(4R)-4-(2-Allyl-2H-1,2,3-triazol-4-yl)-1,2-O-isopropyl-idene-l-threose.

X-ray crystallography unequivocally confirmed the structure of the title compound, C(12)H(17)N(3)O(4), as (4R)-4-(2-allyl-2H-1,2,3-triazol-4-yl)-1,2-O-isopropyl-idene-l-threose. The absolute configuration was determined by the use of d-glucorono-3,6-lactone as the starting material. The crystal structure consists of hydrogen-bonded chains of mol-ecules running parallel to the a axis. There are no unusual packing features.

Related literature

For related background information on the biotechnological inter­conversion of monosaccharides and other sugars, see: Izumori (2002 ▶, 2006 ▶); Granstrom et al. (2004 ▶); Yoshihara et al. (2008 ▶); Booth et al. (2008 ▶); Jenkinson, Booth, Gullapalli et al. (2008 ▶); Jenkinson, Booth, Yoshihara et al. (2008 ▶); Gullapalli et al. (2007 ▶); Jenkinson, Booth, Best et al. (2008 ▶). For related literature, see: Görbitz (1999 ▶).

Experimental

Crystal data

C12H17N3O4

M = 267.28

Orthorhombic,

a = 5.3959 (2) Å

b = 9.6233 (3) Å

c = 25.4532 (9) Å

V = 1321.69 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 150 K

0.30 × 0.20 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.82, T max = 1.00 (expected range = 0.817–0.997)

9466 measured reflections

1528 independent reflections

1194 reflections with I > 2σ(I)

R int = 0.096

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.098

S = 0.93

1528 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.33 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 datablocks global, I. DOI: 10.1107/S1600536808036416/lh2725sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036416/lh2725Isup2.hkl

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

C12H17N3O4	F000 = 568
Mr = 267.28	Dx = 1.343 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1500 reflections
a = 5.3959 (2) Å	θ = 5–26º
b = 9.6233 (3) Å	µ = 0.10 mm−1
c = 25.4532 (9) Å	T = 150 K
V = 1321.69 (8) Å3	Plate, colourless
Z = 4	0.30 × 0.20 × 0.03 mm

Nonius KappaCCD diffractometer	1194 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.096
T = 150 K	θmax = 26.0º
ω scans	θmin = 5.3º
Absorption correction: multi-scan(DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −6→6
Tmin = 0.82, Tmax = 1.00	k = −11→11
9466 measured reflections	l = −30→31
1528 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	w = 1/[σ2(F2) + (0.04P)2 + 0.59P], where P = [max(Fo2,0) + 2Fc2]/3
wR(F2) = 0.098	(Δ/σ)max = 0.0001
S = 0.93	Δρmax = 0.32 e Å−3
1528 reflections	Δρmin = −0.33 e Å−3
172 parameters	Extinction correction: None
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
O1	1.0189 (4)	0.60546 (19)	0.14662 (7)	0.0395
C2	1.0670 (5)	0.7244 (3)	0.17865 (11)	0.0366
C3	0.8174 (6)	0.8008 (3)	0.17938 (10)	0.0374
O4	0.6798 (4)	0.7427 (2)	0.13781 (7)	0.0436
C5	0.8248 (6)	0.6390 (3)	0.11107 (11)	0.0407
C6	0.9294 (7)	0.7022 (4)	0.06094 (12)	0.0579
C7	0.6697 (7)	0.5117 (4)	0.10209 (15)	0.0608
O8	0.7063 (4)	0.7727 (2)	0.22853 (7)	0.0394
C9	0.8362 (6)	0.6572 (3)	0.25347 (11)	0.0371
C10	1.1041 (5)	0.6779 (3)	0.23535 (11)	0.0371
O11	1.2131 (4)	0.7866 (2)	0.26506 (8)	0.0425
C12	0.7862 (6)	0.6641 (3)	0.31060 (11)	0.0359
N13	0.6792 (5)	0.5578 (2)	0.33594 (9)	0.0372
N14	0.6586 (5)	0.6032 (2)	0.38514 (9)	0.0372
N15	0.7386 (5)	0.7336 (2)	0.39351 (9)	0.0406
C16	0.8223 (6)	0.7724 (3)	0.34651 (11)	0.0396
C17	0.5321 (6)	0.5246 (3)	0.42598 (12)	0.0404
C18	0.2777 (6)	0.5809 (3)	0.43621 (12)	0.0439
C19	0.1964 (7)	0.6160 (3)	0.48272 (12)	0.0499
H21	1.2090	0.7805	0.1665	0.0468*
H31	0.8420	0.9045	0.1748	0.0468*
H61	0.7897	0.7321	0.0390	0.0897*
H62	1.0308	0.6330	0.0433	0.0901*
H63	1.0262	0.7815	0.0727	0.0903*
H73	0.5330	0.5360	0.0790	0.0953*
H72	0.7699	0.4402	0.0859	0.0956*
H71	0.6044	0.4809	0.1356	0.0950*
H91	0.7757	0.5674	0.2382	0.0502*
H101	1.1990	0.5896	0.2360	0.0485*
H161	0.8989	0.8595	0.3389	0.0499*
H171	0.5156	0.4288	0.4138	0.0506*
H172	0.6324	0.5300	0.4584	0.0502*
H181	0.1730	0.5914	0.4060	0.0573*
H192	0.0314	0.6524	0.4857	0.0646*
H191	0.3038	0.6046	0.5128	0.0648*
H111	1.3679	0.7927	0.2545	0.0633*

	U11	U22	U33	U12	U13	U23
O1	0.0413 (12)	0.0331 (10)	0.0440 (11)	0.0027 (10)	−0.0005 (10)	−0.0048 (9)
C2	0.0328 (14)	0.0335 (15)	0.0434 (16)	−0.0013 (13)	0.0025 (13)	−0.0016 (13)
C3	0.0372 (14)	0.0345 (14)	0.0406 (15)	0.0007 (14)	0.0016 (14)	0.0007 (13)
O4	0.0369 (10)	0.0492 (12)	0.0447 (11)	0.0076 (11)	−0.0044 (10)	−0.0066 (10)
C5	0.0407 (16)	0.0378 (15)	0.0436 (16)	0.0052 (15)	−0.0022 (15)	−0.0015 (13)
C6	0.070 (2)	0.058 (2)	0.0457 (18)	0.0116 (19)	0.0039 (18)	0.0051 (17)
C7	0.057 (2)	0.0484 (19)	0.077 (2)	−0.007 (2)	−0.013 (2)	−0.0080 (18)
O8	0.0321 (10)	0.0450 (11)	0.0411 (10)	0.0061 (10)	0.0042 (9)	0.0053 (9)
C9	0.0349 (15)	0.0313 (14)	0.0451 (17)	0.0007 (13)	−0.0013 (14)	0.0035 (12)
C10	0.0315 (15)	0.0367 (15)	0.0430 (16)	0.0022 (12)	0.0012 (13)	−0.0064 (14)
O11	0.0292 (10)	0.0498 (11)	0.0486 (11)	−0.0048 (10)	0.0023 (9)	−0.0075 (10)
C12	0.0324 (14)	0.0326 (13)	0.0427 (15)	0.0006 (13)	0.0015 (14)	0.0005 (12)
N13	0.0381 (13)	0.0328 (12)	0.0408 (13)	−0.0013 (12)	0.0040 (12)	−0.0010 (10)
N14	0.0380 (13)	0.0320 (12)	0.0415 (13)	−0.0020 (12)	0.0021 (12)	0.0009 (11)
N15	0.0456 (14)	0.0334 (12)	0.0429 (13)	−0.0006 (12)	0.0012 (11)	−0.0013 (11)
C16	0.0408 (15)	0.0332 (14)	0.0447 (16)	0.0013 (15)	0.0017 (14)	0.0009 (13)
C17	0.0420 (16)	0.0359 (15)	0.0433 (17)	0.0005 (14)	0.0062 (14)	0.0027 (14)
C18	0.0396 (17)	0.0435 (16)	0.0486 (17)	−0.0038 (15)	0.0027 (15)	0.0003 (15)
C19	0.0482 (18)	0.0462 (17)	0.0552 (19)	−0.0032 (18)	0.0095 (18)	−0.0042 (15)

O1—C2	1.429 (3)	C9—C12	1.481 (4)
O1—C5	1.421 (4)	C9—H91	1.003
C2—C3	1.535 (4)	C10—O11	1.419 (3)
C2—C10	1.524 (4)	C10—H101	0.992
C2—H21	0.987	O11—H111	0.879
C3—O4	1.409 (3)	C12—N13	1.340 (3)
C3—O8	1.414 (3)	C12—C16	1.400 (4)
C3—H31	1.013	N13—N14	1.331 (3)
O4—C5	1.439 (3)	N14—N15	1.344 (3)
C5—C6	1.522 (4)	N14—C17	1.456 (4)
C5—C7	1.501 (4)	N15—C16	1.332 (4)
C6—H61	0.982	C16—H161	0.954
C6—H62	0.972	C17—C18	1.498 (4)
C6—H63	0.973	C17—H171	0.977
C7—H73	0.972	C17—H172	0.988
C7—H72	0.968	C18—C19	1.307 (4)
C7—H71	0.969	C18—H181	0.959
O8—C9	1.459 (3)	C19—H192	0.960
C9—C10	1.531 (4)	C19—H191	0.967
C2—O1—C5	108.4 (2)	C10—C9—C12	117.5 (3)
O1—C2—C3	103.4 (2)	O8—C9—H91	109.4
O1—C2—C10	109.2 (2)	C10—C9—H91	107.6
C3—C2—C10	104.2 (2)	C12—C9—H91	111.1
O1—C2—H21	113.6	C9—C10—C2	101.5 (2)
C3—C2—H21	115.0	C9—C10—O11	109.1 (2)
C10—C2—H21	110.8	C2—C10—O11	110.0 (2)
C2—C3—O4	105.3 (2)	C9—C10—H101	111.8
C2—C3—O8	106.9 (2)	C2—C10—H101	109.6
O4—C3—O8	111.4 (2)	O11—C10—H101	114.1
C2—C3—H31	110.9	C10—O11—H111	106.3
O4—C3—H31	112.0	C9—C12—N13	121.1 (2)
O8—C3—H31	110.2	C9—C12—C16	130.5 (3)
C3—O4—C5	110.1 (2)	N13—C12—C16	108.3 (2)
O4—C5—O1	104.9 (2)	C12—N13—N14	103.8 (2)
O4—C5—C6	108.8 (2)	N13—N14—N15	115.4 (2)
O1—C5—C6	110.6 (3)	N13—N14—C17	122.7 (2)
O4—C5—C7	109.5 (3)	N15—N14—C17	121.5 (2)
O1—C5—C7	108.8 (2)	N14—N15—C16	103.2 (2)
C6—C5—C7	113.9 (3)	C12—C16—N15	109.3 (3)
C5—C6—H61	108.0	C12—C16—H161	125.6
C5—C6—H62	108.8	N15—C16—H161	125.1
H61—C6—H62	111.7	N14—C17—C18	111.5 (2)
C5—C6—H63	104.7	N14—C17—H171	107.9
H61—C6—H63	110.9	C18—C17—H171	108.2
H62—C6—H63	112.2	N14—C17—H172	108.2
C5—C7—H73	108.6	C18—C17—H172	109.7
C5—C7—H72	109.5	H171—C17—H172	111.4
H73—C7—H72	109.7	C17—C18—C19	123.9 (3)
C5—C7—H71	108.6	C17—C18—H181	116.0
H73—C7—H71	109.2	C19—C18—H181	120.0
H72—C7—H71	111.1	C18—C19—H192	118.6
C3—O8—C9	109.1 (2)	C18—C19—H191	119.2
O8—C9—C10	102.9 (2)	H192—C19—H191	122.2
O8—C9—C12	107.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H161···O1i	0.95	2.44	3.322 (4)	154
C17—H171···O4ii	0.98	2.46	3.362 (4)	154
O11—H111···O8iii	0.88	1.95	2.822 (4)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11—H111⋯O8i	0.88	1.95	2.822 (4)	170

Symmetry code: (i) .