Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025986/hb2428sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025986/hb2428Isup2.hkl |
CCDC reference: 652071
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.106
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C5 - C6 .. 5.27 su
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was prepared according to the procedure reported by Huang & Wang (1992) and purified by recrystallization from ethyl acetate in 82.7% yield; mp 438–440 K; FT—IR (KBr): 3369.03, 1636.30, 1588.09, 1526.38, 1428.03 cm-1.1H NMR (CDCl3, δp.p.m.): 8.60–8.57 (d, 2H, aryl H), 7.74–7.71 (d, 2H, aryl H), 7.67–7.65 (d, 2H, aryl H), 7.49–7.44(t, 2H, aryl H), 7.41–7.36 (t, 1H, aryl H), 6.73 (s, 1H, NH), 4.41–4.36 (t, 2H, CH2); 3.56–3.51 (m, 2H, CH2), 2.25–2.18 (m, 2H, CH2); 13C NMR (CDCl3, δp.p.m.): 185.18, 146.12, 144.95, 140.35, 136.02, 130.60, 128.90, 128.74, 127.98, 127.33, 126.95, 43.23, 38.66, 20.60; MS (EI) m/z: 305([M+H]+), 304 ([M]+). Anal. Calcd. For C18H16N4O: C, 71.04; H, 5.30; N, 18.41. Found: C, 70.53; H, 5.23; N, 21.18.50.
The N-bound hydrogen atom was located in a difference map and its position and Uiso value were freely refined. The C-bound H atoms were geometrically placed (C—H = 0.95–1.00 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).
Heterocyclic ketene aminals, also named cyclic 1,1-enediamines, are useful building blocks in organic synthesis, especially for the synthesis of more complex heterocycles (Huang & Wang, 1994). The title compound, (I) (Fig. 1), belongs to the family of 1, 2,3-triazole fused 1,3-diazoheterocles and its structure is described here.
The dihedral angle between the N3C2 ring and the C7—C12 benzene ring is 12.62 (9)°. The dihedral angle between the two bezene rings (C7—C12 and C13—C18) is 36.14 (9)°.
In the crystal, adjacent molecules interact by way of N—H···N hydrogen bonds (Table 1) to result in [100] chains. An intramolecular N—H···O link occurs at the same time.
For background, see: Huang & Wang, 1992; Huang & Wang, 1994.
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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, 1997); software used to prepare material for publication: SHELXTL.
Fig. 1. Molecular structure of (I) showing 30% displacement ellipsoids (arbirary spheres for the H atoms). | |
Fig. 2. Packing diagram of (I) viewed down the a-axis. |
C18H16N4O | Dx = 1.345 Mg m−3 |
Mr = 304.35 | Melting point = 438–440 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
a = 12.923 (3) Å | Cell parameters from 2403 reflections |
b = 7.3253 (17) Å | θ = 3.2–21.2° |
c = 31.765 (7) Å | µ = 0.09 mm−1 |
V = 3007.0 (12) Å3 | T = 294 K |
Z = 8 | Prism, colourless |
F(000) = 1280 | 0.24 × 0.20 × 0.14 mm |
Bruker SMART CCD diffractometer | 3066 independent reflections |
Radiation source: fine-focus sealed tube | 1804 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
ω scans | θmax = 26.4°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −16→16 |
Tmin = 0.979, Tmax = 0.988 | k = −9→9 |
16020 measured reflections | l = −26→39 |
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)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.0465P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
3066 reflections | Δρmax = 0.17 e Å−3 |
213 parameters | Δρmin = −0.13 e Å−3 |
1 restraint | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0087 (8) |
C18H16N4O | V = 3007.0 (12) Å3 |
Mr = 304.35 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 12.923 (3) Å | µ = 0.09 mm−1 |
b = 7.3253 (17) Å | T = 294 K |
c = 31.765 (7) Å | 0.24 × 0.20 × 0.14 mm |
Bruker SMART CCD diffractometer | 3066 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 1804 reflections with I > 2σ(I) |
Tmin = 0.979, Tmax = 0.988 | Rint = 0.074 |
16020 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 1 restraint |
wR(F2) = 0.106 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.17 e Å−3 |
3066 reflections | Δρmin = −0.13 e Å−3 |
213 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.27429 (9) | 0.3111 (2) | 0.43106 (4) | 0.0629 (4) | |
N1 | 0.20844 (11) | 0.2160 (2) | 0.51324 (5) | 0.0447 (4) | |
H1 | 0.2688 (9) | 0.216 (3) | 0.4990 (5) | 0.064 (6)* | |
N2 | 0.02806 (9) | 0.23953 (18) | 0.50904 (4) | 0.0361 (4) | |
N3 | −0.04815 (10) | 0.2859 (2) | 0.48069 (5) | 0.0441 (4) | |
N4 | −0.00221 (10) | 0.3245 (2) | 0.44527 (5) | 0.0412 (4) | |
C1 | 0.20019 (13) | 0.1494 (3) | 0.55610 (5) | 0.0438 (5) | |
H1A | 0.2627 | 0.1791 | 0.5715 | 0.053* | |
H1B | 0.1923 | 0.0177 | 0.5560 | 0.053* | |
C2 | 0.10745 (12) | 0.2368 (3) | 0.57734 (5) | 0.0422 (5) | |
H2A | 0.1179 | 0.3677 | 0.5791 | 0.051* | |
H2B | 0.1010 | 0.1899 | 0.6058 | 0.051* | |
C3 | 0.00857 (12) | 0.1979 (2) | 0.55315 (5) | 0.0414 (5) | |
H3A | −0.0108 | 0.0707 | 0.5563 | 0.050* | |
H3B | −0.0474 | 0.2731 | 0.5638 | 0.050* | |
C4 | 0.12182 (11) | 0.2518 (2) | 0.49126 (5) | 0.0348 (4) | |
C5 | 0.10309 (12) | 0.3075 (2) | 0.45001 (5) | 0.0347 (4) | |
C6 | 0.18455 (13) | 0.3375 (2) | 0.41932 (5) | 0.0401 (5) | |
C7 | 0.16573 (13) | 0.3949 (2) | 0.37498 (5) | 0.0364 (4) | |
C8 | 0.24826 (13) | 0.3823 (3) | 0.34710 (6) | 0.0474 (5) | |
H8 | 0.3119 | 0.3404 | 0.3568 | 0.057* | |
C9 | 0.23771 (14) | 0.4304 (3) | 0.30551 (6) | 0.0496 (5) | |
H9 | 0.2944 | 0.4203 | 0.2876 | 0.059* | |
C10 | 0.14424 (13) | 0.4939 (2) | 0.28949 (6) | 0.0401 (5) | |
C11 | 0.06187 (13) | 0.5085 (2) | 0.31750 (6) | 0.0444 (5) | |
H11 | −0.0015 | 0.5517 | 0.3079 | 0.053* | |
C12 | 0.07241 (13) | 0.4601 (3) | 0.35947 (5) | 0.0421 (5) | |
H12 | 0.0161 | 0.4715 | 0.3775 | 0.050* | |
C13 | 0.13337 (14) | 0.5414 (2) | 0.24429 (6) | 0.0431 (5) | |
C14 | 0.21450 (16) | 0.6219 (3) | 0.22220 (6) | 0.0561 (6) | |
H14 | 0.2765 | 0.6462 | 0.2360 | 0.067* | |
C15 | 0.20419 (19) | 0.6662 (3) | 0.18004 (7) | 0.0658 (6) | |
H15 | 0.2592 | 0.7198 | 0.1657 | 0.079* | |
C16 | 0.11331 (19) | 0.6316 (3) | 0.15926 (7) | 0.0665 (6) | |
H16 | 0.1061 | 0.6630 | 0.1310 | 0.080* | |
C17 | 0.03321 (18) | 0.5504 (3) | 0.18044 (7) | 0.0697 (7) | |
H17 | −0.0283 | 0.5251 | 0.1664 | 0.084* | |
C18 | 0.04299 (16) | 0.5058 (3) | 0.22242 (6) | 0.0578 (6) | |
H18 | −0.0122 | 0.4508 | 0.2363 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0297 (8) | 0.1105 (13) | 0.0485 (8) | 0.0093 (7) | −0.0012 (6) | 0.0123 (8) |
N1 | 0.0269 (8) | 0.0697 (11) | 0.0377 (9) | 0.0051 (7) | 0.0009 (7) | 0.0067 (8) |
N2 | 0.0246 (8) | 0.0471 (9) | 0.0367 (8) | −0.0010 (6) | 0.0008 (6) | 0.0018 (7) |
N3 | 0.0288 (8) | 0.0592 (10) | 0.0441 (9) | −0.0002 (7) | −0.0015 (7) | 0.0047 (8) |
N4 | 0.0298 (8) | 0.0524 (9) | 0.0414 (9) | −0.0004 (7) | −0.0001 (7) | 0.0032 (8) |
C1 | 0.0391 (11) | 0.0499 (11) | 0.0425 (11) | 0.0044 (9) | −0.0029 (9) | 0.0072 (9) |
C2 | 0.0391 (11) | 0.0497 (11) | 0.0380 (11) | 0.0010 (9) | 0.0003 (8) | 0.0060 (9) |
C3 | 0.0345 (10) | 0.0491 (11) | 0.0407 (11) | −0.0023 (8) | 0.0079 (9) | 0.0042 (9) |
C4 | 0.0262 (9) | 0.0401 (10) | 0.0382 (10) | 0.0004 (8) | −0.0002 (8) | −0.0018 (9) |
C5 | 0.0268 (10) | 0.0415 (10) | 0.0357 (10) | 0.0021 (7) | 0.0003 (8) | 0.0012 (9) |
C6 | 0.0306 (10) | 0.0490 (11) | 0.0408 (11) | 0.0033 (8) | −0.0022 (8) | −0.0024 (9) |
C7 | 0.0313 (10) | 0.0403 (10) | 0.0376 (10) | 0.0000 (8) | −0.0003 (8) | −0.0013 (8) |
C8 | 0.0342 (10) | 0.0647 (13) | 0.0433 (12) | 0.0079 (9) | 0.0035 (9) | 0.0033 (10) |
C9 | 0.0417 (11) | 0.0667 (14) | 0.0402 (12) | 0.0065 (10) | 0.0114 (9) | 0.0015 (10) |
C10 | 0.0404 (11) | 0.0403 (11) | 0.0395 (11) | −0.0009 (8) | 0.0013 (9) | −0.0023 (9) |
C11 | 0.0364 (11) | 0.0568 (13) | 0.0399 (11) | 0.0057 (9) | −0.0043 (9) | 0.0021 (10) |
C12 | 0.0337 (10) | 0.0547 (12) | 0.0379 (11) | 0.0031 (9) | 0.0047 (8) | −0.0005 (9) |
C13 | 0.0505 (12) | 0.0409 (10) | 0.0378 (11) | 0.0021 (9) | 0.0016 (9) | −0.0019 (9) |
C14 | 0.0590 (13) | 0.0658 (14) | 0.0436 (13) | −0.0082 (11) | 0.0040 (10) | 0.0016 (11) |
C15 | 0.0825 (17) | 0.0672 (15) | 0.0479 (14) | −0.0052 (12) | 0.0184 (12) | 0.0065 (12) |
C16 | 0.0975 (19) | 0.0633 (15) | 0.0388 (13) | 0.0091 (13) | −0.0009 (13) | 0.0025 (11) |
C17 | 0.0766 (17) | 0.0841 (17) | 0.0485 (15) | −0.0029 (14) | −0.0138 (12) | 0.0020 (13) |
C18 | 0.0586 (14) | 0.0693 (15) | 0.0457 (13) | −0.0078 (11) | −0.0065 (10) | 0.0068 (11) |
O1—C6 | 1.2333 (19) | C7—C8 | 1.389 (2) |
N1—C4 | 1.345 (2) | C8—C9 | 1.374 (2) |
N1—C1 | 1.450 (2) | C8—H8 | 0.9300 |
N1—H1 | 0.901 (9) | C9—C10 | 1.391 (2) |
N2—C4 | 1.3398 (18) | C9—H9 | 0.9300 |
N2—N3 | 1.3772 (18) | C10—C11 | 1.391 (2) |
N2—C3 | 1.456 (2) | C10—C13 | 1.484 (2) |
N3—N4 | 1.3032 (19) | C11—C12 | 1.386 (2) |
N4—C5 | 1.3748 (19) | C11—H11 | 0.9300 |
C1—C2 | 1.517 (2) | C12—H12 | 0.9300 |
C1—H1A | 0.9700 | C13—C18 | 1.384 (2) |
C1—H1B | 0.9700 | C13—C14 | 1.392 (2) |
C2—C3 | 1.518 (2) | C14—C15 | 1.384 (3) |
C2—H2A | 0.9700 | C14—H14 | 0.9300 |
C2—H2B | 0.9700 | C15—C16 | 1.371 (3) |
C3—H3A | 0.9700 | C15—H15 | 0.9300 |
C3—H3B | 0.9700 | C16—C17 | 1.370 (3) |
C4—C5 | 1.394 (2) | C16—H16 | 0.9300 |
C5—C6 | 1.452 (2) | C17—C18 | 1.379 (3) |
C6—C7 | 1.490 (2) | C17—H17 | 0.9300 |
C7—C12 | 1.387 (2) | C18—H18 | 0.9300 |
C4—N1—C1 | 119.45 (14) | C12—C7—C6 | 125.08 (15) |
C4—N1—H1 | 117.4 (12) | C8—C7—C6 | 117.28 (15) |
C1—N1—H1 | 122.2 (12) | C9—C8—C7 | 121.30 (17) |
C4—N2—N3 | 110.76 (13) | C9—C8—H8 | 119.4 |
C4—N2—C3 | 125.19 (14) | C7—C8—H8 | 119.4 |
N3—N2—C3 | 123.87 (13) | C8—C9—C10 | 121.58 (17) |
N4—N3—N2 | 107.00 (13) | C8—C9—H9 | 119.2 |
N3—N4—C5 | 109.68 (13) | C10—C9—H9 | 119.2 |
N1—C1—C2 | 109.48 (14) | C9—C10—C11 | 117.15 (17) |
N1—C1—H1A | 109.8 | C9—C10—C13 | 120.98 (17) |
C2—C1—H1A | 109.8 | C11—C10—C13 | 121.87 (17) |
N1—C1—H1B | 109.8 | C12—C11—C10 | 121.33 (17) |
C2—C1—H1B | 109.8 | C12—C11—H11 | 119.3 |
H1A—C1—H1B | 108.2 | C10—C11—H11 | 119.3 |
C1—C2—C3 | 111.13 (15) | C11—C12—C7 | 120.99 (16) |
C1—C2—H2A | 109.4 | C11—C12—H12 | 119.5 |
C3—C2—H2A | 109.4 | C7—C12—H12 | 119.5 |
C1—C2—H2B | 109.4 | C18—C13—C14 | 117.54 (18) |
C3—C2—H2B | 109.4 | C18—C13—C10 | 121.41 (17) |
H2A—C2—H2B | 108.0 | C14—C13—C10 | 121.04 (17) |
N2—C3—C2 | 107.59 (13) | C15—C14—C13 | 120.9 (2) |
N2—C3—H3A | 110.2 | C15—C14—H14 | 119.5 |
C2—C3—H3A | 110.2 | C13—C14—H14 | 119.5 |
N2—C3—H3B | 110.2 | C16—C15—C14 | 120.3 (2) |
C2—C3—H3B | 110.2 | C16—C15—H15 | 119.8 |
H3A—C3—H3B | 108.5 | C14—C15—H15 | 119.8 |
N2—C4—N1 | 121.38 (15) | C17—C16—C15 | 119.4 (2) |
N2—C4—C5 | 105.01 (13) | C17—C16—H16 | 120.3 |
N1—C4—C5 | 133.60 (15) | C15—C16—H16 | 120.3 |
N4—C5—C4 | 107.54 (14) | C16—C17—C18 | 120.6 (2) |
N4—C5—C6 | 129.10 (15) | C16—C17—H17 | 119.7 |
C4—C5—C6 | 123.35 (14) | C18—C17—H17 | 119.7 |
O1—C6—C5 | 117.08 (16) | C17—C18—C13 | 121.2 (2) |
O1—C6—C7 | 118.91 (15) | C17—C18—H18 | 119.4 |
C5—C6—C7 | 124.00 (15) | C13—C18—H18 | 119.4 |
C12—C7—C8 | 117.64 (16) | ||
C4—N2—N3—N4 | 0.80 (19) | C5—C6—C7—C12 | 12.9 (3) |
C3—N2—N3—N4 | 176.12 (15) | O1—C6—C7—C8 | 11.9 (3) |
N2—N3—N4—C5 | −1.06 (18) | C5—C6—C7—C8 | −167.19 (16) |
C4—N1—C1—C2 | −35.0 (2) | C12—C7—C8—C9 | −0.8 (3) |
N1—C1—C2—C3 | 57.67 (19) | C6—C7—C8—C9 | 179.30 (17) |
C4—N2—C3—C2 | 19.5 (2) | C7—C8—C9—C10 | 0.0 (3) |
N3—N2—C3—C2 | −155.16 (15) | C8—C9—C10—C11 | 0.7 (3) |
C1—C2—C3—N2 | −48.84 (19) | C8—C9—C10—C13 | −178.63 (18) |
N3—N2—C4—N1 | 178.77 (15) | C9—C10—C11—C12 | −0.6 (3) |
C3—N2—C4—N1 | 3.5 (3) | C13—C10—C11—C12 | 178.66 (17) |
N3—N2—C4—C5 | −0.22 (18) | C10—C11—C12—C7 | −0.1 (3) |
C3—N2—C4—C5 | −175.46 (15) | C8—C7—C12—C11 | 0.8 (3) |
C1—N1—C4—N2 | 4.8 (3) | C6—C7—C12—C11 | −179.28 (17) |
C1—N1—C4—C5 | −176.54 (18) | C9—C10—C13—C18 | 143.17 (19) |
N3—N4—C5—C4 | 0.94 (19) | C11—C10—C13—C18 | −36.1 (3) |
N3—N4—C5—C6 | −179.67 (17) | C9—C10—C13—C14 | −36.1 (3) |
N2—C4—C5—N4 | −0.42 (18) | C11—C10—C13—C14 | 144.62 (19) |
N1—C4—C5—N4 | −179.23 (18) | C18—C13—C14—C15 | 0.7 (3) |
N2—C4—C5—C6 | −179.84 (15) | C10—C13—C14—C15 | −179.97 (18) |
N1—C4—C5—C6 | 1.3 (3) | C13—C14—C15—C16 | 0.1 (3) |
N4—C5—C6—O1 | −179.20 (16) | C14—C15—C16—C17 | −0.9 (3) |
C4—C5—C6—O1 | 0.1 (3) | C15—C16—C17—C18 | 0.9 (3) |
N4—C5—C6—C7 | −0.1 (3) | C16—C17—C18—C13 | 0.0 (3) |
C4—C5—C6—C7 | 179.24 (16) | C14—C13—C18—C17 | −0.8 (3) |
O1—C6—C7—C12 | −167.97 (17) | C10—C13—C18—C17 | 179.95 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.90 (1) | 2.27 (2) | 2.833 (2) | 120 (1) |
N1—H1···N3i | 0.90 (1) | 2.45 (1) | 3.152 (2) | 135 (1) |
Symmetry code: (i) x+1/2, −y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C18H16N4O |
Mr | 304.35 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 294 |
a, b, c (Å) | 12.923 (3), 7.3253 (17), 31.765 (7) |
V (Å3) | 3007.0 (12) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.24 × 0.20 × 0.14 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.979, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16020, 3066, 1804 |
Rint | 0.074 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.106, 1.03 |
No. of reflections | 3066 |
No. of parameters | 213 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.13 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.902 (13) | 2.269 (17) | 2.833 (2) | 120.3 (12) |
N1—H1···N3i | 0.902 (13) | 2.452 (12) | 3.152 (2) | 134.6 (13) |
Symmetry code: (i) x+1/2, −y+1/2, −z+1. |
Heterocyclic ketene aminals, also named cyclic 1,1-enediamines, are useful building blocks in organic synthesis, especially for the synthesis of more complex heterocycles (Huang & Wang, 1994). The title compound, (I) (Fig. 1), belongs to the family of 1, 2,3-triazole fused 1,3-diazoheterocles and its structure is described here.
The dihedral angle between the N3C2 ring and the C7—C12 benzene ring is 12.62 (9)°. The dihedral angle between the two bezene rings (C7—C12 and C13—C18) is 36.14 (9)°.
In the crystal, adjacent molecules interact by way of N—H···N hydrogen bonds (Table 1) to result in [100] chains. An intramolecular N—H···O link occurs at the same time.