6-Ethyl-2-(piperidin-1-yl)-3-p-tolyl­thieno[2,3-d]pyrimidin-4(3H)-one

Xie, H.; Peng, X.; Hu, Y.

doi:10.1107/S1600536807057145

6-Ethyl-2-(piperidin-1-yl)-3-p-tolylthieno[2,3-d]pyrimidin-4(3H)-one

H. Xie, X. Peng and Y. Hu

The crystal structure of the title compound, C₂₀H₂₃N₃OS, is stabilized by intermolecular C—H

O hydrogen bonds. The molecule contains a planar heterocyclic ring system, which forms a dihedral angle of 65.87 (1)° with the adjacent tolyl ring. The piperidinyl ring has a distored chair conformation.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807057145/bt2600sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807057145/bt2600Isup2.hkl Contains datablock I

CCDC reference: 672931

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R factor = 0.069
wR factor = 0.168
Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.78 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.09 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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

The derivatives of heterocycles containing the thienopyrimidine system, which are well known bioisosteres of quinazolines, are of great importance because of their remarkable biological properties (Walter, 1999a; Walter, 1999b; Ding et al., 2004). Recently, we have focused on the synthesis of fused heterocyclic systems containing thienopyrimidine via aza-Wittig reaction at room temperature. Some X-ray crystal structures of fused pyrimidinone derivatives have been reported (Hu et al., 2006; Hu et al., 2007). The title compound (Fig. 1) may be used as a new precursor for obtaining bioactive molecules. In the molecule, the bond lengths and angles are unexceptional. The thienopyrimidine ring system is almost planar, with a maximum deviation of 0.046 Å for atom N3. The tolyl ring is twisted with respect to it [dihedral angle 65.87 (1)°]. The piperidinyl ring in shows a distored chair conformation [ϕ =187 (9)° and θ = 180.0 (3)°, puckering amplitude = 0.571 (3) Å]. Intermolecular C—H···O hydrogen bonds (Fig. 2 and Table 2) are effective in stabilizing the crystal structure.

Related literature top

For preparation and biological activity, see: Walter (1999a,b). For related literature, see: Ding et al. (2004); Hu et al. (2006, 2007).

Experimental top

To a solution of the ethyl 2-((p-tolylimino)methyleneamino)-5-ethylthiophene-3-carboxylate(II) (3 mmol) in dichloromethane (5 ml) was added piperidine(3 mmol). After stirring the reaction mixture for 1 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%. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from a mixed solvent of ethanol and dichloromethane (1:1 v/v) at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 200; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labeling scheme.
	Fig. 2. The packing in the crystal structure, showing the C—H···O hydrogen bonds as dashed lines.

6-Ethyl-2-(piperidin-1-yl)-3-p-tolylthieno[2,3-d]pyrimidin-4(3H)-one top

Crystal data top

C₂₀H₂₃N₃OS	F(000) = 752
M_r = 353.47	D_x = 1.244 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2891 reflections
a = 6.5376 (4) Å	θ = 2.6–22.9°
b = 18.6415 (12) Å	µ = 0.18 mm⁻¹
c = 15.5507 (10) Å	T = 296 K
β = 94.967 (1)°	Block, colorless
V = 1888.1 (2) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	3683 independent reflections
Radiation source: fine-focus sealed tube	2714 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −8→8
T_min = 0.947, T_max = 0.964	k = −22→22
16199 measured reflections	l = −18→19

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.168	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.072P)² + 0.7436P] where P = (F_o² + 2F_c²)/3
3683 reflections	(Δ/σ)_max < 0.001
228 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₀H₂₃N₃OS	V = 1888.1 (2) Å³
M_r = 353.47	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.5376 (4) Å	µ = 0.18 mm⁻¹
b = 18.6415 (12) Å	T = 296 K
c = 15.5507 (10) Å	0.30 × 0.20 × 0.20 mm
β = 94.967 (1)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	3683 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2714 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.964	R_int = 0.042
16199 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.168	H-atom parameters constrained
S = 1.09	Δρ_max = 0.33 e Å⁻³
3683 reflections	Δρ_min = −0.18 e Å⁻³
228 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	0.6795 (5)	0.80842 (15)	0.33985 (18)	0.0534 (7)
H1A	0.7609	0.8283	0.3893	0.064*
H1B	0.7646	0.7747	0.3116	0.064*
C2	0.4956 (5)	0.76995 (16)	0.3697 (2)	0.0663 (9)
H2A	0.5412	0.7332	0.4112	0.080*
H2B	0.4209	0.7466	0.3208	0.080*
C3	0.3549 (5)	0.82198 (17)	0.4107 (2)	0.0698 (9)
H3A	0.4230	0.8405	0.4640	0.084*
H3B	0.2311	0.7973	0.4244	0.084*
C4	0.2989 (5)	0.88368 (17)	0.3490 (2)	0.0667 (9)
H4A	0.2149	0.8656	0.2992	0.080*
H4B	0.2186	0.9187	0.3776	0.080*
C5	0.4870 (5)	0.91967 (14)	0.3192 (2)	0.0578 (8)
H5A	0.4461	0.9570	0.2778	0.069*
H5B	0.5654	0.9417	0.3681	0.069*
C6	0.7593 (4)	0.89267 (13)	0.22814 (16)	0.0416 (6)
C7	0.9598 (4)	0.97979 (14)	0.18017 (17)	0.0474 (7)
C8	1.0504 (4)	0.93702 (14)	0.12372 (17)	0.0456 (6)
C9	0.9877 (4)	0.86358 (14)	0.11460 (16)	0.0438 (6)
C10	0.7312 (4)	0.77628 (13)	0.15011 (16)	0.0419 (6)
C11	0.8398 (5)	0.71284 (14)	0.16331 (18)	0.0539 (7)
H11	0.9759	0.7135	0.1863	0.065*
C12	0.7433 (6)	0.64854 (15)	0.14186 (19)	0.0632 (9)
H12	0.8157	0.6059	0.1513	0.076*
C13	0.5423 (6)	0.64604 (15)	0.10678 (18)	0.0607 (9)
C14	0.4362 (5)	0.70978 (15)	0.09467 (18)	0.0551 (7)
H14	0.2997	0.7090	0.0722	0.066*
C15	0.5298 (4)	0.77485 (14)	0.11540 (17)	0.0468 (7)
H15	0.4572	0.8174	0.1060	0.056*
C16	0.4395 (8)	0.57519 (17)	0.0815 (3)	0.0977 (14)
H16A	0.3044	0.5742	0.1013	0.147*
H16B	0.5194	0.5364	0.1075	0.147*
H16C	0.4297	0.5701	0.0199	0.147*
C17	1.1956 (5)	0.97442 (16)	0.07732 (19)	0.0571 (8)
H17	1.2713	0.9526	0.0366	0.068*
C18	1.2124 (5)	1.04385 (16)	0.09795 (19)	0.0572 (8)
C19	1.3451 (5)	1.10055 (18)	0.0615 (2)	0.0711 (9)
H19A	1.4076	1.0805	0.0125	0.085*
H19B	1.2584	1.1402	0.0405	0.085*
C20	1.5056 (7)	1.1280 (3)	0.1226 (3)	0.1155 (16)
H20A	1.4451	1.1510	0.1694	0.173*
H20B	1.5872	1.1621	0.0943	0.173*
H20C	1.5911	1.0891	0.1445	0.173*
N1	0.6137 (3)	0.86650 (10)	0.27945 (13)	0.0433 (5)
N2	0.8165 (4)	0.95937 (11)	0.23473 (14)	0.0489 (6)
N3	0.8313 (3)	0.84460 (10)	0.16904 (13)	0.0412 (5)
O1	1.0499 (3)	0.82006 (10)	0.06466 (13)	0.0585 (5)
S1	1.05291 (14)	1.06658 (4)	0.17733 (6)	0.0656 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0629 (19)	0.0562 (17)	0.0420 (15)	0.0139 (14)	0.0093 (14)	0.0072 (13)
C2	0.090 (2)	0.0512 (17)	0.0617 (19)	0.0066 (16)	0.0285 (18)	0.0191 (14)
C3	0.074 (2)	0.076 (2)	0.065 (2)	0.0014 (17)	0.0359 (18)	0.0127 (16)
C4	0.064 (2)	0.0637 (19)	0.077 (2)	0.0125 (16)	0.0345 (17)	0.0083 (16)
C5	0.069 (2)	0.0400 (15)	0.069 (2)	0.0081 (13)	0.0288 (16)	−0.0006 (13)
C6	0.0447 (15)	0.0396 (14)	0.0414 (14)	0.0035 (11)	0.0091 (12)	0.0025 (11)
C7	0.0486 (17)	0.0454 (15)	0.0491 (16)	−0.0027 (12)	0.0098 (13)	0.0015 (12)
C8	0.0426 (16)	0.0502 (15)	0.0448 (15)	−0.0008 (12)	0.0087 (13)	0.0002 (12)
C9	0.0403 (15)	0.0491 (15)	0.0422 (14)	0.0042 (12)	0.0048 (12)	−0.0008 (12)
C10	0.0521 (17)	0.0357 (13)	0.0393 (14)	0.0015 (11)	0.0127 (12)	−0.0002 (10)
C11	0.066 (2)	0.0466 (16)	0.0494 (16)	0.0115 (14)	0.0086 (14)	0.0011 (12)
C12	0.098 (3)	0.0391 (16)	0.0536 (18)	0.0144 (16)	0.0148 (18)	0.0015 (13)
C13	0.098 (3)	0.0426 (16)	0.0426 (16)	−0.0129 (16)	0.0137 (17)	−0.0034 (12)
C14	0.062 (2)	0.0535 (17)	0.0499 (17)	−0.0109 (14)	0.0076 (14)	−0.0033 (13)
C15	0.0536 (18)	0.0393 (14)	0.0487 (16)	0.0024 (12)	0.0108 (13)	0.0020 (11)
C16	0.157 (4)	0.052 (2)	0.082 (3)	−0.024 (2)	−0.001 (3)	−0.0102 (18)
C17	0.0532 (19)	0.0645 (19)	0.0559 (18)	−0.0077 (14)	0.0190 (15)	−0.0054 (14)
C18	0.0542 (19)	0.0625 (18)	0.0564 (18)	−0.0115 (14)	0.0141 (15)	0.0009 (14)
C19	0.064 (2)	0.075 (2)	0.076 (2)	−0.0196 (17)	0.0196 (18)	0.0002 (18)
C20	0.092 (3)	0.134 (4)	0.118 (3)	−0.052 (3)	−0.009 (3)	0.006 (3)
N1	0.0529 (14)	0.0338 (11)	0.0455 (12)	0.0061 (9)	0.0179 (10)	0.0031 (9)
N2	0.0575 (15)	0.0391 (12)	0.0526 (13)	−0.0017 (10)	0.0191 (11)	−0.0034 (10)
N3	0.0429 (13)	0.0393 (11)	0.0425 (12)	0.0025 (9)	0.0097 (10)	−0.0003 (9)
O1	0.0608 (13)	0.0567 (12)	0.0613 (12)	0.0000 (10)	0.0251 (10)	−0.0141 (10)
S1	0.0775 (6)	0.0468 (4)	0.0768 (6)	−0.0131 (4)	0.0311 (5)	−0.0058 (4)

Geometric parameters (Å, º) top

C1—N1	1.473 (3)	C10—C15	1.379 (4)
C1—C2	1.507 (4)	C10—C11	1.385 (4)
C1—H1A	0.9700	C10—N3	1.450 (3)
C1—H1B	0.9700	C11—C12	1.382 (4)
C2—C3	1.516 (4)	C11—H11	0.9300
C2—H2A	0.9700	C12—C13	1.379 (5)
C2—H2B	0.9700	C12—H12	0.9300
C3—C4	1.522 (4)	C13—C14	1.380 (4)
C3—H3A	0.9700	C13—C16	1.518 (4)
C3—H3B	0.9700	C14—C15	1.384 (4)
C4—C5	1.508 (4)	C14—H14	0.9300
C4—H4A	0.9700	C15—H15	0.9300
C4—H4B	0.9700	C16—H16A	0.9600
C5—N1	1.463 (3)	C16—H16B	0.9600
C5—H5A	0.9700	C16—H16C	0.9600
C5—H5B	0.9700	C17—C18	1.336 (4)
C6—N2	1.300 (3)	C17—H17	0.9300
C6—N1	1.383 (3)	C18—C19	1.509 (4)
C6—N3	1.394 (3)	C18—S1	1.736 (3)
C7—C8	1.359 (4)	C19—C20	1.447 (5)
C7—N2	1.371 (3)	C19—H19A	0.9700
C7—S1	1.731 (3)	C19—H19B	0.9700
C8—C17	1.424 (4)	C20—H20A	0.9600
C8—C9	1.433 (4)	C20—H20B	0.9600
C9—O1	1.217 (3)	C20—H20C	0.9600
C9—N3	1.427 (3)

N1—C1—C2	110.4 (2)	C12—C11—H11	120.4
N1—C1—H1A	109.6	C10—C11—H11	120.4
C2—C1—H1A	109.6	C13—C12—C11	121.6 (3)
N1—C1—H1B	109.6	C13—C12—H12	119.2
C2—C1—H1B	109.6	C11—C12—H12	119.2
H1A—C1—H1B	108.1	C12—C13—C14	118.4 (3)
C1—C2—C3	110.8 (3)	C12—C13—C16	121.1 (3)
C1—C2—H2A	109.5	C14—C13—C16	120.5 (4)
C3—C2—H2A	109.5	C13—C14—C15	121.1 (3)
C1—C2—H2B	109.5	C13—C14—H14	119.5
C3—C2—H2B	109.5	C15—C14—H14	119.5
H2A—C2—H2B	108.1	C10—C15—C14	119.7 (3)
C2—C3—C4	109.8 (2)	C10—C15—H15	120.1
C2—C3—H3A	109.7	C14—C15—H15	120.1
C4—C3—H3A	109.7	C13—C16—H16A	109.5
C2—C3—H3B	109.7	C13—C16—H16B	109.5
C4—C3—H3B	109.7	H16A—C16—H16B	109.5
H3A—C3—H3B	108.2	C13—C16—H16C	109.5
C5—C4—C3	111.8 (3)	H16A—C16—H16C	109.5
C5—C4—H4A	109.2	H16B—C16—H16C	109.5
C3—C4—H4A	109.2	C18—C17—C8	113.4 (3)
C5—C4—H4B	109.2	C18—C17—H17	123.3
C3—C4—H4B	109.2	C8—C17—H17	123.3
H4A—C4—H4B	107.9	C17—C18—C19	128.8 (3)
N1—C5—C4	109.6 (2)	C17—C18—S1	111.4 (2)
N1—C5—H5A	109.8	C19—C18—S1	119.8 (2)
C4—C5—H5A	109.8	C20—C19—C18	114.1 (3)
N1—C5—H5B	109.8	C20—C19—H19A	108.7
C4—C5—H5B	109.8	C18—C19—H19A	108.7
H5A—C5—H5B	108.2	C20—C19—H19B	108.7
N2—C6—N1	120.0 (2)	C18—C19—H19B	108.7
N2—C6—N3	123.7 (2)	H19A—C19—H19B	107.6
N1—C6—N3	116.2 (2)	C19—C20—H20A	109.5
C8—C7—N2	126.6 (2)	C19—C20—H20B	109.5
C8—C7—S1	111.0 (2)	H20A—C20—H20B	109.5
N2—C7—S1	122.4 (2)	C19—C20—H20C	109.5
C7—C8—C17	112.8 (2)	H20A—C20—H20C	109.5
C7—C8—C9	119.2 (2)	H20B—C20—H20C	109.5
C17—C8—C9	128.0 (2)	C6—N1—C5	116.6 (2)
O1—C9—N3	120.6 (2)	C6—N1—C1	116.7 (2)
O1—C9—C8	126.3 (2)	C5—N1—C1	111.9 (2)
N3—C9—C8	113.1 (2)	C6—N2—C7	115.1 (2)
C15—C10—C11	120.1 (2)	C6—N3—C9	122.1 (2)
C15—C10—N3	119.7 (2)	C6—N3—C10	121.7 (2)
C11—C10—N3	120.2 (3)	C9—N3—C10	115.55 (19)
C12—C11—C10	119.2 (3)	C7—S1—C18	91.39 (14)

N1—C1—C2—C3	−56.8 (3)	N2—C6—N1—C5	18.2 (4)
C1—C2—C3—C4	53.8 (4)	N3—C6—N1—C5	−159.7 (2)
C2—C3—C4—C5	−54.1 (4)	N2—C6—N1—C1	−117.9 (3)
C3—C4—C5—N1	56.4 (4)	N3—C6—N1—C1	64.3 (3)
N2—C7—C8—C17	−179.0 (3)	C4—C5—N1—C6	162.7 (2)
S1—C7—C8—C17	−0.3 (3)	C4—C5—N1—C1	−59.3 (3)
N2—C7—C8—C9	3.5 (4)	C2—C1—N1—C6	−161.9 (2)
S1—C7—C8—C9	−177.8 (2)	C2—C1—N1—C5	60.0 (3)
C7—C8—C9—O1	177.2 (3)	N1—C6—N2—C7	−179.3 (2)
C17—C8—C9—O1	0.1 (5)	N3—C6—N2—C7	−1.6 (4)
C7—C8—C9—N3	−0.2 (4)	C8—C7—N2—C6	−2.6 (4)
C17—C8—C9—N3	−177.3 (3)	S1—C7—N2—C6	178.8 (2)
C15—C10—C11—C12	−0.4 (4)	N2—C6—N3—C9	4.9 (4)
N3—C10—C11—C12	−177.6 (2)	N1—C6—N3—C9	−177.4 (2)
C10—C11—C12—C13	0.7 (4)	N2—C6—N3—C10	−165.7 (2)
C11—C12—C13—C14	−1.1 (4)	N1—C6—N3—C10	12.0 (3)
C11—C12—C13—C16	178.6 (3)	O1—C9—N3—C6	178.8 (2)
C12—C13—C14—C15	1.3 (4)	C8—C9—N3—C6	−3.7 (3)
C16—C13—C14—C15	−178.4 (3)	O1—C9—N3—C10	−10.1 (3)
C11—C10—C15—C14	0.7 (4)	C8—C9—N3—C10	167.5 (2)
N3—C10—C15—C14	177.9 (2)	C15—C10—N3—C6	61.3 (3)
C13—C14—C15—C10	−1.1 (4)	C11—C10—N3—C6	−121.5 (3)
C7—C8—C17—C18	−0.5 (4)	C15—C10—N3—C9	−110.0 (3)
C9—C8—C17—C18	176.7 (3)	C11—C10—N3—C9	67.3 (3)
C8—C17—C18—C19	−178.5 (3)	C8—C7—S1—C18	0.7 (2)
C8—C17—C18—S1	1.1 (4)	N2—C7—S1—C18	179.5 (2)
C17—C18—C19—C20	−113.6 (4)	C17—C18—S1—C7	−1.0 (3)
S1—C18—C19—C20	67.0 (4)	C19—C18—S1—C7	178.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1ⁱ	0.97	2.58	3.456 (4)	150
C19—H19B···O1ⁱⁱ	0.97	2.59	3.439 (4)	146

Symmetry codes: (i) x−1/2, −y+3/2, z+1/2; (ii) −x+2, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₃N₃OS
M_r	353.47
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	6.5376 (4), 18.6415 (12), 15.5507 (10)
β (°)	94.967 (1)
V (Å³)	1888.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.947, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	16199, 3683, 2714
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.168, 1.09
No. of reflections	3683
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.18

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SAINT-Plus (Bruker, 200, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2001).