3-{4-[(4-Meth-oxy-benzyl-idene)amino]-3-phenyl-5-sulfanyl-idene-4,5-dihydro-1H-1,2,4-triazol-1-yl}-1,3-diphenyl-propan-1-one.

In the title mol-ecule, C(31)H(26)N(4)O(2)S, the phenyl ring attached to the 1,2,4-triazole ring forms dihedral angles of 65.4 (2), 63.4 (2) and 62.2 (2)° with the other three rings. The 1,2,4-triazole ring makes dihedral angles of 78.0 (2), 87.9 (2), 24.9 (2) and 62.8 (2)° with three phenyl rings and the methoxyphenyl ring.

Related literature

For the crystal structures of related 1,2,4-triazole-5(4H)-thione derivatives, see: Al-Tamimi et al. (2010 ▶); Fun et al. (2009 ▶); Gao et al. (2011 ▶); Tan et al. (2010 ▶); Wang et al. (2011 ▶); Zhao et al. (2010 ▶).

Experimental

Crystal data

C31H26N4O2S

M = 518.62

Monoclinic,

a = 6.0131 (12) Å

b = 13.940 (2) Å

c = 31.490 (4) Å

β = 92.007 (6)°

V = 2638.1 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 113 K

0.20 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.969, T max = 0.984

16481 measured reflections

4616 independent reflections

3734 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.157

S = 1.16

4616 reflections

344 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681103488X/bh2374sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103488X/bh2374Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681103488X/bh2374Isup3.cml

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

C31H26N4O2S	F(000) = 1088
Mr = 518.62	Dx = 1.306 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6676 reflections
a = 6.0131 (12) Å	θ = 1.5–28.0°
b = 13.940 (2) Å	µ = 0.16 mm−1
c = 31.490 (4) Å	T = 113 K
β = 92.007 (6)°	Prism, colourless
V = 2638.1 (8) Å3	0.20 × 0.12 × 0.10 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	4616 independent reflections
Radiation source: rotating anode	3734 reflections with I > 2σ(I)
multilayer	Rint = 0.053
Detector resolution: 14.63 pixels mm-1	θmax = 25.0°, θmin = 1.3°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −16→15
Tmin = 0.969, Tmax = 0.984	l = −37→37
16481 measured reflections

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 1.16	w = 1/[σ2(Fo2) + (0.0562P)2 + 1.9562P] where P = (Fo2 + 2Fc2)/3
4616 reflections	(Δ/σ)max = 0.001
344 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.26 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
S1	0.23615 (15)	0.69419 (6)	0.33669 (3)	0.0366 (3)
O1	0.3196 (5)	0.7950 (2)	0.48255 (9)	0.0547 (8)
O2	0.1052 (4)	0.15537 (16)	0.24902 (7)	0.0337 (6)
N1	0.5402 (4)	0.73453 (18)	0.40025 (8)	0.0282 (6)
N2	0.7135 (4)	0.69513 (18)	0.42388 (8)	0.0271 (6)
N3	0.5571 (4)	0.58826 (17)	0.38083 (8)	0.0245 (6)
N4	0.5420 (4)	0.50339 (17)	0.35608 (8)	0.0253 (6)
C1	0.5395 (7)	0.8105 (3)	0.56280 (13)	0.0468 (10)
H1	0.3998	0.7786	0.5615	0.056*
C2	0.6540 (8)	0.8187 (3)	0.60105 (12)	0.0523 (11)
H2	0.5935	0.7920	0.6259	0.063*
C3	0.8573 (8)	0.8656 (3)	0.60374 (13)	0.0512 (11)
H3	0.9359	0.8710	0.6303	0.061*
C4	0.9454 (7)	0.9043 (3)	0.56763 (12)	0.0482 (10)
H4	1.0840	0.9371	0.5694	0.058*
C5	0.8309 (7)	0.8954 (3)	0.52858 (12)	0.0433 (9)
H5	0.8935	0.9215	0.5038	0.052*
C6	0.6266 (6)	0.8490 (2)	0.52528 (11)	0.0380 (9)
C7	0.4977 (6)	0.8366 (2)	0.48405 (12)	0.0375 (9)
C8	0.5941 (6)	0.8789 (2)	0.44398 (11)	0.0365 (8)
H8A	0.7566	0.8671	0.4447	0.044*
H8B	0.5713	0.9492	0.4442	0.044*
C9	0.4928 (6)	0.8383 (2)	0.40247 (11)	0.0324 (8)
H9	0.3278	0.8475	0.4024	0.039*
C10	0.5829 (6)	0.8909 (2)	0.36457 (11)	0.0330 (8)
C11	0.7910 (6)	0.8697 (3)	0.34881 (11)	0.0387 (9)
H11	0.8776	0.8190	0.3610	0.046*
C12	0.8718 (7)	0.9226 (3)	0.31521 (12)	0.0473 (10)
H12	1.0120	0.9067	0.3041	0.057*
C13	0.7509 (8)	0.9976 (3)	0.29786 (12)	0.0510 (11)
H13	0.8080	1.0343	0.2753	0.061*
C14	0.5448 (9)	1.0187 (3)	0.31375 (14)	0.0624 (13)
H14	0.4607	1.0707	0.3022	0.075*
C15	0.4606 (7)	0.9650 (3)	0.34621 (13)	0.0466 (10)
H15	0.3167	0.9790	0.3561	0.056*
C16	0.4396 (5)	0.6727 (2)	0.37249 (10)	0.0284 (7)
C17	0.7243 (5)	0.6060 (2)	0.41084 (9)	0.0244 (7)
C18	0.8904 (5)	0.5381 (2)	0.42774 (9)	0.0225 (7)
C19	0.8585 (5)	0.4386 (2)	0.42829 (9)	0.0272 (7)
H19	0.7240	0.4117	0.4169	0.033*
C20	1.0228 (6)	0.3795 (2)	0.44547 (10)	0.0306 (8)
H20	1.0005	0.3121	0.4458	0.037*
C21	1.2204 (6)	0.4177 (2)	0.46231 (10)	0.0312 (7)
H21	1.3333	0.3765	0.4737	0.037*
C22	1.2516 (6)	0.5166 (2)	0.46237 (10)	0.0298 (7)
H22	1.3856	0.5430	0.4742	0.036*
C23	1.0891 (5)	0.5767 (2)	0.44532 (9)	0.0261 (7)
H23	1.1116	0.6441	0.4455	0.031*
C24	0.3397 (5)	0.4742 (2)	0.34988 (9)	0.0259 (7)
H24	0.2228	0.5062	0.3637	0.031*
C25	0.2871 (5)	0.3929 (2)	0.32204 (9)	0.0250 (7)
C26	0.0753 (5)	0.3513 (2)	0.32370 (10)	0.0284 (7)
H26	−0.0311	0.3776	0.3420	0.034*
C27	0.0199 (5)	0.2725 (2)	0.29886 (10)	0.0290 (7)
H27	−0.1234	0.2443	0.3003	0.035*
C28	0.1763 (5)	0.2344 (2)	0.27151 (9)	0.0261 (7)
C29	0.3856 (5)	0.2765 (2)	0.26850 (9)	0.0281 (7)
H29	0.4902	0.2516	0.2495	0.034*
C30	0.4381 (5)	0.3550 (2)	0.29371 (9)	0.0256 (7)
H30	0.5804	0.3839	0.2917	0.031*
C31	0.2434 (6)	0.1194 (3)	0.21661 (10)	0.0376 (8)
H31A	0.2660	0.1697	0.1954	0.056*
H31B	0.1713	0.0639	0.2029	0.056*
H31C	0.3875	0.1000	0.2293	0.056*

	U11	U22	U33	U12	U13	U23
S1	0.0310 (5)	0.0299 (5)	0.0482 (5)	0.0041 (4)	−0.0067 (4)	−0.0010 (4)
O1	0.0489 (17)	0.0576 (18)	0.0587 (17)	−0.0203 (15)	0.0179 (14)	−0.0148 (14)
O2	0.0352 (13)	0.0321 (12)	0.0341 (12)	−0.0010 (10)	0.0021 (11)	−0.0119 (10)
N1	0.0257 (15)	0.0209 (13)	0.0379 (15)	0.0004 (11)	0.0020 (12)	−0.0048 (11)
N2	0.0248 (14)	0.0239 (14)	0.0325 (14)	−0.0004 (11)	0.0007 (12)	−0.0030 (11)
N3	0.0248 (14)	0.0188 (13)	0.0299 (13)	0.0006 (11)	−0.0014 (11)	−0.0048 (10)
N4	0.0298 (15)	0.0211 (13)	0.0250 (13)	0.0005 (11)	−0.0005 (11)	−0.0041 (10)
C1	0.055 (3)	0.031 (2)	0.056 (2)	−0.0015 (18)	0.020 (2)	−0.0044 (17)
C2	0.076 (3)	0.042 (2)	0.040 (2)	0.006 (2)	0.018 (2)	−0.0017 (17)
C3	0.068 (3)	0.036 (2)	0.049 (2)	0.010 (2)	0.003 (2)	−0.0068 (18)
C4	0.055 (3)	0.036 (2)	0.054 (2)	−0.0043 (19)	0.005 (2)	−0.0063 (18)
C5	0.051 (2)	0.035 (2)	0.045 (2)	−0.0052 (18)	0.0121 (18)	−0.0039 (16)
C6	0.045 (2)	0.0234 (17)	0.046 (2)	0.0024 (16)	0.0117 (17)	−0.0082 (15)
C7	0.037 (2)	0.0250 (17)	0.051 (2)	−0.0038 (16)	0.0169 (18)	−0.0121 (15)
C8	0.040 (2)	0.0231 (17)	0.047 (2)	−0.0015 (15)	0.0122 (17)	−0.0096 (15)
C9	0.0267 (18)	0.0220 (16)	0.049 (2)	0.0031 (14)	0.0053 (15)	−0.0078 (15)
C10	0.033 (2)	0.0226 (17)	0.0435 (19)	0.0022 (14)	−0.0023 (16)	−0.0047 (14)
C11	0.034 (2)	0.0339 (19)	0.049 (2)	0.0033 (16)	0.0017 (17)	0.0010 (16)
C12	0.046 (2)	0.050 (2)	0.046 (2)	−0.0097 (19)	0.0047 (19)	−0.0053 (18)
C13	0.078 (3)	0.034 (2)	0.041 (2)	−0.013 (2)	0.004 (2)	0.0018 (17)
C14	0.093 (4)	0.039 (2)	0.055 (3)	0.020 (2)	−0.009 (3)	0.006 (2)
C15	0.051 (2)	0.036 (2)	0.053 (2)	0.0170 (18)	0.0025 (19)	0.0011 (18)
C16	0.0260 (18)	0.0243 (17)	0.0353 (17)	−0.0018 (13)	0.0061 (14)	−0.0017 (13)
C17	0.0236 (17)	0.0225 (16)	0.0273 (15)	−0.0033 (13)	0.0035 (13)	−0.0025 (13)
C18	0.0235 (17)	0.0258 (16)	0.0185 (14)	0.0023 (13)	0.0053 (12)	−0.0026 (12)
C19	0.0283 (18)	0.0259 (17)	0.0273 (16)	−0.0038 (14)	0.0009 (14)	−0.0061 (13)
C20	0.039 (2)	0.0224 (16)	0.0308 (17)	0.0015 (14)	−0.0001 (15)	−0.0023 (13)
C21	0.0325 (19)	0.0339 (18)	0.0269 (16)	0.0067 (15)	−0.0014 (14)	−0.0015 (14)
C22	0.0259 (17)	0.0385 (19)	0.0250 (16)	−0.0036 (15)	−0.0011 (14)	0.0014 (14)
C23	0.0311 (18)	0.0244 (16)	0.0230 (15)	−0.0018 (14)	0.0053 (13)	−0.0032 (13)
C24	0.0258 (18)	0.0262 (16)	0.0257 (15)	0.0004 (14)	0.0024 (13)	0.0006 (13)
C25	0.0260 (18)	0.0240 (16)	0.0252 (15)	0.0018 (13)	0.0011 (13)	0.0003 (13)
C26	0.0279 (18)	0.0312 (18)	0.0263 (16)	−0.0005 (14)	0.0031 (14)	−0.0023 (13)
C27	0.0251 (18)	0.0285 (17)	0.0335 (17)	−0.0034 (14)	0.0025 (14)	−0.0036 (14)
C28	0.0311 (19)	0.0233 (16)	0.0238 (15)	0.0003 (14)	−0.0026 (14)	−0.0038 (12)
C29	0.0296 (18)	0.0298 (17)	0.0252 (16)	0.0041 (14)	0.0033 (14)	−0.0006 (13)
C30	0.0230 (17)	0.0270 (17)	0.0272 (15)	0.0002 (13)	0.0050 (13)	0.0010 (13)
C31	0.042 (2)	0.038 (2)	0.0325 (17)	0.0055 (16)	−0.0014 (16)	−0.0146 (15)

S1—C16	1.662 (3)	C12—C13	1.376 (6)
O1—C7	1.218 (4)	C12—H12	0.9500
O2—C28	1.370 (4)	C13—C14	1.384 (6)
O2—C31	1.429 (4)	C13—H13	0.9500
N1—C16	1.355 (4)	C14—C15	1.378 (6)
N1—N2	1.374 (4)	C14—H14	0.9500
N1—C9	1.477 (4)	C15—H15	0.9500
N2—C17	1.310 (4)	C17—C18	1.463 (4)
N3—C17	1.378 (4)	C18—C19	1.401 (4)
N3—C16	1.393 (4)	C18—C23	1.406 (4)
N3—N4	1.418 (3)	C19—C20	1.382 (4)
N4—C24	1.291 (4)	C19—H19	0.9500
C1—C2	1.371 (6)	C20—C21	1.390 (5)
C1—C6	1.415 (5)	C20—H20	0.9500
C1—H1	0.9500	C21—C22	1.392 (5)
C2—C3	1.386 (6)	C21—H21	0.9500
C2—H2	0.9500	C22—C23	1.381 (4)
C3—C4	1.381 (5)	C22—H22	0.9500
C3—H3	0.9500	C23—H23	0.9500
C4—C5	1.394 (5)	C24—C25	1.461 (4)
C4—H4	0.9500	C24—H24	0.9500
C5—C6	1.389 (5)	C25—C30	1.399 (4)
C5—H5	0.9500	C25—C26	1.402 (4)
C6—C7	1.498 (5)	C26—C27	1.383 (4)
C7—C8	1.526 (5)	C26—H26	0.9500
C8—C9	1.531 (5)	C27—C28	1.402 (4)
C8—H8A	0.9900	C27—H27	0.9500
C8—H8B	0.9900	C28—C29	1.395 (4)
C9—C10	1.517 (5)	C29—C30	1.382 (4)
C9—H9	1.0000	C29—H29	0.9500
C10—C15	1.383 (5)	C30—H30	0.9500
C10—C11	1.394 (5)	C31—H31A	0.9800
C11—C12	1.391 (5)	C31—H31B	0.9800
C11—H11	0.9500	C31—H31C	0.9800
C28—O2—C31	118.2 (3)	C13—C14—H14	119.7
C16—N1—N2	114.1 (2)	C14—C15—C10	120.8 (4)
C16—N1—C9	124.8 (3)	C14—C15—H15	119.6
N2—N1—C9	120.7 (2)	C10—C15—H15	119.6
C17—N2—N1	104.7 (2)	N1—C16—N3	101.8 (3)
C17—N3—C16	109.3 (2)	N1—C16—S1	128.7 (2)
C17—N3—N4	123.9 (2)	N3—C16—S1	129.5 (2)
C16—N3—N4	125.4 (2)	N2—C17—N3	110.0 (3)
C24—N4—N3	112.8 (2)	N2—C17—C18	122.7 (3)
C2—C1—C6	120.9 (4)	N3—C17—C18	127.3 (3)
C2—C1—H1	119.6	C19—C18—C23	119.2 (3)
C6—C1—H1	119.6	C19—C18—C17	123.6 (3)
C1—C2—C3	120.5 (4)	C23—C18—C17	117.1 (3)
C1—C2—H2	119.8	C20—C19—C18	119.9 (3)
C3—C2—H2	119.8	C20—C19—H19	120.0
C4—C3—C2	119.8 (4)	C18—C19—H19	120.0
C4—C3—H3	120.1	C19—C20—C21	120.8 (3)
C2—C3—H3	120.1	C19—C20—H20	119.6
C3—C4—C5	120.0 (4)	C21—C20—H20	119.6
C3—C4—H4	120.0	C20—C21—C22	119.5 (3)
C5—C4—H4	120.0	C20—C21—H21	120.2
C6—C5—C4	121.0 (4)	C22—C21—H21	120.2
C6—C5—H5	119.5	C23—C22—C21	120.4 (3)
C4—C5—H5	119.5	C23—C22—H22	119.8
C5—C6—C1	117.8 (4)	C21—C22—H22	119.8
C5—C6—C7	123.2 (3)	C22—C23—C18	120.1 (3)
C1—C6—C7	119.0 (3)	C22—C23—H23	120.0
O1—C7—C6	121.1 (3)	C18—C23—H23	120.0
O1—C7—C8	120.7 (3)	N4—C24—C25	121.2 (3)
C6—C7—C8	118.2 (3)	N4—C24—H24	119.4
C7—C8—C9	114.3 (3)	C25—C24—H24	119.4
C7—C8—H8A	108.7	C30—C25—C26	118.6 (3)
C9—C8—H8A	108.7	C30—C25—C24	123.0 (3)
C7—C8—H8B	108.7	C26—C25—C24	118.4 (3)
C9—C8—H8B	108.7	C27—C26—C25	120.6 (3)
H8A—C8—H8B	107.6	C27—C26—H26	119.7
N1—C9—C10	111.2 (3)	C25—C26—H26	119.7
N1—C9—C8	109.3 (3)	C26—C27—C28	119.7 (3)
C10—C9—C8	110.5 (3)	C26—C27—H27	120.2
N1—C9—H9	108.6	C28—C27—H27	120.2
C10—C9—H9	108.6	O2—C28—C29	124.7 (3)
C8—C9—H9	108.6	O2—C28—C27	114.8 (3)
C15—C10—C11	118.8 (3)	C29—C28—C27	120.6 (3)
C15—C10—C9	119.4 (3)	C30—C29—C28	118.9 (3)
C11—C10—C9	121.8 (3)	C30—C29—H29	120.6
C12—C11—C10	120.0 (3)	C28—C29—H29	120.6
C12—C11—H11	120.0	C29—C30—C25	121.7 (3)
C10—C11—H11	120.0	C29—C30—H30	119.2
C13—C12—C11	120.8 (4)	C25—C30—H30	119.2
C13—C12—H12	119.6	O2—C31—H31A	109.5
C11—C12—H12	119.6	O2—C31—H31B	109.5
C12—C13—C14	119.0 (4)	H31A—C31—H31B	109.5
C12—C13—H13	120.5	O2—C31—H31C	109.5
C14—C13—H13	120.5	H31A—C31—H31C	109.5
C15—C14—C13	120.7 (4)	H31B—C31—H31C	109.5
C15—C14—H14	119.7
C16—N1—N2—C17	0.1 (3)	C9—N1—C16—S1	−3.3 (5)
C9—N1—N2—C17	−172.9 (3)	C17—N3—C16—N1	−3.1 (3)
C17—N3—N4—C24	142.3 (3)	N4—N3—C16—N1	−169.9 (3)
C16—N3—N4—C24	−52.7 (4)	C17—N3—C16—S1	174.8 (2)
C6—C1—C2—C3	0.5 (6)	N4—N3—C16—S1	7.9 (5)
C1—C2—C3—C4	0.0 (6)	N1—N2—C17—N3	−2.2 (3)
C2—C3—C4—C5	−0.7 (6)	N1—N2—C17—C18	179.3 (3)
C3—C4—C5—C6	0.9 (6)	C16—N3—C17—N2	3.4 (3)
C4—C5—C6—C1	−0.4 (5)	N4—N3—C17—N2	170.6 (3)
C4—C5—C6—C7	−179.4 (3)	C16—N3—C17—C18	−178.1 (3)
C2—C1—C6—C5	−0.3 (5)	N4—N3—C17—C18	−11.0 (4)
C2—C1—C6—C7	178.8 (3)	N2—C17—C18—C19	153.5 (3)
C5—C6—C7—O1	179.6 (3)	N3—C17—C18—C19	−24.8 (5)
C1—C6—C7—O1	0.6 (5)	N2—C17—C18—C23	−24.6 (4)
C5—C6—C7—C8	−1.2 (5)	N3—C17—C18—C23	157.1 (3)
C1—C6—C7—C8	179.8 (3)	C23—C18—C19—C20	−0.9 (4)
O1—C7—C8—C9	−18.3 (5)	C17—C18—C19—C20	−179.0 (3)
C6—C7—C8—C9	162.5 (3)	C18—C19—C20—C21	0.0 (5)
C16—N1—C9—C10	−71.5 (4)	C19—C20—C21—C22	0.9 (5)
N2—N1—C9—C10	100.8 (3)	C20—C21—C22—C23	−0.9 (5)
C16—N1—C9—C8	166.2 (3)	C21—C22—C23—C18	0.0 (4)
N2—N1—C9—C8	−21.5 (4)	C19—C18—C23—C22	0.9 (4)
C7—C8—C9—N1	−62.6 (4)	C17—C18—C23—C22	179.1 (3)
C7—C8—C9—C10	174.7 (3)	N3—N4—C24—C25	174.5 (3)
N1—C9—C10—C15	141.4 (3)	N4—C24—C25—C30	−14.1 (5)
C8—C9—C10—C15	−97.0 (4)	N4—C24—C25—C26	166.2 (3)
N1—C9—C10—C11	−41.5 (4)	C30—C25—C26—C27	2.1 (5)
C8—C9—C10—C11	80.0 (4)	C24—C25—C26—C27	−178.1 (3)
C15—C10—C11—C12	0.0 (5)	C25—C26—C27—C28	−0.6 (5)
C9—C10—C11—C12	−177.1 (3)	C31—O2—C28—C29	−7.6 (4)
C10—C11—C12—C13	1.6 (6)	C31—O2—C28—C27	172.3 (3)
C11—C12—C13—C14	−1.3 (6)	C26—C27—C28—O2	178.8 (3)
C12—C13—C14—C15	−0.6 (6)	C26—C27—C28—C29	−1.3 (5)
C13—C14—C15—C10	2.1 (6)	O2—C28—C29—C30	−178.6 (3)
C11—C10—C15—C14	−1.8 (6)	C27—C28—C29—C30	1.6 (5)
C9—C10—C15—C14	175.3 (4)	C28—C29—C30—C25	0.1 (5)
N2—N1—C16—N3	1.8 (3)	C26—C25—C30—C29	−1.9 (5)
C9—N1—C16—N3	174.5 (3)	C24—C25—C30—C29	178.4 (3)
N2—N1—C16—S1	−176.0 (2)