#------------------------------------------------------------------------------
#$Date: 2020-08-07 02:26:41 +0300 (Fri, 07 Aug 2020) $
#$Revision: 255142 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/86/4038654.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_4038654
loop_
_publ_author_name
'Dressler, Justin'
'Barker, Joshua E.'
'Karas, Lucas J.'
'Hashimoto, Hannah'
'Kishi, Ryohei'
'Zakharov, Lev N.'
'MacMillan, Samantha N.'
'Gómez-García, Carlos J'
'Nakano, Masayoshi'
'Wu, Judy I.'
'Haley, Michael M.'
_publ_section_title
;
 Late-stage Modification of Electronic Properties of Antiaromatic and
 Diradicaloid Indeno[1,2-b]fluorene Analogues via Sulfur Oxidation.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01387
_journal_year                    2020
_chemical_formula_moiety         'C52 H46 O4 S2, 2(C2 H3 N)'
_chemical_formula_sum            'C56 H52 N2 O4 S2'
_chemical_formula_weight         881.11
_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     dual
_audit_creation_date             2019-10-03
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_cell_angle_alpha                92.525(2)
_cell_angle_beta                 97.786(2)
_cell_angle_gamma                98.462(2)
_cell_formula_units_Z            1
_cell_length_a                   7.62440(10)
_cell_length_b                   10.3907(2)
_cell_length_c                   15.0797(3)
_cell_measurement_reflns_used    11179
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      76.9070
_cell_measurement_theta_min      5.9390
_cell_volume                     1168.26(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -69.00  22.00   0.50    1.92    --  -49.81  77.00  60.00  182
  2  ω    -27.00  22.00   0.50    1.92    --  -49.81  19.00 150.00   98
  3  ω    -81.00   7.00   0.50    1.92    --  -49.81 103.00 -10.00  176
  4  ω    -51.00 -11.00   0.50    7.69    --  -82.50  45.00 -60.00   80
  5  ω    -81.00 -11.00   0.50    7.69    --  -82.50 103.00 -10.00  140
  6  ω    -22.00  27.00   0.50    1.92    --   49.81 -19.00 -30.00   98
  7  ω    -21.00  42.00   0.50    1.92    --   49.81 -37.00 -90.00  126
  8  ω     15.00  82.00   0.50    1.92    --   49.81-103.00-112.00  134
  9  ω     32.00 107.00   0.50    7.69    --  104.00-103.00-112.00  150
 10  ω     77.00 103.00   0.50    7.69    --  104.00 -94.00-120.00   52
 11  ω     73.00 112.00   0.50    7.69    --  104.00-125.00-180.00   78
 12  ω     70.00 105.00   0.50    7.69    --  104.00 -94.00 -90.00   70
 13  ω     94.00 119.00   0.50    7.69    --  104.00 -85.00 -51.16   50
 14  ω     80.00 107.00   0.50    7.69    --  104.00-105.00  29.90   54
 15  ω     73.00 102.00   0.50    7.69    --  104.00 -94.00  30.00   58
 16  ω     71.00 105.00   0.50    7.69    --  104.00 -77.00  60.00   68
 17  ω     64.00 110.00   0.50    7.69    --  104.00-125.00  30.00   92
 18  ω     55.00 105.00   0.50    7.69    --  104.00 -94.00  60.00  100
 19  ω     81.00 107.00   0.50    7.69    --  104.00 -81.00 133.74   52
 20  ω     79.00 106.00   0.50    7.69    --  104.00 -94.00 150.00   54
 21  ω     79.00 112.00   0.50    7.69    --  104.00-125.00 150.00   66
 22  ω     43.00  68.00   0.50    7.69    --  104.00 -61.00  90.00   50
 23  ω     38.00  74.00   0.50    7.69    --  104.00-105.00  29.90   72
 24  ω     51.00 110.00   0.50    7.69    --  104.00-125.00  60.00  118
 25  ω     41.00  67.00   0.50    7.69    --  104.00 -94.00 -30.00   52
 26  ω     37.00  63.00   0.50    7.69    --  104.00-125.00   0.00   52
 27  ω     32.00 106.00   0.50    7.69    --  104.00 -94.00 -60.00  148
 28  ω     82.00 107.00   0.50    7.69    --  104.00 -78.00 -90.17   50
 29  ω     59.00  98.00   0.50    7.69    --  104.00   0.00-150.00   78
 30  ω    126.00 152.00   0.50    7.69    --  104.00  15.00-180.00   52
 31  ω    131.00 171.00   0.50    7.69    --  104.00  77.00-180.00   80
 32  ω    144.00 170.00   0.50    7.69    --  104.00 125.00-180.00   52
 33  ω    104.00 130.00   0.50    7.69    --  104.00  45.00 -60.00   52
 34  ω    135.00 168.00   0.50    7.69    --  104.00  45.00 -60.00   66
 35  ω    119.00 147.00   0.50    7.69    --  104.00  15.00   0.00   56
 36  ω    140.00 166.00   0.50    7.69    --  104.00  45.00  90.00   52
 37  ω    112.00 138.00   0.50    7.69    --  104.00  15.00  90.00   52
 38  ω    106.00 176.00   0.50    7.69    --  104.00 103.00 -10.00  140
 39  ω     95.00 176.00   0.50    7.69    --  104.00 125.00 -60.00  162
 40  ω    105.00 141.00   0.50    7.69    --  104.00 125.00  90.00   72
 41  ω     60.00  93.00   0.50    7.69    --  104.00   0.00 150.00   66
 42  ω     40.00  70.00   0.50    7.69    --  104.00 -77.00 150.00   60
 43  ω     33.00  64.00   0.50    7.69    --  104.00 -61.00 150.00   62
 44  ω     36.00  65.00   0.50    7.69    --  104.00 -94.00  90.00   58
 45  ω     41.00  67.00   0.50    7.69    --  104.00-125.00 150.00   52
 46  ω     33.00  59.00   0.50    7.69    --  104.00 -94.00 120.00   52
 47  ω     32.00  71.00   0.50    7.69    --  104.00 -61.00  60.00   78
 48  ω     33.00  63.00   0.50    7.69    --  104.00  -3.00 131.92   60
 49  ω     36.00  63.00   0.50    7.69    --  104.00 -61.00 120.00   54
 50  ω     32.00 106.00   0.50    7.69    --  104.00 -77.00  30.00  148
 51  ω     34.00 112.00   0.50    7.69    --  104.00-125.00 -60.00  156
 52  ω     34.00 112.00   0.50    7.69    --  104.00-125.00-120.00  156
 53  ω     32.00  71.00   0.50    7.69    --  104.00 -61.00  30.00   78
 54  ω     32.00  73.00   0.50    7.69    --  104.00 -68.00  -6.21   82
 55  ω     33.00  70.00   0.50    7.69    --  104.00 -61.00 -60.00   74
 56  ω     32.00  60.00   0.50    7.69    --  104.00 -77.00-120.00   56
 57  ω     35.00  61.00   0.50    7.69    --  104.00 -78.00 -90.17   52
 58  ω     35.00  80.00   0.50    7.69    --  104.00-125.00-150.00   90
 59  ω     87.00 167.00   0.50    7.69    --  104.00  77.00-150.00  160
 60  ω     94.00 126.00   0.50    7.69    --  104.00  77.00-180.00   64
 61  ω     88.00 170.00   0.50    7.69    --  104.00  77.00-120.00  164
 62  ω   -120.00 -73.00   0.50    1.92    --  -49.81-125.00 -60.00   94
 63  ω   -120.00 -73.00   0.50    1.92    --  -49.81-125.00   0.00   94
 64  ω   -120.00 -73.00   0.50    1.92    --  -49.81-125.00  60.00   94
 65  ω   -154.00 -84.00   0.50    7.69    --  -82.50-103.00-112.00  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0845278000
_diffrn_orient_matrix_UB_12      -0.1170229000
_diffrn_orient_matrix_UB_13      0.0473135000
_diffrn_orient_matrix_UB_21      -0.1262515000
_diffrn_orient_matrix_UB_22      -0.0488003000
_diffrn_orient_matrix_UB_23      -0.0873679000
_diffrn_orient_matrix_UB_31      0.1397328000
_diffrn_orient_matrix_UB_32      -0.0805537000
_diffrn_orient_matrix_UB_33      -0.0283888000
_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  0.0318
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24859
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.503
_diffrn_reflns_theta_min         4.311
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.418
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.775
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.58a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear red'
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       plate
_exptl_crystal_F_000             466
_exptl_crystal_size_max          0.136
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0427
_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)+(0.0444P)²+0.9080P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1063
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4367
_reflns_number_total             4765
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01387_si_004.cif
_cod_data_source_block           rjd1_abs
_cod_database_code               4038654
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C56H52N2O4S2
_chemical_oxdiff_usercomment     'Crystallized from CHCl3/MeCN.'
_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.
;
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C17(H17), C19(H19)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_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 1.421
_oxdiff_exptl_absorpt_empirical_full_min 0.803
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
S S 0.53578(5) 0.11988(4) 0.72022(3) 0.02292(12) Uani 1 1 d . . . . .
O1 O 0.34739(16) 0.12724(12) 0.70403(9) 0.0316(3) Uani 1 1 d . . . . .
O2 O 0.61256(19) 0.10390(12) 0.81070(8) 0.0334(3) Uani 1 1 d . . . . .
C1 C 1.18754(19) 0.58019(14) 0.38241(10) 0.0162(3) Uani 1 1 d . . . . .
C2 C 1.10903(19) 0.45837(14) 0.39968(10) 0.0163(3) Uani 1 1 d . . . . .
H2 H 1.121409 0.384410 0.363063 0.020 Uiso 1 1 calc R . . . .
C3 C 1.00896(19) 0.44286(14) 0.47255(9) 0.0159(3) Uani 1 1 d . . . . .
C4 C 0.92723(19) 0.31888(14) 0.49092(10) 0.0162(3) Uani 1 1 d . . . . .
H4 H 0.938052 0.244418 0.454388 0.019 Uiso 1 1 calc R . . . .
C5 C 0.83037(19) 0.30490(14) 0.56258(10) 0.0168(3) Uani 1 1 d . . . . .
C6 C 0.7351(2) 0.19725(15) 0.59838(10) 0.0183(3) Uani 1 1 d . . . . .
C7 C 0.6964(2) 0.05627(15) 0.58313(10) 0.0191(3) Uani 1 1 d . . . . .
C8 C 0.7471(2) -0.02559(15) 0.51853(11) 0.0207(3) Uani 1 1 d . . . . .
H8 H 0.817663 0.009532 0.475424 0.025 Uiso 1 1 calc R . . . .
C9 C 0.6928(2) -0.15951(15) 0.51825(12) 0.0234(3) Uani 1 1 d . . . . .
H9 H 0.726639 -0.215697 0.474352 0.028 Uiso 1 1 calc R . . . .
C10 C 0.5899(2) -0.21274(16) 0.58092(12) 0.0266(4) Uani 1 1 d . . . . .
H10 H 0.555567 -0.304569 0.579531 0.032 Uiso 1 1 calc R . . . .
C11 C 0.5365(2) -0.13319(16) 0.64566(12) 0.0259(3) Uani 1 1 d . . . . .
H11 H 0.465586 -0.168784 0.688466 0.031 Uiso 1 1 calc R . . . .
C12 C 0.5908(2) -0.00035(15) 0.64517(11) 0.0218(3) Uani 1 1 d . . . . .
C13 C 0.6601(2) 0.24633(15) 0.67188(10) 0.0188(3) Uani 1 1 d . . . . .
C14 C 0.7047(2) 0.37996(15) 0.68679(10) 0.0176(3) Uani 1 1 d . . . . .
C15 C 0.6640(2) 0.46957(14) 0.75781(10) 0.0176(3) Uani 1 1 d . . . . .
C16 C 0.7949(2) 0.51046(17) 0.83218(11) 0.0250(3) Uani 1 1 d . . . . .
C17 C 0.7590(2) 0.59859(17) 0.89701(11) 0.0271(4) Uani 1 1 d . . . . .
H17 H 0.848222 0.626903 0.947111 0.033 Uiso 1 1 calc R . . . .
C18 C 0.5968(2) 0.64691(15) 0.89111(11) 0.0235(3) Uani 1 1 d . . . . .
C19 C 0.4704(2) 0.60530(16) 0.81636(11) 0.0230(3) Uani 1 1 d . . . . .
H19 H 0.359736 0.638072 0.810381 0.028 Uiso 1 1 calc R . . . .
C20 C 0.5004(2) 0.51669(15) 0.74946(10) 0.0197(3) Uani 1 1 d . . . . .
C21 C 0.3564(2) 0.47195(18) 0.67124(12) 0.0282(4) Uani 1 1 d . . . . .
H21A H 0.410531 0.468372 0.616019 0.042 Uiso 1 1 calc GR . . . .
H21B H 0.269939 0.533280 0.666085 0.042 Uiso 1 1 calc GR . . . .
H21C H 0.294813 0.385051 0.680671 0.042 Uiso 1 1 calc GR . . . .
C22 C 0.9694(3) 0.4571(3) 0.84385(14) 0.0443(5) Uani 1 1 d . . . . .
H22A H 0.945049 0.361962 0.844715 0.066 Uiso 1 1 calc GR . . . .
H22B H 1.041541 0.493855 0.900500 0.066 Uiso 1 1 calc GR . . . .
H22C H 1.034977 0.480918 0.793915 0.066 Uiso 1 1 calc GR . . . .
C23 C 0.5650(3) 0.74253(17) 0.96586(12) 0.0300(4) Uani 1 1 d . . . . .
C24 C 0.6864(4) 0.8728(2) 0.96210(16) 0.0561(7) Uani 1 1 d . . . . .
H24A H 0.811733 0.858767 0.968754 0.084 Uiso 1 1 calc GR . . . .
H24B H 0.670035 0.933472 1.010813 0.084 Uiso 1 1 calc GR . . . .
H24C H 0.655181 0.909396 0.904324 0.084 Uiso 1 1 calc GR . . . .
C25 C 0.3710(4) 0.7656(3) 0.95685(19) 0.0712(9) Uani 1 1 d . . . . .
H25A H 0.338940 0.802583 0.899295 0.107 Uiso 1 1 calc GR . . . .
H25B H 0.356622 0.826450 1.005917 0.107 Uiso 1 1 calc GR . . . .
H25C H 0.292600 0.682632 0.959550 0.107 Uiso 1 1 calc GR . . . .
C26 C 0.6132(3) 0.69090(19) 1.05753(12) 0.0382(5) Uani 1 1 d . . . . .
H26A H 0.539633 0.606072 1.060899 0.057 Uiso 1 1 calc GR . . . .
H26B H 0.590932 0.752366 1.104366 0.057 Uiso 1 1 calc GR . . . .
H26C H 0.740169 0.681025 1.066316 0.057 Uiso 1 1 calc GR . . . .
N N 1.1037(3) -0.1871(2) 0.72508(15) 0.0631(6) Uani 1 1 d . . . . .
C27 C 1.0235(3) 0.0215(3) 0.7999(2) 0.0628(7) Uani 1 1 d . . . . .
H27A H 1.023601 0.089603 0.756958 0.094 Uiso 1 1 calc GR . . . .
H27B H 1.113226 0.051312 0.852410 0.094 Uiso 1 1 calc GR . . . .
H27C H 0.904761 0.002904 0.818683 0.094 Uiso 1 1 calc GR . . . .
C28 C 1.0667(3) -0.0969(2) 0.75752(14) 0.0457(5) Uani 1 1 d . . . . .
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 5 1 0.0279
-3 -2 8 0.0469
4 -1 -7 0.0178
-4 4 4 0.0241
-1 6 -4 0.0367
-4 -1 -4 0.0354
4 1 4 0.0320
4 -4 -3 0.0241
-1 -1 -9 0.0106
2 0 9 0.0306
-1 -2 10 0.0373
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
O1 S C12 110.71(8) . . ?
O1 S C13 111.19(7) . . ?
O2 S O1 117.38(8) . . ?
O2 S C12 110.45(8) . . ?
O2 S C13 112.20(8) . . ?
C13 S C12 92.09(7) . . ?
C2 C1 C5 121.03(13) . 2_766 ?
C2 C1 C14 129.89(13) . 2_766 ?
C14 C1 C5 109.08(13) 2_766 2_766 ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.86(13) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C3 119.21(16) . 2_766 ?
C4 C3 C2 120.56(13) . . ?
C4 C3 C3 120.23(16) . 2_766 ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.02(13) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C1 119.64(13) . 2_766 ?
C4 C5 C6 133.99(14) . . ?
C6 C5 C1 106.36(12) . 2_766 ?
C5 C6 C7 138.95(14) . . ?
C5 C6 C13 107.31(13) . . ?
C13 C6 C7 113.73(13) . . ?
C8 C7 C6 130.03(14) . . ?
C8 C7 C12 118.42(14) . . ?
C12 C7 C6 111.55(13) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 118.94(15) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.36(15) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.83(15) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 121.3 . . ?
C12 C11 C10 117.34(15) . . ?
C12 C11 H11 121.3 . . ?
C7 C12 S 111.70(11) . . ?
C11 C12 S 125.18(13) . . ?
C11 C12 C7 123.11(15) . . ?
C6 C13 S 110.88(11) . . ?
C14 C13 S 136.76(12) . . ?
C14 C13 C6 112.36(13) . . ?
C1 C14 C15 124.57(13) 2_766 . ?
C13 C14 C1 104.88(13) . 2_766 ?
C13 C14 C15 130.52(14) . . ?
C16 C15 C14 118.98(13) . . ?
C20 C15 C14 120.74(14) . . ?
C20 C15 C16 120.24(14) . . ?
C15 C16 C22 120.93(15) . . ?
C17 C16 C15 118.87(15) . . ?
C17 C16 C22 120.17(16) . . ?
C16 C17 H17 118.8 . . ?
C16 C17 C18 122.40(16) . . ?
C18 C17 H17 118.8 . . ?
C17 C18 C23 119.68(15) . . ?
C19 C18 C17 117.37(14) . . ?
C19 C18 C23 122.96(15) . . ?
C18 C19 H19 118.9 . . ?
C18 C19 C20 122.27(15) . . ?
C20 C19 H19 118.9 . . ?
C15 C20 C19 118.84(15) . . ?
C15 C20 C21 121.19(14) . . ?
C19 C20 C21 119.96(14) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C18 108.88(16) . . ?
C25 C23 C18 112.19(16) . . ?
C25 C23 C24 109.1(2) . . ?
C25 C23 C26 108.20(19) . . ?
C26 C23 C18 110.47(14) . . ?
C26 C23 C24 107.95(18) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C28 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
C28 C27 H27C 109.5 . . ?
N C28 C27 178.6(2) . . ?
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
S O1 1.4379(13) . ?
S O2 1.4367(13) . ?
S C12 1.7821(16) . ?
S C13 1.7495(16) . ?
C1 C2 1.370(2) . ?
C1 C5 1.457(2) 2_766 ?
C1 C14 1.451(2) 2_766 ?
C2 H2 0.9500 . ?
C2 C3 1.422(2) . ?
C3 C3 1.451(3) 2_766 ?
C3 C4 1.402(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(2) . ?
C5 C6 1.411(2) . ?
C6 C7 1.453(2) . ?
C6 C13 1.422(2) . ?
C7 C8 1.396(2) . ?
C7 C12 1.408(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.392(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.391(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(2) . ?
C13 C14 1.381(2) . ?
C14 C15 1.482(2) . ?
C15 C16 1.401(2) . ?
C15 C20 1.398(2) . ?
C16 C17 1.392(2) . ?
C16 C22 1.507(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.395(2) . ?
C18 C19 1.388(2) . ?
C18 C23 1.537(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.400(2) . ?
C20 C21 1.504(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.531(3) . ?
C23 C25 1.522(3) . ?
C23 C26 1.523(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N C28 1.127(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C27 C28 1.462(4) . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.5172 5.3623 1.3477 -0.2664 0.0646 -0.9617
-3.0679 -1.8338 7.7661 0.8414 -0.2017 -0.5014
3.9061 -0.5165 -7.0019 -0.6010 0.1438 0.7862
-4.0804 3.9438 3.8685 0.0664 -0.0153 -0.9977
-1.1695 6.1790 -4.0016 -0.8136 0.1957 -0.5476
-3.8664 -0.8459 -4.3747 0.2188 0.9116 -0.3479
3.9750 0.6538 4.1647 -0.2155 -0.8976 0.3845
4.0807 -4.1938 -3.2241 -0.0067 -0.0288 0.9996
-0.5989 -0.9483 -9.2186 -0.2746 0.9273 0.2544
1.7086 -0.1811 8.6063 0.2840 -0.9588 0.0090
-0.7784 -1.5471 9.6024 0.7012 -0.6652 -0.2567
