4-(4-Nitro-benz-yl)morpholine.

In the title compound, C(11)H(14)N(2)O(3), an inter-molecular inter-action between a nitro group O atom and a neighboring benzene ring helps to stabilize the crystal structure [N⋯centroid = 3.933 (2) Å]. No classical hydrogen bonds are observed in the crystal packing.

Related literature

For the biological activity of 4-(4-nitro­benz­yl)morpholine derivatives, see: Lan et al. (2010 ▶); Bavetsias et al. (2010 ▶). For the synthesis, see: Tsou et al. (2008 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H14N2O3

M = 222.24

Monoclinic,

a = 6.1371 (2) Å

b = 8.2535 (4) Å

c = 21.9867 (9) Å

β = 94.929 (3)°

V = 1109.58 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.40 × 0.30 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 ▶) T min = 0.946, T max = 1.0

6059 measured reflections

2264 independent reflections

1640 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.106

S = 1.04

2264 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005964/vm2073sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005964/vm2073Isup2.hkl

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

C11H14N2O3	F(000) = 472
Mr = 222.24	Dx = 1.330 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 2399 reflections
a = 6.1371 (2) Å	θ = 3.1–29.2°
b = 8.2535 (4) Å	µ = 0.10 mm−1
c = 21.9867 (9) Å	T = 293 K
β = 94.929 (3)°	Block, yellow
V = 1109.58 (8) Å3	0.40 × 0.30 × 0.25 mm
Z = 4

Oxford Diffraction Xcalibur Eos diffractometer	2264 independent reflections
Radiation source: fine-focus sealed tube	1640 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 3.1°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	k = −8→10
Tmin = 0.946, Tmax = 1.0	l = −25→27
6059 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0423P)2 + 0.1325P] where P = (Fo2 + 2Fc2)/3
2264 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
O1	0.40024 (19)	0.31753 (14)	0.53296 (5)	0.0556 (3)
O2	−0.4376 (2)	−0.42771 (17)	0.28701 (7)	0.0751 (4)
O3	−0.1642 (2)	−0.57082 (16)	0.32340 (8)	0.0808 (5)
N1	0.33645 (19)	0.14840 (16)	0.41946 (6)	0.0417 (3)
N2	−0.2491 (2)	−0.44089 (19)	0.30912 (6)	0.0530 (4)
C1	−0.1173 (2)	−0.29260 (19)	0.31894 (7)	0.0413 (4)
C2	−0.2096 (2)	−0.1454 (2)	0.30324 (7)	0.0461 (4)
H2	−0.3521	−0.1392	0.2853	0.055*
C3	−0.0870 (2)	−0.0064 (2)	0.31460 (7)	0.0467 (4)
H3	−0.1484	0.0941	0.3044	0.056*
C4	0.1268 (2)	−0.0148 (2)	0.34109 (7)	0.0420 (4)
C5	0.2166 (2)	−0.1668 (2)	0.35492 (7)	0.0468 (4)
H5	0.3605	−0.1743	0.3718	0.056*
C6	0.0965 (3)	−0.3056 (2)	0.34414 (7)	0.0471 (4)
H6	0.1576	−0.4066	0.3536	0.057*
C7	0.2629 (3)	0.1353 (2)	0.35452 (7)	0.0493 (4)
H7A	0.3893	0.1325	0.3309	0.059*
H7B	0.1771	0.2302	0.3421	0.059*
C8	0.5018 (2)	0.2751 (2)	0.43006 (8)	0.0499 (4)
H8B	0.4409	0.3785	0.4162	0.060*
H8A	0.6256	0.2513	0.4069	0.060*
C9	0.5767 (3)	0.2851 (2)	0.49693 (9)	0.0550 (5)
H9A	0.6451	0.1835	0.5100	0.066*
H9B	0.6853	0.3701	0.5033	0.066*
C10	0.1559 (2)	0.1839 (2)	0.45620 (8)	0.0502 (4)
H10A	0.0466	0.0991	0.4507	0.060*
H10B	0.0879	0.2855	0.4430	0.060*
C11	0.2381 (3)	0.1952 (2)	0.52265 (8)	0.0566 (5)
H11B	0.1165	0.2191	0.5466	0.068*
H11A	0.2992	0.0916	0.5361	0.068*

	U11	U22	U33	U12	U13	U23
O1	0.0660 (7)	0.0481 (7)	0.0523 (7)	−0.0032 (6)	0.0017 (6)	−0.0124 (6)
O2	0.0609 (8)	0.0800 (10)	0.0819 (10)	−0.0136 (7)	−0.0089 (7)	−0.0130 (8)
O3	0.0861 (10)	0.0489 (9)	0.1079 (12)	−0.0023 (7)	0.0107 (8)	0.0089 (8)
N1	0.0422 (7)	0.0462 (8)	0.0372 (7)	−0.0052 (6)	0.0053 (5)	−0.0017 (6)
N2	0.0584 (9)	0.0565 (10)	0.0451 (8)	−0.0045 (7)	0.0101 (7)	−0.0050 (7)
C1	0.0460 (9)	0.0465 (10)	0.0314 (8)	0.0000 (7)	0.0045 (6)	−0.0033 (7)
C2	0.0416 (8)	0.0573 (11)	0.0385 (9)	0.0041 (7)	−0.0026 (7)	−0.0006 (8)
C3	0.0516 (9)	0.0469 (10)	0.0408 (9)	0.0081 (7)	−0.0002 (7)	0.0019 (7)
C4	0.0474 (9)	0.0495 (10)	0.0294 (8)	0.0016 (7)	0.0055 (6)	−0.0017 (7)
C5	0.0399 (8)	0.0607 (12)	0.0394 (9)	0.0034 (8)	−0.0001 (7)	−0.0014 (8)
C6	0.0502 (9)	0.0476 (10)	0.0435 (9)	0.0104 (7)	0.0044 (7)	0.0016 (8)
C7	0.0542 (9)	0.0555 (11)	0.0386 (9)	−0.0047 (8)	0.0065 (7)	0.0027 (8)
C8	0.0463 (9)	0.0492 (11)	0.0546 (11)	−0.0072 (7)	0.0059 (7)	0.0007 (8)
C9	0.0523 (10)	0.0501 (11)	0.0610 (12)	−0.0059 (8)	−0.0047 (8)	−0.0050 (9)
C10	0.0457 (9)	0.0588 (11)	0.0468 (10)	−0.0069 (7)	0.0080 (7)	−0.0067 (8)
C11	0.0632 (11)	0.0609 (12)	0.0472 (10)	−0.0092 (9)	0.0128 (8)	−0.0105 (9)

O1—C9	1.421 (2)	C5—H5	0.9300
O1—C11	1.4218 (19)	C5—C6	1.372 (2)
O2—N2	1.2210 (17)	C6—H6	0.9300
O3—N2	1.2214 (17)	C7—H7A	0.9700
N1—C7	1.4641 (19)	C7—H7B	0.9700
N1—C8	1.4616 (19)	C8—H8B	0.9700
N1—C10	1.456 (2)	C8—H8A	0.9700
N2—C1	1.473 (2)	C8—C9	1.504 (2)
C1—C2	1.372 (2)	C9—H9A	0.9700
C1—C6	1.384 (2)	C9—H9B	0.9700
C2—H2	0.9300	C10—H10A	0.9700
C2—C3	1.383 (2)	C10—H10B	0.9700
C3—H3	0.9300	C10—C11	1.507 (2)
C3—C4	1.3911 (19)	C11—H11B	0.9700
C4—C5	1.393 (2)	C11—H11A	0.9700
C4—C7	1.509 (2)
O1—C9—C8	111.83 (13)	C4—C3—H3	119.6
O1—C9—H9A	109.3	C4—C5—H5	119.4
O1—C9—H9B	109.3	C4—C7—H7A	109.3
O1—C11—C10	111.71 (14)	C4—C7—H7B	109.3
O1—C11—H11B	109.3	C5—C4—C7	119.67 (13)
O1—C11—H11A	109.3	C5—C6—C1	118.75 (15)
O2—N2—O3	123.32 (15)	C5—C6—H6	120.6
O2—N2—C1	118.31 (15)	C6—C1—N2	118.95 (15)
O3—N2—C1	118.38 (14)	C6—C5—C4	121.20 (14)
N1—C7—C4	111.73 (13)	C6—C5—H5	119.4
N1—C7—H7A	109.3	H7A—C7—H7B	107.9
N1—C7—H7B	109.3	C8—N1—C7	111.09 (12)
N1—C8—H8B	109.6	C8—C9—H9A	109.3
N1—C8—H8A	109.6	C8—C9—H9B	109.3
N1—C8—C9	110.15 (14)	H8B—C8—H8A	108.1
N1—C10—H10A	109.6	C9—O1—C11	109.49 (13)
N1—C10—H10B	109.6	C9—C8—H8B	109.6
N1—C10—C11	110.07 (13)	C9—C8—H8A	109.6
C1—C2—H2	120.6	H9A—C9—H9B	107.9
C1—C2—C3	118.87 (14)	C10—N1—C7	111.73 (12)
C1—C6—H6	120.6	C10—N1—C8	108.57 (13)
C2—C1—N2	119.30 (14)	C10—C11—H11B	109.3
C2—C1—C6	121.76 (15)	C10—C11—H11A	109.3
C2—C3—H3	119.6	H10A—C10—H10B	108.2
C2—C3—C4	120.88 (15)	C11—C10—H10A	109.6
C3—C2—H2	120.6	C11—C10—H10B	109.6
C3—C4—C5	118.51 (15)	H11B—C11—H11A	107.9
C3—C4—C7	121.81 (15)