


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680802521X/ci2648sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S160053680802521X/ci2648Isup2.hkl |
CCDC reference: 702465
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.005 Å
- R factor = 0.051
- wR factor = 0.095
- Data-to-parameter ratio = 8.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.00 From the CIF: _reflns_number_total 1647 Count of symmetry unique reflns 1660 Completeness (_total/calc) 99.22% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 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 2 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 by the Schiff base condensation of 2-methoxybenzaldehyde (0.1 mol) and 2-methoxybenzohydrazide (0.1 mmol) in ethanol (50 ml). The excess ethanol was removed by distillation. The colorless solid obtained was filtered and washed with ethanol. Single crystals suitable for X-ray diffraction were obatined by slow evaporation of an ethanol solution at room temperature.
The imino H atom was located in a difference map and refined with a N–H distance restraint of 0.90 (1) Å. The other H atoms were positioned geometrically (C–H = 0.93-0.96 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(Cmethyl). In the absence of significant anomalous scattering, Friedel pairs were merged.
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C16H16N2O3 | F(000) = 300 |
Mr = 284.31 | Dx = 1.297 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 744 reflections |
a = 4.9998 (13) Å | θ = 2.5–24.0° |
b = 13.475 (4) Å | µ = 0.09 mm−1 |
c = 10.824 (3) Å | T = 298 K |
β = 93.674 (4)° | Block, colourless |
V = 727.7 (4) Å3 | 0.30 × 0.30 × 0.28 mm |
Z = 2 |
Bruker APEXII CCD area-detector diffractometer | 1647 independent reflections |
Radiation source: fine-focus sealed tube | 1229 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
ω scans | θmax = 27.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −6→6 |
Tmin = 0.973, Tmax = 0.975 | k = −17→16 |
6081 measured reflections | l = −13→13 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0297P)2] where P = (Fo2 + 2Fc2)/3 |
1647 reflections | (Δ/σ)max = 0.001 |
195 parameters | Δρmax = 0.16 e Å−3 |
2 restraints | Δρmin = −0.14 e Å−3 |
C16H16N2O3 | V = 727.7 (4) Å3 |
Mr = 284.31 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 4.9998 (13) Å | µ = 0.09 mm−1 |
b = 13.475 (4) Å | T = 298 K |
c = 10.824 (3) Å | 0.30 × 0.30 × 0.28 mm |
β = 93.674 (4)° |
Bruker APEXII CCD area-detector diffractometer | 1647 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 1229 reflections with I > 2σ(I) |
Tmin = 0.973, Tmax = 0.975 | Rint = 0.055 |
6081 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 2 restraints |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.16 e Å−3 |
1647 reflections | Δρmin = −0.14 e Å−3 |
195 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | 0.4130 (5) | 0.5063 (2) | 1.0258 (2) | 0.0579 (8) | |
O2 | 1.2673 (4) | 0.71624 (19) | 0.6930 (2) | 0.0436 (6) | |
O3 | 0.6361 (5) | 0.7245 (2) | 0.4683 (2) | 0.0513 (6) | |
N1 | 0.8931 (5) | 0.5916 (2) | 0.7771 (2) | 0.0357 (7) | |
N2 | 0.8339 (5) | 0.67811 (19) | 0.7116 (3) | 0.0354 (7) | |
C1 | 0.7337 (7) | 0.4561 (2) | 0.8904 (3) | 0.0371 (9) | |
C2 | 0.5766 (7) | 0.4321 (3) | 0.9892 (3) | 0.0426 (9) | |
C3 | 0.6008 (7) | 0.3398 (3) | 1.0439 (3) | 0.0501 (10) | |
H3 | 0.4953 | 0.3233 | 1.1086 | 0.060* | |
C4 | 0.7794 (8) | 0.2725 (3) | 1.0032 (4) | 0.0549 (11) | |
H4 | 0.7928 | 0.2102 | 1.0400 | 0.066* | |
C5 | 0.9407 (8) | 0.2954 (3) | 0.9081 (4) | 0.0537 (10) | |
H5 | 1.0645 | 0.2498 | 0.8818 | 0.064* | |
C6 | 0.9142 (7) | 0.3876 (3) | 0.8529 (3) | 0.0455 (9) | |
H6 | 1.0216 | 0.4036 | 0.7887 | 0.055* | |
C7 | 0.6996 (7) | 0.5520 (2) | 0.8295 (3) | 0.0377 (8) | |
H7 | 0.5353 | 0.5844 | 0.8291 | 0.045* | |
C8 | 1.0305 (6) | 0.7328 (2) | 0.6674 (3) | 0.0296 (7) | |
C9 | 0.9390 (6) | 0.8198 (2) | 0.5913 (3) | 0.0343 (8) | |
C10 | 0.7391 (6) | 0.8162 (3) | 0.4959 (3) | 0.0358 (8) | |
C11 | 0.6635 (7) | 0.9012 (3) | 0.4321 (3) | 0.0518 (10) | |
H11 | 0.5257 | 0.8990 | 0.3703 | 0.062* | |
C12 | 0.7913 (8) | 0.9890 (3) | 0.4597 (4) | 0.0606 (12) | |
H12 | 0.7384 | 1.0462 | 0.4168 | 0.073* | |
C13 | 0.9946 (8) | 0.9936 (3) | 0.5493 (4) | 0.0617 (12) | |
H13 | 1.0835 | 1.0533 | 0.5659 | 0.074* | |
C14 | 1.0677 (7) | 0.9096 (3) | 0.6151 (4) | 0.0478 (10) | |
H14 | 1.2059 | 0.9131 | 0.6767 | 0.057* | |
C15 | 0.2563 (8) | 0.4878 (4) | 1.1267 (4) | 0.0653 (12) | |
H15A | 0.1495 | 0.4295 | 1.1105 | 0.098* | |
H15B | 0.1410 | 0.5435 | 1.1385 | 0.098* | |
H15C | 0.3714 | 0.4778 | 1.2001 | 0.098* | |
C16 | 0.4372 (8) | 0.7167 (4) | 0.3692 (3) | 0.0712 (12) | |
H16A | 0.2821 | 0.7542 | 0.3885 | 0.107* | |
H16B | 0.3884 | 0.6483 | 0.3573 | 0.107* | |
H16C | 0.5066 | 0.7422 | 0.2949 | 0.107* | |
H2 | 0.662 (3) | 0.696 (3) | 0.696 (3) | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0577 (16) | 0.0581 (19) | 0.0601 (19) | 0.0064 (15) | 0.0196 (15) | 0.0132 (15) |
O2 | 0.0265 (12) | 0.0451 (14) | 0.0586 (14) | 0.0050 (12) | −0.0024 (10) | 0.0062 (13) |
O3 | 0.0604 (15) | 0.0471 (15) | 0.0439 (13) | −0.0052 (14) | −0.0149 (11) | 0.0053 (14) |
N1 | 0.0391 (16) | 0.0318 (15) | 0.0356 (15) | 0.0028 (13) | −0.0030 (13) | 0.0079 (13) |
N2 | 0.0271 (14) | 0.0357 (16) | 0.0428 (16) | 0.0036 (13) | −0.0018 (13) | 0.0124 (13) |
C1 | 0.037 (2) | 0.038 (2) | 0.0354 (19) | −0.0036 (16) | −0.0070 (16) | 0.0053 (16) |
C2 | 0.041 (2) | 0.046 (2) | 0.040 (2) | −0.0060 (18) | −0.0050 (18) | 0.0062 (18) |
C3 | 0.054 (2) | 0.051 (3) | 0.045 (2) | −0.011 (2) | −0.0020 (18) | 0.0176 (19) |
C4 | 0.069 (3) | 0.035 (2) | 0.058 (3) | 0.000 (2) | −0.016 (2) | 0.018 (2) |
C5 | 0.061 (3) | 0.043 (2) | 0.056 (3) | 0.0023 (19) | −0.001 (2) | 0.001 (2) |
C6 | 0.049 (2) | 0.042 (2) | 0.045 (2) | −0.0021 (19) | 0.0002 (18) | 0.0085 (18) |
C7 | 0.0336 (18) | 0.043 (2) | 0.0357 (19) | 0.0002 (16) | −0.0008 (16) | 0.0078 (16) |
C8 | 0.0279 (17) | 0.0279 (18) | 0.0332 (16) | −0.0013 (15) | 0.0026 (13) | −0.0029 (15) |
C9 | 0.0317 (17) | 0.0346 (19) | 0.0377 (18) | 0.0046 (15) | 0.0098 (14) | 0.0017 (16) |
C10 | 0.0368 (19) | 0.0353 (19) | 0.0357 (19) | 0.0037 (16) | 0.0051 (15) | 0.0015 (17) |
C11 | 0.055 (2) | 0.056 (3) | 0.044 (2) | 0.008 (2) | 0.001 (2) | 0.013 (2) |
C12 | 0.065 (3) | 0.046 (3) | 0.071 (3) | 0.007 (2) | 0.009 (2) | 0.027 (2) |
C13 | 0.072 (3) | 0.039 (2) | 0.076 (3) | −0.010 (2) | 0.014 (3) | 0.008 (2) |
C14 | 0.048 (2) | 0.037 (2) | 0.058 (2) | −0.0087 (19) | 0.0060 (19) | 0.003 (2) |
C15 | 0.060 (3) | 0.083 (3) | 0.054 (3) | −0.002 (3) | 0.012 (2) | 0.009 (2) |
C16 | 0.077 (3) | 0.078 (3) | 0.055 (2) | −0.014 (3) | −0.023 (2) | 0.009 (3) |
O1—C2 | 1.367 (4) | C6—H6 | 0.93 |
O1—C15 | 1.407 (4) | C7—H7 | 0.93 |
O2—C8 | 1.220 (3) | C8—C9 | 1.488 (4) |
O3—C10 | 1.364 (4) | C9—C14 | 1.387 (5) |
O3—C16 | 1.419 (4) | C9—C10 | 1.391 (4) |
N1—C7 | 1.270 (4) | C10—C11 | 1.378 (5) |
N1—N2 | 1.387 (3) | C11—C12 | 1.368 (5) |
N2—C8 | 1.341 (4) | C11—H11 | 0.93 |
N2—H2 | 0.901 (10) | C12—C13 | 1.360 (5) |
C1—C6 | 1.370 (5) | C12—H12 | 0.93 |
C1—C2 | 1.405 (5) | C13—C14 | 1.375 (5) |
C1—C7 | 1.456 (4) | C13—H13 | 0.93 |
C2—C3 | 1.380 (5) | C14—H14 | 0.93 |
C3—C4 | 1.365 (5) | C15—H15A | 0.96 |
C3—H3 | 0.93 | C15—H15B | 0.96 |
C4—C5 | 1.383 (5) | C15—H15C | 0.96 |
C4—H4 | 0.93 | C16—H16A | 0.96 |
C5—C6 | 1.381 (5) | C16—H16B | 0.96 |
C5—H5 | 0.93 | C16—H16C | 0.96 |
C2—O1—C15 | 118.0 (3) | C14—C9—C10 | 118.1 (3) |
C10—O3—C16 | 118.0 (3) | C14—C9—C8 | 117.5 (3) |
C7—N1—N2 | 115.9 (3) | C10—C9—C8 | 124.3 (3) |
C8—N2—N1 | 120.5 (2) | O3—C10—C11 | 123.8 (3) |
C8—N2—H2 | 120 (3) | O3—C10—C9 | 115.9 (3) |
N1—N2—H2 | 120 (3) | C11—C10—C9 | 120.3 (3) |
C6—C1—C2 | 118.8 (3) | C12—C11—C10 | 120.0 (4) |
C6—C1—C7 | 121.6 (3) | C12—C11—H11 | 120.0 |
C2—C1—C7 | 119.6 (3) | C10—C11—H11 | 120.0 |
O1—C2—C3 | 125.0 (3) | C13—C12—C11 | 120.8 (4) |
O1—C2—C1 | 115.3 (3) | C13—C12—H12 | 119.6 |
C3—C2—C1 | 119.7 (4) | C11—C12—H12 | 119.6 |
C4—C3—C2 | 120.1 (4) | C12—C13—C14 | 119.6 (4) |
C4—C3—H3 | 120.0 | C12—C13—H13 | 120.2 |
C2—C3—H3 | 119.9 | C14—C13—H13 | 120.2 |
C3—C4—C5 | 121.1 (3) | C13—C14—C9 | 121.2 (4) |
C3—C4—H4 | 119.5 | C13—C14—H14 | 119.4 |
C5—C4—H4 | 119.5 | C9—C14—H14 | 119.4 |
C6—C5—C4 | 118.6 (4) | O1—C15—H15A | 109.5 |
C6—C5—H5 | 120.7 | O1—C15—H15B | 109.5 |
C4—C5—H5 | 120.7 | H15A—C15—H15B | 109.5 |
C1—C6—C5 | 121.6 (4) | O1—C15—H15C | 109.5 |
C1—C6—H6 | 119.2 | H15A—C15—H15C | 109.5 |
C5—C6—H6 | 119.2 | H15B—C15—H15C | 109.5 |
N1—C7—C1 | 120.3 (3) | O3—C16—H16A | 109.5 |
N1—C7—H7 | 119.9 | O3—C16—H16B | 109.5 |
C1—C7—H7 | 119.9 | H16A—C16—H16B | 109.5 |
O2—C8—N2 | 122.8 (3) | O3—C16—H16C | 109.5 |
O2—C8—C9 | 122.0 (3) | H16A—C16—H16C | 109.5 |
N2—C8—C9 | 115.1 (3) | H16B—C16—H16C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2i | 0.90 (1) | 1.99 (1) | 2.873 (3) | 167 (4) |
Symmetry code: (i) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C16H16N2O3 |
Mr | 284.31 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 298 |
a, b, c (Å) | 4.9998 (13), 13.475 (4), 10.824 (3) |
β (°) | 93.674 (4) |
V (Å3) | 727.7 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.30 × 0.28 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.973, 0.975 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6081, 1647, 1229 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.095, 1.11 |
No. of reflections | 1647 |
No. of parameters | 195 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.16, −0.14 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2i | 0.90 (1) | 1.99 (1) | 2.873 (3) | 167 (4) |
Symmetry code: (i) x−1, y, z. |
As part of our investigation of the crystal structures of Schiff bases derived from the condensation of aldehydes with benzohydrazides (Lu et al., 2008a,b), we report here the crystal structure of the title new Schiff base compound.
In the title molecule (Fig. 1). the bond lengths have normal values (Allen et al., 1987), and are comparable to those observed in related compounds (Nie, 2008; He, 2008; Shi et al., 2007). The dihedral angle between the two aromatic rings is 87.5 (3)°, indicating that they are almost perpendicular to one another.
In the crystal structure, the molecules are linked into chains (Fig. 2) running parallel to the a axis by intermolecular N–H···O hydrogen bonds (Table 1).