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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 11| November 2008| Pages o2175-o2176

3,4-Dimeth­­oxy-N-(3-nitro­benzyl­­idene)aniline

aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran, and cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 28 September 2008; accepted 20 October 2008; online 22 October 2008)

The title compound, C15H14N2O4, has two crystallographically independent mol­ecules in the asymmetric unit. In both mol­ecules, the nitro and the two meth­oxy substituents are coplanar with the benzene rings to which they are attached. The benzene rings are nearly coplanar, with dihedral angles between the two benzene rings of 10.39 (8) and 5.95 (8)° in the two mol­ecules. The two independent mol­ecules in the asymmetric unit are rotated with respect to each other such that the dihedral angles between equivalent benzene rings are 49.11 (8) and 63.93 (8)°. In the crystal structure, inter­molecular C—H⋯O hydrogen-bond contacts and a weak C—H⋯π inter­action are observed.

Related literature

For general background, see: Arora et al. (2002[Arora, K., Gupta, A. & Agarwal, D. D. (2002). Asian J. Chem. 14, 1611-1615.]); Desai et al. (2001[Desai, S. B., Desai, P. B. & Desai, K. R. (2001). Heterocycl. Commun. 7, 83-90.]); El-masry et al. (2000[El-masry, A. H., Fahmy, H. H. & Abdelwahed, S. H. A. (2000). Molecules, 5, 1429-1438.]); Jarrahpour & Khalili (2006[Jarrahpour, A. A. & Khalili, D. (2006). Molecules, 11, 59-63.]); Jarrahpour et al. (2004[Jarrahpour, A. A., Motamedifar, M., Pakshir, K., Hadi, N. & Zarei, M. (2004). Molecules, 9, 815-824.]); More et al. (2001[More, P. G., Bhalvankar, R. B. & Pattar, S. C. (2001). J. Indian Chem. Soc. 78, 474-475.]); Phatak et al. (2000[Phatak, P., Jolly, V. S. & Sharma, K. P. (2000). Orient. J. Chem. 16, 493-494.]); Samadhiya & Halve (2001[Samadhiya, S. & Halve, A. (2001). Orient. J. Chem. 17, 119-122.]); Singh & Dash (1988[Singh, W. M. & Dash, B. C. (1988). Pesticides, 22, 33-37.]); Tanaka & Shiraishi (2000[Tanaka, K. & Shiraishi, R. (2000). Green Chem. 2, 272-273.]). For related structures, see: Akkurt et al. (2005[Akkurt, M., Karaca, S., Jarrahpour, A. A., Zarei, M. & Büyükgüngör, O. (2005). Acta Cryst. E61, o776-o778.], 2008[Akkurt, M., Jarrahpour, A., Aye, M., Gençaslan, M. & Büyükgüngör, O. (2008). Acta Cryst. E64, o2087.]).

[Scheme 1]

Experimental

Crystal data
  • C15H14N2O4

  • Mr = 286.28

  • Triclinic, [P \overline 1]

  • a = 8.6345 (8) Å

  • b = 8.6540 (8) Å

  • c = 19.2304 (17) Å

  • α = 96.629 (7)°

  • β = 97.338 (7)°

  • γ = 102.075 (7)°

  • V = 1378.6 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 296 K

  • 0.78 × 0.36 × 0.07 mm

Data collection
  • Stoe IPDS II diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.925, Tmax = 0.993

  • 21166 measured reflections

  • 6330 independent reflections

  • 3703 reflections with I > 2σ(I)

  • Rint = 0.065

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.119

  • S = 0.98

  • 6330 reflections

  • 380 parameters

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.13 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8A⋯O7i 0.96 2.39 3.268 (3) 152
C14—H14⋯O5ii 0.93 2.55 3.206 (2) 128
C22—H22A⋯O1iii 0.96 2.60 3.410 (3) 143
C28—H28⋯O4iv 0.93 2.57 3.222 (2) 128
C18—H18⋯Cg1 0.93 2.89 3.654 (2) 141
Symmetry codes: (i) x+1, y+1, z-1; (ii) x, y-1, z; (iii) -x+1, -y+1, -z; (iv) -x-1, -y, -z+1. Cg1 is the centroid of the C10–C15 ring.

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Rizzi, R. (1999). J. Appl. Cryst. 32, 339-340.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

Schiff bases are widely used for synthetic purposes both by organic and inorganic chemists (Arora et al., 2002) and have uses as biological, analytical, polymer and liquid crystalline materials (Tanaka & Shiraishi, 2000). Schiff bases are reported to show a variety of biological activities such as antibacterial (Jarrahpour & Khalili, 2006; Jarrahpour et al., 2004; El-masry et al., 2000), antifungal (More et al., 2001; Singh & Dash, 1988), anticancer (Desai et al., 2001; Phatak et al., 2000) and herbicidal activities (Samadhiya & Halve, 2001). As an extension of our work on Schiff bases, we report here the crystal structure of the title compound (I).

The two molecules of (I) in the asymetric unit are shown in Fig. 1. In both molecules, the NO2 and the two –OCH3 substituents are coplanar with the benzene rings and the dihedral angles between the two benzene rings are 10.39 (8)° for C1–C6 and C10–C15 in molecule 1, and 5.95 (8)° for C16–C21 and C25–C30 in molecule 2. The dihedral angles between tequivalent benzene rings in the two independent molecules in the asymmetric unit are 49.11 (8)° for C1–C6 and C16–C21, and 63.93 (8)° for C10–C15 and C25–C30.

In the crystal structure, the packing is stabilized by intermolecular C—H···O type hydrogen contacts and a weak C—H···π interaction (Table 1 and Fig. 2).

Related literature top

For general background, see: Arora et al. (2002); Desai et al. (2001); El-masry et al. (2000); Jarrahpour & Khalili (2006); Jarrahpour et al. (2004); More et al. (2001); Phatak et al. (2000); Samadhiya & Halve (2001); Singh & Dash (1988); Tanaka & Shiraishi (2000). For related structures, see: Akkurt et al. (2005, 2008). Cg1 is the centroid of the C10–C15 ring.

Experimental top

A mixture of 3,4-dimethoxyaniline (3 mmol) and 3-nitrobenzaldehyde(3 mmol) was refluxed in EtOH for 4 h. After cooling the solution, the precipitate formed was filtered off and washed with ethanol to give the pure Schiff base as a dark yellow solid [yield 75%, m.p. 389–391 K]. IR(KBr) (cm-1) 1616.2 (CN). 1H-NMR (CDCl3) δ (p.p.m.) 3.92,3.94 (2 OCH3, 2 s, 6H), 6.87–8.72 (ArH, m, 7H), 8.89 (HCN, s, 1H). 13C-NMR (CDCl3) δ (p.p.m.) 55.96, 56.11 (2 OCH3), 105.62–149.47 (C=C aromatic carbons), 154.97 (CN).

Refinement top

All H atoms were positioned geometrically, with C—H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = 1.2 or 1.5Ueq(C).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. A view of the two independent molecules in the asymmetric unit of the title compound, with the atom-numbering scheme and 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. The packing and hydrogen contacts of (I) in the unitcell, down a axis. H atoms not involved in hydrogen bonding have been omitted, for clarity.
3,4-Dimethoxy-N-(3-nitrobenzylidene)aniline top
Crystal data top
C15H14N2O4Z = 4
Mr = 286.28F(000) = 600
Triclinic, P1Dx = 1.379 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.6345 (8) ÅCell parameters from 17758 reflections
b = 8.6540 (8) Åθ = 2.2–28.0°
c = 19.2304 (17) ŵ = 0.10 mm1
α = 96.629 (7)°T = 296 K
β = 97.338 (7)°Plate, yellow
γ = 102.075 (7)°0.78 × 0.36 × 0.07 mm
V = 1378.6 (2) Å3
Data collection top
Stoe IPDS II
diffractometer
6330 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus3703 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.065
Detector resolution: 6.67 pixels mm-1θmax = 27.6°, θmin = 2.2°
ω scansh = 1111
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1111
Tmin = 0.925, Tmax = 0.993l = 2424
21166 measured reflections
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)] = 0.045H-atom parameters constrained
wR(F2) = 0.119 w = 1/[σ2(Fo2) + (0.0559P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.001
6330 reflectionsΔρmax = 0.15 e Å3
380 parametersΔρmin = 0.13 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001Fc2λ3/sin(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0065 (13)
Crystal data top
C15H14N2O4γ = 102.075 (7)°
Mr = 286.28V = 1378.6 (2) Å3
Triclinic, P1Z = 4
a = 8.6345 (8) ÅMo Kα radiation
b = 8.6540 (8) ŵ = 0.10 mm1
c = 19.2304 (17) ÅT = 296 K
α = 96.629 (7)°0.78 × 0.36 × 0.07 mm
β = 97.338 (7)°
Data collection top
Stoe IPDS II
diffractometer
6330 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
3703 reflections with I > 2σ(I)
Tmin = 0.925, Tmax = 0.993Rint = 0.065
21166 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.119H-atom parameters constrained
S = 0.98Δρmax = 0.15 e Å3
6330 reflectionsΔρmin = 0.13 e Å3
380 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O10.62826 (14)0.32088 (17)0.08996 (7)0.0729 (5)
O20.49739 (15)0.47609 (18)0.17819 (7)0.0779 (5)
O30.37252 (16)0.1054 (2)0.11097 (9)0.0897 (6)
O40.39393 (17)0.0126 (2)0.20230 (8)0.0972 (6)
N10.14725 (16)0.23760 (17)0.02524 (8)0.0601 (5)
N20.31661 (18)0.04278 (19)0.15877 (9)0.0664 (6)
C10.24228 (19)0.3003 (2)0.02440 (9)0.0560 (6)
C20.39725 (19)0.2781 (2)0.02885 (9)0.0572 (6)
C30.47868 (19)0.3383 (2)0.08055 (9)0.0568 (6)
C40.4075 (2)0.4223 (2)0.12873 (9)0.0586 (6)
C50.2561 (2)0.4444 (2)0.12409 (10)0.0667 (7)
C60.1746 (2)0.3826 (2)0.07202 (10)0.0644 (6)
C70.7050 (2)0.2369 (3)0.04221 (11)0.0732 (7)
C80.4271 (3)0.5528 (3)0.23003 (13)0.0983 (10)
C90.2050 (2)0.1789 (2)0.07672 (10)0.0599 (6)
C100.10483 (19)0.1058 (2)0.12568 (9)0.0536 (6)
C110.05710 (19)0.10691 (19)0.11873 (9)0.0525 (5)
C120.14762 (19)0.03390 (19)0.16476 (9)0.0529 (5)
C130.0856 (2)0.0437 (2)0.21671 (9)0.0604 (6)
C140.0736 (2)0.0444 (2)0.22346 (10)0.0675 (7)
C150.1685 (2)0.0304 (2)0.17885 (10)0.0630 (6)
O50.06734 (14)0.60630 (14)0.26497 (6)0.0629 (4)
O60.07174 (16)0.73981 (14)0.35747 (7)0.0704 (5)
O70.4307 (2)0.31605 (19)0.63291 (10)0.1093 (7)
O80.3373 (2)0.29259 (17)0.53686 (9)0.0982 (7)
N30.19109 (17)0.23924 (16)0.45961 (7)0.0581 (5)
N40.38348 (19)0.23626 (19)0.58865 (9)0.0690 (6)
C160.1260 (2)0.33841 (18)0.41193 (9)0.0528 (5)
C170.0490 (2)0.2699 (2)0.36272 (10)0.0694 (7)
C180.0180 (2)0.3553 (2)0.31274 (10)0.0655 (7)
C190.00864 (19)0.51125 (19)0.31179 (8)0.0516 (5)
C200.06863 (19)0.58383 (18)0.36230 (9)0.0505 (5)
C210.13542 (19)0.49789 (19)0.41131 (9)0.0526 (5)
C220.1519 (3)0.5404 (2)0.21425 (11)0.0764 (8)
C230.1356 (3)0.8214 (2)0.41150 (12)0.0798 (8)
C240.2518 (2)0.2938 (2)0.51111 (9)0.0558 (6)
C250.31981 (19)0.18957 (19)0.56009 (9)0.0526 (5)
C260.31842 (19)0.02855 (19)0.55182 (9)0.0538 (5)
C270.38451 (19)0.0654 (2)0.59839 (9)0.0537 (5)
C280.4530 (2)0.0053 (2)0.65350 (9)0.0631 (7)
C290.4539 (2)0.1540 (2)0.66146 (10)0.0702 (7)
C300.3882 (2)0.2513 (2)0.61519 (10)0.0633 (6)
H20.445100.222700.003100.0690*
H50.208200.500500.155700.0800*
H60.071800.397500.069400.0770*
H7A0.808900.232600.054000.1100*
H7B0.641500.130300.045600.1100*
H7C0.716500.290900.005300.1100*
H8A0.502100.584500.261400.1470*
H8B0.398600.645600.207600.1470*
H8C0.332700.480900.256600.1470*
H90.314200.181900.083900.0720*
H110.103400.156100.083600.0630*
H130.150500.094100.246300.0730*
H140.118300.095400.258200.0810*
H150.277100.030200.184500.0760*
H170.041500.164300.362800.0830*
H180.069300.306500.279800.0790*
H210.187200.546100.444300.0630*
H22A0.187300.618500.184600.1150*
H22B0.082200.447700.185600.1150*
H22C0.243200.510800.238500.1150*
H23A0.131700.929100.402800.1200*
H23B0.073400.822700.456700.1200*
H23C0.244800.767600.411400.1200*
H240.253300.401600.518000.0670*
H260.273300.015500.515200.0650*
H280.497300.071000.684300.0760*
H290.499100.197300.698300.0840*
H300.390200.359000.621200.0760*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0571 (7)0.1085 (10)0.0671 (8)0.0268 (7)0.0286 (6)0.0354 (7)
O20.0699 (8)0.1108 (11)0.0679 (8)0.0238 (7)0.0317 (7)0.0455 (8)
O30.0671 (8)0.1186 (12)0.1004 (12)0.0323 (8)0.0288 (8)0.0475 (10)
O40.0799 (9)0.1330 (13)0.0907 (11)0.0167 (9)0.0519 (9)0.0366 (10)
N10.0573 (8)0.0702 (9)0.0606 (9)0.0152 (7)0.0256 (7)0.0221 (7)
N20.0637 (9)0.0753 (10)0.0642 (10)0.0117 (8)0.0301 (8)0.0121 (8)
C10.0561 (9)0.0598 (10)0.0555 (10)0.0099 (8)0.0216 (8)0.0144 (8)
C20.0560 (9)0.0682 (11)0.0539 (10)0.0155 (8)0.0205 (8)0.0195 (8)
C30.0518 (9)0.0680 (11)0.0534 (10)0.0112 (8)0.0188 (8)0.0132 (8)
C40.0571 (9)0.0697 (11)0.0524 (10)0.0097 (8)0.0209 (8)0.0179 (8)
C50.0624 (11)0.0797 (12)0.0653 (12)0.0183 (9)0.0176 (9)0.0284 (10)
C60.0529 (9)0.0805 (12)0.0681 (12)0.0178 (9)0.0230 (9)0.0253 (10)
C70.0606 (11)0.0953 (14)0.0749 (13)0.0283 (10)0.0218 (10)0.0271 (11)
C80.0993 (16)0.142 (2)0.0828 (16)0.0479 (15)0.0419 (13)0.0677 (16)
C90.0525 (9)0.0718 (11)0.0608 (11)0.0147 (8)0.0211 (8)0.0171 (9)
C100.0560 (9)0.0566 (10)0.0512 (10)0.0128 (7)0.0181 (8)0.0098 (7)
C110.0573 (9)0.0574 (10)0.0468 (9)0.0136 (7)0.0173 (7)0.0134 (7)
C120.0574 (9)0.0535 (9)0.0502 (9)0.0100 (7)0.0213 (8)0.0075 (7)
C130.0768 (12)0.0540 (10)0.0528 (10)0.0082 (8)0.0233 (9)0.0149 (8)
C140.0854 (13)0.0651 (11)0.0590 (11)0.0227 (9)0.0169 (10)0.0213 (9)
C150.0633 (10)0.0695 (11)0.0625 (11)0.0218 (9)0.0149 (9)0.0175 (9)
O50.0773 (8)0.0624 (7)0.0604 (7)0.0180 (6)0.0350 (6)0.0249 (6)
O60.1004 (9)0.0575 (7)0.0747 (8)0.0342 (7)0.0466 (7)0.0314 (6)
O70.1593 (15)0.0864 (10)0.1150 (13)0.0412 (10)0.0760 (12)0.0647 (10)
O80.1480 (14)0.0737 (9)0.0983 (12)0.0427 (9)0.0652 (11)0.0337 (8)
N30.0721 (9)0.0517 (8)0.0526 (8)0.0069 (7)0.0223 (7)0.0160 (6)
N40.0789 (10)0.0673 (10)0.0732 (11)0.0208 (8)0.0290 (9)0.0341 (8)
C160.0634 (10)0.0474 (9)0.0478 (9)0.0052 (7)0.0166 (8)0.0129 (7)
C170.1022 (14)0.0473 (10)0.0685 (12)0.0185 (9)0.0394 (11)0.0166 (8)
C180.0878 (13)0.0570 (10)0.0609 (11)0.0204 (9)0.0349 (10)0.0134 (8)
C190.0559 (9)0.0537 (9)0.0485 (9)0.0097 (7)0.0181 (8)0.0153 (7)
C200.0560 (9)0.0498 (9)0.0507 (9)0.0136 (7)0.0157 (7)0.0164 (7)
C210.0605 (9)0.0531 (9)0.0496 (9)0.0142 (7)0.0205 (8)0.0141 (7)
C220.0904 (13)0.0826 (13)0.0715 (13)0.0247 (11)0.0485 (11)0.0257 (10)
C230.1131 (16)0.0639 (11)0.0861 (14)0.0428 (11)0.0515 (13)0.0273 (10)
C240.0638 (10)0.0492 (9)0.0559 (10)0.0071 (7)0.0170 (8)0.0160 (8)
C250.0535 (9)0.0561 (10)0.0480 (9)0.0059 (7)0.0117 (7)0.0143 (7)
C260.0574 (9)0.0591 (10)0.0483 (9)0.0113 (8)0.0173 (8)0.0159 (8)
C270.0538 (9)0.0614 (10)0.0496 (9)0.0114 (7)0.0139 (7)0.0204 (8)
C280.0650 (10)0.0766 (13)0.0535 (11)0.0128 (9)0.0224 (9)0.0250 (9)
C290.0775 (12)0.0793 (13)0.0613 (12)0.0184 (10)0.0334 (10)0.0155 (10)
C300.0711 (11)0.0608 (11)0.0612 (11)0.0132 (9)0.0225 (9)0.0121 (9)
Geometric parameters (Å, º) top
O1—C31.363 (2)C7—H7A0.9600
O1—C71.418 (3)C8—H8C0.9600
O2—C41.365 (2)C8—H8B0.9600
O2—C81.404 (3)C8—H8A0.9600
O3—N21.218 (2)C9—H90.9300
O4—N21.216 (2)C11—H110.9300
O5—C221.427 (3)C13—H130.9300
O5—C191.363 (2)C14—H140.9300
O6—C231.422 (3)C15—H150.9300
O6—C201.369 (2)C16—C171.373 (3)
O7—N41.214 (2)C16—C211.401 (2)
O8—N41.208 (2)C17—C181.390 (3)
N1—C11.419 (2)C18—C191.371 (2)
N1—C91.258 (2)C19—C201.408 (2)
N2—C121.468 (2)C20—C211.377 (2)
N3—C241.268 (2)C24—C251.470 (2)
N3—C161.416 (2)C25—C261.387 (2)
N4—C271.471 (2)C25—C301.385 (2)
C1—C21.403 (2)C26—C271.376 (2)
C1—C61.369 (2)C27—C281.380 (2)
C2—C31.378 (2)C28—C291.371 (2)
C3—C41.401 (2)C29—C301.387 (3)
C4—C51.373 (3)C17—H170.9300
C5—C61.389 (3)C18—H180.9300
C9—C101.467 (2)C21—H210.9300
C10—C151.391 (2)C22—H22A0.9600
C10—C111.390 (2)C22—H22B0.9600
C11—C121.376 (2)C22—H22C0.9600
C12—C131.380 (2)C23—H23A0.9600
C13—C141.366 (3)C23—H23B0.9600
C14—C151.383 (3)C23—H23C0.9600
C2—H20.9300C24—H240.9300
C5—H50.9300C26—H260.9300
C6—H60.9300C28—H280.9300
C7—H7B0.9600C29—H290.9300
C7—H7C0.9600C30—H300.9300
O1···O22.575 (2)C21···H23B2.7600
O1···C22i3.410 (3)C22···H182.5300
O2···O12.575 (2)C23···H26v2.8400
O2···C22i3.220 (3)C23···H212.5000
O3···C7ii3.373 (3)C24···H212.6600
O4···C29iii3.322 (2)C28···H14xii3.0600
O4···C28iii3.222 (2)C29···H23Cxiii3.0400
O4···C3iv3.337 (2)H2···H7B2.2800
O5···C14v3.206 (2)H2···O3x2.8500
O5···C30vi3.285 (2)H2···C72.4900
O5···O62.5677 (18)H2···H7C2.2900
O6···O52.5677 (18)H2···H92.0600
O7···C8vii3.268 (3)H2···C92.6400
O8···C23viii3.274 (3)H5···C82.5100
O1···H22Ai2.6000H5···H8B2.2600
O2···H22Ci2.6400H5···O5ix2.8800
O3···H8Bix2.7400H5···H8C2.3400
O3···H9ii2.9100H6···H7Aii2.4900
O3···H112.4100H7A···H6x2.4900
O3···H7Biv2.8000H7B···H22.2800
O3···H2ii2.8500H7B···C22.7200
O3···H7Cii2.8200H7B···O3iv2.8000
O4···H28iii2.5700H7C···H11x2.5700
O4···H132.4400H7C···O3x2.8200
O4···H29iii2.7600H7C···C22.7300
O5···H14v2.5500H7C···H22.2900
O5···H5ix2.8800H7C···C5i2.9900
O6···H13v2.8000H7C···C6i2.8700
O7···H282.4400H8A···O7xi2.3900
O7···H30viii2.8900H8A···H22Ci2.5100
O7···H8Avii2.3900H8B···C52.7200
O8···H23Cviii2.7100H8B···H52.2600
O8···H24viii2.8800H8B···O3ix2.7400
O8···H21viii2.7500H8C···C19ix3.0200
O8···H262.4400H8C···C52.7500
N2···C2iv3.403 (2)H8C···H52.3400
N2···C3iv3.389 (2)H8C···C20ix2.7700
N4···C24iii3.380 (2)H9···H152.4800
N1···H112.5700H9···O3x2.9100
N3···H23Bvi2.8000H9···C22.5400
N3···H23Aviii2.9500H9···H22.0600
N3···H262.5700H11···C7ii2.9900
C2···N2iv3.403 (2)H11···H7Cii2.5700
C2···C3i3.594 (2)H11···O32.4100
C3···C2i3.594 (2)H11···N12.5700
C3···O4iv3.337 (2)H13···O6viii2.8000
C3···N2iv3.389 (2)H13···O42.4400
C7···O3x3.373 (3)H14···O5viii2.5500
C8···O7xi3.268 (3)H14···C28xii3.0600
C13···C183.598 (2)H15···H92.4800
C14···O5viii3.206 (2)H17···C133.0900
C18···C133.598 (2)H17···H23Aviii2.2800
C19···C30vi3.504 (2)H18···C133.0800
C20···C24vi3.341 (2)H18···C222.5300
C20···C25vi3.552 (2)H18···H22B2.3000
C21···C24vi3.498 (2)H18···H22C2.3500
C22···O2i3.220 (3)H21···O8v2.7500
C22···O1i3.410 (3)H21···C232.5000
C23···O8v3.274 (3)H21···C242.6600
C24···C21vi3.498 (2)H21···H23B2.3600
C24···C27iii3.599 (2)H21···H23C2.2200
C24···N4iii3.380 (2)H21···H242.0500
C24···C20vi3.341 (2)H22A···O1i2.6000
C25···C20vi3.552 (2)H22B···C113.0100
C25···C26iii3.582 (2)H22B···C182.7500
C26···C25iii3.582 (2)H22B···H182.3000
C26···C26iii3.403 (2)H22C···C182.7700
C27···C24iii3.599 (2)H22C···H182.3500
C28···O4iii3.222 (2)H22C···O2i2.6400
C29···O4iii3.322 (2)H22C···C8i3.0300
C30···C19vi3.504 (2)H22C···H8Ai2.5100
C30···O5vi3.285 (2)H23A···N3v2.9500
C2···H7C2.7300H23A···C17v3.1000
C2···H7B2.7200H23A···H17v2.2800
C2···H92.5400H23B···C212.7600
C5···H7Ci2.9900H23B···H212.3600
C5···H8B2.7200H23B···N3vi2.8000
C5···H8C2.7500H23C···O8v2.7100
C6···H7Ci2.8700H23C···C212.6900
C7···H22.4900H23C···H212.2200
C7···H11x2.9900H23C···C29xiii3.0400
C8···H52.5100H24···O8v2.8800
C8···H22Ci3.0300H24···C212.5500
C9···H22.6400H24···H212.0500
C11···H22B3.0100H24···H302.4600
C13···H173.0900H26···O82.4400
C13···H183.0800H26···N32.5700
C17···H23Aviii3.1000H26···C23viii2.8400
C18···H22C2.7700H28···O72.4400
C18···H22B2.7500H28···O4iii2.5700
C19···H8Cix3.0200H29···O4iii2.7600
C20···H8Cix2.7700H30···O7v2.8900
C21···H242.5500H30···H242.4600
C21···H23C2.6900
C3—O1—C7117.12 (14)C14—C13—H13121.00
C4—O2—C8117.65 (16)C12—C13—H13121.00
C19—O5—C22117.37 (13)C13—C14—H14120.00
C20—O6—C23116.66 (14)C15—C14—H14120.00
C1—N1—C9121.85 (15)C14—C15—H15119.00
O3—N2—O4123.16 (17)C10—C15—H15119.00
O4—N2—C12118.00 (16)N3—C16—C17116.25 (14)
O3—N2—C12118.84 (16)N3—C16—C21125.11 (15)
C16—N3—C24121.57 (14)C17—C16—C21118.65 (15)
O7—N4—O8122.33 (17)C16—C17—C18121.30 (16)
O7—N4—C27118.52 (16)C17—C18—C19120.26 (16)
O8—N4—C27119.14 (16)O5—C19—C18125.71 (15)
N1—C1—C2124.00 (15)O5—C19—C20115.11 (14)
N1—C1—C6117.13 (15)C18—C19—C20119.18 (15)
C2—C1—C6118.83 (16)O6—C20—C19115.11 (14)
C1—C2—C3120.08 (16)O6—C20—C21124.80 (15)
O1—C3—C2124.52 (16)C19—C20—C21120.09 (15)
C2—C3—C4120.24 (16)C16—C21—C20120.52 (16)
O1—C3—C4115.23 (15)N3—C24—C25121.11 (15)
O2—C4—C3115.77 (15)C24—C25—C26121.08 (15)
C3—C4—C5119.56 (16)C24—C25—C30120.06 (15)
O2—C4—C5124.67 (16)C26—C25—C30118.85 (16)
C4—C5—C6119.80 (17)C25—C26—C27119.36 (16)
C1—C6—C5121.48 (16)N4—C27—C26118.80 (15)
N1—C9—C10121.83 (16)N4—C27—C28118.86 (15)
C11—C10—C15118.52 (16)C26—C27—C28122.34 (16)
C9—C10—C11120.57 (15)C27—C28—C29118.05 (16)
C9—C10—C15120.89 (16)C28—C29—C30120.76 (17)
C10—C11—C12118.74 (16)C25—C30—C29120.65 (16)
C11—C12—C13122.91 (16)C16—C17—H17119.00
N2—C12—C11117.96 (15)C18—C17—H17119.00
N2—C12—C13119.11 (15)C17—C18—H18120.00
C12—C13—C14118.19 (16)C19—C18—H18120.00
C13—C14—C15120.30 (17)C16—C21—H21120.00
C10—C15—C14121.31 (16)C20—C21—H21120.00
C3—C2—H2120.00O5—C22—H22A109.00
C1—C2—H2120.00O5—C22—H22B109.00
C4—C5—H5120.00O5—C22—H22C109.00
C6—C5—H5120.00H22A—C22—H22B110.00
C5—C6—H6119.00H22A—C22—H22C109.00
C1—C6—H6119.00H22B—C22—H22C109.00
O1—C7—H7C109.00O6—C23—H23A109.00
O1—C7—H7A109.00O6—C23—H23B109.00
O1—C7—H7B109.00O6—C23—H23C110.00
H7B—C7—H7C109.00H23A—C23—H23B109.00
H7A—C7—H7B109.00H23A—C23—H23C109.00
H7A—C7—H7C110.00H23B—C23—H23C109.00
O2—C8—H8A109.00N3—C24—H24119.00
O2—C8—H8C109.00C25—C24—H24119.00
H8A—C8—H8B109.00C25—C26—H26120.00
O2—C8—H8B110.00C27—C26—H26120.00
H8B—C8—H8C109.00C27—C28—H28121.00
H8A—C8—H8C109.00C29—C28—H28121.00
N1—C9—H9119.00C28—C29—H29120.00
C10—C9—H9119.00C30—C29—H29120.00
C10—C11—H11121.00C25—C30—H30120.00
C12—C11—H11121.00C29—C30—H30120.00
C7—O1—C3—C21.0 (3)N1—C9—C10—C15174.86 (17)
C7—O1—C3—C4179.84 (17)C11—C10—C15—C141.0 (3)
C8—O2—C4—C53.2 (3)C9—C10—C15—C14177.38 (17)
C8—O2—C4—C3176.40 (17)C15—C10—C11—C120.2 (2)
C22—O5—C19—C182.8 (2)C9—C10—C11—C12178.56 (16)
C22—O5—C19—C20177.79 (16)C10—C11—C12—C131.5 (3)
C23—O6—C20—C216.2 (3)C10—C11—C12—N2177.18 (15)
C23—O6—C20—C19174.41 (17)N2—C12—C13—C14177.09 (16)
C1—N1—C9—C10176.43 (16)C11—C12—C13—C141.5 (3)
C9—N1—C1—C6170.48 (17)C12—C13—C14—C150.3 (3)
C9—N1—C1—C211.8 (3)C13—C14—C15—C100.9 (3)
O4—N2—C12—C133.4 (2)C17—C16—C21—C200.0 (3)
O3—N2—C12—C13176.91 (17)C21—C16—C17—C180.4 (3)
O3—N2—C12—C114.4 (2)N3—C16—C21—C20179.64 (16)
O4—N2—C12—C11175.31 (17)N3—C16—C17—C18179.29 (16)
C24—N3—C16—C216.9 (3)C16—C17—C18—C190.2 (3)
C16—N3—C24—C25179.68 (16)C17—C18—C19—C200.4 (3)
C24—N3—C16—C17173.53 (17)C17—C18—C19—O5178.99 (16)
O8—N4—C27—C28173.22 (18)C18—C19—C20—O6179.79 (15)
O7—N4—C27—C286.1 (3)O5—C19—C20—C21178.67 (15)
O7—N4—C27—C26174.45 (18)O5—C19—C20—O60.7 (2)
O8—N4—C27—C266.2 (3)C18—C19—C20—C210.8 (3)
N1—C1—C6—C5178.02 (16)C19—C20—C21—C160.6 (3)
C6—C1—C2—C30.1 (3)O6—C20—C21—C16179.96 (15)
N1—C1—C2—C3177.54 (16)N3—C24—C25—C260.6 (3)
C2—C1—C6—C50.2 (3)N3—C24—C25—C30178.79 (17)
C1—C2—C3—O1178.89 (16)C24—C25—C26—C27179.43 (16)
C1—C2—C3—C40.2 (3)C30—C25—C26—C270.1 (2)
C2—C3—C4—O2179.55 (16)C26—C25—C30—C290.2 (3)
O1—C3—C4—O20.4 (2)C24—C25—C30—C29179.50 (16)
C2—C3—C4—C50.1 (3)C25—C26—C27—N4179.48 (16)
O1—C3—C4—C5179.23 (16)C25—C26—C27—C280.1 (3)
O2—C4—C5—C6179.20 (17)N4—C27—C28—C29179.54 (16)
C3—C4—C5—C60.4 (3)C26—C27—C28—C290.1 (3)
C4—C5—C6—C10.5 (3)C27—C28—C29—C300.2 (3)
N1—C9—C10—C113.5 (3)C28—C29—C30—C250.2 (3)
Symmetry codes: (i) x+1, y+1, z; (ii) x1, y, z; (iii) x1, y, z+1; (iv) x, y, z; (v) x, y+1, z; (vi) x, y+1, z+1; (vii) x1, y1, z+1; (viii) x, y1, z; (ix) x, y+1, z; (x) x+1, y, z; (xi) x+1, y+1, z1; (xii) x, y, z+1; (xiii) x1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···O7xi0.962.393.268 (3)152
C14—H14···O5viii0.932.553.206 (2)128
C22—H22A···O1i0.962.603.410 (3)143
C28—H28···O4iii0.932.573.222 (2)128
C18—H18···Cg10.932.893.654 (2)141
Symmetry codes: (i) x+1, y+1, z; (iii) x1, y, z+1; (viii) x, y1, z; (xi) x+1, y+1, z1.

Experimental details

Crystal data
Chemical formulaC15H14N2O4
Mr286.28
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)8.6345 (8), 8.6540 (8), 19.2304 (17)
α, β, γ (°)96.629 (7), 97.338 (7), 102.075 (7)
V3)1378.6 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.78 × 0.36 × 0.07
Data collection
DiffractometerStoe IPDS II
diffractometer
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.925, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
21166, 6330, 3703
Rint0.065
(sin θ/λ)max1)0.652
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.119, 0.98
No. of reflections6330
No. of parameters380
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.13

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···O7i0.962.393.268 (3)152
C14—H14···O5ii0.932.553.206 (2)128
C22—H22A···O1iii0.962.603.410 (3)143
C28—H28···O4iv0.932.573.222 (2)128
C18—H18···Cg10.932.893.654 (2)141
Symmetry codes: (i) x+1, y+1, z1; (ii) x, y1, z; (iii) x+1, y+1, z; (iv) x1, y, z+1.
 

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS II diffractometer (purchased under grant F.279 of the University Research Fund).

References

First citationAkkurt, M., Jarrahpour, A., Aye, M., Gençaslan, M. & Büyükgüngör, O. (2008). Acta Cryst. E64, o2087.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationAkkurt, M., Karaca, S., Jarrahpour, A. A., Zarei, M. & Büyükgüngör, O. (2005). Acta Cryst. E61, o776–o778.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationAltomare, A., Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Rizzi, R. (1999). J. Appl. Cryst. 32, 339–340.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationArora, K., Gupta, A. & Agarwal, D. D. (2002). Asian J. Chem. 14, 1611–1615.  CAS Google Scholar
First citationDesai, S. B., Desai, P. B. & Desai, K. R. (2001). Heterocycl. Commun. 7, 83–90.  CrossRef CAS Google Scholar
First citationEl-masry, A. H., Fahmy, H. H. & Abdelwahed, S. H. A. (2000). Molecules, 5, 1429–1438.  CAS Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationJarrahpour, A. A. & Khalili, D. (2006). Molecules, 11, 59–63.  Web of Science CrossRef PubMed CAS Google Scholar
First citationJarrahpour, A. A., Motamedifar, M., Pakshir, K., Hadi, N. & Zarei, M. (2004). Molecules, 9, 815–824.  Web of Science CrossRef PubMed CAS Google Scholar
First citationMore, P. G., Bhalvankar, R. B. & Pattar, S. C. (2001). J. Indian Chem. Soc. 78, 474–475.  CAS Google Scholar
First citationPhatak, P., Jolly, V. S. & Sharma, K. P. (2000). Orient. J. Chem. 16, 493–494.  CAS Google Scholar
First citationSamadhiya, S. & Halve, A. (2001). Orient. J. Chem. 17, 119–122.  CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSingh, W. M. & Dash, B. C. (1988). Pesticides, 22, 33–37.  Google Scholar
First citationStoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.  Google Scholar
First citationTanaka, K. & Shiraishi, R. (2000). Green Chem. 2, 272–273.  Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 11| November 2008| Pages o2175-o2176
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds