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

In the title compound, C₂₆H₂₃Cl₂N₃O₃, the central vanillin group makes dihedral angles of 51.19 (8), 7.51 (11) and 45.65 (11)° with the dichloro­benzene ring, the pyrazolone ring and the terminal phenyl ring, respectively. 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) = 0.005 Å
• R factor = 0.049
• wR factor = 0.150
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C5
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   3 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
   0 ALERT type 5 Informative message, check

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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)-3-methoxybenzylideneamino]-1,5-dimethyl- 2-phenyl-1H-pyrazol-3(2H)-one

Crystal data

C26H23Cl2N3O3	F(000) = 1032
Mr = 496.37	Dx = 1.352 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2794 reflections
a = 16.952 (3) Å	θ = 2.5–24.9°
b = 7.4311 (12) Å	µ = 0.30 mm^−1
c = 19.699 (3) Å	T = 294 K
β = 100.691 (3)°	Block, yellow
V = 2438.5 (7) Å^3	0.22 × 0.16 × 0.12 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer	4288 independent reflections
Radiation source: fine-focus sealed tube	2509 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 25.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
Tmin = 0.928, Tmax = 0.965	k = −6→8
11826 measured reflections	l = −23→21

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.150	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0664P)^2 + 0.7898P] where P = (Fo^2 + 2Fc^2)/3
4288 reflections	(Δ/σ)max = 0.001
309 parameters	Δρmax = 0.47 e Å^−3
6 restraints	Δρmin = −0.39 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	1.47620 (6)	0.71083 (17)	1.03846 (6)	0.0931 (4)
Cl2	1.28207 (8)	1.10500 (19)	0.85069 (7)	0.1214 (5)
O1	1.16494 (12)	0.6660 (3)	0.77881 (10)	0.0588 (6)
O2	1.15072 (11)	0.3967 (3)	0.69721 (11)	0.0582 (6)
O3	0.73925 (13)	0.7338 (3)	0.46790 (12)	0.0629 (6)
N1	0.88509 (13)	0.4806 (3)	0.52787 (11)	0.0411 (6)
N2	0.70314 (13)	0.4827 (3)	0.39913 (12)	0.0482 (6)
N3	0.74080 (14)	0.3203 (3)	0.38722 (12)	0.0477 (6)
C1	1.26600 (19)	0.6055 (5)	0.91891 (18)	0.0648 (10)
H1	1.2300	0.5099	0.9115	0.078*
C2	1.3363 (2)	0.5848 (5)	0.96589 (18)	0.0650 (10)
H2	1.3482	0.4770	0.9896	0.078*
C3	1.38834 (19)	0.7269 (5)	0.97678 (17)	0.0584 (9)
C4	1.3722 (2)	0.8848 (5)	0.94123 (18)	0.0666 (10)
H4	1.4084	0.9799	0.9489	0.080*
C5	1.3019 (2)	0.9012 (5)	0.89416 (16)	0.0598 (9)
C6	1.24685 (18)	0.7630 (5)	0.88226 (15)	0.0529 (8)
C7	1.1671 (2)	0.7836 (5)	0.83443 (17)	0.0713 (11)
H7A	1.1238	0.7557	0.8588	0.086*
H7B	1.1603	0.9066	0.8179	0.086*
C8	1.09714 (16)	0.6675 (4)	0.72829 (14)	0.0429 (7)
C9	1.03808 (17)	0.7959 (4)	0.72023 (15)	0.0503 (8)
H9	1.0419	0.8922	0.7508	0.060*
C10	0.97261 (18)	0.7823 (4)	0.66653 (15)	0.0516 (8)
H10	0.9328	0.8699	0.6614	0.062*
C11	0.96574 (16)	0.6403 (4)	0.62052 (14)	0.0414 (7)
C12	1.02582 (16)	0.5082 (4)	0.62966 (14)	0.0409 (7)
H12	1.0219	0.4116	0.5992	0.049*
C13	1.09031 (16)	0.5198 (4)	0.68290 (14)	0.0405 (7)
C14	1.1396 (2)	0.2297 (4)	0.66285 (18)	0.0651 (10)
H14A	1.0904	0.1762	0.6703	0.098*
H14B	1.1837	0.1514	0.6806	0.098*
H14C	1.1373	0.2477	0.6143	0.098*
C15	0.89581 (17)	0.6231 (4)	0.56469 (14)	0.0447 (7)
H15	0.8589	0.7168	0.5560	0.054*
C16	0.81860 (16)	0.4580 (4)	0.47596 (13)	0.0393 (7)
C17	0.75307 (17)	0.5782 (4)	0.45165 (14)	0.0458 (7)
C18	0.80698 (16)	0.3048 (4)	0.43674 (14)	0.0416 (7)
C19	0.85738 (19)	0.1391 (4)	0.44441 (17)	0.0582 (9)
H19A	0.8251	0.0375	0.4518	0.087*
H19B	0.9006	0.1526	0.4831	0.087*
H19C	0.8789	0.1207	0.4032	0.087*
C20	0.6922 (2)	0.1706 (5)	0.35374 (18)	0.0670 (10)
H20A	0.7202	0.0593	0.3655	0.100*
H20B	0.6828	0.1867	0.3045	0.100*
H20C	0.6417	0.1677	0.3692	0.100*
C21	0.64576 (17)	0.5651 (4)	0.34651 (16)	0.0491 (8)
C22	0.5838 (2)	0.6589 (5)	0.36636 (19)	0.0658 (10)
H22	0.5790	0.6627	0.4126	0.079*
C23	0.5290 (2)	0.7475 (6)	0.3171 (3)	0.0887 (13)
H23	0.4877	0.8136	0.3302	0.106*
C24	0.5352 (3)	0.7384 (6)	0.2488 (2)	0.0914 (14)
H24	0.4981	0.7978	0.2157	0.110*
C25	0.5962 (2)	0.6417 (6)	0.22933 (19)	0.0797 (12)
H25	0.5994	0.6341	0.1828	0.096*
C26	0.65306 (19)	0.5551 (5)	0.27789 (17)	0.0616 (9)
H26	0.6951	0.4919	0.2647	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0613 (6)	0.1124 (9)	0.0917 (7)	−0.0067 (6)	−0.0220 (5)	−0.0119 (7)
Cl2	0.1206 (10)	0.1061 (10)	0.1322 (10)	−0.0198 (8)	0.0094 (8)	0.0603 (8)
O1	0.0473 (12)	0.0688 (15)	0.0541 (13)	0.0061 (11)	−0.0067 (10)	−0.0282 (12)
O2	0.0468 (12)	0.0511 (13)	0.0705 (14)	0.0082 (10)	−0.0055 (10)	−0.0212 (12)
O3	0.0634 (14)	0.0475 (14)	0.0697 (15)	0.0154 (11)	−0.0085 (11)	−0.0161 (12)
N1	0.0404 (13)	0.0432 (15)	0.0386 (13)	0.0000 (11)	0.0040 (11)	−0.0021 (12)
N2	0.0466 (14)	0.0469 (15)	0.0461 (14)	0.0082 (12)	−0.0048 (12)	−0.0073 (13)
N3	0.0481 (14)	0.0421 (15)	0.0494 (15)	0.0028 (12)	0.0000 (12)	−0.0107 (13)
C1	0.053 (2)	0.054 (2)	0.081 (2)	−0.0135 (17)	−0.0037 (18)	−0.018 (2)
C2	0.060 (2)	0.056 (2)	0.072 (2)	−0.0059 (18)	−0.0028 (18)	−0.0013 (19)
C3	0.0465 (19)	0.072 (3)	0.053 (2)	−0.0078 (18)	0.0000 (15)	−0.0081 (19)
C4	0.057 (2)	0.071 (3)	0.071 (2)	−0.0261 (19)	0.0086 (18)	−0.005 (2)
C5	0.062 (2)	0.067 (2)	0.0512 (19)	−0.0123 (19)	0.0125 (16)	0.0034 (18)
C6	0.0512 (19)	0.061 (2)	0.0428 (17)	−0.0001 (17)	−0.0002 (14)	−0.0184 (17)
C7	0.065 (2)	0.084 (3)	0.058 (2)	0.009 (2)	−0.0066 (17)	−0.036 (2)
C8	0.0397 (16)	0.0465 (18)	0.0410 (16)	−0.0025 (14)	0.0032 (13)	−0.0117 (15)
C9	0.0493 (18)	0.0493 (19)	0.0509 (18)	0.0029 (15)	0.0052 (15)	−0.0194 (16)
C10	0.0492 (18)	0.050 (2)	0.0533 (18)	0.0124 (15)	0.0019 (15)	−0.0112 (16)
C11	0.0393 (16)	0.0441 (17)	0.0406 (16)	−0.0006 (14)	0.0067 (13)	−0.0023 (14)
C12	0.0416 (16)	0.0391 (17)	0.0418 (16)	−0.0062 (14)	0.0075 (13)	−0.0105 (14)
C13	0.0357 (15)	0.0406 (17)	0.0451 (16)	0.0006 (14)	0.0074 (13)	−0.0064 (14)
C14	0.067 (2)	0.045 (2)	0.080 (2)	0.0104 (17)	0.0048 (19)	−0.0147 (19)
C15	0.0444 (17)	0.0455 (18)	0.0413 (16)	0.0058 (14)	0.0006 (13)	−0.0029 (15)
C16	0.0423 (16)	0.0407 (17)	0.0336 (15)	0.0015 (14)	0.0036 (12)	−0.0021 (13)
C17	0.0512 (18)	0.0423 (18)	0.0419 (16)	0.0052 (15)	0.0037 (14)	−0.0041 (15)
C18	0.0406 (16)	0.0420 (17)	0.0411 (16)	0.0024 (14)	0.0049 (13)	−0.0015 (15)
C19	0.0551 (19)	0.048 (2)	0.068 (2)	0.0058 (16)	0.0016 (16)	−0.0086 (17)
C20	0.057 (2)	0.059 (2)	0.077 (2)	−0.0079 (18)	−0.0068 (17)	−0.022 (2)
C21	0.0382 (17)	0.0513 (19)	0.0529 (19)	−0.0057 (15)	−0.0042 (14)	0.0014 (16)
C22	0.057 (2)	0.068 (2)	0.067 (2)	0.0177 (19)	−0.0005 (18)	0.002 (2)
C23	0.064 (2)	0.085 (3)	0.107 (4)	0.022 (2)	−0.010 (2)	0.010 (3)
C24	0.064 (3)	0.093 (3)	0.101 (4)	−0.004 (2)	−0.026 (2)	0.037 (3)
C25	0.060 (2)	0.108 (3)	0.062 (2)	−0.028 (2)	−0.0116 (19)	0.025 (2)
C26	0.0434 (18)	0.081 (3)	0.056 (2)	−0.0122 (18)	−0.0015 (15)	0.0046 (19)

Geometric parameters (Å, º)

Cl1—C3	1.743 (3)	C10—C11	1.382 (4)
Cl2—C5	1.741 (4)	C10—H10	0.9300
O1—C8	1.374 (3)	C11—C12	1.402 (4)
O1—C7	1.397 (3)	C11—C15	1.465 (4)
O2—C13	1.363 (3)	C12—C13	1.370 (4)
O2—C14	1.410 (4)	C12—H12	0.9300
O3—C17	1.234 (3)	C14—H14A	0.9600
N1—C15	1.278 (3)	C14—H14B	0.9600
N1—C16	1.384 (3)	C14—H14C	0.9600
N2—C17	1.402 (4)	C15—H15	0.9300
N2—N3	1.405 (3)	C16—C18	1.370 (4)
N2—C21	1.422 (4)	C16—C17	1.437 (4)
N3—C18	1.348 (3)	C18—C19	1.490 (4)
N3—C20	1.466 (4)	C19—H19A	0.9600
C1—C2	1.376 (4)	C19—H19B	0.9600
C1—C6	1.382 (5)	C19—H19C	0.9600
C1—H1	0.9300	C20—H20A	0.9600
C2—C3	1.367 (5)	C20—H20B	0.9600
C2—H2	0.9300	C20—H20C	0.9600
C3—C4	1.368 (5)	C21—C22	1.376 (4)
C4—C5	1.373 (4)	C21—C26	1.382 (4)
C4—H4	0.9300	C22—C23	1.381 (5)
C5—C6	1.379 (4)	C22—H22	0.9300
C6—C7	1.506 (4)	C23—C24	1.369 (6)
C7—H7A	0.9700	C23—H23	0.9300
C7—H7B	0.9700	C24—C25	1.371 (6)
C8—C9	1.371 (4)	C24—H24	0.9300
C8—C13	1.407 (4)	C25—C26	1.384 (5)
C9—C10	1.388 (4)	C25—H25	0.9300
C9—H9	0.9300	C26—H26	0.9300
C8—O1—C7	117.4 (2)	C12—C13—C8	119.7 (3)
C13—O2—C14	117.6 (2)	O2—C14—H14A	109.5
C15—N1—C16	122.0 (2)	O2—C14—H14B	109.5
C17—N2—N3	109.1 (2)	H14A—C14—H14B	109.5
C17—N2—C21	123.9 (2)	O2—C14—H14C	109.5
N3—N2—C21	121.2 (2)	H14A—C14—H14C	109.5
C18—N3—N2	107.2 (2)	H14B—C14—H14C	109.5
C18—N3—C20	125.7 (3)	N1—C15—C11	120.5 (3)
N2—N3—C20	119.5 (2)	N1—C15—H15	119.7
C2—C1—C6	122.5 (3)	C11—C15—H15	119.7
C2—C1—H1	118.8	C18—C16—N1	122.0 (3)
C6—C1—H1	118.8	C18—C16—C17	107.9 (2)
C3—C2—C1	118.2 (3)	N1—C16—C17	130.1 (3)
C3—C2—H2	120.9	O3—C17—N2	123.2 (3)
C1—C2—H2	120.9	O3—C17—C16	132.0 (3)
C2—C3—C4	121.4 (3)	N2—C17—C16	104.8 (2)
C2—C3—Cl1	120.0 (3)	N3—C18—C16	110.5 (2)
C4—C3—Cl1	118.7 (3)	N3—C18—C19	121.9 (3)
C3—C4—C5	119.2 (3)	C16—C18—C19	127.6 (3)
C3—C4—H4	120.4	C18—C19—H19A	109.5
C5—C4—H4	120.4	C18—C19—H19B	109.5
C4—C5—C6	121.6 (3)	H19A—C19—H19B	109.5
C4—C5—Cl2	118.3 (3)	C18—C19—H19C	109.5
C6—C5—Cl2	120.1 (3)	H19A—C19—H19C	109.5
C5—C6—C1	117.1 (3)	H19B—C19—H19C	109.5
C5—C6—C7	122.1 (3)	N3—C20—H20A	109.5
C1—C6—C7	120.7 (3)	N3—C20—H20B	109.5
O1—C7—C6	108.5 (3)	H20A—C20—H20B	109.5
O1—C7—H7A	110.0	N3—C20—H20C	109.5
C6—C7—H7A	110.0	H20A—C20—H20C	109.5
O1—C7—H7B	110.0	H20B—C20—H20C	109.5
C6—C7—H7B	110.0	C22—C21—C26	121.1 (3)
H7A—C7—H7B	108.4	C22—C21—N2	117.8 (3)
C9—C8—O1	125.8 (3)	C26—C21—N2	121.1 (3)
C9—C8—C13	119.8 (3)	C21—C22—C23	119.4 (4)
O1—C8—C13	114.4 (2)	C21—C22—H22	120.3
C8—C9—C10	120.1 (3)	C23—C22—H22	120.3
C8—C9—H9	120.0	C24—C23—C22	120.2 (4)
C10—C9—H9	120.0	C24—C23—H23	119.9
C11—C10—C9	120.9 (3)	C22—C23—H23	119.9
C11—C10—H10	119.5	C23—C24—C25	120.0 (4)
C9—C10—H10	119.5	C23—C24—H24	120.0
C10—C11—C12	118.6 (3)	C25—C24—H24	120.0
C10—C11—C15	121.1 (3)	C24—C25—C26	121.0 (4)
C12—C11—C15	120.2 (3)	C24—C25—H25	119.5
C13—C12—C11	120.8 (3)	C26—C25—H25	119.5
C13—C12—H12	119.6	C21—C26—C25	118.3 (3)
C11—C12—H12	119.6	C21—C26—H26	120.9
O2—C13—C12	125.3 (3)	C25—C26—H26	120.9
O2—C13—C8	115.0 (2)
C17—N2—N3—C18	7.6 (3)	C9—C8—C13—C12	2.0 (4)
C21—N2—N3—C18	161.8 (3)	O1—C8—C13—C12	−178.9 (3)
C17—N2—N3—C20	158.8 (3)	C16—N1—C15—C11	178.2 (2)
C21—N2—N3—C20	−47.0 (4)	C10—C11—C15—N1	−171.2 (3)
C6—C1—C2—C3	0.7 (5)	C12—C11—C15—N1	6.4 (4)
C1—C2—C3—C4	−1.3 (5)	C15—N1—C16—C18	−179.7 (3)
C1—C2—C3—Cl1	177.2 (3)	C15—N1—C16—C17	1.8 (4)
C2—C3—C4—C5	0.7 (5)	N3—N2—C17—O3	172.1 (3)
Cl1—C3—C4—C5	−177.8 (3)	C21—N2—C17—O3	18.8 (4)
C3—C4—C5—C6	0.5 (5)	N3—N2—C17—C16	−5.9 (3)
C3—C4—C5—Cl2	178.9 (3)	C21—N2—C17—C16	−159.3 (3)
C4—C5—C6—C1	−1.1 (5)	C18—C16—C17—O3	−175.7 (3)
Cl2—C5—C6—C1	−179.4 (2)	N1—C16—C17—O3	3.0 (5)
C4—C5—C6—C7	175.7 (3)	C18—C16—C17—N2	2.2 (3)
Cl2—C5—C6—C7	−2.6 (4)	N1—C16—C17—N2	−179.2 (3)
C2—C1—C6—C5	0.5 (5)	N2—N3—C18—C16	−6.2 (3)
C2—C1—C6—C7	−176.4 (3)	C20—N3—C18—C16	−155.1 (3)
C8—O1—C7—C6	−178.6 (3)	N2—N3—C18—C19	173.7 (3)
C5—C6—C7—O1	115.8 (4)	C20—N3—C18—C19	24.8 (5)
C1—C6—C7—O1	−67.5 (4)	N1—C16—C18—N3	−176.2 (2)
C7—O1—C8—C9	13.3 (5)	C17—C16—C18—N3	2.6 (3)
C7—O1—C8—C13	−165.8 (3)	N1—C16—C18—C19	3.8 (5)
O1—C8—C9—C10	179.6 (3)	C17—C16—C18—C19	−177.4 (3)
C13—C8—C9—C10	−1.4 (5)	C17—N2—C21—C22	−62.6 (4)
C8—C9—C10—C11	0.0 (5)	N3—N2—C21—C22	147.1 (3)
C9—C10—C11—C12	0.9 (4)	C17—N2—C21—C26	115.8 (3)
C9—C10—C11—C15	178.6 (3)	N3—N2—C21—C26	−34.5 (4)
C10—C11—C12—C13	−0.3 (4)	C26—C21—C22—C23	−1.3 (5)
C15—C11—C12—C13	−178.0 (3)	N2—C21—C22—C23	177.1 (3)
C14—O2—C13—C12	−11.9 (4)	C21—C22—C23—C24	1.5 (6)
C14—O2—C13—C8	167.6 (3)	C22—C23—C24—C25	−0.2 (7)
C11—C12—C13—O2	178.3 (3)	C23—C24—C25—C26	−1.3 (6)
C11—C12—C13—C8	−1.1 (4)	C22—C21—C26—C25	−0.2 (5)
C9—C8—C13—O2	−177.5 (3)	N2—C21—C26—C25	−178.5 (3)
O1—C8—C13—O2	1.6 (4)	C24—C25—C26—C21	1.5 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3^i	0.93	2.57	3.281 (4)	133

Symmetry code: (i) −x+2, y−1/2, −z+3/2.