(Z)-3-(3,4-Dimethoxy­phen­yl)-2-(4-methoxy­phen­yl)acrylonitrile

A new dipolarophile used in the construction of bioactive heterocycles, (Z)-3-(3,4-dimethoxy­phen­yl)-2-(4-methoxy­phen­yl)acrylonitrile, C₁₈H₁₇NO₃, has been synthesized by base-catalysed reaction of 3,4-dimethoxy­benzaldehyde with (4-methoxy­phen­yl)acetonitrile. The olefinic bond has Z geometry and the mol­ecules are linked by C—H...O and C—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.168
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.96

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C9     -   C10     ..       6.27 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

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Computing details

Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski and Minor, 1997) and SCALEPACK; 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.

(Z)-3-(3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylonitrile

Crystal data

C18H17NO3	F(000) = 624
Mr = 295.33	Dx = 1.299 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4731 reflections
a = 14.830 (9) Å	θ = 3.1–25.0°
b = 13.688 (7) Å	µ = 0.09 mm^−1
c = 7.445 (16) Å	T = 295 K
β = 91.724 (2)°	Block, pale yellow
V = 1511 (3) Å^3	0.25 × 0.20 × 0.20 mm
Z = 4

Data collection

MacScience DIPLabo 32001 diffractometer	1955 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 25.0°, θmin = 3.1°
Detector resolution: 10.0 pixels mm^-1	h = −17→17
ω scans	k = −15→14
4731 measured reflections	l = −8→8
2549 independent reflections

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)] = 0.054	H-atom parameters constrained
wR(F^2) = 0.168	w = 1/[σ^2(Fo^2) + (0.1039P)^2 + 0.2197P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2549 reflections	Δρmax = 0.20 e Å^−3
203 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (7)

Special details

Experimental. ¹H NMR (CDCl₃): δ 3.72 (s, 9H, O–CH₃), 6.79 (s, 2H, Ar–H), 7.4–7.55 (dd, 2H, Ar–H), 7.42 (s, 1H, CH═CH–Ar), 6.78–6.9 (dd, 2H, Ar–H).

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	0.12092 (10)	0.71841 (12)	0.4352 (2)	0.0760 (6)
O19	0.83848 (10)	0.71793 (11)	0.1178 (3)	0.0777 (6)
O21	0.90122 (10)	0.54153 (11)	0.1466 (2)	0.0770 (6)
N11	0.45805 (15)	0.37026 (16)	0.2334 (4)	0.0932 (10)
C1	0.27875 (14)	0.72289 (15)	0.4470 (3)	0.0614 (7)
C2	0.20035 (13)	0.67562 (15)	0.3877 (3)	0.0600 (7)
C3	0.20679 (14)	0.58931 (15)	0.2922 (3)	0.0633 (8)
C4	0.29052 (14)	0.55224 (14)	0.2559 (3)	0.0603 (7)
C5	0.36973 (13)	0.59872 (14)	0.3106 (3)	0.0563 (7)
C6	0.36176 (14)	0.68589 (15)	0.4089 (3)	0.0609 (7)
C8	0.03933 (15)	0.6837 (2)	0.3529 (4)	0.0833 (10)
C9	0.45922 (13)	0.55837 (14)	0.2701 (3)	0.0572 (7)
C10	0.46110 (15)	0.45365 (17)	0.2486 (3)	0.0671 (8)
C12	0.53402 (14)	0.61321 (15)	0.2537 (3)	0.0624 (7)
C13	0.62752 (14)	0.58760 (15)	0.2253 (3)	0.0593 (7)
C14	0.66327 (15)	0.49374 (15)	0.2418 (3)	0.0660 (8)
C15	0.75348 (15)	0.47681 (16)	0.2163 (3)	0.0649 (8)
C16	0.81094 (14)	0.55229 (14)	0.1739 (3)	0.0601 (7)
C17	0.77666 (14)	0.64765 (14)	0.1577 (3)	0.0602 (7)
C18	0.68688 (13)	0.66369 (15)	0.1838 (3)	0.0612 (7)
C20	0.81115 (16)	0.81736 (15)	0.1366 (4)	0.0778 (10)
C22	0.93850 (17)	0.44663 (19)	0.1746 (4)	0.0889 (10)
H1	0.27470	0.78030	0.51320	0.0740*
H3	0.15490	0.55660	0.25290	0.0760*
H4	0.29410	0.49390	0.19230	0.0720*
H6	0.41350	0.71880	0.44850	0.0730*
H8A	0.04360	0.68670	0.22470	0.1250*
H8B	−0.01000	0.72360	0.38970	0.1250*
H8C	0.02930	0.61730	0.38890	0.1250*
H12	0.52380	0.68010	0.26220	0.0750*
H14	0.62570	0.44190	0.27030	0.0790*
H15	0.77610	0.41370	0.22780	0.0780*
H18	0.66450	0.72700	0.17390	0.0730*
H20A	0.76060	0.83030	0.05650	0.1170*
H20B	0.86030	0.85970	0.10780	0.1170*
H20C	0.79420	0.82900	0.25820	0.1170*
H22A	0.92980	0.42680	0.29650	0.1330*
H22B	1.00180	0.44800	0.15170	0.1330*
H22C	0.90890	0.40110	0.09440	0.1330*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O7	0.0541 (9)	0.0844 (11)	0.0898 (12)	0.0003 (7)	0.0049 (8)	−0.0097 (8)
O19	0.0617 (10)	0.0600 (9)	0.1120 (14)	−0.0068 (7)	0.0127 (8)	−0.0030 (8)
O21	0.0561 (9)	0.0685 (10)	0.1067 (13)	0.0057 (7)	0.0061 (8)	−0.0033 (8)
N11	0.0857 (15)	0.0606 (15)	0.133 (2)	−0.0012 (10)	−0.0020 (13)	−0.0107 (11)
C1	0.0602 (13)	0.0615 (12)	0.0625 (13)	−0.0022 (9)	0.0024 (9)	−0.0057 (9)
C2	0.0523 (12)	0.0669 (13)	0.0611 (13)	−0.0011 (9)	0.0047 (9)	0.0047 (9)
C3	0.0603 (13)	0.0628 (12)	0.0666 (14)	−0.0091 (9)	−0.0035 (9)	0.0009 (9)
C4	0.0636 (13)	0.0554 (12)	0.0616 (13)	−0.0064 (8)	−0.0014 (9)	−0.0005 (8)
C5	0.0575 (12)	0.0553 (11)	0.0562 (12)	−0.0035 (8)	0.0021 (8)	0.0036 (8)
C6	0.0588 (12)	0.0630 (12)	0.0608 (13)	−0.0077 (9)	−0.0004 (9)	−0.0012 (9)
C8	0.0557 (14)	0.1024 (19)	0.0918 (19)	−0.0070 (12)	0.0014 (12)	−0.0013 (14)
C9	0.0593 (12)	0.0519 (12)	0.0603 (13)	−0.0003 (8)	0.0014 (9)	0.0011 (8)
C10	0.0598 (13)	0.0641 (15)	0.0772 (15)	−0.0004 (9)	0.0004 (10)	−0.0005 (10)
C12	0.0595 (12)	0.0597 (12)	0.0682 (14)	0.0002 (9)	0.0047 (9)	0.0059 (9)
C13	0.0567 (12)	0.0598 (12)	0.0614 (13)	0.0005 (8)	0.0040 (9)	0.0021 (8)
C14	0.0621 (13)	0.0627 (13)	0.0734 (14)	−0.0014 (9)	0.0061 (10)	0.0079 (10)
C15	0.0644 (13)	0.0603 (12)	0.0699 (14)	0.0038 (9)	0.0002 (10)	0.0027 (9)
C16	0.0553 (12)	0.0631 (12)	0.0617 (13)	0.0018 (8)	0.0006 (9)	−0.0039 (9)
C17	0.0578 (12)	0.0594 (12)	0.0636 (13)	−0.0036 (9)	0.0027 (9)	−0.0020 (9)
C18	0.0584 (12)	0.0565 (12)	0.0686 (14)	−0.0011 (8)	0.0019 (9)	0.0009 (9)
C20	0.0786 (16)	0.0581 (14)	0.0970 (19)	−0.0056 (10)	0.0073 (13)	0.0016 (11)
C22	0.0694 (16)	0.0804 (17)	0.117 (2)	0.0174 (12)	0.0063 (14)	0.0057 (14)

Geometric parameters (Å, º)

O7—C2	1.371 (4)	C15—C16	1.382 (4)
O7—C8	1.421 (4)	C16—C17	1.405 (4)
O19—C17	1.368 (4)	C17—C18	1.369 (4)
O19—C20	1.428 (4)	C1—H1	0.9305
O21—C16	1.368 (4)	C3—H3	0.9299
O21—C22	1.425 (4)	C4—H4	0.9307
N11—C10	1.148 (4)	C6—H6	0.9300
C1—C2	1.391 (4)	C8—H8A	0.9593
C1—C6	1.369 (4)	C8—H8B	0.9595
C2—C3	1.384 (4)	C8—H8C	0.9604
C3—C4	1.376 (4)	C12—H12	0.9305
C4—C5	1.386 (4)	C14—H14	0.9306
C5—C6	1.407 (4)	C15—H15	0.9297
C5—C9	1.477 (4)	C18—H18	0.9301
C9—C10	1.443 (4)	C20—H20A	0.9603
C9—C12	1.348 (4)	C20—H20B	0.9605
C12—C13	1.452 (4)	C20—H20C	0.9601
C13—C14	1.394 (4)	C22—H22A	0.9597
C13—C18	1.404 (4)	C22—H22B	0.9593
C14—C15	1.377 (4)	C22—H22C	0.9601
O7···C22^i	3.341 (8)	H3···C8	2.5681
O19···O21	2.594 (6)	H3···H8A	2.4329
O21···O19	2.594 (6)	H3···H8C	2.3018
O21···C8^ii	3.186 (7)	H4···C10	2.5594
O7···H22C^i	2.5479	H6···C12	2.7464
O7···H8A^iii	2.7921	H6···H12	2.2398
O19···H20C^iv	2.8117	H8A···C3	2.7952
O21···H8C^ii	2.7805	H8A···H3	2.4329
O21···H22B^v	2.6858	H8A···O7^iv	2.7921
N11···H14	2.6791	H8C···O21^viii	2.7805
N11···H12^vi	2.6169	H8C···C3	2.7762
N11···H18^vi	2.7749	H8C···H3	2.3018
C4···C15^vii	3.578 (8)	H8C···H22A^ix	2.4764
C8···O21^viii	3.186 (7)	H12···C6	2.6705
C10···C14	3.050 (7)	H12···H6	2.2398
C14···C10	3.050 (7)	H12···H18	2.2980
C15···C4^vii	3.578 (8)	H12···N11^i	2.6169
C22···O7^vi	3.341 (8)	H14···N11	2.6791
C22···C22^v	3.536 (9)	H14···C9	2.9389
C1···H15^i	3.0188	H14···C10	2.4468
C2···H1^iv	3.0885	H14···C6^ix	2.9617
C3···H1^iv	2.9394	H15···C22	2.4936
C3···H8C	2.7762	H15···H22A	2.3279
C3···H8A	2.7952	H15···H22C	2.2388
C4···H1^iv	2.9238	H15···C1^vi	3.0188
C5···H1^iv	3.0730	H18···C20	2.5245
C6···H14^ix	2.9617	H18···H12	2.2980
C6···H12	2.6705	H18···H20A	2.2066
C8···H3	2.5681	H18···H20C	2.4434
C8···H22A^ix	3.0395	H18···N11^i	2.7749
C8···H22C^i	3.0952	H20A···C18	2.7123
C9···H14	2.9389	H20A···H18	2.2066
C10···H4	2.5594	H20A···C17^iv	3.0010
C10···H14	2.4468	H20A···C18^iv	2.9527
C12···H6	2.7464	H20C···C18	2.8119
C15···H22A	2.7511	H20C···H18	2.4434
C15···H22C	2.7085	H20C···O19^iii	2.8117
C17···H20C^iv	3.0104	H20C···C17^iii	3.0104
C17···H20A^iii	3.0010	H22A···C15	2.7511
C18···H20C	2.8119	H22A···H15	2.3279
C18···H20A	2.7123	H22A···C8^ix	3.0395
C18···H20A^iii	2.9527	H22A···H8C^ix	2.4764
C20···H18	2.5245	H22B···O21^v	2.6858
C22···H15	2.4936	H22B···C22^v	2.9825
C22···H22B^v	2.9825	H22C···C15	2.7085
H1···C2^iii	3.0885	H22C···H15	2.2388
H1···C3^iii	2.9394	H22C···O7^vi	2.5479
H1···C4^iii	2.9238	H22C···C8^vi	3.0952
H1···C5^iii	3.0730
C2—O7—C8	118.21 (18)	C2—C3—H3	120.23
C17—O19—C20	117.06 (17)	C4—C3—H3	120.26
C16—O21—C22	116.98 (17)	C3—C4—H4	118.82
C2—C1—C6	120.7 (2)	C5—C4—H4	118.84
O7—C2—C1	115.83 (18)	C1—C6—H6	119.58
O7—C2—C3	124.77 (18)	C5—C6—H6	119.63
C1—C2—C3	119.36 (19)	O7—C8—H8A	109.50
C2—C3—C4	119.51 (19)	O7—C8—H8B	109.46
C3—C4—C5	122.34 (19)	O7—C8—H8C	109.45
C4—C5—C6	117.29 (18)	H8A—C8—H8B	109.48
C4—C5—C9	121.81 (18)	H8A—C8—H8C	109.49
C6—C5—C9	120.90 (18)	H8B—C8—H8C	109.46
C1—C6—C5	120.79 (19)	C9—C12—H12	113.93
C5—C9—C10	114.50 (17)	C13—C12—H12	113.94
C5—C9—C12	123.86 (18)	C13—C14—H14	119.61
C10—C9—C12	121.64 (19)	C15—C14—H14	119.61
N11—C10—C9	176.5 (2)	C14—C15—H15	119.55
C9—C12—C13	132.13 (19)	C16—C15—H15	119.50
C12—C13—C14	124.90 (19)	C13—C18—H18	118.94
C12—C13—C18	117.44 (18)	C17—C18—H18	118.97
C14—C13—C18	117.63 (19)	O19—C20—H20A	109.48
C13—C14—C15	120.8 (2)	O19—C20—H20B	109.49
C14—C15—C16	120.9 (2)	O19—C20—H20C	109.49
O21—C16—C15	124.50 (18)	H20A—C20—H20B	109.49
O21—C16—C17	116.14 (17)	H20A—C20—H20C	109.47
C15—C16—C17	119.36 (19)	H20B—C20—H20C	109.41
O19—C17—C16	115.41 (18)	O21—C22—H22A	109.49
O19—C17—C18	125.39 (18)	O21—C22—H22B	109.49
C16—C17—C18	119.20 (19)	O21—C22—H22C	109.43
C13—C18—C17	122.08 (19)	H22A—C22—H22B	109.49
C2—C1—H1	119.63	H22A—C22—H22C	109.42
C6—C1—H1	119.67	H22B—C22—H22C	109.49
C8—O7—C2—C1	169.1 (2)	C4—C5—C6—C1	−0.4 (3)
C8—O7—C2—C3	−13.0 (3)	C10—C9—C12—C13	−4.2 (4)
C20—O19—C17—C16	−167.4 (2)	C5—C9—C12—C13	175.9 (2)
C20—O19—C17—C18	11.9 (4)	C9—C12—C13—C14	−12.7 (4)
C22—O21—C16—C17	175.8 (2)	C9—C12—C13—C18	169.4 (2)
C22—O21—C16—C15	−3.8 (3)	C18—C13—C14—C15	−0.6 (3)
C6—C1—C2—O7	179.3 (2)	C14—C13—C18—C17	0.8 (3)
C6—C1—C2—C3	1.2 (3)	C12—C13—C18—C17	178.8 (2)
C2—C1—C6—C5	−0.7 (3)	C12—C13—C14—C15	−178.5 (2)
O7—C2—C3—C4	−178.5 (2)	C13—C14—C15—C16	0.1 (3)
C1—C2—C3—C4	−0.7 (3)	C14—C15—C16—O21	180.0 (2)
C2—C3—C4—C5	−0.5 (3)	C14—C15—C16—C17	0.4 (3)
C3—C4—C5—C6	1.0 (3)	O21—C16—C17—C18	−179.8 (2)
C3—C4—C5—C9	−179.7 (2)	C15—C16—C17—O19	179.2 (2)
C6—C5—C9—C10	152.1 (2)	O21—C16—C17—O19	−0.5 (3)
C4—C5—C9—C10	−27.1 (3)	C15—C16—C17—C18	−0.2 (3)
C6—C5—C9—C12	−28.0 (3)	O19—C17—C18—C13	−179.7 (2)
C9—C5—C6—C1	−179.7 (2)	C16—C17—C18—C13	−0.4 (3)
C4—C5—C9—C12	152.8 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N11^i	0.93	2.62	3.522 (8)	164
C22—H22C···O7^vi	0.96	2.55	3.341 (8)	140

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (vi) −x+1, y−1/2, −z+1/2.