(5R,6S)-4-Isopropyl-5-methyl-6-phenyl-3-propanoyl-2H-1,3,4-oxadiazinan-2-one

Tailor, D.; Edler, K.L.; Casper, D.M.; Hitchcock, S.R.; Ferrence, G.M.

doi:10.1107/S1600536809022363

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages o1685-o1686

doi:10.1107/S1600536809022363

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(5R,6S)-4-Isopropyl-5-methyl-6-phenyl-3-propanoyl-2H-1,3,4-oxadiazinan-2-one

Dishant Tailor,^a Kate L. Edler,^a David M. Casper,^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 2 May 2009; accepted 11 June 2009; online 27 June 2009)

The title compound, C₁₆H₂₂N₂O₃, was synthesized during the course of a study on (1R,2S)-norephedrine-derived 1,3,4-oxadiazinan-2-ones. The conformation adopted by the isopropyl group is pseudo-axial relative to the oxadiazinan core. The allylic strain contributes to this conformational arrangement.

Related literature

For related structures and background, see: Casper, Blackburn et al. (2002 ); Casper, Burgeson et al. (2002 ); Casper & Hitchcock (2003 ); Evans et al. (1981 ); Ferrence et al. (2003 ), Hitchcock et al. (2001 ); Trepanier et al. (1968 ). The synthesis of the title compound is described by Hitchcock et al. (2004 ). For ring puckering analysis, see: Boeyens (1978 ); Cremer & Pople (1975 ); Spek (2009 ). For non-classical hydrogen bonding, see: Steiner (1996 ).

Experimental

Crystal data

C₁₆H₂₂N₂O₃
M_r = 290.36
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.8644 (3) Å
b = 10.8370 (5) Å
c = 21.2348 (10) Å
V = 1579.65 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 140 K
0.45 × 0.29 × 0.2 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003 ) T_min = 0.878, T_max = 0.983
16184 measured reflections
2263 independent reflections
2231 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.099
S = 1.18
2263 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1	0.95	2.40	2.737 (2)	101
C14—H14⋯O1	1.00	2.55	3.091 (2)	114
C15—H15A⋯N3	0.98	2.50	2.839 (2)	100
C5—H5⋯O20ⁱ	1.00	2.42	3.263 (2)	142
C16—H16B⋯O21ⁱ	0.98	2.40	3.380 (3)	175
C12—H12⋯O21ⁱ	0.95	2.35	3.243 (2)	156
C5—H5⋯O21ⁱ	1.00	2.40	3.283 (2)	147
C6—H6⋯O1ⁱⁱ	1.00	2.58	3.543 (2)	163
Symmetry codes: (i) x-1, y, z; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022363/zl2203sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022363/zl2203Isup2.hkl

checkCIF report

Comment top

The production of enantiomerically pure compounds has become increasingly important in the pharmaceutical industry. The high demand for a single enantiomer of a chiral intermediate has led to a wealth of methods for asymmetric synthesis (Hitchcock et al., 2004). While asymmetric catalysis and other methods have been functional in asymmetric synthesis, the important role of chiral auxiliaries in asymmetric synthesis is patent. Oxazolidin-2-ones, chiral auxiliaries first introduced by Evans et al. (Evans et al., 1981), have been of substance in areas of alkylation reactions, pericyclic reactions, and asymmetric aldol condensation reactions. Related, 1,3,4-oxadiazinan-2-one heterocycles have received little interest since their disclosure (Trepanier et al., 1968). It was not until recently that synthetic (Hitchcock et al., 2001) and conformational studies (Casper, Burgeson et al., 2002) of 1,3,4-oxadiazinan-2-one have been thoroughly performed.

Herein we report the X-ray structure of the N3-propanoyl acylated norephedrine-derived 1,3,4-oxadiazinan-2-one. The imide carbonyls adopt a syn-periplanar orientation, with an O21—C2—C17—O20 torsion angle of 23.67 (17)°. This result is consistent with those of previously reported N3 substituted oxadiazinan-2-ones (Casper, Blackburn et al., 2002; Casper, Burgeson et al., 2002; Ferrence et al., 2003). It is believed that in the oxadiazinaneone systems the syn-periplanar conformation arises from the lone pair repulsion interaction between the N4-nitrogen lone pair and the N3-carbonyl lone pair (Casper, Blackburn et al., 2002). However, in the case of the title compound, the repulsive interactions between the N3-substituent and the N4-isopropyl could also be held accountable for the syn-periplanar orientation. In fact, ring puckering analysis using PLATON (Spek, 2009; Cremer & Pople, 1975; Boeyens, 1978) indicates θ = 62.7 (2)° and Φ = 196.9 (2)° for the O1—C2—N3—N4—C5—C6 ring, which is consistent with a formal conformational assignment close to an idealized E₄ envelope with N4 being the flap apex. Such a conformation possesses a pseudo-axial C5-methyl group, a typical pseudo-equatorial C6-phenyl ring, and a typical pseudo-axial N4-iso-propyl group. The imide carbonyls, although not syn-parallel, indicate the existence of resonance delocalization due to their approximately planar conformation [torsion angle 23.67 (17)°]. Based on previous studies (Casper, Blackburn et al., 2002), the N3-substituent is held rigidly due to resonance interactions, while the N4-isopropyl group adopts a pseudoaxial orientation to relieve allylic strain on the system. Both intra- and inter-molecular non-classical H-bonding interactions exist. Those interactions shorter than 2.7 Å with a >90° D—H···A angle are shown in Table 1 (Steiner, 1996). It appears that such non-classical H-bonding interactions may constitute the dominant packing forces in this structure; however, evaluation of additional related structures will be necessary before any particular rational for these interactions is defensible.

Related literature top

For related structures and background, see: Casper, Blackburn et al. (2002); Casper, Burgeson et al. (2002); Casper & Hitchcock (2003); Evans et al. (1981); Ferrence et al. (2003), Hitchcock et al. (2001); Trepanier et al. (1968). The synthesis of the title compound is described by Hitchcock et al. (2004). For literature related to crystallographic analysis, see: Boeyens (1978); Cremer & Pople (1975); Spek (2009); Steiner (1996).

Experimental top

The title compound was synthesized by acylation of norephedrine derived 1,3,4-oxadiazinan-2-one using propanoyl (Hitchcock et al., 2004). Single crystals were grown by vapor diffusion of hexane into a methylene chloride solution of the title compound.

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); software used to prepare material for publication: WinGX (Farrugia, 1999) and publCIF (Westrip, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. J mol enhanced figure of the title compound. The default view shows a space-filling depiction of the asymmetric unit. Key torsion angles may be highlighted when viewing the active enhanced figure.

(5R,6S)-4-Isopropyl-5-methyl-6-phenyl-3-propanoyl-2H- 1,3,4-oxadiazinan-2-one top

Crystal data top

C₁₆H₂₂N₂O₃	F(000) = 624
M_r = 290.36	D_x = 1.221 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7989 reflections
a = 6.8644 (3) Å	θ = 2.7–30.4°
b = 10.8370 (5) Å	µ = 0.09 mm⁻¹
c = 21.2348 (10) Å	T = 140 K
V = 1579.65 (12) Å³	Needle, colourless
Z = 4	0.45 × 0.29 × 0.2 mm

Data collection top

Bruker SMART APEX CCD diffractometer	2263 independent reflections
Radiation source: sealed tube	2231 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003)	h = −9→9
T_min = 0.878, T_max = 0.983	k = −14→14
16184 measured reflections	l = −28→27

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.039	w = 1/[σ²(F_o²) + (0.0467P)² + 0.4577P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.099	(Δ/σ)_max < 0.001
S = 1.18	Δρ_max = 0.32 e Å⁻³
2263 reflections	Δρ_min = −0.21 e Å⁻³
190 parameters

Crystal data top

C₁₆H₂₂N₂O₃	V = 1579.65 (12) Å³
M_r = 290.36	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.8644 (3) Å	µ = 0.09 mm⁻¹
b = 10.8370 (5) Å	T = 140 K
c = 21.2348 (10) Å	0.45 × 0.29 × 0.2 mm

Data collection top

Bruker SMART APEX CCD diffractometer	2263 independent reflections
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003)	2231 reflections with I > 2σ(I)
T_min = 0.878, T_max = 0.983	R_int = 0.022
16184 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.18	Δρ_max = 0.32 e Å⁻³
2263 reflections	Δρ_min = −0.21 e Å⁻³
190 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
O1	0.75439 (18)	0.26491 (11)	0.44189 (6)	0.0196 (3)
C2	0.8863 (3)	0.34214 (16)	0.41773 (8)	0.0188 (3)
N3	0.8136 (2)	0.44240 (13)	0.38381 (7)	0.0178 (3)
N4	0.6120 (2)	0.47290 (13)	0.39003 (6)	0.0166 (3)
C5	0.5006 (2)	0.36039 (15)	0.37440 (7)	0.0165 (3)
H5	0.3593	0.3803	0.3796	0.020*
C6	0.5509 (2)	0.25838 (16)	0.42207 (8)	0.0163 (3)
H6	0.4683	0.2717	0.4602	0.020*
C7	0.5138 (3)	0.12801 (16)	0.39890 (8)	0.0187 (3)
C8	0.6638 (3)	0.05224 (17)	0.37881 (9)	0.0262 (4)
H8	0.7946	0.0806	0.3807	0.031*
C9	0.6234 (4)	−0.06520 (19)	0.35596 (10)	0.0326 (5)
H9	0.7270	−0.1166	0.3421	0.039*
C10	0.4342 (4)	−0.10773 (17)	0.35327 (9)	0.0320 (5)
H10	0.4073	−0.1883	0.3380	0.038*
C11	0.2841 (3)	−0.03214 (19)	0.37300 (10)	0.0315 (4)
H11	0.1535	−0.0608	0.3710	0.038*
C12	0.3230 (3)	0.08577 (17)	0.39586 (9)	0.0251 (4)
H12	0.2191	0.1373	0.4094	0.030*
C13	0.5331 (3)	0.32666 (16)	0.30550 (8)	0.0208 (3)
H13A	0.4971	0.3968	0.2788	0.031*
H13B	0.4523	0.2552	0.2946	0.031*
H13C	0.6706	0.3063	0.2988	0.031*
C14	0.5736 (3)	0.52506 (17)	0.45405 (8)	0.0225 (4)
H14	0.6017	0.4607	0.4865	0.027*
C15	0.7025 (3)	0.63686 (18)	0.46590 (10)	0.0310 (4)
H15A	0.8396	0.6123	0.4632	0.046*
H15B	0.6756	0.6700	0.5079	0.046*
H15C	0.6752	0.7002	0.4342	0.046*
C16	0.3600 (3)	0.5623 (2)	0.45843 (11)	0.0344 (5)
H16B	0.2776	0.4899	0.4511	0.052*
H16A	0.3318	0.6253	0.4266	0.052*
H16C	0.3334	0.5958	0.5004	0.052*
C17	0.9228 (2)	0.50008 (16)	0.33572 (8)	0.0195 (3)
C18	0.8239 (3)	0.60532 (17)	0.30136 (9)	0.0245 (4)
H18A	0.7224	0.5718	0.2730	0.029*
H18B	0.7594	0.6601	0.3323	0.029*
C19	0.9691 (3)	0.6793 (2)	0.26320 (11)	0.0344 (5)
H19C	0.9013	0.7465	0.2414	0.052*
H19B	1.0317	0.6254	0.2322	0.052*
H19A	1.0682	0.7139	0.2913	0.052*
O20	1.08450 (19)	0.46487 (14)	0.32269 (7)	0.0296 (3)
O21	1.05596 (18)	0.32428 (13)	0.42830 (6)	0.0266 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0168 (6)	0.0205 (6)	0.0214 (6)	−0.0011 (5)	−0.0033 (5)	0.0057 (5)
C2	0.0173 (7)	0.0213 (8)	0.0177 (7)	0.0005 (7)	−0.0004 (6)	0.0014 (6)
N3	0.0122 (6)	0.0190 (6)	0.0222 (7)	0.0004 (6)	0.0001 (5)	0.0033 (5)
N4	0.0121 (6)	0.0184 (6)	0.0194 (6)	0.0011 (5)	0.0013 (5)	−0.0003 (5)
C5	0.0144 (7)	0.0168 (7)	0.0183 (7)	0.0007 (6)	−0.0004 (6)	0.0017 (6)
C6	0.0126 (7)	0.0188 (7)	0.0174 (7)	−0.0009 (6)	0.0006 (6)	0.0014 (6)
C7	0.0216 (8)	0.0183 (7)	0.0163 (7)	−0.0009 (7)	0.0006 (6)	0.0015 (6)
C8	0.0260 (9)	0.0229 (8)	0.0297 (9)	0.0018 (8)	0.0019 (8)	−0.0018 (7)
C9	0.0420 (12)	0.0240 (9)	0.0318 (10)	0.0069 (9)	0.0038 (9)	−0.0036 (8)
C10	0.0539 (13)	0.0182 (8)	0.0239 (9)	−0.0074 (9)	−0.0026 (9)	−0.0011 (7)
C11	0.0337 (10)	0.0287 (10)	0.0322 (10)	−0.0126 (9)	−0.0017 (9)	0.0020 (8)
C12	0.0238 (9)	0.0230 (8)	0.0287 (9)	−0.0032 (8)	0.0008 (8)	0.0002 (7)
C13	0.0223 (8)	0.0226 (8)	0.0176 (7)	−0.0019 (8)	−0.0014 (6)	0.0010 (6)
C14	0.0281 (9)	0.0190 (7)	0.0203 (8)	−0.0011 (7)	0.0038 (7)	−0.0027 (6)
C15	0.0372 (11)	0.0242 (9)	0.0315 (9)	−0.0071 (8)	−0.0018 (9)	−0.0061 (8)
C16	0.0311 (10)	0.0337 (10)	0.0384 (11)	0.0030 (9)	0.0099 (9)	−0.0119 (9)
C17	0.0172 (7)	0.0208 (8)	0.0206 (7)	−0.0032 (7)	0.0000 (6)	0.0024 (6)
C18	0.0202 (8)	0.0239 (8)	0.0295 (9)	0.0003 (8)	0.0032 (7)	0.0086 (7)
C19	0.0281 (10)	0.0326 (10)	0.0424 (11)	−0.0031 (9)	0.0066 (9)	0.0167 (9)
O20	0.0183 (6)	0.0387 (8)	0.0318 (7)	0.0052 (6)	0.0061 (5)	0.0110 (6)
O21	0.0160 (6)	0.0325 (7)	0.0314 (7)	0.0020 (6)	−0.0018 (5)	0.0102 (6)

Geometric parameters (Å, º) top

O1—C2	1.336 (2)	C11—H11	0.9500
O1—C6	1.460 (2)	C12—H12	0.9500
C2—O21	1.202 (2)	C13—H13A	0.9800
C2—N3	1.396 (2)	C13—H13B	0.9800
N3—C17	1.413 (2)	C13—H13C	0.9800
N3—N4	1.4291 (19)	C14—C15	1.521 (3)
N4—C5	1.477 (2)	C14—C16	1.523 (3)
N4—C14	1.496 (2)	C14—H14	1.0000
C5—C13	1.524 (2)	C15—H15A	0.9800
C5—C6	1.538 (2)	C15—H15B	0.9800
C5—H5	1.0000	C15—H15C	0.9800
C6—C7	1.518 (2)	C16—H16B	0.9800
C6—H6	1.0000	C16—H16A	0.9800
C7—C8	1.384 (3)	C16—H16C	0.9800
C7—C12	1.389 (3)	C17—O20	1.206 (2)
C8—C9	1.390 (3)	C17—C18	1.515 (2)
C8—H8	0.9500	C18—C19	1.514 (3)
C9—C10	1.379 (3)	C18—H18A	0.9900
C9—H9	0.9500	C18—H18B	0.9900
C10—C11	1.381 (3)	C19—H19C	0.9800
C10—H10	0.9500	C19—H19B	0.9800
C11—C12	1.393 (3)	C19—H19A	0.9800

C2—O1—C6	124.62 (13)	C5—C13—H13A	109.5
O21—C2—O1	118.98 (16)	C5—C13—H13B	109.5
O21—C2—N3	124.62 (16)	H13A—C13—H13B	109.5
O1—C2—N3	116.34 (15)	C5—C13—H13C	109.5
C2—N3—C17	121.86 (14)	H13A—C13—H13C	109.5
C2—N3—N4	118.59 (14)	H13B—C13—H13C	109.5
C17—N3—N4	118.58 (14)	N4—C14—C15	110.40 (15)
N3—N4—C5	106.83 (12)	N4—C14—C16	108.99 (15)
N3—N4—C14	110.01 (13)	C15—C14—C16	109.78 (16)
C5—N4—C14	115.14 (13)	N4—C14—H14	109.2
N4—C5—C13	109.75 (13)	C15—C14—H14	109.2
N4—C5—C6	109.23 (13)	C16—C14—H14	109.2
C13—C5—C6	115.24 (14)	C14—C15—H15A	109.5
N4—C5—H5	107.4	C14—C15—H15B	109.5
C13—C5—H5	107.4	H15A—C15—H15B	109.5
C6—C5—H5	107.4	C14—C15—H15C	109.5
O1—C6—C7	107.41 (14)	H15A—C15—H15C	109.5
O1—C6—C5	111.69 (13)	H15B—C15—H15C	109.5
C7—C6—C5	114.71 (13)	C14—C16—H16B	109.5
O1—C6—H6	107.6	C14—C16—H16A	109.5
C7—C6—H6	107.6	H16B—C16—H16A	109.5
C5—C6—H6	107.6	C14—C16—H16C	109.5
C8—C7—C12	119.44 (17)	H16B—C16—H16C	109.5
C8—C7—C6	121.81 (16)	H16A—C16—H16C	109.5
C12—C7—C6	118.71 (15)	O20—C17—N3	120.94 (16)
C7—C8—C9	120.16 (19)	O20—C17—C18	122.72 (16)
C7—C8—H8	119.9	N3—C17—C18	116.33 (15)
C9—C8—H8	119.9	C19—C18—C17	111.18 (16)
C10—C9—C8	120.54 (19)	C19—C18—H18A	109.4
C10—C9—H9	119.7	C17—C18—H18A	109.4
C8—C9—H9	119.7	C19—C18—H18B	109.4
C9—C10—C11	119.44 (18)	C17—C18—H18B	109.4
C9—C10—H10	120.3	H18A—C18—H18B	108.0
C11—C10—H10	120.3	C18—C19—H19C	109.5
C10—C11—C12	120.46 (19)	C18—C19—H19B	109.5
C10—C11—H11	119.8	H19C—C19—H19B	109.5
C12—C11—H11	119.8	C18—C19—H19A	109.5
C7—C12—C11	119.96 (18)	H19C—C19—H19A	109.5
C7—C12—H12	120.0	H19B—C19—H19A	109.5
C11—C12—H12	120.0

C6—O1—C2—O21	−165.68 (17)	O1—C6—C7—C12	160.20 (15)
C6—O1—C2—N3	17.1 (2)	C5—C6—C7—C12	−75.0 (2)
O21—C2—N3—C17	29.6 (3)	C12—C7—C8—C9	−0.2 (3)
O1—C2—N3—C17	−153.40 (15)	C6—C7—C8—C9	−177.88 (17)
O21—C2—N3—N4	−161.87 (17)	C7—C8—C9—C10	−0.3 (3)
O1—C2—N3—N4	15.2 (2)	C8—C9—C10—C11	0.6 (3)
C2—N3—N4—C5	−55.15 (18)	C9—C10—C11—C12	−0.4 (3)
C17—N3—N4—C5	113.79 (15)	C8—C7—C12—C11	0.3 (3)
C2—N3—N4—C14	70.48 (18)	C6—C7—C12—C11	178.08 (16)
C17—N3—N4—C14	−120.58 (16)	C10—C11—C12—C7	0.0 (3)
N3—N4—C5—C13	−64.81 (16)	N3—N4—C14—C15	56.73 (18)
C14—N4—C5—C13	172.72 (14)	C5—N4—C14—C15	177.48 (15)
N3—N4—C5—C6	62.43 (16)	N3—N4—C14—C16	177.38 (15)
C14—N4—C5—C6	−60.04 (17)	C5—N4—C14—C16	−61.87 (18)
C2—O1—C6—C7	120.86 (16)	C2—N3—C17—O20	−0.7 (3)
C2—O1—C6—C5	−5.7 (2)	N4—N3—C17—O20	−169.21 (16)
N4—C5—C6—O1	−34.68 (18)	C2—N3—C17—C18	178.17 (16)
C13—C5—C6—O1	89.39 (17)	N4—N3—C17—C18	9.6 (2)
N4—C5—C6—C7	−157.20 (14)	O20—C17—C18—C19	−15.4 (3)
C13—C5—C6—C7	−33.1 (2)	N3—C17—C18—C19	165.80 (17)
O1—C6—C7—C8	−22.1 (2)	O21—C2—C17—O20	23.67 (17)
C5—C6—C7—C8	102.74 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.95	2.40	2.737 (2)	101
C14—H14···O1	1.00	2.55	3.091 (2)	114
C15—H15A···N3	0.98	2.50	2.839 (2)	100
C5—H5···O20ⁱ	1.00	2.42	3.263 (2)	142
C16—H16B···O21ⁱ	0.98	2.40	3.380 (3)	175
C12—H12···O21ⁱ	0.95	2.35	3.243 (2)	156
C5—H5···O21ⁱ	1.00	2.40	3.283 (2)	147
C6—H6···O1ⁱⁱ	1.00	2.58	3.543 (2)	163

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

Experimental details

Crystal data
Chemical formula	C₁₆H₂₂N₂O₃
M_r	290.36
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	140
a, b, c (Å)	6.8644 (3), 10.8370 (5), 21.2348 (10)
V (Å³)	1579.65 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.45 × 0.29 × 0.2

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS in SAINT-Plus; Bruker, 2003)
T_min, T_max	0.878, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	16184, 2263, 2231
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.099, 1.18
No. of reflections	2263
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.21

Computer programs: SMART (Bruker, 2003), SAINT-Plus (Bruker, 2003), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.95	2.40	2.737 (2)	100.5
C14—H14···O1	1.00	2.55	3.091 (2)	113.8
C15—H15A···N3	0.98	2.50	2.839 (2)	99.8
C5—H5···O20ⁱ	1.00	2.42	3.263 (2)	141.5
C16—H16B···O21ⁱ	0.98	2.40	3.380 (3)	174.9
C12—H12···O21ⁱ	0.95	2.35	3.243 (2)	156.4
C5—H5···O21ⁱ	1.00	2.40	3.283 (2)	146.5
C6—H6···O1ⁱⁱ	1.00	2.58	3.543 (2)	162.8

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

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 Youngstown State University Structure & Chemical Instrumentation Facility's Matthias Zeller for data collection and useful discussion. The diffractometer was funded by NSF grant 0087210, Ohio Board of Regents grant CAP-491, and YSU.

References

Boeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317–320. CrossRef Web of Science Google Scholar
Bruker (2003). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Casper, D. M., Blackburn, J. R., Maroules, C. D., Brady, T., Esken, J. M., Ferrence, G. M., Standard, J. M. & Hitchcock, S. R. (2002). J. Org. Chem. 67, 8871-8876. Web of Science CSD CrossRef PubMed CAS Google Scholar
Casper, D. M., Burgeson, J. R., Esken, J. M., Ferrence, G. M. & Hitchcock, S. R. (2002). Org. Lett. 4, 3739-3742. Web of Science CSD CrossRef PubMed CAS Google Scholar
Casper, D. M. & Hitchcock, S. R. (2003). Tetrahedron Asymmetry, 14, 517-521. Web of Science CrossRef CAS Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Evans, D. A., Bartolli, J. & Shih, T. L. (1981). J. Am. Chem. Soc. 103, 2127–2129. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Ferrence, G. M., Esken, J. M., Blackburn, J. R. & Hitchcock, S. R. (2003). Acta Cryst. E59, o212–o214. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hitchcock, S. R., Casper, D. M., Vaughn, J. F., Finefield, J. M., Ferrence, G. M. & Esken, J. M. (2004). J. Org. Chem. 69, 714-718. Web of Science CSD CrossRef PubMed CAS Google Scholar
Hitchcock, S. R., Nora, G. P., Casper, D. M., Squire, M. D., Maroules, C. D., Ferrence, G. M., Szczepura, L. F. & Standard, J. M. (2001). Tetrahedron, 57, 9789-9798. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Steiner, T. (1996). Cryst. Rev., 6, 1–57. CrossRef CAS Google Scholar
Trepanier, D. L., Elbe, J. N. & Harris, G. H. (1968). J. Med. Chem. 11, 357–361. CrossRef CAS PubMed Web of Science Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar