Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802014101/cv6131sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802014101/cv6131Isup2.hkl |
CCDC reference: 197479
Crystals of (I) were grown from 2-butanone octane. The sample was provided by Kurt Baum of Fluorochem, Inc.
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).
C6H6N4O10 | F(000) = 1800 |
Mr = 294.15 | Dx = 1.847 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.5746 (9) Å | Cell parameters from 7125 reflections |
b = 11.347 (1) Å | θ = 2.3–28.3° |
c = 29.241 (3) Å | µ = 0.18 mm−1 |
β = 92.546 (2)° | T = 93 K |
V = 3173.8 (5) Å3 | Irregular, colorless |
Z = 12 | 0.45 × 0.22 × 0.12 mm |
Bruker SMART 1000 CCD area-detector diffractometer | 13028 independent reflections |
Radiation source: normal focus sealed tube | 10983 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ϕ and ω scans | θmax = 28.3°, θmin = 1.4° |
Absorption correction: integration (SHELXTL; Bruker 2001) | h = −12→12 |
Tmin = 0.922, Tmax = 0.979 | k = −14→14 |
25608 measured reflections | l = −35→38 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H-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 parameters | Δρmax = 0.52 e Å−3 |
1 restraint | Δρmin = −0.26 e Å−3 |
C6H6N4O10 | V = 3173.8 (5) Å3 |
Mr = 294.15 | Z = 12 |
Monoclinic, P21 | Mo Kα radiation |
a = 9.5746 (9) Å | µ = 0.18 mm−1 |
b = 11.347 (1) Å | T = 93 K |
c = 29.241 (3) Å | 0.45 × 0.22 × 0.12 mm |
β = 92.546 (2)° |
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 = 0.979 | Rint = 0.029 |
25608 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 1 restraint |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 0.89 | Δρmax = 0.52 e Å−3 |
13028 reflections | Δρmin = −0.26 e Å−3 |
1081 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.7474 (3) | 0.7821 (2) | 0.96469 (9) | 0.0111 (5) | |
H1A | 0.7689 | 0.7738 | 0.9324 | 0.013* | |
O2 | 0.7411 (2) | 0.90256 (17) | 0.97859 (7) | 0.0145 (4) | |
C3 | 0.6165 (3) | 0.9248 (3) | 1.00244 (9) | 0.0156 (6) | |
H3A | 0.5809 | 1.0033 | 0.9958 | 0.019* | |
H3B | 0.6336 | 0.9169 | 1.0352 | 0.019* | |
C4 | 0.5143 (3) | 0.8310 (2) | 0.98434 (9) | 0.0115 (5) | |
N4A | 0.3999 (2) | 0.8012 (2) | 1.01641 (8) | 0.0170 (5) | |
O4A | 0.3914 (2) | 0.8608 (2) | 1.05046 (7) | 0.0284 (5) | |
O4B | 0.3264 (2) | 0.7168 (2) | 1.00495 (8) | 0.0226 (5) | |
N4B | 0.4415 (2) | 0.8728 (2) | 0.94002 (8) | 0.0134 (5) | |
O4C | 0.3222 (2) | 0.9098 (2) | 0.94140 (7) | 0.0212 (5) | |
O4D | 0.5135 (2) | 0.8680 (2) | 0.90667 (7) | 0.0201 (4) | |
C5 | 0.6080 (3) | 0.7240 (2) | 0.97549 (9) | 0.0110 (5) | |
H5A | 0.5707 | 0.6743 | 0.9504 | 0.013* | |
O6 | 0.6295 (2) | 0.66020 (18) | 1.01752 (6) | 0.0152 (4) | |
C7 | 0.7669 (3) | 0.6821 (3) | 1.03756 (9) | 0.0145 (6) | |
H7A | 0.8047 | 0.6119 | 1.0525 | 0.017* | |
H7B | 0.7651 | 0.7455 | 1.0598 | 0.017* | |
C8 | 0.8533 (3) | 0.7169 (2) | 0.99663 (9) | 0.0121 (5) | |
N8A | 0.9080 (3) | 0.6074 (2) | 0.97344 (8) | 0.0147 (5) | |
O8A | 0.8218 (2) | 0.55481 (18) | 0.94906 (7) | 0.0179 (4) | |
O8B | 1.0296 (2) | 0.5804 (2) | 0.98126 (8) | 0.0229 (5) | |
N8B | 0.9794 (2) | 0.7912 (2) | 1.00924 (8) | 0.0143 (5) | |
O8C | 1.0165 (2) | 0.7961 (2) | 1.04939 (7) | 0.0222 (5) | |
O8D | 1.0351 (2) | 0.83997 (19) | 0.97747 (7) | 0.0189 (4) | |
C1A | −0.0577 (3) | 0.6007 (2) | 0.84852 (9) | 0.0107 (5) | |
H1AA | −0.0909 | 0.5287 | 0.8630 | 0.013* | |
O2A | −0.02962 (19) | 0.69369 (18) | 0.88088 (6) | 0.0139 (4) | |
C3A | 0.1028 (3) | 0.7485 (3) | 0.87306 (9) | 0.0150 (6) | |
H3AA | 0.1482 | 0.7749 | 0.9016 | 0.018* | |
H3AB | 0.0916 | 0.8151 | 0.8524 | 0.018* | |
C4A | 0.1855 (3) | 0.6499 (3) | 0.85155 (9) | 0.0135 (5) | |
N4AA | 0.3029 (3) | 0.6909 (2) | 0.82219 (8) | 0.0185 (5) | |
O4AA | 0.3145 (3) | 0.7956 (2) | 0.81530 (9) | 0.0347 (6) | |
O4BA | 0.3744 (2) | 0.6123 (2) | 0.80674 (7) | 0.0268 (5) | |
N4BA | 0.2533 (2) | 0.5734 (2) | 0.88862 (8) | 0.0156 (5) | |
O4CA | 0.1897 (2) | 0.4850 (2) | 0.89928 (7) | 0.0215 (5) | |
O4DA | 0.3626 (2) | 0.6082 (2) | 0.90666 (8) | 0.0288 (6) | |
C5A | 0.0761 (3) | 0.5803 (3) | 0.82240 (9) | 0.0119 (5) | |
H5AA | 0.0999 | 0.4966 | 0.8203 | 0.014* | |
O6A | 0.0571 (2) | 0.63390 (19) | 0.77838 (6) | 0.0165 (4) | |
C7A | −0.0671 (3) | 0.7060 (3) | 0.77668 (9) | 0.0172 (6) | |
H7AA | −0.1111 | 0.7066 | 0.7462 | 0.021* | |
H7AB | −0.0457 | 0.7863 | 0.7859 | 0.021* | |
C8A | −0.1601 (3) | 0.6460 (3) | 0.81062 (9) | 0.0137 (5) | |
N8AA | −0.2380 (3) | 0.5457 (2) | 0.78677 (8) | 0.0155 (5) | |
O8AA | −0.1808 (2) | 0.45007 (18) | 0.78872 (7) | 0.0212 (5) | |
O8BA | −0.3463 (2) | 0.5695 (2) | 0.76567 (8) | 0.0283 (5) | |
N8BA | −0.2691 (3) | 0.7220 (2) | 0.83167 (8) | 0.0169 (5) | |
O8CA | −0.2621 (3) | 0.8282 (2) | 0.82540 (8) | 0.0339 (6) | |
O8DA | −0.3498 (2) | 0.6708 (2) | 0.85547 (7) | 0.0233 (5) | |
C1B | 0.2723 (3) | 0.7564 (2) | 0.64048 (9) | 0.0108 (5) | |
H1BA | 0.2352 | 0.7034 | 0.6164 | 0.013* | |
O2B | 0.28881 (19) | 0.69885 (18) | 0.68363 (6) | 0.0139 (4) | |
C3B | 0.4243 (3) | 0.7234 (3) | 0.70494 (9) | 0.0130 (5) | |
H3BA | 0.4601 | 0.6555 | 0.7219 | 0.016* | |
H3BB | 0.4201 | 0.7901 | 0.7256 | 0.016* | |
C4B | 0.5154 (3) | 0.7514 (2) | 0.66449 (9) | 0.0115 (5) | |
N4AB | 0.6410 (2) | 0.8261 (2) | 0.67695 (8) | 0.0127 (5) | |
O4AB | 0.6743 (2) | 0.83470 (19) | 0.71781 (7) | 0.0200 (4) | |
O4BB | 0.7013 (2) | 0.86862 (19) | 0.64514 (7) | 0.0177 (4) | |
N4BB | 0.5718 (3) | 0.6375 (2) | 0.64442 (8) | 0.0138 (5) | |
O4CB | 0.6943 (2) | 0.61284 (19) | 0.65238 (8) | 0.0223 (5) | |
O4DB | 0.4848 (2) | 0.57985 (18) | 0.62275 (7) | 0.0191 (4) | |
C5B | 0.4143 (3) | 0.8100 (2) | 0.62874 (9) | 0.0107 (5) | |
H5BA | 0.4388 | 0.7918 | 0.5973 | 0.013* | |
O6B | 0.4081 (2) | 0.93369 (17) | 0.63671 (7) | 0.0148 (4) | |
C7B | 0.2828 (3) | 0.9648 (3) | 0.65868 (9) | 0.0149 (6) | |
H7BA | 0.2478 | 1.0404 | 0.6478 | 0.018* | |
H7BB | 0.2993 | 0.9689 | 0.6916 | 0.018* | |
C8B | 0.1799 (3) | 0.8664 (3) | 0.64578 (9) | 0.0131 (5) | |
N8AB | 0.1021 (2) | 0.8966 (2) | 0.60126 (8) | 0.0134 (5) | |
O8AB | 0.1664 (2) | 0.87608 (19) | 0.56706 (6) | 0.0182 (4) | |
O8BB | −0.0137 (2) | 0.9412 (2) | 0.60270 (7) | 0.0211 (5) | |
N8BB | 0.0700 (2) | 0.8431 (2) | 0.68031 (8) | 0.0152 (5) | |
O8CB | 0.0721 (2) | 0.9036 (2) | 0.71487 (7) | 0.0274 (5) | |
O8DB | −0.0100 (2) | 0.7621 (2) | 0.67099 (7) | 0.0200 (4) | |
C1C | 0.6017 (3) | 0.6045 (2) | 0.51792 (9) | 0.0107 (5) | |
H1CA | 0.5759 | 0.5327 | 0.5342 | 0.013* | |
O2C | 0.62420 (19) | 0.70275 (18) | 0.54808 (6) | 0.0137 (4) | |
C3C | 0.7528 (3) | 0.7621 (3) | 0.53860 (9) | 0.0145 (5) | |
H3CA | 0.7976 | 0.7934 | 0.5664 | 0.017* | |
H3CB | 0.7363 | 0.8260 | 0.5170 | 0.017* | |
C4C | 0.8409 (3) | 0.6659 (2) | 0.51821 (9) | 0.0124 (5) | |
N4AC | 0.9547 (2) | 0.7077 (2) | 0.48771 (8) | 0.0164 (5) | |
O4AC | 0.9552 (2) | 0.8113 (2) | 0.47753 (8) | 0.0302 (6) | |
O4BC | 1.0337 (2) | 0.6320 (2) | 0.47494 (7) | 0.0242 (5) | |
N4BC | 0.9139 (2) | 0.5950 (2) | 0.55646 (8) | 0.0144 (5) | |
O4CC | 1.0171 (2) | 0.6390 (2) | 0.57511 (7) | 0.0262 (5) | |
O4DC | 0.8594 (2) | 0.5026 (2) | 0.56688 (7) | 0.0220 (5) | |
C5C | 0.7351 (3) | 0.5884 (3) | 0.49087 (8) | 0.0121 (5) | |
H5CA | 0.7647 | 0.5059 | 0.4893 | 0.014* | |
O6C | 0.7085 (2) | 0.63959 (19) | 0.44642 (6) | 0.0155 (4) | |
C7C | 0.5772 (3) | 0.7020 (3) | 0.44469 (10) | 0.0196 (6) | |
H7CA | 0.5315 | 0.6968 | 0.4145 | 0.023* | |
H7CB | 0.5905 | 0.7843 | 0.4527 | 0.023* | |
C8C | 0.4932 (3) | 0.6387 (2) | 0.47998 (9) | 0.0131 (5) | |
N8AC | 0.4264 (3) | 0.5292 (2) | 0.45793 (8) | 0.0176 (5) | |
O8AC | 0.3165 (2) | 0.5413 (2) | 0.43630 (8) | 0.0265 (5) | |
O8BC | 0.4933 (2) | 0.4380 (2) | 0.46263 (7) | 0.0253 (5) | |
N8BC | 0.3716 (3) | 0.7048 (2) | 0.49816 (8) | 0.0193 (5) | |
O8CC | 0.3389 (2) | 0.7968 (2) | 0.48068 (8) | 0.0265 (5) | |
O8DC | 0.3139 (2) | 0.6564 (2) | 0.52969 (7) | 0.0253 (5) | |
C1D | −0.0568 (3) | 0.7540 (2) | 0.31042 (8) | 0.0098 (5) | |
H1DA | −0.0960 | 0.7002 | 0.2870 | 0.012* | |
O2D | −0.03320 (19) | 0.69704 (18) | 0.35343 (6) | 0.0132 (4) | |
C3D | 0.1045 (3) | 0.7231 (3) | 0.37243 (9) | 0.0131 (5) | |
H3DA | 0.1438 | 0.6557 | 0.3888 | 0.016* | |
H3DB | 0.1024 | 0.7898 | 0.3932 | 0.016* | |
C4D | 0.1887 (3) | 0.7521 (2) | 0.33080 (9) | 0.0120 (5) | |
N4AD | 0.3152 (2) | 0.8274 (2) | 0.34100 (8) | 0.0139 (5) | |
O4AD | 0.3514 (2) | 0.8391 (2) | 0.38137 (7) | 0.0203 (5) | |
O4BD | 0.3724 (2) | 0.86805 (19) | 0.30805 (7) | 0.0180 (4) | |
N4BD | 0.2443 (2) | 0.6377 (2) | 0.31033 (8) | 0.0144 (5) | |
O4CD | 0.3652 (2) | 0.61142 (19) | 0.31918 (8) | 0.0233 (5) | |
O4DD | 0.1581 (2) | 0.58172 (18) | 0.28765 (7) | 0.0178 (4) | |
C5D | 0.0821 (3) | 0.8096 (2) | 0.29646 (9) | 0.0101 (5) | |
H5DA | 0.1025 | 0.7925 | 0.2646 | 0.012* | |
O6D | 0.0757 (2) | 0.93289 (17) | 0.30534 (7) | 0.0148 (4) | |
C7D | −0.0464 (3) | 0.9621 (3) | 0.32940 (10) | 0.0159 (6) | |
H7DA | −0.0833 | 1.0382 | 0.3197 | 0.019* | |
H7DB | −0.0259 | 0.9640 | 0.3622 | 0.019* | |
C8D | −0.1502 (3) | 0.8632 (2) | 0.31665 (9) | 0.0124 (5) | |
N8AD | −0.2299 (2) | 0.8937 (2) | 0.27259 (7) | 0.0125 (5) | |
O8AD | −0.3439 (2) | 0.94119 (19) | 0.27512 (7) | 0.0211 (5) | |
O8BD | −0.1696 (2) | 0.87099 (19) | 0.23780 (7) | 0.0190 (4) | |
N8BD | −0.2577 (2) | 0.8384 (2) | 0.35187 (8) | 0.0157 (5) | |
O8CD | −0.2543 (2) | 0.8987 (2) | 0.38644 (7) | 0.0254 (5) | |
O8DD | −0.3380 (2) | 0.7579 (2) | 0.34257 (7) | 0.0209 (5) | |
C1E | 0.2773 (3) | 0.6021 (2) | 0.18613 (9) | 0.0099 (5) | |
H1EA | 0.2517 | 0.5343 | 0.2048 | 0.012* | |
O2E | 0.30123 (19) | 0.70436 (17) | 0.21379 (6) | 0.0129 (4) | |
C3E | 0.4285 (3) | 0.7615 (3) | 0.20131 (9) | 0.0144 (5) | |
H3EA | 0.4736 | 0.8011 | 0.2274 | 0.017* | |
H3EB | 0.4107 | 0.8182 | 0.1769 | 0.017* | |
C4E | 0.5175 (3) | 0.6586 (2) | 0.18516 (9) | 0.0126 (5) | |
N4AE | 0.6325 (2) | 0.6932 (2) | 0.15387 (8) | 0.0169 (5) | |
O4AE | 0.6389 (2) | 0.7946 (2) | 0.14153 (8) | 0.0295 (5) | |
O4BE | 0.7080 (2) | 0.6123 (2) | 0.14278 (8) | 0.0278 (5) | |
N4BE | 0.5883 (2) | 0.5956 (2) | 0.22558 (8) | 0.0153 (5) | |
O4CE | 0.6923 (3) | 0.6420 (2) | 0.24301 (8) | 0.0334 (6) | |
O4DE | 0.5331 (2) | 0.5069 (2) | 0.23893 (7) | 0.0234 (5) | |
C5E | 0.4120 (3) | 0.5772 (2) | 0.16058 (8) | 0.0106 (5) | |
H5EA | 0.4399 | 0.4941 | 0.1614 | 0.013* | |
O6E | 0.3890 (2) | 0.62222 (18) | 0.11537 (6) | 0.0143 (4) | |
C7E | 0.2465 (3) | 0.5975 (3) | 0.10231 (9) | 0.0183 (6) | |
H7EA | 0.2350 | 0.5159 | 0.0929 | 0.022* | |
H7EB | 0.2136 | 0.6483 | 0.0774 | 0.022* | |
C8E | 0.1678 (3) | 0.6224 (2) | 0.14578 (9) | 0.0128 (5) | |
N8AE | 0.0419 (3) | 0.5420 (2) | 0.14822 (8) | 0.0188 (5) | |
O8AE | 0.0079 (2) | 0.5065 (2) | 0.18562 (7) | 0.0265 (5) | |
O8BE | −0.0189 (2) | 0.5210 (2) | 0.11127 (7) | 0.0222 (5) | |
N8BE | 0.1099 (3) | 0.7468 (2) | 0.14659 (8) | 0.0172 (5) | |
O8CE | −0.0009 (2) | 0.7625 (2) | 0.16355 (8) | 0.0258 (5) | |
O8DE | 0.1855 (2) | 0.82098 (19) | 0.13063 (7) | 0.0215 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0124 (12) | 0.0104 (13) | 0.0103 (12) | −0.0021 (10) | −0.0005 (10) | 0.0009 (10) |
O2 | 0.0132 (9) | 0.0092 (10) | 0.0210 (10) | 0.0011 (8) | 0.0013 (8) | −0.0017 (8) |
C3 | 0.0150 (13) | 0.0157 (15) | 0.0160 (13) | 0.0022 (11) | 0.0007 (11) | −0.0048 (11) |
C4 | 0.0115 (12) | 0.0102 (13) | 0.0130 (12) | 0.0005 (10) | 0.0049 (10) | −0.0005 (10) |
N4A | 0.0151 (12) | 0.0180 (13) | 0.0184 (12) | 0.0060 (10) | 0.0044 (10) | 0.0041 (10) |
O4A | 0.0300 (12) | 0.0341 (14) | 0.0220 (11) | 0.0042 (10) | 0.0128 (10) | −0.0063 (10) |
O4B | 0.0174 (10) | 0.0196 (12) | 0.0311 (12) | −0.0023 (9) | 0.0064 (9) | 0.0036 (9) |
N4B | 0.0146 (11) | 0.0090 (11) | 0.0163 (11) | −0.0009 (9) | −0.0030 (9) | 0.0001 (9) |
O4C | 0.0139 (10) | 0.0200 (11) | 0.0292 (11) | 0.0022 (9) | −0.0037 (9) | 0.0017 (9) |
O4D | 0.0235 (11) | 0.0206 (11) | 0.0164 (10) | 0.0006 (9) | 0.0018 (9) | 0.0039 (8) |
C5 | 0.0119 (12) | 0.0109 (13) | 0.0101 (12) | −0.0003 (10) | −0.0015 (10) | 0.0017 (10) |
O6 | 0.0122 (9) | 0.0182 (11) | 0.0153 (9) | −0.0007 (8) | 0.0001 (8) | 0.0066 (8) |
C7 | 0.0122 (13) | 0.0206 (15) | 0.0108 (12) | 0.0005 (11) | 0.0005 (10) | 0.0031 (11) |
C8 | 0.0121 (12) | 0.0126 (13) | 0.0115 (12) | 0.0016 (11) | 0.0006 (10) | −0.0001 (10) |
N8A | 0.0168 (12) | 0.0101 (12) | 0.0174 (11) | 0.0018 (9) | 0.0034 (10) | 0.0006 (9) |
O8A | 0.0205 (10) | 0.0151 (10) | 0.0180 (10) | −0.0013 (8) | −0.0004 (8) | −0.0053 (8) |
O8B | 0.0156 (11) | 0.0205 (12) | 0.0325 (12) | 0.0072 (9) | −0.0003 (9) | −0.0024 (9) |
N8B | 0.0099 (11) | 0.0156 (12) | 0.0173 (12) | 0.0021 (9) | −0.0017 (9) | −0.0037 (9) |
O8C | 0.0232 (11) | 0.0261 (12) | 0.0165 (10) | −0.0036 (9) | −0.0076 (8) | 0.0015 (9) |
O8D | 0.0145 (10) | 0.0200 (11) | 0.0226 (10) | −0.0030 (8) | 0.0052 (8) | 0.0003 (9) |
C1A | 0.0130 (13) | 0.0085 (13) | 0.0105 (12) | 0.0015 (10) | 0.0003 (10) | −0.0014 (10) |
O2A | 0.0130 (9) | 0.0156 (10) | 0.0132 (9) | −0.0014 (8) | 0.0013 (7) | −0.0055 (8) |
C3A | 0.0143 (13) | 0.0150 (14) | 0.0162 (13) | −0.0029 (11) | 0.0043 (11) | −0.0035 (11) |
C4A | 0.0142 (13) | 0.0180 (14) | 0.0082 (12) | −0.0001 (11) | −0.0001 (10) | −0.0001 (10) |
N4AA | 0.0154 (12) | 0.0273 (15) | 0.0129 (11) | −0.0040 (11) | 0.0020 (9) | −0.0004 (10) |
O4AA | 0.0376 (14) | 0.0299 (14) | 0.0377 (13) | −0.0114 (12) | 0.0151 (11) | 0.0059 (11) |
O4BA | 0.0191 (11) | 0.0402 (15) | 0.0215 (11) | 0.0029 (10) | 0.0068 (9) | −0.0036 (10) |
N4BA | 0.0142 (12) | 0.0193 (14) | 0.0131 (11) | 0.0024 (10) | −0.0006 (9) | −0.0015 (10) |
O4CA | 0.0242 (11) | 0.0193 (12) | 0.0207 (10) | −0.0004 (9) | −0.0021 (9) | 0.0044 (9) |
O4DA | 0.0204 (12) | 0.0422 (16) | 0.0227 (11) | −0.0089 (10) | −0.0113 (9) | 0.0049 (10) |
C5A | 0.0130 (13) | 0.0127 (13) | 0.0100 (12) | 0.0008 (11) | −0.0006 (10) | −0.0009 (10) |
O6A | 0.0148 (10) | 0.0261 (12) | 0.0086 (9) | 0.0009 (8) | 0.0015 (7) | 0.0009 (8) |
C7A | 0.0179 (14) | 0.0193 (15) | 0.0144 (13) | 0.0012 (12) | −0.0004 (11) | 0.0059 (11) |
C8A | 0.0148 (13) | 0.0126 (14) | 0.0135 (12) | 0.0015 (11) | −0.0007 (11) | −0.0004 (10) |
N8AA | 0.0166 (12) | 0.0191 (13) | 0.0107 (10) | −0.0013 (10) | 0.0010 (9) | −0.0007 (9) |
O8AA | 0.0315 (12) | 0.0138 (11) | 0.0178 (10) | 0.0014 (9) | −0.0044 (9) | −0.0019 (8) |
O8BA | 0.0181 (11) | 0.0335 (14) | 0.0322 (12) | 0.0037 (10) | −0.0102 (10) | −0.0102 (11) |
N8BA | 0.0169 (12) | 0.0194 (13) | 0.0141 (11) | 0.0066 (10) | −0.0008 (10) | −0.0031 (10) |
O8CA | 0.0473 (16) | 0.0167 (12) | 0.0387 (14) | 0.0134 (11) | 0.0120 (12) | 0.0033 (10) |
O8DA | 0.0159 (10) | 0.0291 (13) | 0.0254 (11) | 0.0002 (9) | 0.0071 (9) | −0.0046 (9) |
C1B | 0.0115 (12) | 0.0106 (13) | 0.0102 (11) | −0.0004 (10) | −0.0003 (10) | 0.0004 (10) |
O2B | 0.0113 (9) | 0.0175 (11) | 0.0129 (9) | −0.0019 (8) | −0.0007 (7) | 0.0066 (8) |
C3B | 0.0111 (12) | 0.0179 (14) | 0.0098 (12) | −0.0027 (11) | −0.0019 (10) | 0.0025 (10) |
C4B | 0.0100 (12) | 0.0122 (13) | 0.0121 (12) | 0.0003 (10) | −0.0014 (10) | 0.0015 (10) |
N4AB | 0.0107 (11) | 0.0089 (11) | 0.0184 (11) | 0.0009 (9) | 0.0002 (9) | 0.0015 (9) |
O4AB | 0.0211 (11) | 0.0242 (12) | 0.0140 (10) | −0.0027 (9) | −0.0055 (8) | 0.0022 (9) |
O4BB | 0.0140 (10) | 0.0180 (11) | 0.0215 (10) | −0.0021 (8) | 0.0037 (8) | 0.0023 (8) |
N4BB | 0.0144 (12) | 0.0114 (12) | 0.0157 (11) | 0.0013 (9) | 0.0019 (9) | 0.0020 (9) |
O4CB | 0.0147 (10) | 0.0187 (12) | 0.0330 (12) | 0.0058 (8) | −0.0039 (9) | −0.0012 (9) |
O4DB | 0.0208 (11) | 0.0136 (11) | 0.0229 (10) | −0.0025 (9) | 0.0002 (9) | −0.0035 (8) |
C5B | 0.0099 (12) | 0.0109 (13) | 0.0113 (12) | 0.0012 (10) | −0.0005 (10) | 0.0019 (10) |
O6B | 0.0130 (9) | 0.0087 (10) | 0.0229 (10) | 0.0018 (7) | 0.0017 (8) | −0.0005 (8) |
C7B | 0.0114 (13) | 0.0161 (14) | 0.0169 (13) | 0.0012 (11) | −0.0023 (11) | −0.0039 (11) |
C8B | 0.0120 (13) | 0.0158 (14) | 0.0113 (12) | 0.0007 (11) | −0.0009 (10) | −0.0005 (10) |
N8AB | 0.0141 (11) | 0.0089 (11) | 0.0168 (11) | −0.0014 (9) | −0.0032 (9) | 0.0023 (9) |
O8AB | 0.0234 (11) | 0.0181 (11) | 0.0132 (9) | 0.0003 (9) | 0.0029 (8) | 0.0044 (8) |
O8BB | 0.0144 (10) | 0.0241 (12) | 0.0244 (11) | 0.0042 (9) | −0.0040 (9) | 0.0053 (9) |
N8BB | 0.0156 (12) | 0.0166 (13) | 0.0136 (11) | 0.0053 (10) | 0.0040 (9) | 0.0026 (9) |
O8CB | 0.0351 (13) | 0.0291 (13) | 0.0189 (11) | 0.0017 (11) | 0.0133 (10) | −0.0064 (9) |
O8DB | 0.0146 (10) | 0.0231 (12) | 0.0223 (10) | −0.0009 (9) | 0.0018 (8) | 0.0055 (9) |
C1C | 0.0128 (13) | 0.0105 (13) | 0.0090 (11) | 0.0004 (10) | 0.0005 (10) | −0.0026 (10) |
O2C | 0.0133 (9) | 0.0137 (10) | 0.0141 (9) | −0.0006 (8) | 0.0017 (7) | −0.0049 (8) |
C3C | 0.0117 (12) | 0.0128 (13) | 0.0189 (13) | 0.0003 (11) | 0.0002 (11) | −0.0014 (11) |
C4C | 0.0126 (13) | 0.0124 (14) | 0.0123 (12) | 0.0002 (10) | 0.0015 (10) | 0.0004 (10) |
N4AC | 0.0145 (12) | 0.0209 (14) | 0.0138 (11) | −0.0049 (10) | 0.0004 (9) | −0.0001 (10) |
O4AC | 0.0286 (13) | 0.0265 (14) | 0.0362 (13) | −0.0061 (10) | 0.0092 (11) | 0.0100 (11) |
O4BC | 0.0190 (11) | 0.0339 (14) | 0.0203 (11) | 0.0008 (10) | 0.0072 (9) | −0.0021 (10) |
N4BC | 0.0151 (12) | 0.0152 (13) | 0.0129 (11) | 0.0025 (10) | 0.0007 (9) | −0.0012 (9) |
O4CC | 0.0221 (11) | 0.0347 (14) | 0.0208 (11) | −0.0098 (10) | −0.0119 (9) | 0.0048 (10) |
O4DC | 0.0248 (11) | 0.0191 (12) | 0.0217 (10) | 0.0001 (9) | −0.0042 (9) | 0.0079 (9) |
C5C | 0.0141 (13) | 0.0132 (13) | 0.0090 (11) | 0.0002 (11) | 0.0009 (10) | 0.0000 (10) |
O6C | 0.0120 (9) | 0.0227 (11) | 0.0119 (9) | 0.0012 (8) | −0.0001 (7) | 0.0013 (8) |
C7C | 0.0169 (14) | 0.0259 (17) | 0.0158 (13) | −0.0011 (13) | −0.0008 (11) | 0.0052 (12) |
C8C | 0.0149 (13) | 0.0115 (13) | 0.0127 (12) | 0.0018 (11) | −0.0021 (10) | −0.0038 (10) |
N8AC | 0.0193 (13) | 0.0172 (13) | 0.0159 (11) | 0.0003 (10) | −0.0016 (10) | −0.0016 (10) |
O8AC | 0.0206 (11) | 0.0273 (13) | 0.0304 (12) | 0.0028 (10) | −0.0110 (10) | −0.0047 (10) |
O8BC | 0.0268 (12) | 0.0179 (12) | 0.0305 (12) | 0.0024 (9) | −0.0075 (10) | −0.0043 (9) |
N8BC | 0.0158 (12) | 0.0240 (14) | 0.0178 (12) | 0.0040 (11) | −0.0033 (10) | −0.0040 (11) |
O8CC | 0.0282 (12) | 0.0217 (12) | 0.0292 (12) | 0.0111 (10) | −0.0041 (10) | −0.0015 (10) |
O8DC | 0.0198 (11) | 0.0347 (14) | 0.0219 (11) | −0.0009 (10) | 0.0063 (9) | −0.0033 (10) |
C1D | 0.0101 (12) | 0.0084 (12) | 0.0110 (12) | 0.0006 (10) | 0.0011 (10) | 0.0012 (10) |
O2D | 0.0105 (9) | 0.0169 (10) | 0.0119 (9) | −0.0024 (8) | −0.0021 (7) | 0.0049 (8) |
C3D | 0.0097 (12) | 0.0197 (15) | 0.0098 (12) | 0.0006 (10) | 0.0009 (10) | 0.0023 (10) |
C4D | 0.0112 (12) | 0.0125 (13) | 0.0123 (12) | −0.0001 (10) | 0.0013 (10) | 0.0022 (10) |
N4AD | 0.0125 (11) | 0.0093 (11) | 0.0197 (12) | 0.0020 (9) | −0.0007 (9) | 0.0000 (9) |
O4AD | 0.0194 (10) | 0.0251 (12) | 0.0158 (10) | −0.0057 (9) | −0.0062 (8) | −0.0007 (9) |
O4BD | 0.0141 (10) | 0.0202 (11) | 0.0202 (10) | −0.0030 (8) | 0.0041 (8) | 0.0028 (8) |
N4BD | 0.0138 (12) | 0.0133 (12) | 0.0164 (11) | 0.0020 (9) | 0.0018 (9) | 0.0019 (9) |
O4CD | 0.0166 (11) | 0.0189 (12) | 0.0343 (12) | 0.0073 (9) | −0.0011 (9) | −0.0020 (9) |
O4DD | 0.0217 (11) | 0.0144 (11) | 0.0172 (10) | −0.0023 (9) | −0.0007 (8) | −0.0029 (8) |
C5D | 0.0109 (12) | 0.0092 (13) | 0.0100 (11) | −0.0011 (10) | −0.0005 (10) | −0.0019 (9) |
O6D | 0.0120 (9) | 0.0095 (10) | 0.0231 (10) | 0.0007 (8) | 0.0014 (8) | −0.0012 (8) |
C7D | 0.0141 (13) | 0.0121 (14) | 0.0213 (14) | 0.0003 (11) | 0.0000 (11) | −0.0051 (11) |
C8D | 0.0122 (13) | 0.0150 (14) | 0.0100 (12) | −0.0001 (10) | 0.0009 (10) | 0.0004 (10) |
N8AD | 0.0150 (12) | 0.0092 (11) | 0.0131 (11) | −0.0030 (9) | −0.0015 (9) | 0.0034 (9) |
O8AD | 0.0168 (10) | 0.0210 (12) | 0.0253 (11) | 0.0051 (9) | −0.0023 (9) | 0.0048 (9) |
O8BD | 0.0253 (11) | 0.0176 (11) | 0.0141 (9) | −0.0029 (9) | 0.0017 (8) | 0.0047 (8) |
N8BD | 0.0143 (12) | 0.0190 (13) | 0.0142 (11) | 0.0042 (10) | 0.0028 (9) | 0.0044 (10) |
O8CD | 0.0294 (12) | 0.0296 (13) | 0.0177 (10) | 0.0035 (10) | 0.0077 (9) | −0.0053 (9) |
O8DD | 0.0150 (10) | 0.0214 (12) | 0.0264 (11) | 0.0000 (9) | 0.0038 (9) | 0.0059 (9) |
C1E | 0.0121 (12) | 0.0078 (12) | 0.0097 (11) | 0.0011 (10) | −0.0016 (10) | −0.0007 (10) |
O2E | 0.0149 (9) | 0.0114 (10) | 0.0124 (9) | −0.0022 (8) | 0.0020 (7) | −0.0041 (7) |
C3E | 0.0154 (13) | 0.0125 (14) | 0.0152 (13) | −0.0016 (11) | −0.0021 (11) | −0.0006 (11) |
C4E | 0.0143 (13) | 0.0131 (14) | 0.0105 (12) | −0.0021 (10) | 0.0015 (10) | −0.0003 (10) |
N4AE | 0.0137 (11) | 0.0224 (14) | 0.0147 (11) | −0.0044 (10) | 0.0029 (9) | 0.0016 (10) |
O4AE | 0.0298 (12) | 0.0273 (13) | 0.0323 (12) | −0.0068 (10) | 0.0105 (10) | 0.0105 (10) |
O4BE | 0.0197 (11) | 0.0329 (14) | 0.0316 (12) | 0.0031 (10) | 0.0100 (10) | −0.0007 (10) |
N4BE | 0.0165 (12) | 0.0156 (13) | 0.0136 (11) | 0.0009 (10) | −0.0017 (9) | −0.0003 (9) |
O4CE | 0.0297 (13) | 0.0364 (15) | 0.0321 (13) | −0.0127 (11) | −0.0196 (11) | 0.0095 (11) |
O4DE | 0.0267 (12) | 0.0227 (12) | 0.0204 (10) | −0.0037 (10) | −0.0052 (9) | 0.0117 (9) |
C5E | 0.0110 (12) | 0.0120 (13) | 0.0088 (11) | 0.0009 (10) | 0.0010 (10) | −0.0015 (10) |
O6E | 0.0152 (10) | 0.0192 (11) | 0.0085 (8) | −0.0011 (8) | 0.0009 (7) | 0.0018 (7) |
C7E | 0.0194 (15) | 0.0215 (16) | 0.0137 (13) | 0.0021 (12) | −0.0021 (11) | 0.0001 (11) |
C8E | 0.0122 (13) | 0.0119 (14) | 0.0140 (12) | −0.0024 (10) | −0.0025 (10) | −0.0023 (10) |
N8AE | 0.0158 (12) | 0.0167 (13) | 0.0238 (13) | 0.0008 (10) | −0.0017 (10) | −0.0002 (10) |
O8AE | 0.0249 (12) | 0.0307 (13) | 0.0240 (11) | −0.0060 (10) | 0.0026 (9) | 0.0033 (10) |
O8BE | 0.0190 (11) | 0.0268 (12) | 0.0200 (10) | −0.0020 (9) | −0.0077 (9) | −0.0064 (9) |
N8BE | 0.0223 (13) | 0.0165 (13) | 0.0125 (11) | 0.0018 (10) | −0.0042 (10) | −0.0022 (9) |
O8CE | 0.0159 (10) | 0.0277 (13) | 0.0338 (12) | 0.0040 (9) | 0.0021 (9) | −0.0109 (10) |
O8DE | 0.0316 (12) | 0.0168 (11) | 0.0162 (10) | −0.0022 (9) | 0.0005 (9) | 0.0023 (8) |
C1—O2 | 1.429 (3) | C1C—O2C | 1.432 (3) |
C1—C5 | 1.534 (4) | C1C—C8C | 1.536 (4) |
C1—C8 | 1.537 (4) | C1C—C5C | 1.542 (3) |
C1—H1A | 0.9800 | C1C—H1CA | 0.9800 |
O2—C3 | 1.431 (3) | O2C—C3C | 1.441 (3) |
C3—C4 | 1.525 (4) | C3C—C4C | 1.519 (4) |
C3—H3A | 0.9700 | C3C—H3CA | 0.9700 |
C3—H3B | 0.9700 | C3C—H3CB | 0.9700 |
C4—N4A | 1.511 (3) | C4C—N4AC | 1.515 (3) |
C4—N4B | 1.520 (3) | C4C—N4BC | 1.521 (4) |
C4—C5 | 1.538 (4) | C4C—C5C | 1.538 (4) |
N4A—O4A | 1.210 (3) | N4AC—O4AC | 1.213 (3) |
N4A—O4B | 1.226 (3) | N4AC—O4BC | 1.214 (3) |
N4B—O4C | 1.219 (3) | N4BC—O4CC | 1.215 (3) |
N4B—O4D | 1.221 (3) | N4BC—O4DC | 1.216 (3) |
C5—O6 | 1.433 (3) | C5C—O6C | 1.436 (3) |
C5—H5A | 0.9800 | C5C—H5CA | 0.9800 |
O6—C7 | 1.438 (3) | O6C—C7C | 1.442 (3) |
C7—C8 | 1.537 (4) | C7C—C8C | 1.517 (4) |
C7—H7A | 0.9700 | C7C—H7CA | 0.9700 |
C7—H7B | 0.9700 | C7C—H7CB | 0.9700 |
C8—N8B | 1.505 (4) | C8C—N8BC | 1.502 (4) |
C8—N8A | 1.519 (3) | C8C—N8AC | 1.527 (4) |
N8A—O8B | 1.216 (3) | N8AC—O8AC | 1.211 (3) |
N8A—O8A | 1.222 (3) | N8AC—O8BC | 1.222 (3) |
N8B—O8C | 1.212 (3) | N8BC—O8CC | 1.198 (3) |
N8B—O8D | 1.224 (3) | N8BC—O8DC | 1.225 (3) |
C1A—O2A | 1.435 (3) | C1D—O2D | 1.423 (3) |
C1A—C8A | 1.535 (4) | C1D—C8D | 1.543 (4) |
C1A—C5A | 1.538 (4) | C1D—C5D | 1.544 (4) |
C1A—H1AA | 0.9800 | C1D—H1DA | 0.9800 |
O2A—C3A | 1.440 (3) | O2D—C3D | 1.439 (3) |
C3A—C4A | 1.523 (4) | C3D—C4D | 1.525 (3) |
C3A—H3AA | 0.9700 | C3D—H3DA | 0.9700 |
C3A—H3AB | 0.9700 | C3D—H3DB | 0.9700 |
C4A—N4BA | 1.512 (4) | C4D—N4AD | 1.501 (4) |
C4A—N4AA | 1.518 (4) | C4D—N4BD | 1.535 (4) |
C4A—C5A | 1.539 (4) | C4D—C5D | 1.544 (4) |
N4AA—O4AA | 1.211 (4) | N4AD—O4BD | 1.220 (3) |
N4AA—O4BA | 1.222 (3) | N4AD—O4AD | 1.223 (3) |
N4BA—O4DA | 1.217 (3) | N4BD—O4CD | 1.213 (3) |
N4BA—O4CA | 1.221 (3) | N4BD—O4DD | 1.215 (3) |
C5A—O6A | 1.428 (3) | C5D—O6D | 1.424 (3) |
C5A—H5AA | 0.9800 | C5D—H5DA | 0.9800 |
O6A—C7A | 1.442 (3) | O6D—C7D | 1.430 (3) |
C7A—C8A | 1.523 (4) | C7D—C8D | 1.534 (4) |
C7A—H7AA | 0.9700 | C7D—H7DA | 0.9700 |
C7A—H7AB | 0.9700 | C7D—H7DB | 0.9700 |
C8A—N8BA | 1.506 (4) | C8D—N8AD | 1.508 (3) |
C8A—N8AA | 1.514 (4) | C8D—N8BD | 1.514 (3) |
N8AA—O8BA | 1.213 (3) | N8AD—O8BD | 1.219 (3) |
N8AA—O8AA | 1.216 (3) | N8AD—O8AD | 1.222 (3) |
N8BA—O8DA | 1.211 (3) | N8BD—O8DD | 1.217 (3) |
N8BA—O8CA | 1.221 (4) | N8BD—O8CD | 1.220 (3) |
C1B—O2B | 1.423 (3) | C1E—O2E | 1.427 (3) |
C1B—C8B | 1.542 (4) | C1E—C5E | 1.545 (3) |
C1B—C5B | 1.542 (4) | C1E—C8E | 1.560 (4) |
C1B—H1BA | 0.9800 | C1E—H1EA | 0.9800 |
O2B—C3B | 1.441 (3) | O2E—C3E | 1.442 (3) |
C3B—C4B | 1.534 (4) | C3E—C4E | 1.533 (4) |
C3B—H3BA | 0.9700 | C3E—H3EA | 0.9700 |
C3B—H3BB | 0.9700 | C3E—H3EB | 0.9700 |
C4B—N4AB | 1.502 (3) | C4E—N4AE | 1.514 (3) |
C4B—N4BB | 1.528 (4) | C4E—N4BE | 1.515 (4) |
C4B—C5B | 1.543 (4) | C4E—C5E | 1.525 (4) |
N4AB—O4BB | 1.217 (3) | N4AE—O4AE | 1.209 (4) |
N4AB—O4AB | 1.227 (3) | N4AE—O4BE | 1.221 (3) |
N4BB—O4DB | 1.215 (3) | N4BE—O4DE | 1.209 (3) |
N4BB—O4CB | 1.218 (3) | N4BE—O4CE | 1.219 (3) |
C5B—O6B | 1.424 (3) | C5E—O6E | 1.425 (3) |
C5B—H5BA | 0.9800 | C5E—H5EA | 0.9800 |
O6B—C7B | 1.430 (3) | O6E—C7E | 1.429 (3) |
C7B—C8B | 1.526 (4) | C7E—C8E | 1.532 (4) |
C7B—H7BA | 0.9700 | C7E—H7EA | 0.9700 |
C7B—H7BB | 0.9700 | C7E—H7EB | 0.9700 |
C8B—N8AB | 1.510 (3) | C8E—N8AE | 1.516 (4) |
C8B—N8BB | 1.513 (3) | C8E—N8BE | 1.517 (4) |
N8AB—O8AB | 1.220 (3) | N8AE—O8AE | 1.223 (3) |
N8AB—O8BB | 1.221 (3) | N8AE—O8BE | 1.228 (3) |
N8BB—O8DB | 1.219 (3) | N8BE—O8CE | 1.204 (3) |
N8BB—O8CB | 1.221 (3) | N8BE—O8DE | 1.217 (3) |
O2—C1—C5 | 107.7 (2) | O2C—C1C—C8C | 109.0 (2) |
O2—C1—C8 | 108.8 (2) | O2C—C1C—C5C | 107.6 (2) |
C5—C1—C8 | 103.0 (2) | C8C—C1C—C5C | 102.0 (2) |
O2—C1—H1A | 112.3 | O2C—C1C—H1CA | 112.5 |
C5—C1—H1A | 112.3 | C8C—C1C—H1CA | 112.5 |
C8—C1—H1A | 112.3 | C5C—C1C—H1CA | 112.5 |
C1—O2—C3 | 110.7 (2) | C1C—O2C—C3C | 110.60 (19) |
O2—C3—C4 | 104.1 (2) | O2C—C3C—C4C | 103.5 (2) |
O2—C3—H3A | 110.9 | O2C—C3C—H3CA | 111.1 |
C4—C3—H3A | 110.9 | C4C—C3C—H3CA | 111.1 |
O2—C3—H3B | 110.9 | O2C—C3C—H3CB | 111.1 |
C4—C3—H3B | 110.9 | C4C—C3C—H3CB | 111.1 |
H3A—C3—H3B | 108.9 | H3CA—C3C—H3CB | 109.0 |
N4A—C4—N4B | 106.4 (2) | N4AC—C4C—C3C | 115.6 (2) |
N4A—C4—C3 | 114.4 (2) | N4AC—C4C—N4BC | 106.3 (2) |
N4B—C4—C3 | 109.9 (2) | C3C—C4C—N4BC | 109.7 (2) |
N4A—C4—C5 | 111.8 (2) | N4AC—C4C—C5C | 110.3 (2) |
N4B—C4—C5 | 110.6 (2) | C3C—C4C—C5C | 104.5 (2) |
C3—C4—C5 | 103.8 (2) | N4BC—C4C—C5C | 110.5 (2) |
O4A—N4A—O4B | 127.0 (2) | O4AC—N4AC—O4BC | 127.0 (3) |
O4A—N4A—C4 | 117.6 (2) | O4AC—N4AC—C4C | 117.3 (2) |
O4B—N4A—C4 | 115.4 (2) | O4BC—N4AC—C4C | 115.7 (2) |
O4C—N4B—O4D | 127.2 (2) | O4CC—N4BC—O4DC | 126.3 (3) |
O4C—N4B—C4 | 118.3 (2) | O4CC—N4BC—C4C | 116.8 (2) |
O4D—N4B—C4 | 114.4 (2) | O4DC—N4BC—C4C | 116.9 (2) |
O6—C5—C1 | 107.5 (2) | O6C—C5C—C4C | 109.0 (2) |
O6—C5—C4 | 108.5 (2) | O6C—C5C—C1C | 107.4 (2) |
C1—C5—C4 | 102.5 (2) | C4C—C5C—C1C | 102.0 (2) |
O6—C5—H5A | 112.6 | O6C—C5C—H5CA | 112.6 |
C1—C5—H5A | 112.6 | C4C—C5C—H5CA | 112.6 |
C4—C5—H5A | 112.6 | C1C—C5C—H5CA | 112.6 |
C5—O6—C7 | 110.8 (2) | C5C—O6C—C7C | 110.45 (19) |
O6—C7—C8 | 104.0 (2) | O6C—C7C—C8C | 103.4 (2) |
O6—C7—H7A | 111.0 | O6C—C7C—H7CA | 111.1 |
C8—C7—H7A | 111.0 | C8C—C7C—H7CA | 111.1 |
O6—C7—H7B | 111.0 | O6C—C7C—H7CB | 111.1 |
C8—C7—H7B | 111.0 | C8C—C7C—H7CB | 111.1 |
H7A—C7—H7B | 109.0 | H7CA—C7C—H7CB | 109.1 |
N8B—C8—N8A | 106.2 (2) | N8BC—C8C—C7C | 116.6 (2) |
N8B—C8—C7 | 114.0 (2) | N8BC—C8C—N8AC | 103.8 (2) |
N8A—C8—C7 | 110.2 (2) | C7C—C8C—N8AC | 108.8 (2) |
N8B—C8—C1 | 112.3 (2) | N8BC—C8C—C1C | 112.4 (2) |
N8A—C8—C1 | 110.7 (2) | C7C—C8C—C1C | 104.4 (2) |
C7—C8—C1 | 103.5 (2) | N8AC—C8C—C1C | 110.9 (2) |
O8B—N8A—O8A | 127.1 (2) | O8AC—N8AC—O8BC | 126.4 (3) |
O8B—N8A—C8 | 117.9 (2) | O8AC—N8AC—C8C | 117.8 (2) |
O8A—N8A—C8 | 115.0 (2) | O8BC—N8AC—C8C | 115.7 (2) |
O8C—N8B—O8D | 126.6 (2) | O8CC—N8BC—O8DC | 126.4 (3) |
O8C—N8B—C8 | 117.4 (2) | O8CC—N8BC—C8C | 118.4 (2) |
O8D—N8B—C8 | 116.0 (2) | O8DC—N8BC—C8C | 115.2 (3) |
O2A—C1A—C8A | 109.0 (2) | O2D—C1D—C8D | 109.3 (2) |
O2A—C1A—C5A | 107.6 (2) | O2D—C1D—C5D | 108.3 (2) |
C8A—C1A—C5A | 102.2 (2) | C8D—C1D—C5D | 102.3 (2) |
O2A—C1A—H1AA | 112.5 | O2D—C1D—H1DA | 112.1 |
C8A—C1A—H1AA | 112.5 | C8D—C1D—H1DA | 112.1 |
C5A—C1A—H1AA | 112.5 | C5D—C1D—H1DA | 112.1 |
C1A—O2A—C3A | 110.71 (19) | C1D—O2D—C3D | 110.78 (19) |
O2A—C3A—C4A | 103.1 (2) | O2D—C3D—C4D | 104.1 (2) |
O2A—C3A—H3AA | 111.1 | O2D—C3D—H3DA | 110.9 |
C4A—C3A—H3AA | 111.1 | C4D—C3D—H3DA | 110.9 |
O2A—C3A—H3AB | 111.1 | O2D—C3D—H3DB | 110.9 |
C4A—C3A—H3AB | 111.1 | C4D—C3D—H3DB | 110.9 |
H3AA—C3A—H3AB | 109.1 | H3DA—C3D—H3DB | 109.0 |
N4BA—C4A—N4AA | 106.1 (2) | N4AD—C4D—C3D | 114.5 (2) |
N4BA—C4A—C3A | 109.9 (2) | N4AD—C4D—N4BD | 105.5 (2) |
N4AA—C4A—C3A | 114.8 (2) | C3D—C4D—N4BD | 109.5 (2) |
N4BA—C4A—C5A | 111.3 (2) | N4AD—C4D—C5D | 113.1 (2) |
N4AA—C4A—C5A | 110.3 (2) | C3D—C4D—C5D | 104.6 (2) |
C3A—C4A—C5A | 104.6 (2) | N4BD—C4D—C5D | 109.5 (2) |
O4AA—N4AA—O4BA | 126.7 (3) | O4BD—N4AD—O4AD | 127.1 (2) |
O4AA—N4AA—C4A | 118.1 (3) | O4BD—N4AD—C4D | 116.4 (2) |
O4BA—N4AA—C4A | 115.2 (3) | O4AD—N4AD—C4D | 116.4 (2) |
O4DA—N4BA—O4CA | 125.8 (3) | O4CD—N4BD—O4DD | 127.4 (3) |
O4DA—N4BA—C4A | 117.2 (2) | O4CD—N4BD—C4D | 118.0 (2) |
O4CA—N4BA—C4A | 116.8 (2) | O4DD—N4BD—C4D | 114.6 (2) |
O6A—C5A—C1A | 107.9 (2) | O6D—C5D—C1D | 108.0 (2) |
O6A—C5A—C4A | 109.7 (2) | O6D—C5D—C4D | 109.2 (2) |
C1A—C5A—C4A | 102.1 (2) | C1D—C5D—C4D | 102.0 (2) |
O6A—C5A—H5AA | 112.2 | O6D—C5D—H5DA | 112.4 |
C1A—C5A—H5AA | 112.2 | C1D—C5D—H5DA | 112.4 |
C4A—C5A—H5AA | 112.2 | C4D—C5D—H5DA | 112.4 |
C5A—O6A—C7A | 110.15 (19) | C5D—O6D—C7D | 111.1 (2) |
O6A—C7A—C8A | 103.3 (2) | O6D—C7D—C8D | 104.2 (2) |
O6A—C7A—H7AA | 111.1 | O6D—C7D—H7DA | 110.9 |
C8A—C7A—H7AA | 111.1 | C8D—C7D—H7DA | 110.9 |
O6A—C7A—H7AB | 111.1 | O6D—C7D—H7DB | 110.9 |
C8A—C7A—H7AB | 111.1 | C8D—C7D—H7DB | 110.9 |
H7AA—C7A—H7AB | 109.1 | H7DA—C7D—H7DB | 108.9 |
N8BA—C8A—N8AA | 106.4 (2) | N8AD—C8D—N8BD | 106.9 (2) |
N8BA—C8A—C7A | 116.5 (2) | N8AD—C8D—C7D | 109.7 (2) |
N8AA—C8A—C7A | 109.0 (2) | N8BD—C8D—C7D | 115.0 (2) |
N8BA—C8A—C1A | 109.2 (2) | N8AD—C8D—C1D | 110.9 (2) |
N8AA—C8A—C1A | 111.5 (2) | N8BD—C8D—C1D | 110.3 (2) |
C7A—C8A—C1A | 104.3 (2) | C7D—C8D—C1D | 104.1 (2) |
O8BA—N8AA—O8AA | 126.5 (3) | O8BD—N8AD—O8AD | 126.9 (2) |
O8BA—N8AA—C8A | 117.4 (2) | O8BD—N8AD—C8D | 115.1 (2) |
O8AA—N8AA—C8A | 116.0 (2) | O8AD—N8AD—C8D | 118.0 (2) |
O8DA—N8BA—O8CA | 126.9 (3) | O8DD—N8BD—O8CD | 126.8 (2) |
O8DA—N8BA—C8A | 115.6 (2) | O8DD—N8BD—C8D | 115.4 (2) |
O8CA—N8BA—C8A | 117.4 (2) | O8CD—N8BD—C8D | 117.7 (2) |
O2B—C1B—C8B | 108.9 (2) | O2E—C1E—C5E | 107.8 (2) |
O2B—C1B—C5B | 108.3 (2) | O2E—C1E—C8E | 113.2 (2) |
C8B—C1B—C5B | 102.6 (2) | C5E—C1E—C8E | 102.0 (2) |
O2B—C1B—H1BA | 112.2 | O2E—C1E—H1EA | 111.1 |
C8B—C1B—H1BA | 112.2 | C5E—C1E—H1EA | 111.1 |
C5B—C1B—H1BA | 112.2 | C8E—C1E—H1EA | 111.1 |
C1B—O2B—C3B | 110.93 (19) | C1E—O2E—C3E | 109.79 (19) |
O2B—C3B—C4B | 103.8 (2) | O2E—C3E—C4E | 102.9 (2) |
O2B—C3B—H3BA | 111.0 | O2E—C3E—H3EA | 111.2 |
C4B—C3B—H3BA | 111.0 | C4E—C3E—H3EA | 111.2 |
O2B—C3B—H3BB | 111.0 | O2E—C3E—H3EB | 111.2 |
C4B—C3B—H3BB | 111.0 | C4E—C3E—H3EB | 111.2 |
H3BA—C3B—H3BB | 109.0 | H3EA—C3E—H3EB | 109.1 |
N4AB—C4B—N4BB | 106.1 (2) | N4AE—C4E—N4BE | 106.4 (2) |
N4AB—C4B—C3B | 114.0 (2) | N4AE—C4E—C5E | 110.9 (2) |
N4BB—C4B—C3B | 110.1 (2) | N4BE—C4E—C5E | 110.3 (2) |
N4AB—C4B—C5B | 113.1 (2) | N4AE—C4E—C3E | 114.7 (2) |
N4BB—C4B—C5B | 109.0 (2) | N4BE—C4E—C3E | 110.8 (2) |
C3B—C4B—C5B | 104.5 (2) | C5E—C4E—C3E | 103.9 (2) |
O4BB—N4AB—O4AB | 126.9 (2) | O4AE—N4AE—O4BE | 126.7 (2) |
O4BB—N4AB—C4B | 116.1 (2) | O4AE—N4AE—C4E | 118.4 (2) |
O4AB—N4AB—C4B | 116.9 (2) | O4BE—N4AE—C4E | 114.9 (2) |
O4DB—N4BB—O4CB | 127.4 (3) | O4DE—N4BE—O4CE | 125.9 (3) |
O4DB—N4BB—C4B | 114.2 (2) | O4DE—N4BE—C4E | 117.2 (2) |
O4CB—N4BB—C4B | 118.3 (2) | O4CE—N4BE—C4E | 116.8 (2) |
O6B—C5B—C1B | 108.0 (2) | O6E—C5E—C4E | 107.0 (2) |
O6B—C5B—C4B | 110.1 (2) | O6E—C5E—C1E | 106.6 (2) |
C1B—C5B—C4B | 102.2 (2) | C4E—C5E—C1E | 102.2 (2) |
O6B—C5B—H5BA | 112.0 | O6E—C5E—H5EA | 113.4 |
C1B—C5B—H5BA | 112.0 | C4E—C5E—H5EA | 113.4 |
C4B—C5B—H5BA | 112.0 | C1E—C5E—H5EA | 113.4 |
C5B—O6B—C7B | 111.0 (2) | C5E—O6E—C7E | 106.46 (19) |
O6B—C7B—C8B | 104.7 (2) | O6E—C7E—C8E | 103.9 (2) |
O6B—C7B—H7BA | 110.8 | O6E—C7E—H7EA | 111.0 |
C8B—C7B—H7BA | 110.8 | C8E—C7E—H7EA | 111.0 |
O6B—C7B—H7BB | 110.8 | O6E—C7E—H7EB | 111.0 |
C8B—C7B—H7BB | 110.8 | C8E—C7E—H7EB | 111.0 |
H7BA—C7B—H7BB | 108.9 | H7EA—C7E—H7EB | 109.0 |
N8AB—C8B—N8BB | 106.5 (2) | N8AE—C8E—N8BE | 105.5 (2) |
N8AB—C8B—C7B | 109.6 (2) | N8AE—C8E—C7E | 110.4 (2) |
N8BB—C8B—C7B | 115.1 (2) | N8BE—C8E—C7E | 112.2 (2) |
N8AB—C8B—C1B | 111.1 (2) | N8AE—C8E—C1E | 112.6 (2) |
N8BB—C8B—C1B | 110.1 (2) | N8BE—C8E—C1E | 111.1 (2) |
C7B—C8B—C1B | 104.5 (2) | C7E—C8E—C1E | 105.2 (2) |
O8AB—N8AB—O8BB | 126.8 (2) | O8AE—N8AE—O8BE | 126.0 (3) |
O8AB—N8AB—C8B | 114.6 (2) | O8AE—N8AE—C8E | 119.0 (2) |
O8BB—N8AB—C8B | 118.5 (2) | O8BE—N8AE—C8E | 115.0 (2) |
O8DB—N8BB—O8CB | 126.6 (2) | O8CE—N8BE—O8DE | 127.2 (3) |
O8DB—N8BB—C8B | 115.5 (2) | O8CE—N8BE—C8E | 118.3 (2) |
O8CB—N8BB—C8B | 117.8 (2) | O8DE—N8BE—C8E | 114.4 (2) |
Experimental details
Crystal data | |
Chemical formula | C6H6N4O10 |
Mr | 294.15 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 93 |
a, b, c (Å) | 9.5746 (9), 11.347 (1), 29.241 (3) |
β (°) | 92.546 (2) |
V (Å3) | 3173.8 (5) |
Z | 12 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.45 × 0.22 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD area-detector diffractometer |
Absorption correction | Integration (SHELXTL; Bruker 2001) |
Tmin, Tmax | 0.922, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25608, 13028, 10983 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.130, 0.89 |
No. of reflections | 13028 |
No. of parameters | 1081 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
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.