trans-Diazido-(1,8-dibenzyl-1,3,6,8,10,13-hexa-azacyclo-tetra-deca-ne)nickel(II).

In the centrosymmetric title compound, [Ni(N(3))(2)(C(22)H(34)N(6))], the Ni(II) ion is coordinated by the four secondary N atoms of the macrocyclic ligand in a square-planar fashion with two N atoms of the azide ions in axial positions, resulting in a tetra-gonally distorted octa-hedron. An N-H⋯N hydrogen-bonding inter-action between the secondary amine N atom of the macrocycle and an adjacent azide ion gives rise to a chain structure.

Related literature

For related literature, see: Hancock (1990 ▶); Jacquinot & Hauser (2003 ▶); Jung et al. (1989 ▶); Larionova et al. (2003 ▶); Min & Suh (2001 ▶); Liu et al. (2006 ▶); Tsuge et al. (2004 ▶).

Experimental

Crystal data

[Ni(N3)2(C22H34N6)]

M = 525.32

Monoclinic,

a = 10.2150 (5) Å

b = 15.8337 (9) Å

c = 7.5477 (4) Å

β = 92.817 (1)°

V = 1219.30 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.83 mm−1

T = 173 (2) K

0.50 × 0.20 × 0.20 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.733, T max = 0.847

7464 measured reflections

2820 independent reflections

2456 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.092

S = 1.19

2820 reflections

160 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT and 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/S1600536808018199/er2057sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018199/er2057Isup2.hkl

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

[Ni(N3)2(C22H34N6)]	F000 = 556
Mr = 525.32	Dx = 1.431 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2820 reflections
a = 10.2150 (5) Å	θ = 2.0–28.3º
b = 15.8337 (9) Å	µ = 0.83 mm−1
c = 7.5477 (4) Å	T = 173 (2) K
β = 92.817 (1)º	Block, violet
V = 1219.30 (11) Å3	0.50 × 0.20 × 0.20 mm
Z = 2

Siemens SMART CCD diffractometer	2820 independent reflections
Radiation source: fine-focus sealed tube	2456 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
T = 173(2) K	θmax = 28.3º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −13→11
Tmin = 0.733, Tmax = 0.847	k = −17→20
7464 measured reflections	l = −9→9

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0239P)2 + 1.3575P] where P = (Fo2 + 2Fc2)/3
S = 1.19	(Δ/σ)max < 0.001
2820 reflections	Δρmax = 0.42 e Å−3
160 parameters	Δρmin = −0.29 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 > 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.

	x	y	z	Uiso*/Ueq
Ni1	0.5000	1.0000	0.0000	0.01702 (11)
N1	0.37796 (18)	0.89900 (12)	0.0535 (2)	0.0213 (4)
H1	0.3964	0.8821	0.1701	0.026*
N2	0.20050 (19)	0.99153 (13)	0.1463 (2)	0.0243 (4)
N3	0.38842 (18)	1.08789 (12)	0.1271 (2)	0.0204 (4)
H3	0.4085	1.0836	0.2483	0.024*
N4	0.6135 (2)	0.97898 (13)	0.2449 (2)	0.0254 (4)
N5	0.57874 (18)	0.93204 (12)	0.3563 (2)	0.0221 (4)
N6	0.5460 (2)	0.88500 (14)	0.4654 (3)	0.0315 (5)
C1	0.4175 (2)	0.83010 (15)	−0.0648 (3)	0.0268 (5)
H1A	0.3791	0.8395	−0.1862	0.032*
H1B	0.3852	0.7753	−0.0213	0.032*
C2	0.2360 (2)	0.92198 (15)	0.0349 (3)	0.0240 (5)
H2A	0.2139	0.9369	−0.0904	0.029*
H2B	0.1831	0.8720	0.0644	0.029*
C3	0.2447 (2)	1.07476 (15)	0.0969 (3)	0.0255 (5)
H3A	0.1979	1.1175	0.1658	0.031*
H3B	0.2208	1.0842	−0.0303	0.031*
C4	0.4333 (2)	1.17143 (15)	0.0675 (3)	0.0258 (5)
H4A	0.4050	1.2159	0.1495	0.031*
H4B	0.3948	1.1839	−0.0526	0.031*
C5	0.2105 (2)	0.97543 (16)	0.3375 (3)	0.0256 (5)
H5A	0.1964	1.0291	0.4012	0.031*
H5B	0.3002	0.9555	0.3709	0.031*
C6	0.1129 (2)	0.91069 (15)	0.3963 (3)	0.0230 (5)
C7	0.1481 (3)	0.85575 (17)	0.5339 (3)	0.0302 (5)
H7	0.2352	0.8566	0.5841	0.036*
C8	0.0580 (3)	0.79974 (17)	0.5991 (3)	0.0359 (6)
H8	0.0830	0.7633	0.6948	0.043*
C9	−0.0681 (3)	0.79699 (16)	0.5245 (3)	0.0322 (6)
H9	−0.1298	0.7582	0.5679	0.039*
C10	−0.1042 (2)	0.85094 (16)	0.3866 (3)	0.0288 (5)
H10	−0.1910	0.8491	0.3352	0.035*
C11	−0.0144 (2)	0.90777 (15)	0.3228 (3)	0.0254 (5)
H11	−0.0401	0.9448	0.2284	0.031*

	U11	U22	U33	U12	U13	U23
Ni1	0.0202 (2)	0.01814 (19)	0.01269 (18)	−0.00082 (17)	0.00037 (13)	0.00017 (16)
N1	0.0243 (10)	0.0257 (10)	0.0140 (8)	−0.0017 (8)	0.0009 (7)	−0.0004 (7)
N2	0.0238 (9)	0.0284 (11)	0.0210 (9)	−0.0012 (8)	0.0040 (7)	−0.0004 (8)
N3	0.0245 (10)	0.0224 (10)	0.0144 (8)	−0.0005 (8)	0.0011 (7)	0.0005 (7)
N4	0.0283 (10)	0.0301 (11)	0.0174 (9)	0.0000 (8)	−0.0017 (8)	0.0042 (8)
N5	0.0216 (10)	0.0257 (10)	0.0187 (9)	0.0035 (8)	−0.0029 (7)	−0.0055 (8)
N6	0.0390 (12)	0.0323 (12)	0.0232 (10)	−0.0042 (10)	0.0017 (9)	0.0044 (9)
C1	0.0291 (13)	0.0229 (12)	0.0287 (12)	−0.0041 (10)	0.0040 (9)	−0.0039 (9)
C2	0.0238 (11)	0.0306 (13)	0.0175 (10)	−0.0050 (10)	0.0010 (8)	−0.0025 (9)
C3	0.0245 (12)	0.0289 (13)	0.0230 (11)	0.0022 (10)	0.0005 (9)	0.0011 (9)
C4	0.0310 (13)	0.0199 (11)	0.0267 (12)	0.0019 (10)	0.0029 (9)	−0.0011 (9)
C5	0.0249 (12)	0.0330 (13)	0.0190 (11)	−0.0031 (10)	0.0019 (9)	−0.0041 (9)
C6	0.0263 (12)	0.0256 (12)	0.0174 (10)	0.0019 (10)	0.0038 (8)	−0.0053 (9)
C7	0.0308 (13)	0.0342 (14)	0.0249 (12)	0.0026 (11)	−0.0037 (10)	0.0015 (10)
C8	0.0493 (16)	0.0319 (14)	0.0263 (13)	0.0015 (12)	0.0006 (11)	0.0077 (10)
C9	0.0386 (15)	0.0278 (13)	0.0312 (13)	−0.0065 (11)	0.0124 (11)	−0.0010 (10)
C10	0.0225 (12)	0.0343 (14)	0.0300 (12)	0.0001 (10)	0.0060 (9)	−0.0056 (10)
C11	0.0238 (12)	0.0283 (12)	0.0243 (11)	0.0053 (10)	0.0033 (9)	0.0008 (9)

Ni1—N3	2.0650 (18)	C2—H2B	0.9900
Ni1—N3i	2.0650 (18)	C3—H3A	0.9900
Ni1—N1	2.0795 (19)	C3—H3B	0.9900
Ni1—N1i	2.0795 (19)	C4—C1i	1.526 (3)
Ni1—N4i	2.1592 (19)	C4—H4A	0.9900
Ni1—N4	2.1592 (19)	C4—H4B	0.9900
N1—C1	1.479 (3)	C5—C6	1.512 (3)
N1—C2	1.495 (3)	C5—H5A	0.9900
N1—H1	0.9300	C5—H5B	0.9900
N2—C2	1.443 (3)	C6—C7	1.389 (3)
N2—C3	1.448 (3)	C6—C11	1.389 (3)
N2—C5	1.464 (3)	C7—C8	1.385 (4)
N3—C4	1.477 (3)	C7—H7	0.9500
N3—C3	1.489 (3)	C8—C9	1.381 (4)
N3—H3	0.9300	C8—H8	0.9500
N4—N5	1.189 (3)	C9—C10	1.383 (4)
N5—N6	1.171 (3)	C9—H9	0.9500
C1—C4i	1.526 (3)	C10—C11	1.388 (3)
C1—H1A	0.9900	C10—H10	0.9500
C1—H1B	0.9900	C11—H11	0.9500
C2—H2A	0.9900
N3—Ni1—N3i	180.0	N1—C2—H2A	108.8
N3—Ni1—N1	94.48 (7)	N2—C2—H2B	108.8
N3i—Ni1—N1	85.52 (7)	N1—C2—H2B	108.8
N3—Ni1—N1i	85.52 (7)	H2A—C2—H2B	107.7
N3i—Ni1—N1i	94.48 (7)	N2—C3—N3	113.92 (19)
N1—Ni1—N1i	180.0	N2—C3—H3A	108.8
N3—Ni1—N4i	90.49 (7)	N3—C3—H3A	108.8
N3i—Ni1—N4i	89.51 (7)	N2—C3—H3B	108.8
N1—Ni1—N4i	89.03 (7)	N3—C3—H3B	108.8
N1i—Ni1—N4i	90.97 (7)	H3A—C3—H3B	107.7
N3—Ni1—N4	89.51 (7)	N3—C4—C1i	108.36 (19)
N3i—Ni1—N4	90.49 (7)	N3—C4—H4A	110.0
N1—Ni1—N4	90.97 (7)	C1i—C4—H4A	110.0
N1i—Ni1—N4	89.03 (7)	N3—C4—H4B	110.0
N4i—Ni1—N4	180.00 (10)	C1i—C4—H4B	110.0
C1—N1—C2	114.54 (17)	H4A—C4—H4B	108.4
C1—N1—Ni1	105.41 (13)	N2—C5—C6	113.11 (19)
C2—N1—Ni1	112.49 (14)	N2—C5—H5A	109.0
C1—N1—H1	108.1	C6—C5—H5A	109.0
C2—N1—H1	108.1	N2—C5—H5B	109.0
Ni1—N1—H1	108.1	C6—C5—H5B	109.0
C2—N2—C3	117.02 (18)	H5A—C5—H5B	107.8
C2—N2—C5	115.73 (19)	C7—C6—C11	118.8 (2)
C3—N2—C5	113.87 (19)	C7—C6—C5	119.6 (2)
C4—N3—C3	113.36 (18)	C11—C6—C5	121.5 (2)
C4—N3—Ni1	105.99 (13)	C8—C7—C6	121.0 (2)
C3—N3—Ni1	113.40 (14)	C8—C7—H7	119.5
C4—N3—H3	108.0	C6—C7—H7	119.5
C3—N3—H3	108.0	C9—C8—C7	119.9 (2)
Ni1—N3—H3	108.0	C9—C8—H8	120.1
N5—N4—Ni1	122.34 (16)	C7—C8—H8	120.1
N6—N5—N4	179.0 (2)	C8—C9—C10	119.7 (2)
N1—C1—C4i	108.84 (19)	C8—C9—H9	120.1
N1—C1—H1A	109.9	C10—C9—H9	120.1
C4i—C1—H1A	109.9	C9—C10—C11	120.4 (2)
N1—C1—H1B	109.9	C9—C10—H10	119.8
C4i—C1—H1B	109.9	C11—C10—H10	119.8
H1A—C1—H1B	108.3	C10—C11—C6	120.3 (2)
N2—C2—N1	113.67 (18)	C10—C11—H11	119.9
N2—C2—H2A	108.8	C6—C11—H11	119.9
N3—Ni1—N1—C1	165.54 (14)	C3—N2—C2—N1	72.2 (3)
N3i—Ni1—N1—C1	−14.46 (14)	C5—N2—C2—N1	−66.4 (2)
N4i—Ni1—N1—C1	75.12 (14)	C1—N1—C2—N2	−177.66 (18)
N4—Ni1—N1—C1	−104.88 (14)	Ni1—N1—C2—N2	−57.3 (2)
N3—Ni1—N1—C2	40.06 (14)	C2—N2—C3—N3	−71.2 (3)
N3i—Ni1—N1—C2	−139.94 (14)	C5—N2—C3—N3	68.1 (2)
N4i—Ni1—N1—C2	−50.35 (14)	C4—N3—C3—N2	176.97 (18)
N4—Ni1—N1—C2	129.65 (14)	Ni1—N3—C3—N2	56.1 (2)
N1—Ni1—N3—C4	−164.63 (14)	C3—N3—C4—C1i	−166.97 (18)
N1i—Ni1—N3—C4	15.37 (14)	Ni1—N3—C4—C1i	−41.96 (19)
N4i—Ni1—N3—C4	−75.56 (14)	C2—N2—C5—C6	−66.6 (3)
N4—Ni1—N3—C4	104.44 (14)	C3—N2—C5—C6	153.5 (2)
N1—Ni1—N3—C3	−39.65 (15)	N2—C5—C6—C7	145.0 (2)
N1i—Ni1—N3—C3	140.35 (15)	N2—C5—C6—C11	−38.7 (3)
N4i—Ni1—N3—C3	49.42 (15)	C11—C6—C7—C8	−0.9 (4)
N4—Ni1—N3—C3	−130.58 (15)	C5—C6—C7—C8	175.5 (2)
N3—Ni1—N4—N5	83.63 (19)	C6—C7—C8—C9	1.2 (4)
N3i—Ni1—N4—N5	−96.37 (19)	C7—C8—C9—C10	−0.8 (4)
N1—Ni1—N4—N5	−10.84 (19)	C8—C9—C10—C11	0.0 (4)
N1i—Ni1—N4—N5	169.16 (19)	C9—C10—C11—C6	0.3 (4)
C2—N1—C1—C4i	165.51 (18)	C7—C6—C11—C10	0.1 (3)
Ni1—N1—C1—C4i	41.3 (2)	C5—C6—C11—C10	−176.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N6ii	0.93	2.24	3.145 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N6i	0.93	2.24	3.145 (3)	163

Symmetry code: (i) .