#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/57/2005794.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2005794
loop_
_publ_author_name
'Shan, B.-Z.'
'You, X.-Z.'
'Fun, H.-K.'
'Sivakumar, K.'
_publ_section_title
;
 [1,8-Bis(2-hydroxyethyl)-1,3,6,8,10,13-hexaazacyclotetradecane]nickel(II)
 Bis(maleonitriledithiolato)nickelate(II)
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              3035
_journal_page_last               3037
_journal_paper_doi               10.1107/S0108270196009389
_journal_volume                  52
_journal_year                    1996
_chemical_formula_iupac          '[Ni (C12 H30 N6 O2)] [Ni (C4 N2 S2)2]'
_chemical_formula_moiety         '[C12 H30 N6 Ni1 O2][C8 N4 Ni1 S4]'
_chemical_formula_sum            'C20 H30 N10 Ni2 O2 S4'
_chemical_formula_weight         688.20
_chemical_name_systematic
;
(1.8-bis(2-hydroxyethyl)-1,3,6,8,10,13-hexaazacyclotetradecane)
nickel(II)Bis(maleonitriledithiolate)nickelate(II)
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 93.64(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.181(2)
_cell_length_b                   9.911(1)
_cell_length_c                   19.114(4)
_cell_measurement_reflns_used    49
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      5
_cell_volume                     2870.1(8)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics
'SHELXTL/PC. Molecular graphics: PARST (Nardelli, 1983)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4 diffractometer'
_diffrn_measurement_method       'θ/2θ 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  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4076
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.14
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.641
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_correction_T_min  0.764
_exptl_absorpt_correction_type   'empirical, \y scans (XSCANS; Siemens, 1994)'
_exptl_crystal_colour            'Dark red'
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.44
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.059
_refine_ls_goodness_of_fit_obs   1.084
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_restrained_S_obs      1.084
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_obs          0.0330
_refine_ls_shift/esd_max         -0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0607P)²+0.8743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0993
_refine_ls_wR_factor_obs         0.0932
_reflns_number_observed          2793
_reflns_number_total             3284
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            mu1259.cif
_cod_data_source_block           asbz11
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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.

'_geom_bond_publ_flag' value 'Yes' changed to 'yes'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (21
time).

'_geom_angle_publ_flag' value 'Yes' changed to 'yes'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (8
times).

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

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0607P)^2^+0.8743P] 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^)+(0.0607P)^2^+0.8743P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               2005794
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_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
Ni1 1 0 0.5000 0.5000 0.0330(1) Uani d S Ni
Ni2 1 0.2500 0.7500 0.5000 0.0321(1) Uani d S Ni
S1 1 -0.05061(5) 0.37688(6) 0.58230(3) 0.0463(2) Uani d . S
S2 1 -0.03251(4) 0.68526(6) 0.55338(3) 0.0412(2) Uani d . S
O1 1 -0.03472(14) 1.0265(2) 0.59016(14) 0.0603(6) Uani d . O
N1 1 -0.1240(2) 0.4007(4) 0.76208(13) 0.0703(8) Uani d . N
N2 1 -0.1153(3) 0.8070(4) 0.7199(2) 0.0881(11) Uani d . N
N3 1 0.20973(13) 0.9272(2) 0.47100(10) 0.0360(4) Uani d . N
N4 1 0.14825(13) 0.9895(2) 0.57807(10) 0.0392(4) Uani d . N
N5 1 0.19005(14) 0.7568(2) 0.58535(10) 0.0370(4) Uani d . N
C1 1 -0.0737(2) 0.4946(3) 0.64587(12) 0.0393(5) Uani d . C
C2 1 -0.1018(2) 0.4429(3) 0.71123(13) 0.0484(6) Uani d . C
C3 1 -0.0674(2) 0.6276(3) 0.63334(12) 0.0395(5) Uani d . C
C4 1 -0.0935(2) 0.7272(3) 0.6827(2) 0.0543(7) Uani d . C
C5 1 0.1898(2) 0.8875(3) 0.62266(13) 0.0445(6) Uani d . C
C6 1 0.2252(2) 0.6479(3) 0.63307(14) 0.0519(7) Uani d . C
C7 1 0.2385(2) 0.5268(3) 0.5882(2) 0.0490(6) Uani d . C
C8 1 0.2052(2) 1.0334(3) 0.52451(14) 0.0433(5) Uani d . C
C9 1 0.1138(2) 1.1020(3) 0.61911(15) 0.0472(6) Uani d . C
C10 1 0.0261(2) 1.0637(3) 0.64625(15) 0.0496(6) Uani d . C
H1O 1 -0.0096(26) 0.9691(41) 0.5727(20) 0.076(13) Uiso d . H
H3N 1 0.1619(20) 0.9154(33) 0.4576(14) 0.046(8) Uiso d . H
H5N 1 0.1407(24) 0.7385(34) 0.5752(18) 0.063(10) Uiso d . H
H5A 1 0.1582(23) 0.8787(38) 0.6638(18) 0.075(11) Uiso d . H
H5B 1 0.2572(21) 0.9105(34) 0.6418(16) 0.058(8) Uiso d . H
H6A 1 0.1867(24) 0.6297(40) 0.6683(19) 0.081(11) Uiso d . H
H6B 1 0.2820(22) 0.6804(37) 0.6574(17) 0.062(9) Uiso d . H
H7A 1 0.2705(19) 0.4574(32) 0.6140(15) 0.048(8) Uiso d . H
H7B 1 0.1871(21) 0.4902(31) 0.5687(16) 0.048(8) Uiso d . H
H8A 1 0.2660(19) 1.0466(31) 0.5400(14) 0.043(7) Uiso d . H
H8B 1 0.1784(20) 1.1084(33) 0.4984(16) 0.056(9) Uiso d . H
H9A 1 0.1025(21) 1.1698(36) 0.5879(17) 0.060(9) Uiso d . H
H9B 1 0.1577(23) 1.1344(40) 0.6613(19) 0.078(11) Uiso d . H
H10A 1 0.0319(19) 0.9899(29) 0.6768(15) 0.049(8) Uiso d . H
H10B 1 0.0008(18) 1.1432(32) 0.6693(15) 0.048(8) Uiso d . H
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
S1 Ni1 S1 5_566 . 180.0 ?
S1 Ni1 S2 5_566 . 88.09(2) no
S1 Ni1 S2 . . 91.91(2) yes
S1 Ni1 S2 5_566 5_566 91.91(2) ?
S1 Ni1 S2 . 5_566 88.09(2) ?
S2 Ni1 S2 . 5_566 180.0 ?
N5 Ni2 N5 . 7_566 180.0 ?
N5 Ni2 N3 . . 93.07(8) yes
N5 Ni2 N3 7_566 . 86.93(8) no
N5 Ni2 N3 . 7_566 86.93(8) ?
N5 Ni2 N3 7_566 7_566 93.07(8) ?
N3 Ni2 N3 . 7_566 180.0 ?
C1 S1 Ni1 . . 103.08(9) yes
C3 S2 Ni1 . . 103.00(9) yes
C8 N3 C7 . 7_566 111.0(2) ?
C8 N3 Ni2 . . 118.6(2) yes
C7 N3 Ni2 7_566 . 108.92(15) yes
C5 N4 C8 . . 111.7(2) ?
C5 N4 C9 . . 111.8(2) ?
C8 N4 C9 . . 113.4(2) ?
C5 N5 C6 . . 110.5(2) ?
C5 N5 Ni2 . . 117.2(2) yes
C6 N5 Ni2 . . 108.92(15) yes
C3 C1 C2 . . 122.1(2) ?
C3 C1 S1 . . 120.9(2) ?
C2 C1 S1 . . 116.9(2) ?
N1 C2 C1 . . 179.0(4) ?
C1 C3 C4 . . 122.0(2) ?
C1 C3 S2 . . 120.4(2) ?
C4 C3 S2 . . 117.5(2) ?
N2 C4 C3 . . 178.0(4) ?
N4 C5 N5 . . 110.1(2) ?
N5 C6 C7 . . 106.6(2) ?
N3 C7 C6 7_566 . 106.7(2) ?
N4 C8 N3 . . 109.4(2) ?
N4 C9 C10 . . 110.1(2) ?
O1 C10 C9 . . 110.6(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 S1 5_566 2.1697(7) ?
Ni1 S1 . 2.1697(7) yes
Ni1 S2 . 2.1725(6) yes
Ni1 S2 5_566 2.1725(6) ?
Ni2 N5 . 1.919(2) yes
Ni2 N5 7_566 1.919(2) ?
Ni2 N3 . 1.929(2) yes
Ni2 N3 7_566 1.929(2) ?
S1 C1 . 1.736(2) yes
S2 C3 . 1.746(2) yes
O1 C10 . 1.419(4) yes
N1 C2 . 1.129(4) yes
N2 C4 . 1.128(4) yes
N3 C8 . 1.472(3) yes
N3 C7 7_566 1.490(3) yes
N4 C5 . 1.442(3) yes
N4 C8 . 1.448(3) yes
N4 C9 . 1.477(3) yes
N5 C5 . 1.479(3) yes
N5 C6 . 1.490(3) yes
C1 C3 . 1.344(4) yes
C1 C2 . 1.439(3) yes
C3 C4 . 1.438(4) yes
C6 C7 . 1.497(4) yes
C7 N3 7_566 1.490(3) ?
C9 C10 . 1.508(4) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
S1 Ni1 S1 C1 5_566 . -14.E1(10)
S2 Ni1 S1 C1 . . -7.10(9)
S2 Ni1 S1 C1 5_566 . 172.90(9)
S1 Ni1 S2 C3 5_566 . -173.64(8)
S1 Ni1 S2 C3 . . 6.36(8)
S2 Ni1 S2 C3 5_566 . 6.E1(8)
N5 Ni2 N3 C8 . . 38.4(2)
N5 Ni2 N3 C8 7_566 . -141.6(2)
N3 Ni2 N3 C8 7_566 . 12.E1(10)
N5 Ni2 N3 C7 . 7_566 166.7(2)
N5 Ni2 N3 C7 7_566 7_566 -13.3(2)
N3 Ni2 N3 C7 7_566 7_566 -12.E1(10)
N5 Ni2 N5 C5 7_566 . -13.E1(10)
N3 Ni2 N5 C5 . . -38.7(2)
N3 Ni2 N5 C5 7_566 . 141.3(2)
N5 Ni2 N5 C6 7_566 . 10.E1(10)
N3 Ni2 N5 C6 . . -165.0(2)
N3 Ni2 N5 C6 7_566 . 15.0(2)
Ni1 S1 C1 C3 . . 6.8(2)
Ni1 S1 C1 C2 . . -174.7(2)
C3 C1 C2 N1 . . 164.(17)
S1 C1 C2 N1 . . -14.(17)
C2 C1 C3 C4 . . -3.9(4)
S1 C1 C3 C4 . . 174.5(2)
C2 C1 C3 S2 . . 179.6(2)
S1 C1 C3 S2 . . -1.9(3)
Ni1 S2 C3 C1 . . -4.1(2)
Ni1 S2 C3 C4 . . 179.3(2)
C1 C3 C4 N2 . . -129.(10)
S2 C3 C4 N2 . . 48.(10)
C8 N4 C5 N5 . . -75.0(3)
C9 N4 C5 N5 . . 156.7(2)
C6 N5 C5 N4 . . -174.8(2)
Ni2 N5 C5 N4 . . 59.7(3)
C5 N5 C6 C7 . . -169.9(2)
Ni2 N5 C6 C7 . . -39.8(3)
N5 C6 C7 N3 . 7_566 50.6(3)
C5 N4 C8 N3 . . 73.3(3)
C9 N4 C8 N3 . . -159.3(2)
C7 N3 C8 N4 7_566 . 175.1(2)
Ni2 N3 C8 N4 . . -57.6(2)
C5 N4 C9 C10 . . -80.5(3)
C8 N4 C9 C10 . . 152.2(2)
N4 C9 C10 O1 . . -56.7(3)
