X-ray and computational structural study of (E)-2-(4-chloro-phenyl-imino-meth-yl)-4-methoxy-phenol.

In the mol-ecule of the title compound, C(14)H(12)ClNO(2), the two aromatic rings are oriented at a dihedral angle of 5.92 (7)°. An intra-molecular O-H⋯N hydrogen bond results in the formation of a nearly planar six-membered ring, which is oriented at dihedral angles of 1.55 (4) and 5.95 (4)° with respect to the phenol and chlorophenyl rings, respectively. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For related literature, see: Özek et al. (2007 ▶); Odabaşoğlu, Büyükgüngör et al. (2007 ▶); Odabaşoğlu, Arslan et al. (2007 ▶); Albayrak et al. (2005 ▶); Elerman et al. (1995 ▶). For general background, see: Friesner (2005 ▶); Liu et al. (2004 ▶).

Experimental

Crystal data

C14H12ClNO2

M = 261.70

Monoclinic,

a = 21.2642 (19) Å

b = 4.7101 (3) Å

c = 12.2175 (12) Å

β = 93.361 (8)°

V = 1221.56 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.68 × 0.44 × 0.21 mm

Data collection

Stoe IPDSII diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.825, T max = 0.925

10205 measured reflections

2364 independent reflections

1789 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.099

S = 1.00

2364 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

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, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and GAUSSIAN (Frisch et al., 2004 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023416/hk2503sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023416/hk2503Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H12ClNO2	F000 = 544
Mr = 261.70	Dx = 1.423 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10205 reflections
a = 21.2642 (19) Å	θ = 1.7–27.2º
b = 4.7101 (3) Å	µ = 0.31 mm−1
c = 12.2175 (12) Å	T = 296 K
β = 93.361 (8)º	Prismatic long stick, red
V = 1221.56 (18) Å3	0.68 × 0.44 × 0.21 mm
Z = 4

Stoe IPDSII diffractometer	2364 independent reflections
Radiation source: fine-focus sealed tube	1789 reflections with I > 2σ(I)
Monochromator: plane graphite	Rint = 0.080
Detector resolution: 6.67 pixels mm-1	θmax = 26.0º
T = 296 K	θmin = 1.9º
ω scans	h = −26→26
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)	k = −5→5
Tmin = 0.825, Tmax = 0.925	l = −14→14
10205 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0641P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2364 reflections	Δρmax = 0.20 e Å−3
167 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. 225 frames, detector distance = 120 mm

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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
Cl1	0.03208 (2)	1.40379 (9)	0.66121 (4)	0.06631 (18)
O1	0.26185 (6)	0.2746 (3)	0.35438 (10)	0.0677 (4)
H1	0.2404 (12)	0.393 (5)	0.394 (2)	0.112 (9)*
O2	0.42346 (6)	−0.2199 (3)	0.66813 (10)	0.0676 (4)
N1	0.21631 (6)	0.5615 (3)	0.51562 (10)	0.0455 (3)
C1	0.29911 (7)	0.2216 (3)	0.54240 (12)	0.0428 (3)
C2	0.30182 (7)	0.1541 (3)	0.43144 (12)	0.0480 (4)
C3	0.34597 (8)	−0.0395 (4)	0.39932 (13)	0.0575 (4)
H3	0.3478	−0.0841	0.3254	0.069*
C4	0.38738 (8)	−0.1674 (4)	0.47512 (14)	0.0551 (4)
H4	0.4170	−0.2964	0.4521	0.066*
C5	0.38493 (7)	−0.1042 (3)	0.58541 (13)	0.0493 (4)
C6	0.34078 (7)	0.0873 (3)	0.61831 (13)	0.0484 (3)
H6	0.3387	0.1278	0.6925	0.058*
C7	0.47390 (9)	−0.3918 (4)	0.63688 (19)	0.0753 (6)
H7A	0.5012	−0.2819	0.5936	0.090*
H7B	0.4576	−0.5499	0.5945	0.090*
H7C	0.4971	−0.4604	0.7013	0.090*
C8	0.25442 (7)	0.4252 (3)	0.58089 (12)	0.0461 (3)
H8	0.2534	0.4579	0.6558	0.055*
C9	0.17376 (7)	0.7637 (3)	0.55533 (12)	0.0436 (3)
C10	0.12943 (7)	0.8772 (3)	0.48017 (13)	0.0522 (4)
H10	0.1291	0.8199	0.4073	0.063*
C11	0.08576 (8)	1.0737 (3)	0.51122 (14)	0.0550 (4)
H11	0.0561	1.1474	0.4599	0.066*
C12	0.08649 (7)	1.1592 (3)	0.61875 (14)	0.0496 (4)
C13	0.13070 (8)	1.0524 (4)	0.69489 (14)	0.0557 (4)
H13	0.1312	1.1129	0.7674	0.067*
C14	0.17395 (7)	0.8564 (3)	0.66347 (13)	0.0531 (4)
H14	0.2037	0.7848	0.7151	0.064*

	U11	U22	U33	U12	U13	U23
Cl1	0.0617 (3)	0.0529 (2)	0.0864 (3)	0.01245 (18)	0.0222 (2)	0.0027 (2)
O1	0.0789 (8)	0.0846 (9)	0.0392 (6)	0.0278 (7)	−0.0008 (6)	−0.0003 (6)
O2	0.0658 (7)	0.0785 (8)	0.0577 (7)	0.0260 (6)	−0.0028 (6)	0.0012 (6)
N1	0.0478 (7)	0.0442 (6)	0.0448 (7)	0.0018 (5)	0.0049 (5)	−0.0012 (5)
C1	0.0448 (7)	0.0422 (7)	0.0418 (8)	−0.0002 (6)	0.0068 (6)	−0.0005 (6)
C2	0.0521 (8)	0.0535 (9)	0.0387 (8)	0.0048 (6)	0.0045 (7)	0.0015 (6)
C3	0.0654 (10)	0.0667 (10)	0.0414 (8)	0.0101 (8)	0.0104 (7)	−0.0051 (7)
C4	0.0548 (9)	0.0571 (9)	0.0545 (10)	0.0100 (7)	0.0114 (8)	−0.0039 (7)
C5	0.0484 (8)	0.0499 (8)	0.0495 (8)	0.0037 (6)	0.0014 (7)	0.0014 (7)
C6	0.0531 (8)	0.0507 (8)	0.0414 (8)	0.0036 (7)	0.0031 (7)	−0.0039 (7)
C7	0.0683 (11)	0.0716 (12)	0.0849 (14)	0.0251 (10)	−0.0049 (10)	0.0002 (10)
C8	0.0505 (8)	0.0467 (8)	0.0415 (8)	0.0019 (6)	0.0060 (7)	−0.0027 (6)
C9	0.0439 (7)	0.0406 (7)	0.0468 (8)	−0.0016 (6)	0.0061 (6)	−0.0005 (6)
C10	0.0572 (9)	0.0534 (9)	0.0458 (9)	0.0035 (7)	0.0021 (7)	−0.0005 (7)
C11	0.0535 (9)	0.0532 (9)	0.0579 (10)	0.0075 (7)	−0.0002 (7)	0.0058 (7)
C12	0.0464 (8)	0.0404 (7)	0.0632 (10)	−0.0002 (6)	0.0133 (7)	0.0026 (7)
C13	0.0614 (9)	0.0561 (9)	0.0500 (9)	0.0054 (7)	0.0074 (8)	−0.0058 (7)
C14	0.0548 (9)	0.0558 (9)	0.0482 (9)	0.0106 (7)	−0.0002 (7)	−0.0019 (7)

O1—H1	0.88 (3)	C7—H7C	0.9600
C1—C6	1.396 (2)	C8—N1	1.2763 (19)
C1—C2	1.397 (2)	C8—H8	0.9300
C1—C8	1.448 (2)	C9—C10	1.384 (2)
C2—O1	1.3554 (18)	C9—C14	1.391 (2)
C2—C3	1.382 (2)	C9—N1	1.4186 (19)
C3—C4	1.379 (2)	C10—C11	1.380 (2)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.384 (2)	C11—C12	1.373 (2)
C4—H4	0.9300	C11—H11	0.9300
C5—O2	1.3756 (18)	C12—C13	1.378 (2)
C5—C6	1.379 (2)	C12—Cl1	1.7337 (15)
C6—H6	0.9300	C13—C14	1.374 (2)
C7—O2	1.414 (2)	C13—H13	0.9300
C7—H7A	0.9600	C14—H14	0.9300
C7—H7B	0.9600
C2—O1—H1	102.0 (17)	O2—C7—H7C	109.5
C5—O2—C7	117.19 (14)	H7A—C7—H7C	109.5
C8—N1—C9	121.22 (13)	H7B—C7—H7C	109.5
C6—C1—C2	118.74 (14)	N1—C8—C1	122.35 (14)
C6—C1—C8	119.18 (13)	N1—C8—H8	118.8
C2—C1—C8	122.08 (13)	C1—C8—H8	118.8
O1—C2—C3	119.19 (14)	C10—C9—C14	118.22 (14)
O1—C2—C1	121.27 (14)	C10—C9—N1	117.10 (13)
C3—C2—C1	119.54 (14)	C14—C9—N1	124.68 (13)
C4—C3—C2	121.03 (15)	C11—C10—C9	121.32 (15)
C4—C3—H3	119.5	C11—C10—H10	119.3
C2—C3—H3	119.5	C9—C10—H10	119.3
C3—C4—C5	120.05 (15)	C12—C11—C10	119.31 (14)
C3—C4—H4	120.0	C12—C11—H11	120.3
C5—C4—H4	120.0	C10—C11—H11	120.3
O2—C5—C6	115.56 (14)	C11—C12—C13	120.51 (15)
O2—C5—C4	125.11 (15)	C11—C12—Cl1	120.72 (12)
C6—C5—C4	119.33 (14)	C13—C12—Cl1	118.77 (13)
C5—C6—C1	121.29 (14)	C14—C13—C12	119.87 (15)
C5—C6—H6	119.4	C14—C13—H13	120.1
C1—C6—H6	119.4	C12—C13—H13	120.1
O2—C7—H7A	109.5	C13—C14—C9	120.76 (14)
O2—C7—H7B	109.5	C13—C14—H14	119.6
H7A—C7—H7B	109.5	C9—C14—H14	119.6
C6—C1—C2—O1	178.95 (14)	C14—C9—C10—C11	−1.0 (2)
C8—C1—C2—O1	−0.9 (2)	N1—C9—C10—C11	179.50 (14)
C6—C1—C2—C3	−0.9 (2)	C9—C10—C11—C12	0.3 (2)
C8—C1—C2—C3	179.23 (14)	C10—C11—C12—C13	0.6 (2)
O1—C2—C3—C4	−179.82 (16)	C10—C11—C12—Cl1	−179.55 (12)
C1—C2—C3—C4	0.1 (3)	C11—C12—C13—C14	−0.8 (2)
C2—C3—C4—C5	0.4 (3)	Cl1—C12—C13—C14	179.40 (12)
C3—C4—C5—O2	179.54 (16)	C12—C13—C14—C9	0.0 (2)
C3—C4—C5—C6	0.0 (2)	C10—C9—C14—C13	0.9 (2)
O2—C5—C6—C1	179.51 (14)	N1—C9—C14—C13	−179.70 (14)
C4—C5—C6—C1	−0.9 (2)	C1—C8—N1—C9	−178.85 (13)
C2—C1—C6—C5	1.4 (2)	C10—C9—N1—C8	−172.84 (13)
C8—C1—C6—C5	−178.79 (14)	C14—C9—N1—C8	7.7 (2)
C6—C1—C8—N1	177.90 (14)	C6—C5—O2—C7	−172.96 (15)
C2—C1—C8—N1	−2.3 (2)	C4—C5—O2—C7	7.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.88 (3)	1.79 (3)	2.6210 (18)	157 (2)
C7—H7C···O2i	0.96	2.56	3.495 (2)	164

Parameters	X-RAY	AM1	PM3	HFa	DFT/B3LYPa
C8 N1	1.276 (19)	1.292	1.302	1.262	1.293
C2 O1	1.355418)	1.368	1.357	1.336	1.344
C1 C6	1.396 (2)	1.406	1.401	1.393	1.406
C1 C8	1.448 (2)	1.466	1.459	1.467	1.449
C1 C2	1.397 (2)	1.408	1.411	1.402	1.423
N1 C9	1.418 (19)	1.409	1.431	1.408	1.406
C9 C10	1.384 (2)	1.414	1.401	1.391	1.403
C12 Cl1	1.734 (15)	1.699	1.684	1.743	1.758
C5 O2	1.3756 (18)	1.385	1.386	1.355	1.371
C11 C12 Cl1	120.72 (12)	119.860	119.505	119.595	119.538
C6 C5 O2	115.56 (14)	114.847	113.926	116.374	116.232
C6 C1 C8	119.18 (13)	116.153	118.078	118.004	119.327
C9 N1 C8	121.22 (13)	121.780	122.176	120.342	121.253
C14 C9 N1	124.68 (13)	123.445	122.813	122.881	123.392
N1 C8 C1	122.35 (14)	123.800	119.635	123.408	122.250
N1 C9 C10	117.10 (13)	117.991	116.829	118.015	117.770
C8 C1 C2 O1	-0.9 (2)	-0.050	-0.030	-0.111	-0.085
C6 C5 O2 C7	-172.96 (15)	179.476	179.983	179.698	-179.874
C10 C9 N1 C8	-172.84 (13)	-149.450	179.999	62.793	-147.450
N1 C8 C1 C6	177.90 (14)	-177.484	-0.066	-179.307	-179.448
C1 C8 N1 C9	-178.85 (13)	-179.157	179.991	-178.540	-177.303

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.88 (3)	1.79 (3)	2.6210 (18)	157 (2)
C7—H7C⋯O2i	0.96	2.56	3.495 (2)	164

Symmetry code: (i) .

Table 2

Selected geometric parameters (Å, °) calculated with X-RAY, AM1, PM3, HF and DFT

Parameters	X-RAY	AM1	PM3	HFa	DFT/B3LYPa
C8—N1	1.276 (19)	1.292	1.302	1.262	1.293
C2—O1	1.355418)	1.368	1.357	1.336	1.344
C1—C6	1.396 (2)	1.406	1.401	1.393	1.406
C1—C8	1.448 (2)	1.466	1.459	1.467	1.449
C1—C2	1.397 (2)	1.408	1.411	1.402	1.423
N1—C9	1.418 (19)	1.409	1.431	1.408	1.406
C9—C10	1.384 (2)	1.414	1.401	1.391	1.403
C12—Cl1	1.734 (15)	1.699	1.684	1.743	1.758
C5—O2	1.3756 (18)	1.385	1.386	1.355	1.371
C11—C12—Cl1	120.72 (12)	119.860	119.505	119.595	119.538
C6—C5—O2	115.56 (14)	114.847	113.926	116.374	116.232
C6—C1—C8	119.18 (13)	116.153	118.078	118.004	119.327
C9—N1 —C8	121.22 (13)	121.780	122.176	120.342	121.253
C14—C9—N1	124.68 (13)	123.445	122.813	122.881	123.392
N1—C8—C1	122.35 (14)	123.800	119.635	123.408	122.250
N1—C9—C10	117.10 (13)	117.991	116.829	118.015	117.770
C8—C1—C2—O1	−0.9 (2)	−0.050	−0.030	−0.111	−0.085
C6—C5—O2—C7	−172.96 (15)	179.476	179.983	179.698	−179.874
C10—C9—N1—C8	−172.84 (13)	−149.450	179.999	62.793	−147.450
N1—C8—C1—C6	177.90 (14)	−177.484	−0.066	−179.307	−179.448
C1—C8—N1—C9	−178.85 (13)	−179.157	179.991	−178.540	−177.303

Notes: (a) 6-31G(d,p).