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

In the title chalcone derivative, C₁₉H₂₀O₅, the dihedral angle between the planes of the benzene rings is 3.97 (8)°. In the monosubstituted ring, the meth­oxy C atom is almost coplanar with the ring [deviation = 0.016 (3) Å]. In the tris­ubstituted ring, the C atoms of the ortho, meta and para meth­oxy sustituents deviate by −0.030 (2), 1.127 (2) and −0.052 (2) Å, respectively. In the crystal, mol­ecules are linked by weak C—H...O hydrogen bonds, forming C(9) chains propagating along [010].

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.052
• wR factor = 0.172
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5841
PLAT023_ALERT_3_C Resolution (too) Low [sin(theta)/Lambda < 0.6]..      64.23 Degree
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.968 Note
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.584         87 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         11 Note

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.12 Report
PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as      mixed Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          85 % Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Note

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   7 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: ... All the authors have equal contributions to this work. VMS -- Synthesis NS -- Data collection DKA -- Spectoscopic studies AKK -- Designed the synthesis NKL -- Final analysis, write up VM -- Solved and analyzed the structure HRM -- Data processing and Corresponding Author

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Mercury (Macrae et al., 2008).

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

Crystal data

C19H20O5	Z = 2
Mr = 328.35	F(000) = 348
Triclinic, P1	Dx = 1.311 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 8.4043 (5) Å	Cell parameters from 2528 reflections
b = 8.5518 (5) Å	θ = 5.7–64.2°
c = 12.9352 (7) Å	µ = 0.78 mm^−1
α = 75.400 (2)°	T = 296 K
β = 88.427 (2)°	Prism, yellow
γ = 68.014 (2)°	0.29 × 0.26 × 0.22 mm
V = 831.91 (8) Å^3

Data collection

Bruker X8 Proteum diffractometer	2684 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2528 reflections with I > 2σ(I)
Helios multilayer optics monochromator	Rint = 0.038
Detector resolution: 18.4 pixels mm^-1	θmax = 64.2°, θmin = 5.7°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −9→9
Tmin = 0.806, Tmax = 0.847	l = −15→15
7500 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.1152P)^2 + 0.1101P] where P = (Fo^2 + 2Fc^2)/3
2684 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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	−0.08544 (15)	0.66789 (16)	0.33941 (9)	0.0568 (4)
O2	−0.14008 (16)	1.00180 (16)	0.23295 (10)	0.0602 (4)
O3	0.30064 (17)	0.99036 (16)	0.47183 (10)	0.0619 (4)
O4	0.57780 (19)	0.52820 (17)	0.76489 (11)	0.0733 (5)
O5	0.7804 (2)	−0.26807 (16)	0.98697 (11)	0.0752 (5)
C1	0.23192 (19)	0.7438 (2)	0.48953 (12)	0.0424 (5)
C2	0.1357 (2)	0.6634 (2)	0.45203 (12)	0.0448 (5)
C3	0.0145 (2)	0.7502 (2)	0.36718 (12)	0.0458 (5)
C4	−0.0154 (2)	0.9247 (2)	0.31510 (12)	0.0463 (5)
C5	0.0797 (2)	1.0066 (2)	0.34882 (12)	0.0475 (5)
C6	0.20205 (19)	0.9174 (2)	0.43478 (12)	0.0441 (5)
C7	−0.0424 (3)	0.6121 (3)	0.24368 (16)	0.0684 (7)
C8	−0.1753 (2)	1.1788 (2)	0.17818 (14)	0.0592 (5)
C9	0.2730 (2)	1.1681 (2)	0.42455 (16)	0.0605 (6)
C10	0.3533 (2)	0.6570 (2)	0.58348 (12)	0.0461 (5)
C11	0.4058 (2)	0.4919 (2)	0.64046 (12)	0.0479 (5)
C12	0.5255 (2)	0.4286 (2)	0.73643 (13)	0.0486 (5)
C13	0.58235 (19)	0.2432 (2)	0.79999 (12)	0.0449 (5)
C14	0.7088 (2)	0.1848 (2)	0.88415 (13)	0.0527 (5)
C15	0.7692 (2)	0.0159 (2)	0.94495 (14)	0.0575 (6)
C16	0.7061 (2)	−0.1025 (2)	0.92435 (12)	0.0516 (5)
C17	0.5784 (2)	−0.0474 (2)	0.84262 (13)	0.0522 (6)
C18	0.5185 (2)	0.1237 (2)	0.78175 (13)	0.0496 (5)
C19	0.7183 (4)	−0.3948 (3)	0.9746 (2)	0.0885 (9)
H2	0.15480	0.54760	0.48580	0.0540*
H5	0.06150	1.12180	0.31380	0.0570*
H7A	−0.07100	0.71240	0.18330	0.1030*
H7B	−0.10590	0.54270	0.23520	0.1030*
H7C	0.07870	0.54360	0.24820	0.1030*
H8A	−0.20830	1.24950	0.22810	0.0890*
H8B	−0.26730	1.21820	0.12380	0.0890*
H8C	−0.07420	1.18830	0.14560	0.0890*
H9A	0.29970	1.18270	0.35100	0.0910*
H9B	0.34580	1.20220	0.46240	0.0910*
H9C	0.15480	1.23980	0.42830	0.0910*
H10	0.40020	0.72630	0.60660	0.0550*
H11	0.36660	0.41540	0.61960	0.0580*
H14	0.75260	0.26260	0.89890	0.0630*
H15	0.85320	−0.02000	1.00060	0.0690*
H17	0.53350	−0.12510	0.82900	0.0630*
H18	0.43300	0.16000	0.72700	0.0600*
H19A	0.60300	−0.36600	0.99660	0.1330*
H19B	0.79080	−0.50750	1.01810	0.1330*
H19C	0.71880	−0.39730	0.90080	0.1330*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0634 (8)	0.0655 (8)	0.0504 (7)	−0.0392 (6)	−0.0064 (5)	−0.0066 (5)
O2	0.0617 (8)	0.0535 (7)	0.0564 (7)	−0.0224 (6)	−0.0212 (5)	0.0045 (5)
O3	0.0686 (8)	0.0508 (7)	0.0689 (8)	−0.0324 (6)	−0.0183 (6)	−0.0028 (6)
O4	0.0887 (10)	0.0541 (8)	0.0762 (9)	−0.0311 (7)	−0.0355 (7)	−0.0048 (6)
O5	0.1034 (11)	0.0482 (7)	0.0655 (8)	−0.0280 (7)	−0.0345 (7)	0.0026 (6)
C1	0.0417 (8)	0.0441 (8)	0.0406 (8)	−0.0176 (6)	0.0007 (6)	−0.0074 (6)
C2	0.0485 (9)	0.0418 (8)	0.0424 (8)	−0.0196 (7)	−0.0011 (6)	−0.0036 (6)
C3	0.0480 (8)	0.0505 (9)	0.0422 (8)	−0.0253 (7)	−0.0006 (6)	−0.0073 (6)
C4	0.0445 (8)	0.0490 (9)	0.0412 (8)	−0.0174 (7)	−0.0035 (6)	−0.0046 (6)
C5	0.0514 (9)	0.0397 (8)	0.0469 (9)	−0.0175 (7)	−0.0014 (7)	−0.0028 (6)
C6	0.0435 (8)	0.0448 (8)	0.0468 (8)	−0.0204 (6)	0.0011 (6)	−0.0108 (6)
C7	0.0832 (13)	0.0698 (12)	0.0652 (11)	−0.0409 (10)	−0.0045 (9)	−0.0204 (9)
C8	0.0616 (10)	0.0489 (9)	0.0525 (9)	−0.0116 (8)	−0.0111 (7)	−0.0013 (7)
C9	0.0685 (11)	0.0506 (10)	0.0702 (11)	−0.0325 (8)	0.0001 (8)	−0.0135 (8)
C10	0.0446 (8)	0.0499 (9)	0.0450 (8)	−0.0205 (7)	−0.0018 (6)	−0.0101 (7)
C11	0.0505 (9)	0.0476 (9)	0.0448 (8)	−0.0185 (7)	−0.0068 (6)	−0.0096 (7)
C12	0.0488 (9)	0.0488 (9)	0.0484 (9)	−0.0188 (7)	−0.0055 (7)	−0.0119 (7)
C13	0.0418 (8)	0.0498 (9)	0.0413 (8)	−0.0155 (7)	−0.0029 (6)	−0.0109 (7)
C14	0.0577 (10)	0.0512 (9)	0.0508 (9)	−0.0228 (8)	−0.0114 (7)	−0.0114 (7)
C15	0.0632 (11)	0.0549 (10)	0.0501 (9)	−0.0203 (8)	−0.0210 (7)	−0.0069 (7)
C16	0.0601 (10)	0.0478 (9)	0.0421 (8)	−0.0181 (7)	−0.0066 (7)	−0.0062 (6)
C17	0.0568 (10)	0.0545 (10)	0.0492 (9)	−0.0272 (8)	−0.0053 (7)	−0.0101 (7)
C18	0.0471 (9)	0.0542 (9)	0.0458 (8)	−0.0202 (7)	−0.0094 (6)	−0.0071 (7)
C19	0.129 (2)	0.0526 (11)	0.0811 (14)	−0.0407 (12)	−0.0277 (13)	0.0008 (10)

Geometric parameters (Å, º)

O1—C3	1.384 (2)	C16—C17	1.387 (2)
O1—C7	1.427 (2)	C17—C18	1.380 (2)
O2—C4	1.361 (2)	C2—H2	0.9300
O2—C8	1.420 (2)	C5—H5	0.9300
O3—C6	1.366 (2)	C7—H7A	0.9600
O3—C9	1.419 (2)	C7—H7B	0.9600
O4—C12	1.225 (2)	C7—H7C	0.9600
O5—C16	1.356 (2)	C8—H8A	0.9600
O5—C19	1.410 (3)	C8—H8B	0.9600
C1—C2	1.403 (2)	C8—H8C	0.9600
C1—C6	1.403 (2)	C9—H9A	0.9600
C1—C10	1.454 (2)	C9—H9B	0.9600
C2—C3	1.370 (2)	C9—H9C	0.9600
C3—C4	1.402 (2)	C10—H10	0.9300
C4—C5	1.383 (2)	C11—H11	0.9300
C5—C6	1.387 (2)	C14—H14	0.9300
C10—C11	1.326 (2)	C15—H15	0.9300
C11—C12	1.473 (2)	C17—H17	0.9300
C12—C13	1.488 (2)	C18—H18	0.9300
C13—C14	1.399 (2)	C19—H19A	0.9600
C13—C18	1.388 (2)	C19—H19B	0.9600
C14—C15	1.365 (2)	C19—H19C	0.9600
C15—C16	1.387 (2)
C3—O1—C7	114.51 (15)	O1—C7—H7A	109.00
C4—O2—C8	117.75 (14)	O1—C7—H7B	109.00
C6—O3—C9	119.38 (14)	O1—C7—H7C	109.00
C16—O5—C19	118.90 (17)	H7A—C7—H7B	110.00
C2—C1—C6	117.17 (14)	H7A—C7—H7C	109.00
C2—C1—C10	122.71 (15)	H7B—C7—H7C	109.00
C6—C1—C10	120.08 (15)	O2—C8—H8A	109.00
C1—C2—C3	122.07 (15)	O2—C8—H8B	109.00
O1—C3—C2	119.19 (14)	O2—C8—H8C	109.00
O1—C3—C4	120.94 (15)	H8A—C8—H8B	109.00
C2—C3—C4	119.69 (16)	H8A—C8—H8C	110.00
O2—C4—C3	115.81 (15)	H8B—C8—H8C	109.00
O2—C4—C5	124.56 (15)	O3—C9—H9A	110.00
C3—C4—C5	119.63 (15)	O3—C9—H9B	109.00
C4—C5—C6	120.15 (15)	O3—C9—H9C	110.00
O3—C6—C1	115.64 (14)	H9A—C9—H9B	109.00
O3—C6—C5	123.09 (15)	H9A—C9—H9C	109.00
C1—C6—C5	121.27 (15)	H9B—C9—H9C	109.00
C1—C10—C11	128.37 (16)	C1—C10—H10	116.00
C10—C11—C12	120.64 (15)	C11—C10—H10	116.00
O4—C12—C11	120.34 (15)	C10—C11—H11	120.00
O4—C12—C13	119.65 (15)	C12—C11—H11	120.00
C11—C12—C13	120.01 (15)	C13—C14—H14	119.00
C12—C13—C14	117.90 (15)	C15—C14—H14	119.00
C12—C13—C18	124.59 (15)	C14—C15—H15	120.00
C14—C13—C18	117.51 (15)	C16—C15—H15	120.00
C13—C14—C15	121.25 (16)	C16—C17—H17	120.00
C14—C15—C16	120.45 (16)	C18—C17—H17	120.00
O5—C16—C15	115.28 (15)	C13—C18—H18	119.00
O5—C16—C17	125.16 (16)	C17—C18—H18	119.00
C15—C16—C17	119.54 (15)	O5—C19—H19A	109.00
C16—C17—C18	119.41 (16)	O5—C19—H19B	109.00
C13—C18—C17	121.83 (16)	O5—C19—H19C	109.00
C1—C2—H2	119.00	H19A—C19—H19B	109.00
C3—C2—H2	119.00	H19A—C19—H19C	110.00
C4—C5—H5	120.00	H19B—C19—H19C	109.00
C6—C5—H5	120.00
C7—O1—C3—C2	−106.74 (18)	O2—C4—C5—C6	178.85 (16)
C7—O1—C3—C4	78.1 (2)	C3—C4—C5—C6	−1.0 (2)
C8—O2—C4—C3	179.72 (14)	C4—C5—C6—O3	179.76 (15)
C8—O2—C4—C5	−0.2 (2)	C4—C5—C6—C1	−0.2 (2)
C9—O3—C6—C1	−176.91 (15)	C1—C10—C11—C12	−177.62 (16)
C9—O3—C6—C5	3.1 (2)	C10—C11—C12—O4	0.1 (3)
C19—O5—C16—C15	177.11 (19)	C10—C11—C12—C13	179.59 (16)
C19—O5—C16—C17	−4.3 (3)	O4—C12—C13—C14	−6.7 (2)
C6—C1—C2—C3	−1.4 (2)	O4—C12—C13—C18	173.22 (17)
C10—C1—C2—C3	176.10 (16)	C11—C12—C13—C14	173.85 (15)
C2—C1—C6—O3	−178.56 (14)	C11—C12—C13—C18	−6.2 (3)
C2—C1—C6—C5	1.4 (2)	C12—C13—C14—C15	−179.02 (16)
C10—C1—C6—O3	3.8 (2)	C18—C13—C14—C15	1.1 (3)
C10—C1—C6—C5	−176.17 (15)	C12—C13—C18—C17	179.03 (16)
C2—C1—C10—C11	7.4 (3)	C14—C13—C18—C17	−1.1 (3)
C6—C1—C10—C11	−175.12 (17)	C13—C14—C15—C16	0.1 (3)
C1—C2—C3—O1	−174.99 (15)	C14—C15—C16—O5	177.44 (16)
C1—C2—C3—C4	0.2 (3)	C14—C15—C16—C17	−1.2 (3)
O1—C3—C4—O2	−3.7 (2)	O5—C16—C17—C18	−177.30 (16)
O1—C3—C4—C5	176.17 (15)	C15—C16—C17—C18	1.2 (3)
C2—C3—C4—O2	−178.85 (15)	C16—C17—C18—C13	−0.1 (3)
C2—C3—C4—C5	1.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19C···O4^i	0.96	2.48	3.293 (3)	143

Symmetry code: (i) x, y−1, z.