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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 7| July 2009| Pages o1566-o1567

4-Cyclo­butyl­amino-3-nitro­benzoic acid

aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my

(Received 5 May 2009; accepted 5 June 2009; online 13 June 2009)

The asymmetric unit of the title compound, C11H12N2O4, contains two crystallographically independent mol­ecules with similar geometries. Both mol­ecules contain an intra­molecular N—H⋯O hydrogen bond. The dihedral angles between the benzene ring and the mean plane of the cyclo­butane ring are 38.29 (7) and 57.04 (8)° in the two mol­ecules, and the nitro group is twisted slightly away from the plane of the benzene ring [dihedral angles = 9.15 (12) and 9.55 (12)° in the two mol­ecules]. In the crystal, the independent mol­ecules are linked into dimers by O—H⋯O hydrogen bonds between their carboxyl groups, and C—H⋯O and C—H⋯π inter­actions are formed between dimers.

Related literature

For the biological activity of benzimidazole derivatives, see: Wright (1951[Wright, J. B. (1951). Chem. Rev. 48, 397-541.]); Singh et al. (2009[Singh, S., Bharti, N. & Mohapatra, P. P. (2009). Chem. Rev. 109, 1900-1947.]). For details of the synthesis, see: Narendra Babu et al. (2009a[Narendra Babu, S. N., Abdul Rahim, A. S., Abd Hamid, S., Quah, C. K. & Fun, H.-K. (2009a). Acta Cryst. E65, o1079.],b[Narendra Babu, S. N., Abdul Rahim, A. S., Osman, H., Jebas, S. R. & Fun, H.-K. (2009b). Acta Cryst. E65, o1122-o1123.]); Ishida et al. (2006[Ishida, T., Suzuki, T., Hirashima, S., Mizutani, K., Yoshida, A., Ando, I., Ikeda, S., Adachi, T. & Hashimoto, H. (2006). Bioorg. Med. Chem. Lett. 16, 1859-1863.]).

[Scheme 1]

Experimental

Crystal data
  • C11H12N2O4

  • Mr = 236.23

  • Triclinic, [P \overline 1]

  • a = 9.8555 (2) Å

  • b = 10.5308 (2) Å

  • c = 10.9110 (2) Å

  • α = 74.860 (1)°

  • β = 78.265 (1)°

  • γ = 84.826 (1)°

  • V = 1069.44 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 110 K

  • 0.37 × 0.23 × 0.21 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.960, Tmax = 0.976

  • 29344 measured reflections

  • 7670 independent reflections

  • 6094 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.139

  • S = 1.05

  • 7670 reflections

  • 315 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.68 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2A—H1OA⋯O1Bi 0.81 1.76 2.5608 (13) 166
O2B—H1OB⋯O1Aii 0.83 1.89 2.7118 (12) 170
N2A—H1NA⋯O4A 0.89 (2) 1.93 (2) 2.6332 (13) 135.3 (17)
N2B—H1NB⋯O4B 0.80 (2) 2.05 (2) 2.6432 (13) 130.7 (18)
C8B—H8BB⋯O4Aiii 0.97 2.54 3.4613 (16) 158
C8B—H8BACg1iv 0.97 2.83 3.4744 (13) 124
Symmetry codes: (i) x, y+1, z-1; (ii) x, y-1, z+1; (iii) -x, -y+1, -z+1; (iv) -x+1, -y+1, -z+1. Cg1 is the centroid of the C1B–C6B benzene ring.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Multi functionalized benzimidazole remains as an attractive scaffold to display essential binding moieties against many validated biological targets (Wright, 1951; Singh et al., 2009). This heterocycle is commonly accessed via nitro benzoic acid derivatives, which form a part of our current synthetic chemistry work (Narendra Babu et al., 2009a&b; Ishida et al., 2006). Recently, we have successfully synthesized the title compound, whose crystal structure is described here.

The asymmetric unit contains two crystallographically independent molecules (Fig. 1), A and B with similar geometries. An intramolecular N–H···O hydrogen bond is formed in both independent molecules. The dihedral angle formed by the C1A–C6A benzene ring and C7A–C10A cyclobutane is 38.29 (7)° and that between the C1B–C6B benzene ring and C7B–C10B cyclobutane is 57.04 (8)°. The nitro group in each molecule is slightly twisted away from the attached benzene ring as indicated by the torsion angle O3—N1—C1—C2, being 7.97 (15)° and 7.80 (14)° in molecules A and B, respectively.

The crystal packing (Fig. 2) is consolidated by intermolecular O—H···O and C—H···O hydrogen bonds. Molecules are linked by O—H···O hydrogen bonds between their carboxylate groups to form dimers. The crystal structure is further stabilized by C—H···π (Table 1) interactions involving the C1B–C6B benzene ring (centroid Cg1) and short O4B···O4B contacts (symmetry code: 2 - x, 1 - y, 1 - z) with distance = 2.8957 (12) Å which is shorter than the sum of van der Waals radii of the O atoms.

Related literature top

For the biological activity of benzimidazole derivatives, see: Wright (1951); Singh et al. (2009). For details of the synthesis, see: Narendra Babu et al. (2009a,b); Ishida et al. (2006).

Experimental top

The title compound was obtained by refluxing ethyl 4-(cyclobutylamino)-3-nitro-benzoate (0.2 g, 0.0007 mol) and KOH (0.08 g, 0.0015 mol) in aqueous ethanol (5 ml) for 3 h. After completion of the reaction, ethanol was distilled off and the reaction mixture was diluted with water (5 ml). The aqueous layer was washed with dichloromethane (2 × 5 ml) and acidified with concentrated hydrochloric acid to afford a yellow solid. Yellow crystals suitable for X-ray analysis were obtained after recrystallization of the crude product with hot ethyl acetate.

Refinement top

H atoms bound to N and O atoms were located from difference Fourier maps. Atoms H1NA and H1NB were refined freely, while atoms H1OA and H1OB were refined as riding on the parent O atom with Uiso(H) = 1.5 Ueq(O). The remaining H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.98 Å and Uiso(H) = 1.2 or 1.5 Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing 50% probability displacement ellipsoids for non-H atoms. The dashed lines indicate hydrogen bonds.
[Figure 2] Fig. 2. Packing diagram viewed along the a axis. Intermolecular interactions are shown as dashed lines.
4-Cyclobutylamino-3-nitrobenzoic acid top
Crystal data top
C11H12N2O4Z = 4
Mr = 236.23F(000) = 496
Triclinic, P1Dx = 1.467 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8555 (2) ÅCell parameters from 9970 reflections
b = 10.5308 (2) Åθ = 2.1–34.1°
c = 10.9110 (2) ŵ = 0.11 mm1
α = 74.860 (1)°T = 110 K
β = 78.265 (1)°Block, yellow
γ = 84.826 (1)°0.37 × 0.23 × 0.21 mm
V = 1069.44 (4) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer
7670 independent reflections
Radiation source: fine-focus sealed tube6094 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ϕ and ω scansθmax = 32.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1314
Tmin = 0.960, Tmax = 0.976k = 1515
29344 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.079P)2 + 0.2648P]
where P = (Fo2 + 2Fc2)/3
7670 reflections(Δ/σ)max < 0.001
315 parametersΔρmax = 0.68 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C11H12N2O4γ = 84.826 (1)°
Mr = 236.23V = 1069.44 (4) Å3
Triclinic, P1Z = 4
a = 9.8555 (2) ÅMo Kα radiation
b = 10.5308 (2) ŵ = 0.11 mm1
c = 10.9110 (2) ÅT = 110 K
α = 74.860 (1)°0.37 × 0.23 × 0.21 mm
β = 78.265 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
7670 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
6094 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.976Rint = 0.027
29344 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.68 e Å3
7670 reflectionsΔρmin = 0.25 e Å3
315 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat operating at 110.0 (1) K. Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
O1A0.41436 (8)0.68803 (8)0.08160 (8)0.02153 (17)
O2A0.24499 (9)0.80673 (8)0.01400 (9)0.02327 (17)
H1OA0.29690.86710.02080.035*
O3A0.16874 (10)0.63616 (9)0.25760 (10)0.0315 (2)
O4A0.22880 (9)0.43744 (8)0.28295 (10)0.02693 (19)
N1A0.14187 (9)0.52458 (9)0.24261 (9)0.01836 (18)
N2A0.04041 (10)0.25875 (8)0.22307 (9)0.01699 (17)
C1A0.00540 (10)0.49386 (10)0.17520 (10)0.01442 (17)
C2A0.07959 (10)0.59982 (10)0.11780 (10)0.01488 (18)
H2AA0.04690.68400.12400.018*
C3A0.21236 (10)0.58164 (10)0.05150 (10)0.01456 (17)
C4A0.26136 (10)0.45284 (10)0.04592 (10)0.01638 (18)
H4AA0.35070.43940.00230.020*
C5A0.17907 (11)0.34694 (10)0.10395 (10)0.01650 (18)
H5AA0.21470.26290.10010.020*
C6A0.04005 (10)0.36263 (9)0.17013 (9)0.01448 (17)
C7A0.00443 (12)0.12158 (10)0.24008 (10)0.01755 (19)
H7AA0.08050.10070.28850.021*
C8A0.03497 (12)0.06059 (10)0.12218 (11)0.0202 (2)
H8AA0.00600.11050.04960.024*
H8AB0.13250.03960.09470.024*
C9A0.04894 (13)0.05907 (11)0.20696 (11)0.0229 (2)
H9AA0.11560.08590.16520.027*
H9AB0.00800.13370.24360.027*
C10A0.11338 (13)0.02595 (11)0.30201 (11)0.0235 (2)
H10A0.20460.06420.29020.028*
H10B0.11310.01790.39200.028*
C11A0.29658 (10)0.69811 (10)0.00959 (10)0.01597 (18)
O1B0.37447 (9)0.02069 (9)0.91518 (9)0.02540 (18)
O2B0.55207 (10)0.08564 (8)0.81460 (9)0.02504 (18)
H1OB0.51070.15370.85470.038*
O3B0.91441 (9)0.17243 (8)0.51738 (8)0.02423 (18)
O4B0.93948 (9)0.37738 (8)0.50719 (9)0.02599 (19)
N1B0.87317 (9)0.27498 (9)0.54966 (9)0.01787 (17)
N2B0.73342 (10)0.51524 (9)0.61428 (9)0.01799 (17)
C1B0.74352 (10)0.27632 (10)0.63934 (10)0.01530 (18)
C2B0.68286 (11)0.15493 (10)0.69549 (10)0.01604 (18)
H2BA0.72770.07900.67620.019*
C3B0.55681 (11)0.14668 (10)0.77957 (10)0.01613 (18)
C4B0.48894 (11)0.26379 (10)0.80444 (10)0.01760 (19)
H4BA0.40310.25950.85950.021*
C5B0.54711 (11)0.38380 (10)0.74909 (10)0.01740 (19)
H5BA0.49910.45910.76690.021*
C6B0.67903 (10)0.39638 (10)0.66502 (10)0.01536 (18)
C7B0.65788 (11)0.63794 (10)0.62404 (10)0.01690 (18)
H7BA0.62320.63850.71470.020*
C8B0.54323 (12)0.68736 (12)0.54265 (12)0.0239 (2)
H8BA0.55340.65220.46740.029*
H8BB0.44970.67800.59260.029*
C9B0.59819 (13)0.82720 (11)0.51283 (13)0.0249 (2)
H9BA0.60700.87490.42280.030*
H9BB0.54830.88030.56930.030*
C10B0.73574 (12)0.76364 (10)0.55077 (11)0.0208 (2)
H10C0.80660.75250.47800.025*
H10D0.77190.80580.60590.025*
C11B0.49108 (11)0.01977 (10)0.83986 (10)0.01689 (19)
H1NA0.124 (2)0.2777 (18)0.2638 (18)0.038 (5)*
H1NB0.805 (2)0.5208 (18)0.5636 (18)0.035 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0161 (3)0.0208 (4)0.0240 (4)0.0040 (3)0.0020 (3)0.0025 (3)
O2A0.0194 (4)0.0128 (3)0.0356 (5)0.0029 (3)0.0012 (3)0.0049 (3)
O3A0.0237 (4)0.0165 (4)0.0500 (6)0.0019 (3)0.0087 (4)0.0125 (4)
O4A0.0160 (4)0.0180 (4)0.0415 (5)0.0058 (3)0.0052 (3)0.0044 (3)
N1A0.0148 (4)0.0143 (4)0.0234 (4)0.0015 (3)0.0000 (3)0.0027 (3)
N2A0.0180 (4)0.0103 (4)0.0205 (4)0.0027 (3)0.0002 (3)0.0020 (3)
C1A0.0128 (4)0.0122 (4)0.0169 (4)0.0012 (3)0.0014 (3)0.0021 (3)
C2A0.0150 (4)0.0114 (4)0.0173 (4)0.0014 (3)0.0031 (3)0.0015 (3)
C3A0.0140 (4)0.0120 (4)0.0167 (4)0.0026 (3)0.0029 (3)0.0011 (3)
C4A0.0141 (4)0.0151 (4)0.0194 (4)0.0003 (3)0.0025 (3)0.0039 (3)
C5A0.0166 (4)0.0123 (4)0.0200 (4)0.0002 (3)0.0033 (3)0.0032 (3)
C6A0.0164 (4)0.0116 (4)0.0149 (4)0.0020 (3)0.0036 (3)0.0014 (3)
C7A0.0228 (5)0.0102 (4)0.0193 (4)0.0021 (3)0.0047 (4)0.0019 (3)
C8A0.0239 (5)0.0149 (4)0.0215 (5)0.0003 (4)0.0036 (4)0.0043 (4)
C9A0.0327 (6)0.0137 (4)0.0242 (5)0.0039 (4)0.0082 (4)0.0049 (4)
C10A0.0311 (6)0.0140 (4)0.0233 (5)0.0083 (4)0.0007 (4)0.0030 (4)
C11A0.0149 (4)0.0140 (4)0.0183 (4)0.0026 (3)0.0036 (3)0.0018 (3)
O1B0.0196 (4)0.0211 (4)0.0306 (4)0.0075 (3)0.0025 (3)0.0011 (3)
O2B0.0304 (4)0.0145 (4)0.0284 (4)0.0049 (3)0.0012 (3)0.0040 (3)
O3B0.0265 (4)0.0204 (4)0.0240 (4)0.0019 (3)0.0033 (3)0.0082 (3)
O4B0.0185 (4)0.0176 (4)0.0358 (5)0.0053 (3)0.0044 (3)0.0016 (3)
N1B0.0166 (4)0.0166 (4)0.0183 (4)0.0021 (3)0.0013 (3)0.0017 (3)
N2B0.0160 (4)0.0133 (4)0.0221 (4)0.0024 (3)0.0012 (3)0.0011 (3)
C1B0.0137 (4)0.0145 (4)0.0164 (4)0.0030 (3)0.0017 (3)0.0016 (3)
C2B0.0170 (4)0.0133 (4)0.0174 (4)0.0025 (3)0.0031 (3)0.0025 (3)
C3B0.0164 (4)0.0134 (4)0.0177 (4)0.0040 (3)0.0029 (3)0.0014 (3)
C4B0.0154 (4)0.0164 (4)0.0191 (4)0.0025 (3)0.0011 (3)0.0022 (4)
C5B0.0157 (4)0.0146 (4)0.0200 (5)0.0016 (3)0.0015 (3)0.0022 (3)
C6B0.0153 (4)0.0134 (4)0.0169 (4)0.0020 (3)0.0043 (3)0.0015 (3)
C7B0.0185 (4)0.0129 (4)0.0186 (4)0.0014 (3)0.0043 (4)0.0017 (3)
C8B0.0188 (5)0.0209 (5)0.0304 (6)0.0031 (4)0.0089 (4)0.0008 (4)
C9B0.0241 (5)0.0166 (5)0.0308 (6)0.0003 (4)0.0080 (4)0.0018 (4)
C10B0.0221 (5)0.0131 (4)0.0270 (5)0.0038 (4)0.0080 (4)0.0011 (4)
C11B0.0168 (4)0.0145 (4)0.0186 (4)0.0039 (3)0.0028 (3)0.0022 (3)
Geometric parameters (Å, º) top
O1A—C11A1.2752 (13)O1B—C11B1.2705 (13)
O2A—C11A1.2763 (12)O2B—C11B1.2812 (13)
O2A—H1OA0.815O2B—H1OB0.829
O3A—N1A1.2264 (12)O3B—N1B1.2316 (12)
O4A—N1A1.2439 (12)O4B—N1B1.2440 (12)
N1A—C1A1.4484 (13)N1B—C1B1.4442 (13)
N2A—C6A1.3413 (13)N2B—C6B1.3412 (13)
N2A—C7A1.4472 (13)N2B—C7B1.4497 (13)
N2A—H1NA0.888 (19)N2B—H1NB0.802 (19)
C1A—C2A1.3889 (14)C1B—C2B1.3952 (14)
C1A—C6A1.4254 (13)C1B—C6B1.4313 (14)
C2A—C3A1.3836 (14)C2B—C3B1.3808 (14)
C2A—H2AA0.930C2B—H2BA0.930
C3A—C4A1.4105 (13)C3B—C4B1.4122 (14)
C3A—C11A1.4728 (14)C3B—C11B1.4704 (14)
C4A—C5A1.3740 (14)C4B—C5B1.3718 (14)
C4A—H4AA0.930C4B—H4BA0.930
C5A—C6A1.4300 (14)C5B—C6B1.4254 (14)
C5A—H5AA0.930C5B—H5BA0.930
C7A—C10A1.5347 (15)C7B—C10B1.5365 (15)
C7A—C8A1.5483 (15)C7B—C8B1.5482 (15)
C7A—H7AA0.980C7B—H7BA0.980
C8A—C9A1.5477 (16)C8B—C9B1.5458 (17)
C8A—H8AA0.970C8B—H8BA0.970
C8A—H8AB0.970C8B—H8BB0.970
C9A—C10A1.5476 (16)C9B—C10B1.5418 (16)
C9A—H9AA0.970C9B—H9BA0.970
C9A—H9AB0.970C9B—H9BB0.970
C10A—H10A0.970C10B—H10C0.970
C10A—H10B0.970C10B—H10D0.970
C11A—O2A—H1OA111.9C11B—O2B—H1OB114.1
O3A—N1A—O4A121.83 (9)O3B—N1B—O4B122.07 (9)
O3A—N1A—C1A119.01 (9)O3B—N1B—C1B118.88 (9)
O4A—N1A—C1A119.16 (9)O4B—N1B—C1B119.05 (9)
C6A—N2A—C7A126.24 (9)C6B—N2B—C7B123.78 (9)
C6A—N2A—H1NA114.6 (12)C6B—N2B—H1NB118.5 (13)
C7A—N2A—H1NA118.1 (12)C7B—N2B—H1NB116.5 (13)
C2A—C1A—C6A121.97 (9)C2B—C1B—C6B122.19 (9)
C2A—C1A—N1A115.91 (9)C2B—C1B—N1B116.19 (9)
C6A—C1A—N1A122.12 (9)C6B—C1B—N1B121.58 (9)
C3A—C2A—C1A120.77 (9)C3B—C2B—C1B120.48 (9)
C3A—C2A—H2AA119.6C3B—C2B—H2BA119.8
C1A—C2A—H2AA119.6C1B—C2B—H2BA119.8
C2A—C3A—C4A118.77 (9)C2B—C3B—C4B118.68 (9)
C2A—C3A—C11A118.30 (9)C2B—C3B—C11B121.37 (9)
C4A—C3A—C11A122.93 (9)C4B—C3B—C11B119.92 (9)
C5A—C4A—C3A121.02 (9)C5B—C4B—C3B121.34 (10)
C5A—C4A—H4AA119.5C5B—C4B—H4BA119.3
C3A—C4A—H4AA119.5C3B—C4B—H4BA119.3
C4A—C5A—C6A121.66 (9)C4B—C5B—C6B121.84 (9)
C4A—C5A—H5AA119.2C4B—C5B—H5BA119.1
C6A—C5A—H5AA119.2C6B—C5B—H5BA119.1
N2A—C6A—C1A123.24 (9)N2B—C6B—C5B120.09 (9)
N2A—C6A—C5A120.98 (9)N2B—C6B—C1B124.48 (9)
C1A—C6A—C5A115.78 (9)C5B—C6B—C1B115.42 (9)
N2A—C7A—C10A113.66 (9)N2B—C7B—C10B115.50 (9)
N2A—C7A—C8A119.61 (9)N2B—C7B—C8B118.69 (9)
C10A—C7A—C8A89.08 (8)C10B—C7B—C8B88.50 (8)
N2A—C7A—H7AA110.9N2B—C7B—H7BA110.8
C10A—C7A—H7AA110.9C10B—C7B—H7BA110.8
C8A—C7A—H7AA110.9C8B—C7B—H7BA110.8
C9A—C8A—C7A88.22 (8)C9B—C8B—C7B87.84 (8)
C9A—C8A—H8AA113.9C9B—C8B—H8BA114.0
C7A—C8A—H8AA113.9C7B—C8B—H8BA114.0
C9A—C8A—H8AB113.9C9B—C8B—H8BB114.0
C7A—C8A—H8AB113.9C7B—C8B—H8BB114.0
H8AA—C8A—H8AB111.2H8BA—C8B—H8BB111.2
C10A—C9A—C8A88.63 (8)C10B—C9B—C8B88.40 (8)
C10A—C9A—H9AA113.9C10B—C9B—H9BA113.9
C8A—C9A—H9AA113.9C8B—C9B—H9BA113.9
C10A—C9A—H9AB113.9C10B—C9B—H9BB113.9
C8A—C9A—H9AB113.9C8B—C9B—H9BB113.9
H9AA—C9A—H9AB111.1H9BA—C9B—H9BB111.1
C7A—C10A—C9A88.71 (9)C7B—C10B—C9B88.40 (8)
C7A—C10A—H10A113.9C7B—C10B—H10C113.9
C9A—C10A—H10A113.9C9B—C10B—H10C113.9
C7A—C10A—H10B113.9C7B—C10B—H10D113.9
C9A—C10A—H10B113.9C9B—C10B—H10D113.9
H10A—C10A—H10B111.1H10C—C10B—H10D111.1
O1A—C11A—O2A123.11 (10)O1B—C11B—O2B122.99 (10)
O1A—C11A—C3A120.54 (9)O1B—C11B—C3B117.51 (9)
O2A—C11A—C3A116.35 (9)O2B—C11B—C3B119.49 (9)
O3A—N1A—C1A—C2A7.97 (15)O3B—N1B—C1B—C2B7.80 (14)
O4A—N1A—C1A—C2A171.59 (10)O4B—N1B—C1B—C2B172.39 (10)
O3A—N1A—C1A—C6A170.85 (10)O3B—N1B—C1B—C6B169.99 (10)
O4A—N1A—C1A—C6A9.59 (15)O4B—N1B—C1B—C6B9.82 (15)
C6A—C1A—C2A—C3A0.82 (16)C6B—C1B—C2B—C3B0.32 (16)
N1A—C1A—C2A—C3A179.65 (9)N1B—C1B—C2B—C3B178.10 (9)
C1A—C2A—C3A—C4A1.57 (15)C1B—C2B—C3B—C4B1.83 (15)
C1A—C2A—C3A—C11A178.78 (9)C1B—C2B—C3B—C11B179.98 (10)
C2A—C3A—C4A—C5A0.59 (15)C2B—C3B—C4B—C5B1.38 (16)
C11A—C3A—C4A—C5A179.77 (10)C11B—C3B—C4B—C5B179.61 (10)
C3A—C4A—C5A—C6A1.17 (16)C3B—C4B—C5B—C6B0.62 (16)
C7A—N2A—C6A—C1A169.40 (10)C7B—N2B—C6B—C5B9.26 (16)
C7A—N2A—C6A—C5A10.71 (16)C7B—N2B—C6B—C1B169.59 (10)
C2A—C1A—C6A—N2A179.01 (10)C4B—C5B—C6B—N2B179.01 (10)
N1A—C1A—C6A—N2A2.23 (16)C4B—C5B—C6B—C1B2.04 (15)
C2A—C1A—C6A—C5A0.88 (15)C2B—C1B—C6B—N2B179.51 (10)
N1A—C1A—C6A—C5A177.88 (9)N1B—C1B—C6B—N2B2.83 (16)
C4A—C5A—C6A—N2A178.03 (10)C2B—C1B—C6B—C5B1.59 (15)
C4A—C5A—C6A—C1A1.86 (15)N1B—C1B—C6B—C5B176.07 (9)
C6A—N2A—C7A—C10A179.08 (10)C6B—N2B—C7B—C10B175.71 (10)
C6A—N2A—C7A—C8A75.85 (14)C6B—N2B—C7B—C8B72.54 (14)
N2A—C7A—C8A—C9A134.34 (10)N2B—C7B—C8B—C9B138.08 (10)
C10A—C7A—C8A—C9A17.43 (9)C10B—C7B—C8B—C9B19.62 (9)
C7A—C8A—C9A—C10A17.28 (9)C7B—C8B—C9B—C10B19.55 (9)
N2A—C7A—C10A—C9A139.60 (9)N2B—C7B—C10B—C9B140.96 (10)
C8A—C7A—C10A—C9A17.42 (8)C8B—C7B—C10B—C9B19.66 (9)
C8A—C9A—C10A—C7A17.43 (9)C8B—C9B—C10B—C7B19.70 (9)
C2A—C3A—C11A—O1A173.48 (10)C2B—C3B—C11B—O1B179.36 (10)
C4A—C3A—C11A—O1A6.87 (16)C4B—C3B—C11B—O1B1.19 (15)
C2A—C3A—C11A—O2A6.58 (14)C2B—C3B—C11B—O2B0.37 (16)
C4A—C3A—C11A—O2A173.06 (10)C4B—C3B—C11B—O2B178.54 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H1OA···O1Bi0.811.762.5608 (13)166
O2B—H1OB···O1Aii0.831.892.7118 (12)170
N2A—H1NA···O4A0.89 (2)1.93 (2)2.6332 (13)135.3 (17)
N2B—H1NB···O4B0.80 (2)2.05 (2)2.6432 (13)130.7 (18)
C8B—H8BB···O4Aiii0.972.543.4613 (16)158
C8B—H8BA···Cg1iv0.972.833.4744 (13)124
Symmetry codes: (i) x, y+1, z1; (ii) x, y1, z+1; (iii) x, y+1, z+1; (iv) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC11H12N2O4
Mr236.23
Crystal system, space groupTriclinic, P1
Temperature (K)110
a, b, c (Å)9.8555 (2), 10.5308 (2), 10.9110 (2)
α, β, γ (°)74.860 (1), 78.265 (1), 84.826 (1)
V3)1069.44 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.37 × 0.23 × 0.21
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.960, 0.976
No. of measured, independent and
observed [I > 2σ(I)] reflections
29344, 7670, 6094
Rint0.027
(sin θ/λ)max1)0.756
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.139, 1.05
No. of reflections7670
No. of parameters315
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.68, 0.25

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H1OA···O1Bi0.811.762.5608 (13)166
O2B—H1OB···O1Aii0.831.892.7118 (12)170
N2A—H1NA···O4A0.89 (2)1.93 (2)2.6332 (13)135.3 (17)
N2B—H1NB···O4B0.80 (2)2.05 (2)2.6432 (13)130.7 (18)
C8B—H8BB···O4Aiii0.972.543.4613 (16)158
C8B—H8BA···Cg1iv0.972.833.4744 (13)124
Symmetry codes: (i) x, y+1, z1; (ii) x, y1, z+1; (iii) x, y+1, z+1; (iv) x+1, y+1, z+1.
 

Footnotes

Additional correspondence author, e-mail: aisyah@usm.my.

§Thomson Reuters ResearcherID: A-5525-2009.

Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

SNNB, ASAR and HO are grateful to Universiti Sains Malaysia (USM) for funding the synthetic chemistry work under the University Research Grant (1001/PFARMASI/815026). SNNB acknowledges USM for a Postdoctoral Research Fellowship. HKF and CKQ thank USM for the Research University Golden Goose Grant (1001/PFIZIK/811012). CKQ thanks USM for a Research Fellowship.

References

First citationBruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationIshida, T., Suzuki, T., Hirashima, S., Mizutani, K., Yoshida, A., Ando, I., Ikeda, S., Adachi, T. & Hashimoto, H. (2006). Bioorg. Med. Chem. Lett. 16, 1859–1863.  Web of Science CrossRef PubMed CAS Google Scholar
First citationNarendra Babu, S. N., Abdul Rahim, A. S., Abd Hamid, S., Quah, C. K. & Fun, H.-K. (2009a). Acta Cryst. E65, o1079.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationNarendra Babu, S. N., Abdul Rahim, A. S., Osman, H., Jebas, S. R. & Fun, H.-K. (2009b). Acta Cryst. E65, o1122–o1123.  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
First citationSingh, S., Bharti, N. & Mohapatra, P. P. (2009). Chem. Rev. 109, 1900–1947.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 65| Part 7| July 2009| Pages o1566-o1567
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