#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:55:58 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178730 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/41/4084101.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4084101
loop_
_publ_author_name
'Wei, Yingfei'
'Petronilho, Ana'
'Mueller-Bunz, Helge'
'Albrecht, Martin'
_publ_section_title
;
 Mesoionic Triazolylidene Nickel Complexes: Synthesis, Ligand Lability,
 and Catalytic C--C Bond Formation Activity
;
_journal_issue                   20
_journal_name_full               Organometallics
_journal_page_first              5834
_journal_paper_doi               10.1021/om500593s
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety         'C26 H34 I2 N6 Ni'
_chemical_formula_sum            'C26 H34 I2 N6 Ni'
_chemical_formula_weight         743.10
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.545(1)
_cell_angle_beta                 89.782(2)
_cell_angle_gamma                64.877(2)
_cell_formula_units_Z            1
_cell_length_a                   8.7847(2)
_cell_length_b                   9.5663(2)
_cell_length_c                   9.6180(2)
_cell_measurement_reflns_used    13008
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.4200
_cell_measurement_theta_min      3.5970
_cell_volume                     711.05(3)
_computing_cell_refinement
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_data_collection
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_data_reduction
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3196
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18917
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         29.45
_diffrn_reflns_theta_min         3.20
_exptl_absorpt_coefficient_mu    2.879
_exptl_absorpt_correction_T_max  0.729
_exptl_absorpt_correction_T_min  0.613
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
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) 
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             366
_exptl_crystal_size_max          0.2439
_exptl_crystal_size_mid          0.1845
_exptl_crystal_size_min          0.1457
_refine_diff_density_max         0.744
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.0014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0193
_refine_ls_R_factor_gt           0.0173
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0124P)²+0.4875P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0367
_refine_ls_wR_factor_ref         0.0378
_reflns_number_gt                3426
_reflns_number_total             3616
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om500593s_si_002.cif
_cod_data_source_block           alb216(6a)
_cod_database_code               4084101
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ni1 Ni 0.0000 1.0000 0.0000 0.01247(6) Uani 1 2 d S
I1 I -0.221599(13) 0.928849(12) 0.116447(12) 0.02087(5) Uani 1 1 d .
C1 C 0.15177(19) 0.77899(18) 0.04166(17) 0.0152(3) Uani 1 1 d .
C2 C 0.1814(2) 0.65516(18) -0.02606(17) 0.0156(3) Uani 1 1 d .
C8 C 0.1010(2) 0.65988(19) -0.16131(17) 0.0176(3) Uani 1 1 d .
C9 C 0.0610(2) 0.7913(2) -0.27527(19) 0.0233(4) Uani 1 1 d .
H9 H 0.0896 0.8742 -0.2653 0.028 Uiso 1 1 calc R
C10 C -0.0203(3) 0.8022(2) -0.4033(2) 0.0288(4) Uani 1 1 d .
H10 H -0.0466 0.8923 -0.4804 0.035 Uiso 1 1 calc R
C11 C -0.0635(2) 0.6824(2) -0.4198(2) 0.0275(4) Uani 1 1 d .
H11 H -0.1205 0.6907 -0.5071 0.033 Uiso 1 1 calc R
C12 C -0.0226(2) 0.5508(2) -0.3073(2) 0.0254(4) Uani 1 1 d .
H12 H -0.0504 0.4677 -0.3181 0.030 Uiso 1 1 calc R
C13 C 0.0585(2) 0.5391(2) -0.17931(19) 0.0210(3) Uani 1 1 d .
H13 H 0.0855 0.4483 -0.1029 0.025 Uiso 1 1 calc R
N1 N 0.26003(17) 0.70283(15) 0.16362(15) 0.0178(3) Uani 1 1 d .
C3 C 0.2807(2) 0.7734(2) 0.27979(19) 0.0224(3) Uani 1 1 d .
H3A H 0.2747 0.7076 0.3725 0.027 Uiso 1 1 calc R
H3B H 0.1865 0.8807 0.2673 0.027 Uiso 1 1 calc R
C4 C 0.4463(2) 0.7858(2) 0.2833(2) 0.0267(4) Uani 1 1 d .
H4A H 0.4555 0.8462 0.1887 0.032 Uiso 1 1 calc R
H4B H 0.5407 0.6779 0.3018 0.032 Uiso 1 1 calc R
C5 C 0.4619(3) 0.8682(2) 0.3984(2) 0.0310(4) Uani 1 1 d .
H5A H 0.5660 0.8843 0.3891 0.037 Uiso 1 1 calc R
H5B H 0.3647 0.9743 0.3815 0.037 Uiso 1 1 calc R
C6 C 0.4676(4) 0.7771(3) 0.5493(2) 0.0516(7) Uani 1 1 d .
H6A H 0.3626 0.7651 0.5611 0.077 Uiso 1 1 calc R
H6B H 0.4803 0.8352 0.6174 0.077 Uiso 1 1 calc R
H6C H 0.5638 0.6719 0.5673 0.077 Uiso 1 1 calc R
N2 N 0.35355(18) 0.54774(16) 0.17848(16) 0.0215(3) Uani 1 1 d .
N3 N 0.30383(17) 0.52036(15) 0.06235(15) 0.0185(3) Uani 1 1 d .
C7 C 0.3827(2) 0.35615(19) 0.0458(2) 0.0250(4) Uani 1 1 d .
H7A H 0.4963 0.3005 0.0969 0.038 Uiso 1 1 calc R
H7B H 0.3905 0.3567 -0.0560 0.038 Uiso 1 1 calc R
H7C H 0.3140 0.3017 0.0853 0.038 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 Ni1 C1 180.0 . 2_575
C1 Ni1 I1 91.05(4) . 2_575
C1 Ni1 I1 88.95(4) 2_575 2_575
C1 Ni1 I1 88.95(4) . .
C1 Ni1 I1 91.05(4) 2_575 .
I1 Ni1 I1 180.0 2_575 .
N1 C1 C2 102.40(13) . .
N1 C1 Ni1 123.03(11) . .
C2 C1 Ni1 134.50(12) . .
N3 C2 C1 105.99(14) . .
N3 C2 C8 124.86(14) . .
C1 C2 C8 129.15(14) . .
C9 C8 C13 118.54(16) . .
C9 C8 C2 118.96(14) . .
C13 C8 C2 122.47(15) . .
C10 C9 C8 120.49(16) . .
C10 C9 H9 119.8 . .
C8 C9 H9 119.8 . .
C9 C10 C11 120.57(17) . .
C9 C10 H10 119.7 . .
C11 C10 H10 119.7 . .
C12 C11 C10 119.16(17) . .
C12 C11 H11 120.4 . .
C10 C11 H11 120.4 . .
C11 C12 C13 120.59(16) . .
C11 C12 H12 119.7 . .
C13 C12 H12 119.7 . .
C12 C13 C8 120.63(16) . .
C12 C13 H13 119.7 . .
C8 C13 H13 119.7 . .
N2 N1 C1 115.54(13) . .
N2 N1 C3 117.49(14) . .
C1 N1 C3 126.96(13) . .
N1 C3 C4 112.42(14) . .
N1 C3 H3A 109.1 . .
C4 C3 H3A 109.1 . .
N1 C3 H3B 109.1 . .
C4 C3 H3B 109.1 . .
H3A C3 H3B 107.9 . .
C3 C4 C5 112.00(15) . .
C3 C4 H4A 109.2 . .
C5 C4 H4A 109.2 . .
C3 C4 H4B 109.2 . .
C5 C4 H4B 109.2 . .
H4A C4 H4B 107.9 . .
C6 C5 C4 113.80(18) . .
C6 C5 H5A 108.8 . .
C4 C5 H5A 108.8 . .
C6 C5 H5B 108.8 . .
C4 C5 H5B 108.8 . .
H5A C5 H5B 107.7 . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
N3 N2 N1 103.18(13) . .
N2 N3 C2 112.89(13) . .
N2 N3 C7 117.27(14) . .
C2 N3 C7 129.84(15) . .
N3 C7 H7A 109.5 . .
N3 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
N3 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 C1 1.9113(15) .
Ni1 C1 1.9113(15) 2_575
Ni1 I1 2.50733(11) 2_575
Ni1 I1 2.50737(11) .
C1 N1 1.365(2) .
C1 C2 1.402(2) .
C2 N3 1.378(2) .
C2 C8 1.465(2) .
C8 C9 1.393(2) .
C8 C13 1.399(2) .
C9 C10 1.388(3) .
C9 H9 0.9500 .
C10 C11 1.390(3) .
C10 H10 0.9500 .
C11 C12 1.384(3) .
C11 H11 0.9500 .
C12 C13 1.384(3) .
C12 H12 0.9500 .
C13 H13 0.9500 .
N1 N2 1.3308(19) .
N1 C3 1.472(2) .
C3 C4 1.510(2) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.528(3) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.512(3) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
N2 N3 1.317(2) .
N3 C7 1.468(2) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
I1 Ni1 C1 N1 87.98(12) 2_575
I1 Ni1 C1 N1 -92.03(12) .
I1 Ni1 C1 C2 -95.61(16) 2_575
I1 Ni1 C1 C2 84.39(16) .
N1 C1 C2 N3 -0.33(16) .
Ni1 C1 C2 N3 -177.26(12) .
N1 C1 C2 C8 178.69(15) .
Ni1 C1 C2 C8 1.8(3) .
N3 C2 C8 C9 -143.23(16) .
C1 C2 C8 C9 37.9(2) .
N3 C2 C8 C13 38.6(2) .
C1 C2 C8 C13 -140.28(17) .
C13 C8 C9 C10 0.4(3) .
C2 C8 C9 C10 -177.82(16) .
C8 C9 C10 C11 0.2(3) .
C9 C10 C11 C12 -0.8(3) .
C10 C11 C12 C13 0.8(3) .
C11 C12 C13 C8 -0.2(3) .
C9 C8 C13 C12 -0.4(2) .
C2 C8 C13 C12 177.77(15) .
C2 C1 N1 N2 0.58(18) .
Ni1 C1 N1 N2 177.97(11) .
C2 C1 N1 C3 -178.06(15) .
Ni1 C1 N1 C3 -0.7(2) .
N2 N1 C3 C4 72.49(19) .
C1 N1 C3 C4 -108.89(18) .
N1 C3 C4 C5 176.56(15) .
C3 C4 C5 C6 64.8(2) .
C1 N1 N2 N3 -0.58(18) .
C3 N1 N2 N3 178.20(13) .
N1 N2 N3 C2 0.32(17) .
N1 N2 N3 C7 -179.29(13) .
C1 C2 N3 N2 0.02(18) .
C8 C2 N3 N2 -179.06(14) .
C1 C2 N3 C7 179.56(15) .
C8 C2 N3 C7 0.5(3) .
