3-[6-(2,4-Dichloro­phen­yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazin-3-yl]propan-1-ol

In the title compound, C₁₃H₁₂Cl₂N₄OS, the triazole and benzene rings are planar, while the six-membered thia­diazine ring has a screw-boat conformation. Inter­molecular O—H...N hydrogen bonds form chains which enhance the stability of the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.048
• wR factor = 0.142
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.01

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

   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C13H12Cl2N4OS	Z = 2
Mr = 343.23	F(000) = 352
Triclinic, P1	Dx = 1.553 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1605 (7) Å	Cell parameters from 2358 reflections
b = 8.5239 (8) Å	θ = 2.6–25.0°
c = 11.2810 (9) Å	µ = 0.59 mm^−1
α = 95.237 (2)°	T = 298 K
β = 105.340 (2)°	Block, colorless
γ = 101.205 (2)°	0.38 × 0.26 × 0.20 mm
V = 733.82 (11) Å^3

Data collection

Bruker APEX area-detector diffractometer	2564 independent reflections
Radiation source: fine-focus sealed tube	2317 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
φ and ω scan	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −7→9
Tmin = 0.808, Tmax = 0.892	k = −10→9
3875 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0816P)^2 + 0.4287P] where P = (Fo^2 + 2Fc^2)/3
2564 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 1.13 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	1.36864 (11)	0.58844 (10)	1.08560 (8)	0.0667 (3)
Cl2	1.22775 (10)	1.13873 (8)	0.93595 (7)	0.0604 (3)
S1	0.84880 (10)	1.21134 (8)	0.68068 (8)	0.0549 (3)
O1	0.2369 (4)	0.3151 (3)	0.5161 (3)	0.1020 (10)
H1	0.3115	0.2659	0.5451	0.153*
N1	0.7360 (3)	0.8717 (3)	0.7568 (2)	0.0433 (5)
N2	0.6143 (3)	0.9463 (2)	0.6890 (2)	0.0421 (5)
N3	0.4903 (3)	1.1397 (3)	0.6211 (2)	0.0544 (6)
N4	0.3608 (3)	1.0081 (3)	0.6281 (2)	0.0538 (6)
C1	1.2368 (4)	0.6866 (4)	0.9854 (3)	0.0485 (6)
C2	1.2805 (3)	0.8524 (3)	0.9959 (2)	0.0478 (6)
H2	1.3810	0.9120	1.0553	0.057*
C3	1.1731 (3)	0.9292 (3)	0.9171 (2)	0.0446 (6)
C4	1.0202 (3)	0.8426 (3)	0.8284 (2)	0.0427 (6)
C5	0.9823 (4)	0.6740 (3)	0.8212 (3)	0.0476 (6)
H5	0.8814	0.6132	0.7629	0.057*
C6	1.0887 (4)	0.5964 (3)	0.8969 (3)	0.0516 (7)
H6	1.0621	0.4840	0.8890	0.062*
C7	0.8924 (3)	0.9198 (3)	0.7504 (2)	0.0424 (6)
C8	0.9399 (4)	1.0348 (3)	0.6652 (3)	0.0471 (6)
H8A	0.8955	0.9805	0.5799	0.056*
H8B	1.0658	1.0685	0.6853	0.056*
C9	0.6387 (4)	1.0994 (3)	0.6583 (2)	0.0459 (6)
C10	0.4372 (3)	0.8962 (3)	0.6692 (3)	0.0457 (6)
C11	0.3517 (4)	0.7336 (4)	0.6885 (3)	0.0564 (7)
H11A	0.2296	0.7307	0.6794	0.068*
H11B	0.4047	0.7181	0.7730	0.068*
C12	0.3641 (4)	0.5943 (3)	0.5997 (3)	0.0543 (7)
H12A	0.3356	0.6201	0.5157	0.065*
H12B	0.4829	0.5799	0.6215	0.065*
C13	0.2420 (4)	0.4394 (4)	0.6040 (4)	0.0723 (10)
H13A	0.2786	0.4083	0.6858	0.087*
H13B	0.1255	0.4580	0.5915	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0600 (5)	0.0688 (5)	0.0729 (5)	0.0214 (4)	0.0146 (4)	0.0182 (4)
Cl2	0.0626 (5)	0.0417 (4)	0.0633 (5)	−0.0004 (3)	0.0076 (4)	−0.0020 (3)
S1	0.0479 (4)	0.0378 (4)	0.0694 (5)	−0.0035 (3)	0.0120 (3)	0.0036 (3)
O1	0.100 (2)	0.0616 (17)	0.120 (2)	0.0161 (15)	−0.0007 (18)	−0.0077 (16)
N1	0.0421 (12)	0.0427 (12)	0.0440 (11)	0.0049 (9)	0.0152 (9)	0.0032 (9)
N2	0.0384 (11)	0.0382 (11)	0.0474 (12)	0.0017 (9)	0.0158 (9)	0.0003 (9)
N3	0.0502 (14)	0.0424 (13)	0.0665 (15)	0.0083 (10)	0.0147 (12)	−0.0014 (11)
N4	0.0435 (13)	0.0510 (14)	0.0651 (15)	0.0078 (11)	0.0189 (11)	−0.0040 (11)
C1	0.0458 (15)	0.0547 (16)	0.0484 (15)	0.0115 (12)	0.0196 (12)	0.0068 (12)
C2	0.0416 (14)	0.0510 (16)	0.0469 (15)	0.0043 (12)	0.0138 (12)	−0.0010 (12)
C3	0.0428 (14)	0.0419 (14)	0.0479 (14)	0.0030 (11)	0.0181 (12)	−0.0006 (11)
C4	0.0390 (13)	0.0452 (14)	0.0439 (13)	0.0036 (11)	0.0181 (11)	0.0022 (11)
C5	0.0421 (14)	0.0447 (15)	0.0498 (15)	−0.0014 (11)	0.0128 (12)	0.0012 (12)
C6	0.0553 (17)	0.0427 (15)	0.0561 (16)	0.0027 (12)	0.0216 (13)	0.0048 (12)
C7	0.0425 (14)	0.0380 (13)	0.0435 (13)	0.0017 (10)	0.0150 (11)	−0.0005 (10)
C8	0.0428 (14)	0.0463 (15)	0.0504 (15)	0.0010 (11)	0.0179 (12)	0.0051 (12)
C9	0.0457 (15)	0.0386 (14)	0.0487 (14)	0.0025 (11)	0.0136 (12)	−0.0024 (11)
C10	0.0406 (14)	0.0455 (15)	0.0514 (15)	0.0051 (11)	0.0206 (11)	−0.0034 (12)
C11	0.0470 (16)	0.0525 (17)	0.0739 (19)	0.0018 (13)	0.0321 (15)	0.0067 (14)
C12	0.0523 (16)	0.0437 (16)	0.0679 (18)	0.0059 (13)	0.0232 (14)	0.0064 (13)
C13	0.0501 (18)	0.0483 (18)	0.112 (3)	0.0059 (14)	0.0180 (18)	0.0059 (18)

Geometric parameters (Å, º)

Cl1—C1	1.736 (3)	C4—C5	1.400 (4)
Cl2—C3	1.733 (3)	C4—C7	1.477 (4)
S1—C9	1.733 (3)	C5—C6	1.362 (4)
S1—C8	1.817 (3)	C5—H5	0.930
O1—C13	1.370 (5)	C6—H6	0.930
O1—H1	0.820	C7—C8	1.502 (4)
N1—C7	1.286 (3)	C8—H8A	0.970
N1—N2	1.381 (3)	C8—H8B	0.970
N2—C9	1.371 (3)	C10—C11	1.488 (4)
N2—C10	1.376 (3)	C11—C12	1.519 (4)
N3—C9	1.296 (4)	C11—H11A	0.970
N3—N4	1.408 (3)	C11—H11B	0.970
N4—C10	1.293 (4)	C12—C13	1.505 (4)
C1—C2	1.375 (4)	C12—H12A	0.970
C1—C6	1.382 (4)	C12—H12B	0.970
C2—C3	1.380 (4)	C13—H13A	0.970
C2—H2	0.930	C13—H13B	0.970
C3—C4	1.396 (4)
C9—S1—C8	94.31 (13)	C7—C8—H8A	109.5
C13—O1—H1	109.5	S1—C8—H8A	109.5
C7—N1—N2	115.3 (2)	C7—C8—H8B	109.5
C9—N2—C10	105.1 (2)	S1—C8—H8B	109.5
C9—N2—N1	128.7 (2)	H8A—C8—H8B	108.1
C10—N2—N1	124.0 (2)	N3—C9—N2	110.4 (2)
C9—N3—N4	106.9 (2)	N3—C9—S1	130.0 (2)
C10—N4—N3	107.8 (2)	N2—C9—S1	119.5 (2)
C2—C1—C6	121.1 (3)	N4—C10—N2	109.8 (2)
C2—C1—Cl1	119.6 (2)	N4—C10—C11	126.8 (3)
C6—C1—Cl1	119.3 (2)	N2—C10—C11	123.4 (3)
C1—C2—C3	119.1 (3)	C10—C11—C12	114.3 (2)
C1—C2—H2	120.5	C10—C11—H11A	108.7
C3—C2—H2	120.5	C12—C11—H11A	108.7
C2—C3—C4	121.5 (3)	C10—C11—H11B	108.7
C2—C3—Cl2	118.0 (2)	C12—C11—H11B	108.7
C4—C3—Cl2	120.4 (2)	H11A—C11—H11B	107.6
C3—C4—C5	117.1 (3)	C13—C12—C11	111.4 (3)
C3—C4—C7	123.5 (2)	C13—C12—H12A	109.4
C5—C4—C7	119.2 (2)	C11—C12—H12A	109.4
C6—C5—C4	122.1 (3)	C13—C12—H12B	109.4
C6—C5—H5	119.0	C11—C12—H12B	109.4
C4—C5—H5	119.0	H12A—C12—H12B	108.0
C5—C6—C1	119.1 (3)	O1—C13—C12	112.8 (3)
C5—C6—H6	120.4	O1—C13—H13A	109.0
C1—C6—H6	120.4	C12—C13—H13A	109.0
N1—C7—C4	113.7 (2)	O1—C13—H13B	109.0
N1—C7—C8	123.5 (2)	C12—C13—H13B	109.0
C4—C7—C8	122.7 (2)	H13A—C13—H13B	107.8
C7—C8—S1	110.51 (18)
C7—N1—N2—C9	−29.0 (4)	N1—C7—C8—S1	49.7 (3)
C7—N1—N2—C10	170.3 (2)	C4—C7—C8—S1	−134.7 (2)
C9—N3—N4—C10	0.2 (3)	C9—S1—C8—C7	−52.0 (2)
C6—C1—C2—C3	0.6 (4)	N4—N3—C9—N2	0.4 (3)
Cl1—C1—C2—C3	−178.91 (19)	N4—N3—C9—S1	−175.6 (2)
C1—C2—C3—C4	0.9 (4)	C10—N2—C9—N3	−0.9 (3)
C1—C2—C3—Cl2	177.9 (2)	N1—N2—C9—N3	−164.5 (2)
C2—C3—C4—C5	−1.2 (4)	C10—N2—C9—S1	175.65 (19)
Cl2—C3—C4—C5	−178.18 (19)	N1—N2—C9—S1	12.1 (4)
C2—C3—C4—C7	173.8 (2)	C8—S1—C9—N3	−157.3 (3)
Cl2—C3—C4—C7	−3.1 (4)	C8—S1—C9—N2	27.0 (2)
C3—C4—C5—C6	0.0 (4)	N3—N4—C10—N2	−0.7 (3)
C7—C4—C5—C6	−175.2 (2)	N3—N4—C10—C11	−178.3 (3)
C4—C5—C6—C1	1.4 (4)	C9—N2—C10—N4	1.0 (3)
C2—C1—C6—C5	−1.8 (4)	N1—N2—C10—N4	165.6 (2)
Cl1—C1—C6—C5	177.8 (2)	C9—N2—C10—C11	178.6 (3)
N2—N1—C7—C4	177.4 (2)	N1—N2—C10—C11	−16.8 (4)
N2—N1—C7—C8	−6.7 (3)	N4—C10—C11—C12	111.5 (3)
C3—C4—C7—N1	−125.5 (3)	N2—C10—C11—C12	−65.7 (4)
C5—C4—C7—N1	49.5 (3)	C10—C11—C12—C13	−166.9 (3)
C3—C4—C7—C8	58.6 (4)	C11—C12—C13—O1	173.8 (3)
C5—C4—C7—C8	−126.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3^i	0.82	2.03	2.854 (4)	178

Symmetry code: (i) x, y−1, z.