Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051707/xu2335sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051707/xu2335Isup2.hkl |
CCDC reference: 667447
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.041
- wR factor = 0.094
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT148_ALERT_3_B su on the a - Axis is Too Large (x 1000) . 20 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Jiang & Hu (2004); Kundu et al. (2005); Trujillo et al. (1997); Zheng & Zhao (2006); Zhao et al. (2006).
The title compound was prepared by the reaction of hydrocinncmaladehyde and hydrazine hydrate with a ratio of 2:1 under reflux in the mixture of ethanol and DMF for 2 h. After one week, yellow prismatic crystals were obtained by slow evaporation at room temperature.
All H atoms were placed in calculated positions and treated using a riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).
The azine derivatives have been investigated in terms of their coordination chemistry and their special properties (Zheng & Zhao, 2006; Kundu et al., 2005; Jiang & Hu, 2004; Trujillo et al., 1997). The synthesis and crystal structure of the title compound (Fig. 1) is reported here.
In the molecule of title molecule, there is an inversion center at the midpoint of the N1—N1A single bond [symmetry code A, -x, -y, -z + 1], and all of the atoms are approximately coplanar. The single N—N bond length is 1.398 (3) Å (Table 1), which is consistent with those found in related azine compounds (Zheng & Zhao, 2006; Zhao et al., 2006). The bond angle of N(1)—C(9)—C(8) is 120.9 (2)°, showing the atom C9 is of sp2 hybridization.
For related literature, see: Jiang & Hu (2004); Kundu et al. (2005); Trujillo et al. (1997); Zheng & Zhao (2006); Zhao et al. (2006).
Data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY (Molecular Structure Corporation, 1999); data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. View of the molecular structure with displacement ellipsoids drawn at the 30% probability level for non-H atoms. [Symmetry code: (A) -x, -y, -z + 1.] |
C18H16N2 | F(000) = 276 |
Mr = 260.33 | Dx = 1.172 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1381 reflections |
a = 17.11 (2) Å | θ = 3.6–26.0° |
b = 5.456 (5) Å | µ = 0.07 mm−1 |
c = 7.988 (7) Å | T = 293 K |
β = 98.25 (4)° | Prism, yellow |
V = 738.0 (13) Å3 | 0.55 × 0.21 × 0.12 mm |
Z = 2 |
Rigaku R-AXIS RAPID IP diffractometer | 844 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 26.0°, θmin = 3.6° |
ω scans | h = −21→21 |
5393 measured reflections | k = −6→6 |
1381 independent reflections | l = −9→9 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0491P)2] where P = (Fo2 + 2Fc2)/3 |
1381 reflections | (Δ/σ)max < 0.001 |
91 parameters | Δρmax = 0.09 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
C18H16N2 | V = 738.0 (13) Å3 |
Mr = 260.33 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 17.11 (2) Å | µ = 0.07 mm−1 |
b = 5.456 (5) Å | T = 293 K |
c = 7.988 (7) Å | 0.55 × 0.21 × 0.12 mm |
β = 98.25 (4)° |
Rigaku R-AXIS RAPID IP diffractometer | 844 reflections with I > 2σ(I) |
5393 measured reflections | Rint = 0.034 |
1381 independent reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 0.95 | Δρmax = 0.09 e Å−3 |
1381 reflections | Δρmin = −0.14 e Å−3 |
91 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 | 0.04070 (6) | −0.0045 (3) | 0.49829 (15) | 0.0722 (4) | |
C1 | 0.26140 (7) | 0.4619 (2) | 0.34602 (14) | 0.0481 (3) | |
C2 | 0.32091 (8) | 0.3004 (2) | 0.41067 (17) | 0.0517 (4) | |
H2A | 0.3085 | 0.1627 | 0.4701 | 0.062* | |
C3 | 0.39765 (8) | 0.3412 (3) | 0.38813 (17) | 0.0568 (4) | |
H3A | 0.4367 | 0.2307 | 0.4321 | 0.068* | |
C4 | 0.41760 (9) | 0.5435 (3) | 0.30128 (17) | 0.0608 (4) | |
H4A | 0.4698 | 0.5701 | 0.2863 | 0.073* | |
C5 | 0.35992 (9) | 0.7059 (3) | 0.23671 (19) | 0.0626 (4) | |
H5A | 0.3731 | 0.8428 | 0.1773 | 0.075* | |
C6 | 0.28275 (8) | 0.6675 (3) | 0.25939 (16) | 0.0562 (4) | |
H6A | 0.2443 | 0.7802 | 0.2164 | 0.067* | |
C7 | 0.17886 (8) | 0.4207 (3) | 0.36486 (16) | 0.0579 (4) | |
H7A | 0.1439 | 0.5477 | 0.3309 | 0.070* | |
C8 | 0.14843 (8) | 0.2210 (3) | 0.42545 (18) | 0.0609 (4) | |
H8A | 0.1825 | 0.0927 | 0.4619 | 0.073* | |
C9 | 0.06635 (8) | 0.1918 (3) | 0.43782 (18) | 0.0657 (4) | |
H9A | 0.0312 | 0.3173 | 0.4014 | 0.079* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0402 (6) | 0.0995 (10) | 0.0762 (8) | −0.0123 (7) | 0.0061 (6) | 0.0094 (8) |
C1 | 0.0463 (8) | 0.0529 (8) | 0.0449 (7) | −0.0053 (6) | 0.0062 (5) | −0.0037 (7) |
C2 | 0.0490 (8) | 0.0503 (8) | 0.0561 (8) | −0.0049 (6) | 0.0086 (6) | 0.0018 (7) |
C3 | 0.0481 (8) | 0.0587 (9) | 0.0638 (9) | 0.0000 (7) | 0.0090 (6) | −0.0045 (7) |
C4 | 0.0531 (9) | 0.0677 (11) | 0.0644 (9) | −0.0145 (8) | 0.0178 (7) | −0.0093 (8) |
C5 | 0.0723 (11) | 0.0556 (9) | 0.0622 (9) | −0.0185 (8) | 0.0178 (8) | 0.0014 (7) |
C6 | 0.0616 (9) | 0.0504 (9) | 0.0561 (8) | −0.0006 (7) | 0.0064 (7) | 0.0009 (7) |
C7 | 0.0467 (8) | 0.0688 (10) | 0.0573 (8) | 0.0001 (7) | 0.0039 (6) | 0.0010 (8) |
C8 | 0.0433 (9) | 0.0803 (11) | 0.0588 (9) | −0.0071 (7) | 0.0059 (6) | 0.0042 (8) |
C9 | 0.0456 (9) | 0.0900 (12) | 0.0606 (9) | −0.0084 (8) | 0.0042 (6) | 0.0028 (9) |
N1—C9 | 1.278 (2) | C4—H4A | 0.9300 |
N1—N1i | 1.398 (3) | C5—C6 | 1.374 (2) |
C1—C2 | 1.389 (2) | C5—H5A | 0.9300 |
C1—C6 | 1.3944 (19) | C6—H6A | 0.9300 |
C1—C7 | 1.459 (2) | C7—C8 | 1.329 (2) |
C2—C3 | 1.369 (2) | C7—H7A | 0.9300 |
C2—H2A | 0.9300 | C8—C9 | 1.431 (2) |
C3—C4 | 1.373 (2) | C8—H8A | 0.9300 |
C3—H3A | 0.9300 | C9—H9A | 0.9300 |
C4—C5 | 1.371 (2) | ||
C9—N1—N1i | 112.04 (17) | C4—C5—H5A | 119.8 |
C2—C1—C6 | 117.70 (14) | C6—C5—H5A | 119.8 |
C2—C1—C7 | 122.21 (14) | C5—C6—C1 | 120.87 (14) |
C6—C1—C7 | 120.09 (13) | C5—C6—H6A | 119.6 |
C3—C2—C1 | 120.92 (14) | C1—C6—H6A | 119.6 |
C3—C2—H2A | 119.5 | C8—C7—C1 | 126.82 (14) |
C1—C2—H2A | 119.5 | C8—C7—H7A | 116.6 |
C2—C3—C4 | 120.66 (14) | C1—C7—H7A | 116.6 |
C2—C3—H3A | 119.7 | C7—C8—C9 | 123.78 (15) |
C4—C3—H3A | 119.7 | C7—C8—H8A | 118.1 |
C5—C4—C3 | 119.49 (15) | C9—C8—H8A | 118.1 |
C5—C4—H4A | 120.3 | N1—C9—C8 | 120.86 (16) |
C3—C4—H4A | 120.3 | N1—C9—H9A | 119.6 |
C4—C5—C6 | 120.34 (15) | C8—C9—H9A | 119.6 |
C6—C1—C2—C3 | −0.73 (18) | C7—C1—C6—C5 | −178.33 (12) |
C7—C1—C2—C3 | 178.68 (12) | C2—C1—C7—C8 | −8.1 (2) |
C1—C2—C3—C4 | 0.2 (2) | C6—C1—C7—C8 | 171.33 (13) |
C2—C3—C4—C5 | 0.0 (2) | C1—C7—C8—C9 | −178.97 (12) |
C3—C4—C5—C6 | 0.3 (2) | N1i—N1—C9—C8 | 179.17 (13) |
C4—C5—C6—C1 | −0.9 (2) | C7—C8—C9—N1 | −179.57 (14) |
C2—C1—C6—C5 | 1.08 (19) |
Symmetry code: (i) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C18H16N2 |
Mr | 260.33 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 17.11 (2), 5.456 (5), 7.988 (7) |
β (°) | 98.25 (4) |
V (Å3) | 738.0 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.55 × 0.21 × 0.12 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID IP |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5393, 1381, 844 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.094, 0.95 |
No. of reflections | 1381 |
No. of parameters | 91 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.09, −0.14 |
Computer programs: TEXRAY (Molecular Structure Corporation, 1999), TEXSAN (Molecular Structure Corporation, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEX (McArdle, 1995).
N1—C9 | 1.278 (2) | C7—C8 | 1.329 (2) |
N1—N1i | 1.398 (3) | ||
C9—N1—N1i | 112.04 (17) | ||
N1i—N1—C9—C8 | 179.17 (13) |
Symmetry code: (i) −x, −y, −z+1. |
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The azine derivatives have been investigated in terms of their coordination chemistry and their special properties (Zheng & Zhao, 2006; Kundu et al., 2005; Jiang & Hu, 2004; Trujillo et al., 1997). The synthesis and crystal structure of the title compound (Fig. 1) is reported here.
In the molecule of title molecule, there is an inversion center at the midpoint of the N1—N1A single bond [symmetry code A, -x, -y, -z + 1], and all of the atoms are approximately coplanar. The single N—N bond length is 1.398 (3) Å (Table 1), which is consistent with those found in related azine compounds (Zheng & Zhao, 2006; Zhao et al., 2006). The bond angle of N(1)—C(9)—C(8) is 120.9 (2)°, showing the atom C9 is of sp2 hybridization.