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_4128004
_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         'C22 H38 Cl N3 Ru'
_chemical_formula_sum            'C22 H38 Cl N3 Ru'
_chemical_formula_weight         481.07
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.78429(17)
_cell_length_b                   12.32688(14)
_cell_length_c                   10.75495(10)
_cell_measurement_reflns_used    33774
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.0070
_cell_measurement_theta_min      3.5360
_cell_volume                     2357.75(4)
_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    'Mercury 4.1.0 (CCDC, 2019)'
_computing_publication_material  'CIFTab (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.997
_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    -34.00  63.00   1.00    2.00    --   40.66 -38.00  90.00   97
  2  \w     26.00  92.00   1.00    2.00    --   40.66-128.00 126.00   66
  3  \w     51.00 109.00   1.00    8.00    --  112.00 -94.00  60.00   58
  4  \w     53.00 115.00   1.00    8.00    --  112.00-111.00  30.00   62
  5  \w    113.00 144.00   1.00    8.00    --  112.00 -77.00 -60.00   31
  6  \w     86.00 177.00   1.00    8.00    --  112.00  61.00-150.00   91
  7  \w    148.00 177.00   1.00    8.00    --  112.00  77.00 -90.00   29
  8  \w    146.00 178.00   1.00    8.00    --  112.00 111.00   0.00   32
  9  \w    130.00 176.00   1.00    8.00    --  112.00  77.00 -30.00   46
 10  \w    125.00 174.00   1.00    8.00    --  112.00  77.00-120.00   49
 11  \w    137.00 178.00   1.00    8.00    --  112.00 111.00-150.00   41
 12  \w    121.00 178.00   1.00    8.00    --  112.00  77.00-180.00   57
 13  \w     83.00 133.00   1.00    8.00    --  112.00  61.00-180.00   50
 14  \w     84.00 136.00   1.00    8.00    --  112.00  61.00-120.00   52
 15  \w     80.00 124.00   1.00    8.00    --  112.00  77.00 -90.00   44
 16  \w     84.00 162.00   1.00    8.00    --  112.00  61.00 -90.00   78
 17  \w    107.00 177.00   1.00    8.00    --  112.00  77.00  30.00   70
 18  \w    133.00 160.00   1.00    8.00    --  112.00  61.00 150.00   27
 19  \w    111.00 138.00   1.00    2.00    --   66.00  77.00 102.41   27
 20  \w    112.00 175.00   1.00    8.00    --  112.00  77.00 120.00   63
 21  \w    109.00 170.00   1.00    8.00    --  112.00  77.00  60.00   61
 22  \w    113.00 177.00   1.00    8.00    --  112.00  77.00 150.00   64
 23  \w     84.00 126.00   1.00    2.00    --   66.00  77.00  58.99   42
 24  \w     83.00 110.00   1.00    8.00    --  112.00  61.00 150.00   27
 25  \w     79.00 110.00   1.00    8.00    --  112.00  77.00 120.00   31
 26  \w     83.00 124.00   1.00    8.00    --  112.00  61.00  60.00   41
 27  \w     83.00 110.00   1.00    8.00    --  112.00  61.00  30.00   27
 28  \w     80.00 105.00   1.00    8.00    --  112.00  77.00  30.00   25
 29  \w     79.00 105.00   1.00    8.00    --  112.00  77.00  60.00   26
 30  \w     80.00 178.00   1.00    8.00    --  112.00  77.00  90.00   98
 31  \w     80.00 116.00   1.00    8.00    --  112.00  77.00-120.00   36
 32  \w     84.00 109.00   1.00    8.00    --  112.00  61.00 -60.00   25
 33  \w     83.00 149.00   1.00    8.00    --  112.00  61.00 -30.00   66
 34  \w     79.00 105.00   1.00    8.00    --  112.00  77.00-180.00   26
 35  \w     80.00 105.00   1.00    8.00    --  112.00  77.00-150.00   25
 36  \w     79.00 178.00   1.00    8.00    --  112.00  77.00 -60.00   99
 37  \w     79.00 171.00   1.00    8.00    --  112.00  77.00   0.00   92
 38  \w     79.00 111.00   1.00    8.00    --  112.00  77.00 150.00   32
 39  \w     51.00  86.00   1.00    8.00    --   82.00  72.00 119.75   35
 40  \w     38.00 114.00   1.00    2.00    --   70.00  76.00 178.93   76
 41  \w     41.00  67.00   1.00    2.00    --   74.00  77.00 135.77   26
 42  \w     33.00  61.00   1.00    2.00    --   66.00  77.00 102.41   28
 43  \w     34.00  62.00   1.00    2.00    --   66.00  77.00  58.99   28
 44  \w     41.00 142.00   1.00    2.00    --   74.00  77.00  -1.82  101
 45  \w     79.00 126.00   1.00    8.00    --  112.00  77.00 -30.00   47
 46  \w     38.00  66.00   1.00    2.00    --   70.00  76.00 -18.44   28
 47  \w     35.00  61.00   1.00    2.00    --   66.00  75.00 -32.89   26
 48  \w     30.00  55.00   1.00    2.00    --   62.00  77.00 -59.23   25
 49  \w     33.00  72.00   1.00    2.00    --   66.00  77.00 -95.60   39
 50  \w     34.00 130.00   1.00    2.00    --   66.00  76.00-155.04   96
 51  \w     16.00  41.00   1.00    2.00    --   50.00  81.00-124.59   25
 52  \w     21.00  46.00   1.00    2.00    --   54.00  79.00-174.36   25
 53  \w     20.00  45.00   1.00    2.00    --   54.00  81.00-116.31   25
 54  \w     16.00  41.00   1.00    2.00    --   50.00  82.00 -37.70   25
 55  \w     21.00  46.00   1.00    2.00    --   54.00  79.00  12.90   25
 56  \w     20.00  45.00   1.00    2.00    --   54.00  81.00  56.49   25
 57  \w     20.00  45.00   1.00    2.00    --   54.00  81.00 105.58   25
 58  \w     21.00  46.00   1.00    2.00    --   54.00  79.00 140.03   25
 59  \w      0.00  25.00   1.00    2.00    --   38.00  93.00 -52.46   25
 60  \w      0.00  25.00   1.00    2.00    --   38.00  91.00-140.97   25
 61  \w      1.00  69.00   1.00    2.00    --   40.66 -99.00   0.00   68
 62  \w     33.00  94.00   1.00    2.00    --   40.66-142.00 -43.00   61
 63  \w     51.00 107.00   1.00    8.00    --  112.00 -94.00-150.00   56
 64  \w     43.00 116.00   1.00    8.00    --  112.00-111.00 -60.00   73
 65  \w     37.00  92.00   1.00    8.00    --  112.00 -77.00 -60.00   55
 66  \w     41.00 116.00   1.00    8.00    --  112.00-111.00-180.00   75
 67  \w     41.00 100.00   1.00    8.00    --  112.00-111.00 150.00   59
 68  \w    -40.00 -13.00   1.00    2.00    --  -40.66 -57.00-120.00   27
 69  \w    -82.00 -16.00   1.00    2.00    --  -40.66 -38.00   0.00   66
 70  \w   -113.00 -14.00   1.00    2.00    --  -40.66 -57.00 120.00   99
 71  \w   -112.00 -41.00   1.00    2.00    --  -40.66 -57.00-120.00   71
;
_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  0.0344
_diffrn_reflns_av_unetI/netI     0.0106
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            43379
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.073
_diffrn_reflns_theta_min         4.805
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.491
_exptl_absorpt_correction_T_max  0.705
_exptl_absorpt_correction_T_min  0.234
_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 purple'
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       prism
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.172
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.00012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2583
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0339P)^2^+3.5753P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0768
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2528
_reflns_number_total             2583
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04111_si_002.cif
_cod_data_source_block           fmc222
_cod_database_code               4128004
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.201
_shelx_estimated_absorpt_t_max   0.401
_shelx_res_checksum              34480
_shelx_hkl_checksum              73734