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#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/43/7004369.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_7004369
loop_
_publ_author_name
'Harjani, Jitendra R.'
'Friščić, Tomislav'
'MacGillivray, Leonard R.'
'Singer, Robert D.'
_publ_section_title
;
 Removal of metal ions from aqueous solutions using chelating
 task-specific ionic liquids
;
_journal_issue                   34
_journal_name_full               'Dalton Transactions'
_journal_page_first              4595
_journal_paper_doi               10.1039/b806369a
_journal_year                    2008
_chemical_formula_moiety         'C20 H28 N6 Ni O8, 2(H2 O)'
_chemical_formula_sum            'C20 H32 N6 Ni O10'
_chemical_formula_weight         575.23
_chemical_name_common            'Ni(EDA-mim)2 dihydrate'
_chemical_name_systematic
;
Ni(EDA-mim)2 dihydrate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2988(11)
_cell_length_b                   10.0381(10)
_cell_length_c                   21.557(2)
_cell_measurement_reflns_used    10018
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     2445.0(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD phi and omega 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  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18585
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.861
_exptl_absorpt_correction_T_max  0.8604
_exptl_absorpt_correction_T_min  0.7246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0319
_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)+(0.0591P)²+0.5751P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.1073
_reflns_number_gt                2187
_reflns_number_total             2802
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b806369a.txt
_cod_data_source_block           Ni
_cod_original_sg_symbol_H-M      Pbca
_cod_original_formula_sum        'C20 H32 N6 Ni1 O10'
_cod_database_code               7004369
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni 0.0000 0.0000 0.5000 0.01535(13) Uani 1 2 d S . .
O1 O 0.08510(12) 0.08492(13) 0.42750(6) 0.0242(3) Uani 1 1 d . . .
O2 O 0.10495(14) 0.27746(15) 0.37744(7) 0.0365(4) Uani 1 1 d . . .
O3 O -0.14354(13) -0.03106(14) 0.44210(7) 0.0258(3) Uani 1 1 d . . .
O4 O -0.31112(14) 0.06338(16) 0.41145(9) 0.0446(5) Uani 1 1 d . . .
O5 O -0.2292(2) -0.1967(2) 0.33779(9) 0.0729(7) Uani 1 1 d . . .
N1 N -0.07914(13) 0.18896(15) 0.51023(7) 0.0159(3) Uani 1 1 d . . .
N2 N -0.10988(14) 0.40754(15) 0.65242(7) 0.0215(4) Uani 1 1 d . . .
N3 N -0.04111(18) 0.48622(17) 0.73797(9) 0.0275(4) Uani 1 1 d . . .
C1 C -0.01595(16) 0.27802(19) 0.46652(9) 0.0221(4) Uani 1 1 d . . .
H1A H 0.0335 0.3405 0.4909 0.026 Uiso 1 1 calc R . .
H1B H -0.0753 0.3316 0.4438 0.026 Uiso 1 1 calc R . .
C2 C 0.06323(16) 0.20753(19) 0.41918(9) 0.0212(4) Uani 1 1 d . . .
C3 C -0.20448(16) 0.16916(19) 0.49213(9) 0.0209(4) Uani 1 1 d . . .
H3A H -0.2359 0.2536 0.4751 0.025 Uiso 1 1 calc R . .
H3B H -0.2512 0.1467 0.5295 0.025 Uiso 1 1 calc R . .
C4 C -0.22050(17) 0.05925(19) 0.44408(9) 0.0227(4) Uani 1 1 d . . .
C5 C -0.06923(17) 0.23545(19) 0.57507(8) 0.0201(4) Uani 1 1 d . . .
H5A H 0.0154 0.2357 0.5870 0.024 Uiso 1 1 calc R . .
H5B H -0.1106 0.1712 0.6024 0.024 Uiso 1 1 calc R . .
C6 C -0.12047(17) 0.37475(19) 0.58647(8) 0.0221(4) Uani 1 1 d . . .
H6A H -0.0769 0.4412 0.5613 0.027 Uiso 1 1 calc R . .
H6B H -0.2047 0.3769 0.5739 0.027 Uiso 1 1 calc R . .
C7 C -0.02171(18) 0.4766(2) 0.67788(10) 0.0230(4) Uani 1 1 d . . .
H7 H 0.0441 0.5129 0.6563 0.028 Uiso 1 1 calc R . .
C8 C -0.1453(2) 0.4207(2) 0.75190(11) 0.0385(6) Uani 1 1 d . . .
H8 H -0.1802 0.4121 0.7918 0.046 Uiso 1 1 calc R . .
C9 C -0.18793(19) 0.3715(2) 0.69842(10) 0.0326(5) Uani 1 1 d . . .
H9 H -0.2586 0.3213 0.6933 0.039 Uiso 1 1 calc R . .
C10 C 0.0320(2) 0.5612(3) 0.78189(11) 0.0418(6) Uani 1 1 d . . .
H10A H 0.1049 0.5903 0.7612 0.063 Uiso 1 1 calc R . .
H10B H 0.0521 0.5042 0.8173 0.063 Uiso 1 1 calc R . .
H10C H -0.0119 0.6393 0.7965 0.063 Uiso 1 1 calc R . .
H1O H -0.2105 -0.1332 0.3681 0.143 Uiso 1 1 d . . .
H2O H -0.2128 -0.2760 0.3619 0.143 Uiso 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni O1 180.0 5_556 . ?
O1 Ni O3 88.29(6) 5_556 5_556 ?
O1 Ni O3 91.71(6) . 5_556 ?
O1 Ni O3 91.71(6) 5_556 . ?
O1 Ni O3 88.29(6) . . ?
O3 Ni O3 180.0 5_556 . ?
O1 Ni N1 95.55(5) 5_556 . ?
O1 Ni N1 84.45(5) . . ?
O3 Ni N1 97.68(5) 5_556 . ?
O3 Ni N1 82.32(5) . . ?
O1 Ni N1 84.45(5) 5_556 5_556 ?
O1 Ni N1 95.55(5) . 5_556 ?
O3 Ni N1 82.32(5) 5_556 5_556 ?
O3 Ni N1 97.68(5) . 5_556 ?
N1 Ni N1 180.000(1) . 5_556 ?
C2 O1 Ni 115.19(12) . . ?
C4 O3 Ni 114.39(12) . . ?
H1O O5 H2O 98.14(18) . . ?
C5 N1 C1 111.98(15) . . ?
C5 N1 C3 111.33(14) . . ?
C1 N1 C3 111.95(14) . . ?
C5 N1 Ni 110.54(11) . . ?
C1 N1 Ni 105.77(11) . . ?
C3 N1 Ni 104.89(11) . . ?
C7 N2 C9 108.62(17) . . ?
C7 N2 C6 125.32(17) . . ?
C9 N2 C6 126.05(17) . . ?
C7 N3 C8 108.71(19) . . ?
C7 N3 C10 125.4(2) . . ?
C8 N3 C10 125.8(2) . . ?
N1 C1 C2 115.26(16) . . ?
N1 C1 H1A 108.5 . . ?
C2 C1 H1A 108.5 . . ?
N1 C1 H1B 108.5 . . ?
C2 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
O2 C2 O1 125.48(18) . . ?
O2 C2 C1 116.51(17) . . ?
O1 C2 C1 117.92(17) . . ?
N1 C3 C4 112.92(15) . . ?
N1 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
N1 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
O4 C4 O3 125.08(19) . . ?
O4 C4 C3 117.28(17) . . ?
O3 C4 C3 117.58(17) . . ?
N1 C5 C6 114.26(15) . . ?
N1 C5 H5A 108.7 . . ?
C6 C5 H5A 108.7 . . ?
N1 C5 H5B 108.7 . . ?
C6 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
N2 C6 C5 109.25(15) . . ?
N2 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
N3 C7 N2 108.58(19) . . ?
N3 C7 H7 125.7 . . ?
N2 C7 H7 125.7 . . ?
C9 C8 N3 107.11(19) . . ?
C9 C8 H8 126.4 . . ?
N3 C8 H8 126.4 . . ?
C8 C9 N2 106.96(19) . . ?
C8 C9 H9 126.5 . . ?
N2 C9 H9 126.5 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
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 2.0232(13) 5_556 ?
Ni O1 2.0232(13) . ?
Ni O3 2.0701(14) 5_556 ?
Ni O3 2.0701(14) . ?
Ni N1 2.1086(15) . ?
Ni N1 2.1086(15) 5_556 ?
O1 C2 1.268(2) . ?
O2 C2 1.235(2) . ?
O3 C4 1.257(2) . ?
O4 C4 1.243(2) . ?
O5 H1O 0.9368(19) . ?
O5 H2O 0.969(2) . ?
N1 C5 1.478(2) . ?
N1 C1 1.482(2) . ?
N1 C3 1.482(2) . ?
N2 C7 1.332(3) . ?
N2 C9 1.376(3) . ?
N2 C6 1.464(2) . ?
N3 C7 1.317(3) . ?
N3 C8 1.381(3) . ?
N3 C10 1.465(3) . ?
C1 C2 1.530(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C3 C4 1.524(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C6 1.533(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7 0.9500 . ?
C8 C9 1.344(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 Ni O1 C2 -95.01(13) 5_556 . . . ?
O3 Ni O1 C2 84.99(13) . . . . ?
N1 Ni O1 C2 2.54(13) . . . . ?
N1 Ni O1 C2 -177.46(13) 5_556 . . . ?
O1 Ni O3 C4 86.00(15) 5_556 . . . ?
O1 Ni O3 C4 -94.00(15) . . . . ?
N1 Ni O3 C4 -9.36(14) . . . . ?
N1 Ni O3 C4 170.64(14) 5_556 . . . ?
O1 Ni N1 C5 50.29(12) 5_556 . . . ?
O1 Ni N1 C5 -129.71(12) . . . . ?
O3 Ni N1 C5 -38.72(12) 5_556 . . . ?
O3 Ni N1 C5 141.28(12) . . . . ?
O1 Ni N1 C1 171.71(11) 5_556 . . . ?
O1 Ni N1 C1 -8.29(11) . . . . ?
O3 Ni N1 C1 82.69(11) 5_556 . . . ?
O3 Ni N1 C1 -97.31(11) . . . . ?
O1 Ni N1 C3 -69.81(11) 5_556 . . . ?
O1 Ni N1 C3 110.19(11) . . . . ?
O3 Ni N1 C3 -158.82(11) 5_556 . . . ?
O3 Ni N1 C3 21.18(11) . . . . ?
C5 N1 C1 C2 133.06(16) . . . . ?
C3 N1 C1 C2 -101.09(18) . . . . ?
Ni N1 C1 C2 12.59(18) . . . . ?
Ni O1 C2 O2 -179.32(16) . . . . ?
Ni O1 C2 C1 4.3(2) . . . . ?
N1 C1 C2 O2 171.13(17) . . . . ?
N1 C1 C2 O1 -12.1(2) . . . . ?
C5 N1 C3 C4 -149.43(16) . . . . ?
C1 N1 C3 C4 84.37(19) . . . . ?
Ni N1 C3 C4 -29.85(17) . . . . ?
Ni O3 C4 O4 176.96(18) . . . . ?
Ni O3 C4 C3 -5.9(2) . . . . ?
N1 C3 C4 O4 -156.91(18) . . . . ?
N1 C3 C4 O3 25.7(2) . . . . ?
C1 N1 C5 C6 60.2(2) . . . . ?
C3 N1 C5 C6 -66.0(2) . . . . ?
Ni N1 C5 C6 177.87(13) . . . . ?
C7 N2 C6 C5 95.1(2) . . . . ?
C9 N2 C6 C5 -84.3(2) . . . . ?
N1 C5 C6 N2 177.77(15) . . . . ?
C8 N3 C7 N2 0.2(2) . . . . ?
C10 N3 C7 N2 -176.3(2) . . . . ?
C9 N2 C7 N3 -0.3(2) . . . . ?
C6 N2 C7 N3 -179.69(17) . . . . ?
C7 N3 C8 C9 0.0(3) . . . . ?
C10 N3 C8 C9 176.4(2) . . . . ?
N3 C8 C9 N2 -0.1(3) . . . . ?
C7 N2 C9 C8 0.3(2) . . . . ?
C6 N2 C9 C8 179.67(19) . . . . ?
