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_4128002
_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         'C34 H61 Cl N6 Ru'
_chemical_formula_sum            'C34 H61 Cl N6 Ru'
_chemical_formula_weight         690.40
_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-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 115.515(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8219(4)
_cell_length_b                   32.0035(8)
_cell_length_c                   10.6169(3)
_cell_measurement_reflns_used    13408
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.1410
_cell_measurement_theta_min      4.3430
_cell_volume                     3625.1(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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1333
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_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    -10.00  22.00   1.00    1.00    --  -42.20  37.00 -90.00   32
  2  \w      1.00  59.00   1.00    1.00    --   42.20 -99.00 -30.00   58
  3  \w      1.00  32.00   1.00    1.00    --   42.20 -99.00   0.00   31
  4  \w     37.00 138.00   1.00    3.03    --  109.26 -30.00   0.00  101
  5  \w     84.00 149.00   1.00    3.03    --  109.26  45.00-120.00   65
  6  \w     84.00 173.00   1.00    3.03    --  109.26  45.00-180.00   89
  7  \w    128.00 160.00   1.00    3.03    --  109.26 111.00  30.00   32
  8  \w    110.00 149.00   1.00    3.03    --  109.26 111.00  90.00   39
  9  \w    107.00 162.00   1.00    3.03    --  109.26 111.00 120.00   55
 10  \w    102.00 172.00   1.00    3.03    --  109.26 111.00  60.00   70
 11  \w     51.00 133.00   1.00    3.03    --  109.26 -61.00  90.00   82
 12  \w     58.00  92.00   1.00    3.03    --  109.26 -94.00 -30.00   34
 13  \w     52.00 109.00   1.00    3.03    --  109.26 -94.00-120.00   57
 14  \w     77.00 103.00   1.00    3.03    --  109.26 -94.00-180.00   26
 15  \w     37.00 116.00   1.00    3.03    --  109.26-111.00  60.00   79
 16  \w     49.00 105.00   1.00    3.03    --  109.26 -94.00  90.00   56
 17  \w    -95.00  -7.00   1.00    1.00    --  -42.20 125.00   0.00   88
 18  \w   -116.00 -26.00   1.00    1.00    --  -42.20 -37.00  90.00   90
 19  \w   -108.00 -12.00   1.00    1.00    --  -42.20 -77.00-150.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_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  0.0394
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            26183
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.521
_diffrn_reflns_theta_min         4.144
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.400
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.414
_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 red'
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.259
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         7401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0286
_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^)+(0.0405P)^2^+0.6946P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0739
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6682
_reflns_number_total             7401
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04111_si_003.cif
_cod_data_source_block           shelx
_cod_database_code               4128002
_shelx_shelxl_version_number     2017/1
_shelx_res_checksum              66151
_shelx_hkl_checksum              6809