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_4033624
_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_absolute_configuration unk
_chemical_formula_moiety         'C31 H20 O2'
_chemical_formula_sum            'C31 H20 O2'
_chemical_formula_weight         424.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_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                 100.440(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.0337(5)
_cell_length_b                   5.7858(3)
_cell_length_c                   19.3039(10)
_cell_measurement_reflns_used    5828
_cell_measurement_temperature    123
_cell_measurement_theta_max      30.2630
_cell_measurement_theta_min      2.6860
_cell_volume                     1102.10(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.777
_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    -21.00  19.00   0.50   14.59    --    5.65 -34.00  97.00   80
  2  \w    -22.00  19.00   0.50   14.59    --   -5.49 -99.00  60.00   82
  3  \w    -26.00  27.00   0.50   14.59    --    5.65 -99.00 -60.00  106
  4  \w    -62.00 -24.00   0.50   14.59    --    5.65 -34.00  97.00   76
  5  \w     -6.00  63.00   0.50   14.59    --    5.65  34.00-104.00  138
;
_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      -0.0640808000
_diffrn_orient_matrix_UB_12      0.0538024000
_diffrn_orient_matrix_UB_13      -0.0019874000
_diffrn_orient_matrix_UB_21      0.0077740000
_diffrn_orient_matrix_UB_22      -0.0036321000
_diffrn_orient_matrix_UB_23      0.0372794000
_diffrn_orient_matrix_UB_31      0.0315632000
_diffrn_orient_matrix_UB_32      0.1100193000
_diffrn_orient_matrix_UB_33      0.0022009000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.777
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9535
_diffrn_reflns_point_group_measured_fraction_full 0.861
_diffrn_reflns_point_group_measured_fraction_max 0.614
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.045
_diffrn_reflns_theta_min         2.064
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11387
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       prism
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1274 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4347
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0422P)^2^+0.0683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0894
_reflns_Friedel_coverage         0.579
_reflns_Friedel_fraction_full    0.722
_reflns_Friedel_fraction_max     0.451
_reflns_number_gt                3805
_reflns_number_total             4347
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02186_si_002.cif
_cod_data_source_block           8
_cod_depositor_comments
'Adding full bibliography for 4033619--4033624.cif.'
_cod_database_code               4033624
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C31 H20 O2'
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C24(H24), C18(H18), C8(H8), C14(H14), C17(H17), C29(H29), C28(H28),
 C32(H32), C31(H31), C16(H16), C11(H11), C15(H15), C10(H10), C23(H23), C9(H9),
 C20(H20), C30(H30), C22(H22), C21(H21)
;
_shelx_res_checksum              57886
_shelx_hkl_checksum              45482
_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 7.350
_oxdiff_exptl_absorpt_empirical_full_min 0.478