Ethyl 5-chloro­methyl-2-methyl­sulfanyl-7-phenyl-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine-6-carboxyl­ate

Song, D.-D.; Chen, Q.

doi:10.1107/S1600536807062629

organic compounds

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Volume 64| Part 1| January 2008| Page o45

https://doi.org/10.1107/S1600536807062629

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Ethyl 5-chloromethyl-2-methylsulfanyl-7-phenyl-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine-6-carboxylate

Dan-Dan Song ^a and Qiong Chen ^b ^*

^aCollege of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China, and ^bKey Laboratory of Pesticides and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: qchen@mail.ccnu.edu.cn

(Received 23 November 2007; accepted 23 November 2007; online 6 December 2007)

In the title compound, C₁₆H₁₇ClN₄O₂S, the bicyclic triazolopyrimidine ring system is nearly planar and oriented with respect to the benzene ring at a dihedral angle of 87.24 (3)°. In the crystal structure, intermolecular N—H⋯N hydrogen bonds link the molecules into centrosymmetric dimers; an intramolecular C—H⋯O hydrogen bond is also present.

Related literature

For related literature, see: Fedorova et al. (2003 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₇ClN₄O₂S
M_r = 364.85
Triclinic, $[P \overline 1]$
a = 8.9280 (8) Å
b = 9.8217 (9) Å
c = 11.3775 (10) Å
α = 106.022 (2)°
β = 102.631 (2)°
γ = 109.919 (2)°
V = 845.85 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 292 (2) K
0.20 × 0.10 × 0.02 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: none
6662 measured reflections
3281 independent reflections
2295 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.156
S = 1.02
3281 reflections
222 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯N2ⁱ	0.85 (3)	2.11 (3)	2.939 (3)	164 (3)
C7—H7B⋯O2	0.97	2.15	2.888 (4)	132
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807062629/hk2399sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062629/hk2399Isup2.hkl

checkCIF report

Comment top

In recent years, growing attention has been paid to analogues of purines and nucleosides, including azolopyrimidines containing the bridge head nitrogen atom and their dihydro derivatives, among which promising biologically active compounds were found (Fedorova et al., 2003). We synthesized a novel class of ethyl 7-alkylthio-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine-6-carboxylate derivatives by three component condensation of 3-amino-5-alkylthio-1,2,4 -triazoles with aromatic aldehydes and β-keto ester. We report herein the crystal structure of one such analogue, a triazolopyrimidine derivative, the title compound, (I).

In the molecule of (I), (Fig. 1) the bond lengths and angles are within normal ranges (Allen et al., 1987). Rings A (N1—N3/C2/C3), B (N3/N4/C3—C6) and C (C11—C16) are, of course, planar. The bicyclic triazolopyrimidine ring system (N1—N4/C2—C6) is nearly planar with a maximum deviation of 0.152 (3) Å (for atom C6), and it is oriented with respect to ring C at a dihedral angle of 87.24 (3)°.

In the crystal structure, intermolecular N—H···N hydrogen bonds (Table 1, Fig 2) link the molecules into centrosymmetric dimers; an intramolecular C—H···O hydrogen bond (Table 1) is also present.

Related literature top

For related literature, see: Fedorova et al. (2003). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, a mixture of 4-chloro acetylacetic ester (1 mmol), benzaldehyde (1 mmol), and 3-amino-5-methylthio-1,2,4-triazole (1 mmol) in EtOH (3 ml) was added into a microwave tube. The sealed tube was placed in a Smith synthesizer and irradiated at 333 K for 30 min. The reaction mixture was cooled to room temperature, and the precipitate was filtered and recrystallized from ethanol to give the title compound, (I). Single crystals of (I) suitable for X-ray analysis were grown from an acetone solution at 293 K. ¹H NMR (CDCl3, 400 MHz): σ 10.56(s, 1 H), 7.28–7.33(m, 5 H), 6.40(s, 1H), 5.14(d, 1H), 4.95(d, 1H), 4.11(q,2 H), 2.51(s, 3H),1.15(t, 3H).

Structure description top

For related literature, see: Fedorova et al. (2003). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

Ethyl 5-chloromethyl-2-methylsulfanyl-7-phenyl-4,7-dihydro- 1,2,4-triazolo[1,5-a]pyrimidine-6-carboxylate top

Crystal data top

C₁₆H₁₇ClN₄O₂S	Z = 2
M_r = 364.85	F(000) = 380
Triclinic, P1	D_x = 1.433 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9280 (8) Å	Cell parameters from 1660 reflections
b = 9.8217 (9) Å	θ = 2.4–22.5°
c = 11.3775 (10) Å	µ = 0.37 mm⁻¹
α = 106.022 (2)°	T = 292 K
β = 102.631 (2)°	Block, colorless
γ = 109.919 (2)°	0.20 × 0.10 × 0.02 mm
V = 845.85 (13) Å³

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2295 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.030
Graphite monochromator	θ_max = 26.0°, θ_min = 2.4°
φ and ω scans	h = −10→11
6662 measured reflections	k = −12→12
3281 independent reflections	l = −14→13

Refinement top

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0839P)²P] where P = (F_o² + 2F_c²)/3
3281 reflections	(Δ/σ)_max = 0.001
222 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₆H₁₇ClN₄O₂S	γ = 109.919 (2)°
M_r = 364.85	V = 845.85 (13) Å³
Triclinic, P1	Z = 2
a = 8.9280 (8) Å	Mo Kα radiation
b = 9.8217 (9) Å	µ = 0.37 mm⁻¹
c = 11.3775 (10) Å	T = 292 K
α = 106.022 (2)°	0.20 × 0.10 × 0.02 mm
β = 102.631 (2)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2295 reflections with I > 2σ(I)
6662 measured reflections	R_int = 0.030
3281 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.40 e Å⁻³
3281 reflections	Δρ_min = −0.42 e Å⁻³
222 parameters

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
Cl1	0.52275 (12)	0.20019 (13)	0.21023 (8)	0.0802 (4)
S1	0.33719 (10)	0.12878 (9)	0.82617 (8)	0.0506 (3)
O1	0.7924 (2)	0.7426 (2)	0.57614 (18)	0.0458 (5)
O2	0.8859 (3)	0.6249 (3)	0.4314 (2)	0.0745 (8)
N1	0.5299 (3)	0.3688 (3)	0.7737 (2)	0.0399 (6)
N2	0.4832 (3)	0.1259 (2)	0.6417 (2)	0.0394 (6)
N3	0.6027 (3)	0.3760 (2)	0.6786 (2)	0.0378 (5)
N4	0.6300 (3)	0.2107 (3)	0.5023 (2)	0.0423 (6)
H4	0.603 (4)	0.119 (4)	0.448 (3)	0.051*
C1	0.3128 (5)	0.2917 (4)	0.9220 (4)	0.0875 (14)
H1A	0.4175	0.3619	0.9926	0.131*
H1B	0.2245	0.2552	0.9564	0.131*
H1C	0.2831	0.3456	0.8687	0.131*
C2	0.4589 (3)	0.2173 (3)	0.7451 (3)	0.0372 (6)
C3	0.5739 (3)	0.2331 (3)	0.6044 (2)	0.0355 (6)
C4	0.6994 (3)	0.3357 (3)	0.4670 (3)	0.0396 (7)
C5	0.7350 (3)	0.4840 (3)	0.5433 (3)	0.0373 (6)
C6	0.7104 (3)	0.5239 (3)	0.6746 (3)	0.0371 (6)
H6	0.6505	0.5913	0.6795	0.045*
C7	0.7226 (4)	0.2871 (3)	0.3381 (3)	0.0480 (8)
H7A	0.7719	0.2125	0.3329	0.058*
H7B	0.7995	0.3778	0.3290	0.058*
C8	0.8112 (4)	0.6191 (3)	0.5077 (3)	0.0434 (7)
C9	0.8778 (4)	0.8879 (3)	0.5616 (3)	0.0488 (8)
H9A	0.8284	0.8785	0.4733	0.059*
H9B	0.9972	0.9124	0.5791	0.059*
C10	0.8580 (4)	1.0149 (4)	0.6559 (3)	0.0606 (9)
H10A	0.7394	0.9875	0.6405	0.091*
H10B	0.9090	1.1114	0.6446	0.091*
H10C	0.9127	1.0274	0.7433	0.091*
C11	0.8775 (3)	0.6081 (3)	0.7886 (3)	0.0361 (6)
C12	0.9729 (4)	0.5313 (4)	0.8217 (3)	0.0583 (9)
H12	0.9337	0.4245	0.7752	0.070*
C13	1.1272 (5)	0.6119 (5)	0.9238 (4)	0.0715 (11)
H13	1.1902	0.5587	0.9461	0.086*
C14	1.1866 (4)	0.7682 (5)	0.9914 (3)	0.0668 (10)
H14	1.2904	0.8218	1.0595	0.080*
C15	1.0946 (4)	0.8466 (4)	0.9596 (3)	0.0609 (9)
H15	1.1353	0.9536	1.0058	0.073*
C16	0.9403 (4)	0.7662 (3)	0.8584 (3)	0.0489 (8)
H16	0.8778	0.8202	0.8371	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0749 (7)	0.1054 (8)	0.0463 (5)	0.0385 (6)	0.0133 (5)	0.0154 (5)
S1	0.0548 (5)	0.0413 (4)	0.0518 (5)	0.0097 (3)	0.0306 (4)	0.0165 (4)
O1	0.0558 (13)	0.0343 (11)	0.0494 (12)	0.0146 (9)	0.0248 (10)	0.0193 (9)
O2	0.110 (2)	0.0528 (14)	0.0817 (18)	0.0305 (14)	0.0683 (17)	0.0341 (13)
N1	0.0438 (13)	0.0347 (12)	0.0378 (13)	0.0112 (10)	0.0208 (11)	0.0105 (10)
N2	0.0406 (13)	0.0330 (12)	0.0386 (13)	0.0095 (10)	0.0172 (10)	0.0107 (10)
N3	0.0428 (13)	0.0293 (11)	0.0386 (13)	0.0089 (10)	0.0217 (11)	0.0112 (10)
N4	0.0532 (15)	0.0280 (12)	0.0428 (14)	0.0125 (11)	0.0260 (12)	0.0084 (10)
C1	0.112 (3)	0.058 (2)	0.099 (3)	0.025 (2)	0.081 (3)	0.019 (2)
C2	0.0364 (15)	0.0345 (14)	0.0341 (14)	0.0096 (11)	0.0135 (12)	0.0096 (11)
C3	0.0370 (15)	0.0319 (14)	0.0339 (14)	0.0100 (11)	0.0155 (12)	0.0109 (11)
C4	0.0403 (16)	0.0363 (15)	0.0401 (15)	0.0121 (12)	0.0184 (13)	0.0133 (12)
C5	0.0394 (16)	0.0350 (14)	0.0375 (15)	0.0129 (12)	0.0182 (13)	0.0140 (12)
C6	0.0421 (16)	0.0276 (13)	0.0412 (15)	0.0113 (11)	0.0198 (13)	0.0127 (11)
C7	0.0542 (18)	0.0405 (16)	0.0429 (17)	0.0122 (14)	0.0226 (14)	0.0126 (13)
C8	0.0467 (17)	0.0381 (16)	0.0400 (16)	0.0109 (13)	0.0170 (14)	0.0147 (13)
C9	0.0513 (18)	0.0415 (16)	0.0533 (19)	0.0133 (14)	0.0162 (15)	0.0274 (15)
C10	0.064 (2)	0.0424 (17)	0.072 (2)	0.0197 (16)	0.0217 (18)	0.0227 (16)
C11	0.0405 (15)	0.0315 (14)	0.0370 (15)	0.0113 (12)	0.0202 (12)	0.0140 (11)
C12	0.062 (2)	0.0453 (18)	0.061 (2)	0.0243 (16)	0.0141 (17)	0.0144 (16)
C13	0.062 (2)	0.079 (3)	0.074 (3)	0.038 (2)	0.012 (2)	0.028 (2)
C14	0.050 (2)	0.075 (3)	0.053 (2)	0.0146 (19)	0.0068 (16)	0.0160 (19)
C15	0.067 (2)	0.0408 (17)	0.0473 (19)	0.0064 (16)	0.0113 (17)	0.0051 (15)
C16	0.0585 (19)	0.0382 (16)	0.0425 (17)	0.0175 (14)	0.0136 (15)	0.0118 (13)

Geometric parameters (Å, º) top

N1—N3	1.385 (3)	C7—H7B	0.9700
N4—H4	0.85 (3)	C8—O2	1.207 (3)
C1—S1	1.782 (4)	C8—O1	1.334 (3)
C1—H1A	0.9600	C9—O1	1.446 (3)
C1—H1B	0.9600	C9—C10	1.494 (4)
C1—H1C	0.9600	C9—H9A	0.9700
C2—N1	1.312 (3)	C9—H9B	0.9700
C2—N2	1.378 (3)	C10—H10A	0.9600
C2—S1	1.740 (3)	C10—H10B	0.9600
C3—N3	1.324 (3)	C10—H10C	0.9600
C3—N2	1.326 (3)	C11—C16	1.374 (4)
C3—N4	1.356 (3)	C11—C12	1.376 (4)
C4—C5	1.357 (4)	C12—C13	1.387 (4)
C4—N4	1.384 (3)	C12—H12	0.9300
C4—C7	1.495 (4)	C13—C14	1.358 (5)
C5—C8	1.480 (4)	C13—H13	0.9300
C5—C6	1.521 (4)	C14—C15	1.361 (5)
C6—N3	1.463 (3)	C14—H14	0.9300
C6—C11	1.521 (4)	C15—C16	1.382 (4)
C6—H6	0.9800	C15—H15	0.9300
C7—Cl1	1.780 (3)	C16—H16	0.9300
C7—H7A	0.9700

C2—S1—C1	99.99 (15)	C4—C7—H7B	109.7
C8—O1—C9	116.3 (2)	Cl1—C7—H7B	109.7
C2—N1—N3	101.5 (2)	H7A—C7—H7B	108.2
C3—N2—C2	101.5 (2)	O2—C8—O1	122.2 (3)
C3—N3—N1	109.8 (2)	O2—C8—C5	127.1 (3)
C3—N3—C6	127.0 (2)	O1—C8—C5	110.6 (2)
N1—N3—C6	122.9 (2)	O1—C9—C10	108.3 (2)
C3—N4—C4	119.2 (2)	O1—C9—H9A	110.0
C3—N4—H4	121 (2)	C10—C9—H9A	110.0
C4—N4—H4	118 (2)	O1—C9—H9B	110.0
S1—C1—H1A	109.5	C10—C9—H9B	110.0
S1—C1—H1B	109.5	H9A—C9—H9B	108.4
H1A—C1—H1B	109.5	C9—C10—H10A	109.5
S1—C1—H1C	109.5	C9—C10—H10B	109.5
H1A—C1—H1C	109.5	H10A—C10—H10B	109.5
H1B—C1—H1C	109.5	C9—C10—H10C	109.5
N1—C2—N2	115.8 (2)	H10A—C10—H10C	109.5
N1—C2—S1	124.5 (2)	H10B—C10—H10C	109.5
N2—C2—S1	119.64 (19)	C16—C11—C12	118.2 (3)
N3—C3—N2	111.5 (2)	C16—C11—C6	120.1 (3)
N3—C3—N4	120.3 (2)	C12—C11—C6	121.7 (2)
N2—C3—N4	128.2 (2)	C11—C12—C13	120.5 (3)
C5—C4—N4	121.2 (2)	C11—C12—H12	119.8
C5—C4—C7	125.8 (3)	C13—C12—H12	119.8
N4—C4—C7	113.0 (2)	C14—C13—C12	120.3 (3)
C4—C5—C8	121.9 (2)	C14—C13—H13	119.9
C4—C5—C6	122.5 (2)	C12—C13—H13	119.9
C8—C5—C6	115.5 (2)	C13—C14—C15	120.2 (3)
N3—C6—C11	111.1 (2)	C13—C14—H14	119.9
N3—C6—C5	106.7 (2)	C15—C14—H14	119.9
C11—C6—C5	112.6 (2)	C14—C15—C16	119.7 (3)
N3—C6—H6	108.8	C14—C15—H15	120.2
C11—C6—H6	108.8	C16—C15—H15	120.2
C5—C6—H6	108.8	C11—C16—C15	121.3 (3)
C4—C7—Cl1	109.7 (2)	C11—C16—H16	119.4
C4—C7—H7A	109.7	C15—C16—H16	119.4
Cl1—C7—H7A	109.7

N4—C4—C5—C8	179.2 (3)	N2—C2—N1—N3	1.7 (3)
C7—C4—C5—C8	−3.1 (4)	S1—C2—N1—N3	−177.30 (19)
N4—C4—C5—C6	3.4 (4)	N3—C3—N2—C2	0.4 (3)
C7—C4—C5—C6	−179.0 (3)	N4—C3—N2—C2	−177.2 (3)
C4—C5—C6—N3	−15.7 (4)	N1—C2—N2—C3	−1.3 (3)
C8—C5—C6—N3	168.2 (2)	S1—C2—N2—C3	177.67 (19)
C4—C5—C6—C11	106.4 (3)	N2—C3—N3—N1	0.6 (3)
C8—C5—C6—C11	−69.7 (3)	N4—C3—N3—N1	178.4 (2)
C5—C4—C7—Cl1	−102.2 (3)	N2—C3—N3—C6	174.0 (2)
N4—C4—C7—Cl1	75.7 (3)	N4—C3—N3—C6	−8.2 (4)
C4—C5—C8—O2	−18.9 (5)	C2—N1—N3—C3	−1.3 (3)
C6—C5—C8—O2	157.3 (3)	C2—N1—N3—C6	−175.0 (2)
C4—C5—C8—O1	163.3 (3)	C11—C6—N3—C3	−104.4 (3)
C6—C5—C8—O1	−20.5 (3)	C5—C6—N3—C3	18.7 (4)
N3—C6—C11—C16	−135.1 (3)	C11—C6—N3—N1	68.2 (3)
C5—C6—C11—C16	105.3 (3)	C5—C6—N3—N1	−168.8 (2)
N3—C6—C11—C12	47.4 (4)	N3—C3—N4—C4	−7.7 (4)
C5—C6—C11—C12	−72.2 (3)	N2—C3—N4—C4	169.7 (3)
C16—C11—C12—C13	0.7 (5)	C5—C4—N4—C3	9.7 (4)
C6—C11—C12—C13	178.2 (3)	C7—C4—N4—C3	−168.2 (2)
C11—C12—C13—C14	−0.7 (6)	O2—C8—O1—C9	−4.6 (4)
C12—C13—C14—C15	0.4 (6)	C5—C8—O1—C9	173.3 (2)
C13—C14—C15—C16	0.0 (6)	C10—C9—O1—C8	−173.8 (2)
C12—C11—C16—C15	−0.3 (5)	N1—C2—S1—C1	10.4 (3)
C6—C11—C16—C15	−177.8 (3)	N2—C2—S1—C1	−168.5 (3)
C14—C15—C16—C11	−0.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N2ⁱ	0.85 (3)	2.11 (3)	2.939 (3)	164 (3)
C7—H7B···O2	0.97	2.15	2.888 (4)	132

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇ClN₄O₂S
M_r	364.85
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	8.9280 (8), 9.8217 (9), 11.3775 (10)
α, β, γ (°)	106.022 (2), 102.631 (2), 109.919 (2)
V (Å³)	845.85 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.20 × 0.10 × 0.02

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6662, 3281, 2295
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.156, 1.02
No. of reflections	3281
No. of parameters	222
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.42

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Bruker, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N2ⁱ	0.85 (3)	2.11 (3)	2.939 (3)	164 (3)
C7—H7B···O2	0.97	2.15	2.888 (4)	132.0

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

The present work was supported by the National NSFC (grant Nos. 20572030, 20432010 and 20528201), the Cultivation Fund of the Key Scientific and Technical Innovation Project, Ministry of Education of China (grant No. 705039), and the Program for Excellent Research Groups of Hubei Province (grant No. 2004ABC002).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bruker (2001). SHELXTL (Version 6.12), SMART (Version 5.628) and SAINT (Version 6.45). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fedorova, O. V., Zhidovinova, M. S., Rusinov, G. L. & Ovchinnikova, I. G. (2003). Russ. Chem. Bull. Int. Ed. 52, 1768–1769. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 5-chloro­methyl-2-methyl­sulfanyl-7-phenyl-4,7-di­hydro-1,2,4-triazolo[1,5-a]pyrimidine-6-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 5-chloromethyl-2-methylsulfanyl-7-phenyl-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine-6-carboxylate