2-(1-Methyl-ethoxy)-5-nitro-phenyl N-methyl-carbamate.

In the title compound, C(11)H(14)N(2)O(5), the nitro group is approximately coplanar with the benzene ring, making a dihedral angle of 4.26 (17)°. The dihedral angle between the methyl-carbamate group and the benzene ring is 72.47 (6)°. There is a strong inter-molecular N-H⋯O hydrogen bond between the N and O atoms from adjacent methyl-carbamate groups, forming a one-dimensional network along the a axis.

Related literature

For general background, see: Wang et al. (1998 ▶); Moreno et al. (2001 ▶). For related structures, see: Czugler & Kalman (1975 ▶); Xu et al. (2005 ▶). For the synthesis, see: Allan et al. (1926 ▶).

Experimental

Crystal data

C11H14N2O5

M = 254.24

Triclinic,

a = 5.034 (2) Å

b = 10.4221 (16) Å

c = 12.6319 (12) Å

α = 91.361 (3)°

β = 97.492 (2)°

γ = 94.6930 (10)°

V = 654.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 291 (2) K

0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.97, T max = 0.98

7186 measured reflections

3172 independent reflections

2005 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.105

S = 1.03

3172 reflections

167 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040622/fj2175sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040622/fj2175Isup2.hkl

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

C11H14N2O5	Z = 2
Mr = 254.24	F(000) = 268
Triclinic, P1	Dx = 1.290 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.034 (2) Å	Cell parameters from 825 reflections
b = 10.4221 (16) Å	θ = 2.1–25.4°
c = 12.6319 (12) Å	µ = 0.10 mm−1
α = 91.361 (3)°	T = 291 K
β = 97.492 (2)°	Block, colourless
γ = 94.693 (1)°	0.30 × 0.26 × 0.24 mm
V = 654.5 (3) Å3

Bruker SMART APEX CCD diffractometer	3172 independent reflections
Radiation source: sealed tube	2005 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 28.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −6→6
Tmin = 0.97, Tmax = 0.98	k = −13→13
7186 measured reflections	l = −10→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.04P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3172 reflections	Δρmax = 0.25 e Å−3
167 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (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
C1	0.6429 (3)	1.05070 (14)	0.65269 (13)	0.0418 (3)
C2	0.4552 (3)	1.04573 (14)	0.72651 (12)	0.0408 (3)
H2	0.4010	1.1205	0.7557	0.049*
C3	0.3576 (3)	0.92824 (15)	0.75300 (12)	0.0401 (3)
C4	0.4281 (3)	0.81480 (14)	0.70606 (12)	0.0404 (3)
C5	0.6183 (3)	0.82349 (14)	0.63360 (12)	0.0410 (3)
H5	0.6732	0.7492	0.6039	0.049*
C6	0.7215 (3)	0.94193 (14)	0.60731 (12)	0.0412 (3)
H6	0.8450	0.9487	0.5586	0.049*
C7	0.4126 (3)	0.58077 (15)	0.71348 (12)	0.0419 (3)
H7	0.6049	0.5905	0.7068	0.050*
C8	0.3506 (4)	0.49615 (16)	0.80518 (15)	0.0503 (4)
H8A	0.4181	0.5406	0.8719	0.075*
H8B	0.4351	0.4173	0.8004	0.075*
H8C	0.1596	0.4772	0.8011	0.075*
C9	0.2464 (4)	0.52696 (15)	0.61402 (13)	0.0475 (4)
H9A	0.0596	0.5236	0.6231	0.071*
H9B	0.2939	0.4417	0.5990	0.071*
H9C	0.2783	0.5809	0.5556	0.071*
C10	0.2341 (3)	0.86019 (14)	0.91676 (12)	0.0379 (3)
C11	0.0362 (3)	0.77353 (16)	1.06731 (13)	0.0446 (4)
H11A	0.1398	0.7002	1.0669	0.067*
H11B	−0.1414	0.7466	1.0827	0.067*
H11C	0.1217	0.8356	1.1211	0.067*
N1	0.7563 (3)	1.17674 (12)	0.62443 (11)	0.0435 (3)
N2	0.0186 (3)	0.83114 (12)	0.96365 (10)	0.0403 (3)
H2A	−0.1364	0.8468	0.9318	0.048*
O1	0.6715 (2)	1.27246 (10)	0.66209 (9)	0.0473 (3)
O2	0.9315 (2)	1.18325 (10)	0.56528 (9)	0.0446 (3)
O3	0.3060 (2)	0.70444 (10)	0.73769 (9)	0.0420 (3)
O4	0.1650 (2)	0.91925 (10)	0.82168 (9)	0.0418 (3)
O5	0.4638 (2)	0.84188 (10)	0.95050 (9)	0.0421 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0464 (9)	0.0377 (7)	0.0423 (8)	0.0040 (6)	0.0085 (7)	0.0037 (6)
C2	0.0388 (8)	0.0429 (8)	0.0423 (8)	0.0116 (6)	0.0067 (6)	0.0029 (6)
C3	0.0387 (8)	0.0459 (8)	0.0372 (8)	0.0083 (6)	0.0084 (6)	−0.0029 (6)
C4	0.0410 (8)	0.0418 (8)	0.0404 (8)	0.0090 (6)	0.0110 (6)	−0.0028 (6)
C5	0.0468 (9)	0.0389 (7)	0.0389 (8)	0.0066 (6)	0.0111 (6)	−0.0056 (6)
C6	0.0428 (8)	0.0432 (8)	0.0396 (8)	0.0111 (6)	0.0081 (6)	0.0020 (6)
C7	0.0422 (8)	0.0495 (8)	0.0368 (8)	0.0112 (7)	0.0107 (6)	0.0048 (6)
C8	0.0526 (10)	0.0487 (9)	0.0528 (10)	0.0121 (7)	0.0124 (8)	0.0120 (7)
C9	0.0516 (10)	0.0448 (9)	0.0474 (9)	0.0104 (7)	0.0098 (7)	−0.0148 (7)
C10	0.0319 (7)	0.0431 (8)	0.0404 (8)	0.0099 (6)	0.0081 (6)	−0.0047 (6)
C11	0.0439 (9)	0.0507 (9)	0.0422 (9)	0.0122 (7)	0.0101 (7)	0.0093 (7)
N1	0.0403 (7)	0.0433 (7)	0.0477 (8)	0.0027 (5)	0.0091 (6)	0.0016 (5)
N2	0.0333 (6)	0.0458 (7)	0.0453 (8)	0.0124 (5)	0.0118 (5)	0.0096 (5)
O1	0.0508 (7)	0.0413 (6)	0.0529 (7)	0.0042 (5)	0.0191 (5)	0.0017 (5)
O2	0.0530 (7)	0.0433 (6)	0.0387 (6)	−0.0037 (5)	0.0141 (5)	0.0074 (4)
O3	0.0415 (6)	0.0427 (6)	0.0437 (6)	0.0036 (4)	0.0136 (5)	−0.0016 (4)
O4	0.0447 (6)	0.0411 (5)	0.0450 (6)	0.0169 (5)	0.0170 (5)	0.0039 (4)
O5	0.0360 (6)	0.0487 (6)	0.0449 (6)	0.0140 (5)	0.0097 (5)	0.0127 (5)

C1—C6	1.368 (2)	C8—H8A	0.9600
C1—C2	1.410 (2)	C8—H8B	0.9600
C1—N1	1.4600 (19)	C8—H8C	0.9600
C2—C3	1.348 (2)	C9—H9A	0.9600
C2—H2	0.9300	C9—H9B	0.9600
C3—O4	1.3818 (18)	C9—H9C	0.9600
C3—C4	1.402 (2)	C10—O5	1.2107 (18)
C4—O3	1.3530 (19)	C10—N2	1.3195 (18)
C4—C5	1.408 (2)	C10—O4	1.3797 (19)
C5—C6	1.365 (2)	C11—N2	1.4487 (19)
C5—H5	0.9300	C11—H11A	0.9600
C6—H6	0.9300	C11—H11B	0.9600
C7—O3	1.4766 (18)	C11—H11C	0.9600
C7—C9	1.486 (2)	N1—O1	1.2263 (17)
C7—C8	1.521 (2)	N1—O2	1.2270 (17)
C7—H7	0.9800	N2—H2A	0.8600
C6—C1—C2	122.26 (14)	C7—C8—H8C	109.5
C6—C1—N1	119.34 (15)	H8A—C8—H8C	109.5
C2—C1—N1	118.40 (14)	H8B—C8—H8C	109.5
C3—C2—C1	117.29 (14)	C7—C9—H9A	109.5
C3—C2—H2	121.4	C7—C9—H9B	109.5
C1—C2—H2	121.4	H9A—C9—H9B	109.5
C2—C3—O4	119.06 (13)	C7—C9—H9C	109.5
C2—C3—C4	122.00 (15)	H9A—C9—H9C	109.5
O4—C3—C4	118.72 (13)	H9B—C9—H9C	109.5
O3—C4—C3	115.20 (14)	O5—C10—N2	126.72 (15)
O3—C4—C5	125.76 (13)	O5—C10—O4	122.87 (14)
C3—C4—C5	119.03 (14)	N2—C10—O4	110.40 (13)
C6—C5—C4	119.41 (14)	N2—C11—H11A	109.5
C6—C5—H5	120.3	N2—C11—H11B	109.5
C4—C5—H5	120.3	H11A—C11—H11B	109.5
C5—C6—C1	119.92 (15)	N2—C11—H11C	109.5
C5—C6—H6	120.0	H11A—C11—H11C	109.5
C1—C6—H6	120.0	H11B—C11—H11C	109.5
O3—C7—C9	106.04 (13)	O1—N1—O2	122.72 (13)
O3—C7—C8	104.34 (12)	O1—N1—C1	117.78 (13)
C9—C7—C8	108.30 (15)	O2—N1—C1	119.50 (13)
O3—C7—H7	112.5	C10—N2—C11	121.78 (13)
C9—C7—H7	112.5	C10—N2—H2A	119.1
C8—C7—H7	112.5	C11—N2—H2A	119.1
C7—C8—H8A	109.5	C4—O3—C7	118.97 (12)
C7—C8—H8B	109.5	C10—O4—C3	116.28 (12)
H8A—C8—H8B	109.5
C6—C1—C2—C3	1.2 (2)	C2—C1—N1—O1	−3.8 (2)
N1—C1—C2—C3	−178.66 (15)	C6—C1—N1—O2	−4.2 (2)
C1—C2—C3—O4	−177.36 (14)	C2—C1—N1—O2	175.73 (15)
C1—C2—C3—C4	−2.9 (2)	O5—C10—N2—C11	1.4 (2)
C2—C3—C4—O3	−177.54 (14)	O4—C10—N2—C11	−177.13 (13)
O4—C3—C4—O3	−3.1 (2)	C3—C4—O3—C7	−165.57 (13)
C2—C3—C4—C5	3.7 (3)	C5—C4—O3—C7	13.1 (2)
O4—C3—C4—C5	178.15 (14)	C9—C7—O3—C4	−96.64 (16)
O3—C4—C5—C6	178.71 (15)	C8—C7—O3—C4	149.11 (14)
C3—C4—C5—C6	−2.7 (2)	O5—C10—O4—C3	15.7 (2)
C4—C5—C6—C1	1.1 (3)	N2—C10—O4—C3	−165.71 (12)
C2—C1—C6—C5	−0.3 (3)	C2—C3—O4—C10	−118.54 (16)
N1—C1—C6—C5	179.56 (14)	C4—C3—O4—C10	66.83 (18)
C6—C1—N1—O1	176.26 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5i	0.86	2.05	2.788 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O5i	0.86	2.05	2.788 (2)	143

Symmetry code: (i) .