R . .
H1C H 0.6381 0.2593 0.7112 0.045 Uiso 1 1 calc R . .
C2 C 0.5050(3) 0.16431(17) 0.76691(18) 0.0226(8) Uani 1 1 d . . .
C3 C 0.3527(3) 0.11201(17) 0.83317(16) 0.0217(8) Uani 1 1 d . . .
C4 C 0.1303(3) 0.10539(18) 0.78230(15) 0.0203(8) Uani 1 1 d . . .
C5 C 0.0530(3) 0.04066(18) 0.74164(16) 0.0252(8) Uani 1 1 d . . .
H5A H 0.0868 0.0068 0.7161 0.030 Uiso 1 1 calc R . .
C6 C -0.0740(3) 0.02464(18) 0.73779(16) 0.0257(8) Uani 1 1 d . . .
H6A H -0.1270 -0.0195 0.7091 0.031 Uiso 1 1 calc R . .
C7 C -0.1228(3) 0.07316(18) 0.77580(16) 0.0235(8) Uani 1 1 d . . .
H7A H -0.2094 0.0622 0.7737 0.028 Uiso 1 1 calc R . .
C8 C -0.0452(3) 0.13803(17) 0.81705(15) 0.0219(8) Uani 1 1 d . . .
H8A H -0.0787 0.1708 0.8438 0.026 Uiso 1 1 calc R . .
C9 C 0.0804(3) 0.15523(18) 0.81938(15) 0.0200(8) Uani 1 1 d . . .
C10 C 0.1471(3) 0.29706(19) 0.85495(15) 0.0225(8) Uani 1 1 d . . .
C11 C 0.3594(3) 0.3404(2) 0.93092(16) 0.0284(9) Uani 1 1 d . . .
C12 C 0.5569(3) 0.4048(2) 0.99739(19) 0.0517(11) Uani 1 1 d . . .
H12A H 0.5504 0.3862 1.0425 0.078 Uiso 1 1 calc R . .
H12B H 0.6117 0.4569 1.0045 0.078 Uiso 1 1 calc R . .
H12C H 0.5915 0.3679 0.9729 0.078 Uiso 1 1 calc R . .
C13 C 0.7672(3) 0.5574(2) 0.59755(19) 0.0484(11) Uani 1 1 d . . .
H13A H 0.8270 0.5759 0.5703 0.073 Uiso 1 1 calc R . .
H13B H 0.7734 0.5038 0.6095 0.073 Uiso 1 1 calc R . .
H13C H 0.7859 0.5922 0.6402 0.073 Uiso 1 1 calc R . .
C14 C 0.6252(4) 0.6301(2) 0.54078(17) 0.0288(9) Uani 1 1 d . . .
C15 C 0.4529(3) 0.68696(19) 0.47084(15) 0.0229(8) Uani 1 1 d . . .
C16 C 0.4850(3) 0.82980(17) 0.46809(15) 0.0202(8) Uani 1 1 d . . .
C17 C 0.3724(3) 0.84840(17) 0.47207(15) 0.0228(8) Uani 1 1 d . . .
H17 H 0.3178 0.8145 0.4929 0.027 Uiso 1 1 calc R . .
C18 C 0.3393(3) 0.91609(18) 0.44587(15) 0.0224(8) Uani 1 1 d . . .
H18 H 0.2619 0.9285 0.4485 0.027 Uiso 1 1 calc R . .
C19 C 0.4189(3) 0.96564(18) 0.41590(16) 0.0242(8) Uani 1 1 d . . .
H19 H 0.3952 1.0115 0.3970 0.029 Uiso 1 1 calc R . .
C20 C 0.5329(3) 0.94862(18) 0.41330(15) 0.0231(8) Uani 1 1 d . . .
H20 H 0.5882 0.9832 0.3934 0.028 Uiso 1 1 calc R . .
C21 C 0.5662(3) 0.88081(17) 0.43996(15) 0.0191(8) Uani 1 1 d . . .
C22 C 0.7826(3) 0.87136(17) 0.48911(16) 0.0207(8) Uani 1 1 d . . .
C23 C 0.9103(3) 0.83615(17) 0.41303(18) 0.0220(8) Uani 1 1 d . . .
C24 C 1.0531(3) 0.79141(18) 0.36019(16) 0.0282(9) Uani 1 1 d . . .
H24A H 0.9838 0.7495 0.3355 0.042 Uiso 1 1 calc R . .
H24B H 1.1293 0.7702 0.3734 0.042 Uiso 1 1 calc R . .
H24C H 1.0655 0.8337 0.3298 0.042 Uiso 1 1 calc R . .
C25 C 0.9940(3) 0.41656(19) 0.55761(17) 0.0392(10) Uani 1 1 d . . .
H25A H 0.9657 0.3780 0.5881 0.059 Uiso 1 1 calc R . .
H25B H 1.0279 0.4679 0.5841 0.059 Uiso 1 1 calc R . .
H25C H 1.0589 0.3994 0.5391 0.059 Uiso 1 1 calc R . .
C26 C 0.8344(3) 0.3549(2) 0.46241(16) 0.0249(8) Uani 1 1 d . . .
C27 C 0.6479(3) 0.31054(19) 0.36452(16) 0.0225(8) Uani 1 1 d . . .
C28 C 0.5936(3) 0.17380(17) 0.31774(16) 0.0201(8) Uani 1 1 d . . .
C29 C 0.4678(3) 0.15069(17) 0.31418(16) 0.0226(8) Uani 1 1 d . . .
H29 H 0.4318 0.1758 0.3452 0.027 Uiso 1 1 calc R . .
C30 C 0.3946(3) 0.09124(18) 0.26568(17) 0.0269(8) Uani 1 1 d . . .
H30 H 0.3079 0.0765 0.2626 0.032 Uiso 1 1 calc R . .
C31 C 0.4471(3) 0.05301(18) 0.22158(17) 0.0293(9) Uani 1 1 d . . .
H31 H 0.3964 0.0124 0.1880 0.035 Uiso 1 1 calc R . .
C32 C 0.5736(3) 0.07406(18) 0.22649(16) 0.0260(8) Uani 1 1 d . . .
H32 H 0.6101 0.0471 0.1968 0.031 Uiso 1 1 calc R . .
C33 C 0.6473(3) 0.13436(17) 0.27458(16) 0.0185(8) Uani 1 1 d . . .
C34 C 0.8674(3) 0.14151(17) 0.32693(16) 0.0223(8) Uani 1 1 d . . .
C35 C 1.0241(3) 0.19404(17) 0.26341(17) 0.0238(8) Uani 1 1 d . . .
C36 C 1.1978(3) 0.23267(19) 0.21767(16) 0.0286(9) Uani 1 1 d . . .
H36A H 1.1754 0.1926 0.1783 0.043 Uiso 1 1 calc R . .
H36B H 1.2888 0.2475 0.2339 0.043 Uiso 1 1 calc R . .
H36C H 1.1640 0.2791 0.2030 0.043 Uiso 1 1 calc R . .
C37 C 0.7734(3) 0.4442(2) -0.13804(18) 0.0461(11) Uani 1 1 d . . .
H37A H 0.7675 0.4050 -0.1761 0.069 Uiso 1 1 calc R . .
H37B H 0.7730 0.4960 -0.1560 0.069 Uiso 1 1 calc R . .
H37C H 0.7021 0.4296 -0.1177 0.069 Uiso 1 1 calc R . .
C38 C 0.8994(4) 0.3780(2) -0.05980(17) 0.0309(9) Uani 1 1 d . . .
C39 C 1.0714(3) 0.32778(19) 0.01689(16) 0.0251(8) Uani 1 1 d . . .
C40 C 1.0302(3) 0.18518(17) 0.03091(15) 0.0201(8) Uani 1 1 d . . .
C41 C 1.1403(3) 0.16303(18) 0.02640(15) 0.0241(8) Uani 1 1 d . . .
H41 H 1.1974 0.1958 0.0063 0.029 Uiso 1 1 calc R . .
C42 C 1.1670(3) 0.09319(18) 0.05120(15) 0.0241(8) Uani 1 1 d . . .
H42 H 1.2427 0.0782 0.0485 0.029 Uiso 1 1 calc R . .
C43 C 1.0836(3) 0.04563(18) 0.07982(16) 0.0251(8) Uani 1 1 d . . .
H43 H 1.1024 -0.0021 0.0971 0.030 Uiso 1 1 calc R . .
C44 C 0.9730(3) 0.06646(18) 0.08371(15) 0.0229(8) Uani 1 1 d . . .
H44 H 0.9156 0.0331 0.1032 0.027 Uiso 1 1 calc R . .
C45 C 0.9462(3) 0.13652(18) 0.05891(15) 0.0182(8) Uani 1 1 d . . .
C46 C 0.7263(3) 0.13880(17) 0.01306(16) 0.0215(8) Uani 1 1 d . . .
C47 C 0.6063(3) 0.19309(18) 0.08536(18) 0.0225(8) Uani 1 1 d . . .
C48 C 0.4623(3) 0.23847(18) 0.13681(16) 0.0288(9) Uani 1 1 d . . .
H48A H 0.4827 0.2112 0.1790 0.043 Uiso 1 1 calc R . .
H48B H 0.3738 0.2411 0.1258 0.043 Uiso 1 1 calc R . .
H48C H 0.5130 0.2919 0.1444 0.043 Uiso 1 1 calc R . .
C49 C 0.4943(3) 0.46233(19) 0.66736(16) 0.0282(9) Uani 1 1 d . . .
H49A H 0.5216 0.5166 0.6557 0.034 Uiso 1 1 calc R . .
H49B H 0.5515 0.4298 0.6561 0.034 Uiso 1 1 calc R . .
C50 C 0.4981(3) 0.46251(19) 0.74472(16) 0.0328(9) Uani 1 1 d . . .
H50A H 0.5851 0.4814 0.7723 0.039 Uiso 1 1 calc R . .
H50B H 0.4474 0.4993 0.7564 0.039 Uiso 1 1 calc R . .
C51 C 0.4491(3) 0.38138(19) 0.76378(17) 0.0351(9) Uani 1 1 d . . .
H51A H 0.4499 0.3840 0.8137 0.042 Uiso 1 1 calc R . .
H51B H 0.5042 0.3456 0.7560 0.042 Uiso 1 1 calc R . .
C52 C 0.3168(3) 0.34871(19) 0.72068(16) 0.0329(9) Uani 1 1 d . . .
H52A H 0.2599 0.3812 0.7324 0.040 Uiso 1 1 calc R . .
H52B H 0.2890 0.2944 0.7321 0.040 Uiso 1 1 calc R . .
C53 C 0.3101(3) 0.34854(18) 0.64265(17) 0.0335(9) Uani 1 1 d . . .
H53A H 0.3571 0.3102 0.6294 0.040 Uiso 1 1 calc R . .
H53B H 0.2222 0.3326 0.6156 0.040 Uiso 1 1 calc R . .
C54 C 0.3646(3) 0.42968(19) 0.62630(17) 0.0293(9) Uani 1 1 d . . .
C55 C 0.8357(3) 0.45268(18) 0.13596(17) 0.0268(8) Uani 1 1 d . . .
C56 C 0.9324(3) 0.40292(19) 0.15157(16) 0.0310(9) Uani 1 1 d . . .
H56A H 0.9912 0.4159 0.1219 0.037 Uiso 1 1 calc R . .
H56B H 0.8913 0.3468 0.1401 0.037 Uiso 1 1 calc R . .
C57 C 1.0049(3) 0.4153(2) 0.22763(17) 0.0377(10) Uani 1 1 d . . .
H57A H 1.0601 0.3769 0.2370 0.045 Uiso 1 1 calc R . .
H57B H 1.0579 0.4688 0.2371 0.045 Uiso 1 1 calc R . .
C58 C 0.9181(3) 0.4057(2) 0.27574(17) 0.0362(9) Uani 1 1 d . . .
H58A H 0.9677 0.4149 0.3246 0.043 Uiso 1 1 calc R . .
H58B H 0.8685 0.3513 0.2684 0.043 Uiso 1 1 calc R . .
C59 C 0.8308(3) 0.46350(19) 0.26219(16) 0.0346(9) Uani 1 1 d . . .
H59A H 0.8800 0.5180 0.2726 0.042 Uiso 1 1 calc R . .
H59B H 0.7734 0.4555 0.2931 0.042 Uiso 1 1 calc R . .
C60 C 0.7550(3) 0.4516(2) 0.18578(16) 0.0328(9) Uani 1 1 d . . .
H60A H 0.6952 0.4006 0.1780 0.039 Uiso 1 1 calc R . .
H60B H 0.7065 0.4937 0.1765 0.039 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 115.2(2) . . ?
C11 O4 C12 114.7(3) . . ?
C14 O5 C13 112.3(3) . . ?
C23 O7 C24 115.2(2) . . ?
C26 O9 C25 114.1(2) . . ?
C35 O12 C36 115.4(2) . . ?
C38 O13 C37 113.9(3) . . ?
C47 O15 C48 115.6(2) . . ?
C3 N1 C2 127.1(3) . . ?
C3 N2 C4 124.4(3) . . ?
C10 N3 C9 125.9(3) . . ?
C10 N4 C11 126.7(3) . . ?
C14 N5 C15 126.7(3) . . ?
C15 N6 C16 124.2(3) . . ?
C22 N7 C21 124.0(3) . . ?
C23 N8 C22 126.5(3) . . ?
C26 N9 C27 126.5(3) . . ?
C27 N10 C28 123.0(3) . . ?
C34 N11 C33 123.1(3) . . ?
C34 N12 C35 127.1(3) . . ?
C38 N13 C39 127.4(3) . . ?
C39 N14 C40 126.2(3) . . ?
C46 N15 C45 123.2(3) . . ?
C46 N16 C47 127.2(3) . . ?
O2 C2 O1 125.6(3) . . ?
O2 C2 N1 125.5(3) . . ?
O1 C2 N1 109.0(3) . . ?
N2 C3 N1 116.9(3) . . ?
N2 C3 S1 124.1(2) . . ?
N1 C3 S1 118.9(2) . . ?
C5 C4 C9 119.7(3) . . ?
C5 C4 N2 119.3(3) . . ?
C9 C4 N2 120.8(3) . . ?
C4 C5 C6 120.5(3) . . ?
C7 C6 C5 119.7(3) . . ?
C6 C7 C8 120.0(3) . . ?
C9 C8 C7 120.4(3) . . ?
C8 C9 C4 119.7(3) . . ?
C8 C9 N3 122.2(3) . . ?
C4 C9 N3 118.1(3) . . ?
N3 C10 N4 115.1(3) . . ?
N3 C10 S2 126.4(3) . . ?
N4 C10 S2 118.5(2) . . ?
O3 C11 O4 124.8(3) . . ?
O3 C11 N4 126.0(3) . . ?
O4 C11 N4 109.2(3) . . ?
O6 C14 O5 125.6(3) . . ?
O6 C14 N5 125.7(3) . . ?
O5 C14 N5 108.7(3) . . ?
N6 C15 N5 115.7(3) . . ?
N6 C15 S3 126.5(2) . . ?
N5 C15 S3 117.8(2) . . ?
C21 C16 C17 119.6(3) . . ?
C21 C16 N6 119.3(3) . . ?
C17 C16 N6 121.1(3) . . ?
C18 C17 C16 120.3(3) . . ?
C19 C18 C17 120.0(3) . . ?
C18 C19 C20 120.2(3) . . ?
C19 C20 C21 119.7(3) . . ?
C16 C21 C20 120.2(3) . . ?
C16 C21 N7 121.3(3) . . ?
C20 C21 N7 118.4(3) . . ?
N7 C22 N8 117.9(3) . . ?
N7 C22 S4 123.5(2) . . ?
N8 C22 S4 118.6(2) . . ?
O8 C23 O7 125.4(3) . . ?
O8 C23 N8 125.5(3) . . ?
O7 C23 N8 109.2(3) . . ?
O10 C26 O9 125.2(3) . . ?
O10 C26 N9 126.0(3) . . ?
O9 C26 N9 108.8(3) . . ?
N10 C27 N9 116.5(3) . . ?
N10 C27 S5 125.5(2) . . ?
N9 C27 S5 118.0(2) . . ?
C29 C28 C33 119.7(3) . . ?
C29 C28 N10 121.0(3) . . ?
C33 C28 N10 119.2(3) . . ?
C30 C29 C28 120.2(3) . . ?
C29 C30 C31 120.2(3) . . ?
C30 C31 C32 119.8(3) . . ?
C31 C32 C33 120.2(3) . . ?
C32 C33 C28 119.8(3) . . ?
C32 C33 N11 119.0(3) . . ?
C28 C33 N11 121.1(3) . . ?
N11 C34 N12 117.0(3) . . ?
N11 C34 S6 123.6(2) . . ?
N12 C34 S6 119.4(2) . . ?
O11 C35 O12 125.5(3) . . ?
O11 C35 N12 125.1(3) . . ?
O12 C35 N12 109.4(3) . . ?
O14 C38 O13 125.2(3) . . ?
O14 C38 N13 126.5(3) . . ?
O13 C38 N13 108.3(3) . . ?
N14 C39 N13 114.5(3) . . ?
N14 C39 S7 127.0(2) . . ?
N13 C39 S7 118.5(2) . . ?
C45 C40 C41 119.8(3) . . ?
C45 C40 N14 118.7(3) . . ?
C41 C40 N14 121.4(3) . . ?
C42 C41 C40 120.1(3) . . ?
C43 C42 C41 119.7(3) . . ?
C42 C43 C44 120.7(3) . . ?
C43 C44 C45 119.5(3) . . ?
C40 C45 C44 120.1(3) . . ?
C40 C45 N15 120.8(3) . . ?
C44 C45 N15 119.0(3) . . ?
N15 C46 N16 118.2(3) . . ?
N15 C46 S8 122.8(2) . . ?
N16 C46 S8 119.1(2) . . ?
O16 C47 O15 125.5(3) . . ?
O16 C47 N16 124.9(3) . . ?
O15 C47 N16 109.6(3) . . ?
C54 C49 C50 109.0(3) . . ?
C51 C50 C49 111.6(3) . . ?
C50 C51 C52 111.2(3) . . ?
C51 C52 C53 111.0(3) . . ?
C54 C53 C52 109.7(3) . . ?
O17 C54 C49 123.4(3) . . ?
O17 C54 C53 121.8(3) . . ?
C49 C54 C53 114.7(3) . . ?
O18 C55 C60 121.8(3) . . ?
O18 C55 C56 122.6(3) . . ?
C60 C55 C56 115.6(3) . . ?
C55 C56 C57 112.0(3) . . ?
C58 C57 C56 111.5(3) . . ?
C57 C58 C59 110.6(3) . . ?
C58 C59 C60 110.3(3) . . ?
C55 C60 C59 112.6(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C3 1.674(3) . ?
S2 C10 1.672(3) . ?
S3 C15 1.667(3) . ?
S4 C22 1.681(3) . ?
S5 C27 1.673(3) . ?
S6 C34 1.675(3) . ?
S7 C39 1.659(3) . ?
S8 C46 1.673(3) . ?
O1 C2 1.328(3) . ?
O1 C1 1.449(3) . ?
O2 C2 1.217(3) . ?
O3 C11 1.207(4) . ?
O4 C11 1.337(4) . ?
O4 C12 1.451(4) . ?
O5 C14 1.345(4) . ?
O5 C13 1.463(4) . ?
O6 C14 1.200(4) . ?
O7 C23 1.329(3) . ?
O7 C24 1.452(3) . ?
O8 C23 1.214(3) . ?
O9 C26 1.340(4) . ?
O9 C25 1.448(3) . ?
O10 C26 1.205(4) . ?
O11 C35 1.219(3) . ?
O12 C35 1.327(3) . ?
O12 C36 1.452(3) . ?
O13 C38 1.343(4) . ?
O13 C37 1.445(4) . ?
O14 C38 1.203(4) . ?
O15 C47 1.319(3) . ?
O15 C48 1.455(3) . ?
O16 C47 1.221(4) . ?
O17 C54 1.231(3) . ?
O18 C55 1.221(3) . ?
N1 C3 1.379(4) . ?
N1 C2 1.380(4) . ?
N2 C3 1.341(4) . ?
N2 C4 1.430(4) . ?
N3 C10 1.343(4) . ?
N3 C9 1.419(4) . ?
N4 C10 1.381(4) . ?
N4 C11 1.382(4) . ?
N5 C14 1.388(4) . ?
N5 C15 1.404(4) . ?
N6 C15 1.335(4) . ?
N6 C16 1.430(4) . ?
N7 C22 1.335(4) . ?
N7 C21 1.431(4) . ?
N8 C23 1.375(4) . ?
N8 C22 1.376(4) . ?
N9 C26 1.383(4) . ?
N9 C27 1.393(4) . ?
N10 C27 1.335(4) . ?
N10 C28 1.428(4) . ?
N11 C34 1.338(4) . ?
N11 C33 1.426(4) . ?
N12 C34 1.379(4) . ?
N12 C35 1.380(4) . ?
N13 C38 1.378(4) . ?
N13 C39 1.394(4) . ?
N14 C39 1.343(4) . ?
N14 C40 1.428(4) . ?
N15 C46 1.337(4) . ?
N15 C45 1.435(4) . ?
N16 C46 1.377(4) . ?
N16 C47 1.378(4) . ?
C4 C5 1.381(4) . ?
C4 C9 1.393(4) . ?
C5 C6 1.390(4) . ?
C6 C7 1.381(4) . ?
C7 C8 1.388(4) . ?
C8 C9 1.381(4) . ?
C16 C21 1.384(4) . ?
C16 C17 1.387(4) . ?
C17 C18 1.383(4) . ?
C18 C19 1.381(4) . ?
C19 C20 1.385(4) . ?
C20 C21 1.388(4) . ?
C28 C29 1.384(4) . ?
C28 C33 1.389(4) . ?
C29 C30 1.380(4) . ?
C30 C31 1.382(4) . ?
C31 C32 1.384(4) . ?
C32 C33 1.386(4) . ?
C40 C45 1.382(4) . ?
C40 C41 1.387(4) . ?
C41 C42 1.385(4) . ?
C42 C43 1.375(4) . ?
C43 C44 1.381(4) . ?
C44 C45 1.388(4) . ?
C49 C54 1.488(4) . ?
C49 C50 1.530(4) . ?
C50 C51 1.512(4) . ?
C51 C52 1.523(4) . ?
C52 C53 1.537(4) . ?
C53 C54 1.509(4) . ?
C55 C60 1.495(4) . ?
C55 C56 1.498(4) . ?
C56 C57 1.525(4) . ?
C57 C58 1.516(4) . ?
C58 C59 1.520(4) . ?
C59 C60 1.542(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.893(17) 1.96(2) 2.675(3) 136(2) .
N3 H3 O3 0.900(17) 1.89(2) 2.644(3) 139(2) .
N3 H3 S1 0.900(17) 2.89(2) 3.531(3) 129(2) .
N6 H6 O6 0.886(17) 1.99(2) 2.681(3) 134(3) .
N6 H6 S4 0.886(17) 2.73(2) 3.388(3) 132(2) .
N7 H7 O8 0.895(17) 1.92(2) 2.673(3) 141(2) .
N10 H10 O10 0.896(17) 1.98(2) 2.672(3) 133(2) .
N10 H10 S6 0.896(17) 2.76(2) 3.389(3) 128(2) .
N11 H11 O11 0.872(17) 1.95(2) 2.674(3) 140(2) .
N11 H11 O16 0.872(17) 2.40(2) 3.061(3) 133(2) .
N14 H14 O14 0.907(17) 1.94(2) 2.664(3) 136(2) .
N15 H15 O16 0.885(17) 1.97(2) 2.697(3) 138(2) .
N15 H15 O11 0.885(17) 2.32(2) 2.984(3) 132(2) .
N1 H1 S8 0.899(17) 2.411(18) 3.306(3) 174(2) 1_556
N2 H2 O8 0.893(17) 2.23(2) 2.921(3) 134(2) 2_666
N4 H4 O18 0.900(17) 2.092(18) 2.980(3) 168(3) 2_666
N5 H5 O5 0.905(17) 2.422(19) 3.302(3) 164(2) 2_666
N7 H7 O2 0.895(17) 2.32(2) 2.976(3) 130(2) 2_666
N8 H8 S6 0.879(17) 2.513(19) 3.364(3) 163(3) 2_766
N9 H9 O17 0.904(17) 2.095(18) 2.994(3) 173(3) 2_666
N12 H12 S4 0.890(17) 2.427(18) 3.316(3) 176(2) 2_766
N13 H13 O18 0.877(17) 2.40(2) 3.099(3) 138(2) 2_765
N13 H13 O13 0.877(17) 2.73(3) 3.322(4) 126(2) 2_765
N16 H16 S1 0.891(17) 2.631(18) 3.515(3) 171(3) 1_554
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 C2 O2 3.6(4) . . . . ?
C1 O1 C2 N1 -176.2(2) . . . . ?
C3 N1 C2 O2 -0.5(5) . . . . ?
C3 N1 C2 O1 179.3(3) . . . . ?
C4 N2 C3 N1 179.4(3) . . . . ?
C4 N2 C3 S1 0.1(4) . . . . ?
C2 N1 C3 N2 0.9(4) . . . . ?
C2 N1 C3 S1 -179.8(2) . . . . ?
C3 N2 C4 C5 -106.1(3) . . . . ?
C3 N2 C4 C9 78.7(4) . . . . ?
C9 C4 C5 C6 -0.4(4) . . . . ?
N2 C4 C5 C6 -175.6(3) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C6 C7 C8 C9 1.2(4) . . . . ?
C7 C8 C9 C4 -2.6(4) . . . . ?
C7 C8 C9 N3 177.8(3) . . . . ?
C5 C4 C9 C8 2.2(4) . . . . ?
N2 C4 C9 C8 177.3(3) . . . . ?
C5 C4 C9 N3 -178.2(3) . . . . ?
N2 C4 C9 N3 -3.1(4) . . . . ?
C10 N3 C9 C8 -54.0(4) . . . . ?
C10 N3 C9 C4 126.4(3) . . . . ?
C9 N3 C10 N4 -175.1(3) . . . . ?
C9 N3 C10 S2 4.6(4) . . . . ?
C11 N4 C10 N3 8.4(4) . . . . ?
C11 N4 C10 S2 -171.3(2) . . . . ?
C12 O4 C11 O3 -3.4(4) . . . . ?
C12 O4 C11 N4 178.1(3) . . . . ?
C10 N4 C11 O3 -6.0(5) . . . . ?
C10 N4 C11 O4 172.5(3) . . . . ?
C13 O5 C14 O6 -2.0(4) . . . . ?
C13 O5 C14 N5 177.2(2) . . . . ?
C15 N5 C14 O6 0.4(5) . . . . ?
C15 N5 C14 O5 -178.8(3) . . . . ?
C16 N6 C15 N5 176.9(3) . . . . ?
C16 N6 C15 S3 -2.2(4) . . . . ?
C14 N5 C15 N6 -9.7(4) . . . . ?
C14 N5 C15 S3 169.5(2) . . . . ?
C15 N6 C16 C21 -122.5(3) . . . . ?
C15 N6 C16 C17 58.3(4) . . . . ?
C21 C16 C17 C18 2.3(5) . . . . ?
N6 C16 C17 C18 -178.5(3) . . . . ?
C16 C17 C18 C19 -0.3(5) . . . . ?
C17 C18 C19 C20 -1.4(5) . . . . ?
C18 C19 C20 C21 1.0(5) . . . . ?
C17 C16 C21 C20 -2.6(5) . . . . ?
N6 C16 C21 C20 178.1(3) . . . . ?
C17 C16 C21 N7 179.7(3) . . . . ?
N6 C16 C21 N7 0.5(4) . . . . ?
C19 C20 C21 C16 1.0(5) . . . . ?
C19 C20 C21 N7 178.7(3) . . . . ?
C22 N7 C21 C16 -75.6(4) . . . . ?
C22 N7 C21 C20 106.7(3) . . . . ?
C21 N7 C22 N8 -175.8(3) . . . . ?
C21 N7 C22 S4 5.6(4) . . . . ?
C23 N8 C22 N7 -1.3(4) . . . . ?
C23 N8 C22 S4 177.4(2) . . . . ?
C24 O7 C23 O8 -4.9(4) . . . . ?
C24 O7 C23 N8 174.4(2) . . . . ?
C22 N8 C23 O8 4.7(5) . . . . ?
C22 N8 C23 O7 -174.7(3) . . . . ?
C25 O9 C26 O10 -5.9(4) . . . . ?
C25 O9 C26 N9 174.8(2) . . . . ?
C27 N9 C26 O10 0.9(5) . . . . ?
C27 N9 C26 O9 -179.8(3) . . . . ?
C28 N10 C27 N9 -179.6(3) . . . . ?
C28 N10 C27 S5 -0.3(4) . . . . ?
C26 N9 C27 N10 1.9(4) . . . . ?
C26 N9 C27 S5 -177.5(2) . . . . ?
C27 N10 C28 C29 -59.8(4) . . . . ?
C27 N10 C28 C33 120.5(3) . . . . ?
C33 C28 C29 C30 -3.1(4) . . . . ?
N10 C28 C29 C30 177.1(3) . . . . ?
C28 C29 C30 C31 1.7(4) . . . . ?
C29 C30 C31 C32 0.5(4) . . . . ?
C30 C31 C32 C33 -1.3(4) . . . . ?
C31 C32 C33 C28 -0.2(4) . . . . ?
C31 C32 C33 N11 -176.8(3) . . . . ?
C29 C28 C33 C32 2.4(4) . . . . ?
N10 C28 C33 C32 -177.9(3) . . . . ?
C29 C28 C33 N11 179.0(3) . . . . ?
N10 C28 C33 N11 -1.3(4) . . . . ?
C34 N11 C33 C32 -107.8(3) . . . . ?
C34 N11 C33 C28 75.6(4) . . . . ?
C33 N11 C34 N12 176.0(3) . . . . ?
C33 N11 C34 S6 -3.6(4) . . . . ?
C35 N12 C34 N11 -5.6(4) . . . . ?
C35 N12 C34 S6 174.1(2) . . . . ?
C36 O12 C35 O11 -0.7(4) . . . . ?
C36 O12 C35 N12 179.5(2) . . . . ?
C34 N12 C35 O11 5.3(5) . . . . ?
C34 N12 C35 O12 -174.9(3) . . . . ?
C37 O13 C38 O14 -8.5(5) . . . . ?
C37 O13 C38 N13 172.4(3) . . . . ?
C39 N13 C38 O14 4.6(5) . . . . ?
C39 N13 C38 O13 -176.3(3) . . . . ?
C40 N14 C39 N13 178.9(3) . . . . ?
C40 N14 C39 S7 -1.9(5) . . . . ?
C38 N13 C39 N14 2.3(4) . . . . ?
C38 N13 C39 S7 -177.0(2) . . . . ?
C39 N14 C40 C45 132.5(3) . . . . ?
C39 N14 C40 C41 -50.8(4) . . . . ?
C45 C40 C41 C42 -1.3(5) . . . . ?
N14 C40 C41 C42 -178.1(3) . . . . ?
C40 C41 C42 C43 0.5(5) . . . . ?
C41 C42 C43 C44 0.4(5) . . . . ?
C42 C43 C44 C45 -0.5(5) . . . . ?
C41 C40 C45 C44 1.3(5) . . . . ?
N14 C40 C45 C44 178.1(3) . . . . ?
C41 C40 C45 N15 -179.5(3) . . . . ?
N14 C40 C45 N15 -2.7(4) . . . . ?
C43 C44 C45 C40 -0.4(5) . . . . ?
C43 C44 C45 N15 -179.6(3) . . . . ?
C46 N15 C45 C40 89.1(4) . . . . ?
C46 N15 C45 C44 -91.7(4) . . . . ?
C45 N15 C46 N16 172.9(3) . . . . ?
C45 N15 C46 S8 -8.2(4) . . . . ?
C47 N16 C46 N15 4.5(4) . . . . ?
C47 N16 C46 S8 -174.5(2) . . . . ?
C48 O15 C47 O16 2.1(4) . . . . ?
C48 O15 C47 N16 -177.0(2) . . . . ?
C46 N16 C47 O16 2.0(5) . . . . ?
C46 N16 C47 O15 -178.9(3) . . . . ?
C54 C49 C50 C51 55.8(3) . . . . ?
C49 C50 C51 C52 -57.0(4) . . . . ?
C50 C51 C52 C53 55.5(4) . . . . ?
C51 C52 C53 C54 -53.3(3) . . . . ?
C50 C49 C54 O17 120.9(3) . . . . ?
C50 C49 C54 C53 -56.3(3) . . . . ?
C52 C53 C54 O17 -121.7(3) . . . . ?
C52 C53 C54 C49 55.6(4) . . . . ?
O18 C55 C56 C57 133.4(3) . . . . ?
C60 C55 C56 C57 -47.4(4) . . . . ?
C55 C56 C57 C58 52.1(4) . . . . ?
C56 C57 C58 C59 -58.4(4) . . . . ?
C57 C58 C59 C60 57.7(4) . . . . ?
O18 C55 C60 C59 -133.1(3) . . . . ?
C56 C55 C60 C59 47.7(4) . . . . ?
C58 C59 C60 C55 -52.0(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653605
