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

Aromatic π-π stacking inter-actions stabilize the crystal structure of the title compound, C(10)H(12)N(2)O(3), the perpendic-ular distance between parallel planes being 3.7721 (8) Å. The morpholine ring adopts a chair comformation.

Related literature

For the biological activity and synthesis of 4-(4-nitro­phen­yl)morpholine derivatives, see: Wang et al. (2010 ▶). For a related structure, see: Yang et al. (2011 ▶).

Experimental

Crystal data

C10H12N2O3

M = 208.22

Orthorhombic,

a = 14.5445 (6) Å

b = 8.3832 (3) Å

c = 16.2341 (6) Å

V = 1979.42 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.35 × 0.33 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 ▶) T min = 0.992, T max = 1.000

4949 measured reflections

2023 independent reflections

1377 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.121

S = 1.03

2023 reflections

184 parameters

All H-atom parameters refined

Δρmax = 0.12 e Å−3

Δρmin = −0.15 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 datablock(s) global, I. DOI: 10.1107/S1600536812012172/kj2195sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012172/kj2195Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012172/kj2195Isup3.cml

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

C10H12N2O3	Dx = 1.397 Mg m−3
Mr = 208.22	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1704 reflections
a = 14.5445 (6) Å	θ = 2.9–29.2°
b = 8.3832 (3) Å	µ = 0.11 mm−1
c = 16.2341 (6) Å	T = 293 K
V = 1979.42 (13) Å3	Block, yellow
Z = 8	0.35 × 0.33 × 0.30 mm
F(000) = 880

Oxford Diffraction Xcalibur Eos diffractometer	2023 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1377 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 2.9°
ω scans	h = −9→18
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	k = −6→10
Tmin = 0.992, Tmax = 1.000	l = −20→12
4949 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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F2) = 0.121	All H-atom parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.050P)2 + 0.3012P] where P = (Fo2 + 2Fc2)/3
2023 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.11977 (11)	0.40333 (15)	0.24876 (9)	0.0774 (5)
O2	0.15361 (12)	−0.3154 (2)	0.66760 (10)	0.0931 (6)
O3	0.09389 (13)	−0.47156 (17)	0.57725 (10)	0.0907 (6)
N1	0.12607 (10)	0.15429 (16)	0.36653 (8)	0.0488 (4)
N2	0.12312 (11)	−0.3406 (2)	0.59853 (11)	0.0642 (5)
C1	0.17590 (18)	0.4172 (3)	0.31932 (13)	0.0674 (6)
H1A	0.2408 (16)	0.378 (2)	0.3051 (12)	0.083 (7)*
H1B	0.1775 (14)	0.531 (2)	0.3339 (12)	0.072 (6)*
C2	0.14099 (17)	0.3205 (2)	0.39042 (13)	0.0587 (5)
H2A	0.1869 (14)	0.327 (2)	0.4354 (12)	0.067 (6)*
H2B	0.0823 (14)	0.367 (2)	0.4102 (12)	0.068 (6)*
C3	0.07821 (15)	0.1361 (3)	0.28780 (11)	0.0567 (5)
H3A	0.0113 (15)	0.159 (2)	0.2958 (12)	0.081 (7)*
H3B	0.0813 (13)	0.028 (2)	0.2697 (11)	0.064 (6)*
C4	0.11879 (17)	0.2413 (2)	0.22354 (13)	0.0647 (5)
H4A	0.0814 (13)	0.237 (2)	0.1743 (13)	0.072 (6)*
H4B	0.1848 (14)	0.205 (2)	0.2122 (12)	0.077 (6)*
C5	0.12154 (11)	0.03660 (19)	0.42504 (10)	0.0440 (4)
C6	0.08684 (14)	−0.1153 (2)	0.40613 (12)	0.0589 (5)
H6	0.0618 (13)	−0.137 (2)	0.3546 (12)	0.069 (6)*
C7	0.08671 (14)	−0.2364 (2)	0.46268 (12)	0.0598 (5)
H7	0.0634 (14)	−0.340 (2)	0.4490 (12)	0.078 (6)*
C8	0.12173 (12)	−0.2108 (2)	0.54007 (11)	0.0501 (4)
C9	0.15440 (14)	−0.0625 (2)	0.56225 (12)	0.0563 (5)
H9	0.1773 (13)	−0.045 (2)	0.6160 (13)	0.065 (6)*
C10	0.15375 (13)	0.0592 (2)	0.50585 (11)	0.0536 (5)
H10	0.1772 (13)	0.161 (2)	0.5228 (11)	0.064 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.1061 (12)	0.0596 (8)	0.0664 (9)	0.0081 (8)	−0.0178 (9)	0.0111 (7)
O2	0.1083 (13)	0.0960 (12)	0.0748 (11)	−0.0164 (10)	−0.0257 (10)	0.0297 (9)
O3	0.1163 (13)	0.0583 (9)	0.0974 (12)	−0.0137 (9)	−0.0058 (10)	0.0163 (8)
N1	0.0586 (9)	0.0459 (7)	0.0418 (8)	−0.0054 (7)	−0.0048 (7)	−0.0049 (6)
N2	0.0576 (10)	0.0686 (11)	0.0665 (11)	0.0035 (9)	0.0008 (9)	0.0131 (9)
C1	0.0868 (16)	0.0538 (12)	0.0615 (13)	−0.0091 (12)	−0.0020 (12)	0.0044 (10)
C2	0.0720 (13)	0.0498 (10)	0.0544 (11)	−0.0060 (10)	0.0003 (11)	−0.0067 (9)
C3	0.0624 (13)	0.0599 (12)	0.0477 (11)	−0.0024 (10)	−0.0086 (9)	−0.0048 (9)
C4	0.0829 (15)	0.0636 (12)	0.0478 (11)	0.0061 (12)	−0.0116 (11)	0.0029 (9)
C5	0.0428 (9)	0.0475 (8)	0.0418 (9)	−0.0013 (8)	0.0019 (7)	−0.0054 (7)
C6	0.0722 (13)	0.0569 (11)	0.0476 (11)	−0.0143 (10)	−0.0093 (10)	−0.0055 (9)
C7	0.0682 (12)	0.0497 (10)	0.0617 (12)	−0.0106 (10)	−0.0015 (10)	−0.0030 (9)
C8	0.0467 (9)	0.0521 (9)	0.0514 (10)	0.0024 (8)	0.0028 (8)	0.0037 (8)
C9	0.0626 (12)	0.0622 (11)	0.0443 (10)	−0.0015 (9)	−0.0044 (9)	−0.0042 (8)
C10	0.0656 (11)	0.0495 (9)	0.0458 (10)	−0.0081 (9)	−0.0035 (9)	−0.0069 (8)

O1—C1	1.411 (2)	C3—H3B	0.958 (19)
O1—C4	1.418 (2)	C3—C4	1.488 (3)
O2—N2	1.224 (2)	C4—H4A	0.97 (2)
O3—N2	1.227 (2)	C4—H4B	1.02 (2)
N1—C2	1.463 (2)	C5—C6	1.404 (2)
N1—C3	1.463 (2)	C5—C10	1.406 (2)
N1—C5	1.371 (2)	C6—H6	0.93 (2)
N2—C8	1.444 (2)	C6—C7	1.369 (3)
C1—H1A	1.03 (2)	C7—H7	0.96 (2)
C1—H1B	0.98 (2)	C7—C8	1.373 (3)
C1—C2	1.499 (3)	C8—C9	1.378 (2)
C2—H2A	0.99 (2)	C9—H9	0.95 (2)
C2—H2B	0.99 (2)	C9—C10	1.371 (3)
C3—H3A	1.00 (2)	C10—H10	0.957 (18)
C1—O1—C4	108.61 (15)	O1—C4—C3	111.68 (18)
C2—N1—C3	113.67 (15)	O1—C4—H4A	106.5 (11)
C5—N1—C2	120.60 (14)	O1—C4—H4B	109.0 (11)
C5—N1—C3	120.47 (14)	C3—C4—H4A	109.4 (11)
O2—N2—O3	122.50 (17)	C3—C4—H4B	108.9 (11)
O2—N2—C8	118.51 (17)	H4A—C4—H4B	111.5 (16)
O3—N2—C8	118.98 (17)	N1—C5—C6	121.23 (15)
O1—C1—H1A	108.8 (12)	N1—C5—C10	122.24 (15)
O1—C1—H1B	106.8 (11)	C6—C5—C10	116.50 (16)
O1—C1—C2	112.60 (18)	C5—C6—H6	121.2 (12)
H1A—C1—H1B	110.1 (17)	C7—C6—C5	121.78 (18)
C2—C1—H1A	108.2 (12)	C7—C6—H6	117.0 (12)
C2—C1—H1B	110.3 (12)	C6—C7—H7	121.1 (12)
N1—C2—C1	111.18 (17)	C6—C7—C8	119.81 (18)
N1—C2—H2A	110.4 (11)	C8—C7—H7	119.1 (12)
N1—C2—H2B	109.4 (11)	C7—C8—N2	119.25 (17)
C1—C2—H2A	108.0 (11)	C7—C8—C9	120.55 (17)
C1—C2—H2B	109.2 (11)	C9—C8—N2	120.20 (17)
H2A—C2—H2B	108.6 (16)	C8—C9—H9	120.3 (11)
N1—C3—H3A	109.2 (12)	C10—C9—C8	119.62 (18)
N1—C3—H3B	110.2 (11)	C10—C9—H9	120.1 (11)
N1—C3—C4	111.20 (16)	C5—C10—H10	120.4 (11)
H3A—C3—H3B	105.7 (16)	C9—C10—C5	121.68 (17)
C4—C3—H3A	111.2 (12)	C9—C10—H10	117.9 (11)
C4—C3—H3B	109.2 (11)