Crystal structure of 5-(1,3-di­thian-2-yl)-2H-1,3-benzodioxole

Zukerman-Schpector, J.; Caracelli, I.; Stefani, H.A.; Gozhina, O.; Tiekink, E.R.T.

doi:10.1107/S2056989015002455

Crystal structure of 5-(1,3-dithian-2-yl)-2H-1,3-benzodioxole

J. Zukerman-Schpector, I. Caracelli, H. A. Stefani, O. Gozhina and E. R. T. Tiekink

In the title compound, C₁₁H₁₂O₂S₂, two independent but virtually superimposable molecules, A and B, comprise the asymmetric unit. In each molecule, the 1,3-dithiane ring has a chair conformation with the 1,4-disposed C atoms being above and below the plane through the remaining four atoms. The substituted benzene ring occupies an equatorial position in each case and forms dihedral angles of 85.62 (9) (molecule A) and 85.69 (8)° (molecule B) with the least-squares plane through the 1,3-dithiane ring. The difference between the molecules rests in the conformation of the five-membered 1,3-dioxole ring which is an envelope in molecule A (the methylene C atom is the flap) and almost planar in molecule B (r.m.s. deviation = 0.046 Å). In the crystal, molecules of A self-associate into supramolecular zigzag chains (generated by glide symmetry along the c axis) via methylene C—H

π interactions. Molecules of B form similar chains. The chains pack with no specific directional intermolecular interactions between them.

Keywords: crystal structure; 1,3-dithiane; conformation; 1,3-benzodioxole; C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015002455/hb7361sup1.cif Contains datablocks I, New_Global_Publ_Block
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989015002455/hb7361Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015002455/hb7361Isup3.cml Supplementary material

CCDC reference: 1047484

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R factor = 0.035
wR factor = 0.092
Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....         O1 Check
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....         C7 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2 Report

Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         12 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   1 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Related literature top

The title compound has been prepared previously, see: Ballesteros et al. (2005). For the structure of a related compound containing the same molecular skeleton as in the title compound, i.e. (19R,21R,25S)-(–)-2-(2-menthyloxycarbonyl-3,4-methylenedioxyphenyl)1,3-dithiane, see: Ratajczak-Sitarz et al. (1996).

Experimental top

A solution of the corresponding 2H-1,3-benzodioxole-5-carbaldehyde (0.037 mol, 1 equiv.) in chloroform (20 ml) was combined with an equimolar amount of propane-1,3-dithiol (3.7 ml, 0.037 mol) at room temperature. The solution was stirred for 1 h at this temperature, then cooled to -20 °C after which BF₃ etherate (0.46 ml, 0.0037 mol, 0.1 equiv.) was added drop-wise. The reaction solution was allowed to warm to room temperature and stirred overnight. After this time, the solution was washed three times each with water, 10% aqueous KOH, then water followed by drying over MgSO₄. Evaporation of the solvent furnishes a pure product as colourless crystals in 97% yield. To obtain crystals suitable for X-ray analysis, the product was crystallized from CH₃OH. The spectroscopic data matched those reported in the literature (Ballesteros et al., 2005).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SIR2014 (Burla et al., 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMOL (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structures of the two independent molecules in title compound showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level.
	Fig. 2. Superimposition of the two independent molecules. Molecule A is shown in red and B in blue. The molecules have been superimposed such that the benzene rings are overlapped.
	Fig. 3. A view of the zigzag supramolecular chain comprising molecules of A along the c axis (glide symmetry) mediated by C—H···π interactions are shown as purple dashed lines.
	Fig. 4. A view in projection down the c axis of the unit-cell contents. The C—H···π interactions are shown as purple dashed lines.

5-(1,3-Dithian-2-yl)-2H-1,3-benzodioxole top

Crystal data top

C₁₁H₁₂O₂S₂	F(000) = 1008
M_r = 240.33	D_x = 1.405 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.4765 (3) Å	Cell parameters from 9068 reflections
b = 17.5504 (4) Å	θ = 2.9–25.4°
c = 11.6397 (2) Å	µ = 0.45 mm⁻¹
β = 104.275 (1)°	T = 296 K
V = 2272.05 (9) Å³	Prism, colourless
Z = 8	0.59 × 0.40 × 0.26 mm

Data collection top

Bruker APEXII CCD diffractometer	3759 reflections with I > 2σ(I)
ϕ and ω scans	R_int = 0.020
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θ_max = 25.4°, θ_min = 1.8°
T_min = 0.702, T_max = 0.745	h = −13→13
14839 measured reflections	k = −21→19
4164 independent reflections	l = −14→8

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0459P)² + 0.9363P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4164 reflections	Δρ_max = 0.29 e Å⁻³
271 parameters	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₁₁H₁₂O₂S₂	V = 2272.05 (9) Å³
M_r = 240.33	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.4765 (3) Å	µ = 0.45 mm⁻¹
b = 17.5504 (4) Å	T = 296 K
c = 11.6397 (2) Å	0.59 × 0.40 × 0.26 mm
β = 104.275 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4164 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3759 reflections with I > 2σ(I)
T_min = 0.702, T_max = 0.745	R_int = 0.020
14839 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.03	Δρ_max = 0.29 e Å⁻³
4164 reflections	Δρ_min = −0.44 e Å⁻³
271 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.

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

	x	y	z	U_iso*/U_eq
S1	0.36505 (5)	0.56934 (3)	0.82081 (4)	0.05661 (16)
S2	0.50542 (5)	0.71160 (3)	0.79700 (4)	0.05188 (15)
O1	0.23644 (16)	0.62085 (13)	0.26070 (13)	0.0865 (6)
O2	0.40467 (15)	0.55784 (9)	0.36797 (12)	0.0660 (4)
C1	0.36233 (15)	0.66240 (10)	0.75248 (15)	0.0432 (4)
H1	0.3013	0.6935	0.7762	0.052*
C2	0.4034 (2)	0.59674 (13)	0.97523 (16)	0.0553 (5)
H2A	0.3401	0.6291	0.9899	0.066*
H2B	0.4066	0.5513	1.0234	0.066*
C3	0.52212 (18)	0.63848 (12)	1.01417 (16)	0.0524 (5)
H3A	0.5408	0.6455	1.0994	0.063*
H3B	0.5849	0.6071	0.9962	0.063*
C4	0.5228 (2)	0.71522 (12)	0.95595 (17)	0.0567 (5)
H4A	0.5980	0.7406	0.9919	0.068*
H4B	0.4583	0.7459	0.9720	0.068*
C5	0.32654 (15)	0.65344 (11)	0.62010 (15)	0.0428 (4)
C6	0.22667 (18)	0.69163 (15)	0.55466 (19)	0.0640 (6)
H6	0.1835	0.7230	0.5937	0.077*
C7	0.1889 (2)	0.68440 (18)	0.4319 (2)	0.0779 (7)
H7	0.1215	0.7100	0.3882	0.094*
C8	0.25501 (19)	0.63842 (14)	0.37937 (16)	0.0602 (6)
C9	0.35527 (17)	0.60054 (11)	0.44322 (15)	0.0464 (4)
C10	0.39414 (16)	0.60659 (10)	0.56338 (15)	0.0426 (4)
H10	0.4621	0.5809	0.6056	0.051*
C11	0.3389 (3)	0.57881 (16)	0.25229 (18)	0.0757 (7)
H11A	0.3891	0.6094	0.2143	0.091*
H11B	0.3145	0.5335	0.2047	0.091*
S3	0.09983 (5)	0.28175 (2)	0.03890 (4)	0.04927 (14)
S4	0.16401 (4)	0.44631 (2)	0.00810 (4)	0.04651 (14)
O3	0.33099 (13)	0.39219 (10)	0.48171 (12)	0.0623 (4)
O4	0.17354 (14)	0.42693 (9)	0.56131 (12)	0.0626 (4)
C12	0.07298 (15)	0.38075 (9)	0.06991 (15)	0.0393 (4)
H12	−0.0118	0.3922	0.0342	0.047*
C13	0.05738 (19)	0.28499 (10)	−0.12132 (16)	0.0496 (4)
H13A	0.0628	0.2340	−0.1517	0.060*
H13B	−0.0258	0.3011	−0.1470	0.060*
C14	0.13363 (18)	0.33772 (11)	−0.17442 (16)	0.0484 (4)
H14A	0.1138	0.3306	−0.2597	0.058*
H14B	0.2176	0.3245	−0.1438	0.058*
C15	0.11586 (19)	0.42070 (10)	−0.14730 (16)	0.0504 (5)
H15A	0.0312	0.4330	−0.1756	0.060*
H15B	0.1596	0.4518	−0.1914	0.060*
C16	0.09597 (16)	0.39253 (9)	0.20158 (15)	0.0401 (4)
C17	0.00141 (17)	0.41118 (10)	0.25062 (18)	0.0460 (4)
H17	−0.0757	0.4149	0.2014	0.055*
C18	0.01841 (18)	0.42465 (11)	0.37213 (18)	0.0521 (5)
H18	−0.0452	0.4381	0.4044	0.063*
C19	0.13232 (18)	0.41716 (10)	0.44076 (16)	0.0451 (4)
C20	0.22716 (16)	0.39691 (10)	0.39325 (16)	0.0435 (4)
C21	0.21260 (16)	0.38462 (11)	0.27471 (15)	0.0441 (4)
H21	0.2772	0.3716	0.2437	0.053*
C22	0.2965 (2)	0.40546 (14)	0.58912 (18)	0.0616 (5)
H22A	0.3083	0.3596	0.6371	0.074*
H22B	0.3455	0.4457	0.6338	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0779 (4)	0.0577 (3)	0.0369 (3)	−0.0258 (3)	0.0194 (2)	−0.0058 (2)
S2	0.0583 (3)	0.0509 (3)	0.0473 (3)	−0.0141 (2)	0.0146 (2)	−0.0003 (2)
O1	0.0774 (11)	0.1433 (18)	0.0318 (7)	−0.0069 (11)	0.0003 (7)	−0.0008 (9)
O2	0.0837 (11)	0.0812 (11)	0.0364 (7)	0.0008 (8)	0.0209 (7)	−0.0108 (7)
C1	0.0412 (9)	0.0521 (10)	0.0391 (9)	0.0008 (8)	0.0155 (7)	−0.0036 (8)
C2	0.0696 (13)	0.0651 (13)	0.0352 (9)	−0.0103 (10)	0.0208 (9)	−0.0019 (9)
C3	0.0580 (12)	0.0621 (12)	0.0359 (9)	−0.0002 (9)	0.0092 (8)	−0.0045 (8)
C4	0.0662 (13)	0.0545 (12)	0.0459 (11)	−0.0100 (10)	0.0068 (9)	−0.0122 (9)
C5	0.0380 (9)	0.0554 (11)	0.0370 (9)	−0.0024 (8)	0.0130 (7)	0.0002 (8)
C6	0.0459 (11)	0.0932 (17)	0.0539 (12)	0.0180 (11)	0.0142 (9)	0.0020 (11)
C7	0.0512 (12)	0.124 (2)	0.0516 (12)	0.0217 (14)	−0.0001 (10)	0.0118 (13)
C8	0.0507 (11)	0.0919 (16)	0.0343 (10)	−0.0106 (11)	0.0032 (8)	0.0042 (10)
C9	0.0516 (10)	0.0543 (11)	0.0358 (9)	−0.0091 (8)	0.0155 (8)	−0.0023 (8)
C10	0.0439 (9)	0.0509 (10)	0.0335 (8)	0.0003 (8)	0.0104 (7)	0.0015 (7)
C11	0.0981 (19)	0.0934 (18)	0.0356 (11)	−0.0223 (15)	0.0166 (11)	−0.0127 (11)
S3	0.0712 (3)	0.0321 (2)	0.0429 (3)	−0.0009 (2)	0.0108 (2)	0.00570 (17)
S4	0.0588 (3)	0.0368 (2)	0.0442 (3)	−0.01144 (19)	0.0132 (2)	−0.00229 (18)
O3	0.0544 (8)	0.0930 (11)	0.0390 (7)	0.0080 (7)	0.0104 (6)	−0.0048 (7)
O4	0.0798 (10)	0.0687 (9)	0.0452 (8)	0.0103 (8)	0.0265 (7)	−0.0080 (7)
C12	0.0401 (9)	0.0347 (8)	0.0426 (9)	0.0011 (7)	0.0091 (7)	0.0036 (7)
C13	0.0643 (12)	0.0356 (9)	0.0443 (10)	−0.0069 (8)	0.0046 (9)	−0.0028 (7)
C14	0.0598 (11)	0.0477 (10)	0.0362 (9)	−0.0050 (8)	0.0092 (8)	−0.0039 (8)
C15	0.0677 (12)	0.0404 (10)	0.0420 (10)	−0.0090 (9)	0.0111 (9)	0.0061 (8)
C16	0.0447 (9)	0.0330 (8)	0.0448 (9)	0.0036 (7)	0.0155 (8)	0.0024 (7)
C17	0.0434 (9)	0.0388 (9)	0.0578 (11)	0.0092 (7)	0.0161 (8)	0.0032 (8)
C18	0.0550 (11)	0.0453 (10)	0.0654 (13)	0.0117 (8)	0.0325 (10)	−0.0021 (9)
C19	0.0623 (12)	0.0348 (9)	0.0440 (10)	0.0037 (8)	0.0240 (9)	−0.0034 (7)
C20	0.0460 (10)	0.0436 (10)	0.0424 (9)	0.0032 (8)	0.0136 (8)	0.0000 (7)
C21	0.0411 (9)	0.0535 (11)	0.0412 (9)	0.0062 (8)	0.0169 (8)	−0.0004 (8)
C22	0.0757 (15)	0.0689 (14)	0.0411 (10)	−0.0015 (11)	0.0162 (10)	−0.0090 (10)

Geometric parameters (Å, º) top

S1—C2	1.8071 (18)	S3—C13	1.8084 (18)
S1—C1	1.8136 (19)	S3—C12	1.8163 (17)
S2—C4	1.812 (2)	S4—C15	1.8128 (19)
S2—C1	1.8142 (18)	S4—C12	1.8176 (17)
O1—C8	1.380 (2)	O3—C20	1.372 (2)
O1—C11	1.412 (3)	O3—C22	1.420 (2)
O2—C9	1.377 (2)	O4—C19	1.377 (2)
O2—C11	1.420 (3)	O4—C22	1.419 (3)
C1—C5	1.502 (2)	C12—C16	1.504 (2)
C1—H1	0.9800	C12—H12	0.9800
C2—C3	1.515 (3)	C13—C14	1.507 (3)
C2—H2A	0.9700	C13—H13A	0.9700
C2—H2B	0.9700	C13—H13B	0.9700
C3—C4	1.509 (3)	C14—C15	1.515 (3)
C3—H3A	0.9700	C14—H14A	0.9700
C3—H3B	0.9700	C14—H14B	0.9700
C4—H4A	0.9700	C15—H15A	0.9700
C4—H4B	0.9700	C15—H15B	0.9700
C5—C6	1.383 (3)	C16—C17	1.384 (2)
C5—C10	1.402 (2)	C16—C21	1.405 (2)
C6—C7	1.393 (3)	C17—C18	1.399 (3)
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.353 (3)	C18—C19	1.360 (3)
C7—H7	0.9300	C18—H18	0.9300
C8—C9	1.377 (3)	C19—C20	1.383 (2)
C9—C10	1.363 (2)	C20—C21	1.365 (2)
C10—H10	0.9300	C21—H21	0.9300
C11—H11A	0.9700	C22—H22A	0.9700
C11—H11B	0.9700	C22—H22B	0.9700

C2—S1—C1	99.80 (9)	C13—S3—C12	99.16 (8)
C4—S2—C1	99.93 (9)	C15—S4—C12	100.05 (8)
C8—O1—C11	105.10 (17)	C20—O3—C22	105.77 (15)
C9—O2—C11	104.86 (18)	C19—O4—C22	105.78 (14)
C5—C1—S1	109.05 (13)	C16—C12—S3	109.78 (11)
C5—C1—S2	110.02 (12)	C16—C12—S4	110.05 (12)
S1—C1—S2	112.76 (10)	S3—C12—S4	112.62 (9)
C5—C1—H1	108.3	C16—C12—H12	108.1
S1—C1—H1	108.3	S3—C12—H12	108.1
S2—C1—H1	108.3	S4—C12—H12	108.1
C3—C2—S1	114.00 (13)	C14—C13—S3	113.97 (13)
C3—C2—H2A	108.8	C14—C13—H13A	108.8
S1—C2—H2A	108.8	S3—C13—H13A	108.8
C3—C2—H2B	108.8	C14—C13—H13B	108.8
S1—C2—H2B	108.8	S3—C13—H13B	108.8
H2A—C2—H2B	107.6	H13A—C13—H13B	107.7
C4—C3—C2	113.67 (17)	C13—C14—C15	112.54 (16)
C4—C3—H3A	108.8	C13—C14—H14A	109.1
C2—C3—H3A	108.8	C15—C14—H14A	109.1
C4—C3—H3B	108.8	C13—C14—H14B	109.1
C2—C3—H3B	108.8	C15—C14—H14B	109.1
H3A—C3—H3B	107.7	H14A—C14—H14B	107.8
C3—C4—S2	114.57 (13)	C14—C15—S4	115.01 (13)
C3—C4—H4A	108.6	C14—C15—H15A	108.5
S2—C4—H4A	108.6	S4—C15—H15A	108.5
C3—C4—H4B	108.6	C14—C15—H15B	108.5
S2—C4—H4B	108.6	S4—C15—H15B	108.5
H4A—C4—H4B	107.6	H15A—C15—H15B	107.5
C6—C5—C10	120.29 (17)	C17—C16—C21	120.01 (16)
C6—C5—C1	119.61 (17)	C17—C16—C12	119.63 (16)
C10—C5—C1	120.09 (16)	C21—C16—C12	120.36 (15)
C5—C6—C7	121.8 (2)	C16—C17—C18	121.92 (18)
C5—C6—H6	119.1	C16—C17—H17	119.0
C7—C6—H6	119.1	C18—C17—H17	119.0
C8—C7—C6	116.8 (2)	C19—C18—C17	116.85 (16)
C8—C7—H7	121.6	C19—C18—H18	121.6
C6—C7—H7	121.6	C17—C18—H18	121.6
C7—C8—C9	122.08 (18)	C18—C19—O4	128.74 (17)
C7—C8—O1	128.4 (2)	C18—C19—C20	121.81 (17)
C9—C8—O1	109.6 (2)	O4—C19—C20	109.45 (17)
C10—C9—O2	127.83 (18)	C21—C20—O3	128.03 (16)
C10—C9—C8	122.31 (18)	C21—C20—C19	122.16 (17)
O2—C9—C8	109.86 (16)	O3—C20—C19	109.81 (16)
C9—C10—C5	116.72 (17)	C20—C21—C16	117.23 (16)
C9—C10—H10	121.6	C20—C21—H21	121.4
C5—C10—H10	121.6	C16—C21—H21	121.4
O1—C11—O2	109.06 (18)	O4—C22—O3	108.66 (16)
O1—C11—H11A	109.9	O4—C22—H22A	110.0
O2—C11—H11A	109.9	O3—C22—H22A	110.0
O1—C11—H11B	109.9	O4—C22—H22B	110.0
O2—C11—H11B	109.9	O3—C22—H22B	110.0
H11A—C11—H11B	108.3	H22A—C22—H22B	108.3

C2—S1—C1—C5	−177.74 (12)	C13—S3—C12—C16	176.91 (13)
C2—S1—C1—S2	59.74 (11)	C13—S3—C12—S4	−60.10 (11)
C4—S2—C1—C5	179.08 (13)	C15—S4—C12—C16	−178.87 (12)
C4—S2—C1—S1	−58.95 (11)	C15—S4—C12—S3	58.30 (11)
C1—S1—C2—C3	−59.52 (17)	C12—S3—C13—C14	61.79 (16)
S1—C2—C3—C4	65.6 (2)	S3—C13—C14—C15	−67.4 (2)
C2—C3—C4—S2	−64.9 (2)	C13—C14—C15—S4	65.0 (2)
C1—S2—C4—C3	58.13 (18)	C12—S4—C15—C14	−57.47 (16)
S1—C1—C5—C6	122.30 (18)	S3—C12—C16—C17	−113.76 (16)
S2—C1—C5—C6	−113.55 (18)	S4—C12—C16—C17	121.74 (15)
S1—C1—C5—C10	−57.71 (19)	S3—C12—C16—C21	66.16 (19)
S2—C1—C5—C10	66.4 (2)	S4—C12—C16—C21	−58.33 (19)
C10—C5—C6—C7	0.9 (3)	C21—C16—C17—C18	1.7 (3)
C1—C5—C6—C7	−179.2 (2)	C12—C16—C17—C18	−178.35 (16)
C5—C6—C7—C8	−0.3 (4)	C16—C17—C18—C19	−1.2 (3)
C6—C7—C8—C9	−0.3 (4)	C17—C18—C19—O4	−179.94 (18)
C6—C7—C8—O1	179.1 (2)	C17—C18—C19—C20	−0.2 (3)
C11—O1—C8—C7	172.7 (3)	C22—O4—C19—C18	174.8 (2)
C11—O1—C8—C9	−7.8 (3)	C22—O4—C19—C20	−5.0 (2)
C11—O2—C9—C10	−173.3 (2)	C22—O3—C20—C21	−176.4 (2)
C11—O2—C9—C8	7.3 (2)	C22—O3—C20—C19	3.8 (2)
C7—C8—C9—C10	0.3 (3)	C18—C19—C20—C21	1.2 (3)
O1—C8—C9—C10	−179.17 (18)	O4—C19—C20—C21	−179.04 (17)
C7—C8—C9—O2	179.8 (2)	C18—C19—C20—O3	−178.97 (17)
O1—C8—C9—O2	0.3 (2)	O4—C19—C20—O3	0.8 (2)
O2—C9—C10—C5	−179.15 (18)	O3—C20—C21—C16	179.54 (18)
C8—C9—C10—C5	0.2 (3)	C19—C20—C21—C16	−0.7 (3)
C6—C5—C10—C9	−0.8 (3)	C17—C16—C21—C20	−0.7 (3)
C1—C5—C10—C9	179.21 (16)	C12—C16—C21—C20	179.33 (16)
C8—O1—C11—O2	12.4 (3)	C19—O4—C22—O3	7.3 (2)
C9—O2—C11—O1	−12.2 (2)	C20—O3—C22—O4	−6.8 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C5–C11 and C16–C21 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4b···Cg1ⁱ	0.97	2.77	3.731 (2)	170
C13—H13a···Cg2ⁱⁱ	0.97	2.54	3.4841 (19)	165

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y−1/2, z−3/2.