3-(2,3-Dimethyl-5-oxo-1-phenyl-2,5-di­hydro-1H-pyrazol-4-yl)sydnone

Goh, J.H.; Fun, H.-K.; Nithinchandra; Kalluraya, B.

doi:10.1107/S1600536810015667

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Pages o1251-o1252

https://doi.org/10.1107/S1600536810015667

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3-(2,3-Dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)sydnone

Jia Hao Goh,^a ‡ Hoong-Kun Fun,^a ^*§ Nithinchandra ^b and B. Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 9 April 2010; accepted 28 April 2010; online 8 May 2010)

In the title sydnone compound [systematic name: 3-(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)-1,2,3-oxadiazol-3-ium-5-olate], C₁₃H₁₂N₄O₃, the oxadiazole and pyrazole rings are essentially planar [maximum deviations = 0.006 (1) and 0.019 (1) Å, respectively] and are inclined at interplanar angles of 37.84 (4) and 46.60 (4)°, respectively, with respect to the benzene ring. In the crystal, adjacent molecules are interconnected into a three-dimensional supramolecular network via intermolecular C—H⋯O hydrogen bonds. Weak intermolecular π–π aromatic stacking interactions [centroid–centroid distance = 3.5251 (5) Å] further stabilize the crystal packing.

Related literature

For general background to and applications of sydnone derivatives, see: Baker et al. (1949 ); Hedge et al. (2008 ); Rai et al. (2008 ). For the preparation of 3-aryl sydnones, see Kalluraya et al. (2004 ); Rai et al. (2008). For related structures, see: Baker & Ollis (1957 ); Goh et al. (2009a ,b , 2010a ,b ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₃H₁₂N₄O₃
M_r = 272.27
Monoclinic, P 2₁ /c
a = 10.6525 (3) Å
b = 7.3014 (3) Å
c = 15.6828 (4) Å
β = 93.982 (1)°
V = 1216.83 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.56 × 0.17 × 0.08 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.941, T_max = 0.992
44010 measured reflections
6426 independent reflections
4895 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.125
S = 1.04
6426 reflections
229 parameters
All H-atom parameters refined
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O3ⁱ	0.981 (14)	2.492 (13)	3.2155 (10)	130.4 (10)
C11—H11A⋯O2ⁱ	0.944 (13)	2.543 (13)	3.4163 (10)	153.9 (11)
C12—H12B⋯O2ⁱⁱ	0.984 (13)	2.369 (13)	3.3022 (10)	158.1 (11)
C13—H13A⋯O3ⁱⁱⁱ	0.958 (14)	2.516 (15)	3.3606 (10)	147.0 (12)
Symmetry codes: (i) -x+1, -y+2, -z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+2, -y+2, -z.

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810015667/sj2767sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015667/sj2767Isup2.hkl

checkCIF report

Comment top

Sydnones constitute a well-defined class of mesoionic compounds that contain a 1,2,3-oxadiazole ring system. The introduction of the concept of mesoionic structure for certain heterocyclic compounds in the year 1949 has proved to be fruitful development in heterocyclic chemistry (Baker et al., 1949). The study of sydnones still remains a field of interest because of their electronic structure and also because of the various types of biological activities displayed by some of them. Interest in sydnone derivatives has also been encouraged by the discovery that they exhibit various pharmacological activities (Hedge et al., 2008; Rai et al., 2008).

3-aryl sydnones are prepared by the cyclisation of N-nitroso-N-aryl glycines with acetic anhydride. These N-nitroso-N-aryl glycines were obtained by the nitrosation of N-substituted glycines. The N-substituted glycine was obtained by the hydrolysis of corresponding ester with sodiumhydroxide. The ester is in turn obtained by the reaction of appropriately substituted aniline with ethyl aceto acetate in absolute ethanol medium employing anhydrous sodium acetate as the catalyst (Kalluraya et al., 2004; Rai et al., 2008)

In the title sydnone compound (Fig. 1), the 1,2,3-oxadiazole (N3/N4/O1/C10/C11) and pyrazole (N1/N2/C7-C9) rings are essentially planar, with maximum deviations of 0.006 (1) and -0.019 (1) Å, respectively, at atoms N4 and N1. These two rings are inclined at interplanar angles of 37.84 (4) and 46.60 (4)°, respectively, with the C1-C6 benzene ring. As reported previously (Goh et al., 2010a,b), the exocyclic C10–O3 bond length of 1.2205 (9) Å is inconsistent with the formulation of Baker & Ollis (1957), which involves the delocalization of a positive charge in the 1,2,3-oxadiazole ring, and a negative charge in the exocyclic oxygen. The bond lengths (Allen et al., 1987) and angles are within normal range and comparable to those observed in closely related pyrazole (Goh et al., 2009a,b) and sydnone (Goh et al., 2010a,b) structures.

In the crystal packing, C1—H1A···O3, C13—H13A···O3, C11—H11A···O2 and C12—H12B···O2 hydrogen bonds (Table 1) form two different pairs of intermolecular bifurcated acceptor hydrogen bonds, which link the molecules into a three-dimensional supramolecular network. The crystal packing is further stabilized by weak intermolecular π–π aromatic stacking interactions [Cg1···Cg2ⁱⁱ = 3.5251 (5) Å, (ii) = -x+1, y-1/2, -z+1/2 where Cg1 and Cg2 are centroids of pyrazole and benzene rings, respectively].

Related literature top

For general background to and applications of sydnone derivatives, see: Baker et al. (1949); Hedge et al. (2008); Rai et al. (2008). For the preparation of 3-aryl sydnones, see Kalluraya et al. (2004); Rai et al. (2008). For related structures, see: Baker & Ollis (1957); Goh et al. (2009a,b, 2010a,b). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(nitroso) amino]acetic acid (0.1 mol) was heated with acetic anhydride (0.5 mol) on a water bath for 2–4 h, the reaction mixture was kept aside at room temperature for overnight. It was then poured into ice cold water, filtered and washed with water, sodium bicarbonate solution (5 %) and again with water. The solid product was dried and crystallized from benzene. Single crystals suitable for X-ray analysis were obtained from a 1:2 mixture of DMF and ethanol by slow evaporation.

Structure description top

For general background to and applications of sydnone derivatives, see: Baker et al. (1949); Hedge et al. (2008); Rai et al. (2008). For the preparation of 3-aryl sydnones, see Kalluraya et al. (2004); Rai et al. (2008). For related structures, see: Baker & Ollis (1957); Goh et al. (2009a,b, 2010a,b). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis, showing a three-dimensional supramolecular network. Hydrogen atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.

3-(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)-1,2,3- oxadiazol-3-ium-5-olate top

Crystal data top

C₁₃H₁₂N₄O₃	F(000) = 568
M_r = 272.27	D_x = 1.486 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9368 reflections
a = 10.6525 (3) Å	θ = 3.1–37.4°
b = 7.3014 (3) Å	µ = 0.11 mm⁻¹
c = 15.6828 (4) Å	T = 100 K
β = 93.982 (1)°	Block, brown
V = 1216.83 (7) Å³	0.56 × 0.17 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	6426 independent reflections
Radiation source: fine-focus sealed tube	4895 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
φ and ω scans	θ_max = 37.6°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→18
T_min = 0.941, T_max = 0.992	k = −12→12
44010 measured reflections	l = −26→26

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	All H-atom parameters refined
S = 1.04	w = 1/[σ²(F_o²) + (0.0663P)² + 0.1919P] where P = (F_o² + 2F_c²)/3
6426 reflections	(Δ/σ)_max = 0.001
229 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₃H₁₂N₄O₃	V = 1216.83 (7) Å³
M_r = 272.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.6525 (3) Å	µ = 0.11 mm⁻¹
b = 7.3014 (3) Å	T = 100 K
c = 15.6828 (4) Å	0.56 × 0.17 × 0.08 mm
β = 93.982 (1)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	6426 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4895 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.992	R_int = 0.048
44010 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.125	All H-atom parameters refined
S = 1.04	Δρ_max = 0.55 e Å⁻³
6426 reflections	Δρ_min = −0.41 e Å⁻³
229 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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
O1	0.93586 (5)	1.20867 (9)	0.00540 (4)	0.02015 (12)
O2	0.51808 (5)	1.07724 (9)	0.11293 (4)	0.01697 (11)
O3	0.83681 (6)	1.19975 (11)	−0.12824 (4)	0.02477 (14)
N1	0.59770 (5)	0.96695 (9)	0.24595 (4)	0.01428 (11)
N2	0.71755 (6)	0.94159 (9)	0.28563 (4)	0.01458 (11)
N3	0.79599 (6)	1.09624 (9)	0.08032 (4)	0.01374 (11)
N4	0.91049 (6)	1.16505 (11)	0.08800 (4)	0.01949 (13)
C1	0.37495 (7)	0.95237 (11)	0.26642 (5)	0.01608 (13)
C2	0.27426 (7)	0.99016 (12)	0.31562 (6)	0.01978 (14)
C3	0.29319 (8)	1.07726 (13)	0.39442 (6)	0.02155 (15)
C4	0.41384 (8)	1.12975 (12)	0.42404 (5)	0.01955 (14)
C5	0.51539 (7)	1.09504 (11)	0.37507 (5)	0.01622 (13)
C6	0.49514 (6)	1.00508 (10)	0.29691 (4)	0.01404 (12)
C7	0.80407 (6)	0.97734 (10)	0.22937 (5)	0.01404 (12)
C8	0.74125 (6)	1.03529 (10)	0.15426 (4)	0.01342 (12)
C9	0.60776 (6)	1.03268 (10)	0.16264 (4)	0.01363 (12)
C10	0.83202 (7)	1.16748 (12)	−0.05217 (5)	0.01728 (13)
C11	0.74198 (7)	1.09301 (11)	−0.00008 (5)	0.01608 (13)
C12	0.73637 (7)	0.82345 (12)	0.36075 (5)	0.01818 (14)
C13	0.93987 (7)	0.94884 (12)	0.25274 (5)	0.01862 (14)
H1A	0.3617 (12)	0.8870 (19)	0.2119 (9)	0.023 (3)*
H2A	0.1903 (13)	0.953 (2)	0.2965 (9)	0.030 (3)*
H3A	0.2226 (13)	1.100 (2)	0.4312 (9)	0.031 (3)*
H4A	0.4263 (14)	1.193 (2)	0.4800 (10)	0.035 (4)*
H5A	0.5999 (12)	1.134 (2)	0.3956 (8)	0.026 (3)*
H11A	0.6593 (12)	1.0502 (18)	−0.0133 (9)	0.023 (3)*
H13A	0.9830 (14)	0.939 (2)	0.2013 (9)	0.033 (4)*
H13B	0.9704 (14)	1.055 (2)	0.2880 (10)	0.040 (4)*
H13C	0.9524 (14)	0.841 (2)	0.2879 (10)	0.036 (4)*
H12A	0.7723 (15)	0.894 (2)	0.4061 (10)	0.040 (4)*
H12B	0.6549 (12)	0.7786 (18)	0.3781 (8)	0.024 (3)*
H12C	0.7870 (14)	0.718 (2)	0.3489 (9)	0.033 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0160 (2)	0.0304 (3)	0.0140 (2)	−0.0050 (2)	0.00113 (18)	0.0030 (2)
O2	0.0129 (2)	0.0238 (3)	0.0137 (2)	0.00159 (19)	−0.00223 (17)	−0.00001 (19)
O3	0.0216 (3)	0.0389 (4)	0.0139 (2)	−0.0011 (2)	0.0019 (2)	0.0053 (2)
N1	0.0093 (2)	0.0214 (3)	0.0119 (2)	0.00001 (19)	−0.00034 (18)	0.0004 (2)
N2	0.0103 (2)	0.0204 (3)	0.0128 (2)	0.00010 (19)	−0.00083 (18)	0.0023 (2)
N3	0.0120 (2)	0.0165 (3)	0.0126 (2)	−0.00043 (19)	0.00062 (18)	−0.00050 (19)
N4	0.0159 (3)	0.0288 (4)	0.0138 (3)	−0.0064 (2)	0.0007 (2)	0.0014 (2)
C1	0.0118 (3)	0.0194 (3)	0.0169 (3)	0.0000 (2)	0.0002 (2)	0.0015 (2)
C2	0.0124 (3)	0.0245 (4)	0.0227 (3)	0.0014 (2)	0.0026 (2)	0.0057 (3)
C3	0.0192 (3)	0.0260 (4)	0.0202 (3)	0.0055 (3)	0.0071 (3)	0.0056 (3)
C4	0.0232 (3)	0.0210 (3)	0.0150 (3)	0.0042 (3)	0.0047 (3)	0.0022 (3)
C5	0.0169 (3)	0.0183 (3)	0.0134 (3)	−0.0001 (2)	0.0008 (2)	0.0002 (2)
C6	0.0119 (3)	0.0171 (3)	0.0132 (3)	0.0001 (2)	0.0016 (2)	0.0007 (2)
C7	0.0114 (2)	0.0171 (3)	0.0136 (3)	0.0003 (2)	0.0006 (2)	0.0003 (2)
C8	0.0116 (2)	0.0170 (3)	0.0116 (3)	−0.0001 (2)	0.0009 (2)	0.0005 (2)
C9	0.0124 (3)	0.0165 (3)	0.0119 (3)	−0.0003 (2)	0.0002 (2)	−0.0008 (2)
C10	0.0145 (3)	0.0229 (3)	0.0144 (3)	0.0006 (2)	0.0006 (2)	0.0010 (2)
C11	0.0137 (3)	0.0219 (3)	0.0125 (3)	−0.0006 (2)	−0.0003 (2)	0.0008 (2)
C12	0.0169 (3)	0.0237 (4)	0.0138 (3)	−0.0005 (3)	−0.0008 (2)	0.0042 (3)
C13	0.0115 (3)	0.0256 (4)	0.0186 (3)	0.0024 (2)	−0.0004 (2)	0.0030 (3)

Geometric parameters (Å, º) top

O1—N4	1.3789 (9)	C3—C4	1.3898 (13)
O1—C10	1.4108 (10)	C3—H3A	0.993 (14)
O2—C9	1.2340 (9)	C4—C5	1.3926 (11)
O3—C10	1.2205 (9)	C4—H4A	0.992 (15)
N1—N2	1.3933 (8)	C5—C6	1.3941 (10)
N1—C9	1.4030 (9)	C5—H5A	0.978 (13)
N1—C6	1.4252 (9)	C7—C8	1.3801 (10)
N2—C7	1.3450 (9)	C7—C13	1.4821 (10)
N2—C12	1.4626 (10)	C8—C9	1.4373 (10)
N3—N4	1.3169 (9)	C10—C11	1.4113 (10)
N3—C11	1.3494 (10)	C11—H11A	0.944 (13)
N3—C8	1.4060 (9)	C12—H12A	0.939 (16)
C1—C6	1.3896 (10)	C12—H12B	0.984 (13)
C1—C2	1.3916 (11)	C12—H12C	0.964 (15)
C1—H1A	0.981 (13)	C13—H13A	0.958 (15)
C2—C3	1.3920 (13)	C13—H13B	0.993 (16)
C2—H2A	0.962 (15)	C13—H13C	0.962 (16)

N4—O1—C10	110.85 (6)	C5—C6—N1	120.48 (6)
N2—N1—C9	109.54 (5)	N2—C7—C8	107.80 (6)
N2—N1—C6	119.34 (6)	N2—C7—C13	120.80 (7)
C9—N1—C6	124.51 (6)	C8—C7—C13	131.39 (7)
C7—N2—N1	109.25 (6)	C7—C8—N3	126.63 (6)
C7—N2—C12	125.52 (6)	C7—C8—C9	110.00 (6)
N1—N2—C12	120.54 (6)	N3—C8—C9	123.32 (6)
N4—N3—C11	115.11 (6)	O2—C9—N1	124.94 (6)
N4—N3—C8	118.67 (6)	O2—C9—C8	131.77 (7)
C11—N3—C8	126.22 (6)	N1—C9—C8	103.28 (6)
N3—N4—O1	104.05 (6)	O3—C10—O1	120.01 (7)
C6—C1—C2	118.78 (7)	O3—C10—C11	135.75 (7)
C6—C1—H1A	120.5 (8)	O1—C10—C11	104.24 (6)
C2—C1—H1A	120.7 (8)	N3—C11—C10	105.74 (6)
C1—C2—C3	120.87 (7)	N3—C11—H11A	122.8 (8)
C1—C2—H2A	120.5 (9)	C10—C11—H11A	131.5 (8)
C3—C2—H2A	118.6 (9)	N2—C12—H12A	108.2 (10)
C4—C3—C2	119.75 (7)	N2—C12—H12B	110.2 (8)
C4—C3—H3A	118.7 (8)	H12A—C12—H12B	107.1 (12)
C2—C3—H3A	121.6 (9)	N2—C12—H12C	111.3 (9)
C3—C4—C5	120.08 (8)	H12A—C12—H12C	112.3 (13)
C3—C4—H4A	119.2 (9)	H12B—C12—H12C	107.6 (12)
C5—C4—H4A	120.7 (9)	C7—C13—H13A	108.6 (9)
C4—C5—C6	119.46 (7)	C7—C13—H13B	107.8 (9)
C4—C5—H5A	119.9 (8)	H13A—C13—H13B	111.8 (12)
C6—C5—H5A	120.7 (8)	C7—C13—H13C	110.5 (9)
C1—C6—C5	121.04 (7)	H13A—C13—H13C	111.3 (13)
C1—C6—N1	118.48 (7)	H13B—C13—H13C	106.8 (13)

C9—N1—N2—C7	−3.85 (9)	N2—C7—C8—N3	176.29 (7)
C6—N1—N2—C7	−156.60 (7)	C13—C7—C8—N3	−5.07 (14)
C9—N1—N2—C12	−160.86 (7)	N2—C7—C8—C9	−1.23 (9)
C6—N1—N2—C12	46.38 (10)	C13—C7—C8—C9	177.42 (8)
C11—N3—N4—O1	−1.06 (9)	N4—N3—C8—C7	−24.91 (12)
C8—N3—N4—O1	179.40 (6)	C11—N3—C8—C7	155.61 (8)
C10—O1—N4—N3	1.21 (9)	N4—N3—C8—C9	152.29 (8)
C6—C1—C2—C3	−0.73 (12)	C11—N3—C8—C9	−27.19 (12)
C1—C2—C3—C4	0.93 (13)	N2—N1—C9—O2	−176.15 (7)
C2—C3—C4—C5	−0.10 (13)	C6—N1—C9—O2	−25.12 (12)
C3—C4—C5—C6	−0.92 (12)	N2—N1—C9—C8	2.90 (8)
C2—C1—C6—C5	−0.31 (12)	C6—N1—C9—C8	153.93 (7)
C2—C1—C6—N1	−179.62 (7)	C7—C8—C9—O2	177.90 (8)
C4—C5—C6—C1	1.14 (12)	N3—C8—C9—O2	0.29 (13)
C4—C5—C6—N1	−179.58 (7)	C7—C8—C9—N1	−1.05 (8)
N2—N1—C6—C1	−152.08 (7)	N3—C8—C9—N1	−178.67 (7)
C9—N1—C6—C1	59.49 (10)	N4—O1—C10—O3	178.89 (8)
N2—N1—C6—C5	28.61 (11)	N4—O1—C10—C11	−0.94 (9)
C9—N1—C6—C5	−119.82 (8)	N4—N3—C11—C10	0.50 (10)
N1—N2—C7—C8	3.07 (9)	C8—N3—C11—C10	180.00 (7)
C12—N2—C7—C8	158.67 (7)	O3—C10—C11—N3	−179.50 (10)
N1—N2—C7—C13	−175.74 (7)	O1—C10—C11—N3	0.29 (9)
C12—N2—C7—C13	−20.15 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O3ⁱ	0.981 (14)	2.492 (13)	3.2155 (10)	130.4 (10)
C11—H11A···O2ⁱ	0.944 (13)	2.543 (13)	3.4163 (10)	153.9 (11)
C12—H12B···O2ⁱⁱ	0.984 (13)	2.369 (13)	3.3022 (10)	158.1 (11)
C13—H13A···O3ⁱⁱⁱ	0.958 (14)	2.516 (15)	3.3606 (10)	147.0 (12)

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+2, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₄O₃
M_r	272.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.6525 (3), 7.3014 (3), 15.6828 (4)
β (°)	93.982 (1)
V (Å³)	1216.83 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.56 × 0.17 × 0.08

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.941, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	44010, 6426, 4895
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.859

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.125, 1.04
No. of reflections	6426
No. of parameters	229
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.41

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O3ⁱ	0.981 (14)	2.492 (13)	3.2155 (10)	130.4 (10)
C11—H11A···O2ⁱ	0.944 (13)	2.543 (13)	3.4163 (10)	153.9 (11)
C12—H12B···O2ⁱⁱ	0.984 (13)	2.369 (13)	3.3022 (10)	158.1 (11)
C13—H13A···O3ⁱⁱⁱ	0.958 (14)	2.516 (15)	3.3606 (10)	147.0 (12)

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+2, −y+2, −z.

Footnotes

‡Thomson Reuters ResearcherID: C-7576-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship.

References

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