#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:22:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180335 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/04/7200448.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_7200448
loop_
_publ_author_name
'Koner, Rajesh'
'Goldberg, Israel'
_publ_section_title
;
 Supramolecular reactivity of naphthalene-1,4,5,8-tetracarboxylic acid
 towards transition metal ions: coordination polymers and discrete
 complexes with CuII, NiII and CoII
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              367
_journal_paper_doi               10.1039/b815885a
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C14 H24 Ni2 O18, 6(H2 O), (O)'
_chemical_formula_sum            'C14 H36 Ni2 O25'
_chemical_formula_weight         721.85
_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                113.7998(17)
_cell_angle_beta                 92.2836(16)
_cell_angle_gamma                107.734(2)
_cell_formula_units_Z            1
_cell_length_a                   7.7137(2)
_cell_length_b                   9.4183(3)
_cell_length_c                   11.4240(4)
_cell_measurement_reflns_used    2583
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.44
_cell_volume                     710.56(4)
_computing_cell_refinement       Denzo
_computing_data_collection       'Collect, Nonius B.V.'
_computing_data_reduction        'Denzo and Scalepack'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 12.8
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '1 deg. φ and ω 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  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7743
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         2.44
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.426
_exptl_absorpt_correction_T_max  0.8145
_exptl_absorpt_correction_T_min  0.6742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            'pale blue'
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.770
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3292
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0467
_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)+(0.0538P)²+0.8156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1144
_reflns_number_gt                2633
_reflns_number_total             3292
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b815885a.txt
_cod_data_source_block           Compound-7(ra8)
_cod_database_code               7200448
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Ni1 Ni 0.82490(5) 0.03162(5) -0.29710(3) 0.01687(13) Uani 1 1 d . . .
O2 O 0.7021(3) 0.1926(2) -0.18321(18) 0.0162(4) Uani 1 1 d . . .
C3 C 0.5517(4) 0.1475(3) -0.1449(3) 0.0153(6) Uani 1 1 d . . .
O4 O 0.4532(3) -0.0009(2) -0.1765(2) 0.0228(5) Uani 1 1 d . . .
C5 C 0.4950(4) 0.2816(3) -0.0477(3) 0.0147(5) Uani 1 1 d . . .
C6 C 0.4439(4) 0.2596(4) 0.0589(3) 0.0179(6) Uani 1 1 d . . .
H6 H 0.4223 0.1550 0.0594 0.021 Uiso 1 1 calc R . .
C7 C 0.4228(4) 0.3892(4) 0.1677(3) 0.0185(6) Uani 1 1 d . . .
H7 H 0.3863 0.3710 0.2404 0.022 Uiso 1 1 calc R . .
C8 C 0.4545(4) 0.5421(3) 0.1701(3) 0.0141(5) Uani 1 1 d . . .
C9 C 0.5098(4) 0.4338(3) -0.0555(3) 0.0133(5) Uani 1 1 d . . .
C10 C 0.4821(4) 0.6831(3) 0.3014(3) 0.0158(6) Uani 1 1 d . . .
O11 O 0.6249(3) 0.8099(2) 0.33143(19) 0.0199(4) Uani 1 1 d . . .
O12 O 0.3713(3) 0.6667(3) 0.37811(19) 0.0202(4) Uani 1 1 d . . .
O13 O 0.5854(3) -0.1788(2) -0.36461(19) 0.0198(4) Uani 1 1 d D . .
H13A H 0.5212 -0.1348 -0.3121 0.024 Uiso 1 1 d RD . .
H13B H 0.5270 -0.2156 -0.4413 0.024 Uiso 1 1 d RD . .
O14 O 0.7663(3) 0.0788(2) -0.45326(19) 0.0177(4) Uani 1 1 d D . .
H14A H 0.7201 0.1549 -0.4310 0.021 Uiso 1 1 d RD . .
H14B H 0.7132 -0.0071 -0.5237 0.021 Uiso 1 1 d RD . .
O15 O 0.8807(3) -0.0147(3) -0.1444(2) 0.0269(5) Uani 1 1 d D . .
H15A H 0.9695 -0.0495 -0.1412 0.032 Uiso 1 1 d RD . .
H15B H 0.8674 0.0433 -0.0683 0.032 Uiso 1 1 d RD . .
O16 O 0.9509(3) -0.1281(3) -0.4038(2) 0.0273(5) Uani 1 1 d D . .
H16A H 0.8930 -0.2320 -0.4369 0.033 Uiso 1 1 d RD . .
H16B H 1.0334 -0.1140 -0.4492 0.033 Uiso 1 1 d RD . .
O17 O 1.0672(3) 0.2358(3) -0.2345(2) 0.0263(5) Uani 1 1 d D . .
H17A H 1.1626 0.2142 -0.2585 0.032 Uiso 1 1 d RD . .
H17B H 1.0937 0.3056 -0.1557 0.032 Uiso 1 1 d RD . .
O18 O 0.8647(3) 0.1497(3) 0.1125(2) 0.0268(5) Uani 1 1 d D . .
H18A H 0.8971 0.2523 0.1621 0.032 Uiso 1 1 d RD . .
H18B H 0.7655 0.1027 0.1320 0.032 Uiso 1 1 d RD . .
O19 O 0.9879(4) 0.4926(4) 0.2705(4) 0.0684(10) Uani 1 1 d D . .
H19A H 1.1033 0.5432 0.3037 0.082 Uiso 1 1 d RD . .
H19B H 0.8834 0.4742 0.2953 0.082 Uiso 1 1 d RD . .
O20 O 0.7786(8) -0.4618(5) -0.5254(5) 0.134(2) Uani 1 1 d D . .
H20A H 0.8753 -0.4507 -0.4730 0.161 Uiso 1 1 d RD . .
H20B H 0.7021 -0.5568 -0.5407 0.161 Uiso 1 1 d RD . .
O21 O 0.0345(9) 0.4799(11) -0.0054(9) 0.061(2) Uani 0.50 1 d P . .
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'
Ni Ni 0.3393 1.1124 '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'
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
O15 Ni1 O16 89.03(9) . . ?
O15 Ni1 O2 88.87(8) . . ?
O16 Ni1 O2 177.84(8) . . ?
O15 Ni1 O14 179.68(8) . . ?
O16 Ni1 O14 91.19(8) . . ?
O2 Ni1 O14 90.91(8) . . ?
O15 Ni1 O17 92.22(9) . . ?
O16 Ni1 O17 92.93(9) . . ?
O2 Ni1 O17 86.65(8) . . ?
O14 Ni1 O17 88.01(8) . . ?
O15 Ni1 O13 88.11(9) . . ?
O16 Ni1 O13 85.14(9) . . ?
O2 Ni1 O13 95.29(8) . . ?
O14 Ni1 O13 91.68(8) . . ?
O17 Ni1 O13 178.04(8) . . ?
C3 O2 Ni1 124.10(17) . . ?
O4 C3 O2 124.6(3) . . ?
O4 C3 C5 118.0(2) . . ?
O2 C3 C5 117.2(2) . . ?
C6 C5 C9 120.1(2) . . ?
C6 C5 C3 115.9(2) . . ?
C9 C5 C3 123.7(2) . . ?
C5 C6 C7 121.1(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.1(3) . 2_665 ?
C7 C8 C10 116.2(2) . . ?
C9 C8 C10 122.8(2) 2_665 . ?
C9 C9 C8 118.8(3) 2_665 2_665 ?
C9 C9 C5 118.6(3) 2_665 . ?
C8 C9 C5 122.6(2) 2_665 . ?
O11 C10 O12 123.7(3) . . ?
O11 C10 C8 116.2(2) . . ?
O12 C10 C8 119.9(3) . . ?
Ni1 O13 H13A 96.6 . . ?
Ni1 O13 H13B 118.4 . . ?
H13A O13 H13B 107.5 . . ?
Ni1 O14 H14A 110.7 . . ?
Ni1 O14 H14B 114.4 . . ?
H14A O14 H14B 117.2 . . ?
Ni1 O15 H15A 118.6 . . ?
Ni1 O15 H15B 122.0 . . ?
H15A O15 H15B 111.0 . . ?
Ni1 O16 H16A 119.8 . . ?
Ni1 O16 H16B 129.4 . . ?
H16A O16 H16B 105.7 . . ?
Ni1 O17 H17A 115.0 . . ?
Ni1 O17 H17B 118.5 . . ?
H17A O17 H17B 109.8 . . ?
H18A O18 H18B 106.5 . . ?
H19A O19 H19B 139.2 . . ?
H20A O20 H20B 103.3 . . ?
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
Ni1 O15 2.022(2) . ?
Ni1 O16 2.049(2) . ?
Ni1 O2 2.0660(19) . ?
Ni1 O14 2.0695(19) . ?
Ni1 O17 2.073(2) . ?
Ni1 O13 2.087(2) . ?
O2 C3 1.268(3) . ?
C3 O4 1.259(3) . ?
C3 C5 1.505(4) . ?
C5 C6 1.369(4) . ?
C5 C9 1.442(4) . ?
C6 C7 1.405(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.374(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.439(4) 2_665 ?
C8 C10 1.501(4) . ?
C9 C9 1.429(5) 2_665 ?
C9 C8 1.439(4) 2_665 ?
C10 O11 1.262(4) . ?
C10 O12 1.270(3) . ?
O13 H13A 0.8511 . ?
O13 H13B 0.8484 . ?
O14 H14A 0.8493 . ?
O14 H14B 0.8467 . ?
O15 H15A 0.8498 . ?
O15 H15B 0.8502 . ?
O16 H16A 0.8500 . ?
O16 H16B 0.8489 . ?
O17 H17A 0.8485 . ?
O17 H17B 0.8428 . ?
O18 H18A 0.8464 . ?
O18 H18B 0.8477 . ?
O19 H19A 0.8560 . ?
O19 H19B 0.8559 . ?
O20 H20A 0.8903 . ?
O20 H20B 0.8504 . ?
O21 O21 0.730(10) 2_565 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O13 H13A O4 0.85 1.78 2.603(3) 163.0 .
O13 H13B O12 0.85 2.02 2.860(3) 171.9 1_544
O14 H14A O12 0.85 1.90 2.752(3) 177.1 2_665
O14 H14B O11 0.85 1.75 2.594(3) 173.9 1_544
O15 H15A O18 0.85 1.89 2.729(3) 167.0 2_755
O15 H15B O18 0.85 1.90 2.739(3) 168.2 .
O16 H16A O20 0.85 1.87 2.713(5) 173.6 .
O16 H16B O14 0.85 1.97 2.814(3) 177.2 2_754
O17 H17A O11 0.85 1.90 2.739(3) 168.6 2_765
O17 H17B O21 0.84 2.02 2.784(8) 149.6 1_655
O18 H18A O19 0.85 1.96 2.807(4) 175.7 .
O18 H18B O4 0.85 1.87 2.719(3) 179.5 2_655
O19 H19A O12 0.86 1.99 2.842(4) 177.9 1_655
O19 H19B O20 0.86 2.16 2.854(6) 138.5 1_566
O20 H20A O19 0.89 2.72 3.520(8) 149.6 2_755
O20 H20B O13 0.85 2.56 3.379(5) 161.6 2_644
