organic compounds
The NH unit on the exocyclic C=C double bond in the title compound, C24H21N3O, lies on the same side of the double bond as the carbonyl unit of the pyrazolone ring, and the two interact through an N—HO hydrogen bond [2.695 (2) Å].
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803029258/wk6006sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803029258/wk6006Isup2.hkl |
CCDC reference: 234837
Computing details top
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
5-Methyl-2-phenyl-4-[(Z)-(2-tolylamino)phenylmethylene]pyrazol-3(2H)-one top
Crystal data top
C24H21N3O | Z = 2 |
Mr = 367.44 | F(000) = 388 |
Triclinic, P1 | Dx = 1.217 Mg m−3 |
a = 9.792 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.832 (1) Å | Cell parameters from 848 reflections |
c = 11.556 (2) Å | θ = 2.5–26.5° |
α = 101.560 (2)° | µ = 0.08 mm−1 |
β = 99.974 (2)° | T = 298 K |
γ = 108.034 (2)° | Block, yellow |
V = 1002.9 (2) Å3 | 0.50 × 0.35 × 0.20 mm |
Data collection top
Bruker SMART area-detector diffractometer | 2832 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.012 |
Graphite monochromator | θmax = 27.1°, θmin = 1.9° |
φ and ω scans | h = −12→12 |
8614 measured reflections | k = −12→12 |
4346 independent reflections | l = −14→14 |
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)] = 0.043 | Hydrogen site location: mixed |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0626P)2 + 0.1426P] where P = (Fo2 + 2Fc2)/3 |
4346 reflections | (Δ/σ)max < 0.001 |
259 parameters | Δρmax = 0.15 e Å−3 |
1 restraint | Δρmin = −0.14 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.6974 (1) | 0.6541 (1) | 0.4937 (1) | 0.0671 (3) | |
N1 | 0.8513 (1) | 0.8087 (1) | 0.6838 (1) | 0.0587 (3) | |
N2 | 1.0030 (1) | 0.8909 (2) | 0.7332 (1) | 0.0660 (4) | |
N3 | 0.8634 (2) | 0.6158 (2) | 0.3355 (1) | 0.0633 (4) | |
C1 | 0.7521 (2) | 0.8179 (2) | 0.7585 (1) | 0.0581 (4) | |
C2 | 0.8022 (2) | 0.9241 (2) | 0.8695 (2) | 0.0707 (5) | |
C3 | 0.7046 (2) | 0.9353 (2) | 0.9410 (2) | 0.0852 (6) | |
C4 | 0.5601 (2) | 0.8440 (3) | 0.9044 (2) | 0.0868 (6) | |
C5 | 0.5114 (2) | 0.7390 (2) | 0.7945 (2) | 0.0884 (6) | |
C6 | 0.6061 (2) | 0.7234 (2) | 0.7212 (2) | 0.0778 (5) | |
C7 | 0.8215 (2) | 0.7327 (2) | 0.5632 (1) | 0.0535 (4) | |
C8 | 0.9650 (2) | 0.7643 (2) | 0.5370 (1) | 0.0527 (4) | |
C9 | 1.0685 (2) | 0.8640 (2) | 0.6471 (2) | 0.0603 (4) | |
C10 | 1.2334 (2) | 0.9366 (2) | 0.6729 (2) | 0.0914 (6) | |
C11 | 0.9832 (2) | 0.7019 (2) | 0.4244 (1) | 0.0506 (3) | |
C12 | 1.1329 (2) | 0.7298 (2) | 0.4011 (1) | 0.0509 (3) | |
C13 | 1.1910 (2) | 0.8400 (2) | 0.3475 (2) | 0.0655 (4) | |
C14 | 1.3332 (2) | 0.8700 (2) | 0.3322 (2) | 0.0812 (5) | |
C15 | 1.4147 (2) | 0.7884 (2) | 0.3678 (2) | 0.0819 (6) | |
C16 | 1.3573 (2) | 0.6774 (2) | 0.4196 (2) | 0.0795 (5) | |
C17 | 1.2171 (2) | 0.6493 (2) | 0.4376 (2) | 0.0676 (4) | |
C18 | 0.8563 (2) | 0.5327 (2) | 0.2168 (1) | 0.0604 (4) | |
C19 | 0.9211 (2) | 0.4264 (2) | 0.2043 (2) | 0.0755 (5) | |
C20 | 0.9094 (3) | 0.3416 (3) | 0.0913 (2) | 0.1009 (7) | |
C21 | 0.8326 (3) | 0.3614 (3) | −0.0081 (2) | 0.1103 (8) | |
C22 | 0.7658 (3) | 0.4644 (3) | 0.0019 (2) | 0.1074 (8) | |
C23 | 0.7766 (2) | 0.5548 (2) | 0.1169 (2) | 0.0829 (5) | |
C24 | 0.7038 (4) | 0.6685 (4) | 0.1313 (3) | 0.147 (1) | |
H3n | 0.781 (1) | 0.610 (2) | 0.357 (2) | 0.087 (6)* | |
H2 | 0.9009 | 0.9876 | 0.8961 | 0.085* | |
H3 | 0.7387 | 1.0070 | 1.0157 | 0.102* | |
H4 | 0.4955 | 0.8527 | 0.9532 | 0.104* | |
H5 | 0.4123 | 0.6766 | 0.7684 | 0.106* | |
H6 | 0.5716 | 0.6498 | 0.6475 | 0.093* | |
H10a | 1.2569 | 0.9962 | 0.6176 | 0.137* | |
H10b | 1.2774 | 0.8617 | 0.6622 | 0.137* | |
H10c | 1.2718 | 0.9986 | 0.7554 | 0.137* | |
H13 | 1.1348 | 0.8942 | 0.3217 | 0.079* | |
H14 | 1.3734 | 0.9459 | 0.2976 | 0.097* | |
H15 | 1.5100 | 0.8085 | 0.3566 | 0.098* | |
H16 | 1.4127 | 0.6212 | 0.4426 | 0.095* | |
H17 | 1.1788 | 0.5754 | 0.4748 | 0.081* | |
H19 | 0.9732 | 0.4122 | 0.2734 | 0.091* | |
H20 | 0.9543 | 0.2707 | 0.0832 | 0.121* | |
H21 | 0.8248 | 0.3038 | −0.0850 | 0.132* | |
H22 | 0.7122 | 0.4752 | −0.0682 | 0.129* | |
H24a | 0.6284 | 0.6408 | 0.1743 | 0.220* | |
H24b | 0.6595 | 0.6738 | 0.0522 | 0.220* | |
H24c | 0.7768 | 0.7637 | 0.1766 | 0.220* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0431 (6) | 0.0806 (8) | 0.0691 (7) | 0.0190 (5) | 0.0118 (5) | 0.0092 (6) |
N1 | 0.0472 (7) | 0.0632 (8) | 0.0622 (8) | 0.0178 (6) | 0.0167 (6) | 0.0099 (6) |
N2 | 0.0506 (7) | 0.0701 (9) | 0.0672 (8) | 0.0150 (6) | 0.0149 (6) | 0.0067 (7) |
N3 | 0.0462 (7) | 0.0766 (9) | 0.0609 (8) | 0.0192 (7) | 0.0137 (6) | 0.0090 (7) |
C1 | 0.058 (1) | 0.062 (1) | 0.064 (1) | 0.026 (1) | 0.023 (1) | 0.022 (1) |
C2 | 0.073 (1) | 0.076 (1) | 0.065 (1) | 0.026 (1) | 0.025 (1) | 0.018 (1) |
C3 | 0.100 (2) | 0.091 (1) | 0.074 (1) | 0.037 (1) | 0.042 (1) | 0.020 (1) |
C4 | 0.094 (2) | 0.100 (2) | 0.093 (2) | 0.045 (1) | 0.056 (1) | 0.037 (1) |
C5 | 0.067 (1) | 0.099 (2) | 0.103 (2) | 0.023 (1) | 0.041 (1) | 0.028 (1) |
C6 | 0.063 (1) | 0.083 (1) | 0.083 (1) | 0.019 (1) | 0.031 (1) | 0.013 (1) |
C7 | 0.047 (1) | 0.054 (1) | 0.061 (1) | 0.019 (1) | 0.013 (1) | 0.014 (1) |
C8 | 0.045 (1) | 0.052 (1) | 0.060 (1) | 0.018 (1) | 0.015 (1) | 0.014 (1) |
C9 | 0.047 (1) | 0.059 (1) | 0.068 (1) | 0.014 (1) | 0.015 (1) | 0.010 (1) |
C10 | 0.053 (1) | 0.099 (1) | 0.088 (1) | 0.003 (1) | 0.017 (1) | −0.010 (1) |
C11 | 0.047 (1) | 0.048 (1) | 0.060 (1) | 0.019 (1) | 0.014 (1) | 0.018 (1) |
C12 | 0.047 (1) | 0.050 (1) | 0.056 (1) | 0.016 (1) | 0.015 (1) | 0.013 (1) |
C13 | 0.061 (1) | 0.066 (1) | 0.075 (1) | 0.021 (1) | 0.021 (1) | 0.030 (1) |
C14 | 0.066 (1) | 0.085 (1) | 0.094 (1) | 0.013 (1) | 0.034 (1) | 0.039 (1) |
C15 | 0.050 (1) | 0.093 (1) | 0.096 (1) | 0.016 (1) | 0.028 (1) | 0.018 (1) |
C16 | 0.055 (1) | 0.081 (1) | 0.109 (2) | 0.033 (1) | 0.022 (1) | 0.025 (1) |
C17 | 0.055 (1) | 0.066 (1) | 0.092 (1) | 0.025 (1) | 0.023 (1) | 0.033 (1) |
C18 | 0.052 (1) | 0.062 (1) | 0.058 (1) | 0.010 (1) | 0.015 (1) | 0.013 (1) |
C19 | 0.074 (1) | 0.071 (1) | 0.077 (1) | 0.024 (1) | 0.020 (1) | 0.011 (1) |
C20 | 0.099 (2) | 0.088 (2) | 0.098 (2) | 0.025 (1) | 0.031 (1) | −0.006 (1) |
C21 | 0.110 (2) | 0.114 (2) | 0.076 (2) | 0.014 (2) | 0.031 (1) | −0.004 (1) |
C22 | 0.106 (2) | 0.123 (2) | 0.066 (1) | 0.014 (2) | 0.002 (1) | 0.026 (1) |
C23 | 0.079 (1) | 0.088 (1) | 0.072 (1) | 0.020 (1) | 0.007 (1) | 0.025 (1) |
C24 | 0.167 (3) | 0.151 (3) | 0.130 (2) | 0.091 (2) | −0.012 (2) | 0.041 (2) |
Geometric parameters (Å, º) top
O1—C7 | 1.245 (2) | C19—C20 | 1.366 (3) |
N1—C7 | 1.376 (2) | C20—C21 | 1.343 (4) |
N1—N2 | 1.402 (2) | C21—C22 | 1.362 (4) |
N1—C1 | 1.418 (2) | C22—C23 | 1.410 (3) |
N2—C9 | 1.300 (2) | C23—C24 | 1.498 (3) |
N3—C11 | 1.329 (2) | N3—H3n | 0.87 (1) |
N3—C18 | 1.427 (2) | C2—H2 | 0.93 |
C1—C6 | 1.377 (2) | C3—H3 | 0.93 |
C1—C2 | 1.380 (2) | C4—H4 | 0.93 |
C2—C3 | 1.381 (2) | C5—H5 | 0.93 |
C3—C4 | 1.357 (3) | C6—H6 | 0.93 |
C4—C5 | 1.366 (3) | C10—H10a | 0.96 |
C5—C6 | 1.382 (3) | C10—H10b | 0.96 |
C7—C8 | 1.441 (2) | C10—H10c | 0.96 |
C8—C9 | 1.430 (2) | C13—H13 | 0.93 |
C8—C11 | 1.390 (2) | C14—H14 | 0.93 |
C9—C10 | 1.497 (2) | C15—H15 | 0.93 |
C11—C12 | 1.488 (2) | C16—H16 | 0.93 |
C12—C13 | 1.375 (2) | C17—H17 | 0.93 |
C12—C17 | 1.379 (2) | C19—H19 | 0.93 |
C13—C14 | 1.381 (2) | C20—H20 | 0.93 |
C14—C15 | 1.366 (3) | C21—H21 | 0.93 |
C15—C16 | 1.365 (3) | C22—H22 | 0.93 |
C16—C17 | 1.375 (2) | C24—H24a | 0.96 |
C18—C19 | 1.377 (2) | C24—H24b | 0.96 |
C18—C23 | 1.373 (2) | C24—H24c | 0.96 |
N2—N1—C7 | 111.9 (1) | C11—N3—H3n | 113 (1) |
N2—N1—C1 | 118.6 (1) | C18—N3—H3n | 119 (1) |
C1—N1—C7 | 129.5 (1) | C3—C2—H2 | 120.3 |
N1—N2—C9 | 106.5 (1) | C1—C2—H2 | 120.3 |
C11—N3—C18 | 128.3 (1) | C4—C3—H3 | 119.3 |
N1—C1—C2 | 119.5 (2) | C2—C3—H3 | 119.3 |
N1—C1—C6 | 120.9 (2) | C3—C4—H4 | 120.6 |
C2—C1—C6 | 119.6 (2) | C5—C4—H4 | 120.6 |
C3—C2—C1 | 119.5 (2) | C4—C5—H5 | 119.3 |
C4—C3—C2 | 121.4 (2) | C6—C5—H5 | 119.3 |
C3—C4—C5 | 118.8 (2) | C1—C6—H6 | 120.4 |
C4—C5—C6 | 121.5 (2) | C5—C6—H6 | 120.4 |
C1—C6—C5 | 119.3 (2) | C9—C10—H10a | 109.5 |
O1—C7—N1 | 127.0 (1) | C9—C10—H10b | 109.5 |
O1—C7—C8 | 128.5 (1) | H10a—C10—H10b | 109.5 |
N1—C7—C8 | 104.5 (1) | C9—C10—H10c | 109.5 |
C7—C8—C9 | 105.3 (1) | H10a—C10—H10c | 109.5 |
C7—C8—C11 | 122.4 (1) | H10b—C10—H10c | 109.5 |
C9—C8—C11 | 132.3 (1) | C12—C13—H13 | 120.1 |
N2—C9—C8 | 111.8 (1) | C14—C13—H13 | 120.1 |
N2—C9—C10 | 119.0 (2) | C15—C14—H14 | 119.9 |
C8—C9—C10 | 129.2 (2) | C13—C14—H14 | 119.9 |
N3—C11—C8 | 118.9 (1) | C16—C15—H15 | 119.8 |
N3—C11—C12 | 119.5 (1) | C14—C15—H15 | 119.8 |
C8—C11—C12 | 121.6 (1) | C15—C16—H16 | 120.2 |
C13—C12—C17 | 119.4 (1) | C17—C16—H16 | 120.2 |
C11—C12—C13 | 120.3 (1) | C16—C17—H17 | 119.7 |
C11—C12—C17 | 120.2 (1) | C12—C17—H17 | 119.7 |
C12—C13—C14 | 119.8 (2) | C20—C19—H19 | 119.7 |
C13—C14—C15 | 120.2 (2) | C18—C19—H19 | 119.7 |
C14—C15—C16 | 120.5 (2) | C21—C20—H20 | 120.3 |
C15—C16—C17 | 119.6 (2) | C19—C20—H20 | 120.3 |
C12—C17—C17 | 120.5 (2) | C20—C21—H21 | 119.4 |
C19—C18—C23 | 121.2 (2) | C22—C21—H21 | 119.4 |
N3—C18—C23 | 118.6 (2) | C21—C22—H22 | 119.5 |
N3—C18—C19 | 120.1 (2) | C23—C22—H22 | 119.5 |
C18—C19—C20 | 120.6 (2) | C23—C24—H24a | 109.5 |
C19—C20—C21 | 119.5 (2) | C23—C24—H24b | 109.5 |
C20—C21—C22 | 121.1 (2) | H24a—C24—H24b | 109.5 |
C21—C22—C23 | 121.0 (2) | C23—C24—H24c | 109.5 |
C18—C23—C22 | 116.6 (2) | H24a—C24—H24c | 109.5 |
C18—C23—C24 | 120.9 (2) | H24b—C24—H24c | 109.5 |
C22—C23—C24 | 122.4 (2) | ||
C7—N1—N2—C9 | −1.9 (2) | C9—C8—C11—N3 | −177.3 (2) |
C1—N1—N2—C9 | −179.7 (1) | C7—C8—C11—N3 | 3.5 (2) |
C7—N1—C1—C6 | 12.4 (3) | C9—C8—C11—C12 | 2.5 (2) |
N2—N1—C1—C6 | −170.2 (2) | C7—C8—C11—C12 | −176.8 (1) |
C7—N1—C1—C2 | −166.9 (2) | N3—C11—C12—C13 | 84.0 (2) |
N2—N1—C1—C2 | 10.5 (2) | C8—C11—C12—C13 | −95.7 (2) |
C6—C1—C2—C3 | −0.8 (3) | N3—C11—C12—C17 | −98.6 (2) |
N1—C1—C2—C3 | 178.4 (2) | C8—C11—C12—C17 | 81.7 (2) |
C1—C2—C3—C4 | 0.0 (3) | C17—C12—C13—C14 | −0.7 (3) |
C2—C3—C4—C5 | 0.1 (3) | C11—C12—C13—C14 | 176.6 (2) |
C3—C4—C5—C6 | 0.6 (3) | C12—C13—C14—C15 | 1.4 (3) |
C2—C1—C6—C5 | 1.5 (3) | C13—C14—C15—C16 | −0.5 (3) |
N1—C1—C6—C5 | −177.8 (2) | C14—C15—C16—C17 | −0.9 (3) |
C4—C5—C6—C1 | −1.4 (3) | C15—C16—C17—C12 | 1.6 (3) |
N2—N1—C7—O1 | −177.6 (1) | C13—C12—C17—C16 | −0.7 (3) |
C1—N1—C7—O1 | −0.2 (3) | C11—C12—C17—C16 | −178.1 (2) |
N2—N1—C7—C8 | 2.6 (2) | C11—N3—C18—C23 | −125.3 (2) |
C1—N1—C7—C8 | −179.9 (1) | C11—N3—C18—C19 | 58.6 (2) |
O1—C7—C8—C11 | −2.6 (2) | C23—C18—C19—C20 | 1.1 (3) |
N1—C7—C8—C11 | 177.1 (1) | N3—C18—C19—C20 | 177.1 (2) |
O1—C7—C8—C9 | 178.0 (2) | C18—C19—C20—C21 | −0.7 (3) |
N1—C7—C8—C9 | −2.3 (2) | C19—C20—C21—C22 | −0.1 (4) |
N1—N2—C9—C8 | 0.3 (2) | C20—C21—C22—C23 | 0.7 (4) |
N1—N2—C9—C10 | −179.8 (2) | C19—C18—C23—C22 | −0.5 (3) |
C11—C8—C9—N2 | −178.1 (2) | N3—C18—C23—C22 | −176.6 (2) |
C7—C8—C9—N2 | 1.3 (2) | C19—C18—C23—C24 | 178.7 (2) |
C11—C8—C9—C10 | 2.0 (3) | N3—C18—C23—C24 | 2.7 (3) |
C7—C8—C9—C10 | −178.6 (2) | C21—C22—C23—C18 | −0.4 (3) |
C18—N3—C11—C8 | −175.1 (2) | C21—C22—C23—C24 | −179.6 (3) |
C18—N3—C11—C12 | 5.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3n···O1 | 0.87 (1) | 1.94 (1) | 2.695 (2) | 144 (2) |