4-Cyano-3-fluoro­phenyl (2E)-3-(4-heptyl­oxyphen­yl)acrylate

In the title compound, C₂₃H₂₄FNO₃, the two benzene rings are inclined to one another by 41.2 (1)°. The double bond shows a trans configuration. The crystal packing is stabilized by dipole-dipole and van der Waals inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.049
• wR factor = 0.137
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C2     ...       1.44 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            N   -C1  -C2  -C3    -95.00 13.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          2
            N   -C1  -C2  -C7     83.00 13.00   1.555   1.555   1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C23 H24 F N O3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

4-Cyano-3-fluorophenyl (2E)-3-(4-heptyloxyphenyl)acrylate

Crystal data

C23H24FNO3	Z = 2
Mr = 381.43	F(000) = 404
Triclinic, P1	Dx = 1.235 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5213 (14) Å	Cell parameters from 1979 reflections
b = 10.507 (2) Å	θ = 2.3–25.9°
c = 14.295 (3) Å	µ = 0.09 mm^−1
α = 74.252 (3)°	T = 293 K
β = 82.692 (3)°	Rod, colourless
γ = 70.764 (3)°	0.34 × 0.22 × 0.11 mm
V = 1025.7 (3) Å^3

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	3937 independent reflections
Radiation source: fine-focus sealed tube	2888 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
Detector resolution: 8.33 pixels mm^-1	θmax = 26.1°, θmin = 1.5°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→10
Tmin = 0.971, Tmax = 0.991	l = −14→17
5802 measured 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) = 0.137	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0633P)^2 + 0.1394P] where P = (Fo^2 + 2Fc^2)/3
3937 reflections	(Δ/σ)max = 0.001
253 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

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

	x	y	z	Uiso*/Ueq
F1	0.3982 (2)	1.19604 (12)	0.56655 (9)	0.0976 (4)
O1	0.2459 (2)	0.91338 (12)	0.85741 (8)	0.0698 (4)
O2	0.3770 (2)	0.68141 (12)	0.88045 (9)	0.0741 (4)
O3	0.19229 (19)	0.64546 (11)	1.48664 (8)	0.0658 (4)
N	0.2416 (3)	1.1312 (2)	0.37168 (13)	0.1033 (7)
C1	0.2515 (3)	1.0863 (2)	0.45340 (14)	0.0748 (6)
C2	0.2598 (3)	1.03129 (18)	0.55709 (12)	0.0616 (5)
C3	0.3283 (3)	1.09185 (17)	0.61256 (13)	0.0651 (5)
C4	0.3300 (3)	1.04916 (17)	0.71164 (12)	0.0652 (5)
H4A	0.3773	1.0917	0.7475	0.078*
C5	0.2600 (3)	0.94168 (17)	0.75648 (12)	0.0587 (4)
C6	0.1938 (3)	0.87515 (19)	0.70449 (13)	0.0670 (5)
H6A	0.1487	0.8014	0.7362	0.080*
C7	0.1956 (3)	0.9199 (2)	0.60445 (13)	0.0683 (5)
H7A	0.1533	0.8749	0.5684	0.082*
C8	0.3053 (2)	0.77946 (17)	0.91410 (12)	0.0563 (4)
C9	0.2678 (3)	0.78227 (18)	1.01575 (12)	0.0596 (4)
H9A	0.2127	0.8677	1.0312	0.071*
C10	0.3088 (2)	0.66810 (17)	1.08752 (11)	0.0550 (4)
H10A	0.3615	0.5841	1.0699	0.066*
C11	0.2798 (2)	0.66100 (16)	1.19116 (11)	0.0512 (4)
C12	0.2194 (2)	0.77993 (17)	1.22794 (12)	0.0585 (4)
H12A	0.1965	0.8671	1.1848	0.070*
C13	0.1934 (3)	0.77102 (17)	1.32545 (12)	0.0599 (4)
H13A	0.1546	0.8516	1.3478	0.072*
C14	0.2245 (2)	0.64230 (16)	1.39150 (11)	0.0528 (4)
C15	0.2852 (2)	0.52285 (17)	1.35719 (12)	0.0575 (4)
H15A	0.3076	0.4359	1.4006	0.069*
C16	0.3124 (2)	0.53355 (17)	1.25827 (12)	0.0558 (4)
H16A	0.3538	0.4528	1.2361	0.067*
C17	0.2252 (2)	0.51492 (17)	1.55778 (11)	0.0557 (4)
H17A	0.3554	0.4584	1.5520	0.067*
H17B	0.1449	0.4650	1.5470	0.067*
C18	0.1834 (3)	0.54146 (17)	1.65720 (11)	0.0571 (4)
H18A	0.0536	0.5990	1.6622	0.068*
H18B	0.2642	0.5914	1.6675	0.068*
C19	0.2152 (2)	0.40591 (16)	1.73492 (11)	0.0533 (4)
H19A	0.1345	0.3566	1.7234	0.064*
H19B	0.3447	0.3487	1.7285	0.064*
C20	0.1768 (3)	0.42306 (17)	1.83810 (11)	0.0573 (4)
H20A	0.2533	0.4756	1.8491	0.069*
H20B	0.0455	0.4762	1.8459	0.069*
C21	0.2182 (2)	0.28577 (17)	1.91388 (11)	0.0573 (4)
H21A	0.1391	0.2346	1.9036	0.069*
H21B	0.3483	0.2317	1.9045	0.069*
C22	0.1863 (3)	0.2997 (2)	2.01787 (12)	0.0696 (5)
H22A	0.2647	0.3513	2.0282	0.084*
H22B	0.0558	0.3528	2.0277	0.084*
C23	0.2300 (4)	0.1615 (2)	2.09236 (15)	0.0967 (7)
H23A	0.2066	0.1771	2.1566	0.145*
H23B	0.3600	0.1093	2.0844	0.145*
H23C	0.1513	0.1104	2.0834	0.145*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.1476 (12)	0.0710 (7)	0.0732 (8)	−0.0462 (8)	0.0079 (7)	−0.0066 (6)
O1	0.1069 (10)	0.0524 (7)	0.0415 (6)	−0.0135 (6)	−0.0037 (6)	−0.0113 (5)
O2	0.1033 (10)	0.0566 (7)	0.0524 (7)	−0.0090 (7)	−0.0047 (7)	−0.0158 (6)
O3	0.0921 (9)	0.0538 (7)	0.0401 (6)	−0.0125 (6)	0.0002 (6)	−0.0070 (5)
N	0.0905 (13)	0.1316 (17)	0.0526 (11)	−0.0031 (12)	−0.0044 (9)	−0.0035 (10)
C1	0.0661 (12)	0.0850 (13)	0.0522 (11)	−0.0009 (10)	−0.0032 (9)	−0.0098 (10)
C2	0.0623 (10)	0.0609 (10)	0.0463 (9)	−0.0006 (8)	−0.0026 (8)	−0.0110 (8)
C3	0.0821 (13)	0.0461 (9)	0.0546 (10)	−0.0104 (9)	0.0041 (9)	−0.0069 (8)
C4	0.0891 (13)	0.0486 (9)	0.0545 (10)	−0.0133 (9)	−0.0053 (9)	−0.0158 (8)
C5	0.0762 (11)	0.0462 (9)	0.0437 (9)	−0.0057 (8)	−0.0029 (8)	−0.0110 (7)
C6	0.0863 (13)	0.0622 (11)	0.0519 (10)	−0.0237 (9)	−0.0039 (9)	−0.0116 (8)
C7	0.0771 (13)	0.0741 (12)	0.0529 (10)	−0.0177 (10)	−0.0077 (9)	−0.0188 (9)
C8	0.0669 (11)	0.0529 (10)	0.0478 (9)	−0.0167 (8)	−0.0047 (8)	−0.0113 (7)
C9	0.0719 (11)	0.0566 (10)	0.0470 (9)	−0.0150 (8)	−0.0020 (8)	−0.0135 (8)
C10	0.0579 (10)	0.0577 (10)	0.0491 (9)	−0.0170 (8)	−0.0003 (7)	−0.0145 (8)
C11	0.0515 (9)	0.0537 (9)	0.0451 (9)	−0.0146 (7)	−0.0017 (7)	−0.0086 (7)
C12	0.0705 (11)	0.0480 (9)	0.0469 (9)	−0.0119 (8)	−0.0018 (8)	−0.0034 (7)
C13	0.0743 (11)	0.0472 (9)	0.0488 (9)	−0.0080 (8)	−0.0016 (8)	−0.0105 (7)
C14	0.0547 (9)	0.0538 (9)	0.0436 (9)	−0.0114 (7)	−0.0013 (7)	−0.0084 (7)
C15	0.0677 (11)	0.0477 (9)	0.0494 (9)	−0.0135 (8)	−0.0040 (8)	−0.0041 (7)
C16	0.0637 (10)	0.0507 (9)	0.0510 (9)	−0.0142 (8)	−0.0016 (8)	−0.0140 (7)
C17	0.0654 (10)	0.0531 (9)	0.0436 (9)	−0.0167 (8)	−0.0030 (7)	−0.0054 (7)
C18	0.0649 (10)	0.0548 (9)	0.0474 (9)	−0.0147 (8)	−0.0023 (8)	−0.0107 (7)
C19	0.0591 (10)	0.0539 (9)	0.0452 (9)	−0.0165 (8)	−0.0025 (7)	−0.0105 (7)
C20	0.0676 (11)	0.0575 (10)	0.0458 (9)	−0.0186 (8)	−0.0011 (8)	−0.0125 (7)
C21	0.0652 (11)	0.0606 (10)	0.0461 (9)	−0.0217 (8)	−0.0014 (8)	−0.0104 (7)
C22	0.0865 (13)	0.0759 (12)	0.0466 (10)	−0.0293 (10)	−0.0016 (9)	−0.0105 (9)
C23	0.122 (2)	0.1042 (17)	0.0533 (12)	−0.0399 (15)	−0.0079 (12)	0.0050 (11)

Geometric parameters (Å, º)

F1—C3	1.345 (2)	C13—H13A	0.9300
O1—C8	1.3767 (19)	C14—C15	1.387 (2)
O1—C5	1.3893 (19)	C15—C16	1.382 (2)
O2—C8	1.1920 (19)	C15—H15A	0.9300
O3—C14	1.3583 (19)	C16—H16A	0.9300
O3—C17	1.4352 (18)	C17—C18	1.497 (2)
N—C1	1.137 (2)	C17—H17A	0.9700
C1—C2	1.439 (2)	C17—H17B	0.9700
C2—C3	1.376 (3)	C18—C19	1.518 (2)
C2—C7	1.386 (3)	C18—H18A	0.9700
C3—C4	1.365 (2)	C18—H18B	0.9700
C4—C5	1.370 (2)	C19—C20	1.514 (2)
C4—H4A	0.9300	C19—H19A	0.9700
C5—C6	1.377 (3)	C19—H19B	0.9700
C6—C7	1.378 (2)	C20—C21	1.514 (2)
C6—H6A	0.9300	C20—H20A	0.9700
C7—H7A	0.9300	C20—H20B	0.9700
C8—C9	1.451 (2)	C21—C22	1.514 (2)
C9—C10	1.325 (2)	C21—H21A	0.9700
C9—H9A	0.9300	C21—H21B	0.9700
C10—C11	1.455 (2)	C22—C23	1.512 (3)
C10—H10A	0.9300	C22—H22A	0.9700
C11—C16	1.386 (2)	C22—H22B	0.9700
C11—C12	1.402 (2)	C23—H23A	0.9600
C12—C13	1.365 (2)	C23—H23B	0.9600
C12—H12A	0.9300	C23—H23C	0.9600
C13—C14	1.389 (2)
C8—O1—C5	121.53 (13)	C15—C16—C11	121.98 (15)
C14—O3—C17	117.63 (13)	C15—C16—H16A	119.0
N—C1—C2	178.8 (2)	C11—C16—H16A	119.0
C3—C2—C7	118.02 (16)	O3—C17—C18	109.07 (13)
C3—C2—C1	120.01 (18)	O3—C17—H17A	109.9
C7—C2—C1	121.95 (18)	C18—C17—H17A	109.9
F1—C3—C4	119.14 (17)	O3—C17—H17B	109.9
F1—C3—C2	118.19 (16)	C18—C17—H17B	109.9
C4—C3—C2	122.66 (18)	H17A—C17—H17B	108.3
C3—C4—C5	117.88 (17)	C17—C18—C19	110.88 (13)
C3—C4—H4A	121.1	C17—C18—H18A	109.5
C5—C4—H4A	121.1	C19—C18—H18A	109.5
C4—C5—C6	121.93 (16)	C17—C18—H18B	109.5
C4—C5—O1	115.14 (15)	C19—C18—H18B	109.5
C6—C5—O1	122.70 (17)	H18A—C18—H18B	108.1
C5—C6—C7	118.75 (18)	C20—C19—C18	114.44 (14)
C5—C6—H6A	120.6	C20—C19—H19A	108.7
C7—C6—H6A	120.6	C18—C19—H19A	108.7
C6—C7—C2	120.71 (17)	C20—C19—H19B	108.7
C6—C7—H7A	119.6	C18—C19—H19B	108.7
C2—C7—H7A	119.6	H19A—C19—H19B	107.6
O2—C8—O1	122.62 (15)	C21—C20—C19	113.06 (14)
O2—C8—C9	128.38 (16)	C21—C20—H20A	109.0
O1—C8—C9	109.00 (14)	C19—C20—H20A	109.0
C10—C9—C8	122.68 (16)	C21—C20—H20B	109.0
C10—C9—H9A	118.7	C19—C20—H20B	109.0
C8—C9—H9A	118.7	H20A—C20—H20B	107.8
C9—C10—C11	126.52 (16)	C22—C21—C20	114.23 (15)
C9—C10—H10A	116.7	C22—C21—H21A	108.7
C11—C10—H10A	116.7	C20—C21—H21A	108.7
C16—C11—C12	117.06 (15)	C22—C21—H21B	108.7
C16—C11—C10	120.38 (15)	C20—C21—H21B	108.7
C12—C11—C10	122.56 (14)	H21A—C21—H21B	107.6
C13—C12—C11	121.65 (15)	C23—C22—C21	113.39 (17)
C13—C12—H12A	119.2	C23—C22—H22A	108.9
C11—C12—H12A	119.2	C21—C22—H22A	108.9
C12—C13—C14	120.40 (16)	C23—C22—H22B	108.9
C12—C13—H13A	119.8	C21—C22—H22B	108.9
C14—C13—H13A	119.8	H22A—C22—H22B	107.7
O3—C14—C15	125.27 (14)	C22—C23—H23A	109.5
O3—C14—C13	115.54 (14)	C22—C23—H23B	109.5
C15—C14—C13	119.20 (15)	H23A—C23—H23B	109.5
C16—C15—C14	119.71 (15)	C22—C23—H23C	109.5
C16—C15—H15A	120.1	H23A—C23—H23C	109.5
C14—C15—H15A	120.1	H23B—C23—H23C	109.5
N—C1—C2—C3	−95 (13)	C8—C9—C10—C11	178.75 (15)
N—C1—C2—C7	83 (13)	C9—C10—C11—C16	173.74 (17)
C7—C2—C3—F1	177.19 (16)	C9—C10—C11—C12	−6.5 (3)
C1—C2—C3—F1	−4.6 (3)	C16—C11—C12—C13	−0.1 (3)
C7—C2—C3—C4	−1.9 (3)	C10—C11—C12—C13	−179.86 (16)
C1—C2—C3—C4	176.31 (17)	C11—C12—C13—C14	−0.7 (3)
F1—C3—C4—C5	−179.22 (16)	C17—O3—C14—C15	0.6 (3)
C2—C3—C4—C5	−0.1 (3)	C17—O3—C14—C13	−179.06 (15)
C3—C4—C5—C6	1.6 (3)	C12—C13—C14—O3	−179.26 (15)
C3—C4—C5—O1	−173.04 (15)	C12—C13—C14—C15	1.0 (3)
C8—O1—C5—C4	−134.56 (17)	O3—C14—C15—C16	179.83 (16)
C8—O1—C5—C6	50.8 (2)	C13—C14—C15—C16	−0.5 (3)
C4—C5—C6—C7	−1.0 (3)	C14—C15—C16—C11	−0.4 (3)
O1—C5—C6—C7	173.22 (16)	C12—C11—C16—C15	0.7 (3)
C5—C6—C7—C2	−1.1 (3)	C10—C11—C16—C15	−179.59 (15)
C3—C2—C7—C6	2.5 (3)	C14—O3—C17—C18	179.45 (14)
C1—C2—C7—C6	−175.69 (17)	O3—C17—C18—C19	179.61 (13)
C5—O1—C8—O2	2.4 (3)	C17—C18—C19—C20	179.78 (14)
C5—O1—C8—C9	−178.32 (15)	C18—C19—C20—C21	−177.42 (14)
O2—C8—C9—C10	−1.3 (3)	C19—C20—C21—C22	178.36 (15)
O1—C8—C9—C10	179.50 (16)	C20—C21—C22—C23	−179.49 (17)