6-Azido-6-de-oxy-α-l-galactose (6-azido-l-fucose) monohydrate.

Although 6-azido-6-de-oxy-l-galactose in aqueous solution is in equilibrium between the open-chain, furan-ose and pyran-ose forms, it crystallizes solely as 6-azido-6-de-oxy-α-l-galactopyran-ose monohydrate, C(6)H(11)N(3)O(5)·H(2)O, with the six-membered ring adopting a chair conformation. The structure exists as hydrogen-bonded chains, with each mol-ecule acting as a donor and acceptor of five hydrogen bonds. There are no unusual crystal packing features and the absolute configuration was determined from the use of 1-azido-1-de-oxy-d-galactitol as the starting material.

Related literature

For related literature see: Beadle et al. (1992 ▶); Izumori (2002 ▶, 2006 ▶); Granstrom et al. (2004 ▶); Sun et al. (2007 ▶); Levin (2002 ▶); Skytte (2002 ▶); Nakajima et al. (2004 ▶); Sui et al. (2005 ▶); Hossain et al. (2006 ▶); Kolb & Sharpless (2003 ▶); Chesterton et al. (2006 ▶); Görbitz (1999 ▶); Larson (1970 ▶); Prince (1982 ▶); Watkin (1994 ▶); Yoshihara et al. (2008 ▶).

Experimental

Crystal data

C6H11N3O5·H2O

M = 223.19

Orthorhombic,

a = 5.9687 (3) Å

b = 7.7395 (4) Å

c = 20.9768 (11) Å

V = 969.02 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 150 K

0.50 × 0.05 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶) T min = 0.86, T max = 0.99

7317 measured reflections

1296 independent reflections

792 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.073

S = 0.80

1095 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.36 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/S1600536808022563/lh2654sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022563/lh2654Isup2.hkl

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

C6H11N3O5·H2O	F000 = 472
Mr = 223.19	Dx = 1.530 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2018 reflections
a = 5.9687 (3) Å	θ = 5–27º
b = 7.7395 (4) Å	µ = 0.14 mm−1
c = 20.9768 (11) Å	T = 150 K
V = 969.02 (9) Å3	Plate, colourless
Z = 4	0.50 × 0.05 × 0.05 mm

Nonius KappaCCD diffractometer	792 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.053
T = 150 K	θmax = 27.4º
ω scans	θmin = 5.2º
Absorption correction: multi-scanDENZO/SCALEPACK (Otwinowski & Minor, 1997)	h = −7→7
Tmin = 0.86, Tmax = 0.99	k = −9→10
7317 measured reflections	l = −26→27
1296 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.033	w = 1/[σ2(F2)]
wR(F2) = 0.073	(Δ/σ)max = 0.0003
S = 0.80	Δρmax = 0.37 e Å−3
1095 reflections	Δρmin = −0.36 e Å−3
136 parameters	Extinction correction: None
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
O1	0.7366 (3)	0.6574 (2)	0.68646 (7)	0.0240
C2	0.8440 (4)	0.5120 (3)	0.65721 (11)	0.0207
C3	0.8824 (4)	0.3657 (4)	0.70492 (11)	0.0198
O4	1.0088 (3)	0.4176 (3)	0.76006 (7)	0.0239
C5	0.6592 (4)	0.2991 (4)	0.72879 (11)	0.0185
O6	0.7020 (3)	0.1614 (2)	0.77263 (7)	0.0218
C7	0.5141 (4)	0.2396 (3)	0.67315 (11)	0.0203
O8	0.6145 (3)	0.0996 (3)	0.64297 (8)	0.0276
O9	0.4833 (3)	0.3840 (2)	0.63098 (7)	0.0228
C10	0.6911 (4)	0.4467 (4)	0.60441 (11)	0.0223
C11	0.6234 (5)	0.5891 (4)	0.55904 (11)	0.0286
N12	0.5055 (4)	0.5214 (3)	0.50147 (10)	0.0336
N13	0.3088 (4)	0.4780 (4)	0.51035 (10)	0.0347
N14	0.1278 (4)	0.4350 (5)	0.51097 (11)	0.0585
O15	0.7358 (3)	0.5841 (3)	0.38440 (7)	0.0372
H21	0.9866	0.5468	0.6385	0.0251*
H31	0.9606	0.2684	0.6830	0.0246*
H51	0.5793	0.3928	0.7511	0.0236*
H71	0.3616	0.2056	0.6878	0.0253*
H101	0.7643	0.3512	0.5817	0.0281*
H111	0.7596	0.6432	0.5432	0.0344*
H112	0.5329	0.6774	0.5803	0.0343*
H152	0.6532	0.5377	0.4105	0.0561*
H11	0.8239	0.7312	0.6983	0.0373*
H41	1.1103	0.4866	0.7514	0.0381*
H151	0.6582	0.6044	0.3527	0.0563*
H81	0.5011	0.0423	0.6335	0.0441*
H62	0.5844	0.1468	0.7909	0.0334*

	U11	U22	U33	U12	U13	U23
O1	0.0231 (9)	0.0184 (10)	0.0306 (9)	0.0001 (9)	0.0005 (9)	−0.0023 (9)
C2	0.0192 (13)	0.0202 (16)	0.0226 (12)	0.0007 (13)	0.0055 (12)	−0.0010 (13)
C3	0.0164 (12)	0.0236 (18)	0.0193 (12)	0.0008 (13)	−0.0022 (11)	−0.0033 (13)
O4	0.0215 (9)	0.0256 (11)	0.0247 (9)	−0.0089 (9)	−0.0044 (8)	0.0023 (9)
C5	0.0192 (13)	0.0169 (16)	0.0193 (12)	−0.0005 (12)	0.0002 (11)	0.0020 (13)
O6	0.0193 (9)	0.0225 (11)	0.0236 (8)	0.0003 (9)	0.0017 (8)	0.0046 (10)
C7	0.0217 (13)	0.0184 (14)	0.0207 (13)	0.0012 (14)	−0.0002 (13)	−0.0003 (13)
O8	0.0269 (10)	0.0248 (11)	0.0310 (9)	−0.0028 (10)	−0.0001 (9)	−0.0065 (10)
O9	0.0194 (9)	0.0267 (11)	0.0223 (9)	−0.0011 (9)	0.0005 (8)	0.0043 (9)
C10	0.0218 (14)	0.0238 (16)	0.0213 (12)	0.0001 (13)	0.0043 (12)	0.0004 (13)
C11	0.0293 (15)	0.0334 (17)	0.0232 (13)	−0.0028 (16)	−0.0001 (12)	0.0066 (15)
N12	0.0253 (12)	0.0542 (19)	0.0213 (11)	−0.0009 (13)	0.0003 (11)	0.0049 (13)
N13	0.0364 (15)	0.0501 (19)	0.0174 (13)	0.0037 (14)	0.0003 (11)	0.0006 (13)
N14	0.0350 (16)	0.107 (3)	0.0336 (15)	−0.0156 (19)	0.0022 (14)	−0.0111 (19)
O15	0.0357 (10)	0.0476 (13)	0.0283 (9)	0.0078 (12)	0.0071 (9)	0.0092 (11)

O1—C2	1.433 (3)	C7—O9	1.437 (3)
O1—H11	0.812	C7—H71	0.997
C2—C3	1.529 (3)	O8—H81	0.834
C2—C10	1.522 (3)	O9—C10	1.444 (3)
C2—H21	0.975	C10—C11	1.511 (4)
C3—O4	1.438 (3)	C10—H101	0.982
C3—C5	1.514 (3)	C11—N12	1.493 (3)
C3—H31	0.999	C11—H111	0.973
O4—H41	0.828	C11—H112	0.978
C5—O6	1.431 (3)	N12—N13	1.235 (3)
C5—C7	1.524 (3)	N13—N14	1.130 (3)
C5—H51	0.986	O15—H152	0.820
O6—H62	0.807	O15—H151	0.825
C7—O8	1.391 (3)
C2—O1—H11	113.3	C5—C7—O9	108.0 (2)
O1—C2—C3	111.62 (19)	O8—C7—O9	112.39 (18)
O1—C2—C10	107.7 (2)	C5—C7—H71	111.2
C3—C2—C10	108.7 (2)	O8—C7—H71	109.2
O1—C2—H21	110.3	O9—C7—H71	106.2
C3—C2—H21	109.7	C7—O8—H81	100.0
C10—C2—H21	108.8	C7—O9—C10	112.87 (18)
C2—C3—O4	113.5 (2)	C2—C10—O9	110.25 (19)
C2—C3—C5	109.7 (2)	C2—C10—C11	112.1 (2)
O4—C3—C5	106.90 (18)	O9—C10—C11	104.97 (19)
C2—C3—H31	109.1	C2—C10—H101	109.6
O4—C3—H31	109.6	O9—C10—H101	108.5
C5—C3—H31	107.9	C11—C10—H101	111.2
C3—O4—H41	112.7	C10—C11—N12	112.3 (3)
C3—C5—O6	108.02 (19)	C10—C11—H111	107.7
C3—C5—C7	110.46 (18)	N12—C11—H111	105.6
O6—C5—C7	111.6 (2)	C10—C11—H112	111.8
C3—C5—H51	109.4	N12—C11—H112	110.7
O6—C5—H51	109.2	H111—C11—H112	108.4
C7—C5—H51	108.1	C11—N12—N13	114.9 (2)
C5—O6—H62	104.7	N12—N13—N14	171.9 (3)
C5—C7—O8	109.8 (2)	H152—O15—H151	106.5

D—H···A	D—H	H···A	D···A	D—H···A
O15—H152···N12	0.82	2.11	2.856 (4)	152
O1—H11···O4i	0.81	1.96	2.760 (4)	169
O4—H41···O6i	0.83	1.83	2.648 (4)	171
O15—H151···O4ii	0.83	2.19	2.989 (4)	163
O8—H81···O15iii	0.83	1.90	2.732 (4)	177
O6—H62···O1iv	0.81	1.98	2.755 (4)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H11⋯O4i	0.81	1.96	2.760 (4)	169
O4—H41⋯O6i	0.83	1.83	2.648 (4)	171
O15—H151⋯O4ii	0.83	2.19	2.989 (4)	163
O8—H81⋯O15iii	0.83	1.90	2.732 (4)	177
O6—H62⋯O1iv	0.81	1.98	2.755 (4)	162

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .