Synthesis of (spiro)cyclopentapyridinones via Csp3-H functionalization: a post-Ugi gold-catalyzed regioselective tandem cyclization
Dipak D. Vachhani; Marzia Galli; Jeroen Jacobs; Luc Van Meervelt; Erik V. Van der Eycken; Chem.Commun. 49 (2013) 7171–; doi:10.1039/c3cc43418d

data_7109577
_publ_section_title
;
 Synthesis of (spiro)cyclopentapyridinones via Csp3-H functionalization: a
 post-Ugi gold-catalyzed regioselective tandem cyclization
;
_journal_name_full               Chem.Commun.
_journal_page_first              7171
_journal_paper_doi               10.1039/c3cc43418d
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C23 H30 N2 O3'
_chemical_formula_sum            'C23 H30 N2 O3'
_chemical_formula_weight         382.49
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-19
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                95.237(8)
_cell_angle_beta                 115.250(13)
_cell_angle_gamma                91.298(9)
_cell_formula_units_Z            2
_cell_length_a                   9.9200(14)
_cell_length_b                   10.6423(9)
_cell_length_c                   11.0407(14)
_cell_measurement_reflns_used    2919
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      28.3940
_cell_measurement_theta_min      3.6560
_cell_volume                     1047.4(2)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -47.00   45.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513   77.0000 -150.0000 92

  2 omega  -73.00    3.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -57.0000  -30.0000 76

  3 omega  -20.00   24.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -99.0000 -120.0000 44

  4 omega  -70.00   56.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513    0.0000 -180.0000 126

  5 omega    0.00   55.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701  -99.0000  120.0000 55
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0613728000
_diffrn_orient_matrix_UB_12      0.0158565000
_diffrn_orient_matrix_UB_13      -0.0581668000
_diffrn_orient_matrix_UB_21      -0.0499694000
_diffrn_orient_matrix_UB_22      -0.0258865000
_diffrn_orient_matrix_UB_23      0.0232199000
_diffrn_orient_matrix_UB_31      0.0006836000
_diffrn_orient_matrix_UB_32      0.0596738000
_diffrn_orient_matrix_UB_33      0.0343545000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7897
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.97
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58487
_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            colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0685P)^2^+0.5011P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1505
_reflns_number_gt                3503
_reflns_number_total             4280
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc43418d.txt
_cod_data_source_block           wdh1026
_cod_database_code               7109577
_chemical_oxdiff_formula         'C20 H10 H20 N2 O3'
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32