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The relative configuration of the title lactone, C10H15N3O4, a compound of value in the synthesis of complex pyrrolidines, was determined by X-ray crystallographic analysis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807010598/fl2104sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807010598/fl2104Isup2.hkl
Contains datablock I

CCDC reference: 642984

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.032
  • wR factor = 0.073
  • Data-to-parameter ratio = 10.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N14 - N15 .. 6.08 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N15 - N16 .. 5.27 su
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 27.41 From the CIF: _reflns_number_total 1552 Count of symmetry unique reflns 1569 Completeness (_total/calc) 98.92% 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 PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and 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.

2-Azido-2-deoxy-2,4-C-dimethyl-3,4-O-isopropylidene-L-ribono- 1,5-lactone top
Crystal data top
C10H15N3O4Dx = 1.359 Mg m3
Mr = 241.25Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 1568 reflections
a = 6.2165 (1) Åθ = 5–27°
b = 9.7821 (2) ŵ = 0.11 mm1
c = 19.3880 (5) ÅT = 150 K
V = 1178.99 (4) Å3Plate, colourless
Z = 40.50 × 0.10 × 0.05 mm
F(000) = 512
Data collection top
Nonius KappaCCD area-detector
diffractometer
1279 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
ω scansθmax = 27.4°, θmin = 5.2°
Absorption correction: multi-scan
DENZO and SCALEPACK (Otwinowski & Minor, 1997)
h = 88
Tmin = 0.90, Tmax = 0.99k = 1212
18956 measured reflectionsl = 2425
1552 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.073 w = 1/[σ2(F2) + (0.04P)2 + 0.14P],
where P = [max(Fo2,0) + 2Fc2]/3
S = 0.92(Δ/σ)max = 0.000294
1552 reflectionsΔρmax = 0.23 e Å3
154 parametersΔρmin = 0.21 e Å3
0 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2285 (3)0.55253 (17)0.29727 (9)0.0256
C20.3392 (3)0.50533 (16)0.36370 (8)0.0250
C30.2553 (3)0.36633 (17)0.39117 (9)0.0263
O40.2024 (2)0.39663 (11)0.46208 (6)0.0300
C50.2861 (3)0.52729 (17)0.47991 (8)0.0302
O60.2846 (2)0.60142 (11)0.41612 (5)0.0273
C70.1332 (4)0.5957 (2)0.52936 (10)0.0424
C80.5142 (3)0.5160 (2)0.50750 (10)0.0449
C90.0479 (3)0.32281 (17)0.35639 (10)0.0299
O100.09452 (18)0.43543 (12)0.34044 (6)0.0307
C110.0156 (3)0.54661 (17)0.30818 (9)0.0262
O120.1382 (2)0.63484 (13)0.29069 (7)0.0361
C130.4179 (3)0.25119 (18)0.38671 (10)0.0358
N140.2947 (2)0.69295 (14)0.27860 (7)0.0289
N150.2285 (2)0.78922 (15)0.31426 (7)0.0291
N160.1835 (3)0.88907 (16)0.33958 (8)0.0410
C170.3008 (3)0.46816 (18)0.23473 (8)0.0339
H210.49790.50280.35660.0300*
H710.18900.68450.54170.0617*
H720.12800.53890.57120.0622*
H730.01100.60360.50840.0624*
H810.56070.60650.52270.0669*
H820.51670.45420.54700.0673*
H830.61270.48250.47180.0674*
H910.03060.26400.38940.0369*
H920.08090.27340.31250.0376*
H1310.35110.16570.40160.0530*
H1320.54020.27270.41630.0534*
H1330.46480.24040.33830.0536*
H1710.22270.50220.19360.0503*
H1720.45400.48390.22970.0505*
H1730.26770.37100.24330.0493*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0259 (9)0.0222 (8)0.0288 (8)0.0018 (8)0.0038 (8)0.0023 (7)
C20.0219 (8)0.0238 (8)0.0294 (8)0.0006 (8)0.0015 (7)0.0010 (7)
C30.0267 (9)0.0251 (8)0.0272 (8)0.0005 (8)0.0013 (8)0.0032 (7)
O40.0361 (7)0.0270 (6)0.0269 (6)0.0045 (6)0.0024 (5)0.0024 (5)
C50.0373 (10)0.0279 (9)0.0255 (8)0.0049 (9)0.0046 (8)0.0059 (7)
O60.0334 (7)0.0237 (6)0.0249 (6)0.0017 (6)0.0027 (6)0.0025 (5)
C70.0593 (13)0.0366 (10)0.0312 (9)0.0036 (11)0.0049 (10)0.0012 (8)
C80.0530 (12)0.0408 (11)0.0408 (11)0.0063 (11)0.0179 (10)0.0078 (10)
C90.0301 (9)0.0235 (8)0.0361 (9)0.0022 (8)0.0008 (8)0.0024 (8)
O100.0235 (6)0.0286 (6)0.0399 (6)0.0014 (6)0.0005 (6)0.0063 (6)
C110.0280 (9)0.0267 (8)0.0240 (8)0.0013 (8)0.0017 (8)0.0003 (8)
O120.0291 (7)0.0358 (7)0.0434 (7)0.0039 (6)0.0028 (6)0.0073 (6)
C130.0339 (9)0.0277 (9)0.0459 (10)0.0054 (9)0.0033 (9)0.0046 (9)
N140.0330 (8)0.0260 (7)0.0276 (7)0.0027 (7)0.0056 (7)0.0021 (6)
N150.0313 (8)0.0287 (8)0.0273 (7)0.0055 (7)0.0026 (7)0.0055 (7)
N160.0546 (10)0.0283 (8)0.0401 (9)0.0005 (9)0.0089 (9)0.0024 (7)
C170.0383 (10)0.0329 (10)0.0306 (9)0.0001 (9)0.0091 (9)0.0007 (8)
Geometric parameters (Å, º) top
C1—C21.532 (2)C8—H810.977
C1—C111.533 (2)C8—H820.976
C1—N141.479 (2)C8—H830.981
C1—C171.534 (2)C9—O101.447 (2)
C2—C31.551 (2)C9—H910.989
C2—O61.4254 (19)C9—H920.999
C2—H210.996O10—C111.347 (2)
C3—O41.444 (2)C11—O121.200 (2)
C3—C91.516 (2)C13—H1310.977
C3—C131.516 (2)C13—H1320.976
O4—C51.422 (2)C13—H1330.988
C5—O61.4338 (19)N14—N151.239 (2)
C5—C71.506 (3)N15—N161.128 (2)
C5—C81.520 (3)C17—H1710.992
C7—H710.966C17—H1720.970
C7—H720.985C17—H1730.986
C7—H730.987
C2—C1—C11108.51 (14)H72—C7—H73110.7
C2—C1—N14111.14 (14)C5—C8—H81108.4
C11—C1—N14110.15 (14)C5—C8—H82109.6
C2—C1—C17111.76 (13)H81—C8—H82108.7
C11—C1—C17112.25 (15)C5—C8—H83111.0
N14—C1—C17102.97 (13)H81—C8—H83109.4
C1—C2—C3113.71 (14)H82—C8—H83109.7
C1—C2—O6107.08 (12)C3—C9—O10113.69 (13)
C3—C2—O6104.67 (12)C3—C9—H91107.2
C1—C2—H21109.7O10—C9—H91106.2
C3—C2—H21111.0C3—C9—H92109.8
O6—C2—H21110.5O10—C9—H92108.2
C2—C3—O4102.92 (13)H91—C9—H92111.7
C2—C3—C9112.30 (14)C9—O10—C11119.43 (13)
O4—C3—C9106.70 (14)C1—C11—O10117.05 (15)
C2—C3—C13114.07 (13)C1—C11—O12124.19 (16)
O4—C3—C13111.02 (14)O10—C11—O12118.75 (15)
C9—C3—C13109.45 (14)C3—C13—H131109.6
C3—O4—C5109.42 (13)C3—C13—H132109.0
O4—C5—O6104.03 (12)H131—C13—H132110.0
O4—C5—C7108.85 (15)C3—C13—H133109.3
O6—C5—C7108.69 (14)H131—C13—H133108.3
O4—C5—C8111.17 (15)H132—C13—H133110.6
O6—C5—C8110.26 (14)C1—N14—N15118.48 (13)
C7—C5—C8113.39 (16)N14—N15—N16169.52 (16)
C5—O6—C2106.27 (11)C1—C17—H171108.2
C5—C7—H71109.3C1—C17—H172106.4
C5—C7—H72107.2H171—C17—H172110.3
H71—C7—H72108.4C1—C17—H173108.9
C5—C7—H73110.3H171—C17—H173110.9
H71—C7—H73110.9H172—C17—H173112.0
 

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