#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:22:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180335 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/04/7200444.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_7200444
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         'C12 H15 Co N O8, 5(H2 O), (O H)'
_chemical_formula_sum            'C12 H26 Co N O14'
_chemical_formula_weight         467.27
_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                92.4596(12)
_cell_angle_beta                 110.2511(16)
_cell_angle_gamma                100.3501(9)
_cell_formula_units_Z            2
_cell_length_a                   9.0654(2)
_cell_length_b                   10.6309(3)
_cell_length_c                   11.5309(2)
_cell_measurement_reflns_used    3760
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.12
_cell_measurement_theta_min      2.45
_cell_volume                     1018.94(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      110(2)
_diffrn_detector_area_resol_mean 12.8
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '0.8 deg. φ and ω scan'
_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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11413
_diffrn_reflns_theta_full        28.12
_diffrn_reflns_theta_max         28.12
_diffrn_reflns_theta_min         2.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.911
_exptl_absorpt_correction_T_max  0.8755
_exptl_absorpt_correction_T_min  0.7718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0399
_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)+(0.0524P)²+0.7857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1071
_reflns_number_gt                3968
_reflns_number_total             4841
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b815885a.txt
_cod_data_source_block           Compound8(ra4)
_cod_database_code               7200444
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
Co1 Co 0.81893(3) 0.21629(3) 0.16882(2) 0.01252(10) Uani 1 1 d . . .
O2 O 0.72641(17) 0.13203(14) 0.30253(12) 0.0134(3) Uani 1 1 d . . .
C3 C 0.7429(2) 0.0263(2) 0.34795(17) 0.0126(4) Uani 1 1 d . . .
O4 O 0.81782(18) -0.05128(15) 0.31997(13) 0.0156(3) Uani 1 1 d . . .
C5 C 0.6788(2) 0.0001(2) 0.45135(17) 0.0128(4) Uani 1 1 d . . .
C6 C 0.7939(2) -0.0128(2) 0.56301(18) 0.0138(4) Uani 1 1 d . . .
H6 H 0.8981 -0.0197 0.5658 0.017 Uiso 1 1 calc R . .
C7 C 0.5179(2) 0.00144(19) 0.44401(17) 0.0112(4) Uani 1 1 d . . .
C8 C 0.3906(2) 0.00643(19) 0.32955(17) 0.0117(4) Uani 1 1 d . . .
C9 C 0.2407(3) 0.0159(2) 0.32748(18) 0.0149(4) Uani 1 1 d . . .
H9 H 0.1598 0.0245 0.2513 0.018 Uiso 1 1 calc R . .
C10 C 0.4042(2) -0.0119(2) 0.20357(17) 0.0123(4) Uani 1 1 d . . .
O11 O 0.34709(17) 0.06474(14) 0.12573(12) 0.0142(3) Uani 1 1 d . . .
O12 O 0.46232(18) -0.10415(14) 0.18116(12) 0.0150(3) Uani 1 1 d . . .
N13 N 0.8893(2) 0.28567(17) 0.02043(15) 0.0147(4) Uani 1 1 d . . .
C14 C 0.8177(3) 0.3738(2) -0.0452(2) 0.0187(4) Uani 1 1 d . . .
H14 H 0.7430 0.4087 -0.0196 0.022 Uiso 1 1 calc R . .
C15 C 0.8481(3) 0.4161(2) -0.1484(2) 0.0226(5) Uani 1 1 d . . .
H15 H 0.7949 0.4783 -0.1926 0.027 Uiso 1 1 calc R . .
C16 C 0.9572(3) 0.3660(2) -0.1860(2) 0.0264(5) Uani 1 1 d . . .
H16 H 0.9801 0.3931 -0.2566 0.032 Uiso 1 1 calc R . .
C17 C 1.0326(3) 0.2757(2) -0.1188(2) 0.0279(5) Uani 1 1 d . . .
H17 H 1.1090 0.2406 -0.1420 0.034 Uiso 1 1 calc R . .
C18 C 0.9949(3) 0.2372(2) -0.0169(2) 0.0204(5) Uani 1 1 d . . .
H18 H 1.0455 0.1742 0.0280 0.024 Uiso 1 1 calc R . .
O19 O 0.58236(17) 0.19144(15) 0.04817(13) 0.0154(3) Uani 1 1 d . . .
H19A H 0.5055 0.1422 0.0686 0.023 Uiso 1 1 d R . .
H19B H 0.5591 0.1541 -0.0292 0.023 Uiso 1 1 d R . .
O20 O 0.84966(18) 0.03432(14) 0.11408(13) 0.0144(3) Uani 1 1 d . . .
H20A H 0.7852 -0.0054 0.0386 0.022 Uiso 1 1 d R . .
H20B H 0.8291 -0.0141 0.1710 0.022 Uiso 1 1 d R . .
O21 O 0.79256(19) 0.39542(14) 0.23558(14) 0.0177(3) Uani 1 1 d . . .
H21A H 0.7002 0.4207 0.1980 0.027 Uiso 1 1 d R . .
H21B H 0.8146 0.4047 0.3176 0.027 Uiso 1 1 d R . .
O22 O 1.05364(18) 0.26215(15) 0.29763(13) 0.0185(3) Uani 1 1 d . . .
H22A H 1.0788 0.2561 0.3789 0.028 Uiso 1 1 d R . .
H22B H 1.1449 0.2834 0.2830 0.028 Uiso 1 1 d R . .
O23 O 0.5087(2) 0.47921(15) 0.12580(14) 0.0218(3) Uani 1 1 d . . .
H23A H 0.5218 0.5496 0.1761 0.033 Uiso 1 1 d R . .
O24 O 0.8141(3) 0.3403(2) 0.47759(18) 0.0244(7) Uani 0.814(7) 1 d P . .
H24A H 0.7294 0.3625 0.4893 0.037 Uiso 1 1 d R A .
H24B H 0.7645 0.2658 0.4295 0.037 Uiso 1 1 d R . .
O24' O 0.8675(14) 0.4224(13) 0.5000(10) 0.034(4) Uiso 0.186(7) 1 d P A 1
O25 O 0.4450(2) 0.31385(15) 0.70172(14) 0.0228(4) Uani 1 1 d . . .
H25A H 0.4729 0.2424 0.7337 0.034 Uiso 1 1 d R . .
H25B H 0.3394 0.3039 0.6632 0.034 Uiso 1 1 d R . .
O26 O 0.33893(19) 0.29926(15) 0.24158(14) 0.0207(3) Uani 1 1 d . . .
H26A H 0.3375 0.2224 0.2049 0.031 Uiso 1 1 d R . .
H26B H 0.3877 0.3546 0.2027 0.031 Uiso 1 1 d R . .
O27 O 0.1091(2) 0.26215(17) 0.55242(14) 0.0248(4) Uani 1 1 d . . .
H27A H 0.1161 0.1881 0.5869 0.037 Uiso 1 1 d R . .
H27B H 0.0255 0.2979 0.5496 0.037 Uiso 1 1 d R . .
O28 O 0.5320(2) 0.37730(18) 0.49744(15) 0.0295(4) Uani 1 1 d . . .
H28A H 0.5124 0.3537 0.5648 0.044 Uiso 1 1 d R . .
H28B H 0.4541 0.3497 0.4237 0.044 Uiso 1 1 d R . .
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'
Co Co 0.3494 0.9721 '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
O19 Co1 O22 173.27(6) . . ?
O19 Co1 O20 95.23(6) . . ?
O22 Co1 O20 91.50(6) . . ?
O19 Co1 O21 86.85(6) . . ?
O22 Co1 O21 86.42(6) . . ?
O20 Co1 O21 176.28(5) . . ?
O19 Co1 N13 87.50(6) . . ?
O22 Co1 N13 93.10(6) . . ?
O20 Co1 N13 87.48(6) . . ?
O21 Co1 N13 95.70(6) . . ?
O19 Co1 O2 87.30(6) . . ?
O22 Co1 O2 92.49(6) . . ?
O20 Co1 O2 89.35(6) . . ?
O21 Co1 O2 87.66(6) . . ?
N13 Co1 O2 173.64(6) . . ?
C3 O2 Co1 128.70(13) . . ?
O4 C3 O2 124.99(18) . . ?
O4 C3 C5 118.62(18) . . ?
O2 C3 C5 116.16(18) . . ?
C6 C5 C7 120.09(18) . . ?
C6 C5 C3 114.25(18) . . ?
C7 C5 C3 125.33(17) . . ?
C5 C6 C9 120.95(19) . 2_656 ?
C5 C6 H6 119.5 . . ?
C9 C6 H6 119.5 2_656 . ?
C8 C7 C5 122.83(17) . . ?
C8 C7 C7 118.2(2) . 2_656 ?
C5 C7 C7 119.0(2) . 2_656 ?
C9 C8 C7 121.07(17) . . ?
C9 C8 C10 115.10(17) . . ?
C7 C8 C10 123.53(18) . . ?
C8 C9 C6 120.47(18) . 2_656 ?
C8 C9 H9 119.8 . . ?
C6 C9 H9 119.8 2_656 . ?
O12 C10 O11 125.15(18) . . ?
O12 C10 C8 117.94(17) . . ?
O11 C10 C8 116.80(18) . . ?
C14 N13 C18 117.82(18) . . ?
C14 N13 Co1 119.69(14) . . ?
C18 N13 Co1 122.28(14) . . ?
N13 C14 C15 123.0(2) . . ?
N13 C14 H14 118.5 . . ?
C15 C14 H14 118.5 . . ?
C16 C15 C14 118.8(2) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 118.8(2) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C16 C17 C18 119.1(2) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
N13 C18 C17 122.5(2) . . ?
N13 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
Co1 O19 H19A 118.2 . . ?
Co1 O19 H19B 116.7 . . ?
H19A O19 H19B 99.9 . . ?
Co1 O20 H20A 118.3 . . ?
Co1 O20 H20B 103.0 . . ?
H20A O20 H20B 107.6 . . ?
Co1 O21 H21A 118.2 . . ?
Co1 O21 H21B 113.4 . . ?
H21A O21 H21B 108.3 . . ?
Co1 O22 H22A 123.5 . . ?
Co1 O22 H22B 128.1 . . ?
H22A O22 H22B 108.2 . . ?
O24' O24 H24A 89.5 . . ?
O24' O24 H24B 159.3 . . ?
H24A O24 H24B 98.9 . . ?
O24 O24' H24A 45.1 . . ?
H25A O25 H25B 112.3 . . ?
H26A O26 H26B 102.3 . . ?
H27A O27 H27B 117.6 . . ?
H28A O28 H28B 117.2 . . ?
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
Co1 O19 2.0746(14) . ?
Co1 O22 2.0853(15) . ?
Co1 O20 2.1044(15) . ?
Co1 O21 2.1075(15) . ?
Co1 N13 2.1387(17) . ?
Co1 O2 2.1510(14) . ?
O2 C3 1.272(2) . ?
C3 O4 1.255(3) . ?
C3 C5 1.512(3) . ?
C5 C6 1.379(3) . ?
C5 C7 1.435(3) . ?
C6 C9 1.403(3) 2_656 ?
C6 H6 0.9500 . ?
C7 C8 1.432(3) . ?
C7 C7 1.437(4) 2_656 ?
C8 C9 1.372(3) . ?
C8 C10 1.507(3) . ?
C9 C6 1.403(3) 2_656 ?
C9 H9 0.9500 . ?
C10 O12 1.251(3) . ?
C10 O11 1.276(2) . ?
N13 C14 1.346(3) . ?
N13 C18 1.345(3) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
O19 H19A 0.8989 . ?
O19 H19B 0.8983 . ?
O20 H20A 0.8972 . ?
O20 H20B 0.8993 . ?
O21 H21A 0.8949 . ?
O21 H21B 0.8930 . ?
O22 H22A 0.8922 . ?
O22 H22B 0.8929 . ?
O23 H23A 0.8905 . ?
O24 O24' 0.897(13) . ?
O24 H24A 0.8929 . ?
O24 H24B 0.8934 . ?
O24' H24A 1.2601 . ?
O25 H25A 0.8974 . ?
O25 H25B 0.8891 . ?
O26 H26A 0.8992 . ?
O26 H26B 0.8992 . ?
O27 H27A 0.8999 . ?
O27 H27B 0.8988 . ?
O28 H28A 0.8916 . ?
O28 H28B 0.8925 . ?
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
O19 H19A O11 0.90 1.86 2.749(2) 170.7 .
O19 H19B O12 0.90 1.74 2.6326(19) 170.2 2_655
O20 H20A O11 0.90 1.87 2.7564(19) 171.8 2_655
O20 H20B O4 0.90 1.81 2.667(2) 157.9 .
O21 H21A O23 0.89 1.88 2.772(2) 177.3 .
O21 H21B O24 0.89 2.00 2.824(2) 153.4 .
O22 H22A O27 0.89 1.92 2.804(2) 170.5 1_655
O22 H22B O26 0.89 1.96 2.842(2) 170.4 1_655
O23 H23A O25 0.89 1.89 2.772(2) 173.1 2_666
O24 H24A O28 0.89 1.86 2.739(3) 168.9 .
O24 H24B O2 0.89 1.89 2.735(3) 156.6 .
O25 H25A O12 0.90 1.87 2.765(2) 173.2 2_656
O25 H25B O27 0.89 1.99 2.868(2) 169.4 .
O26 H26A O11 0.90 1.90 2.803(2) 176.2 .
O26 H26B O23 0.90 2.00 2.897(2) 176.4 .
O27 H27A O4 0.90 1.90 2.788(2) 166.5 2_656
O27 H27B O24 0.90 1.95 2.802(3) 157.3 1_455
O28 H28A O25 0.89 1.92 2.803(2) 172.1 .
O28 H28B O26 0.89 1.99 2.855(2) 161.9 .
