(4R,5S)-5-Benzyl-4-isopropyl-1,3,4-oxadiazinan-2-one.

The title compound, C(13)H(18)N(2)O(2), is an N(4)-isopropyl-l-phenyl-alanine-based oxadiazinanone. Although the two mol-ecules in the asymmetric unit are oriented appropriately for hydrogen bonding, the distance between the donor and acceptor atoms is large enough to support only weak, if any, hydrogen bonding. The absolute configuration is known based on the known starting compounds in the synthetic procedure.

Related literature

For related literature, see: Burgeson et al. (2004 ▶); Casper, Blackburn et al. (2002 ▶); Casper, Burgeson et al. (2002 ▶); Casper & Hitchcock (2003 ▶); Dore et al. (2006 ▶); Ferrence et al. (2003 ▶); Hitchcock et al. (2004 ▶); Hitchcock et al. (2001 ▶); Squire et al. (2005 ▶); Szczepura et al. (2004 ▶); Bruno et al. (2004 ▶).

Experimental

Crystal data

C13H18N2O2

M = 234.29

Orthorhombic,

a = 9.6423 (14) Å

b = 11.4974 (17) Å

c = 22.600 (3) Å

V = 2505.5 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 (2) K

0.43 × 0.23 × 0.23 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan SADABS in SAINT-Plus (Bruker, 2003 ▶) T min = 0.965, T max = 0.981

25602 measured reflections

3499 independent reflections

3403 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.133

S = 1.32

3499 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAIn class="Chemical">NT-Plus; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013056/sg2243sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013056/sg2243Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Enhanced figure: interactive version of Fig. 5

C13H18N2O2	F000 = 1008
Mr = 234.29	Dx = 1.242 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8817 reflections
a = 9.6423 (14) Å	θ = 2.3–30.5º
b = 11.4974 (17) Å	µ = 0.09 mm−1
c = 22.600 (3) Å	T = 100 (2) K
V = 2505.5 (6) Å3	Block, colourless
Z = 8	0.43 × 0.23 × 0.23 mm

Bruker SMART APEX CCD diffractometer	3403 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.041
Monochromator: graphite	θmax = 28.3º
ω scans	θmin = 1.8º
Absorption correction: multi-scanSADABS in SAINT-Plus (Bruker, 2003)	h = −12→12
Tmin = 0.965, Tmax = 0.981	k = −15→15
25602 measured reflections	l = −29→30
3499 independent reflections

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0413P)2 + 1.6549P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.060	(Δ/σ)max < 0.001
wR(F2) = 0.133	Δρmax = 0.37 e Å−3
S = 1.32	Δρmin = −0.25 e Å−3
3499 reflections	Extinction correction: none
307 parameters

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.

	x	y	z	Uiso*/Ueq
O1A	0.5275 (2)	0.74524 (18)	0.71574 (9)	0.0200 (4)
C2A	0.5986 (3)	0.7897 (3)	0.76134 (13)	0.0176 (6)
O17A	0.6692 (2)	0.87684 (18)	0.75304 (9)	0.0213 (4)
N3A	0.5897 (2)	0.7389 (2)	0.81457 (10)	0.0170 (5)
H3A	0.6512	0.7603	0.8412	0.02*
N4A	0.4904 (2)	0.6534 (2)	0.83257 (10)	0.0154 (5)
C5A	0.3806 (3)	0.6483 (2)	0.78779 (12)	0.0165 (5)
H5A	0.3265	0.5752	0.7943	0.02*
C6A	0.4435 (3)	0.6429 (3)	0.72638 (13)	0.0191 (6)
H6A1	0.5015	0.5723	0.7227	0.023*
H6A2	0.3687	0.6385	0.6964	0.023*
C7A	0.2806 (3)	0.7517 (3)	0.79456 (13)	0.0206 (6)
H7A1	0.3317	0.8247	0.7865	0.025*
H7A2	0.2059	0.7447	0.7647	0.025*
C8A	0.2163 (3)	0.7588 (3)	0.85530 (13)	0.0189 (6)
C9A	0.0827 (3)	0.7173 (3)	0.86541 (14)	0.0232 (6)
H9A	0.031	0.686	0.8333	0.028*
C10A	0.0233 (3)	0.7206 (3)	0.92131 (15)	0.0263 (7)
H10A	−0.0681	0.6921	0.9273	0.032*
C11A	0.0976 (3)	0.7656 (3)	0.96826 (14)	0.0251 (7)
H11A	0.0584	0.7669	1.0068	0.03*
C12A	0.2293 (3)	0.8086 (3)	0.95870 (15)	0.0281 (7)
H12A	0.2802	0.8407	0.9908	0.034*
C13A	0.2878 (3)	0.8053 (3)	0.90287 (15)	0.0249 (7)
H13A	0.3786	0.8354	0.8971	0.03*
C14A	0.5541 (3)	0.5392 (2)	0.84671 (13)	0.0180 (6)
H14A	0.5723	0.4953	0.8093	0.022*
C15A	0.6894 (3)	0.5566 (3)	0.88013 (14)	0.0250 (7)
H15A	0.7547	0.5999	0.8552	0.037*
H15B	0.7291	0.4808	0.8902	0.037*
H15C	0.6714	0.6006	0.9165	0.037*
C16A	0.4514 (4)	0.4714 (3)	0.88512 (15)	0.0285 (7)
H16A	0.3644	0.4606	0.8633	0.043*
H16B	0.4331	0.5149	0.9216	0.043*
H16C	0.4908	0.3952	0.895	0.043*
O1B	0.8672 (2)	0.98233 (18)	0.94720 (9)	0.0218 (5)
C2B	0.7980 (3)	0.9425 (2)	0.89999 (13)	0.0175 (5)
O17B	0.7047 (2)	0.87193 (19)	0.90751 (9)	0.0221 (5)
N3B	0.8282 (3)	0.9856 (2)	0.84613 (11)	0.0187 (5)
H3B	0.7824	0.955	0.8163	0.022*
N4B	0.9257 (3)	1.0754 (2)	0.83144 (11)	0.0177 (5)
C5B	0.9584 (3)	1.1386 (2)	0.88641 (13)	0.0188 (6)
H5B	1.0451	1.1841	0.8792	0.023*
C6B	0.9879 (3)	1.0537 (2)	0.93632 (14)	0.0200 (6)
H6B1	1.0676	1.0036	0.9256	0.024*
H6B2	1.0123	1.0971	0.9727	0.024*
C7B	0.8430 (3)	1.2258 (3)	0.90152 (14)	0.0216 (6)
H7B1	0.8272	1.2779	0.8673	0.026*
H7B2	0.7558	1.1832	0.9094	0.026*
C8B	0.8812 (3)	1.2979 (2)	0.95530 (14)	0.0205 (6)
C9B	0.9766 (4)	1.3882 (3)	0.95059 (15)	0.0261 (7)
H9B	1.0129	1.4084	0.9129	0.031*
C10B	1.0197 (4)	1.4496 (3)	1.00054 (16)	0.0291 (7)
H10B	1.0845	1.5114	0.9968	0.035*
C11B	0.9680 (4)	1.4202 (3)	1.05520 (17)	0.0325 (8)
H11B	0.9978	1.4613	1.0894	0.039*
C12B	0.8727 (4)	1.3309 (3)	1.06053 (16)	0.0341 (8)
H12B	0.8368	1.3108	1.0983	0.041*
C13B	0.8296 (4)	1.2707 (3)	1.01068 (15)	0.0286 (7)
H13B	0.7636	1.2099	1.0146	0.034*
C14B	1.0493 (3)	1.0225 (3)	0.80199 (13)	0.0207 (6)
H14B	1.0973	0.9692	0.8303	0.025*
C15B	1.0028 (4)	0.9540 (3)	0.74778 (15)	0.0255 (6)
H15D	0.9394	0.8919	0.76	0.038*
H15E	1.084	0.9198	0.7283	0.038*
H15F	0.9553	1.0062	0.7201	0.038*
C16B	1.1483 (4)	1.1180 (3)	0.78295 (15)	0.0320 (8)
H16D	1.1788	1.1619	0.8178	0.048*
H16E	1.101	1.1705	0.7554	0.048*
H16F	1.229	1.0833	0.7634	0.048*

	U11	U22	U33	U12	U13	U23
O1A	0.0219 (10)	0.0205 (10)	0.0176 (9)	−0.0022 (9)	−0.0014 (8)	0.0017 (8)
C2A	0.0151 (12)	0.0162 (13)	0.0215 (14)	0.0042 (11)	−0.0003 (11)	−0.0015 (11)
O17A	0.0237 (10)	0.0186 (10)	0.0217 (10)	−0.0034 (9)	−0.0026 (9)	0.0017 (9)
N3A	0.0147 (11)	0.0186 (11)	0.0178 (11)	−0.0011 (10)	−0.0048 (9)	−0.0007 (9)
N4A	0.0146 (11)	0.0122 (10)	0.0193 (11)	0.0005 (9)	−0.0011 (9)	0.0018 (9)
C5A	0.0141 (12)	0.0171 (12)	0.0182 (13)	−0.0037 (11)	−0.0020 (10)	0.0000 (11)
C6A	0.0199 (14)	0.0189 (13)	0.0185 (14)	−0.0034 (12)	−0.0037 (11)	−0.0001 (11)
C7A	0.0178 (13)	0.0234 (15)	0.0207 (14)	0.0031 (12)	−0.0033 (11)	0.0025 (12)
C8A	0.0175 (13)	0.0149 (13)	0.0243 (14)	0.0059 (11)	−0.0035 (11)	0.0008 (11)
C9A	0.0196 (14)	0.0234 (14)	0.0267 (15)	−0.0036 (13)	−0.0054 (12)	−0.0021 (13)
C10A	0.0217 (15)	0.0255 (15)	0.0317 (16)	−0.0036 (13)	0.0020 (13)	0.0049 (13)
C11A	0.0286 (16)	0.0246 (15)	0.0221 (14)	0.0080 (14)	0.0000 (13)	0.0029 (12)
C12A	0.0248 (15)	0.0331 (18)	0.0265 (16)	0.0082 (14)	−0.0089 (13)	−0.0110 (14)
C13A	0.0147 (13)	0.0271 (16)	0.0329 (17)	0.0028 (12)	−0.0013 (12)	−0.0063 (13)
C14A	0.0232 (14)	0.0139 (12)	0.0169 (13)	0.0039 (11)	−0.0021 (11)	0.0013 (10)
C15A	0.0276 (16)	0.0234 (15)	0.0239 (15)	0.0076 (13)	−0.0055 (13)	0.0013 (12)
C16A	0.0364 (18)	0.0229 (15)	0.0262 (15)	−0.0040 (14)	−0.0032 (14)	0.0086 (13)
O1B	0.0249 (11)	0.0187 (10)	0.0218 (10)	−0.0014 (9)	−0.0009 (9)	0.0005 (9)
C2B	0.0183 (13)	0.0134 (12)	0.0207 (13)	0.0045 (11)	0.0003 (11)	−0.0028 (11)
O17B	0.0254 (11)	0.0210 (10)	0.0197 (10)	−0.0059 (9)	0.0037 (9)	−0.0019 (8)
N3B	0.0194 (12)	0.0183 (12)	0.0185 (11)	−0.0044 (10)	−0.0018 (10)	0.0001 (9)
N4B	0.0174 (11)	0.0136 (10)	0.0222 (12)	−0.0026 (9)	−0.0005 (9)	0.0021 (9)
C5B	0.0183 (13)	0.0146 (12)	0.0233 (14)	−0.0044 (11)	−0.0033 (11)	0.0017 (11)
C6B	0.0190 (13)	0.0160 (12)	0.0249 (15)	0.0004 (11)	−0.0045 (12)	0.0010 (11)
C7B	0.0202 (13)	0.0159 (13)	0.0286 (15)	0.0020 (11)	−0.0040 (12)	−0.0003 (12)
C8B	0.0190 (13)	0.0141 (13)	0.0284 (15)	0.0063 (11)	−0.0065 (12)	−0.0013 (11)
C9B	0.0283 (16)	0.0179 (14)	0.0319 (17)	0.0011 (13)	−0.0076 (14)	0.0023 (13)
C10B	0.0257 (16)	0.0160 (14)	0.046 (2)	0.0012 (13)	−0.0127 (15)	−0.0024 (14)
C11B	0.0362 (19)	0.0232 (15)	0.0382 (19)	0.0108 (15)	−0.0117 (16)	−0.0114 (14)
C12B	0.0343 (18)	0.0376 (19)	0.0305 (17)	0.0087 (16)	0.0041 (15)	−0.0045 (15)
C13B	0.0257 (15)	0.0237 (17)	0.0365 (18)	0.0026 (14)	0.0035 (14)	−0.0045 (14)
C14B	0.0161 (13)	0.0246 (14)	0.0215 (14)	0.0050 (12)	0.0007 (11)	0.0062 (12)
C15B	0.0250 (14)	0.0223 (14)	0.0291 (15)	−0.0023 (13)	0.0086 (12)	−0.0022 (13)
C16B	0.0276 (16)	0.045 (2)	0.0236 (16)	−0.0147 (16)	0.0054 (13)	−0.0039 (15)

O1A—C2A	1.339 (3)	O1B—C2B	1.339 (3)
O1A—C6A	1.449 (3)	O1B—C6B	1.444 (4)
C2A—O17A	1.226 (4)	C2B—O17B	1.223 (4)
C2A—N3A	1.340 (4)	C2B—N3B	1.346 (4)
N3A—N4A	1.431 (3)	N3B—N4B	1.435 (3)
N3A—H3A	0.88	N3B—H3B	0.88
N4A—C5A	1.466 (3)	N4B—C5B	1.474 (4)
N4A—C14A	1.484 (3)	N4B—C14B	1.494 (4)
C5A—C6A	1.516 (4)	C5B—C6B	1.519 (4)
C5A—C7A	1.538 (4)	C5B—C7B	1.536 (4)
C5A—H5A	1	C5B—H5B	1
C6A—H6A1	0.99	C6B—H6B1	0.99
C6A—H6A2	0.99	C6B—H6B2	0.99
C7A—C8A	1.508 (4)	C7B—C8B	1.517 (4)
C7A—H7A1	0.99	C7B—H7B1	0.99
C7A—H7A2	0.99	C7B—H7B2	0.99
C8A—C13A	1.385 (4)	C8B—C13B	1.383 (5)
C8A—C9A	1.393 (4)	C8B—C9B	1.391 (4)
C9A—C10A	1.388 (4)	C9B—C10B	1.394 (5)
C9A—H9A	0.95	C9B—H9B	0.95
C10A—C11A	1.381 (5)	C10B—C11B	1.374 (5)
C10A—H10A	0.95	C10B—H10B	0.95
C11A—C12A	1.380 (5)	C11B—C12B	1.383 (5)
C11A—H11A	0.95	C11B—H11B	0.95
C12A—C13A	1.383 (5)	C12B—C13B	1.386 (5)
C12A—H12A	0.95	C12B—H12B	0.95
C13A—H13A	0.95	C13B—H13B	0.95
C14A—C15A	1.521 (4)	C14B—C16B	1.517 (4)
C14A—C16A	1.530 (4)	C14B—C15B	1.524 (5)
C14A—H14A	1	C14B—H14B	1
C15A—H15A	0.98	C15B—H15D	0.98
C15A—H15B	0.98	C15B—H15E	0.98
C15A—H15C	0.98	C15B—H15F	0.98
C16A—H16A	0.98	C16B—H16D	0.98
C16A—H16B	0.98	C16B—H16E	0.98
C16A—H16C	0.98	C16B—H16F	0.98
C2A—O1A—C6A	117.9 (2)	C2B—O1B—C6B	117.4 (2)
O17A—C2A—O1A	118.6 (3)	O17B—C2B—O1B	118.9 (3)
O17A—C2A—N3A	121.9 (3)	O17B—C2B—N3B	121.9 (3)
O1A—C2A—N3A	119.5 (3)	O1B—C2B—N3B	119.1 (3)
C2A—N3A—N4A	126.7 (2)	C2B—N3B—N4B	128.0 (2)
C2A—N3A—H3A	116.7	C2B—N3B—H3B	116
N4A—N3A—H3A	116.7	N4B—N3B—H3B	116
N3A—N4A—C5A	108.3 (2)	N3B—N4B—C5B	107.4 (2)
N3A—N4A—C14A	113.1 (2)	N3B—N4B—C14B	109.5 (2)
C5A—N4A—C14A	114.3 (2)	C5B—N4B—C14B	114.0 (2)
N4A—C5A—C6A	110.2 (2)	N4B—C5B—C6B	110.4 (2)
N4A—C5A—C7A	110.7 (2)	N4B—C5B—C7B	110.8 (2)
C6A—C5A—C7A	111.9 (2)	C6B—C5B—C7B	113.0 (3)
N4A—C5A—H5A	108	N4B—C5B—H5B	107.5
C6A—C5A—H5A	108	C6B—C5B—H5B	107.5
C7A—C5A—H5A	108	C7B—C5B—H5B	107.5
O1A—C6A—C5A	110.1 (2)	O1B—C6B—C5B	109.9 (2)
O1A—C6A—H6A1	109.6	O1B—C6B—H6B1	109.7
C5A—C6A—H6A1	109.6	C5B—C6B—H6B1	109.7
O1A—C6A—H6A2	109.6	O1B—C6B—H6B2	109.7
C5A—C6A—H6A2	109.6	C5B—C6B—H6B2	109.7
H6A1—C6A—H6A2	108.2	H6B1—C6B—H6B2	108.2
C8A—C7A—C5A	112.9 (2)	C8B—C7B—C5B	111.1 (2)
C8A—C7A—H7A1	109	C8B—C7B—H7B1	109.4
C5A—C7A—H7A1	109	C5B—C7B—H7B1	109.4
C8A—C7A—H7A2	109	C8B—C7B—H7B2	109.4
C5A—C7A—H7A2	109	C5B—C7B—H7B2	109.4
H7A1—C7A—H7A2	107.8	H7B1—C7B—H7B2	108
C13A—C8A—C9A	117.8 (3)	C13B—C8B—C9B	118.4 (3)
C13A—C8A—C7A	121.5 (3)	C13B—C8B—C7B	120.9 (3)
C9A—C8A—C7A	120.7 (3)	C9B—C8B—C7B	120.5 (3)
C10A—C9A—C8A	121.4 (3)	C8B—C9B—C10B	120.8 (3)
C10A—C9A—H9A	119.3	C8B—C9B—H9B	119.6
C8A—C9A—H9A	119.3	C10B—C9B—H9B	119.6
C11A—C10A—C9A	119.7 (3)	C11B—C10B—C9B	119.7 (3)
C11A—C10A—H10A	120.1	C11B—C10B—H10B	120.2
C9A—C10A—H10A	120.1	C9B—C10B—H10B	120.2
C12A—C11A—C10A	119.4 (3)	C10B—C11B—C12B	120.1 (3)
C12A—C11A—H11A	120.3	C10B—C11B—H11B	119.9
C10A—C11A—H11A	120.3	C12B—C11B—H11B	119.9
C11A—C12A—C13A	120.6 (3)	C11B—C12B—C13B	119.9 (3)
C11A—C12A—H12A	119.7	C11B—C12B—H12B	120
C13A—C12A—H12A	119.7	C13B—C12B—H12B	120
C12A—C13A—C8A	121.0 (3)	C8B—C13B—C12B	121.0 (3)
C12A—C13A—H13A	119.5	C8B—C13B—H13B	119.5
C8A—C13A—H13A	119.5	C12B—C13B—H13B	119.5
N4A—C14A—C15A	110.2 (2)	N4B—C14B—C16B	109.5 (3)
N4A—C14A—C16A	107.8 (2)	N4B—C14B—C15B	109.5 (2)
C15A—C14A—C16A	109.9 (2)	C16B—C14B—C15B	109.3 (3)
N4A—C14A—H14A	109.7	N4B—C14B—H14B	109.5
C15A—C14A—H14A	109.7	C16B—C14B—H14B	109.5
C16A—C14A—H14A	109.7	C15B—C14B—H14B	109.5
C14A—C15A—H15A	109.5	C14B—C15B—H15D	109.5
C14A—C15A—H15B	109.5	C14B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
C14A—C15A—H15C	109.5	C14B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C14A—C16A—H16A	109.5	C14B—C16B—H16D	109.5
C14A—C16A—H16B	109.5	C14B—C16B—H16E	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16E	109.5
C14A—C16A—H16C	109.5	C14B—C16B—H16F	109.5
H16A—C16A—H16C	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16C	109.5	H16E—C16B—H16F	109.5
C6A—O1A—C2A—O17A	−179.4 (2)	C6B—O1B—C2B—O17B	172.3 (2)
C6A—O1A—C2A—N3A	−0.1 (4)	C6B—O1B—C2B—N3B	−11.2 (4)
O17A—C2A—N3A—N4A	166.0 (3)	O17B—C2B—N3B—N4B	174.2 (3)
O1A—C2A—N3A—N4A	−13.3 (4)	O1B—C2B—N3B—N4B	−2.2 (4)
C2A—N3A—N4A—C5A	−12.3 (4)	C2B—N3B—N4B—C5B	−17.0 (4)
C2A—N3A—N4A—C14A	115.5 (3)	C2B—N3B—N4B—C14B	107.2 (3)
N3A—N4A—C5A—C6A	47.0 (3)	N3B—N4B—C5B—C6B	46.5 (3)
C14A—N4A—C5A—C6A	−80.2 (3)	C14B—N4B—C5B—C6B	−75.0 (3)
N3A—N4A—C5A—C7A	−77.3 (3)	N3B—N4B—C5B—C7B	−79.5 (3)
C14A—N4A—C5A—C7A	155.5 (2)	C14B—N4B—C5B—C7B	159.1 (2)
C2A—O1A—C6A—C5A	35.5 (3)	C2B—O1B—C6B—C5B	41.9 (3)
N4A—C5A—C6A—O1A	−60.1 (3)	N4B—C5B—C6B—O1B	−61.0 (3)
C7A—C5A—C6A—O1A	63.5 (3)	C7B—C5B—C6B—O1B	63.7 (3)
N4A—C5A—C7A—C8A	−56.9 (3)	N4B—C5B—C7B—C8B	−175.5 (2)
C6A—C5A—C7A—C8A	179.9 (2)	C6B—C5B—C7B—C8B	60.0 (3)
C5A—C7A—C8A—C13A	79.7 (4)	C5B—C7B—C8B—C13B	−99.3 (3)
C5A—C7A—C8A—C9A	−99.6 (3)	C5B—C7B—C8B—C9B	76.3 (3)
C13A—C8A—C9A—C10A	−0.9 (5)	C13B—C8B—C9B—C10B	0.3 (5)
C7A—C8A—C9A—C10A	178.4 (3)	C7B—C8B—C9B—C10B	−175.4 (3)
C8A—C9A—C10A—C11A	−0.2 (5)	C8B—C9B—C10B—C11B	0.4 (5)
C9A—C10A—C11A—C12A	1.1 (5)	C9B—C10B—C11B—C12B	−0.6 (5)
C10A—C11A—C12A—C13A	−1.0 (5)	C10B—C11B—C12B—C13B	0.2 (5)
C11A—C12A—C13A—C8A	−0.2 (5)	C9B—C8B—C13B—C12B	−0.7 (5)
C9A—C8A—C13A—C12A	1.1 (5)	C7B—C8B—C13B—C12B	175.0 (3)
C7A—C8A—C13A—C12A	−178.3 (3)	C11B—C12B—C13B—C8B	0.5 (5)
N3A—N4A—C14A—C15A	40.3 (3)	N3B—N4B—C14B—C16B	176.4 (2)
C5A—N4A—C14A—C15A	164.9 (2)	C5B—N4B—C14B—C16B	−63.2 (3)
N3A—N4A—C14A—C16A	160.2 (2)	N3B—N4B—C14B—C15B	56.5 (3)
C5A—N4A—C14A—C16A	−75.2 (3)	C5B—N4B—C14B—C15B	176.9 (2)