(E)-Methyl N′-(3-methoxy­benzyl­idene)hydrazinecarboxyl­ate

Lv, L.-P.; Yu, W.-B.; Huang, C.-Y.; Li, W.-W.; Hu, X.-C.

doi:10.1107/S1600536809033194

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2243

doi:10.1107/S1600536809033194

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(E)-Methyl N′-(3-methoxybenzylidene)hydrazinecarboxylate

Lu-Ping Lv,^a Wen-Bo Yu,^a Chun-Yu Huang,^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, ^bThe Children's Hospital of Zhejiang University, School of Medicine, Hangzhou 310003, 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 18 August 2009; accepted 20 August 2009; online 26 August 2009)

The title compound, C₁₀H₁₂N₂O₃, crystallizes with two independent molecules in the asymmetric unit which differ in the orientation of the methoxy group. 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 and N—H⋯N hydrogen bonds. In addition, an intermolecular C—H⋯π interaction is observed.

Related literature

For general background to the properties of benzaldehydehydrazone derivatives, 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

Crystal data

C₁₀H₁₂N₂O₃
M_r = 208.22
Monoclinic, P 2₁ /c
a = 18.207 (3) Å
b = 7.3677 (12) Å
c = 16.552 (3) Å
β = 104.243 (5)°
V = 2152.1 (6) 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
11364 measured reflections
3790 independent reflections
3033 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.109
S = 1.07
3790 reflections
276 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O5	0.86	2.07	2.9188 (18)	172
N4—H4⋯O2ⁱ	0.86	2.25	2.8365 (17)	126
N4—H4⋯N1ⁱ	0.86	2.55	3.3883 (19)	164
C11—H11B⋯Cg1ⁱⁱ	0.96	2.91	3.776 (3)	150
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1. Cg1 is the centroid of the C12–C17 ring.

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/S1600536809033194/ci2891sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809033194/ci2891Isup2.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/C10 and N3/N4/O5/O6/C18/C19/C20 planes form dihedral angles of 4.51 (6)° and 13.80 (6)°, respectively, with the C2—C7 and C12—C17 planes. The dihedral angle between the two independent benzene rings is 59.18 (6)°. Bond lengths and angles are comparable to those observed for methylN'-[(E)-4-methoxybenzylidene]hydrazinecarboxylate (Shang et al., 2007).

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

Related literature top

For general background to the properties of benzaldehydehydrazone derivatives, 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). Cg1 is the centroid of the C12–C17 ring.

Experimental top

3-Methoxybenzaldehyde (1.36 g, 0.01 mol) and methyl hydrazinecarboxylate (0.90 g, 0.01 mol) were dissolved in stirred methanol (20 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. 436–438 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 40% probability level. The dashed line indicates a hydrogen bond.
	Fig. 2. Crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

(E)-Methyl N'-(3-methoxybenzylidene)hydrazinecarboxylate top

Crystal data top

C₁₀H₁₂N₂O₃	F(000) = 880
M_r = 208.22	D_x = 1.285 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3790 reflections
a = 18.207 (3) Å	θ = 2.3–25.0°
b = 7.3677 (12) Å	µ = 0.10 mm⁻¹
c = 16.552 (3) Å	T = 223 K
β = 104.243 (5)°	Block, colourless
V = 2152.1 (6) Å³	0.24 × 0.21 × 0.19 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	3790 independent reflections
Radiation source: fine-focus sealed tube	3033 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −21→18
T_min = 0.977, T_max = 0.989	k = −8→8
11364 measured reflections	l = −19→19

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)] = 0.037	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.054P)² + 0.3311P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.004
3790 reflections	Δρ_max = 0.20 e Å⁻³
276 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0115 (12)

Crystal data top

C₁₀H₁₂N₂O₃	V = 2152.1 (6) Å³
M_r = 208.22	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.207 (3) Å	µ = 0.10 mm⁻¹
b = 7.3677 (12) Å	T = 223 K
c = 16.552 (3) Å	0.24 × 0.21 × 0.19 mm
β = 104.243 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3790 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	3033 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.989	R_int = 0.020
11364 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.07	Δρ_max = 0.20 e Å⁻³
3790 reflections	Δρ_min = −0.17 e Å⁻³
276 parameters

Special details top

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	0.68188 (7)	1.33813 (15)	−0.17091 (7)	0.0626 (3)
O2	0.86739 (7)	0.49630 (16)	−0.12622 (7)	0.0661 (3)
O3	0.92117 (7)	0.34574 (16)	−0.00794 (8)	0.0717 (4)
O4	0.55036 (7)	0.73143 (19)	−0.03581 (8)	0.0788 (4)
O5	0.90715 (7)	0.5763 (2)	0.18325 (7)	0.0792 (4)
O6	0.96333 (6)	0.64573 (18)	0.31586 (7)	0.0690 (4)
N1	0.82614 (7)	0.75999 (16)	−0.02931 (7)	0.0491 (3)
N2	0.86458 (7)	0.60387 (17)	0.00177 (8)	0.0545 (3)
H2	0.8769	0.5836	0.0546	0.065*
N3	0.77335 (7)	0.69523 (16)	0.21361 (7)	0.0492 (3)
N4	0.84157 (7)	0.68885 (19)	0.27209 (8)	0.0574 (4)
H4	0.8442	0.7210	0.3227	0.069*
C1	0.69744 (12)	1.2445 (3)	−0.23962 (10)	0.0724 (5)
H1A	0.6782	1.3132	−0.2896	0.109*
H1B	0.6735	1.1276	−0.2449	0.109*
H1C	0.7512	1.2294	−0.2309	0.109*
C2	0.70930 (8)	1.2656 (2)	−0.09344 (9)	0.0482 (4)
C3	0.70053 (9)	1.3743 (2)	−0.02757 (10)	0.0559 (4)
H3	0.6774	1.4873	−0.0382	0.067*
C4	0.74387 (8)	1.0972 (2)	−0.07774 (9)	0.0478 (4)
H4A	0.7500	1.0249	−0.1217	0.057*
C5	0.72602 (10)	1.3148 (2)	0.05299 (10)	0.0612 (4)
H5	0.7204	1.3879	0.0969	0.073*
C6	0.76013 (9)	1.1460 (2)	0.06930 (10)	0.0567 (4)
H6	0.7768	1.1058	0.1240	0.068*
C7	0.76944 (8)	1.0368 (2)	0.00429 (9)	0.0475 (4)
C8	0.80804 (9)	0.8620 (2)	0.02498 (9)	0.0510 (4)
H8	0.8199	0.8239	0.0802	0.061*
C9	0.88263 (9)	0.4835 (2)	−0.05143 (10)	0.0522 (4)
C10	0.94571 (13)	0.2072 (3)	−0.05631 (15)	0.0888 (6)
H10A	0.9814	0.1291	−0.0201	0.133*
H10B	0.9694	0.2625	−0.0960	0.133*
H10C	0.9028	0.1373	−0.0853	0.133*
C11	0.47641 (11)	0.7249 (3)	−0.09038 (13)	0.0860 (6)
H11A	0.4804	0.7021	−0.1463	0.129*
H11B	0.4513	0.8388	−0.0885	0.129*
H11C	0.4478	0.6293	−0.0731	0.129*
C12	0.55619 (9)	0.7559 (2)	0.04734 (10)	0.0567 (4)
C13	0.49554 (11)	0.7833 (3)	0.08170 (14)	0.0777 (6)
H13	0.4464	0.7862	0.0480	0.093*
C14	0.62919 (9)	0.7513 (2)	0.09829 (10)	0.0518 (4)
H14	0.6700	0.7337	0.0747	0.062*
C15	0.50852 (12)	0.8064 (4)	0.16661 (15)	0.0962 (7)
H15	0.4676	0.8253	0.1899	0.115*
C16	0.58066 (11)	0.8024 (3)	0.21795 (13)	0.0812 (6)
H16	0.5882	0.8194	0.2751	0.097*
C17	0.64204 (9)	0.7725 (2)	0.18355 (10)	0.0531 (4)
C18	0.71842 (9)	0.7617 (2)	0.23885 (10)	0.0528 (4)
H18	0.7269	0.8041	0.2933	0.063*
C19	0.90395 (9)	0.6325 (2)	0.25016 (9)	0.0504 (4)
C20	1.03667 (10)	0.6043 (3)	0.30340 (14)	0.0839 (6)
H20A	1.0750	0.6610	0.3463	0.126*
H20B	1.0401	0.6489	0.2500	0.126*
H20C	1.0441	0.4752	0.3056	0.126*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0750 (8)	0.0619 (7)	0.0499 (6)	0.0148 (6)	0.0135 (5)	0.0052 (5)
O2	0.0832 (8)	0.0608 (7)	0.0546 (7)	0.0141 (6)	0.0177 (6)	0.0080 (5)
O3	0.0808 (9)	0.0605 (7)	0.0716 (8)	0.0215 (6)	0.0150 (6)	0.0188 (6)
O4	0.0582 (8)	0.1052 (10)	0.0640 (8)	0.0062 (7)	−0.0020 (6)	−0.0096 (7)
O5	0.0762 (9)	0.1133 (11)	0.0448 (7)	0.0302 (8)	0.0089 (6)	−0.0079 (7)
O6	0.0538 (7)	0.0895 (9)	0.0555 (7)	0.0082 (6)	−0.0021 (5)	−0.0090 (6)
N1	0.0505 (8)	0.0482 (7)	0.0468 (7)	0.0021 (6)	0.0085 (6)	0.0069 (5)
N2	0.0622 (8)	0.0538 (7)	0.0444 (7)	0.0074 (6)	0.0071 (6)	0.0094 (6)
N3	0.0509 (8)	0.0497 (7)	0.0434 (7)	−0.0003 (6)	0.0045 (6)	−0.0027 (5)
N4	0.0532 (8)	0.0758 (9)	0.0387 (7)	0.0044 (7)	0.0026 (6)	−0.0129 (6)
C1	0.0914 (14)	0.0770 (12)	0.0465 (9)	0.0169 (10)	0.0127 (9)	0.0039 (8)
C2	0.0458 (9)	0.0518 (8)	0.0477 (8)	−0.0018 (7)	0.0126 (6)	0.0009 (6)
C3	0.0568 (10)	0.0507 (8)	0.0629 (10)	0.0035 (7)	0.0201 (8)	−0.0039 (7)
C4	0.0493 (9)	0.0511 (8)	0.0437 (8)	−0.0004 (7)	0.0129 (6)	−0.0042 (6)
C5	0.0685 (11)	0.0645 (10)	0.0544 (10)	0.0014 (9)	0.0226 (8)	−0.0122 (8)
C6	0.0589 (10)	0.0689 (10)	0.0438 (8)	−0.0003 (8)	0.0157 (7)	−0.0013 (7)
C7	0.0432 (8)	0.0536 (8)	0.0468 (8)	−0.0038 (7)	0.0132 (6)	0.0006 (6)
C8	0.0519 (9)	0.0573 (9)	0.0431 (8)	−0.0014 (7)	0.0104 (7)	0.0057 (7)
C9	0.0507 (9)	0.0493 (8)	0.0546 (9)	0.0015 (7)	0.0091 (7)	0.0112 (7)
C10	0.0927 (15)	0.0646 (11)	0.1145 (17)	0.0286 (11)	0.0360 (13)	0.0127 (11)
C11	0.0681 (13)	0.0987 (15)	0.0760 (13)	−0.0005 (11)	−0.0113 (10)	−0.0085 (11)
C12	0.0513 (10)	0.0520 (9)	0.0634 (11)	−0.0023 (7)	0.0077 (8)	−0.0035 (7)
C13	0.0454 (10)	0.0951 (14)	0.0882 (15)	−0.0051 (10)	0.0079 (9)	−0.0067 (11)
C14	0.0457 (9)	0.0492 (8)	0.0596 (9)	−0.0009 (7)	0.0112 (7)	−0.0031 (7)
C15	0.0515 (12)	0.152 (2)	0.0911 (16)	−0.0039 (13)	0.0284 (11)	−0.0137 (15)
C16	0.0600 (12)	0.1185 (17)	0.0685 (12)	−0.0066 (11)	0.0224 (10)	−0.0107 (11)
C17	0.0496 (9)	0.0503 (8)	0.0601 (10)	−0.0052 (7)	0.0149 (7)	−0.0030 (7)
C18	0.0571 (10)	0.0539 (9)	0.0467 (8)	−0.0048 (7)	0.0116 (7)	−0.0053 (7)
C19	0.0565 (10)	0.0491 (8)	0.0414 (8)	0.0052 (7)	0.0044 (7)	0.0021 (6)
C20	0.0541 (12)	0.0970 (15)	0.0941 (15)	0.0160 (10)	0.0058 (10)	0.0073 (12)

Geometric parameters (Å, º) top

O1—C2	1.3654 (18)	C5—C6	1.387 (2)
O1—C1	1.417 (2)	C5—H5	0.93
O2—C9	1.2039 (18)	C6—C7	1.387 (2)
O3—C9	1.3387 (18)	C6—H6	0.93
O3—C10	1.435 (2)	C7—C8	1.467 (2)
O4—C12	1.366 (2)	C8—H8	0.93
O4—C11	1.426 (2)	C10—H10A	0.96
O5—C19	1.1971 (18)	C10—H10B	0.96
O6—C19	1.3351 (18)	C10—H10C	0.96
O6—C20	1.433 (2)	C11—H11A	0.96
N1—C8	1.2757 (19)	C11—H11B	0.96
N1—N2	1.3785 (17)	C11—H11C	0.96
N2—C9	1.346 (2)	C12—C13	1.376 (3)
N2—H2	0.86	C12—C14	1.388 (2)
N3—C18	1.273 (2)	C13—C15	1.377 (3)
N3—N4	1.3749 (17)	C13—H13	0.93
N4—C19	1.341 (2)	C14—C17	1.381 (2)
N4—H4	0.86	C14—H14	0.93
C1—H1A	0.96	C15—C16	1.378 (3)
C1—H1B	0.96	C15—H15	0.93
C1—H1C	0.96	C16—C17	1.391 (2)
C2—C4	1.386 (2)	C16—H16	0.93
C2—C3	1.393 (2)	C17—C18	1.467 (2)
C3—C5	1.372 (2)	C18—H18	0.93
C3—H3	0.93	C20—H20A	0.96
C4—C7	1.396 (2)	C20—H20B	0.96
C4—H4A	0.93	C20—H20C	0.96

C2—O1—C1	117.64 (12)	O3—C10—H10A	109.5
C9—O3—C10	115.68 (14)	O3—C10—H10B	109.5
C12—O4—C11	118.03 (15)	H10A—C10—H10B	109.5
C19—O6—C20	117.62 (14)	O3—C10—H10C	109.5
C8—N1—N2	115.11 (12)	H10A—C10—H10C	109.5
C9—N2—N1	119.26 (12)	H10B—C10—H10C	109.5
C9—N2—H2	120.4	O4—C11—H11A	109.5
N1—N2—H2	120.4	O4—C11—H11B	109.5
C18—N3—N4	115.39 (13)	H11A—C11—H11B	109.5
C19—N4—N3	119.91 (12)	O4—C11—H11C	109.5
C19—N4—H4	120.0	H11A—C11—H11C	109.5
N3—N4—H4	120.0	H11B—C11—H11C	109.5
O1—C1—H1A	109.5	O4—C12—C13	124.38 (16)
O1—C1—H1B	109.5	O4—C12—C14	115.73 (15)
H1A—C1—H1B	109.5	C13—C12—C14	119.90 (16)
O1—C1—H1C	109.5	C12—C13—C15	119.10 (17)
H1A—C1—H1C	109.5	C12—C13—H13	120.4
H1B—C1—H1C	109.5	C15—C13—H13	120.4
O1—C2—C4	124.80 (13)	C17—C14—C12	120.93 (16)
O1—C2—C3	115.07 (13)	C17—C14—H14	119.5
C4—C2—C3	120.13 (14)	C12—C14—H14	119.5
C5—C3—C2	120.02 (15)	C13—C15—C16	121.65 (19)
C5—C3—H3	120.0	C13—C15—H15	119.2
C2—C3—H3	120.0	C16—C15—H15	119.2
C2—C4—C7	119.68 (14)	C15—C16—C17	119.41 (19)
C2—C4—H4A	120.2	C15—C16—H16	120.3
C7—C4—H4A	120.2	C17—C16—H16	120.3
C3—C5—C6	120.27 (15)	C14—C17—C16	119.00 (16)
C3—C5—H5	119.9	C14—C17—C18	121.84 (15)
C6—C5—H5	119.9	C16—C17—C18	119.15 (16)
C7—C6—C5	120.23 (15)	N3—C18—C17	121.13 (14)
C7—C6—H6	119.9	N3—C18—H18	119.4
C5—C6—H6	119.9	C17—C18—H18	119.4
C6—C7—C4	119.66 (14)	O5—C19—O6	124.39 (15)
C6—C7—C8	118.10 (13)	O5—C19—N4	126.52 (14)
C4—C7—C8	122.22 (14)	O6—C19—N4	109.08 (13)
N1—C8—C7	123.03 (13)	O6—C20—H20A	109.5
N1—C8—H8	118.5	O6—C20—H20B	109.5
C7—C8—H8	118.5	H20A—C20—H20B	109.5
O2—C9—O3	124.75 (15)	O6—C20—H20C	109.5
O2—C9—N2	126.11 (14)	H20A—C20—H20C	109.5
O3—C9—N2	109.14 (13)	H20B—C20—H20C	109.5

C8—N1—N2—C9	176.68 (14)	N1—N2—C9—O3	178.40 (12)
C18—N3—N4—C19	−175.58 (14)	C11—O4—C12—C13	−3.2 (3)
C1—O1—C2—C4	−7.6 (2)	C11—O4—C12—C14	176.59 (15)
C1—O1—C2—C3	172.35 (15)	O4—C12—C13—C15	180.0 (2)
O1—C2—C3—C5	179.99 (15)	C14—C12—C13—C15	0.2 (3)
C4—C2—C3—C5	−0.1 (2)	O4—C12—C14—C17	−179.29 (14)
O1—C2—C4—C7	−179.72 (14)	C13—C12—C14—C17	0.5 (2)
C3—C2—C4—C7	0.4 (2)	C12—C13—C15—C16	−0.2 (4)
C2—C3—C5—C6	−0.4 (3)	C13—C15—C16—C17	−0.6 (4)
C3—C5—C6—C7	0.7 (3)	C12—C14—C17—C16	−1.3 (2)
C5—C6—C7—C4	−0.4 (2)	C12—C14—C17—C18	177.79 (14)
C5—C6—C7—C8	178.06 (15)	C15—C16—C17—C14	1.3 (3)
C2—C4—C7—C6	−0.1 (2)	C15—C16—C17—C18	−177.8 (2)
C2—C4—C7—C8	−178.51 (13)	N4—N3—C18—C17	−178.49 (13)
N2—N1—C8—C7	177.72 (13)	C14—C17—C18—N3	−15.0 (2)
C6—C7—C8—N1	−172.84 (15)	C16—C17—C18—N3	164.04 (17)
C4—C7—C8—N1	5.6 (2)	C20—O6—C19—O5	5.5 (2)
C10—O3—C9—O2	0.7 (2)	C20—O6—C19—N4	−175.48 (15)
C10—O3—C9—N2	−178.90 (15)	N3—N4—C19—O5	−3.8 (3)
N1—N2—C9—O2	−1.2 (2)	N3—N4—C19—O6	177.20 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5	0.86	2.07	2.9188 (18)	172
N4—H4···O2ⁱ	0.86	2.25	2.8365 (17)	126
N4—H4···N1ⁱ	0.86	2.55	3.3883 (19)	164
C11—H11B···Cg1ⁱⁱ	0.96	2.91	3.776 (3)	150

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+1.

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)	18.207 (3), 7.3677 (12), 16.552 (3)
β (°)	104.243 (5)
V (Å³)	2152.1 (6)
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	11364, 3790, 3033
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.109, 1.07
No. of reflections	3790
No. of parameters	276
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.17

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—H2···O5	0.86	2.07	2.9188 (18)	172
N4—H4···O2ⁱ	0.86	2.25	2.8365 (17)	126
N4—H4···N1ⁱ	0.86	2.55	3.3883 (19)	164
C11—H11B···Cg1ⁱⁱ	0.96	2.91	3.776 (3)	150

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+1.

Acknowledgements

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

References

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