Ruthenium(II)-Catalyzed Redox-Free [3 + 2] Cycloaddition of N-Sulfonyl Aromatic Aldimines with Maleimides.
Tamizmani, Masilamani; Ramesh, Balu; Jeganmohan, Masilamani; The Journal of organic chemistry 83 (2018) 3746–3755; doi:10.1021/acs.joc.8b00102

data_4035492
_publ_section_title
;
 Ruthenium(II)-Catalyzed Redox-Free [3 + 2] Cycloaddition of N-Sulfonyl
 Aromatic Aldimines with Maleimides.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3746
_journal_page_last               3755
_journal_paper_doi               10.1021/acs.joc.8b00102
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C27 H31 N2 O3 Ru S, F6 Sb'
_chemical_formula_sum            'C27 H31 F6 N2 O3 Ru S Sb'
_chemical_formula_weight         800.42
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-12-01
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.544(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9916(6)
_cell_length_b                   21.3314(11)
_cell_length_c                   13.3154(6)
_cell_measurement_reflns_used    9178
_cell_measurement_temperature    296
_cell_measurement_theta_max      22.50
_cell_measurement_theta_min      2.43
_cell_volume                     3078.8(3)
_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)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            43649
_diffrn_reflns_theta_full        26.91
_diffrn_reflns_theta_max         26.91
_diffrn_reflns_theta_min         2.11
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.503
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1206 before and 0.0474 after correction.
The Ratio of minimum to maximum transmission is 0.9017.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.875
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         6571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1412
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1072P)^2^+4.8103P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1796
_refine_ls_wR_factor_ref         0.2304
_reflns_number_gt                3335
_reflns_number_total             6571
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b00102_si_003.cif
_cod_data_source_block           ru1
_cod_database_code               4035492
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00W(H00W)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00L(H00L), C00M(H00M), C00N(H00N), C00Q(H00Q), C00R(H00R), C00T(H00T)
2.c Idealised Me refined as rotating group:
 C00U(H00A,H00B,H00D), C00X(H00E,H00K,H00O), C010(H01A,H01B,H01C), C011(H01D,
 H01E,H01F), C012(H01G,H01H,H01I), C013(H01J,H01K,H01L)
;
_olex2_submission_special_instructions 'No special instructions were received'