Atropisomerism in a 10-Membered Ring with Multiple Chirality Axes: (3 Z,9 Z)-1,2,5,8-Dithiadiazecine-6,7(5 H,8 H)-dione Series.
Risso, Vesna; Farran, Daniel; Javierre, Guilhem; Naubron, Jean-Valère; Giorgi, Michel; Piras, Patrick; Jean, Marion; Vanthuyne, Nicolas; Fruttero, Roberta; Lorcy, Dominique; Roussel, Christian; The Journal of organic chemistry 83 (2018) 7566–7573; doi:10.1021/acs.joc.8b01009

data_4035585
_publ_section_title
;
 Atropisomerism in a 10-Membered Ring with Multiple Chirality Axes: (3 Z,9
 Z)-1,2,5,8-Dithiadiazecine-6,7(5 H,8 H)-dione Series.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7566
_journal_page_last               7573
_journal_paper_doi               10.1021/acs.joc.8b01009
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C20 H18 N2 O2 S2'
_chemical_formula_sum            'C20 H18 N2 O2 S2'
_chemical_formula_weight         382.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-26
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.1778(17)
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_cell_length_c                   17.5366(10)
_cell_measurement_reflns_used    11858
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.2830
_cell_measurement_theta_min      4.0690
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_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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;
  1 omega  -41.00    1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega  -35.00   -1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega    1.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.3416  -99.0000    0.0000 61

  4 omega   55.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.3416 -178.0000  -30.0000 70

  5 omega   47.00  116.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077 -111.0000  -60.0000 69

  6 omega   37.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega   83.00  143.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   63.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega   24.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077  -77.0000  120.0000 46

 10 omega  104.00  130.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   49.0000   16.8982 26

 11 omega  114.00  164.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   72.0000   53.3666 50

 12 omega  126.00  177.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077  111.0000   90.0000 51

 13 omega  132.00  158.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   50.0000  -44.1065 26

 14 omega  112.00  150.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       94.0000   77.0000 -159.1766 38

 15 omega   85.00  131.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 16 omega   67.00  137.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077   61.0000 -120.0000 70

 17 omega   97.00  171.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077   77.0000  -30.0000 74

 18 omega   65.00  165.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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 19 omega   65.00  150.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077   77.0000   90.0000 85

 20 omega   65.00  156.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077   77.0000  150.0000 91

 21 omega   65.00  162.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077   77.0000   30.0000 97

 22 omega   65.00  157.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077   77.0000  -90.0000 92

 23 omega   65.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077   77.0000 -120.0000 26

 24 omega   56.00   83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       94.0000   77.0000 -159.1766 27

 25 omega   65.00  172.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077   77.0000 -180.0000 107

 26 omega   65.00   94.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077   77.0000  -30.0000 29

 27 omega   65.00  174.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077   77.0000  -60.0000 109

 28 omega   65.00  174.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077   77.0000  120.0000 109

 29 omega   65.00  177.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077   77.0000   60.0000 112

 30 omega   59.00  128.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0077  178.0000 -180.0000 69

 31 omega   38.00   82.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   50.0000  -44.1065 44

 32 omega   38.00   81.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   49.0000   16.8982 43

 33 omega   40.00   77.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   72.0000   53.3666 37

 34 omega   47.00   76.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   75.0000  139.5677 29

 35 omega   22.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   78.0000  136.0390 27

 36 omega   18.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   82.0000   86.5850 27

 37 omega   18.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   82.0000   53.7238 25

 38 omega   18.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   79.0000   20.9580 25

 39 omega   18.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   81.0000  -27.1715 28

 40 omega   22.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   78.0000  -58.1213 25

 41 omega   23.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000 -109.9997 85

 42 omega   28.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   71.0000 -177.9750 44

 43 omega   19.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   82.0000 -165.1622 26

 44 omega   14.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   83.0000  -96.9577 25

 45 omega  -16.00    9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000  111.0000 -110.3735 25

 46 omega  -75.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.3416   77.0000  120.0000 130

 47 omega  -15.00   10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000  111.0000  140.2456 25

 48 omega  -96.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.3416  -57.0000    0.0000 52

 49 omega -120.00  -51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.3416  -38.0000   60.0000 69

 50 omega -120.00   -1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -35.3416  -57.0000  150.0000 119
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_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_32      -0.0181514000
_diffrn_orient_matrix_UB_33      -0.1232588000
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_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
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_diffrn_reflns_av_unetI/netI     0.0165
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_diffrn_reflns_point_group_measured_fraction_max 0.995
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_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.752
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_exptl_absorpt_correction_T_min  0.83492
_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_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1600
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1288
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3118
_reflns_number_total             3452
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01009_si_002.cif
_cod_data_source_block           vr18
_cod_original_cell_volume        3692.8(5)
_cod_database_code               4035585
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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), C3(H3), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'