#------------------------------------------------------------------------------
#$Date: 2017-07-11 14:26:40 +0300 (Tue, 11 Jul 2017) $
#$Revision: 198632 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/56/4065648.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_4065648
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            'C27 H32 N6 Ni O4'
_chemical_formula_weight         563.30
_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                 112.797(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.7743(10)
_cell_length_b                   16.0012(10)
_cell_length_c                   12.3916(9)
_cell_measurement_reflns_used    1177
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      18.51
_cell_measurement_theta_min      2.55
_cell_volume                     2700.6(3)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0989
_diffrn_reflns_av_sigmaI/netI    0.0878
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11452
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         5.13
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  0.9276
_exptl_absorpt_correction_T_min  0.7153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0443
_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)+(0.0269P)²+1.6424P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0884
_reflns_number_gt                1688
_reflns_number_total             2453
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100048d_si_002.cif
_cod_data_source_block           5
_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               4065648
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
Ni1 Ni 0.5000 0.35690(4) 0.2500 0.01550(18) Uani 1 2 d S
N1 N 0.59546(18) 0.27031(14) 0.2641(2) 0.0161(6) Uani 1 1 d .
N2 N 0.63049(18) 0.40944(15) 0.1517(2) 0.0165(6) Uani 1 1 d .
N3 N 0.62003(18) 0.51171(15) 0.2573(2) 0.0184(6) Uani 1 1 d .
C1 C 0.5858(2) 0.43255(18) 0.2244(2) 0.0162(7) Uani 1 1 d .
C2 C 0.6834(2) 0.5366(2) 0.2050(3) 0.0223(8) Uani 1 1 d .
H2 H 0.7157 0.5890 0.2141 0.027 Uiso 1 1 calc R
C3 C 0.6902(2) 0.47195(19) 0.1389(3) 0.0216(8) Uani 1 1 d .
H3 H 0.7284 0.4697 0.0925 0.026 Uiso 1 1 calc R
C4 C 0.5865(2) 0.56702(19) 0.3275(3) 0.0206(8) Uani 1 1 d .
H4A H 0.6410 0.6042 0.3749 0.025 Uiso 1 1 calc R
H4B H 0.5668 0.5334 0.3818 0.025 Uiso 1 1 calc R
C5 C 0.5000 0.6195(3) 0.2500 0.0225(11) Uani 1 2 d S
H5A H 0.4784 0.6560 0.3001 0.027 Uiso 0.50 1 calc PR
H5B H 0.5216 0.6560 0.1999 0.027 Uiso 0.50 1 calc PR
C6 C 0.6192(2) 0.32635(18) 0.0976(3) 0.0176(7) Uani 1 1 d .
H6A H 0.6666 0.3202 0.0595 0.021 Uiso 1 1 calc R
H6B H 0.5522 0.3209 0.0365 0.021 Uiso 1 1 calc R
C7 C 0.6366(2) 0.25683(19) 0.1887(3) 0.0185(7) Uani 1 1 d .
O1 O 0.68835(17) 0.19620(14) 0.18346(18) 0.0274(6) Uani 1 1 d .
C8 C 0.6139(2) 0.2164(2) 0.3615(3) 0.0184(7) Uani 1 1 d .
C9 C 0.6302(2) 0.2535(2) 0.4693(3) 0.0253(8) Uani 1 1 d .
H9 H 0.6313 0.3127 0.4754 0.030 Uiso 1 1 calc R
C10 C 0.6448(3) 0.2057(3) 0.5670(3) 0.0348(9) Uani 1 1 d .
H10 H 0.6557 0.2321 0.6396 0.042 Uiso 1 1 calc R
C11 C 0.6438(3) 0.1198(3) 0.5603(3) 0.0421(11) Uani 1 1 d .
H11 H 0.6536 0.0869 0.6276 0.050 Uiso 1 1 calc R
C12 C 0.6283(3) 0.0822(2) 0.4543(3) 0.0393(10) Uani 1 1 d .
H12 H 0.6279 0.0229 0.4495 0.047 Uiso 1 1 calc R
C13 C 0.6133(2) 0.1294(2) 0.3541(3) 0.0279(8) Uani 1 1 d .
H13 H 0.6028 0.1027 0.2818 0.033 Uiso 1 1 calc R
C15 C 0.6112(3) 0.1643(3) 0.8849(3) 0.0537(12) Uani 1 1 d .
H15A H 0.5517 0.1604 0.9017 0.080 Uiso 1 1 calc R
H15B H 0.6039 0.1291 0.8174 0.080 Uiso 1 1 calc R
H15C H 0.6213 0.2225 0.8675 0.080 Uiso 1 1 calc R
O2 O 0.69245(17) 0.13702(16) 0.98294(18) 0.0343(6) Uani 1 1 d .
H2A H 0.6899 0.1578 1.0440 0.051 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 99.17(18) . 2_655
C1 Ni1 N1 87.73(11) . .
C1 Ni1 N1 165.37(11) 2_655 .
C1 Ni1 N1 165.37(11) . 2_655
C1 Ni1 N1 87.73(11) 2_655 2_655
N1 Ni1 N1 88.61(14) . 2_655
C7 N1 C8 121.0(3) . .
C7 N1 Ni1 125.1(2) . .
C8 N1 Ni1 113.85(18) . .
C1 N2 C3 112.0(2) . .
C1 N2 C6 123.4(2) . .
C3 N2 C6 124.5(2) . .
C1 N3 C2 111.4(2) . .
C1 N3 C4 124.7(2) . .
C2 N3 C4 123.5(3) . .
N2 C1 N3 103.4(2) . .
N2 C1 Ni1 118.2(2) . .
N3 C1 Ni1 138.4(2) . .
C3 C2 N3 106.6(3) . .
C2 C3 N2 106.5(3) . .
N3 C4 C5 110.8(2) . .
C4 C5 C4 112.9(4) 2_655 .
N2 C6 C7 111.3(2) . .
O1 C7 N1 128.6(3) . .
O1 C7 C6 117.1(3) . .
N1 C7 C6 114.3(3) . .
C13 C8 C9 118.8(3) . .
C13 C8 N1 123.8(3) . .
C9 C8 N1 117.4(3) . .
C10 C9 C8 121.1(3) . .
C11 C10 C9 120.5(3) . .
C10 C11 C12 119.2(3) . .
C11 C12 C13 121.3(4) . .
C8 C13 C12 119.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 C1 1.867(3) .
Ni1 C1 1.867(3) 2_655
Ni1 N1 1.936(2) .
Ni1 N1 1.936(2) 2_655
N1 C7 1.315(4) .
N1 C8 1.421(4) .
N2 C1 1.358(3) .
N2 C3 1.383(4) .
N2 C6 1.469(4) .
N3 C1 1.366(4) .
N3 C2 1.388(4) .
N3 C4 1.456(4) .
C2 C3 1.348(4) .
C4 C5 1.520(4) .
C5 C4 1.520(4) 2_655
C6 C7 1.534(4) .
C7 O1 1.252(3) .
C8 C13 1.395(4) .
C8 C9 1.395(4) .
C9 C10 1.377(4) .
C10 C11 1.376(5) .
C11 C12 1.380(5) .
C12 C13 1.397(4) .
C15 O2 1.406(4) .
