4-(4-Chloro­phenyl)-3-(furan-2-yl)-1H-1,2,4-triazole-5(4H)-thione

The title mol­ecule, C₁₂H₈ClN₃OS, is not planar. The benzene and furan rings make dihedral angles of 78.4 (1) and 5.6 (1)° with the mean plane of the central triazole ring. The crystal structure is stabilized by N—H...S, C—H...Cl, C—H...N, C—H...π and π–π interactions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.033
• wR factor = 0.098
• Data-to-parameter ratio = 20.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       3.00 Sigma
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   C1       =       5.72 su
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6     ..  CG1      =       2.99 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12    ..  CG2      =       3.09 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: EVALCCD (Duisenberg, 2003); data reduction: EVALCCD; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

4-(4-Chlorophenyl)-3-(furan-2-yl)-1H-1,2,4-triazole-5(4H)-thione

Crystal data

C12H8ClN3OS	Z = 2
Mr = 277.73	F(000) = 284
Triclinic, P1	Dx = 1.499 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.524 (5) Å	Cell parameters from 78 reflections
b = 8.640 (5) Å	θ = 6–20°
c = 9.307 (5) Å	µ = 0.47 mm^−1
α = 91.426 (5)°	T = 100 K
β = 90.250 (5)°	Prism, colorless
γ = 116.059 (5)°	0.23 × 0.15 × 0.07 mm
V = 615.5 (6) Å^3

Data collection

Bruker–Nonius KappaCCD diffractometer	3274 independent reflections
Radiation source: fine-focus sealed tube	2673 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 9 pixels mm^-1	θmax = 29.0°, θmin = 2.8°
ω scans (per frame) with 2.0° and 80 s per frame	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→11
Tmin = 0.900, Tmax = 0.968	l = −12→12
17300 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.053P)^2 + 0.1559P] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max = 0.001
3274 reflections	Δρmax = 0.43 e Å^−3
164 parameters	Δρmin = −0.34 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (4)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^{2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 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
Cl1	0.24926 (5)	0.28710 (6)	0.54297 (5)	0.0221 (1)
S1	0.73723 (5)	−0.06080 (5)	0.86255 (4)	0.0150 (1)
O1	1.25470 (15)	0.71668 (15)	0.82711 (13)	0.0158 (3)
N1	0.88284 (17)	0.28469 (17)	0.80635 (14)	0.0107 (3)
N2	1.05521 (17)	0.20964 (17)	0.92167 (14)	0.0122 (4)
N3	1.14754 (17)	0.38461 (17)	0.90714 (14)	0.0119 (3)
C1	0.8929 (2)	0.1433 (2)	0.86417 (17)	0.0118 (4)
C2	1.03994 (19)	0.42718 (19)	0.83586 (16)	0.0104 (4)
C3	1.08480 (19)	0.6018 (2)	0.79432 (16)	0.0109 (4)
C4	1.2724 (2)	0.8746 (2)	0.78527 (18)	0.0161 (4)
C5	1.1205 (2)	0.8616 (2)	0.72812 (17)	0.0159 (4)
C6	0.9981 (2)	0.6844 (2)	0.73417 (17)	0.0145 (4)
C7	0.72759 (19)	0.28256 (19)	0.74118 (17)	0.0109 (4)
C8	0.6261 (2)	0.3385 (2)	0.82327 (17)	0.0139 (4)
C9	0.4795 (2)	0.3427 (2)	0.76078 (18)	0.0150 (4)
C10	0.4369 (2)	0.2865 (2)	0.61864 (18)	0.0142 (4)
C11	0.5365 (2)	0.2285 (2)	0.53635 (18)	0.0166 (5)
C12	0.6855 (2)	0.2277 (2)	0.59868 (17)	0.0145 (4)
H2	1.09730	0.14820	0.96360	0.0150*
H4	1.37470	0.97660	0.79480	0.0190*
H5	1.10010	0.95070	0.69200	0.0190*
H6	0.88200	0.63520	0.70310	0.0170*
H8	0.65570	0.37290	0.91900	0.0170*
H9	0.41130	0.38240	0.81330	0.0180*
H11	0.50480	0.19090	0.44150	0.0200*
H12	0.75560	0.19090	0.54540	0.0170*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0151 (2)	0.0280 (2)	0.0246 (2)	0.0108 (2)	−0.0075 (2)	0.0046 (2)
S1	0.0120 (2)	0.0096 (2)	0.0217 (2)	0.0033 (2)	−0.0047 (2)	0.0007 (1)
O1	0.0111 (5)	0.0112 (5)	0.0219 (6)	0.0018 (4)	−0.0036 (5)	0.0023 (4)
N1	0.0086 (6)	0.0106 (6)	0.0125 (6)	0.0039 (5)	−0.0013 (5)	0.0002 (5)
N2	0.0109 (6)	0.0097 (6)	0.0165 (7)	0.0049 (5)	−0.0019 (5)	0.0018 (5)
N3	0.0110 (6)	0.0105 (6)	0.0136 (6)	0.0042 (5)	−0.0002 (5)	0.0005 (5)
C1	0.0115 (7)	0.0131 (7)	0.0120 (7)	0.0067 (6)	−0.0002 (6)	−0.0005 (6)
C2	0.0084 (7)	0.0120 (7)	0.0104 (7)	0.0042 (6)	0.0000 (5)	−0.0008 (5)
C3	0.0087 (7)	0.0111 (7)	0.0112 (7)	0.0028 (6)	0.0001 (5)	−0.0002 (6)
C4	0.0173 (8)	0.0097 (7)	0.0183 (8)	0.0032 (6)	0.0008 (6)	0.0025 (6)
C5	0.0193 (8)	0.0134 (7)	0.0158 (8)	0.0078 (7)	0.0028 (6)	0.0038 (6)
C6	0.0117 (7)	0.0150 (8)	0.0161 (8)	0.0051 (6)	0.0000 (6)	0.0026 (6)
C7	0.0084 (7)	0.0095 (7)	0.0144 (7)	0.0035 (6)	−0.0013 (6)	0.0023 (6)
C8	0.0114 (7)	0.0167 (8)	0.0129 (7)	0.0057 (6)	−0.0017 (6)	−0.0021 (6)
C9	0.0113 (7)	0.0176 (8)	0.0175 (8)	0.0076 (6)	0.0001 (6)	−0.0005 (6)
C10	0.0094 (7)	0.0131 (7)	0.0183 (8)	0.0033 (6)	−0.0048 (6)	0.0039 (6)
C11	0.0187 (8)	0.0176 (8)	0.0125 (8)	0.0071 (7)	−0.0041 (6)	−0.0010 (6)
C12	0.0143 (7)	0.0156 (8)	0.0144 (8)	0.0074 (6)	−0.0010 (6)	−0.0014 (6)

Geometric parameters (Å, º)

Cl1—C10	1.747 (2)	C5—C6	1.427 (2)
S1—C1	1.6773 (19)	C7—C12	1.388 (2)
O1—C3	1.376 (2)	C7—C8	1.386 (3)
O1—C4	1.372 (2)	C8—C9	1.391 (3)
N1—C1	1.383 (2)	C9—C10	1.388 (2)
N1—C2	1.384 (2)	C10—C11	1.385 (3)
N1—C7	1.446 (2)	C11—C12	1.397 (3)
N2—N3	1.374 (2)	C4—H4	0.93
N2—C1	1.346 (2)	C5—H5	0.93
N3—C2	1.311 (2)	C6—H6	0.93
N2—H2	0.86	C8—H8	0.93
C2—C3	1.448 (2)	C9—H9	0.93
C3—C6	1.360 (3)	C11—H11	0.93
C4—C5	1.355 (3)	C12—H12	0.93
Cl1···C6^i	3.406 (3)	C7···C6	3.218 (3)
Cl1···H5^ii	2.9929	C8···N3^iv	3.368 (3)
Cl1···H6^i	2.7679	C8···C6	3.390 (3)
S1···N2^iii	3.304 (2)	C8···C3	3.572 (3)
S1···C4^iv	3.632 (3)	C9···N3^vii	3.302 (3)
S1···H2^iii	2.4808	C10···C4^ii	3.598 (3)
O1···N3	2.726 (2)	C1···H2^iii	3.0503
O1···H8^iv	2.7130	C4···H11^viii	3.0498
N1···N3	2.224 (3)	C5···H12^viii	2.8615
N2···N1	2.142 (2)	C7···H6	2.7705
N2···S1^iii	3.304 (2)	C7···H4^ii	3.0623
N2···C6^iv	3.397 (3)	C8···H6	2.7985
N3···C3^iv	3.449 (3)	C8···H4^ii	2.9165
N3···O1	2.726 (2)	C9···H4^ii	2.9109
N3···N1	2.224 (3)	C10···H4^ii	3.0195
N3···C9^v	3.302 (3)	H2···S1^iii	2.4808
N3···C8^iv	3.368 (3)	H2···C1^iii	3.0503
N2···H9^v	2.9291	H2···H2^iii	2.4764
N3···H9^v	2.4232	H4···C7^vi	3.0623
N3···H8^iv	2.5575	H4···C8^vi	2.9165
C1···C4^iv	3.540 (3)	H4···C9^vi	2.9109
C2···C2^iv	3.459 (3)	H4···C10^vi	3.0195
C2···C3^iv	3.589 (3)	H5···Cl1^vi	2.9929
C3···C8	3.572 (3)	H6···C7	2.7705
C3···N3^iv	3.449 (3)	H6···C8	2.7985
C3···C2^iv	3.589 (3)	H6···Cl1^i	2.7679
C4···S1^iv	3.632 (3)	H8···O1^iv	2.7130
C4···C10^vi	3.598 (3)	H8···N3^iv	2.5575
C4···C1^iv	3.540 (3)	H9···N2^vii	2.9291
C6···N2^iv	3.397 (3)	H9···N3^vii	2.4232
C6···C8	3.390 (3)	H11···C4^viii	3.0498
C6···Cl1^i	3.406 (3)	H12···C5^viii	2.8615
C6···C7	3.218 (3)
C3—O1—C4	106.04 (14)	N1—C7—C12	119.65 (15)
C1—N1—C2	107.65 (14)	C7—C8—C9	119.23 (15)
C1—N1—C7	124.81 (14)	C8—C9—C10	118.82 (16)
C2—N1—C7	127.24 (13)	Cl1—C10—C11	119.36 (13)
N3—N2—C1	113.82 (14)	Cl1—C10—C9	118.34 (14)
N2—N3—C2	103.93 (13)	C9—C10—C11	122.30 (17)
N3—N2—H2	123.10	C10—C11—C12	118.69 (15)
C1—N2—H2	123.09	C7—C12—C11	119.11 (16)
N1—C1—N2	103.43 (13)	O1—C4—H4	124.64
S1—C1—N1	127.51 (14)	C5—C4—H4	124.65
S1—C1—N2	129.05 (13)	C4—C5—H5	126.72
N1—C2—N3	111.16 (13)	C6—C5—H5	126.80
N1—C2—C3	125.81 (15)	C3—C6—H6	126.82
N3—C2—C3	123.03 (15)	C5—C6—H6	126.79
O1—C3—C2	113.89 (14)	C7—C8—H8	120.37
C2—C3—C6	135.68 (16)	C9—C8—H8	120.39
O1—C3—C6	110.38 (14)	C8—C9—H9	120.58
O1—C4—C5	110.71 (14)	C10—C9—H9	120.60
C4—C5—C6	106.48 (15)	C10—C11—H11	120.64
C3—C6—C5	106.40 (15)	C12—C11—H11	120.67
C8—C7—C12	121.83 (16)	C7—C12—H12	120.45
N1—C7—C8	118.51 (14)	C11—C12—H12	120.44
C4—O1—C3—C6	−0.14 (18)	N2—N3—C2—C3	−179.09 (14)
C4—O1—C3—C2	−178.01 (13)	N3—C2—C3—O1	4.5 (2)
C3—O1—C4—C5	−0.02 (19)	N1—C2—C3—C6	7.9 (3)
C2—N1—C1—S1	178.54 (13)	N1—C2—C3—O1	−175.00 (14)
C7—N1—C1—N2	−175.07 (14)	N3—C2—C3—C6	−172.65 (18)
C1—N1—C2—N3	0.38 (18)	C2—C3—C6—C5	177.44 (17)
C7—N1—C2—C3	−6.3 (3)	O1—C3—C6—C5	0.23 (18)
C7—N1—C2—N3	174.20 (14)	O1—C4—C5—C6	0.14 (19)
C1—N1—C2—C3	179.92 (17)	C4—C5—C6—C3	−0.22 (19)
C2—N1—C7—C12	104.28 (18)	C12—C7—C8—C9	−1.1 (2)
C1—N1—C7—C12	−82.9 (2)	N1—C7—C12—C11	−179.12 (14)
C2—N1—C1—N2	−1.06 (17)	C8—C7—C12—C11	−0.2 (2)
C2—N1—C7—C8	−74.7 (2)	N1—C7—C8—C9	177.88 (14)
C7—N1—C1—S1	4.5 (2)	C7—C8—C9—C10	1.6 (2)
C1—N1—C7—C8	98.11 (18)	C8—C9—C10—C11	−0.9 (2)
C1—N2—N3—C2	−1.23 (18)	C8—C9—C10—Cl1	178.33 (12)
N3—N2—C1—N1	1.44 (18)	Cl1—C10—C11—C12	−179.57 (12)
N3—N2—C1—S1	−178.16 (13)	C9—C10—C11—C12	−0.4 (2)
N2—N3—C2—N1	0.47 (17)	C10—C11—C12—C7	0.9 (2)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y−1, z; (iii) −x+2, −y, −z+2; (iv) −x+2, −y+1, −z+2; (v) x+1, y, z; (vi) x+1, y+1, z; (vii) x−1, y, z; (viii) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1^iii	0.86	2.48	3.304 (2)	160
C6—H6···Cl1^i	0.93	2.77	3.406 (3)	127
C8—H8···N3^iv	0.93	2.56	3.368 (3)	146
C9—H9···N3^vii	0.93	2.42	3.302 (3)	158
C4—H4···Cg1^vi	0.93	2.71	3.529 (3)	147
C6—H6···Cg1	0.93	2.99	3.729 (3)	138
C12—H12···Cg2^viii	0.93	3.09	3.733 (3)	128

Symmetry codes: (i) −x+1, −y+1, −z+1; (iii) −x+2, −y, −z+2; (iv) −x+2, −y+1, −z+2; (vi) x+1, y+1, z; (vii) x−1, y, z; (viii) −x+2, −y+1, −z+1.