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_4033621
_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         'C29 H20 O2'
_chemical_formula_sum            'C29 H20 O2'
_chemical_formula_weight         400.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                85.011(3)
_cell_angle_beta                 79.264(3)
_cell_angle_gamma                71.536(3)
_cell_formula_units_Z            4
_cell_length_a                   10.2861(4)
_cell_length_b                   12.2992(4)
_cell_length_c                   18.0217(7)
_cell_measurement_reflns_used    10174
_cell_measurement_temperature    123
_cell_measurement_theta_max      29.3280
_cell_measurement_theta_min      2.1050
_cell_volume                     2123.76(14)
_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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.785
_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    -77.00  -4.00   0.50   16.46    --   -5.42 -38.00   0.00  146
  2  \w    -71.00   8.00   0.50   16.46    --   -5.42 -38.00 -90.00  158
  3  \w     -7.00  19.00   0.50   16.46    --   -5.42 -99.00-150.00   52
  4  \w    -46.00 -11.00   0.50   16.46    --    5.49 -38.00-150.00   70
  5  \w    -78.00  -1.00   0.50   16.46    --   -5.42 -38.00  60.00  154
  6  \w    -67.00   4.00   0.50   16.46    --   -5.42 -57.00 150.00  142
;
_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      0.0584258000
_diffrn_orient_matrix_UB_12      -0.0070501000
_diffrn_orient_matrix_UB_13      -0.0292255000
_diffrn_orient_matrix_UB_21      0.0423548000
_diffrn_orient_matrix_UB_22      -0.0011075000
_diffrn_orient_matrix_UB_23      0.0271116000
_diffrn_orient_matrix_UB_31      0.0152048000
_diffrn_orient_matrix_UB_32      -0.0604074000
_diffrn_orient_matrix_UB_33      0.0041247000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.785
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            27981
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.785
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.081
_diffrn_reflns_theta_min         2.062
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93121
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         10700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.943
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0501
_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          0.1391
_refine_ls_wR_factor_ref         0.1651
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6492
_reflns_number_total             10700
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02186_si_002.cif
_cod_data_source_block           6m
_cod_depositor_comments
'Adding full bibliography for 4033619--4033624.cif.'
_cod_database_code               4033621
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C29 H20 O2'
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.994
_reflns_odcompleteness_completeness 99.91
_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:
 C018(H018), C019(H019), C020(H020), C021(H021), C022(H022), C023(H023),
 C024(H024), C029(H029), C030(H030), C032(H032), C033(H033), C034(H034),
 C035(H035), C036(H036), C037(H037), C038(H038), C039(H039), C040(H040),
 C041(H041), C042(H042), C043(H043), C044(H044), C045(H045), C046(H046),
 C047(H047), C048(H048), C049(H049), C050(H050), C051(H051), C052(H052),
 C053(H053), C054(H054), C055(H055), C056(H056), C057(H057), C058(H058),
 C059(H059), C060(H060), C061(H061), C062(H062)
;
_shelx_res_checksum              51746
_shelx_hkl_checksum              88395
_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 1.189
_oxdiff_exptl_absorpt_empirical_full_min 0.837