Ethyl 7-chloro-methyl-5-(2-chloro-phen-yl)-7-hydr-oxy-2-methyl-sulfanyl-4,5,6,7-tetra-hydro-1,2,4-triazolo[1,5-a]pyrimidine-6-carboxyl-ate.

In the title compound, C(16)H(18)Cl(2)N(4)O(3)S, the five-membered ring is almost planar [maximum deviation = 0.011 (3) Å] and the six-membered ring adopts an envelope conformation. In the crystal structure, N-H⋯N, O-H⋯N and C-H⋯O inter-actions link mol-ecules into a three-dimensional network.

Related literature

For general background to tetra­hydro triazolo[1,5-a]pyrimi­dine derivatives as potential biologically active compounds, see: Pryadeina et al. (2004 ▶). For related structures, see: Chen et al. (2005 ▶); Hu et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H18Cl2N4O3S

M = 417.30

Triclinic,

a = 8.4534 (14) Å

b = 10.5082 (17) Å

c = 12.0846 (19) Å

α = 66.660 (3)°

β = 79.519 (3)°

γ = 84.795 (3)°

V = 969.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.47 mm−1

T = 292 K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART 4K CCD diffractometer

Absorption correction: none

6772 measured reflections

3759 independent reflections

2661 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.141

S = 1.08

3759 reflections

249 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809039373/hb5113sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039373/hb5113Isup2.hkl

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

C16H18Cl2N4O3S	Z = 2
Mr = 417.30	F(000) = 432
Triclinic, P1	Dx = 1.430 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4534 (14) Å	Cell parameters from 2018 reflections
b = 10.5082 (17) Å	θ = 2.5–24.1°
c = 12.0846 (19) Å	µ = 0.47 mm−1
α = 66.660 (3)°	T = 292 K
β = 79.519 (3)°	Block, colourless
γ = 84.795 (3)°	0.30 × 0.20 × 0.10 mm
V = 969.0 (3) Å3

Bruker SMART 4K CCD diffractometer	2661 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
graphite	θmax = 26.0°, θmin = 1.9°
φ and ω scans	h = −10→10
6772 measured reflections	k = −12→12
3759 independent reflections	l = −14→14

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.07P)2] where P = (Fo2 + 2Fc2)/3
3759 reflections	(Δ/σ)max = 0.001
249 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1	0.68839 (13)	0.60065 (10)	0.98954 (7)	0.0933 (4)
Cl2	0.60921 (11)	0.36582 (8)	0.66235 (7)	0.0709 (3)
S1	1.08176 (11)	0.90864 (8)	0.17205 (6)	0.0681 (3)
C1	0.6041 (4)	0.7582 (3)	0.9073 (2)	0.0571 (8)
C2	0.4887 (4)	0.8210 (4)	0.9701 (3)	0.0747 (10)
H2	0.4601	0.7782	1.0543	0.090*
C3	0.4181 (4)	0.9457 (4)	0.9068 (3)	0.0775 (11)
H3	0.3413	0.9870	0.9483	0.093*
C4	0.4602 (4)	1.0087 (3)	0.7840 (3)	0.0684 (9)
H4	0.4126	1.0933	0.7415	0.082*
C5	0.5738 (3)	0.9472 (3)	0.7221 (2)	0.0510 (7)
H5	0.6018	0.9919	0.6380	0.061*
C6	0.6471 (3)	0.8217 (3)	0.7812 (2)	0.0414 (6)
C7	0.7640 (3)	0.7517 (2)	0.7107 (2)	0.0382 (6)
H7	0.835 (3)	0.694 (3)	0.758 (2)	0.046*
C8	0.6777 (3)	0.6492 (2)	0.6789 (2)	0.0351 (5)
H8	0.645 (3)	0.574 (2)	0.755 (2)	0.042*
C9	0.5292 (3)	0.7157 (3)	0.6256 (2)	0.0441 (6)
C10	0.2503 (4)	0.7571 (4)	0.6852 (3)	0.0809 (11)
H10A	0.1955	0.7190	0.6417	0.097*
H10B	0.2709	0.8541	0.6349	0.097*
C11	0.1517 (4)	0.7428 (4)	0.8024 (3)	0.0821 (11)
H11A	0.1188	0.6484	0.8461	0.123*
H11B	0.0582	0.8025	0.7881	0.123*
H11C	0.2133	0.7680	0.8496	0.123*
C12	0.7963 (3)	0.5897 (2)	0.5979 (2)	0.0369 (6)
C13	0.7175 (3)	0.5062 (3)	0.5449 (2)	0.0461 (6)
H13A	0.7998	0.4709	0.4964	0.055*
H13B	0.6449	0.5662	0.4916	0.055*
C14	0.8996 (3)	0.8292 (2)	0.5003 (2)	0.0395 (6)
C15	0.9936 (3)	0.8369 (3)	0.3248 (2)	0.0441 (6)
C16	1.0255 (5)	0.7895 (3)	0.1151 (3)	0.0830 (11)
H16A	1.0832	0.7033	0.1477	0.125*
H16B	1.0510	0.8271	0.0276	0.125*
H16C	0.9119	0.7740	0.1392	0.125*
N1	0.8465 (3)	0.8568 (2)	0.59986 (19)	0.0461 (6)
H1	0.894 (3)	0.929 (3)	0.608 (2)	0.055*
N2	0.8708 (3)	0.7083 (2)	0.49519 (17)	0.0410 (5)
N3	0.9342 (3)	0.7110 (2)	0.37947 (17)	0.0417 (5)
N4	0.9794 (3)	0.9135 (2)	0.39433 (17)	0.0441 (5)
O1	0.5267 (3)	0.7939 (2)	0.52207 (17)	0.0682 (6)
O2	0.4005 (2)	0.6814 (2)	0.71234 (18)	0.0611 (6)
O3	0.9120 (2)	0.51348 (18)	0.66938 (16)	0.0448 (5)
H3A	0.953 (4)	0.458 (3)	0.647 (3)	0.067*

	U11	U22	U33	U12	U13	U23
Cl1	0.1212 (8)	0.0852 (7)	0.0451 (5)	−0.0024 (6)	−0.0173 (5)	0.0064 (4)
Cl2	0.0932 (6)	0.0500 (5)	0.0662 (5)	−0.0327 (4)	−0.0159 (4)	−0.0111 (4)
S1	0.1055 (7)	0.0475 (5)	0.0361 (4)	−0.0024 (4)	0.0124 (4)	−0.0101 (3)
C1	0.073 (2)	0.0615 (19)	0.0356 (14)	−0.0172 (16)	0.0008 (14)	−0.0183 (13)
C2	0.084 (2)	0.101 (3)	0.0403 (16)	−0.028 (2)	0.0177 (16)	−0.0353 (18)
C3	0.078 (2)	0.087 (3)	0.081 (2)	−0.019 (2)	0.020 (2)	−0.056 (2)
C4	0.068 (2)	0.0568 (19)	0.084 (2)	−0.0057 (16)	0.0090 (18)	−0.0391 (17)
C5	0.0643 (18)	0.0407 (16)	0.0465 (15)	−0.0049 (14)	0.0028 (13)	−0.0194 (12)
C6	0.0477 (15)	0.0436 (15)	0.0343 (13)	−0.0110 (12)	0.0024 (11)	−0.0184 (11)
C7	0.0433 (15)	0.0344 (13)	0.0332 (12)	−0.0019 (11)	−0.0027 (11)	−0.0104 (10)
C8	0.0390 (14)	0.0291 (12)	0.0315 (12)	−0.0017 (10)	−0.0041 (10)	−0.0063 (10)
C9	0.0513 (16)	0.0398 (15)	0.0434 (15)	0.0048 (12)	−0.0119 (13)	−0.0179 (12)
C10	0.052 (2)	0.107 (3)	0.089 (3)	0.030 (2)	−0.0287 (18)	−0.043 (2)
C11	0.051 (2)	0.096 (3)	0.109 (3)	0.0175 (19)	−0.021 (2)	−0.051 (2)
C12	0.0450 (14)	0.0256 (12)	0.0385 (13)	−0.0016 (10)	−0.0073 (11)	−0.0102 (10)
C13	0.0582 (17)	0.0355 (14)	0.0434 (14)	−0.0058 (12)	−0.0109 (12)	−0.0117 (11)
C14	0.0477 (15)	0.0316 (13)	0.0369 (13)	−0.0033 (11)	0.0007 (11)	−0.0136 (10)
C15	0.0556 (16)	0.0331 (14)	0.0355 (13)	0.0054 (12)	0.0031 (11)	−0.0107 (11)
C16	0.141 (3)	0.067 (2)	0.0378 (16)	0.008 (2)	−0.0113 (18)	−0.0201 (15)
N1	0.0583 (14)	0.0386 (12)	0.0421 (12)	−0.0177 (11)	0.0107 (10)	−0.0208 (10)
N2	0.0537 (13)	0.0327 (11)	0.0351 (11)	−0.0054 (10)	0.0035 (9)	−0.0150 (8)
N3	0.0580 (14)	0.0316 (11)	0.0339 (11)	0.0016 (10)	−0.0019 (9)	−0.0138 (9)
N4	0.0567 (14)	0.0328 (11)	0.0374 (11)	−0.0029 (10)	0.0074 (10)	−0.0137 (9)
O1	0.0783 (15)	0.0711 (14)	0.0463 (12)	0.0242 (12)	−0.0219 (10)	−0.0138 (10)
O2	0.0390 (11)	0.0711 (14)	0.0615 (12)	0.0076 (10)	−0.0113 (9)	−0.0140 (10)
O3	0.0513 (11)	0.0359 (10)	0.0513 (11)	0.0109 (8)	−0.0149 (9)	−0.0207 (8)

Cl1—C1	1.725 (3)	C10—O2	1.454 (3)
Cl2—C13	1.773 (2)	C10—C11	1.465 (5)
S1—C15	1.740 (2)	C10—H10A	0.9700
S1—C16	1.783 (4)	C10—H10B	0.9700
C1—C6	1.392 (3)	C11—H11A	0.9600
C1—C2	1.404 (4)	C11—H11B	0.9600
C2—C3	1.374 (5)	C11—H11C	0.9600
C2—H2	0.9300	C12—O3	1.401 (3)
C3—C4	1.356 (4)	C12—N2	1.456 (3)
C3—H3	0.9300	C12—C13	1.526 (3)
C4—C5	1.381 (4)	C13—H13A	0.9700
C4—H4	0.9300	C13—H13B	0.9700
C5—C6	1.378 (4)	C14—N4	1.332 (3)
C5—H5	0.9300	C14—N1	1.337 (3)
C6—C7	1.517 (4)	C14—N2	1.342 (3)
C7—N1	1.458 (3)	C15—N3	1.321 (3)
C7—C8	1.554 (3)	C15—N4	1.360 (3)
C7—H7	0.92 (3)	C16—H16A	0.9600
C8—C9	1.502 (3)	C16—H16B	0.9600
C8—C12	1.539 (3)	C16—H16C	0.9600
C8—H8	0.96 (2)	N1—H1	0.93 (3)
C9—O1	1.198 (3)	N2—N3	1.393 (3)
C9—O2	1.329 (3)	O3—H3A	0.77 (3)
C15—S1—C16	101.76 (14)	C10—C11—H11A	109.5
C6—C1—C2	120.3 (3)	C10—C11—H11B	109.5
C6—C1—Cl1	121.1 (2)	H11A—C11—H11B	109.5
C2—C1—Cl1	118.6 (2)	C10—C11—H11C	109.5
C3—C2—C1	119.9 (3)	H11A—C11—H11C	109.5
C3—C2—H2	120.0	H11B—C11—H11C	109.5
C1—C2—H2	120.0	O3—C12—N2	109.8 (2)
C4—C3—C2	120.2 (3)	O3—C12—C13	113.3 (2)
C4—C3—H3	119.9	N2—C12—C13	107.02 (19)
C2—C3—H3	119.9	O3—C12—C8	105.82 (18)
C3—C4—C5	120.0 (3)	N2—C12—C8	106.35 (18)
C3—C4—H4	120.0	C13—C12—C8	114.3 (2)
C5—C4—H4	120.0	C12—C13—Cl2	111.07 (17)
C6—C5—C4	122.1 (3)	C12—C13—H13A	109.4
C6—C5—H5	119.0	Cl2—C13—H13A	109.4
C4—C5—H5	119.0	C12—C13—H13B	109.4
C5—C6—C1	117.5 (2)	Cl2—C13—H13B	109.4
C5—C6—C7	121.2 (2)	H13A—C13—H13B	108.0
C1—C6—C7	121.2 (2)	N4—C14—N1	127.2 (2)
N1—C7—C6	109.5 (2)	N4—C14—N2	110.8 (2)
N1—C7—C8	110.5 (2)	N1—C14—N2	121.9 (2)
C6—C7—C8	111.7 (2)	N3—C15—N4	116.1 (2)
N1—C7—H7	112.1 (16)	N3—C15—S1	124.2 (2)
C6—C7—H7	111.0 (16)	N4—C15—S1	119.66 (19)
C8—C7—H7	101.9 (16)	S1—C16—H16A	109.5
C9—C8—C12	113.9 (2)	S1—C16—H16B	109.5
C9—C8—C7	110.8 (2)	H16A—C16—H16B	109.5
C12—C8—C7	110.40 (19)	S1—C16—H16C	109.5
C9—C8—H8	108.1 (15)	H16A—C16—H16C	109.5
C12—C8—H8	107.5 (14)	H16B—C16—H16C	109.5
C7—C8—H8	105.7 (14)	C14—N1—C7	120.7 (2)
O1—C9—O2	124.5 (3)	C14—N1—H1	118.2 (17)
O1—C9—C8	125.5 (3)	C7—N1—H1	117.4 (16)
O2—C9—C8	109.9 (2)	C14—N2—N3	109.23 (18)
O2—C10—C11	107.0 (3)	C14—N2—C12	124.9 (2)
O2—C10—H10A	110.3	N3—N2—C12	125.74 (19)
C11—C10—H10A	110.3	C15—N3—N2	101.43 (19)
O2—C10—H10B	110.3	C14—N4—C15	102.3 (2)
C11—C10—H10B	110.3	C9—O2—C10	118.2 (2)
H10A—C10—H10B	108.6	C12—O3—H3A	111 (2)
C6—C1—C2—C3	−0.1 (5)	N2—C12—C13—Cl2	−175.47 (17)
Cl1—C1—C2—C3	−179.3 (3)	C8—C12—C13—Cl2	−58.0 (2)
C1—C2—C3—C4	−0.4 (5)	C16—S1—C15—N3	12.5 (3)
C2—C3—C4—C5	0.3 (5)	C16—S1—C15—N4	−165.8 (2)
C3—C4—C5—C6	0.3 (5)	N4—C14—N1—C7	−178.5 (2)
C4—C5—C6—C1	−0.7 (4)	N2—C14—N1—C7	4.3 (4)
C4—C5—C6—C7	176.2 (3)	C6—C7—N1—C14	−151.3 (2)
C2—C1—C6—C5	0.6 (4)	C8—C7—N1—C14	−27.9 (3)
Cl1—C1—C6—C5	179.8 (2)	N4—C14—N2—N3	−0.1 (3)
C2—C1—C6—C7	−176.3 (3)	N1—C14—N2—N3	177.5 (2)
Cl1—C1—C6—C7	2.8 (4)	N4—C14—N2—C12	175.4 (2)
C5—C6—C7—N1	30.3 (3)	N1—C14—N2—C12	−7.0 (4)
C1—C6—C7—N1	−152.8 (2)	O3—C12—N2—C14	−82.2 (3)
C5—C6—C7—C8	−92.4 (3)	C13—C12—N2—C14	154.4 (2)
C1—C6—C7—C8	84.5 (3)	C8—C12—N2—C14	31.9 (3)
N1—C7—C8—C9	−74.3 (3)	O3—C12—N2—N3	92.6 (3)
C6—C7—C8—C9	47.9 (3)	C13—C12—N2—N3	−30.8 (3)
N1—C7—C8—C12	52.8 (3)	C8—C12—N2—N3	−153.3 (2)
C6—C7—C8—C12	175.02 (19)	N4—C15—N3—N2	1.9 (3)
C12—C8—C9—O1	−45.3 (3)	S1—C15—N3—N2	−176.39 (19)
C7—C8—C9—O1	79.9 (3)	C14—N2—N3—C15	−1.1 (3)
C12—C8—C9—O2	138.4 (2)	C12—N2—N3—C15	−176.5 (2)
C7—C8—C9—O2	−96.4 (2)	N1—C14—N4—C15	−176.3 (3)
C9—C8—C12—O3	−170.66 (19)	N2—C14—N4—C15	1.2 (3)
C7—C8—C12—O3	64.0 (2)	N3—C15—N4—C14	−2.0 (3)
C9—C8—C12—N2	72.6 (2)	S1—C15—N4—C14	176.38 (19)
C7—C8—C12—N2	−52.8 (2)	O1—C9—O2—C10	−8.7 (4)
C9—C8—C12—C13	−45.3 (3)	C8—C9—O2—C10	167.6 (3)
C7—C8—C12—C13	−170.64 (19)	C11—C10—O2—C9	−157.3 (3)
O3—C12—C13—Cl2	63.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4i	0.93 (3)	2.04 (3)	2.969 (3)	172 (2)
O3—H3A···N3ii	0.77 (3)	2.05 (3)	2.806 (3)	170 (3)
C16—H16A···O3ii	0.96	2.47	3.290 (4)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N4i	0.93 (3)	2.04 (3)	2.969 (3)	172 (2)
O3—H3A⋯N3ii	0.77 (3)	2.05 (3)	2.806 (3)	170 (3)
C16—H16A⋯O3ii	0.96	2.47	3.290 (4)	143

Symmetry codes: (i) ; (ii) .