Synthesis of Diketohexenoic Acid Derivatives by Alkenylation of Indoles and Pyrroles with 4-Pyrones.
Obydennov, Dmitrii L.; Pan'kina, Ekaterina O.; Sosnovskikh, Vyacheslav Y.; The Journal of organic chemistry 81 (2016) 12532–12539; doi:10.1021/acs.joc.6b02364

data_4037450
_publ_section_title
;
 Synthesis of Diketohexenoic Acid Derivatives by Alkenylation of Indoles
 and Pyrroles with 4-Pyrones.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12532
_journal_page_last               12539
_journal_paper_doi               10.1021/acs.joc.6b02364
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C16 H19 N O6'
_chemical_formula_sum            'C16 H19 N O6'
_chemical_formula_weight         321.32
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-10-10
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                75.458(5)
_cell_angle_beta                 70.092(6)
_cell_angle_gamma                70.295(7)
_cell_formula_units_Z            2
_cell_length_a                   9.1149(6)
_cell_length_b                   9.5692(7)
_cell_length_c                   10.4084(6)
_cell_measurement_reflns_used    2996
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      30.1960
_cell_measurement_theta_min      2.5300
_cell_volume                     794.03(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.8677
_diffrn_measurement_details
;
  1 omega  -25.00   12.00   1.0000    6.0700
omega____ theta____ kappa____ phi______ frames
    -      -20.7924  -99.0000   90.0000 37

  2 omega  -21.00   19.00   1.0000    6.0700
omega____ theta____ kappa____ phi______ frames
    -      -20.7924  -99.0000 -120.0000 40

  3 omega  -97.00  -36.00   1.0000    6.0700
omega____ theta____ kappa____ phi______ frames
    -      -20.7924 -178.0000  -60.0000 61

  4 omega    3.00   87.00   1.0000    6.0700
omega____ theta____ kappa____ phi______ frames
    -       23.2924   57.0000    0.0000 84

  5 omega   -2.00   91.00   1.0000    6.0700
omega____ theta____ kappa____ phi______ frames
    -       23.2924   38.0000  -90.0000 93

  6 omega  -45.00   49.00   1.0000    6.0700
omega____ theta____ kappa____ phi______ frames
    -       23.2924  -38.0000   90.0000 94
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0851096000
_diffrn_orient_matrix_UB_12      0.0326434000
_diffrn_orient_matrix_UB_13      0.0139740000
_diffrn_orient_matrix_UB_21      0.0072191000
_diffrn_orient_matrix_UB_22      0.0604724000
_diffrn_orient_matrix_UB_23      0.0230746000
_diffrn_orient_matrix_UB_31      0.0110082000
_diffrn_orient_matrix_UB_32      0.0403363000
_diffrn_orient_matrix_UB_33      -0.0682122000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7491
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         30.77
_diffrn_reflns_theta_min         2.29
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4301
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0880P)^2^+0.0880P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1445
_reflns_number_gt                3470
_reflns_number_total             4301
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02364_si_002.cif
_cod_data_source_block           exp_238
_cod_original_cell_volume        794.03(9)
_cod_database_code               4037450
_chemical_oxdiff_formula         C20H10NO
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22