The title compound, C
15H
14N
2O
2, is stabilized in the solid state as an enol–imine tautomer, with one strong intramolecular O—H

N hydrogen bond and four C—H

O and one C—H

N intermolecular interaction that generate edge-fused [
S(6)
R22(8)
R22(8)
R54(32)] motifs. The molecule is approximately planar, with a dihedral angle of 1.72 (3)° between the two aromatic rings.
Supporting information
CCDC reference: 643114
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.032
- wR factor = 0.080
- Data-to-parameter ratio = 7.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.67 mm
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.49
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8B .. O2 .. 2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. O2 .. 2.76 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14 .. O1 .. 2.77 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15B .. O2 .. 2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7 .. N2 .. 2.67 Ang.
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 26.00
From the CIF: _reflns_number_total 1303
Count of symmetry unique reflns 1304
Completeness (_total/calc) 99.92%
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
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
1 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
2 ALERT type 3 Indicator that the structure quality may be low
6 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
(
E)-2-Hydroxy-5-methyl-3-[(4-methyl-2-pyridyl)iminomethyl]benzaldehyde
top
Crystal data top
C15H14N2O2 | F(000) = 268 |
Mr = 254.28 | Dx = 1.283 Mg m−3 |
Monoclinic, Pc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -2yc | Cell parameters from 10340 reflections |
a = 7.4936 (7) Å | θ = 2.1–27.8° |
b = 4.5019 (3) Å | µ = 0.09 mm−1 |
c = 20.677 (2) Å | T = 296 K |
β = 109.273 (7)° | Prism, red |
V = 658.46 (10) Å3 | 0.67 × 0.42 × 0.21 mm |
Z = 2 | |
Data collection top
Stoe IPDS-II diffractometer | 1303 independent reflections |
Radiation source: fine-focus sealed tube | 1021 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.060 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.1° |
ω scans | h = −9→9 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −5→5 |
Tmin = 0.954, Tmax = 0.984 | l = −25→25 |
10340 measured reflections | |
Refinement top
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0536P)2] where P = (Fo2 + 2Fc2)/3 |
1303 reflections | (Δ/σ)max < 0.001 |
174 parameters | Δρmax = 0.09 e Å−3 |
2 restraints | Δρmin = −0.09 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.4317 (3) | −0.0013 (5) | 0.57367 (11) | 0.0488 (6) | |
C2 | 0.2426 (3) | −0.0952 (5) | 0.56069 (12) | 0.0501 (6) | |
C3 | 0.2016 (3) | −0.3027 (6) | 0.60417 (12) | 0.0538 (6) | |
C4 | 0.3481 (3) | −0.4155 (6) | 0.65903 (13) | 0.0545 (6) | |
H4 | 0.3197 | −0.5541 | 0.6875 | 0.065* | |
C5 | 0.5350 (3) | −0.3302 (5) | 0.67320 (13) | 0.0531 (6) | |
C6 | 0.5718 (3) | −0.1245 (6) | 0.62960 (13) | 0.0539 (6) | |
H6 | 0.6963 | −0.0652 | 0.6380 | 0.065* | |
C7 | 0.0078 (4) | −0.4072 (7) | 0.59118 (15) | 0.0687 (7) | |
H7 | −0.0858 | −0.3355 | 0.5525 | 0.082* | |
C8 | 0.6893 (4) | −0.4615 (7) | 0.73225 (14) | 0.0678 (7) | |
H8A | 0.7556 | −0.3054 | 0.7622 | 0.081* | |
H8B | 0.7758 | −0.5682 | 0.7154 | 0.081* | |
H8C | 0.6354 | −0.5949 | 0.7570 | 0.081* | |
C9 | 0.4811 (3) | 0.2133 (6) | 0.53053 (14) | 0.0538 (6) | |
H9 | 0.6070 | 0.2674 | 0.5402 | 0.065* | |
C10 | 0.4038 (3) | 0.5390 (6) | 0.43680 (12) | 0.0529 (6) | |
C11 | 0.2599 (4) | 0.6570 (5) | 0.38320 (13) | 0.0579 (7) | |
H11 | 0.1355 | 0.6016 | 0.3765 | 0.069* | |
C12 | 0.2991 (4) | 0.8583 (6) | 0.33903 (14) | 0.0613 (7) | |
C13 | 0.4866 (4) | 0.9297 (7) | 0.35246 (16) | 0.0696 (7) | |
H13 | 0.5221 | 1.0589 | 0.3238 | 0.084* | |
C14 | 0.6213 (4) | 0.8077 (7) | 0.40885 (15) | 0.0706 (8) | |
H14 | 0.7460 | 0.8680 | 0.4182 | 0.085* | |
C15 | 0.1434 (5) | 0.9910 (8) | 0.27985 (16) | 0.0814 (9) | |
H15A | 0.0267 | 0.9844 | 0.2895 | 0.098* | |
H15B | 0.1306 | 0.8797 | 0.2390 | 0.098* | |
H15C | 0.1739 | 1.1936 | 0.2734 | 0.098* | |
N1 | 0.3543 (3) | 0.3305 (5) | 0.47917 (11) | 0.0544 (5) | |
N2 | 0.5855 (3) | 0.6104 (5) | 0.45063 (13) | 0.0645 (6) | |
O1 | 0.1024 (2) | 0.0140 (4) | 0.50696 (9) | 0.0645 (5) | |
H1 | 0.1462 | 0.1326 | 0.4861 | 0.097* | |
O2 | −0.0382 (3) | −0.5808 (5) | 0.62748 (11) | 0.0854 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0501 (13) | 0.0433 (12) | 0.0549 (14) | −0.0034 (11) | 0.0197 (11) | −0.0066 (11) |
C2 | 0.0465 (13) | 0.0516 (14) | 0.0528 (13) | −0.0009 (11) | 0.0174 (11) | −0.0063 (12) |
C3 | 0.0511 (14) | 0.0541 (15) | 0.0605 (16) | −0.0024 (11) | 0.0245 (13) | −0.0040 (12) |
C4 | 0.0532 (13) | 0.0560 (14) | 0.0598 (14) | 0.0028 (12) | 0.0261 (11) | −0.0027 (13) |
C5 | 0.0509 (13) | 0.0511 (13) | 0.0580 (14) | 0.0018 (11) | 0.0190 (11) | −0.0076 (11) |
C6 | 0.0474 (13) | 0.0524 (14) | 0.0627 (15) | −0.0043 (10) | 0.0194 (12) | −0.0113 (12) |
C7 | 0.0503 (14) | 0.089 (2) | 0.0697 (15) | −0.0005 (13) | 0.0238 (12) | 0.0141 (15) |
C8 | 0.0585 (14) | 0.0744 (18) | 0.0698 (17) | 0.0047 (14) | 0.0200 (12) | 0.0022 (16) |
C9 | 0.0518 (13) | 0.0483 (13) | 0.0647 (14) | −0.0083 (11) | 0.0241 (12) | −0.0091 (12) |
C10 | 0.0595 (15) | 0.0450 (13) | 0.0591 (15) | −0.0075 (11) | 0.0261 (12) | −0.0085 (11) |
C11 | 0.0611 (15) | 0.0512 (14) | 0.0600 (15) | −0.0088 (12) | 0.0180 (13) | −0.0084 (12) |
C12 | 0.0797 (19) | 0.0510 (14) | 0.0534 (14) | −0.0036 (12) | 0.0221 (13) | −0.0064 (11) |
C13 | 0.087 (2) | 0.0634 (17) | 0.0661 (17) | −0.0102 (15) | 0.0352 (16) | 0.0044 (15) |
C14 | 0.0639 (17) | 0.078 (2) | 0.078 (2) | −0.0122 (15) | 0.0343 (16) | 0.0037 (17) |
C15 | 0.093 (2) | 0.0723 (19) | 0.0681 (18) | −0.0044 (17) | 0.0116 (16) | 0.0044 (17) |
N1 | 0.0585 (12) | 0.0471 (11) | 0.0591 (12) | −0.0057 (9) | 0.0216 (11) | −0.0045 (10) |
N2 | 0.0593 (13) | 0.0653 (14) | 0.0715 (14) | −0.0083 (11) | 0.0250 (11) | 0.0010 (12) |
O1 | 0.0506 (10) | 0.0742 (11) | 0.0667 (10) | −0.0026 (8) | 0.0165 (8) | 0.0102 (9) |
O2 | 0.0613 (11) | 0.1133 (16) | 0.0887 (13) | −0.0101 (11) | 0.0342 (10) | 0.0251 (13) |
Geometric parameters (Å, º) top
C1—C6 | 1.395 (3) | C9—N1 | 1.282 (3) |
C1—C2 | 1.417 (3) | C9—H9 | 0.9300 |
C1—C9 | 1.443 (4) | C10—N2 | 1.335 (3) |
C2—O1 | 1.345 (3) | C10—C11 | 1.373 (4) |
C2—C3 | 1.399 (3) | C10—N1 | 1.414 (3) |
C3—C4 | 1.388 (3) | C11—C12 | 1.385 (4) |
C3—C7 | 1.464 (3) | C11—H11 | 0.9300 |
C4—C5 | 1.387 (4) | C12—C13 | 1.377 (4) |
C4—H4 | 0.9300 | C12—C15 | 1.508 (4) |
C5—C6 | 1.383 (3) | C13—C14 | 1.379 (4) |
C5—C8 | 1.498 (4) | C13—H13 | 0.9300 |
C6—H6 | 0.9300 | C14—N2 | 1.327 (4) |
C7—O2 | 1.210 (3) | C14—H14 | 0.9300 |
C7—H7 | 0.9300 | C15—H15A | 0.9600 |
C8—H8A | 0.9600 | C15—H15B | 0.9600 |
C8—H8B | 0.9600 | C15—H15C | 0.9600 |
C8—H8C | 0.9600 | O1—H1 | 0.8200 |
| | | |
C6—C1—C2 | 118.1 (2) | N1—C9—C1 | 121.1 (2) |
C6—C1—C9 | 120.1 (2) | N1—C9—H9 | 119.5 |
C2—C1—C9 | 121.8 (2) | C1—C9—H9 | 119.5 |
O1—C2—C3 | 119.82 (19) | N2—C10—C11 | 123.6 (2) |
O1—C2—C1 | 120.5 (2) | N2—C10—N1 | 119.0 (2) |
C3—C2—C1 | 119.7 (2) | C11—C10—N1 | 117.4 (2) |
C4—C3—C2 | 119.1 (2) | C10—C11—C12 | 120.3 (2) |
C4—C3—C7 | 120.1 (2) | C10—C11—H11 | 119.9 |
C2—C3—C7 | 120.8 (2) | C12—C11—H11 | 119.9 |
C5—C4—C3 | 122.8 (3) | C13—C12—C11 | 116.4 (3) |
C5—C4—H4 | 118.6 | C13—C12—C15 | 122.4 (3) |
C3—C4—H4 | 118.6 | C11—C12—C15 | 121.2 (3) |
C6—C5—C4 | 116.9 (2) | C12—C13—C14 | 119.4 (3) |
C6—C5—C8 | 121.9 (2) | C12—C13—H13 | 120.3 |
C4—C5—C8 | 121.1 (3) | C14—C13—H13 | 120.3 |
C5—C6—C1 | 123.3 (2) | N2—C14—C13 | 124.6 (3) |
C5—C6—H6 | 118.3 | N2—C14—H14 | 117.7 |
C1—C6—H6 | 118.3 | C13—C14—H14 | 117.7 |
O2—C7—C3 | 124.2 (2) | C12—C15—H15A | 109.5 |
O2—C7—H7 | 117.9 | C12—C15—H15B | 109.5 |
C3—C7—H7 | 117.9 | H15A—C15—H15B | 109.5 |
C5—C8—H8A | 109.5 | C12—C15—H15C | 109.5 |
C5—C8—H8B | 109.5 | H15A—C15—H15C | 109.5 |
H8A—C8—H8B | 109.5 | H15B—C15—H15C | 109.5 |
C5—C8—H8C | 109.5 | C9—N1—C10 | 120.80 (19) |
H8A—C8—H8C | 109.5 | C14—N2—C10 | 115.7 (3) |
H8B—C8—H8C | 109.5 | C2—O1—H1 | 109.5 |
| | | |
C6—C1—C2—O1 | −179.2 (2) | C2—C3—C7—O2 | −178.2 (3) |
C9—C1—C2—O1 | 0.2 (3) | C6—C1—C9—N1 | −179.5 (2) |
C6—C1—C2—C3 | 0.9 (3) | C2—C1—C9—N1 | 1.0 (3) |
C9—C1—C2—C3 | −179.7 (2) | N2—C10—C11—C12 | 1.2 (4) |
O1—C2—C3—C4 | 179.4 (2) | N1—C10—C11—C12 | −178.8 (2) |
C1—C2—C3—C4 | −0.7 (3) | C10—C11—C12—C13 | −0.2 (4) |
O1—C2—C3—C7 | 1.1 (4) | C10—C11—C12—C15 | −179.9 (3) |
C1—C2—C3—C7 | −178.9 (2) | C11—C12—C13—C14 | −2.0 (4) |
C2—C3—C4—C5 | 0.4 (4) | C15—C12—C13—C14 | 177.8 (3) |
C7—C3—C4—C5 | 178.6 (2) | C12—C13—C14—N2 | 3.5 (5) |
C3—C4—C5—C6 | −0.2 (4) | C1—C9—N1—C10 | −179.5 (2) |
C3—C4—C5—C8 | −178.9 (2) | N2—C10—N1—C9 | 0.7 (3) |
C4—C5—C6—C1 | 0.4 (3) | C11—C10—N1—C9 | −179.4 (2) |
C8—C5—C6—C1 | 179.1 (2) | C13—C14—N2—C10 | −2.5 (4) |
C2—C1—C6—C5 | −0.7 (4) | C11—C10—N2—C14 | 0.2 (4) |
C9—C1—C6—C5 | 179.8 (2) | N1—C10—N2—C14 | −179.9 (2) |
C4—C3—C7—O2 | 3.6 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.84 | 2.576 (3) | 148 |
C8—H8B···O2i | 0.96 | 2.63 | 3.474 (4) | 147 |
C9—H9···O2ii | 0.93 | 2.76 | 3.618 (3) | 153 |
C14—H14···O1ii | 0.93 | 2.77 | 3.626 (3) | 153 |
C15—H15B···O2iii | 0.96 | 2.61 | 3.516 (4) | 158 |
C7—H7···N2iv | 0.93 | 2.67 | 3.521 (4) | 152 |
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z; (iii) x, −y, z−1/2; (iv) x−1, y−1, z. |