3-(2-Hydroxy­benzyl­ideneamino)benzonitrile

In the title mol­ecule, C₁₄H₁₀N₂O, an intra­molecular O—H...N hydrogen bond contributes to the essential coplanarity of the two benzene rings, which form a dihedral angle of 6.04 (18)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.056
• wR factor = 0.122
• Data-to-parameter ratio = 8.4

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.812     1.000
            Tmin(prime) and Tmax expected:      0.981     0.996
            RR(prime) =      0.824
            Please check that your absorption correction is appropriate.
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.116
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.82
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C10    -   C14    ...       1.44 Ang.

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.996
            Tmax scaled      0.996 Tmin scaled      0.809
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           27.48
           From the CIF: _reflns_number_total               1339
           Count of symmetry unique reflns         1340
           Completeness (_total/calc)             99.93%
           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
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
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
   6 ALERT level C = Check and explain
   5 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   7 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

---

S1. Comment

Schiff base compounds have attracted great attention for many years. These compounds play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism, photochromism and thermochromism. Here, we report the crystal structure of the title compound.

In the title compound (Fig. 1), all bond lengths are within normal ranges. The C7=N1 bond length of 1.277 (4)Å is a typical double bond, similar to the corresponding bond lengths in 4-methoxy-2-[(4-nitrophenyl)iminomethyl]phenol (Kosar et al., 2005). The molecule is almost planar and displays a trans configuration with respect to the C7=N1 double bond. The dihedral angle between the benzene rings is 6.04 (18)°. Strong intramolecular O—H···N hydrogen-bond interaction (Talbe I), similar to the reported earlier (Cheng et al., 2005, 2006), is observed in the molecule.

Related literature

For related crystal structures, see: Kosar et al. (2005); Cheng et al. (2005, 2006).

S2. Experimental

3-Aminobenzonitrile and salicylaldehyde were available commercially and were used without further purification. 3-Aminobenzonitrile (1.18 g, 10 mmol) and salicylaldehyde (1.22 g, 10 mmol) were dissolved in ethanol (20 ml). The mixture was heated to reflux for 4 h, then cooled to room temperature overnight and large amounts of a yellow precipitate were formed. Yellow crystals were obtained by recrystallization from ethyl alcohol (yield: 82%). For the X-ray diffraction analysis, suitable single crystals were obtained after one week by slow evaporation from an ethyl alcohol solution.

S3. Refinement

C-bound H atoms were geometrically positioned (C—H 0.93 Å) and refined as riding with U_iso(H)= 1.2Ueq(C). Atom H1B was located on a difference map and refined isotropically with bon restraint O1—H1B = 0.82 (2) Å. In the absence of significant anomalous scatterers, 1124 Friedel pairs were merged.

Computing details

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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).

Figures

Fig. 1. The molecular structure of the title compound with atomic numbering and displacement ellipsoids drawn at the 30% probability level.

3-(2-Hydroxybenzylideneamino)benzonitrile

Crystal data

C14H10N2O	F(000) = 464
Mr = 222.24	Dx = 1.324 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 8294 reflections
a = 26.397 (5) Å	θ = 3.0–27.6°
b = 3.9211 (8) Å	µ = 0.09 mm^−1
c = 10.773 (2) Å	T = 293 K
V = 1115.1 (4) Å^3	Stick, yellow
Z = 4	0.22 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 diffractometer	1339 independent reflections
Radiation source: fine-focus sealed tube	901 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.116
Detector resolution: 13.6612 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −34→34
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −5→5
Tmin = 0.812, Tmax = 1.00	l = −13→13
9995 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0413P)^2] where P = (Fo^2 + 2Fc^2)/3
1339 reflections	(Δ/σ)max < 0.001
160 parameters	Δρmax = 0.15 e Å^−3
2 restraints	Δρmin = −0.16 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
N1	0.45687 (11)	0.2218 (7)	0.2697 (3)	0.0473 (8)
C1	0.54425 (12)	0.2407 (8)	0.3273 (3)	0.0427 (8)
C9	0.37076 (12)	0.2616 (9)	0.2071 (3)	0.0457 (9)
H9A	0.3823	0.3718	0.1360	0.055*
C6	0.57995 (14)	0.1614 (9)	0.4188 (3)	0.0559 (10)
H6A	0.5694	0.0602	0.4924	0.067*
C8	0.40534 (12)	0.1480 (8)	0.2952 (3)	0.0451 (8)
C7	0.49124 (12)	0.1608 (8)	0.3501 (3)	0.0460 (9)
H7A	0.4821	0.0624	0.4254	0.055*
C3	0.61133 (14)	0.4649 (10)	0.2017 (3)	0.0570 (11)
H3A	0.6223	0.5715	0.1294	0.068*
C2	0.56072 (13)	0.3894 (9)	0.2167 (3)	0.0468 (9)
C12	0.33597 (14)	−0.0682 (10)	0.4162 (4)	0.0601 (10)
H12A	0.3245	−0.1800	0.4869	0.072*
C10	0.31905 (13)	0.2118 (9)	0.2243 (3)	0.0510 (10)
C11	0.30193 (13)	0.0476 (9)	0.3297 (3)	0.0572 (11)
H11A	0.2674	0.0157	0.3421	0.069*
C14	0.28378 (13)	0.3427 (10)	0.1343 (4)	0.0585 (10)
O1	0.52789 (11)	0.4688 (8)	0.1250 (3)	0.0683 (8)
C5	0.63050 (14)	0.2312 (10)	0.4013 (4)	0.0629 (11)
H5A	0.6540	0.1756	0.4622	0.076*
C4	0.64585 (14)	0.3839 (10)	0.2928 (4)	0.0632 (11)
H4A	0.6800	0.4331	0.2808	0.076*
C13	0.38733 (13)	−0.0193 (10)	0.3986 (3)	0.0542 (10)
H13A	0.4101	−0.1006	0.4575	0.065*
N2	0.25591 (14)	0.4542 (10)	0.0648 (4)	0.0896 (13)
H1B	0.4999 (10)	0.396 (12)	0.145 (7)	0.13 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0426 (18)	0.0517 (18)	0.0474 (16)	0.0006 (13)	−0.0038 (14)	−0.0007 (13)
C1	0.038 (2)	0.0449 (17)	0.045 (2)	0.0021 (14)	0.0015 (17)	−0.0035 (16)
C9	0.042 (2)	0.048 (2)	0.046 (2)	0.0029 (16)	0.0022 (17)	−0.0027 (17)
C6	0.053 (2)	0.058 (2)	0.057 (2)	0.0006 (18)	−0.005 (2)	0.0031 (19)
C8	0.0392 (19)	0.0456 (19)	0.051 (2)	−0.0018 (15)	0.0032 (17)	−0.0088 (17)
C7	0.052 (2)	0.0445 (19)	0.042 (2)	0.0000 (16)	0.0045 (17)	0.0015 (17)
C3	0.054 (3)	0.061 (3)	0.056 (2)	−0.0065 (18)	0.0091 (19)	−0.0002 (19)
C2	0.047 (2)	0.051 (2)	0.042 (2)	−0.0009 (16)	0.0012 (16)	−0.0012 (18)
C12	0.056 (2)	0.065 (3)	0.060 (2)	−0.0083 (19)	0.006 (2)	0.006 (2)
C10	0.042 (2)	0.054 (2)	0.057 (2)	0.0035 (17)	0.0024 (19)	−0.0148 (19)
C11	0.0399 (19)	0.061 (2)	0.071 (3)	−0.0074 (17)	0.0068 (19)	−0.013 (2)
C14	0.044 (2)	0.065 (3)	0.067 (2)	0.0038 (18)	−0.006 (2)	−0.011 (2)
O1	0.0590 (17)	0.092 (2)	0.0540 (15)	−0.0015 (16)	−0.0059 (17)	0.0190 (16)
C5	0.049 (2)	0.070 (3)	0.070 (3)	0.007 (2)	−0.011 (2)	0.002 (2)
C4	0.047 (2)	0.064 (2)	0.079 (3)	−0.0066 (19)	0.004 (2)	−0.008 (2)
C13	0.047 (2)	0.060 (2)	0.056 (2)	−0.0005 (17)	0.0015 (18)	0.007 (2)
N2	0.066 (2)	0.097 (3)	0.105 (3)	0.012 (2)	−0.032 (2)	−0.004 (2)

Geometric parameters (Å, º)

N1—C7	1.277 (4)	C3—H3A	0.9300
N1—C8	1.418 (4)	C2—O1	1.351 (4)
C1—C2	1.396 (4)	C12—C11	1.372 (5)
C1—C6	1.398 (5)	C12—C13	1.382 (5)
C1—C7	1.455 (4)	C12—H12A	0.9300
C9—C8	1.390 (4)	C10—C11	1.381 (5)
C9—C10	1.391 (4)	C10—C14	1.439 (5)
C9—H9A	0.9300	C11—H11A	0.9300
C6—C5	1.375 (5)	C14—N2	1.137 (5)
C6—H6A	0.9300	O1—H1B	0.82 (2)
C8—C13	1.377 (5)	C5—C4	1.374 (5)
C7—H7A	0.9300	C5—H5A	0.9300
C3—C4	1.376 (5)	C4—H4A	0.9300
C3—C2	1.378 (4)	C13—H13A	0.9300
C7—N1—C8	120.8 (3)	C3—C2—C1	119.5 (3)
C2—C1—C6	119.0 (3)	C11—C12—C13	120.2 (3)
C2—C1—C7	122.2 (3)	C11—C12—H12A	119.9
C6—C1—C7	118.8 (3)	C13—C12—H12A	119.9
C8—C9—C10	120.5 (3)	C11—C10—C9	119.8 (3)
C8—C9—H9A	119.7	C11—C10—C14	120.6 (3)
C10—C9—H9A	119.7	C9—C10—C14	119.6 (4)
C5—C6—C1	120.9 (4)	C12—C11—C10	119.9 (3)
C5—C6—H6A	119.6	C12—C11—H11A	120.1
C1—C6—H6A	119.6	C10—C11—H11A	120.1
C13—C8—C9	118.6 (3)	N2—C14—C10	178.2 (5)
C13—C8—N1	125.8 (3)	C2—O1—H1B	108 (5)
C9—C8—N1	115.6 (3)	C4—C5—C6	119.3 (4)
N1—C7—C1	121.9 (3)	C4—C5—H5A	120.4
N1—C7—H7A	119.0	C6—C5—H5A	120.4
C1—C7—H7A	119.0	C3—C4—C5	120.8 (3)
C4—C3—C2	120.5 (4)	C3—C4—H4A	119.6
C4—C3—H3A	119.7	C5—C4—H4A	119.6
C2—C3—H3A	119.7	C12—C13—C8	121.0 (3)
O1—C2—C3	119.1 (3)	C12—C13—H13A	119.5
O1—C2—C1	121.4 (3)	C8—C13—H13A	119.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···N1	0.82 (2)	1.89 (4)	2.623 (4)	149 (7)