(4S,5R,6R)-Methyl 4-hydr-oxy-4,5-iso-propyl-idenedioxy-4,5,6,7-tetra-hydro-1,2,3-triazolo[1,5-a]pyridine-3-carboxyl-ate.

X-ray crystallography confirmed the structure of the title triazole, C(11)H(15)N(3)O(5), formed from a single-step reaction of a sugar azide with a brominated ylid. The absolute configuration was determined by the use of d-ribose as the starting material. The six-membered ring is in a half-chair conformation. The crystal structure exists as chains of O-H⋯O hydrogen-bonded moleclues running parallel to the b axis.

Related literature

For imino sugars, see: Asano et al. (2000 ▶); Watson et al. (2001 ▶). For sugar tetra­zoles, see: Brandstetter et al. (1995 ▶); Davis et al. (1995 ▶); Ermert et al. (1991 ▶). For sugar triazoles, see: Caravano et al. (2007 ▶); Krivopalov & Shkurko (2005 ▶); Krulle et al. (1997 ▶); Marco-Contelles & Rodriguez-Fernandez (2001 ▶, 2002 ▶); Oikonomakos (2002 ▶); Tatsuta et al. (1996 ▶). For related literature, see: Görbitz (1999 ▶); Larson (1970 ▶).

Experimental

Crystal data

C11H15N3O5

M = 269.26

Monoclinic,

a = 8.0587 (3) Å

b = 7.3797 (3) Å

c = 10.9785 (5) Å

β = 96.2740 (18)°

V = 648.99 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 150 K

0.60 × 0.15 × 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)

9525 measured reflections

1595 independent reflections

1219 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.082

S = 0.96

1595 reflections

173 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.31 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/S1600536809006357/lh2778sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006357/lh2778Isup2.hkl

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

C11H15N3O5	F(000) = 284
Mr = 269.26	Dx = 1.378 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1565 reflections
a = 8.0587 (3) Å	θ = 5–27°
b = 7.3797 (3) Å	µ = 0.11 mm−1
c = 10.9785 (5) Å	T = 150 K
β = 96.2740 (18)°	Plate, colourless
V = 648.99 (5) Å3	0.60 × 0.15 × 0.03 mm
Z = 2

Nonius KappaCCD diffractometer	1219 reflections with I > 2σ(I)
graphite	Rint = 0.059
ω scans	θmax = 27.5°, θmin = 5.2°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −10→10
Tmin = 0.82, Tmax = 1.00	k = −9→9
9525 measured reflections	l = −14→14
1595 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.037	Method = Modified Sheldrick w = 1/[σ2(F2) + (0.04P)2 + 0.06P], where P = [max(Fo2,0) + 2Fc2]/3
wR(F2) = 0.082	(Δ/σ)max = 0.0001
S = 0.97	Δρmax = 0.30 e Å−3
1595 reflections	Δρmin = −0.31 e Å−3
173 parameters	Extinction correction: Larson (1970), Equation 22
1 restraint	Extinction coefficient: 120 (30)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
O1	0.2044 (2)	0.3385 (2)	0.12370 (17)	0.0348
C2	0.3680 (3)	0.2921 (3)	0.0939 (2)	0.0259
C3	0.4700 (3)	0.4559 (3)	0.14365 (19)	0.0263
O4	0.3535 (2)	0.6018 (2)	0.12971 (16)	0.0369
C5	0.1853 (3)	0.5296 (3)	0.1071 (3)	0.0371
C6	0.1173 (3)	0.5757 (4)	−0.0230 (3)	0.0481
C7	0.0820 (4)	0.5983 (5)	0.2022 (3)	0.0711
C8	0.5404 (3)	0.4306 (3)	0.27502 (19)	0.0274
N9	0.5115 (2)	0.2809 (3)	0.33823 (15)	0.0314
N10	0.5960 (3)	0.2829 (4)	0.45255 (16)	0.0404
N11	0.6780 (2)	0.4367 (3)	0.46271 (17)	0.0393
C12	0.6470 (3)	0.5312 (3)	0.35555 (19)	0.0301
C13	0.7152 (3)	0.7105 (4)	0.3339 (2)	0.0347
O14	0.6759 (2)	0.7985 (3)	0.24224 (16)	0.0410
O15	0.8253 (2)	0.7650 (3)	0.42672 (17)	0.0493
C16	0.8993 (4)	0.9424 (5)	0.4125 (3)	0.0619
C17	0.4111 (3)	0.1253 (4)	0.2922 (2)	0.0340
C18	0.4225 (3)	0.1151 (3)	0.1552 (2)	0.0282
O19	0.3191 (2)	−0.0250 (2)	0.10143 (15)	0.0345
H21	0.3716	0.2823	0.0030	0.0326*
H31	0.5628	0.4800	0.0923	0.0335*
H62	0.1213	0.7081	−0.0306	0.0684*
H61	0.0013	0.5339	−0.0390	0.0679*
H63	0.1873	0.5166	−0.0791	0.0683*
H72	0.0760	0.7296	0.1946	0.1122*
H71	−0.0294	0.5466	0.1898	0.1121*
H73	0.1367	0.5658	0.2826	0.1119*
H163	0.9999	0.9506	0.4700	0.0913*
H162	0.9284	0.9553	0.3294	0.0911*
H161	0.8193	1.0353	0.4304	0.0913*
H172	0.2930	0.1423	0.3074	0.0432*
H171	0.4592	0.0151	0.3327	0.0435*
H181	0.5417	0.0915	0.1425	0.0336*
H191	0.3489	−0.1327	0.1166	0.0521*

	U11	U22	U33	U12	U13	U23
O1	0.0270 (8)	0.0198 (9)	0.0582 (11)	0.0004 (7)	0.0067 (7)	0.0020 (7)
C2	0.0241 (11)	0.0212 (11)	0.0325 (11)	0.0008 (10)	0.0032 (8)	−0.0010 (11)
C3	0.0298 (11)	0.0224 (12)	0.0259 (11)	0.0021 (10)	−0.0007 (9)	0.0011 (10)
O4	0.0340 (9)	0.0205 (9)	0.0524 (11)	0.0020 (8)	−0.0125 (7)	−0.0004 (8)
C5	0.0267 (12)	0.0178 (12)	0.0658 (17)	0.0013 (10)	0.0007 (11)	−0.0001 (12)
C6	0.0357 (13)	0.0268 (14)	0.0762 (19)	−0.0026 (12)	−0.0191 (13)	0.0064 (14)
C7	0.075 (2)	0.041 (2)	0.105 (3)	0.0097 (18)	0.0425 (19)	−0.0053 (19)
C8	0.0270 (11)	0.0247 (12)	0.0305 (11)	0.0084 (11)	0.0040 (9)	−0.0028 (11)
N9	0.0372 (10)	0.0314 (11)	0.0256 (9)	0.0035 (10)	0.0040 (8)	0.0024 (9)
N10	0.0491 (12)	0.0475 (14)	0.0241 (9)	0.0073 (12)	0.0023 (8)	0.0009 (11)
N11	0.0427 (11)	0.0465 (14)	0.0279 (10)	0.0110 (12)	−0.0003 (8)	−0.0067 (11)
C12	0.0294 (11)	0.0315 (14)	0.0283 (12)	0.0091 (10)	−0.0011 (9)	−0.0061 (11)
C13	0.0262 (11)	0.0346 (14)	0.0413 (14)	0.0068 (11)	−0.0055 (10)	−0.0129 (12)
O14	0.0382 (9)	0.0298 (10)	0.0524 (11)	0.0004 (9)	−0.0062 (8)	−0.0029 (10)
O15	0.0406 (10)	0.0451 (13)	0.0576 (11)	0.0030 (9)	−0.0157 (8)	−0.0195 (10)
C16	0.0454 (15)	0.0440 (19)	0.091 (2)	−0.0055 (16)	−0.0167 (14)	−0.0262 (18)
C17	0.0404 (13)	0.0262 (13)	0.0366 (13)	0.0005 (11)	0.0099 (10)	0.0045 (11)
C18	0.0313 (11)	0.0196 (12)	0.0335 (12)	0.0020 (10)	0.0030 (9)	0.0005 (10)
O19	0.0413 (9)	0.0137 (8)	0.0481 (10)	0.0003 (7)	0.0036 (7)	−0.0011 (7)

O1—C2	1.434 (3)	C8—C12	1.380 (3)
O1—C5	1.429 (3)	N9—N10	1.361 (3)
C2—C3	1.529 (3)	N9—C17	1.463 (3)
C2—C18	1.512 (3)	N10—N11	1.312 (3)
C2—H21	1.004	N11—C12	1.367 (3)
C3—O4	1.426 (3)	C12—C13	1.462 (4)
C3—C8	1.503 (3)	C13—O14	1.211 (3)
C3—H31	1.000	C13—O15	1.338 (3)
O4—C5	1.452 (3)	O15—C16	1.454 (4)
C5—C6	1.512 (4)	C16—H163	0.973
C5—C7	1.494 (4)	C16—H162	0.971
C6—H62	0.981	C16—H161	0.976
C6—H61	0.982	C17—C18	1.519 (3)
C6—H63	0.982	C17—H172	0.992
C7—H72	0.973	C17—H171	0.986
C7—H71	0.971	C18—O19	1.416 (3)
C7—H73	0.973	C18—H181	1.001
C8—N9	1.339 (3)	O19—H191	0.842
C2—O1—C5	107.18 (19)	C3—C8—C12	133.8 (2)
O1—C2—C3	101.66 (18)	N9—C8—C12	104.07 (19)
O1—C2—C18	109.52 (18)	C8—N9—N10	111.8 (2)
C3—C2—C18	113.92 (17)	C8—N9—C17	126.16 (18)
O1—C2—H21	111.8	N10—N9—C17	122.0 (2)
C3—C2—H21	109.8	N9—N10—N11	106.53 (19)
C18—C2—H21	110.0	N10—N11—C12	108.96 (19)
C2—C3—O4	103.68 (16)	C8—C12—N11	108.7 (2)
C2—C3—C8	112.1 (2)	C8—C12—C13	127.0 (2)
O4—C3—C8	111.83 (18)	N11—C12—C13	124.4 (2)
C2—C3—H31	110.2	C12—C13—O14	123.5 (2)
O4—C3—H31	109.2	C12—C13—O15	112.2 (2)
C8—C3—H31	109.6	O14—C13—O15	124.3 (3)
C3—O4—C5	109.44 (17)	C13—O15—C16	115.8 (2)
O4—C5—O1	104.75 (19)	O15—C16—H163	108.0
O4—C5—C6	108.3 (2)	O15—C16—H162	109.4
O1—C5—C6	111.5 (2)	H163—C16—H162	109.5
O4—C5—C7	109.7 (2)	O15—C16—H161	108.8
O1—C5—C7	107.8 (2)	H163—C16—H161	110.4
C6—C5—C7	114.3 (2)	H162—C16—H161	110.6
C5—C6—H62	107.0	N9—C17—C18	106.86 (19)
C5—C6—H61	109.7	N9—C17—H172	110.3
H62—C6—H61	109.7	C18—C17—H172	109.6
C5—C6—H63	108.6	N9—C17—H171	108.5
H62—C6—H63	111.3	C18—C17—H171	110.0
H61—C6—H63	110.4	H172—C17—H171	111.4
C5—C7—H72	107.7	C17—C18—C2	110.60 (19)
C5—C7—H71	110.2	C17—C18—O19	110.65 (19)
H72—C7—H71	110.0	C2—C18—O19	108.43 (17)
C5—C7—H73	108.6	C17—C18—H181	108.0
H72—C7—H73	109.7	C2—C18—H181	108.9
H71—C7—H73	110.5	O19—C18—H181	110.2
C3—C8—N9	122.1 (2)	C18—O19—H191	117.7

D—H···A	D—H	H···A	D···A	D—H···A
C3—H31···O19i	1.00	2.42	3.339 (4)	152
C16—H161···N10ii	0.98	2.59	3.567 (4)	174
O19—H191···O4iii	0.84	1.96	2.782 (4)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O19—H191⋯O4i	0.84	1.96	2.782 (4)	163

Symmetry code: (i) .