#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:33:12 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180342 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/11/7201158.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_7201158
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, C1 H4 O1'
_chemical_formula_sum            'C25 H32 N8 O9 S4'
_chemical_formula_weight         716.83
_chemical_name_common            'thiophanate-methyl, methanol'
_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                101.734(10)
_cell_angle_beta                 90.330(11)
_cell_angle_gamma                107.692(9)
_cell_formula_units_Z            2
_cell_length_a                   10.016(3)
_cell_length_b                   11.430(3)
_cell_length_c                   15.904(5)
_cell_measurement_temperature    103(2)
_cell_volume                     1693.9(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.838
_diffrn_measured_fraction_theta_max 0.838
_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  0.0606
_diffrn_reflns_av_sigmaI/netI    0.0789
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7892
_diffrn_reflns_theta_full        54.79
_diffrn_reflns_theta_max         54.79
_diffrn_reflns_theta_min         10.32
_exptl_absorpt_coefficient_mu    3.101
_exptl_absorpt_correction_T_max  0.8604
_exptl_absorpt_correction_T_min  0.7468
_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    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.0041(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         3543
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0726
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1121P)²+3.1676P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1975
_refine_ls_wR_factor_ref         0.2339
_reflns_number_gt                2428
_reflns_number_total             3543
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b905511h.txt
_cod_data_source_block           TM_MeOH
_cod_original_cell_volume        1694.0(9)
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               7201158
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 0.8544(2) 0.73682(19) 0.41812(14) 0.0674(7) Uani 1 1 d . . .
S2 S 1.0591(3) 0.4343(3) 0.11062(15) 0.1115(12) Uani 1 1 d . . .
S3 S 0.2280(2) 0.93911(17) 0.57554(13) 0.0629(7) Uani 1 1 d . . .
S4 S 0.4566(4) 0.7816(4) 0.87559(18) 0.1238(13) Uani 1 1 d . . .
O1 O 1.2171(6) 0.9472(5) 0.2814(4) 0.0670(15) Uani 1 1 d . . .
O2 O 1.1058(6) 1.0934(5) 0.3041(4) 0.0722(17) Uani 1 1 d . . .
O3 O 0.7248(8) 0.6230(7) 0.1856(5) 0.103(2) Uani 1 1 d . . .
O4 O 0.6939(7) 0.5977(7) 0.0432(4) 0.102(2) Uani 1 1 d . . .
O5 O 0.6196(5) 1.2376(4) 0.7183(4) 0.0653(15) Uani 1 1 d . . .
O6 O 0.5021(5) 1.3674(4) 0.6932(3) 0.0581(14) Uani 1 1 d . . .
O7 O 0.1792(9) 0.9974(8) 0.8003(6) 0.124(3) Uani 1 1 d . . .
O8 O 0.1525(8) 1.0362(7) 0.9393(5) 0.110(2) Uani 1 1 d . . .
N1 N 1.0182(7) 0.9208(6) 0.3532(4) 0.0541(17) Uani 1 1 d D . .
H1 H 0.958(7) 0.955(7) 0.383(5) 0.081 Uiso 1 1 d D . .
N2 N 1.0941(6) 0.7467(5) 0.3471(4) 0.0465(15) Uani 1 1 d D . .
H2 H 1.174(5) 0.774(7) 0.321(4) 0.070 Uiso 1 1 d D . .
N3 N 0.9239(7) 0.5343(6) 0.2332(4) 0.0540(16) Uani 1 1 d D . .
H3 H 0.859(7) 0.573(7) 0.246(5) 0.081 Uiso 1 1 d D . .
N4 N 0.8574(8) 0.5334(8) 0.0940(4) 0.079(2) Uani 1 1 d D . .
H4 H 0.884(11) 0.524(10) 0.039(3) 0.118 Uiso 1 1 d D . .
N5 N 0.4003(6) 1.1646(5) 0.6470(4) 0.0489(16) Uani 1 1 d D . .
H5 H 0.325(6) 1.189(7) 0.633(5) 0.073 Uiso 1 1 d D . .
N6 N 0.4850(6) 0.9972(5) 0.6496(4) 0.0503(16) Uani 1 1 d D . .
H6 H 0.557(6) 1.049(6) 0.688(4) 0.075 Uiso 1 1 d D . .
N7 N 0.3311(7) 0.8425(6) 0.7524(5) 0.0611(18) Uani 1 1 d D . .
H7 H 0.266(7) 0.877(8) 0.740(6) 0.092 Uiso 1 1 d D . .
N8 N 0.2790(9) 0.9118(8) 0.8903(5) 0.089(2) Uani 1 1 d D . .
H8 H 0.317(12) 0.936(10) 0.945(3) 0.133 Uiso 1 1 d D . .
C1 C 1.2016(10) 1.1648(8) 0.2501(6) 0.078(3) Uani 1 1 d . . .
H1A H 1.2977 1.1927 0.2766 0.117 Uiso 1 1 calc R . .
H1B H 1.1739 1.2383 0.2446 0.117 Uiso 1 1 calc R . .
H1C H 1.1973 1.1113 0.1929 0.117 Uiso 1 1 calc R . .
C2 C 1.1239(9) 0.9850(7) 0.3097(5) 0.052(2) Uani 1 1 d . . .
C3 C 0.9973(7) 0.8022(6) 0.3704(4) 0.0433(18) Uani 1 1 d . . .
C4 C 1.0834(7) 0.6237(6) 0.3613(4) 0.0446(18) Uani 1 1 d . . .
C5 C 1.1569(8) 0.6116(6) 0.4301(4) 0.0493(19) Uani 1 1 d . . .
H5A H 1.2138 0.6845 0.4692 0.059 Uiso 1 1 calc R . .
C6 C 1.1485(9) 0.4954(7) 0.4427(5) 0.062(2) Uani 1 1 d . . .
H6A H 1.2001 0.4877 0.4905 0.075 Uiso 1 1 calc R . .
C7 C 1.0659(9) 0.3891(7) 0.3869(6) 0.064(2) Uani 1 1 d . . .
H7A H 1.0584 0.3083 0.3970 0.076 Uiso 1 1 calc R . .
C8 C 0.9937(8) 0.4001(7) 0.3157(5) 0.059(2) Uani 1 1 d . . .
H8A H 0.9379 0.3268 0.2765 0.070 Uiso 1 1 calc R . .
C9 C 1.0031(7) 0.5184(6) 0.3017(4) 0.0463(18) Uani 1 1 d . . .
C10 C 0.9415(8) 0.5030(8) 0.1517(5) 0.064(2) Uani 1 1 d . . .
C11 C 0.7543(10) 0.5877(9) 0.1150(7) 0.076(3) Uani 1 1 d . . .
C12 C 0.5862(13) 0.6617(12) 0.0566(8) 0.122(4) Uani 1 1 d . . .
H12A H 0.4961 0.6012 0.0639 0.183 Uiso 1 1 calc R . .
H12B H 0.5765 0.6970 0.0065 0.183 Uiso 1 1 calc R . .
H12C H 0.6142 0.7295 0.1082 0.183 Uiso 1 1 calc R . .
C13 C 0.6113(9) 1.4730(7) 0.7442(6) 0.069(2) Uani 1 1 d . . .
H13A H 0.6601 1.4432 0.7849 0.103 Uiso 1 1 calc R . .
H13B H 0.5691 1.5340 0.7762 0.103 Uiso 1 1 calc R . .
H13C H 0.6786 1.5132 0.7062 0.103 Uiso 1 1 calc R . .
C14 C 0.5170(8) 1.2560(6) 0.6890(5) 0.0477(18) Uani 1 1 d . . .
C15 C 0.3779(7) 1.0350(6) 0.6266(4) 0.0481(19) Uani 1 1 d . . .
C16 C 0.4749(8) 0.8665(6) 0.6336(5) 0.050(2) Uani 1 1 d . . .
C17 C 0.5478(9) 0.8213(7) 0.5703(5) 0.066(2) Uani 1 1 d . . .
H17A H 0.6036 0.8762 0.5375 0.079 Uiso 1 1 calc R . .
C18 C 0.5420(10) 0.6946(8) 0.5527(6) 0.074(3) Uani 1 1 d . . .
H18A H 0.5908 0.6630 0.5070 0.089 Uiso 1 1 calc R . .
C19 C 0.4646(10) 0.6165(8) 0.6023(6) 0.071(2) Uani 1 1 d . . .
H19A H 0.4601 0.5304 0.5912 0.085 Uiso 1 1 calc R . .
C20 C 0.3933(9) 0.6636(7) 0.6688(6) 0.068(2) Uani 1 1 d . . .
H20A H 0.3394 0.6093 0.7026 0.081 Uiso 1 1 calc R . .
C21 C 0.4002(8) 0.7891(6) 0.6861(5) 0.052(2) Uani 1 1 d . . .
C22 C 0.3523(10) 0.8495(8) 0.8349(6) 0.075(2) Uani 1 1 d . . .
C23 C 0.2004(11) 0.9820(9) 0.8707(8) 0.086(3) Uani 1 1 d . . .
C24 C 0.0586(14) 1.1072(12) 0.9274(9) 0.130(5) Uani 1 1 d . . .
H24A H 0.0988 1.1641 0.8891 0.195 Uiso 1 1 calc R . .
H24B H 0.0464 1.1564 0.9833 0.195 Uiso 1 1 calc R . .
H24C H -0.0328 1.0492 0.9018 0.195 Uiso 1 1 calc R . .
O9A O 0.324(3) 0.950(3) 0.0606(13) 0.142(8) Uiso 0.52(3) 1 d P A 1
C25A C 0.336(3) 0.848(2) 0.0948(14) 0.101(10) Uiso 0.52(3) 1 d P A 1
O9B O 0.265(3) 0.888(2) 0.0685(11) 0.116(8) Uiso 0.48(3) 1 d P A 2
C25B C 0.243(3) 0.768(2) 0.0831(14) 0.096(10) Uiso 0.48(3) 1 d P A 2
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 O2 C1 115.3(6) . . ?
C11 O4 C12 114.9(8) . . ?
C14 O6 C13 115.9(6) . . ?
C23 O8 C24 118.0(9) . . ?
C2 N1 C3 127.4(6) . . ?
C2 N1 H1 124(6) . . ?
C3 N1 H1 108(6) . . ?
C3 N2 C4 122.2(6) . . ?
C3 N2 H2 130(5) . . ?
C4 N2 H2 108(5) . . ?
C10 N3 C9 125.7(6) . . ?
C10 N3 H3 116(5) . . ?
C9 N3 H3 118(5) . . ?
C11 N4 C10 126.2(7) . . ?
C11 N4 H4 119(7) . . ?
C10 N4 H4 115(7) . . ?
C14 N5 C15 127.2(6) . . ?
C14 N5 H5 118(5) . . ?
C15 N5 H5 115(5) . . ?
C15 N6 C16 121.4(6) . . ?
C15 N6 H6 122(5) . . ?
C16 N6 H6 115(5) . . ?
C22 N7 C21 126.3(7) . . ?
C22 N7 H7 114(6) . . ?
C21 N7 H7 120(6) . . ?
C23 N8 C22 127.2(9) . . ?
C23 N8 H8 114(7) . . ?
C22 N8 H8 113(8) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 126.1(8) . . ?
O1 C2 N1 124.3(7) . . ?
O2 C2 N1 109.6(7) . . ?
N2 C3 N1 117.2(6) . . ?
N2 C3 S1 123.4(5) . . ?
N1 C3 S1 119.4(5) . . ?
C5 C4 C9 120.9(6) . . ?
C5 C4 N2 120.2(6) . . ?
C9 C4 N2 118.8(6) . . ?
C6 C5 C4 120.1(6) . . ?
C6 C5 H5A 119.9 . . ?
C4 C5 H5A 119.9 . . ?
C5 C6 C7 120.5(7) . . ?
C5 C6 H6A 119.7 . . ?
C7 C6 H6A 119.7 . . ?
C6 C7 C8 119.8(7) . . ?
C6 C7 H7A 120.1 . . ?
C8 C7 H7A 120.1 . . ?
C7 C8 C9 120.0(7) . . ?
C7 C8 H8A 120.0 . . ?
C9 C8 H8A 120.0 . . ?
C8 C9 C4 118.5(6) . . ?
C8 C9 N3 122.0(6) . . ?
C4 C9 N3 119.3(6) . . ?
N3 C10 N4 116.9(7) . . ?
N3 C10 S2 125.5(6) . . ?
N4 C10 S2 117.6(6) . . ?
O3 C11 O4 125.0(9) . . ?
O3 C11 N4 125.9(8) . . ?
O4 C11 N4 109.1(9) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O6 C13 H13A 109.5 . . ?
O6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 O6 124.9(7) . . ?
O5 C14 N5 125.4(6) . . ?
O6 C14 N5 109.8(6) . . ?
N6 C15 N5 115.8(6) . . ?
N6 C15 S3 124.3(5) . . ?
N5 C15 S3 119.9(5) . . ?
C17 C16 C21 120.2(7) . . ?
C17 C16 N6 118.8(7) . . ?
C21 C16 N6 120.8(6) . . ?
C16 C17 C18 120.9(8) . . ?
C16 C17 H17A 119.6 . . ?
C18 C17 H17A 119.6 . . ?
C19 C18 C17 119.3(8) . . ?
C19 C18 H18A 120.4 . . ?
C17 C18 H18A 120.4 . . ?
C18 C19 C20 119.9(8) . . ?
C18 C19 H19A 120.1 . . ?
C20 C19 H19A 120.1 . . ?
C21 C20 C19 120.5(8) . . ?
C21 C20 H20A 119.7 . . ?
C19 C20 H20A 119.7 . . ?
C20 C21 C16 119.1(7) . . ?
C20 C21 N7 123.3(8) . . ?
C16 C21 N7 117.5(6) . . ?
N7 C22 N8 117.4(7) . . ?
N7 C22 S4 123.8(7) . . ?
N8 C22 S4 118.7(7) . . ?
O7 C23 O8 122.6(10) . . ?
O7 C23 N8 125.4(9) . . ?
O8 C23 N8 112.0(11) . . ?
O8 C24 H24A 109.5 . . ?
O8 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O8 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
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 1.666(7) . ?
S2 C10 1.671(8) . ?
S3 C15 1.654(7) . ?
S4 C22 1.674(9) . ?
O1 C2 1.197(9) . ?
O2 C2 1.325(9) . ?
O2 C1 1.464(10) . ?
O3 C11 1.184(10) . ?
O4 C11 1.330(10) . ?
O4 C12 1.471(11) . ?
O5 C14 1.218(8) . ?
O6 C14 1.316(8) . ?
O6 C13 1.450(9) . ?
O7 C23 1.197(12) . ?
O8 C23 1.309(12) . ?
O8 C24 1.451(12) . ?
N1 C2 1.371(10) . ?
N1 C3 1.391(9) . ?
N1 H1 0.90(2) . ?
N2 C3 1.328(8) . ?
N2 C4 1.441(8) . ?
N2 H2 0.90(2) . ?
N3 C10 1.300(9) . ?
N3 C9 1.417(9) . ?
N3 H3 0.90(2) . ?
N4 C11 1.368(11) . ?
N4 C10 1.404(10) . ?
N4 H4 0.92(2) . ?
N5 C14 1.367(9) . ?
N5 C15 1.397(8) . ?
N5 H5 0.92(2) . ?
N6 C15 1.347(8) . ?
N6 C16 1.434(8) . ?
N6 H6 0.91(2) . ?
N7 C22 1.310(10) . ?
N7 C21 1.403(10) . ?
N7 H7 0.90(2) . ?
N8 C23 1.358(13) . ?
N8 C22 1.376(11) . ?
N8 H8 0.90(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C4 C5 1.369(9) . ?
C4 C9 1.391(9) . ?
C5 C6 1.361(9) . ?
C5 H5A 0.9500 . ?
C6 C7 1.376(10) . ?
C6 H6A 0.9500 . ?
C7 C8 1.387(11) . ?
C7 H7A 0.9500 . ?
C8 C9 1.390(10) . ?
C8 H8A 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C16 C17 1.357(11) . ?
C16 C21 1.395(10) . ?
C17 C18 1.400(11) . ?
C17 H17A 0.9500 . ?
C18 C19 1.376(12) . ?
C18 H18A 0.9500 . ?
C19 C20 1.388(12) . ?
C19 H19A 0.9500 . ?
C20 C21 1.384(10) . ?
C20 H20A 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O9A C25A 1.41(3) . ?
O9B C25B 1.39(3) . ?
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 O1 0.90(2) 2.12(7) 2.671(7) 119(6) .
N3 H3 O3 0.90(2) 1.93(6) 2.665(8) 138(7) .
N3 H3 S1 0.90(2) 2.99(7) 3.568(6) 124(6) .
N6 H6 O5 0.91(2) 2.01(6) 2.660(7) 128(6) .
N7 H7 O7 0.90(2) 1.94(6) 2.671(8) 137(8) .
N7 H7 S3 0.90(2) 2.90(8) 3.482(7) 124(7) .
N1 H1 S3 0.90(2) 2.54(3) 3.410(6) 164(7) 2_676
N2 H2 O5 0.90(2) 2.20(4) 3.022(8) 152(7) 2_776
N4 H4 S2 0.92(2) 2.55(4) 3.429(8) 162(9) 2_765
N5 H5 S1 0.92(2) 2.41(2) 3.323(6) 173(7) 2_676
N6 H6 O1 0.91(2) 2.30(6) 3.006(8) 134(6) 2_776
N8 H8 O9A 0.90(2) 1.81(5) 2.67(2) 158(12) 1_556
N8 H8 O9B 0.90(2) 2.17(9) 2.90(2) 138(10) 1_556
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 O2 C2 O1 7.0(11) . . . . ?
C1 O2 C2 N1 -172.9(7) . . . . ?
C3 N1 C2 O1 -1.7(12) . . . . ?
C3 N1 C2 O2 178.1(6) . . . . ?
C4 N2 C3 N1 -179.7(6) . . . . ?
C4 N2 C3 S1 0.0(9) . . . . ?
C2 N1 C3 N2 4.4(10) . . . . ?
C2 N1 C3 S1 -175.4(6) . . . . ?
C3 N2 C4 C5 -99.4(8) . . . . ?
C3 N2 C4 C9 83.7(8) . . . . ?
C9 C4 C5 C6 -2.2(11) . . . . ?
N2 C4 C5 C6 -178.9(6) . . . . ?
C4 C5 C6 C7 -0.3(12) . . . . ?
C5 C6 C7 C8 1.9(12) . . . . ?
C6 C7 C8 C9 -1.0(12) . . . . ?
C7 C8 C9 C4 -1.3(11) . . . . ?
C7 C8 C9 N3 -175.7(7) . . . . ?
C5 C4 C9 C8 3.0(10) . . . . ?
N2 C4 C9 C8 179.8(6) . . . . ?
C5 C4 C9 N3 177.4(7) . . . . ?
N2 C4 C9 N3 -5.7(10) . . . . ?
C10 N3 C9 C8 -68.4(11) . . . . ?
C10 N3 C9 C4 117.3(8) . . . . ?
C9 N3 C10 N4 -176.3(7) . . . . ?
C9 N3 C10 S2 1.5(12) . . . . ?
C11 N4 C10 N3 -3.2(14) . . . . ?
C11 N4 C10 S2 178.8(8) . . . . ?
C12 O4 C11 O3 2.0(15) . . . . ?
C12 O4 C11 N4 -176.5(9) . . . . ?
C10 N4 C11 O3 3.9(17) . . . . ?
C10 N4 C11 O4 -177.6(8) . . . . ?
C13 O6 C14 O5 -6.4(10) . . . . ?
C13 O6 C14 N5 173.5(6) . . . . ?
C15 N5 C14 O5 -2.9(12) . . . . ?
C15 N5 C14 O6 177.2(6) . . . . ?
C16 N6 C15 N5 179.0(6) . . . . ?
C16 N6 C15 S3 -2.1(10) . . . . ?
C14 N5 C15 N6 -1.3(10) . . . . ?
C14 N5 C15 S3 179.7(6) . . . . ?
C15 N6 C16 C17 106.9(8) . . . . ?
C15 N6 C16 C21 -77.9(9) . . . . ?
C21 C16 C17 C18 4.3(12) . . . . ?
N6 C16 C17 C18 179.5(7) . . . . ?
C16 C17 C18 C19 -2.1(12) . . . . ?
C17 C18 C19 C20 0.2(13) . . . . ?
C18 C19 C20 C21 -0.6(12) . . . . ?
C19 C20 C21 C16 2.7(11) . . . . ?
C19 C20 C21 N7 -179.8(8) . . . . ?
C17 C16 C21 C20 -4.6(11) . . . . ?
N6 C16 C21 C20 -179.7(6) . . . . ?
C17 C16 C21 N7 177.7(7) . . . . ?
N6 C16 C21 N7 2.6(10) . . . . ?
C22 N7 C21 C20 61.7(11) . . . . ?
C22 N7 C21 C16 -120.8(9) . . . . ?
C21 N7 C22 N8 176.5(8) . . . . ?
C21 N7 C22 S4 -6.5(13) . . . . ?
C23 N8 C22 N7 -9.6(16) . . . . ?
C23 N8 C22 S4 173.3(9) . . . . ?
C24 O8 C23 O7 6.4(17) . . . . ?
C24 O8 C23 N8 -175.8(9) . . . . ?
C22 N8 C23 O7 2.5(19) . . . . ?
C22 N8 C23 O8 -175.3(10) . . . . ?
