2,2'-[1,2-Phenyl-enebis(aza-nedi-yl)]di-aceto-nitrile.

The title compound, C10H10N4, shows chemical but not crystallographic C2 symmetry. The two cyano-methyl groups are located in an anti position with respect to the aromatic ring. In the crystal, mol-ecules form parallel ladder-like tapes linked through two N-H⋯N hydrogen bonds. Further weak intra-molecular N-H⋯N hydrogen bonding is responsible for the elongation of one of the Caromatic-N bonds.

Related literature

For general background to the title compound, see: Rivera et al. (2010 ▶). For related structures, see: Rivera et al. (2010 ▶, 2011 ▶); Silversides et al. (2006 ▶).

Experimental

Crystal data

C10H10N4

M = 186.2

Orthorhombic,

a = 7.6404 (3) Å

b = 15.1703 (7) Å

c = 15.9168 (7) Å

V = 1844.87 (14) Å3

Z = 8

Cu Kα radiation

μ = 0.69 mm−1

T = 120 K

0.17 × 0.15 × 0.10 mm

Data collection

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.68, T max = 1

9893 measured reflections

1641 independent reflections

1359 reflections with I > 3σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.104

S = 1.55

1641 reflections

133 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812047538/bt6866sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047538/bt6866Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047538/bt6866Isup3.cml

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

C10H10N4	Dx = 1.341 Mg m−3
Mr = 186.2	Melting point: 399 K
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4237 reflections
a = 7.6404 (3) Å	θ = 4.0–67.0°
b = 15.1703 (7) Å	µ = 0.69 mm−1
c = 15.9168 (7) Å	T = 120 K
V = 1844.87 (14) Å3	Polygon shape, white
Z = 8	0.17 × 0.15 × 0.10 mm
F(000) = 784

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer	1641 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1359 reflections with I > 3σ(I)
Mirror monochromator	Rint = 0.061
Detector resolution: 10.3784 pixels mm-1	θmax = 67.2°, θmin = 5.6°
ω scans	h = −7→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −18→18
Tmin = 0.68, Tmax = 1	l = −18→16
9893 measured reflections

Refinement on F2	34 constraints
R[F2 > 2σ(F2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104	Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2)
S = 1.55	(Δ/σ)max = 0.005
1641 reflections	Δρmax = 0.16 e Å−3
133 parameters	Δρmin = −0.20 e Å−3
0 restraints

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	Uiso*/Ueq
N1	0.67776 (14)	0.46314 (7)	0.09105 (8)	0.0197 (3)
N2	0.59009 (13)	0.37473 (8)	−0.05397 (8)	0.0182 (3)
N3	0.75959 (16)	0.31452 (9)	0.25065 (9)	0.0316 (4)
N4	0.68740 (17)	0.42625 (9)	−0.25896 (9)	0.0314 (4)
C1	0.67383 (17)	0.35295 (9)	0.20428 (10)	0.0228 (4)
C2	0.62292 (17)	0.38628 (9)	−0.20642 (10)	0.0227 (4)
C3	0.81190 (16)	0.41747 (8)	0.04529 (9)	0.0179 (4)
C4	0.76583 (16)	0.37282 (8)	−0.02878 (9)	0.0176 (4)
C5	0.54231 (16)	0.33892 (9)	−0.13496 (9)	0.0200 (4)
C6	0.89448 (16)	0.32671 (9)	−0.07229 (10)	0.0203 (4)
C7	0.57084 (17)	0.40361 (9)	0.14220 (10)	0.0215 (4)
C8	1.11225 (17)	0.37219 (9)	0.02841 (11)	0.0248 (4)
C9	0.98466 (17)	0.41713 (9)	0.07282 (10)	0.0224 (4)
C10	1.06689 (17)	0.32645 (10)	−0.04320 (10)	0.0238 (4)
H1c5	0.417265	0.339719	−0.140823	0.024*
H2c5	0.57431	0.277778	−0.137292	0.024*
H1c6	0.864639	0.294979	−0.122465	0.0244*
H1c7	0.508788	0.363609	0.106188	0.0258*
H2c7	0.481985	0.436862	0.17073	0.0258*
H1c8	1.23154	0.372856	0.047341	0.0298*
H1c9	1.015681	0.44837	0.123117	0.0268*
H1c10	1.154716	0.294105	−0.073369	0.0286*
H1	0.732 (2)	0.5050 (12)	0.1255 (12)	0.0237*
H2	0.536 (2)	0.4245 (12)	−0.0403 (12)	0.0219*

	U11	U22	U33	U12	U13	U23
N1	0.0140 (5)	0.0231 (6)	0.0221 (7)	0.0001 (4)	−0.0013 (5)	−0.0013 (5)
N2	0.0087 (5)	0.0257 (6)	0.0202 (7)	0.0023 (4)	0.0000 (5)	−0.0013 (5)
N3	0.0229 (6)	0.0399 (7)	0.0319 (8)	−0.0047 (6)	−0.0020 (6)	0.0091 (6)
N4	0.0267 (6)	0.0389 (7)	0.0287 (8)	0.0053 (6)	0.0054 (6)	0.0065 (6)
C1	0.0167 (7)	0.0287 (7)	0.0231 (8)	−0.0035 (6)	0.0041 (6)	−0.0004 (6)
C2	0.0154 (6)	0.0286 (7)	0.0241 (9)	0.0052 (6)	−0.0007 (6)	−0.0013 (6)
C3	0.0117 (6)	0.0210 (6)	0.0210 (8)	−0.0002 (5)	0.0014 (5)	0.0041 (5)
C4	0.0101 (6)	0.0217 (6)	0.0211 (8)	−0.0006 (5)	0.0001 (5)	0.0045 (5)
C5	0.0124 (6)	0.0268 (7)	0.0208 (8)	−0.0011 (5)	−0.0006 (6)	0.0008 (5)
C6	0.0131 (6)	0.0249 (7)	0.0229 (8)	0.0011 (5)	0.0019 (6)	0.0012 (6)
C7	0.0137 (6)	0.0285 (7)	0.0223 (8)	0.0013 (5)	0.0007 (6)	−0.0007 (6)
C8	0.0094 (6)	0.0300 (7)	0.0350 (9)	−0.0019 (5)	−0.0030 (6)	0.0081 (6)
C9	0.0153 (6)	0.0262 (7)	0.0256 (9)	−0.0038 (5)	−0.0042 (6)	0.0051 (6)
C10	0.0107 (6)	0.0284 (7)	0.0324 (9)	0.0028 (5)	0.0043 (6)	0.0064 (6)

N1—C3	1.4357 (17)	C4—C6	1.3911 (19)
N1—C7	1.4648 (18)	C5—H1c5	0.96
N1—H1	0.935 (18)	C5—H2c5	0.96
N2—C4	1.4016 (16)	C6—C10	1.3963 (18)
N2—C5	1.4457 (19)	C6—H1c6	0.96
N2—H2	0.889 (18)	C7—H1c7	0.96
N3—C1	1.146 (2)	C7—H2c7	0.96
N4—C2	1.144 (2)	C8—C9	1.384 (2)
C1—C7	1.479 (2)	C8—C10	1.379 (2)
C2—C5	1.480 (2)	C8—H1c8	0.96
C3—C4	1.404 (2)	C9—H1c9	0.96
C3—C9	1.3908 (18)	C10—H1c10	0.96
C3—N1—C7	112.49 (10)	H1c5—C5—H2c5	105.18
C3—N1—H1	108.1 (10)	C4—C6—C10	120.20 (14)
C7—N1—H1	109.8 (11)	C4—C6—H1c6	119.9
C4—N2—C5	119.29 (11)	C10—C6—H1c6	119.9
C4—N2—H2	113.2 (11)	N1—C7—C1	113.27 (11)
C5—N2—H2	114.8 (12)	N1—C7—H1c7	109.47
N3—C1—C7	177.27 (15)	N1—C7—H2c7	109.47
N4—C2—C5	176.55 (16)	C1—C7—H1c7	109.47
N1—C3—C4	118.67 (11)	C1—C7—H2c7	109.47
N1—C3—C9	121.29 (13)	H1c7—C7—H2c7	105.38
C4—C3—C9	120.04 (12)	C9—C8—C10	119.55 (13)
N2—C4—C3	118.05 (12)	C9—C8—H1c8	120.22
N2—C4—C6	123.02 (13)	C10—C8—H1c8	120.22
C3—C4—C6	118.90 (12)	C3—C9—C8	120.63 (14)
N2—C5—C2	113.45 (11)	C3—C9—H1c9	119.69
N2—C5—H1c5	109.47	C8—C9—H1c9	119.69
N2—C5—H2c5	109.47	C6—C10—C8	120.65 (13)
C2—C5—H1c5	109.47	C6—C10—H1c10	119.67
C2—C5—H2c5	109.47	C8—C10—H1c10	119.67

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4i	0.935 (18)	2.202 (19)	3.0946 (19)	159.2 (16)
N2—H2···N1	0.889 (18)	2.427 (18)	2.7524 (18)	102.0 (13)
N2—H2···N1ii	0.889 (18)	2.494 (17)	3.2536 (16)	143.8 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N4i	0.935 (18)	2.202 (19)	3.0946 (19)	159.2 (16)
N2—H2⋯N1	0.889 (18)	2.427 (18)	2.7524 (18)	102.0 (13)
N2—H2⋯N1ii	0.889 (18)	2.494 (17)	3.2536 (16)	143.8 (15)

Symmetry codes: (i) ; (ii) .