Qualitative and qu­anti­tative analysis of inter­molecular inter­actions in xanthenedione derivatives

The existence of inter­molecular inter­actions and the conformational geometry adopted by mol­ecules are related to biological activity. Xanthenedione mol­e­cules are promising and emerging anti­oxidants and acetyl­cholinesterase inhibitors. To examine the role of different functional groups involved in the inter­molecular inter­actions and conformational geometries adopted in xan­thene­diones, a series of three substituted xanthenediones have been crystallized [9-(3-hy­droxy­phen­yl)-3,3,6,6-tetra­methyl-3,4,5,6,7,9-hexa­hydro-1H-xanthene-1,8(2H)-dione, C₂₃H₂₆O₄, 9-(5-bromo-2-meth­oxy­phen­yl)-3,3,6,6-tetra­methyl-3,4,6,7-tetra­hydro-2H-xanthene-1,8(5H,9H)-dione, C₂₄H₂₇BrO₄, and 3,3,6,6-tetra­methyl-9-(pyridin-2-yl)-3,4,6,7-tetra­hydro-2H-xanthene-1,8(5H,9H)-dione, C₂₂H₂₅NO₃] and their inter­molecular inter­actions analyzed via Hirshfeld analysis. The results show that all the derivatives adopt the same structural conformation, where the central ring has a shallow boat conformation and the outer rings have a twisted boat conformation. The inter­molecular inter­actions in the mol­ecules are predominantly O—H...O, C—H...O and π–π inter­actions. The optimized structures of the derivatives from theoretical B3LYP/6-311G** calculations show a good correlation with the experimental structures. The lattice energy involved in the inter­molecular inter­actions has been explored using PIXELC.

Computing details

For all structures, data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: PLATON (Spek, 2009).

9-(3-Hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione (C1)

Crystal data

C23H26O4	F(000) = 784
Mr = 366.44	Dx = 1.226 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4016 reflections
a = 12.251 (6) Å	θ = 2.2–25.3°
b = 14.971 (8) Å	µ = 0.08 mm^−1
c = 10.868 (6) Å	T = 290 K
β = 95.289 (9)°	Prism, colourless
V = 1984.8 (18) Å^3	0.45 × 0.4 × 0.35 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2764 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→14
Tmin = 0.916, Tmax = 0.972	k = −17→18
14287 measured reflections	l = −13→13
3691 independent reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0548P)^2 + 0.3647P] where P = (Fo^2 + 2Fc^2)/3
3691 reflections	(Δ/σ)max = 0.001
249 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.12 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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 > 2sigma(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
O1	0.24218 (9)	−0.01076 (7)	−0.03813 (9)	0.0472 (4)
O2	0.27353 (11)	0.22940 (9)	0.24038 (13)	0.0661 (5)
O3	0.51822 (10)	−0.04768 (10)	0.28494 (12)	0.0679 (5)
O4	0.26677 (12)	0.01754 (13)	0.64481 (11)	0.0833 (6)
C1	0.47075 (14)	−0.07429 (12)	0.18810 (16)	0.0494 (6)
C2	0.51161 (16)	−0.15203 (14)	0.11931 (18)	0.0638 (7)
C3	0.42330 (17)	−0.20228 (13)	0.03960 (16)	0.0595 (7)
C4	0.36050 (16)	−0.13494 (12)	−0.04452 (15)	0.0541 (6)
C5	0.13847 (15)	0.11957 (12)	−0.08664 (15)	0.0495 (6)
C6	0.07690 (14)	0.19405 (12)	−0.02600 (15)	0.0501 (6)
C7	0.16144 (16)	0.24980 (12)	0.05197 (17)	0.0557 (6)
C8	0.23380 (14)	0.19717 (11)	0.14353 (16)	0.0468 (6)
C9	0.32854 (13)	0.04883 (11)	0.20318 (14)	0.0418 (5)
C10	0.37336 (13)	−0.02797 (11)	0.13432 (14)	0.0420 (5)
C11	0.32757 (13)	−0.05521 (11)	0.02472 (14)	0.0434 (5)
C12	0.21654 (13)	0.07274 (11)	0.00335 (14)	0.0412 (5)
C13	0.25886 (13)	0.10469 (10)	0.11185 (14)	0.0404 (5)
C14	0.3450 (2)	−0.24935 (15)	0.1196 (2)	0.0828 (9)
C15	0.4761 (3)	−0.27194 (18)	−0.0394 (2)	0.1037 (10)
C16	−0.00665 (16)	0.15491 (15)	0.05415 (18)	0.0647 (7)
C17	0.01719 (19)	0.25238 (15)	−0.1258 (2)	0.0745 (8)
C18	0.26309 (13)	0.01598 (10)	0.30783 (14)	0.0411 (5)
C19	0.29942 (13)	0.03028 (11)	0.42995 (15)	0.0454 (5)
C20	0.23767 (15)	0.00288 (13)	0.52342 (15)	0.0509 (6)
C21	0.13945 (16)	−0.03982 (13)	0.49475 (17)	0.0595 (7)
C22	0.10358 (17)	−0.05465 (15)	0.37370 (18)	0.0681 (8)
C23	0.16483 (15)	−0.02735 (13)	0.28047 (16)	0.0595 (7)
H2A	0.54777	−0.19340	0.17849	0.0766*
H2B	0.56608	−0.13080	0.06688	0.0766*
H4	0.33203	0.03047	0.65478	0.1249*
H4A	0.29549	−0.16329	−0.08469	0.0648*
H4B	0.40601	−0.11615	−0.10826	0.0648*
H5A	0.08603	0.07684	−0.12430	0.0594*
H5B	0.17815	0.14487	−0.15157	0.0594*
H7A	0.12329	0.29472	0.09600	0.0669*
H7B	0.20702	0.28072	−0.00276	0.0669*
H9	0.38997	0.08526	0.23885	0.0501*
H14A	0.31027	−0.20592	0.16808	0.1241*
H14B	0.38517	−0.29100	0.17353	0.1241*
H14C	0.29011	−0.28073	0.06762	0.1241*
H15A	0.52230	−0.24245	−0.09351	0.1552*
H15B	0.51933	−0.31248	0.01337	0.1552*
H15C	0.41988	−0.30456	−0.08767	0.1552*
H16A	−0.04445	0.20247	0.09159	0.0970*
H16B	0.03025	0.11829	0.11750	0.0970*
H16C	−0.05849	0.11928	0.00395	0.0970*
H17A	−0.02523	0.29676	−0.08776	0.1118*
H17B	−0.03056	0.21586	−0.17972	0.1118*
H17C	0.06978	0.28124	−0.17264	0.1118*
H19	0.36624	0.05869	0.44982	0.0545*
H21	0.09768	−0.05849	0.55721	0.0714*
H22	0.03703	−0.08350	0.35403	0.0817*
H23	0.13961	−0.03829	0.19851	0.0714*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0541 (7)	0.0458 (7)	0.0400 (6)	0.0091 (5)	−0.0053 (5)	−0.0062 (5)
O2	0.0662 (9)	0.0573 (8)	0.0722 (9)	−0.0049 (7)	−0.0074 (7)	−0.0218 (7)
O3	0.0523 (8)	0.0882 (10)	0.0599 (8)	0.0041 (7)	−0.0125 (6)	0.0005 (7)
O4	0.0705 (10)	0.1409 (15)	0.0380 (7)	−0.0248 (10)	0.0031 (6)	−0.0011 (8)
C1	0.0408 (9)	0.0618 (11)	0.0455 (9)	−0.0010 (9)	0.0036 (8)	0.0100 (8)
C2	0.0570 (12)	0.0796 (14)	0.0555 (11)	0.0256 (11)	0.0090 (9)	0.0094 (10)
C3	0.0738 (13)	0.0556 (11)	0.0496 (10)	0.0213 (10)	0.0080 (9)	0.0005 (9)
C4	0.0627 (12)	0.0564 (11)	0.0432 (9)	0.0127 (9)	0.0056 (8)	−0.0042 (8)
C5	0.0560 (10)	0.0510 (10)	0.0410 (9)	0.0074 (9)	0.0018 (8)	0.0023 (8)
C6	0.0517 (10)	0.0504 (10)	0.0477 (9)	0.0088 (8)	0.0015 (8)	−0.0007 (8)
C7	0.0625 (12)	0.0427 (9)	0.0627 (11)	0.0048 (9)	0.0095 (9)	−0.0010 (9)
C8	0.0427 (10)	0.0454 (10)	0.0526 (10)	−0.0094 (8)	0.0061 (8)	−0.0079 (8)
C9	0.0375 (9)	0.0461 (9)	0.0410 (8)	−0.0081 (7)	−0.0005 (7)	−0.0036 (7)
C10	0.0397 (9)	0.0464 (9)	0.0400 (8)	−0.0021 (7)	0.0044 (7)	0.0022 (7)
C11	0.0442 (9)	0.0465 (9)	0.0397 (8)	0.0053 (8)	0.0045 (7)	0.0037 (7)
C12	0.0446 (9)	0.0403 (9)	0.0392 (8)	0.0015 (7)	0.0061 (7)	0.0004 (7)
C13	0.0397 (9)	0.0413 (9)	0.0402 (8)	−0.0051 (7)	0.0045 (7)	0.0001 (7)
C14	0.1176 (19)	0.0582 (12)	0.0721 (14)	−0.0074 (13)	0.0067 (13)	0.0052 (11)
C15	0.138 (2)	0.0953 (19)	0.0765 (15)	0.0665 (18)	0.0033 (15)	−0.0125 (14)
C16	0.0508 (11)	0.0818 (14)	0.0614 (11)	−0.0004 (10)	0.0048 (9)	−0.0098 (10)
C17	0.0822 (15)	0.0727 (14)	0.0667 (12)	0.0315 (12)	−0.0036 (11)	0.0041 (11)
C18	0.0426 (9)	0.0403 (9)	0.0399 (8)	−0.0025 (7)	0.0017 (7)	−0.0033 (7)
C19	0.0399 (9)	0.0500 (10)	0.0454 (9)	−0.0070 (8)	−0.0016 (7)	−0.0043 (8)
C20	0.0526 (11)	0.0611 (11)	0.0385 (9)	−0.0022 (9)	0.0015 (8)	−0.0008 (8)
C21	0.0577 (12)	0.0703 (12)	0.0519 (10)	−0.0154 (10)	0.0128 (9)	0.0014 (9)
C22	0.0579 (12)	0.0850 (15)	0.0613 (12)	−0.0319 (11)	0.0049 (10)	−0.0076 (10)
C23	0.0585 (12)	0.0747 (13)	0.0447 (9)	−0.0258 (10)	0.0011 (8)	−0.0078 (9)

Geometric parameters (Å, º)

O1—C11	1.368 (2)	C20—C21	1.373 (3)
O1—C12	1.375 (2)	C21—C22	1.366 (3)
O2—C8	1.218 (2)	C22—C23	1.377 (3)
O3—C1	1.221 (2)	C2—H2A	0.9700
O4—C20	1.352 (2)	C2—H2B	0.9700
O4—H4	0.8200	C4—H4A	0.9700
C1—C10	1.455 (2)	C4—H4B	0.9700
C1—C2	1.494 (3)	C5—H5A	0.9700
C2—C3	1.521 (3)	C5—H5B	0.9700
C3—C14	1.525 (3)	C7—H7A	0.9700
C3—C15	1.532 (4)	C7—H7B	0.9700
C3—C4	1.521 (3)	C9—H9	0.9800
C4—C11	1.487 (3)	C14—H14A	0.9600
C5—C12	1.480 (2)	C14—H14B	0.9600
C5—C6	1.529 (3)	C14—H14C	0.9600
C6—C7	1.525 (3)	C15—H15A	0.9600
C6—C17	1.526 (3)	C15—H15B	0.9600
C6—C16	1.521 (3)	C15—H15C	0.9600
C7—C8	1.495 (3)	C16—H16A	0.9600
C8—C13	1.466 (2)	C16—H16B	0.9600
C9—C10	1.503 (2)	C16—H16C	0.9600
C9—C18	1.532 (2)	C17—H17A	0.9600
C9—C13	1.502 (2)	C17—H17B	0.9600
C10—C11	1.333 (2)	C17—H17C	0.9600
C12—C13	1.332 (2)	C19—H19	0.9300
C18—C23	1.376 (3)	C21—H21	0.9300
C18—C19	1.377 (2)	C22—H22	0.9300
C19—C20	1.384 (2)	C23—H23	0.9300
O2···C2^i	3.415 (3)	H4B···H15A	2.3600
O2···C18	3.283 (3)	H5A···H16C	2.4400
O3···O4^ii	2.712 (2)	H5A···H17B	2.5600
O3···C18	3.299 (3)	H5B···H17C	2.4300
O3···C15^iii	3.374 (3)	H5B···O2^x	2.5600
O4···O3^ii	2.712 (2)	H7A···H16A	2.4700
O1···H16C^iv	2.8300	H7A···H17A	2.5700
O2···H17C^v	2.7500	H7B···H17C	2.3800
O2···H2A^i	2.5600	H9···O2	2.5900
O2···H9	2.5900	H9···O3	2.5600
O2···H5B^v	2.5600	H9···H19	2.3700
O3···H4^ii	1.9100	H14A···C1	2.7800
O3···H9	2.5600	H14A···C10	2.8100
C2···O2^vi	3.415 (3)	H14A···C11	2.7600
C10···C14	3.335 (3)	H14B···H2A	2.4700
C11···C23	3.591 (3)	H14B···H15B	2.5200
C12···C23	3.474 (3)	H14C···H4A	2.4200
C13···C16	3.341 (3)	H14C···H15C	2.4500
C14···C10	3.335 (3)	H15A···H2B	2.4400
C15···O3^vii	3.374 (3)	H15A···H4B	2.3600
C16···C13	3.341 (3)	H15B···H2A	2.5300
C18···O3	3.299 (3)	H15B···H14B	2.5200
C18···O2	3.283 (3)	H15B···H19^vi	2.4000
C23···C12	3.474 (3)	H15C···H14C	2.4500
C23···C11	3.591 (3)	H16A···H7A	2.4700
C1···H4^ii	2.9000	H16A···H17A	2.4400
C1···H14A	2.7800	H16B···C8	2.7500
C8···H17C^v	2.9800	H16B···C12	2.7800
C8···H16B	2.7500	H16B···C13	2.8100
C10···H23	3.0100	H16C···H5A	2.4400
C10···H14A	2.8100	H16C···H17B	2.5100
C11···H14A	2.7600	H16C···O1^iv	2.8300
C12···H23	2.9200	H17A···H7A	2.5700
C12···H16B	2.7800	H17A···H16A	2.4400
C12···H2B^viii	2.9700	H17A···C21^xi	3.0400
C13···H23	2.8000	H17A···H21^xi	2.3800
C13···H2B^viii	3.0500	H17B···H5A	2.5600
C13···H16B	2.8100	H17B···H16C	2.5100
C21···H17A^ix	3.0400	H17C···H5B	2.4300
H2A···H14B	2.4700	H17C···H7B	2.3800
H2A···H15B	2.5300	H17C···O2^x	2.7500
H2A···O2^vi	2.5600	H17C···C8^x	2.9800
H2B···H15A	2.4400	H19···H4	2.3400
H2B···C12^viii	2.9700	H19···H9	2.3700
H2B···C13^viii	3.0500	H19···H15B^i	2.4000
H4···H19	2.3400	H21···H17A^ix	2.3800
H4···O3^ii	1.9100	H23···C10	3.0100
H4···C1^ii	2.9000	H23···C12	2.9200
H4A···H14C	2.4200	H23···C13	2.8000
C11—O1—C12	117.76 (12)	C3—C2—H2B	109.00
C20—O4—H4	109.00	H2A—C2—H2B	108.00
O3—C1—C2	122.03 (16)	C3—C4—H4A	109.00
C2—C1—C10	118.05 (15)	C3—C4—H4B	109.00
O3—C1—C10	119.89 (16)	C11—C4—H4A	109.00
C1—C2—C3	114.62 (16)	C11—C4—H4B	109.00
C2—C3—C4	107.95 (16)	H4A—C4—H4B	108.00
C2—C3—C14	110.82 (16)	C6—C5—H5A	109.00
C4—C3—C14	109.81 (17)	C6—C5—H5B	109.00
C4—C3—C15	109.31 (15)	C12—C5—H5A	109.00
C2—C3—C15	109.9 (2)	C12—C5—H5B	109.00
C14—C3—C15	108.98 (18)	H5A—C5—H5B	108.00
C3—C4—C11	111.95 (14)	C6—C7—H7A	109.00
C6—C5—C12	112.03 (14)	C6—C7—H7B	109.00
C5—C6—C7	107.57 (14)	C8—C7—H7A	109.00
C5—C6—C17	109.52 (14)	C8—C7—H7B	109.00
C7—C6—C16	110.55 (14)	H7A—C7—H7B	108.00
C5—C6—C16	110.52 (15)	C10—C9—H9	109.00
C16—C6—C17	108.89 (16)	C13—C9—H9	109.00
C7—C6—C17	109.78 (16)	C18—C9—H9	109.00
C6—C7—C8	114.34 (15)	C3—C14—H14A	109.00
O2—C8—C13	120.10 (15)	C3—C14—H14B	110.00
C7—C8—C13	117.75 (15)	C3—C14—H14C	110.00
O2—C8—C7	122.13 (16)	H14A—C14—H14B	109.00
C10—C9—C18	111.37 (13)	H14A—C14—H14C	109.00
C13—C9—C18	111.40 (13)	H14B—C14—H14C	109.00
C10—C9—C13	107.95 (13)	C3—C15—H15A	109.00
C1—C10—C11	118.37 (15)	C3—C15—H15B	110.00
C9—C10—C11	122.41 (15)	C3—C15—H15C	110.00
C1—C10—C9	119.22 (14)	H15A—C15—H15B	109.00
O1—C11—C4	111.62 (13)	H15A—C15—H15C	109.00
C4—C11—C10	125.91 (15)	H15B—C15—H15C	109.00
O1—C11—C10	122.46 (15)	C6—C16—H16A	109.00
O1—C12—C5	111.55 (13)	C6—C16—H16B	109.00
C5—C12—C13	126.14 (15)	C6—C16—H16C	109.00
O1—C12—C13	122.31 (14)	H16A—C16—H16B	109.00
C8—C13—C12	118.30 (15)	H16A—C16—H16C	109.00
C9—C13—C12	122.41 (14)	H16B—C16—H16C	109.00
C8—C13—C9	119.28 (14)	C6—C17—H17A	109.00
C9—C18—C23	119.90 (14)	C6—C17—H17B	109.00
C19—C18—C23	118.70 (15)	C6—C17—H17C	109.00
C9—C18—C19	121.39 (14)	H17A—C17—H17B	109.00
C18—C19—C20	120.76 (15)	H17A—C17—H17C	109.00
O4—C20—C21	116.34 (16)	H17B—C17—H17C	109.00
C19—C20—C21	119.91 (16)	C18—C19—H19	120.00
O4—C20—C19	123.73 (17)	C20—C19—H19	120.00
C20—C21—C22	119.45 (18)	C20—C21—H21	120.00
C21—C22—C23	120.76 (19)	C22—C21—H21	120.00
C18—C23—C22	120.41 (17)	C21—C22—H22	120.00
C1—C2—H2A	109.00	C23—C22—H22	120.00
C1—C2—H2B	109.00	C18—C23—H23	120.00
C3—C2—H2A	109.00	C22—C23—H23	120.00
C12—O1—C11—C4	−168.18 (13)	C7—C8—C13—C12	0.4 (2)
C12—O1—C11—C10	11.7 (2)	C13—C9—C10—C1	159.00 (14)
C11—O1—C12—C5	168.67 (13)	C13—C9—C10—C11	−20.5 (2)
C11—O1—C12—C13	−11.3 (2)	C18—C9—C10—C1	−78.42 (18)
O3—C1—C2—C3	153.25 (17)	C18—C9—C10—C11	102.04 (18)
C10—C1—C2—C3	−28.8 (2)	C10—C9—C13—C8	−160.59 (14)
O3—C1—C10—C9	−3.8 (2)	C10—C9—C13—C12	20.9 (2)
O3—C1—C10—C11	175.80 (16)	C18—C9—C13—C8	76.84 (18)
C2—C1—C10—C9	178.29 (15)	C18—C9—C13—C12	−101.65 (18)
C2—C1—C10—C11	−2.2 (2)	C10—C9—C18—C19	112.84 (17)
C1—C2—C3—C4	53.2 (2)	C10—C9—C18—C23	−68.39 (19)
C1—C2—C3—C14	−67.1 (2)	C13—C9—C18—C19	−126.58 (16)
C1—C2—C3—C15	172.36 (17)	C13—C9—C18—C23	52.2 (2)
C2—C3—C4—C11	−48.2 (2)	C1—C10—C11—O1	−173.84 (14)
C14—C3—C4—C11	72.8 (2)	C1—C10—C11—C4	6.0 (3)
C15—C3—C4—C11	−167.72 (19)	C9—C10—C11—O1	5.7 (2)
C3—C4—C11—O1	−159.12 (15)	C9—C10—C11—C4	−174.43 (16)
C3—C4—C11—C10	21.0 (2)	O1—C12—C13—C8	174.99 (14)
C12—C5—C6—C7	48.50 (19)	O1—C12—C13—C9	−6.5 (2)
C12—C5—C6—C16	−72.27 (19)	C5—C12—C13—C8	−5.0 (3)
C12—C5—C6—C17	167.77 (15)	C5—C12—C13—C9	173.52 (15)
C6—C5—C12—O1	158.67 (14)	C9—C18—C19—C20	177.82 (16)
C6—C5—C12—C13	−21.4 (2)	C23—C18—C19—C20	−1.0 (3)
C5—C6—C7—C8	−54.23 (19)	C9—C18—C23—C22	−177.92 (17)
C16—C6—C7—C8	66.5 (2)	C19—C18—C23—C22	0.9 (3)
C17—C6—C7—C8	−173.33 (16)	C18—C19—C20—O4	−177.67 (17)
C6—C7—C8—O2	−150.99 (17)	C18—C19—C20—C21	0.6 (3)
C6—C7—C8—C13	30.7 (2)	O4—C20—C21—C22	178.26 (19)
O2—C8—C13—C9	3.5 (2)	C19—C20—C21—C22	−0.1 (3)
O2—C8—C13—C12	−177.95 (16)	C20—C21—C22—C23	0.1 (3)
C7—C8—C13—C9	−178.18 (15)	C21—C22—C23—C18	−0.5 (3)

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, −y, −z+1; (iii) x, −y−1/2, z+1/2; (iv) −x, −y, −z; (v) x, −y+1/2, z+1/2; (vi) −x+1, y−1/2, −z+1/2; (vii) x, −y−1/2, z−1/2; (viii) −x+1, −y, −z; (ix) −x, y−1/2, −z+1/2; (x) x, −y+1/2, z−1/2; (xi) −x, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3^ii	0.8200	1.9100	2.712 (2)	166.00
C2—H2A···O2^vi	0.9700	2.5600	3.415 (3)	147.00
C5—H5B···O2^x	0.9700	2.5600	3.458 (3)	154.00

Symmetry codes: (ii) −x+1, −y, −z+1; (vi) −x+1, y−1/2, −z+1/2; (x) x, −y+1/2, z−1/2.

9-(5-Bromo-2-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydro-2H-xanthene-1,8(5H,9H)-dione (C2)

Crystal data

C24H27BrO4	F(000) = 1904
Mr = 459.36	Dx = 1.376 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4130 reflections
a = 20.6531 (14) Å	θ = 2–26°
b = 9.5629 (7) Å	µ = 1.88 mm^−1
c = 22.4489 (16) Å	T = 290 K
V = 4433.7 (5) Å^3	Prism, colourless
Z = 8	0.2 × 0.2 × 0.1 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	Rint = 0.089
φ and ω scans	θmax = 28.0°, θmin = 1.8°
32126 measured reflections	h = −27→27
5316 independent reflections	k = −12→12
2614 reflections with I > 2σ(I)	l = −29→28

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.13	w = 1/[σ^2(Fo^2) + (0.0482P)^2 + 1.2278P] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.001
5316 reflections	Δρmax = 0.52 e Å^−3
267 parameters	Δρmin = −0.52 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Br1	0.24483 (2)	0.75103 (5)	0.27131 (2)	0.06965 (18)
O1	−0.02129 (9)	0.2488 (2)	0.42152 (11)	0.0513 (6)
O2	0.00374 (12)	0.7364 (3)	0.39969 (12)	0.0649 (7)
C9	0.07037 (15)	0.4742 (3)	0.40184 (15)	0.0381 (8)
H9	0.090731	0.540413	0.429412	0.046*
C10	0.08811 (14)	0.3285 (3)	0.42210 (14)	0.0378 (8)
O4	0.02607 (11)	0.3391 (3)	0.29909 (11)	0.0567 (7)
C12	−0.04215 (15)	0.3842 (4)	0.41513 (15)	0.0438 (9)
C8	−0.03020 (16)	0.6330 (4)	0.40474 (15)	0.0441 (9)
O3	0.19619 (11)	0.3911 (3)	0.43545 (11)	0.0632 (8)
C13	−0.00249 (14)	0.4922 (4)	0.40726 (13)	0.0379 (8)
C20	0.17520 (15)	0.6210 (4)	0.27807 (17)	0.0481 (9)
C18	0.09728 (14)	0.5034 (3)	0.33999 (15)	0.0374 (8)
C5	−0.11458 (14)	0.3912 (4)	0.41748 (17)	0.0572 (11)
H5A	−0.128411	0.391134	0.45877	0.069*
H5B	−0.132423	0.308513	0.39855	0.069*
C3	0.12747 (16)	0.0353 (4)	0.43267 (17)	0.0491 (10)
C11	0.04453 (14)	0.2276 (4)	0.42900 (14)	0.0421 (8)
C4	0.05826 (15)	0.0807 (4)	0.44728 (17)	0.0498 (9)
H4A	0.028141	0.01868	0.427232	0.06*
H4B	0.051198	0.071637	0.489822	0.06*
C6	−0.14119 (16)	0.5206 (4)	0.38675 (16)	0.0512 (10)
C14	0.14179 (17)	−0.1013 (4)	0.46578 (19)	0.0682 (12)
H14A	0.183839	−0.134946	0.45454	0.102*
H14B	0.109678	−0.16979	0.455614	0.102*
H14C	0.140838	−0.084613	0.507943	0.102*
C1	0.15603 (15)	0.2972 (4)	0.43566 (14)	0.0438 (9)
C19	0.14718 (15)	0.5985 (3)	0.33317 (15)	0.0424 (8)
H19	0.162071	0.648022	0.366093	0.051*
C23	0.07549 (16)	0.4317 (4)	0.28981 (16)	0.0440 (9)
C21	0.15365 (19)	0.5503 (4)	0.22899 (18)	0.0590 (11)
H21	0.172652	0.566104	0.192044	0.071*
C7	−0.10317 (15)	0.6463 (4)	0.40967 (16)	0.0544 (10)
H7A	−0.116743	0.728546	0.387659	0.065*
H7B	−0.114301	0.661284	0.451167	0.065*
C2	0.17378 (15)	0.1504 (4)	0.45340 (17)	0.0497 (9)
H2A	0.176605	0.146636	0.496497	0.06*
H2B	0.216526	0.130037	0.437747	0.06*
C15	0.1347 (2)	0.0123 (4)	0.36587 (19)	0.0738 (13)
H15A	0.123806	0.096794	0.345104	0.111*
H15B	0.106247	−0.061499	0.353399	0.111*
H15C	0.178653	−0.013031	0.357011	0.111*
C22	0.10346 (19)	0.4551 (4)	0.23440 (17)	0.0571 (10)
H22	0.088554	0.407003	0.201105	0.069*
C16	−0.21298 (17)	0.5383 (5)	0.4023 (2)	0.0761 (13)
H16A	−0.236844	0.458967	0.387988	0.114*
H16B	−0.229287	0.621803	0.383901	0.114*
H16C	−0.217772	0.545204	0.444726	0.114*
C17	−0.1335 (2)	0.5086 (4)	0.31931 (17)	0.0724 (13)
H17A	−0.088561	0.496978	0.309646	0.109*
H17B	−0.149672	0.591911	0.300681	0.109*
H17C	−0.157506	0.429199	0.305204	0.109*
C24	−0.0006 (2)	0.2674 (5)	0.24921 (19)	0.0859 (16)
H24A	−0.014259	0.334172	0.219861	0.129*
H24B	−0.037084	0.21279	0.261838	0.129*
H24C	0.031642	0.206916	0.232299	0.129*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0485 (2)	0.0613 (3)	0.0991 (4)	−0.0030 (2)	0.0245 (2)	0.0216 (2)
O1	0.0304 (11)	0.0455 (15)	0.0780 (17)	−0.0038 (12)	−0.0022 (11)	0.0152 (14)
O2	0.0599 (16)	0.0423 (16)	0.093 (2)	−0.0059 (14)	0.0024 (15)	−0.0024 (15)
C9	0.0364 (17)	0.038 (2)	0.040 (2)	−0.0063 (14)	0.0008 (15)	0.0003 (15)
C10	0.0327 (17)	0.042 (2)	0.039 (2)	−0.0041 (15)	0.0025 (14)	0.0026 (16)
O4	0.0609 (16)	0.0594 (17)	0.0497 (15)	−0.0173 (14)	0.0028 (12)	−0.0147 (13)
C12	0.0361 (18)	0.051 (2)	0.044 (2)	−0.0007 (17)	−0.0019 (15)	0.0063 (18)
C8	0.047 (2)	0.053 (3)	0.033 (2)	0.0012 (19)	0.0022 (16)	−0.0065 (17)
O3	0.0376 (13)	0.0597 (17)	0.092 (2)	−0.0138 (12)	−0.0117 (13)	0.0134 (16)
C13	0.0349 (17)	0.043 (2)	0.0357 (18)	−0.0014 (15)	0.0004 (15)	0.0015 (16)
C20	0.0392 (19)	0.041 (2)	0.064 (3)	0.0049 (16)	0.0168 (18)	0.013 (2)
C18	0.0372 (17)	0.0340 (18)	0.041 (2)	0.0036 (15)	0.0031 (15)	−0.0013 (17)
C5	0.0333 (19)	0.070 (3)	0.068 (3)	−0.0005 (18)	−0.0020 (17)	0.014 (2)
C3	0.040 (2)	0.042 (2)	0.066 (3)	−0.0022 (16)	0.0106 (18)	0.0079 (19)
C11	0.0298 (16)	0.050 (2)	0.046 (2)	−0.0022 (15)	−0.0001 (14)	0.0084 (17)
C4	0.0351 (18)	0.047 (2)	0.068 (3)	−0.0039 (16)	0.0036 (18)	0.015 (2)
C6	0.0371 (19)	0.063 (3)	0.053 (2)	0.0087 (18)	−0.0056 (17)	0.003 (2)
C14	0.049 (2)	0.048 (2)	0.108 (3)	0.0033 (19)	0.002 (2)	0.013 (2)
C1	0.0323 (17)	0.055 (2)	0.045 (2)	−0.0077 (16)	0.0029 (15)	0.0042 (18)
C19	0.0404 (18)	0.036 (2)	0.051 (2)	0.0008 (15)	0.0064 (17)	0.0033 (17)
C23	0.044 (2)	0.041 (2)	0.047 (2)	0.0026 (17)	0.0052 (17)	−0.0013 (18)
C21	0.063 (3)	0.061 (3)	0.053 (3)	0.011 (2)	0.025 (2)	0.010 (2)
C7	0.049 (2)	0.062 (3)	0.052 (2)	0.0120 (19)	0.0009 (18)	−0.001 (2)
C2	0.0342 (18)	0.051 (2)	0.064 (2)	0.0042 (17)	0.0031 (17)	0.002 (2)
C15	0.078 (3)	0.064 (3)	0.080 (3)	−0.004 (2)	0.010 (3)	−0.014 (2)
C22	0.067 (3)	0.059 (3)	0.046 (3)	0.005 (2)	0.007 (2)	−0.008 (2)
C16	0.044 (2)	0.089 (3)	0.095 (3)	0.012 (2)	−0.006 (2)	0.012 (3)
C17	0.074 (3)	0.088 (3)	0.055 (3)	0.006 (2)	−0.017 (2)	−0.004 (2)
C24	0.086 (3)	0.093 (4)	0.079 (3)	−0.027 (3)	0.007 (3)	−0.041 (3)

Geometric parameters (Å, º)

Br1—C20	1.907 (3)	C4—H4B	0.9700
O1—C12	1.372 (4)	C6—C7	1.526 (5)
O1—C11	1.385 (3)	C6—C17	1.526 (5)
O2—C8	1.218 (4)	C6—C16	1.532 (5)
C9—C10	1.511 (4)	C14—H14A	0.9600
C9—C13	1.519 (4)	C14—H14B	0.9600
C9—C18	1.521 (4)	C14—H14C	0.9600
C9—H9	0.9800	C1—C2	1.504 (5)
C10—C11	1.328 (4)	C19—H19	0.9300
C10—C1	1.466 (4)	C23—C22	1.389 (5)
O4—C23	1.367 (4)	C21—C22	1.385 (5)
O4—C24	1.424 (4)	C21—H21	0.9300
C12—C13	1.330 (4)	C7—H7A	0.9700
C12—C5	1.498 (4)	C7—H7B	0.9700
C8—C13	1.464 (4)	C2—H2A	0.9700
C8—C7	1.516 (4)	C2—H2B	0.9700
O3—C1	1.222 (4)	C15—H15A	0.9600
C20—C21	1.367 (5)	C15—H15B	0.9600
C20—C19	1.383 (4)	C15—H15C	0.9600
C18—C19	1.383 (4)	C22—H22	0.9300
C18—C23	1.393 (4)	C16—H16A	0.9600
C5—C6	1.520 (5)	C16—H16B	0.9600
C5—H5A	0.9700	C16—H16C	0.9600
C5—H5B	0.9700	C17—H17A	0.9600
C3—C15	1.523 (5)	C17—H17B	0.9600
C3—C4	1.529 (4)	C17—H17C	0.9600
C3—C2	1.531 (4)	C24—H24A	0.9600
C3—C14	1.531 (5)	C24—H24B	0.9600
C11—C4	1.491 (4)	C24—H24C	0.9600
C4—H4A	0.9700
C12—O1—C11	117.3 (2)	H14A—C14—H14B	109.5
C10—C9—C13	108.7 (2)	C3—C14—H14C	109.5
C10—C9—C18	110.8 (3)	H14A—C14—H14C	109.5
C13—C9—C18	114.5 (3)	H14B—C14—H14C	109.5
C10—C9—H9	107.5	O3—C1—C10	119.9 (3)
C13—C9—H9	107.5	O3—C1—C2	121.4 (3)
C18—C9—H9	107.5	C10—C1—C2	118.6 (3)
C11—C10—C1	118.4 (3)	C20—C19—C18	120.9 (3)
C11—C10—C9	122.7 (3)	C20—C19—H19	119.6
C1—C10—C9	118.9 (3)	C18—C19—H19	119.6
C23—O4—C24	118.7 (3)	O4—C23—C22	123.5 (3)
C13—C12—O1	123.6 (3)	O4—C23—C18	115.9 (3)
C13—C12—C5	125.8 (3)	C22—C23—C18	120.7 (3)
O1—C12—C5	110.6 (3)	C20—C21—C22	119.9 (3)
O2—C8—C13	121.7 (3)	C20—C21—H21	120.1
O2—C8—C7	120.7 (3)	C22—C21—H21	120.1
C13—C8—C7	117.6 (3)	C8—C7—C6	114.9 (3)
C12—C13—C8	118.6 (3)	C8—C7—H7A	108.5
C12—C13—C9	122.2 (3)	C6—C7—H7A	108.5
C8—C13—C9	119.2 (3)	C8—C7—H7B	108.5
C21—C20—C19	120.5 (3)	C6—C7—H7B	108.5
C21—C20—Br1	120.3 (3)	H7A—C7—H7B	107.5
C19—C20—Br1	119.2 (3)	C1—C2—C3	116.0 (3)
C19—C18—C23	118.3 (3)	C1—C2—H2A	108.3
C19—C18—C9	119.6 (3)	C3—C2—H2A	108.3
C23—C18—C9	122.0 (3)	C1—C2—H2B	108.3
C12—C5—C6	112.4 (3)	C3—C2—H2B	108.3
C12—C5—H5A	109.1	H2A—C2—H2B	107.4
C6—C5—H5A	109.1	C3—C15—H15A	109.5
C12—C5—H5B	109.1	C3—C15—H15B	109.5
C6—C5—H5B	109.1	H15A—C15—H15B	109.5
H5A—C5—H5B	107.9	C3—C15—H15C	109.5
C15—C3—C4	110.1 (3)	H15A—C15—H15C	109.5
C15—C3—C2	110.0 (3)	H15B—C15—H15C	109.5
C4—C3—C2	108.3 (3)	C21—C22—C23	119.7 (4)
C15—C3—C14	109.6 (3)	C21—C22—H22	120.1
C4—C3—C14	108.6 (3)	C23—C22—H22	120.1
C2—C3—C14	110.2 (3)	C6—C16—H16A	109.5
C10—C11—O1	123.0 (3)	C6—C16—H16B	109.5
C10—C11—C4	126.0 (3)	H16A—C16—H16B	109.5
O1—C11—C4	111.0 (3)	C6—C16—H16C	109.5
C11—C4—C3	112.7 (3)	H16A—C16—H16C	109.5
C11—C4—H4A	109.1	H16B—C16—H16C	109.5
C3—C4—H4A	109.1	C6—C17—H17A	109.5
C11—C4—H4B	109.1	C6—C17—H17B	109.5
C3—C4—H4B	109.1	H17A—C17—H17B	109.5
H4A—C4—H4B	107.8	C6—C17—H17C	109.5
C5—C6—C7	107.6 (3)	H17A—C17—H17C	109.5
C5—C6—C17	110.6 (3)	H17B—C17—H17C	109.5
C7—C6—C17	109.9 (3)	O4—C24—H24A	109.5
C5—C6—C16	109.7 (3)	O4—C24—H24B	109.5
C7—C6—C16	109.5 (3)	H24A—C24—H24B	109.5
C17—C6—C16	109.5 (3)	O4—C24—H24C	109.5
C3—C14—H14A	109.5	H24A—C24—H24C	109.5
C3—C14—H14B	109.5	H24B—C24—H24C	109.5
C13—C9—C10—C11	14.6 (4)	C14—C3—C4—C11	166.7 (3)
C18—C9—C10—C11	−112.0 (3)	C12—C5—C6—C7	−48.6 (4)
C13—C9—C10—C1	−164.5 (3)	C12—C5—C6—C17	71.4 (4)
C18—C9—C10—C1	69.0 (4)	C12—C5—C6—C16	−167.7 (3)
C11—O1—C12—C13	9.9 (5)	C11—C10—C1—O3	−172.8 (3)
C11—O1—C12—C5	−170.8 (3)	C9—C10—C1—O3	6.3 (5)
O1—C12—C13—C8	−176.2 (3)	C11—C10—C1—C2	3.4 (5)
C5—C12—C13—C8	4.7 (5)	C9—C10—C1—C2	−177.6 (3)
O1—C12—C13—C9	2.8 (5)	C21—C20—C19—C18	0.6 (5)
C5—C12—C13—C9	−176.3 (3)	Br1—C20—C19—C18	−179.0 (2)
O2—C8—C13—C12	177.4 (3)	C23—C18—C19—C20	−0.6 (5)
C7—C8—C13—C12	−1.6 (5)	C9—C18—C19—C20	176.1 (3)
O2—C8—C13—C9	−1.6 (5)	C24—O4—C23—C22	−3.2 (5)
C7—C8—C13—C9	179.4 (3)	C24—O4—C23—C18	177.0 (3)
C10—C9—C13—C12	−14.1 (4)	C19—C18—C23—O4	−179.9 (3)
C18—C9—C13—C12	110.3 (3)	C9—C18—C23—O4	3.4 (5)
C10—C9—C13—C8	164.9 (3)	C19—C18—C23—C22	0.2 (5)
C18—C9—C13—C8	−70.7 (4)	C9—C18—C23—C22	−176.4 (3)
C10—C9—C18—C19	−110.5 (3)	C19—C20—C21—C22	−0.2 (6)
C13—C9—C18—C19	126.2 (3)	Br1—C20—C21—C22	179.4 (3)
C10—C9—C18—C23	66.2 (4)	O2—C8—C7—C6	152.3 (3)
C13—C9—C18—C23	−57.1 (4)	C13—C8—C7—C6	−28.7 (4)
C13—C12—C5—C6	22.4 (5)	C5—C6—C7—C8	52.9 (4)
O1—C12—C5—C6	−156.8 (3)	C17—C6—C7—C8	−67.6 (4)
C1—C10—C11—O1	175.3 (3)	C16—C6—C7—C8	172.0 (3)
C9—C10—C11—O1	−3.7 (5)	O3—C1—C2—C3	−160.4 (3)
C1—C10—C11—C4	−2.6 (5)	C10—C1—C2—C3	23.5 (4)
C9—C10—C11—C4	178.4 (3)	C15—C3—C2—C1	72.7 (4)
C12—O1—C11—C10	−9.5 (5)	C4—C3—C2—C1	−47.7 (4)
C12—O1—C11—C4	168.7 (3)	C14—C3—C2—C1	−166.4 (3)
C10—C11—C4—C3	−24.5 (5)	C20—C21—C22—C23	−0.2 (6)
O1—C11—C4—C3	157.3 (3)	O4—C23—C22—C21	−179.6 (3)
C15—C3—C4—C11	−73.3 (4)	C18—C23—C22—C21	0.2 (6)
C2—C3—C4—C11	47.0 (4)

3,3,6,6-Tetramethyl-9-(pyridin-2-yl)-3,4,6,7-tetrahydro-2H-xanthene-1,8(5H,9H)-dione (C3)

Crystal data

C22H25NO3	Z = 4
Mr = 351.43	F(000) = 752
Triclinic, P1	Dx = 1.214 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2893 (11) Å	Cell parameters from 5671 reflections
b = 10.0558 (12) Å	θ = 2.3–26.1°
c = 22.911 (3) Å	µ = 0.08 mm^−1
α = 83.057 (2)°	T = 290 K
β = 85.272 (2)°	Prism, colourless
γ = 64.888 (2)°	0.45 × 0.3 × 0.2 mm
V = 1922.5 (4) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	5317 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 25.5°, θmin = 0.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
Tmin = 0.917, Tmax = 0.984	k = −12→12
18985 measured reflections	l = −27→27
7118 independent reflections

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.223	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0744P)^2 + 2.8721P] where P = (Fo^2 + 2Fc^2)/3
7118 reflections	(Δ/σ)max < 0.001
477 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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 > 2sigma(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
O1	0.8298 (3)	0.3350 (3)	0.01340 (10)	0.0415 (7)
O2	1.3557 (3)	0.2554 (4)	0.04621 (14)	0.0698 (11)
O3	0.8829 (3)	0.4760 (3)	0.19619 (12)	0.0638 (10)
N1	1.0840 (4)	0.0756 (3)	0.13486 (14)	0.0515 (11)
C1	0.7996 (4)	0.4636 (4)	0.16077 (15)	0.0407 (11)
C2	0.6209 (4)	0.5280 (4)	0.16931 (15)	0.0425 (11)
C3	0.5395 (4)	0.4544 (4)	0.13697 (15)	0.0416 (11)
C4	0.5982 (4)	0.4481 (4)	0.07294 (15)	0.0416 (11)
C5	1.0282 (4)	0.2407 (4)	−0.06113 (15)	0.0460 (11)
C6	1.2034 (4)	0.1299 (4)	−0.06901 (16)	0.0449 (11)
C7	1.3071 (4)	0.1938 (4)	−0.04509 (17)	0.0494 (12)
C8	1.2599 (4)	0.2453 (4)	0.01534 (16)	0.0436 (11)
C9	1.0497 (4)	0.3248 (4)	0.09889 (14)	0.0369 (10)
C10	0.8709 (4)	0.3930 (3)	0.10693 (14)	0.0357 (10)
C11	0.7750 (4)	0.3909 (3)	0.06669 (14)	0.0358 (10)
C12	0.9900 (4)	0.2885 (3)	−0.00085 (14)	0.0371 (10)
C13	1.0941 (4)	0.2882 (3)	0.03623 (14)	0.0369 (10)
C14	0.5788 (5)	0.2988 (4)	0.16621 (18)	0.0552 (14)
C15	0.3587 (4)	0.5450 (5)	0.13902 (19)	0.0594 (15)
C16	1.2447 (5)	0.1085 (5)	−0.13378 (18)	0.0625 (16)
C17	1.2269 (5)	−0.0176 (4)	−0.0344 (2)	0.0602 (14)
C18	1.1262 (4)	0.1843 (4)	0.14041 (14)	0.0396 (10)
C19	1.2360 (4)	0.1713 (5)	0.18031 (17)	0.0553 (14)
C20	1.3076 (5)	0.0377 (6)	0.21449 (19)	0.0722 (16)
C21	1.2657 (5)	−0.0745 (5)	0.20901 (19)	0.0673 (16)
C22	1.1521 (5)	−0.0498 (4)	0.16959 (19)	0.0629 (14)
O1'	0.3287 (3)	0.3393 (3)	0.48013 (10)	0.0445 (8)
O2'	0.4098 (3)	0.5772 (3)	0.29928 (12)	0.0650 (10)
O3'	0.8558 (3)	0.2917 (4)	0.44994 (14)	0.0751 (11)
N1'	0.6018 (4)	0.1459 (4)	0.35997 (15)	0.0595 (11)
C1'	0.7543 (4)	0.2653 (4)	0.48008 (17)	0.0476 (12)
C2'	0.7904 (5)	0.1877 (4)	0.54091 (17)	0.0519 (12)
C3'	0.6877 (4)	0.1053 (4)	0.56376 (16)	0.0464 (12)
C4'	0.5127 (4)	0.2142 (4)	0.55524 (15)	0.0472 (11)
C5'	0.1078 (4)	0.4774 (4)	0.42081 (16)	0.0452 (11)
C6'	0.0632 (4)	0.5136 (4)	0.35608 (16)	0.0457 (11)
C7'	0.1448 (4)	0.6093 (4)	0.32612 (16)	0.0495 (12)
C8'	0.3220 (4)	0.5445 (4)	0.33432 (15)	0.0434 (11)
C9'	0.5619 (4)	0.3765 (4)	0.39586 (15)	0.0384 (10)
C10'	0.5945 (4)	0.3133 (4)	0.45894 (14)	0.0381 (10)
C11'	0.4849 (4)	0.2912 (4)	0.49536 (15)	0.0401 (10)
C12'	0.2822 (4)	0.4217 (3)	0.42747 (15)	0.0377 (10)
C13'	0.3841 (4)	0.4468 (3)	0.38770 (14)	0.0372 (10)
C14'	0.7265 (5)	−0.0264 (4)	0.5290 (2)	0.0653 (16)
C15'	0.7162 (6)	0.0538 (5)	0.62929 (19)	0.0711 (17)
C16'	0.1156 (5)	0.3725 (5)	0.3263 (2)	0.0653 (16)
C17'	−0.1185 (4)	0.5999 (5)	0.3527 (2)	0.0673 (16)
C18'	0.6479 (4)	0.2558 (4)	0.35482 (14)	0.0397 (10)
C19'	0.7696 (4)	0.2597 (5)	0.31667 (17)	0.0553 (14)
C20'	0.8508 (5)	0.1419 (6)	0.28370 (19)	0.0701 (18)
C21'	0.8071 (5)	0.0265 (5)	0.2892 (2)	0.0719 (17)
C22'	0.6803 (6)	0.0341 (5)	0.3265 (2)	0.0708 (16)
H2A	0.59452	0.51948	0.21104	0.0510*
H2B	0.57794	0.63226	0.15575	0.0510*
H4A	0.55052	0.54620	0.05250	0.0499*
H4B	0.56394	0.38493	0.05451	0.0499*
H5A	1.00698	0.32650	−0.08925	0.0551*
H5B	0.95937	0.19531	−0.06943	0.0551*
H7A	1.30516	0.27641	−0.07220	0.0590*
H7B	1.41593	0.11921	−0.04446	0.0590*
H9	1.09002	0.39614	0.10700	0.0443*
H14A	0.69199	0.24193	0.16489	0.0824*
H14B	0.54026	0.30401	0.20643	0.0824*
H14C	0.52897	0.25270	0.14568	0.0824*
H15A	0.31934	0.54638	0.17913	0.0893*
H15B	0.30942	0.50112	0.11697	0.0893*
H15C	0.33398	0.64407	0.12223	0.0893*
H16A	1.18403	0.06238	−0.14777	0.0937*
H16B	1.21991	0.20255	−0.15579	0.0937*
H16C	1.35611	0.04684	−0.13871	0.0937*
H17A	1.33512	−0.08776	−0.03958	0.0901*
H17B	1.20333	−0.00381	0.00663	0.0901*
H17C	1.15686	−0.05363	−0.04847	0.0901*
H19	1.26144	0.24974	0.18422	0.0666*
H20	1.38390	0.02495	0.24106	0.0865*
H21	1.31276	−0.16482	0.23130	0.0808*
H22	1.12036	−0.12481	0.16678	0.0754*
H5A'	0.05325	0.56549	0.44127	0.0538*
H5B'	0.07244	0.40354	0.43884	0.0538*
H2B'	0.77645	0.25990	0.56787	0.0620*
H2A'	0.90123	0.11765	0.54125	0.0620*
H4B'	0.44616	0.16093	0.56290	0.0565*
H4A'	0.48175	0.28668	0.58358	0.0565*
H7A'	0.12570	0.62490	0.28433	0.0591*
H7B'	0.09644	0.70495	0.34156	0.0591*
H9'	0.60208	0.45281	0.38724	0.0461*
H14D	0.70954	0.00688	0.48801	0.0983*
H14E	0.65879	−0.07467	0.54290	0.0983*
H14F	0.83568	−0.09449	0.53411	0.0983*
H15D	0.82666	−0.01002	0.63449	0.1061*
H15E	0.68698	0.13798	0.65100	0.1061*
H15F	0.65283	0.00129	0.64339	0.1061*
H16D	0.08591	0.39667	0.28590	0.0978*
H16E	0.06506	0.31302	0.34603	0.0978*
H16F	0.22900	0.31874	0.32803	0.0978*
H17D	−0.15200	0.68931	0.37141	0.1010*
H17E	−0.16948	0.54068	0.37242	0.1010*
H17F	−0.14743	0.62361	0.31227	0.1010*
H19'	0.79613	0.33969	0.31329	0.0661*
H20'	0.93423	0.14076	0.25806	0.0841*
H21'	0.86186	−0.05507	0.26816	0.0864*
H22'	0.64752	−0.04184	0.32867	0.0853*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0291 (11)	0.0497 (14)	0.0404 (13)	−0.0089 (10)	−0.0041 (9)	−0.0116 (10)
O2	0.0396 (15)	0.102 (2)	0.073 (2)	−0.0315 (16)	0.0011 (14)	−0.0225 (17)
O3	0.0481 (15)	0.085 (2)	0.0590 (17)	−0.0221 (15)	−0.0062 (13)	−0.0288 (15)
N1	0.0560 (19)	0.0396 (17)	0.0528 (19)	−0.0124 (15)	−0.0111 (15)	−0.0046 (14)
C1	0.0389 (18)	0.0417 (19)	0.0393 (18)	−0.0140 (15)	−0.0025 (15)	−0.0063 (14)
C2	0.0384 (18)	0.0439 (19)	0.0401 (18)	−0.0120 (15)	0.0040 (14)	−0.0090 (15)
C3	0.0287 (16)	0.0430 (19)	0.048 (2)	−0.0097 (14)	−0.0016 (14)	−0.0054 (15)
C4	0.0311 (17)	0.0431 (19)	0.0432 (19)	−0.0069 (14)	−0.0082 (14)	−0.0057 (15)
C5	0.0412 (19)	0.046 (2)	0.043 (2)	−0.0099 (16)	−0.0029 (15)	−0.0071 (16)
C6	0.0419 (19)	0.0405 (19)	0.048 (2)	−0.0134 (16)	0.0050 (15)	−0.0072 (15)
C7	0.042 (2)	0.048 (2)	0.056 (2)	−0.0183 (17)	0.0096 (17)	−0.0063 (17)
C8	0.0375 (18)	0.044 (2)	0.049 (2)	−0.0177 (16)	−0.0001 (16)	−0.0015 (16)
C9	0.0313 (16)	0.0366 (17)	0.0438 (18)	−0.0144 (14)	−0.0029 (14)	−0.0060 (14)
C10	0.0312 (16)	0.0324 (17)	0.0400 (18)	−0.0098 (13)	−0.0019 (13)	−0.0034 (13)
C11	0.0338 (17)	0.0312 (16)	0.0379 (17)	−0.0086 (13)	−0.0030 (14)	−0.0044 (13)
C12	0.0323 (16)	0.0330 (17)	0.0389 (18)	−0.0073 (13)	−0.0024 (14)	−0.0005 (13)
C13	0.0321 (16)	0.0330 (17)	0.0420 (18)	−0.0109 (13)	−0.0005 (14)	−0.0011 (14)
C14	0.047 (2)	0.055 (2)	0.064 (3)	−0.0228 (19)	−0.0015 (18)	−0.0022 (19)
C15	0.0339 (19)	0.069 (3)	0.065 (3)	−0.0102 (18)	0.0045 (18)	−0.016 (2)
C16	0.061 (3)	0.066 (3)	0.058 (2)	−0.023 (2)	0.014 (2)	−0.021 (2)
C17	0.057 (2)	0.041 (2)	0.074 (3)	−0.0132 (18)	0.007 (2)	−0.0080 (19)
C18	0.0272 (16)	0.0449 (19)	0.0390 (18)	−0.0076 (14)	−0.0019 (13)	−0.0034 (14)
C19	0.043 (2)	0.075 (3)	0.048 (2)	−0.025 (2)	−0.0110 (17)	0.0013 (19)
C20	0.049 (2)	0.105 (4)	0.047 (2)	−0.020 (3)	−0.0173 (19)	0.014 (2)
C21	0.061 (3)	0.061 (3)	0.050 (2)	−0.001 (2)	−0.002 (2)	0.011 (2)
C22	0.071 (3)	0.043 (2)	0.058 (2)	−0.008 (2)	−0.004 (2)	−0.0028 (18)
O1'	0.0340 (12)	0.0481 (14)	0.0464 (14)	−0.0153 (11)	0.0001 (10)	0.0060 (11)
O2'	0.0489 (16)	0.0708 (19)	0.0591 (17)	−0.0178 (14)	0.0073 (13)	0.0196 (14)
O3'	0.0441 (16)	0.099 (2)	0.084 (2)	−0.0376 (16)	−0.0105 (15)	0.0194 (18)
N1'	0.061 (2)	0.0468 (19)	0.065 (2)	−0.0185 (16)	0.0149 (17)	−0.0120 (16)
C1'	0.042 (2)	0.048 (2)	0.055 (2)	−0.0206 (17)	−0.0051 (17)	−0.0040 (17)
C2'	0.052 (2)	0.055 (2)	0.053 (2)	−0.0251 (19)	−0.0165 (18)	−0.0009 (18)
C3'	0.045 (2)	0.044 (2)	0.046 (2)	−0.0141 (16)	−0.0101 (16)	0.0000 (16)
C4'	0.049 (2)	0.047 (2)	0.0412 (19)	−0.0166 (17)	−0.0025 (16)	−0.0009 (16)
C5'	0.0311 (17)	0.047 (2)	0.051 (2)	−0.0114 (15)	0.0043 (15)	−0.0039 (16)
C6'	0.0324 (18)	0.044 (2)	0.052 (2)	−0.0086 (15)	−0.0040 (15)	0.0003 (16)
C7'	0.045 (2)	0.044 (2)	0.046 (2)	−0.0076 (16)	−0.0053 (16)	0.0057 (16)
C8'	0.0409 (19)	0.0379 (19)	0.0434 (19)	−0.0105 (15)	0.0036 (15)	−0.0012 (15)
C9'	0.0326 (17)	0.0366 (17)	0.0456 (19)	−0.0156 (14)	0.0014 (14)	0.0004 (14)
C10'	0.0378 (18)	0.0362 (17)	0.0389 (18)	−0.0141 (14)	−0.0025 (14)	−0.0028 (14)
C11'	0.0337 (17)	0.0354 (18)	0.0458 (19)	−0.0088 (14)	−0.0010 (14)	−0.0058 (14)
C12'	0.0326 (17)	0.0322 (17)	0.0435 (18)	−0.0095 (14)	0.0008 (14)	−0.0026 (14)
C13'	0.0332 (17)	0.0328 (17)	0.0396 (18)	−0.0093 (14)	0.0013 (14)	−0.0010 (13)
C14'	0.063 (3)	0.042 (2)	0.082 (3)	−0.012 (2)	−0.010 (2)	−0.006 (2)
C15'	0.077 (3)	0.074 (3)	0.056 (3)	−0.028 (3)	−0.019 (2)	0.014 (2)
C16'	0.055 (2)	0.058 (3)	0.080 (3)	−0.017 (2)	−0.017 (2)	−0.012 (2)
C17'	0.037 (2)	0.067 (3)	0.082 (3)	−0.0084 (19)	−0.010 (2)	0.006 (2)
C18'	0.0313 (17)	0.0423 (19)	0.0380 (18)	−0.0098 (14)	−0.0028 (14)	0.0031 (14)
C19'	0.0363 (19)	0.073 (3)	0.051 (2)	−0.0187 (19)	0.0045 (16)	−0.0060 (19)
C20'	0.045 (2)	0.090 (4)	0.055 (3)	−0.010 (2)	0.0125 (19)	−0.012 (2)
C21'	0.065 (3)	0.060 (3)	0.058 (3)	0.007 (2)	0.004 (2)	−0.017 (2)
C22'	0.085 (3)	0.046 (2)	0.070 (3)	−0.017 (2)	0.010 (2)	−0.012 (2)

Geometric parameters (Å, º)

O1—C11	1.374 (4)	C17—H17A	0.9600
O1—C12	1.381 (5)	C17—H17B	0.9600
O2—C8	1.225 (5)	C19—H19	0.9300
O3—C1	1.218 (5)	C20—H20	0.9300
O1'—C11'	1.381 (5)	C21—H21	0.9300
O1'—C12'	1.367 (4)	C22—H22	0.9300
O2'—C8'	1.214 (5)	C1'—C2'	1.502 (5)
O3'—C1'	1.224 (5)	C1'—C10'	1.458 (6)
N1—C22	1.337 (5)	C2'—C3'	1.534 (6)
N1—C18	1.331 (5)	C3'—C4'	1.539 (6)
N1'—C22'	1.343 (6)	C3'—C14'	1.523 (5)
N1'—C18'	1.334 (5)	C3'—C15'	1.534 (6)
C1—C10	1.464 (5)	C4'—C11'	1.477 (5)
C1—C2	1.509 (6)	C5'—C6'	1.532 (5)
C2—C3	1.539 (5)	C5'—C12'	1.487 (6)
C3—C4	1.521 (5)	C6'—C7'	1.532 (6)
C3—C14	1.527 (5)	C6'—C16'	1.520 (6)
C3—C15	1.534 (6)	C6'—C17'	1.540 (6)
C4—C11	1.493 (6)	C7'—C8'	1.510 (6)
C5—C6	1.544 (6)	C8'—C13'	1.462 (5)
C5—C12	1.483 (5)	C9'—C10'	1.507 (5)
C6—C7	1.529 (6)	C9'—C13'	1.514 (6)
C6—C16	1.520 (6)	C9'—C18'	1.525 (5)
C6—C17	1.532 (5)	C10'—C11'	1.338 (5)
C7—C8	1.503 (5)	C12'—C13'	1.340 (5)
C8—C13	1.467 (6)	C18'—C19'	1.382 (6)
C9—C18	1.530 (5)	C19'—C20'	1.381 (7)
C9—C10	1.509 (5)	C20'—C21'	1.372 (7)
C9—C13	1.506 (5)	C21'—C22'	1.377 (7)
C10—C11	1.342 (5)	C2'—H2B'	0.9700
C12—C13	1.338 (5)	C2'—H2A'	0.9700
C18—C19	1.380 (6)	C4'—H4B'	0.9700
C19—C20	1.391 (7)	C4'—H4A'	0.9700
C20—C21	1.362 (7)	C5'—H5A'	0.9700
C21—C22	1.368 (7)	C5'—H5B'	0.9700
C2—H2A	0.9700	C7'—H7A'	0.9700
C2—H2B	0.9700	C7'—H7B'	0.9700
C4—H4A	0.9700	C9'—H9'	0.9800
C4—H4B	0.9700	C14'—H14D	0.9600
C5—H5B	0.9700	C14'—H14E	0.9600
C5—H5A	0.9700	C14'—H14F	0.9600
C7—H7A	0.9700	C15'—H15D	0.9600
C7—H7B	0.9700	C15'—H15E	0.9600
C9—H9	0.9800	C15'—H15F	0.9600
C14—H14A	0.9600	C16'—H16D	0.9600
C14—H14C	0.9600	C16'—H16E	0.9600
C14—H14B	0.9600	C16'—H16F	0.9600
C15—H15A	0.9600	C17'—H17D	0.9600
C15—H15C	0.9600	C17'—H17E	0.9600
C15—H15B	0.9600	C17'—H17F	0.9600
C16—H16C	0.9600	C19'—H19'	0.9300
C16—H16B	0.9600	C20'—H20'	0.9300
C16—H16A	0.9600	C21'—H21'	0.9300
C17—H17C	0.9600	C22'—H22'	0.9300
O2···C18	3.143 (5)	H7A'···H17F	2.5700
O2···C19	3.316 (5)	H7A'···H16D	2.4700
O2'···C2	3.395 (5)	H7A···C1^vii	2.9600
O2'···C18'	3.219 (5)	H7A···H16B	2.4400
O3···C18	3.186 (5)	H7A···H2B^vii	2.4000
O3'···C19'	3.306 (5)	H7A···C2^vii	3.0200
O3'···C18'	3.176 (5)	H7A···C10^vii	3.0500
O1···H17C^i	2.8000	H7B···H16C	2.5300
O1'···H14E^ii	2.7300	H7B···H17A	2.4800
O2···H9	2.6400	H7B'···H17D	2.4200
O2···H17A^iii	2.6400	H9···O2	2.6400
O2···H4B^iv	2.7800	H9···O3	2.6400
O2···H14C^iv	2.8900	H9···H19	2.3800
O2'···H2A	2.5000	H9···H5A^vii	2.5300
O2'···H21^v	2.6900	H9'···O2'	2.6300
O2'···H9'	2.6300	H9'···O3'	2.6500
O3···H9	2.6400	H9'···H19'	2.3700
O3···H16D^iv	2.7200	H9'···H4A'^viii	2.5500
O3'···H5B'^iv	2.6700	H14A···C10	2.8500
O3'···H9'	2.6500	H14A···C11	2.7900
O3'···H17E^iv	2.8200	H14A···C1	2.7900
O3'···H14F^vi	2.7300	H14A···C20'	3.0600
C2···O2'	3.395 (5)	H14B···H15A	2.4800
C10···C14	3.372 (6)	H14B···H2A	2.4400
C10'···C14'	3.346 (5)	H14C···H4B	2.4100
C13···C17	3.354 (5)	H14C···O2^x	2.8900
C13'···C16'	3.343 (6)	H14C···H15B	2.5200
C14···C10	3.372 (6)	H14C···H19^x	2.5800
C14···C20'	3.582 (7)	H14D···C11'	2.7500
C14'···C10'	3.346 (5)	H14D···C1'	2.7800
C15'···C20^vi	3.599 (6)	H14D···C10'	2.8100
C16'···C13'	3.343 (6)	H14E···H15F	2.5000
C17···C13	3.354 (5)	H14E···H4B'	2.4200
C18···O2	3.143 (5)	H14E···O1'^ii	2.7300
C18···O3	3.186 (5)	H14F···H2A'	2.4800
C18'···O2'	3.219 (5)	H14F···H15D	2.5300
C18'···O3'	3.176 (5)	H14F···O3'^vi	2.7300
C19···O2	3.316 (5)	H15A···H14B	2.4800
C19'···O3'	3.306 (5)	H15B···H4B	2.5500
C20···C15'^vi	3.599 (6)	H15B···H14C	2.5200
C20'···C14	3.582 (7)	H15C···H4A	2.4000
C1···H14A	2.7900	H15C···H22^v	2.5900
C1···H7A^vii	2.9600	H15C···C22^v	3.1000
C1'···H14D	2.7800	H15C···H2B	2.4000
C2···H7A^vii	3.0200	H15D···H14F	2.5300
C8···H17B	2.8000	H15D···H2A'	2.5600
C8'···H2B'^viii	2.9900	H15E···H2B'	2.4200
C8'···H16F	2.7700	H15E···H4A'	2.4000
C10···H14A	2.8500	H15F···H14E	2.5000
C10···H7A^vii	3.0500	H16A···H17C	2.4700
C10'···H14D	2.8100	H16B···H7A	2.4400
C11···H14A	2.7900	H16B···H5A	2.3800
C11'···H14D	2.7500	H16C···H17A	2.5400
C12···H17B	2.7500	H16C···H7B	2.5300
C12'···H2B'^viii	3.0300	H16D···H7A'	2.4700
C12'···H16F	2.7700	H16D···H17F	2.4900
C13···H17B	2.8200	H16D···O3^x	2.7200
C13'···H2B'^viii	2.9500	H16E···H19'^x	2.5600
C13'···H16F	2.8200	H16E···H5B'	2.4300
C20'···H14A	3.0600	H16E···H17E	2.5000
C22···H20'	2.9700	H16F···C13'	2.8200
C22···H15C^ix	3.1000	H16F···C8'	2.7700
H5A'···H17D	2.4000	H16F···C12'	2.7700
H5B'···O3'^x	2.6700	H17A···H16C	2.5400
H5B'···H16E	2.4300	H17A···H7B	2.4800
H5B'···H17E	2.5900	H17A···O2^iii	2.6400
H2A···O2'	2.5000	H17B···C8	2.8000
H2A···H14B	2.4400	H17B···C12	2.7500
H2B···H15C	2.4000	H17B···C13	2.8200
H2B···H7A^vii	2.4000	H17C···O1^i	2.8000
H2B'···H15E	2.4200	H17C···H5B	2.4100
H2B'···C12'^viii	3.0300	H17C···H16A	2.4700
H2B'···C13'^viii	2.9500	H17D···H7B'	2.4200
H2B'···C8'^viii	2.9900	H17D···H5A'	2.4000
H2A'···H15D	2.5600	H17E···O3'^x	2.8200
H2A'···H14F	2.4800	H17E···H5B'	2.5900
H4A···H15C	2.4000	H17E···H16E	2.5000
H4B···H14C	2.4100	H17F···H16D	2.4900
H4B···O2^x	2.7800	H17F···H7A'	2.5700
H4B···H15B	2.5500	H19···H9	2.3800
H4B'···H14E	2.4200	H19···H14C^iv	2.5800
H5A···H16B	2.3800	H19'···H16E^iv	2.5600
H5A···H9^vii	2.5300	H19'···H9'	2.3700
H5B···H17C	2.4100	H20'···C22	2.9700
H4A'···H15E	2.4000	H21···O2'^ix	2.6900
H4A'···H9'^viii	2.5500	H22···H15C^ix	2.5900
C11—O1—C12	118.0 (3)	C21—C22—H22	118.00
C11'—O1'—C12'	118.5 (3)	N1—C22—H22	118.00
C18—N1—C22	117.7 (4)	O3'—C1'—C2'	120.4 (4)
C18'—N1'—C22'	117.3 (4)	O3'—C1'—C10'	121.1 (4)
O3—C1—C10	120.3 (4)	C2'—C1'—C10'	118.5 (4)
O3—C1—C2	121.2 (3)	C1'—C2'—C3'	114.9 (4)
C2—C1—C10	118.5 (3)	C2'—C3'—C4'	107.3 (3)
C1—C2—C3	114.4 (3)	C2'—C3'—C14'	110.5 (3)
C2—C3—C4	109.1 (3)	C2'—C3'—C15'	109.6 (4)
C4—C3—C14	110.1 (3)	C4'—C3'—C14'	109.2 (3)
C4—C3—C15	108.6 (3)	C4'—C3'—C15'	109.9 (3)
C14—C3—C15	109.4 (3)	C14'—C3'—C15'	110.2 (3)
C2—C3—C14	109.6 (3)	C3'—C4'—C11'	112.5 (3)
C2—C3—C15	110.1 (3)	C6'—C5'—C12'	111.9 (3)
C3—C4—C11	112.3 (3)	C5'—C6'—C7'	108.1 (3)
C6—C5—C12	112.3 (3)	C5'—C6'—C16'	110.3 (3)
C5—C6—C16	110.0 (3)	C5'—C6'—C17'	109.0 (3)
C5—C6—C7	107.6 (3)	C7'—C6'—C16'	110.6 (3)
C7—C6—C17	110.5 (3)	C7'—C6'—C17'	109.6 (3)
C16—C6—C17	109.9 (3)	C16'—C6'—C17'	109.2 (4)
C5—C6—C17	108.9 (3)	C6'—C7'—C8'	114.2 (3)
C7—C6—C16	110.0 (3)	O2'—C8'—C7'	121.4 (3)
C6—C7—C8	115.6 (3)	O2'—C8'—C13'	120.7 (4)
O2—C8—C13	120.2 (3)	C7'—C8'—C13'	117.8 (3)
O2—C8—C7	121.3 (4)	C10'—C9'—C13'	109.1 (3)
C7—C8—C13	118.5 (3)	C10'—C9'—C18'	110.0 (3)
C13—C9—C18	109.3 (3)	C13'—C9'—C18'	111.6 (3)
C10—C9—C18	111.4 (3)	C1'—C10'—C9'	118.9 (3)
C10—C9—C13	109.2 (3)	C1'—C10'—C11'	118.5 (3)
C1—C10—C9	118.7 (3)	C9'—C10'—C11'	122.5 (4)
C1—C10—C11	118.8 (3)	O1'—C11'—C4'	111.8 (3)
C9—C10—C11	122.5 (3)	O1'—C11'—C10'	122.6 (3)
O1—C11—C4	111.2 (3)	C4'—C11'—C10'	125.7 (4)
C4—C11—C10	125.6 (3)	O1'—C12'—C5'	111.5 (3)
O1—C11—C10	123.2 (3)	O1'—C12'—C13'	123.0 (3)
O1—C12—C13	122.8 (3)	C5'—C12'—C13'	125.5 (3)
O1—C12—C5	111.4 (3)	C8'—C13'—C9'	118.7 (3)
C5—C12—C13	125.8 (3)	C8'—C13'—C12'	119.1 (3)
C8—C13—C12	118.3 (3)	C9'—C13'—C12'	122.2 (3)
C8—C13—C9	118.8 (3)	N1'—C18'—C9'	115.7 (3)
C9—C13—C12	122.9 (3)	N1'—C18'—C19'	123.2 (4)
C9—C18—C19	121.1 (4)	C9'—C18'—C19'	121.1 (4)
N1—C18—C9	116.5 (3)	C18'—C19'—C20'	118.4 (4)
N1—C18—C19	122.4 (3)	C19'—C20'—C21'	119.3 (4)
C18—C19—C20	118.2 (4)	C20'—C21'—C22'	118.6 (4)
C19—C20—C21	119.9 (4)	N1'—C22'—C21'	123.2 (5)
C20—C21—C22	117.8 (4)	C1'—C2'—H2B'	109.00
N1—C22—C21	124.0 (4)	C1'—C2'—H2A'	109.00
C1—C2—H2B	109.00	C3'—C2'—H2B'	109.00
C1—C2—H2A	109.00	C3'—C2'—H2A'	109.00
H2A—C2—H2B	108.00	H2B'—C2'—H2A'	108.00
C3—C2—H2A	109.00	C3'—C4'—H4B'	109.00
C3—C2—H2B	109.00	C3'—C4'—H4A'	109.00
C3—C4—H4A	109.00	C11'—C4'—H4B'	109.00
C11—C4—H4B	109.00	C11'—C4'—H4A'	109.00
C3—C4—H4B	109.00	H4B'—C4'—H4A'	108.00
C11—C4—H4A	109.00	C6'—C5'—H5A'	109.00
H4A—C4—H4B	108.00	C6'—C5'—H5B'	109.00
C12—C5—H5A	109.00	C12'—C5'—H5A'	109.00
C12—C5—H5B	109.00	C12'—C5'—H5B'	109.00
C6—C5—H5B	109.00	H5A'—C5'—H5B'	108.00
C6—C5—H5A	109.00	C6'—C7'—H7A'	109.00
H5A—C5—H5B	108.00	C6'—C7'—H7B'	109.00
C6—C7—H7B	108.00	C8'—C7'—H7A'	109.00
C6—C7—H7A	108.00	C8'—C7'—H7B'	109.00
H7A—C7—H7B	107.00	H7A'—C7'—H7B'	108.00
C8—C7—H7A	108.00	C10'—C9'—H9'	109.00
C8—C7—H7B	108.00	C13'—C9'—H9'	109.00
C10—C9—H9	109.00	C18'—C9'—H9'	109.00
C13—C9—H9	109.00	C3'—C14'—H14D	109.00
C18—C9—H9	109.00	C3'—C14'—H14E	110.00
C3—C14—H14A	109.00	C3'—C14'—H14F	110.00
H14A—C14—H14B	109.00	H14D—C14'—H14E	109.00
H14A—C14—H14C	109.00	H14D—C14'—H14F	109.00
H14B—C14—H14C	110.00	H14E—C14'—H14F	109.00
C3—C14—H14B	109.00	C3'—C15'—H15D	109.00
C3—C14—H14C	109.00	C3'—C15'—H15E	109.00
C3—C15—H15A	109.00	C3'—C15'—H15F	109.00
H15A—C15—H15B	109.00	H15D—C15'—H15E	109.00
C3—C15—H15B	109.00	H15D—C15'—H15F	109.00
C3—C15—H15C	110.00	H15E—C15'—H15F	109.00
H15B—C15—H15C	109.00	C6'—C16'—H16D	109.00
H15A—C15—H15C	109.00	C6'—C16'—H16E	110.00
C6—C16—H16B	110.00	C6'—C16'—H16F	109.00
C6—C16—H16A	109.00	H16D—C16'—H16E	109.00
H16A—C16—H16C	109.00	H16D—C16'—H16F	109.00
C6—C16—H16C	109.00	H16E—C16'—H16F	110.00
H16A—C16—H16B	109.00	C6'—C17'—H17D	109.00
H16B—C16—H16C	110.00	C6'—C17'—H17E	109.00
C6—C17—H17C	109.00	C6'—C17'—H17F	110.00
H17A—C17—H17B	109.00	H17D—C17'—H17E	109.00
C6—C17—H17B	109.00	H17D—C17'—H17F	109.00
H17B—C17—H17C	109.00	H17E—C17'—H17F	109.00
H17A—C17—H17C	110.00	C18'—C19'—H19'	121.00
C6—C17—H17A	110.00	C20'—C19'—H19'	121.00
C18—C19—H19	121.00	C19'—C20'—H20'	120.00
C20—C19—H19	121.00	C21'—C20'—H20'	120.00
C21—C20—H20	120.00	C20'—C21'—H21'	121.00
C19—C20—H20	120.00	C22'—C21'—H21'	121.00
C20—C21—H21	121.00	N1'—C22'—H22'	118.00
C22—C21—H21	121.00	C21'—C22'—H22'	118.00
C12—O1—C11—C4	175.0 (3)	O1—C12—C13—C8	−176.3 (3)
C12—O1—C11—C10	−4.7 (4)	O1—C12—C13—C9	5.9 (5)
C11—O1—C12—C5	−176.2 (3)	N1—C18—C19—C20	1.9 (6)
C11—O1—C12—C13	3.8 (4)	C9—C18—C19—C20	−176.5 (4)
C12'—O1'—C11'—C4'	175.5 (3)	C18—C19—C20—C21	−1.6 (7)
C12'—O1'—C11'—C10'	−4.8 (5)	C19—C20—C21—C22	−0.4 (7)
C11'—O1'—C12'—C5'	−174.0 (3)	C20—C21—C22—N1	2.4 (7)
C11'—O1'—C12'—C13'	6.2 (5)	C10'—C1'—C2'—C3'	26.7 (5)
C22—N1—C18—C19	−0.1 (6)	C2'—C1'—C10'—C9'	−173.5 (3)
C22—N1—C18—C9	178.4 (3)	C2'—C1'—C10'—C11'	2.5 (5)
C18—N1—C22—C21	−2.1 (6)	O3'—C1'—C2'—C3'	−155.7 (4)
C22'—N1'—C18'—C9'	−176.9 (4)	O3'—C1'—C10'—C9'	8.9 (6)
C22'—N1'—C18'—C19'	0.8 (6)	O3'—C1'—C10'—C11'	−175.1 (4)
C18'—N1'—C22'—C21'	2.0 (7)	C1'—C2'—C3'—C4'	−51.1 (4)
O3—C1—C2—C3	−156.9 (3)	C1'—C2'—C3'—C14'	67.9 (4)
C2—C1—C10—C9	−178.4 (3)	C1'—C2'—C3'—C15'	−170.5 (3)
C2—C1—C10—C11	1.4 (5)	C15'—C3'—C4'—C11'	168.1 (3)
C10—C1—C2—C3	26.7 (4)	C14'—C3'—C4'—C11'	−70.9 (4)
O3—C1—C10—C9	5.2 (5)	C2'—C3'—C4'—C11'	49.0 (4)
O3—C1—C10—C11	−175.0 (3)	C3'—C4'—C11'—C10'	−24.3 (5)
C1—C2—C3—C14	70.0 (4)	C3'—C4'—C11'—O1'	155.4 (3)
C1—C2—C3—C15	−169.6 (3)	C12'—C5'—C6'—C17'	−168.3 (3)
C1—C2—C3—C4	−50.6 (4)	C12'—C5'—C6'—C7'	−49.2 (4)
C15—C3—C4—C11	167.6 (3)	C6'—C5'—C12'—C13'	22.9 (5)
C14—C3—C4—C11	−72.7 (4)	C6'—C5'—C12'—O1'	−157.0 (3)
C2—C3—C4—C11	47.6 (4)	C12'—C5'—C6'—C16'	71.8 (4)
C3—C4—C11—O1	157.6 (3)	C16'—C6'—C7'—C8'	−67.8 (4)
C3—C4—C11—C10	−22.7 (5)	C17'—C6'—C7'—C8'	171.7 (3)
C12—C5—C6—C7	−48.9 (4)	C5'—C6'—C7'—C8'	53.0 (4)
C12—C5—C6—C17	70.9 (4)	C6'—C7'—C8'—O2'	154.9 (3)
C6—C5—C12—C13	24.7 (5)	C6'—C7'—C8'—C13'	−28.4 (4)
C6—C5—C12—O1	−155.3 (3)	O2'—C8'—C13'—C12'	175.2 (3)
C12—C5—C6—C16	−168.7 (3)	C7'—C8'—C13'—C12'	−1.6 (5)
C16—C6—C7—C8	169.7 (3)	C7'—C8'—C13'—C9'	178.0 (3)
C17—C6—C7—C8	−68.8 (4)	O2'—C8'—C13'—C9'	−5.3 (5)
C5—C6—C7—C8	49.9 (4)	C13'—C9'—C10'—C11'	15.9 (5)
C6—C7—C8—C13	−24.6 (5)	C10'—C9'—C13'—C8'	166.0 (3)
C6—C7—C8—O2	157.3 (4)	C18'—C9'—C10'—C1'	69.0 (4)
C7—C8—C13—C12	−4.2 (5)	C13'—C9'—C10'—C1'	−168.3 (3)
C7—C8—C13—C9	173.8 (3)	C18'—C9'—C13'—C12'	107.2 (4)
O2—C8—C13—C12	173.9 (3)	C10'—C9'—C18'—N1'	63.3 (4)
O2—C8—C13—C9	−8.2 (5)	C18'—C9'—C10'—C11'	−106.8 (4)
C13—C9—C10—C11	12.0 (4)	C13'—C9'—C18'—N1'	−57.9 (4)
C10—C9—C13—C8	169.2 (3)	C13'—C9'—C18'—C19'	124.4 (4)
C13—C9—C18—C19	117.6 (4)	C10'—C9'—C18'—C19'	−114.4 (4)
C13—C9—C18—N1	−60.8 (4)	C10'—C9'—C13'—C12'	−14.5 (4)
C18—C9—C13—C12	109.2 (4)	C18'—C9'—C13'—C8'	−72.3 (4)
C10—C9—C18—N1	59.9 (4)	C9'—C10'—C11'—C4'	172.4 (3)
C13—C9—C10—C1	−168.2 (3)	C1'—C10'—C11'—C4'	−3.5 (6)
C18—C9—C10—C1	71.0 (4)	C9'—C10'—C11'—O1'	−7.3 (6)
C18—C9—C10—C11	−108.8 (3)	C1'—C10'—C11'—O1'	176.8 (3)
C10—C9—C13—C12	−12.9 (4)	O1'—C12'—C13'—C8'	−175.9 (3)
C18—C9—C13—C8	−68.7 (4)	C5'—C12'—C13'—C9'	−175.3 (3)
C10—C9—C18—C19	−121.6 (4)	O1'—C12'—C13'—C9'	4.6 (5)
C9—C10—C11—O1	−4.1 (5)	C5'—C12'—C13'—C8'	4.3 (5)
C1—C10—C11—C4	−3.5 (5)	N1'—C18'—C19'—C20'	−2.2 (6)
C9—C10—C11—C4	176.3 (3)	C9'—C18'—C19'—C20'	175.3 (4)
C1—C10—C11—O1	176.1 (3)	C18'—C19'—C20'—C21'	0.9 (7)
C5—C12—C13—C9	−174.1 (3)	C19'—C20'—C21'—C22'	1.7 (7)
C5—C12—C13—C8	3.8 (5)	C20'—C21'—C22'—N1'	−3.3 (7)

Symmetry codes: (i) −x+2, −y, −z; (ii) −x+1, −y, −z+1; (iii) −x+3, −y, −z; (iv) x+1, y, z; (v) x−1, y+1, z; (vi) −x+2, −y, −z+1; (vii) −x+2, −y+1, −z; (viii) −x+1, −y+1, −z+1; (ix) x+1, y−1, z; (x) x−1, y, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2′	0.9700	2.5000	3.395 (5)	154.00