2,3,4,6-Tetra-O-acetyl-β-D-gluco­pyran­osyl azide

The structure of the title compound, C₁₄H₁₉N₃O₉, has been determined at 100 K. The six-membered ring exhibits a chair conformation, and all non-H substituents are found in equatorial positions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.103
• Data-to-parameter ratio = 10.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N1     -   N2      ..       7.56 su

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.803     0.960
            Tmin' and Tmax expected:      0.963     0.964
            RR' =      0.837
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.84
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.49
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.68 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.63 Ratio

Alert level G
REFLT03_ALERT_4_G 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.
           From the CIF: _diffrn_reflns_theta_max           30.48
           From the CIF: _reflns_number_total               2935
           Count of symmetry unique reflns         2943
           Completeness (_total/calc)             99.73%
           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

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1997-2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl azide

Crystal data

C14H19N3O9	F(000) = 784
Mr = 373.32	Dx = 1.457 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 17967 reflections
a = 7.2970 (3) Å	θ = 2.6–30.5°
b = 14.7022 (7) Å	µ = 0.12 mm^−1
c = 15.8692 (7) Å	T = 100 K
V = 1702.48 (13) Å^3	Block, colourless
Z = 4	0.30 × 0.30 × 0.30 mm

Data collection

Bruker AXS SMART APEX CCD diffractometer	2935 independent reflections
Radiation source: fine-focus sealed tube	2914 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 30.5°, θmin = 1.9°
Absorption correction: multi scan (SADABS in SAINT-Plus; Bruker, 1997-1999)	h = −10→10
Tmin = 0.803, Tmax = 0.96	k = −20→20
21165 measured reflections	l = −22→22

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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F^2) = 0.103	Only H-atom coordinates refined
S = 1.20	w = 1/[σ^2(Fo^2) + (0.0539P)^2 + 0.3882P] where P = (Fo^2 + 2Fc^2)/3
2935 reflections	(Δ/σ)max = 0.001
292 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.65273 (17)	0.47618 (8)	0.90833 (7)	0.0122 (2)
O2	0.57229 (18)	0.68192 (8)	0.78618 (7)	0.0148 (2)
O3	0.4611 (3)	0.63612 (10)	0.66020 (9)	0.0287 (3)
O4	0.23497 (17)	0.65738 (8)	0.86977 (8)	0.0140 (2)
O5	0.2330 (2)	0.77203 (10)	0.96414 (9)	0.0233 (3)
O6	0.29033 (16)	0.57063 (8)	1.03714 (7)	0.0133 (2)
O7	0.0174 (2)	0.52221 (12)	0.98786 (9)	0.0255 (3)
O8	0.47658 (18)	0.36273 (8)	1.03117 (8)	0.0154 (2)
O9	0.5337 (3)	0.31062 (12)	1.16092 (10)	0.0320 (4)
N1	0.7798 (2)	0.51022 (11)	0.77776 (9)	0.0163 (3)
N2	0.9457 (2)	0.49310 (11)	0.78559 (10)	0.0182 (3)
N3	1.0938 (3)	0.47367 (14)	0.78272 (12)	0.0299 (4)
C1	0.6965 (2)	0.54914 (11)	0.85326 (10)	0.0126 (3)
C2	0.5212 (2)	0.59814 (10)	0.82645 (10)	0.0117 (3)
C3	0.4061 (2)	0.62418 (11)	0.90266 (10)	0.0118 (3)
C4	0.3800 (2)	0.54280 (11)	0.96094 (10)	0.0108 (3)
C5	0.5732 (2)	0.51091 (11)	0.98431 (10)	0.0112 (3)
C6	0.5847 (2)	0.44121 (11)	1.05314 (10)	0.0130 (3)
C7	0.5298 (3)	0.69370 (12)	0.70319 (11)	0.0177 (3)
C8	0.5782 (3)	0.78823 (13)	0.67646 (12)	0.0238 (4)
C9	0.1665 (2)	0.73464 (11)	0.90391 (10)	0.0148 (3)
C10	0.0002 (3)	0.76592 (13)	0.85745 (12)	0.0201 (3)
C11	0.1068 (2)	0.55505 (12)	1.04335 (11)	0.0156 (3)
C12	0.0394 (3)	0.58549 (13)	1.12744 (12)	0.0190 (3)
C13	0.4660 (3)	0.29960 (12)	1.09301 (11)	0.0185 (3)
C14	0.3678 (3)	0.21611 (14)	1.06349 (15)	0.0289 (4)
H1	0.778 (4)	0.588 (2)	0.8803 (19)	0.035*
H2	0.458 (4)	0.563 (2)	0.7904 (18)	0.035*
H3	0.464 (5)	0.671 (2)	0.9342 (18)	0.035*
H4	0.313 (4)	0.498 (2)	0.9369 (19)	0.035*
H5	0.639 (4)	0.567 (2)	1.0034 (18)	0.035*
H6A	0.716 (4)	0.424 (2)	1.0619 (19)	0.035*
H8A	0.574 (5)	0.788 (2)	0.616 (2)	0.043*
H10A	−0.102 (5)	0.757 (2)	0.897 (2)	0.043*
H12A	0.049 (5)	0.648 (2)	1.131 (2)	0.043*
H14A	0.345 (5)	0.183 (2)	1.108 (2)	0.043*
H6B	0.536 (4)	0.468 (2)	1.1034 (19)	0.035*
H8B	0.695 (5)	0.809 (2)	0.700 (2)	0.043*
H10B	−0.014 (5)	0.734 (2)	0.809 (2)	0.043*
H12B	0.110 (5)	0.563 (2)	1.173 (2)	0.043*
H14B	0.444 (5)	0.183 (2)	1.022 (2)	0.043*
H8C	0.487 (5)	0.828 (2)	0.698 (2)	0.043*
H10C	0.007 (5)	0.827 (2)	0.849 (2)	0.043*
H12C	−0.078 (5)	0.567 (2)	1.133 (2)	0.043*
H14C	0.255 (5)	0.232 (2)	1.036 (2)	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0151 (5)	0.0094 (5)	0.0122 (5)	0.0010 (4)	0.0010 (4)	0.0005 (4)
O2	0.0196 (6)	0.0127 (5)	0.0121 (5)	−0.0004 (4)	−0.0008 (5)	0.0030 (4)
O3	0.0475 (9)	0.0218 (6)	0.0169 (6)	−0.0032 (7)	−0.0082 (6)	0.0005 (5)
O4	0.0143 (5)	0.0129 (5)	0.0150 (5)	0.0045 (4)	−0.0020 (4)	−0.0015 (4)
O5	0.0256 (6)	0.0213 (6)	0.0231 (6)	0.0084 (6)	−0.0050 (6)	−0.0097 (5)
O6	0.0126 (5)	0.0158 (5)	0.0116 (5)	−0.0008 (4)	0.0011 (4)	−0.0023 (4)
O7	0.0150 (6)	0.0402 (8)	0.0212 (6)	−0.0040 (6)	−0.0017 (5)	−0.0069 (6)
O8	0.0188 (5)	0.0128 (5)	0.0145 (5)	−0.0038 (5)	−0.0027 (5)	0.0017 (4)
O9	0.0413 (9)	0.0323 (8)	0.0226 (7)	−0.0114 (7)	−0.0095 (7)	0.0137 (6)
N1	0.0145 (7)	0.0215 (7)	0.0129 (6)	0.0037 (6)	0.0017 (5)	−0.0015 (5)
N2	0.0204 (7)	0.0184 (7)	0.0158 (6)	0.0005 (6)	0.0017 (6)	−0.0025 (5)
N3	0.0196 (8)	0.0397 (10)	0.0303 (9)	0.0065 (7)	0.0011 (7)	−0.0147 (8)
C1	0.0137 (6)	0.0114 (6)	0.0126 (6)	0.0003 (5)	0.0008 (6)	−0.0004 (5)
C2	0.0145 (6)	0.0099 (6)	0.0107 (6)	0.0006 (5)	0.0004 (5)	0.0002 (5)
C3	0.0111 (6)	0.0115 (6)	0.0127 (6)	0.0016 (6)	0.0000 (5)	−0.0004 (5)
C4	0.0108 (6)	0.0113 (6)	0.0103 (6)	0.0001 (5)	0.0002 (5)	−0.0001 (5)
C5	0.0108 (6)	0.0116 (6)	0.0111 (6)	0.0002 (5)	−0.0013 (5)	−0.0001 (5)
C6	0.0162 (7)	0.0120 (6)	0.0108 (6)	−0.0017 (6)	−0.0028 (6)	−0.0001 (5)
C7	0.0239 (8)	0.0158 (7)	0.0133 (7)	0.0034 (7)	0.0004 (6)	0.0013 (5)
C8	0.0372 (10)	0.0181 (8)	0.0162 (7)	0.0002 (8)	−0.0010 (8)	0.0058 (6)
C9	0.0157 (7)	0.0142 (7)	0.0147 (7)	0.0030 (6)	0.0026 (6)	0.0004 (6)
C10	0.0203 (8)	0.0210 (8)	0.0191 (7)	0.0093 (7)	−0.0030 (7)	−0.0023 (6)
C11	0.0138 (7)	0.0168 (7)	0.0162 (7)	0.0010 (6)	0.0014 (6)	0.0014 (6)
C12	0.0182 (8)	0.0218 (8)	0.0171 (7)	−0.0001 (7)	0.0036 (6)	0.0004 (6)
C13	0.0182 (7)	0.0174 (7)	0.0198 (7)	−0.0019 (6)	0.0010 (6)	0.0064 (6)
C14	0.0329 (10)	0.0190 (8)	0.0348 (10)	−0.0109 (8)	−0.0027 (9)	0.0073 (8)

Geometric parameters (Å, º)

O1—C1	1.4201 (19)	C4—C5	1.531 (2)
O1—C5	1.4322 (19)	C4—H4	0.91 (3)
O2—C7	1.364 (2)	C5—C6	1.500 (2)
O2—C2	1.4370 (19)	C5—H5	1.00 (3)
O3—C7	1.197 (2)	C6—H6A	1.00 (3)
O4—C9	1.3540 (19)	C6—H6B	0.95 (3)
O4—C3	1.439 (2)	C7—C8	1.495 (3)
O5—C9	1.205 (2)	C8—H8A	0.95 (3)
O6—C11	1.362 (2)	C8—H8B	0.98 (4)
O6—C4	1.4345 (19)	C8—H8C	0.95 (4)
O7—C11	1.197 (2)	C9—C10	1.493 (2)
O8—C13	1.353 (2)	C10—H10A	0.98 (4)
O8—C6	1.441 (2)	C10—H10B	0.90 (3)
O9—C13	1.196 (2)	C10—H10C	0.91 (4)
N1—N2	1.243 (2)	C11—C12	1.491 (2)
N1—C1	1.460 (2)	C12—H12A	0.93 (4)
N2—N3	1.119 (3)	C12—H12B	0.95 (3)
C1—C2	1.529 (2)	C12—H12C	0.90 (4)
C1—H1	0.93 (3)	C13—C14	1.497 (3)
C2—C3	1.521 (2)	C14—H14A	0.87 (4)
C2—H2	0.90 (3)	C14—H14B	0.99 (4)
C3—C4	1.524 (2)	C14—H14C	0.95 (4)
C3—H3	0.95 (3)
C1—O1—C5	109.88 (12)	O8—C6—H6B	109.0 (19)
C7—O2—C2	118.63 (13)	C5—C6—H6B	108.1 (19)
C9—O4—C3	117.38 (13)	H6A—C6—H6B	110 (3)
C11—O6—C4	117.47 (13)	O3—C7—O2	123.76 (17)
C13—O8—C6	113.89 (13)	O3—C7—C8	126.46 (17)
N2—N1—C1	113.74 (14)	O2—C7—C8	109.77 (15)
N3—N2—N1	171.4 (2)	C7—C8—H8A	106 (2)
O1—C1—N1	107.61 (13)	C7—C8—H8B	113 (2)
O1—C1—C2	109.81 (13)	H8A—C8—H8B	115 (3)
N1—C1—C2	107.74 (13)	C7—C8—H8C	108 (2)
O1—C1—H1	108.8 (19)	H8A—C8—H8C	109 (3)
N1—C1—H1	110.8 (19)	H8B—C8—H8C	106 (3)
C2—C1—H1	112.0 (19)	O5—C9—O4	123.47 (16)
O2—C2—C3	106.33 (12)	O5—C9—C10	125.36 (16)
O2—C2—C1	108.08 (13)	O4—C9—C10	111.16 (15)
C3—C2—C1	111.06 (13)	C9—C10—H10A	105 (2)
O2—C2—H2	109.9 (19)	C9—C10—H10B	111 (2)
C3—C2—H2	112 (2)	H10A—C10—H10B	113 (3)
C1—C2—H2	110 (2)	C9—C10—H10C	109 (2)
O4—C3—C2	106.02 (12)	H10A—C10—H10C	106 (3)
O4—C3—C4	112.20 (13)	H10B—C10—H10C	113 (3)
C2—C3—C4	110.72 (12)	O7—C11—O6	123.38 (16)
O4—C3—H3	110 (2)	O7—C11—C12	126.85 (17)
C2—C3—H3	110.9 (19)	O6—C11—C12	109.77 (15)
C4—C3—H3	107.6 (18)	C11—C12—H12A	109 (2)
O6—C4—C3	110.16 (12)	C11—C12—H12B	114 (2)
O6—C4—C5	107.64 (12)	H12A—C12—H12B	105 (3)
C3—C4—C5	105.79 (12)	C11—C12—H12C	108 (2)
O6—C4—H4	109 (2)	H12A—C12—H12C	111 (3)
C3—C4—H4	112.8 (19)	H12B—C12—H12C	110 (3)
C5—C4—H4	111.8 (19)	O9—C13—O8	122.48 (17)
O1—C5—C6	110.29 (13)	O9—C13—C14	126.20 (18)
O1—C5—C4	106.16 (12)	O8—C13—C14	111.28 (16)
C6—C5—C4	115.92 (14)	C13—C14—H14A	107 (2)
O1—C5—H5	110.8 (18)	C13—C14—H14B	110 (2)
C6—C5—H5	108.3 (17)	H14A—C14—H14B	112 (3)
C4—C5—H5	105.3 (18)	C13—C14—H14C	111 (2)
O8—C6—C5	109.89 (13)	H14A—C14—H14C	109 (3)
O8—C6—H6A	111.2 (19)	H14B—C14—H14C	107 (3)
C5—C6—H6A	108.9 (18)