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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 [N...O = 2.714 (1) Å].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680402728X/bt6554sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680402728X/bt6554Isup2.hkl
Contains datablock I

CCDC reference: 259099

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.040
  • wR factor = 0.124
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ? PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 52.00 A   3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 1 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, 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
C24H21N3O2Z = 2
Mr = 383.44F(000) = 404
Triclinic, P1Dx = 1.261 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.8262 (9) ÅCell parameters from 904 reflections
b = 10.951 (1) Åθ = 2.0–27.1°
c = 14.761 (1) ŵ = 0.08 mm1
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 tubeRint = 0.013
Graphite monochromatorθmax = 27.1°, θmin = 2.0°
φ and ω scansh = 88
8643 measured reflectionsk = 1313
4350 independent reflectionsl = 1818
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H 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 parametersΔρmax = 0.15 e Å3
1 restraintΔρmin = 0.19 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5354 (2)0.6041 (1)0.7503 (1)0.0563 (3)
O21.1065 (2)0.2880 (1)0.4206 (1)0.0703 (3)
N10.3569 (2)0.5293 (1)0.8597 (1)0.0502 (3)
N20.2916 (2)0.4135 (1)0.8910 (1)0.0533 (3)
N30.6537 (2)0.4113 (1)0.6670 (1)0.0518 (3)
C10.2788 (2)0.6313 (1)0.8864 (1)0.0521 (3)
C20.3840 (3)0.7573 (1)0.8827 (1)0.0628 (4)
C30.3027 (4)0.8552 (2)0.9082 (1)0.0786 (5)
C40.1207 (4)0.8285 (2)0.9373 (1)0.0857 (6)
C50.0179 (3)0.7033 (2)0.9414 (1)0.0789 (5)
C60.0961 (3)0.6041 (2)0.9159 (1)0.0637 (4)
C70.4706 (2)0.5197 (1)0.7949 (1)0.0460 (3)
C80.4872 (2)0.3905 (1)0.7890 (1)0.0449 (3)
C90.3697 (2)0.3331 (1)0.8502 (1)0.0479 (3)
C100.3232 (3)0.1993 (1)0.8697 (1)0.0628 (4)
C110.5816 (2)0.3399 (1)0.7259 (1)0.0449 (3)
C120.5937 (2)0.2059 (1)0.7174 (1)0.0481 (3)
C130.7182 (2)0.1699 (2)0.7903 (1)0.0647 (4)
C140.7220 (3)0.0435 (2)0.7806 (2)0.0810 (5)
C150.6023 (3)0.0462 (2)0.6993 (2)0.0841 (5)
C160.4808 (3)0.0109 (2)0.6263 (1)0.0790 (5)
C170.4764 (2)0.1151 (1)0.6344 (1)0.0612 (4)
C180.7670 (2)0.3783 (1)0.6026 (1)0.0469 (3)
C190.9546 (2)0.3520 (1)0.6354 (1)0.0558 (3)
C201.0618 (2)0.3212 (2)0.5723 (1)0.0593 (4)
C210.9851 (2)0.3174 (1)0.4765 (1)0.0502 (3)
C220.7992 (2)0.3455 (1)0.4434 (1)0.0489 (3)
C230.6906 (2)0.3751 (1)0.5071 (1)0.0484 (3)
C241.0161 (3)0.2602 (2)0.3208 (1)0.0798 (5)
H3n0.635 (3)0.487 (1)0.675 (1)0.069 (5)*
H20.50750.77610.86330.075*
H30.37210.94010.90560.094*
H40.06760.89490.95420.103*
H50.10480.68500.96130.095*
H60.02610.51940.91870.076*
H10a0.22710.18790.90850.094*
H10b0.45280.18670.90240.094*
H10c0.25970.13720.81060.094*
H130.79920.23040.84570.078*
H140.80620.01910.82960.097*
H150.60380.13140.69380.101*
H160.40100.07190.57100.095*
H170.39500.13930.58430.073*
H191.00800.35500.69980.067*
H201.18740.30280.59440.071*
H220.74770.34460.37910.059*
H230.56440.39300.48510.058*
H24a0.88930.18690.30350.120*
H24b1.11590.24080.28960.120*
H24c0.98200.33410.30160.120*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.069 (1)0.047 (1)0.063 (1)0.022 (1)0.028 (1)0.020 (1)
O20.061 (1)0.092 (1)0.063 (1)0.033 (1)0.021 (1)0.004 (1)
N10.064 (1)0.041 (1)0.051 (1)0.019 (1)0.021 (1)0.011 (1)
N20.067 (1)0.046 (1)0.052 (1)0.020 (1)0.023 (1)0.015 (1)
N30.061 (1)0.045 (1)0.059 (1)0.023 (1)0.025 (1)0.015 (1)
C10.068 (1)0.049 (1)0.042 (1)0.026 (1)0.014 (1)0.005 (1)
C20.084 (1)0.048 (1)0.057 (1)0.025 (1)0.018 (1)0.008 (1)
C30.121 (2)0.054 (1)0.064 (1)0.040 (1)0.019 (1)0.008 (1)
C40.130 (2)0.082 (1)0.064 (1)0.069 (1)0.026 (1)0.006 (1)
C50.099 (1)0.093 (1)0.064 (1)0.054 (1)0.032 (1)0.010 (1)
C60.078 (1)0.063 (1)0.057 (1)0.029 (1)0.026 (1)0.009 (1)
C70.050 (1)0.042 (1)0.045 (1)0.015 (1)0.010 (1)0.008 (1)
C80.048 (1)0.042 (1)0.044 (1)0.016 (1)0.010 (1)0.009 (1)
C90.054 (1)0.044 (1)0.046 (1)0.016 (1)0.012 (1)0.010 (1)
C100.079 (1)0.050 (1)0.070 (1)0.023 (1)0.032 (1)0.022 (1)
C110.042 (1)0.044 (1)0.046 (1)0.014 (1)0.007 (1)0.008 (1)
C120.047 (1)0.043 (1)0.057 (1)0.015 (1)0.016 (1)0.009 (1)
C130.061 (1)0.054 (1)0.074 (1)0.022 (1)0.005 (1)0.015 (1)
C140.071 (1)0.065 (1)0.115 (2)0.034 (1)0.016 (1)0.035 (1)
C150.085 (1)0.045 (1)0.128 (2)0.027 (1)0.033 (1)0.016 (1)
C160.091 (1)0.048 (1)0.090 (1)0.016 (1)0.025 (1)0.000 (1)
C170.066 (1)0.048 (1)0.064 (1)0.015 (1)0.014 (1)0.006 (1)
C180.048 (1)0.042 (1)0.053 (1)0.015 (1)0.017 (1)0.010 (1)
C190.052 (1)0.067 (1)0.047 (1)0.021 (1)0.008 (1)0.011 (1)
C200.045 (1)0.074 (1)0.060 (1)0.027 (1)0.009 (1)0.012 (1)
C210.046 (1)0.049 (1)0.054 (1)0.014 (1)0.015 (1)0.005 (1)
C220.050 (1)0.046 (1)0.047 (1)0.014 (1)0.010 (1)0.009 (1)
C230.046 (1)0.045 (1)0.057 (1)0.019 (1)0.012 (1)0.014 (1)
C240.082 (1)0.099 (1)0.061 (1)0.028 (1)0.031 (1)0.006 (1)
Geometric parameters (Å, º) top
O1—C71.244 (2)C18—C191.382 (2)
O2—C211.366 (2)C19—C201.374 (2)
O2—C241.416 (2)C20—C211.381 (2)
N1—N21.397 (2)C21—C221.382 (2)
N1—C71.376 (2)C22—C231.385 (2)
N1—C11.414 (2)N3—H3n0.87 (1)
N2—C91.303 (2)C2—H20.9300
N3—C111.329 (2)C3—H30.9300
N3—C181.428 (2)C4—H40.9300
C1—C61.383 (2)C5—H50.9300
C1—C21.383 (2)C6—H60.9300
C2—C31.386 (2)C10—H10a0.9600
C3—C41.376 (3)C10—H10b0.9600
C4—C51.373 (3)C10—H10c0.9600
C5—C61.384 (2)C13—H130.9300
C7—C81.444 (2)C14—H140.9300
C8—C111.391 (2)C15—H150.9300
C8—C91.433 (2)C16—H160.9300
C9—C101.490 (2)C17—H170.9300
C11—C121.484 (2)C19—H190.9300
C12—C131.381 (2)C20—H200.9300
C12—C171.389 (2)C22—H220.9300
C13—C141.382 (2)C23—H230.9300
C14—C151.370 (3)C24—H24a0.9600
C15—C161.367 (3)C24—H24b0.9600
C16—C171.379 (2)C24—H24c0.9600
C18—C231.378 (2)
C21—O2—C24117.4 (1)C18—C23—C22120.8 (1)
N2—N1—C1118.7 (1)C11—N3—H3n113 (1)
N2—N1—C7112.2 (1)C18—N3—H3n121 (1)
C1—N1—C7128.5 (1)C1—C2—H2120.5
C9—N2—N1106.4 (1)C3—C2—H2120.5
C11—N3—C18126.4 (1)C4—C3—H3119.5
C6—C1—C2120.2 (1)C2—C3—H3119.5
C6—C1—N1119.6 (1)C5—C4—H4120.2
C2—C1—N1120.2 (1)C3—C4—H4120.2
C1—C2—C3119.0 (2)C4—C5—H5119.8
C4—C3—C2120.9 (2)C6—C5—H5119.8
C5—C4—C3119.7 (2)C1—C6—H6120.1
C4—C5—C6120.3 (2)C5—C6—H6120.1
C1—C6—C5119.8 (2)C9—C10—H10a109.5
O1—C7—N1126.2 (1)C9—C10—H10b109.5
N1—C7—C8104.4 (1)H10a—C10—H10b109.5
O1—C7—C8129.3 (1)C9—C10—H10c109.5
C7—C8—C9105.2 (1)H10a—C10—H10c109.5
C7—C8—C11122.2 (1)H10b—C10—H10c109.5
C9—C8—C11132.2 (1)C14—C13—H13120.2
N2—C9—C8111.7 (1)C12—C13—H13120.2
N2—C9—C10118.5 (1)C15—C14—H14119.8
C8—C9—C10129.8 (1)C13—C14—H14119.8
N3—C11—C8119.1 (1)C14—C15—H15119.8
N3—C11—C12118.3 (1)C16—C15—H15119.8
C8—C11—C12122.6 (1)C15—C16—H16119.9
C13—C12—C17119.6 (1)C17—C16—H16119.9
C13—C12—C11121.3 (1)C16—C17—H17120.0
C17—C12—C11119.1 (1)C12—C17—H17120.0
C14—C13—C12119.7 (2)C20—C19—H19120.1
C15—C14—C13120.4 (2)C18—C19—H19120.1
C14—C15—C16120.3 (2)C19—C20—H20119.6
C15—C16—C17120.1 (2)C21—C20—H20119.6
C16—C17—C12119.9 (2)C21—C22—H22120.4
C23—C18—C19119.7 (1)C23—C22—H22120.4
C23—C18—N3119.7 (1)C18—C23—H23119.6
C19—C18—N3120.7 (1)C22—C23—H23119.6
C20—C19—C18119.8 (1)O2—C24—H24a109.5
C19—C20—C21120.7 (1)O2—C24—H24b109.5
O2—C21—C20115.7 (1)H24a—C24—H24b109.5
O2—C21—C22124.4 (1)O2—C24—H24c109.5
C20—C21—C22119.8 (1)H24a—C24—H24c109.5
C21—C22—C23119.2 (1)H24b—C24—H24c109.5
C7—N1—N2—C92.6 (2)C9—C8—C11—N3169.8 (1)
C1—N1—N2—C9174.5 (1)C7—C8—C11—N31.9 (2)
C7—N1—C1—C6150.4 (1)C9—C8—C11—C126.5 (2)
N2—N1—C1—C619.9 (2)C7—C8—C11—C12178.2 (1)
C7—N1—C1—C229.4 (2)N3—C11—C12—C13116.0 (2)
N2—N1—C1—C2160.3 (1)C8—C11—C12—C1367.8 (2)
C6—C1—C2—C30.5 (2)N3—C11—C12—C1764.3 (2)
N1—C1—C2—C3179.3 (1)C8—C11—C12—C17112.0 (2)
C1—C2—C3—C40.3 (2)C17—C12—C13—C141.1 (2)
C2—C3—C4—C50.1 (3)C11—C12—C13—C14178.6 (1)
C3—C4—C5—C60.3 (3)C12—C13—C14—C150.3 (3)
C2—C1—C6—C50.3 (2)C13—C14—C15—C161.1 (3)
N1—C1—C6—C5179.5 (1)C14—C15—C16—C170.6 (3)
C4—C5—C6—C10.0 (2)C15—C16—C17—C120.8 (3)
N2—N1—C7—O1174.6 (1)C13—C12—C17—C161.6 (2)
C1—N1—C7—O13.7 (2)C11—C12—C17—C16178.1 (1)
N2—N1—C7—C83.1 (1)C11—N3—C18—C23123.8 (2)
C1—N1—C7—C8174.0 (1)C11—N3—C18—C1957.4 (2)
O1—C7—C8—C111.6 (2)C23—C18—C19—C200.8 (2)
N1—C7—C8—C11176.1 (1)N3—C18—C19—C20179.6 (1)
O1—C7—C8—C9175.2 (1)C18—C19—C20—C210.5 (2)
N1—C7—C8—C92.4 (1)C24—O2—C21—C20168.9 (1)
N1—N2—C9—C80.9 (1)C24—O2—C21—C2212.7 (2)
N1—N2—C9—C10179.3 (1)C19—C20—C21—O2178.9 (1)
C11—C8—C9—N2173.7 (1)C19—C20—C21—C220.4 (2)
C7—C8—C9—N21.0 (1)O2—C21—C22—C23179.4 (1)
C11—C8—C9—C104.4 (2)C20—C21—C22—C231.1 (2)
C7—C8—C9—C10177.1 (1)C19—C18—C23—C220.1 (2)
C18—N3—C11—C8175.4 (1)N3—C18—C23—C22178.9 (1)
C18—N3—C11—C128.2 (2)C21—C22—C23—C180.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3n···O10.87 (1)1.96 (1)2.714 (1)145 (2)
 

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