A phase transition from monoclinic C2 with Z′ = 1 to triclinic P1 with Z′ = 4 for the quasiracemate L-2-amino­butyric acid–D-me­thio­nine (1/1)

Racemates of hydro­phobic amino acids with linear side chains are known to undergo a unique series of solid-state phase transitions that involve sliding of mol­ecular bilayers upon heating or cooling. Recently, this behaviour was shown to extend also to quasiracemates of two different amino acids with opposite handedness [Görbitz & Karen (2015). J. Phys. Chem. B, 119, 4975–4984]. Previous investigations are here extended to an L-2-amino­butyric acid–D-me­thio­nine (1/1) co-crystal, C₄H₉NO₂·C₅H₁₁NO₂S. The significant difference in size between the –CH₂CH₃ and –CH₂CH₂SCH₃ side chains leads to extensive disorder at room temperature, which is essentially resolved after a phase transition at 229 K to an unprecedented triclinic form where all four D-me­thio­­nine mol­ecules in the asymmetric unit have different side-chain conformations and all three side-chain rotamers are used for the four partner L-2-amino­butyric acid mol­ecules.

Computing details

For both compounds, data collection: APEX2 (Bruker, 2014); cell refinement: APEX2 (Bruker, 2014); data reduction: APEX2 (Bruker, 2014); program(s) used to solve structure: APEX2 (Bruker, 2014); program(s) used to refine structure: SHELXT (Sheldrick, 2015a); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

(103) (S)-2-Aminobutanoic acid–(R)-2-amino-4-(methylsulfanyl)butanoic acid (1/1)

Crystal data

C4H9NO2·C5H11NO2S	Z = 4
Mr = 252.33	F(000) = 544
Triclinic, P1	Dx = 1.295 Mg m^−3
a = 9.4890 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8774 (15) Å	Cell parameters from 6485 reflections
c = 15.079 (2) Å	θ = 3.0–50.1°
α = 71.429 (4)°	µ = 0.25 mm^−1
β = 75.650 (4)°	T = 103 K
γ = 89.369 (4)°	Plate, colorless
V = 1294.4 (4) Å^3	0.69 × 0.65 × 0.10 mm

Data collection

Bruker D8 Venture with Photon 100 CMOS detector diffractometer	4175 independent reflections
Radiation source: fine-focus sealed tube	3442 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
Detector resolution: 8.3 pixels mm^-1	θmax = 25.2°, θmin = 2.2°
Sets of exposures each taken over 0.5° ω rotation scans	h = −10→11
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −10→11
Tmin = 0.888, Tmax = 1.000	l = 0→18
4175 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.072	w = 1/[σ^2(Fo^2) + (0.1022P)^2 + 1.242P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.186	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.43 e Å^−3
4175 reflections	Δρmin = −0.45 e Å^−3
628 parameters	Absolute structure: No quotients, so Flack parameter determined by classical intensity fit
461 restraints	Absolute structure parameter: 0.18 (12)

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.

Refinement. The final refinement was done against the HKLF 5 type file for twin component 1 with intensities corrected for overlap with component 2.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1E	0.4882 (8)	0.7762 (9)	0.4273 (6)	0.0217 (15)
O2E	0.6454 (9)	0.9697 (9)	0.3503 (6)	0.0254 (16)
N1E	0.6829 (10)	0.5925 (10)	0.3894 (6)	0.0187 (18)
H1E	0.6025	0.5605	0.3771	0.028*
H2E	0.6637	0.5839	0.4532	0.028*
H3E	0.7587	0.5396	0.3744	0.028*
C1E	0.6080 (12)	0.8369 (12)	0.3740 (8)	0.022 (2)
C21E	0.722 (4)	0.746 (5)	0.3294 (12)	0.016 (3)	0.650 (19)
H21E	0.8232	0.7765	0.3270	0.020*	0.650 (19)
C31E	0.706 (2)	0.7613 (18)	0.2269 (11)	0.018 (4)	0.650 (19)
H31E	0.7729	0.6987	0.1996	0.022*	0.650 (19)
H32E	0.6051	0.7294	0.2317	0.022*	0.650 (19)
C41E	0.7402 (17)	0.9146 (16)	0.1596 (11)	0.024 (4)	0.650 (19)
H41E	0.7594	0.9163	0.0924	0.036*	0.650 (19)
H42E	0.8265	0.9559	0.1692	0.036*	0.650 (19)
H43E	0.6569	0.9708	0.1738	0.036*	0.650 (19)
C22E	0.709 (7)	0.746 (8)	0.3413 (19)	0.016 (3)	0.350 (19)
H22E	0.7995	0.7704	0.3579	0.020*	0.350 (19)
C32E	0.760 (3)	0.776 (4)	0.2306 (18)	0.018 (4)	0.350 (19)
H33E	0.8165	0.8701	0.1995	0.022*	0.350 (19)
H34E	0.8247	0.7018	0.2173	0.022*	0.350 (19)
C42E	0.632 (3)	0.776 (3)	0.187 (2)	0.032 (9)	0.350 (19)
H44E	0.6679	0.7910	0.1179	0.049*	0.350 (19)
H45E	0.5708	0.8540	0.1966	0.049*	0.350 (19)
H46E	0.5738	0.6845	0.2193	0.049*	0.350 (19)
O1G	−0.0238 (8)	0.7764 (9)	0.4295 (5)	0.0199 (15)
O2G	0.1385 (9)	0.9672 (9)	0.3650 (6)	0.0241 (16)
N1G	0.1730 (10)	0.5925 (10)	0.3956 (6)	0.0169 (17)
H1G	0.0927	0.5744	0.3772	0.025*
H2G	0.1505	0.5692	0.4612	0.025*
H3G	0.2457	0.5394	0.3761	0.025*
C1G	0.0984 (11)	0.8378 (12)	0.3845 (8)	0.016 (2)
C21G	0.223 (3)	0.749 (3)	0.3497 (10)	0.013 (3)	0.655 (16)
H21G	0.3082	0.7673	0.3729	0.015*	0.655 (16)
C31G	0.2710 (16)	0.7912 (18)	0.2389 (10)	0.020 (3)	0.655 (16)
H31G	0.3371	0.7200	0.2217	0.024*	0.655 (16)
H32G	0.3280	0.8850	0.2130	0.024*	0.655 (16)
C41G	0.1474 (18)	0.801 (2)	0.1884 (12)	0.038 (5)	0.655 (16)
H41G	0.1891	0.8205	0.1189	0.057*	0.655 (16)
H42G	0.0876	0.8795	0.1983	0.057*	0.655 (16)
H43G	0.0867	0.7109	0.2157	0.057*	0.655 (16)
C22G	0.204 (6)	0.742 (5)	0.3380 (16)	0.013 (3)	0.345 (16)
H22G	0.3059	0.7702	0.3361	0.015*	0.345 (16)
C32G	0.198 (4)	0.763 (2)	0.2337 (17)	0.020 (3)	0.345 (16)
H33G	0.0982	0.7322	0.2351	0.024*	0.345 (16)
H34G	0.2657	0.6996	0.2081	0.024*	0.345 (16)
C42G	0.236 (4)	0.917 (3)	0.163 (2)	0.041*	0.345 (16)
H44G	0.2552	0.9158	0.0965	0.062*	0.345 (16)
H45G	0.3230	0.9574	0.1724	0.062*	0.345 (16)
H46G	0.1541	0.9753	0.1758	0.062*	0.345 (16)
O1B	0.7309 (8)	0.0760 (9)	0.5794 (5)	0.0193 (15)
O2B	0.5663 (9)	−0.1107 (9)	0.6611 (5)	0.0206 (15)
N1B	0.5415 (10)	0.2694 (10)	0.6085 (6)	0.0180 (18)
H1B	0.5610	0.2727	0.5456	0.027*
H2B	0.6207	0.3072	0.6188	0.027*
H3B	0.4636	0.3209	0.6217	0.027*
C1B	0.6101 (11)	0.0203 (11)	0.6330 (7)	0.015 (2)
C21B	0.5069 (18)	0.1143 (18)	0.6746 (9)	0.012 (3)	0.832 (16)
H21B	0.4033	0.0821	0.6834	0.015*	0.832 (16)
C31B	0.5322 (14)	0.1196 (13)	0.7718 (9)	0.022 (3)	0.832 (16)
H31B	0.6369	0.1447	0.7621	0.026*	0.832 (16)
H32B	0.4762	0.1957	0.7904	0.026*	0.832 (16)
C41B	0.4870 (15)	−0.0208 (14)	0.8529 (9)	0.028 (3)	0.832 (16)
H41B	0.5204	−0.1000	0.8278	0.034*	0.832 (16)
H42B	0.3792	−0.0323	0.8748	0.034*	0.832 (16)
S11B	0.5587 (10)	−0.0350 (10)	0.9551 (6)	0.0320 (13)	0.832 (16)
C22B	0.496 (7)	0.142 (10)	0.672 (3)	0.012 (3)	0.168 (16)
H22B	0.4009	0.1208	0.6606	0.015*	0.168 (16)
C32B	0.471 (4)	0.072 (6)	0.784 (2)	0.022 (3)	0.168 (16)
H33B	0.4100	0.1324	0.8171	0.026*	0.168 (16)
H34B	0.4162	−0.0227	0.8047	0.026*	0.168 (16)
C42B	0.611 (3)	0.052 (7)	0.815 (2)	0.028*	0.168 (16)
H43B	0.6721	0.1438	0.7854	0.034*	0.168 (16)
H44B	0.6653	−0.0196	0.7889	0.034*	0.168 (16)
S12B	0.586 (4)	−0.006 (4)	0.944 (2)	0.0320 (13)	0.168 (16)
C5B	0.4806 (19)	0.1149 (18)	0.9896 (12)	0.070 (4)
H51B	0.5421	0.2029	0.9499	0.105*
H52B	0.4752	0.0981	1.0581	0.105*
H53B	0.3824	0.1249	0.9795	0.105*
O1C	0.1618 (9)	0.5833 (9)	0.5859 (5)	0.0187 (15)
O2C	0.2785 (9)	0.3947 (9)	0.6496 (5)	0.0218 (15)
N1C	0.3431 (10)	0.7672 (10)	0.6111 (6)	0.0172 (18)
H1C	0.3786	0.7749	0.5477	0.026*
H2C	0.4045	0.8184	0.6283	0.026*
H3C	0.2533	0.8020	0.6199	0.026*
C1C	0.2529 (11)	0.5241 (11)	0.6314 (7)	0.017 (2)
C21C	0.3315 (12)	0.6130 (11)	0.6725 (7)	0.016 (2)	0.936 (19)
H21C	0.4318	0.5802	0.6714	0.019*	0.936 (19)
C31C	0.2519 (14)	0.6019 (17)	0.7758 (8)	0.025 (3)	0.936 (19)
H31C	0.3024	0.6698	0.7959	0.029*	0.936 (19)
H32C	0.1518	0.6319	0.7767	0.029*	0.936 (19)
C41C	0.2423 (17)	0.4538 (14)	0.8491 (9)	0.046 (4)	0.936 (19)
H41C	0.1728	0.3906	0.8395	0.069*	0.936 (19)
H42C	0.2093	0.4595	0.9147	0.069*	0.936 (19)
H43C	0.3386	0.4154	0.8406	0.069*	0.936 (19)
C22C	0.3315 (12)	0.6130 (11)	0.6725 (7)	0.016 (2)	0.064 (19)
H22C	0.4342	0.5851	0.6584	0.019*	0.064 (19)
C32C	0.295 (7)	0.60 (2)	0.780 (3)	0.025 (3)	0.064 (19)
H33C	0.3525	0.5201	0.8116	0.029*	0.064 (19)
H34C	0.3269	0.6867	0.7868	0.029*	0.064 (19)
C42C	0.135 (8)	0.56 (2)	0.832 (4)	0.043*	0.064 (19)
H44C	0.1167	0.5768	0.8944	0.065*	0.064 (19)
H45C	0.1103	0.4584	0.8433	0.065*	0.064 (19)
H46C	0.0760	0.6196	0.7926	0.065*	0.064 (19)
O1A	0.6717 (9)	0.5869 (9)	0.5775 (5)	0.0223 (16)
O2A	0.7779 (9)	0.3929 (9)	0.6481 (6)	0.0253 (17)
N1A	0.8362 (10)	0.7636 (10)	0.6190 (6)	0.0182 (18)
H1A	0.8781	0.7730	0.5559	0.027*
H2A	0.8933	0.8132	0.6402	0.027*
H3A	0.7466	0.7986	0.6244	0.027*
C1A	0.7533 (11)	0.5238 (11)	0.6283 (7)	0.015 (2)
C2A	0.8209 (12)	0.6072 (11)	0.6795 (7)	0.015 (2)
H21A	0.9196	0.5737	0.6838	0.018*
C3A	0.7253 (12)	0.5865 (12)	0.7813 (7)	0.020 (2)
H31A	0.6277	0.6187	0.7759	0.025*
H32A	0.7127	0.4828	0.8183	0.025*
C4A	0.7816 (14)	0.6632 (14)	0.8375 (8)	0.033 (3)
H41A	0.8633	0.6143	0.8593	0.050*
H42A	0.7036	0.6638	0.8938	0.050*
H43A	0.8148	0.7619	0.7962	0.050*
O1D	0.2394 (8)	0.0842 (9)	0.5821 (5)	0.0199 (15)
O2D	0.0771 (9)	−0.1056 (9)	0.6484 (6)	0.0235 (16)
N1D	0.0419 (10)	0.2701 (10)	0.6116 (6)	0.0174 (18)
H1D	0.1266	0.2935	0.6231	0.026*
H2D	−0.0295	0.3230	0.6332	0.026*
H3D	0.0549	0.2887	0.5469	0.026*
C1D	0.1136 (11)	0.0239 (11)	0.6276 (7)	0.017 (2)
C2D	−0.0015 (11)	0.1146 (11)	0.6635 (7)	0.015 (2)
H21D	−0.0939	0.0912	0.6491	0.018*
C3D	−0.0319 (12)	0.0811 (12)	0.7747 (8)	0.023 (2)
H3D1	−0.0917	0.1553	0.7932	0.028*
H3D2	−0.0895	−0.0122	0.8078	0.028*
C4D	0.1018 (12)	0.0757 (12)	0.8090 (7)	0.018 (2)
H41D	0.1563	0.1709	0.7792	0.021*
H42D	0.1645	0.0059	0.7869	0.021*
S1D	0.0656 (6)	0.0256 (7)	0.9401 (3)	0.0325 (7)
C5D	0.0043 (15)	−0.1595 (13)	0.9737 (9)	0.045 (3)
H51D	−0.0163	−0.2035	1.0442	0.067*
H52D	0.0804	−0.2095	0.9423	0.067*
H53D	−0.0846	−0.1666	0.9530	0.067*
O1F	1.0361 (8)	0.2797 (9)	0.4270 (5)	0.0188 (15)
O2F	0.9497 (9)	0.4753 (9)	0.3402 (5)	0.0191 (15)
N1F	0.8716 (10)	0.0993 (10)	0.3897 (6)	0.0204 (19)
H1F	0.8202	0.0452	0.3678	0.031*
H2F	0.8223	0.0955	0.4505	0.031*
H3F	0.9607	0.0647	0.3907	0.031*
C1F	0.9638 (11)	0.3423 (12)	0.3695 (7)	0.014 (2)
C2F	0.8907 (11)	0.2522 (11)	0.3233 (7)	0.014 (2)
H21F	0.7935	0.2878	0.3168	0.017*
C3F	0.9860 (13)	0.2558 (12)	0.2243 (7)	0.025 (2)
H31F	0.9476	0.1799	0.2048	0.030*
H32F	1.0864	0.2350	0.2296	0.030*
C4F	0.9907 (12)	0.4011 (13)	0.1457 (8)	0.030 (2)
H41F	1.0681	0.4030	0.0875	0.036*
H42F	1.0192	0.4770	0.1691	0.036*
S1F	0.8245 (6)	0.4444 (7)	0.1104 (3)	0.0323 (7)
C5F	0.8195 (14)	0.3254 (15)	0.0423 (10)	0.043 (3)
H51F	0.7314	0.3377	0.0185	0.065*
H52F	0.8184	0.2261	0.0840	0.065*
H53F	0.9059	0.3474	−0.0128	0.065*
O1H	0.5591 (9)	0.2715 (9)	0.4217 (5)	0.0199 (15)
O2H	0.4370 (9)	0.4621 (9)	0.3640 (5)	0.0199 (15)
N1H	0.3774 (10)	0.0867 (10)	0.3991 (6)	0.0181 (18)
H1H	0.3123	0.0346	0.3854	0.027*
H2H	0.3545	0.0712	0.4640	0.027*
H3H	0.4689	0.0596	0.3798	0.027*
C1H	0.4635 (12)	0.3306 (12)	0.3809 (7)	0.015 (2)
C2H	0.3720 (12)	0.2416 (12)	0.3469 (7)	0.016 (2)
H21H	0.2685	0.2667	0.3634	0.020*
C3H	0.4209 (12)	0.2687 (11)	0.2378 (7)	0.018 (2)
H31H	0.5268	0.2569	0.2192	0.022*
H32H	0.3696	0.1962	0.2220	0.022*
C4H	0.3910 (13)	0.4173 (12)	0.1788 (7)	0.021 (2)
H41H	0.4578	0.4897	0.1832	0.025*
H42H	0.2896	0.4371	0.2056	0.025*
S1H	0.4164 (6)	0.4304 (7)	0.0537 (3)	0.0288 (6)
C5H	0.3796 (15)	0.6137 (14)	0.0066 (9)	0.044 (3)
H51H	0.4409	0.6738	0.0250	0.066*
H52H	0.2766	0.6251	0.0331	0.066*
H53H	0.4012	0.6427	−0.0641	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1E	0.016 (4)	0.017 (4)	0.033 (4)	0.001 (3)	−0.004 (3)	−0.011 (3)
O2E	0.026 (4)	0.013 (4)	0.038 (4)	0.006 (3)	−0.010 (3)	−0.008 (3)
N1E	0.018 (4)	0.013 (4)	0.026 (4)	0.005 (3)	−0.008 (3)	−0.005 (3)
C1E	0.020 (5)	0.020 (5)	0.027 (5)	0.007 (4)	−0.007 (4)	−0.006 (4)
C21E	0.015 (5)	0.012 (4)	0.019 (4)	0.005 (4)	−0.002 (4)	−0.003 (4)
C31E	0.014 (6)	0.018 (5)	0.023 (4)	0.002 (5)	−0.004 (4)	−0.008 (4)
C41E	0.025 (8)	0.018 (8)	0.021 (7)	0.005 (6)	−0.005 (6)	0.003 (6)
C22E	0.015 (5)	0.012 (4)	0.019 (4)	0.005 (4)	−0.002 (4)	−0.003 (4)
C32E	0.014 (6)	0.018 (5)	0.023 (4)	0.002 (5)	−0.004 (4)	−0.008 (4)
C42E	0.028 (13)	0.028 (13)	0.037 (13)	0.003 (10)	0.005 (10)	−0.014 (10)
O1G	0.017 (4)	0.013 (3)	0.028 (4)	0.004 (3)	−0.003 (3)	−0.008 (3)
O2G	0.023 (4)	0.012 (4)	0.039 (4)	0.002 (3)	−0.011 (3)	−0.008 (3)
N1G	0.018 (4)	0.011 (4)	0.023 (4)	0.004 (3)	−0.006 (3)	−0.006 (3)
C1G	0.012 (4)	0.016 (4)	0.026 (4)	0.001 (3)	−0.011 (4)	−0.010 (4)
C21G	0.016 (6)	0.007 (4)	0.015 (4)	−0.001 (4)	−0.006 (4)	0.000 (4)
C31G	0.022 (6)	0.020 (5)	0.019 (5)	0.003 (4)	−0.004 (4)	−0.007 (4)
C41G	0.036 (9)	0.037 (9)	0.029 (8)	0.000 (7)	0.003 (7)	−0.004 (7)
C22G	0.016 (6)	0.007 (4)	0.015 (4)	−0.001 (4)	−0.006 (4)	0.000 (4)
C32G	0.022 (6)	0.020 (5)	0.019 (5)	0.003 (4)	−0.004 (4)	−0.007 (4)
O1B	0.011 (3)	0.024 (4)	0.022 (3)	0.007 (3)	−0.003 (3)	−0.006 (3)
O2B	0.019 (3)	0.013 (3)	0.034 (4)	0.002 (3)	−0.013 (3)	−0.009 (3)
N1B	0.021 (4)	0.016 (4)	0.020 (4)	−0.002 (3)	−0.005 (3)	−0.011 (3)
C1B	0.016 (4)	0.012 (4)	0.014 (4)	0.005 (3)	−0.003 (3)	−0.002 (3)
C21B	0.008 (4)	0.010 (6)	0.017 (4)	0.001 (4)	−0.005 (3)	0.000 (3)
C31B	0.019 (5)	0.017 (5)	0.030 (5)	−0.003 (4)	−0.009 (4)	−0.007 (4)
C41B	0.035 (6)	0.020 (5)	0.029 (5)	0.003 (4)	−0.007 (5)	−0.006 (4)
S11B	0.040 (3)	0.024 (3)	0.0316 (19)	0.002 (2)	−0.0156 (19)	−0.0039 (17)
C22B	0.008 (4)	0.010 (6)	0.017 (4)	0.001 (4)	−0.005 (3)	0.000 (3)
C32B	0.019 (5)	0.017 (5)	0.030 (5)	−0.003 (4)	−0.009 (4)	−0.007 (4)
S12B	0.040 (3)	0.024 (3)	0.0316 (19)	0.002 (2)	−0.0156 (19)	−0.0039 (17)
C5B	0.087 (7)	0.069 (7)	0.065 (7)	0.015 (6)	−0.027 (6)	−0.029 (5)
O1C	0.021 (3)	0.012 (3)	0.026 (4)	0.005 (3)	−0.010 (3)	−0.007 (3)
O2C	0.019 (3)	0.014 (3)	0.031 (4)	0.001 (3)	−0.004 (3)	−0.008 (3)
N1C	0.015 (4)	0.016 (4)	0.018 (4)	0.002 (3)	−0.004 (3)	−0.002 (3)
C1C	0.011 (4)	0.014 (4)	0.022 (4)	0.001 (3)	0.000 (3)	−0.003 (3)
C21C	0.014 (4)	0.012 (4)	0.020 (4)	0.002 (3)	−0.005 (3)	−0.002 (3)
C31C	0.028 (5)	0.021 (4)	0.025 (4)	0.002 (4)	−0.007 (3)	−0.007 (3)
C41C	0.074 (9)	0.024 (7)	0.034 (7)	−0.006 (6)	−0.013 (6)	0.001 (5)
C22C	0.014 (4)	0.012 (4)	0.020 (4)	0.002 (3)	−0.005 (3)	−0.002 (3)
C32C	0.028 (5)	0.021 (4)	0.025 (4)	0.002 (4)	−0.007 (3)	−0.007 (3)
O1A	0.025 (4)	0.025 (4)	0.018 (3)	0.003 (3)	−0.010 (3)	−0.006 (3)
O2A	0.020 (4)	0.012 (4)	0.046 (4)	0.001 (3)	−0.010 (3)	−0.011 (3)
N1A	0.019 (4)	0.007 (4)	0.026 (4)	−0.003 (3)	−0.005 (4)	−0.003 (3)
C1A	0.012 (4)	0.012 (4)	0.021 (4)	−0.001 (3)	−0.001 (3)	−0.007 (3)
C2A	0.014 (4)	0.009 (4)	0.022 (4)	0.000 (3)	−0.008 (4)	−0.001 (3)
C3A	0.015 (4)	0.017 (4)	0.025 (4)	0.004 (4)	−0.004 (4)	−0.001 (3)
C4A	0.043 (6)	0.035 (6)	0.027 (5)	0.001 (5)	−0.018 (5)	−0.012 (5)
O1D	0.015 (3)	0.017 (3)	0.023 (4)	0.002 (3)	−0.003 (3)	−0.003 (3)
O2D	0.024 (4)	0.010 (3)	0.039 (4)	0.003 (3)	−0.010 (3)	−0.010 (3)
N1D	0.021 (4)	0.008 (4)	0.023 (4)	0.002 (3)	−0.008 (3)	−0.003 (3)
C1D	0.018 (4)	0.013 (4)	0.019 (4)	0.003 (3)	−0.012 (4)	0.000 (3)
C2D	0.015 (4)	0.012 (4)	0.018 (4)	−0.004 (3)	−0.002 (3)	−0.004 (3)
C3D	0.028 (5)	0.014 (4)	0.021 (4)	−0.001 (4)	−0.002 (4)	0.001 (4)
C4D	0.027 (5)	0.017 (4)	0.007 (4)	0.007 (4)	−0.006 (4)	−0.001 (3)
S1D	0.0380 (16)	0.0353 (16)	0.0233 (14)	0.0049 (13)	−0.0100 (13)	−0.0068 (12)
C5D	0.052 (7)	0.032 (6)	0.029 (6)	0.017 (5)	0.004 (5)	0.006 (5)
O1F	0.012 (3)	0.017 (3)	0.026 (4)	0.000 (3)	−0.005 (3)	−0.005 (3)
O2F	0.020 (4)	0.009 (3)	0.033 (4)	0.004 (3)	−0.013 (3)	−0.008 (3)
N1F	0.010 (4)	0.014 (4)	0.033 (4)	0.003 (3)	−0.003 (3)	−0.003 (3)
C1F	0.010 (4)	0.016 (4)	0.018 (4)	0.000 (3)	−0.001 (3)	−0.011 (3)
C2F	0.011 (4)	0.010 (4)	0.020 (4)	−0.001 (3)	−0.010 (3)	0.000 (3)
C3F	0.024 (5)	0.019 (5)	0.028 (4)	0.001 (4)	−0.005 (4)	−0.003 (4)
C4F	0.027 (5)	0.022 (5)	0.033 (5)	0.000 (4)	−0.004 (4)	−0.001 (4)
S1F	0.0382 (16)	0.0249 (14)	0.0317 (14)	0.0074 (12)	−0.0127 (13)	−0.0039 (11)
C5F	0.041 (6)	0.038 (6)	0.061 (7)	0.006 (5)	−0.025 (6)	−0.022 (5)
O1H	0.020 (4)	0.016 (3)	0.028 (4)	0.000 (3)	−0.011 (3)	−0.009 (3)
O2H	0.019 (4)	0.012 (4)	0.031 (4)	0.005 (3)	−0.007 (3)	−0.010 (3)
N1H	0.017 (4)	0.011 (4)	0.029 (4)	0.002 (3)	−0.009 (3)	−0.008 (3)
C1H	0.014 (4)	0.012 (4)	0.020 (4)	0.001 (3)	−0.005 (4)	−0.006 (3)
C2H	0.016 (4)	0.009 (4)	0.019 (4)	0.002 (3)	0.001 (3)	−0.002 (3)
C3H	0.023 (5)	0.014 (4)	0.019 (4)	0.001 (4)	−0.007 (4)	−0.009 (3)
C4H	0.033 (5)	0.014 (4)	0.014 (4)	0.003 (4)	−0.008 (4)	−0.003 (3)
S1H	0.0378 (16)	0.0232 (14)	0.0241 (13)	0.0045 (11)	−0.0096 (12)	−0.0045 (11)
C5H	0.048 (7)	0.044 (7)	0.031 (6)	0.005 (5)	−0.013 (5)	0.001 (5)

Geometric parameters (Å, º)

O1E—C1E	1.246 (12)	C21C—C31C	1.522 (14)
O2E—C1E	1.274 (12)	C21C—H21C	1.0000
N1E—C22E	1.45 (8)	C31C—C41C	1.515 (17)
N1E—C21E	1.49 (4)	C31C—H31C	0.9900
N1E—H1E	0.9100	C31C—H32C	0.9900
N1E—H2E	0.9100	C41C—H41C	0.9800
N1E—H3E	0.9100	C41C—H42C	0.9800
C1E—C22E	1.41 (6)	C41C—H43C	0.9800
C1E—C21E	1.56 (3)	C32C—C42C	1.515 (17)
C21E—C31E	1.549 (18)	C32C—H33C	0.9900
C21E—H21E	1.0000	C32C—H34C	0.9900
C31E—C41E	1.516 (18)	C42C—H44C	0.9800
C31E—H31E	0.9900	C42C—H45C	0.9800
C31E—H32E	0.9900	C42C—H46C	0.9800
C41E—H41E	0.9800	O1A—C1A	1.247 (11)
C41E—H42E	0.9800	O2A—C1A	1.263 (10)
C41E—H43E	0.9800	N1A—C2A	1.510 (11)
C22E—C32E	1.548 (18)	N1A—H1A	0.9100
C22E—H22E	1.0000	N1A—H2A	0.9100
C32E—C42E	1.515 (18)	N1A—H3A	0.9100
C32E—H33E	0.9900	C1A—C2A	1.533 (13)
C32E—H34E	0.9900	C2A—C3A	1.528 (14)
C42E—H44E	0.9800	C2A—H21A	1.0000
C42E—H45E	0.9800	C3A—C4A	1.490 (15)
C42E—H46E	0.9800	C3A—H31A	0.9900
O1G—C1G	1.240 (11)	C3A—H32A	0.9900
O2G—C1G	1.257 (11)	C4A—H41A	0.9800
N1G—C22G	1.44 (4)	C4A—H42A	0.9800
N1G—C21G	1.51 (2)	C4A—H43A	0.9800
N1G—H1G	0.9100	O1D—C1D	1.264 (11)
N1G—H2G	0.9100	O2D—C1D	1.247 (11)
N1G—H3G	0.9100	N1D—C2D	1.494 (11)
C1G—C21G	1.55 (3)	N1D—H1D	0.9100
C1G—C22G	1.57 (5)	N1D—H2D	0.9100
C21G—C31G	1.535 (16)	N1D—H3D	0.9100
C21G—H21G	1.0000	C1D—C2D	1.511 (13)
C31G—C41G	1.536 (19)	C2D—C3D	1.553 (13)
C31G—H31G	0.9900	C2D—H21D	1.0000
C31G—H32G	0.9900	C3D—C4D	1.478 (14)
C41G—H41G	0.9800	C3D—H3D1	0.9900
C41G—H42G	0.9800	C3D—H3D2	0.9900
C41G—H43G	0.9800	C4D—S1D	1.821 (9)
C22G—C32G	1.535 (16)	C4D—H41D	0.9900
C22G—H22G	1.0000	C4D—H42D	0.9900
C32G—C42G	1.535 (19)	S1D—C5D	1.796 (12)
C32G—H33G	0.9900	C5D—H51D	0.9800
C32G—H34G	0.9900	C5D—H52D	0.9800
C42G—H44G	0.9800	C5D—H53D	0.9800
C42G—H45G	0.9800	O1F—C1F	1.244 (11)
C42G—H46G	0.9800	O2F—C1F	1.263 (11)
O1B—C1B	1.241 (11)	N1F—C2F	1.506 (11)
O2B—C1B	1.265 (11)	N1F—H1F	0.9100
N1B—C22B	1.31 (8)	N1F—H2F	0.9100
N1B—C21B	1.524 (16)	N1F—H3F	0.9100
N1B—H1B	0.9100	C1F—C2F	1.551 (13)
N1B—H2B	0.9100	C2F—C3F	1.532 (14)
N1B—H3B	0.9100	C2F—H21F	1.0000
C1B—C21B	1.503 (16)	C3F—C4F	1.536 (13)
C1B—C22B	1.76 (9)	C3F—H31F	0.9900
C21B—C31B	1.560 (16)	C3F—H32F	0.9900
C21B—H21B	1.0000	C4F—S1F	1.791 (11)
C31B—C41B	1.508 (15)	C4F—H41F	0.9900
C31B—H31B	0.9900	C4F—H42F	0.9900
C31B—H32B	0.9900	S1F—C5F	1.799 (12)
C41B—S11B	1.799 (13)	C5F—H51F	0.9800
C41B—H41B	0.9900	C5F—H52F	0.9800
C41B—H42B	0.9900	C5F—H53F	0.9800
S11B—C5B	1.813 (16)	O1H—C1H	1.257 (11)
C22B—C32B	1.560 (16)	O2H—C1H	1.276 (11)
C22B—H22B	1.0000	N1H—C2H	1.488 (11)
C32B—C42B	1.508 (16)	N1H—H1H	0.9100
C32B—H33B	0.9900	N1H—H2H	0.9100
C32B—H34B	0.9900	N1H—H3H	0.9100
C42B—S12B	1.799 (13)	C1H—C2H	1.520 (13)
C42B—H43B	0.9900	C2H—C3H	1.530 (12)
C42B—H44B	0.9900	C2H—H21H	1.0000
S12B—C5B	1.75 (5)	C3H—C4H	1.520 (12)
C5B—H51B	0.9800	C3H—H31H	0.9900
C5B—H52B	0.9800	C3H—H32H	0.9900
C5B—H53B	0.9800	C4H—S1H	1.804 (9)
O1C—C1C	1.259 (11)	C4H—H41H	0.9900
O2C—C1C	1.253 (11)	C4H—H42H	0.9900
N1C—C21C	1.498 (11)	S1H—C5H	1.788 (12)
N1C—H1C	0.9100	C5H—H51H	0.9800
N1C—H2C	0.9100	C5H—H52H	0.9800
N1C—H3C	0.9100	C5H—H53H	0.9800
C1C—C21C	1.517 (14)
C21E—N1E—H1E	109.5	O1C—C1C—C21C	118.0 (8)
C21E—N1E—H2E	109.5	N1C—C21C—C1C	109.2 (7)
H1E—N1E—H2E	109.5	N1C—C21C—C31C	107.9 (8)
C21E—N1E—H3E	109.5	C1C—C21C—C31C	112.5 (9)
H1E—N1E—H3E	109.5	N1C—C21C—H21C	109.1
H2E—N1E—H3E	109.5	C1C—C21C—H21C	109.1
O1E—C1E—O2E	125.4 (9)	C31C—C21C—H21C	109.1
O1E—C1E—C22E	115 (3)	C41C—C31C—C21C	114.5 (10)
O2E—C1E—C22E	119 (3)	C41C—C31C—H31C	108.6
O1E—C1E—C21E	118.4 (18)	C21C—C31C—H31C	108.6
O2E—C1E—C21E	116.2 (17)	C41C—C31C—H32C	108.6
N1E—C21E—C31E	107 (3)	C21C—C31C—H32C	108.6
N1E—C21E—C1E	107.8 (19)	H31C—C31C—H32C	107.6
C31E—C21E—C1E	108.5 (18)	C31C—C41C—H41C	109.5
N1E—C21E—H21E	111.2	C31C—C41C—H42C	109.5
C31E—C21E—H21E	111.2	H41C—C41C—H42C	109.5
C1E—C21E—H21E	111.2	C31C—C41C—H43C	109.5
C41E—C31E—C21E	111.6 (19)	H41C—C41C—H43C	109.5
C41E—C31E—H31E	109.3	H42C—C41C—H43C	109.5
C21E—C31E—H31E	109.3	C42C—C32C—H33C	108.6
C41E—C31E—H32E	109.3	C42C—C32C—H34C	108.6
C21E—C31E—H32E	109.3	H33C—C32C—H34C	107.6
H31E—C31E—H32E	108.0	C32C—C42C—H44C	109.5
C31E—C41E—H41E	109.5	C32C—C42C—H45C	109.5
C31E—C41E—H42E	109.5	H44C—C42C—H45C	109.5
H41E—C41E—H42E	109.5	C32C—C42C—H46C	109.5
C31E—C41E—H43E	109.5	H44C—C42C—H46C	109.5
H41E—C41E—H43E	109.5	H45C—C42C—H46C	109.5
H42E—C41E—H43E	109.5	C2A—N1A—H1A	109.5
C1E—C22E—N1E	119 (4)	C2A—N1A—H2A	109.5
C1E—C22E—C32E	117 (3)	H1A—N1A—H2A	109.5
N1E—C22E—C32E	109 (4)	C2A—N1A—H3A	109.5
C1E—C22E—H22E	103.4	H1A—N1A—H3A	109.5
N1E—C22E—H22E	103.4	H2A—N1A—H3A	109.5
C32E—C22E—H22E	103.4	O1A—C1A—O2A	126.2 (9)
C42E—C32E—C22E	111.7 (19)	O1A—C1A—C2A	117.9 (8)
C42E—C32E—H33E	109.3	O2A—C1A—C2A	115.7 (8)
C22E—C32E—H33E	109.3	N1A—C2A—C3A	110.0 (7)
C42E—C32E—H34E	109.3	N1A—C2A—C1A	107.5 (7)
C22E—C32E—H34E	109.3	C3A—C2A—C1A	111.2 (8)
H33E—C32E—H34E	107.9	N1A—C2A—H21A	109.4
C32E—C42E—H44E	109.5	C3A—C2A—H21A	109.4
C32E—C42E—H45E	109.5	C1A—C2A—H21A	109.4
H44E—C42E—H45E	109.5	C4A—C3A—C2A	115.5 (9)
C32E—C42E—H46E	109.5	C4A—C3A—H31A	108.4
H44E—C42E—H46E	109.5	C2A—C3A—H31A	108.4
H45E—C42E—H46E	109.5	C4A—C3A—H32A	108.4
C21G—N1G—H1G	109.5	C2A—C3A—H32A	108.4
C21G—N1G—H2G	109.5	H31A—C3A—H32A	107.5
H1G—N1G—H2G	109.5	C3A—C4A—H41A	109.5
C21G—N1G—H3G	109.5	C3A—C4A—H42A	109.5
H1G—N1G—H3G	109.5	H41A—C4A—H42A	109.5
H2G—N1G—H3G	109.5	C3A—C4A—H43A	109.5
O1G—C1G—O2G	127.7 (9)	H41A—C4A—H43A	109.5
O1G—C1G—C21G	118.9 (12)	H42A—C4A—H43A	109.5
O2G—C1G—C21G	113.4 (12)	C2D—N1D—H1D	109.5
O1G—C1G—C22G	113 (2)	C2D—N1D—H2D	109.5
O2G—C1G—C22G	118.9 (19)	H1D—N1D—H2D	109.5
N1G—C21G—C31G	111.2 (16)	C2D—N1D—H3D	109.5
N1G—C21G—C1G	108.8 (15)	H1D—N1D—H3D	109.5
C31G—C21G—C1G	112.4 (13)	H2D—N1D—H3D	109.5
N1G—C21G—H21G	108.1	O2D—C1D—O1D	125.6 (9)
C31G—C21G—H21G	108.1	O2D—C1D—C2D	116.7 (8)
C1G—C21G—H21G	108.1	O1D—C1D—C2D	117.6 (8)
C21G—C31G—C41G	115.5 (13)	N1D—C2D—C1D	110.7 (8)
C21G—C31G—H31G	108.4	N1D—C2D—C3D	110.6 (7)
C41G—C31G—H31G	108.4	C1D—C2D—C3D	111.4 (7)
C21G—C31G—H32G	108.4	N1D—C2D—H21D	108.0
C41G—C31G—H32G	108.4	C1D—C2D—H21D	108.0
H31G—C31G—H32G	107.5	C3D—C2D—H21D	108.0
C31G—C41G—H41G	109.5	C4D—C3D—C2D	113.7 (8)
C31G—C41G—H42G	109.5	C4D—C3D—H3D1	108.8
H41G—C41G—H42G	109.5	C2D—C3D—H3D1	108.8
C31G—C41G—H43G	109.5	C4D—C3D—H3D2	108.8
H41G—C41G—H43G	109.5	C2D—C3D—H3D2	108.8
H42G—C41G—H43G	109.5	H3D1—C3D—H3D2	107.7
N1G—C22G—C32G	110 (3)	C3D—C4D—S1D	113.4 (7)
N1G—C22G—C1G	111 (3)	C3D—C4D—H41D	108.9
C32G—C22G—C1G	112 (3)	S1D—C4D—H41D	108.9
N1G—C22G—H22G	107.9	C3D—C4D—H42D	108.9
C32G—C22G—H22G	107.9	S1D—C4D—H42D	108.9
C1G—C22G—H22G	107.9	H41D—C4D—H42D	107.7
C22G—C32G—C42G	115.5 (13)	C5D—S1D—C4D	99.8 (5)
C22G—C32G—H33G	108.4	S1D—C5D—H51D	109.5
C42G—C32G—H33G	108.4	S1D—C5D—H52D	109.5
C22G—C32G—H34G	108.4	H51D—C5D—H52D	109.5
C42G—C32G—H34G	108.4	S1D—C5D—H53D	109.5
H33G—C32G—H34G	107.5	H51D—C5D—H53D	109.5
C32G—C42G—H44G	109.5	H52D—C5D—H53D	109.5
C32G—C42G—H45G	109.5	C2F—N1F—H1F	109.5
H44G—C42G—H45G	109.5	C2F—N1F—H2F	109.5
C32G—C42G—H46G	109.5	H1F—N1F—H2F	109.5
H44G—C42G—H46G	109.5	C2F—N1F—H3F	109.5
H45G—C42G—H46G	109.5	H1F—N1F—H3F	109.5
C21B—N1B—H1B	109.5	H2F—N1F—H3F	109.5
C21B—N1B—H2B	109.5	O1F—C1F—O2F	126.3 (9)
H1B—N1B—H2B	109.5	O1F—C1F—C2F	118.1 (8)
C21B—N1B—H3B	109.5	O2F—C1F—C2F	115.5 (8)
H1B—N1B—H3B	109.5	N1F—C2F—C3F	107.8 (8)
H2B—N1B—H3B	109.5	N1F—C2F—C1F	107.4 (7)
O1B—C1B—O2B	126.6 (8)	C3F—C2F—C1F	112.0 (8)
O1B—C1B—C21B	117.7 (10)	N1F—C2F—H21F	109.9
O2B—C1B—C21B	115.5 (10)	C3F—C2F—H21F	109.9
O1B—C1B—C22B	114 (3)	C1F—C2F—H21F	109.9
O2B—C1B—C22B	120 (3)	C2F—C3F—C4F	112.4 (8)
C1B—C21B—N1B	109.6 (10)	C2F—C3F—H31F	109.1
C1B—C21B—C31B	111.5 (9)	C4F—C3F—H31F	109.1
N1B—C21B—C31B	103.1 (12)	C2F—C3F—H32F	109.1
C1B—C21B—H21B	110.8	C4F—C3F—H32F	109.1
N1B—C21B—H21B	110.8	H31F—C3F—H32F	107.8
C31B—C21B—H21B	110.8	C3F—C4F—S1F	115.9 (7)
C41B—C31B—C21B	112.6 (11)	C3F—C4F—H41F	108.3
C41B—C31B—H31B	109.1	S1F—C4F—H41F	108.3
C21B—C31B—H31B	109.1	C3F—C4F—H42F	108.3
C41B—C31B—H32B	109.1	S1F—C4F—H42F	108.3
C21B—C31B—H32B	109.1	H41F—C4F—H42F	107.4
H31B—C31B—H32B	107.8	C4F—S1F—C5F	100.8 (5)
C31B—C41B—S11B	113.6 (9)	S1F—C5F—H51F	109.5
C31B—C41B—H41B	108.8	S1F—C5F—H52F	109.5
S11B—C41B—H41B	108.8	H51F—C5F—H52F	109.5
C31B—C41B—H42B	108.8	S1F—C5F—H53F	109.5
S11B—C41B—H42B	108.8	H51F—C5F—H53F	109.5
H41B—C41B—H42B	107.7	H52F—C5F—H53F	109.5
C41B—S11B—C5B	100.8 (7)	C2H—N1H—H1H	109.5
N1B—C22B—C32B	136 (7)	C2H—N1H—H2H	109.5
N1B—C22B—C1B	106 (4)	H1H—N1H—H2H	109.5
C32B—C22B—C1B	99 (4)	C2H—N1H—H3H	109.5
N1B—C22B—H22B	103.6	H1H—N1H—H3H	109.5
C32B—C22B—H22B	103.6	H2H—N1H—H3H	109.5
C1B—C22B—H22B	103.6	O1H—C1H—O2H	125.1 (9)
C42B—C32B—C22B	112.6 (12)	O1H—C1H—C2H	118.7 (8)
C42B—C32B—H33B	109.1	O2H—C1H—C2H	116.2 (8)
C22B—C32B—H33B	109.1	N1H—C2H—C1H	109.8 (7)
C42B—C32B—H34B	109.1	N1H—C2H—C3H	109.2 (7)
C22B—C32B—H34B	109.1	C1H—C2H—C3H	113.0 (7)
H33B—C32B—H34B	107.8	N1H—C2H—H21H	108.2
C32B—C42B—S12B	113.7 (9)	C1H—C2H—H21H	108.2
C32B—C42B—H43B	108.8	C3H—C2H—H21H	108.2
S12B—C42B—H43B	108.8	C4H—C3H—C2H	112.8 (7)
C32B—C42B—H44B	108.8	C4H—C3H—H31H	109.0
S12B—C42B—H44B	108.8	C2H—C3H—H31H	109.0
H43B—C42B—H44B	107.7	C4H—C3H—H32H	109.0
C5B—S12B—C42B	109 (2)	C2H—C3H—H32H	109.0
S11B—C5B—H51B	109.5	H31H—C3H—H32H	107.8
S11B—C5B—H52B	109.5	C3H—C4H—S1H	110.6 (7)
H51B—C5B—H52B	109.5	C3H—C4H—H41H	109.5
S11B—C5B—H53B	109.5	S1H—C4H—H41H	109.5
H51B—C5B—H53B	109.5	C3H—C4H—H42H	109.5
H52B—C5B—H53B	109.5	S1H—C4H—H42H	109.5
C21C—N1C—H1C	109.5	H41H—C4H—H42H	108.1
C21C—N1C—H2C	109.5	C5H—S1H—C4H	98.9 (5)
H1C—N1C—H2C	109.5	S1H—C5H—H51H	109.5
C21C—N1C—H3C	109.5	S1H—C5H—H52H	109.5
H1C—N1C—H3C	109.5	H51H—C5H—H52H	109.5
H2C—N1C—H3C	109.5	S1H—C5H—H53H	109.5
O2C—C1C—O1C	124.8 (9)	H51H—C5H—H53H	109.5
O2C—C1C—C21C	117.1 (8)	H52H—C5H—H53H	109.5
O1E—C1E—C21E—N1E	−21 (2)	C32B—C42B—S12B—C5B	−55 (5)
O2E—C1E—C21E—N1E	160.9 (13)	O2C—C1C—C21C—N1C	154.8 (8)
O1E—C1E—C21E—C31E	95 (2)	O1C—C1C—C21C—N1C	−28.7 (11)
O2E—C1E—C21E—C31E	−84 (3)	O2C—C1C—C21C—C31C	−85.4 (11)
N1E—C21E—C31E—C41E	178.9 (15)	O1C—C1C—C21C—C31C	91.1 (11)
C1E—C21E—C31E—C41E	63 (3)	N1C—C21C—C31C—C41C	−175.1 (10)
O1E—C1E—C22E—N1E	−15 (4)	C1C—C21C—C31C—C41C	64.4 (13)
O2E—C1E—C22E—N1E	163 (3)	N1C—C22C—C32C—C42C	98 (13)
O1E—C1E—C22E—C32E	118 (5)	O1A—C1A—C2A—N1A	−28.7 (11)
O2E—C1E—C22E—C32E	−64 (5)	O2A—C1A—C2A—N1A	156.5 (8)
C1E—C22E—C32E—C42E	−55 (7)	O1A—C1A—C2A—C3A	91.8 (10)
N1E—C22E—C32E—C42E	83 (4)	O2A—C1A—C2A—C3A	−83.0 (10)
O1G—C1G—C21G—N1G	−10.5 (14)	N1A—C2A—C3A—C4A	−61.1 (11)
O2G—C1G—C21G—N1G	167.4 (9)	C1A—C2A—C3A—C4A	179.9 (8)
O1G—C1G—C21G—C31G	113.2 (16)	O2D—C1D—C2D—N1D	−164.2 (8)
O2G—C1G—C21G—C31G	−69.0 (18)	O1D—C1D—C2D—N1D	18.1 (11)
N1G—C21G—C31G—C41G	74 (2)	O2D—C1D—C2D—C3D	72.3 (10)
C1G—C21G—C31G—C41G	−48 (2)	O1D—C1D—C2D—C3D	−105.4 (9)
O1G—C1G—C22G—N1G	−31 (3)	N1D—C2D—C3D—C4D	−76.5 (10)
O2G—C1G—C22G—N1G	156 (2)	C1D—C2D—C3D—C4D	47.0 (11)
O1G—C1G—C22G—C32G	92 (3)	C2D—C3D—C4D—S1D	−176.4 (6)
O2G—C1G—C22G—C32G	−81 (3)	C3D—C4D—S1D—C5D	70.4 (8)
N1G—C22G—C32G—C42G	−177 (3)	O1F—C1F—C2F—N1F	23.6 (11)
C1G—C22G—C32G—C42G	59 (4)	O2F—C1F—C2F—N1F	−160.1 (8)
O1B—C1B—C21B—N1B	25.7 (13)	O1F—C1F—C2F—C3F	−94.5 (10)
O2B—C1B—C21B—N1B	−157.9 (9)	O2F—C1F—C2F—C3F	81.8 (10)
O1B—C1B—C21B—C31B	−87.8 (13)	N1F—C2F—C3F—C4F	169.8 (8)
O2B—C1B—C21B—C31B	88.6 (14)	C1F—C2F—C3F—C4F	−72.3 (11)
C1B—C21B—C31B—C41B	−69.3 (15)	C2F—C3F—C4F—S1F	−69.1 (11)
N1B—C21B—C31B—C41B	173.2 (10)	C3F—C4F—S1F—C5F	−72.8 (9)
C21B—C31B—C41B—S11B	164.0 (10)	O1H—C1H—C2H—N1H	20.0 (12)
C31B—C41B—S11B—C5B	60.0 (11)	O2H—C1H—C2H—N1H	−160.8 (8)
O1B—C1B—C22B—N1B	24 (4)	O1H—C1H—C2H—C3H	−102.2 (10)
O2B—C1B—C22B—N1B	−158 (3)	O2H—C1H—C2H—C3H	77.0 (10)
O1B—C1B—C22B—C32B	−121 (3)	N1H—C2H—C3H—C4H	168.8 (8)
O2B—C1B—C22B—C32B	58 (4)	C1H—C2H—C3H—C4H	−68.7 (10)
N1B—C22B—C32B—C42B	−70 (10)	C2H—C3H—C4H—S1H	−168.5 (6)
C1B—C22B—C32B—C42B	56 (7)	C3H—C4H—S1H—C5H	−178.2 (8)
C22B—C32B—C42B—S12B	172 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O1G^i	0.91	1.89	2.800 (10)	174
N1A—H2A···O2D^ii	0.91	1.97	2.832 (10)	156
N1A—H3A···O2B^iii	0.91	1.96	2.852 (10)	166
C2A—H21A···O1C^i	1.00	2.39	3.231 (12)	142
N1B—H1B···O1H	0.91	1.88	2.774 (10)	168
N1B—H2B···O2A	0.91	1.93	2.840 (10)	175
N1B—H3B···O2C	0.91	1.90	2.793 (10)	168
C21B—H21B···O1D	1.00	2.43	3.242 (16)	138
N1C—H1C···O1E	0.91	1.85	2.746 (10)	167
N1C—H2C···O2B^iii	0.91	1.93	2.818 (10)	166
N1C—H3C···O2D^iii	0.91	1.92	2.818 (10)	171
C21C—H21C···O1A	1.00	2.35	3.235 (12)	147
N1D—H1D···O2C	0.91	1.95	2.834 (10)	163
N1D—H2D···O2A^iv	0.91	1.93	2.779 (10)	154
N1D—H3D···O1F^iv	0.91	1.89	2.769 (11)	162
C2D—H21D···O1B^iv	1.00	2.21	3.183 (12)	165
N1E—H1E···O2H	0.91	1.94	2.842 (10)	171
N1E—H2E···O1A	0.91	1.90	2.795 (10)	166
N1E—H3E···O2F	0.91	1.92	2.802 (10)	164
C21E—H21E···O1G^i	1.00	2.37	3.21 (3)	141
N1F—H1F···O2E^v	0.91	1.94	2.788 (10)	155
N1F—H2F···O1B	0.91	1.87	2.777 (10)	175
N1F—H3F···O2G^vi	0.91	1.95	2.833 (10)	163
C2F—H21F···O1H	1.00	2.36	3.160 (11)	136
N1G—H1G···O2F^iv	0.91	1.97	2.842 (10)	161
N1G—H2G···O1C	0.91	1.96	2.817 (10)	157
N1G—H3G···O2H	0.91	1.95	2.809 (10)	157
C21G—H21G···O1E	1.00	2.08	3.08 (2)	173
N1H—H1H···O2G^v	0.91	1.91	2.797 (10)	163
N1H—H2H···O1D	0.91	1.89	2.739 (10)	155
N1H—H3H···O2E^v	0.91	1.91	2.810 (10)	170
C2H—H21H···O1F^iv	1.00	2.20	3.181 (11)	168

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

(293) (S)-2-aminobutanoic acid–(R)-2-amino-4-(methylsulfanyl)butanoic acid (1/1)

Crystal data

C4H9NO2·C5H11NO2S	F(000) = 544
Mr = 252.33	Dx = 1.253 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 29.1721 (18) Å	Cell parameters from 3860 reflections
b = 4.7784 (3) Å	θ = 2.3–26.6°
c = 9.8551 (6) Å	µ = 0.24 mm^−1
β = 103.145 (2)°	T = 293 K
V = 1337.77 (14) Å^3	Plate, colorless
Z = 4	0.78 × 0.76 × 0.10 mm

Data collection

Bruker D8 Venture with Photon 100 CMOS detector diffractometer	2924 independent reflections
Radiation source: fine-focus sealed tube	1938 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 8.3 pixels mm^-1	θmax = 27.1°, θmin = 2.3°
Sets of exposures each taken over 0.5° ω rotation scans	h = −36→36
Absorption correction: multi-scan (TWINABS; Sheldrick, 2012)	k = −6→6
Tmin = 0.907, Tmax = 1.000	l = −12→11
9324 measured reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0605P)^2 + 0.2255P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.043	(Δ/σ)max < 0.001
wR(F^2) = 0.123	Δρmax = 0.14 e Å^−3
S = 1.04	Δρmin = −0.15 e Å^−3
2924 reflections	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
257 parameters	Extinction coefficient: 0.035 (5)
271 restraints	Absolute structure: Flack x determined using 724 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
Hydrogen site location: inferred from neighbouring sites	Absolute structure parameter: 0.02 (5)

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.

Refinement. The side chains of L-Abu and D-Met are disordered over three and four positions, repspectively. Restrainst were applied for molecular geometry with EADP constraints for thermal displacement parameters of equivalent atoms separated by < 1.2 angstrom.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	0.28775 (9)	0.5234 (9)	0.4654 (2)	0.0517 (9)
O2A	0.32151 (9)	0.7874 (9)	0.3310 (2)	0.0635 (11)
N1A	0.30377 (9)	0.8918 (9)	0.6726 (2)	0.0453 (11)
H1A	0.3129	1.0176	0.7399	0.068*
H2A	0.3058	0.7211	0.7097	0.068*
H3A	0.2741	0.9258	0.6285	0.068*
C1A	0.31155 (14)	0.7292 (11)	0.4435 (4)	0.0420 (13)
C21A	0.3354 (4)	0.910 (10)	0.570 (4)	0.0364 (16)	0.503 (11)
H21A	0.3379	1.1047	0.5407	0.044*	0.503 (11)
C31A	0.3836 (6)	0.798 (5)	0.639 (3)	0.063 (3)	0.503 (11)
H31A	0.3796	0.6085	0.6696	0.076*	0.503 (11)
H32A	0.4018	0.7851	0.5679	0.076*	0.503 (11)
C41A	0.4105 (4)	0.946 (3)	0.7521 (12)	0.131 (7)	0.503 (11)
H41A	0.4402	0.8538	0.7846	0.196*	0.503 (11)
H42A	0.3940	0.9525	0.8259	0.196*	0.503 (11)
H43A	0.4158	1.1331	0.7235	0.196*	0.503 (11)
C22A	0.3321 (6)	0.91 (2)	0.562 (8)	0.0364 (16)	0.253 (10)
H22A	0.3308	1.1045	0.5290	0.044*	0.253 (10)
C32A	0.3831 (10)	0.836 (13)	0.622 (5)	0.063 (3)	0.253 (10)
H33A	0.3927	0.9286	0.7121	0.076*	0.253 (10)
H34A	0.3847	0.6364	0.6398	0.076*	0.253 (10)
C42A	0.4163 (5)	0.902 (6)	0.544 (2)	0.104 (10)	0.253 (10)
H44A	0.4472	0.8501	0.5957	0.156*	0.253 (10)
H45A	0.4156	1.0997	0.5260	0.156*	0.253 (10)
H46A	0.4090	0.8019	0.4576	0.156*	0.253 (10)
C23A	0.3243 (7)	0.934 (9)	0.567 (4)	0.0364 (16)	0.244 (11)
H23A	0.3141	1.1191	0.5291	0.044*	0.244 (11)
C33A	0.3776 (8)	0.944 (6)	0.609 (3)	0.063 (3)	0.244 (11)
H35A	0.3889	1.0131	0.5298	0.076*	0.244 (11)
H36A	0.3863	1.0818	0.6827	0.076*	0.244 (11)
C43A	0.4018 (8)	0.696 (6)	0.655 (4)	0.125 (17)	0.244 (11)
H47A	0.4348	0.7352	0.6873	0.188*	0.244 (11)
H48A	0.3975	0.5649	0.5787	0.188*	0.244 (11)
H49A	0.3898	0.6164	0.7290	0.188*	0.244 (11)
O1B	0.28793 (9)	0.6506 (8)	−0.0356 (3)	0.0512 (9)
O2B	0.32233 (9)	0.3862 (9)	−0.1687 (2)	0.0607 (10)
N1B	0.30318 (9)	0.2820 (9)	0.1724 (2)	0.0434 (10)
H1B	0.3149	0.1525	0.2357	0.065*
H2B	0.2725	0.2518	0.1402	0.065*
H3B	0.3075	0.4508	0.2114	0.065*
C1B	0.31143 (13)	0.4472 (10)	−0.0566 (4)	0.0389 (11)
C21B	0.3277 (4)	0.267 (9)	0.055 (2)	0.0406 (18)	0.346 (10)
H21B	0.3185	0.0819	0.0144	0.049*	0.346 (10)
C31B	0.3815 (4)	0.232 (3)	0.1195 (19)	0.068 (5)	0.346 (10)
H31B	0.3861	0.1095	0.1997	0.082*	0.346 (10)
H32B	0.3967	0.1488	0.0515	0.082*	0.346 (10)
C41B	0.4034 (4)	0.518 (3)	0.1636 (18)	0.085 (6)	0.346 (10)
H41B	0.3879	0.6022	0.2309	0.103*	0.346 (10)
H42B	0.3989	0.6405	0.0831	0.103*	0.346 (10)
S11B	0.4656 (4)	0.483 (4)	0.2397 (18)	0.219 (10)	0.346 (10)
C51B	0.4837 (7)	0.428 (12)	0.083 (3)	0.350*	0.346 (10)
H51B	0.5174	0.4191	0.1022	0.525*	0.346 (10)
H52B	0.4728	0.5791	0.0201	0.525*	0.346 (10)
H53B	0.4707	0.2547	0.0417	0.525*	0.346 (10)
C22B	0.3345 (4)	0.261 (8)	0.074 (3)	0.0406 (18)	0.319 (7)
H22B	0.3369	0.0659	0.0452	0.049*	0.319 (7)
C32B	0.3845 (4)	0.392 (3)	0.1251 (15)	0.042 (5)	0.319 (7)
H33B	0.4015	0.3840	0.0512	0.050*	0.319 (7)
H34B	0.3817	0.5867	0.1497	0.050*	0.319 (7)
C42B	0.4116 (4)	0.230 (3)	0.2521 (11)	0.082 (6)	0.319 (7)
H43B	0.4143	0.0356	0.2271	0.098*	0.319 (7)
H44B	0.3945	0.2378	0.3256	0.098*	0.319 (7)
S12B	0.4696 (4)	0.376 (3)	0.3146 (15)	0.204 (6)	0.319 (7)
C52B	0.4883 (9)	0.142 (6)	0.454 (2)	0.350*	0.319 (7)
H54B	0.5193	0.1932	0.5050	0.525*	0.319 (7)
H55B	0.4890	−0.0446	0.4187	0.525*	0.319 (7)
H56B	0.4669	0.1498	0.5151	0.525*	0.319 (7)
C23B	0.3327 (5)	0.231 (6)	0.069 (5)	0.0406 (18)	0.263 (9)
H23B	0.3355	0.0358	0.0417	0.049*	0.263 (9)
C33B	0.3791 (5)	0.371 (3)	0.153 (2)	0.053 (8)	0.263 (9)
H35B	0.3732	0.5655	0.1704	0.063*	0.263 (9)
H36B	0.3895	0.2770	0.2418	0.063*	0.263 (9)
C43B	0.4174 (5)	0.350 (6)	0.0700 (15)	0.101 (8)	0.263 (9)
H45B	0.4070	0.4439	−0.0190	0.122*	0.263 (9)
H46B	0.4232	0.1554	0.0523	0.122*	0.263 (9)
S13B	0.4710 (5)	0.511 (5)	0.1665 (19)	0.171 (7)	0.263 (9)
C53B	0.4901 (10)	0.228 (9)	0.280 (4)	0.350*	0.263 (9)
H57B	0.5211	0.2657	0.3345	0.525*	0.263 (9)
H58B	0.4908	0.0607	0.2258	0.525*	0.263 (9)
H59B	0.4688	0.2021	0.3399	0.525*	0.263 (9)
C24B	0.3300 (7)	0.292 (12)	0.078 (4)	0.0406 (18)	0.070 (5)
H24B	0.3259	0.0991	0.0437	0.049*	0.070 (5)
C34B	0.3827 (8)	0.277 (5)	0.159 (4)	0.053 (8)	0.070 (5)
H37B	0.3897	0.4322	0.2242	0.063*	0.070 (5)
H38B	0.3882	0.1043	0.2122	0.063*	0.070 (5)
C44B	0.4147 (5)	0.290 (12)	0.057 (3)	0.101 (8)	0.070 (5)
H47B	0.4091	0.4626	0.0036	0.122*	0.070 (5)
H48B	0.4076	0.1348	−0.0084	0.122*	0.070 (5)
S14B	0.4758 (6)	0.273 (10)	0.148 (2)	0.171 (7)	0.070 (5)
C54B	0.5000	0.294 (18)	0.0000	0.19 (3)*	0.140 (10)
H60B	0.5337	0.3036	0.0289	0.282*	0.070 (5)
H61B	0.4883	0.4579	−0.0527	0.282*	0.070 (5)
H62B	0.4912	0.1305	−0.0568	0.282*	0.070 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0712 (17)	0.044 (3)	0.0406 (15)	−0.0119 (18)	0.0131 (13)	−0.0098 (15)
O2A	0.115 (2)	0.046 (3)	0.0353 (14)	0.000 (2)	0.0288 (14)	0.001 (2)
N1A	0.0648 (17)	0.040 (3)	0.0307 (15)	−0.001 (2)	0.0089 (15)	−0.0014 (18)
C1A	0.060 (2)	0.035 (4)	0.032 (2)	0.005 (2)	0.013 (2)	0.006 (2)
C21A	0.048 (4)	0.034 (3)	0.029 (3)	−0.002 (4)	0.013 (3)	−0.001 (3)
C31A	0.060 (4)	0.078 (12)	0.046 (7)	0.014 (6)	−0.001 (4)	0.016 (7)
C41A	0.084 (7)	0.130 (16)	0.145 (11)	0.027 (9)	−0.043 (7)	−0.068 (10)
C22A	0.048 (4)	0.034 (3)	0.029 (3)	−0.002 (4)	0.013 (3)	−0.001 (3)
C32A	0.060 (4)	0.078 (12)	0.046 (7)	0.014 (6)	−0.001 (4)	0.016 (7)
C42A	0.043 (8)	0.16 (2)	0.120 (16)	−0.014 (12)	0.036 (10)	0.005 (16)
C23A	0.048 (4)	0.034 (3)	0.029 (3)	−0.002 (4)	0.013 (3)	−0.001 (3)
C33A	0.060 (4)	0.078 (12)	0.046 (7)	0.014 (6)	−0.001 (4)	0.016 (7)
C43A	0.050 (15)	0.14 (3)	0.15 (3)	−0.025 (16)	−0.040 (16)	0.07 (2)
O1B	0.0721 (17)	0.036 (2)	0.0457 (16)	0.0035 (18)	0.0130 (14)	0.0007 (15)
O2B	0.109 (2)	0.043 (3)	0.0350 (14)	0.000 (2)	0.0287 (14)	−0.0014 (18)
N1B	0.0660 (17)	0.037 (3)	0.0296 (14)	−0.0062 (19)	0.0160 (14)	0.0052 (18)
C1B	0.060 (2)	0.027 (3)	0.029 (2)	−0.012 (2)	0.009 (2)	0.001 (2)
C21B	0.055 (3)	0.033 (4)	0.034 (3)	0.007 (3)	0.009 (2)	0.000 (3)
C31B	0.090 (11)	0.062 (9)	0.058 (9)	0.023 (8)	0.030 (8)	0.007 (8)
C41B	0.090 (12)	0.085 (12)	0.085 (11)	−0.021 (9)	0.025 (9)	−0.015 (9)
S11B	0.087 (6)	0.26 (2)	0.27 (2)	−0.046 (8)	−0.037 (10)	−0.051 (18)
C22B	0.055 (3)	0.033 (4)	0.034 (3)	0.007 (3)	0.009 (2)	0.000 (3)
C32B	0.044 (10)	0.044 (11)	0.044 (10)	0.004 (9)	0.023 (8)	0.003 (9)
C42B	0.066 (8)	0.105 (18)	0.066 (8)	0.003 (10)	−0.006 (7)	−0.001 (10)
S12B	0.119 (6)	0.263 (13)	0.187 (9)	−0.040 (7)	−0.057 (5)	0.059 (8)
C23B	0.055 (3)	0.033 (4)	0.034 (3)	0.007 (3)	0.009 (2)	0.000 (3)
C33B	0.045 (9)	0.057 (18)	0.058 (12)	0.010 (10)	0.016 (8)	0.014 (12)
C43B	0.077 (10)	0.136 (18)	0.086 (10)	−0.012 (12)	0.006 (8)	−0.004 (13)
S13B	0.085 (5)	0.203 (14)	0.210 (11)	−0.047 (7)	0.002 (6)	0.013 (11)
C24B	0.055 (3)	0.033 (4)	0.034 (3)	0.007 (3)	0.009 (2)	0.000 (3)
C34B	0.045 (9)	0.057 (18)	0.058 (12)	0.010 (10)	0.016 (8)	0.014 (12)
C44B	0.077 (10)	0.136 (18)	0.086 (10)	−0.012 (12)	0.006 (8)	−0.004 (13)
S14B	0.085 (5)	0.203 (14)	0.210 (11)	−0.047 (7)	0.002 (6)	0.013 (11)

Geometric parameters (Å, º)

O1A—C1A	1.251 (5)	C21B—C31B	1.563 (12)
O2A—C1A	1.240 (4)	C21B—H21B	0.9800
N1A—C23A	1.33 (4)	C31B—C41B	1.528 (13)
N1A—C22A	1.51 (6)	C31B—H31B	0.9700
N1A—C21A	1.52 (3)	C31B—H32B	0.9700
N1A—H1A	0.8900	C41B—S11B	1.805 (9)
N1A—H2A	0.8900	C41B—H41B	0.9700
N1A—H3A	0.8900	C41B—H42B	0.9700
C1A—C22A	1.47 (9)	S11B—C51B	1.761 (18)
C1A—C23A	1.54 (4)	C51B—H51B	0.9600
C1A—C21A	1.55 (4)	C51B—H52B	0.9600
C21A—C31A	1.513 (9)	C51B—H53B	0.9600
C21A—H21A	0.9800	C22B—C32B	1.564 (12)
C31A—C41A	1.40 (2)	C22B—H22B	0.9800
C31A—H31A	0.9700	C32B—C42B	1.529 (13)
C31A—H32A	0.9700	C32B—H33B	0.9700
C41A—H41A	0.9600	C32B—H34B	0.9700
C41A—H42A	0.9600	C42B—S12B	1.804 (9)
C41A—H43A	0.9600	C42B—H43B	0.9700
C22A—C32A	1.514 (9)	C42B—H44B	0.9700
C22A—H22A	0.9800	S12B—C52B	1.761 (18)
C32A—C42A	1.40 (2)	C52B—H54B	0.9600
C32A—H33A	0.9700	C52B—H55B	0.9600
C32A—H34A	0.9700	C52B—H56B	0.9600
C42A—H44A	0.9600	C23B—C33B	1.563 (12)
C42A—H45A	0.9600	C23B—H23B	0.9800
C42A—H46A	0.9600	C33B—C43B	1.529 (13)
C23A—C33A	1.514 (9)	C33B—H35B	0.9700
C23A—H23A	0.9800	C33B—H36B	0.9700
C33A—C43A	1.40 (2)	C43B—S13B	1.806 (9)
C33A—H35A	0.9700	C43B—H45B	0.9700
C33A—H36A	0.9700	C43B—H46B	0.9700
C43A—H47A	0.9600	S13B—C53B	1.761 (18)
C43A—H48A	0.9600	C53B—H57B	0.9600
C43A—H49A	0.9600	C53B—H58B	0.9600
O1B—C1B	1.233 (5)	C53B—H59B	0.9600
O2B—C1B	1.252 (4)	C24B—C34B	1.563 (12)
N1B—C24B	1.34 (3)	C24B—H24B	0.9800
N1B—C22B	1.48 (3)	C34B—C44B	1.528 (13)
N1B—C21B	1.50 (2)	C34B—H37B	0.9700
N1B—C23B	1.50 (5)	C34B—H38B	0.9700
N1B—H1B	0.8900	C44B—S14B	1.805 (9)
N1B—H2B	0.8900	C44B—H47B	0.9700
N1B—H3B	0.8900	C44B—H48B	0.9700
C1B—C21B	1.39 (3)	S14B—C54B	1.762 (18)
C1B—C24B	1.51 (3)	C54B—H60B	0.9600
C1B—C22B	1.58 (4)	C54B—H61B	0.9600
C1B—C23B	1.62 (3)	C54B—H62B	0.9600
C21A—N1A—H1A	109.5	C41B—C31B—H32B	109.7
C21A—N1A—H2A	109.5	C21B—C31B—H32B	109.7
H1A—N1A—H2A	109.5	H31B—C31B—H32B	108.2
C21A—N1A—H3A	109.5	C31B—C41B—S11B	110.5 (8)
H1A—N1A—H3A	109.5	C31B—C41B—H41B	109.6
H2A—N1A—H3A	109.5	S11B—C41B—H41B	109.6
O2A—C1A—O1A	125.7 (4)	C31B—C41B—H42B	109.6
O2A—C1A—C22A	116 (3)	S11B—C41B—H42B	109.6
O1A—C1A—C22A	118 (3)	H41B—C41B—H42B	108.1
O2A—C1A—C23A	119.9 (17)	C51B—S11B—C41B	97.1 (8)
O1A—C1A—C23A	114.1 (16)	S11B—C51B—H51B	109.5
O2A—C1A—C21A	116.1 (14)	S11B—C51B—H52B	109.5
O1A—C1A—C21A	117.8 (14)	H51B—C51B—H52B	109.5
C31A—C21A—N1A	109 (2)	S11B—C51B—H53B	109.5
C31A—C21A—C1A	111 (3)	H51B—C51B—H53B	109.5
N1A—C21A—C1A	105.9 (17)	H52B—C51B—H53B	109.5
C31A—C21A—H21A	110.2	N1B—C22B—C32B	115.4 (13)
N1A—C21A—H21A	110.2	N1B—C22B—C1B	106.5 (13)
C1A—C21A—H21A	110.2	C32B—C22B—C1B	103 (2)
C41A—C31A—C21A	118 (2)	N1B—C22B—H22B	110.4
C41A—C31A—H31A	107.8	C32B—C22B—H22B	110.4
C21A—C31A—H31A	107.8	C1B—C22B—H22B	110.4
C41A—C31A—H32A	107.8	C42B—C32B—C22B	109.5 (16)
C21A—C31A—H32A	107.8	C42B—C32B—H33B	109.8
H31A—C31A—H32A	107.1	C22B—C32B—H33B	109.8
C31A—C41A—H41A	109.5	C42B—C32B—H34B	109.8
C31A—C41A—H42A	109.5	C22B—C32B—H34B	109.8
H41A—C41A—H42A	109.5	H33B—C32B—H34B	108.2
C31A—C41A—H43A	109.5	C32B—C42B—S12B	110.8 (8)
H41A—C41A—H43A	109.5	C32B—C42B—H43B	109.5
H42A—C41A—H43A	109.5	S12B—C42B—H43B	109.5
C1A—C22A—N1A	110 (4)	C32B—C42B—H44B	109.5
C1A—C22A—C32A	111 (5)	S12B—C42B—H44B	109.5
N1A—C22A—C32A	111 (5)	H43B—C42B—H44B	108.1
C1A—C22A—H22A	108.2	C52B—S12B—C42B	97.0 (8)
N1A—C22A—H22A	108.2	S12B—C52B—H54B	109.5
C32A—C22A—H22A	108.2	S12B—C52B—H55B	109.5
C42A—C32A—C22A	118 (2)	H54B—C52B—H55B	109.5
C42A—C32A—H33A	107.8	S12B—C52B—H56B	109.5
C22A—C32A—H33A	107.8	H54B—C52B—H56B	109.5
C42A—C32A—H34A	107.8	H55B—C52B—H56B	109.5
C22A—C32A—H34A	107.8	N1B—C23B—C33B	98 (2)
H33A—C32A—H34A	107.1	N1B—C23B—C1B	103.6 (17)
C32A—C42A—H44A	109.5	C33B—C23B—C1B	105.5 (16)
C32A—C42A—H45A	109.5	N1B—C23B—H23B	115.9
H44A—C42A—H45A	109.5	C33B—C23B—H23B	115.9
C32A—C42A—H46A	109.5	C1B—C23B—H23B	115.9
H44A—C42A—H46A	109.5	C43B—C33B—C23B	109.9 (16)
H45A—C42A—H46A	109.5	C43B—C33B—H35B	109.7
N1A—C23A—C33A	114 (3)	C23B—C33B—H35B	109.7
N1A—C23A—C1A	117 (3)	C43B—C33B—H36B	109.7
C33A—C23A—C1A	107 (2)	C23B—C33B—H36B	109.7
N1A—C23A—H23A	106.2	H35B—C33B—H36B	108.2
C33A—C23A—H23A	106.2	C33B—C43B—S13B	110.1 (8)
C1A—C23A—H23A	106.2	C33B—C43B—H45B	109.6
C43A—C33A—C23A	118 (2)	S13B—C43B—H45B	109.6
C43A—C33A—H35A	107.8	C33B—C43B—H46B	109.6
C23A—C33A—H35A	107.8	S13B—C43B—H46B	109.6
C43A—C33A—H36A	107.8	H45B—C43B—H46B	108.2
C23A—C33A—H36A	107.8	C53B—S13B—C43B	96.8 (8)
H35A—C33A—H36A	107.1	S13B—C53B—H57B	109.5
C33A—C43A—H47A	109.5	S13B—C53B—H58B	109.5
C33A—C43A—H48A	109.5	H57B—C53B—H58B	109.5
H47A—C43A—H48A	109.5	S13B—C53B—H59B	109.5
C33A—C43A—H49A	109.5	H57B—C53B—H59B	109.5
H47A—C43A—H49A	109.5	H58B—C53B—H59B	109.5
H48A—C43A—H49A	109.5	N1B—C24B—C1B	118.4 (18)
C21B—N1B—H1B	109.5	N1B—C24B—C34B	108 (2)
C21B—N1B—H2B	109.5	C1B—C24B—C34B	126 (2)
H1B—N1B—H2B	109.5	N1B—C24B—H24B	99.4
C21B—N1B—H3B	109.5	C1B—C24B—H24B	99.4
H1B—N1B—H3B	109.5	C34B—C24B—H24B	99.4
H2B—N1B—H3B	109.5	C44B—C34B—C24B	109.8 (16)
O1B—C1B—O2B	126.4 (4)	C44B—C34B—H37B	109.7
O1B—C1B—C21B	117.3 (14)	C24B—C34B—H37B	109.7
O2B—C1B—C21B	116.3 (15)	C44B—C34B—H38B	109.7
O1B—C1B—C24B	110 (2)	C24B—C34B—H38B	109.7
O2B—C1B—C24B	123.4 (19)	H37B—C34B—H38B	108.2
O1B—C1B—C22B	117.2 (8)	C34B—C44B—S14B	110.5 (8)
O2B—C1B—C22B	116.0 (8)	C34B—C44B—H47B	109.5
O1B—C1B—C23B	120.3 (17)	S14B—C44B—H47B	109.5
O2B—C1B—C23B	113.3 (17)	C34B—C44B—H48B	109.5
C1B—C21B—N1B	116 (2)	S14B—C44B—H48B	109.5
C1B—C21B—C31B	121.1 (13)	H47B—C44B—H48B	108.1
N1B—C21B—C31B	107.6 (10)	C54B—S14B—C44B	96.9 (8)
C1B—C21B—H21B	103.1	S14B—C54B—H60B	109.5
N1B—C21B—H21B	103.1	S14B—C54B—H61B	109.5
C31B—C21B—H21B	103.1	H60B—C54B—H61B	109.5
C41B—C31B—C21B	109.9 (16)	S14B—C54B—H62B	109.5
C41B—C31B—H31B	109.7	H60B—C54B—H62B	109.5
C21B—C31B—H31B	109.7	H61B—C54B—H62B	109.5
C23A—N1A—C21A—C31A	175 (16)	O1B—C1B—C22B—N1B	29.4 (18)
C23A—N1A—C21A—C1A	−66 (13)	O2B—C1B—C22B—N1B	−156.4 (9)
O2A—C1A—C21A—C31A	−86 (2)	C21B—C1B—C22B—N1B	−62 (16)
O1A—C1A—C21A—C31A	87.8 (19)	C24B—C1B—C22B—N1B	23 (16)
C23A—C1A—C21A—C31A	163 (13)	C23B—C1B—C22B—N1B	−97 (22)
O2A—C1A—C21A—N1A	156.1 (15)	O1B—C1B—C22B—C32B	−92.5 (11)
O1A—C1A—C21A—N1A	−30 (3)	O2B—C1B—C22B—C32B	81.7 (12)
C23A—C1A—C21A—N1A	45 (10)	C21B—C1B—C22B—C32B	176 (17)
N1A—C21A—C31A—C41A	−66 (3)	C24B—C1B—C22B—C32B	−99 (16)
C1A—C21A—C31A—C41A	177.7 (19)	C23B—C1B—C22B—C32B	141 (22)
O2A—C1A—C22A—N1A	158 (3)	N1B—C22B—C32B—C42B	65 (3)
O1A—C1A—C22A—N1A	−25 (5)	C1B—C22B—C32B—C42B	−179.6 (7)
C23A—C1A—C22A—N1A	44 (21)	C22B—C32B—C42B—S12B	−179.9 (4)
O2A—C1A—C22A—C32A	−79 (5)	C32B—C42B—S12B—C52B	−180.0 (4)
O1A—C1A—C22A—C32A	98 (3)	C24B—N1B—C23B—C33B	63 (9)
C1A—C22A—C32A—C42A	71 (5)	C22B—N1B—C23B—C33B	40 (19)
N1A—C22A—C32A—C42A	−166 (6)	C21B—N1B—C23B—C33B	110 (11)
C21A—N1A—C23A—C33A	−26 (12)	C24B—N1B—C23B—C1B	−45 (9)
C21A—N1A—C23A—C1A	99 (15)	C22B—N1B—C23B—C1B	−68 (19)
O2A—C1A—C23A—N1A	165.3 (14)	C21B—N1B—C23B—C1B	2 (10)
O1A—C1A—C23A—N1A	−9 (2)	O1B—C1B—C23B—N1B	19.9 (15)
C21A—C1A—C23A—N1A	−119 (12)	O2B—C1B—C23B—N1B	−161.5 (10)
O2A—C1A—C23A—C33A	−66 (3)	C24B—C1B—C23B—N1B	40 (5)
O1A—C1A—C23A—C33A	120 (2)	C22B—C1B—C23B—N1B	76 (22)
C22A—C1A—C23A—C33A	5 (23)	O1B—C1B—C23B—C33B	−82 (2)
C21A—C1A—C23A—C33A	10 (10)	O2B—C1B—C23B—C33B	96 (2)
N1A—C23A—C33A—C43A	69 (5)	C24B—C1B—C23B—C33B	−62 (6)
C1A—C23A—C33A—C43A	−61 (5)	C22B—C1B—C23B—C33B	−26 (20)
O1B—C1B—C21B—N1B	19 (2)	N1B—C23B—C33B—C43B	180.0 (7)
O2B—C1B—C21B—N1B	−161.3 (13)	C1B—C23B—C33B—C43B	−73 (2)
C24B—C1B—C21B—N1B	55 (8)	C23B—C33B—C43B—S13B	−180.0 (4)
C22B—C1B—C21B—N1B	110 (18)	C33B—C43B—S13B—C53B	80 (2)
O1B—C1B—C21B—C31B	−115 (2)	C22B—N1B—C24B—C1B	144 (22)
O2B—C1B—C21B—C31B	65 (3)	C21B—N1B—C24B—C1B	68 (13)
C24B—C1B—C21B—C31B	−79 (5)	C23B—N1B—C24B—C1B	123 (12)
C22B—C1B—C21B—C31B	−24 (14)	C22B—N1B—C24B—C34B	−65 (16)
C24B—N1B—C21B—C1B	−99 (17)	C21B—N1B—C24B—C34B	−142 (18)
C22B—N1B—C21B—C1B	−141 (19)	C23B—N1B—C24B—C34B	−86 (8)
C23B—N1B—C21B—C1B	−178 (12)	O1B—C1B—C24B—N1B	34 (5)
C24B—N1B—C21B—C31B	40 (14)	O2B—C1B—C24B—N1B	−151 (3)
C22B—N1B—C21B—C31B	−2 (16)	C21B—C1B—C24B—N1B	−112 (8)
C23B—N1B—C21B—C31B	−38 (9)	C22B—C1B—C24B—N1B	−152 (20)
C1B—C21B—C31B—C41B	55 (3)	C23B—C1B—C24B—N1B	−127 (9)
N1B—C21B—C31B—C41B	−82 (2)	O1B—C1B—C24B—C34B	−111 (4)
C21B—C31B—C41B—S11B	179.6 (4)	O2B—C1B—C24B—C34B	64 (6)
C31B—C41B—S11B—C51B	75 (2)	C21B—C1B—C24B—C34B	103 (8)
C24B—N1B—C22B—C32B	83 (19)	C22B—C1B—C24B—C34B	63 (14)
C21B—N1B—C22B—C32B	145 (20)	C23B—C1B—C24B—C34B	88 (4)
C23B—N1B—C22B—C32B	−141 (22)	N1B—C24B—C34B—C44B	−179.5 (9)
C24B—N1B—C22B—C1B	−31 (18)	C1B—C24B—C34B—C44B	−32 (8)
C21B—N1B—C22B—C1B	31 (17)	C24B—C34B—C44B—S14B	−180.0 (4)
C23B—N1B—C22B—C1B	105 (19)	C34B—C44B—S14B—C54B	−179.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O2B^i	0.89	1.97	2.817 (5)	159
N1A—H2A···O2B^ii	0.89	1.99	2.862 (5)	165
N1A—H3A···O1A^iii	0.89	1.89	2.779 (4)	176
C21A—H21A···O1A^iv	0.98	2.49	3.31 (4)	141
N1B—H1B···O2A^v	0.89	1.97	2.817 (5)	158
N1B—H2B···O1B^vi	0.89	1.89	2.765 (4)	167
N1B—H3B···O2A	0.89	1.98	2.860 (5)	169
C21B—H21B···O1B^v	0.98	2.26	3.21 (4)	166

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