Carbene/Base-Mediated Redox Alkenylation of Isatins Using β-Substituted Organo-selenones and Aldehydes.
Bhaumik, Atanu; Azaz, Tazeen; Singh, Vikram; Khatana, Anil Kumar; Tiwari, Bhoopendra; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02188

data_4033662
_publ_section_title
;
 Carbene/Base-Mediated Redox Alkenylation of Isatins Using \b-Substituted
 Organo-selenones and Aldehydes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02188
_journal_year                    2019
_chemical_formula_moiety         'C24 H18 Br N O3'
_chemical_formula_sum            'C24 H18 Br N O3'
_chemical_formula_weight         448.30
_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_date             2016-08-08
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                65.269(11)
_cell_angle_beta                 76.006(13)
_cell_angle_gamma                75.414(12)
_cell_formula_units_Z            2
_cell_length_a                   7.5212(18)
_cell_length_b                   11.808(3)
_cell_length_c                   13.250(3)
_cell_measurement_reflns_used    2785
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.61
_cell_measurement_theta_min      2.83
_cell_volume                     1021.8(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.981
_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  0.0624
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9544
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.488
_diffrn_reflns_theta_min         1.713
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.036
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1246 before and 0.0680 after correction.
The Ratio of minimum to maximum transmission is 0.6481.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.622
_refine_diff_density_min         -0.761
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.1214
_refine_ls_R_factor_gt           0.0879
_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^)+(0.1658P)^2^+0.8097P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2631
_refine_ls_wR_factor_ref         0.2878
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2394
_reflns_number_total             3725
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02188_si_002.cif
_cod_data_source_block           sn_mh_1r_0m
_cod_database_code               4033662
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16), C17(H17),
 C18(H18), C21(H21), C22(H22), C23(H23), C24(H24)
2.b X=CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              23318
_shelx_hkl_checksum              94831
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'