A novel one pot four-component reaction for the efficient synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-3′-carboxylate and trifluoromethylated spiro[indole-3,4′-pyrano[2,3-c]pyrazole] derivatives using recyclable PEG-400
Karnakar, K.; Ramesh, K.; Reddy, K. Harsha Vardhan; Anil Kumar, B. S. P.; Nanubonula, Jagadeesh Babu; Nageswar, Y. V. D.; New J. Chem. 39 (2015) 8978–; doi:10.1039/C5NJ01448D

data_7055089
_publ_section_title
;
 A novel one pot four-component reaction for the efficient synthesis of
 spiro[indoline-3,4&#x2032;-pyrano[2,3-c]pyrazole]-3&#x2032;-carboxylate
 and trifluoromethylated spiro[indole-3,4&#x2032;-pyrano[2,3-c]pyrazole]
 derivatives using recyclable PEG-400
;
_journal_issue                   11
_journal_name_full               'New J. Chem.'
_journal_page_first              8978
_journal_paper_doi               10.1039/C5NJ01448D
_journal_volume                  39
_journal_year                    2015
_chemical_formula_moiety         'C22 H14 Br N5 O4, C3 H6 O'
_chemical_formula_sum            'C25 H20 Br N5 O5'
_chemical_formula_weight         550.37
_chemical_name_systematic
'Methyl 6'-amino-5-bromo-5'-cyano-2-oxo-1'-phenyl-1'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-3'-carboxylate'
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-07-09 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                71.325(4)
_cell_angle_beta                 71.161(4)
_cell_angle_gamma                78.620(4)
_cell_formula_units_Z            2
_cell_length_a                   10.107(3)
_cell_length_b                   11.058(3)
_cell_length_c                   12.667(3)
_cell_measurement_reflns_used    5040
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.86
_cell_measurement_theta_min      2.41
_cell_volume                     1262.3(6)
_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 0.998
_diffrn_measured_fraction_theta_max 0.949
_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  0.0217
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14880
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         1.768
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.673
_exptl_absorpt_correction_T_max  0.643
_exptl_absorpt_correction_T_min  0.540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.290
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         5935
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0764P)^2^+0.2645P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1409
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4013
_reflns_number_total             5935
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5nj01448d2.cif
_cod_data_source_block           AU92M
_cod_depositor_comments          'Adding full bibliography for 7055089.cif.'
_cod_original_cell_volume        1262.4(6)
_cod_database_code               7055089
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.540
_shelx_estimated_absorpt_t_max   0.643
_exptl_absorpt_special_details
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_shelx_res_checksum              99376