Ruthenium(II)-Catalyzed C-H (Hetero)Arylation of Alkenylic 1,n-Diazines (n = 2, 3, and 4): Scope, Mechanism, and Application in Tandem Hydrogenations.
Gramage-Doria, Rafael; Achelle, Sylvain; Bruneau, Christian; Robin-le Guen, Françoise; Dorcet, Vincent; Roisnel, Thierry; The Journal of organic chemistry 83 (2018) 1462–1477; doi:10.1021/acs.joc.7b03024

data_4033425
_publ_section_title
;
 Ruthenium(II)-Catalyzed C-H (Hetero)Arylation of Alkenylic 1,n-Diazines
 (n = 2, 3, and 4): Scope, Mechanism, and Application in Tandem
 Hydrogenations.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1462
_journal_page_last               1477
_journal_paper_doi               10.1021/acs.joc.7b03024
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H18 N2 S2'
_chemical_formula_sum            'C20 H18 N2 S2'
_chemical_formula_weight         350.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 98.667(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   42.452(3)
_cell_length_b                   8.5066(5)
_cell_length_c                   9.6005(7)
_cell_measurement_reflns_used    6862
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.80
_cell_measurement_wavelength     0.71073
_cell_volume                     3427.4(4)
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2014)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_h_min       -54
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.555
_diffrn_reflns_theta_min         2.443
_exptl_absorpt_coefficient_mu    0.314
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.14(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         3939
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+5.0675P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1167
_reflns_number_gt                3598
_reflns_number_total             3939
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b03024_si_002.cif
_cod_data_source_block           RG_A242
_cod_depositor_comments
;
The following automatic conversions were performed:

'_space_group_crystal_system' value 'Monoclinic' changed to
'monoclinic' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4033418--4033425.cif.

2020-04-04
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C20 H18 N2 S2)'
_cod_original_formula_sum        'C40 H36 N4 S4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     700.97
_cod_database_code               4033425
_shelx_res_checksum              30448
_shelx_hkl_checksum              45484