(2E)-1-(2,4-Dichloro­phen­yl)-3-(6-meth­oxy-2-naphth­yl)prop-2-en-1-one

The geometric parameters of the title mol­ecule, C₂₀H₁₄Cl₂O₂, are in the normal ranges. The central C=C double bond is trans configured and the two C atoms of this bond are slightly twisted out of the plane of the naphthyl group by 4.0 (3)°. The dihedral angle between the benzene ring and the naphthalene ring system is 44.94 (4)°. The crystal packing is stabilized by C—H...O and C—H...Cl contacts.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.034
• wR factor = 0.090
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.71

   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

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.

(2E)-1-(2,4-Dichlorophenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one

Crystal data

C20H14Cl2O2	F(000) = 736
Mr = 357.21	Dx = 1.430 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 28156 reflections
a = 16.8724 (7) Å	θ = 2.1–25.9°
b = 13.4610 (7) Å	µ = 0.40 mm^−1
c = 7.4932 (3) Å	T = 173 K
β = 102.778 (3)°	Block, yellow
V = 1659.70 (13) Å^3	0.37 × 0.35 × 0.35 mm
Z = 4

Data collection

Stoe IPDS-II two-circle diffractometer	3143 independent reflections
Radiation source: fine-focus sealed tube	2984 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
ω scans	θmax = 25.7°, θmin = 2.0°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −20→20
Tmin = 0.866, Tmax = 0.873	k = −16→16
28868 measured reflections	l = −9→9

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.090	w = 1/[σ^2(Fo^2) + (0.041P)^2 + 0.8551P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
3143 reflections	Δρmax = 0.57 e Å^−3
219 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0156 (15)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.08388 (2)	0.47002 (3)	0.33683 (6)	0.03875 (15)
Cl2	−0.21050 (3)	0.38127 (4)	−0.07346 (7)	0.04839 (16)
O1	0.13175 (7)	0.15878 (8)	0.35253 (15)	0.0318 (3)
O2	0.72294 (7)	0.44234 (10)	0.39635 (18)	0.0423 (3)
C1	0.12626 (9)	0.24246 (11)	0.2858 (2)	0.0257 (3)
C2	0.19809 (9)	0.30125 (12)	0.2714 (2)	0.0266 (3)
H2	0.1911	0.3603	0.2001	0.032*
C3	0.27317 (9)	0.27332 (12)	0.3566 (2)	0.0268 (3)
H3	0.2773	0.2156	0.4310	0.032*
C11	0.04296 (9)	0.28323 (11)	0.20507 (19)	0.0240 (3)
C12	0.01860 (9)	0.38228 (11)	0.2114 (2)	0.0266 (3)
C13	−0.05912 (9)	0.41356 (12)	0.1282 (2)	0.0313 (4)
H13	−0.0746	0.4812	0.1331	0.038*
C14	−0.11359 (9)	0.34350 (13)	0.0376 (2)	0.0310 (4)
C15	−0.09343 (9)	0.24384 (13)	0.0324 (2)	0.0305 (3)
H15	−0.1322	0.1966	−0.0273	0.037*
C16	−0.01524 (9)	0.21503 (12)	0.1167 (2)	0.0274 (3)
H16	−0.0007	0.1469	0.1145	0.033*
C21	0.34928 (9)	0.32241 (12)	0.3468 (2)	0.0265 (3)
C22	0.35197 (9)	0.41289 (12)	0.2500 (2)	0.0297 (3)
H22	0.3025	0.4441	0.1913	0.036*
C23	0.42448 (10)	0.45594 (12)	0.2397 (2)	0.0304 (3)
H23	0.4243	0.5165	0.1745	0.036*
C24	0.49968 (9)	0.41176 (12)	0.3248 (2)	0.0272 (3)
C25	0.49795 (9)	0.32241 (12)	0.4238 (2)	0.0277 (3)
C26	0.42243 (9)	0.27962 (12)	0.4333 (2)	0.0284 (3)
H26	0.4218	0.2200	0.5008	0.034*
C27	0.57561 (10)	0.45447 (12)	0.3126 (2)	0.0306 (3)
H27	0.5771	0.5141	0.2455	0.037*
C28	0.64653 (10)	0.40898 (13)	0.3984 (2)	0.0318 (4)
C29	0.64557 (10)	0.32000 (13)	0.4992 (2)	0.0344 (4)
H29	0.6952	0.2894	0.5581	0.041*
C30	0.57314 (10)	0.27834 (13)	0.5115 (2)	0.0327 (4)
H30	0.5730	0.2189	0.5798	0.039*
C31	0.72840 (12)	0.53044 (15)	0.2942 (3)	0.0440 (5)
H31A	0.7005	0.5201	0.1662	0.066*
H31B	0.7857	0.5461	0.3004	0.066*
H31C	0.7028	0.5856	0.3456	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0305 (2)	0.0271 (2)	0.0548 (3)	−0.00103 (15)	0.00107 (18)	−0.00898 (17)
Cl2	0.0259 (2)	0.0451 (3)	0.0665 (3)	0.00445 (17)	−0.0063 (2)	0.0058 (2)
O1	0.0319 (6)	0.0280 (6)	0.0348 (6)	0.0041 (5)	0.0054 (5)	0.0040 (5)
O2	0.0295 (6)	0.0498 (8)	0.0461 (7)	−0.0111 (5)	0.0051 (5)	0.0051 (6)
C1	0.0275 (8)	0.0284 (8)	0.0211 (7)	0.0033 (6)	0.0056 (6)	−0.0024 (6)
C2	0.0254 (7)	0.0291 (8)	0.0253 (7)	0.0023 (6)	0.0057 (6)	0.0010 (6)
C3	0.0280 (8)	0.0290 (8)	0.0233 (7)	0.0030 (6)	0.0056 (6)	−0.0015 (6)
C11	0.0235 (7)	0.0265 (7)	0.0230 (7)	0.0008 (6)	0.0072 (6)	0.0017 (6)
C12	0.0249 (7)	0.0254 (8)	0.0296 (8)	−0.0015 (6)	0.0062 (6)	0.0004 (6)
C13	0.0287 (8)	0.0262 (8)	0.0391 (9)	0.0033 (6)	0.0078 (7)	0.0039 (7)
C14	0.0230 (7)	0.0353 (9)	0.0339 (8)	0.0022 (6)	0.0041 (6)	0.0047 (7)
C15	0.0263 (8)	0.0330 (8)	0.0314 (8)	−0.0043 (6)	0.0050 (6)	−0.0009 (7)
C16	0.0293 (8)	0.0254 (8)	0.0288 (8)	0.0004 (6)	0.0089 (6)	−0.0002 (6)
C21	0.0247 (7)	0.0307 (8)	0.0234 (7)	0.0023 (6)	0.0041 (6)	−0.0025 (6)
C22	0.0277 (8)	0.0300 (8)	0.0296 (8)	0.0053 (6)	0.0022 (6)	−0.0004 (6)
C23	0.0337 (8)	0.0260 (8)	0.0304 (8)	0.0011 (6)	0.0048 (6)	0.0007 (6)
C24	0.0297 (8)	0.0279 (8)	0.0234 (7)	−0.0017 (6)	0.0045 (6)	−0.0049 (6)
C25	0.0257 (7)	0.0324 (8)	0.0240 (7)	0.0012 (6)	0.0036 (6)	−0.0021 (6)
C26	0.0278 (8)	0.0310 (8)	0.0257 (7)	0.0019 (6)	0.0045 (6)	0.0038 (6)
C27	0.0339 (8)	0.0301 (8)	0.0271 (8)	−0.0051 (6)	0.0049 (6)	−0.0036 (6)
C28	0.0287 (8)	0.0364 (9)	0.0299 (8)	−0.0079 (7)	0.0056 (6)	−0.0046 (7)
C29	0.0278 (8)	0.0408 (10)	0.0328 (8)	−0.0018 (7)	0.0026 (6)	0.0026 (7)
C30	0.0293 (8)	0.0347 (9)	0.0325 (8)	0.0019 (7)	0.0034 (6)	0.0078 (7)
C31	0.0429 (10)	0.0499 (11)	0.0403 (10)	−0.0177 (9)	0.0114 (8)	−0.0001 (8)

Geometric parameters (Å, º)

Cl1—C12	1.7416 (16)	C21—C26	1.386 (2)
Cl2—C14	1.7385 (16)	C21—C22	1.424 (2)
O1—C1	1.2275 (19)	C22—C23	1.371 (2)
O2—C28	1.3684 (19)	C22—H22	0.9500
O2—C31	1.426 (2)	C23—C24	1.418 (2)
C1—C2	1.471 (2)	C23—H23	0.9500
C1—C11	1.505 (2)	C24—C25	1.417 (2)
C2—C3	1.340 (2)	C24—C27	1.425 (2)
C2—H2	0.9500	C25—C26	1.414 (2)
C3—C21	1.460 (2)	C25—C30	1.423 (2)
C3—H3	0.9500	C26—H26	0.9500
C11—C16	1.399 (2)	C27—C28	1.371 (2)
C11—C12	1.399 (2)	C27—H27	0.9500
C12—C13	1.387 (2)	C28—C29	1.418 (2)
C13—C14	1.385 (2)	C29—C30	1.366 (2)
C13—H13	0.9500	C29—H29	0.9500
C14—C15	1.387 (2)	C30—H30	0.9500
C15—C16	1.386 (2)	C31—H31A	0.9800
C15—H15	0.9500	C31—H31B	0.9800
C16—H16	0.9500	C31—H31C	0.9800
C28—O2—C31	116.86 (14)	C23—C22—H22	119.3
O1—C1—C2	122.29 (14)	C21—C22—H22	119.3
O1—C1—C11	118.55 (14)	C22—C23—C24	121.21 (15)
C2—C1—C11	119.03 (13)	C22—C23—H23	119.4
C3—C2—C1	121.42 (14)	C24—C23—H23	119.4
C3—C2—H2	119.3	C25—C24—C23	118.11 (14)
C1—C2—H2	119.3	C25—C24—C27	119.92 (14)
C2—C3—C21	126.75 (15)	C23—C24—C27	121.97 (15)
C2—C3—H3	116.6	C26—C25—C24	119.68 (14)
C21—C3—H3	116.6	C26—C25—C30	121.88 (15)
C16—C11—C12	117.43 (14)	C24—C25—C30	118.44 (14)
C16—C11—C1	116.49 (13)	C21—C26—C25	121.74 (15)
C12—C11—C1	126.08 (13)	C21—C26—H26	119.1
C13—C12—C11	121.97 (14)	C25—C26—H26	119.1
C13—C12—Cl1	117.32 (12)	C28—C27—C24	119.57 (15)
C11—C12—Cl1	120.60 (12)	C28—C27—H27	120.2
C14—C13—C12	118.20 (15)	C24—C27—H27	120.2
C14—C13—H13	120.9	O2—C28—C27	125.10 (16)
C12—C13—H13	120.9	O2—C28—C29	113.88 (15)
C13—C14—C15	122.15 (15)	C27—C28—C29	121.02 (15)
C13—C14—Cl2	119.16 (13)	C30—C29—C28	119.89 (15)
C15—C14—Cl2	118.69 (13)	C30—C29—H29	120.1
C16—C15—C14	118.20 (15)	C28—C29—H29	120.1
C16—C15—H15	120.9	C29—C30—C25	121.15 (16)
C14—C15—H15	120.9	C29—C30—H30	119.4
C15—C16—C11	121.99 (15)	C25—C30—H30	119.4
C15—C16—H16	119.0	O2—C31—H31A	109.5
C11—C16—H16	119.0	O2—C31—H31B	109.5
C26—C21—C22	117.93 (14)	H31A—C31—H31B	109.5
C26—C21—C3	119.38 (14)	O2—C31—H31C	109.5
C22—C21—C3	122.69 (14)	H31A—C31—H31C	109.5
C23—C22—C21	121.30 (14)	H31B—C31—H31C	109.5
O1—C1—C2—C3	−10.9 (2)	C3—C21—C22—C23	−178.42 (15)
C11—C1—C2—C3	173.17 (14)	C21—C22—C23—C24	0.2 (2)
C1—C2—C3—C21	177.14 (14)	C22—C23—C24—C25	−1.1 (2)
O1—C1—C11—C16	−35.40 (19)	C22—C23—C24—C27	178.78 (15)
C2—C1—C11—C16	140.64 (14)	C23—C24—C25—C26	0.7 (2)
O1—C1—C11—C12	144.14 (15)	C27—C24—C25—C26	−179.13 (14)
C2—C1—C11—C12	−39.8 (2)	C23—C24—C25—C30	−179.18 (14)
C16—C11—C12—C13	−2.4 (2)	C27—C24—C25—C30	1.0 (2)
C1—C11—C12—C13	178.07 (14)	C22—C21—C26—C25	−1.3 (2)
C16—C11—C12—Cl1	173.88 (11)	C3—C21—C26—C25	178.09 (14)
C1—C11—C12—Cl1	−5.7 (2)	C24—C25—C26—C21	0.5 (2)
C11—C12—C13—C14	0.4 (2)	C30—C25—C26—C21	−179.61 (15)
Cl1—C12—C13—C14	−175.96 (12)	C25—C24—C27—C28	−0.5 (2)
C12—C13—C14—C15	1.8 (2)	C23—C24—C27—C28	179.60 (15)
C12—C13—C14—Cl2	−178.20 (12)	C31—O2—C28—C27	−1.1 (2)
C13—C14—C15—C16	−1.9 (2)	C31—O2—C28—C29	178.73 (15)
Cl2—C14—C15—C16	178.10 (12)	C24—C27—C28—O2	179.78 (15)
C14—C15—C16—C11	−0.2 (2)	C24—C27—C28—C29	0.0 (2)
C12—C11—C16—C15	2.3 (2)	O2—C28—C29—C30	−179.68 (16)
C1—C11—C16—C15	−178.14 (14)	C27—C28—C29—C30	0.1 (3)
C2—C3—C21—C26	−175.37 (15)	C28—C29—C30—C25	0.3 (3)
C2—C3—C21—C22	4.0 (2)	C26—C25—C30—C29	179.24 (16)
C26—C21—C22—C23	1.0 (2)	C24—C25—C30—C29	−0.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1^i	0.95	2.59	3.1367 (19)	117
C13—H13···O1^ii	0.95	2.59	3.535 (2)	174
C16—H16···Cl1^iii	0.95	2.83	3.5381 (16)	132

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2.