3-[4-(Dimethyl­amino)phen­yl]-2-(4-methoxy­phen­yl)acrylonitrile

A new dipolarophile for the construction of the bioactive title compound, C₁₈H₁₈N₂O, was synthesized by base-catalysed reaction of benzaldehyde with (4-methoxy­phen­yl)acetonitrile. The olefinic bond connecting the (4-methoxy­phen­yl)acetonitrile and the dimethyl­amino­phenyl groups has a Z geometry.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.146
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95

Author Response: ...We have collected data on kappa IP diffractometer and processed using Denzo; and the DENZO image processing package is known to have problems with certain strong reflections. They are often excluded from the data set leading to a lower value for the above parameter.

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C9     -   C10     ..       5.60 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C9     -   C10    ...       1.44 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 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
   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


checkCIF publication errors

Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 256
              ^1^H NMR (CDCl~3~): \d 2.74--2.84 [s, 6H, N-(CH~3~)2], 3.67 (s, 3H, O~CH~3~),
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON.

3-[4-(Dimethylamino)phenyl]-2-(4-methoxyphenyl)acrylonitrile

Crystal data

C18H18N2O	F(000) = 592
Mr = 278.34	Dx = 1.238 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3743 reflections
a = 11.736 (9) Å	θ = 2.1–25.0°
b = 7.646 (8) Å	µ = 0.08 mm^−1
c = 19.932 (12) Å	T = 295 K
β = 123.379 (5)°	Block, colourless
V = 1494 (2) Å^3	0.30 × 0.25 × 0.25 mm
Z = 4

Data collection

MacScience DIPLabo 32001 diffractometer	2080 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Graphite monochromator	θmax = 25.0°, θmin = 2.1°
Detector resolution: 10.0 pixels mm^-1	h = −13→13
ω scans	k = −7→9
3743 measured reflections	l = −23→23
2514 independent reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.146	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0771P)^2 + 0.2878P] where P = (Fo^2 + 2Fc^2)/3
2514 reflections	(Δ/σ)max < 0.001
194 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

Experimental. ¹H NMR (CDCl₃): δ 2.74–2.84 [s, 6H, N-(CH₃)2], 3.67 (s, 3H, OCH₃), 6.68–6.74 (dd, 2H, Ar—H), 6.78–6.94 (dd, 2H, Ar—H), 6.95–7.03 (dd, 2H, Ar—H), 7.42–7.56 (dd, 2H, Ar—H), 7.33 (s, 1H, CH═C—Ar).

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2, conventional R-factors R are based on F, with F set to zero for negative F^2. The observed criterion of F^2 > σ(F^2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2 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
O7	−0.00932 (13)	0.05309 (19)	0.07640 (7)	0.0709 (5)
N11	0.4614 (2)	0.2569 (3)	0.48227 (10)	0.0866 (7)
N19	0.39223 (14)	−0.04193 (19)	0.78632 (8)	0.0568 (5)
C1	0.06170 (17)	−0.0477 (2)	0.27638 (10)	0.0567 (6)
C2	0.18226 (16)	0.0457 (2)	0.32572 (10)	0.0490 (5)
C3	0.23468 (17)	0.1351 (2)	0.28736 (10)	0.0559 (6)
C4	0.17012 (17)	0.1342 (2)	0.20500 (10)	0.0573 (6)
C5	0.04933 (17)	0.0426 (2)	0.15745 (10)	0.0528 (5)
C6	−0.00367 (17)	−0.0494 (2)	0.19379 (10)	0.0570 (6)
C8	−0.1360 (2)	−0.0334 (4)	0.02493 (12)	0.0859 (9)
C9	0.25090 (16)	0.0533 (2)	0.41424 (10)	0.0516 (5)
C10	0.36958 (19)	0.1638 (3)	0.45424 (10)	0.0611 (6)
C12	0.20808 (18)	−0.0272 (2)	0.45694 (11)	0.0578 (6)
C13	0.26186 (18)	−0.0292 (2)	0.54215 (10)	0.0548 (5)
C14	0.18134 (18)	−0.1027 (2)	0.56713 (11)	0.0599 (6)
C15	0.22244 (17)	−0.1082 (2)	0.64631 (10)	0.0583 (6)
C16	0.34950 (16)	−0.0399 (2)	0.70716 (10)	0.0500 (5)
C17	0.43190 (18)	0.0303 (2)	0.68261 (11)	0.0583 (6)
C18	0.38904 (18)	0.0350 (2)	0.60342 (11)	0.0602 (6)
C20	0.31140 (19)	−0.1262 (3)	0.81134 (11)	0.0688 (7)
C21	0.52760 (18)	0.0169 (3)	0.84844 (11)	0.0643 (6)
H1	0.02430	−0.11060	0.29980	0.0680*
H3	0.31570	0.19730	0.31830	0.0670*
H4	0.20770	0.19510	0.18130	0.0690*
H6	−0.08390	−0.11300	0.16250	0.0680*
H8A	−0.12490	−0.15650	0.03620	0.1290*
H8B	−0.16580	−0.01440	−0.03000	0.1290*
H8C	−0.20280	0.01240	0.03380	0.1290*
H12	0.12950	−0.09380	0.42590	0.0690*
H14	0.09680	−0.14960	0.52850	0.0720*
H15	0.16540	−0.15780	0.65990	0.0700*
H17	0.51750	0.07450	0.72120	0.0700*
H18	0.44670	0.08280	0.58980	0.0720*
H20A	0.22240	−0.07380	0.78400	0.1030*
H20B	0.35520	−0.11240	0.86830	0.1030*
H20C	0.30290	−0.24850	0.79840	0.1030*
H21A	0.59440	−0.05650	0.84890	0.0960*
H21B	0.53820	0.01060	0.89970	0.0960*
H21C	0.54000	0.13550	0.83790	0.0960*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O7	0.0675 (8)	0.0896 (10)	0.0524 (7)	−0.0199 (7)	0.0310 (6)	−0.0032 (6)
N11	0.0958 (13)	0.0954 (14)	0.0647 (10)	−0.0395 (11)	0.0416 (9)	−0.0104 (9)
N19	0.0558 (8)	0.0623 (9)	0.0536 (8)	−0.0027 (6)	0.0310 (7)	0.0013 (6)
C1	0.0573 (10)	0.0566 (10)	0.0601 (10)	−0.0075 (7)	0.0347 (9)	0.0023 (8)
C2	0.0520 (9)	0.0418 (8)	0.0557 (9)	0.0023 (6)	0.0312 (8)	0.0004 (7)
C3	0.0534 (9)	0.0542 (10)	0.0605 (10)	−0.0069 (7)	0.0315 (8)	−0.0026 (7)
C4	0.0583 (10)	0.0591 (10)	0.0609 (10)	−0.0089 (8)	0.0368 (8)	0.0000 (8)
C5	0.0557 (9)	0.0524 (10)	0.0535 (9)	−0.0001 (7)	0.0320 (8)	−0.0012 (7)
C6	0.0548 (10)	0.0565 (10)	0.0594 (10)	−0.0092 (7)	0.0312 (8)	−0.0035 (7)
C8	0.0760 (14)	0.1124 (19)	0.0582 (11)	−0.0323 (12)	0.0299 (11)	−0.0104 (11)
C9	0.0542 (9)	0.0451 (9)	0.0559 (9)	0.0005 (7)	0.0305 (8)	−0.0011 (7)
C10	0.0714 (11)	0.0606 (11)	0.0547 (9)	−0.0087 (9)	0.0369 (9)	−0.0027 (8)
C12	0.0584 (10)	0.0564 (10)	0.0567 (10)	−0.0042 (7)	0.0304 (8)	−0.0008 (8)
C13	0.0579 (10)	0.0514 (9)	0.0545 (9)	−0.0011 (7)	0.0306 (8)	0.0014 (7)
C14	0.0554 (10)	0.0646 (11)	0.0576 (10)	−0.0089 (8)	0.0297 (8)	−0.0017 (8)
C15	0.0550 (10)	0.0622 (11)	0.0615 (10)	−0.0071 (7)	0.0344 (8)	0.0017 (8)
C16	0.0542 (9)	0.0432 (9)	0.0544 (9)	0.0025 (6)	0.0311 (8)	0.0018 (7)
C17	0.0546 (10)	0.0614 (11)	0.0572 (10)	−0.0090 (8)	0.0296 (8)	−0.0002 (8)
C18	0.0610 (11)	0.0659 (11)	0.0582 (10)	−0.0097 (8)	0.0356 (9)	0.0013 (8)
C20	0.0674 (11)	0.0820 (14)	0.0661 (11)	0.0004 (9)	0.0424 (10)	0.0085 (9)
C21	0.0635 (11)	0.0698 (12)	0.0567 (10)	−0.0057 (8)	0.0312 (9)	−0.0052 (8)

Geometric parameters (Å, º)

O7—C5	1.366 (3)	C16—C17	1.408 (3)
O7—C8	1.422 (3)	C17—C18	1.368 (3)
N11—C10	1.148 (3)	C1—H1	0.9313
N19—C16	1.368 (3)	C3—H3	0.9303
N19—C20	1.444 (3)	C4—H4	0.9294
N19—C21	1.447 (3)	C6—H6	0.9305
C1—C2	1.396 (3)	C8—H8A	0.9598
C1—C6	1.382 (3)	C8—H8B	0.9596
C2—C3	1.396 (3)	C8—H8C	0.9597
C2—C9	1.484 (3)	C12—H12	0.9299
C3—C4	1.379 (3)	C14—H14	0.9302
C4—C5	1.386 (3)	C15—H15	0.9300
C5—C6	1.379 (3)	C17—H17	0.9300
C9—C10	1.438 (3)	C18—H18	0.9313
C9—C12	1.351 (3)	C20—H20A	0.9603
C12—C13	1.450 (3)	C20—H20B	0.9603
C13—C14	1.405 (3)	C20—H20C	0.9605
C13—C18	1.398 (3)	C21—H21A	0.9601
C14—C15	1.374 (3)	C21—H21B	0.9601
C15—C16	1.406 (3)	C21—H21C	0.9598
O7···C8^i	3.286 (5)	H3···C10	2.4335
O7···H14^ii	2.8690	H4···C16^iv	3.0069
O7···H8B^i	2.6941	H6···C8	2.5334
N11···C3	3.415 (4)	H6···H8A	2.3123
N11···C18	3.419 (5)	H6···H8C	2.3470
N11···H3	2.7683	H6···C2^xii	2.9148
N11···H18	2.6081	H6···C9^xii	3.0647
N11···H20B^iii	2.7292	H8A···C6	2.7647
N11···H21B^iv	2.8833	H8A···H6	2.3123
C3···N11	3.415 (4)	H8A···C12^xii	3.0253
C8···O7^i	3.286 (5)	H8B···C21^v	3.0467
C8···C21^v	3.582 (5)	H8B···H21A^v	2.5250
C10···C18	3.019 (4)	H8B···O7^i	2.6941
C10···C10^vi	3.582 (5)	H8C···C6	2.7665
C18···N11	3.419 (5)	H8C···H6	2.3470
C18···C10	3.019 (4)	H12···C1	2.6514
C21···C8^vii	3.582 (5)	H12···H1	2.1080
C1···H20A^viii	3.0022	H12···H14	2.3184
C1···H20C^ix	3.0441	H14···H12	2.3184
C1···H12	2.6514	H14···O7^xii	2.8690
C2···H6^ii	2.9148	H15···C20	2.5327
C2···H20C^ix	2.8833	H15···H20A	2.2711
C3···H20C^ix	3.0386	H15···H20C	2.4091
C4···H1^ii	2.9635	H17···C21	2.5118
C5···H1^ii	3.0519	H17···H21A	2.4018
C6···H8A	2.7647	H17···H21C	2.2410
C6···H8C	2.7665	H18···N11	2.6081
C6···H20A^viii	2.9872	H18···C9	2.9544
C8···H6	2.5334	H18···C10	2.4109
C9···H6^ii	3.0647	H20A···C15	2.7573
C9···H18	2.9544	H20A···H15	2.2711
C10···H18	2.4109	H20A···C1^viii	3.0022
C10···H3	2.4335	H20A···C6^viii	2.9872
C12···H1	2.7268	H20B···H21B	2.0999
C12···H8A^ii	3.0253	H20B···N11^xi	2.7292
C15···H20C	2.8429	H20C···C15	2.8429
C15···H20A	2.7573	H20C···H15	2.4091
C16···H4^x	3.0069	H20C···C1^xiii	3.0441
C17···H21C^xi	3.0881	H20C···C2^xiii	2.8833
C17···H21C	2.7416	H20C···C3^xiii	3.0386
C17···H21A	2.8474	H21A···C17	2.8474
C20···H15	2.5327	H21A···H8B^vii	2.5250
C21···H8B^vii	3.0467	H21A···H17	2.4018
C21···H17	2.5118	H21B···H20B	2.0999
H1···C12	2.7268	H21B···N11^x	2.8833
H1···H12	2.1080	H21C···C17	2.7416
H1···C4^xii	2.9635	H21C···H17	2.2410
H1···C5^xii	3.0519	H21C···C17^iii	3.0881
H3···N11	2.7683
C5—O7—C8	118.19 (17)	C3—C4—H4	119.94
C16—N19—C20	120.66 (16)	C5—C4—H4	119.91
C16—N19—C21	121.10 (18)	C1—C6—H6	119.82
C20—N19—C21	117.63 (15)	C5—C6—H6	119.80
C2—C1—C6	121.83 (18)	O7—C8—H8A	109.50
C1—C2—C3	116.49 (16)	O7—C8—H8B	109.44
C1—C2—C9	122.32 (17)	O7—C8—H8C	109.46
C3—C2—C9	121.18 (17)	H8A—C8—H8B	109.44
C2—C3—C4	122.06 (18)	H8A—C8—H8C	109.52
C3—C4—C5	120.15 (18)	H8B—C8—H8C	109.46
O7—C5—C4	116.07 (17)	C9—C12—H12	114.00
O7—C5—C6	124.86 (17)	C13—C12—H12	114.00
C4—C5—C6	119.07 (16)	C13—C14—H14	118.68
C1—C6—C5	120.38 (18)	C15—C14—H14	118.66
C2—C9—C10	114.14 (16)	C14—C15—H15	119.54
C2—C9—C12	125.76 (17)	C16—C15—H15	119.47
C10—C9—C12	120.05 (16)	C16—C17—H17	119.14
N11—C10—C9	176.2 (2)	C18—C17—H17	119.26
C9—C12—C13	132.01 (19)	C13—C18—H18	118.75
C12—C13—C14	118.35 (18)	C17—C18—H18	118.79
C12—C13—C18	125.9 (2)	N19—C20—H20A	109.51
C14—C13—C18	115.71 (17)	N19—C20—H20B	109.47
C13—C14—C15	122.67 (19)	N19—C20—H20C	109.43
C14—C15—C16	121.0 (2)	H20A—C20—H20B	109.43
N19—C16—C15	122.18 (18)	H20A—C20—H20C	109.51
N19—C16—C17	121.27 (17)	H20B—C20—H20C	109.47
C15—C16—C17	116.54 (16)	N19—C21—H21A	109.43
C16—C17—C18	121.60 (19)	N19—C21—H21B	109.47
C13—C18—C17	122.5 (2)	N19—C21—H21C	109.49
C2—C1—H1	119.06	H21A—C21—H21B	109.48
C6—C1—H1	119.11	H21A—C21—H21C	109.45
C2—C3—H3	119.02	H21B—C21—H21C	109.50
C4—C3—H3	118.92
C8—O7—C5—C6	1.5 (3)	C3—C4—C5—O7	178.24 (17)
C8—O7—C5—C4	−177.73 (19)	C4—C5—C6—C1	1.1 (3)
C20—N19—C16—C17	−175.24 (17)	O7—C5—C6—C1	−178.14 (17)
C21—N19—C16—C17	−4.3 (3)	C10—C9—C12—C13	−1.4 (3)
C20—N19—C16—C15	4.3 (3)	C2—C9—C12—C13	−178.59 (19)
C21—N19—C16—C15	175.22 (17)	C9—C12—C13—C14	169.5 (2)
C6—C1—C2—C3	−1.0 (3)	C9—C12—C13—C18	−10.9 (3)
C2—C1—C6—C5	0.0 (3)	C12—C13—C18—C17	179.17 (17)
C6—C1—C2—C9	177.93 (17)	C12—C13—C14—C15	−178.96 (16)
C9—C2—C3—C4	−177.91 (17)	C14—C13—C18—C17	−1.3 (3)
C3—C2—C9—C12	179.52 (18)	C18—C13—C14—C15	1.5 (3)
C1—C2—C3—C4	1.1 (3)	C13—C14—C15—C16	−0.2 (3)
C1—C2—C9—C10	−176.72 (18)	C14—C15—C16—C17	−1.2 (2)
C3—C2—C9—C10	2.2 (3)	C14—C15—C16—N19	179.25 (16)
C1—C2—C9—C12	0.6 (3)	C15—C16—C17—C18	1.3 (3)
C2—C3—C4—C5	0.0 (3)	N19—C16—C17—C18	−179.07 (16)
C3—C4—C5—C6	−1.0 (3)	C16—C17—C18—C13	−0.1 (3)

Symmetry codes: (i) −x, −y, −z; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, y+1/2, −z+3/2; (iv) x, −y+1/2, z−1/2; (v) x−1, y, z−1; (vi) −x+1, −y, −z+1; (vii) x+1, y, z+1; (viii) −x, −y, −z+1; (ix) x, −y−1/2, z−1/2; (x) x, −y+1/2, z+1/2; (xi) −x+1, y−1/2, −z+3/2; (xii) −x, y−1/2, −z+1/2; (xiii) x, −y−1/2, z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···N11	0.93	2.61	3.419 (5)	146