#------------------------------------------------------------------------------
#$Date: 2017-07-11 14:26:40 +0300 (Tue, 11 Jul 2017) $
#$Revision: 198632 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/56/4065650.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_4065650
loop_
_publ_author_name
'Jean-Baptiste dit Dominique, François'
'Gornitzka, Heinz'
'Hemmert, Catherine'
_publ_section_title
;
 Chiral Variation of a Hybrid Bis(carbene-amido) Ligand System
;
_journal_issue                   13
_journal_name_full               Organometallics
_journal_page_first              2868
_journal_paper_doi               10.1021/om100048d
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C29 H36 N6 Ni O4'
_chemical_formula_weight         591.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.3030(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.4796(4)
_cell_length_b                   18.1846(4)
_cell_length_c                   10.6625(2)
_cell_measurement_reflns_used    7520
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      30.29
_cell_measurement_theta_min      2.38
_cell_volume                     2908.36(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      193(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10994
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         5.11
_exptl_absorpt_coefficient_mu    0.712
_exptl_absorpt_correction_T_max  0.8149
_exptl_absorpt_correction_T_min  0.7639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2956
_refine_ls_number_restraints     53
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0254P)²+3.2861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0736
_reflns_number_gt                2735
_reflns_number_total             2956
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100048d_si_002.cif
_cod_data_source_block           15
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi-scans' was replaced
with the value 'multi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4065650
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.0000 0.267556(14) 0.7500 0.02578(10) Uani 1 2 d S . .
C1 C 0.07126(11) 0.33551(8) 0.68725(15) 0.0282(3) Uani 1 1 d . A .
N1 N 0.10400(9) 0.40420(7) 0.71812(13) 0.0284(3) Uani 1 1 d . . .
N3 N 0.08232(10) 0.19179(7) 0.72441(13) 0.0299(3) Uani 1 1 d . A .
C2 C 0.15381(12) 0.42753(10) 0.63403(18) 0.0382(4) Uani 1 1 d . . .
H2 H 0.1834 0.4734 0.6360 0.046 Uiso 1 1 calc R . .
C3 C 0.15207(14) 0.37252(10) 0.54896(19) 0.0442(5) Uani 1 1 d . A .
H3 H 0.1802 0.3721 0.4792 0.053 Uiso 1 1 calc R . .
C4 C 0.08051(11) 0.45309(9) 0.81364(16) 0.0310(3) Uani 1 1 d . . .
H4A H 0.1317 0.4855 0.8517 0.037 Uiso 1 1 calc R . .
H4B H 0.0668 0.4235 0.8842 0.037 Uiso 1 1 calc R . .
C5 C 0.0000 0.49967(13) 0.7500 0.0350(5) Uani 1 2 d S . .
H5A H -0.0157 0.5317 0.8161 0.042 Uiso 0.50 1 calc PR . .
H5B H 0.0157 0.5317 0.6839 0.042 Uiso 0.50 1 calc PR . .
N2 N 0.10157(11) 0.31677(8) 0.58253(14) 0.0371(3) Uani 1 1 d DU . .
C6 C 0.0759(2) 0.24346(13) 0.5173(2) 0.0304(6) Uani 0.800(5) 1 d PDU A 1
H6 H 0.0095 0.2388 0.4929 0.037 Uiso 0.800(5) 1 calc PR A 1
C7 C 0.11080(18) 0.23565(13) 0.3974(2) 0.0423(7) Uani 0.800(5) 1 d PDU A 1
H7A H 0.0863 0.2751 0.3362 0.063 Uiso 0.800(5) 1 calc PR A 1
H7B H 0.0927 0.1879 0.3568 0.063 Uiso 0.800(5) 1 calc PR A 1
H7C H 0.1760 0.2390 0.4214 0.063 Uiso 0.800(5) 1 calc PR A 1
C8 C 0.11617(13) 0.18506(9) 0.62301(16) 0.0344(4) Uani 1 1 d DU . .
C6' C 0.1207(8) 0.2472(5) 0.5310(9) 0.033(2) Uani 0.200(5) 1 d PDU A 2
H6' H 0.1770 0.2475 0.5009 0.039 Uiso 0.200(5) 1 calc PR A 2
C7' C 0.0385(7) 0.2390(6) 0.4231(9) 0.044(3) Uani 0.200(5) 1 d PDU A 2
H7'1 H -0.0142 0.2401 0.4584 0.066 Uiso 0.200(5) 1 calc PR A 2
H7'2 H 0.0407 0.1920 0.3789 0.066 Uiso 0.200(5) 1 calc PR A 2
H7'3 H 0.0353 0.2794 0.3613 0.066 Uiso 0.200(5) 1 calc PR A 2
O1 O 0.17140(9) 0.13880(7) 0.60415(12) 0.0421(3) Uani 1 1 d . A .
C9 C 0.11282(11) 0.14384(9) 0.83245(16) 0.0301(3) Uani 1 1 d . . .
C10 C 0.14508(13) 0.17450(11) 0.95403(17) 0.0400(4) Uani 1 1 d . A .
H10 H 0.1484 0.2265 0.9631 0.048 Uiso 1 1 calc R . .
C11 C 0.17269(15) 0.13017(14) 1.0631(2) 0.0545(6) Uani 1 1 d . . .
H11 H 0.1947 0.1519 1.1460 0.065 Uiso 1 1 calc R A .
C12 C 0.16804(15) 0.05471(14) 1.0506(2) 0.0584(6) Uani 1 1 d . A .
H12 H 0.1864 0.0242 1.1248 0.070 Uiso 1 1 calc R . .
C13 C 0.13663(14) 0.02366(12) 0.9298(2) 0.0533(6) Uani 1 1 d . . .
H13 H 0.1340 -0.0284 0.9213 0.064 Uiso 1 1 calc R A .
C14 C 0.10874(13) 0.06755(10) 0.8201(2) 0.0406(4) Uani 1 1 d . A .
H14 H 0.0871 0.0456 0.7375 0.049 Uiso 1 1 calc R . .
C15 C 0.15015(17) 0.35115(15) 0.1363(2) 0.0623(6) Uani 1 1 d . . .
H15A H 0.1791 0.3632 0.0669 0.093 Uiso 1 1 calc R . .
H15B H 0.0853 0.3527 0.1023 0.093 Uiso 1 1 calc R . .
H15C H 0.1682 0.3018 0.1694 0.093 Uiso 1 1 calc R . .
O2 O 0.17561(10) 0.40238(8) 0.23654(16) 0.0543(4) Uani 1 1 d . . .
H2A H 0.2285 0.3942 0.2774 0.082 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
C1 Ni1 C1 98.11(9) 2_556 .
C1 Ni1 N3 167.63(6) 2_556 .
C1 Ni1 N3 87.33(6) . .
C1 Ni1 N3 87.33(6) 2_556 2_556
C1 Ni1 N3 167.63(6) . 2_556
N3 Ni1 N3 89.57(8) . 2_556
N2 C1 N1 104.26(14) . .
N2 C1 Ni1 118.60(12) . .
N1 C1 Ni1 137.14(12) . .
C1 N1 C2 111.03(14) . .
C1 N1 C4 125.83(13) . .
C2 N1 C4 122.54(14) . .
C8 N3 C9 119.04(14) . .
C8 N3 Ni1 126.07(11) . .
C9 N3 Ni1 114.67(10) . .
C3 C2 N1 106.67(16) . .
C3 C2 H2 126.7 . .
N1 C2 H2 126.7 . .
C2 C3 N2 106.82(15) . .
C2 C3 H3 126.6 . .
N2 C3 H3 126.6 . .
N1 C4 C5 110.17(13) . .
N1 C4 H4A 109.6 . .
C5 C4 H4A 109.6 . .
N1 C4 H4B 109.6 . .
C5 C4 H4B 109.6 . .
H4A C4 H4B 108.1 . .
C4 C5 C4 112.31(19) 2_556 .
C4 C5 H5A 109.1 2_556 .
C4 C5 H5A 109.1 . .
C4 C5 H5B 109.1 2_556 .
C4 C5 H5B 109.1 . .
H5A C5 H5B 107.9 . .
C1 N2 C3 111.22(14) . .
C1 N2 C6' 132.9(4) . .
C3 N2 C6' 111.3(5) . .
C1 N2 C6 119.67(16) . .
C3 N2 C6 129.08(17) . .
C6' N2 C6 26.4(4) . .
N2 C6 C7 111.3(2) . .
N2 C6 C8 104.79(18) . .
C7 C6 C8 112.6(2) . .
N2 C6 H6 109.4 . .
C7 C6 H6 109.4 . .
C8 C6 H6 109.4 . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
O1 C8 N3 128.34(16) . .
O1 C8 C6' 104.8(4) . .
N3 C8 C6' 123.7(4) . .
O1 C8 C6 120.55(17) . .
N3 C8 C6 111.09(16) . .
C6' C8 C6 25.4(4) . .
N2 C6' C7' 99.5(7) . .
N2 C6' C8 111.3(6) . .
C7' C6' C8 104.9(8) . .
N2 C6' H6' 113.4 . .
C7' C6' H6' 113.4 . .
C8 C6' H6' 113.4 . .
C6' C7' H7'1 109.5 . .
C6' C7' H7'2 109.5 . .
H7'1 C7' H7'2 109.5 . .
C6' C7' H7'3 109.5 . .
H7'1 C7' H7'3 109.5 . .
H7'2 C7' H7'3 109.5 . .
C10 C9 C14 119.08(16) . .
C10 C9 N3 118.66(15) . .
C14 C9 N3 122.23(16) . .
C9 C10 C11 120.91(19) . .
C9 C10 H10 119.5 . .
C11 C10 H10 119.5 . .
C12 C11 C10 119.8(2) . .
C12 C11 H11 120.1 . .
C10 C11 H11 120.1 . .
C11 C12 C13 119.69(19) . .
C11 C12 H12 120.2 . .
C13 C12 H12 120.2 . .
C12 C13 C14 120.9(2) . .
C12 C13 H13 119.6 . .
C14 C13 H13 119.6 . .
C13 C14 C9 119.6(2) . .
C13 C14 H14 120.2 . .
C9 C14 H14 120.2 . .
O2 C15 H15A 109.5 . .
O2 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
O2 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C15 O2 H2A 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 1.8858(16) 2_556
Ni1 C1 1.8858(16) .
Ni1 N3 1.9412(13) .
Ni1 N3 1.9413(13) 2_556
C1 N2 1.357(2) .
C1 N1 1.358(2) .
N1 C2 1.386(2) .
N1 C4 1.464(2) .
N3 C8 1.318(2) .
N3 C9 1.429(2) .
C2 C3 1.346(3) .
C2 H2 0.9500 .
C3 N2 1.380(2) .
C3 H3 0.9500 .
C4 C5 1.521(2) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C4 1.521(2) 2_556
C5 H5A 0.9900 .
C5 H5B 0.9900 .
N2 C6' 1.438(9) .
N2 C6 1.511(3) .
C6 C7 1.513(3) .
C6 C8 1.562(3) .
C6 H6 1.0000 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 O1 1.251(2) .
C8 C6' 1.510(10) .
C6' C7' 1.498(12) .
C6' H6' 1.0000 .
C7' H7'1 0.9800 .
C7' H7'2 0.9800 .
C7' H7'3 0.9800 .
C9 C10 1.386(3) .
C9 C14 1.394(2) .
C10 C11 1.393(3) .
C10 H10 0.9500 .
C11 C12 1.379(3) .
C11 H11 0.9500 .
C12 C13 1.381(4) .
C12 H12 0.9500 .
C13 C14 1.393(3) .
C13 H13 0.9500 .
C14 H14 0.9500 .
C15 O2 1.399(3) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
O2 H2A 0.8400 .
