5-Chloro-N-(2-hydroxy-5-methyl­phenyl)­salicyl­ald­imine

The title compound, N-(5-chloro-2-oxido­benzyl­idene)-2-hydroxy-5-methyl­anilinium, C₁₄H₁₂ClNO₂, is a tridentate Schiff base with almost planar molecules. Each mol­ecule contains a strong intramolecular N—H...O hydrogen bond [2.576 (2) Å]. There is also an intermolecular O—H...O hydrogen bond [2.695 (2) Å] linking neighbouring mol­ecules into infinite chains along the [101] direction.

Computing details

Data collection: CAD-4 Diffractometer Control Software (Enraf-Nonius, 1993); cell refinement: CAD-4 Diffractometer Control Software; data reduction: X-RED (Stoe & Cie, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C14H12ClNO2	F(000) = 544
Mr = 261.70	Dx = 1.462 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.966 (3) Å	Cell parameters from 25 reflections
b = 13.392 (2) Å	θ = 3.0–15.2°
c = 14.898 (3) Å	µ = 0.31 mm^−1
β = 93.01 (2)°	T = 303 K
V = 1188.6 (7) Å^3	Prism, orange
Z = 4	0.55 × 0.25 × 0.23 mm

Data collection

Nonius CAD4 diffractometer	Rint = 0.012
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 2.1°
Graphite monochromator	h = −7→7
ω/2θ scans	k = −16→0
4649 measured reflections	l = −18→18
2331 independent reflections	3 standard reflections every 120 min
2069 reflections with I > 2σ(I)	intensity decay: 4.7%

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Calculated w = 1/[σ^2(Fo^2) + (0.063P)^2 + 0.4009P] where P = (Fo^2 + 2Fc^2)/3
2331 reflections	(Δ/σ)max = 0.002
197 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.40 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.8085 (2)	0.19468 (11)	0.23099 (9)	0.0287 (3)
C2	1.0110 (3)	0.16617 (13)	0.27922 (10)	0.0347 (4)
H2	1.046 (3)	0.1995 (14)	0.3357 (14)	0.042*
C3	1.1444 (3)	0.09169 (13)	0.24947 (11)	0.0358 (4)
H3	1.284 (3)	0.0725 (15)	0.2832 (13)	0.043*
C4	1.0847 (3)	0.04033 (12)	0.17018 (11)	0.0336 (3)
C5	0.8929 (3)	0.06511 (13)	0.12031 (10)	0.0340 (3)
H5	0.859 (3)	0.0317 (14)	0.0660 (14)	0.041*
C6	0.7536 (2)	0.14262 (12)	0.14911 (9)	0.0293 (3)
C7	0.5615 (2)	0.16998 (12)	0.09308 (10)	0.0308 (3)
H7	0.533 (3)	0.1340 (14)	0.0388 (13)	0.037*
C8	0.2344 (2)	0.28099 (11)	0.06966 (9)	0.0270 (3)
C9	0.1628 (2)	0.25504 (11)	−0.01796 (9)	0.0277 (3)
C10	−0.0352 (2)	0.29815 (13)	−0.05427 (10)	0.0342 (3)
H10	−0.084 (3)	0.2792 (14)	−0.1154 (13)	0.041*
C11	−0.1558 (3)	0.36544 (13)	−0.00581 (11)	0.0364 (4)
H11	−0.292 (3)	0.3964 (15)	−0.0333 (13)	0.044*
C12	−0.0858 (2)	0.39311 (12)	0.08108 (10)	0.0331 (3)
C13	0.1103 (2)	0.34971 (12)	0.11741 (10)	0.0315 (3)
H13	0.158 (3)	0.3654 (14)	0.1760 (13)	0.038*
C14	−0.2186 (3)	0.46653 (15)	0.13273 (14)	0.0451 (4)
H14A	−0.184 (4)	0.5292 (19)	0.1209 (15)	0.054*
H14B	−0.189 (4)	0.4607 (16)	0.1953 (17)	0.054*
H14C	−0.368 (4)	0.4502 (16)	0.1303 (15)	0.054*
N1	0.4295 (2)	0.24208 (10)	0.11578 (8)	0.0290 (3)
H1N	0.479 (3)	0.2684 (14)	0.1696 (13)	0.035*
O1	0.68096 (17)	0.26534 (9)	0.26019 (7)	0.0355 (3)
O2	0.28311 (18)	0.18971 (9)	−0.06613 (7)	0.0361 (3)
H2O	0.2440	0.1942	−0.1196	0.043*
Cl1	1.26096 (7)	−0.05462 (4)	0.13498 (3)	0.04943 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0218 (7)	0.0384 (8)	0.0256 (7)	−0.0038 (6)	−0.0020 (5)	0.0046 (6)
C2	0.0268 (7)	0.0471 (9)	0.0289 (7)	−0.0017 (6)	−0.0091 (6)	−0.0004 (6)
C3	0.0246 (7)	0.0480 (9)	0.0337 (8)	0.0008 (6)	−0.0089 (6)	0.0049 (7)
C4	0.0277 (7)	0.0382 (8)	0.0345 (8)	0.0025 (6)	−0.0017 (6)	0.0037 (6)
C5	0.0303 (8)	0.0423 (9)	0.0287 (8)	0.0004 (6)	−0.0056 (6)	−0.0008 (6)
C6	0.0224 (7)	0.0387 (8)	0.0262 (7)	−0.0028 (6)	−0.0047 (5)	0.0041 (6)
C7	0.0251 (7)	0.0406 (8)	0.0260 (7)	−0.0019 (6)	−0.0046 (5)	0.0012 (6)
C8	0.0191 (6)	0.0346 (7)	0.0270 (7)	−0.0033 (5)	−0.0026 (5)	0.0041 (5)
C9	0.0214 (7)	0.0345 (7)	0.0269 (7)	−0.0009 (5)	−0.0011 (5)	0.0022 (6)
C10	0.0265 (7)	0.0454 (9)	0.0298 (8)	0.0023 (6)	−0.0071 (6)	0.0012 (6)
C11	0.0257 (7)	0.0434 (9)	0.0394 (8)	0.0052 (6)	−0.0048 (6)	0.0048 (7)
C12	0.0266 (7)	0.0332 (8)	0.0398 (8)	−0.0007 (6)	0.0037 (6)	0.0013 (6)
C13	0.0281 (7)	0.0374 (8)	0.0286 (7)	−0.0038 (6)	−0.0008 (6)	−0.0020 (6)
C14	0.0385 (10)	0.0407 (10)	0.0566 (12)	0.0030 (8)	0.0082 (8)	−0.0062 (8)
N1	0.0210 (6)	0.0417 (7)	0.0238 (6)	−0.0027 (5)	−0.0049 (5)	0.0009 (5)
O1	0.0288 (5)	0.0492 (7)	0.0277 (5)	0.0040 (5)	−0.0052 (4)	−0.0032 (5)
O2	0.0320 (6)	0.0516 (7)	0.0240 (5)	0.0108 (5)	−0.0058 (4)	−0.0032 (5)
Cl1	0.0454 (3)	0.0539 (3)	0.0481 (3)	0.01850 (19)	−0.00622 (19)	−0.00399 (19)

Geometric parameters (Å, º)

C1—O1	1.3033 (18)	C8—N1	1.4189 (18)
C1—C2	1.425 (2)	C9—O2	1.3602 (18)
C1—C6	1.428 (2)	C9—C10	1.398 (2)
C2—C3	1.364 (2)	C10—C11	1.381 (2)
C2—H2	0.97 (2)	C10—H10	0.975 (19)
C3—C4	1.397 (2)	C11—C12	1.390 (2)
C3—H3	0.98 (2)	C11—H11	0.98 (2)
C4—C5	1.372 (2)	C12—C13	1.390 (2)
C4—Cl1	1.7479 (17)	C12—C14	1.500 (2)
C5—C6	1.411 (2)	C13—H13	0.928 (19)
C5—H5	0.94 (2)	C14—H14A	0.88 (2)
C6—C7	1.430 (2)	C14—H14B	0.94 (2)
C7—N1	1.302 (2)	C14—H14C	0.91 (2)
C7—H7	0.949 (19)	N1—H1N	0.910 (19)
C8—C9	1.396 (2)	O2—H2O	0.8200
C8—C13	1.399 (2)
O1—C1—C2	121.37 (13)	O2—C9—C10	121.34 (13)
O1—C1—C6	121.86 (12)	C8—C9—C10	118.05 (14)
C2—C1—C6	116.77 (14)	C11—C10—C9	121.36 (14)
C3—C2—C1	121.71 (14)	C11—C10—H10	121.3 (11)
C3—C2—H2	121.1 (12)	C9—C10—H10	117.4 (11)
C1—C2—H2	117.1 (12)	C10—C11—C12	121.44 (14)
C2—C3—C4	120.50 (14)	C10—C11—H11	120.0 (11)
C2—C3—H3	121.2 (11)	C12—C11—H11	118.6 (11)
C4—C3—H3	118.3 (11)	C11—C12—C13	117.19 (14)
C5—C4—C3	120.48 (15)	C11—C12—C14	120.77 (15)
C5—C4—Cl1	120.75 (13)	C13—C12—C14	122.04 (15)
C3—C4—Cl1	118.77 (12)	C12—C13—C8	122.28 (14)
C4—C5—C6	120.08 (14)	C12—C13—H13	118.9 (12)
C4—C5—H5	119.2 (12)	C8—C13—H13	118.8 (12)
C6—C5—H5	120.6 (12)	C12—C14—H14A	112.8 (15)
C5—C6—C1	120.44 (13)	C12—C14—H14B	112.2 (13)
C5—C6—C7	118.55 (14)	H14A—C14—H14B	104.1 (19)
C1—C6—C7	120.97 (14)	C12—C14—H14C	111.2 (14)
N1—C7—C6	121.05 (14)	H14A—C14—H14C	117 (2)
N1—C7—H7	121.1 (11)	H14B—C14—H14C	98.6 (19)
C6—C7—H7	117.9 (11)	C7—N1—C8	129.67 (13)
C9—C8—C13	119.67 (13)	C7—N1—H1N	110.2 (12)
C9—C8—N1	124.37 (13)	C8—N1—H1N	120.1 (12)
C13—C8—N1	115.96 (13)	C9—O2—H2O	109.5
O2—C9—C8	120.61 (12)
O1—C1—C2—C3	179.44 (14)	N1—C8—C9—O2	−1.1 (2)
C6—C1—C2—C3	−1.0 (2)	C13—C8—C9—C10	−1.1 (2)
C1—C2—C3—C4	−0.4 (2)	N1—C8—C9—C10	178.91 (13)
C2—C3—C4—C5	1.0 (2)	O2—C9—C10—C11	−179.17 (14)
C2—C3—C4—Cl1	−179.90 (13)	C8—C9—C10—C11	0.8 (2)
C3—C4—C5—C6	−0.3 (2)	C9—C10—C11—C12	0.0 (3)
Cl1—C4—C5—C6	−179.33 (12)	C10—C11—C12—C13	−0.4 (2)
C4—C5—C6—C1	−1.1 (2)	C10—C11—C12—C14	179.84 (16)
C4—C5—C6—C7	176.71 (14)	C11—C12—C13—C8	0.0 (2)
O1—C1—C6—C5	−178.71 (13)	C14—C12—C13—C8	179.81 (15)
C2—C1—C6—C5	1.7 (2)	C9—C8—C13—C12	0.7 (2)
O1—C1—C6—C7	3.5 (2)	N1—C8—C13—C12	−179.29 (13)
C2—C1—C6—C7	−176.05 (14)	C6—C7—N1—C8	179.20 (13)
C5—C6—C7—N1	−178.87 (14)	C9—C8—N1—C7	−8.7 (2)
C1—C6—C7—N1	−1.0 (2)	C13—C8—N1—C7	171.37 (15)
C13—C8—C9—O2	178.84 (13)