Methyl N′-[(E)-2-methoxy­benzyl­idene]­hydrazinecarboxyl­ate

Lv, L.-P.; Yu, W.-B.; Lu, Z.-H.; Li, W.-W.; Hu, X.-C.

doi:10.1107/S1600536809014172

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1085

doi:10.1107/S1600536809014172

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Methyl N′-[(E)-2-methoxybenzylidene]hydrazinecarboxylate

Lu-Ping Lv,^a Wen-Bo Yu,^a Zhong-Hao Lu,^b Wei-Wei Li ^a and Xian-Chao Hu ^c ^*

^aDepartment of Chemical Engineering, Hangzhou Vocational and Technical College, Hangzhou 310018, People's Republic of China, ^bAir Liquide (Hangzhou) Co. Ltd, Hangzhou 311112, People's Republic of China, and ^cResearch Center of Analysis and Measurement, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: zgdhxc@126.com

(Received 10 April 2009; accepted 16 April 2009; online 22 April 2009)

The title compound, C₁₀H₁₂N₂O₃, crystallizes with two independent molecules in the asymmetric unit. The side chains in the two independent molecules have slightly different orientations, with the C=N—N—C torsion angle being 169.19 (14)° in one of the molecules and −179.86 (14)° in the other. Each independent molecule adopts a trans configuration with respect to the C=N bond. In the crystal structure, molecules are linked into chains running along [001] by N—H⋯O, N—H⋯N and C—H⋯O hydrogen bonds. In addition, an intermolecular C—H⋯π interaction is observed.

Related literature

For applications of benzaldehydehydrazone derviatives, see: Parashar et al. (1988 ); Hadjoudis et al. (1987 ); Borg et al. (1999 ). For metal complexes of Schiff base ligands, see: Kahwa et al. (1986 ); Santos et al. (2001 ). For a related structure, see: Shang et al. (2007 ).

Experimental

Crystal data

C₁₀H₁₂N₂O₃
M_r = 208.22
Monoclinic, P 2₁ /c
a = 17.221 (5) Å
b = 7.442 (2) Å
c = 16.611 (6) Å
β = 95.423 (12)°
V = 2119.4 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 223 K
0.24 × 0.21 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.977, T_max = 0.989
11064 measured reflections
3723 independent reflections
2834 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.120
S = 1.08
3723 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12–C17 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O5	0.86	2.08	2.938 (2)	173
N4—H4N⋯N1ⁱ	0.86	2.42	3.279 (2)	177
C1—H1A⋯O2ⁱ	0.96	2.52	3.472 (2)	170
C11—H11B⋯Cg1ⁱⁱ	0.96	2.87	3.826 (3)	175
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809014172/ci2777sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809014172/ci2777Isup2.hkl

checkCIF report

Comment top

Benzaldehydehydrazone derivatives have attracted much attention due to their pharmacological activity (Parashar et al., 1988) and their photochromic properties (Hadjoudis et al., 1987). They are important intermediates of 1,3,4-oxadiazoles, which have been reported to be versatile compounds with many interesting properties (Borg et al., 1999). Metal complexes based on Schiff bases have received considerable attention because they can be utilized as model compounds of active centres in various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). We report here the crystal structure of the title compound (Fig. 1).

The title compound contains two independent, but almost identical molecules in the asymmetric unit. Each independent molecule adopts a trans configuration with respect to the C═N bond. The N1/N2/O2/O3/C8/C9 and N3/N4/O5/O6/C18/C19 planes form dihedral angles of 3.20 (6)° and 11.61 (5)°, respectively, with the C2—C7 and C12—C17 planes. The dihedral angle between the two independent benzene rings is 49.19 (7)°. The bond lengths and angles are comparable to those observed for methylN'-[(E)-4-methoxybenzylidene]hydrazinecarboxylate (Shang et al., 2007).

In the crystal structure, the molecules are linked into chains running along the [001] by N—H···O, N—H···N and C—H···O hydrogen bonds. In addition, an intermolecular C—H···π interaction is observed (Table 1).

Related literature top

For general background, see: Parashar et al. (1988); Hadjoudis et al. (1987); Borg et al. (1999); Kahwa et al. (1986); Santos et al. (2001). For a related structure, see: Shang et al. (2007).

Experimental top

2-Methoxybenzaldehyde (1.36 g, 0.01 mol) and methyl hydrazinecarboxylate (0.90 g, 0.01 mol) were dissolved in stirred methanol (25 ml) and left for 2.5 h at room temperature. The resulting solid was filtered off and recrystallized from ethanol to give the title compound in 95% yield. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature (m.p. 428–430 K).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. Dashed lines indicate hydrogen bonds.
	Fig. 2. Crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

Methyl N'-[(E)-2-methoxybenzylidene]hydrazinecarboxylate top

Crystal data top

C₁₀H₁₂N₂O₃	F(000) = 880
M_r = 208.22	D_x = 1.305 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3723 reflections
a = 17.221 (5) Å	θ = 1.2–25.0°
b = 7.442 (2) Å	µ = 0.10 mm⁻¹
c = 16.611 (6) Å	T = 223 K
β = 95.423 (12)°	Block, colourless
V = 2119.4 (12) Å³	0.24 × 0.21 × 0.19 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	3723 independent reflections
Radiation source: fine-focus sealed tube	2834 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −20→20
T_min = 0.977, T_max = 0.989	k = −8→8
11064 measured reflections	l = −19→18

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0639P)² + 0.1492P] where P = (F_o² + 2F_c²)/3
3723 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₀H₁₂N₂O₃	V = 2119.4 (12) Å³
M_r = 208.22	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.221 (5) Å	µ = 0.10 mm⁻¹
b = 7.442 (2) Å	T = 223 K
c = 16.611 (6) Å	0.24 × 0.21 × 0.19 mm
β = 95.423 (12)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3723 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2834 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.989	R_int = 0.026
11064 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.08	Δρ_max = 0.21 e Å⁻³
3723 reflections	Δρ_min = −0.18 e Å⁻³
271 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
O1	0.27964 (7)	−0.12236 (16)	0.66716 (7)	0.0579 (3)
O3	0.41712 (7)	0.63135 (17)	0.50573 (7)	0.0644 (4)
O2	0.36311 (7)	0.49059 (17)	0.39394 (7)	0.0649 (4)
O6	0.45355 (6)	0.3646 (2)	0.82317 (7)	0.0676 (4)
O4	0.06692 (7)	0.15183 (19)	0.84498 (9)	0.0716 (4)
N3	0.26187 (7)	0.29235 (18)	0.74487 (8)	0.0478 (3)
O5	0.40316 (7)	0.3884 (2)	0.69432 (8)	0.0733 (4)
N1	0.31881 (7)	0.21928 (19)	0.49137 (8)	0.0483 (3)
N2	0.35854 (8)	0.37207 (19)	0.51936 (8)	0.0522 (4)
H2N	0.3707	0.3869	0.5703	0.063*
N4	0.32825 (7)	0.3208 (2)	0.79597 (8)	0.0525 (4)
H4N	0.3270	0.3140	0.8475	0.063*
C7	0.26100 (8)	−0.0607 (2)	0.52867 (9)	0.0460 (4)
C17	0.13105 (9)	0.1853 (2)	0.72717 (11)	0.0506 (4)
C18	0.20343 (9)	0.2284 (2)	0.77764 (10)	0.0497 (4)
H18	0.2067	0.2093	0.8332	0.060*
C8	0.30274 (8)	0.1085 (2)	0.54641 (10)	0.0479 (4)
H8	0.3183	0.1366	0.6001	0.057*
C9	0.37808 (9)	0.4974 (2)	0.46625 (10)	0.0492 (4)
C16	0.12959 (10)	0.1783 (3)	0.64363 (12)	0.0616 (5)
H16	0.1746	0.2063	0.6194	0.074*
C4	0.18349 (10)	−0.3883 (3)	0.50054 (12)	0.0635 (5)
H4	0.1581	−0.4976	0.4910	0.076*
C3	0.21174 (10)	−0.3421 (2)	0.57816 (11)	0.0569 (5)
H3	0.2052	−0.4199	0.6208	0.068*
C5	0.19269 (10)	−0.2740 (3)	0.43723 (11)	0.0630 (5)
H5	0.1730	−0.3054	0.3851	0.076*
C1	0.26395 (13)	−0.2246 (3)	0.73518 (11)	0.0735 (6)
H1A	0.2882	−0.1691	0.7833	0.110*
H1B	0.2843	−0.3438	0.7304	0.110*
H1C	0.2086	−0.2306	0.7382	0.110*
C2	0.25007 (8)	−0.1791 (2)	0.59263 (10)	0.0470 (4)
C20	0.53167 (10)	0.3890 (3)	0.80043 (15)	0.0834 (7)
H20A	0.5678	0.3901	0.8481	0.125*
H20B	0.5348	0.5010	0.7722	0.125*
H20C	0.5444	0.2922	0.7658	0.125*
C10	0.44366 (12)	0.7734 (3)	0.45624 (14)	0.0771 (6)
H10A	0.4707	0.8621	0.4901	0.116*
H10B	0.3997	0.8279	0.4258	0.116*
H10C	0.4783	0.7247	0.4198	0.116*
C6	0.23130 (10)	−0.1116 (3)	0.45094 (11)	0.0578 (5)
H6	0.2375	−0.0354	0.4076	0.069*
C14	−0.00378 (13)	0.0922 (3)	0.63078 (16)	0.0853 (7)
H14	−0.0489	0.0620	0.5984	0.102*
C19	0.39555 (9)	0.3595 (2)	0.76374 (10)	0.0477 (4)
C13	−0.00495 (11)	0.0976 (3)	0.71332 (16)	0.0752 (6)
H13	−0.0507	0.0708	0.7365	0.090*
C12	0.06241 (9)	0.1433 (2)	0.76246 (12)	0.0582 (5)
C15	0.06312 (12)	0.1308 (3)	0.59552 (14)	0.0783 (6)
H15	0.0636	0.1250	0.5396	0.094*
C11	−0.00264 (13)	0.1165 (3)	0.88362 (16)	0.0942 (8)
H11A	0.0085	0.1268	0.9412	0.141*
H11B	−0.0208	−0.0028	0.8703	0.141*
H11C	−0.0422	0.2019	0.8652	0.141*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0726 (7)	0.0557 (8)	0.0444 (7)	−0.0051 (6)	0.0008 (5)	0.0033 (5)
O3	0.0752 (8)	0.0550 (8)	0.0625 (8)	−0.0139 (6)	0.0050 (6)	−0.0052 (6)
O2	0.0852 (8)	0.0594 (9)	0.0491 (8)	−0.0064 (6)	0.0008 (6)	0.0032 (6)
O6	0.0470 (6)	0.0963 (11)	0.0579 (8)	−0.0085 (6)	−0.0042 (5)	0.0026 (7)
O4	0.0582 (7)	0.0764 (10)	0.0818 (10)	−0.0074 (6)	0.0150 (6)	0.0087 (7)
N3	0.0471 (7)	0.0452 (8)	0.0496 (8)	0.0012 (6)	−0.0030 (6)	0.0025 (6)
O5	0.0682 (8)	0.1061 (12)	0.0457 (8)	−0.0207 (7)	0.0058 (6)	0.0028 (7)
N1	0.0514 (7)	0.0468 (9)	0.0464 (8)	0.0006 (6)	0.0027 (6)	−0.0005 (7)
N2	0.0624 (8)	0.0539 (10)	0.0392 (7)	−0.0041 (7)	−0.0002 (6)	−0.0016 (6)
N4	0.0462 (7)	0.0693 (10)	0.0408 (7)	−0.0045 (6)	−0.0018 (6)	0.0058 (7)
C7	0.0417 (8)	0.0506 (10)	0.0461 (9)	0.0046 (7)	0.0065 (6)	−0.0014 (8)
C17	0.0474 (8)	0.0382 (10)	0.0648 (11)	0.0069 (7)	−0.0018 (7)	−0.0028 (8)
C18	0.0489 (9)	0.0466 (10)	0.0528 (10)	0.0038 (7)	0.0009 (7)	0.0009 (8)
C8	0.0482 (8)	0.0540 (11)	0.0416 (9)	0.0036 (7)	0.0047 (7)	−0.0010 (8)
C9	0.0526 (9)	0.0483 (11)	0.0462 (10)	0.0050 (7)	0.0021 (7)	−0.0018 (8)
C16	0.0562 (10)	0.0587 (12)	0.0681 (12)	0.0111 (8)	−0.0036 (8)	−0.0107 (9)
C4	0.0579 (10)	0.0629 (13)	0.0704 (13)	−0.0092 (9)	0.0093 (9)	−0.0139 (10)
C3	0.0579 (10)	0.0535 (12)	0.0605 (11)	−0.0032 (8)	0.0110 (8)	0.0008 (9)
C5	0.0601 (10)	0.0758 (14)	0.0525 (11)	−0.0061 (9)	0.0012 (8)	−0.0149 (10)
C1	0.1031 (15)	0.0659 (14)	0.0504 (11)	−0.0079 (11)	0.0014 (10)	0.0094 (10)
C2	0.0439 (8)	0.0485 (10)	0.0488 (10)	0.0050 (7)	0.0058 (7)	−0.0025 (8)
C20	0.0483 (10)	0.0993 (18)	0.1017 (17)	−0.0118 (10)	0.0030 (10)	−0.0090 (14)
C10	0.0798 (13)	0.0608 (14)	0.0931 (16)	−0.0161 (10)	0.0202 (12)	−0.0003 (11)
C6	0.0569 (10)	0.0692 (13)	0.0477 (10)	−0.0006 (9)	0.0067 (8)	−0.0018 (9)
C14	0.0684 (13)	0.0708 (15)	0.1093 (19)	0.0035 (11)	−0.0308 (13)	−0.0254 (13)
C19	0.0511 (9)	0.0468 (10)	0.0441 (10)	−0.0031 (7)	−0.0004 (7)	−0.0015 (7)
C13	0.0499 (10)	0.0543 (13)	0.119 (2)	−0.0044 (9)	−0.0018 (11)	−0.0084 (12)
C12	0.0512 (9)	0.0415 (11)	0.0810 (14)	0.0022 (7)	0.0016 (9)	−0.0019 (9)
C15	0.0744 (13)	0.0752 (16)	0.0804 (14)	0.0126 (11)	−0.0187 (11)	−0.0219 (12)
C11	0.0803 (14)	0.0885 (18)	0.119 (2)	−0.0205 (12)	0.0373 (13)	0.0061 (15)

Geometric parameters (Å, º) top

O1—C2	1.3605 (19)	C16—H16	0.93
O1—C1	1.409 (2)	C4—C5	1.374 (3)
O3—C9	1.339 (2)	C4—C3	1.378 (3)
O3—C10	1.440 (2)	C4—H4	0.93
O2—C9	1.205 (2)	C3—C2	1.391 (2)
O6—C19	1.3370 (19)	C3—H3	0.93
O6—C20	1.443 (2)	C5—C6	1.388 (3)
O4—C12	1.367 (2)	C5—H5	0.93
O4—C11	1.436 (2)	C1—H1A	0.96
N3—C18	1.280 (2)	C1—H1B	0.96
N3—N4	1.3742 (17)	C1—H1C	0.96
O5—C19	1.1922 (19)	C20—H20A	0.96
N1—C8	1.281 (2)	C20—H20B	0.96
N1—N2	1.3846 (19)	C20—H20C	0.96
N2—C9	1.348 (2)	C10—H10A	0.96
N2—H2N	0.86	C10—H10B	0.96
N4—C19	1.353 (2)	C10—H10C	0.96
N4—H4N	0.86	C6—H6	0.93
C7—C6	1.395 (2)	C14—C15	1.371 (3)
C7—C2	1.406 (2)	C14—C13	1.374 (3)
C7—C8	1.466 (2)	C14—H14	0.93
C17—C16	1.386 (3)	C13—C12	1.396 (3)
C17—C12	1.403 (2)	C13—H13	0.93
C17—C18	1.471 (2)	C15—H15	0.93
C18—H18	0.93	C11—H11A	0.96
C8—H8	0.93	C11—H11B	0.96
C16—C15	1.379 (3)	C11—H11C	0.96

C2—O1—C1	118.57 (14)	O1—C1—H1C	109.5
C9—O3—C10	116.02 (15)	H1A—C1—H1C	109.5
C19—O6—C20	117.40 (15)	H1B—C1—H1C	109.5
C12—O4—C11	117.97 (16)	O1—C2—C3	123.94 (16)
C18—N3—N4	115.85 (13)	O1—C2—C7	115.33 (14)
C8—N1—N2	114.99 (13)	C3—C2—C7	120.73 (15)
C9—N2—N1	119.64 (13)	O6—C20—H20A	109.5
C9—N2—H2N	120.2	O6—C20—H20B	109.5
N1—N2—H2N	120.2	H20A—C20—H20B	109.5
C19—N4—N3	118.82 (13)	O6—C20—H20C	109.5
C19—N4—H4N	120.6	H20A—C20—H20C	109.5
N3—N4—H4N	120.6	H20B—C20—H20C	109.5
C6—C7—C2	117.76 (16)	O3—C10—H10A	109.5
C6—C7—C8	123.29 (16)	O3—C10—H10B	109.5
C2—C7—C8	118.96 (14)	H10A—C10—H10B	109.5
C16—C17—C12	118.26 (16)	O3—C10—H10C	109.5
C16—C17—C18	120.86 (16)	H10A—C10—H10C	109.5
C12—C17—C18	120.84 (16)	H10B—C10—H10C	109.5
N3—C18—C17	119.80 (15)	C5—C6—C7	121.06 (17)
N3—C18—H18	120.1	C5—C6—H6	119.5
C17—C18—H18	120.1	C7—C6—H6	119.5
N1—C8—C7	122.99 (15)	C15—C14—C13	120.82 (19)
N1—C8—H8	118.5	C15—C14—H14	119.6
C7—C8—H8	118.5	C13—C14—H14	119.6
O2—C9—O3	124.73 (16)	O5—C19—O6	124.49 (15)
O2—C9—N2	125.42 (16)	O5—C19—N4	126.70 (14)
O3—C9—N2	109.84 (14)	O6—C19—N4	108.79 (14)
C15—C16—C17	121.7 (2)	C14—C13—C12	120.1 (2)
C15—C16—H16	119.2	C14—C13—H13	120.0
C17—C16—H16	119.2	C12—C13—H13	120.0
C5—C4—C3	120.38 (18)	O4—C12—C13	124.25 (18)
C5—C4—H4	119.8	O4—C12—C17	116.00 (15)
C3—C4—H4	119.8	C13—C12—C17	119.75 (19)
C4—C3—C2	119.93 (17)	C14—C15—C16	119.4 (2)
C4—C3—H3	120.0	C14—C15—H15	120.3
C2—C3—H3	120.0	C16—C15—H15	120.3
C4—C5—C6	120.14 (17)	O4—C11—H11A	109.5
C4—C5—H5	119.9	O4—C11—H11B	109.5
C6—C5—H5	119.9	H11A—C11—H11B	109.5
O1—C1—H1A	109.5	O4—C11—H11C	109.5
O1—C1—H1B	109.5	H11A—C11—H11C	109.5
H1A—C1—H1B	109.5	H11B—C11—H11C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O5	0.86	2.08	2.938 (2)	173
N4—H4N···N1ⁱ	0.86	2.42	3.279 (2)	177
C1—H1A···O2ⁱ	0.96	2.52	3.472 (2)	170
C11—H11B···Cg1ⁱⁱ	0.96	2.87	3.826 (3)	175

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂N₂O₃
M_r	208.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	223
a, b, c (Å)	17.221 (5), 7.442 (2), 16.611 (6)
β (°)	95.423 (12)
V (Å³)	2119.4 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.24 × 0.21 × 0.19

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.977, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	11064, 3723, 2834
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.120, 1.08
No. of reflections	3723
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.18

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O5	0.86	2.08	2.938 (2)	173
N4—H4N···N1ⁱ	0.86	2.42	3.279 (2)	177
C1—H1A···O2ⁱ	0.96	2.52	3.472 (2)	170
C11—H11B···Cg1ⁱⁱ	0.96	2.87	3.826 (3)	175

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

Acknowledgements

The authors thank the Science and Technology Project of Zhejiang Province (grant No. 2007 F70077) for financial support.

References

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