#------------------------------------------------------------------------------
#$Date: 2022-05-11 11:22:13 +0300 (Wed, 11 May 2022) $
#$Revision: 275330 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/52/8105217.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_8105217
loop_
_publ_author_name
'Yu, Xiang'
'Chen, Ya-Fang'
'Huang, Guo-Juan'
'Zhang, You-Fang'
'Yang, Wu-De'
_publ_section_title
;
 Synthesis and crystal structure of
 4-(3-acetyl-5-(thiophen-2-yl)-2,3-dihydro-1,3,4-oxadiazol-2-yl)-7-(diethylamino)-2H-chromen-2-one,
 C21H21N3O4S
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              561
_journal_page_last               562
_journal_paper_doi               10.1515/ncrs-2019-0807
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C21 H21 N3 O4 S'
_chemical_formula_sum            'C21 H21 N3 O4 S'
_chemical_formula_weight         411.47
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                101.896(7)
_cell_angle_beta                 104.770(8)
_cell_angle_gamma                93.271(8)
_cell_formula_units_Z            2
_cell_length_a                   9.4256(9)
_cell_length_b                   10.1906(9)
_cell_length_c                   11.6539(9)
_cell_measurement_reflns_used    2770
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9670
_cell_measurement_theta_min      4.4410
_cell_volume                     1052.02(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9769
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   21.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000  -30.0000 42

#__ type_ start__ end____ width___ exp.time_
  2 omega   20.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000 -150.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega    6.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000 -180.0000 61

#__ type_ start__ end____ width___ exp.time_
  4 omega   51.00  132.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -150.0000 81

#__ type_ start__ end____ width___ exp.time_
  5 omega   84.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
  6 omega   77.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -30.0000 39

#__ type_ start__ end____ width___ exp.time_
  7 omega   57.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 46

#__ type_ start__ end____ width___ exp.time_
  8 omega   56.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 41

#__ type_ start__ end____ width___ exp.time_
  9 omega   55.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 37

#__ type_ start__ end____ width___ exp.time_
 10 omega   47.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 36

#__ type_ start__ end____ width___ exp.time_
 11 omega   41.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 41

#__ type_ start__ end____ width___ exp.time_
 12 omega   39.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 47

#__ type_ start__ end____ width___ exp.time_
 13 omega   76.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000    0.0000 51

#__ type_ start__ end____ width___ exp.time_
 14 omega   94.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 82

#__ type_ start__ end____ width___ exp.time_
 15 omega   69.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000  -90.0000 37

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 52

#__ type_ start__ end____ width___ exp.time_
 17 omega   54.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
 18 omega   92.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -180.0000 85

#__ type_ start__ end____ width___ exp.time_
 19 omega   65.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 43

#__ type_ start__ end____ width___ exp.time_
 20 omega   45.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 49

#__ type_ start__ end____ width___ exp.time_
 21 omega   41.00   66.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 22 omega   11.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000  -30.0000 47

#__ type_ start__ end____ width___ exp.time_
 23 omega   12.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   19.0000 -120.0000 96

#__ type_ start__ end____ width___ exp.time_
 24 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000   90.0000 94

#__ type_ start__ end____ width___ exp.time_
 25 omega   59.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 26 omega  -11.00   16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 27 omega  -28.00    9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000  -30.0000 37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1089117000
_diffrn_orient_matrix_UB_12      0.1296710000
_diffrn_orient_matrix_UB_13      0.0350791000
_diffrn_orient_matrix_UB_21      -0.0983587000
_diffrn_orient_matrix_UB_22      0.0742085000
_diffrn_orient_matrix_UB_23      0.0730249000
_diffrn_orient_matrix_UB_31      0.0862530000
_diffrn_orient_matrix_UB_32      -0.0433145000
_diffrn_orient_matrix_UB_33      0.1147266000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6696
_diffrn_reflns_theta_full        71.03
_diffrn_reflns_theta_max         71.03
_diffrn_reflns_theta_min         4.46
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.636
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3974
_refine_ls_number_restraints     81
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0469
_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)+(0.0729P)²+0.0838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1354
_reflns_number_gt                3247
_reflns_number_total             3974
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2019-0807_suppl.cif
_cod_data_source_block           exp_6162
_cod_original_cell_volume        1052.01(16)
_cod_database_code               8105217
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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 0.3209(2) 0.86736(10) 0.54845(15) 0.0699(4) Uani 0.765(3) 1 d PU A 1
O3 O 0.35405(12) 1.64767(12) 0.93678(11) 0.0465(3) Uani 1 1 d . . .
O1 O 0.49362(13) 1.25150(11) 0.67409(11) 0.0477(3) Uani 1 1 d . . .
C6 C 0.52568(16) 1.54452(15) 0.83358(14) 0.0354(3) Uani 1 1 d . . .
C5 C 0.49654(16) 1.63830(16) 0.92865(14) 0.0375(3) Uani 1 1 d . . .
C2 C 0.40280(17) 1.46273(15) 0.74320(14) 0.0368(3) Uani 1 1 d . . .
C4 C 0.23475(18) 1.56782(19) 0.85243(17) 0.0463(4) Uani 1 1 d . . .
C10 C 0.60394(18) 1.72762(17) 1.01599(15) 0.0436(4) Uani 1 1 d . . .
H10 H 0.5783 1.7885 1.0765 0.052 Uiso 1 1 calc R . .
N2 N 0.30037(17) 1.30349(14) 0.53937(14) 0.0483(4) Uani 1 1 d . . .
C7 C 0.67543(17) 1.54263(16) 0.83497(15) 0.0407(4) Uani 1 1 d . . .
H7 H 0.7004 1.4807 0.7747 0.049 Uiso 1 1 calc R . .
C9 C 0.75276(18) 1.72769(18) 1.01458(15) 0.0432(4) Uani 1 1 d . . .
C3 C 0.26431(18) 1.47354(18) 0.75289(16) 0.0453(4) Uani 1 1 d . . .
H3 H 0.1858 1.4189 0.6940 0.054 Uiso 1 1 calc R . .
C8 C 0.78497(17) 1.62892(18) 0.92206(16) 0.0443(4) Uani 1 1 d . . .
H8 H 0.8827 1.6230 0.9209 0.053 Uiso 1 1 calc R . .
O4 O 0.11499(14) 1.58523(16) 0.86756(14) 0.0648(4) Uani 1 1 d . . .
O2 O 0.27241(19) 1.48231(15) 0.45825(14) 0.0722(4) Uani 1 1 d . . .
C1 C 0.43234(18) 1.36717(16) 0.63566(15) 0.0413(4) Uani 1 1 d . . .
H1 H 0.5005 1.4136 0.6021 0.050 Uiso 1 1 calc R . .
N3 N 0.86110(17) 1.81957(18) 1.09744(16) 0.0586(4) Uani 1 1 d . . .
N1 N 0.28204(18) 1.16358(15) 0.52977(14) 0.0516(4) Uani 1 1 d . . .
C19 C 0.5419(11) 0.9900(11) 0.7199(10) 0.076(3) Uani 0.765(3) 1 d PDU A 1
H19 H 0.6118 1.0574 0.7745 0.092 Uiso 0.765(3) 1 calc PR A 1
C17 C 0.39545(19) 1.14207(17) 0.60778(16) 0.0441(4) Uani 1 1 d . A .
C15 C 0.2308(2) 1.3645(2) 0.45148(18) 0.0563(5) Uani 1 1 d . . .
C18 C 0.4296(2) 1.01254(18) 0.63274(18) 0.0509(4) Uani 1 1 d DU . .
C21 C 0.4278(4) 0.7755(2) 0.6294(3) 0.0810(7) Uani 1 1 d DU . .
H21 H 0.4092 0.6820 0.6130 0.097 Uiso 0.765(3) 1 calc PR A 1
H21A H 0.3974 0.6833 0.6054 0.097 Uiso 0.235(3) 1 calc PR A 2
C16 C 0.1037(3) 1.2825(3) 0.3536(2) 0.0835(8) Uani 1 1 d . . .
H16A H 0.1360 1.2017 0.3145 0.125 Uiso 1 1 calc R . .
H16B H 0.0665 1.3342 0.2945 0.125 Uiso 1 1 calc R . .
H16C H 0.0269 1.2589 0.3887 0.125 Uiso 1 1 calc R . .
C13 C 0.8266(2) 1.9275(2) 1.18590(19) 0.0634(5) Uani 1 1 d . . .
H13A H 0.9145 1.9597 1.2532 0.076 Uiso 1 1 calc R . .
H13B H 0.7517 1.8909 1.2181 0.076 Uiso 1 1 calc R . .
C20 C 0.5414(3) 0.8439(3) 0.7188(3) 0.0794(7) Uani 1 1 d DU A .
H20 H 0.6095 0.8064 0.7720 0.095 Uiso 0.765(3) 1 calc PR A 1
H20A H 0.6025 0.7967 0.7678 0.095 Uiso 0.235(3) 1 calc PR A 2
C11 C 1.0159(2) 1.8213(2) 1.0982(2) 0.0730(7) Uani 1 1 d . . .
H11A H 1.0628 1.9137 1.1263 0.088 Uiso 1 1 calc R . .
H11B H 1.0221 1.7881 1.0157 0.088 Uiso 1 1 calc R . .
C14 C 0.7726(3) 2.0446(3) 1.1348(3) 0.0891(8) Uani 1 1 d . . .
H14A H 0.8484 2.0850 1.1072 0.134 Uiso 1 1 calc R . .
H14B H 0.7488 2.1102 1.1970 0.134 Uiso 1 1 calc R . .
H14C H 0.6860 2.0137 1.0676 0.134 Uiso 1 1 calc R . .
C12 C 1.0963(3) 1.7386(4) 1.1769(4) 0.1264(15) Uani 1 1 d . . .
H12A H 1.0960 1.7746 1.2597 0.190 Uiso 1 1 calc R . .
H12B H 1.1963 1.7397 1.1715 0.190 Uiso 1 1 calc R . .
H12C H 1.0489 1.6474 1.1507 0.190 Uiso 1 1 calc R . .
S2 S 0.5752(10) 0.9964(8) 0.7440(9) 0.0658(12) Uani 0.235(3) 1 d PU A 2
C22 C 0.363(2) 0.8880(9) 0.5784(17) 0.068(3) Uani 0.235(3) 1 d PDU A 2
H22 H 0.2797 0.8722 0.5119 0.082 Uiso 0.235(3) 1 calc PR 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
C21 S1 C18 91.06(13) . .
C4 O3 C5 122.15(13) . .
C17 O1 C1 106.00(13) . .
C5 C6 C2 118.05(14) . .
C5 C6 C7 115.87(14) . .
C7 C6 C2 126.05(14) . .
O3 C5 C6 120.68(14) . .
C10 C5 O3 115.95(14) . .
C10 C5 C6 123.35(14) . .
C6 C2 C1 118.47(13) . .
C3 C2 C6 120.26(15) . .
C3 C2 C1 121.25(15) . .
O3 C4 C3 117.20(14) . .
O4 C4 O3 116.68(17) . .
O4 C4 C3 126.10(18) . .
C5 C10 H10 119.8 . .
C5 C10 C9 120.36(15) . .
C9 C10 H10 119.8 . .
N1 N2 C1 110.86(13) . .
C15 N2 C1 123.07(15) . .
C15 N2 N1 123.75(16) . .
C6 C7 H7 119.0 . .
C8 C7 C6 121.99(15) . .
C8 C7 H7 119.0 . .
C10 C9 C8 116.96(15) . .
N3 C9 C10 121.49(15) . .
N3 C9 C8 121.55(15) . .
C2 C3 C4 121.61(16) . .
C2 C3 H3 119.2 . .
C4 C3 H3 119.2 . .
C7 C8 C9 121.37(14) . .
C7 C8 H8 119.3 . .
C9 C8 H8 119.3 . .
O1 C1 C2 109.63(13) . .
O1 C1 N2 101.61(12) . .
O1 C1 H1 110.2 . .
C2 C1 H1 110.2 . .
N2 C1 C2 114.66(14) . .
N2 C1 H1 110.2 . .
C9 N3 C13 121.50(15) . .
C9 N3 C11 122.52(16) . .
C11 N3 C13 115.86(16) . .
C17 N1 N2 104.32(14) . .
C18 C19 H19 124.2 . .
C18 C19 C20 111.6(7) . .
C20 C19 H19 124.2 . .
O1 C17 C18 116.81(16) . .
N1 C17 O1 117.04(15) . .
N1 C17 C18 126.15(17) . .
N2 C15 C16 116.84(18) . .
O2 C15 N2 118.84(18) . .
O2 C15 C16 124.29(19) . .
C19 C18 S1 112.5(5) . .
C19 C18 C17 126.6(5) . .
C19 C18 S2 4.2(7) . .
C19 C18 C22 102.3(9) . .
C17 C18 S1 120.83(15) . .
C17 C18 S2 122.4(3) . .
S2 C18 S1 116.7(3) . .
C22 C18 S1 10.3(5) . .
C22 C18 C17 131.0(5) . .
C22 C18 S2 106.5(3) . .
S1 C21 H21 122.0 . .
S1 C21 H21A 114.2 . .
H21 C21 H21A 7.8 . .
C20 C21 S1 115.99(19) . .
C20 C21 H21 122.0 . .
C20 C21 H21A 129.8 . .
C20 C21 C22 100.5(4) . .
C22 C21 S1 15.6(4) . .
C22 C21 H21 137.5 . .
C22 C21 H21A 129.8 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16B 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
N3 C13 H13A 108.8 . .
N3 C13 H13B 108.8 . .
N3 C13 C14 113.9(2) . .
H13A C13 H13B 107.7 . .
C14 C13 H13A 108.8 . .
C14 C13 H13B 108.8 . .
C19 C20 H20 125.6 . .
C19 C20 H20A 132.3 . .
C19 C20 S2 13.6(5) . .
C21 C20 C19 108.8(4) . .
C21 C20 H20 125.6 . .
C21 C20 H20A 118.8 . .
C21 C20 S2 122.4(4) . .
H20 C20 H20A 6.8 . .
S2 C20 H20 112.0 . .
S2 C20 H20A 118.8 . .
N3 C11 H11A 109.1 . .
N3 C11 H11B 109.1 . .
N3 C11 C12 112.6(2) . .
H11A C11 H11B 107.8 . .
C12 C11 H11A 109.1 . .
C12 C11 H11B 109.1 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C20 S2 C18 93.8(5) . .
C18 C22 C21 116.8(7) . .
C18 C22 H22 121.6 . .
C21 C22 H22 121.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C18 1.708(2) .
S1 C21 1.664(3) .
O3 C5 1.3776(18) .
O3 C4 1.377(2) .
O1 C1 1.4447(19) .
O1 C17 1.364(2) .
C6 C5 1.402(2) .
C6 C2 1.432(2) .
C6 C7 1.409(2) .
C5 C10 1.370(2) .
C2 C3 1.347(2) .
C2 C1 1.517(2) .
C4 C3 1.443(3) .
C4 O4 1.203(2) .
C10 H10 0.9300 .
C10 C9 1.407(2) .
N2 C1 1.457(2) .
N2 N1 1.404(2) .
N2 C15 1.354(2) .
C7 H7 0.9300 .
C7 C8 1.365(2) .
C9 C8 1.422(2) .
C9 N3 1.366(2) .
C3 H3 0.9300 .
C8 H8 0.9300 .
O2 C15 1.222(2) .
C1 H1 0.9800 .
N3 C13 1.457(2) .
N3 C11 1.456(2) .
N1 C17 1.277(2) .
C19 H19 0.9300 .
C19 C18 1.334(8) .
C19 C20 1.487(11) .
C17 C18 1.446(2) .
C15 C16 1.494(3) .
C18 S2 1.673(8) .
C18 C22 1.335(8) .
C21 H21 0.9300 .
C21 H21A 0.9300 .
C21 C20 1.328(4) .
C21 C22 1.489(11) .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C13 C14 1.499(4) .
C20 H20 0.9300 .
C20 H20A 0.9300 .
C20 S2 1.520(9) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 C12 1.471(4) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C22 H22 0.9300 .
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
S1 C18 S2 C20 -0.7(7) . . . .
S1 C18 C22 C21 -174(8) . . . .
S1 C21 C20 C19 -0.9(6) . . . .
S1 C21 C20 S2 -1.7(6) . . . .
S1 C21 C22 C18 176(6) . . . .
O3 C5 C10 C9 -179.01(15) . . . .
O3 C4 C3 C2 0.7(2) . . . .
O1 C17 C18 S1 -175.71(15) . . . .
O1 C17 C18 C19 5.0(8) . . . .
O1 C17 C18 S2 4.3(5) . . . .
O1 C17 C18 C22 -174.5(15) . . . .
C6 C5 C10 C9 -0.8(3) . . . .
C6 C2 C3 C4 0.8(2) . . . .
C6 C2 C1 O1 75.41(16) . . . .
C6 C2 C1 N2 -171.08(13) . . . .
C6 C7 C8 C9 -1.5(3) . . . .
C5 O3 C4 C3 -0.7(2) . . . .
C5 O3 C4 O4 -179.29(15) . . . .
C5 C6 C2 C3 -2.2(2) . . . .
C5 C6 C2 C1 176.21(13) . . . .
C5 C6 C7 C8 -1.4(2) . . . .
C5 C10 C9 C8 -2.1(3) . . . .
C5 C10 C9 N3 177.10(16) . . . .
C2 C6 C5 O3 2.3(2) . . . .
C2 C6 C5 C10 -175.86(15) . . . .
C2 C6 C7 C8 176.89(15) . . . .
C4 O3 C5 C6 -0.8(2) . . . .
C4 O3 C5 C10 177.44(14) . . . .
C10 C9 C8 C7 3.3(3) . . . .
C10 C9 N3 C13 -4.2(3) . . . .
C10 C9 N3 C11 179.7(2) . . . .
N2 N1 C17 O1 0.7(2) . . . .
N2 N1 C17 C18 -179.47(16) . . . .
C7 C6 C5 O3 -179.31(14) . . . .
C7 C6 C5 C10 2.6(2) . . . .
C7 C6 C2 C3 179.50(15) . . . .
C7 C6 C2 C1 -2.0(2) . . . .
C9 N3 C13 C14 -79.4(3) . . . .
C9 N3 C11 C12 -91.0(3) . . . .
C3 C2 C1 O1 -106.15(17) . . . .
C3 C2 C1 N2 7.4(2) . . . .
C8 C9 N3 C13 174.95(19) . . . .
C8 C9 N3 C11 -1.1(3) . . . .
O4 C4 C3 C2 179.15(18) . . . .
C1 O1 C17 N1 1.9(2) . . . .
C1 O1 C17 C18 -177.94(14) . . . .
C1 C2 C3 C4 -177.62(14) . . . .
C1 N2 N1 C17 -3.06(19) . . . .
C1 N2 C15 O2 -6.3(3) . . . .
C1 N2 C15 C16 175.46(19) . . . .
N3 C9 C8 C7 -175.96(17) . . . .
N1 N2 C1 O1 4.04(18) . . . .
N1 N2 C1 C2 -114.11(15) . . . .
N1 N2 C15 O2 -167.36(19) . . . .
N1 N2 C15 C16 14.4(3) . . . .
N1 C17 C18 S1 4.4(3) . . . .
N1 C17 C18 C19 -174.8(8) . . . .
N1 C17 C18 S2 -175.5(5) . . . .
N1 C17 C18 C22 5.6(16) . . . .
C19 C18 S2 C20 7(13) . . . .
C19 C18 C22 C21 1(2) . . . .
C19 C20 S2 C18 -2(4) . . . .
C17 O1 C1 C2 118.28(14) . . . .
C17 O1 C1 N2 -3.42(16) . . . .
C17 C18 S2 C20 179.3(3) . . . .
C17 C18 C22 C21 -179.4(8) . . . .
C15 N2 C1 O1 -159.20(17) . . . .
C15 N2 C1 C2 82.7(2) . . . .
C15 N2 N1 C17 160.04(18) . . . .
C18 S1 C21 C20 0.9(2) . . . .
C18 S1 C21 C22 -3(4) . . . .
C18 C19 C20 C21 0.4(11) . . . .
C18 C19 C20 S2 177(5) . . . .
C21 S1 C18 C19 -0.6(7) . . . .
C21 S1 C18 C17 -179.99(17) . . . .
C21 S1 C18 S2 0.0(5) . . . .
C21 S1 C18 C22 5(7) . . . .
C21 C20 S2 C18 1.4(8) . . . .
C13 N3 C11 C12 92.7(3) . . . .
C20 C19 C18 S1 0.3(11) . . . .
C20 C19 C18 C17 179.6(4) . . . .
C20 C19 C18 S2 -172(15) . . . .
C20 C19 C18 C22 -0.8(15) . . . .
C20 C21 C22 C18 -1(2) . . . .
C11 N3 C13 C14 97.0(2) . . . .
S2 C18 C22 C21 2(2) . . . .
C22 C18 S2 C20 -1.6(14) . . . .
C22 C21 C20 C19 0.2(12) . . . .
C22 C21 C20 S2 -0.7(12) . . . .
