3-Ethyl-4-phenyl-5-(2-pyrid­yl)-1,2,4-triazole

In the crystal structure of the title compound, C₁₅H₁₄N₄, all three aromatic rings, viz. 1,2,4-triazole, pyridine and benzene. The crystal structure shows that all three rings are not coplanar.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.057
• wR factor = 0.122
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT301_ALERT_3_C Main Residue  Disorder .........................      10.00 Perc.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      17.40 Deg.
              C14  -C2   -C14'    1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

3-Ethyl-4-phenyl-5-(2-pyridyl)-1,2,4-triazole

Crystal data

C15H14N4	F(000) = 528
Mr = 250.30	Dx = 1.241 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1381 reflections
a = 10.4365 (14) Å	θ = 2.3–20.0°
b = 9.0713 (12) Å	µ = 0.08 mm^−1
c = 14.1861 (18) Å	T = 273 K
β = 94.107 (3)°	Rhombohedra, colorless
V = 1339.6 (3) Å^3	0.30 × 0.24 × 0.22 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2625 independent reflections
Radiation source: sealed tube	1547 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→12
Tmin = 0.98, Tmax = 0.98	k = −11→11
7002 measured reflections	l = −17→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.05P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2625 reflections	Δρmax = 0.13 e Å^−3
194 parameters	Δρmin = −0.12 e Å^−3
4 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0071 (18)

Special details

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

7.9512 (0.0067) x + 3.9089 (0.0084) y + 6.0689 (0.0126) z = 1.8505 (0.0042)

* -0.0162 (0.0017) C3 * 0.0077 (0.0017) C4 * 0.0122 (0.0017) C5 * -0.0226 (0.0017) C6 * 0.0139 (0.0016) C7 * 0.0049 (0.0016) N4

Rms deviation of fitted atoms = 0.0142

8.1861 (0.0076) x + 4.8700 (0.0088) y + 3.5996 (0.0149) z = 1.7476 (0.0010)

Angle to previous plane (with approximate e.s.d.) = 11.71 (0.15)

* 0.0041 (0.0014) C1 * -0.0025 (0.0012) N2 * -0.0002 (0.0013) N3 * 0.0026 (0.0014) C2 * -0.0040 (0.0014) N1

Rms deviation of fitted atoms = 0.0030

- 7.2037 (0.0077) x + 5.9165 (0.0069) y + 5.1348 (0.0121) z = 0.3158 (0.0042)

Angle to previous plane (with approximate e.s.d.) = 84.61 (0.07)

* 0.0089 (0.0017) C8 * -0.0035 (0.0017) C9 * -0.0045 (0.0017) C10 * 0.0073 (0.0016) C11 * -0.0021 (0.0016) C12 * -0.0061 (0.0018) C13

Rms deviation of fitted atoms = 0.0059

7.9512 (0.0067) x + 3.9089 (0.0084) y + 6.0689 (0.0126) z = 1.8505 (0.0042)

Angle to previous plane (with approximate e.s.d.) = 84.65 (0.06)

* -0.0162 (0.0017) C3 * 0.0077 (0.0017) C4 * 0.0122 (0.0017) C5 * -0.0226 (0.0017) C6 * 0.0139 (0.0016) C7 * 0.0049 (0.0016) N4

Rms deviation of fitted atoms = 0.0142

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.0511 (2)	0.2001 (2)	0.09967 (16)	0.0587 (6)
C2	0.1736 (2)	0.0260 (2)	0.05616 (16)	0.0580 (6)
C3	−0.0306 (2)	0.2937 (3)	0.15315 (16)	0.0606 (6)
C4	−0.0683 (2)	0.2499 (2)	0.23468 (15)	0.0526 (6)
H4	−0.0418	0.1596	0.2603	0.063*
C5	−0.1455 (2)	0.3378 (3)	0.27995 (16)	0.0574 (6)
H5	−0.1712	0.3070	0.3382	0.069*
C6	−0.1882 (2)	0.4681 (3)	0.24629 (16)	0.0625 (6)
H6	−0.2461	0.5230	0.2788	0.075*
C7	−0.1460 (2)	0.5184 (2)	0.16463 (16)	0.0604 (6)
H7	−0.1705	0.6112	0.1421	0.072*
C8	0.1152 (2)	0.0034 (3)	0.22098 (17)	0.0600 (6)
C9	0.0311 (2)	−0.1115 (2)	0.23292 (16)	0.0601 (6)
H9	−0.0270	−0.1408	0.1837	0.072*
C10	0.0349 (2)	−0.1818 (2)	0.31900 (15)	0.0585 (6)
H10	−0.0211	−0.2594	0.3283	0.070*
C11	0.1217 (2)	−0.1373 (2)	0.39179 (16)	0.0555 (6)
H11	0.1229	−0.1840	0.4502	0.067*
C12	0.2060 (2)	−0.0243 (2)	0.37809 (16)	0.0591 (6)
H12	0.2650	0.0047	0.4268	0.071*
C13	0.2026 (2)	0.0461 (2)	0.29144 (16)	0.0609 (6)
H13	0.2598	0.1223	0.2814	0.073*
C14	0.2595 (6)	−0.1060 (6)	0.0682 (4)	0.0477 (19)	0.527 (5)
H14A	0.2065	−0.1895	0.0832	0.057*	0.527 (5)
H14B	0.3188	−0.0886	0.1229	0.057*	0.527 (5)
C15	0.3372 (5)	−0.1506 (5)	−0.0121 (3)	0.0674 (16)	0.527 (5)
H15A	0.2814	−0.1623	−0.0684	0.101*	0.527 (5)
H15B	0.3801	−0.2421	0.0029	0.101*	0.527 (5)
H15C	0.3998	−0.0757	−0.0222	0.101*	0.527 (5)
C14'	0.2349 (6)	−0.1211 (5)	0.0424 (6)	0.058 (3)	0.473 (5)
H14C	0.2288	−0.1501	−0.0236	0.070*	0.473 (5)
H14D	0.1972	−0.1971	0.0797	0.070*	0.473 (5)
C15'	0.3711 (6)	−0.0892 (6)	0.0775 (4)	0.075 (2)	0.473 (5)
H15D	0.4023	−0.0061	0.0439	0.112*	0.473 (5)
H15E	0.4237	−0.1737	0.0671	0.112*	0.473 (5)
H15F	0.3746	−0.0673	0.1438	0.112*	0.473 (5)
N1	0.1111 (2)	0.0747 (2)	0.13074 (13)	0.0615 (5)
N2	0.07398 (18)	0.2253 (2)	0.01175 (13)	0.0559 (5)
N3	0.15335 (18)	0.1119 (2)	−0.01468 (13)	0.0574 (5)
N4	−0.06543 (18)	0.43030 (19)	0.11431 (12)	0.0566 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0571 (15)	0.0573 (14)	0.0622 (14)	−0.0145 (12)	0.0071 (12)	0.0072 (12)
C2	0.0594 (14)	0.0620 (14)	0.0551 (13)	−0.0096 (12)	0.0217 (11)	0.0017 (12)
C3	0.0569 (15)	0.0646 (15)	0.0593 (13)	−0.0040 (12)	−0.0036 (11)	0.0075 (12)
C4	0.0562 (13)	0.0475 (11)	0.0586 (12)	0.0112 (10)	0.0357 (11)	0.0131 (10)
C5	0.0561 (14)	0.0592 (14)	0.0601 (14)	−0.0075 (11)	0.0258 (12)	0.0092 (11)
C6	0.0658 (16)	0.0613 (14)	0.0632 (15)	0.0072 (12)	0.0241 (12)	−0.0137 (12)
C7	0.0666 (15)	0.0516 (12)	0.0649 (14)	0.0180 (12)	0.0177 (12)	0.0186 (11)
C8	0.0576 (14)	0.0613 (14)	0.0626 (14)	0.0066 (12)	0.0143 (11)	0.0011 (11)
C9	0.0634 (15)	0.0605 (13)	0.0571 (14)	−0.0072 (12)	0.0086 (11)	0.0173 (11)
C10	0.0650 (15)	0.0513 (12)	0.0593 (13)	−0.0165 (11)	0.0061 (12)	0.0131 (11)
C11	0.0565 (14)	0.0583 (14)	0.0531 (13)	0.0098 (11)	0.0144 (11)	0.0230 (11)
C12	0.0541 (14)	0.0557 (13)	0.0653 (14)	0.0028 (10)	−0.0108 (11)	0.0076 (11)
C13	0.0674 (16)	0.0554 (13)	0.0603 (14)	−0.0128 (11)	0.0062 (12)	0.0134 (11)
C14	0.047 (4)	0.052 (3)	0.046 (3)	0.013 (3)	0.014 (3)	−0.009 (2)
C15	0.059 (3)	0.080 (3)	0.063 (3)	0.014 (2)	0.007 (2)	−0.016 (2)
C14'	0.063 (5)	0.053 (4)	0.059 (4)	−0.018 (3)	0.010 (4)	−0.006 (3)
C15'	0.076 (5)	0.063 (3)	0.086 (4)	0.021 (3)	0.008 (3)	0.011 (3)
N1	0.0614 (13)	0.0643 (13)	0.0613 (12)	−0.0050 (9)	0.0214 (10)	0.0010 (9)
N2	0.0566 (12)	0.0543 (10)	0.0588 (10)	−0.0161 (9)	0.0166 (9)	0.0077 (9)
N3	0.0547 (12)	0.0565 (11)	0.0637 (12)	−0.0236 (9)	0.0235 (9)	0.0001 (10)
N4	0.0504 (11)	0.0602 (11)	0.0597 (12)	0.0200 (9)	0.0076 (9)	0.0269 (9)

Geometric parameters (Å, º)

C1—N2	1.307 (3)	C9—H9	0.9300
C1—N1	1.357 (3)	C10—C11	1.384 (3)
C1—C3	1.454 (3)	C10—H10	0.9300
C2—N3	1.277 (3)	C11—C12	1.374 (3)
C2—N1	1.356 (3)	C11—H11	0.9300
C2—C14	1.499 (2)	C12—C13	1.383 (3)
C2—C14'	1.499 (2)	C12—H12	0.9300
C3—C4	1.310 (3)	C13—H13	0.9300
C3—N4	1.394 (3)	C14—C15	1.500 (2)
C4—C5	1.331 (3)	C14—H14A	0.9700
C4—H4	0.9300	C14—H14B	0.9700
C5—C6	1.339 (3)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—C7	1.348 (3)	C15—H15C	0.9600
C6—H6	0.9300	C14'—C15'	1.500 (2)
C7—N4	1.394 (3)	C14'—H14C	0.9700
C7—H7	0.9300	C14'—H14D	0.9700
C8—C13	1.361 (3)	C15'—H15D	0.9600
C8—C9	1.381 (3)	C15'—H15E	0.9600
C8—N1	1.432 (3)	C15'—H15F	0.9600
C9—C10	1.376 (3)	N2—N3	1.389 (3)
N2—C1—N1	110.2 (2)	C12—C11—C10	120.3 (2)
N2—C1—C3	123.4 (2)	C12—C11—H11	119.9
N1—C1—C3	126.4 (2)	C10—C11—H11	119.9
N3—C2—N1	110.69 (19)	C11—C12—C13	119.6 (2)
N3—C2—C14	129.9 (3)	C11—C12—H12	120.2
N1—C2—C14	119.2 (3)	C13—C12—H12	120.2
N3—C2—C14'	119.3 (4)	C8—C13—C12	119.6 (2)
N1—C2—C14'	128.7 (4)	C8—C13—H13	120.2
C14—C2—C14'	17.4 (4)	C12—C13—H13	120.2
C4—C3—N4	122.2 (2)	C2—C14—C15	118.7 (4)
C4—C3—C1	120.5 (2)	C2—C14—H14A	107.6
N4—C3—C1	117.3 (2)	C15—C14—H14A	107.6
C3—C4—C5	118.3 (2)	C2—C14—H14B	107.6
C3—C4—H4	120.8	C15—C14—H14B	107.6
C5—C4—H4	120.8	H14A—C14—H14B	107.1
C4—C5—C6	123.7 (2)	C2—C14'—C15'	100.8 (4)
C4—C5—H5	118.2	C2—C14'—H14C	111.6
C6—C5—H5	118.2	C15'—C14'—H14C	111.6
C5—C6—C7	119.0 (2)	C2—C14'—H14D	111.6
C5—C6—H6	120.5	C15'—C14'—H14D	111.6
C7—C6—H6	120.5	H14C—C14'—H14D	109.4
C6—C7—N4	119.46 (19)	C14'—C15'—H15D	109.5
C6—C7—H7	120.3	C14'—C15'—H15E	109.5
N4—C7—H7	120.3	H15D—C15'—H15E	109.5
C13—C8—C9	121.6 (2)	C14'—C15'—H15F	109.5
C13—C8—N1	120.3 (2)	H15D—C15'—H15F	109.5
C9—C8—N1	118.1 (2)	H15E—C15'—H15F	109.5
C10—C9—C8	118.7 (2)	C2—N1—C1	104.85 (19)
C10—C9—H9	120.6	C2—N1—C8	124.4 (2)
C8—C9—H9	120.6	C1—N1—C8	130.7 (2)
C9—C10—C11	120.1 (2)	C1—N2—N3	106.35 (19)
C9—C10—H10	119.9	C2—N3—N2	107.93 (17)
C11—C10—H10	119.9	C7—N4—C3	117.23 (18)