Rh-Catalyzed Chemo-, Stereo- and Regioselective C-H Cascade Annulation of indolyloxopropanenitriles for Pyranoindoles
Kotipalli, Ramesh; Undamatla, Suribabu; Nanubolu, Jagadesh Babu; Maddi, Sridhar Reddy; Chemical Communications  (2023) –; doi:10.1039/D3CC02762G

data_7131901
_publ_section_title
;
 Rh-Catalyzed Chemo-, Stereo- and Regioselective C-H Cascade Annulation of
 indolyloxopropanenitriles for Pyranoindoles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC02762G
_journal_year                    2023
_chemical_formula_moiety         'C22 H14 N2 O3'
_chemical_formula_sum            'C22 H14 N2 O3'
_chemical_formula_weight         354.35
_chemical_name_systematic
(Z)-2-(1-methyl-3-oxo-1-phenyl-3,10-dihydrofuro[3',4':5,6]pyrano[4,3-b]indol-5(1H)-ylidene)acetonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-01-07 deposited with the CCDC.	2023-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.143(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8625(12)
_cell_length_b                   24.973(3)
_cell_length_c                   7.5384(10)
_cell_measurement_reflns_used    6240
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.916
_cell_measurement_theta_min      2.359
_cell_volume                     1731.7(4)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            22582
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         3.055
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             736
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone'
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 896 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3617
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0436P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_full    0.875
_reflns_Friedel_fraction_max     0.825
_reflns_number_gt                2359
_reflns_number_total             3617
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02762g2.cif
_cod_data_source_block           KB658_0m_a
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7131901
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.976
_shelx_res_checksum              13043
_shelx_hkl_checksum              10581