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_4088442
_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 H45 Ni Se, C3 H3'
_chemical_formula_sum            'C48 H48 Ni Se'
_chemical_formula_weight         762.53
_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   geom
_audit_creation_date             2015-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                93.5632(19)
_cell_angle_beta                 113.434(2)
_cell_angle_gamma                115.153(2)
_cell_formula_units_Z            2
_cell_length_a                   12.2418(2)
_cell_length_b                   13.8410(3)
_cell_length_c                   14.1751(3)
_cell_measurement_reflns_used    36261
_cell_measurement_temperature    123(1)
_cell_measurement_theta_max      74.1930
_cell_measurement_theta_min      3.5190
_cell_volume                     1915.90(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
;
_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 4.1818
_diffrn_detector_type            TitanS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega  -74.00   20.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -44.0756   77.0000  120.0000 94

  2 omega   20.00  113.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0756   57.0000    0.0000 93

  3 omega  -23.00   67.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0756  -57.0000 -150.0000 90

  4 omega   43.00  121.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000 -180.0000 78

  5 omega   23.00   55.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000 -120.0000 32

  6 omega   95.00  139.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   30.0000  -90.0000 44

  7 omega  100.00  127.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  125.0000  150.0000 27

  8 omega   34.00  119.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000    0.0000 85

  9 omega  136.00  162.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  125.0000  150.0000 26

 10 omega   71.00   99.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000    0.0000 28

 11 omega   89.00  115.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000  150.0000 26

 12 omega   73.00  108.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000 -120.0000 35

 13 omega   37.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000   90.0000 54

 14 omega   33.00  109.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000 -180.0000 76

 15 omega   38.00   68.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000   60.0000 30

 16 omega   28.00  105.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000   60.0000 77

 17 omega   90.00  120.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000   60.0000 30

 18 omega   57.00  129.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -61.0000 -180.0000 72

 19 omega  143.00  170.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   30.0000  -90.0000 27

 20 omega   32.00   87.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000   30.0000 55

 21 omega   23.00   89.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000    0.0000 66

 22 omega   92.00  166.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   30.0000  -60.0000 74

 23 omega  100.00  134.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -79.0000    1.8774 34

 24 omega  120.00  171.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000  150.0000 51

 25 omega   83.00  166.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   53.0000 -146.8928 83

 26 omega   38.00   64.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -79.0000    1.8774 26

 27 omega  -49.00   27.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -44.0756   37.0000   30.0000 76

 28 omega   20.00  113.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0756   57.0000  120.0000 93

 29 omega   14.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0756   77.0000   30.0000 102

 30 omega   20.00  113.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0756   57.0000 -120.0000 93

 31 omega   74.00  176.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000   60.0000 102

 32 omega   82.00  173.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000  120.0000 91

 33 omega   77.00  174.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   69.0000  -25.8546 97

 34 omega   79.00  174.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000  -60.0000 95

 35 omega   82.00  173.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000   60.0000 91

 36 omega   74.00  176.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000 -120.0000 102

 37 omega   74.00  176.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000    0.0000 102

 38 omega   74.00  176.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000 -150.0000 102

 39 omega   33.00  135.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -77.0000 -180.0000 102

 40 omega   79.00  174.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000  150.0000 95

 41 omega   74.00  176.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000  -90.0000 102

 42 omega   23.00  109.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000    0.0000 86

 43 omega   74.00  176.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000  -60.0000 102

 44 omega   74.00  176.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000   30.0000 102

 45 omega   79.00  174.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000  120.0000 95

 46 omega   79.00  174.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000 -180.0000 95

 47 omega  -49.00   27.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -44.0756   37.0000  -60.0000 76

 48 omega   14.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0756   77.0000  -30.0000 102

 49 omega   14.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0756   77.0000  -90.0000 102

 50 omega   14.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0756   77.0000  150.0000 102

 51 omega   76.00  174.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   71.0000   -8.5648 98

 52 omega   79.00  174.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000   90.0000 95

 53 omega   74.00  176.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000 -180.0000 102

 54 omega   74.00  176.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000   15.2964 102

 55 omega   79.00  174.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000  -30.0000 95

 56 omega   74.00   99.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000  120.0000 25

 57 omega   74.00  176.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000  150.0000 102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'GV1000, TitanS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0144775000
_diffrn_orient_matrix_UB_12      0.0982539000
_diffrn_orient_matrix_UB_13      0.0388369000
_diffrn_orient_matrix_UB_21      0.1547645000
_diffrn_orient_matrix_UB_22      0.0650392000
_diffrn_orient_matrix_UB_23      0.0768548000
_diffrn_orient_matrix_UB_31      0.0251075000
_diffrn_orient_matrix_UB_32      0.0500616000
_diffrn_orient_matrix_UB_33      -0.0882837000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            58042
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.454
_diffrn_reflns_theta_min         3.538
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'GV1000 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.047
_exptl_absorpt_correction_T_max  0.823
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35e (release 07-10-2014 CrysAlis171 .NET)
(compiled Oct  7 2014,17:20:27)
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            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.2441
_exptl_crystal_size_mid          0.1605
_exptl_crystal_size_min          0.1368
_refine_diff_density_max         1.680
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         7771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0620P)^2^+2.4200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1256
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7446
_reflns_number_total             7771
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            6.cif
_cod_data_source_block           fu40
_cod_original_cell_volume        1915.91(8)
_cod_database_code               4088442
_chemical_oxdiff_formula         'C48 H48 Ni1 Se1'
_reflns_odcompleteness_completeness 100.00
_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. Others
 Fixed Sof: Se1(0.7) Se1A(0.3)
3.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C12(H12A,H12B), C36(H36A,H36B), C28(H28A,H28B), C44(H44A,H44B)
3.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C7(H7), C8(H8), C15(H15), C35(H35), C31(H31), C19(H19), C34(H34),
 C18(H18), C11(H11), C23(H23), C27(H27), C32(H32), C10(H10), C43(H43), C26(H26),
  C24(H24), C39(H39), C42(H42), C40(H40), C46(H46), C47(H47), C48(H48)
3.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C37(H37A,H37B,H37C), C29(H29A,H29B,H29C), C13(H13A,H13B,
 H13C), C45(H45A,H45B,H45C)
;
_shelx_res_checksum              41728
_shelx_hkl_checksum              54036
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'