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_4088445
_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         'C56 H65 N2 Ni'
_chemical_formula_sum            'C56 H65 N2 Ni'
_chemical_formula_weight         824.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-09-15
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.0662(11)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.7545(3)
_cell_length_b                   11.82467(14)
_cell_length_c                   27.9694(3)
_cell_measurement_reflns_used    30573
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.4280
_cell_measurement_theta_min      4.0420
_cell_volume                     9143.36(18)
_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, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
  1 omega  -33.00   70.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7064  -57.0000    0.0000 103

  2 omega    2.00   98.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7064 -125.0000  -60.0000 96

  3 omega   46.00  109.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -94.0000   60.0000 63

  4 omega   38.00   67.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000    0.0000 29

  5 omega   31.00   66.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000   60.0000 35

  6 omega   32.00   66.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000   30.0000 34

  7 omega   35.00   61.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000  120.0000 26

  8 omega   77.00  149.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   61.0000    0.0000 72

  9 omega   28.00  141.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -77.0000 -150.0000 113

 10 omega   29.00   66.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -30.0000   90.0000 37

 11 omega   11.00  115.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7064   57.0000 -120.0000 104

 12 omega   11.00  115.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7064   57.0000  -30.0000 104

 13 omega   11.00  115.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7064   57.0000  120.0000 104

 14 omega   46.00  158.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   15.0000  -60.0000 112

 15 omega   76.00  158.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   30.0000   90.0000 82

 16 omega   32.00   77.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800  -45.0000  -30.0000 45

 17 omega   79.00  116.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   45.0000  -30.0000 37

 18 omega   73.00  158.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   77.0000   90.0000 85

 19 omega   76.00  158.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.9800   30.0000 -180.0000 82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0212162000
_diffrn_orient_matrix_UB_12      -0.0181408000
_diffrn_orient_matrix_UB_13      -0.0485154000
_diffrn_orient_matrix_UB_21      -0.0402841000
_diffrn_orient_matrix_UB_22      0.0744851000
_diffrn_orient_matrix_UB_23      -0.0248913000
_diffrn_orient_matrix_UB_31      0.0321210000
_diffrn_orient_matrix_UB_32      0.1054448000
_diffrn_orient_matrix_UB_33      0.0092736000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            69695
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.575
_diffrn_reflns_theta_min         4.066
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.882
_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            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       plate
_exptl_crystal_F_000             3544
_exptl_crystal_size_max          0.2048
_exptl_crystal_size_mid          0.1829
_exptl_crystal_size_min          0.129
_refine_diff_density_max         2.001
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1089
_refine_ls_number_reflns         18140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0515
_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^)+(0.0810P)^2^+6.8790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1492
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15696
_reflns_number_total             18140
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            4b.cif
_cod_data_source_block           fu42
_cod_original_cell_volume        9143.37(19)
_cod_database_code               4088445
_chemical_oxdiff_formula         'C112 H130 N4 Ni2'
_reflns_odcompleteness_completeness 99.69
_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. Uiso/Uaniso restraints and constraints
Uanis(C56) = Uanis(C56A)
3. Others
 Fixed Sof: H55A(0.65072) H55B(0.65072) H55C(0.34928) H55D(0.34928)
 C56(0.65072) H56A(0.65072) H56B(0.65072) H56C(0.65072) C56A(0.34928)
 H56D(0.34928) H56E(0.34928) H56F(0.34928)
4.a Ternary CH refined with riding coordinates:
 C6(H6), C9(H9), C62(H62), C65(H65)
4.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C28(H28A,H28B), C39(H39A,H39B), C47(H47A,H47B), C55(H55A,
 H55B), C55(H55C,H55D), C77(H77A,H77B), C87(H87A,H87B), C95(H95A,H95B),
 C103(H10D,H10E), C111(H11D,H11E)
4.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C21(H21), C22(H22), C25(H25), C26(H26), C30(H30),
 C31(H31), C34(H34), C35(H35), C37(H37), C38(H38), C42(H42), C43(H43), C45(H45),
  C46(H46), C50(H50), C51(H51), C53(H53), C54(H54), C74(H74), C75(H75),
 C79(H79), C80(H80), C82(H82), C83(H83), C85(H85), C86(H86), C90(H90), C91(H91),
  C93(H93), C94(H94), C98(H98), C99(H99), C101(H101), C102(H102), C106(H106),
 C107(H107), C109(H109), C110(H110)
4.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,
 H10B,H10C), C11(H11A,H11B,H11C), C24(H24A,H24B,H24C), C29(H29A,H29B,H29C),
 C40(H40A,H40B,H40C), C48(H48A,H48B,H48C), C56(H56A,H56B,H56C), C60(H60A,H60B,
 H60C), C61(H61A,H61B,H61C), C63(H63A,H63B,H63C), C64(H64A,H64B,H64C), C66(H66A,
 H66B,H66C), C67(H67A,H67B,H67C), C78(H78A,H78B,H78C), C88(H88A,H88B,H88C),
 C96(H96A,H96B,H96C), C104(H10F,H10G,H10H), C112(H11F,H11G,H11H), C56A(H56D,
 H56E,H56F)
;
_shelx_res_checksum              94743
_shelx_hkl_checksum              5156
_shelx_shelxl_version_number     2014/7
_olex2_submission_original_sample_id FU42
_olex2_submission_special_instructions 'No special instructions were received'