Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037014/wn2180sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037014/wn2180Isup2.hkl |
CCDC reference: 660184
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.049
- wR factor = 0.166
- Data-to-parameter ratio = 16.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 3.00 Sigma
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
The reagents were commercial products and were used without further purification. 3-Hydroxy-4-methoxybenzaldehyde (0.1 mmol, 15.2 mg) and 2-hydroxybenzhydrazide (0.1 mmol, 15.2 mg) were dissolved in ethanol (15 ml). The reaction mixture was stirred for 30 minutes to give a clear solution. After allowing the resulting clear solution to stand at room temperature in air for 9 d, large colourless crystals were formed at the bottom of the vessel on slow evaporation of the solvent. The crystals were isolated, washed three times with ethanol and dried in a vacuum desiccator using anhydrous CaCl2 (yield 66%).
Atom H2, attached to O1, was located in a difference Fourier map and refined with an O—H distance restraint of 1.00 (2) Å. The other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H, N—H and O—H, distances of 0.93–0.96, 0.86 and 0.82 Å, respectively. and with Uiso(H) = 1.2Ueq(Csp2, N) or 1.5Ueq(methyl C, O).
Recently, we have reported a few Schiff base complexes (Qiu, Luo et al., 2006; Qiu, Fang et al., 2006), As an extension of our work on the structural characterization of Schiff base compounds, the crystal structure of the title compound is reported here.
In the title compound, all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). The C8═N2 bond length of 1.275 (2) Å conforms to the value for a double bond. The bond length of 1.337 (2) Å between N1 and C7 is greater than the value for a double bond, and less than the value for a single bond, because of conjugation in the molecule. The dihedral angle between the two rings is 3.7 (2)°.
The crystal structure is stabilized by intermolecular O—H···O and N—H···O hydrogen bonds. (Table 1 and Fig. 2)
For related literature, see: Allen et al. (1987); Qiu, Fang, Liu & Zhu (2006); Qiu, Luo, Yang & Liu (2006).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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.
C15H14N2O4 | F(000) = 600 |
Mr = 286.28 | Dx = 1.446 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2865 reflections |
a = 12.436 (3) Å | θ = 4.2–26° |
b = 7.1581 (14) Å | µ = 0.11 mm−1 |
c = 15.048 (3) Å | T = 298 K |
β = 100.95 (3)° | Block, colourless |
V = 1315.2 (5) Å3 | 0.34 × 0.15 × 0.06 mm |
Z = 4 |
Bruker SMART APEX area-detector diffractometer | 3288 independent reflections |
Radiation source: fine-focus sealed tube | 2008 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω scans | θmax = 28.5°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→16 |
Tmin = 0.96, Tmax = 0.99 | k = −9→9 |
11560 measured reflections | l = −19→20 |
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)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.166 | w = 1/[σ2(Fo2) + (0.0815P)2 + 0.0205P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
3288 reflections | Δρmax = 0.28 e Å−3 |
196 parameters | Δρmin = −0.26 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: 0.009 (3) |
C15H14N2O4 | V = 1315.2 (5) Å3 |
Mr = 286.28 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.436 (3) Å | µ = 0.11 mm−1 |
b = 7.1581 (14) Å | T = 298 K |
c = 15.048 (3) Å | 0.34 × 0.15 × 0.06 mm |
β = 100.95 (3)° |
Bruker SMART APEX area-detector diffractometer | 3288 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2008 reflections with I > 2σ(I) |
Tmin = 0.96, Tmax = 0.99 | Rint = 0.030 |
11560 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.166 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.28 e Å−3 |
3288 reflections | Δρmin = −0.26 e Å−3 |
196 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 | ||
C1 | 1.19143 (13) | 0.11923 (19) | 0.43668 (9) | 0.0383 (3) | |
C2 | 1.30560 (13) | 0.1048 (2) | 0.46186 (11) | 0.0455 (4) | |
C3 | 1.35507 (15) | 0.1122 (2) | 0.55284 (12) | 0.0585 (5) | |
H3 | 1.4308 | 0.1022 | 0.5695 | 0.070* | |
C4 | 1.29249 (16) | 0.1342 (2) | 0.61828 (12) | 0.0569 (5) | |
H4 | 1.3266 | 0.1396 | 0.6788 | 0.068* | |
C5 | 1.18013 (14) | 0.1484 (2) | 0.59570 (10) | 0.0482 (4) | |
H5 | 1.1384 | 0.1631 | 0.6404 | 0.058* | |
C6 | 1.13091 (13) | 0.1405 (2) | 0.50587 (10) | 0.0426 (4) | |
H6 | 1.0551 | 0.1496 | 0.4904 | 0.051* | |
C7 | 1.13998 (13) | 0.10751 (19) | 0.34001 (9) | 0.0396 (4) | |
C8 | 0.87839 (12) | 0.1348 (2) | 0.20923 (9) | 0.0408 (4) | |
H8 | 0.8400 | 0.1461 | 0.2563 | 0.049* | |
C9 | 0.81933 (12) | 0.12816 (19) | 0.11589 (9) | 0.0384 (3) | |
C10 | 0.87688 (12) | 0.11754 (19) | 0.04428 (9) | 0.0382 (3) | |
H10 | 0.9530 | 0.1131 | 0.0567 | 0.046* | |
C11 | 0.82212 (12) | 0.11374 (19) | −0.04359 (9) | 0.0364 (3) | |
C12 | 0.70753 (13) | 0.1193 (2) | −0.06330 (10) | 0.0423 (4) | |
C13 | 0.64983 (13) | 0.1286 (2) | 0.00710 (11) | 0.0511 (4) | |
H13 | 0.5737 | 0.1317 | −0.0054 | 0.061* | |
C14 | 0.70586 (13) | 0.1333 (2) | 0.09602 (11) | 0.0470 (4) | |
H14 | 0.6668 | 0.1400 | 0.1429 | 0.056* | |
C21 | 0.54812 (16) | 0.1023 (3) | −0.17878 (14) | 0.0823 (7) | |
H21A | 0.5231 | −0.0063 | −0.1512 | 0.123* | |
H21B | 0.5280 | 0.0921 | −0.2434 | 0.123* | |
H21C | 0.5150 | 0.2119 | −0.1589 | 0.123* | |
H2 | 1.3208 (19) | 0.093 (3) | 0.3393 (15) | 0.084 (7)* | |
N1 | 1.03213 (10) | 0.13674 (18) | 0.31683 (8) | 0.0444 (3) | |
H1 | 0.9941 | 0.1624 | 0.3574 | 0.053* | |
N2 | 0.98266 (11) | 0.12502 (17) | 0.22650 (8) | 0.0448 (4) | |
O1 | 1.37067 (10) | 0.08214 (18) | 0.39977 (9) | 0.0628 (4) | |
O2 | 1.19532 (9) | 0.06595 (17) | 0.28146 (7) | 0.0521 (3) | |
O3 | 0.88194 (8) | 0.10779 (14) | −0.11127 (7) | 0.0461 (3) | |
H11 | 0.8403 | 0.1059 | −0.1605 | 0.069* | |
O4 | 0.66287 (9) | 0.11568 (16) | −0.15360 (7) | 0.0558 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0423 (8) | 0.0413 (8) | 0.0314 (7) | 0.0009 (6) | 0.0073 (6) | 0.0002 (6) |
C2 | 0.0432 (9) | 0.0495 (9) | 0.0437 (9) | −0.0010 (7) | 0.0083 (7) | 0.0026 (6) |
C3 | 0.0445 (10) | 0.0752 (12) | 0.0513 (10) | −0.0006 (8) | −0.0020 (8) | 0.0011 (8) |
C4 | 0.0639 (12) | 0.0638 (11) | 0.0377 (9) | −0.0005 (8) | −0.0035 (8) | 0.0007 (7) |
C5 | 0.0609 (10) | 0.0502 (9) | 0.0336 (8) | 0.0018 (7) | 0.0096 (7) | −0.0002 (6) |
C6 | 0.0441 (8) | 0.0483 (9) | 0.0357 (8) | 0.0017 (6) | 0.0080 (6) | −0.0003 (6) |
C7 | 0.0433 (8) | 0.0446 (8) | 0.0323 (8) | 0.0014 (6) | 0.0107 (6) | 0.0015 (6) |
C8 | 0.0440 (9) | 0.0489 (9) | 0.0311 (7) | −0.0006 (6) | 0.0112 (6) | −0.0023 (6) |
C9 | 0.0423 (8) | 0.0425 (8) | 0.0315 (7) | −0.0020 (6) | 0.0094 (6) | −0.0020 (6) |
C10 | 0.0352 (8) | 0.0453 (8) | 0.0343 (8) | −0.0006 (6) | 0.0072 (6) | 0.0011 (6) |
C11 | 0.0375 (8) | 0.0395 (8) | 0.0337 (7) | −0.0003 (6) | 0.0103 (6) | 0.0016 (5) |
C12 | 0.0401 (8) | 0.0514 (9) | 0.0337 (8) | 0.0025 (6) | 0.0024 (6) | −0.0034 (6) |
C13 | 0.0347 (8) | 0.0733 (11) | 0.0461 (9) | −0.0006 (7) | 0.0100 (7) | −0.0076 (8) |
C14 | 0.0410 (8) | 0.0640 (10) | 0.0385 (8) | −0.0023 (7) | 0.0143 (7) | −0.0058 (7) |
C21 | 0.0435 (11) | 0.143 (2) | 0.0542 (12) | 0.0125 (11) | −0.0075 (9) | −0.0168 (11) |
N1 | 0.0432 (7) | 0.0644 (9) | 0.0259 (6) | 0.0056 (6) | 0.0076 (5) | −0.0030 (5) |
N2 | 0.0479 (8) | 0.0582 (9) | 0.0281 (7) | 0.0047 (6) | 0.0068 (5) | −0.0014 (5) |
O1 | 0.0413 (7) | 0.0958 (10) | 0.0534 (8) | 0.0035 (6) | 0.0142 (6) | 0.0052 (6) |
O2 | 0.0480 (7) | 0.0753 (8) | 0.0357 (6) | 0.0072 (5) | 0.0147 (5) | −0.0020 (5) |
O3 | 0.0422 (6) | 0.0685 (7) | 0.0285 (5) | −0.0020 (5) | 0.0093 (4) | 0.0001 (4) |
O4 | 0.0415 (7) | 0.0885 (9) | 0.0347 (6) | 0.0068 (5) | 0.0001 (5) | −0.0039 (5) |
C1—C2 | 1.402 (2) | C9—C10 | 1.404 (2) |
C1—C6 | 1.404 (2) | C10—C11 | 1.3678 (19) |
C1—C7 | 1.476 (2) | C10—H10 | 0.9300 |
C2—O1 | 1.357 (2) | C11—O3 | 1.3712 (16) |
C2—C3 | 1.391 (2) | C11—C12 | 1.400 (2) |
C3—C4 | 1.375 (2) | C12—O4 | 1.3671 (18) |
C3—H3 | 0.9300 | C12—C13 | 1.389 (2) |
C4—C5 | 1.378 (3) | C13—C14 | 1.387 (2) |
C4—H4 | 0.9300 | C13—H13 | 0.9300 |
C5—C6 | 1.375 (2) | C14—H14 | 0.9300 |
C5—H5 | 0.9300 | C21—O4 | 1.409 (2) |
C6—H6 | 0.9300 | C21—H21A | 0.9600 |
C7—O2 | 1.2524 (16) | C21—H21B | 0.9600 |
C7—N1 | 1.337 (2) | C21—H21C | 0.9600 |
C8—N2 | 1.275 (2) | N1—N2 | 1.3840 (17) |
C8—C9 | 1.457 (2) | N1—H1 | 0.8600 |
C8—H8 | 0.9300 | O1—H2 | 1.00 (2) |
C9—C14 | 1.386 (2) | O3—H11 | 0.8200 |
C2—C1—C6 | 117.74 (14) | C11—C10—H10 | 119.7 |
C2—C1—C7 | 119.30 (14) | C9—C10—H10 | 119.7 |
C6—C1—C7 | 122.95 (14) | C10—C11—O3 | 118.55 (12) |
O1—C2—C3 | 118.17 (15) | C10—C11—C12 | 120.27 (13) |
O1—C2—C1 | 121.90 (14) | O3—C11—C12 | 121.17 (13) |
C3—C2—C1 | 119.93 (15) | O4—C12—C13 | 125.99 (14) |
C4—C3—C2 | 120.29 (16) | O4—C12—C11 | 114.52 (13) |
C4—C3—H3 | 119.9 | C13—C12—C11 | 119.49 (14) |
C2—C3—H3 | 119.9 | C14—C13—C12 | 119.95 (15) |
C3—C4—C5 | 121.15 (16) | C14—C13—H13 | 120.0 |
C3—C4—H4 | 119.4 | C12—C13—H13 | 120.0 |
C5—C4—H4 | 119.4 | C9—C14—C13 | 120.79 (14) |
C6—C5—C4 | 118.73 (15) | C9—C14—H14 | 119.6 |
C6—C5—H5 | 120.6 | C13—C14—H14 | 119.6 |
C4—C5—H5 | 120.6 | O4—C21—H21A | 109.5 |
C5—C6—C1 | 122.15 (15) | O4—C21—H21B | 109.5 |
C5—C6—H6 | 118.9 | H21A—C21—H21B | 109.5 |
C1—C6—H6 | 118.9 | O4—C21—H21C | 109.5 |
O2—C7—N1 | 120.78 (13) | H21A—C21—H21C | 109.5 |
O2—C7—C1 | 120.90 (14) | H21B—C21—H21C | 109.5 |
N1—C7—C1 | 118.29 (13) | C7—N1—N2 | 118.93 (12) |
N2—C8—C9 | 120.12 (13) | C7—N1—H1 | 120.5 |
N2—C8—H8 | 119.9 | N2—N1—H1 | 120.5 |
C9—C8—H8 | 119.9 | C8—N2—N1 | 116.24 (13) |
C14—C9—C10 | 118.82 (14) | C2—O1—H2 | 105.6 (12) |
C14—C9—C8 | 120.88 (14) | C11—O3—H11 | 109.5 |
C10—C9—C8 | 120.30 (14) | C12—O4—C21 | 117.93 (14) |
C11—C10—C9 | 120.68 (14) | ||
C6—C1—C2—O1 | 179.36 (13) | C8—C9—C10—C11 | −179.14 (13) |
C7—C1—C2—O1 | 0.7 (2) | C9—C10—C11—O3 | 178.47 (11) |
C6—C1—C2—C3 | −0.1 (2) | C9—C10—C11—C12 | −0.4 (2) |
C7—C1—C2—C3 | −178.83 (13) | C10—C11—C12—O4 | 179.66 (12) |
O1—C2—C3—C4 | −179.71 (15) | O3—C11—C12—O4 | 0.8 (2) |
C1—C2—C3—C4 | −0.2 (2) | C10—C11—C12—C13 | 0.0 (2) |
C2—C3—C4—C5 | 0.3 (3) | O3—C11—C12—C13 | −178.86 (13) |
C3—C4—C5—C6 | −0.1 (2) | O4—C12—C13—C14 | −179.32 (14) |
C4—C5—C6—C1 | −0.2 (2) | C11—C12—C13—C14 | 0.3 (2) |
C2—C1—C6—C5 | 0.4 (2) | C10—C9—C14—C13 | −0.2 (2) |
C7—C1—C6—C5 | 179.01 (13) | C8—C9—C14—C13 | 179.45 (13) |
C2—C1—C7—O2 | 7.4 (2) | C12—C13—C14—C9 | −0.2 (2) |
C6—C1—C7—O2 | −171.25 (13) | O2—C7—N1—N2 | −1.6 (2) |
C2—C1—C7—N1 | −174.64 (12) | C1—C7—N1—N2 | −179.59 (11) |
C6—C1—C7—N1 | 6.7 (2) | C9—C8—N2—N1 | 178.54 (12) |
N2—C8—C9—C14 | 178.18 (13) | C7—N1—N2—C8 | 172.94 (13) |
N2—C8—C9—C10 | −2.2 (2) | C13—C12—O4—C21 | −6.4 (2) |
C14—C9—C10—C11 | 0.5 (2) | C11—C12—O4—C21 | 173.87 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 2.26 | 2.9616 (16) | 138 |
O1—H2···O2 | 1.00 (2) | 1.65 (2) | 2.5424 (19) | 146.3 (19) |
O3—H11···O2ii | 0.82 | 2.17 | 2.8451 (16) | 140 |
O3—H11···O4 | 0.82 | 2.23 | 2.6781 (17) | 115 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+2, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C15H14N2O4 |
Mr | 286.28 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 12.436 (3), 7.1581 (14), 15.048 (3) |
β (°) | 100.95 (3) |
V (Å3) | 1315.2 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.34 × 0.15 × 0.06 |
Data collection | |
Diffractometer | Bruker SMART APEX area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.96, 0.99 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11560, 3288, 2008 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.671 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.166, 1.10 |
No. of reflections | 3288 |
No. of parameters | 196 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.28, −0.26 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 2.26 | 2.9616 (16) | 138.3 |
O1—H2···O2 | 1.00 (2) | 1.65 (2) | 2.5424 (19) | 146.3 (19) |
O3—H11···O2ii | 0.82 | 2.17 | 2.8451 (16) | 139.5 |
O3—H11···O4 | 0.82 | 2.23 | 2.6781 (17) | 114.7 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+2, −y, −z. |
Recently, we have reported a few Schiff base complexes (Qiu, Luo et al., 2006; Qiu, Fang et al., 2006), As an extension of our work on the structural characterization of Schiff base compounds, the crystal structure of the title compound is reported here.
In the title compound, all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). The C8═N2 bond length of 1.275 (2) Å conforms to the value for a double bond. The bond length of 1.337 (2) Å between N1 and C7 is greater than the value for a double bond, and less than the value for a single bond, because of conjugation in the molecule. The dihedral angle between the two rings is 3.7 (2)°.
The crystal structure is stabilized by intermolecular O—H···O and N—H···O hydrogen bonds. (Table 1 and Fig. 2)