An asymmetric organocatalytic vinylogous Mannich reaction of 3-methyl-5-arylfuran-2(3H)-ones with N-(2-pyridinesulfonyl) imines: enantioselective synthesis of δ-amino γ,γ-disubstituted butenolides.
Wang, Zhen-Hua; You, Yong; Chen, Yong-Zheng; Xu, Xiao-Ying; Yuan, Wei-Cheng; Organic & biomolecular chemistry 16 (2018) 1636–1640; doi:10.1039/c7ob03117c

data_7156127
_publ_section_title
;
 An asymmetric organocatalytic vinylogous Mannich reaction of
 3-methyl-5-arylfuran-2(3H)-ones with N-(2-pyridinesulfonyl) imines:
 enantioselective synthesis of \d-amino \g,\g-disubstituted butenolides.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1636
_journal_page_last               1640
_journal_paper_doi               10.1039/c7ob03117c
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety
'3(C23 H20 N2 O4 S), C H4 O, C23 H21.2 N2 O4.6 S, 1.4(H2 O1)'
_chemical_formula_sum            'C93 H88 N8 O19 S4'
_chemical_formula_weight         1749.95
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-02-03
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-02-03 deposited with the CCDC.
2018-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                81.909(3)
_cell_angle_beta                 88.938(3)
_cell_angle_gamma                72.873(3)
_cell_formula_units_Z            1
_cell_length_a                   11.3575(4)
_cell_length_b                   12.9479(6)
_cell_length_c                   15.7889(5)
_cell_measurement_reflns_used    10576
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5340
_cell_measurement_theta_min      4.0650
_cell_volume                     2196.15(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    '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(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -58.00  -31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -30.0000 27

  2 omega  -26.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -30.0000 45

  3 omega  -30.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -120.0000 45

  4 omega  -68.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -120.0000 34

  5 omega  -53.00  -12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -64.0000  119.3491 41

  6 omega  -87.00  -60.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -64.0000  119.3491 27

  7 omega  -80.00  -12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  111.0000  -60.0000 68

  8 omega  -70.00  -39.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000    0.0000 31

  9 omega -108.00  -82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000    0.0000 26

 10 omega   -3.00   22.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   97.0000  -51.8230 25

 11 omega   11.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -111.0000 -154.0000 68

 12 omega   77.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 32

 13 omega   59.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 36

 14 omega   -4.00   61.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -90.0000 65

 15 omega    0.00   25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.0000   98.0000 -128.3021 25

 16 omega    8.00   33.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   90.0000   76.8588 25

 17 omega    8.00   35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   90.0000    0.4123 27

 18 omega    7.00   32.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   92.0000  162.8593 25

 19 omega   13.00   38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   88.0000  -69.4585 25

 20 omega   20.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   84.0000  -72.7837 25

 21 omega   20.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   84.0000  -20.3637 25

 22 omega   20.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   84.0000  119.2121 25

 23 omega   20.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   83.0000 -117.7914 25

 24 omega   22.00   47.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   80.0000 -158.0757 25

 25 omega   20.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   83.0000   28.4399 25

 26 omega   21.00   46.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   82.0000   64.1280 25

 27 omega   95.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000  166.1338 29

 28 omega   27.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000  166.1338 36

 29 omega   34.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000 -119.0011 75

 30 omega   83.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000   39.1981 32

 31 omega   27.00   77.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000   39.1981 50

 32 omega   90.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   70.0000  132.1911 37

 33 omega   32.00  128.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   75.0000   92.3656 96

 34 omega   75.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   72.0000    2.0539 51

 35 omega   34.00   59.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   72.0000 -156.5597 25

 36 omega   39.00   75.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   70.0000  132.1911 36

 37 omega   36.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   72.0000    2.0539 28

 38 omega   32.00  128.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   75.0000  -53.7193 96

 39 omega   49.00   87.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   48.0000   26.2321 38

 40 omega  103.00  138.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   79.0000 -162.8516 35

 41 omega   42.00   87.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   79.0000 -162.8516 45

 42 omega  109.00  176.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 67

 43 omega   88.00  114.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -120.0000 26

 44 omega   79.00  104.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 25

 45 omega   79.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 26

 46 omega   88.00  176.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 88

 47 omega   88.00  114.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 26

 48 omega   79.00  171.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 92

 49 omega   38.00   76.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 38

 50 omega  112.00  173.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 61

 51 omega   79.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 26

 52 omega   41.00  135.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 94

 53 omega   88.00  114.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 26

 54 omega   38.00   84.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 46

 55 omega   79.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 26

 56 omega  121.00  167.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 46

 57 omega   79.00  168.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 89

 58 omega   88.00  114.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 26

 59 omega   88.00  114.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 26

 60 omega   88.00  115.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 27

 61 omega   88.00  114.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 26

 62 omega   79.00  176.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 97

 63 omega   79.00  162.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 83

 64 omega   50.00  115.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 65

 65 omega   79.00  174.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 95

 66 omega   79.00  168.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 89

 67 omega   46.00  104.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 58

 68 omega   79.00  157.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 78

 69 omega   54.00  109.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 55

 70 omega  111.00  172.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 61

 71 omega   79.00  104.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1339600000
_diffrn_orient_matrix_UB_12      0.0223815000
_diffrn_orient_matrix_UB_13      0.0298667000
_diffrn_orient_matrix_UB_21      0.0470250000
_diffrn_orient_matrix_UB_22      -0.0511418000
_diffrn_orient_matrix_UB_23      0.0917665000
_diffrn_orient_matrix_UB_31      0.0012219000
_diffrn_orient_matrix_UB_32      0.1127022000
_diffrn_orient_matrix_UB_33      0.0201334000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31604
_diffrn_reflns_point_group_measured_fraction_full 0.911
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.608
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83268
_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    1.323
_exptl_crystal_description       prism
_exptl_crystal_F_000             918
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 4989 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1204
_refine_ls_number_reflns         14303
_refine_ls_number_restraints     111
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0458
_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/[\s^2^(Fo^2^)+(0.0618P)^2^+0.3041P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1208
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    0.824
_reflns_Friedel_fraction_max     0.824
_reflns_number_gt                12828
_reflns_number_total             14303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob03117c2.cif
_cod_data_source_block           20180149a
_cod_depositor_comments          'Adding full bibliography for 7156127.cif.'
_cod_original_cell_volume        2196.14(15)
_cod_database_code               7156127
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H30N3O5S1Br1
_shelx_estimated_absorpt_t_max   0.794
_shelx_estimated_absorpt_t_min   0.698
_reflns_odcompleteness_completeness 99.90
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C22B) \\sim Ueq, Uanis(C22E) \\sim Ueq, Uanis(C23E) \\sim Ueq,
Uanis(C23B) \\sim Ueq, Uanis(C20E) \\sim Ueq, Uanis(C20B) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C23F) \\sim Ueq, Uanis(C23D) \\sim Ueq, Uanis(N2C) \\sim Ueq, Uanis(N2E)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C23F) \\sim Ueq, Uanis(C23D) \\sim Ueq, Uanis(C21F) \\sim Ueq,
Uanis(C21D) \\sim Ueq, Uanis(C20F) \\sim Ueq, Uanis(C20D) \\sim Ueq,
Uanis(C19D) \\sim Ueq, Uanis(C19F) \\sim Ueq, Uanis(C22D) \\sim Ueq,
Uanis(C22F) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(S1B) = Uanis(S1D)
Uanis(O3B) = Uanis(O3D)
Uanis(O4B) = Uanis(O4D)
Uanis(N1B) = Uanis(N1D)
Uanis(S1C) = Uanis(S1E)
Uanis(O3C) = Uanis(O3E)
Uanis(O4C) = Uanis(O4E)
Uanis(C20B) = Uanis(C20E)
Uanis(C21B) = Uanis(C21E)
Uanis(C22B) = Uanis(C22E)
Uanis(N3) = Uanis(N2D)
Uanis(C23B) = Uanis(C23E)
Uanis(C19D) = Uanis(C19F)
Uanis(C20D) = Uanis(C20F)
Uanis(C21D) = Uanis(C21F)
Uanis(C23D) = Uanis(C23F)
Uanis(C22D) = Uanis(C22F)
Uanis(N2C) = Uanis(N2E)
Uanis(C11B) = Uanis(C11D)
Uanis(N1C) = Uanis(N1E)
Uanis(C11C) = Uanis(C11E)
Uanis(O6) = Uanis(O6A)
Uanis(O7) = Uanis(O7A)
3. Others
 Sof(C11D)=Sof(H11D)=Sof(N1D)=Sof(H1D)=Sof(O3D)=Sof(O4D)=Sof(S1D)=1-FVAR(1)
 Sof(C11B)=Sof(H11B)=Sof(N1B)=Sof(H1B)=Sof(O3B)=Sof(O4B)=Sof(S1B)=FVAR(1)
 Sof(C11E)=Sof(H11E)=Sof(N1E)=Sof(H1E)=Sof(O3E)=Sof(O4E)=Sof(S1E)=1-FVAR(2)
 Sof(C11C)=Sof(H11C)=Sof(N1C)=Sof(H1C)=Sof(O3C)=Sof(O4C)=Sof(S1C)=FVAR(2)
 Sof(C19E)=Sof(C20E)=Sof(H20E)=Sof(C21E)=Sof(H21E)=Sof(C22E)=Sof(H22E)=
 Sof(C23E)=Sof(H23E)=Sof(N2D)=1-FVAR(3)
 Sof(C19B)=Sof(C20B)=Sof(H20B)=Sof(C21B)=Sof(H21B)=Sof(C22B)=Sof(H22B)=
 Sof(C23B)=Sof(H23B)=Sof(N3)=FVAR(3)
 Sof(C19F)=Sof(C20F)=Sof(H20F)=Sof(C21F)=Sof(H21F)=Sof(C22F)=Sof(H22F)=
 Sof(C23F)=Sof(H23F)=Sof(N2E)=1-FVAR(4)
 Sof(C19D)=Sof(C20D)=Sof(H20D)=Sof(C21D)=Sof(H21D)=Sof(C22D)=Sof(H22D)=
 Sof(C23D)=Sof(H23D)=Sof(N2C)=FVAR(4)
 Sof(O6A)=Sof(H6AA)=Sof(H6AB)=Sof(O7A)=Sof(H7AB)=Sof(H7AA)=1-FVAR(5)
 Sof(O6)=Sof(H6D)=Sof(H6E)=Sof(O7)=Sof(H7D)=Sof(H7E)=FVAR(5)
4.a Riding coordinates:
 O5(H5), O6(H6D,H6E), O6A(H6AA,H6AB), O7A(H7AB,H7AA)
4.b Free rotating group:
 O7(H7D,H7E)
4.c Ternary CH refined with riding coordinates:
 C11(H11), C11A(H11A), C11B(H11B), C11C(H11C), C11D(H11D), C11E(H11E)
4.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C3A(H3A),
  C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A), C10A(H10A), C13A(H13A), C14A(H14A),
 C15A(H15A), C16A(H16A), C17A(H17A), C20A(H20A), C21A(H21A), C22A(H22A),
 C23A(H23A), C3B(H3B), C3C(H3C), C6B(H6B), C6C(H6C), C7B(H7B), C7C(H7C),
 C8B(H8B), C8C(H8C), C9B(H9B), C9C(H9C), C10B(H10B), C10C(H10C), C13B(H13B),
 C13C(H13C), C14B(H14B), C14C(H14C), C15B(H15B), C15C(H15C), C16B(H16B),
 C16C(H16C), C17B(H17B), C17C(H17C), C20F(H20F), C21F(H21F), C22F(H22F),
 C23F(H23F), C20B(H20B), C20D(H20D), C20E(H20E), C21B(H21B), C21D(H21D),
 C21E(H21E), C22B(H22B), C22D(H22D), C22E(H22E), C23B(H23B), C23D(H23D),
 C23E(H23E), N1B(H1B), N1C(H1C), N1D(H1D), N1E(H1E)
4.e Fitted hexagon refined as free rotating group:
 C19F(C20F,C21F,C22F,C23F,N2E)
4.f Idealised Me refined as rotating group:
 C18(H18G,H18H,H18I), C18A(H18J,H18K,H18L), C24(H24B,H24C,H24A), C18B(H18A,
 H18B,H18C), C18C(H18D,H18E,H18F)
;
_olex2_submission_special_instructions 'No special instructions were received'