#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/09/2210910.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_2210910
loop_
_publ_author_name
'Kopylovich, Maximilian N.'
'Luzyanin, Konstantin V.'
'Haukka, Matti'
'Pombeiro, Armando J. L.'
'Kukushkin, Vadim Yu.'
_publ_section_title
;Bis[1,1-bis(propan-2-iminooxy)-1H-isoindol-3-amine-κ³N,N',N'']nickel(II)
 dinitrate
;
_journal_coeditor_code           BV2035
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2846
_journal_page_last               m2848
_journal_paper_doi               10.1107/S1600536806040219
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Ni (C14 H18 N4 O2)2] (N O3)2'
_chemical_formula_moiety         'C28 H36 N8 Ni O4 2+ , 2N O3 -'
_chemical_formula_sum            'C28 H36 N10 Ni O10'
_chemical_formula_weight         731.38
_chemical_name_systematic
;
Bis[3,3-di-{N-(propan-2-imine)oxy}-3H-isoindol-1-amine-κ²N,N']nickel(II)
dinitrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.101(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.8430(16)
_cell_length_b                   9.4644(8)
_cell_length_c                   17.101(2)
_cell_measurement_reflns_used    10960
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.03
_cell_volume                     1745.0(4)
_computing_cell_refinement       'EvalCCD (Duisenberg et al.,  2003)'
_computing_data_collection       'COLLECT (Bruker Nonius, 2004)'
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'SHELXTL (Sheldrick 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2002 (Burla et al.,  2003)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10960
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.03
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_T_max  0.9290
_exptl_absorpt_correction_T_min  0.7341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.253
_refine_diff_density_min         -0.498
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0503
_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)+(0.0599P)²+3.615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1425
_reflns_number_gt                2498
_reflns_number_total             2968
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bv2035.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2210910
_cod_database_fobs_code          2210910
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Ni Ni1 1.0000 0.0000 0.5000 0.0232(2) Uani d S 1
O O1 0.9633(2) 0.1044(2) 0.33722(12) 0.0283(5) Uani d . 1
O O2 0.9495(2) 0.2818(2) 0.42912(13) 0.0274(5) Uani d . 1
O O3 0.5694(3) 0.1683(3) 0.30273(16) 0.0487(7) Uani d . 1
O O4 0.5813(3) 0.1929(3) 0.42913(17) 0.0475(7) Uani d . 1
O O5 0.6209(3) -0.0079(3) 0.37645(18) 0.0566(9) Uani d . 1
N N1 1.1198(3) 0.1244(3) 0.44381(15) 0.0262(6) Uani d . 1
N N2 0.9306(3) -0.0195(3) 0.37964(16) 0.0257(6) Uani d . 1
N N3 0.9066(3) 0.1996(3) 0.49150(15) 0.0264(6) Uani d . 1
N N4 1.3362(3) 0.1228(3) 0.47333(18) 0.0333(7) Uani d . 1
N N5 0.5916(3) 0.1203(3) 0.36911(18) 0.0341(7) Uani d . 1
C C1 1.0314(3) 0.1985(3) 0.38854(18) 0.0248(7) Uani d . 1
C C2 1.1069(3) 0.2959(3) 0.34261(18) 0.0261(7) Uani d . 1
C C3 1.0715(4) 0.3943(4) 0.28470(19) 0.0305(8) Uani d . 1
H H3 0.9870 0.4087 0.2655 0.037 Uiso calc R 1
C C4 1.1669(4) 0.4713(4) 0.2560(2) 0.0334(8) Uani d . 1
H H4 1.1464 0.5405 0.2165 0.040 Uiso calc R 1
C C5 1.2910(4) 0.4500(4) 0.2832(2) 0.0328(8) Uani d . 1
H H5 1.3532 0.5039 0.2617 0.039 Uiso calc R 1
C C6 1.3253(3) 0.3510(4) 0.34144(19) 0.0293(7) Uani d . 1
H H6 1.4098 0.3364 0.3607 0.035 Uiso calc R 1
C C7 1.2307(3) 0.2744(3) 0.37029(18) 0.0261(7) Uani d . 1
C C8 1.2325(3) 0.1670(3) 0.43367(18) 0.0265(7) Uani d . 1
C C9 0.8622(3) -0.1017(4) 0.33486(19) 0.0269(7) Uani d . 1
C C10 0.8166(3) -0.0649(4) 0.2522(2) 0.0340(8) Uani d . 1
H H10A 0.8467 0.0293 0.2398 0.051 Uiso calc PR 0.50
H H10B 0.7257 -0.0652 0.2459 0.051 Uiso calc PR 0.50
H H10C 0.8472 -0.1345 0.2165 0.051 Uiso calc PR 0.50
H H10D 0.7664 -0.1428 0.2283 0.051 Uiso calc PR 0.50
H H10E 0.8874 -0.0484 0.2222 0.051 Uiso calc PR 0.50
H H10F 0.7659 0.0209 0.2516 0.051 Uiso calc PR 0.50
C C11 0.8281(3) -0.2410(4) 0.3672(2) 0.0315(8) Uani d . 1
H H11A 0.8650 -0.2494 0.4219 0.047 Uiso calc R 1
H H11B 0.8593 -0.3172 0.3358 0.047 Uiso calc R 1
H H11C 0.7377 -0.2480 0.3651 0.047 Uiso calc R 1
C C12 0.8290(3) 0.2712(3) 0.52722(19) 0.0286(7) Uani d . 1
C C13 0.7792(4) 0.2061(4) 0.5964(2) 0.0366(9) Uani d . 1
H H13A 0.8130 0.1106 0.6045 0.055 Uiso calc R 1
H H13B 0.6885 0.2013 0.5871 0.055 Uiso calc R 1
H H13C 0.8032 0.2636 0.6432 0.055 Uiso calc R 1
C C14 0.7895(4) 0.4177(4) 0.5036(2) 0.0374(9) Uani d . 1
H H14A 0.8297 0.4461 0.4574 0.056 Uiso calc PR 0.50
H H14B 0.8137 0.4829 0.5471 0.056 Uiso calc PR 0.50
H H14C 0.6993 0.4203 0.4909 0.056 Uiso calc PR 0.50
H H14D 0.7321 0.4534 0.5395 0.056 Uiso calc PR 0.50
H H14E 0.7481 0.4166 0.4498 0.056 Uiso calc PR 0.50
H H14F 0.8625 0.4792 0.5060 0.056 Uiso calc PR 0.50
H H4B 1.334(4) 0.065(5) 0.514(2) 0.035(10) Uiso d . 1
H H4A 1.409(5) 0.168(6) 0.463(3) 0.064(15) Uiso d . 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N1 Ni1 N1 3_756 . 179.9990(10)
N1 Ni1 N2 3_756 3_756 76.95(10)
N1 Ni1 N2 . 3_756 103.05(10)
N1 Ni1 N2 3_756 . 103.05(10)
N1 Ni1 N2 . . 76.95(10)
N2 Ni1 N2 3_756 . 180.0
N1 Ni1 N3 3_756 3_756 77.40(10)
N1 Ni1 N3 . 3_756 102.60(10)
N2 Ni1 N3 3_756 3_756 83.94(10)
N2 Ni1 N3 . 3_756 96.06(10)
N1 Ni1 N3 3_756 . 102.60(10)
N1 Ni1 N3 . . 77.40(10)
N2 Ni1 N3 3_756 . 96.06(10)
N2 Ni1 N3 . . 83.94(10)
N3 Ni1 N3 3_756 . 179.9970(10)
C1 O1 N2 . . 110.0(2)
C1 O2 N3 . . 109.3(2)
C8 N1 C1 . . 108.9(3)
C8 N1 Ni1 . . 151.1(2)
C1 N1 Ni1 . . 100.03(19)
C9 N2 O1 . . 110.7(3)
C9 N2 Ni1 . . 139.5(2)
O1 N2 Ni1 . . 109.64(18)
C12 N3 O2 . . 110.4(3)
C12 N3 Ni1 . . 139.7(2)
O2 N3 Ni1 . . 109.86(17)
C8 N4 H4B . . 120(3)
C8 N4 H4A . . 117(3)
H4B N4 H4A . . 122(4)
O3 N5 O4 . . 122.2(3)
O3 N5 O5 . . 118.3(3)
O4 N5 O5 . . 119.5(3)
O1 C1 O2 . . 110.0(3)
O1 C1 N1 . . 111.5(3)
O2 C1 N1 . . 110.7(2)
O1 C1 C2 . . 109.9(2)
O2 C1 C2 . . 108.5(2)
N1 C1 C2 . . 106.1(3)
C3 C2 C7 . . 121.7(3)
C3 C2 C1 . . 131.3(3)
C7 C2 C1 . . 106.9(3)
C2 C3 C4 . . 116.3(3)
C2 C3 H3 . . 121.8
C4 C3 H3 . . 121.8
C5 C4 C3 . . 122.2(3)
C5 C4 H4 . . 118.9
C3 C4 H4 . . 118.9
C6 C5 C4 . . 120.9(3)
C6 C5 H5 . . 119.5
C4 C5 H5 . . 119.5
C5 C6 C7 . . 117.1(3)
C5 C6 H6 . . 121.5
C7 C6 H6 . . 121.5
C6 C7 C2 . . 121.7(3)
C6 C7 C8 . . 131.6(3)
C2 C7 C8 . . 106.6(3)
N1 C8 N4 . . 126.0(3)
N1 C8 C7 . . 111.5(3)
N4 C8 C7 . . 122.5(3)
N2 C9 C10 . . 122.8(3)
N2 C9 C11 . . 118.0(3)
C10 C9 C11 . . 119.3(3)
C9 C10 H10A . . 109.5
C9 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
C9 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
C9 C10 H10D . . 109.5
H10A C10 H10D . . 141.1
H10B C10 H10D . . 56.3
H10C C10 H10D . . 56.3
C9 C10 H10E . . 109.5
H10A C10 H10E . . 56.3
H10B C10 H10E . . 141.1
H10C C10 H10E . . 56.3
H10D C10 H10E . . 109.5
C9 C10 H10F . . 109.5
H10A C10 H10F . . 56.3
H10B C10 H10F . . 56.3
H10C C10 H10F . . 141.1
H10D C10 H10F . . 109.5
H10E C10 H10F . . 109.5
C9 C11 H11A . . 109.5
C9 C11 H11B . . 109.5
H11A C11 H11B . . 109.5
C9 C11 H11C . . 109.5
H11A C11 H11C . . 109.5
H11B C11 H11C . . 109.5
N3 C12 C13 . . 118.2(3)
N3 C12 C14 . . 123.0(3)
C13 C12 C14 . . 118.8(3)
C12 C13 H13A . . 109.5
C12 C13 H13B . . 109.5
H13A C13 H13B . . 109.5
C12 C13 H13C . . 109.5
H13A C13 H13C . . 109.5
H13B C13 H13C . . 109.5
C12 C14 H14A . . 109.5
C12 C14 H14B . . 109.5
H14A C14 H14B . . 109.5
C12 C14 H14C . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
C12 C14 H14D . . 109.5
H14A C14 H14D . . 141.1
H14B C14 H14D . . 56.3
H14C C14 H14D . . 56.3
C12 C14 H14E . . 109.5
H14A C14 H14E . . 56.3
H14B C14 H14E . . 141.1
H14C C14 H14E . . 56.3
H14D C14 H14E . . 109.5
C12 C14 H14F . . 109.5
H14A C14 H14F . . 56.3
H14B C14 H14F . . 56.3
H14C C14 H14F . . 141.1
H14D C14 H14F . . 109.5
H14E C14 H14F . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Ni1 N1 3_756 2.064(3)
Ni1 N1 . 2.064(3)
Ni1 N2 3_756 2.123(3)
Ni1 N2 . 2.123(3)
Ni1 N3 3_756 2.141(3)
Ni1 N3 . 2.141(3)
O1 C1 . 1.404(4)
O1 N2 . 1.443(3)
O2 C1 . 1.422(4)
O2 N3 . 1.437(3)
O3 N5 . 1.223(4)
O4 N5 . 1.250(4)
O5 N5 . 1.258(4)
N1 C8 . 1.316(4)
N1 C1 . 1.453(4)
N2 C9 . 1.273(4)
N3 C12 . 1.284(4)
N4 C8 . 1.318(5)
N4 H4B . 0.88(4)
N4 H4A . 0.93(6)
C1 C2 . 1.507(4)
C2 C3 . 1.384(5)
C2 C7 . 1.390(5)
C3 C4 . 1.396(5)
C3 H3 . 0.9500
C4 C5 . 1.391(6)
C4 H4 . 0.9500
C5 C6 . 1.389(5)
C5 H5 . 0.9500
C6 C7 . 1.389(5)
C6 H6 . 0.9500
C7 C8 . 1.485(4)
C9 C10 . 1.489(5)
C9 C11 . 1.491(5)
C10 H10A . 0.9800
C10 H10B . 0.9800
C10 H10C . 0.9800
C10 H10D . 0.9800
C10 H10E . 0.9800
C10 H10F . 0.9800
C11 H11A . 0.9800
C11 H11B . 0.9800
C11 H11C . 0.9800
C12 C13 . 1.485(5)
C12 C14 . 1.494(5)
C13 H13A . 0.9800
C13 H13B . 0.9800
C13 H13C . 0.9800
C14 H14A . 0.9800
C14 H14B . 0.9800
C14 H14C . 0.9800
C14 H14D . 0.9800
C14 H14E . 0.9800
C14 H14F . 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N4 H4B O5 3_756 0.88(4) 1.97(4) 2.783(4) 153(4)
N4 H4A O4 1_655 0.93(6) 2.03(6) 2.915(5) 159(5)
N4 H4B O4 3_756 0.88(4) 2.75(4) 3.492(5) 143(3)
N4 H4B N5 3_756 0.88(4) 2.72(4) 3.566(4) 161(3)
N4 H4A N5 1_655 0.93(6) 2.72(5) 3.449(4) 136(4)
