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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101000993/fr1313sup1.cif
Contains datablocks I, last

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101000993/fr1313Isup2.hkl
Contains datablock I

CCDC reference: 163944

Computing details top

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) top
Crystal data top
C14H12ClNO2F(000) = 544
Mr = 261.70Dx = 1.462 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 5.966 (3) ÅCell parameters from 25 reflections
b = 13.392 (2) Åθ = 3.0–15.2°
c = 14.898 (3) ŵ = 0.31 mm1
β = 93.01 (2)°T = 303 K
V = 1188.6 (7) Å3Prism, orange
Z = 40.55 × 0.25 × 0.23 mm
Data collection top
Nonius CAD4
diffractometer
Rint = 0.012
Radiation source: fine-focus sealed tubeθmax = 26.0°, θmin = 2.1°
Graphite monochromatorh = 77
ω/2θ scansk = 160
4649 measured reflectionsl = 1818
2331 independent reflections3 standard reflections every 120 min
2069 reflections with I > 2σ(I) intensity decay: 4.7%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H atoms treated by a mixture of independent and constrained refinement
S = 1.07Calculated w = 1/[σ2(Fo2) + (0.063P)2 + 0.4009P]
where P = (Fo2 + 2Fc2)/3
2331 reflections(Δ/σ)max = 0.002
197 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.40 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.8085 (2)0.19468 (11)0.23099 (9)0.0287 (3)
C21.0110 (3)0.16617 (13)0.27922 (10)0.0347 (4)
H21.046 (3)0.1995 (14)0.3357 (14)0.042*
C31.1444 (3)0.09169 (13)0.24947 (11)0.0358 (4)
H31.284 (3)0.0725 (15)0.2832 (13)0.043*
C41.0847 (3)0.04033 (12)0.17018 (11)0.0336 (3)
C50.8929 (3)0.06511 (13)0.12031 (10)0.0340 (3)
H50.859 (3)0.0317 (14)0.0660 (14)0.041*
C60.7536 (2)0.14262 (12)0.14911 (9)0.0293 (3)
C70.5615 (2)0.16998 (12)0.09308 (10)0.0308 (3)
H70.533 (3)0.1340 (14)0.0388 (13)0.037*
C80.2344 (2)0.28099 (11)0.06966 (9)0.0270 (3)
C90.1628 (2)0.25504 (11)0.01796 (9)0.0277 (3)
C100.0352 (2)0.29815 (13)0.05427 (10)0.0342 (3)
H100.084 (3)0.2792 (14)0.1154 (13)0.041*
C110.1558 (3)0.36544 (13)0.00581 (11)0.0364 (4)
H110.292 (3)0.3964 (15)0.0333 (13)0.044*
C120.0858 (2)0.39311 (12)0.08108 (10)0.0331 (3)
C130.1103 (2)0.34971 (12)0.11741 (10)0.0315 (3)
H130.158 (3)0.3654 (14)0.1760 (13)0.038*
C140.2186 (3)0.46653 (15)0.13273 (14)0.0451 (4)
H14A0.184 (4)0.5292 (19)0.1209 (15)0.054*
H14B0.189 (4)0.4607 (16)0.1953 (17)0.054*
H14C0.368 (4)0.4502 (16)0.1303 (15)0.054*
N10.4295 (2)0.24208 (10)0.11578 (8)0.0290 (3)
H1N0.479 (3)0.2684 (14)0.1696 (13)0.035*
O10.68096 (17)0.26534 (9)0.26019 (7)0.0355 (3)
O20.28311 (18)0.18971 (9)0.06613 (7)0.0361 (3)
H2O0.24400.19420.11960.043*
Cl11.26096 (7)0.05462 (4)0.13498 (3)0.04943 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0218 (7)0.0384 (8)0.0256 (7)0.0038 (6)0.0020 (5)0.0046 (6)
C20.0268 (7)0.0471 (9)0.0289 (7)0.0017 (6)0.0091 (6)0.0004 (6)
C30.0246 (7)0.0480 (9)0.0337 (8)0.0008 (6)0.0089 (6)0.0049 (7)
C40.0277 (7)0.0382 (8)0.0345 (8)0.0025 (6)0.0017 (6)0.0037 (6)
C50.0303 (8)0.0423 (9)0.0287 (8)0.0004 (6)0.0056 (6)0.0008 (6)
C60.0224 (7)0.0387 (8)0.0262 (7)0.0028 (6)0.0047 (5)0.0041 (6)
C70.0251 (7)0.0406 (8)0.0260 (7)0.0019 (6)0.0046 (5)0.0012 (6)
C80.0191 (6)0.0346 (7)0.0270 (7)0.0033 (5)0.0026 (5)0.0041 (5)
C90.0214 (7)0.0345 (7)0.0269 (7)0.0009 (5)0.0011 (5)0.0022 (6)
C100.0265 (7)0.0454 (9)0.0298 (8)0.0023 (6)0.0071 (6)0.0012 (6)
C110.0257 (7)0.0434 (9)0.0394 (8)0.0052 (6)0.0048 (6)0.0048 (7)
C120.0266 (7)0.0332 (8)0.0398 (8)0.0007 (6)0.0037 (6)0.0013 (6)
C130.0281 (7)0.0374 (8)0.0286 (7)0.0038 (6)0.0008 (6)0.0020 (6)
C140.0385 (10)0.0407 (10)0.0566 (12)0.0030 (8)0.0082 (8)0.0062 (8)
N10.0210 (6)0.0417 (7)0.0238 (6)0.0027 (5)0.0049 (5)0.0009 (5)
O10.0288 (5)0.0492 (7)0.0277 (5)0.0040 (5)0.0052 (4)0.0032 (5)
O20.0320 (6)0.0516 (7)0.0240 (5)0.0108 (5)0.0058 (4)0.0032 (5)
Cl10.0454 (3)0.0539 (3)0.0481 (3)0.01850 (19)0.00622 (19)0.00399 (19)
Geometric parameters (Å, º) top
C1—O11.3033 (18)C8—N11.4189 (18)
C1—C21.425 (2)C9—O21.3602 (18)
C1—C61.428 (2)C9—C101.398 (2)
C2—C31.364 (2)C10—C111.381 (2)
C2—H20.97 (2)C10—H100.975 (19)
C3—C41.397 (2)C11—C121.390 (2)
C3—H30.98 (2)C11—H110.98 (2)
C4—C51.372 (2)C12—C131.390 (2)
C4—Cl11.7479 (17)C12—C141.500 (2)
C5—C61.411 (2)C13—H130.928 (19)
C5—H50.94 (2)C14—H14A0.88 (2)
C6—C71.430 (2)C14—H14B0.94 (2)
C7—N11.302 (2)C14—H14C0.91 (2)
C7—H70.949 (19)N1—H1N0.910 (19)
C8—C91.396 (2)O2—H2O0.8200
C8—C131.399 (2)
O1—C1—C2121.37 (13)O2—C9—C10121.34 (13)
O1—C1—C6121.86 (12)C8—C9—C10118.05 (14)
C2—C1—C6116.77 (14)C11—C10—C9121.36 (14)
C3—C2—C1121.71 (14)C11—C10—H10121.3 (11)
C3—C2—H2121.1 (12)C9—C10—H10117.4 (11)
C1—C2—H2117.1 (12)C10—C11—C12121.44 (14)
C2—C3—C4120.50 (14)C10—C11—H11120.0 (11)
C2—C3—H3121.2 (11)C12—C11—H11118.6 (11)
C4—C3—H3118.3 (11)C11—C12—C13117.19 (14)
C5—C4—C3120.48 (15)C11—C12—C14120.77 (15)
C5—C4—Cl1120.75 (13)C13—C12—C14122.04 (15)
C3—C4—Cl1118.77 (12)C12—C13—C8122.28 (14)
C4—C5—C6120.08 (14)C12—C13—H13118.9 (12)
C4—C5—H5119.2 (12)C8—C13—H13118.8 (12)
C6—C5—H5120.6 (12)C12—C14—H14A112.8 (15)
C5—C6—C1120.44 (13)C12—C14—H14B112.2 (13)
C5—C6—C7118.55 (14)H14A—C14—H14B104.1 (19)
C1—C6—C7120.97 (14)C12—C14—H14C111.2 (14)
N1—C7—C6121.05 (14)H14A—C14—H14C117 (2)
N1—C7—H7121.1 (11)H14B—C14—H14C98.6 (19)
C6—C7—H7117.9 (11)C7—N1—C8129.67 (13)
C9—C8—C13119.67 (13)C7—N1—H1N110.2 (12)
C9—C8—N1124.37 (13)C8—N1—H1N120.1 (12)
C13—C8—N1115.96 (13)C9—O2—H2O109.5
O2—C9—C8120.61 (12)
O1—C1—C2—C3179.44 (14)N1—C8—C9—O21.1 (2)
C6—C1—C2—C31.0 (2)C13—C8—C9—C101.1 (2)
C1—C2—C3—C40.4 (2)N1—C8—C9—C10178.91 (13)
C2—C3—C4—C51.0 (2)O2—C9—C10—C11179.17 (14)
C2—C3—C4—Cl1179.90 (13)C8—C9—C10—C110.8 (2)
C3—C4—C5—C60.3 (2)C9—C10—C11—C120.0 (3)
Cl1—C4—C5—C6179.33 (12)C10—C11—C12—C130.4 (2)
C4—C5—C6—C11.1 (2)C10—C11—C12—C14179.84 (16)
C4—C5—C6—C7176.71 (14)C11—C12—C13—C80.0 (2)
O1—C1—C6—C5178.71 (13)C14—C12—C13—C8179.81 (15)
C2—C1—C6—C51.7 (2)C9—C8—C13—C120.7 (2)
O1—C1—C6—C73.5 (2)N1—C8—C13—C12179.29 (13)
C2—C1—C6—C7176.05 (14)C6—C7—N1—C8179.20 (13)
C5—C6—C7—N1178.87 (14)C9—C8—N1—C78.7 (2)
C1—C6—C7—N11.0 (2)C13—C8—N1—C7171.37 (15)
C13—C8—C9—O2178.84 (13)
 

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