#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:31:18 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179332 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/29/4322959.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_4322959
loop_
_publ_author_name
'Vladimir N. Ikorskii'
'Victor I. Ovcharenko'
'Yurii G. Shvedenkov'
'Galina V. Romanenko'
'Sergei V. Fokin'
'Renad Z. Sagdeev'
_publ_section_title
;
 Molecular Magnets Based on Nickel(II) Complexes with 3-Imidazoline
 Nitroxides and Alcohols
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4360
_journal_page_last               4367
_journal_paper_doi               10.1021/ic9801847
_journal_volume                  37
_journal_year                    1998
_chemical_formula_sum            'C25 H38 F6 N4 Ni O6'
_chemical_formula_weight         663.30
_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                 110.61(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.028(4)
_cell_length_b                   10.943(2)
_cell_length_c                   14.405(3)
_cell_measurement_temperature    293(2)
_cell_volume                     3102.6(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.432
_diffrn_measured_fraction_theta_max 0.432
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3148
_diffrn_reflns_theta_full        26.96
_diffrn_reflns_theta_max         26.96
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.704
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0131(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3071
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0571P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0810
_reflns_number_gt                2549
_reflns_number_total             3071
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic9801847_3.cif
_cod_data_source_block           NiL2(HO(CH2)5OH)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to the
built-in table from CIF Core dictionary named 'cif_core.dic' version
2.4.1 from 2010-06-29 (4 times).

'_geom_angle_publ_flag' value 'Y'
changed to 'y' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (11
times).

Automatic conversion script
Id: cif_fix_values 1673 2011-04-08 12:14:43Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0571P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0571P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        3102.6(10)
_cod_database_code               4322959
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni 0.2500 0.2500 0.5000 0.03232(12) Uani 1 d S . .
O1 O 0.29049(7) 0.08675(11) 0.49461(10) 0.0454(3) Uani 1 d . . .
C1 C 0.33716(9) 0.06017(16) 0.46164(13) 0.0402(4) Uani 1 d . . .
C11 C 0.35858(13) -0.0729(2) 0.47862(17) 0.0601(6) Uani 1 d . . .
F1 F 0.40542(11) -0.10707(14) 0.44333(15) 0.1113(7) Uani 1 d . . .
F2 F 0.38243(12) -0.10018(16) 0.57231(13) 0.1306(9) Uani 1 d . . .
F3 F 0.30796(11) -0.14668(14) 0.4371(2) 0.1492(11) Uani 1 d . . .
C2 C 0.36939(10) 0.13322(18) 0.41666(14) 0.0452(4) Uani 1 d . . .
H2 H 0.4010(11) 0.102(2) 0.3975(16) 0.056(6) Uiso 1 d . . .
C3 C 0.35584(9) 0.26008(16) 0.39870(12) 0.0397(4) Uani 1 d . . .
C4 C 0.39578(10) 0.33149(19) 0.34741(16) 0.0511(5) Uani 1 d . . .
C41 C 0.47137(13) 0.3388(3) 0.4078(3) 0.0756(8) Uani 1 d . . .
H411 H 0.4930(15) 0.401(3) 0.374(2) 0.096(9) Uiso 1 d . . .
H412 H 0.4768(14) 0.360(3) 0.467(2) 0.084(10) Uiso 1 d . . .
H413 H 0.4895(16) 0.259(3) 0.412(2) 0.090(10) Uiso 1 d . . .
C42 C 0.3839(2) 0.2851(4) 0.2427(2) 0.0869(9) Uani 1 d . . .
H421 H 0.3373(19) 0.283(3) 0.206(3) 0.115(13) Uiso 1 d . . .
H422 H 0.4032(16) 0.348(3) 0.216(2) 0.104(10) Uiso 1 d . . .
H422 H 0.4037(15) 0.203(3) 0.247(2) 0.097(10) Uiso 1 d . . .
N11 N 0.36420(9) 0.44990(16) 0.34399(15) 0.0619(5) Uani 1 d . . .
O11 O 0.37844(10) 0.54301(17) 0.30178(16) 0.0906(6) Uani 1 d . . .
C5 C 0.31459(10) 0.45383(17) 0.39546(16) 0.0486(5) Uani 1 d . . .
C51 C 0.24711(13) 0.4982(3) 0.3223(2) 0.0684(7) Uani 1 d . . .
H511 H 0.2182(12) 0.510(2) 0.3562(17) 0.063(7) Uiso 1 d . . .
H512 H 0.2289(15) 0.434(3) 0.267(2) 0.101(11) Uiso 1 d . . .
H513 H 0.2560(13) 0.575(3) 0.304(2) 0.084(8) Uiso 1 d . . .
C52 C 0.34124(15) 0.5352(2) 0.4868(2) 0.0658(7) Uani 1 d . . .
H521 H 0.3111(14) 0.533(3) 0.522(2) 0.084(9) Uiso 1 d . . .
H522 H 0.3511(11) 0.612(2) 0.4715(16) 0.060(6) Uiso 1 d . . .
H523 H 0.3834(14) 0.503(3) 0.536(2) 0.083(8) Uiso 1 d . . .
N1 N 0.31229(7) 0.32416(12) 0.42344(10) 0.0369(3) Uani 1 d . . .
O01 O 0.17231(7) 0.20995(16) 0.36161(11) 0.0515(4) Uani 1 d . . .
H01 H 0.1736(14) 0.160(3) 0.333(2) 0.075(10) Uiso 1 d . . .
C011 C 0.0991(2) 0.2263(4) 0.3402(3) 0.0435(9) Uani 0.50 d P . .
H111 H 0.094(2) 0.256(4) 0.398(4) 0.045(12) Uiso 0.50 d P . .
H112 H 0.078(2) 0.152(4) 0.323(3) 0.049(11) Uiso 0.50 d P . .
C021 C 0.0711(2) 0.3196(5) 0.2601(4) 0.0620(12) Uani 0.50 d P . .
H211 H 0.071(3) 0.267(5) 0.204(5) 0.079(18) Uiso 0.50 d P . .
H212 H 0.108(2) 0.398(4) 0.247(4) 0.067(13) Uiso 0.50 d P . .
C03 C 0.0000 0.3547(4) 0.2500 0.0752(13) Uani 1 d S . .
H31 H -0.004(3) 0.413(4) 0.218(4) 0.072(19) Uiso 0.50 d P . .
H32 H 0.005(4) 0.373(7) 0.341(6) 0.13(3) Uiso 0.50 d P . .
C022 C -0.0525(2) 0.2565(5) 0.1985(4) 0.0549(10) Uani 0.50 d P . .
H221 H -0.029(2) 0.175(5) 0.223(4) 0.067(14) Uiso 0.50 d P . .
H222 H -0.060(4) 0.231(5) 0.128(5) 0.083(19) Uiso 0.50 d P . .
C012 C -0.1209(2) 0.2929(5) 0.1977(4) 0.0568(11) Uani 0.50 d P . .
H121 H -0.124(2) 0.378(5) 0.175(4) 0.069(14) Uiso 0.50 d P . .
H122 H -0.116(3) 0.293(5) 0.266(5) 0.065(14) Uiso 0.50 d P . .
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'
F F 0.0171 0.0103 '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
O1 Ni O1 180.0 . 7_556 ?
O1 Ni O01 88.66(6) . . y
O1 Ni O01 91.34(6) 7_556 . ?
O1 Ni O01 91.34(6) . 7_556 ?
O1 Ni O01 88.66(6) 7_556 7_556 ?
O01 Ni O01 180.0 . 7_556 ?
O1 Ni N1 91.58(5) . 7_556 ?
O1 Ni N1 88.42(5) 7_556 7_556 ?
O01 Ni N1 89.85(6) . 7_556 ?
O01 Ni N1 90.15(6) 7_556 7_556 ?
O1 Ni N1 88.42(5) . . y
O1 Ni N1 91.58(5) 7_556 . ?
O01 Ni N1 90.15(6) . . y
O01 Ni N1 89.85(6) 7_556 . ?
N1 Ni N1 180.0 7_556 . ?
C1 O1 Ni 128.27(11) . . ?
O1 C1 C2 129.04(17) . . ?
O1 C1 C11 112.66(16) . . ?
C2 C1 C11 118.29(17) . . ?
F2 C11 F3 106.8(2) . . ?
F2 C11 F1 105.6(2) . . ?
F3 C11 F1 104.4(2) . . ?
F2 C11 C1 111.85(18) . . ?
F3 C11 C1 111.9(2) . . ?
F1 C11 C1 115.57(19) . . ?
C1 C2 C3 124.21(17) . . ?
C1 C2 H2 119.4(14) . . ?
C3 C2 H2 116.4(14) . . ?
N1 C3 C2 126.33(17) . . ?
N1 C3 C4 114.86(16) . . ?
C2 C3 C4 118.80(16) . . ?
N11 C4 C3 98.72(15) . . ?
N11 C4 C41 110.3(2) . . ?
C3 C4 C41 113.2(2) . . ?
N11 C4 C42 110.5(2) . . ?
C3 C4 C42 112.6(2) . . ?
C41 C4 C42 110.9(3) . . ?
C4 C41 H411 108.0(16) . . ?
C4 C41 H412 109.4(19) . . ?
H411 C41 H412 111(2) . . ?
C4 C41 H413 107.8(19) . . ?
H411 C41 H413 114(2) . . ?
H412 C41 H413 106(3) . . ?
C4 C42 H421 110(2) . . ?
C4 C42 H422 102.2(19) . . ?
H421 C42 H422 108(3) . . ?
C4 C42 H422 108.6(18) . . ?
H421 C42 H422 111(3) . . ?
H422 C42 H422 118(3) . . ?
O11 N11 C4 123.31(17) . . y
O11 N11 C5 122.79(18) . . y
C4 N11 C5 113.89(15) . . y
N11 C5 N1 101.83(15) . . ?
N11 C5 C51 108.27(19) . . ?
N1 C5 C51 112.52(18) . . ?
N11 C5 C52 109.89(18) . . ?
N1 C5 C52 111.28(18) . . ?
C51 C5 C52 112.5(2) . . ?
C5 C51 H511 108.0(15) . . ?
C5 C51 H512 108.7(16) . . ?
H511 C51 H512 112(2) . . ?
C5 C51 H513 104.9(17) . . ?
H511 C51 H513 106(2) . . ?
H512 C51 H513 117(2) . . ?
C5 C52 H521 109.7(17) . . ?
C5 C52 H522 112.1(14) . . ?
H521 C52 H522 114(2) . . ?
C5 C52 H523 111.8(16) . . ?
H521 C52 H523 102(2) . . ?
H522 C52 H523 106(2) . . ?
C3 N1 C5 110.43(15) . . ?
C3 N1 Ni 123.61(11) . . ?
C5 N1 Ni 125.91(11) . . ?
C012 O01 C011 44.5(3) 2 . ?
C012 O01 Ni 126.4(2) 2 . y
C011 O01 Ni 124.90(19) . . y
C012 O01 H01 109(2) 2 . y
C011 O01 H01 103(2) . . y
Ni O01 H01 123(2) . . y
C022 C011 C012 90.1(5) 2 2 ?
C022 C011 O01 155.1(5) 2 . ?
C012 C011 O01 66.3(3) 2 . ?
C022 C011 C021 45.7(4) 2 . ?
C012 C011 C021 44.5(3) 2 . ?
O01 C011 C021 110.1(4) . . ?
C022 C011 H111 89(3) 2 . ?
C012 C011 H111 114(3) 2 . ?
O01 C011 H111 107(3) . . ?
C021 C011 H111 108(3) . . ?
C022 C011 H112 82(3) 2 . ?
C012 C011 H112 134(3) 2 . ?
O01 C011 H112 109(3) . . ?
C021 C011 H112 112(3) . . ?
H111 C011 H112 111(4) . . ?
C012 C021 C022 89.1(6) 2 2 ?
C012 C021 C011 47.4(4) 2 . ?
C022 C021 C011 41.8(3) 2 . ?
C012 C021 C03 152.1(7) 2 . ?
C022 C021 C03 70.8(4) 2 . ?
C011 C021 C03 110.9(4) . . ?
C012 C021 H211 92(4) 2 . ?
C022 C021 H211 101(3) 2 . ?
C011 C021 H211 97(3) . . ?
C03 C021 H211 110(4) . . ?
C012 C021 H212 74(2) 2 . ?
C022 C021 H212 157(2) 2 . ?
C011 C021 H212 120(2) . . ?
C03 C021 H212 118(2) . . ?
H211 C021 H212 96(4) . . ?
C021 C03 C021 150.4(5) 2 . ?
C021 C03 C022 41.4(3) 2 . ?
C021 C03 C022 113.1(4) . . ?
C021 C03 C022 113.1(4) 2 2 ?
C021 C03 C022 41.4(3) . 2 ?
C022 C03 C022 90.9(4) . 2 ?
C021 C03 H31 105(5) 2 . ?
C021 C03 H31 99(5) . . ?
C022 C03 H31 113(4) . . ?
C022 C03 H31 140(5) 2 . ?
C021 C03 H32 82(3) 2 . ?
C021 C03 H32 102(3) . . ?
C022 C03 H32 113(3) . . ?
C022 C03 H32 80(3) 2 . ?
H31 C03 H32 115(6) . . ?
C011 C022 C021 92.5(5) 2 2 ?
C011 C022 C012 47.7(4) 2 . ?
C021 C022 C012 44.8(4) 2 . ?
C011 C022 C03 154.3(6) 2 . ?
C021 C022 C03 67.8(4) 2 . ?
C012 C022 C03 110.3(4) . . ?
C011 C022 H221 99(3) 2 . ?
C021 C022 H221 126(3) 2 . ?
C012 C022 H221 125(3) . . ?
C03 C022 H221 106(3) . . ?
C011 C022 H222 64(4) 2 . ?
C021 C022 H222 141(4) 2 . ?
C012 C022 H222 105(4) . . ?
C03 C022 H222 121(4) . . ?
H221 C022 H222 90(4) . . ?
C021 C012 C011 88.1(5) 2 2 ?
C021 C012 O01 155.0(6) 2 2 ?
C011 C012 O01 69.2(3) 2 2 ?
C021 C012 C022 46.1(4) 2 . ?
C011 C012 C022 42.1(3) 2 . ?
O01 C012 C022 111.0(4) 2 . ?
C021 C012 H121 82(3) 2 . ?
C011 C012 H121 117(3) 2 . ?
O01 C012 H121 117(3) 2 . ?
C022 C012 H121 102(3) . . ?
C021 C012 H122 72(3) 2 . ?
C011 C012 H122 127(3) 2 . ?
O01 C012 H122 113(3) 2 . ?
C022 C012 H122 104(3) . . ?
H121 C012 H122 108(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
Ni O1 1.9922(12) . y
Ni O1 1.9922(12) 7_556 ?
Ni O01 2.1313(17) . y
Ni O01 2.1313(17) 7_556 ?
Ni N1 2.1465(14) 7_556 ?
Ni N1 2.1465(14) . y
O1 C1 1.265(2) . ?
C1 C2 1.352(3) . ?
C1 C11 1.518(3) . ?
C11 F2 1.298(3) . ?
C11 F3 1.302(3) . ?
C11 F1 1.312(3) . ?
C2 C3 1.422(3) . ?
C2 H2 0.87(2) . ?
C3 N1 1.299(2) . ?
C3 C4 1.516(3) . ?
C4 N11 1.449(3) . ?
C4 C41 1.522(3) . ?
C4 C42 1.527(4) . ?
C41 H411 1.03(3) . ?
C41 H412 0.85(3) . ?
C41 H413 0.94(3) . ?
C42 H421 0.93(4) . ?
C42 H422 0.95(3) . ?
C42 H422 0.98(3) . ?
N11 O11 1.275(2) . y
N11 C5 1.478(3) . ?
C5 N1 1.481(2) . ?
C5 C51 1.519(3) . ?
C5 C52 1.523(3) . ?
C51 H511 0.91(2) . ?
C51 H512 1.04(3) . ?
C51 H513 0.92(3) . ?
C52 H521 0.94(3) . ?
C52 H522 0.91(2) . ?
C52 H523 0.98(3) . ?
O01 C012 1.439(5) 2 ?
O01 C011 1.470(4) . ?
O01 H01 0.69(3) . ?
C011 C022 0.999(6) 2 ?
C011 C012 1.102(6) 2 ?
C011 C021 1.497(7) . ?
C011 H111 0.93(5) . ?
C011 H112 0.92(5) . ?
C021 C012 1.050(6) 2 ?
C021 C022 1.072(6) 2 ?
C021 C03 1.501(5) . ?
C021 H211 0.99(6) . ?
C021 H212 1.21(5) . ?
C03 C021 1.501(5) 2 ?
C03 C022 1.531(6) . ?
C03 C022 1.531(6) 2 ?
C03 H31 0.78(5) . ?
C03 H32 1.30(7) . ?
C022 C011 0.999(6) 2 ?
C022 C021 1.072(6) 2 ?
C022 C012 1.489(7) . ?
C022 H221 1.02(5) . ?
C022 H222 1.02(7) . ?
C012 C021 1.050(6) 2 ?
C012 C011 1.102(6) 2 ?
C012 O01 1.439(5) 2 ?
C012 H121 0.98(5) . ?
C012 H122 0.95(6) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O01 H01 O11 0.69(3) 2.26(3) 2.872(2) 149(3) 4_545
