(S)-Methyl 6,7,8,9,10,11-hexahydro-1,6-dimethyl-10,11-dioxophenanthro[1,2-b]furan-6-carboxyl­ate (methyl tashinona­te)

The approximately planar mol­ecules of methyl tanshinonate, C₂₀H₁₈O₅, are stacked over each other along the b axis of the monoclinic unit cell. There are two independent molecules in the asymmetric unit.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.037
• wR factor = 0.107
• Data-to-parameter ratio = 7.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT369_ALERT_2_B Long   C(sp2)-C(sp2) Bond  C6     -   C7     ...       1.57 Ang.
PLAT369_ALERT_2_B Long   C(sp2)-C(sp2) Bond  C6'    -   C7'    ...       1.57 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.87
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.84 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
PLAT333_ALERT_2_C Large Average Benzene C-C Dist.  C4     -C9            1.45 Ang.
PLAT333_ALERT_2_C Large Average Benzene C-C Dist.  C4'    -C9'           1.45 Ang.
PLAT335_ALERT_2_C Large Benzene C-C Range          C4     -C9            0.22 Ang.
PLAT335_ALERT_2_C Large Benzene C-C Range          C4'    -C9'           0.21 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.10
           From the CIF: _reflns_number_total               3603
           Count of symmetry unique reflns         3720
           Completeness (_total/calc)             96.85%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   8 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
   8 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

(S)-Methyl 6,7,8,9,10,11-Hexahydro-1,6-dimethyl-10,11-dioxophenanthro[1,2-b]- furan-6-carboxylate

Crystal data

C20H18O5	F(000) = 712
Mr = 338.34	Dx = 1.393 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 853 reflections
a = 9.184 (1) Å	θ = 2.2–27.1°
b = 13.384 (2) Å	µ = 0.10 mm^−1
c = 13.638 (2) Å	T = 295 K
β = 105.720 (2)°	Block, red
V = 1613.7 (4) Å^3	0.48 × 0.41 × 0.34 mm
Z = 4

Data collection

Bruker SMART area-detector diffractometer	3071 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 27.1°, θmin = 2.2°
φ and ω scans	h = −11→8
8266 measured reflections	k = −16→17
3603 independent reflections	l = −14→17

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0661P)^2 + 0.2301P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.107	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.20 e Å^−3
3603 reflections	Δρmin = −0.22 e Å^−3
458 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.023 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Friedel pairs were merged
Secondary atom site location: difference Fourier map

Special details

Experimental. ¹H NMR (500 MHz, CDCl₃, TMS reference): δ 7.57 (d, J = 8 Hz, 1H), 7.49 (d, J = 8 Hz, 1H), 7.24 (q, J = 1 Hz, 1H), 3.68 (s, 3H), 3.25 (t, J = 6 Hz, 2H), 2.27 (d, J = 1 Hz, 1H), 1.81–1.84 (m, 2H), 1.74–1.78 (m, 2H), 1.60 (s, 3H). ¹³C NMR (500 MHz, CDCl₃, TMS reference): δ 183.4 (s), 128.6 (s), 175.6 (s), 161.3 (s), 144.4 (s), 143.1 (s), 141.6 (d), 134.9 (d), 128.6 (s), 126.6 (s), 121.6 (s), 120.2 (d), 52.4 (q), 47.2 (s), 34.1 (t), 29.0 (t), 27.6 (q), 19.2 (t), 8.7 (q). IR: 3433, 3121, 2953, 1726, 1665, 1581, 1533, 1463, 1337, 1244, 1167, 1110, 993, 915, 827, 791 cm^-1.

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

	x	y	z	Uiso*/Ueq
O1	−0.2895 (2)	0.5000 (2)	0.4758 (1)	0.0429 (4)
O2	0.1785 (2)	0.5016 (2)	0.7073 (2)	0.0496 (5)
O3	0.3144 (2)	0.4981 (2)	0.5581 (2)	0.0486 (5)
O4	0.0977 (4)	0.6218 (2)	0.1153 (2)	0.0764 (8)
O5	0.1701 (3)	0.5215 (2)	0.0097 (2)	0.0637 (7)
O1'	1.2741 (2)	0.7385 (2)	0.4800 (1)	0.0447 (5)
O2'	0.9938 (2)	0.7346 (2)	0.7124 (1)	0.0488 (5)
O3'	0.7370 (2)	0.7343 (2)	0.5626 (2)	0.0478 (5)
O4'	0.5828 (3)	0.5946 (2)	0.0980 (2)	0.0704 (7)
O5'	0.6708 (3)	0.7037 (2)	0.0057 (2)	0.0693 (7)
C1	−0.3097 (3)	0.5007 (2)	0.5728 (2)	0.0455 (6)
C2	−0.1783 (3)	0.5006 (2)	0.6451 (2)	0.0410 (6)
C3	−0.1528 (4)	0.5043 (3)	0.7580 (2)	0.0567 (8)
C4	−0.1381 (3)	0.4994 (2)	0.4891 (2)	0.0343 (5)
C5	−0.0643 (3)	0.5002 (2)	0.5897 (2)	0.0340 (5)
C6	0.0991 (3)	0.4993 (2)	0.6206 (2)	0.0344 (5)
C7	0.1781 (3)	0.4958 (2)	0.5318 (2)	0.0330 (5)
C8	0.0846 (2)	0.4894 (2)	0.4235 (2)	0.0302 (5)
C9	−0.0746 (2)	0.4941 (2)	0.4032 (2)	0.0309 (5)
C10	−0.1657 (3)	0.4930 (2)	0.3044 (2)	0.0387 (6)
C11	−0.1009 (3)	0.4800 (2)	0.2257 (2)	0.0392 (6)
C12	0.0545 (3)	0.4690 (2)	0.2418 (2)	0.0339 (5)
C13	0.1505 (3)	0.4783 (2)	0.3411 (2)	0.0322 (5)
C14	0.3206 (3)	0.4746 (2)	0.3603 (2)	0.0418 (6)
C15	0.3754 (3)	0.4625 (3)	0.2653 (2)	0.0515 (8)
C16	0.2712 (3)	0.3964 (3)	0.1879 (2)	0.0500 (7)
C17	0.1146 (3)	0.4445 (2)	0.1500 (2)	0.0411 (6)
C18	0.0096 (4)	0.3711 (3)	0.0767 (2)	0.0579 (8)
C19	0.1252 (3)	0.5403 (2)	0.0923 (2)	0.0392 (6)
C20	0.1917 (5)	0.6052 (3)	−0.0512 (2)	0.0622 (9)
C1'	1.3723 (3)	0.7374 (3)	0.5770 (2)	0.0488 (7)
C2'	1.2992 (3)	0.7372 (2)	0.6493 (2)	0.0432 (6)
C3'	1.3643 (4)	0.7345 (3)	0.7624 (2)	0.0637 (9)
C4'	1.1334 (3)	0.7394 (2)	0.4933 (2)	0.0348 (5)
C5'	1.1412 (3)	0.7384 (2)	0.5943 (2)	0.0352 (5)
C6'	1.0027 (3)	0.7384 (2)	0.6250 (2)	0.0340 (5)
C7'	0.8520 (3)	0.7408 (2)	0.5365 (2)	0.0338 (5)
C8'	0.8578 (2)	0.7482 (2)	0.4284 (2)	0.0310 (5)
C9'	1.0006 (3)	0.7435 (2)	0.4076 (2)	0.0318 (5)
C10'	1.0119 (3)	0.7441 (2)	0.3090 (2)	0.0384 (5)
C11'	0.8823 (3)	0.7508 (2)	0.2296 (2)	0.0408 (6)
C12'	0.7397 (3)	0.7581 (2)	0.2463 (2)	0.0351 (5)
C13'	0.7248 (3)	0.7573 (2)	0.3461 (2)	0.0324 (5)
C14'	0.5703 (3)	0.7686 (2)	0.3643 (2)	0.0425 (6)
C15'	0.4558 (3)	0.8145 (3)	0.2741 (2)	0.0520 (8)
C16'	0.4520 (3)	0.7582 (3)	0.1776 (2)	0.0525 (7)
C17'	0.6031 (3)	0.7676 (2)	0.1508 (2)	0.0409 (6)
C18'	0.6114 (4)	0.8675 (3)	0.0983 (3)	0.0562 (8)
C19'	0.6155 (3)	0.6781 (3)	0.0831 (2)	0.0494 (7)
C20'	0.6992 (6)	0.6233 (4)	−0.0559 (3)	0.088 (1)
H1	−0.4039	0.5011	0.5860	0.055*
H3a	−0.2472	0.4946	0.7742	0.085*
H3b	−0.1114	0.5681	0.7832	0.085*
H3c	−0.0833	0.4525	0.7893	0.085*
H10	−0.2698	0.5010	0.2914	0.046*
H11	−0.1630	0.4784	0.1594	0.047*
H14a	0.3593	0.4194	0.4060	0.050*
H14b	0.3631	0.5356	0.3947	0.050*
H15a	0.3814	0.5276	0.2354	0.062*
H15b	0.4762	0.4337	0.2840	0.062*
H16a	0.2620	0.3320	0.2183	0.060*
H16b	0.3134	0.3855	0.1308	0.060*
H18a	−0.0133	0.3157	0.1147	0.087*
H18b	0.0591	0.3472	0.0276	0.087*
H18c	−0.0824	0.4046	0.0422	0.087*
H20a	0.1952	0.5820	−0.1171	0.093*
H20b	0.2849	0.6382	−0.0183	0.093*
H20c	0.1092	0.6512	−0.0587	0.093*
H21	1.4771	0.7369	0.5902	0.059*
H23a	1.4724	0.7401	0.7785	0.096*
H23b	1.3379	0.6725	0.7885	0.096*
H23c	1.3244	0.7891	0.7928	0.096*
H30	1.1061	0.7399	0.2960	0.046*
H31	0.8903	0.7506	0.1631	0.049*
H34a	0.5790	0.8102	0.4238	0.051*
H34b	0.5345	0.7034	0.3784	0.051*
H35a	0.3563	0.8129	0.2860	0.062*
H35b	0.4821	0.8837	0.2668	0.062*
H36a	0.3713	0.7844	0.1221	0.063*
H36b	0.4309	0.6882	0.1864	0.063*
H38a	0.5975	0.9211	0.1417	0.084*
H38b	0.5334	0.8702	0.0351	0.084*
H38c	0.7085	0.8740	0.0851	0.084*
H40a	0.7226	0.6498	−0.1152	0.132*
H40b	0.6110	0.5817	−0.0764	0.132*
H40c	0.7831	0.5843	−0.0173	0.132*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.029 (1)	0.058 (1)	0.045 (1)	−0.002 (1)	0.016 (1)	−0.001 (1)
O2	0.045 (1)	0.065 (1)	0.037 (1)	0.003 (1)	0.008 (1)	−0.001 (1)
O3	0.031 (1)	0.069 (1)	0.045 (1)	0.001 (1)	0.008 (1)	−0.004 (1)
O4	0.128 (1)	0.047 (1)	0.080 (2)	0.012 (1)	0.072 (2)	0.007 (1)
O5	0.103 (2)	0.054 (1)	0.049 (1)	0.006 (1)	0.046 (1)	0.007 (1)
O1'	0.029 (1)	0.059 (1)	0.048 (1)	−0.002 (1)	0.012 (1)	0.003 (1)
O2'	0.053 (1)	0.060 (1)	0.036 (1)	0.000 (1)	0.016 (1)	−0.003 (1)
O3'	0.037 (1)	0.063 (1)	0.049 (1)	0.004 (1)	0.022 (1)	0.005 (1)
O4'	0.084 (2)	0.046 (1)	0.077 (2)	−0.005 (1)	0.013 (1)	−0.012 (1)
O5'	0.092 (2)	0.069 (2)	0.051 (1)	0.011 (1)	0.025 (1)	−0.009 (1)
C1	0.040 (1)	0.055 (2)	0.049 (2)	−0.008 (1)	0.026 (1)	−0.006 (2)
C2	0.046 (1)	0.039 (1)	0.045 (2)	−0.007 (1)	0.025 (1)	−0.007 (1)
C3	0.064 (2)	0.072 (2)	0.044 (2)	−0.019 (2)	0.031 (1)	−0.014 (2)
C4	0.030 (1)	0.033 (1)	0.043 (1)	−0.002 (1)	0.014 (1)	−0.003 (1)
C5	0.037 (1)	0.032 (1)	0.036 (1)	−0.001 (1)	0.016 (1)	−0.003 (1)
C6	0.038 (1)	0.030 (1)	0.036 (1)	0.001 (1)	0.012 (1)	−0.001 (1)
C7	0.032 (1)	0.032 (1)	0.036 (1)	0.002 (1)	0.011 (1)	0.001 (1)
C8	0.030 (1)	0.027 (1)	0.035 (1)	0.001 (1)	0.011 (1)	0.000 (1)
C9	0.029 (1)	0.031 (1)	0.035 (1)	0.001 (1)	0.011 (1)	0.000 (1)
C10	0.031 (1)	0.046 (2)	0.039 (1)	0.002 (1)	0.009 (1)	0.003 (1)
C11	0.040 (1)	0.045 (2)	0.031 (1)	0.001 (1)	0.007 (1)	0.002 (1)
C12	0.040 (1)	0.032 (1)	0.033 (1)	0.001 (1)	0.016 (1)	0.004 (1)
C13	0.033 (1)	0.028 (1)	0.039 (1)	0.001 (1)	0.015 (1)	0.002 (1)
C14	0.034 (1)	0.049 (2)	0.047 (2)	0.003 (1)	0.018 (1)	0.003 (1)
C15	0.040 (1)	0.071 (2)	0.050 (2)	0.011 (1)	0.025 (1)	0.012 (2)
C16	0.061 (2)	0.053 (2)	0.043 (2)	0.017 (1)	0.026 (1)	0.004 (1)
C17	0.049 (2)	0.043 (2)	0.037 (1)	0.003 (1)	0.020 (1)	0.001 (1)
C18	0.077 (2)	0.051 (2)	0.051 (2)	−0.010 (2)	0.026 (2)	−0.010 (2)
C19	0.041 (1)	0.045 (2)	0.033 (1)	0.002 (1)	0.013 (1)	−0.001 (1)
C20	0.086 (2)	0.065 (2)	0.042 (2)	−0.006 (2)	0.027 (2)	0.011 (2)
C1'	0.030 (1)	0.057 (2)	0.057 (2)	−0.004 (1)	0.007 (1)	0.007 (2)
C2'	0.035 (1)	0.043 (2)	0.048 (2)	−0.007 (1)	0.004 (1)	0.005 (1)
C3'	0.049 (2)	0.079 (2)	0.053 (2)	−0.012 (2)	−0.005 (1)	0.013 (2)
C4'	0.030 (1)	0.033 (1)	0.043 (1)	−0.002 (1)	0.013 (1)	0.000 (1)
C5'	0.036 (1)	0.033 (1)	0.037 (1)	−0.004 (1)	0.009 (1)	0.001 (1)
C6'	0.037 (1)	0.030 (1)	0.036 (1)	0.001 (1)	0.012 (1)	0.001 (1)
C7'	0.034 (1)	0.031 (1)	0.040 (1)	0.000 (1)	0.015 (1)	−0.002 (1)
C8'	0.030 (1)	0.029 (1)	0.036 (1)	0.000 (1)	0.012 (1)	0.000 (1)
C9'	0.030 (1)	0.031 (1)	0.036 (1)	−0.002 (1)	0.012 (1)	0.000 (1)
C10'	0.032 (1)	0.046 (1)	0.042 (1)	−0.003 (1)	0.017 (1)	−0.004 (1)
C11'	0.042 (1)	0.045 (2)	0.038 (1)	−0.002 (1)	0.017 (1)	−0.002 (1)
C12'	0.034 (1)	0.032 (1)	0.039 (1)	0.000 (1)	0.009 (1)	0.000 (1)
C13'	0.031 (1)	0.029 (1)	0.039 (1)	−0.001 (1)	0.013 (1)	−0.002 (1)
C14'	0.033 (1)	0.049 (2)	0.048 (2)	−0.001 (1)	0.015 (1)	0.000 (1)
C15'	0.035 (1)	0.065 (2)	0.056 (2)	0.006 (1)	0.011 (1)	−0.001 (2)
C16'	0.037 (1)	0.063 (2)	0.052 (2)	0.000 (1)	0.002 (1)	0.002 (2)
C17'	0.038 (1)	0.042 (2)	0.039 (1)	0.000 (1)	0.004 (1)	0.000 (1)
C18'	0.063 (2)	0.051 (2)	0.050 (2)	0.003 (2)	0.009 (1)	0.007 (2)
C19'	0.043 (2)	0.055 (2)	0.043 (2)	0.004 (1)	−0.002 (1)	−0.005 (1)
C20'	0.109 (3)	0.095 (3)	0.059 (2)	0.035 (3)	0.019 (2)	−0.017 (2)

Geometric parameters (Å, º)

O1—C4	1.353 (3)	C10'—C11'	1.377 (4)
O1—C1	1.385 (3)	C11'—C12'	1.391 (3)
O2—C6	1.211 (3)	C12'—C13'	1.404 (3)
O3—C7	1.206 (3)	C12'—C17'	1.550 (3)
O4—C19	1.182 (4)	C13'—C14'	1.513 (3)
O5—C19	1.324 (3)	C14'—C15'	1.515 (4)
O5—C20	1.440 (4)	C15'—C16'	1.509 (5)
O1'—C4'	1.352 (3)	C16'—C17'	1.534 (4)
O1'—C1'	1.384 (3)	C17'—C18'	1.528 (4)
O2'—C6'	1.219 (3)	C17'—C19'	1.535 (4)
O3'—C7'	1.206 (3)	C1—H1	0.93
O4'—C19'	1.189 (4)	C3—H3a	0.96
O5'—C19'	1.335 (4)	C3—H3b	0.96
O5'—C20'	1.432 (5)	C3—H3c	0.96
C1—C2	1.336 (4)	C10—H10	0.93
C2—C5	1.447 (3)	C11—H11	0.93
C2—C3	1.494 (4)	C14—H14a	0.97
C4—C5	1.357 (4)	C14—H14b	0.97
C4—C9	1.445 (3)	C15—H15a	0.97
C5—C6	1.444 (3)	C15—H15b	0.97
C6—C7	1.572 (3)	C16—H16a	0.97
C7—C8	1.497 (3)	C16—H16b	0.97
C8—C9	1.414 (3)	C18—H18a	0.96
C8—C13	1.421 (3)	C18—H18b	0.96
C9—C10	1.380 (4)	C18—H18c	0.96
C10—C11	1.372 (4)	C20—H20a	0.96
C11—C12	1.392 (4)	C20—H20b	0.96
C12—C13	1.407 (4)	C20—H20c	0.96
C12—C17	1.535 (3)	C1'—H21	0.93
C13—C14	1.513 (3)	C3'—H23a	0.96
C14—C15	1.521 (4)	C3'—H23b	0.96
C15—C16	1.505 (5)	C3'—H23c	0.96
C16—C17	1.532 (4)	C10'—H30	0.93
C17—C19	1.521 (4)	C11'—H31	0.93
C17—C18	1.541 (4)	C14'—H34a	0.97
C1'—C2'	1.335 (4)	C14'—H34b	0.97
C2'—C5'	1.442 (4)	C15'—H35a	0.97
C2'—C3'	1.496 (4)	C15'—H35b	0.97
C4'—C5'	1.361 (4)	C16'—H36a	0.97
C4'—C9'	1.444 (3)	C16'—H36b	0.97
C5'—C6'	1.442 (3)	C18'—H38a	0.96
C6'—C7'	1.570 (3)	C18'—H38b	0.96
C7'—C8'	1.493 (3)	C18'—H38c	0.96
C8'—C9'	1.417 (3)	C20'—H40a	0.96
C8'—C13'	1.423 (3)	C20'—H40b	0.96
C9'—C10'	1.376 (3)	C20'—H40c	0.96
C4—O1—C1	105.7 (2)	C16'—C17'—C12'	111.8 (2)
C19—O5—C20	117.7 (3)	C19'—C17'—C12'	105.4 (2)
C4'—O1'—C1'	105.7 (2)	O4'—C19'—O5'	123.0 (3)
C19'—O5'—C20'	116.1 (3)	O4'—C19'—C17'	124.6 (3)
C2—C1—O1	112.2 (2)	O5'—C19'—C17'	112.4 (3)
C1—C2—C5	104.6 (2)	C2—C1—H1	123.9
C1—C2—C3	128.2 (2)	O1—C1—H1	123.9
C5—C2—C3	127.2 (3)	C2—C3—H3a	109.5
O1—C4—C5	110.4 (2)	C2—C3—H3b	109.5
O1—C4—C9	121.2 (2)	H3a—C3—H3b	109.5
C5—C4—C9	128.3 (2)	C2—C3—H3c	109.5
C4—C5—C6	119.3 (2)	H3a—C3—H3c	109.5
C4—C5—C2	107.1 (2)	H3b—C3—H3c	109.5
C6—C5—C2	133.6 (2)	C11—C10—H10	120.4
O2—C6—C5	126.0 (2)	C9—C10—H10	120.4
O2—C6—C7	118.2 (2)	C10—C11—H11	118.9
C5—C6—C7	115.8 (2)	C12—C11—H11	118.9
O3—C7—C8	124.5 (2)	C13—C14—H14a	108.5
O3—C7—C6	115.4 (2)	C15—C14—H14a	108.5
C8—C7—C6	120.1 (2)	C13—C14—H14b	108.5
C9—C8—C13	119.3 (2)	C15—C14—H14b	108.5
C9—C8—C7	118.5 (2)	H14a—C14—H14b	107.5
C13—C8—C7	122.2 (2)	C16—C15—H15a	109.3
C10—C9—C8	120.8 (2)	C14—C15—H15a	109.3
C10—C9—C4	121.3 (2)	C16—C15—H15b	109.3
C8—C9—C4	117.8 (2)	C14—C15—H15b	109.3
C11—C10—C9	119.2 (2)	H15a—C15—H15b	108.0
C10—C11—C12	122.3 (2)	C15—C16—H16a	109.6
C11—C12—C13	119.4 (2)	C17—C16—H16a	109.6
C11—C12—C17	118.3 (2)	C15—C16—H16b	109.6
C13—C12—C17	122.2 (2)	C17—C16—H16b	109.6
C12—C13—C8	118.7 (2)	H16a—C16—H16b	108.1
C12—C13—C14	120.8 (2)	C17—C18—H18a	109.5
C8—C13—C14	120.5 (2)	C17—C18—H18b	109.5
C13—C14—C15	114.9 (2)	H18a—C18—H18b	109.5
C16—C15—C14	111.5 (2)	C17—C18—H18c	109.5
C15—C16—C17	110.5 (3)	H18a—C18—H18c	109.5
C19—C17—C16	110.1 (2)	H18b—C18—H18c	109.5
C19—C17—C12	109.3 (2)	O5—C20—H20a	109.5
C16—C17—C12	109.1 (2)	O5—C20—H20b	109.5
C19—C17—C18	108.6 (2)	H20a—C20—H20b	109.5
C16—C17—C18	108.4 (3)	O5—C20—H20c	109.5
C12—C17—C18	111.4 (2)	H20a—C20—H20c	109.5
O4—C19—O5	122.7 (3)	H20b—C20—H20c	109.5
O4—C19—C17	126.3 (2)	C2'—C1'—H21	123.9
O5—C19—C17	111.0 (2)	O1'—C1'—H21	123.9
C2'—C1'—O1'	112.2 (2)	C2'—C3'—H23a	109.5
C1'—C2'—C5'	104.6 (2)	C2'—C3'—H23b	109.5
C1'—C2'—C3'	128.4 (3)	H23a—C3'—H23b	109.5
C5'—C2'—C3'	127.0 (3)	C2'—C3'—H23c	109.5
O1'—C4'—C5'	110.2 (2)	H23a—C3'—H23c	109.5
O1'—C4'—C9'	121.4 (2)	H23b—C3'—H23c	109.5
C5'—C4'—C9'	128.4 (2)	C9'—C10'—H30	120.3
C4'—C5'—C2'	107.2 (2)	C11'—C10'—H30	120.3
C4'—C5'—C6'	119.0 (2)	C10'—C11'—H31	119.1
C2'—C5'—C6'	133.7 (2)	C12'—C11'—H31	119.1
O2'—C6'—C5'	125.6 (2)	C13'—C14'—H34a	109.1
O2'—C6'—C7'	118.3 (2)	C15'—C14'—H34a	109.1
C5'—C6'—C7'	116.1 (2)	C13'—C14'—H34b	109.1
O3'—C7'—C8'	124.3 (2)	C15'—C14'—H34b	109.1
O3'—C7'—C6'	115.6 (2)	H34a—C14'—H34b	107.8
C8'—C7'—C6'	120.0 (2)	C16'—C15'—H35a	109.5
C9'—C8'—C13'	119.3 (2)	C14'—C15'—H35a	109.5
C9'—C8'—C7'	118.5 (2)	C16'—C15'—H35b	109.5
C13'—C8'—C7'	122.2 (2)	C14'—C15'—H35b	109.5
C10'—C9'—C8'	121.0 (2)	H35a—C15'—H35b	108.1
C10'—C9'—C4'	121.3 (2)	C15'—C16'—H36a	109.4
C8'—C9'—C4'	117.7 (2)	C17'—C16'—H36a	109.4
C9'—C10'—C11'	119.3 (2)	C15'—C16'—H36b	109.4
C10'—C11'—C12'	121.9 (2)	C17'—C16'—H36b	109.4
C11'—C12'—C13'	120.0 (2)	H36a—C16'—H36b	108.0
C11'—C12'—C17'	116.9 (2)	C17'—C18'—H38a	109.5
C13'—C12'—C17'	123.1 (2)	C17'—C18'—H38b	109.5
C12'—C13'—C8'	118.5 (2)	H38a—C18'—H38b	109.5
C12'—C13'—C14'	120.0 (2)	C17'—C18'—H38c	109.5
C8'—C13'—C14'	121.4 (2)	H38a—C18'—H38c	109.5
C13'—C14'—C15'	112.5 (2)	H38b—C18'—H38c	109.5
C16'—C15'—C14'	110.6 (3)	O5'—C20'—H40a	109.5
C15'—C16'—C17'	111.0 (2)	O5'—C20'—H40b	109.5
C18'—C17'—C16'	110.3 (3)	H40a—C20'—H40b	109.5
C18'—C17'—C19'	112.4 (3)	O5'—C20'—H40c	109.5
C16'—C17'—C19'	107.3 (3)	H40a—C20'—H40c	109.5
C18'—C17'—C12'	109.5 (2)	H40b—C20'—H40c	109.5
C4—O1—C1—C2	0.0 (3)	C4'—O1'—C1'—C2'	0.3 (4)
O1—C1—C2—C5	0.2 (3)	O1'—C1'—C2'—C5'	−0.1 (4)
O1—C1—C2—C3	178.0 (3)	O1'—C1'—C2'—C3'	178.9 (3)
C1—O1—C4—C5	−0.3 (3)	C1'—O1'—C4'—C5'	−0.4 (3)
C1—O1—C4—C9	177.2 (2)	C1'—O1'—C4'—C9'	178.2 (3)
O1—C4—C5—C6	179.7 (2)	O1'—C4'—C5'—C2'	0.3 (3)
C9—C4—C5—C6	2.4 (4)	C9'—C4'—C5'—C2'	−178.1 (3)
O1—C4—C5—C2	0.4 (3)	O1'—C4'—C5'—C6'	−179.6 (2)
C9—C4—C5—C2	−176.9 (3)	C9'—C4'—C5'—C6'	1.9 (4)
C1—C2—C5—C4	−0.4 (3)	C1'—C2'—C5'—C4'	−0.2 (3)
C3—C2—C5—C4	−178.2 (3)	C3'—C2'—C5'—C4'	−179.1 (3)
C1—C2—C5—C6	−179.5 (3)	C1'—C2'—C5'—C6'	179.7 (3)
C3—C2—C5—C6	2.7 (6)	C3'—C2'—C5'—C6'	0.8 (6)
C4—C5—C6—O2	178.7 (3)	C4'—C5'—C6'—O2'	177.7 (3)
C2—C5—C6—O2	−2.3 (5)	C2'—C5'—C6'—O2'	−2.2 (5)
C4—C5—C6—C7	−0.9 (4)	C4'—C5'—C6'—C7'	−0.6 (4)
C2—C5—C6—C7	178.1 (3)	C2'—C5'—C6'—C7'	179.5 (3)
O2—C6—C7—O3	−1.8 (4)	O2'—C6'—C7'—O3'	−3.1 (4)
C5—C6—C7—O3	177.8 (3)	C5'—C6'—C7'—O3'	175.3 (3)
O2—C6—C7—C8	177.9 (3)	O2'—C6'—C7'—C8'	178.4 (3)
C5—C6—C7—C8	−2.5 (3)	C5'—C6'—C7'—C8'	−3.2 (4)
O3—C7—C8—C9	−175.7 (3)	O3'—C7'—C8'—C9'	−172.6 (3)
C6—C7—C8—C9	4.6 (3)	C6'—C7'—C8'—C9'	5.8 (4)
O3—C7—C8—C13	4.6 (4)	O3'—C7'—C8'—C13'	6.0 (4)
C6—C7—C8—C13	−175.1 (2)	C6'—C7'—C8'—C13'	−175.7 (2)
C13—C8—C9—C10	−3.1 (4)	C13'—C8'—C9'—C10'	−2.4 (4)
C7—C8—C9—C10	177.1 (3)	C7'—C8'—C9'—C10'	176.2 (3)
C13—C8—C9—C4	176.4 (2)	C13'—C8'—C9'—C4'	176.9 (2)
C7—C8—C9—C4	−3.3 (3)	C7'—C8'—C9'—C4'	−4.5 (4)
O1—C4—C9—C10	2.3 (4)	O1'—C4'—C9'—C10'	1.7 (4)
C5—C4—C9—C10	179.4 (3)	C5'—C4'—C9'—C10'	180.0 (3)
O1—C4—C9—C8	−177.2 (2)	O1'—C4'—C9'—C8'	−177.6 (3)
C5—C4—C9—C8	−0.2 (4)	C5'—C4'—C9'—C8'	0.7 (4)
C8—C9—C10—C11	4.7 (4)	C8'—C9'—C10'—C11'	1.0 (4)
C4—C9—C10—C11	−174.9 (3)	C4'—C9'—C10'—C11'	−178.2 (3)
C9—C10—C11—C12	−0.9 (4)	C9'—C10'—C11'—C12'	0.6 (5)
C10—C11—C12—C13	−4.5 (4)	C10'—C11'—C12'—C13'	−0.8 (4)
C10—C11—C12—C17	174.1 (3)	C10'—C11'—C12'—C17'	178.7 (3)
C11—C12—C13—C8	5.8 (4)	C11'—C12'—C13'—C8'	−0.6 (4)
C17—C12—C13—C8	−172.7 (2)	C17'—C12'—C13'—C8'	180.0 (2)
C11—C12—C13—C14	−175.4 (3)	C11'—C12'—C13'—C14'	178.0 (3)
C17—C12—C13—C14	6.1 (4)	C17'—C12'—C13'—C14'	−1.4 (4)
C9—C8—C13—C12	−2.2 (4)	C9'—C8'—C13'—C12'	2.1 (4)
C7—C8—C13—C12	177.6 (2)	C7'—C8'—C13'—C12'	−176.4 (2)
C9—C8—C13—C14	179.1 (2)	C9'—C8'—C13'—C14'	−176.5 (2)
C7—C8—C13—C14	−1.2 (4)	C7'—C8'—C13'—C14'	5.0 (4)
C12—C13—C14—C15	1.2 (4)	C12'—C13'—C14'—C15'	−19.8 (4)
C8—C13—C14—C15	179.9 (3)	C8'—C13'—C14'—C15'	158.7 (3)
C13—C14—C15—C16	−35.6 (4)	C13'—C14'—C15'—C16'	52.5 (4)
C14—C15—C16—C17	63.9 (3)	C14'—C15'—C16'—C17'	−64.7 (4)
C15—C16—C17—C19	65.1 (3)	C15'—C16'—C17'—C18'	−80.5 (3)
C15—C16—C17—C12	−54.7 (3)	C15'—C16'—C17'—C19'	156.8 (3)
C15—C16—C17—C18	−176.2 (2)	C15'—C16'—C17'—C12'	41.7 (4)
C11—C12—C17—C19	81.7 (3)	C11'—C12'—C17'—C18'	−66.5 (3)
C13—C12—C17—C19	−99.8 (3)	C13'—C12'—C17'—C18'	112.9 (3)
C11—C12—C17—C16	−157.9 (3)	C11'—C12'—C17'—C16'	170.9 (3)
C13—C12—C17—C16	20.6 (4)	C13'—C12'—C17'—C16'	−9.7 (4)
C11—C12—C17—C18	−38.3 (3)	C11'—C12'—C17'—C19'	54.6 (3)
C13—C12—C17—C18	140.2 (3)	C13'—C12'—C17'—C19'	−126.0 (3)
C20—O5—C19—O4	2.7 (5)	C20'—O5'—C19'—O4'	−4.2 (5)
C20—O5—C19—C17	−177.6 (3)	C20'—O5'—C19'—C17'	174.5 (3)
C16—C17—C19—O4	−117.1 (4)	C18'—C17'—C19'—O4'	−164.4 (3)
C12—C17—C19—O4	2.7 (4)	C16'—C17'—C19'—O4'	−43.0 (4)
C18—C17—C19—O4	124.4 (4)	C12'—C17'—C19'—O4'	76.3 (4)
C16—C17—C19—O5	63.2 (3)	C18'—C17'—C19'—O5'	16.9 (3)
C12—C17—C19—O5	−177.1 (2)	C16'—C17'—C19'—O5'	138.4 (3)
C18—C17—C19—O5	−55.4 (3)	C12'—C17'—C19'—O5'	−102.3 (3)