Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807058898/hg2350sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807058898/hg2350Isup2.hkl |
CCDC reference: 673044
A mixture of 1,2,4-triazole 0.90 g (0.013 mol), 2,2-bis(2,6-dichlorostyryl)oxirane 3.86 g (0.01 mol) dissolved in DMF and powdered potassium carbonate 0.1 g was stirred vigorously at gentle reflux for 2 h (Graham et al., 1985). The reaction mixture was cooled, then concentrated by removing the solvent under reduced pressure·The residue was taken up in water. The solid residue was then recrystallized from ethanol to give 3-((1H-1,2,4-triazol-1-yl)methyl)-1,5-bis(2,6-dichlorophenyl) penta-1,4-dien-3-ol 3.64 g(yield 80%). Single crystals suitable for X-ray measurement were obtained by recrystallization from methanol at room temperature.
All H atoms were found on difference maps. The hydroxyl H atoms were refined freely, giving an O—H bond distance of 0.74 Å. The remaining H atoms were placed in calculated positions, with C—H = 0.95 or 0.99 Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2 times Ueq(C).
Data collection: RAPID-AUTO (Rigaku 2004); cell refinement: RAPID-AUTO (Rigaku 2004); data reduction: RAPID-AUTO (Rigaku 2004); 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.
C20H15Cl4N3O | F(000) = 928 |
Mr = 455.15 | Dx = 1.535 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1494 reflections |
a = 8.3413 (17) Å | θ = 2.6–26.4° |
b = 10.652 (2) Å | µ = 0.62 mm−1 |
c = 22.229 (4) Å | T = 153 K |
β = 94.32 (3)° | Block, colorless |
V = 1969.5 (7) Å3 | 0.32 × 0.22 × 0.16 mm |
Z = 4 |
Rigaku RAXIS RAPID IP area-detector diffractometer | 3470 independent reflections |
Radiation source: Rotating Anode | 2901 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω Oscillation scans | θmax = 25.0°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi 1995) | h = −9→9 |
Tmin = 0.827, Tmax = 0.908 | k = −12→11 |
15134 measured reflections | l = −26→26 |
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)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.085 | w = 1/[σ2(Fo2) + (0.0359P)2 + 0.8502P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
3470 reflections | Δρmax = 0.27 e Å−3 |
258 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0048 (6) |
C20H15Cl4N3O | V = 1969.5 (7) Å3 |
Mr = 455.15 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.3413 (17) Å | µ = 0.62 mm−1 |
b = 10.652 (2) Å | T = 153 K |
c = 22.229 (4) Å | 0.32 × 0.22 × 0.16 mm |
β = 94.32 (3)° |
Rigaku RAXIS RAPID IP area-detector diffractometer | 3470 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi 1995) | 2901 reflections with I > 2σ(I) |
Tmin = 0.827, Tmax = 0.908 | Rint = 0.031 |
15134 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.085 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.27 e Å−3 |
3470 reflections | Δρmin = −0.22 e Å−3 |
258 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 | ||
Cl4 | 0.43666 (7) | 0.42402 (6) | 0.34867 (3) | 0.06239 (19) | |
Cl2 | 0.33568 (7) | 0.22308 (5) | 0.23550 (3) | 0.05817 (18) | |
Cl3 | 0.85225 (8) | 0.35813 (5) | 0.54500 (3) | 0.0637 (2) | |
Cl1 | 0.23987 (7) | −0.25254 (6) | 0.31663 (3) | 0.0666 (2) | |
O1 | 0.64236 (17) | −0.00926 (13) | 0.42224 (7) | 0.0441 (4) | |
N1 | 0.98450 (18) | 0.03373 (14) | 0.38889 (7) | 0.0387 (4) | |
C13 | 0.2879 (2) | −0.01739 (17) | 0.27484 (8) | 0.0351 (4) | |
C6 | 0.6561 (2) | 0.39721 (17) | 0.44453 (8) | 0.0348 (4) | |
N2 | 1.0809 (2) | 0.13526 (15) | 0.38301 (8) | 0.0473 (4) | |
C10 | 0.8402 (2) | 0.01560 (19) | 0.34845 (9) | 0.0433 (5) | |
H10A | 0.8277 | −0.0752 | 0.3397 | 0.052* | |
H10B | 0.8554 | 0.0587 | 0.3098 | 0.052* | |
C9 | 0.6840 (2) | 0.06435 (16) | 0.37317 (8) | 0.0348 (4) | |
C11 | 0.5554 (2) | 0.05100 (18) | 0.32121 (8) | 0.0384 (4) | |
H11A | 0.5765 | 0.0882 | 0.2838 | 0.046* | |
C15 | 0.0685 (2) | −0.1425 (2) | 0.22533 (9) | 0.0471 (5) | |
H15A | 0.0088 | −0.2185 | 0.2234 | 0.057* | |
N3 | 1.1824 (2) | 0.00913 (18) | 0.45797 (8) | 0.0521 (5) | |
C12 | 0.4179 (2) | −0.00754 (18) | 0.32389 (8) | 0.0383 (4) | |
H12A | 0.3998 | −0.0477 | 0.3609 | 0.046* | |
C8 | 0.6932 (2) | 0.20331 (16) | 0.38717 (8) | 0.0352 (4) | |
H8A | 0.7318 | 0.2559 | 0.3569 | 0.042* | |
C14 | 0.1950 (2) | −0.12640 (19) | 0.26875 (8) | 0.0400 (4) | |
C4 | 0.7604 (3) | 0.58210 (19) | 0.50010 (9) | 0.0500 (5) | |
H4A | 0.8260 | 0.6162 | 0.5329 | 0.060* | |
C1 | 0.5691 (2) | 0.48093 (18) | 0.40644 (9) | 0.0414 (4) | |
C5 | 0.7486 (2) | 0.45377 (18) | 0.49228 (8) | 0.0397 (4) | |
C17 | 0.1171 (2) | 0.0629 (2) | 0.18888 (9) | 0.0495 (5) | |
H17A | 0.0916 | 0.1289 | 0.1610 | 0.059* | |
C20 | 1.1960 (2) | 0.1150 (2) | 0.42536 (9) | 0.0475 (5) | |
H20A | 1.2836 | 0.1714 | 0.4327 | 0.057* | |
C18 | 0.2413 (2) | 0.07738 (18) | 0.23329 (9) | 0.0404 (4) | |
C7 | 0.6534 (2) | 0.25908 (17) | 0.43680 (8) | 0.0367 (4) | |
H7A | 0.6215 | 0.2085 | 0.4690 | 0.044* | |
C19 | 1.0475 (2) | −0.0394 (2) | 0.43300 (9) | 0.0477 (5) | |
H19A | 1.0018 | −0.1163 | 0.4450 | 0.057* | |
C2 | 0.5793 (3) | 0.60988 (19) | 0.41337 (9) | 0.0473 (5) | |
H2B | 0.5191 | 0.6636 | 0.3860 | 0.057* | |
C16 | 0.0304 (2) | −0.0475 (2) | 0.18522 (9) | 0.0525 (6) | |
H16A | −0.0554 | −0.0576 | 0.1550 | 0.063* | |
C3 | 0.6762 (3) | 0.65986 (19) | 0.45980 (10) | 0.0508 (5) | |
H3B | 0.6852 | 0.7484 | 0.4641 | 0.061* | |
H1A | 0.686 (3) | 0.006 (2) | 0.4516 (11) | 0.050 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl4 | 0.0641 (4) | 0.0592 (3) | 0.0593 (3) | 0.0088 (3) | −0.0255 (3) | −0.0059 (3) |
Cl2 | 0.0587 (3) | 0.0427 (3) | 0.0695 (4) | 0.0006 (2) | −0.0191 (3) | 0.0066 (2) |
Cl3 | 0.0799 (4) | 0.0533 (3) | 0.0535 (3) | 0.0072 (3) | −0.0249 (3) | 0.0025 (3) |
Cl1 | 0.0618 (4) | 0.0589 (4) | 0.0756 (4) | −0.0161 (3) | −0.0185 (3) | 0.0215 (3) |
O1 | 0.0496 (8) | 0.0393 (7) | 0.0408 (8) | −0.0077 (6) | −0.0145 (7) | 0.0034 (6) |
N1 | 0.0343 (8) | 0.0369 (8) | 0.0433 (9) | 0.0072 (7) | −0.0084 (7) | −0.0077 (7) |
C13 | 0.0291 (9) | 0.0435 (10) | 0.0321 (9) | 0.0039 (8) | −0.0022 (7) | −0.0061 (8) |
C6 | 0.0360 (9) | 0.0345 (9) | 0.0342 (9) | 0.0006 (8) | 0.0053 (8) | −0.0016 (8) |
N2 | 0.0450 (9) | 0.0413 (9) | 0.0542 (10) | 0.0001 (8) | −0.0055 (8) | −0.0035 (8) |
C10 | 0.0387 (10) | 0.0443 (11) | 0.0445 (11) | 0.0073 (8) | −0.0133 (9) | −0.0144 (9) |
C9 | 0.0341 (9) | 0.0330 (9) | 0.0355 (9) | 0.0016 (7) | −0.0090 (8) | −0.0011 (7) |
C11 | 0.0366 (10) | 0.0428 (10) | 0.0345 (10) | 0.0046 (8) | −0.0067 (8) | −0.0006 (8) |
C15 | 0.0343 (10) | 0.0568 (13) | 0.0492 (12) | −0.0051 (9) | −0.0040 (9) | −0.0114 (10) |
N3 | 0.0391 (9) | 0.0672 (12) | 0.0482 (10) | 0.0071 (8) | −0.0092 (8) | −0.0006 (9) |
C12 | 0.0386 (10) | 0.0405 (10) | 0.0344 (10) | 0.0043 (8) | −0.0062 (8) | −0.0037 (8) |
C8 | 0.0326 (9) | 0.0339 (9) | 0.0385 (10) | 0.0019 (8) | −0.0004 (8) | 0.0014 (8) |
C14 | 0.0334 (9) | 0.0475 (11) | 0.0385 (10) | 0.0024 (8) | −0.0015 (8) | −0.0016 (8) |
C4 | 0.0618 (13) | 0.0412 (11) | 0.0460 (12) | −0.0055 (10) | −0.0027 (10) | −0.0079 (9) |
C1 | 0.0428 (10) | 0.0421 (11) | 0.0385 (10) | 0.0021 (8) | −0.0013 (8) | −0.0025 (8) |
C5 | 0.0427 (10) | 0.0385 (10) | 0.0372 (10) | 0.0022 (8) | −0.0009 (8) | 0.0023 (8) |
C17 | 0.0425 (11) | 0.0588 (13) | 0.0447 (11) | 0.0090 (10) | −0.0127 (9) | 0.0024 (10) |
C20 | 0.0379 (10) | 0.0524 (12) | 0.0513 (12) | −0.0012 (9) | −0.0039 (9) | −0.0129 (10) |
C18 | 0.0358 (10) | 0.0420 (10) | 0.0422 (10) | 0.0034 (8) | −0.0050 (8) | −0.0037 (9) |
C7 | 0.0371 (9) | 0.0347 (9) | 0.0378 (10) | 0.0002 (8) | −0.0003 (8) | 0.0016 (8) |
C19 | 0.0417 (11) | 0.0462 (11) | 0.0536 (12) | 0.0072 (9) | −0.0062 (10) | 0.0034 (10) |
C2 | 0.0556 (12) | 0.0396 (11) | 0.0464 (11) | 0.0093 (9) | 0.0027 (10) | 0.0066 (9) |
C16 | 0.0374 (11) | 0.0726 (15) | 0.0447 (12) | 0.0037 (10) | −0.0147 (9) | −0.0085 (11) |
C3 | 0.0669 (14) | 0.0325 (10) | 0.0535 (13) | −0.0003 (10) | 0.0083 (11) | −0.0021 (9) |
Cl4—C1 | 1.739 (2) | C15—C16 | 1.370 (3) |
Cl2—C18 | 1.739 (2) | C15—C14 | 1.386 (3) |
Cl3—C5 | 1.7341 (19) | C15—H15A | 0.9500 |
Cl1—C14 | 1.737 (2) | N3—C19 | 1.322 (3) |
O1—C9 | 1.408 (2) | N3—C20 | 1.350 (3) |
O1—H1A | 0.74 (2) | C12—H12A | 0.9500 |
N1—C19 | 1.329 (2) | C8—C7 | 1.317 (3) |
N1—N2 | 1.360 (2) | C8—H8A | 0.9500 |
N1—C10 | 1.460 (2) | C4—C3 | 1.374 (3) |
C13—C14 | 1.397 (3) | C4—C5 | 1.381 (3) |
C13—C18 | 1.403 (3) | C4—H4A | 0.9500 |
C13—C12 | 1.483 (2) | C1—C2 | 1.384 (3) |
C6—C1 | 1.395 (3) | C17—C16 | 1.380 (3) |
C6—C5 | 1.400 (3) | C17—C18 | 1.385 (3) |
C6—C7 | 1.481 (2) | C17—H17A | 0.9500 |
N2—C20 | 1.311 (3) | C20—H20A | 0.9500 |
C10—C9 | 1.542 (3) | C7—H7A | 0.9500 |
C10—H10A | 0.9900 | C19—H19A | 0.9500 |
C10—H10B | 0.9900 | C2—C3 | 1.370 (3) |
C9—C8 | 1.513 (2) | C2—H2B | 0.9500 |
C9—C11 | 1.523 (2) | C16—H16A | 0.9500 |
C11—C12 | 1.310 (3) | C3—H3B | 0.9500 |
C11—H11A | 0.9500 | ||
C9—O1—H1A | 115.4 (19) | C15—C14—C13 | 123.92 (18) |
C19—N1—N2 | 109.47 (15) | C15—C14—Cl1 | 116.65 (16) |
C19—N1—C10 | 129.67 (17) | C13—C14—Cl1 | 119.42 (14) |
N2—N1—C10 | 120.81 (16) | C3—C4—C5 | 119.11 (19) |
C14—C13—C18 | 114.21 (16) | C3—C4—H4A | 120.4 |
C14—C13—C12 | 119.99 (16) | C5—C4—H4A | 120.4 |
C18—C13—C12 | 125.74 (17) | C2—C1—C6 | 122.84 (18) |
C1—C6—C5 | 114.62 (17) | C2—C1—Cl4 | 117.28 (15) |
C1—C6—C7 | 124.18 (16) | C6—C1—Cl4 | 119.86 (15) |
C5—C6—C7 | 121.20 (16) | C4—C5—C6 | 123.48 (18) |
C20—N2—N1 | 101.93 (16) | C4—C5—Cl3 | 117.98 (15) |
N1—C10—C9 | 114.57 (15) | C6—C5—Cl3 | 118.53 (15) |
N1—C10—H10A | 108.6 | C16—C17—C18 | 119.83 (19) |
C9—C10—H10A | 108.6 | C16—C17—H17A | 120.1 |
N1—C10—H10B | 108.6 | C18—C17—H17A | 120.1 |
C9—C10—H10B | 108.6 | N2—C20—N3 | 115.85 (18) |
H10A—C10—H10B | 107.6 | N2—C20—H20A | 122.1 |
O1—C9—C8 | 113.39 (15) | N3—C20—H20A | 122.1 |
O1—C9—C11 | 109.57 (15) | C17—C18—C13 | 122.98 (18) |
C8—C9—C11 | 105.62 (14) | C17—C18—Cl2 | 115.59 (15) |
O1—C9—C10 | 110.66 (15) | C13—C18—Cl2 | 121.41 (14) |
C8—C9—C10 | 111.81 (15) | C8—C7—C6 | 122.85 (17) |
C11—C9—C10 | 105.33 (15) | C8—C7—H7A | 118.6 |
C12—C11—C9 | 125.37 (18) | C6—C7—H7A | 118.6 |
C12—C11—H11A | 117.3 | N3—C19—N1 | 110.91 (19) |
C9—C11—H11A | 117.3 | N3—C19—H19A | 124.5 |
C16—C15—C14 | 119.26 (19) | N1—C19—H19A | 124.5 |
C16—C15—H15A | 120.4 | C3—C2—C1 | 119.81 (19) |
C14—C15—H15A | 120.4 | C3—C2—H2B | 120.1 |
C19—N3—C20 | 101.83 (17) | C1—C2—H2B | 120.1 |
C11—C12—C13 | 126.46 (18) | C15—C16—C17 | 119.77 (17) |
C11—C12—H12A | 116.8 | C15—C16—H16A | 120.1 |
C13—C12—H12A | 116.8 | C17—C16—H16A | 120.1 |
C7—C8—C9 | 126.96 (17) | C2—C3—C4 | 120.05 (19) |
C7—C8—H8A | 116.5 | C2—C3—H3B | 120.0 |
C9—C8—H8A | 116.5 | C4—C3—H3B | 120.0 |
C19—N1—N2—C20 | −0.5 (2) | C3—C4—C5—C6 | 0.9 (3) |
C10—N1—N2—C20 | −178.22 (16) | C3—C4—C5—Cl3 | −178.38 (17) |
C19—N1—C10—C9 | 87.3 (2) | C1—C6—C5—C4 | −3.0 (3) |
N2—N1—C10—C9 | −95.5 (2) | C7—C6—C5—C4 | 177.26 (19) |
N1—C10—C9—O1 | −68.6 (2) | C1—C6—C5—Cl3 | 176.25 (14) |
N1—C10—C9—C8 | 58.8 (2) | C7—C6—C5—Cl3 | −3.5 (3) |
N1—C10—C9—C11 | 173.04 (16) | N1—N2—C20—N3 | 0.1 (2) |
O1—C9—C11—C12 | 7.5 (3) | C19—N3—C20—N2 | 0.3 (2) |
C8—C9—C11—C12 | −115.0 (2) | C16—C17—C18—C13 | 1.7 (3) |
C10—C9—C11—C12 | 126.6 (2) | C16—C17—C18—Cl2 | −177.19 (17) |
C9—C11—C12—C13 | 177.26 (17) | C14—C13—C18—C17 | −1.8 (3) |
C14—C13—C12—C11 | 145.6 (2) | C12—C13—C18—C17 | −179.10 (19) |
C18—C13—C12—C11 | −37.2 (3) | C14—C13—C18—Cl2 | 177.03 (14) |
O1—C9—C8—C7 | −6.4 (2) | C12—C13—C18—Cl2 | −0.2 (3) |
C11—C9—C8—C7 | 113.6 (2) | C9—C8—C7—C6 | −175.63 (16) |
C10—C9—C8—C7 | −132.37 (19) | C1—C6—C7—C8 | 57.6 (3) |
C16—C15—C14—C13 | 0.4 (3) | C5—C6—C7—C8 | −122.7 (2) |
C16—C15—C14—Cl1 | −178.21 (16) | C20—N3—C19—N1 | −0.7 (2) |
C18—C13—C14—C15 | 0.8 (3) | N2—N1—C19—N3 | 0.8 (2) |
C12—C13—C14—C15 | 178.21 (18) | C10—N1—C19—N3 | 178.20 (18) |
C18—C13—C14—Cl1 | 179.34 (14) | C6—C1—C2—C3 | −1.0 (3) |
C12—C13—C14—Cl1 | −3.2 (2) | Cl4—C1—C2—C3 | 177.09 (17) |
C5—C6—C1—C2 | 3.0 (3) | C14—C15—C16—C17 | −0.6 (3) |
C7—C6—C1—C2 | −177.25 (19) | C18—C17—C16—C15 | −0.4 (3) |
C5—C6—C1—Cl4 | −174.96 (14) | C1—C2—C3—C4 | −1.4 (3) |
C7—C6—C1—Cl4 | 4.7 (3) | C5—C4—C3—C2 | 1.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N3i | 0.74 (2) | 2.22 (2) | 2.940 (2) | 163 (2) |
Symmetry code: (i) −x+2, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C20H15Cl4N3O |
Mr | 455.15 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 153 |
a, b, c (Å) | 8.3413 (17), 10.652 (2), 22.229 (4) |
β (°) | 94.32 (3) |
V (Å3) | 1969.5 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.62 |
Crystal size (mm) | 0.32 × 0.22 × 0.16 |
Data collection | |
Diffractometer | Rigaku RAXIS RAPID IP area-detector diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi 1995) |
Tmin, Tmax | 0.827, 0.908 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15134, 3470, 2901 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.085, 1.06 |
No. of reflections | 3470 |
No. of parameters | 258 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.22 |
Computer programs: RAPID-AUTO (Rigaku 2004), SHELXTL (Sheldrick, 2001), SHELXTL (Sheldrick, 2001.
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N3i | 0.74 (2) | 2.22 (2) | 2.940 (2) | 163 (2) |
Symmetry code: (i) −x+2, −y, −z+1. |
Derivatives of 1,2,4-triazole are known to exhibit diverse applications in the fields of medicine, agriculture and industry. Among the agriculture profiles of various 1,2,4-triazole and its derivatives, their fungicidal, bactericidal, pesticidal and plant growth properties (Massa et al., 1992) seem to be the most widely documented. For these reasons, the structures of substituted 1,2,4-triazole have been a subject of interest in our laboratory. The crystal structure of the title compound is presented here.
The bond lengths and angles are normal for this type of compound (Rong et al., 2006). The dihedral angles formed by phenyl ring (C1 - C6) and phenyl ring (C13 –C18) with plane (N1/N2/N3/C19/C20) are 34.20 (2) and 10.10 (2)°, respectively. The dihedral angle between the benzene rings is 24.41 (3)°. The molecules assemble to form helical superstructures along the b axis. The helic pitch is 10.65 (2) Å. The right-handed and left-handed helix associate through weak hydrogen bonds, which further assemble along c axis to form two-dimensional layer structure through O—H···N hydrogen bonds.