Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022830/lx2008sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022830/lx2008Isup2.hkl |
CCDC reference: 625154
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.120
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C24 H18 N8
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Li et al. (2006); Yan et al. (2005); Klingele & Brooker (2004).
Two drops of glacial acetic acid were added to a solution of 2-phenyl-1,2,3-triazole-4-carbaldehyde (0.346 g, 2 mmol) (Li et al., 2006) in absolute ethanol (20 ml), then dropwised 1,4-phenylene diamine (0.108 g, 1 mmol) in absolute ethanol (10 ml). The reaction mixture was refluxed for 0.5 hr., after cooling to room temperature,the precipitates were filtered and recrystallized: yield 91%, m.p. 475 K. Single-crystals were grown from a mixture solution of ethyl acetate and petroleum ether by slow evaporation.
All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C).
Aromatic nitrogen heterocycles are arguably the most facile and ligands used widely in coordination chemistry. Ligands based on heterocycles containing more than one nitrogen atom within the aromatic ring are capable of forming oligo- and polynuclear coordination compounds by bridging metal centres (Klingele et al., 2004). Schiff bases are condensation products of arylamines and carbonyl compounds. Unlike the aliphatic imines, these compounds are quite stable and represent versatile intermediates for preparation of a number of industrial and biological compounds, for example, arendiazonium nitrates, N-arylarencarboxamides, corresponding amines and cyanoamines, beta-lactams (Yan et al.,2005). 1,2,3-triazole and its derivatives are important in the synthesis of heteroarmatic compounds.
We report here the crystal structure of (I) (Fig. 1), synthesized by the reaction of 1,4-phenylene diamine with 2-phenyl-1,2,3-triazol-4-carbaldehyde. The bond lengths and angles in the (I), show normal values. In the crystal structure, π—π stacking interactions are observed between adjacent molecules, which is parallel (Fig. 2). The Cg1···Cg2iv distance is 3.485 (2) Å (Cg1 and Cg2 are the centroids of the N1,N2/C7,C8/N3 and C1-C6 rings; symmetry code as in Fig. 2).
For related literature, see: Li et al. (2006); Yan et al. (2005); Klingele & Brooker (2004).
Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: WinGX (Farrugia, 1998).
C24H18N8 | F(000) = 436 |
Mr = 418.46 | Dx = 1.399 Mg m−3 |
Monoclinic, P21/c | Melting point: 475 K |
Hall symbol: -p 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 17.670 (4) Å | Cell parameters from 6687 reflections |
b = 4.800 (1) Å | θ = 3.5–27.5° |
c = 11.751 (2) Å | µ = 0.09 mm−1 |
β = 94.42 (3)° | T = 153 K |
V = 993.7 (4) Å3 | Sheet, light yellow |
Z = 2 | 0.45 × 0.40 × 0.35 mm |
Rigaku R-AXIS SPIDER diffractometer | 1743 reflections with I > 2σ(I) |
Radiation source: Rotating Anode | Rint = 0.032 |
Graphite monochromator | θmax = 27.5°, θmin = 3.5° |
ω scans | h = −22→22 |
8889 measured reflections | k = −6→6 |
2273 independent reflections | l = −12→15 |
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)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0729P)2 + 0.1883P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
2273 reflections | Δρmax = 0.23 e Å−3 |
146 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: 0.026 (5) |
C24H18N8 | V = 993.7 (4) Å3 |
Mr = 418.46 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 17.670 (4) Å | µ = 0.09 mm−1 |
b = 4.800 (1) Å | T = 153 K |
c = 11.751 (2) Å | 0.45 × 0.40 × 0.35 mm |
β = 94.42 (3)° |
Rigaku R-AXIS SPIDER diffractometer | 1743 reflections with I > 2σ(I) |
8889 measured reflections | Rint = 0.032 |
2273 independent reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.23 e Å−3 |
2273 reflections | Δρmin = −0.24 e Å−3 |
146 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 | ||
N1 | 0.26955 (6) | 0.5600 (2) | 0.66669 (10) | 0.0280 (3) | |
N2 | 0.22887 (6) | 0.4250 (3) | 0.58394 (10) | 0.0306 (3) | |
N3 | 0.25656 (7) | 0.4830 (3) | 0.77298 (10) | 0.0370 (3) | |
N4 | 0.09621 (6) | −0.1206 (3) | 0.62525 (10) | 0.0310 (3) | |
C1 | 0.37153 (7) | 0.8752 (3) | 0.73231 (13) | 0.0347 (3) | |
H1A | 0.3673 | 0.8152 | 0.8086 | 0.042* | |
C2 | 0.42482 (7) | 1.0749 (3) | 0.70784 (14) | 0.0370 (4) | |
H2B | 0.4571 | 1.1525 | 0.7680 | 0.044* | |
C3 | 0.43132 (8) | 1.1617 (3) | 0.59726 (14) | 0.0381 (4) | |
H3B | 0.4684 | 1.2965 | 0.5811 | 0.046* | |
C4 | 0.38356 (8) | 1.0513 (4) | 0.51003 (14) | 0.0405 (4) | |
H4B | 0.3874 | 1.1135 | 0.4339 | 0.049* | |
C5 | 0.33006 (7) | 0.8506 (3) | 0.53232 (13) | 0.0357 (4) | |
H5A | 0.2977 | 0.7737 | 0.4720 | 0.043* | |
C6 | 0.32462 (6) | 0.7647 (3) | 0.64333 (12) | 0.0280 (3) | |
C7 | 0.18671 (7) | 0.2479 (3) | 0.63998 (11) | 0.0288 (3) | |
C8 | 0.20430 (7) | 0.2846 (3) | 0.75709 (12) | 0.0357 (3) | |
H8A | 0.1824 | 0.1840 | 0.8159 | 0.043* | |
C9 | 0.13538 (7) | 0.0576 (3) | 0.57624 (12) | 0.0313 (3) | |
H9A | 0.1311 | 0.0673 | 0.4952 | 0.038* | |
C10 | 0.04894 (7) | −0.3064 (3) | 0.55821 (12) | 0.0277 (3) | |
C11 | 0.05561 (7) | −0.3664 (3) | 0.44302 (12) | 0.0309 (3) | |
H11A | 0.0938 | −0.2770 | 0.4036 | 0.037* | |
C12 | −0.00713 (7) | −0.4452 (3) | 0.61426 (12) | 0.0291 (3) | |
H12A | −0.0120 | −0.4095 | 0.6929 | 0.035* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0292 (5) | 0.0276 (7) | 0.0271 (6) | 0.0006 (4) | 0.0011 (4) | −0.0024 (5) |
N2 | 0.0324 (5) | 0.0279 (7) | 0.0312 (7) | −0.0011 (4) | 0.0000 (4) | −0.0033 (5) |
N3 | 0.0419 (6) | 0.0401 (8) | 0.0293 (7) | −0.0083 (5) | 0.0041 (5) | −0.0032 (5) |
N4 | 0.0298 (5) | 0.0277 (7) | 0.0358 (7) | −0.0014 (4) | 0.0038 (4) | −0.0062 (5) |
C1 | 0.0352 (7) | 0.0353 (8) | 0.0334 (8) | −0.0030 (6) | 0.0005 (5) | −0.0005 (6) |
C2 | 0.0334 (7) | 0.0337 (9) | 0.0433 (9) | −0.0031 (5) | −0.0010 (5) | −0.0044 (6) |
C3 | 0.0348 (7) | 0.0319 (8) | 0.0482 (9) | −0.0032 (6) | 0.0078 (6) | −0.0022 (7) |
C4 | 0.0453 (8) | 0.0402 (10) | 0.0369 (8) | −0.0043 (6) | 0.0084 (6) | 0.0037 (7) |
C5 | 0.0367 (7) | 0.0369 (9) | 0.0333 (8) | −0.0024 (6) | 0.0019 (5) | −0.0023 (6) |
C6 | 0.0258 (6) | 0.0231 (7) | 0.0353 (8) | 0.0028 (5) | 0.0032 (5) | −0.0020 (5) |
C7 | 0.0271 (6) | 0.0249 (7) | 0.0345 (8) | 0.0017 (5) | 0.0032 (5) | −0.0013 (5) |
C8 | 0.0378 (7) | 0.0368 (9) | 0.0331 (8) | −0.0063 (6) | 0.0069 (5) | −0.0026 (6) |
C9 | 0.0341 (7) | 0.0269 (8) | 0.0325 (8) | −0.0005 (5) | 0.0004 (5) | −0.0027 (6) |
C10 | 0.0279 (6) | 0.0229 (7) | 0.0324 (7) | 0.0020 (5) | 0.0022 (5) | −0.0017 (5) |
C11 | 0.0313 (6) | 0.0281 (8) | 0.0339 (8) | −0.0017 (5) | 0.0076 (5) | −0.0013 (6) |
C12 | 0.0341 (6) | 0.0259 (7) | 0.0278 (7) | 0.0016 (5) | 0.0055 (5) | −0.0022 (5) |
N1—N2 | 1.332 (2) | C4—C5 | 1.389 (2) |
N1—N3 | 1.339 (2) | C4—H4B | 0.9500 |
N1—C6 | 1.424 (2) | C5—C6 | 1.379 (2) |
N2—C7 | 1.337 (2) | C5—H5A | 0.9500 |
N3—C8 | 1.329 (2) | C7—C8 | 1.398 (2) |
N4—C9 | 1.267 (2) | C7—C9 | 1.4534 (19) |
N4—C10 | 1.419 (2) | C8—H8A | 0.9500 |
C1—C6 | 1.389 (2) | C9—H9A | 0.9500 |
C1—C2 | 1.389 (2) | C10—C11 | 1.398 (2) |
C1—H1A | 0.9500 | C10—C12 | 1.400 (2) |
C2—C3 | 1.378 (2) | C11—C12i | 1.384 (2) |
C2—H2B | 0.9500 | C11—H11A | 0.9500 |
C3—C4 | 1.382 (2) | C12—C11i | 1.384 (2) |
C3—H3B | 0.9500 | C12—H12A | 0.9500 |
N2—N1—N3 | 115.1 (1) | C5—C6—C1 | 121.1 (1) |
N2—N1—C6 | 122.2 (1) | C5—C6—N1 | 119.2 (1) |
N3—N1—C6 | 122.6 (1) | C1—C6—N1 | 119.7 (1) |
N1—N2—C7 | 103.9 (1) | N2—C7—C8 | 108.3 (1) |
C8—N3—N1 | 103.5 (1) | N2—C7—C9 | 119.7 (1) |
C9—N4—C10 | 119.4 (1) | C8—C7—C9 | 132.0 (1) |
C6—C1—C2 | 118.9 (1) | N3—C8—C7 | 109.1 (1) |
C6—C1—H1A | 120.6 | N3—C8—H8A | 125.4 |
C2—C1—H1A | 120.6 | C7—C8—H8A | 125.4 |
C3—C2—C1 | 120.7 (1) | N4—C9—C7 | 122.1 (1) |
C3—C2—H2B | 119.6 | N4—C9—H9A | 119.0 |
C1—C2—H2B | 119.6 | C7—C9—H9A | 119.0 |
C2—C3—C4 | 119.5 (1) | C11—C10—C12 | 118.3 (1) |
C2—C3—H3B | 120.2 | C11—C10—N4 | 125.3 (1) |
C4—C3—H3B | 120.2 | C12—C10—N4 | 116.5 (1) |
C3—C4—C5 | 120.8 (2) | C12i—C11—C10 | 120.7 (1) |
C3—C4—H4B | 119.6 | C12i—C11—H11A | 119.7 |
C5—C4—H4B | 119.6 | C10—C11—H11A | 119.7 |
C6—C5—C4 | 119.0 (1) | C11i—C12—C10 | 121.1 (1) |
C6—C5—H5A | 120.5 | C11i—C12—H12A | 119.5 |
C4—C5—H5A | 120.5 | C10—C12—H12A | 119.5 |
N3—N1—N2—C7 | −0.15 (14) | N3—N1—C6—C1 | 5.34 (19) |
C6—N1—N2—C7 | 177.84 (11) | N1—N2—C7—C8 | −0.03 (14) |
N2—N1—N3—C8 | 0.26 (16) | N1—N2—C7—C9 | −178.61 (11) |
C6—N1—N3—C8 | −177.72 (12) | N1—N3—C8—C7 | −0.26 (16) |
C6—C1—C2—C3 | −0.2 (2) | N2—C7—C8—N3 | 0.19 (16) |
C1—C2—C3—C4 | 0.9 (2) | C9—C7—C8—N3 | 178.54 (14) |
C2—C3—C4—C5 | −1.1 (2) | C10—N4—C9—C7 | −178.01 (12) |
C3—C4—C5—C6 | 0.7 (2) | N2—C7—C9—N4 | 177.51 (12) |
C4—C5—C6—C1 | 0.0 (2) | C8—C7—C9—N4 | −0.7 (2) |
C4—C5—C6—N1 | 179.65 (12) | C9—N4—C10—C11 | 18.5 (2) |
C2—C1—C6—C5 | −0.2 (2) | C9—N4—C10—C12 | −163.55 (12) |
C2—C1—C6—N1 | −179.90 (12) | C12—C10—C11—C12i | 1.0 (2) |
N2—N1—C6—C5 | 7.83 (18) | N4—C10—C11—C12i | 179.00 (12) |
N3—N1—C6—C5 | −174.33 (12) | C11—C10—C12—C11i | −1.0 (2) |
N2—N1—C6—C1 | −172.50 (12) | N4—C10—C12—C11i | −179.18 (12) |
Symmetry code: (i) −x, −y−1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C24H18N8 |
Mr | 418.46 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 153 |
a, b, c (Å) | 17.670 (4), 4.800 (1), 11.751 (2) |
β (°) | 94.42 (3) |
V (Å3) | 993.7 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.45 × 0.40 × 0.35 |
Data collection | |
Diffractometer | Rigaku R-AXIS SPIDER |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8889, 2273, 1743 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.120, 1.02 |
No. of reflections | 2273 |
No. of parameters | 146 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.24 |
Computer programs: RAPID-AUTO (Rigaku, 2004), RAPID-AUTO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998), WinGX (Farrugia, 1998).
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Aromatic nitrogen heterocycles are arguably the most facile and ligands used widely in coordination chemistry. Ligands based on heterocycles containing more than one nitrogen atom within the aromatic ring are capable of forming oligo- and polynuclear coordination compounds by bridging metal centres (Klingele et al., 2004). Schiff bases are condensation products of arylamines and carbonyl compounds. Unlike the aliphatic imines, these compounds are quite stable and represent versatile intermediates for preparation of a number of industrial and biological compounds, for example, arendiazonium nitrates, N-arylarencarboxamides, corresponding amines and cyanoamines, beta-lactams (Yan et al.,2005). 1,2,3-triazole and its derivatives are important in the synthesis of heteroarmatic compounds.
We report here the crystal structure of (I) (Fig. 1), synthesized by the reaction of 1,4-phenylene diamine with 2-phenyl-1,2,3-triazol-4-carbaldehyde. The bond lengths and angles in the (I), show normal values. In the crystal structure, π—π stacking interactions are observed between adjacent molecules, which is parallel (Fig. 2). The Cg1···Cg2iv distance is 3.485 (2) Å (Cg1 and Cg2 are the centroids of the N1,N2/C7,C8/N3 and C1-C6 rings; symmetry code as in Fig. 2).