4,4',5,5'-Tetra­phenyl-2,2'-dithiodi-1,3-oxazole

The asymmetric unit of the title compound, C₃₀H₂₀N₂O₂S₂, contains one-half of the mol­ecule; a twofold rotation axis passes through the mid-point of the S-S bond. In the mol­ecule, the S-S bond length is 2.049 (2) Å.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.052
• wR factor = 0.108
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         39 Perc.

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.127
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.13
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) .....         12 Ang.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     -   C14     ..       5.84 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     -   C15     ..       6.88 su
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

In the title molecule (Fig. 1) the S—S bond length is 2.049 (2) Å, which is consistent with the literature data (Schroth et al., 1998).

Related literature

For normal values of S—S bond lengths in organic compounds, see: Schroth et al. (1998).

S2. Experimental

To an ethanol (10 ml) solution of 4,5-diphenyl-2-mercaptooxazole (1 mmol) was added an ethanol (5 ml) solution of iodine (2 mmol). The mixture was stirring for 3 h at room temperature, an colorless solution was obtained, which was filtered. The filtrate was left undisturbed at room temperature for two weeks. Crystals of the title compound suitable for X-ray analysis were grown from an ethanol solution (yield 60%).

S3. Refinement

All H atoms were placed in geometrically idealized positions (C—H 0.93 Å) and treated as riding on their parent atoms, with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures

Fig. 1. The molecular structure of the title compound showing the atomic numbering and 30% probability displacement ellipsoids [symmetry code: (A) -x + 2, y, -z + 1/2].

4,4',5,5'-Tetraphenyl-2,2'-dithiodi-1,3-oxazole

Crystal data

C30H20N2O2S2	F(000) = 1048
Mr = 504.60	Dx = 1.327 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2a b	Cell parameters from 1176 reflections
a = 30.60540 (12) Å	θ = 2.7–19.4°
b = 10.1073 (4) Å	µ = 0.24 mm^−1
c = 8.1631 (3) Å	T = 298 K
V = 2525.16 (14) Å^3	Block, colourless
Z = 4	0.20 × 0.16 × 0.08 mm

Data collection

Siemens SMART CCD area-detector diffractometer	2167 independent reflections
Radiation source: fine-focus sealed tube	847 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.127
ϕ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −36→35
Tmin = 0.953, Tmax = 0.981	k = −10→12
11778 measured reflections	l = −9→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.026P)^2] where P = (Fo^2 + 2Fc^2)/3
2167 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.90107 (11)	0.7419 (3)	0.2113 (4)	0.0480 (9)
O1	0.94457 (9)	0.5774 (3)	0.2838 (3)	0.0627 (9)
S1	0.97796 (4)	0.81655 (10)	0.34446 (15)	0.0691 (4)
C1	0.90583 (14)	0.3774 (4)	0.2110 (5)	0.0459 (11)
C2	0.87761 (12)	0.3110 (4)	0.1066 (5)	0.0553 (12)
H2	0.8582	0.3585	0.0414	0.066*
C3	0.87819 (13)	0.1759 (4)	0.0993 (5)	0.0591 (12)
H3	0.8593	0.1327	0.0280	0.071*
C4	0.90618 (16)	0.1022 (4)	0.1953 (6)	0.0667 (14)
H4	0.9056	0.0102	0.1915	0.080*
C5	0.93462 (16)	0.1664 (4)	0.2956 (6)	0.0711 (14)
H5	0.9540	0.1176	0.3593	0.085*
C6	0.93523 (14)	0.3028 (4)	0.3045 (6)	0.0661 (13)
H6	0.9552	0.3452	0.3727	0.079*
C7	0.83519 (13)	0.6307 (4)	0.1133 (5)	0.0445 (11)
C8	0.80258 (14)	0.5447 (4)	0.1608 (5)	0.0591 (12)
H8	0.8090	0.4778	0.2352	0.071*
C9	0.76072 (15)	0.5555 (5)	0.1006 (6)	0.0696 (14)
H9	0.7391	0.4969	0.1340	0.084*
C10	0.75143 (19)	0.6547 (6)	−0.0098 (7)	0.0871 (19)
H10	0.7234	0.6617	−0.0530	0.104*
C11	0.7829 (2)	0.7432 (6)	−0.0567 (6)	0.0845 (17)
H11	0.7760	0.8108	−0.1295	0.101*
C12	0.82454 (15)	0.7323 (4)	0.0034 (5)	0.0555 (12)
H12	0.8458	0.7925	−0.0288	0.067*
C13	0.87958 (14)	0.6239 (4)	0.1786 (4)	0.0447 (11)
C14	0.90666 (13)	0.5217 (4)	0.2202 (5)	0.0482 (11)
C15	0.93823 (15)	0.7093 (4)	0.2735 (5)	0.0504 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.046 (2)	0.0399 (19)	0.058 (2)	−0.0002 (18)	−0.0060 (19)	0.0021 (18)
O1	0.065 (2)	0.0476 (18)	0.075 (2)	0.0027 (16)	−0.0032 (17)	−0.0059 (16)
S1	0.0714 (8)	0.0506 (7)	0.0854 (10)	0.0046 (6)	−0.0135 (7)	−0.0172 (7)
C1	0.063 (3)	0.036 (2)	0.039 (3)	−0.003 (2)	0.006 (2)	0.003 (2)
C2	0.063 (3)	0.039 (3)	0.064 (3)	0.009 (2)	−0.007 (3)	0.005 (3)
C3	0.070 (3)	0.042 (3)	0.065 (3)	0.008 (2)	−0.002 (3)	−0.009 (3)
C4	0.079 (4)	0.025 (3)	0.097 (4)	0.008 (2)	−0.001 (3)	0.001 (3)
C5	0.086 (4)	0.044 (3)	0.083 (4)	0.015 (3)	−0.010 (3)	0.008 (3)
C6	0.076 (3)	0.042 (3)	0.080 (4)	0.009 (2)	−0.012 (3)	−0.002 (3)
C7	0.051 (3)	0.039 (2)	0.043 (3)	0.007 (2)	0.001 (2)	0.001 (2)
C8	0.057 (3)	0.051 (3)	0.069 (3)	0.001 (2)	0.006 (3)	−0.005 (3)
C9	0.058 (4)	0.079 (4)	0.072 (4)	−0.002 (3)	0.008 (3)	−0.026 (3)
C10	0.075 (5)	0.108 (5)	0.077 (5)	0.037 (4)	−0.010 (3)	−0.030 (4)
C11	0.084 (5)	0.100 (4)	0.070 (4)	0.032 (4)	−0.002 (3)	0.004 (3)
C12	0.067 (4)	0.044 (3)	0.056 (3)	0.012 (2)	0.008 (3)	0.003 (2)
C13	0.066 (3)	0.039 (2)	0.029 (3)	0.005 (2)	−0.004 (2)	0.001 (2)
C14	0.052 (3)	0.040 (3)	0.053 (3)	−0.011 (2)	−0.004 (2)	0.001 (2)
C15	0.065 (3)	0.034 (3)	0.053 (3)	−0.003 (2)	0.007 (2)	−0.002 (2)

Geometric parameters (Å, º)

N1—C15	1.288 (4)	C5—H5	0.9300
N1—C13	1.388 (4)	C6—H6	0.9300
O1—C15	1.350 (4)	C7—C8	1.379 (5)
O1—C14	1.390 (4)	C7—C12	1.402 (5)
S1—C15	1.729 (4)	C7—C13	1.461 (5)
S1—S1^i	2.049 (2)	C8—C9	1.376 (5)
C1—C2	1.386 (5)	C8—H8	0.9300
C1—C6	1.400 (5)	C9—C10	1.377 (6)
C1—C14	1.461 (5)	C9—H9	0.9300
C2—C3	1.367 (4)	C10—C11	1.369 (6)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.380 (5)	C11—C12	1.369 (5)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.360 (5)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.367 (5)
C5—C6	1.381 (5)
C15—N1—C13	106.0 (3)	C9—C8—C7	121.6 (4)
C15—O1—C14	104.8 (3)	C9—C8—H8	119.2
C15—S1—S1^i	102.18 (14)	C7—C8—H8	119.2
C2—C1—C6	118.4 (4)	C8—C9—C10	118.9 (5)
C2—C1—C14	121.7 (4)	C8—C9—H9	120.5
C6—C1—C14	119.9 (4)	C10—C9—H9	120.5
C3—C2—C1	120.2 (4)	C11—C10—C9	120.8 (5)
C3—C2—H2	119.9	C11—C10—H10	119.6
C1—C2—H2	119.9	C9—C10—H10	119.6
C2—C3—C4	121.5 (4)	C10—C11—C12	120.2 (5)
C2—C3—H3	119.2	C10—C11—H11	119.9
C4—C3—H3	119.2	C12—C11—H11	119.9
C5—C4—C3	118.8 (4)	C11—C12—C7	120.3 (4)
C5—C4—H4	120.6	C11—C12—H12	119.9
C3—C4—H4	120.6	C7—C12—H12	119.9
C4—C5—C6	121.2 (4)	C14—C13—N1	108.3 (3)
C4—C5—H5	119.4	C14—C13—C7	133.6 (4)
C6—C5—H5	119.4	N1—C13—C7	118.1 (3)
C5—C6—C1	120.0 (4)	C13—C14—O1	107.1 (3)
C5—C6—H6	120.0	C13—C14—C1	137.0 (4)
C1—C6—H6	120.0	O1—C14—C1	115.9 (4)
C8—C7—C12	118.2 (4)	N1—C15—O1	113.8 (3)
C8—C7—C13	122.8 (4)	N1—C15—S1	126.4 (3)
C12—C7—C13	118.9 (4)	O1—C15—S1	119.8 (3)
C6—C1—C2—C3	1.4 (6)	C12—C7—C13—C14	−145.1 (4)
C14—C1—C2—C3	179.0 (4)	C8—C7—C13—N1	−140.9 (4)
C1—C2—C3—C4	0.6 (6)	C12—C7—C13—N1	36.1 (5)
C2—C3—C4—C5	−1.9 (6)	N1—C13—C14—O1	1.8 (4)
C3—C4—C5—C6	1.2 (7)	C7—C13—C14—O1	−177.0 (4)
C4—C5—C6—C1	0.9 (7)	N1—C13—C14—C1	−176.5 (4)
C2—C1—C6—C5	−2.2 (6)	C7—C13—C14—C1	4.7 (8)
C14—C1—C6—C5	−179.8 (4)	C15—O1—C14—C13	−1.1 (4)
C12—C7—C8—C9	1.2 (6)	C15—O1—C14—C1	177.6 (3)
C13—C7—C8—C9	178.2 (4)	C2—C1—C14—C13	18.9 (7)
C7—C8—C9—C10	0.1 (6)	C6—C1—C14—C13	−163.6 (5)
C8—C9—C10—C11	−1.4 (7)	C2—C1—C14—O1	−159.3 (3)
C9—C10—C11—C12	1.4 (7)	C6—C1—C14—O1	18.2 (5)
C10—C11—C12—C7	0.0 (7)	C13—N1—C15—O1	1.1 (4)
C8—C7—C12—C11	−1.2 (6)	C13—N1—C15—S1	−177.6 (3)
C13—C7—C12—C11	−178.4 (4)	C14—O1—C15—N1	0.0 (4)
C15—N1—C13—C14	−1.8 (4)	C14—O1—C15—S1	178.8 (3)
C15—N1—C13—C7	177.2 (3)	S1^i—S1—C15—N1	−101.7 (4)
C8—C7—C13—C14	37.9 (6)	S1^i—S1—C15—O1	79.6 (3)

Symmetry code: (i) −x+2, y, −z+1/2.