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The title compound, C
14H
12N
4, is a disubstituted 1,2,4-triazole derivative. The triazole ring is planar and its dihedral angles with the attached pyridyl and methylphenyl rings are 25.2 (3) and 66.9 (3)°, respectively. The crystal structure is stabilized by a number of C—H
N hydrogen bonds and C—H
π intermolecular interactions.
Supporting information
CCDC reference: 259120
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.056
- wR factor = 0.170
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT480_ALERT_4_B Long H...A H-Bond Reported H5F .. \P .. 3.02 Ang.
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 44 Perc.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. N1 .. 2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5F .. N1P .. 2.93 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3# .. N1P .. 2.87 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5P .. N1 .. 2.96 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5P .. N2 .. 2.96 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6P .. N1 .. 2.95 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6F .. N2 .. 2.98 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3F .. \P .. 2.94 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C3F .. \P .. 3.85 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C5F .. \P .. 3.82 Ang.
PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... CFF
H7F1 CFF H7F2
PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... \P
H3F \P
PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... \P
H5F \P
PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... \P
C3F \P
PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... \P
C5F \P
PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... \P
C3F H3F \P
PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... \P
C5F H5F \P
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
19 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
12 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: KM-4 Software (Kuma, 1998); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 and enCIFer (Allen et al., 2004).
4-(4-methylphenyl)-3-(4-pyridyl)-4
H-1,2,4-triazole
top
Crystal data top
C14H12N4 | F(000) = 496 |
Mr = 236.28 | Dx = 1.320 Mg m−3 |
Monoclinic, P21/c | Melting point: 447 K |
Hall symbol: -P 2ybc | Cu Kα radiation, λ = 1.54178 Å |
a = 7.741 (2) Å | Cell parameters from 56 reflections |
b = 7.053 (1) Å | θ = 6–18° |
c = 21.945 (4) Å | µ = 0.66 mm−1 |
β = 96.99 (3)° | T = 293 K |
V = 1189.2 (4) Å3 | Needle, orange |
Z = 4 | 0.51 × 0.10 × 0.07 mm |
Data collection top
Kuma KM4 four-circle diffractometer | Rint = 0.014 |
Radiation source: fine-focus sealed tube | θmax = 80.3°, θmin = 4.1° |
Graphite monochromator | h = −9→9 |
ω–2θ scan | k = 0→8 |
2531 measured reflections | l = 0→28 |
2485 independent reflections | 3 standard reflections every 100 reflections |
1105 reflections with I > 2σ(I) | intensity decay: 0.7% |
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)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.170 | w = 1/[σ2(Fo2) + (0.096P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
2485 reflections | Δρmax = 0.23 e Å−3 |
165 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0039 (8) |
Special details top
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 | Uiso*/Ueq | |
N1 | 0.8224 (3) | 0.6540 (4) | 0.75655 (11) | 0.0614 (7) | |
N2 | 0.6529 (3) | 0.7074 (4) | 0.73741 (11) | 0.0561 (6) | |
C3 | 0.5902 (3) | 0.5918 (4) | 0.69410 (13) | 0.0481 (7) | |
N4 | 0.7126 (3) | 0.4604 (3) | 0.68341 (10) | 0.0463 (5) | |
C5 | 0.8546 (4) | 0.5079 (5) | 0.72340 (14) | 0.0557 (7) | |
H5 | 0.9606 | 0.4444 | 0.7266 | 0.067* | |
N1p | 0.0671 (3) | 0.6464 (4) | 0.60818 (12) | 0.0631 (7) | |
C2p | 0.1500 (4) | 0.4809 (5) | 0.60976 (15) | 0.0609 (8) | |
H2p | 0.0901 | 0.3771 | 0.5917 | 0.073* | |
C3p | 0.3183 (4) | 0.4530 (4) | 0.63631 (13) | 0.0537 (7) | |
H3p | 0.3688 | 0.3333 | 0.6366 | 0.064* | |
C4p | 0.4107 (3) | 0.6050 (4) | 0.66251 (12) | 0.0465 (7) | |
C5p | 0.3272 (4) | 0.7784 (4) | 0.66162 (14) | 0.0555 (7) | |
H5p | 0.3848 | 0.8848 | 0.6789 | 0.067* | |
C6p | 0.1568 (4) | 0.7913 (5) | 0.63460 (14) | 0.0631 (8) | |
H6p | 0.1016 | 0.9083 | 0.6349 | 0.076* | |
C1f | 0.7117 (3) | 0.3182 (4) | 0.63634 (12) | 0.0467 (6) | |
C2f | 0.7022 (4) | 0.3715 (4) | 0.57596 (13) | 0.0536 (7) | |
H2f | 0.6882 | 0.4987 | 0.5652 | 0.064* | |
C3f | 0.7132 (4) | 0.2376 (4) | 0.53143 (14) | 0.0589 (8) | |
H3f | 0.7064 | 0.2752 | 0.4906 | 0.071* | |
C4f | 0.7345 (4) | 0.0466 (4) | 0.54605 (14) | 0.0531 (7) | |
C5f | 0.7401 (4) | −0.0030 (4) | 0.60691 (15) | 0.0565 (8) | |
H5f | 0.7519 | −0.1303 | 0.6178 | 0.068* | |
C6f | 0.7286 (4) | 0.1298 (4) | 0.65225 (14) | 0.0547 (7) | |
H6f | 0.7323 | 0.0927 | 0.6931 | 0.066* | |
C7f | 0.7554 (5) | −0.0992 (5) | 0.49775 (16) | 0.0744 (10) | |
H7f1 | 0.7558 | −0.0378 | 0.4587 | 0.089* | |
H7f2 | 0.6606 | −0.1876 | 0.4956 | 0.089* | |
H7f3 | 0.8633 | −0.1655 | 0.5081 | 0.089* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0561 (15) | 0.0670 (17) | 0.0594 (15) | −0.0016 (13) | −0.0001 (11) | −0.0080 (13) |
N2 | 0.0607 (14) | 0.0524 (14) | 0.0544 (14) | 0.0023 (12) | 0.0034 (11) | −0.0062 (12) |
C3 | 0.0496 (15) | 0.0458 (15) | 0.0499 (14) | 0.0017 (11) | 0.0107 (12) | −0.0019 (12) |
N4 | 0.0414 (11) | 0.0472 (12) | 0.0503 (12) | 0.0003 (10) | 0.0052 (9) | −0.0001 (11) |
C5 | 0.0478 (15) | 0.0628 (19) | 0.0557 (16) | −0.0015 (14) | 0.0028 (12) | 0.0000 (15) |
N1p | 0.0514 (14) | 0.0698 (17) | 0.0680 (17) | 0.0075 (14) | 0.0063 (12) | −0.0027 (14) |
C2p | 0.0489 (15) | 0.063 (2) | 0.0704 (19) | 0.0005 (14) | 0.0057 (14) | −0.0082 (16) |
C3p | 0.0499 (15) | 0.0489 (16) | 0.0625 (17) | 0.0024 (13) | 0.0081 (13) | −0.0024 (14) |
C4p | 0.0469 (15) | 0.0491 (16) | 0.0446 (14) | 0.0046 (11) | 0.0101 (11) | 0.0016 (12) |
C5p | 0.0590 (17) | 0.0473 (17) | 0.0600 (18) | 0.0092 (14) | 0.0066 (13) | −0.0052 (14) |
C6p | 0.0579 (18) | 0.0577 (19) | 0.075 (2) | 0.0156 (15) | 0.0121 (15) | −0.0005 (17) |
C1f | 0.0397 (14) | 0.0461 (17) | 0.0547 (16) | 0.0037 (11) | 0.0075 (11) | −0.0008 (13) |
C2f | 0.0645 (17) | 0.0403 (15) | 0.0566 (17) | 0.0007 (13) | 0.0096 (13) | 0.0059 (13) |
C3f | 0.0692 (19) | 0.0591 (19) | 0.0490 (17) | −0.0013 (15) | 0.0094 (13) | 0.0032 (14) |
C4f | 0.0465 (14) | 0.0517 (17) | 0.0614 (17) | 0.0008 (13) | 0.0080 (12) | −0.0053 (14) |
C5f | 0.0582 (17) | 0.0434 (17) | 0.0679 (19) | 0.0047 (13) | 0.0076 (14) | 0.0023 (14) |
C6f | 0.0550 (17) | 0.0518 (18) | 0.0577 (16) | 0.0047 (13) | 0.0086 (13) | 0.0070 (15) |
C7f | 0.082 (2) | 0.070 (2) | 0.073 (2) | 0.0021 (18) | 0.0113 (18) | −0.0166 (18) |
Geometric parameters (Å, º) top
N1—C5 | 1.302 (4) | C5p—H5p | 0.9300 |
N1—N2 | 1.381 (3) | C6p—H6p | 0.9300 |
N2—C3 | 1.301 (3) | C1f—C2f | 1.371 (4) |
C3—N4 | 1.366 (3) | C1f—C6f | 1.376 (4) |
C3—C4p | 1.479 (4) | C2f—C3f | 1.369 (4) |
N4—C5 | 1.362 (3) | C2f—H2f | 0.9300 |
N4—C1f | 1.439 (3) | C3f—C4f | 1.390 (4) |
C5—H5 | 0.9300 | C3f—H3f | 0.9300 |
N1p—C6p | 1.328 (4) | C4f—C5f | 1.376 (4) |
N1p—C2p | 1.331 (4) | C4f—C7f | 1.500 (4) |
C2p—C3p | 1.375 (4) | C5f—C6f | 1.377 (4) |
C2p—H2p | 0.9300 | C5f—H5f | 0.9300 |
C3p—C4p | 1.375 (4) | C6f—H6f | 0.9300 |
C3p—H3p | 0.9300 | C7f—H7f1 | 0.9600 |
C4p—C5p | 1.382 (4) | C7f—H7f2 | 0.9600 |
C5p—C6p | 1.382 (4) | C7f—H7f3 | 0.9600 |
| | | |
C5—N1—N2 | 106.6 (2) | C5p—C6p—H6p | 118.0 |
C3—N2—N1 | 107.9 (2) | C2f—C1f—C6f | 120.2 (3) |
N2—C3—N4 | 110.2 (2) | C2f—C1f—N4 | 119.8 (3) |
N2—C3—C4p | 123.3 (2) | C6f—C1f—N4 | 119.9 (2) |
N4—C3—C4p | 126.5 (2) | C3f—C2f—C1f | 120.0 (3) |
C5—N4—C3 | 104.1 (2) | C3f—C2f—H2f | 120.0 |
C5—N4—C1f | 124.6 (2) | C1f—C2f—H2f | 120.0 |
C3—N4—C1f | 130.8 (2) | C2f—C3f—C4f | 121.3 (3) |
N1—C5—N4 | 111.1 (3) | C2f—C3f—H3f | 119.3 |
N1—C5—H5 | 124.4 | C4f—C3f—H3f | 119.3 |
N4—C5—H5 | 124.4 | C5f—C4f—C3f | 117.4 (3) |
C6p—N1p—C2p | 116.0 (3) | C5f—C4f—C7f | 121.2 (3) |
N1p—C2p—C3p | 124.5 (3) | C3f—C4f—C7f | 121.4 (3) |
N1p—C2p—H2p | 117.8 | C4f—C5f—C6f | 122.1 (3) |
C3p—C2p—H2p | 117.8 | C4f—C5f—H5f | 119.0 |
C2p—C3p—C4p | 118.9 (3) | C6f—C5f—H5f | 119.0 |
C2p—C3p—H3p | 120.6 | C1f—C6f—C5f | 119.1 (3) |
C4p—C3p—H3p | 120.6 | C1f—C6f—H6f | 120.5 |
C3p—C4p—C5p | 117.7 (3) | C5f—C6f—H6f | 120.5 |
C3p—C4p—C3 | 123.9 (3) | C4f—C7f—H7f1 | 109.5 |
C5p—C4p—C3 | 118.3 (3) | C4f—C7f—H7f2 | 109.5 |
C6p—C5p—C4p | 119.0 (3) | H7f1—CfF—H7f2 | 109.5 |
C6p—C5p—H5p | 120.5 | C4f—C7f—H7f3 | 109.5 |
C4p—C5p—H5p | 120.5 | H7f1—C7f—H7f3 | 109.5 |
N1p—C6p—C5p | 123.9 (3) | H7f2—C7f—H7f3 | 109.5 |
N1p—C6p—H6p | 118.0 | | |
| | | |
C5—N1—N2—C3 | 0.3 (3) | C3p—C4p—C5p—C6p | −0.2 (4) |
N1—N2—C3—N4 | 0.2 (3) | C3—C4p—C5p—C6p | −177.2 (3) |
N1—N2—C3—C4p | 179.8 (3) | C2p—N1p—C6p—C5p | 1.2 (5) |
N2—C3—N4—C5 | −0.7 (3) | C4p—C5p—C6p—N1p | −1.1 (5) |
C4p—C3—N4—C5 | 179.8 (3) | C5—N4—C1f—C2f | −107.7 (3) |
N2—C3—N4—C1f | −172.5 (3) | C3—N4—C1f—C2f | 62.6 (4) |
C4p—C3—N4—C1f | 8.0 (5) | C5—N4—C1f—C6f | 69.2 (4) |
N2—N1—C5—N4 | −0.7 (3) | C3—N4—C1f—C6f | −120.4 (3) |
C3—N4—C5—N1 | 0.9 (3) | C6f—C1f—C2f—C3f | −1.4 (4) |
C1f—N4—C5—N1 | 173.3 (2) | N4—C1f—C2f—C3f | 175.5 (3) |
C6p—N1p—C2p—C3p | −0.1 (5) | C1f—C2f—C3f—C4f | −0.1 (5) |
N1p—C2p—C3p—C4p | −1.0 (5) | C2f—C3f—C4f—C5f | 1.5 (4) |
C2p—C3p—C4p—C5p | 1.1 (4) | C2f—C3f—C4f—C7f | −177.0 (3) |
C2p—C3p—C4p—C3 | 178.0 (3) | C3f—C4f—C5f—C6f | −1.3 (4) |
N2—C3—C4p—C3p | −152.8 (3) | C7f—C4f—C5f—C6f | 177.2 (3) |
N4—C3—C4p—C3p | 26.7 (5) | C2f—C1f—C6f—C5f | 1.6 (4) |
N2—C3—C4p—C5p | 24.1 (4) | N4—C1f—C6f—C5f | −175.4 (2) |
N4—C3—C4p—C5p | −156.4 (3) | C4f—C5f—C6f—C1f | −0.2 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···N1i | 0.93 | 2.65 | 3.522 (4) | 157 |
C5f—H5f···N1pii | 0.93 | 2.93 | 3.536 (4) | 124 |
C7f—H7f3···N1pii | 0.96 | 2.87 | 3.673 (5) | 142 |
C5p—H5p···N1iii | 0.93 | 2.96 | 3.477 (4) | 117 |
C5p—H5p···N2iii | 0.93 | 2.96 | 3.743 (4) | 143 |
C6p—H6p···N1iii | 0.93 | 2.95 | 3.490 (4) | 119 |
C6f—H6f···N2iv | 0.93 | 2.98 | 3.603 (4) | 126 |
C3f—H3f···πv | 0.93 | 2.94 | 3.850 (4) | 168 |
C5f—H5f···πiv | 0.93 | 3.02 | 3.820 (4) | 145 |
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) x+1, y−1, z; (iii) −x+1, y+1/2, −z+3/2; (iv) x, y−1, z; (v) −x+1, −y+1, −z+1. |
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