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

Patil, P.S.; Teh, J.B.-J.; Fun, H.-K.; Razak, I.A.; Dharmaprakash, S.M.

doi:10.1107/S1600536806024445

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

P. S. Patil, J. B.-J. Teh, H.-K. Fun, I. A. Razak and S. M. Dharmaprakash

The title compound, C₁₆H₁₂Cl₂O, exhibits second-order nonlinear optical properties as it crystallizes in a non-centrosymmetric space group. The dihedral angle between the benzene rings is 34.02 (6)°. Intermolecular C—H

O interactions link the molecules to form chains along the c axis.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024445/ob2030sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024445/ob2030Isup2.hkl Contains datablock I

CCDC reference: 613792

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.057
wR factor = 0.141
Data-to-parameter ratio = 38.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.10

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           37.50
           From the CIF: _reflns_number_total               6715
           Count of symmetry unique reflns         3662
           Completeness (_total/calc)            183.37%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3053
           Fraction of Friedel pairs measured     0.834
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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-methylphenyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₂Cl₂O	F(000) = 600
M_r = 291.16	D_x = 1.442 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5627 reflections
a = 28.3884 (5) Å	θ = 1.4–37.5°
b = 3.9343 (1) Å	µ = 0.47 mm⁻¹
c = 12.0092 (2) Å	T = 100 K
V = 1341.29 (5) Å³	Slab, yellow
Z = 4	0.51 × 0.43 × 0.08 mm

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	6715 independent reflections
Radiation source: fine-focus sealed tube	6036 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.079
Detector resolution: 8.33 pixels mm^-1	θ_max = 37.5°, θ_min = 1.4°
ω scans	h = −48→48
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→6
T_min = 0.866, T_max = 0.962	l = −20→20
35136 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.141	w = 1/[σ²(F_o²) + (0.058P)² + 0.6516P] where P = (F_o² + 2F_c²)/3
S = 1.18	(Δ/σ)_max < 0.001
6715 reflections	Δρ_max = 0.70 e Å⁻³
173 parameters	Δρ_min = −0.39 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 3071 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (6)

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

	x	y	z	U_iso*/U_eq
Cl1	1.028068 (17)	−0.04137 (12)	0.28715 (4)	0.02009 (9)
Cl2	1.170897 (16)	−0.05706 (14)	0.57625 (5)	0.02492 (11)
O1	0.88511 (6)	0.5904 (5)	0.38658 (15)	0.0297 (4)
C1	0.86014 (7)	0.6214 (5)	0.68107 (17)	0.0176 (3)
H1A	0.8867	0.5107	0.7083	0.021*
C2	0.82355 (6)	0.7047 (5)	0.75324 (18)	0.0180 (3)
H2A	0.8256	0.6440	0.8279	0.022*
C3	0.78358 (7)	0.8787 (5)	0.71508 (18)	0.0177 (3)
C4	0.78150 (7)	0.9629 (5)	0.60185 (18)	0.0201 (3)
H4A	0.7555	1.0805	0.5748	0.024*
C5	0.81740 (7)	0.8747 (5)	0.52932 (17)	0.0184 (3)
H5A	0.8150	0.9301	0.4543	0.022*
C6	0.85724 (6)	0.7029 (5)	0.56826 (16)	0.0158 (3)
C7	0.89410 (7)	0.6021 (5)	0.48688 (17)	0.0185 (3)
C8	0.94186 (7)	0.5123 (5)	0.52898 (17)	0.0177 (3)
H8A	0.9501	0.5635	0.6020	0.021*
C9	0.97318 (6)	0.3575 (5)	0.46182 (16)	0.0169 (3)
H9A	0.9632	0.3070	0.3899	0.020*
C10	1.02146 (6)	0.2611 (5)	0.49129 (15)	0.0139 (3)
C11	1.04970 (6)	0.0798 (5)	0.41684 (15)	0.0149 (3)
C12	1.09584 (7)	−0.0177 (4)	0.44134 (18)	0.0160 (3)
H12A	1.1138	−0.1378	0.3900	0.019*
C13	1.11414 (7)	0.0702 (5)	0.54481 (17)	0.0172 (3)
C14	1.08788 (6)	0.2524 (5)	0.62215 (17)	0.0174 (3)
H14A	1.1005	0.3095	0.6911	0.021*
C15	1.04222 (6)	0.3473 (5)	0.59390 (16)	0.0161 (3)
H15A	1.0247	0.4728	0.6449	0.019*
C16	0.74457 (7)	0.9796 (5)	0.7945 (2)	0.0216 (3)
H16A	0.7359	1.2121	0.7814	0.032*
H16B	0.7554	0.9546	0.8698	0.032*
H16C	0.7177	0.8360	0.7826	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02310 (19)	0.02187 (19)	0.01530 (17)	0.00012 (15)	−0.00145 (15)	−0.00414 (18)
Cl2	0.01720 (18)	0.0264 (2)	0.0312 (3)	0.00085 (16)	−0.00458 (18)	0.0007 (2)
O1	0.0279 (8)	0.0457 (10)	0.0156 (7)	0.0093 (7)	−0.0009 (5)	0.0002 (7)
C1	0.0165 (7)	0.0182 (7)	0.0180 (8)	0.0019 (6)	−0.0018 (6)	−0.0004 (6)
C2	0.0162 (7)	0.0220 (8)	0.0160 (7)	−0.0019 (6)	−0.0009 (6)	−0.0008 (6)
C3	0.0174 (7)	0.0151 (7)	0.0206 (8)	−0.0006 (6)	−0.0009 (6)	−0.0034 (6)
C4	0.0191 (8)	0.0204 (8)	0.0208 (9)	0.0025 (6)	−0.0035 (6)	−0.0008 (7)
C5	0.0205 (8)	0.0177 (7)	0.0169 (8)	0.0014 (6)	−0.0027 (6)	0.0005 (6)
C6	0.0157 (6)	0.0167 (7)	0.0151 (7)	−0.0009 (5)	−0.0008 (5)	0.0007 (6)
C7	0.0193 (7)	0.0194 (8)	0.0166 (8)	0.0008 (6)	−0.0006 (6)	0.0009 (6)
C8	0.0175 (7)	0.0189 (8)	0.0168 (8)	0.0020 (6)	−0.0010 (6)	0.0001 (6)
C9	0.0167 (7)	0.0185 (7)	0.0156 (7)	0.0001 (6)	0.0006 (6)	0.0013 (6)
C10	0.0135 (6)	0.0148 (7)	0.0135 (7)	−0.0028 (5)	0.0000 (5)	0.0005 (5)
C11	0.0181 (7)	0.0131 (7)	0.0135 (7)	−0.0033 (5)	0.0000 (5)	0.0010 (5)
C12	0.0158 (7)	0.0130 (6)	0.0192 (8)	−0.0017 (5)	0.0017 (5)	−0.0011 (6)
C13	0.0146 (7)	0.0163 (7)	0.0205 (8)	−0.0039 (6)	−0.0016 (5)	0.0030 (6)
C14	0.0170 (7)	0.0194 (8)	0.0157 (7)	−0.0043 (6)	−0.0015 (6)	−0.0002 (6)
C15	0.0167 (7)	0.0174 (7)	0.0141 (7)	−0.0031 (6)	0.0007 (5)	−0.0001 (6)
C16	0.0192 (7)	0.0208 (8)	0.0248 (9)	0.0036 (6)	0.0037 (7)	−0.0030 (7)

Geometric parameters (Å, º) top

Cl1—C11	1.7407 (19)	C8—C9	1.346 (3)
Cl2—C13	1.729 (2)	C8—H8A	0.9300
O1—C7	1.232 (3)	C9—C10	1.466 (3)
C1—C2	1.392 (3)	C9—H9A	0.9300
C1—C6	1.395 (3)	C10—C11	1.397 (3)
C1—H1A	0.9300	C10—C15	1.408 (3)
C2—C3	1.402 (3)	C11—C12	1.396 (3)
C2—H2A	0.9300	C12—C13	1.390 (3)
C3—C4	1.401 (3)	C12—H12A	0.9300
C3—C16	1.514 (3)	C13—C14	1.390 (3)
C4—C5	1.385 (3)	C14—C15	1.391 (3)
C4—H4A	0.9300	C14—H14A	0.9300
C5—C6	1.398 (3)	C15—H15A	0.9300
C5—H5A	0.9300	C16—H16A	0.9600
C6—C7	1.486 (3)	C16—H16B	0.9600
C7—C8	1.489 (3)	C16—H16C	0.9600

C2—C1—C6	120.44 (18)	C10—C9—H9A	116.9
C2—C1—H1A	119.8	C11—C10—C15	116.31 (16)
C6—C1—H1A	119.8	C11—C10—C9	120.95 (16)
C1—C2—C3	121.03 (19)	C15—C10—C9	122.73 (17)
C1—C2—H2A	119.5	C12—C11—C10	122.94 (17)
C3—C2—H2A	119.5	C12—C11—Cl1	116.38 (15)
C4—C3—C2	117.83 (19)	C10—C11—Cl1	120.68 (14)
C4—C3—C16	121.22 (19)	C13—C12—C11	118.07 (17)
C2—C3—C16	120.93 (19)	C13—C12—H12A	121.0
C5—C4—C3	121.35 (18)	C11—C12—H12A	121.0
C5—C4—H4A	119.3	C14—C13—C12	121.67 (17)
C3—C4—H4A	119.3	C14—C13—Cl2	120.21 (15)
C4—C5—C6	120.41 (19)	C12—C13—Cl2	118.12 (15)
C4—C5—H5A	119.8	C13—C14—C15	118.38 (18)
C6—C5—H5A	119.8	C13—C14—H14A	120.8
C1—C6—C5	118.94 (18)	C15—C14—H14A	120.8
C1—C6—C7	122.41 (16)	C14—C15—C10	122.62 (17)
C5—C6—C7	118.61 (18)	C14—C15—H15A	118.7
O1—C7—C6	120.47 (19)	C10—C15—H15A	118.7
O1—C7—C8	120.76 (19)	C3—C16—H16A	109.5
C6—C7—C8	118.76 (17)	C3—C16—H16B	109.5
C9—C8—C7	120.34 (18)	H16A—C16—H16B	109.5
C9—C8—H8A	119.8	C3—C16—H16C	109.5
C7—C8—H8A	119.8	H16A—C16—H16C	109.5
C8—C9—C10	126.16 (18)	H16B—C16—H16C	109.5
C8—C9—H9A	116.9

C6—C1—C2—C3	−1.5 (3)	C7—C8—C9—C10	178.71 (18)
C1—C2—C3—C4	0.6 (3)	C8—C9—C10—C11	175.48 (19)
C1—C2—C3—C16	−177.90 (19)	C8—C9—C10—C15	−5.4 (3)
C2—C3—C4—C5	0.7 (3)	C15—C10—C11—C12	0.8 (3)
C16—C3—C4—C5	179.17 (19)	C9—C10—C11—C12	−179.94 (17)
C3—C4—C5—C6	−1.0 (3)	C15—C10—C11—Cl1	−179.94 (13)
C2—C1—C6—C5	1.1 (3)	C9—C10—C11—Cl1	−0.7 (2)
C2—C1—C6—C7	−176.46 (18)	C10—C11—C12—C13	0.2 (3)
C4—C5—C6—C1	0.1 (3)	Cl1—C11—C12—C13	−179.08 (14)
C4—C5—C6—C7	177.81 (18)	C11—C12—C13—C14	−0.6 (3)
C1—C6—C7—O1	159.5 (2)	C11—C12—C13—Cl2	178.84 (14)
C5—C6—C7—O1	−18.1 (3)	C12—C13—C14—C15	0.0 (3)
C1—C6—C7—C8	−19.9 (3)	Cl2—C13—C14—C15	−179.45 (14)
C5—C6—C7—C8	162.52 (18)	C13—C14—C15—C10	1.1 (3)
O1—C7—C8—C9	−12.4 (3)	C11—C10—C15—C14	−1.5 (3)
C6—C7—C8—C9	166.95 (18)	C9—C10—C15—C14	179.30 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···Cl1	0.93	2.61	3.048 (2)	110
C9—H9A···O1	0.93	2.48	2.812 (2)	101
C14—H14A···O1ⁱ	0.93	2.42	3.325 (3)	166

Symmetry code: (i) −x+2, −y+1, z+1/2.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Supporting information

Key indicators

checkCIF/PLATON results

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