#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:06:20 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179467 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/64/4336429.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_4336429
loop_
_publ_author_name
'Alexander G. Tskhovrebov'
'Euro Solari'
'Rosario Scopelliti'
'Kay Severin'
_publ_section_title
;
 Insertion of Zerovalent Nickel into the N-N Bond of
 N-Heterocyclic-Carbene-Activated N2O
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11688
_journal_page_last               11690
_journal_paper_doi               10.1021/ic401524w
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C18 H32 N8 Ni2 O2'
_chemical_formula_sum            'C18 H32 N8 Ni2 O2'
_chemical_formula_weight         509.94
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-04-23 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.63(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.137(3)
_cell_length_b                   9.3930(16)
_cell_length_c                   13.106(3)
_cell_measurement_reflns_used    111
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22
_cell_measurement_theta_min      3
_cell_volume                     1212.8(5)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs, 1990-2000)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1155
_diffrn_reflns_av_sigmaI/netI    0.0664
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15233
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.16
_exptl_absorpt_coefficient_mu    1.581
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008, Bruker AXS, 2008'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         2.041
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.233
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.233
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0782
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0325P)²+13.8362P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2002
_refine_ls_wR_factor_ref         0.2159
_reflns_number_gt                2174
_reflns_number_total             2770
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic401524w_si_002.cif
_cod_data_source_block           al475
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4336429
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.62763(8) 0.06549(8) 0.50337(6) 0.0183(3) Uani 1 1 d .
O1 O 0.8676(6) 0.2267(7) 0.5580(5) 0.0453(15) Uani 1 1 d .
N1 N 0.2520(5) 0.2182(6) 0.3197(4) 0.0229(12) Uani 1 1 d .
N2 N 0.4380(5) 0.2024(6) 0.2611(4) 0.0197(11) Uani 1 1 d .
N3 N 0.4422(5) 0.0907(6) 0.4288(4) 0.0202(11) Uani 1 1 d .
N4 N 0.7710(5) 0.1540(6) 0.5266(4) 0.0227(11) Uani 1 1 d .
C1 C 0.3844(6) 0.1634(6) 0.3457(5) 0.0186(12) Uani 1 1 d .
C2 C 0.2282(7) 0.2851(8) 0.2219(5) 0.0263(14) Uani 1 1 d .
H2 H 0.1457 0.3291 0.1864 0.032 Uiso 1 1 calc R
C3 C 0.3426(7) 0.2765(7) 0.1865(5) 0.0254(14) Uani 1 1 d .
H3 H 0.3555 0.3142 0.1222 0.030 Uiso 1 1 calc R
C4 C 0.1549(6) 0.2089(7) 0.3863(6) 0.0231(13) Uani 1 1 d .
H4 H 0.2011 0.1587 0.4524 0.028 Uiso 1 1 calc R
C5 C 0.1148(8) 0.3576(8) 0.4170(7) 0.0351(17) Uani 1 1 d .
H5A H 0.1963 0.4093 0.4533 0.053 Uiso 1 1 calc R
H5B H 0.0526 0.3485 0.4637 0.053 Uiso 1 1 calc R
H5C H 0.0698 0.4099 0.3537 0.053 Uiso 1 1 calc R
C6 C 0.0319(7) 0.1190(9) 0.3329(6) 0.0335(16) Uani 1 1 d .
H6A H -0.0175 0.1673 0.2690 0.050 Uiso 1 1 calc R
H6B H -0.0281 0.1067 0.3809 0.050 Uiso 1 1 calc R
H6C H 0.0627 0.0256 0.3146 0.050 Uiso 1 1 calc R
C7 C 0.5768(7) 0.1670(7) 0.2505(5) 0.0237(13) Uani 1 1 d .
H7 H 0.6147 0.0937 0.3049 0.028 Uiso 1 1 calc R
C8 C 0.5735(8) 0.1017(8) 0.1429(6) 0.0331(16) Uani 1 1 d .
H8A H 0.5113 0.0203 0.1309 0.050 Uiso 1 1 calc R
H8B H 0.6648 0.0698 0.1407 0.050 Uiso 1 1 calc R
H8C H 0.5422 0.1733 0.0881 0.050 Uiso 1 1 calc R
C9 C 0.6679(7) 0.2997(8) 0.2743(6) 0.0278(15) Uani 1 1 d .
H9A H 0.6337 0.3733 0.2218 0.042 Uiso 1 1 calc R
H9B H 0.7610 0.2744 0.2719 0.042 Uiso 1 1 calc R
H9C H 0.6672 0.3359 0.3443 0.042 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'
O O 0.0106 0.0060 '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'
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
N4 Ni1 N3 138.7(3) . .
N4 Ni1 N3 134.7(3) . 3_656
N3 Ni1 N3 84.7(2) . 3_656
N4 Ni1 Ni1 169.8(2) . 3_656
N3 Ni1 Ni1 42.55(16) . 3_656
N3 Ni1 Ni1 42.12(15) 3_656 3_656
C2 N1 C1 109.7(5) . .
C2 N1 C4 125.4(5) . .
C1 N1 C4 124.9(5) . .
C3 N2 C1 110.7(5) . .
C3 N2 C7 124.4(5) . .
C1 N2 C7 124.9(5) . .
C1 N3 Ni1 133.2(4) . .
C1 N3 Ni1 129.9(4) . 3_656
Ni1 N3 Ni1 95.3(2) . 3_656
O1 N4 Ni1 168.6(6) . .
N3 C1 N2 128.3(5) . .
N3 C1 N1 127.8(6) . .
N2 C1 N1 103.9(5) . .
C3 C2 N1 108.2(6) . .
C3 C2 H2 125.9 . .
N1 C2 H2 125.9 . .
C2 C3 N2 107.5(6) . .
C2 C3 H3 126.3 . .
N2 C3 H3 126.3 . .
N1 C4 C6 110.5(6) . .
N1 C4 C5 111.0(6) . .
C6 C4 C5 112.6(6) . .
N1 C4 H4 107.5 . .
C6 C4 H4 107.5 . .
C5 C4 H4 107.5 . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C4 C6 H6A 109.5 . .
C4 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C4 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
N2 C7 C8 111.1(6) . .
N2 C7 C9 109.7(5) . .
C8 C7 C9 113.1(6) . .
N2 C7 H7 107.6 . .
C8 C7 H7 107.6 . .
C9 C7 H7 107.6 . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C7 C9 H9A 109.5 . .
C7 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C7 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N4 1.639(5) .
Ni1 N3 1.918(5) .
Ni1 N3 1.934(5) 3_656
Ni1 Ni1 2.8478(16) 3_656
O1 N4 1.185(7) .
N1 C2 1.397(9) .
N1 C1 1.402(7) .
N1 C4 1.464(8) .
N2 C3 1.390(8) .
N2 C1 1.394(8) .
N2 C7 1.483(8) .
N3 C1 1.301(8) .
N3 Ni1 1.934(5) 3_656
C2 C3 1.349(9) .
C2 H2 0.9500 .
C3 H3 0.9500 .
C4 C6 1.531(10) .
C4 C5 1.535(9) .
C4 H4 1.0000 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 C8 1.531(10) .
C7 C9 1.539(10) .
C7 H7 1.0000 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 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
_geom_torsion_site_symmetry_4
N4 Ni1 N3 C1 28.9(8) . .
N3 Ni1 N3 C1 -166.3(8) 3_656 .
Ni1 Ni1 N3 C1 -166.3(8) 3_656 .
N4 Ni1 N3 Ni1 -164.8(3) . 3_656
N3 Ni1 N3 Ni1 -0.001(1) 3_656 3_656
N3 Ni1 N4 O1 90(3) . .
N3 Ni1 N4 O1 -69(3) 3_656 .
Ni1 Ni1 N4 O1 -2(4) 3_656 .
Ni1 N3 C1 N2 27.8(10) . .
Ni1 N3 C1 N2 -134.4(6) 3_656 .
Ni1 N3 C1 N1 -153.7(5) . .
Ni1 N3 C1 N1 44.2(10) 3_656 .
C3 N2 C1 N3 178.3(6) . .
C7 N2 C1 N3 -0.3(10) . .
C3 N2 C1 N1 -0.5(7) . .
C7 N2 C1 N1 -179.1(6) . .
C2 N1 C1 N3 -177.8(6) . .
C4 N1 C1 N3 3.3(11) . .
C2 N1 C1 N2 1.0(7) . .
C4 N1 C1 N2 -177.9(6) . .
C1 N1 C2 C3 -1.2(8) . .
C4 N1 C2 C3 177.7(6) . .
N1 C2 C3 N2 0.8(8) . .
C1 N2 C3 C2 -0.2(8) . .
C7 N2 C3 C2 178.4(6) . .
C2 N1 C4 C6 65.2(9) . .
C1 N1 C4 C6 -116.1(7) . .
C2 N1 C4 C5 -60.4(9) . .
C1 N1 C4 C5 118.3(7) . .
C3 N2 C7 C8 -48.3(8) . .
C1 N2 C7 C8 130.2(6) . .
C3 N2 C7 C9 77.5(8) . .
C1 N2 C7 C9 -104.0(7) . .
