Electrophilic cyclization of aryldiacetylenes in the synthesis of functionalized enediynes fused to a heterocyclic core.
Danilkina, N. A.; Kulyashova, A. E.; Khlebnikov, A. F.; Bräse, S; Balova, I. A.; The Journal of organic chemistry 79 (2014) 9018–9045; doi:10.1021/jo501396s

data_4029934
_publ_section_title
;
 Electrophilic cyclization of aryldiacetylenes in the synthesis of
 functionalized enediynes fused to a heterocyclic core.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9018
_journal_page_last               9045
_journal_paper_doi               10.1021/jo501396s
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C21 H19 N O2'
_chemical_formula_sum            'C21 H19 N O2'
_chemical_formula_weight         317.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-08-18
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.5810(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.6232(2)
_cell_length_b                   8.48700(10)
_cell_length_c                   24.2138(2)
_cell_measurement_reflns_used    42815
_cell_measurement_temperature    100
_cell_measurement_theta_max      76.3150
_cell_measurement_theta_min      2.8050
_cell_volume                     3218.55(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.9939
_diffrn_measured_fraction_theta_max 0.9939
_diffrn_measurement_details
;
  1 omega    0.00   25.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0000   93.0000  -47.1816 25

  2 omega    3.00   29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0000   87.0000  136.8209 26

  3 omega    3.00   28.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0000   87.0000   52.0800 25

  4 omega  -71.00   33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.1287   57.0000    0.0000 104

  5 omega  -91.00  -54.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.1287  -38.0000  120.0000 37

  6 omega -114.00  -83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.1287  -57.0000  -60.0000 31

  7 omega  -41.00  -15.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.1287  -38.0000  120.0000 26

  8 omega -115.00  -53.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.1287  -57.0000 -120.0000 62

  9 omega  -72.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.1287  -57.0000  -60.0000 60

 10 omega  -41.00  -14.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.1287  -57.0000 -120.0000 27

 11 omega -117.00  -15.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.1287  -38.0000   30.0000 102

 12 omega   24.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.1287 -126.0000  -90.0000 66

 13 omega   24.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.1287 -126.0000  120.0000 75

 14 omega   12.00   37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   84.0000  158.2363 25

 15 omega   18.00   43.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   80.0000  -85.2495 25

 16 omega   17.00   42.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   81.0000   56.2923 25

 17 omega   18.00   43.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   80.0000  -33.2662 25

 18 omega   22.00   47.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000 -140.7313 25

 19 omega   79.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   76.0000 -157.6379 58

 20 omega   30.00   56.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   76.0000 -157.6379 26

 21 omega   27.00   53.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   77.0000   96.9651 26

 22 omega   30.00   56.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000  167.1662 26

 23 omega   31.00   57.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   76.0000  -11.1222 26

 24 omega   35.00   60.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000   15.4875 25

 25 omega   80.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000   15.4875 41

 26 omega   35.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000  152.4826 48

 27 omega   38.00   66.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000   68.2425 28

 28 omega   38.00   63.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000 -129.0058 25

 29 omega  106.00  150.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000  -63.9578 44

 30 omega   40.00   66.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   75.0000  -94.4351 26

 31 omega   92.00  142.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   75.0000  -94.4351 50

 32 omega  112.00  144.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   75.0000   30.1528 32

 33 omega   39.00   66.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   75.0000   30.1528 27

 34 omega   38.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000  115.4052 61

 35 omega   38.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000  -63.9578 44

 36 omega   79.00  128.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 49

 37 omega   79.00  114.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 35

 38 omega  129.00  158.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 29

 39 omega   79.00  125.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 46

 40 omega   79.00  105.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 26

 41 omega   76.00  108.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  120.0000 32

 42 omega   36.00   73.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  120.0000 37

 43 omega  116.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 60

 44 omega   79.00  111.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 32

 45 omega   83.00  170.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -30.0000 87

 46 omega   32.00  100.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 68

 47 omega   44.00  105.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 61

 48 omega   82.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 27

 49 omega   79.00  160.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 81

 50 omega   77.00  115.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 38

 51 omega  114.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 64

 52 omega   79.00  108.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 29

 53 omega   36.00   63.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 27

 54 omega   82.00  115.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 33

 55 omega   35.00   61.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 26

 56 omega   81.00  115.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 34

 57 omega  119.00  173.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 54

 58 omega   83.00  131.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -180.0000 48

 59 omega   50.00  101.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   30.0000 51

 60 omega  124.00  170.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 46

 61 omega   79.00  129.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -90.0000 50

 62 omega  134.00  160.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -90.0000 26

 63 omega   42.00   68.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 26

 64 omega   26.00  177.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   -4.0000  -57.2708 151

 65 omega  145.00  177.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 32

 66 omega   79.00  131.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 52

 67 omega   44.00   93.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -39.0000   72.0826 49

 68 omega   30.00  101.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  120.0000 71

 69 omega   79.00  105.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 26

 70 omega  132.00  177.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 45

 71 omega   83.00  127.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 44

 72 omega  147.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 31

 73 omega   86.00  161.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 75

 74 omega   73.00  115.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 42

 75 omega   79.00  138.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 59

 76 omega   35.00   61.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 26

 77 omega   84.00  142.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 58

 78 omega   38.00   67.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 29

 79 omega   83.00  159.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 76

 80 omega   83.00  165.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 82

 81 omega  103.00  135.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -120.0000 32

 82 omega   79.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 96

 83 omega   54.00   83.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -120.0000 29

 84 omega   37.00   62.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0260622000
_diffrn_orient_matrix_UB_12      -0.0542005000
_diffrn_orient_matrix_UB_13      0.0286708000
_diffrn_orient_matrix_UB_21      0.0467149000
_diffrn_orient_matrix_UB_22      0.0267966000
_diffrn_orient_matrix_UB_23      0.0591500000
_diffrn_orient_matrix_UB_31      -0.0825420000
_diffrn_orient_matrix_UB_32      -0.0019433000
_diffrn_orient_matrix_UB_33      0.0155372000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            70891
_diffrn_reflns_theta_full        76.68
_diffrn_reflns_theta_max         76.68
_diffrn_reflns_theta_min         2.82
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         6760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0691P)^2^+1.8429P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1303
_reflns_number_gt                6556
_reflns_number_total             6760
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501396s_si_003.cif
_cod_data_source_block           sku_83_2
_cod_depositor_comments          'Adding full bibliography for 4029934.cif.'
_cod_database_code               4029934
_chemical_oxdiff_formula         'C22 N1 O2 H30'
_reflns_odcompleteness_completeness 95.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95