N-Benzyl-3,5-dide-oxy-3,5-imino-1,2-O-isopropyl-idene-β-l-lyxofuran-ose.

X-ray crystallography confirmed the formation, structure and relative stereochemistry of the title compound, C(15)H(19)NO(3), which contains a sterically congested four-membered azetidine ring system. The absolute configuration was determined by the use of l-arabinose as the starting material.

Related literature

For related literature on azetidines, see: Krämer et al. (1997 ▶); Michaud et al. (1997a ▶,b ▶); Dekaris & Reissig (2010 ▶); Soengas et al. (2011 ▶); Jenkinson et al. (2011 ▶); Lenagh-Snow et al. (2011 ▶, 2012 ▶); Lee et al. (2012 ▶). For related literature on imino­sugars, see: Asano et al. (2000 ▶); Watson et al. (2001 ▶). For details of the cryostat, see: Cosier & Glazer (1986 ▶). For details of hydrogen refinement, see: Cooper et al. (2010 ▶). For references to the Chebychev polynomial, see: Prince (1982 ▶); Watkin (1994 ▶).

Experimental

Crystal data

C15H19NO3

M = 261.32

Monoclinic,

a = 9.1674 (2) Å

b = 5.7551 (1) Å

c = 13.1112 (3) Å

β = 106.9544 (8)°

V = 661.67 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.24 × 0.23 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.94, T max = 0.99

13110 measured reflections

1638 independent reflections

1544 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.087

S = 0.94

1638 reflections

172 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: COLLECT (Nonius, 2001 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812030656/lh5500sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030656/lh5500Isup2.hkl

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

C15H19NO3	F(000) = 280
Mr = 261.32	Dx = 1.312 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1627 reflections
a = 9.1674 (2) Å	θ = 5–27°
b = 5.7551 (1) Å	µ = 0.09 mm−1
c = 13.1112 (3) Å	T = 150 K
β = 106.9544 (8)°	Plate, colourless
V = 661.67 (2) Å3	0.24 × 0.23 × 0.07 mm
Z = 2

Nonius KappaCCD diffractometer	1544 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
ω scans	θmax = 27.4°, θmin = 5.4°
Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997)	h = −11→11
Tmin = 0.94, Tmax = 0.99	k = −7→6
13110 measured reflections	l = −16→16
1638 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.087	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 22.1 34.0 17.6 5.07
S = 0.94	(Δ/σ)max = 0.0003286
1638 reflections	Δρmax = 0.17 e Å−3
172 parameters	Δρmin = −0.18 e Å−3
1 restraint

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1 K.

	x	y	z	Uiso*/Ueq
O1	0.09793 (13)	0.5625 (2)	0.84062 (10)	0.0269
C2	0.25050 (17)	0.6293 (3)	0.89568 (13)	0.0260
C3	0.35745 (18)	0.6618 (3)	0.82587 (13)	0.0262
N4	0.31206 (15)	0.5481 (3)	0.72006 (11)	0.0264
C5	0.45568 (19)	0.4116 (4)	0.74729 (15)	0.0318
C6	0.48402 (19)	0.4783 (3)	0.86494 (14)	0.0292
O7	0.42651 (14)	0.3113 (3)	0.92411 (10)	0.0319
C8	0.31601 (19)	0.4200 (3)	0.96665 (14)	0.0284
O9	0.19278 (13)	0.2728 (3)	0.96037 (10)	0.0313
C10	0.07349 (18)	0.3246 (3)	0.86343 (14)	0.0274
C11	0.0820 (2)	0.1650 (3)	0.77364 (14)	0.0306
C12	−0.07829 (19)	0.3058 (4)	0.88768 (15)	0.0333
C13	0.2813 (2)	0.6967 (3)	0.62624 (14)	0.0309
C14	0.2617 (2)	0.5526 (4)	0.52659 (14)	0.0288
C15	0.3343 (2)	0.6152 (4)	0.45124 (14)	0.0320
C16	0.3150 (2)	0.4828 (4)	0.35950 (14)	0.0353
C17	0.2236 (2)	0.2866 (4)	0.34202 (15)	0.0346
C18	0.1518 (2)	0.2208 (4)	0.41731 (16)	0.0379
C19	0.1714 (2)	0.3523 (4)	0.50899 (15)	0.0343
H21	0.2489	0.7722	0.9365	0.0300*
H31	0.3962	0.8232	0.8266	0.0305*
H51	0.4416	0.2480	0.7305	0.0388*
H52	0.5313	0.4779	0.7148	0.0374*
H61	0.5871	0.5325	0.9042	0.0348*
H81	0.3666	0.4639	1.0430	0.0337*
H112	0.0678	0.0054	0.7931	0.0457*
H113	0.0002	0.2059	0.7092	0.0453*
H111	0.1807	0.1782	0.7612	0.0454*
H121	−0.0909	0.1489	0.9112	0.0506*
H123	−0.1589	0.3444	0.8220	0.0494*
H122	−0.0782	0.4156	0.9454	0.0507*
H132	0.1871	0.7872	0.6208	0.0373*
H131	0.3679	0.8067	0.6310	0.0372*
H151	0.3977	0.7507	0.4630	0.0386*
H161	0.3646	0.5290	0.3064	0.0422*
H171	0.2100	0.2000	0.2782	0.0423*
H181	0.0896	0.0854	0.4067	0.0458*
H191	0.1208	0.3077	0.5589	0.0420*

	U11	U22	U33	U12	U13	U23
O1	0.0214 (5)	0.0238 (6)	0.0331 (6)	0.0007 (5)	0.0041 (4)	0.0028 (5)
C2	0.0234 (7)	0.0239 (8)	0.0291 (7)	−0.0006 (6)	0.0051 (6)	−0.0014 (7)
C3	0.0234 (7)	0.0242 (8)	0.0299 (7)	−0.0018 (6)	0.0063 (6)	−0.0014 (6)
N4	0.0255 (6)	0.0246 (7)	0.0293 (7)	−0.0002 (6)	0.0081 (5)	−0.0014 (6)
C5	0.0287 (8)	0.0290 (9)	0.0385 (9)	0.0023 (7)	0.0108 (7)	−0.0040 (8)
C6	0.0225 (7)	0.0289 (9)	0.0349 (8)	−0.0002 (7)	0.0063 (6)	−0.0003 (7)
O7	0.0293 (6)	0.0270 (6)	0.0393 (6)	0.0054 (5)	0.0100 (5)	0.0060 (6)
C8	0.0251 (7)	0.0274 (9)	0.0313 (8)	0.0014 (7)	0.0058 (6)	0.0036 (7)
O9	0.0264 (6)	0.0333 (7)	0.0311 (6)	−0.0017 (5)	0.0034 (5)	0.0078 (5)
C10	0.0248 (7)	0.0257 (8)	0.0299 (8)	−0.0007 (7)	0.0054 (6)	0.0049 (7)
C11	0.0291 (8)	0.0254 (8)	0.0361 (8)	−0.0019 (7)	0.0077 (7)	0.0013 (7)
C12	0.0264 (7)	0.0366 (10)	0.0376 (8)	−0.0030 (8)	0.0105 (6)	0.0037 (8)
C13	0.0365 (8)	0.0249 (8)	0.0318 (8)	−0.0035 (8)	0.0106 (7)	−0.0007 (7)
C14	0.0268 (7)	0.0279 (9)	0.0307 (8)	0.0010 (7)	0.0066 (6)	−0.0015 (7)
C15	0.0289 (8)	0.0330 (10)	0.0326 (8)	−0.0028 (8)	0.0069 (6)	0.0022 (7)
C16	0.0307 (8)	0.0430 (12)	0.0337 (9)	0.0009 (8)	0.0116 (7)	0.0003 (8)
C17	0.0306 (8)	0.0374 (10)	0.0342 (8)	0.0042 (8)	0.0070 (7)	−0.0071 (8)
C18	0.0374 (9)	0.0322 (10)	0.0447 (10)	−0.0062 (8)	0.0129 (8)	−0.0080 (9)
C19	0.0357 (9)	0.0317 (10)	0.0379 (9)	−0.0066 (8)	0.0147 (7)	−0.0034 (8)

O1—C2	1.4271 (19)	C11—H112	0.972
O1—C10	1.433 (2)	C11—H113	0.981
C2—C3	1.535 (2)	C11—H111	0.967
C2—C8	1.534 (2)	C12—H121	0.972
C2—H21	0.984	C12—H123	0.983
C3—N4	1.480 (2)	C12—H122	0.985
C3—C6	1.542 (2)	C13—C14	1.513 (2)
C3—H31	0.994	C13—H132	0.993
N4—C5	1.484 (2)	C13—H131	1.003
N4—C13	1.457 (2)	C14—C15	1.390 (2)
C5—C6	1.536 (2)	C14—C19	1.399 (3)
C5—H51	0.967	C15—C16	1.391 (3)
C5—H52	0.990	C15—H151	0.957
C6—O7	1.429 (2)	C16—C17	1.385 (3)
C6—H61	0.986	C16—H161	0.974
O7—C8	1.435 (2)	C17—C18	1.389 (3)
C8—O9	1.395 (2)	C17—H171	0.950
C8—H81	1.005	C18—C19	1.387 (3)
O9—C10	1.4456 (19)	C18—H181	0.952
C10—C11	1.513 (3)	C19—H191	0.941
C10—C12	1.519 (2)
C2—O1—C10	109.99 (13)	O9—C10—C12	107.79 (14)
O1—C2—C3	115.67 (13)	O1—C10—C12	108.68 (15)
O1—C2—C8	104.34 (14)	C11—C10—C12	112.21 (15)
C3—C2—C8	104.59 (14)	C10—C11—H112	109.1
O1—C2—H21	109.4	C10—C11—H113	108.9
C3—C2—H21	109.7	H112—C11—H113	109.0
C8—C2—H21	113.1	C10—C11—H111	110.3
C2—C3—N4	116.83 (13)	H112—C11—H111	108.8
C2—C3—C6	105.56 (14)	H113—C11—H111	110.7
N4—C3—C6	89.27 (13)	C10—C12—H121	109.5
C2—C3—H31	113.4	C10—C12—H123	107.6
N4—C3—H31	115.1	H121—C12—H123	111.0
C6—C3—H31	113.9	C10—C12—H122	108.6
C3—N4—C5	91.22 (12)	H121—C12—H122	109.0
C3—N4—C13	117.65 (15)	H123—C12—H122	111.1
C5—N4—C13	116.97 (14)	N4—C13—C14	110.62 (16)
N4—C5—C6	89.30 (13)	N4—C13—H132	108.6
N4—C5—H51	114.2	C14—C13—H132	110.1
C6—C5—H51	116.3	N4—C13—H131	111.3
N4—C5—H52	112.1	C14—C13—H131	107.0
C6—C5—H52	113.7	H132—C13—H131	109.2
H51—C5—H52	109.9	C13—C14—C15	120.71 (17)
C3—C6—C5	86.95 (13)	C13—C14—C19	120.65 (16)
C3—C6—O7	106.25 (13)	C15—C14—C19	118.64 (17)
C5—C6—O7	113.33 (15)	C14—C15—C16	120.39 (18)
C3—C6—H61	118.1	C14—C15—H151	119.4
C5—C6—H61	117.3	C16—C15—H151	120.3
O7—C6—H61	112.3	C15—C16—C17	120.55 (17)
C6—O7—C8	109.39 (14)	C15—C16—H161	120.0
C2—C8—O7	107.62 (14)	C17—C16—H161	119.4
C2—C8—O9	105.91 (13)	C16—C17—C18	119.59 (18)
O7—C8—O9	111.33 (16)	C16—C17—H171	119.4
C2—C8—H81	113.1	C18—C17—H171	121.0
O7—C8—H81	108.9	C17—C18—C19	119.92 (19)
O9—C8—H81	110.0	C17—C18—H181	120.5
C8—O9—C10	108.58 (13)	C19—C18—H181	119.6
O9—C10—O1	104.85 (14)	C14—C19—C18	120.89 (17)
O9—C10—C11	111.18 (15)	C14—C19—H191	119.8
O1—C10—C11	111.77 (14)	C18—C19—H191	119.3

D—H···A	D—H	H···A	D···A	D—H···A
C11—H111···N4	0.97	2.58	3.266 (3)	128