(E)-3-(6-Nitro­benzo[d][1,3]dioxol-5-yl)-1-(2,4,6-trimethoxy­phen­yl)prop-2-en-1-one

Loghmani-Khouzani, H.; Abdul Rahman, N.; Robinson, W.T.; Yaeghoobi, M.; Kia, R.

doi:10.1107/S1600536809036435

(E)-3-(6-Nitrobenzo[d][1,3]dioxol-5-yl)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one

H. Loghmani-Khouzani, N. Abdul Rahman, W. T. Robinson, M. Yaeghoobi and R. Kia

In the molecule of the title compound, C₁₉H₁₇NO₈, the benzodioxole unit is oriented at a dihedral angle of 61.45 (6)° with respect to the methoxy-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, intermolecular C—H

O interactions link the molecules into chains through R²₂(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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809036435/hk2765sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809036435/hk2765Isup2.hkl Contains datablock I

CCDC reference: 751284

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R factor = 0.032
wR factor = 0.083
Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      42.00 A   3 
PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) .....         10 Ang.

Alert level G
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)        100 Deg.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Aldol condensation reactions are important synthetic reactions and by classical methods they were performed in the presence of strong bases (Nielsen & Houlihan, 1968). Chalcones are open chain flavonides consisting of two aromatic rings linked by an α,β-unsaturated keton moiety. Chalcones have shown a wide variety of anticancer (Lawrence et al., 2006), anti-inflammatory (Ko et al., 2003), antimicrobial (Go et al., 2005) and antifungal (Nowakowska, 2007) activies. Crystal structures of some Chalcones were reported (Lawrence et al., 2006; Liu et al., 2002). They showed the Chalcone molecules are in s-trans conformation.

In the molecule of the title compound, (Fig. 1), a new chalcone derivative, the dihedral angle between the benzodioxole ring and the methoxy-substituted phenyl ring is 61.45 (6)°. The nitro-group is tilted with respect to the benzene ring to which it is attached by a dihedral angle of 31.86 (17)°.

In the crystal structure, intermolecular C-H···O interactions link the molecules into chains through R²₂(8) ring motifs (Bernstein et al., 1995) (Fig. 2), in which they may be effective in the stabilization of the structure. The π···π contacts between the benzodioxole rings, Cg1—Cg2ⁱ, Cg2—Cg2ⁱ and Cg2—Cg2ⁱⁱ [symmetry codes: (i) -x, 2 - y, -z, (ii) 1 - x, 2 - y, -z, where Cg1 and Cg2 are centroids of the rings (O4/O5/C7/C8/C16) and (C4-C9), respectively] may further stabilize the structure, with centroid-centroid distances of 3.7610 (9), 3.6613 (9) and 3.7975 (9) Å, respectively.

Related literature top

For general background, 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 top

The title compound was obtained according to a literature method (Lawrence et al., 2006), and crystallized in glacial acetic acid. Pale yellow, solid; m.p. 477-479 K; ¹H NMR (400 MHz; CDCl₃): δ 7.70 (d, 1H, J = 16 Hz), 7.50 (s, 1H), 7.24 (s, 1H), 6.70 (d, 1H, J = 16 Hz), 6.19 (s, 2H), 6.08 (s, 2H), 3.88 (s, 3H), 3.76 (s, 6H). ¹³C NMR (126 MHz; CDCl₃): δ 194.3 (C═O), 162.3 (C), 160.0(C), 151.9 (C), 148.0 (C), 146.0 (C), 145.0 (C), 142.9 (C), 140.6 (C), 132.6 (C), 120.0 (CH), 114.3 (C), 107.5 (CH), 105.6 (CH), 103.3 (CH), 90.5 (CH₂), 55.0 (3CH₃). IR (KBr, cm^-1 ): 3015, 1647 (C═O), 1605, 1492, 1511, 1488, 891, 823, 762, 649.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. A partial packing diagram. Hydrogen bonds are shown as dashed lines.

(E)-3-(6-Nitrobenzo[d][1,3]dioxol-5-yl)-1-(2,4,6- trimethoxyphenyl) prop-2-en-1-one top

Crystal data top

C₁₉H₁₇NO₈	Z = 2
M_r = 387.34	F(000) = 404
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0394P)² + 0.3499P] where P = (F_o² + 2F_c²)/3
3038 reflections	(Δ/σ)_max < 0.001
256 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₉H₁₇NO₈	γ = 105.384 (1)°
M_r = 387.34	V = 882.91 (2) Å³
Triclinic, P1	Z = 2
a = 7.3044 (1) Å	Mo Kα radiation
b = 10.1264 (1) Å	µ = 0.12 mm⁻¹
c = 12.8600 (2) Å	T = 296 K
α = 93.112 (1)°	0.24 × 0.14 × 0.10 mm
β = 103.959 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3038 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2733 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.989	R_int = 0.013
4805 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.04	Δρ_max = 0.21 e Å⁻³
3038 reflections	Δρ_min = −0.22 e Å⁻³
256 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇NO₈
M_r	387.34
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.3044 (1), 10.1264 (1), 12.8600 (2)
α, β, γ (°)	93.112 (1), 103.959 (1), 105.384 (1)
V (Å³)	882.91 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.24 × 0.14 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.973, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	4805, 3038, 2733
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.083, 1.04
No. of reflections	3038
No. of parameters	256
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.22

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).