Regioselective Synthesis of 5-Metalated 2-Pyrones by Intramolecular Oxymetalation of Carbonyl-ene-yne Compounds Using Indium Trihalide.
Yata, Tetsuji; Kita, Yuji; Nishimoto, Yoshihiro; Yasuda, Makoto; The Journal of organic chemistry 84 (2019) 14330–14341; doi:10.1021/acs.joc.9b02186

data_4033620
_publ_section_title
;
 Regioselective Synthesis of 5-Metalated 2-Pyrones by Intramolecular
 Oxymetalation of Carbonyl-ene-yne Compounds Using Indium Trihalide.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14330
_journal_page_last               14341
_journal_paper_doi               10.1021/acs.joc.9b02186
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C18 H14 I6 In2 O2'
_chemical_formula_sum            'C18 H14 I6 In2 O2'
_chemical_formula_weight         1253.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-11
_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            8
_cell_length_a                   14.2500(2)
_cell_length_b                   14.3140(2)
_cell_length_c                   28.2402(4)
_cell_measurement_reflns_used    14331
_cell_measurement_temperature    123
_cell_measurement_theta_max      73.8750
_cell_measurement_theta_min      4.3600
_cell_volume                     5760.28(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (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      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.974
_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      0.00  48.00   0.50    0.89    --   42.80 -57.00  60.00   96
  2  \w     14.00  64.00   0.50    0.89    --   42.80 -57.00   0.00  100
  3  \w    -77.00 -46.00   0.50    3.54    -- -106.00  57.00 150.00   62
  4  \w   -113.00 -88.00   0.50    3.54    -- -106.00  -8.00  87.00   50
  5  \w   -117.00 -91.00   0.50    3.54    -- -106.00  57.00 150.00   52
  6  \w   -128.00 -96.00   0.50    3.54    -- -106.00  77.00  60.00   64
  7  \w    -62.00 -36.00   0.50    3.54    -- -106.00 125.00  30.00   52
  8  \w   -110.00 -84.00   0.50    3.54    -- -106.00 125.00 -60.00   52
  9  \w   -137.00 -69.00   0.50    3.54    -- -106.00  82.00-133.32  136
 10  \w   -111.00 -79.00   0.50    3.54    -- -106.00  37.00-180.00   64
 11  \w   -119.00 -78.00   0.50    3.54    -- -106.00  57.00-150.00   82
 12  \w   -114.00 -70.00   0.50    3.54    -- -106.00 125.00-150.00   88
 13  \w   -129.00 -65.00   0.50    3.54    -- -106.00  19.00-180.00  128
 14  \w   -140.00-115.00   0.50    3.54    -- -106.00 -57.00 -60.00   50
 15  \w   -129.00-104.00   0.50    3.54    -- -106.00-127.00-100.00   50
 16  \w   -171.00 -84.00   0.50    3.54    -- -106.00 -37.00  30.00  174
 17  \w   -142.00 -82.00   0.50    3.54    -- -106.00 -86.00 104.94  120
 18  \w   -115.00 -59.00   0.50    0.89    --  -42.80-143.00  90.00  112
 19  \w   -121.00 -87.00   0.50    3.54    -- -106.00 125.00  30.00   68
 20  \w   -123.00 -97.00   0.50    3.54    -- -106.00  77.00  30.00   52
 21  \w   -143.00 -88.00   0.50    3.54    -- -106.00 -57.00  60.00  110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0951377000
_diffrn_orient_matrix_UB_12      -0.0495541000
_diffrn_orient_matrix_UB_13      -0.0058929000
_diffrn_orient_matrix_UB_21      -0.0504322000
_diffrn_orient_matrix_UB_22      0.0952905000
_diffrn_orient_matrix_UB_23      0.0005837000
_diffrn_orient_matrix_UB_31      0.0097568000
_diffrn_orient_matrix_UB_32      0.0065409000
_diffrn_orient_matrix_UB_33      -0.0542360000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1020
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            30258
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.209
_diffrn_reflns_theta_min         4.408
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    63.391
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.31d (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    2.890
_exptl_crystal_description       prism
_exptl_crystal_F_000             4432
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.795
_refine_diff_density_min         -1.792
_refine_diff_density_rms         0.356
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         5710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0496
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1343
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5341
_reflns_number_total             5710
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02186_si_002.cif
_cod_data_source_block           4b
_cod_depositor_comments
'Adding full bibliography for 4033619--4033624.cif.'
_cod_database_code               4033620
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C16 H13 O2 In2 I6'
_reflns_odcompleteness_completeness 96.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00J), C00K(H00K),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R)
2.b Idealised Me refined as rotating group:
 C00S(H00A,H00B,H00D)
;
_shelx_res_checksum              27422
_shelx_hkl_checksum              65490
_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 3.398
_oxdiff_exptl_absorpt_empirical_full_min 0.373