tert-Butyl 2-methyl-2-(4-nitro-benzo-yl)propanoate.

The title compound, C(15)H(19)NO(5), is bent with a dihedral angle of 61.8 (2)° between the mean planes of the benzene ring and a group encompassing the ester functionality (O=C-O-C). The dihedral angle of 0.8 (2)° between the mean planes of the nitro group and the benzene ring indicates near coplanarity. In the crystal, each mol-ecule is linked to four adjacent mol-ecules by weak C-H⋯O hydrogen-bonding inter-actions. Both benzene H atoms ortho to the ketone O atom form C-H⋯O hydrogen bonds with the keto O atoms of two neighboring mol-ecules (of the keto and ester groups, respectively), and the two other inter-actions involve the H atoms from a methyl group of the dimethyl residue, displaying C-H⋯O inter-actions with the O atoms of the nitro groups. These four inter-actions for each mol-ecule lead to the formation of two-dimensional sheets with a hydro-philic inter-ior, held together by weak hydrogen-bonded inter-actions, and a hydro-phobic exterior composed of protruding methyl groups which interst-ack with the methyl groups in adjacent sheets.

Related literature

For the synthesis, spectroscopic characterization and reactivity of the title compound, see: Logue (1974 ▶); Logue et al. (1975 ▶). For related structures, see: Crosse et al. (2010 ▶); Gould et al. (2010 ▶); Logue et al. (2010 ▶). For the syntheses and characterization of structurally similar indanone-derived β-keto ester derivatives, see: Alemán et al. (2007 ▶); Elsner et al. (2008 ▶); Mouri et al. (2009 ▶); Noritake et al. (2008 ▶); Rigby & Dixon (2008 ▶); Wang et al. (2006 ▶). For weak hydrogen-bonded inter­actions, see: Karle et al. (2009 ▶).

Experimental

Crystal data

C15H19NO5

M = 293.31

Monoclinic,

a = 11.379 (4) Å

b = 11.393 (4) Å

c = 12.283 (5) Å

β = 94.88 (3)°

V = 1586.6 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 291 K

0.50 × 0.20 × 0.05 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.931, T max = 0.993

2933 measured reflections

2785 independent reflections

1196 reflections with I > 2σ(I)

R int = 0.072

3 standard reflections every 166 min intensity decay: 3%

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.171

S = 0.98

2785 reflections

195 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003119/zl2264sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003119/zl2264Isup2.hkl

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

C15H19NO5	F(000) = 624
Mr = 293.31	Dx = 1.228 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.379 (4) Å	θ = 10–15°
b = 11.393 (4) Å	µ = 0.09 mm−1
c = 12.283 (5) Å	T = 291 K
β = 94.88 (3)°	Prism, colourless
V = 1586.6 (10) Å3	0.50 × 0.20 × 0.05 mm
Z = 4

Enraf–Nonius TurboCAD-4 diffractometer	1196 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590	Rint = 0.072
graphite	θmax = 25.0°, θmin = 1.8°
non–profiled ω/2τ scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = 0→13
Tmin = 0.931, Tmax = 0.993	l = −14→14
2933 measured reflections	3 standard reflections every 166 min
2785 independent reflections	intensity decay: 3%

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0756P)2] where P = (Fo2 + 2Fc2)/3
2785 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Experimental. (North et al., 1968) Number of psi-scan sets used was 2. Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
N1	0.1227 (3)	0.3124 (4)	0.1368 (4)	0.0837 (12)
O1	0.1312 (4)	0.2370 (3)	0.0679 (4)	0.1350 (15)
O2	0.1050 (3)	0.2912 (3)	0.2318 (3)	0.1021 (11)
C1	0.1353 (3)	0.4356 (3)	0.1031 (3)	0.0577 (10)
C2	0.1269 (3)	0.5237 (4)	0.1783 (3)	0.0604 (11)
H2	0.1122	0.5059	0.2498	0.073*
C3	0.1404 (3)	0.6375 (4)	0.1472 (3)	0.0564 (10)
H3	0.1357	0.6976	0.198	0.068*
C4	0.1613 (3)	0.6645 (3)	0.0391 (3)	0.0502 (9)
C5	0.1682 (3)	0.5738 (4)	−0.0348 (3)	0.0624 (11)
H5	0.181	0.5911	−0.1068	0.075*
C6	0.1564 (3)	0.4586 (4)	−0.0042 (3)	0.0679 (12)
H6	0.1625	0.3979	−0.054	0.082*
C7	0.1776 (3)	0.7879 (4)	−0.0005 (3)	0.0570 (10)
O3	0.1533 (3)	0.8083 (3)	−0.0971 (2)	0.0886 (10)
C8	0.2210 (3)	0.8869 (3)	0.0759 (3)	0.0506 (9)
C9	0.2737 (4)	0.9859 (3)	0.0097 (3)	0.0721 (12)
H9A	0.3002	1.0485	0.058	0.108*
H9B	0.2145	1.015	−0.044	0.108*
H9C	0.3391	0.9559	−0.0262	0.108*
C10	0.1165 (3)	0.9360 (4)	0.1339 (3)	0.0759 (13)
H10A	0.142	1.003	0.1769	0.114*
H10B	0.088	0.8766	0.1806	0.114*
H10C	0.0543	0.9587	0.0803	0.114*
C11	0.3195 (3)	0.8458 (3)	0.1591 (3)	0.0480 (9)
O4	0.3323 (2)	0.8769 (2)	0.2523 (2)	0.0727 (8)
O5	0.3918 (2)	0.7753 (2)	0.11076 (18)	0.0583 (7)
C12	0.4942 (3)	0.7164 (4)	0.1705 (4)	0.0714 (12)
C13	0.5390 (6)	0.6385 (6)	0.0848 (5)	0.165 (3)
H13A	0.4792	0.5827	0.0607	0.248*
H13B	0.6081	0.5976	0.1148	0.248*
H13C	0.5586	0.6854	0.0239	0.248*
C14	0.4540 (5)	0.6455 (4)	0.2639 (5)	0.123 (2)
H14A	0.3995	0.5862	0.2359	0.184*
H14B	0.4158	0.6961	0.3124	0.184*
H14C	0.5209	0.6088	0.3028	0.184*
C15	0.5827 (4)	0.8075 (5)	0.2131 (5)	0.134 (2)
H15A	0.6016	0.8576	0.1542	0.2*
H15B	0.6531	0.7692	0.2438	0.2*
H15C	0.5498	0.8536	0.2684	0.2*

	U11	U22	U33	U12	U13	U23
N1	0.061 (2)	0.069 (3)	0.124 (4)	0.001 (2)	0.023 (2)	−0.001 (3)
O1	0.176 (4)	0.063 (2)	0.174 (4)	0.011 (2)	0.062 (3)	−0.010 (2)
O2	0.102 (3)	0.086 (2)	0.121 (3)	−0.008 (2)	0.025 (2)	0.028 (2)
C1	0.043 (2)	0.050 (3)	0.080 (3)	−0.005 (2)	0.005 (2)	0.003 (2)
C2	0.064 (3)	0.069 (3)	0.049 (2)	−0.013 (2)	0.0057 (19)	−0.002 (2)
C3	0.066 (3)	0.065 (3)	0.039 (2)	−0.011 (2)	0.0061 (18)	−0.0035 (19)
C4	0.046 (2)	0.069 (3)	0.0356 (19)	−0.0047 (19)	0.0026 (16)	−0.003 (2)
C5	0.063 (3)	0.081 (3)	0.044 (2)	0.000 (2)	0.0116 (19)	−0.006 (2)
C6	0.058 (3)	0.076 (3)	0.071 (3)	0.004 (2)	0.015 (2)	−0.018 (2)
C7	0.061 (2)	0.070 (3)	0.041 (2)	0.003 (2)	0.0055 (18)	0.007 (2)
O3	0.127 (3)	0.096 (2)	0.0395 (16)	−0.0103 (19)	−0.0110 (16)	0.0177 (15)
C8	0.057 (2)	0.052 (2)	0.0442 (19)	0.0064 (19)	0.0082 (18)	0.0069 (18)
C9	0.091 (3)	0.058 (3)	0.068 (3)	0.003 (2)	0.009 (2)	0.017 (2)
C10	0.068 (3)	0.089 (3)	0.071 (3)	0.029 (3)	0.012 (2)	0.007 (2)
C11	0.050 (2)	0.047 (2)	0.047 (2)	−0.0044 (19)	0.0103 (19)	−0.0005 (19)
O4	0.0762 (19)	0.093 (2)	0.0472 (16)	0.0111 (16)	−0.0022 (13)	−0.0140 (15)
O5	0.0554 (16)	0.0646 (16)	0.0550 (15)	0.0147 (14)	0.0055 (13)	−0.0037 (13)
C12	0.050 (2)	0.069 (3)	0.094 (3)	0.012 (2)	−0.002 (2)	0.004 (3)
C13	0.148 (6)	0.181 (6)	0.164 (6)	0.102 (5)	−0.002 (5)	−0.049 (5)
C14	0.096 (4)	0.098 (4)	0.172 (5)	0.012 (3)	0.000 (4)	0.071 (4)
C15	0.059 (3)	0.127 (5)	0.210 (6)	−0.021 (3)	−0.021 (4)	0.015 (5)

N1—O1	1.216 (5)	C9—H9B	0.96
N1—O2	1.225 (4)	C9—H9C	0.96
N1—C1	1.474 (5)	C10—H10A	0.96
C1—C2	1.373 (5)	C10—H10B	0.96
C1—C6	1.384 (5)	C10—H10C	0.96
C2—C3	1.365 (5)	C11—O4	1.195 (4)
C2—H2	0.93	C11—O5	1.326 (4)
C3—C4	1.403 (4)	O5—C12	1.483 (4)
C3—H3	0.93	C12—C13	1.499 (6)
C4—C5	1.381 (5)	C12—C14	1.506 (6)
C4—C7	1.505 (5)	C12—C15	1.509 (6)
C5—C6	1.375 (5)	C13—H13A	0.96
C5—H5	0.93	C13—H13B	0.96
C6—H6	0.93	C13—H13C	0.96
C7—O3	1.218 (4)	C14—H14A	0.96
C7—C8	1.523 (5)	C14—H14B	0.96
C8—C11	1.525 (5)	C14—H14C	0.96
C8—C9	1.541 (5)	C15—H15A	0.96
C8—C10	1.543 (5)	C15—H15B	0.96
C9—H9A	0.96	C15—H15C	0.96
O1—N1—O2	123.6 (4)	H9B—C9—H9C	109.5
O1—N1—C1	117.5 (4)	C8—C10—H10A	109.5
O2—N1—C1	118.9 (4)	C8—C10—H10B	109.5
C2—C1—C6	122.0 (4)	H10A—C10—H10B	109.5
C2—C1—N1	119.5 (4)	C8—C10—H10C	109.5
C6—C1—N1	118.5 (4)	H10A—C10—H10C	109.5
C3—C2—C1	119.4 (4)	H10B—C10—H10C	109.5
C3—C2—H2	120.3	O4—C11—O5	125.4 (3)
C1—C2—H2	120.3	O4—C11—C8	125.0 (3)
C2—C3—C4	120.3 (4)	O5—C11—C8	109.5 (3)
C2—C3—H3	119.8	C11—O5—C12	122.9 (3)
C4—C3—H3	119.8	O5—C12—C13	102.7 (3)
C5—C4—C3	118.8 (4)	O5—C12—C14	110.0 (3)
C5—C4—C7	118.1 (3)	C13—C12—C14	111.2 (4)
C3—C4—C7	123.1 (3)	O5—C12—C15	109.5 (3)
C6—C5—C4	121.5 (4)	C13—C12—C15	113.2 (5)
C6—C5—H5	119.3	C14—C12—C15	110.0 (4)
C4—C5—H5	119.3	C12—C13—H13A	109.5
C5—C6—C1	118.0 (4)	C12—C13—H13B	109.5
C5—C6—H6	121	H13A—C13—H13B	109.5
C1—C6—H6	121	C12—C13—H13C	109.5
O3—C7—C4	118.0 (3)	H13A—C13—H13C	109.5
O3—C7—C8	119.6 (3)	H13B—C13—H13C	109.5
C4—C7—C8	122.4 (3)	C12—C14—H14A	109.5
C7—C8—C11	111.5 (3)	C12—C14—H14B	109.5
C7—C8—C9	109.7 (3)	H14A—C14—H14B	109.5
C11—C8—C9	106.4 (3)	C12—C14—H14C	109.5
C7—C8—C10	109.3 (3)	H14A—C14—H14C	109.5
C11—C8—C10	110.7 (3)	H14B—C14—H14C	109.5
C9—C8—C10	109.2 (3)	C12—C15—H15A	109.5
C8—C9—H9A	109.5	C12—C15—H15B	109.5
C8—C9—H9B	109.5	H15A—C15—H15B	109.5
H9A—C9—H9B	109.5	C12—C15—H15C	109.5
C8—C9—H9C	109.5	H15A—C15—H15C	109.5
H9A—C9—H9C	109.5	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3i	0.93	2.51	3.191 (4)	130
C5—H5···O4ii	0.93	2.57	3.387 (5)	147
C10—H10B···O2iii	0.96	2.71	3.535 (5)	145

Torsion	X=Hb	X=CH3c	X=Cld	X=NO2e
2—1—7—8	-160.6 (2)	170.4 (2)	-175.6 (3)	-154.6 (3)
1—7—8—11	43.8 (3)	57.8 (3)	52.8 (3)	40.6 (4)
7—8—11—O3	45.9 (2)	34.1 (3)	41.4 (3)	40.6 (4)
8—11—O3—12	179.50 (17)	176.60 (19)	179.5 (2)	177.4 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3i	0.93	2.51	3.191 (4)	130
C5—H5⋯O4ii	0.93	2.57	3.387 (5)	147
C10—H10B⋯O2iii	0.96	2.71	3.535 (5)	145

Symmetry codes: (i) ; (ii) ; (iii) .