#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/95/2019543.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_2019543
loop_
_publ_author_name
'Atria, Ana María'
'Garland, Maria Teresa'
'Baggio, Ricardo'
_publ_section_title
;
 Two nickel(II) bis[(pyridin-2-yl)methyl]amine complexes with homophthalic
 and benzene-1,2,4,5-tetracarboxylic acids
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              541
_journal_page_last               546
_journal_paper_doi               10.1107/S2053229614008134
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          '[Ni (C9 H6 O4) (C12 H13 N3) (H2 O)]'
_chemical_formula_moiety         'C21 H21 N3 Ni O5'
_chemical_formula_sum            'C21 H21 N3 Ni O5'
_chemical_formula_weight         454.12
_chemical_name_systematic
catena-Poly[[aqua{bis[(pyridin-2-yl)methyl]amine-κ³N,N',N''}nickel(II)]-μ-2-(2-carboxylatophenyl)aceteto-κ²O:O']
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 93.081(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.233(3)
_cell_length_b                   10.4511(14)
_cell_length_c                   20.898(3)
_cell_measurement_reflns_used    2835
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.79
_cell_measurement_theta_min      2.24
_cell_volume                     3976.5(10)
_computing_cell_refinement       'SAINT-NT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-NT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_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  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15811
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.80
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    1.015
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS in SAINT-NT; Bruker, 2002)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.373
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.434
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4399
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.434
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.002
_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+2.6787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1252
_reflns_number_gt                3562
_reflns_number_total             4399
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            uk3094sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 2019543--2019544.cif.'
_cod_original_cell_volume        3976.3(9)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2019543
_cod_database_fobs_code          2019543
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Ni Ni1 0.268905(17) 0.54699(3) 0.182666(15) 0.01720(13) Uani d . 1 1
N N11 0.32496(12) 0.5816(2) 0.09987(10) 0.0220(5) Uani d . 1 1
N N21 0.28959(13) 0.7444(2) 0.19247(10) 0.0222(5) Uani d D 1 1
H H21N 0.2611(14) 0.785(3) 0.2153(12) 0.027 Uiso d D 1 1
N N31 0.36272(12) 0.5344(2) 0.24201(10) 0.0205(5) Uani d . 1 1
C C11 0.35626(14) 0.4973(3) 0.06188(13) 0.0245(6) Uani d . 1 1
H H1A 0.3570 0.4098 0.0742 0.029 Uiso calc R 1 1
C C21 0.38752(19) 0.5306(3) 0.00586(15) 0.0391(8) Uani d . 1 1
H H21 0.4081 0.4675 -0.0205 0.047 Uiso calc R 1 1
C C31 0.3881(2) 0.6591(4) -0.01100(16) 0.0495(10) Uani d . 1 1
H H31 0.4104 0.6858 -0.0488 0.059 Uiso calc R 1 1
C C41 0.3559(2) 0.7475(3) 0.02769(14) 0.0430(9) Uani d . 1 1
H H41 0.3549 0.8356 0.0164 0.052 Uiso calc R 1 1
C C51 0.32516(16) 0.7061(3) 0.08312(13) 0.0260(6) Uani d . 1 1
C C61 0.28692(17) 0.7966(3) 0.12672(13) 0.0294(6) Uani d . 1 1
H H61A 0.3113 0.8813 0.1267 0.035 Uiso calc R 1 1
H H61B 0.2352 0.8081 0.1109 0.035 Uiso calc R 1 1
C C71 0.36221(15) 0.7644(3) 0.22740(13) 0.0238(6) Uani d . 1 1
H H71A 0.3986 0.7900 0.1963 0.029 Uiso calc R 1 1
H H71B 0.3579 0.8355 0.2583 0.029 Uiso calc R 1 1
C C81 0.38960(14) 0.6485(3) 0.26261(12) 0.0210(5) Uani d . 1 1
C C91 0.44319(15) 0.6562(3) 0.31322(13) 0.0284(6) Uani d . 1 1
H H91 0.4603 0.7371 0.3285 0.034 Uiso calc R 1 1
C C101 0.47052(16) 0.5456(3) 0.34028(14) 0.0336(7) Uani d . 1 1
H H101 0.5066 0.5490 0.3748 0.040 Uiso calc R 1 1
C C111 0.44528(17) 0.4286(3) 0.31707(14) 0.0323(7) Uani d . 1 1
H H111 0.4652 0.3508 0.3340 0.039 Uiso calc R 1 1
C C121 0.39053(15) 0.4277(3) 0.26882(13) 0.0248(6) Uani d . 1 1
H H121 0.3718 0.3476 0.2540 0.030 Uiso calc R 1 1
O O12 0.10542(10) 0.6298(2) 0.23059(9) 0.0275(4) Uani d . 1 1
O O22 0.21205(10) 0.54161(17) 0.26559(9) 0.0215(4) Uani d . 1 1
O O32 0.23373(10) 0.85118(19) 0.33165(9) 0.0254(4) Uani d . 1 1
O O42 0.33763(11) 0.83428(19) 0.39241(9) 0.0287(4) Uani d . 1 1
C C12 0.12750(14) 0.6080(2) 0.34231(12) 0.0187(5) Uani d . 1 1
C C22 0.05291(15) 0.5936(3) 0.35230(14) 0.0247(6) Uani d . 1 1
H H22 0.0194 0.5791 0.3166 0.030 Uiso calc R 1 1
C C32 0.02663(16) 0.5999(3) 0.41350(14) 0.0310(7) Uani d . 1 1
H H32 -0.0242 0.5889 0.4197 0.037 Uiso calc R 1 1
C C42 0.07535(17) 0.6224(3) 0.46512(14) 0.0308(7) Uani d . 1 1
H H42 0.0583 0.6260 0.5072 0.037 Uiso calc R 1 1
C C52 0.14927(16) 0.6398(3) 0.45535(13) 0.0271(6) Uani d . 1 1
H H52 0.1820 0.6574 0.4912 0.033 Uiso calc R 1 1
C C62 0.17708(14) 0.6323(2) 0.39446(12) 0.0188(5) Uani d . 1 1
C C72 0.15014(14) 0.5928(2) 0.27372(12) 0.0202(5) Uani d . 1 1
C C82 0.25815(15) 0.6559(2) 0.38849(12) 0.0215(5) Uani d . 1 1
H H82A 0.2762 0.5963 0.3561 0.026 Uiso calc R 1 1
H H82B 0.2842 0.6354 0.4300 0.026 Uiso calc R 1 1
C C92 0.27836(14) 0.7920(2) 0.36970(11) 0.0176(5) Uani d . 1 1
O O1W 0.17249(11) 0.58304(19) 0.12623(9) 0.0250(4) Uani d D 1 1
H H1WA 0.1641(16) 0.5069(14) 0.1137(14) 0.030 Uiso d D 1 1
H H1WB 0.1416(13) 0.598(3) 0.1542(11) 0.030 Uiso d D 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N31 Ni1 O22 . . 86.06(8)
N31 Ni1 O32 . 4_545 92.06(8)
O22 Ni1 O32 . 4_545 94.91(7)
N31 Ni1 N11 . . 94.72(9)
O22 Ni1 N11 . . 171.57(8)
O32 Ni1 N11 4_545 . 93.45(8)
N31 Ni1 O1W . . 172.97(8)
O22 Ni1 O1W . . 91.91(7)
O32 Ni1 O1W 4_545 . 94.83(7)
N11 Ni1 O1W . . 86.32(8)
N31 Ni1 N21 . . 82.28(9)
O22 Ni1 N21 . . 92.31(8)
O32 Ni1 N21 4_545 . 170.50(8)
N11 Ni1 N21 . . 79.50(9)
O1W Ni1 N21 . . 91.09(9)
C11 N11 C51 . . 118.4(2)
C11 N11 Ni1 . . 128.51(19)
C51 N11 Ni1 . . 113.01(18)
C61 N21 C71 . . 112.8(2)
C61 N21 Ni1 . . 105.95(16)
C71 N21 Ni1 . . 109.55(16)
C61 N21 H21N . . 110(2)
C71 N21 H21N . . 102(2)
Ni1 N21 H21N . . 116(2)
C121 N31 C81 . . 118.7(2)
C121 N31 Ni1 . . 126.13(19)
C81 N31 Ni1 . . 114.23(17)
N11 C11 C21 . . 123.4(3)
N11 C11 H1A . . 118.3
C21 C11 H1A . . 118.3
C11 C21 C31 . . 118.0(3)
C11 C21 H21 . . 121.0
C31 C21 H21 . . 121.0
C41 C31 C21 . . 119.3(3)
C41 C31 H31 . . 120.3
C21 C31 H31 . . 120.3
C31 C41 C51 . . 119.1(3)
C31 C41 H41 . . 120.5
C51 C41 H41 . . 120.5
N11 C51 C41 . . 121.8(3)
N11 C51 C61 . . 116.1(2)
C41 C51 C61 . . 122.0(3)
N21 C61 C51 . . 109.7(2)
N21 C61 H61A . . 109.7
C51 C61 H61A . . 109.7
N21 C61 H61B . . 109.7
C51 C61 H61B . . 109.7
H61A C61 H61B . . 108.2
C81 C71 N21 . . 113.1(2)
C81 C71 H71A . . 109.0
N21 C71 H71A . . 109.0
C81 C71 H71B . . 109.0
N21 C71 H71B . . 109.0
H71A C71 H71B . . 107.8
N31 C81 C91 . . 121.1(3)
N31 C81 C71 . . 117.0(2)
C91 C81 C71 . . 121.8(3)
C101 C91 C81 . . 119.1(3)
C101 C91 H91 . . 120.5
C81 C91 H91 . . 120.5
C91 C101 C111 . . 119.6(3)
C91 C101 H101 . . 120.2
C111 C101 H101 . . 120.2
C121 C111 C101 . . 118.4(3)
C121 C111 H111 . . 120.8
C101 C111 H111 . . 120.8
N31 C121 C111 . . 123.0(3)
N31 C121 H121 . . 118.5
C111 C121 H121 . . 118.5
C72 O22 Ni1 . . 126.19(17)
C92 O32 Ni1 . 4 125.65(17)
C22 C12 C62 . . 119.8(2)
C22 C12 C72 . . 116.5(2)
C62 C12 C72 . . 123.7(2)
C32 C22 C12 . . 121.3(3)
C32 C22 H22 . . 119.4
C12 C22 H22 . . 119.4
C42 C32 C22 . . 119.2(3)
C42 C32 H32 . . 120.4
C22 C32 H32 . . 120.4
C32 C42 C52 . . 119.8(3)
C32 C42 H42 . . 120.1
C52 C42 H42 . . 120.1
C42 C52 C62 . . 122.0(3)
C42 C52 H52 . . 119.0
C62 C52 H52 . . 119.0
C52 C62 C12 . . 117.9(2)
C52 C62 C82 . . 118.1(2)
C12 C62 C82 . . 124.0(2)
O12 C72 O22 . . 126.0(2)
O12 C72 C12 . . 116.7(2)
O22 C72 C12 . . 117.3(2)
C62 C82 C92 . . 115.1(2)
C62 C82 H82A . . 108.5
C92 C82 H82A . . 108.5
C62 C82 H82B . . 108.5
C92 C82 H82B . . 108.5
H82A C82 H82B . . 107.5
O42 C92 O32 . . 125.7(2)
O42 C92 C82 . . 116.9(2)
O32 C92 C82 . . 117.4(2)
Ni1 O1W H1WA . . 98(2)
Ni1 O1W H1WB . . 102(2)
H1WA O1W H1WB . . 105.7(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 N31 . 2.062(2) y
Ni1 O22 . 2.0674(18) y
Ni1 O32 4_545 2.068(2) y
Ni1 N11 . 2.088(2) y
Ni1 O1W . 2.098(2) y
Ni1 N21 . 2.106(2) y
N11 C11 . 1.334(4) ?
N11 C51 . 1.347(4) ?
N21 C61 . 1.477(3) ?
N21 C71 . 1.492(4) ?
N21 H21N . 0.841(10) ?
N31 C121 . 1.335(3) ?
N31 C81 . 1.351(3) ?
C11 C21 . 1.374(4) ?
C11 H1A . 0.9500 ?
C21 C31 . 1.388(5) ?
C21 H21 . 0.9500 ?
C31 C41 . 1.379(5) ?
C31 H31 . 0.9500 ?
C41 C51 . 1.383(4) ?
C41 H41 . 0.9500 ?
C51 C61 . 1.510(4) ?
C61 H61A . 0.9900 ?
C61 H61B . 0.9900 ?
C71 C81 . 1.490(4) ?
C71 H71A . 0.9900 ?
C71 H71B . 0.9900 ?
C81 C91 . 1.403(4) ?
C91 C101 . 1.369(4) ?
C91 H91 . 0.9500 ?
C101 C111 . 1.385(5) ?
C101 H101 . 0.9500 ?
C111 C121 . 1.380(4) ?
C111 H111 . 0.9500 ?
C121 H121 . 0.9500 ?
O12 C72 . 1.244(3) ?
O22 C72 . 1.269(3) ?
O32 C92 . 1.268(3) ?
O42 C92 . 1.238(3) ?
C12 C22 . 1.395(4) ?
C12 C62 . 1.401(4) ?
C12 C72 . 1.521(3) ?
C22 C32 . 1.391(4) ?
C22 H22 . 0.9500 ?
C32 C42 . 1.380(4) ?
C32 H32 . 0.9500 ?
C42 C52 . 1.386(4) ?
C42 H42 . 0.9500 ?
C52 C62 . 1.397(4) ?
C52 H52 . 0.9500 ?
C62 C82 . 1.510(4) ?
C82 C92 . 1.525(4) ?
C82 H82A . 0.9900 ?
C82 H82B . 0.9900 ?
O1W H1WA . 0.849(10) ?
O1W H1WB . 0.848(10) ?
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
O1W H1WB O12 . 0.84(2) 1.79(2) 2.603(3) 162(2)
C82 H82A O22 . 0.99 2.24 2.916(3) 124
C121 H121 O32 4_545 0.95 2.55 3.110(4) 118
O1W H1WA O42 4_545 0.84(2) 1.814(15) 2.632(3) 163(3)
C71 H71B O22 4_555 0.99 2.54 3.205(4) 125
C121 H121 O12 4_545 0.95 2.33 3.114(4) 139
C22 H22 O12 2_555 0.95 2.49 3.309(3) 144
C52 H52 O42 7_566 0.95 2.48 3.191(3) 131
