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In the title mol­ecule, C17H15ClO3, the dihedral angle between the benzene rings is 8.0 (1)°. The crystal structure is stabilized by weak C—H...O and C—H...π inter­actions which link mol­ecules into a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807011233/lh2328sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807011233/lh2328Isup2.hkl
Contains datablock I

CCDC reference: 643056

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.116
  • Data-to-parameter ratio = 20.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.64
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

3-(4-Chlorophenyl)-1-(3,4-dimethoxyphenyl) prop-2-en-1-one top
Crystal data top
C17H15ClO3F(000) = 632
Mr = 302.74Dx = 1.406 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6584 reflections
a = 10.7802 (2) Åθ = 2.5–29.2°
b = 10.3307 (2) ŵ = 0.27 mm1
c = 13.7760 (3) ÅT = 100 K
β = 111.223 (1)°Plate, colourless
V = 1430.14 (5) Å30.49 × 0.34 × 0.16 mm
Z = 4
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
3869 independent reflections
Radiation source: fine-focus sealed tube3169 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
Detector resolution: 8.33 pixels mm-1θmax = 29.2°, θmin = 2.5°
ω scansh = 1314
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1414
Tmin = 0.878, Tmax = 0.957l = 1818
20422 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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0582P)2 + 0.6615P]
where P = (Fo2 + 2Fc2)/3
3869 reflections(Δ/σ)max < 0.001
192 parametersΔρmax = 0.71 e Å3
0 restraintsΔρmin = 0.27 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl11.37873 (4)0.17981 (4)0.37983 (3)0.02234 (12)
O10.26245 (11)0.37143 (11)0.32624 (9)0.0228 (3)
O20.16263 (10)0.18908 (10)0.19305 (9)0.0216 (3)
O30.76107 (11)0.33053 (10)0.44025 (9)0.0213 (3)
C11.02077 (15)0.04479 (15)0.35020 (12)0.0195 (3)
H1A0.93280.07110.31850.023*
C21.12164 (16)0.12307 (15)0.34418 (12)0.0203 (3)
H2A1.10190.20150.30870.024*
C31.25282 (15)0.08339 (14)0.39172 (12)0.0178 (3)
C41.28477 (15)0.03165 (15)0.44669 (13)0.0203 (3)
H4A1.37320.05640.47930.024*
C51.18253 (15)0.10955 (15)0.45233 (13)0.0205 (3)
H5A1.20320.18690.48930.025*
C61.04887 (15)0.07377 (14)0.40339 (12)0.0182 (3)
C70.94441 (16)0.15851 (15)0.41129 (12)0.0190 (3)
H7A0.97230.23530.44790.023*
C80.81355 (15)0.13786 (14)0.37175 (12)0.0183 (3)
H8A0.78080.06320.33330.022*
C90.71967 (15)0.23225 (14)0.38821 (12)0.0174 (3)
C100.57391 (15)0.20857 (14)0.33902 (12)0.0167 (3)
C110.48847 (15)0.29870 (14)0.35929 (12)0.0171 (3)
H11A0.52420.36580.40610.021*
C120.35287 (15)0.28879 (14)0.31080 (12)0.0176 (3)
C130.29760 (15)0.18799 (14)0.23883 (12)0.0170 (3)
C140.38078 (15)0.09670 (14)0.22092 (12)0.0183 (3)
H14A0.34510.02870.17510.022*
C150.51834 (15)0.10682 (14)0.27172 (12)0.0179 (3)
H15A0.57360.04430.26020.021*
C160.31011 (17)0.45900 (16)0.41187 (13)0.0245 (3)
H16A0.23650.50590.41820.037*
H16B0.37150.51870.40020.037*
H16C0.35430.41130.47480.037*
C170.10181 (16)0.08579 (16)0.12260 (13)0.0225 (3)
H17A0.00700.09740.09530.034*
H17B0.12310.00470.15890.034*
H17C0.13450.08600.06640.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0199 (2)0.02051 (19)0.0294 (2)0.00391 (14)0.01231 (16)0.00033 (14)
O10.0177 (5)0.0196 (6)0.0299 (6)0.0048 (4)0.0071 (5)0.0066 (5)
O20.0142 (5)0.0190 (6)0.0290 (6)0.0009 (4)0.0049 (5)0.0041 (4)
O30.0195 (6)0.0155 (5)0.0290 (6)0.0013 (4)0.0089 (5)0.0030 (4)
C10.0146 (7)0.0189 (7)0.0244 (8)0.0015 (6)0.0065 (6)0.0009 (6)
C20.0219 (8)0.0172 (7)0.0228 (8)0.0014 (6)0.0094 (6)0.0016 (6)
C30.0173 (7)0.0163 (7)0.0223 (8)0.0029 (6)0.0100 (6)0.0021 (6)
C40.0161 (7)0.0180 (7)0.0270 (8)0.0020 (6)0.0079 (6)0.0008 (6)
C50.0197 (8)0.0152 (7)0.0274 (8)0.0029 (6)0.0096 (6)0.0024 (6)
C60.0165 (7)0.0149 (7)0.0245 (8)0.0005 (5)0.0090 (6)0.0022 (6)
C70.0199 (8)0.0155 (7)0.0228 (8)0.0001 (6)0.0092 (6)0.0006 (6)
C80.0174 (7)0.0153 (7)0.0228 (8)0.0004 (6)0.0081 (6)0.0001 (6)
C90.0177 (7)0.0147 (7)0.0214 (7)0.0010 (6)0.0091 (6)0.0033 (5)
C100.0170 (7)0.0143 (7)0.0205 (7)0.0008 (5)0.0089 (6)0.0021 (5)
C110.0178 (7)0.0143 (7)0.0197 (7)0.0006 (5)0.0073 (6)0.0008 (5)
C120.0190 (7)0.0137 (7)0.0217 (8)0.0039 (5)0.0093 (6)0.0020 (5)
C130.0146 (7)0.0161 (7)0.0201 (7)0.0007 (5)0.0060 (6)0.0030 (6)
C140.0197 (8)0.0138 (7)0.0220 (8)0.0008 (6)0.0084 (6)0.0006 (5)
C150.0192 (7)0.0130 (7)0.0240 (8)0.0009 (5)0.0111 (6)0.0002 (5)
C160.0245 (8)0.0213 (8)0.0292 (9)0.0012 (6)0.0117 (7)0.0067 (6)
C170.0190 (8)0.0194 (8)0.0269 (8)0.0022 (6)0.0055 (6)0.0014 (6)
Geometric parameters (Å, º) top
Cl1—C31.7385 (15)C8—C91.481 (2)
O1—C121.3691 (18)C8—H8A0.9300
O1—C161.4267 (19)C9—C101.489 (2)
O2—C131.3603 (18)C10—C151.386 (2)
O2—C171.4317 (18)C10—C111.407 (2)
O3—C91.2298 (18)C11—C121.374 (2)
C1—C21.382 (2)C11—H11A0.9300
C1—C61.403 (2)C12—C131.412 (2)
C1—H1A0.9300C13—C141.384 (2)
C2—C31.388 (2)C14—C151.396 (2)
C2—H2A0.9300C14—H14A0.9300
C3—C41.384 (2)C15—H15A0.9300
C4—C51.389 (2)C16—H16A0.9600
C4—H4A0.9300C16—H16B0.9600
C5—C61.401 (2)C16—H16C0.9600
C5—H5A0.9300C17—H17A0.9600
C6—C71.461 (2)C17—H17B0.9600
C7—C81.333 (2)C17—H17C0.9600
C7—H7A0.9300
C12—O1—C16117.41 (12)C15—C10—C9123.94 (13)
C13—O2—C17117.30 (12)C11—C10—C9117.37 (13)
C2—C1—C6121.10 (14)C12—C11—C10120.80 (14)
C2—C1—H1A119.4C12—C11—H11A119.6
C6—C1—H1A119.4C10—C11—H11A119.6
C1—C2—C3119.24 (14)O1—C12—C11124.77 (14)
C1—C2—H2A120.4O1—C12—C13115.19 (13)
C3—C2—H2A120.4C11—C12—C13120.04 (14)
C4—C3—C2121.41 (14)O2—C13—C14125.20 (14)
C4—C3—Cl1119.69 (12)O2—C13—C12115.34 (13)
C2—C3—Cl1118.89 (12)C14—C13—C12119.46 (14)
C3—C4—C5118.85 (14)C13—C14—C15119.93 (14)
C3—C4—H4A120.6C13—C14—H14A120.0
C5—C4—H4A120.6C15—C14—H14A120.0
C4—C5—C6121.24 (14)C10—C15—C14121.04 (14)
C4—C5—H5A119.4C10—C15—H15A119.5
C6—C5—H5A119.4C14—C15—H15A119.5
C5—C6—C1118.14 (14)O1—C16—H16A109.5
C5—C6—C7119.47 (14)O1—C16—H16B109.5
C1—C6—C7122.38 (14)H16A—C16—H16B109.5
C8—C7—C6127.15 (15)O1—C16—H16C109.5
C8—C7—H7A116.4H16A—C16—H16C109.5
C6—C7—H7A116.4H16B—C16—H16C109.5
C7—C8—C9120.87 (14)O2—C17—H17A109.5
C7—C8—H8A119.6O2—C17—H17B109.5
C9—C8—H8A119.6H17A—C17—H17B109.5
O3—C9—C8120.60 (14)O2—C17—H17C109.5
O3—C9—C10120.09 (13)H17A—C17—H17C109.5
C8—C9—C10119.29 (13)H17B—C17—H17C109.5
C15—C10—C11118.63 (14)
C6—C1—C2—C30.0 (2)C8—C9—C10—C11178.13 (13)
C1—C2—C3—C41.3 (2)C15—C10—C11—C122.2 (2)
C1—C2—C3—Cl1177.76 (12)C9—C10—C11—C12175.21 (14)
C2—C3—C4—C51.2 (2)C16—O1—C12—C1112.0 (2)
Cl1—C3—C4—C5177.82 (12)C16—O1—C12—C13168.17 (14)
C3—C4—C5—C60.2 (2)C10—C11—C12—O1179.59 (14)
C4—C5—C6—C11.4 (2)C10—C11—C12—C130.6 (2)
C4—C5—C6—C7179.98 (15)C17—O2—C13—C141.5 (2)
C2—C1—C6—C51.3 (2)C17—O2—C13—C12177.60 (13)
C2—C1—C6—C7179.87 (15)O1—C12—C13—O21.6 (2)
C5—C6—C7—C8178.37 (16)C11—C12—C13—O2178.22 (13)
C1—C6—C7—C80.1 (3)O1—C12—C13—C14177.61 (13)
C6—C7—C8—C9178.76 (14)C11—C12—C13—C142.6 (2)
C7—C8—C9—O31.2 (2)O2—C13—C14—C15179.15 (14)
C7—C8—C9—C10177.40 (14)C12—C13—C14—C151.7 (2)
O3—C9—C10—C15173.98 (14)C11—C10—C15—C143.0 (2)
C8—C9—C10—C154.7 (2)C9—C10—C15—C14174.16 (14)
O3—C9—C10—C113.2 (2)C13—C14—C15—C101.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···Cg2i0.933.263.574 (2)102
C17—H17B···Cg1ii0.963.203.756 (2)119
C1—H1A···O1iii0.932.393.257 (2)155
C7—H7A···O30.932.452.792 (2)102
C14—H14A···O3iii0.932.593.517 (2)175
C16—H16A···O3iv0.962.573.256 (2)128
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x+1, y1/2, z+1/2; (iv) x+1, y+1, z+1.
 

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