2-N-Benzyl-2,6-dide-oxy-2,6-imino-3,4-O-isopropyl-idene-3-C-methyl-d-allono-nitrile.

X-ray crystallography firmly established the relative stereochemistry of the title compound, C(17)H(22)N(2)O(3). The absolute configuration was determined by use of 2-C-methyl-d-ribonolactone as the starting material. The compound exists as O-H⋯N hydrogen-bonded chains of mol-ecules running parallel to the a-axis.

Related literature

For 2-C-methyl sugar lactones and their use in synthesis, see: da Cruz et al. (2011 ▶); Best et al. (2010 ▶); da Cruz & Horne (2008 ▶6); Booth et al. (2008 ▶); Hotchkiss, Soengas et al. (2007 ▶); Hotchkiss, Kato et al. (2007 ▶); Hotchkiss et al. (2006 ▶); Sowden & Strobach (1960 ▶). For the biological activity of polyhy­droxy­lated piperidines, see: Nash et al. (2011 ▶); Watson et al. (2001 ▶). For the extinction correction, see: Larson (1970 ▶). For the temperature controller, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C17H22N2O3

M = 302.37

Orthorhombic,

a = 8.5647 (3) Å

b = 10.0019 (4) Å

c = 18.7031 (7) Å

V = 1602.17 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.25 × 0.25 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.96, T max = 0.98

7953 measured reflections

2082 independent reflections

1808 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.106

S = 0.97

2082 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.22 e Å−3

Data collection: COLLECT (Nonius, 2001 ▶).; cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/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/S1600536812016273/lh5456sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016273/lh5456Isup2.hkl

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

C17H22N2O3	F(000) = 648
Mr = 302.37	Dx = 1.253 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1959 reflections
a = 8.5647 (3) Å	θ = 5–27°
b = 10.0019 (4) Å	µ = 0.09 mm−1
c = 18.7031 (7) Å	T = 150 K
V = 1602.17 (10) Å3	Block, colourless
Z = 4	0.25 × 0.25 × 0.20 mm

Nonius KappaCCD diffractometer	1808 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ω scans	θmax = 27.5°, θmin = 5.2°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −11→11
Tmin = 0.96, Tmax = 0.98	k = −12→12
7953 measured reflections	l = −24→24
2082 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041	Method = Modified Sheldrick w = 1/[σ2(F2) + (0.07P)2 + 0.23P], where P = (max(Fo2,0) + 2Fc2)/3
wR(F2) = 0.106	(Δ/σ)max = 0.0002994
S = 0.97	Δρmax = 0.22 e Å−3
2082 reflections	Δρmin = −0.22 e Å−3
200 parameters	Extinction correction: Larson (1970), Equation 22
0 restraints	Extinction coefficient: 280 (110)
Primary atom site location: structure-invariant direct methods

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	0.28415 (17)	0.66972 (14)	0.47877 (7)	0.0285
C2	0.3904 (2)	0.7319 (2)	0.52685 (10)	0.0240
C3	0.4656 (2)	0.62006 (19)	0.56970 (10)	0.0245
N4	0.58010 (19)	0.67473 (16)	0.62140 (8)	0.0237
C5	0.6509 (2)	0.5619 (2)	0.66204 (10)	0.0290
C6	0.7562 (2)	0.47284 (19)	0.61857 (10)	0.0252
C7	0.9075 (2)	0.5134 (2)	0.60165 (11)	0.0298
C8	1.0092 (3)	0.4276 (2)	0.56690 (11)	0.0356
C9	0.9612 (3)	0.2999 (2)	0.54895 (12)	0.0377
C10	0.8116 (3)	0.2586 (2)	0.56503 (13)	0.0377
C11	0.7094 (3)	0.3444 (2)	0.59975 (12)	0.0317
C12	0.4923 (2)	0.7579 (2)	0.67274 (10)	0.0258
C13	0.5940 (3)	0.8056 (2)	0.73119 (12)	0.0349
N14	0.6690 (3)	0.8455 (3)	0.77702 (12)	0.0563
C15	0.4085 (2)	0.8802 (2)	0.63836 (10)	0.0258
C16	0.3102 (2)	0.8340 (2)	0.57458 (10)	0.0251
O17	0.17610 (16)	0.77936 (14)	0.60920 (7)	0.0267
C18	0.1432 (2)	0.8661 (2)	0.66828 (11)	0.0322
O19	0.29237 (16)	0.92224 (14)	0.68874 (8)	0.0293
C20	0.0777 (3)	0.7836 (3)	0.72865 (12)	0.0435
C21	0.0377 (3)	0.9798 (3)	0.64619 (15)	0.0503
C22	0.5170 (3)	0.9967 (2)	0.62255 (12)	0.0337
H21	0.4744	0.7726	0.4999	0.0256*
H31	0.5218	0.5592	0.5364	0.0293*
H32	0.3838	0.5684	0.5958	0.0277*
H51	0.5641	0.5120	0.6821	0.0339*
H52	0.7138	0.6041	0.7009	0.0357*
H71	0.9426	0.5985	0.6148	0.0359*
H81	1.1119	0.4591	0.5562	0.0416*
H91	1.0304	0.2415	0.5259	0.0458*
H101	0.7821	0.1690	0.5530	0.0463*
H111	0.6056	0.3166	0.6118	0.0379*
H121	0.4100	0.7095	0.6953	0.0311*
H161	0.2829	0.9145	0.5454	0.0290*
H203	0.0584	0.8381	0.7698	0.0637*
H202	−0.0209	0.7457	0.7123	0.0635*
H201	0.1521	0.7143	0.7417	0.0639*
H211	0.0220	1.0417	0.6876	0.0718*
H212	−0.0621	0.9372	0.6318	0.0712*
H213	0.0838	1.0319	0.6067	0.0702*
H223	0.4563	1.0631	0.5969	0.0499*
H222	0.6019	0.9635	0.5928	0.0502*
H221	0.5578	1.0406	0.6665	0.0511*
H11	0.2417	0.7301	0.4504	0.0457*

	U11	U22	U33	U12	U13	U23
O1	0.0278 (7)	0.0332 (7)	0.0244 (6)	0.0012 (7)	−0.0070 (6)	−0.0039 (6)
C2	0.0225 (10)	0.0293 (10)	0.0201 (8)	−0.0011 (8)	−0.0021 (8)	−0.0007 (8)
C3	0.0242 (9)	0.0254 (9)	0.0239 (9)	0.0009 (8)	−0.0016 (8)	0.0003 (8)
N4	0.0231 (8)	0.0267 (8)	0.0215 (7)	0.0005 (7)	−0.0002 (7)	−0.0002 (7)
C5	0.0277 (10)	0.0346 (11)	0.0249 (9)	0.0025 (9)	−0.0021 (8)	0.0032 (9)
C6	0.0253 (9)	0.0272 (10)	0.0233 (9)	0.0004 (8)	−0.0041 (8)	0.0050 (8)
C7	0.0295 (10)	0.0318 (10)	0.0281 (10)	−0.0015 (9)	−0.0036 (9)	0.0040 (9)
C8	0.0264 (11)	0.0433 (12)	0.0370 (11)	0.0009 (10)	0.0014 (9)	0.0064 (10)
C9	0.0368 (12)	0.0367 (12)	0.0397 (12)	0.0081 (10)	0.0054 (10)	0.0025 (10)
C10	0.0386 (12)	0.0288 (10)	0.0457 (12)	0.0000 (10)	−0.0020 (11)	−0.0007 (10)
C11	0.0254 (10)	0.0320 (10)	0.0377 (11)	−0.0020 (10)	−0.0031 (9)	0.0022 (9)
C12	0.0202 (9)	0.0347 (10)	0.0226 (8)	−0.0004 (9)	−0.0014 (8)	−0.0006 (8)
C13	0.0287 (10)	0.0480 (13)	0.0280 (10)	0.0089 (10)	−0.0025 (9)	−0.0087 (10)
N14	0.0397 (12)	0.0796 (16)	0.0496 (13)	0.0170 (13)	−0.0156 (10)	−0.0290 (13)
C15	0.0225 (9)	0.0295 (10)	0.0254 (9)	−0.0005 (9)	0.0015 (8)	−0.0028 (8)
C16	0.0233 (9)	0.0274 (9)	0.0246 (9)	0.0006 (8)	−0.0010 (7)	0.0000 (8)
O17	0.0214 (7)	0.0322 (7)	0.0266 (7)	−0.0012 (6)	0.0021 (6)	−0.0085 (6)
C18	0.0240 (10)	0.0411 (12)	0.0314 (11)	0.0006 (9)	−0.0023 (9)	−0.0138 (9)
O19	0.0219 (7)	0.0362 (8)	0.0297 (7)	−0.0004 (6)	0.0010 (6)	−0.0104 (6)
C20	0.0300 (12)	0.0660 (16)	0.0346 (11)	−0.0147 (12)	0.0082 (10)	−0.0152 (12)
C21	0.0372 (13)	0.0574 (16)	0.0563 (15)	0.0182 (13)	−0.0146 (12)	−0.0231 (13)
C22	0.0346 (11)	0.0305 (10)	0.0362 (11)	−0.0075 (10)	0.0036 (10)	−0.0040 (9)

O1—C2	1.422 (2)	C11—H111	0.958
O1—H11	0.882	C12—C13	1.477 (3)
C2—C3	1.519 (3)	C12—C15	1.557 (3)
C2—C16	1.521 (3)	C12—H121	0.954
C2—H21	0.968	C13—N14	1.143 (3)
C3—N4	1.482 (2)	C15—C16	1.531 (3)
C3—H31	0.994	C15—O19	1.433 (2)
C3—H32	0.998	C15—C22	1.519 (3)
N4—C5	1.490 (2)	C16—O17	1.427 (2)
N4—C12	1.477 (2)	C16—H161	0.999
C5—C6	1.506 (3)	O17—C18	1.433 (2)
C5—H51	0.971	C18—O19	1.447 (2)
C5—H52	0.998	C18—C20	1.507 (3)
C6—C7	1.394 (3)	C18—C21	1.510 (3)
C6—C11	1.391 (3)	C20—H203	0.958
C7—C8	1.385 (3)	C20—H202	0.975
C7—H71	0.935	C20—H201	0.972
C8—C9	1.383 (3)	C21—H211	1.000
C8—H81	0.956	C21—H212	0.992
C9—C10	1.380 (4)	C21—H213	0.987
C9—H91	0.937	C22—H223	0.971
C10—C11	1.387 (3)	C22—H222	0.974
C10—H101	0.958	C22—H221	0.995
C2—O1—H11	110.2	N4—C12—H121	112.2
O1—C2—C3	106.45 (16)	C13—C12—H121	105.8
O1—C2—C16	112.06 (16)	C15—C12—H121	103.9
C3—C2—C16	112.12 (15)	C12—C13—N14	177.7 (2)
O1—C2—H21	109.3	C12—C15—C16	109.79 (16)
C3—C2—H21	105.6	C12—C15—O19	106.20 (15)
C16—C2—H21	111.0	C16—C15—O19	102.67 (15)
C2—C3—N4	110.68 (15)	C12—C15—C22	113.61 (16)
C2—C3—H31	109.0	C16—C15—C22	114.56 (16)
N4—C3—H31	108.3	O19—C15—C22	109.11 (16)
C2—C3—H32	110.0	C15—C16—C2	114.30 (16)
N4—C3—H32	109.6	C15—C16—O17	101.79 (14)
H31—C3—H32	109.2	C2—C16—O17	111.85 (16)
C3—N4—C5	108.84 (15)	C15—C16—H161	108.1
C3—N4—C12	107.17 (15)	C2—C16—H161	109.1
C5—N4—C12	107.60 (14)	O17—C16—H161	111.5
N4—C5—C6	114.61 (15)	C16—O17—C18	106.03 (14)
N4—C5—H51	105.9	O17—C18—O19	105.37 (15)
C6—C5—H51	111.3	O17—C18—C20	108.63 (18)
N4—C5—H52	105.7	O19—C18—C20	110.04 (17)
C6—C5—H52	108.7	O17—C18—C21	111.28 (18)
H51—C5—H52	110.5	O19—C18—C21	107.97 (18)
C5—C6—C7	120.47 (18)	C20—C18—C21	113.3 (2)
C5—C6—C11	120.68 (19)	C18—O19—C15	108.96 (14)
C7—C6—C11	118.6 (2)	C18—C20—H203	110.8
C6—C7—C8	120.7 (2)	C18—C20—H202	107.5
C6—C7—H71	120.2	H203—C20—H202	108.8
C8—C7—H71	119.0	C18—C20—H201	109.6
C7—C8—C9	120.0 (2)	H203—C20—H201	108.5
C7—C8—H81	118.2	H202—C20—H201	111.7
C9—C8—H81	121.8	C18—C21—H211	109.6
C8—C9—C10	120.0 (2)	C18—C21—H212	105.4
C8—C9—H91	120.0	H211—C21—H212	111.2
C10—C9—H91	120.1	C18—C21—H213	111.3
C9—C10—C11	120.2 (2)	H211—C21—H213	107.9
C9—C10—H101	118.3	H212—C21—H213	111.6
C11—C10—H101	121.5	C15—C22—H223	107.1
C6—C11—C10	120.5 (2)	C15—C22—H222	107.8
C6—C11—H111	118.4	H223—C22—H222	110.5
C10—C11—H111	121.1	C15—C22—H221	113.1
N4—C12—C13	111.28 (16)	H223—C22—H221	107.1
N4—C12—C15	114.13 (15)	H222—C22—H221	111.1
C13—C12—C15	108.91 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H222···O1i	0.97	2.45	3.405 (3)	167
O1—H11···N4ii	0.88	2.15	2.997 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H11⋯N4i	0.88	2.15	2.997 (3)	161

Symmetry code: (i) .