Conformations of imperatorin

The crystal structure of a pure sample of 9-(3-methyl­but-2-enyl­oxy)-7H-furo­[3,2-g]­chromen-7-one or imperatorin, C₁₆H₁₄O₄, is composed of two independent mol­ecules with different conformations of the 3-methyl­butyl group. The structure of an impure sample of imperatorin has already been reported [Cox, Jaspars, Kumarasamy, Nahar, Sarker & Shoeb (2003). Acta Cryst. C59, o520-o522.]

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.048
• wR factor = 0.142
• Data-to-parameter ratio = 21.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       5.05 Ratio

Author Response: Terminal methyl C-atoms show large thermal displacement parameters indicating a small degree of disorder.

Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.00 Ratio

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.47 Ratio

Author Response: Terminal methyl C-atoms show large thermal displacement parameters indicating a small degree of disorder.

PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.29 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for        C1'
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        C3'
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for       C13'
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C16 H14 O4

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 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
   5 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: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

9-(3-methylbut-2-enyloxy)-7H-furo[3,2-g]chromen-7-one

Crystal data

C16H14O4	Z = 4
Mr = 270.27	F(000) = 568
Triclinic, P1	Dx = 1.307 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.041 (6) Å	Cell parameters from 14651 reflections
b = 11.729 (6) Å	θ = 2.9–30.0°
c = 11.800 (7) Å	µ = 0.09 mm^−1
α = 64.72 (4)°	T = 173 K
β = 89.47 (3)°	Block, colorless
γ = 84.17 (2)°	0.35 × 0.32 × 0.18 mm
V = 1373.6 (13) Å^3

Data collection

Nonius KappaCCD diffractometer	6297 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 30.0°, θmin = 2.9°
ω and φ scans	h = −15→14
14651 measured reflections	k = −16→16
7853 independent reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.075P)^2 + 0.4P] where P = (Fo^2 + 2Fc^2)/3
7853 reflections	(Δ/σ)max = 0.001
361 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.14511 (7)	0.18938 (8)	0.47373 (8)	0.02866 (19)
C2	0.23441 (11)	0.15566 (12)	0.40654 (12)	0.0322 (3)
H2	0.3191	0.1577	0.4178	0.039*
C3	0.18727 (11)	0.11993 (12)	0.32403 (12)	0.0309 (3)
H3	0.2311	0.0935	0.2682	0.037*
C4a	0.05685 (10)	0.12952 (11)	0.33648 (10)	0.0250 (2)
C4	−0.04210 (11)	0.10506 (11)	0.28198 (10)	0.0266 (2)
H4	−0.0312	0.0773	0.2174	0.032*
C5a	−0.15831 (10)	0.12222 (10)	0.32431 (10)	0.0231 (2)
C5	−0.26659 (11)	0.09624 (12)	0.27659 (11)	0.0282 (2)
H5	−0.2605	0.0692	0.2113	0.034*
C6	−0.37588 (11)	0.10949 (12)	0.32269 (11)	0.0297 (2)
H6	−0.4452	0.0882	0.2919	0.036*
C7	−0.39027 (10)	0.15539 (12)	0.41815 (11)	0.0274 (2)
O71	−0.48490 (8)	0.17358 (11)	0.46376 (10)	0.0420 (2)
O8	−0.28708 (7)	0.18429 (8)	0.46069 (7)	0.02450 (17)
C8a	−0.17352 (9)	0.16544 (10)	0.41837 (9)	0.0211 (2)
C9	−0.07616 (10)	0.19276 (10)	0.47340 (9)	0.0216 (2)
C9a	0.03736 (10)	0.17244 (10)	0.43010 (10)	0.0233 (2)
O10	−0.09238 (7)	0.23195 (8)	0.56679 (7)	0.02543 (17)
C1'	−0.1078 (2)	0.36886 (14)	0.51872 (15)	0.0549 (5)
H1'1	−0.1785	0.4044	0.4585	0.066*
H1'2	−0.0343	0.4043	0.4743	0.066*
C2'	−0.12754 (15)	0.40332 (13)	0.62473 (13)	0.0399 (3)
H2'	−0.0615	0.3816	0.6838	0.048*
C3'	−0.22839 (17)	0.46143 (14)	0.64490 (16)	0.0496 (4)
C4'	−0.2358 (3)	0.48941 (19)	0.7577 (2)	0.0823 (8)
H41	−0.3165	0.5325	0.7582	0.123*	0.50
H42	−0.1732	0.5441	0.7545	0.123*	0.50
H43	−0.2226	0.4098	0.8340	0.123*	0.50
H44	−0.1583	0.4585	0.8063	0.123*	0.50
H45	−0.3016	0.4469	0.8100	0.123*	0.50
H46	−0.2523	0.5812	0.7305	0.123*	0.50
C5'	−0.3440 (3)	0.4998 (3)	0.5669 (3)	0.1064 (10)
H51	−0.4047	0.5412	0.6021	0.160*	0.50
H52	−0.3747	0.4245	0.5664	0.160*	0.50
H53	−0.3284	0.5590	0.4809	0.160*	0.50
H54	−0.3338	0.4752	0.4974	0.160*	0.50
H55	−0.3639	0.5920	0.5332	0.160*	0.50
H56	−0.4101	0.4575	0.6187	0.160*	0.50
O11	0.16999 (7)	0.15992 (9)	−0.01158 (8)	0.0318 (2)
C12	0.08800 (12)	0.16324 (14)	−0.10183 (14)	0.0389 (3)
H12	0.0025	0.1633	−0.0918	0.047*
C13	0.14312 (12)	0.16639 (14)	−0.20465 (14)	0.0378 (3)
H13	0.1050	0.1694	−0.2779	0.045*
C14a	0.27216 (11)	0.16423 (12)	−0.18230 (11)	0.0287 (2)
C14	0.37703 (12)	0.16291 (12)	−0.24755 (11)	0.0293 (2)
H14	0.3726	0.1644	−0.3285	0.035*
C15a	0.48926 (11)	0.15931 (11)	−0.19195 (10)	0.0251 (2)
C15	0.60371 (12)	0.15286 (12)	−0.25001 (11)	0.0306 (3)
H15	0.6041	0.1516	−0.3300	0.037*
C16	0.70946 (12)	0.14864 (12)	−0.19298 (12)	0.0320 (3)
H16	0.7836	0.1424	−0.2325	0.038*
C17	0.71337 (11)	0.15343 (12)	−0.07275 (11)	0.0294 (2)
O171	0.80358 (8)	0.15319 (11)	−0.01528 (9)	0.0420 (2)
O18	0.60337 (7)	0.16047 (8)	−0.01767 (7)	0.02636 (18)
C18a	0.49426 (10)	0.16017 (10)	−0.07300 (10)	0.0222 (2)
C19	0.39048 (10)	0.16263 (10)	−0.00562 (10)	0.0222 (2)
C19a	0.28173 (10)	0.16137 (11)	−0.06231 (11)	0.0252 (2)
O110	0.39638 (7)	0.16616 (8)	0.10895 (7)	0.02527 (17)
C11'	0.39656 (12)	0.29626 (12)	0.09559 (12)	0.0321 (3)
H111	0.4662	0.3346	0.0453	0.039*
H112	0.4069	0.2948	0.1795	0.039*
C12'	0.28111 (13)	0.37486 (12)	0.03354 (12)	0.0352 (3)
H12'	0.2112	0.3597	0.0833	0.042*
C13'	0.26463 (16)	0.46422 (14)	−0.08409 (14)	0.0463 (4)
C14'	0.3640 (2)	0.5066 (2)	−0.17609 (19)	0.0768 (7)
H141	0.3293	0.5730	−0.2560	0.115*	0.50
H142	0.4020	0.4343	−0.1895	0.115*	0.50
H143	0.4255	0.5401	−0.1429	0.115*	0.50
H144	0.4419	0.4587	−0.1362	0.115*	0.50
H145	0.3692	0.5973	−0.2027	0.115*	0.50
H146	0.3457	0.4915	−0.2493	0.115*	0.50
C15'	0.1379 (2)	0.5264 (2)	−0.1352 (2)	0.0760 (6)
H151	0.1422	0.5893	−0.2223	0.114*	0.50
H152	0.1029	0.5685	−0.0845	0.114*	0.50
H153	0.0865	0.4619	−0.1321	0.114*	0.50
H154	0.0789	0.4905	−0.0703	0.114*	0.50
H155	0.1181	0.5113	−0.2081	0.114*	0.50
H156	0.1346	0.6179	−0.1605	0.114*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0187 (4)	0.0391 (5)	0.0294 (4)	−0.0072 (3)	0.0017 (3)	−0.0150 (4)
C2	0.0203 (5)	0.0366 (6)	0.0338 (6)	−0.0043 (4)	0.0064 (4)	−0.0095 (5)
C3	0.0245 (6)	0.0333 (6)	0.0316 (6)	−0.0027 (4)	0.0094 (4)	−0.0110 (5)
C4a	0.0237 (5)	0.0275 (5)	0.0225 (5)	−0.0030 (4)	0.0060 (4)	−0.0095 (4)
C4	0.0304 (6)	0.0302 (5)	0.0222 (5)	−0.0035 (4)	0.0050 (4)	−0.0142 (4)
C5a	0.0247 (5)	0.0271 (5)	0.0193 (5)	−0.0031 (4)	0.0000 (4)	−0.0115 (4)
C5	0.0317 (6)	0.0341 (6)	0.0235 (5)	−0.0038 (5)	−0.0036 (4)	−0.0166 (5)
C6	0.0249 (6)	0.0385 (6)	0.0295 (6)	−0.0039 (5)	−0.0065 (4)	−0.0179 (5)
C7	0.0202 (5)	0.0361 (6)	0.0270 (5)	−0.0029 (4)	−0.0019 (4)	−0.0145 (5)
O71	0.0205 (4)	0.0692 (7)	0.0475 (6)	−0.0056 (4)	0.0026 (4)	−0.0356 (5)
O8	0.0182 (4)	0.0353 (4)	0.0248 (4)	−0.0033 (3)	0.0013 (3)	−0.0173 (3)
C8a	0.0190 (5)	0.0262 (5)	0.0188 (4)	−0.0025 (4)	0.0016 (3)	−0.0104 (4)
C9	0.0222 (5)	0.0266 (5)	0.0183 (4)	−0.0042 (4)	0.0012 (4)	−0.0114 (4)
C9a	0.0201 (5)	0.0274 (5)	0.0219 (5)	−0.0055 (4)	0.0012 (4)	−0.0094 (4)
O10	0.0279 (4)	0.0328 (4)	0.0216 (4)	−0.0058 (3)	0.0023 (3)	−0.0168 (3)
C1'	0.0998 (14)	0.0334 (7)	0.0375 (7)	−0.0115 (8)	0.0231 (8)	−0.0205 (6)
C2'	0.0537 (8)	0.0373 (7)	0.0359 (7)	−0.0087 (6)	0.0062 (6)	−0.0218 (6)
C3'	0.0690 (11)	0.0346 (7)	0.0468 (8)	−0.0022 (7)	0.0103 (7)	−0.0198 (6)
C4'	0.142 (2)	0.0491 (10)	0.0635 (12)	−0.0011 (12)	0.0380 (13)	−0.0344 (10)
C5'	0.0879 (19)	0.094 (2)	0.116 (2)	0.0330 (15)	−0.0231 (17)	−0.0328 (17)
O11	0.0193 (4)	0.0441 (5)	0.0356 (5)	−0.0027 (3)	0.0019 (3)	−0.0208 (4)
C12	0.0237 (6)	0.0500 (8)	0.0472 (8)	−0.0021 (5)	−0.0066 (5)	−0.0250 (6)
C13	0.0292 (6)	0.0481 (8)	0.0419 (7)	−0.0012 (5)	−0.0093 (5)	−0.0253 (6)
C14a	0.0284 (6)	0.0335 (6)	0.0284 (5)	−0.0022 (4)	−0.0042 (4)	−0.0173 (5)
C14	0.0352 (6)	0.0343 (6)	0.0224 (5)	−0.0037 (5)	−0.0008 (4)	−0.0160 (5)
C15a	0.0291 (6)	0.0279 (5)	0.0211 (5)	−0.0038 (4)	0.0042 (4)	−0.0131 (4)
C15	0.0370 (6)	0.0355 (6)	0.0232 (5)	−0.0068 (5)	0.0105 (5)	−0.0157 (5)
C16	0.0300 (6)	0.0381 (6)	0.0298 (6)	−0.0073 (5)	0.0124 (5)	−0.0158 (5)
C17	0.0235 (5)	0.0350 (6)	0.0289 (5)	−0.0048 (4)	0.0071 (4)	−0.0129 (5)
O171	0.0230 (4)	0.0655 (7)	0.0394 (5)	−0.0077 (4)	0.0035 (4)	−0.0237 (5)
O18	0.0198 (4)	0.0385 (4)	0.0245 (4)	−0.0038 (3)	0.0029 (3)	−0.0168 (3)
C18a	0.0213 (5)	0.0262 (5)	0.0212 (5)	−0.0029 (4)	0.0011 (4)	−0.0120 (4)
C19	0.0231 (5)	0.0261 (5)	0.0189 (5)	−0.0015 (4)	0.0020 (4)	−0.0115 (4)
C19a	0.0208 (5)	0.0306 (5)	0.0265 (5)	−0.0017 (4)	0.0017 (4)	−0.0147 (4)
O110	0.0269 (4)	0.0329 (4)	0.0185 (3)	−0.0006 (3)	0.0017 (3)	−0.0139 (3)
C11'	0.0387 (7)	0.0366 (6)	0.0283 (6)	−0.0043 (5)	0.0020 (5)	−0.0208 (5)
C12'	0.0450 (7)	0.0325 (6)	0.0299 (6)	0.0016 (5)	0.0055 (5)	−0.0165 (5)
C13'	0.0594 (10)	0.0348 (7)	0.0380 (7)	−0.0008 (6)	0.0027 (6)	−0.0101 (6)
C14'	0.0831 (15)	0.0705 (13)	0.0474 (10)	−0.0201 (11)	0.0138 (10)	0.0049 (9)
C15'	0.0764 (14)	0.0579 (11)	0.0584 (11)	0.0186 (10)	−0.0045 (10)	0.0031 (9)

Geometric parameters (Å, º)

O1—C9a	1.3662 (14)	O11—C19a	1.3648 (15)
O1—C2	1.3897 (16)	O11—C12	1.3894 (17)
C2—C3	1.340 (2)	C12—C13	1.340 (2)
C2—H2	0.9500	C12—H12	0.9500
C3—C4a	1.4440 (18)	C13—C14a	1.4471 (19)
C3—H3	0.9500	C13—H13	0.9500
C4a—C4	1.3870 (17)	C14a—C14	1.3870 (18)
C4a—C9a	1.4033 (17)	C14a—C19a	1.4065 (18)
C4—C5a	1.3992 (17)	C14—C15a	1.3958 (18)
C4—H4	0.9500	C14—H14	0.9500
C5a—C8a	1.4059 (16)	C15a—C18a	1.4096 (17)
C5a—C5	1.4396 (16)	C15a—C15	1.4425 (17)
C5—C6	1.3409 (18)	C15—C16	1.3390 (19)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.4426 (18)	C16—C17	1.4448 (19)
C6—H6	0.9500	C16—H16	0.9500
C7—O71	1.2121 (16)	C17—O171	1.2093 (17)
C7—O8	1.3782 (14)	C17—O18	1.3838 (15)
O8—C8a	1.3772 (14)	O18—C18a	1.3766 (15)
C8a—C9	1.3931 (15)	C18a—C19	1.3934 (16)
C9—O10	1.3675 (14)	C19—O110	1.3725 (15)
C9—C9a	1.3857 (16)	C19—C19a	1.3843 (17)
O10—C1'	1.4483 (19)	O110—C11'	1.4657 (17)
C1'—C2'	1.478 (2)	C11'—C12'	1.488 (2)
C1'—H1'1	0.9900	C11'—H111	0.9900
C1'—H1'2	0.9900	C11'—H112	0.9900
C2'—C3'	1.319 (2)	C12'—C13'	1.335 (2)
C2'—H2'	0.9500	C12'—H12'	0.9500
C3'—C5'	1.493 (3)	C13'—C14'	1.503 (3)
C3'—C4'	1.501 (3)	C13'—C15'	1.512 (3)
C4'—H41	0.9800	C14'—H141	0.9800
C4'—H42	0.9800	C14'—H142	0.9800
C4'—H43	0.9800	C14'—H143	0.9800
C4'—H44	0.9800	C14'—H144	0.9800
C4'—H45	0.9800	C14'—H145	0.9800
C4'—H46	0.9800	C14'—H146	0.9800
C5'—H51	0.9800	C15'—H151	0.9800
C5'—H52	0.9800	C15'—H152	0.9800
C5'—H53	0.9800	C15'—H153	0.9800
C5'—H54	0.9800	C15'—H154	0.9800
C5'—H55	0.9800	C15'—H155	0.9800
C5'—H56	0.9800	C15'—H156	0.9800
C9a—O1—C2	105.27 (10)	C19a—O11—C12	105.30 (10)
C3—C2—O1	112.23 (11)	C13—C12—O11	112.37 (12)
C3—C2—H2	123.9	C13—C12—H12	123.8
O1—C2—H2	123.9	O11—C12—H12	123.8
C2—C3—C4a	106.63 (11)	C12—C13—C14a	106.55 (12)
C2—C3—H3	126.7	C12—C13—H13	126.7
C4a—C3—H3	126.7	C14a—C13—H13	126.7
C4—C4a—C9a	119.31 (10)	C14—C14a—C19a	119.31 (11)
C4—C4a—C3	135.74 (11)	C14—C14a—C13	135.88 (12)
C9a—C4a—C3	104.94 (11)	C19a—C14a—C13	104.80 (11)
C4a—C4—C5a	118.43 (11)	C14a—C14—C15a	118.75 (11)
C4a—C4—H4	120.8	C14a—C14—H14	120.6
C5a—C4—H4	120.8	C15a—C14—H14	120.6
C4—C5a—C8a	120.29 (10)	C14—C15a—C18a	120.00 (11)
C4—C5a—C5	122.90 (11)	C14—C15a—C15	122.97 (11)
C8a—C5a—C5	116.81 (10)	C18a—C15a—C15	117.03 (11)
C6—C5—C5a	121.18 (11)	C16—C15—C15a	121.04 (11)
C6—C5—H5	119.4	C16—C15—H15	119.5
C5a—C5—H5	119.4	C15a—C15—H15	119.5
C5—C6—C7	121.34 (11)	C15—C16—C17	121.49 (11)
C5—C6—H6	119.3	C15—C16—H16	119.3
C7—C6—H6	119.3	C17—C16—H16	119.3
O71—C7—O8	116.09 (11)	O171—C17—O18	116.21 (11)
O71—C7—C6	126.55 (11)	O171—C17—C16	126.47 (12)
O8—C7—C6	117.35 (10)	O18—C17—C16	117.32 (11)
C8a—O8—C7	121.84 (9)	C18a—O18—C17	121.84 (10)
O8—C8a—C9	116.04 (10)	O18—C18a—C19	116.20 (10)
O8—C8a—C5a	121.37 (10)	O18—C18a—C15a	121.19 (10)
C9—C8a—C5a	122.59 (10)	C19—C18a—C15a	122.60 (10)
O10—C9—C9a	123.04 (10)	O110—C19—C19a	122.61 (10)
O10—C9—C8a	121.76 (10)	O110—C19—C18a	122.01 (10)
C9a—C9—C8a	115.15 (10)	C19a—C19—C18a	115.38 (10)
O1—C9a—C9	124.85 (10)	O11—C19a—C19	125.13 (11)
O1—C9a—C4a	110.93 (10)	O11—C19a—C14a	110.98 (10)
C9—C9a—C4a	124.22 (10)	C19—C19a—C14a	123.88 (11)
C9—O10—C1'	112.25 (10)	C19—O110—C11'	111.54 (9)
O10—C1'—C2'	108.89 (12)	O110—C11'—C12'	111.10 (11)
O10—C1'—H1'1	109.9	O110—C11'—H111	109.4
C2'—C1'—H1'1	109.9	C12'—C11'—H111	109.4
O10—C1'—H1'2	109.9	O110—C11'—H112	109.4
C2'—C1'—H1'2	109.9	C12'—C11'—H112	109.4
H1'1—C1'—H1'2	108.3	H111—C11'—H112	108.0
C3'—C2'—C1'	126.04 (17)	C13'—C12'—C11'	127.37 (14)
C3'—C2'—H2'	117.0	C13'—C12'—H12'	116.3
C1'—C2'—H2'	117.0	C11'—C12'—H12'	116.3
C2'—C3'—C5'	125.85 (19)	C12'—C13'—C14'	124.74 (17)
C2'—C3'—C4'	120.20 (19)	C12'—C13'—C15'	120.07 (16)
C5'—C3'—C4'	113.9 (2)	C14'—C13'—C15'	115.13 (16)
C3'—C4'—H41	109.5	C13'—C14'—H141	109.5
C3'—C4'—H42	109.5	C13'—C14'—H142	109.5
H41—C4'—H42	109.5	H141—C14'—H142	109.5
C3'—C4'—H43	109.5	C13'—C14'—H143	109.5
H41—C4'—H43	109.5	H141—C14'—H143	109.5
H42—C4'—H43	109.5	H142—C14'—H143	109.5
C3'—C4'—H44	109.5	C13'—C14'—H144	109.5
H41—C4'—H44	141.1	H141—C14'—H144	141.1
H42—C4'—H44	56.3	H142—C14'—H144	56.3
H43—C4'—H44	56.3	H143—C14'—H144	56.3
C3'—C4'—H45	109.5	C13'—C14'—H145	109.5
H41—C4'—H45	56.3	H141—C14'—H145	56.3
H42—C4'—H45	141.1	H142—C14'—H145	141.1
H43—C4'—H45	56.3	H143—C14'—H145	56.3
H44—C4'—H45	109.5	H144—C14'—H145	109.5
C3'—C4'—H46	109.5	C13'—C14'—H146	109.5
H41—C4'—H46	56.3	H141—C14'—H146	56.3
H42—C4'—H46	56.3	H142—C14'—H146	56.3
H43—C4'—H46	141.1	H143—C14'—H146	141.1
H44—C4'—H46	109.5	H144—C14'—H146	109.5
H45—C4'—H46	109.5	H145—C14'—H146	109.5
C3'—C5'—H51	109.5	C13'—C15'—H151	109.5
C3'—C5'—H52	109.5	C13'—C15'—H152	109.5
H51—C5'—H52	109.5	H151—C15'—H152	109.5
C3'—C5'—H53	109.5	C13'—C15'—H153	109.5
H51—C5'—H53	109.5	H151—C15'—H153	109.5
H52—C5'—H53	109.5	H152—C15'—H153	109.5
C3'—C5'—H54	109.5	C13'—C15'—H154	109.5
H51—C5'—H54	141.1	H151—C15'—H154	141.1
H52—C5'—H54	56.3	H152—C15'—H154	56.3
H53—C5'—H54	56.3	H153—C15'—H154	56.3
C3'—C5'—H55	109.5	C13'—C15'—H155	109.5
H51—C5'—H55	56.3	H151—C15'—H155	56.3
H52—C5'—H55	141.1	H152—C15'—H155	141.1
H53—C5'—H55	56.3	H153—C15'—H155	56.3
H54—C5'—H55	109.5	H154—C15'—H155	109.5
C3'—C5'—H56	109.5	C13'—C15'—H156	109.5
H51—C5'—H56	56.3	H151—C15'—H156	56.3
H52—C5'—H56	56.3	H152—C15'—H156	56.3
H53—C5'—H56	141.1	H153—C15'—H156	141.1
H54—C5'—H56	109.5	H154—C15'—H156	109.5
H55—C5'—H56	109.5	H155—C15'—H156	109.5
C9a—O1—C2—C3	0.38 (13)	C19a—O11—C12—C13	0.13 (16)
O1—C2—C3—C4a	−0.27 (14)	O11—C12—C13—C14a	0.38 (17)
C2—C3—C4a—C4	−178.54 (13)	C12—C13—C14a—C14	178.36 (15)
C2—C3—C4a—C9a	0.05 (13)	C12—C13—C14a—C19a	−0.71 (15)
C9a—C4a—C4—C5a	−1.08 (16)	C19a—C14a—C14—C15a	−0.27 (18)
C3—C4a—C4—C5a	177.37 (12)	C13—C14a—C14—C15a	−179.24 (14)
C4a—C4—C5a—C8a	1.11 (16)	C14a—C14—C15a—C18a	−1.52 (18)
C4a—C4—C5a—C5	−178.25 (10)	C14a—C14—C15a—C15	177.59 (11)
C4—C5a—C5—C6	177.57 (11)	C14—C15a—C15—C16	−179.51 (12)
C8a—C5a—C5—C6	−1.81 (17)	C18a—C15a—C15—C16	−0.37 (18)
C5a—C5—C6—C7	2.65 (19)	C15a—C15—C16—C17	−1.5 (2)
C5—C6—C7—O71	178.14 (13)	C15—C16—C17—O171	−178.17 (13)
C5—C6—C7—O8	−0.42 (18)	C15—C16—C17—O18	1.04 (18)
O71—C7—O8—C8a	178.60 (10)	O171—C17—O18—C18a	−179.31 (11)
C6—C7—O8—C8a	−2.69 (16)	C16—C17—O18—C18a	1.40 (16)
C7—O8—C8a—C9	−176.98 (10)	C17—O18—C18a—C19	177.56 (10)
C7—O8—C8a—C5a	3.56 (16)	C17—O18—C18a—C15a	−3.36 (16)
C4—C5a—C8a—O8	179.34 (10)	C14—C15a—C18a—O18	−178.06 (10)
C5—C5a—C8a—O8	−1.26 (15)	C15—C15a—C18a—O18	2.78 (16)
C4—C5a—C8a—C9	−0.08 (17)	C14—C15a—C18a—C19	0.97 (17)
C5—C5a—C8a—C9	179.32 (10)	C15—C15a—C18a—C19	−178.19 (10)
O8—C8a—C9—O10	2.07 (15)	O18—C18a—C19—O110	0.49 (16)
C5a—C8a—C9—O10	−178.48 (10)	C15a—C18a—C19—O110	−178.58 (10)
O8—C8a—C9—C9a	179.62 (9)	O18—C18a—C19—C19a	−179.56 (9)
C5a—C8a—C9—C9a	−0.93 (16)	C15a—C18a—C19—C19a	1.37 (16)
C2—O1—C9a—C9	178.70 (11)	C12—O11—C19a—C19	178.11 (12)
C2—O1—C9a—C4a	−0.33 (12)	C12—O11—C19a—C14a	−0.61 (14)
O10—C9—C9a—O1	−0.42 (17)	O110—C19—C19a—O11	−1.90 (18)
C8a—C9—C9a—O1	−177.93 (10)	C18a—C19—C19a—O11	178.15 (10)
O10—C9—C9a—C4a	178.49 (10)	O110—C19—C19a—C14a	176.66 (10)
C8a—C9—C9a—C4a	0.97 (16)	C18a—C19—C19a—C14a	−3.29 (17)
C4—C4a—C9a—O1	179.06 (10)	C14—C14a—C19a—O11	−178.43 (11)
C3—C4a—C9a—O1	0.18 (13)	C13—C14a—C19a—O11	0.82 (14)
C4—C4a—C9a—C9	0.02 (17)	C14—C14a—C19a—C19	2.84 (18)
C3—C4a—C9a—C9	−178.86 (11)	C13—C14a—C19a—C19	−177.91 (12)
C9a—C9—O10—C1'	89.32 (15)	C19a—C19—O110—C11'	−94.96 (13)
C8a—C9—O10—C1'	−93.33 (15)	C18a—C19—O110—C11'	84.99 (13)
C9—O10—C1'—C2'	178.71 (13)	C19—O110—C11'—C12'	63.13 (13)
O10—C1'—C2'—C3'	−114.01 (18)	O110—C11'—C12'—C13'	−105.50 (17)
C1'—C2'—C3'—C5'	2.3 (3)	C11'—C12'—C13'—C14'	−2.8 (3)
C1'—C2'—C3'—C4'	179.42 (16)	C11'—C12'—C13'—C15'	174.31 (17)