1-Benzyl-4-(naphthalen-1-yl)-1H-1,2,3-triazole

Sarmiento-Sánchez, J.I.; Aguirre, G.; Rivero, I.A.

doi:10.1107/S1600536811019994

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1856

doi:10.1107/S1600536811019994

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1-Benzyl-4-(naphthalen-1-yl)-1H-1,2,3-triazole

Juan I. Sarmiento-Sánchez,^a Gerardo Aguirre ^a and Ignacio A. Rivero ^a ^*

^aCentro de Graduados e Investigación del Instituto Tecnológico de Tijuana, Apdo. Postal 1166, 22500 Tijuana, BC, Mexico
^*Correspondence e-mail: iarivero@yahoo.com.mx

(Received 12 January 2011; accepted 26 May 2011; online 30 June 2011)

In the title compound, C₁₉H₁₅N₃, the benzyl group is almost perpendicular to the triazole ring [dihedral angle = 80.64 (8)°], while the napthyl group makes an angle of 30.27 (12)° with the plane of the triazole ring. This conformation is different from the 1-benzyl-4-phenyl-1H-1,2,3-triazole analogue, which has the benzyl ring system at an angle of 87.94° and the phenyl group at an angle of 3.35° to the plane of the triazole ring.

Related literature

For the biological activity of triazoles, see: Alvarez et al. (1994 ); Brockunier et al. (2000 ); Genin et al. (2000 ); Katritsky et al. (1996 ). For related structures, see: Bi (2010 ); Huang et al. (2010 ); Jabli et al. (2010 ); Key et al. (2008 ); Makam & Yulin (2004 ); Santos-Contreras et al. (2009 ): Vaqueiro (2006 ).

Experimental

Crystal data

C₁₉H₁₅N₃
M_r = 285.34
Monoclinic, P 2₁ /c
a = 9.896 (2) Å
b = 11.038 (3) Å
c = 14.136 (4) Å
β = 102.701 (13)°
V = 1506.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.5 × 0.48 × 0.28 mm

Data collection

Siemens P4 diffractometer
3663 measured reflections
3471 independent reflections
1730 reflections with I > 2σ(I)
R_int = 0.028
3 standard reflections every 97 reflections intensity decay: 5.4%

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.202
S = 1.01
3471 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: XSCANS (Siemens, 1996 ); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019994/fl2334sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019994/fl2334Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811019994/fl2334Isup3.cml

checkCIF report

Comment top

In recent years, triazole compounds have received much attention due to their wide range of applications in organic and medicinal chemistry. Specifically, 1,2,3-triazoles have been used in pharmaceuticals, agrochemicals, dyes, photographic materials and corrosion inhibitors (Katritsky et al., 1996). There are numerous examples in the literature of the biological activity of triazole compounds acting as as anti-HIV agents (Alvarez et al., 1994) or as antibiotics due to their antimicrobial activity against Gram positive bacteria (Genin et al., 2000) and as selective β₃ adrenergic agonist receptors (Brockunier et al., 2000).

The molecular structure of (I) is shown in Fig. 1. The molecule shows that the phenyl group and the triazole heterocycle are linked by the methylene group. The carbon atom C13 with a C14—C13—N1 angle of 112.5 (2)^o is distorted from ideal tetrahedral geometry (109.7¯). This can be attributed to steric factors of adjacent cyclic systems. Also, the bonds distances N3—C11, C11—C12, C12—N1, N1—N2 and N2—N3 are 1.353 (3), 1.353 (4), 1.335 (3), 1.337 (3) and 1.321 (3) Å, respectively, which agree with the C═C, N═N and C—N distances found in the literature for compounds having triazole heterocycles (Huang et al., 2010; Jabli et al., 2010; Key et al. 2008). In addition, C12—N1 and C11—N3 are significantly shorter that the C—N single bonds (1.47 Å) (Vaqueiro, 2006; Bi, 2010) but longer than true C—N double bonds (1.28 Å) (Santos-Contreras et al., 2009). This indicates a delocalization of electrons in the triazolyl system.

As shown in Fig. 1, the molecule shows the benzyl group is located above the plane of the triazole at a dihedral angle of 80.64 (0.08)° and the naphthyl group is at an angle fo 30.27 (0.12)°. This conformation is different from its analogue 1-benzyl-4-phenyl-1H-1, 2,3-triazole which presents the benzyl at an dihedral angle of 87.94° and the phenyl at an angle of 3.35° to the plane of the triazole (Makam & Yulin, 2004).

Related literature top

For the biological activity of triazoles, see: Alvarez et al. (1994); Brockunier et al. (2000); Genin et al. (2000); Katritsky et al. (1996). For related structures, see: Bi (2010); Huang et al. (2010); Jabli et al. (2010); Key et al. (2008); Makam & Yulin (2004); Santos-Contreras et al. (2009): Vaqueiro (2006).

Experimental top

Experimental

All reagents were purchased in the highest quality available and were used without further purification. The solvents used in column chromatography were obtained from commercial suppliers and used without distillation. To a solution tert-BuOH/H₂O (6 ml 1:1 v/v) was added benzyl bromide (1.684 mmol), sodium azide (1.684 mmol), 1-ethynyl-naphthalene (1.684 mmol), copper(II) sulfate (0.084 mmol, 5% mol) and sodium ascorbate (0.168 mmol, 10% mol) with vigorous stirring at 60 °C for 8 h. The reaction mixture was filtered with diatomaceous earth (kieselguhr) or zeolite and silica gel in vacuo, then extracted with ethyl acetate (60 ml). The extracts were combined and dried over anhydrous sodium sulfate. After evaporation of the solvent, the residual oil solidified and was purified by flash chromatography to give (I) (petroleum ether/EtOAc 1:1 v/v). Yield 85%; pale yellow solid; mp 89–90 °C; ¹H-NMR (CDCl₃, 200 MHz): δ 8.39–8.34 (m, 1H), 7.88–7.82 (m, 2H), 7.71 (s, 1H), 7.69–7.66 (d, J = 7.33 Hz, 1H), 7.52–7.47 (dd, J = 6.42, 3.48 Hz, 4H), 7.37–7.36 (d, J = 1.83 Hz, 4H), 5.61 (s, 2H); ¹³C-NMR (CDCl₃, 50 MHz): δ 147.3, 134.6, 133.8, 131.0, 129.1, 128.8, 128.7, 128.3, 128.0, 127.1, 126.5, 125.9, 125.4, 125.2, 122.4, 54.1; IR (KBr, pellet): 1686, 1601, 1454 cm^-1; ESI-MS m/z: 286 [M+H]⁺, 308 [M+Na]⁺, 324 [M+K]⁺, 593 [2M+Na]⁺.

Crystallization

50 mg of (I) compound was placed for diffusion in a glass vial with chloroform-petroleum ether for one day. The crystals, suitable for data collection, were separated by filtration.

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS (Siemens, 1996); data reduction: XSCANS (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The title compound (I) with displacement ellipsoids drawn at 30% probability level.

1-Benzyl-4-(naphthalen-1-yl)-1H-1,2,3-triazole top

Crystal data top

C₁₉H₁₅N₃	F(000) = 600
M_r = 285.34	D_x = 1.258 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 36 reflections
a = 9.896 (2) Å	θ = 4.6–12.4°
b = 11.038 (3) Å	µ = 0.08 mm⁻¹
c = 14.136 (4) Å	T = 298 K
β = 102.701 (13)°	Prismatic, colorless
V = 1506.2 (6) Å³	0.5 × 0.48 × 0.28 mm
Z = 4

Data collection top

Siemens P4 diffractometer	R_int = 0.028
Radiation source: fine-focus sealed tube	θ_max = 27.5°, θ_min = 2.1°
Graphite monochromator	h = 0→12
2θ/ω scans	k = 0→14
3663 measured reflections	l = −18→17
3471 independent reflections	3 standard reflections every 97 reflections
1730 reflections with I > 2σ(I)	intensity decay: 5.4%

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.202	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0839P)² + 0.308P] where P = (F_o² + 2F_c²)/3
3471 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₉H₁₅N₃	V = 1506.2 (6) Å³
M_r = 285.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.896 (2) Å	µ = 0.08 mm⁻¹
b = 11.038 (3) Å	T = 298 K
c = 14.136 (4) Å	0.5 × 0.48 × 0.28 mm
β = 102.701 (13)°

Data collection top

Siemens P4 diffractometer	R_int = 0.028
3663 measured reflections	3 standard reflections every 97 reflections
3471 independent reflections	intensity decay: 5.4%
1730 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.202	H-atom parameters constrained
S = 1.01	Δρ_max = 0.40 e Å⁻³
3471 reflections	Δρ_min = −0.17 e Å⁻³
199 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
N1	0.2899 (2)	0.3968 (2)	0.18018 (16)	0.0603 (7)
N2	0.3058 (3)	0.2778 (3)	0.19682 (18)	0.0688 (7)
N3	0.4044 (3)	0.2660 (2)	0.27619 (18)	0.0665 (7)
C1	0.5662 (3)	0.4031 (3)	0.39312 (19)	0.0548 (7)
C2	0.6434 (3)	0.5043 (3)	0.3915 (2)	0.0688 (9)
H2B	0.6208	0.5550	0.3377	0.083*
C3	0.7552 (4)	0.5365 (3)	0.4664 (2)	0.0779 (10)
H3B	0.8053	0.6066	0.4613	0.093*
C4	0.7905 (4)	0.4661 (3)	0.5459 (2)	0.0773 (10)
H4A	0.8655	0.4870	0.5954	0.093*
C5	0.7114 (3)	0.3581 (3)	0.55387 (19)	0.0592 (8)
C6	0.7469 (4)	0.2850 (3)	0.6363 (2)	0.0756 (10)
H6A	0.8207	0.3068	0.6864	0.091*
C7	0.6745 (4)	0.1828 (3)	0.6434 (2)	0.0779 (10)
H7A	0.6995	0.1339	0.6981	0.093*
C8	0.5616 (3)	0.1501 (3)	0.5686 (2)	0.0726 (9)
H8A	0.5123	0.0799	0.5748	0.087*
C9	0.5231 (3)	0.2188 (3)	0.4877 (2)	0.0657 (8)
H9A	0.4475	0.1958	0.4394	0.079*
C10	0.5991 (3)	0.3282 (2)	0.47587 (18)	0.0519 (7)
C11	0.4501 (3)	0.3772 (3)	0.30902 (19)	0.0530 (7)
C12	0.3770 (3)	0.4599 (3)	0.2479 (2)	0.0627 (8)
H12A	0.3856	0.5438	0.2521	0.075*
C13	0.1908 (3)	0.4396 (4)	0.0935 (2)	0.0837 (11)
H13A	0.1334	0.3723	0.0644	0.100*
H13B	0.2413	0.4688	0.0465	0.100*
C14	0.0994 (3)	0.5392 (3)	0.11590 (18)	0.0559 (7)
C15	0.1201 (3)	0.6574 (3)	0.0925 (2)	0.0713 (9)
H15A	0.1931	0.6762	0.0634	0.086*
C16	0.0351 (4)	0.7485 (3)	0.1112 (2)	0.0768 (10)
H16A	0.0509	0.8280	0.0946	0.092*
C17	−0.0723 (3)	0.7230 (3)	0.1539 (2)	0.0687 (9)
H17A	−0.1301	0.7846	0.1664	0.082*
C18	−0.0945 (3)	0.6056 (3)	0.1783 (2)	0.0680 (9)
H18A	−0.1673	0.5875	0.2078	0.082*
C19	−0.0089 (3)	0.5140 (3)	0.1592 (2)	0.0617 (8)
H19A	−0.0247	0.4345	0.1759	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0498 (14)	0.0771 (18)	0.0486 (13)	0.0138 (13)	−0.0007 (11)	−0.0144 (12)
N2	0.0644 (16)	0.0719 (19)	0.0660 (16)	−0.0103 (14)	0.0052 (13)	−0.0132 (14)
N3	0.0671 (16)	0.0661 (17)	0.0624 (15)	−0.0031 (13)	0.0060 (13)	0.0003 (13)
C1	0.0597 (17)	0.0507 (17)	0.0522 (16)	0.0095 (14)	0.0082 (13)	−0.0086 (13)
C2	0.078 (2)	0.0553 (19)	0.0652 (19)	−0.0055 (17)	−0.0020 (16)	−0.0066 (15)
C3	0.093 (2)	0.0549 (19)	0.075 (2)	−0.0171 (17)	−0.0047 (19)	−0.0025 (17)
C4	0.083 (2)	0.069 (2)	0.068 (2)	−0.0057 (18)	−0.0085 (18)	−0.0155 (18)
C5	0.0637 (18)	0.0638 (19)	0.0460 (15)	0.0207 (15)	0.0033 (14)	−0.0046 (13)
C6	0.078 (2)	0.086 (3)	0.0567 (18)	0.023 (2)	0.0022 (17)	−0.0063 (17)
C7	0.084 (2)	0.083 (3)	0.067 (2)	0.021 (2)	0.0194 (19)	0.0096 (18)
C8	0.076 (2)	0.076 (2)	0.071 (2)	0.0046 (18)	0.0274 (18)	0.0163 (17)
C9	0.0626 (19)	0.069 (2)	0.0681 (19)	0.0069 (16)	0.0205 (15)	0.0056 (16)
C10	0.0551 (16)	0.0530 (16)	0.0463 (14)	0.0164 (14)	0.0085 (13)	−0.0066 (12)
C11	0.0507 (15)	0.0598 (18)	0.0459 (14)	0.0107 (13)	0.0049 (12)	−0.0105 (13)
C12	0.0637 (18)	0.0594 (18)	0.0568 (16)	0.0166 (15)	−0.0043 (14)	−0.0165 (14)
C13	0.068 (2)	0.126 (3)	0.0482 (17)	0.034 (2)	−0.0059 (15)	−0.0121 (18)
C14	0.0457 (15)	0.076 (2)	0.0414 (14)	0.0091 (14)	−0.0001 (12)	0.0008 (14)
C15	0.0512 (18)	0.098 (3)	0.0633 (19)	−0.0065 (18)	0.0092 (15)	0.0198 (18)
C16	0.080 (2)	0.067 (2)	0.074 (2)	−0.0104 (19)	−0.0025 (19)	0.0197 (17)
C17	0.068 (2)	0.063 (2)	0.0697 (19)	0.0095 (16)	0.0046 (17)	0.0042 (16)
C18	0.0528 (18)	0.081 (2)	0.075 (2)	−0.0010 (17)	0.0227 (16)	0.0033 (17)
C19	0.0641 (18)	0.0548 (18)	0.0645 (18)	−0.0021 (15)	0.0109 (15)	0.0042 (14)

Geometric parameters (Å, º) top

N1—C12	1.335 (3)	C8—C9	1.356 (4)
N1—N2	1.337 (3)	C8—H8A	0.9300
N1—C13	1.470 (3)	C9—C10	1.452 (4)
N2—N3	1.321 (3)	C9—H9A	0.9300
N3—C11	1.353 (3)	C11—C12	1.353 (4)
C1—C2	1.357 (4)	C12—H12A	0.9300
C1—C10	1.410 (4)	C13—C14	1.500 (4)
C1—C11	1.488 (4)	C13—H13A	0.9700
C2—C3	1.399 (4)	C13—H13B	0.9700
C2—H2B	0.9300	C14—C15	1.372 (4)
C3—C4	1.348 (4)	C14—C19	1.375 (4)
C3—H3B	0.9300	C15—C16	1.374 (5)
C4—C5	1.444 (5)	C15—H15A	0.9300
C4—H4A	0.9300	C16—C17	1.363 (5)
C5—C6	1.397 (4)	C16—H16A	0.9300
C5—C10	1.421 (4)	C17—C18	1.371 (4)
C6—C7	1.352 (5)	C17—H17A	0.9300
C6—H6A	0.9300	C18—C19	1.384 (4)
C7—C8	1.407 (5)	C18—H18A	0.9300
C7—H7A	0.9300	C19—H19A	0.9300

C12—N1—N2	110.8 (2)	C1—C10—C9	123.5 (3)
C12—N1—C13	129.6 (3)	C5—C10—C9	116.1 (3)
N2—N1—C13	119.6 (3)	C12—C11—N3	107.6 (2)
N3—N2—N1	106.4 (2)	C12—C11—C1	126.2 (3)
N2—N3—C11	109.3 (2)	N3—C11—C1	126.1 (3)
C2—C1—C10	117.9 (3)	N1—C12—C11	106.0 (3)
C2—C1—C11	118.9 (3)	N1—C12—H12A	127.0
C10—C1—C11	123.2 (3)	C11—C12—H12A	127.0
C1—C2—C3	123.4 (3)	N1—C13—C14	112.5 (2)
C1—C2—H2B	118.3	N1—C13—H13A	109.1
C3—C2—H2B	118.3	C14—C13—H13A	109.1
C4—C3—C2	120.1 (3)	N1—C13—H13B	109.1
C4—C3—H3B	120.0	C14—C13—H13B	109.1
C2—C3—H3B	120.0	H13A—C13—H13B	107.8
C3—C4—C5	119.7 (3)	C15—C14—C19	118.1 (3)
C3—C4—H4A	120.1	C15—C14—C13	121.1 (3)
C5—C4—H4A	120.1	C19—C14—C13	120.7 (3)
C6—C5—C10	121.6 (3)	C14—C15—C16	121.4 (3)
C6—C5—C4	120.0 (3)	C14—C15—H15A	119.3
C10—C5—C4	118.4 (3)	C16—C15—H15A	119.3
C7—C6—C5	120.3 (3)	C17—C16—C15	120.2 (3)
C7—C6—H6A	119.9	C17—C16—H16A	119.9
C5—C6—H6A	119.9	C15—C16—H16A	119.9
C6—C7—C8	120.3 (3)	C16—C17—C18	119.4 (3)
C6—C7—H7A	119.9	C16—C17—H17A	120.3
C8—C7—H7A	119.9	C18—C17—H17A	120.3
C9—C8—C7	121.4 (3)	C17—C18—C19	120.2 (3)
C9—C8—H8A	119.3	C17—C18—H18A	119.9
C7—C8—H8A	119.3	C19—C18—H18A	119.9
C8—C9—C10	120.4 (3)	C14—C19—C18	120.7 (3)
C8—C9—H9A	119.8	C14—C19—H19A	119.7
C10—C9—H9A	119.8	C18—C19—H19A	119.7
C1—C10—C5	120.4 (3)

C12—N1—N2—N3	0.0 (3)	C8—C9—C10—C5	−1.2 (4)
C13—N1—N2—N3	177.3 (2)	N2—N3—C11—C12	0.1 (3)
N1—N2—N3—C11	−0.1 (3)	N2—N3—C11—C1	−176.1 (2)
C10—C1—C2—C3	1.4 (5)	C2—C1—C11—C12	−27.0 (4)
C11—C1—C2—C3	−179.5 (3)	C10—C1—C11—C12	151.9 (3)
C1—C2—C3—C4	−0.6 (5)	C2—C1—C11—N3	148.4 (3)
C2—C3—C4—C5	−0.7 (5)	C10—C1—C11—N3	−32.6 (4)
C3—C4—C5—C6	−179.7 (3)	N2—N1—C12—C11	0.1 (3)
C3—C4—C5—C10	1.1 (5)	C13—N1—C12—C11	−176.9 (3)
C10—C5—C6—C7	0.2 (5)	N3—C11—C12—N1	−0.1 (3)
C4—C5—C6—C7	−179.0 (3)	C1—C11—C12—N1	176.0 (2)
C5—C6—C7—C8	−0.9 (5)	C12—N1—C13—C14	−50.4 (4)
C6—C7—C8—C9	0.5 (5)	N2—N1—C13—C14	132.8 (3)
C7—C8—C9—C10	0.6 (5)	N1—C13—C14—C15	104.8 (3)
C2—C1—C10—C5	−1.0 (4)	N1—C13—C14—C19	−76.2 (4)
C11—C1—C10—C5	−179.9 (2)	C19—C14—C15—C16	−0.3 (4)
C2—C1—C10—C9	178.7 (3)	C13—C14—C15—C16	178.7 (3)
C11—C1—C10—C9	−0.2 (4)	C14—C15—C16—C17	0.1 (5)
C6—C5—C10—C1	−179.5 (3)	C15—C16—C17—C18	0.2 (5)
C4—C5—C10—C1	−0.3 (4)	C16—C17—C18—C19	−0.3 (5)
C6—C5—C10—C9	0.8 (4)	C15—C14—C19—C18	0.2 (4)
C4—C5—C10—C9	−180.0 (3)	C13—C14—C19—C18	−178.8 (3)
C8—C9—C10—C1	179.1 (3)	C17—C18—C19—C14	0.1 (5)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅N₃
M_r	285.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.896 (2), 11.038 (3), 14.136 (4)
β (°)	102.701 (13)
V (Å³)	1506.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.5 × 0.48 × 0.28

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3663, 3471, 1730
R_int	0.028

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.202, 1.01
No. of reflections	3471
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.17

Computer programs: XSCANS (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006).

Acknowledgements

We gratefully acknowledge support of this project by the Consejo Nacional de Ciencia y Tecnología (CONACyT, grant No. SEP-2004-CO1–47835) and the Dirección General de Educación Superior Tecnológica (DGEST). JS thanks CONACYT for a graduate scholarship.

References

Alvarez, R., Elazquez, S. V., San, F., Aquaro, S., De, C., Perno, C. F., Karlesson, A., Balzarini, J. & Camarasa, M. J. (1994). J. Med. Chem. 37, 4185–4194. CrossRef CAS PubMed Web of Science Google Scholar
Bi, Y. (2010). Acta Cryst. E66, o951. Web of Science CrossRef IUCr Journals Google Scholar
Brockunier, L. L., Parmee, E. R., Ok, H. O., Candelore, M. R., Cascieri, M. A., Colwell, L. F., Deng, L., Feeney, W. P., Forest, M. J., Hom, G. J., MacIntyre, D. E., Tota, L., Wyvratt, M. J., Fisher, M. H. & Weber, A. E. (2000). Bioorg. Med. Chem. Lett. 10, 2111–2114. Web of Science CrossRef PubMed CAS Google Scholar
Genin, M. J., Allwine, D. A., Anderson, D. J., Barbachyn, M. R., Emmert, D. E., Garmon, S. A., Graber, D. R., Grega, K. C., Hester, J. B., Hutchinson, D. K., Morris, J., Reischer, R. J., Ford, C. W., Zurenco, G. E., Hamel, J. C., Schaadt, R. D., Stapertand, D. & Yagi, B. H. (2000). J. Med. Chem. 43, 953–970. Web of Science CrossRef PubMed CAS Google Scholar
Huang, C.-C., Wu, F.-L., Lo, Y. H., Lai, W.-R. & Lin, C.-H. (2010). Acta Cryst. E66, o1690. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jabli, H., Ouazzani Chahdi, F., Saffon, N., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o232. Web of Science CSD CrossRef IUCr Journals Google Scholar
Katritsky, A. R., Rees, C. W. & Scriven, C. W. V. (1996). Editors. Comprehensive Heterocyclic Chemistry II, Vol. 4, pp. 1–126. Oxford: Elsevier Science. Google Scholar
Key, J. A., Cairo, C. W. & Ferguson, M. J. (2008). Acta Cryst. E64, o1910. Web of Science CSD CrossRef IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Makam, S. R. & Yulin, L. (2004). Tetrahedron Lett. 45, 6129–6132. Google Scholar
Santos-Contreras, R. J., Ramos-Organillo, A., García-Báez, E. V., Padilla-Martínez, I. I. & Martínez-Martínez, F. J. (2009). Acta Cryst. C65, o8–o10. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Vaqueiro, P. (2006). Acta Cryst. E62, o2632–o2633. Web of Science CSD CrossRef IUCr Journals Google Scholar