(E)-4-[4-(2,4-Dichloro­benz­yloxy)benzyl­ideneamino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

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.

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

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

Crystal data

C25H21Cl2N3O2	F(000) = 968
Mr = 466.35	Dx = 1.382 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1436 reflections
a = 16.560 (4) Å	θ = 2.5–21.2°
b = 6.9670 (19) Å	µ = 0.32 mm^−1
c = 19.771 (5) Å	T = 294 K
β = 100.601 (5)°	Block, yellow
V = 2242.1 (10) Å^3	0.28 × 0.24 × 0.20 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer	3885 independent reflections
Radiation source: fine-focus sealed tube	1552 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.086
φ and ω scans	θmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
Tmin = 0.897, Tmax = 0.938	k = −8→6
10220 measured reflections	l = −19→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0358P)^2 + 0.2963P] where P = (Fo^2 + 2Fc^2)/3
3885 reflections	(Δ/σ)max = 0.002
291 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.45 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	1.47643 (8)	0.70006 (18)	1.04631 (6)	0.0850 (5)
Cl2	1.27323 (10)	1.04494 (19)	0.84234 (6)	0.0951 (6)
O1	1.16700 (17)	0.5655 (4)	0.78486 (12)	0.0503 (8)
O2	0.75089 (18)	0.6611 (4)	0.46890 (12)	0.0564 (8)
N1	0.8983 (2)	0.3795 (4)	0.51830 (15)	0.0428 (9)
N2	0.7496 (2)	0.2490 (4)	0.37197 (15)	0.0432 (9)
N3	0.7122 (2)	0.4139 (4)	0.39149 (15)	0.0434 (9)
C1	1.2952 (3)	0.8439 (6)	0.89409 (19)	0.0499 (12)
C2	1.3679 (3)	0.8471 (6)	0.9418 (2)	0.0547 (13)
H2	1.4028	0.9525	0.9449	0.066*
C3	1.3872 (3)	0.6924 (7)	0.98421 (19)	0.0481 (12)
C4	1.3362 (3)	0.5358 (6)	0.9800 (2)	0.0558 (13)
H4	1.3499	0.4305	1.0087	0.067*
C5	1.2648 (3)	0.5382 (6)	0.9323 (2)	0.0521 (12)
H5	1.2301	0.4324	0.9294	0.062*
C6	1.2425 (3)	0.6899 (6)	0.88884 (19)	0.0435 (11)
C7	1.1611 (3)	0.6902 (6)	0.84053 (19)	0.0585 (13)
H7A	1.1182	0.6464	0.8643	0.070*
H7B	1.1476	0.8191	0.8236	0.070*
C8	1.1010 (3)	0.5640 (6)	0.73084 (19)	0.0411 (11)
C9	1.1047 (3)	0.4292 (5)	0.68029 (19)	0.0453 (11)
H9	1.1497	0.3473	0.6841	0.054*
C10	1.0420 (3)	0.4159 (5)	0.62434 (18)	0.0437 (11)
H10	1.0444	0.3232	0.5909	0.052*
C11	0.9757 (3)	0.5379 (5)	0.61711 (17)	0.0374 (10)
C12	0.9739 (3)	0.6723 (6)	0.6680 (2)	0.0543 (13)
H12	0.9294	0.7556	0.6640	0.065*
C13	1.0364 (3)	0.6868 (6)	0.7249 (2)	0.0527 (12)
H13	1.0342	0.7792	0.7585	0.063*
C14	0.9067 (3)	0.5217 (6)	0.55931 (18)	0.0465 (12)
H14	0.8677	0.6190	0.5523	0.056*
C15	0.8294 (3)	0.3679 (5)	0.46566 (18)	0.0372 (11)
C16	0.7639 (3)	0.5019 (6)	0.44685 (19)	0.0424 (11)
C17	0.8182 (3)	0.2187 (5)	0.42122 (19)	0.0400 (11)
C18	0.8684 (3)	0.0424 (5)	0.42078 (19)	0.0571 (13)
H18A	0.9176	0.0535	0.4548	0.086*
H18B	0.8827	0.0266	0.3762	0.086*
H18C	0.8375	−0.0669	0.4310	0.086*
C19	0.6951 (3)	0.0953 (5)	0.34053 (19)	0.0593 (13)
H19A	0.7273	−0.0129	0.3314	0.089*
H19B	0.6627	0.1403	0.2982	0.089*
H19C	0.6594	0.0577	0.3714	0.089*
C20	0.6540 (3)	0.5166 (5)	0.3423 (2)	0.0391 (11)
C21	0.6608 (3)	0.5185 (6)	0.2739 (2)	0.0474 (12)
H21	0.7026	0.4512	0.2587	0.057*
C22	0.6034 (3)	0.6238 (6)	0.2281 (2)	0.0580 (13)
H22	0.6061	0.6243	0.1815	0.070*
C23	0.5433 (3)	0.7265 (6)	0.2509 (2)	0.0644 (14)
H23	0.5061	0.7989	0.2202	0.077*
C24	0.5379 (3)	0.7225 (6)	0.3194 (2)	0.0592 (13)
H24	0.4968	0.7914	0.3349	0.071*
C25	0.5932 (3)	0.6169 (5)	0.3653 (2)	0.0487 (12)
H25	0.5893	0.6137	0.4116	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0602 (11)	0.0942 (10)	0.0878 (10)	0.0092 (8)	−0.0200 (7)	−0.0303 (7)
Cl2	0.1261 (15)	0.0806 (10)	0.0760 (9)	−0.0127 (9)	0.0116 (9)	0.0287 (7)
O1	0.044 (2)	0.064 (2)	0.0397 (17)	0.0059 (16)	0.0005 (15)	−0.0212 (14)
O2	0.063 (2)	0.0399 (18)	0.0588 (19)	0.0075 (16)	−0.0092 (15)	−0.0147 (14)
N1	0.050 (3)	0.043 (2)	0.034 (2)	−0.0064 (18)	0.0020 (18)	−0.0021 (15)
N2	0.051 (3)	0.030 (2)	0.046 (2)	−0.0005 (18)	0.0037 (19)	−0.0089 (15)
N3	0.050 (3)	0.032 (2)	0.046 (2)	0.0055 (19)	0.0018 (19)	−0.0051 (16)
C1	0.062 (4)	0.051 (3)	0.037 (3)	−0.003 (3)	0.008 (2)	0.0005 (19)
C2	0.053 (4)	0.055 (3)	0.058 (3)	−0.015 (3)	0.013 (3)	−0.009 (2)
C3	0.032 (3)	0.061 (3)	0.043 (3)	0.006 (3)	−0.014 (2)	−0.016 (2)
C4	0.065 (4)	0.045 (3)	0.056 (3)	0.000 (3)	0.005 (3)	−0.003 (2)
C5	0.049 (4)	0.048 (3)	0.055 (3)	−0.005 (2)	0.001 (3)	−0.009 (2)
C6	0.047 (4)	0.043 (3)	0.039 (3)	−0.001 (2)	0.005 (2)	−0.011 (2)
C7	0.061 (4)	0.066 (3)	0.044 (3)	0.005 (3)	−0.002 (3)	−0.018 (2)
C8	0.039 (3)	0.048 (3)	0.033 (2)	−0.001 (2)	−0.002 (2)	−0.004 (2)
C9	0.041 (3)	0.049 (3)	0.047 (3)	0.001 (2)	0.011 (2)	−0.011 (2)
C10	0.047 (4)	0.045 (3)	0.038 (3)	−0.002 (2)	0.006 (2)	−0.0113 (19)
C11	0.039 (3)	0.038 (2)	0.033 (2)	−0.001 (2)	0.000 (2)	−0.0006 (18)
C12	0.055 (4)	0.051 (3)	0.053 (3)	0.012 (2)	−0.001 (3)	−0.012 (2)
C13	0.054 (4)	0.050 (3)	0.048 (3)	0.005 (3)	−0.006 (2)	−0.021 (2)
C14	0.048 (3)	0.048 (3)	0.040 (3)	0.001 (2)	−0.003 (2)	0.006 (2)
C15	0.044 (3)	0.031 (2)	0.036 (2)	−0.003 (2)	0.004 (2)	0.0000 (18)
C16	0.054 (4)	0.032 (3)	0.041 (3)	−0.008 (2)	0.007 (2)	−0.008 (2)
C17	0.040 (3)	0.037 (3)	0.040 (3)	0.003 (2)	0.003 (2)	0.0060 (19)
C18	0.055 (4)	0.047 (3)	0.065 (3)	0.014 (2)	−0.001 (2)	−0.004 (2)
C19	0.066 (4)	0.041 (3)	0.067 (3)	−0.007 (3)	0.005 (3)	−0.016 (2)
C20	0.037 (3)	0.033 (2)	0.045 (3)	−0.003 (2)	0.001 (2)	−0.0025 (19)
C21	0.034 (3)	0.054 (3)	0.053 (3)	−0.007 (2)	0.004 (2)	0.000 (2)
C22	0.064 (4)	0.060 (3)	0.046 (3)	−0.014 (3)	−0.002 (3)	0.008 (2)
C23	0.062 (4)	0.047 (3)	0.073 (4)	−0.003 (3)	−0.017 (3)	0.013 (2)
C24	0.051 (4)	0.041 (3)	0.081 (4)	0.009 (2)	0.001 (3)	0.002 (2)
C25	0.054 (4)	0.041 (3)	0.049 (3)	0.000 (2)	0.006 (2)	0.000 (2)

Geometric parameters (Å, º)

Cl1—C3	1.740 (4)	C10—C11	1.375 (5)
Cl2—C1	1.733 (4)	C10—H10	0.9300
O1—C8	1.380 (4)	C11—C12	1.379 (5)
O1—C7	1.420 (4)	C11—C14	1.463 (5)
O2—C16	1.225 (4)	C12—C13	1.386 (5)
N1—C14	1.272 (4)	C12—H12	0.9300
N1—C15	1.398 (5)	C13—H13	0.9300
N2—C17	1.370 (5)	C14—H14	0.9300
N2—N3	1.393 (4)	C15—C17	1.352 (5)
N2—C19	1.463 (4)	C15—C16	1.428 (5)
N3—C16	1.401 (4)	C17—C18	1.484 (5)
N3—C20	1.429 (5)	C18—H18A	0.9600
C1—C6	1.376 (5)	C18—H18B	0.9600
C1—C2	1.385 (5)	C18—H18C	0.9600
C2—C3	1.367 (5)	C19—H19A	0.9600
C2—H2	0.9300	C19—H19B	0.9600
C3—C4	1.372 (5)	C19—H19C	0.9600
C4—C5	1.370 (5)	C20—C25	1.369 (5)
C4—H4	0.9300	C20—C21	1.378 (5)
C5—C6	1.370 (5)	C21—C22	1.395 (5)
C5—H5	0.9300	C21—H21	0.9300
C6—C7	1.501 (6)	C22—C23	1.369 (6)
C7—H7A	0.9700	C22—H22	0.9300
C7—H7B	0.9700	C23—C24	1.373 (5)
C8—C13	1.359 (5)	C23—H23	0.9300
C8—C9	1.381 (5)	C24—C25	1.377 (5)
C9—C10	1.374 (5)	C24—H24	0.9300
C9—H9	0.9300	C25—H25	0.9300
C8—O1—C7	116.6 (3)	C13—C12—H12	119.0
C14—N1—C15	119.9 (4)	C8—C13—C12	118.9 (4)
C17—N2—N3	106.4 (3)	C8—C13—H13	120.5
C17—N2—C19	123.7 (3)	C12—C13—H13	120.5
N3—N2—C19	116.8 (3)	N1—C14—C11	122.5 (4)
N2—N3—C16	109.8 (3)	N1—C14—H14	118.8
N2—N3—C20	120.2 (3)	C11—C14—H14	118.8
C16—N3—C20	123.5 (3)	C17—C15—N1	121.6 (4)
C6—C1—C2	121.6 (4)	C17—C15—C16	109.0 (4)
C6—C1—Cl2	121.6 (4)	N1—C15—C16	129.3 (3)
C2—C1—Cl2	116.8 (4)	O2—C16—N3	123.5 (4)
C3—C2—C1	118.8 (4)	O2—C16—C15	132.4 (4)
C3—C2—H2	120.6	N3—C16—C15	104.1 (3)
C1—C2—H2	120.6	C15—C17—N2	109.9 (4)
C2—C3—C4	121.2 (4)	C15—C17—C18	129.0 (4)
C2—C3—Cl1	118.8 (4)	N2—C17—C18	121.1 (3)
C4—C3—Cl1	120.0 (4)	C17—C18—H18A	109.5
C5—C4—C3	118.4 (4)	C17—C18—H18B	109.5
C5—C4—H4	120.8	H18A—C18—H18B	109.5
C3—C4—H4	120.8	C17—C18—H18C	109.5
C6—C5—C4	122.7 (4)	H18A—C18—H18C	109.5
C6—C5—H5	118.6	H18B—C18—H18C	109.5
C4—C5—H5	118.6	N2—C19—H19A	109.5
C5—C6—C1	117.4 (4)	N2—C19—H19B	109.5
C5—C6—C7	120.5 (4)	H19A—C19—H19B	109.5
C1—C6—C7	122.0 (4)	N2—C19—H19C	109.5
O1—C7—C6	108.1 (4)	H19A—C19—H19C	109.5
O1—C7—H7A	110.1	H19B—C19—H19C	109.5
C6—C7—H7A	110.1	C25—C20—C21	121.3 (4)
O1—C7—H7B	110.1	C25—C20—N3	118.4 (4)
C6—C7—H7B	110.1	C21—C20—N3	120.3 (4)
H7A—C7—H7B	108.4	C20—C21—C22	118.2 (4)
C13—C8—O1	124.1 (4)	C20—C21—H21	120.9
C13—C8—C9	120.3 (4)	C22—C21—H21	120.9
O1—C8—C9	115.6 (4)	C23—C22—C21	120.7 (4)
C10—C9—C8	120.1 (4)	C23—C22—H22	119.6
C10—C9—H9	120.0	C21—C22—H22	119.6
C8—C9—H9	120.0	C22—C23—C24	119.8 (4)
C9—C10—C11	120.9 (4)	C22—C23—H23	120.1
C9—C10—H10	119.6	C24—C23—H23	120.1
C11—C10—H10	119.6	C23—C24—C25	120.4 (4)
C10—C11—C12	117.9 (4)	C23—C24—H24	119.8
C10—C11—C14	121.8 (4)	C25—C24—H24	119.8
C12—C11—C14	120.3 (4)	C20—C25—C24	119.6 (4)
C11—C12—C13	121.9 (4)	C20—C25—H25	120.2
C11—C12—H12	119.0	C24—C25—H25	120.2
C17—N2—N3—C16	8.9 (4)	C10—C11—C14—N1	10.3 (6)
C19—N2—N3—C16	151.8 (3)	C12—C11—C14—N1	−166.7 (4)
C17—N2—N3—C20	161.5 (3)	C14—N1—C15—C17	−179.8 (4)
C19—N2—N3—C20	−55.6 (5)	C14—N1—C15—C16	3.1 (6)
C6—C1—C2—C3	0.3 (6)	N2—N3—C16—O2	170.9 (3)
Cl2—C1—C2—C3	179.3 (3)	C20—N3—C16—O2	19.3 (6)
C1—C2—C3—C4	0.2 (6)	N2—N3—C16—C15	−7.5 (4)
C1—C2—C3—Cl1	−177.6 (3)	C20—N3—C16—C15	−159.1 (3)
C2—C3—C4—C5	−0.4 (6)	C17—C15—C16—O2	−174.8 (4)
Cl1—C3—C4—C5	177.3 (3)	N1—C15—C16—O2	2.6 (7)
C3—C4—C5—C6	0.2 (7)	C17—C15—C16—N3	3.4 (4)
C4—C5—C6—C1	0.3 (6)	N1—C15—C16—N3	−179.2 (4)
C4—C5—C6—C7	−176.3 (4)	N1—C15—C17—N2	−175.6 (3)
C2—C1—C6—C5	−0.6 (6)	C16—C15—C17—N2	2.0 (5)
Cl2—C1—C6—C5	−179.5 (3)	N1—C15—C17—C18	4.3 (6)
C2—C1—C6—C7	176.0 (4)	C16—C15—C17—C18	−178.1 (4)
Cl2—C1—C6—C7	−2.9 (6)	N3—N2—C17—C15	−6.6 (4)
C8—O1—C7—C6	−172.7 (3)	C19—N2—C17—C15	−146.3 (4)
C5—C6—C7—O1	−76.4 (5)	N3—N2—C17—C18	173.5 (3)
C1—C6—C7—O1	107.2 (4)	C19—N2—C17—C18	33.8 (6)
C7—O1—C8—C13	7.1 (6)	N2—N3—C20—C25	150.9 (4)
C7—O1—C8—C9	−174.3 (3)	C16—N3—C20—C25	−60.3 (5)
C13—C8—C9—C10	−1.4 (6)	N2—N3—C20—C21	−31.0 (5)
O1—C8—C9—C10	179.9 (4)	C16—N3—C20—C21	117.8 (4)
C8—C9—C10—C11	1.2 (6)	C25—C20—C21—C22	−0.7 (6)
C9—C10—C11—C12	−0.6 (6)	N3—C20—C21—C22	−178.8 (4)
C9—C10—C11—C14	−177.7 (4)	C20—C21—C22—C23	1.7 (6)
C10—C11—C12—C13	0.3 (6)	C21—C22—C23—C24	−1.6 (7)
C14—C11—C12—C13	177.4 (4)	C22—C23—C24—C25	0.6 (6)
O1—C8—C13—C12	179.6 (4)	C21—C20—C25—C24	−0.3 (6)
C9—C8—C13—C12	1.0 (6)	N3—C20—C25—C24	177.8 (4)
C11—C12—C13—C8	−0.5 (7)	C23—C24—C25—C20	0.4 (6)
C15—N1—C14—C11	177.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O1^i	0.93	2.47	3.323 (5)	152
C18—H18C···O2^ii	0.96	2.57	3.526 (5)	174
C4—H4···O2^iii	0.93	2.60	3.233 (5)	126

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, y−1, z; (iii) −x+2, y−1/2, −z+3/2.