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In the title compound, C25H21Cl2N3O2, the central benzene ring makes dihedral angles of 65.61 (10), 12.95 (15) and 39.49 (14)°, respectively, with the dichloro­benzene ring, the pyrazolone ring and the terminal phenyl ring. Inter­molecular C—H...O inter­actions help to consolidate the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049324/hb2211sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049324/hb2211Isup2.hkl
Contains datablock I

CCDC reference: 629895

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.048
  • wR factor = 0.128
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for Cl1 - C3 .. 7.47 su
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 40 Perc. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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.

(E)-4-[4-(2,4-Dichlorobenzyloxy)benzylideneamino]-1,5-dimethyl-2-phenyl- 1H-pyrazol-3(2H)-one top
Crystal data top
C25H21Cl2N3O2F(000) = 968
Mr = 466.35Dx = 1.382 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1436 reflections
a = 16.560 (4) Åθ = 2.5–21.2°
b = 6.9670 (19) ŵ = 0.32 mm1
c = 19.771 (5) ÅT = 294 K
β = 100.601 (5)°Block, yellow
V = 2242.1 (10) Å30.28 × 0.24 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
3885 independent reflections
Radiation source: fine-focus sealed tube1552 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.086
φ and ω scansθmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1919
Tmin = 0.897, Tmax = 0.938k = 86
10220 measured reflectionsl = 1923
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0358P)2 + 0.2963P]
where P = (Fo2 + 2Fc2)/3
3885 reflections(Δ/σ)max = 0.002
291 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.45 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
Cl11.47643 (8)0.70006 (18)1.04631 (6)0.0850 (5)
Cl21.27323 (10)1.04494 (19)0.84234 (6)0.0951 (6)
O11.16700 (17)0.5655 (4)0.78486 (12)0.0503 (8)
O20.75089 (18)0.6611 (4)0.46890 (12)0.0564 (8)
N10.8983 (2)0.3795 (4)0.51830 (15)0.0428 (9)
N20.7496 (2)0.2490 (4)0.37197 (15)0.0432 (9)
N30.7122 (2)0.4139 (4)0.39149 (15)0.0434 (9)
C11.2952 (3)0.8439 (6)0.89409 (19)0.0499 (12)
C21.3679 (3)0.8471 (6)0.9418 (2)0.0547 (13)
H21.40280.95250.94490.066*
C31.3872 (3)0.6924 (7)0.98421 (19)0.0481 (12)
C41.3362 (3)0.5358 (6)0.9800 (2)0.0558 (13)
H41.34990.43051.00870.067*
C51.2648 (3)0.5382 (6)0.9323 (2)0.0521 (12)
H51.23010.43240.92940.062*
C61.2425 (3)0.6899 (6)0.88884 (19)0.0435 (11)
C71.1611 (3)0.6902 (6)0.84053 (19)0.0585 (13)
H7A1.11820.64640.86430.070*
H7B1.14760.81910.82360.070*
C81.1010 (3)0.5640 (6)0.73084 (19)0.0411 (11)
C91.1047 (3)0.4292 (5)0.68029 (19)0.0453 (11)
H91.14970.34730.68410.054*
C101.0420 (3)0.4159 (5)0.62434 (18)0.0437 (11)
H101.04440.32320.59090.052*
C110.9757 (3)0.5379 (5)0.61711 (17)0.0374 (10)
C120.9739 (3)0.6723 (6)0.6680 (2)0.0543 (13)
H120.92940.75560.66400.065*
C131.0364 (3)0.6868 (6)0.7249 (2)0.0527 (12)
H131.03420.77920.75850.063*
C140.9067 (3)0.5217 (6)0.55931 (18)0.0465 (12)
H140.86770.61900.55230.056*
C150.8294 (3)0.3679 (5)0.46566 (18)0.0372 (11)
C160.7639 (3)0.5019 (6)0.44685 (19)0.0424 (11)
C170.8182 (3)0.2187 (5)0.42122 (19)0.0400 (11)
C180.8684 (3)0.0424 (5)0.42078 (19)0.0571 (13)
H18A0.91760.05350.45480.086*
H18B0.88270.02660.37620.086*
H18C0.83750.06690.43100.086*
C190.6951 (3)0.0953 (5)0.34053 (19)0.0593 (13)
H19A0.72730.01290.33140.089*
H19B0.66270.14030.29820.089*
H19C0.65940.05770.37140.089*
C200.6540 (3)0.5166 (5)0.3423 (2)0.0391 (11)
C210.6608 (3)0.5185 (6)0.2739 (2)0.0474 (12)
H210.70260.45120.25870.057*
C220.6034 (3)0.6238 (6)0.2281 (2)0.0580 (13)
H220.60610.62430.18150.070*
C230.5433 (3)0.7265 (6)0.2509 (2)0.0644 (14)
H230.50610.79890.22020.077*
C240.5379 (3)0.7225 (6)0.3194 (2)0.0592 (13)
H240.49680.79140.33490.071*
C250.5932 (3)0.6169 (5)0.3653 (2)0.0487 (12)
H250.58930.61370.41160.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0602 (11)0.0942 (10)0.0878 (10)0.0092 (8)0.0200 (7)0.0303 (7)
Cl20.1261 (15)0.0806 (10)0.0760 (9)0.0127 (9)0.0116 (9)0.0287 (7)
O10.044 (2)0.064 (2)0.0397 (17)0.0059 (16)0.0005 (15)0.0212 (14)
O20.063 (2)0.0399 (18)0.0588 (19)0.0075 (16)0.0092 (15)0.0147 (14)
N10.050 (3)0.043 (2)0.034 (2)0.0064 (18)0.0020 (18)0.0021 (15)
N20.051 (3)0.030 (2)0.046 (2)0.0005 (18)0.0037 (19)0.0089 (15)
N30.050 (3)0.032 (2)0.046 (2)0.0055 (19)0.0018 (19)0.0051 (16)
C10.062 (4)0.051 (3)0.037 (3)0.003 (3)0.008 (2)0.0005 (19)
C20.053 (4)0.055 (3)0.058 (3)0.015 (3)0.013 (3)0.009 (2)
C30.032 (3)0.061 (3)0.043 (3)0.006 (3)0.014 (2)0.016 (2)
C40.065 (4)0.045 (3)0.056 (3)0.000 (3)0.005 (3)0.003 (2)
C50.049 (4)0.048 (3)0.055 (3)0.005 (2)0.001 (3)0.009 (2)
C60.047 (4)0.043 (3)0.039 (3)0.001 (2)0.005 (2)0.011 (2)
C70.061 (4)0.066 (3)0.044 (3)0.005 (3)0.002 (3)0.018 (2)
C80.039 (3)0.048 (3)0.033 (2)0.001 (2)0.002 (2)0.004 (2)
C90.041 (3)0.049 (3)0.047 (3)0.001 (2)0.011 (2)0.011 (2)
C100.047 (4)0.045 (3)0.038 (3)0.002 (2)0.006 (2)0.0113 (19)
C110.039 (3)0.038 (2)0.033 (2)0.001 (2)0.000 (2)0.0006 (18)
C120.055 (4)0.051 (3)0.053 (3)0.012 (2)0.001 (3)0.012 (2)
C130.054 (4)0.050 (3)0.048 (3)0.005 (3)0.006 (2)0.021 (2)
C140.048 (3)0.048 (3)0.040 (3)0.001 (2)0.003 (2)0.006 (2)
C150.044 (3)0.031 (2)0.036 (2)0.003 (2)0.004 (2)0.0000 (18)
C160.054 (4)0.032 (3)0.041 (3)0.008 (2)0.007 (2)0.008 (2)
C170.040 (3)0.037 (3)0.040 (3)0.003 (2)0.003 (2)0.0060 (19)
C180.055 (4)0.047 (3)0.065 (3)0.014 (2)0.001 (2)0.004 (2)
C190.066 (4)0.041 (3)0.067 (3)0.007 (3)0.005 (3)0.016 (2)
C200.037 (3)0.033 (2)0.045 (3)0.003 (2)0.001 (2)0.0025 (19)
C210.034 (3)0.054 (3)0.053 (3)0.007 (2)0.004 (2)0.000 (2)
C220.064 (4)0.060 (3)0.046 (3)0.014 (3)0.002 (3)0.008 (2)
C230.062 (4)0.047 (3)0.073 (4)0.003 (3)0.017 (3)0.013 (2)
C240.051 (4)0.041 (3)0.081 (4)0.009 (2)0.001 (3)0.002 (2)
C250.054 (4)0.041 (3)0.049 (3)0.000 (2)0.006 (2)0.000 (2)
Geometric parameters (Å, º) top
Cl1—C31.740 (4)C10—C111.375 (5)
Cl2—C11.733 (4)C10—H100.9300
O1—C81.380 (4)C11—C121.379 (5)
O1—C71.420 (4)C11—C141.463 (5)
O2—C161.225 (4)C12—C131.386 (5)
N1—C141.272 (4)C12—H120.9300
N1—C151.398 (5)C13—H130.9300
N2—C171.370 (5)C14—H140.9300
N2—N31.393 (4)C15—C171.352 (5)
N2—C191.463 (4)C15—C161.428 (5)
N3—C161.401 (4)C17—C181.484 (5)
N3—C201.429 (5)C18—H18A0.9600
C1—C61.376 (5)C18—H18B0.9600
C1—C21.385 (5)C18—H18C0.9600
C2—C31.367 (5)C19—H19A0.9600
C2—H20.9300C19—H19B0.9600
C3—C41.372 (5)C19—H19C0.9600
C4—C51.370 (5)C20—C251.369 (5)
C4—H40.9300C20—C211.378 (5)
C5—C61.370 (5)C21—C221.395 (5)
C5—H50.9300C21—H210.9300
C6—C71.501 (6)C22—C231.369 (6)
C7—H7A0.9700C22—H220.9300
C7—H7B0.9700C23—C241.373 (5)
C8—C131.359 (5)C23—H230.9300
C8—C91.381 (5)C24—C251.377 (5)
C9—C101.374 (5)C24—H240.9300
C9—H90.9300C25—H250.9300
C8—O1—C7116.6 (3)C13—C12—H12119.0
C14—N1—C15119.9 (4)C8—C13—C12118.9 (4)
C17—N2—N3106.4 (3)C8—C13—H13120.5
C17—N2—C19123.7 (3)C12—C13—H13120.5
N3—N2—C19116.8 (3)N1—C14—C11122.5 (4)
N2—N3—C16109.8 (3)N1—C14—H14118.8
N2—N3—C20120.2 (3)C11—C14—H14118.8
C16—N3—C20123.5 (3)C17—C15—N1121.6 (4)
C6—C1—C2121.6 (4)C17—C15—C16109.0 (4)
C6—C1—Cl2121.6 (4)N1—C15—C16129.3 (3)
C2—C1—Cl2116.8 (4)O2—C16—N3123.5 (4)
C3—C2—C1118.8 (4)O2—C16—C15132.4 (4)
C3—C2—H2120.6N3—C16—C15104.1 (3)
C1—C2—H2120.6C15—C17—N2109.9 (4)
C2—C3—C4121.2 (4)C15—C17—C18129.0 (4)
C2—C3—Cl1118.8 (4)N2—C17—C18121.1 (3)
C4—C3—Cl1120.0 (4)C17—C18—H18A109.5
C5—C4—C3118.4 (4)C17—C18—H18B109.5
C5—C4—H4120.8H18A—C18—H18B109.5
C3—C4—H4120.8C17—C18—H18C109.5
C6—C5—C4122.7 (4)H18A—C18—H18C109.5
C6—C5—H5118.6H18B—C18—H18C109.5
C4—C5—H5118.6N2—C19—H19A109.5
C5—C6—C1117.4 (4)N2—C19—H19B109.5
C5—C6—C7120.5 (4)H19A—C19—H19B109.5
C1—C6—C7122.0 (4)N2—C19—H19C109.5
O1—C7—C6108.1 (4)H19A—C19—H19C109.5
O1—C7—H7A110.1H19B—C19—H19C109.5
C6—C7—H7A110.1C25—C20—C21121.3 (4)
O1—C7—H7B110.1C25—C20—N3118.4 (4)
C6—C7—H7B110.1C21—C20—N3120.3 (4)
H7A—C7—H7B108.4C20—C21—C22118.2 (4)
C13—C8—O1124.1 (4)C20—C21—H21120.9
C13—C8—C9120.3 (4)C22—C21—H21120.9
O1—C8—C9115.6 (4)C23—C22—C21120.7 (4)
C10—C9—C8120.1 (4)C23—C22—H22119.6
C10—C9—H9120.0C21—C22—H22119.6
C8—C9—H9120.0C22—C23—C24119.8 (4)
C9—C10—C11120.9 (4)C22—C23—H23120.1
C9—C10—H10119.6C24—C23—H23120.1
C11—C10—H10119.6C23—C24—C25120.4 (4)
C10—C11—C12117.9 (4)C23—C24—H24119.8
C10—C11—C14121.8 (4)C25—C24—H24119.8
C12—C11—C14120.3 (4)C20—C25—C24119.6 (4)
C11—C12—C13121.9 (4)C20—C25—H25120.2
C11—C12—H12119.0C24—C25—H25120.2
C17—N2—N3—C168.9 (4)C10—C11—C14—N110.3 (6)
C19—N2—N3—C16151.8 (3)C12—C11—C14—N1166.7 (4)
C17—N2—N3—C20161.5 (3)C14—N1—C15—C17179.8 (4)
C19—N2—N3—C2055.6 (5)C14—N1—C15—C163.1 (6)
C6—C1—C2—C30.3 (6)N2—N3—C16—O2170.9 (3)
Cl2—C1—C2—C3179.3 (3)C20—N3—C16—O219.3 (6)
C1—C2—C3—C40.2 (6)N2—N3—C16—C157.5 (4)
C1—C2—C3—Cl1177.6 (3)C20—N3—C16—C15159.1 (3)
C2—C3—C4—C50.4 (6)C17—C15—C16—O2174.8 (4)
Cl1—C3—C4—C5177.3 (3)N1—C15—C16—O22.6 (7)
C3—C4—C5—C60.2 (7)C17—C15—C16—N33.4 (4)
C4—C5—C6—C10.3 (6)N1—C15—C16—N3179.2 (4)
C4—C5—C6—C7176.3 (4)N1—C15—C17—N2175.6 (3)
C2—C1—C6—C50.6 (6)C16—C15—C17—N22.0 (5)
Cl2—C1—C6—C5179.5 (3)N1—C15—C17—C184.3 (6)
C2—C1—C6—C7176.0 (4)C16—C15—C17—C18178.1 (4)
Cl2—C1—C6—C72.9 (6)N3—N2—C17—C156.6 (4)
C8—O1—C7—C6172.7 (3)C19—N2—C17—C15146.3 (4)
C5—C6—C7—O176.4 (5)N3—N2—C17—C18173.5 (3)
C1—C6—C7—O1107.2 (4)C19—N2—C17—C1833.8 (6)
C7—O1—C8—C137.1 (6)N2—N3—C20—C25150.9 (4)
C7—O1—C8—C9174.3 (3)C16—N3—C20—C2560.3 (5)
C13—C8—C9—C101.4 (6)N2—N3—C20—C2131.0 (5)
O1—C8—C9—C10179.9 (4)C16—N3—C20—C21117.8 (4)
C8—C9—C10—C111.2 (6)C25—C20—C21—C220.7 (6)
C9—C10—C11—C120.6 (6)N3—C20—C21—C22178.8 (4)
C9—C10—C11—C14177.7 (4)C20—C21—C22—C231.7 (6)
C10—C11—C12—C130.3 (6)C21—C22—C23—C241.6 (7)
C14—C11—C12—C13177.4 (4)C22—C23—C24—C250.6 (6)
O1—C8—C13—C12179.6 (4)C21—C20—C25—C240.3 (6)
C9—C8—C13—C121.0 (6)N3—C20—C25—C24177.8 (4)
C11—C12—C13—C80.5 (7)C23—C24—C25—C200.4 (6)
C15—N1—C14—C11177.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21—H21···O1i0.932.473.323 (5)152
C18—H18C···O2ii0.962.573.526 (5)174
C4—H4···O2iii0.932.603.233 (5)126
Symmetry codes: (i) x+2, y+1, z+1; (ii) x, y1, z; (iii) x+2, y1/2, z+3/2.
 

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