1,4-Bis(2-diazo-acet-yl)piperazine.

The asymmetric unit of the title compound, C8H10N6O2, contains one-half mol-ecule, which is completed by a crystallographic center of symmetry. The piperazine ring adopts a chair conformation. In the crystal, weak C-H⋯O inter-actions link the mol-ecules into layers parallel to the bc plane. The crystal packing also exhibits short N⋯N contacts of 3.0467 (16) Å between the terminal diazo N atoms from neighbouring mol-ecules.

Related literature

For related structures in the Cambridge Structural Database (Version 5.34 of November 2012; Allen, 2002 ▶), see: Kaupang (2010 ▶); Kaupang et al. (2010 ▶, 2011 ▶); Aliev et al. (1980 ▶); Fitzgerald & Jensen (1978 ▶); Hope & Black (1972 ▶). For normal bond lengths in organic compounds, see: Allen et al. (1987 ▶). For synthetic details, see: Kaupang & Bonge-Hansen (2013 ▶); Kaupang (2010 ▶); Toma et al. (2007 ▶). For the synthesis of other diazo­acetamides with a 1,4-di­aza six-membered ring, see: Kaupang (2010 ▶); Mickelson et al. (1996 ▶). For the synthesis of other diazo­acetamides, see: Ouihia et al. (1993 ▶). For the Chemical Abstracts Service, see: American Chemical Society (2008 ▶). For graph-set notation for hydrogen-bonding patterns, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C8H10N6O2

M = 222.22

Monoclinic,

a = 4.0630 (7) Å

b = 9.0941 (15) Å

c = 13.230 (2) Å

β = 94.453 (2)°

V = 487.38 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 105 K

1.4 × 0.2 × 0.2 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.859, T max = 0.977

4255 measured reflections

1190 independent reflections

1013 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.090

S = 1.04

1190 reflections

82 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813018801/cv5412sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018801/cv5412Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813018801/cv5412Isup3.cml

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

C8H10N6O2	F(000) = 232
Mr = 222.22	Dx = 1.514 Mg m−3
Monoclinic, P21/c	Melting point: 382 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 4.0630 (7) Å	Cell parameters from 1727 reflections
b = 9.0941 (15) Å	θ = 2.7–28.7°
c = 13.230 (2) Å	µ = 0.12 mm−1
β = 94.453 (2)°	T = 105 K
V = 487.38 (14) Å3	Needle, yellow
Z = 2	1.4 × 0.2 × 0.2 mm

Bruker APEXII CCD diffractometer	1190 independent reflections
Radiation source: fine-focus sealed tube	1013 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 8.3 pixels mm-1	θmax = 28.7°, θmin = 2.7°
Sets of exposures each taken over 0.5° ω rotation scans	h = −5→5
Absorption correction: multi-scan (SADABS; Bruker, 2007)	k = −11→11
Tmin = 0.859, Tmax = 0.977	l = −17→17
4255 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0478P)2 + 0.1317P] where P = (Fo2 + 2Fc2)/3
1190 reflections	(Δ/σ)max < 0.001
82 parameters	Δρmax = 0.30 e Å−3
3 restraints	Δρmin = −0.22 e Å−3

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
C1	0.1936 (3)	0.09488 (12)	0.31650 (8)	0.0164 (2)
C2	0.2433 (3)	−0.01250 (13)	0.23807 (8)	0.0206 (3)
H21	0.165 (3)	−0.1064 (14)	0.2306 (11)	0.025*
C3	−0.0658 (3)	−0.10152 (12)	0.41721 (8)	0.0168 (2)
H31	0.016 (3)	−0.1708 (14)	0.3686 (10)	0.020*
H32	−0.308 (3)	−0.1005 (15)	0.4067 (10)	0.020*
C4	−0.0370 (3)	0.15403 (11)	0.47597 (8)	0.0169 (2)
H41	−0.2791	0.1688	0.4685	0.020*
H42	0.0701	0.2495	0.4638	0.020*
N1	0.0575 (2)	0.04673 (10)	0.40139 (7)	0.0165 (2)
N2	0.4038 (2)	0.03769 (10)	0.16317 (7)	0.0208 (2)
N3	0.5432 (3)	0.08327 (13)	0.10006 (8)	0.0295 (3)
O1	0.2787 (2)	0.22436 (9)	0.30680 (6)	0.0208 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0158 (5)	0.0172 (5)	0.0158 (5)	0.0018 (4)	−0.0009 (4)	0.0016 (4)
C2	0.0285 (6)	0.0176 (5)	0.0162 (5)	−0.0020 (4)	0.0047 (4)	0.0010 (4)
C3	0.0204 (5)	0.0141 (5)	0.0162 (5)	−0.0021 (4)	0.0026 (4)	−0.0006 (4)
C4	0.0202 (5)	0.0142 (5)	0.0167 (5)	0.0009 (4)	0.0030 (4)	−0.0012 (4)
N1	0.0221 (4)	0.0131 (4)	0.0145 (4)	−0.0008 (3)	0.0035 (3)	−0.0006 (3)
N2	0.0264 (5)	0.0189 (5)	0.0171 (5)	0.0024 (4)	0.0021 (4)	−0.0006 (4)
N3	0.0395 (6)	0.0282 (6)	0.0222 (5)	−0.0010 (5)	0.0110 (5)	0.0007 (4)
O1	0.0282 (4)	0.0154 (4)	0.0193 (4)	−0.0016 (3)	0.0047 (3)	0.0017 (3)

C1—O1	1.2367 (14)	C3—H31	0.978 (12)
C1—N1	1.3621 (13)	C3—H32	0.985 (12)
C1—C2	1.4504 (16)	C4—N1	1.4602 (13)
C2—N2	1.3099 (14)	C4—H41	0.9900
C2—H21	0.915 (12)	C4—H42	0.9900
C3—N1	1.4589 (13)	N2—N3	1.1239 (14)
C3—C4i	1.5193 (15)
O1—C1—N1	121.76 (10)	H31—C3—H32	107.6 (11)
O1—C1—C2	120.75 (10)	N1—C4—C3i	110.54 (9)
N1—C1—C2	117.48 (10)	N1—C4—H41	109.5
N2—C2—C1	114.31 (10)	C3i—C4—H41	109.5
N2—C2—H21	115.7 (9)	N1—C4—H42	109.5
C1—C2—H21	129.7 (9)	C3i—C4—H42	109.5
N1—C3—C4i	110.57 (9)	H41—C4—H42	108.1
N1—C3—H31	111.3 (8)	C1—N1—C3	125.53 (9)
C4i—C3—H31	109.1 (8)	C1—N1—C4	119.16 (9)
N1—C3—H32	108.8 (8)	C3—N1—C4	114.17 (8)
C4i—C3—H32	109.5 (8)	N3—N2—C2	178.58 (12)
O1—C1—C2—N2	4.86 (16)	C2—C1—N1—C4	−171.95 (9)
N1—C1—C2—N2	−173.69 (9)	C4i—C3—N1—C1	137.76 (10)
O1—C1—N1—C3	176.58 (10)	C4i—C3—N1—C4	−54.61 (12)
C2—C1—N1—C3	−4.88 (15)	C3i—C4—N1—C1	−136.92 (9)
O1—C1—N1—C4	9.51 (15)	C3i—C4—N1—C3	54.59 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H21···O1ii	0.92 (1)	2.39 (1)	3.2219 (15)	151 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H21⋯O1i	0.92 (1)	2.39 (1)	3.2219 (15)	151 (1)

Symmetry code: (i) .