N,N′-Bis(2-nitro­benzylidene)ethyl­ene­diamine

The mol­ecule of the title compound, C₆H₁₄N₄O₄, possesses a crystallographically imposed centre of symmetry. In the crystal packing, the mol­ecules are linked via weak inter­molecular C—H...O hydrogen bonds into a sheet-like structure parallel to the (10) plane.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.054
• wR factor = 0.154
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.01

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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

(I)

Crystal data

C16H14N4O4	F(000) = 340
Mr = 326.31	Dx = 1.404 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1412 reflections
a = 7.4255 (10) Å	θ = 2.6–24.1°
b = 15.497 (2) Å	µ = 0.10 mm^−1
c = 7.0806 (10) Å	T = 292 K
β = 108.648 (2)°	Block, yellow
V = 772.00 (18) Å^3	0.30 × 0.20 × 0.20 mm
Z = 2

Data collection

Siemens SMART CCD area-detector diffractometer	1671 independent reflections
Radiation source: fine-focus sealed tube	1319 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 27.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→7
Tmin = 0.975, Tmax = 0.979	k = −19→19
4450 measured reflections	l = −9→8

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.154	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0693P)^2 + 0.2476P] where P = (Fo^2 + 2Fc^2)/3
1671 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4457 (3)	0.28932 (11)	0.1642 (3)	0.0438 (4)
C2	0.3612 (3)	0.20876 (12)	0.1388 (3)	0.0528 (5)
H2	0.2295	0.2034	0.0943	0.063*
C3	0.4756 (3)	0.13652 (12)	0.1805 (3)	0.0559 (5)
H3	0.4210	0.0819	0.1655	0.067*
C4	0.6700 (3)	0.14508 (12)	0.2444 (3)	0.0540 (5)
H4	0.7467	0.0962	0.2726	0.065*
C5	0.7519 (3)	0.22584 (12)	0.2667 (3)	0.0498 (5)
H5	0.8836	0.2305	0.3082	0.060*
C6	0.6421 (3)	0.30075 (11)	0.2286 (2)	0.0411 (4)
C7	0.7422 (3)	0.38503 (11)	0.2524 (3)	0.0448 (4)
H7	0.6896	0.4302	0.1660	0.054*
C8	0.9887 (3)	0.47980 (12)	0.4000 (3)	0.0531 (5)
H8A	0.9122	0.5170	0.2945	0.064*
H8B	1.1124	0.4730	0.3827	0.064*
N1	0.3186 (2)	0.36442 (11)	0.1251 (3)	0.0579 (5)
N2	0.8969 (2)	0.39546 (10)	0.3881 (2)	0.0516 (5)
O1	0.1547 (3)	0.35509 (13)	0.0299 (4)	0.1215 (9)
O2	0.3804 (2)	0.43381 (11)	0.1914 (3)	0.0907 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0482 (10)	0.0365 (9)	0.0439 (9)	−0.0006 (7)	0.0107 (8)	−0.0016 (7)
C2	0.0529 (11)	0.0458 (11)	0.0557 (11)	−0.0109 (8)	0.0115 (9)	−0.0034 (8)
C3	0.0746 (14)	0.0340 (10)	0.0578 (11)	−0.0120 (9)	0.0194 (10)	−0.0041 (8)
C4	0.0711 (14)	0.0349 (10)	0.0570 (11)	0.0067 (9)	0.0217 (10)	0.0004 (8)
C5	0.0511 (11)	0.0408 (10)	0.0565 (11)	0.0019 (8)	0.0160 (9)	−0.0006 (8)
C6	0.0495 (10)	0.0347 (9)	0.0378 (8)	−0.0030 (7)	0.0121 (7)	−0.0024 (6)
C7	0.0488 (10)	0.0343 (9)	0.0504 (10)	−0.0008 (7)	0.0145 (8)	0.0013 (7)
C8	0.0461 (10)	0.0412 (10)	0.0692 (12)	−0.0092 (8)	0.0145 (9)	0.0025 (9)
N1	0.0493 (10)	0.0447 (10)	0.0737 (11)	0.0005 (7)	0.0112 (8)	−0.0025 (8)
N2	0.0477 (9)	0.0382 (9)	0.0652 (10)	−0.0074 (6)	0.0131 (8)	0.0013 (7)
O1	0.0536 (11)	0.0763 (13)	0.195 (2)	0.0077 (9)	−0.0167 (12)	−0.0165 (14)
O2	0.0697 (11)	0.0418 (9)	0.1533 (18)	0.0035 (7)	0.0251 (11)	−0.0137 (10)

Geometric parameters (Å, º)

C1—C2	1.383 (2)	C5—H5	0.9300
C1—C6	1.393 (3)	C6—C7	1.486 (2)
C1—N1	1.468 (2)	C7—N2	1.250 (2)
C2—C3	1.379 (3)	C7—H7	0.9300
C2—H2	0.9300	C8—N2	1.464 (2)
C3—C4	1.375 (3)	C8—C8^i	1.508 (4)
C3—H3	0.9300	C8—H8A	0.9700
C4—C5	1.378 (3)	C8—H8B	0.9700
C4—H4	0.9300	N1—O1	1.196 (2)
C5—C6	1.394 (2)	N1—O2	1.204 (2)
C2—C1—C6	122.78 (17)	C1—C6—C7	125.63 (16)
C2—C1—N1	116.97 (17)	C5—C6—C7	118.00 (16)
C6—C1—N1	120.24 (15)	N2—C7—C6	120.30 (16)
C3—C2—C1	118.82 (18)	N2—C7—H7	119.8
C3—C2—H2	120.6	C6—C7—H7	119.8
C1—C2—H2	120.6	N2—C8—C8^i	109.52 (19)
C4—C3—C2	120.16 (17)	N2—C8—H8A	109.8
C4—C3—H3	119.9	C8^i—C8—H8A	109.8
C2—C3—H3	119.9	N2—C8—H8B	109.8
C3—C4—C5	120.24 (18)	C8^i—C8—H8B	109.8
C3—C4—H4	119.9	H8A—C8—H8B	108.2
C5—C4—H4	119.9	O1—N1—O2	121.30 (19)
C4—C5—C6	121.66 (18)	O1—N1—C1	119.16 (17)
C4—C5—H5	119.2	O2—N1—C1	119.53 (17)
C6—C5—H5	119.2	C7—N2—C8	117.13 (16)
C1—C6—C5	116.33 (16)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2	0.93	2.36	2.689 (3)	101
C5—H5···O1^ii	0.93	2.50	3.229 (3)	135

Symmetry code: (ii) x+1, −y+1/2, z+1/2.