3-Phenyl-4H,6H-1,2,4-oxa­diazo­l-5-one

Glidewell, C.; Low, J.N.; Skakle, J.M.S.; Wardell, J.L.

doi:10.1107/S0108270104023406

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 60| Part 11| November 2004| Pages o818-o820

doi:10.1107/S0108270104023406

3-Phenyl-4H,6H-1,2,4-oxadiazol-5-one

Christopher Glidewell,^a ^* John N. Low,^b Janet M. S. Skakle ^b and James L. Wardell ^c

^aSchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, Scotland, ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and ^cInstituto de Química, Departamento de Química Inorgânica, Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro, RJ, Brazil
^*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 16 September 2004; accepted 20 September 2004; online 22 October 2004)

Molecules of the title compound, C₉H₈N₂O₂, are linked into complex sheets by a combination of N—H⋯O, C—H⋯N and C—H⋯O hydrogen bonds.

Comment

The title compound, (I) (Fig. 1), is a lactam which was obtained on the attempted recrystallization of H₂N(Ph)C=NOCH₂COOH from hot water.

The bond distances within the heterocyclic ring of (I) (Table 1) show very strong bond fixation in the C—N bonds. Thus, N2—C3 is very much shorter than C3—N4, which is rather long for its type (Allen et al., 1987 ). These values effectively preclude any electron delocalization in the N2—C3—N4 fragment. The ring puckering parameters (Cremer & Pople, 1975 ) of θ = 66.5 (2)° and φ = 335.9 (2)° for the atom sequence O1—N2—C3—N4—C5—C6 indicate a screw-boat conformation for the heterocyclic ring (Evans & Boeyens, 1989 ). The torsion angles within this ring (Table 1) indicate the near-planarity of the O1—N2—C3—N4 fragment containing the N2=C3 double bond, and of the cis-amidic fragment C3—N4—C5—C6.

The molecules of (I) are linked into a sheet of some complexity via a combination of N—H⋯O, C—H⋯O and C—H⋯N hydrogen bonds (Table 2). The formation of the sheet can most readily be analysed and described in terms of two one-dimensional substructures.

Atom N4 in the molecule at (x, y, z) acts as hydrogen-bond donor to carbonyl atom O5 in the molecule at ( $[{1 \over 2}]$ − x, $[-{1 \over 2}]$ − y, 1 − z), so generating a centrosymmetric R₂²(8) (Bernstein et al., 1995 ) dimer centred at ( $[{1 \over 4}]$ , − $[{1 \over 4}]$ , $[{1 \over 2}]$ ) (Fig. 2). The formation of this dimer is reinforced by the C—H⋯O hydrogen bond which links the same two molecules in an R₂²(14) motif, in which the R₂²(8) ring is embedded, so producing two additional rings, of R₂¹(7) type (Fig. 2).

These dimers are linked into [130] chains by one of the C—H⋯N hydrogen bonds. Aryl atom C36 in the molecule at (x, y, z) acts as donor to ring atom N2 in the molecule at (1 − x, 1 − y, 1 − z), so generating a centrosymmetric R₂²(10) motif, centred at ( $[{1 \over 2}]$ , $[{1 \over 2}]$ , $[{1 \over 2}]$ ), and linking pairs of the R₂²(8) dimers into a chain of centrosymmetric rings running parallel to the [130] direction (Fig. 2).

A second chain motif is generated by the combined action of the two C—H⋯N hydrogen bonds, which unexpectedly have the same acceptor, viz. ring atom N2. Ring atom C6 in the molecule at (x, y, z) acts as hydrogen-bond donor, via the axial atom H6A, to atom N2 in the molecule at (1 − x, −y, 1 − z), so generating a centrosymmetric R₂²(8) ring centred at ( $[{1 \over 2}]$ , 0, $[{1 \over 2}]$ ). This motif, in combination with the R₂²(10) motif, also generated by paired C—H⋯N hydrogen bonds, produces a chain of spiro-fused rings running parallel to the [010] direction (Fig. 3). The combination of the [130] and [010] chains generates an (001) sheet, but there are no direction-specific interactions between adjacent sheets.

Figure 1
The molecule of (I

), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

Figure 2
A stereoview of part of the crystal structure of (I

), showing the formation of a [130] chain of edge-fused rings. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.

Figure 3
Part of the crystal structure of (I

), showing the formation of an [010] chain of spiro-fused rings. For the sake of clarity, H atoms not involved in the motifs shown have been omitted. Atoms marked with an asterisk (*), hash (#), dollar sign ($) or ampersand (&) are at the symmetry positions (1 − x, 1 − y, 1 − z), (1 − x, −y, 1 − z) (x, 1 + y, z) and (x, y − 1, z), respectively.

Experimental

The title compound was obtained on the attempted recrystallization of H₂N(Ph)C=NOCH₂COOH (Forrester et al., 1979 ) from hot water.

Crystal data

C₉H₈N₂O₂
M_r = 176.17
Monoclinic, C2/c
a = 18.9100 (10) Å
b = 5.1093 (2) Å
c = 17.0632 (9) Å
β = 90.885 (3)°
V = 1648.40 (14) Å³
Z = 8
D_x = 1.420 Mg m⁻³
Mo Kα radiation
Cell parameters from 1903 reflections
θ = 3.2–27.6°
μ = 0.10 mm⁻¹
T = 120 (2) K
Lath, colourless
0.55 × 0.12 × 0.03 mm

Data collection

Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.954, T_max = 0.997
10 146 measured reflections
1903 independent reflections
1200 reflections with I > 2σ(I)
R_int = 0.066
θ_max = 27.6°
h = −24 → 24
k = −6 → 6
l = −20 → 22

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.136
S = 0.98
1903 reflections
118 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0779P)²] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

O1—N2	1.4320 (18)
N2—C3	1.287 (2)
C3—N4	1.396 (2)
N4—C5	1.361 (2)
C5—C6	1.493 (2)
C6—O1	1.426 (2)

O1—N2—C3—N4	3.4 (2)
N2—C3—N4—C5	21.4 (2)
C3—N4—C5—C6	−4.0 (2)
N4—C5—C6—O1	−33.9 (2)
C5—C6—O1—N2	58.6 (2)
C6—O1—N2—C3	−43.56 (19)

Table 2
Hydrogen-bonding geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O5ⁱ	0.85	2.06	2.886 (2)	165
C32—H32⋯O5ⁱ	0.95	2.39	3.296 (2)	159
C6—H6A⋯N2ⁱⁱ	0.99	2.59	3.475 (2)	148
C36—H36⋯N2ⁱⁱⁱ	0.95	2.56	3.476 (2)	161
Symmetry codes: (i) $[{\script{1\over 2}}-x,-{\script{1\over 2}}-y,1-z]$ ; (ii) 1-x,-y,1-z; (iii) 1-x,1-y,1-z.

The systematic absences permitted Cc and C2/c as possible space groups; C2/c was selected and confirmed by the subsequent structure analysis. All H atoms were located from difference maps and then treated as riding, with C—H distances of 0.95 (aromatic) or 0.99 Å (CH₂) and an N—H distance of 0.85 Å, and with U_iso(H) = 1.2U_eq(C,N).

Data collection: COLLECT (Hooft, 1999 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003 ) and SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S0108270104023406/sk1774sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270104023406/sk1774Isup2.hkl

Comment top

The title compound, (I) (Fig. 1), is a lactam, which was obtained on the attempted recrystallization of H₂N(Ph)C═NOCH₂COOH from hot water. \sch

The bond distances within the heterocyclic ring of (I) (Table 1) show very strong bond fixation in the C—N bonds. Thus, N2—C3 is very much shorter than C3—N4, which is rather long for its type (Allen et al., 1987). These values effectively preclude any electron delocalization in the N2—C3—N4 fragment. The ring puckering parameters (Cremer & Pople, 1975) of θ = 66.5 (2)° and ϕ = 335.9 (2)° for the atom-sequence O1/N2/C3/N4/C5/C6 indicate a screw-boat conformation for the heterocyclic ring (Evans & Boeyens, 1989). The torsion angles within this ring (Table 1) indicate the near-planarity of the O1—N2—C3—N4 fragment containing the N2═C3 double bond, and of the cis-amidic fragment C3—N4—C5—C6.

The molecules of (I) are linked into a sheet of some complexity via a combination of N—H···O, C—H···O and C—H···N hydrogen bonds (Table 2). The formation of the sheet can most readily be analysed and described in terms of two one-dimensional sub-structures.

Atom N4 in the molecule at (x, y, z) acts as hydrogen-bond donor to carbonyl atom O5 in the molecule at (1/2 − x, −1/2 − y, 1 − z), so generating a centrosymmetric R₂²(8) (Bernstein et al., 1995) dimer centred at (1/4, −1/4, 1/2) (Fig. 2). The formation of this dimer is reinforced by the C—H···O hydrogen bond which links the same two molecules in an R₂²(14) motif, in which the R₂²(8) ring is embedded, so producing two additional rings, of R₂¹(7) type (Fig. 2).

These dimers are linked into [130] chains by one of the C—H···N hydrogen bonds. Aryl atom C36 in the molecule at (x, y, z) acts as donor to ring atom N2 in the molecule at (1 − x, 1 − y, 1 − z), so generating a centrosymmetric R₂²(10) motif, centred at (1/2, 1/2, 1/2), and linking pairs of the R₂²(8) dimers into a chain of centrosymmetric rings running parallel to the [130] direction (Fig. 2).

A second chain motif is generated by the combined action of the two C—H···N hydrogen bonds, which unexpectedly have the same acceptor, ring atom N2. Ring atom C6 in the molecule at (x, y, z) acts as hydrogen-bond donor, via the axial atom H6A, to atom N2 in the molecule at (1 − x, −y, 1 − z), so generating a centrosymmetric R₂²(8) ring centred at (1/2, 0, 1/2). This motif, in combination with the R₂²(10) motif, also generated by paired C—H···N hydrogen bonds, produces a chain of spiro-fused rings running parallel to the [010] direction (Fig. 3). The combination of the [130] and [010] chains generates an (001) sheet, but there are no direction-specific interactions between adjacent sheets.

Experimental top

The title compound was obtained on the attempted recrystallization of H₂N(Ph)C═NOCH₂COOH (Forrester et al., 1979) from hot water.

Computing details top

Data collection: COLLECT (Hooft, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top

	Fig. 1. The molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A stereoview of part of the crystal structure of (I), showing the formation of a [130] chain of edge-fused rings. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.
	Fig. 3. Part of the crystal structure of (I), showing the formation of an [010] chain of spiro-fused rings. For the sake of clarity, H atoms not involved in the motifs shown have been omitted. Atoms marked with an asterisk (*), hash (#), dollar sign () or ampersand () are at the symmetry positions (1 − x, 1 − y, 1 − z), (1 − x, −y, 1 − z) (x, 1 + y, z) and (x, y − 1, z), respectively.

3-Phenyl-4H,6H-1,2,4-oxadiazolin-5-one top

Crystal data top

C₉H₈N₂O₂	F(000) = 736
M_r = 176.17	D_x = 1.420 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1903 reflections
a = 18.910 (1) Å	θ = 3.2–27.6°
b = 5.1093 (2) Å	µ = 0.10 mm⁻¹
c = 17.0632 (9) Å	T = 120 K
β = 90.885 (3)°	Lath, colourless
V = 1648.40 (14) Å³	0.55 × 0.12 × 0.03 mm
Z = 8

Data collection top

Nonius KappaCCD area-detector diffractometer	1903 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1200 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.6°, θ_min = 3.2°
ϕ and ω scans	h = −24→24
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −6→6
T_min = 0.954, T_max = 0.997	l = −20→22
10146 measured reflections

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0779P)²] where P = (F_o² + 2F_c²)/3
1903 reflections	(Δ/σ)_max < 0.001
118 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₉H₈N₂O₂	V = 1648.40 (14) Å³
M_r = 176.17	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 18.910 (1) Å	µ = 0.10 mm⁻¹
b = 5.1093 (2) Å	T = 120 K
c = 17.0632 (9) Å	0.55 × 0.12 × 0.03 mm
β = 90.885 (3)°

Data collection top

Nonius KappaCCD area-detector diffractometer	1903 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1200 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.997	R_int = 0.066
10146 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 0.98	Δρ_max = 0.23 e Å⁻³
1903 reflections	Δρ_min = −0.27 e Å⁻³
118 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.43308 (6)	0.1136 (2)	0.40375 (7)	0.0266 (4)
O5	0.30092 (6)	−0.3600 (2)	0.42484 (7)	0.0272 (4)
N2	0.43312 (8)	0.2398 (3)	0.47870 (9)	0.0240 (4)
N4	0.32837 (7)	−0.0004 (3)	0.49774 (8)	0.0222 (4)
C3	0.37966 (9)	0.1813 (3)	0.52107 (11)	0.0200 (4)
C5	0.34240 (9)	−0.1851 (3)	0.44265 (10)	0.0222 (4)
C6	0.41412 (9)	−0.1560 (3)	0.40829 (11)	0.0243 (5)
C31	0.37249 (9)	0.3179 (3)	0.59706 (10)	0.0207 (4)
C32	0.32239 (9)	0.2428 (4)	0.65152 (11)	0.0253 (5)
C33	0.31777 (10)	0.3726 (4)	0.72243 (11)	0.0280 (5)
C34	0.36309 (10)	0.5784 (4)	0.74019 (11)	0.0284 (5)
C35	0.41289 (10)	0.6536 (4)	0.68611 (11)	0.0272 (5)
C36	0.41785 (10)	0.5258 (3)	0.61516 (11)	0.0246 (5)
H4	0.2896	−0.0106	0.5221	0.027*
H6A	0.4493	−0.2506	0.4412	0.029*
H6B	0.4143	−0.2341	0.3552	0.029*
H32	0.2912	0.1018	0.6400	0.030*
H33	0.2833	0.3204	0.7592	0.034*
H34	0.3600	0.6668	0.7890	0.034*
H35	0.4440	0.7947	0.6979	0.033*
H36	0.4523	0.5794	0.5785	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0312 (7)	0.0264 (7)	0.0223 (7)	−0.0068 (6)	0.0039 (6)	−0.0006 (6)
O5	0.0238 (7)	0.0293 (8)	0.0286 (8)	−0.0070 (6)	0.0019 (6)	−0.0062 (6)
N2	0.0265 (9)	0.0240 (9)	0.0215 (9)	−0.0030 (7)	0.0016 (7)	−0.0024 (7)
N4	0.0175 (8)	0.0256 (9)	0.0237 (9)	−0.0035 (6)	0.0033 (7)	−0.0030 (7)
C3	0.0176 (9)	0.0181 (9)	0.0244 (10)	−0.0002 (7)	−0.0012 (8)	0.0026 (8)
C5	0.0221 (10)	0.0234 (10)	0.0209 (10)	−0.0024 (8)	−0.0011 (8)	0.0007 (8)
C6	0.0245 (10)	0.0226 (10)	0.0258 (11)	−0.0049 (8)	0.0033 (8)	−0.0034 (8)
C31	0.0201 (9)	0.0200 (10)	0.0219 (10)	0.0016 (7)	−0.0011 (8)	0.0011 (8)
C32	0.0228 (10)	0.0247 (10)	0.0284 (11)	−0.0041 (8)	−0.0011 (8)	−0.0024 (9)
C33	0.0270 (10)	0.0318 (11)	0.0254 (11)	−0.0022 (8)	0.0036 (9)	−0.0011 (9)
C34	0.0310 (11)	0.0269 (11)	0.0271 (11)	0.0025 (9)	−0.0031 (9)	−0.0062 (9)
C35	0.0277 (11)	0.0239 (10)	0.0298 (11)	−0.0047 (8)	−0.0051 (9)	−0.0043 (9)
C36	0.0232 (9)	0.0225 (10)	0.0282 (11)	−0.0019 (8)	0.0008 (8)	0.0028 (8)

Geometric parameters (Å, º) top

O1—N2	1.4320 (18)	C33—C34	1.387 (3)
N2—C3	1.287 (2)	C33—H33	0.95
C3—N4	1.396 (2)	C34—C35	1.383 (3)
N4—C5	1.361 (2)	C34—H34	0.95
C5—C6	1.493 (2)	C35—C36	1.380 (3)
C6—O1	1.426 (2)	C35—H35	0.95
C3—C31	1.481 (3)	C36—H36	0.95
C31—C32	1.391 (2)	N4—H4	0.85
C31—C36	1.397 (2)	C5—O5	1.2243 (19)
C32—C33	1.384 (3)	C6—H6A	0.99
C32—H32	0.95	C6—H6B	0.99

C6—O1—N2	112.52 (13)	C36—C35—H35	119.7
C3—N2—O1	114.05 (14)	C34—C35—H35	119.7
N2—C3—N4	122.85 (17)	C35—C36—C31	120.26 (17)
N2—C3—C31	117.77 (16)	C35—C36—H36	119.9
N4—C3—C31	119.38 (16)	C31—C36—H36	119.9
C32—C31—C36	118.96 (17)	C5—N4—C3	121.07 (15)
C32—C31—C3	121.84 (16)	C5—N4—H4	118.3
C36—C31—C3	119.19 (16)	C3—N4—H4	120.1
C33—C32—C31	120.32 (17)	O5—C5—N4	123.13 (16)
C33—C32—H32	119.8	O5—C5—C6	123.88 (16)
C31—C32—H32	119.8	N4—C5—C6	112.97 (15)
C32—C33—C34	120.48 (18)	O1—C6—C5	110.36 (14)
C32—C33—H33	119.8	O1—C6—H6A	109.6
C34—C33—H33	119.8	C5—C6—H6A	109.6
C35—C34—C33	119.31 (18)	O1—C6—H6B	109.6
C35—C34—H34	120.3	C5—C6—H6B	109.6
C33—C34—H34	120.3	H6A—C6—H6B	108.1
C36—C35—C34	120.67 (17)

O1—N2—C3—N4	3.4 (2)	C3—C31—C32—C33	179.12 (16)
N2—C3—N4—C5	21.4 (2)	C31—C32—C33—C34	−0.2 (3)
C3—N4—C5—C6	−4.0 (2)	C32—C33—C34—C35	0.3 (3)
N4—C5—C6—O1	−33.9 (2)	C33—C34—C35—C36	−0.1 (3)
C5—C6—O1—N2	58.6 (2)	C34—C35—C36—C31	0.0 (3)
C6—O1—N2—C3	−43.56 (19)	C32—C31—C36—C35	0.1 (3)
O1—N2—C3—C31	−175.50 (13)	C3—C31—C36—C35	−179.03 (16)
N2—C3—C31—C32	−170.97 (16)	C31—C3—N4—C5	−159.71 (15)
N4—C3—C31—C32	10.1 (2)	C3—N4—C5—O5	174.28 (15)
N2—C3—C31—C36	8.2 (2)	N2—O1—C6—C5	58.59 (19)
N4—C3—C31—C36	−170.81 (15)	O5—C5—C6—O1	147.78 (16)
C36—C31—C32—C33	0.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O5ⁱ	0.85	2.06	2.886 (2)	165
C32—H32···O5ⁱ	0.95	2.39	3.296 (2)	159
C6—H6A···N2ⁱⁱ	0.99	2.59	3.475 (2)	148
C36—H36···N2ⁱⁱⁱ	0.95	2.56	3.476 (2)	161

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

Experimental details

Crystal data
Chemical formula	C₉H₈N₂O₂
M_r	176.17
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	120
a, b, c (Å)	18.910 (1), 5.1093 (2), 17.0632 (9)
β (°)	90.885 (3)
V (Å³)	1648.40 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.55 × 0.12 × 0.03

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.954, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	10146, 1903, 1200
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.136, 0.98
No. of reflections	1903
No. of parameters	118
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.27

Computer programs: COLLECT (Hooft, 1999), DENZO (Otwinowski & Minor, 1997) and COLLECT, DENZO and COLLECT, OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top

O1—N2	1.4320 (18)	N4—C5	1.361 (2)
N2—C3	1.287 (2)	C5—C6	1.493 (2)
C3—N4	1.396 (2)	C6—O1	1.426 (2)

O1—N2—C3—N4	3.4 (2)	N4—C5—C6—O1	−33.9 (2)
N2—C3—N4—C5	21.4 (2)	C5—C6—O1—N2	58.6 (2)
C3—N4—C5—C6	−4.0 (2)	C6—O1—N2—C3	−43.56 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O5ⁱ	0.85	2.06	2.886 (2)	165
C32—H32···O5ⁱ	0.95	2.39	3.296 (2)	159
C6—H6A···N2ⁱⁱ	0.99	2.59	3.475 (2)	148
C36—H36···N2ⁱⁱⁱ	0.95	2.56	3.476 (2)	161

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

Acknowledgements

The X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England; the authors thank the staff for all their help and advice. JNL thanks NCR Self-Service, Dundee, for grants which have provided computing facilities for this work. JLW thanks CNPq and FAPERJ for financial support.

References

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Volume 60| Part 11| November 2004| Pages o818-o820

doi:10.1107/S0108270104023406

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

3-Phenyl-4H,6H-1,2,4-oxa­diazo­l-5-one

Comment

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-Phenyl-4H,6H-1,2,4-oxadiazol-5-one