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The title compound, C6H26N4O10, was synthesized as part of the Office of Naval Research Energetic Materials Research Program. When first studied in the mid-1980s, a solution was obtained which had two mol­ecules in the asymmetric unit, one of which was severely disordered. A new look at this compound in 2002 has revealed a structure with six mol­ecules in the asymmetric unit with no disorder. Five of the six unique mol­ecules are essentially identical. This deceptively simple mol­ecule presents an interesting case study to show how much data-collection hardware and software have improved since the middle-1980s.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802014101/cv6131sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802014101/cv6131Isup2.hkl
Contains datablock I

CCDC reference: 197479

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.049
  • wR factor = 0.130
  • Data-to-parameter ratio = 12.1

checkCIF results

No syntax errors found


Amber Alert Alert Level B:
PLAT_112 Alert B ADDSYM Detects Additional (Pseudo) Symm. Elem. S
Author response: This compound was originally solved in a cell 1/3 the size of the reported here. In the small cell there was disorder and it did not refine well. Data collected recently indicated a much larger cell and in this cell there is no disorder. The comment section discusses this situation in detail.
PLAT_112  Alert B ADDSYM Detects Additional (Pseudo) Symm. Elem.          S
Author response: This compound was originally solved in a cell 1/3 the size of the reported here. In the small cell there was disorder and it did not refine well. Data collected recently indicated a much larger cell and in this cell there is no disorder. The comment section discusses this situation in detail.
General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.30 From the CIF: _reflns_number_total 13028 Count of symmetry unique reflns 8279 Completeness (_total/calc) 157.36% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 4749 Fraction of Friedel pairs measured 0.574 Are heavy atom types Z>Si present no ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases.
0 Alert Level A = Potentially serious problem
2 Alert Level B = Potential problem
0 Alert Level C = Please check

Comment top

Data on 4,4,8,8-tetranitro-2,6-dioxabicyclo[3.3.0]octane (TNBO), (I) (Fig. 1), were originally collected in 1984 on what was then a Nicolet P3F diffractometer using Cu Kα radiation. The monoclinic unit cell was a = 9.631 (1) Å, b = 11.538 (20) Å, c = 10.205 (1) Å and β = 105.30 (1)°. The structure was solved, with difficulty, in space group P21 and refined to an R factor of 0.042 for the 1160 observed reflections (R for all 1601 unique data was 0.063). There were two molecules in the asymmetric unit, one of which was disordered (Fig. 2). The structure answered the questions posed by the chemist who synthesized the material. TNBO was the expected product and the solid-state density was 1.847. However, crystallographically, the results were unsatisfactory. Many constraints were required to keep the bond lengths and angles chemically reasonable, and a number of atoms required constraints to prevent the anisotropic displacement parameters from going negative during the refinement. Results were essentially the same for at least three different crystals from the same sample. The results were filed away and forgotten.

The availability of more powerful data-collection systems prompted a reinvestigation of this problem in 2002. Fortunately, the material was still available so we decided to grow new crystals and try again. This time, data were collected on a Bruker SMART 1000 CCD with Mo Kα radiation at 93 K. The autoindexing routine selected a similar, but different, cell from that obtained in 1984. The new cell had a volume three times larger than that of the original cell. In this `super' cell, two thirds of the data were quite weak, but too strong to be ignored. The distribution of intensities also made it difficult for direct-methods programs to solve the structure automatically. A partial structure was obtained using SnB (Weeks & Miller, 1999), which was developed into the full structure using difference Fourier maps (Fig. 3).

There are six molecules in the asymmetric unit with no disorder. There is a cis junction between the two five-membered rings, both of which have normal envelope conformations, with C7 and C5 being the flap atoms. Five of the six unique molecules are essentially identical (Fig. 3). In the sixth molecule, the envelope flips for one of the two five-membered rings, such that atom C7 is on the opposite side of the plane formed by the other four ring atoms, and, as a result, the two nitro groups on C8 are also displaced from the positions they occupy in the other five molecules. In the small cell, the non-disordered molecule and the major component of the disordered molecule have the same conformation and the disorder is present at ~18%, which correlates quite well with the finding of one molecule of six being different in the larger cell.

Now that the correct structure is in hand, it is obvious that two-thirds of the data were missed in 1984. An examination of the new data set clearly shows why that happened. Fig. 4 shows the density distribution in the h3l layer. The transformation from the smaller cell to the larger, (1 0 0, 0 1 0, 1 0 3), is more complicated than a simple tripling of the l axis. However, the regular pattern of strong and weak data is obvious in Fig. 4. Once this pattern was understood, it was possible to calculate the average intensities for both the strong and weak data within each layer (Fig. 5). On average, the strong data were approximately eight times more intense than the weak data. It is not surprising that the larger cell went undiscovered in 1984.

Experimental top

Crystals of (I) were grown from 2-butanone octane. The sample was provided by Kurt Baum of Fluorochem, Inc.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SnB (Weeks & Miller, 1999); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001) and MidasPlus (Ferrin et al., 1988; Huang et al., 1991); software used to prepare material for publication: SHELXTL (Bruker, 2001) and XPREP (Bruker, 2001).

Figures top
[Figure 1] Fig. 1. A view of one molecule of TNBO, with displacement ellipsoids at the 50% probability level (from the 2002 data set).
[Figure 2] Fig. 2. The disordered molecule of TNBO from the small unit cell of the 1984 determination. Displacement ellipsoids are at the 20% probability level. Anisotropic displacement parameters for six atoms (C1', C5', C8' O6', N8B' and O8D') were constrained to be approximately isotropic.
[Figure 3] Fig. 3. The asymmetric unit of TNBO, in the larger `true' cell, with displacement ellipsoids at the 50% probability level.
[Figure 4] Fig. 4. Relative intensity plot for the k = 3 layer in TNBO. The circles represent 1.5 and 1.0 Å resolution, +l is down and +h is to the right. The plot was generated by XPREP (Bruker 2001). The blue diagonal lines were added to highlight the strong intensities that led to the smaller cell in 1984.
[Figure 5] Fig. 5. Intensity distribution for the TNBO CCD data. The blue line shows the distribution for the strong data and the red line is the intensity distribution for the remaining two-thirds data set (i.e. the weak data).
4,4,8,8-Tetranitro-2,6-dioxabicyclo[3.3.0]octane top
Crystal data top
C6H6N4O10F(000) = 1800
Mr = 294.15Dx = 1.847 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 9.5746 (9) ÅCell parameters from 7125 reflections
b = 11.347 (1) Åθ = 2.3–28.3°
c = 29.241 (3) ŵ = 0.18 mm1
β = 92.546 (2)°T = 93 K
V = 3173.8 (5) Å3Irregular, colorless
Z = 120.45 × 0.22 × 0.12 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
13028 independent reflections
Radiation source: normal focus sealed tube10983 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ϕ and ω scansθmax = 28.3°, θmin = 1.4°
Absorption correction: integration
(SHELXTL; Bruker 2001)
h = 1212
Tmin = 0.922, Tmax = 0.979k = 1414
25608 measured reflectionsl = 3538
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 0.89 w = 1/[σ2(Fo2) + (0.098P)2 + 0.5756P]
where P = (Fo2 + 2Fc2)/3
13028 reflections(Δ/σ)max = 0.001
1081 parametersΔρmax = 0.52 e Å3
1 restraintΔρmin = 0.26 e Å3
Crystal data top
C6H6N4O10V = 3173.8 (5) Å3
Mr = 294.15Z = 12
Monoclinic, P21Mo Kα radiation
a = 9.5746 (9) ŵ = 0.18 mm1
b = 11.347 (1) ÅT = 93 K
c = 29.241 (3) Å0.45 × 0.22 × 0.12 mm
β = 92.546 (2)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
13028 independent reflections
Absorption correction: integration
(SHELXTL; Bruker 2001)
10983 reflections with I > 2σ(I)
Tmin = 0.922, Tmax = 0.979Rint = 0.029
25608 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0491 restraint
wR(F2) = 0.130H-atom parameters constrained
S = 0.89Δρmax = 0.52 e Å3
13028 reflectionsΔρmin = 0.26 e Å3
1081 parameters
Special details top

Experimental. Final cell refinement and decay correction, if needed, applied after integration as part of merge process in SAINT v6.02 A.

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*/Ueq
C10.7474 (3)0.7821 (2)0.96469 (9)0.0111 (5)
H1A0.76890.77380.93240.013*
O20.7411 (2)0.90256 (17)0.97859 (7)0.0145 (4)
C30.6165 (3)0.9248 (3)1.00244 (9)0.0156 (6)
H3A0.58091.00330.99580.019*
H3B0.63360.91691.03520.019*
C40.5143 (3)0.8310 (2)0.98434 (9)0.0115 (5)
N4A0.3999 (2)0.8012 (2)1.01641 (8)0.0170 (5)
O4A0.3914 (2)0.8608 (2)1.05046 (7)0.0284 (5)
O4B0.3264 (2)0.7168 (2)1.00495 (8)0.0226 (5)
N4B0.4415 (2)0.8728 (2)0.94002 (8)0.0134 (5)
O4C0.3222 (2)0.9098 (2)0.94140 (7)0.0212 (5)
O4D0.5135 (2)0.8680 (2)0.90667 (7)0.0201 (4)
C50.6080 (3)0.7240 (2)0.97549 (9)0.0110 (5)
H5A0.57070.67430.95040.013*
O60.6295 (2)0.66020 (18)1.01752 (6)0.0152 (4)
C70.7669 (3)0.6821 (3)1.03756 (9)0.0145 (6)
H7A0.80470.61191.05250.017*
H7B0.76510.74551.05980.017*
C80.8533 (3)0.7169 (2)0.99663 (9)0.0121 (5)
N8A0.9080 (3)0.6074 (2)0.97344 (8)0.0147 (5)
O8A0.8218 (2)0.55481 (18)0.94906 (7)0.0179 (4)
O8B1.0296 (2)0.5804 (2)0.98126 (8)0.0229 (5)
N8B0.9794 (2)0.7912 (2)1.00924 (8)0.0143 (5)
O8C1.0165 (2)0.7961 (2)1.04939 (7)0.0222 (5)
O8D1.0351 (2)0.83997 (19)0.97747 (7)0.0189 (4)
C1A0.0577 (3)0.6007 (2)0.84852 (9)0.0107 (5)
H1AA0.09090.52870.86300.013*
O2A0.02962 (19)0.69369 (18)0.88088 (6)0.0139 (4)
C3A0.1028 (3)0.7485 (3)0.87306 (9)0.0150 (6)
H3AA0.14820.77490.90160.018*
H3AB0.09160.81510.85240.018*
C4A0.1855 (3)0.6499 (3)0.85155 (9)0.0135 (5)
N4AA0.3029 (3)0.6909 (2)0.82219 (8)0.0185 (5)
O4AA0.3145 (3)0.7956 (2)0.81530 (9)0.0347 (6)
O4BA0.3744 (2)0.6123 (2)0.80674 (7)0.0268 (5)
N4BA0.2533 (2)0.5734 (2)0.88862 (8)0.0156 (5)
O4CA0.1897 (2)0.4850 (2)0.89928 (7)0.0215 (5)
O4DA0.3626 (2)0.6082 (2)0.90666 (8)0.0288 (6)
C5A0.0761 (3)0.5803 (3)0.82240 (9)0.0119 (5)
H5AA0.09990.49660.82030.014*
O6A0.0571 (2)0.63390 (19)0.77838 (6)0.0165 (4)
C7A0.0671 (3)0.7060 (3)0.77668 (9)0.0172 (6)
H7AA0.11110.70660.74620.021*
H7AB0.04570.78630.78590.021*
C8A0.1601 (3)0.6460 (3)0.81062 (9)0.0137 (5)
N8AA0.2380 (3)0.5457 (2)0.78677 (8)0.0155 (5)
O8AA0.1808 (2)0.45007 (18)0.78872 (7)0.0212 (5)
O8BA0.3463 (2)0.5695 (2)0.76567 (8)0.0283 (5)
N8BA0.2691 (3)0.7220 (2)0.83167 (8)0.0169 (5)
O8CA0.2621 (3)0.8282 (2)0.82540 (8)0.0339 (6)
O8DA0.3498 (2)0.6708 (2)0.85547 (7)0.0233 (5)
C1B0.2723 (3)0.7564 (2)0.64048 (9)0.0108 (5)
H1BA0.23520.70340.61640.013*
O2B0.28881 (19)0.69885 (18)0.68363 (6)0.0139 (4)
C3B0.4243 (3)0.7234 (3)0.70494 (9)0.0130 (5)
H3BA0.46010.65550.72190.016*
H3BB0.42010.79010.72560.016*
C4B0.5154 (3)0.7514 (2)0.66449 (9)0.0115 (5)
N4AB0.6410 (2)0.8261 (2)0.67695 (8)0.0127 (5)
O4AB0.6743 (2)0.83470 (19)0.71781 (7)0.0200 (4)
O4BB0.7013 (2)0.86862 (19)0.64514 (7)0.0177 (4)
N4BB0.5718 (3)0.6375 (2)0.64442 (8)0.0138 (5)
O4CB0.6943 (2)0.61284 (19)0.65238 (8)0.0223 (5)
O4DB0.4848 (2)0.57985 (18)0.62275 (7)0.0191 (4)
C5B0.4143 (3)0.8100 (2)0.62874 (9)0.0107 (5)
H5BA0.43880.79180.59730.013*
O6B0.4081 (2)0.93369 (17)0.63671 (7)0.0148 (4)
C7B0.2828 (3)0.9648 (3)0.65868 (9)0.0149 (6)
H7BA0.24781.04040.64780.018*
H7BB0.29930.96890.69160.018*
C8B0.1799 (3)0.8664 (3)0.64578 (9)0.0131 (5)
N8AB0.1021 (2)0.8966 (2)0.60126 (8)0.0134 (5)
O8AB0.1664 (2)0.87608 (19)0.56706 (6)0.0182 (4)
O8BB0.0137 (2)0.9412 (2)0.60270 (7)0.0211 (5)
N8BB0.0700 (2)0.8431 (2)0.68031 (8)0.0152 (5)
O8CB0.0721 (2)0.9036 (2)0.71487 (7)0.0274 (5)
O8DB0.0100 (2)0.7621 (2)0.67099 (7)0.0200 (4)
C1C0.6017 (3)0.6045 (2)0.51792 (9)0.0107 (5)
H1CA0.57590.53270.53420.013*
O2C0.62420 (19)0.70275 (18)0.54808 (6)0.0137 (4)
C3C0.7528 (3)0.7621 (3)0.53860 (9)0.0145 (5)
H3CA0.79760.79340.56640.017*
H3CB0.73630.82600.51700.017*
C4C0.8409 (3)0.6659 (2)0.51821 (9)0.0124 (5)
N4AC0.9547 (2)0.7077 (2)0.48771 (8)0.0164 (5)
O4AC0.9552 (2)0.8113 (2)0.47753 (8)0.0302 (6)
O4BC1.0337 (2)0.6320 (2)0.47494 (7)0.0242 (5)
N4BC0.9139 (2)0.5950 (2)0.55646 (8)0.0144 (5)
O4CC1.0171 (2)0.6390 (2)0.57511 (7)0.0262 (5)
O4DC0.8594 (2)0.5026 (2)0.56688 (7)0.0220 (5)
C5C0.7351 (3)0.5884 (3)0.49087 (8)0.0121 (5)
H5CA0.76470.50590.48930.014*
O6C0.7085 (2)0.63959 (19)0.44642 (6)0.0155 (4)
C7C0.5772 (3)0.7020 (3)0.44469 (10)0.0196 (6)
H7CA0.53150.69680.41450.023*
H7CB0.59050.78430.45270.023*
C8C0.4932 (3)0.6387 (2)0.47998 (9)0.0131 (5)
N8AC0.4264 (3)0.5292 (2)0.45793 (8)0.0176 (5)
O8AC0.3165 (2)0.5413 (2)0.43630 (8)0.0265 (5)
O8BC0.4933 (2)0.4380 (2)0.46263 (7)0.0253 (5)
N8BC0.3716 (3)0.7048 (2)0.49816 (8)0.0193 (5)
O8CC0.3389 (2)0.7968 (2)0.48068 (8)0.0265 (5)
O8DC0.3139 (2)0.6564 (2)0.52969 (7)0.0253 (5)
C1D0.0568 (3)0.7540 (2)0.31042 (8)0.0098 (5)
H1DA0.09600.70020.28700.012*
O2D0.03320 (19)0.69704 (18)0.35343 (6)0.0132 (4)
C3D0.1045 (3)0.7231 (3)0.37243 (9)0.0131 (5)
H3DA0.14380.65570.38880.016*
H3DB0.10240.78980.39320.016*
C4D0.1887 (3)0.7521 (2)0.33080 (9)0.0120 (5)
N4AD0.3152 (2)0.8274 (2)0.34100 (8)0.0139 (5)
O4AD0.3514 (2)0.8391 (2)0.38137 (7)0.0203 (5)
O4BD0.3724 (2)0.86805 (19)0.30805 (7)0.0180 (4)
N4BD0.2443 (2)0.6377 (2)0.31033 (8)0.0144 (5)
O4CD0.3652 (2)0.61142 (19)0.31918 (8)0.0233 (5)
O4DD0.1581 (2)0.58172 (18)0.28765 (7)0.0178 (4)
C5D0.0821 (3)0.8096 (2)0.29646 (9)0.0101 (5)
H5DA0.10250.79250.26460.012*
O6D0.0757 (2)0.93289 (17)0.30534 (7)0.0148 (4)
C7D0.0464 (3)0.9621 (3)0.32940 (10)0.0159 (6)
H7DA0.08331.03820.31970.019*
H7DB0.02590.96400.36220.019*
C8D0.1502 (3)0.8632 (2)0.31665 (9)0.0124 (5)
N8AD0.2299 (2)0.8937 (2)0.27259 (7)0.0125 (5)
O8AD0.3439 (2)0.94119 (19)0.27512 (7)0.0211 (5)
O8BD0.1696 (2)0.87099 (19)0.23780 (7)0.0190 (4)
N8BD0.2577 (2)0.8384 (2)0.35187 (8)0.0157 (5)
O8CD0.2543 (2)0.8987 (2)0.38644 (7)0.0254 (5)
O8DD0.3380 (2)0.7579 (2)0.34257 (7)0.0209 (5)
C1E0.2773 (3)0.6021 (2)0.18613 (9)0.0099 (5)
H1EA0.25170.53430.20480.012*
O2E0.30123 (19)0.70436 (17)0.21379 (6)0.0129 (4)
C3E0.4285 (3)0.7615 (3)0.20131 (9)0.0144 (5)
H3EA0.47360.80110.22740.017*
H3EB0.41070.81820.17690.017*
C4E0.5175 (3)0.6586 (2)0.18516 (9)0.0126 (5)
N4AE0.6325 (2)0.6932 (2)0.15387 (8)0.0169 (5)
O4AE0.6389 (2)0.7946 (2)0.14153 (8)0.0295 (5)
O4BE0.7080 (2)0.6123 (2)0.14278 (8)0.0278 (5)
N4BE0.5883 (2)0.5956 (2)0.22558 (8)0.0153 (5)
O4CE0.6923 (3)0.6420 (2)0.24301 (8)0.0334 (6)
O4DE0.5331 (2)0.5069 (2)0.23893 (7)0.0234 (5)
C5E0.4120 (3)0.5772 (2)0.16058 (8)0.0106 (5)
H5EA0.43990.49410.16140.013*
O6E0.3890 (2)0.62222 (18)0.11537 (6)0.0143 (4)
C7E0.2465 (3)0.5975 (3)0.10231 (9)0.0183 (6)
H7EA0.23500.51590.09290.022*
H7EB0.21360.64830.07740.022*
C8E0.1678 (3)0.6224 (2)0.14578 (9)0.0128 (5)
N8AE0.0419 (3)0.5420 (2)0.14822 (8)0.0188 (5)
O8AE0.0079 (2)0.5065 (2)0.18562 (7)0.0265 (5)
O8BE0.0189 (2)0.5210 (2)0.11127 (7)0.0222 (5)
N8BE0.1099 (3)0.7468 (2)0.14659 (8)0.0172 (5)
O8CE0.0009 (2)0.7625 (2)0.16355 (8)0.0258 (5)
O8DE0.1855 (2)0.82098 (19)0.13063 (7)0.0215 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0124 (12)0.0104 (13)0.0103 (12)0.0021 (10)0.0005 (10)0.0009 (10)
O20.0132 (9)0.0092 (10)0.0210 (10)0.0011 (8)0.0013 (8)0.0017 (8)
C30.0150 (13)0.0157 (15)0.0160 (13)0.0022 (11)0.0007 (11)0.0048 (11)
C40.0115 (12)0.0102 (13)0.0130 (12)0.0005 (10)0.0049 (10)0.0005 (10)
N4A0.0151 (12)0.0180 (13)0.0184 (12)0.0060 (10)0.0044 (10)0.0041 (10)
O4A0.0300 (12)0.0341 (14)0.0220 (11)0.0042 (10)0.0128 (10)0.0063 (10)
O4B0.0174 (10)0.0196 (12)0.0311 (12)0.0023 (9)0.0064 (9)0.0036 (9)
N4B0.0146 (11)0.0090 (11)0.0163 (11)0.0009 (9)0.0030 (9)0.0001 (9)
O4C0.0139 (10)0.0200 (11)0.0292 (11)0.0022 (9)0.0037 (9)0.0017 (9)
O4D0.0235 (11)0.0206 (11)0.0164 (10)0.0006 (9)0.0018 (9)0.0039 (8)
C50.0119 (12)0.0109 (13)0.0101 (12)0.0003 (10)0.0015 (10)0.0017 (10)
O60.0122 (9)0.0182 (11)0.0153 (9)0.0007 (8)0.0001 (8)0.0066 (8)
C70.0122 (13)0.0206 (15)0.0108 (12)0.0005 (11)0.0005 (10)0.0031 (11)
C80.0121 (12)0.0126 (13)0.0115 (12)0.0016 (11)0.0006 (10)0.0001 (10)
N8A0.0168 (12)0.0101 (12)0.0174 (11)0.0018 (9)0.0034 (10)0.0006 (9)
O8A0.0205 (10)0.0151 (10)0.0180 (10)0.0013 (8)0.0004 (8)0.0053 (8)
O8B0.0156 (11)0.0205 (12)0.0325 (12)0.0072 (9)0.0003 (9)0.0024 (9)
N8B0.0099 (11)0.0156 (12)0.0173 (12)0.0021 (9)0.0017 (9)0.0037 (9)
O8C0.0232 (11)0.0261 (12)0.0165 (10)0.0036 (9)0.0076 (8)0.0015 (9)
O8D0.0145 (10)0.0200 (11)0.0226 (10)0.0030 (8)0.0052 (8)0.0003 (9)
C1A0.0130 (13)0.0085 (13)0.0105 (12)0.0015 (10)0.0003 (10)0.0014 (10)
O2A0.0130 (9)0.0156 (10)0.0132 (9)0.0014 (8)0.0013 (7)0.0055 (8)
C3A0.0143 (13)0.0150 (14)0.0162 (13)0.0029 (11)0.0043 (11)0.0035 (11)
C4A0.0142 (13)0.0180 (14)0.0082 (12)0.0001 (11)0.0001 (10)0.0001 (10)
N4AA0.0154 (12)0.0273 (15)0.0129 (11)0.0040 (11)0.0020 (9)0.0004 (10)
O4AA0.0376 (14)0.0299 (14)0.0377 (13)0.0114 (12)0.0151 (11)0.0059 (11)
O4BA0.0191 (11)0.0402 (15)0.0215 (11)0.0029 (10)0.0068 (9)0.0036 (10)
N4BA0.0142 (12)0.0193 (14)0.0131 (11)0.0024 (10)0.0006 (9)0.0015 (10)
O4CA0.0242 (11)0.0193 (12)0.0207 (10)0.0004 (9)0.0021 (9)0.0044 (9)
O4DA0.0204 (12)0.0422 (16)0.0227 (11)0.0089 (10)0.0113 (9)0.0049 (10)
C5A0.0130 (13)0.0127 (13)0.0100 (12)0.0008 (11)0.0006 (10)0.0009 (10)
O6A0.0148 (10)0.0261 (12)0.0086 (9)0.0009 (8)0.0015 (7)0.0009 (8)
C7A0.0179 (14)0.0193 (15)0.0144 (13)0.0012 (12)0.0004 (11)0.0059 (11)
C8A0.0148 (13)0.0126 (14)0.0135 (12)0.0015 (11)0.0007 (11)0.0004 (10)
N8AA0.0166 (12)0.0191 (13)0.0107 (10)0.0013 (10)0.0010 (9)0.0007 (9)
O8AA0.0315 (12)0.0138 (11)0.0178 (10)0.0014 (9)0.0044 (9)0.0019 (8)
O8BA0.0181 (11)0.0335 (14)0.0322 (12)0.0037 (10)0.0102 (10)0.0102 (11)
N8BA0.0169 (12)0.0194 (13)0.0141 (11)0.0066 (10)0.0008 (10)0.0031 (10)
O8CA0.0473 (16)0.0167 (12)0.0387 (14)0.0134 (11)0.0120 (12)0.0033 (10)
O8DA0.0159 (10)0.0291 (13)0.0254 (11)0.0002 (9)0.0071 (9)0.0046 (9)
C1B0.0115 (12)0.0106 (13)0.0102 (11)0.0004 (10)0.0003 (10)0.0004 (10)
O2B0.0113 (9)0.0175 (11)0.0129 (9)0.0019 (8)0.0007 (7)0.0066 (8)
C3B0.0111 (12)0.0179 (14)0.0098 (12)0.0027 (11)0.0019 (10)0.0025 (10)
C4B0.0100 (12)0.0122 (13)0.0121 (12)0.0003 (10)0.0014 (10)0.0015 (10)
N4AB0.0107 (11)0.0089 (11)0.0184 (11)0.0009 (9)0.0002 (9)0.0015 (9)
O4AB0.0211 (11)0.0242 (12)0.0140 (10)0.0027 (9)0.0055 (8)0.0022 (9)
O4BB0.0140 (10)0.0180 (11)0.0215 (10)0.0021 (8)0.0037 (8)0.0023 (8)
N4BB0.0144 (12)0.0114 (12)0.0157 (11)0.0013 (9)0.0019 (9)0.0020 (9)
O4CB0.0147 (10)0.0187 (12)0.0330 (12)0.0058 (8)0.0039 (9)0.0012 (9)
O4DB0.0208 (11)0.0136 (11)0.0229 (10)0.0025 (9)0.0002 (9)0.0035 (8)
C5B0.0099 (12)0.0109 (13)0.0113 (12)0.0012 (10)0.0005 (10)0.0019 (10)
O6B0.0130 (9)0.0087 (10)0.0229 (10)0.0018 (7)0.0017 (8)0.0005 (8)
C7B0.0114 (13)0.0161 (14)0.0169 (13)0.0012 (11)0.0023 (11)0.0039 (11)
C8B0.0120 (13)0.0158 (14)0.0113 (12)0.0007 (11)0.0009 (10)0.0005 (10)
N8AB0.0141 (11)0.0089 (11)0.0168 (11)0.0014 (9)0.0032 (9)0.0023 (9)
O8AB0.0234 (11)0.0181 (11)0.0132 (9)0.0003 (9)0.0029 (8)0.0044 (8)
O8BB0.0144 (10)0.0241 (12)0.0244 (11)0.0042 (9)0.0040 (9)0.0053 (9)
N8BB0.0156 (12)0.0166 (13)0.0136 (11)0.0053 (10)0.0040 (9)0.0026 (9)
O8CB0.0351 (13)0.0291 (13)0.0189 (11)0.0017 (11)0.0133 (10)0.0064 (9)
O8DB0.0146 (10)0.0231 (12)0.0223 (10)0.0009 (9)0.0018 (8)0.0055 (9)
C1C0.0128 (13)0.0105 (13)0.0090 (11)0.0004 (10)0.0005 (10)0.0026 (10)
O2C0.0133 (9)0.0137 (10)0.0141 (9)0.0006 (8)0.0017 (7)0.0049 (8)
C3C0.0117 (12)0.0128 (13)0.0189 (13)0.0003 (11)0.0002 (11)0.0014 (11)
C4C0.0126 (13)0.0124 (14)0.0123 (12)0.0002 (10)0.0015 (10)0.0004 (10)
N4AC0.0145 (12)0.0209 (14)0.0138 (11)0.0049 (10)0.0004 (9)0.0001 (10)
O4AC0.0286 (13)0.0265 (14)0.0362 (13)0.0061 (10)0.0092 (11)0.0100 (11)
O4BC0.0190 (11)0.0339 (14)0.0203 (11)0.0008 (10)0.0072 (9)0.0021 (10)
N4BC0.0151 (12)0.0152 (13)0.0129 (11)0.0025 (10)0.0007 (9)0.0012 (9)
O4CC0.0221 (11)0.0347 (14)0.0208 (11)0.0098 (10)0.0119 (9)0.0048 (10)
O4DC0.0248 (11)0.0191 (12)0.0217 (10)0.0001 (9)0.0042 (9)0.0079 (9)
C5C0.0141 (13)0.0132 (13)0.0090 (11)0.0002 (11)0.0009 (10)0.0000 (10)
O6C0.0120 (9)0.0227 (11)0.0119 (9)0.0012 (8)0.0001 (7)0.0013 (8)
C7C0.0169 (14)0.0259 (17)0.0158 (13)0.0011 (13)0.0008 (11)0.0052 (12)
C8C0.0149 (13)0.0115 (13)0.0127 (12)0.0018 (11)0.0021 (10)0.0038 (10)
N8AC0.0193 (13)0.0172 (13)0.0159 (11)0.0003 (10)0.0016 (10)0.0016 (10)
O8AC0.0206 (11)0.0273 (13)0.0304 (12)0.0028 (10)0.0110 (10)0.0047 (10)
O8BC0.0268 (12)0.0179 (12)0.0305 (12)0.0024 (9)0.0075 (10)0.0043 (9)
N8BC0.0158 (12)0.0240 (14)0.0178 (12)0.0040 (11)0.0033 (10)0.0040 (11)
O8CC0.0282 (12)0.0217 (12)0.0292 (12)0.0111 (10)0.0041 (10)0.0015 (10)
O8DC0.0198 (11)0.0347 (14)0.0219 (11)0.0009 (10)0.0063 (9)0.0033 (10)
C1D0.0101 (12)0.0084 (12)0.0110 (12)0.0006 (10)0.0011 (10)0.0012 (10)
O2D0.0105 (9)0.0169 (10)0.0119 (9)0.0024 (8)0.0021 (7)0.0049 (8)
C3D0.0097 (12)0.0197 (15)0.0098 (12)0.0006 (10)0.0009 (10)0.0023 (10)
C4D0.0112 (12)0.0125 (13)0.0123 (12)0.0001 (10)0.0013 (10)0.0022 (10)
N4AD0.0125 (11)0.0093 (11)0.0197 (12)0.0020 (9)0.0007 (9)0.0000 (9)
O4AD0.0194 (10)0.0251 (12)0.0158 (10)0.0057 (9)0.0062 (8)0.0007 (9)
O4BD0.0141 (10)0.0202 (11)0.0202 (10)0.0030 (8)0.0041 (8)0.0028 (8)
N4BD0.0138 (12)0.0133 (12)0.0164 (11)0.0020 (9)0.0018 (9)0.0019 (9)
O4CD0.0166 (11)0.0189 (12)0.0343 (12)0.0073 (9)0.0011 (9)0.0020 (9)
O4DD0.0217 (11)0.0144 (11)0.0172 (10)0.0023 (9)0.0007 (8)0.0029 (8)
C5D0.0109 (12)0.0092 (13)0.0100 (11)0.0011 (10)0.0005 (10)0.0019 (9)
O6D0.0120 (9)0.0095 (10)0.0231 (10)0.0007 (8)0.0014 (8)0.0012 (8)
C7D0.0141 (13)0.0121 (14)0.0213 (14)0.0003 (11)0.0000 (11)0.0051 (11)
C8D0.0122 (13)0.0150 (14)0.0100 (12)0.0001 (10)0.0009 (10)0.0004 (10)
N8AD0.0150 (12)0.0092 (11)0.0131 (11)0.0030 (9)0.0015 (9)0.0034 (9)
O8AD0.0168 (10)0.0210 (12)0.0253 (11)0.0051 (9)0.0023 (9)0.0048 (9)
O8BD0.0253 (11)0.0176 (11)0.0141 (9)0.0029 (9)0.0017 (8)0.0047 (8)
N8BD0.0143 (12)0.0190 (13)0.0142 (11)0.0042 (10)0.0028 (9)0.0044 (10)
O8CD0.0294 (12)0.0296 (13)0.0177 (10)0.0035 (10)0.0077 (9)0.0053 (9)
O8DD0.0150 (10)0.0214 (12)0.0264 (11)0.0000 (9)0.0038 (9)0.0059 (9)
C1E0.0121 (12)0.0078 (12)0.0097 (11)0.0011 (10)0.0016 (10)0.0007 (10)
O2E0.0149 (9)0.0114 (10)0.0124 (9)0.0022 (8)0.0020 (7)0.0041 (7)
C3E0.0154 (13)0.0125 (14)0.0152 (13)0.0016 (11)0.0021 (11)0.0006 (11)
C4E0.0143 (13)0.0131 (14)0.0105 (12)0.0021 (10)0.0015 (10)0.0003 (10)
N4AE0.0137 (11)0.0224 (14)0.0147 (11)0.0044 (10)0.0029 (9)0.0016 (10)
O4AE0.0298 (12)0.0273 (13)0.0323 (12)0.0068 (10)0.0105 (10)0.0105 (10)
O4BE0.0197 (11)0.0329 (14)0.0316 (12)0.0031 (10)0.0100 (10)0.0007 (10)
N4BE0.0165 (12)0.0156 (13)0.0136 (11)0.0009 (10)0.0017 (9)0.0003 (9)
O4CE0.0297 (13)0.0364 (15)0.0321 (13)0.0127 (11)0.0196 (11)0.0095 (11)
O4DE0.0267 (12)0.0227 (12)0.0204 (10)0.0037 (10)0.0052 (9)0.0117 (9)
C5E0.0110 (12)0.0120 (13)0.0088 (11)0.0009 (10)0.0010 (10)0.0015 (10)
O6E0.0152 (10)0.0192 (11)0.0085 (8)0.0011 (8)0.0009 (7)0.0018 (7)
C7E0.0194 (15)0.0215 (16)0.0137 (13)0.0021 (12)0.0021 (11)0.0001 (11)
C8E0.0122 (13)0.0119 (14)0.0140 (12)0.0024 (10)0.0025 (10)0.0023 (10)
N8AE0.0158 (12)0.0167 (13)0.0238 (13)0.0008 (10)0.0017 (10)0.0002 (10)
O8AE0.0249 (12)0.0307 (13)0.0240 (11)0.0060 (10)0.0026 (9)0.0033 (10)
O8BE0.0190 (11)0.0268 (12)0.0200 (10)0.0020 (9)0.0077 (9)0.0064 (9)
N8BE0.0223 (13)0.0165 (13)0.0125 (11)0.0018 (10)0.0042 (10)0.0022 (9)
O8CE0.0159 (10)0.0277 (13)0.0338 (12)0.0040 (9)0.0021 (9)0.0109 (10)
O8DE0.0316 (12)0.0168 (11)0.0162 (10)0.0022 (9)0.0005 (9)0.0023 (8)
Geometric parameters (Å, º) top
C1—O21.429 (3)C1C—O2C1.432 (3)
C1—C51.534 (4)C1C—C8C1.536 (4)
C1—C81.537 (4)C1C—C5C1.542 (3)
C1—H1A0.9800C1C—H1CA0.9800
O2—C31.431 (3)O2C—C3C1.441 (3)
C3—C41.525 (4)C3C—C4C1.519 (4)
C3—H3A0.9700C3C—H3CA0.9700
C3—H3B0.9700C3C—H3CB0.9700
C4—N4A1.511 (3)C4C—N4AC1.515 (3)
C4—N4B1.520 (3)C4C—N4BC1.521 (4)
C4—C51.538 (4)C4C—C5C1.538 (4)
N4A—O4A1.210 (3)N4AC—O4AC1.213 (3)
N4A—O4B1.226 (3)N4AC—O4BC1.214 (3)
N4B—O4C1.219 (3)N4BC—O4CC1.215 (3)
N4B—O4D1.221 (3)N4BC—O4DC1.216 (3)
C5—O61.433 (3)C5C—O6C1.436 (3)
C5—H5A0.9800C5C—H5CA0.9800
O6—C71.438 (3)O6C—C7C1.442 (3)
C7—C81.537 (4)C7C—C8C1.517 (4)
C7—H7A0.9700C7C—H7CA0.9700
C7—H7B0.9700C7C—H7CB0.9700
C8—N8B1.505 (4)C8C—N8BC1.502 (4)
C8—N8A1.519 (3)C8C—N8AC1.527 (4)
N8A—O8B1.216 (3)N8AC—O8AC1.211 (3)
N8A—O8A1.222 (3)N8AC—O8BC1.222 (3)
N8B—O8C1.212 (3)N8BC—O8CC1.198 (3)
N8B—O8D1.224 (3)N8BC—O8DC1.225 (3)
C1A—O2A1.435 (3)C1D—O2D1.423 (3)
C1A—C8A1.535 (4)C1D—C8D1.543 (4)
C1A—C5A1.538 (4)C1D—C5D1.544 (4)
C1A—H1AA0.9800C1D—H1DA0.9800
O2A—C3A1.440 (3)O2D—C3D1.439 (3)
C3A—C4A1.523 (4)C3D—C4D1.525 (3)
C3A—H3AA0.9700C3D—H3DA0.9700
C3A—H3AB0.9700C3D—H3DB0.9700
C4A—N4BA1.512 (4)C4D—N4AD1.501 (4)
C4A—N4AA1.518 (4)C4D—N4BD1.535 (4)
C4A—C5A1.539 (4)C4D—C5D1.544 (4)
N4AA—O4AA1.211 (4)N4AD—O4BD1.220 (3)
N4AA—O4BA1.222 (3)N4AD—O4AD1.223 (3)
N4BA—O4DA1.217 (3)N4BD—O4CD1.213 (3)
N4BA—O4CA1.221 (3)N4BD—O4DD1.215 (3)
C5A—O6A1.428 (3)C5D—O6D1.424 (3)
C5A—H5AA0.9800C5D—H5DA0.9800
O6A—C7A1.442 (3)O6D—C7D1.430 (3)
C7A—C8A1.523 (4)C7D—C8D1.534 (4)
C7A—H7AA0.9700C7D—H7DA0.9700
C7A—H7AB0.9700C7D—H7DB0.9700
C8A—N8BA1.506 (4)C8D—N8AD1.508 (3)
C8A—N8AA1.514 (4)C8D—N8BD1.514 (3)
N8AA—O8BA1.213 (3)N8AD—O8BD1.219 (3)
N8AA—O8AA1.216 (3)N8AD—O8AD1.222 (3)
N8BA—O8DA1.211 (3)N8BD—O8DD1.217 (3)
N8BA—O8CA1.221 (4)N8BD—O8CD1.220 (3)
C1B—O2B1.423 (3)C1E—O2E1.427 (3)
C1B—C8B1.542 (4)C1E—C5E1.545 (3)
C1B—C5B1.542 (4)C1E—C8E1.560 (4)
C1B—H1BA0.9800C1E—H1EA0.9800
O2B—C3B1.441 (3)O2E—C3E1.442 (3)
C3B—C4B1.534 (4)C3E—C4E1.533 (4)
C3B—H3BA0.9700C3E—H3EA0.9700
C3B—H3BB0.9700C3E—H3EB0.9700
C4B—N4AB1.502 (3)C4E—N4AE1.514 (3)
C4B—N4BB1.528 (4)C4E—N4BE1.515 (4)
C4B—C5B1.543 (4)C4E—C5E1.525 (4)
N4AB—O4BB1.217 (3)N4AE—O4AE1.209 (4)
N4AB—O4AB1.227 (3)N4AE—O4BE1.221 (3)
N4BB—O4DB1.215 (3)N4BE—O4DE1.209 (3)
N4BB—O4CB1.218 (3)N4BE—O4CE1.219 (3)
C5B—O6B1.424 (3)C5E—O6E1.425 (3)
C5B—H5BA0.9800C5E—H5EA0.9800
O6B—C7B1.430 (3)O6E—C7E1.429 (3)
C7B—C8B1.526 (4)C7E—C8E1.532 (4)
C7B—H7BA0.9700C7E—H7EA0.9700
C7B—H7BB0.9700C7E—H7EB0.9700
C8B—N8AB1.510 (3)C8E—N8AE1.516 (4)
C8B—N8BB1.513 (3)C8E—N8BE1.517 (4)
N8AB—O8AB1.220 (3)N8AE—O8AE1.223 (3)
N8AB—O8BB1.221 (3)N8AE—O8BE1.228 (3)
N8BB—O8DB1.219 (3)N8BE—O8CE1.204 (3)
N8BB—O8CB1.221 (3)N8BE—O8DE1.217 (3)
O2—C1—C5107.7 (2)O2C—C1C—C8C109.0 (2)
O2—C1—C8108.8 (2)O2C—C1C—C5C107.6 (2)
C5—C1—C8103.0 (2)C8C—C1C—C5C102.0 (2)
O2—C1—H1A112.3O2C—C1C—H1CA112.5
C5—C1—H1A112.3C8C—C1C—H1CA112.5
C8—C1—H1A112.3C5C—C1C—H1CA112.5
C1—O2—C3110.7 (2)C1C—O2C—C3C110.60 (19)
O2—C3—C4104.1 (2)O2C—C3C—C4C103.5 (2)
O2—C3—H3A110.9O2C—C3C—H3CA111.1
C4—C3—H3A110.9C4C—C3C—H3CA111.1
O2—C3—H3B110.9O2C—C3C—H3CB111.1
C4—C3—H3B110.9C4C—C3C—H3CB111.1
H3A—C3—H3B108.9H3CA—C3C—H3CB109.0
N4A—C4—N4B106.4 (2)N4AC—C4C—C3C115.6 (2)
N4A—C4—C3114.4 (2)N4AC—C4C—N4BC106.3 (2)
N4B—C4—C3109.9 (2)C3C—C4C—N4BC109.7 (2)
N4A—C4—C5111.8 (2)N4AC—C4C—C5C110.3 (2)
N4B—C4—C5110.6 (2)C3C—C4C—C5C104.5 (2)
C3—C4—C5103.8 (2)N4BC—C4C—C5C110.5 (2)
O4A—N4A—O4B127.0 (2)O4AC—N4AC—O4BC127.0 (3)
O4A—N4A—C4117.6 (2)O4AC—N4AC—C4C117.3 (2)
O4B—N4A—C4115.4 (2)O4BC—N4AC—C4C115.7 (2)
O4C—N4B—O4D127.2 (2)O4CC—N4BC—O4DC126.3 (3)
O4C—N4B—C4118.3 (2)O4CC—N4BC—C4C116.8 (2)
O4D—N4B—C4114.4 (2)O4DC—N4BC—C4C116.9 (2)
O6—C5—C1107.5 (2)O6C—C5C—C4C109.0 (2)
O6—C5—C4108.5 (2)O6C—C5C—C1C107.4 (2)
C1—C5—C4102.5 (2)C4C—C5C—C1C102.0 (2)
O6—C5—H5A112.6O6C—C5C—H5CA112.6
C1—C5—H5A112.6C4C—C5C—H5CA112.6
C4—C5—H5A112.6C1C—C5C—H5CA112.6
C5—O6—C7110.8 (2)C5C—O6C—C7C110.45 (19)
O6—C7—C8104.0 (2)O6C—C7C—C8C103.4 (2)
O6—C7—H7A111.0O6C—C7C—H7CA111.1
C8—C7—H7A111.0C8C—C7C—H7CA111.1
O6—C7—H7B111.0O6C—C7C—H7CB111.1
C8—C7—H7B111.0C8C—C7C—H7CB111.1
H7A—C7—H7B109.0H7CA—C7C—H7CB109.1
N8B—C8—N8A106.2 (2)N8BC—C8C—C7C116.6 (2)
N8B—C8—C7114.0 (2)N8BC—C8C—N8AC103.8 (2)
N8A—C8—C7110.2 (2)C7C—C8C—N8AC108.8 (2)
N8B—C8—C1112.3 (2)N8BC—C8C—C1C112.4 (2)
N8A—C8—C1110.7 (2)C7C—C8C—C1C104.4 (2)
C7—C8—C1103.5 (2)N8AC—C8C—C1C110.9 (2)
O8B—N8A—O8A127.1 (2)O8AC—N8AC—O8BC126.4 (3)
O8B—N8A—C8117.9 (2)O8AC—N8AC—C8C117.8 (2)
O8A—N8A—C8115.0 (2)O8BC—N8AC—C8C115.7 (2)
O8C—N8B—O8D126.6 (2)O8CC—N8BC—O8DC126.4 (3)
O8C—N8B—C8117.4 (2)O8CC—N8BC—C8C118.4 (2)
O8D—N8B—C8116.0 (2)O8DC—N8BC—C8C115.2 (3)
O2A—C1A—C8A109.0 (2)O2D—C1D—C8D109.3 (2)
O2A—C1A—C5A107.6 (2)O2D—C1D—C5D108.3 (2)
C8A—C1A—C5A102.2 (2)C8D—C1D—C5D102.3 (2)
O2A—C1A—H1AA112.5O2D—C1D—H1DA112.1
C8A—C1A—H1AA112.5C8D—C1D—H1DA112.1
C5A—C1A—H1AA112.5C5D—C1D—H1DA112.1
C1A—O2A—C3A110.71 (19)C1D—O2D—C3D110.78 (19)
O2A—C3A—C4A103.1 (2)O2D—C3D—C4D104.1 (2)
O2A—C3A—H3AA111.1O2D—C3D—H3DA110.9
C4A—C3A—H3AA111.1C4D—C3D—H3DA110.9
O2A—C3A—H3AB111.1O2D—C3D—H3DB110.9
C4A—C3A—H3AB111.1C4D—C3D—H3DB110.9
H3AA—C3A—H3AB109.1H3DA—C3D—H3DB109.0
N4BA—C4A—N4AA106.1 (2)N4AD—C4D—C3D114.5 (2)
N4BA—C4A—C3A109.9 (2)N4AD—C4D—N4BD105.5 (2)
N4AA—C4A—C3A114.8 (2)C3D—C4D—N4BD109.5 (2)
N4BA—C4A—C5A111.3 (2)N4AD—C4D—C5D113.1 (2)
N4AA—C4A—C5A110.3 (2)C3D—C4D—C5D104.6 (2)
C3A—C4A—C5A104.6 (2)N4BD—C4D—C5D109.5 (2)
O4AA—N4AA—O4BA126.7 (3)O4BD—N4AD—O4AD127.1 (2)
O4AA—N4AA—C4A118.1 (3)O4BD—N4AD—C4D116.4 (2)
O4BA—N4AA—C4A115.2 (3)O4AD—N4AD—C4D116.4 (2)
O4DA—N4BA—O4CA125.8 (3)O4CD—N4BD—O4DD127.4 (3)
O4DA—N4BA—C4A117.2 (2)O4CD—N4BD—C4D118.0 (2)
O4CA—N4BA—C4A116.8 (2)O4DD—N4BD—C4D114.6 (2)
O6A—C5A—C1A107.9 (2)O6D—C5D—C1D108.0 (2)
O6A—C5A—C4A109.7 (2)O6D—C5D—C4D109.2 (2)
C1A—C5A—C4A102.1 (2)C1D—C5D—C4D102.0 (2)
O6A—C5A—H5AA112.2O6D—C5D—H5DA112.4
C1A—C5A—H5AA112.2C1D—C5D—H5DA112.4
C4A—C5A—H5AA112.2C4D—C5D—H5DA112.4
C5A—O6A—C7A110.15 (19)C5D—O6D—C7D111.1 (2)
O6A—C7A—C8A103.3 (2)O6D—C7D—C8D104.2 (2)
O6A—C7A—H7AA111.1O6D—C7D—H7DA110.9
C8A—C7A—H7AA111.1C8D—C7D—H7DA110.9
O6A—C7A—H7AB111.1O6D—C7D—H7DB110.9
C8A—C7A—H7AB111.1C8D—C7D—H7DB110.9
H7AA—C7A—H7AB109.1H7DA—C7D—H7DB108.9
N8BA—C8A—N8AA106.4 (2)N8AD—C8D—N8BD106.9 (2)
N8BA—C8A—C7A116.5 (2)N8AD—C8D—C7D109.7 (2)
N8AA—C8A—C7A109.0 (2)N8BD—C8D—C7D115.0 (2)
N8BA—C8A—C1A109.2 (2)N8AD—C8D—C1D110.9 (2)
N8AA—C8A—C1A111.5 (2)N8BD—C8D—C1D110.3 (2)
C7A—C8A—C1A104.3 (2)C7D—C8D—C1D104.1 (2)
O8BA—N8AA—O8AA126.5 (3)O8BD—N8AD—O8AD126.9 (2)
O8BA—N8AA—C8A117.4 (2)O8BD—N8AD—C8D115.1 (2)
O8AA—N8AA—C8A116.0 (2)O8AD—N8AD—C8D118.0 (2)
O8DA—N8BA—O8CA126.9 (3)O8DD—N8BD—O8CD126.8 (2)
O8DA—N8BA—C8A115.6 (2)O8DD—N8BD—C8D115.4 (2)
O8CA—N8BA—C8A117.4 (2)O8CD—N8BD—C8D117.7 (2)
O2B—C1B—C8B108.9 (2)O2E—C1E—C5E107.8 (2)
O2B—C1B—C5B108.3 (2)O2E—C1E—C8E113.2 (2)
C8B—C1B—C5B102.6 (2)C5E—C1E—C8E102.0 (2)
O2B—C1B—H1BA112.2O2E—C1E—H1EA111.1
C8B—C1B—H1BA112.2C5E—C1E—H1EA111.1
C5B—C1B—H1BA112.2C8E—C1E—H1EA111.1
C1B—O2B—C3B110.93 (19)C1E—O2E—C3E109.79 (19)
O2B—C3B—C4B103.8 (2)O2E—C3E—C4E102.9 (2)
O2B—C3B—H3BA111.0O2E—C3E—H3EA111.2
C4B—C3B—H3BA111.0C4E—C3E—H3EA111.2
O2B—C3B—H3BB111.0O2E—C3E—H3EB111.2
C4B—C3B—H3BB111.0C4E—C3E—H3EB111.2
H3BA—C3B—H3BB109.0H3EA—C3E—H3EB109.1
N4AB—C4B—N4BB106.1 (2)N4AE—C4E—N4BE106.4 (2)
N4AB—C4B—C3B114.0 (2)N4AE—C4E—C5E110.9 (2)
N4BB—C4B—C3B110.1 (2)N4BE—C4E—C5E110.3 (2)
N4AB—C4B—C5B113.1 (2)N4AE—C4E—C3E114.7 (2)
N4BB—C4B—C5B109.0 (2)N4BE—C4E—C3E110.8 (2)
C3B—C4B—C5B104.5 (2)C5E—C4E—C3E103.9 (2)
O4BB—N4AB—O4AB126.9 (2)O4AE—N4AE—O4BE126.7 (2)
O4BB—N4AB—C4B116.1 (2)O4AE—N4AE—C4E118.4 (2)
O4AB—N4AB—C4B116.9 (2)O4BE—N4AE—C4E114.9 (2)
O4DB—N4BB—O4CB127.4 (3)O4DE—N4BE—O4CE125.9 (3)
O4DB—N4BB—C4B114.2 (2)O4DE—N4BE—C4E117.2 (2)
O4CB—N4BB—C4B118.3 (2)O4CE—N4BE—C4E116.8 (2)
O6B—C5B—C1B108.0 (2)O6E—C5E—C4E107.0 (2)
O6B—C5B—C4B110.1 (2)O6E—C5E—C1E106.6 (2)
C1B—C5B—C4B102.2 (2)C4E—C5E—C1E102.2 (2)
O6B—C5B—H5BA112.0O6E—C5E—H5EA113.4
C1B—C5B—H5BA112.0C4E—C5E—H5EA113.4
C4B—C5B—H5BA112.0C1E—C5E—H5EA113.4
C5B—O6B—C7B111.0 (2)C5E—O6E—C7E106.46 (19)
O6B—C7B—C8B104.7 (2)O6E—C7E—C8E103.9 (2)
O6B—C7B—H7BA110.8O6E—C7E—H7EA111.0
C8B—C7B—H7BA110.8C8E—C7E—H7EA111.0
O6B—C7B—H7BB110.8O6E—C7E—H7EB111.0
C8B—C7B—H7BB110.8C8E—C7E—H7EB111.0
H7BA—C7B—H7BB108.9H7EA—C7E—H7EB109.0
N8AB—C8B—N8BB106.5 (2)N8AE—C8E—N8BE105.5 (2)
N8AB—C8B—C7B109.6 (2)N8AE—C8E—C7E110.4 (2)
N8BB—C8B—C7B115.1 (2)N8BE—C8E—C7E112.2 (2)
N8AB—C8B—C1B111.1 (2)N8AE—C8E—C1E112.6 (2)
N8BB—C8B—C1B110.1 (2)N8BE—C8E—C1E111.1 (2)
C7B—C8B—C1B104.5 (2)C7E—C8E—C1E105.2 (2)
O8AB—N8AB—O8BB126.8 (2)O8AE—N8AE—O8BE126.0 (3)
O8AB—N8AB—C8B114.6 (2)O8AE—N8AE—C8E119.0 (2)
O8BB—N8AB—C8B118.5 (2)O8BE—N8AE—C8E115.0 (2)
O8DB—N8BB—O8CB126.6 (2)O8CE—N8BE—O8DE127.2 (3)
O8DB—N8BB—C8B115.5 (2)O8CE—N8BE—C8E118.3 (2)
O8CB—N8BB—C8B117.8 (2)O8DE—N8BE—C8E114.4 (2)

Experimental details

Crystal data
Chemical formulaC6H6N4O10
Mr294.15
Crystal system, space groupMonoclinic, P21
Temperature (K)93
a, b, c (Å)9.5746 (9), 11.347 (1), 29.241 (3)
β (°) 92.546 (2)
V3)3173.8 (5)
Z12
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.45 × 0.22 × 0.12
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
diffractometer
Absorption correctionIntegration
(SHELXTL; Bruker 2001)
Tmin, Tmax0.922, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
25608, 13028, 10983
Rint0.029
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.130, 0.89
No. of reflections13028
No. of parameters1081
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.52, 0.26

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SnB (Weeks & Miller, 1999), SHELXTL (Sheldrick, 1997), SHELXTL (Bruker, 2001) and MidasPlus (Ferrin et al., 1988; Huang et al., 1991), SHELXTL (Bruker, 2001) and XPREP (Bruker, 2001).

 

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