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

Addison, L.D.; Dore, D.D.; Hitchcock, S.R.; Ferrence, G.M.

doi:10.1107/S1600536808013056

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages o1040-o1041

doi:10.1107/S1600536808013056

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

Lacey D. Addison,^a Delvis D. Dore,^a Shawn R. Hitchcock ^a and Gregory M. Ferrence ^a ^*

^aCB 4160, Department of Chemistry, Illinois State University, Normal, IL 61790, USA
^*Correspondence e-mail: ferrence@illinoisstate.edu

(Received 1 May 2008; accepted 2 May 2008; online 10 May 2008)

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.

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_r = 234.29
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.060
wR(F²) = 0.133
S = 1.32
3499 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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

Supporting information

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

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

checkCIF report

Comment top

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 top

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 top

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

Computing details top

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 top

	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 top

Crystal data top

C₁₃H₁₈N₂O₂	F(000) = 1008
M_r = 234.29	D_x = 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) Å³	Block, colourless
Z = 8	0.43 × 0.23 × 0.23 mm

Data collection top

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

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.060	w = 1/[σ²(F_o²) + (0.0413P)² + 1.6549P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.133	(Δ/σ)_max < 0.001
S = 1.32	Δρ_max = 0.37 e Å⁻³
3499 reflections	Δρ_min = −0.25 e Å⁻³
307 parameters

Crystal data top

C₁₃H₁₈N₂O₂	V = 2505.5 (6) Å³
M_r = 234.29	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.6423 (14) Å	µ = 0.09 mm⁻¹
b = 11.4974 (17) Å	T = 100 K
c = 22.600 (3) Å	0.43 × 0.23 × 0.23 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3499 independent reflections
Absorption correction: multi-scan SADABS in SAINT-Plus (Bruker, 2003)	3403 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.981	R_int = 0.041
25602 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.32	Δρ_max = 0.37 e Å⁻³
3499 reflections	Δρ_min = −0.25 e Å⁻³
307 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₃H₁₈N₂O₂
M_r	234.29
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	9.6423 (14), 11.4974 (17), 22.600 (3)
V (Å³)	2505.5 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.43 × 0.23 × 0.23

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan SADABS in SAINT-Plus (Bruker, 2003)
T_min, T_max	0.965, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	25602, 3499, 3403
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.133, 1.32
No. of reflections	3499
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.25

Computer programs: SMART (Bruker, 2003), SAINT-Plus (Bruker, 2003), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999) and publCIF (Westrip, 2008).

Selected geometric parameters (Å, º) top

C2A—N3A	1.340 (4)	C2B—N3B	1.346 (4)

C14A—N4A—C5A—C7A	155.5 (2)	C14B—N4B—C5B—C7B	159.1 (2)

Acknowledgements

This material is based upon work supported by the US National Science Foundation (CHE-0348158 to GMF) and the American Chemical Society Petroleum Research Fund (to SRH & GMF). GMF thanks Adam Beitelman (ISU) and Matthias Zeller, Youngstown State University Structure & Chemical Instrumentation Facility, for the data collection and useful discussions. The diffractometer was funded by NSF grant 0087210, Ohio Board of Regents grant CAP-491, and YSU.

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