organic compounds
The crystal structure of the title compound, C24H21N3O2, features a central pyrazole ring; the NH unit interacts with the C=O unit through an intramolecular hydrogen bond [NO = 2.714 (1) Å].
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680402728X/bt6554sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680402728X/bt6554Isup2.hkl |
CCDC reference: 259099
Computing details top
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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.
4-[(Z)-(4-Methoxyanilino)phenylmethylene]-5-methyl-2-phenyl-2H-pyrazol-3(4H)-one top
Crystal data top
C24H21N3O2 | Z = 2 |
Mr = 383.44 | F(000) = 404 |
Triclinic, P1 | Dx = 1.261 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.8262 (9) Å | Cell parameters from 904 reflections |
b = 10.951 (1) Å | θ = 2.0–27.1° |
c = 14.761 (1) Å | µ = 0.08 mm−1 |
α = 97.259 (2)° | T = 298 K |
β = 103.386 (2)° | Block, yellow |
γ = 106.018 (2)° | 0.50 × 0.50 × 0.20 mm |
V = 1010.2 (2) Å3 |
Data collection top
Bruker SMART area-detector diffractometer | 3303 reflections with I > 2σ(I) |
Radiation source: medium-focus sealed tube | Rint = 0.013 |
Graphite monochromator | θmax = 27.1°, θmin = 2.0° |
φ and ω scans | h = −8→8 |
8643 measured reflections | k = −13→13 |
4350 independent reflections | l = −18→18 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0692P)2 + 0.1202P] where P = (Fo2 + 2Fc2)/3 |
4350 reflections | (Δ/σ)max = 0.001 |
268 parameters | Δρmax = 0.15 e Å−3 |
1 restraint | Δρmin = −0.19 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.5354 (2) | 0.6041 (1) | 0.7503 (1) | 0.0563 (3) | |
O2 | 1.1065 (2) | 0.2880 (1) | 0.4206 (1) | 0.0703 (3) | |
N1 | 0.3569 (2) | 0.5293 (1) | 0.8597 (1) | 0.0502 (3) | |
N2 | 0.2916 (2) | 0.4135 (1) | 0.8910 (1) | 0.0533 (3) | |
N3 | 0.6537 (2) | 0.4113 (1) | 0.6670 (1) | 0.0518 (3) | |
C1 | 0.2788 (2) | 0.6313 (1) | 0.8864 (1) | 0.0521 (3) | |
C2 | 0.3840 (3) | 0.7573 (1) | 0.8827 (1) | 0.0628 (4) | |
C3 | 0.3027 (4) | 0.8552 (2) | 0.9082 (1) | 0.0786 (5) | |
C4 | 0.1207 (4) | 0.8285 (2) | 0.9373 (1) | 0.0857 (6) | |
C5 | 0.0179 (3) | 0.7033 (2) | 0.9414 (1) | 0.0789 (5) | |
C6 | 0.0961 (3) | 0.6041 (2) | 0.9159 (1) | 0.0637 (4) | |
C7 | 0.4706 (2) | 0.5197 (1) | 0.7949 (1) | 0.0460 (3) | |
C8 | 0.4872 (2) | 0.3905 (1) | 0.7890 (1) | 0.0449 (3) | |
C9 | 0.3697 (2) | 0.3331 (1) | 0.8502 (1) | 0.0479 (3) | |
C10 | 0.3232 (3) | 0.1993 (1) | 0.8697 (1) | 0.0628 (4) | |
C11 | 0.5816 (2) | 0.3399 (1) | 0.7259 (1) | 0.0449 (3) | |
C12 | 0.5937 (2) | 0.2059 (1) | 0.7174 (1) | 0.0481 (3) | |
C13 | 0.7182 (2) | 0.1699 (2) | 0.7903 (1) | 0.0647 (4) | |
C14 | 0.7220 (3) | 0.0435 (2) | 0.7806 (2) | 0.0810 (5) | |
C15 | 0.6023 (3) | −0.0462 (2) | 0.6993 (2) | 0.0841 (5) | |
C16 | 0.4808 (3) | −0.0109 (2) | 0.6263 (1) | 0.0790 (5) | |
C17 | 0.4764 (2) | 0.1151 (1) | 0.6344 (1) | 0.0612 (4) | |
C18 | 0.7670 (2) | 0.3783 (1) | 0.6026 (1) | 0.0469 (3) | |
C19 | 0.9546 (2) | 0.3520 (1) | 0.6354 (1) | 0.0558 (3) | |
C20 | 1.0618 (2) | 0.3212 (2) | 0.5723 (1) | 0.0593 (4) | |
C21 | 0.9851 (2) | 0.3174 (1) | 0.4765 (1) | 0.0502 (3) | |
C22 | 0.7992 (2) | 0.3455 (1) | 0.4434 (1) | 0.0489 (3) | |
C23 | 0.6906 (2) | 0.3751 (1) | 0.5071 (1) | 0.0484 (3) | |
C24 | 1.0161 (3) | 0.2602 (2) | 0.3208 (1) | 0.0798 (5) | |
H3n | 0.635 (3) | 0.487 (1) | 0.675 (1) | 0.069 (5)* | |
H2 | 0.5075 | 0.7761 | 0.8633 | 0.075* | |
H3 | 0.3721 | 0.9401 | 0.9056 | 0.094* | |
H4 | 0.0676 | 0.8949 | 0.9542 | 0.103* | |
H5 | −0.1048 | 0.6850 | 0.9613 | 0.095* | |
H6 | 0.0261 | 0.5194 | 0.9187 | 0.076* | |
H10a | 0.2271 | 0.1879 | 0.9085 | 0.094* | |
H10b | 0.4528 | 0.1867 | 0.9024 | 0.094* | |
H10c | 0.2597 | 0.1372 | 0.8106 | 0.094* | |
H13 | 0.7992 | 0.2304 | 0.8457 | 0.078* | |
H14 | 0.8062 | 0.0191 | 0.8296 | 0.097* | |
H15 | 0.6038 | −0.1314 | 0.6938 | 0.101* | |
H16 | 0.4010 | −0.0719 | 0.5710 | 0.095* | |
H17 | 0.3950 | 0.1393 | 0.5843 | 0.073* | |
H19 | 1.0080 | 0.3550 | 0.6998 | 0.067* | |
H20 | 1.1874 | 0.3028 | 0.5944 | 0.071* | |
H22 | 0.7477 | 0.3446 | 0.3791 | 0.059* | |
H23 | 0.5644 | 0.3930 | 0.4851 | 0.058* | |
H24a | 0.8893 | 0.1869 | 0.3035 | 0.120* | |
H24b | 1.1159 | 0.2408 | 0.2896 | 0.120* | |
H24c | 0.9820 | 0.3341 | 0.3016 | 0.120* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.069 (1) | 0.047 (1) | 0.063 (1) | 0.022 (1) | 0.028 (1) | 0.020 (1) |
O2 | 0.061 (1) | 0.092 (1) | 0.063 (1) | 0.033 (1) | 0.021 (1) | 0.004 (1) |
N1 | 0.064 (1) | 0.041 (1) | 0.051 (1) | 0.019 (1) | 0.021 (1) | 0.011 (1) |
N2 | 0.067 (1) | 0.046 (1) | 0.052 (1) | 0.020 (1) | 0.023 (1) | 0.015 (1) |
N3 | 0.061 (1) | 0.045 (1) | 0.059 (1) | 0.023 (1) | 0.025 (1) | 0.015 (1) |
C1 | 0.068 (1) | 0.049 (1) | 0.042 (1) | 0.026 (1) | 0.014 (1) | 0.005 (1) |
C2 | 0.084 (1) | 0.048 (1) | 0.057 (1) | 0.025 (1) | 0.018 (1) | 0.008 (1) |
C3 | 0.121 (2) | 0.054 (1) | 0.064 (1) | 0.040 (1) | 0.019 (1) | 0.008 (1) |
C4 | 0.130 (2) | 0.082 (1) | 0.064 (1) | 0.069 (1) | 0.026 (1) | 0.006 (1) |
C5 | 0.099 (1) | 0.093 (1) | 0.064 (1) | 0.054 (1) | 0.032 (1) | 0.010 (1) |
C6 | 0.078 (1) | 0.063 (1) | 0.057 (1) | 0.029 (1) | 0.026 (1) | 0.009 (1) |
C7 | 0.050 (1) | 0.042 (1) | 0.045 (1) | 0.015 (1) | 0.010 (1) | 0.008 (1) |
C8 | 0.048 (1) | 0.042 (1) | 0.044 (1) | 0.016 (1) | 0.010 (1) | 0.009 (1) |
C9 | 0.054 (1) | 0.044 (1) | 0.046 (1) | 0.016 (1) | 0.012 (1) | 0.010 (1) |
C10 | 0.079 (1) | 0.050 (1) | 0.070 (1) | 0.023 (1) | 0.032 (1) | 0.022 (1) |
C11 | 0.042 (1) | 0.044 (1) | 0.046 (1) | 0.014 (1) | 0.007 (1) | 0.008 (1) |
C12 | 0.047 (1) | 0.043 (1) | 0.057 (1) | 0.015 (1) | 0.016 (1) | 0.009 (1) |
C13 | 0.061 (1) | 0.054 (1) | 0.074 (1) | 0.022 (1) | 0.005 (1) | 0.015 (1) |
C14 | 0.071 (1) | 0.065 (1) | 0.115 (2) | 0.034 (1) | 0.016 (1) | 0.035 (1) |
C15 | 0.085 (1) | 0.045 (1) | 0.128 (2) | 0.027 (1) | 0.033 (1) | 0.016 (1) |
C16 | 0.091 (1) | 0.048 (1) | 0.090 (1) | 0.016 (1) | 0.025 (1) | 0.000 (1) |
C17 | 0.066 (1) | 0.048 (1) | 0.064 (1) | 0.015 (1) | 0.014 (1) | 0.006 (1) |
C18 | 0.048 (1) | 0.042 (1) | 0.053 (1) | 0.015 (1) | 0.017 (1) | 0.010 (1) |
C19 | 0.052 (1) | 0.067 (1) | 0.047 (1) | 0.021 (1) | 0.008 (1) | 0.011 (1) |
C20 | 0.045 (1) | 0.074 (1) | 0.060 (1) | 0.027 (1) | 0.009 (1) | 0.012 (1) |
C21 | 0.046 (1) | 0.049 (1) | 0.054 (1) | 0.014 (1) | 0.015 (1) | 0.005 (1) |
C22 | 0.050 (1) | 0.046 (1) | 0.047 (1) | 0.014 (1) | 0.010 (1) | 0.009 (1) |
C23 | 0.046 (1) | 0.045 (1) | 0.057 (1) | 0.019 (1) | 0.012 (1) | 0.014 (1) |
C24 | 0.082 (1) | 0.099 (1) | 0.061 (1) | 0.028 (1) | 0.031 (1) | 0.006 (1) |
Geometric parameters (Å, º) top
O1—C7 | 1.244 (2) | C18—C19 | 1.382 (2) |
O2—C21 | 1.366 (2) | C19—C20 | 1.374 (2) |
O2—C24 | 1.416 (2) | C20—C21 | 1.381 (2) |
N1—N2 | 1.397 (2) | C21—C22 | 1.382 (2) |
N1—C7 | 1.376 (2) | C22—C23 | 1.385 (2) |
N1—C1 | 1.414 (2) | N3—H3n | 0.87 (1) |
N2—C9 | 1.303 (2) | C2—H2 | 0.9300 |
N3—C11 | 1.329 (2) | C3—H3 | 0.9300 |
N3—C18 | 1.428 (2) | C4—H4 | 0.9300 |
C1—C6 | 1.383 (2) | C5—H5 | 0.9300 |
C1—C2 | 1.383 (2) | C6—H6 | 0.9300 |
C2—C3 | 1.386 (2) | C10—H10a | 0.9600 |
C3—C4 | 1.376 (3) | C10—H10b | 0.9600 |
C4—C5 | 1.373 (3) | C10—H10c | 0.9600 |
C5—C6 | 1.384 (2) | C13—H13 | 0.9300 |
C7—C8 | 1.444 (2) | C14—H14 | 0.9300 |
C8—C11 | 1.391 (2) | C15—H15 | 0.9300 |
C8—C9 | 1.433 (2) | C16—H16 | 0.9300 |
C9—C10 | 1.490 (2) | C17—H17 | 0.9300 |
C11—C12 | 1.484 (2) | C19—H19 | 0.9300 |
C12—C13 | 1.381 (2) | C20—H20 | 0.9300 |
C12—C17 | 1.389 (2) | C22—H22 | 0.9300 |
C13—C14 | 1.382 (2) | C23—H23 | 0.9300 |
C14—C15 | 1.370 (3) | C24—H24a | 0.9600 |
C15—C16 | 1.367 (3) | C24—H24b | 0.9600 |
C16—C17 | 1.379 (2) | C24—H24c | 0.9600 |
C18—C23 | 1.378 (2) | ||
C21—O2—C24 | 117.4 (1) | C18—C23—C22 | 120.8 (1) |
N2—N1—C1 | 118.7 (1) | C11—N3—H3n | 113 (1) |
N2—N1—C7 | 112.2 (1) | C18—N3—H3n | 121 (1) |
C1—N1—C7 | 128.5 (1) | C1—C2—H2 | 120.5 |
C9—N2—N1 | 106.4 (1) | C3—C2—H2 | 120.5 |
C11—N3—C18 | 126.4 (1) | C4—C3—H3 | 119.5 |
C6—C1—C2 | 120.2 (1) | C2—C3—H3 | 119.5 |
C6—C1—N1 | 119.6 (1) | C5—C4—H4 | 120.2 |
C2—C1—N1 | 120.2 (1) | C3—C4—H4 | 120.2 |
C1—C2—C3 | 119.0 (2) | C4—C5—H5 | 119.8 |
C4—C3—C2 | 120.9 (2) | C6—C5—H5 | 119.8 |
C5—C4—C3 | 119.7 (2) | C1—C6—H6 | 120.1 |
C4—C5—C6 | 120.3 (2) | C5—C6—H6 | 120.1 |
C1—C6—C5 | 119.8 (2) | C9—C10—H10a | 109.5 |
O1—C7—N1 | 126.2 (1) | C9—C10—H10b | 109.5 |
N1—C7—C8 | 104.4 (1) | H10a—C10—H10b | 109.5 |
O1—C7—C8 | 129.3 (1) | C9—C10—H10c | 109.5 |
C7—C8—C9 | 105.2 (1) | H10a—C10—H10c | 109.5 |
C7—C8—C11 | 122.2 (1) | H10b—C10—H10c | 109.5 |
C9—C8—C11 | 132.2 (1) | C14—C13—H13 | 120.2 |
N2—C9—C8 | 111.7 (1) | C12—C13—H13 | 120.2 |
N2—C9—C10 | 118.5 (1) | C15—C14—H14 | 119.8 |
C8—C9—C10 | 129.8 (1) | C13—C14—H14 | 119.8 |
N3—C11—C8 | 119.1 (1) | C14—C15—H15 | 119.8 |
N3—C11—C12 | 118.3 (1) | C16—C15—H15 | 119.8 |
C8—C11—C12 | 122.6 (1) | C15—C16—H16 | 119.9 |
C13—C12—C17 | 119.6 (1) | C17—C16—H16 | 119.9 |
C13—C12—C11 | 121.3 (1) | C16—C17—H17 | 120.0 |
C17—C12—C11 | 119.1 (1) | C12—C17—H17 | 120.0 |
C14—C13—C12 | 119.7 (2) | C20—C19—H19 | 120.1 |
C15—C14—C13 | 120.4 (2) | C18—C19—H19 | 120.1 |
C14—C15—C16 | 120.3 (2) | C19—C20—H20 | 119.6 |
C15—C16—C17 | 120.1 (2) | C21—C20—H20 | 119.6 |
C16—C17—C12 | 119.9 (2) | C21—C22—H22 | 120.4 |
C23—C18—C19 | 119.7 (1) | C23—C22—H22 | 120.4 |
C23—C18—N3 | 119.7 (1) | C18—C23—H23 | 119.6 |
C19—C18—N3 | 120.7 (1) | C22—C23—H23 | 119.6 |
C20—C19—C18 | 119.8 (1) | O2—C24—H24a | 109.5 |
C19—C20—C21 | 120.7 (1) | O2—C24—H24b | 109.5 |
O2—C21—C20 | 115.7 (1) | H24a—C24—H24b | 109.5 |
O2—C21—C22 | 124.4 (1) | O2—C24—H24c | 109.5 |
C20—C21—C22 | 119.8 (1) | H24a—C24—H24c | 109.5 |
C21—C22—C23 | 119.2 (1) | H24b—C24—H24c | 109.5 |
C7—N1—N2—C9 | 2.6 (2) | C9—C8—C11—N3 | 169.8 (1) |
C1—N1—N2—C9 | 174.5 (1) | C7—C8—C11—N3 | −1.9 (2) |
C7—N1—C1—C6 | 150.4 (1) | C9—C8—C11—C12 | −6.5 (2) |
N2—N1—C1—C6 | −19.9 (2) | C7—C8—C11—C12 | −178.2 (1) |
C7—N1—C1—C2 | −29.4 (2) | N3—C11—C12—C13 | 116.0 (2) |
N2—N1—C1—C2 | 160.3 (1) | C8—C11—C12—C13 | −67.8 (2) |
C6—C1—C2—C3 | −0.5 (2) | N3—C11—C12—C17 | −64.3 (2) |
N1—C1—C2—C3 | 179.3 (1) | C8—C11—C12—C17 | 112.0 (2) |
C1—C2—C3—C4 | 0.3 (2) | C17—C12—C13—C14 | −1.1 (2) |
C2—C3—C4—C5 | 0.1 (3) | C11—C12—C13—C14 | 178.6 (1) |
C3—C4—C5—C6 | −0.3 (3) | C12—C13—C14—C15 | −0.3 (3) |
C2—C1—C6—C5 | 0.3 (2) | C13—C14—C15—C16 | 1.1 (3) |
N1—C1—C6—C5 | −179.5 (1) | C14—C15—C16—C17 | −0.6 (3) |
C4—C5—C6—C1 | 0.0 (2) | C15—C16—C17—C12 | −0.8 (3) |
N2—N1—C7—O1 | 174.6 (1) | C13—C12—C17—C16 | 1.6 (2) |
C1—N1—C7—O1 | 3.7 (2) | C11—C12—C17—C16 | −178.1 (1) |
N2—N1—C7—C8 | −3.1 (1) | C11—N3—C18—C23 | 123.8 (2) |
C1—N1—C7—C8 | −174.0 (1) | C11—N3—C18—C19 | −57.4 (2) |
O1—C7—C8—C11 | −1.6 (2) | C23—C18—C19—C20 | −0.8 (2) |
N1—C7—C8—C11 | 176.1 (1) | N3—C18—C19—C20 | −179.6 (1) |
O1—C7—C8—C9 | −175.2 (1) | C18—C19—C20—C21 | 0.5 (2) |
N1—C7—C8—C9 | 2.4 (1) | C24—O2—C21—C20 | 168.9 (1) |
N1—N2—C9—C8 | −0.9 (1) | C24—O2—C21—C22 | −12.7 (2) |
N1—N2—C9—C10 | −179.3 (1) | C19—C20—C21—O2 | 178.9 (1) |
C11—C8—C9—N2 | −173.7 (1) | C19—C20—C21—C22 | 0.4 (2) |
C7—C8—C9—N2 | −1.0 (1) | O2—C21—C22—C23 | −179.4 (1) |
C11—C8—C9—C10 | 4.4 (2) | C20—C21—C22—C23 | −1.1 (2) |
C7—C8—C9—C10 | 177.1 (1) | C19—C18—C23—C22 | 0.1 (2) |
C18—N3—C11—C8 | 175.4 (1) | N3—C18—C23—C22 | 178.9 (1) |
C18—N3—C11—C12 | −8.2 (2) | C21—C22—C23—C18 | 0.8 (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) | 1.96 (1) | 2.714 (1) | 145 (2) |