2-(1H-1,2,3-Benzotriazol-1-yl)-1-(4-ethyl­benzo­yl)ethyl 2,4-dichloro­benzoate

Zeng, W.-L.

doi:10.1107/S1600536808011951

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o942

doi:10.1107/S1600536808011951

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2-(1H-1,2,3-Benzotriazol-1-yl)-1-(4-ethylbenzoyl)ethyl 2,4-dichlorobenzoate

Wu-Lan Zeng ^a ^*

^aMicroScale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: wulanzeng@163.com

(Received 8 April 2008; accepted 25 April 2008; online 30 April 2008)

In the title molecule, C₂₄H₁₉Cl₂N₃, the dihedral angles between the benzotriazole group and the ethyl- and dichloro-substituted benzene rings are 16.53 (1) and 82.09 (1)°, respectively. The crystal structure is stabilized by weak intermolecular C—H⋯O interactions.

Related literature

For related literature, see: Chen & Wu (2005 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₄H₁₉Cl₂N₃O₃
M_r = 468.32
Triclinic, $[P \overline 1]$
a = 9.251 (3) Å
b = 10.904 (4) Å
c = 11.057 (4) Å
α = 88.327 (6)°
β = 86.442 (6)°
γ = 83.304 (5)°
V = 1105.4 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 298 (2) K
0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.938, T_max = 0.991
5375 measured reflections
3700 independent reflections
2701 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.124
S = 1.03
3700 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O3ⁱ	0.93	2.51	3.425 (3)	169
C12—H12A⋯O1ⁱⁱ	0.93	2.52	3.378 (4)	154
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x+1, y, z.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011951/lh2614sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808011951/lh2614Isup2.hkl

checkCIF report

Comment top

1H-Benzotriazole and its derivatives are an important class of compounds because they exhibit a broad spectrum of pharmacological activities such as antifungal, antitumor and antineoplastic activities (Chen & Wu, 2005). All bond lengths and angles in the title molecule (I) are within normal ranges (Allen et al., 1987). The benzotriazole ring system is essentially planar, with a dihedral angle of 1.05 (1)° between the triazole ring (atoms N1—N3/C10/C16) and the benzene ring (C10—C16). The dihedral angles between the mean planes of the benzotriazole system and ring atoms C1—C6 and C17—C22 are 82.09 (1) and 16.53 (1), respectively. The dihedral angle between rings atoms C1—C6 and C17—C22 is 89.47 (2). In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) link molecules into chains extended along the a axis.

Related literature top

For related literature, see: Chen & Wu (2005). For bond-length data, see: Allen et al. (1987).

Experimental top

Bromine (3.2 g,0.02 mol) was added dropwise to a solution of 3-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(4-ethylphenyl)propan-1-one (5.58 g,0.02 mol)and sodium acetate(1.6 g,0.02 mol) in acetic acid (50 ml). The reaction proceeded for 7 h. Water (50 ml) and chloroform (20 ml) were then added. The organic layer was washed successively with saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and the chloroform solution filtered. It was cooled with ice-water, and then an acetone solution (10 ml) of 2,4-dichlorobenzoic acid (3.8 g,0.02 mol) and tri ethylamine (2.8 ml) was added. The mixture was stirred with ice-water for about 6 h. The solution was then filtered and concentrated. Single crystals were obtained by slow evaporation of anacetone-ethylacetate(1:1 v/v) solution of (I) at room temperature over a period of one week.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids.
	Fig. 2. Part of the crystal structure of (I) showing hydrogen bonds as dashed lines. Only H atoms involved in hydrogen bonds are shown.

2-(1H-1,2,3-Benzotriazol-1-yl)-1-(4-ethylbenzoyl)ethyl 2,4-dichlorobenzoate top

Crystal data top

C₂₄H₁₉Cl₂N₃O₃	Z = 2
M_r = 468.32	F(000) = 484
Triclinic, P1	D_x = 1.407 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.251 (3) Å	Cell parameters from 3700 reflections
b = 10.904 (4) Å	θ = 1.9–25.0°
c = 11.057 (4) Å	µ = 0.33 mm⁻¹
α = 88.327 (6)°	T = 298 K
β = 86.442 (6)°	Block, colorless
γ = 83.304 (5)°	0.20 × 0.20 × 0.10 mm
V = 1105.4 (6) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3700 independent reflections
Radiation source: fine-focus sealed tube	2701 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −7→10
T_min = 0.938, T_max = 0.991	k = −12→12
5375 measured reflections	l = −10→12

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0528P)² + 0.3617P] where P = (F_o² + 2F_c²)/3
3700 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₄H₁₉Cl₂N₃O₃	γ = 83.304 (5)°
M_r = 468.32	V = 1105.4 (6) Å³
Triclinic, P1	Z = 2
a = 9.251 (3) Å	Mo Kα radiation
b = 10.904 (4) Å	µ = 0.33 mm⁻¹
c = 11.057 (4) Å	T = 298 K
α = 88.327 (6)°	0.20 × 0.20 × 0.10 mm
β = 86.442 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3700 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2701 reflections with I > 2σ(I)
T_min = 0.938, T_max = 0.991	R_int = 0.016
5375 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.03	Δρ_max = 0.26 e Å⁻³
3700 reflections	Δρ_min = −0.34 e Å⁻³
289 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	0.63408 (12)	0.54323 (8)	0.16704 (8)	0.0986 (4)
Cl2	0.17075 (9)	0.52373 (8)	0.46851 (10)	0.0910 (3)
N1	0.5431 (2)	0.10230 (19)	0.83967 (17)	0.0471 (5)
N2	0.4769 (3)	0.1341 (2)	0.9489 (2)	0.0609 (6)
N3	0.5560 (3)	0.2042 (2)	1.0028 (2)	0.0672 (7)
O1	0.1957 (2)	0.28033 (18)	0.58441 (18)	0.0651 (6)
O2	0.41844 (18)	0.18987 (15)	0.61852 (15)	0.0468 (4)
O3	0.3025 (2)	0.01135 (18)	0.51586 (16)	0.0608 (5)
C1	0.5439 (3)	0.4634 (3)	0.2799 (2)	0.0596 (8)
C2	0.4102 (3)	0.5146 (2)	0.3249 (2)	0.0577 (7)
H2B	0.3685	0.5899	0.2942	0.069*
C3	0.3380 (3)	0.4532 (2)	0.4161 (2)	0.0501 (6)
C4	0.4002 (3)	0.3419 (2)	0.4646 (2)	0.0436 (6)
C5	0.5355 (3)	0.2945 (2)	0.4167 (2)	0.0568 (7)
H5A	0.5794	0.2204	0.4483	0.068*
C6	0.6073 (4)	0.3530 (3)	0.3245 (3)	0.0694 (9)
H6A	0.6977	0.3184	0.2924	0.083*
C7	0.3240 (3)	0.2712 (2)	0.5603 (2)	0.0456 (6)
C8	0.3506 (3)	0.1039 (2)	0.6972 (2)	0.0439 (6)
H8A	0.2831	0.1483	0.7571	0.053*
C9	0.4734 (3)	0.0290 (2)	0.7597 (2)	0.0482 (6)
H9A	0.4352	−0.0383	0.8059	0.058*
H9B	0.5452	−0.0065	0.6990	0.058*
C10	0.6686 (3)	0.1556 (2)	0.8221 (2)	0.0431 (6)
C11	0.7727 (3)	0.1540 (2)	0.7266 (2)	0.0503 (6)
H11A	0.7664	0.1095	0.6570	0.060*
C12	0.8851 (3)	0.2213 (3)	0.7409 (3)	0.0601 (8)
H12A	0.9578	0.2228	0.6790	0.072*
C13	0.8951 (3)	0.2882 (3)	0.8449 (3)	0.0700 (9)
H13A	0.9738	0.3331	0.8504	0.084*
C14	0.7928 (4)	0.2892 (3)	0.9380 (3)	0.0692 (8)
H14A	0.7999	0.3340	1.0073	0.083*
C15	0.6762 (3)	0.2204 (2)	0.9264 (2)	0.0538 (7)
C16	0.2697 (3)	0.0221 (2)	0.6232 (2)	0.0431 (6)
C17	0.1553 (3)	−0.0460 (2)	0.6839 (2)	0.0411 (6)
C18	0.0778 (3)	−0.1156 (3)	0.6140 (2)	0.0562 (7)
H18A	0.1012	−0.1206	0.5311	0.067*
C19	−0.0327 (3)	−0.1769 (3)	0.6645 (3)	0.0643 (8)
H19A	−0.0826	−0.2233	0.6154	0.077*
C20	−0.0714 (3)	−0.1716 (3)	0.7863 (3)	0.0584 (7)
C21	0.0066 (3)	−0.1038 (3)	0.8564 (3)	0.0606 (8)
H21A	−0.0172	−0.0997	0.9392	0.073*
C22	0.1188 (3)	−0.0418 (2)	0.8074 (2)	0.0514 (7)
H22A	0.1699	0.0029	0.8572	0.062*
C23	−0.1960 (4)	−0.2369 (3)	0.8398 (4)	0.0919 (12)
H23A	−0.2398	−0.1926	0.9102	0.110*
H23B	−0.2696	−0.2351	0.7808	0.110*
C24	−0.1512 (5)	−0.3659 (4)	0.8759 (4)	0.1279 (18)
H24A	−0.2344	−0.4024	0.9103	0.192*
H24B	−0.0790	−0.3684	0.9349	0.192*
H24C	−0.1110	−0.4112	0.8061	0.192*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1231 (8)	0.0765 (6)	0.0850 (6)	0.0018 (5)	0.0436 (6)	0.0298 (5)
Cl2	0.0503 (5)	0.0744 (5)	0.1377 (8)	0.0148 (4)	0.0167 (5)	0.0406 (5)
N1	0.0510 (13)	0.0529 (12)	0.0360 (11)	−0.0061 (10)	0.0035 (10)	0.0096 (9)
N2	0.0689 (16)	0.0705 (16)	0.0410 (13)	−0.0087 (13)	0.0113 (12)	0.0072 (11)
N3	0.0821 (19)	0.0766 (17)	0.0422 (13)	−0.0113 (15)	0.0051 (13)	0.0002 (12)
O1	0.0416 (12)	0.0720 (13)	0.0788 (14)	−0.0037 (10)	0.0036 (9)	0.0222 (10)
O2	0.0430 (10)	0.0462 (10)	0.0507 (10)	−0.0075 (8)	−0.0010 (8)	0.0142 (8)
O3	0.0685 (13)	0.0705 (13)	0.0441 (11)	−0.0188 (10)	0.0123 (9)	−0.0010 (9)
C1	0.074 (2)	0.0521 (16)	0.0493 (16)	−0.0051 (15)	0.0089 (14)	0.0100 (13)
C2	0.0620 (19)	0.0476 (16)	0.0618 (18)	−0.0022 (14)	−0.0054 (14)	0.0154 (13)
C3	0.0428 (15)	0.0477 (15)	0.0590 (16)	−0.0023 (12)	−0.0059 (12)	0.0075 (12)
C4	0.0450 (14)	0.0429 (14)	0.0434 (14)	−0.0080 (11)	−0.0032 (11)	0.0038 (11)
C5	0.0624 (18)	0.0464 (15)	0.0559 (17)	0.0070 (13)	0.0107 (13)	0.0119 (13)
C6	0.074 (2)	0.0603 (18)	0.0643 (19)	0.0143 (16)	0.0231 (16)	0.0125 (15)
C7	0.0416 (15)	0.0445 (14)	0.0501 (15)	−0.0042 (11)	−0.0027 (12)	0.0037 (12)
C8	0.0447 (15)	0.0441 (14)	0.0419 (13)	−0.0077 (11)	0.0042 (11)	0.0090 (11)
C9	0.0530 (16)	0.0463 (14)	0.0451 (14)	−0.0090 (12)	0.0010 (12)	0.0078 (11)
C10	0.0456 (15)	0.0429 (13)	0.0392 (13)	−0.0006 (11)	−0.0033 (11)	0.0097 (11)
C11	0.0472 (16)	0.0512 (15)	0.0501 (16)	−0.0002 (12)	0.0030 (12)	0.0073 (12)
C12	0.0459 (16)	0.0578 (17)	0.074 (2)	−0.0024 (14)	0.0039 (14)	0.0090 (15)
C13	0.0560 (19)	0.0633 (19)	0.092 (2)	−0.0130 (15)	−0.0131 (18)	0.0106 (18)
C14	0.083 (2)	0.0620 (18)	0.066 (2)	−0.0107 (17)	−0.0198 (18)	−0.0055 (15)
C15	0.0627 (18)	0.0527 (16)	0.0453 (15)	−0.0022 (14)	−0.0088 (13)	0.0043 (12)
C16	0.0414 (14)	0.0424 (13)	0.0429 (15)	0.0001 (11)	0.0055 (11)	0.0058 (11)
C17	0.0401 (14)	0.0385 (13)	0.0428 (14)	−0.0008 (11)	0.0028 (11)	0.0042 (11)
C18	0.0565 (17)	0.0672 (18)	0.0454 (15)	−0.0129 (14)	0.0013 (13)	0.0010 (13)
C19	0.0560 (18)	0.072 (2)	0.068 (2)	−0.0215 (15)	−0.0003 (15)	−0.0026 (15)
C20	0.0497 (17)	0.0519 (16)	0.073 (2)	−0.0095 (13)	0.0081 (14)	0.0057 (14)
C21	0.0667 (19)	0.0624 (18)	0.0506 (16)	−0.0116 (15)	0.0165 (14)	0.0087 (14)
C22	0.0572 (17)	0.0512 (15)	0.0466 (15)	−0.0130 (13)	0.0014 (12)	0.0018 (12)
C23	0.078 (2)	0.094 (3)	0.106 (3)	−0.039 (2)	0.028 (2)	0.000 (2)
C24	0.146 (4)	0.114 (3)	0.137 (4)	−0.077 (3)	−0.020 (3)	0.051 (3)

Geometric parameters (Å, º) top

Cl1—C1	1.729 (3)	C10—C11	1.384 (3)
Cl2—C3	1.720 (3)	C11—C12	1.360 (4)
N1—N2	1.356 (3)	C11—H11A	0.9300
N1—C10	1.358 (3)	C12—C13	1.393 (4)
N1—C9	1.438 (3)	C12—H12A	0.9300
N2—N3	1.298 (3)	C13—C14	1.354 (4)
N3—C15	1.379 (4)	C13—H13A	0.9300
O1—C7	1.194 (3)	C14—C15	1.399 (4)
O2—C7	1.349 (3)	C14—H14A	0.9300
O2—C8	1.432 (3)	C16—C17	1.479 (3)
O3—C16	1.213 (3)	C17—C18	1.384 (4)
C1—C6	1.368 (4)	C17—C22	1.388 (3)
C1—C2	1.366 (4)	C18—C19	1.368 (4)
C2—C3	1.376 (4)	C18—H18A	0.9300
C2—H2B	0.9300	C19—C20	1.372 (4)
C3—C4	1.389 (3)	C19—H19A	0.9300
C4—C5	1.378 (4)	C20—C21	1.376 (4)
C4—C7	1.482 (3)	C20—C23	1.506 (4)
C5—C6	1.365 (4)	C21—C22	1.378 (4)
C5—H5A	0.9300	C21—H21A	0.9300
C6—H6A	0.9300	C22—H22A	0.9300
C8—C9	1.511 (3)	C23—C24	1.471 (5)
C8—C16	1.517 (3)	C23—H23A	0.9700
C8—H8A	0.9800	C23—H23B	0.9700
C9—H9A	0.9700	C24—H24A	0.9600
C9—H9B	0.9700	C24—H24B	0.9600
C10—C15	1.379 (4)	C24—H24C	0.9600

N2—N1—C10	109.9 (2)	C11—C12—C13	122.3 (3)
N2—N1—C9	119.9 (2)	C11—C12—H12A	118.9
C10—N1—C9	130.1 (2)	C13—C12—H12A	118.9
N3—N2—N1	109.1 (2)	C14—C13—C12	121.5 (3)
N2—N3—C15	107.8 (2)	C14—C13—H13A	119.2
C7—O2—C8	114.28 (19)	C12—C13—H13A	119.2
C6—C1—C2	121.2 (3)	C13—C14—C15	117.6 (3)
C6—C1—Cl1	120.3 (2)	C13—C14—H14A	121.2
C2—C1—Cl1	118.4 (2)	C15—C14—H14A	121.2
C1—C2—C3	119.2 (2)	N3—C15—C10	108.8 (2)
C1—C2—H2B	120.4	N3—C15—C14	131.5 (3)
C3—C2—H2B	120.4	C10—C15—C14	119.7 (3)
C2—C3—C4	121.0 (2)	O3—C16—C17	121.2 (2)
C2—C3—Cl2	116.5 (2)	O3—C16—C8	119.3 (2)
C4—C3—Cl2	122.5 (2)	C17—C16—C8	119.5 (2)
C5—C4—C3	117.6 (2)	C18—C17—C22	117.9 (2)
C5—C4—C7	119.7 (2)	C18—C17—C16	118.7 (2)
C3—C4—C7	122.7 (2)	C22—C17—C16	123.4 (2)
C6—C5—C4	122.1 (2)	C19—C18—C17	121.2 (3)
C6—C5—H5A	119.0	C19—C18—H18A	119.4
C4—C5—H5A	119.0	C17—C18—H18A	119.4
C5—C6—C1	118.9 (3)	C18—C19—C20	121.3 (3)
C5—C6—H6A	120.6	C18—C19—H19A	119.3
C1—C6—H6A	120.6	C20—C19—H19A	119.3
O1—C7—O2	122.2 (2)	C19—C20—C21	117.6 (3)
O1—C7—C4	126.3 (2)	C19—C20—C23	120.6 (3)
O2—C7—C4	111.5 (2)	C21—C20—C23	121.7 (3)
O2—C8—C9	105.67 (19)	C22—C21—C20	122.0 (3)
O2—C8—C16	109.74 (19)	C22—C21—H21A	119.0
C9—C8—C16	111.0 (2)	C20—C21—H21A	119.0
O2—C8—H8A	110.1	C21—C22—C17	119.9 (3)
C9—C8—H8A	110.1	C21—C22—H22A	120.0
C16—C8—H8A	110.1	C17—C22—H22A	120.0
N1—C9—C8	112.2 (2)	C24—C23—C20	113.1 (3)
N1—C9—H9A	109.2	C24—C23—H23A	109.0
C8—C9—H9A	109.2	C20—C23—H23A	109.0
N1—C9—H9B	109.2	C24—C23—H23B	109.0
C8—C9—H9B	109.2	C20—C23—H23B	109.0
H9A—C9—H9B	107.9	H23A—C23—H23B	107.8
N1—C10—C15	104.4 (2)	C23—C24—H24A	109.5
N1—C10—C11	132.5 (2)	C23—C24—H24B	109.5
C15—C10—C11	123.0 (3)	H24A—C24—H24B	109.5
C12—C11—C10	115.9 (3)	C23—C24—H24C	109.5
C12—C11—H11A	122.1	H24A—C24—H24C	109.5
C10—C11—H11A	122.1	H24B—C24—H24C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O3ⁱ	0.93	2.51	3.425 (3)	169
C12—H12A···O1ⁱⁱ	0.93	2.52	3.378 (4)	154

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

Experimental details

Crystal data
Chemical formula	C₂₄H₁₉Cl₂N₃O₃
M_r	468.32
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.251 (3), 10.904 (4), 11.057 (4)
α, β, γ (°)	88.327 (6), 86.442 (6), 83.304 (5)
V (Å³)	1105.4 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.938, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	5375, 3700, 2701
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.124, 1.03
No. of reflections	3700
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.34

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O3ⁱ	0.93	2.51	3.425 (3)	169
C12—H12A···O1ⁱⁱ	0.93	2.52	3.378 (4)	154

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

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Z.-Y. & Wu, M.-J. (2005). Org. Lett. 7, 475–477. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 5| May 2008| Page o942

doi:10.1107/S1600536808011951

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