A monoclinic polymorph of 1-(4-chloro­phen­yl)-3-(4-methoxy­phen­yl)prop-2-en-1-one

Jasinski, J.P.; Butcher, R.J.; Narayana, B.; Samshuddin, S.; Yathirajan, H.S.

doi:10.1107/S1600536809054956

organic compounds

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Volume 66| Part 2| February 2010| Pages o269-o270

https://doi.org/10.1107/S1600536809054956

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A monoclinic polymorph of 1-(4-chlorophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one

Jerry P. Jasinski,^a ^* Ray J. Butcher,^b B. Narayana,^c S. Samshuddin ^c and H. S. Yathirajan ^d

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, ^cDepartment of Studies in Chemistry, Mangalore University, Manalaganotri 574 199, India, and ^dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 5 December 2009; accepted 21 December 2009; online 9 January 2010)

The crystal structure of the title compound, C₁₆H₁₃ClO₂ (II), (space group P2₁/c,) is a polymorph of the structure, (I), reported by Harrison, Yathirajan, Sarojini, Narayana & Indira [Acta Cryst. (2006), E62, o1647–o1649] in the orthorhombic space group Pna2₁. The dihedral angle between the mean planes of the 4-chloro- and 4-methoxy-substituted benzene rings is 52.9 (1)° in (II) compared to 21.82 (6)° for polymorph (I). The dihedral angles between the mean planes of the prop-2-en-1-one group and those of the 4-chlorophenyl and 4-methoxyphenyl rings are 23.3 (3) and 33.7 (1)°, respectively. in (II). The corresponding values are 17.7 (1) and 6.0 (3)°, respectively, in polymorph (I). In the crystal, weak C—H⋯π interactions are observed.

Related literature

For the orthorhomic polymorph, see: Harrison et al. (2006 ). For the biological activity of chalcones and flavonoids, see: Dimmock et al. (1999 ); Opletalova & Sedivy (1999 ); Lin et al. (2002 ); Nowakowska (2007 ). For the synthesis and biological activity of some fluorinated chalcone derivatives, see: Nakamura et al. (2002 ). For non-linear optical studies of chalcones and their derivatives, see: Sarojini et al. (2006 ); Poornesh et al. (2009 ); Shettigar et al. (2006 , 2008 ). For our studies of chalcones, see: Jasinski et al. (2009 ).

Experimental

Crystal data

C₁₆H₁₃ClO₂
M_r = 272.71
Monoclinic, P 2₁ /c
a = 15.6695 (7) Å
b = 14.1235 (8) Å
c = 5.8455 (3) Å
β = 90.771 (5)°
V = 1293.53 (12) Å³
Z = 4
Cu Kα radiation
μ = 2.57 mm⁻¹
T = 110 K
0.54 × 0.13 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.483, T_max = 0.558
5083 measured reflections
2537 independent reflections
2223 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.096
S = 1.04
2537 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg1ⁱ	0.95	2.85	3.4675 (15)	124
C12—H12⋯Cg2ⁱⁱ	0.95	2.92	3.6616 (17)	136
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809054956/om2306sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809054956/om2306Isup2.hkl

checkCIF report

Comment top

Chalcone is an unique template molecule that is associated with several biological activities. A review on the bioactivities of chalcones is described (Dimmock et al. 1999). Chalcones and their heterocyclic analogs as potential antifungal chemotherapeutic agents is published (Opletalova & Sedivy, 1999). Chalcones and flavonoids as anti-tuberculosis agents has been reported (Lin et al. 2002) and a review of anti-infective and anti-inflammatory chalcones is also described (Nowakowska, 2007) as well as the synthesis and biological activities of some fluorinated chalcone derivatives (Nakamura et al. 2002). In addition, chalcones are finding applications as organic non-linear optical materials (NLO) due to their good SHG conversion efficiencies (Sarojini et al. 2006). Recently, non-linear optical studies on a few chalcones and their derivatives were reported (Poornesh et al. 2009; Shettigar et al. 2006; 2008). In continuation of our work on chalcones (Jasinski et al. 2009) and in view of the importance of chloro chalcones, this paper describes a new polymorphic form of (I), C₁₆H₁₃ClO₂, 1-(4-chlorophenyl)-3-(4-methoxyphenyl)-prop-2-en-1-one, first reported by Harrison et al. (2006). Substantial changes in the cell parameters provides solid support for the recognition of this new polymorphic form for (I).

The title compound, (II), is a chalcone derivative with 4-chlorophenyl and 4-methoxyphenyl rings bonded at the opposite ends of a propenone group, the biologically active region (Fig.1). The dihedral angle between mean planes of the 4-chloro and 4-methoxy substituted benzene rings in (II) is 52.9 (1)° compared to 21.82 (6)° (Harrison et al. (2006); 4-chlorohenyl & 4-methoxyphenyl) for polymorph (I) in the orthorhombic, Pna2₁, space group. The angles between the mean plane of the prop-2-ene-1-one group and those of the 4-chlorophenyl and 4-methoxyphenyl rings in (II) are 23.3 (3)° and 33.7 (1)°, respectively. This compares to 17.7 (1)° and 6.0 (3)° in polymorph (I). A weak intramolecular C9–H9···O1 hydrogen bond interaction is present which may help to maintain the molecular conformation of the molecule (Table 1) and similar to that observed in (I). While no classical hydrogen bonds are present, weak intermolecular C–H···Cg π-ring interactions are observed, Cg1 = C1–C6 and Cg2 = C10–C15, see Table 1.

Related literature top

Forthe orthorhomic polymorph, see: Harrison et al. (2006). For the biological activity of chalcones and flavonoids, see: Dimmock et al. (1999); Opletalova & Sedivy, (1999); Lin et al. (2002); Nowakowska, (2007). For the synthesis and biological activity of some fluorinated chalcone derivatives, see: Nakamura et al. (2002). For non-linear optical studies of chalcones and their derivatives, see: Sarojini et al. (2006); Poornesh et al. (2009); Shettigar et al. (2006, 2008). For our studies of chalcones, see: Jasinski et al. (2009).

Experimental top

In (II), 4-chloroacetophenone in ethanol (1.54 g, 0.01 mol) (25 ml) was mixed with 4-methoxybenzaldehyde (1.36 g, 0.01 mol) in ethanol (25 ml) and the mixture was treated with an aqueous solution of potassium hydroxide (20 ml, 5%). This mixture was stirred well and left to stand for 24 hr. The resulting crude solid mass was collected by filtration and recrystallized from ethanol, yielding clear blocks of (II). Yield: 90%, m.p.: 391–393 K, analysis found (calculated) for C₁₆H₁₃ClO₂: C: 70.5 (70.4%); H: 4.72 (4.76%). The preparation and crystallization procedure for (I) was identical to that described above for (II). However, in (I) the m.p. measured 380 K, a difference of 12 K. The samples of (I) and (II) were not independently tested for concomitant polymorphism.

Structure description top

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, C₁₆H₁₃ClO₂, (II), showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound, (II), viewed down the c axis. Weak C–H..O intramolecular hydrogen bond interactions are shown as dashed lines.

1-(4-chlorophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₃ClO₂	F(000) = 568
M_r = 272.71	D_x = 1.400 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 3121 reflections
a = 15.6695 (7) Å	θ = 4.2–73.8°
b = 14.1235 (8) Å	µ = 2.57 mm⁻¹
c = 5.8455 (3) Å	T = 110 K
β = 90.771 (5)°	Needle, colorless
V = 1293.53 (12) Å³	0.54 × 0.13 × 0.08 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector	2537 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2223 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 10.5081 pixels mm^-1	θ_max = 74.0°, θ_min = 4.2°
ω scans	h = −19→17
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −16→17
T_min = 0.483, T_max = 0.558	l = −5→7
5083 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0574P)² + 0.4041P] where P = (F_o² + 2F_c²)/3
2537 reflections	(Δ/σ)_max = 0.001
173 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₆H₁₃ClO₂	V = 1293.53 (12) Å³
M_r = 272.71	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 15.6695 (7) Å	µ = 2.57 mm⁻¹
b = 14.1235 (8) Å	T = 110 K
c = 5.8455 (3) Å	0.54 × 0.13 × 0.08 mm
β = 90.771 (5)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector	2537 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2223 reflections with I > 2σ(I)
T_min = 0.483, T_max = 0.558	R_int = 0.021
5083 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.04	Δρ_max = 0.25 e Å⁻³
2537 reflections	Δρ_min = −0.22 e Å⁻³
173 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.

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	0.84683 (2)	0.61936 (3)	0.17788 (6)	0.02523 (13)
O1	0.47093 (7)	0.63259 (9)	0.70069 (19)	0.0289 (3)
O2	0.01821 (7)	0.61488 (8)	−0.07719 (19)	0.0241 (3)
C1	0.57310 (9)	0.62821 (10)	0.4074 (3)	0.0181 (3)
C2	0.63878 (9)	0.66090 (10)	0.5520 (2)	0.0188 (3)
H2	0.6255	0.6849	0.6990	0.023*
C3	0.72286 (9)	0.65859 (10)	0.4828 (3)	0.0198 (3)
H3	0.7672	0.6817	0.5800	0.024*
C4	0.74128 (9)	0.62174 (10)	0.2682 (3)	0.0193 (3)
C5	0.67775 (10)	0.58747 (11)	0.1233 (3)	0.0205 (3)
H5	0.6916	0.5612	−0.0212	0.025*
C6	0.59317 (9)	0.59211 (11)	0.1929 (3)	0.0202 (3)
H6	0.5489	0.5705	0.0934	0.024*
C7	0.48352 (9)	0.63066 (10)	0.4945 (3)	0.0200 (3)
C8	0.41225 (9)	0.63059 (11)	0.3255 (3)	0.0211 (3)
H8	0.4223	0.6467	0.1704	0.025*
C9	0.33359 (9)	0.60773 (11)	0.3930 (3)	0.0200 (3)
H9	0.3284	0.5885	0.5479	0.024*
C10	0.25468 (9)	0.60893 (10)	0.2562 (3)	0.0181 (3)
C11	0.24715 (9)	0.65496 (11)	0.0440 (3)	0.0202 (3)
H11	0.2960	0.6839	−0.0206	0.024*
C12	0.16938 (9)	0.65893 (11)	−0.0730 (3)	0.0200 (3)
H12	0.1648	0.6915	−0.2149	0.024*
C13	0.09809 (9)	0.61476 (10)	0.0193 (3)	0.0187 (3)
C14	0.10492 (9)	0.56679 (11)	0.2274 (3)	0.0202 (3)
H14	0.0567	0.5354	0.2882	0.024*
C15	0.18181 (9)	0.56513 (11)	0.3443 (2)	0.0199 (3)
H15	0.1856	0.5336	0.4877	0.024*
C16	0.00342 (10)	0.67344 (13)	−0.2722 (3)	0.0263 (3)
H16A	0.0140	0.7397	−0.2311	0.039*
H16B	−0.0559	0.6662	−0.3248	0.039*
H16C	0.0420	0.6547	−0.3948	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0180 (2)	0.0276 (2)	0.0302 (2)	0.00214 (13)	0.00556 (14)	0.00128 (15)
O1	0.0214 (6)	0.0441 (7)	0.0212 (6)	−0.0035 (5)	0.0006 (4)	0.0008 (5)
O2	0.0158 (5)	0.0266 (6)	0.0298 (6)	−0.0025 (4)	−0.0041 (4)	0.0048 (5)
C1	0.0174 (7)	0.0170 (7)	0.0198 (7)	−0.0009 (5)	−0.0019 (5)	0.0039 (6)
C2	0.0197 (7)	0.0188 (7)	0.0180 (7)	0.0019 (5)	−0.0009 (5)	−0.0002 (6)
C3	0.0185 (7)	0.0188 (7)	0.0221 (7)	0.0000 (5)	−0.0031 (5)	−0.0009 (6)
C4	0.0167 (7)	0.0172 (7)	0.0239 (7)	0.0018 (5)	0.0022 (6)	0.0034 (6)
C5	0.0251 (7)	0.0189 (7)	0.0176 (7)	0.0019 (6)	0.0016 (6)	−0.0002 (5)
C6	0.0194 (7)	0.0206 (7)	0.0206 (7)	−0.0015 (5)	−0.0038 (5)	0.0008 (6)
C7	0.0196 (7)	0.0193 (7)	0.0212 (7)	−0.0006 (5)	−0.0008 (6)	0.0012 (6)
C8	0.0178 (7)	0.0248 (8)	0.0207 (7)	0.0005 (6)	0.0000 (6)	0.0021 (6)
C9	0.0206 (7)	0.0189 (7)	0.0204 (7)	0.0017 (5)	−0.0001 (6)	0.0010 (6)
C10	0.0167 (7)	0.0170 (7)	0.0207 (7)	0.0023 (5)	0.0015 (5)	−0.0012 (6)
C11	0.0164 (7)	0.0222 (7)	0.0220 (7)	−0.0007 (5)	0.0032 (5)	0.0011 (6)
C12	0.0195 (7)	0.0215 (8)	0.0190 (7)	0.0001 (6)	0.0012 (5)	0.0008 (6)
C13	0.0161 (7)	0.0171 (7)	0.0228 (7)	0.0009 (5)	−0.0013 (5)	−0.0033 (6)
C14	0.0177 (7)	0.0187 (7)	0.0245 (7)	−0.0015 (5)	0.0039 (5)	0.0012 (6)
C15	0.0212 (7)	0.0186 (7)	0.0201 (7)	0.0016 (6)	0.0030 (5)	0.0015 (6)
C16	0.0213 (7)	0.0341 (9)	0.0235 (8)	0.0027 (6)	−0.0036 (6)	0.0014 (7)

Geometric parameters (Å, º) top

Cl1—C4	1.7431 (15)	C8—H8	0.9500
O1—C7	1.2240 (19)	C9—C10	1.464 (2)
O2—C13	1.3659 (18)	C9—H9	0.9500
O2—C16	1.4248 (19)	C10—C15	1.403 (2)
C1—C6	1.394 (2)	C10—C11	1.404 (2)
C1—C2	1.401 (2)	C11—C12	1.391 (2)
C1—C7	1.500 (2)	C11—H11	0.9500
C2—C3	1.384 (2)	C12—C13	1.395 (2)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.392 (2)	C13—C14	1.395 (2)
C3—H3	0.9500	C14—C15	1.377 (2)
C4—C5	1.386 (2)	C14—H14	0.9500
C5—C6	1.393 (2)	C15—H15	0.9500
C5—H5	0.9500	C16—H16A	0.9800
C6—H6	0.9500	C16—H16B	0.9800
C7—C8	1.481 (2)	C16—H16C	0.9800
C8—C9	1.339 (2)

C13—O2—C16	118.00 (12)	C8—C9—H9	116.2
C6—C1—C2	119.36 (14)	C10—C9—H9	116.2
C6—C1—C7	122.52 (13)	C15—C10—C11	118.00 (13)
C2—C1—C7	118.09 (13)	C15—C10—C9	118.70 (14)
C3—C2—C1	120.69 (14)	C11—C10—C9	123.25 (13)
C3—C2—H2	119.7	C12—C11—C10	121.06 (13)
C1—C2—H2	119.7	C12—C11—H11	119.5
C2—C3—C4	118.82 (13)	C10—C11—H11	119.5
C2—C3—H3	120.6	C11—C12—C13	119.52 (14)
C4—C3—H3	120.6	C11—C12—H12	120.2
C5—C4—C3	121.70 (14)	C13—C12—H12	120.2
C5—C4—Cl1	119.01 (12)	O2—C13—C12	125.02 (13)
C3—C4—Cl1	119.29 (11)	O2—C13—C14	114.83 (13)
C4—C5—C6	118.91 (14)	C12—C13—C14	120.15 (13)
C4—C5—H5	120.5	C15—C14—C13	119.82 (14)
C6—C5—H5	120.5	C15—C14—H14	120.1
C5—C6—C1	120.48 (13)	C13—C14—H14	120.1
C5—C6—H6	119.8	C14—C15—C10	121.41 (14)
C1—C6—H6	119.8	C14—C15—H15	119.3
O1—C7—C8	121.77 (14)	C10—C15—H15	119.3
O1—C7—C1	119.92 (13)	O2—C16—H16A	109.5
C8—C7—C1	118.31 (13)	O2—C16—H16B	109.5
C9—C8—C7	119.51 (14)	H16A—C16—H16B	109.5
C9—C8—H8	120.2	O2—C16—H16C	109.5
C7—C8—H8	120.2	H16A—C16—H16C	109.5
C8—C9—C10	127.64 (14)	H16B—C16—H16C	109.5

C6—C1—C2—C3	0.7 (2)	C7—C8—C9—C10	176.11 (14)
C7—C1—C2—C3	178.69 (13)	C8—C9—C10—C15	167.66 (15)
C1—C2—C3—C4	−1.0 (2)	C8—C9—C10—C11	−14.8 (2)
C2—C3—C4—C5	−0.1 (2)	C15—C10—C11—C12	1.4 (2)
C2—C3—C4—Cl1	179.45 (11)	C9—C10—C11—C12	−176.08 (14)
C3—C4—C5—C6	1.4 (2)	C10—C11—C12—C13	−1.4 (2)
Cl1—C4—C5—C6	−178.06 (11)	C16—O2—C13—C12	−7.9 (2)
C4—C5—C6—C1	−1.8 (2)	C16—O2—C13—C14	171.26 (13)
C2—C1—C6—C5	0.7 (2)	C11—C12—C13—O2	178.95 (14)
C7—C1—C6—C5	−177.17 (14)	C11—C12—C13—C14	−0.2 (2)
C6—C1—C7—O1	155.92 (15)	O2—C13—C14—C15	−177.58 (13)
C2—C1—C7—O1	−22.0 (2)	C12—C13—C14—C15	1.6 (2)
C6—C1—C7—C8	−24.0 (2)	C13—C14—C15—C10	−1.6 (2)
C2—C1—C7—C8	158.05 (14)	C11—C10—C15—C14	0.0 (2)
O1—C7—C8—C9	−17.5 (2)	C9—C10—C15—C14	177.68 (13)
C1—C7—C8—C9	162.41 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1	0.95	2.47	2.8080 (19)	101
C2—H2···Cg1ⁱ	0.95	2.85	3.4675 (15)	124
C12—H12···Cg2ⁱⁱ	0.95	2.92	3.6616 (17)	136

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃ClO₂
M_r	272.71
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	110
a, b, c (Å)	15.6695 (7), 14.1235 (8), 5.8455 (3)
β (°)	90.771 (5)
V (Å³)	1293.53 (12)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.57
Crystal size (mm)	0.54 × 0.13 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.483, 0.558
No. of measured, independent and observed [I > 2σ(I)] reflections	5083, 2537, 2223
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.096, 1.04
No. of reflections	2537
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.22

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1	0.95	2.47	2.8080 (19)	100.6
C2—H2···Cg1ⁱ	0.95	2.85	3.4675 (15)	124
C12—H12···Cg2ⁱⁱ	0.95	2.92	3.6616 (17)	136

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+3/2, z−1/2.

Acknowledgements

SS thanks Mangalore University and the UGC SAP for financial assistance for the purchase of chemicals. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125–1149. Web of Science PubMed CAS Google Scholar
Harrison, W. T. A., Yathirajan, H. S., Sarojini, B. K., Narayana, B. & Indira, J. (2006). Acta Cryst. E62, o1647–o1649. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jasinski, J. P., Butcher, R. J., Mayekar, A. N., Yathirajan, H. S. & Narayana, B. (2009). J. Chem. Crystallogr. 39, 157–162. Web of Science CSD CrossRef CAS Google Scholar
Lin, Y. M., Zhou, Y., Flavin, M. T., Zhou, L. M., Nie, W. & Chen, F. C. (2002). Bioorg. Med. Chem. 10, 2795–2802. Web of Science CrossRef PubMed CAS Google Scholar
Nakamura, C., Kawasaki, N., Miyataka, H., Jayachandran, E., Kim, I., Kirk, K. L., Taguchi, T., Takeuchi, Y., Hori, H. & Satoh, T. (2002). Bioorg. Med. Chem. 10, 699–706. Web of Science CrossRef PubMed CAS Google Scholar
Nowakowska, Z. (2007). Eur. J. Med. Chem. 42, 125–137. Web of Science CrossRef PubMed CAS Google Scholar
Opletalova, V. & Sedivy, D. (1999). Ceska Slov. Farm. 48, 252–255. PubMed CAS Google Scholar
Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Poornesh, P., Shettigar, S., Umesh, G., Manjunatha, K. B., Prakash Kamath, K., Sarojini, B. K. & Narayana, B. (2009). Opt. Mater. 31, 854–859. Web of Science CrossRef CAS Google Scholar
Sarojini, B. K., Narayana, B., Ashalatha, B. V., Indira, J. & Lobo, K. J. (2006). J. Cryst. Growth, 295, 54–59. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shettigar, S., Chandrasekharan, K., Umesh, G., Sarojini, B. K. & Narayana, B. (2006). Polymer, 47, 3565–3567. Web of Science CrossRef CAS Google Scholar
Shettigar, S., Umesh, G., Chandrasekharan, K., Sarojini, B. K. & Narayana, B. (2008). Opt. Mater. 30, 1297–1303. Web of Science CrossRef CAS Google Scholar

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Volume 66| Part 2| February 2010| Pages o269-o270

https://doi.org/10.1107/S1600536809054956

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

A monoclinic polymorph of 1-(4-chloro­phen­yl)-3-(4-meth­oxy­phen­yl)prop-2-en-1-one

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Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

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A monoclinic polymorph of 1-(4-chlorophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one