Erythromycin A dimethyl sulfoxide disolvate 1.43-hydrate.

The title compound, C(37)H(67)NO(13)·2C(2)H(6)OS·1.43H(2)O, is a macrolide anti-biotic with better solubility and better dermal penetration abilities than erythromycin A itself. The asymmetric unit of this form contains one erythromycin A mol-ecule, two dimethyl sulfoxide (DMSO) solvent mol-ecules, a fully occupied water mol-ecule and a partially occupied water mol-ecule with an occupancy factor of 0.432 (11). The 14-membered ring of the erythronolide fragment has a conformation which differs considerably from that in erythromycin A dihydrate [Stephenson, Stowell, Toma, Pfeiffer & Byrn (1997 ▶). J. Pharm. Sci.86, 1239-1244]. One of the two DMSO mol-ecules is disordered over two orientations; the orientation depends on the presence or absence of the second, partially occupied, water mol-ecule. In the crystal, erythromycin mol-ecules are connected by O-H⋯O hydrogen bonds involving the hy-droxy groups and the fully occupied water mol-ecule to form layers parallel to (010). These layers are connected along the b-axis direction only by a possible hydrogen-bonding contact involving the partially occupied water mol-ecule.

Related literature

For a description of the title compound, see: Schmidt et al. (2011 ▶). For general background, see: Woodward et al. (1981 ▶). For crystallization experiments, see: Mirza et al. (2003 ▶). For related structures, see: Stephenson et al. (1997 ▶); Henry & Zhang (2007 ▶); Tian et al. (2009 ▶). For refinement details, see: Flack (1983 ▶); Spek (2009 ▶).

Experimental

Crystal data

C37H67NO13·2C2H6SO·1.43H2O

M = 915.93

Monoclinic,

a = 11.1716 (7) Å

b = 19.4025 (12) Å

c = 12.0025 (7) Å

β = 106.245 (1)°

V = 2497.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.17 mm−1

T = 296 K

0.55 × 0.42 × 0.32 mm

Data collection

Siemens SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.870, T max = 0.947

27453 measured reflections

10520 independent reflections

7109 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.142

S = 1.04

10520 reflections

579 parameters

23 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.34 e Å−3

Absolute structure: Flack (1983 ▶), with 4965 Friedel pairs

Flack parameter: 0.02 (9)

Data collection: SMART (Siemens, 1995 ▶); cell refinement: SAINT (Siemens, 1995 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812005223/sj5188sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005223/sj5188Isup2.hkl

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

C37H67NO13·2C2H6SO·1.43H2O	F(000) = 997
Mr = 915.93	Dx = 1.218 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6074 reflections
a = 11.1716 (7) Å	θ = 3–24°
b = 19.4025 (12) Å	µ = 0.17 mm−1
c = 12.0025 (7) Å	T = 296 K
β = 106.245 (1)°	Block, colourless
V = 2497.8 (3) Å3	0.55 × 0.42 × 0.32 mm
Z = 2

Siemens SMART 1K CCD diffractometer	10520 independent reflections
Radiation source: normal-focus sealed tube	7109 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −14→14
Tmin = 0.870, Tmax = 0.947	k = −24→24
27453 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.062P)2 + 0.61P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
10520 reflections	Δρmax = 0.37 e Å−3
579 parameters	Δρmin = −0.34 e Å−3
23 restraints	Absolute structure: Flack (1983), with 4965 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (9)

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	Occ. (<1)
O1	0.9259 (2)	0.73051 (18)	0.7044 (2)	0.0678 (8)
O3	0.89509 (19)	0.71189 (13)	1.06566 (17)	0.0416 (5)
O5	0.66199 (19)	0.54287 (13)	0.93991 (17)	0.0379 (5)
O6	0.9249 (2)	0.56635 (14)	0.8216 (2)	0.0498 (6)
H6A	0.9900	0.5650	0.8743	0.075*
O7W	0.1470 (3)	0.57984 (19)	1.0016 (2)	0.0695 (8)
H7C	0.129 (4)	0.592 (3)	1.063 (2)	0.11 (2)*
H7D	0.207 (3)	0.552 (2)	1.022 (3)	0.094 (18)*
O8W	0.5845 (8)	0.9276 (5)	0.2582 (8)	0.106 (4)	0.432 (11)
O9	0.5978 (4)	0.47211 (19)	0.4648 (3)	0.0971 (11)
O11	0.7227 (3)	0.63909 (15)	0.4476 (2)	0.0601 (7)
H11B	0.6961	0.6645	0.3916	0.090*
O12	0.5552 (3)	0.73381 (19)	0.3910 (2)	0.0767 (9)
H12A	0.4817	0.7454	0.3714	0.115*
O13	0.7336 (2)	0.77075 (14)	0.68886 (18)	0.0441 (5)
O24	0.8552 (2)	0.73134 (15)	1.3084 (2)	0.0556 (6)
O25	0.9804 (2)	0.62995 (16)	1.4629 (2)	0.0600 (7)
H25B	0.9057	0.6380	1.4505	0.090*
O26	1.0377 (2)	0.63220 (14)	1.17612 (19)	0.0493 (6)
O30	0.7064 (2)	0.47251 (14)	1.0976 (2)	0.0511 (6)
O34	0.4210 (2)	0.56850 (14)	0.9577 (2)	0.0517 (6)
H34B	0.4199	0.5717	0.8893	0.078*
N33	0.3193 (3)	0.46849 (16)	1.0750 (2)	0.0466 (7)
C1	0.8498 (3)	0.75202 (17)	0.7486 (3)	0.0389 (7)
C2	0.8725 (3)	0.76395 (17)	0.8779 (3)	0.0389 (7)
H2A	0.8037	0.7917	0.8895	0.047*
C3	0.8777 (3)	0.69572 (17)	0.9450 (2)	0.0335 (7)
H3A	0.9491	0.6686	0.9375	0.040*
C4	0.7580 (3)	0.65215 (17)	0.9018 (3)	0.0363 (7)
H4A	0.7360	0.6524	0.8168	0.044*
C5	0.7790 (3)	0.57594 (17)	0.9404 (3)	0.0345 (7)
H5A	0.8368	0.5736	1.0185	0.041*
C6	0.8284 (3)	0.52994 (18)	0.8564 (3)	0.0441 (8)
C7	0.7203 (3)	0.5174 (2)	0.7452 (3)	0.0469 (8)
H7A	0.6788	0.4750	0.7556	0.056*
H7B	0.6605	0.5545	0.7385	0.056*
C8	0.7540 (4)	0.51235 (19)	0.6293 (3)	0.0533 (9)
H8A	0.8079	0.5515	0.6250	0.064*
C9	0.6353 (4)	0.5193 (2)	0.5315 (3)	0.0599 (11)
C10	0.5615 (3)	0.5868 (2)	0.5174 (3)	0.0555 (10)
H10A	0.5242	0.5897	0.5821	0.067*
C11	0.6505 (3)	0.6485 (2)	0.5281 (3)	0.0479 (9)
H11A	0.7088	0.6463	0.6061	0.058*
C12	0.5943 (3)	0.7213 (2)	0.5137 (3)	0.0515 (9)
C13	0.7001 (3)	0.7736 (2)	0.5620 (3)	0.0478 (8)
H13A	0.7728	0.7604	0.5363	0.057*
C14	0.9918 (4)	0.8051 (2)	0.9199 (3)	0.0569 (10)
H14A	0.9844	0.8471	0.8762	0.085*
H14B	1.0603	0.7785	0.9093	0.085*
H14C	1.0063	0.8158	1.0007	0.085*
C15	0.6484 (3)	0.6862 (2)	0.9362 (4)	0.0573 (10)
H15A	0.6401	0.7332	0.9105	0.086*
H15B	0.6642	0.6847	1.0190	0.086*
H15C	0.5727	0.6617	0.9003	0.086*
C16	0.8815 (4)	0.46350 (19)	0.9167 (4)	0.0577 (10)
H16A	0.9136	0.4359	0.8653	0.087*
H16B	0.8169	0.4385	0.9379	0.087*
H16C	0.9474	0.4740	0.9853	0.087*
C17	0.8250 (5)	0.4457 (3)	0.6187 (5)	0.0940 (17)
H17A	0.8444	0.4454	0.5457	0.141*
H17B	0.7739	0.4065	0.6229	0.141*
H17C	0.9008	0.4436	0.6808	0.141*
C18	0.4532 (4)	0.5846 (3)	0.4040 (4)	0.0864 (15)
H18A	0.4033	0.5444	0.4040	0.130*
H18B	0.4866	0.5831	0.3385	0.130*
H18C	0.4025	0.6251	0.3991	0.130*
C19	0.4898 (4)	0.7309 (3)	0.5700 (4)	0.0748 (12)
H19A	0.4251	0.6979	0.5386	0.112*
H19B	0.4567	0.7767	0.5547	0.112*
H19C	0.5215	0.7242	0.6522	0.112*
C20	0.6678 (4)	0.8489 (2)	0.5289 (3)	0.0692 (12)
H20A	0.6292	0.8517	0.4459	0.083*
H20B	0.6076	0.8649	0.5677	0.083*
C21	0.7804 (5)	0.8958 (2)	0.5608 (4)	0.0855 (15)
H21A	0.7549	0.9423	0.5386	0.128*
H21B	0.8395	0.8811	0.5210	0.128*
H21C	0.8183	0.8939	0.6431	0.128*
C22	1.0168 (3)	0.7020 (2)	1.1400 (3)	0.0445 (8)
H22A	1.0756	0.7131	1.0954	0.053*
C23	1.0425 (4)	0.7513 (2)	1.2420 (3)	0.0535 (9)
H23A	1.0095	0.7962	1.2135	0.064*
H23B	1.1320	0.7561	1.2734	0.064*
C24	0.9880 (3)	0.7304 (2)	1.3406 (3)	0.0502 (9)
C25	1.0223 (3)	0.6553 (2)	1.3694 (3)	0.0476 (9)
H25A	1.1136	0.6529	1.3941	0.057*
C26	0.9787 (3)	0.6105 (2)	1.2625 (3)	0.0473 (8)
H26A	0.8881	0.6145	1.2312	0.057*
C27	1.0414 (5)	0.7765 (3)	1.4463 (3)	0.0729 (12)
H27A	1.0196	0.8236	1.4260	0.109*
H27B	1.1305	0.7719	1.4711	0.109*
H27C	1.0075	0.7629	1.5082	0.109*
C28	0.7942 (5)	0.7927 (2)	1.2621 (4)	0.0775 (13)
H28A	0.8396	0.8315	1.3027	0.116*
H28B	0.7113	0.7928	1.2707	0.116*
H28C	0.7900	0.7958	1.1813	0.116*
C29	1.0136 (5)	0.5356 (2)	1.2872 (4)	0.0731 (12)
H29A	0.9827	0.5092	1.2175	0.110*
H29B	0.9776	0.5187	1.3457	0.110*
H29C	1.1027	0.5314	1.3140	0.110*
C30	0.6344 (3)	0.52944 (18)	1.0432 (3)	0.0379 (7)
H30A	0.6512	0.5700	1.0939	0.046*
C31	0.6781 (3)	0.4524 (2)	1.2038 (3)	0.0551 (10)
H31A	0.6926	0.4917	1.2571	0.066*
C32	0.5423 (3)	0.4309 (2)	1.1766 (3)	0.0571 (10)
H32A	0.5225	0.4206	1.2486	0.069*
H32B	0.5295	0.3893	1.1301	0.069*
C33	0.4542 (3)	0.48677 (19)	1.1117 (3)	0.0414 (8)
H33A	0.4631	0.5260	1.1647	0.050*
C34	0.4951 (3)	0.51140 (18)	1.0086 (3)	0.0379 (7)
H34A	0.4807	0.4741	0.9512	0.046*
C35	0.7669 (4)	0.3950 (3)	1.2574 (4)	0.0831 (14)
H35A	0.8512	0.4112	1.2729	0.125*
H35B	0.7546	0.3567	1.2047	0.125*
H35C	0.7515	0.3806	1.3286	0.125*
C36	0.2757 (4)	0.4494 (2)	1.1756 (4)	0.0681 (12)
H36A	0.1863	0.4466	1.1525	0.102*
H36B	0.3022	0.4837	1.2352	0.102*
H36C	0.3101	0.4055	1.2049	0.102*
C37	0.2853 (4)	0.4155 (2)	0.9868 (3)	0.0574 (10)
H37A	0.3259	0.3731	1.0169	0.086*
H37B	0.3109	0.4293	0.9202	0.086*
H37C	0.1966	0.4090	0.9648	0.086*
S1	0.25601 (10)	0.59971 (10)	0.65505 (9)	0.0772 (4)
O14	0.3849 (3)	0.5796 (2)	0.7224 (3)	0.0901 (11)
C38	0.2103 (6)	0.6649 (3)	0.7334 (6)	0.118 (2)
H38A	0.2281	0.6514	0.8133	0.177*
H38B	0.1224	0.6729	0.7026	0.177*
H38C	0.2550	0.7063	0.7276	0.177*
C39	0.1537 (5)	0.5351 (4)	0.6804 (5)	0.1078 (19)
H39A	0.1596	0.4947	0.6361	0.162*
H39B	0.0696	0.5520	0.6575	0.162*
H39C	0.1767	0.5237	0.7615	0.162*
S2	0.32316 (11)	0.78019 (6)	0.13850 (11)	0.0831 (4)	0.482 (4)
O15	0.3312 (7)	0.7602 (4)	0.2610 (4)	0.0988 (12)	0.482 (4)
C40	0.3945 (18)	0.7122 (7)	0.0884 (13)	0.129 (3)	0.482 (4)
H40D	0.3430	0.6719	0.0804	0.193*	0.482 (4)
H40E	0.4741	0.7031	0.1426	0.193*	0.482 (4)
H40F	0.4060	0.7239	0.0143	0.193*	0.482 (4)
C41	0.4354 (12)	0.8434 (6)	0.1485 (12)	0.126 (3)	0.482 (4)
H41A	0.4095	0.8850	0.1784	0.189*	0.482 (4)
H41B	0.4456	0.8521	0.0729	0.189*	0.482 (4)
H41C	0.5131	0.8282	0.1997	0.189*	0.482 (4)
S2'	0.32316 (11)	0.78019 (6)	0.13850 (11)	0.0831 (4)	0.518 (4)
O15'	0.3821 (7)	0.8140 (3)	0.2530 (4)	0.0988 (12)	0.518 (4)
C40'	0.3841 (18)	0.6976 (5)	0.1450 (13)	0.129 (3)	0.518 (4)
H40A	0.3503	0.6696	0.1947	0.193*	0.518 (4)
H40B	0.4732	0.6995	0.1752	0.193*	0.518 (4)
H40C	0.3626	0.6780	0.0685	0.193*	0.518 (4)
C41'	0.4084 (12)	0.8139 (7)	0.0506 (10)	0.126 (3)	0.518 (4)
H41D	0.3887	0.8619	0.0367	0.189*	0.518 (4)
H41E	0.3878	0.7896	−0.0219	0.189*	0.518 (4)
H41F	0.4958	0.8089	0.0885	0.189*	0.518 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0607 (16)	0.100 (2)	0.0466 (14)	0.0232 (16)	0.0213 (13)	0.0065 (15)
O3	0.0416 (12)	0.0527 (14)	0.0337 (11)	0.0013 (10)	0.0155 (10)	0.0010 (10)
O5	0.0376 (12)	0.0434 (12)	0.0368 (11)	−0.0056 (10)	0.0174 (9)	0.0028 (10)
O6	0.0447 (13)	0.0531 (14)	0.0593 (15)	−0.0022 (12)	0.0272 (11)	−0.0008 (12)
O7W	0.0553 (17)	0.089 (2)	0.0660 (18)	0.0140 (16)	0.0195 (14)	0.0020 (17)
O8W	0.098 (7)	0.107 (7)	0.108 (7)	0.008 (5)	0.018 (5)	0.035 (5)
O9	0.133 (3)	0.071 (2)	0.085 (2)	−0.027 (2)	0.026 (2)	−0.0360 (19)
O11	0.0719 (18)	0.0600 (17)	0.0573 (16)	−0.0040 (13)	0.0328 (14)	0.0000 (13)
O12	0.079 (2)	0.096 (2)	0.0426 (14)	0.0130 (19)	−0.0045 (13)	−0.0086 (15)
O13	0.0442 (13)	0.0525 (14)	0.0348 (11)	0.0021 (11)	0.0095 (10)	−0.0015 (10)
O24	0.0551 (15)	0.0602 (16)	0.0537 (14)	0.0110 (13)	0.0187 (12)	0.0153 (13)
O25	0.0606 (16)	0.0774 (19)	0.0468 (14)	0.0079 (14)	0.0230 (12)	0.0203 (13)
O26	0.0482 (13)	0.0596 (16)	0.0418 (13)	0.0092 (11)	0.0155 (11)	0.0054 (11)
O30	0.0460 (14)	0.0614 (16)	0.0490 (14)	0.0072 (12)	0.0185 (11)	0.0173 (12)
O34	0.0453 (13)	0.0538 (15)	0.0624 (15)	0.0109 (11)	0.0254 (12)	0.0157 (12)
N33	0.0462 (16)	0.0517 (18)	0.0483 (17)	−0.0118 (14)	0.0235 (13)	−0.0027 (14)
C1	0.0444 (19)	0.0345 (18)	0.0403 (17)	−0.0037 (15)	0.0162 (15)	0.0054 (14)
C2	0.0419 (17)	0.0390 (18)	0.0359 (16)	−0.0019 (14)	0.0109 (14)	−0.0022 (14)
C3	0.0350 (16)	0.0338 (16)	0.0323 (15)	0.0028 (13)	0.0106 (13)	0.0019 (13)
C4	0.0318 (16)	0.0384 (19)	0.0396 (17)	0.0003 (13)	0.0115 (13)	0.0022 (14)
C5	0.0293 (15)	0.0380 (17)	0.0377 (16)	−0.0026 (13)	0.0119 (13)	0.0056 (14)
C6	0.0425 (19)	0.0395 (19)	0.056 (2)	−0.0014 (15)	0.0229 (16)	0.0039 (16)
C7	0.053 (2)	0.046 (2)	0.048 (2)	−0.0054 (16)	0.0236 (16)	−0.0068 (16)
C8	0.075 (3)	0.038 (2)	0.058 (2)	−0.0027 (18)	0.036 (2)	−0.0088 (17)
C9	0.083 (3)	0.054 (3)	0.051 (2)	−0.020 (2)	0.032 (2)	−0.015 (2)
C10	0.056 (2)	0.071 (3)	0.0400 (18)	−0.017 (2)	0.0141 (16)	−0.0113 (18)
C11	0.0454 (19)	0.061 (2)	0.0383 (19)	−0.0096 (17)	0.0137 (15)	−0.0058 (17)
C12	0.048 (2)	0.060 (2)	0.0412 (19)	−0.0007 (18)	0.0044 (16)	−0.0028 (17)
C13	0.059 (2)	0.048 (2)	0.0343 (17)	−0.0002 (17)	0.0096 (15)	0.0023 (15)
C14	0.063 (2)	0.053 (2)	0.052 (2)	−0.0158 (19)	0.0111 (18)	0.0087 (18)
C15	0.040 (2)	0.042 (2)	0.096 (3)	0.0038 (16)	0.028 (2)	0.006 (2)
C16	0.062 (2)	0.043 (2)	0.073 (3)	0.0062 (18)	0.027 (2)	0.0029 (19)
C17	0.127 (4)	0.081 (3)	0.093 (4)	0.023 (3)	0.062 (3)	−0.019 (3)
C18	0.082 (3)	0.104 (4)	0.061 (3)	−0.033 (3)	−0.001 (2)	−0.017 (3)
C19	0.049 (2)	0.092 (3)	0.080 (3)	0.004 (2)	0.014 (2)	−0.011 (3)
C20	0.097 (3)	0.055 (2)	0.047 (2)	0.000 (2)	0.006 (2)	0.0005 (19)
C21	0.144 (5)	0.050 (3)	0.072 (3)	−0.011 (3)	0.044 (3)	−0.002 (2)
C22	0.0383 (18)	0.058 (2)	0.0389 (17)	−0.0050 (16)	0.0140 (15)	0.0011 (16)
C23	0.058 (2)	0.063 (2)	0.0410 (19)	−0.0133 (19)	0.0151 (16)	−0.0005 (17)
C24	0.060 (2)	0.055 (2)	0.0375 (18)	−0.0081 (18)	0.0171 (16)	−0.0008 (16)
C25	0.0391 (18)	0.069 (2)	0.0361 (17)	0.0025 (17)	0.0121 (14)	0.0079 (17)
C26	0.0414 (18)	0.056 (2)	0.0440 (19)	0.0052 (17)	0.0105 (15)	0.0089 (17)
C27	0.104 (3)	0.075 (3)	0.045 (2)	−0.019 (3)	0.028 (2)	−0.014 (2)
C28	0.098 (3)	0.067 (3)	0.068 (3)	0.030 (3)	0.025 (3)	0.014 (2)
C29	0.107 (4)	0.049 (2)	0.064 (3)	0.015 (2)	0.025 (2)	0.010 (2)
C30	0.0440 (18)	0.0349 (18)	0.0380 (17)	−0.0009 (14)	0.0166 (14)	0.0002 (14)
C31	0.053 (2)	0.069 (3)	0.045 (2)	−0.0018 (19)	0.0162 (17)	0.0171 (18)
C32	0.063 (2)	0.062 (2)	0.052 (2)	−0.008 (2)	0.0256 (19)	0.0126 (19)
C33	0.0416 (18)	0.048 (2)	0.0362 (17)	−0.0073 (15)	0.0142 (14)	−0.0032 (15)
C34	0.0397 (17)	0.0386 (18)	0.0393 (17)	−0.0004 (15)	0.0174 (14)	0.0006 (15)
C35	0.074 (3)	0.094 (4)	0.078 (3)	0.005 (3)	0.016 (3)	0.041 (3)
C36	0.072 (3)	0.082 (3)	0.065 (3)	−0.024 (2)	0.043 (2)	−0.012 (2)
C37	0.055 (2)	0.055 (2)	0.063 (2)	−0.0121 (18)	0.0181 (19)	−0.0080 (19)
S1	0.0550 (6)	0.1259 (11)	0.0512 (6)	0.0139 (7)	0.0158 (5)	0.0244 (6)
O14	0.0610 (18)	0.141 (3)	0.0719 (19)	0.027 (2)	0.0256 (15)	0.024 (2)
C38	0.112 (5)	0.118 (5)	0.116 (5)	0.045 (4)	0.019 (4)	0.007 (4)
C39	0.086 (4)	0.140 (5)	0.096 (4)	0.000 (4)	0.025 (3)	0.023 (4)
S2	0.0556 (6)	0.1101 (10)	0.0765 (7)	0.0036 (6)	0.0067 (5)	0.0220 (7)
O15	0.104 (4)	0.108 (3)	0.0781 (11)	−0.003 (2)	0.014 (2)	0.0190 (15)
C40	0.160 (7)	0.121 (3)	0.103 (8)	0.032 (5)	0.032 (7)	0.010 (2)
C41	0.136 (7)	0.148 (5)	0.106 (4)	−0.052 (4)	0.054 (4)	−0.014 (3)
S2'	0.0556 (6)	0.1101 (10)	0.0765 (7)	0.0036 (6)	0.0067 (5)	0.0220 (7)
O15'	0.104 (4)	0.108 (3)	0.0781 (11)	−0.003 (2)	0.014 (2)	0.0190 (15)
C40'	0.160 (7)	0.121 (3)	0.103 (8)	0.032 (5)	0.032 (7)	0.010 (2)
C41'	0.136 (7)	0.148 (5)	0.106 (4)	−0.052 (4)	0.054 (4)	−0.014 (3)

O1—C1	1.197 (4)	C19—H19A	0.9600
O3—C22	1.416 (4)	C19—H19B	0.9600
O3—C3	1.440 (4)	C19—H19C	0.9600
O5—C30	1.383 (3)	C20—C21	1.513 (7)
O5—C5	1.454 (3)	C20—H20A	0.9700
O6—C6	1.445 (4)	C20—H20B	0.9700
O6—H6A	0.8200	C21—H21A	0.9600
O7W—H7C	0.845 (10)	C21—H21B	0.9600
O7W—H7D	0.841 (10)	C21—H21C	0.9600
O9—C9	1.210 (5)	C22—C23	1.517 (5)
O11—C11	1.434 (4)	C22—H22A	0.9800
O11—H11B	0.8200	C23—C24	1.529 (5)
O12—C12	1.436 (4)	C23—H23A	0.9700
O12—H12A	0.8200	C23—H23B	0.9700
O13—C1	1.345 (4)	C24—C25	1.523 (5)
O13—C13	1.464 (4)	C24—C27	1.530 (5)
O24—C28	1.407 (5)	C25—C26	1.512 (5)
O24—C24	1.425 (4)	C25—H25A	0.9800
O25—C25	1.419 (4)	C26—C29	1.513 (5)
O25—H25B	0.8200	C26—H26A	0.9800
O26—C22	1.421 (4)	C27—H27A	0.9600
O26—C26	1.438 (4)	C27—H27B	0.9600
O30—C30	1.414 (4)	C27—H27C	0.9600
O30—C31	1.450 (4)	C28—H28A	0.9600
O34—C34	1.415 (4)	C28—H28B	0.9600
O34—H34B	0.8200	C28—H28C	0.9600
N33—C37	1.448 (5)	C29—H29A	0.9600
N33—C36	1.470 (4)	C29—H29B	0.9600
N33—C33	1.490 (4)	C29—H29C	0.9600
C1—C2	1.519 (4)	C30—C34	1.534 (4)
C2—C14	1.514 (5)	C30—H30A	0.9800
C2—C3	1.542 (4)	C31—C35	1.511 (6)
C2—H2A	0.9800	C31—C32	1.518 (5)
C3—C4	1.544 (4)	C31—H31A	0.9800
C3—H3A	0.9800	C32—C33	1.523 (5)
C4—C15	1.546 (5)	C32—H32A	0.9700
C4—C5	1.548 (4)	C32—H32B	0.9700
C4—H4A	0.9800	C33—C34	1.511 (4)
C5—C6	1.558 (4)	C33—H33A	0.9800
C5—H5A	0.9800	C34—H34A	0.9800
C6—C16	1.516 (5)	C35—H35A	0.9600
C6—C7	1.548 (5)	C35—H35B	0.9600
C7—C8	1.542 (5)	C35—H35C	0.9600
C7—H7A	0.9700	C36—H36A	0.9600
C7—H7B	0.9700	C36—H36B	0.9600
C8—C9	1.512 (6)	C36—H36C	0.9600
C8—C17	1.542 (6)	C37—H37A	0.9600
C8—H8A	0.9800	C37—H37B	0.9600
C9—C10	1.532 (6)	C37—H37C	0.9600
C10—C11	1.537 (5)	S1—O14	1.493 (3)
C10—C18	1.549 (5)	S1—C38	1.735 (6)
C10—H10A	0.9800	S1—C39	1.779 (6)
C11—C12	1.536 (6)	C38—H38A	0.9600
C11—H11A	0.9800	C38—H38B	0.9600
C12—C19	1.514 (5)	C38—H38C	0.9600
C12—C13	1.544 (5)	C39—H39A	0.9600
C13—C20	1.530 (6)	C39—H39B	0.9600
C13—H13A	0.9800	C39—H39C	0.9600
C14—H14A	0.9600	S2—O15	1.498 (5)
C14—H14B	0.9600	S2—C41	1.734 (6)
C14—H14C	0.9600	S2—C40	1.734 (6)
C15—H15A	0.9600	C40—H40D	0.9600
C15—H15B	0.9600	C40—H40E	0.9600
C15—H15C	0.9600	C40—H40F	0.9600
C16—H16A	0.9600	C41—H41A	0.9600
C16—H16B	0.9600	C41—H41B	0.9600
C16—H16C	0.9600	C41—H41C	0.9600
C17—H17A	0.9600	C40'—H40A	0.9600
C17—H17B	0.9600	C40'—H40B	0.9600
C17—H17C	0.9600	C40'—H40C	0.9600
C18—H18A	0.9600	C41'—H41D	0.9600
C18—H18B	0.9600	C41'—H41E	0.9600
C18—H18C	0.9600	C41'—H41F	0.9600
C22—O3—C3	116.0 (2)	H21B—C21—H21C	109.5
C30—O5—C5	120.3 (2)	O3—C22—O26	111.6 (3)
C6—O6—H6A	109.5	O3—C22—C23	110.7 (3)
H7C—O7W—H7D	106 (4)	O26—C22—C23	112.1 (3)
C11—O11—H11B	109.5	O3—C22—H22A	107.4
C12—O12—H12A	109.5	O26—C22—H22A	107.4
C1—O13—C13	119.5 (2)	C23—C22—H22A	107.4
C28—O24—C24	118.0 (3)	C22—C23—C24	115.6 (3)
C25—O25—H25B	109.5	C22—C23—H23A	108.4
C22—O26—C26	115.4 (3)	C24—C23—H23A	108.4
C30—O30—C31	112.4 (2)	C22—C23—H23B	108.4
C34—O34—H34B	109.5	C24—C23—H23B	108.4
C37—N33—C36	110.0 (3)	H23A—C23—H23B	107.4
C37—N33—C33	114.9 (3)	O24—C24—C25	104.5 (3)
C36—N33—C33	111.0 (3)	O24—C24—C23	113.3 (3)
O1—C1—O13	123.8 (3)	C25—C24—C23	107.4 (3)
O1—C1—C2	124.8 (3)	O24—C24—C27	110.7 (3)
O13—C1—C2	111.4 (3)	C25—C24—C27	110.9 (3)
C14—C2—C1	107.5 (3)	C23—C24—C27	109.9 (3)
C14—C2—C3	112.2 (3)	O25—C25—C26	111.9 (3)
C1—C2—C3	112.0 (2)	O25—C25—C24	113.2 (3)
C14—C2—H2A	108.4	C26—C25—C24	110.9 (3)
C1—C2—H2A	108.4	O25—C25—H25A	106.8
C3—C2—H2A	108.4	C26—C25—H25A	106.8
O3—C3—C2	108.2 (2)	C24—C25—H25A	106.8
O3—C3—C4	108.5 (2)	O26—C26—C25	109.9 (3)
C2—C3—C4	113.1 (2)	O26—C26—C29	106.1 (3)
O3—C3—H3A	109.0	C25—C26—C29	112.4 (3)
C2—C3—H3A	109.0	O26—C26—H26A	109.5
C4—C3—H3A	109.0	C25—C26—H26A	109.5
C3—C4—C15	110.7 (3)	C29—C26—H26A	109.5
C3—C4—C5	112.2 (2)	C24—C27—H27A	109.5
C15—C4—C5	113.2 (3)	C24—C27—H27B	109.5
C3—C4—H4A	106.8	H27A—C27—H27B	109.5
C15—C4—H4A	106.8	C24—C27—H27C	109.5
C5—C4—H4A	106.8	H27A—C27—H27C	109.5
O5—C5—C4	111.1 (2)	H27B—C27—H27C	109.5
O5—C5—C6	103.0 (2)	O24—C28—H28A	109.5
C4—C5—C6	113.9 (2)	O24—C28—H28B	109.5
O5—C5—H5A	109.5	H28A—C28—H28B	109.5
C4—C5—H5A	109.5	O24—C28—H28C	109.5
C6—C5—H5A	109.5	H28A—C28—H28C	109.5
O6—C6—C16	109.3 (3)	H28B—C28—H28C	109.5
O6—C6—C7	107.0 (3)	C26—C29—H29A	109.5
C16—C6—C7	112.6 (3)	C26—C29—H29B	109.5
O6—C6—C5	109.6 (3)	H29A—C29—H29B	109.5
C16—C6—C5	109.9 (3)	C26—C29—H29C	109.5
C7—C6—C5	108.4 (3)	H29A—C29—H29C	109.5
C8—C7—C6	117.4 (3)	H29B—C29—H29C	109.5
C8—C7—H7A	108.0	O5—C30—O30	108.7 (2)
C6—C7—H7A	108.0	O5—C30—C34	105.3 (2)
C8—C7—H7B	108.0	O30—C30—C34	110.5 (2)
C6—C7—H7B	108.0	O5—C30—H30A	110.7
H7A—C7—H7B	107.2	O30—C30—H30A	110.7
C9—C8—C17	111.7 (3)	C34—C30—H30A	110.7
C9—C8—C7	108.2 (3)	O30—C31—C35	107.1 (3)
C17—C8—C7	112.9 (3)	O30—C31—C32	109.6 (3)
C9—C8—H8A	107.9	C35—C31—C32	112.8 (3)
C17—C8—H8A	107.9	O30—C31—H31A	109.1
C7—C8—H8A	107.9	C35—C31—H31A	109.1
O9—C9—C8	120.9 (4)	C32—C31—H31A	109.1
O9—C9—C10	119.8 (4)	C31—C32—C33	112.3 (3)
C8—C9—C10	119.3 (3)	C31—C32—H32A	109.2
C9—C10—C11	109.9 (3)	C33—C32—H32A	109.2
C9—C10—C18	109.7 (3)	C31—C32—H32B	109.2
C11—C10—C18	115.0 (3)	C33—C32—H32B	109.2
C9—C10—H10A	107.3	H32A—C32—H32B	107.9
C11—C10—H10A	107.3	N33—C33—C34	110.3 (3)
C18—C10—H10A	107.3	N33—C33—C32	115.9 (3)
O11—C11—C12	109.3 (3)	C34—C33—C32	110.1 (3)
O11—C11—C10	108.5 (3)	N33—C33—H33A	106.7
C12—C11—C10	118.2 (3)	C34—C33—H33A	106.7
O11—C11—H11A	106.8	C32—C33—H33A	106.7
C12—C11—H11A	106.8	O34—C34—C33	109.0 (3)
C10—C11—H11A	106.8	O34—C34—C30	111.4 (3)
O12—C12—C19	112.7 (3)	C33—C34—C30	111.5 (3)
O12—C12—C11	105.6 (3)	O34—C34—H34A	108.3
C19—C12—C11	113.9 (3)	C33—C34—H34A	108.3
O12—C12—C13	104.8 (3)	C30—C34—H34A	108.3
C19—C12—C13	110.9 (3)	C31—C35—H35A	109.5
C11—C12—C13	108.5 (3)	C31—C35—H35B	109.5
O13—C13—C20	106.2 (3)	H35A—C35—H35B	109.5
O13—C13—C12	108.1 (3)	C31—C35—H35C	109.5
C20—C13—C12	115.5 (3)	H35A—C35—H35C	109.5
O13—C13—H13A	108.9	H35B—C35—H35C	109.5
C20—C13—H13A	108.9	N33—C36—H36A	109.5
C12—C13—H13A	108.9	N33—C36—H36B	109.5
C2—C14—H14A	109.5	H36A—C36—H36B	109.5
C2—C14—H14B	109.5	N33—C36—H36C	109.5
H14A—C14—H14B	109.5	H36A—C36—H36C	109.5
C2—C14—H14C	109.5	H36B—C36—H36C	109.5
H14A—C14—H14C	109.5	N33—C37—H37A	109.5
H14B—C14—H14C	109.5	N33—C37—H37B	109.5
C4—C15—H15A	109.5	H37A—C37—H37B	109.5
C4—C15—H15B	109.5	N33—C37—H37C	109.5
H15A—C15—H15B	109.5	H37A—C37—H37C	109.5
C4—C15—H15C	109.5	H37B—C37—H37C	109.5
H15A—C15—H15C	109.5	O14—S1—C38	106.4 (3)
H15B—C15—H15C	109.5	O14—S1—C39	107.0 (2)
C6—C16—H16A	109.5	C38—S1—C39	96.9 (3)
C6—C16—H16B	109.5	S1—C38—H38A	109.5
H16A—C16—H16B	109.5	S1—C38—H38B	109.5
C6—C16—H16C	109.5	H38A—C38—H38B	109.5
H16A—C16—H16C	109.5	S1—C38—H38C	109.5
H16B—C16—H16C	109.5	H38A—C38—H38C	109.5
C8—C17—H17A	109.5	H38B—C38—H38C	109.5
C8—C17—H17B	109.5	S1—C39—H39A	109.5
H17A—C17—H17B	109.5	S1—C39—H39B	109.5
C8—C17—H17C	109.5	H39A—C39—H39B	109.5
H17A—C17—H17C	109.5	S1—C39—H39C	109.5
H17B—C17—H17C	109.5	H39A—C39—H39C	109.5
C10—C18—H18A	109.5	H39B—C39—H39C	109.5
C10—C18—H18B	109.5	O15—S2—C41	105.7 (5)
H18A—C18—H18B	109.5	O15—S2—C40	103.7 (6)
C10—C18—H18C	109.5	C41—S2—C40	99.7 (9)
H18A—C18—H18C	109.5	S2—C40—H40D	109.5
H18B—C18—H18C	109.5	S2—C40—H40E	109.5
C12—C19—H19A	109.5	H40D—C40—H40E	109.5
C12—C19—H19B	109.5	S2—C40—H40F	109.5
H19A—C19—H19B	109.5	H40D—C40—H40F	109.5
C12—C19—H19C	109.5	H40E—C40—H40F	109.5
H19A—C19—H19C	109.5	S2—C41—H41A	109.5
H19B—C19—H19C	109.5	S2—C41—H41B	109.5
C21—C20—C13	112.9 (4)	H41A—C41—H41B	109.5
C21—C20—H20A	109.0	S2—C41—H41C	109.5
C13—C20—H20A	109.0	H41A—C41—H41C	109.5
C21—C20—H20B	109.0	H41B—C41—H41C	109.5
C13—C20—H20B	109.0	H40A—C40'—H40B	109.5
H20A—C20—H20B	107.8	H40A—C40'—H40C	109.5
C20—C21—H21A	109.5	H40B—C40'—H40C	109.5
C20—C21—H21B	109.5	H41D—C41'—H41E	109.5
H21A—C21—H21B	109.5	H41D—C41'—H41F	109.5
C20—C21—H21C	109.5	H41E—C41'—H41F	109.5
H21A—C21—H21C	109.5
C13—O13—C1—O1	−7.9 (5)	C19—C12—C13—O13	50.4 (4)
C13—O13—C1—C2	170.3 (3)	C11—C12—C13—O13	−75.4 (3)
O1—C1—C2—C14	49.6 (4)	O12—C12—C13—C20	53.5 (4)
O13—C1—C2—C14	−128.6 (3)	C19—C12—C13—C20	−68.4 (4)
O1—C1—C2—C3	−74.1 (4)	C11—C12—C13—C20	165.8 (3)
O13—C1—C2—C3	107.8 (3)	O13—C13—C20—C21	70.1 (4)
C22—O3—C3—C2	−103.4 (3)	C12—C13—C20—C21	−170.1 (3)
C22—O3—C3—C4	133.6 (3)	C3—O3—C22—O26	−83.3 (3)
C14—C2—C3—O3	61.1 (3)	C3—O3—C22—C23	151.0 (3)
C1—C2—C3—O3	−178.0 (2)	C26—O26—C22—O3	−75.0 (3)
C14—C2—C3—C4	−178.7 (3)	C26—O26—C22—C23	49.9 (4)
C1—C2—C3—C4	−57.8 (3)	O3—C22—C23—C24	79.8 (4)
O3—C3—C4—C15	49.2 (3)	O26—C22—C23—C24	−45.6 (4)
C2—C3—C4—C15	−70.8 (3)	C28—O24—C24—C25	−171.9 (3)
O3—C3—C4—C5	−78.2 (3)	C28—O24—C24—C23	−55.2 (4)
C2—C3—C4—C5	161.7 (2)	C28—O24—C24—C27	68.7 (4)
C30—O5—C5—C4	−105.4 (3)	C22—C23—C24—O24	−66.5 (4)
C30—O5—C5—C6	132.3 (3)	C22—C23—C24—C25	48.4 (4)
C3—C4—C5—O5	157.8 (2)	C22—C23—C24—C27	169.1 (3)
C15—C4—C5—O5	31.6 (4)	O24—C24—C25—O25	−61.2 (3)
C3—C4—C5—C6	−86.4 (3)	C23—C24—C25—O25	178.1 (3)
C15—C4—C5—C6	147.4 (3)	C27—C24—C25—O25	58.0 (4)
O5—C5—C6—O6	163.7 (2)	O24—C24—C25—C26	65.4 (3)
C4—C5—C6—O6	43.3 (3)	C23—C24—C25—C26	−55.2 (4)
O5—C5—C6—C16	−76.2 (3)	C27—C24—C25—C26	−175.3 (3)
C4—C5—C6—C16	163.4 (3)	C22—O26—C26—C25	−58.2 (3)
O5—C5—C6—C7	47.3 (3)	C22—O26—C26—C29	−180.0 (3)
C4—C5—C6—C7	−73.1 (3)	O25—C25—C26—O26	−171.7 (3)
O6—C6—C7—C8	27.4 (4)	C24—C25—C26—O26	60.9 (4)
C16—C6—C7—C8	−92.7 (4)	O25—C25—C26—C29	−53.9 (4)
C5—C6—C7—C8	145.5 (3)	C24—C25—C26—C29	178.8 (3)
C6—C7—C8—C9	−165.1 (3)	C5—O5—C30—O30	−74.8 (3)
C6—C7—C8—C17	70.7 (5)	C5—O5—C30—C34	166.8 (2)
C17—C8—C9—O9	9.0 (5)	C31—O30—C30—O5	−176.7 (3)
C7—C8—C9—O9	−115.9 (4)	C31—O30—C30—C34	−61.7 (3)
C17—C8—C9—C10	−171.5 (3)	C30—O30—C31—C35	−176.0 (3)
C7—C8—C9—C10	63.6 (4)	C30—O30—C31—C32	61.3 (4)
O9—C9—C10—C11	−134.4 (4)	O30—C31—C32—C33	−55.0 (4)
C8—C9—C10—C11	46.0 (4)	C35—C31—C32—C33	−174.2 (3)
O9—C9—C10—C18	−6.9 (5)	C37—N33—C33—C34	58.7 (4)
C8—C9—C10—C18	173.5 (3)	C36—N33—C33—C34	−175.7 (3)
C9—C10—C11—O11	53.6 (4)	C37—N33—C33—C32	−67.3 (4)
C18—C10—C11—O11	−70.9 (4)	C36—N33—C33—C32	58.3 (4)
C9—C10—C11—C12	178.6 (3)	C31—C32—C33—N33	176.4 (3)
C18—C10—C11—C12	54.2 (4)	C31—C32—C33—C34	50.4 (4)
O11—C11—C12—O12	40.4 (4)	N33—C33—C34—O34	57.6 (3)
C10—C11—C12—O12	−84.3 (4)	C32—C33—C34—O34	−173.3 (3)
O11—C11—C12—C19	164.5 (3)	N33—C33—C34—C30	−179.0 (3)
C10—C11—C12—C19	39.9 (4)	C32—C33—C34—C30	−49.9 (4)
O11—C11—C12—C13	−71.4 (3)	O5—C30—C34—O34	−65.0 (3)
C10—C11—C12—C13	163.9 (3)	O30—C30—C34—O34	177.9 (2)
C1—O13—C13—C20	−117.1 (3)	O5—C30—C34—C33	173.0 (3)
C1—O13—C13—C12	118.3 (3)	O30—C30—C34—C33	55.8 (3)
O12—C12—C13—O13	172.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O7Wi	0.82	2.00	2.810 (4)	170
O7W—H7C···O26ii	0.85 (1)	2.07 (2)	2.888 (4)	163 (4)
O7W—H7D···N33	0.84 (1)	2.04 (2)	2.863 (4)	166 (5)
O11—H11B···O12	0.82	2.07	2.575 (4)	120
O12—H12A···O15	0.82	1.85	2.602 (8)	152
O12—H12A···O15′	0.82	2.04	2.667 (7)	134
O25—H25B···O11iii	0.82	2.04	2.838 (4)	166
O34—H34B···O14	0.82	1.94	2.747 (4)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O7Wi	0.82	2.00	2.810 (4)	170
O7W—H7C⋯O26ii	0.85 (1)	2.07 (2)	2.888 (4)	163 (4)
O7W—H7D⋯N33	0.84 (1)	2.04 (2)	2.863 (4)	166 (5)
O11—H11B⋯O12	0.82	2.07	2.575 (4)	120
O12—H12A⋯O15	0.82	1.85	2.602 (8)	152
O12—H12A⋯O15′	0.82	2.04	2.667 (7)	134
O25—H25B⋯O11iii	0.82	2.04	2.838 (4)	166
O34—H34B⋯O14	0.82	1.94	2.747 (4)	170

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