2-(Morpholin-4-ylmeth­yl)isoindole-1,3-dione

Sakthivel, P.; Joseph, P.S.; Sebastiyan, A.; Ramesh, M.; Suvaikin, M.Y.

doi:10.1107/S1600536807048738

2-(Morpholin-4-ylmethyl)isoindole-1,3-dione

P. Sakthivel, P. S. Joseph, A. Sebastiyan, M. Ramesh and M. Y. Suvaikin

In the title compound, C₁₃H₁₄N₂O₃, the morpholine ring adopts the usual chair conformation. The crystal structure is stabilized by weak C—H

O hydrogen-bond interactions.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048738/bt2525sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048738/bt2525Isup2.hkl Contains datablock I

CCDC reference: 667329

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.044
wR factor = 0.145
Data-to-parameter ratio = 21.9

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) ...       2.60 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C4      ..       5.84 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.17

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   3 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

Morpholine is used as an important chemical intermediate in the preparation of pesticides. Drugs containing the morpholine ring have established activities that include the reduction of blood sugar and lipid levels (Yoshioka, 1995), and amelioration of obesity and insulin resistance (Fisher & Wyvratt, 1990). Owing to their pharmacological activities the morpholine derivatives have received a great deal of attention in respect of their synthesis and crystal structures. Phthalimides and N-substituted phthalimides are an important class of compounds because of their interesting biological activities (Lima et al., 2002; Orzeszka et al., 2000; Bailleux et al., 1993).

Phthalimides have also served as starting materials and intermediates for synthesis of alkaloids (Couture et al., 1998) and pharmacophores (Couture et al., 1997).

The molecular structure of the title compound is illustrated in Fig. 1.

In the morpholine ring the average C—N, C—C and C—O bond distances [1.457 (2), 1.504 (2), 1.421 (2) A°] are in good agreement with earlier reports (Ramnathan et al., 1996). The morpholine ring adopts the usual chair conformation. This is in good agreement with structural data available from version 5.14 of the Cambridge Structural Database (Allen, 2002). The geometry of the phthalimide ring system is close to that in the related compound 4-(1,3-dioxoisoindolin-2-yl)benzaldehyde (Liu et al., 2004).

The sum of the angles around N1 is 358.60 (10)° indicating sp² hybridization. However the N1—C1 [1.399 (2) A° and N1—C8 [1.402 (2) A°] distances are intermediate between the average C_ar—Nsp³(pyramidal) [1.419 (17) A°]and C_ar—Nsp²(planar) [1.353 (7) A°] distances reported by Allen et al. (1987).

The crystal structure is stabilized by weak C—H···O hydrogen bonds (Table 1).

Related literature top

For related literature, see: Allen (2002); Allen et al. (1987); Bailleux et al. (1993); Couture et al. (1997, 1998); Fisher & Wyvratt (1990); Lima et al. (2002); Liu et al. (2004); Orzeszka et al. (2000); Ramnathan et al. (1996); Yoshioka (1995).

Experimental top

Phthalimide (14.7 g, 0.1mole) taken in a 250 ml beaker was dissolved in 20 ml dimethylformamide and 9.5 ml of 37%(w/v) aqueous formaldehyde (0.1 mole) was added and stirred well. Morpholine (9.0 ml, 0.1 mole) was slowly added to the beaker with stirring. The clear solution became oily. The oily mixture on continuous stirring gave the colourless solid product. The solid product was washed with cold water and finally with diethyl ether. The crude product was recrystallized from ethanol. It melts at 114°C.

Structure description top

Phthalimides have also served as starting materials and intermediates for synthesis of alkaloids (Couture et al., 1998) and pharmacophores (Couture et al., 1997).

The molecular structure of the title compound is illustrated in Fig. 1.

The crystal structure is stabilized by weak C—H···O hydrogen bonds (Table 1).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004) and SAINT-NT (Bruker,2004); data reduction: SAINT-NT (Bruker,2004) and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

Fig. 1. The structure of the title compound showing the atom numbering scheme with 30% probability displacement ellipsoids.

2-(Morpholin-4-ylmethyl)isoindole-1,3-dione top

Crystal data top

C₁₃H₁₄N₂O₃	F(000) = 520
M_r = 246.26	D_x = 1.354 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 114 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.3891 (6) Å	Cell parameters from 5593 reflections
b = 5.4617 (3) Å	θ = 1.7–31.0°
c = 23.5796 (16) Å	µ = 0.10 mm⁻¹
β = 92.209 (2)°	T = 293 K
V = 1208.27 (13) Å³	Prism, colorless
Z = 4	0.30 × 0.22 × 0.22 mm

Data collection top

Bruker APEXII diffractometer	3753 independent reflections
Radiation source: fine-focus sealed tube	2518 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω and φ scans	θ_max = 31.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −13→13
T_min = 0.971, T_max = 0.979	k = −7→7
15502 measured reflections	l = −33→33

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) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0714P)² + 0.1528P] where P = (F_o² + 2F_c²)/3
3753 reflections	(Δ/σ)_max = 0.003
171 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₃H₁₄N₂O₃	V = 1208.27 (13) Å³
M_r = 246.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.3891 (6) Å	µ = 0.10 mm⁻¹
b = 5.4617 (3) Å	T = 293 K
c = 23.5796 (16) Å	0.30 × 0.22 × 0.22 mm
β = 92.209 (2)°

Data collection top

Bruker APEXII diffractometer	3753 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2518 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.979	R_int = 0.026
15502 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.21 e Å⁻³
3753 reflections	Δρ_min = −0.19 e Å⁻³
171 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.53689 (11)	−0.2316 (2)	0.06952 (5)	0.0644 (4)
O2	0.83043 (11)	0.4355 (2)	0.07666 (4)	0.0618 (3)
O3	0.82872 (11)	−0.1431 (2)	0.27481 (4)	0.0616 (4)
N1	0.67568 (11)	0.11172 (19)	0.08750 (4)	0.0430 (3)
N2	0.66236 (10)	0.11859 (18)	0.19243 (4)	0.0375 (3)
C1	0.62829 (15)	−0.0907 (3)	0.05571 (5)	0.0484 (4)
C2	0.71093 (16)	−0.0865 (3)	0.00319 (5)	0.0572 (5)
C3	0.7080 (2)	−0.2493 (4)	−0.04214 (7)	0.0810 (7)
C4	0.7964 (3)	−0.1936 (6)	−0.08606 (8)	0.1082 (10)
C5	0.8805 (3)	0.0147 (6)	−0.08507 (8)	0.1069 (9)
C6	0.88466 (19)	0.1762 (4)	−0.03932 (7)	0.0804 (7)
C7	0.79708 (16)	0.1177 (3)	0.00476 (5)	0.0575 (5)
C8	0.77630 (14)	0.2498 (3)	0.05890 (5)	0.0474 (4)
C9	0.60573 (13)	0.2024 (2)	0.13835 (5)	0.0417 (3)
C10	0.81102 (12)	0.1807 (3)	0.20460 (5)	0.0455 (4)
C11	0.85198 (16)	0.1099 (3)	0.26483 (6)	0.0592 (5)
C12	0.68315 (16)	−0.2018 (3)	0.26299 (6)	0.0584 (5)
C13	0.63978 (15)	−0.1416 (2)	0.20251 (6)	0.0493 (4)
H3A	0.65007	−0.38755	−0.04295	0.0972*
H4A	0.79922	−0.29876	−0.11700	0.1298*
H5A	0.93613	0.04779	−0.11596	0.1282*
H6A	0.94246	0.31458	−0.03839	0.0965*
H9A	0.6128 (14)	0.381 (3)	0.1371 (6)	0.048 (4)*
H9B	0.5058 (16)	0.150 (3)	0.1337 (6)	0.048 (4)*
H10A	0.82499	0.35520	0.19949	0.0546*
H10B	0.87098	0.09469	0.17858	0.0546*
H11A	0.95183	0.14768	0.27247	0.0711*
H11B	0.79643	0.20552	0.29068	0.0711*
H12A	0.62398	−0.11068	0.28840	0.0700*
H12B	0.66817	−0.37498	0.26971	0.0700*
H13A	0.69587	−0.23740	0.17689	0.0592*
H13B	0.54008	−0.18188	0.19539	0.0592*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0630 (6)	0.0573 (7)	0.0717 (7)	0.0000 (5)	−0.0109 (5)	−0.0117 (5)
O2	0.0655 (6)	0.0595 (6)	0.0608 (6)	−0.0033 (5)	0.0090 (5)	0.0098 (5)
O3	0.0570 (6)	0.0753 (7)	0.0528 (6)	0.0141 (5)	0.0057 (4)	0.0212 (5)
N1	0.0499 (6)	0.0448 (6)	0.0343 (5)	0.0069 (4)	0.0036 (4)	−0.0027 (4)
N2	0.0392 (5)	0.0383 (5)	0.0352 (5)	0.0018 (4)	0.0053 (4)	−0.0002 (4)
C1	0.0546 (7)	0.0486 (7)	0.0411 (6)	0.0166 (6)	−0.0102 (5)	−0.0056 (5)
C2	0.0682 (9)	0.0679 (9)	0.0346 (6)	0.0358 (7)	−0.0094 (6)	−0.0042 (6)
C3	0.1056 (13)	0.0921 (13)	0.0432 (8)	0.0564 (11)	−0.0238 (8)	−0.0191 (8)
C4	0.141 (2)	0.148 (2)	0.0343 (8)	0.0961 (18)	−0.0133 (10)	−0.0177 (11)
C5	0.1146 (18)	0.169 (2)	0.0385 (9)	0.0920 (18)	0.0198 (10)	0.0219 (12)
C6	0.0766 (10)	0.1193 (15)	0.0467 (8)	0.0509 (11)	0.0190 (7)	0.0288 (9)
C7	0.0620 (8)	0.0761 (10)	0.0345 (6)	0.0342 (8)	0.0048 (5)	0.0101 (6)
C8	0.0489 (7)	0.0546 (8)	0.0388 (6)	0.0134 (6)	0.0035 (5)	0.0098 (5)
C9	0.0439 (6)	0.0431 (6)	0.0383 (6)	0.0084 (5)	0.0048 (5)	−0.0027 (5)
C10	0.0421 (6)	0.0508 (7)	0.0438 (7)	−0.0042 (5)	0.0045 (5)	0.0046 (5)
C11	0.0522 (7)	0.0769 (10)	0.0481 (8)	−0.0025 (7)	−0.0041 (6)	0.0049 (7)
C12	0.0638 (8)	0.0591 (9)	0.0532 (8)	0.0003 (7)	0.0154 (6)	0.0170 (7)
C13	0.0535 (7)	0.0430 (7)	0.0518 (7)	−0.0061 (5)	0.0058 (6)	0.0038 (5)

Geometric parameters (Å, º) top

O1—C1	1.2068 (18)	C7—C8	1.4858 (19)
O2—C8	1.2025 (19)	C10—C11	1.5074 (19)
O3—C11	1.420 (2)	C12—C13	1.504 (2)
O3—C12	1.4210 (18)	C3—H3A	0.9300
N1—C1	1.3987 (18)	C4—H4A	0.9300
N1—C8	1.4018 (17)	C5—H5A	0.9300
N1—C9	1.4748 (15)	C6—H6A	0.9300
N2—C9	1.4374 (15)	C9—H9A	0.978 (16)
N2—C10	1.4542 (15)	C9—H9B	0.983 (15)
N2—C13	1.4577 (15)	C10—H10A	0.9700
C1—C2	1.4867 (18)	C10—H10B	0.9700
C2—C3	1.390 (2)	C11—H11A	0.9700
C2—C7	1.377 (2)	C11—H11B	0.9700
C3—C4	1.386 (3)	C12—H12A	0.9700
C4—C5	1.385 (4)	C12—H12B	0.9700
C5—C6	1.393 (3)	C13—H13A	0.9700
C6—C7	1.387 (2)	C13—H13B	0.9700

O1···C13	3.2825 (18)	C4···H9Bⁱ	3.021 (15)
O1···C2ⁱ	3.3263 (18)	C8···H10B	3.0500
O2···C1ⁱⁱ	3.2358 (19)	C9···H12A^ix	2.9900
O2···C10	3.3336 (16)	C12···H4A^vii	2.9900
O2···C2ⁱⁱ	3.3054 (19)	C13···H9A^iv	3.035 (16)
O3···N2	2.8323 (14)	H3A···O1ⁱⁱⁱ	2.7800
O1···H9B	2.599 (16)	H4A···O3^x	2.6000
O1···H13A	2.8900	H4A···C12^x	2.9900
O1···H3Aⁱⁱⁱ	2.7800	H5A···H10B^viii	2.5000
O1···H9A^iv	2.727 (16)	H6A···O2^v	2.7200
O2···H9A	2.553 (14)	H9A···O1ⁱⁱ	2.727 (16)
O2···H6A^v	2.7200	H9A···O2	2.553 (14)
O3···H11A^vi	2.6400	H9A···C13ⁱⁱ	3.035 (16)
O3···H4A^vii	2.6000	H9A···H10A	2.4300
N2···O3	2.8323 (14)	H9A···H13Aⁱⁱ	2.4000
N1···H10B	2.7700	H9B···O1	2.599 (16)
N1···H13A	2.8400	H9B···H13B	2.3400
C1···O2^iv	3.2358 (19)	H9B···H12A^ix	2.6000
C1···C13	3.4702 (19)	H9B···C3ⁱ	2.941 (15)
C1···C2ⁱ	3.559 (2)	H9B···C4ⁱ	3.021 (15)
C2···O1ⁱ	3.3263 (18)	H10A···H9A	2.4300
C2···O2^iv	3.3054 (19)	H10A···H13Aⁱⁱ	2.5800
C2···C1ⁱ	3.559 (2)	H10B···N1	2.7700
C3···C6^iv	3.549 (3)	H10B···C8	3.0500
C5···C8^viii	3.563 (3)	H10B···H13A	2.4500
C5···C7^viii	3.582 (3)	H10B···H5A^viii	2.5000
C6···C7^viii	3.462 (2)	H11A···O3^xi	2.6400
C6···C3ⁱⁱ	3.549 (3)	H11B···H12A	2.3700
C6···C6^viii	3.395 (3)	H12A···H11B	2.3700
C7···C6^viii	3.462 (2)	H12A···C9^xii	2.9900
C7···C5^viii	3.582 (3)	H12A···H9B^xii	2.6000
C8···C10	3.4591 (17)	H13A···O1	2.8900
C8···C5^viii	3.563 (3)	H13A···N1	2.8400
C10···C8	3.4591 (17)	H13A···C1	3.0100
C10···O2	3.3336 (16)	H13A···H9A^iv	2.4000
C13···O1	3.2825 (18)	H13A···H10A^iv	2.5800
C13···C1	3.4702 (19)	H13A···H10B	2.4500
C1···H13A	3.0100	H13B···H9B	2.3400
C3···H9Bⁱ	2.941 (15)

C11—O3—C12	109.87 (11)	C5—C4—H4A	119.00
C1—N1—C8	111.95 (10)	C4—C5—H5A	119.00
C1—N1—C9	123.97 (10)	C6—C5—H5A	119.00
C8—N1—C9	122.68 (10)	C5—C6—H6A	122.00
C9—N2—C10	114.85 (9)	C7—C6—H6A	122.00
C9—N2—C13	113.83 (10)	N1—C9—H9A	106.1 (8)
C10—N2—C13	109.86 (10)	N1—C9—H9B	105.3 (9)
O1—C1—N1	125.05 (12)	N2—C9—H9A	108.7 (8)
O1—C1—C2	129.35 (14)	N2—C9—H9B	109.0 (9)
N1—C1—C2	105.59 (12)	H9A—C9—H9B	110.6 (12)
C1—C2—C3	129.44 (15)	N2—C10—H10A	110.00
C1—C2—C7	108.36 (12)	N2—C10—H10B	110.00
C3—C2—C7	122.20 (14)	C11—C10—H10A	110.00
C2—C3—C4	116.1 (2)	C11—C10—H10B	110.00
C3—C4—C5	121.7 (2)	H10A—C10—H10B	108.00
C4—C5—C6	122.2 (2)	O3—C11—H11A	109.00
C5—C6—C7	115.8 (2)	O3—C11—H11B	109.00
C2—C7—C6	122.06 (14)	C10—C11—H11A	109.00
C2—C7—C8	108.65 (12)	C10—C11—H11B	109.00
C6—C7—C8	129.29 (15)	H11A—C11—H11B	108.00
O2—C8—N1	124.74 (12)	O3—C12—H12A	109.00
O2—C8—C7	129.87 (13)	O3—C12—H12B	109.00
N1—C8—C7	105.39 (12)	C13—C12—H12A	109.00
N1—C9—N2	116.95 (10)	C13—C12—H12B	109.00
N2—C10—C11	109.52 (11)	H12A—C12—H12B	108.00
O3—C11—C10	111.75 (12)	N2—C13—H13A	110.00
O3—C12—C13	111.09 (12)	N2—C13—H13B	110.00
N2—C13—C12	109.39 (11)	C12—C13—H13A	110.00
C2—C3—H3A	122.00	C12—C13—H13B	110.00
C4—C3—H3A	122.00	H13A—C13—H13B	108.00
C3—C4—H4A	119.00

C12—O3—C11—C10	−58.12 (14)	N1—C1—C2—C3	178.32 (16)
C11—O3—C12—C13	58.81 (14)	N1—C1—C2—C7	−2.42 (16)
C8—N1—C1—C2	2.55 (15)	C1—C2—C7—C6	−178.17 (15)
C8—N1—C1—O1	−176.23 (14)	C3—C2—C7—C8	−179.25 (15)
C9—N1—C1—O1	−9.5 (2)	C7—C2—C3—C4	−0.4 (3)
C1—N1—C9—N2	95.41 (14)	C1—C2—C3—C4	178.78 (19)
C8—N1—C9—N2	−99.23 (13)	C1—C2—C7—C8	1.42 (17)
C1—N1—C8—C7	−1.72 (15)	C3—C2—C7—C6	1.2 (2)
C1—N1—C8—O2	178.10 (13)	C2—C3—C4—C5	−1.2 (4)
C9—N1—C8—O2	11.2 (2)	C3—C4—C5—C6	2.0 (4)
C9—N1—C8—C7	−168.67 (11)	C4—C5—C6—C7	−1.2 (4)
C9—N1—C1—C2	169.30 (11)	C5—C6—C7—C8	−179.85 (18)
C10—N2—C13—C12	57.89 (13)	C5—C6—C7—C2	−0.3 (3)
C9—N2—C13—C12	−171.72 (11)	C6—C7—C8—O2	−0.2 (3)
C10—N2—C9—N1	59.89 (14)	C2—C7—C8—O2	−179.71 (15)
C13—N2—C9—N1	−67.98 (13)	C6—C7—C8—N1	179.66 (16)
C9—N2—C10—C11	173.24 (11)	C2—C7—C8—N1	0.10 (16)
C13—N2—C10—C11	−56.92 (14)	N2—C10—C11—O3	57.48 (15)
O1—C1—C2—C7	176.30 (15)	O3—C12—C13—N2	−59.08 (15)
O1—C1—C2—C3	−3.0 (3)

Symmetry codes: (i) −x+1, −y, −z; (ii) x, y+1, z; (iii) −x+1, −y−1, −z; (iv) x, y−1, z; (v) −x+2, −y+1, −z; (vi) −x+2, y−1/2, −z+1/2; (vii) x, −y−1/2, z+1/2; (viii) −x+2, −y, −z; (ix) −x+1, y+1/2, −z+1/2; (x) x, −y−1/2, z−1/2; (xi) −x+2, y+1/2, −z+1/2; (xii) −x+1, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O3^x	0.9300	2.6000	3.424 (2)	149.00
C9—H9A···O2	0.978 (16)	2.553 (14)	2.9025 (16)	100.9 (9)

Symmetry code: (x) x, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₄N₂O₃
M_r	246.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.3891 (6), 5.4617 (3), 23.5796 (16)
β (°)	92.209 (2)
V (Å³)	1208.27 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.22 × 0.22

Data collection
Diffractometer	Bruker APEXII
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.971, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	15502, 3753, 2518
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.724

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.145, 1.03
No. of reflections	3753
No. of parameters	171
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.19

Computer programs: APEX2 (Bruker, 2004) and SAINT-NT (Bruker,2004), SAINT-NT (Bruker,2004) and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), PLATON (Spek, 2003).