Indium/Fe(III) - mediated regioselective β-cross-coupling aldol type addition reaction of activated alkenes with isatins/isatinimines in aqueous media
Meshram, Harshadas Mitaram; A., Sanjeeva Kumar; Ramesh, Palakuri; G., Santosh Kumar; Nanubolu, Jagadeesh Babu; Prabhakar Rao, Tadikamalla; RSC Adv.  (2015) –; doi:10.1039/C5RA07216F

data_7220693
_publ_section_title
;
 Indium/Fe(III) - mediated regioselective \b-cross-coupling aldol type
 addition reaction of activated alkenes with isatins/isatinimines in
 aqueous media
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA07216F
_journal_year                    2015
_chemical_formula_moiety         'C13 H14 Br N O3'
_chemical_formula_sum            'C13 H14 Br N O3'
_chemical_formula_weight         312.16
_chemical_name_common            '5-bromo-3-hydroxy 3-(3-oxopentylindolin-2-one'
_chemical_name_systematic
; 
 5-bromo-3-hydroxy 3-(3-oxopentyl)indolin-2-one  
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-07-16 deposited with the CCDC.
2015-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                71.939(3)
_cell_angle_beta                 78.573(4)
_cell_angle_gamma                82.292(4)
_cell_formula_units_Z            4
_cell_length_a                   7.5781(13)
_cell_length_b                   13.148(2)
_cell_length_c                   14.903(3)
_cell_measurement_reflns_used    3385
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.01
_cell_measurement_theta_min      2.49
_cell_volume                     1379.5(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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13331
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    2.979
_exptl_absorpt_correction_T_max  0.8415
_exptl_absorpt_correction_T_min  0.6471
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0558P)^2^+0.8413P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1225
_reflns_number_gt                3481
_reflns_number_total             4833
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra07216f2.cif
_cod_data_source_block           ao69m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_database_code               7220693