2-(1H-Benzotriazol-1-yl)-1-(3-methyl­benzo­yl)ethyl benzoate

Zeng, W.-L.; Du, L.-C.; Zhang, L.; Jian, F.-F.

doi:10.1107/S1600536809026853

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1882

doi:10.1107/S1600536809026853

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2-(1H-Benzotriazol-1-yl)-1-(3-methylbenzoyl)ethyl benzoate

Wu-Lan Zeng,^a Lian-Cai Du,^b Lei Zhang ^b and Fang-Fang Jian ^b ^*

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

(Received 7 June 2009; accepted 9 July 2009; online 18 July 2009)

In the title molecule, C₂₃H₁₉N₃O₃, the dihedral angles between the mean plane of the benzotriazole ring system and the benzene and phenyl rings are 9.67 (9) and 86.08 (10)°, respectively. The dihedral angle between the benzene and phenyl rings is 85.89 (11)°. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link molecules into chains along [010].

Related literature

For the pharmacological activities of 1H-benzotriazoles and their derivatives, see: Chen & Wu (2005 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₃H₁₉N₃O₃
M_r = 385.41
Monoclinic, P 2₁ /c
a = 10.1095 (5) Å
b = 9.3849 (4) Å
c = 20.7091 (10) Å
β = 99.061 (4)°
V = 1940.29 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.30 × 0.10 × 0.10 mm

Data collection

Siemens SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.974, T_max = 0.991
16102 measured reflections
3301 independent reflections
2071 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.110
S = 1.00
3301 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O2ⁱ	0.97	2.42	3.062 (2)	123
C11—H11A⋯O1ⁱⁱ	0.93	2.60	3.375 (2)	141
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026853/lh2841sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809026853/lh2841Isup2.hkl

checkCIF report

Comment top

1H-Benzotriazoles and their 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). Herein, we present the crystal structure of the title compound (I). In (I) (Fig. 1) all bond lengths (Allen et al., 1987) and angles within normal ranges. The benzotriazole ring system is essentially planar. The dihedral angles between the mean plane of the benzotriazole ring system and rings C10—C15 and C18—C23 are 9.67 (9) and 86.08 (10)°, respectively. The dihedral angle between rings C10—C15 and C19—C23 is 85.89 (11)°. In the crystal structure weak intermolecular C—H···O hydrogen bonds link molecules into chains along [010] (see Fig. 2).

Related literature top

For the pharmacological activities of 1H-benzotriazoles and their derivatives, see: Chen & Wu (2005). For standard 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-m-tolylpropan-1-one (5.30 g,0.02 mol) and sodium acetate (1.6 g,0.02 mol) in acetic acid (50 ml). The reaction proceeded for 8 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 anhydrou magnesium sulfate and the chloroform solution filtered. It was cooled with ice-water, and then an acetone solution (10 ml) of benzoic acid (2.24 g,0.02 mol) and triethylamine (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 an acetone-ethylacetate (1:1 v/v) solution of (I) at room temperature over a period of one week.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); 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 with hydrogen bonds shown as dashed lines.

2-(1H-Benzotriazol-1-yl)-1-(3-methylbenzoyl)ethyl benzoate top

Crystal data top

C₂₃H₁₉N₃O₃	F(000) = 808
M_r = 385.41	D_x = 1.319 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3301 reflections
a = 10.1095 (5) Å	θ = 2.0–25.0°
b = 9.3849 (4) Å	µ = 0.09 mm⁻¹
c = 20.7091 (10) Å	T = 298 K
β = 99.061 (4)°	Block, colorless
V = 1940.29 (16) Å³	0.30 × 0.10 × 0.10 mm
Z = 4

Data collection top

Siemens SMART CCD diffractometer	3301 independent reflections
Radiation source: fine-focus sealed tube	2071 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.974, T_max = 0.991	k = −11→11
16102 measured reflections	l = −23→24

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0483P)² + 0.2024P] where P = (F_o² + 2F_c²)/3
3301 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₃H₁₉N₃O₃	V = 1940.29 (16) Å³
M_r = 385.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.1095 (5) Å	µ = 0.09 mm⁻¹
b = 9.3849 (4) Å	T = 298 K
c = 20.7091 (10) Å	0.30 × 0.10 × 0.10 mm
β = 99.061 (4)°

Data collection top

Siemens SMART CCD diffractometer	3301 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2071 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.991	R_int = 0.051
16102 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.00	Δρ_max = 0.19 e Å⁻³
3301 reflections	Δρ_min = −0.22 e Å⁻³
262 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
O1	0.09785 (14)	0.45987 (15)	0.21346 (7)	0.0543 (4)
O2	0.17138 (13)	0.14124 (15)	0.23494 (7)	0.0508 (4)
O3	0.18369 (12)	0.29378 (14)	0.31866 (6)	0.0444 (4)
C1	0.0844 (2)	0.2945 (3)	0.51412 (11)	0.0562 (6)
C2	0.1674 (3)	0.2855 (3)	0.57479 (12)	0.0757 (8)
H2B	0.1432	0.2312	0.6086	0.091*
C3	0.2831 (3)	0.3582 (4)	0.58230 (14)	0.0886 (10)
H3A	0.3400	0.3535	0.6222	0.106*
C4	0.3204 (3)	0.4402 (3)	0.53236 (16)	0.0884 (9)
H4A	0.4022	0.4876	0.5397	0.106*
C5	0.2409 (3)	0.4538 (3)	0.47244 (13)	0.0677 (7)
H5A	0.2654	0.5103	0.4394	0.081*
C6	0.1216 (2)	0.3781 (2)	0.46443 (10)	0.0464 (5)
C7	−0.0004 (2)	0.4194 (2)	0.34864 (9)	0.0518 (6)
H7A	0.0510	0.5066	0.3485	0.062*
H7B	−0.0943	0.4431	0.3358	0.062*
C8	0.04164 (19)	0.3168 (2)	0.29917 (9)	0.0431 (5)
H8A	−0.0068	0.2265	0.3000	0.052*
C9	0.0140 (2)	0.3818 (2)	0.23043 (9)	0.0402 (5)
C10	−0.11527 (19)	0.3540 (2)	0.18760 (9)	0.0391 (5)
C11	−0.2093 (2)	0.2566 (2)	0.20324 (11)	0.0521 (6)
H11A	−0.1922	0.2043	0.2418	0.062*
C12	−0.3285 (2)	0.2383 (3)	0.16091 (12)	0.0634 (7)
H12A	−0.3912	0.1729	0.1711	0.076*
C13	−0.3551 (2)	0.3158 (2)	0.10391 (11)	0.0586 (6)
H13A	−0.4359	0.3025	0.0762	0.070*
C14	−0.2632 (2)	0.4134 (2)	0.08716 (10)	0.0479 (5)
C15	−0.1438 (2)	0.4296 (2)	0.12935 (10)	0.0442 (5)
H15A	−0.0804	0.4932	0.1184	0.053*
C16	−0.2919 (3)	0.4998 (3)	0.02543 (11)	0.0743 (8)
H16A	−0.3786	0.4747	0.0022	0.112*
H16B	−0.2250	0.4804	−0.0015	0.112*
H16C	−0.2905	0.5993	0.0362	0.112*
C17	0.2376 (2)	0.1978 (2)	0.28153 (10)	0.0395 (5)
C18	0.38089 (19)	0.1709 (2)	0.30448 (9)	0.0412 (5)
C19	0.4567 (2)	0.2509 (2)	0.35264 (11)	0.0599 (7)
H19A	0.4178	0.3263	0.3720	0.072*
C20	0.5906 (2)	0.2187 (3)	0.37213 (12)	0.0713 (8)
H20A	0.6414	0.2733	0.4044	0.086*
C21	0.6490 (2)	0.1080 (3)	0.34462 (12)	0.0637 (7)
H21A	0.7390	0.0871	0.3581	0.076*
C22	0.5745 (2)	0.0282 (3)	0.29719 (12)	0.0604 (6)
H22A	0.6140	−0.0479	0.2787	0.072*
C23	0.4409 (2)	0.0590 (2)	0.27624 (11)	0.0514 (6)
H23A	0.3915	0.0049	0.2433	0.062*
N1	−0.0359 (2)	0.2318 (2)	0.49227 (10)	0.0793 (7)
N2	−0.07420 (19)	0.2723 (2)	0.43222 (10)	0.0730 (6)
N3	0.01911 (17)	0.36109 (19)	0.41419 (8)	0.0487 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0460 (9)	0.0623 (10)	0.0531 (10)	−0.0116 (8)	0.0031 (7)	0.0094 (8)
O2	0.0483 (9)	0.0567 (9)	0.0447 (9)	−0.0043 (7)	−0.0009 (7)	−0.0106 (8)
O3	0.0398 (8)	0.0517 (9)	0.0394 (8)	0.0079 (7)	−0.0005 (6)	−0.0068 (7)
C1	0.0569 (15)	0.0742 (17)	0.0380 (14)	0.0125 (13)	0.0090 (12)	0.0009 (12)
C2	0.085 (2)	0.102 (2)	0.0395 (15)	0.0252 (18)	0.0090 (14)	0.0056 (14)
C3	0.078 (2)	0.136 (3)	0.0470 (18)	0.021 (2)	−0.0036 (16)	−0.0203 (18)
C4	0.0663 (18)	0.119 (3)	0.076 (2)	−0.0130 (17)	−0.0001 (17)	−0.040 (2)
C5	0.0687 (17)	0.0741 (17)	0.0603 (17)	−0.0128 (14)	0.0101 (14)	−0.0133 (14)
C6	0.0483 (13)	0.0536 (14)	0.0371 (13)	0.0106 (11)	0.0059 (11)	−0.0030 (11)
C7	0.0539 (14)	0.0633 (15)	0.0375 (13)	0.0198 (11)	0.0047 (11)	0.0069 (11)
C8	0.0360 (12)	0.0521 (13)	0.0397 (13)	0.0054 (10)	0.0008 (9)	0.0040 (10)
C9	0.0402 (12)	0.0422 (12)	0.0382 (12)	0.0050 (10)	0.0055 (10)	−0.0008 (10)
C10	0.0384 (12)	0.0415 (12)	0.0371 (12)	0.0015 (9)	0.0046 (9)	−0.0018 (10)
C11	0.0444 (13)	0.0583 (14)	0.0517 (14)	−0.0003 (11)	0.0021 (11)	0.0108 (11)
C12	0.0461 (14)	0.0701 (17)	0.0704 (18)	−0.0134 (12)	−0.0017 (12)	0.0155 (14)
C13	0.0472 (14)	0.0683 (16)	0.0547 (15)	−0.0041 (12)	−0.0090 (11)	−0.0019 (13)
C14	0.0500 (14)	0.0533 (14)	0.0389 (13)	0.0071 (11)	0.0021 (11)	−0.0007 (10)
C15	0.0403 (12)	0.0511 (14)	0.0405 (13)	−0.0014 (10)	0.0039 (10)	0.0014 (10)
C16	0.0744 (18)	0.092 (2)	0.0504 (15)	0.0029 (14)	−0.0092 (13)	0.0170 (14)
C17	0.0450 (13)	0.0398 (12)	0.0332 (12)	−0.0006 (10)	0.0045 (10)	0.0024 (10)
C18	0.0416 (12)	0.0432 (12)	0.0391 (12)	0.0001 (10)	0.0072 (10)	0.0032 (10)
C19	0.0476 (14)	0.0673 (16)	0.0611 (16)	0.0089 (12)	−0.0033 (12)	−0.0190 (13)
C20	0.0485 (15)	0.0864 (19)	0.0734 (18)	0.0059 (14)	−0.0077 (13)	−0.0231 (15)
C21	0.0421 (14)	0.0818 (18)	0.0669 (17)	0.0119 (13)	0.0079 (13)	0.0018 (15)
C22	0.0508 (15)	0.0639 (16)	0.0683 (17)	0.0132 (12)	0.0151 (13)	−0.0050 (13)
C23	0.0490 (14)	0.0518 (14)	0.0538 (14)	0.0006 (11)	0.0094 (11)	−0.0057 (11)
N1	0.0728 (15)	0.1137 (19)	0.0527 (14)	−0.0127 (14)	0.0142 (12)	0.0184 (13)
N2	0.0516 (12)	0.1129 (18)	0.0558 (14)	−0.0102 (12)	0.0118 (10)	0.0085 (13)
N3	0.0431 (11)	0.0660 (13)	0.0367 (11)	0.0073 (9)	0.0057 (9)	0.0051 (9)

Geometric parameters (Å, º) top

O1—C9	1.213 (2)	C11—H11A	0.9300
O2—C17	1.207 (2)	C12—C13	1.377 (3)
O3—C17	1.353 (2)	C12—H12A	0.9300
O3—C8	1.445 (2)	C13—C14	1.387 (3)
C1—N1	1.363 (3)	C13—H13A	0.9300
C1—C6	1.392 (3)	C14—C15	1.382 (3)
C1—C2	1.399 (3)	C14—C16	1.503 (3)
C2—C3	1.342 (4)	C15—H15A	0.9300
C2—H2B	0.9300	C16—H16A	0.9600
C3—C4	1.388 (4)	C16—H16B	0.9600
C3—H3A	0.9300	C16—H16C	0.9600
C4—C5	1.374 (4)	C17—C18	1.474 (3)
C4—H4A	0.9300	C18—C19	1.380 (3)
C5—C6	1.387 (3)	C18—C23	1.387 (3)
C5—H5A	0.9300	C19—C20	1.384 (3)
C6—N3	1.357 (2)	C19—H19A	0.9300
C7—N3	1.448 (2)	C20—C21	1.363 (3)
C7—C8	1.515 (3)	C20—H20A	0.9300
C7—H7A	0.9700	C21—C22	1.364 (3)
C7—H7B	0.9700	C21—H21A	0.9300
C8—C9	1.534 (3)	C22—C23	1.382 (3)
C8—H8A	0.9800	C22—H22A	0.9300
C9—C10	1.482 (3)	C23—H23A	0.9300
C10—C15	1.390 (3)	N1—N2	1.300 (3)
C10—C11	1.393 (3)	N2—N3	1.355 (2)
C11—C12	1.385 (3)

C17—O3—C8	114.33 (15)	C11—C12—H12A	119.7
N1—C1—C6	109.2 (2)	C12—C13—C14	121.0 (2)
N1—C1—C2	130.5 (2)	C12—C13—H13A	119.5
C6—C1—C2	120.3 (2)	C14—C13—H13A	119.5
C3—C2—C1	117.5 (3)	C15—C14—C13	117.8 (2)
C3—C2—H2B	121.3	C15—C14—C16	120.7 (2)
C1—C2—H2B	121.3	C13—C14—C16	121.4 (2)
C2—C3—C4	122.0 (3)	C14—C15—C10	122.27 (19)
C2—C3—H3A	119.0	C14—C15—H15A	118.9
C4—C3—H3A	119.0	C10—C15—H15A	118.9
C5—C4—C3	122.4 (3)	C14—C16—H16A	109.5
C5—C4—H4A	118.8	C14—C16—H16B	109.5
C3—C4—H4A	118.8	H16A—C16—H16B	109.5
C4—C5—C6	115.8 (2)	C14—C16—H16C	109.5
C4—C5—H5A	122.1	H16A—C16—H16C	109.5
C6—C5—H5A	122.1	H16B—C16—H16C	109.5
N3—C6—C5	134.1 (2)	O2—C17—O3	121.65 (18)
N3—C6—C1	103.80 (19)	O2—C17—C18	125.15 (19)
C5—C6—C1	122.1 (2)	O3—C17—C18	113.20 (17)
N3—C7—C8	112.51 (16)	C19—C18—C23	119.12 (19)
N3—C7—H7A	109.1	C19—C18—C17	123.06 (19)
C8—C7—H7A	109.1	C23—C18—C17	117.82 (18)
N3—C7—H7B	109.1	C18—C19—C20	119.9 (2)
C8—C7—H7B	109.1	C18—C19—H19A	120.1
H7A—C7—H7B	107.8	C20—C19—H19A	120.1
O3—C8—C7	106.18 (16)	C21—C20—C19	120.8 (2)
O3—C8—C9	110.28 (15)	C21—C20—H20A	119.6
C7—C8—C9	110.21 (16)	C19—C20—H20A	119.6
O3—C8—H8A	110.0	C22—C21—C20	119.5 (2)
C7—C8—H8A	110.0	C22—C21—H21A	120.2
C9—C8—H8A	110.0	C20—C21—H21A	120.2
O1—C9—C10	121.57 (18)	C21—C22—C23	120.9 (2)
O1—C9—C8	118.38 (18)	C21—C22—H22A	119.6
C10—C9—C8	119.99 (18)	C23—C22—H22A	119.6
C15—C10—C11	118.72 (19)	C22—C23—C18	119.8 (2)
C15—C10—C9	118.17 (18)	C22—C23—H23A	120.1
C11—C10—C9	123.11 (18)	C18—C23—H23A	120.1
C12—C11—C10	119.5 (2)	N2—N1—C1	107.9 (2)
C12—C11—H11A	120.3	N1—N2—N3	109.15 (19)
C10—C11—H11A	120.3	C6—N3—N2	109.98 (17)
C13—C12—C11	120.7 (2)	C6—N3—C7	130.49 (19)
C13—C12—H12A	119.7	N2—N3—C7	119.52 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O2ⁱ	0.97	2.42	3.062 (2)	123
C11—H11A···O1ⁱⁱ	0.93	2.60	3.375 (2)	141

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

Experimental details

Crystal data
Chemical formula	C₂₃H₁₉N₃O₃
M_r	385.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.1095 (5), 9.3849 (4), 20.7091 (10)
β (°)	99.061 (4)
V (Å³)	1940.29 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Siemens SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.974, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	16102, 3301, 2071
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.110, 1.00
No. of reflections	3301
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.22

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O2ⁱ	0.97	2.42	3.062 (2)	123
C11—H11A···O1ⁱⁱ	0.93	2.60	3.375 (2)	141

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

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
Chen, Z.-Y. & Wu, M.-J. (2005). Org. Lett. 7, 475–477. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. 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 8| August 2009| Page o1882

doi:10.1107/S1600536809026853

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