organic compounds
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—HO hydrogen bond [2.576 (2) Å]. There is also an intermolecular O—HO hydrogen bond [2.695 (2) Å] linking neighbouring molecules into infinite chains along the [101] direction.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101000993/fr1313sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101000993/fr1313Isup2.hkl |
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
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) Å3 | Prism, orange |
Z = 4 | 0.55 × 0.25 × 0.23 mm |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Calculated w = 1/[σ2(Fo2) + (0.063P)2 + 0.4009P] where P = (Fo2 + 2Fc2)/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 (Å2) top
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 (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
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) top
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) |