1-(3,4-Di­meth­oxy­phen­yl)-3-phenyl­prop-2-en-1-one

Umesha, B.; Basavaraju, Y.B.; Kaur, M.; Yathirajan, H.S.; Jasinski, J.P.

doi:10.1107/S160053681400378X

organic compounds

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ISSN: 2056-9890

Volume 70| Part 3| March 2014| Page o368

doi:10.1107/S160053681400378X

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1-(3,4-Dimethoxyphenyl)-3-phenylprop-2-en-1-one

Basavaiah Umesha,^a Yeriyur Basavaiah Basavaraju,^a Manpreet Kaur,^a Hemmige S. Yathirajan ^a and Jerry P. Jasinski ^b ^*

^aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
^*Correspondence e-mail: jjasinski@keene.edu

(Received 14 February 2014; accepted 18 February 2014; online 28 February 2014)

In the title compound, C₁₇H₁₆O₃, the dihedral angle between the mean planes of the benzene rings is 57.1 (1)°. The mean plane of the ketone group is twisted by 10.0 (5)° from that of the dimethoxyphenyl ring. The two dimethoxyphenyl groups are twisted slighly from the mean plane of the phenyl ring, with C—O—C—C torsion angles of 6.4 (2) and −7.9 (2)° [r.m.s. deviations = 0.15 (3) and 0.18 (3) Å for the two methoxy C atoms]. In the crystal, weak centroid–centroid π–π stacking interactions, with intercentroid distances of 3.8939 (11) and 3.9430 (10) Å are observed.

CCDC reference: 987727

Related literature

For applications of the title compound as an intermediate in the synthesis of pyrazole derivatives, which have pharmaceutical applications, see: Basavaraju & Devaraju (2002 ). For applications of chalcone derivatives in biological studies, see: Choudhary & Juyal (2011 ). For applications of chalcone derivatives for their blue-light transmittance, see: Uchida et al. (1998 ). For the synthesis, see: Umesha & Basavaraju (2013 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₇H₁₆O₃
M_r = 268.30
Triclinic, $[P \overline 1]$
a = 7.3269 (7) Å
b = 9.8923 (11) Å
c = 10.7668 (11) Å
α = 102.408 (9)°
β = 109.255 (9)°
γ = 98.951 (9)°
V = 697.48 (13) Å³
Z = 2
Cu Kα radiation
μ = 0.70 mm⁻¹
T = 173 K
0.36 × 0.28 × 0.16 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ) T_min = 0.842, T_max = 1.000
4094 measured reflections
2671 independent reflections
2261 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.152
S = 1.05
2671 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ; Palatinus & van der Lee, 2008 ; Palatinus et al., 2012 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 987727

Crystal structure: contains datablock I. DOI: 10.1107/S160053681400378X/bt6962sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681400378X/bt6962Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681400378X/bt6962Isup3.cml

checkCIF report

Comment top

1-(3,4-dimethoxyphenyl)-3-phenylprop-2-en-1-one is an intermediate for the synthesis of pyrazole derivatives, podophyllotoxin and its derivatives which have pharmaceutical applications (Basavaraju & Devaraju, 2002). More generally, chalcone derivatives have many applications in biological studies (Choudhary & Juyal, 2011). Chalcone derivatives are notable for their excellent blue-light transmittance and good crystallizability (Uchida et al., 1998). In continuation of our work on chalcone derivatives, this paper reports the crystal structure of the title compound C₁₇H₁₆O₃.

In the title compound the dihedral angle between the mean planes of the two phenyl rings is 57.1 (1)° (Fig. 1). The mean plane of the ketone group (C2/C1/O1/C10) is twisted by 10.0 (5)° from that of the dimethoxyphenyl ring. The two dimethoxyphenyl groups are twisted slighly from the mean plane of the phenyl ring with torsion angles of 6.4 (2)° (C16/O2/C14/C15) and -7.9 (2)° (C17/O3/C13/C12) [r.m.s. deviations = 0.15 (3) and 0.18 (3)Å for the two methoxy C atoms]. Bond lengths are in normal ranges (Allen et al., 1987). In the crystal, while no classical hydrogen bonds are observed, weak Cg1–Cg1 and Cg2–Cg2 π–π stacking interactions with intercentroid distances of 3.8939 (11) Å and 3.9430 (10) Å (Symmetry operations 1 - x, 2 - y, 1 - z and -x, 1 - y, 2 - z; Cg1 and Cg2 are the centroids of the phenyl rings, C4–C9 and C10–C15) between the phenyl rings are observed and contribute to the crystal packing.

Related literature top

For applications of the title compound as an intermediate in the synthesis of pyrazole derivatives, podophyllotoxin and its derivatives which have pharmaceutical applications, see: Basavaraju & Devaraju (2002). For applications of chalcone derivatives in biological studies, see: Choudhary & Juyal (2011). For applications of chalcone derivatives for their blue-light transmittance and crystallizability properties, see: Uchida et al. (1998). For the synthesis of (I), see: Umesha & Basavaraju (2013). For standard bond lengths, see: Allen et al. (1987).

Experimental top

1-(3,4-Dimethoxyphenyl)ethanone (1.80 g 10 mmol) and benzaldehyde (1.02 ml, 10 mmol) were stirred in water (40 ml) and ethanol (20 ml) mixture in the presence of sodium hydroxide (0.8 g, 20 mmol) at 288–303 K for 4 h (Fig. 2). The reaction mixture was kept overnight in an ice bath. The precipitated products were filtered and recrystallized from methanol. Anal. calcd. for C₁₇H₁₆O₃: C, 76.10; H, 6.01. Found: C, 76.04; H, 5.89% (Umesha & Basavaraju, 2013).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007; Palatinus & van der Lee, 2008; Palatinus et al., 2012); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. ORTEP drawing of (I), C₁₇H₁₆O₃, showing the labeling scheme with 50% probability displacement ellipsoids.
	Fig. 2. The formation of the title compound.

1-(3,4-Dimethoxyphenyl)-3-phenylprop-2-en-1-one top

Crystal data top

C₁₇H₁₆O₃	Z = 2
M_r = 268.30	F(000) = 284
Triclinic, P1	D_x = 1.278 Mg m⁻³
a = 7.3269 (7) Å	Cu Kα radiation, λ = 1.54184 Å
b = 9.8923 (11) Å	Cell parameters from 1960 reflections
c = 10.7668 (11) Å	θ = 4.5–72.3°
α = 102.408 (9)°	µ = 0.70 mm⁻¹
β = 109.255 (9)°	T = 173 K
γ = 98.951 (9)°	Irregular, orange
V = 697.48 (13) Å³	0.36 × 0.28 × 0.16 mm

Data collection top

Agilent Xcalibur (Eos, Gemini) diffractometer	2671 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2261 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 16.0416 pixels mm^-1	θ_max = 72.4°, θ_min = 4.5°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −11→12
T_min = 0.842, T_max = 1.000	l = −12→13
4094 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.051	w = 1/[σ²(F_o²) + (0.0909P)² + 0.0371P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.152	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.30 e Å⁻³
2671 reflections	Δρ_min = −0.20 e Å⁻³
184 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.016 (3)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₇H₁₆O₃	γ = 98.951 (9)°
M_r = 268.30	V = 697.48 (13) Å³
Triclinic, P1	Z = 2
a = 7.3269 (7) Å	Cu Kα radiation
b = 9.8923 (11) Å	µ = 0.70 mm⁻¹
c = 10.7668 (11) Å	T = 173 K
α = 102.408 (9)°	0.36 × 0.28 × 0.16 mm
β = 109.255 (9)°

Data collection top

Agilent Xcalibur (Eos, Gemini) diffractometer	2671 independent reflections
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	2261 reflections with I > 2σ(I)
T_min = 0.842, T_max = 1.000	R_int = 0.034
4094 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.05	Δρ_max = 0.30 e Å⁻³
2671 reflections	Δρ_min = −0.20 e Å⁻³
184 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.1915 (2)	0.40453 (12)	0.63226 (11)	0.0458 (4)
O2	0.11843 (19)	0.13233 (12)	0.97010 (11)	0.0408 (3)
O3	0.17608 (19)	0.32198 (13)	1.19243 (11)	0.0412 (3)
C1	0.2507 (2)	0.49627 (17)	0.74331 (15)	0.0340 (4)
C2	0.3317 (2)	0.64736 (17)	0.75594 (16)	0.0354 (4)
H2	0.4221	0.7092	0.8425	0.042*
C3	0.2797 (2)	0.69778 (17)	0.64760 (15)	0.0349 (4)
H3	0.1903	0.6322	0.5627	0.042*
C4	0.3472 (2)	0.84500 (16)	0.64690 (15)	0.0335 (4)
C5	0.2255 (3)	0.89601 (17)	0.54684 (16)	0.0379 (4)
H5	0.1058	0.8340	0.4781	0.046*
C6	0.2791 (3)	1.03693 (18)	0.54759 (17)	0.0426 (4)
H6	0.1942	1.0718	0.4806	0.051*
C7	0.4548 (3)	1.12685 (18)	0.64490 (18)	0.0439 (4)
H7	0.4906	1.2234	0.6450	0.053*
C8	0.5793 (3)	1.07642 (18)	0.74269 (17)	0.0423 (4)
H8	0.7013	1.1381	0.8089	0.051*
C9	0.5262 (2)	0.93635 (17)	0.74404 (16)	0.0375 (4)
H9	0.6118	0.9022	0.8113	0.045*
C10	0.2372 (2)	0.45707 (16)	0.86635 (15)	0.0315 (4)
C11	0.2692 (2)	0.55923 (17)	0.98761 (16)	0.0349 (4)
H11	0.3050	0.6579	0.9945	0.042*
C12	0.2489 (2)	0.51738 (17)	1.09853 (15)	0.0361 (4)
H12	0.2698	0.5877	1.1807	0.043*
C13	0.1986 (2)	0.37465 (17)	1.09029 (15)	0.0335 (4)
C14	0.1668 (2)	0.26993 (17)	0.96737 (15)	0.0322 (4)
C15	0.1855 (2)	0.31230 (16)	0.85772 (14)	0.0318 (4)
H15	0.1630	0.2423	0.7750	0.038*
C16	0.1048 (3)	0.02320 (18)	0.85413 (17)	0.0456 (5)
H16A	−0.0049	0.0246	0.7726	0.068*
H16B	0.0797	−0.0701	0.8711	0.068*
H16C	0.2303	0.0402	0.8391	0.068*
C17	0.2323 (3)	0.4222 (2)	1.32445 (16)	0.0475 (5)
H17A	0.1481	0.4902	1.3175	0.071*
H17B	0.3723	0.4738	1.3562	0.071*
H17C	0.2151	0.3711	1.3899	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0689 (9)	0.0374 (6)	0.0314 (6)	0.0090 (6)	0.0214 (6)	0.0095 (5)
O2	0.0594 (8)	0.0336 (6)	0.0330 (6)	0.0083 (5)	0.0237 (5)	0.0092 (5)
O3	0.0523 (7)	0.0461 (7)	0.0281 (6)	0.0104 (5)	0.0194 (5)	0.0106 (5)
C1	0.0356 (8)	0.0368 (8)	0.0314 (8)	0.0102 (6)	0.0135 (6)	0.0106 (6)
C2	0.0359 (8)	0.0376 (9)	0.0319 (8)	0.0070 (6)	0.0134 (6)	0.0092 (6)
C3	0.0385 (8)	0.0343 (8)	0.0316 (7)	0.0085 (6)	0.0145 (6)	0.0068 (6)
C4	0.0388 (8)	0.0342 (8)	0.0310 (7)	0.0108 (6)	0.0173 (6)	0.0085 (6)
C5	0.0416 (9)	0.0390 (9)	0.0313 (8)	0.0092 (7)	0.0124 (6)	0.0088 (6)
C6	0.0504 (10)	0.0417 (9)	0.0383 (9)	0.0158 (7)	0.0152 (7)	0.0156 (7)
C7	0.0540 (10)	0.0326 (8)	0.0486 (9)	0.0113 (7)	0.0233 (8)	0.0116 (7)
C8	0.0388 (9)	0.0385 (9)	0.0432 (9)	0.0048 (7)	0.0130 (7)	0.0060 (7)
C9	0.0377 (9)	0.0390 (9)	0.0362 (8)	0.0109 (7)	0.0133 (7)	0.0117 (6)
C10	0.0305 (7)	0.0362 (8)	0.0285 (7)	0.0090 (6)	0.0117 (6)	0.0090 (6)
C11	0.0351 (8)	0.0332 (8)	0.0340 (8)	0.0060 (6)	0.0128 (6)	0.0068 (6)
C12	0.0373 (8)	0.0386 (9)	0.0287 (7)	0.0085 (7)	0.0131 (6)	0.0017 (6)
C13	0.0330 (8)	0.0409 (8)	0.0271 (7)	0.0084 (6)	0.0132 (6)	0.0085 (6)
C14	0.0317 (8)	0.0356 (8)	0.0288 (7)	0.0077 (6)	0.0116 (6)	0.0084 (6)
C15	0.0325 (8)	0.0362 (8)	0.0254 (7)	0.0081 (6)	0.0111 (6)	0.0060 (6)
C16	0.0664 (12)	0.0332 (8)	0.0426 (9)	0.0097 (8)	0.0303 (9)	0.0079 (7)
C17	0.0549 (11)	0.0619 (11)	0.0258 (8)	0.0141 (9)	0.0185 (7)	0.0078 (7)

Geometric parameters (Å, º) top

O1—C1	1.2290 (18)	C8—H8	0.9500
O2—C14	1.3613 (19)	C8—C9	1.384 (2)
O2—C16	1.4282 (18)	C9—H9	0.9500
O3—C13	1.3592 (18)	C10—C11	1.392 (2)
O3—C17	1.4331 (19)	C10—C15	1.398 (2)
C1—C2	1.479 (2)	C11—H11	0.9500
C1—C10	1.487 (2)	C11—C12	1.389 (2)
C2—H2	0.9500	C12—H12	0.9500
C2—C3	1.331 (2)	C12—C13	1.378 (2)
C3—H3	0.9500	C13—C14	1.418 (2)
C3—C4	1.466 (2)	C14—C15	1.375 (2)
C4—C5	1.396 (2)	C15—H15	0.9500
C4—C9	1.397 (2)	C16—H16A	0.9800
C5—H5	0.9500	C16—H16B	0.9800
C5—C6	1.386 (2)	C16—H16C	0.9800
C6—H6	0.9500	C17—H17A	0.9800
C6—C7	1.378 (3)	C17—H17B	0.9800
C7—H7	0.9500	C17—H17C	0.9800
C7—C8	1.387 (2)

C14—O2—C16	117.05 (12)	C11—C10—C15	119.33 (14)
C13—O3—C17	117.20 (13)	C15—C10—C1	118.37 (13)
O1—C1—C2	120.69 (14)	C10—C11—H11	119.9
O1—C1—C10	120.23 (14)	C12—C11—C10	120.20 (15)
C2—C1—C10	119.06 (13)	C12—C11—H11	119.9
C1—C2—H2	119.6	C11—C12—H12	119.7
C3—C2—C1	120.82 (14)	C13—C12—C11	120.51 (14)
C3—C2—H2	119.6	C13—C12—H12	119.7
C2—C3—H3	116.9	O3—C13—C12	125.41 (14)
C2—C3—C4	126.11 (14)	O3—C13—C14	114.96 (14)
C4—C3—H3	116.9	C12—C13—C14	119.63 (14)
C5—C4—C3	118.50 (14)	O2—C14—C13	114.95 (13)
C5—C4—C9	119.08 (15)	O2—C14—C15	125.58 (14)
C9—C4—C3	122.41 (14)	C15—C14—C13	119.47 (14)
C4—C5—H5	119.9	C10—C15—H15	119.6
C6—C5—C4	120.12 (15)	C14—C15—C10	120.86 (14)
C6—C5—H5	119.9	C14—C15—H15	119.6
C5—C6—H6	119.8	O2—C16—H16A	109.5
C7—C6—C5	120.37 (16)	O2—C16—H16B	109.5
C7—C6—H6	119.8	O2—C16—H16C	109.5
C6—C7—H7	120.0	H16A—C16—H16B	109.5
C6—C7—C8	120.02 (16)	H16A—C16—H16C	109.5
C8—C7—H7	120.0	H16B—C16—H16C	109.5
C7—C8—H8	119.9	O3—C17—H17A	109.5
C9—C8—C7	120.13 (16)	O3—C17—H17B	109.5
C9—C8—H8	119.9	O3—C17—H17C	109.5
C4—C9—H9	119.9	H17A—C17—H17B	109.5
C8—C9—C4	120.23 (15)	H17A—C17—H17C	109.5
C8—C9—H9	119.9	H17B—C17—H17C	109.5
C11—C10—C1	122.28 (14)

O1—C1—C2—C3	24.6 (2)	C5—C6—C7—C8	0.1 (3)
O1—C1—C10—C11	−168.54 (15)	C6—C7—C8—C9	−0.9 (3)
O1—C1—C10—C15	9.7 (2)	C7—C8—C9—C4	0.1 (3)
O2—C14—C15—C10	−179.58 (14)	C9—C4—C5—C6	−2.3 (2)
O3—C13—C14—O2	0.0 (2)	C10—C1—C2—C3	−153.98 (15)
O3—C13—C14—C15	179.85 (13)	C10—C11—C12—C13	0.5 (2)
C1—C2—C3—C4	179.22 (14)	C11—C10—C15—C14	−0.3 (2)
C1—C10—C11—C12	178.00 (14)	C11—C12—C13—O3	179.57 (15)
C1—C10—C15—C14	−178.63 (13)	C11—C12—C13—C14	−0.2 (2)
C2—C1—C10—C11	10.0 (2)	C12—C13—C14—O2	179.81 (14)
C2—C1—C10—C15	−171.68 (13)	C12—C13—C14—C15	−0.4 (2)
C2—C3—C4—C5	−154.28 (17)	C13—C14—C15—C10	0.6 (2)
C2—C3—C4—C9	24.4 (2)	C15—C10—C11—C12	−0.3 (2)
C3—C4—C5—C6	176.43 (15)	C16—O2—C14—C13	−173.81 (14)
C3—C4—C9—C8	−177.18 (15)	C16—O2—C14—C15	6.4 (2)
C4—C5—C6—C7	1.5 (3)	C17—O3—C13—C12	−7.9 (2)
C5—C4—C9—C8	1.5 (2)	C17—O3—C13—C14	171.84 (14)

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆O₃
M_r	268.30
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.3269 (7), 9.8923 (11), 10.7668 (11)
α, β, γ (°)	102.408 (9), 109.255 (9), 98.951 (9)
V (Å³)	697.48 (13)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.70
Crystal size (mm)	0.36 × 0.28 × 0.16

Data collection
Diffractometer	Agilent Xcalibur (Eos, Gemini) diffractometer
Absorption correction	Multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)
T_min, T_max	0.842, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4094, 2671, 2261
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.152, 1.05
No. of reflections	2671
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.20

Computer programs: CrysAlis PRO (Agilent, 2012), CrysAlis RED (Agilent, 2012), SUPERFLIP (Palatinus & Chapuis, 2007; Palatinus & van der Lee, 2008; Palatinus et al., 2012), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

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