p-Nitro­phenyl­male­imide

The title compound, C₁₀H₆N₂O₄, belongs to a series of N-aryl­male­imides. These N-substituted male­imides can be used as photo-initiators for free-radical polymerization. The mol­ecule has crystallographic twofold rotation symmetry. The dihedral angle between the planes of the benzene and imide rings is 42.98 (5)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.030
• wR factor = 0.084
• Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT764_ALERT_4_C Overcomplete CIF Bond list Detected (Rep/Expd) .       1.17 Ratio

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 SDP (Frenz, 1978); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C10H6N2O4	F(000) = 448
Mr = 218.17	Dx = 1.543 Mg m^−3
Monoclinic, C2/c	Melting point: 436(1) K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 10.535 (2) Å	Cell parameters from 25 reflections
b = 11.624 (3) Å	θ = 8–16°
c = 8.148 (2) Å	µ = 0.12 mm^−1
β = 109.69 (3)°	T = 293 K
V = 939.5 (4) Å^3	Prism, colourless
Z = 4	0.18 × 0.15 × 0.08 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.017
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.7°
Graphite monochromator	h = 0→12
ω/2θ scans	k = −13→0
870 measured reflections	l = −9→9
824 independent reflections	3 standard reflections every 120 min
738 reflections with I > 2σ(I)	intensity decay: 1.2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.085	w = 1/[σ^2(Fo^2) + (0.0429P)^2 + 0.4529P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
824 reflections	Δρmax = 0.14 e Å^−3
76 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0169 (18)

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.

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

	x	y	z	Uiso*/Ueq
N1	0.5000	0.21145 (13)	0.2500	0.0394 (4)
N2	0.5000	−0.27159 (14)	0.2500	0.0426 (4)
C4	0.5000	0.08902 (15)	0.2500	0.0345 (4)
C1	0.5000	−0.14578 (15)	0.2500	0.0359 (4)
C3	0.39783 (13)	0.03000 (11)	0.12627 (18)	0.0407 (4)
H3	0.3294	0.0703	0.0438	0.049*
O2	0.43544 (12)	−0.32156 (9)	0.11594 (15)	0.0611 (4)
C2	0.39760 (13)	−0.08862 (12)	0.12539 (17)	0.0405 (4)
H2	0.3297	−0.1292	0.0424	0.049*
O1	0.27411 (10)	0.24654 (10)	0.20227 (15)	0.0572 (4)
C5	0.38614 (15)	0.28100 (12)	0.22655 (18)	0.0441 (4)
C6	0.43556 (17)	0.40155 (13)	0.2380 (2)	0.0566 (4)
H6	0.3828	0.4669	0.2293	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0392 (8)	0.0297 (8)	0.0479 (9)	0.000	0.0128 (7)	0.000
N2	0.0480 (9)	0.0326 (9)	0.0474 (10)	0.000	0.0164 (8)	0.000
C4	0.0349 (9)	0.0311 (9)	0.0402 (9)	0.000	0.0161 (8)	0.000
C1	0.0399 (10)	0.0299 (9)	0.0408 (10)	0.000	0.0175 (8)	0.000
C3	0.0364 (7)	0.0370 (8)	0.0431 (8)	0.0024 (5)	0.0062 (6)	0.0039 (6)
O2	0.0801 (8)	0.0380 (6)	0.0563 (7)	−0.0050 (5)	0.0113 (6)	−0.0102 (5)
C2	0.0374 (7)	0.0370 (7)	0.0428 (7)	−0.0048 (6)	0.0078 (6)	−0.0020 (6)
O1	0.0444 (6)	0.0538 (7)	0.0729 (8)	0.0088 (5)	0.0189 (5)	−0.0050 (5)
C5	0.0481 (8)	0.0384 (8)	0.0430 (8)	0.0079 (6)	0.0115 (6)	−0.0009 (6)
C6	0.0698 (9)	0.0341 (8)	0.0570 (9)	0.0086 (7)	0.0098 (8)	−0.0023 (7)

Geometric parameters (Å, º)

N1—C5^i	1.4052 (17)	C1—C2	1.3777 (16)
N1—C5	1.4052 (17)	C3—C2	1.379 (2)
N1—C4	1.423 (2)	C3—H3	0.930
N2—O2	1.2217 (13)	C2—H2	0.930
N2—O2^i	1.2217 (13)	O1—C5	1.1979 (18)
N2—C1	1.462 (2)	C5—C6	1.487 (2)
C4—C3	1.3835 (16)	C6—C6^i	1.305 (3)
C4—C3^i	1.3835 (16)	C6—H6	0.930
C1—C2^i	1.3777 (16)
C5^i—N1—C5	109.75 (16)	C2—C3—C4	119.94 (13)
C5^i—N1—C4	125.12 (8)	C2—C3—H3	120.0
C5—N1—C4	125.12 (8)	C4—C3—H3	120.0
O2—N2—O2^i	123.22 (17)	C1—C2—C3	118.61 (12)
O2—N2—C1	118.39 (8)	C1—C2—H2	120.7
O2^i—N2—C1	118.39 (8)	C3—C2—H2	120.7
C3—C4—C3^i	120.56 (17)	O1—C5—N1	125.34 (13)
C3—C4—N1	119.72 (9)	O1—C5—C6	129.06 (14)
C3^i—C4—N1	119.72 (9)	N1—C5—C6	105.59 (13)
C2^i—C1—C2	122.33 (17)	C6^i—C6—C5	109.52 (9)
C2^i—C1—N2	118.83 (9)	C6^i—C6—H6	125.2
C2—C1—N2	118.83 (9)	C5—C6—H6	125.2
C5^i—N1—C4—C3	−136.82 (10)	C2^i—C1—C2—C3	−0.20 (9)
C5—N1—C4—C3	43.18 (10)	N2—C1—C2—C3	179.80 (9)
C5^i—N1—C4—C3^i	43.18 (10)	C4—C3—C2—C1	0.39 (18)
C5—N1—C4—C3^i	−136.82 (10)	C5^i—N1—C5—O1	179.43 (17)
O2—N2—C1—C2^i	−159.26 (10)	C4—N1—C5—O1	−0.57 (17)
O2^i—N2—C1—C2^i	20.74 (10)	C5^i—N1—C5—C6	−0.39 (7)
O2—N2—C1—C2	20.74 (10)	C4—N1—C5—C6	179.61 (7)
O2^i—N2—C1—C2	−159.26 (10)	O1—C5—C6—C6^i	−178.66 (18)
C3^i—C4—C3—C2	−0.20 (9)	N1—C5—C6—C6^i	1.2 (2)
N1—C4—C3—C2	179.80 (9)

Symmetry code: (i) −x+1, y, −z+1/2.