Relative Reactivity of Benzothiophene-Fused Enediynes in the Bergman Cyclization.
Lyapunova, Anna G.; Danilkina, Natalia A.; Rumyantsev, Andrey M.; Khlebnikov, A. F.; Chislov, Mikhail V.; Starova, Galina L.; Sambuk, Elena V.; Govdi, Anastasia I.; Bräse, Stefan; Balova, Irina A.; The Journal of organic chemistry 83 (2018) 2788–2801; doi:10.1021/acs.joc.7b03258

data_4034956
_publ_section_title
;
 Relative Reactivity of Benzothiophene-Fused Enediynes in the Bergman
 Cyclization.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2788
_journal_page_last               2801
_journal_paper_doi               10.1021/acs.joc.7b03258
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C29 H18 Co2 O9 S'
_chemical_formula_sum            'C29 H18 Co2 O9 S'
_chemical_formula_weight         660.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-21
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.3536(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.7863(3)
_cell_length_b                   7.78776(18)
_cell_length_c                   23.6336(4)
_cell_measurement_reflns_used    13863
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.1220
_cell_measurement_theta_min      3.4830
_cell_volume                     2721.41(10)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9659
_diffrn_measured_fraction_theta_max 0.9659
_diffrn_measurement_details
;
  1 omega  -96.00  -22.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -38.0000   60.0000 74

  2 omega  -44.00   12.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000 -150.0000 56

  3 omega  104.00  130.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4354  178.0000  120.0000 26

  4 omega   38.00   86.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000    0.0000 48

  5 omega   42.00  116.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  -60.0000 74

  6 omega   85.00  175.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000   30.0000 90

  7 omega   37.00   68.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -90.0000 31

  8 omega   82.00  109.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 27

  9 omega   56.00   85.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 29

 10 omega  -49.00  -13.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -57.0000    0.0000 36

 11 omega  -70.00   32.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   57.0000  -90.0000 102

 12 omega -115.00  -13.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -57.0000  -90.0000 102

 13 omega  -50.00   33.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000   60.0000 83

 14 omega  -92.00    0.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -19.0000   90.0000 92

 15 omega   57.00  126.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4354  178.0000 -180.0000 69

 16 omega   13.00   38.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   80.0000  117.0122 25

 17 omega   17.00   42.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   79.0000  -84.1576 25

 18 omega   16.00   41.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   82.0000  136.6843 25

 19 omega   21.00   46.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000 -164.8109 25

 20 omega   20.00   45.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000 -152.6816 25

 21 omega   20.00   45.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000   92.5214 25

 22 omega   20.00   45.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000  -46.2398 25

 23 omega   20.00   45.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000   13.0357 25

 24 omega   26.00   52.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  -59.9782 26

 25 omega  102.00  129.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  -59.9782 27

 26 omega   33.00   59.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000   26.8886 26

 27 omega  116.00  141.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   74.0000  134.6427 25

 28 omega   35.00   61.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   74.0000  134.6427 26

 29 omega   34.00   60.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  -31.8247 26

 30 omega   40.00   82.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   65.0000  120.9366 42

 31 omega   37.00   81.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000 -124.6666 44

 32 omega   40.00   66.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   71.0000  175.1457 26

 33 omega   90.00  117.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000 -124.6666 27

 34 omega   37.00   64.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000 -148.6542 27

 35 omega   45.00   71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   62.0000   11.2765 26

 36 omega   45.00   71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   63.0000  -55.1519 26

 37 omega   47.00   92.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   72.0000   37.8633 45

 38 omega   50.00   76.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   73.0000   68.3959 26

 39 omega   59.00  106.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   60.0000  -43.4328 47

 40 omega   52.00   88.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   66.0000   25.0228 36

 41 omega   60.00   93.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   68.0000   88.8732 33

 42 omega   64.00   90.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       94.0000   66.0000 -134.6356 26

 43 omega   66.00   92.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   74.0000  -92.8750 26

 44 omega   67.00   93.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   71.0000  173.0785 26

 45 omega   67.00  112.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   75.0000  -77.3320 45

 46 omega  124.00  150.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      102.0000   76.0000  126.7836 26

 47 omega   72.00   97.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      102.0000   70.0000   67.7462 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0930277000
_diffrn_orient_matrix_UB_12      0.0228188000
_diffrn_orient_matrix_UB_13      0.0287407000
_diffrn_orient_matrix_UB_21      -0.0459858000
_diffrn_orient_matrix_UB_22      0.0058043000
_diffrn_orient_matrix_UB_23      0.0582871000
_diffrn_orient_matrix_UB_31      0.0095057000
_diffrn_orient_matrix_UB_32      -0.1963751000
_diffrn_orient_matrix_UB_33      0.0050619000
_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  0.0591
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            27561
_diffrn_reflns_theta_full        69.99
_diffrn_reflns_theta_max         69.99
_diffrn_reflns_theta_min         3.52
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    10.748
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31867
_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            red
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         4915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0544
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+12.1862P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.1014
_reflns_number_gt                4119
_reflns_number_total             4915
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b03258_si_001.cif
_cod_data_source_block           agl154
_cod_database_code               4034956
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 96.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97