2-Meth­oxy-9-phenoxy­acridine

Trzybiński, D.; Zadykowicz, B.; Krzymiński, K.; Sikorski, A.; Błażejowski, J.

doi:10.1107/S1600536810008962

2-Methoxy-9-phenoxyacridine

D. Trzybiński, B. Zadykowicz, K. Krzymiński, A. Sikorski and J. Błażejowski

The molecules in the crystal structure of the title compound, C₂₀H₁₅NO₂, form inversion dimers connected through the C—H

N and π–π interactions. These dimers are further linked by C—H

π interactions. The methoxy group is nearly coplanar with the acridine ring system [dihedral angle = 4.5 (1)°], whereas the phenoxy fragment is nearly perpendicular to it [dihedral angle = 85.0 (1)°]. The mean planes of the acridine ring systems are either parallel or inclined at angles of 14.3 (1), 65.4 (1) and 67.3 (1)° in the crystal.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810008962/ng2741sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810008962/ng2741Isup2.hkl Contains datablock I

CCDC reference: 774271

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
R factor = 0.029
wR factor = 0.086
Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          4
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........    <I>CG</
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........    <I>CG</
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........    <I>CG</

   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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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

9-Phenoxyacridines are convenient precursors of 9-substituted acridines owing to their excellent stability during storage at room temperature (Albert, 1966; Acheson, 1973); they effectively react with hydrochlorides of various amines to yield the respective 9-acridinamines. The compounds belonging to this group were proposed as fluorescent labels in medicinal diagnostics (Ueyama et al., 2002) and checked for anti-bacterial (Lebekhov & Samarin, 1969) and anti-inflammatory (Chen et al., 2002) activities. Here we demonstrate the structure of 9-phenoxyacridine substituted with the methoxy group at the acridine moiety; we investigated the parent molecule (i.e. 9-phenoxyacridine) earlier (Ebead et al., 2005). Such substitution may affect spectral features of 9-phenoxyacridine and facilitate its conversion to medically interesting derivatives (Demeunynck et al., 2001).

In the crystal structure, the inversely oriented molecules form dimers through π–π interactions involving acridine skeletons (Table 2, Fig. 2) and C(aromatic)–H···N interactions (Table 1, Fig. 2). These dimers are linked in the crystal lattice by C(aliphatic, aromatic)–H···π interactions (Table 1, Fig. 2). The C–H···N interactions are of the hydrogen bond type (Steiner, 1999). The C–H···π interactions (Takahashi et al., 2001), like the π–π interactions (Hunter et al., 2001) should be of an attractive nature. The crystal structure is stabilized by a network of these short-range specific interactions and by non-specific dispersive interactions between adjacent molecules.

In the title compound (Fig. 1), the bond lengths and angles characterizing the geometry of the acridine moiety are typical of acridine based derivatives (Ebead et al., 2005; Sikorski et al., 2007). With a respective average deviation from planarity of 0.0147 (2) Å and 0.0072 (2) Å, the acridine and benzene ring systems are oriented at 85.0 (1)°, i.e. they are nearly perpendicular to each other. On the other hand, the methoxy group is almost co-planar with the acridine skeleton (the angle between the mean plane of the acridine moiety and the plane delineated by C2, O15 and C16 is 4.5 (1)°). C9, N10 and O17 are arranged almost linearly (N10···C9–O17 angle = 174.9 (1)°). The mean planes of the adjacent acridine moieties are either parallel (they remain at an angle of 0.0 (1)° – in dimers) or inclined at angles of 14.3 (1)°, 65.4 (1)° and 67.3 (1)° in the lattice. The molecular structure of the compound investigated is similar to that of 9-phenoxyacridine (Ebead et al., 2005).

Related literature top

For general background to 9-phenoxyacridines, see: Acheson (1973); Albert (1966); Chen et al. (2002); Demeunynck et al. (2001); Lebekhov & Samarin (1969); Ueyama et al. (2002). For related structures, see: Ebead et al. (2005); Sikorski et al. (2007). For intermolecular interactions, see: Hunter et al. (2001); Mazik et al. (2000); Takahashi et al. (2001). For the synthesis, see: Acheson (1973); Chen et al. (2002); Duprè & Robinson (1945).

Experimental top

2-Methoxy-9-chloroacridine was prepared by heating 2-[(2-methoxyphenyl)amino]benzoic acid, obtained as described elsewhere (Acheson, 1973), with a sevenfold molar excess of POCl₃ (400 K, 3 h). The excess POCl₃ was subsequently removed under reduced pressure. The residue was dispersed in CHCl₃, stirred in the presence of a mixture of ice and aqueous ammonia, separated by filtration and dried. The crude product was purified chromatographically (neutral Al₂O₃, CHCl₃/toluene, 1/1 v/v). The obtained 2-methoxy-9-chloroacridine was added to the solution of NaOH in phenol (sevenfold molar excess) in equimolar to NaOH amount, at 373 K under continuous stirring. The reactant mixture was kept at 373 K for 1.5 h, subsequently poured into 2M aq NaOH and stored at room temperature overnight. The precipitate was separated by filtration, washed with water and dried (Duprè & Robinson, 1945; Chen et al., 2002). Light-brown crystals of 2-methoxy-9-phenoxyacridine suitable for X-Ray investigations were grown from absolute ethanol solution (m.p. 415-417 K).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atom labeling scheme. Displacement ellipsoids are drawn at the 25% probability level and H atoms are shown as small spheres of arbitrary radius. Cg1, Cg2, Cg3 and Cg4 denote the ring centroids.
	Fig. 2. The arrangement of the molecules in the crystal structure. The C–H···N and C–H···π interactions are represented by dashed lines and π–π interactions by dotted lines. [Symmetry codes: (i) –x, –y, –z+1; (ii) x+1/2, –y+1/2, –z+1; (iii) x+1/2, y, –z+1/2; (iv) x–1, y, z.]

2-Methoxy-9-phenoxyacridine top

Crystal data top

C₂₀H₁₅NO₂	F(000) = 1264
M_r = 301.33	D_x = 1.294 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 32561 reflections
a = 8.3042 (2) Å	θ = 3.0–29.3°
b = 15.5101 (4) Å	µ = 0.08 mm⁻¹
c = 24.0192 (6) Å	T = 295 K
V = 3093.65 (13) Å³	Plate, light-brown
Z = 8	0.50 × 0.25 × 0.10 mm

Data collection top

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	2747 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2322 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 10.4002 pixels mm^-1	θ_max = 25.1°, θ_min = 3.0°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −18→18
T_min = 0.890, T_max = 0.994	l = −28→28
56825 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)] = 0.029	H-atom parameters constrained
wR(F²) = 0.086	w = 1/[σ²(F_o²) + (0.048P)² + 0.2828P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
2747 reflections	Δρ_max = 0.15 e Å⁻³
210 parameters	Δρ_min = −0.11 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0046 (6)

Crystal data top

C₂₀H₁₅NO₂	V = 3093.65 (13) Å³
M_r = 301.33	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.3042 (2) Å	µ = 0.08 mm⁻¹
b = 15.5101 (4) Å	T = 295 K
c = 24.0192 (6) Å	0.50 × 0.25 × 0.10 mm

Data collection top

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	2747 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	2322 reflections with I > 2σ(I)
T_min = 0.890, T_max = 0.994	R_int = 0.024
56825 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.10	Δρ_max = 0.15 e Å⁻³
2747 reflections	Δρ_min = −0.11 e Å⁻³
210 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.18244 (13)	0.00760 (7)	0.34444 (4)	0.0442 (3)
H1	0.1362	0.0364	0.3145	0.053*
C2	0.26680 (14)	−0.06681 (7)	0.33602 (5)	0.0498 (3)
C3	0.33776 (16)	−0.11161 (8)	0.38157 (5)	0.0560 (3)
H3	0.3938	−0.1626	0.3751	0.067*
C4	0.32483 (15)	−0.08118 (8)	0.43386 (5)	0.0525 (3)
H4	0.3731	−0.1112	0.4629	0.063*
C5	0.13635 (15)	0.12529 (8)	0.56536 (5)	0.0522 (3)
H5	0.1883	0.0946	0.5934	0.063*
C6	0.05228 (16)	0.19741 (9)	0.57843 (5)	0.0591 (3)
H6	0.0471	0.2155	0.6153	0.071*
C7	−0.02759 (15)	0.24540 (8)	0.53666 (5)	0.0573 (3)
H7	−0.0854	0.2945	0.5464	0.069*
C8	−0.02090 (13)	0.22067 (7)	0.48256 (5)	0.0478 (3)
H8	−0.0737	0.2530	0.4555	0.057*
C9	0.08142 (12)	0.11619 (6)	0.41230 (4)	0.0383 (2)
N10	0.23001 (11)	0.02343 (6)	0.49857 (4)	0.0460 (2)
C11	0.16565 (11)	0.04083 (6)	0.39947 (4)	0.0389 (2)
C12	0.23839 (12)	−0.00369 (7)	0.44563 (4)	0.0416 (3)
C13	0.06662 (12)	0.14545 (7)	0.46691 (4)	0.0397 (3)
C14	0.14617 (12)	0.09591 (7)	0.50938 (4)	0.0421 (3)
O15	0.29423 (13)	−0.10503 (6)	0.28557 (3)	0.0676 (3)
C16	0.2364 (2)	−0.06180 (10)	0.23706 (5)	0.0749 (4)
H16A	0.2695	−0.0929	0.2045	0.112*
H16B	0.2799	−0.0045	0.2358	0.112*
H16C	0.1210	−0.0589	0.2382	0.112*
O17	0.02052 (8)	0.16615 (5)	0.36901 (3)	0.0441 (2)
C18	−0.13908 (11)	0.15439 (6)	0.35297 (4)	0.0352 (2)
C19	−0.24472 (13)	0.10027 (6)	0.38029 (4)	0.0410 (3)
H19	−0.2123	0.0697	0.4117	0.049*
C20	−0.40022 (14)	0.09241 (8)	0.35996 (5)	0.0508 (3)
H20	−0.4727	0.0561	0.3779	0.061*
C21	−0.44883 (14)	0.13772 (9)	0.31347 (5)	0.0572 (3)
H21	−0.5530	0.1314	0.2998	0.069*
C22	−0.34193 (15)	0.19255 (9)	0.28733 (5)	0.0552 (3)
H22	−0.3745	0.2235	0.2561	0.066*
C23	−0.18710 (13)	0.20176 (7)	0.30720 (4)	0.0441 (3)
H23	−0.1158	0.2395	0.2900	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0460 (6)	0.0434 (6)	0.0434 (6)	−0.0019 (5)	−0.0025 (5)	0.0079 (5)
C2	0.0564 (7)	0.0440 (6)	0.0489 (7)	−0.0009 (5)	0.0051 (5)	0.0015 (5)
C3	0.0648 (8)	0.0420 (6)	0.0612 (8)	0.0114 (5)	0.0039 (6)	0.0071 (5)
C4	0.0579 (7)	0.0453 (6)	0.0544 (7)	0.0097 (5)	−0.0032 (5)	0.0141 (5)
C5	0.0596 (7)	0.0521 (7)	0.0450 (6)	−0.0066 (6)	−0.0065 (5)	0.0042 (5)
C6	0.0686 (8)	0.0579 (8)	0.0508 (7)	−0.0073 (6)	0.0007 (6)	−0.0078 (6)
C7	0.0558 (7)	0.0500 (7)	0.0661 (8)	0.0012 (6)	0.0028 (6)	−0.0079 (6)
C8	0.0427 (6)	0.0436 (6)	0.0570 (7)	−0.0004 (5)	−0.0019 (5)	0.0039 (5)
C9	0.0339 (5)	0.0377 (5)	0.0432 (6)	−0.0040 (4)	−0.0049 (4)	0.0119 (4)
N10	0.0487 (5)	0.0440 (5)	0.0452 (5)	0.0003 (4)	−0.0051 (4)	0.0099 (4)
C11	0.0354 (5)	0.0374 (5)	0.0438 (6)	−0.0039 (4)	−0.0014 (4)	0.0091 (4)
C12	0.0405 (5)	0.0401 (6)	0.0442 (6)	−0.0017 (4)	−0.0021 (4)	0.0095 (5)
C13	0.0343 (5)	0.0380 (6)	0.0469 (6)	−0.0058 (4)	−0.0019 (4)	0.0067 (4)
C14	0.0414 (6)	0.0407 (6)	0.0443 (6)	−0.0071 (4)	−0.0030 (4)	0.0068 (5)
O15	0.0937 (7)	0.0575 (5)	0.0515 (5)	0.0130 (5)	0.0051 (5)	−0.0031 (4)
C16	0.1016 (11)	0.0740 (9)	0.0492 (8)	0.0065 (8)	−0.0016 (7)	−0.0043 (7)
O17	0.0378 (4)	0.0443 (4)	0.0502 (4)	−0.0016 (3)	−0.0052 (3)	0.0173 (3)
C18	0.0366 (5)	0.0341 (5)	0.0349 (5)	0.0029 (4)	−0.0004 (4)	−0.0010 (4)
C19	0.0472 (6)	0.0367 (5)	0.0393 (5)	−0.0018 (4)	−0.0032 (4)	0.0043 (4)
C20	0.0470 (6)	0.0497 (7)	0.0556 (7)	−0.0106 (5)	−0.0013 (5)	0.0020 (5)
C21	0.0472 (7)	0.0685 (8)	0.0560 (7)	−0.0050 (6)	−0.0155 (5)	0.0019 (6)
C22	0.0540 (7)	0.0698 (8)	0.0418 (6)	0.0042 (6)	−0.0099 (5)	0.0111 (6)
C23	0.0452 (6)	0.0500 (6)	0.0369 (5)	0.0033 (5)	0.0037 (4)	0.0086 (5)

Geometric parameters (Å, º) top

C1—C2	1.3651 (16)	N10—C12	1.3413 (14)
C1—C11	1.4256 (15)	N10—C14	1.3476 (14)
C1—H1	0.9300	C11—C12	1.4391 (14)
C2—O15	1.3681 (14)	C13—C14	1.4378 (14)
C2—C3	1.4237 (17)	O15—C16	1.4276 (16)
C3—C4	1.3460 (17)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C12	1.4282 (16)	C16—H16C	0.9600
C4—H4	0.9300	O17—C18	1.3922 (12)
C5—C6	1.3554 (19)	C18—C19	1.3801 (14)
C5—C14	1.4220 (16)	C18—C23	1.3812 (14)
C5—H5	0.9300	C19—C20	1.3859 (15)
C6—C7	1.4144 (18)	C19—H19	0.9300
C6—H6	0.9300	C20—C21	1.3797 (17)
C7—C8	1.3560 (16)	C20—H20	0.9300
C7—H7	0.9300	C21—C22	1.3805 (18)
C8—C13	1.4250 (16)	C21—H21	0.9300
C8—H8	0.9300	C22—C23	1.3788 (16)
C9—O17	1.3920 (12)	C22—H22	0.9300
C9—C13	1.3934 (14)	C23—H23	0.9300
C9—C11	1.3965 (15)

C2—C1—C11	119.54 (10)	C4—C12—C11	117.54 (10)
C2—C1—H1	120.2	C9—C13—C8	124.06 (9)
C11—C1—H1	120.2	C9—C13—C14	116.95 (9)
C1—C2—O15	125.66 (10)	C8—C13—C14	118.99 (10)
C1—C2—C3	120.75 (11)	N10—C14—C5	118.62 (10)
O15—C2—C3	113.59 (10)	N10—C14—C13	123.13 (10)
C4—C3—C2	120.85 (11)	C5—C14—C13	118.25 (10)
C4—C3—H3	119.6	C2—O15—C16	117.61 (10)
C2—C3—H3	119.6	O15—C16—H16A	109.5
C3—C4—C12	121.32 (10)	O15—C16—H16B	109.5
C3—C4—H4	119.3	H16A—C16—H16B	109.5
C12—C4—H4	119.3	O15—C16—H16C	109.5
C6—C5—C14	120.86 (11)	H16A—C16—H16C	109.5
C6—C5—H5	119.6	H16B—C16—H16C	109.5
C14—C5—H5	119.6	C9—O17—C18	118.66 (7)
C5—C6—C7	120.77 (11)	C19—C18—C23	121.24 (9)
C5—C6—H6	119.6	C19—C18—O17	123.59 (9)
C7—C6—H6	119.6	C23—C18—O17	115.17 (9)
C8—C7—C6	120.77 (12)	C18—C19—C20	118.57 (10)
C8—C7—H7	119.6	C18—C19—H19	120.7
C6—C7—H7	119.6	C20—C19—H19	120.7
C7—C8—C13	120.35 (11)	C21—C20—C19	120.86 (11)
C7—C8—H8	119.8	C21—C20—H20	119.6
C13—C8—H8	119.8	C19—C20—H20	119.6
O17—C9—C13	119.33 (9)	C20—C21—C22	119.58 (11)
O17—C9—C11	118.88 (9)	C20—C21—H21	120.2
C13—C9—C11	121.64 (9)	C22—C21—H21	120.2
C12—N10—C14	118.10 (9)	C23—C22—C21	120.40 (10)
C9—C11—C1	123.79 (9)	C23—C22—H22	119.8
C9—C11—C12	116.22 (9)	C21—C22—H22	119.8
C1—C11—C12	119.99 (9)	C22—C23—C18	119.31 (10)
N10—C12—C4	118.53 (9)	C22—C23—H23	120.3
N10—C12—C11	123.94 (10)	C18—C23—H23	120.3

C11—C1—C2—O15	−178.96 (10)	C11—C9—C13—C14	1.82 (14)
C11—C1—C2—C3	0.15 (17)	C7—C8—C13—C9	−179.10 (10)
C1—C2—C3—C4	−0.73 (19)	C7—C8—C13—C14	0.59 (16)
O15—C2—C3—C4	178.49 (11)	C12—N10—C14—C5	179.97 (9)
C2—C3—C4—C12	0.68 (19)	C12—N10—C14—C13	−0.39 (15)
C14—C5—C6—C7	−0.13 (19)	C6—C5—C14—N10	−179.41 (11)
C5—C6—C7—C8	−0.47 (19)	C6—C5—C14—C13	0.93 (17)
C6—C7—C8—C13	0.22 (18)	C9—C13—C14—N10	−1.08 (14)
O17—C9—C11—C1	−5.34 (14)	C8—C13—C14—N10	179.21 (9)
C13—C9—C11—C1	179.14 (9)	C9—C13—C14—C5	178.57 (9)
O17—C9—C11—C12	174.41 (8)	C8—C13—C14—C5	−1.14 (14)
C13—C9—C11—C12	−1.11 (14)	C1—C2—O15—C16	3.06 (18)
C2—C1—C11—C9	−179.81 (10)	C3—C2—O15—C16	−176.11 (12)
C2—C1—C11—C12	0.45 (15)	C13—C9—O17—C18	−88.82 (11)
C14—N10—C12—C4	−179.03 (10)	C11—C9—O17—C18	95.56 (11)
C14—N10—C12—C11	1.18 (15)	C9—O17—C18—C19	4.98 (14)
C3—C4—C12—N10	−179.88 (11)	C9—O17—C18—C23	−175.51 (9)
C3—C4—C12—C11	−0.07 (17)	C23—C18—C19—C20	1.71 (16)
C9—C11—C12—N10	−0.46 (15)	O17—C18—C19—C20	−178.82 (9)
C1—C11—C12—N10	179.31 (10)	C18—C19—C20—C21	−0.10 (17)
C9—C11—C12—C4	179.75 (9)	C19—C20—C21—C22	−0.95 (19)
C1—C11—C12—C4	−0.49 (15)	C20—C21—C22—C23	0.4 (2)
O17—C9—C13—C8	6.01 (15)	C21—C22—C23—C18	1.14 (18)
C11—C9—C13—C8	−178.49 (9)	C19—C18—C23—C22	−2.23 (16)
O17—C9—C13—C14	−173.68 (8)	O17—C18—C23—C22	178.25 (10)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg4 are the centroids of the C1–C4/C11/C12 and C18–C23 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···N10ⁱ	0.93	2.60	3.487 (2)	160
C6—H6···Cg4ⁱⁱ	0.93	2.80	3.459 (2)	129
C16—H16B···Cg4ⁱⁱⁱ	0.96	2.94	3.658 (2)	133
C20—H20···Cg2^iv	0.93	2.71	3.576 (2)	156

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅NO₂
M_r	301.33
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	8.3042 (2), 15.5101 (4), 24.0192 (6)
V (Å³)	3093.65 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.25 × 0.10

Data collection
Diffractometer	Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.890, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	56825, 2747, 2322
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.086, 1.10
No. of reflections	2747
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.11

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).