Carbonyl-Assisted Reverse Regioselective Cascade Annulation of 2-Acetylenic Ketones Triggered by Ru-Catalyzed C–H Activation
Gollapelli, Krishna Kumar; Kallepu, Shivakrishna; Govindappa, Nagendra; Nanubolu, Jagadeesh babu; Chegondi, Rambabu; Chem. Sci.  (2016) –; doi:10.1039/C6SC01456A

data_1543099
_publ_section_title
;
 Carbonyl-Assisted Reverse Regioselective Cascade Annulation of
 2-Acetylenic Ketones Triggered by Ru-Catalyzed C--H Activation
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C6SC01456A
_journal_year                    2016
_chemical_formula_moiety         'C22 H19 N O3'
_chemical_formula_sum            'C22 H19 N O3'
_chemical_formula_weight         345.38
_chemical_name_systematic
3a-hydroxy-11a-methyl-10-phenyl-3,3a,11,11a-tetrahydro-1H-cyclopenta[4,5]pyrrolo[1,2-b]isoquinoline-1,5(2H)-dione
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-01-22 deposited with the CCDC.
2016-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.7479(11)
_cell_length_b                   9.6392(6)
_cell_length_c                   19.3565(11)
_cell_measurement_reflns_used    6727
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.17
_cell_volume                     3498.0(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            38604
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.284
_diffrn_reflns_theta_min         2.104
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane and Hexane (1:4)'
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4295
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0699P)^2^+0.6748P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1297
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3486
_reflns_number_total             4295
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc01456a2.cif
_cod_data_source_block           AZ69
_cod_database_code               1543099
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.964
_shelx_estimated_absorpt_t_max   0.978
_exptl_absorpt_special_details
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_shelx_res_checksum              4102