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In the title compound, C38H36N6O4, a crystallographic center of symmetry is located at the mid-point of the central C—C bond. The 4-hydroxy­benzaldehyde residue makes dihedral angles of 8.09 (9) and 68.93 (7)°, respectively, with the pyrazolone ring and the terminal phenyl ring. The crystal packing is stabilized by inter­molecular C—H...O hydrogen bonds that link mol­ecules into one-dimensional extended chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037986/at2115sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037986/at2115Isup2.hkl
Contains datablock I

CCDC reference: 623976

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.044
  • wR factor = 0.131
  • Data-to-parameter ratio = 15.4

checkCIF/PLATON results

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Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

4-[(E)-4-(2-{4-[(E)-(1,5-Dimethyl-3-oxo-2-phenyl-2,3- dihydro-1H-pyrazol-4-yl)iminomethyl]phenoxy}ethoxy)benzylideneamino]- 1,5-dimethyl-1-phenyl-1H-dihydropyrazol-3(2H)-one top
Crystal data top
C38H36N6O4F(000) = 676
Mr = 640.73Dx = 1.288 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2144 reflections
a = 13.199 (5) Åθ = 2.2–23.3°
b = 6.802 (3) ŵ = 0.09 mm1
c = 18.841 (7) ÅT = 294 K
β = 102.315 (7)°Block, yellow
V = 1652.6 (11) Å30.38 × 0.26 × 0.20 mm
Z = 2
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3383 independent reflections
Radiation source: fine-focus sealed tube1892 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
φ and ω scansθmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1615
Tmin = 0.951, Tmax = 0.983k = 84
9053 measured reflectionsl = 2322
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0603P)2 + 0.1695P]
where P = (Fo2 + 2Fc2)/3
3383 reflections(Δ/σ)max < 0.001
219 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.18 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.91514 (11)0.1946 (2)0.01277 (9)0.0654 (5)
O20.30821 (11)0.2863 (2)0.10057 (8)0.0572 (4)
N10.51533 (12)0.5312 (2)0.11079 (9)0.0455 (4)
N20.31753 (13)0.7313 (2)0.19154 (9)0.0468 (5)
N30.26376 (12)0.5639 (2)0.15964 (9)0.0440 (4)
C10.94305 (16)0.0018 (3)0.00031 (13)0.0609 (7)
H1A0.90400.04740.04700.073*
H1B0.92910.08880.03730.073*
C20.81793 (15)0.2271 (3)0.02622 (12)0.0483 (5)
C30.80292 (16)0.4106 (3)0.05371 (13)0.0609 (7)
H30.85620.50270.06080.073*
C40.70930 (16)0.4576 (3)0.07060 (13)0.0550 (6)
H40.70030.58110.08950.066*
C50.62822 (15)0.3235 (3)0.05984 (11)0.0414 (5)
C60.64485 (16)0.1416 (3)0.03118 (12)0.0511 (6)
H60.59130.04990.02310.061*
C70.73897 (16)0.0919 (3)0.01417 (11)0.0506 (6)
H70.74830.03100.00510.061*
C80.52845 (15)0.3704 (3)0.07831 (11)0.0449 (5)
H80.47370.28200.06630.054*
C90.42172 (15)0.5723 (3)0.13098 (10)0.0401 (5)
C100.40827 (15)0.7395 (3)0.16863 (11)0.0434 (5)
C110.33060 (15)0.4529 (3)0.12541 (11)0.0427 (5)
C120.47896 (18)0.9100 (3)0.18505 (14)0.0650 (7)
H12A0.44501.02540.16200.097*
H12B0.54060.88540.16710.097*
H12C0.49720.93010.23660.097*
C130.25641 (18)0.9012 (3)0.20473 (14)0.0669 (7)
H13A0.30040.99310.23560.100*
H13B0.20210.85880.22800.100*
H13C0.22650.96330.15930.100*
C140.19317 (15)0.4697 (3)0.19712 (11)0.0424 (5)
C150.21201 (17)0.4641 (3)0.27209 (12)0.0511 (6)
H150.26950.52790.29970.061*
C160.14445 (19)0.3625 (3)0.30571 (14)0.0627 (7)
H160.15630.35870.35610.075*
C170.05970 (19)0.2670 (3)0.26485 (16)0.0644 (7)
H170.01500.19750.28770.077*
C180.04141 (19)0.2747 (3)0.19042 (16)0.0652 (7)
H180.01590.21020.16300.078*
C190.10713 (16)0.3771 (3)0.15589 (12)0.0527 (6)
H190.09370.38390.10550.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0406 (9)0.0658 (10)0.0953 (13)0.0097 (7)0.0273 (9)0.0176 (9)
O20.0596 (10)0.0461 (9)0.0720 (11)0.0055 (7)0.0276 (8)0.0168 (8)
N10.0414 (10)0.0515 (11)0.0466 (11)0.0075 (8)0.0162 (8)0.0004 (8)
N20.0473 (11)0.0389 (10)0.0600 (12)0.0015 (8)0.0245 (9)0.0073 (8)
N30.0429 (10)0.0411 (10)0.0529 (11)0.0015 (8)0.0211 (8)0.0078 (8)
C10.0448 (13)0.0716 (16)0.0695 (17)0.0146 (11)0.0196 (12)0.0179 (12)
C20.0330 (12)0.0608 (14)0.0527 (14)0.0100 (10)0.0126 (10)0.0061 (11)
C30.0405 (13)0.0532 (14)0.0930 (19)0.0015 (11)0.0229 (12)0.0144 (13)
C40.0456 (13)0.0479 (13)0.0747 (17)0.0076 (10)0.0204 (12)0.0107 (11)
C50.0349 (11)0.0506 (12)0.0395 (12)0.0076 (9)0.0095 (9)0.0006 (9)
C60.0357 (12)0.0579 (13)0.0592 (15)0.0001 (10)0.0087 (10)0.0122 (11)
C70.0411 (12)0.0577 (14)0.0530 (14)0.0090 (11)0.0097 (10)0.0169 (11)
C80.0406 (12)0.0513 (13)0.0447 (13)0.0056 (10)0.0132 (10)0.0004 (10)
C90.0388 (11)0.0447 (12)0.0393 (12)0.0055 (9)0.0139 (9)0.0003 (9)
C100.0425 (12)0.0450 (12)0.0445 (13)0.0008 (9)0.0136 (10)0.0016 (10)
C110.0447 (12)0.0430 (12)0.0434 (12)0.0063 (10)0.0160 (10)0.0021 (10)
C120.0622 (16)0.0591 (15)0.0785 (18)0.0125 (12)0.0260 (13)0.0125 (12)
C130.0742 (17)0.0449 (13)0.092 (2)0.0118 (12)0.0399 (15)0.0077 (12)
C140.0385 (12)0.0404 (11)0.0531 (14)0.0052 (9)0.0203 (10)0.0020 (9)
C150.0441 (13)0.0586 (14)0.0523 (14)0.0011 (10)0.0141 (10)0.0005 (11)
C160.0678 (16)0.0665 (16)0.0607 (16)0.0073 (13)0.0292 (13)0.0089 (12)
C170.0594 (16)0.0537 (15)0.089 (2)0.0051 (12)0.0363 (15)0.0059 (14)
C180.0525 (15)0.0620 (15)0.084 (2)0.0118 (12)0.0217 (14)0.0112 (14)
C190.0483 (13)0.0565 (13)0.0544 (15)0.0026 (11)0.0137 (11)0.0078 (11)
Geometric parameters (Å, º) top
O1—C21.378 (2)C7—H70.9300
O1—C11.421 (3)C8—H80.9300
O2—C111.238 (2)C9—C101.372 (3)
N1—C81.283 (2)C9—C111.436 (3)
N1—C91.396 (2)C10—C121.479 (3)
N2—C101.358 (2)C12—H12A0.9600
N2—N31.407 (2)C12—H12B0.9600
N2—C131.460 (2)C12—H12C0.9600
N3—C111.417 (2)C13—H13A0.9600
N3—C141.435 (2)C13—H13B0.9600
C1—C1i1.501 (4)C13—H13C0.9600
C1—H1A0.9700C14—C151.382 (3)
C1—H1B0.9700C14—C191.383 (3)
C2—C71.372 (3)C15—C161.384 (3)
C2—C31.382 (3)C15—H150.9300
C3—C41.378 (3)C16—C171.378 (3)
C3—H30.9300C16—H160.9300
C4—C51.388 (3)C17—C181.372 (3)
C4—H40.9300C17—H170.9300
C5—C61.386 (3)C18—C191.379 (3)
C5—C81.467 (3)C18—H180.9300
C6—C71.389 (3)C19—H190.9300
C6—H60.9300
C2—O1—C1117.93 (17)N1—C9—C11129.99 (18)
C8—N1—C9121.18 (17)N2—C10—C9110.52 (17)
C10—N2—N3107.22 (15)N2—C10—C12121.68 (18)
C10—N2—C13125.33 (17)C9—C10—C12127.79 (19)
N3—N2—C13117.79 (17)O2—C11—N3122.60 (18)
N2—N3—C11108.63 (15)O2—C11—C9132.38 (18)
N2—N3—C14118.21 (15)N3—C11—C9104.97 (17)
C11—N3—C14121.24 (16)C10—C12—H12A109.5
O1—C1—C1i106.2 (2)C10—C12—H12B109.5
O1—C1—H1A110.5H12A—C12—H12B109.5
C1i—C1—H1A110.5C10—C12—H12C109.5
O1—C1—H1B110.5H12A—C12—H12C109.5
C1i—C1—H1B110.5H12B—C12—H12C109.5
H1A—C1—H1B108.7N2—C13—H13A109.5
C7—C2—O1124.52 (19)N2—C13—H13B109.5
C7—C2—C3120.19 (18)H13A—C13—H13B109.5
O1—C2—C3115.29 (18)N2—C13—H13C109.5
C4—C3—C2120.2 (2)H13A—C13—H13C109.5
C4—C3—H3119.9H13B—C13—H13C109.5
C2—C3—H3119.9C15—C14—C19120.6 (2)
C3—C4—C5121.0 (2)C15—C14—N3121.43 (19)
C3—C4—H4119.5C19—C14—N3117.94 (19)
C5—C4—H4119.5C14—C15—C16119.3 (2)
C6—C5—C4117.54 (18)C14—C15—H15120.4
C6—C5—C8120.74 (18)C16—C15—H15120.4
C4—C5—C8121.72 (19)C17—C16—C15120.3 (2)
C5—C6—C7122.04 (19)C17—C16—H16119.8
C5—C6—H6119.0C15—C16—H16119.8
C7—C6—H6119.0C18—C17—C16119.9 (2)
C2—C7—C6118.95 (19)C18—C17—H17120.1
C2—C7—H7120.5C16—C17—H17120.1
C6—C7—H7120.5C17—C18—C19120.7 (2)
N1—C8—C5121.17 (19)C17—C18—H18119.7
N1—C8—H8119.4C19—C18—H18119.7
C5—C8—H8119.4C18—C19—C14119.3 (2)
C10—C9—N1121.76 (18)C18—C19—H19120.4
C10—C9—C11107.93 (16)C14—C19—H19120.4
C10—N2—N3—C118.8 (2)C13—N2—C10—C1228.0 (3)
C13—N2—N3—C11156.78 (18)N1—C9—C10—N2170.52 (17)
C10—N2—N3—C14152.13 (17)C11—C9—C10—N23.6 (2)
C13—N2—N3—C1459.9 (2)N1—C9—C10—C128.9 (3)
C2—O1—C1—C1i170.1 (2)C11—C9—C10—C12177.0 (2)
C1—O1—C2—C713.3 (3)N2—N3—C11—O2170.99 (18)
C1—O1—C2—C3166.6 (2)C14—N3—C11—O229.0 (3)
C7—C2—C3—C41.3 (3)N2—N3—C11—C96.5 (2)
O1—C2—C3—C4178.6 (2)C14—N3—C11—C9148.50 (18)
C2—C3—C4—C50.6 (4)C10—C9—C11—O2175.2 (2)
C3—C4—C5—C60.3 (3)N1—C9—C11—O21.8 (4)
C3—C4—C5—C8179.3 (2)C10—C9—C11—N31.9 (2)
C4—C5—C6—C70.6 (3)N1—C9—C11—N3175.37 (19)
C8—C5—C6—C7179.0 (2)N2—N3—C14—C1533.7 (3)
O1—C2—C7—C6178.9 (2)C11—N3—C14—C15104.8 (2)
C3—C2—C7—C61.1 (3)N2—N3—C14—C19148.77 (18)
C5—C6—C7—C20.1 (3)C11—N3—C14—C1972.7 (2)
C9—N1—C8—C5177.40 (18)C19—C14—C15—C160.8 (3)
C6—C5—C8—N1173.7 (2)N3—C14—C15—C16176.62 (18)
C4—C5—C8—N15.9 (3)C14—C15—C16—C170.4 (3)
C8—N1—C9—C10176.99 (19)C15—C16—C17—C180.8 (4)
C8—N1—C9—C114.3 (3)C16—C17—C18—C190.1 (4)
N3—N2—C10—C97.7 (2)C17—C18—C19—C141.2 (3)
C13—N2—C10—C9152.6 (2)C15—C14—C19—C181.6 (3)
N3—N2—C10—C12172.88 (19)N3—C14—C19—C18175.93 (18)
Symmetry code: (i) x+2, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O2ii0.932.503.332 (3)150
Symmetry code: (ii) x+1, y, z.
 

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