organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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[Parashar, R. K., Sharma, R. C., Kumar, A. & Mohanm, G. (1988). Inorg. Chim Acta, 151, 201-208.]); Hadjoudis et al. (1987[Hadjoudis, E., Vittorakis, M. & Moustakali-Mavridis, J. (1987). Tetrahedron, 43, 1345-1360.]); Borg et al. (1999[Borg, S., Vollinga, R. C., Labarre, M., Payza, K., Terenius, L. & Luthman, K. (1999). J. Med. Chem. 42, 4331-4342.]). For a related structure, see: Shang et al. (2007[Shang, Z.-H., Zhang, H.-L. & Ding, Y. (2007). Acta Cryst. E63, o3394.]).

[Scheme 1]

Experimental

Crystal data
  • C11H14N2O4

  • Mr = 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[Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.971, Tmax = 0.979

  • 3471 measured reflections

  • 2172 independent reflections

  • 1985 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.11 e Å−3

  • Δρmin = −0.10 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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—H13ACg1iii 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[Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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 CN 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).

Refinement top

H atoms were included in the riding model approximation with N-H = 0.86Å. C-bound H atoms were positioned geometrically (C-H = 0.93Å and 0.96Å) and refined using a riding model, with Uiso(H) = 1.2-1.5Ueq(C). In the absence of significant anomalous dispersion effects, Friedel pairs were averaged.

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
[Figure 1] Fig. 1. Molecular structure of (I), showing 20% probability displacement ellipsoids and the atomic numbering.
[Figure 2] 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
C11H14N2O4Z = 2
Mr = 238.24F(000) = 252
Triclinic, P1Dx = 1.267 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.5276 (11) ÅCell parameters from 2172 reflections
b = 8.5517 (11) Åθ = 2.4–25.0°
c = 8.6259 (11) ŵ = 0.10 mm1
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 tube1985 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
ϕ and ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 910
Tmin = 0.971, Tmax = 0.979k = 109
3471 measured reflectionsl = 1010
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.080 w = 1/[σ2(Fo2) + (0.049P)2 + 0.0326P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.010
2172 reflectionsΔρmax = 0.11 e Å3
314 parametersΔρmin = 0.10 e Å3
3 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.034 (6)
Crystal data top
C11H14N2O4γ = 94.146 (5)°
Mr = 238.24V = 624.71 (14) Å3
Triclinic, P1Z = 2
a = 8.5276 (11) ÅMo Kα radiation
b = 8.5517 (11) ŵ = 0.10 mm1
c = 8.6259 (11) ÅT = 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)
Tmin = 0.971, Tmax = 0.979Rint = 0.013
3471 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0283 restraints
wR(F2) = 0.080H-atom parameters constrained
S = 1.04Δρmax = 0.11 e Å3
2172 reflectionsΔρmin = 0.10 e Å3
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
xyzUiso*/Ueq
C10.1778 (4)0.3653 (5)0.7975 (4)0.0950 (11)
H1A0.22610.26820.82890.143*
H1B0.25770.42720.75390.143*
H1C0.12250.42200.88640.143*
C20.1762 (4)0.2088 (4)0.3329 (3)0.0765 (8)
H2A0.28700.24000.34090.115*
H2B0.12720.24840.24070.115*
H2C0.16090.09620.32740.115*
C30.0551 (3)0.2502 (3)0.7257 (3)0.0563 (6)
C40.0913 (3)0.1979 (3)0.8721 (3)0.0629 (6)
H40.02670.21870.95180.075*
C50.2224 (3)0.1151 (3)0.9009 (3)0.0614 (6)
H50.24460.07980.99980.074*
C60.3208 (3)0.0839 (3)0.7857 (2)0.0536 (5)
C70.2846 (3)0.1357 (3)0.6355 (2)0.0532 (5)
H70.34970.11500.55620.064*
C80.1542 (3)0.2161 (3)0.6063 (2)0.0518 (5)
C90.4603 (3)0.0029 (3)0.8201 (3)0.0592 (6)
H90.47500.04520.91680.071*
C100.8018 (3)0.1300 (3)0.6745 (3)0.0592 (6)
C111.0411 (4)0.2537 (4)0.6641 (4)0.0831 (8)
H11A1.06120.17520.59090.125*
H11B1.02130.35470.60960.125*
H11C1.13130.25520.73740.125*
C120.8912 (4)0.8997 (4)0.1431 (4)0.0832 (9)
H12A0.88740.91510.25380.125*
H12B0.88690.99890.09630.125*
H12C0.98760.85460.12090.125*
C130.4029 (4)0.5264 (5)0.1260 (4)0.1025 (12)
H13A0.43100.42510.16260.154*
H13B0.36170.58140.21240.154*
H13C0.32430.51370.05250.154*
C140.6174 (3)0.5505 (3)0.0681 (2)0.0507 (5)
C150.7418 (3)0.6523 (3)0.1397 (2)0.0537 (5)
C160.5874 (3)0.4031 (3)0.1205 (3)0.0526 (5)
H160.50470.33650.07280.063*
C170.8352 (3)0.6017 (3)0.2610 (3)0.0702 (7)
H170.91940.66720.30730.084*
C180.6816 (3)0.3529 (3)0.2460 (3)0.0567 (6)
C190.8042 (3)0.4530 (3)0.3147 (3)0.0718 (7)
H190.86690.42050.39800.086*
C200.6530 (3)0.1995 (3)0.3102 (3)0.0615 (6)
H200.71890.17380.39440.074*
C210.4159 (3)0.1482 (3)0.2941 (3)0.0641 (6)
C220.3184 (5)0.3964 (4)0.3679 (5)0.1022 (11)
H22A0.31180.43320.26040.153*
H22B0.21710.36590.39450.153*
H22C0.35010.47870.43210.153*
O10.0693 (2)0.3330 (2)0.6835 (2)0.0744 (5)
O20.1079 (2)0.2698 (2)0.46445 (18)0.0699 (5)
O30.8131 (2)0.0794 (2)0.5477 (2)0.0717 (5)
O40.9058 (2)0.2180 (3)0.7456 (2)0.0807 (6)
O50.7603 (2)0.7965 (2)0.08141 (19)0.0666 (5)
O60.5370 (2)0.6126 (2)0.0536 (2)0.0718 (5)
O70.3145 (3)0.1471 (3)0.1902 (3)0.0887 (6)
O80.4310 (3)0.2649 (2)0.3923 (3)0.0874 (6)
N10.5617 (2)0.0216 (2)0.7210 (2)0.0583 (5)
N20.6856 (3)0.1066 (3)0.7687 (2)0.0703 (6)
H20.68890.14490.85910.084*
N30.5424 (3)0.0995 (2)0.2565 (2)0.0588 (5)
N40.5318 (3)0.0368 (3)0.3347 (2)0.0673 (6)
H4A0.60020.05040.41020.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.081 (2)0.116 (3)0.097 (2)0.042 (2)0.0291 (18)0.017 (2)
C20.099 (2)0.0901 (19)0.0422 (12)0.0300 (16)0.0048 (12)0.0068 (12)
C30.0583 (14)0.0597 (13)0.0518 (12)0.0102 (11)0.0027 (10)0.0076 (10)
C40.0675 (15)0.0741 (15)0.0496 (12)0.0091 (13)0.0129 (11)0.0103 (11)
C50.0705 (15)0.0721 (15)0.0427 (11)0.0089 (13)0.0001 (11)0.0165 (11)
C60.0577 (13)0.0558 (12)0.0471 (11)0.0071 (11)0.0046 (10)0.0112 (9)
C70.0587 (13)0.0585 (13)0.0436 (11)0.0117 (11)0.0016 (9)0.0081 (9)
C80.0587 (13)0.0552 (13)0.0422 (10)0.0105 (11)0.0015 (10)0.0090 (9)
C90.0674 (15)0.0662 (14)0.0452 (11)0.0133 (12)0.0054 (11)0.0177 (10)
C100.0615 (14)0.0592 (13)0.0566 (13)0.0099 (11)0.0093 (11)0.0135 (10)
C110.0677 (17)0.092 (2)0.090 (2)0.0219 (15)0.0067 (15)0.0067 (16)
C120.091 (2)0.0815 (19)0.0730 (17)0.0176 (17)0.0081 (15)0.0207 (14)
C130.089 (2)0.105 (2)0.106 (2)0.0075 (19)0.053 (2)0.038 (2)
C140.0481 (12)0.0640 (14)0.0422 (11)0.0168 (11)0.0008 (9)0.0126 (10)
C150.0551 (13)0.0624 (14)0.0448 (11)0.0102 (11)0.0017 (10)0.0110 (10)
C160.0486 (12)0.0607 (13)0.0496 (11)0.0114 (10)0.0014 (9)0.0102 (10)
C170.0685 (16)0.0735 (17)0.0653 (15)0.0014 (13)0.0223 (13)0.0166 (13)
C180.0585 (13)0.0636 (14)0.0504 (12)0.0180 (11)0.0002 (10)0.0132 (10)
C190.0718 (17)0.0781 (18)0.0643 (15)0.0126 (14)0.0234 (13)0.0233 (13)
C200.0662 (15)0.0662 (15)0.0537 (12)0.0176 (13)0.0069 (11)0.0184 (11)
C210.0727 (16)0.0660 (16)0.0561 (13)0.0164 (14)0.0075 (12)0.0091 (11)
C220.111 (3)0.071 (2)0.128 (3)0.0024 (19)0.041 (2)0.0078 (19)
N10.0612 (12)0.0607 (11)0.0540 (11)0.0133 (9)0.0076 (10)0.0181 (8)
N20.0719 (13)0.0897 (16)0.0546 (11)0.0293 (12)0.0013 (10)0.0319 (10)
N30.0676 (13)0.0635 (12)0.0486 (10)0.0196 (11)0.0029 (9)0.0168 (9)
N40.0769 (14)0.0669 (13)0.0583 (11)0.0081 (11)0.0087 (10)0.0205 (10)
O10.0711 (11)0.0905 (13)0.0677 (11)0.0342 (10)0.0122 (9)0.0139 (10)
O20.0782 (11)0.0920 (12)0.0454 (8)0.0393 (10)0.0027 (8)0.0183 (8)
O30.0715 (12)0.0859 (12)0.0610 (10)0.0180 (10)0.0011 (8)0.0244 (9)
O40.0763 (13)0.0995 (14)0.0718 (12)0.0382 (11)0.0003 (10)0.0232 (10)
O50.0733 (11)0.0656 (11)0.0592 (9)0.0022 (9)0.0081 (8)0.0193 (8)
O60.0687 (11)0.0774 (12)0.0671 (10)0.0021 (9)0.0223 (9)0.0287 (9)
O70.0872 (14)0.0865 (14)0.0891 (14)0.0035 (11)0.0180 (12)0.0127 (11)
O80.1069 (16)0.0683 (12)0.0869 (13)0.0002 (11)0.0003 (12)0.0223 (10)
Geometric parameters (Å, º) top
C1—O11.429 (3)C12—H12B0.9600
C1—H1A0.9600C12—H12C0.9600
C1—H1B0.9600C13—O61.402 (4)
C1—H1C0.9600C13—H13A0.9600
C2—O21.407 (3)C13—H13B0.9600
C2—H2A0.9600C13—H13C0.9600
C2—H2B0.9600C14—O61.363 (3)
C2—H2C0.9600C15—O51.359 (3)
C3—O11.355 (3)C15—C171.375 (3)
C3—C41.382 (3)C15—C141.407 (3)
C4—H40.9300C16—C141.374 (3)
C5—C41.381 (4)C16—H160.9300
C5—H50.9300C17—H170.9300
C6—C51.375 (3)C18—C191.380 (4)
C6—C71.411 (3)C18—C161.404 (3)
C6—C91.467 (3)C18—C201.461 (3)
C7—H70.9300C19—C171.389 (4)
C8—C71.363 (3)C19—H190.9300
C8—O21.369 (3)C20—N31.271 (3)
C8—C31.412 (3)C20—H200.9300
C9—N11.272 (3)C21—O71.200 (3)
C9—H90.9300C21—N41.336 (4)
C10—O31.204 (3)C21—O81.349 (3)
C10—O41.339 (3)C22—O81.422 (4)
C10—N21.347 (3)C22—H22A0.9600
C11—O41.438 (4)C22—H22B0.9600
C11—H11A0.9600C22—H22C0.9600
C11—H11B0.9600N1—N21.375 (3)
C11—H11C0.9600N2—H20.8600
C12—O51.425 (3)N3—N41.377 (3)
C12—H12A0.9600N4—H4A0.8600
O1—C1—H1A109.5O6—C13—H13B109.5
O1—C1—H1B109.5H13A—C13—H13B109.5
H1A—C1—H1B109.5O6—C13—H13C109.5
O1—C1—H1C109.5H13A—C13—H13C109.5
H1A—C1—H1C109.5H13B—C13—H13C109.5
H1B—C1—H1C109.5O6—C14—C16125.9 (2)
O2—C2—H2A109.5O6—C14—C15113.64 (19)
O2—C2—H2B109.5C16—C14—C15120.47 (19)
H2A—C2—H2B109.5O5—C15—C17124.6 (2)
O2—C2—H2C109.5O5—C15—C14116.08 (18)
H2A—C2—H2C109.5C17—C15—C14119.4 (2)
H2B—C2—H2C109.5C14—C16—C18119.9 (2)
O1—C3—C4126.0 (2)C14—C16—H16120.0
O1—C3—C8115.39 (19)C18—C16—H16120.0
C4—C3—C8118.6 (2)C15—C17—C19120.2 (2)
C5—C4—C3120.5 (2)C15—C17—H17119.9
C5—C4—H4119.7C19—C17—H17119.9
C3—C4—H4119.7C19—C18—C16119.2 (2)
C6—C5—C4121.0 (2)C19—C18—C20118.1 (2)
C6—C5—H5119.5C16—C18—C20122.6 (2)
C4—C5—H5119.5C18—C19—C17120.9 (2)
C5—C6—C7119.0 (2)C18—C19—H19119.6
C5—C6—C9119.85 (19)C17—C19—H19119.6
C7—C6—C9121.2 (2)N3—C20—C18123.1 (2)
C8—C7—C6120.1 (2)N3—C20—H20118.5
C8—C7—H7119.9C18—C20—H20118.5
C6—C7—H7119.9O7—C21—N4127.2 (3)
C7—C8—O2124.6 (2)O7—C21—O8124.9 (3)
C7—C8—C3120.68 (19)N4—C21—O8107.8 (2)
O2—C8—C3114.69 (19)O8—C22—H22A109.5
N1—C9—C6121.68 (18)O8—C22—H22B109.5
N1—C9—H9119.2H22A—C22—H22B109.5
C6—C9—H9119.2O8—C22—H22C109.5
O3—C10—O4124.9 (2)H22A—C22—H22C109.5
O3—C10—N2126.3 (2)H22B—C22—H22C109.5
O4—C10—N2108.8 (2)C9—N1—N2115.30 (18)
O4—C11—H11A109.5C10—N2—N1120.23 (19)
O4—C11—H11B109.5C10—N2—H2119.9
H11A—C11—H11B109.5N1—N2—H2119.9
O4—C11—H11C109.5C20—N3—N4114.63 (19)
H11A—C11—H11C109.5C21—N4—N3120.4 (2)
H11B—C11—H11C109.5C21—N4—H4A119.8
O5—C12—H12A109.5N3—N4—H4A119.8
O5—C12—H12B109.5C3—O1—C1118.0 (2)
H12A—C12—H12B109.5C8—O2—C2117.77 (18)
O5—C12—H12C109.5C10—O4—C11117.2 (2)
H12A—C12—H12C109.5C15—O5—C12118.1 (2)
H12B—C12—H12C109.5C14—O6—C13118.5 (2)
O6—C13—H13A109.5C21—O8—C22116.6 (3)
O2—C8—C3—O11.1 (3)C17—C15—C14—C161.2 (3)
C7—C8—C3—C41.2 (3)C18—C16—C14—O6178.9 (2)
O2—C8—C3—C4178.8 (2)C18—C16—C14—C150.2 (3)
C7—C8—C3—O1178.9 (2)O5—C15—C14—O61.9 (3)
C8—C3—C4—C50.5 (4)C17—C15—C14—O6178.0 (2)
C6—C5—C4—C30.6 (4)O5—C15—C14—C16178.9 (2)
O1—C3—C4—C5179.6 (2)C19—C18—C16—C140.3 (3)
C7—C6—C5—C41.0 (4)C20—C18—C16—C14178.1 (2)
C9—C6—C5—C4179.3 (2)O5—C15—C17—C19178.4 (3)
O2—C8—C7—C6179.2 (2)C14—C15—C17—C191.6 (4)
C3—C8—C7—C60.8 (3)C18—C19—C17—C151.1 (4)
C5—C6—C7—C80.3 (3)C16—C18—C19—C170.1 (4)
C9—C6—C7—C8180.0 (2)C20—C18—C19—C17178.6 (3)
C5—C6—C9—N1173.5 (2)C19—C18—C20—N3179.3 (2)
C7—C6—C9—N16.8 (4)C16—C18—C20—N30.8 (4)
C6—C9—N1—N2179.4 (2)C18—C20—N3—N4178.5 (2)
O3—C10—N2—N12.1 (4)O7—C21—N4—N31.5 (4)
O4—C10—N2—N1178.7 (2)O8—C21—N4—N3178.0 (2)
C9—N1—N2—C10178.3 (2)C20—N3—N4—C21176.9 (2)
C4—C3—O1—C12.6 (4)C17—C15—O5—C124.1 (4)
C8—C3—O1—C1177.3 (3)C14—C15—O5—C12175.8 (2)
C7—C8—O2—C215.2 (4)C16—C14—O6—C135.7 (4)
C3—C8—O2—C2164.8 (2)C15—C14—O6—C13175.1 (3)
O3—C10—O4—C110.3 (4)O7—C21—O8—C220.8 (4)
N2—C10—O4—C11178.9 (2)N4—C21—O8—C22179.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O5i0.862.072.902 (3)164
N2—H2···O6i0.862.543.153 (3)129
N4—H4A···O30.862.132.968 (3)164
C11—H11A···O30.962.332.701 (4)102
C19—H19···O2ii0.932.553.337 (3)143
C13—H13A···Cg1iii0.962.943.531 (4)121
Symmetry codes: (i) x, y1, z+1; (ii) x+1, y, z; (iii) x, y, z1.

Experimental details

Crystal data
Chemical formulaC11H14N2O4
Mr238.24
Crystal system, space groupTriclinic, 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)
V3)624.71 (14)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.23 × 0.21 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.971, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
3471, 2172, 1985
Rint0.013
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.080, 1.04
No. of reflections2172
No. of parameters314
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N2—H2···O5i0.862.072.902 (3)163.5
N2—H2···O6i0.862.543.153 (3)128.9
N4—H4A···O30.862.132.968 (3)164.2
C11—H11A···O30.962.332.701 (4)101.9
C19—H19···O2ii0.932.553.337 (3)142.6
C13—H13A···Cg1iii0.962.943.531 (4)121.00
Symmetry codes: (i) x, y1, z+1; (ii) x+1, y, z; (iii) x, y, z1.
 

Acknowledgements

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

References

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First citationBruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationHadjoudis, E., Vittorakis, M. & Moustakali-Mavridis, J. (1987). Tetrahedron, 43, 1345–1360.  CrossRef CAS Web of Science Google Scholar
First citationParashar, R. K., Sharma, R. C., Kumar, A. & Mohanm, G. (1988). Inorg. Chim Acta, 151, 201–208.  CrossRef CAS Web of Science Google Scholar
First citationShang, Z.-H., Zhang, H.-L. & Ding, Y. (2007). Acta Cryst. E63, o3394.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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