Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027340/bh6019sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027340/bh6019Isup2.hkl |
CCDC reference: 287442
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C)= 0.003 Å
- R factor = 0.047
- wR factor = 0.128
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
An anhydrous ethanol solution of 2-hydroxy-3-methoxybenzaldehyde (o-vanillin, 1.52 g, 10 mmol) was added to an anhydrous ethanol solution of 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one (4-aminoantipyrine, 2.03 g, 10 mmol) and the mixture was stirred at 350 K for 5 h under nitrogen, whereupon a yellow precipitate appeared. The product was isolated and recrystallized from ethanol, and then dried in vacuo to give pure (I) in 89% yield. Bright yellow single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.
The H atom of the hydroxy group was found in a difference map and refined with free coordinates and isotropic U parameter. Other H atoms were included in calculated positions and refined using a riding model approximation. Constrained C—H bond lengths and Uiso parameters were 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic CH, and 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl CH3.
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
C19H19N3O3 | F(000) = 1424 |
Mr = 337.37 | Dx = 1.321 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1997 reflections |
a = 27.920 (6) Å | θ = 2.8–24.2° |
b = 7.5547 (15) Å | µ = 0.09 mm−1 |
c = 16.712 (3) Å | T = 294 K |
β = 105.753 (4)° | Block, yellow |
V = 3392.6 (12) Å3 | 0.26 × 0.24 × 0.16 mm |
Z = 8 |
Bruker SMART CCD area-detector diffractometer | 3449 independent reflections |
Radiation source: fine-focus sealed tube | 2024 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ϕ and ω scans | θmax = 26.3°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −34→32 |
Tmin = 0.970, Tmax = 0.986 | k = −8→9 |
9165 measured reflections | l = −20→17 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.06P)2 + 0.5212P] where P = (Fo2 + 2Fc2)/3 |
3449 reflections | (Δ/σ)max = 0.001 |
233 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C19H19N3O3 | V = 3392.6 (12) Å3 |
Mr = 337.37 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 27.920 (6) Å | µ = 0.09 mm−1 |
b = 7.5547 (15) Å | T = 294 K |
c = 16.712 (3) Å | 0.26 × 0.24 × 0.16 mm |
β = 105.753 (4)° |
Bruker SMART CCD area-detector diffractometer | 3449 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | 2024 reflections with I > 2σ(I) |
Tmin = 0.970, Tmax = 0.986 | Rint = 0.043 |
9165 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.21 e Å−3 |
3449 reflections | Δρmin = −0.27 e Å−3 |
233 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 | ||
O1 | 0.41761 (5) | 0.56172 (17) | 0.68922 (9) | 0.0447 (4) | |
O2 | 0.56334 (6) | 0.18800 (18) | 0.57666 (9) | 0.0508 (4) | |
H2 | 0.5332 (10) | 0.197 (3) | 0.5971 (15) | 0.084 (8)* | |
O3 | 0.64031 (5) | 0.2462 (2) | 0.51859 (10) | 0.0566 (4) | |
N1 | 0.37966 (6) | 0.2932 (2) | 0.70078 (10) | 0.0378 (4) | |
N2 | 0.38624 (6) | 0.1157 (2) | 0.67788 (10) | 0.0408 (4) | |
N3 | 0.49232 (6) | 0.3105 (2) | 0.63286 (9) | 0.0353 (4) | |
C1 | 0.33016 (7) | 0.3580 (2) | 0.68750 (12) | 0.0355 (5) | |
C2 | 0.29110 (8) | 0.2895 (3) | 0.62557 (12) | 0.0460 (6) | |
H2A | 0.2963 | 0.1937 | 0.5940 | 0.055* | |
C3 | 0.24436 (9) | 0.3643 (3) | 0.61092 (14) | 0.0572 (6) | |
H3 | 0.2180 | 0.3180 | 0.5696 | 0.069* | |
C4 | 0.23651 (9) | 0.5062 (4) | 0.65685 (16) | 0.0611 (7) | |
H4 | 0.2051 | 0.5573 | 0.6460 | 0.073* | |
C5 | 0.27526 (9) | 0.5728 (3) | 0.71912 (15) | 0.0574 (7) | |
H5 | 0.2698 | 0.6687 | 0.7504 | 0.069* | |
C6 | 0.32231 (8) | 0.4983 (3) | 0.73574 (13) | 0.0439 (5) | |
H6 | 0.3482 | 0.5420 | 0.7787 | 0.053* | |
C7 | 0.41735 (7) | 0.3991 (2) | 0.68420 (11) | 0.0338 (5) | |
C8 | 0.45023 (7) | 0.2757 (2) | 0.65975 (11) | 0.0322 (4) | |
C9 | 0.43136 (7) | 0.1105 (2) | 0.65972 (12) | 0.0369 (5) | |
C10 | 0.45283 (9) | −0.0587 (3) | 0.63965 (15) | 0.0543 (6) | |
H10A | 0.4352 | −0.0958 | 0.5846 | 0.081* | |
H10B | 0.4498 | −0.1479 | 0.6789 | 0.081* | |
H10C | 0.4873 | −0.0416 | 0.6425 | 0.081* | |
C11 | 0.37116 (9) | −0.0189 (3) | 0.72999 (15) | 0.0564 (6) | |
H11A | 0.3804 | −0.1342 | 0.7151 | 0.085* | |
H11B | 0.3358 | −0.0141 | 0.7214 | 0.085* | |
H11C | 0.3875 | 0.0039 | 0.7874 | 0.085* | |
C12 | 0.50765 (7) | 0.4695 (3) | 0.62506 (11) | 0.0364 (5) | |
H12 | 0.4911 | 0.5653 | 0.6401 | 0.044* | |
C13 | 0.55036 (7) | 0.5004 (3) | 0.59315 (11) | 0.0343 (5) | |
C14 | 0.56541 (8) | 0.6741 (3) | 0.58343 (12) | 0.0433 (5) | |
H14 | 0.5484 | 0.7685 | 0.5987 | 0.052* | |
C15 | 0.60496 (8) | 0.7067 (3) | 0.55159 (13) | 0.0485 (6) | |
H15 | 0.6146 | 0.8225 | 0.5453 | 0.058* | |
C16 | 0.63050 (8) | 0.5665 (3) | 0.52878 (13) | 0.0466 (6) | |
H16 | 0.6572 | 0.5893 | 0.5070 | 0.056* | |
C17 | 0.61697 (7) | 0.3940 (3) | 0.53794 (12) | 0.0412 (5) | |
C18 | 0.57635 (7) | 0.3590 (3) | 0.56984 (12) | 0.0364 (5) | |
C19 | 0.67991 (9) | 0.2739 (4) | 0.48141 (16) | 0.0739 (8) | |
H19A | 0.6678 | 0.3392 | 0.4306 | 0.111* | |
H19B | 0.6926 | 0.1616 | 0.4696 | 0.111* | |
H19C | 0.7060 | 0.3396 | 0.5189 | 0.111* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0508 (9) | 0.0256 (8) | 0.0618 (9) | −0.0034 (6) | 0.0223 (7) | −0.0027 (7) |
O2 | 0.0545 (10) | 0.0364 (9) | 0.0698 (10) | 0.0017 (7) | 0.0312 (9) | 0.0012 (7) |
O3 | 0.0493 (10) | 0.0593 (10) | 0.0699 (10) | 0.0087 (8) | 0.0310 (8) | 0.0045 (8) |
N1 | 0.0406 (10) | 0.0256 (9) | 0.0511 (11) | −0.0028 (7) | 0.0192 (8) | −0.0023 (8) |
N2 | 0.0461 (11) | 0.0231 (9) | 0.0594 (11) | −0.0039 (7) | 0.0248 (9) | −0.0012 (8) |
N3 | 0.0357 (10) | 0.0320 (9) | 0.0393 (9) | −0.0019 (7) | 0.0120 (8) | 0.0008 (7) |
C1 | 0.0386 (12) | 0.0338 (11) | 0.0380 (11) | −0.0020 (9) | 0.0171 (10) | 0.0036 (9) |
C2 | 0.0470 (14) | 0.0487 (13) | 0.0455 (13) | −0.0101 (11) | 0.0181 (11) | −0.0073 (10) |
C3 | 0.0427 (15) | 0.0736 (17) | 0.0545 (14) | −0.0091 (12) | 0.0115 (11) | 0.0043 (13) |
C4 | 0.0429 (15) | 0.0781 (18) | 0.0667 (17) | 0.0126 (13) | 0.0222 (13) | 0.0196 (15) |
C5 | 0.0627 (17) | 0.0559 (15) | 0.0620 (16) | 0.0152 (13) | 0.0312 (14) | −0.0002 (12) |
C6 | 0.0466 (13) | 0.0444 (13) | 0.0422 (12) | 0.0026 (10) | 0.0147 (10) | −0.0042 (10) |
C7 | 0.0376 (12) | 0.0285 (11) | 0.0347 (11) | −0.0042 (9) | 0.0089 (9) | 0.0007 (9) |
C8 | 0.0353 (11) | 0.0284 (11) | 0.0336 (11) | −0.0011 (9) | 0.0106 (9) | 0.0003 (8) |
C9 | 0.0402 (12) | 0.0299 (11) | 0.0426 (12) | −0.0012 (9) | 0.0144 (10) | −0.0002 (9) |
C10 | 0.0589 (15) | 0.0312 (12) | 0.0804 (17) | 0.0013 (11) | 0.0318 (13) | −0.0059 (12) |
C11 | 0.0678 (16) | 0.0350 (13) | 0.0758 (17) | −0.0068 (11) | 0.0355 (14) | 0.0072 (12) |
C12 | 0.0374 (12) | 0.0321 (12) | 0.0395 (11) | 0.0004 (9) | 0.0100 (9) | −0.0014 (9) |
C13 | 0.0324 (11) | 0.0355 (11) | 0.0338 (11) | −0.0052 (9) | 0.0071 (9) | 0.0010 (9) |
C14 | 0.0434 (13) | 0.0387 (13) | 0.0482 (13) | −0.0041 (10) | 0.0135 (10) | −0.0019 (10) |
C15 | 0.0502 (14) | 0.0442 (13) | 0.0517 (13) | −0.0146 (11) | 0.0146 (11) | 0.0026 (11) |
C16 | 0.0385 (13) | 0.0575 (15) | 0.0462 (13) | −0.0098 (11) | 0.0154 (10) | 0.0020 (11) |
C17 | 0.0361 (12) | 0.0496 (14) | 0.0381 (12) | 0.0033 (10) | 0.0102 (10) | 0.0008 (10) |
C18 | 0.0350 (12) | 0.0349 (12) | 0.0386 (11) | −0.0021 (9) | 0.0087 (9) | 0.0022 (9) |
C19 | 0.0634 (17) | 0.091 (2) | 0.0828 (18) | 0.0222 (15) | 0.0461 (15) | 0.0181 (16) |
O1—C7 | 1.232 (2) | C7—C8 | 1.443 (3) |
O2—C18 | 1.355 (2) | C8—C9 | 1.354 (2) |
O2—H2 | 0.99 (3) | C9—C10 | 1.488 (3) |
O3—C17 | 1.375 (2) | C10—H10A | 0.9600 |
O3—C19 | 1.423 (2) | C10—H10B | 0.9600 |
N1—C7 | 1.408 (2) | C10—H10C | 0.9600 |
N1—N2 | 1.420 (2) | C11—H11A | 0.9600 |
N1—C1 | 1.426 (2) | C11—H11B | 0.9600 |
N2—C9 | 1.374 (2) | C11—H11C | 0.9600 |
N2—C11 | 1.472 (2) | C12—C13 | 1.451 (3) |
N3—C12 | 1.293 (2) | C12—H12 | 0.9300 |
N3—C8 | 1.392 (2) | C13—C14 | 1.401 (3) |
C1—C2 | 1.384 (3) | C13—C18 | 1.405 (3) |
C1—C6 | 1.385 (3) | C14—C15 | 1.372 (3) |
C2—C3 | 1.382 (3) | C14—H14 | 0.9300 |
C2—H2A | 0.9300 | C15—C16 | 1.387 (3) |
C3—C4 | 1.370 (3) | C15—H15 | 0.9300 |
C3—H3 | 0.9300 | C16—C17 | 1.377 (3) |
C4—C5 | 1.377 (3) | C16—H16 | 0.9300 |
C4—H4 | 0.9300 | C17—C18 | 1.403 (3) |
C5—C6 | 1.386 (3) | C19—H19A | 0.9600 |
C5—H5 | 0.9300 | C19—H19B | 0.9600 |
C6—H6 | 0.9300 | C19—H19C | 0.9600 |
C18—O2—H2 | 103.6 (14) | H10A—C10—H10B | 109.5 |
C17—O3—C19 | 117.20 (18) | C9—C10—H10C | 109.5 |
C7—N1—N2 | 108.98 (14) | H10A—C10—H10C | 109.5 |
C7—N1—C1 | 121.24 (15) | H10B—C10—H10C | 109.5 |
N2—N1—C1 | 118.27 (15) | N2—C11—H11A | 109.5 |
C9—N2—N1 | 106.23 (14) | N2—C11—H11B | 109.5 |
C9—N2—C11 | 122.52 (17) | H11A—C11—H11B | 109.5 |
N1—N2—C11 | 114.45 (15) | N2—C11—H11C | 109.5 |
C12—N3—C8 | 122.63 (16) | H11A—C11—H11C | 109.5 |
C2—C1—C6 | 120.3 (2) | H11B—C11—H11C | 109.5 |
C2—C1—N1 | 121.44 (18) | N3—C12—C13 | 120.94 (18) |
C6—C1—N1 | 118.20 (18) | N3—C12—H12 | 119.5 |
C3—C2—C1 | 119.6 (2) | C13—C12—H12 | 119.5 |
C3—C2—H2A | 120.2 | C14—C13—C18 | 119.13 (18) |
C1—C2—H2A | 120.2 | C14—C13—C12 | 119.72 (18) |
C4—C3—C2 | 120.5 (2) | C18—C13—C12 | 121.13 (17) |
C4—C3—H3 | 119.7 | C15—C14—C13 | 120.7 (2) |
C2—C3—H3 | 119.7 | C15—C14—H14 | 119.6 |
C3—C4—C5 | 119.8 (2) | C13—C14—H14 | 119.6 |
C3—C4—H4 | 120.1 | C14—C15—C16 | 119.9 (2) |
C5—C4—H4 | 120.1 | C14—C15—H15 | 120.1 |
C4—C5—C6 | 120.7 (2) | C16—C15—H15 | 120.1 |
C4—C5—H5 | 119.6 | C17—C16—C15 | 121.01 (19) |
C6—C5—H5 | 119.6 | C17—C16—H16 | 119.5 |
C1—C6—C5 | 119.0 (2) | C15—C16—H16 | 119.5 |
C1—C6—H6 | 120.5 | O3—C17—C16 | 125.49 (18) |
C5—C6—H6 | 120.5 | O3—C17—C18 | 114.82 (18) |
O1—C7—N1 | 122.98 (17) | C16—C17—C18 | 119.68 (19) |
O1—C7—C8 | 132.17 (18) | O2—C18—C17 | 118.33 (18) |
N1—C7—C8 | 104.81 (15) | O2—C18—C13 | 122.10 (17) |
C9—C8—N3 | 122.41 (17) | C17—C18—C13 | 119.57 (18) |
C9—C8—C7 | 108.54 (17) | O3—C19—H19A | 109.5 |
N3—C8—C7 | 128.83 (16) | O3—C19—H19B | 109.5 |
C8—C9—N2 | 110.72 (16) | H19A—C19—H19B | 109.5 |
C8—C9—C10 | 127.66 (19) | O3—C19—H19C | 109.5 |
N2—C9—C10 | 121.56 (16) | H19A—C19—H19C | 109.5 |
C9—C10—H10A | 109.5 | H19B—C19—H19C | 109.5 |
C9—C10—H10B | 109.5 | ||
C7—N1—N2—C9 | 8.8 (2) | C7—C8—C9—N2 | 3.5 (2) |
C1—N1—N2—C9 | 152.62 (16) | N3—C8—C9—C10 | 5.7 (3) |
C7—N1—N2—C11 | 147.13 (17) | C7—C8—C9—C10 | −179.19 (19) |
C1—N1—N2—C11 | −69.0 (2) | N1—N2—C9—C8 | −7.6 (2) |
C7—N1—C1—C2 | 112.1 (2) | C11—N2—C9—C8 | −141.73 (19) |
N2—N1—C1—C2 | −27.2 (2) | N1—N2—C9—C10 | 174.98 (17) |
C7—N1—C1—C6 | −64.8 (2) | C11—N2—C9—C10 | 40.8 (3) |
N2—N1—C1—C6 | 155.88 (17) | C8—N3—C12—C13 | −177.11 (16) |
C6—C1—C2—C3 | 1.4 (3) | N3—C12—C13—C14 | 178.43 (18) |
N1—C1—C2—C3 | −175.49 (18) | N3—C12—C13—C18 | 0.0 (3) |
C1—C2—C3—C4 | 0.4 (3) | C18—C13—C14—C15 | 0.0 (3) |
C2—C3—C4—C5 | −1.2 (3) | C12—C13—C14—C15 | −178.49 (18) |
C3—C4—C5—C6 | 0.3 (4) | C13—C14—C15—C16 | −0.1 (3) |
C2—C1—C6—C5 | −2.2 (3) | C14—C15—C16—C17 | −0.3 (3) |
N1—C1—C6—C5 | 174.70 (18) | C19—O3—C17—C16 | −3.9 (3) |
C4—C5—C6—C1 | 1.4 (3) | C19—O3—C17—C18 | 176.37 (18) |
N2—N1—C7—O1 | 171.60 (17) | C15—C16—C17—O3 | −178.85 (19) |
C1—N1—C7—O1 | 29.0 (3) | C15—C16—C17—C18 | 0.8 (3) |
N2—N1—C7—C8 | −6.57 (19) | O3—C17—C18—O2 | −1.5 (3) |
C1—N1—C7—C8 | −149.16 (16) | C16—C17—C18—O2 | 178.77 (18) |
C12—N3—C8—C9 | 173.05 (19) | O3—C17—C18—C13 | 178.82 (17) |
C12—N3—C8—C7 | −1.0 (3) | C16—C17—C18—C13 | −0.9 (3) |
O1—C7—C8—C9 | −176.0 (2) | C14—C13—C18—O2 | −179.16 (18) |
N1—C7—C8—C9 | 2.0 (2) | C12—C13—C18—O2 | −0.7 (3) |
O1—C7—C8—N3 | −1.3 (4) | C14—C13—C18—C17 | 0.5 (3) |
N1—C7—C8—N3 | 176.65 (17) | C12—C13—C18—C17 | 178.95 (17) |
N3—C8—C9—N2 | −171.54 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N3 | 0.99 (3) | 1.66 (3) | 2.585 (2) | 153 (2) |
C12—H12···O1 | 0.93 | 2.41 | 3.069 (2) | 128 |
C10—H10B···O1i | 0.96 | 2.40 | 3.212 (3) | 143 |
C10—H10A···O3ii | 0.96 | 2.60 | 3.468 (3) | 151 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C19H19N3O3 |
Mr | 337.37 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 294 |
a, b, c (Å) | 27.920 (6), 7.5547 (15), 16.712 (3) |
β (°) | 105.753 (4) |
V (Å3) | 3392.6 (12) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.26 × 0.24 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1999) |
Tmin, Tmax | 0.970, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9165, 3449, 2024 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.624 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.128, 1.00 |
No. of reflections | 3449 |
No. of parameters | 233 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.27 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.
O1—C7 | 1.232 (2) | N1—C1 | 1.426 (2) |
O2—C18 | 1.355 (2) | N2—C9 | 1.374 (2) |
O3—C17 | 1.375 (2) | N2—C11 | 1.472 (2) |
O3—C19 | 1.423 (2) | N3—C12 | 1.293 (2) |
N1—C7 | 1.408 (2) | N3—C8 | 1.392 (2) |
N1—N2 | 1.420 (2) | ||
C7—N1—N2 | 108.98 (14) | C9—N2—C11 | 122.52 (17) |
C7—N1—C1 | 121.24 (15) | N1—N2—C11 | 114.45 (15) |
N2—N1—C1 | 118.27 (15) | C12—N3—C8 | 122.63 (16) |
C9—N2—N1 | 106.23 (14) | N3—C12—C13 | 120.94 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N3 | 0.99 (3) | 1.66 (3) | 2.585 (2) | 153 (2) |
C12—H12···O1 | 0.93 | 2.41 | 3.069 (2) | 128 |
C10—H10B···O1i | 0.96 | 2.40 | 3.212 (3) | 143 |
C10—H10A···O3ii | 0.96 | 2.60 | 3.468 (3) | 151 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y, −z+1. |
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The synthesis of new and designed crystal structures is part of a major strand of modern chemistry. One of the aims of crystal engineering is to establish control over the preparation of crystalline solid materials, so that their architecture and properties are predictable (Parashar et al., 1988; Tynan et al., 2005). In the present study, we report the synthesis and structure of the title compound, (I) (Fig. 1 and Table 1), which will provide useful information on its physical and chemical properties.
The central system, N1/N2/C7/O1/C9/C10/N3/C8, is planar, with an r.m.s. deviation for fitted atoms of 0.038 Å, and the dihedral angle with the phenyl ring (C1–C6) is 55.17 (5)°. The o-vanillin moiety (N3/C12–C19/O2/O3) is planar, with an r.m.s. deviation for fitted atoms of 0.021 Å. The dihedral angle between the central system and the o-vanillin moiety is 7.01 (6)°. Intramolecular O—H···N and C—H···O hydrogen bonds (Table 2) stabilize the conformation of the molecule. The molecules are associated via weak C—H···O intermolecular hydrogen bonds (Table 2) to form a supramolecular structure (Fig. 2).