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Acta Cryst. (2008). E64, m1431    [ doi:10.1107/S160053680803314X ]

catena-Poly[[(1,12,15,26-tetraaza-5,8,19,22-tetraoxa-3,4:9,10:17,18:23,24-tetrabenzocyclooctacosane-[kappa]4N1,N12,N15,N26)nickel(II)]-[mu]-terephthalato-[kappa]2O1:O4]

S.-M. Meng, Y.-Q. Fan and Y. Guo

Abstract top

In the title compound, [Ni(C8H4O4)(C36H44N4O4)]n, the NiII atom is coordinated in a distorted octahedral geometry by the four N atoms of the 1,12,15,26-tetraaza-5,8,19,22-tetra-oxa-3,4:9,10:17,18:23,24-tetrabenzocyclooctacosane ligand and two O atoms from the terephthalate dianions. The NiII atoms, which lie on inversion centres, are linked via terephthalate ligands to form a chain structure along [101]. The structure is stabilized by three intramolecular and one intermolecular N-H...O hydrogen bonds.

Comment top

In recent years, intense research activity has been directed toward the assembly of carboxylato-bridged macrocyclic polymers due to their intriguing multidimensional networks (Choi & Suh, 1999; Massoud et al. 2006; Ray et al. 2006). As an extension of the research on the macrocyclic complexes, we have prepared the title compound, (I). In this paper the crystal structure of (I) is reportd.

In the title compound, the NiII atom, which lies on an inversion centre, displays a distorted octahedral coordination geometry provided by four nitrogen atoms from the ligand, 3,4:9,10:17,18:23,24-tetrabenzo- 1,12,15,26-tetraaza-5,8,19,22-tetraoxacyclooctacosane (L) and two oxygen atoms from two distinct terephthalate (tp) dianion ligands (Fig. 1). The bond distances and angles show normal values (Jiang et al. 2005). The NiII atoms are linked via tp ligands to form a one-dimensional chain structure (Fig. 2). The constituent of the title compound are linked through hydrogen bonds to form a complicated three-dimensional network (Table 1); the N and C atoms play a role as donors, while carboxylate-O atoms function as acceptors in these hydrogen bonds.

Related literature top

For general background, see: Choi & Suh (1999); Massoud et al. (2006); Ray et al. (2006). For a related structure, see: Jiang et al. (2005). Please check added text.

Experimental top

A mixture of NiCO3 (0.119 mg, 1 mmol), terephthalic acid (0.162 mg, 1 mmol) and 3,4:9,10:17,18:23,24-tetrabenzo-1,12,15,26-tetraaza-5,8,19,22 -tetraoxacyclooctacosane (0.596 mg, 1 mmol) in EtOH (10 ml) was placed in a Teflon reactor and heated at 393 K for 3 days, and then it was gradually cooled to room temperature at a rate of 10 K.h-1. Green crystals were obtained.

Refinement top

All H atoms bound to C atoms were positioned geometrically and refined as riding, with C—H = 0.93 Å (CH) and 0.97 Å (CH2) and Uiso(H) = 1.2Ueq(C). The H atoms bound to N atoms were located in a difference Fourier map and refined with Uiso(H) = 1.2Ueq(N).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level and H atoms have been omitted for clarity. [Symmetry code: (i) x + 1/2, 1/2 - y, 1/2 + z]
[Figure 2] Fig. 2. View of the one-dimensional polymeric chain of the title compound in the unit cell; H atoms have been omitted for clarity.
catena-Poly[[(1,12,15,26-tetraaza-5,8,19,22-tetraoxa-3,4:9,10:17,18:23,24- tetrabenzocyclooctacosane- κ4N1,N12,N15,N26)nickel(II)]- µ-terephthalato-κ2O1:O4] top
Crystal data top
[Ni(C8H4O4)(C36H44N4O4)]F(000) = 1728
Mr = 819.57Dx = 1.357 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9133 reflections
a = 11.407 (3) Åθ = 3.1–27.5°
b = 16.575 (3) ŵ = 0.54 mm−1
c = 21.675 (6) ÅT = 293 K
β = 101.758 (10)°Block, green
V = 4012.2 (17) Å30.35 × 0.28 × 0.21 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer		9133 independent reflections
Radiation source: fine-focus sealed tube5535 reflections with I > 2σ(I)
graphiteRint = 0.095
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = −14→14
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −21→21
Tmin = 0.839, Tmax = 0.910l = −27→28
37289 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0632P)2 + 2.1456P]
where P = (Fo2 + 2Fc2)/3
9133 reflections(Δ/σ)max = 0.001
514 parametersΔρmax = 0.92 e Å−3
4 restraintsΔρmin = −0.79 e Å−3
Crystal data top
[Ni(C8H4O4)(C36H44N4O4)]V = 4012.2 (17) Å3
Mr = 819.57Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.407 (3) ŵ = 0.54 mm−1
b = 16.575 (3) ÅT = 293 K
c = 21.675 (6) Å0.35 × 0.28 × 0.21 mm
β = 101.758 (10)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		9133 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		5535 reflections with I > 2σ(I)
Tmin = 0.839, Tmax = 0.910Rint = 0.095
37289 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.063H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.155Δρmax = 0.92 e Å−3
S = 1.05Δρmin = −0.79 e Å−3
9133 reflectionsAbsolute structure: ?
514 parametersFlack parameter: ?
4 restraintsRogers parameter: ?
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.76937 (4)0.21301 (2)0.898586 (19)0.02536 (13)
C10.5251 (3)0.0013 (2)0.84876 (18)0.0422 (9)
C20.5463 (4)−0.0627 (3)0.8114 (2)0.0660 (14)
H20.6008−0.05650.78520.079*
C30.4876 (5)−0.1363 (3)0.8124 (3)0.0747 (16)
H30.5032−0.17860.78710.090*
C40.4075 (4)−0.1459 (3)0.8502 (2)0.0628 (13)
H40.3674−0.19470.85050.075*
C50.3859 (4)−0.0837 (3)0.8880 (2)0.0573 (12)
H50.3307−0.09020.91380.069*
C60.4457 (4)−0.0118 (2)0.8878 (2)0.0479 (10)
C90.3299 (4)0.0644 (3)0.9479 (2)0.0519 (11)
H9A0.30910.01690.96960.062*
H9B0.26680.07340.91120.062*
C100.3383 (4)0.1346 (3)0.9901 (2)0.0623 (13)
H10A0.25830.15260.99200.075*
H10B0.37790.11851.03220.075*
C110.4113 (3)0.2674 (2)1.00719 (17)0.0414 (9)
C120.3125 (4)0.3033 (3)1.0236 (2)0.0643 (13)
H120.23670.28091.01060.077*
C130.3278 (5)0.3727 (4)1.0595 (3)0.0872 (18)
H130.26210.39771.07060.105*
C140.4397 (6)0.4046 (4)1.0786 (3)0.0852 (18)
H140.45000.45061.10370.102*
C150.5377 (5)0.3695 (3)1.0612 (2)0.0641 (13)
H150.61310.39231.07420.077*
C160.5245 (3)0.3001 (2)1.02442 (17)0.0395 (9)
C170.6303 (3)0.2610 (2)1.00410 (16)0.0389 (9)
H17A0.70250.27581.03400.047*
H17B0.62160.20291.00620.047*
C180.6834 (4)0.3678 (2)0.93574 (19)0.0457 (10)
H18A0.64990.40070.96490.055*
H18B0.65410.38820.89350.055*
C190.8183 (4)0.3724 (2)0.95182 (19)0.0476 (10)
H19A0.84400.42810.95090.057*
H19B0.84790.35120.99380.057*
C200.8686 (4)0.3707 (2)0.84692 (18)0.0435 (9)
H20A0.78750.38710.82820.052*
H20B0.89620.33540.81710.052*
C210.9472 (4)0.4448 (2)0.85675 (18)0.0429 (9)
C220.8995 (5)0.5222 (2)0.8504 (2)0.0600 (12)
H220.81690.52960.84060.072*
C230.9760 (6)0.5892 (3)0.8586 (3)0.0780 (17)
H230.94420.64100.85490.094*
C241.0953 (6)0.5787 (3)0.8720 (3)0.0761 (16)
H241.14520.62360.87680.091*
C251.1447 (5)0.5027 (3)0.8786 (2)0.0646 (13)
H251.22740.49610.88830.077*
C261.0705 (4)0.4364 (2)0.8707 (2)0.0487 (10)
C271.2162 (4)0.3402 (3)0.8544 (3)0.0679 (14)
H27A1.28570.35720.88530.081*
H27B1.21600.36940.81560.081*
C281.2233 (4)0.2533 (3)0.8431 (3)0.0801 (17)
H28A1.29440.24200.82650.096*
H28B1.23050.22470.88270.096*
C291.1211 (4)0.1467 (2)0.78328 (19)0.0444 (9)
C301.2200 (4)0.1073 (3)0.7688 (2)0.0617 (13)
H301.29320.13360.77330.074*
C311.2076 (5)0.0288 (3)0.7478 (2)0.0674 (14)
H311.27380.00160.73930.081*
C321.0996 (5)−0.0101 (3)0.7394 (2)0.0665 (13)
H321.0920−0.06280.72430.080*
C331.0018 (4)0.0298 (3)0.7534 (2)0.0561 (11)
H330.92810.00380.74700.067*
C341.0114 (4)0.1088 (2)0.77716 (18)0.0423 (9)
C350.9067 (3)0.1515 (2)0.79519 (17)0.0388 (9)
H35A0.91450.20890.78830.047*
H35B0.83380.13340.76740.047*
C360.8639 (4)0.0525 (3)0.8715 (3)0.0643 (9)
H36A0.83050.02840.83100.077*
H36B0.93740.02390.88900.077*
C370.7792 (4)0.0404 (3)0.9134 (3)0.0643 (9)
H37A0.7457−0.01350.90750.077*
H37B0.82110.04530.95690.077*
C380.5845 (4)0.0823 (2)0.84676 (19)0.0474 (10)
H38A0.61530.08550.80830.057*
H38B0.52430.12400.84490.057*
C390.5795 (3)0.2704 (2)0.78663 (15)0.0322 (8)
C400.5548 (3)0.2906 (2)0.71679 (15)0.0295 (7)
C410.4375 (3)0.2997 (2)0.68456 (16)0.0364 (8)
H410.37550.29890.70660.044*
C420.4119 (3)0.3100 (2)0.61992 (16)0.0350 (8)
H420.33260.31540.59900.042*
C430.5016 (3)0.3125 (2)0.58600 (15)0.0293 (7)
C440.4709 (3)0.3139 (2)0.51426 (16)0.0335 (8)
C450.6199 (3)0.3074 (2)0.61860 (16)0.0371 (9)
H450.68200.31170.59690.044*
C460.6456 (3)0.2961 (2)0.68337 (16)0.0360 (8)
H460.72490.29210.70460.043*
O10.4368 (3)0.05093 (19)0.92886 (16)0.0669 (7)
O20.4008 (3)0.19793 (19)0.97062 (16)0.0669 (7)
O31.1119 (3)0.35817 (18)0.87622 (17)0.0655 (9)
O41.1251 (3)0.22632 (19)0.80180 (18)0.0706 (10)
O50.4986 (2)0.2814 (2)0.81597 (12)0.0555 (8)
O60.6840 (2)0.24327 (14)0.80900 (10)0.0333 (6)
O70.3600 (2)0.31285 (15)0.49024 (10)0.0349 (6)
O80.5516 (2)0.3137 (2)0.48444 (13)0.0710 (10)
N10.6832 (3)0.09923 (18)0.90061 (15)0.0374 (7)
H1N0.653 (3)0.100 (2)0.9325 (13)0.045*
N20.8942 (3)0.13883 (19)0.86124 (13)0.0343 (7)
H2N0.954 (2)0.153 (2)0.8863 (15)0.041*
N30.8662 (3)0.32447 (18)0.90502 (14)0.0353 (7)
H3N0.9388 (19)0.317 (2)0.9209 (17)0.042*
N40.6460 (2)0.28272 (18)0.93980 (13)0.0327 (6)
H4N0.582 (2)0.275 (2)0.9139 (15)0.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0219 (2)0.0338 (2)0.0203 (2)−0.00261 (19)0.00421 (14)0.00109 (18)
C10.041 (2)0.044 (2)0.038 (2)−0.0139 (18)0.0019 (17)0.0005 (17)
C20.071 (3)0.079 (3)0.053 (3)−0.038 (3)0.025 (2)−0.024 (2)
C30.086 (4)0.068 (3)0.074 (4)−0.034 (3)0.024 (3)−0.037 (3)
C40.067 (3)0.050 (3)0.069 (3)−0.027 (2)0.008 (3)−0.007 (2)
C50.052 (3)0.058 (3)0.061 (3)−0.022 (2)0.011 (2)0.000 (2)
C60.041 (2)0.048 (2)0.055 (3)−0.0132 (19)0.0094 (19)−0.007 (2)
C90.037 (2)0.062 (3)0.060 (3)−0.013 (2)0.017 (2)0.003 (2)
C100.058 (3)0.063 (3)0.076 (3)−0.007 (2)0.037 (3)−0.001 (3)
C110.041 (2)0.055 (2)0.032 (2)−0.0009 (19)0.0169 (16)−0.0058 (17)
C120.042 (2)0.092 (4)0.066 (3)0.002 (2)0.028 (2)−0.016 (3)
C130.080 (4)0.093 (4)0.105 (5)0.010 (3)0.058 (4)−0.029 (4)
C140.098 (5)0.088 (4)0.083 (4)−0.008 (3)0.051 (4)−0.038 (3)
C150.065 (3)0.073 (3)0.062 (3)−0.015 (3)0.029 (2)−0.024 (3)
C160.039 (2)0.054 (2)0.0284 (18)−0.0033 (18)0.0130 (15)−0.0051 (17)
C170.0337 (19)0.057 (2)0.0275 (19)0.0029 (18)0.0086 (15)0.0014 (16)
C180.060 (3)0.038 (2)0.045 (2)0.003 (2)0.024 (2)−0.0016 (18)
C190.062 (3)0.043 (2)0.042 (2)−0.013 (2)0.022 (2)−0.0072 (18)
C200.055 (2)0.046 (2)0.034 (2)−0.008 (2)0.0196 (18)0.0013 (17)
C210.059 (3)0.037 (2)0.037 (2)−0.0095 (19)0.0198 (19)−0.0019 (16)
C220.076 (3)0.041 (2)0.072 (3)0.001 (2)0.036 (3)0.001 (2)
C230.110 (5)0.034 (2)0.104 (5)0.000 (3)0.054 (4)−0.002 (3)
C240.093 (4)0.049 (3)0.095 (4)−0.024 (3)0.041 (3)−0.011 (3)
C250.064 (3)0.056 (3)0.079 (3)−0.023 (2)0.028 (3)−0.009 (2)
C260.060 (3)0.038 (2)0.053 (3)−0.012 (2)0.022 (2)0.0032 (18)
C270.041 (3)0.061 (3)0.103 (4)−0.012 (2)0.017 (3)0.005 (3)
C280.041 (3)0.078 (4)0.112 (5)0.004 (3)−0.007 (3)−0.016 (3)
C290.043 (2)0.047 (2)0.044 (2)0.0136 (19)0.0114 (18)0.0012 (18)
C300.046 (3)0.079 (3)0.064 (3)0.017 (2)0.020 (2)0.008 (3)
C310.071 (3)0.079 (3)0.059 (3)0.035 (3)0.029 (3)0.000 (3)
C320.079 (4)0.061 (3)0.068 (3)0.018 (3)0.034 (3)−0.007 (2)
C330.065 (3)0.052 (2)0.057 (3)0.007 (2)0.026 (2)−0.004 (2)
C340.047 (2)0.046 (2)0.038 (2)0.0129 (19)0.0186 (18)0.0065 (17)
C350.040 (2)0.045 (2)0.034 (2)0.0050 (17)0.0133 (16)0.0007 (16)
C360.068 (2)0.0466 (17)0.085 (3)0.0102 (17)0.0316 (19)0.0148 (17)
C370.068 (2)0.0466 (17)0.085 (3)0.0102 (17)0.0316 (19)0.0148 (17)
C380.045 (2)0.052 (2)0.041 (2)−0.020 (2)0.0005 (18)0.0051 (18)
C390.0295 (18)0.042 (2)0.0235 (17)0.0001 (16)0.0031 (14)0.0026 (14)
C400.0281 (16)0.0335 (17)0.0256 (16)0.0029 (16)0.0026 (13)−0.0014 (14)
C410.0271 (17)0.057 (2)0.0259 (18)0.0063 (17)0.0065 (14)−0.0033 (16)
C420.0227 (16)0.053 (2)0.0271 (18)0.0100 (16)−0.0004 (14)−0.0020 (16)
C430.0266 (17)0.0344 (17)0.0252 (17)0.0023 (15)0.0013 (13)0.0025 (14)
C440.0266 (18)0.049 (2)0.0247 (18)0.0046 (16)0.0034 (14)0.0023 (15)
C450.0240 (17)0.059 (2)0.0280 (18)−0.0045 (17)0.0051 (14)0.0066 (16)
C460.0234 (16)0.051 (2)0.0304 (18)−0.0007 (16)−0.0030 (14)0.0055 (16)
O10.0562 (14)0.0712 (15)0.0840 (17)−0.0255 (12)0.0396 (12)−0.0315 (13)
O20.0562 (14)0.0712 (15)0.0840 (17)−0.0255 (12)0.0396 (12)−0.0315 (13)
O30.059 (2)0.0482 (17)0.096 (3)−0.0060 (16)0.0329 (18)0.0088 (17)
O40.0445 (18)0.061 (2)0.099 (3)0.0058 (16)−0.0041 (17)−0.0072 (18)
O50.0341 (14)0.103 (2)0.0301 (14)0.0175 (16)0.0081 (11)0.0096 (15)
O60.0264 (12)0.0468 (14)0.0250 (12)0.0031 (11)0.0017 (10)0.0051 (10)
O70.0254 (12)0.0561 (15)0.0222 (12)0.0011 (11)0.0022 (9)−0.0025 (11)
O80.0278 (14)0.157 (3)0.0285 (15)0.0042 (18)0.0065 (12)0.0067 (18)
N10.0338 (17)0.0397 (17)0.0370 (18)−0.0087 (14)0.0029 (14)0.0030 (14)
N20.0317 (16)0.0443 (17)0.0275 (16)0.0010 (15)0.0077 (12)0.0011 (13)
N30.0359 (17)0.0403 (16)0.0317 (17)−0.0076 (15)0.0119 (13)−0.0028 (13)
N40.0274 (15)0.0459 (17)0.0261 (15)0.0005 (15)0.0084 (11)0.0014 (14)
Geometric parameters (Å, °) top
Ni1—O62.049 (2)C24—H240.9300
Ni1—O7i2.089 (2)C25—C261.376 (6)
Ni1—N12.131 (3)C25—H250.9300
Ni1—N32.142 (3)C26—O31.377 (5)
Ni1—N42.151 (3)C27—O31.399 (5)
Ni1—N22.160 (3)C27—C281.465 (7)
C1—C61.377 (6)C27—H27A0.9700
C1—C21.384 (6)C27—H27B0.9700
C1—C381.508 (5)C28—O41.359 (5)
C2—C31.393 (6)C28—H28A0.9700
C2—H20.9300C28—H28B0.9700
C3—C41.356 (7)C29—O41.377 (5)
C3—H30.9300C29—C341.382 (6)
C4—C51.370 (6)C29—C301.394 (6)
C4—H40.9300C30—C311.376 (7)
C5—C61.374 (5)C30—H300.9300
C5—H50.9300C31—C321.369 (7)
C6—O11.385 (5)C31—H310.9300
C9—O11.383 (5)C32—C331.383 (6)
C9—C101.471 (6)C32—H320.9300
C9—H9A0.9700C33—C341.402 (6)
C9—H9B0.9700C33—H330.9300
C10—O21.382 (5)C34—C351.506 (5)
C10—H10A0.9700C35—N21.482 (4)
C10—H10B0.9700C35—H35A0.9700
C11—C161.381 (5)C35—H35B0.9700
C11—C121.383 (6)C36—C371.469 (6)
C11—O21.389 (5)C36—N21.500 (5)
C12—C131.380 (7)C36—H36A0.9700
C12—H120.9300C36—H36B0.9700
C13—C141.366 (8)C37—N11.450 (5)
C13—H130.9300C37—H37A0.9700
C14—C151.380 (7)C37—H37B0.9700
C14—H140.9300C38—N11.474 (5)
C15—C161.389 (6)C38—H38A0.9700
C15—H150.9300C38—H38B0.9700
C16—C171.512 (5)C39—O51.236 (4)
C17—N41.485 (4)C39—O61.274 (4)
C17—H17A0.9700C39—C401.519 (4)
C17—H17B0.9700C40—C461.382 (5)
C18—N41.481 (5)C40—C411.386 (4)
C18—C191.508 (6)C41—C421.382 (5)
C18—H18A0.9700C41—H410.9300
C18—H18B0.9700C42—C431.377 (5)
C19—N31.478 (5)C42—H420.9300
C19—H19A0.9700C43—C451.393 (4)
C19—H19B0.9700C43—C441.523 (5)
C20—N31.479 (5)C44—O81.228 (4)
C20—C211.510 (5)C44—O71.267 (4)
C20—H20A0.9700C45—C461.387 (5)
C20—H20B0.9700C45—H450.9300
C21—C261.384 (6)C46—H460.9300
C21—C221.390 (6)O7—Ni1ii2.089 (2)
C22—C231.401 (7)N1—H1N0.83 (2)
C22—H220.9300N2—H2N0.81 (2)
C23—C241.343 (7)N3—H3N0.84 (2)
C23—H230.9300N4—H4N0.83 (2)
C24—C251.376 (7)
O6—Ni1—O7i177.49 (10)C28—C27—H27A109.6
O6—Ni1—N195.97 (11)O3—C27—H27B109.6
O7i—Ni1—N186.54 (11)C28—C27—H27B109.6
O6—Ni1—N389.42 (11)H27A—C27—H27B108.1
O7i—Ni1—N388.08 (11)O4—C28—C27111.5 (4)
N1—Ni1—N3174.59 (12)O4—C28—H28A109.3
O6—Ni1—N492.13 (10)C27—C28—H28A109.3
O7i—Ni1—N487.37 (10)O4—C28—H28B109.3
N1—Ni1—N497.09 (12)C27—C28—H28B109.3
N3—Ni1—N483.23 (12)H28A—C28—H28B108.0
O6—Ni1—N290.38 (10)O4—C29—C34116.1 (3)
O7i—Ni1—N290.20 (10)O4—C29—C30122.3 (4)
N1—Ni1—N281.13 (12)C34—C29—C30121.5 (4)
N3—Ni1—N298.32 (12)C31—C30—C29119.0 (5)
N4—Ni1—N2177.07 (11)C31—C30—H30120.5
C6—C1—C2117.0 (4)C29—C30—H30120.5
C6—C1—C38120.8 (4)C32—C31—C30121.2 (4)
C2—C1—C38122.2 (4)C32—C31—H31119.4
C1—C2—C3121.4 (4)C30—C31—H31119.4
C1—C2—H2119.3C31—C32—C33119.3 (5)
C3—C2—H2119.3C31—C32—H32120.4
C4—C3—C2119.8 (5)C33—C32—H32120.4
C4—C3—H3120.1C32—C33—C34121.4 (5)
C2—C3—H3120.1C32—C33—H33119.3
C3—C4—C5119.9 (4)C34—C33—H33119.3
C3—C4—H4120.1C29—C34—C33117.5 (4)
C5—C4—H4120.1C29—C34—C35120.7 (4)
C4—C5—C6120.1 (5)C33—C34—C35121.8 (4)
C4—C5—H5119.9N2—C35—C34115.0 (3)
C6—C5—H5119.9N2—C35—H35A108.5
C5—C6—C1121.8 (4)C34—C35—H35A108.5
C5—C6—O1123.3 (4)N2—C35—H35B108.5
C1—C6—O1114.9 (3)C34—C35—H35B108.5
O1—C9—C10111.3 (3)H35A—C35—H35B107.5
O1—C9—H9A109.4C37—C36—N2115.0 (4)
C10—C9—H9A109.4C37—C36—H36A108.5
O1—C9—H9B109.4N2—C36—H36A108.5
C10—C9—H9B109.4C37—C36—H36B108.5
H9A—C9—H9B108.0N2—C36—H36B108.5
O2—C10—C9112.6 (4)H36A—C36—H36B107.5
O2—C10—H10A109.1N1—C37—C36110.8 (4)
C9—C10—H10A109.1N1—C37—H37A109.5
O2—C10—H10B109.1C36—C37—H37A109.5
C9—C10—H10B109.1N1—C37—H37B109.5
H10A—C10—H10B107.8C36—C37—H37B109.5
C16—C11—C12121.8 (4)H37A—C37—H37B108.1
C16—C11—O2116.6 (3)N1—C38—C1115.0 (3)
C12—C11—O2121.6 (4)N1—C38—H38A108.5
C13—C12—C11119.2 (5)C1—C38—H38A108.5
C13—C12—H12120.4N1—C38—H38B108.5
C11—C12—H12120.4C1—C38—H38B108.5
C14—C13—C12119.8 (5)H38A—C38—H38B107.5
C14—C13—H13120.1O5—C39—O6126.5 (3)
C12—C13—H13120.1O5—C39—C40118.3 (3)
C13—C14—C15120.8 (5)O6—C39—C40115.2 (3)
C13—C14—H14119.6C46—C40—C41118.6 (3)
C15—C14—H14119.6C46—C40—C39122.0 (3)
C14—C15—C16120.5 (5)C41—C40—C39119.3 (3)
C14—C15—H15119.8C42—C41—C40120.5 (3)
C16—C15—H15119.8C42—C41—H41119.8
C11—C16—C15117.8 (4)C40—C41—H41119.8
C11—C16—C17120.7 (3)C43—C42—C41121.2 (3)
C15—C16—C17121.5 (4)C43—C42—H42119.4
N4—C17—C16115.2 (3)C41—C42—H42119.4
N4—C17—H17A108.5C42—C43—C45118.5 (3)
C16—C17—H17A108.5C42—C43—C44120.3 (3)
N4—C17—H17B108.5C45—C43—C44121.1 (3)
C16—C17—H17B108.5O8—C44—O7125.2 (3)
H17A—C17—H17B107.5O8—C44—C43119.8 (3)
N4—C18—C19109.1 (3)O7—C44—C43114.9 (3)
N4—C18—H18A109.9C46—C45—C43120.3 (3)
C19—C18—H18A109.9C46—C45—H45119.9
N4—C18—H18B109.9C43—C45—H45119.9
C19—C18—H18B109.9C40—C46—C45120.9 (3)
H18A—C18—H18B108.3C40—C46—H46119.6
N3—C19—C18108.5 (3)C45—C46—H46119.6
N3—C19—H19A110.0C9—O1—C6119.8 (3)
C18—C19—H19A110.0C10—O2—C11116.4 (3)
N3—C19—H19B110.0C26—O3—C27118.1 (3)
C18—C19—H19B110.0C28—O4—C29118.8 (4)
H19A—C19—H19B108.4C39—O6—Ni1132.4 (2)
N3—C20—C21114.5 (3)C44—O7—Ni1ii130.8 (2)
N3—C20—H20A108.6C37—N1—C38116.6 (4)
C21—C20—H20A108.6C37—N1—Ni1105.4 (3)
N3—C20—H20B108.6C38—N1—Ni1115.7 (2)
C21—C20—H20B108.6C37—N1—H1N106 (3)
H20A—C20—H20B107.6C38—N1—H1N106 (3)
C26—C21—C22118.3 (4)Ni1—N1—H1N106 (3)
C26—C21—C20119.8 (4)C35—N2—C36110.4 (3)
C22—C21—C20121.8 (4)C35—N2—Ni1118.8 (2)
C21—C22—C23119.8 (5)C36—N2—Ni1107.4 (2)
C21—C22—H22120.1C35—N2—H2N112 (3)
C23—C22—H22120.1C36—N2—H2N112 (3)
C24—C23—C22120.2 (5)Ni1—N2—H2N96 (3)
C24—C23—H23119.9C19—N3—C20112.3 (3)
C22—C23—H23119.9C19—N3—Ni1104.5 (2)
C23—C24—C25121.1 (5)C20—N3—Ni1119.3 (2)
C23—C24—H24119.5C19—N3—H3N106 (3)
C25—C24—H24119.5C20—N3—H3N104 (3)
C26—C25—C24119.2 (5)Ni1—N3—H3N110 (3)
C26—C25—H25120.4C18—N4—C17112.2 (3)
C24—C25—H25120.4C18—N4—Ni1105.4 (2)
C25—C26—O3123.3 (4)C17—N4—Ni1118.3 (2)
C25—C26—C21121.3 (4)C18—N4—H4N109 (3)
O3—C26—C21115.4 (3)C17—N4—H4N110 (3)
O3—C27—C28110.2 (4)Ni1—N4—H4N101 (3)
O3—C27—H27A109.6
C6—C1—C2—C31.5 (7)C41—C40—C46—C45−2.4 (5)
C38—C1—C2—C3−177.8 (4)C39—C40—C46—C45174.2 (3)
C1—C2—C3—C40.3 (8)C43—C45—C46—C40−0.8 (6)
C2—C3—C4—C5−0.9 (8)C10—C9—O1—C6−178.7 (4)
C3—C4—C5—C6−0.4 (8)C5—C6—O1—C9−34.0 (6)
C4—C5—C6—C12.3 (7)C1—C6—O1—C9149.7 (4)
C4—C5—C6—O1−173.8 (4)C9—C10—O2—C11178.9 (4)
C2—C1—C6—C5−2.8 (6)C16—C11—O2—C10131.3 (4)
C38—C1—C6—C5176.5 (4)C12—C11—O2—C10−50.8 (6)
C2—C1—C6—O1173.6 (4)C25—C26—O3—C27−36.7 (7)
C38—C1—C6—O1−7.0 (6)C21—C26—O3—C27143.7 (4)
O1—C9—C10—O241.1 (6)C28—C27—O3—C26−160.0 (4)
C16—C11—C12—C13−1.6 (7)C27—C28—O4—C29176.2 (4)
O2—C11—C12—C13−179.3 (5)C34—C29—O4—C28140.7 (5)
C11—C12—C13—C14−0.5 (9)C30—C29—O4—C28−41.9 (7)
C12—C13—C14—C151.7 (10)O5—C39—O6—Ni1−4.2 (6)
C13—C14—C15—C16−0.9 (9)C40—C39—O6—Ni1175.8 (2)
C12—C11—C16—C152.4 (6)N1—Ni1—O6—C3978.3 (3)
O2—C11—C16—C15−179.8 (4)N3—Ni1—O6—C39−102.3 (3)
C12—C11—C16—C17−178.1 (4)N4—Ni1—O6—C39−19.1 (3)
O2—C11—C16—C17−0.2 (6)N2—Ni1—O6—C39159.4 (3)
C14—C15—C16—C11−1.1 (7)O8—C44—O7—Ni1ii14.3 (6)
C14—C15—C16—C17179.3 (5)C43—C44—O7—Ni1ii−163.6 (2)
C11—C16—C17—N483.3 (5)C36—C37—N1—C3881.0 (5)
C15—C16—C17—N4−97.2 (5)C36—C37—N1—Ni1−48.9 (5)
N4—C18—C19—N361.8 (4)C1—C38—N1—C3754.7 (5)
N3—C20—C21—C2671.6 (5)C1—C38—N1—Ni1179.6 (3)
N3—C20—C21—C22−110.4 (4)O6—Ni1—N1—C37122.4 (3)
C26—C21—C22—C23−0.6 (7)O7i—Ni1—N1—C37−57.8 (3)
C20—C21—C22—C23−178.6 (4)N4—Ni1—N1—C37−144.7 (3)
C21—C22—C23—C240.8 (8)N2—Ni1—N1—C3732.9 (3)
C22—C23—C24—C25−0.9 (9)O6—Ni1—N1—C38−8.1 (3)
C23—C24—C25—C260.8 (8)O7i—Ni1—N1—C38171.7 (3)
C24—C25—C26—O3179.8 (5)N4—Ni1—N1—C3884.8 (3)
C24—C25—C26—C21−0.6 (7)N2—Ni1—N1—C38−97.6 (3)
C22—C21—C26—C250.5 (7)C34—C35—N2—C36−66.6 (4)
C20—C21—C26—C25178.6 (4)C34—C35—N2—Ni1168.8 (3)
C22—C21—C26—O3−179.9 (4)C37—C36—N2—C35−142.5 (4)
C20—C21—C26—O3−1.8 (6)C37—C36—N2—Ni1−11.6 (5)
O3—C27—C28—O456.8 (7)O6—Ni1—N2—C3518.2 (3)
O4—C29—C30—C31−177.0 (4)O7i—Ni1—N2—C35−159.3 (3)
C34—C29—C30—C310.2 (7)N1—Ni1—N2—C35114.2 (3)
C29—C30—C31—C321.8 (7)N3—Ni1—N2—C35−71.2 (3)
C30—C31—C32—C33−1.4 (8)O6—Ni1—N2—C36−107.9 (3)
C31—C32—C33—C34−1.1 (7)O7i—Ni1—N2—C3674.6 (3)
O4—C29—C34—C33174.9 (4)N1—Ni1—N2—C36−11.9 (3)
C30—C29—C34—C33−2.4 (6)N3—Ni1—N2—C36162.6 (3)
O4—C29—C34—C35−4.8 (6)C18—C19—N3—C2083.7 (4)
C30—C29—C34—C35177.8 (4)C18—C19—N3—Ni1−47.0 (3)
C32—C33—C34—C292.9 (6)C21—C20—N3—C1961.7 (4)
C32—C33—C34—C35−177.4 (4)C21—C20—N3—Ni1−175.6 (3)
C29—C34—C35—N2−91.4 (4)O6—Ni1—N3—C19111.2 (2)
C33—C34—C35—N288.8 (5)O7i—Ni1—N3—C19−68.6 (2)
N2—C36—C37—N141.6 (6)N4—Ni1—N3—C1919.0 (2)
C6—C1—C38—N176.5 (5)N2—Ni1—N3—C19−158.5 (2)
C2—C1—C38—N1−104.2 (5)O6—Ni1—N3—C20−15.3 (3)
O5—C39—C40—C46166.5 (4)O7i—Ni1—N3—C20164.9 (3)
O6—C39—C40—C46−13.6 (5)N4—Ni1—N3—C20−107.5 (3)
O5—C39—C40—C41−16.9 (5)N2—Ni1—N3—C2075.0 (3)
O6—C39—C40—C41163.0 (3)C19—C18—N4—C1789.0 (4)
C46—C40—C41—C423.2 (5)C19—C18—N4—Ni1−41.1 (3)
C39—C40—C41—C42−173.5 (3)C16—C17—N4—C1869.4 (4)
C40—C41—C42—C43−0.8 (6)C16—C17—N4—Ni1−167.5 (2)
C41—C42—C43—C45−2.5 (5)O6—Ni1—N4—C18−77.3 (2)
C41—C42—C43—C44172.8 (3)O7i—Ni1—N4—C18100.2 (2)
C42—C43—C44—O8−177.9 (4)N1—Ni1—N4—C18−173.6 (2)
C45—C43—C44—O8−2.8 (6)N3—Ni1—N4—C1811.9 (2)
C42—C43—C44—O70.2 (5)O6—Ni1—N4—C17156.3 (2)
C45—C43—C44—O7175.3 (3)O7i—Ni1—N4—C17−26.1 (2)
C42—C43—C45—C463.2 (5)N1—Ni1—N4—C1760.0 (3)
C44—C43—C45—C46−172.0 (3)N3—Ni1—N4—C17−114.5 (3)
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.83 (2)2.58 (4)3.101 (4)122 (3)
N2—H2N···O8i0.81 (2)2.26 (2)3.003 (4)152 (4)
N3—H3N···O30.84 (2)2.47 (3)3.044 (4)127 (3)
N4—H4N···O50.83 (2)2.14 (3)2.862 (4)144 (4)
C10—H10A···O8iii0.972.403.359 (6)172
C12—H12···O8iii0.932.603.508 (6)166
C28—H28B···O2iv0.972.473.210 (7)133
C28—H28A···O5iv0.972.473.342 (6)149
C35—H35A···O40.972.382.761 (5)103
C37—H37B···O7i0.972.472.985 (6)113
C42—H42···O70.932.442.752 (4)100
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (iii) x−1/2, −y+1/2, z+1/2; (iv) x+1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.83 (2)2.58 (4)3.101 (4)122 (3)
N2—H2N···O8i0.81 (2)2.26 (2)3.003 (4)152 (4)
N3—H3N···O30.84 (2)2.47 (3)3.044 (4)127 (3)
N4—H4N···O50.83 (2)2.14 (3)2.862 (4)144 (4)
C10—H10A···O8ii0.972.403.359 (6)172
C12—H12···O8ii0.932.603.508 (6)166
C28—H28B···O2iii0.972.473.210 (7)133
C28—H28A···O5iii0.972.473.342 (6)149
C35—H35A···O40.972.382.761 (5)103
C37—H37B···O7i0.972.472.985 (6)113
C42—H42···O70.932.442.752 (4)100
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z+1/2; (iii) x+1, y, z.
Acknowledgements top

We thank the Analysis and Testing Foundation of Northeast Normal University for support.

references
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