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organic compounds
The NH unit on the exocyclic carbon-carbon double bond in the title compound, C24H21N3O, lies on the same side of the double bond as the carbonyl unit of the pyrazolonyl ring, and the two interact through an N—HO hydrogen bond [2.714 (2) Å].
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804013479/bt6466sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804013479/bt6466Isup2.hkl |
CCDC reference: 245281
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.134
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Expl .... -P 2yc PLAT157_ALERT_4_C Non-standard Monoclinic Beta Angle less 90 Deg 79.61 Deg.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
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: ORTEP-I (Johnson, 1976); software used to prepare material for publication: SHELXL97.
5-Methyl-2-phenyl-4-[(Z)-(benzylaminophenylmethylene]-2H-pyrazol-3-one top
Crystal data top
C24H21N3O | F(000) = 776 |
Mr = 367.44 | Dx = 1.264 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yc | Cell parameters from 872 reflections |
a = 8.912 (1) Å | θ = 2.5–25.9° |
b = 20.769 (3) Å | µ = 0.08 mm−1 |
c = 10.608 (1) Å | T = 293 K |
β = 79.605 (2)° | Prism, yellow |
V = 1931.2 (4) Å3 | 0.50 × 0.38 × 0.14 mm |
Z = 4 |
Data collection top
Bruker SMART area-detector diffractometer | 2456 reflections with I > 2σ(I) |
Radiation source: medium-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 27.2°, θmin = 2.0° |
φ and ω scan | h = −11→11 |
11972 measured reflections | k = −26→23 |
4250 independent reflections | l = −10→13 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0631P)2 + 0.2452P] where P = (Fo2 + 2Fc2)/3 |
4250 reflections | (Δ/σ)max = 0.001 |
258 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.3582 (2) | 0.5724 (1) | 0.4401 (1) | 0.0632 (4) | |
N1 | 0.1820 (2) | 0.5698 (1) | 0.6325 (1) | 0.0516 (4) | |
N2 | 0.0823 (2) | 0.5248 (1) | 0.7012 (1) | 0.0549 (4) | |
N3 | 0.3726 (2) | 0.4549 (1) | 0.3266 (1) | 0.0533 (4) | |
C1 | 0.1996 (2) | 0.6307 (1) | 0.6869 (2) | 0.0531 (5) | |
C2 | 0.1373 (2) | 0.6415 (1) | 0.8149 (2) | 0.0678 (6) | |
C3 | 0.1592 (3) | 0.7011 (1) | 0.8682 (2) | 0.0861 (8) | |
C4 | 0.2420 (3) | 0.7489 (1) | 0.7963 (3) | 0.0920 (8) | |
C5 | 0.3014 (3) | 0.7374 (1) | 0.6718 (2) | 0.0876 (7) | |
C6 | 0.2809 (3) | 0.6789 (1) | 0.6160 (2) | 0.0706 (6) | |
C7 | 0.2635 (2) | 0.5435 (1) | 0.5216 (2) | 0.0493 (4) | |
C8 | 0.2155 (2) | 0.4776 (1) | 0.5234 (2) | 0.0461 (4) | |
C9 | 0.1021 (2) | 0.4711 (1) | 0.6363 (2) | 0.0495 (4) | |
C10 | 0.0063 (2) | 0.4144 (1) | 0.6839 (2) | 0.0689 (6) | |
C11 | 0.2801 (2) | 0.4337 (1) | 0.4296 (2) | 0.0449 (4) | |
C12 | 0.2546 (2) | 0.3635 (1) | 0.4431 (2) | 0.0481 (4) | |
C13 | 0.1705 (2) | 0.3309 (1) | 0.3667 (2) | 0.0655 (5) | |
C14 | 0.1533 (3) | 0.2654 (1) | 0.3789 (3) | 0.0864 (8) | |
C15 | 0.2203 (3) | 0.2322 (1) | 0.4658 (3) | 0.0904 (8) | |
C16 | 0.3037 (3) | 0.2645 (1) | 0.5415 (2) | 0.0848 (7) | |
C17 | 0.3209 (2) | 0.3298 (1) | 0.5312 (2) | 0.0647 (5) | |
C18 | 0.4638 (2) | 0.4171 (1) | 0.2261 (2) | 0.0495 (4) | |
C19 | 0.4168 (2) | 0.4230 (1) | 0.0969 (2) | 0.0423 (4) | |
C20 | 0.5198 (2) | 0.4028 (1) | −0.0096 (2) | 0.0506 (4) | |
C21 | 0.4847 (2) | 0.4074 (1) | −0.1305 (2) | 0.0589 (5) | |
C22 | 0.3490 (3) | 0.4334 (1) | −0.1470 (2) | 0.0616 (5) | |
C23 | 0.2459 (2) | 0.4532 (1) | −0.0424 (2) | 0.0600 (5) | |
C24 | 0.2787 (2) | 0.4479 (1) | 0.0796 (2) | 0.0514 (4) | |
H3n | 0.389 (2) | 0.496 (1) | 0.327 (1) | 0.065 (6)* | |
H2 | 0.0820 | 0.6094 | 0.8639 | 0.081* | |
H3 | 0.1175 | 0.7090 | 0.9536 | 0.103* | |
H4 | 0.2568 | 0.7885 | 0.8331 | 0.110* | |
H5 | 0.3570 | 0.7695 | 0.6230 | 0.105* | |
H6 | 0.3222 | 0.6720 | 0.5301 | 0.085* | |
H10a | 0.0688 | 0.3819 | 0.7131 | 0.103* | |
H10b | −0.0395 | 0.3972 | 0.6158 | 0.103* | |
H10c | −0.0723 | 0.4273 | 0.7536 | 0.103* | |
H13 | 0.1256 | 0.3532 | 0.3071 | 0.079* | |
H14 | 0.0959 | 0.2433 | 0.3278 | 0.104* | |
H15 | 0.2089 | 0.1878 | 0.4732 | 0.108* | |
H16 | 0.3491 | 0.2419 | 0.6004 | 0.102* | |
H17 | 0.3773 | 0.3516 | 0.5834 | 0.078* | |
H18a | 0.4574 | 0.3722 | 0.2516 | 0.059* | |
H18b | 0.5695 | 0.4302 | 0.2179 | 0.059* | |
H20 | 0.6135 | 0.3859 | 0.0006 | 0.061* | |
H21 | 0.5537 | 0.3929 | −0.2011 | 0.071* | |
H22 | 0.3265 | 0.4377 | −0.2288 | 0.074* | |
H23 | 0.1528 | 0.4704 | −0.0536 | 0.072* | |
H24 | 0.2077 | 0.4612 | 0.1500 | 0.062* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.085 (1) | 0.055 (1) | 0.045 (1) | −0.006 (1) | 0.001 (1) | −0.004 (1) |
N1 | 0.060 (1) | 0.056 (1) | 0.039 (1) | 0.009 (1) | −0.008 (1) | −0.004 (1) |
N2 | 0.054 (1) | 0.066 (1) | 0.044 (1) | 0.010 (1) | −0.007 (1) | −0.002 (1) |
N3 | 0.074 (1) | 0.046 (1) | 0.038 (1) | 0.004 (1) | −0.006 (1) | −0.001 (1) |
C1 | 0.059 (1) | 0.059 (1) | 0.045 (1) | 0.020 (1) | −0.020 (1) | −0.013 (1) |
C2 | 0.059 (1) | 0.088 (2) | 0.057 (1) | 0.013 (1) | −0.012 (1) | −0.020 (1) |
C3 | 0.078 (2) | 0.115 (2) | 0.067 (2) | 0.020 (2) | −0.014 (1) | −0.045 (2) |
C4 | 0.110 (2) | 0.078 (2) | 0.093 (2) | 0.014 (2) | −0.029 (2) | −0.035 (2) |
C5 | 0.130 (2) | 0.060 (1) | 0.077 (2) | 0.007 (1) | −0.028 (2) | −0.014 (1) |
C6 | 0.106 (2) | 0.056 (1) | 0.052 (1) | 0.014 (1) | −0.022 (1) | −0.005 (1) |
C7 | 0.058 (1) | 0.054 (1) | 0.036 (1) | 0.009 (1) | −0.010 (1) | −0.002 (1) |
C8 | 0.052 (1) | 0.052 (1) | 0.036 (1) | 0.005 (1) | −0.013 (1) | 0.000 (1) |
C9 | 0.047 (1) | 0.060 (1) | 0.043 (1) | 0.006 (1) | −0.012 (1) | 0.0042 (1) |
C10 | 0.061 (1) | 0.077 (2) | 0.065 (1) | −0.002 (1) | −0.003 (1) | 0.003 (1) |
C11 | 0.051 (1) | 0.051 (1) | 0.036 (1) | 0.003 (1) | −0.015 (1) | 0.002 (1) |
C12 | 0.052 (1) | 0.048 (1) | 0.044 (1) | 0.003 (1) | −0.007 (1) | 0.000 (1) |
C13 | 0.066 (1) | 0.067 (1) | 0.065 (1) | −0.010 (1) | −0.015 (1) | −0.002 (1) |
C14 | 0.089 (2) | 0.072 (2) | 0.092 (2) | −0.026 (1) | 0.000 (2) | −0.016 (1) |
C15 | 0.099 (2) | 0.046 (1) | 0.111 (2) | 0.000 (1) | 0.022 (2) | 0.001 (1) |
C16 | 0.096 (2) | 0.062 (2) | 0.091 (2) | 0.018 (1) | −0.002 (2) | 0.020 (1) |
C17 | 0.077 (1) | 0.059 (1) | 0.059 (1) | 0.010 (1) | −0.017 (1) | 0.006 (1) |
C18 | 0.057 (1) | 0.051 (1) | 0.040 (1) | 0.008 (1) | −0.006 (1) | −0.001 (1) |
C19 | 0.052 (1) | 0.036 (1) | 0.039 (1) | 0.001 (1) | −0.007 (1) | 0.001 (1) |
C20 | 0.055 (1) | 0.050 (1) | 0.046 (1) | 0.006 (1) | −0.007 (1) | −0.001 (1) |
C21 | 0.077 (1) | 0.057 (1) | 0.040 (1) | 0.000 (1) | −0.004 (1) | −0.003 (1) |
C22 | 0.087 (2) | 0.056 (1) | 0.047 (1) | −0.005 (1) | −0.026 (1) | 0.003 (1) |
C23 | 0.066 (1) | 0.056 (1) | 0.065 (1) | 0.005 (1) | −0.028 (1) | 0.002 (1) |
C24 | 0.056 (1) | 0.047 (1) | 0.051 (1) | 0.006 (1) | −0.009 (1) | −0.002 (1) |
Geometric parameters (Å, º) top
O1—C7 | 1.247 (2) | C19—C20 | 1.386 (2) |
N1—C7 | 1.379 (2) | C20—C21 | 1.377 (2) |
N1—N2 | 1.399 (2) | C21—C22 | 1.364 (3) |
N1—C1 | 1.412 (2) | C22—C23 | 1.369 (3) |
N2—C9 | 1.306 (2) | C23—C24 | 1.382 (2) |
N3—C11 | 1.321 (2) | N3—H3N | 0.87 (2) |
N3—C18 | 1.450 (2) | C2—H2 | 0.93 |
C1—C6 | 1.377 (3) | C3—H3 | 0.93 |
C1—C2 | 1.389 (2) | C4—H4 | 0.93 |
C2—C3 | 1.390 (3) | C5—H5 | 0.93 |
C3—C4 | 1.381 (4) | C6—H6 | 0.93 |
C4—C5 | 1.353 (3) | C10—H10a | 0.96 |
C5—C6 | 1.377 (3) | C10—H10b | 0.96 |
C7—C8 | 1.434 (3) | C10—H10c | 0.96 |
C8—C11 | 1.395 (2) | C13—H13 | 0.93 |
C8—C9 | 1.428 (2) | C14—H14 | 0.93 |
C9—C10 | 1.489 (3) | C15—H15 | 0.93 |
C11—C12 | 1.478 (2) | C16—H16 | 0.93 |
C12—C13 | 1.376 (3) | C17—H17 | 0.93 |
C12—C17 | 1.382 (2) | C18—H18a | 0.97 |
C13—C14 | 1.373 (3) | C18—H18b | 0.97 |
C14—C15 | 1.371 (4) | C20—H20 | 0.93 |
C15—C16 | 1.365 (4) | C21—H21 | 0.93 |
C16—C17 | 1.368 (3) | C22—H22 | 0.93 |
C18—C19 | 1.508 (2) | C23—H23 | 0.93 |
C19—C24 | 1.378 (2) | C24—H24 | 0.93 |
C7—N1—N2 | 111.6 (1) | C18—N3—H3n | 118 (1) |
C7—N1—C1 | 128.5 (2) | C3—C2—H2 | 120.6 |
N2—N1—C1 | 119.5 (1) | C1—C2—H2 | 120.6 |
C9—N2—N1 | 106.5 (1) | C4—C3—H3 | 119.5 |
C11—N3—C18 | 127.6 (2) | C2—C3—H3 | 119.5 |
C6—C1—N1 | 121.0 (2) | C5—C4—H4 | 120.4 |
C2—C1—N1 | 119.3 (2) | C3—C4—H4 | 120.4 |
C6—C1—C2 | 119.7 (2) | C4—C5—H5 | 119.5 |
C3—C2—C1 | 118.7 (2) | C6—C5—H5 | 119.5 |
C4—C3—C2 | 121.0 (2) | C1—C6—H6 | 119.9 |
C5—C4—C3 | 119.2 (2) | C5—C6—H6 | 119.9 |
C4—C5—C6 | 121.1 (3) | C9—C10—H10a | 109.5 |
C1—C6—C5 | 120.3 (2) | C9—C10—H10b | 109.5 |
O1—C7—N1 | 126.0 (2) | H10a—C10—H10b | 109.5 |
O1—C7—C8 | 129.2 (2) | C9—C10—H10c | 109.5 |
N1—C7—C8 | 104.9 (2) | H10a—C10—H10c | 109.5 |
C11—C8—C9 | 132.5 (2) | H10b—C10—H10c | 109.5 |
C11—C8—C7 | 122.1 (2) | C14—C13—H13 | 120.2 |
C9—C8—C7 | 105.4 (1) | C12—C13—H13 | 120.2 |
N2—C9—C8 | 111.7 (2) | C13—C14—H14 | 119.8 |
N2—C9—C10 | 118.9 (2) | C15—C14—H14 | 119.8 |
C8—C9—C10 | 129.4 (2) | C16—C15—H15 | 120.0 |
N3—C11—C8 | 119.2 (2) | C14—C15—H15 | 120.0 |
N3—C11—C12 | 118.2 (2) | C15—C16—H16 | 119.8 |
C8—C11—C12 | 122.6 (2) | C17—C16—H16 | 119.8 |
C13—C12—C11 | 121.3 (2) | C16—C17—H17 | 120.0 |
C17—C12—C11 | 119.1 (2) | C12—C17—H17 | 120.0 |
C13—C12—C17 | 119.6 (2) | N3—C18—H18a | 108.7 |
C14—C13—C12 | 119.7 (2) | C19—C18—H18a | 108.7 |
C13—C14—C15 | 120.4 (2) | N3—C18—H18b | 108.7 |
C16—C15—C14 | 119.9 (2) | C19—C18—H18b | 108.7 |
C15—C16—C17 | 120.3 (2) | H18a—C18—H18b | 107.6 |
C16—C17—C12 | 120.0 (2) | C21—C20—H20 | 119.7 |
N3—C18—C19 | 114.4 (1) | C19—C20—H20 | 119.7 |
C24—C19—C18 | 123.5 (2) | C22—C21—H21 | 119.9 |
C20—C19—C18 | 117.7 (2) | C20—C21—H21 | 119.9 |
C24—C19—C20 | 118.8 (2) | C21—C22—H22 | 120.1 |
C21—C20—C19 | 120.6 (2) | C23—C22—H22 | 120.1 |
C22—C21—C20 | 120.2 (2) | C22—C23—H23 | 119.7 |
C21—C22—C23 | 119.7 (2) | C24—C23—H23 | 119.7 |
C22—C23—C24 | 120.7 (2) | C19—C24—H24 | 120.0 |
C19—C24—C23 | 120.0 (2) | C23—C24—H24 | 120.0 |
C11—N3—H3n | 114 (1) | ||
C7—N1—N2—C9 | 0.9 (2) | C18—N3—C11—C12 | −4.9 (3) |
C1—N1—N2—C9 | −172.6 (1) | C9—C8—C11—N3 | 172.7 (2) |
C7—N1—C1—C6 | 16.2 (3) | C7—C8—C11—N3 | −9.7 (2) |
N2—N1—C1—C6 | −171.6 (2) | C9—C8—C11—C12 | −10.0 (3) |
C7—N1—C1—C2 | −162.0 (2) | C7—C8—C11—C12 | 167.7 (2) |
N2—N1—C1—C2 | 10.2 (2) | N3—C11—C12—C13 | −71.2 (2) |
C6—C1—C2—C3 | 0.0 (3) | C8—C11—C12—C13 | 111.4 (2) |
N1—C1—C2—C3 | 178.2 (2) | N3—C11—C12—C17 | 106.6 (2) |
C1—C2—C3—C4 | −0.4 (3) | C8—C11—C12—C17 | −70.8 (2) |
C2—C3—C4—C5 | 0.5 (4) | C17—C12—C13—C14 | 0.1 (3) |
C3—C4—C5—C6 | −0.2 (4) | C11—C12—C13—C14 | 177.9 (2) |
C2—C1—C6—C5 | 0.4 (3) | C12—C13—C14—C15 | −0.5 (3) |
N1—C1—C6—C5 | −177.8 (2) | C13—C14—C15—C16 | 0.5 (4) |
C4—C5—C6—C1 | −0.3 (4) | C14—C15—C16—C17 | 0.0 (4) |
N2—N1—C7—O1 | 178.4 (2) | C15—C16—C17—C12 | −0.5 (3) |
C1—N1—C7—O1 | −8.8 (3) | C13—C12—C17—C16 | 0.4 (3) |
N2—N1—C7—C8 | −2.0 (2) | C11—C12—C17—C16 | −177.4 (2) |
C1—N1—C7—C8 | 170.8 (2) | C11—N3—C18—C19 | 113.9 (2) |
O1—C7—C8—C11 | 3.6 (3) | N3—C18—C19—C24 | −15.9 (2) |
N1—C7—C8—C11 | −176.0 (2) | N3—C18—C19—C20 | 163.3 (2) |
O1—C7—C8—C9 | −178.2 (2) | C24—C19—C20—C21 | −0.1 (3) |
N1—C7—C8—C9 | 2.2 (2) | C18—C19—C20—C21 | −179.3 (2) |
N1—N2—C9—C8 | 0.6 (2) | C19—C20—C21—C22 | 1.4 (3) |
N1—N2—C9—C10 | −177.8 (2) | C20—C21—C22—C23 | −1.8 (3) |
C11—C8—C9—N2 | 176.2 (2) | C21—C22—C23—C24 | 0.9 (3) |
C7—C8—C9—N2 | −1.7 (2) | C20—C19—C24—C23 | −0.8 (3) |
C11—C8—C9—C10 | −5.8 (3) | C18—C19—C24—C23 | 178.4 (2) |
C7—C8—C9—C10 | 176.3 (2) | C22—C23—C24—C19 | 0.5 (3) |
C18—N3—C11—C8 | 172.6 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3n···O1 | 0.87 (2) | 1.98 (2) | 2.714 (2) | 142 (2) |
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