Accessing the CpArNi(I) Synthon: Reactions with N-Heterocyclic Carbenes, TEMPO, Sulfur, and Selenium
Chakraborty, Uttam; Urban, Franziska; Mühldorf, Bernd; Rebreyend, Christophe; de Bruin, Bas; van Velzen, Niels; Harder, Sjoerd; Wolf, Robert; Organometallics 35 (2016) 1624–; doi:10.1021/acs.organomet.6b00084

data_4088441
_publ_section_title
;
 Accessing the CpArNi(I) Synthon: Reactions with N-Heterocyclic Carbenes,
 TEMPO, Sulfur, and Selenium
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              1624
_journal_paper_doi               10.1021/acs.organomet.6b00084
_journal_volume                  35
_journal_year                    2016
_chemical_formula_moiety         'C45 H46 Ni'
_chemical_formula_sum            'C45 H46 Ni'
_chemical_formula_weight         645.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-20
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.0972(15)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.2006(3)
_cell_length_b                   15.05392(15)
_cell_length_c                   21.1694(2)
_cell_measurement_reflns_used    18309
_cell_measurement_temperature    123(1)
_cell_measurement_theta_max      66.4330
_cell_measurement_theta_min      3.5550
_cell_volume                     6943.43(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega   11.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5337 -125.0000  -60.0000 79

  2 omega   25.00  117.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5337   77.0000   60.0000 92

  3 omega   23.00  130.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  -36.6875 107

  4 omega   20.00   65.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  150.0000 45

  5 omega   85.00  168.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000   60.0000 83

  6 omega   78.00  128.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000 -120.0000 50

  7 omega   93.00  119.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000   42.3738 26

  8 omega  142.00  168.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000 -120.0000 26

  9 omega   22.00   86.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  -60.0000 64

 10 omega   19.00   95.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000   60.0000 76

 11 omega   19.00   52.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000   90.0000 33

 12 omega   64.00  120.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000   90.0000 56

 13 omega   36.00   78.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000   42.3738 42

 14 omega   15.00  117.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5337   38.0000    0.0000 102

 15 omega    8.00  120.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5337   77.0000 -150.0000 112

 16 omega   66.00  168.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  150.0000 102

 17 omega   66.00  168.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  -30.0000 102

 18 omega   63.00  168.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000   30.0000 105

 19 omega   63.00  168.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000  -90.0000 105

 20 omega   15.00   75.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  150.0000 60

 21 omega   60.00  172.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   90.0000 112

 22 omega   63.00   73.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   64.0000 -146.4522 10
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, AtlasS2, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0026149000
_diffrn_orient_matrix_UB_12      -0.0911955000
_diffrn_orient_matrix_UB_13      0.0339358000
_diffrn_orient_matrix_UB_21      0.0060108000
_diffrn_orient_matrix_UB_22      -0.0457899000
_diffrn_orient_matrix_UB_23      -0.0625166000
_diffrn_orient_matrix_UB_31      0.0703897000
_diffrn_orient_matrix_UB_32      0.0073015000
_diffrn_orient_matrix_UB_33      0.0308329000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            34576
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.786
_diffrn_reflns_theta_min         3.569
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.018
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'reddish violet'
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       block
_exptl_crystal_F_000             2752
_exptl_crystal_size_max          0.414
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         6123
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0599P)^2^+4.3575P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1023
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5507
_reflns_number_total             6123
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om6b00084_si_003.cif
_cod_data_source_block           uc124mc
_cod_original_cell_volume        6943.42(16)
_cod_database_code               4088441
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         C45H45Ni
_reflns_odcompleteness_completeness 98.59
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C45-C44 \\sim C45A-C44
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C45 \\sim C45A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
4. Others
 Fixed Sof: H44B(0.66) H44A(0.66) H44C(0.34) H44D(0.34) C45(0.66) H45A(0.66)
 H45B(0.66) H45C(0.66) C45A(0.34) H45D(0.34) H45E(0.34) H45F(0.34) H(0.5)
 HA(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C28(H28A,H28B), C20(H20A,H20B), C36(H36A,H36B), C44(H44B,
 H44A), C44(H44C,H44D)
5.b Aromatic/amide H refined with riding coordinates:
 C39(H39), C43(H43), C31(H31), C23(H23), C32(H32), C42(H42), C40(H40), C8(H8),
 C7(H7), C24(H24), C10(H10), C11(H11), C15(H15), C27(H27), C19(H19), C35(H35),
 C18(H18), C34(H34), C16(H16), C26(H26)
5.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C37(H37A,H37B,
 H37C), C45(H45A,H45B,H45C), C45A(H45D,H45E,H45F)
;
_shelx_res_checksum              41018
_shelx_hkl_checksum              890
_olex2_submission_special_instructions 'No special instructions were received'