#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/74/2237412.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_2237412
loop_
_publ_author_name
'Qian, Qi-feng'
'Wu, Jin-hui'
'Qian, Jin-liang'
_publ_section_title
;
 [μ-6,9-Bis(carboxylatomethyl)-3,12-bis(carboxymethyl)-3,6,9,12-tetraazatetradecanedioato]bis[aquacobalt(II)]
 tetrahydrate
;
_journal_coeditor_code           TK5188
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m97
_journal_paper_doi               10.1107/S1600536813000196
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '[Co2 (C18 H26 N4 O12) (H2 O)2], 4H2 O'
_chemical_formula_moiety         'C18 H30 Co2 N4 O14, 4(H2 O)'
_chemical_formula_sum            'C18 H38 Co2 N4 O18'
_chemical_formula_weight         716.38
_chemical_name_systematic
;
[μ-6,9-Bis(carboxylatomethyl)-3,12-bis(carboxymethyl)-3,6,9,12-
tetraazatetradecanedioato]bis[aquacobalt(II)] tetrahydrate
;
_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                104.238(4)
_cell_angle_beta                 100.986(3)
_cell_angle_gamma                100.425(4)
_cell_formula_units_Z            1
_cell_length_a                   7.0972(15)
_cell_length_b                   8.7025(19)
_cell_length_c                   11.968(3)
_cell_measurement_reflns_used    1506
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      23.80
_cell_measurement_theta_min      2.62
_cell_volume                     682.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '0.3° wide ω exposures'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus sealed Siemens Mo tube'
_diffrn_radiation_type           'Mo k\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0969
_diffrn_reflns_av_sigmaI/netI    0.1075
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8012
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    1.305
_exptl_absorpt_correction_T_max  0.9376
_exptl_absorpt_correction_T_min  0.8805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008)'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.534
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0532
_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)+(0.0470P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1172
_reflns_number_gt                2182
_reflns_number_total             3099
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5188.cif
_cod_data_source_block           I
_cod_database_code               2237412
_cod_database_fobs_code          2237412
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
Co Co1 0.72982(7) 0.71114(6) 0.70687(4) 0.02486(17) Uani d . 1 1
N N1 0.9888(4) 0.6394(4) 0.6502(2) 0.0260(7) Uani d . 1 1
N N2 0.9015(4) 0.9540(4) 0.7434(2) 0.0255(7) Uani d . 1 1
O O1 1.0763(4) 0.5057(4) 0.9155(2) 0.0457(8) Uani d . 1 1
H H1 1.0240 0.5153 0.9715 0.069 Uiso calc PR 0.50 1
O O2 0.8739(4) 0.6544(3) 0.8584(2) 0.0306(6) Uani d . 1 1
O O3 0.6757(5) 0.9168(4) 0.4387(2) 0.0548(9) Uani d . 1 1
O O4 0.6154(4) 0.7492(3) 0.5486(2) 0.0308(6) Uani d . 1 1
O O5 0.6500(4) 1.0653(3) 0.9745(2) 0.0401(7) Uani d . 1 1
H H5 0.5449 1.0184 0.9830 0.060 Uiso calc PR 0.50 1
O O6 0.5890(4) 0.8431(3) 0.8222(2) 0.0335(6) Uani d . 1 1
O O7 0.5376(4) 0.4898(3) 0.6630(2) 0.0416(7) Uani d . 1 1
H H7A 0.5779 0.4274 0.6978 0.062 Uiso d R 1 1
H H7B 0.5143 0.4317 0.5943 0.062 Uiso d R 1 1
C C1 0.9172(5) 0.5213(5) 0.5288(3) 0.0322(9) Uani d . 1 1
H H1A 0.8342 0.5670 0.4781 0.039 Uiso calc R 1 1
H H1B 0.8362 0.4217 0.5334 0.039 Uiso calc R 1 1
C C2 1.0911(6) 0.5704(5) 0.7386(3) 0.0395(10) Uani d . 1 1
H H2A 1.2292 0.6286 0.7657 0.047 Uiso calc R 1 1
H H2B 1.0851 0.4570 0.7004 0.047 Uiso calc R 1 1
C C3 1.0033(6) 0.5803(5) 0.8454(3) 0.0302(9) Uani d . 1 1
C C4 1.1120(6) 0.7947(5) 0.6468(3) 0.0313(9) Uani d . 1 1
H H4A 1.0630 0.8154 0.5719 0.038 Uiso calc R 1 1
H H4B 1.2472 0.7852 0.6518 0.038 Uiso calc R 1 1
C C5 1.1076(6) 0.9363(5) 0.7487(3) 0.0351(10) Uani d . 1 1
H H5A 1.1622 0.9181 0.8237 0.042 Uiso calc R 1 1
H H5B 1.1887 1.0362 0.7446 0.042 Uiso calc R 1 1
C C6 0.8262(6) 1.0170(5) 0.6438(3) 0.0362(10) Uani d . 1 1
H H6A 0.9377 1.0745 0.6224 0.043 Uiso calc R 1 1
H H6B 0.7507 1.0950 0.6706 0.043 Uiso calc R 1 1
C C7 0.6972(6) 0.8852(5) 0.5344(3) 0.0330(9) Uani d . 1 1
C C8 0.8807(6) 1.0525(5) 0.8581(3) 0.0310(9) Uani d . 1 1
H H8A 0.8829 1.1632 0.8554 0.037 Uiso calc R 1 1
H H8B 0.9912 1.0565 0.9215 0.037 Uiso calc R 1 1
C C9 0.6896(6) 0.9799(5) 0.8838(3) 0.0284(8) Uani d . 1 1
O O8 0.5622(5) 0.2722(4) 0.7785(3) 0.0729(11) Uani d . 1 1
H H8C 0.5855 0.3176 0.8501 0.109 Uiso d R 1 1
H H8D 0.4441 0.2302 0.7658 0.109 Uiso d R 1 1
O O9 0.3797(6) 0.3141(5) 0.9602(4) 0.1021(15) Uani d . 1 1
H H9A 0.3722 0.2969 1.0237 0.153 Uiso d R 1 1
H H9B 0.2845 0.3520 0.9418 0.153 Uiso d R 1 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'
Co Co 0.3494 0.9721 '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
O7 Co1 O4 . . 92.28(11)
O7 Co1 O6 . . 97.80(11)
O4 Co1 O6 . . 102.38(10)
O7 Co1 O2 . . 87.25(11)
O4 Co1 O2 . . 172.02(10)
O6 Co1 O2 . . 85.56(10)
O7 Co1 N2 . . 172.89(11)
O4 Co1 N2 . . 82.40(11)
O6 Co1 N2 . . 78.85(11)
O2 Co1 N2 . . 98.68(11)
O7 Co1 N1 . . 100.97(11)
O4 Co1 N1 . . 93.72(10)
O6 Co1 N1 . . 154.68(11)
O2 Co1 N1 . . 78.57(10)
N2 Co1 N1 . . 84.15(11)
C2 N1 C4 . . 112.2(3)
C2 N1 C1 . . 112.8(3)
C4 N1 C1 . . 110.5(3)
C2 N1 Co1 . . 108.9(2)
C4 N1 Co1 . . 103.8(2)
C1 N1 Co1 . . 108.1(2)
C8 N2 C6 . . 111.9(3)
C8 N2 C5 . . 112.3(3)
C6 N2 C5 . . 111.7(3)
C8 N2 Co1 . . 108.2(2)
C6 N2 Co1 . . 107.5(2)
C5 N2 Co1 . . 104.7(2)
C3 O1 H1 . . 109.5
C3 O2 Co1 . . 116.4(2)
C7 O4 Co1 . . 115.5(2)
C9 O5 H5 . . 109.5
C9 O6 Co1 . . 114.6(2)
Co1 O7 H7A . . 113.6
Co1 O7 H7B . . 117.3
H7A O7 H7B . . 99.1
N1 C1 C1 . 2_766 113.9(4)
N1 C1 H1A . . 108.8
C1 C1 H1A 2_766 . 108.8
N1 C1 H1B . . 108.8
C1 C1 H1B 2_766 . 108.8
H1A C1 H1B . . 107.7
N1 C2 C3 . . 113.2(3)
N1 C2 H2A . . 108.9
C3 C2 H2A . . 108.9
N1 C2 H2B . . 108.9
C3 C2 H2B . . 108.9
H2A C2 H2B . . 107.7
O2 C3 O1 . . 125.6(3)
O2 C3 C2 . . 120.8(3)
O1 C3 C2 . . 113.6(3)
N1 C4 C5 . . 111.0(3)
N1 C4 H4A . . 109.4
C5 C4 H4A . . 109.4
N1 C4 H4B . . 109.4
C5 C4 H4B . . 109.4
H4A C4 H4B . . 108.0
N2 C5 C4 . . 110.7(3)
N2 C5 H5A . . 109.5
C4 C5 H5A . . 109.5
N2 C5 H5B . . 109.5
C4 C5 H5B . . 109.5
H5A C5 H5B . . 108.1
N2 C6 C7 . . 113.7(3)
N2 C6 H6A . . 108.8
C7 C6 H6A . . 108.8
N2 C6 H6B . . 108.8
C7 C6 H6B . . 108.8
H6A C6 H6B . . 107.7
O3 C7 O4 . . 124.8(4)
O3 C7 C6 . . 117.7(4)
O4 C7 C6 . . 117.5(3)
N2 C8 C9 . . 110.6(3)
N2 C8 H8A . . 109.5
C9 C8 H8A . . 109.5
N2 C8 H8B . . 109.5
C9 C8 H8B . . 109.5
H8A C8 H8B . . 108.1
O6 C9 O5 . . 124.5(4)
O6 C9 C8 . . 120.5(3)
O5 C9 C8 . . 114.9(3)
H8D O8 H8C . . 99.3
H8C O8 H8D . . 99.3
H9A O9 H9B . . 104.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Co1 O7 . 2.031(3)
Co1 O4 . 2.043(2)
Co1 O6 . 2.094(2)
Co1 O2 . 2.120(2)
Co1 N2 . 2.134(3)
Co1 N1 . 2.216(3)
N1 C2 . 1.477(4)
N1 C4 . 1.486(4)
N1 C1 . 1.490(4)
N2 C8 . 1.478(4)
N2 C6 . 1.480(4)
N2 C5 . 1.490(5)
O1 C3 . 1.272(4)
O1 H1 . 0.8200
O2 C3 . 1.226(4)
O3 C7 . 1.230(4)
O4 C7 . 1.286(4)
O5 C9 . 1.267(4)
O5 H5 . 0.8200
O6 C9 . 1.237(4)
O7 H7A . 0.8201
O7 H7B . 0.8200
C1 C1 2_766 1.527(7)
C1 H1A . 0.9700
C1 H1B . 0.9700
C2 C3 . 1.516(5)
C2 H2A . 0.9700
C2 H2B . 0.9700
C4 C5 . 1.515(5)
C4 H4A . 0.9700
C4 H4B . 0.9700
C5 H5A . 0.9700
C5 H5B . 0.9700
C6 C7 . 1.514(5)
C6 H6A . 0.9700
C6 H6B . 0.9700
C8 C9 . 1.509(5)
C8 H8A . 0.9700
C8 H8B . 0.9700
O8 H8D . 0.8200
O8 H8C . 0.8200
O8 H8D . 0.8200
O9 H9A . 0.8200
O9 H9B . 0.8200
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
_geom_hbond_publ_flag
O1 H1 O1 2_767 0.82 1.68 2.483(5) 168 y
O5 H5 O5 2_677 0.82 1.67 2.481(5) 170 y
O7 H7A O8 . 0.82 1.84 2.616(4) 157 y
O7 H7B O4 2_666 0.82 1.95 2.732(4) 159 y
O8 H8D O3 2_666 0.82 2.37 2.745(5) 109 y
O8 H8C O9 . 0.82 2.15 2.719(5) 127 y
O9 H9A O2 2_667 0.82 2.48 3.067(4) 130 y
O9 H9A O6 2_667 0.82 2.45 3.217(5) 157 y
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_4
_geom_torsion
O7 Co1 N1 C2 . -76.1(3)
O4 Co1 N1 C2 . -169.1(2)
O6 Co1 N1 C2 . 61.1(4)
O2 Co1 N1 C2 . 8.8(2)
N2 Co1 N1 C2 . 108.9(3)
O7 Co1 N1 C4 . 164.2(2)
O4 Co1 N1 C4 . 71.1(2)
O6 Co1 N1 C4 . -58.6(3)
O2 Co1 N1 C4 . -110.9(2)
N2 Co1 N1 C4 . -10.8(2)
O7 Co1 N1 C1 . 46.8(2)
O4 Co1 N1 C1 . -46.3(2)
O6 Co1 N1 C1 . -176.0(2)
O2 Co1 N1 C1 . 131.7(2)
N2 Co1 N1 C1 . -128.2(2)
O4 Co1 N2 C8 . 127.7(2)
O6 Co1 N2 C8 . 23.4(2)
O2 Co1 N2 C8 . -60.3(2)
N1 Co1 N2 C8 . -137.7(2)
O4 Co1 N2 C6 . 6.6(2)
O6 Co1 N2 C6 . -97.7(2)
O2 Co1 N2 C6 . 178.6(2)
N1 Co1 N2 C6 . 101.2(2)
O4 Co1 N2 C5 . -112.3(2)
O6 Co1 N2 C5 . 143.4(2)
O2 Co1 N2 C5 . 59.7(2)
N1 Co1 N2 C5 . -17.8(2)
O7 Co1 O2 C3 . 88.1(3)
O6 Co1 O2 C3 . -173.8(3)
N2 Co1 O2 C3 . -95.8(3)
N1 Co1 O2 C3 . -13.7(3)
O7 Co1 O4 C7 . -179.9(3)
O6 Co1 O4 C7 . 81.6(3)
N2 Co1 O4 C7 . 4.8(3)
N1 Co1 O4 C7 . -78.8(3)
O7 Co1 O6 C9 . 166.7(3)
O4 Co1 O6 C9 . -99.2(3)
O2 Co1 O6 C9 . 80.1(3)
N2 Co1 O6 C9 . -19.6(3)
N1 Co1 O6 C9 . 29.1(4)
C2 N1 C1 C1 2_766 -67.4(5)
C4 N1 C1 C1 2_766 59.1(5)
Co1 N1 C1 C1 2_766 172.2(4)
C4 N1 C2 C3 . 109.8(4)
C1 N1 C2 C3 . -124.6(3)
Co1 N1 C2 C3 . -4.6(4)
Co1 O2 C3 O1 . -164.1(3)
Co1 O2 C3 C2 . 15.6(5)
N1 C2 C3 O2 . -6.9(5)
N1 C2 C3 O1 . 172.8(3)
C2 N1 C4 C5 . -79.2(4)
C1 N1 C4 C5 . 154.0(3)
Co1 N1 C4 C5 . 38.2(3)
C8 N2 C5 C4 . 161.8(3)
C6 N2 C5 C4 . -71.5(4)
Co1 N2 C5 C4 . 44.6(3)
N1 C4 C5 N2 . -59.1(4)
C8 N2 C6 C7 . -134.5(3)
C5 N2 C6 C7 . 98.6(4)
Co1 N2 C6 C7 . -15.7(4)
Co1 O4 C7 O3 . 165.6(3)
Co1 O4 C7 C6 . -15.6(4)
N2 C6 C7 O3 . -159.4(4)
N2 C6 C7 O4 . 21.6(5)
C6 N2 C8 C9 . 93.7(4)
C5 N2 C8 C9 . -139.8(3)
Co1 N2 C8 C9 . -24.7(3)
Co1 O6 C9 O5 . -165.2(3)
Co1 O6 C9 C8 . 10.9(4)
N2 C8 C9 O6 . 10.2(5)
N2 C8 C9 O5 . -173.3(3)
