#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/32/2203208.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_2203208
loop_
_publ_author_name
'Yeşilel, Okan Zafer '
'Bulut, Ahmet'
'Uçar, İbrahim'
'İçbudak, Hasan'
'Ölmez, Halis'
'Büyükgüngör, Orhan'
_publ_section_title
;
 Bis(triethanolamine-κ³N,O,O')nickel(II) squarate
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m228
_journal_page_last               m230
_journal_paper_doi               10.1107/S1600536804001503
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          '[Ni (C6 H15 N O3)2] (C4 O4)'
_chemical_formula_moiety         'C12 H30 N2 Ni O6 2+, C4 O4 2-'
_chemical_formula_sum            'C16 H30 N2 Ni O10'
_chemical_formula_weight         469.13
_chemical_name_systematic        ?
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.551(7)
_cell_angle_beta                 110.398(7)
_cell_angle_gamma                99.698(7)
_cell_formula_units_Z            1
_cell_length_a                   7.5058(7)
_cell_length_b                   8.5766(8)
_cell_length_c                   8.9156(8)
_cell_measurement_reflns_used    15818
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.11
_cell_measurement_theta_min      0.00
_cell_volume                     506.04(9)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  ' Stoe IPDS-2'
_diffrn_measurement_method       'ω rotation'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6624
_diffrn_reflns_theta_full        32.17
_diffrn_reflns_theta_max         32.17
_diffrn_reflns_theta_min         2.52
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.015
_exptl_absorpt_correction_T_max  0.7716
_exptl_absorpt_correction_T_min  0.5162
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour            Violet
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.573
_refine_ls_extinction_coef       0.108(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3549
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0472P)²+0.0971P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0894
_reflns_number_gt                3346
_reflns_number_total             3549
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na6286.cif
_cod_data_source_block           I
_cod_database_code               2203208
_cod_database_fobs_code          2203208
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
C8 0.9171(2) 0.2024(2) 0.6449(2) 0.0469(3) Uani d . 1 C
H8A 0.8991 0.0913 0.5772 0.056 Uiso calc R 1 H
H8B 1.0229 0.2757 0.6347 0.056 Uiso calc R 1 H
C7 0.7286(2) 0.25447(18) 0.57306(18) 0.0364(3) Uani d . 1 C
H7A 0.7045 0.2506 0.4580 0.044 Uiso calc R 1 H
H7B 0.6205 0.1721 0.5699 0.044 Uiso calc R 1 H
Ni1 0.5000 0.5000 0.5000 0.02565(8) Uani d S 1 Ni
O5 0.9764(2) 0.20398(19) 0.81404(19) 0.0547(3) Uani d . 1 O
N1 0.72030(15) 0.42007(14) 0.66026(13) 0.03006(19) Uani d . 1 N
C6 0.9044(2) 0.54865(19) 0.7057(2) 0.0394(3) Uani d . 1 C
H6A 0.9413 0.5360 0.6106 0.047 Uiso calc R 1 H
H6B 1.0098 0.5336 0.7975 0.047 Uiso calc R 1 H
O4 0.69503(15) 0.72964(12) 0.64365(13) 0.0355(2) Uani d . 1 O
O3 0.36826(14) 0.48024(12) 0.66497(12) 0.03259(18) Uani d . 1 O
C5 0.8806(2) 0.72131(19) 0.7572(2) 0.0464(3) Uani d . 1 C
H5A 0.8860 0.7477 0.8704 0.056 Uiso calc R 1 H
H5B 0.9871 0.8015 0.7554 0.056 Uiso calc R 1 H
C3 0.4506(2) 0.37127(18) 0.75402(18) 0.0365(3) Uani d . 1 C
H3A 0.3945 0.2576 0.6822 0.044 Uiso calc R 1 H
H3B 0.4189 0.3800 0.8516 0.044 Uiso calc R 1 H
C4 0.6719(2) 0.4173(2) 0.80839(17) 0.0373(3) Uani d . 1 C
H4A 0.7299 0.5255 0.8916 0.045 Uiso calc R 1 H
H4B 0.7264 0.3372 0.8587 0.045 Uiso calc R 1 H
O1 0.6483(2) 0.99418(13) 0.81537(16) 0.0471(3) Uani d . 1 O
O2 0.36287(18) 0.72086(12) 0.88896(15) 0.0432(2) Uani d . 1 O
C1 0.5674(2) 0.99736(15) 0.91714(16) 0.0332(2) Uani d . 1 C
C2 0.4384(2) 0.87302(15) 0.94906(16) 0.0320(2) Uani d . 1 C
H5 0.888(4) 0.145(3) 0.824(3) 0.067(8) Uiso d . 1 H
H4 0.667(3) 0.797(3) 0.691(3) 0.050(6) Uiso d . 1 H
H3 0.377(3) 0.561(3) 0.731(3) 0.047(5) Uiso d . 1 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'
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_publ_flag
O5 C8 C7 115.40(14) ?
O5 C8 H8A 108.4 ?
C7 C8 H8A 108.4 ?
O5 C8 H8B 108.4 ?
C7 C8 H8B 108.4 ?
H8A C8 H8B 107.5 ?
N1 C7 C8 117.90(13) ?
N1 C7 H7A 107.8 ?
C8 C7 H7A 107.8 ?
N1 C7 H7B 107.8 ?
C8 C7 H7B 107.8 ?
H7A C7 H7B 107.2 ?
O3 Ni1 O4 95.64(4) yes
O3 Ni1 N1 84.26(4) yes
O4 Ni1 N1 81.63(4) yes
C8 O5 H5 109(2) ?
C6 N1 C7 111.31(11) ?
C6 N1 C4 111.79(11) ?
C7 N1 C4 111.87(11) ?
C6 N1 Ni1 104.10(8) ?
C7 N1 Ni1 110.85(8) ?
C4 N1 Ni1 106.56(8) ?
N1 C6 C5 111.61(12) ?
N1 C6 H6A 109.3 ?
C5 C6 H6A 109.3 ?
N1 C6 H6B 109.3 ?
C5 C6 H6B 109.3 ?
H6A C6 H6B 108.0 ?
C5 O4 Ni1 113.84(9) ?
C5 O4 H4 105.9(18) ?
Ni1 O4 H4 123.1(19) ?
C3 O3 Ni1 106.95(7) ?
C3 O3 H3 107.6(16) ?
Ni1 O3 H3 118.8(16) ?
O4 C5 C6 109.37(12) ?
O4 C5 H5A 109.8 ?
C6 C5 H5A 109.8 ?
O4 C5 H5B 109.8 ?
C6 C5 H5B 109.8 ?
H5A C5 H5B 108.2 ?
O3 C3 C4 109.65(11) ?
O3 C3 H3A 109.7 ?
C4 C3 H3A 109.7 ?
O3 C3 H3B 109.7 ?
C4 C3 H3B 109.7 ?
H3A C3 H3B 108.2 ?
N1 C4 C3 109.60(11) ?
N1 C4 H4A 109.8 ?
C3 C4 H4A 109.8 ?
N1 C4 H4B 109.8 ?
C3 C4 H4B 109.8 ?
H4A C4 H4B 108.2 ?
O1 C1 C2 134.71(12) ?
O2 C2 C1 135.95(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C8 O5 1.412(2) ?
C8 C7 1.522(2) ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C7 N1 1.4863(17) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
Ni1 O3 2.0581(9) yes
Ni1 O4 2.0707(10) yes
Ni1 N1 2.0992(11) yes
O5 H5 0.81(3) ?
N1 C6 1.4805(18) ?
N1 C4 1.4907(17) ?
C6 C5 1.512(2) ?
C6 H6A 0.9700 ?
C6 H6B 0.9700 ?
O4 C5 1.4324(18) ?
O4 H4 0.75(2) ?
O3 C3 1.4357(17) ?
O3 H3 0.78(2) ?
C5 H5A 0.9700 ?
C5 H5B 0.9700 ?
C3 C4 1.511(2) ?
C3 H3A 0.9700 ?
C3 H3B 0.9700 ?
C4 H4A 0.9700 ?
C4 H4B 0.9700 ?
O1 C1 1.2537(15) yes
O2 C2 1.2437(16) yes
C1 C2 1.4604(18) yes
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
O5 H5 O1 1_545 0.81(3) 2.00(3) 2.8000(19) 172(3)
O3 H3 O2 . 0.78(2) 1.79(2) 2.5579(14) 169(2)
O4 H4 O1 . 0.75(2) 1.86(2) 2.5976(14) 168(3)
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
O5 C8 C7 N1 56.6(2)
C8 C7 N1 C6 44.45(16)
C8 C7 N1 C4 -81.42(15)
C8 C7 N1 Ni1 159.80(11)
O3 Ni1 N1 C6 -125.67(9)
O4 Ni1 N1 C6 -29.08(9)
O3 Ni1 N1 C7 114.56(9)
O4 Ni1 N1 C7 -148.85(9)
O3 Ni1 N1 C4 -7.38(9)
O4 Ni1 N1 C4 89.21(9)
C7 N1 C6 C5 166.79(12)
C4 N1 C6 C5 -67.30(15)
Ni1 N1 C6 C5 47.33(14)
O3 Ni1 O4 C5 90.78(11)
N1 Ni1 O4 C5 7.45(11)
O4 Ni1 O3 C3 -101.60(9)
N1 Ni1 O3 C3 -20.63(9)
Ni1 O4 C5 C6 16.29(17)
N1 C6 C5 O4 -43.35(18)
Ni1 O3 C3 C4 45.02(12)
C6 N1 C4 C3 146.32(12)
C7 N1 C4 C3 -88.08(13)
Ni1 N1 C4 C3 33.21(13)
O3 C3 C4 N1 -53.80(15)
O1 C1 C2 O2 0.4(3)
