3-(2,4-Dichloro­phen­yl)-1-(4-methoxyphen­yl)prop-2-en-1-one

Rosli, M.M.; Patil, P.S.; Fun, H.-K.; Razak, I.A.; Puranik, V.G.; Dharmaprakash, S.M.

doi:10.1107/S1600536806039006

3-(2,4-Dichlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one

M. M. Rosli, P. S. Patil, H.-K. Fun, I. A. Razak, V. G. Puranik and S. M. Dharmaprakash

In the title compound, C₁₆H₁₂Cl₂O₂, the dihedral angle between the benzene rings is 28.63 (6)°. The crystal structure is stabilized by intermolecular C—H

O hydrogen bonds and by short Cl

Cl interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806039006/sj2130sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806039006/sj2130Isup2.hkl Contains datablock I

CCDC reference: 628399

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Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C)= 0.002 Å
R factor = 0.049
wR factor = 0.116
Data-to-parameter ratio = 34.8

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No errors found in this datablock

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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: H.K. Fun and I.A. Razak are supervisors of M.M. Rosli whereas S.M. Dharmaprakash is the supervisor of P.S. Patil and Vedavati G. Puranik in this collaborative publication. Mangalore University and National Chemical Laboratory, India is involved in the extraction and synthesis of the title compound and USM is involved in the structure determination. All parties are involved in writing up the manuscript.


   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, 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-(2,4-Dichlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₂Cl₂O₂	F(000) = 1264
M_r = 307.16	D_x = 1.475 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5935 reflections
a = 7.1676 (1) Å	θ = 2.4–35.6°
b = 11.1505 (2) Å	µ = 0.47 mm⁻¹
c = 34.6112 (5) Å	T = 100 K
V = 2766.21 (7) Å³	Block, yellow
Z = 8	0.49 × 0.25 × 0.23 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6337 independent reflections
Radiation source: fine-focus sealed tube	4966 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
Detector resolution: 8.33 pixels mm^-1	θ_max = 35.6°, θ_min = 1.2°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −18→17
T_min = 0.808, T_max = 0.900	l = −56→52
62000 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0435P)² + 1.3505P] where P = (F_o² + 2F_c²)/3
6337 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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

	x	y	z	U_iso*/U_eq
Cl1	0.44706 (6)	0.40078 (3)	0.063968 (9)	0.03001 (9)
Cl2	0.47854 (6)	0.84709 (3)	0.007057 (10)	0.03600 (10)
O1	0.68608 (14)	0.33372 (8)	0.19368 (3)	0.02448 (19)
O2	0.61171 (15)	0.51343 (9)	0.36564 (3)	0.0259 (2)
C1	0.59437 (17)	0.57632 (10)	0.26127 (3)	0.0187 (2)
H1A	0.5701	0.6387	0.2442	0.022*
C2	0.58249 (17)	0.59731 (10)	0.30090 (3)	0.0195 (2)
H2A	0.5507	0.6729	0.3101	0.023*
C3	0.61860 (17)	0.50425 (11)	0.32646 (3)	0.0197 (2)
C4	0.66545 (18)	0.39008 (11)	0.31234 (4)	0.0224 (2)
H4A	0.6891	0.3276	0.3294	0.027*
C5	0.67627 (18)	0.37105 (10)	0.27313 (4)	0.0205 (2)
H5A	0.7070	0.2952	0.2640	0.025*
C6	0.64194 (16)	0.46363 (10)	0.24672 (3)	0.01767 (19)
C7	0.65504 (17)	0.43686 (10)	0.20479 (3)	0.0188 (2)
C8	0.62814 (18)	0.53529 (11)	0.17638 (3)	0.0206 (2)
H8A	0.6380	0.6150	0.1841	0.025*
C9	0.58965 (18)	0.50787 (11)	0.13961 (3)	0.0206 (2)
H9A	0.5816	0.4267	0.1336	0.025*
C10	0.55885 (17)	0.59181 (11)	0.10780 (3)	0.0197 (2)
C11	0.49588 (19)	0.55209 (11)	0.07163 (4)	0.0216 (2)
C12	0.4680 (2)	0.62882 (12)	0.04057 (4)	0.0248 (2)
H12A	0.4253	0.6000	0.0170	0.030*
C13	0.5058 (2)	0.74996 (12)	0.04577 (4)	0.0251 (2)
C14	0.5654 (2)	0.79463 (12)	0.08119 (4)	0.0249 (2)
H14A	0.5879	0.8762	0.0844	0.030*
C15	0.59092 (18)	0.71601 (11)	0.11165 (4)	0.0223 (2)
H15A	0.6304	0.7459	0.1354	0.027*
C16	0.5748 (2)	0.62859 (12)	0.38195 (4)	0.0261 (3)
H16A	0.5674	0.6218	0.4096	0.039*
H16B	0.4586	0.6586	0.3721	0.039*
H16C	0.6736	0.6828	0.3752	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0471 (2)	0.02095 (14)	0.02200 (14)	−0.00628 (13)	−0.00572 (13)	−0.00217 (10)
Cl2	0.0525 (2)	0.02803 (17)	0.02751 (17)	0.00807 (15)	0.00662 (15)	0.00880 (12)
O1	0.0299 (5)	0.0165 (4)	0.0270 (4)	0.0008 (3)	0.0007 (4)	−0.0030 (3)
O2	0.0348 (5)	0.0225 (4)	0.0204 (4)	0.0004 (4)	0.0014 (4)	0.0019 (3)
C1	0.0206 (5)	0.0146 (4)	0.0210 (5)	−0.0004 (4)	−0.0018 (4)	0.0013 (4)
C2	0.0220 (5)	0.0150 (5)	0.0216 (5)	0.0002 (4)	−0.0004 (4)	0.0000 (4)
C3	0.0202 (5)	0.0191 (5)	0.0197 (5)	−0.0010 (4)	0.0001 (4)	0.0018 (4)
C4	0.0251 (6)	0.0174 (5)	0.0246 (5)	0.0023 (4)	0.0009 (4)	0.0043 (4)
C5	0.0216 (5)	0.0142 (4)	0.0258 (5)	0.0011 (4)	0.0008 (4)	0.0017 (4)
C6	0.0167 (5)	0.0145 (4)	0.0218 (5)	−0.0007 (4)	−0.0003 (4)	0.0006 (4)
C7	0.0175 (5)	0.0166 (5)	0.0223 (5)	−0.0016 (4)	−0.0004 (4)	−0.0007 (4)
C8	0.0234 (5)	0.0169 (5)	0.0215 (5)	−0.0015 (4)	−0.0003 (4)	−0.0004 (4)
C9	0.0220 (5)	0.0182 (5)	0.0216 (5)	−0.0006 (4)	−0.0009 (4)	−0.0014 (4)
C10	0.0202 (5)	0.0186 (5)	0.0202 (5)	−0.0002 (4)	0.0010 (4)	−0.0009 (4)
C11	0.0257 (6)	0.0187 (5)	0.0203 (5)	−0.0006 (4)	0.0011 (4)	−0.0018 (4)
C12	0.0316 (7)	0.0238 (5)	0.0191 (5)	0.0025 (5)	0.0012 (5)	0.0008 (4)
C13	0.0301 (6)	0.0225 (5)	0.0228 (5)	0.0048 (5)	0.0050 (5)	0.0038 (4)
C14	0.0283 (6)	0.0186 (5)	0.0278 (6)	0.0016 (5)	0.0033 (5)	0.0003 (4)
C15	0.0232 (6)	0.0200 (5)	0.0239 (5)	0.0007 (4)	0.0008 (4)	−0.0026 (4)
C16	0.0289 (7)	0.0260 (6)	0.0234 (6)	0.0002 (5)	0.0024 (5)	−0.0016 (4)

Geometric parameters (Å, º) top

Cl1—C11	1.7435 (13)	C8—C9	1.3373 (17)
Cl2—C13	1.7340 (13)	C8—H8A	0.9300
O1—C7	1.2329 (14)	C9—C10	1.4618 (17)
O2—C3	1.3610 (15)	C9—H9A	0.9300
O2—C16	1.4274 (16)	C10—C11	1.4026 (17)
C1—C2	1.3940 (17)	C10—C15	1.4101 (17)
C1—C6	1.3960 (16)	C11—C12	1.3883 (18)
C1—H1A	0.9300	C12—C13	1.3892 (19)
C2—C3	1.3880 (16)	C12—H12A	0.9300
C2—H2A	0.9300	C13—C14	1.3907 (19)
C3—C4	1.4042 (17)	C14—C15	1.3832 (18)
C4—C5	1.3759 (18)	C14—H14A	0.9300
C4—H4A	0.9300	C15—H15A	0.9300
C5—C6	1.4006 (16)	C16—H16A	0.9600
C5—H5A	0.9300	C16—H16B	0.9600
C6—C7	1.4848 (17)	C16—H16C	0.9600
C7—C8	1.4862 (17)

C3—O2—C16	117.93 (10)	C8—C9—H9A	116.5
C2—C1—C6	121.39 (11)	C10—C9—H9A	116.5
C2—C1—H1A	119.3	C11—C10—C15	116.54 (11)
C6—C1—H1A	119.3	C11—C10—C9	121.24 (11)
C3—C2—C1	119.36 (11)	C15—C10—C9	122.21 (11)
C3—C2—H2A	120.3	C12—C11—C10	122.88 (12)
C1—C2—H2A	120.3	C12—C11—Cl1	116.73 (10)
O2—C3—C2	124.90 (11)	C10—C11—Cl1	120.40 (9)
O2—C3—C4	115.06 (11)	C11—C12—C13	118.09 (12)
C2—C3—C4	120.04 (11)	C11—C12—H12A	121.0
C5—C4—C3	119.77 (11)	C13—C12—H12A	121.0
C5—C4—H4A	120.1	C12—C13—C14	121.49 (12)
C3—C4—H4A	120.1	C12—C13—Cl2	119.03 (11)
C4—C5—C6	121.34 (11)	C14—C13—Cl2	119.48 (11)
C4—C5—H5A	119.3	C15—C14—C13	119.04 (12)
C6—C5—H5A	119.3	C15—C14—H14A	120.5
C1—C6—C5	118.10 (11)	C13—C14—H14A	120.5
C1—C6—C7	123.30 (10)	C14—C15—C10	121.94 (12)
C5—C6—C7	118.60 (10)	C14—C15—H15A	119.0
O1—C7—C6	120.25 (11)	C10—C15—H15A	119.0
O1—C7—C8	120.40 (11)	O2—C16—H16A	109.5
C6—C7—C8	119.35 (10)	O2—C16—H16B	109.5
C9—C8—C7	119.17 (11)	H16A—C16—H16B	109.5
C9—C8—H8A	120.4	O2—C16—H16C	109.5
C7—C8—H8A	120.4	H16A—C16—H16C	109.5
C8—C9—C10	126.97 (11)	H16B—C16—H16C	109.5

C6—C1—C2—C3	−0.03 (18)	C6—C7—C8—C9	−162.05 (12)
C16—O2—C3—C2	−3.65 (19)	C7—C8—C9—C10	179.98 (12)
C16—O2—C3—C4	176.68 (12)	C8—C9—C10—C11	−171.67 (13)
C1—C2—C3—O2	179.96 (12)	C8—C9—C10—C15	8.5 (2)
C1—C2—C3—C4	−0.39 (19)	C15—C10—C11—C12	0.92 (19)
O2—C3—C4—C5	179.99 (12)	C9—C10—C11—C12	−178.91 (13)
C2—C3—C4—C5	0.31 (19)	C15—C10—C11—Cl1	−178.64 (10)
C3—C4—C5—C6	0.2 (2)	C9—C10—C11—Cl1	1.53 (17)
C2—C1—C6—C5	0.51 (18)	C10—C11—C12—C13	0.4 (2)
C2—C1—C6—C7	179.57 (11)	Cl1—C11—C12—C13	−179.98 (11)
C4—C5—C6—C1	−0.60 (18)	C11—C12—C13—C14	−1.5 (2)
C4—C5—C6—C7	−179.70 (12)	C11—C12—C13—Cl2	178.17 (10)
C1—C6—C7—O1	−175.38 (12)	C12—C13—C14—C15	1.2 (2)
C5—C6—C7—O1	3.67 (17)	Cl2—C13—C14—C15	−178.50 (11)
C1—C6—C7—C8	3.89 (17)	C13—C14—C15—C10	0.3 (2)
C5—C6—C7—C8	−177.05 (11)	C11—C10—C15—C14	−1.27 (19)
O1—C7—C8—C9	17.23 (18)	C9—C10—C15—C14	178.55 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1ⁱ	0.93	2.47	3.2695 (15)	143
C9—H9A···Cl1	0.93	2.61	3.0536 (11)	109
C9—H9A···O1	0.93	2.44	2.7840 (15)	101

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

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3-(2,4-Dichloro­phen­yl)-1-(4-methoxyphen­yl)prop-2-en-1-one

Supporting information

Key indicators

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3-(2,4-Dichlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one