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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—H...O hydrogen bond [2.695 (2) Å].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803029258/wk6006sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803029258/wk6006Isup2.hkl
Contains datablock I

CCDC reference: 234837

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.133
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.90 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C22 - C23 = 5.60 su PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C23
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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: 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
C24H21N3OZ = 2
Mr = 367.44F(000) = 388
Triclinic, P1Dx = 1.217 Mg m3
a = 9.792 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.832 (1) ÅCell parameters from 848 reflections
c = 11.556 (2) Åθ = 2.5–26.5°
α = 101.560 (2)°µ = 0.08 mm1
β = 99.974 (2)°T = 298 K
γ = 108.034 (2)°Block, yellow
V = 1002.9 (2) Å30.50 × 0.35 × 0.20 mm
Data collection top
Bruker SMART area-detector
diffractometer
2832 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.012
Graphite monochromatorθmax = 27.1°, θmin = 1.9°
φ and ω scansh = 1212
8614 measured reflectionsk = 1212
4346 independent reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: mixed
wR(F2) = 0.133H 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 parametersΔρmax = 0.15 e Å3
1 restraintΔρmin = 0.14 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.6974 (1)0.6541 (1)0.4937 (1)0.0671 (3)
N10.8513 (1)0.8087 (1)0.6838 (1)0.0587 (3)
N21.0030 (1)0.8909 (2)0.7332 (1)0.0660 (4)
N30.8634 (2)0.6158 (2)0.3355 (1)0.0633 (4)
C10.7521 (2)0.8179 (2)0.7585 (1)0.0581 (4)
C20.8022 (2)0.9241 (2)0.8695 (2)0.0707 (5)
C30.7046 (2)0.9353 (2)0.9410 (2)0.0852 (6)
C40.5601 (2)0.8440 (3)0.9044 (2)0.0868 (6)
C50.5114 (2)0.7390 (2)0.7945 (2)0.0884 (6)
C60.6061 (2)0.7234 (2)0.7212 (2)0.0778 (5)
C70.8215 (2)0.7327 (2)0.5632 (1)0.0535 (4)
C80.9650 (2)0.7643 (2)0.5370 (1)0.0527 (4)
C91.0685 (2)0.8640 (2)0.6471 (2)0.0603 (4)
C101.2334 (2)0.9366 (2)0.6729 (2)0.0914 (6)
C110.9832 (2)0.7019 (2)0.4244 (1)0.0506 (3)
C121.1329 (2)0.7298 (2)0.4011 (1)0.0509 (3)
C131.1910 (2)0.8400 (2)0.3475 (2)0.0655 (4)
C141.3332 (2)0.8700 (2)0.3322 (2)0.0812 (5)
C151.4147 (2)0.7884 (2)0.3678 (2)0.0819 (6)
C161.3573 (2)0.6774 (2)0.4196 (2)0.0795 (5)
C171.2171 (2)0.6493 (2)0.4376 (2)0.0676 (4)
C180.8563 (2)0.5327 (2)0.2168 (1)0.0604 (4)
C190.9211 (2)0.4264 (2)0.2043 (2)0.0755 (5)
C200.9094 (3)0.3416 (3)0.0913 (2)0.1009 (7)
C210.8326 (3)0.3614 (3)0.0081 (2)0.1103 (8)
C220.7658 (3)0.4644 (3)0.0019 (2)0.1074 (8)
C230.7766 (2)0.5548 (2)0.1169 (2)0.0829 (5)
C240.7038 (4)0.6685 (4)0.1313 (3)0.147 (1)
H3n0.781 (1)0.610 (2)0.357 (2)0.087 (6)*
H20.90090.98760.89610.085*
H30.73871.00701.01570.102*
H40.49550.85270.95320.104*
H50.41230.67660.76840.106*
H60.57160.64980.64750.093*
H10a1.25690.99620.61760.137*
H10b1.27740.86170.66220.137*
H10c1.27180.99860.75540.137*
H131.13480.89420.32170.079*
H141.37340.94590.29760.097*
H151.51000.80850.35660.098*
H161.41270.62120.44260.095*
H171.17880.57540.47480.081*
H190.97320.41220.27340.091*
H200.95430.27070.08320.121*
H210.82480.30380.08500.132*
H220.71220.47520.06820.129*
H24a0.62840.64080.17430.220*
H24b0.65950.67380.05220.220*
H24c0.77680.76370.17660.220*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0431 (6)0.0806 (8)0.0691 (7)0.0190 (5)0.0118 (5)0.0092 (6)
N10.0472 (7)0.0632 (8)0.0622 (8)0.0178 (6)0.0167 (6)0.0099 (6)
N20.0506 (7)0.0701 (9)0.0672 (8)0.0150 (6)0.0149 (6)0.0067 (7)
N30.0462 (7)0.0766 (9)0.0609 (8)0.0192 (7)0.0137 (6)0.0090 (7)
C10.058 (1)0.062 (1)0.064 (1)0.026 (1)0.023 (1)0.022 (1)
C20.073 (1)0.076 (1)0.065 (1)0.026 (1)0.025 (1)0.018 (1)
C30.100 (2)0.091 (1)0.074 (1)0.037 (1)0.042 (1)0.020 (1)
C40.094 (2)0.100 (2)0.093 (2)0.045 (1)0.056 (1)0.037 (1)
C50.067 (1)0.099 (2)0.103 (2)0.023 (1)0.041 (1)0.028 (1)
C60.063 (1)0.083 (1)0.083 (1)0.019 (1)0.031 (1)0.013 (1)
C70.047 (1)0.054 (1)0.061 (1)0.019 (1)0.013 (1)0.014 (1)
C80.045 (1)0.052 (1)0.060 (1)0.018 (1)0.015 (1)0.014 (1)
C90.047 (1)0.059 (1)0.068 (1)0.014 (1)0.015 (1)0.010 (1)
C100.053 (1)0.099 (1)0.088 (1)0.003 (1)0.017 (1)0.010 (1)
C110.047 (1)0.048 (1)0.060 (1)0.019 (1)0.014 (1)0.018 (1)
C120.047 (1)0.050 (1)0.056 (1)0.016 (1)0.015 (1)0.013 (1)
C130.061 (1)0.066 (1)0.075 (1)0.021 (1)0.021 (1)0.030 (1)
C140.066 (1)0.085 (1)0.094 (1)0.013 (1)0.034 (1)0.039 (1)
C150.050 (1)0.093 (1)0.096 (1)0.016 (1)0.028 (1)0.018 (1)
C160.055 (1)0.081 (1)0.109 (2)0.033 (1)0.022 (1)0.025 (1)
C170.055 (1)0.066 (1)0.092 (1)0.025 (1)0.023 (1)0.033 (1)
C180.052 (1)0.062 (1)0.058 (1)0.010 (1)0.015 (1)0.013 (1)
C190.074 (1)0.071 (1)0.077 (1)0.024 (1)0.020 (1)0.011 (1)
C200.099 (2)0.088 (2)0.098 (2)0.025 (1)0.031 (1)0.006 (1)
C210.110 (2)0.114 (2)0.076 (2)0.014 (2)0.031 (1)0.004 (1)
C220.106 (2)0.123 (2)0.066 (1)0.014 (2)0.002 (1)0.026 (1)
C230.079 (1)0.088 (1)0.072 (1)0.020 (1)0.007 (1)0.025 (1)
C240.167 (3)0.151 (3)0.130 (2)0.091 (2)0.012 (2)0.041 (2)
Geometric parameters (Å, º) top
O1—C71.245 (2)C19—C201.366 (3)
N1—C71.376 (2)C20—C211.343 (4)
N1—N21.402 (2)C21—C221.362 (4)
N1—C11.418 (2)C22—C231.410 (3)
N2—C91.300 (2)C23—C241.498 (3)
N3—C111.329 (2)N3—H3n0.87 (1)
N3—C181.427 (2)C2—H20.93
C1—C61.377 (2)C3—H30.93
C1—C21.380 (2)C4—H40.93
C2—C31.381 (2)C5—H50.93
C3—C41.357 (3)C6—H60.93
C4—C51.366 (3)C10—H10a0.96
C5—C61.382 (3)C10—H10b0.96
C7—C81.441 (2)C10—H10c0.96
C8—C91.430 (2)C13—H130.93
C8—C111.390 (2)C14—H140.93
C9—C101.497 (2)C15—H150.93
C11—C121.488 (2)C16—H160.93
C12—C131.375 (2)C17—H170.93
C12—C171.379 (2)C19—H190.93
C13—C141.381 (2)C20—H200.93
C14—C151.366 (3)C21—H210.93
C15—C161.365 (3)C22—H220.93
C16—C171.375 (2)C24—H24a0.96
C18—C191.377 (2)C24—H24b0.96
C18—C231.373 (2)C24—H24c0.96
N2—N1—C7111.9 (1)C11—N3—H3n113 (1)
N2—N1—C1118.6 (1)C18—N3—H3n119 (1)
C1—N1—C7129.5 (1)C3—C2—H2120.3
N1—N2—C9106.5 (1)C1—C2—H2120.3
C11—N3—C18128.3 (1)C4—C3—H3119.3
N1—C1—C2119.5 (2)C2—C3—H3119.3
N1—C1—C6120.9 (2)C3—C4—H4120.6
C2—C1—C6119.6 (2)C5—C4—H4120.6
C3—C2—C1119.5 (2)C4—C5—H5119.3
C4—C3—C2121.4 (2)C6—C5—H5119.3
C3—C4—C5118.8 (2)C1—C6—H6120.4
C4—C5—C6121.5 (2)C5—C6—H6120.4
C1—C6—C5119.3 (2)C9—C10—H10a109.5
O1—C7—N1127.0 (1)C9—C10—H10b109.5
O1—C7—C8128.5 (1)H10a—C10—H10b109.5
N1—C7—C8104.5 (1)C9—C10—H10c109.5
C7—C8—C9105.3 (1)H10a—C10—H10c109.5
C7—C8—C11122.4 (1)H10b—C10—H10c109.5
C9—C8—C11132.3 (1)C12—C13—H13120.1
N2—C9—C8111.8 (1)C14—C13—H13120.1
N2—C9—C10119.0 (2)C15—C14—H14119.9
C8—C9—C10129.2 (2)C13—C14—H14119.9
N3—C11—C8118.9 (1)C16—C15—H15119.8
N3—C11—C12119.5 (1)C14—C15—H15119.8
C8—C11—C12121.6 (1)C15—C16—H16120.2
C13—C12—C17119.4 (1)C17—C16—H16120.2
C11—C12—C13120.3 (1)C16—C17—H17119.7
C11—C12—C17120.2 (1)C12—C17—H17119.7
C12—C13—C14119.8 (2)C20—C19—H19119.7
C13—C14—C15120.2 (2)C18—C19—H19119.7
C14—C15—C16120.5 (2)C21—C20—H20120.3
C15—C16—C17119.6 (2)C19—C20—H20120.3
C12—C17—C17120.5 (2)C20—C21—H21119.4
C19—C18—C23121.2 (2)C22—C21—H21119.4
N3—C18—C23118.6 (2)C21—C22—H22119.5
N3—C18—C19120.1 (2)C23—C22—H22119.5
C18—C19—C20120.6 (2)C23—C24—H24a109.5
C19—C20—C21119.5 (2)C23—C24—H24b109.5
C20—C21—C22121.1 (2)H24a—C24—H24b109.5
C21—C22—C23121.0 (2)C23—C24—H24c109.5
C18—C23—C22116.6 (2)H24a—C24—H24c109.5
C18—C23—C24120.9 (2)H24b—C24—H24c109.5
C22—C23—C24122.4 (2)
C7—N1—N2—C91.9 (2)C9—C8—C11—N3177.3 (2)
C1—N1—N2—C9179.7 (1)C7—C8—C11—N33.5 (2)
C7—N1—C1—C612.4 (3)C9—C8—C11—C122.5 (2)
N2—N1—C1—C6170.2 (2)C7—C8—C11—C12176.8 (1)
C7—N1—C1—C2166.9 (2)N3—C11—C12—C1384.0 (2)
N2—N1—C1—C210.5 (2)C8—C11—C12—C1395.7 (2)
C6—C1—C2—C30.8 (3)N3—C11—C12—C1798.6 (2)
N1—C1—C2—C3178.4 (2)C8—C11—C12—C1781.7 (2)
C1—C2—C3—C40.0 (3)C17—C12—C13—C140.7 (3)
C2—C3—C4—C50.1 (3)C11—C12—C13—C14176.6 (2)
C3—C4—C5—C60.6 (3)C12—C13—C14—C151.4 (3)
C2—C1—C6—C51.5 (3)C13—C14—C15—C160.5 (3)
N1—C1—C6—C5177.8 (2)C14—C15—C16—C170.9 (3)
C4—C5—C6—C11.4 (3)C15—C16—C17—C121.6 (3)
N2—N1—C7—O1177.6 (1)C13—C12—C17—C160.7 (3)
C1—N1—C7—O10.2 (3)C11—C12—C17—C16178.1 (2)
N2—N1—C7—C82.6 (2)C11—N3—C18—C23125.3 (2)
C1—N1—C7—C8179.9 (1)C11—N3—C18—C1958.6 (2)
O1—C7—C8—C112.6 (2)C23—C18—C19—C201.1 (3)
N1—C7—C8—C11177.1 (1)N3—C18—C19—C20177.1 (2)
O1—C7—C8—C9178.0 (2)C18—C19—C20—C210.7 (3)
N1—C7—C8—C92.3 (2)C19—C20—C21—C220.1 (4)
N1—N2—C9—C80.3 (2)C20—C21—C22—C230.7 (4)
N1—N2—C9—C10179.8 (2)C19—C18—C23—C220.5 (3)
C11—C8—C9—N2178.1 (2)N3—C18—C23—C22176.6 (2)
C7—C8—C9—N21.3 (2)C19—C18—C23—C24178.7 (2)
C11—C8—C9—C102.0 (3)N3—C18—C23—C242.7 (3)
C7—C8—C9—C10178.6 (2)C21—C22—C23—C180.4 (3)
C18—N3—C11—C8175.1 (2)C21—C22—C23—C24179.6 (3)
C18—N3—C11—C125.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3n···O10.87 (1)1.94 (1)2.695 (2)144 (2)
 

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