Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680704233X/hg2286sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680704233X/hg2286Isup2.hkl |
CCDC reference: 663678
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.054
- wR factor = 0.171
- Data-to-parameter ratio = 16.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C3 .. 5.76 su PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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
For related literature, see: Ai et al. (2006); Allen et al. (1987); Gilli et al. (2000).
4,6-Dichloro-2-hydroxybenzophenone was prepared via the Fries rearrangement of 3,5-dichlorophenyl benzoate. Then this ketone (26.7 g, 0.1 mol), o-phenylenediamine (10.8 g, 0.1 mol), piperidine (9.4 g, 0.11 mol), and triethylorthoformate (16 ml) were refluxed in anhydrous ethanol (100 ml) to give a red product of the mono-condensed Schiff base 2-[(2-aminophenylimino)-phenylmethyl]-4,6-dichlorophenol. The precipitated solid was collected by filtration and washed twice with hot methanol. Single crystals suitable for X-ray measurements were obtained by slow evaporation of absolute ethanol and acetic ether (2:1 v/v) at room temperature.
All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with N—H = 0.86 Å, C—H = 0.93 Å and O—H = 0.85 Å, and with Uiso(H) = 1.2Ueq(C) for the aromatic H atoms or 1.2Ueq(parent) for the other atoms. H atoms were positioned geometrically (C—H = 0.93 Å) and allowed to ride on their parent atoms with Uiso(H) = 1.2 times Ueq(C).
In the title compound, (I), (Fig. 1), the atom N2 lies in the planes of imino-phenyl and hydroxy-phenyl groups. The dihedral angle formed by the two phenyls is 43.51 (7)°. The C7═N2 (1.298 (3) Å), C7—C14 (1.475 (4) Å) and O1—C19 (1.330 (3) Å) bond lengths are shorter than normal C═N (1.32 Å), C—C (1.54 Å) and O—C (1.44 Å) bonds (Allen et al., 1987). The C14—C19 bond length (1.424 (4) Å) is longer than a normal C═C bond (1.40 Å in benzene). These differences in bond lengths are related to a resonance-assisted hydrogen bond (RAHBA) acting between molecules with conjugated multiple π bonds (Gilli et al., 2000). Intermolecular N—H···O hydrogen bonds further stabilize the crystal packing. In the related 4-chlorophenyl compound similar resonance-assisted O—H···N hydrogen bonding was reported (Ai et al., 2006).
For related literature, see: Ai et al. (2006); Allen et al. (1987); Gilli et al. (2000).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2001) and local programs.
Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. | |
Fig. 2. The packing of (I), viewed down the b axis. |
C19H14Cl2N2O | Z = 2 |
Mr = 357.22 | F(000) = 368 |
Triclinic, P1 | Dx = 1.440 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9833 (18) Å | Cell parameters from 2933 reflections |
b = 9.4191 (19) Å | θ = 2.5–26.0° |
c = 11.361 (2) Å | µ = 0.40 mm−1 |
α = 66.61 (3)° | T = 293 K |
β = 72.87 (3)° | Block, colourless |
γ = 72.38 (3)° | 0.30 × 0.20 × 0.10 mm |
V = 824.0 (4) Å3 |
Bruker SMART 1K CCD area-detector diffractometer | 3625 independent reflections |
Radiation source: fine-focus sealed tube | 2801 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.012 |
thin–slice ω scans | θmax = 27.1°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −10→11 |
Tmin = 0.901, Tmax = 0.963 | k = −11→9 |
3854 measured reflections | l = −14→14 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.171 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0797P)2 + 0.556P] where P = (Fo2 + 2Fc2)/3 |
3625 reflections | (Δ/σ)max < 0.001 |
217 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C19H14Cl2N2O | γ = 72.38 (3)° |
Mr = 357.22 | V = 824.0 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.9833 (18) Å | Mo Kα radiation |
b = 9.4191 (19) Å | µ = 0.40 mm−1 |
c = 11.361 (2) Å | T = 293 K |
α = 66.61 (3)° | 0.30 × 0.20 × 0.10 mm |
β = 72.87 (3)° |
Bruker SMART 1K CCD area-detector diffractometer | 3625 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 2801 reflections with I > 2σ(I) |
Tmin = 0.901, Tmax = 0.963 | Rint = 0.012 |
3854 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.171 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.31 e Å−3 |
3625 reflections | Δρmin = −0.30 e Å−3 |
217 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.02655 (9) | 0.32831 (12) | 0.43610 (8) | 0.0610 (3) | |
Cl2 | 0.62563 (10) | 0.17475 (13) | 0.18588 (8) | 0.0667 (3) | |
O1 | 0.7144 (2) | 0.1622 (3) | 0.4170 (2) | 0.0484 (5) | |
H1 | 0.7376 | 0.2060 | 0.4599 | 0.058* | |
N1 | 0.9269 (3) | −0.0348 (3) | 0.6999 (3) | 0.0603 (7) | |
H1A | 1.0099 | −0.1070 | 0.7198 | 0.072* | |
H1B | 0.8726 | −0.0410 | 0.6518 | 0.072* | |
N2 | 0.6616 (3) | 0.1981 (3) | 0.6334 (2) | 0.0402 (5) | |
C1 | 0.8814 (3) | 0.0902 (4) | 0.7449 (3) | 0.0465 (7) | |
C2 | 0.9686 (4) | 0.1012 (5) | 0.8227 (3) | 0.0604 (9) | |
H2B | 1.0592 | 0.0237 | 0.8426 | 0.072* | |
C3 | 0.9244 (5) | 0.2225 (5) | 0.8704 (4) | 0.0690 (11) | |
H3A | 0.9853 | 0.2263 | 0.9221 | 0.083* | |
C4 | 0.7907 (4) | 0.3402 (4) | 0.8434 (3) | 0.0585 (9) | |
H4A | 0.7613 | 0.4231 | 0.8760 | 0.070* | |
C5 | 0.7012 (4) | 0.3318 (4) | 0.7666 (3) | 0.0486 (7) | |
H5A | 0.6120 | 0.4111 | 0.7461 | 0.058* | |
C6 | 0.7427 (3) | 0.2074 (4) | 0.7199 (3) | 0.0399 (6) | |
C7 | 0.5084 (3) | 0.2380 (3) | 0.6407 (3) | 0.0374 (6) | |
C8 | 0.3940 (3) | 0.2836 (3) | 0.7510 (3) | 0.0361 (6) | |
C9 | 0.3843 (3) | 0.1752 (4) | 0.8777 (3) | 0.0430 (6) | |
H9A | 0.4420 | 0.0716 | 0.8924 | 0.052* | |
C10 | 0.2890 (4) | 0.2213 (4) | 0.9816 (3) | 0.0529 (8) | |
H10A | 0.2812 | 0.1483 | 1.0661 | 0.063* | |
C11 | 0.2051 (4) | 0.3761 (5) | 0.9603 (3) | 0.0561 (8) | |
H11A | 0.1441 | 0.4080 | 1.0308 | 0.067* | |
C12 | 0.2117 (4) | 0.4822 (4) | 0.8356 (3) | 0.0538 (8) | |
H12A | 0.1528 | 0.5854 | 0.8215 | 0.065* | |
C13 | 0.3049 (3) | 0.4373 (4) | 0.7306 (3) | 0.0469 (7) | |
H13A | 0.3083 | 0.5099 | 0.6460 | 0.056* | |
C14 | 0.4484 (3) | 0.2356 (3) | 0.5341 (3) | 0.0367 (6) | |
C15 | 0.2839 (3) | 0.2715 (4) | 0.5370 (3) | 0.0424 (6) | |
H15A | 0.2117 | 0.2914 | 0.6093 | 0.051* | |
C16 | 0.2297 (3) | 0.2773 (4) | 0.4349 (3) | 0.0444 (7) | |
C17 | 0.3345 (3) | 0.2457 (4) | 0.3270 (3) | 0.0444 (7) | |
H17A | 0.2962 | 0.2488 | 0.2582 | 0.053* | |
C18 | 0.4950 (3) | 0.2097 (4) | 0.3227 (3) | 0.0427 (6) | |
C19 | 0.5575 (3) | 0.2001 (3) | 0.4248 (3) | 0.0398 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0374 (4) | 0.0925 (7) | 0.0603 (5) | −0.0136 (4) | −0.0155 (3) | −0.0289 (5) |
Cl2 | 0.0573 (5) | 0.1012 (8) | 0.0515 (5) | −0.0093 (5) | −0.0022 (4) | −0.0475 (5) |
O1 | 0.0349 (10) | 0.0656 (14) | 0.0490 (11) | −0.0030 (9) | −0.0081 (9) | −0.0294 (10) |
N1 | 0.0488 (16) | 0.0594 (17) | 0.0722 (19) | 0.0062 (13) | −0.0190 (14) | −0.0297 (15) |
N2 | 0.0346 (12) | 0.0504 (14) | 0.0392 (12) | −0.0050 (10) | −0.0101 (9) | −0.0196 (11) |
C1 | 0.0353 (14) | 0.0550 (18) | 0.0408 (15) | −0.0114 (13) | −0.0053 (12) | −0.0077 (13) |
C2 | 0.0439 (18) | 0.069 (2) | 0.063 (2) | −0.0079 (16) | −0.0256 (16) | −0.0095 (18) |
C3 | 0.064 (2) | 0.090 (3) | 0.063 (2) | −0.032 (2) | −0.0342 (18) | −0.009 (2) |
C4 | 0.064 (2) | 0.067 (2) | 0.060 (2) | −0.0212 (17) | −0.0187 (17) | −0.0274 (17) |
C5 | 0.0432 (16) | 0.0547 (18) | 0.0518 (17) | −0.0080 (13) | −0.0137 (13) | −0.0206 (15) |
C6 | 0.0327 (13) | 0.0526 (16) | 0.0330 (13) | −0.0101 (12) | −0.0069 (11) | −0.0119 (12) |
C7 | 0.0357 (14) | 0.0412 (15) | 0.0340 (13) | −0.0052 (11) | −0.0093 (11) | −0.0117 (11) |
C8 | 0.0317 (13) | 0.0468 (15) | 0.0352 (13) | −0.0097 (11) | −0.0090 (10) | −0.0168 (12) |
C9 | 0.0442 (15) | 0.0472 (16) | 0.0425 (15) | −0.0092 (12) | −0.0128 (12) | −0.0176 (13) |
C10 | 0.0483 (17) | 0.078 (2) | 0.0351 (14) | −0.0207 (16) | −0.0063 (13) | −0.0179 (15) |
C11 | 0.0426 (17) | 0.085 (3) | 0.0525 (18) | −0.0109 (16) | −0.0032 (14) | −0.0417 (18) |
C12 | 0.0418 (16) | 0.0587 (19) | 0.069 (2) | −0.0003 (14) | −0.0115 (15) | −0.0374 (17) |
C13 | 0.0403 (15) | 0.0511 (17) | 0.0438 (15) | −0.0037 (13) | −0.0096 (12) | −0.0139 (13) |
C14 | 0.0350 (13) | 0.0438 (15) | 0.0338 (13) | −0.0083 (11) | −0.0084 (11) | −0.0144 (11) |
C15 | 0.0330 (13) | 0.0555 (17) | 0.0352 (13) | −0.0079 (12) | −0.0052 (11) | −0.0140 (13) |
C16 | 0.0350 (14) | 0.0544 (17) | 0.0448 (15) | −0.0132 (12) | −0.0115 (12) | −0.0126 (13) |
C17 | 0.0470 (16) | 0.0543 (17) | 0.0360 (14) | −0.0116 (13) | −0.0126 (12) | −0.0158 (13) |
C18 | 0.0438 (15) | 0.0499 (16) | 0.0363 (14) | −0.0092 (12) | −0.0040 (12) | −0.0198 (13) |
C19 | 0.0344 (14) | 0.0439 (15) | 0.0371 (14) | −0.0052 (11) | −0.0068 (11) | −0.0121 (12) |
Cl1—C16 | 1.738 (3) | C7—C8 | 1.487 (4) |
Cl2—C18 | 1.732 (3) | C8—C13 | 1.390 (4) |
O1—C19 | 1.330 (3) | C8—C9 | 1.391 (4) |
O1—H1 | 0.8500 | C9—C10 | 1.379 (4) |
N1—C1 | 1.370 (4) | C9—H9A | 0.9300 |
N1—H1A | 0.8600 | C10—C11 | 1.384 (5) |
N1—H1B | 0.8600 | C10—H10A | 0.9300 |
N2—C7 | 1.298 (3) | C11—C12 | 1.368 (5) |
N2—C6 | 1.426 (3) | C11—H11A | 0.9300 |
C1—C2 | 1.392 (5) | C12—C13 | 1.379 (4) |
C1—C6 | 1.407 (4) | C12—H12A | 0.9300 |
C2—C3 | 1.358 (6) | C13—H13A | 0.9300 |
C2—H2B | 0.9300 | C14—C15 | 1.405 (4) |
C3—C4 | 1.381 (5) | C14—C19 | 1.424 (4) |
C3—H3A | 0.9300 | C15—C16 | 1.362 (4) |
C4—C5 | 1.385 (4) | C15—H15A | 0.9300 |
C4—H4A | 0.9300 | C16—C17 | 1.385 (4) |
C5—C6 | 1.380 (4) | C17—C18 | 1.368 (4) |
C5—H5A | 0.9300 | C17—H17A | 0.9300 |
C7—C14 | 1.475 (4) | C18—C19 | 1.393 (4) |
C19—O1—H1 | 109.1 | C8—C9—H9A | 120.0 |
C1—N1—H1A | 120.0 | C9—C10—C11 | 120.1 (3) |
C1—N1—H1B | 120.0 | C9—C10—H10A | 120.0 |
H1A—N1—H1B | 120.0 | C11—C10—H10A | 120.0 |
C7—N2—C6 | 125.4 (2) | C12—C11—C10 | 120.1 (3) |
N1—C1—C2 | 120.4 (3) | C12—C11—H11A | 120.0 |
N1—C1—C6 | 122.1 (3) | C10—C11—H11A | 120.0 |
C2—C1—C6 | 117.4 (3) | C11—C12—C13 | 120.5 (3) |
C3—C2—C1 | 121.6 (3) | C11—C12—H12A | 119.8 |
C3—C2—H2B | 119.2 | C13—C12—H12A | 119.8 |
C1—C2—H2B | 119.2 | C12—C13—C8 | 120.0 (3) |
C2—C3—C4 | 121.2 (3) | C12—C13—H13A | 120.0 |
C2—C3—H3A | 119.4 | C8—C13—H13A | 120.0 |
C4—C3—H3A | 119.4 | C15—C14—C19 | 119.2 (2) |
C3—C4—C5 | 118.4 (3) | C15—C14—C7 | 120.8 (2) |
C3—C4—H4A | 120.8 | C19—C14—C7 | 120.0 (2) |
C5—C4—H4A | 120.8 | C16—C15—C14 | 120.5 (3) |
C6—C5—C4 | 121.0 (3) | C16—C15—H15A | 119.8 |
C6—C5—H5A | 119.5 | C14—C15—H15A | 119.8 |
C4—C5—H5A | 119.5 | C15—C16—C17 | 121.0 (3) |
C5—C6—C1 | 120.3 (3) | C15—C16—Cl1 | 120.5 (2) |
C5—C6—N2 | 123.4 (3) | C17—C16—Cl1 | 118.6 (2) |
C1—C6—N2 | 116.0 (3) | C18—C17—C16 | 119.4 (3) |
N2—C7—C14 | 117.3 (2) | C18—C17—H17A | 120.3 |
N2—C7—C8 | 123.0 (2) | C16—C17—H17A | 120.3 |
C14—C7—C8 | 119.7 (2) | C17—C18—C19 | 122.2 (3) |
C13—C8—C9 | 119.3 (3) | C17—C18—Cl2 | 119.1 (2) |
C13—C8—C7 | 120.7 (2) | C19—C18—Cl2 | 118.6 (2) |
C9—C8—C7 | 119.9 (2) | O1—C19—C18 | 120.0 (2) |
C10—C9—C8 | 120.0 (3) | O1—C19—C14 | 122.2 (2) |
C10—C9—H9A | 120.0 | C18—C19—C14 | 117.7 (2) |
N1—C1—C2—C3 | −178.9 (3) | C11—C12—C13—C8 | −0.4 (5) |
C6—C1—C2—C3 | −1.6 (5) | C9—C8—C13—C12 | 1.8 (4) |
C1—C2—C3—C4 | 0.0 (6) | C7—C8—C13—C12 | −173.3 (3) |
C2—C3—C4—C5 | 0.3 (6) | N2—C7—C14—C15 | 177.6 (3) |
C3—C4—C5—C6 | 1.2 (5) | C8—C7—C14—C15 | −1.8 (4) |
C4—C5—C6—C1 | −2.9 (5) | N2—C7—C14—C19 | −3.8 (4) |
C4—C5—C6—N2 | −175.6 (3) | C8—C7—C14—C19 | 176.8 (2) |
N1—C1—C6—C5 | −179.8 (3) | C19—C14—C15—C16 | −2.2 (4) |
C2—C1—C6—C5 | 3.1 (4) | C7—C14—C15—C16 | 176.5 (3) |
N1—C1—C6—N2 | −6.5 (4) | C14—C15—C16—C17 | 1.1 (5) |
C2—C1—C6—N2 | 176.3 (3) | C14—C15—C16—Cl1 | −177.8 (2) |
C7—N2—C6—C5 | −40.2 (4) | C15—C16—C17—C18 | −0.7 (5) |
C7—N2—C6—C1 | 146.7 (3) | Cl1—C16—C17—C18 | 178.2 (2) |
C6—N2—C7—C14 | 173.7 (2) | C16—C17—C18—C19 | 1.5 (5) |
C6—N2—C7—C8 | −6.8 (4) | C16—C17—C18—Cl2 | −178.5 (2) |
N2—C7—C8—C13 | 113.4 (3) | C17—C18—C19—O1 | 178.9 (3) |
C14—C7—C8—C13 | −67.2 (4) | Cl2—C18—C19—O1 | −1.1 (4) |
N2—C7—C8—C9 | −61.6 (4) | C17—C18—C19—C14 | −2.6 (4) |
C14—C7—C8—C9 | 117.8 (3) | Cl2—C18—C19—C14 | 177.5 (2) |
C13—C8—C9—C10 | −1.0 (4) | C15—C14—C19—O1 | −178.7 (3) |
C7—C8—C9—C10 | 174.1 (3) | C7—C14—C19—O1 | 2.7 (4) |
C8—C9—C10—C11 | −1.1 (4) | C15—C14—C19—C18 | 2.8 (4) |
C9—C10—C11—C12 | 2.4 (5) | C7—C14—C19—C18 | −175.8 (3) |
C10—C11—C12—C13 | −1.7 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.85 | 1.87 | 2.502 (3) | 130 |
N1—H1A···O1i | 0.86 | 2.53 | 3.161 (4) | 131 |
N1—H1B···N2 | 0.86 | 2.45 | 2.765 (4) | 103 |
Symmetry code: (i) −x+2, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C19H14Cl2N2O |
Mr | 357.22 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.9833 (18), 9.4191 (19), 11.361 (2) |
α, β, γ (°) | 66.61 (3), 72.87 (3), 72.38 (3) |
V (Å3) | 824.0 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.40 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART 1K CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.901, 0.963 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3854, 3625, 2801 |
Rint | 0.012 |
(sin θ/λ)max (Å−1) | 0.640 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.171, 1.13 |
No. of reflections | 3625 |
No. of parameters | 217 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.30 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2001) and local programs.
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.85 | 1.87 | 2.502 (3) | 130 |
N1—H1A···O1i | 0.86 | 2.53 | 3.161 (4) | 131 |
N1—H1B···N2 | 0.86 | 2.45 | 2.765 (4) | 103 |
Symmetry code: (i) −x+2, −y, −z+1. |
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In the title compound, (I), (Fig. 1), the atom N2 lies in the planes of imino-phenyl and hydroxy-phenyl groups. The dihedral angle formed by the two phenyls is 43.51 (7)°. The C7═N2 (1.298 (3) Å), C7—C14 (1.475 (4) Å) and O1—C19 (1.330 (3) Å) bond lengths are shorter than normal C═N (1.32 Å), C—C (1.54 Å) and O—C (1.44 Å) bonds (Allen et al., 1987). The C14—C19 bond length (1.424 (4) Å) is longer than a normal C═C bond (1.40 Å in benzene). These differences in bond lengths are related to a resonance-assisted hydrogen bond (RAHBA) acting between molecules with conjugated multiple π bonds (Gilli et al., 2000). Intermolecular N—H···O hydrogen bonds further stabilize the crystal packing. In the related 4-chlorophenyl compound similar resonance-assisted O—H···N hydrogen bonding was reported (Ai et al., 2006).