2-Amino-4-(2,5-di­chloro­phenyl)-5-(1H-1,2,4-triazol-1-yl)-1,3-thia­zole

Shao, L.; Jin, Z.; Liu, J.-B.; Zhou, X.; Zhang, Q.; Hu, Y.; Fang, J.-X.

doi:10.1107/S160053680403079X

2-Amino-4-(2,5-dichlorophenyl)-5-(1H-1,2,4-triazol-1-yl)-1,3-thiazole

L. Shao, Z. Jin, J.-B. Liu, X. Zhou, Q. Zhang, Y. Hu and J.-X. Fang

The title compound, C₁₁H₇C₁₂N₅S, has been synthesized as a potent fungicidal agent and its crystal structure was determined. In the crystal structure there are weak intermolecular N—H

N hydrogen bonds. The dihedral angles between the planes of the thiazole and triazole rings and between the substituted phenyl and thiazole rings are 36.3 (2) and 47.1 (3)°, respectively.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680403079X/is6016sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680403079X/is6016Isup2.hkl Contains datablock I

CCDC reference: 259866

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.026
wR factor = 0.062
Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N5     -   H5B    ...          ?

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               2321
           Count of symmetry unique reflns         1358
           Completeness (_total/calc)            170.91%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       963
           Fraction of Friedel pairs measured     0.709
           Are heavy atom types Z>Si present          yes

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

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

2-Amino-4-(2,5-dichlorophenyl)-5-(1H-1,2,4-triazol-1-yl)-1,3-thiazole top

Crystal data top

C₁₁H₇Cl₂N₅S	F(000) = 632
M_r = 312.18	D_x = 1.574 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 847 reflections
a = 7.842 (2) Å	θ = 2.8–26.4°
b = 11.324 (3) Å	µ = 0.64 mm⁻¹
c = 14.840 (4) Å	T = 293 K
V = 1317.8 (6) Å³	Cubic, colourless
Z = 4	0.26 × 0.24 × 0.22 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2321 independent reflections
Radiation source: fine-focus sealed tube	2065 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
φ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
T_min = 0.842, T_max = 0.868	k = −13→13
6871 measured reflections	l = −17→11

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)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.063	w = 1/[σ²(F_o²) + (0.0284P)² + 0.1906P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2321 reflections	Δρ_max = 0.13 e Å⁻³
180 parameters	Δρ_min = −0.19 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 750 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.05 (7)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.18558 (8)	0.92926 (5)	0.21465 (4)	0.03984 (15)
Cl1	−0.02376 (8)	0.99790 (5)	−0.08471 (4)	0.05663 (19)
Cl2	0.23456 (9)	0.48866 (7)	−0.15771 (5)	0.0696 (2)
N1	0.2815 (2)	1.01777 (15)	0.05210 (12)	0.0401 (4)
N2	0.2546 (3)	1.13213 (17)	0.07811 (15)	0.0643 (7)
N3	0.4194 (3)	1.12287 (19)	−0.04678 (15)	0.0598 (6)
N4	0.0611 (2)	0.74991 (15)	0.12839 (11)	0.0363 (4)
N5	0.0245 (3)	0.74121 (19)	0.28473 (14)	0.0526 (5)
H5A	0.028 (3)	0.7831 (19)	0.3332 (11)	0.056 (8)*
H5B	−0.048 (3)	0.6845 (16)	0.2799 (18)	0.056 (8)*
C1	0.1164 (3)	0.7887 (2)	−0.03114 (14)	0.0346 (5)
C2	0.1704 (3)	0.67423 (19)	−0.05086 (15)	0.0371 (5)
H2	0.2111	0.6261	−0.0048	0.045*
C3	0.1642 (3)	0.6317 (2)	−0.13752 (16)	0.0462 (6)
C4	0.1081 (3)	0.7005 (3)	−0.20782 (17)	0.0538 (7)
H4	0.1076	0.6714	−0.2664	0.065*
C5	0.0528 (3)	0.8131 (2)	−0.18966 (15)	0.0512 (6)
H5	0.0132	0.8606	−0.2363	0.061*
C6	0.0557 (3)	0.8563 (2)	−0.10253 (14)	0.0400 (6)
C7	0.1253 (3)	0.82680 (18)	0.06407 (14)	0.0328 (5)
C8	0.1981 (3)	0.92585 (19)	0.09752 (13)	0.0356 (5)
C9	0.0799 (3)	0.79313 (19)	0.20912 (15)	0.0368 (5)
C10	0.3413 (5)	1.1899 (2)	0.01612 (19)	0.0761 (10)
H10	0.3483	1.2718	0.0157	0.091*
C11	0.3791 (3)	1.0151 (2)	−0.02241 (15)	0.0431 (6)
H11	0.4131	0.9468	−0.0523	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0529 (3)	0.0372 (3)	0.0294 (3)	−0.0030 (3)	0.0003 (3)	−0.0033 (2)
Cl1	0.0690 (4)	0.0489 (4)	0.0520 (4)	0.0118 (3)	−0.0051 (3)	0.0125 (3)
Cl2	0.0714 (4)	0.0604 (4)	0.0770 (5)	0.0032 (3)	−0.0037 (4)	−0.0356 (4)
N1	0.0557 (12)	0.0301 (9)	0.0347 (10)	−0.0044 (9)	0.0055 (9)	−0.0012 (8)
N2	0.107 (2)	0.0337 (11)	0.0520 (13)	−0.0100 (12)	0.0216 (14)	−0.0095 (10)
N3	0.0822 (17)	0.0494 (13)	0.0479 (12)	−0.0183 (12)	0.0107 (12)	0.0033 (10)
N4	0.0452 (11)	0.0334 (10)	0.0302 (10)	−0.0021 (8)	−0.0028 (9)	0.0007 (8)
N5	0.0788 (15)	0.0499 (13)	0.0292 (11)	−0.0172 (12)	0.0005 (12)	0.0044 (10)
C1	0.0324 (11)	0.0418 (13)	0.0296 (11)	−0.0040 (9)	0.0006 (10)	−0.0006 (10)
C2	0.0365 (12)	0.0381 (12)	0.0367 (12)	−0.0030 (10)	−0.0029 (10)	−0.0017 (10)
C3	0.0392 (13)	0.0499 (14)	0.0493 (15)	−0.0082 (11)	0.0029 (12)	−0.0190 (12)
C4	0.0583 (15)	0.0697 (19)	0.0333 (13)	−0.0141 (14)	−0.0017 (13)	−0.0122 (13)
C5	0.0547 (15)	0.0665 (18)	0.0324 (13)	−0.0081 (13)	−0.0067 (11)	0.0062 (12)
C6	0.0404 (13)	0.0441 (14)	0.0354 (13)	0.0002 (10)	−0.0009 (11)	0.0045 (10)
C7	0.0377 (12)	0.0317 (11)	0.0291 (11)	0.0018 (9)	−0.0007 (9)	0.0009 (9)
C8	0.0433 (12)	0.0358 (11)	0.0277 (10)	0.0016 (11)	0.0026 (10)	−0.0003 (9)
C9	0.0438 (12)	0.0363 (12)	0.0302 (12)	0.0021 (10)	−0.0023 (11)	0.0027 (10)
C10	0.133 (3)	0.0344 (15)	0.0608 (17)	−0.0204 (17)	0.024 (2)	−0.0030 (13)
C11	0.0521 (14)	0.0430 (14)	0.0343 (12)	−0.0037 (12)	0.0031 (11)	−0.0003 (11)

Geometric parameters (Å, º) top

S1—C8	1.741 (2)	N5—H5B	0.861 (10)
S1—C9	1.752 (2)	C1—C6	1.391 (3)
Cl1—C6	1.741 (2)	C1—C2	1.395 (3)
Cl2—C3	1.737 (3)	C1—C7	1.479 (3)
N1—C11	1.345 (3)	C2—C3	1.374 (3)
N1—N2	1.368 (2)	C2—H2	0.9300
N1—C8	1.402 (3)	C3—C4	1.374 (4)
N2—C10	1.318 (3)	C4—C5	1.373 (4)
N3—C11	1.312 (3)	C4—H4	0.9300
N3—C10	1.350 (4)	C5—C6	1.383 (3)
N4—C9	1.303 (3)	C5—H5	0.9300
N4—C7	1.386 (3)	C7—C8	1.353 (3)
N5—C9	1.339 (3)	C11—H11	0.9300
N5—H5A	0.862 (10)	C10—H10	0.9300

C8—S1—C9	87.73 (11)	C4—C5—C6	120.5 (2)
C11—N1—N2	109.97 (18)	C4—C5—H5	119.8
C11—N1—C8	130.07 (18)	C6—C5—H5	119.8
N2—N1—C8	119.68 (18)	C5—C6—C1	121.5 (2)
C10—N2—N1	101.1 (2)	C5—C6—Cl1	117.54 (18)
C11—N3—C10	102.9 (2)	C1—C6—Cl1	120.91 (17)
C9—N4—C7	110.87 (17)	C8—C7—N4	114.90 (18)
C9—N5—H5A	116.5 (17)	C8—C7—C1	127.8 (2)
C9—N5—H5B	118.2 (19)	N4—C7—C1	117.22 (19)
H5A—N5—H5B	120 (3)	C7—C8—N1	129.49 (18)
C6—C1—C2	117.1 (2)	C7—C8—S1	111.15 (16)
C6—C1—C7	125.7 (2)	N1—C8—S1	119.32 (15)
C2—C1—C7	117.21 (19)	N4—C9—N5	124.7 (2)
C3—C2—C1	120.7 (2)	N4—C9—S1	115.28 (16)
C3—C2—H2	119.6	N5—C9—S1	120.03 (18)
C1—C2—H2	119.6	N3—C11—N1	110.0 (2)
C2—C3—C4	121.6 (2)	N3—C11—H11	125.0
C2—C3—Cl2	118.5 (2)	N1—C11—H11	125.0
C4—C3—Cl2	119.94 (19)	N2—C10—N3	116.0 (2)
C5—C4—C3	118.6 (2)	N2—C10—H10	122.0
C5—C4—H4	120.7	N3—C10—H10	122.0
C3—C4—H4	120.7

C11—N1—N2—C10	−0.5 (3)	C2—C1—C7—N4	−47.1 (3)
C8—N1—N2—C10	−175.0 (2)	N4—C7—C8—N1	176.6 (2)
C6—C1—C2—C3	0.4 (3)	C1—C7—C8—N1	0.7 (4)
C7—C1—C2—C3	179.2 (2)	N4—C7—C8—S1	−1.3 (2)
C1—C2—C3—C4	1.3 (3)	C1—C7—C8—S1	−177.14 (18)
C1—C2—C3—Cl2	179.64 (17)	C11—N1—C8—C7	−34.0 (4)
C2—C3—C4—C5	−1.9 (4)	N2—N1—C8—C7	139.3 (3)
Cl2—C3—C4—C5	179.79 (19)	C11—N1—C8—S1	143.7 (2)
C3—C4—C5—C6	0.7 (4)	N2—N1—C8—S1	−43.0 (3)
C4—C5—C6—C1	1.0 (4)	C9—S1—C8—C7	−0.07 (18)
C4—C5—C6—Cl1	−177.76 (19)	C9—S1—C8—N1	−178.17 (18)
C2—C1—C6—C5	−1.6 (3)	C7—N4—C9—N5	177.3 (2)
C7—C1—C6—C5	179.8 (2)	C7—N4—C9—S1	−2.5 (2)
C2—C1—C6—Cl1	177.14 (16)	C8—S1—C9—N4	1.52 (18)
C7—C1—C6—Cl1	−1.5 (3)	C8—S1—C9—N5	−178.3 (2)
C9—N4—C7—C8	2.4 (3)	C10—N3—C11—N1	−0.2 (3)
C9—N4—C7—C1	178.75 (19)	N2—N1—C11—N3	0.5 (3)
C6—C1—C7—C8	−52.7 (3)	C8—N1—C11—N3	174.2 (2)
C2—C1—C7—C8	128.6 (3)	N1—N2—C10—N3	0.4 (4)
C6—C1—C7—N4	131.5 (2)	C11—N3—C10—N2	−0.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···N3ⁱ	0.86 (1)	2.12 (1)	2.969 (3)	170 (3)

Symmetry code: (i) −x+1/2, −y+2, z+1/2.

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2-Amino-4-(2,5-di­chloro­phenyl)-5-(1H-1,2,4-triazol-1-yl)-1,3-thia­zole

Supporting information

Key indicators

checkCIF/PLATON results

2-Amino-4-(2,5-dichlorophenyl)-5-(1H-1,2,4-triazol-1-yl)-1,3-thiazole