Zirconium Hydrazinediido Complexes Derived from Cyclic Hydrazines and Their Role in the Catalytic Synthesis of 1,7-Annulated Indoles
Scholl, Solveig A.; Wadepohl, Hubert; Gade, Lutz H.; Organometallics 32 (2013) 937–; doi:10.1021/om301235d

data_4080052
_publ_section_title
;
 Zirconium Hydrazinediido Complexes Derived from Cyclic Hydrazines and
 Their Role in the Catalytic Synthesis of 1,7-Annulated Indoles
;
_journal_issue                   3
_journal_name_full               Organometallics
_journal_page_first              937
_journal_paper_doi               10.1021/om301235d
_journal_volume                  32
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C65 H73 N9 Zr'
_chemical_formula_weight         1071.54
_chemical_properties_physical    air-sensitive
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_ss40
_audit_creation_date
;
'Wed May 30 12:02:59 2012'
;
_audit_creation_method
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_audit_update_record             'Wed May 30 17:09:15 CEST 2012'
_cell_angle_alpha                90.00
_cell_angle_beta                 106.9281(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.08162(14)
_cell_length_b                   15.8271(2)
_cell_length_c                   17.4213(2)
_cell_measurement_reflns_used    22565
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      72.0073
_cell_measurement_theta_min      3.8484
_cell_volume                     2923.13(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2011 (Giacovazzo et al., 2011)'
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9621
_diffrn_detector_type            'Agilent EOS'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -41.00   21.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -60.0000 62

  2 omega  -22.00   22.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   57.0000   60.0000 44

  3 omega  -54.00   -3.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  125.0000  150.0000 51

  4 omega  -52.00  -12.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000   60.0000 40

  5 omega -110.00  -65.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000   60.0000 45

  6 omega  -45.00  -12.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -180.0000 33

  7 omega  -57.00  -25.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   57.0000   60.0000 32

  8 omega  -51.00  -12.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  -60.0000 39

  9 omega  -60.00   28.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   50.0000  150.0000 88

 10 omega  -46.00  -12.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  120.0000 34

 11 omega  -50.00   30.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   25.0000  -30.0000 80

 12 omega -113.00  -80.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -180.0000 33

 13 omega  -38.00  -12.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000    0.0000 26

 14 omega  -51.00  -12.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -120.0000 39

 15 omega   26.00  113.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       55.3915 -125.0000 -180.0000 87

 16 omega   25.00  124.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       55.3915   77.0000 -120.0000 99

 17 omega   25.00  125.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       55.3915   77.0000  -60.0000 100

 18 omega   26.00  111.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       55.3915   77.0000 -180.0000 85

 19 omega   26.00   89.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       55.3915   77.0000   90.0000 63

 20 omega   26.00   63.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       55.3915   77.0000  150.0000 37

 21 omega  -13.00   76.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       55.3915  -57.0000  -30.0000 89

 22 omega   25.00  113.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       55.3915   77.0000    0.0000 88

 23 omega   -1.00   85.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       55.3915  -77.0000 -120.0000 86

 24 omega   85.00  111.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   38.0000   90.0000 26

 25 omega   85.00  129.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   38.0000  -30.0000 44

 26 omega   41.00  103.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830  -50.0000  120.0000 62

 27 omega   85.00  113.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   38.0000   60.0000 28

 28 omega   81.00  107.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   77.0000   60.0000 26

 29 omega  115.00  174.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   77.0000   60.0000 59

 30 omega   86.00  121.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   38.0000   30.0000 35

 31 omega   85.00  112.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   38.0000  -60.0000 27

 32 omega   91.00  116.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   50.0000    0.0000 25

 33 omega   90.00  163.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   50.0000  -60.0000 73

 34 omega   81.00  108.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   77.0000  150.0000 27

 35 omega  129.00  156.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   77.0000    0.0000 27

 36 omega  124.00  170.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   77.0000   90.0000 46

 37 omega   89.00  170.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   50.0000 -180.0000 81

 38 omega   90.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   50.0000  -30.0000 87

 39 omega   81.00  108.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   77.0000   90.0000 27

 40 omega  123.00  162.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   77.0000  -90.0000 39

 41 omega   89.00  158.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   50.0000   30.0000 69

 42 omega   81.00  121.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   77.0000  -90.0000 40

 43 omega  119.00  146.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830  -91.0000  150.0000 27

 44 omega   81.00  107.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   77.0000  -60.0000 26

 45 omega   81.00  175.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   77.0000   30.0000 94

 46 omega   81.00  107.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   77.0000    0.0000 26

 47 omega   81.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   77.0000  120.0000 97

 48 omega   89.00  116.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   50.0000  150.0000 27

 49 omega   39.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830  -91.0000  150.0000 70

 50 omega  120.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   77.0000  150.0000 57

 51 omega   85.00  111.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   38.0000  120.0000 26

 52 omega   90.00  117.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   50.0000 -150.0000 27

 53 omega   81.00  107.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   77.0000  -30.0000 26

 54 omega   42.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830 -111.0000  120.0000 73

 55 omega   90.00  125.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   50.0000  120.0000 35

 56 omega   89.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   50.0000   90.0000 26

 57 omega   88.00  129.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   63.0000  120.0000 41

 58 omega   85.00  111.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   38.0000  -90.0000 26

 59 omega   81.00  107.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   77.0000 -150.0000 26

 60 omega   85.00  113.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   38.0000 -150.0000 28

 61 omega   85.00  112.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830 -111.0000   60.0000 27

 62 omega  123.00  152.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   38.0000   30.0000 29

 63 omega  148.00  173.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   77.0000 -180.0000 25

 64 omega   85.00  111.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   38.0000    0.0000 26

 65 omega   88.00  171.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   63.0000 -150.0000 83

 66 omega   81.00  107.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   77.0000 -180.0000 26

 67 omega   38.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830 -111.0000  -90.0000 77

 68 omega  114.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   77.0000 -120.0000 64

 69 omega   81.00  108.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   77.0000 -120.0000 27

 70 omega   90.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   50.0000 -120.0000 25

 71 omega   89.00  116.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   50.0000   60.0000 27

 72 omega   88.00  114.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   63.0000  150.0000 26

 73 omega   41.00  141.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830  -77.0000  -60.0000 100

 74 omega   90.00  117.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      110.7830   50.0000  -90.0000 27

 75 omega  -70.00   30.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000 -150.0000 100

 76 omega -115.00  -40.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -38.0000  -60.0000 75

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_orient_matrix_UB_11      -0.0142111000
_diffrn_orient_matrix_UB_12      -0.0308538000
_diffrn_orient_matrix_UB_13      -0.0860202000
_diffrn_orient_matrix_UB_21      0.1314093000
_diffrn_orient_matrix_UB_22      -0.0413012000
_diffrn_orient_matrix_UB_23      0.0287115000
_diffrn_orient_matrix_UB_31      -0.0604382000
_diffrn_orient_matrix_UB_32      -0.0825906000
_diffrn_orient_matrix_UB_33      0.0178083000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_sigmaI/netI    0.0909
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            47425
_diffrn_reflns_theta_full        66.97
_diffrn_reflns_theta_max         72.0073
_diffrn_reflns_theta_min         3.8484
_diffrn_source                   'Agilent SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.899
_exptl_absorpt_correction_T_max  0.867
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1132
_exptl_crystal_size_max          0.1653
_exptl_crystal_size_mid          0.1505
_exptl_crystal_size_min          0.0987
_platon_squeeze_details
;
;
_refine_diff_density_max         1.203
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(8)
_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     559
_refine_ls_number_reflns         11106
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0670P)^2^+0.6704P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1041
_reflns_number_gt                10597
_reflns_number_total             11106
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om301235d_si_002.cif
_cod_data_source_block           Zr-complex_3
_cod_original_cell_volume        2923.12(7)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4080052
_audit_block_refno               1507
_audit_block_usercomment         'SOSMW 006, plate, yellow'
_cell_oxdiff_length_a            11.08209(18)
_cell_oxdiff_length_b            15.8234(3)
_cell_oxdiff_length_c            17.4280(3)
_cell_oxdiff_angle_alpha         89.9795(16)
_cell_oxdiff_angle_beta          106.9645(16)
_cell_oxdiff_angle_gamma         90.0165(14)
_cell_oxdiff_volume              2923.12(9)
_cell_oxdiff_measurement_reflns_used 22565
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_theta     66.97
_reflns_odcompleteness_iscentric 1