1-(4-Fluoro­phen­yl)-3-(2,4,5-trimethoxy­phen­yl)prop-2-en-1-one

Teh, J.B.-J.; Patil, P.S.; Fun, H.-K.; Razak, I.A.; Dharmaprakash, S.M.

doi:10.1107/S160053680605063X

1-(4-Fluorophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one

J. B.-J. Teh, P. S. Patil, H.-K. Fun, I. A. Razak and S. M. Dharmaprakash

In the title compound, C₁₈H₁₇FO₄, the dihedral angle between the benzene rings is 12.42 (2)°. The crystal structure is stabilized by C—H

O, C—H

π and π–π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680605063X/sj2180sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680605063X/sj2180Isup2.hkl Contains datablock I

CCDC reference: 634002

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.001 Å
R factor = 0.040
wR factor = 0.123
Data-to-parameter ratio = 25.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) .         20 Ang.
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.10

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

   2 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); 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).

1-(4-Fluorophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₈H₁₇FO₄	Z = 2
M_r = 316.32	F(000) = 332
Triclinic, P1	D_x = 1.437 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5325 (2) Å	Cell parameters from 6193 reflections
b = 8.8404 (2) Å	θ = 2.1–32.5°
c = 10.1468 (2) Å	µ = 0.11 mm⁻¹
α = 87.048 (1)°	T = 100 K
β = 73.313 (1)°	Block, yellow
γ = 85.919 (1)°	0.52 × 0.52 × 0.51 mm
V = 730.90 (3) Å³

Data collection top

Bruker SMART APEX2 CCD diffractometer	5266 independent reflections
Radiation source: fine-focus sealed tube	4726 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 8.33 pixels mm^-1	θ_max = 32.5°, θ_min = 2.1°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
T_min = 0.935, T_max = 0.946	l = −14→15
18180 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0739P)² + 0.1553P] where P = (F_o² + 2F_c²)/3
5266 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.91205 (7)	0.27494 (8)	0.52013 (7)	0.03012 (15)
O1	0.29214 (8)	0.39667 (7)	0.30815 (7)	0.02026 (13)
O2	0.04143 (7)	0.68679 (7)	0.02825 (7)	0.01908 (13)
O3	0.29784 (7)	1.08381 (7)	−0.29340 (6)	0.01864 (13)
O4	0.57204 (7)	1.01833 (7)	−0.23947 (6)	0.01902 (13)
C1	0.69568 (10)	0.50196 (9)	0.31411 (8)	0.01706 (14)
H1A	0.7078	0.5897	0.2584	0.020*
C2	0.81770 (10)	0.45281 (10)	0.37523 (9)	0.01934 (15)
H2A	0.9122	0.5055	0.3600	0.023*
C3	0.79425 (10)	0.32319 (10)	0.45934 (9)	0.01956 (16)
C4	0.65617 (11)	0.24121 (10)	0.48521 (8)	0.01937 (15)
H4A	0.6432	0.1556	0.5437	0.023*
C5	0.53743 (10)	0.29054 (9)	0.42124 (8)	0.01659 (14)
H5A	0.4445	0.2358	0.4357	0.020*
C6	0.55467 (9)	0.42088 (8)	0.33543 (7)	0.01401 (13)
C7	0.41811 (10)	0.46668 (9)	0.27395 (8)	0.01475 (14)
C8	0.43671 (10)	0.59369 (9)	0.17135 (8)	0.01640 (14)
H8A	0.5300	0.6490	0.1488	0.020*
C9	0.31695 (9)	0.62835 (9)	0.11098 (8)	0.01476 (14)
H9A	0.2247	0.5719	0.1416	0.018*
C10	0.31405 (9)	0.74315 (8)	0.00374 (8)	0.01387 (13)
C11	0.16957 (9)	0.77412 (9)	−0.03503 (8)	0.01415 (13)
C12	0.15849 (9)	0.88987 (9)	−0.13193 (8)	0.01476 (14)
H12A	0.0601	0.9123	−0.1531	0.018*
C13	0.29475 (9)	0.97125 (9)	−0.19648 (8)	0.01413 (14)
C14	0.44441 (9)	0.93665 (9)	−0.16461 (8)	0.01427 (14)
C15	0.45130 (9)	0.82633 (9)	−0.06458 (8)	0.01460 (14)
H15A	0.5489	0.8063	−0.0416	0.018*
C16	−0.09566 (10)	0.69496 (9)	−0.02582 (9)	0.01811 (15)
H16A	−0.1648	0.6135	0.0136	0.027*
H16B	−0.0580	0.6866	−0.1240	0.027*
H16C	−0.1566	0.7903	−0.0035	0.027*
C17	0.15215 (10)	1.11696 (10)	−0.33490 (9)	0.01898 (15)
H17A	0.1717	1.1943	−0.4067	0.028*
H17B	0.0649	1.1520	−0.2576	0.028*
H17C	0.1220	1.0269	−0.3682	0.028*
C18	0.73204 (10)	0.96730 (10)	−0.23273 (9)	0.01910 (15)
H18A	0.8122	1.0245	−0.2985	0.029*
H18B	0.7511	0.8616	−0.2532	0.029*
H18C	0.7405	0.9815	−0.1419	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0253 (3)	0.0369 (3)	0.0332 (3)	0.0025 (2)	−0.0194 (2)	0.0099 (2)
O1	0.0184 (3)	0.0210 (3)	0.0233 (3)	−0.0047 (2)	−0.0090 (2)	0.0045 (2)
O2	0.0142 (2)	0.0217 (3)	0.0234 (3)	−0.0056 (2)	−0.0091 (2)	0.0088 (2)
O3	0.0148 (3)	0.0204 (3)	0.0228 (3)	−0.0026 (2)	−0.0102 (2)	0.0098 (2)
O4	0.0130 (2)	0.0222 (3)	0.0238 (3)	−0.0048 (2)	−0.0092 (2)	0.0099 (2)
C1	0.0186 (3)	0.0179 (3)	0.0165 (3)	−0.0019 (3)	−0.0085 (3)	0.0031 (2)
C2	0.0178 (3)	0.0226 (4)	0.0197 (3)	−0.0016 (3)	−0.0092 (3)	0.0026 (3)
C3	0.0191 (3)	0.0238 (4)	0.0177 (3)	0.0042 (3)	−0.0100 (3)	0.0017 (3)
C4	0.0220 (4)	0.0195 (3)	0.0169 (3)	0.0019 (3)	−0.0076 (3)	0.0042 (3)
C5	0.0179 (3)	0.0173 (3)	0.0145 (3)	−0.0005 (3)	−0.0051 (2)	0.0027 (2)
C6	0.0156 (3)	0.0149 (3)	0.0124 (3)	0.0003 (2)	−0.0058 (2)	0.0009 (2)
C7	0.0168 (3)	0.0145 (3)	0.0140 (3)	0.0001 (2)	−0.0065 (2)	0.0005 (2)
C8	0.0159 (3)	0.0183 (3)	0.0159 (3)	−0.0019 (2)	−0.0065 (2)	0.0043 (2)
C9	0.0159 (3)	0.0148 (3)	0.0147 (3)	−0.0013 (2)	−0.0063 (2)	0.0016 (2)
C10	0.0146 (3)	0.0137 (3)	0.0150 (3)	−0.0010 (2)	−0.0072 (2)	0.0018 (2)
C11	0.0130 (3)	0.0147 (3)	0.0158 (3)	−0.0014 (2)	−0.0061 (2)	0.0020 (2)
C12	0.0128 (3)	0.0155 (3)	0.0169 (3)	−0.0001 (2)	−0.0066 (2)	0.0029 (2)
C13	0.0136 (3)	0.0147 (3)	0.0153 (3)	−0.0003 (2)	−0.0068 (2)	0.0028 (2)
C14	0.0127 (3)	0.0154 (3)	0.0163 (3)	−0.0022 (2)	−0.0069 (2)	0.0022 (2)
C15	0.0142 (3)	0.0155 (3)	0.0162 (3)	−0.0013 (2)	−0.0081 (2)	0.0022 (2)
C16	0.0134 (3)	0.0204 (3)	0.0224 (3)	−0.0030 (3)	−0.0083 (3)	0.0029 (3)
C17	0.0151 (3)	0.0211 (4)	0.0227 (4)	0.0001 (3)	−0.0102 (3)	0.0063 (3)
C18	0.0131 (3)	0.0225 (4)	0.0234 (4)	−0.0031 (3)	−0.0084 (3)	0.0049 (3)

Geometric parameters (Å, º) top

F1—C3	1.3567 (9)	C8—H8A	0.9300
O1—C7	1.2317 (10)	C9—C10	1.4535 (10)
O2—C11	1.3673 (9)	C9—H9A	0.9300
O2—C16	1.4237 (10)	C10—C11	1.4032 (10)
O3—C13	1.3586 (9)	C10—C15	1.4130 (10)
O3—C17	1.4299 (9)	C11—C12	1.3996 (10)
O4—C14	1.3656 (9)	C12—C13	1.3898 (10)
O4—C18	1.4264 (10)	C12—H12A	0.9300
C1—C2	1.3915 (11)	C13—C14	1.4142 (10)
C1—C6	1.4020 (11)	C14—C15	1.3817 (10)
C1—H1A	0.9300	C15—H15A	0.9300
C2—C3	1.3839 (12)	C16—H16A	0.9600
C2—H2A	0.9300	C16—H16B	0.9600
C3—C4	1.3808 (13)	C16—H16C	0.9600
C4—C5	1.3869 (11)	C17—H17A	0.9600
C4—H4A	0.9300	C17—H17B	0.9600
C5—C6	1.3981 (10)	C17—H17C	0.9600
C5—H5A	0.9300	C18—H18A	0.9600
C6—C7	1.4950 (11)	C18—H18B	0.9600
C7—C8	1.4764 (11)	C18—H18C	0.9600
C8—C9	1.3449 (10)

C11—O2—C16	117.88 (6)	O2—C11—C12	122.50 (7)
C13—O3—C17	117.50 (6)	O2—C11—C10	116.34 (7)
C14—O4—C18	117.12 (6)	C12—C11—C10	121.15 (7)
C2—C1—C6	120.85 (7)	C13—C12—C11	119.87 (7)
C2—C1—H1A	119.6	C13—C12—H12A	120.1
C6—C1—H1A	119.6	C11—C12—H12A	120.1
C3—C2—C1	118.00 (8)	O3—C13—C12	124.56 (7)
C3—C2—H2A	121.0	O3—C13—C14	115.43 (6)
C1—C2—H2A	121.0	C12—C13—C14	120.00 (7)
F1—C3—C4	118.40 (7)	O4—C14—C15	125.78 (7)
F1—C3—C2	118.43 (8)	O4—C14—C13	114.88 (7)
C4—C3—C2	123.17 (7)	C15—C14—C13	119.33 (7)
C3—C4—C5	117.90 (7)	C14—C15—C10	121.75 (7)
C3—C4—H4A	121.0	C14—C15—H15A	119.1
C5—C4—H4A	121.0	C10—C15—H15A	119.1
C4—C5—C6	121.32 (7)	O2—C16—H16A	109.5
C4—C5—H5A	119.3	O2—C16—H16B	109.5
C6—C5—H5A	119.3	H16A—C16—H16B	109.5
C5—C6—C1	118.74 (7)	O2—C16—H16C	109.5
C5—C6—C7	117.24 (7)	H16A—C16—H16C	109.5
C1—C6—C7	124.01 (7)	H16B—C16—H16C	109.5
O1—C7—C8	120.73 (7)	O3—C17—H17A	109.5
O1—C7—C6	119.59 (7)	O3—C17—H17B	109.5
C8—C7—C6	119.67 (7)	H17A—C17—H17B	109.5
C9—C8—C7	119.15 (7)	O3—C17—H17C	109.5
C9—C8—H8A	120.4	H17A—C17—H17C	109.5
C7—C8—H8A	120.4	H17B—C17—H17C	109.5
C8—C9—C10	127.98 (7)	O4—C18—H18A	109.5
C8—C9—H9A	116.0	O4—C18—H18B	109.5
C10—C9—H9A	116.0	H18A—C18—H18B	109.5
C11—C10—C15	117.74 (7)	O4—C18—H18C	109.5
C11—C10—C9	119.33 (7)	H18A—C18—H18C	109.5
C15—C10—C9	122.93 (7)	H18B—C18—H18C	109.5

C6—C1—C2—C3	−1.07 (12)	C15—C10—C11—O2	176.97 (7)
C1—C2—C3—F1	−179.57 (7)	C9—C10—C11—O2	−2.97 (11)
C1—C2—C3—C4	−0.07 (13)	C15—C10—C11—C12	−3.88 (11)
F1—C3—C4—C5	−179.26 (7)	C9—C10—C11—C12	176.17 (7)
C2—C3—C4—C5	1.24 (13)	O2—C11—C12—C13	−177.69 (7)
C3—C4—C5—C6	−1.31 (12)	C10—C11—C12—C13	3.22 (12)
C4—C5—C6—C1	0.23 (11)	C17—O3—C13—C12	−2.21 (12)
C4—C5—C6—C7	−178.60 (7)	C17—O3—C13—C14	176.47 (7)
C2—C1—C6—C5	0.99 (12)	C11—C12—C13—O3	178.87 (7)
C2—C1—C6—C7	179.73 (7)	C11—C12—C13—C14	0.25 (11)
C5—C6—C7—O1	5.38 (11)	C18—O4—C14—C15	12.27 (12)
C1—C6—C7—O1	−173.38 (8)	C18—O4—C14—C13	−167.30 (7)
C5—C6—C7—C8	−173.66 (7)	O3—C13—C14—O4	−2.06 (10)
C1—C6—C7—C8	7.58 (11)	C12—C13—C14—O4	176.68 (7)
O1—C7—C8—C9	−2.77 (12)	O3—C13—C14—C15	178.33 (7)
C6—C7—C8—C9	176.26 (7)	C12—C13—C14—C15	−2.92 (11)
C7—C8—C9—C10	−176.86 (7)	O4—C14—C15—C10	−177.35 (7)
C8—C9—C10—C11	−172.71 (8)	C13—C14—C15—C10	2.21 (12)
C8—C9—C10—C15	7.35 (13)	C11—C10—C15—C14	1.14 (11)
C16—O2—C11—C12	12.28 (11)	C9—C10—C15—C14	−178.91 (7)
C16—O2—C11—C10	−168.59 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18C···Cgⁱ	0.96	2.80	3.693 (1)	155
C4—H4A···O4ⁱⁱ	0.93	2.40	3.269 (1)	156
C5—H5A···O1	0.93	2.43	2.751 (1)	100
C9—H9A···O1	0.93	2.40	2.764 (1)	103
C9—H9A···O2	0.93	2.34	2.723 (1)	104
C18—H18B···O1ⁱⁱⁱ	0.96	2.46	3.379 (1)	161

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

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1-(4-Fluoro­phen­yl)-3-(2,4,5-trimethoxy­phen­yl)prop-2-en-1-one

Supporting information

Key indicators

checkCIF/PLATON results

1-(4-Fluorophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one