(E)-1-(4-Fluoro-2-hy­droxy­phen­yl)-3-(2,3,4-tri­meth­oxy­phen­yl)prop-2-en-1-one

In the title mol­ecule, C₁₈H₁₇FO₅, the conformation about the C=C bond of the central enone group is trans. The dihedral angle between the benzene rings is 13.08 (3)°. The hy­droxy group attached to the benzene ring is involved in an intra­molecular O—H...O hydrogen bond. In the crystal, weak C—H...O hydrogen bonds link the mol­ecules into chains along [001].

Key indicators

• Single-crystal X-ray study
• T = 223 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.125
• Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.134 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          9 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

(E)-1-(4-Fluoro-2-hydroxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one

Crystal data

C18H17FO5	F(000) = 696
Mr = 332.32	Dx = 1.411 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.5801 (12) Å	Cell parameters from 9964 reflections
b = 8.3414 (6) Å	θ = 2.8–25.8°
c = 12.1298 (8) Å	µ = 0.11 mm^−1
β = 97.086 (3)°	T = 223 K
V = 1564.35 (19) Å^3	Block, yellow
Z = 4	0.21 × 0.15 × 0.10 mm

Data collection

PHOTON 100 CMOS diffractometer	2539 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.079
Absorption correction: multi-scan (SADABS; Bruker, 2012)	θmax = 28.4°, θmin = 2.6°
Tmin = 0.706, Tmax = 0.746	h = −20→20
64701 measured reflections	k = −11→11
3904 independent reflections	l = −16→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0473P)^2 + 0.6183P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
3904 reflections	Δρmax = 0.21 e Å^−3
221 parameters	Δρmin = −0.21 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
O1	0.92429 (10)	0.0434 (2)	0.67173 (13)	0.0787 (5)
C1	0.95147 (12)	0.1327 (2)	0.60215 (15)	0.0465 (4)
C2	0.89787 (11)	0.1589 (2)	0.49622 (15)	0.0448 (4)
H2	0.9178	0.2247	0.4418	0.054*
C3	0.82032 (11)	0.0890 (2)	0.47693 (15)	0.0433 (4)
H3	0.8031	0.0297	0.5363	0.052*
C4	0.75915 (10)	0.0924 (2)	0.37646 (14)	0.0406 (4)
C5	0.67961 (11)	0.01064 (19)	0.37400 (14)	0.0387 (4)
C6	0.62259 (10)	0.00211 (19)	0.27734 (14)	0.0384 (4)
C7	0.64306 (11)	0.0776 (2)	0.18080 (15)	0.0415 (4)
C8	0.71985 (12)	0.1619 (2)	0.18280 (16)	0.0487 (4)
H8	0.7334	0.2144	0.1186	0.058*
C9	0.77632 (11)	0.1685 (2)	0.27966 (15)	0.0473 (4)
H9	0.8281	0.2263	0.2802	0.057*
O2	0.65803 (8)	−0.04848 (15)	0.47252 (10)	0.0482 (3)
C10	0.63936 (14)	−0.2150 (2)	0.47998 (17)	0.0563 (5)
H10A	0.5893	−0.2413	0.4275	0.084*
H10B	0.6274	−0.2400	0.5547	0.084*
H10C	0.6887	−0.2770	0.4629	0.084*
O3	0.54649 (7)	−0.08295 (14)	0.27272 (10)	0.0439 (3)
C11	0.47618 (11)	0.0049 (2)	0.30660 (18)	0.0553 (5)
H11A	0.4884	0.0307	0.3849	0.083*
H11B	0.4239	−0.0591	0.2942	0.083*
H11C	0.4682	0.1032	0.2638	0.083*
O4	0.58278 (8)	0.06284 (15)	0.09020 (10)	0.0483 (3)
C12	0.59864 (13)	0.1441 (2)	−0.00904 (16)	0.0544 (5)
H12A	0.6038	0.2583	0.0054	0.082*
H12B	0.5510	0.1248	−0.0669	0.082*
H12C	0.6519	0.1045	−0.0330	0.082*
C13	1.03648 (11)	0.2090 (2)	0.62893 (14)	0.0396 (4)
C14	1.08778 (12)	0.1692 (2)	0.72906 (14)	0.0458 (4)
C15	1.16780 (12)	0.2411 (2)	0.75754 (16)	0.0520 (5)
H15	1.2027	0.2136	0.8237	0.062*
C16	1.19430 (12)	0.3521 (2)	0.68738 (17)	0.0524 (5)
C17	1.14761 (12)	0.3949 (2)	0.58816 (17)	0.0511 (5)
H17	1.1687	0.4717	0.5415	0.061*
C18	1.06905 (11)	0.3214 (2)	0.55947 (15)	0.0444 (4)
H18	1.0364	0.3474	0.4914	0.053*
O5	1.06213 (10)	0.06119 (19)	0.80053 (11)	0.0663 (4)
H5	1.0118	0.0325	0.7789	0.099*
F1	1.27125 (7)	0.42519 (16)	0.71683 (12)	0.0763 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0693 (10)	0.1025 (13)	0.0620 (9)	−0.0386 (9)	−0.0006 (7)	0.0286 (9)
C1	0.0466 (10)	0.0478 (10)	0.0461 (10)	−0.0059 (8)	0.0095 (8)	−0.0009 (8)
C2	0.0420 (10)	0.0458 (10)	0.0476 (10)	−0.0037 (8)	0.0097 (8)	−0.0011 (8)
C3	0.0438 (10)	0.0410 (9)	0.0466 (10)	−0.0025 (8)	0.0109 (8)	−0.0047 (8)
C4	0.0382 (9)	0.0350 (9)	0.0497 (10)	−0.0018 (7)	0.0098 (7)	−0.0059 (7)
C5	0.0398 (9)	0.0323 (8)	0.0457 (9)	0.0000 (7)	0.0116 (7)	−0.0026 (7)
C6	0.0351 (8)	0.0303 (8)	0.0513 (10)	−0.0026 (7)	0.0113 (7)	−0.0024 (7)
C7	0.0404 (9)	0.0342 (9)	0.0500 (10)	−0.0004 (7)	0.0058 (8)	−0.0004 (7)
C8	0.0493 (11)	0.0470 (10)	0.0511 (11)	−0.0080 (8)	0.0114 (8)	0.0073 (8)
C9	0.0407 (10)	0.0451 (10)	0.0573 (11)	−0.0096 (8)	0.0101 (8)	−0.0002 (8)
O2	0.0555 (8)	0.0440 (7)	0.0476 (7)	−0.0117 (6)	0.0156 (6)	−0.0007 (6)
C10	0.0649 (13)	0.0420 (10)	0.0631 (12)	0.0024 (9)	0.0129 (10)	0.0091 (9)
O3	0.0372 (6)	0.0367 (6)	0.0587 (8)	−0.0067 (5)	0.0099 (5)	−0.0018 (5)
C11	0.0367 (10)	0.0583 (12)	0.0718 (13)	0.0030 (9)	0.0097 (9)	0.0003 (10)
O4	0.0483 (7)	0.0467 (7)	0.0491 (7)	−0.0092 (6)	0.0029 (6)	0.0060 (6)
C12	0.0595 (12)	0.0532 (12)	0.0501 (11)	−0.0050 (9)	0.0055 (9)	0.0075 (9)
C13	0.0403 (9)	0.0390 (9)	0.0408 (9)	−0.0008 (7)	0.0104 (7)	−0.0068 (7)
C14	0.0506 (11)	0.0470 (10)	0.0405 (9)	−0.0006 (8)	0.0083 (8)	−0.0064 (8)
C15	0.0484 (11)	0.0561 (12)	0.0495 (10)	0.0023 (9)	−0.0015 (9)	−0.0126 (9)
C16	0.0375 (10)	0.0525 (11)	0.0670 (13)	−0.0040 (8)	0.0058 (9)	−0.0188 (10)
C17	0.0444 (10)	0.0472 (10)	0.0637 (12)	−0.0054 (8)	0.0147 (9)	−0.0005 (9)
C18	0.0407 (9)	0.0450 (10)	0.0482 (10)	−0.0003 (8)	0.0088 (8)	−0.0002 (8)
O5	0.0720 (10)	0.0787 (10)	0.0467 (8)	−0.0169 (8)	0.0016 (7)	0.0116 (7)
F1	0.0467 (7)	0.0820 (9)	0.0978 (10)	−0.0187 (6)	−0.0004 (6)	−0.0190 (8)

Geometric parameters (Å, º)

O1—C1	1.239 (2)	C10—H10C	0.9700
C1—O1	1.239 (2)	O3—C11	1.420 (2)
C1—C2	1.460 (3)	C11—H11A	0.9700
C1—C13	1.469 (2)	C11—H11B	0.9700
C2—C3	1.336 (2)	C11—H11C	0.9700
C2—H2	0.9400	O4—C12	1.429 (2)
C3—C4	1.452 (2)	C12—H12A	0.9700
C3—H3	0.9400	C12—H12B	0.9700
C4—C9	1.389 (2)	C12—H12C	0.9700
C4—C5	1.412 (2)	C13—C18	1.397 (2)
C5—O2	1.372 (2)	C13—C14	1.409 (2)
C5—C6	1.383 (2)	C14—O5	1.345 (2)
C6—O3	1.3768 (19)	C14—C15	1.388 (3)
C6—C7	1.400 (2)	C15—C16	1.356 (3)
C7—O4	1.360 (2)	C15—H15	0.9400
C7—C8	1.386 (2)	C16—F1	1.353 (2)
C8—C9	1.379 (3)	C16—C17	1.374 (3)
C8—H8	0.9400	C17—C18	1.375 (2)
C9—H9	0.9400	C17—H17	0.9400
O2—C10	1.424 (2)	C18—H18	0.9400
C10—H10A	0.9700	O5—H5	0.8300
C10—H10B	0.9700
O1—C1—C2	118.90 (17)	H10B—C10—H10C	109.5
O1—C1—C2	118.90 (17)	C6—O3—C11	114.41 (13)
O1—C1—C13	118.98 (17)	O3—C11—H11A	109.5
O1—C1—C13	118.98 (17)	O3—C11—H11B	109.5
C2—C1—C13	122.12 (16)	H11A—C11—H11B	109.5
C3—C2—C1	119.70 (17)	O3—C11—H11C	109.5
C3—C2—H2	120.2	H11A—C11—H11C	109.5
C1—C2—H2	120.2	H11B—C11—H11C	109.5
C2—C3—C4	128.64 (17)	C7—O4—C12	117.62 (13)
C2—C3—H3	115.7	O4—C12—H12A	109.5
C4—C3—H3	115.7	O4—C12—H12B	109.5
C9—C4—C5	117.57 (16)	H12A—C12—H12B	109.5
C9—C4—C3	122.92 (15)	O4—C12—H12C	109.5
C5—C4—C3	119.47 (16)	H12A—C12—H12C	109.5
O2—C5—C6	121.26 (15)	H12B—C12—H12C	109.5
O2—C5—C4	117.64 (15)	C18—C13—C14	117.93 (16)
C6—C5—C4	120.89 (15)	C18—C13—C1	122.82 (16)
O3—C6—C5	121.40 (15)	C14—C13—C1	119.25 (16)
O3—C6—C7	118.78 (15)	O5—C14—C15	117.28 (17)
C5—C6—C7	119.80 (15)	O5—C14—C13	122.11 (16)
O4—C7—C8	124.65 (16)	C15—C14—C13	120.61 (17)
O4—C7—C6	115.41 (14)	C16—C15—C14	118.20 (18)
C8—C7—C6	119.93 (16)	C16—C15—H15	120.9
C9—C8—C7	119.58 (17)	C14—C15—H15	120.9
C9—C8—H8	120.2	F1—C16—C15	118.06 (18)
C7—C8—H8	120.2	F1—C16—C17	118.05 (19)
C8—C9—C4	122.19 (16)	C15—C16—C17	123.89 (17)
C8—C9—H9	118.9	C16—C17—C18	117.68 (18)
C4—C9—H9	118.9	C16—C17—H17	121.2
C5—O2—C10	118.67 (14)	C18—C17—H17	121.2
O2—C10—H10A	109.5	C17—C18—C13	121.66 (18)
O2—C10—H10B	109.5	C17—C18—H18	119.2
H10A—C10—H10B	109.5	C13—C18—H18	119.2
O2—C10—H10C	109.5	C14—O5—H5	109.5
H10A—C10—H10C	109.5
O1—O1—C1—C2	0.0 (2)	C6—C5—O2—C10	61.3 (2)
O1—O1—C1—C13	0.0 (3)	C4—C5—O2—C10	−123.86 (17)
O1—C1—C2—C3	1.2 (3)	C5—C6—O3—C11	86.36 (19)
O1—C1—C2—C3	1.2 (3)	C7—C6—O3—C11	−95.34 (19)
C13—C1—C2—C3	−178.72 (16)	C8—C7—O4—C12	−1.9 (2)
C1—C2—C3—C4	−176.61 (17)	C6—C7—O4—C12	177.06 (15)
C2—C3—C4—C9	3.0 (3)	O1—C1—C13—C18	−174.58 (19)
C2—C3—C4—C5	−179.42 (17)	O1—C1—C13—C18	−174.58 (19)
C9—C4—C5—O2	−172.57 (15)	C2—C1—C13—C18	5.3 (3)
C3—C4—C5—O2	9.7 (2)	O1—C1—C13—C14	4.9 (3)
C9—C4—C5—C6	2.3 (2)	O1—C1—C13—C14	4.9 (3)
C3—C4—C5—C6	−175.44 (15)	C2—C1—C13—C14	−175.23 (16)
O2—C5—C6—O3	−8.1 (2)	C18—C13—C14—O5	−179.35 (16)
C4—C5—C6—O3	177.25 (14)	C1—C13—C14—O5	1.1 (3)
O2—C5—C6—C7	173.64 (15)	C18—C13—C14—C15	0.5 (3)
C4—C5—C6—C7	−1.0 (2)	C1—C13—C14—C15	−178.97 (16)
O3—C6—C7—O4	1.9 (2)	O5—C14—C15—C16	−179.04 (17)
C5—C6—C7—O4	−179.78 (14)	C13—C14—C15—C16	1.1 (3)
O3—C6—C7—C8	−179.05 (15)	C14—C15—C16—F1	178.23 (16)
C5—C6—C7—C8	−0.7 (2)	C14—C15—C16—C17	−1.7 (3)
O4—C7—C8—C9	−179.89 (16)	F1—C16—C17—C18	−179.28 (16)
C6—C7—C8—C9	1.1 (3)	C15—C16—C17—C18	0.7 (3)
C7—C8—C9—C4	0.2 (3)	C16—C17—C18—C13	1.0 (3)
C5—C4—C9—C8	−1.9 (3)	C14—C13—C18—C17	−1.6 (3)
C3—C4—C9—C8	175.76 (17)	C1—C13—C18—C17	177.87 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O1	0.83	1.77	2.499 (2)	146
C18—H18···O5^i	0.94	2.52	3.279 (2)	138

Symmetry code: (i) x, −y+1/2, z−1/2.