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

The title compound, C₁₃H₁₈N₂O₂, is an N₄-isopropyl-L-phenyl­alanine-based oxadiazinanone. Although the two mol­ecules 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.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.060
• wR factor = 0.134
• Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

Author Response: The few low precision bonds above the test threshold are only barely so. The refinement seems to be the best possible for the dataset. Having two independent molecules in the unit cell provides access to better average bond precision for those in question.

PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Author Response: SADABS calculated a "Ratio of minimum to maximum apparent transmission: 0.859376". This seems anomalously low for a C,H,N,O structure, but commonly occurs when using SADABS. The values calculated by SHELXL seem to be equally meaningful, so they were reported unchanged.

PLAT720_ALERT_4_C Number of Unusual/Non-Standard Labels ..........          8

Author Response: Our labeling scheme was analogous to past related structures.

PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C13 H18 N2 O2

Author Response: Choice of residue location is better for H-bond viewing when looking at asymmetric unit alone.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.28
           From the CIF: _reflns_number_total               3499
           Count of symmetry unique reflns         3498
           Completeness (_total/calc)            100.03%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         1
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

Author Response: MERG 4 gives 3499 unique reflections; MERG 2 gives 6209 unique reflections, so there are 2710 Friedel pairs that were measured; however, final refinement was carried out using MERG 4.

PLAT791_ALERT_4_G Confirm the Absolute Configuration of C5A    ...          S

Author Response: We have checked them carefully and they are correctly assigned.

PLAT791_ALERT_4_G Confirm the Absolute Configuration of C5B    ...          S

Author Response: We have checked them carefully and they are correctly assigned.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

The synthesis (Hitchcock et al., 2001), conformational analysis (Casper, Blackburn et al., 2002; Burgeson et al. 2004), and asymmetric applications (Casper & Hitchcock, 2003; Casper, Burgeson et al., 2002; Ferrence et al. 2003; Hitchcock et al. 2004; Hitchcock et al. 2001; Squire et al. 2005; Szczepura et al. 2004) of 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazinan-2-ones have only thoroughly been studied in the last ten years. We have been interested in synthesizing new oxadiazinanones for use as chiral auxillaries in aldol addition reactions. We synthesized the title compound in order to study the conformation that the heterocycle adopts. Herein we report the single-crystal X-ray structure analysis of the N₄-isopropyl-L-phenylalanine based oxiadiazinanone.

Other oxadiazinanones have been reported and studied, but the title compound is one of few studied that is not substituted at the N3 position. Other oxadiazinanone structures (Burgeson et al., 2004; Casper, Blackburn et al., 2002; Casper, Burgeson et al., 2002; Ferrence et al., 2003; Hitchcock et al., 2001, 2004) are substituted with a carbonyl at the N3 position. These N3 substituted oxadiazinanones adopt a twist-boat conformation, as does the title compound. This is also consistent with related oxadiazinanones not substituted at the N3 position (Szczepura et al., 2004). The C7B—C5B—N4B—C14B torsion angle is 159.1 (2)°, and the C7A—C5A—N4A—C14A torsion angle is 155.5 (2)°. Previously reported oxadiazinanones with no substitution at the N3 position have torsion angles between 161.79–163.16°. A Mogul (Bruno et al. 2004) geometry check showed all non-H bond angles and distances to be normal. The molecular structure (Fig. 1.) of I includes two independent molecules in the asymmetric unit. The oxadiazinanone moieties are essentially isostructural. The primary difference between the two molecules is the orientation of the benzyl group attached to C5A/B (Figs. 2. and 3.). The respective -56.9 (3)° N4A—C5A—C7B—C8A and -175.5 (2)° N4A—C5A—C7B—C8A torsion angles quantify this difference.

Hydrogen-bonding interactions usually appear to play a key role in the crystal packing of oxadiazinanones (Szczepura et al., 2004). However, it may be that the optimal crystal packing simply happens to yield an arrangement of molecules which are suggestive of a hydrogen bonding motif. That is packing forces other than formation of the weak H-bonding fortuitously lead to the motif. In the title compound, the 2.83 Å N3A—O17B and 2.89 Å N3B—O17A donor to acceptor separations are large enough to support only weak, if any, hydrogen bonding (Fig 4.). This interaction is further illustrated in the Jmol enhanced figure (Fig. 5).

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).

S2. Experimental

The title compound was prepared as previously reported (Dore et al. (2006)).

S3. Refinement

All non-H atoms were refined anisotropically without disorder. All H atoms were initially identified through difference Fourier syntheses then removed and included in the refinement in the riding-model approximation (C–H = 0.95, 0.98, 0.99 and 1.00 Å for Ar–H, CH₃ and CH₂ and CH; N–H = 0.88 Å; U_iso(H) = 1.2Ueq(C) except for methyl groups, where U_iso(H) = 1.5Ueq(C)). In the absence of significant anomalous scattering effects, Friedel pairs were merged.

Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); 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).

Figures

	Fig. 1. The molecular structure of compound (I), with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A Mercury view of the asymmetric unit of (I) highlighting the 2.83 Å N3A—O17B and 2.89 Å N3B—O17A donor to acceptor separations which support only weak, if any, hydrogen bonding.
	Fig. 3. A Mercury overlay of the two independent molecules in the asymmetric unit of (I) with H atoms shown in light blue.
	Fig. 4. A Mercury overlay of the two independent molecules in the asymmetric unit of (I) with one molecule shown in blue and one shown in violet.
	Fig. 5. Jmol enhanced figure of I. The default view shows the basic unit-cell contents. The pair of molecules forming the asymmetric unit and the putative H-bonding pair of molecules may be highlighted when viewing the active enhanced figure.

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

Crystal data

C13H18N2O2	F(000) = 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 = 2.3–30.5°
b = 11.4974 (17) Å	µ = 0.09 mm^−1
c = 22.600 (3) Å	T = 100 K
V = 2505.5 (6) Å^3	Block, colourless
Z = 8	0.43 × 0.23 × 0.23 mm

Data collection

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

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.060	w = 1/[σ^2(Fo^2) + (0.0413P)^2 + 1.6549P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.133	(Δ/σ)max < 0.001
S = 1.32	Δρmax = 0.37 e Å^−3
3499 reflections	Δρmin = −0.25 e Å^−3
307 parameters

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.

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

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)