rac-(Z)-2-(2-Thienylmethyl­ene)-1-aza­bicyclo­[2.2.2]octan-3-ol

The asymmetric unit of the racemic form of the title compound, C₁₂H₁₅NOS, contains four crystallographically independent mol­ecules. The olefinic bond connecting the 2-­thienyl and 1-aza­bicyclo­[2.2.2]octan-3-ol moieties has Z geometry. Strong hydrogen bonding occurs in a directed co-operative O—H...O—H...O—H...O—H R₄⁴(8) pattern that influences the conformation of the mol­ecules. Co-operative C—H...π inter­actions between thienyl rings are also present. The average dihedral angle between adjacent thienyl rings is 87.09 (4)°.

S1. Comment

Radiation therapy prevents cancer cells from growing and dividing, but can also damage normal cells. Radio-sensitizers are drugs that sensitize cancer cells to radiation therapy. Recent research in our laboratory has focused on the discovery of molecules that can either sensitize a tumour to radiation without affecting healthy tissue, or that can shield normal cells from radiation damage. Recently, we have reported (Sekhar et al., 2007) the radio-sensitizing activity of N-arylsubstituted rac-(Z)-2-(1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-ols. In addition to these indole analogues, we have also synthesized 1-azabicyclo[2.2.2]octan-3-ols linked to non-indolic systems, in order to compare their radio-sensitizing activities with those of the indole analogues. The title compound, (I), was prepared by the base-catalyzed reaction of thiophene-2-carboxaldehyde with 1-azabicyclo[2.2.2]octan-3-one and subsequent reduction to the corresponding secondary alcohol. In order to confirm the double-bond geometry, and to determine the molecular conformation in the crystal structure, the X-ray analysis of compound (I) has been carried out, and the results are presented here.

The asymmetric unit of (I) contains four crystallographically independent molecules, (IA)–(ID), with almost identical bond lengths and angles. The molecular structure and atom-numbering scheme of molecule (IA) are shown in Fig. 1, and selected bond lengths and angles are listed in Table 1.

The title molecule comprises a 1-azabicyclo[2.2.2]octan-3-ol moiety and a 2-thienyl group linked by a C5═C6 bond that has Z geometry. In this (Z) isomer, the C1—C5 bond is in the trans position with respect to the C6—C10 bond. The double bond has a nearly planar atomic arrangement, since the r.m.s. deviation from the best plane passing through atoms N1, C6, C10, C5 and C1 is 0.0061 (10) Å for (IA), 0.0972 (10) Å for (IB), 0.1943 (10) Å for (IC) and 0.2500 (10) Å for (ID). The geometries of the four molecules in the asymmetric unit are essentially the same, so only molecule A is discussed in detail here.

The bond angles around atoms C5A and C6A deviate from 120° and this is in general agreement with our earlier observation for a similar type of compound (Sonar et al., 2004). The angles N1A—C6A—C10A, C6A═C5A—C1A and C5A═C6A—C10A [114.02 (15), 126.55 (17) and 125.26 (17)°, respectively] are distorted as a consequence of the strain induced by the double-bond linkage at C5A═C6A. The azabicyclic system exhibits small distortions in geometry compared with standard tetrahedral values. The bond angles C6A—N1A—C7A, C10A—C9A—C11A and C9A—C11A—C12A [107.28 (14), 107.41 (15) and 107.79 (14)°, respectively] are, on average, smaller than the ideal tetrahedral value of 109.5°, while the bond angles N1A—C7A—C8A, O1A—C10A—C9A and N1A—C12A—C11A [111.32 (15), 113.84 (14) and 112.05 (14)°, respectively] are, on average, slightly larger than the tetrahedral value. The C4═C1—C5═C6 torsion angles [170.67 (19), 173.55 (19), 173.41 (19) and 170.85 (19)° for molecules A, B, C and D, respectively] indicate a deviation of the 2-thienyl ring from the plane of the double bond connected to the azabicyclic ring in these molecules. This small deviation facilitates a weak conjugation between the C5═C6 double bond and the 2-thienyl ring. This is also evident from the C1—C5 bond lengths [1.456 (3), 1.455 (3), 1.458 (3) and 1.451 (3) Å in molecules A, B, C and D, respectively].

Strong hydrogen bonds and weaker C—H···π interactions (Fig. 2) present in the crystal structure of (I) effectively group sets of four molecules together into roughly cylindrical units. Within each group, all molecules possess the same absolute configuration and are related to other groups of opposite hand via crystallographic inversion centres. The donor–acceptor direction of the R₄⁴(8) hydrogen-bonded motif comprising O1A—H1A···O1B—H1B···O1C—H1C···O1D—H1D···O1A (Table 2) is opposite from the directionality around the C—H···π linked thienyl rings (ringA—H4A···ringD—H4D···ringC—H4C···ringB—H4B···ringA). These C—H···π interactions, C4A···ringB, C4B···ringC, C4C···ringD and C4D···ringA with distances of 3.551 (2), 3.531 (2), 3.554 (2) and 3.565 (2) Å, respectively, effectively lock the thiophene rings into a single conformation. Dihedral angles between successive rings are A/B = 89.24 (4), B/C = 86.64 (4), C/D = 85.08 (4) and D/A = 87.39 (4)°.

S2. Experimental

The title compound was prepared according to the previously reported procedure of Sonar et al. (2004). Crystallization from ethyl acetate afforded yellow crystals [colourless given in experimental tables - which is correct?]. ¹H NMR (CDCl₃, δ, p.p.m.): 1.47–1.89 (m, 5H), 2.05 (s, 1H), 2.74–3.00 (m, 4H), 4.34 (s, 1H), 6.59 (s, 1H), 6.97 (d, 2H), 7.25 (d, 1H); ¹³C NMR (CDCl₃, δ, p.p.m.): 19.07, 25.37, 31.09, 46.64, 47.77, 70.61, 116.83, 125.47, 126.95, 127.49, 138.53, 149.20.

S3. Refinement

H atoms were found in a difference Fourier map and subsequently placed in idealized positions with constrained C—H distances of 0.95 Å (Csp²—H), 0.99 Å (CH₂) and 1.00 Å (CH) and with O—H = 0.84 Å. U_iso(H) values were set to either 1.2U_eq or 1.5_eq (OH only) of the parent atom.

Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1995); software used to prepare material for publication: SHELX97 and local procedures.

Figures

	Fig. 1. A view of molecule (IA), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The numbering schemes for molecules B, C and D are identical to the numbering scheme for molecule A.
	Fig. 2. A view of molecules (IA)–(ID). H atoms have been omitted for clarity, except for those involved in π interactions and H—O···H hydrogen bonds (dashed lines).

rac-(Z)-2-(2-Thienylmethylene)-1-azabicyclo[2.2.2]octan-3-ol

Crystal data

C12H15NOS	F(000) = 1888
Mr = 221.32	Dx = 1.338 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 19446 reflections
a = 14.7933 (3) Å	θ = 1.0–27.5°
b = 20.0349 (4) Å	µ = 0.27 mm^−1
c = 14.8243 (3) Å	T = 90 K
β = 90.2820 (7)°	Thin plate, colourless
V = 4393.61 (15) Å^3	0.38 × 0.35 × 0.03 mm
Z = 16

Data collection

Nonius KappaCCD area-detector diffractometer	10043 independent reflections
Radiation source: fine-focus sealed tube	7113 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
Detector resolution: 18 pixels mm^-1	θmax = 27.5°, θmin = 1.7°
ω scans at fixed χ = 55°	h = −19→19
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −25→25
Tmin = 0.906, Tmax = 0.992	l = −19→19
37339 measured 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0549P)^2 + 1.4384P] where P = (Fo^2 + 2Fc^2)/3
10043 reflections	(Δ/σ)max = 0.001
545 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.34 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 > 2σ(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
S1A	0.74404 (3)	0.14937 (2)	0.53118 (3)	0.02089 (12)
N1A	0.73352 (11)	0.29039 (8)	0.55614 (10)	0.0198 (3)
O1A	0.63637 (9)	0.38409 (7)	0.37043 (8)	0.0211 (3)
H1A	0.6859	0.3752	0.3457	0.032*
C1A	0.66001 (12)	0.17545 (9)	0.45713 (12)	0.0179 (4)
C2A	0.72215 (14)	0.06691 (9)	0.50794 (13)	0.0252 (4)
H2A	0.7545	0.0307	0.5340	0.030*
C3A	0.65327 (14)	0.05956 (10)	0.44797 (13)	0.0271 (5)
H3A	0.6313	0.0175	0.4281	0.033*
C4A	0.61785 (13)	0.12123 (9)	0.41829 (13)	0.0229 (4)
H4A	0.5698	0.1250	0.3758	0.027*
C5A	0.63713 (13)	0.24501 (9)	0.43981 (12)	0.0181 (4)
H5A	0.5959	0.2534	0.3918	0.022*
C6A	0.66827 (12)	0.29805 (9)	0.48452 (12)	0.0169 (4)
C7A	0.81976 (13)	0.31909 (9)	0.52400 (13)	0.0216 (4)
H7A1	0.8425	0.2922	0.4728	0.026*
H7A2	0.8653	0.3170	0.5731	0.026*
C8A	0.80757 (13)	0.39255 (9)	0.49348 (12)	0.0196 (4)
H8A1	0.8514	0.4215	0.5255	0.024*
H8A2	0.8186	0.3964	0.4279	0.024*
C9A	0.71054 (13)	0.41447 (9)	0.51522 (12)	0.0195 (4)
H9A	0.7014	0.4624	0.4987	0.023*
C10A	0.64266 (13)	0.37025 (9)	0.46493 (12)	0.0172 (4)
H10A	0.5817	0.3784	0.4917	0.021*
C11A	0.69522 (14)	0.40421 (9)	0.61635 (12)	0.0224 (4)
H11A	0.6346	0.4207	0.6334	0.027*
H11B	0.7411	0.4292	0.6516	0.027*
C12A	0.70305 (14)	0.32849 (9)	0.63614 (12)	0.0232 (4)
H12A	0.7465	0.3215	0.6863	0.028*
H12B	0.6435	0.3114	0.6556	0.028*
S1B	0.93186 (3)	0.13285 (2)	0.14966 (3)	0.02178 (12)
N1B	0.96319 (11)	0.27513 (8)	0.15764 (10)	0.0193 (3)
O1B	0.78363 (9)	0.37379 (7)	0.25620 (8)	0.0226 (3)
H1B	0.7609	0.3745	0.2042	0.034*
C1B	0.86176 (13)	0.16189 (9)	0.23453 (12)	0.0191 (4)
C2B	0.90240 (14)	0.05155 (10)	0.17130 (14)	0.0273 (5)
H2B	0.9251	0.0145	0.1385	0.033*
C3B	0.84319 (14)	0.04622 (10)	0.24033 (14)	0.0295 (5)
H3B	0.8202	0.0050	0.2619	0.035*
C4B	0.81938 (14)	0.10933 (10)	0.27672 (13)	0.0246 (4)
H4B	0.7784	0.1148	0.3253	0.029*
C5B	0.84853 (12)	0.23191 (9)	0.25679 (12)	0.0182 (4)
H5B	0.8027	0.2415	0.2996	0.022*
C6B	0.89334 (12)	0.28421 (9)	0.22398 (11)	0.0172 (4)
C7B	0.93158 (13)	0.30690 (9)	0.07280 (12)	0.0214 (4)
H7B1	0.8778	0.2828	0.0499	0.026*
H7B2	0.9796	0.3035	0.0268	0.026*
C8B	0.90717 (13)	0.38129 (9)	0.08751 (12)	0.0210 (4)
H8B1	0.9415	0.4096	0.0450	0.025*
H8B2	0.8418	0.3883	0.0763	0.025*
C9B	0.93096 (13)	0.40027 (9)	0.18530 (12)	0.0198 (4)
H9B	0.9179	0.4485	0.1964	0.024*
C10B	0.87748 (13)	0.35634 (9)	0.25050 (12)	0.0184 (4)
H10B	0.9044	0.3627	0.3119	0.022*
C11B	1.03170 (12)	0.38560 (9)	0.19972 (13)	0.0196 (4)
H11C	1.0507	0.3999	0.2609	0.024*
H11D	1.0682	0.4103	0.1549	0.024*
C12B	1.04625 (13)	0.30969 (9)	0.18858 (13)	0.0212 (4)
H12C	1.0951	0.3019	0.1444	0.025*
H12D	1.0658	0.2905	0.2471	0.025*
S1C	0.55607 (3)	0.15589 (2)	−0.04202 (3)	0.02126 (12)
N1C	0.56311 (10)	0.29615 (8)	−0.06757 (10)	0.0192 (3)
O1C	0.66761 (9)	0.39559 (7)	0.10825 (8)	0.0218 (3)
H1C	0.6170	0.3922	0.1333	0.033*
C1C	0.63776 (12)	0.18331 (9)	0.03381 (12)	0.0192 (4)
C2C	0.57733 (14)	0.07408 (10)	−0.01553 (13)	0.0263 (5)
H2C	0.5465	0.0374	−0.0423	0.032*
C3C	0.64337 (14)	0.06755 (10)	0.04811 (13)	0.0265 (5)
H3C	0.6640	0.0259	0.0707	0.032*
C4C	0.67774 (13)	0.13009 (10)	0.07684 (13)	0.0238 (4)
H4C	0.7238	0.1348	0.1213	0.029*
C5C	0.66225 (13)	0.25306 (9)	0.04761 (12)	0.0193 (4)
H5C	0.7048	0.2622	0.0942	0.023*
C6C	0.63075 (12)	0.30530 (9)	0.00118 (12)	0.0181 (4)
C7C	0.47919 (13)	0.32917 (9)	−0.03644 (13)	0.0221 (4)
H7C1	0.4567	0.3061	0.0180	0.027*
H7C2	0.4322	0.3255	−0.0840	0.027*
C8C	0.49557 (13)	0.40369 (9)	−0.01431 (13)	0.0213 (4)
H8C1	0.4532	0.4319	−0.0494	0.026*
H8C2	0.4852	0.4119	0.0507	0.026*
C9C	0.59352 (13)	0.42112 (9)	−0.03875 (12)	0.0203 (4)
H9C	0.6057	0.4694	−0.0268	0.024*
C10C	0.65939 (13)	0.37735 (9)	0.01526 (12)	0.0191 (4)
H10C	0.7204	0.3827	−0.0125	0.023*
C11C	0.60677 (14)	0.40524 (9)	−0.13907 (12)	0.0224 (4)
H11E	0.6682	0.4186	−0.1583	0.027*
H11F	0.5620	0.4299	−0.1761	0.027*
C12C	0.59377 (14)	0.32888 (9)	−0.15126 (12)	0.0217 (4)
H12E	0.5488	0.3208	−0.1997	0.026*
H12F	0.6517	0.3087	−0.1703	0.026*
S1D	0.36722 (3)	0.15446 (2)	0.34283 (3)	0.02194 (12)
N1D	0.34369 (11)	0.29662 (8)	0.33218 (10)	0.0214 (4)
O1D	0.51971 (9)	0.39123 (7)	0.22320 (8)	0.0220 (3)
H1D	0.5448	0.3871	0.2739	0.033*
C1D	0.43724 (13)	0.18024 (9)	0.25578 (12)	0.0194 (4)
C2D	0.38858 (14)	0.07187 (10)	0.32030 (13)	0.0264 (5)
H2D	0.3636	0.0359	0.3536	0.032*
C3D	0.44544 (14)	0.06396 (10)	0.24928 (13)	0.0258 (5)
H3D	0.4642	0.0218	0.2268	0.031*
C4D	0.47342 (14)	0.12584 (10)	0.21279 (13)	0.0231 (4)
H4D	0.5135	0.1294	0.1632	0.028*
C5D	0.45272 (13)	0.24932 (9)	0.23074 (12)	0.0184 (4)
H5D	0.4979	0.2571	0.1866	0.022*
C6D	0.41065 (12)	0.30306 (9)	0.26271 (12)	0.0180 (4)
C7D	0.37643 (14)	0.33301 (9)	0.41320 (12)	0.0234 (4)
H7D1	0.4309	0.3104	0.4374	0.028*
H7D2	0.3293	0.3317	0.4603	0.028*
C8D	0.39972 (13)	0.40673 (9)	0.39147 (12)	0.0218 (4)
H8D1	0.3663	0.4369	0.4323	0.026*
H8D2	0.4653	0.4146	0.4000	0.026*
C9D	0.37273 (13)	0.42054 (9)	0.29291 (12)	0.0203 (4)
H9D	0.3843	0.4683	0.2772	0.024*
C10D	0.42616 (12)	0.37421 (9)	0.23040 (12)	0.0181 (4)
H10D	0.3989	0.3781	0.1687	0.022*
C11D	0.27217 (13)	0.40402 (10)	0.28181 (13)	0.0238 (4)
H11G	0.2518	0.4151	0.2199	0.029*
H11H	0.2360	0.4305	0.3249	0.029*
C12D	0.25918 (13)	0.32856 (10)	0.30002 (14)	0.0251 (4)
H12G	0.2115	0.3225	0.3459	0.030*
H12H	0.2388	0.3064	0.2438	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0192 (3)	0.0217 (2)	0.0218 (2)	0.00158 (19)	−0.00060 (19)	0.00124 (19)
N1A	0.0229 (9)	0.0207 (8)	0.0158 (8)	−0.0020 (7)	−0.0032 (7)	−0.0001 (6)
O1A	0.0189 (7)	0.0276 (7)	0.0167 (7)	0.0021 (6)	0.0016 (5)	0.0027 (5)
C1A	0.0153 (10)	0.0201 (9)	0.0184 (9)	0.0006 (8)	0.0034 (7)	−0.0018 (7)
C2A	0.0263 (11)	0.0194 (10)	0.0300 (11)	0.0023 (8)	0.0079 (9)	0.0025 (8)
C3A	0.0294 (12)	0.0214 (10)	0.0307 (11)	−0.0036 (9)	0.0067 (9)	−0.0053 (8)
C4A	0.0205 (11)	0.0248 (10)	0.0233 (10)	−0.0016 (8)	−0.0002 (8)	−0.0045 (8)
C5A	0.0150 (10)	0.0227 (10)	0.0167 (9)	0.0010 (8)	0.0013 (7)	−0.0007 (7)
C6A	0.0143 (10)	0.0220 (10)	0.0144 (9)	0.0008 (7)	0.0018 (7)	0.0012 (7)
C7A	0.0181 (10)	0.0229 (10)	0.0238 (10)	0.0017 (8)	−0.0022 (8)	−0.0027 (8)
C8A	0.0189 (10)	0.0224 (10)	0.0176 (9)	−0.0030 (8)	0.0026 (8)	−0.0004 (7)
C9A	0.0210 (10)	0.0176 (9)	0.0199 (10)	−0.0012 (8)	0.0019 (8)	0.0001 (7)
C10A	0.0176 (10)	0.0193 (9)	0.0148 (9)	0.0009 (8)	0.0019 (7)	0.0024 (7)
C11A	0.0242 (11)	0.0236 (10)	0.0194 (10)	−0.0018 (8)	0.0042 (8)	−0.0042 (8)
C12A	0.0295 (12)	0.0265 (11)	0.0135 (9)	−0.0049 (9)	0.0009 (8)	−0.0010 (8)
S1B	0.0223 (3)	0.0215 (2)	0.0215 (3)	0.0001 (2)	0.0020 (2)	−0.00228 (19)
N1B	0.0188 (9)	0.0203 (8)	0.0189 (8)	−0.0002 (7)	0.0030 (7)	0.0005 (6)
O1B	0.0180 (7)	0.0315 (8)	0.0181 (7)	0.0065 (6)	0.0015 (5)	−0.0007 (6)
C1B	0.0181 (10)	0.0247 (10)	0.0144 (9)	−0.0003 (8)	−0.0012 (7)	0.0002 (7)
C2B	0.0323 (12)	0.0186 (10)	0.0310 (11)	−0.0001 (9)	−0.0037 (9)	−0.0029 (8)
C3B	0.0339 (13)	0.0230 (11)	0.0314 (12)	−0.0063 (9)	−0.0008 (10)	0.0038 (9)
C4B	0.0266 (11)	0.0252 (10)	0.0219 (10)	−0.0041 (9)	0.0023 (8)	0.0016 (8)
C5B	0.0170 (10)	0.0234 (10)	0.0141 (9)	0.0006 (8)	0.0014 (7)	−0.0001 (7)
C6B	0.0146 (10)	0.0232 (10)	0.0140 (9)	0.0011 (7)	−0.0014 (7)	−0.0006 (7)
C7B	0.0234 (11)	0.0246 (10)	0.0163 (9)	−0.0039 (8)	0.0028 (8)	−0.0014 (7)
C8B	0.0194 (10)	0.0261 (11)	0.0175 (10)	0.0013 (8)	−0.0004 (8)	0.0025 (8)
C9B	0.0213 (10)	0.0186 (9)	0.0195 (10)	0.0010 (8)	0.0001 (8)	−0.0001 (7)
C10B	0.0171 (10)	0.0230 (10)	0.0152 (9)	0.0030 (8)	−0.0007 (7)	−0.0012 (7)
C11B	0.0180 (10)	0.0204 (10)	0.0204 (10)	−0.0017 (8)	−0.0020 (8)	0.0013 (7)
C12B	0.0163 (10)	0.0206 (10)	0.0267 (10)	0.0016 (8)	0.0027 (8)	0.0020 (8)
S1C	0.0210 (3)	0.0235 (2)	0.0194 (2)	−0.0027 (2)	0.00001 (19)	−0.00086 (19)
N1C	0.0174 (9)	0.0220 (8)	0.0182 (8)	−0.0004 (7)	−0.0030 (6)	−0.0011 (6)
O1C	0.0186 (7)	0.0299 (7)	0.0169 (7)	−0.0016 (6)	0.0008 (5)	−0.0055 (6)
C1C	0.0157 (10)	0.0252 (10)	0.0169 (9)	0.0003 (8)	0.0016 (7)	−0.0016 (7)
C2C	0.0281 (12)	0.0232 (10)	0.0277 (11)	−0.0033 (9)	0.0078 (9)	−0.0039 (8)
C3C	0.0261 (12)	0.0226 (11)	0.0309 (11)	0.0044 (9)	0.0077 (9)	0.0032 (8)
C4C	0.0202 (11)	0.0275 (11)	0.0238 (10)	0.0031 (8)	0.0010 (8)	0.0027 (8)
C5C	0.0161 (10)	0.0242 (10)	0.0174 (9)	−0.0014 (8)	0.0013 (7)	−0.0017 (7)
C6C	0.0155 (10)	0.0241 (10)	0.0147 (9)	−0.0003 (8)	0.0021 (7)	−0.0010 (7)
C7C	0.0161 (10)	0.0279 (11)	0.0223 (10)	−0.0010 (8)	−0.0015 (8)	0.0025 (8)
C8C	0.0193 (10)	0.0267 (11)	0.0178 (10)	0.0034 (8)	0.0019 (8)	0.0005 (8)
C9C	0.0222 (11)	0.0176 (9)	0.0209 (10)	−0.0006 (8)	0.0000 (8)	−0.0009 (7)
C10C	0.0182 (10)	0.0233 (10)	0.0159 (9)	−0.0016 (8)	0.0018 (7)	−0.0034 (7)
C11C	0.0236 (11)	0.0258 (11)	0.0179 (10)	−0.0014 (8)	0.0016 (8)	0.0042 (8)
C12C	0.0236 (11)	0.0265 (11)	0.0151 (9)	0.0028 (8)	0.0005 (8)	−0.0019 (8)
S1D	0.0219 (3)	0.0238 (3)	0.0201 (3)	−0.0011 (2)	0.0026 (2)	0.00269 (19)
N1D	0.0214 (9)	0.0239 (9)	0.0190 (8)	−0.0009 (7)	0.0056 (7)	−0.0016 (6)
O1D	0.0182 (7)	0.0302 (8)	0.0176 (7)	−0.0036 (6)	0.0006 (5)	0.0017 (6)
C1D	0.0172 (10)	0.0249 (10)	0.0161 (9)	0.0000 (8)	−0.0017 (7)	0.0009 (7)
C2D	0.0280 (12)	0.0223 (10)	0.0289 (11)	−0.0027 (9)	−0.0037 (9)	0.0045 (8)
C3D	0.0311 (12)	0.0216 (10)	0.0247 (11)	0.0041 (9)	−0.0048 (9)	−0.0008 (8)
C4D	0.0255 (11)	0.0256 (10)	0.0182 (10)	0.0045 (9)	−0.0005 (8)	0.0005 (8)
C5D	0.0160 (10)	0.0241 (10)	0.0152 (9)	−0.0004 (8)	0.0018 (7)	0.0015 (7)
C6D	0.0160 (10)	0.0229 (10)	0.0151 (9)	−0.0009 (8)	−0.0003 (7)	0.0007 (7)
C7D	0.0268 (11)	0.0277 (11)	0.0156 (9)	0.0032 (9)	0.0030 (8)	−0.0003 (8)
C8D	0.0209 (11)	0.0238 (10)	0.0207 (10)	0.0012 (8)	−0.0007 (8)	−0.0034 (8)
C9D	0.0207 (10)	0.0185 (9)	0.0216 (10)	0.0010 (8)	0.0004 (8)	0.0012 (7)
C10D	0.0157 (10)	0.0215 (10)	0.0170 (9)	−0.0010 (8)	0.0002 (8)	0.0014 (7)
C11D	0.0181 (10)	0.0301 (11)	0.0231 (10)	0.0047 (8)	−0.0017 (8)	−0.0007 (8)
C12D	0.0180 (11)	0.0302 (11)	0.0272 (11)	−0.0005 (8)	0.0038 (8)	−0.0035 (8)

Geometric parameters (Å, º)

S1A—C2A	1.718 (2)	S1C—C2C	1.714 (2)
S1A—C1A	1.7350 (19)	S1C—C1C	1.7357 (19)
N1A—C6A	1.440 (2)	N1C—C6C	1.436 (2)
N1A—C7A	1.480 (2)	N1C—C12C	1.477 (2)
N1A—C12A	1.482 (2)	N1C—C7C	1.482 (2)
O1A—C10A	1.431 (2)	O1C—C10C	1.431 (2)
O1A—H1A	0.8400	O1C—H1C	0.8400
C1A—C4A	1.377 (3)	C1C—C4C	1.375 (3)
C1A—C5A	1.456 (3)	C1C—C5C	1.458 (3)
C2A—C3A	1.357 (3)	C2C—C3C	1.361 (3)
C2A—H2A	0.9500	C2C—H2C	0.9500
C3A—C4A	1.412 (3)	C3C—C4C	1.417 (3)
C3A—H3A	0.9500	C3C—H3C	0.9500
C4A—H4A	0.9500	C4C—H4C	0.9500
C5A—C6A	1.333 (2)	C5C—C6C	1.335 (3)
C5A—H5A	0.9500	C5C—H5C	0.9500
C6A—C10A	1.523 (2)	C6C—C10C	1.519 (3)
C7A—C8A	1.550 (3)	C7C—C8C	1.548 (3)
C7A—H7A1	0.9900	C7C—H7C1	0.9900
C7A—H7A2	0.9900	C7C—H7C2	0.9900
C8A—C9A	1.537 (3)	C8C—C9C	1.535 (3)
C8A—H8A1	0.9900	C8C—H8C1	0.9900
C8A—H8A2	0.9900	C8C—H8C2	0.9900
C9A—C10A	1.530 (2)	C9C—C10C	1.534 (3)
C9A—C11A	1.531 (2)	C9C—C11C	1.534 (2)
C9A—H9A	1.0000	C9C—H9C	1.0000
C10A—H10A	1.0000	C10C—H10C	1.0000
C11A—C12A	1.549 (3)	C11C—C12C	1.552 (3)
C11A—H11A	0.9900	C11C—H11E	0.9900
C11A—H11B	0.9900	C11C—H11F	0.9900
C12A—H12A	0.9900	C12C—H12E	0.9900
C12A—H12B	0.9900	C12C—H12F	0.9900
S1B—C2B	1.717 (2)	S1D—C2D	1.718 (2)
S1B—C1B	1.7348 (19)	S1D—C1D	1.7373 (19)
N1B—C6B	1.442 (2)	N1D—C6D	1.438 (2)
N1B—C12B	1.481 (2)	N1D—C12D	1.481 (2)
N1B—C7B	1.483 (2)	N1D—C7D	1.484 (2)
O1B—C10B	1.435 (2)	O1D—C10D	1.430 (2)
O1B—H1B	0.8400	O1D—H1D	0.8400
C1B—C4B	1.377 (3)	C1D—C4D	1.372 (3)
C1B—C5B	1.455 (3)	C1D—C5D	1.451 (3)
C2B—C3B	1.354 (3)	C2D—C3D	1.360 (3)
C2B—H2B	0.9500	C2D—H2D	0.9500
C3B—C4B	1.420 (3)	C3D—C4D	1.415 (3)
C3B—H3B	0.9500	C3D—H3D	0.9500
C4B—H4B	0.9500	C4D—H4D	0.9500
C5B—C6B	1.333 (3)	C5D—C6D	1.332 (3)
C5B—H5B	0.9500	C5D—H5D	0.9500
C6B—C10B	1.516 (2)	C6D—C10D	1.522 (2)
C7B—C8B	1.549 (3)	C7D—C8D	1.551 (3)
C7B—H7B1	0.9900	C7D—H7D1	0.9900
C7B—H7B2	0.9900	C7D—H7D2	0.9900
C8B—C9B	1.538 (2)	C8D—C9D	1.538 (3)
C8B—H8B1	0.9900	C8D—H8D1	0.9900
C8B—H8B2	0.9900	C8D—H8D2	0.9900
C9B—C10B	1.530 (3)	C9D—C11D	1.532 (3)
C9B—C11B	1.533 (3)	C9D—C10D	1.534 (3)
C9B—H9B	1.0000	C9D—H9D	1.0000
C10B—H10B	1.0000	C10D—H10D	1.0000
C11B—C12B	1.545 (2)	C11D—C12D	1.548 (3)
C11B—H11C	0.9900	C11D—H11G	0.9900
C11B—H11D	0.9900	C11D—H11H	0.9900
C12B—H12C	0.9900	C12D—H12G	0.9900
C12B—H12D	0.9900	C12D—H12H	0.9900
C2A—S1A—C1A	91.66 (9)	C2C—S1C—C1C	91.60 (10)
C6A—N1A—C7A	107.28 (14)	C6C—N1C—C12C	108.88 (14)
C6A—N1A—C12A	109.25 (15)	C6C—N1C—C7C	107.69 (14)
C7A—N1A—C12A	108.86 (14)	C12C—N1C—C7C	108.94 (14)
C10A—O1A—H1A	109.5	C10C—O1C—H1C	109.5
C4A—C1A—C5A	125.21 (18)	C4C—C1C—C5C	124.91 (18)
C4A—C1A—S1A	110.39 (14)	C4C—C1C—S1C	110.58 (15)
C5A—C1A—S1A	124.39 (14)	C5C—C1C—S1C	124.48 (14)
C3A—C2A—S1A	112.08 (15)	C3C—C2C—S1C	112.39 (15)
C3A—C2A—H2A	124.0	C3C—C2C—H2C	123.8
S1A—C2A—H2A	124.0	S1C—C2C—H2C	123.8
C2A—C3A—C4A	112.69 (18)	C2C—C3C—C4C	112.26 (18)
C2A—C3A—H3A	123.7	C2C—C3C—H3C	123.9
C4A—C3A—H3A	123.7	C4C—C3C—H3C	123.9
C1A—C4A—C3A	113.17 (18)	C1C—C4C—C3C	113.17 (18)
C1A—C4A—H4A	123.4	C1C—C4C—H4C	123.4
C3A—C4A—H4A	123.4	C3C—C4C—H4C	123.4
C6A—C5A—C1A	126.55 (17)	C6C—C5C—C1C	126.38 (18)
C6A—C5A—H5A	116.7	C6C—C5C—H5C	116.8
C1A—C5A—H5A	116.7	C1C—C5C—H5C	116.8
C5A—C6A—N1A	120.69 (16)	C5C—C6C—N1C	120.39 (17)
C5A—C6A—C10A	125.26 (17)	C5C—C6C—C10C	125.30 (17)
N1A—C6A—C10A	114.02 (15)	N1C—C6C—C10C	114.31 (15)
N1A—C7A—C8A	111.32 (15)	N1C—C7C—C8C	111.46 (15)
N1A—C7A—H7A1	109.4	N1C—C7C—H7C1	109.3
C8A—C7A—H7A1	109.4	C8C—C7C—H7C1	109.3
N1A—C7A—H7A2	109.4	N1C—C7C—H7C2	109.3
C8A—C7A—H7A2	109.4	C8C—C7C—H7C2	109.3
H7A1—C7A—H7A2	108.0	H7C1—C7C—H7C2	108.0
C9A—C8A—C7A	108.52 (15)	C9C—C8C—C7C	108.45 (15)
C9A—C8A—H8A1	110.0	C9C—C8C—H8C1	110.0
C7A—C8A—H8A1	110.0	C7C—C8C—H8C1	110.0
C9A—C8A—H8A2	110.0	C9C—C8C—H8C2	110.0
C7A—C8A—H8A2	110.0	C7C—C8C—H8C2	110.0
H8A1—C8A—H8A2	108.4	H8C1—C8C—H8C2	108.4
C10A—C9A—C11A	107.41 (15)	C10C—C9C—C11C	107.67 (15)
C10A—C9A—C8A	110.11 (15)	C10C—C9C—C8C	110.16 (15)
C11A—C9A—C8A	108.05 (15)	C11C—C9C—C8C	107.87 (15)
C10A—C9A—H9A	110.4	C10C—C9C—H9C	110.4
C11A—C9A—H9A	110.4	C11C—C9C—H9C	110.4
C8A—C9A—H9A	110.4	C8C—C9C—H9C	110.4
O1A—C10A—C6A	112.68 (14)	O1C—C10C—C6C	113.42 (15)
O1A—C10A—C9A	113.84 (14)	O1C—C10C—C9C	114.06 (15)
C6A—C10A—C9A	107.16 (15)	C6C—C10C—C9C	107.20 (15)
O1A—C10A—H10A	107.6	O1C—C10C—H10C	107.3
C6A—C10A—H10A	107.6	C6C—C10C—H10C	107.3
C9A—C10A—H10A	107.6	C9C—C10C—H10C	107.3
C9A—C11A—C12A	107.79 (14)	C9C—C11C—C12C	107.51 (14)
C9A—C11A—H11A	110.1	C9C—C11C—H11E	110.2
C12A—C11A—H11A	110.1	C12C—C11C—H11E	110.2
C9A—C11A—H11B	110.1	C9C—C11C—H11F	110.2
C12A—C11A—H11B	110.1	C12C—C11C—H11F	110.2
H11A—C11A—H11B	108.5	H11E—C11C—H11F	108.5
N1A—C12A—C11A	112.05 (14)	N1C—C12C—C11C	112.22 (14)
N1A—C12A—H12A	109.2	N1C—C12C—H12E	109.2
C11A—C12A—H12A	109.2	C11C—C12C—H12E	109.2
N1A—C12A—H12B	109.2	N1C—C12C—H12F	109.2
C11A—C12A—H12B	109.2	C11C—C12C—H12F	109.2
H12A—C12A—H12B	107.9	H12E—C12C—H12F	107.9
C2B—S1B—C1B	91.69 (10)	C2D—S1D—C1D	91.77 (10)
C6B—N1B—C12B	109.03 (14)	C6D—N1D—C12D	108.30 (14)
C6B—N1B—C7B	107.48 (14)	C6D—N1D—C7D	108.19 (15)
C12B—N1B—C7B	108.64 (14)	C12D—N1D—C7D	108.65 (15)
C10B—O1B—H1B	109.5	C10D—O1D—H1D	109.5
C4B—C1B—C5B	124.91 (18)	C4D—C1D—C5D	125.18 (17)
C4B—C1B—S1B	110.36 (15)	C4D—C1D—S1D	110.13 (14)
C5B—C1B—S1B	124.72 (14)	C5D—C1D—S1D	124.67 (14)
C3B—C2B—S1B	112.43 (16)	C3D—C2D—S1D	112.20 (15)
C3B—C2B—H2B	123.8	C3D—C2D—H2D	123.9
S1B—C2B—H2B	123.8	S1D—C2D—H2D	123.9
C2B—C3B—C4B	112.31 (18)	C2D—C3D—C4D	112.14 (18)
C2B—C3B—H3B	123.8	C2D—C3D—H3D	123.9
C4B—C3B—H3B	123.8	C4D—C3D—H3D	123.9
C1B—C4B—C3B	113.21 (19)	C1D—C4D—C3D	113.75 (18)
C1B—C4B—H4B	123.4	C1D—C4D—H4D	123.1
C3B—C4B—H4B	123.4	C3D—C4D—H4D	123.1
C6B—C5B—C1B	127.41 (17)	C6D—C5D—C1D	127.25 (17)
C6B—C5B—H5B	116.3	C6D—C5D—H5D	116.4
C1B—C5B—H5B	116.3	C1D—C5D—H5D	116.4
C5B—C6B—N1B	120.61 (16)	C5D—C6D—N1D	120.46 (17)
C5B—C6B—C10B	125.22 (17)	C5D—C6D—C10D	125.02 (17)
N1B—C6B—C10B	114.17 (15)	N1D—C6D—C10D	114.52 (15)
N1B—C7B—C8B	111.49 (14)	N1D—C7D—C8D	111.82 (15)
N1B—C7B—H7B1	109.3	N1D—C7D—H7D1	109.3
C8B—C7B—H7B1	109.3	C8D—C7D—H7D1	109.3
N1B—C7B—H7B2	109.3	N1D—C7D—H7D2	109.3
C8B—C7B—H7B2	109.3	C8D—C7D—H7D2	109.3
H7B1—C7B—H7B2	108.0	H7D1—C7D—H7D2	107.9
C9B—C8B—C7B	108.55 (15)	C9D—C8D—C7D	108.16 (15)
C9B—C8B—H8B1	110.0	C9D—C8D—H8D1	110.1
C7B—C8B—H8B1	110.0	C7D—C8D—H8D1	110.1
C9B—C8B—H8B2	110.0	C9D—C8D—H8D2	110.1
C7B—C8B—H8B2	110.0	C7D—C8D—H8D2	110.1
H8B1—C8B—H8B2	108.4	H8D1—C8D—H8D2	108.4
C10B—C9B—C11B	107.87 (15)	C11D—C9D—C10D	107.90 (15)
C10B—C9B—C8B	109.66 (15)	C11D—C9D—C8D	108.10 (15)
C11B—C9B—C8B	107.56 (15)	C10D—C9D—C8D	109.45 (15)
C10B—C9B—H9B	110.6	C11D—C9D—H9D	110.4
C11B—C9B—H9B	110.6	C10D—C9D—H9D	110.4
C8B—C9B—H9B	110.6	C8D—C9D—H9D	110.4
O1B—C10B—C6B	113.49 (15)	O1D—C10D—C6D	113.23 (15)
O1B—C10B—C9B	113.60 (15)	O1D—C10D—C9D	113.75 (15)
C6B—C10B—C9B	107.66 (14)	C6D—C10D—C9D	107.33 (14)
O1B—C10B—H10B	107.2	O1D—C10D—H10D	107.4
C6B—C10B—H10B	107.2	C6D—C10D—H10D	107.4
C9B—C10B—H10B	107.2	C9D—C10D—H10D	107.4
C9B—C11B—C12B	108.04 (15)	C9D—C11D—C12D	108.27 (15)
C9B—C11B—H11C	110.1	C9D—C11D—H11G	110.0
C12B—C11B—H11C	110.1	C12D—C11D—H11G	110.0
C9B—C11B—H11D	110.1	C9D—C11D—H11H	110.0
C12B—C11B—H11D	110.1	C12D—C11D—H11H	110.0
H11C—C11B—H11D	108.4	H11G—C11D—H11H	108.4
N1B—C12B—C11B	112.18 (15)	N1D—C12D—C11D	111.89 (15)
N1B—C12B—H12C	109.2	N1D—C12D—H12G	109.2
C11B—C12B—H12C	109.2	C11D—C12D—H12G	109.2
N1B—C12B—H12D	109.2	N1D—C12D—H12H	109.2
C11B—C12B—H12D	109.2	C11D—C12D—H12H	109.2
H12C—C12B—H12D	107.9	H12G—C12D—H12H	107.9
C2A—S1A—C1A—C4A	0.63 (15)	C2C—S1C—C1C—C4C	−0.41 (15)
C2A—S1A—C1A—C5A	179.96 (16)	C2C—S1C—C1C—C5C	177.82 (16)
C1A—S1A—C2A—C3A	−1.00 (16)	C1C—S1C—C2C—C3C	0.08 (16)
S1A—C2A—C3A—C4A	1.1 (2)	S1C—C2C—C3C—C4C	0.3 (2)
C5A—C1A—C4A—C3A	−179.45 (17)	C5C—C1C—C4C—C3C	−177.59 (17)
S1A—C1A—C4A—C3A	−0.1 (2)	S1C—C1C—C4C—C3C	0.6 (2)
C2A—C3A—C4A—C1A	−0.6 (3)	C2C—C3C—C4C—C1C	−0.6 (2)
C4A—C1A—C5A—C6A	170.67 (19)	C4C—C1C—C5C—C6C	173.41 (19)
S1A—C1A—C5A—C6A	−8.6 (3)	S1C—C1C—C5C—C6C	−4.6 (3)
C1A—C5A—C6A—N1A	2.2 (3)	C1C—C5C—C6C—N1C	2.9 (3)
C1A—C5A—C6A—C10A	−179.73 (17)	C1C—C5C—C6C—C10C	−178.20 (17)
C7A—N1A—C6A—C5A	111.00 (18)	C12C—N1C—C6C—C5C	−128.63 (18)
C12A—N1A—C6A—C5A	−131.14 (18)	C7C—N1C—C6C—C5C	113.38 (19)
C7A—N1A—C6A—C10A	−67.25 (18)	C12C—N1C—C6C—C10C	52.37 (19)
C12A—N1A—C6A—C10A	50.61 (19)	C7C—N1C—C6C—C10C	−65.61 (19)
C6A—N1A—C7A—C8A	55.71 (19)	C6C—N1C—C7C—C8C	56.25 (19)
C12A—N1A—C7A—C8A	−62.40 (19)	C12C—N1C—C7C—C8C	−61.69 (19)
N1A—C7A—C8A—C9A	5.5 (2)	N1C—C7C—C8C—C9C	4.2 (2)
C7A—C8A—C9A—C10A	−60.27 (19)	C7C—C8C—C9C—C10C	−59.53 (19)
C7A—C8A—C9A—C11A	56.76 (19)	C7C—C8C—C9C—C11C	57.73 (19)
C5A—C6A—C10A—O1A	−40.2 (2)	C5C—C6C—C10C—O1C	−42.3 (3)
N1A—C6A—C10A—O1A	137.97 (15)	N1C—C6C—C10C—O1C	136.65 (16)
C5A—C6A—C10A—C9A	−166.16 (17)	C5C—C6C—C10C—C9C	−169.10 (17)
N1A—C6A—C10A—C9A	12.0 (2)	N1C—C6C—C10C—C9C	9.8 (2)
C11A—C9A—C10A—O1A	168.29 (15)	C11C—C9C—C10C—O1C	168.46 (15)
C8A—C9A—C10A—O1A	−74.29 (19)	C8C—C9C—C10C—O1C	−74.16 (19)
C11A—C9A—C10A—C6A	−66.43 (18)	C11C—C9C—C10C—C6C	−65.10 (18)
C8A—C9A—C10A—C6A	51.00 (18)	C8C—C9C—C10C—C6C	52.28 (19)
C10A—C9A—C11A—C12A	55.25 (19)	C10C—C9C—C11C—C12C	55.40 (19)
C8A—C9A—C11A—C12A	−63.51 (19)	C8C—C9C—C11C—C12C	−63.46 (19)
C6A—N1A—C12A—C11A	−61.5 (2)	C6C—N1C—C12C—C11C	−61.6 (2)
C7A—N1A—C12A—C11A	55.3 (2)	C7C—N1C—C12C—C11C	55.6 (2)
C9A—C11A—C12A—N1A	7.0 (2)	C9C—C11C—C12C—N1C	6.4 (2)
C2B—S1B—C1B—C4B	0.61 (15)	C2D—S1D—C1D—C4D	0.42 (15)
C2B—S1B—C1B—C5B	−178.40 (17)	C2D—S1D—C1D—C5D	178.67 (17)
C1B—S1B—C2B—C3B	−0.81 (17)	C1D—S1D—C2D—C3D	−0.68 (16)
S1B—C2B—C3B—C4B	0.8 (2)	S1D—C2D—C3D—C4D	0.8 (2)
C5B—C1B—C4B—C3B	178.73 (18)	C5D—C1D—C4D—C3D	−178.31 (18)
S1B—C1B—C4B—C3B	−0.3 (2)	S1D—C1D—C4D—C3D	−0.1 (2)
C2B—C3B—C4B—C1B	−0.3 (3)	C2D—C3D—C4D—C1D	−0.4 (3)
C4B—C1B—C5B—C6B	173.55 (19)	C4D—C1D—C5D—C6D	170.85 (19)
S1B—C1B—C5B—C6B	−7.6 (3)	S1D—C1D—C5D—C6D	−7.1 (3)
C1B—C5B—C6B—N1B	0.9 (3)	C1D—C5D—C6D—N1D	2.4 (3)
C1B—C5B—C6B—C10B	−179.20 (17)	C1D—C5D—C6D—C10D	−176.59 (17)
C12B—N1B—C6B—C5B	−128.06 (18)	C12D—N1D—C6D—C5D	−125.11 (18)
C7B—N1B—C6B—C5B	114.36 (18)	C7D—N1D—C6D—C5D	117.29 (19)
C12B—N1B—C6B—C10B	52.07 (19)	C12D—N1D—C6D—C10D	54.0 (2)
C7B—N1B—C6B—C10B	−65.52 (18)	C7D—N1D—C6D—C10D	−63.62 (19)
C6B—N1B—C7B—C8B	56.04 (19)	C6D—N1D—C7D—C8D	55.1 (2)
C12B—N1B—C7B—C8B	−61.79 (19)	C12D—N1D—C7D—C8D	−62.3 (2)
N1B—C7B—C8B—C9B	4.5 (2)	N1D—C7D—C8D—C9D	5.2 (2)
C7B—C8B—C9B—C10B	−59.73 (19)	C7D—C8D—C9D—C11D	56.62 (19)
C7B—C8B—C9B—C11B	57.32 (19)	C7D—C8D—C9D—C10D	−60.66 (19)
C5B—C6B—C10B—O1B	−43.6 (2)	C5D—C6D—C10D—O1D	−46.9 (2)
N1B—C6B—C10B—O1B	136.29 (15)	N1D—C6D—C10D—O1D	134.07 (16)
C5B—C6B—C10B—C9B	−170.19 (17)	C5D—C6D—C10D—C9D	−173.26 (18)
N1B—C6B—C10B—C9B	9.7 (2)	N1D—C6D—C10D—C9D	7.7 (2)
C11B—C9B—C10B—O1B	169.01 (14)	C11D—C9D—C10D—O1D	170.63 (14)
C8B—C9B—C10B—O1B	−74.14 (19)	C8D—C9D—C10D—O1D	−71.97 (19)
C11B—C9B—C10B—C6B	−64.44 (18)	C11D—C9D—C10D—C6D	−63.32 (18)
C8B—C9B—C10B—C6B	52.42 (19)	C8D—C9D—C10D—C6D	54.09 (19)
C10B—C9B—C11B—C12B	54.84 (19)	C10D—C9D—C11D—C12D	55.07 (19)
C8B—C9B—C11B—C12B	−63.37 (19)	C8D—C9D—C11D—C12D	−63.20 (19)
C6B—N1B—C12B—C11B	−61.27 (19)	C6D—N1D—C12D—C11D	−61.81 (19)
C7B—N1B—C12B—C11B	55.58 (19)	C7D—N1D—C12D—C11D	55.49 (19)
C9B—C11B—C12B—N1B	6.5 (2)	C9D—C11D—C12D—N1D	6.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1B	0.84	1.97	2.7734 (18)	161
O1B—H1B···O1C	0.84	2.02	2.8124 (18)	157
O1C—H1C···O1D	0.84	1.97	2.7812 (18)	163
O1D—H1D···O1A	0.84	1.97	2.7795 (18)	162