4-Cyclo­propyl-1-(6′-de­oxy-1′,2′-O-iso­propyl­idene-α-d-gluco­furanos­yl)-1H-1,2,3-triazole

Zhang, Q.; He, P.; Zhou, G.; Yu, K.; Liu, H.

doi:10.1107/S1600536813021351

organic compounds

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ISSN: 2056-9890

Volume 69| Part 9| September 2013| Page o1386

doi:10.1107/S1600536813021351

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4-Cyclopropyl-1-(6′-deoxy-1′,2′-O-isopropylidene-α-D-glucofuranosyl)-1H-1,2,3-triazole

Qiurong Zhang,^a Peng He,^a Guangqiang Zhou,^a Kang Yu ^a and Hongmin Liu ^a ^*

^aNew Drug Reseach & Development Center, Zhengzhou Univresity, Zhengzhou 450001, People's Republic of China
^*Correspondence e-mail: zqr409@163.com

(Received 16 July 2013; accepted 31 July 2013; online 7 August 2013)

In the title compound, C₁₄H₂₁N₃O₅, the tetrahydrofuran ring adopts an envelope conformation with the C atom bearing the substituent as the flap. The pentafuranose ring adopts a twisted conformation about the C—C bond fusing the rings. The dihedral angle between these rings (all atoms), which are cis fused, is 72.89 (14)°. The cyclopropane ring is disordered over two orientations in a 0.576 (5):0.424 (5) ratio; the dihedral angles subtended to the triazole ring are 53.3 (11) and 46.6 (9)°, respectively. In the crystal, the molecules are linked by O—H⋯N and O—H⋯O hydrogen bonds, generating (001) sheets. A weak C—H⋯O interaction also occurs.

Related literature

For further synthetic details, see: Pradere et al. (2008 ). For background to 1,2,3-triazoles, see: Alvarez et al. (1994 ); Genin et al. (2000 ).

Experimental

Crystal data

C₁₄H₂₁N₃O₅
M_r = 311.34
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.5905 (3) Å
b = 8.7215 (3) Å
c = 20.7373 (7) Å
V = 1553.68 (9) Å³
Z = 4
Cu Kα radiation
μ = 0.85 mm⁻¹
T = 291 K
0.22 × 0.2 × 0.18 mm

Data collection

Bruker MWPC diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.835, T_max = 0.862
5692 measured reflections
2778 independent reflections
2503 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.113
S = 1.06
2778 reflections
220 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N3ⁱ	0.83 (2)	1.95 (2)	2.767 (3)	171 (3)
O5—H5⋯O3ⁱⁱ	0.82 (3)	2.02 (3)	2.821 (3)	164 (3)
C7—H7⋯O1ⁱⁱⁱ	0.93	2.59	3.496 (3)	165
Symmetry codes: (i) x, y+1, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z+1]$ ; (iii) x+1, y, z.

Data collection: FRAMBO (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813021351/hb7111sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813021351/hb7111Isup2.hkl

checkCIF report

Comment top

1,2,3-Triazoles have been shown to have various biological activities, such as anti-HIV (Alvarez et al., 1994) and antibacterial (Genin et al., 2000). C₁₄H₂₁N3_O5, the title compound (I), is a new 1,2,3-triazole. The nucleus of the molecule consists of one methylenedioxy rings, one 1,2,3-triazole ring, one cyclopropyl ring and one tetrahydrofuran ring (Fig. 1). The tetrahydrofuran ring fuses with one methylenedioxy ring,having the cis arrangement at the ring junctions and giving a V-shaped molecule.

The crystal packing, which features O—H···N hydrogen bonds (Table 1), is shown in Figure 2.

Related literature top

For further synthetic details, see: Pradere et al. (2008). For background to 1,2,3-triazoles, see: Alvarez et al. (1994); Genin et al. (2000).

Experimental top

The title compound (I) was synthesized from 6-azido-6-deoxy-1,2-O-isopropylidene-alpha -D-glucofuranose, whose starting material was D-glucose. The copper catalyzed reaction of 6-azido-6-deoxy-1,2-O-isopropylidene-alpha -D-glucofuranose(1 mmol) and cyclopropylacetylene (1.2 mmol) in water/tetrahydrofuran (2 ml:2 ml) was stirred for 3 h at room temperature. The mixture was filtered and evaporated. and the residue extracted with EtOAc (50 ml). The organic layer was washed brine, dried over Na₂SO₄ for 6 h, filtered, and the solvent evaporated in vacuo. Purification of the residue by column chromatography gave the title compound as white solid.

Colourless prisms were grown by slow evaporation from acetone solution at room temperature for two weeks. mp:389–391k; R_f = 0.30 (petroleum ether/EtOAc, 1:1); ¹H NMR (400 MHz, DMSO-d₆)σ: 7.69(1H, s), 5.86(1H, d, J = 3.6 Hz), 5.27(1H, d, J = 4.9 Hz), 5.19(1H, d, J = 6.4 Hz), 4.47(1H, dt, J = 10.2, 5.1 Hz), 4.42(1H, d, J = 3.6 Hz), 4.23(1H, d, J = 14.0, 8.0 Hz), 4.08–3.93(2H, m), 3.75(1H, dd, J = 8.8, 2.5 Hz), 1.92(1H, dq, J = 8.4, 5.0 Hz), 1.37(3H, s), 1.24(3H, s), 0.94–0.82(2H, m), 0.79–0.63(2H, m); ¹³C NMR (100 MHz, DMSO-d₆) σ: 153.61, 126.82, 115.95, 109.77, 89.90, 86.23, 78.05, 71.49, 58.80, 31.88, 31.39, 12.70, 11.72.

Computing details top

Data collection: FRAMBO (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids.
	Fig. 2. Packing diagram for (I).

4-Cyclopropyl-1-(6'-Deoxy-1',2'-O-isopropylidene-α-D-glucofuranosyl)-1H-1,2,3-triazole top

Crystal data top

C₁₄H₂₁N₃O₅	D_x = 1.331 Mg m⁻³
M_r = 311.34	Melting point = 389–391 K
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54178 Å
a = 8.5905 (3) Å	Cell parameters from 2697 reflections
b = 8.7215 (3) Å	θ = 4.3–67.0°
c = 20.7373 (7) Å	µ = 0.85 mm⁻¹
V = 1553.68 (9) Å³	T = 291 K
Z = 4	PRISMATIC, colourless
F(000) = 664	0.22 × 0.2 × 0.18 mm

Data collection top

Bruker MWPC diffractometer	2778 independent reflections
Radiation source: fine-focus sealed tube	2503 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 0 pixels mm^-1	θ_max = 67.1°, θ_min = 4.3°
phi and ω scans	h = −10→6
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −6→10
T_min = 0.835, T_max = 0.862	l = −24→22
5692 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.0567P)² + 0.1063P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2778 reflections	Δρ_max = 0.25 e Å⁻³
220 parameters	Δρ_min = −0.20 e Å⁻³
2 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0020 (3)

Crystal data top

C₁₄H₂₁N₃O₅	V = 1553.68 (9) Å³
M_r = 311.34	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 8.5905 (3) Å	µ = 0.85 mm⁻¹
b = 8.7215 (3) Å	T = 291 K
c = 20.7373 (7) Å	0.22 × 0.2 × 0.18 mm

Data collection top

Bruker MWPC diffractometer	2778 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2503 reflections with I > 2σ(I)
T_min = 0.835, T_max = 0.862	R_int = 0.028
5692 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	2 restraints
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.25 e Å⁻³
2778 reflections	Δρ_min = −0.20 e Å⁻³
220 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.0805 (2)	0.9329 (2)	0.39252 (9)	0.0556 (5)
O2	0.0625 (2)	1.0684 (2)	0.31968 (8)	0.0541 (5)
O3	0.2108 (2)	1.32136 (18)	0.44356 (9)	0.0487 (4)
O4	0.12445 (19)	0.99779 (18)	0.46166 (8)	0.0470 (4)
O5	0.5249 (2)	1.1144 (2)	0.44763 (9)	0.0517 (4)
N1	0.4448 (2)	0.7779 (2)	0.46218 (9)	0.0395 (4)
N2	0.3396 (2)	0.6662 (2)	0.45796 (11)	0.0461 (5)
N3	0.3860 (3)	0.5760 (2)	0.41084 (11)	0.0536 (5)
C1	−0.0064 (3)	1.0493 (3)	0.42728 (12)	0.0427 (5)
H1	−0.0800	1.1009	0.4561	0.051*
C2	0.0544 (3)	1.1602 (3)	0.37614 (12)	0.0458 (5)
H2	−0.0119	1.2508	0.3708	0.055*
C3	0.2187 (3)	1.1997 (3)	0.39848 (11)	0.0398 (5)
H3A	0.2871	1.2245	0.3621	0.048*
C4	0.2639 (2)	1.0486 (2)	0.43038 (11)	0.0378 (5)
H4	0.2922	0.9745	0.3968	0.045*
C5	0.3927 (2)	1.0555 (2)	0.47975 (11)	0.0401 (5)
H5A	0.3625	1.1273	0.5139	0.048*
C6	0.4246 (3)	0.8990 (3)	0.51006 (11)	0.0427 (5)
H6A	0.5179	0.9056	0.5363	0.051*
H6B	0.3387	0.8723	0.5382	0.051*
C7	0.5573 (3)	0.7605 (3)	0.41813 (13)	0.0486 (6)
H7	0.6429	0.8238	0.4115	0.058*
C8	0.5199 (4)	0.6308 (3)	0.38513 (14)	0.0560 (7)
C9	0.6279 (7)	0.5539 (8)	0.3376 (4)	0.0575 (13)	0.576 (5)
H9	0.7207	0.6118	0.3247	0.069*	0.576 (5)
C10	0.5544 (9)	0.4602 (11)	0.2880 (4)	0.0937 (19)	0.576 (5)
H10A	0.4419	0.4512	0.2890	0.112*	0.576 (5)
H10B	0.5990	0.4632	0.2450	0.112*	0.576 (5)
C11	0.6422 (10)	0.3805 (10)	0.3380 (4)	0.076 (2)	0.576 (5)
H11A	0.7418	0.3361	0.3262	0.091*	0.576 (5)
H11B	0.5842	0.3241	0.3703	0.091*	0.576 (5)
C12	−0.0353 (3)	0.9372 (3)	0.32677 (12)	0.0537 (6)
C13	0.0573 (5)	0.7939 (4)	0.31160 (18)	0.0822 (10)
H13A	0.1480	0.7901	0.3386	0.123*
H13B	0.0886	0.7957	0.2672	0.123*
H13C	−0.0060	0.7051	0.3194	0.123*
C14	−0.1795 (4)	0.9543 (5)	0.28580 (19)	0.0976 (14)
H14A	−0.2461	0.8672	0.2922	0.146*
H14B	−0.1503	0.9606	0.2412	0.146*
H14C	−0.2338	1.0460	0.2980	0.146*
C9A	0.5637 (10)	0.5566 (12)	0.3225 (5)	0.0575 (13)	0.424 (5)
H9A	0.5328	0.6124	0.2835	0.069*	0.424 (5)
C10A	0.7242 (11)	0.4953 (13)	0.3224 (5)	0.0937 (19)	0.424 (5)
H10C	0.7798	0.4917	0.3631	0.112*	0.424 (5)
H10D	0.7883	0.5136	0.2847	0.112*	0.424 (5)
C11A	0.5835 (14)	0.3960 (15)	0.3149 (7)	0.076 (2)	0.424 (5)
H11C	0.5634	0.3524	0.2727	0.091*	0.424 (5)
H11D	0.5550	0.3307	0.3509	0.091*	0.424 (5)
H5	0.591 (3)	1.141 (4)	0.4739 (12)	0.059 (9)*
H3	0.266 (3)	1.393 (3)	0.4302 (14)	0.058 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0553 (10)	0.0571 (10)	0.0543 (9)	−0.0242 (9)	0.0018 (8)	0.0009 (8)
O2	0.0620 (11)	0.0563 (10)	0.0439 (8)	−0.0223 (9)	−0.0041 (8)	0.0044 (8)
O3	0.0526 (9)	0.0281 (7)	0.0655 (11)	−0.0076 (7)	0.0121 (8)	−0.0079 (7)
O4	0.0394 (8)	0.0445 (8)	0.0573 (9)	−0.0097 (7)	−0.0010 (7)	0.0133 (7)
O5	0.0420 (9)	0.0476 (9)	0.0654 (11)	−0.0149 (7)	−0.0044 (8)	0.0029 (8)
N1	0.0358 (9)	0.0308 (8)	0.0521 (10)	−0.0021 (7)	−0.0022 (8)	0.0047 (8)
N2	0.0431 (10)	0.0332 (9)	0.0621 (11)	−0.0064 (8)	0.0011 (9)	0.0018 (9)
N3	0.0657 (13)	0.0322 (9)	0.0628 (12)	−0.0073 (10)	0.0019 (10)	−0.0037 (9)
C1	0.0357 (10)	0.0382 (11)	0.0542 (12)	−0.0002 (9)	0.0036 (10)	−0.0022 (10)
C2	0.0435 (12)	0.0362 (11)	0.0579 (14)	0.0003 (10)	−0.0021 (10)	0.0052 (10)
C3	0.0414 (11)	0.0291 (10)	0.0488 (12)	−0.0028 (9)	0.0066 (10)	−0.0005 (9)
C4	0.0369 (10)	0.0283 (10)	0.0483 (11)	−0.0003 (8)	0.0021 (9)	−0.0038 (9)
C5	0.0384 (11)	0.0320 (10)	0.0498 (11)	−0.0040 (9)	−0.0006 (9)	−0.0061 (9)
C6	0.0415 (12)	0.0397 (11)	0.0470 (11)	−0.0034 (9)	−0.0059 (9)	0.0011 (10)
C7	0.0426 (12)	0.0357 (11)	0.0676 (15)	−0.0003 (10)	0.0094 (11)	0.0072 (10)
C8	0.0673 (17)	0.0349 (11)	0.0658 (15)	0.0006 (11)	0.0148 (13)	0.0022 (11)
C9	0.049 (4)	0.0495 (16)	0.074 (4)	0.001 (3)	0.006 (3)	−0.003 (2)
C10	0.074 (3)	0.127 (5)	0.080 (3)	0.012 (4)	0.000 (3)	−0.046 (4)
C11	0.089 (6)	0.047 (2)	0.091 (6)	0.017 (4)	0.022 (4)	−0.001 (4)
C12	0.0585 (15)	0.0525 (14)	0.0502 (12)	−0.0192 (12)	−0.0062 (12)	0.0014 (12)
C13	0.091 (2)	0.0624 (19)	0.093 (2)	−0.0184 (18)	0.019 (2)	−0.0190 (18)
C14	0.092 (3)	0.107 (3)	0.093 (2)	−0.047 (2)	−0.042 (2)	0.038 (2)
C9A	0.049 (4)	0.0495 (16)	0.074 (4)	0.001 (3)	0.006 (3)	−0.003 (2)
C10A	0.074 (3)	0.127 (5)	0.080 (3)	0.012 (4)	0.000 (3)	−0.046 (4)
C11A	0.089 (6)	0.047 (2)	0.091 (6)	0.017 (4)	0.022 (4)	−0.001 (4)

Geometric parameters (Å, º) top

O1—C1	1.399 (3)	C7—C8	1.361 (4)
O1—C12	1.418 (3)	C8—C9	1.511 (8)
O2—C2	1.420 (3)	C8—C9A	1.499 (12)
O2—C12	1.428 (3)	C9—H9	0.9800
O3—C3	1.416 (3)	C9—C10	1.459 (10)
O3—H3	0.829 (18)	C9—C11	1.517 (11)
O4—C1	1.405 (3)	C10—H10A	0.9700
O4—C4	1.432 (3)	C10—H10B	0.9700
O5—C5	1.413 (3)	C10—C11	1.458 (11)
O5—H5	0.821 (18)	C11—H11A	0.9700
N1—N2	1.332 (3)	C11—H11B	0.9700
N1—C6	1.460 (3)	C12—C13	1.514 (4)
N1—C7	1.338 (3)	C12—C14	1.509 (4)
N2—N3	1.316 (3)	C13—H13A	0.9600
N3—C8	1.355 (4)	C13—H13B	0.9600
C1—H1	0.9800	C13—H13C	0.9600
C1—C2	1.527 (3)	C14—H14A	0.9600
C2—H2	0.9800	C14—H14B	0.9600
C2—C3	1.525 (3)	C14—H14C	0.9600
C3—H3A	0.9800	C9A—H9A	0.9800
C3—C4	1.525 (3)	C9A—C10A	1.479 (12)
C4—H4	0.9800	C9A—C11A	1.420 (17)
C4—C5	1.509 (3)	C10A—H10C	0.9700
C5—H5A	0.9800	C10A—H10D	0.9700
C5—C6	1.528 (3)	C10A—C11A	1.495 (18)
C6—H6A	0.9700	C11A—H11C	0.9700
C6—H6B	0.9700	C11A—H11D	0.9700
C7—H7	0.9300

C1—O1—C12	110.60 (18)	C8—C9—H9	116.7
C2—O2—C12	109.78 (18)	C8—C9—C11	119.2 (6)
C3—O3—H3	108 (2)	C10—C9—C8	116.3 (5)
C1—O4—C4	109.89 (16)	C10—C9—H9	116.7
C5—O5—H5	110 (2)	C10—C9—C11	58.6 (5)
N2—N1—C6	119.59 (19)	C11—C9—H9	116.7
N2—N1—C7	111.23 (19)	C9—C10—H10A	117.5
C7—N1—C6	129.17 (19)	C9—C10—H10B	117.5
N3—N2—N1	106.30 (19)	H10A—C10—H10B	114.6
N2—N3—C8	109.8 (2)	C11—C10—C9	62.7 (5)
O1—C1—O4	113.18 (19)	C11—C10—H10A	117.5
O1—C1—H1	110.7	C11—C10—H10B	117.5
O1—C1—C2	104.92 (19)	C9—C11—H11A	117.9
O4—C1—H1	110.7	C9—C11—H11B	117.9
O4—C1—C2	106.35 (17)	C10—C11—C9	58.7 (5)
C2—C1—H1	110.7	C10—C11—H11A	117.9
O2—C2—C1	103.44 (18)	C10—C11—H11B	117.9
O2—C2—H2	112.9	H11A—C11—H11B	115.1
O2—C2—C3	109.4 (2)	O1—C12—O2	106.32 (19)
C1—C2—H2	112.9	O1—C12—C13	108.8 (3)
C3—C2—C1	104.40 (18)	O1—C12—C14	108.6 (3)
C3—C2—H2	112.9	O2—C12—C13	109.3 (2)
O3—C3—C2	109.04 (18)	O2—C12—C14	110.2 (3)
O3—C3—H3A	111.8	C14—C12—C13	113.3 (3)
O3—C3—C4	111.92 (19)	C12—C13—H13A	109.5
C2—C3—H3A	111.8	C12—C13—H13B	109.5
C2—C3—C4	99.90 (17)	C12—C13—H13C	109.5
C4—C3—H3A	111.8	H13A—C13—H13B	109.5
O4—C4—C3	104.53 (17)	H13A—C13—H13C	109.5
O4—C4—H4	109.0	H13B—C13—H13C	109.5
O4—C4—C5	108.58 (18)	C12—C14—H14A	109.5
C3—C4—H4	109.0	C12—C14—H14B	109.5
C5—C4—C3	116.50 (18)	C12—C14—H14C	109.5
C5—C4—H4	109.0	H14A—C14—H14B	109.5
O5—C5—C4	106.52 (18)	H14A—C14—H14C	109.5
O5—C5—H5A	108.7	H14B—C14—H14C	109.5
O5—C5—C6	111.98 (18)	C8—C9A—H9A	115.6
C4—C5—H5A	108.7	C10A—C9A—C8	113.0 (7)
C4—C5—C6	112.02 (17)	C10A—C9A—H9A	115.6
C6—C5—H5A	108.7	C11A—C9A—C8	123.5 (10)
N1—C6—C5	112.82 (18)	C11A—C9A—H9A	115.6
N1—C6—H6A	109.0	C11A—C9A—C10A	62.1 (8)
N1—C6—H6B	109.0	C9A—C10A—H10C	118.1
C5—C6—H6A	109.0	C9A—C10A—H10D	118.1
C5—C6—H6B	109.0	C9A—C10A—C11A	57.0 (7)
H6A—C6—H6B	107.8	H10C—C10A—H10D	115.3
N1—C7—H7	127.3	C11A—C10A—H10C	118.1
N1—C7—C8	105.5 (2)	C11A—C10A—H10D	118.1
C8—C7—H7	127.3	C9A—C11A—C10A	60.9 (7)
N3—C8—C7	107.2 (2)	C9A—C11A—H11C	117.7
N3—C8—C9	128.4 (3)	C9A—C11A—H11D	117.7
N3—C8—C9A	113.7 (4)	C10A—C11A—H11C	117.7
C7—C8—C9	123.5 (4)	C10A—C11A—H11D	117.7
C7—C8—C9A	137.3 (4)	H11C—C11A—H11D	114.8
C9A—C8—C9	24.4 (3)

O1—C1—C2—O2	−21.9 (2)	C2—O2—C12—O1	−11.0 (3)
O1—C1—C2—C3	−136.45 (19)	C2—O2—C12—C13	−128.3 (3)
O2—C2—C3—O3	164.93 (18)	C2—O2—C12—C14	106.5 (3)
O2—C2—C3—C4	−77.6 (2)	C2—C3—C4—O4	−38.2 (2)
O3—C3—C4—O4	77.1 (2)	C2—C3—C4—C5	−158.00 (19)
O3—C3—C4—C5	−42.7 (3)	C3—C4—C5—O5	−59.1 (2)
O4—C1—C2—O2	98.2 (2)	C3—C4—C5—C6	178.16 (19)
O4—C1—C2—C3	−16.3 (2)	C4—O4—C1—O1	106.0 (2)
O4—C4—C5—O5	−176.68 (17)	C4—O4—C1—C2	−8.7 (2)
O4—C4—C5—C6	60.6 (2)	C4—C5—C6—N1	50.0 (2)
O5—C5—C6—N1	−69.6 (2)	C6—N1—N2—N3	179.2 (2)
N1—N2—N3—C8	−0.2 (3)	C6—N1—C7—C8	−179.0 (2)
N1—C7—C8—N3	0.1 (3)	C7—N1—N2—N3	0.3 (3)
N1—C7—C8—C9	−170.2 (4)	C7—N1—C6—C5	65.6 (3)
N1—C7—C8—C9A	163.2 (6)	C7—C8—C9—C10	−155.2 (6)
N2—N1—C6—C5	−113.0 (2)	C7—C8—C9—C11	137.6 (6)
N2—N1—C7—C8	−0.2 (3)	C7—C8—C9A—C10A	70.7 (11)
N2—N3—C8—C7	0.1 (3)	C7—C8—C9A—C11A	141.4 (9)
N2—N3—C8—C9	169.7 (4)	C8—C9—C10—C11	−109.7 (7)
N2—N3—C8—C9A	−167.5 (5)	C8—C9—C11—C10	104.7 (7)
N3—C8—C9—C10	36.6 (9)	C8—C9A—C10A—C11A	116.9 (11)
N3—C8—C9—C11	−30.5 (8)	C8—C9A—C11A—C10A	−100.3 (9)
N3—C8—C9A—C10A	−127.0 (8)	C9—C8—C9A—C10A	5.6 (10)
N3—C8—C9A—C11A	−56.2 (10)	C9—C8—C9A—C11A	76.4 (16)
C1—O1—C12—O2	−4.1 (3)	C12—O1—C1—O4	−99.3 (2)
C1—O1—C12—C13	113.5 (2)	C12—O1—C1—C2	16.3 (3)
C1—O1—C12—C14	−122.7 (3)	C12—O2—C2—C1	20.2 (3)
C1—O4—C4—C3	30.3 (2)	C12—O2—C2—C3	131.0 (2)
C1—O4—C4—C5	155.31 (18)	C9A—C8—C9—C10	−22.7 (12)
C1—C2—C3—O3	−84.9 (2)	C9A—C8—C9—C11	−89.8 (16)
C1—C2—C3—C4	32.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N3ⁱ	0.83 (2)	1.95 (2)	2.767 (3)	171 (3)
O5—H5···O3ⁱⁱ	0.82 (3)	2.02 (3)	2.821 (3)	164 (3)
C7—H7···O1ⁱⁱⁱ	0.93	2.59	3.496 (3)	165

Symmetry codes: (i) x, y+1, z; (ii) x+1/2, −y+5/2, −z+1; (iii) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N3ⁱ	0.829 (18)	1.945 (19)	2.767 (3)	171 (3)
O5—H5···O3ⁱⁱ	0.82 (3)	2.02 (3)	2.821 (3)	164 (3)
C7—H7···O1ⁱⁱⁱ	0.93	2.59	3.496 (3)	165

Symmetry codes: (i) x, y+1, z; (ii) x+1/2, −y+5/2, −z+1; (iii) x+1, y, z.

Acknowledgements

We gratefully acknowledge the financial support of the National Natural Science Foundation of China (grant No. 81172937).

References

Alvarez, R., Velazquez, S., San-Felix, A., Aquaro, S. & De Clercq, E. (1994). J. Med. Chem. 37, 4185–4194. CrossRef CAS PubMed Web of Science Google Scholar
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Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 69| Part 9| September 2013| Page o1386

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-Cyclo­propyl-1-(6′-de­­oxy-1′,2′-O-iso­propyl­­idene-α-D-gluco­furanos­yl)-1H-1,2,3-triazole

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organic compounds

4-Cyclopropyl-1-(6′-deoxy-1′,2′-O-isopropylidene-α-D-glucofuranosyl)-1H-1,2,3-triazole