Intramolecular Nicholas Reactions in the Synthesis of Heteroenediynes fused to Indole, Triazole and Isocoumarin.
Danilkina, Natalia A.; D'yachenko, Alexander; Govdi, Anastasia I.; Khlebnikov, Alexander F.; Kornyakov, Ilya; Bräse, Stefan; Balova, Irina A.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00930

data_4038525
_publ_section_title
;
 Intramolecular Nicholas Reactions in the Synthesis of Heteroenediynes
 fused to Indole, Triazole and Isocoumarin.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00930
_journal_year                    2020
_chemical_formula_moiety         'C13 H9 I3 O3'
_chemical_formula_sum            'C13 H9 I3 O3'
_chemical_formula_weight         593.90
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-02-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.693(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6940(6)
_cell_length_b                   20.9333(14)
_cell_length_c                   9.0103(8)
_cell_measurement_reflns_used    3977
_cell_measurement_temperature    100(3)
_cell_measurement_theta_max      71.6070
_cell_measurement_theta_min      4.1590
_cell_volume                     1570.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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_temperature      100(3)
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -96.00 -67.00   0.50    0.84    --  -41.35 -60.00 170.00   58
  2  \w     17.00  58.00   0.50    0.84    --   41.35 -60.00 170.00   82
  3  \w     30.00  57.00   0.50    0.84    --   41.35  60.00 -50.00   54
  4  \w     63.00 104.00   0.50    0.84    --   41.35  60.00 -50.00   82
  5  \w     43.00 120.00   0.50    3.34    --  101.00 -60.00 170.00  154
  6  \w    106.00 151.00   0.50    3.34    --  101.00  60.00 -50.00   90
  7  \w   -100.00 -47.00   0.50    0.84    --  -41.35 -32.00-180.00  106
  8  \w    -47.00 -17.00   0.50    0.84    --  -41.35  60.00 -50.00   60
  9  \w    -22.00   4.00   0.50    0.84    --  -41.35  43.00  60.00   52
 10  \w    -48.00  22.00   0.50    0.84    --  -41.35  21.00 150.00  140
 11  \w    -50.00 -25.00   0.50    0.84    --  -41.35 -60.00 170.00   50
 12  \w     29.00  54.00   0.50    0.84    --   41.35-138.00-120.00   50
 13  \w     30.00  57.00   0.50    0.84    --   41.35 -54.00 -90.00   54
 14  \w     29.00  54.00   0.50    0.84    --   41.35 -77.00  90.00   50
 15  \w     13.00  92.00   0.50    0.84    --   41.35-138.00-180.00  158
 16  \w    -19.00  13.00   0.50    0.84    --   41.35 -54.00 -90.00   64
 17  \w     -1.00  24.00   0.50    0.84    --   41.35 -77.00  90.00   50
 18  \w     61.00  95.00   0.50    0.84    --   41.35-138.00-120.00   68
 19  \w     93.00 119.00   0.50    3.34    --  101.00  25.00-180.00   52
 20  \w     65.00  91.00   0.50    3.34    --  101.00 -33.00 150.00   52
 21  \w     39.00 117.00   0.50    3.34    --  101.00 -50.00 -60.00  156
 22  \w     78.00 105.00   0.50    3.34    --  101.00 -96.00  90.00   54
 23  \w     72.00 110.00   0.50    3.34    --  101.00 -33.00-150.00   76
 24  \w     93.00 150.00   0.50    3.34    --  101.00  25.00 -90.00  114
 25  \w     49.00  88.00   0.50    3.34    --  101.00 -25.00 -30.00   78
 26  \w     88.00 154.00   0.50    3.34    --  101.00  42.00  30.00  132
 27  \w     36.00  61.00   0.50    3.34    --  101.00 -33.00-150.00   50
 28  \w    131.00 157.00   0.50    3.34    --  101.00  50.00   0.00   52
 29  \w    119.00 152.00   0.50    3.34    --  101.00  96.00-150.00   66
 30  \w     78.00 103.00   0.50    3.34    --  101.00 -25.00 120.00   50
 31  \w     95.00 146.00   0.50    3.34    --  101.00  96.00  60.00  102
 32  \w     36.00  62.00   0.50    3.34    --  101.00 -33.00 150.00   52
 33  \w    124.00 156.00   0.50    3.34    --  101.00  25.00-180.00   64
 34  \w     57.00 113.00   0.50    3.34    --  101.00 -68.00 -30.00  112
 35  \w     33.00  62.00   0.50    3.34    --  101.00 -25.00 120.00   58
 36  \w    109.00 134.00   0.50    3.34    --  101.00  33.00-150.00   50
 37  \w     85.00 115.00   0.50    3.34    --  101.00  50.00   0.00   60
 38  \w     83.00 103.00   0.50    3.34    --  101.00  60.00 -50.00   40
;
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8320
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.916
_diffrn_reflns_theta_min         4.224
_exptl_absorpt_coefficient_mu    46.905
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.511
_exptl_crystal_description       prism
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.946
_refine_diff_density_min         -1.525
_refine_diff_density_rms         0.233
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0733P)^2^+4.0893P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1196
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2621
_reflns_number_total             2956
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00930_si_002.cif
_cod_data_source_block           dan55
_cod_database_code               4038525
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.089
_shelx_estimated_absorpt_t_min   0.027
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              76411
_shelx_hkl_checksum              70970
_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
;