2-(4-Chloro­phen­yl)-6-meth­oxy­chroman-4-one

Jasinski, J.P.; Pek, A.E.; Narayana, B.; Yathirajan, H.S.; Nayak, P.S.

doi:10.1107/S1600536810035816

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages o2546-o2547

doi:10.1107/S1600536810035816

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2-(4-Chlorophenyl)-6-methoxychroman-4-one

Jerry P. Jasinski,^a ^* Albert E. Pek,^a B. Narayana,^b H. S. Yathirajan ^c and Prakash S. Nayak ^b

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

(Received 17 August 2010; accepted 6 September 2010; online 11 September 2010)

In the title molecule, C₁₆H₁₃Cl O₃, the two aromatic rings form a dihedral angle of 65.3 (1)°. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers, which are further packed into columns propagating in [100] by weak C—H⋯π interactions.

Related literature

For the pharmacological and alkylating properties of chromenes (benzopyrans) and their derivatives and for their use as synthons for the synthesis of natural products, see: Brooks (1998 ); Chenera et al. (1993 ); Ellis et al. (1997 ); Gabor et al. (1988 ); Hatakeyama et al. (1988 ); Hyana & Saimoto, et al. (1987 ); Kooijman et al. (1984 ); Liu et al. (2007 ); Tang et al. (2007 ); Valenti et al. (1993 ). For related structures, see: Brito et al. (2008 ); Butcher et al. (2007 ); Li et al. (2007 ); Nallasivam et al. (2009 ); Hao et al. (2010 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₃ClO₃
M_r = 288.71
Triclinic, $[P \overline 1]$
a = 5.0188 (3) Å
b = 12.0138 (7) Å
c = 12.3708 (7) Å
α = 108.035 (5)°
β = 98.379 (4)°
γ = 91.820 (5)°
V = 699.33 (7) Å³
Z = 2
Cu Kα radiation
μ = 2.46 mm⁻¹
T = 293 K
0.40 × 0.35 × 0.20 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 = 0.590, T_max = 1.000
4431 measured reflections
2733 independent reflections
2318 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.156
S = 1.62
2733 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O2ⁱ	0.98	2.50	3.260 (2)	135
C8—H8B⋯Cg1ⁱⁱ	0.97	2.69	3.5709 (18)	151
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x+1, y, z.

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: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035816/cv2754sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035816/cv2754Isup2.hkl

checkCIF report

Comment top

Chromenes (benzopyrans) and their derivatives exhibit a wide spectrum of biological and pharmacological properties including spasmolytic, antisterility, anti-arrhytmic, cardionthonic, antiviral, anticancer and alkylating properties (Gabor et al., 1988; Brooks, 1998; Valenti et al., 1993; Hyana & Saimoto, et al. 1987; Tang et al., 2007). In addition, polyfunctionalized chromene units are present in numerous natural products (Hatakeyama et al., 1988). Chromanone derivatives are important synthons for the synthesis of natural products such as brazillin, hematoxylin, ripariochromene and clausenin (Kooijman et al., 1984; Ellis et al., 1997; Chenera et al., 1993; Liu et al., 2007). The crystal structures of some rleated chromene derivatives viz., 7-hydroxy-4-methyl-2H-chromen-2-one monohydrate (Butcher et al., 2007), 5,7-dimethoxy-3-(4-methoxyphenyl)-4H-chromen-4-one (Li et al., 2007), 5,7-dimethoxy-2-phenyl-4H-chromen-4-one (Nallasivam et al., 2009), 5-hydroxy-7-methoxy-4H-chromen-4-one (Brito et al., 2008) and 3-methyl-4H-chromen-4-one (Hao et al., 2010) have been reported. In view of the importance of chromene derivatives, the crystal structure of the title compound, (I), is reported.

In (I), 4-chloro phenyl ring is found bonded to a 6-methoxy-2,3-dihydro-4H-chromen-4-one ring at C7 which is in an S configuration (Fig.1). The fused pyran ring in the benzopyran moiety adopts a slightly distorted envelope conformation with puckering parameters Q, θ and ϕ of 0.4973 (16)A%, 122.19 (19)°, and 243.0 (2)°, respectively. The dihedral angles between the mean planes of the benzene and benzopyran rings is 65.3 (1)°. Bond distances (Allen et al., 1987) and angles are in normal ranges. Weak C—H···O hydrogen bond and C—H···π intermolecular interactions (where Cg1 is the centroid of ring C7—C12) are observed which contribute to crystal packing (Table 1).

Related literature top

For the pharmacological and alkylating properties of chromenes (benzopyrans) and their derivatives and for their use as synthons for the synthesis of natural products, see: Brooks (1998); Chenera et al. (1993); Ellis et al. (1997); Gabor et al. (1988); Hatakeyama et al. (1988); Hyana & Saimoto, et al. (1987); Kooijman et al. (1984); Liu et al. (2007); Tang et al. (2007); Valenti et al. (1993). For related structures, see: Brito et al. (2008); Butcher et al. (2007); Li et al. (2007); Nallasivam et al. (2009); Hao et al. (2010). For bond-length data, see: Allen et al. (1987).

Experimental top

To a mixture of 1-(2-hydroxy-5-methoxyphenyl)ethanone (1.66 g, 0.01 mol) and p-chloro benzaldehyde (1.4 g, 0.01 mol) in 30 ml e thanol, 10 ml of 10% potassium hydroxide solution was added and stirred at 5–10 C° for 24 h (Fig. 2). The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from DMF by the slow evaporation method and the yield of the compound was 75%. (m.p. 378 K).

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: PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of (I) showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Reaction scheme for (I).

2-(4-Chlorophenyl)-6-methoxychroman-4-one top

Crystal data top

C₁₆H₁₃ClO₃	Z = 2
M_r = 288.71	F(000) = 300
Triclinic, P1	D_x = 1.371 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 5.0188 (3) Å	Cell parameters from 2808 reflections
b = 12.0138 (7) Å	θ = 4.5–74.2°
c = 12.3708 (7) Å	µ = 2.46 mm⁻¹
α = 108.035 (5)°	T = 293 K
β = 98.379 (4)°	Block, colourless
γ = 91.820 (5)°	0.40 × 0.35 × 0.20 mm
V = 699.33 (7) Å³

Data collection top

Oxford Diffraction Xcalibur with a Ruby (Gemini Cu) detector diffractometer	2733 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2318 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Detector resolution: 10.5081 pixels mm^-1	θ_max = 74.3°, θ_min = 4.5°
ω scans	h = −6→5
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −14→14
T_min = 0.590, T_max = 1.000	l = −13→15
4431 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) = 0.156	H-atom parameters constrained
S = 1.62	w = 1/[σ²(F_o²) + (0.072P)²] where P = (F_o² + 2F_c²)/3
2733 reflections	(Δ/σ)_max < 0.001
183 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₆H₁₃ClO₃	γ = 91.820 (5)°
M_r = 288.71	V = 699.33 (7) Å³
Triclinic, P1	Z = 2
a = 5.0188 (3) Å	Cu Kα radiation
b = 12.0138 (7) Å	µ = 2.46 mm⁻¹
c = 12.3708 (7) Å	T = 293 K
α = 108.035 (5)°	0.40 × 0.35 × 0.20 mm
β = 98.379 (4)°

Data collection top

Oxford Diffraction Xcalibur with a Ruby (Gemini Cu) detector diffractometer	2733 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2318 reflections with I > 2σ(I)
T_min = 0.590, T_max = 1.000	R_int = 0.018
4431 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.62	Δρ_max = 0.17 e Å⁻³
2733 reflections	Δρ_min = −0.39 e Å⁻³
183 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	1.44159 (18)	1.09772 (6)	1.41015 (7)	0.1128 (4)
C15	0.1890 (4)	0.52826 (16)	0.74092 (15)	0.0510 (4)
H14	0.1871	0.4469	0.7205	0.061*
C10	0.3876 (3)	0.59907 (15)	0.82937 (14)	0.0445 (4)
C11	0.3896 (3)	0.72078 (15)	0.85979 (14)	0.0457 (4)
C5	0.8624 (4)	0.83325 (15)	1.12894 (15)	0.0486 (4)
C4	1.0438 (4)	0.90581 (17)	1.10279 (18)	0.0588 (5)
H4	1.0451	0.9004	1.0262	0.071*
C3	1.2237 (5)	0.98652 (19)	1.1888 (2)	0.0698 (6)
H3	1.3442	1.0356	1.1706	0.084*
C2	1.2221 (5)	0.99320 (18)	1.3011 (2)	0.0703 (6)
C6	0.8664 (5)	0.8411 (2)	1.24293 (19)	0.0714 (6)
H6	0.7459	0.7924	1.2617	0.098 (9)*
C1	1.0475 (6)	0.9205 (2)	1.3295 (2)	0.0830 (7)
H1	1.0510	0.9247	1.4061	0.100*
C12	0.1994 (4)	0.77156 (17)	0.79994 (16)	0.0547 (4)
H11	0.2034	0.8528	0.8183	0.066*
C14	−0.0029 (4)	0.57890 (18)	0.68435 (16)	0.0564 (5)
C13	0.0067 (4)	0.70101 (19)	0.71392 (17)	0.0610 (5)
H12	−0.1204	0.7352	0.6744	0.073*
C7	0.6684 (3)	0.74364 (14)	1.03660 (15)	0.0454 (4)
H7	0.5149	0.7247	1.0703	0.055*
C9	0.5995 (3)	0.54557 (14)	0.88808 (15)	0.0453 (4)
C8	0.7957 (3)	0.63138 (15)	0.98271 (15)	0.0483 (4)
H8B	0.8568	0.5958	1.0415	0.058*
H8A	0.9521	0.6497	0.9517	0.058*
O1	0.5707 (2)	0.79532 (10)	0.94837 (11)	0.0500 (3)
O2	0.6175 (3)	0.43987 (11)	0.86011 (12)	0.0597 (4)
O3	−0.2094 (3)	0.51981 (15)	0.59887 (13)	0.0759 (5)
C16	−0.2392 (5)	0.3957 (2)	0.5693 (2)	0.0841 (7)
H15A	−0.0793	0.3635	0.5425	0.126*
H15B	−0.3924	0.3652	0.5094	0.126*
H15C	−0.2661	0.3745	0.6358	0.126*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1341 (7)	0.0652 (4)	0.1049 (5)	−0.0140 (4)	−0.0625 (5)	0.0169 (3)
C15	0.0503 (10)	0.0501 (9)	0.0500 (9)	0.0020 (7)	0.0083 (8)	0.0124 (8)
C10	0.0406 (8)	0.0485 (9)	0.0462 (9)	0.0040 (7)	0.0085 (7)	0.0170 (7)
C11	0.0419 (8)	0.0491 (9)	0.0480 (9)	0.0028 (7)	0.0056 (7)	0.0192 (7)
C5	0.0470 (9)	0.0455 (9)	0.0520 (9)	0.0090 (7)	0.0023 (7)	0.0157 (7)
C4	0.0606 (11)	0.0546 (11)	0.0586 (11)	−0.0020 (9)	0.0036 (9)	0.0181 (9)
C3	0.0647 (13)	0.0559 (11)	0.0834 (15)	−0.0077 (9)	−0.0067 (11)	0.0239 (10)
C2	0.0761 (14)	0.0470 (10)	0.0716 (13)	0.0032 (9)	−0.0259 (11)	0.0129 (9)
C6	0.0796 (15)	0.0738 (14)	0.0572 (12)	−0.0087 (11)	0.0004 (10)	0.0222 (10)
C1	0.1029 (19)	0.0826 (16)	0.0531 (12)	−0.0017 (14)	−0.0109 (12)	0.0182 (11)
C12	0.0571 (11)	0.0532 (10)	0.0569 (10)	0.0092 (8)	0.0031 (8)	0.0242 (8)
C14	0.0500 (10)	0.0679 (12)	0.0459 (9)	0.0011 (8)	0.0007 (7)	0.0139 (8)
C13	0.0573 (11)	0.0707 (12)	0.0551 (10)	0.0127 (9)	−0.0032 (9)	0.0251 (9)
C7	0.0432 (9)	0.0458 (9)	0.0496 (9)	0.0051 (7)	0.0050 (7)	0.0194 (7)
C9	0.0425 (9)	0.0446 (9)	0.0515 (9)	0.0056 (7)	0.0108 (7)	0.0175 (7)
C8	0.0414 (9)	0.0490 (9)	0.0555 (10)	0.0071 (7)	0.0040 (7)	0.0195 (8)
O1	0.0508 (7)	0.0434 (6)	0.0553 (7)	0.0009 (5)	−0.0033 (5)	0.0206 (5)
O2	0.0647 (8)	0.0437 (7)	0.0688 (8)	0.0083 (6)	0.0041 (6)	0.0182 (6)
O3	0.0662 (9)	0.0812 (11)	0.0629 (9)	−0.0018 (7)	−0.0170 (7)	0.0113 (8)
C16	0.0807 (16)	0.0814 (16)	0.0677 (14)	−0.0132 (13)	−0.0115 (12)	0.0041 (12)

Geometric parameters (Å, º) top

Cl1—C2	1.744 (2)	C1—H1	0.9300
C15—C14	1.376 (3)	C12—C13	1.370 (3)
C15—C10	1.402 (2)	C12—H11	0.9300
C15—H14	0.9300	C14—O3	1.366 (2)
C10—C11	1.392 (2)	C14—C13	1.395 (3)
C10—C9	1.476 (2)	C13—H12	0.9300
C11—O1	1.371 (2)	C7—O1	1.449 (2)
C11—C12	1.393 (2)	C7—C8	1.515 (2)
C5—C6	1.381 (3)	C7—H7	0.9800
C5—C4	1.380 (3)	C9—O2	1.219 (2)
C5—C7	1.503 (2)	C9—C8	1.502 (2)
C4—C3	1.383 (3)	C8—H8B	0.9700
C4—H4	0.9300	C8—H8A	0.9700
C3—C2	1.367 (4)	O3—C16	1.418 (3)
C3—H3	0.9300	C16—H15A	0.9600
C2—C1	1.373 (4)	C16—H15B	0.9600
C6—C1	1.383 (3)	C16—H15C	0.9600
C6—H6	0.9300

C14—C15—C10	120.12 (17)	C15—C14—O3	125.69 (19)
C14—C15—H14	119.9	C15—C14—C13	119.31 (17)
C10—C15—H14	119.9	O3—C14—C13	115.00 (18)
C11—C10—C15	119.75 (16)	C12—C13—C14	121.37 (17)
C11—C10—C9	119.71 (15)	C12—C13—H12	119.3
C15—C10—C9	120.51 (15)	C14—C13—H12	119.3
O1—C11—C10	122.90 (15)	O1—C7—C5	108.13 (13)
O1—C11—C12	117.23 (15)	O1—C7—C8	109.43 (14)
C10—C11—C12	119.86 (16)	C5—C7—C8	112.84 (14)
C6—C5—C4	118.74 (19)	O1—C7—H7	108.8
C6—C5—C7	119.48 (18)	C5—C7—H7	108.8
C4—C5—C7	121.74 (16)	C8—C7—H7	108.8
C5—C4—C3	120.9 (2)	O2—C9—C10	122.50 (16)
C5—C4—H4	119.5	O2—C9—C8	122.51 (16)
C3—C4—H4	119.5	C10—C9—C8	114.97 (14)
C2—C3—C4	119.2 (2)	C7—C8—C9	111.46 (14)
C2—C3—H3	120.4	C7—C8—H8B	109.3
C4—C3—H3	120.4	C9—C8—H8B	109.3
C3—C2—C1	121.2 (2)	C7—C8—H8A	109.3
C3—C2—Cl1	119.3 (2)	C9—C8—H8A	109.3
C1—C2—Cl1	119.45 (19)	H8B—C8—H8A	108.0
C5—C6—C1	120.8 (2)	C11—O1—C7	112.96 (12)
C5—C6—H6	119.6	C14—O3—C16	117.73 (18)
C1—C6—H6	119.6	O3—C16—H15A	109.5
C2—C1—C6	119.1 (2)	O3—C16—H15B	109.5
C2—C1—H1	120.4	H15A—C16—H15B	109.5
C6—C1—H1	120.4	O3—C16—H15C	109.5
C13—C12—C11	119.55 (18)	H15A—C16—H15C	109.5
C13—C12—H11	120.2	H15B—C16—H15C	109.5
C11—C12—H11	120.2

C14—C15—C10—C11	0.1 (3)	C15—C14—C13—C12	−1.5 (3)
C14—C15—C10—C9	−178.06 (16)	O3—C14—C13—C12	178.56 (19)
C15—C10—C11—O1	177.30 (15)	C6—C5—C7—O1	142.77 (18)
C9—C10—C11—O1	−4.6 (2)	C4—C5—C7—O1	−39.4 (2)
C15—C10—C11—C12	−1.9 (3)	C6—C5—C7—C8	−96.0 (2)
C9—C10—C11—C12	176.21 (15)	C4—C5—C7—C8	81.8 (2)
C6—C5—C4—C3	−1.1 (3)	C11—C10—C9—O2	−175.33 (17)
C7—C5—C4—C3	−178.99 (18)	C15—C10—C9—O2	2.8 (3)
C5—C4—C3—C2	0.6 (3)	C11—C10—C9—C8	3.1 (2)
C4—C3—C2—C1	0.7 (4)	C15—C10—C9—C8	−178.80 (15)
C4—C3—C2—Cl1	−178.13 (16)	O1—C7—C8—C9	−57.54 (18)
C4—C5—C6—C1	0.4 (3)	C5—C7—C8—C9	−177.98 (14)
C7—C5—C6—C1	178.3 (2)	O2—C9—C8—C7	−154.04 (17)
C3—C2—C1—C6	−1.4 (4)	C10—C9—C8—C7	27.6 (2)
Cl1—C2—C1—C6	177.40 (19)	C10—C11—O1—C7	−26.7 (2)
C5—C6—C1—C2	0.9 (4)	C12—C11—O1—C7	152.50 (16)
O1—C11—C12—C13	−177.23 (17)	C5—C7—O1—C11	−179.56 (13)
C10—C11—C12—C13	2.0 (3)	C8—C7—O1—C11	57.17 (18)
C10—C15—C14—O3	−178.47 (18)	C15—C14—O3—C16	3.6 (3)
C10—C15—C14—C13	1.6 (3)	C13—C14—O3—C16	−176.6 (2)
C11—C12—C13—C14	−0.3 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2ⁱ	0.98	2.50	3.260 (2)	135
C8—H8B···Cg1ⁱⁱ	0.97	2.69	3.5709 (18)	151

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃ClO₃
M_r	288.71
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	5.0188 (3), 12.0138 (7), 12.3708 (7)
α, β, γ (°)	108.035 (5), 98.379 (4), 91.820 (5)
V (Å³)	699.33 (7)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	2.46
Crystal size (mm)	0.40 × 0.35 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur with a Ruby (Gemini Cu) detector diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.590, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4431, 2733, 2318
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.156, 1.62
No. of reflections	2733
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.39

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2ⁱ	0.98	2.50	3.260 (2)	134.7
C8—H8B···Cg1ⁱⁱ	0.97	2.69	3.5709 (18)	151

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

Acknowledgements

BN thanks the UGC for a SAP Chemical grant. HSY thanks UOM for sabbatical leave. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

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Volume 66| Part 10| October 2010| Pages o2546-o2547

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