(E)-4-(4-Eth­oxy-3-methoxy­benzyl­ideneamino)-1,5-dimethyl-2-phenyl­pyrazolidin-3-one

In the title compound, C₂₁H₂₃N₃O₃, the substituted vanillin group makes dihedral angles of 48.16 (5) and 4.01 (4)° with the terminal phenyl ring and the pyrazolone ring, respectively. An inter­molecular C—H...O hydrogen bond helps to consolidate the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.040
• wR factor = 0.115
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

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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-Ethoxy-3-methoxybenzylideneamino)-1,5-dimethyl-2-phenylpyrazolidin- 3-one

Crystal data

C21H23N3O3	F(000) = 776
Mr = 365.42	Dx = 1.253 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3033 reflections
a = 16.214 (4) Å	θ = 2.7–25.3°
b = 8.4979 (18) Å	µ = 0.09 mm^−1
c = 14.888 (3) Å	T = 294 K
β = 109.204 (4)°	Block, yellow
V = 1937.1 (7) Å^3	0.22 × 0.20 × 0.18 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3944 independent reflections
Radiation source: fine-focus sealed tube	2373 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 26.4°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→14
Tmin = 0.962, Tmax = 0.983	k = −10→10
10562 measured reflections	l = −18→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.0497P)^2 + 0.3272P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.003
3944 reflections	Δρmax = 0.17 e Å^−3
249 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0083 (10)

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
O1	0.26996 (7)	0.40543 (12)	0.13775 (8)	0.0488 (3)
O2	0.30611 (7)	0.11295 (12)	0.13997 (9)	0.0516 (3)
O3	0.77922 (8)	0.26308 (16)	0.10333 (10)	0.0643 (4)
N1	0.61572 (9)	0.0786 (2)	0.11904 (10)	0.0510 (4)
N2	0.80497 (9)	−0.14220 (17)	0.12679 (10)	0.0477 (4)
N3	0.83278 (9)	0.00824 (17)	0.11010 (10)	0.0491 (4)
C1	0.15317 (13)	0.5720 (2)	0.13647 (15)	0.0647 (6)
H1A	0.1137	0.5312	0.0780	0.097*
H1B	0.1376	0.6786	0.1449	0.097*
H1C	0.1497	0.5089	0.1886	0.097*
C2	0.24456 (12)	0.56752 (19)	0.13335 (13)	0.0508 (5)
H2A	0.2468	0.6151	0.0750	0.061*
H2B	0.2836	0.6250	0.1868	0.061*
C3	0.35002 (11)	0.37209 (19)	0.13092 (11)	0.0426 (4)
C4	0.40966 (12)	0.4808 (2)	0.12123 (13)	0.0550 (5)
H4	0.3969	0.5877	0.1197	0.066*
C5	0.48817 (12)	0.4313 (2)	0.11381 (14)	0.0569 (5)
H5	0.5276	0.5059	0.1068	0.068*
C6	0.50960 (11)	0.2742 (2)	0.11650 (12)	0.0483 (4)
C7	0.44909 (10)	0.1636 (2)	0.12602 (11)	0.0455 (4)
H7	0.4624	0.0569	0.1280	0.055*
C8	0.37040 (10)	0.21095 (18)	0.13253 (11)	0.0403 (4)
C9	0.32241 (12)	−0.05084 (19)	0.14361 (15)	0.0574 (5)
H9A	0.3325	−0.0833	0.0863	0.086*
H9B	0.2728	−0.1061	0.1496	0.086*
H9C	0.3730	−0.0742	0.1974	0.086*
C10	0.59376 (11)	0.2234 (2)	0.11022 (13)	0.0537 (5)
H10	0.6317	0.2976	0.0997	0.064*
C11	0.69634 (10)	0.0285 (2)	0.11570 (12)	0.0464 (4)
C12	0.72015 (11)	−0.1258 (2)	0.12369 (11)	0.0469 (4)
C13	0.76924 (11)	0.1196 (2)	0.10817 (12)	0.0489 (5)
C14	0.66620 (12)	−0.2637 (2)	0.12941 (14)	0.0606 (5)
H14A	0.6520	−0.3227	0.0713	0.091*
H14B	0.6134	−0.2284	0.1388	0.091*
H14C	0.6983	−0.3292	0.1818	0.091*
C15	0.83281 (12)	−0.2726 (2)	0.07940 (14)	0.0596 (5)
H15A	0.8065	−0.3685	0.0907	0.089*
H15B	0.8952	−0.2822	0.1041	0.089*
H15C	0.8149	−0.2526	0.0122	0.089*
C16	0.92318 (10)	0.0383 (2)	0.12880 (12)	0.0470 (4)
C17	0.98658 (12)	−0.0414 (2)	0.19936 (13)	0.0567 (5)
H17	0.9710	−0.1150	0.2372	0.068*
C18	1.07386 (12)	−0.0099 (3)	0.21290 (16)	0.0710 (6)
H18	1.1171	−0.0645	0.2592	0.085*
C19	1.09683 (14)	0.1012 (3)	0.15842 (19)	0.0789 (7)
H19	1.1554	0.1227	0.1683	0.095*
C20	1.03316 (15)	0.1799 (3)	0.08975 (18)	0.0744 (6)
H20	1.0488	0.2556	0.0532	0.089*
C21	0.94644 (12)	0.1490 (2)	0.07387 (14)	0.0596 (5)
H21	0.9036	0.2023	0.0263	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0516 (7)	0.0327 (6)	0.0666 (8)	−0.0001 (5)	0.0256 (6)	−0.0003 (5)
O2	0.0462 (7)	0.0322 (6)	0.0828 (9)	−0.0044 (5)	0.0300 (6)	0.0019 (6)
O3	0.0460 (8)	0.0578 (9)	0.0887 (10)	−0.0064 (6)	0.0216 (7)	0.0086 (7)
N1	0.0338 (8)	0.0706 (11)	0.0474 (9)	−0.0061 (8)	0.0119 (6)	0.0017 (8)
N2	0.0431 (8)	0.0520 (9)	0.0497 (9)	−0.0076 (7)	0.0175 (7)	0.0018 (7)
N3	0.0364 (8)	0.0552 (9)	0.0566 (9)	−0.0071 (7)	0.0165 (7)	0.0066 (7)
C1	0.0719 (14)	0.0508 (12)	0.0763 (14)	0.0138 (10)	0.0310 (11)	0.0060 (10)
C2	0.0667 (12)	0.0323 (9)	0.0548 (11)	0.0036 (9)	0.0216 (9)	0.0020 (8)
C3	0.0436 (10)	0.0391 (10)	0.0450 (10)	−0.0055 (8)	0.0144 (8)	−0.0012 (7)
C4	0.0585 (12)	0.0384 (10)	0.0700 (13)	−0.0087 (9)	0.0235 (10)	0.0017 (9)
C5	0.0504 (11)	0.0515 (12)	0.0699 (13)	−0.0185 (9)	0.0213 (10)	0.0024 (9)
C6	0.0391 (10)	0.0570 (12)	0.0475 (11)	−0.0090 (8)	0.0123 (8)	0.0007 (8)
C7	0.0415 (10)	0.0443 (10)	0.0491 (10)	−0.0025 (8)	0.0129 (8)	0.0026 (8)
C8	0.0397 (9)	0.0365 (9)	0.0452 (10)	−0.0074 (7)	0.0148 (8)	0.0013 (7)
C9	0.0585 (12)	0.0346 (10)	0.0807 (14)	−0.0029 (9)	0.0250 (10)	0.0048 (9)
C10	0.0385 (10)	0.0670 (13)	0.0546 (12)	−0.0134 (9)	0.0139 (9)	0.0014 (9)
C11	0.0343 (9)	0.0627 (12)	0.0411 (10)	−0.0086 (9)	0.0109 (7)	0.0013 (8)
C12	0.0379 (10)	0.0646 (12)	0.0371 (10)	−0.0115 (9)	0.0108 (7)	0.0010 (8)
C13	0.0369 (10)	0.0590 (12)	0.0486 (11)	−0.0047 (9)	0.0113 (8)	0.0045 (9)
C14	0.0525 (11)	0.0699 (13)	0.0608 (12)	−0.0196 (10)	0.0208 (10)	0.0008 (10)
C15	0.0562 (12)	0.0635 (13)	0.0604 (12)	−0.0037 (10)	0.0208 (10)	−0.0040 (10)
C16	0.0338 (9)	0.0590 (11)	0.0503 (11)	−0.0077 (8)	0.0167 (8)	−0.0053 (9)
C17	0.0459 (11)	0.0668 (12)	0.0562 (12)	0.0000 (10)	0.0155 (9)	−0.0045 (10)
C18	0.0411 (11)	0.0798 (15)	0.0846 (16)	0.0067 (11)	0.0105 (11)	−0.0237 (13)
C19	0.0422 (12)	0.0863 (17)	0.118 (2)	−0.0160 (12)	0.0392 (13)	−0.0374 (15)
C20	0.0631 (14)	0.0754 (15)	0.1011 (18)	−0.0189 (12)	0.0495 (14)	−0.0118 (13)
C21	0.0524 (12)	0.0677 (13)	0.0645 (13)	−0.0113 (10)	0.0271 (10)	0.0030 (10)

Geometric parameters (Å, º)

O1—C3	1.365 (2)	C7—C8	1.371 (2)
O1—C2	1.4330 (19)	C7—H7	0.9300
O2—C8	1.3668 (18)	C9—H9A	0.9600
O2—C9	1.414 (2)	C9—H9B	0.9600
O3—C13	1.235 (2)	C9—H9C	0.9600
N1—C10	1.276 (2)	C10—H10	0.9300
N1—C11	1.391 (2)	C11—C12	1.361 (2)
N2—C12	1.368 (2)	C11—C13	1.448 (2)
N2—N3	1.4047 (19)	C12—C14	1.481 (2)
N2—C15	1.462 (2)	C14—H14A	0.9600
N3—C13	1.392 (2)	C14—H14B	0.9600
N3—C16	1.422 (2)	C14—H14C	0.9600
C1—C2	1.498 (3)	C15—H15A	0.9600
C1—H1A	0.9600	C15—H15B	0.9600
C1—H1B	0.9600	C15—H15C	0.9600
C1—H1C	0.9600	C16—C21	1.378 (2)
C2—H2A	0.9700	C16—C17	1.382 (2)
C2—H2B	0.9700	C17—C18	1.388 (3)
C3—C4	1.379 (2)	C17—H17	0.9300
C3—C8	1.407 (2)	C18—C19	1.374 (3)
C4—C5	1.379 (3)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.365 (3)
C5—C6	1.377 (3)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.372 (3)
C6—C7	1.399 (2)	C20—H20	0.9300
C6—C10	1.463 (3)	C21—H21	0.9300
C3—O1—C2	117.53 (13)	H9B—C9—H9C	109.5
C8—O2—C9	117.70 (13)	N1—C10—C6	120.83 (17)
C10—N1—C11	121.67 (16)	N1—C10—H10	119.6
C12—N2—N3	106.19 (14)	C6—C10—H10	119.6
C12—N2—C15	121.84 (15)	C12—C11—N1	122.30 (16)
N3—N2—C15	115.86 (13)	C12—C11—C13	107.85 (15)
C13—N3—N2	110.13 (13)	N1—C11—C13	129.79 (17)
C13—N3—C16	126.13 (15)	C11—C12—N2	110.76 (15)
N2—N3—C16	119.93 (14)	C11—C12—C14	127.67 (17)
C2—C1—H1A	109.5	N2—C12—C14	121.56 (17)
C2—C1—H1B	109.5	O3—C13—N3	124.20 (16)
H1A—C1—H1B	109.5	O3—C13—C11	131.17 (18)
C2—C1—H1C	109.5	N3—C13—C11	104.61 (15)
H1A—C1—H1C	109.5	C12—C14—H14A	109.5
H1B—C1—H1C	109.5	C12—C14—H14B	109.5
O1—C2—C1	107.16 (14)	H14A—C14—H14B	109.5
O1—C2—H2A	110.3	C12—C14—H14C	109.5
C1—C2—H2A	110.3	H14A—C14—H14C	109.5
O1—C2—H2B	110.3	H14B—C14—H14C	109.5
C1—C2—H2B	110.3	N2—C15—H15A	109.5
H2A—C2—H2B	108.5	N2—C15—H15B	109.5
O1—C3—C4	125.86 (15)	H15A—C15—H15B	109.5
O1—C3—C8	115.12 (14)	N2—C15—H15C	109.5
C4—C3—C8	119.00 (16)	H15A—C15—H15C	109.5
C5—C4—C3	120.13 (17)	H15B—C15—H15C	109.5
C5—C4—H4	119.9	C21—C16—C17	120.37 (17)
C3—C4—H4	119.9	C21—C16—N3	118.17 (16)
C6—C5—C4	121.59 (17)	C17—C16—N3	121.46 (16)
C6—C5—H5	119.2	C16—C17—C18	118.94 (19)
C4—C5—H5	119.2	C16—C17—H17	120.5
C5—C6—C7	118.40 (16)	C18—C17—H17	120.5
C5—C6—C10	121.05 (16)	C19—C18—C17	120.5 (2)
C7—C6—C10	120.55 (17)	C19—C18—H18	119.7
C8—C7—C6	120.66 (16)	C17—C18—H18	119.7
C8—C7—H7	119.7	C20—C19—C18	119.6 (2)
C6—C7—H7	119.7	C20—C19—H19	120.2
O2—C8—C7	125.38 (15)	C18—C19—H19	120.2
O2—C8—C3	114.41 (14)	C19—C20—C21	121.0 (2)
C7—C8—C3	120.21 (15)	C19—C20—H20	119.5
O2—C9—H9A	109.5	C21—C20—H20	119.5
O2—C9—H9B	109.5	C20—C21—C16	119.6 (2)
H9A—C9—H9B	109.5	C20—C21—H21	120.2
O2—C9—H9C	109.5	C16—C21—H21	120.2
H9A—C9—H9C	109.5
C12—N2—N3—C13	7.11 (18)	C13—C11—C12—N2	3.05 (19)
C15—N2—N3—C13	145.79 (15)	N1—C11—C12—C14	5.0 (3)
C12—N2—N3—C16	166.45 (14)	C13—C11—C12—C14	−177.38 (16)
C15—N2—N3—C16	−54.9 (2)	N3—N2—C12—C11	−6.19 (18)
C3—O1—C2—C1	176.67 (14)	C15—N2—C12—C11	−141.82 (16)
C2—O1—C3—C4	0.8 (2)	N3—N2—C12—C14	174.21 (15)
C2—O1—C3—C8	−178.01 (14)	C15—N2—C12—C14	38.6 (2)
O1—C3—C4—C5	−179.15 (17)	N2—N3—C13—O3	173.23 (16)
C8—C3—C4—C5	−0.4 (3)	C16—N3—C13—O3	15.5 (3)
C3—C4—C5—C6	−0.5 (3)	N2—N3—C13—C11	−5.21 (17)
C4—C5—C6—C7	0.7 (3)	C16—N3—C13—C11	−162.97 (16)
C4—C5—C6—C10	−178.92 (17)	C12—C11—C13—O3	−176.90 (19)
C5—C6—C7—C8	0.0 (2)	N1—C11—C13—O3	0.4 (3)
C10—C6—C7—C8	179.58 (16)	C12—C11—C13—N3	1.38 (18)
C9—O2—C8—C7	1.6 (2)	N1—C11—C13—N3	178.73 (16)
C9—O2—C8—C3	−178.98 (15)	C13—N3—C16—C21	−54.9 (2)
C6—C7—C8—O2	178.55 (15)	N2—N3—C16—C21	149.32 (16)
C6—C7—C8—C3	−0.8 (2)	C13—N3—C16—C17	125.66 (19)
O1—C3—C8—O2	0.5 (2)	N2—N3—C16—C17	−30.1 (2)
C4—C3—C8—O2	−178.43 (15)	C21—C16—C17—C18	−1.0 (3)
O1—C3—C8—C7	179.92 (14)	N3—C16—C17—C18	178.44 (17)
C4—C3—C8—C7	1.0 (2)	C16—C17—C18—C19	1.4 (3)
C11—N1—C10—C6	−178.34 (15)	C17—C18—C19—C20	−0.7 (3)
C5—C6—C10—N1	175.33 (18)	C18—C19—C20—C21	−0.4 (3)
C7—C6—C10—N1	−4.3 (3)	C19—C20—C21—C16	0.9 (3)
C10—N1—C11—C12	−179.07 (17)	C17—C16—C21—C20	−0.1 (3)
C10—N1—C11—C13	3.9 (3)	N3—C16—C21—C20	−179.59 (18)
N1—C11—C12—N2	−174.54 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15C···O1^i	0.96	2.56	3.310 (2)	135

Symmetry code: (i) −x+1, −y, −z.