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_4038526
_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         'C16 H16 I N O3'
_chemical_formula_sum            'C16 H16 I N O3'
_chemical_formula_weight         397.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2618(3)
_cell_length_b                   43.8957(17)
_cell_length_c                   4.20886(17)
_cell_measurement_reflns_used    2916
_cell_measurement_temperature    100(3)
_cell_measurement_theta_max      71.8450
_cell_measurement_theta_min      2.0630
_cell_volume                     1526.37(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.977
_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    -50.00 -25.00   0.50    0.91    --  -41.35  52.00  28.00   50
  2  \w    -76.00 -46.00   0.50    0.91    --  -41.35 -52.00-116.00   60
  3  \w     -3.00  22.00   0.50    0.91    --  -41.35  52.00  28.00   50
  4  \w     54.00  79.00   0.50    0.91    --   41.35  52.00  28.00   50
  5  \w    111.00 157.00   0.50    3.64    --  101.00  52.00  28.00   92
  6  \w     54.00  79.00   0.50    3.64    --  101.00 -52.00-116.00   50
  7  \w    -54.00 -27.00   0.50    0.91    --  -41.35 -11.00  60.00   54
  8  \w   -113.00 -67.00   0.50    0.91    --  -41.35 -11.00  60.00   92
  9  \w    -21.00   4.00   0.50    0.91    --   41.35 -65.00  90.00   50
 10  \w     48.00  91.00   0.50    0.91    --   41.35-138.00 -60.00   86
 11  \w    -14.00  24.00   0.50    0.91    --   41.35 -32.00 150.00   76
 12  \w     13.00  53.00   0.50    0.91    --   41.35 -65.00  90.00   80
 13  \w     22.00  52.00   0.50    0.91    --   41.35 -52.00-116.00   60
 14  \w     38.00  71.00   0.50    3.64    --  101.00 -42.00  90.00   66
 15  \w     90.00 120.00   0.50    3.64    --  101.00 -59.00   0.00   60
 16  \w     82.00 129.00   0.50    3.64    --  101.00   8.00 -30.00   94
 17  \w     70.00 100.00   0.50    3.64    --  101.00 -93.00  90.00   60
 18  \w     34.00  70.00   0.50    3.64    --  101.00 -17.00   0.00   72
 19  \w     78.00 107.00   0.50    3.64    --  101.00 -17.00   0.00   58
 20  \w     97.00 146.00   0.50    3.64    --  101.00  25.00-180.00   98
 21  \w     75.00 115.00   0.50    3.64    --  101.00-111.00 -90.00   80
 22  \w     41.00  72.00   0.50    3.64    --  101.00 -59.00   0.00   62
 23  \w     44.00  74.00   0.50    3.64    --  101.00 -42.00-150.00   60
 24  \w     36.00  73.00   0.50    3.64    --  101.00-111.00 -90.00   74
 25  \w     88.00 129.00   0.50    3.64    --  101.00  17.00 -90.00   82
 26  \w     33.00  64.00   0.50    3.64    --  101.00 -93.00  90.00   62
 27  \w     84.00 114.00   0.50    3.64    --  101.00-111.00  30.00   60
 28  \w     52.00 102.00   0.50    3.64    --  101.00-111.00 -30.00  100
 29  \w     39.00  83.00   0.50    3.64    --  101.00-111.00  30.00   88
 30  \w     88.00 114.00   0.50    3.64    --  101.00 -42.00  90.00   52
 31  \w     36.00  64.00   0.50    3.64    --  101.00 -33.00 -90.00   56
 32  \w     85.00 110.00   0.50    3.64    --  101.00 -33.00 -90.00   50
 33  \w    132.00 157.00   0.50    3.64    --  101.00   8.00 -30.00   50
 34  \w     66.00  93.00   0.50    3.64    --  101.00 -50.00 120.00   54
 35  \w     52.00 103.00   0.50    3.64    --  101.00-111.00-180.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0513744000
_diffrn_orient_matrix_UB_12      -0.0310823000
_diffrn_orient_matrix_UB_13      0.1366114000
_diffrn_orient_matrix_UB_21      0.1028620000
_diffrn_orient_matrix_UB_22      -0.0162821000
_diffrn_orient_matrix_UB_23      -0.2538587000
_diffrn_orient_matrix_UB_31      0.1467358000
_diffrn_orient_matrix_UB_32      0.0005576000
_diffrn_orient_matrix_UB_33      0.2257832000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       53
_diffrn_reflns_limit_k_min       -53
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            7055
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.410
_diffrn_reflns_theta_min         2.013
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    16.571
_exptl_absorpt_correction_T_max  0.509
_exptl_absorpt_correction_T_min  0.020
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.728
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.027
_exptl_crystal_size_min          0.013
_refine_diff_density_max         2.229
_refine_diff_density_min         -1.447
_refine_diff_density_rms         0.208
_refine_ls_abs_structure_details
;
 Flack x determined using 779 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2686
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0660
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0650P)^2^+22.8379P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1788
_refine_ls_wR_factor_ref         0.1819
_reflns_Friedel_coverage         0.586
_reflns_Friedel_fraction_full    0.791
_reflns_Friedel_fraction_max     0.765
_reflns_number_gt                2385
_reflns_number_total             2686
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00930_si_001.cif
_cod_data_source_block           das118
_cod_database_code               4038526
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C64  H64  I4  N4  O12  '
_reflns_odcompleteness_completeness 98.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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:
 C13(H13A,H13B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C15(H15C,H15A,H15B), C21(H21A,H21C,H21B)
;
_shelx_res_checksum              89304
_shelx_hkl_checksum              51758
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.791
_oxdiff_exptl_absorpt_empirical_full_min 0.507