#------------------------------------------------------------------------------
#$Date: 2022-06-14 11:55:37 +0300 (Tue, 14 Jun 2022) $
#$Revision: 276018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/54/8105407.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_8105407
loop_
_publ_author_name
'Ding, Qichun'
'Yang, Ruya'
'Yao, Peipao'
_publ_section_title
;
 Synthesis and crystal structure of
 ((6R,7S)-3-ethyl-6-phenyl-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)(phenyl)methanone
 hemihydrate, 2(C19H18N4OS) ⋅ H2O
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1157
_journal_page_last               1159
_journal_paper_doi               10.1515/ncrs-2020-0219
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         '2(C19 H18 N4 O S), H2 O'
_chemical_formula_sum            'C38 H38 N8 O3 S2'
_chemical_formula_weight         718.88
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_cell_angle_alpha                97.5790(10)
_cell_angle_beta                 97.9670(10)
_cell_angle_gamma                109.8350(10)
_cell_formula_units_Z            2
_cell_length_a                   10.1773(12)
_cell_length_b                   12.9096(15)
_cell_length_c                   15.1950(18)
_cell_measurement_reflns_used    5582
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.471
_cell_measurement_theta_min      2.220
_cell_volume                     1825.2(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14724
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.593
_diffrn_reflns_theta_min         2.561
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. 
wR2(int) was 0.0799 before and 0.0299 after correction.
The Ratio of minimum to maximum transmission is 0.9364. 
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     526
_refine_ls_number_reflns         7804
_refine_ls_number_restraints     184
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0609P)²+0.7748P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1412
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5694
_reflns_number_total             7804
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0219_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105407
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.949
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All S(H,H) groups
2. Restrained distances
 O3-H3a = O3-H3b
 0.85 with sigma of 0.01
 H3b-H3a
 1.39 with sigma of 0.01
 C36-C28
 2.1 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C19 \\sim C19A \\sim C18A \\sim C18 \\sim C17 \\sim C17A \\sim C38: within 2.8A
with sigma of 0.01 and sigma for terminal atoms of 0.02
C38 \\sim C38A \\sim C37A \\sim C37 \\sim C36A \\sim C36: within 2.8A with
sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C19A)=Sof(H19d)=Sof(H19e)=Sof(H19f)=Sof(C18A)=Sof(H18c)=Sof(H18d)=
 Sof(C17A)=1-FVAR(1)
 Sof(C17)=Sof(C18)=Sof(H18a)=Sof(H18b)=Sof(C19)=Sof(H19a)=Sof(H19b)=Sof(H19c)=
 FVAR(1)
 Sof(C37A)=Sof(H37c)=Sof(H37d)=Sof(C36A)=Sof(C38A)=Sof(H38d)=Sof(H38e)=
 Sof(H38f)=1-FVAR(2)
 Sof(C36)=Sof(C37)=Sof(H37a)=Sof(H37b)=Sof(C38)=Sof(H38a)=Sof(H38b)=Sof(H38c)=
 FVAR(2)
5.a Riding coordinates:
 N1(H1a), N5(H5a)
5.b Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C27(H27), C29(H29)
5.c Secondary CH2 refined with riding coordinates:
 C18(H18a,H18b), C37(H37a,H37b), C18A(H18c,H18d), C37A(H37c,H37d)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C31(H31),
  C32(H32), C33(H33), C34(H34), C35(H35)
5.e Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c), C38(H38a,H38b,H38c), C19A(H19d,H19e,H19f), C38A(H38d,
 H38e,H38f)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.2435(3) 0.2258(2) 0.9373(2) 0.0665(7) Uani 1 1 d . . . . .
H1 H -0.339489 0.192598 0.938996 0.080 Uiso 1 1 calc R . . . .
C2 C -0.1549(3) 0.3106(2) 1.00634(19) 0.0676(7) Uani 1 1 d . . . . .
H2 H -0.191441 0.335658 1.054121 0.081 Uiso 1 1 calc R . . . .
C3 C -0.0120(2) 0.3588(2) 1.00537(16) 0.0533(5) Uani 1 1 d . . . . .
H3 H 0.047521 0.416116 1.052626 0.064 Uiso 1 1 calc R . . . .
C4 C 0.0440(2) 0.32222(16) 0.93393(13) 0.0368(4) Uani 1 1 d . . . . .
C5 C -0.0475(2) 0.23829(18) 0.86343(15) 0.0490(5) Uani 1 1 d . . . . .
H5 H -0.012637 0.214271 0.814380 0.059 Uiso 1 1 calc R . . . .
C6 C -0.1914(2) 0.1899(2) 0.86581(19) 0.0643(7) Uani 1 1 d . . . . .
H6 H -0.252187 0.132966 0.818714 0.077 Uiso 1 1 calc R . . . .
C7 C 0.1999(2) 0.37287(17) 0.93830(13) 0.0399(4) Uani 1 1 d . . . . .
C8 C 0.2619(2) 0.33793(17) 0.85840(13) 0.0385(4) Uani 1 1 d . . . . .
H8 H 0.199154 0.262700 0.825893 0.046 Uiso 1 1 calc R . . . .
C9 C 0.41296(19) 0.33767(17) 0.88998(12) 0.0382(4) Uani 1 1 d . . . . .
H9 H 0.474927 0.412686 0.923401 0.046 Uiso 1 1 calc R . . . .
C10 C 0.3950(2) 0.43431(18) 0.72978(14) 0.0465(5) Uani 1 1 d . . . . .
C11 C 0.4091(2) 0.25366(17) 0.95106(13) 0.0393(4) Uani 1 1 d . . . . .
C12 C 0.4857(2) 0.2899(2) 1.03908(14) 0.0497(5) Uani 1 1 d . . . . .
H12 H 0.535094 0.366160 1.061248 0.060 Uiso 1 1 calc R . . . .
C13 C 0.4894(3) 0.2135(3) 1.09441(16) 0.0632(7) Uani 1 1 d . . . . .
H13 H 0.541287 0.238725 1.153462 0.076 Uiso 1 1 calc R . . . .
C14 C 0.4173(3) 0.1010(3) 1.06281(19) 0.0686(7) Uani 1 1 d . . . . .
H14 H 0.420563 0.050093 1.100204 0.082 Uiso 1 1 calc R . . . .
C15 C 0.3401(3) 0.0636(2) 0.97592(19) 0.0657(7) Uani 1 1 d . . . . .
H15 H 0.290676 -0.012788 0.954391 0.079 Uiso 1 1 calc R . . . .
C16 C 0.3360(2) 0.13975(19) 0.92018(16) 0.0517(5) Uani 1 1 d . . . . .
H16 H 0.283352 0.113951 0.861328 0.062 Uiso 1 1 calc R . . . .
C17 C 0.5726(6) 0.4007(5) 0.6927(4) 0.0484(11) Uani 0.736(10) 1 d . U P A 2
C18 C 0.6935(6) 0.3590(5) 0.6944(3) 0.0581(12) Uani 0.736(10) 1 d . U P A 2
H18A H 0.719246 0.354843 0.635306 0.070 Uiso 0.736(10) 1 calc R . P A 2
H18B H 0.663786 0.284152 0.708127 0.070 Uiso 0.736(10) 1 calc R . P A 2
C19 C 0.8220(6) 0.4366(5) 0.7651(4) 0.0811(16) Uani 0.736(10) 1 d . U P A 2
H19A H 0.852070 0.510479 0.751161 0.122 Uiso 0.736(10) 1 calc GR . P A 2
H19B H 0.898245 0.408706 0.765190 0.122 Uiso 0.736(10) 1 calc GR . P A 2
H19C H 0.796913 0.439715 0.823798 0.122 Uiso 0.736(10) 1 calc GR . P A 2
C20 C 0.8375(4) 0.2481(4) 0.2969(2) 0.0949(11) Uani 1 1 d . . . . .
H20 H 0.926093 0.280100 0.281815 0.114 Uiso 1 1 calc R . . . .
C21 C 0.7734(4) 0.1352(4) 0.2817(2) 0.0941(10) Uani 1 1 d . . . . .
H21 H 0.818727 0.090035 0.257143 0.113 Uiso 1 1 calc R . . . .
C22 C 0.6428(3) 0.0872(3) 0.30232(18) 0.0702(7) Uani 1 1 d . . . . .
H22 H 0.598814 0.009483 0.290514 0.084 Uiso 1 1 calc R . . . .
C23 C 0.5744(2) 0.1532(2) 0.34080(14) 0.0488(5) Uani 1 1 d . . . . .
C24 C 0.6415(3) 0.2680(2) 0.35689(18) 0.0647(7) Uani 1 1 d . . . . .
H24 H 0.598044 0.313589 0.383163 0.078 Uiso 1 1 calc R . . . .
C25 C 0.7727(3) 0.3162(3) 0.3344(2) 0.0862(9) Uani 1 1 d . . . . .
H25 H 0.816930 0.393876 0.344563 0.103 Uiso 1 1 calc R . . . .
C26 C 0.4335(2) 0.0953(2) 0.36268(14) 0.0508(5) Uani 1 1 d . . . . .
C27 C 0.3657(2) 0.1605(2) 0.42094(14) 0.0503(5) Uani 1 1 d . . . . .
H27 H 0.412383 0.241078 0.423269 0.060 Uiso 1 1 calc R . . . .
C28 C 0.2638(3) 0.15025(19) 0.57725(14) 0.0538(6) Uani 1 1 d D . . . .
C29 C 0.2044(2) 0.12390(19) 0.38401(13) 0.0452(5) Uani 1 1 d . . . . .
H29 H 0.159639 0.043799 0.384522 0.054 Uiso 1 1 calc R . . . .
C30 C 0.1746(2) 0.14087(18) 0.28733(13) 0.0424(5) Uani 1 1 d . . . . .
C31 C 0.0824(2) 0.0515(2) 0.22193(14) 0.0493(5) Uani 1 1 d . . . . .
H31 H 0.040891 -0.017918 0.237548 0.059 Uiso 1 1 calc R . . . .
C32 C 0.0513(3) 0.0641(2) 0.13373(15) 0.0618(6) Uani 1 1 d . . . . .
H32 H -0.010366 0.003147 0.090067 0.074 Uiso 1 1 calc R . . . .
C33 C 0.1111(3) 0.1664(2) 0.11017(16) 0.0678(7) Uani 1 1 d . . . . .
H33 H 0.089641 0.174963 0.050678 0.081 Uiso 1 1 calc R . . . .
C34 C 0.2024(3) 0.2558(2) 0.17429(17) 0.0684(7) Uani 1 1 d . . . . .
H34 H 0.242929 0.325147 0.158317 0.082 Uiso 1 1 calc R . . . .
C35 C 0.2348(3) 0.2435(2) 0.26293(16) 0.0583(6) Uani 1 1 d . . . . .
H35 H 0.297230 0.304485 0.306211 0.070 Uiso 1 1 calc R . . . .
C36 C 0.071(4) 0.173(5) 0.584(4) 0.059(3) Uani 0.31(3) 1 d D U P B 1
C37 C -0.081(3) 0.165(2) 0.5537(17) 0.066(3) Uani 0.31(3) 1 d . U P B 2
H37A H -0.117199 0.122350 0.492406 0.079 Uiso 0.31(3) 1 calc R . P B 2
H37B H -0.144575 0.131099 0.592483 0.079 Uiso 0.31(3) 1 calc R . P B 2
C38 C -0.066(2) 0.276(3) 0.5568(13) 0.085(4) Uani 0.31(3) 1 d . U P B 2
H38A H -0.158166 0.282092 0.547986 0.128 Uiso 0.31(3) 1 calc GR . P B 2
H38B H -0.017750 0.304026 0.509802 0.128 Uiso 0.31(3) 1 calc GR . P B 2
H38C H -0.011063 0.320064 0.614619 0.128 Uiso 0.31(3) 1 calc GR . P B 2
N1 N 0.47500(18) 0.30655(15) 0.81389(11) 0.0452(4) Uani 1 1 d . . . . .
H1A H 0.433705 0.237276 0.787735 0.054 Uiso 1 1 d R . . . .
N2 N 0.48464(18) 0.38140(15) 0.75320(12) 0.0463(4) Uani 1 1 d . . . . .
N3 N 0.4321(2) 0.48750(18) 0.66437(14) 0.0652(6) Uani 1 1 d . . . . .
N4 N 0.5512(3) 0.4667(2) 0.64418(16) 0.0778(7) Uani 1 1 d . . . . .
N5 N 0.13590(19) 0.18472(17) 0.43789(11) 0.0503(4) Uani 1 1 d . . . . .
H5A H 0.159604 0.254007 0.433001 0.060 Uiso 1 1 d R . . . .
N6 N 0.1548(2) 0.17005(16) 0.52867(11) 0.0506(4) Uani 1 1 d . . . . .
N7 N 0.2415(3) 0.14128(17) 0.65939(12) 0.0637(6) Uani 1 1 d . . . . .
N8 N 0.1137(3) 0.15671(18) 0.66420(13) 0.0678(6) Uani 1 1 d . . . . .
O1 O 0.27862(16) 0.44176(14) 1.00343(11) 0.0603(4) Uani 1 1 d . . . . .
O2 O 0.3700(2) -0.00529(16) 0.33684(13) 0.0739(5) Uani 1 1 d . . . . .
O3 O 0.2769(2) 0.42970(19) 0.47432(13) 0.0894(7) Uani 1 1 d D . . . .
S1 S 0.25895(6) 0.44010(5) 0.78554(4) 0.05375(17) Uani 1 1 d . . . . .
S2 S 0.40207(9) 0.12811(8) 0.53420(4) 0.0805(3) Uani 1 1 d . . . . .
H3A H 0.336(3) 0.462(3) 0.4430(17) 0.121 Uiso 1 1 d DR . . . .
H3B H 0.316(3) 0.449(3) 0.5300(8) 0.121 Uiso 1 1 d DR . . . .
C19A C 0.8665(12) 0.4765(11) 0.7243(10) 0.070(3) Uani 0.264(10) 1 d . U P A 1
H19D H 0.859901 0.493776 0.664642 0.105 Uiso 0.264(10) 1 calc GR . P A 1
H19E H 0.945594 0.452612 0.737092 0.105 Uiso 0.264(10) 1 calc GR . P A 1
H19F H 0.880434 0.542120 0.767907 0.105 Uiso 0.264(10) 1 calc GR . P A 1
C18A C 0.7313(17) 0.3842(14) 0.7292(12) 0.059(3) Uani 0.264(10) 1 d . U P A 1
H18C H 0.715983 0.318970 0.683557 0.071 Uiso 0.264(10) 1 calc R . P A 1
H18D H 0.741316 0.363075 0.788029 0.071 Uiso 0.264(10) 1 calc R . P A 1
C17A C 0.6121(18) 0.4161(17) 0.7158(12) 0.054(3) Uani 0.264(10) 1 d . U P A 1
C37A C -0.0682(11) 0.2028(12) 0.5590(7) 0.0684(19) Uani 0.69(3) 1 d . U P B 1
H37C H -0.120915 0.159370 0.499755 0.082 Uiso 0.69(3) 1 calc R . P B 1
H37D H -0.128754 0.180783 0.602444 0.082 Uiso 0.69(3) 1 calc R . P B 1
C36A C 0.0589(16) 0.172(2) 0.5857(14) 0.0579(15) Uani 0.69(3) 1 d . U P B 2
C38A C -0.0358(12) 0.3264(13) 0.5578(5) 0.075(2) Uani 0.69(3) 1 d . U P B 1
H38D H 0.009155 0.369616 0.617488 0.113 Uiso 0.69(3) 1 calc GR . P B 1
H38E H -0.122829 0.337892 0.538674 0.113 Uiso 0.69(3) 1 calc GR . P B 1
H38F H 0.026914 0.349673 0.516507 0.113 Uiso 0.69(3) 1 calc GR . P B 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'
N N 0.0061 0.0033 '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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 H1 119.9 . .
C6 C1 H1 119.9 . .
C6 C1 C2 120.3(2) . .
C1 C2 H2 119.8 . .
C1 C2 C3 120.3(2) . .
C3 C2 H2 119.8 . .
C2 C3 H3 119.8 . .
C2 C3 C4 120.4(2) . .
C4 C3 H3 119.8 . .
C3 C4 C7 118.31(19) . .
C5 C4 C3 118.64(19) . .
C5 C4 C7 123.03(18) . .
C4 C5 H5 119.9 . .
C4 C5 C6 120.2(2) . .
C6 C5 H5 119.9 . .
C1 C6 C5 120.1(2) . .
C1 C6 H6 119.9 . .
C5 C6 H6 119.9 . .
C4 C7 C8 118.96(17) . .
O1 C7 C4 121.56(18) . .
O1 C7 C8 119.48(18) . .
C7 C8 H8 109.3 . .
C7 C8 C9 111.60(16) . .
C7 C8 S1 104.02(13) . .
C9 C8 H8 109.3 . .
C9 C8 S1 113.15(12) . .
S1 C8 H8 109.3 . .
C8 C9 H9 109.0 . .
C11 C9 C8 110.75(15) . .
C11 C9 H9 109.0 . .
N1 C9 C8 112.19(15) . .
N1 C9 H9 109.0 . .
N1 C9 C11 106.75(16) . .
N2 C10 S1 124.33(15) . .
N3 C10 N2 110.48(19) . .
N3 C10 S1 124.99(18) . .
C12 C11 C9 119.73(19) . .
C12 C11 C16 118.45(19) . .
C16 C11 C9 121.75(18) . .
C11 C12 H12 119.8 . .
C11 C12 C13 120.5(2) . .
C13 C12 H12 119.8 . .
C12 C13 H13 119.8 . .
C14 C13 C12 120.5(2) . .
C14 C13 H13 119.8 . .
C13 C14 H14 120.0 . .
C13 C14 C15 119.9(2) . .
C15 C14 H14 120.0 . .
C14 C15 H15 120.0 . .
C14 C15 C16 119.9(2) . .
C16 C15 H15 120.0 . .
C11 C16 C15 120.8(2) . .
C11 C16 H16 119.6 . .
C15 C16 H16 119.6 . .
N2 C17 C18 122.3(5) . .
N4 C17 C18 124.8(4) . .
N4 C17 N2 112.4(5) . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
C17 C18 C19 110.7(4) . .
H18A C18 H18B 108.1 . .
C19 C18 H18A 109.5 . .
C19 C18 H18B 109.5 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19B 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C21 C20 H20 119.7 . .
C21 C20 C25 120.6(3) . .
C25 C20 H20 119.7 . .
C20 C21 H21 119.8 . .
C20 C21 C22 120.3(3) . .
C22 C21 H21 119.8 . .
C21 C22 H22 119.6 . .
C21 C22 C23 120.7(3) . .
C23 C22 H22 119.6 . .
C22 C23 C26 117.8(2) . .
C24 C23 C22 118.4(2) . .
C24 C23 C26 123.9(2) . .
C23 C24 H24 119.7 . .
C23 C24 C25 120.7(3) . .
C25 C24 H24 119.7 . .
C20 C25 C24 119.3(3) . .
C20 C25 H25 120.3 . .
C24 C25 H25 120.3 . .
C23 C26 C27 120.4(2) . .
O2 C26 C23 121.5(2) . .
O2 C26 C27 118.1(2) . .
C26 C27 H27 109.8 . .
C26 C27 C29 111.46(18) . .
C26 C27 S2 104.17(15) . .
C29 C27 H27 109.8 . .
C29 C27 S2 111.77(15) . .
S2 C27 H27 109.8 . .
N6 C28 S2 124.92(16) . .
N7 C28 N6 109.9(2) . .
N7 C28 S2 125.0(2) . .
C27 C29 H29 108.2 . .
C30 C29 C27 111.52(17) . .
C30 C29 H29 108.2 . .
N5 C29 C27 113.01(17) . .
N5 C29 H29 108.2 . .
N5 C29 C30 107.48(16) . .
C31 C30 C29 118.99(19) . .
C31 C30 C35 118.84(19) . .
C35 C30 C29 122.2(2) . .
C30 C31 H31 119.7 . .
C32 C31 C30 120.6(2) . .
C32 C31 H31 119.7 . .
C31 C32 H32 119.9 . .
C33 C32 C31 120.1(2) . .
C33 C32 H32 119.9 . .
C32 C33 H33 120.1 . .
C34 C33 C32 119.9(2) . .
C34 C33 H33 120.1 . .
C33 C34 H34 119.9 . .
C33 C34 C35 120.2(2) . .
C35 C34 H34 119.9 . .
C30 C35 C34 120.3(2) . .
C30 C35 H35 119.9 . .
C34 C35 H35 119.9 . .
N6 C36 N8 114.4(14) . .
N6 C36 C37A 122(4) . .
N8 C36 C37A 123(2) . .
H37A C37 H37B 109.1 . .
C38 C37 H37A 111.1 . .
C38 C37 H37B 111.1 . .
C38 C37 C36A 103.3(18) . .
C36A C37 H37A 111.1 . .
C36A C37 H37B 111.1 . .
C37 C38 H38A 109.5 . .
C37 C38 H38B 109.5 . .
C37 C38 H38C 109.5 . .
H38A C38 H38B 109.5 . .
H38A C38 H38C 109.5 . .
H38B C38 H38C 109.5 . .
C9 N1 H1A 113.3 . .
N2 N1 C9 111.01(15) . .
N2 N1 H1A 113.2 . .
C10 N2 C17 103.4(3) . .
C10 N2 N1 128.74(16) . .
C10 N2 C17A 113.4(8) . .
C17 N2 N1 126.9(3) . .
N1 N2 C17A 117.6(8) . .
C10 N3 N4 106.16(19) . .
C17 N4 N3 107.2(3) . .
N3 N4 C17A 111.6(8) . .
C29 N5 H5A 113.3 . .
N6 N5 C29 111.02(16) . .
N6 N5 H5A 113.1 . .
C28 N6 N5 128.59(18) . .
C28 N6 C36A 106.7(8) . .
C36 N6 C28 104.4(18) . .
C36 N6 N5 127.0(18) . .
C36A N6 N5 124.7(8) . .
C28 N7 N8 106.6(2) . .
C36 N8 N7 104.6(7) . .
C36A N8 N7 109.8(4) . .
H3A O3 H3B 109.6(16) . .
C10 S1 C8 99.42(9) . .
C28 S2 C27 99.48(10) . .
H19D C19A H19E 109.5 . .
H19D C19A H19F 109.5 . .
H19E C19A H19F 109.5 . .
C18A C19A H19D 109.5 . .
C18A C19A H19E 109.5 . .
C18A C19A H19F 109.5 . .
C19A C18A H18C 109.1 . .
C19A C18A H18D 109.1 . .
H18C C18A H18D 107.9 . .
C17A C18A C19A 112.3(13) . .
C17A C18A H18C 109.1 . .
C17A C18A H18D 109.1 . .
N2 C17A N4 94.6(10) . .
C18A C17A N2 129.3(13) . .
C18A C17A N4 134.1(14) . .
C36 C37A H37C 108.8 . .
C36 C37A H37D 108.8 . .
H37C C37A H37D 107.7 . .
C38A C37A C36 114(2) . .
C38A C37A H37C 108.8 . .
C38A C37A H37D 108.8 . .
N6 C36A C37 122.8(19) . .
N8 C36A C37 128.9(14) . .
N8 C36A N6 106.9(8) . .
C37A C38A H38D 109.5 . .
C37A C38A H38E 109.5 . .
C37A C38A H38F 109.5 . .
H38D C38A H38E 109.5 . .
H38D C38A H38F 109.5 . .
H38E C38A H38F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1 0.9300 .
C1 C2 1.370(4) .
C1 C6 1.367(4) .
C2 H2 0.9300 .
C2 C3 1.377(3) .
C3 H3 0.9300 .
C3 C4 1.395(3) .
C4 C5 1.386(3) .
C4 C7 1.484(3) .
C5 H5 0.9300 .
C5 C6 1.391(3) .
C6 H6 0.9300 .
C7 C8 1.529(3) .
C7 O1 1.215(2) .
C8 H8 0.9800 .
C8 C9 1.547(3) .
C8 S1 1.8357(19) .
C9 H9 0.9800 .
C9 C11 1.512(3) .
C9 N1 1.466(2) .
C10 N2 1.350(3) .
C10 N3 1.308(3) .
C10 S1 1.738(2) .
C11 C12 1.383(3) .
C11 C16 1.384(3) .
C12 H12 0.9300 .
C12 C13 1.385(3) .
C13 H13 0.9300 .
C13 C14 1.368(4) .
C14 H14 0.9300 .
C14 C15 1.371(4) .
C15 H15 0.9300 .
C15 C16 1.387(3) .
C16 H16 0.9300 .
C17 C18 1.500(7) .
C17 N2 1.359(6) .
C17 N4 1.250(7) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C18 C19 1.518(7) .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 H20 0.9300 .
C20 C21 1.352(5) .
C20 C25 1.378(5) .
C21 H21 0.9300 .
C21 C22 1.363(4) .
C22 H22 0.9300 .
C22 C23 1.392(3) .
C23 C24 1.376(3) .
C23 C26 1.482(3) .
C24 H24 0.9300 .
C24 C25 1.380(4) .
C25 H25 0.9300 .
C26 C27 1.529(3) .
C26 O2 1.218(3) .
C27 H27 0.9800 .
C27 C29 1.543(3) .
C27 S2 1.842(2) .
C28 N6 1.363(3) .
C28 N7 1.312(3) .
C28 S2 1.723(3) .
C29 H29 0.9800 .
C29 C30 1.518(3) .
C29 N5 1.460(3) .
C30 C31 1.380(3) .
C30 C35 1.382(3) .
C31 H31 0.9300 .
C31 C32 1.378(3) .
C32 H32 0.9300 .
C32 C33 1.372(4) .
C33 H33 0.9300 .
C33 C34 1.367(4) .
C34 H34 0.9300 .
C34 C35 1.385(3) .
C35 H35 0.9300 .
C36 N6 1.29(3) .
C36 N8 1.30(5) .
C36 C37A 1.60(2) .
C37 H37A 0.9700 .
C37 H37B 0.9700 .
C37 C38 1.38(2) .
C37 C36A 1.41(3) .
C38 H38A 0.9600 .
C38 H38B 0.9600 .
C38 H38C 0.9600 .
N1 H1A 0.8597 .
N1 N2 1.410(2) .
N2 C17A 1.444(18) .
N3 N4 1.391(3) .
N4 C17A 1.507(17) .
N5 H5A 0.8602 .
N5 N6 1.413(2) .
N6 C36A 1.395(12) .
N7 N8 1.392(3) .
N8 C36A 1.31(2) .
O3 H3A 0.850(10) .
O3 H3B 0.849(10) .
C19A H19D 0.9600 .
C19A H19E 0.9600 .
C19A H19F 0.9600 .
C19A C18A 1.503(19) .
C18A H18C 0.9700 .
C18A H18D 0.9700 .
C18A C17A 1.41(2) .
C37A H37C 0.9700 .
C37A H37D 0.9700 .
C37A C38A 1.518(8) .
C38A H38D 0.9600 .
C38A H38E 0.9600 .
C38A H38F 0.9600 .
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
_geom_hbond_publ_flag
O3 H3A N4 0.850(10) 1.987(10) 2.831(3) 171(3) 2_666 yes
O3 H3B N3 0.849(10) 2.115(11) 2.960(3) 173(4) . yes
O3 H3B N4 0.849(10) 2.67(2) 3.385(4) 142(3) . yes
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
C1 C2 C3 C4 0.2(4) . . . .
C2 C1 C6 C5 0.8(4) . . . .
C2 C3 C4 C5 1.3(3) . . . .
C2 C3 C4 C7 -177.0(2) . . . .
C3 C4 C5 C6 -1.8(3) . . . .
C3 C4 C7 C8 -177.00(18) . . . .
C3 C4 C7 O1 2.5(3) . . . .
C4 C5 C6 C1 0.8(4) . . . .
C4 C7 C8 C9 -146.54(17) . . . .
C4 C7 C8 S1 91.13(18) . . . .
C5 C4 C7 C8 4.8(3) . . . .
C5 C4 C7 O1 -175.7(2) . . . .
C6 C1 C2 C3 -1.3(4) . . . .
C7 C4 C5 C6 176.4(2) . . . .
C7 C8 C9 C11 62.0(2) . . . .
C7 C8 C9 N1 -178.83(16) . . . .
C7 C8 S1 C10 154.99(13) . . . .
C8 C9 C11 C12 -119.4(2) . . . .
C8 C9 C11 C16 63.7(2) . . . .
C8 C9 N1 N2 59.2(2) . . . .
C9 C8 S1 C10 33.69(16) . . . .
C9 C11 C12 C13 -176.59(19) . . . .
C9 C11 C16 C15 176.5(2) . . . .
C9 N1 N2 C10 -34.8(3) . . . .
C9 N1 N2 C17 158.2(3) . . . .
C9 N1 N2 C17A 139.0(9) . . . .
C10 N2 C17A N4 -18.0(12) . . . .
C10 N2 C17A C18A 176.3(15) . . . .
C10 N3 N4 C17 3.4(4) . . . .
C10 N3 N4 C17A -13.0(8) . . . .
C11 C9 N1 N2 -179.32(16) . . . .
C11 C12 C13 C14 0.0(4) . . . .
C12 C11 C16 C15 -0.5(3) . . . .
C12 C13 C14 C15 -0.3(4) . . . .
C13 C14 C15 C16 0.3(4) . . . .
C14 C15 C16 C11 0.1(4) . . . .
C16 C11 C12 C13 0.4(3) . . . .
C18 C17 N2 C10 178.5(4) . . . .
C18 C17 N2 N1 -11.9(6) . . . .
C18 C17 N4 N3 -178.1(4) . . . .
C20 C21 C22 C23 -1.3(5) . . . .
C21 C20 C25 C24 0.2(5) . . . .
C21 C22 C23 C24 0.5(4) . . . .
C21 C22 C23 C26 -179.1(3) . . . .
C22 C23 C24 C25 0.7(4) . . . .
C22 C23 C26 C27 168.3(2) . . . .
C22 C23 C26 O2 -10.1(3) . . . .
C23 C24 C25 C20 -1.0(5) . . . .
C23 C26 C27 C29 138.7(2) . . . .
C23 C26 C27 S2 -100.6(2) . . . .
C24 C23 C26 C27 -11.2(3) . . . .
C24 C23 C26 O2 170.4(2) . . . .
C25 C20 C21 C22 0.9(6) . . . .
C26 C23 C24 C25 -179.8(2) . . . .
C26 C27 C29 C30 -58.6(2) . . . .
C26 C27 C29 N5 -179.84(17) . . . .
C26 C27 S2 C28 -155.04(16) . . . .
C27 C29 C30 C31 126.3(2) . . . .
C27 C29 C30 C35 -55.0(3) . . . .
C27 C29 N5 N6 -58.5(2) . . . .
C28 N6 C36A C37 -166(2) . . . .
C28 N6 C36A N8 1.8(19) . . . .
C28 N7 N8 C36 0(3) . . . .
C28 N7 N8 C36A 1.6(13) . . . .
C29 C27 S2 C28 -34.57(18) . . . .
C29 C30 C31 C32 179.1(2) . . . .
C29 C30 C35 C34 -178.7(2) . . . .
C29 N5 N6 C28 28.6(3) . . . .
C29 N5 N6 C36 -151(4) . . . .
C29 N5 N6 C36A -150.2(14) . . . .
C30 C29 N5 N6 178.06(17) . . . .
C30 C31 C32 C33 -0.5(4) . . . .
C31 C30 C35 C34 0.1(3) . . . .
C31 C32 C33 C34 0.4(4) . . . .
C32 C33 C34 C35 0.0(4) . . . .
C33 C34 C35 C30 -0.3(4) . . . .
C35 C30 C31 C32 0.3(3) . . . .
C38 C37 C36A N6 -89(3) . . . .
C38 C37 C36A N8 106(3) . . . .
N1 C9 C11 C12 118.2(2) . . . .
N1 C9 C11 C16 -58.7(2) . . . .
N1 N2 C17A N4 167.2(5) . . . .
N1 N2 C17A C18A 2(2) . . . .
N2 C10 N3 N4 0.6(3) . . . .
N2 C10 S1 C8 -10.2(2) . . . .
N2 C17 C18 C19 -81.1(6) . . . .
N2 C17 N4 N3 -6.2(5) . . . .
N3 C10 N2 C17 -4.0(3) . . . .
N3 C10 N2 N1 -173.3(2) . . . .
N3 C10 N2 C17A 12.7(9) . . . .
N3 C10 S1 C8 175.5(2) . . . .
N3 N4 C17A N2 18.2(12) . . . .
N3 N4 C17A C18A -177.3(17) . . . .
N4 C17 C18 C19 90.1(6) . . . .
N4 C17 N2 C10 6.4(5) . . . .
N4 C17 N2 N1 176.0(3) . . . .
N5 C29 C30 C31 -109.3(2) . . . .
N5 C29 C30 C35 69.4(3) . . . .
N5 N6 C36A C37 13(3) . . . .
N5 N6 C36A N8 -179.2(8) . . . .
N6 C28 N7 N8 -0.4(3) . . . .
N6 C28 S2 C27 7.9(2) . . . .
N6 C36 N8 N7 0(5) . . . .
N6 C36 C37A C38A -74(5) . . . .
N7 C28 N6 C36 0(3) . . . .
N7 C28 N6 N5 -179.8(2) . . . .
N7 C28 N6 C36A -0.8(12) . . . .
N7 C28 S2 C27 -178.1(2) . . . .
N7 N8 C36A C37 164(2) . . . .
N7 N8 C36A N6 -2(2) . . . .
N8 C36 N6 C28 0(5) . . . .
N8 C36 N6 N5 -180(2) . . . .
N8 C36 C37A C38A 101(5) . . . .
O1 C7 C8 C9 34.0(3) . . . .
O1 C7 C8 S1 -88.4(2) . . . .
O2 C26 C27 C29 -42.8(3) . . . .
O2 C26 C27 S2 77.8(2) . . . .
S1 C8 C9 C11 178.92(14) . . . .
S1 C8 C9 N1 -61.9(2) . . . .
S1 C10 N2 C17 -179.0(3) . . . .
S1 C10 N2 N1 11.7(3) . . . .
S1 C10 N2 C17A -162.3(8) . . . .
S1 C10 N3 N4 175.54(19) . . . .
S2 C27 C29 C30 -174.75(15) . . . .
S2 C27 C29 N5 64.0(2) . . . .
S2 C28 N6 C36 175(3) . . . .
S2 C28 N6 N5 -5.0(3) . . . .
S2 C28 N6 C36A 174.0(12) . . . .
S2 C28 N7 N8 -175.21(18) . . . .
C19A C18A C17A N2 -148.4(18) . . . .
C19A C18A C17A N4 52(2) . . . .
C37A C36 N6 C28 175(4) . . . .
C37A C36 N6 N5 -5(7) . . . .
C37A C36 N8 N7 -176(4) . . . .
