rac-3-{4-[(Furan-2-ylmethyl-idene)-amino]-3-methyl-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(23)H(20)N(4)O(2)S, the triazole ring forms dihedral angles of 150.3 (2), 77.3 (2) and 77.6 (2)°, respectively, with the furan ring and the phenyl rings. The furan ring is almost perpendicular to the central phenyl ring, making a dihedral angle of 86.0 (3)°.

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

C23H20N4O2S

M = 416.50

Monoclinic,

a = 8.154 (3) Å

b = 21.194 (6) Å

c = 12.878 (4) Å

β = 107.965 (5)°

V = 2117.0 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 113 K

0.24 × 0.20 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.958, T max = 0.979

26979 measured reflections

5030 independent reflections

4229 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.106

S = 1.07

5030 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.18 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/S1600536811035185/zs2141sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035185/zs2141Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035185/zs2141Isup3.cml

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

C23H20N4O2S	F(000) = 872
Mr = 416.50	Dx = 1.307 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7435 reflections
a = 8.154 (3) Å	θ = 1.7–27.9°
b = 21.194 (6) Å	µ = 0.18 mm−1
c = 12.878 (4) Å	T = 113 K
β = 107.965 (5)°	Prism, colorless
V = 2117.0 (12) Å3	0.24 × 0.20 × 0.12 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	5030 independent reflections
Radiation source: rotating anode	4229 reflections with I > 2σ(I)
multilayer	Rint = 0.043
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 1.9°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −27→27
Tmin = 0.958, Tmax = 0.979	l = −16→16
26979 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0597P)2 + 0.0507P] where P = (Fo2 + 2Fc2)/3
5030 reflections	(Δ/σ)max = 0.001
272 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	1.09278 (4)	0.678722 (17)	0.64588 (3)	0.03095 (11)
O1	0.74128 (14)	0.76825 (5)	0.75402 (7)	0.0366 (2)
O2	0.80256 (13)	0.49556 (5)	0.33988 (7)	0.0370 (2)
N1	0.89702 (13)	0.64352 (5)	0.77200 (8)	0.0210 (2)
N2	0.76948 (13)	0.60222 (5)	0.77821 (8)	0.0258 (2)
N3	0.82733 (13)	0.59160 (5)	0.62302 (8)	0.0231 (2)
N4	0.81208 (14)	0.55961 (5)	0.52572 (8)	0.0287 (3)
C1	0.93901 (15)	0.63862 (6)	0.67870 (9)	0.0215 (3)
C2	0.73025 (17)	0.57115 (6)	0.68692 (10)	0.0265 (3)
C3	0.98664 (16)	0.68280 (6)	0.86642 (9)	0.0231 (3)
H3	1.0421	0.7187	0.8396	0.028*
C4	0.85808 (17)	0.71013 (6)	0.91857 (10)	0.0272 (3)
H4A	0.7942	0.6751	0.9394	0.033*
H4B	0.9219	0.7329	0.9861	0.033*
C5	0.73023 (17)	0.75493 (6)	0.84367 (10)	0.0265 (3)
C6	0.59252 (16)	0.78340 (6)	0.88329 (10)	0.0254 (3)
C7	0.45618 (19)	0.81411 (6)	0.80761 (12)	0.0339 (3)
H7	0.4509	0.8154	0.7329	0.041*
C8	0.3287 (2)	0.84270 (7)	0.84094 (13)	0.0431 (4)
H8	0.2349	0.8630	0.7889	0.052*
C9	0.3374 (2)	0.84195 (7)	0.95004 (13)	0.0414 (4)
H9	0.2509	0.8625	0.9729	0.050*
C10	0.47170 (19)	0.81126 (6)	1.02590 (12)	0.0327 (3)
H10	0.4766	0.8104	1.1005	0.039*
C11	0.59897 (17)	0.78178 (6)	0.99299 (10)	0.0275 (3)
H11	0.6907	0.7605	1.0450	0.033*
C12	1.12820 (16)	0.64429 (6)	0.94503 (9)	0.0234 (3)
C13	1.08906 (17)	0.59523 (6)	1.00540 (10)	0.0288 (3)
H13	0.9722	0.5870	1.0001	0.035*
C14	1.21854 (18)	0.55835 (7)	1.07314 (11)	0.0325 (3)
H14	1.1904	0.5249	1.1137	0.039*
C15	1.38920 (18)	0.57036 (7)	1.08172 (11)	0.0373 (3)
H15	1.4783	0.5452	1.1281	0.045*
C16	1.42945 (18)	0.61911 (7)	1.02258 (12)	0.0401 (4)
H16	1.5466	0.6274	1.0287	0.048*
C17	1.30023 (17)	0.65601 (7)	0.95437 (11)	0.0314 (3)
H17	1.3291	0.6894	0.9139	0.038*
C18	0.86294 (17)	0.58860 (7)	0.45364 (10)	0.0296 (3)
H18	0.9078	0.6302	0.4672	0.036*
C19	0.85153 (17)	0.55772 (7)	0.35217 (10)	0.0309 (3)
C20	0.87864 (18)	0.57953 (8)	0.26002 (11)	0.0385 (3)
H20	0.9137	0.6209	0.2477	0.046*
C21	0.84408 (19)	0.52813 (8)	0.18528 (12)	0.0420 (4)
H21	0.8514	0.5284	0.1131	0.050*
C22	0.79925 (19)	0.47929 (8)	0.23657 (11)	0.0410 (4)
H22	0.7691	0.4387	0.2053	0.049*
C23	0.5960 (2)	0.52161 (7)	0.65264 (11)	0.0430 (4)
H23A	0.5505	0.5122	0.7130	0.064*
H23B	0.6465	0.4833	0.6326	0.064*
H23C	0.5023	0.5366	0.5896	0.064*

	U11	U22	U33	U12	U13	U23
S1	0.02698 (19)	0.0442 (2)	0.02233 (18)	−0.00676 (14)	0.00865 (14)	0.00319 (14)
O1	0.0485 (6)	0.0389 (5)	0.0253 (5)	0.0118 (5)	0.0157 (5)	0.0049 (4)
O2	0.0429 (6)	0.0387 (5)	0.0242 (5)	0.0133 (5)	0.0029 (4)	−0.0078 (4)
N1	0.0226 (5)	0.0225 (5)	0.0178 (5)	−0.0028 (4)	0.0064 (4)	−0.0018 (4)
N2	0.0259 (6)	0.0297 (6)	0.0211 (5)	−0.0072 (4)	0.0063 (4)	0.0013 (4)
N3	0.0281 (6)	0.0235 (5)	0.0160 (5)	−0.0001 (4)	0.0043 (4)	−0.0017 (4)
N4	0.0341 (6)	0.0309 (6)	0.0172 (5)	0.0061 (5)	0.0023 (4)	−0.0055 (4)
C1	0.0229 (6)	0.0241 (6)	0.0166 (6)	0.0029 (5)	0.0046 (5)	0.0011 (5)
C2	0.0301 (7)	0.0274 (6)	0.0192 (6)	−0.0050 (5)	0.0035 (5)	0.0027 (5)
C3	0.0271 (7)	0.0229 (6)	0.0183 (6)	−0.0037 (5)	0.0055 (5)	−0.0036 (5)
C4	0.0339 (7)	0.0273 (7)	0.0195 (6)	0.0040 (6)	0.0069 (5)	−0.0033 (5)
C5	0.0323 (7)	0.0236 (6)	0.0222 (6)	−0.0004 (5)	0.0063 (5)	−0.0041 (5)
C6	0.0275 (7)	0.0218 (6)	0.0263 (6)	−0.0025 (5)	0.0074 (5)	−0.0016 (5)
C7	0.0347 (8)	0.0358 (7)	0.0308 (7)	0.0035 (6)	0.0097 (6)	0.0065 (6)
C8	0.0360 (8)	0.0490 (9)	0.0460 (9)	0.0126 (7)	0.0153 (7)	0.0151 (7)
C9	0.0392 (9)	0.0420 (8)	0.0509 (9)	0.0085 (7)	0.0255 (8)	0.0075 (7)
C10	0.0379 (8)	0.0320 (7)	0.0327 (7)	−0.0012 (6)	0.0175 (6)	−0.0010 (6)
C11	0.0304 (7)	0.0251 (6)	0.0263 (6)	−0.0038 (5)	0.0078 (5)	−0.0023 (5)
C12	0.0257 (6)	0.0235 (6)	0.0197 (6)	−0.0018 (5)	0.0051 (5)	−0.0053 (5)
C13	0.0259 (7)	0.0316 (7)	0.0276 (7)	−0.0014 (5)	0.0064 (5)	0.0006 (5)
C14	0.0349 (8)	0.0333 (7)	0.0270 (7)	0.0004 (6)	0.0059 (6)	0.0043 (6)
C15	0.0300 (7)	0.0457 (8)	0.0307 (7)	0.0070 (6)	0.0013 (6)	0.0049 (6)
C16	0.0231 (7)	0.0558 (10)	0.0374 (8)	−0.0030 (7)	0.0035 (6)	0.0030 (7)
C17	0.0293 (7)	0.0355 (7)	0.0268 (7)	−0.0071 (6)	0.0052 (6)	−0.0001 (6)
C18	0.0312 (7)	0.0346 (7)	0.0203 (6)	0.0082 (6)	0.0038 (5)	−0.0023 (5)
C19	0.0271 (7)	0.0390 (7)	0.0233 (6)	0.0104 (6)	0.0026 (5)	−0.0044 (6)
C20	0.0343 (8)	0.0556 (9)	0.0252 (7)	0.0017 (7)	0.0086 (6)	−0.0073 (6)
C21	0.0342 (8)	0.0678 (11)	0.0231 (7)	0.0116 (8)	0.0073 (6)	−0.0102 (7)
C22	0.0372 (8)	0.0515 (9)	0.0266 (7)	0.0192 (7)	−0.0012 (6)	−0.0157 (7)
C23	0.0523 (10)	0.0433 (9)	0.0259 (7)	−0.0241 (7)	0.0012 (7)	0.0018 (6)

S1—C1	1.6734 (13)	C9—H9	0.9500
O1—C5	1.2185 (15)	C10—C11	1.3851 (19)
O2—C22	1.3666 (16)	C10—H10	0.9500
O2—C19	1.3715 (18)	C11—H11	0.9500
N1—C1	1.3511 (15)	C12—C17	1.3927 (18)
N1—N2	1.3803 (14)	C12—C13	1.3930 (18)
N1—C3	1.4688 (15)	C13—C14	1.3852 (19)
N2—C2	1.2984 (16)	C13—H13	0.9500
N3—C2	1.3760 (16)	C14—C15	1.385 (2)
N3—C1	1.3906 (15)	C14—H14	0.9500
N3—N4	1.3961 (14)	C15—C16	1.382 (2)
N4—C18	1.2840 (17)	C15—H15	0.9500
C2—C23	1.4823 (18)	C16—C17	1.387 (2)
C3—C12	1.5174 (17)	C16—H16	0.9500
C3—C4	1.5232 (17)	C17—H17	0.9500
C3—H3	1.0000	C18—C19	1.4386 (18)
C4—C5	1.5160 (18)	C18—H18	0.9500
C4—H4A	0.9900	C19—C20	1.354 (2)
C4—H4B	0.9900	C20—C21	1.423 (2)
C5—C6	1.4961 (18)	C20—H20	0.9500
C6—C7	1.3932 (19)	C21—C22	1.338 (2)
C6—C11	1.3978 (17)	C21—H21	0.9500
C7—C8	1.381 (2)	C22—H22	0.9500
C7—H7	0.9500	C23—H23A	0.9800
C8—C9	1.385 (2)	C23—H23B	0.9800
C8—H8	0.9500	C23—H23C	0.9800
C9—C10	1.385 (2)
C22—O2—C19	105.81 (11)	C11—C10—H10	120.0
C1—N1—N2	113.88 (10)	C10—C11—C6	120.00 (13)
C1—N1—C3	125.58 (10)	C10—C11—H11	120.0
N2—N1—C3	120.19 (9)	C6—C11—H11	120.0
C2—N2—N1	104.40 (10)	C17—C12—C13	118.88 (12)
C2—N3—C1	108.86 (10)	C17—C12—C3	120.02 (11)
C2—N3—N4	118.39 (10)	C13—C12—C3	121.05 (11)
C1—N3—N4	132.36 (10)	C14—C13—C12	120.76 (13)
C18—N4—N3	117.20 (11)	C14—C13—H13	119.6
N1—C1—N3	102.03 (10)	C12—C13—H13	119.6
N1—C1—S1	126.93 (9)	C15—C14—C13	119.89 (13)
N3—C1—S1	131.01 (9)	C15—C14—H14	120.1
N2—C2—N3	110.81 (11)	C13—C14—H14	120.1
N2—C2—C23	125.59 (12)	C16—C15—C14	119.81 (13)
N3—C2—C23	123.58 (11)	C16—C15—H15	120.1
N1—C3—C12	109.22 (9)	C14—C15—H15	120.1
N1—C3—C4	110.25 (10)	C15—C16—C17	120.51 (13)
C12—C3—C4	113.31 (10)	C15—C16—H16	119.7
N1—C3—H3	108.0	C17—C16—H16	119.7
C12—C3—H3	108.0	C16—C17—C12	120.16 (13)
C4—C3—H3	108.0	C16—C17—H17	119.9
C5—C4—C3	112.91 (10)	C12—C17—H17	119.9
C5—C4—H4A	109.0	N4—C18—C19	119.61 (13)
C3—C4—H4A	109.0	N4—C18—H18	120.2
C5—C4—H4B	109.0	C19—C18—H18	120.2
C3—C4—H4B	109.0	C20—C19—O2	110.32 (12)
H4A—C4—H4B	107.8	C20—C19—C18	131.19 (14)
O1—C5—C6	120.81 (12)	O2—C19—C18	118.48 (12)
O1—C5—C4	120.71 (12)	C19—C20—C21	106.23 (14)
C6—C5—C4	118.47 (11)	C19—C20—H20	126.9
C7—C6—C11	119.45 (12)	C21—C20—H20	126.9
C7—C6—C5	118.08 (11)	C22—C21—C20	106.60 (13)
C11—C6—C5	122.44 (12)	C22—C21—H21	126.7
C8—C7—C6	120.15 (13)	C20—C21—H21	126.7
C8—C7—H7	119.9	C21—C22—O2	111.03 (13)
C6—C7—H7	119.9	C21—C22—H22	124.5
C7—C8—C9	120.18 (14)	O2—C22—H22	124.5
C7—C8—H8	119.9	C2—C23—H23A	109.5
C9—C8—H8	119.9	C2—C23—H23B	109.5
C10—C9—C8	120.17 (13)	H23A—C23—H23B	109.5
C10—C9—H9	119.9	C2—C23—H23C	109.5
C8—C9—H9	119.9	H23A—C23—H23C	109.5
C9—C10—C11	120.03 (13)	H23B—C23—H23C	109.5
C9—C10—H10	120.0
C1—N1—N2—C2	−0.35 (13)	C11—C6—C7—C8	0.0 (2)
C3—N1—N2—C2	−173.97 (11)	C5—C6—C7—C8	−178.09 (13)
C2—N3—N4—C18	160.90 (12)	C6—C7—C8—C9	1.1 (2)
C1—N3—N4—C18	−27.24 (19)	C7—C8—C9—C10	−1.5 (2)
N2—N1—C1—N3	0.93 (13)	C8—C9—C10—C11	0.7 (2)
C3—N1—C1—N3	174.15 (10)	C9—C10—C11—C6	0.5 (2)
N2—N1—C1—S1	−177.18 (9)	C7—C6—C11—C10	−0.84 (19)
C3—N1—C1—S1	−3.96 (17)	C5—C6—C11—C10	177.21 (12)
C2—N3—C1—N1	−1.14 (13)	N1—C3—C12—C17	106.97 (13)
N4—N3—C1—N1	−173.59 (11)	C4—C3—C12—C17	−129.70 (12)
C2—N3—C1—S1	176.86 (10)	N1—C3—C12—C13	−70.35 (14)
N4—N3—C1—S1	4.4 (2)	C4—C3—C12—C13	52.98 (15)
N1—N2—C2—N3	−0.43 (14)	C17—C12—C13—C14	−0.41 (18)
N1—N2—C2—C23	−178.64 (13)	C3—C12—C13—C14	176.94 (11)
C1—N3—C2—N2	1.04 (15)	C12—C13—C14—C15	0.3 (2)
N4—N3—C2—N2	174.70 (10)	C13—C14—C15—C16	0.0 (2)
C1—N3—C2—C23	179.29 (12)	C14—C15—C16—C17	−0.2 (2)
N4—N3—C2—C23	−7.05 (18)	C15—C16—C17—C12	0.1 (2)
C1—N1—C3—C12	−90.83 (13)	C13—C12—C17—C16	0.19 (19)
N2—N1—C3—C12	81.99 (13)	C3—C12—C17—C16	−177.19 (12)
C1—N1—C3—C4	144.04 (11)	N3—N4—C18—C19	179.51 (11)
N2—N1—C3—C4	−43.14 (14)	C22—O2—C19—C20	−0.25 (15)
N1—C3—C4—C5	−64.25 (13)	C22—O2—C19—C18	178.72 (11)
C12—C3—C4—C5	172.98 (10)	N4—C18—C19—C20	172.22 (14)
C3—C4—C5—O1	−3.40 (17)	N4—C18—C19—O2	−6.51 (19)
C3—C4—C5—C6	177.83 (11)	O2—C19—C20—C21	0.22 (16)
O1—C5—C6—C7	13.79 (19)	C18—C19—C20—C21	−178.59 (14)
C4—C5—C6—C7	−167.44 (12)	C19—C20—C21—C22	−0.10 (16)
O1—C5—C6—C11	−164.29 (12)	C20—C21—C22—O2	−0.06 (17)
C4—C5—C6—C11	14.49 (18)	C19—O2—C22—C21	0.19 (15)