J Chem Crystallogr (2009) 39:32–35
33
2.479(s, 3H, CH3–), 7.175–7.211(d, 1H, J = 8 Hz, Ar–H),
7.553–7.726(m, 4H, Ar–H); 8.022–8.059(d, 1H, J = 8 Hz,
Ar–H), 8.131–8.171(d, 1H, J = 8 Hz, Ar–H), 12.80–13.25
Table 1 Crystal data and summary of data collection and structure
refinement
Compound No
Compound
4a
4b
þ
ꢀ
(b, 1H, –COOH)ppm. MS M/z(%): 253 (M , 9%), 236(1),
C9H8BrN3
288845
C13H11N3
233391
224(2), 209(4), 196(1), 181(45), 180(100), 178(20), 168(5),
153(18), 140(9), 127(80), 115(6), 101(16), 83(36), 77(38),
75(22), 63(17).
CCDC deposit No
Color
Colorless/block
238.09
Light yellow/block
209.25
Formula weight
Temperature,°C
Crystal system
Space group
20(293 K)
Monoclinic
P2(1)/n
20(293 K)
Orthorhombic
Pbca(P212121)
General Procedure of Preparation of 1-Aryl-5-methyl-
1,2,3-triazole Derivatives 4a–b
˚
Unit-cell dimensions a = 11.660(2) A
˚
a = 10.373(2) A
˚
b = 7.668(2) A
˚
b = 11.691(2) A
A mixture of 1 mmol 1-aryl-5-methyl-1,2,3-triazol-4-car-
boxylic acids 3a–b and 1 mmol amino group derivatives
was heated to melt point temperature in a 100 mL round
bottomed for 3–16 h. After the reaction mixture was
cooled, some ice was added, the solution was neutralized to
pH = 7 with the solution of sodium hydroxide and the
solid residue was separated by column chromatography
(CH3CO2CH2CH3: petroleum ether = 1:5) to afford 4a–b.
4a, 1-(4-Bromophenyl)-5-methyl-1,2,3-triazole, m.p.
98–99 °C(98.5–99.5 Literature [10], 164 Literature [12])
(47.5%), 1H NMR(200 MHz, CDCl3) dH: 2.366(s, 3H,
CH3–), 7.350–7.393(d, 2H, J = 8.6 Hz, Ar–H), 7.608(s,
1H), 7.668–7.711(d, 2H, J = 8.6 Hz, Ar–H) ppm.
˚
c = 11.818(2) A
˚
c = 17.579(4) A
a = 90.00°
b = 116.01(3)°
c = 90.008
a = 90.008
b = 90.008
c = 90.008
2131.8(7)
8
3
Volume (A )
˚
949.6(3)
4
Z
D
calc, g cm-3
1.665
1.304
F(000)
472
880
Index ranges
0 B h B 13;
0 B k B 9;
-14 B l B 12
4.283
0 B h B 12
0 B k B 13
0 B l B 20
0.081
Absorption
coefficient, mm-1
4b, 5-Methyl-1-(1-naphthyl)-1,2,3-triazole is a light
yellow crystalline solid, m.p. 117–118 °C[Lit. 125–127 °C
Diffractometer/Scan
Enraf-Nonius
CAD4, x/2h
Enraf-Nonius
CAD4, x/2h
1
[12]], (72%). H NMR(200 MHz, CDCl3)dH: 2.479(s, 3H,
˚
˚
Radiation/k
Moka/0.71073 A
Moka/ 0.71073 A
CH3–), 7.175–7.211(d, 1H, J = 7.2 Hz, Ar–H), 7.553–
7.726(m, 4H, Ar–H), 7.589(s, 1H), 8.022–8.059(d, 1H,
J = 7.4 Hz, Ar–H), 8.131–8.171(d, 1H, J = 8 Hz,
Ar–H)ppm.
hmin, hmax, (°)
Reflections measured 1,458
0.874–24.99
0.983–24.94
2,105
Independent/observed 755
reflections
1,307
The purified product was dissolved in ethyl acetate,
petroleum ether. The crystal was obtained after 10d by
evaporation of the solvent.
Data/restraints/
parameters
1458/0/119
2105/0/290
Refinement method
Full-matrix least-
squares on F2
Full-matrix least-
squares on F2
Goodness-of-fit on F2 1.051
1.005
0.089
Crystal Structure Determinations and Refinement
Shift/su_max
0.167
Single crystals were selected and mounted on the tip of a
glass fiber. Preliminary examination and data collection
Final R indices
R1 = 0.0477,
wR2 = 0.0997
R1 = 0.0565,
wR2 = 0.1374
˚
R indices [I [ 2r(I)] R1 = 0.1450,
wR2 = 0.1127
R1 = 0.1105,
wR2 = 0.1562
were performed with MoJa radiation (k = 0.71073 A) on
an Enraf-Nonius CAD4 computer controlled kappa axis
diffractometer operating in the x/2h scanning mode. The
structure was determined by direct methods (SHELXS-97)
and refined by full covariance matrix methods (SHELXL-
97). The crystal data, data collection and the refinement
parameter for the structure are given in Table 1.
Largest diff. Peak
and hole
0.251 and
-0.213 e A
0.197 and
-0.202 e A
-3
-3
˚
˚
Results and Discussion
The structure of the title compound 4a is shown in
Fig. 1. Selected bond lengths and angles are given in
Table 2. The structure of the title compound 4b is shown
in Fig. 2. Selected bond lengths and angles are given in
Table 3. The geometric calculations were performed using
the program SHELX-97.
The structure of these compounds was characterized with
1H NMR, IR and MS spectroscopy and results are given.
The IR spectra data of compound 3a–b characteristic peaks
at 3,429–3,444 and 1,690–1,725 cm-1 could be found.
These peaks could be assigned to COOH and mC=O
The vibration bands of N–N=N were in the region
.
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