metal-organic papers
m2526
Huet al. [Ni(C14H10N2O3)(C5H5N)3]1.5C5H5N doi:10.1107/S1600536805035701 Acta Cryst.(2005). E61, m2526–m2527
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
Tris(pyridine-
j
N
)[salicylaldehyde
(2-hydroxy-benzoyl)hydrazonato-
j
2N
,
O
]nickel(II) pyridine
sesquisolvate
Zong-Qiu Hu,a* Wen-Hui Li,a,b Yu Dingcand Yu Wua
a
Department of Chemistry, Central China Normal University, Wuhan, Hubei 430079, People’s Republic of China,bDepartment of Chemical Engineering, Jingmen Technical College, Jingmen, Hubei 448000, People’s Republic of China, andcDepartment of Chemistry, Xiaogan University, Xiaogan, Hubei 432000, People’s Republic of China
Correspondence e-mail: zqhu@mail.ccnu.edu.cn
Key indicators
Single-crystal X-ray study
T= 293 K
Mean(C–C) = 0.007 A˚ Disorder in solvent or counterion
Rfactor = 0.054
wRfactor = 0.155
Data-to-parameter ratio = 15.7
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2005 International Union of Crystallography Printed in Great Britain – all rights reserved
In the title compound, [Ni(C14H10N2O3)(C5H5N)3]1.5C5H5N, the NiIIion is coordinated by one N and two O atoms from a Schiff base ligand and by the N atoms of three pyridine molecules to form a distorted octahedral geometry.
Comment
Previously we have reported the crystal structure of a salicylaldehyde salicylhydrazone ZnIIpyridine complex (Huet al., 2005). Now we report the crystal structure of the title compound, (I).
The asymmetric unit of (I) contains a [Ni(C14H10N2O3 )-(C5H5N)3] unit, a pyridine molecule at a general position and another pyridine molecule disordered over a crystallographic inversion centre (Fig. 1). The NiIIion is coordinated by one N and two O atoms from a Schiff base ligand, and by three N atoms of three pyridine molecules. This NiN4O2coordination forms a distorted octahedral geometry (Table 1). The crystal packing is stabilized by C—H O hydrogen bonds (Table 2).
Experimental
To a ethanol solution (100 ml) of salicylhydrazine (6 g), one molar equivalent of salicylaldehyde in ethanol (50 ml) was added slowly with continuous stirring and the salicylaldehyde salicylhydrazone was precipitated at once. Salicylaldehyde salicylhydrazone (1 mmol), Ni(OAc)2 (1 mmol), DMF (30 ml), and pyridine (10 ml) were
refluxed for 1 h. The hot solution was filtered and allowed to stand at room temperature for 21 d, and red crystals of compound (I) were obtained.
Crystal data
[Ni(C14H10N2O3)(C5H5N)3]
-1.5C5H5N Mr= 668.90
Monoclinic,P21=n a= 12.5579 (10) A˚
b= 20.3993 (17) A˚
c= 13.2756 (11) A˚ = 93.493 (1)
V= 3394.5 (5) A˚3 Z= 4
Dx= 1.309 Mg m
3
MoKradiation Cell parameters from 6390
reflections = 2.3–24.7 = 0.62 mm1
T= 293 (2) K Block, red
0.400.300.20 mm
Data collection
Bruker SMART CCD area-detector diffractometer
’and!scans
Absorption correction: multi-scan (SADABS; Bruker, 2000)
Tmin= 0.791,Tmax= 0.887
18260 measured reflections
6652 independent reflections 5272 reflections withI> 2(I)
Rint= 0.022
max= 26.0 h=15!15
k=19!25
l=16!15
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.054 wR(F2) = 0.155 S= 1.02 6652 reflections 425 parameters
H-atom parameters constrained
w= 1/[2
(Fo2) + (0.0779P)2
+ 1.8492P]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.001
max= 1.31 e A˚
3
min=0.38 e A˚
[image:2.610.46.295.71.238.2] [image:2.610.314.564.93.205.2]3
Table 1
Selected geometric parameters (A˚ ,).
Ni—O3 1.993 (2) Ni—N2 1.995 (2) Ni—O2 2.0475 (19)
Ni—N3 2.083 (2) Ni—N4 2.160 (3) Ni—N5 2.176 (2)
O3—Ni—N2 91.70 (9) O3—Ni—O2 170.75 (8) N2—Ni—O2 79.10 (9) O3—Ni—N3 96.05 (9) N2—Ni—N3 171.75 (9) O2—Ni—N3 93.19 (9) O3—Ni—N4 89.76 (10) N2—Ni—N4 92.80 (9)
O2—Ni—N4 89.83 (10) N3—Ni—N4 90.08 (10) O3—Ni—N5 90.64 (9) N2—Ni—N5 87.96 (9) O2—Ni—N5 89.90 (9) N3—Ni—N5 89.11 (9) N4—Ni—N5 179.13 (9)
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
O1—H1 N1 0.82 1.82 2.549 (3) 147 C16—H16 O1i
0.93 2.58 3.356 (5) 141 C20—H20 O3 0.93 2.43 3.022 (4) 121 C24—H24 O2 0.93 2.47 3.030 (4) 119 C19—H19 O2 0.93 2.52 3.059 (4) 118
Symmetry code: (i)x1 2;yþ
1 2;zþ
1 2.
Atoms N7, C36 and H36 are disordered across a crystallographic inversion centre and hence the occupancy factor for each disordered component was fixed at 0.50. The H atoms were placed in idealized positions and allowed to ride on their parent atoms, with O—H = 0.82 A˚ , C—H = 0.93 A˚ andUiso(H) = 1.2–1.5Ueq(C/O). The highest
peak in the difference map lies close to the Ni atom (0.82 A˚ ). Data collection:SMART(Bruker, 2000); cell refinement:SAINT
(Bruker, 2000); data reduction:SAINT; program(s) used to solve structure:SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
SHELXTL (Bruker, 1997); software used to prepare material for publication:SHELXTL.
This work is supported by Hubei Education Department (grant No. 20040131).
References
Bruker (1997). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2000).SMART,SAINTandSADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Hu, Z.-Q. Ding, Y. & Zhu, X.-D. (2005).Chin. J. Inorg. Chem.21, 78–82. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
[image:2.610.313.564.255.321.2]Go¨ttingen, Germany.
Figure 1
supporting information
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Acta Cryst. (2005). E61, m2526–m2527
supporting information
Acta Cryst. (2005). E61, m2526–m2527 [https://doi.org/10.1107/S1600536805035701]
Tris(pyridine-κ
N
)[salicylaldehyde
(2-hydroxybenzoyl)hydrazonato-κ
2N
,
O
]nickel(II) pyridine sesquisolvate
Zong-Qiu Hu, Wen-Hui Li, Yu Ding and Yu Wu
Tris(pyridine-kN)[salicylaldehyde (2-hydroxybenzoyl)hydrazonato-k2N,O]nickel(II) pyridine sesquisolvate
Crystal data
[Ni(C14H10N2O3)(C5H5N)3]·1.5C5H5N Mr = 668.90
Monoclinic, P21/n
Hall symbol: -P 2yn
a = 12.5579 (10) Å
b = 20.3993 (17) Å
c = 13.2756 (11) Å
β = 93.493 (1)°
V = 3394.5 (5) Å3 Z = 4
F(000) = 1396
Dx = 1.309 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 6390 reflections
θ = 2.3–24.7°
µ = 0.62 mm−1 T = 293 K Block, red
0.40 × 0.30 × 0.20 mm
Data collection
Bruker SMART CCD area-detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
φ and ω scans
Absorption correction: multi-scan (SADABS; Bruker, 2000)
Tmin = 0.791, Tmax = 0.887
18260 measured reflections 6652 independent reflections 5272 reflections with I > 2σ(I)
Rint = 0.022
θmax = 26.0°, θmin = 1.8° h = −15→15
k = −19→25
l = −16→15
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.054 wR(F2) = 0.155 S = 1.03 6652 reflections 425 parameters 3 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained
w = 1/[σ2(F
o2) + (0.0779P)2 + 1.8492P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 1.31 e Å−3
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)
x y z Uiso*/Ueq Occ. (<1)
Ni 0.65046 (3) 0.230127 (18) 0.50273 (3) 0.05522 (15) N1 0.76084 (19) 0.13964 (11) 0.37957 (17) 0.0576 (6) N2 0.77516 (18) 0.19882 (12) 0.42990 (17) 0.0541 (5) N3 0.50755 (19) 0.25283 (13) 0.56663 (18) 0.0588 (6) N4 0.7114 (2) 0.18844 (14) 0.64428 (19) 0.0682 (7) N5 0.58664 (18) 0.27192 (12) 0.36084 (18) 0.0587 (6) N6 0.8332 (8) 0.8952 (3) 0.6927 (5) 0.196 (3) O1 0.7967 (2) 0.04657 (14) 0.2580 (2) 0.1016 (9)
H1 0.8101 0.0786 0.2939 0.152*
O2 0.59816 (16) 0.13937 (9) 0.45611 (15) 0.0624 (5) O3 0.72353 (16) 0.31435 (10) 0.53899 (15) 0.0648 (5) C1 0.7014 (3) 0.02285 (15) 0.2774 (2) 0.0685 (8) C2 0.6650 (4) −0.03255 (18) 0.2278 (3) 0.0866 (11)
H2 0.7069 −0.0519 0.1806 0.104*
C3 0.5685 (4) −0.06022 (19) 0.2459 (3) 0.1023 (13)
H3 0.5454 −0.0977 0.2112 0.123*
C4 0.5069 (4) −0.0326 (2) 0.3147 (4) 0.1077 (14)
H4 0.4423 −0.0518 0.3286 0.129*
C5 0.5398 (3) 0.02344 (16) 0.3637 (3) 0.0768 (9)
H5 0.4963 0.0422 0.4101 0.092*
C6 0.6357 (2) 0.05295 (14) 0.3463 (2) 0.0602 (7) C7 0.6653 (2) 0.11458 (14) 0.3985 (2) 0.0572 (7) C8 0.8628 (2) 0.22989 (14) 0.4203 (2) 0.0583 (7)
H8 0.9125 0.2104 0.3808 0.070*
C9 0.8911 (2) 0.29200 (17) 0.4651 (2) 0.0647 (8) C10 0.9969 (3) 0.3141 (2) 0.4551 (3) 0.0829 (10)
H10 1.0417 0.2889 0.4173 0.099*
C11 1.0365 (3) 0.3707 (2) 0.4983 (3) 0.0976 (12)
H11 1.1064 0.3837 0.4902 0.117*
C12 0.9690 (4) 0.4084 (2) 0.5551 (3) 0.1004 (13)
H12 0.9940 0.4469 0.5855 0.121*
C13 0.8656 (3) 0.38860 (16) 0.5658 (3) 0.0750 (9)
H13 0.8220 0.4150 0.6030 0.090*
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Acta Cryst. (2005). E61, m2526–m2527
H15 0.5185 0.3474 0.5597 0.090*
C16 0.3787 (3) 0.3293 (2) 0.6161 (3) 0.0873 (11)
H16 0.3596 0.3729 0.6236 0.105*
C17 0.3125 (3) 0.2811 (2) 0.6426 (3) 0.0881 (11)
H17 0.2471 0.2907 0.6685 0.106*
C18 0.3440 (3) 0.2181 (2) 0.6304 (4) 0.1102 (16)
H18 0.3003 0.1836 0.6477 0.132*
C19 0.4421 (3) 0.20568 (19) 0.5920 (4) 0.0945 (13)
H19 0.4627 0.1623 0.5836 0.113*
C20 0.6178 (3) 0.33035 (18) 0.3298 (3) 0.0772 (9)
H20 0.6604 0.3559 0.3742 0.093*
C21 0.5905 (3) 0.3549 (2) 0.2360 (3) 0.0927 (11)
H21 0.6145 0.3960 0.2174 0.111*
C22 0.5281 (3) 0.3188 (3) 0.1704 (3) 0.0963 (13)
H22 0.5086 0.3343 0.1060 0.116*
C23 0.4948 (4) 0.2593 (3) 0.2012 (3) 0.0972 (13)
H23 0.4517 0.2333 0.1581 0.117*
C24 0.5249 (3) 0.23775 (18) 0.2955 (3) 0.0767 (9)
H24 0.5009 0.1969 0.3153 0.092*
C25 0.7137 (3) 0.2240 (2) 0.7277 (3) 0.0895 (11)
H25 0.6869 0.2665 0.7244 0.107*
C26 0.7549 (4) 0.2001 (3) 0.8203 (3) 0.1059 (14)
H26 0.7557 0.2265 0.8775 0.127*
C27 0.7934 (4) 0.1387 (3) 0.8265 (4) 0.1115 (15)
H27 0.8207 0.1219 0.8879 0.134*
C28 0.7918 (4) 0.1013 (2) 0.7409 (4) 0.1045 (13)
H28 0.8182 0.0587 0.7427 0.125*
C29 0.7503 (3) 0.12822 (19) 0.6522 (3) 0.0814 (10)
H29 0.7495 0.1026 0.5942 0.098*
C30 0.7414 (6) 0.9049 (4) 0.6297 (9) 0.196 (4)
H30 0.6746 0.8922 0.6492 0.235*
C31 0.7533 (7) 0.9334 (4) 0.5397 (7) 0.165 (3)
H31 0.6944 0.9397 0.4948 0.198*
C32 0.8454 (8) 0.9516 (4) 0.5163 (5) 0.163 (3)
H32 0.8534 0.9754 0.4574 0.196*
C33 0.9293 (6) 0.9367 (5) 0.5760 (8) 0.191 (4)
H33 0.9965 0.9476 0.5555 0.229*
C34 0.9228 (6) 0.9088 (4) 0.6585 (6) 0.155 (3)
H34 0.9850 0.8976 0.6961 0.186*
N7 0.5798 (5) 0.4869 (2) 0.5722 (4) 0.1244 (15) 0.50 C35 0.4799 (6) 0.4981 (3) 0.5967 (4) 0.1213 (17)
H35 0.4643 0.4972 0.6643 0.146*
C36 0.5798 (5) 0.4869 (2) 0.5722 (4) 0.1244 (15) 0.50
H36 0.6339 0.4779 0.6211 0.149* 0.50
C37 0.5987 (5) 0.4892 (3) 0.4739 (6) 0.1256 (18)
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
supporting information
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Acta Cryst. (2005). E61, m2526–m2527
C35 0.158 (5) 0.116 (4) 0.096 (3) −0.020 (4) 0.048 (4) −0.012 (3) C36 0.140 (4) 0.107 (3) 0.127 (4) 0.000 (3) 0.013 (3) −0.010 (3) C37 0.117 (4) 0.115 (4) 0.150 (5) −0.009 (3) 0.049 (4) −0.029 (4)
Geometric parameters (Å, º)
Ni—O3 1.993 (2) C13—H13 0.93
Ni—N2 1.995 (2) C15—C16 1.369 (5)
Ni—O2 2.0475 (19) C15—H15 0.93
Ni—N3 2.083 (2) C16—C17 1.348 (5)
Ni—N4 2.160 (3) C16—H16 0.93
Ni—N5 2.176 (2) C17—C18 1.358 (6)
N1—C7 1.341 (4) C17—H17 0.93
N1—N2 1.386 (3) C18—C19 1.384 (5)
N2—C8 1.283 (4) C18—H18 0.93
N3—C15 1.316 (4) C19—H19 0.93
N3—C19 1.322 (4) C20—C21 1.367 (5)
N4—C25 1.322 (4) C20—H20 0.93
N4—C29 1.324 (4) C21—C22 1.354 (6)
N5—C24 1.325 (4) C21—H21 0.93
N5—C20 1.328 (4) C22—C23 1.355 (6)
N6—C34 1.270 (9) C22—H22 0.93
N6—C30 1.396 (10) C23—C24 1.359 (5)
O1—C1 1.330 (4) C23—H23 0.93
O1—H1 0.82 C24—H24 0.93
O2—C7 1.277 (3) C25—C26 1.392 (6)
O3—C14 1.309 (4) C25—H25 0.93
C1—C2 1.372 (5) C26—C27 1.344 (7)
C1—C6 1.410 (4) C26—H26 0.93
C2—C3 1.372 (6) C27—C28 1.367 (7)
C2—H2 0.93 C27—H27 0.93
C3—C4 1.354 (6) C28—C29 1.372 (5)
C3—H3 0.93 C28—H28 0.93
C4—C5 1.368 (5) C29—H29 0.93
C4—H4 0.93 C30—C31 1.344 (10)
C5—C6 1.378 (4) C30—H30 0.93
C5—H5 0.93 C31—C32 1.273 (9)
C6—C7 1.472 (4) C31—H31 0.93
C8—C9 1.435 (4) C32—C33 1.315 (9)
C8—H8 0.93 C32—H32 0.93
C9—C10 1.417 (4) C33—C34 1.241 (10)
C9—C14 1.424 (5) C33—H33 0.93
C10—C11 1.370 (5) C34—H34 0.93
C10—H10 0.93 N7—C35 1.335 (7)
C11—C12 1.399 (6) N7—C37 1.342 (7)
C11—H11 0.93 C35—C37i 1.344 (8)
C12—C13 1.375 (5) C35—H35 0.93
C13—C14 1.416 (4) C37—H37 0.93
O3—Ni—N2 91.70 (9) O3—C14—C13 119.2 (3)
O3—Ni—O2 170.75 (8) O3—C14—C9 124.4 (3)
N2—Ni—O2 79.10 (9) C13—C14—C9 116.4 (3)
O3—Ni—N3 96.05 (9) N3—C15—C16 123.8 (3)
N2—Ni—N3 171.75 (9) N3—C15—H15 118.1
O2—Ni—N3 93.19 (9) C16—C15—H15 118.1
O3—Ni—N4 89.76 (10) C17—C16—C15 119.6 (4)
N2—Ni—N4 92.80 (9) C17—C16—H16 120.2
O2—Ni—N4 89.83 (10) C15—C16—H16 120.2
N3—Ni—N4 90.08 (10) C16—C17—C18 118.0 (3)
O3—Ni—N5 90.64 (9) C16—C17—H17 121.0
N2—Ni—N5 87.96 (9) C18—C17—H17 121.0
O2—Ni—N5 89.90 (9) C17—C18—C19 119.3 (4)
N3—Ni—N5 89.11 (9) C17—C18—H18 120.3
N4—Ni—N5 179.13 (9) C19—C18—H18 120.3
C7—N1—N2 109.4 (2) N3—C19—C18 122.8 (4)
C8—N2—N1 118.0 (2) N3—C19—H19 118.6
C8—N2—Ni 126.4 (2) C18—C19—H19 118.6
N1—N2—Ni 115.45 (16) N5—C20—C21 123.3 (3)
C15—N3—C19 116.5 (3) N5—C20—H20 118.4
C15—N3—Ni 122.9 (2) C21—C20—H20 118.4
C19—N3—Ni 120.4 (2) C22—C21—C20 119.4 (4)
C25—N4—C29 116.9 (3) C22—C21—H21 120.3
C25—N4—Ni 120.1 (3) C20—C21—H21 120.3
C29—N4—Ni 123.0 (2) C21—C22—C23 118.0 (4)
C24—N5—C20 116.2 (3) C21—C22—H22 121.0
C24—N5—Ni 122.0 (2) C23—C22—H22 121.0
C20—N5—Ni 121.3 (2) C22—C23—C24 119.7 (4)
C34—N6—C30 118.2 (7) C22—C23—H23 120.2
C1—O1—H1 109.5 C24—C23—H23 120.2
C7—O2—Ni 109.12 (17) N5—C24—C23 123.5 (4)
C14—O3—Ni 126.80 (19) N5—C24—H24 118.3
O1—C1—C2 119.0 (3) C23—C24—H24 118.3
O1—C1—C6 122.4 (3) N4—C25—C26 122.4 (4)
C2—C1—C6 118.6 (3) N4—C25—H25 118.8
C3—C2—C1 121.8 (4) C26—C25—H25 118.8
C3—C2—H2 119.1 C27—C26—C25 119.5 (4)
C1—C2—H2 119.1 C27—C26—H26 120.2
C4—C3—C2 119.6 (4) C25—C26—H26 120.2
C4—C3—H3 120.2 C26—C27—C28 118.8 (4)
C2—C3—H3 120.2 C26—C27—H27 120.6
C3—C4—C5 120.0 (4) C28—C27—H27 120.6
C3—C4—H4 120.0 C27—C28—C29 118.4 (4)
C5—C4—H4 120.0 C27—C28—H28 120.8
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Acta Cryst. (2005). E61, m2526–m2527
C6—C5—H5 119.1 N4—C29—H29 118.0
C5—C6—C1 118.1 (3) C28—C29—H29 118.0
C5—C6—C7 119.5 (3) C31—C30—N6 117.5 (7)
C1—C6—C7 122.4 (3) C31—C30—H30 121.2
O2—C7—N1 126.3 (3) N6—C30—H30 121.2
O2—C7—C6 117.5 (3) C32—C31—C30 119.7 (7)
N1—C7—C6 116.1 (2) C32—C31—H31 120.2
N2—C8—C9 126.0 (3) C30—C31—H31 120.2
N2—C8—H8 117.0 C31—C32—C33 119.4 (8)
C9—C8—H8 117.0 C31—C32—H32 120.3
C10—C9—C14 118.8 (3) C33—C32—H32 120.3
C10—C9—C8 116.8 (3) C34—C33—C32 123.0 (8)
C14—C9—C8 124.2 (3) C34—C33—H33 118.5
C11—C10—C9 123.1 (4) C32—C33—H33 118.5
C11—C10—H10 118.4 C33—C34—N6 121.5 (8)
C9—C10—H10 118.4 C33—C34—H34 119.2
C10—C11—C12 118.3 (4) N6—C34—H34 119.2
C10—C11—H11 120.9 C35—N7—C37 117.2 (5)
C12—C11—H11 120.9 N7—C35—C37i 121.6 (5)
C13—C12—C11 120.1 (4) N7—C35—H35 119.2
C13—C12—H12 120.0 C37i—C35—H35 119.2
C11—C12—H12 120.0 N7—C37—C35i 121.3 (5)
C12—C13—C14 123.3 (4) N7—C37—H37 119.4
C12—C13—H13 118.4 C35i—C37—H37 119.4
C14—C13—H13 118.4
O3—Ni—N4—C29 −137.7 (3) C8—C9—C14—C13 176.9 (3) N2—Ni—N4—C29 −46.0 (3) C19—N3—C15—C16 1.3 (6) O2—Ni—N4—C29 33.1 (3) Ni—N3—C15—C16 177.2 (3) N3—Ni—N4—C29 126.3 (3) N3—C15—C16—C17 −0.8 (6) O3—Ni—N5—C24 −179.8 (3) C15—C16—C17—C18 0.0 (7) N2—Ni—N5—C24 88.5 (3) C16—C17—C18—C19 0.2 (8) O2—Ni—N5—C24 9.5 (3) C15—N3—C19—C18 −1.0 (7) N3—Ni—N5—C24 −83.7 (3) Ni—N3—C19—C18 −177.0 (4) O3—Ni—N5—C20 8.4 (3) C17—C18—C19—N3 0.3 (8) N2—Ni—N5—C20 −83.3 (3) C24—N5—C20—C21 −0.9 (5) O2—Ni—N5—C20 −162.4 (3) Ni—N5—C20—C21 171.4 (3) N3—Ni—N5—C20 104.4 (3) N5—C20—C21—C22 0.3 (6) N2—Ni—O2—C7 −6.51 (19) C20—C21—C22—C23 0.3 (7) N3—Ni—O2—C7 170.54 (19) C21—C22—C23—C24 −0.3 (7) N4—Ni—O2—C7 −99.39 (19) C20—N5—C24—C23 0.9 (5) N5—Ni—O2—C7 81.44 (19) Ni—N5—C24—C23 −171.4 (3) N2—Ni—O3—C14 −6.4 (2) C22—C23—C24—N5 −0.3 (7) N3—Ni—O3—C14 176.5 (2) C29—N4—C25—C26 0.0 (6) N4—Ni—O3—C14 86.4 (2) Ni—N4—C25—C26 −178.2 (3) N5—Ni—O3—C14 −94.3 (2) N4—C25—C26—C27 −0.4 (7) O1—C1—C2—C3 178.6 (4) C25—C26—C27—C28 0.5 (8) C6—C1—C2—C3 −2.1 (6) C26—C27—C28—C29 −0.3 (7) C1—C2—C3—C4 −0.2 (7) C25—N4—C29—C28 0.2 (6) C2—C3—C4—C5 1.7 (7) Ni—N4—C29—C28 178.3 (3) C3—C4—C5—C6 −0.9 (7) C27—C28—C29—N4 −0.1 (7) C4—C5—C6—C1 −1.4 (6) C34—N6—C30—C31 −5.5 (11) C4—C5—C6—C7 177.8 (4) N6—C30—C31—C32 −1.7 (12) O1—C1—C6—C5 −177.9 (3) C30—C31—C32—C33 6.6 (14) C2—C1—C6—C5 2.8 (5) C31—C32—C33—C34 −4.6 (17) O1—C1—C6—C7 2.9 (5) C32—C33—C34—N6 −3.1 (17) C2—C1—C6—C7 −176.4 (3) C30—N6—C34—C33 7.9 (14) Ni—O2—C7—N1 6.9 (4) C37—N7—C35—C37i 0.4 (10)
Ni—O2—C7—C6 −172.3 (2) C35—N7—C37—C35i −0.4 (9)
Symmetry code: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O1—H1···N1 0.82 1.82 2.549 (3) 147
C16—H16···O1ii 0.93 2.58 3.356 (5) 141
C20—H20···O3 0.93 2.43 3.022 (4) 121
C24—H24···O2 0.93 2.47 3.030 (4) 119
C19—H19···O2 0.93 2.52 3.059 (4) 118