Ethyl 2-benzyl-1-propyl-1H-indole-3-carboxyl­ate

Li, P.; Wang, W.; Li, C.; Bian, X.

doi:10.1107/S1600536809016493

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1284

doi:10.1107/S1600536809016493

Open

access

Ethyl 2-benzyl-1-propyl-1H-indole-3-carboxylate

Peifan Li,^a ^* Wenjie Wang,^a Caiyun Li ^a and Xiaoxia Bian ^a

^aDepartment of Pharmaceuticals, Tianjin Medical College, Tianjin 300222, People's Republic of China
^*Correspondence e-mail: austinmm@126.com

(Received 29 April 2009; accepted 2 May 2009; online 14 May 2009)

In the title compound, C₂₁H₂₃NO₂, the dihedral angle between the indole ring system and the benzyl ring is 75.92 (9)°. The crystal packing is controlled by C—H⋯O and C—H⋯π interactions.

Related literature

For the synthesis of the title compound, see: Du et al. (2006 ). For its precursor, see: Jin et al. (2009 ).

Experimental

Crystal data

C₂₁H₂₃NO₂
M_r = 321.40
Orthorhombic, P n a 2₁
a = 16.231 (3) Å
b = 19.479 (4) Å
c = 5.5226 (11) Å
V = 1746.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 113 K
0.20 × 0.16 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.985, T_max = 0.991
13765 measured reflections
2204 independent reflections
2060 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.102
S = 1.07
2204 reflections
220 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.95	2.71	3.653 (3)	173
C9—H9B⋯O1ⁱ	0.99	2.88	3.680 (3)	138
C11—H11A⋯O1ⁱ	0.98	2.69	3.514 (3)	142
C12—H12A⋯O1	0.99	2.39	3.044 (3)	123
C18—H18⋯O1	0.95	2.96	3.620 (3)	128
C21—H21A⋯O2ⁱⁱ	0.98	2.91	3.555 (3)	124
C3—H3⋯Cgⁱⁱⁱ	0.95	2.82	3.632 (3)	144
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (ii) $[-x+1, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-1]$ . Cg is the centroid of the C13–C18 ring.

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2005).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809016493/hb2963sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809016493/hb2963Isup2.hkl

checkCIF report

Comment top

Indole chemistry continue to capture the attention of synthetic organic chemists due to indole's pharmaceutical properties. Recently we have reported the crystal structure of (Z)-ethyl 2,4-diphenyl-3-(propylamino)-but-2-enoate(Jin et al., 2009). Starting from this precursor, its indole derivative was prepared according to the method of Du and coworkers. To further study the SAR, we determine the crystal structure of this indole derivative.

In the molecular structure,(I)(Fig. 1), the indole ring is coplanar with a dihedral angle of 0.21 (12)° between its pyrrole ring and fused benzene ring. The indole ring forms an angle of 75.92 (9)° with the benzyl ring.

Related literature top

For the synthesis of the title compound, see: Du et al. (2006). For its precursor, see: Jin et al. (2009). Cg is the centroid of the C13–C18 ring.

Experimental top

The title compound was prepared according to the method of the literature (Du et al., 2006). The crystals fit for X-ray diffraction were grown from a mixture of ethyl actate and petroleum ether.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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: CrystalStructure (Rigaku/MSC, 2005).

Figures top

Fig. 1. The molecular structure of molecule one of (I) with the atom-numbering scheme and 50% probability displacement ellipsoids.

Ethyl 2-benzyl-1-propyl-1H-indole-3-carboxylate top

Crystal data top

C₂₁H₂₃NO₂	F(000) = 688
M_r = 321.40	D_x = 1.223 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5126 reflections
a = 16.231 (3) Å	θ = 2.4–27.5°
b = 19.479 (4) Å	µ = 0.08 mm⁻¹
c = 5.5226 (11) Å	T = 113 K
V = 1746.0 (6) Å³	Needle, colourless
Z = 4	0.20 × 0.16 × 0.12 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2204 independent reflections
Radiation source: rotating anode	2060 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.044
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.5°, θ_min = 2.4°
ω and ϕ scans	h = −21→20
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −25→25
T_min = 0.985, T_max = 0.991	l = −4→7
13765 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)] = 0.044	H-atom parameters constrained
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.0496P)² + 0.3147P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2204 reflections	Δρ_max = 0.18 e Å⁻³
220 parameters	Δρ_min = −0.15 e Å⁻³
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.044 (4)

Crystal data top

C₂₁H₂₃NO₂	V = 1746.0 (6) Å³
M_r = 321.40	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 16.231 (3) Å	µ = 0.08 mm⁻¹
b = 19.479 (4) Å	T = 113 K
c = 5.5226 (11) Å	0.20 × 0.16 × 0.12 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2204 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2060 reflections with I > 2σ(I)
T_min = 0.985, T_max = 0.991	R_int = 0.044
13765 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	1 restraint
wR(F²) = 0.102	H-atom parameters constrained
S = 1.07	Δρ_max = 0.18 e Å⁻³
2204 reflections	Δρ_min = −0.15 e Å⁻³
220 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	0.38761 (9)	0.34048 (8)	0.2851 (4)	0.0430 (5)
O2	0.45086 (8)	0.40505 (7)	0.0042 (3)	0.0357 (4)
N1	0.62712 (10)	0.24714 (8)	0.3130 (4)	0.0294 (4)
C1	0.66004 (12)	0.28279 (10)	0.1183 (4)	0.0300 (5)
C2	0.73763 (13)	0.27623 (11)	0.0133 (5)	0.0355 (5)
H2	0.7768	0.2440	0.0718	0.043*
C3	0.75495 (13)	0.31898 (11)	−0.1805 (5)	0.0392 (6)
H3	0.8075	0.3164	−0.2557	0.047*
C4	0.69695 (14)	0.36590 (11)	−0.2680 (5)	0.0383 (6)
H4	0.7107	0.3941	−0.4023	0.046*
C5	0.62019 (13)	0.37209 (10)	−0.1635 (5)	0.0339 (5)
H5	0.5813	0.4042	−0.2245	0.041*
C6	0.60052 (12)	0.33007 (10)	0.0348 (4)	0.0288 (4)
C7	0.52909 (13)	0.32030 (9)	0.1883 (4)	0.0288 (5)
C8	0.54835 (12)	0.26987 (10)	0.3565 (5)	0.0290 (4)
C9	0.67057 (12)	0.19227 (10)	0.4394 (5)	0.0326 (5)
H9A	0.6472	0.1873	0.6041	0.039*
H9B	0.7293	0.2052	0.4568	0.039*
C10	0.66510 (12)	0.12335 (10)	0.3092 (5)	0.0336 (5)
H10A	0.6066	0.1103	0.2890	0.040*
H10B	0.6901	0.1273	0.1464	0.040*
C11	0.70976 (14)	0.06838 (11)	0.4534 (5)	0.0404 (6)
H11A	0.7673	0.0821	0.4774	0.061*
H11B	0.7079	0.0248	0.3647	0.061*
H11C	0.6830	0.0627	0.6112	0.061*
C12	0.49933 (13)	0.24338 (10)	0.5656 (4)	0.0315 (5)
H12A	0.4530	0.2753	0.5963	0.038*
H12B	0.5348	0.2433	0.7115	0.038*
C13	0.46466 (12)	0.17145 (10)	0.5295 (4)	0.0271 (4)
C14	0.47834 (13)	0.12068 (10)	0.7011 (4)	0.0317 (5)
H14	0.5121	0.1302	0.8376	0.038*
C15	0.44300 (14)	0.05585 (11)	0.6750 (5)	0.0360 (5)
H15	0.4527	0.0214	0.7933	0.043*
C16	0.39379 (13)	0.04180 (11)	0.4763 (5)	0.0350 (5)
H16	0.3692	−0.0022	0.4589	0.042*
C17	0.38041 (13)	0.09212 (10)	0.3027 (5)	0.0331 (5)
H17	0.3470	0.0825	0.1656	0.040*
C18	0.41579 (12)	0.15656 (10)	0.3295 (4)	0.0296 (4)
H18	0.4065	0.1908	0.2100	0.036*
C19	0.44951 (13)	0.35436 (10)	0.1705 (4)	0.0308 (5)
C20	0.37460 (14)	0.44182 (11)	−0.0340 (6)	0.0410 (6)
H20A	0.3565	0.4641	0.1180	0.049*
H20B	0.3308	0.4099	−0.0879	0.049*
C21	0.39091 (15)	0.49475 (12)	−0.2251 (5)	0.0442 (6)
H21A	0.4351	0.5254	−0.1710	0.066*
H21B	0.3407	0.5215	−0.2539	0.066*
H21C	0.4076	0.4719	−0.3755	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0300 (8)	0.0423 (8)	0.0567 (13)	0.0019 (6)	0.0131 (9)	0.0115 (9)
O2	0.0274 (7)	0.0368 (8)	0.0430 (10)	−0.0020 (6)	0.0009 (8)	0.0075 (8)
N1	0.0260 (8)	0.0311 (8)	0.0312 (10)	−0.0032 (6)	0.0012 (8)	−0.0027 (8)
C1	0.0266 (10)	0.0306 (9)	0.0327 (12)	−0.0088 (8)	0.0015 (9)	−0.0073 (9)
C2	0.0254 (10)	0.0386 (10)	0.0426 (14)	−0.0055 (8)	0.0034 (10)	−0.0085 (10)
C3	0.0303 (11)	0.0443 (11)	0.0430 (15)	−0.0113 (9)	0.0102 (11)	−0.0075 (12)
C4	0.0378 (12)	0.0397 (11)	0.0375 (14)	−0.0123 (9)	0.0062 (11)	−0.0025 (11)
C5	0.0336 (11)	0.0316 (9)	0.0365 (12)	−0.0097 (8)	0.0031 (10)	−0.0032 (10)
C6	0.0280 (10)	0.0285 (9)	0.0299 (11)	−0.0067 (7)	0.0022 (9)	−0.0053 (9)
C7	0.0274 (10)	0.0270 (9)	0.0319 (12)	−0.0055 (7)	0.0028 (9)	−0.0027 (9)
C8	0.0268 (10)	0.0302 (9)	0.0299 (11)	−0.0059 (8)	0.0008 (9)	−0.0049 (9)
C9	0.0292 (10)	0.0361 (10)	0.0325 (12)	−0.0017 (8)	−0.0030 (10)	−0.0023 (10)
C10	0.0289 (10)	0.0353 (10)	0.0366 (13)	−0.0010 (8)	−0.0005 (10)	−0.0015 (10)
C11	0.0380 (12)	0.0375 (11)	0.0457 (14)	−0.0001 (9)	−0.0005 (12)	0.0050 (11)
C12	0.0324 (10)	0.0342 (10)	0.0278 (12)	−0.0020 (8)	0.0032 (9)	−0.0037 (9)
C13	0.0231 (9)	0.0308 (9)	0.0273 (11)	0.0012 (7)	0.0046 (8)	−0.0017 (9)
C14	0.0288 (10)	0.0400 (10)	0.0262 (11)	−0.0006 (9)	0.0007 (9)	0.0025 (10)
C15	0.0359 (11)	0.0382 (11)	0.0338 (12)	0.0039 (9)	0.0005 (10)	0.0059 (10)
C16	0.0388 (11)	0.0308 (9)	0.0352 (13)	−0.0024 (8)	0.0057 (10)	−0.0003 (10)
C17	0.0336 (11)	0.0373 (10)	0.0283 (12)	−0.0038 (8)	−0.0018 (10)	−0.0016 (10)
C18	0.0306 (10)	0.0313 (9)	0.0271 (11)	−0.0001 (8)	0.0008 (9)	0.0017 (9)
C19	0.0292 (10)	0.0280 (9)	0.0353 (12)	−0.0052 (8)	0.0025 (10)	−0.0018 (9)
C20	0.0327 (11)	0.0392 (11)	0.0512 (16)	0.0003 (9)	0.0010 (11)	0.0093 (12)
C21	0.0441 (13)	0.0411 (11)	0.0474 (16)	−0.0055 (10)	−0.0029 (12)	0.0099 (12)

Geometric parameters (Å, º) top

O1—C19	1.218 (3)	C10—H10B	0.9900
O2—C19	1.349 (3)	C11—H11A	0.9800
O2—C20	1.446 (3)	C11—H11B	0.9800
N1—C8	1.374 (3)	C11—H11C	0.9800
N1—C1	1.387 (3)	C12—C13	1.523 (3)
N1—C9	1.458 (3)	C12—H12A	0.9900
C1—C2	1.392 (3)	C12—H12B	0.9900
C1—C6	1.412 (3)	C13—C14	1.387 (3)
C2—C3	1.385 (4)	C13—C18	1.391 (3)
C2—H2	0.9500	C14—C15	1.394 (3)
C3—C4	1.398 (3)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.384 (3)
C4—C5	1.378 (3)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.388 (3)
C5—C6	1.404 (3)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.388 (3)
C6—C7	1.449 (3)	C17—H17	0.9500
C7—C8	1.388 (3)	C18—H18	0.9500
C7—C19	1.455 (3)	C20—C21	1.499 (4)
C8—C12	1.494 (3)	C20—H20A	0.9900
C9—C10	1.526 (3)	C20—H20B	0.9900
C9—H9A	0.9900	C21—H21A	0.9800
C9—H9B	0.9900	C21—H21B	0.9800
C10—C11	1.518 (3)	C21—H21C	0.9800
C10—H10A	0.9900

C19—O2—C20	116.62 (17)	C10—C11—H11C	109.5
C8—N1—C1	109.44 (18)	H11A—C11—H11C	109.5
C8—N1—C9	127.0 (2)	H11B—C11—H11C	109.5
C1—N1—C9	123.49 (17)	C8—C12—C13	114.42 (18)
N1—C1—C2	128.7 (2)	C8—C12—H12A	108.7
N1—C1—C6	108.43 (17)	C13—C12—H12A	108.7
C2—C1—C6	122.9 (2)	C8—C12—H12B	108.7
C3—C2—C1	116.8 (2)	C13—C12—H12B	108.7
C3—C2—H2	121.6	H12A—C12—H12B	107.6
C1—C2—H2	121.6	C14—C13—C18	119.03 (18)
C2—C3—C4	121.6 (2)	C14—C13—C12	120.5 (2)
C2—C3—H3	119.2	C18—C13—C12	120.43 (19)
C4—C3—H3	119.2	C13—C14—C15	120.6 (2)
C5—C4—C3	121.4 (2)	C13—C14—H14	119.7
C5—C4—H4	119.3	C15—C14—H14	119.7
C3—C4—H4	119.3	C16—C15—C14	119.9 (2)
C4—C5—C6	118.8 (2)	C16—C15—H15	120.1
C4—C5—H5	120.6	C14—C15—H15	120.1
C6—C5—H5	120.6	C15—C16—C17	119.9 (2)
C5—C6—C1	118.65 (19)	C15—C16—H16	120.1
C5—C6—C7	135.6 (2)	C17—C16—H16	120.1
C1—C6—C7	105.70 (19)	C18—C17—C16	120.0 (2)
C8—C7—C6	107.73 (18)	C18—C17—H17	120.0
C8—C7—C19	124.58 (19)	C16—C17—H17	120.0
C6—C7—C19	127.7 (2)	C17—C18—C13	120.6 (2)
N1—C8—C7	108.7 (2)	C17—C18—H18	119.7
N1—C8—C12	121.3 (2)	C13—C18—H18	119.7
C7—C8—C12	129.92 (19)	O1—C19—O2	121.99 (19)
N1—C9—C10	113.02 (19)	O1—C19—C7	126.6 (2)
N1—C9—H9A	109.0	O2—C19—C7	111.41 (18)
C10—C9—H9A	109.0	O2—C20—C21	106.99 (19)
N1—C9—H9B	109.0	O2—C20—H20A	110.3
C10—C9—H9B	109.0	C21—C20—H20A	110.3
H9A—C9—H9B	107.8	O2—C20—H20B	110.3
C11—C10—C9	110.2 (2)	C21—C20—H20B	110.3
C11—C10—H10A	109.6	H20A—C20—H20B	108.6
C9—C10—H10A	109.6	C20—C21—H21A	109.5
C11—C10—H10B	109.6	C20—C21—H21B	109.5
C9—C10—H10B	109.6	H21A—C21—H21B	109.5
H10A—C10—H10B	108.1	C20—C21—H21C	109.5
C10—C11—H11A	109.5	H21A—C21—H21C	109.5
C10—C11—H11B	109.5	H21B—C21—H21C	109.5
H11A—C11—H11B	109.5

C8—N1—C1—C2	−180.0 (2)	C6—C7—C8—C12	175.6 (2)
C9—N1—C1—C2	−2.4 (3)	C19—C7—C8—C12	−6.3 (4)
C8—N1—C1—C6	0.2 (2)	C8—N1—C9—C10	96.0 (3)
C9—N1—C1—C6	177.74 (19)	C1—N1—C9—C10	−81.1 (2)
N1—C1—C2—C3	−179.6 (2)	N1—C9—C10—C11	−178.64 (18)
C6—C1—C2—C3	0.2 (3)	N1—C8—C12—C13	−75.8 (3)
C1—C2—C3—C4	−0.7 (3)	C7—C8—C12—C13	107.9 (2)
C2—C3—C4—C5	0.6 (4)	C8—C12—C13—C14	127.6 (2)
C3—C4—C5—C6	−0.1 (3)	C8—C12—C13—C18	−55.3 (3)
C4—C5—C6—C1	−0.4 (3)	C18—C13—C14—C15	−0.6 (3)
C4—C5—C6—C7	−179.1 (2)	C12—C13—C14—C15	176.5 (2)
N1—C1—C6—C5	−179.83 (18)	C13—C14—C15—C16	0.0 (3)
C2—C1—C6—C5	0.3 (3)	C14—C15—C16—C17	0.6 (3)
N1—C1—C6—C7	−0.8 (2)	C15—C16—C17—C18	−0.5 (3)
C2—C1—C6—C7	179.4 (2)	C16—C17—C18—C13	−0.1 (3)
C5—C6—C7—C8	179.9 (2)	C14—C13—C18—C17	0.7 (3)
C1—C6—C7—C8	1.1 (2)	C12—C13—C18—C17	−176.49 (19)
C5—C6—C7—C19	1.8 (4)	C20—O2—C19—O1	−0.7 (3)
C1—C6—C7—C19	−177.0 (2)	C20—O2—C19—C7	178.6 (2)
C1—N1—C8—C7	0.5 (2)	C8—C7—C19—O1	−5.9 (4)
C9—N1—C8—C7	−176.92 (19)	C6—C7—C19—O1	171.8 (2)
C1—N1—C8—C12	−176.43 (18)	C8—C7—C19—O2	174.8 (2)
C9—N1—C8—C12	6.1 (3)	C6—C7—C19—O2	−7.5 (3)
C6—C7—C8—N1	−1.0 (2)	C19—O2—C20—C21	−179.8 (2)
C19—C7—C8—N1	177.15 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.95	2.71	3.653 (3)	173
C9—H9B···O1ⁱ	0.99	2.88	3.680 (3)	138
C11—H11A···O1ⁱ	0.98	2.69	3.514 (3)	142
C12—H12A···O1	0.99	2.39	3.044 (3)	123
C18—H18···O1	0.95	2.96	3.620 (3)	128
C21—H21A···O2ⁱⁱ	0.98	2.91	3.555 (3)	124
C3—H3···Cgⁱⁱⁱ	0.95	2.82	3.632 (3)	144

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₃NO₂
M_r	321.40
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	113
a, b, c (Å)	16.231 (3), 19.479 (4), 5.5226 (11)
V (Å³)	1746.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.16 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.985, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	13765, 2204, 2060
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.102, 1.07
No. of reflections	2204
No. of parameters	220
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.15

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.95	2.708	3.653 (3)	173
C9—H9B···O1ⁱ	0.99	2.880	3.680 (3)	138
C11—H11A···O1ⁱ	0.98	2.686	3.514 (3)	142
C12—H12A···O1	0.99	2.386	3.044 (3)	123
C18—H18···O1	0.95	2.961	3.620 (3)	128
C21—H21A···O2ⁱⁱ	0.98	2.912	3.555 (3)	124
C3—H3···Cgⁱⁱⁱ	0.95	2.82	3.632 (3)	144

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

References

Du, Y., Liu, R., Linn, G. & Zhao, K. (2006). Org. Lett. 8, 5919–5922. Web of Science CSD CrossRef PubMed CAS Google Scholar
Jin, H., Li, P., Liu, B. & Cheng, X. (2009). Acta Cryst. E65, o236. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1284

doi:10.1107/S1600536809016493

Open

access