3-(4-Chloro­phen­yl)-4-phenyl­thio­sydnone

Grossie, D.A.; Turnbull, K.

doi:10.1107/S2414314616015868

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 10| October 2016| x161586

https://doi.org/10.1107/S2414314616015868

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3-(4-Chlorophenyl)-4-phenylthiosydnone

David A. Grossie ^a ^* and Kenneth Turnbull ^a

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

Edited by J. Simpson, University of Otago, New Zealand (Received 21 September 2016; accepted 7 October 2016; online 14 October 2016)

In the structure of C₁₄H₉ClN₂O₂S [systematic name: 3-(4-chlorophenyl)-4-(phenylsulfanyl)-1,2,3λ⁵-oxadiazol-3-ylium-5-olate], the central sydnone ring is inclined at angles of 67.49 (10)° to the phenyl ring of the thiophenyl substituent and 52.61 (10)° to the chlorophenyl ring. The compound crystallizes utilizing a network of weak S and Cl-based hydrogen bonds, together with S⋯π, O⋯π and C—H⋯π interactions, forming a three-dimensional structure. In spite of having three planar rings, no π–π interactions are found.

Keywords: crystal structure; sydnone; hydrogen bonds; X—π interactions X = O; S.

CCDC reference: 1508848

Structure description

The title compound was prepared as part of a project exploring the lithiation chemistry of substituted arylsydnones with the expectation that improved avenues to otherwise difficultly accessible sydnones would result (Grossie, et al., 2007 ; Turnbull & Krein, 1997 ; Turnbull et al., 1998 ). The sydnone and phenyl rings in the title molecule, Fig. 1, are each planar with a maximum r.m.s. deviation of less than 0.01 Å found for all three rings. None of the three rings are coplanar with each other nor are they in close face-to-face proximity. Relative to the sydnone ring, the phenyl ring of the thiophenyl substituent is inclined at an angle of 67.49 (10)° while the sydnone and chlorophenyl rings are rotated by 52.61 (10)° to one another.

Figure 1
The molecular structure of the title compound with ellipsoids drawn at the 50% probability level.

In the crystal, no classical hydrogen bonds are found; however, non-classical hydrogen bonds are present involving sulfur and chlorine as the hydrogen-bond acceptor and carbon as the hydrogen-bond donor. A C—H⋯π hydrogen bond is also found, Table 1. In addition there are S⋯π and O⋯π, contacts, Fig. 2, with distance and angle data detailed in Table 2 and 3. Molecules are also linked into sets of three, on one side by C—H⋯Cl hydrogen bonds and on the other by O⋯π interactions. These trimers are interconnected by a C32—H32⋯S1 hydrogen bond forming a chain of molecules approximately along the bc diagonal, Fig. 3. Overall these contacts combine to generate an extensive three-dimensional network.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C41–C46 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C46—H46⋯Cl1ⁱ	0.93	2.96	3.388 (2)	109
C32—H32⋯S1ⁱⁱ	0.93	2.99	3.797 (2)	146
C33—H33⋯Cg1ⁱⁱⁱ	0.93	2.74	3.498 (2)	140
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[x+1, -y-{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Table 2
Analysis of Y—X⋯Cg(π-ring) interactions (Å, °)

Gamma is the angle between the Cg–H vector and the normal to the ring. Cg2 is the centroid of the O1/N2/N3/C4/C5 ring.

Y—X⋯Cg	X⋯Cg	X-Perp	Gamma	Y—X⋯Cg
C5—O5⋯Cg2ⁱⁱ	3.529 (2)	3.261	22.45	140.29 (14)
Symmetry code: (ii) −x + $[{3\over 2}]$ , y + $[{1\over 2}]$ , z.

Table 3
Analysis of lone pair–π ring [X⋯Cg(π-ring)] interactions (Å, °)

Cg1 and Cg3 are the centroids of the C41–C46 and C31–C36 rings, respectively.

X⋯Cg	X⋯Cg	Y—X⋯Cg	X-Perp	Gamma
S1⋯Cg1	3.487 (2)	95.73	3.447	8.69
O1⋯Cg3	3.349 (3)	118.55	3.188	17.84
Symmetry codes: (iii) −x + $[{3\over 2}]$ , y − $[{1\over 2}]$ , z; (iv) −x + 1, y- 1/2, −z + $[{1\over 2}]$ .

Figure 2
C—H⋯π and X⋯π contacts.

Figure 3
Chains of molecules along the bc diagonal.

Synthesis and crystallization

The title compound was prepared from 3-(4-chlorophenyl)sydnone by treatment with n-BuLi (1.7 equivalents) at −40°C followed by addition of diphenyl disulfide (1.1 equivalents). Column chromatography on silica gel using dichloromethane as eluent and subsequent recrystallization from dichloromethane solution afforded the product as colorless needles in 57% yield (Dossa, 2006 ).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 4.

Table 4
Experimental details

Crystal data
Chemical formula	C₁₄H₉ClN₂O₂S
M_r	304.74
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	173
a, b, c (Å)	12.5782 (11), 9.7406 (9), 22.2168 (19)
V (Å³)	2722.0 (4)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.44
Crystal size (mm)	0.7 × 0.7 × 0.6

Data collection
Diffractometer	Bruker Smart X2S
Absorption correction	Multi-scan (SADABS; Bruker, 2014 )
T_min, T_max	0.904, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	33900, 2973, 2413
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.091, 1.04
No. of reflections	2973
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.47
Computer programs: APEX2 and SAINT (Bruker, 2014), SHELXT2014 (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ), PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2008 )'.

Structural data

CCDC reference: 1508848

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314616015868/sj4059sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616015868/sj4059Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: APEX2 (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009), PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)'.

3-(4-Chlorophenyl)-4-(phenylsulfanyl)-1,2,3λ⁵-oxadiazol-3-ylium-5-olate top

Crystal data top

C₁₄H₉ClN₂O₂S	D_x = 1.487 Mg m⁻³
M_r = 304.74	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 7304 reflections
a = 12.5782 (11) Å	θ = 2.4–23.9°
b = 9.7406 (9) Å	µ = 0.44 mm⁻¹
c = 22.2168 (19) Å	T = 173 K
V = 2722.0 (4) Å³	Block, yellow
Z = 8	0.7 × 0.7 × 0.6 mm
F(000) = 1248

Data collection top

Bruker Smart X2S diffractometer	2413 reflections with I > 2σ(I)
Radiation source: Incoatec Microfocus Source	R_int = 0.048
ω scans	θ_max = 27.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −16→15
T_min = 0.904, T_max = 1.000	k = −11→12
33900 measured reflections	l = −28→28
2973 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.033P)² + 1.677P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2973 reflections	Δρ_max = 0.38 e Å⁻³
181 parameters	Δρ_min = −0.47 e Å⁻³
0 restraints

Special details top

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.

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

Ring 1 7.261 (10) x + 7.749 (6) y + -4.09 (2) z = 4.563 (9)

* 0.007 (2) O(1) * -0.003 (2) N(2) * -0.003 (2) N(3) * 0.007 (2) C(4) * -0.008 (2) C(5)

Ring 2 0.671 (11) x + -6.051 (6) y + 17.371 (11) z = 4.516 (8)

* -0.005 (2) C(31) * -0.002 (2) C(32) * 0.007 (2) C(33) * -0.006 (2) C(34) * 0.000 (2) C(35) * 0.006 (2) C(36)

Ring 3 -6.513 (9) x + 8.333 (4) y + -0.141 (19) z = -3.552 (12)

* -0.008 (2) C(41) * 0.000 (2) C(42) * 0.007 (2) C(43) * -0.006 (2) C(44) * -0.003 (2) C(45) * 0.010 (2) C(46)

Ring Ring Angle

1 2 52.61 (10) 1 3 67.49 (10) 2 3 55.67 (10)

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

	x	y	z	U_iso*/U_eq
S1	0.70839 (4)	0.11292 (5)	0.39942 (2)	0.03326 (13)
Cl1	0.28185 (5)	0.54265 (6)	0.43739 (4)	0.0711 (2)
O1	0.64891 (13)	0.10104 (17)	0.22602 (6)	0.0549 (4)
N3	0.58757 (12)	0.19843 (16)	0.30413 (6)	0.0346 (3)
O5	0.79114 (13)	−0.01484 (17)	0.26453 (6)	0.0563 (4)
N2	0.56899 (15)	0.18549 (19)	0.24655 (8)	0.0509 (5)
C31	0.51284 (15)	0.28083 (19)	0.33771 (8)	0.0349 (4)
C4	0.67396 (15)	0.12955 (18)	0.32453 (8)	0.0325 (4)
C41	0.82162 (15)	0.22185 (18)	0.40756 (8)	0.0324 (4)
C5	0.71701 (17)	0.0605 (2)	0.27391 (8)	0.0422 (5)
C32	0.55037 (16)	0.38634 (19)	0.37319 (9)	0.0390 (4)
H32	0.6229	0.4035	0.3762	0.047*
C46	0.85093 (17)	0.2479 (2)	0.46683 (9)	0.0433 (5)
H46	0.8082	0.2174	0.4983	0.052*
C36	0.40563 (15)	0.2517 (2)	0.33229 (9)	0.0427 (5)
H36	0.3824	0.1791	0.3085	0.051*
C42	0.88276 (15)	0.2698 (2)	0.36062 (9)	0.0408 (4)
H42	0.8627	0.2534	0.3210	0.049*
C34	0.37116 (16)	0.4392 (2)	0.39826 (10)	0.0447 (5)
C33	0.47785 (17)	0.4662 (2)	0.40430 (9)	0.0447 (5)
H33	0.5010	0.5372	0.4290	0.054*
C35	0.33365 (16)	0.3330 (2)	0.36306 (10)	0.0478 (5)
H35	0.2610	0.3163	0.3601	0.057*
C43	0.97527 (17)	0.3432 (2)	0.37342 (11)	0.0537 (6)
H43	1.0170	0.3769	0.3422	0.064*
C44	1.00502 (18)	0.3659 (2)	0.43267 (13)	0.0599 (7)
H44	1.0674	0.4134	0.4410	0.072*
C45	0.9434 (2)	0.3189 (2)	0.47894 (11)	0.0568 (6)
H45	0.9638	0.3348	0.5186	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0378 (3)	0.0360 (2)	0.0261 (2)	−0.00063 (19)	−0.00220 (18)	0.00344 (18)
Cl1	0.0543 (4)	0.0476 (3)	0.1115 (5)	0.0168 (3)	0.0348 (3)	0.0146 (3)
O1	0.0634 (10)	0.0715 (11)	0.0299 (7)	0.0099 (8)	−0.0076 (6)	−0.0115 (7)
N3	0.0378 (9)	0.0376 (8)	0.0283 (7)	−0.0029 (7)	−0.0045 (6)	0.0009 (6)
O5	0.0579 (10)	0.0635 (10)	0.0476 (9)	0.0153 (8)	0.0020 (7)	−0.0154 (8)
N2	0.0561 (11)	0.0646 (12)	0.0319 (8)	0.0078 (9)	−0.0108 (8)	−0.0033 (8)
C31	0.0343 (10)	0.0358 (10)	0.0345 (9)	0.0007 (8)	−0.0003 (7)	0.0078 (8)
C4	0.0345 (10)	0.0343 (9)	0.0288 (8)	0.0002 (8)	−0.0026 (7)	−0.0001 (7)
C41	0.0346 (9)	0.0278 (9)	0.0349 (9)	0.0067 (7)	−0.0034 (7)	−0.0040 (7)
C5	0.0474 (12)	0.0477 (11)	0.0315 (9)	−0.0012 (10)	−0.0035 (8)	−0.0051 (8)
C32	0.0335 (10)	0.0353 (10)	0.0482 (11)	−0.0051 (8)	0.0052 (8)	0.0025 (8)
C46	0.0562 (13)	0.0364 (10)	0.0374 (10)	0.0060 (10)	−0.0103 (9)	−0.0066 (8)
C36	0.0357 (11)	0.0458 (11)	0.0464 (11)	−0.0044 (9)	−0.0083 (9)	0.0088 (9)
C42	0.0412 (11)	0.0377 (10)	0.0435 (10)	0.0002 (9)	0.0055 (9)	−0.0103 (9)
C34	0.0379 (11)	0.0353 (10)	0.0610 (13)	0.0077 (9)	0.0142 (9)	0.0187 (10)
C33	0.0447 (12)	0.0323 (10)	0.0570 (12)	−0.0033 (9)	0.0127 (10)	0.0022 (9)
C35	0.0287 (10)	0.0526 (13)	0.0623 (13)	−0.0004 (9)	−0.0012 (9)	0.0196 (11)
C43	0.0427 (12)	0.0421 (12)	0.0763 (16)	−0.0027 (10)	0.0171 (11)	−0.0167 (11)
C44	0.0400 (12)	0.0426 (12)	0.0972 (19)	0.0029 (10)	−0.0145 (13)	−0.0307 (13)
C45	0.0610 (15)	0.0480 (13)	0.0615 (14)	0.0078 (11)	−0.0218 (12)	−0.0191 (11)

Geometric parameters (Å, º) top

S1—C4	1.7268 (17)	C46—H46	0.9300
S1—C41	1.7852 (19)	C46—C45	1.380 (3)
Cl1—C34	1.742 (2)	C36—H36	0.9300
O1—N2	1.377 (2)	C36—C35	1.383 (3)
O1—C5	1.422 (2)	C42—H42	0.9300
N3—N2	1.307 (2)	C42—C43	1.395 (3)
N3—C31	1.444 (2)	C34—C33	1.374 (3)
N3—C4	1.355 (2)	C34—C35	1.380 (3)
O5—C5	1.205 (2)	C33—H33	0.9300
C31—C32	1.379 (3)	C35—H35	0.9300
C31—C36	1.383 (3)	C43—H43	0.9300
C4—C5	1.418 (3)	C43—C44	1.386 (3)
C41—C46	1.391 (2)	C44—H44	0.9300
C41—C42	1.377 (3)	C44—C45	1.366 (4)
C32—H32	0.9300	C45—H45	0.9300
C32—C33	1.384 (3)

C4—S1—C41	104.00 (9)	C31—C36—H36	120.7
N2—O1—C5	110.98 (14)	C31—C36—C35	118.5 (2)
N2—N3—C31	116.30 (15)	C35—C36—H36	120.7
N2—N3—C4	115.04 (16)	C41—C42—H42	120.5
C4—N3—C31	128.65 (14)	C41—C42—C43	119.01 (19)
N3—N2—O1	104.56 (15)	C43—C42—H42	120.5
C32—C31—N3	119.14 (16)	C33—C34—Cl1	118.05 (18)
C32—C31—C36	122.44 (19)	C33—C34—C35	122.20 (19)
C36—C31—N3	118.42 (17)	C35—C34—Cl1	119.75 (16)
N3—C4—S1	124.74 (13)	C32—C33—H33	120.4
N3—C4—C5	106.01 (15)	C34—C33—C32	119.2 (2)
C5—C4—S1	128.61 (15)	C34—C33—H33	120.4
C46—C41—S1	114.58 (15)	C36—C35—H35	120.5
C42—C41—S1	124.76 (14)	C34—C35—C36	119.03 (19)
C42—C41—C46	120.47 (19)	C34—C35—H35	120.5
O5—C5—O1	120.41 (17)	C42—C43—H43	120.0
O5—C5—C4	136.19 (19)	C44—C43—C42	120.0 (2)
C4—C5—O1	103.40 (17)	C44—C43—H43	120.0
C31—C32—H32	120.7	C43—C44—H44	119.7
C31—C32—C33	118.61 (18)	C45—C44—C43	120.5 (2)
C33—C32—H32	120.7	C45—C44—H44	119.7
C41—C46—H46	120.0	C46—C45—H45	120.0
C45—C46—C41	120.0 (2)	C44—C45—C46	120.0 (2)
C45—C46—H46	120.0	C44—C45—H45	120.0

S1—C4—C5—O1	172.40 (14)	C31—C36—C35—C34	−0.5 (3)
S1—C4—C5—O5	−8.6 (4)	C4—S1—C41—C46	167.36 (14)
S1—C41—C46—C45	173.35 (16)	C4—S1—C41—C42	−17.73 (18)
S1—C41—C42—C43	−173.76 (15)	C4—N3—N2—O1	0.0 (2)
Cl1—C34—C33—C32	−179.33 (15)	C4—N3—C31—C32	54.0 (3)
Cl1—C34—C35—C36	−179.97 (15)	C4—N3—C31—C36	−126.9 (2)
N3—C31—C32—C33	178.85 (17)	C41—S1—C4—N3	−107.63 (16)
N3—C31—C36—C35	−178.18 (16)	C41—S1—C4—C5	82.94 (19)
N3—C4—C5—O1	1.4 (2)	C41—C46—C45—C44	1.3 (3)
N3—C4—C5—O5	−179.5 (2)	C41—C42—C43—C44	0.6 (3)
N2—O1—C5—O5	179.30 (19)	C5—O1—N2—N3	0.9 (2)
N2—O1—C5—C4	−1.5 (2)	C32—C31—C36—C35	0.9 (3)
N2—N3—C31—C32	−127.57 (19)	C46—C41—C42—C43	0.9 (3)
N2—N3—C31—C36	51.6 (2)	C36—C31—C32—C33	−0.2 (3)
N2—N3—C4—S1	−172.41 (15)	C42—C41—C46—C45	−1.8 (3)
N2—N3—C4—C5	−1.0 (2)	C42—C43—C44—C45	−1.1 (3)
C31—N3—N2—O1	−178.59 (15)	C33—C34—C35—C36	−0.7 (3)
C31—N3—C4—S1	6.0 (3)	C35—C34—C33—C32	1.4 (3)
C31—N3—C4—C5	177.46 (17)	C43—C44—C45—C46	0.2 (3)
C31—C32—C33—C34	−0.9 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C41–C46 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C46—H46···Cl1ⁱ	0.93	2.96	3.388 (2)	109
C32—H32···S1ⁱⁱ	0.93	2.99	3.797 (2)	146
C33—H33···Cg1ⁱⁱⁱ	0.93	2.74	3.498 (2)	140

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, y+1/2, z; (iii) x+1, −y−3/2, z−1/2.

Analysis of Y—X···Cg(π-ring) interactions (Å, °) top

Gamma is the angle between the Cg–H vector and the normal to the ring. Cg2 is the centroid of the O1/N2/N3/C4/C5 ring.

Y—X···Cg	X···Cg	X-Perp	Gamma	Y—X···Cg
C5—O5···Cg2ⁱⁱ	3.529 (2)	3.261	22.45	140.29 (14)

Symmetry code: (ii) -x + 3/2, y + 1/2, z.

Analysis of lone pair–π ring [X···Cg(π-ring)] interactions (Å, °) top

Cg1 and Cg3 are the centroids of the C41–C46 and C31–C36 rings, respectively.

X···Cg	X···Cg	Y—X···Cg	X-Perp	Gamma
S1···Cg1	3.487 (2)	95.73	3.447	8.69
O1···Cg3	3.349 (3)	118.55	3.188	17.84

Symmetry codes: (iii) -x + 3/2, y - 1/2, z; (iv) -x + 1, y- 1/2, -z + 1/2.

References

Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Dossa, A. (2006). MSc thesis, Wright State University, USA. Google Scholar
Grossie, D. A., Sun, L. & Turnbull, K. (2007). Acta Cryst. E63, o2042–o2043. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Turnbull, K. & Krein, D. M. (1997). Tetrahedron Lett. 38, 1165–1168. CrossRef CAS Web of Science Google Scholar
Turnbull, K., Sun, C. & Krein, D. M. (1998). Tetrahedron Lett. 39, 1509–1512. Web of Science CrossRef CAS Google Scholar

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ISSN: 2414-3146

Volume 1| Part 10| October 2016| x161586

https://doi.org/10.1107/S2414314616015868

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

3-(4-Chloro­phen­yl)-4-phenyl­thio­sydnone

Structure description

Synthesis and crystallization

Refinement

Structural data

References

organic compounds

3-(4-Chlorophenyl)-4-phenylthiosydnone