(8aR,SS)-Di­methyl 3,5,6,7,8,8a-hexa­hydro-4-{[(1S)-exo-2-hydroxy-7,7-di­methyl­bi­cyclo­[2.2.1]­heptan-1-yl]­methyl­sulfinyl}-1,2-naphthalene­di­carboxyl­ate

The title compound, C₂₄H₃₄O₆S, (I), is an enantiopure sulfinyl adduct, prepared via stereocontrolled Diels-Alder cyclo­addition. The solid-state structure of (I) has been determined at room temperature by single-crystal X-ray diffraction. It is chemically similar to other cited structures; however, it presents a peculiar packing arrangement. Ab initio, density-functional theory (DFT) and semi-empirical (AM1, PM3 and PM5) full-geometry optimizations were carried out for (I). Calculated values of the structural parameters have been compared with those obtained by X-ray crystallography.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.042
• wR factor = 0.101
• Data-to-parameter ratio = 9.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.44 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.05 Ratio
PLAT241_ALERT_2_B Check High   U(eq) as Compared to Neighbors ....        C3'
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors ....        C7'
PLAT413_ALERT_2_B Short Inter XH3 .. XHn     H4'A   ..  H10E    ..       2.09 Ang.

Alert level C
PLAT213_ALERT_2_C Atom C4'     has ADP max/min Ratio .............       3.10 prolat
PLAT213_ALERT_2_C Atom C8'     has ADP max/min Ratio .............       3.10 prolat
PLAT213_ALERT_2_C Atom C9'     has ADP max/min Ratio .............       3.10 prolat
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C1'
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C2'
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C9
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C11
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.08
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H4'A   ..  H10A    ..       2.14 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         21

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               2642
           Count of symmetry unique reflns         2076
           Completeness (_total/calc)            127.26%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       566
           Fraction of Friedel pairs measured     0.273
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   5 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  13 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: XSCANS (Siemens, 1989); cell refinement: XSCANS; data reduction: XPREPW (Bruker, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XPW (Bruker, 1997) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PARST97 (Nardelli, 1995) and WinGX (PC Version 1.6.4.05; Farrugia, 1999).

(8aR,SS)-Dimethyl 3,5,6,7,8,8a-hexahydro-4-{[(1S)-exo-2-hydroxy-7,7- dimethylbicyclo[2.2.1]heptan-1-yl]methylsulfinyl}-1,2-naphthalenedicarboxylate

Crystal data

C24H34O6S	Z = 1
Mr = 450.57	F(000) = 242
Triclinic, P1	Dx = 1.266 Mg m^−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8037 (6) Å	Cell parameters from 62 reflections
b = 7.7391 (8) Å	θ = 5.1–20.0°
c = 11.9131 (9) Å	µ = 0.17 mm^−1
α = 84.539 (8)°	T = 298 K
β = 74.277 (6)°	Prismatic, colourless
γ = 78.323 (7)°	0.46 × 0.32 × 0.28 mm
V = 590.77 (9) Å^3

Data collection

Bruker P4 diffractometer	θmax = 25°, θmin = 2.7°
2θ/ω scans	h = −8→1
2643 measured reflections	k = −9→9
2642 independent reflections	l = −14→13
2244 reflections with I > 2σ(I)	3 standard reflections every 197 reflections
Rint = 0.008	intensity decay: 1%

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + (0.0439P)^2 + 0.1716P] where P = (Fo^2 + 2Fc^2)/3
Least-squares matrix: full	(Δ/σ)max < 0.001
R[F^2 > 2σ(F^2)] = 0.042	Δρmax = 0.19 e Å^−3
wR(F^2) = 0.101	Δρmin = −0.23 e Å^−3
S = 1.02	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
2642 reflections	Extinction coefficient: 0.019 (4)
281 parameters	Absolute structure: Flack (1983)
3 restraints	Absolute structure parameter: 0.05 (10)
H-atom parameters constrained

Special details

Experimental. Selected ¹H NMR absorptions: δ 4.04 (dd, J2',3' = 6.5 and 4.6 Hz, H-2'), 3.81 and 3.79 (two s, 2 × OMe), 2.91 and 2.83 (AB system, J10'A,10'B = 13.2 Hz, H2–10'), 1.10 (s, H3–8'), 0.86 (s, H3–9'). Dimethyl (8aS,SS)-3,5,6,7,8,8a-hexahydro-4-[(1S)-isoborneol-10-sulfinyl]- 1,2-naphthalenedicarboxylate was eluted as a solid (m.p. 458–460 K, 48% yield). Selected ¹H NMR absorptions: δ 4.12 (t, J2',3' = 5.6 Hz, H-2'), 3.80 and 3.78 (two s, 2 × OMe), 2.90 and 2.87 (AB system, J10'A,10'B = 13.2 Hz, H2–10'), 1.12 (s, H3–8'), 0.87 (s, H3–9'). Compound (I) was recrystallized from Et₂O–petrol (2:1 v/v) (m.p. 473–475 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S	0.52964 (14)	0.40561 (11)	0.67238 (8)	0.0474 (3)
O1	0.3130 (5)	0.4133 (4)	0.7488 (2)	0.0622 (8)
O2	0.9770 (7)	0.3049 (7)	0.7244 (3)	0.1277 (19)
H2A	1.073	0.3332	0.7433	0.153*
O3	0.5776 (7)	0.4510 (6)	0.0915 (3)	0.0980 (13)
O4	0.2448 (7)	0.5583 (5)	0.1644 (3)	0.0976 (14)
O5	0.0694 (7)	0.1863 (5)	0.4181 (3)	0.0973 (14)
O6	0.2530 (6)	0.2032 (5)	0.2363 (2)	0.0811 (11)
C1	0.4463 (7)	0.4564 (5)	0.2972 (3)	0.0459 (10)
C2	0.3433 (6)	0.3484 (5)	0.3751 (3)	0.0440 (9)
C3	0.3552 (8)	0.3275 (6)	0.4995 (3)	0.0538 (11)
H3A	0.3922	0.2028	0.5194	0.065*
H3B	0.219	0.3712	0.5496	0.065*
C4	0.5098 (6)	0.4231 (5)	0.5236 (3)	0.0444 (10)
C4A	0.6207 (6)	0.5240 (5)	0.4458 (3)	0.0458 (10)
C5	0.7766 (7)	0.6214 (5)	0.4672 (4)	0.0560 (11)
H5A	0.9122	0.5794	0.416	0.067*
H5B	0.7861	0.5978	0.5472	0.067*
C6	0.7138 (9)	0.8202 (5)	0.4451 (4)	0.0678 (13)
H6A	0.5865	0.8648	0.5026	0.081*
H6B	0.8215	0.8795	0.4534	0.081*
C7	0.6812 (9)	0.8604 (6)	0.3229 (4)	0.0715 (14)
H7A	0.6328	0.9862	0.3124	0.086*
H7B	0.8124	0.8278	0.2654	0.086*
C8	0.5235 (9)	0.7597 (5)	0.3040 (4)	0.0630 (12)
H8A	0.5089	0.7844	0.225	0.076*
H8B	0.3894	0.7994	0.3574	0.076*
C8A	0.5916 (7)	0.5582 (5)	0.3240 (3)	0.0483 (10)
H8AA	0.7278	0.5229	0.2695	0.058*
C9	0.4335 (9)	0.4838 (6)	0.1728 (4)	0.0621 (12)
C10	0.2133 (14)	0.5824 (10)	0.0476 (5)	0.145 (3)
H10A	0.0716	0.6366	0.0518	0.174*	0.5
H10B	0.2435	0.4697	0.0131	0.174*	0.5
H10C	0.3041	0.6569	0.0006	0.174*	0.5
H10D	0.3412	0.5389	−0.0081	0.174*	0.5
H10E	0.1693	0.7057	0.0306	0.174*	0.5
H10F	0.1087	0.5186	0.0431	0.174*	0.5
C11	0.2037 (7)	0.2408 (5)	0.3482 (3)	0.0523 (11)
C12	0.1129 (10)	0.1126 (8)	0.2022 (5)	0.0949 (19)
H12A	0.1621	0.0913	0.1204	0.142*
H12B	−0.0235	0.1843	0.2179	0.142*
H12C	0.1074	0.002	0.2459	0.142*
C1'	0.7175 (7)	0.1201 (5)	0.7886 (3)	0.0504 (10)
C2'	0.8408 (8)	0.2386 (8)	0.8247 (4)	0.0771 (15)
H2'A	0.7436	0.3384	0.8655	0.092*
C3'	0.9446 (10)	0.1242 (14)	0.9109 (5)	0.135 (3)
H3'A	0.9016	0.1757	0.9869	0.162*
H3'B	1.0948	0.1067	0.8832	0.162*
C4'	0.8661 (14)	−0.0492 (11)	0.9156 (5)	0.121 (3)
H4'A	0.9509	−0.1512	0.9459	0.146*
C5'	0.6389 (11)	−0.0140 (8)	0.9851 (4)	0.097 (2)
H5'A	0.6207	0.0459	1.0561	0.116*
H5'B	0.584	−0.1225	1.0046	0.116*
C6'	0.5353 (8)	0.1068 (7)	0.8971 (4)	0.0671 (13)
H6'A	0.4303	0.0545	0.8788	0.081*
H6'B	0.4718	0.2223	0.9281	0.081*
C7'	0.8522 (12)	−0.0692 (8)	0.7904 (4)	0.105 (2)
C8'	1.0677 (15)	−0.0880 (13)	0.6994 (6)	0.193 (6)
H8'1	1.1375	0.0037	0.7087	0.232*	0.5
H8'2	1.0483	−0.0781	0.622	0.232*	0.5
H8'3	1.1501	−0.2011	0.7113	0.232*	0.5
H8'4	1.0864	−0.1874	0.6526	0.232*	0.5
H8'5	1.1756	−0.1055	0.7394	0.232*	0.5
H8'6	1.0738	0.0174	0.65	0.232*	0.5
C9'	0.738 (2)	−0.2134 (8)	0.7772 (7)	0.196 (6)
H9'1	0.7377	−0.2164	0.697	0.235*	0.5
H9'2	0.5981	−0.1892	0.8246	0.235*	0.5
H9'3	0.8078	−0.3255	0.8017	0.235*	0.5
H9'4	0.6914	−0.271	0.8519	0.235*	0.5
H9'5	0.831	−0.2982	0.7243	0.235*	0.5
H9'6	0.6213	−0.1619	0.7472	0.235*	0.5
C10'	0.6603 (7)	0.1771 (5)	0.6741 (3)	0.0489 (10)
H10G	0.5703	0.1022	0.6617	0.059*
H10H	0.7854	0.1615	0.6104	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0594 (7)	0.0463 (5)	0.0439 (5)	−0.0154 (5)	−0.0243 (5)	0.0063 (4)
O1	0.055 (2)	0.079 (2)	0.0512 (15)	−0.0098 (17)	−0.0148 (15)	0.0009 (13)
O2	0.104 (3)	0.257 (6)	0.0535 (19)	−0.115 (4)	−0.020 (2)	0.017 (3)
O3	0.104 (3)	0.149 (4)	0.0428 (18)	−0.044 (3)	−0.002 (2)	−0.0163 (19)
O4	0.119 (4)	0.109 (3)	0.060 (2)	0.023 (3)	−0.052 (2)	0.0072 (18)
O5	0.112 (3)	0.140 (3)	0.0547 (19)	−0.084 (3)	0.000 (2)	−0.0114 (19)
O6	0.095 (3)	0.125 (3)	0.0466 (17)	−0.062 (2)	−0.0293 (18)	0.0048 (17)
C1	0.051 (3)	0.046 (2)	0.0394 (19)	−0.004 (2)	−0.0140 (19)	0.0032 (16)
C2	0.049 (2)	0.045 (2)	0.0384 (19)	−0.0080 (19)	−0.0130 (18)	0.0020 (16)
C3	0.069 (3)	0.059 (2)	0.045 (2)	−0.029 (2)	−0.027 (2)	0.0125 (18)
C4	0.056 (3)	0.042 (2)	0.0402 (19)	−0.010 (2)	−0.022 (2)	0.0081 (16)
C4A	0.048 (3)	0.0403 (19)	0.051 (2)	−0.0094 (19)	−0.019 (2)	0.0086 (17)
C5	0.059 (3)	0.053 (2)	0.064 (3)	−0.021 (2)	−0.026 (2)	0.0117 (19)
C6	0.086 (4)	0.054 (2)	0.071 (3)	−0.032 (3)	−0.022 (3)	0.007 (2)
C7	0.097 (4)	0.051 (2)	0.072 (3)	−0.031 (3)	−0.025 (3)	0.017 (2)
C8	0.083 (3)	0.049 (2)	0.060 (3)	−0.016 (2)	−0.028 (3)	0.0189 (19)
C8A	0.052 (3)	0.044 (2)	0.045 (2)	−0.0089 (19)	−0.010 (2)	0.0091 (16)
C9	0.084 (4)	0.057 (2)	0.044 (2)	−0.019 (3)	−0.014 (3)	0.0074 (19)
C10	0.206 (10)	0.152 (6)	0.090 (5)	0.013 (6)	−0.104 (6)	0.022 (4)
C11	0.060 (3)	0.060 (2)	0.043 (2)	−0.017 (2)	−0.021 (2)	0.0068 (18)
C12	0.107 (5)	0.134 (5)	0.074 (3)	−0.061 (4)	−0.048 (3)	0.000 (3)
C1'	0.054 (3)	0.059 (2)	0.040 (2)	−0.009 (2)	−0.019 (2)	0.0092 (17)
C2'	0.065 (3)	0.141 (5)	0.038 (2)	−0.047 (3)	−0.019 (2)	0.008 (2)
C3'	0.064 (4)	0.284 (11)	0.062 (4)	−0.032 (6)	−0.037 (3)	0.023 (5)
C4'	0.121 (6)	0.154 (6)	0.063 (3)	0.047 (5)	−0.044 (4)	0.027 (4)
C5'	0.140 (6)	0.104 (4)	0.055 (3)	−0.038 (5)	−0.040 (4)	0.033 (3)
C6'	0.063 (3)	0.090 (3)	0.052 (2)	−0.029 (3)	−0.018 (2)	0.019 (2)
C7'	0.144 (6)	0.085 (4)	0.063 (3)	0.038 (4)	−0.038 (4)	0.008 (3)
C8'	0.177 (10)	0.225 (9)	0.086 (5)	0.140 (8)	−0.015 (5)	0.010 (5)
C9'	0.415 (19)	0.050 (3)	0.125 (6)	−0.001 (6)	−0.111 (8)	0.012 (3)
C10'	0.063 (3)	0.044 (2)	0.043 (2)	−0.009 (2)	−0.022 (2)	0.0014 (16)

Geometric parameters (Å, º)

S—O1	1.501 (3)	C10—H10E	0.96
S—C4	1.804 (3)	C10—H10F	0.96
S—C10'	1.812 (4)	C12—H12A	0.96
O2—C2'	1.423 (5)	C12—H12B	0.96
O2—H2A	0.82	C12—H12C	0.96
O3—C9	1.182 (6)	C1'—C2'	1.520 (6)
O4—C9	1.323 (6)	C1'—C10'	1.520 (5)
O4—C10	1.453 (6)	C1'—C6'	1.542 (6)
O5—C11	1.176 (5)	C1'—C7'	1.564 (6)
O6—C11	1.329 (5)	C2'—C3'	1.519 (8)
O6—C12	1.449 (6)	C2'—H2'A	0.98
C1—C2	1.337 (5)	C3'—C4'	1.533 (12)
C1—C8A	1.495 (6)	C3'—H3'A	0.97
C1—C9	1.500 (5)	C3'—H3'B	0.97
C2—C11	1.495 (6)	C4'—C5'	1.526 (10)
C2—C3	1.498 (5)	C4'—C7'	1.544 (8)
C3—C4	1.502 (6)	C4'—H4'A	0.98
C3—H3A	0.97	C5'—C6'	1.554 (7)
C3—H3B	0.97	C5'—H5'A	0.97
C4—C4A	1.326 (5)	C5'—H5'B	0.97
C4A—C5	1.505 (6)	C6'—H6'A	0.97
C4A—C8A	1.509 (5)	C6'—H6'B	0.97
C5—C6	1.528 (6)	C7'—C9'	1.523 (11)
C5—H5A	0.97	C7'—C8'	1.558 (10)
C5—H5B	0.97	C8'—H8'1	0.96
C6—C7	1.525 (6)	C8'—H8'2	0.96
C6—H6A	0.97	C8'—H8'3	0.96
C6—H6B	0.97	C8'—H8'4	0.96
C7—C8	1.521 (7)	C8'—H8'5	0.96
C7—H7A	0.97	C8'—H8'6	0.96
C7—H7B	0.97	C9'—H9'1	0.96
C8—C8A	1.549 (5)	C9'—H9'2	0.96
C8—H8A	0.97	C9'—H9'3	0.96
C8—H8B	0.97	C9'—H9'4	0.96
C8A—H8AA	0.98	C9'—H9'5	0.96
C10—H10A	0.96	C9'—H9'6	0.96
C10—H10B	0.96	C10'—H10G	0.97
C10—H10C	0.96	C10'—H10H	0.97
C10—H10D	0.96
O1—S—C4	106.58 (18)	C10'—C1'—C6'	116.3 (4)
O1—S—C10'	107.13 (18)	C2'—C1'—C7'	104.4 (5)
C4—S—C10'	97.93 (16)	C10'—C1'—C7'	114.5 (3)
C2'—O2—H2A	109.5	C6'—C1'—C7'	101.4 (4)
C9—O4—C10	116.6 (5)	O2—C2'—C3'	115.8 (5)
C11—O6—C12	115.9 (4)	O2—C2'—C1'	110.2 (4)
C2—C1—C8A	123.4 (3)	C3'—C2'—C1'	104.4 (5)
C2—C1—C9	123.7 (4)	O2—C2'—H2'A	108.8
C8A—C1—C9	112.9 (3)	C3'—C2'—H2'A	108.8
C1—C2—C11	124.0 (3)	C1'—C2'—H2'A	108.8
C1—C2—C3	122.4 (4)	C2'—C3'—C4'	102.3 (5)
C11—C2—C3	113.7 (3)	C2'—C3'—H3'A	111.3
C2—C3—C4	113.4 (3)	C4'—C3'—H3'A	111.3
C2—C3—H3A	108.9	C2'—C3'—H3'B	111.3
C4—C3—H3A	108.9	C4'—C3'—H3'B	111.3
C2—C3—H3B	108.9	H3'A—C3'—H3'B	109.2
C4—C3—H3B	108.9	C5'—C4'—C3'	106.1 (6)
H3A—C3—H3B	107.7	C5'—C4'—C7'	103.1 (6)
C4A—C4—C3	124.8 (3)	C3'—C4'—C7'	105.2 (5)
C4A—C4—S	119.3 (3)	C5'—C4'—H4'A	113.8
C3—C4—S	115.8 (3)	C3'—C4'—H4'A	113.8
C4—C4A—C5	126.0 (4)	C7'—C4'—H4'A	113.8
C4—C4A—C8A	121.1 (4)	C4'—C5'—C6'	101.5 (4)
C5—C4A—C8A	112.8 (3)	C4'—C5'—H5'A	111.5
C4A—C5—C6	110.9 (4)	C6'—C5'—H5'A	111.5
C4A—C5—H5A	109.5	C4'—C5'—H5'B	111.5
C6—C5—H5A	109.5	C6'—C5'—H5'B	111.5
C4A—C5—H5B	109.5	H5'A—C5'—H5'B	109.3
C6—C5—H5B	109.5	C1'—C6'—C5'	103.7 (4)
H5A—C5—H5B	108.1	C1'—C6'—H6'A	111
C7—C6—C5	110.7 (3)	C5'—C6'—H6'A	111
C7—C6—H6A	109.5	C1'—C6'—H6'B	111
C5—C6—H6A	109.5	C5'—C6'—H6'B	111
C7—C6—H6B	109.5	H6'A—C6'—H6'B	109
C5—C6—H6B	109.5	C9'—C7'—C4'	115.3 (6)
H6A—C6—H6B	108.1	C9'—C7'—C8'	110.4 (7)
C8—C7—C6	111.0 (4)	C4'—C7'—C8'	112.7 (7)
C8—C7—H7A	109.4	C9'—C7'—C1'	112.7 (6)
C6—C7—H7A	109.4	C4'—C7'—C1'	91.3 (4)
C8—C7—H7B	109.4	C8'—C7'—C1'	113.2 (5)
C6—C7—H7B	109.4	C7'—C8'—H8'1	109.5
H7A—C7—H7B	108	C7'—C8'—H8'2	109.5
C7—C8—C8A	111.1 (4)	H8'1—C8'—H8'2	109.5
C7—C8—H8A	109.4	C7'—C8'—H8'3	109.5
C8A—C8—H8A	109.4	H8'1—C8'—H8'3	109.5
C7—C8—H8B	109.4	H8'2—C8'—H8'3	109.5
C8A—C8—H8B	109.4	C7'—C8'—H8'4	109.5
H8A—C8—H8B	108	H8'1—C8'—H8'4	141.1
C1—C8A—C4A	114.5 (3)	H8'2—C8'—H8'4	56.3
C1—C8A—C8	111.8 (4)	H8'3—C8'—H8'4	56.3
C4A—C8A—C8	108.4 (3)	C7'—C8'—H8'5	109.5
C1—C8A—H8AA	107.3	H8'1—C8'—H8'5	56.3
C4A—C8A—H8AA	107.3	H8'2—C8'—H8'5	141.1
C8—C8A—H8AA	107.3	H8'3—C8'—H8'5	56.3
O3—C9—O4	123.7 (4)	H8'4—C8'—H8'5	109.5
O3—C9—C1	123.9 (5)	C7'—C8'—H8'6	109.5
O4—C9—C1	112.3 (4)	H8'1—C8'—H8'6	56.3
O4—C10—H10A	109.5	H8'2—C8'—H8'6	56.3
O4—C10—H10B	109.5	H8'3—C8'—H8'6	141.1
H10A—C10—H10B	109.5	H8'4—C8'—H8'6	109.5
O4—C10—H10C	109.5	H8'5—C8'—H8'6	109.5
H10A—C10—H10C	109.5	C7'—C9'—H9'1	109.5
H10B—C10—H10C	109.5	C7'—C9'—H9'2	109.5
O4—C10—H10D	109.5	H9'1—C9'—H9'2	109.5
H10A—C10—H10D	141.1	C7'—C9'—H9'3	109.5
H10B—C10—H10D	56.3	H9'1—C9'—H9'3	109.5
H10C—C10—H10D	56.3	H9'2—C9'—H9'3	109.5
O4—C10—H10E	109.5	C7'—C9'—H9'4	109.5
H10A—C10—H10E	56.3	H9'1—C9'—H9'4	141.1
H10B—C10—H10E	141.1	H9'2—C9'—H9'4	56.3
H10C—C10—H10E	56.3	H9'3—C9'—H9'4	56.3
H10D—C10—H10E	109.5	C7'—C9'—H9'5	109.5
O4—C10—H10F	109.5	H9'1—C9'—H9'5	56.3
H10A—C10—H10F	56.3	H9'2—C9'—H9'5	141.1
H10B—C10—H10F	56.3	H9'3—C9'—H9'5	56.3
H10C—C10—H10F	141.1	H9'4—C9'—H9'5	109.5
H10D—C10—H10F	109.5	C7'—C9'—H9'6	109.5
H10E—C10—H10F	109.5	H9'1—C9'—H9'6	56.3
O5—C11—O6	122.1 (4)	H9'2—C9'—H9'6	56.3
O5—C11—C2	124.7 (4)	H9'3—C9'—H9'6	141.1
O6—C11—C2	113.1 (4)	H9'4—C9'—H9'6	109.5
O6—C12—H12A	109.5	H9'5—C9'—H9'6	109.5
O6—C12—H12B	109.5	C1'—C10'—S	112.1 (3)
H12A—C12—H12B	109.5	C1'—C10'—H10G	109.2
O6—C12—H12C	109.5	S—C10'—H10G	109.2
H12A—C12—H12C	109.5	C1'—C10'—H10H	109.2
H12B—C12—H12C	109.5	S—C10'—H10H	109.2
C2'—C1'—C10'	114.6 (3)	H10G—C10'—H10H	107.9
C2'—C1'—C6'	104.0 (3)
C8A—C1—C2—C11	−177.7 (4)	C3—C2—C11—O5	21.7 (7)
C9—C1—C2—C11	0.4 (7)	C1—C2—C11—O6	26.2 (6)
C8A—C1—C2—C3	3.6 (6)	C3—C2—C11—O6	−154.9 (4)
C9—C1—C2—C3	−178.4 (4)	C10'—C1'—C2'—O2	−34.8 (6)
C1—C2—C3—C4	−6.2 (6)	C6'—C1'—C2'—O2	−162.9 (4)
C11—C2—C3—C4	174.9 (3)	C7'—C1'—C2'—O2	91.1 (5)
C2—C3—C4—C4A	3.0 (6)	C10'—C1'—C2'—C3'	−159.8 (4)
C2—C3—C4—S	179.2 (3)	C6'—C1'—C2'—C3'	72.1 (5)
O1—S—C4—C4A	138.0 (3)	C7'—C1'—C2'—C3'	−33.8 (5)
C10'—S—C4—C4A	−111.4 (3)	O2—C2'—C3'—C4'	−121.9 (6)
O1—S—C4—C3	−38.5 (3)	C1'—C2'—C3'—C4'	−0.5 (6)
C10'—S—C4—C3	72.1 (3)	C2'—C3'—C4'—C5'	−73.5 (5)
C3—C4—C4A—C5	180.0 (4)	C2'—C3'—C4'—C7'	35.4 (7)
S—C4—C4A—C5	3.8 (6)	C3'—C4'—C5'—C6'	71.8 (5)
C3—C4—C4A—C8A	2.9 (6)	C7'—C4'—C5'—C6'	−38.5 (7)
S—C4—C4A—C8A	−173.3 (3)	C2'—C1'—C6'—C5'	−72.7 (5)
C4—C4A—C5—C6	−119.9 (4)	C10'—C1'—C6'—C5'	160.3 (4)
C8A—C4A—C5—C6	57.3 (5)	C7'—C1'—C6'—C5'	35.5 (5)
C4A—C5—C6—C7	−54.7 (5)	C4'—C5'—C6'—C1'	1.3 (6)
C5—C6—C7—C8	55.4 (6)	C5'—C4'—C7'—C9'	−57.7 (8)
C6—C7—C8—C8A	−57.2 (5)	C3'—C4'—C7'—C9'	−168.7 (7)
C2—C1—C8A—C4A	2.4 (5)	C5'—C4'—C7'—C8'	174.3 (6)
C9—C1—C8A—C4A	−175.8 (4)	C3'—C4'—C7'—C8'	63.3 (8)
C2—C1—C8A—C8	−121.3 (4)	C5'—C4'—C7'—C1'	58.3 (6)
C9—C1—C8A—C8	60.5 (5)	C3'—C4'—C7'—C1'	−52.7 (6)
C4—C4A—C8A—C1	−5.6 (5)	C2'—C1'—C7'—C9'	170.0 (5)
C5—C4A—C8A—C1	176.9 (3)	C10'—C1'—C7'—C9'	−63.9 (6)
C4—C4A—C8A—C8	119.9 (4)	C6'—C1'—C7'—C9'	62.1 (5)
C5—C4A—C8A—C8	−57.6 (5)	C2'—C1'—C7'—C4'	51.8 (6)
C7—C8—C8A—C1	−175.8 (4)	C10'—C1'—C7'—C4'	177.9 (5)
C7—C8—C8A—C4A	57.1 (5)	C6'—C1'—C7'—C4'	−56.1 (6)
C10—O4—C9—O3	6.6 (8)	C2'—C1'—C7'—C8'	−63.7 (6)
C10—O4—C9—C1	−177.0 (5)	C10'—C1'—C7'—C8'	62.3 (7)
C2—C1—C9—O3	−119.1 (6)	C6'—C1'—C7'—C8'	−171.6 (6)
C8A—C1—C9—O3	59.1 (6)	C2'—C1'—C10'—S	−53.0 (5)
C2—C1—C9—O4	64.5 (5)	C6'—C1'—C10'—S	68.6 (4)
C8A—C1—C9—O4	−117.3 (4)	C7'—C1'—C10'—S	−173.6 (4)
C12—O6—C11—O5	8.6 (7)	O1—S—C10'—C1'	−74.2 (3)
C12—O6—C11—C2	−174.7 (4)	C4—S—C10'—C1'	175.7 (3)
C1—C2—C11—O5	−157.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···S	0.97	2.59	3.117 (4)	114
O2—H2A···O1^i	0.82	1.88	2.683 (5)	166
C10′—H10H···O5^i	0.97	2.59	3.534 (6)	166
C3—H3B···O2^ii	0.97	2.36	3.191 (6)	143
C10—H10D···O3	0.96	2.21	2.652 (9)	107
C8′—H8′1···O2	0.96	2.37	3.01 (1)	123
C8′—H8′6···O2	0.96	2.37	3.01 (1)	123

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