4-[(4-Chloro­benzyl­idene)­amino]­phenol

In the molecular structure of the title Schiff base, C₁₃H₁₀ClNO, the chloro­phenyl ring and form­imidoyl moiety are almost coplanar, and the dihedral angle between the planes of the phenol and chloro­phenyl ring is 34.57 (9)°. The crystal structure is stabilized by intermolecular O—H...N hydrogen bonds, forming an infinite one-dimensional chain extending in the b direction, with an O...N distance of 2.846 (2) Å.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.063
• wR factor = 0.193
• Data-to-parameter ratio = 17.6

checkCIF/PLATON results

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Computing details

Data collection: MSC/AFC Diffractomer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractomer Control Software; data reduction: TEXSAN (Molecular Structure Corporation,1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

4-[(4-chlorobenzylidene)-amino]-phenol

Crystal data

C13H10ClNO	Dx = 1.380 Mg m^−3
Mr = 231.67	Mo Kα radiation, λ = 0.71069 Å
Orthorhombic, Pbca	Cell parameters from 25 reflections
a = 16.866 (3) Å	θ = 20.6–24.2°
b = 12.704 (5) Å	µ = 0.32 mm^−1
c = 10.410 (2) Å	T = 293 K
V = 2230.6 (10) Å^3	Prismatic, yellow
Z = 8	0.40 × 0.38 × 0.30 mm
F(000) = 960

Data collection

Rigaku AFC-7S diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 30.0°, θmin = 2.4°
Graphite monochromator	h = 0→23
ω/2θ scans	k = 0→17
3250 measured reflections	l = 0→14
3250 independent reflections	3 standard reflections every 150 reflections
2209 reflections with I > 2σ(I)	intensity decay: 0.5%

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.193	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0975P)^2 + 0.6308P] where P = (Fo^2 + 2Fc^2)/3
3250 reflections	(Δ/σ)max = 0.005
185 parameters	Δρmax = 0.76 e Å^−3
0 restraints	Δρmin = −0.60 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
Cl1	0.38455 (4)	0.93228 (5)	0.16354 (8)	0.0780 (3)
N1	0.63405 (9)	0.58122 (11)	−0.11516 (15)	0.0412 (3)
O1	0.80338 (10)	0.23262 (11)	−0.28930 (14)	0.0549 (4)
C1	0.76179 (10)	0.31491 (12)	−0.23989 (18)	0.0421 (4)
C2	0.72864 (12)	0.38553 (14)	−0.32672 (16)	0.0440 (4)
C3	0.68722 (12)	0.47236 (13)	−0.28280 (17)	0.0435 (4)
C4	0.67652 (10)	0.48927 (12)	−0.15165 (16)	0.0391 (4)
C5	0.70966 (11)	0.41764 (13)	−0.06484 (17)	0.0418 (4)
C6	0.75225 (10)	0.33153 (13)	−0.10876 (17)	0.0416 (4)
C7	0.59178 (11)	0.57966 (14)	−0.01360 (19)	0.0432 (4)
C8	0.54422 (10)	0.66934 (13)	0.03053 (17)	0.0407 (4)
C9	0.54219 (12)	0.76471 (16)	−0.0355 (2)	0.0516 (4)
C10	0.49398 (15)	0.84590 (18)	0.0060 (2)	0.0604 (5)
C11	0.44741 (11)	0.83150 (16)	0.1139 (2)	0.0504 (4)
C12	0.44841 (12)	0.73825 (19)	0.1809 (2)	0.0545 (5)
C13	0.49705 (12)	0.65748 (16)	0.13874 (19)	0.0501 (4)
H1	0.820 (2)	0.195 (3)	−0.230 (3)	0.089 (10)*
H2	0.7347 (12)	0.3741 (18)	−0.416 (2)	0.045 (5)*
H3	0.6622 (14)	0.5227 (18)	−0.344 (2)	0.045 (6)*
H5	0.7055 (13)	0.4309 (16)	0.025 (2)	0.046 (6)*
H6	0.7796 (14)	0.2840 (19)	−0.047 (2)	0.059 (6)*
H7	0.5882 (15)	0.521 (2)	0.038 (2)	0.054 (6)*
H9	0.5708 (18)	0.775 (2)	−0.110 (3)	0.081 (8)*
H10	0.4900 (18)	0.911 (2)	−0.043 (3)	0.072 (8)*
H12	0.4162 (15)	0.7293 (19)	0.250 (2)	0.058 (6)*
H13	0.4987 (17)	0.591 (2)	0.186 (2)	0.062 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0740 (4)	0.0685 (4)	0.0915 (5)	0.0255 (3)	0.0163 (3)	−0.0143 (3)
N1	0.0440 (7)	0.0330 (6)	0.0467 (8)	0.0002 (5)	0.0003 (6)	−0.0022 (5)
O1	0.0730 (10)	0.0423 (7)	0.0494 (7)	0.0158 (6)	0.0072 (6)	0.0009 (6)
C1	0.0475 (8)	0.0327 (7)	0.0460 (8)	0.0006 (6)	0.0032 (7)	−0.0004 (6)
C2	0.0572 (10)	0.0368 (8)	0.0379 (8)	0.0029 (7)	0.0055 (7)	0.0027 (6)
C3	0.0527 (9)	0.0360 (8)	0.0417 (8)	0.0026 (7)	0.0008 (7)	0.0053 (6)
C4	0.0419 (8)	0.0309 (7)	0.0445 (8)	−0.0008 (6)	0.0019 (6)	0.0001 (6)
C5	0.0468 (9)	0.0391 (8)	0.0395 (8)	−0.0005 (6)	−0.0018 (6)	−0.0007 (6)
C6	0.0453 (8)	0.0357 (7)	0.0439 (8)	0.0012 (6)	−0.0016 (7)	0.0049 (6)
C7	0.0417 (8)	0.0375 (8)	0.0505 (9)	−0.0005 (6)	−0.0004 (7)	−0.0002 (7)
C8	0.0387 (8)	0.0394 (8)	0.0440 (8)	−0.0006 (6)	−0.0008 (6)	−0.0058 (6)
C9	0.0556 (10)	0.0462 (10)	0.0529 (10)	0.0081 (8)	0.0087 (8)	0.0035 (8)
C10	0.0676 (13)	0.0478 (10)	0.0660 (12)	0.0127 (9)	0.0108 (10)	0.0042 (9)
C11	0.0449 (9)	0.0502 (10)	0.0562 (10)	0.0074 (7)	0.0005 (8)	−0.0121 (8)
C12	0.0449 (9)	0.0639 (12)	0.0547 (10)	0.0009 (9)	0.0109 (8)	−0.0018 (9)
C13	0.0488 (9)	0.0464 (9)	0.0551 (10)	−0.0001 (8)	0.0060 (8)	0.0023 (8)

Geometric parameters (Å, º)

Cl1—C11	1.741 (2)	C6—H6	0.99 (3)
N1—C7	1.275 (2)	C7—C8	1.467 (2)
N1—C4	1.422 (2)	C7—H7	0.92 (3)
O1—C1	1.360 (2)	C8—C13	1.387 (2)
O1—H1	0.83 (4)	C8—C9	1.394 (3)
C1—C6	1.391 (3)	C9—C10	1.382 (3)
C1—C2	1.391 (2)	C9—H9	0.92 (3)
C2—C3	1.383 (3)	C10—C11	1.383 (3)
C2—H2	0.94 (2)	C10—H10	0.97 (3)
C3—C4	1.394 (2)	C11—C12	1.375 (3)
C3—H3	1.00 (2)	C12—C13	1.385 (3)
C4—C5	1.399 (2)	C12—H12	0.91 (3)
C5—C6	1.386 (2)	C13—H13	0.98 (3)
C5—H5	0.95 (2)
C7—N1—C4	119.4 (2)	N1—C7—H7	122.1 (15)
C1—O1—H1	110 (2)	C8—C7—H7	114.3 (15)
O1—C1—C6	123.2 (2)	C13—C8—C9	118.74 (17)
O1—C1—C2	117.2 (2)	C13—C8—C7	118.91 (17)
C6—C1—C2	119.57 (15)	C9—C8—C7	122.3 (2)
C3—C2—C1	120.17 (16)	C10—C9—C8	120.60 (19)
C3—C2—H2	120.2 (14)	C10—C9—H9	117.6 (18)
C1—C2—H2	119.7 (14)	C8—C9—H9	121.7 (18)
C2—C3—C4	120.80 (16)	C11—C10—C9	119.3 (2)
C2—C3—H3	121.0 (13)	C11—C10—H10	120.1 (17)
C4—C3—H3	118.2 (13)	C9—C10—H10	120.5 (17)
C3—C4—C5	118.73 (16)	C12—C11—C10	121.28 (18)
C3—C4—N1	116.97 (15)	C12—C11—Cl1	119.4 (2)
C5—C4—N1	124.3 (2)	C10—C11—Cl1	119.31 (17)
C6—C5—C4	120.48 (16)	C11—C12—C13	119.01 (18)
C6—C5—H5	120.1 (13)	C11—C12—H12	120.1 (16)
C4—C5—H5	119.3 (13)	C13—C12—H12	120.8 (16)
C5—C6—C1	120.23 (15)	C12—C13—C8	121.10 (19)
C5—C6—H6	120.5 (14)	C12—C13—H13	119.6 (16)
C1—C6—H6	119.2 (14)	C8—C13—H13	119.3 (16)
N1—C7—C8	123.6 (2)
O1—C1—C2—C3	−178.45 (17)	N1—C7—C8—C13	176.64 (18)
C6—C1—C2—C3	0.7 (3)	N1—C7—C8—C9	−0.6 (3)
C1—C2—C3—C4	−1.4 (3)	C13—C8—C9—C10	−0.1 (3)
C2—C3—C4—C5	1.1 (3)	C7—C8—C9—C10	177.17 (19)
C2—C3—C4—N1	179.24 (16)	C8—C9—C10—C11	−0.2 (4)
C7—N1—C4—C3	148.14 (18)	C9—C10—C11—C12	0.2 (4)
C7—N1—C4—C5	−33.8 (3)	C9—C10—C11—Cl1	−178.14 (18)
C3—C4—C5—C6	−0.1 (3)	C10—C11—C12—C13	−0.1 (3)
N1—C4—C5—C6	−178.05 (16)	Cl1—C11—C12—C13	178.30 (16)
C4—C5—C6—C1	−0.6 (3)	C11—C12—C13—C8	−0.1 (3)
O1—C1—C6—C5	179.43 (16)	C9—C8—C13—C12	0.2 (3)
C2—C1—C6—C5	0.3 (3)	C7—C8—C13—C12	−177.11 (18)
C4—N1—C7—C8	−178.41 (16)