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The title compound, C10H15N3O13, is a derivative of the energetic compound penta­erythritol tetra­nitrate (PETN). It is a hapten (a small mol­ecule which can elicit an immune response only when coupled to a large carrier such as a protein) for PETN and was designed to be more stable and useful in immunochemistry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018411/fl2029sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018411/fl2029Isup2.hkl
Contains datablock I

CCDC reference: 610768

Key indicators

  • Single-crystal X-ray study
  • T = 306 K
  • Mean [sigma](C-C) = 0.002 Å
  • Disorder in main residue
  • R factor = 0.043
  • wR factor = 0.132
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.98 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N7 PLAT301_ALERT_3_C Main Residue Disorder ......................... 16.00 Perc. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 5.30 Deg. C2A -C1 -C2 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 1 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: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005) and XPREP (Bruker, 2001); 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.

Pentaerythritol trinitrate succinate top
Crystal data top
C10H15N3O13F(000) = 800
Mr = 385.25Dx = 1.537 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.3592 (9) ÅCell parameters from 1118 reflections
b = 11.9156 (10) Åθ = 2.6–26.1°
c = 13.4905 (11) ŵ = 0.15 mm1
β = 92.637 (1)°T = 306 K
V = 1663.5 (2) Å3Plate, colorless
Z = 40.46 × 0.35 × 0.08 mm
Data collection top
Bruker SMART APEX-II CCD
diffractometer
4028 independent reflections
Radiation source: fine-focus sealed tube2963 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ω scansθmax = 28.1°, θmin = 2.3°
Absorption correction: multi-scan
(TWINABS; Bruker, 2003)
h = 1313
Tmin = 0.936, Tmax = 0.989k = 1515
7689 measured reflectionsl = 017
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.25 w = 1/[σ2(Fo2) + (0.0658P)2]
where P = (Fo2 + 2Fc2)/3
4028 reflections(Δ/σ)max = 0.003
276 parametersΔρmax = 0.24 e Å3
8 restraintsΔρmin = 0.19 e Å3
Special details top

Experimental. Decay correction based on full (i.e. twinned) dataset consisting of 51045 reflections and 2573 equivalents over time used to determine the decay.

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.66792 (13)0.16667 (12)0.70113 (9)0.0392 (3)
C20.6652 (7)0.1661 (6)0.8168 (4)0.0453 (18)0.673 (16)
H2A0.58110.18910.83820.054*0.673 (16)
H2B0.68470.09200.84300.054*0.673 (16)
O30.7643 (10)0.2463 (8)0.8495 (5)0.0576 (18)0.673 (16)
N40.7935 (8)0.2392 (7)0.9504 (2)0.078 (2)0.673 (16)
O40.7132 (9)0.1861 (8)1.0010 (5)0.093 (2)0.673 (16)
O4'0.8768 (10)0.3032 (10)0.9761 (4)0.144 (3)0.673 (16)
C2A0.6714 (12)0.1560 (12)0.8109 (10)0.043 (3)0.327 (16)
H2AA0.58460.14900.83420.052*0.327 (16)
H2AB0.72080.09040.83200.052*0.327 (16)
O3A0.732 (2)0.2577 (17)0.8498 (10)0.060 (4)0.327 (16)
N4A0.7531 (12)0.2648 (9)0.9517 (8)0.086 (4)*0.327 (16)
O4A0.7636 (15)0.1654 (11)0.9931 (10)0.079 (3)0.327 (16)
O4B0.8125 (16)0.3457 (10)0.9780 (10)0.112 (4)0.327 (16)
C50.80146 (13)0.12840 (14)0.66994 (10)0.0448 (3)
H5A0.86880.17120.70500.054*
H5B0.81430.04950.68510.054*
O60.80551 (10)0.14710 (10)0.56424 (7)0.0504 (3)
N70.92841 (14)0.13775 (13)0.52746 (10)0.0581 (4)
O7'1.01292 (14)0.10376 (19)0.58251 (10)0.1013 (6)
O70.93322 (14)0.16550 (13)0.44252 (9)0.0779 (4)
C80.56085 (14)0.09001 (12)0.65865 (11)0.0466 (3)
H8A0.47660.12100.67140.056*
H8B0.56750.08150.58760.056*
O90.57847 (10)0.01702 (8)0.70795 (8)0.0486 (3)
N100.47722 (15)0.09157 (12)0.68768 (12)0.0609 (4)
O10'0.39650 (14)0.06608 (13)0.62542 (12)0.0836 (4)
O100.48580 (14)0.17410 (10)0.73902 (14)0.0870 (5)
C110.64075 (14)0.28536 (13)0.66194 (11)0.0464 (3)
H11A0.70960.33580.68420.056*
H11B0.63570.28520.59000.056*
O120.51993 (10)0.32176 (8)0.69940 (8)0.0495 (3)
C130.48627 (14)0.42864 (12)0.67899 (10)0.0412 (3)
O130.55590 (11)0.49160 (9)0.63719 (9)0.0601 (3)
C140.35646 (14)0.45552 (13)0.71725 (10)0.0435 (3)
H14A0.35700.43760.78740.052*
H14B0.29200.40840.68340.052*
C150.31788 (15)0.57775 (13)0.70310 (11)0.0472 (3)
H15A0.24420.59310.74290.057*
H15B0.38870.62480.72790.057*
C160.28353 (14)0.61033 (13)0.59673 (11)0.0474 (3)
H16A0.28180.69160.59210.057*
H16B0.35100.58360.55520.057*
C170.15711 (13)0.56562 (11)0.55702 (10)0.0394 (3)
O17'0.08165 (10)0.51459 (10)0.60732 (7)0.0509 (3)
O170.13294 (10)0.58726 (10)0.46251 (7)0.0542 (3)
H17A0.06650.55500.44340.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0389 (7)0.0421 (7)0.0365 (7)0.0013 (6)0.0007 (5)0.0080 (5)
C20.063 (4)0.042 (3)0.031 (2)0.007 (2)0.0020 (18)0.0118 (19)
O30.067 (4)0.068 (3)0.0372 (15)0.033 (3)0.0017 (16)0.0048 (14)
N40.104 (4)0.097 (3)0.0305 (14)0.049 (4)0.0124 (15)0.0047 (15)
O40.124 (5)0.112 (4)0.0444 (16)0.043 (3)0.007 (3)0.0115 (18)
O4'0.175 (6)0.194 (7)0.061 (2)0.124 (5)0.037 (3)0.010 (3)
C2A0.025 (4)0.044 (5)0.061 (7)0.015 (3)0.015 (4)0.017 (4)
O3A0.067 (9)0.070 (4)0.044 (3)0.025 (5)0.010 (3)0.003 (3)
O4A0.099 (7)0.102 (6)0.035 (3)0.034 (5)0.001 (4)0.013 (3)
O4B0.129 (8)0.124 (7)0.084 (5)0.068 (6)0.011 (5)0.036 (5)
C50.0430 (8)0.0526 (8)0.0384 (7)0.0035 (6)0.0032 (5)0.0079 (6)
O60.0467 (6)0.0663 (7)0.0380 (5)0.0079 (5)0.0006 (4)0.0032 (5)
N70.0572 (8)0.0700 (9)0.0476 (8)0.0099 (7)0.0077 (6)0.0047 (7)
O7'0.0596 (8)0.1795 (18)0.0648 (9)0.0421 (10)0.0028 (7)0.0094 (10)
O70.0895 (9)0.0992 (11)0.0463 (7)0.0126 (8)0.0175 (6)0.0015 (7)
C80.0436 (8)0.0487 (8)0.0469 (8)0.0026 (6)0.0048 (6)0.0085 (6)
O90.0494 (6)0.0392 (5)0.0566 (6)0.0038 (4)0.0039 (4)0.0012 (4)
N100.0547 (9)0.0443 (8)0.0840 (11)0.0070 (6)0.0087 (8)0.0117 (7)
O10'0.0612 (8)0.0812 (10)0.1062 (11)0.0156 (7)0.0190 (8)0.0118 (8)
O100.0861 (10)0.0408 (7)0.1349 (14)0.0090 (6)0.0160 (9)0.0077 (8)
C110.0434 (8)0.0467 (8)0.0496 (8)0.0022 (6)0.0082 (6)0.0124 (6)
O120.0468 (6)0.0429 (6)0.0598 (6)0.0043 (4)0.0120 (5)0.0140 (4)
C130.0412 (7)0.0413 (7)0.0404 (7)0.0021 (6)0.0068 (5)0.0046 (6)
O130.0498 (6)0.0483 (6)0.0829 (8)0.0017 (5)0.0098 (6)0.0192 (6)
C140.0429 (8)0.0475 (8)0.0398 (7)0.0008 (6)0.0023 (6)0.0054 (6)
C150.0448 (8)0.0464 (8)0.0495 (8)0.0000 (6)0.0061 (6)0.0051 (6)
C160.0424 (8)0.0438 (8)0.0552 (8)0.0022 (6)0.0055 (6)0.0098 (6)
C170.0365 (7)0.0386 (7)0.0430 (7)0.0048 (6)0.0012 (5)0.0025 (6)
O17'0.0408 (5)0.0665 (7)0.0452 (6)0.0074 (5)0.0009 (4)0.0065 (5)
O170.0479 (6)0.0690 (7)0.0451 (6)0.0144 (5)0.0047 (4)0.0095 (5)
Geometric parameters (Å, º) top
C1—C2A1.485 (14)C8—H8A0.9700
C1—C81.528 (2)C8—H8B0.9700
C1—C51.534 (2)O9—N101.3919 (17)
C1—C111.531 (2)N10—O10'1.197 (2)
C1—C21.562 (6)N10—O101.204 (2)
C2—O31.456 (7)C11—O121.4381 (17)
C2—H2A0.9700C11—H11A0.9700
C2—H2B0.9700C11—H11B0.9700
O3—N41.384 (6)O12—C131.3456 (17)
N4—O4'1.191 (5)C13—O131.1994 (17)
N4—O41.269 (7)C13—C141.497 (2)
C2A—O3A1.453 (14)C14—C151.520 (2)
C2A—H2AA0.9700C14—H14A0.9700
C2A—H2AB0.9700C14—H14B0.9700
O3A—N4A1.385 (12)C15—C161.513 (2)
N4A—O4B1.189 (12)C15—H15A0.9700
N4A—O4A1.311 (13)C15—H15B0.9700
C5—O61.4457 (16)C16—C171.490 (2)
C5—H5A0.9700C16—H16A0.9700
C5—H5B0.9700C16—H16B0.9700
O6—N71.3921 (17)C17—O17'1.2207 (16)
N7—O7'1.1926 (19)C17—O171.3135 (16)
N7—O71.1959 (18)O17—H17A0.8200
C8—O91.4461 (18)
C2A—C1—C8107.9 (4)O9—C8—H8A110.5
C2A—C1—C5105.5 (6)C1—C8—H8A110.5
C8—C1—C5111.57 (12)O9—C8—H8B110.5
C2A—C1—C11114.8 (6)C1—C8—H8B110.5
C8—C1—C11107.69 (11)H8A—C8—H8B108.7
C5—C1—C11109.49 (11)N10—O9—C8113.23 (11)
C2A—C1—C25.3 (9)O10'—N10—O10129.92 (16)
C8—C1—C2109.0 (2)O10'—N10—O9118.15 (15)
C5—C1—C2109.3 (3)O10—N10—O9111.92 (16)
C11—C1—C2109.7 (3)O12—C11—C1107.84 (11)
O3—C2—C1104.8 (4)O12—C11—H11A110.1
O3—C2—H2A110.8C1—C11—H11A110.1
C1—C2—H2A110.8O12—C11—H11B110.1
O3—C2—H2B110.8C1—C11—H11B110.1
C1—C2—H2B110.8H11A—C11—H11B108.5
H2A—C2—H2B108.9C13—O12—C11115.79 (11)
N4—O3—C2112.2 (6)O13—C13—O12122.16 (14)
O4'—N4—O4130.3 (5)O13—C13—C14126.69 (13)
O4'—N4—O3111.7 (5)O12—C13—C14111.13 (12)
O4—N4—O3116.1 (6)C13—C14—C15113.38 (12)
O3A—C2A—C1106.2 (9)C13—C14—H14A108.9
O3A—C2A—H2AA110.5C15—C14—H14A108.9
C1—C2A—H2AA110.5C13—C14—H14B108.9
O3A—C2A—H2AB110.5C15—C14—H14B108.9
C1—C2A—H2AB110.5H14A—C14—H14B107.7
H2AA—C2A—H2AB108.7C16—C15—C14114.46 (12)
N4A—O3A—C2A117.0 (14)C16—C15—H15A108.6
O4B—N4A—O4A125.0 (12)C14—C15—H15A108.6
O4B—N4A—O3A113.5 (12)C16—C15—H15B108.6
O4A—N4A—O3A111.9 (12)C14—C15—H15B108.6
O6—C5—C1106.99 (10)H15A—C15—H15B107.6
O6—C5—H5A110.3C17—C16—C15114.43 (12)
C1—C5—H5A110.3C17—C16—H16A108.7
O6—C5—H5B110.3C15—C16—H16A108.7
C1—C5—H5B110.3C17—C16—H16B108.7
H5A—C5—H5B108.6C15—C16—H16B108.7
N7—O6—C5114.06 (10)H16A—C16—H16B107.6
O7'—N7—O7128.97 (15)O17'—C17—O17122.62 (13)
O7'—N7—O6117.54 (13)O17'—C17—C16123.56 (13)
O7—N7—O6113.49 (13)O17—C17—C16113.82 (12)
O9—C8—C1106.30 (11)C17—O17—H17A109.5
C2A—C1—C2—O3105 (7)C2A—C1—C8—O947.5 (7)
C8—C1—C2—O3176.5 (6)C5—C1—C8—O967.92 (14)
C5—C1—C2—O361.2 (7)C11—C1—C8—O9171.91 (11)
C11—C1—C2—O358.8 (7)C2—C1—C8—O952.9 (3)
C1—C2—O3—N4167.4 (8)C1—C8—O9—N10171.33 (11)
C2—O3—N4—O4'178.3 (8)C8—O9—N10—O10'8.2 (2)
C2—O3—N4—O415.5 (14)C8—O9—N10—O10171.15 (14)
C8—C1—C2A—O3A157.5 (12)C2A—C1—C11—O1257.0 (5)
C5—C1—C2A—O3A83.1 (14)C8—C1—C11—O1263.16 (15)
C11—C1—C2A—O3A37.5 (14)C5—C1—C11—O12175.35 (11)
C2—C1—C2A—O3A54 (6)C2—C1—C11—O1255.4 (3)
C1—C2A—O3A—N4A176.7 (15)C1—C11—O12—C13174.56 (12)
C2A—O3A—N4A—O4B174.3 (15)C11—O12—C13—O134.1 (2)
C2A—O3A—N4A—O4A26 (2)C11—O12—C13—C14177.31 (11)
C2A—C1—C5—O6175.0 (5)O13—C13—C14—C152.8 (2)
C8—C1—C5—O668.09 (14)O12—C13—C14—C15175.68 (12)
C11—C1—C5—O651.02 (16)C13—C14—C15—C1671.83 (16)
C2—C1—C5—O6171.2 (3)C14—C15—C16—C1772.66 (17)
C1—C5—O6—N7167.87 (12)C15—C16—C17—O17'5.7 (2)
C5—O6—N7—O7'8.2 (2)C15—C16—C17—O17175.09 (12)
C5—O6—N7—O7172.13 (14)
 

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