Enantioselective Synthesis of Dihydrospiro[indoline-3,4'-pyrano[2,3-c]pyrazole] Derivatives via Michael/Hemiketalization Reaction.
Kumarswamyreddy, Nandarapu; Kesavan, Venkitasamy; Organic letters 18 (2016) 1354–1357; doi:10.1021/acs.orglett.6b00287

data_1555495
_publ_section_title
;
 Enantioselective Synthesis of
 Dihydrospiro[indoline-3,4'-pyrano[2,3-c]pyrazole] Derivatives via
 Michael/Hemiketalization Reaction.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1354
_journal_page_last               1357
_journal_paper_doi               10.1021/acs.orglett.6b00287
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H22 Br N3 O5, 0.5H2O'
_chemical_formula_sum            'C24 H22 Br N3 O5.5'
_chemical_formula_weight         520.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8376(5)
_cell_length_b                   12.9227(6)
_cell_length_c                   14.0967(5)
_cell_measurement_reflns_used    7700
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.41
_cell_measurement_theta_min      2.23
_cell_volume                     2338.59(16)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34056
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.129
_diffrn_reflns_theta_min         2.138
_exptl_absorpt_coefficient_mu    1.801
_exptl_absorpt_correction_T_max  0.6699
_exptl_absorpt_correction_T_min  0.6141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1033 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4645
_refine_ls_number_restraints     124
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0590P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1161
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2930
_reflns_number_total             4645
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00287_si_002.cif
_cod_data_source_block           NEW
_cod_original_formula_sum        'C24 H22 Br N3 O5.50'
_cod_database_code               1555495
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.614
_shelx_estimated_absorpt_t_max   0.662
_shelx_res_checksum              4361
_shelx_hkl_checksum              84004