Reaction of Phenyl Iso(thio)cyanate with N-Heterocyclic Carbene-Supported Nickel Complexes: Formation of Nickelacycles
Pelties, Stefan; Wolf, Robert; Organometallics 35 (2016) 2722–; doi:10.1021/acs.organomet.6b00473

data_4088819
_publ_section_title
;
 Reaction of Phenyl Iso(thio)cyanate with N-Heterocyclic Carbene-Supported
 Nickel Complexes: Formation of Nickelacycles
;
_journal_issue                   16
_journal_name_full               Organometallics
_journal_page_first              2722
_journal_paper_doi               10.1021/acs.organomet.6b00473
_journal_volume                  35
_journal_year                    2016
_chemical_formula_moiety         'C42 H49 N3 Ni O'
_chemical_formula_sum            'C42 H49 N3 Ni O'
_chemical_formula_weight         670.55
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-10
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                84.582(2)
_cell_angle_beta                 82.009(2)
_cell_angle_gamma                89.3620(18)
_cell_formula_units_Z            4
_cell_length_a                   10.3147(2)
_cell_length_b                   18.7357(5)
_cell_length_c                   19.4834(6)
_cell_measurement_reflns_used    20928
_cell_measurement_temperature    123(1)
_cell_measurement_theta_max      66.5120
_cell_measurement_theta_min      4.3080
_cell_volume                     3712.00(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2548
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
  1 omega  -31.00   67.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.5337  -57.0000  -30.0000 98

  2 omega   -3.00   76.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.5337 -125.0000  -90.0000 79

  3 omega   12.00  107.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.5337   57.0000  120.0000 95

  4 omega   54.00  127.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000 -145.1895 73

  5 omega   19.00  122.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -59.0000  132.7374 103

  6 omega   40.00  121.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000 -180.0000 81

  7 omega   81.00  116.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000  -31.8179 35

  8 omega   29.00   88.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  -30.0000 59

  9 omega   20.00   77.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -30.0000 57

 10 omega   17.00   43.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000   30.0000 26

 11 omega   54.00   80.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000   30.0000 26

 12 omega   29.00   74.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  150.0000 45

 13 omega   15.00   43.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000 -180.0000 28

 14 omega   47.00  151.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000 -180.0000 104

 15 omega   32.00   77.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000  150.0000 45

 16 omega  128.00  174.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000 -180.0000 46

 17 omega   31.00   67.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000  -31.8179 36

 18 omega   93.00  121.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  -30.0000 28

 19 omega   19.00   75.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000 -150.0000 56

 20 omega   80.00  106.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000 -150.0000 26

 21 omega  111.00  170.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000 -150.0000 59

 22 omega   74.00   99.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000   60.0000 25

 23 omega  127.00  165.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000   60.0000 38

 24 omega   24.00   60.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  120.0000 36

 25 omega   24.00   77.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000    0.0000 53

 26 omega   31.00   78.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000  105.3170 47

 27 omega  106.00  132.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000  105.3170 26

 28 omega   56.00   82.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000  -90.0000 26

 29 omega   75.00  132.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000   76.1577 57

 30 omega   17.00   43.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000   76.1577 26

 31 omega  -68.00   34.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.5337   38.0000 -180.0000 102

 32 omega    8.00  120.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.5337   77.0000 -150.0000 112

 33 omega    8.00  120.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.5337   77.0000  -60.0000 112

 34 omega   12.00  115.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.5337   57.0000   60.0000 103

 35 omega   63.00  168.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000   60.0000 105

 36 omega   60.00  119.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -120.0000 59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, AtlasS2, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0133673000
_diffrn_orient_matrix_UB_12      0.0328112000
_diffrn_orient_matrix_UB_13      0.0682676000
_diffrn_orient_matrix_UB_21      0.1502114000
_diffrn_orient_matrix_UB_22      -0.0016424000
_diffrn_orient_matrix_UB_23      -0.0177940000
_diffrn_orient_matrix_UB_31      -0.0022003000
_diffrn_orient_matrix_UB_32      0.0757807000
_diffrn_orient_matrix_UB_33      -0.0381420000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            47713
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.721
_diffrn_reflns_theta_min         3.454
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.012
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.775
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       needle
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          0.4458
_exptl_crystal_size_mid          0.1609
_exptl_crystal_size_min          0.0796
_refine_diff_density_max         0.805
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     891
_refine_ls_number_reflns         12990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0581
_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^)+(0.0569P)^2^+12.0363P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1725
_refine_ls_wR_factor_ref         0.1773
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11233
_reflns_number_total             12990
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om6b00473_si_006.cif
_cod_data_source_block           ap
_cod_original_cell_volume        3711.99(16)
_cod_database_code               4088819
_chemical_oxdiff_formula         'C168 H196 N12 Ni4 O4'
_reflns_odcompleteness_completeness 98.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C30) = Uanis(C30A) = Uanis(C29A) = Uanis(C29)
Uanis(C71) = Uanis(C71A) = Uanis(C72A) = Uanis(C72)
3. Others
 Fixed Sof: H70(0.65) H70A(0.35) H28(0.6) H28A(0.4) C71(0.65) H71A(0.65)
 H71B(0.65) H71C(0.65) C72(0.65) H72A(0.65) H72B(0.65) H72C(0.65) C29(0.6)
 H29A(0.6) H29B(0.6) H29C(0.6) C30(0.6) H30A(0.6) H30B(0.6) H30C(0.6) C30A(0.4)
 H30D(0.4) H30E(0.4) H30F(0.4) C29A(0.4) H29D(0.4) H29E(0.4) H29F(0.4)
 C71A(0.35) H71D(0.35) H71E(0.35) H71F(0.35) C72A(0.35) H72D(0.35) H72E(0.35)
 H72F(0.35)
4.a Ternary CH refined with riding coordinates:
 C25(H25), C40(H40), C82(H82), C67(H67), C70(H70), C70(H70A), C79(H79),
 C28(H28), C28(H28A), C37(H37)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C64(H64), C48(H48), C35(H35), C58(H58), C63(H63), C56(H56), C65(H65),
 C60(H60), C77(H77), C8(H8), C57(H57), C5(H5), C47(H47), C21(H21), C76(H76),
 C14(H14), C23(H23), C59(H59), C18(H18), C9(H9), C10(H10), C75(H75), C50(H50),
 C17(H17), C54(H54), C33(H33), C16(H16), C22(H22), C52(H52), C12(H12), C15(H15),
  C51(H51), C34(H34), C11(H11), C53(H53)
4.c Idealised Me refined as rotating group:
 C83(H83A,H83B,H83C), C84(H84A,H84B,H84C), C68(H68A,H68B,H68C), C27(H27A,H27B,
 H27C), C69(H69A,H69B,H69C), C41(H41A,H41B,H41C), C80(H80A,H80B,H80C), C42(H42A,
 H42B,H42C), C26(H26A,H26B,H26C), C38(H38A,H38B,H38C), C71(H71A,H71B,H71C),
 C39(H39A,H39B,H39C), C81(H81A,H81B,H81C), C72(H72A,H72B,H72C), C29(H29A,H29B,
 H29C), C30(H30A,H30B,H30C), C30A(H30D,H30E,H30F), C29A(H29D,H29E,H29F),
 C71A(H71D,H71E,H71F), C72A(H72D,H72E,H72F)
;
_shelx_res_checksum              96268
_shelx_hkl_checksum              32403
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'