supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers buy article online

at2393 scheme

Acta Cryst. (2007). E63, m2512-m2513    [ doi:10.1107/S160053680704353X ]

Bis{N-[2-(2-hydroxy-3-methoxybenzylamino)ethyl]-N'-(2-hydroxy-3-methoxybenzyl)ethane-1,2-diamine}nickel(II) dinitrate 1.25-hydrate

H.-T. Xia, Y.-F. Liu, D.-Q. Wang and S.-P. Yang

Abstract top

In the title compound, [Ni(C20H29N3O4)2](NO3)2·1.25H2O, the asymmetric unit consists of one cation, two nitrate anions, one complete water molecule and a half-occupancy water molecule lying on a twofold rotation axis. The Ni atom is situated in a distorted octahedral geometry. The molecules are linked into a three-dimensional network by O-H...O, N-H...O and C-H...O hydrogen bonds. Two nitrate O atoms are disordered over two sites in the ratio 0.64:0.36.

Comment top

We have recently reported crystal structure of nickel complex with diamine derivatives (Xia et al., 2007). We have now continued our studied in this area with the title complex, (I).

In (I), the asymmetric unit consists of one cation, two anions, one water molecules and one OH group. The Ni atom is six coordinated by four nitrogen and two oxygen atoms (Fig. 1). The equatorial plane are formed by N1, N4, O1 and O5 atoms, the axial positions are occupied by atoms O2 and N5. The Ni atom is shifted by 0.0217 (16)Å from the equatorial plane toward the axial N2 atom, and the coordinating N1, N4, O1and O5 atoms show the distortions with deviations of 0.0820 (14) Å, −0.0824 (13) Å, 0.0947 (16)Å and −0.944 (16)Å from the least-square N2O2 plane. The dihedral angles between equatorial plane and aryl rings are 20.03 (18)° for the ring (C2–C7), 71.03 (11)° for the ring (C10–C15), 24.12 (18)° for the ring (C22–C27) and 83.08 (10)° for the ring (C30–C35).

The molecules of the title complex (I) are linked into a three-dimensional network by O—H···O, N—H···O and C—H···O hydrogen bonds (Table 2).

Related literature top

For related literature, see: Venegas-Yazigi et al. (2006); Xia et al. (2007).

Experimental top

N-[2-(2-hydroxy-3-methoxybenzylamino)ethyl]-N'-[2-hydroxy-3-methoxybenzyl] ethane-1,2diamine (1 mmol) was dissolved in 10 ml e thanol, and 10 ml aqueous solution of nickel(II) nitrate (1 mmol) was added. The reaction mixture was stirred 2 h and filtered. The blue crystals of (I) suitable for X-ray diffraction was obtained by evaporation of an solution.

Refinement top

All H atoms were located in difference Fourier maps. The O13, O14, O13' and O14' bond to N8 of the nitrate were to be disordered over two sites. The coordinates of these two sites were refined with the occupancies tied to sum to unity. The site occupancies for O13, O14 and O13', O14' refined to 0.360 and 0.640, and at the same time O16 with attached H atoms was, found to be disordered in occupancies which were refined to half unity. H atoms bonded to C, N and O atoms were treated as riding atoms, with C—H distances of 0.93 Å (aryl), 0.96 Å (methyl), 0.97 Å(methylene), O—H distance of 0.85 Å and N—H distance of 0.91 Å (amine), and with Uiso(H) = 1.2Ueq(C,N) (aryl, methylene, amine) and 1.5Ueq(C,O) (methyl and water).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top
[Figure 1] Fig. 1. The structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are at the 30% probability level.
Bis{N-[2-(2-hydroxy-3-methoxybenzylamino)ethyl]-N'-(2-hydroxy-3-methoxybenzyl) ethane-1,2-diamine}nickel(II) dinitrate 1.25-hydrate top
Crystal data top
[Ni(C20H29N3O4)2](NO3)2·1.25H2OF000 = 4052
Mr = 3824.70Dx = 1.409 Mg m−3
Monoclinic, C2/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2390 reflections
a = 43.710 (3) Åθ = 2.6–18.2º
b = 9.5091 (16) ŵ = 0.51 mm−1
c = 28.476 (3) ÅT = 298 (2) K
β = 130.370 (3)ºBlock, blue
V = 9017.5 (18) Å30.40 × 0.16 × 0.13 mm
Z = 8
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer		7920 independent reflections
Radiation source: fine-focus sealed tube3683 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.074
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 1.4º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −51→51
Tmin = 0.823, Tmax = 0.937k = −11→11
22092 measured reflectionsl = −33→31
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064H-atom parameters constrained
wR(F2) = 0.154  w = 1/[σ2(Fo2) + (0.0509P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.016
7920 reflectionsΔρmax = 1.39 e Å−3
593 parametersΔρmin = −1.20 e Å−3
116 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Ni(C20H29N3O4)2](NO3)2·1.25H2OV = 9017.5 (18) Å3
Mr = 3824.70Z = 8
Monoclinic, C2/cMo Kα
a = 43.710 (3) ŵ = 0.51 mm−1
b = 9.5091 (16) ÅT = 298 (2) K
c = 28.476 (3) Å0.40 × 0.16 × 0.13 mm
β = 130.370 (3)º
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer		7920 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3683 reflections with I > 2σ(I)
Tmin = 0.823, Tmax = 0.937Rint = 0.074
22092 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.064116 restraints
wR(F2) = 0.154H-atom parameters constrained
S = 1.01Δρmax = 1.39 e Å−3
7920 reflectionsΔρmin = −1.20 e Å−3
593 parameters
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 > 2sigma(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*/UeqOcc. (<1)
Ni10.641419 (19)0.66303 (7)0.83507 (3)0.0421 (2)
N10.67961 (12)0.5637 (5)0.92197 (18)0.0470 (11)
H10.68240.62450.94920.056*
N20.60570 (12)0.4742 (4)0.81236 (18)0.0453 (11)
H20.59000.49790.82170.054*
N30.59205 (12)0.5073 (4)0.68534 (18)0.0503 (12)
H3A0.60040.58370.70950.060*
H3B0.60920.49430.67830.060*
N40.60783 (12)0.7801 (5)0.85042 (19)0.0495 (12)
H40.60880.73360.87930.059*
N50.67810 (11)0.8570 (4)0.87038 (17)0.0446 (11)
H50.70440.83110.89520.053*
N60.67847 (11)0.7963 (4)0.76456 (18)0.0457 (11)
H6A0.65270.80620.72990.055*
H6B0.67950.72510.78640.055*
N70.79795 (17)0.8175 (6)0.9440 (3)0.0647 (14)
N80.5515 (3)0.4732 (12)0.3733 (4)0.166 (3)
O10.67406 (9)0.5765 (4)0.81493 (14)0.0434 (9)
O20.68190 (10)0.4173 (4)0.74696 (16)0.0532 (10)
O30.59061 (11)0.4258 (4)0.58805 (17)0.0726 (12)
H30.60000.38980.57360.109*
O40.56196 (12)0.2248 (5)0.50398 (18)0.0799 (13)
O50.60564 (9)0.7372 (3)0.74682 (14)0.0394 (8)
O60.59622 (13)0.8973 (4)0.66216 (17)0.0809 (9)
O70.64853 (14)0.6522 (5)0.62992 (19)0.1009 (16)
H70.63680.62050.59530.151*
O80.62619 (13)0.7786 (4)0.52971 (19)0.0809 (9)
O90.77001 (13)0.8176 (6)0.9444 (2)0.0993 (17)
O100.83138 (14)0.7824 (5)0.9913 (2)0.0956 (16)
O110.79332 (12)0.8545 (5)0.8982 (2)0.0886 (15)
O120.5796 (2)0.4142 (10)0.3996 (3)0.198 (3)
O130.5197 (4)0.418 (3)0.3255 (11)0.239 (8)0.360 (10)
O140.5441 (6)0.554 (3)0.3961 (9)0.215 (6)0.360 (10)
O13'0.5460 (3)0.5510 (16)0.3304 (6)0.224 (5)0.640 (10)
O14'0.5220 (3)0.4543 (18)0.3637 (6)0.195 (4)0.640 (10)
O150.62322 (12)0.4501 (5)0.53586 (19)0.0917 (15)
H410.60750.43560.49720.138*
H420.64480.40930.54890.138*
O160.50000.2747 (19)0.75000.166 (7)0.50
H430.47950.31580.71820.250*0.50
C10.72074 (15)0.5365 (6)0.9449 (2)0.0542 (15)
H1A0.73670.49660.98600.065*
H1B0.73280.62560.94830.065*
C20.72261 (14)0.4396 (6)0.9053 (2)0.0449 (14)
C30.70035 (14)0.4694 (5)0.8429 (2)0.0408 (13)
C40.70488 (15)0.3824 (5)0.8079 (3)0.0425 (14)
C50.73178 (16)0.2706 (6)0.8355 (3)0.0525 (15)
H5A0.73510.21430.81240.063*
C60.75355 (17)0.2434 (6)0.8974 (3)0.0651 (17)
H60.77130.16790.91580.078*
C70.74916 (15)0.3271 (6)0.9317 (3)0.0580 (16)
H7A0.76420.30840.97350.070*
C80.68558 (16)0.3331 (6)0.7093 (2)0.0658 (17)
H8A0.71330.32680.72810.099*
H8B0.67060.37540.66930.099*
H8C0.67530.24060.70520.099*
C90.55143 (15)0.5370 (6)0.6253 (2)0.0548 (15)
H9A0.55300.61960.60700.066*
H9B0.53330.55860.63300.066*
C100.53406 (16)0.4178 (6)0.5800 (2)0.0466 (14)
C110.55433 (15)0.3678 (6)0.5615 (2)0.0492 (15)
C120.53789 (18)0.2648 (6)0.5165 (2)0.0553 (16)
C130.50100 (19)0.2091 (6)0.4911 (3)0.0640 (17)
H130.48990.13790.46180.077*
C140.48067 (18)0.2600 (7)0.5094 (3)0.0665 (18)
H140.45540.22440.49130.080*
C150.49687 (17)0.3610 (7)0.5532 (3)0.0558 (16)
H150.48280.39240.56550.067*
C160.5453 (2)0.1424 (7)0.4510 (3)0.095 (2)
H16A0.53800.05170.45590.143*
H16B0.56470.13120.44570.143*
H16C0.52190.18820.41550.143*
C170.65999 (16)0.4377 (6)0.9215 (2)0.0588 (16)
H17A0.64390.46380.93260.071*
H17B0.68030.37170.95220.071*
C180.63343 (16)0.3673 (6)0.8591 (2)0.0545 (15)
H18A0.64970.32790.85030.065*
H18B0.61830.29180.85860.065*
C190.57708 (16)0.4114 (6)0.7500 (2)0.0612 (16)
H19A0.55440.47440.72380.073*
H19B0.56710.32370.75290.073*
C200.59466 (17)0.3830 (6)0.7197 (2)0.0562 (16)
H20A0.62260.35620.75100.067*
H20B0.58050.30470.69140.067*
C210.56470 (15)0.7916 (6)0.7938 (2)0.0550 (16)
H21A0.54990.83490.80460.066*
H21B0.55390.69790.77840.066*
C220.55834 (14)0.8767 (5)0.7434 (2)0.0420 (14)
C230.57919 (14)0.8421 (6)0.7233 (2)0.0376 (12)
C240.57242 (15)0.9306 (6)0.6775 (2)0.0412 (13)
C250.54597 (14)1.0401 (6)0.6519 (2)0.0483 (14)
H250.54201.09430.62120.058*
C260.52528 (15)1.0701 (6)0.6717 (3)0.0543 (16)
H260.50691.14370.65410.065*
C270.53190 (15)0.9910 (6)0.7175 (3)0.0563 (16)
H270.51851.01360.73190.068*
C280.5962 (2)0.9959 (8)0.6247 (3)0.0952 (16)
H28A0.57040.99570.58400.143*
H28B0.61650.97060.62240.143*
H28C0.60171.08810.64220.143*
C290.70348 (15)0.7592 (6)0.7475 (2)0.0519 (15)
H29A0.70090.65910.73910.062*
H29B0.73140.77810.78260.062*
C300.69241 (16)0.8374 (6)0.6927 (3)0.0483 (14)
C310.66558 (19)0.7776 (7)0.6360 (3)0.0632 (17)
C320.6551 (2)0.8495 (8)0.5839 (3)0.0768 (19)
C330.6706 (2)0.9770 (8)0.5890 (4)0.080 (2)
H330.66271.02500.55420.095*
C340.6981 (2)1.0331 (7)0.6462 (4)0.081 (2)
H340.70971.11940.65050.097*
C350.70907 (18)0.9656 (7)0.6977 (3)0.0659 (17)
H350.72791.00650.73630.079*
C360.6178 (2)0.8226 (8)0.4753 (3)0.0952 (16)
H36A0.60710.91640.46540.143*
H36B0.59840.76030.44230.143*
H36C0.64200.82120.48110.143*
C370.62605 (16)0.9192 (6)0.8758 (3)0.0600 (16)
H37A0.62160.94900.90350.072*
H37B0.61330.98700.84250.072*
C380.67043 (16)0.9163 (6)0.9101 (2)0.0590 (16)
H38A0.68121.01090.92260.071*
H38B0.68390.85940.94700.071*
C390.67105 (15)0.9631 (6)0.8263 (2)0.0516 (15)
H39A0.68051.05380.84670.062*
H39B0.64240.97080.79220.062*
C400.69177 (15)0.9282 (6)0.8014 (2)0.0524 (15)
H40A0.68771.00580.77580.063*
H40B0.72040.92120.83580.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0469 (4)0.0429 (4)0.0366 (4)0.0007 (4)0.0271 (3)−0.0002 (3)
N10.055 (3)0.047 (3)0.041 (3)−0.001 (2)0.032 (2)−0.003 (2)
N20.048 (3)0.052 (3)0.038 (3)−0.002 (2)0.029 (2)0.003 (2)
N30.056 (3)0.045 (3)0.045 (3)−0.004 (2)0.031 (3)−0.008 (2)
N40.058 (3)0.056 (3)0.043 (3)−0.002 (3)0.036 (3)−0.002 (2)
N50.042 (2)0.046 (3)0.038 (3)0.003 (2)0.022 (2)0.001 (2)
N60.044 (3)0.046 (3)0.046 (3)0.003 (2)0.029 (2)0.010 (2)
N70.065 (4)0.077 (4)0.052 (4)−0.001 (3)0.038 (3)−0.012 (3)
N80.142 (7)0.275 (10)0.158 (8)−0.020 (7)0.132 (7)−0.078 (6)
O10.048 (2)0.041 (2)0.042 (2)0.0081 (18)0.0299 (19)0.0072 (18)
O20.068 (2)0.046 (2)0.054 (3)0.011 (2)0.044 (2)0.001 (2)
O30.060 (3)0.090 (3)0.068 (3)−0.019 (2)0.041 (2)−0.033 (2)
O40.076 (3)0.094 (4)0.064 (3)−0.022 (3)0.043 (3)−0.038 (3)
O50.045 (2)0.034 (2)0.042 (2)0.0036 (18)0.0297 (18)0.0019 (17)
O60.109 (2)0.073 (2)0.056 (2)0.0023 (19)0.051 (2)0.0137 (17)
O70.134 (4)0.068 (3)0.064 (3)−0.039 (3)0.048 (3)−0.003 (2)
O80.109 (2)0.073 (2)0.056 (2)0.0023 (19)0.051 (2)0.0137 (17)
O90.064 (3)0.153 (5)0.088 (4)−0.009 (3)0.053 (3)0.002 (3)
O100.071 (3)0.147 (5)0.059 (3)0.016 (3)0.037 (3)0.007 (3)
O110.090 (3)0.126 (4)0.061 (3)0.010 (3)0.054 (3)0.006 (3)
O120.130 (6)0.308 (9)0.181 (6)−0.021 (5)0.111 (6)−0.106 (6)
O130.168 (9)0.305 (12)0.206 (11)−0.010 (9)0.104 (9)−0.091 (10)
O140.173 (9)0.318 (12)0.193 (10)−0.016 (9)0.136 (8)−0.096 (9)
O13'0.172 (7)0.352 (11)0.211 (9)−0.043 (7)0.151 (7)−0.054 (8)
O14'0.143 (7)0.308 (11)0.206 (9)−0.025 (7)0.145 (7)−0.055 (8)
O150.089 (3)0.114 (4)0.093 (3)−0.015 (3)0.068 (3)−0.026 (3)
O160.201 (10)0.167 (11)0.208 (11)0.0000.166 (9)0.000
C10.054 (4)0.058 (4)0.034 (3)0.006 (3)0.021 (3)0.008 (3)
C20.038 (3)0.042 (4)0.045 (4)0.005 (3)0.022 (3)0.010 (3)
C30.039 (3)0.034 (3)0.046 (4)0.000 (3)0.026 (3)0.004 (3)
C40.048 (3)0.033 (4)0.044 (4)−0.005 (3)0.029 (3)−0.001 (3)
C50.057 (4)0.036 (4)0.068 (4)0.002 (3)0.042 (4)−0.002 (3)
C60.060 (4)0.049 (4)0.072 (5)0.015 (3)0.037 (4)0.016 (4)
C70.049 (4)0.058 (4)0.054 (4)0.011 (3)0.028 (3)0.018 (3)
C80.072 (4)0.070 (5)0.061 (4)0.012 (4)0.045 (4)−0.005 (4)
C90.061 (4)0.048 (4)0.045 (4)0.007 (3)0.030 (3)0.002 (3)
C100.049 (4)0.039 (4)0.041 (3)0.005 (3)0.025 (3)0.007 (3)
C110.038 (3)0.052 (4)0.038 (3)−0.005 (3)0.016 (3)−0.005 (3)
C120.055 (4)0.057 (4)0.039 (4)−0.002 (3)0.024 (3)−0.003 (3)
C130.065 (4)0.055 (4)0.042 (4)−0.008 (4)0.022 (4)−0.003 (3)
C140.054 (4)0.062 (5)0.055 (4)−0.009 (4)0.023 (4)0.001 (4)
C150.050 (4)0.066 (5)0.047 (4)0.015 (3)0.030 (3)0.014 (3)
C160.108 (5)0.095 (6)0.073 (5)−0.014 (5)0.055 (5)−0.037 (4)
C170.061 (4)0.074 (5)0.047 (4)0.006 (3)0.037 (3)0.013 (3)
C180.060 (4)0.044 (4)0.056 (4)0.000 (3)0.036 (3)0.008 (3)
C190.065 (4)0.062 (4)0.056 (4)−0.015 (3)0.039 (4)−0.003 (3)
C200.072 (4)0.040 (4)0.047 (4)−0.002 (3)0.034 (3)−0.001 (3)
C210.051 (4)0.064 (4)0.061 (4)0.006 (3)0.041 (4)0.001 (3)
C220.043 (3)0.040 (4)0.044 (3)0.005 (3)0.029 (3)−0.002 (3)
C230.040 (3)0.034 (3)0.039 (3)−0.006 (3)0.026 (3)−0.009 (3)
C240.045 (3)0.037 (4)0.043 (3)−0.008 (3)0.029 (3)−0.009 (3)
C250.046 (3)0.040 (4)0.049 (4)0.004 (3)0.027 (3)0.006 (3)
C260.042 (3)0.047 (4)0.062 (4)0.003 (3)0.028 (3)−0.006 (3)
C270.046 (4)0.066 (5)0.065 (4)0.005 (3)0.040 (3)−0.006 (4)
C280.119 (4)0.103 (4)0.073 (3)0.023 (3)0.066 (3)0.018 (3)
C290.054 (3)0.051 (4)0.063 (4)0.003 (3)0.043 (3)0.002 (3)
C300.053 (3)0.042 (4)0.067 (4)0.003 (3)0.046 (3)0.003 (3)
C310.077 (5)0.053 (5)0.065 (5)−0.007 (4)0.049 (4)0.001 (4)
C320.095 (5)0.067 (5)0.059 (5)−0.016 (4)0.046 (4)−0.015 (4)
C330.122 (6)0.056 (5)0.095 (6)0.014 (5)0.086 (6)0.015 (4)
C340.113 (6)0.053 (5)0.117 (7)−0.010 (4)0.093 (6)0.003 (5)
C350.077 (4)0.054 (5)0.083 (5)−0.008 (4)0.059 (4)−0.008 (4)
C360.119 (4)0.103 (4)0.073 (3)0.023 (3)0.066 (3)0.018 (3)
C370.072 (4)0.059 (4)0.058 (4)−0.001 (4)0.046 (4)−0.013 (3)
C380.074 (4)0.050 (4)0.052 (4)−0.006 (3)0.040 (4)−0.013 (3)
C390.063 (4)0.039 (4)0.053 (4)−0.006 (3)0.037 (3)−0.006 (3)
C400.060 (4)0.043 (4)0.051 (4)−0.005 (3)0.035 (3)−0.002 (3)
Geometric parameters (Å, °) top
Ni1—O12.025 (3)C9—C101.503 (7)
Ni1—O52.041 (3)C9—H9A0.9700
Ni1—N42.102 (4)C9—H9B0.9700
Ni1—N12.110 (4)C10—C111.376 (7)
Ni1—N22.184 (4)C10—C151.382 (7)
Ni1—N52.212 (4)C11—C121.386 (7)
N1—C171.468 (6)C12—C131.375 (7)
N1—C11.485 (6)C13—C141.376 (7)
N1—H10.9100C13—H130.9300
N2—C181.478 (6)C14—C151.356 (8)
N2—C191.483 (6)C14—H140.9300
N2—H20.9100C15—H150.9300
N3—C91.491 (6)C16—H16A0.9600
N3—C201.491 (6)C16—H16B0.9600
N3—H3A0.9000C16—H16C0.9600
N3—H3B0.9000C17—C181.510 (7)
N4—C371.470 (7)C17—H17A0.9700
N4—C211.492 (6)C17—H17B0.9700
N4—H40.9100C18—H18A0.9700
N5—C391.480 (6)C18—H18B0.9700
N5—C381.485 (6)C19—C201.504 (7)
N5—H50.9100C19—H19A0.9700
N6—C401.489 (6)C19—H19B0.9700
N6—C291.497 (5)C20—H20A0.9700
N6—H6A0.9000C20—H20B0.9700
N6—H6B0.9000C21—C221.510 (7)
N7—O91.229 (11)C21—H21A0.9700
N7—O101.229 (5)C21—H21B0.9700
N7—O111.235 (6)C22—C231.393 (6)
N8—O121.093 (10)C22—C271.399 (7)
N8—O14'1.148 (10)C23—C241.412 (7)
N8—O141.178 (12)C24—C251.364 (6)
N8—O131.266 (13)C25—C261.370 (6)
N8—O13'1.310 (12)C25—H250.9300
O1—C31.344 (5)C26—C271.364 (7)
O2—C41.369 (6)C26—H260.9300
O2—C81.428 (6)C27—H270.9300
O3—C111.355 (6)C28—H28A0.9600
O3—H30.8200C28—H28B0.9600
O4—C121.367 (6)C28—H28C0.9600
O4—C161.413 (6)C29—C301.499 (7)
O5—C231.333 (5)C29—H29A0.9700
O6—C241.402 (6)C29—H29B0.9700
O6—C281.421 (7)C30—C311.361 (7)
O7—C311.357 (7)C30—C351.379 (7)
O7—H70.8200C31—C321.414 (8)
O8—C321.381 (7)C32—C331.350 (8)
O8—C361.403 (6)C33—C341.359 (8)
O15—H410.8501C33—H330.9300
O15—H420.8501C34—C351.372 (8)
O16—H430.8500C34—H340.9300
C1—C21.500 (7)C35—H350.9300
C1—H1A0.9700C36—H36A0.9600
C1—H1B0.9700C36—H36B0.9600
C2—C71.388 (7)C36—H36C0.9600
C2—C31.393 (6)C37—C381.504 (7)
C3—C41.405 (6)C37—H37A0.9700
C4—C51.390 (7)C37—H37B0.9700
C5—C61.379 (7)C38—H38A0.9700
C5—H5A0.9300C38—H38B0.9700
C6—C71.367 (7)C39—C401.506 (6)
C6—H60.9300C39—H39A0.9700
C7—H7A0.9300C39—H39B0.9700
C8—H8A0.9600C40—H40A0.9700
C8—H8B0.9600C40—H40B0.9700
C8—H8C0.9600
O1—Ni1—O584.85 (12)C15—C14—C13121.2 (6)
O1—Ni1—N4171.59 (16)C15—C14—H14119.4
O5—Ni1—N489.52 (15)C13—C14—H14119.4
O1—Ni1—N189.02 (14)C14—C15—C10120.7 (6)
O5—Ni1—N1172.66 (15)C14—C15—H15119.7
N4—Ni1—N197.00 (16)C10—C15—H15119.7
O1—Ni1—N294.69 (14)O4—C16—H16A109.5
O5—Ni1—N295.09 (14)O4—C16—H16B109.5
N4—Ni1—N292.02 (17)H16A—C16—H16B109.5
N1—Ni1—N281.37 (16)O4—C16—H16C109.5
O1—Ni1—N591.79 (14)H16A—C16—H16C109.5
O5—Ni1—N591.33 (14)H16B—C16—H16C109.5
N4—Ni1—N582.08 (16)N1—C17—C18111.8 (4)
N1—Ni1—N592.89 (16)N1—C17—H17A109.3
N2—Ni1—N5171.25 (15)C18—C17—H17A109.3
C17—N1—C1113.3 (4)N1—C17—H17B109.3
C17—N1—Ni1110.0 (3)C18—C17—H17B109.3
C1—N1—Ni1114.0 (3)H17A—C17—H17B107.9
C17—N1—H1106.3N2—C18—C17108.2 (5)
C1—N1—H1106.3N2—C18—H18A110.1
Ni1—N1—H1106.3C17—C18—H18A110.1
C18—N2—C19111.4 (4)N2—C18—H18B110.1
C18—N2—Ni1106.7 (3)C17—C18—H18B110.1
C19—N2—Ni1124.9 (3)H18A—C18—H18B108.4
C18—N2—H2103.9N2—C19—C20114.3 (4)
C19—N2—H2103.9N2—C19—H19A108.7
Ni1—N2—H2103.9C20—C19—H19A108.7
C9—N3—C20115.5 (4)N2—C19—H19B108.7
C9—N3—H3A108.4C20—C19—H19B108.7
C20—N3—H3A108.4H19A—C19—H19B107.6
C9—N3—H3B108.4N3—C20—C19112.5 (5)
C20—N3—H3B108.4N3—C20—H20A109.1
H3A—N3—H3B107.5C19—C20—H20A109.1
C37—N4—C21111.6 (4)N3—C20—H20B109.1
C37—N4—Ni1110.5 (3)C19—C20—H20B109.1
C21—N4—Ni1112.2 (3)H20A—C20—H20B107.8
C37—N4—H4107.4N4—C21—C22113.1 (4)
C21—N4—H4107.4N4—C21—H21A109.0
Ni1—N4—H4107.4C22—C21—H21A109.0
C39—N5—C38111.3 (4)N4—C21—H21B109.0
C39—N5—Ni1119.4 (3)C22—C21—H21B109.0
C38—N5—Ni1102.0 (3)H21A—C21—H21B107.8
C39—N5—H5107.9C23—C22—C27120.3 (5)
C38—N5—H5107.9C23—C22—C21119.9 (5)
Ni1—N5—H5107.9C27—C22—C21119.8 (5)
C40—N6—C29113.1 (4)O5—C23—C22123.7 (5)
C40—N6—H6A109.0O5—C23—C24120.4 (4)
C29—N6—H6A109.0C22—C23—C24115.9 (5)
C40—N6—H6B109.0C25—C24—O6123.3 (5)
C29—N6—H6B109.0C25—C24—C23123.1 (5)
H6A—N6—H6B107.8O6—C24—C23113.5 (5)
O9—N7—O10118.3 (6)C24—C25—C26119.7 (5)
O9—N7—O11121.7 (6)C24—C25—H25120.1
O10—N7—O11120.0 (5)C26—C25—H25120.1
O12—N8—O14'132.4 (14)C27—C26—C25119.4 (5)
O12—N8—O14123.0 (13)C27—C26—H26120.3
O14'—N8—O1464.3 (11)C25—C26—H26120.3
O12—N8—O13119.4 (14)C26—C27—C22121.5 (5)
O14'—N8—O1353.0 (13)C26—C27—H27119.2
O14—N8—O13111.0 (12)C22—C27—H27119.2
O12—N8—O13'112.0 (9)O6—C28—H28A109.5
O14'—N8—O13'111.7 (11)O6—C28—H28B109.5
O14—N8—O13'101 (2)H28A—C28—H28B109.5
O13—N8—O13'79.6 (19)O6—C28—H28C109.5
C3—O1—Ni1128.9 (3)H28A—C28—H28C109.5
C4—O2—C8118.0 (4)H28B—C28—H28C109.5
C11—O3—H3109.5N6—C29—C30114.2 (4)
C12—O4—C16118.8 (5)N6—C29—H29A108.7
C23—O5—Ni1126.9 (3)C30—C29—H29A108.7
C24—O6—C28116.5 (5)N6—C29—H29B108.7
C31—O7—H7109.8C30—C29—H29B108.7
C32—O8—C36119.0 (5)H29A—C29—H29B107.6
H41—O15—H42103.3C31—C30—C35118.9 (6)
N1—C1—C2114.6 (4)C31—C30—C29118.5 (6)
N1—C1—H1A108.6C35—C30—C29122.6 (6)
C2—C1—H1A108.6O7—C31—C30120.0 (6)
N1—C1—H1B108.6O7—C31—C32120.9 (6)
C2—C1—H1B108.6C30—C31—C32119.2 (6)
H1A—C1—H1B107.6C33—C32—O8126.2 (7)
C7—C2—C3119.8 (5)C33—C32—C31121.6 (6)
C7—C2—C1120.0 (5)O8—C32—C31112.1 (6)
C3—C2—C1120.0 (5)C32—C33—C34118.3 (7)
O1—C3—C2122.2 (5)C32—C33—H33120.9
O1—C3—C4119.0 (5)C34—C33—H33120.9
C2—C3—C4118.7 (5)C33—C34—C35121.5 (7)
O2—C4—C5124.1 (5)C33—C34—H34119.2
O2—C4—C3115.6 (5)C35—C34—H34119.2
C5—C4—C3120.4 (5)C34—C35—C30120.5 (6)
C6—C5—C4119.8 (5)C34—C35—H35119.7
C6—C5—H5A120.1C30—C35—H35119.7
C4—C5—H5A120.1O8—C36—H36A109.5
C7—C6—C5120.2 (6)O8—C36—H36B109.5
C7—C6—H6119.9H36A—C36—H36B109.5
C5—C6—H6119.9O8—C36—H36C109.5
C6—C7—C2121.1 (5)H36A—C36—H36C109.5
C6—C7—H7A119.5H36B—C36—H36C109.5
C2—C7—H7A119.5N4—C37—C38111.3 (5)
O2—C8—H8A109.5N4—C37—H37A109.4
O2—C8—H8B109.5C38—C37—H37A109.4
H8A—C8—H8B109.5N4—C37—H37B109.4
O2—C8—H8C109.5C38—C37—H37B109.4
H8A—C8—H8C109.5H37A—C37—H37B108.0
H8B—C8—H8C109.5N5—C38—C37110.1 (4)
N3—C9—C10114.0 (4)N5—C38—H38A109.6
N3—C9—H9A108.8C37—C38—H38A109.6
C10—C9—H9A108.8N5—C38—H38B109.6
N3—C9—H9B108.8C37—C38—H38B109.6
C10—C9—H9B108.8H38A—C38—H38B108.1
H9A—C9—H9B107.7N5—C39—C40113.0 (4)
C11—C10—C15118.3 (5)N5—C39—H39A109.0
C11—C10—C9119.8 (5)C40—C39—H39A109.0
C15—C10—C9121.8 (5)N5—C39—H39B109.0
O3—C11—C10117.2 (5)C40—C39—H39B109.0
O3—C11—C12121.5 (5)H39A—C39—H39B107.8
C10—C11—C12121.3 (5)N6—C40—C39115.9 (4)
O4—C12—C13126.4 (6)N6—C40—H40A108.3
O4—C12—C11114.3 (5)C39—C40—H40A108.3
C13—C12—C11119.3 (6)N6—C40—H40B108.3
C12—C13—C14119.3 (6)C39—C40—H40B108.3
C12—C13—H13120.4H40A—C40—H40B107.4
C14—C13—H13120.4
O1—Ni1—N1—C17−101.5 (3)C16—O4—C12—C11−167.4 (5)
N4—Ni1—N1—C1784.4 (3)O3—C11—C12—O42.4 (8)
N2—Ni1—N1—C17−6.6 (3)C10—C11—C12—O4−179.0 (5)
N5—Ni1—N1—C17166.8 (3)O3—C11—C12—C13179.8 (5)
O1—Ni1—N1—C127.1 (4)C10—C11—C12—C13−1.6 (8)
N4—Ni1—N1—C1−147.0 (4)O4—C12—C13—C14179.1 (5)
N2—Ni1—N1—C1122.0 (4)C11—C12—C13—C142.0 (9)
N5—Ni1—N1—C1−64.7 (4)C12—C13—C14—C15−1.9 (9)
O1—Ni1—N2—C1867.5 (3)C13—C14—C15—C101.3 (9)
O5—Ni1—N2—C18152.8 (3)C11—C10—C15—C14−0.8 (8)
N4—Ni1—N2—C18−117.5 (3)C9—C10—C15—C14175.5 (5)
N1—Ni1—N2—C18−20.7 (3)C1—N1—C17—C18−95.6 (5)
O1—Ni1—N2—C19−64.8 (4)Ni1—N1—C17—C1833.3 (5)
O5—Ni1—N2—C1920.4 (4)C19—N2—C18—C17−177.0 (4)
N4—Ni1—N2—C19110.1 (4)Ni1—N2—C18—C1743.6 (5)
N1—Ni1—N2—C19−153.1 (4)N1—C17—C18—N2−52.6 (6)
O5—Ni1—N4—C37−92.2 (3)C18—N2—C19—C20−77.6 (6)
N1—Ni1—N4—C3791.1 (4)Ni1—N2—C19—C2053.0 (6)
N2—Ni1—N4—C37172.7 (3)C9—N3—C20—C19−75.2 (5)
N5—Ni1—N4—C37−0.8 (3)N2—C19—C20—N3−87.0 (6)
O5—Ni1—N4—C2133.0 (3)C37—N4—C21—C2258.1 (6)
N1—Ni1—N4—C21−143.6 (3)Ni1—N4—C21—C22−66.5 (5)
N2—Ni1—N4—C21−62.0 (3)N4—C21—C22—C2353.5 (6)
N5—Ni1—N4—C21124.5 (3)N4—C21—C22—C27−125.7 (5)
O1—Ni1—N5—C3978.0 (3)Ni1—O5—C23—C22−30.3 (6)
O5—Ni1—N5—C39−6.9 (3)Ni1—O5—C23—C24146.3 (4)
N4—Ni1—N5—C39−96.2 (4)C27—C22—C23—O5178.1 (4)
N1—Ni1—N5—C39167.1 (3)C21—C22—C23—O5−1.1 (7)
O1—Ni1—N5—C38−158.9 (3)C27—C22—C23—C241.4 (7)
O5—Ni1—N5—C38116.2 (3)C21—C22—C23—C24−177.8 (4)
N4—Ni1—N5—C3826.9 (3)C28—O6—C24—C259.0 (7)
N1—Ni1—N5—C38−69.8 (3)C28—O6—C24—C23−169.4 (5)
O5—Ni1—O1—C3−159.8 (4)O5—C23—C24—C25−179.6 (4)
N1—Ni1—O1—C316.1 (4)C22—C23—C24—C25−2.8 (7)
N2—Ni1—O1—C3−65.1 (4)O5—C23—C24—O6−1.1 (6)
N5—Ni1—O1—C3109.0 (4)C22—C23—C24—O6175.7 (4)
O1—Ni1—O5—C23−161.8 (4)O6—C24—C25—C26−176.7 (5)
N4—Ni1—O5—C2312.0 (4)C23—C24—C25—C261.6 (8)
N2—Ni1—O5—C23104.0 (4)C24—C25—C26—C271.0 (8)
N5—Ni1—O5—C23−70.1 (4)C25—C26—C27—C22−2.2 (8)
C17—N1—C1—C264.7 (6)C23—C22—C27—C261.0 (8)
Ni1—N1—C1—C2−62.1 (5)C21—C22—C27—C26−179.8 (5)
N1—C1—C2—C7−130.7 (5)C40—N6—C29—C30−81.1 (6)
N1—C1—C2—C355.0 (7)N6—C29—C30—C31−92.7 (6)
Ni1—O1—C3—C2−29.2 (6)N6—C29—C30—C3588.9 (6)
Ni1—O1—C3—C4149.2 (4)C35—C30—C31—O7−179.4 (5)
C7—C2—C3—O1179.6 (4)C29—C30—C31—O72.2 (8)
C1—C2—C3—O1−6.1 (7)C35—C30—C31—C32−1.1 (9)
C7—C2—C3—C41.2 (7)C29—C30—C31—C32−179.5 (5)
C1—C2—C3—C4175.5 (5)C36—O8—C32—C3315.4 (10)
C8—O2—C4—C50.5 (7)C36—O8—C32—C31−168.7 (5)
C8—O2—C4—C3179.4 (4)O7—C31—C32—C33177.4 (6)
O1—C3—C4—O21.1 (7)C30—C31—C32—C33−1.0 (10)
C2—C3—C4—O2179.6 (4)O7—C31—C32—O81.3 (9)
O1—C3—C4—C5−179.9 (4)C30—C31—C32—O8−177.1 (5)
C2—C3—C4—C5−1.4 (7)O8—C32—C33—C34178.1 (6)
O2—C4—C5—C6−179.8 (5)C31—C32—C33—C342.5 (10)
C3—C4—C5—C61.3 (8)C32—C33—C34—C35−2.1 (10)
C4—C5—C6—C7−0.9 (9)C33—C34—C35—C300.1 (10)
C5—C6—C7—C20.7 (9)C31—C30—C35—C341.5 (9)
C3—C2—C7—C6−0.9 (8)C29—C30—C35—C34179.8 (5)
C1—C2—C7—C6−175.2 (5)C21—N4—C37—C38−152.0 (4)
C20—N3—C9—C10−58.8 (6)Ni1—N4—C37—C38−26.4 (5)
N3—C9—C10—C11−58.7 (7)C39—N5—C38—C3779.4 (5)
N3—C9—C10—C15125.1 (5)Ni1—N5—C38—C37−49.1 (5)
C15—C10—C11—O3179.6 (5)N4—C37—C38—N553.2 (6)
C9—C10—C11—O33.2 (7)C38—N5—C39—C40159.5 (4)
C15—C10—C11—C121.0 (8)Ni1—N5—C39—C40−82.1 (5)
C9—C10—C11—C12−175.4 (5)C29—N6—C40—C39−173.2 (4)
C16—O4—C12—C1315.4 (9)N5—C39—C40—N663.0 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O9i0.912.383.122 (6)139
N1—H1···O10i0.912.313.163 (6)156
N2—H2···O13'ii0.912.142.976 (11)152
N4—H4···O12ii0.912.213.021 (8)148
O15—H42···O10iii0.852.323.013 (6)138
O15—H42···O11iii0.852.142.965 (6)163
C9—H9B···O14'iv0.972.483.420 (10)163
C17—H17A···O12ii0.972.593.445 (9)147
C34—H34···O11v0.932.593.419 (8)149
O16—H43···O13'iv0.851.662.464 (17)156
O3—H3···O150.821.982.653 (5)139
O3—H3···O40.822.212.659 (5)115
N3—H3A···O50.901.732.617 (5)168
N3—H3B···O20.902.533.211 (5)133
N3—H3B···O30.902.232.838 (5)124
N5—H5···O90.912.243.123 (6)165
N6—H6A···O50.902.492.936 (5)111
N6—H6A···O60.902.102.961 (6)161
N6—H6B···O10.901.722.612 (5)169
O7—H7···O80.822.202.633 (6)113
O7—H7···O150.822.132.872 (6)151
O15—H41···O120.852.213.037 (8)166
C1—H1B···O90.972.493.438 (7)165
C29—H29A···O20.972.503.382 (6)151
C29—H29A···O70.972.392.757 (7)102
C40—H40B···O90.972.563.369 (7)141
C40—H40B···O110.972.533.456 (7)160
C39—H39B···O50.972.553.087 (6)115
Symmetry codes: (i) −x+3/2, −y+3/2, −z+2; (ii) x, −y+1, z+1/2; (iii) −x+3/2, y−1/2, −z+3/2; (iv) −x+1, −y+1, −z+1; (v) −x+3/2, y+1/2, −z+3/2.
Selected geometric parameters (Å, °) top
Ni1—O12.025 (3)Ni1—N12.110 (4)
Ni1—O52.041 (3)Ni1—N22.184 (4)
Ni1—N42.102 (4)Ni1—N52.212 (4)
O1—Ni1—O584.85 (12)N4—Ni1—N292.02 (17)
O1—Ni1—N4171.59 (16)N1—Ni1—N281.37 (16)
O5—Ni1—N489.52 (15)O1—Ni1—N591.79 (14)
O1—Ni1—N189.02 (14)O5—Ni1—N591.33 (14)
O5—Ni1—N1172.66 (15)N4—Ni1—N582.08 (16)
N4—Ni1—N197.00 (16)N1—Ni1—N592.89 (16)
O1—Ni1—N294.69 (14)N2—Ni1—N5171.25 (15)
O5—Ni1—N295.09 (14)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O9i0.912.383.122 (6)139
N1—H1···O10i0.912.313.163 (6)156
N2—H2···O13'ii0.912.142.976 (11)152
N4—H4···O12ii0.912.213.021 (8)148
O15—H42···O10iii0.852.323.013 (6)138
O15—H42···O11iii0.852.142.965 (6)163
C9—H9B···O14'iv0.972.483.420 (10)163
C17—H17A···O12ii0.972.593.445 (9)147
C34—H34···O11v0.932.593.419 (8)149
O16—H43···O13'iv0.851.662.464 (17)156
O3—H3···O150.821.982.653 (5)139
O3—H3···O40.822.212.659 (5)115
N3—H3A···O50.901.732.617 (5)168
N3—H3B···O20.902.533.211 (5)133
N3—H3B···O30.902.232.838 (5)124
N5—H5···O90.912.243.123 (6)165
N6—H6A···O50.902.492.936 (5)111
N6—H6A···O60.902.102.961 (6)161
N6—H6B···O10.901.722.612 (5)169
O7—H7···O80.822.202.633 (6)113
O7—H7···O150.822.132.872 (6)151
O15—H41···O120.852.213.037 (8)166
C1—H1B···O90.972.493.438 (7)165
C29—H29A···O20.972.503.382 (6)151
C29—H29A···O70.972.392.757 (7)102
C40—H40B···O90.972.563.369 (7)141
C40—H40B···O110.972.533.456 (7)160
C39—H39B···O50.972.553.087 (6)115
Symmetry codes: (i) −x+3/2, −y+3/2, −z+2; (ii) x, −y+1, z+1/2; (iii) −x+3/2, y−1/2, −z+3/2; (iv) −x+1, −y+1, −z+1; (v) −x+3/2, y+1/2, −z+3/2.
Acknowledgements top

We acknowledge the financial support of the Huaihai Institute of Technology Science Foundation.

references
References top

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (1997a). SHELXL97 and SHELXS97. University of Göttingen, Germany.

Sheldrick, G. M. (1997b). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.

Siemens. (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Venegas-Yazigi, D., Cortés, S., Paredes-García, V., Paňa, O., Ibaňez, A., Baggio, R. & Spodine, E. (2006). Polyhedron, 25, 2072–2082.

Xia, H.-T., Liu, Y.-F., Wang, D.-Q. & Yang, S.-P. (2007). Acta Cryst. E63, m1162–m1164.