In the title compound, C17H19N5, the almost ideally planar triazole ring forms a dihedral angle of 75.1 (1)° with the benzene ring. There are intermolecular π–π interactions.
Supporting information
CCDC reference: 282554
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.063
- wR factor = 0.203
- Data-to-parameter ratio = 16.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for C14 - C15 .. 6.16 su
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. N3 .. 2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. N5 .. 2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H162 .. N4 .. 2.74 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
0 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
Crystal data top
C17H19N5 | F(000) = 1248.00 |
Mr = 293.37 | Dx = 1.196 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -C 2yc | Cell parameters from 10339 reflections |
a = 17.9107 (8) Å | θ = 2.2–27.5° |
b = 11.2522 (3) Å | µ = 0.08 mm−1 |
c = 18.9011 (7) Å | T = 295 K |
β = 121.181 (1)° | Prism, colorless |
V = 3258.9 (2) Å3 | 0.45 × 0.45 × 0.20 mm |
Z = 8 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | Rint = 0.031 |
Detector resolution: 10.00 pixels mm-1 | θmax = 27.5° |
ω scans | h = −23→23 |
16052 measured reflections | k = −14→14 |
3748 independent reflections | l = −23→24 |
2348 reflections with F2 > 2σ(F2) | |
Refinement top
Refinement on F2 | w = 1/[0.0057Fo2 + σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.063 | (Δ/σ)max < 0.001 |
wR(F2) = 0.203 | Δρmax = 0.37 e Å−3 |
S = 1.00 | Δρmin = −0.37 e Å−3 |
3197 reflections | Extinction correction: Larson (1970) |
200 parameters | Extinction coefficient: 184 (57) |
H-atom parameters constrained | |
Special details top
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and
goodness of fit (S) are based on F2. R-factor (gt) are
based on F. The threshold expression of F2 > 2.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.7456 (1) | 0.1178 (1) | 0.7652 (1) | 0.0360 (4) | |
N2 | 0.7743 (1) | 0.0422 (2) | 0.7282 (1) | 0.0510 (6) | |
N3 | 0.8292 (1) | 0.2258 (2) | 0.7384 (1) | 0.0557 (6) | |
N4 | 0.2402 (1) | −0.0849 (2) | 0.5292 (2) | 0.0615 (7) | |
N5 | 0.2937 (2) | 0.3453 (2) | 0.5999 (1) | 0.0592 (7) | |
C1 | 0.5897 (1) | 0.0883 (2) | 0.7136 (1) | 0.0319 (5) | |
C2 | 0.5404 (1) | −0.0125 (2) | 0.6766 (1) | 0.0321 (5) | |
C3 | 0.4549 (1) | −0.0020 (2) | 0.6094 (1) | 0.0304 (5) | |
C4 | 0.4211 (1) | 0.1102 (2) | 0.5808 (1) | 0.0335 (5) | |
C5 | 0.4705 (1) | 0.2123 (2) | 0.6173 (1) | 0.0325 (5) | |
C6 | 0.5545 (1) | 0.2000 (2) | 0.6839 (1) | 0.0345 (5) | |
C7 | 0.6823 (1) | 0.0774 (2) | 0.7863 (1) | 0.0363 (5) | |
C8 | 0.8238 (2) | 0.1121 (2) | 0.7143 (2) | 0.0558 (8) | |
C9 | 0.7789 (1) | 0.2252 (2) | 0.7703 (1) | 0.0479 (6) | |
C10 | 0.4007 (1) | −0.1125 (2) | 0.5638 (1) | 0.0351 (5) | |
C11 | 0.3100 (1) | −0.0957 (2) | 0.5445 (1) | 0.0395 (6) | |
C12 | 0.3976 (2) | −0.1256 (3) | 0.4815 (2) | 0.0635 (9) | |
C13 | 0.4339 (2) | −0.2265 (2) | 0.6156 (2) | 0.0579 (7) | |
C14 | 0.4292 (1) | 0.3347 (2) | 0.5820 (1) | 0.0382 (5) | |
C15 | 0.3516 (2) | 0.3423 (2) | 0.5906 (1) | 0.0418 (6) | |
C16 | 0.3987 (2) | 0.3435 (2) | 0.4899 (2) | 0.0564 (8) | |
C17 | 0.4894 (2) | 0.4392 (2) | 0.6296 (2) | 0.0668 (8) | |
H2 | 0.5641 | −0.0873 | 0.6966 | 0.038* | |
H4 | 0.3643 | 0.1177 | 0.5363 | 0.038* | |
H6 | 0.5879 | 0.2674 | 0.7091 | 0.040* | |
H71 | 0.6933 | −0.0019 | 0.8024 | 0.040* | |
H72 | 0.6880 | 0.1231 | 0.8299 | 0.041* | |
H8 | 0.8532 | 0.0849 | 0.6889 | 0.071* | |
H9 | 0.7678 | 0.2913 | 0.7930 | 0.057* | |
H121 | 0.3497 | −0.0845 | 0.4402 | 0.081* | |
H122 | 0.3928 | −0.2056 | 0.4674 | 0.080* | |
H123 | 0.4485 | −0.0947 | 0.4869 | 0.080* | |
H131 | 0.4747 | −0.2630 | 0.6063 | 0.060* | |
H132 | 0.3873 | −0.2779 | 0.6004 | 0.060* | |
H133 | 0.4599 | −0.2078 | 0.6714 | 0.060* | |
H161 | 0.4438 | 0.3730 | 0.4841 | 0.071* | |
H162 | 0.3511 | 0.3945 | 0.4639 | 0.071* | |
H163 | 0.3826 | 0.2686 | 0.4658 | 0.071* | |
H171 | 0.4804 | 0.4623 | 0.6718 | 0.074* | |
H172 | 0.4770 | 0.5025 | 0.5935 | 0.073* | |
H173 | 0.5473 | 0.4163 | 0.6520 | 0.074* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0270 (9) | 0.0365 (9) | 0.0365 (9) | −0.0012 (7) | 0.0108 (7) | −0.0033 (7) |
N2 | 0.051 (1) | 0.043 (1) | 0.069 (1) | 0.0026 (9) | 0.038 (1) | −0.0048 (9) |
N3 | 0.048 (1) | 0.054 (1) | 0.067 (1) | −0.012 (1) | 0.031 (1) | −0.006 (1) |
N4 | 0.032 (1) | 0.049 (1) | 0.092 (2) | −0.0049 (9) | 0.024 (1) | −0.016 (1) |
N5 | 0.058 (1) | 0.057 (1) | 0.073 (2) | 0.015 (1) | 0.042 (1) | 0.006 (1) |
C1 | 0.026 (1) | 0.035 (1) | 0.033 (1) | 0.0006 (8) | 0.0140 (8) | 0.0017 (8) |
C2 | 0.031 (1) | 0.0281 (9) | 0.037 (1) | 0.0048 (7) | 0.0175 (9) | 0.0055 (8) |
C3 | 0.028 (1) | 0.0277 (9) | 0.035 (1) | −0.0009 (7) | 0.0156 (8) | −0.0018 (7) |
C4 | 0.027 (1) | 0.032 (1) | 0.036 (1) | 0.0020 (8) | 0.0126 (8) | 0.0008 (8) |
C5 | 0.030 (1) | 0.029 (1) | 0.038 (1) | 0.0014 (8) | 0.0170 (8) | 0.0001 (8) |
C6 | 0.031 (1) | 0.030 (1) | 0.040 (1) | −0.0039 (8) | 0.0162 (9) | −0.0020 (8) |
C7 | 0.029 (1) | 0.040 (1) | 0.032 (1) | −0.0015 (8) | 0.0103 (8) | 0.0022 (8) |
C8 | 0.050 (2) | 0.058 (1) | 0.069 (2) | 0.001 (1) | 0.038 (1) | −0.000 (1) |
C9 | 0.042 (1) | 0.044 (1) | 0.055 (1) | −0.010 (1) | 0.023 (1) | −0.009 (1) |
C10 | 0.031 (1) | 0.027 (1) | 0.044 (1) | −0.0009 (8) | 0.0173 (9) | −0.0038 (8) |
C11 | 0.034 (1) | 0.030 (1) | 0.048 (1) | −0.0052 (8) | 0.0168 (9) | −0.0078 (8) |
C12 | 0.070 (2) | 0.066 (2) | 0.063 (2) | −0.016 (1) | 0.041 (2) | −0.025 (1) |
C13 | 0.038 (1) | 0.028 (1) | 0.082 (2) | −0.0019 (9) | 0.013 (1) | −0.000 (1) |
C14 | 0.035 (1) | 0.027 (1) | 0.050 (1) | 0.0040 (8) | 0.020 (1) | 0.0042 (9) |
C15 | 0.043 (1) | 0.031 (1) | 0.047 (1) | 0.0103 (9) | 0.020 (1) | 0.0055 (9) |
C16 | 0.071 (2) | 0.045 (1) | 0.060 (1) | 0.021 (1) | 0.039 (1) | 0.022 (1) |
C17 | 0.059 (2) | 0.028 (1) | 0.096 (2) | −0.001 (1) | 0.027 (2) | −0.002 (1) |
Geometric parameters (Å, º) top
N1—N2 | 1.360 (3) | C14—C16 | 1.534 (4) |
N1—C7 | 1.455 (4) | C14—C17 | 1.533 (3) |
N1—C9 | 1.329 (3) | C2—H2 | 0.9300 |
N2—C8 | 1.309 (4) | C4—H4 | 0.9300 |
N3—C8 | 1.344 (4) | C6—H6 | 0.9300 |
N3—C9 | 1.319 (5) | C7—H71 | 0.9300 |
N4—C11 | 1.135 (4) | C7—H72 | 0.9300 |
N5—C15 | 1.138 (5) | C8—H8 | 0.9300 |
C1—C2 | 1.384 (3) | C9—H9 | 0.9300 |
C1—C6 | 1.388 (3) | C12—H121 | 0.9300 |
C1—C7 | 1.516 (2) | C12—H122 | 0.9300 |
C2—C3 | 1.401 (2) | C12—H123 | 0.9300 |
C3—C4 | 1.384 (3) | C13—H131 | 0.9300 |
C3—C10 | 1.537 (3) | C13—H132 | 0.9300 |
C4—C5 | 1.395 (3) | C13—H133 | 0.9300 |
C5—C6 | 1.380 (2) | C16—H161 | 0.9300 |
C5—C14 | 1.543 (3) | C16—H162 | 0.9300 |
C10—C11 | 1.482 (4) | C16—H163 | 0.9300 |
C10—C12 | 1.535 (5) | C17—H171 | 0.9300 |
C10—C13 | 1.534 (3) | C17—H172 | 0.9300 |
C14—C15 | 1.483 (4) | C17—H173 | 0.9300 |
| | | |
C7—N1—N2 | 120.1 (2) | N2—C8—H8 | 121.9581 |
N1—N2—C8 | 101.7 (2) | N3—C8—H8 | 121.8270 |
C9—N1—N2 | 109.3 (2) | N3—C9—H9 | 124.4928 |
N1—C7—C1 | 111.6 (2) | C1—C2—H2 | 120.0445 |
C9—N1—C7 | 130.4 (2) | C1—C6—H6 | 119.6146 |
N1—C9—N3 | 111.0 (2) | C1—C7—H71 | 108.7555 |
N2—C8—N3 | 116.2 (3) | C1—C7—H72 | 108.9802 |
C9—N3—C8 | 101.7 (3) | H2—C2—C3 | 119.8940 |
N4—C11—C10 | 178.7 (2) | C3—C4—H4 | 119.1821 |
N5—C15—C14 | 177.3 (2) | H4—C4—C5 | 119.3617 |
C6—C1—C2 | 120.1 (2) | C5—C6—H6 | 119.6170 |
C7—C1—C2 | 120.2 (2) | H72—C7—H71 | 109.4555 |
C1—C2—C3 | 120.1 (2) | C10—C12—H121 | 109.6657 |
C7—C1—C6 | 119.7 (2) | C10—C12—H123 | 109.3812 |
C1—C6—C5 | 120.8 (2) | C10—C12—H122 | 109.3603 |
C2—C3—C10 | 121.1 (2) | C10—C13—H132 | 109.4423 |
C2—C3—C4 | 118.8 (2) | C10—C13—H131 | 109.3421 |
C10—C3—C4 | 119.9 (1) | C10—C13—H133 | 109.6271 |
C3—C4—C5 | 121.5 (2) | H123—C12—H121 | 109.4809 |
C3—C10—C11 | 109.1 (2) | H122—C12—H121 | 109.4654 |
C3—C10—C12 | 109.1 (2) | H123—C12—H122 | 109.4736 |
C3—C10—C13 | 113.2 (1) | H132—C13—H131 | 109.4763 |
C4—C5—C6 | 118.8 (2) | H133—C13—H131 | 109.4719 |
C4—C5—C14 | 118.8 (1) | H133—C13—H132 | 109.4675 |
C14—C5—C6 | 122.4 (2) | C14—C16—H162 | 109.1765 |
C5—C14—C15 | 105.7 (2) | C14—C16—H163 | 109.5614 |
C5—C14—C16 | 111.0 (2) | C14—C16—H161 | 109.6723 |
C5—C14—C17 | 113.3 (2) | C14—C17—H171 | 109.6386 |
C12—C10—C11 | 107.6 (2) | C14—C17—H172 | 109.2013 |
C13—C10—C11 | 106.1 (2) | C14—C17—H173 | 109.5696 |
C13—C10—C12 | 111.4 (2) | H162—C16—H161 | 109.4717 |
C16—C14—C15 | 108.5 (2) | H163—C16—H161 | 109.4743 |
C17—C14—C15 | 107.8 (2) | H163—C16—H162 | 109.4707 |
C17—C14—C16 | 110.2 (2) | H172—C17—H171 | 109.4659 |
N1—C7—H71 | 108.9729 | H173—C17—H171 | 109.4728 |
N1—C7—H72 | 109.0319 | H173—C17—H172 | 109.4787 |
N1—C9—H9 | 124.4760 | | |
| | | |
C7—N1—N2—C8 | 175.7 (2) | C2—C1—C7—N1 | 113.1 (3) |
N2—N1—C7—C1 | −84.8 (2) | C1—C2—C3—C4 | 0.3 (4) |
N2—N1—C9—N3 | −0.1 (2) | C2—C3—C4—C5 | 0.3 (4) |
N1—N2—C8—N3 | −0.4 (3) | C2—C3—C10—C11 | 139.0 (2) |
C9—N3—C8—N2 | 0.3 (3) | C3—C4—C5—C6 | −0.7 (4) |
C8—N3—C9—N1 | −0.1 (2) | C4—C5—C6—C1 | 0.6 (4) |
C6—C1—C2—C3 | −0.3 (4) | C4—C5—C14—C15 | 60.2 (3) |
C2—C1—C6—C5 | −0.1 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···N3i | 0.93 | 2.68 | 3.580 (3) | 165 |
C4—H4···N5ii | 0.93 | 2.70 | 3.622 (3) | 174 |
C16—H162···N4ii | 0.93 | 2.74 | 3.573 (4) | 150 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+1/2, −y+1/2, −z+1. |