Solvent-Controlled, Tunable Domino Reaction of 3-Ylideneoxindoles with in Situ-Generated α-Aryldiazomethanes: A Facile Access to 3-Spirocyclopropyl-2-oxindole and Pyrazoloquinazolinone Scaffolds.
Ramu, Gopathi; Hari Krishna, Namballa; Pawar, Gaurav; Visweswara Sastry, K. N.; Nanubolu, Jagadeesh Babu; Nagendra Babu, Bathini; ACS omega 3 (2018) 12349–12360; doi:10.1021/acsomega.8b01857

data_4515864
_publ_section_title
;
 Solvent-Controlled, Tunable Domino Reaction of 3-Ylideneoxindoles with in
 Situ-Generated \a-Aryldiazomethanes: A Facile Access to
 3-Spirocyclopropyl-2-oxindole and Pyrazoloquinazolinone Scaffolds.
;
_journal_issue                   10
_journal_name_full               'ACS omega'
_journal_page_first              12349
_journal_page_last               12360
_journal_paper_doi               10.1021/acsomega.8b01857
_journal_volume                  3
_journal_year                    2018
_chemical_formula_moiety         'C20 H18 F N O4'
_chemical_formula_sum            'C20 H18 F N O4'
_chemical_formula_weight         355.35
_chemical_name_systematic
'ethyl 5'-fluoro-3-(4-methoxyphenyl)-2'-oxospiro[cyclopropane-1,3'-indoline]-2-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 93.02(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.081(5)
_cell_length_b                   12.345(11)
_cell_length_c                   22.898(16)
_cell_measurement_reflns_used    6367
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.122
_cell_measurement_theta_min      2.421
_cell_volume                     1717(2)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  '<i>SHELXL2014</i> (Sheldrick, 2015)'
_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0762
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            24351
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.428
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0643
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1539
_refine_ls_wR_factor_ref         0.1784
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2469
_reflns_number_total             3932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b01857_si_002.cif
_cod_data_source_block           KA313_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4515864
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.981
_shelx_res_checksum              178
_shelx_hkl_checksum              2027