N-(2-Nitro-4-propoxyphen­yl)acetamide

The title compound, C₁₁H₁₄N₂O₄, has an almost planar mol­ecule, whose conformation is stabilized by an intra­molecular N—H...O hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.038
• wR factor = 0.105
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

N-(2-Nitro-4-propoxyphenyl)acetamide

Crystal data

C11H14N2O4	F(000) = 504
Mr = 238.24	Dx = 1.388 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15729 reflections
a = 16.9055 (15) Å	θ = 3.9–27.0°
b = 4.0057 (2) Å	µ = 0.11 mm^−1
c = 18.0989 (16) Å	T = 173 K
β = 111.490 (7)°	Plate, orange
V = 1140.42 (15) Å^3	0.31 × 0.26 × 0.08 mm
Z = 4

Data collection

Stoe IPDSII two-circle diffractometer	2090 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
Graphite monochromator	θmax = 26.9°, θmin = 3.8°
ω scans	h = −21→21
15998 measured reflections	k = −5→5
2437 independent reflections	l = −22→23

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0566P)^2 + 0.2987P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2437 reflections	Δρmax = 0.27 e Å^−3
160 parameters	Δρmin = −0.21 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: 0.015 (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	0.19540 (8)	0.6496 (3)	0.32679 (7)	0.0241 (3)
C2	0.18324 (7)	0.7025 (3)	0.24623 (7)	0.0226 (3)
C3	0.24008 (7)	0.5858 (3)	0.21179 (7)	0.0225 (3)
H3	0.2296	0.6262	0.1573	0.027*
C4	0.31185 (8)	0.4108 (3)	0.25839 (7)	0.0234 (3)
C5	0.32464 (8)	0.3487 (4)	0.33828 (7)	0.0278 (3)
H5	0.3732	0.2256	0.3702	0.033*
C6	0.26813 (8)	0.4630 (4)	0.37135 (7)	0.0277 (3)
H6	0.2784	0.4151	0.4255	0.033*
N1	0.13989 (7)	0.7723 (3)	0.36209 (6)	0.0283 (3)
H1	0.0892 (13)	0.843 (5)	0.3270 (12)	0.048 (5)*
C11	0.15802 (8)	0.8339 (3)	0.44170 (7)	0.0270 (3)
O11	0.22646 (7)	0.7748 (3)	0.49371 (6)	0.0439 (3)
C12	0.08455 (9)	0.9816 (4)	0.45886 (8)	0.0335 (3)
H12A	0.0423	0.8075	0.4542	0.050*
H12B	0.0585	1.1603	0.4207	0.050*
H12C	0.1051	1.0730	0.5128	0.050*
N2	0.11014 (7)	0.8902 (3)	0.19268 (6)	0.0261 (3)
O21	0.05055 (7)	0.9612 (4)	0.21426 (6)	0.0464 (3)
O22	0.10946 (6)	0.9732 (3)	0.12717 (5)	0.0363 (3)
O4	0.37262 (6)	0.2863 (3)	0.23315 (5)	0.0282 (2)
C41	0.36507 (8)	0.3519 (3)	0.15246 (7)	0.0244 (3)
H41A	0.3534	0.5915	0.1398	0.029*
H41B	0.3180	0.2194	0.1149	0.029*
C42	0.44905 (8)	0.2530 (3)	0.14636 (7)	0.0254 (3)
H42A	0.4614	0.0167	0.1625	0.030*
H42B	0.4951	0.3916	0.1832	0.030*
C43	0.44733 (10)	0.2974 (4)	0.06219 (8)	0.0377 (4)
H43A	0.5019	0.2261	0.0600	0.057*
H43B	0.4376	0.5330	0.0470	0.057*
H43C	0.4015	0.1617	0.0255	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0218 (6)	0.0296 (7)	0.0208 (6)	−0.0027 (5)	0.0078 (5)	−0.0004 (5)
C2	0.0195 (6)	0.0260 (6)	0.0198 (5)	−0.0017 (5)	0.0041 (4)	−0.0002 (5)
C3	0.0223 (6)	0.0258 (6)	0.0187 (5)	−0.0026 (5)	0.0068 (5)	−0.0001 (5)
C4	0.0216 (6)	0.0250 (6)	0.0244 (6)	−0.0011 (5)	0.0091 (5)	0.0000 (5)
C5	0.0244 (6)	0.0335 (7)	0.0236 (6)	0.0031 (5)	0.0066 (5)	0.0044 (5)
C6	0.0260 (6)	0.0361 (7)	0.0205 (6)	0.0010 (5)	0.0077 (5)	0.0043 (5)
N1	0.0228 (5)	0.0431 (7)	0.0189 (5)	0.0032 (5)	0.0074 (4)	0.0006 (5)
C11	0.0295 (7)	0.0297 (7)	0.0220 (6)	−0.0036 (5)	0.0099 (5)	−0.0018 (5)
O11	0.0350 (6)	0.0653 (8)	0.0242 (5)	0.0089 (5)	0.0023 (4)	−0.0082 (5)
C12	0.0363 (7)	0.0399 (8)	0.0272 (6)	0.0034 (6)	0.0151 (6)	−0.0023 (6)
N2	0.0232 (5)	0.0335 (6)	0.0196 (5)	0.0027 (5)	0.0055 (4)	−0.0007 (4)
O21	0.0298 (5)	0.0818 (9)	0.0295 (5)	0.0230 (6)	0.0130 (4)	0.0107 (5)
O22	0.0374 (6)	0.0484 (6)	0.0234 (5)	0.0121 (5)	0.0114 (4)	0.0097 (4)
O4	0.0261 (5)	0.0370 (5)	0.0237 (4)	0.0078 (4)	0.0116 (4)	0.0058 (4)
C41	0.0257 (6)	0.0265 (6)	0.0214 (6)	0.0013 (5)	0.0092 (5)	0.0018 (5)
C42	0.0247 (6)	0.0274 (6)	0.0241 (6)	−0.0004 (5)	0.0091 (5)	−0.0018 (5)
C43	0.0417 (8)	0.0474 (9)	0.0288 (7)	0.0081 (7)	0.0186 (6)	0.0031 (6)

Geometric parameters (Å, º)

C1—N1	1.4036 (17)	C12—H12A	0.9800
C1—C2	1.4118 (17)	C12—H12B	0.9800
C1—C6	1.4121 (18)	C12—H12C	0.9800
C2—C3	1.4032 (18)	N2—O22	1.2274 (14)
C2—N2	1.4678 (16)	N2—O21	1.2396 (15)
C3—C4	1.3876 (17)	O4—C41	1.4428 (14)
C3—H3	0.9500	C41—C42	1.5164 (17)
C4—O4	1.3626 (15)	C41—H41A	0.9900
C4—C5	1.4036 (17)	C41—H41B	0.9900
C5—C6	1.3782 (19)	C42—C43	1.5233 (18)
C5—H5	0.9500	C42—H42A	0.9900
C6—H6	0.9500	C42—H42B	0.9900
N1—C11	1.3810 (16)	C43—H43A	0.9800
N1—H1	0.91 (2)	C43—H43B	0.9800
C11—O11	1.2177 (16)	C43—H43C	0.9800
C11—C12	1.5072 (19)
N1—C1—C2	123.29 (12)	H12A—C12—H12B	109.5
N1—C1—C6	120.85 (11)	C11—C12—H12C	109.5
C2—C1—C6	115.86 (12)	H12A—C12—H12C	109.5
C3—C2—C1	122.98 (11)	H12B—C12—H12C	109.5
C3—C2—N2	115.16 (10)	O22—N2—O21	121.42 (11)
C1—C2—N2	121.85 (11)	O22—N2—C2	118.96 (11)
C4—C3—C2	119.14 (11)	O21—N2—C2	119.62 (11)
C4—C3—H3	120.4	C4—O4—C41	118.34 (9)
C2—C3—H3	120.4	O4—C41—C42	106.75 (10)
O4—C4—C3	125.45 (11)	O4—C41—H41A	110.4
O4—C4—C5	115.46 (11)	C42—C41—H41A	110.4
C3—C4—C5	119.08 (12)	O4—C41—H41B	110.4
C6—C5—C4	121.25 (12)	C42—C41—H41B	110.4
C6—C5—H5	119.4	H41A—C41—H41B	108.6
C4—C5—H5	119.4	C41—C42—C43	111.53 (11)
C5—C6—C1	121.66 (12)	C41—C42—H42A	109.3
C5—C6—H6	119.2	C43—C42—H42A	109.3
C1—C6—H6	119.2	C41—C42—H42B	109.3
C11—N1—C1	127.42 (11)	C43—C42—H42B	109.3
C11—N1—H1	117.8 (12)	H42A—C42—H42B	108.0
C1—N1—H1	114.2 (12)	C42—C43—H43A	109.5
O11—C11—N1	123.83 (13)	C42—C43—H43B	109.5
O11—C11—C12	122.58 (12)	H43A—C43—H43B	109.5
N1—C11—C12	113.60 (11)	C42—C43—H43C	109.5
C11—C12—H12A	109.5	H43A—C43—H43C	109.5
C11—C12—H12B	109.5	H43B—C43—H43C	109.5
N1—C1—C2—C3	178.43 (12)	C2—C1—N1—C11	−156.72 (13)
C6—C1—C2—C3	−1.42 (19)	C6—C1—N1—C11	23.1 (2)
N1—C1—C2—N2	−0.5 (2)	C1—N1—C11—O11	−3.0 (2)
C6—C1—C2—N2	179.64 (12)	C1—N1—C11—C12	177.17 (13)
C1—C2—C3—C4	−0.14 (19)	C3—C2—N2—O22	−10.23 (17)
N2—C2—C3—C4	178.87 (11)	C1—C2—N2—O22	168.79 (12)
C2—C3—C4—O4	−179.33 (12)	C3—C2—N2—O21	169.64 (12)
C2—C3—C4—C5	1.41 (19)	C1—C2—N2—O21	−11.35 (19)
O4—C4—C5—C6	179.57 (12)	C3—C4—O4—C41	3.01 (19)
C3—C4—C5—C6	−1.1 (2)	C5—C4—O4—C41	−177.70 (11)
C4—C5—C6—C1	−0.5 (2)	C4—O4—C41—C42	167.94 (11)
N1—C1—C6—C5	−178.11 (13)	O4—C41—C42—C43	177.53 (11)
C2—C1—C6—C5	1.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O21	0.91 (2)	1.96 (2)	2.6554 (15)	132.4 (17)