3-{5-Bromo-2-[(tri­phenyl­phosphanyl­idene)amino]­phen­yl}-4,5-di­hydro-1,2,3-oxa­diazol-3-ylium-5-olate

Grossie, D.; Harrison, L.; Turnbull, K.

doi:10.1107/S1600536813017765

organic compounds

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Volume 69| Part 8| August 2013| Page o1196

doi:10.1107/S1600536813017765

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3-{5-Bromo-2-[(triphenylphosphanylidene)amino]phenyl}-4,5-dihydro-1,2,3-oxadiazol-3-ylium-5-olate

David Grossie,^a ^* Leanna Harrison ^a and Kenneth Turnbull ^a

^aDepartment of Chemistry, Wright State University, Dayton, OH 45435, USA
^*Correspondence e-mail: david.grossie@wright.edu

(Received 24 June 2013; accepted 27 June 2013; online 3 July 2013)

In general, sydnone compounds are synthesized with an aromatic substituent at the N-3 position and this feature adds to the stability of the mesoionic five-membered heterocyclic ring. In the title compound, C₂₆H₁₉BrN₃O₂P, the aromatic substitutent is triphenylphosphine 4-bromophenylimide. The dihedral angle between the planes of the sydnone and the attached phenyl ring is 45.98 (7)°. In the crystal, the molecules packed as pairs in which the sydnone rings lie in parallel planes separated by 0.849 Å and sandwiched between two parallel phenyl rings. The molecules interact through cyclic C—H⋯O=C hydrogen bonds.

Related literature

For more information on the sydnone family of compounds, see: Ohta & Kato (1969 ). For their synthesis and structures, see: Grossie & Turnbull (1992 ); Grossie et al. (2001 , 2007 ); Hope & Thiessen (1969 ); Hodson & Turnbull (1985 ); Ollis & Ramsden (1976 ); Riddle et al. (2004a ,b ,c ).

Experimental

Crystal data

C₂₆H₁₉BrN₃O₂P
M_r = 516.33
Monoclinic, P 2₁ /n
a = 7.5207 (8) Å
b = 13.8672 (15) Å
c = 21.816 (2) Å
β = 95.449 (2)°
V = 2264.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.92 mm⁻¹
T = 173 K
0.43 × 0.30 × 0.28 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Siemens, 1996 ) T_min = 0.50, T_max = 0.58
46513 measured reflections
6964 independent reflections
5914 reflections with I > 2.0σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.074
S = 0.92
6964 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H41⋯O5ⁱ	0.91	2.48	3.344 (2)	159
C72—H721⋯O5ⁱ	0.94	2.37	3.297 (2)	173
Symmetry code: (i) -x+2, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ); molecular graphics: CAMERON (Watkin et al., 1996 ); software used to prepare material for publication: CRYSTALS.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813017765/gg2120sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813017765/gg2120Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813017765/gg2120Isup3.cml

checkCIF report

Comment top

In the title compound the bond distances and angles are within the expected ranges. The sydnone ring (O1– C5) and the phenyl ring (C31 – C36) in the structure are planar, all deviations from the mean plane being less than 0.1 Å. The angle between the planes of the sydnone and the attached phenyl ring is 45.98°. The phenyl ring containing the bromine is stacked through the unit cell in a herringbone pattern in the b direction of the unit cell with slippage in the stack of 4.466 Å. The molecules are oriented in an alternating pattern in these herringbone stacks. The analysis of short ring interactions shows a distance between the sydnone and the phenyl ring (C31 – C36) in a symmetry related molecule as 5.8852 (1) Å. A H - π-ring interaction between C(33) and H(331) has a distance of 2.68 Å. The analysis of the X—Y Cg(Pi-Ring) interactions show that the interaction between the sydnone ring and Br(35) have a X···Cg of 3.9267 Å. The bromine atom shows flattening in the direction of the bond to C(35). The analysis of short intra and inter-molecular forces reveals multiple contacts within the structure, two of which have parameters suggestive of hydrogen bonding.

Related literature top

For more information on the sydnone family of compounds, see: Ohta & Kato (1969). For their synthesis and structures, see: Grossie & Turnbull (1992); Grossie et al. (2001, 2007); Hope & Thiessen (1969); Hodson & Turnbull (1985); Ollis & Ramsden (1976); Riddle et al. (2004a,b,c).

Experimental top

Triphenylphosphine-2-(4-bromo-3-sydnonyl)phenyl imide was prepared from 3-(2-amino-5-bromophenyl)sydnone with an 85% yield via a Mitsunobu process involving treatment with triphenylphosphine (1.1 eq) then diisopropyl azodicarboxylate (1.1 eq) in dry tetrahydrofuran at room temperature for 4 h.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures top

Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.

3-{5-Bromo-2-[(triphenylphosphanylidene)amino]phenyl}-4,5-dihydro-1,2,3-oxadiazol-3-ylium-5-olate top

Crystal data top

C₂₆H₁₉BrN₃O₂P	F(000) = 1048
M_r = 516.33	D_x = 1.514 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8702 reflections
a = 7.5207 (8) Å	θ = 5–60°
b = 13.8672 (15) Å	µ = 1.92 mm⁻¹
c = 21.816 (2) Å	T = 173 K
β = 95.449 (2)°	Block, yellow
V = 2264.9 (4) Å³	0.43 × 0.30 × 0.28 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	5914 reflections with I > 2.0σ(I)
Graphite monochromator	R_int = 0.029
ω scans	θ_max = 31.3°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −10→10
T_min = 0.50, T_max = 0.58	k = −19→19
46513 measured reflections	l = −30→30
6964 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.074	Method = Modified Sheldrick w = 1/[σ²(F²) + ( 0.04P)² + 1.42P] , where P = (max(F_o²,0) + 2F_c²)/3
S = 0.92	(Δ/σ)_max = 0.002
6964 reflections	Δρ_max = 0.86 e Å⁻³
298 parameters	Δρ_min = −0.48 e Å⁻³
0 restraints

Crystal data top

C₂₆H₁₉BrN₃O₂P	V = 2264.9 (4) Å³
M_r = 516.33	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.5207 (8) Å	µ = 1.92 mm⁻¹
b = 13.8672 (15) Å	T = 173 K
c = 21.816 (2) Å	0.43 × 0.30 × 0.28 mm
β = 95.449 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	6964 independent reflections
Absorption correction: multi-scan (SADABS; Siemens, 1996)	5914 reflections with I > 2.0σ(I)
T_min = 0.50, T_max = 0.58	R_int = 0.029
46513 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 0.92	Δρ_max = 0.86 e Å⁻³
6964 reflections	Δρ_min = −0.48 e Å⁻³
298 parameters

Special details top

Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

Sydnone ring

0.7299 (5) x - 0.6166 (6) y + 0.2950 (7) z = -0.190 (11)

* -0.006 (1) O1 * 0.004 (1) N2 * 0.001 (1) N3 * -0.007 (1) C4 * 0.008 (1) C5

Phenyl ring at N(3)

-0.4830 (5) x + 0.7617 (4) y + 0.4318 (5) z = 10.247 (6)

* -0.007 (1) C31 * 0.003 (1) C32 * 0.004 (1) C33 * -0.008 (1) C34 * 0.004 (1) C35 * 0.004 (1) C36 * 0.066 (1) Br35

Angle to previous plane (with approximate e.s.d.) = 45.99 (7)

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

	x	y	z	U_iso*/U_eq
Br35	0.226245 (18)	0.622503 (11)	0.439272 (7)	0.0272
C35	0.45423 (17)	0.65812 (10)	0.47685 (6)	0.0192
C36	0.55726 (17)	0.72268 (9)	0.44721 (6)	0.0179
C31	0.72208 (16)	0.74960 (9)	0.47645 (6)	0.0159
N3	0.83407 (14)	0.81101 (8)	0.44354 (5)	0.0172
C4	0.93052 (19)	0.88673 (10)	0.46540 (7)	0.0209
C5	1.02656 (19)	0.91890 (10)	0.41683 (7)	0.0233
O5	1.13573 (15)	0.98178 (8)	0.41029 (6)	0.0315
O1	0.97050 (15)	0.85637 (8)	0.36779 (5)	0.0261
N2	0.85054 (17)	0.78868 (9)	0.38551 (6)	0.0231
C32	0.78948 (17)	0.71586 (9)	0.53535 (6)	0.0165
N37	0.95384 (15)	0.74604 (8)	0.55906 (5)	0.0194
P38	1.05534 (4)	0.74521 (2)	0.625347 (15)	0.0158
C81	1.21291 (17)	0.84316 (9)	0.62612 (6)	0.0177
C82	1.22728 (19)	0.91448 (11)	0.67099 (7)	0.0248
C83	1.3422 (2)	0.99241 (12)	0.66550 (8)	0.0301
C84	1.44642 (19)	0.99724 (11)	0.61692 (8)	0.0290
C85	1.4353 (2)	0.92545 (11)	0.57256 (8)	0.0280
C86	1.3175 (2)	0.84922 (10)	0.57645 (7)	0.0238
C61	1.18310 (17)	0.63657 (9)	0.64233 (6)	0.0180
C62	1.12610 (18)	0.55137 (10)	0.61256 (7)	0.0223
C63	1.2185 (2)	0.46591 (11)	0.62551 (8)	0.0264
C64	1.3693 (2)	0.46523 (11)	0.66730 (7)	0.0265
C65	1.4274 (2)	0.54983 (11)	0.69687 (7)	0.0263
C66	1.33492 (19)	0.63547 (10)	0.68462 (7)	0.0227
C71	0.91867 (17)	0.76109 (10)	0.68830 (6)	0.0179
C72	0.81337 (19)	0.84392 (10)	0.68936 (7)	0.0225
C73	0.6995 (2)	0.85532 (11)	0.73560 (7)	0.0260
C74	0.68674 (19)	0.78413 (11)	0.77958 (6)	0.0247
C75	0.7890 (2)	0.70123 (12)	0.77832 (7)	0.0272
C76	0.90552 (19)	0.68980 (11)	0.73294 (7)	0.0244
C33	0.67735 (17)	0.65022 (10)	0.56305 (6)	0.0190
C34	0.51400 (18)	0.62114 (10)	0.53432 (6)	0.0196
H361	0.5190	0.7485	0.4081	0.0233*
H41	0.9287	0.9095	0.5044	0.0256*
H821	1.1602	0.9097	0.7057	0.0301*
H831	1.3474	1.0416	0.6953	0.0364*
H841	1.5233	1.0489	0.6139	0.0343*
H851	1.5054	0.9288	0.5384	0.0345*
H861	1.3078	0.8016	0.5461	0.0291*
H621	1.0273	0.5523	0.5829	0.0268*
H631	1.1804	0.4086	0.6056	0.0317*
H641	1.4308	0.4073	0.6754	0.0314*
H651	1.5269	0.5494	0.7255	0.0320*
H661	1.3731	0.6927	0.7041	0.0277*
H721	0.8187	0.8918	0.6593	0.0263*
H731	0.6310	0.9122	0.7360	0.0311*
H741	0.6102	0.7900	0.8110	0.0298*
H751	0.7780	0.6529	0.8082	0.0338*
H761	0.9720	0.6334	0.7326	0.0299*
H331	0.7152	0.6245	0.6017	0.0224*
H341	0.4431	0.5785	0.5532	0.0248*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br35	0.01877 (7)	0.03313 (9)	0.02875 (8)	−0.00838 (5)	−0.00334 (5)	0.00226 (6)
C35	0.0152 (5)	0.0202 (6)	0.0220 (6)	−0.0033 (5)	0.0010 (4)	−0.0017 (5)
C36	0.0188 (6)	0.0182 (6)	0.0167 (5)	−0.0006 (5)	0.0014 (4)	−0.0003 (4)
C31	0.0170 (5)	0.0150 (5)	0.0164 (5)	−0.0023 (4)	0.0045 (4)	0.0006 (4)
N3	0.0173 (5)	0.0171 (5)	0.0175 (5)	−0.0011 (4)	0.0037 (4)	0.0016 (4)
C4	0.0226 (6)	0.0191 (6)	0.0212 (6)	−0.0050 (5)	0.0028 (5)	0.0023 (5)
C5	0.0210 (6)	0.0209 (6)	0.0287 (7)	0.0002 (5)	0.0049 (5)	0.0058 (5)
O5	0.0266 (5)	0.0285 (5)	0.0405 (6)	−0.0077 (4)	0.0084 (5)	0.0106 (5)
O1	0.0312 (5)	0.0226 (5)	0.0267 (5)	−0.0022 (4)	0.0148 (4)	0.0027 (4)
N2	0.0294 (6)	0.0205 (5)	0.0209 (5)	−0.0027 (5)	0.0105 (5)	0.0004 (4)
C32	0.0162 (5)	0.0166 (5)	0.0169 (5)	−0.0007 (4)	0.0029 (4)	−0.0007 (4)
N37	0.0173 (5)	0.0234 (5)	0.0171 (5)	−0.0047 (4)	0.0003 (4)	0.0017 (4)
P38	0.01456 (14)	0.01639 (14)	0.01647 (14)	−0.00207 (11)	0.00152 (11)	0.00093 (11)
C81	0.0151 (5)	0.0163 (5)	0.0213 (6)	−0.0010 (4)	0.0002 (4)	0.0015 (5)
C82	0.0191 (6)	0.0284 (7)	0.0265 (7)	−0.0044 (5)	0.0006 (5)	−0.0063 (6)
C83	0.0233 (6)	0.0269 (7)	0.0391 (8)	−0.0062 (6)	−0.0033 (6)	−0.0099 (6)
C84	0.0191 (6)	0.0218 (7)	0.0453 (9)	−0.0060 (5)	−0.0017 (6)	0.0023 (6)
C85	0.0242 (7)	0.0246 (7)	0.0365 (8)	−0.0034 (5)	0.0093 (6)	0.0052 (6)
C86	0.0256 (6)	0.0196 (6)	0.0272 (7)	−0.0030 (5)	0.0082 (5)	−0.0005 (5)
C61	0.0169 (5)	0.0172 (6)	0.0204 (6)	−0.0010 (4)	0.0040 (5)	0.0010 (4)
C62	0.0180 (6)	0.0210 (6)	0.0281 (7)	−0.0034 (5)	0.0036 (5)	−0.0023 (5)
C63	0.0236 (6)	0.0191 (6)	0.0376 (8)	−0.0019 (5)	0.0079 (6)	−0.0024 (6)
C64	0.0262 (7)	0.0224 (6)	0.0321 (7)	0.0054 (5)	0.0086 (6)	0.0054 (6)
C65	0.0247 (7)	0.0284 (7)	0.0254 (7)	0.0044 (6)	0.0001 (5)	0.0036 (5)
C66	0.0232 (6)	0.0219 (6)	0.0224 (6)	−0.0007 (5)	−0.0008 (5)	0.0003 (5)
C71	0.0159 (5)	0.0214 (6)	0.0164 (5)	−0.0024 (4)	0.0008 (4)	0.0010 (5)
C72	0.0211 (6)	0.0226 (6)	0.0243 (6)	0.0001 (5)	0.0051 (5)	0.0038 (5)
C73	0.0229 (6)	0.0262 (7)	0.0298 (7)	0.0025 (5)	0.0076 (6)	0.0006 (6)
C74	0.0209 (6)	0.0342 (7)	0.0194 (6)	−0.0022 (5)	0.0046 (5)	−0.0010 (5)
C75	0.0269 (7)	0.0349 (8)	0.0202 (6)	0.0010 (6)	0.0049 (5)	0.0086 (6)
C76	0.0239 (6)	0.0266 (7)	0.0231 (7)	0.0049 (5)	0.0046 (5)	0.0069 (5)
C33	0.0180 (6)	0.0205 (6)	0.0185 (6)	−0.0013 (5)	0.0024 (5)	0.0029 (5)
C34	0.0177 (6)	0.0195 (6)	0.0221 (6)	−0.0035 (5)	0.0043 (5)	0.0013 (5)

Geometric parameters (Å, º) top

Br35—C35	1.8945 (13)	C85—C86	1.387 (2)
C35—C36	1.3838 (18)	C85—H851	0.954
C35—C34	1.3892 (19)	C86—H861	0.934
C36—C31	1.3902 (17)	C61—C62	1.3959 (19)
C36—H361	0.945	C61—C66	1.3983 (19)
C31—N3	1.4371 (16)	C62—C63	1.389 (2)
C31—C32	1.4154 (17)	C62—H621	0.938
N3—C4	1.3381 (17)	C63—C64	1.386 (2)
N3—N2	1.3206 (16)	C63—H631	0.938
C4—C5	1.4101 (19)	C64—C65	1.389 (2)
C4—H41	0.908	C64—H641	0.935
C5—O5	1.2154 (17)	C65—C66	1.389 (2)
C5—O1	1.4101 (19)	C65—H651	0.928
O1—N2	1.3822 (15)	C66—H661	0.932
C32—N37	1.3598 (16)	C71—C72	1.3966 (19)
C32—C33	1.4148 (18)	C71—C76	1.3978 (18)
N37—P38	1.5698 (12)	C72—C73	1.393 (2)
P38—C81	1.8016 (13)	C72—H721	0.936
P38—C61	1.8062 (13)	C73—C74	1.386 (2)
P38—C71	1.8053 (13)	C73—H731	0.943
C81—C82	1.3885 (19)	C74—C75	1.385 (2)
C81—C86	1.4006 (19)	C74—H741	0.939
C82—C83	1.396 (2)	C75—C76	1.392 (2)
C82—H821	0.951	C75—H751	0.944
C83—C84	1.378 (2)	C76—H761	0.929
C83—H831	0.941	C33—C34	1.3850 (18)
C84—C85	1.385 (2)	C33—H331	0.935
C84—H841	0.927	C34—H341	0.920

Br35—C35—C36	119.37 (10)	C81—C86—C85	120.13 (14)
Br35—C35—C34	119.76 (10)	C81—C86—H861	119.7
C36—C35—C34	120.86 (12)	C85—C86—H861	120.2
C35—C36—C31	118.28 (12)	P38—C61—C62	118.47 (10)
C35—C36—H361	122.1	P38—C61—C66	121.98 (10)
C31—C36—H361	119.6	C62—C61—C66	119.55 (12)
C36—C31—N3	117.99 (11)	C61—C62—C63	120.13 (13)
C36—C31—C32	123.69 (11)	C61—C62—H621	119.9
N3—C31—C32	118.24 (11)	C63—C62—H621	120.0
C31—N3—C4	127.63 (11)	C62—C63—C64	120.12 (14)
C31—N3—N2	116.92 (11)	C62—C63—H631	120.3
C4—N3—N2	115.38 (11)	C64—C63—H631	119.6
N3—C4—C5	106.23 (12)	C63—C64—C65	120.08 (14)
N3—C4—H41	123.4	C63—C64—H641	119.3
C5—C4—H41	130.4	C65—C64—H641	120.6
C4—C5—O5	135.64 (15)	C64—C65—C66	120.20 (14)
C4—C5—O1	103.76 (11)	C64—C65—H651	120.3
O5—C5—O1	120.59 (13)	C66—C65—H651	119.5
C5—O1—N2	111.20 (10)	C61—C66—C65	119.92 (13)
O1—N2—N3	103.40 (11)	C61—C66—H661	119.2
C31—C32—N37	118.55 (11)	C65—C66—H661	120.8
C31—C32—C33	115.07 (11)	P38—C71—C72	118.53 (10)
N37—C32—C33	126.35 (12)	P38—C71—C76	121.79 (10)
C32—N37—P38	133.88 (10)	C72—C71—C76	119.49 (12)
N37—P38—C81	105.37 (6)	C71—C72—C73	119.60 (13)
N37—P38—C61	113.44 (6)	C71—C72—H721	120.7
C81—P38—C61	106.88 (6)	C73—C72—H721	119.7
N37—P38—C71	115.95 (6)	C72—C73—C74	120.53 (14)
C81—P38—C71	108.81 (6)	C72—C73—H731	118.4
C61—P38—C71	106.02 (6)	C74—C73—H731	121.0
P38—C81—C82	123.42 (10)	C73—C74—C75	120.17 (13)
P38—C81—C86	117.07 (10)	C73—C74—H741	122.0
C82—C81—C86	119.40 (12)	C75—C74—H741	117.8
C81—C82—C83	119.89 (14)	C74—C75—C76	119.79 (13)
C81—C82—H821	120.0	C74—C75—H751	119.4
C83—C82—H821	120.1	C76—C75—H751	120.8
C82—C83—C84	120.36 (14)	C71—C76—C75	120.40 (13)
C82—C83—H831	119.2	C71—C76—H761	121.1
C84—C83—H831	120.5	C75—C76—H761	118.5
C83—C84—C85	120.07 (14)	C32—C33—C34	122.22 (12)
C83—C84—H841	119.7	C32—C33—H331	119.2
C85—C84—H841	120.2	C34—C33—H331	118.6
C84—C85—C86	120.10 (14)	C35—C34—C33	119.87 (12)
C84—C85—H851	120.6	C35—C34—H341	119.4
C86—C85—H851	119.3	C33—C34—H341	120.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H41···O5ⁱ	0.91	2.48	3.344 (2)	159
C72—H721···O5ⁱ	0.94	2.37	3.297 (2)	173

Symmetry code: (i) −x+2, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₆H₁₉BrN₃O₂P
M_r	516.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	7.5207 (8), 13.8672 (15), 21.816 (2)
β (°)	95.449 (2)
V (Å³)	2264.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.92
Crystal size (mm)	0.43 × 0.30 × 0.28

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Siemens, 1996)
T_min, T_max	0.50, 0.58
No. of measured, independent and observed [I > 2.0σ(I)] reflections	46513, 6964, 5914
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.730

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.074, 0.92
No. of reflections	6964
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.48

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), CAMERON (Watkin et al., 1996).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H41···O5ⁱ	0.91	2.48	3.344 (2)	159
C72—H721···O5ⁱ	0.94	2.37	3.297 (2)	173

Symmetry code: (i) −x+2, −y+2, −z+1.

Acknowledgements

The authors would like to acknowledge the diffractometer time granted by A. Hunter, Youngstown State University

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
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Riddle, G. B., Grossie, D. A. & Turnbull, K. (2004a). Acta Cryst. E60, o977–o978. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-{5-Bromo-2-[(tri­phenyl­phosphanyl­­idene)amino]­phen­yl}-4,5-di­hydro-1,2,3-oxa­diazol-3-ylium-5-olate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-{5-Bromo-2-[(triphenylphosphanylidene)amino]phenyl}-4,5-dihydro-1,2,3-oxadiazol-3-ylium-5-olate