Domino reactions of diazodicarbonyl compounds with α,β-unsaturated δ-amino esters: a convenient way towards 2-oxopiperidines, dihydropyridinones and isoquinolinediones.
Medvedev, J. J.; Meleshina, M. V.; Panikorovskii, T. L.; Schneider, C.; Nikolaev, V. A.; Organic & biomolecular chemistry 13 (2015) 9107–9117; doi:10.1039/c5ob01197c

data_7154598
_publ_section_title
;
 Domino reactions of diazodicarbonyl compounds with \a,\b-unsaturated
 \d-amino esters: a convenient way towards 2-oxopiperidines,
 dihydropyridinones and isoquinolinediones.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9107
_journal_page_last               9117
_journal_paper_doi               10.1039/c5ob01197c
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C23 H23 N O4'
_chemical_formula_sum            'C23 H23 N O4'
_chemical_formula_weight         377.42
_chemical_melting_point          191
_chemical_name_systematic
'(3S*,4aR*,8aS*)-8-hydroxy-2-(4-methoxyphenyl)-8a-methyl-3-phenyl-3,4,4a,5-tetrahydroisoquinoline-1,6(2H,8aH)-dione '
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-03-31
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2015-06-10 deposited with the CCDC.
2015-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1515(8)
_cell_length_b                   9.4791(4)
_cell_length_c                   14.8569(8)
_cell_measurement_reflns_used    2030
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1860
_cell_measurement_theta_min      3.3940
_cell_volume                     1852.13(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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      293(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9968
_diffrn_measured_fraction_theta_max 0.7482
_diffrn_measurement_details
;
  1 omega  -28.00   47.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339   77.0000   30.0000 75

  2 omega  -42.00   55.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714  -19.0000 -180.0000 97
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0404982000
_diffrn_orient_matrix_UB_12      0.0470737000
_diffrn_orient_matrix_UB_13      -0.0094331000
_diffrn_orient_matrix_UB_21      0.0024630000
_diffrn_orient_matrix_UB_22      0.0186463000
_diffrn_orient_matrix_UB_23      0.0462189000
_diffrn_orient_matrix_UB_31      0.0356041000
_diffrn_orient_matrix_UB_32      -0.0549451000
_diffrn_orient_matrix_UB_33      0.0075488000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6087
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.98
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_crystal_recrystallization_method
'slow evaporation from methanol solution'
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.5(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3623
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0535P)^2^+0.2856P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1129
_reflns_number_gt                3269
_reflns_number_total             3623
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01197c2.cif
_cod_data_source_block           sem-720(2)
_cod_depositor_comments
;
          Adding full bibliography for 7154598.cif.

2018-03-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '4(C23 H23 N O4)'
_cod_original_formula_sum        'C92 H92 N4 O16'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     1509.70
_cod_database_code               7154598
_chemical_oxdiff_formula         'O4 N H23 C40'
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32