3-Phenyl-2-(pyrrolidin-1-yl)-6,7-dihydro-5H-cyclo­penta­[b]thieno[5,4-d]pyrimidin-4(3H)-one

Hu, Y.-G.; Chen, Y.-L.; Xie, T.; Liu, M.-G.

doi:10.1107/S160053680703365X

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3-Phenyl-2-(pyrrolidin-1-yl)-6,7-dihydro-5H-cyclopenta[b]thieno[5,4-d]pyrimidin-4(3H)-one

Y.-G. Hu, Y.-L. Chen, T. Xie and M.-G. Liu

The title compound, C₁₉H₁₉N₃OS, was synthesized by base catalytic reaction of ethyl 2-(phenyliminomethyleneamino)-5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxylate with pyrrolidine. In the molecule, the fused thienopyrimidinone ring system is essentially planar, making a dihedral angle of 68.64 (9)° with the phenyl ring. The conformations of the cyclopentene and pyrrolidine rings are both distorted half-chair. The crystal packing is mainly stabilized by C—H

O and C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703365X/is2190sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680703365X/is2190Isup2.hkl Contains datablock I

CCDC reference: 657747

checkCIF report

Key indicators

Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.004 Å
R factor = 0.054
wR factor = 0.153
Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.72 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C4
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.07

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Derivatives of pyrimidinone are attracting increasing attention in the synthetic chemistry community because of the important role played by such systems in many natural products, also in antibiotics and drugs (Modica et al., 2004; Panico et al., 2001; Ding et al., 2004). Recently, we have been interested in the synthesis of new thieno[3,2-d]pyrimidone derivatives. Some related X-ray crystal structure reports for pyrimidinone derivatives have been published (Zheng et al., 2006; Xu et al., 2005). Here, the structure of the title compound, which may be used as a new precursor for obtaining bioactive molecules, is reported (Fig. 1). In the molecule, the bond lengths and angles are unexceptional. The fused ring of the thieno[3,2-d]pyrimidone system is essentially planar, making a dihedral angle of 68.64 (9)° with the pnenyl C14—C19 ring. C1—C5 and C10/C11/C12/C13/N3 rings have a total puckering amplitude of 0.118 (4) and 0.418 (3) Å, respectively (Cremer & Pople, 1975) and a distorted half-chair form [φ = 80.0 (2) and 93.2 (3)°]. The crystal packing is mainly stabilized by C—H···O and C—H···π interactions (Table 1 and Fig. 2). There are no π-π interactions.

Related literature top

Many derivatives of pyrimidinone have been prepared and their biological and pharmaceutical activities have been studied by Modica et al. (2004) and Panico et al. (2001). For related literature, see: Cremer & Pople (1975); Ding et al. (2004); Xu et al. (2005); Zheng et al. (2006).

Experimental top

To a solution of ethyl 2-(phenyliminomethyleneamino)-5,6-dihydro-4H- cyclopenta[b]thiophene-2-carboxylate (3 mmol) in anhydrous dichloromethane (15 ml) was added pyrrolidine (3 mmol). After stirring the reaction mixture for 2 h, the solvent was removed and anhydrous ethanol (10 ml) with several drops of EtONa in EtOH was added. The mixture was stirred for 4 h at room temperature. The solution was concentrated under reduced pressure and the residue was recrystallized from ethanol to give the title compound in a yield of 86%. Single crystals suitable for X-ray diffraction were obtained by recrystallization from a mixed solvent of ethanol and dichloromethane (1:1 v/v) at room temperature.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. The packing diagram viewed along the b axis, showing the C—H···O hydrogen bonds as dashed lines.

3-Phenyl-2-(pyrrolidin-1-yl)-6,7-dihydro- 5H-cyclopenta[b]thieno[5,4-d]pyrimidin-4(3H)-one top

Crystal data top

C₁₉H₁₉N₃OS	F(000) = 1424
M_r = 337.43	D_x = 1.315 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3147 reflections
a = 23.094 (3) Å	θ = 2.4–25.8°
b = 8.5709 (10) Å	µ = 0.20 mm⁻¹
c = 17.271 (2) Å	T = 299 K
β = 94.503 (2)°	Plate, colourless
V = 3408.1 (7) Å³	0.30 × 0.20 × 0.06 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	2613 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
Graphite monochromator	θ_max = 26.0°, θ_min = 1.8°
φ and ω scans	h = −27→28
12733 measured reflections	k = −10→10
3323 independent reflections	l = −21→21

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + 2.2147P] where P = (F_o² + 2F_c²)/3
3323 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₉H₁₉N₃OS	V = 3408.1 (7) Å³
M_r = 337.43	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 23.094 (3) Å	µ = 0.20 mm⁻¹
b = 8.5709 (10) Å	T = 299 K
c = 17.271 (2) Å	0.30 × 0.20 × 0.06 mm
β = 94.503 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2613 reflections with I > 2σ(I)
12733 measured reflections	R_int = 0.044
3323 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.05	Δρ_max = 0.23 e Å⁻³
3323 reflections	Δρ_min = −0.29 e Å⁻³
217 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
C1	0.39367 (11)	−0.0658 (3)	0.13067 (14)	0.0543 (6)
C2	0.41197 (13)	−0.2289 (4)	0.15237 (19)	0.0809 (9)
H2A	0.3879	−0.3051	0.1235	0.097*
H2B	0.4099	−0.2471	0.2075	0.097*
C3	0.47452 (15)	−0.2359 (5)	0.1303 (2)	0.1023 (12)
H3A	0.4770	−0.3026	0.0853	0.123*
H3B	0.4994	−0.2790	0.1729	0.123*
C4	0.49430 (14)	−0.0708 (5)	0.1119 (2)	0.1030 (13)
H4A	0.5214	−0.0306	0.1528	0.124*
H4B	0.5121	−0.0673	0.0629	0.124*
C5	0.43829 (11)	0.0173 (3)	0.10746 (16)	0.0630 (7)
C6	0.34115 (9)	0.0224 (2)	0.12941 (13)	0.0442 (5)
C7	0.34809 (9)	0.1721 (3)	0.10331 (13)	0.0442 (5)
C8	0.28480 (9)	−0.0255 (2)	0.14761 (13)	0.0420 (5)
C9	0.25506 (9)	0.2454 (2)	0.11414 (12)	0.0380 (5)
C10	0.16339 (9)	0.3712 (2)	0.15540 (14)	0.0477 (6)
H10A	0.1720	0.3276	0.2068	0.057*
H10B	0.1291	0.3206	0.1309	0.057*
C11	0.15533 (11)	0.5480 (2)	0.15893 (16)	0.0573 (7)
H11A	0.1152	0.5750	0.1656	0.069*
H11B	0.1801	0.5934	0.2010	0.069*
C12	0.17302 (11)	0.6016 (2)	0.08106 (16)	0.0559 (6)
H12A	0.1814	0.7125	0.0813	0.067*
H12B	0.1431	0.5791	0.0400	0.067*
C13	0.22717 (10)	0.5061 (2)	0.07185 (14)	0.0498 (6)
H13A	0.2340	0.4931	0.0175	0.060*
H13B	0.2610	0.5541	0.0988	0.060*
C14	0.18283 (9)	0.0414 (2)	0.14200 (13)	0.0399 (5)
C15	0.16433 (11)	−0.0078 (3)	0.21238 (15)	0.0542 (6)
H15	0.1890	−0.0014	0.2575	0.065*
C16	0.10902 (13)	−0.0664 (3)	0.2147 (2)	0.0689 (8)
H16	0.0962	−0.0998	0.2616	0.083*
C17	0.07258 (12)	−0.0756 (3)	0.1479 (2)	0.0726 (9)
H17	0.0353	−0.1159	0.1496	0.087*
C18	0.09132 (11)	−0.0254 (3)	0.07868 (19)	0.0634 (7)
H18	0.0663	−0.0298	0.0338	0.076*
C19	0.14687 (10)	0.0317 (2)	0.07496 (15)	0.0482 (6)
H19	0.1598	0.0632	0.0277	0.058*
N1	0.24184 (7)	0.09507 (17)	0.13812 (10)	0.0381 (4)
N2	0.30734 (8)	0.28498 (19)	0.09507 (11)	0.0443 (4)
N3	0.21341 (7)	0.35543 (18)	0.10766 (10)	0.0402 (4)
O1	0.27071 (7)	−0.15575 (17)	0.16791 (11)	0.0606 (5)
S1	0.41935 (3)	0.20650 (8)	0.08088 (5)	0.0691 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0435 (14)	0.0687 (14)	0.0502 (14)	0.0220 (11)	0.0003 (11)	−0.0011 (11)
C2	0.0651 (19)	0.0815 (19)	0.097 (2)	0.0427 (16)	0.0127 (17)	0.0180 (16)
C3	0.071 (2)	0.114 (3)	0.123 (3)	0.055 (2)	0.015 (2)	0.006 (2)
C4	0.055 (2)	0.137 (3)	0.121 (3)	0.048 (2)	0.027 (2)	0.028 (2)
C5	0.0397 (14)	0.0848 (18)	0.0645 (17)	0.0224 (13)	0.0047 (12)	0.0015 (13)
C6	0.0369 (12)	0.0485 (11)	0.0468 (13)	0.0123 (9)	0.0009 (9)	−0.0022 (9)
C7	0.0336 (11)	0.0512 (11)	0.0479 (13)	0.0046 (9)	0.0026 (9)	−0.0035 (10)
C8	0.0382 (12)	0.0386 (10)	0.0480 (13)	0.0091 (8)	−0.0043 (9)	−0.0017 (9)
C9	0.0387 (12)	0.0329 (9)	0.0421 (12)	0.0034 (8)	0.0010 (9)	−0.0054 (8)
C10	0.0371 (12)	0.0395 (10)	0.0671 (15)	0.0074 (9)	0.0089 (11)	−0.0094 (10)
C11	0.0547 (15)	0.0385 (11)	0.0794 (18)	0.0105 (10)	0.0107 (13)	−0.0122 (11)
C12	0.0560 (15)	0.0366 (11)	0.0728 (17)	0.0117 (10)	−0.0089 (12)	−0.0043 (10)
C13	0.0568 (15)	0.0346 (10)	0.0576 (15)	0.0055 (9)	0.0028 (11)	0.0014 (9)
C14	0.0336 (11)	0.0279 (9)	0.0584 (13)	0.0053 (8)	0.0048 (10)	−0.0011 (8)
C15	0.0542 (15)	0.0460 (12)	0.0632 (16)	0.0041 (10)	0.0101 (12)	0.0042 (11)
C16	0.0641 (18)	0.0481 (13)	0.099 (2)	0.0045 (12)	0.0351 (18)	0.0120 (13)
C17	0.0427 (15)	0.0408 (12)	0.136 (3)	−0.0017 (10)	0.0174 (18)	0.0003 (15)
C18	0.0404 (14)	0.0461 (12)	0.101 (2)	0.0009 (10)	−0.0098 (14)	−0.0076 (13)
C19	0.0428 (13)	0.0361 (10)	0.0653 (15)	0.0062 (9)	0.0009 (11)	−0.0031 (10)
N1	0.0322 (9)	0.0332 (8)	0.0486 (10)	0.0055 (7)	0.0018 (8)	−0.0009 (7)
N2	0.0362 (10)	0.0399 (9)	0.0573 (12)	0.0035 (7)	0.0064 (8)	−0.0003 (8)
N3	0.0376 (10)	0.0333 (8)	0.0498 (10)	0.0060 (7)	0.0038 (8)	−0.0018 (7)
O1	0.0515 (10)	0.0365 (8)	0.0931 (14)	0.0106 (7)	−0.0001 (9)	0.0087 (8)
S1	0.0379 (4)	0.0785 (5)	0.0927 (6)	0.0067 (3)	0.0174 (4)	0.0095 (4)

Geometric parameters (Å, º) top

C1—C5	1.340 (4)	C10—H10A	0.9700
C1—C6	1.428 (3)	C10—H10B	0.9700
C1—C2	1.499 (3)	C11—C12	1.507 (4)
C2—C3	1.524 (4)	C11—H11A	0.9700
C2—H2A	0.9700	C11—H11B	0.9700
C2—H2B	0.9700	C12—C13	1.514 (3)
C3—C4	1.528 (5)	C12—H12A	0.9700
C3—H3A	0.9700	C12—H12B	0.9700
C3—H3B	0.9700	C13—N3	1.477 (3)
C4—C5	1.495 (3)	C13—H13A	0.9700
C4—H4A	0.9700	C13—H13B	0.9700
C4—H4B	0.9700	C14—C19	1.373 (3)
C5—S1	1.732 (3)	C14—C15	1.385 (3)
C6—C7	1.373 (3)	C14—N1	1.445 (3)
C6—C8	1.423 (3)	C15—C16	1.376 (4)
C7—N2	1.350 (3)	C15—H15	0.9300
C7—S1	1.745 (2)	C16—C17	1.376 (4)
C8—O1	1.222 (3)	C16—H16	0.9300
C8—N1	1.433 (2)	C17—C18	1.372 (4)
C9—N2	1.321 (3)	C17—H17	0.9300
C9—N3	1.345 (2)	C18—C19	1.379 (3)
C9—N1	1.395 (2)	C18—H18	0.9300
C10—N3	1.477 (3)	C19—H19	0.9300
C10—C11	1.528 (3)

C5—C1—C6	112.7 (2)	C12—C11—H11A	111.2
C5—C1—C2	111.2 (2)	C10—C11—H11A	111.2
C6—C1—C2	136.0 (2)	C12—C11—H11B	111.2
C1—C2—C3	103.2 (3)	C10—C11—H11B	111.2
C1—C2—H2A	111.1	H11A—C11—H11B	109.1
C3—C2—H2A	111.1	C11—C12—C13	102.31 (18)
C1—C2—H2B	111.1	C11—C12—H12A	111.3
C3—C2—H2B	111.1	C13—C12—H12A	111.3
H2A—C2—H2B	109.1	C11—C12—H12B	111.3
C2—C3—C4	108.7 (2)	C13—C12—H12B	111.3
C2—C3—H3A	110.0	H12A—C12—H12B	109.2
C4—C3—H3A	110.0	N3—C13—C12	102.83 (18)
C2—C3—H3B	110.0	N3—C13—H13A	111.2
C4—C3—H3B	110.0	C12—C13—H13A	111.2
H3A—C3—H3B	108.3	N3—C13—H13B	111.2
C5—C4—C3	102.0 (3)	C12—C13—H13B	111.2
C5—C4—H4A	111.4	H13A—C13—H13B	109.1
C3—C4—H4A	111.4	C19—C14—C15	120.9 (2)
C5—C4—H4B	111.4	C19—C14—N1	119.35 (19)
C3—C4—H4B	111.4	C15—C14—N1	119.6 (2)
H4A—C4—H4B	109.2	C16—C15—C14	119.2 (3)
C1—C5—C4	113.5 (3)	C16—C15—H15	120.4
C1—C5—S1	113.14 (18)	C14—C15—H15	120.4
C4—C5—S1	133.3 (2)	C15—C16—C17	120.3 (3)
C7—C6—C8	118.32 (18)	C15—C16—H16	119.8
C7—C6—C1	112.3 (2)	C17—C16—H16	119.8
C8—C6—C1	129.4 (2)	C18—C17—C16	119.9 (2)
N2—C7—C6	127.3 (2)	C18—C17—H17	120.1
N2—C7—S1	121.15 (17)	C16—C17—H17	120.1
C6—C7—S1	111.55 (16)	C17—C18—C19	120.7 (3)
O1—C8—C6	126.57 (19)	C17—C18—H18	119.7
O1—C8—N1	119.61 (19)	C19—C18—H18	119.7
C6—C8—N1	113.80 (17)	C14—C19—C18	119.0 (2)
N2—C9—N3	117.44 (18)	C14—C19—H19	120.5
N2—C9—N1	122.49 (17)	C18—C19—H19	120.5
N3—C9—N1	120.04 (18)	C9—N1—C8	122.32 (17)
N3—C10—C11	102.49 (17)	C9—N1—C14	122.50 (16)
N3—C10—H10A	111.3	C8—N1—C14	114.33 (15)
C11—C10—H10A	111.3	C9—N2—C7	115.67 (18)
N3—C10—H10B	111.3	C9—N3—C13	118.14 (17)
C11—C10—H10B	111.3	C9—N3—C10	127.09 (18)
H10A—C10—H10B	109.2	C13—N3—C10	110.91 (15)
C12—C11—C10	102.94 (18)	C5—S1—C7	90.33 (11)

C5—C1—C2—C3	−5.6 (3)	N1—C14—C19—C18	177.51 (18)
C6—C1—C2—C3	175.2 (3)	C17—C18—C19—C14	−1.7 (3)
C1—C2—C3—C4	10.9 (4)	N2—C9—N1—C8	3.2 (3)
C2—C3—C4—C5	−11.9 (4)	N3—C9—N1—C8	−178.62 (18)
C6—C1—C5—C4	177.3 (3)	N2—C9—N1—C14	−165.56 (19)
C2—C1—C5—C4	−2.1 (4)	N3—C9—N1—C14	12.6 (3)
C6—C1—C5—S1	−1.1 (3)	O1—C8—N1—C9	−179.2 (2)
C2—C1—C5—S1	179.5 (2)	C6—C8—N1—C9	−0.8 (3)
C3—C4—C5—C1	8.7 (4)	O1—C8—N1—C14	−9.5 (3)
C3—C4—C5—S1	−173.2 (3)	C6—C8—N1—C14	168.88 (18)
C5—C1—C6—C7	1.1 (3)	C19—C14—N1—C9	63.7 (2)
C2—C1—C6—C7	−179.7 (3)	C15—C14—N1—C9	−119.9 (2)
C5—C1—C6—C8	178.0 (2)	C19—C14—N1—C8	−106.0 (2)
C2—C1—C6—C8	−2.8 (5)	C15—C14—N1—C8	70.4 (2)
C8—C6—C7—N2	2.7 (4)	N3—C9—N2—C7	179.18 (19)
C1—C6—C7—N2	180.0 (2)	N1—C9—N2—C7	−2.6 (3)
C8—C6—C7—S1	−177.87 (16)	C6—C7—N2—C9	−0.3 (3)
C1—C6—C7—S1	−0.5 (3)	S1—C7—N2—C9	−179.74 (15)
C7—C6—C8—O1	176.4 (2)	N2—C9—N3—C13	6.6 (3)
C1—C6—C8—O1	−0.4 (4)	N1—C9—N3—C13	−171.66 (18)
C7—C6—C8—N1	−1.9 (3)	N2—C9—N3—C10	−149.2 (2)
C1—C6—C8—N1	−178.7 (2)	N1—C9—N3—C10	32.6 (3)
N3—C10—C11—C12	33.1 (2)	C12—C13—N3—C9	−175.30 (18)
C10—C11—C12—C13	−43.4 (2)	C12—C13—N3—C10	−15.8 (2)
C11—C12—C13—N3	36.1 (2)	C11—C10—N3—C9	146.5 (2)
C19—C14—C15—C16	−0.3 (3)	C11—C10—N3—C13	−10.7 (2)
N1—C14—C15—C16	−176.64 (19)	C1—C5—S1—C7	0.7 (2)
C14—C15—C16—C17	−0.1 (3)	C4—C5—S1—C7	−177.4 (3)
C15—C16—C17—C18	−0.4 (4)	N2—C7—S1—C5	179.4 (2)
C16—C17—C18—C19	1.3 (4)	C6—C7—S1—C5	−0.06 (19)
C15—C14—C19—C18	1.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O1ⁱ	0.97	2.45	3.309 (3)	148
C10—H10B···Cg5	0.97	2.90	3.429 (2)	115
C12—H12A···Cg5ⁱⁱ	0.97	2.89	3.630 (2)	134
C12—H12B···Cg1ⁱⁱⁱ	0.97	2.93	3.790 (3)	148
C13—H13A···Cg4ⁱⁱⁱ	0.97	2.67	3.542 (3)	150

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉N₃OS
M_r	337.43
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	299
a, b, c (Å)	23.094 (3), 8.5709 (10), 17.271 (2)
β (°)	94.503 (2)
V (Å³)	3408.1 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.20 × 0.06

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12733, 3323, 2613
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.153, 1.05
No. of reflections	3323
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.29

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 2001), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O1ⁱ	0.97	2.45	3.309 (3)	148
C10—H10B···Cg5	0.97	2.90	3.429 (2)	115
C12—H12A···Cg5ⁱⁱ	0.97	2.89	3.630 (2)	134
C12—H12B···Cg1ⁱⁱⁱ	0.97	2.93	3.790 (3)	148
C13—H13A···Cg4ⁱⁱⁱ	0.97	2.67	3.542 (3)	150

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

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