The title compound, C
19H
15ClN
2O, a tridentate Schiff base, has been synthesized and structurally characterized by IR spectroscopy and X-ray structure analysis. The hydroxy and imino groups are involved in a resonance-assisted O—H
N hydrogen bond with O
N = 2.517 (2) Å. Intermolecular O—H
N and N—H
O hydrogen bonds create centrosymmetric dimers in the crystal packing.
Supporting information
CCDC reference: 618259
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.134
- Data-to-parameter ratio = 16.7
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT073_ALERT_1_A H-atoms ref, but _hydrogen_treatment reported as constr
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
0 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).
2-[(2-Aminophenylimino)(phenyl)methyl]-4-chlorophenol
top
Crystal data top
C19H15ClN2O | Z = 2 |
Mr = 322.78 | F(000) = 336 |
Triclinic, P1 | Dx = 1.306 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.5630 (17) Å | Cell parameters from 25 reflections |
b = 9.4940 (19) Å | θ = 1.0–27.0° |
c = 11.069 (2) Å | µ = 0.24 mm−1 |
α = 68.96 (3)° | T = 293 K |
β = 84.84 (3)° | Block, orange-red |
γ = 77.75 (3)° | 0.25 × 0.20 × 0.18 mm |
V = 820.7 (3) Å3 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.012 |
Radiation source: fine-focus sealed tube | θmax = 27.0°, θmin = 2.0° |
Graphite monochromator | h = 0→10 |
ω scans | k = −11→11 |
3790 measured reflections | l = −13→13 |
3549 independent reflections | 3 standard reflections every 100 reflections |
2455 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
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)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.134 | w = 1/[σ2(Fo2) + (0.0738P)2 + 0.1224P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3549 reflections | Δρmax = 0.26 e Å−3 |
213 parameters | Δρmin = −0.28 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.025 (5) |
Special details top
Experimental. IR (KBr, ν, cm-1): 3461, 3367, 1622, 1591, 1556, 1488, 1459, 1399, 1328,
1274, 828, 742. |
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 (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.18057 (7) | 0.20413 (7) | 0.91289 (5) | 0.0833 (2) | |
O1 | 0.80388 (15) | 0.18775 (16) | 0.64595 (14) | 0.0639 (4) | |
N1 | 0.8660 (2) | 0.00353 (19) | 0.36404 (17) | 0.0689 (5) | |
H1A | 0.9313 | −0.0653 | 0.3414 | 0.083* | |
H1B | 0.8364 | −0.0158 | 0.4438 | 0.083* | |
N2 | 0.66648 (16) | 0.22691 (16) | 0.44144 (14) | 0.0499 (4) | |
C1 | 0.6405 (2) | 0.4014 (2) | 0.21374 (18) | 0.0589 (5) | |
H1C | 0.5679 | 0.4751 | 0.2377 | 0.071* | |
C2 | 0.6902 (2) | 0.4337 (2) | 0.08618 (19) | 0.0651 (5) | |
H2B | 0.6523 | 0.5291 | 0.0244 | 0.078* | |
C3 | 0.7975 (2) | 0.3222 (3) | 0.05075 (19) | 0.0645 (5) | |
H3A | 0.8313 | 0.3437 | −0.0351 | 0.077* | |
C4 | 0.8544 (2) | 0.1800 (2) | 0.14210 (19) | 0.0598 (5) | |
H4A | 0.9243 | 0.1061 | 0.1165 | 0.072* | |
C5 | 0.80827 (19) | 0.1457 (2) | 0.27199 (17) | 0.0494 (4) | |
C6 | 0.69861 (19) | 0.2590 (2) | 0.30684 (16) | 0.0477 (4) | |
C7 | 0.52507 (19) | 0.24673 (17) | 0.49311 (15) | 0.0442 (4) | |
C8 | 0.37497 (19) | 0.28955 (18) | 0.41849 (15) | 0.0447 (4) | |
C9 | 0.3489 (2) | 0.1992 (2) | 0.34851 (17) | 0.0547 (4) | |
H9A | 0.4242 | 0.1121 | 0.3501 | 0.066* | |
C10 | 0.2112 (3) | 0.2397 (3) | 0.2771 (2) | 0.0688 (5) | |
H10A | 0.1935 | 0.1791 | 0.2317 | 0.083* | |
C11 | 0.0997 (3) | 0.3707 (3) | 0.2734 (2) | 0.0742 (6) | |
H11A | 0.0076 | 0.3978 | 0.2251 | 0.089* | |
C12 | 0.1247 (2) | 0.4611 (3) | 0.3411 (2) | 0.0690 (6) | |
H12A | 0.0501 | 0.5494 | 0.3374 | 0.083* | |
C13 | 0.2605 (2) | 0.4205 (2) | 0.41441 (18) | 0.0550 (4) | |
H13A | 0.2758 | 0.4805 | 0.4612 | 0.066* | |
C14 | 0.5173 (2) | 0.22144 (18) | 0.63330 (16) | 0.0463 (4) | |
C15 | 0.6580 (2) | 0.19452 (19) | 0.70322 (17) | 0.0516 (4) | |
C16 | 0.6472 (3) | 0.1754 (2) | 0.83422 (19) | 0.0627 (5) | |
H16A | 0.7397 | 0.1597 | 0.8791 | 0.075* | |
C17 | 0.5024 (3) | 0.1794 (2) | 0.89834 (18) | 0.0647 (5) | |
H17A | 0.4966 | 0.1680 | 0.9856 | 0.078* | |
C18 | 0.3647 (2) | 0.2006 (2) | 0.83165 (18) | 0.0581 (5) | |
C19 | 0.3710 (2) | 0.22072 (19) | 0.70174 (17) | 0.0512 (4) | |
H19A | 0.2774 | 0.2340 | 0.6590 | 0.061* | |
H1 | 0.785 (3) | 0.200 (3) | 0.560 (3) | 0.109 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0857 (4) | 0.0932 (4) | 0.0619 (3) | −0.0140 (3) | 0.0251 (3) | −0.0243 (3) |
O1 | 0.0490 (7) | 0.0760 (9) | 0.0649 (9) | 0.0067 (6) | −0.0100 (6) | −0.0308 (7) |
N1 | 0.0624 (10) | 0.0613 (10) | 0.0665 (10) | 0.0067 (8) | 0.0106 (8) | −0.0159 (8) |
N2 | 0.0467 (8) | 0.0521 (8) | 0.0472 (8) | −0.0021 (6) | −0.0008 (6) | −0.0171 (6) |
C1 | 0.0550 (10) | 0.0573 (11) | 0.0563 (10) | −0.0033 (8) | 0.0019 (8) | −0.0150 (9) |
C2 | 0.0662 (12) | 0.0663 (12) | 0.0521 (10) | −0.0128 (10) | −0.0061 (9) | −0.0065 (9) |
C3 | 0.0694 (12) | 0.0826 (14) | 0.0458 (10) | −0.0271 (11) | 0.0069 (9) | −0.0224 (10) |
C4 | 0.0574 (11) | 0.0695 (12) | 0.0603 (11) | −0.0181 (9) | 0.0129 (8) | −0.0319 (10) |
C5 | 0.0390 (8) | 0.0544 (10) | 0.0557 (10) | −0.0104 (7) | 0.0021 (7) | −0.0200 (8) |
C6 | 0.0393 (8) | 0.0560 (10) | 0.0475 (9) | −0.0083 (7) | 0.0012 (7) | −0.0185 (8) |
C7 | 0.0463 (9) | 0.0370 (8) | 0.0474 (9) | −0.0036 (6) | −0.0006 (7) | −0.0152 (7) |
C8 | 0.0454 (8) | 0.0446 (9) | 0.0413 (8) | −0.0096 (7) | 0.0025 (6) | −0.0119 (7) |
C9 | 0.0620 (11) | 0.0528 (10) | 0.0522 (10) | −0.0168 (8) | 0.0021 (8) | −0.0194 (8) |
C10 | 0.0747 (13) | 0.0784 (14) | 0.0630 (12) | −0.0339 (11) | −0.0053 (10) | −0.0246 (10) |
C11 | 0.0593 (12) | 0.0866 (16) | 0.0694 (13) | −0.0214 (11) | −0.0156 (10) | −0.0109 (12) |
C12 | 0.0527 (11) | 0.0665 (13) | 0.0752 (13) | −0.0005 (9) | −0.0068 (9) | −0.0146 (11) |
C13 | 0.0511 (10) | 0.0521 (10) | 0.0588 (10) | −0.0024 (8) | −0.0030 (8) | −0.0195 (8) |
C14 | 0.0519 (9) | 0.0377 (8) | 0.0465 (9) | −0.0011 (7) | −0.0029 (7) | −0.0153 (7) |
C15 | 0.0557 (10) | 0.0424 (9) | 0.0544 (10) | 0.0046 (7) | −0.0085 (8) | −0.0200 (8) |
C16 | 0.0714 (13) | 0.0589 (11) | 0.0548 (11) | 0.0048 (9) | −0.0166 (9) | −0.0223 (9) |
C17 | 0.0902 (15) | 0.0551 (11) | 0.0434 (9) | −0.0005 (10) | −0.0051 (10) | −0.0174 (8) |
C18 | 0.0704 (12) | 0.0490 (10) | 0.0494 (10) | −0.0058 (8) | 0.0093 (9) | −0.0162 (8) |
C19 | 0.0548 (10) | 0.0487 (9) | 0.0489 (9) | −0.0074 (7) | 0.0016 (7) | −0.0177 (7) |
Geometric parameters (Å, º) top
Cl1—C18 | 1.743 (2) | C8—C13 | 1.400 (2) |
O1—C15 | 1.348 (2) | C8—C9 | 1.405 (2) |
O1—H1 | 0.95 (3) | C9—C10 | 1.386 (3) |
N1—C5 | 1.387 (2) | C9—H9A | 0.9300 |
N1—H1A | 0.8600 | C10—C11 | 1.388 (3) |
N1—H1B | 0.8600 | C10—H10A | 0.9300 |
N2—C7 | 1.298 (2) | C11—C12 | 1.384 (3) |
N2—C6 | 1.423 (2) | C11—H11A | 0.9300 |
C1—C2 | 1.380 (3) | C12—C13 | 1.383 (3) |
C1—C6 | 1.395 (3) | C12—H12A | 0.9300 |
C1—H1C | 0.9300 | C13—H13A | 0.9300 |
C2—C3 | 1.392 (3) | C14—C19 | 1.404 (2) |
C2—H2B | 0.9300 | C14—C15 | 1.419 (2) |
C3—C4 | 1.383 (3) | C15—C16 | 1.392 (3) |
C3—H3A | 0.9300 | C16—C17 | 1.372 (3) |
C4—C5 | 1.395 (3) | C16—H16A | 0.9300 |
C4—H4A | 0.9300 | C17—C18 | 1.387 (3) |
C5—C6 | 1.411 (2) | C17—H17A | 0.9300 |
C7—C14 | 1.480 (2) | C18—C19 | 1.378 (3) |
C7—C8 | 1.493 (2) | C19—H19A | 0.9300 |
| | | |
C15—O1—H1 | 104.7 (18) | C8—C9—H9A | 119.9 |
C5—N1—H1A | 120.0 | C9—C10—C11 | 120.0 (2) |
C5—N1—H1B | 120.0 | C9—C10—H10A | 120.0 |
H1A—N1—H1B | 120.0 | C11—C10—H10A | 120.0 |
C7—N2—C6 | 124.91 (14) | C12—C11—C10 | 120.39 (19) |
C2—C1—C6 | 120.31 (18) | C12—C11—H11A | 119.8 |
C2—C1—H1C | 119.8 | C10—C11—H11A | 119.8 |
C6—C1—H1C | 119.8 | C13—C12—C11 | 120.1 (2) |
C1—C2—C3 | 119.53 (19) | C13—C12—H12A | 119.9 |
C1—C2—H2B | 120.2 | C11—C12—H12A | 119.9 |
C3—C2—H2B | 120.2 | C12—C13—C8 | 120.29 (18) |
C4—C3—C2 | 120.59 (18) | C12—C13—H13A | 119.9 |
C4—C3—H3A | 119.7 | C8—C13—H13A | 119.9 |
C2—C3—H3A | 119.7 | C19—C14—C15 | 117.89 (15) |
C3—C4—C5 | 120.97 (18) | C19—C14—C7 | 121.19 (15) |
C3—C4—H4A | 119.5 | C15—C14—C7 | 120.91 (15) |
C5—C4—H4A | 119.5 | O1—C15—C16 | 118.46 (16) |
N1—C5—C4 | 121.14 (16) | O1—C15—C14 | 121.71 (15) |
N1—C5—C6 | 120.83 (16) | C16—C15—C14 | 119.83 (17) |
C4—C5—C6 | 118.02 (17) | C17—C16—C15 | 121.22 (18) |
C1—C6—C5 | 120.56 (16) | C17—C16—H16A | 119.4 |
C1—C6—N2 | 122.37 (15) | C15—C16—H16A | 119.4 |
C5—C6—N2 | 116.67 (15) | C16—C17—C18 | 119.29 (17) |
N2—C7—C14 | 116.77 (15) | C16—C17—H17A | 120.4 |
N2—C7—C8 | 123.04 (14) | C18—C17—H17A | 120.4 |
C14—C7—C8 | 120.18 (14) | C19—C18—C17 | 120.99 (18) |
C13—C8—C9 | 119.08 (16) | C19—C18—Cl1 | 119.50 (16) |
C13—C8—C7 | 121.18 (15) | C17—C18—Cl1 | 119.51 (15) |
C9—C8—C7 | 119.72 (15) | C18—C19—C14 | 120.71 (18) |
C10—C9—C8 | 120.11 (19) | C18—C19—H19A | 119.6 |
C10—C9—H9A | 119.9 | C14—C19—H19A | 119.6 |
| | | |
C6—C1—C2—C3 | 0.7 (3) | C9—C10—C11—C12 | −0.3 (3) |
C1—C2—C3—C4 | 0.0 (3) | C10—C11—C12—C13 | −0.8 (3) |
C2—C3—C4—C5 | −1.3 (3) | C11—C12—C13—C8 | 1.3 (3) |
C3—C4—C5—N1 | −179.50 (18) | C9—C8—C13—C12 | −0.8 (3) |
C3—C4—C5—C6 | 1.7 (3) | C7—C8—C13—C12 | 177.80 (17) |
C2—C1—C6—C5 | −0.3 (3) | N2—C7—C14—C19 | −171.85 (15) |
C2—C1—C6—N2 | 172.16 (17) | C8—C7—C14—C19 | 6.9 (2) |
N1—C5—C6—C1 | −179.72 (17) | N2—C7—C14—C15 | 7.1 (2) |
C4—C5—C6—C1 | −0.9 (3) | C8—C7—C14—C15 | −174.21 (14) |
N1—C5—C6—N2 | 7.4 (2) | C19—C14—C15—O1 | 177.57 (15) |
C4—C5—C6—N2 | −173.77 (15) | C7—C14—C15—O1 | −1.4 (2) |
C7—N2—C6—C1 | 53.3 (2) | C19—C14—C15—C16 | −2.9 (2) |
C7—N2—C6—C5 | −133.98 (17) | C7—C14—C15—C16 | 178.16 (16) |
C6—N2—C7—C14 | −174.07 (15) | O1—C15—C16—C17 | −179.26 (17) |
C6—N2—C7—C8 | 7.2 (3) | C14—C15—C16—C17 | 1.2 (3) |
N2—C7—C8—C13 | −124.09 (18) | C15—C16—C17—C18 | 0.9 (3) |
C14—C7—C8—C13 | 57.3 (2) | C16—C17—C18—C19 | −1.3 (3) |
N2—C7—C8—C9 | 54.5 (2) | C16—C17—C18—Cl1 | 179.48 (15) |
C14—C7—C8—C9 | −124.16 (17) | C17—C18—C19—C14 | −0.5 (3) |
C13—C8—C9—C10 | −0.3 (3) | Cl1—C18—C19—C14 | 178.73 (13) |
C7—C8—C9—C10 | −178.85 (16) | C15—C14—C19—C18 | 2.5 (2) |
C8—C9—C10—C11 | 0.8 (3) | C7—C14—C19—C18 | −178.50 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.86 | 2.31 | 3.035 (2) | 142 |
O1—H1···N2 | 0.95 (3) | 1.64 (3) | 2.517 (2) | 153 (3) |
Symmetry code: (i) −x+2, −y, −z+1. |