#------------------------------------------------------------------------------
#$Date: 2016-03-23 01:24:16 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179139 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/00/4310046.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_4310046
loop_
_publ_author_name
'Nicolas Bréfuel'
'Christine Lepetit'
'Sergiu Shova'
'Françoise Dahan'
'Jean-Pierre Tuchagues'
_publ_section_title
;
Complexation to FeII, NiII, and ZnII of Multidentate Ligands Resulting from
Condensation of 2-Pyridinecarboxaldehyde with α,ω-Triamines: Selective
Imidazolidine/Hexahydropyrimidine Ring Opening Revisited
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              8916
_journal_page_last               8928
_journal_paper_doi               10.1021/ic050791b
_journal_volume                  44
_journal_year                    2005
_chemical_formula_moiety         'C19 H21 N7 Ni S2'
_chemical_formula_sum            'C19 H21 N7 Ni S2'
_chemical_formula_weight         470.26
_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_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                 92.834(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1512(16)
_cell_length_b                   13.2683(16)
_cell_length_c                   14.217(2)
_cell_measurement_reflns_used    3690
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      31.90
_cell_measurement_theta_min      2.80
_cell_volume                     2100.9(5)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  omega-Phi
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.70930
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_av_sigmaI/netI    0.1076
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14910
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.25
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.143
_exptl_absorpt_correction_T_max  0.9141
_exptl_absorpt_correction_T_min  0.6706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'R. H. Blessing, Acta Cryst., 1995, a51, 33'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.746
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.858
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4146
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.858
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0488P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                2164
_reflns_number_total             4146
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic050791bsi20050517_050021.cif
_cod_data_source_block           NiLB(NCS)2
_cod_original_cell_volume        2101.0(5)
_cod_database_code               4310046
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 0.24755(5) 0.12880(4) 0.74216(4) 0.03465(18) Uani 1 1 d . . .
S1 S 0.32184(13) -0.03016(10) 1.04218(8) 0.0561(4) Uani 1 1 d . . .
S2 S 0.27158(13) 0.44054(10) 0.90165(10) 0.0610(4) Uani 1 1 d . . .
N1 N 0.4190(4) 0.1801(3) 0.7145(3) 0.0412(10) Uani 1 1 d . . .
N2 N 0.2153(4) 0.2113(3) 0.6229(2) 0.0395(10) Uani 1 1 d . . .
N3 N 0.0638(4) 0.0818(3) 0.7087(4) 0.0719(14) Uani 1 1 d . . .
N4 N 0.0695(4) -0.0744(3) 0.8033(3) 0.0568(12) Uani 1 1 d . . .
HN4 H 0.1510 -0.0650 0.8272 0.11(2) Uiso 1 1 d R . .
N5 N 0.2688(3) -0.0080(3) 0.6686(2) 0.0358(9) Uani 1 1 d . . .
N6 N 0.2992(3) 0.0567(3) 0.8647(3) 0.0431(10) Uani 1 1 d . . .
N7 N 0.2106(3) 0.2571(3) 0.8184(3) 0.0455(10) Uani 1 1 d . . .
C1 C 0.5217(5) 0.1605(4) 0.7611(4) 0.0559(14) Uani 1 1 d . . .
H1 H 0.5215 0.1177 0.8129 0.067 Uiso 1 1 calc R . .
C2 C 0.6312(5) 0.2018(4) 0.7354(4) 0.0642(16) Uani 1 1 d . . .
H2 H 0.7030 0.1839 0.7670 0.077 Uiso 1 1 calc R . .
C3 C 0.6292(6) 0.2685(4) 0.6633(4) 0.0647(16) Uani 1 1 d . . .
H3 H 0.6999 0.3000 0.6473 0.078 Uiso 1 1 calc R . .
C4 C 0.5247(6) 0.2898(4) 0.6142(4) 0.0606(16) Uani 1 1 d . . .
H4 H 0.5236 0.3347 0.5639 0.073 Uiso 1 1 calc R . .
C5 C 0.4201(5) 0.2438(3) 0.6398(3) 0.0430(12) Uani 1 1 d . . .
C6 C 0.3041(5) 0.2573(3) 0.5906(3) 0.0479(13) Uani 1 1 d . . .
H6 H 0.2952 0.2981 0.5375 0.057 Uiso 1 1 calc R . .
C7 C 0.0939(5) 0.2172(3) 0.5844(3) 0.0498(13) Uani 1 1 d . . .
H7A H 0.0934 0.2318 0.5175 0.060 Uiso 1 1 calc R . .
H7B H 0.0511 0.2706 0.6151 0.060 Uiso 1 1 calc R . .
C8 C 0.0346(5) 0.1173(4) 0.6005(3) 0.0612(15) Uani 1 1 d . . .
H8A H 0.0643 0.0674 0.5575 0.073 Uiso 1 1 calc R . .
H8B H -0.0515 0.1234 0.5886 0.073 Uiso 1 1 calc R . .
C9 C -0.0327(5) 0.1246(4) 0.7517(5) 0.091(2) Uani 1 1 d . . .
H10A H -0.1085 0.1021 0.7225 0.109 Uiso 1 1 calc R . .
H10B H -0.0293 0.1976 0.7497 0.109 Uiso 1 1 calc R . .
C10 C -0.0146(6) 0.0834(4) 0.8579(4) 0.0741(19) Uani 1 1 d . . .
H21A H 0.0633 0.1046 0.8842 0.089 Uiso 1 1 calc R . .
H21B H -0.0755 0.1123 0.8961 0.089 Uiso 1 1 calc R . .
C11 C -0.0228(6) -0.0289(4) 0.8609(4) 0.078(2) Uani 1 1 d . . .
H11A H -0.0115 -0.0519 0.9255 0.094 Uiso 1 1 calc R . .
H11B H -0.1018 -0.0501 0.8371 0.094 Uiso 1 1 calc R . .
C12 C 0.0619(5) -0.0321(3) 0.7097(4) 0.0508(13) Uani 1 1 d . . .
C13 C 0.1713(4) -0.0661(3) 0.6602(3) 0.0359(11) Uani 1 1 d . . .
C14 C 0.1694(5) -0.1555(3) 0.6093(3) 0.0503(13) Uani 1 1 d . . .
H14 H 0.1001 -0.1946 0.6046 0.060 Uiso 1 1 calc R . .
C15 C 0.2698(6) -0.1852(4) 0.5664(3) 0.0589(15) Uani 1 1 d . . .
H15 H 0.2694 -0.2444 0.5313 0.071 Uiso 1 1 calc R . .
C16 C 0.3713(5) -0.1276(4) 0.5751(3) 0.0543(14) Uani 1 1 d . . .
H16 H 0.4411 -0.1474 0.5471 0.065 Uiso 1 1 calc R . .
C17 C 0.3679(5) -0.0394(3) 0.6265(3) 0.0438(12) Uani 1 1 d . . .
H17 H 0.4368 0.0000 0.6324 0.053 Uiso 1 1 calc R . .
C19 C 0.3105(4) 0.0199(3) 0.9387(3) 0.0362(11) Uani 1 1 d . . .
C20 C 0.2365(4) 0.3332(4) 0.8519(3) 0.0368(11) Uani 1 1 d . . .
H12 H -0.031(4) -0.068(3) 0.688(3) 0.069(15) Uiso 1 1 d . . .
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'
S S 0.1246 0.1234 '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
_geom_angle_publ_flag
N2 Ni1 N6 172.72(16) . . ?
N2 Ni1 N7 87.85(14) . . ?
N6 Ni1 N7 89.64(14) . . ?
N2 Ni1 N1 78.07(16) . . ?
N6 Ni1 N1 95.21(15) . . ?
N7 Ni1 N1 92.21(14) . . ?
N2 Ni1 N5 93.95(13) . . ?
N6 Ni1 N5 89.20(13) . . ?
N7 Ni1 N5 174.29(15) . . ?
N1 Ni1 N5 93.47(14) . . ?
N2 Ni1 N3 81.14(18) . . ?
N6 Ni1 N3 105.99(17) . . ?
N7 Ni1 N3 98.07(16) . . ?
N1 Ni1 N3 156.41(18) . . ?
N5 Ni1 N3 76.89(15) . . ?
C1 N1 C5 118.3(4) . . ?
C1 N1 Ni1 128.5(3) . . ?
C5 N1 Ni1 113.2(3) . . ?
C6 N2 C7 125.0(4) . . ?
C6 N2 Ni1 116.8(4) . . ?
C7 N2 Ni1 118.1(3) . . ?
C9 N3 C12 113.2(4) . . ?
C9 N3 C8 100.1(4) . . ?
C12 N3 C8 107.2(4) . . ?
C9 N3 Ni1 122.1(4) . . ?
C12 N3 Ni1 107.4(3) . . ?
C8 N3 Ni1 105.5(3) . . ?
C12 N4 C11 109.9(4) . . ?
C12 N4 HN4 106.7 . . ?
C11 N4 HN4 115.0 . . ?
C13 N5 C17 117.6(4) . . ?
C13 N5 Ni1 115.5(3) . . ?
C17 N5 Ni1 126.8(3) . . ?
C19 N6 Ni1 169.1(4) . . ?
C20 N7 Ni1 152.7(4) . . ?
N1 C1 C2 122.4(5) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 118.1(6) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 120.5(5) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.1(5) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.5(5) . . ?
N1 C5 C6 114.3(4) . . ?
C4 C5 C6 124.2(5) . . ?
N2 C6 C5 117.4(4) . . ?
N2 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
N2 C7 C8 107.9(4) . . ?
N2 C7 H7A 110.1 . . ?
C8 C7 H7A 110.1 . . ?
N2 C7 H7B 110.1 . . ?
C8 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C7 C8 N3 109.3(4) . . ?
C7 C8 H8A 109.8 . . ?
N3 C8 H8A 109.8 . . ?
C7 C8 H8B 109.8 . . ?
N3 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
N3 C9 C10 102.2(5) . . ?
N3 C9 H10A 111.3 . . ?
C10 C9 H10A 111.3 . . ?
N3 C9 H10B 111.3 . . ?
C10 C9 H10B 111.3 . . ?
H10A C9 H10B 109.2 . . ?
C11 C10 C9 111.1(5) . . ?
C11 C10 H21A 109.4 . . ?
C9 C10 H21A 109.4 . . ?
C11 C10 H21B 109.4 . . ?
C9 C10 H21B 109.4 . . ?
H21A C10 H21B 108.0 . . ?
N4 C11 C10 110.3(4) . . ?
N4 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
N4 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
N4 C12 C13 107.5(4) . . ?
N4 C12 N3 113.4(4) . . ?
C13 C12 N3 106.5(4) . . ?
N4 C12 H12 95(2) . . ?
C13 C12 H12 119(2) . . ?
N3 C12 H12 115(2) . . ?
N5 C13 C14 122.2(4) . . ?
N5 C13 C12 117.4(4) . . ?
C14 C13 C12 120.5(4) . . ?
C15 C14 C13 119.3(5) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 119.6(5) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 118.6(5) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
N5 C17 C16 122.8(5) . . ?
N5 C17 H17 118.6 . . ?
C16 C17 H17 118.6 . . ?
N6 C19 S1 178.2(4) . . ?
N7 C20 S2 178.6(4) . . ?
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 N2 2.036(3) . ?
Ni1 N6 2.045(4) . ?
Ni1 N7 2.070(4) . ?
Ni1 N1 2.085(4) . ?
Ni1 N5 2.114(3) . ?
Ni1 N3 2.172(4) . ?
S1 C19 1.614(5) . ?
S2 C20 1.630(5) . ?
N1 C1 1.320(6) . ?
N1 C5 1.359(5) . ?
N2 C6 1.268(5) . ?
N2 C7 1.437(6) . ?
N3 C9 1.385(6) . ?
N3 C12 1.511(6) . ?
N3 C8 1.626(6) . ?
N4 C12 1.443(6) . ?
N4 C11 1.476(6) . ?
N4 HN4 0.9623 . ?
N5 C13 1.334(5) . ?
N5 C17 1.347(5) . ?
N6 C19 1.161(5) . ?
N7 C20 1.147(5) . ?
C1 C2 1.403(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.353(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.359(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.451(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.504(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.608(8) . ?
C9 H10A 0.9700 . ?
C9 H10B 0.9700 . ?
C10 C11 1.494(6) . ?
C10 H21A 0.9700 . ?
C10 H21B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.508(6) . ?
C12 H12 1.17(5) . ?
C13 C14 1.388(6) . ?
C14 C15 1.360(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.366(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
