Divergent Synthesis of Densely Substituted Arenes and Pyridines via Cyclotrimerization Reactions of Alkynyl Triazenes.
Tan, Jin-Fay; Bormann, Carl T.; Perrin, Florian G.; Chadwick, F. Mark; Severin, Kay; Cramer, Nicolai; Journal of the American Chemical Society 141 (2019) 10372–10383; doi:10.1021/jacs.9b04111

data_4128003
_publ_section_title
;
 Divergent Synthesis of Densely Substituted Arenes and Pyridines via
 Cyclotrimerization Reactions of Alkynyl Triazenes.
;
_journal_issue                   26
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10372
_journal_page_last               10383
_journal_paper_doi               10.1021/jacs.9b04111
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C32 H53 Cl2 N3 Ru2, 0.5 (C4 H10 O)'
_chemical_formula_sum            'C34 H58 Cl2 N3 O0.5 Ru2'
_chemical_formula_weight         789.87
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                85.417(5)
_cell_angle_beta                 84.226(5)
_cell_angle_gamma                66.447(5)
_cell_formula_units_Z            2
_cell_length_a                   9.0428(5)
_cell_length_b                   11.1213(6)
_cell_length_c                   18.9745(14)
_cell_measurement_reflns_used    3508
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.8580
_cell_measurement_theta_min      4.3480
_cell_volume                     1738.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     12.00 112.00   1.00    1.12    --   40.16  57.00   0.00  100
  2  \w    141.00 173.00   1.00    2.09    --  112.00  61.00   0.00   32
  3  \w    149.00 176.00   1.00    2.09    --  112.00  61.00 -30.00   27
  4  \w     87.00 146.00   1.00    2.09    --  112.00  45.00  60.00   59
  5  \w     93.00 120.00   1.00    2.09    --  112.00  61.00 -30.00   27
  6  \w     83.00 113.00   1.00    2.09    --  112.00  61.00   0.00   30
  7  \w     33.00 165.00   1.00    2.09    --  112.00 -15.00  30.00  132
  8  \w     58.00  85.00   1.00    2.09    --  112.00 -94.00 120.00   27
  9  \w     41.00 121.00   1.00    2.09    --  112.00-125.00  60.00   80
 10  \w     41.00 137.00   1.00    2.09    --  112.00 -61.00   0.00   96
 11  \w     49.00 130.00   1.00    2.09    --  112.00 -30.00-180.00   81
 12  \w     39.00 121.00   1.00    2.09    --  112.00-125.00-150.00   82
 13  \w     36.00 143.00   1.00    2.09    --  112.00 -77.00-150.00  107
 14  \w     33.00  96.00   1.00    1.12    --   40.16-125.00  60.00   63
 15  \w    -67.00  27.00   1.00    1.12    --  -40.16  57.00 -90.00   94
 16  \w    -60.00  -2.00   1.00    1.12    --  -40.16 125.00  30.00   58
 17  \w   -109.00 -18.00   1.00    1.12    --  -40.16 -57.00 120.00   91
 18  \w    -90.00 -65.00   1.00    1.12    --  -40.16-141.00 -95.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.967
_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       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7188
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.113
_diffrn_reflns_theta_min         4.341
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.655
_exptl_absorpt_correction_T_max  0.743
_exptl_absorpt_correction_T_min  0.343
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear intense brown'
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_description       plate
_exptl_crystal_F_000             818
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.131
_refine_diff_density_max         1.757
_refine_diff_density_min         -1.417
_refine_diff_density_rms         0.246
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         7188
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0799
_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^)+(0.1445P)^2^+17.5242P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2208
_refine_ls_wR_factor_ref         0.2239
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6598
_reflns_number_total             7188
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04111_si_004.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        1738.72(19)
_cod_original_formula_sum        'C34 H58 Cl2 N3 O0.50 Ru2'
_cod_database_code               4128003
_shelx_shelxl_version_number     2017/1
_shelx_res_checksum              92783
_shelx_hkl_checksum              98292