2-(Acridin-9-yl­imino)-3-di­methyl­amino-1,3-thia­zolidin-4-one

In the title compound, C₁₈H₁₆N₄OS, prepared by the reaction of 4-(acridin-9-yl)-1,1-di­methyl­thio­semicarbazide with methyl bromo­acetate, the acridine and thia­zolidine ring systems are both non-planar and, because of steric requirements, almost perpendicular, with a dihedral angle between their planes of 99.69 (6)°. C—H...O and C—H...π(arene) hydrogen bonds stabilize the crystal structure in the solid state.

S1. Comment

Thiazole derivates, particularly 1,3-thiazolidin-4-ones, have a broad spectrum of biological activity (Singh et al., 1998; Liu & Anthonsen, 2000). Our continuing interest in 9-substituted acridine compounds, which may possess anticancer, chemiluminescent and intercalating properties (Kristian et al., 1998; Klika et al., 2001; Bernát et al., 2004; Demeunynck et al., 2001), led us to the synthesis of new acridin-9-yl-thiosemicarbazides and thiazolidinone derivatives. Besides the synthetic goal of this work, a presumed synergism of biological effects of both heterocyclic skeletons was another interesting point to study.

To obtain the target compounds, the reaction of acridin-9-yl isothiocyanate, (I), with 1,1- and 1,2-disubstituted hydrazines was used to give intermediate thiosemicarbazides, which were further cyclized with bromoacetic acid ester or bromide to obtain products of type IV (Fig. 1), (Vilková et al., 2005). Because of the presence of four nucleophilic centres in thiosemicarbazides, at least six types of isomeric five-membered heterocyclic structures could possibly be formed from the terminal cyclization step and/or subsequent possible rearrangements of the Dimroth type. An NMR proof of these structures is questionable because of ambiguities in assignments of cross peaks from two-dimensional H,C-correlation and NOESY spectra. Hence we have determined the structure of the selected model compound (IV), obtained by the reaction of 1,1-dimethyl-4-(acridin-9-yl)-thiosemicarbazide, (II), with methyl bromoacetate. The preparation of the studied compound involved the alkylation of the thiosemicarbazide to afford 1,1-dimethyl-4-(acridin-9-yl)-S-methoxycarbonylmethylene- isothiosemicarbazide hydrobromide, (III), by the attachment of the S atom of the thiosemicarbazide to a bromomethylene C atom (see scheme below).

A search of the Cambridge Structural Database (release of August 2004; Allen, 2002) showed that the title compound is the first example of a compound in which both acridine and thiazole ring systems are linked by an imine N atom. On the other hand, three derivatives of N-(acridin-9-yl)-1,4-benzoquinone monoimines have been structurally characterized (Clark et al., 1993), and there are two entries containing an imino-1,3-thiazolidin-4-one ring (Deepthi et al., 2001).

The acridine and thiazoline ring systems in (IV) both deviate significantly from planarity. Atom C2 exhibits the highest deviation, of 0.050 (3) Å from the mean plane through the 14 atoms of the acridine ring system, while in the thiazolidine ring, atom C15 deviates most from the mean plane [0.079 (3) Å]. The geometric parameters for the acridine ring system are similar to those found in phenyl-(acridin-9-yl)-amine (Leardini et al., 1998). The N2—C14 bond in the imine group is clearly shorter than the C9—N2 bond, indicating the double-bond character of the former. Similar distances were found in N-(9-acridinyl)-2-methoxy-1,4-benzoquinone monoimine (Clark et al., 1993). Owing to steric effects, the ring systems linked by imine atom N2 are almost perpendicular; the angle between the mean planes through the rings is 99.69 (6)°. The geometric parameters in the 1,3-thiazolidin-4-one ring are normal (Deepthi et al., 2001).

The packing of the individual molecules in the solid state is governed by two intermolecular C—H···O hydrogen bonds (Table 2) and a C—H···π(arene) hydrogen bond. Pairs of molecules of (IV) are linked by C15—H15···O1ⁱ [symmetry code: (i) −x, 1 − y, −z] hydrogen bonds, forming a ring that can be described by graph-set descriptor R²₂(8) (Berstein et al., 1995); moreover, each O1 atom participates in a C5—H5···O1ⁱⁱ [symmetry code: (ii) 1 + x, 1/2 − y, 1/2 + z] hydrogen bond, linking pairs of molecules into deformed planes. Finally, the planes interact by C18—H18···π(arene) hydrogen bonds.

S2. Experimental

Single crystals of (IV) in the form of bright-yellow needles suitable for X-ray studies were prepared by the following procedure. To a solution of 1,1-dimethyl hydrazine (0.120 g, 2 mmol) in anhydrous tetrahydrofuran (5 ml) was added, dropwise, acridin-9-yl isothiocyanate, (I) (Mazagová et al., 1994) (0.473 g, 2 mmol), dissolved in anhydrous tetrahydrofurane (5 ml). The reaction mixture was stirred at room temperature until isothiocyanate disappeared (monitored by thin-layer chromatography, eluant cyclohexane/ethyl acetate, 3:1); a precipitate of 1,1-dimethyl-4-(acridin-9-yl)-thiosemicarbazide, (II), was filtered off, dried and recrystallized from methanol/diethyl ether. Yield 60%, m.p. 466–469 K. ₁H NMR (DMSO-d₆): δ 2.76 (s, 6H, 2 × CH₃), 7.50–8.25 (m, 8H, AcrH), 9.59 (br s, 1H, NH), 10.40 (br s, 1H, NH). To a suspension of thiosemicarbazide (II) (0.2 g, 0.67 mmol) in dry benzene (5 ml), methyl bromoacetate (0.103 g, 0.063 ml, 0.67 mmol) was slowly added. The solution was stirred at room temperature for 5 h, triethylamine (0.137 g, 0.188 ml, 1.35 mmol) was added, and stirring was continued for the next 2 h. The solution was filtered, the filtrate was evaporated and the residue was chromatographed using a column filled with silica gel (Merck 109385, 0.040–0.063 mm, 230–400 mesh, eluant ethyl acetate/cyclohexane, 4:1). To a saturated solution of crude (IV) in hot ethyl acetate, n-heptane was added to first turbidity and the product was left to crystallize for 2 h. Yield 31%, m.p. 475–477 K. ₁H NMR (DMSO-d₆): δ 3.16 (s, 6H, H-17,18), 3.93 (s, 2H, H-15), 7.53, 7.81, 8.00, 8.12 (m, 8H, AcrH); ₁₃C NMR: δ: 30.8 (C-15), 42.7 (C-17,18), 117.0 (C-10,13), 123.9, 125.0, 129.2, 130.4 (AcrCH), 148.9 (C-11,12), 150.4 (C-9), 155.0? (C-14), 169.3 (C-16).

S3. Refinement

H atoms were freely refined with isotropic displacement parameters [C—H = 0.927 (19)–0.99 (3) Å).

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Crystal Impact, 2000); software used to prepare material for publication: program (reference)?.

Figures

Fig. 1. A view of title compound, showing displacement ellipsoids at the 30% probability level.

2-(Acridin-9-ylimino)-3-dimethylamino-1,3-thiazolidin-4-one

Crystal data

C18H16N4OS	F(000) = 704
Mr = 336.42	Dx = 1.368 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 3118 reflections
a = 7.282 (5) Å	θ = 2.1–25.0°
b = 19.456 (5) Å	µ = 0.21 mm^−1
c = 11.954 (5) Å	T = 298 K
β = 105.326 (5)°	Prism, yellow
V = 1633.4 (14) Å^3	0.40 × 0.12 × 0.11 mm
Z = 4

Data collection

Bruker SMART 1000 diffractometer	2867 independent reflections
Radiation source: fine-focus sealed tube	1776 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 8.192 pixels/mm pixels mm^-1	θmax = 25.0°, θmin = 2.1°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker 1999)	k = −23→15
Tmin = 0.787, Tmax = 0.977	l = −14→13
8245 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	All H-atom parameters refined
wR(F^2) = 0.079	w = 1/[σ^2(Fo^2) + (0.0351P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.87	(Δ/σ)max < 0.001
2867 reflections	Δρmax = 0.17 e Å^−3
282 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0023 (5)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.30409 (8)	0.33825 (3)	0.10522 (5)	0.04651 (19)
O1	0.0638 (2)	0.46877 (7)	−0.13032 (13)	0.0483 (4)
N1	0.9133 (2)	0.19210 (9)	0.24539 (16)	0.0469 (5)
N2	0.5803 (2)	0.32560 (9)	−0.00933 (15)	0.0429 (5)
N3	0.3238 (2)	0.39793 (8)	−0.08672 (13)	0.0366 (4)
N4	0.3830 (2)	0.41895 (9)	−0.18407 (15)	0.0455 (5)
C1	0.8163 (3)	0.37932 (12)	0.2086 (2)	0.0454 (6)
H1	0.746 (3)	0.4113 (10)	0.1552 (19)	0.053 (7)*
C2	0.9333 (3)	0.40223 (14)	0.3084 (2)	0.0534 (6)
H2	0.937 (3)	0.4497 (11)	0.3278 (18)	0.054 (7)*
C3	1.0400 (4)	0.35528 (15)	0.3900 (2)	0.0590 (7)
H3	1.118 (3)	0.3742 (10)	0.4576 (18)	0.051 (7)*
C4	1.0306 (3)	0.28751 (14)	0.3688 (2)	0.0545 (7)
H4	1.101 (3)	0.2557 (11)	0.4238 (18)	0.053 (6)*
C5	0.8044 (3)	0.09588 (12)	0.1220 (2)	0.0524 (6)
H5	0.880 (3)	0.0693 (10)	0.1806 (17)	0.043 (6)*
C6	0.6941 (4)	0.06853 (14)	0.0237 (2)	0.0577 (7)
H6	0.698 (3)	0.0202 (12)	0.013 (2)	0.071 (8)*
C7	0.5741 (4)	0.11024 (14)	−0.0614 (2)	0.0579 (7)
H7	0.500 (3)	0.0891 (11)	−0.132 (2)	0.071 (8)*
C8	0.5700 (3)	0.17908 (14)	−0.0456 (2)	0.0503 (6)
H8	0.490 (3)	0.2086 (10)	−0.1031 (19)	0.055 (7)*
C10	0.6839 (3)	0.21028 (11)	0.05681 (18)	0.0401 (5)
C11	0.8028 (3)	0.16762 (11)	0.14404 (19)	0.0425 (5)
C12	0.9123 (3)	0.26043 (11)	0.26361 (19)	0.0430 (5)
C13	0.8002 (3)	0.30799 (11)	0.18189 (18)	0.0382 (5)
C9	0.6831 (3)	0.28118 (11)	0.07814 (17)	0.0390 (5)
C14	0.4236 (3)	0.35167 (10)	−0.00316 (17)	0.0360 (5)
C15	0.1063 (3)	0.39156 (14)	0.0298 (2)	0.0475 (6)
H15A	0.084 (3)	0.4243 (10)	0.0830 (17)	0.049 (6)*
H15B	−0.002 (3)	0.3631 (12)	0.006 (2)	0.074 (8)*
C16	0.1567 (3)	0.42451 (11)	−0.07050 (18)	0.0375 (5)
C17	0.5622 (4)	0.45742 (17)	−0.1534 (3)	0.0620 (7)
H17A	0.672 (4)	0.4260 (14)	−0.124 (2)	0.104 (11)*
H17B	0.577 (3)	0.4775 (13)	−0.221 (2)	0.088 (9)*
H17C	0.555 (4)	0.4913 (14)	−0.096 (3)	0.101 (11)*
C18	0.3777 (4)	0.36265 (17)	−0.2658 (2)	0.0614 (8)
H18A	0.254 (4)	0.3391 (14)	−0.279 (2)	0.101 (10)*
H18B	0.396 (4)	0.3843 (13)	−0.332 (2)	0.089 (9)*
H18C	0.485 (3)	0.3316 (12)	−0.236 (2)	0.074 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0474 (3)	0.0548 (4)	0.0396 (3)	0.0042 (3)	0.0155 (3)	0.0075 (3)
O1	0.0462 (8)	0.0419 (9)	0.0533 (10)	0.0114 (8)	0.0070 (8)	0.0025 (8)
N1	0.0419 (10)	0.0473 (12)	0.0483 (12)	0.0060 (9)	0.0062 (10)	0.0068 (9)
N2	0.0399 (10)	0.0490 (11)	0.0394 (11)	0.0099 (9)	0.0100 (9)	0.0082 (8)
N3	0.0349 (9)	0.0414 (10)	0.0344 (10)	0.0050 (8)	0.0107 (8)	0.0058 (8)
N4	0.0438 (10)	0.0550 (12)	0.0395 (11)	0.0016 (9)	0.0141 (9)	0.0091 (9)
C1	0.0446 (13)	0.0468 (16)	0.0451 (15)	0.0034 (12)	0.0122 (12)	0.0079 (12)
C2	0.0570 (15)	0.0489 (17)	0.0545 (17)	−0.0058 (13)	0.0151 (14)	−0.0017 (13)
C3	0.0520 (15)	0.067 (2)	0.0509 (17)	−0.0079 (14)	0.0012 (13)	−0.0029 (14)
C4	0.0495 (15)	0.0572 (18)	0.0472 (16)	0.0059 (13)	−0.0038 (12)	0.0094 (13)
C5	0.0519 (15)	0.0474 (17)	0.0562 (18)	0.0094 (13)	0.0115 (14)	0.0080 (14)
C6	0.0627 (16)	0.0482 (17)	0.0639 (19)	0.0026 (14)	0.0198 (15)	−0.0017 (14)
C7	0.0568 (16)	0.0616 (19)	0.0530 (17)	−0.0028 (14)	0.0108 (14)	−0.0090 (14)
C8	0.0422 (13)	0.0606 (18)	0.0462 (16)	0.0084 (12)	0.0084 (12)	0.0009 (13)
C10	0.0338 (11)	0.0462 (14)	0.0418 (14)	0.0048 (10)	0.0124 (11)	0.0047 (10)
C11	0.0368 (11)	0.0437 (14)	0.0492 (14)	0.0053 (11)	0.0150 (11)	0.0068 (11)
C12	0.0339 (11)	0.0503 (15)	0.0446 (14)	0.0020 (11)	0.0102 (10)	0.0070 (11)
C13	0.0325 (11)	0.0438 (14)	0.0399 (13)	0.0043 (10)	0.0126 (10)	0.0068 (10)
C9	0.0312 (11)	0.0480 (14)	0.0402 (13)	0.0068 (10)	0.0139 (10)	0.0095 (10)
C14	0.0368 (11)	0.0382 (13)	0.0320 (12)	0.0002 (10)	0.0073 (9)	−0.0001 (10)
C15	0.0454 (14)	0.0500 (16)	0.0504 (16)	0.0054 (13)	0.0185 (13)	0.0002 (12)
C16	0.0359 (11)	0.0361 (13)	0.0389 (13)	0.0000 (10)	0.0073 (10)	−0.0047 (10)
C17	0.0623 (18)	0.064 (2)	0.065 (2)	−0.0158 (16)	0.0255 (16)	0.0042 (16)
C18	0.0565 (18)	0.089 (2)	0.0413 (16)	−0.0088 (17)	0.0165 (14)	−0.0089 (15)

Geometric parameters (Å, º)

S1—C14	1.761 (2)	C5—C11	1.421 (3)
S1—C15	1.810 (2)	C5—H5	0.927 (19)
O1—C16	1.206 (2)	C6—C7	1.410 (3)
N1—C12	1.347 (2)	C6—H6	0.95 (2)
N1—C11	1.352 (3)	C7—C8	1.354 (3)
N2—C14	1.269 (2)	C7—H7	0.97 (2)
N2—C9	1.409 (2)	C8—C10	1.421 (3)
N3—C16	1.383 (2)	C8—H8	0.96 (2)
N3—C14	1.397 (2)	C10—C9	1.403 (3)
N3—N4	1.404 (2)	C10—C11	1.431 (3)
N4—C18	1.461 (3)	C12—C13	1.434 (3)
N4—C17	1.465 (3)	C13—C9	1.407 (3)
C1—C2	1.346 (3)	C15—C16	1.488 (3)
C1—C13	1.422 (3)	C15—H15A	0.94 (2)
C1—H1	0.94 (2)	C15—H15B	0.94 (2)
C2—C3	1.410 (3)	C17—H17A	0.99 (3)
C2—H2	0.95 (2)	C17—H17B	0.93 (3)
C3—C4	1.341 (3)	C17—H17C	0.96 (3)
C3—H3	0.93 (2)	C18—H18A	0.99 (3)
C4—C12	1.424 (3)	C18—H18B	0.94 (3)
C4—H4	0.95 (2)	C18—H18C	0.98 (2)
C5—C6	1.345 (3)
C14—S1—C15	91.81 (11)	N1—C11—C5	118.7 (2)
C12—N1—C11	117.71 (18)	N1—C11—C10	123.4 (2)
C14—N2—C9	120.77 (17)	C5—C11—C10	117.9 (2)
C16—N3—C14	116.84 (17)	N1—C12—C4	118.7 (2)
C16—N3—N4	118.78 (16)	N1—C12—C13	123.6 (2)
C14—N3—N4	124.38 (16)	C4—C12—C13	117.7 (2)
N3—N4—C18	112.08 (18)	C9—C13—C1	123.70 (19)
N3—N4—C17	112.91 (19)	C9—C13—C12	117.69 (19)
C18—N4—C17	114.5 (2)	C1—C13—C12	118.6 (2)
C2—C1—C13	121.2 (2)	C10—C9—C13	119.62 (19)
C2—C1—H1	119.1 (13)	C10—C9—N2	119.67 (19)
C13—C1—H1	119.7 (13)	C13—C9—N2	120.40 (19)
C1—C2—C3	120.2 (3)	N2—C14—N3	121.46 (18)
C1—C2—H2	120.5 (13)	N2—C14—S1	127.64 (16)
C3—C2—H2	119.1 (13)	N3—C14—S1	110.90 (14)
C4—C3—C2	121.0 (3)	C16—C15—S1	108.36 (16)
C4—C3—H3	122.7 (13)	C16—C15—H15A	112.0 (12)
C2—C3—H3	116.3 (13)	S1—C15—H15A	107.8 (12)
C3—C4—C12	121.3 (2)	C16—C15—H15B	111.7 (15)
C3—C4—H4	121.2 (13)	S1—C15—H15B	107.8 (14)
C12—C4—H4	117.4 (13)	H15A—C15—H15B	109.0 (19)
C6—C5—C11	121.2 (2)	O1—C16—N3	124.10 (19)
C6—C5—H5	122.7 (12)	O1—C16—C15	124.47 (19)
C11—C5—H5	116.1 (12)	N3—C16—C15	111.43 (18)
C5—C6—C7	121.0 (3)	N4—C17—H17A	110.8 (15)
C5—C6—H6	118.8 (15)	N4—C17—H17B	107.5 (16)
C7—C6—H6	120.2 (15)	H17A—C17—H17B	107 (2)
C8—C7—C6	120.1 (3)	N4—C17—H17C	108.3 (16)
C8—C7—H7	121.0 (14)	H17A—C17—H17C	111 (2)
C6—C7—H7	118.9 (14)	H17B—C17—H17C	112 (2)
C7—C8—C10	120.9 (2)	N4—C18—H18A	108.2 (16)
C7—C8—H8	121.4 (12)	N4—C18—H18B	104.1 (16)
C10—C8—H8	117.7 (12)	H18A—C18—H18B	114 (2)
C9—C10—C8	123.2 (2)	N4—C18—H18C	110.1 (14)
C9—C10—C11	117.9 (2)	H18A—C18—H18C	112 (2)
C8—C10—C11	118.9 (2)	H18B—C18—H18C	108 (2)
C16—N3—N4—C18	−113.6 (2)	N1—C12—C13—C1	−177.58 (19)
C14—N3—N4—C18	66.9 (3)	C4—C12—C13—C1	1.5 (3)
C16—N3—N4—C17	115.3 (2)	C8—C10—C9—C13	179.95 (18)
C14—N3—N4—C17	−64.2 (3)	C11—C10—C9—C13	1.3 (3)
C13—C1—C2—C3	−1.3 (3)	C8—C10—C9—N2	−6.5 (3)
C1—C2—C3—C4	1.6 (4)	C11—C10—C9—N2	174.81 (16)
C2—C3—C4—C12	−0.2 (4)	C1—C13—C9—C10	176.76 (19)
C11—C5—C6—C7	0.5 (4)	C12—C13—C9—C10	−1.8 (3)
C5—C6—C7—C8	0.7 (4)	C1—C13—C9—N2	3.3 (3)
C6—C7—C8—C10	−0.7 (4)	C12—C13—C9—N2	−175.31 (17)
C7—C8—C10—C9	−179.2 (2)	C14—N2—C9—C10	105.3 (2)
C7—C8—C10—C11	−0.5 (3)	C14—N2—C9—C13	−81.2 (2)
C12—N1—C11—C5	178.82 (18)	C9—N2—C14—N3	177.41 (18)
C12—N1—C11—C10	−0.9 (3)	C9—N2—C14—S1	−1.5 (3)
C6—C5—C11—N1	178.6 (2)	C16—N3—C14—N2	−178.60 (18)
C6—C5—C11—C10	−1.7 (3)	N4—N3—C14—N2	1.0 (3)
C9—C10—C11—N1	0.1 (3)	C16—N3—C14—S1	0.5 (2)
C8—C10—C11—N1	−178.61 (19)	N4—N3—C14—S1	−179.95 (14)
C9—C10—C11—C5	−179.59 (18)	C15—S1—C14—N2	−177.0 (2)
C8—C10—C11—C5	1.7 (3)	C15—S1—C14—N3	4.03 (16)
C11—N1—C12—C4	−178.78 (19)	C14—S1—C15—C16	−7.05 (18)
C11—N1—C12—C13	0.3 (3)	C14—N3—C16—O1	174.02 (19)
C3—C4—C12—N1	177.8 (2)	N4—N3—C16—O1	−5.6 (3)
C3—C4—C12—C13	−1.3 (3)	C14—N3—C16—C15	−6.0 (2)
C2—C1—C13—C9	−178.8 (2)	N4—N3—C16—C15	174.34 (18)
C2—C1—C13—C12	−0.2 (3)	S1—C15—C16—O1	−171.51 (17)
N1—C12—C13—C9	1.1 (3)	S1—C15—C16—N3	8.5 (2)
C4—C12—C13—C9	−179.86 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1^i	0.93 (2)	2.42 (2)	3.311 (4)	161.7 (17)
C15—H15A···O1^ii	0.94 (2)	2.48 (2)	3.339 (4)	152.1 (16)
C18—H18B···Cg^iii	0.94 (3)	2.97 (3)	3.645 (4)	131 (2)

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