2-Azido-2-de­oxy-2,4-C-dimethyl-3,4-O-isopropyl­idene-L-ribono-1,5-lactone

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.

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

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Computing details

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

Crystal data

C10H15N3O4	Dx = 1.359 Mg m^−3
Mr = 241.25	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1568 reflections
a = 6.2165 (1) Å	θ = 5–27°
b = 9.7821 (2) Å	µ = 0.11 mm^−1
c = 19.3880 (5) Å	T = 150 K
V = 1178.99 (4) Å^3	Plate, colourless
Z = 4	0.50 × 0.10 × 0.05 mm
F(000) = 512

Data collection

Nonius KappaCCD area-detector diffractometer	1279 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
ω scans	θmax = 27.4°, θmin = 5.2°
Absorption correction: multi-scan DENZO and SCALEPACK (Otwinowski & Minor, 1997)	h = −8→8
Tmin = 0.90, Tmax = 0.99	k = −12→12
18956 measured reflections	l = −24→25
1552 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.073	w = 1/[σ^2(F^2) + (0.04P)^2 + 0.14P], where P = [max(Fo^2,0) + 2Fc^2]/3
S = 0.92	(Δ/σ)max = 0.000294
1552 reflections	Δρmax = 0.23 e Å^−3
154 parameters	Δρmin = −0.21 e Å^−3
0 restraints

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

	x	y	z	Uiso*/Ueq
C1	0.2285 (3)	0.55253 (17)	0.29727 (9)	0.0256
C2	0.3392 (3)	0.50533 (16)	0.36370 (8)	0.0250
C3	0.2553 (3)	0.36633 (17)	0.39117 (9)	0.0263
O4	0.2024 (2)	0.39663 (11)	0.46208 (6)	0.0300
C5	0.2861 (3)	0.52729 (17)	0.47991 (8)	0.0302
O6	0.2846 (2)	0.60142 (11)	0.41612 (5)	0.0273
C7	0.1332 (4)	0.5957 (2)	0.52936 (10)	0.0424
C8	0.5142 (3)	0.5160 (2)	0.50750 (10)	0.0449
C9	0.0479 (3)	0.32281 (17)	0.35639 (10)	0.0299
O10	−0.09452 (18)	0.43543 (12)	0.34044 (6)	0.0307
C11	−0.0156 (3)	0.54661 (17)	0.30818 (9)	0.0262
O12	−0.1382 (2)	0.63484 (13)	0.29069 (7)	0.0361
C13	0.4179 (3)	0.25119 (18)	0.38671 (10)	0.0358
N14	0.2947 (2)	0.69295 (14)	0.27860 (7)	0.0289
N15	0.2285 (2)	0.78922 (15)	0.31426 (7)	0.0291
N16	0.1835 (3)	0.88907 (16)	0.33958 (8)	0.0410
C17	0.3008 (3)	0.46816 (18)	0.23473 (8)	0.0339
H21	0.4979	0.5028	0.3566	0.0300*
H71	0.1890	0.6845	0.5417	0.0617*
H72	0.1280	0.5389	0.5712	0.0622*
H73	−0.0110	0.6036	0.5084	0.0624*
H81	0.5607	0.6065	0.5227	0.0669*
H82	0.5167	0.4542	0.5470	0.0673*
H83	0.6127	0.4825	0.4718	0.0674*
H91	−0.0306	0.2640	0.3894	0.0369*
H92	0.0809	0.2734	0.3125	0.0376*
H131	0.3511	0.1657	0.4016	0.0530*
H132	0.5402	0.2727	0.4163	0.0534*
H133	0.4648	0.2404	0.3383	0.0536*
H171	0.2227	0.5022	0.1936	0.0503*
H172	0.4540	0.4839	0.2297	0.0505*
H173	0.2677	0.3710	0.2433	0.0493*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0259 (9)	0.0222 (8)	0.0288 (8)	−0.0018 (8)	0.0038 (8)	0.0023 (7)
C2	0.0219 (8)	0.0238 (8)	0.0294 (8)	−0.0006 (8)	0.0015 (7)	0.0010 (7)
C3	0.0267 (9)	0.0251 (8)	0.0272 (8)	0.0005 (8)	0.0013 (8)	0.0032 (7)
O4	0.0361 (7)	0.0270 (6)	0.0269 (6)	−0.0045 (6)	0.0024 (5)	0.0024 (5)
C5	0.0373 (10)	0.0279 (9)	0.0255 (8)	−0.0049 (9)	−0.0046 (8)	0.0059 (7)
O6	0.0334 (7)	0.0237 (6)	0.0249 (6)	−0.0017 (6)	−0.0027 (6)	0.0025 (5)
C7	0.0593 (13)	0.0366 (10)	0.0312 (9)	−0.0036 (11)	0.0049 (10)	−0.0012 (8)
C8	0.0530 (12)	0.0408 (11)	0.0408 (11)	−0.0063 (11)	−0.0179 (10)	0.0078 (10)
C9	0.0301 (9)	0.0235 (8)	0.0361 (9)	−0.0022 (8)	0.0008 (8)	0.0024 (8)
O10	0.0235 (6)	0.0286 (6)	0.0399 (6)	−0.0014 (6)	−0.0005 (6)	0.0063 (6)
C11	0.0280 (9)	0.0267 (8)	0.0240 (8)	−0.0013 (8)	−0.0017 (8)	−0.0003 (8)
O12	0.0291 (7)	0.0358 (7)	0.0434 (7)	0.0039 (6)	−0.0028 (6)	0.0073 (6)
C13	0.0339 (9)	0.0277 (9)	0.0459 (10)	0.0054 (9)	0.0033 (9)	0.0046 (9)
N14	0.0330 (8)	0.0260 (7)	0.0276 (7)	−0.0027 (7)	0.0056 (7)	0.0021 (6)
N15	0.0313 (8)	0.0287 (8)	0.0273 (7)	−0.0055 (7)	0.0026 (7)	0.0055 (7)
N16	0.0546 (10)	0.0283 (8)	0.0401 (9)	0.0005 (9)	0.0089 (9)	−0.0024 (7)
C17	0.0383 (10)	0.0329 (10)	0.0306 (9)	0.0001 (9)	0.0091 (9)	−0.0007 (8)

Geometric parameters (Å, º)

C1—C2	1.532 (2)	C8—H81	0.977
C1—C11	1.533 (2)	C8—H82	0.976
C1—N14	1.479 (2)	C8—H83	0.981
C1—C17	1.534 (2)	C9—O10	1.447 (2)
C2—C3	1.551 (2)	C9—H91	0.989
C2—O6	1.4254 (19)	C9—H92	0.999
C2—H21	0.996	O10—C11	1.347 (2)
C3—O4	1.444 (2)	C11—O12	1.200 (2)
C3—C9	1.516 (2)	C13—H131	0.977
C3—C13	1.516 (2)	C13—H132	0.976
O4—C5	1.422 (2)	C13—H133	0.988
C5—O6	1.4338 (19)	N14—N15	1.239 (2)
C5—C7	1.506 (3)	N15—N16	1.128 (2)
C5—C8	1.520 (3)	C17—H171	0.992
C7—H71	0.966	C17—H172	0.970
C7—H72	0.985	C17—H173	0.986
C7—H73	0.987
C2—C1—C11	108.51 (14)	H72—C7—H73	110.7
C2—C1—N14	111.14 (14)	C5—C8—H81	108.4
C11—C1—N14	110.15 (14)	C5—C8—H82	109.6
C2—C1—C17	111.76 (13)	H81—C8—H82	108.7
C11—C1—C17	112.25 (15)	C5—C8—H83	111.0
N14—C1—C17	102.97 (13)	H81—C8—H83	109.4
C1—C2—C3	113.71 (14)	H82—C8—H83	109.7
C1—C2—O6	107.08 (12)	C3—C9—O10	113.69 (13)
C3—C2—O6	104.67 (12)	C3—C9—H91	107.2
C1—C2—H21	109.7	O10—C9—H91	106.2
C3—C2—H21	111.0	C3—C9—H92	109.8
O6—C2—H21	110.5	O10—C9—H92	108.2
C2—C3—O4	102.92 (13)	H91—C9—H92	111.7
C2—C3—C9	112.30 (14)	C9—O10—C11	119.43 (13)
O4—C3—C9	106.70 (14)	C1—C11—O10	117.05 (15)
C2—C3—C13	114.07 (13)	C1—C11—O12	124.19 (16)
O4—C3—C13	111.02 (14)	O10—C11—O12	118.75 (15)
C9—C3—C13	109.45 (14)	C3—C13—H131	109.6
C3—O4—C5	109.42 (13)	C3—C13—H132	109.0
O4—C5—O6	104.03 (12)	H131—C13—H132	110.0
O4—C5—C7	108.85 (15)	C3—C13—H133	109.3
O6—C5—C7	108.69 (14)	H131—C13—H133	108.3
O4—C5—C8	111.17 (15)	H132—C13—H133	110.6
O6—C5—C8	110.26 (14)	C1—N14—N15	118.48 (13)
C7—C5—C8	113.39 (16)	N14—N15—N16	169.52 (16)
C5—O6—C2	106.27 (11)	C1—C17—H171	108.2
C5—C7—H71	109.3	C1—C17—H172	106.4
C5—C7—H72	107.2	H171—C17—H172	110.3
H71—C7—H72	108.4	C1—C17—H173	108.9
C5—C7—H73	110.3	H171—C17—H173	110.9
H71—C7—H73	110.9	H172—C17—H173	112.0