2-Bromo-3-phenyl-1-(3-phenyl-sydnon-4-yl)prop-2-en-1-one.

THE TITLE SYDNONE DERIVATIVE [SYSTEMATIC NAME: 2-bromo-1-(5-oxido-3-phenyl-1,2,3-oxadiazo-lium-4-yl)-3-phenyl-prop-2-en-1-one], C(17)H(11)BrN(2)O(3), exists in a Z configuration with respect to the acyclic C=C bond. An intra-molecular C-H⋯Br hydrogen bond generates a six-membered ring, producing an S(6) ring motif. The 1,2,3-oxadiazole ring in the sydnone unit is essentially planar [maximum deviation = 0.011 (2) Å] and forms dihedral angles of 55.39 (13) and 57.12 (12)° with the two benzene rings. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link mol-ecules into two-mol-ecule-thick arrays parallel to the bc plane. The crystal structure also features a short inter-molecular N⋯C contacts [3.030 (3) Å] as well as C-H⋯π and π-π inter-actions [centroid-centroid distances = 3.3798 (11) and 3.2403 (12) Å].

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 related structures, see: Baker & Ollis (1957 ▶); Goh et al. (2010 ▶); Grossie et al. (2009 ▶). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C17H11BrN2O3

M = 371.19

Monoclinic,

a = 15.0512 (5) Å

b = 5.9887 (2) Å

c = 22.3940 (6) Å

β = 129.444 (2)°

V = 1558.80 (8) Å3

Z = 4

Mo Kα radiation

μ = 2.65 mm−1

T = 293 K

0.38 × 0.27 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.435, T max = 0.658

18185 measured reflections

4816 independent reflections

3232 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.103

S = 1.02

4816 reflections

252 parameters

All H-atom parameters refined

Δρmax = 0.64 e Å−3

Δρmin = −0.83 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/S1600536810015205/tk2656sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015205/tk2656Isup2.hkl

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

C17H11BrN2O3	F(000) = 744
Mr = 371.19	Dx = 1.582 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4335 reflections
a = 15.0512 (5) Å	θ = 2.4–29.8°
b = 5.9887 (2) Å	µ = 2.65 mm−1
c = 22.3940 (6) Å	T = 293 K
β = 129.444 (2)°	Block, yellow
V = 1558.80 (8) Å3	0.38 × 0.27 × 0.17 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	4816 independent reflections
Radiation source: fine-focus sealed tube	3232 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 30.6°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→21
Tmin = 0.435, Tmax = 0.658	k = −8→8
18185 measured reflections	l = −32→29

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	All H-atom parameters refined
S = 1.02	w = 1/[σ2(Fo2) + (0.043P)2 + 0.6594P] where P = (Fo2 + 2Fc2)/3
4816 reflections	(Δ/σ)max = 0.001
252 parameters	Δρmax = 0.64 e Å−3
0 restraints	Δρmin = −0.83 e Å−3

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
Br1	0.90010 (2)	0.71291 (5)	0.499676 (17)	0.06462 (12)
O1	0.50418 (13)	0.7541 (2)	0.52358 (8)	0.0376 (3)
O2	0.69784 (14)	0.7260 (2)	0.61954 (8)	0.0452 (4)
O3	0.66790 (15)	0.8945 (4)	0.42133 (10)	0.0688 (5)
N1	0.49069 (14)	0.7454 (2)	0.42344 (9)	0.0320 (3)
N2	0.42695 (15)	0.7565 (3)	0.44402 (10)	0.0370 (4)
C1	0.4535 (2)	0.5529 (4)	0.31430 (14)	0.0492 (5)
C2	0.3975 (2)	0.5418 (5)	0.23612 (15)	0.0590 (7)
C3	0.3218 (2)	0.7063 (5)	0.18686 (14)	0.0584 (7)
C4	0.3014 (2)	0.8844 (5)	0.21526 (14)	0.0603 (7)
C5	0.3563 (2)	0.9003 (4)	0.29352 (13)	0.0485 (5)
C6	0.43174 (17)	0.7337 (3)	0.34129 (11)	0.0364 (4)
C7	0.61978 (17)	0.7329 (3)	0.55169 (12)	0.0345 (4)
C8	0.60568 (16)	0.7289 (3)	0.48251 (11)	0.0331 (4)
C9	0.68943 (17)	0.7596 (3)	0.46933 (12)	0.0394 (4)
C10	0.79547 (16)	0.6228 (4)	0.51474 (11)	0.0379 (4)
C11	0.80979 (17)	0.4513 (4)	0.55817 (12)	0.0387 (4)
C12	0.90186 (17)	0.2897 (3)	0.60789 (12)	0.0399 (4)
C13	0.87661 (19)	0.1127 (4)	0.63547 (13)	0.0437 (5)
C14	0.9577 (2)	−0.0474 (4)	0.68386 (14)	0.0520 (6)
C15	1.0664 (2)	−0.0325 (5)	0.70620 (16)	0.0600 (7)
C16	1.0933 (2)	0.1406 (5)	0.68038 (19)	0.0679 (8)
C17	1.0137 (2)	0.3022 (5)	0.63199 (17)	0.0588 (7)
H1A	0.505 (2)	0.445 (4)	0.3489 (14)	0.054 (7)*
H2A	0.411 (2)	0.426 (5)	0.2196 (16)	0.065 (8)*
H3A	0.286 (2)	0.695 (4)	0.1345 (17)	0.059 (8)*
H4A	0.251 (2)	0.995 (5)	0.1826 (16)	0.072 (9)*
H5A	0.343 (2)	1.015 (4)	0.3145 (14)	0.053 (7)*
H11A	0.7463 (18)	0.430 (4)	0.5558 (12)	0.039 (6)*
H13A	0.802 (2)	0.111 (4)	0.6204 (13)	0.045 (6)*
H14A	0.937 (2)	−0.169 (5)	0.7008 (16)	0.064 (8)*
H15A	1.122 (3)	−0.135 (5)	0.7404 (17)	0.074 (9)*
H16A	1.167 (3)	0.148 (6)	0.6941 (19)	0.086 (10)*
H17A	1.034 (2)	0.422 (5)	0.6138 (16)	0.073 (9)*

	U11	U22	U33	U12	U13	U23
Br1	0.05352 (16)	0.0904 (2)	0.0739 (2)	0.00434 (13)	0.05173 (15)	0.01659 (14)
O1	0.0456 (8)	0.0357 (7)	0.0432 (8)	0.0004 (6)	0.0337 (7)	−0.0005 (6)
O2	0.0507 (9)	0.0494 (9)	0.0344 (7)	0.0007 (7)	0.0265 (7)	0.0009 (6)
O3	0.0518 (9)	0.0982 (14)	0.0619 (11)	0.0083 (10)	0.0387 (9)	0.0395 (10)
N1	0.0357 (8)	0.0292 (8)	0.0359 (8)	0.0006 (6)	0.0250 (7)	−0.0002 (6)
N2	0.0399 (8)	0.0339 (8)	0.0432 (9)	0.0009 (6)	0.0293 (8)	−0.0012 (7)
C1	0.0559 (13)	0.0462 (12)	0.0469 (12)	0.0092 (11)	0.0333 (11)	−0.0010 (10)
C2	0.0718 (17)	0.0574 (15)	0.0522 (14)	0.0037 (13)	0.0415 (13)	−0.0145 (12)
C3	0.0565 (14)	0.0771 (18)	0.0352 (12)	0.0021 (13)	0.0261 (11)	−0.0098 (12)
C4	0.0563 (14)	0.0746 (18)	0.0367 (12)	0.0199 (13)	0.0233 (11)	0.0045 (12)
C5	0.0504 (12)	0.0527 (13)	0.0381 (11)	0.0135 (10)	0.0261 (10)	−0.0010 (10)
C6	0.0348 (9)	0.0411 (10)	0.0335 (9)	−0.0005 (8)	0.0218 (8)	−0.0036 (8)
C7	0.0411 (10)	0.0282 (9)	0.0401 (10)	−0.0015 (7)	0.0285 (9)	0.0002 (8)
C8	0.0350 (9)	0.0327 (9)	0.0340 (9)	0.0010 (7)	0.0230 (8)	0.0024 (7)
C9	0.0378 (10)	0.0495 (12)	0.0352 (10)	−0.0033 (8)	0.0252 (9)	0.0032 (9)
C10	0.0345 (9)	0.0492 (11)	0.0377 (10)	−0.0044 (8)	0.0265 (8)	−0.0041 (9)
C11	0.0329 (9)	0.0438 (11)	0.0432 (11)	−0.0032 (8)	0.0259 (9)	−0.0038 (9)
C12	0.0344 (9)	0.0425 (11)	0.0439 (11)	−0.0014 (8)	0.0254 (9)	−0.0038 (9)
C13	0.0373 (10)	0.0471 (12)	0.0443 (11)	−0.0038 (9)	0.0247 (9)	−0.0031 (9)
C14	0.0500 (13)	0.0471 (13)	0.0534 (13)	0.0009 (10)	0.0302 (11)	0.0039 (11)
C15	0.0490 (13)	0.0571 (15)	0.0614 (15)	0.0134 (12)	0.0291 (12)	0.0067 (12)
C16	0.0410 (13)	0.0770 (19)	0.083 (2)	0.0117 (12)	0.0384 (14)	0.0138 (15)
C17	0.0417 (12)	0.0630 (15)	0.0771 (18)	0.0039 (11)	0.0402 (13)	0.0134 (14)

Br1—C10	1.8867 (19)	C5—H5A	0.92 (3)
O1—N2	1.376 (2)	C7—C8	1.424 (3)
O1—C7	1.431 (2)	C8—C9	1.477 (3)
O2—C7	1.193 (3)	C9—C10	1.480 (3)
O3—C9	1.213 (3)	C10—C11	1.335 (3)
N1—N2	1.303 (2)	C11—C12	1.462 (3)
N1—C8	1.359 (2)	C11—H11A	0.93 (2)
N1—C6	1.450 (2)	C12—C13	1.396 (3)
C1—C6	1.377 (3)	C12—C17	1.405 (3)
C1—C2	1.380 (3)	C13—C14	1.380 (3)
C1—H1A	0.93 (3)	C13—H13A	0.94 (2)
C2—C3	1.374 (4)	C14—C15	1.376 (4)
C2—H2A	0.87 (3)	C14—H14A	0.96 (3)
C3—C4	1.373 (4)	C15—C16	1.368 (4)
C3—H3A	0.93 (3)	C15—H15A	0.93 (3)
C4—C5	1.387 (3)	C16—C17	1.377 (4)
C4—H4A	0.92 (3)	C16—H16A	0.95 (3)
C5—C6	1.373 (3)	C17—H17A	0.97 (3)
N2—O1—C7	111.17 (15)	C7—C8—C9	131.22 (18)
N2—N1—C8	115.34 (16)	O3—C9—C8	118.59 (19)
N2—N1—C6	117.16 (16)	O3—C9—C10	122.82 (19)
C8—N1—C6	127.29 (16)	C8—C9—C10	118.59 (17)
N1—N2—O1	104.55 (15)	C11—C10—C9	122.08 (18)
C6—C1—C2	118.1 (2)	C11—C10—Br1	125.70 (16)
C6—C1—H1A	119.2 (16)	C9—C10—Br1	112.17 (15)
C2—C1—H1A	122.8 (16)	C10—C11—C12	134.49 (19)
C3—C2—C1	120.7 (2)	C10—C11—H11A	112.3 (13)
C3—C2—H2A	122.1 (19)	C12—C11—H11A	113.2 (14)
C1—C2—H2A	117.2 (19)	C13—C12—C17	117.8 (2)
C4—C3—C2	120.0 (2)	C13—C12—C11	116.55 (19)
C4—C3—H3A	121.3 (17)	C17—C12—C11	125.6 (2)
C2—C3—H3A	118.7 (17)	C14—C13—C12	121.4 (2)
C3—C4—C5	120.6 (2)	C14—C13—H13A	122.0 (15)
C3—C4—H4A	120.5 (18)	C12—C13—H13A	116.5 (14)
C5—C4—H4A	118.9 (18)	C15—C14—C13	119.7 (2)
C6—C5—C4	118.0 (2)	C15—C14—H14A	121.0 (17)
C6—C5—H5A	118.9 (15)	C13—C14—H14A	119.4 (17)
C4—C5—H5A	123.2 (15)	C16—C15—C14	119.9 (2)
C5—C6—C1	122.6 (2)	C16—C15—H15A	119.6 (19)
C5—C6—N1	119.33 (18)	C14—C15—H15A	120.4 (19)
C1—C6—N1	118.08 (18)	C15—C16—C17	121.5 (2)
O2—C7—C8	136.9 (2)	C15—C16—H16A	120 (2)
O2—C7—O1	120.12 (19)	C17—C16—H16A	118 (2)
C8—C7—O1	102.93 (16)	C16—C17—C12	119.7 (3)
N1—C8—C7	105.97 (17)	C16—C17—H17A	120.5 (17)
N1—C8—C9	121.14 (17)	C12—C17—H17A	119.8 (17)
C8—N1—N2—O1	1.9 (2)	O2—C7—C8—C9	−14.3 (4)
C6—N1—N2—O1	176.99 (14)	O1—C7—C8—C9	164.64 (19)
C7—O1—N2—N1	−2.04 (18)	N1—C8—C9—O3	34.8 (3)
C6—C1—C2—C3	−0.3 (4)	C7—C8—C9—O3	−128.2 (2)
C1—C2—C3—C4	0.1 (5)	N1—C8—C9—C10	−144.59 (19)
C2—C3—C4—C5	−0.1 (5)	C7—C8—C9—C10	52.3 (3)
C3—C4—C5—C6	0.3 (4)	O3—C9—C10—C11	−169.2 (2)
C4—C5—C6—C1	−0.6 (4)	C8—C9—C10—C11	10.2 (3)
C4—C5—C6—N1	179.9 (2)	O3—C9—C10—Br1	8.3 (3)
C2—C1—C6—C5	0.5 (4)	C8—C9—C10—Br1	−172.26 (15)
C2—C1—C6—N1	−180.0 (2)	C9—C10—C11—C12	179.9 (2)
N2—N1—C6—C5	57.7 (3)	Br1—C10—C11—C12	2.7 (4)
C8—N1—C6—C5	−127.9 (2)	C10—C11—C12—C13	−171.1 (2)
N2—N1—C6—C1	−121.9 (2)	C10—C11—C12—C17	11.2 (4)
C8—N1—C6—C1	52.6 (3)	C17—C12—C13—C14	−1.0 (4)
N2—O1—C7—O2	−179.32 (17)	C11—C12—C13—C14	−178.9 (2)
N2—O1—C7—C8	1.49 (18)	C12—C13—C14—C15	0.5 (4)
N2—N1—C8—C7	−1.0 (2)	C13—C14—C15—C16	0.0 (4)
C6—N1—C8—C7	−175.51 (16)	C14—C15—C16—C17	−0.1 (5)
N2—N1—C8—C9	−167.81 (17)	C15—C16—C17—C12	−0.4 (5)
C6—N1—C8—C9	17.6 (3)	C13—C12—C17—C16	0.9 (4)
O2—C7—C8—N1	−179.3 (2)	C11—C12—C17—C16	178.6 (3)
O1—C7—C8—N1	−0.36 (18)

Cg1 is the centroid of the C12–C17 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O3i	0.87 (3)	2.58 (3)	3.126 (3)	122 (2)
C3—H3A···O3i	0.93 (3)	2.53 (3)	3.140 (4)	124 (2)
C5—H5A···O2ii	0.92 (3)	2.47 (3)	3.388 (3)	171 (2)
C17—H17A···Br1	0.97 (3)	2.66 (3)	3.364 (3)	130 (3)
C14—H14A···Cg1iii	0.96 (3)	2.86 (3)	3.639 (3)	139 (2)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12–C17 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O3i	0.87 (3)	2.58 (3)	3.126 (3)	122 (2)
C3—H3A⋯O3i	0.93 (3)	2.53 (3)	3.140 (4)	124 (2)
C5—H5A⋯O2ii	0.92 (3)	2.47 (3)	3.388 (3)	171 (2)
C17—H17A⋯Br1	0.97 (3)	2.66 (3)	3.364 (3)	130 (3)
C14—H14A⋯Cg1iii	0.96 (3)	2.86 (3)	3.639 (3)	139 (2)

Symmetry codes: (i) ; (ii) ; (iii) .