Crystal structure of (E)-4-(acet-oxy-imino)-N-allyl-3-isopropyl-2,6-di-phenyl-piperi-dine-1-carbo-thio-amide.

The title compound, C26H31N3O2S, crystallizes with two mol-ecules (A and B) in the asymmetric unit. In each case, the piperidine ring exists in a twist-boat conformation. The dihedral angle between the phenyl rings is 46.16 (12)° in mol-ecule A and 44.95 (12)° in mol-ecule B. In both mol-ecules, the allyl side chain is disordered over two orientations in a 0.649 (9):0.351 (9) ratio for mol-ecule A and 0.826 (10):0.174 (10) ratio for mol-ecule B. In the crystal, neither mol-ecule forms a hydrogen bond from its N-H group, presumably due to steric hindrance. A+A and B+B inversion dimers are formed, linked by pairs of weak C-H⋯O hydrogen bonds enclosing R 2 (2)(22) ring motifs.

Related literature

For the structural properties and biological potentials of carbothio­amides, see: Wilkerson et al. (1996 ▸); Koca et al. (2013 ▸); Liu et al. (2012 ▸); Malik et al.(2013 ▸). For related structures, see: Park et al. (2012a ▸,b ▸).

Experimental

Crystal data

C26H31N3O2S

M = 449.60

Triclinic,

a = 12.0434 (6) Å

b = 14.0479 (7) Å

c = 15.2740 (7) Å

α = 82.161 (2)°

β = 72.463 (2)°

γ = 80.094 (2)°

V = 2417.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 293 K

0.28 × 0.25 × 0.24 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▸) T min = 0.956, T max = 0.962

74637 measured reflections

11303 independent reflections

6065 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.146

S = 1.01

11303 reflections

627 parameters

93 restraints

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2008 ▸); cell refinement: SAINT (Bruker, 2008 ▸); data reduction: SAINT; 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 Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015012499/su5159sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015012499/su5159Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015012499/su5159Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015012499/su5159fig1.tif

The mol­ecular structure of mol­ecule A of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015012499/su5159fig2.tif

The mol­ecular structure of mol­ecule B of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015012499/su5159fig3.tif

A partial view of the crystal packing of the title compound, with the C—H⋯O hydrogen bonds shown as dashed lines (see Table 1 for details). Other H atoms and the minor components of the allyl groups have been omitted for clarity.

CCDC reference: 1024973

Additional supporting information: crystallographic information; 3D view; checkCIF report

C26H31N3O2S	Z = 4
Mr = 449.60	F(000) = 960
Triclinic, P1	Dx = 1.235 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.0434 (6) Å	Cell parameters from 6065 reflections
b = 14.0479 (7) Å	θ = 1.5–27.8°
c = 15.2740 (7) Å	µ = 0.16 mm−1
α = 82.161 (2)°	T = 293 K
β = 72.463 (2)°	Block, colourless
γ = 80.094 (2)°	0.28 × 0.25 × 0.24 mm
V = 2417.4 (2) Å3

Bruker Kappa APEXII CCD diffractometer	11303 independent reflections
Radiation source: fine-focus sealed tube	6065 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
ω & φ scans	θmax = 27.8°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
Tmin = 0.956, Tmax = 0.962	k = −18→18
74637 measured reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049	Hydrogen site location: mixed
wR(F2) = 0.146	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0578P)2 + 0.7614P] where P = (Fo2 + 2Fc2)/3
11303 reflections	(Δ/σ)max = 0.001
627 parameters	Δρmax = 0.19 e Å−3
93 restraints	Δρmin = −0.24 e Å−3

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.

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.9104 (2)	0.32104 (16)	0.16483 (16)	0.0505 (6)
H1	0.8287	0.3293	0.1823	0.061*
C2	0.9726 (3)	0.25361 (18)	0.10359 (18)	0.0634 (7)
H2	0.9324	0.2168	0.0804	0.076*
C3	1.0929 (3)	0.24062 (19)	0.07682 (18)	0.0679 (8)
H3	1.1347	0.1957	0.0350	0.082*
C4	1.1506 (2)	0.29384 (19)	0.11184 (19)	0.0666 (8)
H4	1.2324	0.2848	0.0942	0.080*
C5	1.0898 (2)	0.36120 (17)	0.17328 (17)	0.0546 (6)
H5	1.1309	0.3968	0.1967	0.065*
C6	0.96801 (19)	0.37627 (15)	0.20040 (14)	0.0414 (5)
C7	0.89823 (17)	0.44607 (15)	0.27223 (14)	0.0392 (5)
H7	0.8777	0.4069	0.3315	0.047*
C8	0.96601 (18)	0.52344 (15)	0.28429 (14)	0.0398 (5)
H8	1.0386	0.4899	0.2971	0.048*
C9	1.00053 (18)	0.58243 (14)	0.19289 (14)	0.0394 (5)
C10	0.91588 (18)	0.59728 (15)	0.13722 (14)	0.0410 (5)
H10C	0.9416	0.5509	0.0911	0.049*
H10D	0.9167	0.6618	0.1052	0.049*
C11	0.78954 (17)	0.58595 (14)	0.19439 (13)	0.0375 (5)
H11	0.7606	0.6397	0.2338	0.045*
C12	0.71303 (18)	0.59542 (15)	0.13008 (14)	0.0400 (5)
C13	0.7181 (2)	0.52194 (17)	0.07673 (16)	0.0521 (6)
H13	0.7691	0.4647	0.0799	0.063*
C14	0.6473 (2)	0.5336 (2)	0.01873 (18)	0.0650 (7)
H14	0.6509	0.4839	−0.0168	0.078*
C15	0.5724 (2)	0.6170 (2)	0.01290 (19)	0.0692 (8)
H15	0.5240	0.6235	−0.0255	0.083*
C16	0.5684 (2)	0.6912 (2)	0.06366 (19)	0.0648 (7)
H16	0.5184	0.7487	0.0588	0.078*
C17	0.6389 (2)	0.68088 (17)	0.12239 (16)	0.0514 (6)
H17	0.6362	0.7316	0.1566	0.062*
C18	0.68301 (18)	0.46797 (15)	0.31362 (14)	0.0403 (5)
C19	0.4679 (7)	0.5156 (14)	0.3736 (6)	0.055 (2)	0.649 (9)
H19A	0.4322	0.5710	0.4089	0.066*	0.649 (9)
H19B	0.4741	0.4591	0.4171	0.066*	0.649 (9)
C20	0.3887 (7)	0.5005 (5)	0.3198 (4)	0.073 (2)	0.649 (9)
H20A	0.3097	0.5017	0.3523	0.088*	0.649 (9)
C21	0.4150 (8)	0.4867 (6)	0.2373 (4)	0.107 (3)	0.649 (9)
H21A	0.4926	0.4847	0.2011	0.129*	0.649 (9)
H21B	0.3570	0.4782	0.2115	0.129*	0.649 (9)
C19A	0.4658 (12)	0.509 (2)	0.3549 (12)	0.051 (4)	0.351 (9)
H19C	0.4126	0.5685	0.3711	0.061*	0.351 (9)
H19D	0.4597	0.4656	0.4106	0.061*	0.351 (9)
C20A	0.4303 (10)	0.4633 (11)	0.2866 (13)	0.080 (4)	0.351 (9)
H20C	0.4864	0.4176	0.2531	0.096*	0.351 (9)
C21A	0.3336 (10)	0.4799 (8)	0.2700 (9)	0.094 (4)	0.351 (9)
H21C	0.2744	0.5250	0.3017	0.113*	0.351 (9)
H21D	0.3205	0.4471	0.2259	0.113*	0.351 (9)
C22	1.2103 (2)	0.71539 (19)	0.0584 (2)	0.0602 (7)
C23	1.2410 (3)	0.7428 (2)	0.1369 (2)	0.0812 (9)
H23A	1.2808	0.6869	0.1642	0.122*
H23B	1.1707	0.7672	0.1819	0.122*
H23C	1.2916	0.7921	0.1157	0.122*
C24	0.9001 (2)	0.58617 (17)	0.36463 (15)	0.0495 (6)
H24	0.8309	0.6245	0.3499	0.059*
C25	0.9766 (2)	0.65575 (19)	0.37572 (18)	0.0647 (7)
H25A	1.0489	0.6200	0.3838	0.097*
H25B	0.9362	0.6907	0.4287	0.097*
H25C	0.9934	0.7007	0.3217	0.097*
C26	0.8579 (3)	0.5235 (2)	0.45415 (17)	0.0723 (8)
H26A	0.9227	0.4780	0.4649	0.108*
H26B	0.7978	0.4890	0.4499	0.108*
H26C	0.8267	0.5640	0.5042	0.108*
N1	0.78573 (14)	0.49402 (11)	0.25558 (11)	0.0373 (4)
N2	0.58584 (15)	0.53170 (13)	0.31824 (13)	0.0453 (5)
H2A	0.590 (2)	0.5882 (13)	0.2876 (15)	0.054*
N3	1.10177 (16)	0.60888 (13)	0.16899 (12)	0.0471 (5)
S1	0.67667 (6)	0.35980 (4)	0.37701 (5)	0.05813 (19)
O1	1.12691 (13)	0.65613 (12)	0.07647 (11)	0.0552 (4)
O2	1.25123 (18)	0.74278 (16)	−0.02053 (15)	0.0901 (7)
C1'	0.6908 (2)	0.82063 (16)	0.39025 (18)	0.0530 (6)
H1'	0.6887	0.8289	0.3293	0.064*
C2'	0.6264 (2)	0.75462 (18)	0.4523 (2)	0.0675 (8)
H2'	0.5812	0.7192	0.4328	0.081*
C3'	0.6292 (3)	0.7414 (2)	0.5417 (2)	0.0747 (9)
H3'	0.5852	0.6976	0.5833	0.090*
C4'	0.6960 (3)	0.7921 (2)	0.56967 (19)	0.0746 (8)
H4'	0.6988	0.7822	0.6305	0.090*
C5'	0.7602 (2)	0.85858 (17)	0.50906 (16)	0.0579 (7)
H5'	0.8054	0.8931	0.5296	0.069*
C6'	0.75794 (18)	0.87427 (14)	0.41829 (15)	0.0418 (5)
C7'	0.83309 (19)	0.94263 (15)	0.34869 (14)	0.0407 (5)
H7'	0.9052	0.9025	0.3168	0.049*
C8'	0.87150 (18)	1.01997 (15)	0.39090 (15)	0.0430 (5)
H8'	0.9098	0.9862	0.4369	0.052*
C9'	0.76054 (19)	1.08015 (15)	0.44174 (15)	0.0413 (5)
C10'	0.66016 (18)	1.09535 (15)	0.40147 (14)	0.0418 (5)
H10A	0.6182	1.1601	0.4117	0.050*
H10B	0.6064	1.0495	0.4334	0.050*
C11'	0.69701 (17)	1.08337 (14)	0.29862 (14)	0.0376 (5)
H11'	0.7406	1.1369	0.2666	0.045*
C12'	0.58795 (18)	1.09288 (15)	0.26641 (13)	0.0387 (5)
C13'	0.5171 (2)	1.02040 (17)	0.28710 (17)	0.0523 (6)
H13'	0.5363	0.9635	0.3215	0.063*
C14'	0.4187 (2)	1.0319 (2)	0.2571 (2)	0.0654 (7)
H14'	0.3718	0.9827	0.2715	0.078*
C15'	0.3888 (2)	1.1149 (2)	0.20649 (19)	0.0663 (7)
H15'	0.3228	1.1217	0.1854	0.080*
C16'	0.4564 (2)	1.1878 (2)	0.18714 (18)	0.0644 (7)
H16'	0.4356	1.2450	0.1537	0.077*
C17'	0.5557 (2)	1.17704 (17)	0.21699 (15)	0.0513 (6)
H17'	0.6012	1.2272	0.2035	0.062*
C18'	0.82442 (18)	0.96574 (15)	0.18875 (15)	0.0426 (5)
C19'	0.8314 (2)	1.0136 (2)	0.02547 (16)	0.0624 (7)
H19E	0.8962	0.9610	0.0135	0.075*
H19F	0.8592	1.0713	−0.0113	0.075*
C20'	0.7370 (4)	0.9896 (3)	−0.0056 (3)	0.1015 (12)
H20E	0.7519	0.9936	−0.0693	0.122*	0.826 (10)
H20F	0.7353	0.9249	0.0174	0.122*	0.174 (10)
C21'	0.6441 (5)	0.9659 (5)	0.0372 (5)	0.130 (3)	0.826 (10)
H21E	0.6225	0.9602	0.1013	0.156*	0.826 (10)
H21F	0.5931	0.9530	0.0064	0.156*	0.826 (10)
C21B	0.6593 (18)	1.003 (2)	−0.0433 (18)	0.111 (9)	0.174 (10)
H21G	0.6414	1.0634	−0.0730	0.133*	0.174 (10)
H21H	0.6178	0.9527	−0.0424	0.133*	0.174 (10)
C22'	0.6484 (3)	1.21816 (19)	0.6224 (2)	0.0672 (8)
C23'	0.7637 (3)	1.2480 (3)	0.6141 (3)	0.1040 (12)
H23D	0.7529	1.2970	0.6551	0.156*
H23E	0.7973	1.2735	0.5518	0.156*
H23F	0.8154	1.1928	0.6299	0.156*
C24'	0.9607 (2)	1.07945 (18)	0.32045 (17)	0.0546 (6)
H24'	0.9267	1.1084	0.2706	0.066*
C25'	1.0733 (3)	1.0147 (2)	0.2795 (3)	0.0981 (11)
H25D	1.1302	1.0535	0.2399	0.147*
H25E	1.0581	0.9693	0.2443	0.147*
H25F	1.1033	0.9800	0.3281	0.147*
C26'	0.9864 (3)	1.1606 (2)	0.3641 (2)	0.0795 (9)
H26D	1.0106	1.1343	0.4179	0.119*
H26E	0.9168	1.2069	0.3813	0.119*
H26F	1.0481	1.1920	0.3207	0.119*
N1'	0.77728 (14)	0.99094 (12)	0.27709 (11)	0.0382 (4)
N2'	0.80050 (17)	1.03032 (14)	0.12168 (12)	0.0464 (5)
H2B	0.7510 (18)	1.0837 (13)	0.1341 (16)	0.056*
N3'	0.76056 (18)	1.10743 (14)	0.51771 (13)	0.0514 (5)
S1'	0.90805 (6)	0.85825 (5)	0.16427 (5)	0.0636 (2)
O1'	0.64564 (15)	1.15591 (12)	0.56286 (11)	0.0583 (4)
O2'	0.5553 (2)	1.24742 (16)	0.67412 (15)	0.0951 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0547 (15)	0.0396 (13)	0.0555 (14)	−0.0050 (11)	−0.0158 (12)	−0.0004 (11)
C2	0.088 (2)	0.0427 (14)	0.0590 (16)	−0.0050 (14)	−0.0216 (15)	−0.0058 (12)
C3	0.086 (2)	0.0431 (15)	0.0578 (16)	0.0035 (14)	−0.0022 (15)	−0.0052 (12)
C4	0.0585 (17)	0.0486 (15)	0.0714 (18)	0.0025 (13)	0.0057 (14)	−0.0008 (13)
C5	0.0480 (14)	0.0438 (13)	0.0638 (16)	−0.0055 (11)	−0.0050 (12)	−0.0031 (12)
C6	0.0415 (12)	0.0338 (11)	0.0417 (12)	−0.0031 (9)	−0.0059 (10)	0.0050 (9)
C7	0.0349 (11)	0.0383 (11)	0.0395 (11)	−0.0034 (9)	−0.0082 (9)	0.0054 (9)
C8	0.0346 (11)	0.0421 (12)	0.0419 (12)	−0.0029 (9)	−0.0131 (9)	0.0005 (9)
C9	0.0368 (12)	0.0357 (11)	0.0448 (12)	−0.0053 (9)	−0.0092 (10)	−0.0056 (9)
C10	0.0421 (12)	0.0394 (12)	0.0401 (12)	−0.0113 (10)	−0.0103 (10)	0.0049 (9)
C11	0.0417 (12)	0.0317 (11)	0.0370 (11)	−0.0052 (9)	−0.0108 (9)	0.0032 (9)
C12	0.0372 (12)	0.0403 (12)	0.0396 (12)	−0.0087 (9)	−0.0096 (9)	0.0076 (9)
C13	0.0595 (15)	0.0462 (14)	0.0549 (14)	−0.0103 (11)	−0.0240 (12)	0.0026 (11)
C14	0.0779 (19)	0.0685 (18)	0.0614 (16)	−0.0261 (15)	−0.0349 (15)	0.0058 (14)
C15	0.0659 (18)	0.089 (2)	0.0623 (17)	−0.0299 (17)	−0.0349 (15)	0.0215 (16)
C16	0.0457 (15)	0.0737 (19)	0.0645 (17)	0.0002 (13)	−0.0165 (13)	0.0205 (15)
C17	0.0465 (14)	0.0527 (14)	0.0488 (14)	−0.0010 (11)	−0.0122 (11)	0.0061 (11)
C18	0.0397 (12)	0.0403 (12)	0.0406 (12)	−0.0073 (10)	−0.0117 (10)	0.0002 (9)
C19	0.037 (3)	0.066 (5)	0.054 (4)	−0.012 (3)	−0.005 (2)	0.007 (3)
C20	0.051 (4)	0.082 (4)	0.083 (4)	−0.012 (3)	−0.013 (3)	−0.001 (3)
C21	0.088 (6)	0.156 (6)	0.080 (5)	−0.053 (4)	−0.022 (4)	0.025 (4)
C19A	0.039 (6)	0.047 (6)	0.059 (7)	−0.001 (5)	−0.009 (5)	0.004 (6)
C20A	0.049 (6)	0.090 (7)	0.091 (8)	−0.012 (5)	−0.012 (6)	0.009 (7)
C21A	0.066 (7)	0.134 (9)	0.099 (8)	−0.039 (6)	−0.037 (7)	−0.001 (6)
C22	0.0421 (14)	0.0560 (15)	0.0750 (19)	−0.0132 (12)	−0.0036 (13)	−0.0016 (14)
C23	0.0684 (19)	0.076 (2)	0.106 (2)	−0.0324 (16)	−0.0274 (18)	−0.0004 (18)
C24	0.0475 (14)	0.0577 (14)	0.0440 (13)	0.0017 (11)	−0.0181 (11)	−0.0066 (11)
C25	0.082 (2)	0.0597 (16)	0.0582 (16)	−0.0085 (14)	−0.0262 (14)	−0.0105 (13)
C26	0.083 (2)	0.090 (2)	0.0461 (15)	−0.0248 (17)	−0.0142 (14)	−0.0060 (14)
N1	0.0339 (9)	0.0341 (9)	0.0401 (9)	−0.0045 (7)	−0.0079 (8)	0.0038 (7)
N2	0.0362 (10)	0.0399 (10)	0.0519 (11)	−0.0051 (8)	−0.0049 (8)	0.0056 (9)
N3	0.0432 (11)	0.0488 (11)	0.0482 (11)	−0.0119 (9)	−0.0106 (9)	0.0017 (9)
S1	0.0500 (4)	0.0464 (4)	0.0679 (4)	−0.0117 (3)	−0.0092 (3)	0.0180 (3)
O1	0.0488 (10)	0.0606 (10)	0.0535 (10)	−0.0221 (8)	−0.0063 (8)	0.0031 (8)
O2	0.0786 (14)	0.0983 (16)	0.0796 (14)	−0.0437 (12)	0.0075 (11)	0.0099 (12)
C1'	0.0465 (14)	0.0403 (13)	0.0686 (16)	−0.0029 (11)	−0.0137 (12)	−0.0027 (11)
C2'	0.0510 (16)	0.0415 (14)	0.103 (2)	−0.0102 (12)	−0.0095 (15)	−0.0049 (14)
C3'	0.0719 (19)	0.0481 (16)	0.081 (2)	−0.0151 (14)	0.0111 (16)	0.0051 (15)
C4'	0.098 (2)	0.0552 (16)	0.0550 (16)	−0.0142 (16)	−0.0009 (15)	0.0055 (13)
C5'	0.0719 (18)	0.0496 (14)	0.0477 (14)	−0.0159 (13)	−0.0100 (12)	0.0041 (11)
C6'	0.0385 (12)	0.0332 (11)	0.0475 (13)	−0.0010 (9)	−0.0066 (10)	−0.0008 (9)
C7'	0.0386 (12)	0.0395 (12)	0.0406 (12)	−0.0016 (9)	−0.0112 (10)	0.0024 (9)
C8'	0.0409 (12)	0.0457 (13)	0.0456 (12)	−0.0117 (10)	−0.0191 (10)	0.0078 (10)
C9'	0.0489 (13)	0.0355 (11)	0.0422 (12)	−0.0136 (10)	−0.0163 (10)	0.0040 (9)
C10'	0.0425 (12)	0.0398 (12)	0.0432 (12)	−0.0039 (10)	−0.0122 (10)	−0.0062 (9)
C11'	0.0349 (11)	0.0360 (11)	0.0397 (11)	−0.0048 (9)	−0.0088 (9)	−0.0005 (9)
C12'	0.0367 (12)	0.0424 (12)	0.0350 (11)	−0.0028 (9)	−0.0089 (9)	−0.0026 (9)
C13'	0.0481 (14)	0.0465 (13)	0.0650 (15)	−0.0091 (11)	−0.0236 (12)	0.0052 (11)
C14'	0.0520 (16)	0.0669 (17)	0.0841 (19)	−0.0182 (13)	−0.0278 (14)	0.0013 (15)
C15'	0.0500 (15)	0.087 (2)	0.0677 (17)	−0.0101 (15)	−0.0309 (14)	0.0058 (15)
C16'	0.0554 (16)	0.0728 (18)	0.0589 (16)	−0.0044 (14)	−0.0223 (13)	0.0232 (14)
C17'	0.0439 (13)	0.0552 (14)	0.0501 (14)	−0.0078 (11)	−0.0123 (11)	0.0093 (11)
C18'	0.0393 (12)	0.0427 (12)	0.0438 (13)	−0.0063 (10)	−0.0095 (10)	−0.0013 (10)
C19'	0.0799 (19)	0.0606 (16)	0.0440 (14)	−0.0020 (14)	−0.0168 (13)	−0.0070 (12)
C20'	0.119 (3)	0.099 (3)	0.105 (3)	0.018 (3)	−0.064 (3)	−0.042 (2)
C21'	0.084 (4)	0.188 (6)	0.134 (6)	0.001 (4)	−0.034 (4)	−0.085 (5)
C21B	0.079 (14)	0.18 (2)	0.103 (19)	0.013 (13)	−0.059 (13)	−0.060 (15)
C22'	0.104 (2)	0.0535 (16)	0.0520 (16)	−0.0091 (16)	−0.0336 (17)	−0.0069 (13)
C23'	0.122 (3)	0.087 (2)	0.136 (3)	−0.003 (2)	−0.077 (3)	−0.047 (2)
C24'	0.0420 (13)	0.0625 (15)	0.0613 (15)	−0.0185 (12)	−0.0199 (12)	0.0140 (12)
C25'	0.0522 (18)	0.098 (2)	0.124 (3)	−0.0241 (17)	0.0116 (18)	−0.011 (2)
C26'	0.074 (2)	0.0738 (19)	0.097 (2)	−0.0384 (16)	−0.0282 (17)	0.0160 (17)
N1'	0.0372 (10)	0.0382 (10)	0.0376 (10)	−0.0009 (8)	−0.0109 (8)	−0.0029 (8)
N2'	0.0531 (12)	0.0440 (11)	0.0381 (10)	−0.0011 (9)	−0.0098 (9)	−0.0040 (9)
N3'	0.0611 (13)	0.0496 (11)	0.0488 (12)	−0.0132 (10)	−0.0211 (10)	−0.0031 (9)
S1'	0.0723 (5)	0.0507 (4)	0.0573 (4)	0.0123 (3)	−0.0119 (3)	−0.0111 (3)
O1'	0.0712 (12)	0.0580 (10)	0.0489 (9)	−0.0131 (9)	−0.0154 (9)	−0.0144 (8)
O2'	0.126 (2)	0.0888 (16)	0.0640 (13)	−0.0094 (14)	−0.0098 (13)	−0.0324 (12)

C1—C6	1.380 (3)	N2—H2A	0.866 (15)
C1—C2	1.381 (3)	N3—O1	1.444 (2)
C1—H1	0.9300	C1'—C6'	1.383 (3)
C2—C3	1.369 (4)	C1'—C2'	1.387 (3)
C2—H2	0.9300	C1'—H1'	0.9300
C3—C4	1.357 (4)	C2'—C3'	1.361 (4)
C3—H3	0.9300	C2'—H2'	0.9300
C4—C5	1.379 (3)	C3'—C4'	1.351 (4)
C4—H4	0.9300	C3'—H3'	0.9300
C5—C6	1.385 (3)	C4'—C5'	1.381 (3)
C5—H5	0.9300	C4'—H4'	0.9300
C6—C7	1.525 (3)	C5'—C6'	1.382 (3)
C7—N1	1.484 (2)	C5'—H5'	0.9300
C7—C8	1.527 (3)	C6'—C7'	1.521 (3)
C7—H7	0.9800	C7'—N1'	1.481 (3)
C8—C9	1.504 (3)	C7'—C8'	1.534 (3)
C8—C24	1.543 (3)	C7'—H7'	0.9800
C8—H8	0.9800	C8'—C9'	1.506 (3)
C9—N3	1.268 (3)	C8'—C24'	1.542 (3)
C9—C10	1.485 (3)	C8'—H8'	0.9800
C10—C11	1.532 (3)	C9'—N3'	1.271 (3)
C10—H10C	0.9700	C9'—C10'	1.486 (3)
C10—H10D	0.9700	C10'—C11'	1.523 (3)
C11—N1	1.486 (2)	C10'—H10A	0.9700
C11—C12	1.516 (3)	C10'—H10B	0.9700
C11—H11	0.9800	C11'—N1'	1.490 (3)
C12—C17	1.381 (3)	C11'—C12'	1.515 (3)
C12—C13	1.382 (3)	C11'—H11'	0.9800
C13—C14	1.380 (3)	C12'—C17'	1.376 (3)
C13—H13	0.9300	C12'—C13'	1.383 (3)
C14—C15	1.360 (4)	C13'—C14'	1.371 (3)
C14—H14	0.9300	C13'—H13'	0.9300
C15—C16	1.368 (4)	C14'—C15'	1.366 (4)
C15—H15	0.9300	C14'—H14'	0.9300
C16—C17	1.388 (3)	C15'—C16'	1.363 (4)
C16—H16	0.9300	C15'—H15'	0.9300
C17—H17	0.9300	C16'—C17'	1.381 (3)
C18—N2	1.335 (3)	C16'—H16'	0.9300
C18—N1	1.363 (2)	C17'—H17'	0.9300
C18—S1	1.687 (2)	C18'—N2'	1.338 (3)
C19—N2	1.455 (5)	C18'—N1'	1.367 (3)
C19—C20	1.490 (8)	C18'—S1'	1.685 (2)
C19—H19A	0.9700	C19'—N2'	1.445 (3)
C19—H19B	0.9700	C19'—C20'	1.459 (4)
C20—C21	1.238 (7)	C19'—H19E	0.9700
C20—H20A	0.9300	C19'—H19F	0.9700
C21—H21A	0.9300	C20'—C21'	1.192 (5)
C21—H21B	0.9300	C20'—C21B	1.216 (9)
C19A—N2	1.457 (7)	C20'—H20E	0.9300
C19A—C20A	1.495 (10)	C20'—H20F	0.9300
C19A—H19C	0.9700	C21'—H21E	0.9300
C19A—H19D	0.9700	C21'—H21F	0.9300
C20A—C21A	1.242 (9)	C21B—H21G	0.9300
C20A—H20C	0.9300	C21B—H21H	0.9300
C21A—H21C	0.9300	C22'—O2'	1.203 (3)
C21A—H21D	0.9300	C22'—O1'	1.355 (3)
C22—O2	1.194 (3)	C22'—C23'	1.483 (4)
C22—O1	1.355 (3)	C23'—H23D	0.9600
C22—C23	1.470 (4)	C23'—H23E	0.9600
C23—H23A	0.9600	C23'—H23F	0.9600
C23—H23B	0.9600	C24'—C25'	1.509 (4)
C23—H23C	0.9600	C24'—C26'	1.514 (4)
C24—C25	1.511 (3)	C24'—H24'	0.9800
C24—C26	1.520 (3)	C25'—H25D	0.9600
C24—H24	0.9800	C25'—H25E	0.9600
C25—H25A	0.9600	C25'—H25F	0.9600
C25—H25B	0.9600	C26'—H26D	0.9600
C25—H25C	0.9600	C26'—H26E	0.9600
C26—H26A	0.9600	C26'—H26F	0.9600
C26—H26B	0.9600	N2'—H2B	0.878 (16)
C26—H26C	0.9600	N3'—O1'	1.443 (3)
C6—C1—C2	120.9 (2)	C19—N2—H2A	114.8 (17)
C6—C1—H1	119.5	C19A—N2—H2A	113 (2)
C2—C1—H1	119.5	C9—N3—O1	110.22 (17)
C3—C2—C1	120.4 (3)	C22—O1—N3	113.05 (18)
C3—C2—H2	119.8	C6'—C1'—C2'	120.5 (3)
C1—C2—H2	119.8	C6'—C1'—H1'	119.7
C4—C3—C2	119.3 (3)	C2'—C1'—H1'	119.7
C4—C3—H3	120.3	C3'—C2'—C1'	120.4 (3)
C2—C3—H3	120.3	C3'—C2'—H2'	119.8
C3—C4—C5	120.9 (3)	C1'—C2'—H2'	119.8
C3—C4—H4	119.5	C4'—C3'—C2'	119.7 (3)
C5—C4—H4	119.5	C4'—C3'—H3'	120.1
C4—C5—C6	120.6 (2)	C2'—C3'—H3'	120.1
C4—C5—H5	119.7	C3'—C4'—C5'	120.8 (3)
C6—C5—H5	119.7	C3'—C4'—H4'	119.6
C1—C6—C5	117.8 (2)	C5'—C4'—H4'	119.6
C1—C6—C7	120.21 (19)	C4'—C5'—C6'	120.7 (3)
C5—C6—C7	121.8 (2)	C4'—C5'—H5'	119.7
N1—C7—C6	112.82 (17)	C6'—C5'—H5'	119.7
N1—C7—C8	109.01 (16)	C5'—C6'—C1'	117.9 (2)
C6—C7—C8	114.69 (17)	C5'—C6'—C7'	121.8 (2)
N1—C7—H7	106.6	C1'—C6'—C7'	120.1 (2)
C6—C7—H7	106.6	N1'—C7'—C6'	112.90 (17)
C8—C7—H7	106.6	N1'—C7'—C8'	108.90 (16)
C9—C8—C7	106.97 (17)	C6'—C7'—C8'	114.75 (17)
C9—C8—C24	112.95 (17)	N1'—C7'—H7'	106.6
C7—C8—C24	114.39 (17)	C6'—C7'—H7'	106.6
C9—C8—H8	107.4	C8'—C7'—H7'	106.6
C7—C8—H8	107.4	C9'—C8'—C7'	106.51 (17)
C24—C8—H8	107.4	C9'—C8'—C24'	114.19 (18)
N3—C9—C10	126.87 (19)	C7'—C8'—C24'	113.71 (19)
N3—C9—C8	116.60 (19)	C9'—C8'—H8'	107.4
C10—C9—C8	116.37 (17)	C7'—C8'—H8'	107.4
C9—C10—C11	113.67 (17)	C24'—C8'—H8'	107.4
C9—C10—H10C	108.8	N3'—C9'—C10'	126.9 (2)
C11—C10—H10C	108.8	N3'—C9'—C8'	116.2 (2)
C9—C10—H10D	108.8	C10'—C9'—C8'	116.81 (19)
C11—C10—H10D	108.8	C9'—C10'—C11'	113.53 (18)
H10C—C10—H10D	107.7	C9'—C10'—H10A	108.9
N1—C11—C12	113.53 (16)	C11'—C10'—H10A	108.9
N1—C11—C10	111.00 (16)	C9'—C10'—H10B	108.9
C12—C11—C10	109.06 (16)	C11'—C10'—H10B	108.9
N1—C11—H11	107.7	H10A—C10'—H10B	107.7
C12—C11—H11	107.7	N1'—C11'—C12'	113.42 (16)
C10—C11—H11	107.7	N1'—C11'—C10'	111.21 (16)
C17—C12—C13	119.0 (2)	C12'—C11'—C10'	109.08 (16)
C17—C12—C11	119.2 (2)	N1'—C11'—H11'	107.6
C13—C12—C11	121.78 (19)	C12'—C11'—H11'	107.6
C14—C13—C12	120.0 (2)	C10'—C11'—H11'	107.6
C14—C13—H13	120.0	C17'—C12'—C13'	118.3 (2)
C12—C13—H13	120.0	C17'—C12'—C11'	119.51 (19)
C15—C14—C13	120.9 (3)	C13'—C12'—C11'	122.16 (18)
C15—C14—H14	119.6	C14'—C13'—C12'	120.4 (2)
C13—C14—H14	119.6	C14'—C13'—H13'	119.8
C14—C15—C16	119.8 (2)	C12'—C13'—H13'	119.8
C14—C15—H15	120.1	C15'—C14'—C13'	120.8 (2)
C16—C15—H15	120.1	C15'—C14'—H14'	119.6
C15—C16—C17	120.2 (3)	C13'—C14'—H14'	119.6
C15—C16—H16	119.9	C16'—C15'—C14'	119.5 (2)
C17—C16—H16	119.9	C16'—C15'—H15'	120.3
C12—C17—C16	120.1 (2)	C14'—C15'—H15'	120.3
C12—C17—H17	120.0	C15'—C16'—C17'	120.3 (2)
C16—C17—H17	120.0	C15'—C16'—H16'	119.9
N2—C18—N1	117.20 (17)	C17'—C16'—H16'	119.9
N2—C18—S1	120.64 (16)	C12'—C17'—C16'	120.7 (2)
N1—C18—S1	122.16 (16)	C12'—C17'—H17'	119.6
N2—C19—C20	114.7 (7)	C16'—C17'—H17'	119.6
N2—C19—H19A	108.6	N2'—C18'—N1'	116.93 (19)
C20—C19—H19A	108.6	N2'—C18'—S1'	120.93 (17)
N2—C19—H19B	108.6	N1'—C18'—S1'	122.13 (16)
C20—C19—H19B	108.6	N2'—C19'—C20'	115.6 (3)
H19A—C19—H19B	107.6	N2'—C19'—H19E	108.4
C21—C20—C19	128.1 (9)	C20'—C19'—H19E	108.4
C21—C20—H20A	115.9	N2'—C19'—H19F	108.4
C19—C20—H20A	115.9	C20'—C19'—H19F	108.4
C20—C21—H21A	120.0	H19E—C19'—H19F	107.4
C20—C21—H21B	120.0	C21'—C20'—C19'	130.6 (5)
H21A—C21—H21B	120.0	C21B—C20'—C19'	157.3 (15)
N2—C19A—C20A	111.5 (10)	C21'—C20'—H20E	114.7
N2—C19A—H19C	109.3	C19'—C20'—H20E	114.7
C20A—C19A—H19C	109.3	C21B—C20'—H20F	101.3
N2—C19A—H19D	109.3	C19'—C20'—H20F	101.3
C20A—C19A—H19D	109.3	C20'—C21'—H21E	120.0
H19C—C19A—H19D	108.0	C20'—C21'—H21F	120.0
C21A—C20A—C19A	126.9 (17)	H21E—C21'—H21F	120.0
C21A—C20A—H20C	116.6	C20'—C21B—H21G	120.0
C19A—C20A—H20C	116.6	C20'—C21B—H21H	120.0
C20A—C21A—H21C	120.0	H21G—C21B—H21H	120.0
C20A—C21A—H21D	120.0	O2'—C22'—O1'	116.2 (3)
H21C—C21A—H21D	120.0	O2'—C22'—C23'	126.3 (3)
O2—C22—O1	116.7 (3)	O1'—C22'—C23'	117.4 (3)
O2—C22—C23	125.3 (2)	C22'—C23'—H23D	109.5
O1—C22—C23	118.0 (2)	C22'—C23'—H23E	109.5
C22—C23—H23A	109.5	H23D—C23'—H23E	109.5
C22—C23—H23B	109.5	C22'—C23'—H23F	109.5
H23A—C23—H23B	109.5	H23D—C23'—H23F	109.5
C22—C23—H23C	109.5	H23E—C23'—H23F	109.5
H23A—C23—H23C	109.5	C25'—C24'—C26'	110.1 (2)
H23B—C23—H23C	109.5	C25'—C24'—C8'	110.5 (2)
C25—C24—C26	110.5 (2)	C26'—C24'—C8'	111.3 (2)
C25—C24—C8	110.79 (19)	C25'—C24'—H24'	108.3
C26—C24—C8	111.3 (2)	C26'—C24'—H24'	108.3
C25—C24—H24	108.0	C8'—C24'—H24'	108.3
C26—C24—H24	108.0	C24'—C25'—H25D	109.5
C8—C24—H24	108.0	C24'—C25'—H25E	109.5
C24—C25—H25A	109.5	H25D—C25'—H25E	109.5
C24—C25—H25B	109.5	C24'—C25'—H25F	109.5
H25A—C25—H25B	109.5	H25D—C25'—H25F	109.5
C24—C25—H25C	109.5	H25E—C25'—H25F	109.5
H25A—C25—H25C	109.5	C24'—C26'—H26D	109.5
H25B—C25—H25C	109.5	C24'—C26'—H26E	109.5
C24—C26—H26A	109.5	H26D—C26'—H26E	109.5
C24—C26—H26B	109.5	C24'—C26'—H26F	109.5
H26A—C26—H26B	109.5	H26D—C26'—H26F	109.5
C24—C26—H26C	109.5	H26E—C26'—H26F	109.5
H26A—C26—H26C	109.5	C18'—N1'—C7'	118.81 (17)
H26B—C26—H26C	109.5	C18'—N1'—C11'	121.76 (16)
C18—N1—C7	118.77 (16)	C7'—N1'—C11'	116.86 (16)
C18—N1—C11	121.97 (16)	C18'—N2'—C19'	125.3 (2)
C7—N1—C11	116.89 (15)	C18'—N2'—H2B	121.5 (16)
C18—N2—C19	125.1 (8)	C19'—N2'—H2B	112.1 (16)
C18—N2—C19A	125.4 (13)	C9'—N3'—O1'	110.08 (18)
C18—N2—H2A	120.1 (16)	C22'—O1'—N3'	113.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2i	0.93	2.59	3.298 (4)	133
C2′—H2′···O2′ii	0.93	2.59	3.332 (4)	137

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C2H2O2i	0.93	2.59	3.298(4)	133
C2H2O2ii	0.93	2.59	3.332(4)	137

Symmetry codes: (i) ; (ii) .