rac-(1R,11R,14S,18R)-Methyl 18-hydroxy-19-oxotri­cyclo­[9.7.1.0^1,14]­nona­decane-11-carboxyl­ate

The investigated crystal of the title compound, C₂₁H₃₄O₄, contains two mol­ecules in the asymmetric unit. One mol­ecule shows disorder for two atoms in the 12-membered ring. The two independent mol­ecules show only slight conformational differences. Four mol­ecules are linked via two O—H...O hydrogen bonds [O...O = 2.816 (2) Å and O—H...O = 163°; O...O = 2.764 (2) Å and O—H...O = 163°] and a centrosymmetric 16-membered heterocycle containing four hydrogen bonds is formed.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.071
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT390_ALERT_3_A Deviating Methyl C5'     X-C-H Bond Angle ......     125.30 Deg.

Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         34 Perc.
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.84 Ratio
PLAT241_ALERT_2_B Check High   U(eq) as Compared to Neighbors ....         C5

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.92 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.40 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C4'
PLAT301_ALERT_3_C Main Residue  Disorder .........................       4.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         28
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C21 H34 O4

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

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

---

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).

(I)

Crystal data

C21H34O4	F(000) = 1536
Mr = 350.48	Dx = 1.169 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 31011 reflections
a = 10.5029 (9) Å	θ = 3.0–25.3°
b = 11.0460 (2) Å	µ = 0.08 mm^−1
c = 34.5904 (9) Å	T = 291 K
β = 97.055 (1)°	Block, colourless
V = 3982.6 (4) Å^3	0.20 × 0.15 × 0.15 mm
Z = 8

Data collection

Nonius KappaCCD diffractometer	2449 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
Graphite monochromator	θmax = 25.3°, θmin = 3.0°
Detector resolution: 19 vertical, 18 horizontal pixels mm^-1	h = −12→12
496 frames via ω–rotation (Δω = 1°) and two times 55 s per frame (four sets at different κ–angles) scans	k = −13→13
31011 measured reflections	l = −41→41
7110 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.071	w = 1/[σ^2(Fo^2) + (0.0101P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.91	(Δ/σ)max = 0.001
7110 reflections	Δρmax = 0.22 e Å^−3
474 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00321 (18)

Special details

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.86853 (16)	1.08978 (13)	0.06918 (5)	0.0659 (5)
H1	0.8262	1.0273	0.0684	0.099*
O2	0.81901 (15)	1.34704 (13)	0.14951 (4)	0.0587 (5)
O3	0.65103 (19)	1.40753 (16)	0.23271 (5)	0.0947 (7)
O4	0.56666 (18)	1.37228 (15)	0.17160 (5)	0.0761 (6)
C1	0.8031 (2)	1.1359 (2)	0.13409 (7)	0.0383 (6)
C2	0.9316 (2)	1.07495 (19)	0.15007 (6)	0.0562 (7)
H2A	0.9270	1.0525	0.1770	0.067*
H2B	0.9394	1.0006	0.1356	0.067*
C3	1.0527 (3)	1.1478 (2)	0.14864 (7)	0.0792 (9)
H3A	1.0430	1.2263	0.1605	0.095*
H3B	1.0656	1.1611	0.1217	0.095*
C4	1.1705 (3)	1.0843 (2)	0.16976 (10)	0.1104 (12)
H4A	1.1416	1.0265	0.1879	0.133*
H4B	1.2113	1.0387	0.1507	0.133*
C5	1.2688 (3)	1.1632 (3)	0.19148 (12)	0.1474 (15)
H5A	1.3151	1.2037	0.1726	0.177*
H5B	1.3296	1.1115	0.2071	0.177*
C6	1.2239 (3)	1.2599 (3)	0.21836 (11)	0.1211 (13)
H6A	1.1718	1.3193	0.2030	0.145*
H6B	1.2979	1.3013	0.2318	0.145*
C7	1.1442 (3)	1.2023 (3)	0.24878 (10)	0.1220 (13)
H7A	1.0914	1.1376	0.2365	0.146*
H7B	1.2020	1.1675	0.2699	0.146*
C8	1.0579 (3)	1.2965 (3)	0.26535 (8)	0.0988 (11)
H8A	1.1069	1.3697	0.2720	0.119*
H8B	1.0292	1.2652	0.2890	0.119*
C9	0.9400 (3)	1.3274 (2)	0.23579 (7)	0.0718 (8)
H9A	0.9013	1.4016	0.2438	0.086*
H9B	0.9680	1.3417	0.2105	0.086*
C10	0.8387 (2)	1.2268 (2)	0.23204 (6)	0.0607 (8)
H10A	0.8005	1.2238	0.2562	0.073*
H10B	0.8824	1.1504	0.2296	0.073*
C11	0.7290 (2)	1.2362 (2)	0.19810 (7)	0.0445 (7)
C12	0.6373 (2)	1.1269 (2)	0.19999 (6)	0.0556 (7)
H12A	0.6352	1.1054	0.2271	0.067*
H12B	0.5514	1.1516	0.1894	0.067*
C13	0.6740 (2)	1.01515 (18)	0.17803 (6)	0.0509 (7)
H13A	0.6072	0.9545	0.1781	0.061*
H13B	0.7528	0.9813	0.1913	0.061*
C14	0.6928 (2)	1.04518 (19)	0.13573 (6)	0.0436 (7)
H14	0.7173	0.9700	0.1236	0.052*
C15	0.5655 (2)	1.08768 (19)	0.11295 (7)	0.0606 (8)
H15A	0.5018	1.0242	0.1132	0.073*
H15B	0.5347	1.1583	0.1256	0.073*
C16	0.5816 (2)	1.1190 (2)	0.07098 (7)	0.0671 (8)
H16A	0.6085	1.0479	0.0577	0.081*
H16B	0.5006	1.1468	0.0574	0.081*
C17	0.6821 (3)	1.2180 (2)	0.07121 (7)	0.0651 (8)
H17A	0.6919	1.2399	0.0446	0.078*
H17B	0.6530	1.2893	0.0840	0.078*
C18	0.8115 (3)	1.1790 (2)	0.09202 (7)	0.0519 (7)
H18	0.8675	1.2503	0.0937	0.062*
C19	0.7832 (2)	1.2475 (2)	0.15886 (7)	0.0437 (7)
C20	0.6480 (3)	1.3493 (3)	0.20374 (9)	0.0622 (8)
C21	0.4802 (2)	1.4741 (2)	0.17330 (7)	0.0993 (11)
H21A	0.4312	1.4634	0.1947	0.149*
H21B	0.4232	1.4787	0.1494	0.149*
H21C	0.5291	1.5476	0.1769	0.149*
O1'	1.03091 (19)	0.76936 (14)	−0.01426 (5)	0.0886 (6)
H1'	1.0588	0.8226	−0.0274	0.133*
O2'	0.76767 (14)	0.85390 (13)	0.06008 (4)	0.0528 (5)
O3'	0.49646 (19)	0.72222 (18)	0.09809 (6)	0.1029 (8)
O4'	0.50770 (17)	0.78587 (15)	0.03792 (5)	0.0634 (5)
C1'	0.8707 (2)	0.7051 (2)	0.02422 (7)	0.0455 (7)
C2'	0.9863 (2)	0.6509 (2)	0.05104 (7)	0.0674 (8)
H2'1	0.9539	0.5878	0.0668	0.081*
H2'2	1.0430	0.6124	0.0346	0.081*
C3'	1.0657 (3)	0.7376 (2)	0.07821 (8)	0.0805 (9)
H3'1	1.0092	0.7837	0.0928	0.097*
H3'2	1.1095	0.7941	0.0629	0.097*
C4'	1.1648 (3)	0.6705 (4)	0.10664 (10)	0.1179 (13)
H4'1	1.1364	0.5870	0.1072	0.141*	0.50
H4'2	1.2441	0.6701	0.0950	0.141*	0.50
H4'3	1.1863	0.5945	0.0950	0.141*	0.50
H4'4	1.2424	0.7187	0.1110	0.141*	0.50
C5'A	1.1960 (7)	0.7055 (9)	0.1448 (4)	0.099 (3)	0.50
H5'A	1.2492	0.7774	0.1454	0.119*	0.50
H5'B	1.2469	0.6419	0.1586	0.119*	0.50
C6'	1.0719 (3)	0.7344 (3)	0.16847 (10)	0.0829 (10)
H6'1	1.1017	0.7620	0.1946	0.100*	0.50
H6'2	1.0198	0.7979	0.1552	0.100*	0.50
H6'3	1.0373	0.8005	0.1519	0.100*	0.50
H6'4	1.1451	0.7663	0.1852	0.100*	0.50
C7'A	0.9891 (7)	0.6152 (5)	0.17032 (19)	0.073 (2)	0.50
H7'A	0.9930	0.5683	0.1468	0.088*	0.50
H7'B	1.0252	0.5664	0.1923	0.088*	0.50
C8'	0.8520 (3)	0.6437 (2)	0.17439 (8)	0.0703 (8)
H8'1	0.8489	0.6985	0.1962	0.084*	0.50
H8'2	0.8082	0.5696	0.1801	0.084*	0.50
H8'3	0.7903	0.6362	0.1929	0.084*	0.50
H8'4	0.8748	0.5620	0.1675	0.084*	0.50
C5'	1.1191 (9)	0.6460 (9)	0.1439 (3)	0.098 (3)	0.50
H5'1	1.0514	0.5864	0.1387	0.118*	0.50
H5'2	1.1892	0.6056	0.1597	0.118*	0.50
C7'	0.9680 (7)	0.6993 (6)	0.19517 (16)	0.083 (2)	0.50
H7'1	1.0058	0.6432	0.2149	0.099*	0.50
H7'2	0.9434	0.7715	0.2084	0.099*	0.50
C9'	0.7812 (2)	0.70174 (19)	0.13731 (7)	0.0603 (8)
H9'1	0.7079	0.7467	0.1442	0.072*
H9'2	0.8382	0.7588	0.1268	0.072*
C10'	0.7351 (2)	0.60985 (18)	0.10600 (7)	0.0521 (7)
H10C	0.6708	0.5593	0.1159	0.063*
H10D	0.8069	0.5580	0.1021	0.063*
C11'	0.6776 (2)	0.6595 (2)	0.06578 (7)	0.0405 (6)
C12'	0.6397 (2)	0.55262 (19)	0.03790 (7)	0.0604 (8)
H12C	0.6075	0.4871	0.0527	0.072*
H12D	0.5706	0.5784	0.0185	0.072*
C13'	0.7493 (3)	0.5048 (2)	0.01722 (7)	0.0727 (9)
H13C	0.7170	0.4427	−0.0013	0.087*
H13D	0.8137	0.4682	0.0362	0.087*
C14'	0.8110 (3)	0.6062 (2)	−0.00432 (8)	0.0618 (8)
H14'	0.8813	0.5699	−0.0165	0.074*
C15'	0.7152 (3)	0.6575 (2)	−0.03696 (7)	0.0822 (9)
H15C	0.6859	0.5929	−0.0549	0.099*
H15D	0.6413	0.6887	−0.0259	0.099*
C16'	0.7727 (3)	0.7582 (3)	−0.05933 (7)	0.0875 (10)
H16C	0.8436	0.7267	−0.0718	0.105*
H16D	0.7084	0.7895	−0.0794	0.105*
C17'	0.8197 (2)	0.8587 (2)	−0.03123 (8)	0.0736 (9)
H17C	0.7475	0.8926	−0.0200	0.088*
H17D	0.8573	0.9226	−0.0454	0.088*
C18'	0.9190 (2)	0.8128 (2)	0.00130 (7)	0.0576 (8)
H18'	0.9437	0.8794	0.0194	0.069*
C19'	0.7713 (2)	0.7487 (2)	0.04983 (6)	0.0416 (7)
C20'	0.5537 (3)	0.7261 (2)	0.07042 (9)	0.0559 (8)
C21'	0.3860 (2)	0.8470 (2)	0.03813 (6)	0.0781 (9)
H21D	0.3178	0.7886	0.0350	0.117*
H21E	0.3743	0.9041	0.0171	0.117*
H21F	0.3850	0.8888	0.0624	0.117*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0928 (16)	0.0468 (12)	0.0668 (13)	−0.0187 (10)	0.0446 (11)	−0.0158 (10)
O2	0.0859 (15)	0.0369 (11)	0.0563 (12)	−0.0075 (10)	0.0204 (10)	−0.0002 (10)
O3	0.1239 (19)	0.0902 (16)	0.0727 (16)	0.0196 (12)	0.0232 (14)	−0.0348 (12)
O4	0.0793 (16)	0.0708 (14)	0.0789 (15)	0.0305 (11)	0.0124 (12)	−0.0036 (12)
C1	0.048 (2)	0.0300 (16)	0.0393 (17)	0.0001 (14)	0.0145 (14)	0.0001 (14)
C2	0.050 (2)	0.0537 (18)	0.067 (2)	0.0047 (16)	0.0170 (16)	0.0008 (14)
C3	0.055 (2)	0.079 (2)	0.104 (2)	−0.0027 (19)	0.0107 (19)	−0.0096 (18)
C4	0.045 (2)	0.106 (3)	0.177 (4)	0.002 (2)	0.005 (2)	−0.018 (2)
C5	0.082 (3)	0.148 (4)	0.206 (5)	0.011 (3)	−0.005 (3)	0.010 (3)
C6	0.067 (3)	0.149 (4)	0.141 (4)	−0.034 (3)	−0.012 (2)	0.030 (3)
C7	0.088 (3)	0.131 (4)	0.135 (3)	−0.012 (3)	−0.034 (3)	0.033 (3)
C8	0.117 (3)	0.097 (3)	0.075 (2)	−0.012 (2)	−0.018 (2)	0.001 (2)
C9	0.088 (2)	0.061 (2)	0.064 (2)	−0.0088 (18)	0.0000 (18)	−0.0071 (16)
C10	0.076 (2)	0.065 (2)	0.0421 (18)	−0.0054 (17)	0.0091 (16)	0.0031 (15)
C11	0.059 (2)	0.0371 (17)	0.0397 (18)	0.0022 (16)	0.0145 (16)	0.0001 (14)
C12	0.064 (2)	0.0575 (18)	0.0491 (18)	0.0001 (16)	0.0224 (15)	0.0049 (15)
C13	0.060 (2)	0.0435 (17)	0.0519 (19)	−0.0080 (13)	0.0169 (15)	0.0053 (15)
C14	0.055 (2)	0.0360 (16)	0.0416 (18)	0.0036 (15)	0.0145 (15)	0.0020 (13)
C15	0.061 (2)	0.0634 (19)	0.058 (2)	0.0003 (15)	0.0104 (17)	−0.0011 (16)
C16	0.075 (2)	0.072 (2)	0.051 (2)	0.0085 (17)	−0.0031 (16)	0.0051 (16)
C17	0.104 (3)	0.0474 (19)	0.0442 (19)	0.0026 (18)	0.0119 (18)	0.0073 (14)
C18	0.078 (2)	0.0342 (17)	0.047 (2)	−0.0057 (15)	0.0226 (17)	−0.0022 (14)
C19	0.0468 (19)	0.0398 (18)	0.0441 (19)	0.0014 (15)	0.0041 (14)	0.0032 (16)
C20	0.075 (2)	0.057 (2)	0.058 (2)	−0.0012 (19)	0.021 (2)	−0.0015 (19)
C21	0.093 (3)	0.082 (2)	0.129 (3)	0.048 (2)	0.037 (2)	0.0126 (19)
O1'	0.0798 (16)	0.0967 (16)	0.1013 (17)	0.0306 (13)	0.0589 (12)	0.0360 (12)
O2'	0.0603 (13)	0.0354 (11)	0.0669 (13)	−0.0010 (10)	0.0252 (9)	−0.0036 (9)
O3'	0.0673 (17)	0.168 (2)	0.0803 (16)	0.0303 (13)	0.0357 (13)	0.0384 (15)
O4'	0.0572 (14)	0.0752 (14)	0.0592 (14)	0.0170 (10)	0.0131 (11)	0.0051 (11)
C1'	0.053 (2)	0.0343 (17)	0.0523 (19)	0.0092 (14)	0.0209 (17)	0.0054 (15)
C2'	0.058 (2)	0.067 (2)	0.080 (2)	0.0239 (17)	0.0225 (18)	0.0259 (18)
C3'	0.057 (2)	0.111 (3)	0.074 (2)	0.0177 (19)	0.0124 (18)	0.014 (2)
C4'	0.068 (3)	0.188 (4)	0.096 (3)	0.030 (2)	0.001 (3)	0.027 (4)
C5'A	0.044 (6)	0.115 (7)	0.137 (9)	0.019 (4)	0.006 (6)	−0.029 (6)
C6'	0.082 (3)	0.075 (3)	0.085 (3)	0.000 (2)	−0.016 (2)	0.014 (2)
C7'A	0.089 (6)	0.067 (5)	0.061 (5)	0.034 (4)	0.003 (4)	0.009 (4)
C8'	0.096 (3)	0.065 (2)	0.050 (2)	−0.003 (2)	0.010 (2)	0.0012 (17)
C5'	0.084 (8)	0.129 (9)	0.080 (7)	0.060 (6)	0.008 (7)	0.051 (7)
C7'	0.110 (7)	0.071 (5)	0.065 (5)	−0.012 (5)	0.001 (5)	0.024 (4)
C9'	0.073 (2)	0.0569 (19)	0.0519 (19)	0.0035 (15)	0.0107 (16)	0.0049 (16)
C10'	0.062 (2)	0.0455 (17)	0.0504 (19)	−0.0021 (14)	0.0126 (15)	0.0053 (15)
C11'	0.0454 (19)	0.0322 (16)	0.0462 (18)	−0.0013 (15)	0.0144 (15)	−0.0017 (14)
C12'	0.076 (2)	0.0411 (18)	0.065 (2)	−0.0067 (15)	0.0136 (17)	0.0004 (15)
C13'	0.101 (3)	0.0431 (19)	0.075 (2)	0.0019 (18)	0.0127 (19)	−0.0112 (17)
C14'	0.081 (2)	0.045 (2)	0.065 (2)	0.0157 (17)	0.0282 (18)	−0.0012 (17)
C15'	0.114 (3)	0.078 (2)	0.056 (2)	0.004 (2)	0.018 (2)	−0.0047 (18)
C16'	0.109 (3)	0.102 (3)	0.055 (2)	0.018 (2)	0.025 (2)	0.018 (2)
C17'	0.080 (2)	0.071 (2)	0.074 (2)	0.0201 (18)	0.0276 (19)	0.0303 (19)
C18'	0.055 (2)	0.058 (2)	0.066 (2)	0.0144 (16)	0.0352 (18)	0.0132 (16)
C19'	0.0441 (19)	0.0375 (17)	0.0426 (18)	0.0067 (17)	0.0034 (14)	0.0040 (15)
C20'	0.053 (2)	0.057 (2)	0.058 (2)	−0.0078 (18)	0.0107 (19)	0.0056 (18)
C21'	0.054 (2)	0.093 (2)	0.085 (2)	0.0178 (17)	0.0007 (17)	−0.0073 (17)

Geometric parameters (Å, º)

O1—C18	1.439 (2)	C1'—C18'	1.550 (3)
O1—H1	0.8200	C1'—C14'	1.552 (3)
O2—C19	1.219 (2)	C1'—C2'	1.554 (3)
O3—C20	1.188 (2)	C2'—C3'	1.518 (3)
O4—C20	1.341 (3)	C2'—H2'1	0.9700
O4—C21	1.451 (2)	C2'—H2'2	0.9700
C1—C19	1.530 (3)	C3'—C4'	1.532 (3)
C1—C14	1.538 (3)	C3'—H3'1	0.9700
C1—C18	1.544 (3)	C3'—H3'2	0.9700
C1—C2	1.548 (3)	C4'—C5'A	1.377 (10)
C2—C3	1.511 (3)	C4'—C5'	1.456 (9)
C2—H2A	0.9700	C4'—H4'1	0.9700
C2—H2B	0.9700	C4'—H4'2	0.9700
C3—C4	1.528 (3)	C4'—H4'3	0.9700
C3—H3A	0.9700	C4'—H4'4	0.9700
C3—H3B	0.9700	C5'A—C6'	1.652 (11)
C4—C5	1.483 (3)	C5'A—H5'A	0.9700
C4—H4A	0.9700	C5'A—H5'B	0.9700
C4—H4B	0.9700	C6'—C5'	1.422 (10)
C5—C6	1.528 (4)	C6'—C7'	1.563 (7)
C5—H5A	0.9700	C6'—C7'A	1.583 (7)
C5—H5B	0.9700	C6'—H6'1	0.9700
C6—C7	1.559 (4)	C6'—H6'2	0.9700
C6—H6A	0.9700	C6'—H6'3	0.9700
C6—H6B	0.9700	C6'—H6'4	0.9700
C7—C8	1.537 (3)	C7'A—C8'	1.498 (6)
C7—H7A	0.9700	C7'A—H7'A	0.9700
C7—H7B	0.9700	C7'A—H7'B	0.9700
C8—C9	1.544 (3)	C8'—C7'	1.471 (6)
C8—H8A	0.9700	C8'—C9'	1.541 (3)
C8—H8B	0.9700	C8'—H8'1	0.9700
C9—C10	1.532 (3)	C8'—H8'2	0.9700
C9—H9A	0.9700	C8'—H8'3	0.9700
C9—H9B	0.9700	C8'—H8'4	0.9700
C10—C11	1.544 (3)	C5'—H5'1	0.9700
C10—H10A	0.9700	C5'—H5'2	0.9700
C10—H10B	0.9700	C7'—H7'1	0.9700
C11—C20	1.536 (3)	C7'—H7'2	0.9700
C11—C19	1.540 (3)	C9'—C10'	1.520 (2)
C11—C12	1.551 (3)	C9'—H9'1	0.9700
C12—C13	1.524 (2)	C9'—H9'2	0.9700
C12—H12A	0.9700	C10'—C11'	1.547 (2)
C12—H12B	0.9700	C10'—H10C	0.9700
C13—C14	1.536 (2)	C10'—H10D	0.9700
C13—H13A	0.9700	C11'—C20'	1.520 (3)
C13—H13B	0.9700	C11'—C19'	1.542 (3)
C14—C15	1.539 (3)	C11'—C12'	1.545 (3)
C14—H14	0.9800	C12'—C13'	1.523 (3)
C15—C16	1.522 (2)	C12'—H12C	0.9700
C15—H15A	0.9700	C12'—H12D	0.9700
C15—H15B	0.9700	C13'—C14'	1.533 (3)
C16—C17	1.520 (3)	C13'—H13C	0.9700
C16—H16A	0.9700	C13'—H13D	0.9700
C16—H16B	0.9700	C14'—C15'	1.526 (3)
C17—C18	1.520 (3)	C14'—H14'	0.9800
C17—H17A	0.9700	C15'—C16'	1.521 (3)
C17—H17B	0.9700	C15'—H15C	0.9700
C18—H18	0.9800	C15'—H15D	0.9700
C21—H21A	0.9600	C16'—C17'	1.518 (3)
C21—H21B	0.9600	C16'—H16C	0.9700
C21—H21C	0.9600	C16'—H16D	0.9700
O1'—C18'	1.435 (2)	C17'—C18'	1.523 (3)
O1'—H1'	0.8200	C17'—H17C	0.9700
O2'—C19'	1.216 (2)	C17'—H17D	0.9700
O3'—C20'	1.192 (3)	C18'—H18'	0.9800
O4'—C20'	1.342 (3)	C21'—H21D	0.9600
O4'—C21'	1.447 (2)	C21'—H21E	0.9600
C1'—C19'	1.528 (3)	C21'—H21F	0.9600
C18—O1—H1	109.5	C5'—C4'—H4'3	109.0
C20—O4—C21	116.8 (2)	C3'—C4'—H4'3	109.0
C19—C1—C14	110.4 (2)	H4'2—C4'—H4'3	64.3
C19—C1—C18	107.85 (18)	C5'A—C4'—H4'4	66.4
C14—C1—C18	111.49 (19)	C5'—C4'—H4'4	109.0
C19—C1—C2	108.88 (18)	C3'—C4'—H4'4	109.0
C14—C1—C2	109.37 (19)	H4'1—C4'—H4'4	140.6
C18—C1—C2	108.8 (2)	H4'2—C4'—H4'4	47.0
C3—C2—C1	117.2 (2)	H4'3—C4'—H4'4	107.8
C3—C2—H2A	108.0	C4'—C5'A—C6'	114.8 (5)
C1—C2—H2A	108.0	C4'—C5'A—H5'A	108.6
C3—C2—H2B	108.0	C6'—C5'A—H5'A	108.6
C1—C2—H2B	108.0	C4'—C5'A—H5'B	108.6
H2A—C2—H2B	107.2	C6'—C5'A—H5'B	108.6
C2—C3—C4	112.0 (2)	H5'A—C5'A—H5'B	107.5
C2—C3—H3A	109.2	C5'—C6'—C7'	120.1 (5)
C4—C3—H3A	109.2	C5'—C6'—C7'A	71.8 (5)
C2—C3—H3B	109.2	C7'—C6'—C7'A	48.9 (3)
C4—C3—H3B	109.2	C7'—C6'—C5'A	153.5 (5)
H3A—C3—H3B	107.9	C7'A—C6'—C5'A	109.3 (5)
C5—C4—C3	116.4 (3)	C5'—C6'—H6'1	132.6
C5—C4—H4A	108.2	C7'—C6'—H6'1	72.2
C3—C4—H4A	108.2	C7'A—C6'—H6'1	109.8
C5—C4—H4B	108.2	C5'A—C6'—H6'1	109.8
C3—C4—H4B	108.2	C5'—C6'—H6'2	115.6
H4A—C4—H4B	107.3	C7'—C6'—H6'2	93.7
C4—C5—C6	118.2 (3)	C7'A—C6'—H6'2	109.8
C4—C5—H5A	107.8	C5'A—C6'—H6'2	109.8
C6—C5—H5A	107.8	H6'1—C6'—H6'2	108.3
C4—C5—H5B	107.8	C5'—C6'—H6'3	107.3
C6—C5—H5B	107.8	C7'—C6'—H6'3	107.3
H5A—C5—H5B	107.1	C7'A—C6'—H6'3	118.8
C5—C6—C7	110.9 (3)	C5'A—C6'—H6'3	96.6
C5—C6—H6A	109.5	H6'1—C6'—H6'3	111.6
C7—C6—H6A	109.5	C5'—C6'—H6'4	107.3
C5—C6—H6B	109.5	C7'—C6'—H6'4	107.3
C7—C6—H6B	109.5	C7'A—C6'—H6'4	132.6
H6A—C6—H6B	108.0	C5'A—C6'—H6'4	75.5
C8—C7—C6	111.5 (3)	H6'2—C6'—H6'4	112.3
C8—C7—H7A	109.3	H6'3—C6'—H6'4	106.9
C6—C7—H7A	109.3	C8'—C7'A—C6'	111.7 (4)
C8—C7—H7B	109.3	C8'—C7'A—H7'A	109.3
C6—C7—H7B	109.3	C6'—C7'A—H7'A	109.3
H7A—C7—H7B	108.0	C8'—C7'A—H7'B	109.3
C7—C8—C9	111.4 (2)	C6'—C7'A—H7'B	109.3
C7—C8—H8A	109.4	H7'A—C7'A—H7'B	107.9
C9—C8—H8A	109.4	C7'—C8'—C7'A	52.0 (3)
C7—C8—H8B	109.4	C7'—C8'—C9'	121.3 (3)
C9—C8—H8B	109.4	C7'A—C8'—C9'	112.4 (3)
H8A—C8—H8B	108.0	C7'—C8'—H8'1	57.6
C10—C9—C8	112.8 (2)	C7'A—C8'—H8'1	109.1
C10—C9—H9A	109.0	C9'—C8'—H8'1	109.1
C8—C9—H9A	109.0	C7'—C8'—H8'2	129.6
C10—C9—H9B	109.0	C7'A—C8'—H8'2	109.1
C8—C9—H9B	109.0	C9'—C8'—H8'2	109.1
H9A—C9—H9B	107.8	H8'1—C8'—H8'2	107.9
C9—C10—C11	117.5 (2)	C7'—C8'—H8'3	107.0
C9—C10—H10A	107.9	C7'A—C8'—H8'3	140.6
C11—C10—H10A	107.9	C9'—C8'—H8'3	107.0
C9—C10—H10B	107.9	H8'1—C8'—H8'3	56.7
C11—C10—H10B	107.9	H8'2—C8'—H8'3	54.7
H10A—C10—H10B	107.2	C7'—C8'—H8'4	107.0
C20—C11—C19	108.4 (2)	C7'A—C8'—H8'4	60.8
C20—C11—C10	109.3 (2)	C9'—C8'—H8'4	107.0
C19—C11—C10	110.7 (2)	H8'1—C8'—H8'4	143.4
C20—C11—C12	105.7 (2)	H8'2—C8'—H8'4	53.4
C19—C11—C12	113.49 (19)	H8'3—C8'—H8'4	106.8
C10—C11—C12	108.98 (19)	C6'—C5'—C4'	125.3 (7)
C13—C12—C11	114.42 (19)	C6'—C5'—H5'1	106.0
C13—C12—H12A	108.7	C4'—C5'—H5'1	106.0
C11—C12—H12A	108.7	C6'—C5'—H5'2	106.0
C13—C12—H12B	108.7	C4'—C5'—H5'2	106.0
C11—C12—H12B	108.7	H5'1—C5'—H5'2	106.3
H12A—C12—H12B	107.6	C8'—C7'—C6'	114.3 (4)
C12—C13—C14	111.70 (17)	C8'—C7'—H7'1	108.7
C12—C13—H13A	109.3	C6'—C7'—H7'1	108.7
C14—C13—H13A	109.3	C8'—C7'—H7'2	108.7
C12—C13—H13B	109.3	C6'—C7'—H7'2	108.7
C14—C13—H13B	109.3	H7'1—C7'—H7'2	107.6
H13A—C13—H13B	107.9	C10'—C9'—C8'	113.2 (2)
C13—C14—C1	111.18 (18)	C10'—C9'—H9'1	108.9
C13—C14—C15	110.4 (2)	C8'—C9'—H9'1	108.9
C1—C14—C15	113.16 (18)	C10'—C9'—H9'2	108.9
C13—C14—H14	107.3	C8'—C9'—H9'2	108.9
C1—C14—H14	107.3	H9'1—C9'—H9'2	107.7
C15—C14—H14	107.3	C9'—C10'—C11'	117.33 (18)
C16—C15—C14	111.5 (2)	C9'—C10'—H10C	108.0
C16—C15—H15A	109.3	C11'—C10'—H10C	108.0
C14—C15—H15A	109.3	C9'—C10'—H10D	108.0
C16—C15—H15B	109.3	C11'—C10'—H10D	108.0
C14—C15—H15B	109.3	H10C—C10'—H10D	107.2
H15A—C15—H15B	108.0	C20'—C11'—C19'	108.7 (2)
C17—C16—C15	108.47 (19)	C20'—C11'—C12'	106.1 (2)
C17—C16—H16A	110.0	C19'—C11'—C12'	113.06 (19)
C15—C16—H16A	110.0	C20'—C11'—C10'	108.7 (2)
C17—C16—H16B	110.0	C19'—C11'—C10'	110.63 (19)
C15—C16—H16B	110.0	C12'—C11'—C10'	109.41 (18)
H16A—C16—H16B	108.4	C13'—C12'—C11'	114.0 (2)
C18—C17—C16	112.26 (19)	C13'—C12'—H12C	108.7
C18—C17—H17A	109.2	C11'—C12'—H12C	108.7
C16—C17—H17A	109.2	C13'—C12'—H12D	108.7
C18—C17—H17B	109.2	C11'—C12'—H12D	108.7
C16—C17—H17B	109.2	H12C—C12'—H12D	107.6
H17A—C17—H17B	107.9	C12'—C13'—C14'	111.34 (19)
O1—C18—C17	110.0 (2)	C12'—C13'—H13C	109.4
O1—C18—C1	112.44 (19)	C14'—C13'—H13C	109.4
C17—C18—C1	112.5 (2)	C12'—C13'—H13D	109.4
O1—C18—H18	107.2	C14'—C13'—H13D	109.4
C17—C18—H18	107.2	H13C—C13'—H13D	108.0
C1—C18—H18	107.2	C15'—C14'—C13'	110.5 (2)
O2—C19—C1	120.7 (2)	C15'—C14'—C1'	112.8 (2)
O2—C19—C11	117.8 (2)	C13'—C14'—C1'	111.5 (2)
C1—C19—C11	121.3 (2)	C15'—C14'—H14'	107.2
O3—C20—O4	123.0 (3)	C13'—C14'—H14'	107.2
O3—C20—C11	126.1 (3)	C1'—C14'—H14'	107.2
O4—C20—C11	110.8 (2)	C16'—C15'—C14'	112.4 (2)
O4—C21—H21A	109.5	C16'—C15'—H15C	109.1
O4—C21—H21B	109.5	C14'—C15'—H15C	109.1
H21A—C21—H21B	109.5	C16'—C15'—H15D	109.1
O4—C21—H21C	109.5	C14'—C15'—H15D	109.1
H21A—C21—H21C	109.5	H15C—C15'—H15D	107.9
H21B—C21—H21C	109.5	C17'—C16'—C15'	109.1 (2)
C18'—O1'—H1'	109.5	C17'—C16'—H16C	109.9
C20'—O4'—C21'	116.9 (2)	C15'—C16'—H16C	109.9
C19'—C1'—C18'	110.10 (19)	C17'—C16'—H16D	109.9
C19'—C1'—C14'	109.9 (2)	C15'—C16'—H16D	109.9
C18'—C1'—C14'	110.3 (2)	H16C—C16'—H16D	108.3
C19'—C1'—C2'	108.34 (19)	C16'—C17'—C18'	111.7 (2)
C18'—C1'—C2'	108.7 (2)	C16'—C17'—H17C	109.3
C14'—C1'—C2'	109.5 (2)	C18'—C17'—H17C	109.3
C3'—C2'—C1'	117.1 (2)	C16'—C17'—H17D	109.3
C3'—C2'—H2'1	108.0	C18'—C17'—H17D	109.3
C1'—C2'—H2'1	108.0	H17C—C17'—H17D	108.0
C3'—C2'—H2'2	108.0	O1'—C18'—C17'	110.6 (2)
C1'—C2'—H2'2	108.0	O1'—C18'—C1'	105.62 (18)
H2'1—C2'—H2'2	107.3	C17'—C18'—C1'	113.3 (2)
C2'—C3'—C4'	111.7 (3)	O1'—C18'—H18'	109.0
C2'—C3'—H3'1	109.3	C17'—C18'—H18'	109.0
C4'—C3'—H3'1	109.3	C1'—C18'—H18'	109.0
C2'—C3'—H3'2	109.3	O2'—C19'—C1'	121.2 (2)
C4'—C3'—H3'2	109.3	O2'—C19'—C11'	117.5 (2)
H3'1—C3'—H3'2	107.9	C1'—C19'—C11'	121.1 (2)
C5'A—C4'—C3'	122.9 (5)	O3'—C20'—O4'	121.7 (3)
C5'—C4'—C3'	112.7 (4)	O3'—C20'—C11'	126.2 (3)
C5'A—C4'—H4'1	106.6	O4'—C20'—C11'	112.0 (2)
C5'—C4'—H4'1	70.8	O4'—C21'—H21D	109.5
C3'—C4'—H4'1	106.6	O4'—C21'—H21E	109.5
C5'A—C4'—H4'2	106.6	H21D—C21'—H21E	109.5
C5'—C4'—H4'2	139.6	O4'—C21'—H21F	109.5
C3'—C4'—H4'2	106.6	H21D—C21'—H21F	109.5
H4'1—C4'—H4'2	106.6	H21E—C21'—H21F	109.5
C5'A—C4'—H4'3	127.0
C19—C1—C2—C3	−62.8 (3)	C4'—C5'A—C6'—C7'	92.9 (13)
C14—C1—C2—C3	176.5 (2)	C4'—C5'A—C6'—C7'A	62.2 (9)
C18—C1—C2—C3	54.5 (3)	C5'—C6'—C7'A—C8'	−145.2 (6)
C1—C2—C3—C4	172.9 (2)	C7'—C6'—C7'A—C8'	43.2 (4)
C2—C3—C4—C5	−143.3 (3)	C5'A—C6'—C7'A—C8'	−154.4 (5)
C3—C4—C5—C6	47.7 (5)	C6'—C7'A—C8'—C7'	−44.1 (4)
C4—C5—C6—C7	55.7 (4)	C6'—C7'A—C8'—C9'	68.9 (5)
C5—C6—C7—C8	−158.7 (3)	C7'—C6'—C5'—C4'	149.7 (8)
C6—C7—C8—C9	75.5 (3)	C7'A—C6'—C5'—C4'	142.4 (10)
C7—C8—C9—C10	74.5 (3)	C5'A—C6'—C5'—C4'	−51.6 (7)
C8—C9—C10—C11	−168.8 (2)	C5'A—C4'—C5'—C6'	59.5 (10)
C9—C10—C11—C20	−64.3 (3)	C3'—C4'—C5'—C6'	−55.0 (12)
C9—C10—C11—C19	55.1 (3)	C7'A—C8'—C7'—C6'	45.9 (4)
C9—C10—C11—C12	−179.4 (2)	C9'—C8'—C7'—C6'	−49.3 (7)
C20—C11—C12—C13	154.0 (2)	C5'—C6'—C7'—C8'	−54.6 (7)
C19—C11—C12—C13	35.2 (3)	C7'A—C6'—C7'—C8'	−45.3 (4)
C10—C11—C12—C13	−88.6 (2)	C5'A—C6'—C7'—C8'	−85.1 (11)
C11—C12—C13—C14	−52.6 (3)	C7'—C8'—C9'—C10'	139.2 (5)
C12—C13—C14—C1	62.1 (3)	C7'A—C8'—C9'—C10'	81.1 (4)
C12—C13—C14—C15	−64.3 (2)	C8'—C9'—C10'—C11'	−172.7 (2)
C19—C1—C14—C13	−52.9 (2)	C9'—C10'—C11'—C20'	−65.9 (3)
C18—C1—C14—C13	−172.73 (18)	C9'—C10'—C11'—C19'	53.4 (3)
C2—C1—C14—C13	66.9 (2)	C9'—C10'—C11'—C12'	178.63 (19)
C19—C1—C14—C15	72.0 (2)	C20'—C11'—C12'—C13'	157.5 (2)
C18—C1—C14—C15	−47.8 (3)	C19'—C11'—C12'—C13'	38.4 (3)
C2—C1—C14—C15	−168.21 (18)	C10'—C11'—C12'—C13'	−85.3 (2)
C13—C14—C15—C16	179.56 (17)	C11'—C12'—C13'—C14'	−54.4 (3)
C1—C14—C15—C16	54.2 (3)	C12'—C13'—C14'—C15'	−64.4 (3)
C14—C15—C16—C17	−58.7 (3)	C12'—C13'—C14'—C1'	62.0 (3)
C15—C16—C17—C18	60.0 (3)	C19'—C1'—C14'—C15'	72.9 (3)
C16—C17—C18—O1	70.5 (3)	C18'—C1'—C14'—C15'	−48.7 (3)
C16—C17—C18—C1	−55.7 (3)	C2'—C1'—C14'—C15'	−168.3 (2)
C19—C1—C18—O1	162.07 (19)	C19'—C1'—C14'—C13'	−52.3 (3)
C14—C1—C18—O1	−76.6 (3)	C18'—C1'—C14'—C13'	−173.8 (2)
C2—C1—C18—O1	44.1 (3)	C2'—C1'—C14'—C13'	66.6 (3)
C19—C1—C18—C17	−73.0 (2)	C13'—C14'—C15'—C16'	−179.6 (2)
C14—C1—C18—C17	48.3 (3)	C1'—C14'—C15'—C16'	54.7 (3)
C2—C1—C18—C17	169.01 (18)	C14'—C15'—C16'—C17'	−58.3 (3)
C14—C1—C19—O2	−147.3 (2)	C15'—C16'—C17'—C18'	58.3 (3)
C18—C1—C19—O2	−25.3 (3)	C16'—C17'—C18'—O1'	62.8 (3)
C2—C1—C19—O2	92.6 (3)	C16'—C17'—C18'—C1'	−55.6 (3)
C14—C1—C19—C11	38.4 (3)	C19'—C1'—C18'—O1'	166.8 (2)
C18—C1—C19—C11	160.4 (2)	C14'—C1'—C18'—O1'	−71.8 (2)
C2—C1—C19—C11	−81.7 (3)	C2'—C1'—C18'—O1'	48.3 (2)
C20—C11—C19—O2	38.9 (3)	C19'—C1'—C18'—C17'	−72.0 (3)
C10—C11—C19—O2	−81.1 (3)	C14'—C1'—C18'—C17'	49.5 (3)
C12—C11—C19—O2	156.0 (2)	C2'—C1'—C18'—C17'	169.5 (2)
C20—C11—C19—C1	−146.7 (2)	C18'—C1'—C19'—O2'	−23.0 (3)
C10—C11—C19—C1	93.4 (2)	C14'—C1'—C19'—O2'	−144.7 (2)
C12—C11—C19—C1	−29.5 (3)	C2'—C1'—C19'—O2'	95.7 (2)
C21—O4—C20—O3	0.3 (4)	C18'—C1'—C19'—C11'	160.9 (2)
C21—O4—C20—C11	177.6 (2)	C14'—C1'—C19'—C11'	39.2 (3)
C19—C11—C20—O3	−134.7 (3)	C2'—C1'—C19'—C11'	−80.3 (3)
C10—C11—C20—O3	−13.9 (4)	C20'—C11'—C19'—O2'	33.7 (3)
C12—C11—C20—O3	103.3 (3)	C12'—C11'—C19'—O2'	151.3 (2)
C19—C11—C20—O4	48.2 (3)	C10'—C11'—C19'—O2'	−85.6 (3)
C10—C11—C20—O4	168.9 (2)	C20'—C11'—C19'—C1'	−150.1 (2)
C12—C11—C20—O4	−73.9 (3)	C12'—C11'—C19'—C1'	−32.5 (3)
C19'—C1'—C2'—C3'	−66.3 (3)	C10'—C11'—C19'—C1'	90.6 (2)
C18'—C1'—C2'—C3'	53.3 (3)	C21'—O4'—C20'—O3'	0.8 (4)
C14'—C1'—C2'—C3'	173.9 (2)	C21'—O4'—C20'—C11'	176.53 (19)
C1'—C2'—C3'—C4'	172.5 (2)	C19'—C11'—C20'—O3'	−133.6 (3)
C2'—C3'—C4'—C5'A	−142.4 (7)	C12'—C11'—C20'—O3'	104.5 (3)
C2'—C3'—C4'—C5'	−94.9 (7)	C10'—C11'—C20'—O3'	−13.1 (4)
C5'—C4'—C5'A—C6'	−41.8 (6)	C19'—C11'—C20'—O4'	50.8 (3)
C3'—C4'—C5'A—C6'	47.1 (11)	C12'—C11'—C20'—O4'	−71.1 (2)
C4'—C5'A—C6'—C5'	48.1 (6)	C10'—C11'—C20'—O4'	171.34 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2′	0.82	2.02	2.816 (2)	163
O1′—H1′···O1^i	0.82	1.97	2.764 (2)	163

Symmetry code: (i) −x+2, −y+2, −z.