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The title compound, C15H24N4O7, crystallizes with great difficulty as fine hair-like crystals. It is a significant material, because it displays a weak internal hydrogen bond which may help with the interpretation of the secondary structure preferences of this class of compounds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803022451/cf6285sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803022451/cf6285Isup2.hkl
Contains datablock I

CCDC reference: 226978

Key indicators

  • Single-crystal X-ray study
  • T = 190 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.054
  • wR factor = 0.106
  • Data-to-parameter ratio = 9.0

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT063_ALERT_3_A Crystal Probably too Large for Beam Size ....... 12.30 mm
Author Response: Attempts at cutting the only other crystal resulted in its destruction. See text
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.83 Ratio
Author Response: The isopropyl group is almost certainly librating. A disordered model refined no better than large adps. Note also the very large proportion of weak reflections (20% with I< 2( \s I). See text

Alert level B CRYSS02_ALERT_3_B The value of _exptl_crystal_size_max is > 1.0 Maximum crystal size given = 12.300 PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.99 PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.36 Ratio PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... C16 PLAT411_ALERT_2_B Short Inter H...H Contact H101 .. H211 = 2.06 Ang. PLAT432_ALERT_2_B Short Inter X...Y Contact O19 .. C25 = 2.89 Ang.
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C16 - C17 = 1.42 Ang.
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 27.47 From the CIF: _reflns_number_total 2204 Count of symmetry unique reflns 2262 Completeness (_total/calc) 97.44% 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
2 ALERT level A = In general: serious problem 6 ALERT level B = Potentially serious problem 3 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 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1997); cell refinement: DENZO/SCALEPACK; data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Watkin et al., 2001); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS.

isopropyl 6-amino-2,5-anhydro-3,6-dideoxy-6-N-(2,5-anhydro-6- azido-3,6-dideoxy-L-arabino-hexonyl)-L-arabino-hexonate top
Crystal data top
C15H24N4O7F(000) = 396.000
Mr = 372.38Dx = 1.388 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 9.7238 (3) ÅCell parameters from 1985 reflections
b = 5.6312 (2) Åθ = 5–27°
c = 16.2836 (5) ŵ = 0.11 mm1
β = 92.0137 (14)°T = 190 K
V = 891.08 (5) Å3Plate, colourless
Z = 212.30 × 0.02 × 0.01 mm
Data collection top
Nonius KappaCCD
diffractometer
2204 reflections with I > 10σ(I)
Graphite monochromatorRint = 0.02
ω scansθmax = 27.5°, θmin = 5.2°
Absorption correction: multi-scan
(DENZO/SCALEPACK; Otwinowski & Minor, 1997)
h = 1212
Tmin = 0.5, Tmax = 0.99k = 77
3754 measured reflectionsl = 2121
2204 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)] = 0.054H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.106 w = 1/[σ2(F2) + (0.0472P)2 + 0.453P],
where P = (2max(Fo2,0) + Fc2)/3
S = 0.95(Δ/σ)max = 0.001
2204 reflectionsΔρmax = 0.51 e Å3
244 parametersΔρmin = 0.41 e Å3
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.7869 (4)0.6875 (7)1.4509 (2)0.0648
N20.8679 (3)0.5564 (6)1.43180 (14)0.0437
N30.9659 (3)0.4331 (6)1.41502 (16)0.0488
C40.9289 (3)0.2011 (7)1.37722 (18)0.0396
C50.9001 (3)0.2205 (6)1.28524 (16)0.0313
O60.7937 (2)0.3929 (4)1.26945 (11)0.0335
C70.6763 (3)0.2819 (6)1.22909 (16)0.0294
C80.6629 (3)0.3389 (5)1.13810 (16)0.0272
N90.7566 (2)0.4861 (5)1.10799 (13)0.0292
C100.7451 (3)0.5813 (6)1.02492 (15)0.0304
C110.8231 (3)0.4371 (5)0.96212 (15)0.0263
O120.80336 (19)0.5540 (4)0.8828 (1)0.0283
C130.6931 (3)0.4391 (6)0.83712 (15)0.0281
C140.7458 (3)0.3541 (6)0.75626 (16)0.0295
O150.64492 (19)0.2535 (6)0.71156 (12)0.0482
C160.6840 (4)0.1374 (8)0.6346 (2)0.0494
C170.6905 (7)0.112 (1)0.6489 (3)0.1037
C180.5769 (8)0.2126 (13)0.5716 (3)0.1270
O190.8610 (2)0.3760 (5)0.73379 (12)0.0434
C200.6441 (3)0.2354 (6)0.89128 (16)0.0336
C210.7685 (3)0.1897 (5)0.94767 (16)0.0294
O220.8731 (2)0.0606 (4)0.90686 (14)0.0388
O230.56542 (19)0.2547 (5)1.09749 (12)0.0372
C240.6935 (3)0.0168 (6)1.24604 (17)0.0314
C250.8494 (3)0.0147 (6)1.24915 (16)0.0289
O260.8910 (2)0.0483 (5)1.16649 (11)0.0347
H411.00590.08591.387420.0389*
H420.84380.14121.403310.0389*
H510.98810.26631.259140.0348*
H710.58850.34441.251210.0329*
H910.820 (4)0.543 (8)1.141 (2)0.0500*
H1010.78280.74651.025490.0331*
H1020.64540.58501.007570.0331*
H1110.92020.42710.984190.0300*
H1310.61390.54750.823760.0317*
H1610.77480.18770.61310.0564*
H1710.71620.1980.59800.1082*
H1720.76270.1400.69290.1082*
H1730.59970.1720.66750.1082*
H1810.59900.13690.51820.1274*
H1820.57530.38910.56500.1274*
H1830.48460.15660.58910.1274*
H2010.56270.28520.923230.0352*
H2020.61970.09160.857990.0352*
H2110.74480.09720.997550.0292*
H2210.846 (4)0.066 (9)0.894 (2)0.0500*
H2410.65130.02931.298820.0327*
H2420.65100.07901.200250.0327*
H2510.88490.15111.282870.0326*
H2610.978 (4)0.056 (8)1.170 (2)0.0500*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.079 (2)0.055 (2)0.0609 (19)0.005 (2)0.0149 (17)0.0162 (19)
N20.0605 (17)0.0453 (18)0.0254 (11)0.0068 (16)0.0017 (11)0.0054 (14)
N30.0494 (15)0.055 (2)0.0413 (14)0.0020 (16)0.0054 (12)0.0161 (16)
C40.0454 (16)0.041 (2)0.0322 (14)0.0037 (15)0.0065 (13)0.0049 (15)
C50.0341 (14)0.0315 (17)0.0285 (13)0.0002 (13)0.0033 (11)0.0038 (13)
O60.0438 (11)0.0263 (11)0.0302 (9)0.0016 (9)0.0022 (8)0.0033 (9)
C70.0286 (13)0.0311 (16)0.0289 (13)0.0014 (13)0.005 (1)0.0013 (13)
C80.0274 (12)0.0231 (15)0.0311 (13)0.0040 (12)0.002 (1)0.0013 (12)
N90.0364 (12)0.0257 (13)0.025 (1)0.0044 (11)0.0012 (9)0.0006 (11)
C100.0448 (15)0.0203 (14)0.0262 (12)0.0017 (13)0.0026 (11)0.0019 (12)
C110.0344 (13)0.0211 (14)0.0231 (12)0.0013 (12)0.002 (1)0.0048 (12)
O120.036 (1)0.023 (1)0.0248 (8)0.0057 (9)0.0018 (7)0.0026 (9)
C130.0256 (12)0.0293 (16)0.0293 (12)0.0011 (12)0.002 (1)0.0002 (13)
C140.0281 (13)0.0324 (16)0.0278 (12)0.0011 (13)0.003 (1)0.0032 (13)
O150.029 (1)0.084 (2)0.031 (1)0.0055 (13)0.0025 (8)0.0187 (13)
C160.0447 (18)0.075 (3)0.0286 (15)0.0109 (19)0.0036 (13)0.0156 (17)
C170.176 (6)0.068 (4)0.072 (3)0.043 (4)0.056 (3)0.003 (3)
C180.216 (7)0.107 (5)0.054 (3)0.069 (6)0.054 (3)0.031 (3)
O190.034 (1)0.0583 (16)0.039 (1)0.0136 (11)0.0081 (8)0.0092 (12)
C200.0341 (14)0.0351 (17)0.0319 (13)0.0096 (14)0.0030 (11)0.0046 (14)
C210.0394 (15)0.0207 (14)0.0287 (13)0.0032 (12)0.0080 (11)0.0017 (12)
O220.0518 (13)0.0227 (11)0.0426 (11)0.0034 (11)0.013 (1)0.0035 (11)
O230.030 (1)0.0418 (14)0.039 (1)0.004 (1)0.0040 (8)0.0028 (11)
C240.0319 (14)0.0300 (17)0.0324 (13)0.0029 (13)0.0044 (11)0.0049 (13)
C250.0305 (13)0.0268 (15)0.0295 (13)0.0027 (12)0.001 (1)0.0027 (13)
O260.0310 (9)0.0449 (14)0.0281 (9)0.003 (1)0.0012 (7)0.008 (1)
Geometric parameters (Å, º) top
N1—N21.131 (4)C13—C141.508 (4)
N2—N31.218 (4)C14—O191.197 (3)
N3—C41.483 (5)C14—O151.328 (3)
C4—H421.002O15—C161.475 (4)
C4—H411.000C16—H1611.002
C4—C51.518 (4)C16—C181.497 (6)
C5—H511.002C16—C171.424 (7)
C5—C251.524 (4)C17—H1731.002
C5—O61.436 (4)C17—H1720.998
O6—C71.440 (3)C17—H1710.999
C7—H711.002C18—H1831.002
C7—C241.527 (5)C18—H1820.999
C7—C81.517 (4)C18—H1810.999
C8—O231.232 (3)C20—H2020.999
C8—N91.337 (4)C20—H2011.002
N9—H910.86 (4)C20—C211.515 (4)
N9—C101.456 (3)C21—H2110.999
C10—H1021.001C21—O221.433 (4)
C10—H1011.000O22—H2210.78 (5)
C10—C111.528 (4)C24—H2420.998
C11—H1111.000C24—H2411.000
C11—C211.506 (4)C24—C251.526 (4)
C11—O121.456 (3)C25—H2510.999
O12—C131.437 (3)C25—O261.431 (3)
C13—H1311.000O26—H2610.85 (4)
C13—C201.533 (4)
N3—N2—N1172.6 (4)O19—C14—C13125.8 (3)
C4—N3—N2114.5 (3)O15—C14—C13110.3 (2)
H42—C4—H41109.6C16—O15—C14116.6 (2)
H42—C4—C5108.4H161—C16—C18106.3
H41—C4—C5108.7H161—C16—C17107.5
H42—C4—N3108.2C18—C16—C17114.6 (5)
H41—C4—N3109.5H161—C16—O15115.3
C5—C4—N3112.3 (3)C18—C16—O15105.2 (3)
H51—C5—C25109.2C17—C16—O15108.0 (4)
H51—C5—O6111.8H173—C17—H172109.6
C25—C5—O6107.3 (2)H173—C17—H171109.6
H51—C5—C4107.8H172—C17—H171109.2
C25—C5—C4111.3 (3)H173—C17—C16110.2
O6—C5—C4109.4 (2)H172—C17—C16107.4
C7—O6—C5110.1 (2)H171—C17—C16110.7
H71—C7—C24111.6H183—C18—H182109.4
H71—C7—C8103.4H183—C18—H181109.6
C24—C7—C8112.9 (2)H182—C18—H181109.5
H71—C7—O6110.8H183—C18—C16108.9
C24—C7—O6105.2 (2)H182—C18—C16111.3
C8—C7—O6113.1 (2)H181—C18—C16108.1
O23—C8—N9124.3 (2)H202—C20—H201109.4
O23—C8—C7118.7 (2)H202—C20—C21111.1
N9—C8—C7117.0 (2)H201—C20—C21111.2
H91—N9—C10118 (3)H202—C20—C13111.6
H91—N9—C8119 (3)H201—C20—C13110.9
C10—N9—C8122.6 (2)C21—C20—C13102.6 (2)
H102—C10—H101109.5H211—C21—O22107.5
H102—C10—C11108.7H211—C21—C11116.5
H101—C10—C11108.1O22—C21—C11106.9 (2)
H102—C10—N9108.1H211—C21—C20112.3
H101—C10—N9108.5O22—C21—C20111.7 (2)
C11—C10—N9113.8 (2)C11—C21—C20102.0 (2)
H111—C11—C21109.1H221—O22—C21110 (3)
H111—C11—O12116.0H242—C24—H241109.3
C21—C11—O12104.2 (2)H242—C24—C25110.3
H111—C11—C10105.9H241—C24—C25112.3
C21—C11—C10114.6 (2)H242—C24—C7110.7
O12—C11—C10107.5 (2)H241—C24—C7111.3
C13—O12—C11109.2 (2)C25—C24—C7102.8 (2)
H131—C13—C20109.2H251—C25—O26108.2
H131—C13—C14106.7H251—C25—C5110.8
C20—C13—C14112.8 (3)O26—C25—C5112.3 (2)
H131—C13—O12113.1H251—C25—C24115.6
C20—C13—O12106.3 (2)O26—C25—C24107.3 (2)
C14—C13—O12108.9 (2)C5—C25—C24102.7 (2)
O19—C14—O15123.9 (3)H261—O26—C25105 (2)
 

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