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

The title compound, C₁₈H₁₈O₅, was prepared by the condensation of 2-hydroxyacetophenone with 3,4,5-trimeth­oxy­benzaldehyde. The trimethoxyphenyl and hydroxy­phen­yl rings of the chalcone system are approximately coplanar.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.040
• wR factor = 0.035
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         33 Perc.
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O4     -   C17     ..       8.58 su

Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.799
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O4     -   C13     ..       6.58 su

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   3 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
   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I)

Crystal data

C18H18O5	Dx = 1.307 Mg m^−3
Mr = 314.32	Melting point = 419–421 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.686 (2) Å	Cell parameters from 33 reflections
b = 8.588 (1) Å	θ = 3.0–14.5°
c = 15.422 (3) Å	µ = 0.10 mm^−1
β = 108.00 (1)°	T = 296 K
V = 1598.1 (5) Å^3	Block, yellow
Z = 4	0.35 × 0.30 × 0.16 mm
F(000) = 664

Data collection

Siemens P4 diffractometer	Rint = 0.030
Radiation source: normal-focus sealed tube	θmax = 25.5°, θmin = 1.7°
Graphite monochromator	h = 0→15
ω scans	k = 0→10
3470 measured reflections	l = −18→17
2989 independent reflections	3 standard reflections every 97 reflections
984 reflections with I > 2σ(I)	intensity decay: 1.9%

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.035	w = 1/[σ^2(Fo^2) + (0.001P)^2 + 0.075P] where P = (Fo^2 + 2Fc^2)/3
S = 0.80	(Δ/σ)max = 0.001
2989 reflections	Δρmax = 0.16 e Å^−3
216 parameters	Δρmin = −0.12 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0061 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.01863 (19)	0.1893 (3)	0.59756 (16)	0.0805 (7)
O2	0.05501 (16)	0.3046 (2)	0.47742 (12)	0.0778 (7)
O3	0.30779 (14)	0.6528 (2)	0.15581 (11)	0.0678 (6)
O4	0.47990 (16)	0.8047 (2)	0.26095 (12)	0.0716 (6)
O5	0.52976 (16)	0.8113 (2)	0.44286 (12)	0.0792 (7)
C1	0.0472 (2)	0.2919 (4)	0.65607 (19)	0.0565 (9)
C2	0.0438 (2)	0.2930 (3)	0.74471 (19)	0.0613 (9)
H2	−0.0025	0.2242	0.7622	0.074*
C3	0.1088 (2)	0.3955 (3)	0.80710 (18)	0.0645 (9)
H3	0.1053	0.3964	0.8665	0.077*
C4	0.1789 (2)	0.4971 (3)	0.78271 (17)	0.0637 (9)
H4	0.2225	0.5663	0.8253	0.076*
C5	0.1839 (2)	0.4952 (3)	0.69457 (17)	0.0568 (9)
H5	0.2313	0.5638	0.6783	0.068*
C6	0.1191 (2)	0.3922 (3)	0.62899 (17)	0.0485 (8)
C7	0.1210 (2)	0.3888 (3)	0.53413 (19)	0.0560 (9)
C8	0.2026 (2)	0.4832 (3)	0.50757 (16)	0.0591 (9)
H8	0.2579	0.5356	0.5519	0.071*
C9	0.1978 (2)	0.4940 (3)	0.42084 (16)	0.0602 (9)
H9	0.1391	0.4425	0.3793	0.072*
C10	0.2739 (2)	0.5772 (3)	0.38231 (18)	0.0512 (8)
C11	0.2522 (2)	0.5724 (3)	0.28737 (17)	0.0555 (9)
H11	0.1907	0.5186	0.2512	0.067*
C12	0.3220 (2)	0.6476 (3)	0.24726 (18)	0.0523 (8)
C13	0.4136 (2)	0.7259 (3)	0.30183 (19)	0.0549 (9)
C14	0.4369 (2)	0.7304 (3)	0.39599 (19)	0.0563 (9)
C15	0.3663 (2)	0.6568 (3)	0.43638 (16)	0.0572 (9)
H15	0.3808	0.6609	0.4993	0.069*
C16	0.2172 (2)	0.5705 (3)	0.09724 (15)	0.0954 (12)
H16A	0.2253	0.4614	0.1114	0.114*
H16B	0.2151	0.5864	0.0351	0.114*
H16C	0.1495	0.6078	0.1054	0.114*
C17	0.58116 (19)	0.7277 (3)	0.26983 (17)	0.0900 (12)
H17A	0.6247	0.7243	0.3330	0.108*
H17B	0.6211	0.7829	0.2358	0.108*
H17C	0.5664	0.6234	0.2467	0.108*
C18	0.5601 (2)	0.8097 (3)	0.53988 (16)	0.0923 (11)
H18A	0.5024	0.8573	0.5589	0.111*
H18B	0.6278	0.8667	0.5648	0.111*
H18C	0.5704	0.7041	0.5613	0.111*
H1O	−0.015 (3)	0.204 (3)	0.5453 (10)	0.136 (17)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0838 (18)	0.0872 (19)	0.0681 (16)	−0.0336 (13)	0.0198 (14)	−0.0072 (16)
O2	0.0913 (18)	0.0822 (17)	0.0621 (14)	−0.0291 (14)	0.0269 (12)	−0.0150 (13)
O3	0.0708 (15)	0.0844 (17)	0.0452 (12)	−0.0004 (13)	0.0136 (11)	0.0067 (12)
O4	0.0640 (16)	0.0689 (16)	0.0844 (15)	0.0021 (13)	0.0265 (13)	0.0170 (13)
O5	0.0760 (17)	0.0866 (17)	0.0665 (15)	−0.0184 (14)	0.0098 (13)	−0.0083 (14)
C1	0.056 (2)	0.060 (2)	0.052 (2)	0.0011 (19)	0.0148 (18)	0.002 (2)
C2	0.062 (2)	0.063 (2)	0.061 (2)	−0.0042 (19)	0.0221 (18)	0.0108 (19)
C3	0.074 (3)	0.065 (3)	0.058 (2)	0.010 (2)	0.026 (2)	0.0100 (19)
C4	0.075 (3)	0.063 (2)	0.054 (2)	−0.0053 (19)	0.0203 (18)	0.0011 (19)
C5	0.058 (2)	0.051 (2)	0.062 (2)	−0.0022 (18)	0.0203 (18)	0.0047 (19)
C6	0.051 (2)	0.043 (2)	0.052 (2)	0.0010 (17)	0.0158 (17)	0.0016 (17)
C7	0.059 (2)	0.052 (2)	0.061 (2)	0.0021 (19)	0.0240 (19)	0.0042 (19)
C8	0.064 (2)	0.064 (2)	0.051 (2)	0.0007 (19)	0.0196 (18)	0.0009 (18)
C9	0.056 (2)	0.064 (2)	0.058 (2)	−0.0018 (18)	0.0145 (17)	0.0023 (19)
C10	0.052 (2)	0.052 (2)	0.052 (2)	0.0108 (18)	0.0205 (18)	0.0031 (17)
C11	0.056 (2)	0.054 (2)	0.054 (2)	−0.0041 (17)	0.0137 (17)	−0.0031 (17)
C12	0.054 (2)	0.049 (2)	0.050 (2)	0.0065 (18)	0.0112 (18)	0.0060 (18)
C13	0.053 (2)	0.054 (2)	0.062 (2)	0.0038 (18)	0.0254 (18)	0.0141 (19)
C14	0.060 (2)	0.050 (2)	0.056 (2)	0.0028 (18)	0.0140 (18)	0.0017 (18)
C15	0.060 (2)	0.060 (2)	0.0474 (19)	0.0048 (19)	0.0111 (18)	0.0008 (18)
C16	0.107 (3)	0.118 (3)	0.046 (2)	−0.008 (3)	0.001 (2)	0.005 (2)
C17	0.077 (3)	0.102 (3)	0.104 (3)	−0.022 (2)	0.047 (2)	−0.002 (2)
C18	0.094 (3)	0.092 (3)	0.072 (2)	−0.016 (2)	−0.002 (2)	−0.018 (2)

Geometric parameters (Å, º)

O1—C1	1.350 (3)	C8—C9	1.323 (2)
O1—H1O	0.832 (10)	C8—H8	0.9300
O2—C7	1.239 (3)	C9—C10	1.466 (3)
O3—C12	1.366 (3)	C9—H9	0.9300
O3—C16	1.412 (2)	C10—C15	1.391 (3)
O4—C13	1.375 (3)	C10—C11	1.404 (3)
O4—C17	1.413 (2)	C11—C12	1.386 (3)
O5—C14	1.366 (3)	C11—H11	0.9300
O5—C18	1.425 (2)	C12—C13	1.381 (3)
C1—C2	1.381 (3)	C13—C14	1.390 (3)
C1—C6	1.408 (3)	C14—C15	1.391 (3)
C2—C3	1.375 (3)	C15—H15	0.9300
C2—H2	0.9300	C16—H16A	0.9600
C3—C4	1.379 (3)	C16—H16B	0.9600
C3—H3	0.9300	C16—H16C	0.9600
C4—C5	1.380 (3)	C17—H17A	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C5—C6	1.402 (3)	C17—H17C	0.9600
C5—H5	0.9300	C18—H18A	0.9600
C6—C7	1.471 (3)	C18—H18B	0.9600
C7—C8	1.470 (3)	C18—H18C	0.9600
C1—O1—H1O	110 (2)	C12—C11—C10	120.4 (3)
C12—O3—C16	117.7 (2)	C12—C11—H11	119.8
C13—O4—C17	113.1 (2)	C10—C11—H11	119.8
C14—O5—C18	117.3 (2)	O3—C12—C13	115.5 (3)
O1—C1—C2	117.6 (3)	O3—C12—C11	125.3 (3)
O1—C1—C6	121.6 (3)	C13—C12—C11	119.2 (3)
C2—C1—C6	120.7 (3)	O4—C13—C12	118.6 (3)
C3—C2—C1	120.1 (3)	O4—C13—C14	120.2 (3)
C3—C2—H2	119.9	C12—C13—C14	121.2 (3)
C1—C2—H2	119.9	O5—C14—C13	115.9 (3)
C2—C3—C4	120.8 (3)	O5—C14—C15	124.3 (3)
C2—C3—H3	119.6	C13—C14—C15	119.8 (3)
C4—C3—H3	119.6	C14—C15—C10	119.7 (3)
C3—C4—C5	119.4 (3)	C14—C15—H15	120.2
C3—C4—H4	120.3	C10—C15—H15	120.2
C5—C4—H4	120.3	O3—C16—H16A	109.5
C4—C5—C6	121.5 (3)	O3—C16—H16B	109.5
C4—C5—H5	119.2	H16A—C16—H16B	109.5
C6—C5—H5	119.2	O3—C16—H16C	109.5
C5—C6—C1	117.4 (3)	H16A—C16—H16C	109.5
C5—C6—C7	122.9 (3)	H16B—C16—H16C	109.5
C1—C6—C7	119.6 (3)	O4—C17—H17A	109.5
O2—C7—C8	120.4 (3)	O4—C17—H17B	109.5
O2—C7—C6	119.9 (3)	H17A—C17—H17B	109.5
C8—C7—C6	119.7 (3)	O4—C17—H17C	109.5
C9—C8—C7	120.2 (3)	H17A—C17—H17C	109.5
C9—C8—H8	119.9	H17B—C17—H17C	109.5
C7—C8—H8	119.9	O5—C18—H18A	109.5
C8—C9—C10	127.8 (3)	O5—C18—H18B	109.5
C8—C9—H9	116.1	H18A—C18—H18B	109.5
C10—C9—H9	116.1	O5—C18—H18C	109.5
C15—C10—C11	119.8 (3)	H18A—C18—H18C	109.5
C15—C10—C9	122.4 (3)	H18B—C18—H18C	109.5
C11—C10—C9	117.9 (3)
O1—C1—C2—C3	−179.7 (3)	C9—C10—C11—C12	−179.3 (2)
C6—C1—C2—C3	1.8 (4)	C16—O3—C12—C13	178.1 (2)
C1—C2—C3—C4	−0.8 (5)	C16—O3—C12—C11	−2.5 (4)
C2—C3—C4—C5	−0.1 (4)	C10—C11—C12—O3	−178.8 (2)
C3—C4—C5—C6	0.0 (4)	C10—C11—C12—C13	0.6 (4)
C4—C5—C6—C1	0.9 (4)	C17—O4—C13—C12	−105.2 (3)
C4—C5—C6—C7	179.0 (3)	C17—O4—C13—C14	77.0 (3)
O1—C1—C6—C5	179.7 (3)	O3—C12—C13—O4	1.8 (4)
C2—C1—C6—C5	−1.8 (4)	C11—C12—C13—O4	−177.7 (2)
O1—C1—C6—C7	1.6 (4)	O3—C12—C13—C14	179.5 (2)
C2—C1—C6—C7	−179.9 (3)	C11—C12—C13—C14	0.1 (4)
C5—C6—C7—O2	−173.8 (3)	C18—O5—C14—C13	−176.0 (2)
C1—C6—C7—O2	4.2 (4)	C18—O5—C14—C15	4.9 (4)
C5—C6—C7—C8	7.3 (4)	O4—C13—C14—O5	−2.3 (4)
C1—C6—C7—C8	−174.7 (3)	C12—C13—C14—O5	180.0 (3)
O2—C7—C8—C9	8.2 (4)	O4—C13—C14—C15	176.8 (3)
C6—C7—C8—C9	−172.9 (3)	C12—C13—C14—C15	−0.9 (4)
C7—C8—C9—C10	−177.5 (3)	O5—C14—C15—C10	−179.9 (2)
C8—C9—C10—C15	1.1 (4)	C13—C14—C15—C10	1.1 (4)
C8—C9—C10—C11	180.0 (3)	C11—C10—C15—C14	−0.4 (4)
C15—C10—C11—C12	−0.4 (4)	C9—C10—C15—C14	178.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2	0.83 (1)	1.79 (2)	2.521 (3)	146 (3)