Second monoclinic modification of cyclo-hexane-1,1-dicarbonitrile.

In the title compound, C(8)H(10)N(2), the cyclo-hexane ring adopts a chair conformation. he crystal structure of the previously reported monoclinic modification have intramolecular CN⋯CN and C-H⋯N interactions. These types of interaction are not present in this new modification whose crystal structure is built up by van der Waals interactions.

Related literature

For the previously reported monoclinic modification, see: Echeverria et al. (1995 ▶). For synthetic methods, see: Tsai et al. (2003 ▶); Suissa et al. (1977 ▶); Julia & Maumy (1969 ▶). For puckering parameters see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C8H10N2

M = 134.18

Monoclinic,

a = 8.9300 (5) Å

b = 8.3656 (5) Å

c = 9.8725 (6) Å

β = 92.662 (1)°

V = 736.73 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.30 × 0.30 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.978, T max = 0.978

9584 measured reflections

2794 independent reflections

2236 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.105

S = 1.03

2794 reflections

91 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023592/ng5170sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023592/ng5170Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023592/ng5170Isup3.cml

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

C8H10N2	F(000) = 288
Mr = 134.18	Dx = 1.210 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2571 reflections
a = 8.9300 (5) Å	θ = 3.0–33.1°
b = 8.3656 (5) Å	µ = 0.08 mm−1
c = 9.8725 (6) Å	T = 100 K
β = 92.662 (1)°	Prism, colourless
V = 736.73 (8) Å3	0.30 × 0.30 × 0.30 mm
Z = 4

Bruker APEXII CCD diffractometer	2794 independent reflections
Radiation source: fine-focus sealed tube	2236 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 33.2°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −13→13
Tmin = 0.978, Tmax = 0.978	k = −12→12
9584 measured reflections	l = −15→14

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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F2) = 0.105	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0492P)2 + 0.1357P] where P = (Fo2 + 2Fc2)/3
2794 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
N1	0.36573 (9)	−0.12113 (9)	0.57950 (8)	0.02114 (17)
N2	−0.02890 (8)	0.15605 (9)	0.63201 (8)	0.01948 (16)
C1	0.24232 (8)	0.16105 (9)	0.53895 (8)	0.01226 (14)
C2	0.23203 (9)	0.19844 (9)	0.38467 (8)	0.01370 (15)
H2A	0.3327	0.1888	0.3476	0.016*
H2B	0.1652	0.1197	0.3376	0.016*
C3	0.17144 (9)	0.36675 (10)	0.35831 (9)	0.01563 (16)
H3A	0.0672	0.3734	0.3878	0.019*
H3B	0.1701	0.3895	0.2598	0.019*
C4	0.26762 (9)	0.49156 (9)	0.43440 (9)	0.01663 (16)
H4A	0.2237	0.5990	0.4185	0.020*
H4B	0.3697	0.4915	0.3992	0.020*
C5	0.27741 (9)	0.45676 (10)	0.58644 (8)	0.01565 (16)
H5A	0.3437	0.5367	0.6326	0.019*
H5B	0.1765	0.4671	0.6230	0.019*
C6	0.33813 (9)	0.28925 (9)	0.61680 (8)	0.01401 (15)
H6A	0.3367	0.2685	0.7155	0.017*
H6B	0.4433	0.2823	0.5898	0.017*
C7	0.30994 (9)	0.00103 (10)	0.56201 (8)	0.01494 (15)
C8	0.08948 (9)	0.15673 (9)	0.59186 (8)	0.01406 (15)

	U11	U22	U33	U12	U13	U23
N1	0.0225 (3)	0.0166 (3)	0.0245 (4)	0.0026 (3)	0.0035 (3)	0.0023 (3)
N2	0.0181 (3)	0.0193 (3)	0.0213 (4)	−0.0012 (3)	0.0039 (3)	−0.0003 (3)
C1	0.0127 (3)	0.0109 (3)	0.0134 (3)	0.0006 (2)	0.0021 (2)	0.0006 (2)
C2	0.0170 (3)	0.0128 (3)	0.0115 (3)	−0.0012 (3)	0.0017 (3)	−0.0003 (3)
C3	0.0179 (3)	0.0144 (3)	0.0145 (3)	0.0001 (3)	−0.0010 (3)	0.0019 (3)
C4	0.0214 (4)	0.0116 (3)	0.0169 (4)	−0.0007 (3)	0.0006 (3)	0.0011 (3)
C5	0.0188 (3)	0.0124 (3)	0.0157 (4)	0.0003 (3)	0.0003 (3)	−0.0021 (3)
C6	0.0141 (3)	0.0136 (3)	0.0141 (3)	−0.0002 (2)	−0.0007 (3)	−0.0009 (3)
C7	0.0156 (3)	0.0143 (3)	0.0152 (4)	−0.0005 (3)	0.0032 (3)	0.0007 (3)
C8	0.0161 (3)	0.0125 (3)	0.0136 (3)	−0.0002 (3)	0.0009 (3)	0.0004 (3)

N1—C7	1.1465 (11)	C3—H3A	0.9900
N2—C8	1.1462 (11)	C3—H3B	0.9900
C1—C7	1.4818 (11)	C4—C5	1.5275 (12)
C1—C8	1.4843 (11)	C4—H4A	0.9900
C1—C6	1.5530 (11)	C4—H4B	0.9900
C1—C2	1.5535 (11)	C5—C6	1.5272 (11)
C2—C3	1.5265 (11)	C5—H5A	0.9900
C2—H2A	0.9900	C5—H5B	0.9900
C2—H2B	0.9900	C6—H6A	0.9900
C3—C4	1.5272 (11)	C6—H6B	0.9900
C7—C1—C8	107.39 (6)	C3—C4—H4A	109.4
C7—C1—C6	109.67 (6)	C5—C4—H4A	109.4
C8—C1—C6	109.70 (6)	C3—C4—H4B	109.4
C7—C1—C2	109.73 (6)	C5—C4—H4B	109.4
C8—C1—C2	109.66 (6)	H4A—C4—H4B	108.0
C6—C1—C2	110.63 (6)	C6—C5—C4	111.80 (7)
C3—C2—C1	110.93 (6)	C6—C5—H5A	109.3
C3—C2—H2A	109.5	C4—C5—H5A	109.3
C1—C2—H2A	109.5	C6—C5—H5B	109.3
C3—C2—H2B	109.5	C4—C5—H5B	109.3
C1—C2—H2B	109.5	H5A—C5—H5B	107.9
H2A—C2—H2B	108.0	C5—C6—C1	110.74 (6)
C2—C3—C4	111.10 (6)	C5—C6—H6A	109.5
C2—C3—H3A	109.4	C1—C6—H6A	109.5
C4—C3—H3A	109.4	C5—C6—H6B	109.5
C2—C3—H3B	109.4	C1—C6—H6B	109.5
C4—C3—H3B	109.4	H6A—C6—H6B	108.1
H3A—C3—H3B	108.0	N1—C7—C1	178.29 (8)
C3—C4—C5	110.99 (7)	N2—C8—C1	178.83 (8)
C7—C1—C2—C3	−176.59 (6)	C8—C1—C6—C5	−66.44 (8)
C8—C1—C2—C3	65.69 (8)	C2—C1—C6—C5	54.66 (8)
C6—C1—C2—C3	−55.45 (8)	C8—C1—C7—N1	−161 (3)
C1—C2—C3—C4	56.61 (9)	C6—C1—C7—N1	−42 (3)
C2—C3—C4—C5	−56.87 (9)	C2—C1—C7—N1	80 (3)
C3—C4—C5—C6	56.58 (9)	C7—C1—C8—N2	−179 (100)
C4—C5—C6—C1	−55.55 (9)	C6—C1—C8—N2	62 (4)
C7—C1—C6—C5	175.84 (7)	C2—C1—C8—N2	−60 (4)