rac-2-Iodo-3,4-dihydro­naphthalen-1(2H)-one

Raza, A.R.; Tahir, M.N.; Sultan, A.; Danish, M.; Sohail, M.

doi:10.1107/S1600536809049095

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3172

doi:10.1107/S1600536809049095

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rac-2-Iodo-3,4-dihydronaphthalen-1(2H)-one

Abdul Rauf Raza,^a M. Nawaz Tahir,^b ^* Ayesha Sultan,^a Muhammad Danish ^a and Muhammad Sohail ^a

^aDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 17 November 2009; accepted 18 November 2009; online 21 November 2009)

In the title compound, C₁₀H₉IO, the asymmetric unit contains two molecules, in which the iodo-bearing six-membered rings adopt envelope conformations [displacements of the flap atoms = 0.419 (3) and 0.431 (3) Å]. In both molecules, the I atoms are disordered over two set of sites in 0.54 (4):0.46 (4) and 0.71 (3):0.29 (3) ratios. In the crystal, the packing features a weak C—H⋯π interaction.

Related literature

For a related structure, see: Haddad (1986 ).

Experimental

Crystal data

C₁₀H₉IO
M_r = 272.07
Monoclinic, P 2₁ /c
a = 6.115 (5) Å
b = 19.658 (4) Å
c = 15.896 (5) Å
β = 90.551 (5)°
V = 1910.7 (17) Å³
Z = 8
Mo Kα radiation
μ = 3.31 mm⁻¹
T = 296 K
0.28 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.685, T_max = 0.717
19043 measured reflections
4397 independent reflections
3632 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.059
S = 1.07
4397 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cg3	0.93	2.95	3.700 (4)	139
Cg3 is the centroid of the C11–C16 ring.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049095/hb5236sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049095/hb5236Isup2.hkl

checkCIF report

Comment top

The title compound (I, Fig. 1) is an intermediate for the total synthesis of steroidal hormones. The ctystal structures of (II) 2,2-Dibromo-3,4-dihydro-1(2H)-naphthalenone (Haddad, 1986) has been published, which seems relavent to (I).

The asymmetric unit of title compound consists of two individual molecules which are clearly racemate. In the molecule having (S)-configuration, the I-atom containing ring A (C1/C6/C7—C10) is twisted with maximum puckering amplitude Q_T = 0.431 (3) Å, whereas in (R)-configuration the puckering parameter is Q_T = 0.419 (3) Å. In two molecules the groups of benzene rings along with two adjacent C-atoms, C (C1—C6/C7/C10) and D (C11—C16/C17/C20) are planar with maximum r. m. s. deviations of 0.0114 and 0.0280 Å respectively, from the respective mean square planes. The dihedral angle between C/D is 66.83 (7) Å. In the first molecule the I-atom is disordered over two set of sites having occupancy ratio of 0.54 (4):0.46 (4). Similarly in the other molecule the I-atom is disordered over two set of sites having occupancy ratio of 0.71 (3):0.29 (3). The molecules are stabilized due to C–H···π interactions (Table 1).

Related literature top

For a related structure, see: Haddad (1986). Cg3 is the centroid of the C11–C16 ring.

Experimental top

A solution of I₂ (7.75 g, 30.5 mmol) in CHCl₃ was added as drops to a solution of 1-tetralone (2.198 g, 15.2 mmol) in acetic acid (9.156 g, 0.1526 mol) and refluxed for 28 h. The H₂O (30 ml) was added for partitioning. The reaction mixture was extracted with CHCl₃ (3 × 15 ml). The combined organic layer was concentrated in vacuo, the crude was dissolved in ethyl acetate, washed with 5% Na₂S₂O₃ (2 × 15 ml), dried over anhydrous Na₂SO₄, filtered, boiled with charcoal, concentrated under reduce pressure and allowed for crystallization, which afforded colourless prisms (89%) of (I).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of (I) with the I atoms having greater occupancies. The displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. View of (I) with the I atoms having lesser occupancies. The displacement ellipsoids are drawn at the 30% probability level.

rac-2-Iodo-3,4-dihydronaphthalen-1(2H)-one top

Crystal data top

C₁₀H₉IO	F(000) = 1040
M_r = 272.07	D_x = 1.892 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4397 reflections
a = 6.115 (5) Å	θ = 2.4–27.8°
b = 19.658 (4) Å	µ = 3.31 mm⁻¹
c = 15.896 (5) Å	T = 296 K
β = 90.551 (5)°	Prism, colourless
V = 1910.7 (17) Å³	0.28 × 0.20 × 0.18 mm
Z = 8

Data collection top

Bruker Kappa APEXII CCD diffractometer	4397 independent reflections
Radiation source: fine-focus sealed tube	3632 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 7.50 pixels mm^-1	θ_max = 27.8°, θ_min = 2.4°
ω scans	h = −8→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −25→24
T_min = 0.685, T_max = 0.717	l = −20→20
19043 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)] = 0.024	H-atom parameters constrained
wR(F²) = 0.059	w = 1/[σ²(F_o²) + (0.0273P)² + 0.6672P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.002
4397 reflections	Δρ_max = 0.39 e Å⁻³
238 parameters	Δρ_min = −0.50 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00283 (17)

Crystal data top

C₁₀H₉IO	V = 1910.7 (17) Å³
M_r = 272.07	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.115 (5) Å	µ = 3.31 mm⁻¹
b = 19.658 (4) Å	T = 296 K
c = 15.896 (5) Å	0.28 × 0.20 × 0.18 mm
β = 90.551 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4397 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3632 reflections with I > 2σ(I)
T_min = 0.685, T_max = 0.717	R_int = 0.026
19043 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.059	H-atom parameters constrained
S = 1.07	Δρ_max = 0.39 e Å⁻³
4397 reflections	Δρ_min = −0.50 e Å⁻³
238 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	Occ. (<1)
I1A	0.8199 (5)	0.0828 (2)	0.36895 (19)	0.0502 (6)	0.54 (4)
I1B	0.8299 (7)	0.0783 (3)	0.3658 (2)	0.0622 (8)	0.46 (4)
O1	0.6627 (3)	0.25061 (10)	0.31382 (12)	0.0512 (6)
C1	0.9910 (4)	0.17057 (12)	0.15222 (17)	0.0408 (8)
C2	0.9965 (5)	0.16572 (14)	0.06450 (19)	0.0573 (10)
C3	0.8386 (6)	0.19473 (15)	0.01454 (19)	0.0637 (10)
C4	0.6694 (6)	0.23029 (15)	0.05043 (19)	0.0621 (11)
C5	0.6596 (4)	0.23677 (13)	0.13679 (17)	0.0473 (9)
C6	0.8181 (3)	0.20662 (11)	0.18883 (15)	0.0350 (7)
C7	0.8027 (3)	0.21515 (11)	0.28175 (15)	0.0356 (7)
C8	0.9707 (4)	0.17888 (13)	0.33563 (17)	0.0439 (8)
C9	1.1881 (4)	0.16933 (15)	0.2919 (2)	0.0546 (9)
C10	1.1619 (4)	0.13632 (14)	0.20632 (19)	0.0518 (9)
I2A	0.2833 (4)	0.51127 (14)	0.4019 (2)	0.0524 (4)	0.71 (3)
I2B	0.2948 (9)	0.5150 (3)	0.3949 (5)	0.0551 (13)	0.29 (3)
O2	0.1573 (3)	0.33920 (10)	0.34826 (14)	0.0590 (7)
C11	0.4861 (4)	0.42382 (11)	0.19085 (17)	0.0395 (8)
C12	0.4975 (5)	0.42831 (14)	0.1038 (2)	0.0593 (11)
C13	0.3390 (7)	0.39932 (18)	0.0525 (2)	0.0735 (13)
C14	0.1666 (6)	0.36502 (18)	0.0870 (2)	0.0725 (12)
C15	0.1531 (4)	0.35857 (13)	0.1724 (2)	0.0528 (10)
C16	0.3121 (3)	0.38740 (11)	0.22589 (16)	0.0366 (7)
C17	0.2928 (4)	0.37754 (11)	0.31794 (16)	0.0385 (7)
C18	0.4509 (4)	0.41620 (12)	0.37374 (17)	0.0431 (8)
C19	0.6704 (4)	0.42740 (14)	0.33282 (19)	0.0504 (9)
C20	0.6513 (4)	0.45891 (14)	0.24640 (19)	0.0496 (9)
H2	1.11050	0.14215	0.03943	0.0687*
H3	0.84562	0.19042	−0.04364	0.0763*
H4	0.56189	0.24993	0.01653	0.0746*
H5	0.54622	0.26144	0.16068	0.0568*
H8	0.99519	0.20536	0.38710	0.0527*
H9A	1.25810	0.21327	0.28537	0.0654*
H9B	1.28268	0.14126	0.32686	0.0654*
H10A	1.30098	0.13765	0.17757	0.0620*
H10B	1.12210	0.08895	0.21380	0.0620*
H12	0.61398	0.45126	0.07953	0.0712*
H13	0.34957	0.40313	−0.00567	0.0882*
H14	0.05908	0.34619	0.05236	0.0868*
H15	0.03679	0.33471	0.19547	0.0632*
H18	0.47290	0.39074	0.42614	0.0517*
H19A	0.75860	0.45680	0.36852	0.0605*
H19B	0.74537	0.38409	0.32833	0.0605*
H20A	0.61044	0.50634	0.25223	0.0596*
H20B	0.79302	0.45732	0.21957	0.0596*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1A	0.0533 (13)	0.0521 (9)	0.0453 (9)	−0.0069 (5)	0.0019 (5)	0.0139 (8)
I1B	0.084 (2)	0.0428 (9)	0.0599 (13)	−0.0067 (6)	0.0130 (10)	−0.0018 (11)
O1	0.0456 (10)	0.0531 (11)	0.0550 (12)	0.0073 (8)	0.0063 (8)	−0.0161 (9)
C1	0.0450 (12)	0.0273 (12)	0.0504 (16)	−0.0049 (9)	0.0138 (11)	0.0004 (11)
C2	0.0773 (19)	0.0391 (15)	0.0561 (19)	−0.0096 (13)	0.0319 (16)	−0.0049 (13)
C3	0.102 (2)	0.0490 (17)	0.0402 (16)	−0.0163 (17)	0.0091 (16)	0.0025 (14)
C4	0.083 (2)	0.0521 (18)	0.0510 (19)	−0.0057 (15)	−0.0130 (16)	0.0118 (14)
C5	0.0502 (14)	0.0387 (14)	0.0530 (17)	0.0023 (11)	−0.0036 (12)	0.0000 (12)
C6	0.0370 (11)	0.0243 (11)	0.0439 (14)	−0.0035 (9)	0.0054 (10)	−0.0011 (10)
C7	0.0322 (11)	0.0297 (12)	0.0448 (14)	−0.0045 (9)	0.0018 (10)	−0.0046 (10)
C8	0.0442 (13)	0.0389 (14)	0.0485 (15)	−0.0046 (10)	−0.0082 (11)	−0.0064 (11)
C9	0.0346 (12)	0.0499 (16)	0.079 (2)	−0.0019 (11)	−0.0078 (12)	0.0078 (15)
C10	0.0379 (13)	0.0419 (15)	0.076 (2)	0.0064 (10)	0.0160 (13)	0.0039 (14)
I2A	0.0475 (8)	0.0585 (9)	0.0512 (5)	0.0129 (3)	−0.0063 (3)	−0.0177 (5)
I2B	0.077 (3)	0.0322 (19)	0.0562 (13)	0.0131 (8)	0.0055 (13)	−0.0043 (12)
O2	0.0550 (11)	0.0514 (12)	0.0709 (14)	−0.0111 (9)	0.0206 (10)	0.0053 (10)
C11	0.0416 (12)	0.0274 (12)	0.0496 (16)	0.0011 (9)	0.0093 (11)	−0.0039 (10)
C12	0.0745 (19)	0.0488 (17)	0.0551 (19)	−0.0020 (14)	0.0204 (15)	0.0010 (14)
C13	0.105 (3)	0.071 (2)	0.0446 (18)	0.006 (2)	0.0004 (18)	−0.0078 (16)
C14	0.086 (2)	0.064 (2)	0.067 (2)	−0.0004 (18)	−0.0220 (19)	−0.0170 (17)
C15	0.0511 (15)	0.0381 (14)	0.069 (2)	−0.0081 (11)	−0.0073 (13)	−0.0075 (13)
C16	0.0355 (11)	0.0259 (12)	0.0484 (15)	0.0012 (9)	0.0025 (10)	−0.0033 (10)
C17	0.0356 (11)	0.0283 (12)	0.0517 (15)	0.0032 (9)	0.0071 (10)	0.0012 (10)
C18	0.0445 (13)	0.0427 (14)	0.0420 (15)	0.0102 (10)	−0.0023 (11)	0.0008 (11)
C19	0.0341 (12)	0.0504 (16)	0.0665 (19)	0.0033 (10)	−0.0068 (12)	−0.0087 (13)
C20	0.0347 (12)	0.0433 (15)	0.071 (2)	−0.0092 (10)	0.0103 (12)	−0.0039 (13)

Geometric parameters (Å, º) top

I1A—C8	2.170 (5)	C9—H9B	0.9700
I1B—C8	2.211 (6)	C10—H10A	0.9700
I2A—C18	2.180 (4)	C10—H10B	0.9700
I2B—C18	2.192 (7)	C11—C12	1.389 (4)
O1—C7	1.220 (3)	C11—C16	1.402 (3)
O2—C17	1.223 (3)	C11—C20	1.503 (4)
C1—C6	1.404 (3)	C12—C13	1.384 (5)
C1—C2	1.398 (4)	C13—C14	1.370 (5)
C1—C10	1.506 (4)	C14—C15	1.367 (5)
C2—C3	1.369 (5)	C15—C16	1.405 (4)
C3—C4	1.377 (5)	C16—C17	1.482 (4)
C4—C5	1.381 (4)	C17—C18	1.511 (4)
C5—C6	1.400 (4)	C18—C19	1.513 (4)
C6—C7	1.490 (4)	C19—C20	1.510 (4)
C7—C8	1.510 (4)	C12—H12	0.9300
C8—C9	1.518 (4)	C13—H13	0.9300
C9—C10	1.514 (4)	C14—H14	0.9300
C2—H2	0.9300	C15—H15	0.9300
C3—H3	0.9300	C18—H18	0.9800
C4—H4	0.9300	C19—H19A	0.9700
C5—H5	0.9300	C19—H19B	0.9700
C8—H8	0.9800	C20—H20A	0.9700
C9—H9A	0.9700	C20—H20B	0.9700

C2—C1—C6	118.2 (2)	C12—C11—C16	118.3 (2)
C2—C1—C10	121.1 (2)	C12—C11—C20	121.1 (2)
C6—C1—C10	120.7 (2)	C16—C11—C20	120.6 (2)
C1—C2—C3	121.8 (3)	C11—C12—C13	121.3 (3)
C2—C3—C4	120.0 (3)	C12—C13—C14	120.3 (3)
C3—C4—C5	119.9 (3)	C13—C14—C15	119.8 (3)
C4—C5—C6	120.8 (2)	C14—C15—C16	121.0 (3)
C1—C6—C5	119.3 (2)	C11—C16—C15	119.3 (2)
C1—C6—C7	121.5 (2)	C11—C16—C17	121.8 (2)
C5—C6—C7	119.21 (19)	C15—C16—C17	118.9 (2)
O1—C7—C6	122.0 (2)	O2—C17—C16	122.1 (2)
O1—C7—C8	120.6 (2)	O2—C17—C18	120.7 (2)
C6—C7—C8	117.38 (18)	C16—C17—C18	117.2 (2)
I1A—C8—C7	105.13 (17)	I2A—C18—C17	104.62 (17)
I1A—C8—C9	112.4 (2)	I2A—C18—C19	112.60 (18)
I1B—C8—C7	106.32 (18)	I2B—C18—C17	105.0 (2)
I1B—C8—C9	109.5 (2)	I2B—C18—C19	109.1 (2)
C7—C8—C9	113.1 (2)	C17—C18—C19	112.7 (2)
C8—C9—C10	112.3 (2)	C18—C19—C20	112.9 (2)
C1—C10—C9	112.9 (2)	C11—C20—C19	113.1 (2)
C1—C2—H2	119.00	C11—C12—H12	119.00
C3—C2—H2	119.00	C13—C12—H12	119.00
C2—C3—H3	120.00	C12—C13—H13	120.00
C4—C3—H3	120.00	C14—C13—H13	120.00
C3—C4—H4	120.00	C13—C14—H14	120.00
C5—C4—H4	120.00	C15—C14—H14	120.00
C4—C5—H5	120.00	C14—C15—H15	119.00
C6—C5—H5	120.00	C16—C15—H15	119.00
I1A—C8—H8	109.00	I2A—C18—H18	109.00
I1B—C8—H8	111.00	I2B—C18—H18	112.00
C7—C8—H8	109.00	C17—C18—H18	109.00
C9—C8—H8	109.00	C19—C18—H18	109.00
C8—C9—H9A	109.00	C18—C19—H19A	109.00
C8—C9—H9B	109.00	C18—C19—H19B	109.00
C10—C9—H9A	109.00	C20—C19—H19A	109.00
C10—C9—H9B	109.00	C20—C19—H19B	109.00
H9A—C9—H9B	108.00	H19A—C19—H19B	108.00
C1—C10—H10A	109.00	C11—C20—H20A	109.00
C1—C10—H10B	109.00	C11—C20—H20B	109.00
C9—C10—H10A	109.00	C19—C20—H20A	109.00
C9—C10—H10B	109.00	C19—C20—H20B	109.00
H10A—C10—H10B	108.00	H20A—C20—H20B	108.00

C6—C1—C2—C3	−0.3 (4)	C16—C11—C12—C13	1.7 (4)
C10—C1—C2—C3	177.9 (3)	C20—C11—C12—C13	−176.3 (3)
C2—C1—C6—C5	−0.6 (3)	C12—C11—C16—C15	−1.8 (3)
C2—C1—C6—C7	−178.9 (2)	C12—C11—C16—C17	177.3 (2)
C10—C1—C6—C5	−178.8 (2)	C20—C11—C16—C15	176.2 (2)
C10—C1—C6—C7	2.9 (3)	C20—C11—C16—C17	−4.7 (3)
C2—C1—C10—C9	156.0 (2)	C12—C11—C20—C19	−157.1 (2)
C6—C1—C10—C9	−25.8 (3)	C16—C11—C20—C19	25.0 (3)
C1—C2—C3—C4	0.5 (5)	C11—C12—C13—C14	−0.3 (5)
C2—C3—C4—C5	0.2 (5)	C12—C13—C14—C15	−1.0 (5)
C3—C4—C5—C6	−1.1 (4)	C13—C14—C15—C16	0.9 (5)
C4—C5—C6—C1	1.3 (4)	C14—C15—C16—C11	0.6 (4)
C4—C5—C6—C7	179.6 (2)	C14—C15—C16—C17	−178.6 (3)
C1—C6—C7—O1	174.4 (2)	C11—C16—C17—O2	−171.0 (2)
C1—C6—C7—C8	−4.7 (3)	C11—C16—C17—C18	8.1 (3)
C5—C6—C7—O1	−4.0 (3)	C15—C16—C17—O2	8.1 (3)
C5—C6—C7—C8	177.1 (2)	C15—C16—C17—C18	−172.9 (2)
O1—C7—C8—I1A	87.3 (2)	O2—C17—C18—I2A	−89.8 (2)
O1—C7—C8—C9	−149.8 (2)	O2—C17—C18—C19	147.6 (2)
C6—C7—C8—I1A	−93.7 (2)	C16—C17—C18—I2A	91.2 (2)
C6—C7—C8—C9	29.3 (3)	C16—C17—C18—C19	−31.5 (3)
I1A—C8—C9—C10	66.6 (3)	I2A—C18—C19—C20	−65.9 (3)
C7—C8—C9—C10	−52.2 (3)	C17—C18—C19—C20	52.1 (3)
C8—C9—C10—C1	50.1 (3)	C18—C19—C20—C11	−48.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg3	0.93	2.95	3.700 (4)	139

Experimental details

Crystal data
Chemical formula	C₁₀H₉IO
M_r	272.07
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	6.115 (5), 19.658 (4), 15.896 (5)
β (°)	90.551 (5)
V (Å³)	1910.7 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.31
Crystal size (mm)	0.28 × 0.20 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.685, 0.717
No. of measured, independent and observed [I > 2σ(I)] reflections	19043, 4397, 3632
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.059, 1.07
No. of reflections	4397
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.50

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg3	0.93	2.95	3.700 (4)	139

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Haddad, S. F. (1986). Acta Cryst. C42, 581–584. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 12| December 2009| Page o3172

doi:10.1107/S1600536809049095

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