(1-Phenyl-1H-1,2,3-triazol-4-yl)methyl pyridine-3-carboxyl-ate.

In the title compound, C(15)H(12)N(4)O(2), the dihedral angle between the planes of the nicotino-yloxy 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 inter-molecular C-H⋯N, C-H⋯O and C-H⋯π(triazole) hydrogen bonds and aromatic π-π stacking inter-actions 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 = 280.29

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.124

S = 1.04

2460 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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.

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

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

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

C15H12N4O2	F(000) = 584
Mr = 280.29	Dx = 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

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

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(Fo2) + (0.0774P)2 + 0.039P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.009
2460 reflections	Δρmax = 0.18 e Å−3
191 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···Cg1iv	0.97	2.917	3.313 (2)	106

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⋯Cg1iv	0.97	2.92	3.313 (2)	106

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .