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The title compound, C25H22ClN3O2, was prepared by the reaction of 4-amino-1,5-dimethyl-2-phenyl­pyrazol-3-one and 4-(4-chloro­benz­yloxy)benzaldehyde. The substituted benzaldehyde group makes dihedral angles of 58.85 (5), 6.87 (9) and 47.36 (7)° with the chloro­benzyl ring, the pyrazolone ring and the terminal phenyl ring, respectively. Inter­molecular C—H...O hydrogen bonds help to consolidate the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806016801/om2017sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806016801/om2017Isup2.hkl
Contains datablock I

CCDC reference: 610864

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.042
  • wR factor = 0.091
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3
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 0 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL022_ALERT_1_A There is a mismatched ~ on line 83 The title compound, C~25~H~22~Cl~N~3~O~2~, was prepared by the reaction of If you require a ~ then it should be escaped with a \, i.e. \~ Otherwise there must be a matching closing ~, e.g. C~2~H~4~
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

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-(4-Chlorobenzyloxy)benzylideneamino]-1,5-dimethyl-2-phenyl- 1H-pyrazol-3(2H)-one top
Crystal data top
C25H22ClN3O2F(000) = 904
Mr = 431.91Dx = 1.289 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2085 reflections
a = 17.038 (6) Åθ = 2.3–24.2°
b = 6.916 (2) ŵ = 0.20 mm1
c = 19.160 (6) ÅT = 294 K
β = 99.597 (6)°Block, yellow
V = 2226.0 (13) Å30.40 × 0.30 × 0.12 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4572 independent reflections
Radiation source: fine-focus sealed tube2209 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
φ and ω scansθmax = 26.6°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1821
Tmin = 0.920, Tmax = 0.977k = 78
12103 measured reflectionsl = 2323
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.091 w = 1/[σ2(Fo2) + (0.0266P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.003
4572 reflectionsΔρmax = 0.21 e Å3
283 parametersΔρmin = 0.22 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0116 (7)
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
Cl11.47258 (3)0.70901 (10)1.04163 (3)0.0765 (3)
O11.16590 (7)0.5835 (2)0.77754 (7)0.0597 (5)
O20.74676 (8)0.6841 (2)0.47100 (7)0.0588 (4)
N10.88934 (9)0.3938 (3)0.51734 (8)0.0466 (5)
N20.74246 (9)0.2698 (2)0.36860 (8)0.0436 (4)
N30.70736 (9)0.4398 (2)0.39003 (8)0.0434 (4)
C11.30131 (13)0.8729 (4)0.88487 (11)0.0645 (7)
H11.28990.98010.85560.077*
C21.37113 (13)0.8691 (4)0.93457 (12)0.0642 (7)
H21.40620.97320.93870.077*
C31.38739 (11)0.7104 (3)0.97709 (10)0.0481 (6)
C41.33677 (12)0.5545 (3)0.97069 (11)0.0558 (6)
H41.34870.44620.99930.067*
C51.26765 (12)0.5606 (4)0.92110 (11)0.0580 (6)
H51.23330.45530.91650.070*
C61.24901 (12)0.7195 (4)0.87862 (11)0.0503 (6)
C71.17092 (12)0.7343 (4)0.82863 (11)0.0676 (7)
H7A1.12710.72370.85490.081*
H7B1.16720.85890.80500.081*
C81.09953 (11)0.5827 (3)0.72537 (10)0.0479 (6)
C91.09657 (11)0.4347 (3)0.67648 (10)0.0527 (6)
H91.13780.34510.68030.063*
C101.03259 (11)0.4196 (3)0.62199 (10)0.0505 (6)
H101.03070.31840.58980.061*
C110.97077 (11)0.5546 (3)0.61462 (10)0.0454 (6)
C120.97591 (12)0.7023 (3)0.66376 (11)0.0602 (7)
H120.93560.79440.65950.072*
C131.03926 (12)0.7176 (3)0.71917 (10)0.0596 (7)
H131.04110.81770.75180.072*
C140.90153 (11)0.5414 (3)0.55795 (10)0.0516 (6)
H140.86540.64330.55140.062*
C150.85526 (12)0.0533 (3)0.41690 (11)0.0616 (7)
H15A0.90300.06200.45130.092*
H15B0.86890.03570.37070.092*
H15C0.82410.05470.42800.092*
C160.80826 (11)0.2346 (3)0.41805 (10)0.0412 (5)
C170.82201 (11)0.3849 (3)0.46479 (10)0.0396 (5)
C180.75865 (11)0.5231 (3)0.44719 (10)0.0418 (5)
C190.68859 (12)0.1196 (3)0.33516 (11)0.0617 (7)
H19A0.71900.00900.32520.092*
H19B0.65870.16830.29180.092*
H19C0.65270.08280.36650.092*
C200.65264 (11)0.5481 (3)0.34052 (10)0.0388 (5)
C210.66043 (12)0.5580 (3)0.27002 (11)0.0505 (6)
H210.70130.49230.25360.061*
C220.60618 (13)0.6676 (3)0.22393 (12)0.0600 (7)
H220.61060.67410.17630.072*
C230.54629 (13)0.7662 (3)0.24811 (13)0.0627 (7)
H230.51040.83950.21700.075*
C240.53930 (13)0.7566 (3)0.31862 (13)0.0603 (7)
H240.49910.82490.33520.072*
C250.59179 (12)0.6461 (3)0.36472 (11)0.0496 (6)
H250.58620.63760.41210.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0529 (4)0.0848 (5)0.0807 (4)0.0005 (3)0.0207 (3)0.0170 (4)
O10.0403 (8)0.0850 (13)0.0494 (8)0.0067 (8)0.0057 (7)0.0247 (9)
O20.0649 (10)0.0455 (10)0.0591 (9)0.0017 (8)0.0096 (8)0.0167 (8)
N10.0410 (10)0.0576 (14)0.0381 (10)0.0085 (9)0.0028 (9)0.0045 (9)
N20.0450 (10)0.0338 (11)0.0474 (10)0.0015 (9)0.0056 (9)0.0064 (9)
N30.0480 (10)0.0330 (11)0.0447 (10)0.0026 (9)0.0054 (8)0.0079 (9)
C10.0666 (16)0.0664 (19)0.0560 (14)0.0015 (15)0.0027 (13)0.0067 (14)
C20.0579 (16)0.0612 (18)0.0695 (16)0.0214 (13)0.0009 (13)0.0021 (14)
C30.0377 (12)0.0571 (17)0.0473 (13)0.0031 (12)0.0005 (10)0.0118 (12)
C40.0510 (14)0.0572 (17)0.0562 (14)0.0033 (13)0.0002 (12)0.0012 (12)
C50.0483 (14)0.0578 (18)0.0645 (15)0.0118 (12)0.0003 (12)0.0084 (14)
C60.0420 (13)0.0601 (17)0.0462 (13)0.0014 (13)0.0004 (11)0.0147 (13)
C70.0546 (15)0.082 (2)0.0593 (14)0.0040 (13)0.0104 (12)0.0253 (14)
C80.0338 (12)0.0721 (18)0.0357 (11)0.0019 (12)0.0004 (10)0.0076 (12)
C90.0373 (13)0.0720 (18)0.0471 (13)0.0033 (12)0.0021 (11)0.0100 (13)
C100.0488 (14)0.0631 (17)0.0392 (12)0.0054 (13)0.0066 (11)0.0102 (11)
C110.0416 (13)0.0524 (16)0.0400 (12)0.0043 (12)0.0008 (11)0.0012 (12)
C120.0491 (14)0.0619 (17)0.0632 (14)0.0094 (12)0.0093 (12)0.0131 (14)
C130.0460 (14)0.0767 (19)0.0517 (14)0.0078 (13)0.0047 (12)0.0208 (13)
C140.0474 (13)0.0588 (17)0.0447 (13)0.0068 (12)0.0039 (11)0.0035 (13)
C150.0618 (14)0.0488 (16)0.0717 (15)0.0097 (13)0.0036 (12)0.0004 (13)
C160.0396 (12)0.0379 (14)0.0449 (12)0.0010 (11)0.0032 (10)0.0059 (11)
C170.0404 (12)0.0409 (14)0.0356 (11)0.0059 (11)0.0005 (10)0.0059 (10)
C180.0465 (13)0.0357 (14)0.0406 (12)0.0082 (11)0.0006 (10)0.0033 (11)
C190.0654 (15)0.0431 (15)0.0712 (15)0.0102 (12)0.0042 (12)0.0154 (13)
C200.0358 (12)0.0343 (13)0.0424 (13)0.0035 (10)0.0051 (10)0.0047 (11)
C210.0436 (13)0.0572 (16)0.0476 (13)0.0011 (12)0.0021 (11)0.0031 (12)
C220.0612 (15)0.0665 (18)0.0465 (13)0.0062 (14)0.0076 (12)0.0063 (13)
C230.0519 (15)0.0504 (17)0.0763 (18)0.0043 (13)0.0169 (14)0.0068 (14)
C240.0481 (14)0.0473 (16)0.0816 (17)0.0049 (12)0.0005 (13)0.0088 (14)
C250.0464 (13)0.0454 (15)0.0549 (13)0.0016 (12)0.0028 (11)0.0039 (12)
Geometric parameters (Å, º) top
Cl1—C31.7428 (19)C10—C111.397 (3)
O1—C81.379 (2)C10—H100.9300
O1—C71.423 (2)C11—C121.382 (3)
O2—C181.233 (2)C11—C141.467 (2)
N1—C141.279 (2)C12—C131.386 (3)
N1—C171.396 (2)C12—H120.9300
N2—C161.364 (2)C13—H130.9300
N2—N31.411 (2)C14—H140.9300
N2—C191.462 (2)C15—C161.490 (3)
N3—C181.405 (2)C15—H15A0.9600
N3—C201.426 (2)C15—H15B0.9600
C1—C61.378 (3)C15—H15C0.9600
C1—C21.395 (3)C16—C171.367 (3)
C1—H10.9300C17—C181.439 (3)
C2—C31.367 (3)C19—H19A0.9600
C2—H20.9300C19—H19B0.9600
C3—C41.374 (3)C19—H19C0.9600
C4—C51.385 (2)C20—C211.381 (3)
C4—H40.9300C20—C251.382 (3)
C5—C61.373 (3)C21—C221.392 (3)
C5—H50.9300C21—H210.9300
C6—C71.508 (3)C22—C231.371 (3)
C7—H7A0.9700C22—H220.9300
C7—H7B0.9700C23—C241.377 (3)
C8—C131.378 (3)C23—H230.9300
C8—C91.382 (3)C24—C251.379 (3)
C9—C101.382 (2)C24—H240.9300
C9—H90.9300C25—H250.9300
C8—O1—C7116.73 (16)C13—C12—H12119.0
C14—N1—C17120.30 (18)C8—C13—C12119.2 (2)
C16—N2—N3106.62 (15)C8—C13—H13120.4
C16—N2—C19124.11 (17)C12—C13—H13120.4
N3—N2—C19117.03 (15)N1—C14—C11121.9 (2)
C18—N3—N2109.23 (15)N1—C14—H14119.0
C18—N3—C20123.76 (16)C11—C14—H14119.0
N2—N3—C20120.37 (15)C16—C15—H15A109.5
C6—C1—C2120.7 (2)C16—C15—H15B109.5
C6—C1—H1119.6H15A—C15—H15B109.5
C2—C1—H1119.6C16—C15—H15C109.5
C3—C2—C1119.1 (2)H15A—C15—H15C109.5
C3—C2—H2120.4H15B—C15—H15C109.5
C1—C2—H2120.4N2—C16—C17110.52 (18)
C2—C3—C4121.01 (19)N2—C16—C15121.45 (18)
C2—C3—Cl1119.29 (18)C17—C16—C15128.02 (18)
C4—C3—Cl1119.68 (18)C16—C17—N1122.47 (19)
C3—C4—C5119.1 (2)C16—C17—C18108.15 (16)
C3—C4—H4120.4N1—C17—C18129.34 (19)
C5—C4—H4120.4O2—C18—N3122.62 (18)
C6—C5—C4121.2 (2)O2—C18—C17132.54 (18)
C6—C5—H5119.4N3—C18—C17104.80 (17)
C4—C5—H5119.4N2—C19—H19A109.5
C5—C6—C1118.8 (2)N2—C19—H19B109.5
C5—C6—C7121.6 (2)H19A—C19—H19B109.5
C1—C6—C7119.5 (2)N2—C19—H19C109.5
O1—C7—C6109.42 (18)H19A—C19—H19C109.5
O1—C7—H7A109.8H19B—C19—H19C109.5
C6—C7—H7A109.8C21—C20—C25120.25 (19)
O1—C7—H7B109.8C21—C20—N3121.18 (19)
C6—C7—H7B109.8C25—C20—N3118.56 (18)
H7A—C7—H7B108.2C20—C21—C22119.1 (2)
C13—C8—O1124.67 (19)C20—C21—H21120.5
C13—C8—C9120.02 (18)C22—C21—H21120.5
O1—C8—C9115.30 (19)C23—C22—C21120.7 (2)
C10—C9—C8120.2 (2)C23—C22—H22119.7
C10—C9—H9119.9C21—C22—H22119.7
C8—C9—H9119.9C22—C23—C24119.9 (2)
C9—C10—C11120.8 (2)C22—C23—H23120.1
C9—C10—H10119.6C24—C23—H23120.1
C11—C10—H10119.6C23—C24—C25120.1 (2)
C12—C11—C10117.64 (18)C23—C24—H24119.9
C12—C11—C14120.1 (2)C25—C24—H24119.9
C10—C11—C14122.2 (2)C24—C25—C20120.0 (2)
C11—C12—C13122.1 (2)C24—C25—H25120.0
C11—C12—H12119.0C20—C25—H25120.0
C16—N2—N3—C188.5 (2)C10—C11—C14—N18.4 (3)
C19—N2—N3—C18152.56 (16)N3—N2—C16—C177.2 (2)
C16—N2—N3—C20160.99 (16)C19—N2—C16—C17148.05 (18)
C19—N2—N3—C2055.0 (2)N3—N2—C16—C15172.99 (18)
C6—C1—C2—C30.2 (3)C19—N2—C16—C1532.2 (3)
C1—C2—C3—C41.1 (3)N2—C16—C17—N1174.56 (17)
C1—C2—C3—Cl1177.49 (17)C15—C16—C17—N15.2 (3)
C2—C3—C4—C51.1 (3)N2—C16—C17—C183.3 (2)
Cl1—C3—C4—C5177.43 (16)C15—C16—C17—C18177.0 (2)
C3—C4—C5—C60.1 (3)C14—N1—C17—C16176.91 (19)
C4—C5—C6—C11.4 (3)C14—N1—C17—C180.4 (3)
C4—C5—C6—C7175.0 (2)N2—N3—C18—O2171.55 (19)
C2—C1—C6—C51.5 (3)C20—N3—C18—O220.2 (3)
C2—C1—C6—C7175.04 (19)N2—N3—C18—C176.4 (2)
C8—O1—C7—C6176.71 (18)C20—N3—C18—C17157.78 (17)
C5—C6—C7—O162.5 (3)C16—C17—C18—O2175.7 (2)
C1—C6—C7—O1121.1 (2)N1—C17—C18—O22.0 (4)
C7—O1—C8—C130.8 (3)C16—C17—C18—N32.0 (2)
C7—O1—C8—C9179.82 (19)N1—C17—C18—N3179.69 (18)
C13—C8—C9—C101.1 (3)C18—N3—C20—C21115.4 (2)
O1—C8—C9—C10179.82 (18)N2—N3—C20—C2132.9 (3)
C8—C9—C10—C111.1 (3)C18—N3—C20—C2563.6 (3)
C9—C10—C11—C120.2 (3)N2—N3—C20—C25148.04 (18)
C9—C10—C11—C14179.21 (19)C25—C20—C21—C220.1 (3)
C10—C11—C12—C130.6 (3)N3—C20—C21—C22179.12 (18)
C14—C11—C12—C13178.4 (2)C20—C21—C22—C230.7 (3)
O1—C8—C13—C12179.24 (19)C21—C22—C23—C240.2 (3)
C9—C8—C13—C120.3 (3)C22—C23—C24—C250.8 (3)
C11—C12—C13—C80.6 (4)C23—C24—C25—C201.4 (3)
C17—N1—C14—C11178.84 (17)C21—C20—C25—C241.0 (3)
C12—C11—C14—N1170.5 (2)N3—C20—C25—C24178.11 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21—H21···O1i0.932.493.383 (3)161
C4—H4···O2ii0.932.563.220 (3)128
C15—H15C···O2iii0.962.463.413 (3)173
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+2, y1/2, z+3/2; (iii) x, y1, z.
 

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