2-(3,4-Dimethoxy­phen­yl)-3-hydroxy­but-2-enenitrile

Shang, Z.-H.; Yu, H.-J.

doi:10.1107/S1600536807029455

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2-(3,4-Dimethoxyphenyl)-3-hydroxybut-2-enenitrile

Z.-H. Shang and H.-J. Yu

The title compound, C₁₂H₁₃NO₃, adopts its enol tautomeric form and crystallizes with two molecules in the asymmetric unit, with similar conformations. In the crystal structure, molecules interact via O—H

N hydrogen bonds, leading to infinite chains.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029455/hb2405sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029455/hb2405Isup2.hkl Contains datablock I

CCDC reference: 655604

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.002 Å
R factor = 0.046
wR factor = 0.147
Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C15    -   C16     ..       5.38 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.40
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.63
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C3     -   C4     ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C15    -   C16    ...       1.43 Ang.

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

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

Comment top

5-Aminopyrazoles posses many biological properties such as antibacterial (Kumar et al., 2005) and herbicidal activities (Jung et al., (2002). They can be prepared from substituted acetonitriles reacting with substituted hydrazines.

The title compound, (I), (Fig. 1) was obtained as part of our studies in this area and the X-ray analysis reveals that (I) is a enol with a conjugated system. There are two molecules in the asymmetric unit and intermolecular O—H···N hydrogen bonds (Table 1) help to stablize the crystal packing.

Related literature top

For background literature, see: Jung et al. (2002); Kumar et al. (2005).

Experimental top

A mixture of 2-(3,4-dimethoxyphenyl)acetonitrile (1.77 g, 10 mmol), 3,4,5-trimethoxybenzaldehyde (0.88 g, 10 mmol), and NaOEt (0.68 g, 10 mmol) in ethanol (5 ml) was stirred at room temperature and monitored by TLC. After completion of the reaction, 2 ml water was added and evaporated in vacuo. the product was purified through flash column chromatography and 50 mg of the title compound was dissolved in 100 ml absolute methanol and crystals suitable for X-ray analysis were grown by slow evaporation over a period of 15 d.

Structure description top

For background literature, see: Jung et al. (2002); Kumar et al. (2005).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids (arbitrary spheres for the H atoms).
	Fig. 2. The reaction scheme for the formation of (I).

2-(3,4-Dimethoxyphenyl)-3-hydroxybut-2-enenitrile top

Crystal data top

C₁₂H₁₃NO₃	Z = 4
M_r = 219.23	F(000) = 464
Triclinic, P1	D_x = 1.321 Mg m⁻³
Hall symbol: -P 1	Melting point = 478–480 K
a = 8.5316 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.1801 (17) Å	Cell parameters from 2572 reflections
c = 11.8021 (18) Å	θ = 2.4–26.2°
α = 82.777 (3)°	µ = 0.10 mm⁻¹
β = 81.232 (2)°	T = 294 K
γ = 85.712 (3)°	Prism, orange
V = 1102.0 (3) Å³	0.26 × 0.24 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4428 independent reflections
Radiation source: fine-focus sealed tube	3078 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
φ and ω scans	θ_max = 26.4°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −10→10
T_min = 0.976, T_max = 0.981	k = −13→9
6372 measured reflections	l = −14→14

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.046	w = 1/[σ²(F_o²) + (0.0789P)² + 0.2254P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.147	(Δ/σ)_max = 0.003
S = 1.03	Δρ_max = 0.43 e Å⁻³
4428 reflections	Δρ_min = −0.39 e Å⁻³
297 parameters	Extinction correction: SHELXL97
0 restraints	Extinction coefficient: 0.019 (3)

Crystal data top

C₁₂H₁₃NO₃	γ = 85.712 (3)°
M_r = 219.23	V = 1102.0 (3) Å³
Triclinic, P1	Z = 4
a = 8.5316 (13) Å	Mo Kα radiation
b = 11.1801 (17) Å	µ = 0.10 mm⁻¹
c = 11.8021 (18) Å	T = 294 K
α = 82.777 (3)°	0.26 × 0.24 × 0.20 mm
β = 81.232 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4428 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	3078 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.981	R_int = 0.017
6372 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.43 e Å⁻³
4428 reflections	Δρ_min = −0.39 e Å⁻³
297 parameters

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
C1	−0.0117 (2)	0.27079 (18)	0.68305 (17)	0.0500 (5)
H1A	−0.0933	0.2146	0.6899	0.075*
H1B	0.0173	0.3008	0.6033	0.075*
H1C	−0.0503	0.3369	0.7262	0.075*
C2	0.13047 (19)	0.20862 (15)	0.72932 (14)	0.0367 (4)
C3	0.27142 (19)	0.18544 (15)	0.66240 (13)	0.0348 (4)
C4	0.27460 (19)	0.22417 (16)	0.54200 (15)	0.0415 (4)
C5	0.42067 (18)	0.12585 (14)	0.69735 (13)	0.0340 (4)
C6	0.4403 (2)	0.08622 (16)	0.81096 (14)	0.0435 (4)
H6	0.3560	0.0959	0.8697	0.052*
C7	0.5842 (2)	0.03238 (17)	0.83791 (15)	0.0459 (4)
H7	0.5942	0.0061	0.9146	0.055*
C8	0.71225 (19)	0.01707 (16)	0.75376 (14)	0.0408 (4)
C9	0.69499 (19)	0.05794 (15)	0.63854 (14)	0.0380 (4)
C10	0.55151 (18)	0.11012 (14)	0.61176 (13)	0.0363 (4)
H10	0.5412	0.1355	0.5350	0.044*
C11	0.8792 (2)	−0.07909 (19)	0.88671 (16)	0.0570 (5)
H11A	0.8578	−0.0153	0.9352	0.086*
H11B	0.9864	−0.1115	0.8881	0.086*
H11C	0.8071	−0.1417	0.9145	0.086*
C12	0.8223 (2)	0.09421 (19)	0.44412 (15)	0.0545 (5)
H12A	0.7447	0.0550	0.4131	0.082*
H12B	0.9246	0.0827	0.3989	0.082*
H12C	0.7933	0.1790	0.4421	0.082*
N1	0.27990 (19)	0.25311 (16)	0.44499 (14)	0.0607 (5)
O1	0.11331 (15)	0.17462 (12)	0.84264 (10)	0.0505 (3)
H1	0.015 (3)	0.1997 (17)	0.8758 (18)	0.061*
O2	0.85876 (14)	−0.03284 (12)	0.77157 (10)	0.0549 (4)
O3	0.82865 (14)	0.04373 (12)	0.56009 (10)	0.0519 (4)
C13	0.4089 (2)	0.77590 (16)	−0.23875 (14)	0.0442 (4)
H13A	0.4517	0.8497	−0.2774	0.066*
H13B	0.3063	0.7933	−0.1962	0.066*
H13C	0.3989	0.7227	−0.2947	0.066*
C14	0.51762 (19)	0.71690 (15)	−0.15769 (14)	0.0361 (4)
C15	0.47497 (18)	0.69111 (15)	−0.04146 (13)	0.0347 (4)
C16	0.3143 (2)	0.72645 (16)	0.00098 (14)	0.0416 (4)
C17	0.57160 (19)	0.62988 (14)	0.04565 (13)	0.0340 (4)
C18	0.50094 (19)	0.61017 (14)	0.16094 (13)	0.0366 (4)
H18	0.3956	0.6370	0.1807	0.044*
C19	0.58282 (19)	0.55206 (15)	0.24623 (13)	0.0377 (4)
C20	0.74174 (19)	0.51091 (15)	0.21806 (14)	0.0378 (4)
C21	0.8120 (2)	0.53047 (17)	0.10525 (15)	0.0476 (5)
H21	0.9174	0.5040	0.0855	0.057*
C22	0.7286 (2)	0.58899 (17)	0.01980 (15)	0.0458 (5)
H22	0.7793	0.6009	−0.0560	0.055*
C23	0.3598 (2)	0.56599 (19)	0.39341 (16)	0.0517 (5)
H23A	0.3456	0.6518	0.3748	0.078*
H23B	0.3316	0.5452	0.4750	0.078*
H23C	0.2932	0.5262	0.3530	0.078*
C24	0.9679 (2)	0.39793 (19)	0.28011 (18)	0.0584 (5)
H24A	0.9636	0.3387	0.2286	0.088*
H24B	1.0046	0.3595	0.3494	0.088*
H24C	1.0396	0.4581	0.2435	0.088*
N2	0.18624 (19)	0.75399 (16)	0.03788 (14)	0.0599 (5)
O4	0.66561 (14)	0.68852 (12)	−0.20565 (11)	0.0493 (3)
H4	0.678 (2)	0.7112 (17)	−0.2832 (19)	0.059*
O5	0.52107 (14)	0.52857 (13)	0.35992 (10)	0.0561 (4)
O6	0.81370 (14)	0.45353 (12)	0.30797 (10)	0.0516 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0338 (9)	0.0654 (12)	0.0469 (11)	0.0104 (8)	−0.0044 (8)	−0.0008 (9)
C2	0.0340 (9)	0.0433 (9)	0.0302 (9)	0.0032 (7)	−0.0028 (7)	0.0003 (7)
C3	0.0313 (8)	0.0427 (9)	0.0279 (8)	0.0034 (7)	−0.0019 (7)	−0.0009 (7)
C4	0.0308 (9)	0.0561 (11)	0.0336 (10)	0.0085 (7)	−0.0025 (7)	0.0004 (8)
C5	0.0309 (8)	0.0402 (9)	0.0289 (8)	0.0021 (7)	−0.0022 (7)	−0.0014 (6)
C6	0.0335 (9)	0.0630 (11)	0.0296 (9)	0.0084 (8)	0.0002 (7)	−0.0006 (8)
C7	0.0425 (10)	0.0656 (12)	0.0261 (9)	0.0059 (8)	−0.0057 (7)	0.0041 (8)
C8	0.0326 (9)	0.0536 (10)	0.0337 (9)	0.0051 (7)	−0.0071 (7)	0.0031 (7)
C9	0.0290 (8)	0.0507 (10)	0.0307 (9)	0.0042 (7)	0.0006 (7)	−0.0005 (7)
C10	0.0335 (9)	0.0489 (10)	0.0231 (8)	0.0047 (7)	−0.0020 (7)	0.0017 (7)
C11	0.0497 (11)	0.0770 (14)	0.0410 (11)	0.0142 (10)	−0.0170 (9)	0.0082 (9)
C12	0.0423 (10)	0.0804 (14)	0.0328 (10)	0.0138 (9)	0.0017 (8)	0.0055 (9)
N1	0.0502 (10)	0.0902 (13)	0.0336 (9)	0.0182 (9)	−0.0030 (7)	0.0076 (8)
O1	0.0365 (7)	0.0771 (9)	0.0312 (7)	0.0129 (6)	0.0028 (5)	0.0012 (6)
O2	0.0359 (7)	0.0865 (10)	0.0362 (7)	0.0166 (6)	−0.0078 (5)	0.0080 (6)
O3	0.0327 (7)	0.0836 (9)	0.0312 (7)	0.0171 (6)	0.0006 (5)	0.0070 (6)
C13	0.0428 (10)	0.0577 (11)	0.0293 (9)	0.0046 (8)	−0.0080 (7)	0.0054 (7)
C14	0.0335 (9)	0.0447 (9)	0.0283 (8)	0.0032 (7)	−0.0048 (7)	0.0002 (7)
C15	0.0306 (8)	0.0442 (9)	0.0266 (8)	0.0046 (7)	−0.0030 (6)	0.0006 (7)
C16	0.0402 (10)	0.0548 (11)	0.0264 (9)	0.0104 (8)	−0.0056 (7)	0.0014 (7)
C17	0.0331 (8)	0.0408 (9)	0.0261 (8)	0.0025 (7)	−0.0033 (6)	−0.0004 (6)
C18	0.0298 (8)	0.0492 (10)	0.0272 (8)	0.0083 (7)	−0.0015 (7)	0.0000 (7)
C19	0.0350 (9)	0.0516 (10)	0.0241 (8)	0.0035 (7)	−0.0026 (7)	−0.0005 (7)
C20	0.0318 (8)	0.0510 (10)	0.0287 (8)	0.0047 (7)	−0.0074 (7)	0.0022 (7)
C21	0.0297 (9)	0.0719 (12)	0.0356 (10)	0.0119 (8)	−0.0009 (7)	0.0018 (8)
C22	0.0347 (9)	0.0694 (12)	0.0269 (9)	0.0095 (8)	0.0013 (7)	0.0052 (8)
C23	0.0391 (10)	0.0775 (13)	0.0313 (9)	0.0137 (9)	0.0012 (8)	0.0041 (8)
C24	0.0365 (10)	0.0782 (14)	0.0547 (12)	0.0152 (9)	−0.0115 (9)	0.0097 (10)
N2	0.0429 (9)	0.0914 (13)	0.0384 (9)	0.0233 (8)	−0.0026 (7)	−0.0009 (8)
O4	0.0370 (7)	0.0786 (9)	0.0244 (6)	0.0107 (6)	0.0021 (5)	0.0080 (6)
O5	0.0376 (7)	0.0963 (10)	0.0253 (6)	0.0189 (6)	0.0001 (5)	0.0099 (6)
O6	0.0355 (7)	0.0800 (9)	0.0339 (7)	0.0143 (6)	−0.0086 (5)	0.0081 (6)

Geometric parameters (Å, º) top

C1—C2	1.494 (2)	C13—C14	1.494 (2)
C1—H1A	0.9600	C13—H13A	0.9600
C1—H1B	0.9600	C13—H13B	0.9600
C1—H1C	0.9600	C13—H13C	0.9600
C2—O1	1.3325 (19)	C14—O4	1.3352 (19)
C2—C3	1.361 (2)	C14—C15	1.364 (2)
C3—C4	1.429 (2)	C15—C16	1.431 (2)
C3—C5	1.483 (2)	C15—C17	1.484 (2)
C4—N1	1.145 (2)	C16—N2	1.147 (2)
C5—C6	1.389 (2)	C17—C22	1.384 (2)
C5—C10	1.403 (2)	C17—C18	1.399 (2)
C6—C7	1.390 (2)	C18—C19	1.380 (2)
C6—H6	0.9300	C18—H18	0.9300
C7—C8	1.376 (2)	C19—O5	1.365 (2)
C7—H7	0.9300	C19—C20	1.403 (2)
C8—O2	1.3654 (19)	C20—O6	1.3722 (19)
C8—C9	1.405 (2)	C20—C21	1.372 (2)
C9—O3	1.3678 (19)	C21—C22	1.390 (2)
C9—C10	1.380 (2)	C21—H21	0.9300
C10—H10	0.9300	C22—H22	0.9300
C11—O2	1.424 (2)	C23—O5	1.419 (2)
C11—H11A	0.9600	C23—H23A	0.9600
C11—H11B	0.9600	C23—H23B	0.9600
C11—H11C	0.9600	C23—H23C	0.9600
C12—O3	1.421 (2)	C24—O6	1.422 (2)
C12—H12A	0.9600	C24—H24A	0.9600
C12—H12B	0.9600	C24—H24B	0.9600
C12—H12C	0.9600	C24—H24C	0.9600
O1—H1	0.91 (2)	O4—H4	0.91 (2)

C2—C1—H1A	109.5	C14—C13—H13A	109.5
C2—C1—H1B	109.5	C14—C13—H13B	109.5
H1A—C1—H1B	109.5	H13A—C13—H13B	109.5
C2—C1—H1C	109.5	C14—C13—H13C	109.5
H1A—C1—H1C	109.5	H13A—C13—H13C	109.5
H1B—C1—H1C	109.5	H13B—C13—H13C	109.5
O1—C2—C3	120.05 (15)	O4—C14—C15	119.68 (14)
O1—C2—C1	116.31 (15)	O4—C14—C13	115.77 (14)
C3—C2—C1	123.64 (15)	C15—C14—C13	124.55 (15)
C2—C3—C4	114.95 (14)	C14—C15—C16	115.05 (14)
C2—C3—C5	128.93 (15)	C14—C15—C17	128.79 (15)
C4—C3—C5	116.11 (14)	C16—C15—C17	116.15 (14)
N1—C4—C3	178.38 (19)	N2—C16—C15	178.22 (18)
C6—C5—C10	117.49 (14)	C22—C17—C18	117.27 (14)
C6—C5—C3	123.81 (14)	C22—C17—C15	123.91 (14)
C10—C5—C3	118.69 (14)	C18—C17—C15	118.81 (14)
C5—C6—C7	120.86 (16)	C19—C18—C17	121.97 (14)
C5—C6—H6	119.6	C19—C18—H18	119.0
C7—C6—H6	119.6	C17—C18—H18	119.0
C8—C7—C6	121.50 (16)	O5—C19—C18	125.13 (14)
C8—C7—H7	119.3	O5—C19—C20	115.04 (14)
C6—C7—H7	119.3	C18—C19—C20	119.82 (15)
O2—C8—C7	125.90 (15)	O6—C20—C21	125.57 (15)
O2—C8—C9	115.71 (14)	O6—C20—C19	115.94 (14)
C7—C8—C9	118.37 (15)	C21—C20—C19	118.49 (14)
O3—C9—C10	124.74 (15)	C20—C21—C22	121.35 (16)
O3—C9—C8	115.17 (14)	C20—C21—H21	119.3
C10—C9—C8	120.07 (15)	C22—C21—H21	119.3
C9—C10—C5	121.70 (15)	C17—C22—C21	121.10 (16)
C9—C10—H10	119.2	C17—C22—H22	119.5
C5—C10—H10	119.2	C21—C22—H22	119.5
O2—C11—H11A	109.5	O5—C23—H23A	109.5
O2—C11—H11B	109.5	O5—C23—H23B	109.5
H11A—C11—H11B	109.5	H23A—C23—H23B	109.5
O2—C11—H11C	109.5	O5—C23—H23C	109.5
H11A—C11—H11C	109.5	H23A—C23—H23C	109.5
H11B—C11—H11C	109.5	H23B—C23—H23C	109.5
O3—C12—H12A	109.5	O6—C24—H24A	109.5
O3—C12—H12B	109.5	O6—C24—H24B	109.5
H12A—C12—H12B	109.5	H24A—C24—H24B	109.5
O3—C12—H12C	109.5	O6—C24—H24C	109.5
H12A—C12—H12C	109.5	H24A—C24—H24C	109.5
H12B—C12—H12C	109.5	H24B—C24—H24C	109.5
C2—O1—H1	109.7 (13)	C14—O4—H4	110.4 (13)
C8—O2—C11	117.32 (14)	C19—O5—C23	117.69 (13)
C9—O3—C12	117.45 (13)	C20—O6—C24	117.18 (14)

O1—C2—C3—C4	178.90 (15)	O4—C14—C15—C16	179.39 (15)
C1—C2—C3—C4	−0.6 (2)	C13—C14—C15—C16	−0.8 (3)
O1—C2—C3—C5	−1.0 (3)	O4—C14—C15—C17	−1.8 (3)
C1—C2—C3—C5	179.46 (17)	C13—C14—C15—C17	178.01 (16)
C2—C3—C5—C6	−2.2 (3)	C14—C15—C17—C22	0.8 (3)
C4—C3—C5—C6	177.82 (16)	C16—C15—C17—C22	179.58 (17)
C2—C3—C5—C10	179.03 (17)	C14—C15—C17—C18	−178.36 (17)
C4—C3—C5—C10	−0.9 (2)	C16—C15—C17—C18	0.5 (2)
C10—C5—C6—C7	−0.4 (3)	C22—C17—C18—C19	−0.2 (3)
C3—C5—C6—C7	−179.17 (17)	C15—C17—C18—C19	178.93 (15)
C5—C6—C7—C8	0.4 (3)	C17—C18—C19—O5	−179.21 (16)
C6—C7—C8—O2	178.91 (17)	C17—C18—C19—C20	0.0 (3)
C6—C7—C8—C9	0.3 (3)	O5—C19—C20—O6	−0.3 (2)
O2—C8—C9—O3	−1.0 (2)	C18—C19—C20—O6	−179.62 (15)
C7—C8—C9—O3	177.74 (16)	O5—C19—C20—C21	179.60 (16)
O2—C8—C9—C10	−179.79 (16)	C18—C19—C20—C21	0.3 (3)
C7—C8—C9—C10	−1.1 (3)	O6—C20—C21—C22	179.56 (17)
O3—C9—C10—C5	−177.60 (15)	C19—C20—C21—C22	−0.4 (3)
C8—C9—C10—C5	1.1 (3)	C18—C17—C22—C21	0.2 (3)
C6—C5—C10—C9	−0.3 (3)	C15—C17—C22—C21	−178.94 (17)
C3—C5—C10—C9	178.48 (15)	C20—C21—C22—C17	0.1 (3)
C7—C8—O2—C11	3.5 (3)	C18—C19—O5—C23	0.4 (3)
C9—C8—O2—C11	−177.88 (16)	C20—C19—O5—C23	−178.84 (16)
C10—C9—O3—C12	4.8 (3)	C21—C20—O6—C24	−7.4 (3)
C8—C9—O3—C12	−173.95 (17)	C19—C20—O6—C24	172.52 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.91 (2)	1.93 (2)	2.835 (2)	173.7 (19)
O4—H4···N1ⁱⁱ	0.91 (2)	1.89 (2)	2.793 (2)	174.3 (19)

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₃NO₃
M_r	219.23
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	8.5316 (13), 11.1801 (17), 11.8021 (18)
α, β, γ (°)	82.777 (3), 81.232 (2), 85.712 (3)
V (Å³)	1102.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.26 × 0.24 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.976, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	6372, 4428, 3078
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.147, 1.03
No. of reflections	4428
No. of parameters	297
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.39

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.91 (2)	1.93 (2)	2.835 (2)	173.7 (19)
O4—H4···N1ⁱⁱ	0.91 (2)	1.89 (2)	2.793 (2)	174.3 (19)

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

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