Diethyl 2-(4-nitro­phenyl)­malonate forms a hydrogen-bonded chain of rings

Molecules of the title compound, C₁₃H₁₅NO₆, are linked by two C—H...O hydrogen bonds [H...O = 2.32 and 2.46 Å, C...O = 3.306 (2) and 3.393 (2) Å, and C—H...O = 171 and 156°] into a C(4)C(7)[R₃²(11)] chain of rings.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.125
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

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Computing details

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXS97; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Diethyl 2-(4-nitrophenyl)malonate

Crystal data

C13H15NO6	F(000) = 592
Mr = 281.26	Dx = 1.355 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3150 reflections
a = 11.9275 (6) Å	θ = 2.9–27.5°
b = 13.8407 (8) Å	µ = 0.11 mm^−1
c = 8.4595 (3) Å	T = 120 K
β = 99.192 (3)°	Block, colourless
V = 1378.60 (12) Å^3	0.35 × 0.20 × 0.08 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	3150 independent reflections
Radiation source: rotating anode	2007 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.067
φ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (SORTAV; Blessing 1995, 1997)	h = −12→15
Tmin = 0.967, Tmax = 0.991	k = −17→17
14747 measured reflections	l = −10→8

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)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0643P)^2 + 0.0884P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
3150 reflections	Δρmax = 0.30 e Å^−3
184 parameters	Δρmin = −0.32 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: 0.023 (3)

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

	x	y	z	Uiso*/Ueq
C1	0.26206 (15)	0.70841 (13)	0.0045 (2)	0.0278 (4)
C2	0.31247 (15)	0.78599 (13)	0.0895 (2)	0.0304 (4)
C3	0.42206 (15)	0.77511 (13)	0.1707 (2)	0.0272 (4)
C4	0.47936 (14)	0.68809 (12)	0.16643 (19)	0.0223 (4)
C5	0.42446 (15)	0.61054 (13)	0.0833 (2)	0.0271 (4)
C6	0.31552 (15)	0.62012 (13)	0.0003 (2)	0.0288 (4)
N1	0.14715 (14)	0.71995 (13)	−0.0862 (2)	0.0378 (4)
O11	0.10571 (12)	0.65304 (12)	−0.1696 (2)	0.0525 (4)
O12	0.09727 (13)	0.79570 (13)	−0.0729 (2)	0.0643 (5)
C7	0.60129 (14)	0.68116 (12)	0.24883 (19)	0.0231 (4)
C8	0.62259 (14)	0.59399 (13)	0.3596 (2)	0.0246 (4)
C9	0.68408 (14)	0.67088 (12)	0.1294 (2)	0.0236 (4)
O81	0.63993 (11)	0.62046 (9)	0.51212 (14)	0.0323 (3)
O82	0.62378 (12)	0.51227 (9)	0.31328 (15)	0.0384 (4)
C81	0.66937 (19)	0.54315 (15)	0.6290 (2)	0.0398 (5)
C82	0.7935 (2)	0.52559 (17)	0.6564 (3)	0.0522 (6)
O91	0.78551 (10)	0.70414 (9)	0.19546 (14)	0.0282 (3)
O92	0.66166 (10)	0.63559 (9)	−0.00140 (13)	0.0271 (3)
C91	0.87722 (15)	0.69521 (14)	0.0998 (2)	0.0330 (5)
C92	0.92740 (18)	0.59653 (16)	0.1161 (3)	0.0449 (5)
H2	0.2731	0.8455	0.0923	0.036*
H3	0.4585	0.8278	0.2299	0.033*
H5	0.4623	0.5501	0.0834	0.032*
H6	0.2784	0.5674	−0.0582	0.035*
H7	0.6207	0.7411	0.3133	0.028*
H81A	0.6291	0.4832	0.5894	0.048*
H81B	0.6447	0.5612	0.7313	0.048*
H82A	0.8177	0.5069	0.5553	0.078*
H82B	0.8116	0.4736	0.7349	0.078*
H82C	0.8333	0.5847	0.6971	0.078*
H91A	0.9369	0.7437	0.1361	0.040*
H91B	0.8470	0.7082	−0.0141	0.040*
H92A	0.9520	0.5819	0.2297	0.067*
H92B	0.9929	0.5936	0.0595	0.067*
H92C	0.8704	0.5492	0.0698	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0240 (9)	0.0303 (10)	0.0285 (9)	−0.0002 (8)	0.0021 (7)	0.0043 (8)
C2	0.0304 (10)	0.0221 (10)	0.0390 (11)	0.0035 (8)	0.0066 (8)	0.0012 (8)
C3	0.0310 (10)	0.0206 (9)	0.0298 (10)	−0.0017 (7)	0.0041 (7)	−0.0024 (7)
C4	0.0273 (9)	0.0212 (9)	0.0191 (8)	0.0002 (7)	0.0055 (6)	0.0016 (6)
C5	0.0325 (10)	0.0213 (9)	0.0270 (9)	0.0030 (8)	0.0034 (7)	−0.0014 (7)
C6	0.0311 (10)	0.0249 (10)	0.0294 (10)	−0.0038 (8)	0.0020 (7)	−0.0026 (7)
N1	0.0310 (9)	0.0343 (10)	0.0458 (10)	0.0006 (8)	−0.0006 (7)	0.0072 (8)
O11	0.0390 (9)	0.0486 (10)	0.0629 (10)	−0.0046 (7)	−0.0128 (7)	−0.0064 (8)
O12	0.0396 (9)	0.0472 (11)	0.0973 (14)	0.0120 (8)	−0.0155 (8)	−0.0043 (9)
C7	0.0279 (9)	0.0197 (9)	0.0211 (9)	0.0001 (7)	0.0018 (7)	−0.0022 (7)
C8	0.0258 (10)	0.0245 (10)	0.0231 (9)	0.0008 (7)	0.0024 (7)	−0.0003 (7)
C9	0.0268 (10)	0.0189 (9)	0.0236 (9)	0.0009 (7)	−0.0004 (7)	0.0029 (7)
O81	0.0498 (8)	0.0274 (7)	0.0195 (6)	0.0096 (6)	0.0047 (5)	0.0020 (5)
O82	0.0604 (9)	0.0224 (7)	0.0290 (7)	0.0011 (6)	−0.0027 (6)	0.0000 (6)
C81	0.0634 (14)	0.0335 (11)	0.0224 (10)	0.0165 (10)	0.0070 (9)	0.0086 (8)
C82	0.0610 (15)	0.0388 (13)	0.0491 (13)	0.0059 (11)	−0.0152 (11)	0.0073 (10)
O91	0.0243 (7)	0.0321 (7)	0.0273 (7)	−0.0024 (5)	0.0014 (5)	−0.0022 (5)
O92	0.0315 (7)	0.0280 (7)	0.0213 (7)	−0.0005 (5)	0.0025 (5)	−0.0025 (5)
C91	0.0257 (10)	0.0382 (12)	0.0356 (11)	−0.0039 (8)	0.0070 (7)	0.0008 (8)
C92	0.0352 (12)	0.0402 (13)	0.0599 (14)	0.0032 (10)	0.0098 (9)	−0.0047 (10)

Geometric parameters (Å, º)

C1—C2	1.376 (3)	C8—O81	1.325 (2)
C1—C6	1.382 (3)	O81—C81	1.461 (2)
C1—N1	1.469 (2)	C81—C82	1.482 (3)
C2—C3	1.384 (3)	C81—H81A	0.99
C2—H2	0.95	C81—H81B	0.99
C3—C4	1.388 (2)	C82—H82A	0.98
C3—H3	0.95	C82—H82B	0.98
C4—C5	1.389 (2)	C82—H82C	0.98
C4—C7	1.512 (2)	C9—O92	1.200 (2)
C5—C6	1.381 (3)	C9—O91	1.331 (2)
C5—H5	0.95	O91—C91	1.466 (2)
C6—H6	0.95	C91—C92	1.489 (3)
N1—O12	1.220 (2)	C91—H91A	0.99
N1—O11	1.220 (2)	C91—H91B	0.99
C7—C8	1.524 (2)	C92—H92A	0.98
C7—C9	1.528 (2)	C92—H92B	0.98
C7—H7	1.00	C92—H92C	0.98
C8—O82	1.198 (2)
C2—C1—C6	122.62 (17)	C8—O81—C81	116.07 (14)
C2—C1—N1	118.79 (16)	O81—C81—C82	110.62 (17)
C6—C1—N1	118.59 (16)	O81—C81—H81A	109.5
C1—C2—C3	118.26 (16)	C82—C81—H81A	109.5
C1—C2—H2	120.9	O81—C81—H81B	109.5
C3—C2—H2	120.9	C82—C81—H81B	109.5
C2—C3—C4	120.76 (16)	H81A—C81—H81B	108.1
C2—C3—H3	119.6	C81—C82—H82A	109.5
C4—C3—H3	119.6	C81—C82—H82B	109.5
C3—C4—C5	119.30 (16)	H82A—C82—H82B	109.5
C3—C4—C7	118.97 (15)	C81—C82—H82C	109.5
C5—C4—C7	121.70 (15)	H82A—C82—H82C	109.5
C6—C5—C4	120.83 (16)	H82B—C82—H82C	109.5
C6—C5—H5	119.6	O92—C9—O91	125.55 (15)
C4—C5—H5	119.6	O92—C9—C7	125.12 (15)
C5—C6—C1	118.18 (16)	O91—C9—C7	109.29 (13)
C5—C6—H6	120.9	C9—O91—C91	116.59 (13)
C1—C6—H6	120.9	O91—C91—C92	110.53 (15)
O12—N1—O11	123.19 (17)	O91—C91—H91A	109.5
O12—N1—C1	118.27 (17)	C92—C91—H91A	109.5
O11—N1—C1	118.54 (17)	O91—C91—H91B	109.5
C4—C7—C8	112.79 (14)	C92—C91—H91B	109.5
C4—C7—C9	112.13 (13)	H91A—C91—H91B	108.1
C8—C7—C9	105.72 (13)	C91—C92—H92A	109.5
C4—C7—H7	108.7	C91—C92—H92B	109.5
C8—C7—H7	108.7	H92A—C92—H92B	109.5
C9—C7—H7	108.7	C91—C92—H92C	109.5
O82—C8—O81	124.86 (15)	H92A—C92—H92C	109.5
O82—C8—C7	123.76 (15)	H92B—C92—H92C	109.5
O81—C8—C7	111.38 (14)
C6—C1—C2—C3	1.4 (3)	C3—C4—C7—C9	−110.83 (17)
N1—C1—C2—C3	−178.11 (16)	C5—C4—C7—C9	67.4 (2)
C1—C2—C3—C4	−0.1 (3)	C4—C7—C8—O82	71.3 (2)
C2—C3—C4—C5	−1.8 (3)	C9—C7—C8—O82	−51.5 (2)
C2—C3—C4—C7	176.49 (15)	C4—C7—C8—O81	−108.98 (16)
C3—C4—C5—C6	2.4 (3)	C9—C7—C8—O81	128.15 (15)
C7—C4—C5—C6	−175.85 (16)	O82—C8—O81—C81	3.9 (3)
C4—C5—C6—C1	−1.1 (3)	C7—C8—O81—C81	−175.76 (15)
C2—C1—C6—C5	−0.9 (3)	C8—O81—C81—C82	86.5 (2)
N1—C1—C6—C5	178.67 (16)	C4—C7—C9—O92	−27.5 (2)
C2—C1—N1—O12	−5.6 (3)	C8—C7—C9—O92	95.81 (19)
C6—C1—N1—O12	174.88 (19)	C4—C7—C9—O91	154.61 (14)
C2—C1—N1—O11	175.30 (17)	C8—C7—C9—O91	−82.10 (16)
C6—C1—N1—O11	−4.3 (3)	O92—C9—O91—C91	−0.9 (2)
C3—C4—C7—C8	129.95 (16)	C7—C9—O91—C91	176.99 (13)
C5—C4—C7—C8	−51.8 (2)	C9—O91—C91—C92	−82.42 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O92^i	1.00	2.32	3.306 (2)	171
C81—H81B···O92^ii	0.99	2.46	3.393 (2)	156

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, y, z+1.