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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): m438.
Published online 2008 January 30. doi:  10.1107/S1600536808002900
PMCID: PMC2960234

[3-Hydr­oxy-N′-(2-oxidobenzyl­idene)-2-naphthohydrazidato-κ3 O,N,O′]tris­(pyridine-κN)nickel(II) pyridine tris­olvate

Abstract

The asymmetric unit of the crystal structure of the title complex, [Ni(C18H12N2O3)(C5H5N)3]·3C5H5N, contains two independent NiII complex mol­ecules and six uncoordinated pyridine mol­ecules. Each NiII atom is coordinated by two O and four N atoms, from three pyridine and a chelating 3-hydr­oxy-N′-(2-oxidobenzyl­idene)-2-naphthohydrazide dianionic ligand, with a distorted octa­hedral geometry. Intra­molecular O—H(...)N hydrogen bonding exists in both complex mol­ecules but no inter­molecular hydrogen bonding is observed in the crystal structure.

Related literature

For general background, see Samanta et al. (2007 [triangle]). For the specific biological activities of hydrazones, see Bernhardt et al. (2006 [triangle]). For the crystal structure of a Ni complex with a related hydrazone derivative, see: Kang et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m438-scheme1.jpg

Experimental

Crystal data

  • [Ni(C18H12N2O3)(C5H5N)3]·3C5H5N
  • M r = 837.59
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m438-efi1.jpg
  • a = 18.370 (2) Å
  • b = 27.720 (3) Å
  • c = 16.862 (2) Å
  • β = 90.378 (2)°
  • V = 8586.3 (18) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.50 mm−1
  • T = 298 (2) K
  • 0.50 × 0.40 × 0.28 mm

Data collection

  • Bruker SMART 1000 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.787, T max = 0.872
  • 35434 measured reflections
  • 14836 independent reflections
  • 5715 reflections with I > 2σ(I)
  • R int = 0.079

Refinement

  • R[F 2 > 2σ(F 2)] = 0.081
  • wR(F 2) = 0.321
  • S = 1.00
  • 14836 reflections
  • 1081 parameters
  • H-atom parameters constrained
  • Δρmax = 0.77 e Å−3
  • Δρmin = −0.68 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808002900/xu2364sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002900/xu2364Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge the support of the National Natural Science Foundation of China (grant No. 20671048).

supplementary crystallographic information

Comment

Hydrazones and their metal complexes occupy special place due to their chelating capability, structure flexibility, magnetic properties (Samanta et al., 2007) and their biological activities (Bernhardt et al., 2006). As an extension of our work on the structural characterization of hydrazone derivatives (Kang et al., 2007), the title complex, (I), was synthesized and charaterized.

As shown in Fig. 1., the asymmetric unit contains two crystallographically independent NiII complex molecules, together with six pyridine solvent molecules. structures of the two independent molecules are almost the same, with only few differences in bond lengths and angles (Table 1). In Ni1-complex molecule, the Ni1 atom is coordinated by a L- ligand [H2L = 3-hydroxy-N'-(2-oxidobenzylidene)-2-naphthohydrazide] and three pyridine molecules with a distorted octahedron geometry. The L- is coordinated to the Ni atom as a tridentate ligand via N atom of the azomethine, O atom of the the hydroxyl and O atom of the phenolate. The tridentate binding leads to one five-numbered chelate ring Ni—N—N—C—O and one six-numbered chelate ring Ni—N—C—C—C—O. The dihedral angle between the two rings is 1.3 (8)°. The atoms N2, O3, N3 and O1 constitute the equatorial plane, with the mean deviation from plane 0.0055 (6) Å. The angles N2—Ni1—N3 and O3—Ni1—O1 are 174.6 (3) and 170.0 (2)°, respectively. The axial positions are occupied by the atoms N5 and N4. The angle of N5—Ni1—N4 is 173.9 (3)°. In the Ni2-complex, the Ni2 atom is also coordinated by two O and four N atoms in a distorted octahedron geometry. There are two intramolecular O2—H2···N1 and O5—H5···N6 hydrogen bonds (Table 2).

Experimental

To a vigorously stirred 20 ml dimethylformamide solution of H2L (0.077 g, 0.25 mmol) and KOH (0.014 g, 0.25 mmol), 10 ml pyridine solution of Ni(OAC)2.4H2O (0.062 g, 0.25 mmol) was added dropwise. And then the mixture was stirred for 4 h and then filtered. Single crystals were obtained from filtrate after two weeks.

Refinement

All H atoms were placed in geometrically idealized positions with O—H = 0.82 and C—H = 0.93 Å, and treated as riding on their parent atoms, with Uiso(H) = 1.5Ueq(O) and Uiso(H) = 1.2Ueq(C). Due to the poor quality of the single-crystal, the accuracye of the structure analysis is relatively low.

Figures

Fig. 1.
The structure of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering scheme. C-bound H atoms have been omitted for clarity.

Crystal data

[Ni(C18H12N2O3)(C5H5N)3]·3C5H5NF000 = 3504
Mr = 837.59Dx = 1.296 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4738 reflections
a = 18.370 (2) Åθ = 2.2–20.5º
b = 27.720 (3) ŵ = 0.50 mm1
c = 16.862 (2) ÅT = 298 (2) K
β = 90.378 (2)ºBlock, red
V = 8586.3 (18) Å30.50 × 0.40 × 0.28 mm
Z = 8

Data collection

Bruker SMART 1000 CCD area-detector diffractometer14836 independent reflections
Radiation source: fine-focus sealed tube5715 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.079
T = 298(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −21→16
Tmin = 0.787, Tmax = 0.872k = −29→32
35434 measured reflectionsl = −18→20

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.081H-atom parameters constrained
wR(F2) = 0.321  w = 1/[σ2(Fo2) + (0.1595P)2 + 3.0585P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
14836 reflectionsΔρmax = 0.77 e Å3
1081 parametersΔρmin = −0.68 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
Ni10.03268 (5)0.27695 (3)0.16059 (6)0.0517 (3)
Ni20.53241 (5)0.23392 (4)0.94731 (6)0.0552 (3)
O10.0273 (3)0.20424 (18)0.1821 (3)0.0562 (14)
O2−0.0647 (3)0.1242 (2)−0.0051 (4)0.085 (2)
H2−0.05920.1535−0.00080.128*
O30.0299 (3)0.34493 (17)0.1214 (3)0.0566 (14)
O40.5270 (3)0.16541 (18)0.9945 (3)0.0559 (14)
O50.4283 (4)0.1613 (2)1.2177 (4)0.092 (2)
H50.43390.18411.18720.137*
O60.5316 (3)0.30395 (19)0.9206 (3)0.0639 (15)
N1−0.0219 (3)0.2040 (2)0.0557 (4)0.0529 (16)
N2−0.0118 (3)0.2540 (2)0.0596 (4)0.0510 (16)
N30.0777 (3)0.2945 (2)0.2702 (4)0.0568 (17)
N4−0.0738 (3)0.2859 (2)0.2166 (4)0.0572 (17)
N50.1433 (4)0.2687 (3)0.1177 (4)0.0649 (19)
N60.4775 (3)0.2078 (3)1.1004 (4)0.0607 (18)
N70.4885 (3)0.2480 (2)1.0519 (4)0.0585 (18)
N80.5757 (3)0.2122 (3)0.8402 (4)0.0600 (18)
N90.4274 (3)0.2233 (2)0.8922 (4)0.0599 (18)
N100.6439 (4)0.2400 (3)0.9913 (4)0.0653 (19)
N110.7971 (10)0.4330 (9)0.0620 (15)0.198 (8)
N120.3091 (6)0.4220 (5)0.5294 (10)0.129 (4)
N130.2613 (13)0.4331 (9)0.1332 (15)0.290 (12)
N140.1890 (7)0.6197 (7)0.2569 (12)0.146 (6)
N150.1976 (5)0.5617 (5)0.6056 (8)0.121 (4)
N160.2501 (13)0.4189 (7)0.9308 (12)0.222 (8)
C1−0.0008 (4)0.1827 (3)0.1222 (5)0.051 (2)
C20.0190 (4)0.1045 (3)0.1887 (5)0.055 (2)
H2A0.03890.12190.23070.066*
C3−0.0072 (4)0.1289 (3)0.1241 (5)0.052 (2)
C4−0.0395 (4)0.1023 (3)0.0607 (6)0.063 (2)
C5−0.0434 (4)0.0526 (3)0.0651 (6)0.072 (3)
H5A−0.06510.03550.02390.087*
C6−0.0152 (4)0.0274 (3)0.1310 (6)0.064 (2)
C70.0169 (4)0.0542 (3)0.1936 (5)0.060 (2)
C80.0464 (5)0.0287 (3)0.2587 (6)0.074 (3)
H80.06730.04570.30050.089*
C90.0449 (5)−0.0205 (3)0.2613 (7)0.083 (3)
H90.0643−0.03680.30480.099*
C100.0138 (5)−0.0465 (4)0.1976 (7)0.086 (3)
H100.0134−0.08000.19890.103*
C11−0.0155 (5)−0.0231 (3)0.1343 (7)0.078 (3)
H11−0.0360−0.04070.09290.094*
C12−0.0321 (4)0.2787 (3)0.0004 (5)0.053 (2)
H12−0.05250.2624−0.04260.063*
C13−0.0259 (4)0.3301 (3)−0.0051 (5)0.053 (2)
C140.0030 (4)0.3601 (3)0.0542 (5)0.056 (2)
C150.0044 (4)0.4102 (3)0.0385 (6)0.067 (2)
H150.02380.43080.07660.080*
C16−0.0216 (5)0.4290 (3)−0.0302 (6)0.076 (3)
H16−0.01960.4622−0.03800.091*
C17−0.0508 (5)0.4001 (3)−0.0887 (6)0.080 (3)
H17−0.06860.4131−0.13580.096*
C18−0.0528 (4)0.3512 (3)−0.0749 (5)0.066 (2)
H18−0.07290.3313−0.11370.079*
C190.0938 (5)0.3392 (3)0.2881 (6)0.085 (3)
H190.08710.36270.24950.102*
C200.1196 (6)0.3529 (4)0.3598 (7)0.105 (4)
H200.13080.38500.36970.126*
C210.1289 (6)0.3191 (5)0.4171 (7)0.100 (4)
H210.14470.32770.46770.120*
C220.1144 (6)0.2720 (4)0.3985 (6)0.095 (3)
H220.12240.24770.43570.114*
C230.0886 (5)0.2611 (4)0.3260 (6)0.084 (3)
H230.07790.22910.31420.100*
C24−0.1053 (5)0.2519 (4)0.2568 (6)0.087 (3)
H24−0.08480.22120.25520.104*
C25−0.1672 (6)0.2583 (5)0.3017 (7)0.106 (4)
H25−0.18650.23260.33010.128*
C26−0.1987 (7)0.3011 (5)0.3039 (8)0.119 (4)
H26−0.23930.30660.33540.143*
C27−0.1702 (7)0.3369 (5)0.2589 (9)0.127 (5)
H27−0.19260.36690.25610.152*
C28−0.1061 (5)0.3277 (4)0.2166 (7)0.095 (3)
H28−0.08570.35260.18720.114*
C290.1770 (6)0.3032 (4)0.0792 (7)0.101 (4)
H290.15170.33180.07020.121*
C300.2471 (7)0.3001 (6)0.0513 (8)0.129 (5)
H300.26880.32650.02680.155*
C310.2839 (6)0.2582 (6)0.0601 (8)0.115 (4)
H310.33000.25400.03870.138*
C320.2509 (6)0.2223 (5)0.1016 (9)0.119 (4)
H320.27580.19380.11270.143*
C330.1797 (5)0.2284 (4)0.1272 (7)0.092 (3)
H330.15680.20270.15230.110*
C340.4996 (4)0.1673 (3)1.0647 (5)0.054 (2)
C350.5200 (4)0.0812 (3)1.0812 (5)0.055 (2)
H350.53990.08181.03060.067*
C360.4930 (4)0.1229 (3)1.1114 (5)0.0484 (19)
C370.4582 (4)0.1215 (3)1.1865 (5)0.061 (2)
C380.4557 (4)0.0791 (3)1.2274 (5)0.070 (2)
H380.43260.07841.27630.084*
C390.4867 (4)0.0365 (3)1.1983 (6)0.064 (2)
C400.5192 (4)0.0373 (3)1.1226 (5)0.058 (2)
C410.5496 (5)−0.0055 (3)1.0939 (6)0.082 (3)
H410.5707−0.00551.04400.098*
C420.5493 (6)−0.0475 (4)1.1369 (7)0.092 (3)
H420.5699−0.07551.11690.111*
C430.5171 (5)−0.0469 (4)1.2118 (7)0.090 (3)
H430.5174−0.07491.24220.108*
C440.4865 (5)−0.0077 (4)1.2403 (6)0.078 (3)
H440.4640−0.00911.28950.094*
C450.4684 (4)0.2890 (3)1.0809 (6)0.063 (2)
H450.44890.28961.13170.076*
C460.4745 (4)0.3336 (3)1.0384 (6)0.067 (2)
C470.5048 (4)0.3392 (3)0.9619 (6)0.063 (2)
C480.5051 (5)0.3862 (3)0.9287 (6)0.073 (3)
H480.52420.39080.87830.088*
C490.4779 (5)0.4253 (4)0.9690 (8)0.091 (3)
H490.47900.45580.94600.109*
C500.4489 (6)0.4195 (4)1.0435 (8)0.097 (3)
H500.42990.44581.07060.116*
C510.4481 (5)0.3749 (4)1.0773 (7)0.083 (3)
H510.42930.37161.12810.100*
C520.5885 (5)0.2427 (4)0.7825 (6)0.078 (3)
H520.57900.27520.79150.094*
C530.6153 (5)0.2296 (4)0.7085 (6)0.088 (3)
H530.62330.25230.66880.106*
C540.6290 (5)0.1823 (5)0.6973 (6)0.091 (3)
H540.64720.17220.64880.110*
C550.6170 (6)0.1492 (4)0.7547 (7)0.096 (3)
H550.62560.11650.74620.115*
C560.5914 (5)0.1658 (4)0.8263 (6)0.082 (3)
H560.58460.14370.86710.098*
C570.3986 (5)0.2548 (4)0.8448 (7)0.096 (4)
H570.42190.28440.84010.115*
C580.3372 (6)0.2479 (5)0.8014 (8)0.124 (5)
H580.31960.27280.76960.148*
C590.3017 (6)0.2060 (5)0.8038 (8)0.117 (4)
H590.26050.20020.77290.141*
C600.3292 (6)0.1728 (4)0.8534 (9)0.131 (5)
H600.30650.14300.85840.158*
C610.3906 (5)0.1828 (4)0.8968 (7)0.097 (4)
H610.40730.15940.93190.117*
C620.6794 (5)0.2033 (4)1.0215 (6)0.089 (3)
H620.65580.17371.02400.106*
C630.7500 (6)0.2063 (5)1.0498 (8)0.116 (4)
H630.77330.17931.07070.140*
C640.7839 (6)0.2490 (5)1.0464 (7)0.106 (4)
H640.83160.25201.06460.127*
C650.7491 (6)0.2868 (5)1.0172 (7)0.105 (4)
H650.77140.31691.01450.126*
C660.6793 (5)0.2802 (4)0.9910 (6)0.083 (3)
H660.65500.30710.97120.100*
C670.7641 (17)0.4404 (9)0.1201 (17)0.212 (10)
H670.79110.44200.16690.254*
C680.6901 (16)0.4471 (9)0.1272 (14)0.195 (9)
H680.66910.45650.17480.234*
C690.6528 (12)0.4401 (9)0.066 (2)0.206 (9)
H690.60220.44000.06830.247*
C700.6870 (17)0.4326 (9)−0.0024 (16)0.224 (10)
H700.66100.4295−0.04970.269*
C710.7634 (17)0.4294 (9)−0.0012 (18)0.217 (10)
H710.78860.4245−0.04820.260*
C720.2769 (9)0.4078 (5)0.5960 (12)0.140 (5)
H720.30470.39530.63750.168*
C730.2048 (9)0.4113 (6)0.6034 (11)0.142 (5)
H730.18140.40060.64880.170*
C740.1660 (9)0.4315 (6)0.5412 (13)0.145 (5)
H740.11560.43380.54460.174*
C750.1995 (8)0.4475 (5)0.4766 (9)0.119 (4)
H750.17340.46250.43610.143*
C760.2728 (9)0.4416 (6)0.4712 (10)0.133 (5)
H760.29710.45160.42580.160*
C770.3016 (12)0.4440 (11)0.2009 (17)0.247 (13)
H770.35030.43510.20420.296*
C780.2691 (15)0.4681 (11)0.2635 (17)0.255 (13)
H780.29600.47540.30880.307*
C790.1962 (16)0.4814 (10)0.2585 (17)0.255 (12)
H790.17440.49750.30050.306*
C800.1560 (13)0.4706 (11)0.191 (2)0.253 (12)
H800.10730.47950.18740.303*
C810.1885 (15)0.4464 (12)0.1282 (17)0.273 (14)
H810.16160.43910.08290.328*
C820.2274 (11)0.6356 (6)0.2040 (11)0.135 (6)
H820.20420.64940.16030.162*
C830.2988 (12)0.6346 (6)0.2042 (11)0.163 (6)
H830.32480.64780.16230.196*
C840.3352 (9)0.6133 (7)0.2683 (14)0.168 (7)
H840.38570.61160.27110.202*
C850.2907 (12)0.5950 (7)0.3276 (11)0.179 (7)
H850.31010.58060.37290.215*
C860.2179 (12)0.5990 (8)0.3164 (13)0.170 (7)
H860.18730.58590.35450.204*
C870.2369 (8)0.5786 (5)0.5488 (10)0.134 (5)
H870.21350.59650.50970.161*
C880.3095 (9)0.5721 (6)0.5420 (10)0.140 (5)
H880.33580.58490.50000.169*
C890.3403 (7)0.5468 (5)0.5982 (10)0.114 (4)
H890.39040.54210.59710.137*
C900.3027 (8)0.5277 (5)0.6559 (9)0.129 (5)
H900.32610.50960.69490.155*
C910.2286 (8)0.5344 (6)0.6591 (9)0.130 (5)
H910.20120.51970.69860.156*
C920.2952 (11)0.4024 (9)0.8709 (16)0.200 (9)
H920.34360.41230.86930.240*
C930.2681 (13)0.3713 (8)0.8133 (14)0.183 (8)
H930.29840.36030.77310.220*
C940.1959 (14)0.3566 (6)0.8156 (12)0.159 (6)
H940.17770.33580.77700.191*
C950.1507 (11)0.3731 (9)0.8756 (17)0.177 (8)
H950.10240.36320.87720.213*
C960.1778 (14)0.4042 (9)0.9331 (15)0.189 (8)
H960.14760.41530.97330.227*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.0510 (6)0.0552 (6)0.0488 (7)−0.0001 (4)−0.0095 (5)−0.0051 (5)
Ni20.0517 (6)0.0611 (7)0.0528 (7)0.0015 (5)0.0007 (5)−0.0008 (5)
O10.059 (3)0.054 (3)0.055 (4)0.005 (2)−0.015 (3)−0.008 (3)
O20.115 (5)0.064 (4)0.076 (5)−0.016 (3)−0.041 (4)−0.006 (4)
O30.063 (3)0.056 (3)0.051 (4)−0.006 (2)−0.012 (3)−0.009 (3)
O40.056 (3)0.066 (4)0.046 (4)0.006 (2)0.007 (3)−0.001 (3)
O50.120 (5)0.079 (5)0.076 (5)−0.003 (4)0.035 (4)−0.010 (4)
O60.058 (3)0.059 (4)0.075 (4)−0.003 (3)0.000 (3)−0.001 (3)
N10.051 (4)0.059 (4)0.049 (4)−0.004 (3)−0.007 (3)0.001 (4)
N20.045 (4)0.053 (4)0.056 (5)−0.001 (3)−0.001 (3)−0.005 (3)
N30.059 (4)0.057 (4)0.054 (5)0.001 (3)−0.011 (3)−0.009 (4)
N40.055 (4)0.059 (4)0.058 (5)0.004 (3)−0.003 (3)−0.001 (4)
N50.052 (4)0.076 (5)0.066 (5)0.000 (4)−0.010 (4)−0.015 (4)
N60.058 (4)0.066 (5)0.058 (5)−0.002 (3)0.005 (3)−0.005 (4)
N70.052 (4)0.055 (4)0.068 (5)−0.002 (3)−0.004 (3)−0.003 (4)
N80.059 (4)0.066 (5)0.055 (5)−0.006 (3)0.004 (3)0.014 (4)
N90.051 (4)0.065 (5)0.064 (5)−0.001 (3)−0.007 (3)0.008 (4)
N100.053 (4)0.078 (5)0.065 (5)0.001 (4)0.002 (4)−0.004 (4)
N110.137 (14)0.34 (2)0.117 (15)0.019 (13)0.015 (13)−0.002 (17)
N120.076 (8)0.149 (10)0.161 (13)0.016 (7)0.000 (8)−0.004 (9)
N130.164 (18)0.45 (3)0.26 (3)0.066 (19)−0.030 (18)−0.10 (2)
N140.085 (9)0.220 (16)0.134 (14)0.020 (9)−0.010 (9)−0.029 (12)
N150.077 (7)0.174 (11)0.113 (10)0.016 (7)0.004 (7)0.023 (8)
N160.190 (19)0.254 (19)0.22 (2)−0.047 (15)0.037 (15)−0.054 (15)
C10.043 (4)0.052 (5)0.058 (6)−0.001 (3)−0.005 (4)−0.014 (4)
C20.055 (5)0.054 (5)0.056 (6)−0.001 (4)−0.003 (4)−0.003 (4)
C30.046 (4)0.050 (5)0.060 (6)0.003 (4)0.003 (4)−0.010 (4)
C40.057 (5)0.061 (6)0.070 (7)−0.008 (4)−0.006 (5)0.000 (5)
C50.071 (6)0.061 (6)0.085 (8)−0.015 (4)−0.009 (5)−0.011 (5)
C60.058 (5)0.056 (5)0.079 (7)−0.012 (4)0.008 (5)−0.002 (5)
C70.053 (5)0.056 (5)0.070 (6)−0.001 (4)0.014 (4)0.000 (5)
C80.071 (6)0.069 (6)0.084 (8)0.005 (5)−0.003 (5)0.001 (6)
C90.083 (7)0.068 (7)0.097 (9)0.006 (5)0.002 (6)0.024 (6)
C100.086 (7)0.059 (6)0.114 (10)−0.013 (5)0.003 (6)0.002 (7)
C110.078 (7)0.062 (6)0.094 (8)−0.011 (5)−0.006 (6)−0.005 (6)
C120.049 (5)0.064 (5)0.044 (5)−0.005 (4)−0.007 (4)−0.006 (4)
C130.048 (5)0.058 (5)0.054 (6)0.000 (4)−0.007 (4)0.001 (4)
C140.051 (5)0.063 (6)0.054 (6)0.004 (4)−0.003 (4)0.000 (5)
C150.073 (6)0.060 (6)0.068 (7)0.000 (4)−0.013 (5)−0.001 (5)
C160.082 (7)0.062 (6)0.083 (8)0.002 (5)−0.009 (6)0.009 (6)
C170.090 (7)0.073 (7)0.076 (8)0.000 (5)−0.014 (6)0.012 (6)
C180.071 (6)0.070 (6)0.057 (6)−0.005 (4)−0.016 (4)−0.002 (5)
C190.107 (8)0.071 (7)0.077 (8)0.018 (5)−0.038 (6)−0.015 (6)
C200.133 (10)0.092 (8)0.088 (9)0.020 (7)−0.052 (8)−0.027 (7)
C210.109 (9)0.119 (10)0.071 (8)0.009 (7)−0.026 (6)−0.026 (8)
C220.111 (9)0.113 (10)0.060 (8)−0.008 (7)−0.030 (6)0.012 (7)
C230.098 (8)0.084 (7)0.069 (8)−0.019 (5)−0.023 (6)0.003 (6)
C240.087 (7)0.080 (7)0.093 (8)0.013 (5)0.019 (6)0.015 (6)
C250.081 (8)0.126 (10)0.112 (10)0.011 (7)0.031 (7)0.032 (8)
C260.093 (9)0.138 (12)0.127 (12)0.030 (8)0.039 (8)0.013 (9)
C270.106 (10)0.118 (10)0.157 (13)0.042 (8)0.043 (9)0.007 (9)
C280.081 (7)0.085 (8)0.118 (10)0.015 (6)0.023 (6)0.003 (7)
C290.066 (7)0.116 (9)0.121 (10)−0.002 (6)0.006 (6)0.006 (8)
C300.074 (9)0.170 (14)0.144 (12)−0.006 (8)0.029 (8)0.011 (10)
C310.065 (8)0.153 (13)0.127 (12)0.001 (8)0.018 (7)−0.028 (10)
C320.070 (8)0.135 (11)0.152 (13)0.020 (7)−0.002 (8)−0.042 (10)
C330.064 (7)0.091 (8)0.119 (10)0.002 (5)−0.007 (6)−0.008 (6)
C340.040 (4)0.063 (5)0.057 (6)−0.004 (4)−0.005 (4)0.001 (5)
C350.052 (5)0.068 (6)0.046 (5)−0.003 (4)−0.003 (4)0.002 (4)
C360.039 (4)0.062 (5)0.045 (5)−0.009 (3)0.000 (3)0.002 (4)
C370.054 (5)0.072 (6)0.057 (6)−0.009 (4)0.008 (4)−0.007 (5)
C380.066 (6)0.086 (7)0.057 (6)−0.017 (5)0.005 (4)0.006 (5)
C390.053 (5)0.072 (6)0.066 (7)−0.014 (4)−0.010 (4)0.009 (5)
C400.049 (5)0.068 (6)0.057 (6)−0.004 (4)−0.007 (4)0.000 (5)
C410.080 (7)0.077 (7)0.088 (8)0.003 (5)0.004 (5)0.014 (6)
C420.096 (8)0.084 (8)0.097 (9)0.010 (6)−0.005 (7)0.017 (7)
C430.088 (8)0.078 (8)0.103 (10)−0.012 (6)−0.017 (7)0.026 (7)
C440.077 (7)0.085 (7)0.073 (7)−0.018 (5)−0.005 (5)0.012 (6)
C450.058 (5)0.057 (5)0.075 (7)0.001 (4)−0.001 (4)−0.013 (5)
C460.057 (5)0.063 (6)0.081 (7)0.003 (4)−0.005 (5)−0.017 (5)
C470.052 (5)0.066 (6)0.072 (7)0.001 (4)−0.006 (4)0.003 (5)
C480.082 (6)0.060 (6)0.078 (7)0.000 (5)−0.008 (5)−0.002 (5)
C490.096 (8)0.071 (7)0.106 (10)0.007 (6)−0.001 (7)0.004 (7)
C500.096 (8)0.074 (8)0.120 (11)0.017 (6)−0.003 (7)−0.018 (7)
C510.081 (7)0.069 (7)0.101 (9)0.006 (5)0.001 (6)−0.012 (6)
C520.073 (6)0.088 (7)0.074 (8)0.002 (5)0.003 (5)0.008 (6)
C530.096 (8)0.107 (9)0.062 (7)0.000 (6)0.016 (6)0.019 (6)
C540.097 (8)0.115 (9)0.061 (7)−0.004 (7)0.015 (6)−0.007 (7)
C550.112 (8)0.097 (8)0.079 (8)−0.009 (6)0.035 (6)−0.008 (7)
C560.090 (7)0.081 (7)0.075 (8)−0.008 (5)0.014 (5)0.007 (6)
C570.077 (7)0.100 (8)0.111 (9)−0.029 (6)−0.033 (6)0.048 (7)
C580.099 (9)0.116 (10)0.155 (13)−0.031 (7)−0.063 (8)0.058 (9)
C590.098 (9)0.115 (10)0.137 (12)−0.038 (7)−0.053 (8)0.047 (8)
C600.096 (9)0.110 (10)0.187 (14)−0.039 (7)−0.066 (9)0.036 (10)
C610.084 (7)0.075 (7)0.131 (10)−0.006 (6)−0.046 (7)0.021 (7)
C620.056 (6)0.103 (8)0.106 (9)−0.001 (5)−0.008 (5)0.010 (7)
C630.070 (8)0.141 (12)0.137 (12)0.005 (7)−0.027 (7)0.022 (9)
C640.051 (7)0.152 (12)0.113 (10)−0.010 (7)−0.012 (6)0.003 (9)
C650.063 (7)0.130 (10)0.123 (11)−0.026 (7)−0.006 (6)−0.003 (8)
C660.065 (7)0.088 (7)0.097 (8)−0.004 (5)−0.004 (5)0.000 (6)
C670.16 (2)0.34 (3)0.13 (2)0.01 (2)−0.029 (16)0.01 (2)
C680.15 (2)0.33 (3)0.107 (16)−0.019 (19)0.009 (14)−0.004 (17)
C690.156 (19)0.30 (3)0.16 (2)−0.015 (17)0.00 (2)0.00 (2)
C700.17 (2)0.35 (3)0.15 (2)−0.02 (2)−0.016 (17)−0.05 (2)
C710.15 (2)0.35 (3)0.15 (2)0.00 (2)0.033 (17)−0.03 (2)
C720.101 (12)0.154 (13)0.165 (17)0.011 (9)−0.021 (11)0.030 (11)
C730.107 (12)0.175 (15)0.144 (15)−0.008 (10)0.016 (10)0.034 (11)
C740.106 (12)0.169 (15)0.160 (17)0.004 (10)0.002 (12)−0.012 (13)
C750.097 (11)0.152 (12)0.108 (12)−0.002 (9)−0.019 (8)−0.017 (9)
C760.098 (12)0.169 (14)0.132 (14)−0.022 (10)0.010 (10)−0.032 (11)
C770.148 (18)0.42 (4)0.17 (2)0.09 (2)−0.054 (17)−0.09 (2)
C780.16 (2)0.38 (4)0.22 (3)0.08 (2)−0.046 (19)−0.06 (2)
C790.17 (2)0.38 (4)0.22 (3)0.02 (2)−0.03 (2)−0.05 (2)
C800.16 (2)0.38 (4)0.22 (3)0.02 (2)−0.04 (2)−0.08 (3)
C810.15 (2)0.44 (4)0.22 (3)0.04 (2)−0.03 (2)−0.10 (3)
C820.105 (13)0.174 (15)0.126 (15)0.027 (11)−0.051 (11)0.011 (11)
C830.154 (17)0.212 (18)0.123 (15)−0.025 (13)−0.013 (13)0.029 (12)
C840.109 (13)0.24 (2)0.154 (18)−0.004 (12)−0.025 (13)−0.002 (15)
C850.139 (17)0.27 (2)0.129 (16)0.013 (15)−0.014 (13)0.016 (15)
C860.109 (15)0.26 (2)0.137 (17)−0.015 (14)0.013 (12)−0.004 (15)
C870.097 (11)0.160 (13)0.145 (14)0.025 (9)−0.014 (10)0.047 (11)
C880.105 (12)0.175 (14)0.142 (14)−0.010 (10)0.000 (10)0.033 (11)
C890.068 (8)0.151 (12)0.124 (12)−0.002 (8)−0.016 (8)0.008 (10)
C900.097 (11)0.174 (14)0.117 (12)0.013 (9)−0.013 (9)0.020 (10)
C910.097 (11)0.180 (14)0.113 (12)0.002 (9)0.014 (8)0.016 (11)
C920.152 (18)0.26 (3)0.19 (2)−0.039 (17)0.035 (17)−0.036 (19)
C930.17 (2)0.21 (2)0.17 (2)−0.020 (14)0.062 (15)−0.028 (15)
C940.164 (18)0.168 (15)0.143 (16)−0.023 (14)−0.021 (13)−0.048 (12)
C950.130 (16)0.21 (2)0.19 (2)−0.009 (15)−0.008 (17)0.034 (18)
C960.14 (2)0.23 (2)0.19 (2)0.004 (15)0.034 (16)−0.011 (18)

Geometric parameters (Å, °)

Ni1—O12.050 (5)C35—C401.404 (10)
Ni1—O31.998 (5)C35—H350.9300
Ni1—N21.989 (7)C36—C371.424 (11)
Ni1—N32.077 (6)C37—C381.364 (11)
Ni1—N42.192 (6)C38—C391.403 (12)
Ni1—N52.173 (7)C38—H380.9300
Ni2—O42.061 (5)C39—C401.412 (11)
Ni2—O61.993 (5)C39—C441.416 (12)
Ni2—N71.983 (7)C40—C411.399 (11)
Ni2—N82.067 (7)C41—C421.371 (12)
Ni2—N92.156 (6)C41—H410.9300
Ni2—N102.180 (7)C42—C431.397 (14)
O1—C11.280 (9)C42—H420.9300
O2—C41.346 (10)C43—C441.315 (13)
O2—H20.8200C43—H430.9300
O3—C141.302 (9)C44—H440.9300
O4—C341.291 (9)C45—C461.433 (12)
O5—C371.341 (9)C45—H450.9300
O5—H50.8200C46—C511.407 (12)
O6—C471.300 (10)C46—C471.418 (12)
N1—C11.322 (10)C47—C481.418 (11)
N1—N21.400 (8)C48—C491.375 (12)
N2—C121.266 (9)C48—H480.9300
N3—C191.310 (10)C49—C501.377 (14)
N3—C231.333 (11)C49—H490.9300
N4—C241.298 (10)C50—C511.360 (13)
N4—C281.303 (10)C50—H500.9300
N5—C331.312 (11)C51—H510.9300
N5—C291.313 (12)C52—C531.392 (13)
N6—C341.340 (9)C52—H520.9300
N6—N71.397 (9)C53—C541.348 (13)
N7—C451.293 (9)C53—H530.9300
N8—C521.312 (11)C54—C551.354 (13)
N8—C561.339 (10)C54—H540.9300
N9—C571.293 (10)C55—C561.378 (13)
N9—C611.314 (10)C55—H550.9300
N10—C661.290 (10)C56—H560.9300
N10—C621.309 (11)C57—C581.352 (13)
N11—C671.17 (2)C57—H570.9300
N11—C711.23 (2)C58—C591.334 (14)
N12—C761.302 (17)C58—H580.9300
N12—C721.333 (17)C59—C601.340 (14)
N13—C771.39 (2)C59—H590.9300
N13—C811.39 (2)C60—C611.369 (13)
N14—C821.223 (18)C60—H600.9300
N14—C861.27 (2)C61—H610.9300
N15—C871.290 (15)C62—C631.381 (13)
N15—C911.307 (15)C62—H620.9300
N16—C921.39 (2)C63—C641.339 (14)
N16—C961.39 (2)C63—H630.9300
C1—C31.497 (10)C64—C651.322 (14)
C2—C31.367 (10)C64—H640.9300
C2—C71.398 (10)C65—C661.367 (13)
C2—H2A0.9300C65—H650.9300
C3—C41.425 (11)C66—H660.9300
C4—C51.381 (11)C67—C681.38 (2)
C5—C61.409 (12)C67—H670.9300
C5—H5A0.9300C68—C691.25 (2)
C6—C111.401 (11)C68—H680.9300
C6—C71.414 (12)C69—C701.34 (2)
C7—C81.411 (12)C69—H690.9300
C8—C91.363 (11)C70—C711.41 (3)
C8—H80.9300C70—H700.9300
C9—C101.412 (13)C71—H710.9300
C9—H90.9300C72—C731.335 (17)
C10—C111.357 (13)C72—H720.9300
C10—H100.9300C73—C741.381 (19)
C11—H110.9300C73—H730.9300
C12—C131.432 (10)C74—C751.332 (18)
C12—H120.9300C74—H740.9300
C13—C141.402 (11)C75—C761.360 (17)
C13—C181.403 (11)C75—H750.9300
C14—C151.414 (11)C76—H760.9300
C15—C161.354 (12)C77—C781.39 (3)
C15—H150.9300C77—H770.9300
C16—C171.378 (12)C78—C791.39 (2)
C16—H160.9300C78—H780.9300
C17—C181.373 (11)C79—C801.39 (3)
C17—H170.9300C79—H790.9300
C18—H180.9300C80—C811.39 (3)
C19—C201.349 (13)C80—H800.9300
C19—H190.9300C81—H810.9300
C20—C211.357 (14)C82—C831.312 (19)
C20—H200.9300C82—H820.9300
C21—C221.368 (13)C83—C841.40 (2)
C21—H210.9300C83—H830.9300
C22—C231.343 (13)C84—C851.39 (2)
C22—H220.9300C84—H840.9300
C23—H230.9300C85—C861.35 (2)
C24—C251.382 (13)C85—H850.9300
C24—H240.9300C86—H860.9300
C25—C261.323 (15)C87—C881.351 (16)
C25—H250.9300C87—H870.9300
C26—C271.356 (15)C88—C891.305 (17)
C26—H260.9300C88—H880.9300
C27—C281.404 (14)C89—C901.310 (16)
C27—H270.9300C89—H890.9300
C28—H280.9300C90—C911.374 (16)
C29—C301.377 (14)C90—H900.9300
C29—H290.9300C91—H910.9300
C30—C311.354 (15)C92—C931.39 (2)
C30—H300.9300C92—H920.9300
C31—C321.361 (16)C93—C941.39 (2)
C31—H310.9300C93—H930.9300
C32—C331.391 (14)C94—C951.39 (2)
C32—H320.9300C94—H940.9300
C33—H330.9300C95—C961.39 (2)
C34—C361.465 (10)C95—H950.9300
C35—C361.357 (10)C96—H960.9300
N2—Ni1—O390.5 (2)C38—C37—C36119.3 (8)
N2—Ni1—O179.4 (2)C37—C38—C39122.3 (8)
O3—Ni1—O1170.0 (2)C37—C38—H38118.8
N2—Ni1—N3174.6 (3)C39—C38—H38118.8
O3—Ni1—N394.8 (2)C38—C39—C40118.5 (8)
O1—Ni1—N395.3 (2)C38—C39—C44123.5 (9)
N2—Ni1—N593.5 (2)C40—C39—C44118.0 (9)
O3—Ni1—N590.6 (3)C41—C40—C35123.9 (8)
O1—Ni1—N590.1 (3)C41—C40—C39118.1 (8)
N3—Ni1—N587.3 (2)C35—C40—C39118.0 (8)
N2—Ni1—N492.5 (2)C42—C41—C40122.3 (10)
O3—Ni1—N490.9 (2)C42—C41—H41118.9
O1—Ni1—N489.4 (2)C40—C41—H41118.9
N3—Ni1—N486.7 (2)C41—C42—C43118.1 (10)
N5—Ni1—N4173.9 (3)C41—C42—H42120.9
N7—Ni2—O690.4 (3)C43—C42—H42120.9
N7—Ni2—O479.5 (2)C44—C43—C42121.6 (10)
O6—Ni2—O4169.8 (2)C44—C43—H43119.2
N7—Ni2—N8174.4 (3)C42—C43—H43119.2
O6—Ni2—N895.1 (3)C43—C44—C39121.9 (10)
O4—Ni2—N895.1 (2)C43—C44—H44119.1
N7—Ni2—N992.4 (3)C39—C44—H44119.1
O6—Ni2—N991.7 (2)N7—C45—C46123.1 (8)
O4—Ni2—N989.7 (2)N7—C45—H45118.4
N8—Ni2—N986.1 (3)C46—C45—H45118.4
N7—Ni2—N1093.9 (3)C51—C46—C47118.3 (9)
O6—Ni2—N1090.4 (3)C51—C46—C45116.1 (9)
O4—Ni2—N1089.3 (3)C47—C46—C45125.6 (8)
N8—Ni2—N1087.3 (3)O6—C47—C46123.9 (8)
N9—Ni2—N10173.3 (3)O6—C47—C48118.5 (9)
C1—O1—Ni1109.8 (5)C46—C47—C48117.6 (9)
C4—O2—H2109.5C49—C48—C47121.8 (10)
C14—O3—Ni1126.9 (5)C49—C48—H48119.1
C34—O4—Ni2109.7 (5)C47—C48—H48119.1
C37—O5—H5109.5C48—C49—C50120.2 (10)
C47—O6—Ni2127.9 (6)C48—C49—H49119.9
C1—N1—N2111.3 (6)C50—C49—H49119.9
C12—N2—N1117.4 (7)C51—C50—C49119.6 (10)
C12—N2—Ni1128.3 (6)C51—C50—H50120.2
N1—N2—Ni1114.2 (5)C49—C50—H50120.2
C19—N3—C23117.4 (8)C50—C51—C46122.6 (10)
C19—N3—Ni1121.0 (6)C50—C51—H51118.7
C23—N3—Ni1121.6 (6)C46—C51—H51118.7
C24—N4—C28116.3 (8)N8—C52—C53124.3 (10)
C24—N4—Ni1123.0 (6)N8—C52—H52117.8
C28—N4—Ni1120.5 (6)C53—C52—H52117.8
C33—N5—C29116.0 (9)C54—C53—C52116.4 (10)
C33—N5—Ni1121.7 (7)C54—C53—H53121.8
C29—N5—Ni1122.2 (7)C52—C53—H53121.8
C34—N6—N7111.2 (6)C53—C54—C55122.0 (10)
C45—N7—N6115.9 (7)C53—C54—H54119.0
C45—N7—Ni2129.0 (6)C55—C54—H54119.0
N6—N7—Ni2115.1 (5)C54—C55—C56117.2 (10)
C52—N8—C56116.7 (8)C54—C55—H55121.4
C52—N8—Ni2122.2 (7)C56—C55—H55121.4
C56—N8—Ni2121.1 (6)N8—C56—C55123.3 (9)
C57—N9—C61113.8 (8)N8—C56—H56118.3
C57—N9—Ni2122.4 (6)C55—C56—H56118.3
C61—N9—Ni2123.4 (6)N9—C57—C58125.2 (10)
C66—N10—C62115.0 (8)N9—C57—H57117.4
C66—N10—Ni2122.5 (7)C58—C57—H57117.4
C62—N10—Ni2122.5 (7)C59—C58—C57120.8 (11)
C67—N11—C71118 (3)C59—C58—H58119.6
C76—N12—C72122.1 (14)C57—C58—H58119.6
C77—N13—C81120 (2)C58—C59—C60115.8 (10)
C82—N14—C86120.0 (18)C58—C59—H59122.1
C87—N15—C91118.6 (12)C60—C59—H59122.1
C92—N16—C96120 (2)C59—C60—C61120.0 (11)
O1—C1—N1125.2 (7)C59—C60—H60120.0
O1—C1—C3118.6 (8)C61—C60—H60120.0
N1—C1—C3116.1 (7)N9—C61—C60124.3 (10)
C3—C2—C7122.1 (8)N9—C61—H61117.8
C3—C2—H2A119.0C60—C61—H61117.8
C7—C2—H2A119.0N10—C62—C63123.5 (10)
C2—C3—C4119.0 (7)N10—C62—H62118.2
C2—C3—C1118.9 (7)C63—C62—H62118.2
C4—C3—C1122.1 (8)C64—C63—C62118.2 (11)
O2—C4—C5118.5 (8)C64—C63—H63120.9
O2—C4—C3121.6 (7)C62—C63—H63120.9
C5—C4—C3119.9 (9)C65—C64—C63119.6 (11)
C4—C5—C6121.2 (8)C65—C64—H64120.2
C4—C5—H5A119.4C63—C64—H64120.2
C6—C5—H5A119.4C64—C65—C66117.6 (11)
C11—C6—C5121.7 (9)C64—C65—H65121.2
C11—C6—C7119.7 (9)C66—C65—H65121.2
C5—C6—C7118.5 (8)N10—C66—C65126.0 (10)
C2—C7—C8122.3 (9)N10—C66—H66117.0
C2—C7—C6119.4 (8)C65—C66—H66117.0
C8—C7—C6118.3 (8)N11—C67—C68128 (2)
C9—C8—C7121.2 (9)N11—C67—H67116.2
C9—C8—H8119.4C68—C67—H67116.2
C7—C8—H8119.4C69—C68—C67116 (2)
C8—C9—C10119.5 (10)C69—C68—H68121.8
C8—C9—H9120.2C67—C68—H68121.8
C10—C9—H9120.2C68—C69—C70119 (3)
C11—C10—C9120.7 (9)C68—C69—H69120.7
C11—C10—H10119.6C70—C69—H69120.7
C9—C10—H10119.6C69—C70—C71118 (2)
C10—C11—C6120.5 (10)C69—C70—H70120.9
C10—C11—H11119.8C71—C70—H70120.9
C6—C11—H11119.8N11—C71—C70120 (2)
N2—C12—C13124.4 (8)N11—C71—H71119.9
N2—C12—H12117.8C70—C71—H71119.9
C13—C12—H12117.8N12—C72—C73120.2 (15)
C14—C13—C18118.7 (8)N12—C72—H72119.9
C14—C13—C12125.0 (8)C73—C72—H72119.9
C18—C13—C12116.2 (7)C72—C73—C74117.8 (16)
O3—C14—C13124.7 (7)C72—C73—H73121.1
O3—C14—C15118.2 (8)C74—C73—H73121.1
C13—C14—C15117.1 (8)C75—C74—C73121.1 (16)
C16—C15—C14122.2 (9)C75—C74—H74119.5
C16—C15—H15118.9C73—C74—H74119.5
C14—C15—H15118.9C74—C75—C76118.5 (15)
C15—C16—C17121.4 (9)C74—C75—H75120.7
C15—C16—H16119.3C76—C75—H75120.7
C17—C16—H16119.3N12—C76—C75120.2 (15)
C18—C17—C16117.6 (9)N12—C76—H76119.9
C18—C17—H17121.2C75—C76—H76119.9
C16—C17—H17121.2C78—C77—N13120 (2)
C17—C18—C13123.0 (8)C78—C77—H77120.0
C17—C18—H18118.5N13—C77—H77120.0
C13—C18—H18118.5C77—C78—C79120 (2)
N3—C19—C20123.5 (10)C77—C78—H78120.0
N3—C19—H19118.3C79—C78—H78120.0
C20—C19—H19118.3C80—C79—C78120 (3)
C19—C20—C21119.0 (11)C80—C79—H79120.0
C19—C20—H20120.5C78—C79—H79120.0
C21—C20—H20120.5C81—C80—C79120 (3)
C20—C21—C22118.2 (10)C81—C80—H80120.0
C20—C21—H21120.9C79—C80—H80120.0
C22—C21—H21120.9C80—C81—N13120 (2)
C23—C22—C21119.3 (10)C80—C81—H81120.0
C23—C22—H22120.4N13—C81—H81120.0
C21—C22—H22120.4N14—C82—C83124.8 (17)
N3—C23—C22122.6 (10)N14—C82—H82117.6
N3—C23—H23118.7C83—C82—H82117.6
C22—C23—H23118.7C82—C83—C84119.0 (17)
N4—C24—C25124.3 (10)C82—C83—H83120.5
N4—C24—H24117.9C84—C83—H83120.5
C25—C24—H24117.9C85—C84—C83115.5 (17)
C26—C25—C24119.6 (11)C85—C84—H84122.3
C26—C25—H25120.2C83—C84—H84122.3
C24—C25—H25120.2C86—C85—C84116.9 (18)
C25—C26—C27118.0 (11)C86—C85—H85121.5
C25—C26—H26121.0C84—C85—H85121.5
C27—C26—H26121.0N14—C86—C85123.7 (19)
C26—C27—C28118.7 (11)N14—C86—H86118.1
C26—C27—H27120.6C85—C86—H86118.1
C28—C27—H27120.6N15—C87—C88124.9 (13)
N4—C28—C27122.9 (10)N15—C87—H87117.5
N4—C28—H28118.5C88—C87—H87117.5
C27—C28—H28118.5C89—C88—C87115.7 (14)
N5—C29—C30124.7 (11)C89—C88—H88122.2
N5—C29—H29117.6C87—C88—H88122.2
C30—C29—H29117.6C88—C89—C90121.9 (14)
C31—C30—C29118.9 (13)C88—C89—H89119.0
C31—C30—H30120.5C90—C89—H89119.0
C29—C30—H30120.5C89—C90—C91120.1 (14)
C30—C31—C32117.5 (12)C89—C90—H90119.9
C30—C31—H31121.3C91—C90—H90119.9
C32—C31—H31121.3N15—C91—C90118.6 (13)
C31—C32—C33119.5 (12)N15—C91—H91120.7
C31—C32—H32120.2C90—C91—H91120.7
C33—C32—H32120.2N16—C92—C93120 (2)
N5—C33—C32123.2 (11)N16—C92—H92120.0
N5—C33—H33118.4C93—C92—H92120.0
C32—C33—H33118.4C92—C93—C94120.0 (18)
O4—C34—N6124.5 (7)C92—C93—H93120.0
O4—C34—C36119.5 (7)C94—C93—H93120.0
N6—C34—C36116.0 (7)C95—C94—C93119.9 (18)
C36—C35—C40123.1 (8)C95—C94—H94120.0
C36—C35—H35118.4C93—C94—H94120.0
C40—C35—H35118.4C96—C95—C94120 (2)
C35—C36—C37118.6 (7)C96—C95—H95120.0
C35—C36—C34118.8 (7)C94—C95—H95120.0
C37—C36—C34122.6 (7)C95—C96—N16120 (2)
O5—C37—C38119.7 (8)C95—C96—H96120.0
O5—C37—C36121.0 (8)N16—C96—H96120.0

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···N10.821.822.558 (8)148
O5—H5···N60.821.802.533 (9)148

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2364).

References

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  • Kang, W., Sun, S., Li, D., Wang, D. & Dou, J. (2007). Acta Cryst. E63, m2667.
  • Samanta, B., Chakraborty, J., Shit, S., Batten, S. R., Jensen, P., Masuda, J. D. & Mitra, S. (2007). Inorg. Chim. Acta, 360, 2471–2484.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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