Crystal structure of (E)-3-(2-hy­droxy-4-methyl­phen­yl)-1-(2,4,6-tri­meth­oxy­phen­yl)prop-2-en-1-one

The title compound consists of a 2-hy­droxy-4-methyl­phenyl ring, a 2,4,6-tri­meth­oxy­phenyl ring and a prop-2-en-1-one connecting bridge. The overall conformations of the title compound are discussed and compared with those of related structures. In the crystal, mol­ecules are consolidated by O—H...O hydrogen bonds and weak C—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.052
• wR factor = 0.171
• Data-to-parameter ratio = 23.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17A     ..O1       .       2.70 Ang.

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C19 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         35 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 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

   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   3 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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXL2013 (Sheldrick, 2015) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015) and PLATON (Spek, 2009).

(E)-3-(2-Hydroxy-4-methylphenyl)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one

Crystal data

C19H20O5	Z = 2
Mr = 328.35	F(000) = 348
Triclinic, P1	Dx = 1.275 Mg m^−3
a = 6.8072 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.5792 (4) Å	Cell parameters from 6606 reflections
c = 15.8010 (7) Å	θ = 2.5–25.7°
α = 100.365 (1)°	µ = 0.09 mm^−1
β = 99.433 (1)°	T = 296 K
γ = 104.984 (1)°	Block, brown
V = 855.09 (7) Å^3	0.57 × 0.25 × 0.21 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer	5018 independent reflections
Radiation source: fine-focus sealed tube	3199 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 30.1°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −9→9
Tmin = 0.908, Tmax = 0.950	k = −12→12
33448 measured reflections	l = −22→22

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.171	w = 1/[σ^2(Fo^2) + (0.0776P)^2 + 0.1331P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
5018 reflections	Δρmax = 0.27 e Å^−3
217 parameters	Δρmin = −0.19 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	0.64130 (18)	0.04792 (12)	0.33273 (7)	0.0582 (3)
H1B	0.622234	−0.051206	0.330607	0.087*
O2	0.5594 (2)	0.71937 (13)	0.28620 (9)	0.0750 (4)
O3	0.82818 (19)	0.58546 (15)	0.17162 (8)	0.0718 (4)
O4	0.3336 (2)	0.11733 (16)	−0.04471 (7)	0.0741 (4)
O5	0.18978 (18)	0.33623 (15)	0.22860 (8)	0.0653 (3)
C1	0.7621 (3)	0.3898 (2)	0.52362 (11)	0.0587 (4)
H1A	0.765072	0.500561	0.536913	0.070*
C2	0.8168 (3)	0.3175 (2)	0.59089 (11)	0.0636 (4)
H2A	0.856694	0.379893	0.648810	0.076*
C3	0.8134 (2)	0.1518 (2)	0.57349 (10)	0.0576 (4)
C4	0.7548 (2)	0.0621 (2)	0.48690 (10)	0.0536 (4)
H4A	0.752792	−0.048531	0.474238	0.064*
C5	0.6988 (2)	0.13422 (17)	0.41849 (9)	0.0462 (3)
C6	0.7017 (2)	0.30075 (17)	0.43524 (9)	0.0461 (3)
C7	0.6399 (2)	0.37021 (17)	0.36199 (9)	0.0462 (3)
H7A	0.600214	0.297697	0.306638	0.055*
C8	0.6322 (2)	0.52507 (17)	0.36314 (10)	0.0530 (4)
H8A	0.670606	0.601882	0.417082	0.064*
C9	0.5668 (2)	0.57758 (17)	0.28428 (10)	0.0506 (3)
C10	0.5066 (2)	0.45590 (17)	0.19626 (10)	0.0474 (3)
C11	0.3145 (2)	0.33383 (18)	0.16927 (10)	0.0496 (3)
C12	0.2590 (2)	0.2222 (2)	0.08827 (10)	0.0553 (4)
H12A	0.130137	0.141133	0.070877	0.066*
C13	0.3996 (3)	0.23348 (19)	0.03331 (10)	0.0539 (4)
C14	0.5911 (2)	0.35440 (19)	0.05781 (10)	0.0528 (4)
H14A	0.683280	0.361673	0.020255	0.063*
C15	0.6426 (2)	0.46422 (18)	0.13936 (10)	0.0502 (3)
C16	0.9764 (3)	0.6078 (3)	0.11824 (14)	0.0747 (5)
H16A	1.098130	0.697163	0.149806	0.112*
H16B	1.014327	0.507669	0.103655	0.112*
H16C	0.917128	0.633866	0.065061	0.112*
C17	0.4721 (4)	0.1217 (3)	−0.10396 (12)	0.0798 (6)
H17A	0.408006	0.034279	−0.156077	0.120*
H17B	0.501338	0.226820	−0.119882	0.120*
H17C	0.599756	0.106887	−0.075655	0.120*
C18	−0.0021 (3)	0.2085 (3)	0.21029 (14)	0.0741 (5)
H18A	−0.072792	0.225952	0.257352	0.111*
H18B	−0.087708	0.210054	0.155938	0.111*
H18C	0.024368	0.102923	0.205183	0.111*
C19	0.8715 (3)	0.0699 (3)	0.64692 (12)	0.0785 (6)
H19A	0.908022	0.148913	0.702583	0.118*
H19B	0.755129	−0.021899	0.646508	0.118*
H19C	0.988302	0.030616	0.638320	0.118*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0834 (8)	0.0397 (5)	0.0461 (6)	0.0191 (5)	0.0077 (5)	0.0007 (4)
O2	0.1156 (11)	0.0394 (6)	0.0798 (8)	0.0294 (6)	0.0388 (8)	0.0135 (5)
O3	0.0660 (7)	0.0665 (7)	0.0692 (8)	−0.0007 (6)	0.0305 (6)	−0.0029 (6)
O4	0.0803 (9)	0.0796 (8)	0.0461 (6)	0.0084 (7)	0.0123 (6)	−0.0022 (6)
O5	0.0577 (7)	0.0702 (7)	0.0659 (7)	0.0118 (5)	0.0271 (6)	0.0090 (6)
C1	0.0631 (9)	0.0534 (8)	0.0508 (8)	0.0140 (7)	0.0116 (7)	−0.0047 (7)
C2	0.0594 (9)	0.0766 (11)	0.0441 (8)	0.0141 (8)	0.0094 (7)	−0.0018 (7)
C3	0.0434 (8)	0.0790 (11)	0.0486 (8)	0.0153 (7)	0.0102 (6)	0.0146 (7)
C4	0.0527 (8)	0.0538 (8)	0.0543 (8)	0.0169 (7)	0.0119 (7)	0.0113 (7)
C5	0.0454 (7)	0.0463 (7)	0.0431 (7)	0.0118 (6)	0.0099 (6)	0.0030 (6)
C6	0.0432 (7)	0.0440 (7)	0.0464 (7)	0.0097 (5)	0.0117 (6)	0.0018 (6)
C7	0.0476 (7)	0.0406 (7)	0.0466 (7)	0.0112 (5)	0.0130 (6)	0.0009 (5)
C8	0.0607 (9)	0.0413 (7)	0.0523 (8)	0.0129 (6)	0.0163 (7)	−0.0009 (6)
C9	0.0586 (8)	0.0357 (6)	0.0600 (9)	0.0137 (6)	0.0246 (7)	0.0074 (6)
C10	0.0557 (8)	0.0403 (7)	0.0507 (8)	0.0185 (6)	0.0173 (6)	0.0108 (6)
C11	0.0525 (8)	0.0491 (8)	0.0530 (8)	0.0198 (6)	0.0169 (6)	0.0152 (6)
C12	0.0529 (8)	0.0563 (9)	0.0522 (8)	0.0117 (7)	0.0082 (7)	0.0113 (7)
C13	0.0638 (9)	0.0550 (8)	0.0426 (7)	0.0206 (7)	0.0073 (7)	0.0103 (6)
C14	0.0597 (9)	0.0568 (8)	0.0475 (8)	0.0214 (7)	0.0192 (7)	0.0136 (7)
C15	0.0539 (8)	0.0446 (7)	0.0543 (8)	0.0156 (6)	0.0169 (7)	0.0113 (6)
C16	0.0663 (11)	0.0762 (12)	0.0799 (13)	0.0099 (9)	0.0345 (10)	0.0137 (10)
C17	0.1025 (15)	0.0791 (12)	0.0497 (10)	0.0168 (11)	0.0256 (10)	0.0018 (8)
C18	0.0613 (10)	0.0826 (13)	0.0820 (13)	0.0132 (9)	0.0271 (9)	0.0297 (10)
C19	0.0684 (11)	0.1119 (16)	0.0570 (11)	0.0267 (11)	0.0087 (9)	0.0291 (10)

Geometric parameters (Å, º)

O1—C5	1.3613 (16)	C8—H8A	0.9300
O1—H1B	0.8200	C9—C10	1.504 (2)
O2—C9	1.2255 (17)	C10—C15	1.390 (2)
O3—C15	1.3626 (19)	C10—C11	1.392 (2)
O3—C16	1.4151 (19)	C11—C12	1.383 (2)
O4—C13	1.3636 (18)	C12—C13	1.391 (2)
O4—C17	1.432 (2)	C12—H12A	0.9300
O5—C11	1.3651 (18)	C13—C14	1.385 (2)
O5—C18	1.419 (2)	C14—C15	1.384 (2)
C1—C2	1.371 (2)	C14—H14A	0.9300
C1—C6	1.403 (2)	C16—H16A	0.9600
C1—H1A	0.9300	C16—H16B	0.9600
C2—C3	1.392 (3)	C16—H16C	0.9600
C2—H2A	0.9300	C17—H17A	0.9600
C3—C4	1.381 (2)	C17—H17B	0.9600
C3—C19	1.511 (2)	C17—H17C	0.9600
C4—C5	1.387 (2)	C18—H18A	0.9600
C4—H4A	0.9300	C18—H18B	0.9600
C5—C6	1.3998 (19)	C18—H18C	0.9600
C6—C7	1.446 (2)	C19—H19A	0.9600
C7—C8	1.340 (2)	C19—H19B	0.9600
C7—H7A	0.9300	C19—H19C	0.9600
C8—C9	1.441 (2)
C5—O1—H1B	109.5	C11—C12—C13	118.68 (15)
C15—O3—C16	119.21 (13)	C11—C12—H12A	120.7
C13—O4—C17	117.54 (14)	C13—C12—H12A	120.7
C11—O5—C18	118.63 (14)	O4—C13—C14	123.74 (14)
C2—C1—C6	121.65 (15)	O4—C13—C12	114.86 (14)
C2—C1—H1A	119.2	C14—C13—C12	121.39 (14)
C6—C1—H1A	119.2	C15—C14—C13	118.62 (14)
C1—C2—C3	120.75 (15)	C15—C14—H14A	120.7
C1—C2—H2A	119.6	C13—C14—H14A	120.7
C3—C2—H2A	119.6	O3—C15—C14	123.97 (13)
C4—C3—C2	118.51 (15)	O3—C15—C10	114.45 (13)
C4—C3—C19	120.07 (17)	C14—C15—C10	121.57 (14)
C2—C3—C19	121.41 (16)	O3—C16—H16A	109.5
C3—C4—C5	121.08 (15)	O3—C16—H16B	109.5
C3—C4—H4A	119.5	H16A—C16—H16B	109.5
C5—C4—H4A	119.5	O3—C16—H16C	109.5
O1—C5—C4	121.92 (13)	H16A—C16—H16C	109.5
O1—C5—C6	117.19 (12)	H16B—C16—H16C	109.5
C4—C5—C6	120.89 (13)	O4—C17—H17A	109.5
C5—C6—C1	117.12 (14)	O4—C17—H17B	109.5
C5—C6—C7	118.98 (12)	H17A—C17—H17B	109.5
C1—C6—C7	123.89 (13)	O4—C17—H17C	109.5
C8—C7—C6	128.71 (13)	H17A—C17—H17C	109.5
C8—C7—H7A	115.6	H17B—C17—H17C	109.5
C6—C7—H7A	115.6	O5—C18—H18A	109.5
C7—C8—C9	122.77 (13)	O5—C18—H18B	109.5
C7—C8—H8A	118.6	H18A—C18—H18B	109.5
C9—C8—H8A	118.6	O5—C18—H18C	109.5
O2—C9—C8	122.17 (14)	H18A—C18—H18C	109.5
O2—C9—C10	118.36 (14)	H18B—C18—H18C	109.5
C8—C9—C10	119.47 (12)	C3—C19—H19A	109.5
C15—C10—C11	118.35 (13)	C3—C19—H19B	109.5
C15—C10—C9	120.27 (13)	H19A—C19—H19B	109.5
C11—C10—C9	121.37 (13)	C3—C19—H19C	109.5
O5—C11—C12	124.18 (14)	H19A—C19—H19C	109.5
O5—C11—C10	114.43 (13)	H19B—C19—H19C	109.5
C12—C11—C10	121.39 (14)
C6—C1—C2—C3	−0.3 (3)	C18—O5—C11—C12	5.6 (2)
C1—C2—C3—C4	0.4 (2)	C18—O5—C11—C10	−174.96 (14)
C1—C2—C3—C19	−179.49 (16)	C15—C10—C11—O5	−179.09 (12)
C2—C3—C4—C5	−0.5 (2)	C9—C10—C11—O5	0.4 (2)
C19—C3—C4—C5	179.37 (14)	C15—C10—C11—C12	0.4 (2)
C3—C4—C5—O1	179.78 (14)	C9—C10—C11—C12	179.85 (13)
C3—C4—C5—C6	0.5 (2)	O5—C11—C12—C13	179.48 (13)
O1—C5—C6—C1	−179.66 (13)	C10—C11—C12—C13	0.1 (2)
C4—C5—C6—C1	−0.3 (2)	C17—O4—C13—C14	0.2 (2)
O1—C5—C6—C7	1.36 (19)	C17—O4—C13—C12	−179.57 (15)
C4—C5—C6—C7	−179.32 (13)	C11—C12—C13—O4	179.14 (13)
C2—C1—C6—C5	0.2 (2)	C11—C12—C13—C14	−0.6 (2)
C2—C1—C6—C7	179.15 (14)	O4—C13—C14—C15	−178.99 (14)
C5—C6—C7—C8	−179.68 (14)	C12—C13—C14—C15	0.8 (2)
C1—C6—C7—C8	1.4 (2)	C16—O3—C15—C14	3.0 (2)
C6—C7—C8—C9	−179.96 (14)	C16—O3—C15—C10	−178.38 (15)
C7—C8—C9—O2	179.67 (15)	C13—C14—C15—O3	178.26 (14)
C7—C8—C9—C10	−0.8 (2)	C13—C14—C15—C10	−0.3 (2)
O2—C9—C10—C15	75.90 (19)	C11—C10—C15—O3	−178.96 (13)
C8—C9—C10—C15	−103.68 (16)	C9—C10—C15—O3	1.6 (2)
O2—C9—C10—C11	−103.56 (17)	C11—C10—C15—C14	−0.3 (2)
C8—C9—C10—C11	76.87 (19)	C9—C10—C15—C14	−179.73 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O2^i	0.82	1.88	2.6653 (15)	161
C17—H17A···O1^ii	0.96	2.70	3.520 (2)	144

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