#------------------------------------------------------------------------------
#$Date: 2025-11-12 00:56:30 +0200 (Wed, 12 Nov 2025) $
#$Revision: 303253 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/51/7135161.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_7135161
loop_
_publ_author_name
'Yadav, Anup Kumar'
'Kumar, Vipin'
'Singh, Saurabh'
'Samai, Subhasis'
'Singh, Maya Shankar'
_publ_section_title
;
 Synthesis of pyrrolo[3,4-c]pyridines via metal-free
 cross-coupling/cyclization cascades of β-ketothioamides with
 2aroylmalononitrile at room temperature
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D5CC04230E
_journal_year                    2025
_chemical_formula_moiety         'C27 H19 N3 O2 S, C2 H6 O S, H2 O'
_chemical_formula_sum            'C29 H27 N3 O4 S2'
_chemical_formula_weight         545.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-24
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-07-25 deposited with the CCDC.	2025-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.8060(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.6291(2)
_cell_length_b                   8.63670(10)
_cell_length_c                   30.4166(2)
_cell_measurement_reflns_used    20888
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.8010
_cell_measurement_theta_min      2.4010
_cell_volume                     5661.97(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    105.00 170.00   0.50    0.20    --   96.04  96.00-150.00  130
  2  ω    105.00 170.00   0.50    0.20    --   96.04  96.00 120.00  130
  3  ω    -25.00  44.00   0.50    0.20    --   40.83 -39.00  92.00  138
  4  ω    -27.00  37.00   0.50    0.20    --   40.83 -32.00   0.00  128
  5  ω    -27.00  64.00   0.50    0.20    --   40.83 -65.00 -60.00  182
  6  ω     44.00 127.00   0.50    0.20    --   96.04-145.00 -30.00  166
  7  ω     41.00 100.00   0.50    0.20    --   40.83-138.00-120.00  118
  8  ω     23.00 106.00   0.50    0.20    --   96.04 -96.00 -60.00  166
  9  ω     41.00 100.00   0.50    0.20    --   40.83-138.00 150.00  118
 10  ω     26.00 127.00   0.50    0.20    --   96.04 -87.00 120.00  202
 11  ω     32.00 110.00   0.50    0.20    --   96.04-117.00  90.00  156
 12  ω     27.00 105.00   0.50    0.20    --   96.04 -77.00  30.00  156
 13  ω     28.00  83.00   0.50    0.20    --   96.04 -68.00   0.00  110
 14  ω     28.00  83.00   0.50    0.20    --   96.04 -68.00 -60.00  110
 15  ω     29.00  57.00   0.50    0.20    --   96.04 -50.00 -60.00   56
 16  ω     28.00  83.00   0.50    0.20    --   96.04 -68.00 -90.00  110
 17  ω     29.00  57.00   0.50    0.20    --   96.04 -50.00-150.00   56
 18  ω     28.00  68.00   0.50    0.20    --   96.04 -59.00-180.00   80
 19  ω     28.00  68.00   0.50    0.20    --   96.04 -59.00-150.00   80
 20  ω     29.00  57.00   0.50    0.20    --   96.04 -50.00 -30.00   56
 21  ω     29.00  57.00   0.50    0.20    --   96.04 -50.00   0.00   56
 22  ω     29.00  57.00   0.50    0.20    --   96.04 -50.00  60.00   56
 23  ω     29.00  57.00   0.50    0.20    --   96.04 -50.00  90.00   56
 24  ω     29.00  57.00   0.50    0.20    --   96.04 -50.00 120.00   56
 25  ω     29.00  57.00   0.50    0.20    --   96.04 -50.00 150.00   56
 26  ω     82.00 164.00   0.50    0.20    --   96.04  33.00  90.00  164
 27  ω     74.00 163.00   0.50    0.20    --   96.04  59.00 120.00  178
 28  ω     69.00 165.00   0.50    0.20    --   96.04  77.00  90.00  192
 29  ω     74.00 163.00   0.50    0.20    --   96.04  59.00 150.00  178
 30  ω     74.00 163.00   0.50    0.20    --   96.04  59.00  30.00  178
 31  ω     69.00 165.00   0.50    0.20    --   96.04  77.00  60.00  192
 32  ω     69.00 165.00   0.50    0.20    --   96.04  77.00   0.00  192
 33  ω     77.00 163.00   0.50    0.20    --   96.04  50.00 -30.00  172
 34  ω     79.00 162.00   0.50    0.20    --   96.04  42.00 -60.00  166
 35  ω     74.00 163.00   0.50    0.20    --   96.04  59.00 -90.00  178
 36  ω     74.00 163.00   0.50    0.20    --   96.04  59.00-150.00  178
 37  ω     77.00 163.00   0.50    0.20    --   96.04  50.00-180.00  172
 38  ω     80.00 162.00   0.50    0.20    --   96.04  39.00-113.00  164
 39  ω     79.00 162.00   0.50    0.20    --   96.04  42.00   0.00  166
 40  ω     28.00 109.00   0.50    0.20    --   40.83  32.00  90.00  162
 41  ω     14.00 110.00   0.50    0.20    --   40.83  77.00 150.00  192
 42  ω     21.00 108.00   0.50    0.20    --   40.83  54.00   0.00  174
 43  ω     14.00 110.00   0.50    0.20    --   40.83  77.00   0.00  192
 44  ω     14.00 110.00   0.50    0.20    --   40.83  77.00 -90.00  192
 45  ω     14.00 110.00   0.50    0.20    --   40.83  77.00-150.00  192
 46  ω     25.00 107.00   0.50    0.20    --   40.83  39.00-113.00  164
 47  ω     21.00 108.00   0.50    0.20    --   40.83  54.00 150.00  174
 48  ω    -24.00  35.00   0.50    0.20    --  -40.83  11.00   0.00  118
 49  ω    -47.00 -15.00   0.50    0.20    --  -82.50  42.00  30.00   64
 50  ω    -47.00 -15.00   0.50    0.20    --  -82.50  42.00 -90.00   64
 51  ω    -44.00 -16.00   0.50    0.20    --  -82.50  39.00-113.00   56
 52  ω    -44.00  25.00   0.50    0.20    --  -40.83  39.00-113.00  138
 53  ω    -61.00  26.00   0.50    0.20    --  -40.83  54.00-120.00  174
 54  ω    -84.00 -18.00   0.50    0.20    --  -82.50 117.00 -90.00  132
 55  ω   -109.00 -14.00   0.50    0.20    --  -40.83 -77.00 -90.00  190
 56  ω   -109.00 -14.00   0.50    0.20    --  -40.83 -77.00   0.00  190
 57  ω   -109.00 -14.00   0.50    0.20    --  -40.83 -77.00  30.00  190
 58  ω   -109.00 -14.00   0.50    0.20    --  -40.83 -77.00  60.00  190
 59  ω   -107.00 -25.00   0.50    0.20    --  -40.83 -39.00  92.00  164
 60  ω   -148.00 -67.00   0.50    0.20    --  -82.50 -39.00  92.00  162
 61  ω   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00 -30.00  192
 62  ω   -151.00 -83.00   0.50    0.20    --  -82.50 -77.00 -60.00  136
 63  ω   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00-120.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0623142000
_diffrn_orient_matrix_UB_12      0.0856842000
_diffrn_orient_matrix_UB_13      -0.0011340000
_diffrn_orient_matrix_UB_21      -0.0047145000
_diffrn_orient_matrix_UB_22      -0.0140163000
_diffrn_orient_matrix_UB_23      -0.0506606000
_diffrn_orient_matrix_UB_31      -0.0346934000
_diffrn_orient_matrix_UB_32      0.1558274000
_diffrn_orient_matrix_UB_33      -0.0039292000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            45758
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.089
_diffrn_reflns_theta_min         2.916
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.020
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       block
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.102
_refine_diff_density_max         1.143
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         5159
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0811P)²+3.8154P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1434
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4394
_reflns_number_total             5159
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc04230e3.cif
_cod_data_source_block           4me-cn2_auto
_cod_database_code               7135161
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O S'
_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   0.820
_shelx_estimated_absorpt_t_min   0.743
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 S2-O3 \\sim S2A-O3A
 with sigma of 0.02
 S2-C29 \\sim S2A-C29A
 with sigma of 0.02
 S2-C28 \\sim S2A-C28A
 with sigma of 0.02
 O3-C29 \\sim O3A-C29A
 with sigma of 0.04
 O3-C28 \\sim O3A-C28A
 with sigma of 0.04
 C29-C28 \\sim C29A-C28A
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 C28A, S2, O3, C29, C28, C29A, S2A, O3A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(C28A)=Sof(H28D)=Sof(H28E)=Sof(H28F)=Sof(S2A)=Sof(O3A)=Sof(C29A)=Sof(H29D)=
 Sof(H29E)=Sof(H29F)=1-FVAR(1)
 Sof(S2)=Sof(O3)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=Sof(C28)=Sof(H28A)=
 Sof(H28B)=Sof(H28C)=FVAR(1)
5.a Free rotating group:
 O4(H4A,H4B)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C16(H16), C13(H13), C14(H14), C24(H24), C15(H15), C19(H19),
 C10(H10), C20(H20), C6(H6), C23(H23), C8(H8), C9(H9), C7(H7)
5.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C29(H29A,H29B,H29C), C28(H28A,H28B,H28C), C28A(H28D,H28E,
 H28F), C29A(H29D,H29E,H29F)
5.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.229
_oxdiff_exptl_absorpt_empirical_full_min 0.830
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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 0.67877(3) 0.48444(8) 0.42396(2) 0.0637(2) Uani 1 1 d . . . . .
S2 S 0.59502(9) 1.1577(2) 0.28715(6) 0.0613(4) Uani 0.813(5) 1 d D U P A 1
O2 O 0.85825(7) 0.39036(17) 0.34118(5) 0.0508(4) Uani 1 1 d . . . . .
H2 H 0.8276 0.3706 0.3232 0.076 Uiso 1 1 calc R U . . .
N1 N 0.79240(7) 0.43789(18) 0.39900(5) 0.0388(3) Uani 1 1 d . . . . .
N2 N 0.72837(8) 0.8575(2) 0.31763(6) 0.0461(4) Uani 1 1 d . . . . .
O1 O 0.79497(8) 0.9303(2) 0.26758(6) 0.0750(5) Uani 1 1 d . . . . .
O4 O 0.75079(9) 0.3523(2) 0.29533(6) 0.0729(5) Uani 1 1 d G . . . .
H4A H 0.7275 0.2728 0.2930 0.109 Uiso 1 1 d G U . . .
H4B H 0.7388 0.4078 0.2732 0.109 Uiso 1 1 d G U . . .
O3 O 0.66296(15) 1.1137(5) 0.28811(12) 0.0667(9) Uani 0.813(5) 1 d D U P A 1
C3 C 0.80698(8) 0.6358(2) 0.34996(6) 0.0381(4) Uani 1 1 d . . . . .
C4 C 0.84132(8) 0.4986(2) 0.37170(6) 0.0400(4) Uani 1 1 d . . . . .
C2 C 0.74857(8) 0.6512(2) 0.36654(6) 0.0379(4) Uani 1 1 d . . . . .
C17 C 0.70900(8) 0.7664(2) 0.35033(6) 0.0390(4) Uani 1 1 d . . . . .
C11 C 0.80210(8) 0.2966(2) 0.42345(6) 0.0399(4) Uani 1 1 d . . . . .
C26 C 0.82578(9) 0.7288(2) 0.31751(6) 0.0442(4) Uani 1 1 d . . . . .
C18 C 0.64683(9) 0.8045(2) 0.36439(6) 0.0425(4) Uani 1 1 d . . . . .
C1 C 0.73984(8) 0.5224(2) 0.39730(6) 0.0394(4) Uani 1 1 d . . . . .
C5 C 0.89828(9) 0.5473(2) 0.40137(7) 0.0464(5) Uani 1 1 d . . . . .
C25 C 0.78398(10) 0.8461(2) 0.29843(7) 0.0501(5) Uani 1 1 d . . . . .
C12 C 0.81807(11) 0.3015(3) 0.46831(7) 0.0538(5) Uani 1 1 d . . . . .
H12 H 0.8220 0.3981 0.4832 0.065 Uiso 1 1 calc R U . . .
C16 C 0.79595(11) 0.1571(2) 0.40191(7) 0.0534(5) Uani 1 1 d . . . . .
H16 H 0.7842 0.1539 0.3711 0.064 Uiso 1 1 calc R U . . .
C27 C 0.88500(10) 0.7160(3) 0.29995(7) 0.0568(6) Uani 1 1 d . . . . .
N3 N 0.93162(10) 0.7084(4) 0.28532(8) 0.0856(8) Uani 1 1 d . . . . .
C13 C 0.82832(12) 0.1646(3) 0.49145(7) 0.0619(6) Uani 1 1 d . . . . .
H13 H 0.8390 0.1673 0.5224 0.074 Uiso 1 1 calc R U . . .
C14 C 0.82311(11) 0.0252(3) 0.46998(8) 0.0569(6) Uani 1 1 d . . . . .
H14 H 0.8307 -0.0685 0.4859 0.068 Uiso 1 1 calc R U . . .
C24 C 0.59500(10) 0.7876(3) 0.33535(8) 0.0579(6) Uani 1 1 d . . . . .
H24 H 0.5987 0.7477 0.3066 0.070 Uiso 1 1 calc R U . . .
C15 C 0.80692(12) 0.0212(3) 0.42532(8) 0.0603(6) Uani 1 1 d . . . . .
H15 H 0.8032 -0.0754 0.4104 0.072 Uiso 1 1 calc R U . . .
C19 C 0.63995(11) 0.8634(3) 0.40584(8) 0.0645(6) Uani 1 1 d . . . . .
H19 H 0.6753 0.8748 0.4263 0.077 Uiso 1 1 calc R U . . .
C10 C 0.89151(12) 0.6349(3) 0.43867(9) 0.0639(6) Uani 1 1 d . . . . .
H10 H 0.8513 0.6660 0.4456 0.077 Uiso 1 1 calc R U . . .
C21 C 0.52976(11) 0.8883(3) 0.38908(10) 0.0703(7) Uani 1 1 d . . . . .
C20 C 0.58233(12) 0.9057(4) 0.41779(9) 0.0752(8) Uani 1 1 d . . . . .
H20 H 0.5786 0.9478 0.4463 0.090 Uiso 1 1 calc R U . . .
C6 C 0.95664(10) 0.5026(4) 0.39161(9) 0.0705(7) Uani 1 1 d . . . . .
H6 H 0.9617 0.4429 0.3659 0.085 Uiso 1 1 calc R U . . .
C23 C 0.53716(11) 0.8292(4) 0.34826(9) 0.0748(8) Uani 1 1 d . . . . .
H23 H 0.5017 0.8160 0.3280 0.090 Uiso 1 1 calc R U . . .
C8 C 1.00147(15) 0.6313(4) 0.45597(14) 0.0974(12) Uani 1 1 d . . . . .
H8 H 1.0370 0.6601 0.4747 0.117 Uiso 1 1 calc R U . . .
C9 C 0.94321(16) 0.6775(4) 0.46603(11) 0.0885(9) Uani 1 1 d . . . . .
H9 H 0.9386 0.7381 0.4916 0.106 Uiso 1 1 calc R U . . .
C7 C 1.00814(13) 0.5449(5) 0.41946(13) 0.0971(11) Uani 1 1 d . . . . .
H7 H 1.0484 0.5131 0.4128 0.116 Uiso 1 1 calc R U . . .
C22 C 0.46594(14) 0.9359(5) 0.40175(15) 0.1195(14) Uani 1 1 d . . . . .
H22A H 0.4544 0.8713 0.4263 0.179 Uiso 1 1 calc R U . . .
H22B H 0.4354 0.9221 0.3764 0.179 Uiso 1 1 calc R U . . .
H22C H 0.4668 1.0448 0.4108 0.179 Uiso 1 1 calc R U . . .
C29 C 0.58692(19) 1.3152(6) 0.24996(14) 0.0912(13) Uani 0.813(5) 1 d D U P A 1
H29A H 0.6172 1.3956 0.2592 0.137 Uiso 0.813(5) 1 calc R U P A 1
H29B H 0.5449 1.3577 0.2498 0.137 Uiso 0.813(5) 1 calc R U P A 1
H29C H 0.5942 1.2795 0.2202 0.137 Uiso 0.813(5) 1 calc R U P A 1
C28 C 0.5854(2) 1.2589(6) 0.33593(13) 0.0939(13) Uani 0.813(5) 1 d D U P A 1
H28A H 0.5934 1.1893 0.3612 0.141 Uiso 0.813(5) 1 calc R U P A 1
H28B H 0.5428 1.2983 0.3352 0.141 Uiso 0.813(5) 1 calc R U P A 1
H28C H 0.6146 1.3459 0.3387 0.141 Uiso 0.813(5) 1 calc R U P A 1
H2A H 0.7070(12) 0.931(3) 0.3091(8) 0.063(7) Uiso 1 1 d . . . . .
C28A C 0.5988(8) 1.3832(15) 0.3102(6) 0.088(4) Uani 0.187(5) 1 d D U P A 2
H28D H 0.6366 1.4164 0.3276 0.131 Uiso 0.187(5) 1 calc R U P A 2
H28E H 0.5624 1.4121 0.3255 0.131 Uiso 0.187(5) 1 calc R U P A 2
H28F H 0.5966 1.4335 0.2812 0.131 Uiso 0.187(5) 1 calc R U P A 2
S2A S 0.6002(4) 1.1815(10) 0.3033(3) 0.0699(19) Uani 0.187(5) 1 d D U P A 2
O3A O 0.6664(7) 1.134(2) 0.3043(5) 0.066(3) Uani 0.187(5) 1 d D U P A 2
C29A C 0.5689(8) 1.190(2) 0.2480(5) 0.088(4) Uani 0.187(5) 1 d D U P A 2
H29D H 0.5295 1.2470 0.2464 0.132 Uiso 0.187(5) 1 calc R U P A 2
H29E H 0.5617 1.0852 0.2366 0.132 Uiso 0.187(5) 1 calc R U P A 2
H29F H 0.5980 1.2440 0.2302 0.132 Uiso 0.187(5) 1 calc R U 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
O3 S2 C29 104.4(2) . . ?
O3 S2 C28 107.05(19) . . ?
C28 S2 C29 98.4(2) . . ?
C4 O2 H2 109.5 . . ?
C11 N1 C4 120.45(14) . . ?
C1 N1 C4 115.01(14) . . ?
C1 N1 C11 124.50(15) . . ?
C17 N2 C25 126.76(17) . . ?
C17 N2 H2A 118.8(18) . . ?
C25 N2 H2A 114.3(18) . . ?
H4A O4 H4B 104.5 . . ?
C2 C3 C4 109.82(15) . . ?
C26 C3 C4 127.65(16) . . ?
C26 C3 C2 122.43(17) . . ?
O2 C4 N1 111.99(15) . . ?
O2 C4 C3 112.38(15) . . ?
O2 C4 C5 109.66(15) . . ?
N1 C4 C3 99.92(13) . . ?
N1 C4 C5 110.04(15) . . ?
C3 C4 C5 112.56(16) . . ?
C3 C2 C1 108.80(15) . . ?
C17 C2 C3 119.39(16) . . ?
C17 C2 C1 131.55(17) . . ?
N2 C17 C2 117.35(16) . . ?
N2 C17 C18 115.14(16) . . ?
C2 C17 C18 127.52(17) . . ?
C12 C11 N1 119.99(18) . . ?
C16 C11 N1 119.66(17) . . ?
C16 C11 C12 120.34(18) . . ?
C3 C26 C25 119.32(17) . . ?
C3 C26 C27 123.75(18) . . ?
C27 C26 C25 116.92(17) . . ?
C24 C18 C17 120.10(18) . . ?
C24 C18 C19 118.79(19) . . ?
C19 C18 C17 121.05(18) . . ?
N1 C1 S1 125.73(14) . . ?
N1 C1 C2 106.29(15) . . ?
C2 C1 S1 127.98(14) . . ?
C10 C5 C4 120.09(18) . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 C10 119.5(2) . . ?
N2 C25 C26 114.64(17) . . ?
O1 C25 N2 120.79(19) . . ?
O1 C25 C26 124.57(19) . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.5(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C16 H16 120.2 . . ?
C11 C16 C15 119.6(2) . . ?
C15 C16 H16 120.2 . . ?
N3 C27 C26 178.4(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.8(2) . . ?
C15 C14 H14 120.1 . . ?
C18 C24 H24 120.1 . . ?
C18 C24 C23 119.7(2) . . ?
C23 C24 H24 120.1 . . ?
C16 C15 H15 119.8 . . ?
C14 C15 C16 120.4(2) . . ?
C14 C15 H15 119.8 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.6(2) . . ?
C20 C19 H19 119.7 . . ?
C5 C10 H10 119.9 . . ?
C5 C10 C9 120.2(3) . . ?
C9 C10 H10 119.9 . . ?
C20 C21 C22 121.8(3) . . ?
C23 C21 C20 117.5(2) . . ?
C23 C21 C22 120.7(3) . . ?
C19 C20 C21 121.3(2) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.8(3) . . ?
C7 C6 H6 120.1 . . ?
C24 C23 H23 119.0 . . ?
C21 C23 C24 122.1(2) . . ?
C21 C23 H23 119.0 . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 C10 119.7(3) . . ?
C8 C9 H9 120.1 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
S2 C29 H29A 109.5 . . ?
S2 C29 H29B 109.5 . . ?
S2 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
S2 C28 H28A 109.5 . . ?
S2 C28 H28B 109.5 . . ?
S2 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
H28D C28A H28E 109.5 . . ?
H28D C28A H28F 109.5 . . ?
H28E C28A H28F 109.5 . . ?
S2A C28A H28D 109.5 . . ?
S2A C28A H28E 109.5 . . ?
S2A C28A H28F 109.5 . . ?
C28A S2A C29A 93.5(9) . . ?
O3A S2A C28A 107.2(10) . . ?
O3A S2A C29A 109.0(9) . . ?
S2A C29A H29D 109.5 . . ?
S2A C29A H29E 109.5 . . ?
S2A C29A H29F 109.5 . . ?
H29D C29A H29E 109.5 . . ?
H29D C29A H29F 109.5 . . ?
H29E C29A H29F 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 C1 1.6400(19) . ?
S2 O3 1.516(3) . ?
S2 C29 1.768(4) . ?
S2 C28 1.749(4) . ?
O2 H2 0.8400 . ?
O2 C4 1.388(2) . ?
N1 C4 1.494(2) . ?
N1 C11 1.435(2) . ?
N1 C1 1.348(2) . ?
N2 C17 1.362(2) . ?
N2 C25 1.384(3) . ?
N2 H2A 0.81(3) . ?
O1 C25 1.226(2) . ?
O4 H4A 0.8507 . ?
O4 H4B 0.8496 . ?
C3 C4 1.520(2) . ?
C3 C2 1.406(2) . ?
C3 C26 1.361(3) . ?
C4 C5 1.524(3) . ?
C2 C17 1.376(3) . ?
C2 C1 1.476(2) . ?
C17 C18 1.482(3) . ?
C11 C12 1.380(3) . ?
C11 C16 1.372(3) . ?
C26 C25 1.447(3) . ?
C26 C27 1.433(3) . ?
C18 C24 1.376(3) . ?
C18 C19 1.379(3) . ?
C5 C10 1.382(3) . ?
C5 C6 1.376(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.383(3) . ?
C27 N3 1.138(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.370(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.375(3) . ?
C24 H24 0.9500 . ?
C24 C23 1.389(3) . ?
C15 H15 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.377(3) . ?
C10 H10 0.9500 . ?
C10 C9 1.387(4) . ?
C21 C20 1.383(4) . ?
C21 C23 1.364(4) . ?
C21 C22 1.520(3) . ?
C20 H20 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.391(4) . ?
C23 H23 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.380(5) . ?
C8 C7 1.356(5) . ?
C9 H9 0.9500 . ?
C7 H7 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C28A H28D 0.9800 . ?
C28A H28E 0.9800 . ?
C28A H28F 0.9800 . ?
C28A S2A 1.755(13) . ?
S2A O3A 1.486(12) . ?
S2A C29A 1.760(14) . ?
C29A H29D 0.9800 . ?
C29A H29E 0.9800 . ?
C29A H29F 0.9800 . ?
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
O2 C4 C5 C10 -169.58(19) . . . . ?
O2 C4 C5 C6 9.5(3) . . . . ?
N1 C4 C5 C10 -46.0(2) . . . . ?
N1 C4 C5 C6 133.1(2) . . . . ?
N1 C11 C12 C13 -178.9(2) . . . . ?
N1 C11 C16 C15 178.3(2) . . . . ?
N2 C17 C18 C24 64.5(3) . . . . ?
N2 C17 C18 C19 -112.7(2) . . . . ?
C3 C4 C5 C10 64.5(2) . . . . ?
C3 C4 C5 C6 -116.4(2) . . . . ?
C3 C2 C17 N2 1.9(3) . . . . ?
C3 C2 C17 C18 -177.90(18) . . . . ?
C3 C2 C1 S1 -177.68(15) . . . . ?
C3 C2 C1 N1 1.4(2) . . . . ?
C3 C26 C25 N2 3.5(3) . . . . ?
C3 C26 C25 O1 -176.0(2) . . . . ?
C4 N1 C11 C12 102.0(2) . . . . ?
C4 N1 C11 C16 -77.4(2) . . . . ?
C4 N1 C1 S1 -179.61(14) . . . . ?
C4 N1 C1 C2 1.3(2) . . . . ?
C4 C3 C2 C17 -178.27(16) . . . . ?
C4 C3 C2 C1 -3.4(2) . . . . ?
C4 C3 C26 C25 174.80(19) . . . . ?
C4 C3 C26 C27 -3.8(3) . . . . ?
C4 C5 C10 C9 179.1(2) . . . . ?
C4 C5 C6 C7 -178.6(2) . . . . ?
C2 C3 C4 O2 122.74(17) . . . . ?
C2 C3 C4 N1 3.84(19) . . . . ?
C2 C3 C4 C5 -112.86(18) . . . . ?
C2 C3 C26 C25 -1.4(3) . . . . ?
C2 C3 C26 C27 179.9(2) . . . . ?
C2 C17 C18 C24 -115.6(2) . . . . ?
C2 C17 C18 C19 67.1(3) . . . . ?
C17 N2 C25 O1 176.3(2) . . . . ?
C17 N2 C25 C26 -3.3(3) . . . . ?
C17 C2 C1 S1 -3.7(3) . . . . ?
C17 C2 C1 N1 175.37(19) . . . . ?
C17 C18 C24 C23 -177.6(2) . . . . ?
C17 C18 C19 C20 176.7(2) . . . . ?
C11 N1 C4 O2 55.6(2) . . . . ?
C11 N1 C4 C3 174.81(16) . . . . ?
C11 N1 C4 C5 -66.6(2) . . . . ?
C11 N1 C1 S1 2.5(3) . . . . ?
C11 N1 C1 C2 -176.56(16) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C11 C16 C15 C14 0.8(4) . . . . ?
C26 C3 C4 O2 -53.9(3) . . . . ?
C26 C3 C4 N1 -172.75(19) . . . . ?
C26 C3 C4 C5 70.5(2) . . . . ?
C26 C3 C2 C17 -1.5(3) . . . . ?
C26 C3 C2 C1 173.40(18) . . . . ?
C18 C24 C23 C21 0.6(4) . . . . ?
C18 C19 C20 C21 1.1(5) . . . . ?
C1 N1 C4 O2 -122.34(17) . . . . ?
C1 N1 C4 C3 -3.2(2) . . . . ?
C1 N1 C4 C5 115.42(18) . . . . ?
C1 N1 C11 C12 -80.2(2) . . . . ?
C1 N1 C11 C16 100.4(2) . . . . ?
C1 C2 C17 N2 -171.58(19) . . . . ?
C1 C2 C17 C18 8.6(3) . . . . ?
C5 C10 C9 C8 -0.3(4) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C25 N2 C17 C2 0.6(3) . . . . ?
C25 N2 C17 C18 -179.6(2) . . . . ?
C12 C11 C16 C15 -1.1(3) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C16 C11 C12 C13 0.5(3) . . . . ?
C27 C26 C25 N2 -177.7(2) . . . . ?
C27 C26 C25 O1 2.7(4) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C24 C18 C19 C20 -0.6(4) . . . . ?
C19 C18 C24 C23 -0.3(4) . . . . ?
C10 C5 C6 C7 0.4(4) . . . . ?
C20 C21 C23 C24 -0.1(4) . . . . ?
C6 C5 C10 C9 0.0(4) . . . . ?
C23 C21 C20 C19 -0.7(4) . . . . ?
C9 C8 C7 C6 0.4(5) . . . . ?
C7 C8 C9 C10 0.1(5) . . . . ?
C22 C21 C20 C19 -179.5(3) . . . . ?
C22 C21 C23 C24 178.6(3) . . . . ?
