6-(4-Meth­oxy­phen­yl)-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-carbaldehyde

Keck, P.R.W.E.F.; Schollmeyer, D.; Laufer, S.

doi:10.1107/S1600536811033022

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2417

doi:10.1107/S1600536811033022

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6-(4-Methoxyphenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-carbaldehyde

Peter R. W. E. F. Keck,^a Dieter Schollmeyer ^b and Stefan Laufer ^a ^*

^aEberhard-Karls-University Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany, and ^bUniversity Mainz, Institut of Organic Chemistry, Duesbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: stefan.laufer@uni-tuebingen.de

(Received 8 August 2011; accepted 15 August 2011; online 27 August 2011)

The 4-methoxyphenyl residue in the title compound, C₂₁H₁₉NO₂, is oriented at a dihedral angle of 54.6 (5)° with respect to the phenyl ring and at a dihedral angle of 52.5 (8)° with respect to the pyrrole ring of the pyrrolizine system. The phenyl ring is oriented at a dihedral angle of 36.2 (5)° with respect to the pyrrole ring. The methoxy group makes a C—C—O—C torsion angle of 3.8 (9)° with the attached benzene ring.

Related literature

For the biological activity of arylpyrrolizines as mPGES-1 inhibitors, see: Liedtke et al. (2009 ). For dual COX/5-LOX inhibitors, see: Laufer (2001 ); Tries & Laufer (2001 ).

Experimental

Crystal data

C₂₁H₁₉NO₂
M_r = 317.37
Monoclinic, P 2₁ /n
a = 12.2276 (17) Å
b = 9.1557 (10) Å
c = 15.462 (2) Å
β = 104.174 (11)°
V = 1678.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 193 K
0.30 × 0.20 × 0.07 mm

Data collection

Stoe IPDS 2T diffractometer
23718 measured reflections
4043 independent reflections
2868 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.102
S = 1.02
4043 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2010); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2010); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811033022/si2370sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033022/si2370Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811033022/si2370Isup3.cml

checkCIF report

Comment top

Based on ML3000 (Tries & Laufer, 2001 and Laufer, 2001) as dual COX/5-LOX inhibitor, we synthesized and evaluated inhibitors for the microsomal prostaglandin E₂ synthase-1 (mPGES-1) (Liedtke et al., 2009). The title compound was synthesized to obtain a template with a reactive group in position 5 of the pyrrolizine moiety which lead to series of differend derivates of the arylpyrrolizine scaffold.

Towards the unsaturated and planar part of the pyrrolizine residue the 4-methoxyphenyl residue is oriented at a dihedral angle of 52.5 (8)° and the plain phenyl ring is oriented at a dihedral angle of 36.2 (5)°. The two phenyl rings are oriented at a dihedral angle of 54.6 (5)° and both centromers show a distance of 4.89 (7) Å. The distance between the para C atoms of the rings (C13, C21) is 6.55 (9) Å. The methoxy group shows a torsion angle of 3.8 (9)° towards the phenyl ring.

Related literature top

For the biological activity of arylpyrrolizines as mPGES-1 inhibitors, see: Liedtke et al. (2009). For dual COX/5-LOX inhibitors, see: Laufer (2001); Tries & Laufer (2001).

Experimental top

The compound was prepared by Vilsmeyer reaction. Phosphoryl chloride (0.484 ml, 5.31 mmol) is added dropwise to ice-cooled solution of 1.18 ml dimethylformamide and 6-(4-methoxyphenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine (1.5 g, 5.11 mmol); the temperature is kept under 293 K during the addition. Then the mixture is stirred for 1 h at room temperature. Finally the mixture is heated to 333 K for 1 h. The mixture was cooled to 273 K, quenched by water and adjusted to pH 6 with aqueous sodium hydroxide solution 10%.

The product was collected as precipitated solid by filtration, was dissolved in dichloromethane and washed with water three times and finally dried over anhydrous sodium sulfate. The product was concentrated under vacuum. The residue was purified by column chromatography (SiO₂, n-hexane / ethyl acetate: 2 + 1). Crystals of the title compound were obtained by slow evaporation of ethanol at room temperature.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2010); cell refinement: X-AREA (Stoe & Cie, 2010); data reduction: X-RED (Stoe & Cie, 2010); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. View of compound (I). Displacement ellipsoids are drawn at the 50% probability level.

6-(4-Methoxyphenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-carbaldehyde top

Crystal data top

C₂₁H₁₉NO₂	F(000) = 672
M_r = 317.37	D_x = 1.256 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 18580 reflections
a = 12.2276 (17) Å	θ = 2.4–30°
b = 9.1557 (10) Å	µ = 0.08 mm⁻¹
c = 15.462 (2) Å	T = 193 K
β = 104.174 (11)°	Plate, light brown
V = 1678.3 (4) Å³	0.30 × 0.20 × 0.07 mm
Z = 4

Data collection top

Stoe IPDS 2T diffractometer	2868 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	R_int = 0.067
Detector resolution: 6.67 pixels mm^-1	θ_max = 28.0°, θ_min = 2.4°
rotation method scans	h = −16→15
23718 measured reflections	k = −12→12
4043 independent reflections	l = −20→20

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.047P)² + 0.1927P] where P = (F_o² + 2F_c²)/3
4043 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₁H₁₉NO₂	V = 1678.3 (4) Å³
M_r = 317.37	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.2276 (17) Å	µ = 0.08 mm⁻¹
b = 9.1557 (10) Å	T = 193 K
c = 15.462 (2) Å	0.30 × 0.20 × 0.07 mm
β = 104.174 (11)°

Data collection top

Stoe IPDS 2T diffractometer	2868 reflections with I > 2σ(I)
23718 measured reflections	R_int = 0.067
4043 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.02	Δρ_max = 0.17 e Å⁻³
4043 reflections	Δρ_min = −0.16 e Å⁻³
218 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	0.06152 (12)	0.14978 (15)	0.66247 (9)	0.0393 (3)
H1A	0.0946	0.2238	0.7081	0.047*
H1B	0.1108	0.0625	0.6709	0.047*
C2	−0.05958 (14)	0.10999 (18)	0.66633 (10)	0.0517 (4)
H2A	−0.0599	0.0171	0.6991	0.062*
H2B	−0.0917	0.1877	0.6972	0.062*
C3	−0.12865 (12)	0.09433 (16)	0.56986 (10)	0.0432 (3)
H3A	−0.1354	−0.0092	0.5508	0.052*
H3B	−0.2050	0.1368	0.5617	0.052*
N4	−0.06033 (9)	0.17804 (11)	0.52170 (7)	0.0359 (2)
C5	−0.07535 (10)	0.22928 (14)	0.43583 (9)	0.0352 (3)
C6	0.02545 (10)	0.29896 (13)	0.43203 (8)	0.0319 (3)
C7	0.10129 (10)	0.28749 (13)	0.51738 (8)	0.0319 (3)
C7A	0.04412 (10)	0.21009 (13)	0.57039 (8)	0.0339 (3)
C8	−0.17589 (11)	0.20663 (15)	0.36689 (10)	0.0430 (3)
H8	−0.1776	0.2450	0.3095	0.052*
O9	−0.25971 (9)	0.14180 (13)	0.37601 (8)	0.0582 (3)
C10	0.05027 (10)	0.36298 (13)	0.35126 (8)	0.0321 (3)
C11	−0.01913 (10)	0.46703 (13)	0.29946 (8)	0.0343 (3)
H11	−0.0849	0.4985	0.3165	0.041*
C12	0.00522 (10)	0.52607 (14)	0.22357 (8)	0.0358 (3)
H12	−0.0439	0.5962	0.1889	0.043*
C13	0.10122 (11)	0.48215 (15)	0.19885 (8)	0.0370 (3)
C14	0.17152 (11)	0.37719 (16)	0.24926 (9)	0.0407 (3)
H14	0.2371	0.3459	0.2320	0.049*
C15	0.14613 (10)	0.31872 (15)	0.32406 (9)	0.0369 (3)
H15	0.1946	0.2470	0.3578	0.044*
O16	0.13358 (9)	0.53308 (12)	0.12557 (7)	0.0498 (3)
C17	0.06605 (15)	0.64537 (19)	0.07522 (11)	0.0580 (4)
H17A	−0.0108	0.6088	0.0513	0.087*
H17B	0.0985	0.6748	0.0259	0.087*
H17C	0.0640	0.7297	0.1138	0.087*
C18	0.21576 (10)	0.34911 (13)	0.54706 (8)	0.0315 (3)
C19	0.24241 (11)	0.48377 (14)	0.51540 (9)	0.0397 (3)
H19	0.1856	0.5375	0.4749	0.048*
C20	0.35037 (12)	0.54021 (16)	0.54212 (10)	0.0462 (3)
H20	0.3675	0.6313	0.5192	0.055*
C21	0.43355 (12)	0.46435 (16)	0.60222 (9)	0.0458 (3)
H21	0.5078	0.5029	0.6203	0.055*
C22	0.40810 (11)	0.33296 (16)	0.63563 (9)	0.0428 (3)
H22	0.4646	0.2817	0.6778	0.051*
C23	0.30042 (11)	0.27471 (14)	0.60821 (8)	0.0364 (3)
H23	0.2841	0.1833	0.6313	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0432 (7)	0.0409 (7)	0.0367 (7)	0.0017 (5)	0.0154 (5)	0.0031 (5)
C2	0.0539 (9)	0.0616 (9)	0.0454 (8)	−0.0123 (7)	0.0234 (7)	0.0019 (7)
C3	0.0396 (7)	0.0450 (7)	0.0501 (8)	−0.0072 (6)	0.0209 (6)	0.0019 (6)
N4	0.0306 (5)	0.0407 (5)	0.0386 (6)	−0.0036 (4)	0.0129 (4)	0.0008 (5)
C5	0.0296 (6)	0.0411 (6)	0.0361 (6)	−0.0010 (5)	0.0102 (5)	−0.0007 (5)
C6	0.0268 (6)	0.0368 (6)	0.0324 (6)	0.0011 (4)	0.0080 (5)	−0.0010 (5)
C7	0.0289 (6)	0.0363 (6)	0.0314 (6)	0.0011 (5)	0.0094 (5)	−0.0005 (5)
C7A	0.0323 (6)	0.0369 (6)	0.0342 (6)	0.0004 (5)	0.0116 (5)	−0.0018 (5)
C8	0.0310 (7)	0.0497 (7)	0.0469 (8)	−0.0026 (6)	0.0070 (6)	−0.0037 (6)
O9	0.0336 (6)	0.0685 (7)	0.0695 (7)	−0.0141 (5)	0.0069 (5)	−0.0018 (6)
C10	0.0260 (6)	0.0391 (6)	0.0304 (6)	−0.0005 (5)	0.0055 (4)	−0.0013 (5)
C11	0.0271 (6)	0.0411 (6)	0.0349 (6)	0.0036 (5)	0.0079 (5)	−0.0021 (5)
C12	0.0323 (6)	0.0390 (6)	0.0343 (6)	0.0043 (5)	0.0046 (5)	0.0034 (5)
C13	0.0326 (6)	0.0461 (7)	0.0323 (6)	−0.0012 (5)	0.0082 (5)	0.0038 (5)
C14	0.0270 (6)	0.0565 (8)	0.0405 (7)	0.0073 (5)	0.0120 (5)	0.0070 (6)
C15	0.0267 (6)	0.0470 (7)	0.0362 (6)	0.0056 (5)	0.0059 (5)	0.0064 (5)
O16	0.0450 (6)	0.0659 (6)	0.0418 (5)	0.0064 (5)	0.0170 (4)	0.0167 (5)
C17	0.0609 (10)	0.0662 (10)	0.0462 (9)	0.0048 (8)	0.0120 (7)	0.0216 (8)
C18	0.0286 (6)	0.0388 (6)	0.0278 (6)	−0.0005 (5)	0.0085 (4)	−0.0034 (5)
C19	0.0360 (7)	0.0394 (6)	0.0413 (7)	−0.0013 (5)	0.0047 (5)	0.0023 (5)
C20	0.0433 (8)	0.0435 (7)	0.0496 (8)	−0.0106 (6)	0.0071 (6)	0.0017 (6)
C21	0.0346 (7)	0.0561 (8)	0.0433 (8)	−0.0096 (6)	0.0033 (6)	−0.0054 (6)
C22	0.0337 (7)	0.0550 (8)	0.0355 (7)	0.0004 (6)	0.0005 (5)	0.0007 (6)
C23	0.0339 (6)	0.0435 (7)	0.0307 (6)	−0.0004 (5)	0.0057 (5)	0.0025 (5)

Geometric parameters (Å, º) top

C1—C7A	1.4929 (18)	C11—H11	0.9500
C1—C2	1.540 (2)	C12—C13	1.3805 (18)
C1—H1A	0.9900	C12—H12	0.9500
C1—H1B	0.9900	C13—O16	1.3701 (16)
C2—C3	1.530 (2)	C13—C14	1.3935 (18)
C2—H2A	0.9900	C14—C15	1.3771 (19)
C2—H2B	0.9900	C14—H14	0.9500
C3—N4	1.4645 (16)	C15—H15	0.9500
C3—H3A	0.9900	O16—C17	1.4247 (18)
C3—H3B	0.9900	C17—H17A	0.9800
N4—C7A	1.3466 (16)	C17—H17B	0.9800
N4—C5	1.3773 (17)	C17—H17C	0.9800
C5—C6	1.4019 (17)	C18—C19	1.3943 (18)
C5—C8	1.4314 (18)	C18—C23	1.3965 (17)
C6—C7	1.4189 (17)	C19—C20	1.3833 (19)
C6—C10	1.4768 (17)	C19—H19	0.9500
C7—C7A	1.3941 (17)	C20—C21	1.385 (2)
C7—C18	1.4743 (17)	C20—H20	0.9500
C8—O9	1.2221 (17)	C21—C22	1.375 (2)
C8—H8	0.9500	C21—H21	0.9500
C10—C11	1.3915 (17)	C22—C23	1.3873 (18)
C10—C15	1.3987 (17)	C22—H22	0.9500
C11—C12	1.3889 (18)	C23—H23	0.9500

C7A—C1—C2	102.16 (11)	C12—C11—H11	119.1
C7A—C1—H1A	111.3	C10—C11—H11	119.1
C2—C1—H1A	111.3	C13—C12—C11	119.56 (11)
C7A—C1—H1B	111.3	C13—C12—H12	120.2
C2—C1—H1B	111.3	C11—C12—H12	120.2
H1A—C1—H1B	109.2	O16—C13—C12	124.55 (12)
C3—C2—C1	106.90 (11)	O16—C13—C14	115.71 (12)
C3—C2—H2A	110.3	C12—C13—C14	119.73 (12)
C1—C2—H2A	110.3	C15—C14—C13	120.19 (12)
C3—C2—H2B	110.3	C15—C14—H14	119.9
C1—C2—H2B	110.3	C13—C14—H14	119.9
H2A—C2—H2B	108.6	C14—C15—C10	121.18 (12)
N4—C3—C2	101.49 (11)	C14—C15—H15	119.4
N4—C3—H3A	111.5	C10—C15—H15	119.4
C2—C3—H3A	111.5	C13—O16—C17	116.83 (12)
N4—C3—H3B	111.5	O16—C17—H17A	109.5
C2—C3—H3B	111.5	O16—C17—H17B	109.5
H3A—C3—H3B	109.3	H17A—C17—H17B	109.5
C7A—N4—C5	110.43 (10)	O16—C17—H17C	109.5
C7A—N4—C3	114.25 (11)	H17A—C17—H17C	109.5
C5—N4—C3	135.27 (11)	H17B—C17—H17C	109.5
N4—C5—C6	106.52 (11)	C19—C18—C23	118.09 (11)
N4—C5—C8	123.78 (11)	C19—C18—C7	120.98 (11)
C6—C5—C8	129.66 (12)	C23—C18—C7	120.93 (11)
C5—C6—C7	107.96 (11)	C20—C19—C18	120.89 (12)
C5—C6—C10	125.52 (11)	C20—C19—H19	119.6
C7—C6—C10	126.37 (11)	C18—C19—H19	119.6
C7A—C7—C6	106.08 (11)	C19—C20—C21	120.23 (13)
C7A—C7—C18	125.87 (11)	C19—C20—H20	119.9
C6—C7—C18	128.00 (11)	C21—C20—H20	119.9
N4—C7A—C7	108.99 (11)	C22—C21—C20	119.64 (13)
N4—C7A—C1	110.30 (11)	C22—C21—H21	120.2
C7—C7A—C1	140.70 (12)	C20—C21—H21	120.2
O9—C8—C5	125.17 (14)	C21—C22—C23	120.45 (13)
O9—C8—H8	117.4	C21—C22—H22	119.8
C5—C8—H8	117.4	C23—C22—H22	119.8
C11—C10—C15	117.59 (11)	C22—C23—C18	120.67 (12)
C11—C10—C6	122.40 (11)	C22—C23—H23	119.7
C15—C10—C6	120.01 (11)	C18—C23—H23	119.7
C12—C11—C10	121.74 (12)

C7A—C1—C2—C3	21.22 (15)	C5—C6—C10—C11	55.01 (18)
C1—C2—C3—N4	−21.05 (15)	C7—C6—C10—C11	−129.87 (14)
C2—C3—N4—C7A	13.49 (15)	C5—C6—C10—C15	−124.61 (14)
C2—C3—N4—C5	−169.27 (14)	C7—C6—C10—C15	50.51 (18)
C7A—N4—C5—C6	−0.94 (14)	C15—C10—C11—C12	−0.26 (18)
C3—N4—C5—C6	−178.26 (13)	C6—C10—C11—C12	−179.88 (11)
C7A—N4—C5—C8	177.15 (12)	C10—C11—C12—C13	−0.67 (19)
C3—N4—C5—C8	−0.2 (2)	C11—C12—C13—O16	−179.91 (12)
N4—C5—C6—C7	0.34 (14)	C11—C12—C13—C14	1.2 (2)
C8—C5—C6—C7	−177.60 (13)	O16—C13—C14—C15	−179.78 (13)
N4—C5—C6—C10	176.21 (11)	C12—C13—C14—C15	−0.8 (2)
C8—C5—C6—C10	−1.7 (2)	C13—C14—C15—C10	−0.2 (2)
C5—C6—C7—C7A	0.35 (14)	C11—C10—C15—C14	0.68 (19)
C10—C6—C7—C7A	−175.48 (11)	C6—C10—C15—C14	−179.68 (12)
C5—C6—C7—C18	−177.23 (12)	C12—C13—O16—C17	3.9 (2)
C10—C6—C7—C18	6.9 (2)	C14—C13—O16—C17	−177.17 (13)
C5—N4—C7A—C7	1.19 (14)	C7A—C7—C18—C19	−142.11 (13)
C3—N4—C7A—C7	179.11 (10)	C6—C7—C18—C19	35.02 (19)
C5—N4—C7A—C1	−177.99 (10)	C7A—C7—C18—C23	37.43 (18)
C3—N4—C7A—C1	−0.06 (15)	C6—C7—C18—C23	−145.44 (13)
C6—C7—C7A—N4	−0.93 (14)	C23—C18—C19—C20	1.60 (19)
C18—C7—C7A—N4	176.71 (11)	C7—C18—C19—C20	−178.85 (13)
C6—C7—C7A—C1	177.85 (15)	C18—C19—C20—C21	−1.1 (2)
C18—C7—C7A—C1	−4.5 (2)	C19—C20—C21—C22	−0.4 (2)
C2—C1—C7A—N4	−13.35 (14)	C20—C21—C22—C23	1.3 (2)
C2—C1—C7A—C7	167.88 (16)	C21—C22—C23—C18	−0.7 (2)
N4—C5—C8—O9	1.0 (2)	C19—C18—C23—C22	−0.70 (19)
C6—C5—C8—O9	178.61 (14)	C7—C18—C23—C22	179.74 (12)

Experimental details

Crystal data
Chemical formula	C₂₁H₁₉NO₂
M_r	317.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	193
a, b, c (Å)	12.2276 (17), 9.1557 (10), 15.462 (2)
β (°)	104.174 (11)
V (Å³)	1678.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.07

Data collection
Diffractometer	Stoe IPDS 2T diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	23718, 4043, 2868
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.102, 1.02
No. of reflections	4043
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.16

Computer programs: X-AREA (Stoe & Cie, 2010), X-RED (Stoe & Cie, 2010), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Laufer, S. (2001). Inflammopharmacology, 9, 101–112. CrossRef CAS Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2010). X-AREA and X-RED. Stoe & Cie GmbH, Darmstadt, Germany. Google Scholar
Tries, S. & Laufer, S. (2001). Inflammopharmacology, 9, 113–124. CrossRef CAS Google Scholar