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

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], C(13)H(12)N(4)O(3), the oxadiazole and pyrazole rings are essentially planar [maximum deviations = 0.006 (1) and 0.019 (1) Å, respectively] and are inclined at inter-planar angles of 37.84 (4) and 46.60 (4)°, respectively, with respect to the benzene ring. In the crystal, adjacent mol-ecules are inter-connected into a three-dimensional supra-molecular network via inter-molecular C-H⋯O hydrogen bonds. Weak inter-molecular π-π aromatic stacking inter-actions [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. (2009 ▶, 2010 ▶). 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 = 272.27

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.125

S = 1.04

6426 reflections

229 parameters

All H-atom parameters refined

Δρmax = 0.55 e Å−3

Δρmin = −0.41 e Å−3

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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015667/sj2767Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H12N4O3	F(000) = 568
Mr = 272.27	Dx = 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

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

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(Fo2) + (0.0663P)2 + 0.1919P] where P = (Fo2 + 2Fc2)/3
6426 reflections	(Δ/σ)max = 0.001
229 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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) ; (ii) ; (iii) .