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_4088446
_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         'C72 H81 N2 Ni'
_chemical_formula_sum            'C72 H81 N2 Ni'
_chemical_formula_weight         1033.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.9126(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.88422(10)
_cell_length_b                   20.99784(19)
_cell_length_c                   13.29748(12)
_cell_measurement_reflns_used    21897
_cell_measurement_temperature    123(1)
_cell_measurement_theta_max      66.5360
_cell_measurement_theta_min      4.2590
_cell_volume                     2891.76(5)
_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   16.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4087   57.0000  150.0000 89

  2 omega  -21.00   52.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4087  -99.0000   60.0000 73

  3 omega  112.00  172.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   60.0000 60

  4 omega   73.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   60.0000 29

  5 omega   81.00  119.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000 -150.0000 38

  6 omega   30.00   56.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000 -150.0000 26

  7 omega   41.00   76.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -60.0000 35

  8 omega   19.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  150.0000 80

  9 omega   22.00   72.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   90.0000 50

 10 omega   33.00   59.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000 -150.0000 26

 11 omega   64.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000 -150.0000 26

 12 omega   23.00   69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000   30.0000 46

 13 omega   76.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  150.0000 26

 14 omega  105.00  146.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  150.0000 41

 15 omega   49.00  127.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -74.0000  -30.3699 78

 16 omega   16.00   42.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -74.0000  -30.3699 26

 17 omega  -99.00  -18.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4087  125.0000  150.0000 81

 18 omega   12.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4087   57.0000   30.0000 103

 19 omega   12.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4087   57.0000  -90.0000 103

 20 omega   63.00  168.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000  -90.0000 105

 21 omega   63.00  171.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000 -150.0000 108

 22 omega   63.00  168.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000  120.0000 105

 23 omega   63.00  171.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000    0.0000 108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, AtlasS2, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1239904000
_diffrn_orient_matrix_UB_12      -0.0332628000
_diffrn_orient_matrix_UB_13      0.0678166000
_diffrn_orient_matrix_UB_21      0.0553144000
_diffrn_orient_matrix_UB_22      0.0027663000
_diffrn_orient_matrix_UB_23      -0.0935212000
_diffrn_orient_matrix_UB_31      0.0607561000
_diffrn_orient_matrix_UB_32      0.0653478000
_diffrn_orient_matrix_UB_33      0.0384280000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26054
_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         66.735
_diffrn_reflns_theta_min         4.269
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85221
_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            'dark orange'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1110
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.098(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     690
_refine_ls_number_reflns         9535
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0290
_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^)+(0.0388P)^2^+0.8219P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0753
_reflns_Friedel_coverage         0.942
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                9439
_reflns_number_total             9535
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            4a.cif
_cod_data_source_block           uc137_mp
_cod_database_code               4088446
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         C85H93N2Ni
_reflns_odcompleteness_completeness 98.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.902(19) 0.098(19)
2. 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
3.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C22(H22), C25(H25)
3.b Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B), C47(H47A,H47B), C55(H55A,H55B), C63(H63A,H63B), C71(H71A,H71B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20),
 C34(H34), C35(H35), C37(H37), C38(H38), C42(H42), C43(H43), C45(H45), C46(H46),
  C50(H50), C51(H51), C53(H53), C54(H54), C58(H58), C59(H59), C61(H61),
 C62(H62), C66(H66), C67(H67), C69(H69), C70(H70)
3.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C), C40(H40A,H40B,H40C), C48(H48A,H48B,H48C), C56(H56A,H56B,H56C),
 C64(H64A,H64B,H64C), C72(H72A,H72B,H72C)
;
_shelx_res_checksum              87857
_shelx_hkl_checksum              20803
_olex2_submission_special_instructions 'No special instructions were received'