trans-(1,8-Dibenzyl-1,3,6,8,10,13-hexa-azacyclo-tetra-deca-ne)diisonicotinatonickel(II).

In the centrosymmetric title compound, [Ni(C(6)H(4)NO(2))(2)(C(22)H(34)N(6))], the Ni(II) ion is bonded to the four secondary N atoms of the macrocyclic ligand in a square-planar fashion and two carboxyl-ate O atoms of the isonicotinate ions in axial positions, resulting in a tetra-gonally distorted octa-hedron. An offset face-to-face π-π stacking inter-action [centroid-centroid distance = 3.674(4) Å] and N-H⋯N and N-H⋯O hydrogen-bonding inter-actions give rise to a one-dimensional supra-molecular structure in the solid state.

Related literature

For related literature, see Hancock (1990 ▶); Jung et al. (1989 ▶); Larionova et al. (2003 ▶); Lee & Suh (2004 ▶); Shetty et al. (1996 ▶); Tsuge et al. (2004 ▶).

Experimental

Crystal data

[Ni(C6H4NO2)2(C22H34N6)]

M = 685.45

Monoclinic,

a = 8.3418 (5) Å

b = 17.3104 (9) Å

c = 10.9596 (6) Å

β = 91.892 (1)°

V = 1581.70 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.67 mm−1

T = 173 (2) K

0.40 × 0.20 × 0.20 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.778, T max = 0.875

9843 measured reflections

3671 independent reflections

3288 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.116

S = 1.29

3671 reflections

214 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.56 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SHELXTL (Sheldrick, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808001116/pk2081sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001116/pk2081Isup2.hkl

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

[Ni(C6H4NO2)2(C22H34N6)]	F000 = 724
Mr = 685.45	Dx = 1.439 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5240 reflections
a = 8.3418 (5) Å	θ = 2.2–28.1º
b = 17.3104 (9) Å	µ = 0.67 mm−1
c = 10.9596 (6) Å	T = 173 (2) K
β = 91.892 (1)º	Block, pink
V = 1581.70 (15) Å3	0.40 × 0.20 × 0.20 mm
Z = 2

Siemens SMART CCD diffractometer	3671 independent reflections
Radiation source: fine-focus sealed tube	3288 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.022
T = 173(2) K	θmax = 28.3º
φ and ω scans	θmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −10→9
Tmin = 0.778, Tmax = 0.875	k = −22→19
9843 measured reflections	l = −14→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0189P)2 + 2.8532P] where P = (Fo2 + 2Fc2)/3
S = 1.29	(Δ/σ)max < 0.001
3671 reflections	Δρmax = 0.52 e Å−3
214 parameters	Δρmin = −0.55 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 2σ(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.

	x	y	z	Uiso*/Ueq
Ni1	0.5000	0.5000	1.0000	0.01570 (13)
O1	0.4295 (2)	0.54216 (12)	0.82075 (17)	0.0223 (4)
O2	0.1901 (3)	0.48759 (12)	0.77448 (18)	0.0279 (5)
N1	0.2943 (3)	0.43532 (13)	1.0093 (2)	0.0185 (5)
H1	0.2407	0.4385	0.9337	0.022*
N2	0.3733 (3)	0.58652 (13)	1.0846 (2)	0.0195 (5)
H2	0.4031	0.5862	1.1671	0.023*
N3	0.5746 (3)	0.68651 (14)	1.0464 (2)	0.0216 (5)
N4	0.3459 (3)	0.59376 (16)	0.3712 (2)	0.0295 (6)
C1	0.3199 (4)	0.35247 (17)	1.0367 (3)	0.0231 (6)
H1A	0.3657	0.3476	1.1209	0.028*
H1B	0.2147	0.3260	1.0340	0.028*
C2	0.1956 (3)	0.47603 (17)	1.0988 (2)	0.0216 (6)
H2A	0.2370	0.4653	1.1828	0.026*
H2B	0.0832	0.4579	1.0915	0.026*
C3	0.2034 (3)	0.56208 (17)	1.0729 (3)	0.0228 (6)
H3A	0.1603	0.5730	0.9895	0.027*
H3B	0.1385	0.5908	1.1318	0.027*
C4	0.4065 (3)	0.66490 (17)	1.0359 (3)	0.0239 (6)
H4A	0.3711	0.6669	0.9488	0.029*
H4B	0.3425	0.7032	1.0805	0.029*
C5	0.6325 (3)	0.68978 (17)	1.1745 (2)	0.0226 (6)
H5A	0.6392	0.6365	1.2069	0.027*
H5B	0.5527	0.7181	1.2223	0.027*
C6	0.7938 (3)	0.72810 (16)	1.1938 (3)	0.0220 (6)
C7	0.9015 (4)	0.69899 (18)	1.2817 (3)	0.0299 (7)
H7	0.8761	0.6531	1.3244	0.036*
C8	1.0459 (4)	0.7364 (2)	1.3077 (3)	0.0361 (8)
H8	1.1184	0.7161	1.3681	0.043*
C9	1.0843 (4)	0.8026 (2)	1.2465 (3)	0.0367 (8)
H9	1.1830	0.8282	1.2645	0.044*
C10	0.9780 (4)	0.8320 (2)	1.1580 (3)	0.0386 (8)
H10	1.0045	0.8777	1.1150	0.046*
C11	0.8342 (4)	0.79516 (18)	1.1324 (3)	0.0291 (7)
H11	0.7620	0.8159	1.0720	0.035*
C12	0.3141 (3)	0.52339 (16)	0.7488 (2)	0.0200 (6)
C13	0.3282 (3)	0.54825 (16)	0.6159 (2)	0.0206 (6)
C14	0.4444 (4)	0.59945 (18)	0.5799 (3)	0.0268 (6)
H14	0.5202	0.6200	0.6378	0.032*
C15	0.4485 (4)	0.6204 (2)	0.4576 (3)	0.0300 (7)
H15	0.5290	0.6558	0.4340	0.036*
C16	0.2331 (4)	0.54476 (19)	0.4082 (3)	0.0280 (7)
H16	0.1572	0.5258	0.3490	0.034*
C17	0.2206 (4)	0.52022 (17)	0.5277 (3)	0.0231 (6)
H17	0.1394	0.4846	0.5489	0.028*

	U11	U22	U33	U12	U13	U23
Ni1	0.0150 (2)	0.0204 (2)	0.0117 (2)	−0.0036 (2)	−0.00054 (16)	0.00087 (19)
O1	0.0235 (10)	0.0286 (11)	0.0145 (9)	−0.0042 (8)	−0.0035 (7)	0.0012 (8)
O2	0.0286 (11)	0.0330 (12)	0.0216 (10)	−0.0085 (9)	−0.0051 (8)	0.0058 (9)
N1	0.0199 (11)	0.0240 (12)	0.0116 (10)	−0.0038 (9)	−0.0006 (9)	−0.0001 (9)
N2	0.0185 (11)	0.0245 (12)	0.0153 (11)	−0.0030 (9)	−0.0017 (9)	0.0005 (9)
N3	0.0226 (12)	0.0229 (12)	0.0190 (12)	−0.0041 (10)	−0.0021 (9)	−0.0005 (9)
N4	0.0334 (14)	0.0398 (16)	0.0154 (12)	0.0069 (12)	0.0004 (10)	0.0028 (11)
C1	0.0277 (15)	0.0266 (15)	0.0150 (13)	−0.0063 (12)	0.0015 (11)	0.0025 (11)
C2	0.0186 (13)	0.0308 (15)	0.0155 (13)	−0.0044 (11)	0.0008 (10)	−0.0033 (11)
C3	0.0185 (14)	0.0298 (16)	0.0201 (14)	−0.0013 (12)	0.0003 (11)	−0.0023 (11)
C4	0.0223 (14)	0.0260 (15)	0.0233 (15)	0.0005 (12)	−0.0027 (11)	0.0022 (12)
C5	0.0256 (15)	0.0257 (15)	0.0166 (13)	−0.0043 (12)	0.0004 (11)	−0.0016 (11)
C6	0.0236 (15)	0.0222 (14)	0.0204 (14)	−0.0019 (11)	0.0016 (11)	−0.0065 (11)
C7	0.0361 (18)	0.0229 (15)	0.0304 (16)	−0.0040 (13)	−0.0032 (13)	0.0029 (13)
C8	0.0323 (18)	0.0322 (18)	0.043 (2)	−0.0009 (14)	−0.0156 (15)	0.0015 (15)
C9	0.0275 (17)	0.039 (2)	0.043 (2)	−0.0089 (15)	−0.0075 (14)	−0.0031 (16)
C10	0.0380 (19)	0.0323 (18)	0.045 (2)	−0.0127 (15)	−0.0030 (16)	0.0091 (15)
C11	0.0291 (16)	0.0286 (16)	0.0292 (16)	−0.0034 (13)	−0.0052 (13)	0.0047 (13)
C12	0.0248 (14)	0.0204 (13)	0.0146 (12)	0.0026 (11)	−0.0015 (10)	−0.0002 (10)
C13	0.0223 (14)	0.0217 (14)	0.0178 (13)	0.0070 (11)	−0.0007 (10)	−0.0019 (11)
C14	0.0297 (16)	0.0338 (17)	0.0166 (14)	−0.0012 (13)	−0.0032 (11)	−0.0001 (12)
C15	0.0321 (17)	0.0389 (18)	0.0192 (14)	−0.0034 (14)	0.0008 (12)	0.0033 (13)
C16	0.0267 (16)	0.0387 (18)	0.0184 (14)	0.0055 (13)	−0.0046 (12)	−0.0060 (12)
C17	0.0236 (14)	0.0253 (15)	0.0204 (14)	0.0018 (11)	−0.0002 (11)	−0.0019 (11)

Ni1—N1i	2.054 (2)	C3—H3B	0.9900
Ni1—N1	2.054 (2)	C4—H4A	0.9900
Ni1—N2i	2.070 (2)	C4—H4B	0.9900
Ni1—N2	2.070 (2)	C5—C6	1.509 (4)
Ni1—O1i	2.1591 (19)	C5—H5A	0.9900
Ni1—O1	2.1591 (19)	C5—H5B	0.9900
O1—C12	1.266 (3)	C6—C11	1.389 (4)
O2—C12	1.246 (4)	C6—C7	1.390 (4)
N1—C2	1.479 (3)	C7—C8	1.389 (5)
N1—C1	1.479 (4)	C7—H7	0.9500
N1—H1	0.9300	C8—C9	1.371 (5)
N2—C3	1.480 (3)	C8—H8	0.9500
N2—C4	1.487 (4)	C9—C10	1.388 (5)
N2—H2	0.9300	C9—H9	0.9500
N3—C4	1.452 (4)	C10—C11	1.380 (4)
N3—C1i	1.453 (4)	C10—H10	0.9500
N3—C5	1.470 (4)	C11—H11	0.9500
N4—C15	1.337 (4)	C12—C13	1.527 (4)
N4—C16	1.340 (4)	C13—C14	1.380 (4)
C1—N3i	1.453 (4)	C13—C17	1.386 (4)
C1—H1A	0.9900	C14—C15	1.391 (4)
C1—H1B	0.9900	C14—H14	0.9500
C2—C3	1.518 (4)	C15—H15	0.9500
C2—H2A	0.9900	C16—C17	1.384 (4)
C2—H2B	0.9900	C16—H16	0.9500
C3—H3A	0.9900	C17—H17	0.9500
N1i—Ni1—N1	180.00 (11)	H3A—C3—H3B	108.4
N1i—Ni1—N2i	86.12 (9)	N3—C4—N2	113.4 (2)
N1—Ni1—N2i	93.88 (9)	N3—C4—H4A	108.9
N1i—Ni1—N2	93.88 (9)	N2—C4—H4A	108.9
N1—Ni1—N2	86.12 (9)	N3—C4—H4B	108.9
N2i—Ni1—N2	180.000 (1)	N2—C4—H4B	108.9
N1i—Ni1—O1i	91.53 (8)	H4A—C4—H4B	107.7
N1—Ni1—O1i	88.47 (8)	N3—C5—C6	114.5 (2)
N2i—Ni1—O1i	92.00 (8)	N3—C5—H5A	108.6
N2—Ni1—O1i	88.00 (8)	C6—C5—H5A	108.6
N1i—Ni1—O1	88.47 (8)	N3—C5—H5B	108.6
N1—Ni1—O1	91.53 (8)	C6—C5—H5B	108.6
N2i—Ni1—O1	88.00 (8)	H5A—C5—H5B	107.6
N2—Ni1—O1	92.00 (8)	C11—C6—C7	118.5 (3)
O1i—Ni1—O1	180.000 (1)	C11—C6—C5	121.9 (3)
C12—O1—Ni1	131.18 (18)	C7—C6—C5	119.4 (3)
C2—N1—C1	114.0 (2)	C8—C7—C6	120.6 (3)
C2—N1—Ni1	104.91 (16)	C8—C7—H7	119.7
C1—N1—Ni1	115.03 (18)	C6—C7—H7	119.7
C2—N1—H1	107.5	C9—C8—C7	120.3 (3)
C1—N1—H1	107.5	C9—C8—H8	119.8
Ni1—N1—H1	107.5	C7—C8—H8	119.8
C3—N2—C4	114.8 (2)	C8—C9—C10	119.6 (3)
C3—N2—Ni1	104.84 (17)	C8—C9—H9	120.2
C4—N2—Ni1	113.30 (17)	C10—C9—H9	120.2
C3—N2—H2	107.9	C11—C10—C9	120.3 (3)
C4—N2—H2	107.9	C11—C10—H10	119.9
Ni1—N2—H2	107.9	C9—C10—H10	119.9
C4—N3—C1i	115.7 (2)	C10—C11—C6	120.7 (3)
C4—N3—C5	111.8 (2)	C10—C11—H11	119.6
C1i—N3—C5	115.5 (2)	C6—C11—H11	119.6
C15—N4—C16	116.4 (3)	O2—C12—O1	127.4 (3)
N3i—C1—N1	114.2 (2)	O2—C12—C13	116.5 (2)
N3i—C1—H1A	108.7	O1—C12—C13	116.1 (2)
N1—C1—H1A	108.7	C14—C13—C17	118.0 (3)
N3i—C1—H1B	108.7	C14—C13—C12	122.1 (3)
N1—C1—H1B	108.7	C17—C13—C12	119.9 (3)
H1A—C1—H1B	107.6	C13—C14—C15	118.9 (3)
N1—C2—C3	108.4 (2)	C13—C14—H14	120.5
N1—C2—H2A	110.0	C15—C14—H14	120.5
C3—C2—H2A	110.0	N4—C15—C14	123.8 (3)
N1—C2—H2B	110.0	N4—C15—H15	118.1
C3—C2—H2B	110.0	C14—C15—H15	118.1
H2A—C2—H2B	108.4	N4—C16—C17	123.8 (3)
N2—C3—C2	108.1 (2)	N4—C16—H16	118.1
N2—C3—H3A	110.1	C17—C16—H16	118.1
C2—C3—H3A	110.1	C16—C17—C13	119.1 (3)
N2—C3—H3B	110.1	C16—C17—H17	120.4
C2—C3—H3B	110.1	C13—C17—H17	120.4
N1i—Ni1—O1—C12	172.2 (2)	C3—N2—C4—N3	−178.8 (2)
N1—Ni1—O1—C12	−7.8 (2)	Ni1—N2—C4—N3	−58.4 (3)
N2i—Ni1—O1—C12	86.0 (2)	C4—N3—C5—C6	−167.4 (2)
N2—Ni1—O1—C12	−94.0 (2)	C1i—N3—C5—C6	57.5 (3)
N2i—Ni1—N1—C2	164.18 (17)	N3—C5—C6—C11	42.2 (4)
N2—Ni1—N1—C2	−15.82 (17)	N3—C5—C6—C7	−142.4 (3)
O1i—Ni1—N1—C2	72.27 (17)	C11—C6—C7—C8	0.3 (5)
O1—Ni1—N1—C2	−107.73 (17)	C5—C6—C7—C8	−175.3 (3)
N2i—Ni1—N1—C1	38.05 (18)	C6—C7—C8—C9	−0.2 (5)
N2—Ni1—N1—C1	−141.95 (18)	C7—C8—C9—C10	−0.2 (6)
O1i—Ni1—N1—C1	−53.85 (18)	C8—C9—C10—C11	0.4 (6)
O1—Ni1—N1—C1	126.15 (18)	C9—C10—C11—C6	−0.4 (5)
N1i—Ni1—N2—C3	165.31 (17)	C7—C6—C11—C10	0.0 (5)
N1—Ni1—N2—C3	−14.69 (17)	C5—C6—C11—C10	175.4 (3)
O1i—Ni1—N2—C3	−103.29 (17)	Ni1—O1—C12—O2	17.8 (4)
O1—Ni1—N2—C3	76.71 (17)	Ni1—O1—C12—C13	−162.89 (18)
N1i—Ni1—N2—C4	39.44 (19)	O2—C12—C13—C14	168.4 (3)
N1—Ni1—N2—C4	−140.56 (19)	O1—C12—C13—C14	−11.0 (4)
O1i—Ni1—N2—C4	130.83 (18)	O2—C12—C13—C17	−10.5 (4)
O1—Ni1—N2—C4	−49.17 (18)	O1—C12—C13—C17	170.1 (3)
C2—N1—C1—N3i	−176.2 (2)	C17—C13—C14—C15	−0.1 (4)
Ni1—N1—C1—N3i	−54.9 (3)	C12—C13—C14—C15	−179.0 (3)
C1—N1—C2—C3	170.1 (2)	C16—N4—C15—C14	0.7 (5)
Ni1—N1—C2—C3	43.4 (2)	C13—C14—C15—N4	−0.1 (5)
C4—N2—C3—C2	167.2 (2)	C15—N4—C16—C17	−1.3 (5)
Ni1—N2—C3—C2	42.2 (2)	N4—C16—C17—C13	1.1 (5)
N1—C2—C3—N2	−59.6 (3)	C14—C13—C17—C16	−0.4 (4)
C1i—N3—C4—N2	72.6 (3)	C12—C13—C17—C16	178.6 (3)
C5—N3—C4—N2	−62.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.93	1.97	2.838 (3)	154
N2—H2···N4ii	0.93	2.31	3.160 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.93	1.97	2.838 (3)	154
N2—H2⋯N4i	0.93	2.31	3.160 (3)	152

Symmetry code: (i) .