Fridel-Crafts Alkylation of Arenes with Indolyl Alcohols for Construction of 3,3-Disubstituted Oxindoles
wang, xiaoxiao; Liu, Jian; Xu, Lubin; Hao, Zhihui; Wang, Liang; Xiao, Jian; RSC Adv.  (2015) –; doi:10.1039/C5RA21919A

data_7223325
_publ_section_title
;
 Fridel-Crafts Alkylation of Arenes with Indolyl Alcohols for Construction
 of 3,3-Disubstituted Oxindoles
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA21919A
_journal_year                    2015
_chemical_formula_sum            'C27 H19 N2 O2'
_chemical_formula_weight         403.44
_chemical_name_systematic
1-benzyl-3-(furan-2-yl)-3-(1H-indol-3-yl)indolin-2-one
_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   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-10-20 deposited with the CCDC.
2015-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                87.145(4)
_cell_angle_beta                 75.225(4)
_cell_angle_gamma                84.729(4)
_cell_formula_units_Z            2
_cell_length_a                   9.1713(12)
_cell_length_b                   10.4692(14)
_cell_length_c                   11.6564(16)
_cell_measurement_reflns_used    9989
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      3.06
_cell_volume                     1077.2(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22099
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.530
_diffrn_reflns_theta_min         3.061
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       prism
_exptl_crystal_F_000             422
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate/petroleum ether'
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.359
_exptl_crystal_size_min          0.297
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0561
_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^)+(0.0794P)^2^+0.3235P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1473
_refine_ls_wR_factor_ref         0.1646
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3646
_reflns_number_total             4941
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra21919a2.cif
_cod_data_source_block           1RAW
_cod_database_code               7223325
_shelx_estimated_absorpt_t_min   0.962
_shelx_estimated_absorpt_t_max   0.977
_shelxl_version_number           2013-4
_shelx_res_checksum              7252