Crystal structure and Hirshfeld surface analysis of 2-[(2-oxo-2H-chromen-4-yl)­oxy]acetic acid dimethyl sulfoxide monosolvate

The crystal structure of 2-[(2-oxo-2H-chromen-4-yl)­oxy]acetic acid di­methyl­sulfoxide monosolvate is described and the inter­molecular contacts in the crystal analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.063
• wR factor = 0.208
• Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections (too) Low ..        40% Check
PLAT243_ALERT_4_C High   'Solvent' Ueq as Compared to Neighbors of        O6A Check
PLAT243_ALERT_4_C High   'Solvent' Ueq as Compared to Neighbors of       C12A Check
PLAT243_ALERT_4_C High   'Solvent' Ueq as Compared to Neighbors of       C13A Check
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of        S1B Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00505 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C11 H8 O5
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     45.542 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.799 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.638 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          4 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.11 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  3  )        25% Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          3 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         40 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          5 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   7 ALERT type 3 Indicator that the structure quality may be low
   8 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS2018 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and PLATON (Spek, 2009).

2-[(2-Oxo-2H-chromen-4-yl)oxy]acetic acid dimethyl sulfoxide monosolvate

Crystal data

C11H8O5·C2H6OS	F(000) = 1248
Mr = 298.30	Dx = 1.428 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 23.1461 (12) Å	Cell parameters from 6824 reflections
b = 8.2631 (4) Å	θ = 1.8–28.3°
c = 14.6374 (8) Å	µ = 0.26 mm^−1
β = 97.687 (4)°	T = 293 K
V = 2774.4 (2) Å^3	Block, colourless
Z = 8	0.25 × 0.18 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	2743 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.119
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θmax = 28.3°, θmin = 1.8°
Tmin = 0.742, Tmax = 0.852	h = −30→30
25798 measured reflections	k = −10→10
6824 independent reflections	l = −19→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.063	H-atom parameters constrained
wR(F^2) = 0.208	w = 1/[σ^2(Fo^2) + (0.1053P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.87	(Δ/σ)max < 0.001
6824 reflections	Δρmax = 0.69 e Å^−3
376 parameters	Δρmin = −0.41 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C13A	−0.04399 (18)	0.4312 (5)	0.3443 (3)	0.0728 (13)
H13A	−0.070292	0.463777	0.386381	0.109*
H13B	−0.039226	0.315849	0.346833	0.109*
H13C	−0.059577	0.462937	0.282872	0.109*
C13B	0.4520 (2)	0.3039 (6)	0.5340 (4)	0.0918 (16)
H13D	0.491305	0.265054	0.546953	0.138*
H13E	0.427430	0.243383	0.569514	0.138*
H13F	0.450767	0.416386	0.550058	0.138*
C12B	0.4320 (2)	0.0677 (5)	0.4079 (4)	0.0834 (15)
H12A	0.419331	0.033276	0.345850	0.125*
H12B	0.407847	0.018839	0.448683	0.125*
H12C	0.471795	0.035236	0.425574	0.125*
S1B	0.42683 (4)	0.27960 (14)	0.41469 (9)	0.0666 (4)
C8B	0.27020 (14)	0.7563 (4)	0.6754 (2)	0.0410 (9)
H8B	0.286314	0.852257	0.657309	0.049*
C8A	0.22217 (14)	1.1613 (4)	0.5296 (2)	0.0388 (8)
H8A	0.206427	1.062620	0.544340	0.047*
C1A	0.21016 (13)	1.4456 (4)	0.4892 (2)	0.0343 (8)
C1B	0.28007 (13)	0.4732 (4)	0.7173 (2)	0.0365 (8)
C9A	0.18699 (13)	1.2921 (4)	0.5157 (2)	0.0356 (8)
C6B	0.22279 (14)	0.4729 (4)	0.7336 (2)	0.0374 (8)
C7B	0.21038 (14)	0.7526 (4)	0.6883 (3)	0.0408 (9)
C6A	0.26854 (14)	1.4507 (4)	0.4786 (2)	0.0374 (8)
C9B	0.30397 (13)	0.6232 (4)	0.6888 (2)	0.0350 (8)
C10B	0.39088 (14)	0.7553 (4)	0.6567 (3)	0.0450 (9)
H10A	0.365842	0.821170	0.613063	0.054*
H10B	0.425039	0.726291	0.628436	0.054*
C7A	0.28261 (15)	1.1714 (4)	0.5224 (3)	0.0425 (9)
C3A	0.20154 (16)	1.7230 (4)	0.4385 (3)	0.0486 (10)
H3A	0.179056	1.815309	0.424815	0.058*
C4A	0.25956 (17)	1.7231 (4)	0.4274 (3)	0.0502 (10)
H4A	0.275975	1.815759	0.405586	0.060*
C5A	0.29396 (15)	1.5876 (4)	0.4480 (3)	0.0451 (9)
H5A	0.333355	1.588921	0.441346	0.054*
C11B	0.40938 (15)	0.8519 (4)	0.7420 (3)	0.0484 (10)
C5B	0.19577 (16)	0.3353 (4)	0.7620 (3)	0.0469 (9)
H5B	0.157087	0.338287	0.772786	0.056*
C3B	0.28513 (17)	0.1906 (4)	0.7585 (3)	0.0496 (10)
H3B	0.306236	0.094800	0.767083	0.060*
C11A	0.08288 (14)	1.0434 (4)	0.4690 (3)	0.0436 (9)
C4B	0.22748 (17)	0.1949 (4)	0.7737 (3)	0.0501 (10)
H4B	0.209965	0.101248	0.792202	0.060*
C2A	0.17680 (15)	1.5856 (4)	0.4699 (2)	0.0423 (9)
H2A	0.137684	1.586033	0.478387	0.051*
C2B	0.31131 (15)	0.3286 (4)	0.7305 (2)	0.0429 (9)
H2B	0.350099	0.325359	0.720247	0.052*
C12A	0.05788 (19)	0.4705 (5)	0.2783 (3)	0.0771 (14)
H12D	0.063612	0.355485	0.278054	0.116*
H12E	0.033342	0.502275	0.223138	0.116*
H12F	0.094887	0.524054	0.281072	0.116*
C10A	0.10247 (14)	1.1508 (4)	0.5512 (3)	0.0421 (9)
H10C	0.068964	1.179268	0.581190	0.050*
H10D	0.129589	1.091455	0.595162	0.050*
O2B	0.17604 (10)	0.8632 (3)	0.6759 (2)	0.0583 (7)
O2A	0.30431 (9)	1.3180 (3)	0.49654 (17)	0.0443 (6)
O3B	0.36054 (9)	0.6118 (3)	0.67566 (17)	0.0447 (6)
O1A	0.31786 (11)	1.0636 (3)	0.5349 (2)	0.0623 (8)
O1B	0.18850 (9)	0.6100 (3)	0.71963 (17)	0.0455 (6)
O3A	0.13002 (9)	1.2960 (2)	0.52488 (17)	0.0422 (6)
O4A	0.06268 (12)	0.9068 (3)	0.49773 (19)	0.0586 (8)
H4A1	0.050295	0.850621	0.453194	0.088*
O4B	0.43802 (13)	0.9821 (3)	0.7219 (2)	0.0710 (9)
H4B1	0.445425	1.038184	0.768236	0.106*
O7B	0.47513 (11)	0.3440 (3)	0.3654 (2)	0.0764 (10)
O6A	0.01623 (13)	0.6980 (4)	0.3745 (3)	0.0979 (13)
O5B	0.39977 (12)	0.8143 (4)	0.8178 (2)	0.0682 (9)
O5A	0.08491 (13)	1.0796 (4)	0.3906 (2)	0.0718 (9)
S1A	0.02436 (6)	0.52545 (19)	0.37557 (13)	0.0507 (6)	0.782 (5)
S1'A	0.0025 (3)	0.5829 (7)	0.3230 (5)	0.057 (2)	0.218 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C13A	0.067 (3)	0.069 (3)	0.085 (4)	−0.020 (2)	0.016 (2)	−0.009 (3)
C13B	0.086 (3)	0.094 (4)	0.090 (4)	−0.016 (3)	−0.010 (3)	−0.007 (3)
C12B	0.088 (3)	0.070 (3)	0.090 (4)	−0.011 (3)	0.001 (3)	0.004 (3)
S1B	0.0449 (6)	0.0689 (7)	0.0854 (10)	0.0084 (5)	0.0070 (6)	0.0063 (6)
C8B	0.0393 (18)	0.0338 (18)	0.051 (3)	−0.0033 (15)	0.0085 (16)	0.0001 (17)
C8A	0.0399 (18)	0.0315 (17)	0.045 (2)	−0.0033 (14)	0.0075 (16)	0.0018 (16)
C1A	0.0360 (17)	0.0355 (18)	0.032 (2)	0.0010 (14)	0.0049 (15)	−0.0044 (15)
C1B	0.0380 (18)	0.0345 (18)	0.036 (2)	−0.0004 (15)	0.0007 (15)	−0.0001 (16)
C9A	0.0353 (17)	0.0366 (19)	0.035 (2)	−0.0010 (14)	0.0033 (15)	−0.0007 (15)
C6B	0.0432 (19)	0.0366 (18)	0.032 (2)	−0.0007 (15)	0.0052 (16)	−0.0041 (16)
C7B	0.0416 (19)	0.039 (2)	0.042 (2)	−0.0008 (16)	0.0051 (16)	−0.0021 (17)
C6A	0.0445 (19)	0.0345 (18)	0.033 (2)	−0.0015 (15)	0.0059 (16)	−0.0057 (16)
C9B	0.0328 (16)	0.0382 (18)	0.033 (2)	0.0004 (14)	0.0028 (15)	−0.0073 (16)
C10B	0.0347 (17)	0.043 (2)	0.059 (3)	−0.0011 (16)	0.0159 (17)	0.0030 (19)
C7A	0.0432 (19)	0.040 (2)	0.044 (2)	0.0032 (16)	0.0033 (17)	−0.0044 (17)
C3A	0.057 (2)	0.041 (2)	0.048 (3)	0.0097 (18)	0.0062 (19)	0.0031 (18)
C4A	0.071 (3)	0.039 (2)	0.041 (3)	−0.0134 (19)	0.011 (2)	0.0038 (18)
C5A	0.047 (2)	0.045 (2)	0.045 (3)	−0.0090 (17)	0.0108 (18)	−0.0043 (18)
C11B	0.0358 (19)	0.042 (2)	0.069 (3)	−0.0054 (16)	0.014 (2)	−0.004 (2)
C5B	0.050 (2)	0.051 (2)	0.040 (3)	−0.0126 (18)	0.0074 (17)	0.0001 (18)
C3B	0.066 (3)	0.038 (2)	0.042 (3)	0.0018 (18)	−0.0043 (19)	0.0061 (18)
C11A	0.0343 (18)	0.044 (2)	0.053 (3)	−0.0022 (16)	0.0095 (18)	0.000 (2)
C4B	0.070 (3)	0.041 (2)	0.038 (3)	−0.0132 (19)	0.0029 (19)	0.0051 (17)
C2A	0.0445 (19)	0.041 (2)	0.041 (2)	0.0018 (16)	0.0038 (17)	0.0004 (17)
C2B	0.0436 (19)	0.042 (2)	0.042 (2)	0.0022 (16)	0.0001 (17)	−0.0009 (17)
C12A	0.070 (3)	0.076 (3)	0.092 (4)	−0.003 (2)	0.034 (3)	−0.030 (3)
C10A	0.0368 (18)	0.0411 (19)	0.050 (3)	−0.0006 (15)	0.0109 (17)	0.0002 (18)
O2B	0.0477 (15)	0.0467 (15)	0.081 (2)	0.0112 (12)	0.0088 (14)	0.0038 (14)
O2A	0.0367 (12)	0.0435 (14)	0.0539 (18)	0.0010 (10)	0.0101 (11)	0.0052 (12)
O3B	0.0342 (13)	0.0378 (13)	0.0629 (19)	−0.0018 (10)	0.0094 (12)	0.0006 (12)
O1A	0.0475 (15)	0.0520 (16)	0.088 (2)	0.0149 (13)	0.0105 (14)	0.0099 (15)
O1B	0.0392 (13)	0.0430 (14)	0.0561 (18)	0.0005 (11)	0.0123 (12)	0.0030 (12)
O3A	0.0340 (12)	0.0348 (13)	0.0583 (18)	0.0003 (10)	0.0085 (11)	0.0034 (11)
O4A	0.0630 (17)	0.0405 (15)	0.072 (2)	−0.0125 (13)	0.0081 (15)	−0.0035 (14)
O4B	0.0748 (19)	0.0550 (17)	0.085 (2)	−0.0232 (15)	0.0173 (18)	−0.0107 (16)
O7B	0.0494 (16)	0.074 (2)	0.110 (3)	0.0176 (14)	0.0238 (16)	0.0302 (18)
O6A	0.074 (2)	0.073 (2)	0.153 (4)	−0.0240 (17)	0.040 (2)	−0.065 (2)
O5B	0.074 (2)	0.074 (2)	0.058 (2)	−0.0207 (15)	0.0138 (16)	−0.0042 (17)
O5A	0.089 (2)	0.079 (2)	0.049 (2)	−0.0262 (17)	0.0148 (17)	−0.0035 (17)
S1A	0.0455 (8)	0.0497 (9)	0.0550 (13)	0.0045 (6)	−0.0008 (7)	−0.0059 (8)
S1'A	0.059 (3)	0.049 (3)	0.061 (5)	0.004 (3)	0.002 (3)	0.007 (3)

Geometric parameters (Å, º)

C13A—S1'A	1.708 (6)	C10B—H10A	0.9700
C13A—S1A	1.768 (4)	C10B—H10B	0.9700
C13A—H13A	0.9600	C7A—O1A	1.205 (4)
C13A—H13B	0.9600	C7A—O2A	1.384 (4)
C13A—H13C	0.9600	C3A—C2A	1.378 (5)
C13B—S1B	1.777 (5)	C3A—C4A	1.374 (5)
C13B—H13D	0.9600	C3A—H3A	0.9300
C13B—H13E	0.9600	C4A—C5A	1.384 (5)
C13B—H13F	0.9600	C4A—H4A	0.9300
C12B—S1B	1.759 (5)	C5A—H5A	0.9300
C12B—H12A	0.9600	C11B—O5B	1.201 (5)
C12B—H12B	0.9600	C11B—O4B	1.317 (4)
C12B—H12C	0.9600	C5B—C4B	1.372 (5)
S1B—O7B	1.506 (3)	C5B—H5B	0.9300
C8B—C9B	1.348 (4)	C3B—C2B	1.379 (5)
C8B—C7B	1.423 (4)	C3B—C4B	1.383 (5)
C8B—H8B	0.9300	C3B—H3B	0.9300
C8A—C9A	1.352 (4)	C11A—O5A	1.193 (4)
C8A—C7A	1.420 (4)	C11A—O4A	1.312 (4)
C8A—H8A	0.9300	C11A—C10A	1.515 (5)
C1A—C6A	1.382 (4)	C4B—H4B	0.9300
C1A—C2A	1.399 (4)	C2A—H2A	0.9300
C1A—C9A	1.449 (4)	C2B—H2B	0.9300
C1B—C6B	1.378 (4)	C12A—S1'A	1.776 (7)
C1B—C2B	1.396 (4)	C12A—S1A	1.769 (4)
C1B—C9B	1.441 (5)	C12A—H12D	0.9600
C9A—O3A	1.344 (4)	C12A—H12E	0.9600
C6B—C5B	1.388 (5)	C12A—H12F	0.9600
C6B—O1B	1.383 (4)	C10A—O3A	1.436 (4)
C7B—O2B	1.209 (4)	C10A—H10C	0.9700
C7B—O1B	1.384 (4)	C10A—H10D	0.9700
C6A—C5A	1.377 (5)	O4A—H4A1	0.8200
C6A—O2A	1.378 (4)	O4B—H4B1	0.8200
C9B—O3B	1.352 (3)	O6A—S1'A	1.229 (6)
C10B—O3B	1.424 (4)	O6A—S1A	1.438 (3)
C10B—C11B	1.496 (5)
S1A—C13A—H13A	109.5	O2A—C7A—C8A	118.0 (3)
S1A—C13A—H13B	109.5	C2A—C3A—C4A	119.8 (3)
H13A—C13A—H13B	109.5	C2A—C3A—H3A	120.1
S1A—C13A—H13C	109.5	C4A—C3A—H3A	120.1
H13A—C13A—H13C	109.5	C3A—C4A—C5A	121.1 (3)
H13B—C13A—H13C	109.5	C3A—C4A—H4A	119.4
S1B—C13B—H13D	109.5	C5A—C4A—H4A	119.4
S1B—C13B—H13E	109.5	C6A—C5A—C4A	118.5 (3)
H13D—C13B—H13E	109.5	C6A—C5A—H5A	120.8
S1B—C13B—H13F	109.5	C4A—C5A—H5A	120.8
H13D—C13B—H13F	109.5	O5B—C11B—O4B	125.3 (4)
H13E—C13B—H13F	109.5	O5B—C11B—C10B	124.4 (3)
S1B—C12B—H12A	109.5	O4B—C11B—C10B	110.3 (4)
S1B—C12B—H12B	109.5	C4B—C5B—C6B	118.4 (3)
H12A—C12B—H12B	109.5	C4B—C5B—H5B	120.8
S1B—C12B—H12C	109.5	C6B—C5B—H5B	120.8
H12A—C12B—H12C	109.5	C2B—C3B—C4B	119.9 (3)
H12B—C12B—H12C	109.5	C2B—C3B—H3B	120.0
O7B—S1B—C12B	105.3 (2)	C4B—C3B—H3B	120.0
O7B—S1B—C13B	105.3 (2)	O5A—C11A—O4A	125.8 (4)
C12B—S1B—C13B	98.7 (2)	O5A—C11A—C10A	124.8 (3)
C9B—C8B—C7B	121.3 (3)	O4A—C11A—C10A	109.3 (4)
C9B—C8B—H8B	119.4	C5B—C4B—C3B	120.9 (3)
C7B—C8B—H8B	119.4	C5B—C4B—H4B	119.6
C9A—C8A—C7A	121.4 (3)	C3B—C4B—H4B	119.6
C9A—C8A—H8A	119.3	C3A—C2A—C1A	120.4 (3)
C7A—C8A—H8A	119.3	C3A—C2A—H2A	119.8
C6A—C1A—C2A	118.3 (3)	C1A—C2A—H2A	119.8
C6A—C1A—C9A	117.4 (3)	C3B—C2B—C1B	120.6 (3)
C2A—C1A—C9A	124.3 (3)	C3B—C2B—H2B	119.7
C6B—C1B—C2B	117.8 (3)	C1B—C2B—H2B	119.7
C6B—C1B—C9B	117.8 (3)	S1A—C12A—H12D	109.5
C2B—C1B—C9B	124.3 (3)	S1A—C12A—H12E	109.5
O3A—C9A—C8A	125.7 (3)	H12D—C12A—H12E	109.5
O3A—C9A—C1A	114.1 (3)	S1A—C12A—H12F	109.5
C8A—C9A—C1A	120.2 (3)	H12D—C12A—H12F	109.5
C1B—C6B—C5B	122.4 (3)	H12E—C12A—H12F	109.5
C1B—C6B—O1B	121.3 (3)	O3A—C10A—C11A	111.9 (3)
C5B—C6B—O1B	116.3 (3)	O3A—C10A—H10C	109.2
O2B—C7B—O1B	115.5 (3)	C11A—C10A—H10C	109.2
O2B—C7B—C8B	126.6 (3)	O3A—C10A—H10D	109.2
O1B—C7B—C8B	117.9 (3)	C11A—C10A—H10D	109.2
C5A—C6A—O2A	116.3 (3)	H10C—C10A—H10D	107.9
C5A—C6A—C1A	121.9 (3)	C6A—O2A—C7A	121.2 (3)
O2A—C6A—C1A	121.7 (3)	C9B—O3B—C10B	118.8 (2)
C8B—C9B—O3B	126.1 (3)	C7B—O1B—C6B	121.2 (3)
C8B—C9B—C1B	120.4 (3)	C9A—O3A—C10A	118.9 (2)
O3B—C9B—C1B	113.4 (3)	C11A—O4A—H4A1	109.5
O3B—C10B—C11B	112.0 (3)	C11B—O4B—H4B1	109.5
O3B—C10B—H10A	109.2	O6A—S1A—C12A	108.5 (2)
C11B—C10B—H10A	109.2	O6A—S1A—C13A	108.8 (2)
O3B—C10B—H10B	109.2	C12A—S1A—C13A	98.8 (2)
C11B—C10B—H10B	109.2	O6A—S1'A—C13A	124.9 (5)
H10A—C10B—H10B	107.9	O6A—S1'A—C12A	119.4 (5)
O1A—C7A—O2A	115.2 (3)	C13A—S1'A—C12A	100.8 (3)
O1A—C7A—C8A	126.8 (3)
C7A—C8A—C9A—O3A	−177.0 (3)	O3B—C10B—C11B—O5B	−0.3 (5)
C7A—C8A—C9A—C1A	2.4 (5)	O3B—C10B—C11B—O4B	179.0 (3)
C6A—C1A—C9A—O3A	179.9 (3)	C1B—C6B—C5B—C4B	−0.2 (5)
C2A—C1A—C9A—O3A	−3.1 (5)	O1B—C6B—C5B—C4B	177.8 (3)
C6A—C1A—C9A—C8A	0.5 (5)	C6B—C5B—C4B—C3B	0.6 (6)
C2A—C1A—C9A—C8A	177.5 (3)	C2B—C3B—C4B—C5B	−0.4 (6)
C2B—C1B—C6B—C5B	−0.2 (5)	C4A—C3A—C2A—C1A	−1.0 (6)
C9B—C1B—C6B—C5B	−179.4 (3)	C6A—C1A—C2A—C3A	1.9 (5)
C2B—C1B—C6B—O1B	−178.2 (3)	C9A—C1A—C2A—C3A	−175.0 (3)
C9B—C1B—C6B—O1B	2.6 (5)	C4B—C3B—C2B—C1B	0.0 (5)
C9B—C8B—C7B—O2B	−178.0 (4)	C6B—C1B—C2B—C3B	0.3 (5)
C9B—C8B—C7B—O1B	3.1 (5)	C9B—C1B—C2B—C3B	179.5 (3)
C2A—C1A—C6A—C5A	−1.4 (5)	O5A—C11A—C10A—O3A	−6.4 (5)
C9A—C1A—C6A—C5A	175.8 (3)	O4A—C11A—C10A—O3A	174.6 (3)
C2A—C1A—C6A—O2A	179.8 (3)	C5A—C6A—O2A—C7A	−176.2 (3)
C9A—C1A—C6A—O2A	−3.1 (5)	C1A—C6A—O2A—C7A	2.8 (5)
C7B—C8B—C9B—O3B	177.7 (3)	O1A—C7A—O2A—C6A	179.0 (3)
C7B—C8B—C9B—C1B	−0.3 (5)	C8A—C7A—O2A—C6A	0.2 (5)
C6B—C1B—C9B—C8B	−2.6 (5)	C8B—C9B—O3B—C10B	8.3 (5)
C2B—C1B—C9B—C8B	178.2 (3)	C1B—C9B—O3B—C10B	−173.6 (3)
C6B—C1B—C9B—O3B	179.2 (3)	C11B—C10B—O3B—C9B	78.5 (4)
C2B—C1B—C9B—O3B	0.0 (5)	O2B—C7B—O1B—C6B	177.8 (3)
C9A—C8A—C7A—O1A	178.7 (4)	C8B—C7B—O1B—C6B	−3.1 (5)
C9A—C8A—C7A—O2A	−2.7 (5)	C1B—C6B—O1B—C7B	0.3 (5)
C2A—C3A—C4A—C5A	−0.6 (6)	C5B—C6B—O1B—C7B	−177.8 (3)
O2A—C6A—C5A—C4A	178.8 (3)	C8A—C9A—O3A—C10A	−0.4 (5)
C1A—C6A—C5A—C4A	−0.1 (5)	C1A—C9A—O3A—C10A	−179.8 (3)
C3A—C4A—C5A—C6A	1.1 (6)	C11A—C10A—O3A—C9A	−84.3 (3)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C1A–C6A ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4A—H4A1···O6A	0.82	1.82	2.621 (5)	167
O4B—H4B1···S1B^i	0.82	2.70	3.479 (3)	159
O4B—H4B1···O7B^i	0.82	1.78	2.595 (4)	169
C10B—H10A···O1A	0.97	2.49	3.423 (4)	161
C10B—H10B···O7B^ii	0.97	2.37	3.266 (4)	153
C10A—H10C···O6A^iii	0.97	2.38	3.330 (5)	165
C10A—H10D···O2B	0.97	2.40	3.324 (4)	159
C4B—H4B···Cg1^i	0.93	2.88	3.552 (3)	130

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