tert-Butyl 2-(4-nitro-phen-oxy)acetate.

In the title mol-ecule, C(12)H(15)NO(5), the nitro-phen-oxy portion is approximately planar (r.m.s. deviation = 0.034 Å) and makes an angle of 84.8 (1)° with respect to the -CH(2)-C(=O)-O-C fragment. In the crystal, π-π stacking is observed between nearly parallel benzene rings of adjacent mol-ecules, the centroid-centroid distance being 3.6806 (10) Å. Weak inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For a study of the biopotency of the title compound, see: Arfan et al. (2010 ▶). For related structures, see: Ali et al. (2010 ▶); Mustafa et al. (2009 ▶).

Experimental

Crystal data

C12H15NO5

M = 253.25

Monoclinic,

a = 19.2761 (7) Å

b = 12.1131 (4) Å

c = 11.7267 (5) Å

β = 111.682 (4)°

V = 2544.38 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.30 × 0.20 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.664, T max = 1.000

5580 measured reflections

2824 independent reflections

2075 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.120

S = 1.06

2824 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003229/xu5151sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003229/xu5151Isup2.hkl

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

C12H15NO5	F(000) = 1072
Mr = 253.25	Dx = 1.322 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1942 reflections
a = 19.2761 (7) Å	θ = 2.3–28.5°
b = 12.1131 (4) Å	µ = 0.10 mm−1
c = 11.7267 (5) Å	T = 100 K
β = 111.682 (4)°	Plate, colorless
V = 2544.38 (17) Å3	0.30 × 0.20 × 0.05 mm
Z = 8

Agilent SuperNova Dual diffractometer with an Atlas detector	2824 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2075 reflections with I > 2σ(I)
Mirror	Rint = 0.029
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.3°
ω scans	h = −17→24
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −13→15
Tmin = 0.664, Tmax = 1.000	l = −14→14
5580 measured reflections

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0444P)2 + 0.6948P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2824 reflections	Δρmax = 0.27 e Å−3
164 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0033 (4)

	x	y	z	Uiso*/Ueq
O1	0.37259 (7)	0.48179 (13)	0.04938 (14)	0.0505 (4)
O2	0.41306 (9)	0.58588 (13)	0.21067 (16)	0.0581 (5)
O3	0.44798 (6)	0.11669 (9)	0.44903 (11)	0.0251 (3)
O4	0.59965 (6)	0.13203 (9)	0.53127 (11)	0.0279 (3)
O5	0.60685 (5)	0.11686 (9)	0.72849 (10)	0.0233 (3)
N1	0.39810 (8)	0.49483 (14)	0.16138 (17)	0.0387 (4)
C1	0.41151 (9)	0.39685 (14)	0.23939 (17)	0.0275 (4)
C2	0.43579 (9)	0.41028 (15)	0.36502 (17)	0.0287 (4)
H2	0.4428	0.4821	0.4001	0.034*
C3	0.44980 (8)	0.31747 (14)	0.43918 (16)	0.0258 (4)
H3	0.4666	0.3249	0.5258	0.031*
C4	0.43901 (8)	0.21342 (13)	0.38562 (15)	0.0221 (4)
C5	0.41454 (8)	0.20196 (14)	0.25872 (15)	0.0240 (4)
H5	0.4076	0.1304	0.2231	0.029*
C6	0.40040 (8)	0.29378 (15)	0.18461 (16)	0.0275 (4)
H6	0.3834	0.2866	0.0979	0.033*
C7	0.48824 (8)	0.11660 (14)	0.57817 (15)	0.0250 (4)
H7A	0.4768	0.0482	0.6141	0.030*
H7B	0.4723	0.1803	0.6155	0.030*
C8	0.57178 (8)	0.12344 (13)	0.60739 (16)	0.0223 (4)
C9	0.69011 (8)	0.12075 (13)	0.78688 (16)	0.0241 (4)
C10	0.72379 (9)	0.02283 (15)	0.74544 (17)	0.0312 (4)
H10A	0.7142	0.0297	0.6576	0.047*
H10B	0.7012	−0.0455	0.7602	0.047*
H10C	0.7778	0.0210	0.7917	0.047*
C11	0.70230 (9)	0.11251 (16)	0.92190 (16)	0.0352 (5)
H11A	0.6833	0.0415	0.9379	0.053*
H11B	0.6757	0.1727	0.9440	0.053*
H11C	0.7558	0.1180	0.9711	0.053*
C12	0.71824 (9)	0.23046 (15)	0.75805 (18)	0.0341 (5)
H12A	0.7088	0.2344	0.6701	0.051*
H12B	0.7720	0.2367	0.8049	0.051*
H12C	0.6921	0.2910	0.7806	0.051*

	U11	U22	U33	U12	U13	U23
O1	0.0487 (8)	0.0646 (11)	0.0413 (10)	0.0150 (7)	0.0201 (7)	0.0271 (8)
O2	0.0813 (11)	0.0317 (9)	0.0778 (13)	0.0110 (7)	0.0485 (10)	0.0148 (9)
O3	0.0243 (6)	0.0262 (7)	0.0213 (6)	−0.0002 (4)	0.0044 (5)	0.0025 (5)
O4	0.0270 (6)	0.0348 (7)	0.0239 (7)	−0.0001 (5)	0.0118 (5)	0.0043 (6)
O5	0.0185 (6)	0.0303 (7)	0.0201 (6)	−0.0014 (4)	0.0059 (5)	0.0008 (5)
N1	0.0367 (9)	0.0391 (10)	0.0513 (12)	0.0145 (7)	0.0290 (8)	0.0197 (9)
C1	0.0242 (8)	0.0314 (10)	0.0315 (10)	0.0087 (7)	0.0159 (7)	0.0098 (8)
C2	0.0289 (9)	0.0263 (9)	0.0348 (11)	0.0030 (7)	0.0162 (8)	−0.0010 (8)
C3	0.0269 (8)	0.0295 (10)	0.0220 (9)	0.0017 (7)	0.0100 (7)	−0.0013 (8)
C4	0.0165 (7)	0.0269 (9)	0.0233 (9)	0.0020 (6)	0.0078 (6)	0.0037 (7)
C5	0.0196 (8)	0.0305 (9)	0.0221 (9)	0.0020 (6)	0.0079 (6)	−0.0023 (7)
C6	0.0189 (8)	0.0424 (11)	0.0226 (9)	0.0052 (7)	0.0093 (7)	0.0036 (8)
C7	0.0224 (8)	0.0321 (10)	0.0188 (9)	−0.0002 (6)	0.0057 (7)	0.0043 (8)
C8	0.0237 (8)	0.0203 (8)	0.0223 (9)	−0.0002 (6)	0.0078 (7)	0.0019 (7)
C9	0.0171 (8)	0.0275 (9)	0.0247 (9)	−0.0023 (6)	0.0043 (7)	−0.0019 (7)
C10	0.0232 (8)	0.0327 (10)	0.0357 (11)	0.0011 (7)	0.0086 (7)	−0.0032 (9)
C11	0.0242 (9)	0.0523 (13)	0.0250 (10)	−0.0014 (8)	0.0044 (7)	−0.0021 (9)
C12	0.0261 (9)	0.0323 (10)	0.0422 (12)	−0.0054 (7)	0.0105 (8)	−0.0013 (9)

O1—N1	1.231 (2)	C6—H6	0.9500
O2—N1	1.229 (2)	C7—C8	1.520 (2)
O3—C4	1.3641 (19)	C7—H7A	0.9900
O3—C7	1.424 (2)	C7—H7B	0.9900
O4—C8	1.2044 (19)	C9—C10	1.516 (2)
O5—C8	1.3307 (19)	C9—C11	1.516 (2)
O5—C9	1.4949 (18)	C9—C12	1.520 (2)
N1—C1	1.462 (2)	C10—H10A	0.9800
C1—C2	1.381 (3)	C10—H10B	0.9800
C1—C6	1.384 (2)	C10—H10C	0.9800
C2—C3	1.386 (2)	C11—H11A	0.9800
C2—H2	0.9500	C11—H11B	0.9800
C3—C4	1.389 (2)	C11—H11C	0.9800
C3—H3	0.9500	C12—H12A	0.9800
C4—C5	1.392 (2)	C12—H12B	0.9800
C5—C6	1.375 (2)	C12—H12C	0.9800
C5—H5	0.9500
C4—O3—C7	119.34 (12)	H7A—C7—H7B	108.1
C8—O5—C9	121.54 (12)	O4—C8—O5	127.32 (14)
O2—N1—O1	123.29 (17)	O4—C8—C7	124.28 (15)
O2—N1—C1	118.53 (18)	O5—C8—C7	108.39 (14)
O1—N1—C1	118.17 (18)	O5—C9—C10	110.06 (12)
C2—C1—C6	122.33 (16)	O5—C9—C11	101.67 (12)
C2—C1—N1	118.94 (17)	C10—C9—C11	111.34 (15)
C6—C1—N1	118.72 (17)	O5—C9—C12	109.67 (13)
C1—C2—C3	119.00 (17)	C10—C9—C12	112.49 (14)
C1—C2—H2	120.5	C11—C9—C12	111.08 (15)
C3—C2—H2	120.5	C9—C10—H10A	109.5
C2—C3—C4	119.37 (16)	C9—C10—H10B	109.5
C2—C3—H3	120.3	H10A—C10—H10B	109.5
C4—C3—H3	120.3	C9—C10—H10C	109.5
O3—C4—C3	124.42 (15)	H10A—C10—H10C	109.5
O3—C4—C5	114.94 (14)	H10B—C10—H10C	109.5
C3—C4—C5	120.59 (15)	C9—C11—H11A	109.5
C6—C5—C4	120.30 (16)	C9—C11—H11B	109.5
C6—C5—H5	119.8	H11A—C11—H11B	109.5
C4—C5—H5	119.8	C9—C11—H11C	109.5
C5—C6—C1	118.40 (16)	H11A—C11—H11C	109.5
C5—C6—H6	120.8	H11B—C11—H11C	109.5
C1—C6—H6	120.8	C9—C12—H12A	109.5
O3—C7—C8	110.82 (14)	C9—C12—H12B	109.5
O3—C7—H7A	109.5	H12A—C12—H12B	109.5
C8—C7—H7A	109.5	C9—C12—H12C	109.5
O3—C7—H7B	109.5	H12A—C12—H12C	109.5
C8—C7—H7B	109.5	H12B—C12—H12C	109.5
O2—N1—C1—C2	4.2 (2)	C3—C4—C5—C6	−0.3 (2)
O1—N1—C1—C2	−176.09 (15)	C4—C5—C6—C1	0.4 (2)
O2—N1—C1—C6	−174.92 (15)	C2—C1—C6—C5	−0.3 (2)
O1—N1—C1—C6	4.8 (2)	N1—C1—C6—C5	178.73 (13)
C6—C1—C2—C3	0.2 (2)	C4—O3—C7—C8	−76.68 (17)
N1—C1—C2—C3	−178.85 (13)	C9—O5—C8—O4	0.6 (2)
C1—C2—C3—C4	−0.1 (2)	C9—O5—C8—C7	179.79 (12)
C7—O3—C4—C3	−16.7 (2)	O3—C7—C8—O4	2.6 (2)
C7—O3—C4—C5	165.91 (13)	O3—C7—C8—O5	−176.57 (12)
C2—C3—C4—O3	−177.12 (14)	C8—O5—C9—C10	−62.81 (18)
C2—C3—C4—C5	0.1 (2)	C8—O5—C9—C11	179.09 (14)
O3—C4—C5—C6	177.24 (12)	C8—O5—C9—C12	61.45 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O4i	0.95	2.50	3.201 (2)	130
C12—H12C···O2ii	0.98	2.55	3.489 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O4i	0.95	2.50	3.201 (2)	130
C12—H12C⋯O2ii	0.98	2.55	3.489 (3)	161

Symmetry codes: (i) ; (ii) .