(1R*,2R*)-2-(Methyl­phenyl­amino)-1,2-di­hydro­naphthalen-1-ol–water (4/1)

The asymmetric unit of the title compound, 4C₁₇H₁₇NO·H₂O, contains four independent naphthalenol mol­ecules and one mol­ecule of water. All of the mol­ecules in the asymmetric unit are connected into a contiguous row via O—H...O hydrogen bonds. This unique hydrogen-bonded row is, in turn, linked to form extended O—H...O hydrogen-bonded chains, through unit-cell translations in the a direction. The hydrogen-bonding motif also contains an O(water)—H...π(arene) weak hydrogen bond, with an H...Cg distance of 2.64 (4) Å (where Cg is the center of gravity of the phenyl ring).

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.037
• wR factor = 0.090
• Data-to-parameter ratio = 7.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



PLAT_420  Alert B D-H Without Acceptor       O1W    -   H2W               ?

Author response: The hydogen-bonding motif also contains an O1W-H2W...\p(arene) weak hydrogen bond.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           26.02
         From the CIF: _reflns_number_total               5415
         Count of symmetry unique reflns         5422
         Completeness (_total/calc)             99.87%
         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
          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.


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 0 Alert Level C = Please check

---

S1. Comment

Recently, we reported a new rhodium-catalyzed ring-opening reaction of 1,4-dihydro-1,4-epoxynaphthalene with a wide range of nucleophiles (Lautens et al., 2000). The 1,2-regiochemistry and the trans relative stereochemistry of the title compound, (I), were established by our X-ray diffraction analysis when N-methylaniline is used as the nucleophile.

In (I), the four independent molecules (Figs. 1–4) and the water molecule are linked into a contiguous row through O—H···O hydrogen bonds (see Table 2 and Fig. 5). This hydrogen-bonded unit is, in turn, linked into extended O—H···O hydrogen-bonded chains through unit-cell translations in the a direction. The binary level graph set for this hydrogen-bonding motif is C⁵₅(10) (Bernstein et al.,1995). Only one of the H-atom donors from the water molecule is invloved in the above hydrogen-bonding motif. The other water H atom is involved in a weak O(water)—H···π(arene) bond [O1W···Cg = 3.384 (3) Å, H2W···Cg = 2.64 (4) Å and O1W—H2W···Cg = 148 (3)°, where Cg is the center of gravity of the phenyl ring containing atoms C5A/C6A/C7A/C8A/C9A/C10A]. The values for the O(water)—H ···π(arene) bond in (I) compare well with the mean values cited for other O—H..π(arene) bonds (Desiraju & Steiner, 1999).

The bond lengths and angles in the four molecules of (I) (A, B, C and D) are the same within experimental error, although there appears to be some differences with respect to the degree of rotation about the C11—N1 and N1—C2 bonds (see Table 1 for relevant torsion angles). In the dihydronaphthalene group, an analysis (Cremer & Pople, 1975) of the puckering in the six-membered ring (C1/C2/C3/C4/C5/C10) gives Q_T = 0.440 (3), 0.487 (3), 0.453 (3) and 0.411 (3) Å for molecules A, B, C and D, respectively. In all molecules, the conformation analysis of that ring (Duax et al., 1976) shows that the conformation is a half-chair, with a local pseudo-twofold axis running through the midpoints of the C1—C2 and C4—C5 bonds.

S2. Experimental

The title compound was obtained as a colourless oil in 95% yield by treatment of 1,4-dihydro-1,4-epoxynaphthalene with N-methylaniline and catalytic [Rh(cyclooctadiene)Cl]₂ and bis-(diphenylphosphino)ferrocene in refluxing tetrahydrofuran. The oil was allowed to stand at room temperature for several weeks during which time suitable crystals of (I) gradually formed.

S3. Refinement

All H atoms were included in calculated positions, with C—H distances of 0.95 (for sp²), 1.00 (for sp³), 0.98 (for methyl sp³) and 0.84 Å for O—H. They were then included in the refinement in riding-motion approximation, with U_iso = 1.2U_eq (U_iso = 1.5U_eq for methyl) of the carrier atom. The H atoms of the water molecule were located in a difference Fourier map and refined with tight geometric constraints (O—H = 0.8400± 0.0001 Å). Due to the lack of anomalous scatterers, the absolute configuration was not determined from the X-ray diffraction data and Friedel pairs were merged. The enantiomer has been assigned by reference to analogous reactions with an unchanging chiral ligand in the synthetic procedure.

Computing details

Data collection: COLLECT (Nonius BV, 1997-2002); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. View of molecule A of (I), showing the crystallographic labelling scheme. Ellipsoids are at the 30% probability level.
	Fig. 2. View of molecule B of (I), showing the crystallographic labelling scheme. Ellipsoids are at the 30% probability level.
	Fig. 3. View of molecule C of (I), showing the crystallographic labelling scheme. Ellipsoids are at the 30% probability level.
	Fig. 4. View of molecule D of (I), showing the crystallographic labelling scheme. Ellipsoids are at the 30% probability level.
	Fig. 5. View of the asymmtric unit and the hydrogen-bonding mode (shown with dashed lines), which connects the four title moleclues and the water moleclue. A symmetry-related molcule of water is included [symmetry code: (i) 1 + x, y, z] to indicate the extended hydrogen-bond motif.

(1R*,2R*)-2-(Methylphenylamino)-1,2-dihydronaphthalen-1-ol–water (4/1)

Crystal data

4C17H17NO·H2O	Dx = 1.237 Mg m^−3
Mr = 1023.28	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P31	Cell parameters from 49468 reflections
Hall symbol: P 31	θ = 2.6–26.1°
a = 12.3595 (1) Å	µ = 0.08 mm^−1
c = 31.1411 (4) Å	T = 150 K
V = 4119.71 (7) Å^3	Block, colourless
Z = 3	0.25 × 0.24 × 0.20 mm
F(000) = 1638

Data collection

Nonius KappaCCD diffractometer	4878 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 26.0°, θmin = 2.7°
Detector resolution: 9 pixels mm^-1	h = −15→15
ϕ scans and ω scans with κ offsets	k = −12→15
49468 measured reflections	l = −38→38
5415 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0489P)^2 + 0.6948P] where P = (Fo^2 + 2Fc^2)/3
5415 reflections	(Δ/σ)max = 0.001
708 parameters	Δρmax = 0.19 e Å^−3
3 restraints	Δρmin = −0.22 e Å^−3

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
O1A	0.13698 (19)	−0.00221 (19)	0.37733 (6)	0.0444 (5)
H1OA	0.2070	0.0074	0.3705	0.053*
N1A	0.2851 (2)	0.1307 (2)	0.45318 (7)	0.0385 (5)
C1A	0.1043 (2)	−0.0548 (2)	0.41909 (8)	0.0355 (6)
H1AB	0.1450	−0.1060	0.4245	0.043*
C2A	0.1484 (2)	0.0477 (2)	0.45274 (8)	0.0358 (6)
H2AA	0.1128	0.1014	0.4440	0.043*
C3A	0.0927 (3)	−0.0048 (3)	0.49634 (8)	0.0384 (6)
H3AA	0.1399	0.0322	0.5216	0.046*
C4A	−0.0221 (3)	−0.1025 (3)	0.49933 (9)	0.0386 (6)
H4AA	−0.0557	−0.1344	0.5269	0.046*
C5A	−0.0980 (3)	−0.1624 (2)	0.46123 (8)	0.0343 (6)
C6A	−0.2262 (3)	−0.2421 (2)	0.46269 (9)	0.0386 (6)
H6AA	−0.2683	−0.2595	0.4895	0.046*
C7A	−0.2936 (3)	−0.2964 (3)	0.42596 (10)	0.0449 (7)
H7AA	−0.3817	−0.3490	0.4274	0.054*
C8A	−0.2332 (3)	−0.2744 (3)	0.38714 (10)	0.0482 (7)
H8AA	−0.2798	−0.3128	0.3619	0.058*
C9A	−0.1052 (3)	−0.1966 (3)	0.38464 (9)	0.0440 (7)
H9AA	−0.0643	−0.1829	0.3577	0.053*
C10A	−0.0356 (2)	−0.1383 (2)	0.42122 (8)	0.0346 (6)
C11A	0.3319 (2)	0.2581 (2)	0.46307 (8)	0.0352 (6)
C12A	0.2683 (3)	0.3205 (3)	0.45095 (10)	0.0440 (7)
H12A	0.1934	0.2772	0.4348	0.053*
C13A	0.3125 (3)	0.4431 (3)	0.46203 (11)	0.0516 (8)
H13A	0.2661	0.4823	0.4541	0.062*
C14A	0.4226 (3)	0.5103 (3)	0.48435 (11)	0.0554 (8)
H14A	0.4515	0.5945	0.4924	0.067*
C15A	0.4900 (3)	0.4526 (3)	0.49472 (10)	0.0523 (8)
H15A	0.5678	0.4986	0.5091	0.063*
C16A	0.4456 (3)	0.3283 (3)	0.48442 (9)	0.0439 (7)
H16A	0.4933	0.2902	0.4920	0.053*
C17A	0.3563 (3)	0.0740 (3)	0.46843 (11)	0.0495 (7)
H17A	0.4418	0.1209	0.4573	0.074*
H17B	0.3168	−0.0126	0.4584	0.074*
H17C	0.3583	0.0756	0.4999	0.074*
O1B	−0.39625 (19)	0.17881 (19)	0.34990 (6)	0.0438 (5)
H1OB	−0.3566	0.1400	0.3487	0.053*
N1B	−0.35436 (18)	0.10527 (19)	0.26670 (8)	0.0366 (5)
C1B	−0.3642 (2)	0.2603 (2)	0.31394 (8)	0.0316 (5)
H1BB	−0.2714	0.3159	0.3132	0.038*
C2B	−0.4061 (2)	0.1873 (2)	0.27192 (8)	0.0297 (5)
H2BA	−0.4990	0.1327	0.2736	0.036*
C3B	−0.3795 (2)	0.2763 (3)	0.23495 (8)	0.0375 (6)
H3BA	−0.3539	0.2606	0.2080	0.045*
C4B	−0.3915 (2)	0.3752 (3)	0.23993 (9)	0.0385 (6)
H4BA	−0.3743	0.4307	0.2165	0.046*
C5B	−0.4314 (2)	0.4012 (2)	0.28121 (8)	0.0329 (5)
C6B	−0.4824 (3)	0.4793 (2)	0.28404 (10)	0.0437 (7)
H6BA	−0.4863	0.5218	0.2592	0.052*
C7B	−0.5276 (3)	0.4955 (3)	0.32281 (12)	0.0509 (8)
H7BA	−0.5627	0.5484	0.3244	0.061*
C8B	−0.5214 (3)	0.4346 (3)	0.35905 (11)	0.0487 (7)
H8BA	−0.5531	0.4450	0.3856	0.058*
C9B	−0.4689 (3)	0.3581 (2)	0.35679 (9)	0.0398 (6)
H9BA	−0.4639	0.3173	0.3819	0.048*
C10B	−0.4244 (2)	0.3408 (2)	0.31855 (8)	0.0311 (5)
C11B	−0.4283 (2)	−0.0205 (2)	0.25704 (8)	0.0319 (5)
C12B	−0.5585 (2)	−0.0845 (2)	0.26197 (10)	0.0418 (6)
H12B	−0.5987	−0.0408	0.2720	0.050*
C13B	−0.6289 (3)	−0.2097 (3)	0.25257 (11)	0.0523 (8)
H13B	−0.7170	−0.2506	0.2562	0.063*
C14B	−0.5754 (3)	−0.2776 (3)	0.23803 (11)	0.0548 (8)
H14B	−0.6251	−0.3640	0.2317	0.066*
C15B	−0.4484 (3)	−0.2164 (3)	0.23307 (10)	0.0495 (7)
H15B	−0.4098	−0.2613	0.2228	0.059*
C16B	−0.3747 (3)	−0.0904 (3)	0.24260 (9)	0.0392 (6)
H16B	−0.2866	−0.0511	0.2393	0.047*
C17B	−0.2215 (3)	0.1660 (3)	0.25810 (12)	0.0502 (8)
H17D	−0.1838	0.1283	0.2760	0.075*
H17E	−0.1827	0.2552	0.2647	0.075*
H17F	−0.2080	0.1554	0.2277	0.075*
O1C	−0.26497 (19)	0.04666 (18)	0.36884 (6)	0.0405 (4)
H1OC	−0.1865	0.0871	0.3694	0.049*
N1C	−0.16897 (19)	0.18273 (19)	0.44974 (7)	0.0320 (4)
C1C	−0.3112 (2)	−0.0104 (2)	0.40969 (8)	0.0327 (5)
H1CB	−0.2618	−0.0496	0.4196	0.039*
C2C	−0.2990 (2)	0.0862 (2)	0.44294 (8)	0.0289 (5)
H2CA	−0.3428	0.1289	0.4309	0.035*
C3C	−0.3653 (2)	0.0240 (2)	0.48399 (8)	0.0361 (6)
H3CA	−0.3314	0.0634	0.5108	0.043*
C4C	−0.4698 (3)	−0.0846 (3)	0.48315 (9)	0.0419 (6)
H4CA	−0.5114	−0.1220	0.5093	0.050*
C5C	−0.5224 (3)	−0.1483 (2)	0.44242 (9)	0.0400 (6)
C6C	−0.6476 (3)	−0.2433 (3)	0.43987 (12)	0.0538 (8)
H6CA	−0.6984	−0.2683	0.4649	0.065*
C7C	−0.6973 (3)	−0.3006 (3)	0.40108 (14)	0.0624 (10)
H7CA	−0.7825	−0.3642	0.3994	0.075*
C8C	−0.6237 (3)	−0.2658 (3)	0.36491 (13)	0.0589 (9)
H8CA	−0.6585	−0.3062	0.3384	0.071*
C9C	−0.4977 (3)	−0.1713 (3)	0.36674 (10)	0.0480 (7)
H9CA	−0.4473	−0.1487	0.3417	0.058*
C10C	−0.4474 (3)	−0.1114 (2)	0.40520 (9)	0.0370 (6)
C11C	−0.1408 (2)	0.3057 (2)	0.45853 (8)	0.0308 (5)
C12C	−0.2189 (3)	0.3517 (2)	0.44568 (9)	0.0378 (6)
H12C	−0.2964	0.2972	0.4321	0.045*
C13C	−0.1845 (3)	0.4760 (3)	0.45249 (10)	0.0459 (7)
H13C	−0.2389	0.5053	0.4436	0.055*
C14C	−0.0723 (3)	0.5577 (3)	0.47203 (10)	0.0463 (7)
H14C	−0.0490	0.6427	0.4763	0.056*
C15C	0.0049 (3)	0.5137 (3)	0.48512 (9)	0.0436 (7)
H15C	0.0823	0.5690	0.4985	0.052*
C16C	−0.0288 (2)	0.3896 (2)	0.47901 (9)	0.0361 (6)
H16C	0.0252	0.3609	0.4889	0.043*
C17C	−0.0935 (3)	0.1392 (3)	0.47167 (10)	0.0422 (6)
H17G	−0.0056	0.1922	0.4636	0.063*
H17H	−0.1219	0.0526	0.4633	0.063*
H17I	−0.1024	0.1435	0.5028	0.063*
O1D	0.02106 (18)	0.13985 (17)	0.35565 (6)	0.0389 (4)
H1OD	0.0435	0.0862	0.3579	0.047*
N1D	0.12773 (18)	0.08079 (19)	0.28108 (7)	0.0326 (5)
C1D	0.0976 (2)	0.2314 (2)	0.32460 (8)	0.0301 (5)
H1DB	0.1869	0.2691	0.3337	0.036*
C2D	0.0826 (2)	0.1697 (2)	0.28051 (8)	0.0285 (5)
H2DA	−0.0091	0.1207	0.2744	0.034*
C3D	0.1405 (2)	0.2661 (2)	0.24550 (8)	0.0347 (6)
H3DA	0.1765	0.2492	0.2213	0.042*
C4D	0.1421 (2)	0.3737 (2)	0.24791 (8)	0.0365 (6)
H4DA	0.1769	0.4316	0.2249	0.044*
C5D	0.0914 (2)	0.4054 (2)	0.28525 (8)	0.0311 (5)
C6D	0.0654 (3)	0.5027 (2)	0.28385 (9)	0.0388 (6)
H6DA	0.0832	0.5514	0.2585	0.047*
C7D	0.0138 (3)	0.5294 (2)	0.31905 (10)	0.0421 (6)
H7DA	−0.0039	0.5958	0.3178	0.051*
C8D	−0.0115 (3)	0.4588 (3)	0.35580 (9)	0.0410 (6)
H8DA	−0.0464	0.4772	0.3800	0.049*
C9D	0.0135 (2)	0.3613 (2)	0.35792 (8)	0.0348 (6)
H9DA	−0.0044	0.3134	0.3835	0.042*
C10D	0.0644 (2)	0.3335 (2)	0.32295 (8)	0.0291 (5)
C11D	0.0489 (2)	−0.0440 (2)	0.27010 (8)	0.0297 (5)
C12D	−0.0789 (2)	−0.1058 (2)	0.27971 (8)	0.0345 (5)
H12D	−0.1141	−0.0611	0.2929	0.041*
C13D	−0.1544 (3)	−0.2312 (3)	0.27027 (9)	0.0432 (7)
H13D	−0.2408	−0.2714	0.2771	0.052*
C14D	−0.1067 (3)	−0.2990 (3)	0.25108 (10)	0.0484 (7)
H14D	−0.1592	−0.3853	0.2450	0.058*
C15D	0.0191 (3)	−0.2390 (3)	0.24091 (10)	0.0484 (7)
H15D	0.0527	−0.2846	0.2273	0.058*
C16D	0.0969 (3)	−0.1136 (3)	0.25027 (9)	0.0389 (6)
H16D	0.1832	−0.0744	0.2433	0.047*
C17D	0.2622 (2)	0.1335 (3)	0.27839 (9)	0.0380 (6)
H17J	0.2857	0.0780	0.2930	0.057*
H17K	0.3041	0.2157	0.2922	0.057*
H17L	0.2873	0.1422	0.2482	0.057*
O1W	−0.64623 (19)	0.00001 (19)	0.36067 (9)	0.0626 (6)
H1W	−0.5739	0.062	0.3590	0.075*
H2W	−0.647	−0.0680	0.3625	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0424 (11)	0.0559 (12)	0.0363 (10)	0.0256 (10)	0.0058 (8)	0.0110 (9)
N1A	0.0367 (12)	0.0378 (12)	0.0479 (13)	0.0239 (10)	−0.0007 (10)	−0.0009 (10)
C1A	0.0399 (14)	0.0372 (14)	0.0334 (14)	0.0225 (12)	0.0015 (11)	0.0030 (11)
C2A	0.0322 (13)	0.0358 (14)	0.0428 (15)	0.0196 (12)	−0.0032 (11)	0.0006 (11)
C3A	0.0408 (15)	0.0410 (15)	0.0336 (14)	0.0205 (13)	−0.0052 (11)	−0.0019 (11)
C4A	0.0505 (16)	0.0403 (15)	0.0328 (14)	0.0284 (14)	0.0009 (12)	0.0034 (11)
C5A	0.0480 (15)	0.0251 (12)	0.0343 (14)	0.0216 (12)	−0.0001 (11)	0.0030 (10)
C6A	0.0409 (15)	0.0295 (13)	0.0463 (16)	0.0183 (12)	0.0060 (12)	0.0067 (11)
C7A	0.0443 (16)	0.0327 (14)	0.0519 (17)	0.0149 (12)	−0.0020 (13)	0.0042 (12)
C8A	0.0495 (17)	0.0430 (16)	0.0403 (16)	0.0142 (14)	−0.0074 (13)	−0.0017 (13)
C9A	0.0461 (16)	0.0457 (16)	0.0324 (14)	0.0171 (14)	−0.0029 (12)	0.0020 (12)
C10A	0.0403 (14)	0.0276 (12)	0.0377 (14)	0.0181 (11)	0.0028 (11)	0.0063 (10)
C11A	0.0351 (14)	0.0349 (14)	0.0358 (14)	0.0176 (12)	0.0085 (11)	0.0050 (11)
C12A	0.0340 (14)	0.0345 (15)	0.0610 (19)	0.0154 (12)	0.0064 (13)	0.0049 (13)
C13A	0.0415 (17)	0.0338 (15)	0.078 (2)	0.0178 (13)	0.0167 (15)	0.0116 (14)
C14A	0.0545 (19)	0.0295 (14)	0.069 (2)	0.0107 (14)	0.0173 (16)	0.0038 (14)
C15A	0.0424 (16)	0.0437 (17)	0.0515 (18)	0.0069 (14)	0.0052 (13)	0.0040 (14)
C16A	0.0356 (14)	0.0441 (16)	0.0473 (17)	0.0164 (13)	0.0044 (12)	0.0075 (13)
C17A	0.0486 (17)	0.0460 (17)	0.0645 (19)	0.0317 (14)	−0.0106 (14)	−0.0050 (14)
O1B	0.0575 (12)	0.0494 (12)	0.0373 (10)	0.0363 (10)	0.0023 (9)	0.0079 (8)
N1B	0.0236 (10)	0.0329 (11)	0.0559 (14)	0.0161 (9)	−0.0025 (9)	−0.0088 (10)
C1B	0.0300 (12)	0.0310 (12)	0.0337 (13)	0.0153 (11)	−0.0041 (10)	−0.0010 (10)
C2B	0.0217 (11)	0.0286 (12)	0.0395 (14)	0.0130 (10)	−0.0031 (10)	−0.0045 (10)
C3B	0.0361 (14)	0.0440 (15)	0.0325 (14)	0.0202 (12)	−0.0002 (11)	−0.0039 (11)
C4B	0.0356 (14)	0.0382 (14)	0.0381 (14)	0.0157 (12)	0.0033 (11)	0.0099 (11)
C5B	0.0240 (11)	0.0236 (12)	0.0432 (14)	0.0061 (10)	−0.0032 (10)	−0.0003 (10)
C6B	0.0375 (15)	0.0282 (13)	0.0645 (19)	0.0159 (12)	−0.0035 (13)	0.0038 (13)
C7B	0.0406 (16)	0.0321 (14)	0.084 (2)	0.0212 (13)	0.0028 (15)	−0.0091 (15)
C8B	0.0455 (17)	0.0413 (16)	0.0561 (19)	0.0193 (14)	0.0072 (14)	−0.0142 (14)
C9B	0.0401 (14)	0.0355 (14)	0.0399 (15)	0.0158 (12)	−0.0021 (12)	−0.0063 (11)
C10B	0.0268 (12)	0.0246 (12)	0.0380 (14)	0.0099 (10)	−0.0024 (10)	−0.0029 (10)
C11B	0.0337 (13)	0.0319 (13)	0.0330 (13)	0.0186 (11)	−0.0005 (10)	−0.0020 (10)
C12B	0.0330 (14)	0.0317 (14)	0.0604 (18)	0.0159 (12)	0.0040 (12)	−0.0062 (12)
C13B	0.0386 (15)	0.0351 (15)	0.074 (2)	0.0115 (13)	0.0066 (14)	−0.0086 (14)
C14B	0.0560 (19)	0.0285 (14)	0.073 (2)	0.0162 (14)	0.0041 (16)	−0.0093 (14)
C15B	0.0592 (19)	0.0415 (16)	0.0612 (19)	0.0351 (15)	0.0045 (15)	−0.0017 (14)
C16B	0.0391 (15)	0.0399 (15)	0.0459 (16)	0.0250 (13)	−0.0006 (12)	−0.0008 (12)
C17B	0.0253 (13)	0.0433 (16)	0.081 (2)	0.0162 (12)	−0.0035 (13)	−0.0166 (15)
O1C	0.0470 (11)	0.0452 (11)	0.0329 (9)	0.0257 (10)	0.0030 (8)	0.0032 (8)
N1C	0.0299 (11)	0.0285 (10)	0.0418 (12)	0.0178 (9)	−0.0017 (9)	−0.0011 (9)
C1C	0.0398 (14)	0.0339 (13)	0.0304 (13)	0.0229 (11)	0.0003 (11)	0.0034 (10)
C2C	0.0295 (12)	0.0283 (12)	0.0330 (13)	0.0175 (10)	−0.0019 (10)	0.0006 (10)
C3C	0.0376 (14)	0.0382 (14)	0.0336 (13)	0.0198 (12)	0.0002 (11)	−0.0007 (11)
C4C	0.0406 (15)	0.0434 (16)	0.0401 (15)	0.0197 (13)	0.0062 (12)	0.0089 (12)
C5C	0.0396 (15)	0.0278 (13)	0.0533 (17)	0.0172 (12)	−0.0018 (12)	0.0075 (11)
C6C	0.0431 (17)	0.0355 (15)	0.074 (2)	0.0129 (14)	−0.0031 (15)	0.0090 (15)
C7C	0.0481 (19)	0.0326 (16)	0.096 (3)	0.0121 (14)	−0.0215 (19)	0.0022 (17)
C8C	0.069 (2)	0.0379 (16)	0.072 (2)	0.0283 (16)	−0.0359 (19)	−0.0157 (16)
C9C	0.0609 (19)	0.0387 (15)	0.0504 (17)	0.0294 (15)	−0.0162 (14)	−0.0083 (13)
C10C	0.0432 (15)	0.0266 (12)	0.0470 (16)	0.0216 (11)	−0.0083 (12)	−0.0008 (11)
C11C	0.0373 (14)	0.0293 (12)	0.0286 (12)	0.0188 (11)	0.0055 (10)	0.0017 (10)
C12C	0.0443 (15)	0.0345 (14)	0.0416 (14)	0.0251 (12)	−0.0033 (12)	−0.0016 (11)
C13C	0.0609 (19)	0.0394 (16)	0.0488 (17)	0.0336 (15)	0.0057 (14)	0.0051 (13)
C14C	0.0603 (19)	0.0281 (14)	0.0498 (17)	0.0214 (14)	0.0107 (14)	0.0014 (12)
C15C	0.0457 (16)	0.0331 (14)	0.0436 (16)	0.0135 (13)	0.0069 (12)	−0.0034 (12)
C16C	0.0348 (14)	0.0337 (14)	0.0401 (14)	0.0173 (11)	0.0057 (11)	0.0008 (11)
C17C	0.0340 (14)	0.0357 (14)	0.0631 (18)	0.0222 (12)	−0.0091 (13)	−0.0049 (13)
O1D	0.0498 (11)	0.0362 (10)	0.0363 (10)	0.0258 (9)	0.0102 (8)	0.0090 (8)
N1D	0.0242 (10)	0.0302 (11)	0.0433 (12)	0.0137 (9)	−0.0034 (9)	−0.0056 (9)
C1D	0.0287 (12)	0.0294 (12)	0.0296 (12)	0.0126 (10)	0.0021 (10)	0.0043 (10)
C2D	0.0232 (11)	0.0288 (12)	0.0341 (13)	0.0135 (10)	−0.0005 (9)	0.0000 (10)
C3D	0.0341 (13)	0.0427 (15)	0.0276 (13)	0.0193 (12)	0.0027 (10)	−0.0004 (11)
C4D	0.0343 (13)	0.0364 (14)	0.0324 (13)	0.0129 (11)	0.0043 (11)	0.0057 (11)
C5D	0.0242 (12)	0.0259 (12)	0.0354 (13)	0.0066 (10)	−0.0009 (10)	0.0009 (10)
C6D	0.0398 (15)	0.0280 (13)	0.0444 (15)	0.0138 (12)	−0.0027 (12)	0.0047 (11)
C7D	0.0424 (15)	0.0277 (13)	0.0567 (17)	0.0178 (12)	−0.0038 (13)	−0.0036 (12)
C8D	0.0403 (15)	0.0365 (15)	0.0464 (16)	0.0194 (12)	0.0027 (12)	−0.0054 (12)
C9D	0.0384 (14)	0.0312 (13)	0.0305 (13)	0.0143 (11)	0.0017 (11)	−0.0013 (10)
C10D	0.0248 (11)	0.0235 (11)	0.0343 (13)	0.0086 (10)	−0.0039 (10)	−0.0030 (10)
C11D	0.0289 (12)	0.0286 (12)	0.0293 (12)	0.0126 (10)	−0.0054 (10)	0.0003 (10)
C12D	0.0336 (13)	0.0324 (13)	0.0325 (13)	0.0129 (11)	−0.0025 (10)	−0.0004 (10)
C13D	0.0404 (15)	0.0383 (15)	0.0344 (14)	0.0073 (13)	−0.0066 (12)	0.0049 (11)
C14D	0.061 (2)	0.0284 (14)	0.0497 (17)	0.0172 (14)	−0.0181 (14)	−0.0013 (12)
C15D	0.065 (2)	0.0374 (15)	0.0525 (17)	0.0331 (15)	−0.0188 (15)	−0.0086 (13)
C16D	0.0414 (15)	0.0396 (15)	0.0410 (15)	0.0243 (13)	−0.0096 (12)	−0.0044 (12)
C17D	0.0245 (13)	0.0409 (15)	0.0496 (16)	0.0170 (12)	−0.0019 (11)	−0.0052 (12)
O1W	0.0534 (13)	0.0579 (15)	0.0844 (16)	0.0338 (12)	0.0131 (13)	0.0104 (13)

Geometric parameters (Å, º)

O1A—C1A	1.419 (3)	O1C—H1OC	0.8400
O1A—H1OA	0.8400	N1C—C11C	1.405 (3)
N1A—C11A	1.413 (3)	N1C—C17C	1.458 (3)
N1A—C17A	1.452 (3)	N1C—C2C	1.461 (3)
N1A—C2A	1.474 (3)	C1C—C10C	1.520 (4)
C1A—C10A	1.508 (4)	C1C—C2C	1.530 (3)
C1A—C2A	1.520 (4)	C1C—H1CB	1.0000
C1A—H1AB	1.0000	C2C—C3C	1.506 (3)
C2A—C3A	1.514 (4)	C2C—H2CA	1.0000
C2A—H2AA	1.0000	C3C—C4C	1.318 (4)
C3A—C4A	1.330 (4)	C3C—H3CA	0.9500
C3A—H3AA	0.9500	C4C—C5C	1.462 (4)
C4A—C5A	1.463 (4)	C4C—H4CA	0.9500
C4A—H4AA	0.9500	C5C—C6C	1.402 (4)
C5A—C6A	1.387 (4)	C5C—C10C	1.410 (4)
C5A—C10A	1.416 (4)	C6C—C7C	1.379 (5)
C6A—C7A	1.376 (4)	C6C—H6CA	0.9500
C6A—H6AA	0.9500	C7C—C8C	1.374 (6)
C7A—C8A	1.374 (4)	C7C—H7CA	0.9500
C7A—H7AA	0.9500	C8C—C9C	1.405 (5)
C8A—C9A	1.384 (4)	C8C—H8CA	0.9500
C8A—H8AA	0.9500	C9C—C10C	1.381 (4)
C9A—C10A	1.392 (4)	C9C—H9CA	0.9500
C9A—H9AA	0.9500	C11C—C16C	1.401 (4)
C11A—C16A	1.396 (4)	C11C—C12C	1.402 (4)
C11A—C12A	1.400 (4)	C12C—C13C	1.390 (4)
C12A—C13A	1.374 (4)	C12C—H12C	0.9500
C12A—H12A	0.9500	C13C—C14C	1.383 (5)
C13A—C14A	1.377 (5)	C13C—H13C	0.9500
C13A—H13A	0.9500	C14C—C15C	1.376 (4)
C14A—C15A	1.378 (5)	C14C—H14C	0.9500
C14A—H14A	0.9500	C15C—C16C	1.387 (4)
C15A—C16A	1.386 (4)	C15C—H15C	0.9500
C15A—H15A	0.9500	C16C—H16C	0.9500
C16A—H16A	0.9500	C17C—H17G	0.9800
C17A—H17A	0.9800	C17C—H17H	0.9800
C17A—H17B	0.9800	C17C—H17I	0.9800
C17A—H17C	0.9800	O1D—C1D	1.428 (3)
O1B—C1B	1.423 (3)	O1D—H1OD	0.8400
O1B—H1OB	0.8400	N1D—C11D	1.394 (3)
N1B—C11B	1.386 (3)	N1D—C17D	1.452 (3)
N1B—C17B	1.449 (3)	N1D—C2D	1.461 (3)
N1B—C2B	1.454 (3)	C1D—C10D	1.511 (3)
C1B—C10B	1.518 (3)	C1D—C2D	1.536 (3)
C1B—C2B	1.525 (3)	C1D—H1DB	1.0000
C1B—H1BB	1.0000	C2D—C3D	1.505 (3)
C2B—C3B	1.510 (4)	C2D—H2DA	1.0000
C2B—H2BA	1.0000	C3D—C4D	1.322 (4)
C3B—C4B	1.313 (4)	C3D—H3DA	0.9500
C3B—H3BA	0.9500	C4D—C5D	1.464 (4)
C4B—C5B	1.468 (4)	C4D—H4DA	0.9500
C4B—H4BA	0.9500	C5D—C6D	1.393 (4)
C5B—C6B	1.396 (4)	C5D—C10D	1.408 (3)
C5B—C10B	1.408 (4)	C6D—C7D	1.388 (4)
C6B—C7B	1.386 (4)	C6D—H6DA	0.9500
C6B—H6BA	0.9500	C7D—C8D	1.376 (4)
C7B—C8B	1.379 (5)	C7D—H7DA	0.9500
C7B—H7BA	0.9500	C8D—C9D	1.387 (4)
C8B—C9B	1.391 (4)	C8D—H8DA	0.9500
C8B—H8BA	0.9500	C9D—C10D	1.385 (4)
C9B—C10B	1.373 (4)	C9D—H9DA	0.9500
C9B—H9BA	0.9500	C11D—C12D	1.400 (3)
C11B—C16B	1.401 (4)	C11D—C16D	1.409 (4)
C11B—C12B	1.403 (4)	C12D—C13D	1.383 (4)
C12B—C13B	1.375 (4)	C12D—H12D	0.9500
C12B—H12B	0.9500	C13D—C14D	1.378 (5)
C13B—C14B	1.379 (4)	C13D—H13D	0.9500
C13B—H13B	0.9500	C14D—C15D	1.384 (5)
C14B—C15B	1.368 (5)	C14D—H14D	0.9500
C14B—H14B	0.9500	C15D—C16D	1.386 (4)
C15B—C16B	1.386 (4)	C15D—H15D	0.9500
C15B—H15B	0.9500	C16D—H16D	0.9500
C16B—H16B	0.9500	C17D—H17J	0.9800
C17B—H17D	0.9800	C17D—H17K	0.9800
C17B—H17E	0.9800	C17D—H17L	0.9800
C17B—H17F	0.9800	O1W—H1W	0.8400
O1C—C1C	1.428 (3)	O1W—H2W	0.8400
C1A—O1A—H1OA	109.5	C11C—N1C—C17C	116.7 (2)
C11A—N1A—C17A	117.2 (2)	C11C—N1C—C2C	119.21 (19)
C11A—N1A—C2A	117.8 (2)	C17C—N1C—C2C	114.3 (2)
C17A—N1A—C2A	115.3 (2)	O1C—C1C—C10C	109.2 (2)
O1A—C1A—C10A	108.7 (2)	O1C—C1C—C2C	111.0 (2)
O1A—C1A—C2A	110.4 (2)	C10C—C1C—C2C	109.9 (2)
C10A—C1A—C2A	110.6 (2)	O1C—C1C—H1CB	108.9
O1A—C1A—H1AB	109.1	C10C—C1C—H1CB	108.9
C10A—C1A—H1AB	109.1	C2C—C1C—H1CB	108.9
C2A—C1A—H1AB	109.1	N1C—C2C—C3C	112.9 (2)
N1A—C2A—C3A	114.0 (2)	N1C—C2C—C1C	112.01 (19)
N1A—C2A—C1A	113.3 (2)	C3C—C2C—C1C	111.1 (2)
C3A—C2A—C1A	111.4 (2)	N1C—C2C—H2CA	106.8
N1A—C2A—H2AA	105.8	C3C—C2C—H2CA	106.8
C3A—C2A—H2AA	105.8	C1C—C2C—H2CA	106.8
C1A—C2A—H2AA	105.8	C4C—C3C—C2C	120.6 (2)
C4A—C3A—C2A	120.1 (2)	C4C—C3C—H3CA	119.7
C4A—C3A—H3AA	119.9	C2C—C3C—H3CA	119.7
C2A—C3A—H3AA	119.9	C3C—C4C—C5C	120.7 (2)
C3A—C4A—C5A	121.7 (2)	C3C—C4C—H4CA	119.6
C3A—C4A—H4AA	119.1	C5C—C4C—H4CA	119.6
C5A—C4A—H4AA	119.1	C6C—C5C—C10C	119.8 (3)
C6A—C5A—C10A	119.1 (2)	C6C—C5C—C4C	120.5 (3)
C6A—C5A—C4A	123.3 (2)	C10C—C5C—C4C	119.7 (2)
C10A—C5A—C4A	117.6 (2)	C7C—C6C—C5C	120.1 (3)
C7A—C6A—C5A	121.1 (3)	C7C—C6C—H6CA	120.0
C7A—C6A—H6AA	119.4	C5C—C6C—H6CA	120.0
C5A—C6A—H6AA	119.4	C8C—C7C—C6C	120.2 (3)
C8A—C7A—C6A	119.9 (3)	C8C—C7C—H7CA	119.9
C8A—C7A—H7AA	120.0	C6C—C7C—H7CA	119.9
C6A—C7A—H7AA	120.0	C7C—C8C—C9C	120.8 (3)
C7A—C8A—C9A	120.4 (3)	C7C—C8C—H8CA	119.6
C7A—C8A—H8AA	119.8	C9C—C8C—H8CA	119.6
C9A—C8A—H8AA	119.8	C10C—C9C—C8C	119.7 (3)
C8A—C9A—C10A	120.6 (3)	C10C—C9C—H9CA	120.1
C8A—C9A—H9AA	119.7	C8C—C9C—H9CA	120.1
C10A—C9A—H9AA	119.7	C9C—C10C—C5C	119.5 (3)
C9A—C10A—C5A	118.7 (2)	C9C—C10C—C1C	122.5 (3)
C9A—C10A—C1A	121.2 (2)	C5C—C10C—C1C	118.0 (2)
C5A—C10A—C1A	120.0 (2)	C16C—C11C—C12C	117.1 (2)
C16A—C11A—C12A	117.0 (3)	C16C—C11C—N1C	120.6 (2)
C16A—C11A—N1A	121.4 (2)	C12C—C11C—N1C	122.3 (2)
C12A—C11A—N1A	121.6 (2)	C13C—C12C—C11C	120.8 (3)
C13A—C12A—C11A	121.1 (3)	C13C—C12C—H12C	119.6
C13A—C12A—H12A	119.4	C11C—C12C—H12C	119.6
C11A—C12A—H12A	119.4	C14C—C13C—C12C	121.0 (3)
C12A—C13A—C14A	121.3 (3)	C14C—C13C—H13C	119.5
C12A—C13A—H13A	119.3	C12C—C13C—H13C	119.5
C14A—C13A—H13A	119.3	C15C—C14C—C13C	118.9 (3)
C13A—C14A—C15A	118.5 (3)	C15C—C14C—H14C	120.6
C13A—C14A—H14A	120.7	C13C—C14C—H14C	120.6
C15A—C14A—H14A	120.7	C14C—C15C—C16C	120.8 (3)
C14A—C15A—C16A	120.8 (3)	C14C—C15C—H15C	119.6
C14A—C15A—H15A	119.6	C16C—C15C—H15C	119.6
C16A—C15A—H15A	119.6	C15C—C16C—C11C	121.4 (3)
C15A—C16A—C11A	121.1 (3)	C15C—C16C—H16C	119.3
C15A—C16A—H16A	119.4	C11C—C16C—H16C	119.3
C11A—C16A—H16A	119.4	N1C—C17C—H17G	109.5
N1A—C17A—H17A	109.5	N1C—C17C—H17H	109.5
N1A—C17A—H17B	109.5	H17G—C17C—H17H	109.5
H17A—C17A—H17B	109.5	N1C—C17C—H17I	109.5
N1A—C17A—H17C	109.5	H17G—C17C—H17I	109.5
H17A—C17A—H17C	109.5	H17H—C17C—H17I	109.5
H17B—C17A—H17C	109.5	C1D—O1D—H1OD	109.5
C1B—O1B—H1OB	109.5	C11D—N1D—C17D	119.5 (2)
C11B—N1B—C17B	118.8 (2)	C11D—N1D—C2D	120.73 (19)
C11B—N1B—C2B	122.22 (19)	C17D—N1D—C2D	116.4 (2)
C17B—N1B—C2B	116.1 (2)	O1D—C1D—C10D	109.61 (19)
O1B—C1B—C10B	109.6 (2)	O1D—C1D—C2D	110.15 (19)
O1B—C1B—C2B	111.4 (2)	C10D—C1D—C2D	111.6 (2)
C10B—C1B—C2B	109.63 (19)	O1D—C1D—H1DB	108.5
O1B—C1B—H1BB	108.7	C10D—C1D—H1DB	108.5
C10B—C1B—H1BB	108.7	C2D—C1D—H1DB	108.5
C2B—C1B—H1BB	108.7	N1D—C2D—C3D	113.2 (2)
N1B—C2B—C3B	114.2 (2)	N1D—C2D—C1D	111.43 (19)
N1B—C2B—C1B	111.8 (2)	C3D—C2D—C1D	111.3 (2)
C3B—C2B—C1B	109.7 (2)	N1D—C2D—H2DA	106.8
N1B—C2B—H2BA	106.9	C3D—C2D—H2DA	106.8
C3B—C2B—H2BA	106.9	C1D—C2D—H2DA	106.8
C1B—C2B—H2BA	106.9	C4D—C3D—C2D	121.1 (2)
C4B—C3B—C2B	120.2 (2)	C4D—C3D—H3DA	119.5
C4B—C3B—H3BA	119.9	C2D—C3D—H3DA	119.5
C2B—C3B—H3BA	119.9	C3D—C4D—C5D	121.4 (2)
C3B—C4B—C5B	120.9 (2)	C3D—C4D—H4DA	119.3
C3B—C4B—H4BA	119.5	C5D—C4D—H4DA	119.3
C5B—C4B—H4BA	119.5	C6D—C5D—C10D	119.1 (2)
C6B—C5B—C10B	118.9 (3)	C6D—C5D—C4D	121.4 (2)
C6B—C5B—C4B	121.6 (2)	C10D—C5D—C4D	119.5 (2)
C10B—C5B—C4B	119.4 (2)	C7D—C6D—C5D	120.8 (2)
C7B—C6B—C5B	120.6 (3)	C7D—C6D—H6DA	119.6
C7B—C6B—H6BA	119.7	C5D—C6D—H6DA	119.6
C5B—C6B—H6BA	119.7	C8D—C7D—C6D	119.5 (3)
C8B—C7B—C6B	119.9 (3)	C8D—C7D—H7DA	120.3
C8B—C7B—H7BA	120.0	C6D—C7D—H7DA	120.3
C6B—C7B—H7BA	120.0	C7D—C8D—C9D	120.7 (3)
C7B—C8B—C9B	120.1 (3)	C7D—C8D—H8DA	119.6
C7B—C8B—H8BA	120.0	C9D—C8D—H8DA	119.6
C9B—C8B—H8BA	120.0	C10D—C9D—C8D	120.3 (2)
C10B—C9B—C8B	120.6 (3)	C10D—C9D—H9DA	119.8
C10B—C9B—H9BA	119.7	C8D—C9D—H9DA	119.8
C8B—C9B—H9BA	119.7	C9D—C10D—C5D	119.5 (2)
C9B—C10B—C5B	119.9 (2)	C9D—C10D—C1D	121.9 (2)
C9B—C10B—C1B	123.4 (2)	C5D—C10D—C1D	118.5 (2)
C5B—C10B—C1B	116.7 (2)	N1D—C11D—C12D	121.7 (2)
N1B—C11B—C16B	120.8 (2)	N1D—C11D—C16D	120.5 (2)
N1B—C11B—C12B	122.4 (2)	C12D—C11D—C16D	117.7 (2)
C16B—C11B—C12B	116.8 (2)	C13D—C12D—C11D	120.7 (3)
C13B—C12B—C11B	120.9 (3)	C13D—C12D—H12D	119.6
C13B—C12B—H12B	119.5	C11D—C12D—H12D	119.6
C11B—C12B—H12B	119.5	C14D—C13D—C12D	121.3 (3)
C12B—C13B—C14B	121.9 (3)	C14D—C13D—H13D	119.4
C12B—C13B—H13B	119.1	C12D—C13D—H13D	119.4
C14B—C13B—H13B	119.1	C13D—C14D—C15D	118.8 (3)
C15B—C14B—C13B	117.9 (3)	C13D—C14D—H14D	120.6
C15B—C14B—H14B	121.1	C15D—C14D—H14D	120.6
C13B—C14B—H14B	121.1	C14D—C15D—C16D	121.0 (3)
C14B—C15B—C16B	121.7 (3)	C14D—C15D—H15D	119.5
C14B—C15B—H15B	119.2	C16D—C15D—H15D	119.5
C16B—C15B—H15B	119.2	C15D—C16D—C11D	120.4 (3)
C15B—C16B—C11B	120.9 (3)	C15D—C16D—H16D	119.8
C15B—C16B—H16B	119.6	C11D—C16D—H16D	119.8
C11B—C16B—H16B	119.6	N1D—C17D—H17J	109.5
N1B—C17B—H17D	109.5	N1D—C17D—H17K	109.5
N1B—C17B—H17E	109.5	H17J—C17D—H17K	109.5
H17D—C17B—H17E	109.5	N1D—C17D—H17L	109.5
N1B—C17B—H17F	109.5	H17J—C17D—H17L	109.5
H17D—C17B—H17F	109.5	H17K—C17D—H17L	109.5
H17E—C17B—H17F	109.5	H1W—O1W—H2W	113 (4)
C1C—O1C—H1OC	109.5
C11A—N1A—C2A—C3A	−85.5 (3)	C11C—N1C—C2C—C3C	−88.2 (3)
C17A—N1A—C2A—C3A	59.5 (3)	C17C—N1C—C2C—C3C	56.6 (3)
C11A—N1A—C2A—C1A	145.7 (2)	C11C—N1C—C2C—C1C	145.5 (2)
C17A—N1A—C2A—C1A	−69.3 (3)	C17C—N1C—C2C—C1C	−69.7 (3)
O1A—C1A—C2A—N1A	−61.3 (3)	O1C—C1C—C2C—N1C	−61.4 (3)
C10A—C1A—C2A—N1A	178.4 (2)	C10C—C1C—C2C—N1C	177.63 (19)
O1A—C1A—C2A—C3A	168.5 (2)	O1C—C1C—C2C—C3C	171.3 (2)
C10A—C1A—C2A—C3A	48.2 (3)	C10C—C1C—C2C—C3C	50.3 (3)
N1A—C2A—C3A—C4A	−163.8 (2)	N1C—C2C—C3C—C4C	−162.1 (2)
C1A—C2A—C3A—C4A	−34.0 (3)	C1C—C2C—C3C—C4C	−35.3 (3)
C2A—C3A—C4A—C5A	0.0 (4)	C2C—C3C—C4C—C5C	1.2 (4)
C3A—C4A—C5A—C6A	−163.2 (3)	C3C—C4C—C5C—C6C	−162.1 (3)
C3A—C4A—C5A—C10A	17.9 (4)	C3C—C4C—C5C—C10C	16.1 (4)
C10A—C5A—C6A—C7A	−0.9 (4)	C10C—C5C—C6C—C7C	0.1 (4)
C4A—C5A—C6A—C7A	−179.9 (3)	C4C—C5C—C6C—C7C	178.3 (3)
C5A—C6A—C7A—C8A	1.7 (4)	C5C—C6C—C7C—C8C	0.8 (5)
C6A—C7A—C8A—C9A	−0.8 (5)	C6C—C7C—C8C—C9C	−0.4 (5)
C7A—C8A—C9A—C10A	−0.8 (5)	C7C—C8C—C9C—C10C	−0.8 (4)
C8A—C9A—C10A—C5A	1.5 (4)	C8C—C9C—C10C—C5C	1.7 (4)
C8A—C9A—C10A—C1A	179.1 (3)	C8C—C9C—C10C—C1C	178.7 (3)
C6A—C5A—C10A—C9A	−0.6 (4)	C6C—C5C—C10C—C9C	−1.4 (4)
C4A—C5A—C10A—C9A	178.4 (2)	C4C—C5C—C10C—C9C	−179.6 (2)
C6A—C5A—C10A—C1A	−178.3 (2)	C6C—C5C—C10C—C1C	−178.4 (2)
C4A—C5A—C10A—C1A	0.7 (3)	C4C—C5C—C10C—C1C	3.3 (4)
O1A—C1A—C10A—C9A	27.5 (3)	O1C—C1C—C10C—C9C	24.9 (3)
C2A—C1A—C10A—C9A	148.9 (3)	C2C—C1C—C10C—C9C	146.9 (2)
O1A—C1A—C10A—C5A	−154.8 (2)	O1C—C1C—C10C—C5C	−158.1 (2)
C2A—C1A—C10A—C5A	−33.5 (3)	C2C—C1C—C10C—C5C	−36.1 (3)
C17A—N1A—C11A—C16A	3.6 (4)	C17C—N1C—C11C—C16C	14.4 (3)
C2A—N1A—C11A—C16A	148.0 (2)	C2C—N1C—C11C—C16C	158.4 (2)
C17A—N1A—C11A—C12A	−178.1 (3)	C17C—N1C—C11C—C12C	−168.7 (2)
C2A—N1A—C11A—C12A	−33.7 (4)	C2C—N1C—C11C—C12C	−24.7 (3)
C16A—C11A—C12A—C13A	−3.9 (4)	C16C—C11C—C12C—C13C	1.1 (4)
N1A—C11A—C12A—C13A	177.7 (3)	N1C—C11C—C12C—C13C	−175.9 (2)
C11A—C12A—C13A—C14A	1.9 (5)	C11C—C12C—C13C—C14C	0.1 (4)
C12A—C13A—C14A—C15A	1.4 (5)	C12C—C13C—C14C—C15C	−0.6 (4)
C13A—C14A—C15A—C16A	−2.5 (5)	C13C—C14C—C15C—C16C	−0.2 (4)
C14A—C15A—C16A—C11A	0.4 (5)	C14C—C15C—C16C—C11C	1.5 (4)
C12A—C11A—C16A—C15A	2.8 (4)	C12C—C11C—C16C—C15C	−1.9 (4)
N1A—C11A—C16A—C15A	−178.8 (3)	N1C—C11C—C16C—C15C	175.2 (2)
C11B—N1B—C2B—C3B	−106.1 (3)	C11D—N1D—C2D—C3D	−111.5 (2)
C17B—N1B—C2B—C3B	54.4 (3)	C17D—N1D—C2D—C3D	47.5 (3)
C11B—N1B—C2B—C1B	128.6 (2)	C11D—N1D—C2D—C1D	122.1 (2)
C17B—N1B—C2B—C1B	−70.9 (3)	C17D—N1D—C2D—C1D	−78.9 (3)
O1B—C1B—C2B—N1B	−56.5 (3)	O1D—C1D—C2D—N1D	−64.3 (2)
C10B—C1B—C2B—N1B	−178.0 (2)	C10D—C1D—C2D—N1D	173.72 (19)
O1B—C1B—C2B—C3B	175.69 (19)	O1D—C1D—C2D—C3D	168.29 (19)
C10B—C1B—C2B—C3B	54.2 (3)	C10D—C1D—C2D—C3D	46.3 (3)
N1B—C2B—C3B—C4B	−162.3 (2)	N1D—C2D—C3D—C4D	−158.7 (2)
C1B—C2B—C3B—C4B	−36.0 (3)	C1D—C2D—C3D—C4D	−32.3 (3)
C2B—C3B—C4B—C5B	−0.2 (4)	C2D—C3D—C4D—C5D	2.0 (4)
C3B—C4B—C5B—C6B	−159.3 (3)	C3D—C4D—C5D—C6D	−164.4 (3)
C3B—C4B—C5B—C10B	17.1 (4)	C3D—C4D—C5D—C10D	13.4 (4)
C10B—C5B—C6B—C7B	−1.1 (4)	C10D—C5D—C6D—C7D	0.2 (4)
C4B—C5B—C6B—C7B	175.4 (2)	C4D—C5D—C6D—C7D	178.0 (2)
C5B—C6B—C7B—C8B	0.4 (4)	C5D—C6D—C7D—C8D	0.2 (4)
C6B—C7B—C8B—C9B	0.6 (4)	C6D—C7D—C8D—C9D	−0.3 (4)
C7B—C8B—C9B—C10B	−0.9 (4)	C7D—C8D—C9D—C10D	0.0 (4)
C8B—C9B—C10B—C5B	0.2 (4)	C8D—C9D—C10D—C5D	0.4 (4)
C8B—C9B—C10B—C1B	179.0 (2)	C8D—C9D—C10D—C1D	177.5 (2)
C6B—C5B—C10B—C9B	0.8 (4)	C6D—C5D—C10D—C9D	−0.5 (3)
C4B—C5B—C10B—C9B	−175.7 (2)	C4D—C5D—C10D—C9D	−178.4 (2)
C6B—C5B—C10B—C1B	−178.1 (2)	C6D—C5D—C10D—C1D	−177.7 (2)
C4B—C5B—C10B—C1B	5.3 (3)	C4D—C5D—C10D—C1D	4.4 (3)
O1B—C1B—C10B—C9B	18.0 (3)	O1D—C1D—C10D—C9D	26.4 (3)
C2B—C1B—C10B—C9B	140.5 (2)	C2D—C1D—C10D—C9D	148.7 (2)
O1B—C1B—C10B—C5B	−163.1 (2)	O1D—C1D—C10D—C5D	−156.4 (2)
C2B—C1B—C10B—C5B	−40.6 (3)	C2D—C1D—C10D—C5D	−34.1 (3)
C17B—N1B—C11B—C16B	5.3 (4)	C17D—N1D—C11D—C12D	167.7 (2)
C2B—N1B—C11B—C16B	165.2 (2)	C2D—N1D—C11D—C12D	−34.0 (3)
C17B—N1B—C11B—C12B	−176.2 (3)	C17D—N1D—C11D—C16D	−9.9 (4)
C2B—N1B—C11B—C12B	−16.2 (4)	C2D—N1D—C11D—C16D	148.5 (2)
N1B—C11B—C12B—C13B	−179.2 (3)	N1D—C11D—C12D—C13D	−177.1 (2)
C16B—C11B—C12B—C13B	−0.6 (4)	C16D—C11D—C12D—C13D	0.5 (4)
C11B—C12B—C13B—C14B	0.1 (5)	C11D—C12D—C13D—C14D	−0.2 (4)
C12B—C13B—C14B—C15B	0.0 (5)	C12D—C13D—C14D—C15D	−0.6 (4)
C13B—C14B—C15B—C16B	0.6 (5)	C13D—C14D—C15D—C16D	0.9 (4)
C14B—C15B—C16B—C11B	−1.1 (5)	C14D—C15D—C16D—C11D	−0.6 (4)
N1B—C11B—C16B—C15B	179.8 (3)	N1D—C11D—C16D—C15D	177.5 (2)
C12B—C11B—C16B—C15B	1.1 (4)	C12D—C11D—C16D—C15D	−0.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1B—H1OB···O1C	0.84	2.08	2.881 (3)	160
O1C—H1OC···O1D	0.84	2.35	3.150 (3)	160
O1D—H1OD···O1A	0.84	2.04	2.847 (3)	161
O1A—H1OA···O1W^i	0.84	1.89	2.716 (3)	169
O1W—H1W···O1B	0.84	1.95	2.777 (3)	167

Symmetry code: (i) x+1, y, z.