4-Methyl-7-[2-(1H-1,2,4-triazol-1-yl)eth­oxy]-2H-chromen-2-one

Zhang, Y.-Y.; Shi, Y.; Zhou, C.-H.

doi:10.1107/S1600536811009159

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o892

doi:10.1107/S1600536811009159

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4-Methyl-7-[2-(1H-1,2,4-triazol-1-yl)ethoxy]-2H-chromen-2-one

Yi-Yi Zhang,^a Yuan Shi ^a and Cheng-He Zhou ^a ^*

^aLaboratory of Bioorganic and Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China
^*Correspondence e-mail: zhouch@swu.edu.cn

(Received 3 March 2011; accepted 10 March 2011; online 15 March 2011)

In the title molecule, C₁₄H₁₃N₃O₃, the dihedral angle between the triazole ring and coumarin ring system is 73.01 (4)°. The crystal structure is stabilized by weak intermolecular C—H⋯N and C—H⋯O hydrogen bonds.

Related literature

For the pharmacological activity of coumarins, see: Wu et al. (2009 ). For details of the synthesis, see: Shi & Zhou (2011 ).

Experimental

Crystal data

C₁₄H₁₃N₃O₃
M_r = 271.27
Monoclinic, P 2₁ /n
a = 11.9861 (17) Å
b = 7.7090 (11) Å
c = 14.132 (2) Å
β = 101.034 (2)°
V = 1281.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.40 × 0.30 × 0.24 mm

Data collection

Bruker SMART CCD diffractometer
6501 measured reflections
2390 independent reflections
2134 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.097
S = 1.04
2390 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯N2ⁱ	0.95	2.56	3.453 (2)	157
C9—H9⋯N3ⁱⁱ	0.95	2.49	3.380 (2)	157
C13—H13⋯O1ⁱⁱⁱ	0.95	2.48	3.408 (2)	165
C13—H13⋯O2ⁱⁱⁱ	0.95	2.59	3.410 (2)	144
C14—H14⋯O3^iv	0.95	2.55	3.481 (2)	166
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) x, y+1, z.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811009159/lh5217sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009159/lh5217Isup2.hkl

checkCIF report

Comment top

Coumarins and their derivatives have attracted considerable attention due to their extensively biological activities such as antibacterial, antifungal, antiviral, anti-tubercular, anti-malarial, anticoagulant, anti-inflammatory, anticancer and antioxidant properties (Wu, et al., 2009; Shi, et al., 2011). In view of the therapeutic potentials of coumarins, we synthesized the title compound (I). Herein we report its crystal structure.

The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the triazole ring and coumarin ring system is 73.01 (4)°. The crystal structure is stabilized by weak intermolecular C—H···N and C—H···O hydrogen bonds.

Related literature top

For the pharmacological activity of coumarins, see: Wu et al. (2009). For details of the synthesis, see: Shi & Zhou (2011).

Experimental top

Compound (I) was synthesized according to the procedure of Shi & Zhou (2011). Single crystals were grown by slow evaporation of a solution of (I) in CDCl₃ at room temperature.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with displacement ellipsoids are drawn at the 50% probability level.

4-Methyl-7-[2-(1H-1,2,4-triazol-1-yl)ethoxy]-2H-chromen-2-one top

Crystal data top

C₁₄H₁₃N₃O₃	F(000) = 568
M_r = 271.27	D_x = 1.406 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3660 reflections
a = 11.9861 (17) Å	θ = 2.5–28.1°
b = 7.7090 (11) Å	µ = 0.10 mm⁻¹
c = 14.132 (2) Å	T = 173 K
β = 101.034 (2)°	Block, colourless
V = 1281.7 (3) Å³	0.40 × 0.30 × 0.24 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2134 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 25.5°, θ_min = 2.0°
ϕ and ω scans	h = −14→14
6501 measured reflections	k = −9→9
2390 independent reflections	l = −17→14

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0489P)² + 0.3468P] where P = (F_o² + 2F_c²)/3
2390 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₄H₁₃N₃O₃	V = 1281.7 (3) Å³
M_r = 271.27	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.9861 (17) Å	µ = 0.10 mm⁻¹
b = 7.7090 (11) Å	T = 173 K
c = 14.132 (2) Å	0.40 × 0.30 × 0.24 mm
β = 101.034 (2)°

Data collection top

Bruker SMART CCD diffractometer	2134 reflections with I > 2σ(I)
6501 measured reflections	R_int = 0.025
2390 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.04	Δρ_max = 0.16 e Å⁻³
2390 reflections	Δρ_min = −0.23 e Å⁻³
182 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
C1	0.34092 (11)	0.63715 (16)	1.03382 (10)	0.0285 (3)
C2	0.44570 (12)	0.61742 (16)	1.10231 (10)	0.0291 (3)
H2	0.4448	0.5553	1.1602	0.035*
C3	0.54494 (11)	0.68343 (16)	1.08755 (9)	0.0261 (3)
C4	0.54683 (10)	0.77458 (15)	0.99847 (9)	0.0228 (3)
C5	0.44581 (10)	0.78927 (15)	0.93081 (9)	0.0222 (3)
C6	0.43918 (10)	0.87313 (15)	0.84385 (9)	0.0233 (3)
H6	0.3692	0.8796	0.7992	0.028*
C7	0.53705 (11)	0.94803 (15)	0.82283 (9)	0.0232 (3)
C8	0.64008 (10)	0.93534 (16)	0.88806 (10)	0.0258 (3)
H8	0.7071	0.9852	0.8732	0.031*
C9	0.64365 (11)	0.84983 (16)	0.97420 (10)	0.0258 (3)
H9	0.7140	0.8418	1.0184	0.031*
C10	0.65229 (12)	0.66473 (19)	1.16165 (10)	0.0351 (3)
H10A	0.6375	0.5922	1.2149	0.053*
H10B	0.6783	0.7795	1.1864	0.053*
H10C	0.7111	0.6103	1.1320	0.053*
C11	0.62329 (11)	1.10015 (17)	0.70725 (10)	0.0296 (3)
H11A	0.6776	1.0054	0.7024	0.036*
H11B	0.6612	1.1859	0.7549	0.036*
C12	0.58548 (13)	1.18489 (17)	0.61091 (10)	0.0326 (3)
H12A	0.6525	1.2038	0.5807	0.039*
H12B	0.5330	1.1058	0.5687	0.039*
C13	0.42086 (12)	1.3931 (2)	0.58744 (11)	0.0379 (4)
H13	0.3631	1.3152	0.5581	0.046*
C14	0.50929 (12)	1.61203 (18)	0.64494 (10)	0.0328 (3)
H14	0.5252	1.7284	0.6651	0.039*
N1	0.52866 (9)	1.35020 (14)	0.61733 (8)	0.0256 (3)
N2	0.58838 (9)	1.49167 (14)	0.65533 (8)	0.0308 (3)
N3	0.40436 (11)	1.55923 (18)	0.60384 (10)	0.0440 (3)
O1	0.24796 (9)	0.58794 (14)	1.04329 (8)	0.0415 (3)
O2	0.34566 (7)	0.71985 (11)	0.94832 (6)	0.0267 (2)
O3	0.52351 (8)	1.03232 (12)	0.73646 (6)	0.0278 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0340 (7)	0.0207 (6)	0.0344 (8)	−0.0007 (5)	0.0152 (6)	0.0017 (5)
C2	0.0418 (8)	0.0215 (6)	0.0263 (7)	0.0029 (5)	0.0123 (6)	0.0015 (5)
C3	0.0347 (7)	0.0188 (6)	0.0253 (7)	0.0038 (5)	0.0067 (5)	−0.0041 (5)
C4	0.0271 (6)	0.0177 (6)	0.0240 (6)	0.0019 (5)	0.0060 (5)	−0.0036 (5)
C5	0.0232 (6)	0.0173 (6)	0.0281 (7)	−0.0012 (5)	0.0097 (5)	−0.0029 (5)
C6	0.0228 (6)	0.0220 (6)	0.0247 (7)	0.0005 (5)	0.0035 (5)	−0.0021 (5)
C7	0.0290 (6)	0.0181 (6)	0.0243 (7)	0.0014 (5)	0.0094 (5)	−0.0020 (5)
C8	0.0227 (6)	0.0231 (6)	0.0335 (7)	−0.0014 (5)	0.0100 (5)	−0.0023 (5)
C9	0.0233 (6)	0.0229 (6)	0.0302 (7)	0.0017 (5)	0.0031 (5)	−0.0035 (5)
C10	0.0429 (8)	0.0334 (8)	0.0268 (7)	0.0034 (6)	0.0009 (6)	0.0019 (6)
C11	0.0320 (7)	0.0241 (6)	0.0371 (8)	0.0015 (5)	0.0175 (6)	0.0023 (6)
C12	0.0465 (8)	0.0242 (7)	0.0321 (8)	0.0010 (6)	0.0205 (6)	−0.0015 (6)
C13	0.0297 (7)	0.0448 (9)	0.0377 (8)	−0.0036 (6)	0.0025 (6)	−0.0003 (7)
C14	0.0435 (8)	0.0268 (7)	0.0289 (7)	0.0043 (6)	0.0090 (6)	−0.0007 (6)
N1	0.0294 (6)	0.0252 (5)	0.0238 (6)	−0.0027 (4)	0.0093 (4)	−0.0006 (4)
N2	0.0309 (6)	0.0274 (6)	0.0341 (6)	−0.0019 (5)	0.0061 (5)	−0.0039 (5)
N3	0.0365 (7)	0.0479 (8)	0.0460 (8)	0.0129 (6)	0.0040 (6)	0.0032 (6)
O1	0.0359 (6)	0.0416 (6)	0.0514 (7)	−0.0049 (5)	0.0192 (5)	0.0119 (5)
O2	0.0243 (5)	0.0264 (5)	0.0305 (5)	−0.0035 (4)	0.0083 (4)	0.0031 (4)
O3	0.0305 (5)	0.0279 (5)	0.0266 (5)	−0.0017 (4)	0.0094 (4)	0.0039 (4)

Geometric parameters (Å, º) top

C1—O1	1.2085 (16)	C10—H10A	0.9800
C1—O2	1.3769 (16)	C10—H10B	0.9800
C1—C2	1.439 (2)	C10—H10C	0.9800
C2—C3	1.3463 (19)	C11—O3	1.4364 (15)
C2—H2	0.9500	C11—C12	1.500 (2)
C3—C4	1.4457 (18)	C11—H11A	0.9900
C3—C10	1.5023 (19)	C11—H11B	0.9900
C4—C5	1.3964 (18)	C12—N1	1.4560 (17)
C4—C9	1.3975 (17)	C12—H12A	0.9900
C5—C6	1.3774 (18)	C12—H12B	0.9900
C5—O2	1.3793 (14)	C13—N1	1.3223 (18)
C6—C7	1.3896 (17)	C13—N3	1.323 (2)
C6—H6	0.9500	C13—H13	0.9500
C7—O3	1.3647 (15)	C14—N2	1.3145 (17)
C7—C8	1.3960 (18)	C14—N3	1.344 (2)
C8—C9	1.3778 (19)	C14—H14	0.9500
C8—H8	0.9500	N1—N2	1.3576 (15)
C9—H9	0.9500

O1—C1—O2	115.86 (12)	H10A—C10—H10B	109.5
O1—C1—C2	126.63 (13)	C3—C10—H10C	109.5
O2—C1—C2	117.50 (11)	H10A—C10—H10C	109.5
C3—C2—C1	122.62 (12)	H10B—C10—H10C	109.5
C3—C2—H2	118.7	O3—C11—C12	107.20 (11)
C1—C2—H2	118.7	O3—C11—H11A	110.3
C2—C3—C4	118.69 (12)	C12—C11—H11A	110.3
C2—C3—C10	121.34 (13)	O3—C11—H11B	110.3
C4—C3—C10	119.97 (12)	C12—C11—H11B	110.3
C5—C4—C9	116.76 (12)	H11A—C11—H11B	108.5
C5—C4—C3	118.66 (11)	N1—C12—C11	112.86 (11)
C9—C4—C3	124.58 (12)	N1—C12—H12A	109.0
C6—C5—O2	116.01 (11)	C11—C12—H12A	109.0
C6—C5—C4	122.92 (11)	N1—C12—H12B	109.0
O2—C5—C4	121.07 (11)	C11—C12—H12B	109.0
C5—C6—C7	118.60 (11)	H12A—C12—H12B	107.8
C5—C6—H6	120.7	N1—C13—N3	110.86 (13)
C7—C6—H6	120.7	N1—C13—H13	124.6
O3—C7—C6	115.36 (11)	N3—C13—H13	124.6
O3—C7—C8	124.24 (11)	N2—C14—N3	115.46 (13)
C6—C7—C8	120.40 (12)	N2—C14—H14	122.3
C9—C8—C7	119.40 (11)	N3—C14—H14	122.3
C9—C8—H8	120.3	C13—N1—N2	109.53 (11)
C7—C8—H8	120.3	C13—N1—C12	129.74 (12)
C8—C9—C4	121.91 (12)	N2—N1—C12	120.68 (11)
C8—C9—H9	119.0	C14—N2—N1	102.03 (11)
C4—C9—H9	119.0	C13—N3—C14	102.12 (12)
C3—C10—H10A	109.5	C1—O2—C5	121.37 (10)
C3—C10—H10B	109.5	C7—O3—C11	117.86 (10)

O1—C1—C2—C3	−176.91 (13)	C5—C4—C9—C8	0.34 (18)
O2—C1—C2—C3	3.28 (19)	C3—C4—C9—C8	−179.93 (11)
C1—C2—C3—C4	−1.36 (19)	O3—C11—C12—N1	74.23 (14)
C1—C2—C3—C10	178.33 (12)	N3—C13—N1—N2	−0.17 (17)
C2—C3—C4—C5	−0.56 (17)	N3—C13—N1—C12	−177.64 (13)
C10—C3—C4—C5	179.75 (11)	C11—C12—N1—C13	−111.33 (16)
C2—C3—C4—C9	179.72 (12)	C11—C12—N1—N2	71.44 (15)
C10—C3—C4—C9	0.02 (18)	N3—C14—N2—N1	0.17 (16)
C9—C4—C5—C6	−0.06 (18)	C13—N1—N2—C14	0.00 (15)
C3—C4—C5—C6	−179.80 (11)	C12—N1—N2—C14	177.75 (11)
C9—C4—C5—O2	−179.74 (10)	N1—C13—N3—C14	0.25 (16)
C3—C4—C5—O2	0.51 (17)	N2—C14—N3—C13	−0.26 (17)
O2—C5—C6—C7	179.02 (10)	O1—C1—O2—C5	176.87 (11)
C4—C5—C6—C7	−0.68 (18)	C2—C1—O2—C5	−3.29 (17)
C5—C6—C7—O3	−178.52 (10)	C6—C5—O2—C1	−178.20 (11)
C5—C6—C7—C8	1.15 (18)	C4—C5—O2—C1	1.50 (17)
O3—C7—C8—C9	178.75 (11)	C6—C7—O3—C11	−175.04 (10)
C6—C7—C8—C9	−0.89 (18)	C8—C7—O3—C11	5.30 (17)
C7—C8—C9—C4	0.13 (19)	C12—C11—O3—C7	179.81 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N2ⁱ	0.95	2.56	3.453 (2)	157
C9—H9···N3ⁱⁱ	0.95	2.49	3.380 (2)	157
C13—H13···O1ⁱⁱⁱ	0.95	2.48	3.408 (2)	165
C13—H13···O2ⁱⁱⁱ	0.95	2.59	3.410 (2)	144
C14—H14···O3^iv	0.95	2.55	3.481 (2)	166

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x+1/2, −y+5/2, z+1/2; (iii) −x+1/2, y+1/2, −z+3/2; (iv) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃N₃O₃
M_r	271.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	11.9861 (17), 7.7090 (11), 14.132 (2)
β (°)	101.034 (2)
V (Å³)	1281.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.30 × 0.24

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6501, 2390, 2134
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.097, 1.04
No. of reflections	2390
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.23

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N2ⁱ	0.95	2.56	3.453 (2)	157
C9—H9···N3ⁱⁱ	0.95	2.49	3.380 (2)	157
C13—H13···O1ⁱⁱⁱ	0.95	2.48	3.408 (2)	165
C13—H13···O2ⁱⁱⁱ	0.95	2.59	3.410 (2)	144
C14—H14···O3^iv	0.95	2.55	3.481 (2)	166

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x+1/2, −y+5/2, z+1/2; (iii) −x+1/2, y+1/2, −z+3/2; (iv) x, y+1, z.

Acknowledgements

The authors thank Southwest University (grant Nos. SWUB2006018, XSGX0602 and SWUF2007023) and the Natural Science Foundation of Chongqing (grant No. 2007BB5369) for financial support.

References

Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, Y. & Zhou, C. H. (2011). Bioorg. Med. Chem. Lett. 21, 956–960. Web of Science CrossRef CAS PubMed Google Scholar
Wu, L., Wang, X., Xu, W., Farzaneh, F. & Xu, R. (2009). Curr. Med. Chem. 16, 4236–4260. Web of Science CrossRef PubMed CAS Google Scholar