#------------------------------------------------------------------------------
#$Date: 2016-02-16 21:30:59 +0100 (mar 16 de feb de 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/24/4312451.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_4312451
loop_
_publ_author_name
'Maximilian N. Kopylovich'
'Armando J. L. Pombeiro'
'Andreas Fischer'
'Lars Kloo'
'Vadim Yu. Kukushkin'
_publ_contact_author_address
;
Department of Chemistry
St. Petersburg State University
198504 Stary Petergof
Russian Federation
;
_publ_contact_author_email       kukushkin@VK2100.spb.edu
_publ_contact_author_name        'Vadim Yu. Kukushkin'
_publ_section_title
;
 Facile Ni(II)/Ketoxime-Mediated Conversion of Organonitriles into
 Imidoylamidine Ligands. Synthesis of Imidoylamidines and Acetyl Amides
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7239
_journal_page_last               7248
_journal_paper_doi               10.1021/ic0349813
_journal_volume                  42
_journal_year                    2003
_chemical_compound_source        'Local laboratory'
_chemical_formula_moiety         'C56 H66 N6 Ni O12 '
_chemical_formula_sum            'C56 H66 N6 Ni O12'
_chemical_formula_weight         1073.884
_chemical_name_systematic
;
 ?
;
_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_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 108.2261(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.41480(10)
_cell_length_b                   13.2229(2)
_cell_length_c                   17.8389(2)
_cell_measurement_reflns_used    51145
_cell_measurement_temperature    297
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      4.29
_cell_volume                     2781.51(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.08292
_diffrn_orient_matrix_UB_12      0.00012
_diffrn_orient_matrix_UB_13      -0.01778
_diffrn_orient_matrix_UB_21      -0.01579
_diffrn_orient_matrix_UB_22      0.00649
_diffrn_orient_matrix_UB_23      0.07368
_diffrn_orient_matrix_UB_31      -0.01697
_diffrn_orient_matrix_UB_32      0.05588
_diffrn_orient_matrix_UB_33      -0.00856
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.0899
_diffrn_reflns_av_sigmaI/netI    0.0716
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18031
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         4.29
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Irregular
_refine_diff_density_max         0.872
_refine_diff_density_min         -1.143
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         5634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0781
_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
 [1.00000+0.00000exp(0.00(sinθ/λ)²)]/
   [σ²(Fo²)+0.0000+0.6400*P+(0.1600P)²+0.0000sinθ/λ]
 where P = 0.00000Fo² + 1.00000Fc²
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2158
_refine_ls_wR_factor_ref         0.2312
_reflns_number_gt                4502
_reflns_number_total             5634
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0349813si20030818_063355_7.cif
_cod_data_source_block           compound7
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_original_formula_sum        'C56 H66 N6 Ni O12 '
_cod_database_code               4312451
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 1.0000 0.5000 0.0000 0.0350(2) Uani 1 2 d S . .
N1 N 1.0312(2) 0.36244(19) 0.01439(14) 0.0437(5) Uani 1 1 d . . .
O3 O 0.0253(2) 0.21651(19) 0.26170(14) 0.0615(6) Uani 1 1 d . . .
N2 N 0.9846(2) 0.33517(18) 0.12904(14) 0.0459(6) Uani 1 1 d . . .
C10 C 0.9446(2) 0.4307(2) 0.13506(15) 0.0399(6) Uani 1 1 d . . .
O4 O 0.1147(2) 0.19963(18) 0.38960(13) 0.0612(6) Uani 1 1 d . . .
N3 N 0.9442(2) 0.50027(15) 0.08493(15) 0.0403(5) Uani 1 1 d . . .
C19 C 0.0992(2) 0.2423(2) 0.32447(17) 0.0439(6) Uani 1 1 d . . .
C1 C 1.0221(2) 0.3028(2) 0.06937(16) 0.0425(6) Uani 1 1 d . . .
C14 C 0.7412(3) 0.3170(3) 0.1825(2) 0.0579(8) Uani 1 1 d . . .
C12 C 0.7723(3) 0.4175(2) 0.17797(17) 0.0458(7) Uani 1 1 d . . .
C11 C 0.8964(3) 0.4481(2) 0.20240(17) 0.0455(6) Uani 1 1 d . . .
O2 O 0.4357(2) 0.3237(2) 0.10856(17) 0.0774(8) Uani 1 1 d . . .
C3 C 0.9422(3) 0.1338(2) 0.0262(2) 0.0563(8) Uani 1 1 d . . .
C21 C 0.2989(3) 0.2965(2) 0.3415(2) 0.0540(8) Uani 1 1 d . . .
C16 C 0.6287(3) 0.2884(3) 0.1589(2) 0.0650(9) Uani 1 1 d . . .
C17 C 0.5438(3) 0.3604(3) 0.1302(2) 0.0583(8) Uani 1 1 d . . .
C23 C 0.3690(3) 0.2895(3) 0.4184(2) 0.0628(9) Uani 1 1 d . . .
C25 C 0.4802(3) 0.2539(3) 0.4361(2) 0.0652(9) Uani 1 1 d . . .
C2 C 1.0483(3) 0.1913(2) 0.0689(2) 0.0572(8) Uani 1 1 d . . .
C20 C 0.1773(3) 0.3306(2) 0.3228(2) 0.0609(9) Uani 1 1 d . . .
C26 C 0.5212(3) 0.2237(3) 0.3765(2) 0.0616(9) Uani 1 1 d . . .
C5 C 0.8727(4) 0.0936(3) 0.0673(2) 0.0720(10) Uani 1 1 d . . .
O5 O 0.6268(3) 0.1847(3) 0.38789(19) 0.0856(9) Uani 1 1 d . . .
C15 C 0.5736(3) 0.4601(3) 0.1258(2) 0.0645(9) Uani 1 1 d . . .
C13 C 0.6864(3) 0.4878(2) 0.1490(2) 0.0554(8) Uani 1 1 d . . .
C22 C 0.3430(4) 0.2690(4) 0.2828(2) 0.0754(11) Uani 1 1 d . . .
C27 C 0.6999(4) 0.1770(4) 0.4665(3) 0.0808(12) Uani 1 1 d . . .
C4 C 0.9074(4) 0.1233(3) -0.0552(2) 0.0752(11) Uani 1 1 d . . .
C8 C 0.7716(5) 0.0465(3) 0.0275(3) 0.0871(13) Uani 1 1 d . . .
C24 C 0.4525(4) 0.2333(4) 0.2998(2) 0.0790(12) Uani 1 1 d . . .
C6 C 0.8058(5) 0.0760(4) -0.0943(3) 0.0965(16) Uani 1 1 d . . .
C7 C 0.7388(5) 0.0377(3) -0.0523(3) 0.0929(15) Uani 1 1 d . . .
O1 O 0.6359(6) -0.0096(4) -0.0852(4) 0.152(2) Uani 1 1 d . . .
C18 C 0.3469(4) 0.3914(5) 0.0722(3) 0.1024(17) Uani 1 1 d . . .
O6 O 0.1398(3) 0.5692(2) 0.24961(17) 0.0759(8) Uani 1 1 d . . .
C9 C 0.5846(13) -0.0113(8) -0.1555(9) 0.271(9) Uani 1 1 d . . .
C28 C 0.2122(5) 0.5771(5) 0.2033(3) 0.1056(18) Uani 1 1 d . . .
H1 H 1.0769 0.3192 -0.0170 0.052 Uiso 1 1 d R . .
H2 H 0.9870 0.2853 0.1733 0.055 Uiso 1 1 d R . .
H3 H 0.9155 0.5590 0.1046 0.048 Uiso 1 1 d R . .
H14 H 0.8029 0.2694 0.1975 0.069 Uiso 1 1 d R . .
H11A H 0.9495 0.4029 0.2533 0.055 Uiso 1 1 d R . .
H11B H 0.9000 0.5413 0.2106 0.055 Uiso 1 1 d R . .
H16 H 0.6091 0.2188 0.1626 0.078 Uiso 1 1 d R . .
H23 H 0.3557 0.3179 0.4658 0.075 Uiso 1 1 d R . .
H25 H 0.5196 0.2574 0.4909 0.078 Uiso 1 1 d R . .
H2A H 1.0849 0.1662 0.1258 0.069 Uiso 1 1 d R . .
H2B H 1.1006 0.1680 0.0409 0.069 Uiso 1 1 d R . .
H20A H 0.1545 0.3637 0.2744 0.073 Uiso 1 1 d R . .
H20B H 0.1746 0.3736 0.3759 0.073 Uiso 1 1 d R . .
H5 H 0.8998 0.1067 0.1296 0.086 Uiso 1 1 d R . .
H15 H 0.5214 0.5079 0.1095 0.077 Uiso 1 1 d R . .
H13 H 0.7099 0.5521 0.1397 0.066 Uiso 1 1 d R . .
H22 H 0.2895 0.2618 0.2378 0.091 Uiso 1 1 d R . .
H27A H 0.7713 0.1486 0.4671 0.097 Uiso 1 1 d R . .
H27B H 0.7120 0.2430 0.4900 0.097 Uiso 1 1 d R . .
H27C H 0.6653 0.1341 0.4959 0.097 Uiso 1 1 d R . .
H4 H 0.9545 0.1752 -0.0740 0.090 Uiso 1 1 d R . .
H8 H 0.7249 0.0200 0.0569 0.104 Uiso 1 1 d R . .
H24 H 0.4751 0.2071 0.2589 0.095 Uiso 1 1 d R . .
H6 H 0.7827 0.0705 -0.1507 0.116 Uiso 1 1 d R . .
H18A H 0.2753 0.3571 0.0596 0.123 Uiso 1 1 d R . .
H18B H 0.3569 0.4182 0.0248 0.123 Uiso 1 1 d R . .
H18C H 0.3483 0.4458 0.1082 0.123 Uiso 1 1 d R . .
H9A H 0.5133 -0.0464 -0.1713 0.325 Uiso 1 1 d R . .
H9B H 0.6353 -0.0426 -0.1796 0.325 Uiso 1 1 d R . .
H9C H 0.5729 0.0580 -0.1719 0.325 Uiso 1 1 d R . .
H28A H 0.1513 0.5808 0.1544 0.127 Uiso 1 1 d R . .
H28B H 0.2540 0.6394 0.2118 0.127 Uiso 1 1 d R . .
H28C H 0.2617 0.5222 0.2010 0.127 Uiso 1 1 d 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_radiation_wavelength
0.71073
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
_geom_angle_publ_flag
N3 Ni1 N3 180.00(6) . 3_765 ?
N3 Ni1 N1 90.23(9) . . ?
N3 Ni1 N1 89.76(9) 3_765 . ?
N3 Ni1 N1 89.77(9) . 3_765 ?
N3 Ni1 N1 90.23(9) 3_765 3_765 ?
N1 Ni1 N1 179.9990(10) . 3_765 ?
C1 N1 Ni1 129.6(2) . . ?
C1 N2 C10 124.9(2) . . ?
N3 C10 N2 121.9(2) . . ?
N3 C10 C11 121.8(2) . . ?
N2 C10 C11 116.3(2) . . ?
C10 N3 Ni1 130.4(2) . . ?
O4 C19 O3 124.4(3) . . ?
O4 C19 C20 116.7(3) . . ?
O3 C19 C20 118.9(3) . . ?
N1 C1 N2 122.4(3) . . ?
N1 C1 C2 121.4(3) . . ?
N2 C1 C2 116.1(3) . . ?
C16 C14 C12 121.1(3) . . ?
C13 C12 C14 117.8(3) . . ?
C13 C12 C11 121.4(3) . . ?
C14 C12 C11 120.8(3) . . ?
C10 C11 C12 110.4(2) . . ?
C17 O2 C18 117.5(4) . . ?
C4 C3 C5 118.0(4) . . ?
C4 C3 C2 121.1(3) . . ?
C5 C3 C2 120.9(3) . . ?
C22 C21 C23 117.5(3) . . ?
C22 C21 C20 121.4(3) . . ?
C23 C21 C20 121.1(3) . . ?
C14 C16 C17 120.2(3) . . ?
O2 C17 C15 125.6(3) . . ?
O2 C17 C16 115.2(3) . . ?
C15 C17 C16 119.2(3) . . ?
C21 C23 C25 121.3(3) . . ?
C26 C25 C23 120.1(3) . . ?
C3 C2 C1 109.9(3) . . ?
C21 C20 C19 111.4(3) . . ?
O5 C26 C24 116.9(4) . . ?
O5 C26 C25 124.5(3) . . ?
C24 C26 C25 118.6(4) . . ?
C8 C5 C3 120.8(4) . . ?
C26 O5 C27 117.6(3) . . ?
C17 C15 C13 120.1(3) . . ?
C15 C13 C12 121.6(3) . . ?
C21 C22 C24 121.6(3) . . ?
C6 C4 C3 120.6(4) . . ?
C7 C8 C5 120.2(4) . . ?
C26 C24 C22 120.8(4) . . ?
C7 C6 C4 120.1(4) . . ?
C8 C7 C6 120.3(5) . . ?
C8 C7 O1 114.8(5) . . ?
C6 C7 O1 124.9(6) . . ?
C9 O1 C7 124.3(10) . . ?
C1 N1 H1 104.9 . . ?
Ni1 N1 H1 124.6 . . ?
C1 N2 H2 117.9 . . ?
C10 N2 H2 117.2 . . ?
C10 N3 H3 104.1 . . ?
Ni1 N3 H3 125.1 . . ?
C16 C14 H14 123.2 . . ?
C12 C14 H14 115.4 . . ?
C10 C11 H11A 106.5 . . ?
C12 C11 H11A 112.3 . . ?
C10 C11 H11B 103.6 . . ?
C12 C11 H11B 107.1 . . ?
H11A C11 H11B 116.5 . . ?
C14 C16 H16 119.7 . . ?
C17 C16 H16 120.1 . . ?
C21 C23 H23 127.2 . . ?
C25 C23 H23 110.7 . . ?
C26 C25 H25 128.0 . . ?
C23 C25 H25 111.8 . . ?
C3 C2 H2A 112.5 . . ?
C1 C2 H2A 109.8 . . ?
C3 C2 H2B 101.4 . . ?
C1 C2 H2B 119.1 . . ?
H2A C2 H2B 104.0 . . ?
C21 C20 H20A 109.8 . . ?
C19 C20 H20A 111.6 . . ?
C21 C20 H20B 105.0 . . ?
C19 C20 H20B 100.7 . . ?
H20A C20 H20B 117.9 . . ?
C8 C5 H5 123.1 . . ?
C3 C5 H5 115.9 . . ?
C17 C15 H15 121.3 . . ?
C13 C15 H15 118.6 . . ?
C15 C13 H13 122.3 . . ?
C12 C13 H13 115.6 . . ?
C21 C22 H22 111.1 . . ?
C24 C22 H22 125.3 . . ?
O5 C27 H27A 110.1 . . ?
O5 C27 H27B 109.3 . . ?
H27A C27 H27B 109.5 . . ?
O5 C27 H27C 109.0 . . ?
H27A C27 H27C 109.4 . . ?
H27B C27 H27C 109.5 . . ?
C6 C4 H4 131.4 . . ?
C3 C4 H4 104.7 . . ?
C7 C8 H8 120.5 . . ?
C5 C8 H8 119.4 . . ?
C26 C24 H24 120.2 . . ?
C22 C24 H24 118.4 . . ?
C7 C6 H6 120.6 . . ?
C4 C6 H6 119.3 . . ?
O2 C18 H18A 109.9 . . ?
O2 C18 H18B 110.0 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 108.7 . . ?
H18A C18 H18C 109.4 . . ?
H18B C18 H18C 109.4 . . ?
O1 C9 H9A 116.7 . . ?
O1 C9 H9B 105.3 . . ?
H9A C9 H9B 109.5 . . ?
O1 C9 H9C 106.1 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O6 C28 H28A 94.1 . . ?
O6 C28 H28B 112.7 . . ?
H28A C28 H28B 109.4 . . ?
O6 C28 H28C 120.4 . . ?
H28A C28 H28C 109.4 . . ?
H28B C28 H28C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N3 1.852(3) . ?
Ni1 N3 1.852(3) 3_765 ?
Ni1 N1 1.861(2) . ?
Ni1 N1 1.861(2) 3_765 ?
N1 C1 1.291(4) . ?
O3 C19 1.253(4) . ?
N2 C1 1.357(4) . ?
N2 C10 1.374(4) . ?
C10 N3 1.282(3) . ?
C10 C11 1.518(4) . ?
O4 C19 1.251(3) . ?
C19 C20 1.524(4) . ?
C1 C2 1.511(4) . ?
C14 C16 1.379(5) . ?
C14 C12 1.393(5) . ?
C12 C13 1.387(5) . ?
C12 C11 1.519(4) . ?
O2 C17 1.365(4) . ?
O2 C18 1.411(6) . ?
C3 C4 1.386(5) . ?
C3 C5 1.399(5) . ?
C3 C2 1.505(5) . ?
C21 C22 1.374(5) . ?
C21 C23 1.379(5) . ?
C21 C20 1.509(5) . ?
C16 C17 1.393(5) . ?
C17 C15 1.379(6) . ?
C23 C25 1.398(5) . ?
C25 C26 1.375(5) . ?
C26 O5 1.363(5) . ?
C26 C24 1.373(5) . ?
C5 C8 1.382(7) . ?
O5 C27 1.416(5) . ?
C15 C13 1.380(5) . ?
C22 C24 1.380(6) . ?
C4 C6 1.385(7) . ?
C8 C7 1.358(7) . ?
C6 C7 1.377(7) . ?
C7 O1 1.379(7) . ?
O1 C9 1.216(13) . ?
O6 C28 1.403(5) . ?
N1 H1 1.0773 . ?
N2 H2 1.0228 . ?
N3 H3 0.9650 . ?
C14 H14 0.9625 . ?
C11 H11A 1.1144 . ?
C11 H11B 1.2402 . ?
C16 H16 0.9594 . ?
C23 H23 0.9854 . ?
C25 H25 0.9476 . ?
C2 H2A 1.0288 . ?
C2 H2B 0.9843 . ?
C20 H20A 0.9298 . ?
C20 H20B 1.1143 . ?
C5 H5 1.0698 . ?
C15 H15 0.8867 . ?
C13 H13 0.9305 . ?
C22 H22 0.8724 . ?
C27 H27A 0.9597 . ?
C27 H27B 0.9595 . ?
C27 H27C 0.9603 . ?
C4 H4 1.0237 . ?
C8 H8 0.9614 . ?
C24 H24 0.9269 . ?
C6 H6 0.9588 . ?
C18 H18A 0.9599 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9608 . ?
C9 H9A 0.9604 . ?
C9 H9B 0.9599 . ?
C9 H9C 0.9592 . ?
C28 H28A 0.9606 . ?
C28 H28B 0.9601 . ?
C28 H28C 0.9603 . ?
