(E)-3-(6-Nitro-benzo[d][1,3]dioxol-5-yl)-1-(2,4,6-trimethoxy-phen-yl)prop-2-en-1-one.

In the mol-ecule of the title compound, C(19)H(17)NO(8), the benzodioxole unit is oriented at a dihedral angle of 61.45 (6)° with respect to the meth-oxy-substituted phenyl ring. The nitro group is not co-planar to the benzene ring to which it is attached, making a dihedral angle of 31.86 (17)°. In the crystal structure, inter-molecular C-H⋯O inter-actions link the mol-ecules into chains through R(2) (2)(8) ring motifs. The π⋯π contacts between the benzodioxole rings, [centroid-centroid distances = 3.7610 (9), 3.6613 (9) and 3.7975 (9) Å] may further stabilize the structure.

Related literature

For general background to synthesis, see: Nielsen & Houlihan (1968 ▶); Ko et al. (2003 ▶); Go et al. (2005 ▶); Nowakowska (2007 ▶). For related structures, see: Lawrence et al. (2006 ▶); Liu et al. (2002 ▶). For ring motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C19H17NO8

M = 387.34

Triclinic,

a = 7.3044 (1) Å

b = 10.1264 (1) Å

c = 12.8600 (2) Å

α = 93.112 (1)°

β = 103.959 (1)°

γ = 105.384 (1)°

V = 882.91 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.24 × 0.14 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.973, T max = 0.989

4805 measured reflections

3038 independent reflections

2733 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.083

S = 1.04

3038 reflections

256 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036435/hk2765sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036435/hk2765Isup2.hkl

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

C19H17NO8	Z = 2
Mr = 387.34	F(000) = 404
Triclinic, P1	Dx = 1.457 Mg m−3
Hall symbol: -P 1	Melting point: 497 K K
a = 7.3044 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1264 (1) Å	Cell parameters from 3206 reflections
c = 12.8600 (2) Å	θ = 2.5–32.5°
α = 93.112 (1)°	µ = 0.12 mm−1
β = 103.959 (1)°	T = 296 K
γ = 105.384 (1)°	Prism, pale yellow
V = 882.91 (2) Å3	0.24 × 0.14 × 0.10 mm

Bruker SMART APEXII CCD area-detector diffractometer	3038 independent reflections
Radiation source: fine-focus sealed tube	2733 reflections with I > 2σ(I)
graphite	Rint = 0.013
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→7
Tmin = 0.973, Tmax = 0.989	k = −11→12
4805 measured reflections	l = −15→15

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0394P)2 + 0.3499P] where P = (Fo2 + 2Fc2)/3
3038 reflections	(Δ/σ)max < 0.001
256 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.15752 (13)	0.44029 (9)	0.12868 (7)	0.0209 (2)
O2	0.54955 (19)	1.20445 (11)	0.27950 (9)	0.0430 (3)
O3	0.37219 (16)	1.00784 (10)	0.30427 (8)	0.0309 (3)
O4	0.11057 (18)	1.00352 (10)	−0.19561 (8)	0.0355 (3)
O5	0.21032 (16)	1.22795 (10)	−0.11005 (8)	0.0298 (3)
O6	0.58160 (13)	0.48499 (9)	0.17340 (7)	0.0198 (2)
O7	0.86143 (14)	0.63490 (10)	0.54849 (7)	0.0249 (2)
O8	0.23749 (13)	0.69600 (10)	0.35796 (7)	0.0210 (2)
N1	0.42880 (18)	1.09155 (12)	0.24520 (9)	0.0240 (3)
C1	0.25053 (18)	0.55935 (13)	0.16689 (10)	0.0163 (3)
C2	0.20715 (19)	0.67463 (13)	0.11028 (10)	0.0180 (3)
H2A	0.0969	0.6553	0.0515	0.022*
C3	0.31798 (19)	0.80537 (13)	0.13907 (10)	0.0186 (3)
H3A	0.4224	0.8247	0.2010	0.022*
C4	0.28680 (19)	0.92101 (13)	0.07998 (10)	0.0185 (3)
C5	0.34552 (19)	1.05839 (14)	0.12818 (10)	0.0191 (3)
C6	0.3278 (2)	1.17065 (14)	0.07231 (11)	0.0210 (3)
H6A	0.3692	1.2607	0.1069	0.025*
C7	0.24566 (19)	1.13955 (14)	−0.03640 (11)	0.0207 (3)
C8	0.1851 (2)	1.00527 (14)	−0.08729 (11)	0.0224 (3)
C9	0.2033 (2)	0.89551 (14)	−0.03263 (11)	0.0217 (3)
H9A	0.1616	0.8063	−0.0688	0.026*
C10	0.41339 (19)	0.58819 (13)	0.26927 (10)	0.0169 (3)
C11	0.40319 (19)	0.65461 (13)	0.36469 (10)	0.0177 (3)
C12	0.55162 (19)	0.67427 (13)	0.46034 (10)	0.0193 (3)
H12A	0.5443	0.7196	0.5234	0.023*
C13	0.71059 (19)	0.62434 (13)	0.45897 (11)	0.0195 (3)
C14	0.72776 (19)	0.55933 (13)	0.36521 (11)	0.0194 (3)
H14A	0.8367	0.5281	0.3656	0.023*
C15	0.57876 (19)	0.54221 (13)	0.27107 (10)	0.0169 (3)
C16	0.1199 (2)	1.14409 (14)	−0.21227 (11)	0.0261 (3)
H16A	0.1968	1.1736	−0.2631	0.031*
H16B	−0.0115	1.1523	−0.2414	0.031*
C17	0.7629 (2)	0.46353 (15)	0.16380 (12)	0.0242 (3)
H17A	0.7548	0.4414	0.0890	0.036*
H17B	0.7868	0.3887	0.2025	0.036*
H17C	0.8687	0.5460	0.1934	0.036*
C18	0.8713 (2)	0.72180 (16)	0.64213 (12)	0.0313 (4)
H18A	0.9939	0.7326	0.6950	0.047*
H18B	0.7640	0.6807	0.6718	0.047*
H18C	0.8627	0.8105	0.6226	0.047*
C19	0.2283 (2)	0.77177 (15)	0.45311 (11)	0.0245 (3)
H19A	0.1095	0.7994	0.4380	0.037*
H19B	0.3401	0.8522	0.4749	0.037*
H19C	0.2289	0.7144	0.5102	0.037*

	U11	U22	U33	U12	U13	U23
O1	0.0207 (5)	0.0174 (5)	0.0213 (5)	0.0041 (4)	0.0013 (4)	−0.0011 (4)
O2	0.0559 (8)	0.0233 (6)	0.0267 (6)	−0.0099 (5)	−0.0077 (5)	−0.0010 (5)
O3	0.0430 (6)	0.0253 (5)	0.0209 (5)	0.0040 (5)	0.0081 (5)	0.0036 (4)
O4	0.0602 (8)	0.0213 (5)	0.0176 (5)	0.0108 (5)	−0.0022 (5)	0.0031 (4)
O5	0.0397 (6)	0.0189 (5)	0.0248 (5)	0.0073 (4)	−0.0019 (4)	0.0049 (4)
O6	0.0191 (5)	0.0208 (5)	0.0201 (5)	0.0070 (4)	0.0056 (4)	−0.0017 (4)
O7	0.0214 (5)	0.0317 (5)	0.0189 (5)	0.0096 (4)	−0.0015 (4)	0.0012 (4)
O8	0.0195 (5)	0.0269 (5)	0.0177 (5)	0.0104 (4)	0.0037 (4)	−0.0013 (4)
N1	0.0283 (7)	0.0188 (6)	0.0209 (6)	0.0050 (5)	0.0013 (5)	0.0001 (5)
C1	0.0148 (6)	0.0180 (7)	0.0170 (6)	0.0045 (5)	0.0063 (5)	−0.0001 (5)
C2	0.0171 (7)	0.0220 (7)	0.0151 (6)	0.0077 (5)	0.0028 (5)	0.0012 (5)
C3	0.0184 (7)	0.0216 (7)	0.0160 (6)	0.0075 (5)	0.0036 (5)	0.0005 (5)
C4	0.0163 (7)	0.0189 (7)	0.0203 (7)	0.0048 (5)	0.0049 (5)	0.0021 (5)
C5	0.0165 (7)	0.0207 (7)	0.0175 (7)	0.0033 (5)	0.0023 (5)	0.0000 (5)
C6	0.0195 (7)	0.0158 (7)	0.0250 (7)	0.0037 (5)	0.0033 (6)	−0.0006 (5)
C7	0.0193 (7)	0.0184 (7)	0.0250 (7)	0.0065 (5)	0.0049 (6)	0.0055 (5)
C8	0.0245 (7)	0.0233 (7)	0.0176 (7)	0.0069 (6)	0.0025 (6)	0.0014 (5)
C9	0.0268 (7)	0.0165 (7)	0.0204 (7)	0.0059 (6)	0.0044 (6)	−0.0006 (5)
C10	0.0183 (7)	0.0137 (6)	0.0169 (6)	0.0026 (5)	0.0036 (5)	0.0027 (5)
C11	0.0170 (7)	0.0157 (6)	0.0201 (7)	0.0042 (5)	0.0047 (5)	0.0029 (5)
C12	0.0209 (7)	0.0187 (7)	0.0171 (6)	0.0042 (5)	0.0050 (5)	0.0010 (5)
C13	0.0179 (7)	0.0180 (6)	0.0191 (7)	0.0022 (5)	0.0008 (5)	0.0045 (5)
C14	0.0166 (7)	0.0177 (6)	0.0242 (7)	0.0057 (5)	0.0048 (5)	0.0042 (5)
C15	0.0193 (7)	0.0118 (6)	0.0189 (6)	0.0024 (5)	0.0060 (5)	0.0018 (5)
C16	0.0305 (8)	0.0225 (7)	0.0227 (7)	0.0070 (6)	0.0018 (6)	0.0069 (6)
C17	0.0231 (7)	0.0251 (7)	0.0281 (7)	0.0102 (6)	0.0105 (6)	0.0011 (6)
C18	0.0335 (9)	0.0357 (9)	0.0194 (7)	0.0127 (7)	−0.0045 (6)	−0.0014 (6)
C19	0.0243 (7)	0.0323 (8)	0.0191 (7)	0.0121 (6)	0.0063 (6)	−0.0010 (6)

O1—C1	1.2234 (16)	C6—H6A	0.9300
O2—N1	1.2257 (16)	C7—C8	1.3847 (19)
O3—N1	1.2257 (16)	C8—C9	1.3657 (19)
O4—C8	1.3651 (16)	C9—H9A	0.9300
O4—C16	1.4372 (17)	C10—C11	1.3946 (18)
O5—C7	1.3644 (16)	C10—C15	1.4009 (18)
O5—C16	1.4310 (17)	C11—C12	1.3941 (19)
O6—C15	1.3615 (15)	C12—C13	1.3874 (19)
O6—C17	1.4299 (16)	C12—H12A	0.9300
O7—C13	1.3649 (16)	C13—C14	1.3905 (19)
O7—C18	1.4280 (17)	C14—C15	1.3862 (19)
O8—C11	1.3677 (15)	C14—H14A	0.9300
O8—C19	1.4339 (16)	C16—H16A	0.9700
N1—C5	1.4637 (17)	C16—H16B	0.9700
C1—C2	1.4732 (18)	C17—H17A	0.9600
C1—C10	1.5007 (18)	C17—H17B	0.9600
C2—C3	1.3337 (19)	C17—H17C	0.9600
C2—H2A	0.9300	C18—H18A	0.9600
C3—C4	1.4680 (18)	C18—H18B	0.9600
C3—H3A	0.9300	C18—H18C	0.9600
C4—C5	1.4017 (19)	C19—H19A	0.9600
C4—C9	1.4092 (18)	C19—H19B	0.9600
C5—C6	1.3954 (19)	C19—H19C	0.9600
C6—C7	1.3642 (19)
C8—O4—C16	106.10 (10)	O8—C11—C10	115.53 (11)
C7—O5—C16	106.10 (10)	C12—C11—C10	121.51 (12)
C15—O6—C17	117.41 (10)	C13—C12—C11	118.22 (12)
C13—O7—C18	117.45 (11)	C13—C12—H12A	120.9
C11—O8—C19	116.76 (10)	C11—C12—H12A	120.9
O2—N1—O3	123.06 (12)	O7—C13—C12	123.09 (12)
O2—N1—C5	117.74 (11)	O7—C13—C14	114.85 (12)
O3—N1—C5	119.18 (11)	C12—C13—C14	122.06 (12)
O1—C1—C2	119.91 (12)	C15—C14—C13	118.46 (12)
O1—C1—C10	120.19 (11)	C15—C14—H14A	120.8
C2—C1—C10	119.86 (11)	C13—C14—H14A	120.8
C3—C2—C1	123.32 (12)	O6—C15—C14	124.12 (12)
C3—C2—H2A	118.3	O6—C15—C10	114.43 (11)
C1—C2—H2A	118.3	C14—C15—C10	121.42 (12)
C2—C3—C4	124.64 (12)	O5—C16—O4	107.78 (10)
C2—C3—H3A	117.7	O5—C16—H16A	110.1
C4—C3—H3A	117.7	O4—C16—H16A	110.1
C5—C4—C9	117.26 (12)	O5—C16—H16B	110.1
C5—C4—C3	123.70 (12)	O4—C16—H16B	110.1
C9—C4—C3	118.94 (12)	H16A—C16—H16B	108.5
C6—C5—C4	124.53 (12)	O6—C17—H17A	109.5
C6—C5—N1	115.44 (11)	O6—C17—H17B	109.5
C4—C5—N1	120.02 (12)	H17A—C17—H17B	109.5
C7—C6—C5	115.53 (12)	O6—C17—H17C	109.5
C7—C6—H6A	122.2	H17A—C17—H17C	109.5
C5—C6—H6A	122.2	H17B—C17—H17C	109.5
C6—C7—O5	127.98 (12)	O7—C18—H18A	109.5
C6—C7—C8	121.86 (12)	O7—C18—H18B	109.5
O5—C7—C8	110.16 (12)	H18A—C18—H18B	109.5
O4—C8—C9	127.62 (12)	O7—C18—H18C	109.5
O4—C8—C7	109.79 (12)	H18A—C18—H18C	109.5
C9—C8—C7	122.58 (12)	H18B—C18—H18C	109.5
C8—C9—C4	118.24 (12)	O8—C19—H19A	109.5
C8—C9—H9A	120.9	O8—C19—H19B	109.5
C4—C9—H9A	120.9	H19A—C19—H19B	109.5
C11—C10—C15	118.31 (12)	O8—C19—H19C	109.5
C11—C10—C1	122.38 (11)	H19A—C19—H19C	109.5
C15—C10—C1	119.26 (11)	H19B—C19—H19C	109.5
O8—C11—C12	122.95 (12)
O1—C1—C2—C3	−171.07 (12)	O1—C1—C10—C11	−114.47 (14)
C10—C1—C2—C3	6.82 (19)	C2—C1—C10—C11	67.64 (16)
C1—C2—C3—C4	175.54 (12)	O1—C1—C10—C15	62.88 (17)
C2—C3—C4—C5	153.75 (13)	C2—C1—C10—C15	−115.00 (13)
C2—C3—C4—C9	−29.9 (2)	C19—O8—C11—C12	4.76 (18)
C9—C4—C5—C6	−0.4 (2)	C19—O8—C11—C10	−176.43 (11)
C3—C4—C5—C6	176.01 (12)	C15—C10—C11—O8	−179.48 (11)
C9—C4—C5—N1	178.47 (12)	C1—C10—C11—O8	−2.09 (18)
C3—C4—C5—N1	−5.2 (2)	C15—C10—C11—C12	−0.65 (19)
O2—N1—C5—C6	−31.32 (18)	C1—C10—C11—C12	176.73 (12)
O3—N1—C5—C6	146.93 (13)	O8—C11—C12—C13	177.98 (11)
O2—N1—C5—C4	149.75 (14)	C10—C11—C12—C13	−0.76 (19)
O3—N1—C5—C4	−32.00 (19)	C18—O7—C13—C12	−11.05 (19)
C4—C5—C6—C7	0.4 (2)	C18—O7—C13—C14	168.92 (12)
N1—C5—C6—C7	−178.43 (11)	C11—C12—C13—O7	−178.33 (12)
C5—C6—C7—O5	179.77 (13)	C11—C12—C13—C14	1.7 (2)
C5—C6—C7—C8	−0.2 (2)	O7—C13—C14—C15	178.85 (11)
C16—O5—C7—C6	−179.08 (14)	C12—C13—C14—C15	−1.19 (19)
C16—O5—C7—C8	0.93 (15)	C17—O6—C15—C14	−11.24 (17)
C16—O4—C8—C9	178.84 (14)	C17—O6—C15—C10	166.67 (11)
C16—O4—C8—C7	−1.85 (16)	C13—C14—C15—O6	177.46 (11)
C6—C7—C8—O4	−179.39 (13)	C13—C14—C15—C10	−0.30 (19)
O5—C7—C8—O4	0.60 (17)	C11—C10—C15—O6	−176.77 (10)
C6—C7—C8—C9	0.0 (2)	C1—C10—C15—O6	5.76 (17)
O5—C7—C8—C9	179.95 (13)	C11—C10—C15—C14	1.19 (19)
O4—C8—C9—C4	179.36 (13)	C1—C10—C15—C14	−176.27 (11)
C7—C8—C9—C4	0.1 (2)	C7—O5—C16—O4	−2.04 (15)
C5—C4—C9—C8	0.05 (19)	C8—O4—C16—O5	2.40 (16)
C3—C4—C9—C8	−176.50 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1i	0.93	2.55	3.4512 (16)	164
C6—H6A···O6ii	0.93	2.36	3.2429 (16)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1i	0.93	2.55	3.4512 (16)	164
C6—H6A⋯O6ii	0.93	2.36	3.2429 (16)	158

Symmetry codes: (i) ; (ii) .