The molecule of the title compound, C
15H
13NO
3, is not planar and the dihedral angle between the planes of the two aromatic rings is 53.93 (7)°. The molecule exists in the crystal structure in the phenol–imine tautomeric form and has two `active' H atoms, which participate in strong intramolecular O—H
N and O—H
O hydrogen bonds. One of the H atoms is also involved in an intermolecular hydrogen bond, which links the molecules into centrosymmetric dimers.
Supporting information
CCDC reference: 239259
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.035
- wR factor = 0.086
- Data-to-parameter ratio = 10.8
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSMU01_ALERT_1_C The ratio of given/expected absorption coefficient lies
outside the range 0.99 <> 1.01
Calculated value of mu = 0.097
Value of mu given = 0.100
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
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (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).
3-(4-acetylphenyliminomethyl)-1,2-dihydroxybenzene
top
Crystal data top
C15H13NO3 | F(000) = 536 |
Mr = 255.26 | Dx = 1.376 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7244 reflections |
a = 10.0014 (11) Å | θ = 2.1–26.0° |
b = 14.4188 (4) Å | µ = 0.10 mm−1 |
c = 8.8212 (10) Å | T = 293 K |
β = 104.413 (9)° | Irregular shape, red |
V = 1232.1 (2) Å3 | 0.46 × 0.32 × 0.19 mm |
Z = 4 | |
Data collection top
STOE IPDS-II diffractometer | 2425 independent reflections |
Radiation source: fine-focus sealed tube | 1660 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.037 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.1° |
ω scans | h = −12→12 |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | k = −17→17 |
Tmin = 0.970, Tmax = 0.985 | l = −10→10 |
8659 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)] = 0.035 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.086 | All H-atom parameters refined |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0514P)2] where P = (Fo2 + 2Fc2)/3 |
2425 reflections | (Δ/σ)max < 0.001 |
224 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.16 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 | |
O2 | 0.55586 (13) | 0.46978 (9) | 0.84987 (12) | 0.0580 (3) | |
O1 | 0.70992 (11) | 0.50751 (8) | 0.64901 (12) | 0.0523 (3) | |
C3 | 0.52248 (15) | 0.54326 (10) | 0.75121 (15) | 0.0440 (3) | |
C10 | 0.84259 (16) | 0.62782 (11) | 0.04454 (16) | 0.0492 (4) | |
C9 | 0.76274 (18) | 0.62350 (12) | 0.15136 (17) | 0.0521 (4) | |
C14 | 1.07508 (16) | 0.63265 (9) | −0.01811 (16) | 0.0428 (3) | |
C2 | 0.60087 (14) | 0.56326 (10) | 0.64451 (14) | 0.0410 (3) | |
C4 | 0.41090 (17) | 0.59726 (11) | 0.75590 (17) | 0.0503 (4) | |
C11 | 0.98517 (14) | 0.63285 (9) | 0.09271 (14) | 0.0397 (3) | |
C8 | 0.82638 (15) | 0.62238 (10) | 0.31062 (15) | 0.0451 (4) | |
N1 | 0.75152 (14) | 0.60949 (9) | 0.42569 (13) | 0.0494 (3) | |
C1 | 0.56377 (15) | 0.63732 (10) | 0.54016 (15) | 0.0442 (3) | |
C5 | 0.37438 (19) | 0.67110 (12) | 0.65300 (18) | 0.0550 (4) | |
C12 | 1.04739 (16) | 0.63392 (10) | 0.25338 (16) | 0.0445 (3) | |
C7 | 0.64343 (17) | 0.65594 (11) | 0.42548 (16) | 0.0478 (4) | |
C6 | 0.44973 (17) | 0.69080 (12) | 0.54618 (18) | 0.0524 (4) | |
C13 | 0.96902 (16) | 0.62716 (11) | 0.36009 (16) | 0.0481 (4) | |
O3 | 1.19995 (12) | 0.63666 (9) | 0.03049 (12) | 0.0624 (3) | |
C15 | 1.0121 (2) | 0.62535 (15) | −0.18986 (18) | 0.0577 (4) | |
H7 | 0.6109 (17) | 0.7077 (11) | 0.3502 (19) | 0.062 (5)* | |
H5 | 0.2972 (17) | 0.7092 (11) | 0.6574 (17) | 0.051 (4)* | |
H6 | 0.4310 (15) | 0.7404 (11) | 0.4773 (17) | 0.050 (4)* | |
H4 | 0.3578 (16) | 0.5833 (10) | 0.8295 (17) | 0.051 (4)* | |
H12 | 1.1459 (18) | 0.6360 (10) | 0.2867 (17) | 0.050 (4)* | |
H9 | 0.6654 (18) | 0.6171 (10) | 0.1180 (18) | 0.058 (5)* | |
H13 | 1.0143 (17) | 0.6253 (11) | 0.470 (2) | 0.059 (4)* | |
H10 | 0.7986 (17) | 0.6280 (11) | −0.067 (2) | 0.062 (5)* | |
H1 | 0.752 (2) | 0.5318 (14) | 0.566 (2) | 0.093 (6)* | |
H2 | 0.633 (2) | 0.4450 (15) | 0.832 (2) | 0.092 (7)* | |
H15C | 1.077 (2) | 0.6306 (13) | −0.246 (2) | 0.085 (6)* | |
H15A | 0.966 (2) | 0.5681 (17) | −0.215 (2) | 0.101 (8)* | |
H15B | 0.938 (2) | 0.6703 (16) | −0.232 (3) | 0.097 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.0514 (7) | 0.0757 (8) | 0.0520 (6) | 0.0074 (6) | 0.0224 (5) | 0.0175 (5) |
O1 | 0.0441 (6) | 0.0664 (7) | 0.0503 (6) | 0.0085 (5) | 0.0190 (5) | 0.0111 (5) |
C3 | 0.0415 (8) | 0.0544 (9) | 0.0363 (6) | −0.0036 (7) | 0.0103 (6) | 0.0015 (6) |
C10 | 0.0461 (9) | 0.0652 (10) | 0.0356 (7) | −0.0054 (8) | 0.0086 (6) | 0.0018 (6) |
C9 | 0.0395 (9) | 0.0726 (11) | 0.0450 (8) | −0.0042 (8) | 0.0120 (6) | 0.0040 (7) |
C14 | 0.0474 (10) | 0.0398 (7) | 0.0442 (7) | −0.0035 (7) | 0.0166 (6) | −0.0006 (6) |
C2 | 0.0348 (8) | 0.0515 (8) | 0.0370 (7) | −0.0020 (6) | 0.0094 (5) | −0.0050 (6) |
C4 | 0.0470 (9) | 0.0642 (10) | 0.0448 (8) | −0.0013 (8) | 0.0210 (7) | −0.0036 (7) |
C11 | 0.0442 (8) | 0.0368 (7) | 0.0393 (7) | −0.0015 (6) | 0.0129 (6) | 0.0016 (5) |
C8 | 0.0492 (9) | 0.0489 (8) | 0.0401 (7) | −0.0020 (7) | 0.0168 (6) | 0.0034 (6) |
N1 | 0.0492 (8) | 0.0608 (8) | 0.0418 (6) | −0.0029 (6) | 0.0184 (5) | 0.0016 (5) |
C1 | 0.0461 (9) | 0.0497 (8) | 0.0378 (7) | −0.0040 (7) | 0.0123 (6) | −0.0022 (6) |
C5 | 0.0544 (10) | 0.0612 (10) | 0.0536 (9) | 0.0099 (8) | 0.0215 (7) | −0.0016 (7) |
C12 | 0.0397 (9) | 0.0524 (9) | 0.0411 (7) | −0.0001 (7) | 0.0096 (6) | −0.0014 (6) |
C7 | 0.0515 (10) | 0.0522 (9) | 0.0410 (7) | −0.0037 (8) | 0.0138 (6) | 0.0014 (7) |
C6 | 0.0563 (10) | 0.0538 (9) | 0.0493 (8) | 0.0070 (8) | 0.0172 (7) | 0.0031 (7) |
C13 | 0.0494 (9) | 0.0602 (9) | 0.0351 (7) | 0.0016 (8) | 0.0110 (6) | 0.0025 (6) |
O3 | 0.0467 (7) | 0.0885 (9) | 0.0558 (6) | −0.0028 (6) | 0.0202 (5) | 0.0013 (6) |
C15 | 0.0667 (12) | 0.0712 (12) | 0.0400 (8) | −0.0105 (11) | 0.0219 (8) | −0.0052 (8) |
Geometric parameters (Å, º) top
O1—C2 | 1.3475 (17) | C14—C15 | 1.493 (2) |
O2—C3 | 1.3590 (18) | C4—C5 | 1.388 (2) |
O3—C14 | 1.2166 (17) | C4—H4 | 0.957 (16) |
N1—C7 | 1.271 (2) | C11—C12 | 1.3989 (19) |
N1—C8 | 1.4155 (18) | C8—C13 | 1.386 (2) |
C1—C2 | 1.3983 (19) | C1—C6 | 1.389 (2) |
C1—C7 | 1.460 (2) | C5—C6 | 1.375 (2) |
C11—C14 | 1.4839 (19) | C5—H5 | 0.956 (16) |
O2—H2 | 0.90 (2) | C12—C13 | 1.370 (2) |
O1—H1 | 1.00 (2) | C12—H12 | 0.956 (17) |
C3—C4 | 1.370 (2) | C7—H7 | 0.998 (16) |
C3—C2 | 1.3968 (19) | C6—H6 | 0.927 (15) |
C10—C9 | 1.380 (2) | C13—H13 | 0.961 (16) |
C10—C11 | 1.385 (2) | C15—H15C | 0.91 (2) |
C10—H10 | 0.974 (16) | C15—H15A | 0.95 (2) |
C9—C8 | 1.391 (2) | C15—H15B | 0.98 (2) |
C9—H9 | 0.949 (17) | | |
| | | |
C7—N1—C8 | 122.08 (13) | C10—C11—C14 | 122.98 (12) |
C2—C1—C7 | 119.70 (13) | C12—C11—C14 | 118.54 (13) |
O1—C2—C3 | 116.29 (12) | C13—C8—C9 | 119.60 (13) |
O1—C2—C1 | 123.72 (12) | C6—C1—C2 | 119.00 (13) |
C3—O2—H2 | 106.4 (13) | C6—C1—C7 | 121.29 (14) |
C2—O1—H1 | 104.8 (12) | C6—C5—C4 | 120.45 (16) |
O2—C3—C4 | 119.73 (13) | C6—C5—H5 | 119.7 (9) |
O2—C3—C2 | 120.19 (13) | C4—C5—H5 | 119.8 (9) |
N1—C7—C1 | 120.84 (14) | C13—C12—C11 | 120.60 (14) |
C13—C8—N1 | 117.87 (12) | C13—C12—H12 | 120.9 (9) |
C9—C8—N1 | 122.36 (14) | C11—C12—H12 | 118.5 (9) |
C4—C3—C2 | 120.07 (13) | N1—C7—H7 | 122.1 (9) |
C9—C10—C11 | 121.31 (13) | C1—C7—H7 | 117.1 (9) |
C9—C10—H10 | 119.9 (10) | C5—C6—C1 | 120.47 (15) |
C11—C10—H10 | 118.8 (10) | C5—C6—H6 | 123.6 (10) |
C10—C9—C8 | 119.55 (15) | C1—C6—H6 | 115.9 (10) |
C10—C9—H9 | 121.1 (10) | C12—C13—C8 | 120.48 (13) |
C8—C9—H9 | 119.2 (10) | C12—C13—H13 | 119.1 (10) |
O3—C14—C11 | 120.33 (12) | C8—C13—H13 | 120.4 (10) |
O3—C14—C15 | 119.87 (14) | C14—C15—H15C | 111.6 (13) |
C11—C14—C15 | 119.79 (14) | C14—C15—H15A | 111.2 (13) |
C3—C2—C1 | 119.98 (13) | H15C—C15—H15A | 108.3 (17) |
C3—C4—C5 | 120.01 (14) | C14—C15—H15B | 115.3 (13) |
C3—C4—H4 | 119.6 (9) | H15C—C15—H15B | 107.9 (17) |
C5—C4—H4 | 120.4 (9) | H15A—C15—H15B | 101.9 (19) |
C10—C11—C12 | 118.41 (12) | | |
| | | |
C11—C10—C9—C8 | −1.2 (2) | O1—C2—C1—C6 | −179.62 (14) |
O2—C3—C2—O1 | −1.39 (19) | C3—C2—C1—C6 | 0.9 (2) |
C4—C3—C2—O1 | 179.13 (13) | O1—C2—C1—C7 | 1.5 (2) |
O2—C3—C2—C1 | 178.16 (12) | C3—C2—C1—C7 | −177.97 (13) |
C4—C3—C2—C1 | −1.3 (2) | C3—C4—C5—C6 | −0.2 (2) |
O2—C3—C4—C5 | −178.51 (14) | C10—C11—C12—C13 | 2.0 (2) |
C2—C3—C4—C5 | 1.0 (2) | C14—C11—C12—C13 | −175.11 (14) |
C9—C10—C11—C12 | −0.3 (2) | C8—N1—C7—C1 | 176.34 (13) |
C9—C10—C11—C14 | 176.71 (14) | C6—C1—C7—N1 | 176.60 (14) |
O3—C14—C11—C10 | −179.56 (15) | C2—C1—C7—N1 | −4.6 (2) |
C15—C14—C11—C10 | −0.9 (2) | C4—C5—C6—C1 | −0.3 (2) |
O3—C14—C11—C12 | −2.6 (2) | C2—C1—C6—C5 | −0.1 (2) |
C15—C14—C11—C12 | 176.06 (15) | C7—C1—C6—C5 | 178.73 (14) |
C10—C9—C8—C13 | 1.1 (2) | C11—C12—C13—C8 | −2.2 (2) |
C10—C9—C8—N1 | −174.08 (15) | C9—C8—C13—C12 | 0.7 (2) |
C13—C8—N1—C7 | 135.50 (16) | N1—C8—C13—C12 | 176.03 (14) |
C9—C8—N1—C7 | −49.3 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3i | 0.90 (2) | 2.15 (2) | 2.8550 (17) | 134.3 (18) |
O2—H2···O1 | 0.90 (2) | 2.15 (2) | 2.6774 (15) | 116.5 (17) |
O1—H1···N1 | 1.00 (2) | 1.67 (2) | 2.5737 (15) | 149.2 (19) |
Symmetry code: (i) −x+2, −y+1, −z+1. |