2-(4-Chloro-phen-yl)-1,5-diphenyl-3-tosyl-imidazolidin-4-one.

In the title compound, C(28)H(23)ClN(2)O(3)S, the central imidazolidine ring adopts a twisted conformation and the S atom has distorted tetra-hedral geometry. The crystal packing is stabilized by C-H⋯O, C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.8302 (10) Å].

Related literature

For the biological activity of sulfonamides, see: Zareef et al. (2007 ▶); Chohan et al. (2007 ▶); Pomarnacka & Kozlarska-Kedra (2003 ▶); Nieto et al. (2005 ▶); Wang et al. (1995 ▶). For a related structure, see: Chakkaravarthi et al. (2008 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli et al. (1983 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C28H23ClN2O3S

M = 503.00

Monoclinic,

a = 10.8458 (3) Å

b = 13.0191 (4) Å

c = 17.6720 (5) Å

β = 103.757 (2)°

V = 2423.75 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 293 K

0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.981, T max = 0.985

32315 measured reflections

7313 independent reflections

5098 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.115

S = 1.05

7313 reflections

317 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008427/pk2300sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008427/pk2300Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C28H23ClN2O3S	F(000) = 1048
Mr = 503.00	Dx = 1.378 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7313 reflections
a = 10.8458 (3) Å	θ = 2.4–30.4°
b = 13.0191 (4) Å	µ = 0.28 mm−1
c = 17.6720 (5) Å	T = 293 K
β = 103.757 (2)°	Block, colourless
V = 2423.75 (12) Å3	0.25 × 0.22 × 0.19 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	7313 independent reflections
Radiation source: fine-focus sealed tube	5098 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω and φ scans	θmax = 30.4°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.981, Tmax = 0.985	k = −17→18
32315 measured reflections	l = −22→25

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0495P)2 + 0.5408P] where P = (Fo2 + 2Fc2)/3
7313 reflections	(Δ/σ)max = 0.001
317 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.8204 (2)	0.6211 (2)	−0.10561 (13)	0.0944 (10)
H1A	0.8293	0.5757	−0.1468	0.142*
H1B	0.8843	0.6735	−0.0987	0.142*
H1C	0.7378	0.6523	−0.1188	0.142*
C2	0.83550 (16)	0.5610 (2)	−0.03116 (10)	0.0615 (6)
C3	0.87311 (18)	0.60888 (16)	0.03995 (11)	0.0592 (5)
H3	0.8903	0.6789	0.0417	0.071*
C4	0.88600 (16)	0.55548 (13)	0.10884 (10)	0.0477 (4)
H4	0.9107	0.5892	0.1565	0.057*
C5	0.86169 (13)	0.45127 (12)	0.10598 (8)	0.0370 (3)
C6	0.82418 (16)	0.40127 (16)	0.03542 (10)	0.0524 (4)
H6	0.8079	0.3311	0.0334	0.063*
C7	0.81134 (17)	0.4579 (2)	−0.03242 (10)	0.0649 (6)
H7	0.7855	0.4248	−0.0802	0.078*
C8	0.65428 (12)	0.31035 (10)	0.20980 (7)	0.0301 (3)
H8	0.6929	0.2445	0.2291	0.036*
C9	0.58939 (12)	0.30175 (10)	0.12399 (8)	0.0298 (3)
C10	0.51246 (13)	0.37975 (11)	0.08615 (8)	0.0359 (3)
H10	0.4942	0.4355	0.1145	0.043*
C11	0.46242 (14)	0.37599 (12)	0.00672 (9)	0.0396 (3)
H11	0.4102	0.4284	−0.0184	0.048*
C12	0.49087 (14)	0.29372 (12)	−0.03472 (8)	0.0398 (3)
C13	0.56268 (16)	0.21323 (13)	0.00174 (9)	0.0455 (4)
H13	0.5782	0.1566	−0.0268	0.055*
C14	0.61182 (14)	0.21732 (11)	0.08156 (9)	0.0389 (3)
H14	0.6602	0.1629	0.1068	0.047*
C15	0.46241 (13)	0.29610 (11)	0.26339 (8)	0.0336 (3)
C16	0.43733 (14)	0.19730 (12)	0.23351 (9)	0.0388 (3)
H16	0.4952	0.1644	0.2104	0.047*
C17	0.32626 (16)	0.14799 (14)	0.23816 (10)	0.0491 (4)
H17	0.3105	0.0818	0.2185	0.059*
C18	0.23885 (16)	0.19555 (16)	0.27141 (11)	0.0551 (5)
H18	0.1638	0.1623	0.2735	0.066*
C19	0.26360 (15)	0.29236 (15)	0.30142 (10)	0.0516 (4)
H19	0.2050	0.3246	0.3242	0.062*
C20	0.37404 (14)	0.34271 (13)	0.29837 (9)	0.0429 (3)
H20	0.3898	0.4081	0.3197	0.052*
C21	0.60120 (14)	0.45092 (11)	0.28719 (8)	0.0353 (3)
H21	0.5306	0.4961	0.2630	0.042*
C23	0.63258 (14)	0.46406 (11)	0.37521 (8)	0.0364 (3)
C28	0.70564 (19)	0.39176 (15)	0.42268 (10)	0.0578 (5)
H28	0.7302	0.3321	0.4013	0.069*
C27	0.7424 (2)	0.40811 (19)	0.50230 (11)	0.0731 (6)
H27	0.7914	0.3593	0.5344	0.088*
C26	0.7067 (2)	0.49587 (19)	0.53377 (11)	0.0694 (6)
H26	0.7324	0.5070	0.5872	0.083*
C25	0.6339 (2)	0.56698 (16)	0.48732 (11)	0.0628 (5)
H25	0.6089	0.6261	0.5092	0.075*
C24	0.59660 (18)	0.55168 (13)	0.40753 (10)	0.0491 (4)
H24	0.5472	0.6007	0.3759	0.059*
N1	0.75179 (11)	0.39178 (9)	0.22299 (6)	0.0318 (2)
N2	0.57393 (11)	0.34697 (10)	0.25969 (7)	0.0368 (3)
O1	0.98232 (10)	0.43180 (9)	0.25004 (6)	0.0459 (3)
O2	0.89588 (10)	0.27584 (9)	0.17703 (7)	0.0479 (3)
C22	0.71777 (14)	0.47825 (11)	0.25818 (8)	0.0350 (3)
S1	0.88693 (3)	0.38196 (3)	0.19302 (2)	0.03485 (10)
Cl1	0.43640 (5)	0.29404 (4)	−0.13549 (2)	0.06360 (15)
O3	0.77172 (11)	0.55951 (8)	0.26593 (7)	0.0480 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0684 (13)	0.165 (3)	0.0561 (13)	0.0392 (16)	0.0268 (11)	0.0549 (15)
C2	0.0390 (9)	0.1076 (17)	0.0414 (10)	0.0192 (10)	0.0163 (7)	0.0250 (10)
C3	0.0596 (11)	0.0658 (12)	0.0559 (11)	0.0111 (9)	0.0209 (9)	0.0236 (9)
C4	0.0540 (9)	0.0509 (9)	0.0390 (8)	−0.0006 (8)	0.0131 (7)	0.0051 (7)
C5	0.0329 (7)	0.0504 (9)	0.0292 (7)	−0.0002 (6)	0.0099 (5)	0.0016 (6)
C6	0.0496 (9)	0.0714 (12)	0.0382 (8)	−0.0063 (8)	0.0148 (7)	−0.0099 (8)
C7	0.0507 (10)	0.1166 (19)	0.0283 (8)	0.0025 (11)	0.0110 (7)	−0.0052 (10)
C8	0.0323 (6)	0.0316 (7)	0.0269 (6)	−0.0013 (5)	0.0078 (5)	−0.0011 (5)
C9	0.0304 (6)	0.0323 (7)	0.0273 (6)	−0.0012 (5)	0.0081 (5)	−0.0016 (5)
C10	0.0387 (7)	0.0351 (7)	0.0338 (7)	0.0041 (6)	0.0087 (6)	−0.0029 (6)
C11	0.0372 (7)	0.0431 (8)	0.0359 (7)	0.0017 (6)	0.0033 (6)	0.0054 (6)
C12	0.0383 (7)	0.0527 (9)	0.0267 (7)	−0.0074 (7)	0.0041 (6)	−0.0027 (6)
C13	0.0533 (9)	0.0458 (9)	0.0369 (8)	0.0005 (7)	0.0097 (7)	−0.0129 (7)
C14	0.0440 (8)	0.0370 (8)	0.0343 (7)	0.0054 (6)	0.0067 (6)	−0.0031 (6)
C15	0.0331 (7)	0.0423 (8)	0.0247 (6)	−0.0014 (6)	0.0057 (5)	0.0036 (5)
C16	0.0390 (7)	0.0424 (8)	0.0338 (7)	−0.0032 (6)	0.0067 (6)	0.0011 (6)
C17	0.0489 (9)	0.0514 (9)	0.0452 (9)	−0.0129 (8)	0.0076 (7)	0.0015 (7)
C18	0.0379 (8)	0.0745 (13)	0.0525 (10)	−0.0143 (8)	0.0098 (7)	0.0071 (9)
C19	0.0374 (8)	0.0731 (12)	0.0467 (9)	0.0013 (8)	0.0149 (7)	0.0025 (8)
C20	0.0408 (8)	0.0524 (9)	0.0372 (8)	0.0006 (7)	0.0123 (6)	−0.0024 (7)
C21	0.0404 (7)	0.0353 (7)	0.0313 (7)	0.0007 (6)	0.0106 (6)	−0.0028 (6)
C23	0.0420 (7)	0.0387 (7)	0.0314 (7)	−0.0048 (6)	0.0144 (6)	−0.0054 (6)
C28	0.0711 (12)	0.0630 (11)	0.0390 (9)	0.0181 (9)	0.0122 (8)	−0.0029 (8)
C27	0.0816 (14)	0.0961 (16)	0.0380 (10)	0.0180 (13)	0.0067 (10)	0.0061 (10)
C26	0.0871 (15)	0.0886 (15)	0.0351 (9)	−0.0171 (12)	0.0198 (10)	−0.0148 (10)
C25	0.0907 (14)	0.0578 (11)	0.0477 (10)	−0.0143 (11)	0.0320 (10)	−0.0208 (9)
C24	0.0671 (11)	0.0402 (8)	0.0462 (9)	−0.0046 (8)	0.0255 (8)	−0.0058 (7)
N1	0.0336 (6)	0.0333 (6)	0.0298 (6)	−0.0039 (5)	0.0101 (5)	−0.0039 (5)
N2	0.0402 (6)	0.0400 (6)	0.0341 (6)	−0.0072 (5)	0.0165 (5)	−0.0096 (5)
O1	0.0361 (5)	0.0592 (7)	0.0382 (6)	−0.0085 (5)	0.0003 (4)	0.0051 (5)
O2	0.0454 (6)	0.0413 (6)	0.0606 (7)	0.0060 (5)	0.0200 (6)	−0.0006 (5)
C22	0.0427 (7)	0.0357 (7)	0.0269 (6)	−0.0005 (6)	0.0088 (6)	−0.0004 (5)
S1	0.03133 (17)	0.0400 (2)	0.03336 (18)	0.00022 (14)	0.00796 (13)	0.00157 (14)
Cl1	0.0700 (3)	0.0859 (4)	0.02902 (19)	−0.0131 (3)	0.00031 (19)	−0.0035 (2)
O3	0.0615 (7)	0.0359 (6)	0.0511 (7)	−0.0115 (5)	0.0225 (6)	−0.0069 (5)

C1—C2	1.506 (3)	C15—N2	1.3941 (18)
C1—H1A	0.9600	C15—C20	1.397 (2)
C1—H1B	0.9600	C16—C17	1.385 (2)
C1—H1C	0.9600	C16—H16	0.9300
C2—C7	1.366 (3)	C17—C18	1.376 (3)
C2—C3	1.375 (3)	C17—H17	0.9300
C3—C4	1.380 (2)	C18—C19	1.369 (3)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.381 (2)	C19—C20	1.378 (2)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.380 (2)	C20—H20	0.9300
C5—S1	1.7478 (15)	C21—N2	1.4446 (19)
C6—C7	1.386 (3)	C21—C22	1.5154 (19)
C6—H6	0.9300	C21—C23	1.5207 (19)
C7—H7	0.9300	C21—H21	0.9800
C8—N2	1.4592 (17)	C23—C24	1.373 (2)
C8—N1	1.4764 (17)	C23—C28	1.379 (2)
C8—C9	1.5165 (18)	C28—C27	1.385 (3)
C8—H8	0.9800	C28—H28	0.9300
C9—C10	1.3817 (19)	C27—C26	1.366 (3)
C9—C14	1.3844 (19)	C27—H27	0.9300
C10—C11	1.380 (2)	C26—C25	1.359 (3)
C10—H10	0.9300	C26—H26	0.9300
C11—C12	1.373 (2)	C25—C24	1.386 (2)
C11—H11	0.9300	C25—H25	0.9300
C12—C13	1.372 (2)	C24—H24	0.9300
C12—Cl1	1.7377 (15)	N1—C22	1.3782 (18)
C13—C14	1.385 (2)	N1—S1	1.6776 (11)
C13—H13	0.9300	O1—S1	1.4181 (11)
C14—H14	0.9300	O2—S1	1.4181 (12)
C15—C16	1.393 (2)	C22—O3	1.2008 (17)
C2—C1—H1A	109.5	C15—C16—H16	120.0
C2—C1—H1B	109.5	C18—C17—C16	120.95 (17)
H1A—C1—H1B	109.5	C18—C17—H17	119.5
C2—C1—H1C	109.5	C16—C17—H17	119.5
H1A—C1—H1C	109.5	C19—C18—C17	119.23 (16)
H1B—C1—H1C	109.5	C19—C18—H18	120.4
C7—C2—C3	118.31 (17)	C17—C18—H18	120.4
C7—C2—C1	121.0 (2)	C18—C19—C20	121.00 (16)
C3—C2—C1	120.7 (2)	C18—C19—H19	119.5
C2—C3—C4	121.58 (19)	C20—C19—H19	119.5
C2—C3—H3	119.2	C19—C20—C15	120.34 (16)
C4—C3—H3	119.2	C19—C20—H20	119.8
C3—C4—C5	118.97 (17)	C15—C20—H20	119.8
C3—C4—H4	120.5	N2—C21—C22	103.10 (11)
C5—C4—H4	120.5	N2—C21—C23	115.32 (12)
C6—C5—C4	120.63 (15)	C22—C21—C23	108.53 (11)
C6—C5—S1	120.18 (13)	N2—C21—H21	109.9
C4—C5—S1	119.11 (12)	C22—C21—H21	109.9
C5—C6—C7	118.55 (19)	C23—C21—H21	109.9
C5—C6—H6	120.7	C24—C23—C28	119.54 (15)
C7—C6—H6	120.7	C24—C23—C21	120.15 (14)
C2—C7—C6	121.95 (18)	C28—C23—C21	120.13 (13)
C2—C7—H7	119.0	C23—C28—C27	119.88 (17)
C6—C7—H7	119.0	C23—C28—H28	120.1
N2—C8—N1	100.27 (10)	C27—C28—H28	120.1
N2—C8—C9	115.24 (11)	C26—C27—C28	120.1 (2)
N1—C8—C9	110.82 (10)	C26—C27—H27	120.0
N2—C8—H8	110.0	C28—C27—H27	120.0
N1—C8—H8	110.0	C25—C26—C27	120.27 (18)
C9—C8—H8	110.0	C25—C26—H26	119.9
C10—C9—C14	119.01 (13)	C27—C26—H26	119.9
C10—C9—C8	120.87 (12)	C26—C25—C24	120.25 (18)
C14—C9—C8	120.04 (12)	C26—C25—H25	119.9
C11—C10—C9	120.82 (13)	C24—C25—H25	119.9
C11—C10—H10	119.6	C23—C24—C25	119.98 (18)
C9—C10—H10	119.6	C23—C24—H24	120.0
C12—C11—C10	119.08 (14)	C25—C24—H24	120.0
C12—C11—H11	120.5	C22—N1—C8	113.53 (11)
C10—C11—H11	120.5	C22—N1—S1	123.54 (9)
C13—C12—C11	121.32 (14)	C8—N1—S1	122.84 (9)
C13—C12—Cl1	120.00 (12)	C15—N2—C21	122.66 (12)
C11—C12—Cl1	118.67 (12)	C15—N2—C8	121.51 (11)
C12—C13—C14	119.14 (14)	C21—N2—C8	113.92 (11)
C12—C13—H13	120.4	O3—C22—N1	126.55 (13)
C14—C13—H13	120.4	O3—C22—C21	126.26 (13)
C9—C14—C13	120.49 (14)	N1—C22—C21	107.17 (11)
C9—C14—H14	119.8	O1—S1—O2	120.96 (7)
C13—C14—H14	119.8	O1—S1—N1	106.58 (6)
C16—C15—N2	120.96 (13)	O2—S1—N1	104.10 (6)
C16—C15—C20	118.45 (14)	O1—S1—C5	108.92 (7)
N2—C15—C20	120.58 (14)	O2—S1—C5	109.35 (7)
C17—C16—C15	120.01 (15)	N1—S1—C5	105.82 (6)
C17—C16—H16	120.0
C7—C2—C3—C4	−0.3 (3)	C27—C26—C25—C24	−0.8 (3)
C1—C2—C3—C4	179.17 (17)	C28—C23—C24—C25	0.1 (3)
C2—C3—C4—C5	0.7 (3)	C21—C23—C24—C25	−174.97 (15)
C3—C4—C5—C6	−0.5 (2)	C26—C25—C24—C23	0.4 (3)
C3—C4—C5—S1	176.25 (13)	N2—C8—N1—C22	−14.57 (14)
C4—C5—C6—C7	−0.1 (2)	C9—C8—N1—C22	107.61 (13)
S1—C5—C6—C7	−176.75 (13)	N2—C8—N1—S1	168.83 (9)
C3—C2—C7—C6	−0.2 (3)	C9—C8—N1—S1	−69.00 (14)
C1—C2—C7—C6	−179.74 (17)	C16—C15—N2—C21	177.49 (13)
C5—C6—C7—C2	0.4 (3)	C20—C15—N2—C21	−3.5 (2)
N2—C8—C9—C10	45.41 (17)	C16—C15—N2—C8	14.2 (2)
N1—C8—C9—C10	−67.56 (15)	C20—C15—N2—C8	−166.84 (13)
N2—C8—C9—C14	−137.83 (13)	C22—C21—N2—C15	−170.26 (12)
N1—C8—C9—C14	109.21 (14)	C23—C21—N2—C15	71.64 (17)
C14—C9—C10—C11	−2.5 (2)	C22—C21—N2—C8	−5.78 (16)
C8—C9—C10—C11	174.27 (13)	C23—C21—N2—C8	−123.89 (13)
C9—C10—C11—C12	−0.5 (2)	N1—C8—N2—C15	176.67 (12)
C10—C11—C12—C13	3.2 (2)	C9—C8—N2—C15	57.67 (17)
C10—C11—C12—Cl1	−175.62 (11)	N1—C8—N2—C21	11.99 (15)
C11—C12—C13—C14	−2.8 (2)	C9—C8—N2—C21	−107.01 (14)
Cl1—C12—C13—C14	176.03 (12)	C8—N1—C22—O3	−169.50 (14)
C10—C9—C14—C13	2.9 (2)	S1—N1—C22—O3	7.1 (2)
C8—C9—C14—C13	−173.88 (13)	C8—N1—C22—C21	11.90 (15)
C12—C13—C14—C9	−0.3 (2)	S1—N1—C22—C21	−171.52 (9)
N2—C15—C16—C17	179.67 (14)	N2—C21—C22—O3	177.75 (14)
C20—C15—C16—C17	0.7 (2)	C23—C21—C22—O3	−59.49 (19)
C15—C16—C17—C18	0.6 (2)	N2—C21—C22—N1	−3.64 (15)
C16—C17—C18—C19	−1.1 (3)	C23—C21—C22—N1	119.12 (13)
C17—C18—C19—C20	0.4 (3)	C22—N1—S1—O1	38.67 (13)
C18—C19—C20—C15	0.9 (3)	C8—N1—S1—O1	−145.07 (10)
C16—C15—C20—C19	−1.4 (2)	C22—N1—S1—O2	167.58 (11)
N2—C15—C20—C19	179.58 (14)	C8—N1—S1—O2	−16.15 (12)
N2—C21—C23—C24	−145.95 (14)	C22—N1—S1—C5	−77.18 (12)
C22—C21—C23—C24	99.02 (16)	C8—N1—S1—C5	99.08 (11)
N2—C21—C23—C28	39.0 (2)	C6—C5—S1—O1	149.38 (12)
C22—C21—C23—C28	−76.01 (18)	C4—C5—S1—O1	−27.35 (14)
C24—C23—C28—C27	−0.2 (3)	C6—C5—S1—O2	15.21 (14)
C21—C23—C28—C27	174.86 (17)	C4—C5—S1—O2	−161.53 (12)
C23—C28—C27—C26	−0.2 (3)	C6—C5—S1—N1	−96.37 (13)
C28—C27—C26—C25	0.7 (4)	C4—C5—S1—N1	86.89 (13)

Cg2 and Cg4 are the centroids of the C2–C7 and C15–C20 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2	0.93	2.59	2.934 (2)	102
C8—H8···O3i	0.98	2.44	3.3659 (17)	158
C14—H14···O3i	0.93	2.57	3.3855 (19)	146
C24—H24···O2ii	0.93	2.59	3.289 (2)	132
C1—H1C···Cg4iii	0.96	2.90	3.484 (2)	120
C11—H11···Cg2iii	0.93	2.88	3.619 (17)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of the C2–C7 and C15–C20 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O3i	0.98	2.44	3.3659 (17)	158
C14—H14⋯O3i	0.93	2.57	3.3855 (19)	146
C24—H24⋯O2ii	0.93	2.59	3.289 (2)	132
C1—H1C⋯Cg4iii	0.96	2.90	3.484 (2)	120
C11—H11⋯Cg2iii	0.93	2.88	3.619 (17)	138

Symmetry codes: (i) ; (ii) ; (iii) .