Methyl 1-benzyl-1H-1,2,3-triazole-4-carboxyl-ate.

In the title compound, C(11)H(11)N(3)O(2), prepared by the [3+2] cycloaddition reaction of benzyl azide with methyl propiolate, the dihedral angle between the ring planes is 67.87 (11)°.

Related literature

For catalytic transformations of organic alkynes mediated by ruthenium complexes, see: Naota et al. (1998 ▶); Bruneau & Dixneuf (1999 ▶); Trost et al. (2001 ▶); Chen et al. (2009 ▶); Cheng et al. (2009 ▶). For the synthesis of triazoles, see: Padwa (1976 ▶). For applications of triazoles, see: Krivopalov & Shkurko (2005 ▶).

Experimental

Crystal data

C11H11N3O2

M = 217.23

Monoclinic,

a = 12.0551 (6) Å

b = 5.6285 (3) Å

c = 16.7578 (10) Å

β = 110.664 (3)°

V = 1063.90 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.55 × 0.40 × 0.35 mm

Data collection

Nonuis KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.949, T max = 0.967

7021 measured reflections

1845 independent reflections

1615 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.091

S = 1.01

1845 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022531/bh2294sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022531/bh2294Isup2.hkl

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

C11H11N3O2	F(000) = 456
Mr = 217.23	Dx = 1.356 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3680 reflections
a = 12.0551 (6) Å	θ = 2.6–25.0°
b = 5.6285 (3) Å	µ = 0.10 mm−1
c = 16.7578 (10) Å	T = 200 K
β = 110.664 (3)°	Prism, colorless
V = 1063.90 (10) Å3	0.55 × 0.40 × 0.35 mm
Z = 4

Nonuis KappaCCD diffractometer	1845 independent reflections
Radiation source: fine-focus sealed tube	1615 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 9 pixels mm-1	θmax = 25.0°, θmin = 1.8°
CCD rotation images, thick slices scans	h = −14→14
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −6→6
Tmin = 0.949, Tmax = 0.967	l = −19→18
7021 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0442P)2 + 0.2782P] where P = (Fo2 + 2Fc2)/3
1845 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.16 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
C1	−0.11251 (12)	1.1370 (3)	0.66802 (10)	0.0462 (4)
H1A	−0.1102	1.3069	0.6814	0.069*
H1B	−0.1054	1.0444	0.7191	0.069*
H1C	−0.1878	1.0991	0.6226	0.069*
C2	−0.00887 (11)	0.8505 (2)	0.61959 (8)	0.0359 (3)
C3	0.09145 (10)	0.8061 (2)	0.59130 (8)	0.0344 (3)
C4	0.13667 (11)	0.5915 (2)	0.57855 (8)	0.0379 (3)
H4	0.1102	0.4373	0.5864	0.045*
C5	0.30857 (12)	0.4920 (2)	0.53001 (10)	0.0441 (3)
H5A	0.3067	0.5334	0.4721	0.053*
H5B	0.2820	0.3252	0.5288	0.053*
C6	0.43422 (11)	0.5135 (2)	0.59233 (8)	0.0359 (3)
C7	0.48209 (14)	0.3404 (3)	0.65326 (10)	0.0508 (4)
H7	0.4357	0.2066	0.6564	0.061*
C8	0.59814 (16)	0.3616 (4)	0.71015 (11)	0.0662 (5)
H8	0.6306	0.2417	0.7518	0.079*
C9	0.66570 (14)	0.5532 (4)	0.70663 (11)	0.0647 (5)
H9	0.7448	0.5669	0.7456	0.078*
C10	0.61865 (14)	0.7251 (3)	0.64659 (12)	0.0630 (5)
H10	0.6653	0.8590	0.6442	0.076*
C11	0.50372 (12)	0.7062 (3)	0.58917 (10)	0.0488 (4)
H11	0.4724	0.8262	0.5474	0.059*
N1	0.15518 (9)	0.98335 (18)	0.57253 (7)	0.0379 (3)
N2	0.23722 (9)	0.88701 (19)	0.54855 (8)	0.0404 (3)
N3	0.22627 (9)	0.64798 (18)	0.55266 (7)	0.0380 (3)
O1	−0.01523 (8)	1.07905 (16)	0.63991 (6)	0.0417 (3)
O2	−0.07666 (8)	0.69845 (17)	0.62483 (7)	0.0480 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0442 (8)	0.0438 (8)	0.0558 (9)	−0.0033 (6)	0.0239 (7)	−0.0050 (6)
C2	0.0330 (6)	0.0314 (6)	0.0372 (7)	−0.0041 (5)	0.0047 (5)	0.0008 (5)
C3	0.0298 (6)	0.0293 (6)	0.0373 (7)	−0.0038 (5)	0.0032 (5)	−0.0005 (5)
C4	0.0326 (6)	0.0298 (6)	0.0456 (8)	−0.0047 (5)	0.0067 (6)	−0.0009 (5)
C5	0.0396 (7)	0.0351 (7)	0.0554 (8)	0.0013 (6)	0.0143 (6)	−0.0090 (6)
C6	0.0361 (7)	0.0332 (7)	0.0416 (7)	0.0016 (5)	0.0177 (6)	−0.0016 (5)
C7	0.0564 (9)	0.0444 (8)	0.0557 (9)	0.0048 (7)	0.0248 (7)	0.0087 (7)
C8	0.0688 (11)	0.0781 (13)	0.0459 (9)	0.0277 (10)	0.0131 (8)	0.0094 (8)
C9	0.0395 (8)	0.0891 (14)	0.0590 (10)	0.0112 (9)	0.0091 (7)	−0.0207 (10)
C10	0.0409 (8)	0.0662 (11)	0.0854 (13)	−0.0141 (8)	0.0266 (8)	−0.0157 (9)
C11	0.0439 (8)	0.0435 (8)	0.0618 (9)	−0.0029 (6)	0.0221 (7)	0.0054 (7)
N1	0.0323 (5)	0.0309 (6)	0.0472 (7)	−0.0012 (4)	0.0098 (5)	−0.0001 (5)
N2	0.0358 (6)	0.0300 (6)	0.0533 (7)	−0.0010 (4)	0.0134 (5)	−0.0008 (5)
N3	0.0329 (5)	0.0283 (5)	0.0474 (7)	−0.0015 (4)	0.0076 (5)	−0.0037 (5)
O1	0.0387 (5)	0.0336 (5)	0.0555 (6)	−0.0053 (4)	0.0199 (4)	−0.0067 (4)
O2	0.0437 (5)	0.0365 (5)	0.0641 (7)	−0.0083 (4)	0.0196 (5)	0.0017 (4)

C1—O1	1.4469 (16)	C5—H5B	0.9900
C1—H1A	0.9800	C6—C7	1.3817 (19)
C1—H1B	0.9800	C6—C11	1.3830 (19)
C1—H1C	0.9800	C7—C8	1.392 (2)
C2—O2	1.2076 (15)	C7—H7	0.9500
C2—O1	1.3400 (15)	C8—C9	1.365 (3)
C2—C3	1.4678 (19)	C8—H8	0.9500
C3—N1	1.3621 (16)	C9—C10	1.367 (3)
C3—C4	1.3722 (17)	C9—H9	0.9500
C4—N3	1.3367 (17)	C10—C11	1.384 (2)
C4—H4	0.9500	C10—H10	0.9500
C5—N3	1.4713 (17)	C11—H11	0.9500
C5—C6	1.5110 (18)	N1—N2	1.3092 (15)
C5—H5A	0.9900	N2—N3	1.3560 (15)
O1—C1—H1A	109.5	C11—C6—C5	120.62 (12)
O1—C1—H1B	109.5	C6—C7—C8	120.16 (15)
H1A—C1—H1B	109.5	C6—C7—H7	119.9
O1—C1—H1C	109.5	C8—C7—H7	119.9
H1A—C1—H1C	109.5	C9—C8—C7	120.57 (16)
H1B—C1—H1C	109.5	C9—C8—H8	119.7
O2—C2—O1	124.12 (13)	C7—C8—H8	119.7
O2—C2—C3	123.97 (12)	C8—C9—C10	119.48 (15)
O1—C2—C3	111.90 (10)	C8—C9—H9	120.3
N1—C3—C4	108.74 (11)	C10—C9—H9	120.3
N1—C3—C2	123.10 (11)	C9—C10—C11	120.74 (16)
C4—C3—C2	128.16 (11)	C9—C10—H10	119.6
N3—C4—C3	104.61 (11)	C11—C10—H10	119.6
N3—C4—H4	127.7	C6—C11—C10	120.32 (15)
C3—C4—H4	127.7	C6—C11—H11	119.8
N3—C5—C6	112.13 (11)	C10—C11—H11	119.8
N3—C5—H5A	109.2	N2—N1—C3	108.43 (10)
C6—C5—H5A	109.2	N1—N2—N3	107.32 (10)
N3—C5—H5B	109.2	C4—N3—N2	110.89 (11)
C6—C5—H5B	109.2	C4—N3—C5	129.62 (11)
H5A—C5—H5B	107.9	N2—N3—C5	119.49 (11)
C7—C6—C11	118.73 (13)	C2—O1—C1	115.14 (10)
C7—C6—C5	120.65 (12)