Benzotriazol-1-yl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enpyranoside

In the title compound {systematic name: [3(S)-acetyloxy-6(S)-(1H-1,2,3-benzotriazol-1-yl)-3,6-dihydro-2H-pyran-2(S)-yl]methyl acetate}, C₁₆H₁₇N₃O₅, weak C—H...O hydrogen bonds link the mol­ecules to form a three-dimensional network consisting of linked helical chains.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.046
• wR factor = 0.094
• Data-to-parameter ratio = 8.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.48
         From the CIF: _reflns_number_total               1883
         Count of symmetry unique reflns         1903
         Completeness (_total/calc)             98.95%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.

---

Computing details

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

6(R)-Acetoxymethyl-5(S)-acetyl-2(S)-(benzotriazol-1-yl)-5,6-dihydro-2H-pyran

Crystal data

C16H17N3O5	Dx = 1.371 Mg m^−3
Mr = 331.33	Melting point: 382 K
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 5.5167 (3) Å	Cell parameters from 1883 reflections
b = 17.7388 (11) Å	θ = 3.4–27.5°
c = 8.2217 (5) Å	µ = 0.10 mm^−1
β = 94.139 (3)°	T = 120 K
V = 802.47 (8) Å^3	Plate, colourless
Z = 2	0.26 × 0.24 × 0.04 mm
F(000) = 348

Data collection

Nonius KappaCCD diffractometer	1883 independent reflections
Radiation source: fine-focus sealed X-ray tube	1341 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.071
φ scans and ω scans with κ offsets	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −7→7
Tmin = 0.974, Tmax = 0.996	k = −19→23
6197 measured reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0424P)^2] where P = (Fo^2 + 2Fc^2)/3
1883 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.19 e Å^−3
1 restraint	Δρmin = −0.21 e Å^−3

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.7679 (4)	0.69893 (15)	0.6608 (3)	0.0254 (6)
C11	0.6080 (5)	0.7425 (2)	0.7612 (3)	0.0250 (7)
C12	0.5295 (5)	0.8153 (2)	0.6835 (4)	0.0284 (7)
C13	0.5810 (6)	0.8808 (2)	0.7532 (4)	0.0298 (8)
C14	0.7404 (5)	0.88614 (19)	0.9090 (4)	0.0244 (7)
O14	0.9202 (4)	0.94485 (12)	0.8918 (3)	0.0272 (5)
C141	0.8755 (6)	1.01337 (19)	0.9523 (4)	0.0261 (8)
O141	0.6920 (4)	1.02814 (15)	1.0167 (3)	0.0459 (7)
C142	1.0753 (6)	1.0668 (2)	0.9242 (4)	0.0318 (8)
C15	0.8839 (5)	0.81421 (18)	0.9377 (3)	0.0227 (7)
C151	1.0075 (5)	0.8129 (2)	1.1064 (4)	0.0267 (7)
O15	1.1599 (4)	0.74645 (12)	1.1233 (2)	0.0291 (5)
C152	1.3724 (5)	0.7541 (2)	1.2157 (4)	0.0263 (7)
O151	1.4415 (4)	0.81303 (13)	1.2726 (3)	0.0324 (6)
C153	1.5006 (6)	0.68044 (19)	1.2367 (4)	0.0286 (8)
O16	0.7184 (4)	0.75127 (12)	0.9219 (2)	0.0243 (5)
N2	0.9585 (4)	0.73299 (17)	0.5913 (3)	0.0318 (7)
N3	1.0889 (5)	0.68069 (17)	0.5264 (3)	0.0343 (7)
C3A	0.9857 (6)	0.6115 (2)	0.5538 (3)	0.0276 (8)
C4	1.0527 (6)	0.5388 (2)	0.5080 (4)	0.0339 (9)
C5	0.9114 (7)	0.4802 (2)	0.5518 (5)	0.0396 (9)
C6	0.7022 (7)	0.4923 (2)	0.6395 (4)	0.0379 (9)
C7	0.6326 (6)	0.5629 (2)	0.6851 (4)	0.0317 (8)
C7A	0.7781 (5)	0.62277 (19)	0.6408 (4)	0.0260 (8)
H11	0.4578	0.7116	0.7706	0.030*
H12	0.4397	0.8145	0.5805	0.034*
H13	0.5161	0.9256	0.7041	0.036*
H14	0.6410	0.8971	1.0032	0.029*
H14A	1.0485	1.1142	0.9816	0.048*
H14B	1.0784	1.0767	0.8071	0.048*
H14C	1.2307	1.0448	0.9654	0.048*
H15	1.0080	0.8097	0.8553	0.027*
H15A	1.1077	0.8588	1.1250	0.032*
H15B	0.8844	0.8118	1.1883	0.032*
H15C	1.4447	0.6543	1.3321	0.043*
H15D	1.6762	0.6892	1.2525	0.043*
H15E	1.4654	0.6494	1.1392	0.043*
H4	1.1917	0.5307	0.4486	0.041*
H5	0.9537	0.4302	0.5231	0.048*
H6	0.6075	0.4502	0.6675	0.046*
H7	0.4926	0.5707	0.7438	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0253 (14)	0.0284 (18)	0.0227 (13)	−0.0050 (12)	0.0022 (12)	−0.0018 (11)
C11	0.0186 (13)	0.032 (2)	0.0240 (15)	−0.0050 (15)	−0.0005 (13)	−0.0060 (15)
C12	0.0235 (15)	0.034 (2)	0.0272 (16)	0.0003 (16)	−0.0031 (13)	0.0016 (17)
C13	0.0229 (15)	0.030 (2)	0.036 (2)	0.0049 (16)	0.0003 (16)	0.0080 (17)
C14	0.0195 (15)	0.0246 (19)	0.0289 (17)	−0.0020 (15)	−0.0007 (14)	0.0024 (14)
O14	0.0245 (11)	0.0228 (13)	0.0349 (12)	−0.0037 (10)	0.0066 (10)	−0.0027 (10)
C141	0.0298 (17)	0.028 (2)	0.0201 (15)	−0.0007 (15)	0.0001 (15)	0.0032 (14)
O141	0.0421 (14)	0.0344 (15)	0.0640 (17)	−0.0003 (13)	0.0232 (14)	−0.0055 (14)
C142	0.0343 (18)	0.029 (2)	0.0313 (17)	−0.0085 (16)	−0.0031 (15)	0.0019 (15)
C15	0.0208 (14)	0.0198 (19)	0.0276 (15)	−0.0023 (15)	0.0021 (13)	−0.0036 (15)
C151	0.0270 (15)	0.025 (2)	0.0274 (16)	0.0036 (15)	−0.0047 (13)	−0.0049 (15)
O15	0.0264 (11)	0.0267 (14)	0.0330 (12)	0.0010 (11)	−0.0068 (10)	−0.0051 (11)
C152	0.0252 (15)	0.031 (2)	0.0225 (15)	0.0015 (16)	0.0018 (13)	0.0024 (16)
O151	0.0299 (12)	0.0295 (15)	0.0362 (12)	0.0013 (12)	−0.0094 (10)	−0.0091 (12)
C153	0.0294 (17)	0.031 (2)	0.0254 (16)	0.0038 (15)	0.0008 (14)	0.0023 (15)
O16	0.0241 (10)	0.0270 (13)	0.0215 (10)	−0.0052 (10)	−0.0015 (9)	−0.0001 (10)
N2	0.0254 (14)	0.0425 (19)	0.0282 (14)	−0.0123 (14)	0.0057 (12)	−0.0048 (14)
N3	0.0297 (14)	0.043 (2)	0.0307 (15)	−0.0037 (14)	0.0066 (13)	−0.0072 (14)
C3A	0.0273 (16)	0.034 (2)	0.0209 (15)	0.0012 (16)	−0.0003 (14)	−0.0049 (15)
C4	0.0308 (18)	0.041 (3)	0.0284 (17)	0.0076 (17)	−0.0065 (15)	−0.0063 (16)
C5	0.047 (2)	0.031 (2)	0.039 (2)	0.0090 (19)	−0.0118 (18)	−0.0034 (17)
C6	0.042 (2)	0.035 (2)	0.036 (2)	−0.0055 (18)	−0.0069 (18)	0.0067 (17)
C7	0.0312 (18)	0.037 (2)	0.0263 (17)	−0.0021 (17)	−0.0014 (15)	0.0025 (16)
C7A	0.0257 (16)	0.032 (2)	0.0194 (15)	−0.0007 (15)	−0.0045 (13)	−0.0009 (13)

Geometric parameters (Å, º)

N1—C7A	1.363 (4)	C151—O15	1.449 (4)
N1—N2	1.373 (3)	C151—H15A	0.99
N1—C11	1.470 (4)	C151—H15B	0.99
C11—O16	1.423 (3)	O15—C152	1.357 (4)
C11—C12	1.492 (5)	C152—O151	1.197 (4)
C11—H11	1.00	C152—C153	1.489 (5)
C12—C13	1.318 (5)	C153—H15C	0.98
C12—H12	0.95	C153—H15D	0.98
C13—C14	1.503 (5)	C153—H15E	0.98
C13—H13	0.95	N2—N3	1.311 (4)
C14—O14	1.452 (4)	N3—C3A	1.379 (4)
C14—C15	1.511 (4)	C3A—C4	1.399 (5)
C14—H14	1.00	C3A—C7A	1.408 (4)
O14—C141	1.343 (4)	C4—C5	1.364 (5)
C141—O141	1.205 (4)	C4—H4	0.95
C141—C142	1.485 (5)	C5—C6	1.421 (5)
C142—H14A	0.98	C5—H5	0.95
C142—H14B	0.98	C6—C7	1.370 (5)
C142—H14C	0.98	C6—H6	0.95
C15—O16	1.442 (4)	C7—C7A	1.395 (5)
C15—C151	1.501 (4)	C7—H7	0.95
C15—H15	1.00
C7A—N1—N2	110.3 (2)	O15—C151—C15	108.8 (2)
C7A—N1—C11	128.3 (2)	O15—C151—H15A	109.9
N2—N1—C11	120.8 (3)	C15—C151—H15A	109.9
O16—C11—N1	110.2 (2)	O15—C151—H15B	109.9
O16—C11—C12	113.2 (3)	C15—C151—H15B	109.9
N1—C11—C12	112.4 (2)	H15A—C151—H15B	108.3
O16—C11—H11	106.9	C152—O15—C151	116.4 (2)
N1—C11—H11	106.9	O151—C152—O15	122.9 (3)
C12—C11—H11	106.9	O151—C152—C153	125.9 (3)
C13—C12—C11	122.1 (3)	O15—C152—C153	111.2 (3)
C13—C12—H12	119.0	C152—C153—H15C	109.5
C11—C12—H12	119.0	C152—C153—H15D	109.5
C12—C13—C14	121.4 (3)	H15C—C153—H15D	109.5
C12—C13—H13	119.3	C152—C153—H15E	109.5
C14—C13—H13	119.3	H15C—C153—H15E	109.5
O14—C14—C13	108.9 (3)	H15D—C153—H15E	109.5
O14—C14—C15	105.5 (2)	C11—O16—C15	113.2 (2)
C13—C14—C15	110.4 (3)	N3—N2—N1	108.5 (3)
O14—C14—H14	110.7	N2—N3—C3A	108.6 (3)
C13—C14—H14	110.7	N3—C3A—C4	131.0 (3)
C15—C14—H14	110.7	N3—C3A—C7A	108.5 (3)
C141—O14—C14	117.9 (2)	C4—C3A—C7A	120.5 (3)
O141—C141—O14	122.8 (3)	C5—C4—C3A	117.7 (3)
O141—C141—C142	125.9 (3)	C5—C4—H4	121.2
O14—C141—C142	111.2 (3)	C3A—C4—H4	121.2
C141—C142—H14A	109.5	C4—C5—C6	121.3 (4)
C141—C142—H14B	109.5	C4—C5—H5	119.4
H14A—C142—H14B	109.5	C6—C5—H5	119.4
C141—C142—H14C	109.5	C7—C6—C5	122.1 (3)
H14A—C142—H14C	109.5	C7—C6—H6	118.9
H14B—C142—H14C	109.5	C5—C6—H6	118.9
O16—C15—C151	108.3 (2)	C6—C7—C7A	116.5 (3)
O16—C15—C14	108.6 (2)	C6—C7—H7	121.8
C151—C15—C14	110.8 (3)	C7A—C7—H7	121.8
O16—C15—H15	109.7	N1—C7A—C7	133.9 (3)
C151—C15—H15	109.7	N1—C7A—C3A	104.2 (3)
C14—C15—H15	109.7	C7—C7A—C3A	121.9 (3)
C7A—N1—C11—O16	89.1 (3)	C12—C11—O16—C15	−42.2 (3)
N2—N1—C11—O16	−80.9 (3)	C151—C15—O16—C11	−174.2 (2)
C7A—N1—C11—C12	−143.6 (3)	C14—C15—O16—C11	65.4 (3)
N2—N1—C11—C12	46.4 (4)	C7A—N1—N2—N3	0.5 (3)
O16—C11—C12—C13	6.2 (4)	C11—N1—N2—N3	172.1 (2)
N1—C11—C12—C13	−119.5 (3)	N1—N2—N3—C3A	−0.4 (3)
C11—C12—C13—C14	5.3 (4)	N2—N3—C3A—C4	179.1 (3)
C12—C13—C14—O14	132.8 (3)	N2—N3—C3A—C7A	0.2 (3)
C12—C13—C14—C15	17.5 (4)	N3—C3A—C4—C5	−179.3 (3)
C13—C14—O14—C141	97.5 (3)	C7A—C3A—C4—C5	−0.5 (5)
C15—C14—O14—C141	−144.1 (3)	C3A—C4—C5—C6	0.6 (5)
C14—O14—C141—O141	−1.4 (4)	C4—C5—C6—C7	−0.3 (5)
C14—O14—C141—C142	−179.7 (2)	C5—C6—C7—C7A	0.0 (5)
O14—C14—C15—O16	−168.1 (2)	N2—N1—C7A—C7	−179.4 (3)
C13—C14—C15—O16	−50.7 (3)	C11—N1—C7A—C7	9.9 (5)
O14—C14—C15—C151	73.1 (3)	N2—N1—C7A—C3A	−0.4 (3)
C13—C14—C15—C151	−169.4 (3)	C11—N1—C7A—C3A	−171.1 (3)
O16—C15—C151—O15	66.2 (3)	C6—C7—C7A—N1	178.9 (3)
C14—C15—C151—O15	−174.9 (2)	C6—C7—C7A—C3A	0.0 (5)
C15—C151—O15—C152	144.3 (2)	N3—C3A—C7A—N1	0.1 (3)
C151—O15—C152—O151	−4.8 (4)	C4—C3A—C7A—N1	−178.9 (3)
C151—O15—C152—C153	174.5 (2)	N3—C3A—C7A—C7	179.2 (3)
N1—C11—O16—C15	84.6 (3)	C4—C3A—C7A—C7	0.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O141^i	0.95	2.40	3.198 (4)	141
C6—H6···O151^ii	0.95	2.50	3.369 (5)	152
C12—H12···O151^iii	0.95	2.53	3.378 (4)	148
C14—H14···O141	1.00	2.34	2.690 (4)	99
C151—H15A···O151	0.99	2.28	2.670 (4)	102

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