#------------------------------------------------------------------------------
#$Date: 2020-07-04 04:57:57 +0300 (Sat, 04 Jul 2020) $
#$Revision: 253747 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/84/4038478.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_4038478
loop_
_publ_author_name
'Zheng, Nian'
'Liu, Ce'
'Ding, Ya-Nan'
'Shi, Wei-Yu'
'Zhang, Bo-Sheng'
'Liang, Yong-Min'
_publ_section_title
;
 Copper-Catalyzed Three-Component Redox-Neutral Ring Opening of
 Benzothiazoles to 1-Amino-N-(2-(phenylthio)phenyl)methanimine.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7666
_journal_page_last               7673
_journal_paper_doi               10.1021/acs.joc.9b03489
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C21 H24 N2 O2 S'
_chemical_formula_sum            'C21 H24 N2 O2 S'
_chemical_formula_weight         368.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-12-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.349(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.7949(5)
_cell_length_b                   11.2697(3)
_cell_length_c                   10.0677(3)
_cell_measurement_reflns_used    3181
_cell_measurement_temperature    293.1(2)
_cell_measurement_theta_max      69.5210
_cell_measurement_theta_min      5.7640
_cell_volume                     1956.02(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.1(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -71.00  -40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
  2 omega  -73.00  -46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -29.00    4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   57.0000    0.0000 33

#__ type_ start__ end____ width___ exp.time_
  4 omega   16.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   57.0000    0.0000 41

#__ type_ start__ end____ width___ exp.time_
  5 omega  -20.00    7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega  -14.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
  7 omega   24.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  120.0000 49

#__ type_ start__ end____ width___ exp.time_
  8 omega  -15.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
  9 omega   78.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega   64.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000    0.0000 38

#__ type_ start__ end____ width___ exp.time_
 11 omega   58.00  110.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
 12 omega   53.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   35.00   77.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 14 omega   81.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   57.00   84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 16 omega  100.00  170.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 70

#__ type_ start__ end____ width___ exp.time_
 17 omega   39.00   87.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 48

#__ type_ start__ end____ width___ exp.time_
 18 omega   36.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   60.0000 57

#__ type_ start__ end____ width___ exp.time_
 19 omega   66.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
 20 omega   85.00  143.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
 21 omega  141.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000 -150.0000 35

#__ type_ start__ end____ width___ exp.time_
 22 omega   54.00   94.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
 23 omega  -52.00  -26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega   87.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   34.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   90.0000 40

#__ type_ start__ end____ width___ exp.time_
 26 omega   41.00   84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 43

#__ type_ start__ end____ width___ exp.time_
 27 omega  146.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
 28 omega   40.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 29 omega   96.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
 30 omega   74.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000 -150.0000 28
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0703050000
_diffrn_orient_matrix_UB_12      0.0838378000
_diffrn_orient_matrix_UB_13      0.0414358000
_diffrn_orient_matrix_UB_21      0.0551226000
_diffrn_orient_matrix_UB_22      -0.1073440000
_diffrn_orient_matrix_UB_23      0.0152455000
_diffrn_orient_matrix_UB_31      0.0017376000
_diffrn_orient_matrix_UB_32      0.0121129000
_diffrn_orient_matrix_UB_33      -0.1515905000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8739
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        66.577
_diffrn_reflns_theta_max         66.577
_diffrn_reflns_theta_min         4.688
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         3345
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0686
_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)+(0.1414P)²+0.3041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1982
_refine_ls_wR_factor_ref         0.2127
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2760
_reflns_number_total             3345
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03489_si_004.cif
_cod_data_source_block           zhenn_1015
_cod_depositor_comments
'Adding full bibliography for 4038476--4038478.cif.'
_cod_original_cell_volume        1956.03(10)
_cod_database_code               4038478
_shelx_shelxl_version_number     2018/3
_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   0.831
_shelx_estimated_absorpt_t_min   0.751
_reflns_odcompleteness_completeness 96.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C8AA) \\sim Ueq, Uanis(C7AA) \\sim Ueq, Uanis(C6AA) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: H6A(0.5) H6B(0.5) N7(0.5) O11(0.5) C12(0.5) H12(0.5) C13(0.5)
 H13A(0.5) H13B(0.5) C14(0.5) H14A(0.5) H14B(0.5) O15(0.5) C18(0.5) C19(0.5)
 C20(0.5) H20A(0.5) H20B(0.5) C21(0.5) H21A(0.5) H21B(0.5) C22(0.5) H22A(0.5)
 H22B(0.5) C23(0.5) C24(0.5) H24(0.5) C25(0.5) H25(0.5) C26(0.5) H26A(0.5)
 H26B(0.5) C27(0.5) H27(0.5) C28(0.5) H28(0.5) C1(0.5) H1A(0.5) H1B(0.5)
 C0AA(0.5) H0AA(0.5) H0AB(0.5) C1AA(0.5) N3AA(0.5) O2AA(0.5) C4AA(0.5)
 H4AA(0.5) H4AB(0.5) C5AA(0.5) C8AA(0.5) H8AA(0.5) C7AA(0.5) H7AA(0.5)
 C9AA(0.5) C6AA(0.5) H6AA(0.5) O0BA(0.5) C1BA(0.5) H1BA(0.5) H1BB(0.5)
 C2AA(0.5) H2AA(0.5) H2AB(0.5) H2AC(0.5) C0BA(0.5) H0BA(0.5) H0BB(0.5)
 H0BC(0.5) H3AC(0.5) H3AD(0.5) H3AA(0.5) H3AB(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,
 H22B), C26(H26A,H26B), C1(H1A,H1B), C0AA(H0AA,H0AB), C4AA(H4AA,H4AB),
 C1BA(H1BA,H1BB), C3AA(H3AC,H3AD), C3AA(H3AA,H3AB)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6A), C6(H6B), C8(H8), C9(H9), C12(H12), C16(H16), C24(H24),
 C25(H25), C27(H27), C28(H28), C8AA(H8AA), C7AA(H7AA), C6AA(H6AA)
4.c Idealised Me refined as rotating group:
 C2AA(H2AA,H2AB,H2AC), C0BA(H0BA,H0BB,H0BC)
;
_olex2_date_sample_data_collection 2019-10-16
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
S1 S 0.22171(4) 0.01339(7) 0.35397(8) 0.0779(3) Uani 1 1 d . . . . .
N2 N 0.27482(12) -0.2179(2) 0.4275(3) 0.0762(6) Uani 1 1 d . . . . .
C3 C 0.20939(14) -0.1941(2) 0.4772(3) 0.0662(6) Uani 1 1 d . . . . .
C4 C 0.17790(13) -0.0791(2) 0.4545(2) 0.0599(6) Uani 1 1 d . . . . .
C5 C 0.1168(2) -0.2395(3) 0.6097(3) 0.0866(8) Uani 1 1 d . . . . .
H5 H 0.095783 -0.293459 0.660455 0.104 Uiso 1 1 calc R . . . .
C6 C 0.28065(15) -0.3205(3) 0.3758(3) 0.0779(8) Uani 1 1 d . . . . .
H6A H 0.244832 -0.380059 0.378127 0.093 Uiso 0.5 1 calc R . P A 1
H6B H 0.235512 -0.365177 0.348624 0.093 Uiso 0.5 1 calc R . P B 2
N7 N 0.3449(7) -0.3406(9) 0.3137(11) 0.070(2) Uani 0.5 1 d . . P C 1
C8 C 0.17824(18) -0.2725(3) 0.5561(3) 0.0793(8) Uani 1 1 d . . . . .
H8 H 0.199024 -0.348347 0.573067 0.095 Uiso 1 1 calc R . . . .
C9 C 0.11765(14) -0.0462(3) 0.5113(3) 0.0672(6) Uani 1 1 d . . . . .
H9 H 0.097731 0.030401 0.498004 0.081 Uiso 1 1 calc R . . . .
O11 O 0.5586(3) -0.5006(6) 0.3521(7) 0.0770(15) Uani 0.5 1 d . . P C 2
C12 C 0.2193(6) 0.2413(7) 0.4473(9) 0.078(2) Uani 0.5 1 d . . P D 1
H12 H 0.265801 0.221656 0.509072 0.094 Uiso 0.5 1 calc R . P D 1
C13 C 0.5722(16) -0.399(2) 0.162(3) 0.090(4) Uani 0.5 1 d . . P C 2
H13A H 0.589314 -0.316845 0.164887 0.108 Uiso 0.5 1 calc R . P C 2
H13B H 0.584142 -0.438615 0.084402 0.108 Uiso 0.5 1 calc R . P C 2
C14 C 0.4194(3) -0.5156(4) 0.2898(6) 0.0634(12) Uani 0.5 1 d . . P C 2
H14A H 0.407547 -0.552097 0.199737 0.076 Uiso 0.5 1 calc R . P C 2
H14B H 0.437984 -0.579216 0.354579 0.076 Uiso 0.5 1 calc R . P C 2
O15 O 0.4920(7) -0.4075(12) 0.1596(9) 0.092(2) Uani 0.5 1 d . . P C 2
C16 C 0.08677(16) -0.1265(3) 0.5877(3) 0.0780(8) Uani 1 1 d . . . . .
H16 H 0.045752 -0.103967 0.624183 0.094 Uiso 1 1 calc R . . . .
C18 C 0.1784(7) 0.1610(12) 0.3556(14) 0.064(3) Uani 0.5 1 d . . P D 1
C19 C 0.4892(5) -0.4384(7) 0.2949(9) 0.0565(15) Uani 0.5 1 d . . P C 2
C20 C 0.3917(3) -0.4836(5) 0.1943(7) 0.0755(15) Uani 0.5 1 d . . P C 1
H20A H 0.375163 -0.490691 0.095308 0.091 Uiso 0.5 1 calc R . P C 1
H20B H 0.401181 -0.563264 0.231019 0.091 Uiso 0.5 1 calc R . P C 1
C21 C 0.4827(3) -0.3271(5) 0.3787(6) 0.0642(11) Uani 0.5 1 d . . P C 2
H21A H 0.517529 -0.336889 0.468791 0.077 Uiso 0.5 1 calc R . P C 2
H21B H 0.501776 -0.260535 0.335478 0.077 Uiso 0.5 1 calc R . P C 2
C22 C 0.4533(4) -0.2933(5) 0.2801(9) 0.0805(16) Uani 0.5 1 d . . P C 1
H22A H 0.498484 -0.276744 0.354184 0.097 Uiso 0.5 1 calc R . P C 1
H22B H 0.456884 -0.240226 0.206026 0.097 Uiso 0.5 1 calc R . P C 1
C23 C 0.1075(5) 0.1870(6) 0.2654(8) 0.0645(17) Uani 0.5 1 d . . P D 1
C24 C 0.1207(9) 0.3889(7) 0.3602(15) 0.107(3) Uani 0.5 1 d . . P D 1
H24 H 0.101837 0.465652 0.362392 0.128 Uiso 0.5 1 calc R . P D 1
C25 C 0.0892(7) 0.1215(18) 0.2156(15) 0.120(6) Uani 0.5 1 d . . P D 2
H25 H 0.081192 0.049124 0.169816 0.143 Uiso 0.5 1 calc R . P D 2
C26 C 0.4059(4) -0.2615(5) 0.3150(10) 0.0785(17) Uani 0.5 1 d . . P C 1
H26A H 0.384599 -0.193297 0.259555 0.094 Uiso 0.5 1 calc R . P C 1
H26B H 0.425490 -0.233569 0.408317 0.094 Uiso 0.5 1 calc R . P C 1
C27 C 0.0823(6) 0.3109(13) 0.2750(12) 0.088(3) Uani 0.5 1 d . . P D 1
H27 H 0.035845 0.334575 0.215978 0.106 Uiso 0.5 1 calc R . P D 1
C28 C 0.1863(5) 0.3570(6) 0.4426(8) 0.098(2) Uani 0.5 1 d . . P D 1
H28 H 0.213606 0.413820 0.502519 0.118 Uiso 0.5 1 calc R . P D 1
C1 C 0.3545(4) -0.4862(5) 0.3094(9) 0.0722(15) Uani 0.5 1 d . . P C 2
H1A H 0.342451 -0.541988 0.374525 0.087 Uiso 0.5 1 calc R . P C 2
H1B H 0.315913 -0.497539 0.223516 0.087 Uiso 0.5 1 calc R . P C 2
C0AA C 0.3436(3) -0.4466(6) 0.2298(7) 0.0704(14) Uani 0.5 1 d . . P C 1
H0AA H 0.325846 -0.510228 0.279360 0.085 Uiso 0.5 1 calc R . P C 1
H0AB H 0.302400 -0.433478 0.147769 0.085 Uiso 0.5 1 calc R . P C 1
C1AA C 0.4676(4) -0.4179(6) 0.2290(13) 0.0651(15) Uani 0.5 1 d . . P C 1
N3AA N 0.3435(7) -0.3668(9) 0.3584(10) 0.065(2) Uani 0.5 1 d . . P C 2
O2AA O 0.5260(4) -0.4809(6) 0.3259(6) 0.0716(15) Uani 0.5 1 d . . P C 1
C4AA C 0.4176(4) -0.2990(6) 0.3952(9) 0.0771(16) Uani 0.5 1 d . . P C 2
H4AA H 0.405691 -0.223035 0.349496 0.093 Uiso 0.5 1 calc R . P C 2
H4AB H 0.426315 -0.282647 0.492488 0.093 Uiso 0.5 1 calc R . P C 2
C5AA C 0.1725(8) 0.2350(11) 0.3965(16) 0.114(3) Uani 0.5 1 d . . P D 2
C8AA C 0.0357(7) 0.2076(17) 0.1714(14) 0.156(4) Uani 0.5 1 d . U P D 2
H8AA H -0.010067 0.198142 0.103676 0.188 Uiso 0.5 1 calc R . P D 2
C7AA C 0.0558(9) 0.2960(14) 0.2314(15) 0.104(4) Uani 0.5 1 d . U P D 2
H7AA H 0.021679 0.357319 0.196184 0.125 Uiso 0.5 1 calc R . P D 2
C9AA C 0.1561(7) 0.1319(12) 0.3249(14) 0.074(3) Uani 0.5 1 d . . P D 2
C6AA C 0.1148(11) 0.3370(15) 0.339(2) 0.130(5) Uani 0.5 1 d . U P D 2
H6AA H 0.119210 0.414470 0.371594 0.156 Uiso 0.5 1 calc R . P D 2
O0BA O 0.4949(7) -0.4105(12) 0.1094(8) 0.093(2) Uani 0.5 1 d . . P C 1
C1BA C 0.5746(15) -0.425(2) 0.141(3) 0.090(5) Uani 0.5 1 d . . P C 1
H1BA H 0.598661 -0.350937 0.123531 0.109 Uiso 0.5 1 calc R . P C 1
H1BB H 0.587919 -0.485370 0.082254 0.109 Uiso 0.5 1 calc R . P C 1
C2AA C 0.2359(11) 0.252(2) 0.507(2) 0.255(15) Uani 0.5 1 d . . P D 2
H2AA H 0.236951 0.190135 0.573458 0.382 Uiso 0.5 1 calc GR . P D 2
H2AB H 0.231833 0.327475 0.548092 0.382 Uiso 0.5 1 calc GR . P D 2
H2AC H 0.282723 0.248793 0.476069 0.382 Uiso 0.5 1 calc GR . P D 2
C0BA C 0.0605(6) 0.0944(14) 0.1704(13) 0.096(3) Uani 0.5 1 d . . P D 1
H0BA H 0.090652 0.063738 0.111166 0.143 Uiso 0.5 1 calc GR . P D 1
H0BB H 0.013973 0.130083 0.116186 0.143 Uiso 0.5 1 calc GR . P D 1
H0BC H 0.047213 0.030889 0.223900 0.143 Uiso 0.5 1 calc GR . P D 1
C3AA C 0.6053(2) -0.4597(4) 0.2890(5) 0.1020(11) Uani 1 1 d . . . . .
H3AC H 0.636717 -0.524706 0.269732 0.122 Uiso 0.5 1 calc R . P C 2
H3AD H 0.639850 -0.405162 0.349571 0.122 Uiso 0.5 1 calc R . P C 2
H3AA H 0.634923 -0.396343 0.343073 0.122 Uiso 0.5 1 calc R . P C 1
H3AB H 0.636489 -0.531241 0.298808 0.122 Uiso 0.5 1 calc R . P C 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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
C4 S1 C18 106.5(4) . . ?
C9AA S1 C4 100.1(4) . . ?
C6 N2 C3 118.4(3) . . ?
N2 C3 C4 116.8(3) . . ?
C8 C3 N2 124.4(2) . . ?
C8 C3 C4 118.6(2) . . ?
C3 C4 S1 115.00(18) . . ?
C9 C4 S1 125.2(2) . . ?
C9 C4 C3 119.8(2) . . ?
C8 C5 H5 120.1 . . ?
C16 C5 H5 120.1 . . ?
C16 C5 C8 119.8(3) . . ?
N2 C6 H6A 121.1 . . ?
N2 C6 H6B 117.2 . . ?
N2 C6 N7 117.9(5) . . ?
N2 C6 N3AA 125.6(5) . . ?
N7 C6 H6A 121.1 . . ?
N3AA C6 H6B 117.2 . . ?
C6 N7 C0AA 118.4(9) . . ?
C26 N7 C6 126.0(9) . . ?
C26 N7 C0AA 115.3(8) . . ?
C3 C8 H8 119.5 . . ?
C5 C8 C3 121.1(3) . . ?
C5 C8 H8 119.5 . . ?
C4 C9 H9 119.7 . . ?
C4 C9 C16 120.5(2) . . ?
C16 C9 H9 119.7 . . ?
C3AA O11 C19 103.5(6) . . ?
C18 C12 H12 122.1 . . ?
C18 C12 C28 115.9(10) . . ?
C28 C12 H12 122.1 . . ?
H13A C13 H13B 109.5 . . ?
O15 C13 H13A 111.8 . . ?
O15 C13 H13B 111.8 . . ?
O15 C13 C3AA 99.8(17) . . ?
C3AA C13 H13A 111.8 . . ?
C3AA C13 H13B 111.8 . . ?
H14A C14 H14B 105.9 . . ?
C19 C14 H14A 105.2 . . ?
C19 C14 H14B 105.2 . . ?
C1 C14 H14A 105.2 . . ?
C1 C14 H14B 105.2 . . ?
C1 C14 C19 128.4(5) . . ?
C19 O15 C13 105.9(13) . . ?
C5 C16 C9 120.1(2) . . ?
C5 C16 H16 119.9 . . ?
C9 C16 H16 119.9 . . ?
C12 C18 S1 116.8(9) . . ?
C12 C18 C23 123.1(12) . . ?
C23 C18 S1 120.0(7) . . ?
O11 C19 C14 110.9(7) . . ?
O11 C19 O15 106.2(8) . . ?
O11 C19 C21 111.1(7) . . ?
C14 C19 C21 108.4(5) . . ?
O15 C19 C14 109.5(8) . . ?
O15 C19 C21 110.7(9) . . ?
H20A C20 H20B 107.1 . . ?
C0AA C20 H20A 107.8 . . ?
C0AA C20 H20B 107.8 . . ?
C0AA C20 C1AA 118.0(6) . . ?
C1AA C20 H20A 107.8 . . ?
C1AA C20 H20B 107.8 . . ?
C19 C21 H21A 107.6 . . ?
C19 C21 H21B 107.6 . . ?
H21A C21 H21B 107.1 . . ?
C4AA C21 C19 118.7(5) . . ?
C4AA C21 H21A 107.6 . . ?
C4AA C21 H21B 107.6 . . ?
H22A C22 H22B 105.8 . . ?
C26 C22 H22A 104.9 . . ?
C26 C22 H22B 104.9 . . ?
C26 C22 C1AA 129.4(7) . . ?
C1AA C22 H22A 104.9 . . ?
C1AA C22 H22B 104.9 . . ?
C18 C23 C27 113.4(8) . . ?
C18 C23 C0BA 122.3(10) . . ?
C27 C23 C0BA 124.2(10) . . ?
C27 C24 H24 120.8 . . ?
C27 C24 C28 118.3(9) . . ?
C28 C24 H24 120.8 . . ?
C8AA C25 H25 117.1 . . ?
C8AA C25 C9AA 126(2) . . ?
C9AA C25 H25 117.1 . . ?
N7 C26 H26A 107.9 . . ?
N7 C26 H26B 107.9 . . ?
C22 C26 N7 117.5(7) . . ?
C22 C26 H26A 107.9 . . ?
C22 C26 H26B 107.9 . . ?
H26A C26 H26B 107.2 . . ?
C23 C27 H27 117.8 . . ?
C24 C27 C23 124.4(10) . . ?
C24 C27 H27 117.8 . . ?
C12 C28 H28 117.6 . . ?
C24 C28 C12 124.7(8) . . ?
C24 C28 H28 117.6 . . ?
C14 C1 H1A 107.4 . . ?
C14 C1 H1B 107.4 . . ?
C14 C1 N3AA 119.9(6) . . ?
H1A C1 H1B 106.9 . . ?
N3AA C1 H1A 107.4 . . ?
N3AA C1 H1B 107.4 . . ?
N7 C0AA H0AA 105.6 . . ?
N7 C0AA H0AB 105.6 . . ?
C20 C0AA N7 127.0(7) . . ?
C20 C0AA H0AA 105.6 . . ?
C20 C0AA H0AB 105.6 . . ?
H0AA C0AA H0AB 106.1 . . ?
C20 C1AA C22 108.2(5) . . ?
O2AA C1AA C20 112.0(7) . . ?
O2AA C1AA C22 112.3(8) . . ?
O0BA C1AA C20 108.1(10) . . ?
O0BA C1AA C22 110.7(8) . . ?
O0BA C1AA O2AA 105.6(7) . . ?
C6 N3AA C1 127.8(9) . . ?
C6 N3AA C4AA 120.3(8) . . ?
C1 N3AA C4AA 111.9(8) . . ?
C1AA O2AA C3AA 107.9(5) . . ?
C21 C4AA N3AA 128.9(6) . . ?
C21 C4AA H4AA 105.1 . . ?
C21 C4AA H4AB 105.1 . . ?
N3AA C4AA H4AA 105.1 . . ?
N3AA C4AA H4AB 105.1 . . ?
H4AA C4AA H4AB 105.9 . . ?
C9AA C5AA C6AA 113.5(14) . . ?
C9AA C5AA C2AA 124.5(14) . . ?
C2AA C5AA C6AA 122.0(17) . . ?
C25 C8AA H8AA 125.1 . . ?
C7AA C8AA C25 109.8(15) . . ?
C7AA C8AA H8AA 125.1 . . ?
C8AA C7AA H7AA 110.3 . . ?
C8AA C7AA C6AA 139.4(18) . . ?
C6AA C7AA H7AA 110.3 . . ?
C25 C9AA S1 117.7(11) . . ?
C5AA C9AA S1 121.1(10) . . ?
C5AA C9AA C25 120.9(14) . . ?
C5AA C6AA H6AA 124.8 . . ?
C7AA C6AA C5AA 110.3(16) . . ?
C7AA C6AA H6AA 124.8 . . ?
C1BA O0BA C1AA 110.4(13) . . ?
O0BA C1BA H1BA 109.5 . . ?
O0BA C1BA H1BB 109.5 . . ?
O0BA C1BA C3AA 110.8(19) . . ?
H1BA C1BA H1BB 108.1 . . ?
C3AA C1BA H1BA 109.5 . . ?
C3AA C1BA H1BB 109.5 . . ?
C5AA C2AA H2AA 109.5 . . ?
C5AA C2AA H2AB 109.5 . . ?
C5AA C2AA H2AC 109.5 . . ?
H2AA C2AA H2AB 109.5 . . ?
H2AA C2AA H2AC 109.5 . . ?
H2AB C2AA H2AC 109.5 . . ?
C23 C0BA H0BA 109.5 . . ?
C23 C0BA H0BB 109.5 . . ?
C23 C0BA H0BC 109.5 . . ?
H0BA C0BA H0BB 109.5 . . ?
H0BA C0BA H0BC 109.5 . . ?
H0BB C0BA H0BC 109.5 . . ?
O11 C3AA C13 116.6(12) . . ?
O11 C3AA H3AC 108.1 . . ?
O11 C3AA H3AD 108.1 . . ?
C13 C3AA H3AC 108.1 . . ?
C13 C3AA H3AD 108.1 . . ?
O2AA C3AA H3AA 112.1 . . ?
O2AA C3AA H3AB 112.1 . . ?
C1BA C3AA O2AA 98.5(11) . . ?
C1BA C3AA H3AA 112.1 . . ?
C1BA C3AA H3AB 112.1 . . ?
H3AC C3AA H3AD 107.3 . . ?
H3AA C3AA H3AB 109.7 . . ?
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 C4 1.763(3) . ?
S1 C18 1.835(16) . ?
S1 C9AA 1.751(15) . ?
N2 C3 1.402(3) . ?
N2 C6 1.282(4) . ?
C3 C4 1.408(3) . ?
C3 C8 1.392(4) . ?
C4 C9 1.385(3) . ?
C5 H5 0.9300 . ?
C5 C8 1.386(4) . ?
C5 C16 1.377(4) . ?
C6 H6A 0.9300 . ?
C6 H6B 0.9300 . ?
C6 N7 1.452(10) . ?
C6 N3AA 1.286(12) . ?
N7 C26 1.401(14) . ?
N7 C0AA 1.460(13) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 C16 1.386(4) . ?
O11 C19 1.411(9) . ?
O11 C3AA 1.253(8) . ?
C12 H12 0.9300 . ?
C12 C18 1.367(12) . ?
C12 C28 1.426(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 O15 1.43(3) . ?
C13 C3AA 1.44(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C19 1.508(9) . ?
C14 C1 1.263(8) . ?
O15 C19 1.418(9) . ?
C16 H16 0.9300 . ?
C18 C23 1.390(18) . ?
C19 C21 1.533(8) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C0AA 1.089(8) . ?
C20 C1AA 1.504(9) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C4AA 1.251(8) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C26 1.054(8) . ?
C22 C1AA 1.539(9) . ?
C23 C27 1.477(16) . ?
C23 C0BA 1.519(11) . ?
C24 H24 0.9300 . ?
C24 C27 1.298(18) . ?
C24 C28 1.305(17) . ?
C25 H25 0.9300 . ?
C25 C8AA 1.36(2) . ?
C25 C9AA 1.411(18) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 N3AA 1.462(12) . ?
C0AA H0AA 0.9700 . ?
C0AA H0AB 0.9700 . ?
C1AA O2AA 1.425(9) . ?
C1AA O0BA 1.407(10) . ?
N3AA C4AA 1.488(13) . ?
O2AA C3AA 1.565(7) . ?
C4AA H4AA 0.9700 . ?
C4AA H4AB 0.9700 . ?
C5AA C9AA 1.359(16) . ?
C5AA C6AA 1.56(2) . ?
C5AA C2AA 1.39(2) . ?
C8AA H8AA 0.9300 . ?
C8AA C7AA 1.17(2) . ?
C7AA H7AA 0.9300 . ?
C7AA C6AA 1.39(2) . ?
C6AA H6AA 0.9300 . ?
O0BA C1BA 1.38(3) . ?
C1BA H1BA 0.9700 . ?
C1BA H1BB 0.9700 . ?
C1BA C3AA 1.51(3) . ?
C2AA H2AA 0.9600 . ?
C2AA H2AB 0.9600 . ?
C2AA H2AC 0.9600 . ?
C0BA H0BA 0.9600 . ?
C0BA H0BB 0.9600 . ?
C0BA H0BC 0.9600 . ?
C3AA H3AC 0.9700 . ?
C3AA H3AD 0.9700 . ?
C3AA H3AA 0.9700 . ?
C3AA H3AB 0.9700 . ?
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
S1 C4 C9 C16 179.3(2) . . . . ?
S1 C18 C23 C27 -177.3(8) . . . . ?
S1 C18 C23 C0BA 4.6(16) . . . . ?
N2 C3 C4 S1 5.0(3) . . . . ?
N2 C3 C4 C9 -174.3(2) . . . . ?
N2 C3 C8 C5 175.3(3) . . . . ?
N2 C6 N7 C26 6.0(13) . . . . ?
N2 C6 N7 C0AA -167.4(6) . . . . ?
N2 C6 N3AA C1 175.2(7) . . . . ?
N2 C6 N3AA C4AA -2.0(11) . . . . ?
C3 N2 C6 N7 174.6(6) . . . . ?
C3 N2 C6 N3AA -161.3(6) . . . . ?
C3 C4 C9 C16 -1.5(4) . . . . ?
C4 S1 C18 C12 97.6(10) . . . . ?
C4 S1 C18 C23 -83.1(10) . . . . ?
C4 S1 C9AA C25 -84.0(10) . . . . ?
C4 S1 C9AA C5AA 102.2(10) . . . . ?
C4 C3 C8 C5 1.0(4) . . . . ?
C4 C9 C16 C5 1.1(5) . . . . ?
C6 N2 C3 C4 -141.9(3) . . . . ?
C6 N2 C3 C8 43.6(4) . . . . ?
C6 N7 C26 C22 170.1(10) . . . . ?
C6 N7 C0AA C20 -166.4(9) . . . . ?
C6 N3AA C4AA C21 -175.8(9) . . . . ?
C8 C3 C4 S1 179.7(2) . . . . ?
C8 C3 C4 C9 0.5(4) . . . . ?
C8 C5 C16 C9 0.5(5) . . . . ?
O11 C19 C21 C4AA -141.8(8) . . . . ?
C12 C18 C23 C27 2.1(16) . . . . ?
C12 C18 C23 C0BA -176.1(12) . . . . ?
C13 O15 C19 O11 -27.5(14) . . . . ?
C13 O15 C19 C14 -147.3(12) . . . . ?
C13 O15 C19 C21 93.2(13) . . . . ?
C14 C19 C21 C4AA -19.6(11) . . . . ?
C14 C1 N3AA C6 175.6(8) . . . . ?
C14 C1 N3AA C4AA -7.0(12) . . . . ?
O15 C13 C3AA O11 1.4(16) . . . . ?
O15 C19 C21 C4AA 100.5(10) . . . . ?
C16 C5 C8 C3 -1.5(5) . . . . ?
C18 S1 C4 C3 -173.8(4) . . . . ?
C18 S1 C4 C9 5.3(4) . . . . ?
C18 C12 C28 C24 1.4(16) . . . . ?
C18 C23 C27 C24 -1.3(17) . . . . ?
C19 O11 C3AA C13 -18.1(12) . . . . ?
C19 C14 C1 N3AA -7.7(14) . . . . ?
C19 C21 C4AA N3AA 8.1(15) . . . . ?
C20 C1AA O2AA C3AA 144.3(6) . . . . ?
C20 C1AA O0BA C1BA -141.7(14) . . . . ?
C22 C1AA O2AA C3AA -93.7(7) . . . . ?
C22 C1AA O0BA C1BA 99.9(15) . . . . ?
C25 C8AA C7AA C6AA -5(3) . . . . ?
C26 N7 C0AA C20 19.6(15) . . . . ?
C26 C22 C1AA C20 17.2(16) . . . . ?
C26 C22 C1AA O2AA -106.9(12) . . . . ?
C26 C22 C1AA O0BA 135.5(12) . . . . ?
C27 C24 C28 C12 -0.7(19) . . . . ?
C28 C12 C18 S1 177.2(7) . . . . ?
C28 C12 C18 C23 -2.1(17) . . . . ?
C28 C24 C27 C23 1(2) . . . . ?
C1 C14 C19 O11 143.1(9) . . . . ?
C1 C14 C19 O15 -100.0(10) . . . . ?
C1 C14 C19 C21 20.8(12) . . . . ?
C1 N3AA C4AA C21 6.6(14) . . . . ?
C0AA N7 C26 C22 -16.3(15) . . . . ?
C0AA C20 C1AA C22 -13.6(13) . . . . ?
C0AA C20 C1AA O2AA 110.6(9) . . . . ?
C0AA C20 C1AA O0BA -133.5(10) . . . . ?
C1AA C20 C0AA N7 -2.6(15) . . . . ?
C1AA C22 C26 N7 -1.6(18) . . . . ?
C1AA O2AA C3AA C1BA -21.3(11) . . . . ?
C1AA O0BA C1BA C3AA 8(2) . . . . ?
O2AA C1AA O0BA C1BA -21.8(16) . . . . ?
C8AA C25 C9AA S1 -174.3(10) . . . . ?
C8AA C25 C9AA C5AA -1(2) . . . . ?
C8AA C7AA C6AA C5AA 1(3) . . . . ?
C9AA S1 C4 C3 169.6(5) . . . . ?
C9AA S1 C4 C9 -11.2(5) . . . . ?
C9AA C25 C8AA C7AA 5(2) . . . . ?
C9AA C5AA C6AA C7AA 4.1(18) . . . . ?
C6AA C5AA C9AA S1 169.5(9) . . . . ?
C6AA C5AA C9AA C25 -4.0(17) . . . . ?
O0BA C1AA O2AA C3AA 26.9(9) . . . . ?
O0BA C1BA C3AA O2AA 8.3(17) . . . . ?
C2AA C5AA C9AA S1 -8.0(19) . . . . ?
C2AA C5AA C9AA C25 178.4(15) . . . . ?
C2AA C5AA C6AA C7AA -178.2(16) . . . . ?
C0BA C23 C27 C24 176.8(14) . . . . ?
C3AA O11 C19 C14 146.5(5) . . . . ?
C3AA O11 C19 O15 27.6(9) . . . . ?
C3AA O11 C19 C21 -92.8(7) . . . . ?
C3AA C13 O15 C19 16.1(16) . . . . ?
