Ru(II)-Catalyzed C-H Functionalization on Maleimides with Electrophiles: A Demonstration of Umpolung Strategy.
Dana, Suman; Mandal, Anup; Sahoo, Harekrishna; Baidya, Mahiuddin; Organic letters 19 (2017) 1902–1905; doi:10.1021/acs.orglett.7b00674

data_1545956
_publ_section_title
;
 Ru(II)-Catalyzed C-H Functionalization on Maleimides with Electrophiles:
 A Demonstration of Umpolung Strategy.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1902
_journal_page_last               1905
_journal_paper_doi               10.1021/acs.orglett.7b00674
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C17 H13 N O3 Se'
_chemical_formula_weight         358.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.605(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.8061(9)
_cell_length_b                   5.9523(2)
_cell_length_c                   13.3383(6)
_cell_measurement_reflns_used    3731
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.11
_cell_measurement_theta_min      2.66
_cell_volume                     1493.00(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0304
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
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_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9710
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.166
_exptl_absorpt_coefficient_mu    2.527
_exptl_absorpt_correction_T_max  0.786
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0160(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0218P)^2^+1.0507P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0725
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1960
_reflns_number_total             2620
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00674_si_002.cif
_cod_data_source_block           imide
_cod_database_code               1545956
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.571
_shelx_estimated_absorpt_t_max   0.786
_shelx_res_checksum              21071
_shelx_hkl_checksum              17993