(1-Phenyl-1H-1,2,3-triazol-4-yl)methyl pyridine-3-carboxyl­ate

Karimov, Z.; Abdugafurov, I.; Talipov, S.; Tashkhodjaev, B.

doi:10.1107/S1600536810021999

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1674

doi:10.1107/S1600536810021999

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(1-Phenyl-1H-1,2,3-triazol-4-yl)methyl pyridine-3-carboxylate

Zakirjon Karimov,^a ^* Ibrakhim Abdugafurov,^b Samat Talipov ^c and Bakhodir Tashkhodjaev ^d

^aTashkent Institute of Irrigation and Melioration, Qori-Niyoziy Str. 39, Tashkent 100000, Uzbekistan, ^bAndijan State University, Universitetskaja str. 129, Andijan 170100, Uzbekistan, ^cInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str,83, Tashkent 100125, Uzbekistan, and ^dS.Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, Uzbekistan
^*Correspondence e-mail: zokir_k@mail.ru

(Received 19 May 2010; accepted 8 June 2010; online 16 June 2010)

In the title compound, C₁₅H₁₂N₄O₂, the dihedral angle between the planes of the nicotinoyloxy fragment and triazole ring is 88.61 (5)°. The dihedral angle between the planes of triazole and benzene rings is 16.54 (11)°. The crystal structure is stabilized by intermolecular C—H⋯N, C—H⋯O and C—H⋯π(triazole) hydrogen bonds and aromatic π–π stacking interactions between the benzene and triazole rings [centroid–centroid distance = 3.895 (1) Å]

Related literature

For the synthesis of 1,2,3-triazole derivatives, see: Berestovitskaya et al. (2007 ); Piterskaya et al. (1996a ,b ). For their physiological activity, see: Contreras et al. (1978 ). For related structures, see: Berestovitskaya et al. (2007); Monkowius et al. (2007 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₂N₄O₂
M_r = 280.29
Monoclinic, P 2₁ /n
a = 5.5178 (5) Å
b = 23.650 (2) Å
c = 10.287 (2) Å
β = 91.841 (14)°
V = 1341.8 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.79 mm⁻¹
T = 293 K
0.70 × 0.45 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.674, T_max = 1.000
4791 measured reflections
2460 independent reflections
1877 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.124
S = 1.04
2460 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the triazole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯N1ⁱ	0.93	2.64	3.550 (3)	165
C2—H2⋯O1ⁱⁱ	0.93	2.71	3.464 (2)	139
C15—H15⋯O1ⁱⁱⁱ	0.93	2.68	3.559 (2)	158
C7—H7a⋯Cg1^iv	0.97	2.92	3.313 (2)	106
Symmetry codes: (i) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+2, -y, -z+1; (iv) -x+1, -y, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021999/kp2262sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021999/kp2262Isup2.hkl

checkCIF report

Comment top

Triazole derivatives possess different biological activities (Contreras et al. 1978). The title compound was synthesized with purpose of finding of a potential biological active compound.

The asymmetric unit contains one molecule of 1-phenyl-4-(nicotinoyloxymethyl)-1,2,3-triazole (Fig. 1). In the molecule nicotinoyloxy, phenyl groups and triazole system are planar, with r.m.s. deviations of 0.0075, 0.0048 and 0.0028 Å, respectively. Nicotinoyloxy fragment arranged nearly perpendicular to triazole ring. The angle between the planes of the nicotinoyloxy fragment and triazole ring is 88.61 (5)°. The angle between the planes of triazole and benzene rings is 16.54 (11)°. The observed structure is stabilized by C—H···N, C—H···O and C—H···π (triazole) type hydrogen bonds (Table 1) and aromatic π–π stacking interactions. A centrosymmetric π–π stacking interactions are observed between triazole group and benzene group of molecules at x,y,z and 1 - x, -y, 2 - z where the ring-centroid separation is 3.895 (1) Å, triazole centroid distance to benzene plane is 3.429 (1) Å with ring offset of 1.847 (1) Å (Fig. 2). The bond distances and angles in molecule are in normal ranges (Allen et al., 1987).

Related literature top

For the synthesis of 1,2,3-triazole derivatives, see: Berestovitskaya et al. (2007); Piterskaya et al. (1996a,b). For their physiological activity, see: Contreras et al. (1978). For related structures, see: Berestovitskaya et al. (2007); Monkowius et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

Mixture of 3-(nicotinoyloxy)-1-propyne (1.61 g, 0,01 mole) and fresh prepared phenylazide (1.310 g, 0,011 mole) in 30 ml toluen was heated with a backflow condenser for 6 h. Then it was cooled and precipitate were isolated by decantation. Obtained crystals were washed with ether and re-crystallized from toluen. It was obtained 78.3% yeild (2.19 g) of title compound, m.p. 96–97° C, R_f =0.53 (ether-hexane 9:1). Colorless crystals suitable for X-ray analysis were obtained from acetone by slow evaporation.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Displacement ellipsoid plot at the 50% probability level for the non-H atoms.
	Fig. 2. Part of the crystal structure showing a π–π stacking interactions observed between triazole and triazole rings.

(1-Phenyl-1H-1,2,3-triazol-4-yl)methyl pyridine-3-carboxylate top

Crystal data top

C₁₅H₁₂N₄O₂	F(000) = 584
M_r = 280.29	D_x = 1.388 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 370(2) K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.5418 Å
a = 5.5178 (5) Å	Cell parameters from 2409 reflections
b = 23.650 (2) Å	θ = 3.6–70.6°
c = 10.287 (2) Å	µ = 0.79 mm⁻¹
β = 91.841 (14)°	T = 293 K
V = 1341.8 (3) Å³	Prism, colourless
Z = 4	0.70 × 0.45 × 0.10 mm

Data collection top

Oxford Diffraction Xcalibur Ruby diffractometer	2460 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1877 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 10.2576 pixels mm^-1	θ_max = 70.8°, θ_min = 3.7°
ω scans	h = −6→5
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −22→28
T_min = 0.674, T_max = 1.000	l = −12→7
4791 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.0774P)² + 0.039P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.009
2460 reflections	Δρ_max = 0.18 e Å⁻³
191 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0116 (12)

Crystal data top

C₁₅H₁₂N₄O₂	V = 1341.8 (3) Å³
M_r = 280.29	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 5.5178 (5) Å	µ = 0.79 mm⁻¹
b = 23.650 (2) Å	T = 293 K
c = 10.287 (2) Å	0.70 × 0.45 × 0.10 mm
β = 91.841 (14)°

Data collection top

Oxford Diffraction Xcalibur Ruby diffractometer	2460 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1877 reflections with I > 2σ(I)
T_min = 0.674, T_max = 1.000	R_int = 0.026
4791 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.04	Δρ_max = 0.18 e Å⁻³
2460 reflections	Δρ_min = −0.13 e Å⁻³
191 parameters

Special details top

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.40 (release 27-04-2009 CrysAlis171 .NET) (compiled Apr 27 2009,10:20:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
O1	1.0509 (3)	0.12524 (6)	0.39435 (11)	0.0714 (4)
O2	0.8540 (2)	0.11948 (5)	0.58047 (11)	0.0523 (3)
N1	1.4934 (3)	0.25199 (7)	0.54437 (16)	0.0742 (5)
N2	0.3515 (3)	0.05484 (6)	0.64902 (15)	0.0623 (4)
N3	0.2755 (2)	0.02085 (7)	0.73956 (15)	0.0594 (4)
N4	0.4631 (2)	−0.01361 (5)	0.77328 (12)	0.0462 (3)
C1	1.3474 (4)	0.21113 (8)	0.49855 (17)	0.0633 (5)
H1	1.3699	0.1984	0.4143	0.076*
C2	1.4557 (4)	0.26924 (9)	0.66483 (19)	0.0704 (5)
H2	1.5531	0.2981	0.6987	0.084*
C3	1.2820 (4)	0.24710 (8)	0.74223 (17)	0.0666 (5)
H3	1.2648	0.2603	0.8265	0.080*
C4	1.1335 (3)	0.20495 (8)	0.69328 (16)	0.0582 (5)
H4	1.0141	0.1892	0.7437	0.070*
C5	1.1658 (3)	0.18666 (7)	0.56780 (15)	0.0485 (4)
C6	1.0211 (3)	0.14094 (7)	0.50420 (15)	0.0503 (4)
C7	0.7195 (3)	0.07246 (8)	0.52359 (16)	0.0600 (5)
H7A	0.8304	0.0464	0.4836	0.072*
H7B	0.6066	0.0863	0.4567	0.072*
C8	0.5854 (3)	0.04295 (7)	0.62530 (15)	0.0505 (4)
C9	0.6565 (3)	−0.00074 (7)	0.70339 (15)	0.0498 (4)
H9	0.8078	−0.0181	0.7075	0.060*
C10	0.4351 (3)	−0.05578 (7)	0.87124 (15)	0.0462 (4)
C11	0.2462 (3)	−0.05189 (8)	0.95377 (18)	0.0613 (5)
H11	0.1349	−0.0225	0.9442	0.074*
C12	0.2202 (3)	−0.09122 (9)	1.05070 (19)	0.0679 (5)
H12	0.0903	−0.0888	1.1059	0.082*
C13	0.3853 (4)	−0.13394 (9)	1.0659 (2)	0.0698 (5)
H13	0.3697	−0.1603	1.1323	0.084*
C14	0.5740 (4)	−0.13789 (10)	0.9831 (2)	0.0789 (6)
H14	0.6860	−0.1671	0.9934	0.095*
C15	0.5996 (3)	−0.09893 (9)	0.88416 (19)	0.0671 (5)
H15	0.7266	−0.1020	0.8273	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0949 (10)	0.0714 (9)	0.0485 (7)	−0.0203 (7)	0.0127 (6)	−0.0026 (6)
O2	0.0533 (6)	0.0509 (7)	0.0531 (6)	−0.0076 (5)	0.0077 (5)	−0.0050 (5)
N1	0.0808 (11)	0.0768 (11)	0.0660 (10)	−0.0296 (9)	0.0194 (8)	−0.0046 (8)
N2	0.0544 (8)	0.0561 (9)	0.0766 (10)	0.0028 (7)	0.0042 (7)	0.0052 (8)
N3	0.0433 (7)	0.0591 (9)	0.0761 (10)	0.0071 (7)	0.0071 (7)	0.0038 (8)
N4	0.0375 (6)	0.0472 (7)	0.0540 (7)	0.0014 (6)	0.0038 (5)	−0.0059 (6)
C1	0.0727 (11)	0.0645 (11)	0.0532 (10)	−0.0148 (10)	0.0140 (9)	−0.0010 (8)
C2	0.0777 (13)	0.0669 (12)	0.0670 (11)	−0.0241 (10)	0.0087 (10)	−0.0064 (10)
C3	0.0748 (12)	0.0681 (12)	0.0577 (11)	−0.0128 (10)	0.0123 (9)	−0.0138 (9)
C4	0.0587 (10)	0.0604 (11)	0.0565 (10)	−0.0068 (8)	0.0168 (8)	−0.0006 (8)
C5	0.0505 (8)	0.0460 (9)	0.0493 (8)	0.0009 (7)	0.0054 (7)	0.0033 (7)
C6	0.0565 (9)	0.0480 (9)	0.0465 (9)	0.0006 (8)	0.0057 (7)	0.0053 (7)
C7	0.0680 (11)	0.0559 (10)	0.0562 (10)	−0.0140 (9)	0.0022 (8)	−0.0067 (8)
C8	0.0489 (8)	0.0488 (9)	0.0538 (9)	−0.0055 (7)	0.0013 (7)	−0.0095 (7)
C9	0.0386 (7)	0.0567 (10)	0.0543 (9)	0.0003 (7)	0.0054 (7)	−0.0045 (8)
C10	0.0418 (7)	0.0460 (8)	0.0511 (8)	−0.0025 (7)	0.0053 (6)	−0.0076 (7)
C11	0.0521 (9)	0.0629 (11)	0.0699 (11)	0.0067 (8)	0.0157 (8)	−0.0027 (9)
C12	0.0606 (10)	0.0772 (13)	0.0673 (12)	−0.0039 (10)	0.0221 (9)	−0.0022 (10)
C13	0.0723 (12)	0.0686 (13)	0.0693 (12)	−0.0005 (10)	0.0130 (10)	0.0088 (10)
C14	0.0784 (13)	0.0700 (13)	0.0899 (15)	0.0212 (11)	0.0255 (11)	0.0180 (11)
C15	0.0612 (10)	0.0679 (12)	0.0738 (12)	0.0135 (10)	0.0261 (9)	0.0072 (10)

Geometric parameters (Å, º) top

O1—C6	1.2059 (19)	C5—C6	1.484 (2)
O2—C6	1.3301 (19)	C7—C8	1.476 (2)
O2—C7	1.450 (2)	C7—H7A	0.9700
N1—C2	1.327 (2)	C7—H7B	0.9700
N1—C1	1.334 (2)	C8—C9	1.359 (2)
N2—N3	1.309 (2)	C9—H9	0.9300
N2—C8	1.351 (2)	C10—C11	1.369 (2)
N3—N4	1.3536 (18)	C10—C15	1.369 (2)
N4—C9	1.3409 (19)	C11—C12	1.375 (3)
N4—C10	1.430 (2)	C11—H11	0.9300
C1—C5	1.376 (2)	C12—C13	1.366 (3)
C1—H1	0.9300	C12—H12	0.9300
C2—C3	1.369 (3)	C13—C14	1.369 (3)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.375 (2)	C14—C15	1.383 (3)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.378 (2)	C15—H15	0.9300
C4—H4	0.9300

C6—O2—C7	114.22 (13)	O2—C7—H7B	109.7
C2—N1—C1	116.19 (16)	C8—C7—H7B	109.7
N3—N2—C8	109.28 (14)	H7A—C7—H7B	108.2
N2—N3—N4	107.01 (13)	N2—C8—C9	108.11 (15)
C9—N4—N3	109.94 (14)	N2—C8—C7	122.22 (16)
C9—N4—C10	129.94 (13)	C9—C8—C7	129.55 (16)
N3—N4—C10	120.13 (13)	N4—C9—C8	105.66 (14)
N1—C1—C5	124.29 (17)	N4—C9—H9	127.2
N1—C1—H1	117.9	C8—C9—H9	127.2
C5—C1—H1	117.9	C11—C10—C15	120.38 (17)
N1—C2—C3	123.98 (18)	C11—C10—N4	119.46 (15)
N1—C2—H2	118.0	C15—C10—N4	120.15 (15)
C3—C2—H2	118.0	C10—C11—C12	120.25 (17)
C2—C3—C4	118.94 (17)	C10—C11—H11	119.9
C2—C3—H3	120.5	C12—C11—H11	119.9
C4—C3—H3	120.5	C13—C12—C11	119.91 (18)
C3—C4—C5	118.49 (16)	C13—C12—H12	120.0
C3—C4—H4	120.8	C11—C12—H12	120.0
C5—C4—H4	120.8	C12—C13—C14	119.8 (2)
C1—C5—C4	118.09 (16)	C12—C13—H13	120.1
C1—C5—C6	117.97 (15)	C14—C13—H13	120.1
C4—C5—C6	123.91 (15)	C13—C14—C15	120.7 (2)
O1—C6—O2	123.60 (16)	C13—C14—H14	119.7
O1—C6—C5	123.36 (16)	C15—C14—H14	119.7
O2—C6—C5	113.04 (14)	C10—C15—C14	119.00 (17)
O2—C7—C8	109.78 (13)	C10—C15—H15	120.5
O2—C7—H7A	109.7	C14—C15—H15	120.5
C8—C7—H7A	109.7

C8—N2—N3—N4	−0.57 (18)	N3—N2—C8—C7	177.18 (14)
N2—N3—N4—C9	0.18 (18)	O2—C7—C8—N2	94.82 (18)
N2—N3—N4—C10	179.94 (13)	O2—C7—C8—C9	−89.6 (2)
C2—N1—C1—C5	−0.2 (3)	N3—N4—C9—C8	0.28 (18)
C1—N1—C2—C3	1.1 (3)	C10—N4—C9—C8	−179.45 (15)
N1—C2—C3—C4	−1.0 (3)	N2—C8—C9—N4	−0.62 (17)
C2—C3—C4—C5	0.0 (3)	C7—C8—C9—N4	−176.70 (15)
N1—C1—C5—C4	−0.8 (3)	C9—N4—C10—C11	162.57 (16)
N1—C1—C5—C6	−178.98 (18)	N3—N4—C10—C11	−17.1 (2)
C3—C4—C5—C1	0.8 (3)	C9—N4—C10—C15	−15.9 (3)
C3—C4—C5—C6	178.92 (16)	N3—N4—C10—C15	164.39 (16)
C7—O2—C6—O1	4.0 (2)	C15—C10—C11—C12	0.2 (3)
C7—O2—C6—C5	−176.54 (14)	N4—C10—C11—C12	−178.28 (16)
C1—C5—C6—O1	−1.8 (3)	C10—C11—C12—C13	0.9 (3)
C4—C5—C6—O1	−179.94 (17)	C11—C12—C13—C14	−1.0 (3)
C1—C5—C6—O2	178.69 (15)	C12—C13—C14—C15	0.2 (3)
C4—C5—C6—O2	0.6 (2)	C11—C10—C15—C14	−1.1 (3)
C6—O2—C7—C8	165.90 (14)	N4—C10—C15—C14	177.40 (17)
N3—N2—C8—C9	0.76 (18)	C13—C14—C15—C10	0.9 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the triazole ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···N1ⁱ	0.93	2.64	3.550 (3)	165
C2—H2···O1ⁱⁱ	0.93	2.71	3.464 (2)	139
C15—H15···O1ⁱⁱⁱ	0.93	2.68	3.559 (2)	158
C7—H7a···Cg1^iv	0.97	2.92	3.313 (2)	106

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂N₄O₂
M_r	280.29
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	5.5178 (5), 23.650 (2), 10.287 (2)
β (°)	91.841 (14)
V (Å³)	1341.8 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.79
Crystal size (mm)	0.70 × 0.45 × 0.10

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.674, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4791, 2460, 1877
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.613

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.124, 1.04
No. of reflections	2460
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.13

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the triazole ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···N1ⁱ	0.93	2.644	3.550 (3)	165
C2—H2···O1ⁱⁱ	0.93	2.709	3.464 (2)	139
C15—H15···O1ⁱⁱⁱ	0.93	2.681	3.559 (2)	158
C7—H7a···Cg1^iv	0.97	2.917	3.313 (2)	106

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

Acknowledgements

Tashkent Institute of Irrigation and Melioration is thanked for support.

References

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Volume 66| Part 7| July 2010| Page o1674

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