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_4038527
_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         'C14 H14 I N3 O2'
_chemical_formula_sum            'C14 H14 I N3 O2'
_chemical_formula_weight         383.18
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-09-25
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                97.581(2)
_cell_angle_beta                 106.756(3)
_cell_angle_gamma                103.036(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2353(3)
_cell_length_b                   9.1711(3)
_cell_length_c                   12.0759(3)
_cell_measurement_reflns_used    7809
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.1910
_cell_measurement_theta_min      3.2320
_cell_volume                     730.66(5)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
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_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -99.00  -73.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -      -23.3621  178.0000    0.0000 26

  2 omega  -57.00    7.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -      -23.3621  -77.0000  -30.0000 64

  3 omega   19.00   66.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -       24.2996  -99.0000 -150.0000 47

  4 omega  -21.00   56.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -       24.2996  -99.0000  -60.0000 77

  5 omega  -43.00   42.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -       24.2996  -57.0000   60.0000 85

  6 omega  -47.00   61.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -       24.2996  -19.0000  120.0000 108

  7 omega  -93.00    7.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -      -23.3621  -77.0000   90.0000 100

  8 omega  -82.00    5.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -      -23.3621  -77.0000 -150.0000 87

  9 omega   33.00   88.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -       24.2996   57.0000  -60.0000 55

 10 omega    5.00   66.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -       24.2996  -99.0000   30.0000 61

 11 omega   -5.00   84.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -       24.2996    0.0000 -120.0000 89
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
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_diffrn_orient_matrix_UB_11      -0.1038820000
_diffrn_orient_matrix_UB_12      -0.0230937000
_diffrn_orient_matrix_UB_13      -0.0071686000
_diffrn_orient_matrix_UB_21      0.0044305000
_diffrn_orient_matrix_UB_22      0.0765408000
_diffrn_orient_matrix_UB_23      0.0227417000
_diffrn_orient_matrix_UB_31      -0.0233816000
_diffrn_orient_matrix_UB_32      0.0143000000
_diffrn_orient_matrix_UB_33      -0.0580494000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11812
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.629
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.196
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84308
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.421
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_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3354
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0192
_refine_ls_R_factor_gt           0.0175
_refine_ls_shift/su_max          0.002
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0149P)^2^+0.3347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0402
_refine_ls_wR_factor_ref         0.0410
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3189
_reflns_number_total             3354
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00930_si_004.cif
_cod_data_source_block           5699-9923_gai-825
_cod_original_cell_volume        730.65(4)
_cod_database_code               4038527
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C14 H14 I N3 O2'
_shelx_estimated_absorpt_t_max   0.668
_shelx_estimated_absorpt_t_min   0.474
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_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:
 C8(H8A,H8B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C19(H19), C14(H14), C20(H20)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C10(H10A,H10B,H10C)
;
_olex2_submission_special_instructions 'No special instructions were received'