Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048350/sg2194sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048350/sg2194Isup2.hkl |
CCDC reference: 667300
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.060
- wR factor = 0.159
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
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 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Ali et al. (2002); Allen et al. (1987); Cukurovali et al. (2002); Li (2007); Qian et al. (2006); Qiu et al. (2006); Tarafder et al. (2002); Yang (2006); Yang & Guo (2006); Zhao (2006).
3-Methoxysalicylaldehyde (0.1 mmol, 15.2 mg) and 4-methylpyridin-2-ylamine (0.1 mmol, 10.8 mg) were dissolved in methanol (10 ml). The mixture was stirred at room temperature for 10 min to give a clear yellow solution. Crystals of (I) were formed by gradual evaporation of the solvent over a week at room temperature (yield 87.2%).
H atoms were placed in geometrically idealized positions and allowed to ride on their parent atoms, with O—H = 0.82 Å, C—H = 0.93–0.96 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl,O).
The compounds derived from the condensation reaction of aromatic carbaldehydes with hydrazides exhibit a wide range of biological activities and applications (Tarafder et al., 2002; Cukurovali et al., 2002; Ali et al., 2002). Recently, the author has reported a Schiff base compound (Li, 2007). As a further investigation, the author reports here the crystal structure of the new Schiff base compound, Fig. 1.
All the bond lengths and angles are within normal ranges (Allen et al., 1987) and comparable with those observed in similar compounds (Qiu et al., 2006; Yang and Guo, 2006; Yang, 2006). The C8═N1 bond length of 1.285 (3) Å conforms to the value for a double bond, and is comparable with that in other Schiff bases (Qian et al., 2006; Zhao, 2006). The molecule displays an E configuration about the C═N double bond. The dihedral angle between the benzene ring and the pyridine ring is 5.4 (2)°.
The molecular structure is stablized by weak πi-πi interactions, stacking along the b axis (Fig. 2).
For related literature, see: Ali et al. (2002); Allen et al. (1987); Cukurovali et al. (2002); Li (2007); Qian et al. (2006); Qiu et al. (2006); Tarafder et al. (2002); Yang (2006); Yang & Guo (2006); Zhao (2006).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
C14H14N2O2 | F(000) = 512 |
Mr = 242.27 | Dx = 1.333 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 713 reflections |
a = 9.997 (2) Å | θ = 2.5–24.5° |
b = 4.896 (1) Å | µ = 0.09 mm−1 |
c = 24.729 (5) Å | T = 298 K |
β = 94.24 (3)° | Block, yellow |
V = 1207.1 (4) Å3 | 0.23 × 0.20 × 0.20 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2498 independent reflections |
Radiation source: fine-focus sealed tube | 1384 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
ω scans | θmax = 26.5°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.979, Tmax = 0.982 | k = −6→6 |
8333 measured reflections | l = −30→31 |
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)] = 0.060 | H-atom parameters constrained |
wR(F2) = 0.159 | w = 1/[σ2(Fo2) + (0.0322P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2498 reflections | Δρmax = 0.18 e Å−3 |
167 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.011 (3) |
C14H14N2O2 | V = 1207.1 (4) Å3 |
Mr = 242.27 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.997 (2) Å | µ = 0.09 mm−1 |
b = 4.896 (1) Å | T = 298 K |
c = 24.729 (5) Å | 0.23 × 0.20 × 0.20 mm |
β = 94.24 (3)° |
Bruker SMART CCD area-detector diffractometer | 2498 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1384 reflections with I > 2σ(I) |
Tmin = 0.979, Tmax = 0.982 | Rint = 0.060 |
8333 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.18 e Å−3 |
2498 reflections | Δρmin = −0.18 e Å−3 |
167 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 | 0.25493 (18) | 0.8248 (4) | 0.07335 (7) | 0.0551 (6) | |
H1 | 0.1972 | 0.9383 | 0.0789 | 0.083* | |
O2 | 0.44898 (18) | 0.4723 (4) | 0.07002 (7) | 0.0585 (6) | |
N1 | 0.08363 (19) | 1.0839 (4) | 0.12784 (8) | 0.0442 (5) | |
N2 | −0.0684 (2) | 1.3400 (4) | 0.17759 (8) | 0.0516 (6) | |
C1 | 0.2269 (2) | 0.7364 (5) | 0.16759 (10) | 0.0407 (6) | |
C2 | 0.2902 (2) | 0.6903 (5) | 0.11964 (10) | 0.0403 (6) | |
C3 | 0.3939 (2) | 0.4971 (5) | 0.11899 (10) | 0.0438 (6) | |
C4 | 0.4341 (2) | 0.3547 (5) | 0.16547 (11) | 0.0491 (7) | |
H4 | 0.5037 | 0.2288 | 0.1651 | 0.059* | |
C5 | 0.3704 (3) | 0.3993 (5) | 0.21317 (11) | 0.0507 (7) | |
H5 | 0.3974 | 0.3022 | 0.2444 | 0.061* | |
C6 | 0.2682 (3) | 0.5856 (5) | 0.21406 (10) | 0.0477 (7) | |
H6 | 0.2259 | 0.6124 | 0.2459 | 0.057* | |
C7 | 0.5342 (3) | 0.2432 (5) | 0.06291 (11) | 0.0584 (8) | |
H7A | 0.6101 | 0.2514 | 0.0890 | 0.088* | |
H7B | 0.5645 | 0.2463 | 0.0270 | 0.088* | |
H7C | 0.4852 | 0.0775 | 0.0680 | 0.088* | |
C8 | 0.1211 (2) | 0.9378 (5) | 0.16942 (10) | 0.0425 (6) | |
H8 | 0.0793 | 0.9619 | 0.2014 | 0.051* | |
C9 | −0.0183 (2) | 1.2843 (5) | 0.13012 (10) | 0.0412 (6) | |
C10 | −0.0592 (2) | 1.4159 (5) | 0.08256 (10) | 0.0461 (7) | |
H10 | −0.0199 | 1.3710 | 0.0508 | 0.055* | |
C11 | −0.1581 (2) | 1.6146 (5) | 0.08139 (10) | 0.0457 (7) | |
C12 | −0.2092 (2) | 1.6755 (5) | 0.13031 (11) | 0.0499 (7) | |
H12 | −0.2747 | 1.8093 | 0.1322 | 0.060* | |
C13 | −0.1623 (3) | 1.5363 (6) | 0.17616 (11) | 0.0573 (8) | |
H13 | −0.1983 | 1.5816 | 0.2086 | 0.069* | |
C14 | −0.2051 (3) | 1.7581 (7) | 0.02971 (12) | 0.0704 (9) | |
H14A | −0.2917 | 1.8374 | 0.0335 | 0.106* | |
H14B | −0.2112 | 1.6291 | 0.0004 | 0.106* | |
H14C | −0.1425 | 1.8993 | 0.0222 | 0.106* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0617 (13) | 0.0558 (13) | 0.0489 (11) | 0.0195 (9) | 0.0112 (9) | 0.0103 (9) |
O2 | 0.0626 (12) | 0.0599 (13) | 0.0553 (12) | 0.0237 (9) | 0.0197 (9) | 0.0067 (10) |
N1 | 0.0431 (12) | 0.0400 (13) | 0.0496 (13) | 0.0046 (10) | 0.0053 (10) | −0.0023 (11) |
N2 | 0.0548 (14) | 0.0528 (15) | 0.0484 (14) | 0.0104 (11) | 0.0119 (11) | −0.0016 (11) |
C1 | 0.0368 (14) | 0.0387 (15) | 0.0464 (15) | −0.0021 (11) | 0.0034 (11) | −0.0036 (12) |
C2 | 0.0432 (14) | 0.0378 (14) | 0.0398 (15) | 0.0001 (11) | 0.0029 (11) | 0.0051 (12) |
C3 | 0.0429 (14) | 0.0427 (15) | 0.0466 (16) | 0.0021 (12) | 0.0086 (12) | −0.0010 (13) |
C4 | 0.0410 (15) | 0.0468 (17) | 0.0596 (18) | 0.0061 (12) | 0.0054 (13) | 0.0024 (14) |
C5 | 0.0584 (17) | 0.0435 (16) | 0.0495 (17) | 0.0023 (13) | 0.0004 (13) | 0.0086 (13) |
C6 | 0.0543 (17) | 0.0463 (16) | 0.0431 (15) | 0.0034 (13) | 0.0080 (12) | −0.0010 (13) |
C7 | 0.0523 (16) | 0.0560 (19) | 0.069 (2) | 0.0111 (14) | 0.0191 (14) | −0.0042 (15) |
C8 | 0.0429 (15) | 0.0392 (15) | 0.0460 (15) | −0.0031 (12) | 0.0077 (12) | −0.0049 (12) |
C9 | 0.0391 (14) | 0.0365 (15) | 0.0486 (16) | −0.0014 (11) | 0.0072 (12) | −0.0047 (12) |
C10 | 0.0470 (16) | 0.0480 (17) | 0.0442 (16) | 0.0034 (12) | 0.0102 (12) | −0.0052 (13) |
C11 | 0.0437 (15) | 0.0463 (16) | 0.0472 (16) | 0.0036 (12) | 0.0030 (12) | −0.0024 (13) |
C12 | 0.0458 (15) | 0.0444 (16) | 0.0601 (18) | 0.0102 (12) | 0.0082 (13) | −0.0010 (14) |
C13 | 0.0637 (18) | 0.0569 (19) | 0.0536 (18) | 0.0143 (15) | 0.0205 (14) | −0.0019 (15) |
C14 | 0.078 (2) | 0.075 (2) | 0.058 (2) | 0.0247 (17) | 0.0031 (15) | 0.0046 (16) |
O1—C2 | 1.345 (3) | C6—H6 | 0.9300 |
O1—H1 | 0.8200 | C7—H7A | 0.9600 |
O2—C3 | 1.372 (3) | C7—H7B | 0.9600 |
O2—C7 | 1.427 (3) | C7—H7C | 0.9600 |
N1—C8 | 1.285 (3) | C8—H8 | 0.9300 |
N1—C9 | 1.419 (3) | C9—C10 | 1.376 (3) |
N2—C9 | 1.338 (3) | C10—C11 | 1.386 (3) |
N2—C13 | 1.342 (3) | C10—H10 | 0.9300 |
C1—C6 | 1.402 (3) | C11—C12 | 1.380 (3) |
C1—C2 | 1.403 (3) | C11—C14 | 1.503 (4) |
C1—C8 | 1.449 (3) | C12—C13 | 1.375 (3) |
C2—C3 | 1.404 (3) | C12—H12 | 0.9300 |
C3—C4 | 1.379 (3) | C13—H13 | 0.9300 |
C4—C5 | 1.399 (3) | C14—H14A | 0.9600 |
C4—H4 | 0.9300 | C14—H14B | 0.9600 |
C5—C6 | 1.370 (3) | C14—H14C | 0.9600 |
C5—H5 | 0.9300 | ||
C2—O1—H1 | 109.5 | H7A—C7—H7C | 109.5 |
C3—O2—C7 | 117.4 (2) | H7B—C7—H7C | 109.5 |
C8—N1—C9 | 121.4 (2) | N1—C8—C1 | 121.6 (2) |
C9—N2—C13 | 115.4 (2) | N1—C8—H8 | 119.2 |
C6—C1—C2 | 118.9 (2) | C1—C8—H8 | 119.2 |
C6—C1—C8 | 120.3 (2) | N2—C9—C10 | 123.2 (2) |
C2—C1—C8 | 120.8 (2) | N2—C9—N1 | 119.5 (2) |
O1—C2—C1 | 122.3 (2) | C10—C9—N1 | 117.3 (2) |
O1—C2—C3 | 117.9 (2) | C9—C10—C11 | 120.9 (2) |
C1—C2—C3 | 119.9 (2) | C9—C10—H10 | 119.6 |
O2—C3—C4 | 125.4 (2) | C11—C10—H10 | 119.6 |
O2—C3—C2 | 114.5 (2) | C12—C11—C10 | 116.3 (2) |
C4—C3—C2 | 120.1 (2) | C12—C11—C14 | 122.1 (2) |
C3—C4—C5 | 120.0 (2) | C10—C11—C14 | 121.6 (2) |
C3—C4—H4 | 120.0 | C13—C12—C11 | 119.4 (2) |
C5—C4—H4 | 120.0 | C13—C12—H12 | 120.3 |
C6—C5—C4 | 120.3 (2) | C11—C12—H12 | 120.3 |
C6—C5—H5 | 119.9 | N2—C13—C12 | 124.9 (2) |
C4—C5—H5 | 119.9 | N2—C13—H13 | 117.6 |
C5—C6—C1 | 120.8 (2) | C12—C13—H13 | 117.6 |
C5—C6—H6 | 119.6 | C11—C14—H14A | 109.5 |
C1—C6—H6 | 119.6 | C11—C14—H14B | 109.5 |
O2—C7—H7A | 109.5 | H14A—C14—H14B | 109.5 |
O2—C7—H7B | 109.5 | C11—C14—H14C | 109.5 |
H7A—C7—H7B | 109.5 | H14A—C14—H14C | 109.5 |
O2—C7—H7C | 109.5 | H14B—C14—H14C | 109.5 |
Experimental details
Crystal data | |
Chemical formula | C14H14N2O2 |
Mr | 242.27 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 9.997 (2), 4.896 (1), 24.729 (5) |
β (°) | 94.24 (3) |
V (Å3) | 1207.1 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.23 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.979, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8333, 2498, 1384 |
Rint | 0.060 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.159, 1.03 |
No. of reflections | 2498 |
No. of parameters | 167 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.18 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
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The compounds derived from the condensation reaction of aromatic carbaldehydes with hydrazides exhibit a wide range of biological activities and applications (Tarafder et al., 2002; Cukurovali et al., 2002; Ali et al., 2002). Recently, the author has reported a Schiff base compound (Li, 2007). As a further investigation, the author reports here the crystal structure of the new Schiff base compound, Fig. 1.
All the bond lengths and angles are within normal ranges (Allen et al., 1987) and comparable with those observed in similar compounds (Qiu et al., 2006; Yang and Guo, 2006; Yang, 2006). The C8═N1 bond length of 1.285 (3) Å conforms to the value for a double bond, and is comparable with that in other Schiff bases (Qian et al., 2006; Zhao, 2006). The molecule displays an E configuration about the C═N double bond. The dihedral angle between the benzene ring and the pyridine ring is 5.4 (2)°.
The molecular structure is stablized by weak πi-πi interactions, stacking along the b axis (Fig. 2).