2,2'-[2,4-Bis(naphthalen-1-yl)cyclo-butane-1,3-di-yl]bis-(1-methyl-pyridinium) bis-(4-chloro-benzene-sulfonate): thermal-induced [2 + 2] cyclo-addition reaction of a heterostilbene.

The asymmetric unit of the title salt, C36H32N2 (2+)·2C6H4ClO3S(-), consists of one anion and one half-cation, the other half being generated by inversion symmetry. The dihedral angle between the pyridinium ring and the napthalene ring system in the asymmetric unit is 42.86 (6)°. In the crystal, cations and anions are linked by weak C-H⋯O inter-actions into chains along [010]. Adjacent chains are further arranged in an anti-parallel manner into sheets parallel to the bc plane. π-π inter-actions are observed involving the cations, with centroid-centroid distances of 3.7664 (8) and 3.8553 (8) Å.

Related literature

For background to stibene and [2 + 2] photodimerization, see: Chanawanno et al. (2010 ▶); Chantrapromma et al. (2007 ▶); Papaefsta­thiou et al. (2002 ▶); Ruanwas et al. (2010 ▶); Yayli et al. (2004 ▶); Zhang et al. (2013 ▶). For related structures, see: Chantrapromma et al. (2012 ▶); Fun, Chanawanno & Chantrapromma (2009 ▶); Fun, Surasit et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C36H32N2 2+·2C6H4ClO3S−

M = 875.86

Triclinic,

a = 7.5488 (3) Å

b = 11.1899 (4) Å

c = 12.3853 (5) Å

α = 79.904 (2)°

β = 75.964 (2)°

γ = 89.266 (2)°

V = 998.76 (7) Å3

Z = 1

Mo Kα radiation

μ = 0.32 mm−1

T = 100 K

0.56 × 0.50 × 0.21 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.837, T max = 0.936

35475 measured reflections

5817 independent reflections

4977 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.115

S = 1.09

5817 reflections

351 parameters

All H-atom parameters refined

Δρmax = 0.50 e Å−3

Δρmin = −0.74 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009 ▶), Mercury (Macrae et al., 2006 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681400645X/rz5110sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400645X/rz5110Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681400645X/rz5110Isup3.cml

CCDC reference: 993267

Additional supporting information: crystallographic information; 3D view; checkCIF report

C36H32N22+·2C6H4ClO3S−	Z = 1
Mr = 875.86	F(000) = 456
Triclinic, P1	Dx = 1.456 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5488 (3) Å	Cell parameters from 5817 reflections
b = 11.1899 (4) Å	θ = 1.9–30.0°
c = 12.3853 (5) Å	µ = 0.32 mm−1
α = 79.904 (2)°	T = 100 K
β = 75.964 (2)°	Plate, yellow
γ = 89.266 (2)°	0.56 × 0.50 × 0.21 mm
V = 998.76 (7) Å3

Bruker APEXII CCD area-detector diffractometer	5817 independent reflections
Radiation source: sealed tube	4977 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 30.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.837, Tmax = 0.936	k = −15→15
35475 measured reflections	l = −17→17

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	All H-atom parameters refined
S = 1.09	w = 1/[σ2(Fo2) + (0.052P)2 + 0.7427P] where P = (Fo2 + 2Fc2)/3
5817 reflections	(Δ/σ)max = 0.001
351 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.74 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	0.34039 (7)	0.25081 (7)	0.47197 (4)	0.05223 (17)
S1	0.78639 (5)	0.19952 (3)	0.84360 (3)	0.01743 (9)
O1	0.73608 (18)	0.08040 (9)	0.91361 (10)	0.0249 (2)
O2	0.73144 (17)	0.29857 (10)	0.90582 (9)	0.0247 (2)
O3	0.97566 (16)	0.21127 (10)	0.77961 (10)	0.0245 (2)
N1	0.71757 (16)	0.75327 (10)	0.97380 (10)	0.0141 (2)
C1	0.65583 (19)	0.21394 (13)	0.74055 (12)	0.0169 (2)
C2	0.6222 (2)	0.11222 (14)	0.69692 (13)	0.0216 (3)
H2	0.669 (3)	0.036 (2)	0.7248 (18)	0.030 (5)*
C3	0.5228 (2)	0.12351 (18)	0.61444 (14)	0.0295 (4)
H3	0.499 (4)	0.050 (2)	0.587 (2)	0.048 (7)*
C4	0.4605 (2)	0.23620 (19)	0.57678 (13)	0.0310 (4)
C5	0.4931 (2)	0.33809 (18)	0.61922 (14)	0.0306 (4)
H5	0.445 (4)	0.416 (2)	0.594 (2)	0.044 (7)*
C6	0.5919 (2)	0.32641 (15)	0.70183 (13)	0.0243 (3)
H6	0.614 (3)	0.399 (2)	0.733 (2)	0.043 (7)*
C7	1.1080 (2)	0.50647 (12)	0.73600 (12)	0.0171 (3)
H7	1.107 (3)	0.420 (2)	0.7661 (18)	0.031 (5)*
C8	1.0998 (2)	0.54409 (13)	0.62185 (12)	0.0201 (3)
H8	1.094 (3)	0.4832 (19)	0.5774 (17)	0.023 (5)*
C9	1.0930 (2)	0.66488 (14)	0.57787 (12)	0.0198 (3)
H9	1.083 (3)	0.692 (2)	0.498 (2)	0.037 (6)*
C10	1.09915 (19)	0.75385 (12)	0.64568 (11)	0.0166 (2)
C11	1.0880 (2)	0.87977 (13)	0.60332 (12)	0.0201 (3)
H11	1.079 (3)	0.9014 (19)	0.5266 (17)	0.025 (5)*
C12	1.0923 (2)	0.96528 (13)	0.66949 (13)	0.0214 (3)
H12	1.081 (3)	1.0496 (19)	0.6386 (17)	0.025 (5)*
C13	1.1119 (2)	0.92916 (12)	0.78099 (13)	0.0187 (3)
H13	1.113 (3)	0.9900 (19)	0.8269 (17)	0.024 (5)*
C14	1.12389 (19)	0.80819 (12)	0.82451 (12)	0.0156 (2)
H14	1.139 (3)	0.7860 (17)	0.9006 (16)	0.016 (4)*
C15	1.11430 (18)	0.71681 (12)	0.75936 (11)	0.0139 (2)
C16	1.11371 (18)	0.58955 (12)	0.80500 (11)	0.0136 (2)
C17	1.10424 (18)	0.55360 (11)	0.92961 (11)	0.0127 (2)
H17	1.208 (2)	0.5887 (16)	0.9483 (15)	0.013 (4)*
C18	0.92111 (18)	0.58354 (11)	1.01586 (11)	0.0128 (2)
H18	0.951 (3)	0.6318 (18)	1.0651 (17)	0.022 (5)*
C19	0.77448 (17)	0.63876 (11)	0.96192 (11)	0.0127 (2)
C20	0.70618 (18)	0.58062 (12)	0.88915 (12)	0.0154 (2)
H20	0.743 (3)	0.4980 (18)	0.8833 (17)	0.023 (5)*
C21	0.59784 (19)	0.64167 (13)	0.82278 (12)	0.0175 (3)
H21	0.552 (3)	0.6025 (19)	0.7721 (18)	0.027 (5)*
C22	0.5555 (2)	0.76146 (13)	0.83035 (13)	0.0187 (3)
H22	0.478 (3)	0.806 (2)	0.7852 (18)	0.028 (5)*
C23	0.61171 (19)	0.81340 (12)	0.90961 (12)	0.0174 (3)
H23	0.578 (3)	0.8907 (19)	0.9267 (17)	0.025 (5)*
C24	0.7691 (2)	0.81744 (13)	1.05723 (12)	0.0178 (3)
H24A	0.750 (3)	0.7626 (19)	1.1291 (17)	0.023 (5)*
H24B	0.694 (3)	0.886 (2)	1.0634 (18)	0.031 (6)*
H24C	0.895 (3)	0.8424 (19)	1.0323 (18)	0.027 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0367 (3)	0.0909 (5)	0.0291 (2)	−0.0113 (3)	−0.02130 (19)	0.0088 (2)
S1	0.02519 (18)	0.00977 (15)	0.02051 (17)	−0.00007 (12)	−0.01122 (13)	−0.00329 (11)
O1	0.0397 (6)	0.0112 (4)	0.0270 (5)	−0.0022 (4)	−0.0167 (5)	0.0003 (4)
O2	0.0404 (7)	0.0139 (5)	0.0229 (5)	−0.0003 (4)	−0.0111 (5)	−0.0072 (4)
O3	0.0231 (5)	0.0204 (5)	0.0343 (6)	0.0009 (4)	−0.0135 (5)	−0.0069 (4)
N1	0.0151 (5)	0.0097 (5)	0.0181 (5)	0.0009 (4)	−0.0051 (4)	−0.0023 (4)
C1	0.0177 (6)	0.0167 (6)	0.0171 (6)	0.0012 (5)	−0.0057 (5)	−0.0030 (5)
C2	0.0245 (7)	0.0209 (7)	0.0214 (7)	−0.0032 (5)	−0.0083 (5)	−0.0049 (5)
C3	0.0287 (8)	0.0401 (10)	0.0219 (7)	−0.0094 (7)	−0.0096 (6)	−0.0057 (7)
C4	0.0197 (7)	0.0538 (11)	0.0184 (7)	−0.0029 (7)	−0.0081 (6)	0.0016 (7)
C5	0.0262 (8)	0.0377 (9)	0.0245 (7)	0.0105 (7)	−0.0072 (6)	0.0040 (7)
C6	0.0284 (8)	0.0219 (7)	0.0224 (7)	0.0073 (6)	−0.0073 (6)	−0.0021 (6)
C7	0.0210 (6)	0.0130 (6)	0.0174 (6)	0.0022 (5)	−0.0050 (5)	−0.0024 (5)
C8	0.0263 (7)	0.0181 (6)	0.0176 (6)	0.0027 (5)	−0.0069 (5)	−0.0057 (5)
C9	0.0236 (7)	0.0203 (7)	0.0154 (6)	0.0030 (5)	−0.0060 (5)	−0.0019 (5)
C10	0.0176 (6)	0.0149 (6)	0.0162 (6)	0.0021 (5)	−0.0043 (5)	0.0000 (5)
C11	0.0238 (7)	0.0164 (6)	0.0185 (6)	0.0030 (5)	−0.0062 (5)	0.0023 (5)
C12	0.0241 (7)	0.0131 (6)	0.0246 (7)	0.0015 (5)	−0.0050 (5)	0.0018 (5)
C13	0.0204 (6)	0.0118 (6)	0.0234 (7)	−0.0002 (5)	−0.0055 (5)	−0.0016 (5)
C14	0.0166 (6)	0.0119 (6)	0.0177 (6)	−0.0008 (4)	−0.0044 (5)	−0.0012 (5)
C15	0.0141 (5)	0.0111 (5)	0.0161 (6)	0.0004 (4)	−0.0042 (4)	−0.0006 (4)
C16	0.0141 (5)	0.0114 (5)	0.0150 (5)	0.0008 (4)	−0.0041 (4)	−0.0007 (4)
C17	0.0144 (5)	0.0086 (5)	0.0153 (5)	0.0006 (4)	−0.0048 (4)	−0.0013 (4)
C18	0.0142 (5)	0.0091 (5)	0.0155 (5)	0.0009 (4)	−0.0053 (4)	−0.0009 (4)
C19	0.0130 (5)	0.0087 (5)	0.0161 (6)	0.0006 (4)	−0.0038 (4)	−0.0010 (4)
C20	0.0163 (6)	0.0109 (5)	0.0197 (6)	0.0001 (4)	−0.0059 (5)	−0.0027 (5)
C21	0.0176 (6)	0.0155 (6)	0.0215 (6)	−0.0010 (5)	−0.0087 (5)	−0.0029 (5)
C22	0.0174 (6)	0.0153 (6)	0.0246 (7)	0.0021 (5)	−0.0097 (5)	−0.0007 (5)
C23	0.0172 (6)	0.0112 (5)	0.0244 (7)	0.0035 (5)	−0.0074 (5)	−0.0017 (5)
C24	0.0225 (7)	0.0129 (6)	0.0204 (6)	0.0033 (5)	−0.0077 (5)	−0.0063 (5)

Cl1—C4	1.7397 (16)	C11—C12	1.370 (2)
S1—O3	1.4511 (12)	C11—H11	0.96 (2)
S1—O1	1.4564 (11)	C12—C13	1.412 (2)
S1—O2	1.4584 (11)	C12—H12	0.96 (2)
S1—C1	1.7776 (14)	C13—C14	1.3769 (18)
N1—C23	1.3529 (17)	C13—H13	0.96 (2)
N1—C19	1.3673 (16)	C14—C15	1.4217 (18)
N1—C24	1.4823 (17)	C14—H14	0.965 (19)
C1—C6	1.390 (2)	C15—C16	1.4368 (17)
C1—C2	1.394 (2)	C16—C17	1.5094 (18)
C2—C3	1.395 (2)	C17—C18i	1.5585 (17)
C2—H2	0.96 (2)	C17—C18	1.6005 (18)
C3—C4	1.383 (3)	C17—H17	0.974 (19)
C3—H3	0.97 (3)	C18—C19	1.5000 (18)
C4—C5	1.384 (3)	C18—C17i	1.5585 (17)
C5—C6	1.394 (2)	C18—H18	0.95 (2)
C5—H5	0.98 (3)	C19—C20	1.3932 (18)
C6—H6	0.99 (3)	C20—C21	1.3879 (19)
C7—C16	1.3761 (18)	C20—H20	0.97 (2)
C7—C8	1.4189 (19)	C21—C22	1.388 (2)
C7—H7	0.98 (2)	C21—H21	0.95 (2)
C8—C9	1.371 (2)	C22—C23	1.375 (2)
C8—H8	0.96 (2)	C22—H22	0.98 (2)
C9—C10	1.418 (2)	C23—H23	0.94 (2)
C9—H9	1.00 (2)	C24—H24A	0.97 (2)
C10—C11	1.4237 (19)	C24—H24B	0.95 (2)
C10—C15	1.4282 (18)	C24—H24C	0.96 (2)
O3—S1—O1	113.75 (7)	C14—C13—C12	120.46 (13)
O3—S1—O2	113.02 (7)	C14—C13—H13	120.5 (12)
O1—S1—O2	112.70 (7)	C12—C13—H13	119.0 (12)
O3—S1—C1	105.26 (7)	C13—C14—C15	121.07 (13)
O1—S1—C1	105.65 (7)	C13—C14—H14	118.8 (11)
O2—S1—C1	105.50 (7)	C15—C14—H14	120.1 (11)
C23—N1—C19	121.43 (12)	C14—C15—C10	118.30 (12)
C23—N1—C24	116.89 (11)	C14—C15—C16	122.34 (12)
C19—N1—C24	121.68 (11)	C10—C15—C16	119.33 (12)
C6—C1—C2	120.35 (14)	C7—C16—C15	118.98 (12)
C6—C1—S1	120.19 (11)	C7—C16—C17	123.07 (12)
C2—C1—S1	119.44 (11)	C15—C16—C17	117.77 (11)
C1—C2—C3	119.68 (15)	C16—C17—C18i	118.70 (11)
C1—C2—H2	118.5 (13)	C16—C17—C18	117.06 (11)
C3—C2—H2	121.8 (13)	C18i—C17—C18	90.59 (9)
C4—C3—C2	119.18 (16)	C16—C17—H17	110.6 (11)
C4—C3—H3	122.9 (16)	C18i—C17—H17	109.6 (11)
C2—C3—H3	117.9 (16)	C18—C17—H17	108.5 (10)
C3—C4—C5	121.80 (15)	C19—C18—C17i	117.10 (11)
C3—C4—Cl1	119.17 (15)	C19—C18—C17	115.18 (11)
C5—C4—Cl1	119.03 (15)	C17i—C18—C17	89.41 (9)
C4—C5—C6	118.86 (16)	C19—C18—H18	111.7 (12)
C4—C5—H5	120.9 (15)	C17i—C18—H18	112.1 (12)
C6—C5—H5	120.3 (15)	C17—C18—H18	109.4 (12)
C1—C6—C5	120.13 (16)	N1—C19—C20	117.97 (12)
C1—C6—H6	120.6 (15)	N1—C19—C18	120.58 (11)
C5—C6—H6	119.2 (15)	C20—C19—C18	121.12 (11)
C16—C7—C8	121.32 (13)	C21—C20—C19	120.72 (12)
C16—C7—H7	119.8 (13)	C21—C20—H20	121.6 (12)
C8—C7—H7	118.9 (13)	C19—C20—H20	117.6 (12)
C9—C8—C7	120.64 (13)	C20—C21—C22	119.42 (13)
C9—C8—H8	120.8 (12)	C20—C21—H21	120.9 (13)
C7—C8—H8	118.5 (12)	C22—C21—H21	119.6 (13)
C8—C9—C10	120.03 (13)	C23—C22—C21	118.63 (13)
C8—C9—H9	120.9 (14)	C23—C22—H22	120.2 (13)
C10—C9—H9	119.0 (14)	C21—C22—H22	121.0 (13)
C9—C10—C11	121.36 (13)	N1—C23—C22	121.37 (13)
C9—C10—C15	119.59 (12)	N1—C23—H23	114.0 (13)
C11—C10—C15	119.04 (13)	C22—C23—H23	124.6 (13)
C12—C11—C10	121.14 (13)	N1—C24—H24A	109.0 (12)
C12—C11—H11	122.0 (12)	N1—C24—H24B	107.3 (14)
C10—C11—H11	116.8 (12)	H24A—C24—H24B	111.1 (18)
C11—C12—C13	119.94 (13)	N1—C24—H24C	109.9 (13)
C11—C12—H12	118.9 (12)	H24A—C24—H24C	108.7 (18)
C13—C12—H12	121.2 (12)	H24B—C24—H24C	110.7 (19)
O3—S1—C1—C6	−93.88 (13)	C11—C10—C15—C16	176.00 (12)
O1—S1—C1—C6	145.45 (13)	C8—C7—C16—C15	−1.0 (2)
O2—S1—C1—C6	25.87 (14)	C8—C7—C16—C17	173.93 (13)
O3—S1—C1—C2	84.49 (13)	C14—C15—C16—C7	−178.65 (13)
O1—S1—C1—C2	−36.18 (14)	C10—C15—C16—C7	3.31 (19)
O2—S1—C1—C2	−155.76 (12)	C14—C15—C16—C17	6.13 (19)
C6—C1—C2—C3	−0.4 (2)	C10—C15—C16—C17	−171.91 (12)
S1—C1—C2—C3	−178.75 (12)	C7—C16—C17—C18i	−2.56 (19)
C1—C2—C3—C4	0.5 (2)	C15—C16—C17—C18i	172.45 (11)
C2—C3—C4—C5	−0.4 (3)	C7—C16—C17—C18	−109.58 (14)
C2—C3—C4—Cl1	178.78 (13)	C15—C16—C17—C18	65.43 (15)
C3—C4—C5—C6	0.2 (3)	C16—C17—C18—C19	3.08 (16)
Cl1—C4—C5—C6	−178.95 (13)	C18i—C17—C18—C19	−119.90 (13)
C2—C1—C6—C5	0.2 (2)	C16—C17—C18—C17i	122.98 (13)
S1—C1—C6—C5	178.57 (13)	C18i—C17—C18—C17i	0.0
C4—C5—C6—C1	−0.1 (3)	C23—N1—C19—C20	−6.00 (19)
C16—C7—C8—C9	−1.5 (2)	C24—N1—C19—C20	174.15 (12)
C7—C8—C9—C10	1.7 (2)	C23—N1—C19—C18	167.49 (12)
C8—C9—C10—C11	−178.48 (14)	C24—N1—C19—C18	−12.36 (19)
C8—C9—C10—C15	0.6 (2)	C17i—C18—C19—N1	139.98 (12)
C9—C10—C11—C12	179.41 (14)	C17—C18—C19—N1	−116.85 (13)
C15—C10—C11—C12	0.3 (2)	C17i—C18—C19—C20	−46.74 (17)
C10—C11—C12—C13	1.3 (2)	C17—C18—C19—C20	56.43 (16)
C11—C12—C13—C14	−1.0 (2)	N1—C19—C20—C21	6.1 (2)
C12—C13—C14—C15	−0.9 (2)	C18—C19—C20—C21	−167.36 (13)
C13—C14—C15—C10	2.5 (2)	C19—C20—C21—C22	−0.8 (2)
C13—C14—C15—C16	−175.60 (13)	C20—C21—C22—C23	−4.6 (2)
C9—C10—C15—C14	178.74 (13)	C19—N1—C23—C22	0.6 (2)
C11—C10—C15—C14	−2.1 (2)	C24—N1—C23—C22	−179.56 (13)
C9—C10—C15—C16	−3.1 (2)	C21—C22—C23—N1	4.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3	0.97 (2)	2.51 (2)	3.3762 (18)	147.9 (18)
C17—H17···O2i	0.974 (17)	2.506 (18)	3.3001 (18)	138.6 (13)
C20—H20···O2	0.97 (2)	2.20 (2)	3.1329 (18)	160.5 (19)
C23—H23···O1ii	0.94 (2)	2.41 (2)	3.1554 (17)	135.8 (18)
C24—H24B···O1ii	0.95 (2)	2.57 (2)	3.2009 (18)	124.3 (16)
C9—H9···Cg4iii	1.00 (2)	2.98 (2)	3.4790 (16)	112.1 (16)

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O3	0.97 (2)	2.51 (2)	3.3762 (18)	147.9 (18)
C17—H17⋯O2i	0.974 (17)	2.506 (18)	3.3001 (18)	138.6 (13)
C20—H20⋯O2	0.97 (2)	2.20 (2)	3.1329 (18)	160.5 (19)
C23—H23⋯O1ii	0.94 (2)	2.41 (2)	3.1554 (17)	135.8 (18)
C24—H24B⋯O1ii	0.95 (2)	2.57 (2)	3.2009 (18)	124.3 (16)
C9—H9⋯Cg4iii	1.00 (2)	2.98 (2)	3.4790 (16)	112.1 (16)

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