1-(4-Chloro­phen­yl)-3-(4-ethoxy­phen­yl)prop-2-en-1-one

Patil, P.S.; Fun, H.-K.; Chantrapromma, S.; Dharmaprakash, S.M.

doi:10.1107/S1600536807017394

1-(4-Chlorophenyl)-3-(4-ethoxyphenyl)prop-2-en-1-one

P. S. Patil, H.-K. Fun, S. Chantrapromma and S. M. Dharmaprakash

The title compound, C₁₇H₁₅ClO₂, crystallizes in a non-centrosymmetric space group and exhibits non-linear optical properties. The molecule exists in an E configuration, with a dihedral angle of 7.44 (9)° between the two benzene rings.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017394/bi2170sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017394/bi2170Isup2.hkl Contains datablock I

CCDC reference: 646730

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.041
wR factor = 0.104
Data-to-parameter ratio = 20.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.34
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.06

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           30.00
           From the CIF: _reflns_number_total               3788
           Count of symmetry unique reflns         2117
           Completeness (_total/calc)            178.93%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1671
           Fraction of Friedel pairs measured     0.789
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   2 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
   1 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: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

1-(4-Chlorophenyl)-3-(4-ethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₇H₁₅ClO₂	F(000) = 300
M_r = 286.74	D_x = 1.382 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3788 reflections
a = 3.9479 (1) Å	θ = 1.2–30.0°
b = 10.1234 (3) Å	µ = 0.28 mm⁻¹
c = 17.2553 (6) Å	T = 100 K
β = 91.823 (2)°	Plate, colourless
V = 689.28 (4) Å³	0.44 × 0.32 × 0.10 mm
Z = 2

Data collection top

Bruker SMART APEX2 CCD diffractometer	3788 independent reflections
Radiation source: fine-focus sealed tube	3336 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ω scans	θ_max = 30.0°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −5→5
T_min = 0.889, T_max = 0.973	k = −14→13
11477 measured reflections	l = −21→24

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.0538P)² + 0.1189P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3788 reflections	Δρ_max = 0.54 e Å⁻³
182 parameters	Δρ_min = −0.23 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1674 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (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	0.42020 (12)	0.11483 (5)	0.00104 (3)	0.03208 (13)
O1	−0.1443 (4)	0.52917 (15)	0.26898 (9)	0.0319 (3)
O2	0.5196 (3)	0.40089 (14)	0.73151 (8)	0.0270 (3)
C1	0.0635 (5)	0.39873 (19)	0.13637 (12)	0.0259 (4)
H1A	−0.0493	0.4789	0.1302	0.031*
C2	0.1462 (5)	0.3270 (2)	0.07149 (12)	0.0255 (4)
H2A	0.0922	0.3586	0.0220	0.031*
C3	0.3116 (5)	0.20672 (19)	0.08166 (12)	0.0242 (4)
C4	0.3944 (5)	0.15839 (19)	0.15434 (11)	0.0246 (4)
H4A	0.5058	0.0779	0.1601	0.029*
C5	0.3095 (5)	0.23128 (19)	0.21890 (12)	0.0240 (4)
H5A	0.3620	0.1985	0.2682	0.029*
C6	0.1458 (5)	0.35349 (19)	0.21098 (11)	0.0225 (4)
C7	0.0470 (5)	0.43489 (19)	0.27902 (12)	0.0252 (4)
C8	0.1838 (5)	0.3997 (2)	0.35679 (12)	0.0269 (4)
H8A	0.3348	0.3296	0.3622	0.032*
C9	0.0948 (5)	0.46689 (19)	0.41984 (12)	0.0255 (4)
H9A	−0.0596	0.5353	0.4117	0.031*
C10	0.2127 (5)	0.44499 (19)	0.49988 (12)	0.0252 (4)
C11	0.4009 (5)	0.33336 (19)	0.52389 (13)	0.0263 (4)
H11A	0.4587	0.2709	0.4870	0.032*
C12	0.5019 (5)	0.31348 (19)	0.59980 (12)	0.0268 (4)
H12A	0.6218	0.2377	0.6139	0.032*
C13	0.4238 (5)	0.40761 (19)	0.65590 (12)	0.0236 (4)
C14	0.2329 (5)	0.51904 (19)	0.63338 (11)	0.0246 (4)
H14A	0.1765	0.5817	0.6702	0.030*
C15	0.1287 (5)	0.5362 (2)	0.55704 (12)	0.0257 (4)
H15A	−0.0002	0.6099	0.5433	0.031*
C16	0.7087 (5)	0.2854 (2)	0.75805 (13)	0.0292 (4)
H16A	0.9039	0.2718	0.7263	0.035*
H16B	0.5666	0.2074	0.7545	0.035*
C17	0.8211 (6)	0.3096 (2)	0.84097 (13)	0.0337 (5)
H17A	0.9578	0.3880	0.8439	0.051*
H17B	0.9514	0.2355	0.8598	0.051*
H17C	0.6259	0.3207	0.8721	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0364 (2)	0.0315 (2)	0.0284 (2)	−0.0010 (2)	0.00127 (17)	−0.0058 (2)
O1	0.0335 (8)	0.0238 (7)	0.0385 (9)	0.0034 (6)	0.0011 (6)	−0.0013 (6)
O2	0.0263 (7)	0.0222 (7)	0.0322 (8)	0.0028 (6)	−0.0033 (5)	−0.0021 (6)
C1	0.0284 (10)	0.0183 (9)	0.0309 (10)	−0.0001 (8)	−0.0012 (8)	0.0013 (8)
C2	0.0297 (10)	0.0220 (9)	0.0245 (9)	−0.0027 (8)	−0.0039 (7)	0.0045 (7)
C3	0.0246 (9)	0.0219 (9)	0.0261 (10)	−0.0041 (7)	−0.0002 (7)	−0.0039 (7)
C4	0.0230 (9)	0.0200 (8)	0.0306 (10)	0.0009 (7)	−0.0015 (7)	0.0011 (7)
C5	0.0261 (9)	0.0218 (9)	0.0239 (10)	−0.0006 (7)	−0.0020 (7)	0.0020 (7)
C6	0.0216 (9)	0.0199 (9)	0.0262 (9)	−0.0042 (7)	0.0015 (7)	0.0001 (7)
C7	0.0258 (9)	0.0204 (9)	0.0297 (10)	−0.0033 (7)	0.0025 (7)	0.0007 (7)
C8	0.0236 (9)	0.0247 (9)	0.0322 (10)	0.0006 (8)	0.0005 (7)	0.0007 (8)
C9	0.0216 (9)	0.0222 (9)	0.0329 (11)	−0.0027 (7)	0.0024 (7)	0.0000 (7)
C10	0.0243 (9)	0.0230 (9)	0.0285 (10)	−0.0046 (7)	0.0035 (7)	−0.0032 (8)
C11	0.0260 (9)	0.0192 (9)	0.0340 (10)	−0.0022 (7)	0.0064 (8)	−0.0049 (8)
C12	0.0233 (9)	0.0202 (9)	0.0369 (11)	−0.0006 (7)	0.0023 (7)	−0.0038 (8)
C13	0.0189 (8)	0.0201 (8)	0.0319 (10)	−0.0037 (7)	0.0015 (7)	−0.0025 (8)
C14	0.0228 (9)	0.0201 (8)	0.0310 (10)	−0.0011 (7)	0.0025 (7)	−0.0064 (7)
C15	0.0235 (9)	0.0194 (9)	0.0344 (11)	−0.0002 (7)	0.0019 (7)	−0.0034 (7)
C16	0.0235 (9)	0.0206 (9)	0.0434 (13)	0.0017 (7)	0.0005 (8)	0.0014 (8)
C17	0.0320 (11)	0.0304 (11)	0.0388 (13)	0.0019 (9)	−0.0001 (9)	0.0077 (9)

Geometric parameters (Å, º) top

Cl1—C3	1.738 (2)	C9—C10	1.460 (3)
O1—C7	1.226 (2)	C9—H9A	0.930
O2—C13	1.348 (2)	C10—C15	1.398 (3)
O2—C16	1.453 (2)	C10—C11	1.407 (3)
C1—C2	1.382 (3)	C11—C12	1.372 (3)
C1—C6	1.395 (3)	C11—H11A	0.930
C1—H1A	0.930	C12—C13	1.400 (3)
C2—C3	1.390 (3)	C12—H12A	0.930
C2—H2A	0.930	C13—C14	1.405 (3)
C3—C4	1.376 (3)	C14—C15	1.379 (3)
C4—C5	1.386 (3)	C14—H14A	0.930
C4—H4A	0.930	C15—H15A	0.930
C5—C6	1.400 (3)	C16—C17	1.505 (3)
C5—H5A	0.930	C16—H16A	0.970
C6—C7	1.496 (3)	C16—H16B	0.970
C7—C8	1.474 (3)	C17—H17A	0.960
C8—C9	1.339 (3)	C17—H17B	0.960
C8—H8A	0.930	C17—H17C	0.960

C13—O2—C16	118.10 (15)	C15—C10—C9	119.42 (18)
C2—C1—C6	121.40 (18)	C11—C10—C9	123.34 (18)
C2—C1—H1A	119.3	C12—C11—C10	122.24 (18)
C6—C1—H1A	119.3	C12—C11—H11A	118.9
C1—C2—C3	118.69 (18)	C10—C11—H11A	118.9
C1—C2—H2A	120.7	C11—C12—C13	119.79 (18)
C3—C2—H2A	120.7	C11—C12—H12A	120.1
C4—C3—C2	121.57 (18)	C13—C12—H12A	120.1
C4—C3—Cl1	118.79 (15)	O2—C13—C12	125.01 (18)
C2—C3—Cl1	119.64 (15)	O2—C13—C14	116.08 (17)
C3—C4—C5	119.13 (18)	C12—C13—C14	118.91 (18)
C3—C4—H4A	120.4	C15—C14—C13	120.44 (18)
C5—C4—H4A	120.4	C15—C14—H14A	119.8
C4—C5—C6	120.96 (18)	C13—C14—H14A	119.8
C4—C5—H5A	119.5	C14—C15—C10	121.37 (18)
C6—C5—H5A	119.5	C14—C15—H15A	119.3
C1—C6—C5	118.25 (17)	C10—C15—H15A	119.3
C1—C6—C7	118.97 (18)	O2—C16—C17	107.59 (17)
C5—C6—C7	122.75 (17)	O2—C16—H16A	110.2
O1—C7—C8	121.52 (19)	C17—C16—H16A	110.2
O1—C7—C6	119.52 (18)	O2—C16—H16B	110.2
C8—C7—C6	118.96 (17)	C17—C16—H16B	110.2
C9—C8—C7	121.27 (19)	H16A—C16—H16B	108.5
C9—C8—H8A	119.4	C16—C17—H17A	109.5
C7—C8—H8A	119.4	C16—C17—H17B	109.5
C8—C9—C10	127.40 (19)	H17A—C17—H17B	109.5
C8—C9—H9A	116.3	C16—C17—H17C	109.5
C10—C9—H9A	116.3	H17A—C17—H17C	109.5
C15—C10—C11	117.21 (18)	H17B—C17—H17C	109.5

C6—C1—C2—C3	0.7 (3)	C7—C8—C9—C10	−178.96 (18)
C1—C2—C3—C4	−0.1 (3)	C8—C9—C10—C15	171.2 (2)
C1—C2—C3—Cl1	−179.71 (15)	C8—C9—C10—C11	−10.8 (3)
C2—C3—C4—C5	0.2 (3)	C15—C10—C11—C12	−0.4 (3)
Cl1—C3—C4—C5	179.82 (15)	C9—C10—C11—C12	−178.41 (18)
C3—C4—C5—C6	−0.9 (3)	C10—C11—C12—C13	−1.4 (3)
C2—C1—C6—C5	−1.3 (3)	C16—O2—C13—C12	−2.2 (3)
C2—C1—C6—C7	−179.45 (17)	C16—O2—C13—C14	178.15 (16)
C4—C5—C6—C1	1.4 (3)	C11—C12—C13—O2	−177.61 (17)
C4—C5—C6—C7	179.47 (18)	C11—C12—C13—C14	2.1 (3)
C1—C6—C7—O1	10.3 (3)	O2—C13—C14—C15	178.74 (17)
C5—C6—C7—O1	−167.77 (18)	C12—C13—C14—C15	−0.9 (3)
C1—C6—C7—C8	−169.50 (18)	C13—C14—C15—C10	−0.9 (3)
C5—C6—C7—C8	12.4 (3)	C11—C10—C15—C14	1.5 (3)
O1—C7—C8—C9	2.3 (3)	C9—C10—C15—C14	179.63 (18)
C6—C7—C8—C9	−177.90 (18)	C13—O2—C16—C17	173.06 (16)

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1-(4-Chloro­phen­yl)-3-(4-ethoxy­phen­yl)prop-2-en-1-one

Supporting information

Key indicators

checkCIF/PLATON results

1-(4-Chlorophenyl)-3-(4-ethoxyphenyl)prop-2-en-1-one