#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/04/7200446.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_7200446
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         'C17 H18 N2 Ni O7, 5(H2 O), 0.5(C5 H5 N)'
_chemical_formula_sum            'C19.5 H30.5 N2.5 Ni O12'
_chemical_formula_weight         550.67
_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                110.7114(9)
_cell_angle_beta                 107.1917(12)
_cell_angle_gamma                100.4112(13)
_cell_formula_units_Z            2
_cell_length_a                   10.1872(2)
_cell_length_b                   11.3944(3)
_cell_length_c                   13.2253(4)
_cell_measurement_reflns_used    4581
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.47
_cell_volume                     1300.02(6)
_computing_cell_refinement       Denzo
_computing_data_collection       'Collect, Nonius B.V.'
_computing_data_reduction        'Denzo & Scalepack'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 12.8
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13325
_diffrn_reflns_theta_full        27.85
_diffrn_reflns_theta_max         27.85
_diffrn_reflns_theta_min         2.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  0.9236
_exptl_absorpt_correction_T_min  0.7936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             578
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.172
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0562
_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)+(0.0273P)²+4.3557P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1403
_reflns_number_gt                5267
_reflns_number_total             5976
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b815885a.txt
_cod_data_source_block           Compound-6(ra5)
_cod_original_formula_sum        'C19.50 H30.50 N2.50 Ni O12'
_cod_database_code               7200446
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 0.17247(4) 0.30579(4) 0.86569(4) 0.01220(12) Uani 1 1 d . . .
O2 O 0.3039(3) 0.1961(2) 0.9002(2) 0.0151(5) Uani 1 1 d . . .
C3 C 0.3770(4) 0.1466(3) 0.8439(3) 0.0156(6) Uani 1 1 d . . .
O4 O 0.3945(3) 0.1680(2) 0.7608(2) 0.0211(5) Uani 1 1 d . . .
C5 C 0.4343(3) 0.0452(3) 0.8743(3) 0.0146(6) Uani 1 1 d . . .
C6 C 0.4111(4) -0.0708(3) 0.7804(3) 0.0183(7) Uani 1 1 d . . .
H6 H 0.3845 -0.0747 0.7038 0.022 Uiso 1 1 d R . .
C7 C 0.4915(3) 0.0575(3) 0.9913(3) 0.0136(6) Uani 1 1 d . . .
C8 C 0.5343(3) 0.1801(3) 1.0927(3) 0.0143(6) Uani 1 1 d . . .
C9 C 0.5734(4) 0.1838(3) 1.2028(3) 0.0177(7) Uani 1 1 d . . .
H9 H 0.5900 0.2633 1.2683 0.021 Uiso 1 1 d R . .
C10 C 0.5605(3) 0.3115(3) 1.0864(3) 0.0160(6) Uani 1 1 d . . .
O11 O 0.5282(3) 0.4029(2) 1.1536(2) 0.0162(5) Uani 1 1 d . . .
O12 O 0.6215(3) 0.3252(2) 1.0203(3) 0.0250(6) Uani 1 1 d . . .
N13 N 0.0682(3) 0.2486(3) 0.9632(3) 0.0166(6) Uani 1 1 d . . .
C14 C 0.1415(4) 0.2349(4) 1.0582(3) 0.0216(7) Uani 1 1 d . . .
H14 H 0.2437 0.2548 1.0826 0.026 Uiso 1 1 calc R . .
C15 C 0.0749(5) 0.1927(4) 1.1228(4) 0.0326(9) Uani 1 1 d . . .
H15 H 0.1304 0.1846 1.1903 0.039 Uiso 1 1 calc R . .
C16 C -0.0741(5) 0.1627(5) 1.0863(5) 0.0408(11) Uani 1 1 d . . .
H16 H -0.1226 0.1346 1.1290 0.049 Uiso 1 1 calc R . .
C17 C -0.1511(5) 0.1742(5) 0.9871(5) 0.0370(10) Uani 1 1 d . . .
H17 H -0.2536 0.1527 0.9598 0.044 Uiso 1 1 calc R . .
C18 C -0.0767(4) 0.2176(4) 0.9282(4) 0.0288(9) Uani 1 1 d . . .
H18 H -0.1301 0.2257 0.8602 0.035 Uiso 1 1 calc R . .
N19 N 0.0234(3) 0.1438(3) 0.7142(3) 0.0213(6) Uani 1 1 d . . .
C20 C -0.0572(4) 0.1536(5) 0.6196(3) 0.0298(9) Uani 1 1 d . . .
H20 H -0.0444 0.2384 0.6199 0.036 Uiso 1 1 calc R . .
C21 C -0.1605(4) 0.0426(6) 0.5197(4) 0.0277(13) Uani 1 1 d . . .
H21 H -0.2167 0.0524 0.4535 0.053 Uiso 1 1 calc R . .
C22 C -0.1795(5) -0.0795(5) 0.5186(4) 0.0287(14) Uani 1 1 d . . .
H22 H -0.2496 -0.1556 0.4519 0.058 Uiso 1 1 calc R . .
C23 C -0.0960(5) -0.0911(5) 0.6150(4) 0.0251(12) Uani 1 1 d . . .
H23 H -0.1064 -0.1753 0.6157 0.050 Uiso 1 1 calc R . .
C24 C 0.0036(5) 0.0222(4) 0.7110(3) 0.0289(9) Uani 1 1 d . . .
H24 H 0.0606 0.0138 0.7777 0.035 Uiso 1 1 calc R . .
O25 O 0.2724(2) 0.3546(2) 0.7632(2) 0.0146(5) Uani 1 1 d . . .
H25A H 0.3236 0.2976 0.7572 0.022 Uiso 1 1 d R . .
H25B H 0.3396 0.4345 0.7952 0.022 Uiso 1 1 d R . .
O26 O 0.3189(3) 0.4694(2) 1.0198(2) 0.0156(5) Uani 1 1 d . . .
H26A H 0.3528 0.5380 1.0059 0.023 Uiso 1 1 d R . .
H26B H 0.4041 0.4628 1.0574 0.023 Uiso 1 1 d R . .
O27 O 0.0621(3) 0.4385(3) 0.8413(3) 0.0274(6) Uani 1 1 d . . .
H27A H -0.0306 0.4351 0.8304 0.041 Uiso 1 1 d R . .
H27B H 0.1134 0.5249 0.8867 0.041 Uiso 1 1 d R . .
O28 O 0.2202(3) 0.5755(2) 0.2000(2) 0.0217(5) Uani 1 1 d . . .
H28A H 0.2485 0.5472 0.1400 0.033 Uiso 1 1 d R . .
H28B H 0.2753 0.6600 0.2290 0.033 Uiso 1 1 d R . .
O29 O 0.5020(3) 0.1309(3) 0.4528(2) 0.0301(6) Uani 1 1 d . . .
H29A H 0.4349 0.0504 0.4152 0.045 Uiso 1 1 d R . .
H29B H 0.4538 0.1874 0.4431 0.045 Uiso 1 1 d R . .
O30 O 0.4147(3) 0.4736(3) 0.3226(2) 0.0286(6) Uani 1 1 d . . .
H30A H 0.4592 0.4523 0.2727 0.043 Uiso 1 1 d R . .
H30B H 0.3516 0.5184 0.3137 0.043 Uiso 1 1 d R . .
O31 O 0.3862(3) 0.8413(3) 0.3195(2) 0.0259(6) Uani 1 1 d . . .
H31A H 0.4583 0.8453 0.2937 0.039 Uiso 1 1 d R . .
H31B H 0.4311 0.8523 0.3934 0.039 Uiso 1 1 d R . .
O32 O 0.3841(3) 0.3330(3) 0.4560(3) 0.0323(6) Uani 1 1 d . . .
H32A H 0.4438 0.3996 0.5265 0.049 Uiso 1 1 d R . .
H32B H 0.4131 0.3601 0.4079 0.049 Uiso 1 1 d R . .
C33 C -0.1096(12) 0.5452(11) 0.4364(11) 0.035(2) Uani 0.50 1 d P . .
H33 H -0.1966 0.5784 0.4109 0.042 Uiso 0.50 1 d PR . .
C34 C -0.0750(14) 0.5375(11) 0.5437(13) 0.036(2) Uani 0.50 1 d P . .
H34 H -0.1314 0.5581 0.5893 0.043 Uiso 0.50 1 d PR . .
C35 C 0.0440(13) 0.4981(11) 0.5816(10) 0.039(2) Uani 0.50 1 d P . .
H35 H 0.0689 0.4917 0.6542 0.047 Uiso 0.50 1 d PR . .
C36 C 0.1244(13) 0.4731(10) 0.5132(14) 0.034(2) Uani 0.50 1 d P . .
H36 H 0.2058 0.4462 0.5401 0.041 Uiso 0.50 1 d PR . .
C37 C 0.0832(10) 0.4834(9) 0.4081(10) 0.0297(18) Uani 0.50 1 d P . .
H37 H 0.1396 0.4628 0.3625 0.036 Uiso 0.50 1 d PR . .
N38 N -0.0329(8) 0.5206(8) 0.3695(8) 0.0301(15) 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'
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'
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
O2 Ni1 N19 91.71(11) . . ?
O2 Ni1 O25 91.94(9) . . ?
N19 Ni1 O25 88.15(10) . . ?
O2 Ni1 O26 88.97(9) . . ?
N19 Ni1 O26 178.71(11) . . ?
O25 Ni1 O26 92.93(9) . . ?
O2 Ni1 N13 87.24(10) . . ?
N19 Ni1 N13 89.64(12) . . ?
O25 Ni1 N13 177.62(10) . . ?
O26 Ni1 N13 89.30(10) . . ?
O2 Ni1 O27 172.75(10) . . ?
N19 Ni1 O27 94.59(12) . . ?
O25 Ni1 O27 84.68(10) . . ?
O26 Ni1 O27 84.80(10) . . ?
N13 Ni1 O27 96.38(11) . . ?
C3 O2 Ni1 128.5(2) . . ?
O4 C3 O2 125.4(3) . . ?
O4 C3 C5 119.1(3) . . ?
O2 C3 C5 115.3(3) . . ?
C6 C5 C7 120.3(3) . . ?
C6 C5 C3 115.8(3) . . ?
C7 C5 C3 123.4(3) . . ?
C5 C6 C9 120.4(3) . 2_657 ?
C5 C6 H6 119.8 . . ?
C9 C6 H6 119.8 2_657 . ?
C5 C7 C8 122.7(3) . . ?
C5 C7 C7 119.0(4) . 2_657 ?
C8 C7 C7 118.3(4) . 2_657 ?
C9 C8 C7 120.4(3) . . ?
C9 C8 C10 116.8(3) . . ?
C7 C8 C10 122.1(3) . . ?
C8 C9 C6 120.7(3) . 2_657 ?
C8 C9 H9 119.7 . . ?
C6 C9 H9 119.6 2_657 . ?
O12 C10 O11 124.5(3) . . ?
O12 C10 C8 116.7(3) . . ?
O11 C10 C8 118.6(3) . . ?
C14 N13 C18 117.9(3) . . ?
C14 N13 Ni1 121.4(2) . . ?
C18 N13 Ni1 120.6(3) . . ?
N13 C14 C15 122.9(4) . . ?
N13 C14 H14 118.5 . . ?
C15 C14 H14 118.5 . . ?
C16 C15 C14 118.4(4) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C17 C16 C15 119.2(4) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 118.9(4) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
N13 C18 C17 122.8(4) . . ?
N13 C18 H18 118.6 . . ?
C17 C18 H18 118.6 . . ?
C20 N19 C24 117.7(3) . . ?
C20 N19 Ni1 123.3(3) . . ?
C24 N19 Ni1 119.0(2) . . ?
N19 C20 C21 122.1(4) . . ?
N19 C20 H20 119.0 . . ?
C21 C20 H20 119.0 . . ?
C22 C21 C20 119.3(4) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 119.2(4) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C22 C23 C24 118.7(5) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
N19 C24 C23 123.0(4) . . ?
N19 C24 H24 118.5 . . ?
C23 C24 H24 118.5 . . ?
Ni1 O25 H25A 98.7 . . ?
Ni1 O25 H25B 118.5 . . ?
H25A O25 H25B 104.3 . . ?
Ni1 O26 H26A 112.0 . . ?
Ni1 O26 H26B 118.1 . . ?
H26A O26 H26B 98.2 . . ?
Ni1 O27 H27A 130.6 . . ?
Ni1 O27 H27B 115.2 . . ?
H27A O27 H27B 104.0 . . ?
H28A O28 H28B 94.1 . . ?
H29A O29 H29B 105.8 . . ?
H30A O30 H30B 120.6 . . ?
H31A O31 H31B 102.9 . . ?
H32A O32 H32B 100.8 . . ?
N38 C33 C34 124.1(11) . . ?
N38 C33 H33 118.8 . . ?
C34 C33 H33 116.9 . . ?
C35 C34 C33 118.0(10) . . ?
C35 C34 H34 120.8 . . ?
C33 C34 H34 121.2 . . ?
C36 C35 C34 118.2(9) . . ?
C36 C35 H35 122.6 . . ?
C34 C35 H35 119.2 . . ?
C37 C36 C35 120.3(10) . . ?
C37 C36 H36 122.3 . . ?
C35 C36 H36 117.4 . . ?
N38 C37 C36 122.2(9) . . ?
N38 C37 H37 120.1 . . ?
C36 C37 H37 117.7 . . ?
C33 N38 C37 117.1(10) . . ?
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 O2 2.052(2) . ?
Ni1 N19 2.074(3) . ?
Ni1 O25 2.080(2) . ?
Ni1 O26 2.089(2) . ?
Ni1 N13 2.090(3) . ?
Ni1 O27 2.098(3) . ?
O2 C3 1.269(4) . ?
C3 O4 1.260(4) . ?
C3 C5 1.508(4) . ?
C5 C6 1.377(5) . ?
C5 C7 1.428(5) . ?
C6 C9 1.410(5) 2_657 ?
C6 H6 0.9500 . ?
C7 C8 1.432(4) . ?
C7 C7 1.438(6) 2_657 ?
C8 C9 1.375(5) . ?
C8 C10 1.508(4) . ?
C9 C6 1.410(5) 2_657 ?
C9 H9 0.9500 . ?
C10 O12 1.248(4) . ?
C10 O11 1.275(4) . ?
N13 C14 1.336(5) . ?
N13 C18 1.346(5) . ?
C14 C15 1.392(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N19 C20 1.333(5) . ?
N19 C24 1.347(5) . ?
C20 C21 1.403(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.364(8) . ?
C21 H21 0.9500 . ?
C22 C23 1.373(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.383(5) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
O25 H25A 0.9004 . ?
O25 H25B 0.8978 . ?
O26 H26A 0.8979 . ?
O26 H26B 0.8946 . ?
O27 H27A 0.9036 . ?
O27 H27B 0.9015 . ?
O28 H28A 0.8965 . ?
O28 H28B 0.8973 . ?
O29 H29A 0.8980 . ?
O29 H29B 0.8980 . ?
O30 H30A 0.8965 . ?
O30 H30B 0.8962 . ?
O31 H31A 0.8968 . ?
O31 H31B 0.8988 . ?
O32 H32A 0.9014 . ?
O32 H32B 0.8971 . ?
C33 N38 1.336(14) . ?
C33 C34 1.396(15) . ?
C33 H33 1.0383 . ?
C34 C35 1.385(16) . ?
C34 H34 0.9500 . ?
C35 C36 1.383(18) . ?
C35 H35 0.9500 . ?
C36 C37 1.382(17) . ?
C36 H36 0.9500 . ?
C37 N38 1.348(12) . ?
C37 H37 0.9500 . ?
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
O25 H25A O4 0.90 1.77 2.645(3) 164.8 .
O25 H25B O11 0.90 1.84 2.733(3) 174.5 2_667
O26 H26A O12 0.90 1.71 2.586(3) 166.1 2_667
O26 H26B O11 0.89 1.91 2.748(3) 154.7 .
O27 H27A O28 0.90 1.82 2.728(4) 176.9 2_566
O27 H27B O12 0.90 2.57 3.298(4) 138.2 2_667
O28 H28A O26 0.90 1.93 2.824(3) 171.8 1_554
O28 H28B O31 0.90 1.89 2.777(4) 168.0 .
O29 H29A O31 0.90 2.14 2.940(4) 147.3 1_545
O29 H29B O32 0.90 1.89 2.776(4) 167.2 .
O30 H30A O11 0.90 1.86 2.751(4) 172.4 1_554
O30 H30B O28 0.90 2.07 2.857(4) 145.7 .
O31 H31A O4 0.90 1.85 2.746(4) 172.6 2_666
O31 H31B O29 0.90 1.87 2.763(4) 171.9 2_666
O32 H32A O30 0.90 1.91 2.808(4) 172.7 2_666
O32 H32B O30 0.90 2.00 2.815(4) 151.1 .
