N′-(3,4-Dimethoxy­benzyl­idene)aceto­hydrazide

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

doi:10.1107/S1600536809028608

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1964

doi:10.1107/S1600536809028608

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N′-(3,4-Dimethoxybenzylidene)acetohydrazide

Bao-Cheng Zhou,^a,^b ^* Lu-Ping Lv,^c Wen-Bo Yu,^c Wei-Wei Li ^c and Xian-Chao Hu ^d

^aDepartment of Applied Chemistry, Zhejiang Sci-tech University, Hangzhou 310018, People's Republic of China, ^bKey Laboratory of Advanced Textile Materials and Manufacturing Technology, Ministry of Education, Zhejiang Sci-Tech University, Hangzhou 310018, People's Republic of China, ^cDepartment of Chemical Engineering, Hangzhou Vocational and Technical College, Hangzhou 310018, People's Republic of China, and ^dResearch Center of Analysis and Measurement, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: zjlgzbc@126.com

(Received 7 July 2009; accepted 20 July 2009; online 25 July 2009)

The asymmetric unit of the title compound, C₁₁H₁₄N₂O₃, contains two independent molecules with close conformations; the C=N—N—C torsion angle is 176.4 (1)° in both molecules. In the crystal, intermolecular N—H⋯O and C—H⋯O hydrogen bonds link the molecules into chains running along the [01 $[\overline{1}]$ ] direction.

Related literature

For general background to the applications of Schiff bases, see: Cimerman et al. (1997 ); Offe et al. (1952 ); Richardson et al. (1988 ). For related structures, see: Li & Jian (2008 ); Tamboura et al. (2009 ).

Experimental

Crystal data

C₁₁H₁₄N₂O₃
M_r = 222.24
Triclinic, P 1
a = 8.339 (3) Å
b = 8.349 (3) Å
c = 8.663 (3) Å
α = 94.717 (12)°
β = 95.210 (8)°
γ = 94.298 (12)°
V = 596.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 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 = 0.987, T_max = 0.990
3236 measured reflections
2054 independent reflections
1890 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.110
S = 1.12
2054 reflections
290 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4ⁱ	0.86	2.11	2.950 (3)	165
N2—H2⋯O5ⁱ	0.86	2.54	3.154 (3)	129
C7—H7⋯O6	0.93	2.52	3.372 (3)	152
C12—H12B⋯O3ⁱⁱ	0.96	2.51	3.434 (4)	162
C12—H12C⋯O6ⁱⁱⁱ	0.96	2.45	3.367 (4)	159
C16—H18⋯O2^iv	0.93	2.45	3.244 (3)	144
N4—H4⋯O3^v	0.86	2.08	2.907 (3)	161
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z-1; (iii) x-1, y-1, z; (iv) x-1, y, z-1; (v) x, y, z-1.

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/S1600536809028608/cv2586sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028608/cv2586Isup2.hkl

checkCIF report

Comment top

Schiff bases have attracted much attention due to their possible analytical applications (Cimerman et al., 1997). They are also important ligands, which have been reported to have mild bacteriostatic activity and potential oral iron-chelating drugs for genetic disorders such as thalassemia (Offe et al., 1952; Richardson et al., 1988). Metal complexes based on Schiff bases have received considerable attention because they can be utilized as model compounds of active centres in various complexes (Tamboura et al., 2009). We report here the crystal structure of the title compound.

The title compound (Fig. 1) crystallizes with two independent molecules in the asymmetric unit. The side chains in the two independent molecules have the same orientations, with the C═N—N—C torsion angle being 176.4 (1)° in both molecules. The N1/N2//O3/C9/C10/C11 and N3/N4/O6/C20/C21/C22 planes form dihedral angles of 6.00 (5)° and 4.38 (9)°, respectively, with the C2—C7 and C13—C18 planes. The dihedral angle between the two independent benzene rings is 79.39 (7)°. The bond lengths and angles are comparable to those observed for N'-[1-(4-methoxyphenyl)ethylidene]acetohydrazide (Li et al., 2008).

In the crystal structure, the molecules are linked into chains running along the [01-1] by N—H···O and C—H···O hydrogen bonds(Table 1).

Related literature top

For general background to the applications of Schiff bases, see: Cimerman et al. (1997); Offe et al. (1952); Richardson et al. (1988). For related structures, see: Li et al. (2008); Tamboura et al. (2009).

Experimental top

3,4-Methoxybenzaldehyde (1.66 g, 0.01 mol) and acetohydrazide (0.74 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 85% yield. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an 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. The content of asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level.

N'-(3,4-Dimethoxybenzylidene)acetohydrazide top

Crystal data top

C₁₁H₁₄N₂O₃	Z = 2
M_r = 222.24	F(000) = 236
Triclinic, P1	D_x = 1.237 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.339 (3) Å	Cell parameters from 2054 reflections
b = 8.349 (3) Å	θ = 2.4–25.0°
c = 8.663 (3) Å	µ = 0.09 mm⁻¹
α = 94.717 (12)°	T = 223 K
β = 95.210 (8)°	Block, colourless
γ = 94.298 (12)°	0.24 × 0.21 × 0.19 mm
V = 596.6 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2054 independent reflections
Radiation source: fine-focus sealed tube	1890 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→9
T_min = 0.987, T_max = 0.990	k = −9→9
3236 measured reflections	l = −10→9

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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.0737P)² + 0.0315P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
2054 reflections	Δρ_max = 0.18 e Å⁻³
290 parameters	Δρ_min = −0.15 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: 0.101 (14)

Crystal data top

C₁₁H₁₄N₂O₃	γ = 94.298 (12)°
M_r = 222.24	V = 596.6 (3) Å³
Triclinic, P1	Z = 2
a = 8.339 (3) Å	Mo Kα radiation
b = 8.349 (3) Å	µ = 0.09 mm⁻¹
c = 8.663 (3) Å	T = 223 K
α = 94.717 (12)°	0.24 × 0.21 × 0.19 mm
β = 95.210 (8)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2054 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1890 reflections with I > 2σ(I)
T_min = 0.987, T_max = 0.990	R_int = 0.017
3236 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	3 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.12	Δρ_max = 0.18 e Å⁻³
2054 reflections	Δρ_min = −0.15 e Å⁻³
290 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
O4	0.0007 (2)	−0.4436 (3)	0.6700 (2)	0.0538 (6)
O5	0.2416 (3)	−0.2594 (3)	0.8028 (3)	0.0604 (6)
O2	0.6714 (3)	0.0884 (3)	1.2796 (3)	0.0691 (7)
O3	−0.0291 (3)	0.4482 (3)	1.2193 (3)	0.0668 (7)
N2	0.0775 (3)	0.4780 (3)	0.9931 (3)	0.0520 (6)
H2	0.0686	0.5156	0.9036	0.062*
O1	0.8549 (3)	0.0361 (3)	1.0637 (3)	0.0659 (7)
N3	0.2418 (3)	0.2632 (3)	0.5009 (3)	0.0473 (6)
N1	0.2086 (3)	0.3943 (3)	1.0364 (3)	0.0476 (6)
C15	0.1580 (3)	−0.1968 (3)	0.6814 (3)	0.0428 (6)
O6	0.4783 (3)	0.5122 (3)	0.5771 (3)	0.0796 (8)
C18	0.1933 (3)	−0.0476 (4)	0.6295 (3)	0.0449 (6)
H17	0.2816	0.0189	0.6767	0.054*
C6	0.4492 (3)	0.2834 (3)	0.9661 (3)	0.0460 (7)
N4	0.2566 (3)	0.4016 (3)	0.4235 (3)	0.0508 (6)
H4	0.1872	0.4136	0.3465	0.061*
C17	0.0956 (3)	0.0041 (4)	0.5047 (3)	0.0456 (7)
C2	0.7255 (3)	0.1177 (4)	1.0226 (3)	0.0479 (7)
C9	0.3061 (4)	0.3708 (4)	0.9334 (3)	0.0474 (7)
H9	0.2861	0.4097	0.8365	0.057*
C5	0.4882 (3)	0.2291 (4)	1.1140 (3)	0.0476 (7)
H6	0.4221	0.2488	1.1932	0.057*
C20	0.1279 (4)	0.1605 (4)	0.4428 (3)	0.0497 (7)
H20	0.0619	0.1854	0.3571	0.060*
C10	−0.0362 (4)	0.5003 (3)	1.0920 (3)	0.0484 (7)
C14	−0.0720 (4)	−0.2478 (4)	0.4888 (4)	0.0535 (7)
H14	−0.1612	−0.3137	0.4425	0.064*
C13	0.0239 (3)	−0.2980 (3)	0.6102 (3)	0.0446 (7)
C7	0.5492 (4)	0.2542 (4)	0.8501 (3)	0.0508 (7)
H7	0.5252	0.2903	0.7526	0.061*
C16	−0.0345 (4)	−0.0966 (4)	0.4350 (4)	0.0556 (8)
H18	−0.0980	−0.0638	0.3515	0.067*
C11	−0.1735 (4)	0.5935 (5)	1.0337 (4)	0.0623 (8)
H11A	−0.1585	0.6212	0.9303	0.093*
H11B	−0.1758	0.6903	1.1012	0.093*
H11C	−0.2737	0.5286	1.0324	0.093*
C4	0.6230 (4)	0.1474 (4)	1.1414 (3)	0.0495 (7)
C3	0.6859 (4)	0.1710 (4)	0.8788 (4)	0.0548 (8)
H3	0.7517	0.1510	0.7994	0.066*
C21	0.3770 (4)	0.5174 (4)	0.4662 (3)	0.0524 (7)
C12	−0.1272 (4)	−0.5549 (5)	0.5953 (4)	0.0641 (9)
H12A	−0.1310	−0.6517	0.6478	0.096*
H12B	−0.1082	−0.5803	0.4887	0.096*
H12C	−0.2282	−0.5072	0.5992	0.096*
C22	0.3783 (5)	0.6553 (4)	0.3640 (5)	0.0694 (9)
H22A	0.2882	0.6378	0.2856	0.104*
H22B	0.4771	0.6615	0.3151	0.104*
H22C	0.3704	0.7545	0.4263	0.104*
C8	0.5745 (5)	0.1116 (5)	1.4029 (4)	0.0672 (9)
H5A	0.6225	0.0673	1.4932	0.101*
H5B	0.4687	0.0584	1.3734	0.101*
H5C	0.5660	0.2248	1.4263	0.101*
C1	0.9669 (5)	0.0112 (5)	0.9511 (5)	0.0775 (11)
H1A	1.0525	−0.0478	0.9934	0.116*
H1B	1.0112	0.1136	0.9244	0.116*
H1C	0.9125	−0.0489	0.8596	0.116*
C19	0.3937 (5)	−0.1813 (5)	0.8631 (5)	0.0800 (12)
H16A	0.4381	−0.2371	0.9475	0.120*
H16B	0.3805	−0.0720	0.9001	0.120*
H16C	0.4656	−0.1820	0.7826	0.120*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0553 (11)	0.0539 (13)	0.0528 (12)	−0.0019 (9)	−0.0015 (9)	0.0211 (10)
O5	0.0625 (12)	0.0572 (13)	0.0598 (12)	−0.0038 (10)	−0.0176 (10)	0.0294 (10)
O2	0.0710 (15)	0.1024 (19)	0.0436 (11)	0.0453 (14)	0.0073 (10)	0.0281 (12)
O3	0.0708 (15)	0.0814 (16)	0.0526 (13)	0.0172 (12)	0.0043 (11)	0.0239 (12)
N2	0.0547 (13)	0.0591 (15)	0.0458 (14)	0.0141 (11)	−0.0031 (12)	0.0261 (12)
O1	0.0580 (13)	0.0810 (16)	0.0649 (15)	0.0280 (12)	0.0127 (11)	0.0158 (12)
N3	0.0566 (14)	0.0477 (14)	0.0414 (13)	0.0132 (11)	0.0059 (11)	0.0173 (11)
N1	0.0507 (13)	0.0483 (14)	0.0447 (13)	0.0096 (10)	−0.0062 (11)	0.0161 (10)
C15	0.0420 (14)	0.0495 (16)	0.0393 (14)	0.0100 (12)	0.0007 (11)	0.0161 (12)
O6	0.0796 (17)	0.0751 (17)	0.0801 (18)	0.0006 (13)	−0.0203 (14)	0.0187 (14)
C18	0.0451 (14)	0.0492 (16)	0.0418 (14)	0.0081 (12)	0.0012 (11)	0.0125 (12)
C6	0.0512 (15)	0.0472 (16)	0.0384 (14)	0.0000 (12)	−0.0047 (12)	0.0102 (12)
N4	0.0613 (14)	0.0500 (14)	0.0431 (13)	0.0082 (11)	−0.0015 (11)	0.0199 (11)
C17	0.0505 (16)	0.0472 (16)	0.0422 (15)	0.0143 (12)	0.0045 (12)	0.0128 (12)
C2	0.0483 (16)	0.0502 (17)	0.0464 (16)	0.0092 (13)	0.0046 (13)	0.0073 (13)
C9	0.0559 (16)	0.0490 (16)	0.0377 (14)	0.0054 (12)	−0.0041 (12)	0.0151 (12)
C5	0.0508 (16)	0.0535 (17)	0.0398 (14)	0.0120 (13)	0.0009 (12)	0.0089 (12)
C20	0.0583 (17)	0.0485 (17)	0.0444 (15)	0.0142 (13)	−0.0010 (13)	0.0150 (13)
C10	0.0560 (17)	0.0440 (16)	0.0443 (16)	0.0034 (12)	−0.0055 (14)	0.0100 (12)
C14	0.0471 (15)	0.0567 (18)	0.0551 (18)	0.0026 (13)	−0.0091 (13)	0.0126 (14)
C13	0.0463 (15)	0.0473 (16)	0.0425 (15)	0.0068 (12)	0.0039 (12)	0.0154 (12)
C7	0.0595 (18)	0.0554 (17)	0.0379 (14)	0.0002 (14)	0.0021 (13)	0.0138 (13)
C16	0.0579 (17)	0.0571 (19)	0.0532 (18)	0.0137 (14)	−0.0092 (14)	0.0207 (15)
C11	0.063 (2)	0.063 (2)	0.0614 (19)	0.0159 (16)	0.0004 (16)	0.0106 (16)
C4	0.0532 (16)	0.0593 (18)	0.0381 (15)	0.0133 (14)	−0.0005 (12)	0.0137 (13)
C3	0.0588 (17)	0.0587 (18)	0.0487 (17)	0.0019 (14)	0.0106 (14)	0.0117 (14)
C21	0.0583 (18)	0.0516 (18)	0.0488 (17)	0.0116 (14)	0.0021 (14)	0.0097 (13)
C12	0.066 (2)	0.065 (2)	0.060 (2)	−0.0107 (16)	0.0014 (16)	0.0203 (16)
C22	0.085 (2)	0.0533 (19)	0.071 (2)	0.0030 (17)	0.0061 (19)	0.0154 (17)
C8	0.081 (2)	0.087 (2)	0.0413 (17)	0.0353 (19)	0.0107 (16)	0.0201 (16)
C1	0.063 (2)	0.078 (3)	0.099 (3)	0.0206 (18)	0.031 (2)	0.010 (2)
C19	0.073 (2)	0.073 (2)	0.088 (3)	−0.0081 (18)	−0.037 (2)	0.033 (2)

Geometric parameters (Å, º) top

O4—C13	1.367 (3)	C5—H6	0.9300
O4—C12	1.431 (4)	C20—H20	0.9300
O5—C15	1.370 (3)	C10—C11	1.505 (4)
O5—C19	1.417 (4)	C14—C13	1.376 (4)
O2—C4	1.370 (3)	C14—C16	1.405 (4)
O2—C8	1.407 (4)	C14—H14	0.9300
O3—C10	1.216 (4)	C7—C3	1.393 (5)
N2—C10	1.348 (4)	C7—H7	0.9300
N2—N1	1.380 (3)	C16—H18	0.9300
N2—H2	0.8600	C11—H11A	0.9600
O1—C2	1.355 (4)	C11—H11B	0.9600
O1—C1	1.424 (5)	C11—H11C	0.9600
N3—C20	1.270 (4)	C3—H3	0.9300
N3—N4	1.385 (3)	C21—O6	1.225 (4)
N1—C9	1.274 (4)	C21—C22	1.510 (5)
C15—C18	1.379 (4)	C12—H12A	0.9600
C15—C13	1.412 (4)	C12—H12B	0.9600
O6—C21	1.225 (4)	C12—H12C	0.9600
C18—C17	1.410 (4)	C22—H22A	0.9600
C18—H17	0.9300	C22—H22B	0.9600
C6—C7	1.381 (4)	C22—H22C	0.9600
C6—C5	1.413 (4)	C8—H5A	0.9600
C6—C9	1.463 (4)	C8—H5B	0.9600
N4—C21	1.345 (4)	C8—H5C	0.9600
N4—H4	0.8600	C1—H1A	0.9600
C17—C16	1.381 (4)	C1—H1B	0.9600
C17—C20	1.468 (4)	C1—H1C	0.9600
C2—C3	1.377 (4)	C19—H16A	0.9600
C2—C4	1.415 (4)	C19—H16B	0.9600
C9—H9	0.9300	C19—H16C	0.9600
C5—C4	1.370 (4)

C13—O4—C12	117.5 (2)	C17—C16—H18	119.6
C15—O5—C19	118.3 (2)	C14—C16—H18	119.6
C4—O2—C8	117.6 (2)	C10—C11—H11A	109.5
C10—N2—N1	119.6 (2)	C10—C11—H11B	109.5
C10—N2—H2	120.2	H11A—C11—H11B	109.5
N1—N2—H2	120.2	C10—C11—H11C	109.5
C2—O1—C1	117.2 (3)	H11A—C11—H11C	109.5
C20—N3—N4	114.6 (2)	H11B—C11—H11C	109.5
C9—N1—N2	115.8 (2)	C5—C4—O2	125.2 (3)
O5—C15—C18	125.6 (3)	C5—C4—C2	120.5 (2)
O5—C15—C13	114.2 (2)	O2—C4—C2	114.3 (2)
C18—C15—C13	120.2 (2)	C2—C3—C7	121.2 (3)
C15—C18—C17	120.0 (3)	C2—C3—H3	119.4
C15—C18—H17	120.0	C7—C3—H3	119.4
C17—C18—H17	120.0	O6—C21—N4	123.7 (3)
C7—C6—C5	119.2 (3)	O6—C21—N4	123.7 (3)
C7—C6—C9	119.3 (2)	O6—C21—C22	122.4 (3)
C5—C6—C9	121.5 (3)	O6—C21—C22	122.4 (3)
C21—N4—N3	121.4 (2)	N4—C21—C22	114.0 (3)
C21—N4—H4	119.3	O4—C12—H12A	109.5
N3—N4—H4	119.3	O4—C12—H12B	109.5
C16—C17—C18	119.3 (2)	H12A—C12—H12B	109.5
C16—C17—C20	118.0 (2)	O4—C12—H12C	109.5
C18—C17—C20	122.7 (3)	H12A—C12—H12C	109.5
O1—C2—C3	126.3 (3)	H12B—C12—H12C	109.5
O1—C2—C4	115.0 (2)	C21—C22—H22A	109.5
C3—C2—C4	118.6 (3)	C21—C22—H22B	109.5
N1—C9—C6	120.6 (2)	H22A—C22—H22B	109.5
N1—C9—H9	119.7	C21—C22—H22C	109.5
C6—C9—H9	119.7	H22A—C22—H22C	109.5
C4—C5—C6	120.3 (3)	H22B—C22—H22C	109.5
C4—C5—H6	119.8	O2—C8—H5A	109.5
C6—C5—H6	119.8	O2—C8—H5B	109.5
N3—C20—C17	122.9 (3)	H5A—C8—H5B	109.5
N3—C20—H20	118.5	O2—C8—H5C	109.5
C17—C20—H20	118.5	H5A—C8—H5C	109.5
O3—C10—N2	122.5 (3)	H5B—C8—H5C	109.5
O3—C10—C11	122.2 (3)	O1—C1—H1A	109.5
N2—C10—C11	115.3 (3)	O1—C1—H1B	109.5
C13—C14—C16	119.6 (3)	H1A—C1—H1B	109.5
C13—C14—H14	120.2	O1—C1—H1C	109.5
C16—C14—H14	120.2	H1A—C1—H1C	109.5
O4—C13—C14	124.7 (2)	H1B—C1—H1C	109.5
O4—C13—C15	115.3 (2)	O5—C19—H16A	109.5
C14—C13—C15	120.0 (2)	O5—C19—H16B	109.5
C6—C7—C3	120.2 (3)	H16A—C19—H16B	109.5
C6—C7—H7	119.9	O5—C19—H16C	109.5
C3—C7—H7	119.9	H16A—C19—H16C	109.5
C17—C16—C14	120.9 (2)	H16B—C19—H16C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4ⁱ	0.86	2.11	2.950 (3)	165
N2—H2···O5ⁱ	0.86	2.54	3.154 (3)	129
C7—H7···O6	0.93	2.52	3.372 (3)	152
C12—H12B···O3ⁱⁱ	0.96	2.51	3.434 (4)	162
C12—H12C···O6ⁱⁱⁱ	0.96	2.45	3.367 (4)	159
C16—H18···O2^iv	0.93	2.45	3.244 (3)	144
N4—H4···O3^v	0.86	2.08	2.907 (3)	161

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₄N₂O₃
M_r	222.24
Crystal system, space group	Triclinic, P1
Temperature (K)	223
a, b, c (Å)	8.339 (3), 8.349 (3), 8.663 (3)
α, β, γ (°)	94.717 (12), 95.210 (8), 94.298 (12)
V (Å³)	596.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
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	0.987, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	3236, 2054, 1890
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.110, 1.12
No. of reflections	2054
No. of parameters	290
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.15

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···O4ⁱ	0.86	2.11	2.950 (3)	164.9
N2—H2···O5ⁱ	0.86	2.54	3.154 (3)	129.0
C7—H7···O6	0.93	2.52	3.372 (3)	151.8
C12—H12B···O3ⁱⁱ	0.96	2.51	3.434 (4)	161.5
C12—H12C···O6ⁱⁱⁱ	0.96	2.45	3.367 (4)	158.8
C16—H18···O2^iv	0.93	2.45	3.244 (3)	143.8
N4—H4···O3^v	0.86	2.08	2.907 (3)	161.3

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

Acknowledgements

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

References

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