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

Öztürk, S.; Akkurt, M.; Cansız, A.; Koparır, M.; Şekerci, M.; Heinemann, F.W.

doi:10.1107/S1600536804003721

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

S. Öztürk, M. Akkurt, A. Cansız, M. Koparır, M. Şekerci and F. W. Heinemann

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804003721/ci6341sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804003721/ci6341Isup2.hkl Contains datablock I

CCDC reference: 236099

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (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

Computing details top

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 top

Crystal data top

C₁₂H₈ClN₃OS	Z = 2
M_r = 277.73	F(000) = 284
Triclinic, P1	D_x = 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) Å³

Data collection top

Bruker–Nonius KappaCCD diffractometer	3274 independent reflections
Radiation source: fine-focus sealed tube	2673 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 9 pixels mm^-1	θ_max = 29.0°, θ_min = 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
T_min = 0.900, T_max = 0.968	l = −12→12
17300 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.053P)² + 0.1559P] where P = (F_o² + 2F_c²)/3
S = 1.16	(Δ/σ)_max = 0.001
3274 reflections	Δρ_max = 0.43 e Å⁻³
164 parameters	Δρ_min = −0.34 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (4)

Special details top

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} ^F2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of} ^F2 > 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} ^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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

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···C6ⁱ	3.406 (3)	C7···C6	3.218 (3)
Cl1···H5ⁱⁱ	2.9929	C8···N3^iv	3.368 (3)
Cl1···H6ⁱ	2.7679	C8···C6	3.390 (3)
S1···N2ⁱⁱⁱ	3.304 (2)	C8···C3	3.572 (3)
S1···C4^iv	3.632 (3)	C9···N3^vii	3.302 (3)
S1···H2ⁱⁱⁱ	2.4808	C10···C4ⁱⁱ	3.598 (3)
O1···N3	2.726 (2)	C1···H2ⁱⁱⁱ	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···S1ⁱⁱⁱ	3.304 (2)	C7···H4ⁱⁱ	3.0623
N2···C6^iv	3.397 (3)	C8···H6	2.7985
N3···C3^iv	3.449 (3)	C8···H4ⁱⁱ	2.9165
N3···O1	2.726 (2)	C9···H4ⁱⁱ	2.9109
N3···N1	2.224 (3)	C10···H4ⁱⁱ	3.0195
N3···C9^v	3.302 (3)	H2···S1ⁱⁱⁱ	2.4808
N3···C8^iv	3.368 (3)	H2···C1ⁱⁱⁱ	3.0503
N2···H9^v	2.9291	H2···H2ⁱⁱⁱ	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···Cl1ⁱ	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···Cl1ⁱ	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) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1ⁱⁱⁱ	0.86	2.48	3.304 (2)	160
C6—H6···Cl1ⁱ	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.

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

Supporting information

Key indicators

checkCIF/PLATON results

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