A redetermination of 1-{4-[(2-hydroxy­benzyl­idene)­amino]­phenyl}ethano­ne

The crystal structure of the title compound, C₁₅H₁₃NO₂, has been redetermined with better precision and with the location and free refinement of all H atoms [previous report; Rekhlova, Furmanova, Chanturiya & Chikhladze (1991). Kristallografiya, 36, 117–120]. The mol­ecule is present as the phenol–imine tautomeric form with strong intramolec­ular O—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.038
• wR factor = 0.100
• Data-to-parameter ratio = 11.1

checkCIF/PLATON results

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Computing details

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).

1-{4-[(2-Hydroxybenzylidene)amino]phenyl}ethanone

Crystal data

C15H13NO2	F(000) = 504
Mr = 239.26	Dx = 1.312 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10198 reflections
a = 14.7692 (11) Å	θ = 2.9–26°
b = 7.4051 (5) Å	µ = 0.09 mm^−1
c = 11.5752 (14) Å	T = 293 K
β = 106.898 (8)°	Shapeless, orange
V = 1211.29 (19) Å^3	0.50 × 0.29 × 0.16 mm
Z = 4

Data collection

Stoe IPDS-2 diffractometer	2377 independent reflections
Radiation source: fine-focus sealed tube	1639 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.094
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.9°
ω scans	h = −18→18
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −9→8
Tmin = 0.961, Tmax = 0.987	l = −14→14
16727 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: difference Fourier map
wR(F^2) = 0.100	All H-atom parameters refined
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0622P)^2] where P = (Fo^2 + 2Fc^2)/3
2377 reflections	(Δ/σ)max < 0.001
215 parameters	Δρmax = 0.10 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.30978 (9)	0.61072 (17)	0.17464 (11)	0.0465 (3)
C2	0.28788 (10)	0.65244 (19)	0.28184 (12)	0.0520 (3)
C3	0.19454 (11)	0.6570 (2)	0.28224 (16)	0.0651 (4)
C4	0.12343 (11)	0.6212 (2)	0.17817 (16)	0.0684 (4)
C5	0.14357 (11)	0.5789 (2)	0.07273 (15)	0.0642 (4)
C6	0.23609 (10)	0.5735 (2)	0.07152 (13)	0.0545 (4)
C7	0.40627 (9)	0.60464 (18)	0.16988 (12)	0.0483 (3)
C8	0.57003 (9)	0.63749 (18)	0.25507 (11)	0.0460 (3)
C9	0.59484 (9)	0.70132 (19)	0.15573 (12)	0.0508 (3)
C10	0.68816 (9)	0.7054 (2)	0.15792 (12)	0.0520 (4)
C11	0.75919 (9)	0.64788 (18)	0.25814 (12)	0.0488 (3)
C12	0.73379 (10)	0.5850 (2)	0.35685 (13)	0.0542 (4)
C13	0.64050 (10)	0.5794 (2)	0.35562 (12)	0.0530 (4)
C14	0.85911 (10)	0.6588 (2)	0.25629 (14)	0.0600 (4)
C15	0.93619 (13)	0.6154 (4)	0.3697 (2)	0.0822 (6)
N1	0.47618 (7)	0.63696 (16)	0.26260 (9)	0.0503 (3)
O1	0.35657 (9)	0.68860 (16)	0.38500 (9)	0.0704 (3)
O2	0.87831 (7)	0.7011 (2)	0.16486 (11)	0.0849 (4)
H1	0.4145 (9)	0.5728 (18)	0.0915 (13)	0.058 (4)*
H2	0.6233 (9)	0.5354 (19)	0.4211 (13)	0.056 (4)*
H3	0.5476 (10)	0.7464 (19)	0.0858 (13)	0.059 (4)*
H4	0.7046 (9)	0.7487 (18)	0.0917 (13)	0.056 (4)*
H5	0.7805 (10)	0.541 (2)	0.4264 (14)	0.066 (4)*
H6	0.1813 (12)	0.682 (2)	0.3557 (15)	0.072 (5)*
H7	0.2515 (10)	0.545 (2)	−0.0005 (14)	0.065 (4)*
H8	0.0937 (11)	0.547 (2)	−0.0014 (14)	0.071 (4)*
H9	0.0600 (12)	0.632 (2)	0.1774 (15)	0.074 (5)*
H10	0.4143 (16)	0.673 (3)	0.3670 (18)	0.107 (7)*
H11	0.9929 (17)	0.653 (3)	0.3592 (19)	0.112 (7)*
H12	0.9259 (15)	0.681 (3)	0.441 (2)	0.120 (8)*
H13	0.9346 (19)	0.486 (4)	0.387 (2)	0.157 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0495 (7)	0.0422 (7)	0.0493 (7)	0.0003 (5)	0.0169 (6)	0.0028 (5)
C2	0.0569 (8)	0.0519 (8)	0.0510 (7)	−0.0032 (6)	0.0217 (6)	−0.0010 (6)
C3	0.0665 (10)	0.0693 (10)	0.0704 (10)	−0.0017 (8)	0.0370 (8)	−0.0050 (8)
C4	0.0499 (9)	0.0715 (10)	0.0883 (12)	0.0010 (7)	0.0274 (8)	0.0015 (9)
C5	0.0511 (8)	0.0729 (10)	0.0656 (10)	0.0007 (7)	0.0122 (7)	0.0016 (8)
C6	0.0519 (8)	0.0611 (9)	0.0510 (8)	0.0016 (6)	0.0160 (6)	0.0002 (6)
C7	0.0523 (8)	0.0480 (8)	0.0471 (7)	0.0001 (6)	0.0185 (6)	−0.0005 (6)
C8	0.0478 (7)	0.0440 (7)	0.0462 (7)	−0.0015 (5)	0.0139 (6)	−0.0035 (5)
C9	0.0466 (7)	0.0580 (8)	0.0454 (7)	0.0043 (6)	0.0096 (6)	0.0060 (6)
C10	0.0502 (8)	0.0618 (9)	0.0454 (7)	0.0025 (6)	0.0162 (6)	0.0030 (6)
C11	0.0459 (7)	0.0497 (8)	0.0486 (7)	0.0024 (6)	0.0104 (6)	−0.0064 (6)
C12	0.0518 (8)	0.0589 (9)	0.0457 (7)	0.0020 (6)	0.0042 (6)	0.0017 (6)
C13	0.0583 (8)	0.0580 (9)	0.0422 (7)	−0.0050 (6)	0.0136 (6)	0.0019 (6)
C14	0.0495 (8)	0.0678 (10)	0.0613 (9)	0.0021 (7)	0.0140 (7)	−0.0118 (7)
C15	0.0474 (9)	0.1099 (18)	0.0788 (12)	0.0046 (10)	0.0019 (8)	−0.0037 (12)
N1	0.0505 (7)	0.0530 (7)	0.0487 (6)	−0.0022 (5)	0.0162 (5)	−0.0004 (5)
O1	0.0685 (7)	0.0964 (9)	0.0496 (6)	−0.0108 (6)	0.0224 (5)	−0.0145 (5)
O2	0.0560 (6)	0.1315 (11)	0.0720 (8)	0.0011 (6)	0.0260 (6)	−0.0043 (7)

Geometric parameters (Å, º)

C1—C6	1.3893 (19)	C8—N1	1.4138 (17)
C1—C2	1.4046 (18)	C9—C10	1.3714 (19)
C1—C7	1.4428 (18)	C9—H3	0.962 (14)
C2—O1	1.3500 (17)	C10—C11	1.3857 (18)
C2—C3	1.380 (2)	C10—H4	0.926 (15)
C3—C4	1.374 (2)	C11—C12	1.383 (2)
C3—H6	0.945 (17)	C11—C14	1.484 (2)
C4—C5	1.374 (2)	C12—C13	1.374 (2)
C4—H9	0.938 (17)	C12—H5	0.952 (15)
C5—C6	1.371 (2)	C13—H2	0.926 (15)
C5—H8	0.983 (15)	C14—O2	1.2138 (19)
C6—H7	0.949 (15)	C14—C15	1.501 (2)
C7—N1	1.2772 (16)	C15—H11	0.92 (2)
C7—H1	0.978 (15)	C15—H12	1.00 (2)
C8—C13	1.3853 (18)	C15—H13	0.98 (3)
C8—C9	1.3874 (18)	O1—H10	0.94 (2)
C6—C1—C2	118.60 (12)	C10—C9—H3	119.1 (8)
C6—C1—C7	119.78 (12)	C8—C9—H3	121.0 (8)
C2—C1—C7	121.62 (12)	C9—C10—C11	121.40 (14)
O1—C2—C3	119.12 (13)	C9—C10—H4	119.8 (8)
O1—C2—C1	121.22 (12)	C11—C10—H4	118.8 (8)
C3—C2—C1	119.67 (13)	C12—C11—C10	118.29 (12)
C4—C3—C2	120.12 (15)	C12—C11—C14	122.68 (12)
C4—C3—H6	121.4 (10)	C10—C11—C14	119.02 (13)
C2—C3—H6	118.5 (10)	C13—C12—C11	120.90 (13)
C5—C4—C3	120.99 (15)	C13—C12—H5	118.4 (9)
C5—C4—H9	119.0 (10)	C11—C12—H5	120.7 (9)
C3—C4—H9	119.9 (10)	C12—C13—C8	120.36 (14)
C6—C5—C4	119.31 (15)	C12—C13—H2	121.0 (8)
C6—C5—H8	118.7 (9)	C8—C13—H2	118.6 (8)
C4—C5—H8	122.0 (9)	O2—C14—C11	120.79 (13)
C5—C6—C1	121.30 (14)	O2—C14—C15	120.52 (15)
C5—C6—H7	120.6 (9)	C11—C14—C15	118.69 (16)
C1—C6—H7	118.1 (9)	C14—C15—H11	107.8 (13)
N1—C7—C1	121.89 (12)	C14—C15—H12	110.9 (13)
N1—C7—H1	122.5 (8)	H11—C15—H12	108.8 (18)
C1—C7—H1	115.6 (8)	C14—C15—H13	109.5 (16)
C13—C8—C9	119.16 (12)	H11—C15—H13	113 (2)
C13—C8—N1	117.26 (12)	H12—C15—H13	106 (2)
C9—C8—N1	123.50 (11)	C7—N1—C8	121.09 (11)
C10—C9—C8	119.89 (12)	C2—O1—H10	106.0 (12)
C6—C1—C2—O1	179.56 (13)	C8—C9—C10—C11	−0.4 (2)
C7—C1—C2—O1	0.0 (2)	C9—C10—C11—C12	0.2 (2)
C6—C1—C2—C3	−0.5 (2)	C9—C10—C11—C14	−178.80 (13)
C7—C1—C2—C3	179.90 (14)	C10—C11—C12—C13	0.1 (2)
O1—C2—C3—C4	179.80 (14)	C14—C11—C12—C13	179.08 (14)
C1—C2—C3—C4	−0.1 (2)	C11—C12—C13—C8	−0.2 (2)
C2—C3—C4—C5	0.6 (3)	C9—C8—C13—C12	0.0 (2)
C3—C4—C5—C6	−0.4 (3)	N1—C8—C13—C12	−176.69 (13)
C4—C5—C6—C1	−0.3 (2)	C12—C11—C14—O2	174.13 (15)
C2—C1—C6—C5	0.7 (2)	C10—C11—C14—O2	−6.9 (2)
C7—C1—C6—C5	−179.68 (14)	C12—C11—C14—C15	−5.6 (2)
C6—C1—C7—N1	−179.62 (12)	C10—C11—C14—C15	173.43 (16)
C2—C1—C7—N1	−0.1 (2)	C1—C7—N1—C8	−177.43 (12)
C13—C8—C9—C10	0.3 (2)	C13—C8—N1—C7	−146.92 (13)
N1—C8—C9—C10	176.78 (13)	C9—C8—N1—C7	36.54 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H10···N1	0.94 (2)	1.73 (2)	2.5941 (15)	150.2 (18)