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In the title compound, C16H10Cl2O3, the olefinic double bond adopts an E conformation [C—C=C—C torsion angle = −172.9 (3)°]. The dihedral angle between the benzodioxole and di­chloro­benzene rings is 5.57 (9)°. In the crystal, mol­ecules are linked by weak C—H...O and C—H...Cl hydrogen bonds, forming chains propagating along the c-axis direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314617001031/sj4082sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314617001031/sj4082Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314617001031/sj4082Isup3.cml
Supplementary material

CCDC reference: 1528716

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.052
  • wR factor = 0.158
  • Data-to-parameter ratio = 11.7

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 = 0.5855 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low . 0.976 Note PLAT397_ALERT_2_C Deviating C-O-C Angle from 120 Deg for O1 106.4 Degree PLAT397_ALERT_2_C Deviating C-O-C Angle from 120 Deg for O2 105.6 Degree PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.586 56 Report
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 PLAT431_ALERT_2_G Short Inter HL..A Contact Cl1 .. O2 .. 3.02 Ang. PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still 78 % Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 2 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 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 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.
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 top

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-(Benzo[d][1,3]dioxol-5-yl)-3-(2,3-dichlorophenyl)prop-2-en-1-one top
Crystal data top
C16H10Cl2O3F(000) = 656
Mr = 321.14Dx = 1.568 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybcCell parameters from 2086 reflections
a = 10.1854 (7) Åθ = 4.4–64.5°
b = 11.0820 (8) ŵ = 4.36 mm1
c = 12.2077 (9) ÅT = 296 K
β = 99.068 (3)°Rectangle, white
V = 1360.72 (17) Å30.28 × 0.26 × 0.24 mm
Z = 4
Data collection top
Bruker X8 Proteum
diffractometer
2232 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode2086 reflections with I > 2σ(I)
Helios multilayer optics monochromatorRint = 0.048
Detector resolution: 18.4 pixels mm-1θmax = 64.5°, θmin = 4.4°
φ and ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
k = 1012
Tmin = 0.375, Tmax = 0.421l = 1413
8712 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.1218P)2 + 0.554P]
where P = (Fo2 + 2Fc2)/3
2232 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = 0.38 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl10.13750 (6)0.03536 (6)0.24874 (5)0.0316 (3)
Cl20.37087 (6)0.00563 (6)0.38206 (6)0.0377 (3)
O10.76711 (18)0.39765 (18)0.31535 (15)0.0353 (6)
O20.80348 (18)0.45912 (17)0.49834 (15)0.0322 (6)
O30.3035 (2)0.20086 (19)0.24062 (16)0.0393 (7)
C10.8544 (3)0.4624 (2)0.3945 (2)0.0304 (8)
C20.6590 (2)0.3683 (2)0.3649 (2)0.0260 (7)
C30.5445 (2)0.3131 (2)0.3184 (2)0.0272 (8)
C40.4480 (2)0.2919 (2)0.3881 (2)0.0261 (7)
C50.4743 (3)0.3250 (2)0.4999 (2)0.0273 (7)
C60.5927 (2)0.3814 (2)0.5459 (2)0.0282 (7)
C70.3208 (3)0.2367 (2)0.3373 (2)0.0292 (8)
C80.2132 (3)0.2262 (3)0.4053 (2)0.0353 (8)
C90.1024 (3)0.1677 (2)0.3710 (2)0.0287 (8)
C100.0084 (2)0.1487 (2)0.4320 (2)0.0252 (7)
C110.1248 (2)0.0878 (2)0.3834 (2)0.0255 (7)
C120.2286 (2)0.0698 (2)0.4426 (2)0.0273 (8)
C130.2211 (3)0.1102 (2)0.5504 (2)0.0311 (8)
C140.1074 (3)0.1695 (2)0.5994 (2)0.0311 (8)
C150.0023 (3)0.1880 (2)0.5422 (2)0.0284 (8)
C160.6823 (2)0.4034 (2)0.4754 (2)0.0256 (7)
H10.861100.545200.370400.0360*
H30.942300.426400.403600.0360*
H50.410900.308800.545000.0330*
H60.610000.403000.620400.0340*
H80.224500.262500.474900.0420*
H90.093400.134700.300200.0340*
H100.530100.290200.244200.0330*
H130.291300.097700.589400.0370*
H140.101600.197300.671800.0370*
H150.073600.227200.577200.0340*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0261 (4)0.0429 (5)0.0243 (4)0.0032 (2)0.0007 (3)0.0032 (2)
Cl20.0241 (4)0.0427 (5)0.0458 (5)0.0060 (3)0.0038 (3)0.0033 (3)
O10.0295 (10)0.0491 (11)0.0295 (10)0.0069 (8)0.0113 (8)0.0014 (8)
O20.0233 (10)0.0450 (11)0.0277 (10)0.0076 (8)0.0026 (8)0.0003 (8)
O30.0365 (11)0.0494 (12)0.0314 (11)0.0144 (9)0.0039 (8)0.0068 (9)
C10.0240 (13)0.0345 (14)0.0344 (15)0.0024 (11)0.0103 (11)0.0075 (11)
C20.0224 (12)0.0284 (13)0.0274 (12)0.0036 (10)0.0045 (10)0.0040 (10)
C30.0279 (13)0.0290 (13)0.0246 (13)0.0002 (10)0.0042 (10)0.0016 (10)
C40.0240 (13)0.0234 (12)0.0303 (13)0.0023 (10)0.0027 (10)0.0005 (10)
C50.0231 (12)0.0290 (13)0.0307 (13)0.0012 (10)0.0069 (10)0.0051 (10)
C60.0273 (13)0.0342 (13)0.0229 (12)0.0005 (11)0.0037 (10)0.0023 (10)
C70.0282 (14)0.0260 (12)0.0334 (14)0.0007 (10)0.0048 (11)0.0015 (10)
C80.0293 (14)0.0390 (15)0.0387 (15)0.0037 (12)0.0092 (12)0.0097 (12)
C90.0308 (14)0.0293 (13)0.0245 (12)0.0035 (11)0.0004 (11)0.0002 (10)
C100.0258 (13)0.0201 (12)0.0286 (13)0.0010 (10)0.0013 (10)0.0026 (10)
C110.0268 (13)0.0233 (12)0.0245 (12)0.0034 (10)0.0015 (10)0.0008 (10)
C120.0218 (13)0.0216 (12)0.0369 (14)0.0021 (10)0.0005 (11)0.0008 (10)
C130.0310 (14)0.0275 (13)0.0365 (14)0.0056 (11)0.0103 (11)0.0025 (11)
C140.0392 (15)0.0249 (13)0.0302 (13)0.0001 (11)0.0086 (11)0.0031 (10)
C150.0320 (14)0.0237 (13)0.0280 (13)0.0030 (10)0.0001 (10)0.0003 (10)
C160.0217 (12)0.0251 (12)0.0286 (13)0.0015 (10)0.0002 (10)0.0043 (10)
Geometric parameters (Å, º) top
Cl1—C111.729 (2)C10—C111.411 (3)
Cl2—C121.734 (2)C10—C151.406 (3)
O1—C11.403 (3)C11—C121.386 (3)
O1—C21.376 (3)C12—C131.381 (3)
O2—C11.444 (3)C13—C141.383 (4)
O2—C161.369 (3)C14—C151.383 (4)
O3—C71.231 (3)C1—H10.9700
C2—C31.359 (3)C1—H30.9700
C2—C161.388 (3)C3—H100.9300
C3—C41.417 (3)C5—H50.9300
C4—C51.398 (3)C6—H60.9300
C4—C71.478 (4)C8—H80.9300
C5—C61.395 (4)C9—H90.9300
C6—C161.371 (3)C13—H130.9300
C7—C81.480 (4)C14—H140.9300
C8—C91.312 (4)C15—H150.9300
C9—C101.462 (4)
C1—O1—C2106.40 (19)C13—C14—C15121.0 (2)
C1—O2—C16105.59 (19)C10—C15—C14121.1 (2)
O1—C1—O2108.4 (2)O2—C16—C2109.62 (19)
O1—C2—C3128.0 (2)O2—C16—C6128.3 (2)
O1—C2—C16109.56 (19)C2—C16—C6122.1 (2)
C3—C2—C16122.4 (2)O1—C1—H1110.00
C2—C3—C4117.0 (2)O1—C1—H3110.00
C3—C4—C5119.9 (2)O2—C1—H1110.00
C3—C4—C7117.5 (2)O2—C1—H3110.00
C5—C4—C7122.6 (2)H1—C1—H3108.00
C4—C5—C6122.1 (2)C2—C3—H10122.00
C5—C6—C16116.5 (2)C4—C3—H10121.00
O3—C7—C4121.3 (3)C4—C5—H5119.00
O3—C7—C8120.4 (3)C6—C5—H5119.00
C4—C7—C8118.4 (2)C5—C6—H6122.00
C7—C8—C9122.4 (2)C16—C6—H6122.00
C8—C9—C10127.1 (2)C7—C8—H8119.00
C9—C10—C11121.3 (2)C9—C8—H8119.00
C9—C10—C15121.4 (2)C8—C9—H9116.00
C11—C10—C15117.3 (2)C10—C9—H9116.00
Cl1—C11—C10119.50 (17)C12—C13—H13121.00
Cl1—C11—C12119.90 (17)C14—C13—H13121.00
C10—C11—C12120.6 (2)C13—C14—H14120.00
Cl2—C12—C11120.14 (18)C15—C14—H14120.00
Cl2—C12—C13118.65 (19)C10—C15—H15120.00
C11—C12—C13121.2 (2)C14—C15—H15119.00
C12—C13—C14118.9 (2)
C2—O1—C1—O26.8 (2)C5—C6—C16—O2178.6 (2)
C1—O1—C2—C3174.9 (2)C5—C6—C16—C22.0 (3)
C1—O1—C2—C165.4 (3)O3—C7—C8—C97.6 (4)
C16—O2—C1—O15.7 (2)C4—C7—C8—C9172.9 (3)
C1—O2—C16—C22.4 (2)C7—C8—C9—C10178.1 (2)
C1—O2—C16—C6178.1 (2)C8—C9—C10—C11177.4 (3)
O1—C2—C3—C4179.5 (2)C8—C9—C10—C154.0 (4)
C16—C2—C3—C40.2 (3)C9—C10—C11—Cl10.4 (3)
O1—C2—C16—O21.8 (3)C9—C10—C11—C12179.6 (2)
O1—C2—C16—C6177.7 (2)C15—C10—C11—Cl1179.11 (17)
C3—C2—C16—O2178.5 (2)C15—C10—C11—C120.9 (3)
C3—C2—C16—C62.0 (4)C9—C10—C15—C14179.9 (2)
C2—C3—C4—C51.5 (3)C11—C10—C15—C141.2 (3)
C2—C3—C4—C7177.4 (2)Cl1—C11—C12—Cl20.2 (3)
C3—C4—C5—C61.4 (3)Cl1—C11—C12—C13179.73 (18)
C7—C4—C5—C6177.4 (2)C10—C11—C12—Cl2179.78 (17)
C3—C4—C7—O36.2 (3)C10—C11—C12—C130.3 (3)
C3—C4—C7—C8173.3 (2)Cl2—C12—C13—C14179.45 (18)
C5—C4—C7—O3175.0 (2)C11—C12—C13—C140.1 (3)
C5—C4—C7—C85.5 (3)C12—C13—C14—C150.3 (4)
C4—C5—C6—C160.3 (3)C13—C14—C15—C100.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···Cl10.932.583.033 (3)110
C9—H9···O30.932.482.809 (4)101
C14—H14···O1i0.932.593.194 (3)123
Symmetry code: (i) x1, y+1/2, z+1/2.
 

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