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

The title compound, C₂₇H₂₆ClN₃O₃, was prepared by reacting 4-amino-1,5-dimethyl-2-phenyl­pyrazol-3-one and 4-(4-chloro­benz­yloxy)-3-ethoxy­benzaldehyde. The central ethyl­vanillin group makes dihedral angles of 63.00 (11), 31.83 (7) and 74.47 (8)° with the chloro­benzene ring, the pyrazolone ring and the terminal phenyl ring, respectively. Packing is stabilized by inter­molecular C—H...O hydrogen bonds that form centrosymmetric dimers.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.055
• wR factor = 0.165
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O2     -   C14     ..       7.71 su

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.51 Ratio
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         C6
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   1 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
   4 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

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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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

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

Crystal data

C27H26ClN3O3	Z = 2
Mr = 475.96	F(000) = 500
Triclinic, P1	Dx = 1.289 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.019 (2) Å	Cell parameters from 1368 reflections
b = 10.355 (2) Å	θ = 2.7–22.2°
c = 12.824 (3) Å	µ = 0.19 mm^−1
α = 77.080 (4)°	T = 294 K
β = 83.710 (4)°	Block, yellow
γ = 71.133 (4)°	0.34 × 0.30 × 0.20 mm
V = 1226.1 (4) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4299 independent reflections
Radiation source: fine-focus sealed tube	2253 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→11
Tmin = 0.928, Tmax = 0.963	k = −7→12
6294 measured reflections	l = −15→14

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.165	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0704P)^2 + 0.1725P] where P = (Fo^2 + 2Fc^2)/3
4299 reflections	(Δ/σ)max = 0.003
310 parameters	Δρmax = 0.41 e Å^−3
18 restraints	Δρmin = −0.27 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	1.23717 (13)	0.40173 (14)	−0.11388 (13)	0.1250 (6)
O1	0.6852 (2)	0.1941 (2)	0.0705 (2)	0.0632 (7)
O2	0.4924 (2)	0.3470 (3)	0.1787 (3)	0.0860 (9)
O3	0.1051 (2)	−0.2193 (2)	0.39294 (18)	0.0592 (7)
N1	0.1251 (3)	0.0816 (3)	0.2981 (2)	0.0459 (7)
N2	−0.2110 (3)	0.0466 (3)	0.3943 (2)	0.0502 (7)
N3	−0.1281 (3)	−0.0929 (3)	0.4246 (2)	0.0488 (7)
C1	0.9389 (4)	0.2313 (4)	−0.1284 (3)	0.0711 (11)
H1	0.8933	0.2152	−0.1812	0.085*
C2	1.0408 (4)	0.2968 (4)	−0.1579 (4)	0.0799 (12)
H2	1.0645	0.3239	−0.2298	0.096*
C3	1.1064 (4)	0.3215 (4)	−0.0803 (4)	0.0698 (11)
C4	1.0729 (4)	0.2805 (4)	0.0257 (3)	0.0731 (11)
H4	1.1181	0.2975	0.0785	0.088*
C5	0.9722 (4)	0.2145 (4)	0.0532 (3)	0.0646 (10)
H5	0.9503	0.1862	0.1253	0.078*
C6	0.9030 (3)	0.1890 (3)	−0.0222 (3)	0.0512 (9)
C7	0.7964 (3)	0.1125 (4)	0.0121 (3)	0.0646 (10)
H7A	0.7603	0.0981	−0.0501	0.077*
H7B	0.8397	0.0223	0.0567	0.077*
C8	0.5825 (3)	0.1372 (3)	0.1179 (3)	0.0477 (8)
C9	0.4754 (3)	0.2219 (3)	0.1760 (3)	0.0527 (9)
C10	0.3667 (3)	0.1754 (3)	0.2245 (3)	0.0514 (9)
H10	0.2956	0.2323	0.2620	0.062*
C11	0.3596 (3)	0.0448 (3)	0.2193 (2)	0.0438 (8)
C12	0.4665 (3)	−0.0376 (3)	0.1647 (3)	0.0488 (8)
H12	0.4650	−0.1261	0.1619	0.059*
C13	0.5768 (3)	0.0083 (3)	0.1135 (3)	0.0512 (9)
H13	0.6474	−0.0488	0.0759	0.061*
C14	0.3819 (5)	0.4473 (4)	0.2154 (5)	0.1054 (16)
H14A	0.3531	0.4106	0.2877	0.126*
H14B	0.3021	0.4732	0.1702	0.126*
C15	0.4249 (4)	0.5706 (4)	0.2146 (4)	0.1011 (16)
H15A	0.5076	0.5435	0.2557	0.152*
H15B	0.3498	0.6373	0.2455	0.152*
H15C	0.4454	0.6114	0.1422	0.152*
C16	0.2401 (3)	−0.0018 (3)	0.2685 (2)	0.0456 (8)
H16	0.2482	−0.0958	0.2786	0.055*
C17	0.0127 (3)	0.0343 (3)	0.3443 (2)	0.0424 (8)
C18	−0.1220 (3)	0.1215 (3)	0.3544 (2)	0.0450 (8)
C19	−0.1730 (4)	0.2756 (3)	0.3275 (3)	0.0662 (10)
H19A	−0.2530	0.3058	0.2832	0.099*
H19B	−0.0990	0.3096	0.2897	0.099*
H19C	−0.2000	0.3114	0.3922	0.099*
C20	−0.3380 (3)	0.0988 (4)	0.4605 (3)	0.0667 (10)
H20A	−0.3122	0.1247	0.5209	0.100*
H20B	−0.3822	0.0273	0.4850	0.100*
H20C	−0.4027	0.1787	0.4187	0.100*
C21	0.0119 (3)	−0.1061 (3)	0.3871 (2)	0.0444 (8)
C22	−0.1927 (3)	−0.2007 (3)	0.4409 (3)	0.0482 (8)
C23	−0.3082 (4)	−0.1838 (4)	0.3843 (3)	0.0633 (10)
H23	−0.3457	−0.1017	0.3352	0.076*
C24	−0.3678 (4)	−0.2900 (5)	0.4010 (4)	0.0799 (12)
H24	−0.4476	−0.2782	0.3647	0.096*
C25	−0.3105 (5)	−0.4123 (5)	0.4705 (4)	0.0829 (14)
H25	−0.3501	−0.4841	0.4801	0.099*
C26	−0.1935 (5)	−0.4293 (4)	0.5268 (4)	0.0795 (13)
H26	−0.1540	−0.5129	0.5736	0.095*
C27	−0.1352 (4)	−0.3214 (4)	0.5132 (3)	0.0636 (10)
H27	−0.0587	−0.3308	0.5524	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0838 (9)	0.1014 (9)	0.1851 (15)	−0.0511 (7)	0.0359 (9)	−0.0053 (9)
O1	0.0453 (13)	0.0583 (14)	0.0878 (19)	−0.0186 (11)	0.0255 (13)	−0.0275 (13)
O2	0.0453 (14)	0.0658 (16)	0.162 (3)	−0.0250 (13)	0.0376 (16)	−0.0610 (17)
O3	0.0436 (13)	0.0482 (14)	0.0761 (18)	−0.0111 (11)	0.0037 (12)	−0.0004 (11)
N1	0.0411 (16)	0.0506 (16)	0.0478 (17)	−0.0182 (13)	−0.0005 (13)	−0.0080 (13)
N2	0.0400 (15)	0.0490 (16)	0.0583 (19)	−0.0107 (13)	0.0056 (14)	−0.0120 (13)
N3	0.0429 (16)	0.0477 (16)	0.0540 (18)	−0.0169 (13)	0.0027 (13)	−0.0046 (13)
C1	0.052 (2)	0.104 (3)	0.056 (3)	−0.020 (2)	0.0018 (19)	−0.022 (2)
C2	0.063 (3)	0.097 (3)	0.062 (3)	−0.020 (2)	0.018 (2)	0.002 (2)
C3	0.047 (2)	0.062 (2)	0.090 (3)	−0.0184 (18)	0.018 (2)	−0.003 (2)
C4	0.060 (2)	0.093 (3)	0.079 (3)	−0.034 (2)	−0.001 (2)	−0.027 (2)
C5	0.059 (2)	0.086 (3)	0.054 (2)	−0.032 (2)	0.0109 (19)	−0.014 (2)
C6	0.0346 (18)	0.062 (2)	0.054 (2)	−0.0116 (16)	0.0092 (16)	−0.0162 (17)
C7	0.045 (2)	0.078 (2)	0.075 (3)	−0.0180 (19)	0.0151 (19)	−0.032 (2)
C8	0.0361 (18)	0.0462 (19)	0.061 (2)	−0.0150 (15)	0.0046 (16)	−0.0109 (16)
C9	0.0416 (19)	0.0450 (19)	0.075 (3)	−0.0156 (16)	0.0105 (18)	−0.0222 (17)
C10	0.0399 (19)	0.055 (2)	0.064 (2)	−0.0173 (16)	0.0103 (16)	−0.0235 (17)
C11	0.0407 (19)	0.0465 (19)	0.046 (2)	−0.0156 (15)	0.0000 (15)	−0.0101 (15)
C12	0.045 (2)	0.0462 (19)	0.058 (2)	−0.0152 (16)	0.0023 (17)	−0.0155 (16)
C13	0.0432 (19)	0.052 (2)	0.057 (2)	−0.0104 (16)	0.0070 (17)	−0.0196 (16)
C14	0.079 (3)	0.075 (3)	0.173 (5)	−0.022 (2)	0.007 (3)	−0.054 (3)
C15	0.074 (3)	0.068 (3)	0.175 (5)	−0.029 (2)	0.007 (3)	−0.048 (3)
C16	0.048 (2)	0.0465 (18)	0.046 (2)	−0.0200 (16)	−0.0036 (16)	−0.0068 (15)
C17	0.0418 (19)	0.0486 (19)	0.0398 (19)	−0.0192 (15)	−0.0005 (15)	−0.0080 (15)
C18	0.0442 (19)	0.0469 (19)	0.046 (2)	−0.0168 (16)	0.0015 (15)	−0.0122 (15)
C19	0.062 (2)	0.053 (2)	0.081 (3)	−0.0149 (18)	0.005 (2)	−0.0159 (19)
C20	0.043 (2)	0.084 (3)	0.067 (3)	−0.0121 (19)	0.0116 (18)	−0.021 (2)
C21	0.0383 (19)	0.053 (2)	0.041 (2)	−0.0151 (16)	0.0014 (15)	−0.0073 (15)
C22	0.0414 (19)	0.055 (2)	0.052 (2)	−0.0221 (16)	0.0107 (16)	−0.0141 (17)
C23	0.059 (2)	0.076 (3)	0.063 (2)	−0.032 (2)	0.0011 (19)	−0.0146 (19)
C24	0.070 (3)	0.091 (3)	0.096 (4)	−0.042 (3)	0.009 (2)	−0.034 (3)
C25	0.069 (3)	0.077 (3)	0.125 (4)	−0.045 (3)	0.036 (3)	−0.053 (3)
C26	0.074 (3)	0.052 (2)	0.101 (3)	−0.022 (2)	0.027 (3)	−0.003 (2)
C27	0.050 (2)	0.061 (2)	0.073 (3)	−0.0179 (18)	0.0054 (19)	−0.001 (2)

Geometric parameters (Å, º)

Cl1—C3	1.735 (4)	C11—C16	1.462 (4)
O1—C8	1.367 (4)	C12—C13	1.385 (4)
O1—C7	1.416 (4)	C12—H12	0.9300
O2—C9	1.369 (4)	C13—H13	0.9300
O2—C14	1.373 (4)	C14—C15	1.471 (5)
O3—C21	1.233 (3)	C14—H14A	0.9700
N1—C16	1.274 (4)	C14—H14B	0.9700
N1—C17	1.393 (4)	C15—H15A	0.9600
N2—C18	1.352 (4)	C15—H15B	0.9600
N2—N3	1.404 (3)	C15—H15C	0.9600
N2—C20	1.468 (4)	C16—H16	0.9300
N3—C21	1.405 (4)	C17—C18	1.370 (4)
N3—C22	1.429 (4)	C17—C21	1.437 (4)
C1—C2	1.376 (5)	C18—C19	1.480 (4)
C1—C6	1.379 (5)	C19—H19A	0.9600
C1—H1	0.9300	C19—H19B	0.9600
C2—C3	1.361 (5)	C19—H19C	0.9600
C2—H2	0.9300	C20—H20A	0.9600
C3—C4	1.369 (5)	C20—H20B	0.9600
C4—C5	1.367 (5)	C20—H20C	0.9600
C4—H4	0.9300	C22—C27	1.374 (4)
C5—C6	1.366 (5)	C22—C23	1.376 (4)
C5—H5	0.9300	C23—C24	1.379 (5)
C6—C7	1.499 (5)	C23—H23	0.9300
C7—H7A	0.9700	C24—C25	1.366 (6)
C7—H7B	0.9700	C24—H24	0.9300
C8—C13	1.368 (4)	C25—C26	1.385 (6)
C8—C9	1.409 (4)	C25—H25	0.9300
C9—C10	1.364 (4)	C26—C27	1.390 (5)
C10—C11	1.394 (4)	C26—H26	0.9300
C10—H10	0.9300	C27—H27	0.9300
C11—C12	1.370 (4)
C8—O1—C7	117.4 (2)	C15—C14—H14A	109.7
C9—O2—C14	119.1 (3)	O2—C14—H14B	109.7
C16—N1—C17	121.2 (3)	C15—C14—H14B	109.7
C18—N2—N3	107.2 (2)	H14A—C14—H14B	108.2
C18—N2—C20	122.7 (3)	C14—C15—H15A	109.5
N3—N2—C20	118.2 (3)	C14—C15—H15B	109.5
N2—N3—C21	109.0 (2)	H15A—C15—H15B	109.5
N2—N3—C22	119.4 (2)	C14—C15—H15C	109.5
C21—N3—C22	125.1 (3)	H15A—C15—H15C	109.5
C2—C1—C6	121.5 (4)	H15B—C15—H15C	109.5
C2—C1—H1	119.2	N1—C16—C11	122.4 (3)
C6—C1—H1	119.2	N1—C16—H16	118.8
C3—C2—C1	119.1 (4)	C11—C16—H16	118.8
C3—C2—H2	120.5	C18—C17—N1	123.1 (3)
C1—C2—H2	120.5	C18—C17—C21	108.1 (3)
C2—C3—C4	120.6 (4)	N1—C17—C21	128.8 (3)
C2—C3—Cl1	120.6 (4)	N2—C18—C17	110.2 (3)
C4—C3—Cl1	118.8 (4)	N2—C18—C19	121.4 (3)
C5—C4—C3	119.3 (4)	C17—C18—C19	128.4 (3)
C5—C4—H4	120.4	C18—C19—H19A	109.5
C3—C4—H4	120.4	C18—C19—H19B	109.5
C6—C5—C4	121.9 (4)	H19A—C19—H19B	109.5
C6—C5—H5	119.1	C18—C19—H19C	109.5
C4—C5—H5	119.1	H19A—C19—H19C	109.5
C5—C6—C1	117.6 (3)	H19B—C19—H19C	109.5
C5—C6—C7	119.8 (3)	N2—C20—H20A	109.5
C1—C6—C7	122.6 (3)	N2—C20—H20B	109.5
O1—C7—C6	107.9 (3)	H20A—C20—H20B	109.5
O1—C7—H7A	110.1	N2—C20—H20C	109.5
C6—C7—H7A	110.1	H20A—C20—H20C	109.5
O1—C7—H7B	110.1	H20B—C20—H20C	109.5
C6—C7—H7B	110.1	O3—C21—N3	123.2 (3)
H7A—C7—H7B	108.4	O3—C21—C17	132.2 (3)
O1—C8—C13	125.8 (3)	N3—C21—C17	104.6 (3)
O1—C8—C9	115.2 (3)	C27—C22—C23	121.3 (3)
C13—C8—C9	119.0 (3)	C27—C22—N3	118.2 (3)
C10—C9—O2	125.6 (3)	C23—C22—N3	120.5 (3)
C10—C9—C8	119.6 (3)	C22—C23—C24	119.2 (4)
O2—C9—C8	114.8 (3)	C22—C23—H23	120.4
C9—C10—C11	121.6 (3)	C24—C23—H23	120.4
C9—C10—H10	119.2	C25—C24—C23	120.6 (4)
C11—C10—H10	119.2	C25—C24—H24	119.7
C12—C11—C10	118.1 (3)	C23—C24—H24	119.7
C12—C11—C16	120.9 (3)	C24—C25—C26	120.0 (4)
C10—C11—C16	121.0 (3)	C24—C25—H25	120.0
C11—C12—C13	121.3 (3)	C26—C25—H25	120.0
C11—C12—H12	119.4	C25—C26—C27	120.0 (4)
C13—C12—H12	119.4	C25—C26—H26	120.0
C8—C13—C12	120.4 (3)	C27—C26—H26	120.0
C8—C13—H13	119.8	C22—C27—C26	118.8 (4)
C12—C13—H13	119.8	C22—C27—H27	120.6
O2—C14—C15	109.9 (4)	C26—C27—H27	120.6
O2—C14—H14A	109.7
C18—N2—N3—C21	−9.2 (3)	C9—O2—C14—C15	178.2 (4)
C20—N2—N3—C21	−153.2 (3)	C17—N1—C16—C11	179.7 (3)
C18—N2—N3—C22	−162.4 (3)	C12—C11—C16—N1	−163.6 (3)
C20—N2—N3—C22	53.6 (4)	C10—C11—C16—N1	15.0 (5)
C6—C1—C2—C3	−0.7 (6)	C16—N1—C17—C18	−164.3 (3)
C1—C2—C3—C4	0.7 (6)	C16—N1—C17—C21	14.7 (5)
C1—C2—C3—Cl1	179.1 (3)	N3—N2—C18—C17	8.1 (3)
C2—C3—C4—C5	−0.1 (6)	C20—N2—C18—C17	150.0 (3)
Cl1—C3—C4—C5	−178.6 (3)	N3—N2—C18—C19	−172.1 (3)
C3—C4—C5—C6	−0.5 (6)	C20—N2—C18—C19	−30.2 (5)
C4—C5—C6—C1	0.5 (5)	N1—C17—C18—N2	175.3 (3)
C4—C5—C6—C7	178.2 (3)	C21—C17—C18—N2	−3.9 (4)
C2—C1—C6—C5	0.1 (5)	N1—C17—C18—C19	−4.5 (5)
C2—C1—C6—C7	−177.6 (3)	C21—C17—C18—C19	176.3 (3)
C8—O1—C7—C6	−174.1 (3)	N2—N3—C21—O3	−172.8 (3)
C5—C6—C7—O1	62.8 (4)	C22—N3—C21—O3	−21.5 (5)
C1—C6—C7—O1	−119.6 (3)	N2—N3—C21—C17	6.7 (3)
C7—O1—C8—C13	−0.4 (5)	C22—N3—C21—C17	158.0 (3)
C7—O1—C8—C9	179.2 (3)	C18—C17—C21—O3	177.6 (3)
C14—O2—C9—C10	−12.7 (6)	N1—C17—C21—O3	−1.6 (6)
C14—O2—C9—C8	167.8 (4)	C18—C17—C21—N3	−1.8 (3)
O1—C8—C9—C10	178.8 (3)	N1—C17—C21—N3	179.0 (3)
C13—C8—C9—C10	−1.5 (5)	N2—N3—C22—C27	−150.8 (3)
O1—C8—C9—O2	−1.7 (4)	C21—N3—C22—C27	60.6 (4)
C13—C8—C9—O2	178.0 (3)	N2—N3—C22—C23	30.1 (4)
O2—C9—C10—C11	−178.6 (3)	C21—N3—C22—C23	−118.5 (3)
C8—C9—C10—C11	0.9 (5)	C27—C22—C23—C24	0.4 (5)
C9—C10—C11—C12	0.8 (5)	N3—C22—C23—C24	179.5 (3)
C9—C10—C11—C16	−177.9 (3)	C22—C23—C24—C25	−2.0 (6)
C10—C11—C12—C13	−1.7 (5)	C23—C24—C25—C26	1.5 (6)
C16—C11—C12—C13	176.9 (3)	C24—C25—C26—C27	0.6 (6)
O1—C8—C13—C12	−179.7 (3)	C23—C22—C27—C26	1.7 (5)
C9—C8—C13—C12	0.6 (5)	N3—C22—C27—C26	−177.5 (3)
C11—C12—C13—C8	1.1 (5)	C25—C26—C27—C22	−2.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···O3^i	0.93	2.60	3.395 (4)	144

Symmetry code: (i) −x, −y−1, −z+1.