(E)-Methyl N′-(3,4-dimethoxy­benzyl­idene)hydrazinecarboxyl­ate

Lv, L.-P.; Ding, X.-M.; Zhang, Y.-Z.; Li, W.-W.; Hu, X.-C.

doi:10.1107/S1600536808034260

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2189

doi:10.1107/S1600536808034260

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(E)-Methyl N′-(3,4-dimethoxybenzylidene)hydrazinecarboxylate

Lu-Ping Lv,^a Xiao-Min Ding,^a Yong-Zhao Zhang,^a Wei-Wei Li ^a and Xian-Chao Hu ^b ^*

^aDepartment of Chemical Engineering, Hangzhou Vocational and Technical College, Hangzhou 310018, People's Republic of China, and ^bResearch Center of Analysis and Measurement, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: zgdhxc@126.com

(Received 8 October 2008; accepted 20 October 2008; online 25 October 2008)

The title compound, C₁₁H₁₄N₂O₄, crystallizes with two independent but essentially identical molecules in the asymmetric unit. Each molecule adopts a trans configuration with respect to the C=N bond. Molecules are linked into a one-dimensional network by inter- and intramolecular N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C₁₁H₁₄N₂O₄
M_r = 238.24
Triclinic, P 1
a = 8.5276 (11) Å
b = 8.5517 (11) Å
c = 8.6259 (11) Å
α = 92.919 (5)°
β = 94.209 (4)°
γ = 94.146 (5)°
V = 624.71 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 273 (2) K
0.23 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.971, T_max = 0.979
3471 measured reflections
2172 independent reflections
1985 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.080
S = 1.04
2172 reflections
314 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.10 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O5ⁱ	0.86	2.07	2.902 (3)	164
N2—H2⋯O6ⁱ	0.86	2.54	3.153 (3)	129
N4—H4A⋯O3	0.86	2.13	2.968 (3)	164
C19—H19⋯O2ⁱⁱ	0.93	2.55	3.337 (3)	143
C13—H13A⋯Cg1ⁱⁱⁱ	0.96	2.94	3.531 (4)	121
Symmetry codes: (i) x, y-1, z+1; (ii) x+1, y, z; (iii) x, y, z-1. Cg1 is the centroid of the C3–C8 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/S1600536808034260/bg2215sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808034260/bg2215Isup2.hkl

checkCIF report

Comment top

Benzaldehydehydrazone derivatives have received considerable attentions for a long time due to their pharmacological activity (Parashar et al., 1988) and their photochromic properties(Hadjoudis et al., 1987). Meanwhile, it's an important intermidiate of 1,3,4-oxadiazoles, which have been reported to be versatile compounds with many properties(Borg et al., 1999). As a further investigation of this type of derivatives, we report herein the crystal structure of the title compound (I).

The title compound, C₁₁H₁₄N₂O₄ ,crystallizes with two independent, but essentially identical molecules in the asymmetric unit. Each essentially planar molecule of the unit adopts a trans configuration with respect to the C═N bond. in a molecule of the unit,the hydrazine carboxylic acid methyl ester group is slightly twisted away from the attached ring. The dihedral angle between the two essentially planar molecule of the unit is 81.67 (4)°. The bond lengths and angles agree with those observed for (E)-Methyl N'-(4-hydroxybenzylidene)hydrazinecarboxylate (Shang et al., 2007).

The molecules are linked into a one-dimensional network by intermolecular intramolecular N–H···O, C–H···O hydrogen bonds (Fig.2). Meanwhile, A C—H···π contact between benzene ring (centroid Cg1) and H atom of methoxy C13 further stabilizes the structure (Table 1).

Related literature top

For general background, see: Parashar et al. (1988); Hadjoudis et al. (1987); Borg et al. (1999). For a related structure, see: Shang et al. (2007). Cg1 is the centroid of the C3–C8 ring.

Experimental top

3,4-Dimethoxybenzaldehyde (1.66 g, 0.01 mol) and methyl hydrazinecarboxylate (0.9g, 0.01mol) were dissolved in stirred methanol (25ml) and left for 3.2h at room temperature. The resulting solid was filtered off and recrystallized from ethanol to give the title compound in 86% yield. Crystals suitable for X-ray analysis were obtained by slow evaporation of a ethanol solution at room temperature (m.p. 468-470 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. Molecular structure of (I), showing 20% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. Crystal packing of the title compound, viewed approximately down the a axis. Dashed lines indicate hydrogen bonds. H atoms not intervening in H-bonding were eliminated for clarity.

(E)-Methyl N'-(3,4-dimethoxybenzylidene)hydrazinecarboxylate top

Crystal data top

C₁₁H₁₄N₂O₄	Z = 2
M_r = 238.24	F(000) = 252
Triclinic, P1	D_x = 1.267 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5276 (11) Å	Cell parameters from 2172 reflections
b = 8.5517 (11) Å	θ = 2.4–25.0°
c = 8.6259 (11) Å	µ = 0.10 mm⁻¹
α = 92.919 (5)°	T = 273 K
β = 94.209 (4)°	Block, colourless
γ = 94.146 (5)°	0.23 × 0.21 × 0.20 mm
V = 624.71 (14) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2172 independent reflections
Radiation source: fine-focus sealed tube	1985 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→10
T_min = 0.971, T_max = 0.979	k = −10→9
3471 measured reflections	l = −10→10

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)] = 0.028	H-atom parameters constrained
wR(F²) = 0.080	w = 1/[σ²(F_o²) + (0.049P)² + 0.0326P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.010
2172 reflections	Δρ_max = 0.11 e Å⁻³
314 parameters	Δρ_min = −0.10 e Å⁻³
3 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: 0.034 (6)

Crystal data top

C₁₁H₁₄N₂O₄	γ = 94.146 (5)°
M_r = 238.24	V = 624.71 (14) Å³
Triclinic, P1	Z = 2
a = 8.5276 (11) Å	Mo Kα radiation
b = 8.5517 (11) Å	µ = 0.10 mm⁻¹
c = 8.6259 (11) Å	T = 273 K
α = 92.919 (5)°	0.23 × 0.21 × 0.20 mm
β = 94.209 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2172 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1985 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.979	R_int = 0.013
3471 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	3 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.04	Δρ_max = 0.11 e Å⁻³
2172 reflections	Δρ_min = −0.10 e Å⁻³
314 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
C1	−0.1778 (4)	0.3653 (5)	0.7975 (4)	0.0950 (11)
H1A	−0.2261	0.2682	0.8289	0.143*
H1B	−0.2577	0.4272	0.7539	0.143*
H1C	−0.1225	0.4220	0.8864	0.143*
C2	0.1762 (4)	0.2088 (4)	0.3329 (3)	0.0765 (8)
H2A	0.2870	0.2400	0.3409	0.115*
H2B	0.1272	0.2484	0.2407	0.115*
H2C	0.1609	0.0962	0.3274	0.115*
C3	0.0551 (3)	0.2502 (3)	0.7257 (3)	0.0563 (6)
C4	0.0913 (3)	0.1979 (3)	0.8721 (3)	0.0629 (6)
H4	0.0267	0.2187	0.9518	0.075*
C5	0.2224 (3)	0.1151 (3)	0.9009 (3)	0.0614 (6)
H5	0.2446	0.0798	0.9998	0.074*
C6	0.3208 (3)	0.0839 (3)	0.7857 (2)	0.0536 (5)
C7	0.2846 (3)	0.1357 (3)	0.6355 (2)	0.0532 (5)
H7	0.3497	0.1150	0.5562	0.064*
C8	0.1542 (3)	0.2161 (3)	0.6063 (2)	0.0518 (5)
C9	0.4603 (3)	−0.0029 (3)	0.8201 (3)	0.0592 (6)
H9	0.4750	−0.0452	0.9168	0.071*
C10	0.8018 (3)	−0.1300 (3)	0.6745 (3)	0.0592 (6)
C11	1.0411 (4)	−0.2537 (4)	0.6641 (4)	0.0831 (8)
H11A	1.0612	−0.1752	0.5909	0.125*
H11B	1.0213	−0.3547	0.6096	0.125*
H11C	1.1313	−0.2552	0.7374	0.125*
C12	0.8912 (4)	0.8997 (4)	0.1431 (4)	0.0832 (9)
H12A	0.8874	0.9151	0.2538	0.125*
H12B	0.8869	0.9989	0.0963	0.125*
H12C	0.9876	0.8546	0.1209	0.125*
C13	0.4029 (4)	0.5264 (5)	−0.1260 (4)	0.1025 (12)
H13A	0.4310	0.4251	−0.1626	0.154*
H13B	0.3617	0.5814	−0.2124	0.154*
H13C	0.3243	0.5137	−0.0525	0.154*
C14	0.6174 (3)	0.5505 (3)	0.0681 (2)	0.0507 (5)
C15	0.7418 (3)	0.6523 (3)	0.1397 (2)	0.0537 (5)
C16	0.5874 (3)	0.4031 (3)	0.1205 (3)	0.0526 (5)
H16	0.5047	0.3365	0.0728	0.063*
C17	0.8352 (3)	0.6017 (3)	0.2610 (3)	0.0702 (7)
H17	0.9194	0.6672	0.3073	0.084*
C18	0.6816 (3)	0.3529 (3)	0.2460 (3)	0.0567 (6)
C19	0.8042 (3)	0.4530 (3)	0.3147 (3)	0.0718 (7)
H19	0.8669	0.4205	0.3980	0.086*
C20	0.6530 (3)	0.1995 (3)	0.3102 (3)	0.0615 (6)
H20	0.7189	0.1738	0.3944	0.074*
C21	0.4159 (3)	−0.1482 (3)	0.2941 (3)	0.0641 (6)
C22	0.3184 (5)	−0.3964 (4)	0.3679 (5)	0.1022 (11)
H22A	0.3118	−0.4332	0.2604	0.153*
H22B	0.2171	−0.3659	0.3945	0.153*
H22C	0.3501	−0.4787	0.4321	0.153*
O1	−0.0693 (2)	0.3330 (2)	0.6835 (2)	0.0744 (5)
O2	0.1079 (2)	0.2698 (2)	0.46445 (18)	0.0699 (5)
O3	0.8131 (2)	−0.0794 (2)	0.5477 (2)	0.0717 (5)
O4	0.9058 (2)	−0.2180 (3)	0.7456 (2)	0.0807 (6)
O5	0.7603 (2)	0.7965 (2)	0.08141 (19)	0.0666 (5)
O6	0.5370 (2)	0.6126 (2)	−0.0536 (2)	0.0718 (5)
O7	0.3145 (3)	−0.1471 (3)	0.1902 (3)	0.0887 (6)
O8	0.4310 (3)	−0.2649 (2)	0.3923 (3)	0.0874 (6)
N1	0.5617 (2)	−0.0216 (2)	0.7210 (2)	0.0583 (5)
N2	0.6856 (3)	−0.1066 (3)	0.7687 (2)	0.0703 (6)
H2	0.6889	−0.1449	0.8591	0.084*
N3	0.5424 (3)	0.0995 (2)	0.2565 (2)	0.0588 (5)
N4	0.5318 (3)	−0.0368 (3)	0.3347 (2)	0.0673 (6)
H4A	0.6002	−0.0504	0.4102	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.081 (2)	0.116 (3)	0.097 (2)	0.042 (2)	0.0291 (18)	0.017 (2)
C2	0.099 (2)	0.0901 (19)	0.0422 (12)	0.0300 (16)	−0.0048 (12)	0.0068 (12)
C3	0.0583 (14)	0.0597 (13)	0.0518 (12)	0.0102 (11)	0.0027 (10)	0.0076 (10)
C4	0.0675 (15)	0.0741 (15)	0.0496 (12)	0.0091 (13)	0.0129 (11)	0.0103 (11)
C5	0.0705 (15)	0.0721 (15)	0.0427 (11)	0.0089 (13)	0.0001 (11)	0.0165 (11)
C6	0.0577 (13)	0.0558 (12)	0.0471 (11)	0.0071 (11)	−0.0046 (10)	0.0112 (9)
C7	0.0587 (13)	0.0585 (13)	0.0436 (11)	0.0117 (11)	0.0016 (9)	0.0081 (9)
C8	0.0587 (13)	0.0552 (13)	0.0422 (10)	0.0105 (11)	−0.0015 (10)	0.0090 (9)
C9	0.0674 (15)	0.0662 (14)	0.0452 (11)	0.0133 (12)	−0.0054 (11)	0.0177 (10)
C10	0.0615 (14)	0.0592 (13)	0.0566 (13)	0.0099 (11)	−0.0093 (11)	0.0135 (10)
C11	0.0677 (17)	0.092 (2)	0.090 (2)	0.0219 (15)	−0.0067 (15)	0.0067 (16)
C12	0.091 (2)	0.0815 (19)	0.0730 (17)	−0.0176 (17)	−0.0081 (15)	0.0207 (14)
C13	0.089 (2)	0.105 (2)	0.106 (2)	−0.0075 (19)	−0.053 (2)	0.038 (2)
C14	0.0481 (12)	0.0640 (14)	0.0422 (11)	0.0168 (11)	−0.0008 (9)	0.0126 (10)
C15	0.0551 (13)	0.0624 (14)	0.0448 (11)	0.0102 (11)	0.0017 (10)	0.0110 (10)
C16	0.0486 (12)	0.0607 (13)	0.0496 (11)	0.0114 (10)	−0.0014 (9)	0.0102 (10)
C17	0.0685 (16)	0.0735 (17)	0.0653 (15)	0.0014 (13)	−0.0223 (13)	0.0166 (13)
C18	0.0585 (13)	0.0636 (14)	0.0504 (12)	0.0180 (11)	−0.0002 (10)	0.0132 (10)
C19	0.0718 (17)	0.0781 (18)	0.0643 (15)	0.0126 (14)	−0.0234 (13)	0.0233 (13)
C20	0.0662 (15)	0.0662 (15)	0.0537 (12)	0.0176 (13)	−0.0069 (11)	0.0184 (11)
C21	0.0727 (16)	0.0660 (16)	0.0561 (13)	0.0164 (14)	0.0075 (12)	0.0091 (11)
C22	0.111 (3)	0.071 (2)	0.128 (3)	−0.0024 (19)	0.041 (2)	0.0078 (19)
N1	0.0612 (12)	0.0607 (11)	0.0540 (11)	0.0133 (9)	−0.0076 (10)	0.0181 (8)
N2	0.0719 (13)	0.0897 (16)	0.0546 (11)	0.0293 (12)	−0.0013 (10)	0.0319 (10)
N3	0.0676 (13)	0.0635 (12)	0.0486 (10)	0.0196 (11)	0.0029 (9)	0.0168 (9)
N4	0.0769 (14)	0.0669 (13)	0.0583 (11)	0.0081 (11)	−0.0087 (10)	0.0205 (10)
O1	0.0711 (11)	0.0905 (13)	0.0677 (11)	0.0342 (10)	0.0122 (9)	0.0139 (10)
O2	0.0782 (11)	0.0920 (12)	0.0454 (8)	0.0393 (10)	0.0027 (8)	0.0183 (8)
O3	0.0715 (12)	0.0859 (12)	0.0610 (10)	0.0180 (10)	0.0011 (8)	0.0244 (9)
O4	0.0763 (13)	0.0995 (14)	0.0718 (12)	0.0382 (11)	0.0003 (10)	0.0232 (10)
O5	0.0733 (11)	0.0656 (11)	0.0592 (9)	−0.0022 (9)	−0.0081 (8)	0.0193 (8)
O6	0.0687 (11)	0.0774 (12)	0.0671 (10)	0.0021 (9)	−0.0223 (9)	0.0287 (9)
O7	0.0872 (14)	0.0865 (14)	0.0891 (14)	0.0035 (11)	−0.0180 (12)	0.0127 (11)
O8	0.1069 (16)	0.0683 (12)	0.0869 (13)	0.0002 (11)	0.0003 (12)	0.0223 (10)

Geometric parameters (Å, º) top

C1—O1	1.429 (3)	C12—H12B	0.9600
C1—H1A	0.9600	C12—H12C	0.9600
C1—H1B	0.9600	C13—O6	1.402 (4)
C1—H1C	0.9600	C13—H13A	0.9600
C2—O2	1.407 (3)	C13—H13B	0.9600
C2—H2A	0.9600	C13—H13C	0.9600
C2—H2B	0.9600	C14—O6	1.363 (3)
C2—H2C	0.9600	C15—O5	1.359 (3)
C3—O1	1.355 (3)	C15—C17	1.375 (3)
C3—C4	1.382 (3)	C15—C14	1.407 (3)
C4—H4	0.9300	C16—C14	1.374 (3)
C5—C4	1.381 (4)	C16—H16	0.9300
C5—H5	0.9300	C17—H17	0.9300
C6—C5	1.375 (3)	C18—C19	1.380 (4)
C6—C7	1.411 (3)	C18—C16	1.404 (3)
C6—C9	1.467 (3)	C18—C20	1.461 (3)
C7—H7	0.9300	C19—C17	1.389 (4)
C8—C7	1.363 (3)	C19—H19	0.9300
C8—O2	1.369 (3)	C20—N3	1.271 (3)
C8—C3	1.412 (3)	C20—H20	0.9300
C9—N1	1.272 (3)	C21—O7	1.200 (3)
C9—H9	0.9300	C21—N4	1.336 (4)
C10—O3	1.204 (3)	C21—O8	1.349 (3)
C10—O4	1.339 (3)	C22—O8	1.422 (4)
C10—N2	1.347 (3)	C22—H22A	0.9600
C11—O4	1.438 (4)	C22—H22B	0.9600
C11—H11A	0.9600	C22—H22C	0.9600
C11—H11B	0.9600	N1—N2	1.375 (3)
C11—H11C	0.9600	N2—H2	0.8600
C12—O5	1.425 (3)	N3—N4	1.377 (3)
C12—H12A	0.9600	N4—H4A	0.8600

O1—C1—H1A	109.5	O6—C13—H13B	109.5
O1—C1—H1B	109.5	H13A—C13—H13B	109.5
H1A—C1—H1B	109.5	O6—C13—H13C	109.5
O1—C1—H1C	109.5	H13A—C13—H13C	109.5
H1A—C1—H1C	109.5	H13B—C13—H13C	109.5
H1B—C1—H1C	109.5	O6—C14—C16	125.9 (2)
O2—C2—H2A	109.5	O6—C14—C15	113.64 (19)
O2—C2—H2B	109.5	C16—C14—C15	120.47 (19)
H2A—C2—H2B	109.5	O5—C15—C17	124.6 (2)
O2—C2—H2C	109.5	O5—C15—C14	116.08 (18)
H2A—C2—H2C	109.5	C17—C15—C14	119.4 (2)
H2B—C2—H2C	109.5	C14—C16—C18	119.9 (2)
O1—C3—C4	126.0 (2)	C14—C16—H16	120.0
O1—C3—C8	115.39 (19)	C18—C16—H16	120.0
C4—C3—C8	118.6 (2)	C15—C17—C19	120.2 (2)
C5—C4—C3	120.5 (2)	C15—C17—H17	119.9
C5—C4—H4	119.7	C19—C17—H17	119.9
C3—C4—H4	119.7	C19—C18—C16	119.2 (2)
C6—C5—C4	121.0 (2)	C19—C18—C20	118.1 (2)
C6—C5—H5	119.5	C16—C18—C20	122.6 (2)
C4—C5—H5	119.5	C18—C19—C17	120.9 (2)
C5—C6—C7	119.0 (2)	C18—C19—H19	119.6
C5—C6—C9	119.85 (19)	C17—C19—H19	119.6
C7—C6—C9	121.2 (2)	N3—C20—C18	123.1 (2)
C8—C7—C6	120.1 (2)	N3—C20—H20	118.5
C8—C7—H7	119.9	C18—C20—H20	118.5
C6—C7—H7	119.9	O7—C21—N4	127.2 (3)
C7—C8—O2	124.6 (2)	O7—C21—O8	124.9 (3)
C7—C8—C3	120.68 (19)	N4—C21—O8	107.8 (2)
O2—C8—C3	114.69 (19)	O8—C22—H22A	109.5
N1—C9—C6	121.68 (18)	O8—C22—H22B	109.5
N1—C9—H9	119.2	H22A—C22—H22B	109.5
C6—C9—H9	119.2	O8—C22—H22C	109.5
O3—C10—O4	124.9 (2)	H22A—C22—H22C	109.5
O3—C10—N2	126.3 (2)	H22B—C22—H22C	109.5
O4—C10—N2	108.8 (2)	C9—N1—N2	115.30 (18)
O4—C11—H11A	109.5	C10—N2—N1	120.23 (19)
O4—C11—H11B	109.5	C10—N2—H2	119.9
H11A—C11—H11B	109.5	N1—N2—H2	119.9
O4—C11—H11C	109.5	C20—N3—N4	114.63 (19)
H11A—C11—H11C	109.5	C21—N4—N3	120.4 (2)
H11B—C11—H11C	109.5	C21—N4—H4A	119.8
O5—C12—H12A	109.5	N3—N4—H4A	119.8
O5—C12—H12B	109.5	C3—O1—C1	118.0 (2)
H12A—C12—H12B	109.5	C8—O2—C2	117.77 (18)
O5—C12—H12C	109.5	C10—O4—C11	117.2 (2)
H12A—C12—H12C	109.5	C15—O5—C12	118.1 (2)
H12B—C12—H12C	109.5	C14—O6—C13	118.5 (2)
O6—C13—H13A	109.5	C21—O8—C22	116.6 (3)

O2—C8—C3—O1	−1.1 (3)	C17—C15—C14—C16	1.2 (3)
C7—C8—C3—C4	−1.2 (3)	C18—C16—C14—O6	178.9 (2)
O2—C8—C3—C4	178.8 (2)	C18—C16—C14—C15	−0.2 (3)
C7—C8—C3—O1	178.9 (2)	O5—C15—C14—O6	1.9 (3)
C8—C3—C4—C5	0.5 (4)	C17—C15—C14—O6	−178.0 (2)
C6—C5—C4—C3	0.6 (4)	O5—C15—C14—C16	−178.9 (2)
O1—C3—C4—C5	−179.6 (2)	C19—C18—C16—C14	−0.3 (3)
C7—C6—C5—C4	−1.0 (4)	C20—C18—C16—C14	178.1 (2)
C9—C6—C5—C4	179.3 (2)	O5—C15—C17—C19	178.4 (3)
O2—C8—C7—C6	−179.2 (2)	C14—C15—C17—C19	−1.6 (4)
C3—C8—C7—C6	0.8 (3)	C18—C19—C17—C15	1.1 (4)
C5—C6—C7—C8	0.3 (3)	C16—C18—C19—C17	−0.1 (4)
C9—C6—C7—C8	180.0 (2)	C20—C18—C19—C17	−178.6 (3)
C5—C6—C9—N1	−173.5 (2)	C19—C18—C20—N3	179.3 (2)
C7—C6—C9—N1	6.8 (4)	C16—C18—C20—N3	0.8 (4)
C6—C9—N1—N2	−179.4 (2)	C18—C20—N3—N4	−178.5 (2)
O3—C10—N2—N1	2.1 (4)	O7—C21—N4—N3	1.5 (4)
O4—C10—N2—N1	−178.7 (2)	O8—C21—N4—N3	−178.0 (2)
C9—N1—N2—C10	−178.3 (2)	C20—N3—N4—C21	176.9 (2)
C4—C3—O1—C1	−2.6 (4)	C17—C15—O5—C12	4.1 (4)
C8—C3—O1—C1	177.3 (3)	C14—C15—O5—C12	−175.8 (2)
C7—C8—O2—C2	15.2 (4)	C16—C14—O6—C13	5.7 (4)
C3—C8—O2—C2	−164.8 (2)	C15—C14—O6—C13	−175.1 (3)
O3—C10—O4—C11	0.3 (4)	O7—C21—O8—C22	0.8 (4)
N2—C10—O4—C11	−178.9 (2)	N4—C21—O8—C22	−179.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5ⁱ	0.86	2.07	2.902 (3)	164
N2—H2···O6ⁱ	0.86	2.54	3.153 (3)	129
N4—H4A···O3	0.86	2.13	2.968 (3)	164
C11—H11A···O3	0.96	2.33	2.701 (4)	102
C19—H19···O2ⁱⁱ	0.93	2.55	3.337 (3)	143
C13—H13A···Cg1ⁱⁱⁱ	0.96	2.94	3.531 (4)	121

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₄N₂O₄
M_r	238.24
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	8.5276 (11), 8.5517 (11), 8.6259 (11)
α, β, γ (°)	92.919 (5), 94.209 (4), 94.146 (5)
V (Å³)	624.71 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.23 × 0.21 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.971, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	3471, 2172, 1985
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.080, 1.04
No. of reflections	2172
No. of parameters	314
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.10

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···O5ⁱ	0.86	2.07	2.902 (3)	163.5
N2—H2···O6ⁱ	0.86	2.54	3.153 (3)	128.9
N4—H4A···O3	0.86	2.13	2.968 (3)	164.2
C11—H11A···O3	0.96	2.33	2.701 (4)	101.9
C19—H19···O2ⁱⁱ	0.93	2.55	3.337 (3)	142.6
C13—H13A···Cg1ⁱⁱⁱ	0.96	2.94	3.531 (4)	121.00

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

Acknowledgements

The authors thank Hangzhou Vocational and Technical College, China, for financial support.

References

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