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

The mol­ecule of the title compound C₁₉H₁₈O₆, adopts an E conformation about the C=C double bond and the C—C=C—C torsion angle is −179.30 (16)°. The mol­ecule is nearly planar, as indicated by the dihedral angle of 6.99 (6)° between the benzene ring and the benzodioxalane ring. In the crystal, mol­ecules are linked via weak C—H...O hydrogen bonds, forming zigzag chains propagating along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.046
• wR factor = 0.145
• Data-to-parameter ratio = 11.2

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 =    0.5856
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.978 Note
PLAT397_ALERT_2_C Deviating  C-O-C  Angle from 120 Deg for  O5          105.9 Degree
PLAT397_ALERT_2_C Deviating  C-O-C  Angle from 120 Deg for  O6          106.3 Degree
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.586         58 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 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       0.11 Report
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          74 % Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 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 and Corresponding Author 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, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); 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-(1,3-Benzodioxol-5-yl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one

Crystal data

C19H18O6	F(000) = 720
Mr = 342.33	Dx = 1.455 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 2568 reflections
a = 10.9127 (2) Å	θ = 5.3–64.5°
b = 13.4406 (3) Å	µ = 0.91 mm^−1
c = 11.1011 (2) Å	T = 296 K
β = 106.287 (1)°	Block, yellow
V = 1562.89 (5) Å^3	0.29 × 0.26 × 0.24 mm
Z = 4

Data collection

Bruker X8 Proteum diffractometer	2568 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2283 reflections with I > 2σ(I)
Helios multilayer optics monochromator	Rint = 0.054
Detector resolution: 18.4 pixels mm^-1	θmax = 64.5°, θmin = 5.3°
φ and ω scans	h = −11→12
Absorption correction: multi-scan (SADABS; Bruker, 2011)	k = −15→15
Tmin = 0.779, Tmax = 0.812	l = −12→12
12593 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.145	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.1062P)^2 + 0.0554P] where P = (Fo^2 + 2Fc^2)/3
2568 reflections	(Δ/σ)max = 0.001
229 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.30 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	0.91113 (10)	1.12891 (8)	1.26097 (10)	0.0195 (3)
O2	1.03766 (10)	1.20902 (8)	1.12453 (10)	0.0211 (3)
O3	0.78978 (11)	1.03030 (9)	0.75876 (10)	0.0253 (4)
O4	0.48629 (11)	0.80424 (9)	0.74724 (10)	0.0256 (4)
O5	0.11332 (10)	0.58892 (9)	0.77554 (10)	0.0225 (3)
O6	0.11852 (11)	0.57683 (9)	0.98559 (11)	0.0239 (4)
C1	0.75134 (14)	1.00721 (11)	0.95591 (15)	0.0168 (5)
C2	0.77990 (14)	1.03224 (11)	1.08453 (14)	0.0166 (5)
C3	0.87534 (14)	1.09951 (12)	1.13825 (14)	0.0170 (5)
C4	0.94560 (14)	1.14401 (11)	1.06326 (15)	0.0173 (5)
C5	0.91856 (15)	1.12160 (11)	0.93735 (15)	0.0186 (5)
C6	0.82250 (15)	1.05351 (12)	0.88408 (14)	0.0179 (5)
C7	0.65492 (15)	0.93450 (11)	0.89609 (15)	0.0179 (5)
C8	0.57013 (15)	0.88508 (11)	0.94087 (15)	0.0184 (5)
C9	0.48403 (14)	0.81406 (12)	0.85739 (15)	0.0185 (5)
C10	0.39080 (14)	0.75351 (11)	0.90211 (14)	0.0167 (4)
C11	0.29852 (14)	0.70065 (11)	0.80904 (14)	0.0180 (5)
C12	0.21113 (14)	0.64612 (11)	0.84800 (15)	0.0174 (5)
C13	0.04917 (16)	0.54733 (12)	0.86066 (15)	0.0218 (5)
C14	0.21371 (15)	0.63905 (11)	0.97324 (15)	0.0178 (5)
C15	0.30402 (15)	0.68775 (12)	1.06610 (15)	0.0198 (5)
C16	0.39221 (15)	0.74662 (12)	1.02786 (15)	0.0183 (5)
C17	0.84472 (16)	1.08758 (13)	1.34227 (15)	0.0234 (5)
C18	1.11336 (15)	1.25347 (13)	1.05277 (15)	0.0227 (5)
C19	0.87351 (16)	1.06180 (12)	0.68832 (15)	0.0226 (5)
H2	0.73360	1.00290	1.13380	0.0200*
H5	0.96430	1.15180	0.88820	0.0220*
H7	0.65140	0.91980	0.81330	0.0220*
H8	0.56590	0.89550	1.02240	0.0220*
H11	0.29740	0.70290	0.72500	0.0210*
H13A	−0.03790	0.57170	0.84070	0.0260*
H13B	0.04680	0.47540	0.85400	0.0260*
H15	0.30640	0.68190	1.15020	0.0240*
H16	0.45330	0.78200	1.08790	0.0220*
H17A	0.75530	1.10180	1.31010	0.0350*
H17B	0.87660	1.11610	1.42440	0.0350*
H17C	0.85740	1.01680	1.34720	0.0350*
H18A	1.15250	1.20220	1.01600	0.0340*
H18B	1.17840	1.29410	1.10660	0.0340*
H18C	1.06000	1.29390	0.98760	0.0340*
H19A	0.87440	1.13320	0.68500	0.0340*
H19B	0.84450	1.03560	0.60470	0.0340*
H19C	0.95820	1.03790	0.72780	0.0340*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0220 (6)	0.0216 (6)	0.0148 (6)	−0.0055 (4)	0.0049 (5)	−0.0011 (4)
O2	0.0203 (6)	0.0225 (6)	0.0193 (6)	−0.0070 (4)	0.0035 (5)	−0.0002 (4)
O3	0.0311 (7)	0.0300 (7)	0.0164 (6)	−0.0111 (5)	0.0094 (5)	−0.0039 (5)
O4	0.0303 (7)	0.0282 (7)	0.0202 (6)	−0.0094 (5)	0.0104 (5)	−0.0053 (5)
O5	0.0215 (6)	0.0247 (6)	0.0206 (6)	−0.0080 (5)	0.0047 (5)	−0.0030 (5)
O6	0.0209 (6)	0.0287 (7)	0.0230 (7)	−0.0076 (5)	0.0077 (5)	0.0005 (5)
C1	0.0151 (8)	0.0146 (8)	0.0198 (8)	0.0023 (6)	0.0033 (6)	0.0010 (6)
C2	0.0159 (8)	0.0152 (8)	0.0194 (8)	0.0004 (6)	0.0061 (6)	0.0013 (6)
C3	0.0166 (8)	0.0177 (8)	0.0162 (8)	0.0020 (6)	0.0037 (6)	0.0009 (6)
C4	0.0151 (8)	0.0145 (8)	0.0211 (9)	0.0020 (6)	0.0032 (6)	0.0016 (6)
C5	0.0178 (8)	0.0178 (8)	0.0216 (9)	0.0014 (6)	0.0080 (6)	0.0038 (6)
C6	0.0189 (8)	0.0187 (8)	0.0158 (8)	0.0024 (6)	0.0044 (7)	−0.0006 (6)
C7	0.0183 (8)	0.0166 (8)	0.0184 (8)	0.0045 (6)	0.0043 (6)	0.0003 (6)
C8	0.0187 (8)	0.0171 (8)	0.0190 (8)	0.0019 (6)	0.0046 (7)	−0.0004 (6)
C9	0.0190 (8)	0.0164 (8)	0.0205 (9)	0.0043 (6)	0.0063 (7)	0.0011 (6)
C10	0.0165 (8)	0.0131 (7)	0.0202 (8)	0.0033 (6)	0.0046 (6)	0.0002 (6)
C11	0.0206 (8)	0.0167 (8)	0.0167 (8)	0.0022 (6)	0.0054 (7)	0.0000 (6)
C12	0.0159 (7)	0.0141 (8)	0.0214 (9)	0.0016 (6)	0.0039 (6)	−0.0020 (6)
C13	0.0205 (8)	0.0237 (9)	0.0226 (9)	−0.0055 (7)	0.0082 (7)	−0.0034 (7)
C14	0.0164 (8)	0.0153 (8)	0.0228 (9)	0.0031 (6)	0.0073 (6)	0.0018 (6)
C15	0.0205 (8)	0.0212 (9)	0.0178 (8)	0.0021 (6)	0.0054 (7)	0.0013 (6)
C16	0.0168 (8)	0.0158 (8)	0.0206 (9)	0.0025 (6)	0.0025 (6)	−0.0009 (6)
C17	0.0271 (9)	0.0264 (9)	0.0177 (9)	−0.0070 (7)	0.0079 (7)	−0.0006 (6)
C18	0.0196 (9)	0.0225 (9)	0.0266 (9)	−0.0038 (7)	0.0076 (7)	0.0011 (7)
C19	0.0281 (9)	0.0234 (9)	0.0187 (9)	−0.0001 (7)	0.0107 (7)	0.0005 (6)

Geometric parameters (Å, º)

O1—C3	1.3661 (18)	C11—C12	1.366 (2)
O1—C17	1.420 (2)	C12—C14	1.386 (2)
O2—C4	1.3609 (19)	C14—C15	1.376 (2)
O2—C18	1.429 (2)	C15—C16	1.401 (2)
O3—C6	1.3717 (18)	C2—H2	0.9300
O3—C19	1.424 (2)	C5—H5	0.9300
O4—C9	1.2370 (19)	C7—H7	0.9300
O5—C12	1.3769 (19)	C8—H8	0.9300
O5—C13	1.438 (2)	C11—H11	0.9300
O6—C13	1.437 (2)	C13—H13A	0.9700
O6—C14	1.370 (2)	C13—H13B	0.9700
C1—C2	1.414 (2)	C15—H15	0.9300
C1—C6	1.405 (2)	C16—H16	0.9300
C1—C7	1.453 (2)	C17—H17A	0.9600
C2—C3	1.382 (2)	C17—H17B	0.9600
C3—C4	1.413 (2)	C17—H17C	0.9600
C4—C5	1.379 (2)	C18—H18A	0.9600
C5—C6	1.392 (2)	C18—H18B	0.9600
C7—C8	1.343 (2)	C18—H18C	0.9600
C8—C9	1.471 (2)	C19—H19A	0.9600
C9—C10	1.492 (2)	C19—H19B	0.9600
C10—C11	1.415 (2)	C19—H19C	0.9600
C10—C16	1.395 (2)
C3—O1—C17	117.82 (12)	C1—C2—H2	119.00
C4—O2—C18	116.80 (12)	C3—C2—H2	119.00
C6—O3—C19	117.70 (13)	C4—C5—H5	120.00
C12—O5—C13	105.89 (12)	C6—C5—H5	120.00
C13—O6—C14	106.30 (12)	C1—C7—H7	115.00
C2—C1—C6	117.87 (14)	C8—C7—H7	115.00
C2—C1—C7	123.22 (14)	C7—C8—H8	121.00
C6—C1—C7	118.90 (14)	C9—C8—H8	121.00
C1—C2—C3	121.16 (14)	C10—C11—H11	121.00
O1—C3—C2	126.14 (14)	C12—C11—H11	121.00
O1—C3—C4	114.49 (14)	O5—C13—H13A	110.00
C2—C3—C4	119.38 (14)	O5—C13—H13B	110.00
O2—C4—C3	115.07 (14)	O6—C13—H13A	110.00
O2—C4—C5	124.41 (14)	O6—C13—H13B	110.00
C3—C4—C5	120.51 (14)	H13A—C13—H13B	108.00
C4—C5—C6	119.73 (15)	C14—C15—H15	122.00
O3—C6—C1	116.54 (14)	C16—C15—H15	122.00
O3—C6—C5	122.08 (14)	C10—C16—H16	119.00
C1—C6—C5	121.35 (14)	C15—C16—H16	119.00
C1—C7—C8	130.50 (15)	O1—C17—H17A	109.00
C7—C8—C9	118.20 (14)	O1—C17—H17B	110.00
O4—C9—C8	120.37 (15)	O1—C17—H17C	109.00
O4—C9—C10	118.37 (14)	H17A—C17—H17B	110.00
C8—C9—C10	121.25 (14)	H17A—C17—H17C	109.00
C9—C10—C11	116.28 (13)	H17B—C17—H17C	109.00
C9—C10—C16	123.50 (14)	O2—C18—H18A	109.00
C11—C10—C16	120.21 (14)	O2—C18—H18B	109.00
C10—C11—C12	117.09 (14)	O2—C18—H18C	109.00
O5—C12—C11	127.62 (14)	H18A—C18—H18B	109.00
O5—C12—C14	110.01 (13)	H18A—C18—H18C	110.00
C11—C12—C14	122.34 (15)	H18B—C18—H18C	109.00
O5—C13—O6	107.78 (13)	O3—C19—H19A	109.00
O6—C14—C12	109.85 (14)	O3—C19—H19B	109.00
O6—C14—C15	128.27 (15)	O3—C19—H19C	109.00
C12—C14—C15	121.86 (15)	H19A—C19—H19B	109.00
C14—C15—C16	116.77 (15)	H19A—C19—H19C	109.00
C10—C16—C15	121.68 (15)	H19B—C19—H19C	109.00
C17—O1—C3—C2	−0.3 (2)	C2—C3—C4—C5	0.7 (2)
C17—O1—C3—C4	179.87 (13)	O2—C4—C5—C6	179.72 (14)
C18—O2—C4—C3	178.25 (13)	C3—C4—C5—C6	−0.9 (2)
C18—O2—C4—C5	−2.4 (2)	C4—C5—C6—O3	178.47 (15)
C19—O3—C6—C1	−169.19 (14)	C4—C5—C6—C1	0.4 (2)
C19—O3—C6—C5	12.7 (2)	C1—C7—C8—C9	−179.30 (16)
C13—O5—C12—C11	−179.87 (15)	C7—C8—C9—O4	−3.4 (2)
C13—O5—C12—C14	2.25 (17)	C7—C8—C9—C10	177.58 (15)
C12—O5—C13—O6	−3.93 (16)	O4—C9—C10—C11	−9.5 (2)
C14—O6—C13—O5	4.16 (16)	O4—C9—C10—C16	169.88 (15)
C13—O6—C14—C12	−2.82 (17)	C8—C9—C10—C11	169.58 (14)
C13—O6—C14—C15	178.86 (16)	C8—C9—C10—C16	−11.1 (2)
C6—C1—C2—C3	−0.5 (2)	C9—C10—C11—C12	−178.97 (14)
C7—C1—C2—C3	177.87 (15)	C16—C10—C11—C12	1.7 (2)
C2—C1—C6—O3	−177.88 (14)	C9—C10—C16—C15	−179.06 (15)
C2—C1—C6—C5	0.3 (2)	C11—C10—C16—C15	0.2 (2)
C7—C1—C6—O3	3.7 (2)	C10—C11—C12—O5	−179.86 (14)
C7—C1—C6—C5	−178.14 (15)	C10—C11—C12—C14	−2.2 (2)
C2—C1—C7—C8	6.3 (3)	O5—C12—C14—O6	0.37 (18)
C6—C1—C7—C8	−175.42 (17)	O5—C12—C14—C15	178.81 (14)
C1—C2—C3—O1	−179.85 (14)	C11—C12—C14—O6	−177.65 (14)
C1—C2—C3—C4	0.0 (2)	C11—C12—C14—C15	0.8 (2)
O1—C3—C4—O2	0.0 (2)	O6—C14—C15—C16	179.32 (15)
O1—C3—C4—C5	−179.42 (14)	C12—C14—C15—C16	1.2 (2)
C2—C3—C4—O2	−179.86 (14)	C14—C15—C16—C10	−1.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···O4^i	0.97	2.54	3.464 (2)	159

Symmetry code: (i) −x+1/2, y−1/2, −z+3/2.