#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/23/2222353.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_2222353
loop_
_publ_author_name
'Temel, Ersin'
'Erer, Hakan'
'Yeşilel, Okan Zafer'
'Büyükgüngör, Orhan'
_publ_contact_author
;
'Orhan Büyükgüngör'
Department of Physics,
Faculty of Arts and Sciences,
Ondokuz Mayıs University,
Kurupelit
TR-55139
Samsun
Turkey
;
_publ_section_title
;
 Diaquabis(1,3-propanediamine)nickel(II) squarate tetrahydrate
;
_journal_coeditor_code           HK2703
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m735
_journal_page_last               m736
_journal_paper_doi               10.1107/S160053680902087X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Ni (C3 H10 N2 )2 (H2 O)2](C4 O4) , 4H2 O'
_chemical_formula_moiety         'C6 H24 N4 Ni O2, C4 O4, 4H2 O'
_chemical_formula_sum            'C10 H32 N4 Ni O10'
_chemical_formula_weight         427.09
_chemical_name_systematic
;
Diaquabis(1,3-propanediamine)nickel(II) squarate tetrahydrate
;
_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                 117.570(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.0429(4)
_cell_length_b                   9.1752(5)
_cell_length_c                   14.6510(8)
_cell_measurement_reflns_used    2204
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.02
_cell_measurement_theta_min      2.22
_cell_volume                     958.40(9)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS II diffractometer'
_diffrn_measurement_method       'w-scan rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7288
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.72
_exptl_absorpt_coefficient_mu    1.06
_exptl_absorpt_correction_T_max  0.9487
_exptl_absorpt_correction_T_min  0.6383
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             456.0
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0211
_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)+(0.0282P)²+0.2118P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0526
_refine_ls_wR_factor_ref         0.0539
_reflns_number_gt                2003
_reflns_number_total             2204
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2703.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222353
_cod_database_fobs_code          2222353
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni1 0.5000 0.5000 0.5000 0.02232(7) Uani d S 1 . .
O O1 0.64732(15) 0.39000(12) 0.43015(8) 0.0383(2) Uani d . 1 . .
H H1E 0.713(3) 0.432(2) 0.4113(14) 0.051(5) Uiso d . 1 . .
H H1F 0.692(3) 0.315(3) 0.4515(15) 0.063(6) Uiso d . 1 . .
O O2 0.73874(13) 1.09844(11) 0.49933(8) 0.0414(2) Uani d . 1 . .
O O3 0.86500(14) 0.77497(10) 0.46843(9) 0.0434(2) Uani d . 1 . .
O O4 0.34274(18) 0.07964(14) 0.36302(9) 0.0489(3) Uani d . 1 . .
H H4A 0.455(3) 0.082(2) 0.3910(16) 0.067(6) Uiso d . 1 . .
H H4B 0.317(3) 0.029(3) 0.401(2) 0.075(7) Uiso d . 1 . .
O O5 0.85562(18) 0.53525(13) 0.35580(11) 0.0462(3) Uani d . 1 . .
H H5A 0.871(3) 0.611(3) 0.3859(17) 0.066(6) Uiso d . 1 . .
H H5B 0.803(3) 0.550(3) 0.2975(19) 0.072(8) Uiso d . 1 . .
N N1 0.24635(14) 0.41813(12) 0.38210(8) 0.0317(2) Uani d . 1 . .
H H1A 0.2548 0.3203 0.3845 0.038 Uiso calc R 1 . .
H H1B 0.1547 0.4421 0.3983 0.038 Uiso calc R 1 . .
N N2 0.47942(14) 0.69084(11) 0.41632(8) 0.0294(2) Uani d . 1 . .
H H2A 0.4236 0.7588 0.4372 0.035 Uiso calc R 1 . .
H H2B 0.5970 0.7221 0.4355 0.035 Uiso calc R 1 . .
C C1 0.1833(2) 0.46195(17) 0.27461(10) 0.0423(3) Uani d . 1 . .
H H1C 0.0568 0.4263 0.2326 0.051 Uiso calc R 1 . .
H H1D 0.2640 0.4173 0.2497 0.051 Uiso calc R 1 . .
C C2 0.1860(2) 0.62587(16) 0.26262(11) 0.0438(3) Uani d . 1 . .
H H2C 0.1144 0.6502 0.1902 0.053 Uiso calc R 1 . .
H H2D 0.1242 0.6710 0.2987 0.053 Uiso calc R 1 . .
C C3 0.3806(2) 0.68931(16) 0.30294(10) 0.0406(3) Uani d . 1 . .
H H3A 0.4520 0.6320 0.2776 0.049 Uiso calc R 1 . .
H H3B 0.3718 0.7880 0.2774 0.049 Uiso calc R 1 . .
C C4 0.88219(16) 1.04411(13) 0.49952(9) 0.0269(2) Uani d . 1 . .
C C5 0.93844(16) 0.89777(13) 0.48539(9) 0.0271(2) Uani 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
_geom_angle_publ_flag
O1 Ni1 O1 . 3_666 180.00(5) ?
N1 Ni1 N1 3_666 . 180.0 ?
N1 Ni1 O1 3_666 . 91.14(4) ?
N1 Ni1 O1 . . 88.86(4) yes
N1 Ni1 O1 3_666 3_666 88.86(4) ?
N1 Ni1 O1 . 3_666 91.14(4) ?
N2 Ni1 O1 3_666 . 88.54(4) ?
N2 Ni1 O1 . . 91.46(4) yes
N2 Ni1 O1 3_666 3_666 91.46(4) ?
N2 Ni1 O1 . 3_666 88.54(4) ?
N2 Ni1 N2 3_666 . 180.0 ?
N2 Ni1 N1 3_666 3_666 91.94(4) ?
N2 Ni1 N1 . 3_666 88.06(4) ?
N2 Ni1 N1 3_666 . 88.06(4) ?
N2 Ni1 N1 . . 91.94(4) yes
Ni1 O1 H1E . . 122.4(14) ?
Ni1 O1 H1F . . 118.8(15) ?
H1E O1 H1F . . 108.4(19) ?
H4A O4 H4B . . 104(2) ?
H5A O5 H5B . . 109(2) ?
Ni1 N1 H1A . . 107.3 ?
Ni1 N1 H1B . . 107.3 ?
C1 N1 Ni1 . . 120.23(9) ?
C1 N1 H1A . . 107.3 ?
C1 N1 H1B . . 107.3 ?
H1A N1 H1B . . 106.9 ?
Ni1 N2 H2A . . 107.2 ?
Ni1 N2 H2B . . 107.2 ?
C3 N2 Ni1 . . 120.41(8) ?
C3 N2 H2A . . 107.2 ?
C3 N2 H2B . . 107.2 ?
H2A N2 H2B . . 106.9 ?
N1 C1 C2 . . 112.30(11) ?
N1 C1 H1C . . 109.1 ?
C2 C1 H1C . . 109.1 ?
N1 C1 H1D . . 109.1 ?
C2 C1 H1D . . 109.1 ?
H1C C1 H1D . . 107.9 ?
C3 C2 C1 . . 113.88(12) ?
C3 C2 H2C . . 108.8 ?
C1 C2 H2C . . 108.8 ?
C3 C2 H2D . . 108.8 ?
C1 C2 H2D . . 108.8 ?
H2C C2 H2D . . 107.7 ?
N2 C3 C2 . . 111.42(11) ?
N2 C3 H3A . . 109.3 ?
C2 C3 H3A . . 109.3 ?
N2 C3 H3B . . 109.3 ?
C2 C3 H3B . . 109.3 ?
H3A C3 H3B . . 108.0 ?
O2 C4 C5 . 3_776 134.42(12) ?
O2 C4 C5 . . 135.11(12) ?
C5 C4 C5 3_776 . 90.46(9) ?
O3 C5 C4 . 3_776 135.11(12) ?
O3 C5 C4 . . 135.35(12) ?
C4 C5 C4 3_776 . 89.54(9) ?
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 O1 3_666 2.1429(9) ?
Ni1 N1 3_666 2.1090(10) ?
Ni1 N2 3_666 2.0997(10) ?
O1 Ni1 . 2.1429(9) yes
O1 H1E . 0.80(2) ?
O1 H1F . 0.77(2) ?
O4 H4A . 0.80(2) ?
O4 H4B . 0.82(3) ?
O5 H5A . 0.80(2) ?
O5 H5B . 0.77(2) ?
N1 Ni1 . 2.1090(10) yes
N1 H1A . 0.9000 ?
N1 H1B . 0.9000 ?
N2 Ni1 . 2.0997(10) yes
N2 H2A . 0.9000 ?
N2 H2B . 0.9000 ?
C1 N1 . 1.4695(17) ?
C1 C2 . 1.516(2) ?
C1 H1C . 0.9700 ?
C1 H1D . 0.9700 ?
C2 C3 . 1.511(2) ?
C2 H2C . 0.9700 ?
C2 H2D . 0.9700 ?
C3 N2 . 1.4728(16) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 O2 . 1.2557(15) ?
C4 C5 3_776 1.4557(16) ?
C4 C5 . 1.4619(17) ?
C5 O3 . 1.2427(15) ?
C5 C4 3_776 1.4557(16) ?
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
N1 H1B O5 1_455 0.90 2.35 3.1715(16) 151.9
N2 H2A O2 3_676 0.90 2.33 3.2174(14) 170.4
O1 H1F O2 1_545 0.77(2) 2.08(2) 2.8345(15) 165(2)
O4 H4A O2 1_545 0.80(2) 2.10(2) 2.8765(16) 165(2)
O4 H4B O2 3_666 0.82(3) 2.07(3) 2.8965(16) 178(2)
O5 H5B O4 2_655 0.77(2) 2.10(3) 2.8730(19) 177(2)
N1 H1A O4 . 0.90 2.38 3.2442(17) 160.2
N2 H2B O3 . 0.90 2.04 2.9333(14) 173.5
O1 H1E O5 . 0.80(2) 1.93(2) 2.7311(16) 175.8(19)
O5 H5A O3 . 0.80(2) 1.94(2) 2.7296(16) 166(2)
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 Ni1 O1 . . . . -63.90(10) ?
C1 N1 Ni1 O1 . . . 3_666 116.10(10) ?
C1 N1 Ni1 N2 . . . 3_666 -152.47(10) ?
C1 N1 Ni1 N2 . . . . 27.53(10) ?
C3 N2 Ni1 O1 . . . . 60.31(10) ?
C3 N2 Ni1 O1 . . . 3_666 -119.69(10) ?
C2 C1 N1 Ni1 . . . . -50.38(16) ?
N1 C1 C2 C3 . . . . 72.93(17) ?
C1 C2 C3 N2 . . . . -73.63(16) ?
C2 C3 N2 Ni1 . . . . 52.35(14) ?
O2 C4 C5 O3 . . . . -0.2(3) ?
C5 C4 C5 O3 3_776 . . . 179.50(19) ?
O2 C4 C5 C4 . . . 3_776 -179.72(18) ?
C5 C4 C5 C4 3_776 . . 3_776 0.0 ?
