1-Acetyl-5-(2-methoxy­phenyl)-3-(2-methoxy­styryl)-2-pyrazoline

In the title compound, C₂₁H₂₂N₂O₃, the geometry of the heterodiene (N=C-C=C) indicates the presence of a resonance effect across the C-C bond. The heterodiene prefers the s-trans configuration. The mol­ecules aggregate as double layers parallel to the (101) plane. Consecutive layers, labelled ABAB..., are inversely related to one another.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.139
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

1-Acetyl-5-(2-methoxyphenyl)-3-(2-methoxystyryl)-2-pyrazoline

Crystal data

C21H22N2O3	Z = 2
Mr = 350.41	F(000) = 372
Triclinic, P1	Dx = 1.254 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 8.8485 (11) Å	Cell parameters from 25 reflections
b = 8.9259 (7) Å	θ = 21–46°
c = 12.9652 (15) Å	µ = 0.68 mm^−1
α = 70.074 (9)°	T = 293 K
β = 81.597 (10)°	Plates, yellow
γ = 75.041 (8)°	0.24 × 0.18 × 0.12 mm
V = 928.17 (17) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	3058 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.012
Graphite monochromator	θmax = 69.9°, θmin = 3.6°
ω–2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
Tmin = 0.86, Tmax = 0.92	l = −15→15
3750 measured reflections	2 standard reflections every 1 hour min
3507 independent reflections	intensity decay: <1%

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)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.139	w = 1/[σ^2(Fo^2) + (0.0618P)^2 + 0.3268P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
3507 reflections	Δρmax = 0.30 e Å^−3
236 parameters	Δρmin = −0.23 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: 0.0170 (13)

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 > σ(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	1.17189 (17)	1.35379 (16)	0.54043 (12)	0.0682 (4)
O2	0.79282 (19)	0.46389 (17)	0.97699 (13)	0.0710 (4)
O3	1.25091 (15)	0.83294 (16)	0.51546 (11)	0.0545 (3)
N1	1.05558 (17)	1.17889 (17)	0.67427 (12)	0.0477 (4)
N2	0.96952 (18)	1.13946 (18)	0.77413 (12)	0.0492 (4)
C1	0.9387 (2)	0.9987 (2)	0.79169 (14)	0.0455 (4)
C2	0.9983 (2)	0.9281 (2)	0.69936 (15)	0.0484 (4)
H2A	0.9130	0.9316	0.6587	0.058*
H2B	1.0576	0.8162	0.7265	0.058*
C3	1.10410 (19)	1.0426 (2)	0.62820 (14)	0.0436 (4)
H3	1.0788	1.0806	0.5510	0.052*
C4	1.0949 (2)	1.3265 (2)	0.62799 (16)	0.0526 (4)
C5	1.0405 (3)	1.4474 (2)	0.6901 (2)	0.0719 (6)
H5A	0.9828	1.4003	0.7569	0.108*
H5B	0.9742	1.5444	0.6457	0.108*
H5C	1.1297	1.4749	0.7073	0.108*
C6	0.8491 (2)	0.9276 (2)	0.88997 (15)	0.0499 (4)
H6	0.8128	0.9881	0.9380	0.060*
C7	0.8139 (2)	0.7820 (2)	0.91764 (14)	0.0467 (4)
H7	0.8550	0.7194	0.8713	0.056*
C8	0.7164 (2)	0.7119 (2)	1.01440 (14)	0.0462 (4)
C9	0.6272 (2)	0.8038 (2)	1.07940 (15)	0.0563 (5)
H9	0.6312	0.9129	1.0614	0.068*
C10	0.5334 (3)	0.7378 (3)	1.16930 (17)	0.0676 (6)
H10	0.4745	0.8017	1.2110	0.081*
C11	0.5278 (3)	0.5766 (3)	1.19671 (17)	0.0682 (6)
H11	0.4655	0.5312	1.2578	0.082*
C12	0.6131 (3)	0.4813 (2)	1.13486 (17)	0.0626 (5)
H12	0.6082	0.3722	1.1542	0.075*
C13	0.7063 (2)	0.5481 (2)	1.04370 (15)	0.0513 (4)
C14	1.27648 (19)	0.96288 (19)	0.63860 (13)	0.0412 (4)
C15	1.3654 (2)	0.9879 (2)	0.70772 (16)	0.0535 (4)
H15	1.3192	1.0566	0.7493	0.064*
C16	1.5236 (2)	0.9114 (2)	0.71575 (19)	0.0644 (5)
H16	1.5820	0.9269	0.7638	0.077*
C17	1.5928 (2)	0.8134 (2)	0.65284 (19)	0.0629 (5)
H17	1.6993	0.7651	0.6567	0.075*
C18	1.5065 (2)	0.7854 (2)	0.58373 (16)	0.0524 (4)
H18	1.5543	0.7187	0.5411	0.063*
C19	1.34815 (19)	0.85740 (19)	0.57847 (13)	0.0431 (4)
C20	0.7781 (3)	0.3022 (2)	0.9964 (2)	0.0706 (6)
H20A	0.8453	0.2577	0.9437	0.106*
H20B	0.6714	0.3030	0.9893	0.106*
H20C	0.8078	0.2361	1.0692	0.106*
C21	1.3135 (3)	0.7138 (3)	0.46161 (19)	0.0706 (6)
H21A	1.2344	0.7083	0.4205	0.106*
H21B	1.3475	0.6091	0.5153	0.106*
H21C	1.4011	0.7435	0.4126	0.106*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0705 (9)	0.0500 (8)	0.0725 (9)	−0.0156 (7)	0.0224 (7)	−0.0143 (7)
O2	0.0852 (10)	0.0495 (8)	0.0843 (10)	−0.0225 (7)	0.0203 (8)	−0.0337 (7)
O3	0.0553 (7)	0.0567 (8)	0.0592 (7)	−0.0071 (6)	−0.0039 (6)	−0.0317 (6)
N1	0.0505 (8)	0.0411 (8)	0.0521 (8)	−0.0124 (6)	0.0108 (6)	−0.0198 (6)
N2	0.0546 (8)	0.0446 (8)	0.0503 (8)	−0.0146 (6)	0.0100 (6)	−0.0200 (6)
C1	0.0458 (9)	0.0431 (9)	0.0509 (9)	−0.0124 (7)	0.0016 (7)	−0.0193 (7)
C2	0.0469 (9)	0.0492 (10)	0.0561 (10)	−0.0153 (7)	0.0043 (7)	−0.0252 (8)
C3	0.0444 (9)	0.0433 (9)	0.0453 (9)	−0.0099 (7)	0.0023 (7)	−0.0188 (7)
C4	0.0497 (10)	0.0407 (9)	0.0616 (11)	−0.0090 (7)	0.0059 (8)	−0.0136 (8)
C5	0.0860 (15)	0.0432 (10)	0.0859 (15)	−0.0185 (10)	0.0149 (12)	−0.0251 (10)
C6	0.0575 (10)	0.0478 (10)	0.0482 (9)	−0.0163 (8)	0.0060 (8)	−0.0207 (8)
C7	0.0494 (9)	0.0457 (9)	0.0475 (9)	−0.0125 (7)	0.0001 (7)	−0.0179 (7)
C8	0.0535 (10)	0.0435 (9)	0.0443 (9)	−0.0146 (7)	−0.0031 (7)	−0.0144 (7)
C9	0.0750 (13)	0.0469 (10)	0.0511 (10)	−0.0218 (9)	0.0068 (9)	−0.0192 (8)
C10	0.0900 (15)	0.0622 (12)	0.0553 (11)	−0.0269 (11)	0.0176 (10)	−0.0264 (10)
C11	0.0883 (15)	0.0605 (12)	0.0520 (11)	−0.0289 (11)	0.0143 (10)	−0.0118 (9)
C12	0.0780 (14)	0.0433 (10)	0.0623 (12)	−0.0221 (9)	0.0034 (10)	−0.0085 (9)
C13	0.0583 (10)	0.0432 (9)	0.0532 (10)	−0.0131 (8)	−0.0014 (8)	−0.0159 (8)
C14	0.0438 (9)	0.0368 (8)	0.0423 (8)	−0.0123 (7)	0.0003 (7)	−0.0103 (6)
C15	0.0586 (11)	0.0469 (10)	0.0583 (11)	−0.0125 (8)	−0.0103 (8)	−0.0179 (8)
C16	0.0590 (11)	0.0540 (11)	0.0837 (14)	−0.0155 (9)	−0.0250 (10)	−0.0157 (10)
C17	0.0425 (10)	0.0457 (10)	0.0931 (15)	−0.0106 (8)	−0.0082 (10)	−0.0105 (10)
C18	0.0466 (9)	0.0403 (9)	0.0634 (11)	−0.0096 (7)	0.0081 (8)	−0.0126 (8)
C19	0.0444 (9)	0.0385 (8)	0.0439 (8)	−0.0124 (7)	0.0033 (7)	−0.0100 (7)
C20	0.0829 (15)	0.0463 (11)	0.0886 (16)	−0.0135 (10)	−0.0038 (12)	−0.0302 (11)
C21	0.0820 (15)	0.0675 (13)	0.0727 (14)	−0.0090 (11)	−0.0012 (11)	−0.0425 (11)

Geometric parameters (Å, º)

O1—C4	1.218 (2)	C8—C13	1.404 (2)
O2—C13	1.361 (2)	C9—C10	1.377 (3)
O2—C20	1.416 (2)	C9—H9	0.9300
O3—C19	1.371 (2)	C10—C11	1.372 (3)
O3—C21	1.419 (2)	C10—H10	0.9300
N1—C4	1.361 (2)	C11—C12	1.376 (3)
N1—N2	1.385 (2)	C11—H11	0.9300
N1—C3	1.474 (2)	C12—C13	1.386 (3)
N2—C1	1.292 (2)	C12—H12	0.9300
C1—C6	1.438 (2)	C14—C15	1.381 (2)
C1—C2	1.505 (2)	C14—C19	1.394 (2)
C2—C3	1.539 (2)	C15—C16	1.391 (3)
C2—H2A	0.9700	C15—H15	0.9300
C2—H2B	0.9700	C16—C17	1.368 (3)
C3—C14	1.512 (2)	C16—H16	0.9300
C3—H3	0.9800	C17—C18	1.378 (3)
C4—C5	1.502 (3)	C17—H17	0.9300
C5—H5A	0.9600	C18—C19	1.384 (2)
C5—H5B	0.9600	C18—H18	0.9300
C5—H5C	0.9600	C20—H20A	0.9600
C6—C7	1.332 (2)	C20—H20B	0.9600
C6—H6	0.9300	C20—H20C	0.9600
C7—C8	1.462 (2)	C21—H21A	0.9600
C7—H7	0.9300	C21—H21B	0.9600
C8—C9	1.396 (2)	C21—H21C	0.9600
C13—O2—C20	118.30 (17)	C11—C10—C9	119.3 (2)
C19—O3—C21	117.55 (15)	C11—C10—H10	120.3
C4—N1—N2	122.38 (14)	C9—C10—H10	120.3
C4—N1—C3	124.83 (14)	C10—C11—C12	120.82 (19)
N2—N1—C3	112.74 (13)	C10—C11—H11	119.6
C1—N2—N1	108.16 (14)	C12—C11—H11	119.6
N2—C1—C6	120.16 (15)	C11—C12—C13	119.91 (18)
N2—C1—C2	113.56 (15)	C11—C12—H12	120.0
C6—C1—C2	126.21 (15)	C13—C12—H12	120.0
C1—C2—C3	102.15 (13)	O2—C13—C12	123.99 (17)
C1—C2—H2A	111.3	O2—C13—C8	115.36 (16)
C3—C2—H2A	111.3	C12—C13—C8	120.65 (17)
C1—C2—H2B	111.3	C15—C14—C19	118.48 (16)
C3—C2—H2B	111.3	C15—C14—C3	122.26 (15)
H2A—C2—H2B	109.2	C19—C14—C3	119.24 (14)
N1—C3—C14	112.34 (14)	C14—C15—C16	120.62 (18)
N1—C3—C2	101.09 (13)	C14—C15—H15	119.7
C14—C3—C2	112.46 (14)	C16—C15—H15	119.7
N1—C3—H3	110.2	C17—C16—C15	119.88 (19)
C14—C3—H3	110.2	C17—C16—H16	120.1
C2—C3—H3	110.2	C15—C16—H16	120.1
O1—C4—N1	119.48 (17)	C16—C17—C18	120.68 (18)
O1—C4—C5	123.49 (17)	C16—C17—H17	119.7
N1—C4—C5	117.03 (16)	C18—C17—H17	119.7
C4—C5—H5A	109.5	C17—C18—C19	119.34 (18)
C4—C5—H5B	109.5	C17—C18—H18	120.3
H5A—C5—H5B	109.5	C19—C18—H18	120.3
C4—C5—H5C	109.5	O3—C19—C18	123.94 (16)
H5A—C5—H5C	109.5	O3—C19—C14	115.15 (14)
H5B—C5—H5C	109.5	C18—C19—C14	120.91 (16)
C7—C6—C1	125.21 (16)	O2—C20—H20A	109.5
C7—C6—H6	117.4	O2—C20—H20B	109.5
C1—C6—H6	117.4	H20A—C20—H20B	109.5
C6—C7—C8	125.73 (16)	O2—C20—H20C	109.5
C6—C7—H7	117.1	H20A—C20—H20C	109.5
C8—C7—H7	117.1	H20B—C20—H20C	109.5
C9—C8—C13	117.32 (16)	O3—C21—H21A	109.5
C9—C8—C7	122.27 (16)	O3—C21—H21B	109.5
C13—C8—C7	120.38 (16)	H21A—C21—H21B	109.5
C10—C9—C8	121.95 (18)	O3—C21—H21C	109.5
C10—C9—H9	119.0	H21A—C21—H21C	109.5
C8—C9—H9	119.0	H21B—C21—H21C	109.5
C4—N1—N2—C1	174.28 (17)	C20—O2—C13—C12	5.0 (3)
C3—N1—N2—C1	−8.3 (2)	C20—O2—C13—C8	−174.88 (18)
N1—N2—C1—C6	−179.61 (16)	C11—C12—C13—O2	−179.1 (2)
N1—N2—C1—C2	−2.3 (2)	C11—C12—C13—C8	0.8 (3)
N2—C1—C2—C3	10.9 (2)	C9—C8—C13—O2	178.84 (17)
C6—C1—C2—C3	−171.90 (17)	C7—C8—C13—O2	0.4 (3)
C4—N1—C3—C14	71.6 (2)	C9—C8—C13—C12	−1.1 (3)
N2—N1—C3—C14	−105.71 (16)	C7—C8—C13—C12	−179.51 (18)
C4—N1—C3—C2	−168.27 (17)	N1—C3—C14—C15	15.5 (2)
N2—N1—C3—C2	14.38 (18)	C2—C3—C14—C15	−97.77 (19)
C1—C2—C3—N1	−13.95 (17)	N1—C3—C14—C19	−165.99 (14)
C1—C2—C3—C14	106.06 (16)	C2—C3—C14—C19	80.75 (18)
N2—N1—C4—O1	179.39 (17)	C19—C14—C15—C16	1.0 (3)
C3—N1—C4—O1	2.3 (3)	C3—C14—C15—C16	179.50 (17)
N2—N1—C4—C5	−0.1 (3)	C14—C15—C16—C17	1.5 (3)
C3—N1—C4—C5	−177.17 (18)	C15—C16—C17—C18	−2.0 (3)
N2—C1—C6—C7	−178.25 (18)	C16—C17—C18—C19	−0.1 (3)
C2—C1—C6—C7	4.8 (3)	C21—O3—C19—C18	6.7 (3)
C1—C6—C7—C8	−176.72 (17)	C21—O3—C19—C14	−173.55 (16)
C6—C7—C8—C9	11.0 (3)	C17—C18—C19—O3	−177.64 (16)
C6—C7—C8—C13	−170.60 (18)	C17—C18—C19—C14	2.6 (3)
C13—C8—C9—C10	0.4 (3)	C15—C14—C19—O3	177.21 (15)
C7—C8—C9—C10	178.84 (19)	C3—C14—C19—O3	−1.4 (2)
C8—C9—C10—C11	0.4 (4)	C15—C14—C19—C18	−3.0 (2)
C9—C10—C11—C12	−0.7 (4)	C3—C14—C19—C18	178.37 (15)
C10—C11—C12—C13	0.1 (4)