(E)-5-(2-Nitro­prop-1-en­yl)-2,3-dihydro-1-benzofuran

Xu, H.; Sun, H.; Xu, N.

doi:10.1107/S1600536809023277

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1691

doi:10.1107/S1600536809023277

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(E)-5-(2-Nitroprop-1-enyl)-2,3-dihydro-1-benzofuran

Hong Xu,^a ^* Hongshun Sun ^b and Ning Xu ^a

^aDepartment of Chemical Engineering, Nanjing College of Chemical Technology, Geguan Road No. 265 Nanjing, Nanjing 210048, People's Republic of China, and ^bDepartment of Applied Chemistry, Nanjing College of Chemical Technology, Geguan Road No. 265 Nanjing, Nanjing 210048, People's Republic of China
^*Correspondence e-mail: njutshs@126.com

(Received 6 May 2009; accepted 17 June 2009; online 27 June 2009)

The asymmetric unit of the title compound, C₁₁H₁₁NO₃, contains two crystallographically independent molecules. The aromatic rings are oriented at a dihedral angle of 56.17 (5)°. The furan rings adopt envelope conformations. Intramolecular C—H⋯N interactions results in the formation of two six-membered rings with twisted conformations. In the crystal structure, three weak C—H⋯π interactions are found.

Related literature

For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₁H₁₁NO₃
M_r = 205.21
Monoclinic, P 2₁
a = 6.1280 (12) Å
b = 15.369 (3) Å
c = 11.193 (2) Å
β = 101.38 (3)°
V = 1033.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 294 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.981, T_max = 0.990
2548 measured reflections
2335 independent reflections
1289 reflections with I > 2σ(I)
R_int = 0.031
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.163
S = 1.01
2335 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯N1	0.93	2.58	3.096 (8)	116
C18—H18A⋯N2	0.93	2.60	3.094 (7)	114
C4—H4A⋯Cg4	0.97	2.88	3.673 (8)	140
C8—H8A⋯Cg3ⁱ	0.93	2.92	3.578 (8)	129
C15—H15B⋯Cg2	0.97	2.85	3.636 (7)	139
C19—H19A⋯Cg2ⁱⁱ	0.93	2.75	3.497 (7)	139
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+1]$ . Cg2, Cg3 and Cg4 are the centroids of the C2/C3/C5–C8, O4/C12–C15 and C13/C14/C16–C19 rings, respectively.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023277/hk2683sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809023277/hk2683Isup2.hkl

checkCIF report

Comment top

Some derivatives of benzol are important chemical materials. We report herein the crystal structure of the title compound.

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1), in which the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings B (C2/C3/C5-C8) and D (C13/C14/C16-C19) are, of course, planar and the dihedral angle between them is B/D = 56.17 (5)°. Rings A (O1/C1-C4) and C (O4/C12-C15) adopt envelope conformations with atoms C1 and C12 displaced by -0.189 (4) and -0.124 (5) Å from the planes of the other rings atoms. The moieties E (N1/C9-C11) and F (N2/C20-C22) are planar [the maximum deviations are -0.002 (4) and 0.016 (4) Å for atoms C10 and C21, respectively], and they are oriented with respect to the adjacent rings at dihedral angles of B/E = 32.39 (4) and D/F = 35.26 (5) °. Intramolecular C-H···N interactions (Table 1) results in the formations of two six-membered rings (N1/C6/C7/C9/C10/H7A) and (N2/C17/C18/C20/C21/H18A) having twisted conformations.

In the crystal structure, three weak C—H···π interactions are found.

Related literature top

For bond-length data, see: Allen et al. (1987). Cg2, Cg3 and Cg4 are the centroids of the C2/C3/C5–C8, O4/C12–C15 and C13/C14/C16–C19 rings, respectively.

Experimental top

For the preparation of the title compound, ammonium acetate (0.92 g, 12 mmol) was added to a solution of 5-formyl-2,3-dihydrobenzofuran (3.3 g, 22.3 mmol) in nitroethane (10 ml). The mixture was heated with stirring to 383 K in an oil bath for 3.5 h. The volatiles were then removed by rotary evaporation. The crude product was triturated in cold CH₃OH (10 ml), collected by filtration (yield; 3.06 g, 67%). Crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (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 30% probability level.

(E)-5-(2-Nitroprop-1-enyl)-2,3-dihydro-1-benzofuran top

Crystal data top

C₁₁H₁₁NO₃	F(000) = 432
M_r = 205.21	D_x = 1.319 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 6.1280 (12) Å	θ = 10–13°
b = 15.369 (3) Å	µ = 0.10 mm⁻¹
c = 11.193 (2) Å	T = 294 K
β = 101.38 (3)°	Block, colorless
V = 1033.5 (4) Å³	0.20 × 0.10 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1289 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 27.0°, θ_min = 1.9°
ω/2θ scans	h = 0→7
Absorption correction: ψ scan (North et al., 1968)	k = 0→19
T_min = 0.981, T_max = 0.990	l = −14→14
2548 measured reflections	3 standard reflections every 120 min
2335 independent reflections	intensity decay: 1%

Refinement top

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)] = 0.055	H-atom parameters constrained
wR(F²) = 0.163	w = 1/[σ²(F_o²) + (0.08P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2335 reflections	Δρ_max = 0.16 e Å⁻³
271 parameters	Δρ_min = −0.14 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₁H₁₁NO₃	V = 1033.5 (4) Å³
M_r = 205.21	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 6.1280 (12) Å	µ = 0.10 mm⁻¹
b = 15.369 (3) Å	T = 294 K
c = 11.193 (2) Å	0.20 × 0.10 × 0.10 mm
β = 101.38 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1289 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.031
T_min = 0.981, T_max = 0.990	3 standard reflections every 120 min
2548 measured reflections	intensity decay: 1%
2335 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	271 parameters
wR(F²) = 0.163	H-atom parameters constrained
S = 1.01	Δρ_max = 0.16 e Å⁻³
2335 reflections	Δρ_min = −0.14 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.7614 (7)	0.4628 (3)	0.6830 (3)	0.0846 (13)
O2	0.2010 (8)	0.4770 (4)	0.0356 (4)	0.1031 (16)
O3	0.2751 (6)	0.3723 (3)	0.1606 (4)	0.0921 (14)
O4	0.2376 (7)	0.6709 (3)	0.6129 (4)	0.0784 (14)
O5	−0.3141 (7)	0.6604 (4)	−0.0306 (5)	0.1172 (19)
O6	−0.2291 (7)	0.7649 (3)	0.0949 (4)	0.0878 (13)
N1	0.3306 (7)	0.4276 (3)	0.0942 (5)	0.0659 (13)
N2	−0.1822 (7)	0.7083 (3)	0.0289 (4)	0.0636 (12)
C1	0.9850 (13)	0.4324 (5)	0.7308 (6)	0.098 (2)
H1A	0.9828	0.3902	0.7950	0.118*
H1B	1.0783	0.4808	0.7651	0.118*
C2	0.9084 (8)	0.4194 (3)	0.5194 (5)	0.0548 (13)
C3	0.7336 (8)	0.4598 (4)	0.5594 (5)	0.0563 (15)
C4	1.0773 (10)	0.3913 (5)	0.6293 (5)	0.0720 (16)
H4A	1.0837	0.3285	0.6369	0.086*
H4B	1.2244	0.4135	0.6265	0.086*
C5	0.9035 (8)	0.4120 (3)	0.3964 (5)	0.0540 (14)
H5A	1.0207	0.3856	0.3687	0.065*
C6	0.7209 (7)	0.4443 (3)	0.3137 (5)	0.0490 (12)
C7	0.5452 (8)	0.4844 (4)	0.3565 (5)	0.0550 (14)
H7A	0.4236	0.5060	0.3014	0.066*
C8	0.5529 (9)	0.4917 (4)	0.4809 (5)	0.0621 (14)
H8A	0.4370	0.5179	0.5101	0.074*
C9	0.7270 (8)	0.4392 (4)	0.1835 (5)	0.0627 (16)
H9A	0.8699	0.4389	0.1670	0.075*
C10	0.5669 (9)	0.4350 (4)	0.0849 (5)	0.0624 (15)
C11	0.5970 (10)	0.4375 (5)	−0.0440 (6)	0.084 (2)
H11A	0.7525	0.4424	−0.0456	0.126*
H11B	0.5188	0.4866	−0.0846	0.126*
H11C	0.5390	0.3849	−0.0847	0.126*
C12	0.4566 (12)	0.7054 (5)	0.6645 (5)	0.086 (2)
H12A	0.5519	0.6592	0.7046	0.103*
H12B	0.4449	0.7498	0.7244	0.103*
C13	0.3874 (8)	0.7151 (4)	0.4498 (5)	0.0555 (15)
C14	0.2113 (8)	0.6758 (4)	0.4893 (5)	0.0546 (13)
C15	0.5551 (9)	0.7439 (4)	0.5618 (5)	0.0687 (16)
H15A	0.7020	0.7205	0.5614	0.082*
H15B	0.5640	0.8069	0.5674	0.082*
C16	0.3809 (8)	0.7200 (4)	0.3276 (5)	0.0590 (14)
H16A	0.4996	0.7453	0.3001	0.071*
C17	0.2018 (8)	0.6882 (4)	0.2430 (5)	0.0512 (13)
C18	0.0343 (9)	0.6479 (3)	0.2890 (5)	0.0588 (14)
H18A	−0.0843	0.6241	0.2339	0.071*
C19	0.0323 (9)	0.6409 (4)	0.4116 (5)	0.0617 (16)
H19A	−0.0839	0.6141	0.4397	0.074*
C20	0.2089 (8)	0.6926 (4)	0.1136 (5)	0.0617 (14)
H20A	0.3522	0.6917	0.0978	0.074*
C21	0.0500 (8)	0.6977 (4)	0.0139 (5)	0.0609 (15)
C22	0.0741 (11)	0.6899 (6)	−0.1155 (5)	0.096 (2)
H22A	0.2286	0.6834	−0.1187	0.144*
H22B	0.0163	0.7413	−0.1593	0.144*
H22C	−0.0072	0.6400	−0.1518	0.144*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.106 (3)	0.093 (3)	0.061 (3)	0.016 (3)	0.032 (2)	0.002 (2)
O2	0.077 (3)	0.119 (4)	0.110 (4)	0.027 (3)	0.012 (3)	0.014 (3)
O3	0.070 (3)	0.107 (4)	0.104 (3)	−0.020 (3)	0.028 (2)	0.014 (3)
O4	0.090 (3)	0.088 (4)	0.057 (2)	−0.010 (3)	0.015 (2)	0.004 (2)
O5	0.064 (2)	0.164 (5)	0.117 (4)	−0.025 (3)	0.002 (3)	−0.039 (4)
O6	0.081 (3)	0.091 (3)	0.096 (3)	0.032 (3)	0.026 (2)	−0.004 (3)
N1	0.052 (3)	0.070 (3)	0.076 (3)	0.001 (3)	0.015 (2)	−0.002 (3)
N2	0.057 (3)	0.074 (3)	0.057 (3)	0.002 (3)	0.004 (2)	0.004 (3)
C1	0.109 (5)	0.110 (6)	0.073 (5)	0.025 (5)	0.010 (4)	0.006 (4)
C2	0.060 (3)	0.048 (3)	0.058 (3)	0.005 (3)	0.014 (3)	0.007 (3)
C3	0.062 (4)	0.051 (4)	0.062 (4)	−0.004 (3)	0.026 (3)	0.010 (3)
C4	0.065 (3)	0.074 (4)	0.074 (4)	0.011 (3)	0.008 (3)	0.015 (3)
C5	0.047 (3)	0.049 (3)	0.066 (4)	0.009 (3)	0.012 (3)	−0.002 (3)
C6	0.038 (2)	0.051 (3)	0.058 (3)	0.000 (2)	0.009 (2)	−0.002 (2)
C7	0.040 (3)	0.048 (3)	0.081 (4)	0.009 (2)	0.023 (3)	0.009 (3)
C8	0.064 (3)	0.056 (4)	0.073 (4)	0.013 (3)	0.031 (3)	0.002 (3)
C9	0.046 (3)	0.073 (4)	0.070 (4)	0.002 (3)	0.013 (3)	0.007 (3)
C10	0.059 (3)	0.069 (4)	0.063 (3)	0.002 (3)	0.023 (3)	0.004 (3)
C11	0.079 (4)	0.108 (6)	0.066 (4)	−0.019 (4)	0.016 (3)	0.001 (4)
C12	0.121 (6)	0.080 (5)	0.053 (4)	−0.014 (4)	0.006 (4)	−0.006 (4)
C13	0.048 (3)	0.048 (4)	0.071 (4)	0.005 (3)	0.013 (3)	−0.005 (3)
C14	0.056 (3)	0.052 (3)	0.056 (3)	0.000 (3)	0.013 (3)	0.004 (3)
C15	0.057 (3)	0.081 (4)	0.063 (4)	0.004 (3)	0.000 (3)	−0.007 (3)
C16	0.056 (3)	0.061 (4)	0.066 (3)	−0.002 (3)	0.028 (3)	0.004 (3)
C17	0.044 (3)	0.053 (3)	0.057 (3)	0.002 (3)	0.011 (2)	0.000 (3)
C18	0.064 (3)	0.051 (3)	0.061 (3)	−0.003 (3)	0.012 (3)	0.006 (3)
C19	0.058 (3)	0.057 (4)	0.070 (4)	−0.007 (3)	0.012 (3)	0.009 (3)
C20	0.043 (2)	0.079 (4)	0.065 (3)	−0.004 (3)	0.016 (2)	0.000 (3)
C21	0.052 (3)	0.066 (4)	0.068 (3)	0.004 (3)	0.021 (2)	0.002 (3)
C22	0.095 (4)	0.138 (7)	0.060 (4)	0.028 (5)	0.028 (3)	0.005 (4)

Geometric parameters (Å, º) top

N1—O2	1.197 (6)	C11—H11A	0.9600
N1—O3	1.221 (6)	C11—H11B	0.9600
N1—C10	1.476 (7)	C11—H11C	0.9600
N2—O5	1.194 (6)	C12—O4	1.452 (8)
N2—O6	1.211 (6)	C12—H12A	0.9700
N2—C21	1.475 (7)	C12—H12B	0.9700
C1—O1	1.446 (8)	C13—C16	1.363 (7)
C1—H1A	0.9700	C13—C14	1.383 (7)
C1—H1B	0.9700	C14—O4	1.363 (6)
C2—C5	1.375 (7)	C14—C19	1.368 (7)
C2—C3	1.386 (7)	C15—C12	1.521 (8)
C3—O1	1.362 (6)	C15—C13	1.521 (7)
C3—C8	1.362 (7)	C15—H15A	0.9700
C4—C1	1.505 (9)	C15—H15B	0.9700
C4—C2	1.506 (7)	C16—C17	1.389 (7)
C4—H4A	0.9700	C16—H16A	0.9300
C4—H4B	0.9700	C17—C18	1.383 (7)
C5—C6	1.395 (7)	C17—C20	1.458 (7)
C5—H5A	0.9300	C18—C19	1.379 (7)
C6—C7	1.404 (6)	C18—H18A	0.9300
C6—C9	1.468 (7)	C19—H19A	0.9300
C7—C8	1.389 (7)	C20—C21	1.331 (7)
C7—H7A	0.9300	C20—H20A	0.9300
C8—H8A	0.9300	C21—C22	1.489 (8)
C9—C10	1.325 (7)	C22—H22A	0.9600
C9—H9A	0.9300	C22—H22B	0.9600
C10—C11	1.490 (7)	C22—H22C	0.9600

C3—O1—C1	106.5 (4)	H11A—C11—H11B	109.5
C14—O4—C12	107.4 (4)	C10—C11—H11C	109.5
O2—N1—O3	122.7 (5)	H11A—C11—H11C	109.5
O2—N1—C10	117.9 (5)	H11B—C11—H11C	109.5
O3—N1—C10	119.4 (5)	O4—C12—C15	108.3 (5)
O5—N2—O6	124.5 (5)	O4—C12—H12A	110.0
O5—N2—C21	115.5 (5)	C15—C12—H12A	110.0
O6—N2—C21	120.0 (5)	O4—C12—H12B	110.0
O1—C1—C4	109.0 (5)	C15—C12—H12B	110.0
O1—C1—H1A	109.9	H12A—C12—H12B	108.4
C4—C1—H1A	109.9	C16—C13—C14	118.3 (5)
O1—C1—H1B	109.9	C16—C13—C15	133.8 (5)
C4—C1—H1B	109.9	C14—C13—C15	107.9 (5)
H1A—C1—H1B	108.3	O4—C14—C19	122.9 (5)
C5—C2—C3	119.6 (5)	O4—C14—C13	113.9 (5)
C5—C2—C4	132.0 (5)	C19—C14—C13	123.1 (5)
C3—C2—C4	108.4 (5)	C12—C15—C13	101.8 (5)
O1—C3—C8	124.4 (5)	C12—C15—H15A	111.4
O1—C3—C2	113.2 (5)	C13—C15—H15A	111.4
C8—C3—C2	122.4 (5)	C12—C15—H15B	111.4
C1—C4—C2	101.3 (5)	C13—C15—H15B	111.4
C1—C4—H4A	111.5	H15A—C15—H15B	109.3
C2—C4—H4A	111.5	C13—C16—C17	121.9 (5)
C1—C4—H4B	111.5	C13—C16—H16A	119.1
C2—C4—H4B	111.5	C17—C16—H16A	119.1
H4A—C4—H4B	109.3	C18—C17—C16	116.6 (5)
C2—C5—C6	119.4 (5)	C18—C17—C20	124.1 (5)
C2—C5—H5A	120.3	C16—C17—C20	119.1 (4)
C6—C5—H5A	120.3	C19—C18—C17	124.0 (5)
C5—C6—C7	119.9 (5)	C19—C18—H18A	118.0
C5—C6—C9	117.8 (4)	C17—C18—H18A	118.0
C7—C6—C9	122.2 (5)	C14—C19—C18	116.0 (5)
C8—C7—C6	120.1 (5)	C14—C19—H19A	122.0
C8—C7—H7A	120.0	C18—C19—H19A	122.0
C6—C7—H7A	120.0	C21—C20—C17	132.5 (5)
C3—C8—C7	118.7 (5)	C21—C20—H20A	113.8
C3—C8—H8A	120.7	C17—C20—H20A	113.8
C7—C8—H8A	120.7	C20—C21—N2	118.3 (5)
C10—C9—C6	132.0 (5)	C20—C21—C22	127.9 (5)
C10—C9—H9A	114.0	N2—C21—C22	113.7 (5)
C6—C9—H9A	114.0	C21—C22—H22A	109.5
C9—C10—N1	121.4 (5)	C21—C22—H22B	109.5
C9—C10—C11	126.3 (6)	H22A—C22—H22B	109.5
N1—C10—C11	112.4 (5)	C21—C22—H22C	109.5
C10—C11—H11A	109.5	H22A—C22—H22C	109.5
C10—C11—H11B	109.5	H22B—C22—H22C	109.5

C2—C3—O1—C1	7.9 (7)	C7—C6—C9—C10	−30.1 (10)
C4—C1—O1—C3	−12.6 (7)	C6—C7—C8—C3	0.3 (8)
C8—C3—O1—C1	−172.9 (6)	C6—C9—C10—N1	−5.0 (11)
O2—N1—C10—C9	129.9 (6)	C6—C9—C10—C11	174.6 (6)
O3—N1—C10—C9	−49.9 (8)	C15—C12—O4—C14	7.6 (7)
O2—N1—C10—C11	−49.8 (7)	C15—C13—C14—O4	−2.1 (6)
O3—N1—C10—C11	130.4 (6)	C15—C13—C14—C19	−178.9 (5)
O5—N2—C21—C20	−131.9 (6)	C16—C13—C14—O4	177.5 (5)
O5—N2—C21—C22	45.6 (8)	C16—C13—C14—C19	0.7 (8)
O6—N2—C21—C20	50.6 (8)	C14—C13—C16—C17	1.2 (8)
O6—N2—C21—C22	−132.0 (6)	C15—C13—C16—C17	−179.4 (6)
C5—C2—C3—O1	−179.7 (5)	C19—C14—O4—C12	173.4 (6)
C4—C2—C3—O1	−0.1 (7)	C13—C14—O4—C12	−3.5 (6)
C5—C2—C3—C8	1.0 (8)	O4—C14—C19—C18	−177.4 (5)
C4—C2—C3—C8	−179.3 (6)	C13—C14—C19—C18	−0.8 (8)
C3—C2—C5—C6	−0.8 (8)	C13—C15—C12—O4	−8.3 (7)
C4—C2—C5—C6	179.7 (6)	C12—C15—C13—C14	6.3 (6)
O1—C3—C8—C7	−180.0 (5)	C12—C15—C13—C16	−173.2 (6)
C2—C3—C8—C7	−0.8 (8)	C13—C16—C17—C18	−2.7 (8)
C2—C4—C1—O1	12.0 (7)	C13—C16—C17—C20	−177.7 (5)
C1—C4—C2—C5	172.3 (6)	C16—C17—C18—C19	2.6 (8)
C1—C4—C2—C3	−7.3 (7)	C20—C17—C18—C19	177.4 (5)
C2—C5—C6—C7	0.4 (8)	C18—C17—C20—C21	32.8 (10)
C2—C5—C6—C9	176.9 (5)	C16—C17—C20—C21	−152.5 (7)
C5—C6—C7—C8	−0.1 (8)	C17—C18—C19—C14	−0.9 (8)
C9—C6—C7—C8	−176.5 (5)	C17—C20—C21—N2	6.0 (10)
C5—C6—C9—C10	153.4 (7)	C17—C20—C21—C22	−171.0 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···N1	0.93	2.58	3.096 (8)	116
C18—H18A···N2	0.93	2.60	3.094 (7)	114
C4—H4A···Cg4	0.97	2.88	3.673 (8)	140
C8—H8A···Cg3ⁱ	0.93	2.92	3.578 (8)	129
C15—H15B···Cg2	0.97	2.85	3.636 (7)	139
C19—H19A···Cg2ⁱⁱ	0.93	2.75	3.497 (7)	139

Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+2, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁NO₃
M_r	205.21
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	294
a, b, c (Å)	6.1280 (12), 15.369 (3), 11.193 (2)
β (°)	101.38 (3)
V (Å³)	1033.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.981, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	2548, 2335, 1289
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.163, 1.01
No. of reflections	2335
No. of parameters	271
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.14

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···N1	0.93	2.58	3.096 (8)	116
C18—H18A···N2	0.93	2.60	3.094 (7)	114
C4—H4A···Cg4	0.97	2.88	3.673 (8)	140
C8—H8A···Cg3ⁱ	0.93	2.92	3.578 (8)	129
C15—H15B···Cg2	0.97	2.85	3.636 (7)	139
C19—H19A···Cg2ⁱⁱ	0.93	2.75	3.497 (7)	139

Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+2, y−1/2, −z+1.

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar