Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803007499/bt6263sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803007499/bt6263Isup2.hkl |
CCDC reference: 214629
Key indicators
- Single-crystal X-ray study
- T = 133 K
- Mean (C-C) = 0.002 Å
- R factor = 0.034
- wR factor = 0.079
- Data-to-parameter ratio = 13.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Triphosgene (bis(trichloromethyl) carbonate) was treated with six equivalents of p-nitrophenol and six equivalents of triethylamine in dichloromethane and recrystallized from benzene (Simon et al., 2001).
Hydrogen atoms were included using a riding model, with fixed C—H bond lengths of 0.95 Å; U(H) values were fixed at 1.2 times the U(eq) of the parent atom.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.
Fig. 1. The asymmetric unit of the title compound in the crystal. Ellipsoids represent 50% probability levels; H atom radii are arbitrary. |
C13H8N2O7·1/3C6H6 | F(000) = 2040 |
Mr = 330.25 | Dx = 1.531 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 21.074 (2) Å | Cell parameters from 6133 reflections |
b = 8.4949 (8) Å | θ = 2.5–26.4° |
c = 25.828 (2) Å | µ = 0.12 mm−1 |
β = 111.618 (5)° | T = 133 K |
V = 4298.6 (7) Å3 | Prism, colourless |
Z = 12 | 0.40 × 0.25 × 0.15 mm |
Bruker SMART 1000 CCD diffractometer | 5569 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.048 |
Graphite monochromator | θmax = 26.4°, θmin = 1.6° |
Detector resolution: 8.192 pixels mm-1 | h = −26→18 |
ω–scan | k = −10→10 |
26129 measured reflections | l = −31→32 |
8781 independent reflections |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0333P)2] where P = (Fo2 + 2Fc2)/3 |
8781 reflections | (Δ/σ)max < 0.001 |
649 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C13H8N2O7·1/3C6H6 | V = 4298.6 (7) Å3 |
Mr = 330.25 | Z = 12 |
Monoclinic, P21/c | Mo Kα radiation |
a = 21.074 (2) Å | µ = 0.12 mm−1 |
b = 8.4949 (8) Å | T = 133 K |
c = 25.828 (2) Å | 0.40 × 0.25 × 0.15 mm |
β = 111.618 (5)° |
Bruker SMART 1000 CCD diffractometer | 5569 reflections with I > 2σ(I) |
26129 measured reflections | Rint = 0.048 |
8781 independent reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 0.92 | Δρmax = 0.24 e Å−3 |
8781 reflections | Δρmin = −0.21 e Å−3 |
649 parameters |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 15.0917 (0.0098) x + 5.5125 (0.0043) y − 0.6415 (0.0167) z = 1.0199 (0.0022) * −0.0062 (0.0011) C11 * 0.0086 (0.0011) C12 * −0.0031 (0.0011) C13 * −0.0049 (0.0011) C14 * 0.0072 (0.0011) C15 * −0.0017 (0.0011) C16 Rms deviation of fitted atoms = 0.0058 − 21.0139 (0.0023) x + 0.5765 (0.0063) y + 8.6857 (0.0197) z = 1.5257 (0.0037) Angle to previous plane (with approximate e.s.d.) = 47.26 (0.05) * 0.0032 (0.0014) C1 * −0.0013 (0.0006) O1 * −0.0009 (0.0004) O2 * −0.0009 (0.0004) O3 0.0180 (0.0026) C11 − 0.0096 (0.0027) C21 Rms deviation of fitted atoms = 0.0018 − 11.2215 (0.0120) x − 7.0549 (0.0032) y + 8.9956 (0.0161) z = 0.2280 (0.0055) Angle to previous plane (with approximate e.s.d.) = 62.02 (0.05) * −0.0039 (0.0012) C21 * 0.0012 (0.0012) C22 * 0.0024 (0.0011) C23 * −0.0034 (0.0011) C24 * 0.0008 (0.0011) C25 * 0.0029 (0.0011) C26 Rms deviation of fitted atoms = 0.0027 11.5111 (0.0113) x + 6.2091 (0.0038) y + 4.6268 (0.0157) z = 5.5388 (0.0028) Angle to previous plane (with approximate e.s.d.) = 33.81 (0.06) * 0.0044 (0.0011) C11' * −0.0007 (0.0011) C12' * −0.0022 (0.0011) C13' * 0.0014 (0.0011) C14' * 0.0023 (0.0011) C15' * −0.0052 (0.0011) C16' Rms deviation of fitted atoms = 0.0031 15.1122 (0.0102) x − 1.2489 (0.0055) y + 9.5354 (0.0166) z = 6.3367 (0.0024) Angle to previous plane (with approximate e.s.d.) = 55.74 (0.06) * −0.0058 (0.0012) C1' * 0.0024 (0.0005) O1' * 0.0017 (0.0004) O2' * 0.0017 (0.0004) O3' −0.1276 (0.0023) C11' −0.2889 (0.0023) C21' Rms deviation of fitted atoms = 0.0034 15.3857 (0.0097) x + 5.7806 (0.0042) y − 8.4561 (0.0163) z = 3.5730 (0.0053) Angle to previous plane (with approximate e.s.d.) = 67.62 (0.05) * 0.0028 (0.0012) C21' * −0.0102 (0.0012) C22' * 0.0085 (0.0012) C23' * 0.0006 (0.0011) C24' * −0.0080 (0.0011) C25' * 0.0064 (0.0011) C26' Rms deviation of fitted atoms = 0.0069 15.0568 (0.0098) x − 5.3739 (0.0044) y + 0.3788 (0.0163) z = 0.0345 (0.0099) Angle to previous plane (with approximate e.s.d.) = 85.85 (0.04) * −0.0082 (0.0011) C11" * 0.0006 (0.0011) C12" * 0.0077 (0.0011) C13" * −0.0083 (0.0011) C14" * 0.0007 (0.0011) C15" * 0.0075 (0.0011) C16" Rms deviation of fitted atoms = 0.0065 15.1477 (0.0111) x + 0.9976 (0.0057) y + 9.6144 (0.0183) z = 10.2386 (0.0068) Angle to previous plane (with approximate e.s.d.) = 49.90 (0.06) * −0.0004 (0.0013) C1" * 0.0002 (0.0005) O1" * 0.0001 (0.0004) O2" * 0.0001 (0.0004) O3" −0.1406 (0.0025) C11" −0.0667 (0.0025) C21" Rms deviation of fitted atoms = 0.0002 11.7575 (0.0125) x + 6.5674 (0.0039) y + 1.9368 (0.0177) z = 10.4644 (0.0046) Angle to previous plane (with approximate e.s.d.) = 45.69 (0.07) * −0.0056 (0.0012) C21" * 0.0063 (0.0012) C22" * −0.0017 (0.0012) C23" * −0.0036 (0.0012) C24" * 0.0044 (0.0012) C25" * 0.0003 (0.0012) C26" Rms deviation of fitted atoms = 0.0042 ============================================================================= Short contacts: 2.9230 (0.0017) O1 - O5_$2 3.0936 (0.0020) C23 - O3_$1 3.1182 (0.0019) C14" - O2'_$5 2.9838 (0.0016) O1" - O6' 2.9746 (0.0020) C1" - O6' 2.9502 (0.0021) C1 - O7'_$7 2.9348 (0.0018) N1' - O1"_$3 2.9966 (0.0019) C14' - O1"_$3 Operators for generating equivalent atoms: $1 − x, y + 1/2, −z + 1/2 $2 − x, −y + 1, −z $3 x, −y + 1/2, z − 1/2 $5 x, −y + 1/2, z + 1/2 $7 − x, y − 1/2, −z + 1/2 |
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 | ||
O1 | 0.01126 (6) | 0.43743 (14) | 0.17370 (4) | 0.0320 (3) | |
O2 | −0.01704 (6) | 0.21654 (13) | 0.11996 (4) | 0.0320 (3) | |
O3 | 0.01845 (6) | 0.18862 (13) | 0.20765 (4) | 0.0350 (3) | |
O4 | −0.14343 (6) | 0.58296 (16) | −0.10593 (5) | 0.0436 (3) | |
O5 | −0.09830 (6) | 0.37969 (16) | −0.13037 (5) | 0.0385 (3) | |
O6 | 0.17613 (6) | 0.28928 (16) | 0.46195 (5) | 0.0430 (3) | |
O7 | 0.08190 (6) | 0.40695 (14) | 0.45328 (4) | 0.0347 (3) | |
N1 | −0.10969 (7) | 0.46043 (18) | −0.09516 (6) | 0.0313 (4) | |
N2 | 0.11840 (7) | 0.33479 (16) | 0.43380 (5) | 0.0280 (3) | |
C1 | 0.00484 (8) | 0.2997 (2) | 0.16784 (6) | 0.0258 (4) | |
C11 | −0.03708 (8) | 0.2934 (2) | 0.06854 (6) | 0.0258 (4) | |
C12 | −0.01313 (8) | 0.2261 (2) | 0.03039 (6) | 0.0275 (4) | |
H12 | 0.0190 | 0.1425 | 0.0412 | 0.033* | |
C13 | −0.03681 (8) | 0.2825 (2) | −0.02362 (6) | 0.0282 (4) | |
H13 | −0.0219 | 0.2372 | −0.0508 | 0.034* | |
C14 | −0.08247 (8) | 0.4056 (2) | −0.03718 (6) | 0.0250 (4) | |
C15 | −0.10567 (8) | 0.47574 (19) | 0.00097 (7) | 0.0277 (4) | |
H15 | −0.1366 | 0.5618 | −0.0096 | 0.033* | |
C16 | −0.08270 (8) | 0.4175 (2) | 0.05493 (7) | 0.0285 (4) | |
H16 | −0.0980 | 0.4621 | 0.0820 | 0.034* | |
C21 | 0.04328 (9) | 0.23554 (19) | 0.26363 (6) | 0.0264 (4) | |
C22 | 0.00376 (9) | 0.32455 (19) | 0.28470 (6) | 0.0282 (4) | |
H22 | −0.0396 | 0.3628 | 0.2609 | 0.034* | |
C23 | 0.02836 (8) | 0.35728 (19) | 0.34119 (6) | 0.0245 (4) | |
H23 | 0.0024 | 0.4182 | 0.3571 | 0.029* | |
C24 | 0.09143 (8) | 0.29926 (19) | 0.37372 (6) | 0.0227 (4) | |
C25 | 0.13096 (8) | 0.20884 (19) | 0.35259 (7) | 0.0274 (4) | |
H25 | 0.1742 | 0.1702 | 0.3763 | 0.033* | |
C26 | 0.10633 (8) | 0.17610 (19) | 0.29641 (7) | 0.0282 (4) | |
H26 | 0.1321 | 0.1141 | 0.2806 | 0.034* | |
O1' | 0.31915 (6) | 0.41828 (13) | 0.21378 (4) | 0.0290 (3) | |
O2' | 0.30928 (5) | 0.15569 (13) | 0.19496 (4) | 0.0270 (3) | |
O3' | 0.27625 (5) | 0.24280 (13) | 0.25871 (4) | 0.0267 (3) | |
O4' | 0.35203 (6) | 0.23626 (15) | −0.03075 (5) | 0.0401 (3) | |
O5' | 0.43904 (6) | 0.08886 (15) | 0.01379 (5) | 0.0374 (3) | |
O6' | 0.17954 (6) | 0.67527 (16) | 0.40989 (5) | 0.0455 (4) | |
O7' | 0.13530 (6) | 0.80252 (15) | 0.33249 (5) | 0.0375 (3) | |
N1' | 0.38770 (7) | 0.16378 (17) | 0.01101 (6) | 0.0284 (3) | |
N2' | 0.16889 (7) | 0.69312 (17) | 0.36028 (6) | 0.0296 (3) | |
C1' | 0.30326 (8) | 0.2885 (2) | 0.22110 (6) | 0.0238 (4) | |
C11' | 0.33048 (8) | 0.16869 (19) | 0.14950 (6) | 0.0229 (4) | |
C12' | 0.38290 (8) | 0.07014 (19) | 0.15021 (6) | 0.0259 (4) | |
H12' | 0.4054 | 0.0048 | 0.1815 | 0.031* | |
C13' | 0.40208 (8) | 0.06863 (19) | 0.10421 (6) | 0.0256 (4) | |
H13' | 0.4379 | 0.0023 | 0.1033 | 0.031* | |
C14' | 0.36786 (8) | 0.16573 (19) | 0.05981 (6) | 0.0234 (4) | |
C15' | 0.31525 (8) | 0.26386 (19) | 0.05919 (6) | 0.0252 (4) | |
H15' | 0.2928 | 0.3296 | 0.0280 | 0.030* | |
C16' | 0.29595 (8) | 0.26447 (19) | 0.10479 (6) | 0.0255 (4) | |
H16' | 0.2596 | 0.3296 | 0.1054 | 0.031* | |
C21' | 0.25144 (8) | 0.36392 (19) | 0.28341 (6) | 0.0233 (4) | |
C22' | 0.19810 (8) | 0.4556 (2) | 0.25056 (6) | 0.0273 (4) | |
H22' | 0.1800 | 0.4426 | 0.2113 | 0.033* | |
C23' | 0.17120 (8) | 0.5671 (2) | 0.27566 (6) | 0.0265 (4) | |
H23' | 0.1352 | 0.6344 | 0.2540 | 0.032* | |
C24' | 0.19815 (8) | 0.57807 (19) | 0.33311 (6) | 0.0231 (4) | |
C25' | 0.25104 (8) | 0.48442 (19) | 0.36632 (6) | 0.0247 (4) | |
H25' | 0.2680 | 0.4943 | 0.4057 | 0.030* | |
C26' | 0.27879 (8) | 0.37550 (19) | 0.34066 (6) | 0.0245 (4) | |
H26' | 0.3158 | 0.3104 | 0.3621 | 0.029* | |
O1" | 0.31636 (6) | 0.63824 (14) | 0.50029 (4) | 0.0301 (3) | |
O2" | 0.27915 (6) | 0.84461 (13) | 0.53749 (5) | 0.0320 (3) | |
O3" | 0.31697 (6) | 0.89297 (14) | 0.47288 (5) | 0.0353 (3) | |
O4" | 0.18185 (6) | 0.57290 (15) | 0.72046 (5) | 0.0412 (3) | |
O5" | 0.12995 (8) | 0.41327 (19) | 0.65337 (6) | 0.0663 (5) | |
O6" | 0.45710 (7) | 0.67693 (18) | 0.30858 (5) | 0.0516 (4) | |
O7" | 0.38378 (6) | 0.84417 (17) | 0.25708 (5) | 0.0465 (4) | |
N1" | 0.16855 (7) | 0.52355 (18) | 0.67289 (6) | 0.0349 (4) | |
N2" | 0.41070 (7) | 0.77117 (19) | 0.30076 (6) | 0.0346 (4) | |
C1" | 0.30549 (8) | 0.7740 (2) | 0.50326 (6) | 0.0268 (4) | |
C11" | 0.25493 (8) | 0.74961 (19) | 0.57088 (6) | 0.0253 (4) | |
C12" | 0.21139 (8) | 0.62449 (19) | 0.54934 (7) | 0.0263 (4) | |
H12" | 0.2006 | 0.5915 | 0.5119 | 0.032* | |
C13" | 0.18381 (8) | 0.5483 (2) | 0.58343 (6) | 0.0275 (4) | |
H13" | 0.1541 | 0.4611 | 0.5699 | 0.033* | |
C14" | 0.20021 (8) | 0.6010 (2) | 0.63766 (6) | 0.0252 (4) | |
C15" | 0.24444 (8) | 0.7248 (2) | 0.65927 (6) | 0.0273 (4) | |
H15" | 0.2554 | 0.7577 | 0.6967 | 0.033* | |
C16" | 0.27246 (8) | 0.7997 (2) | 0.62543 (7) | 0.0271 (4) | |
H16" | 0.3034 | 0.8846 | 0.6393 | 0.033* | |
C21" | 0.34171 (9) | 0.8537 (2) | 0.43104 (7) | 0.0287 (4) | |
C22" | 0.39658 (8) | 0.7546 (2) | 0.44003 (7) | 0.0304 (4) | |
H22" | 0.4188 | 0.7065 | 0.4753 | 0.036* | |
C23" | 0.41870 (8) | 0.7266 (2) | 0.39659 (7) | 0.0294 (4) | |
H23" | 0.4560 | 0.6578 | 0.4014 | 0.035* | |
C24" | 0.38581 (8) | 0.8000 (2) | 0.34625 (6) | 0.0277 (4) | |
C25" | 0.33165 (8) | 0.9009 (2) | 0.33709 (7) | 0.0321 (4) | |
H25" | 0.3103 | 0.9508 | 0.3020 | 0.038* | |
C26" | 0.30923 (9) | 0.9276 (2) | 0.38034 (7) | 0.0336 (4) | |
H26" | 0.2718 | 0.9963 | 0.3753 | 0.040* | |
C101 | 0.54435 (10) | 0.7894 (3) | 0.15648 (10) | 0.0505 (6) | |
H101 | 0.5751 | 0.8759 | 0.1655 | 0.061* | |
C102 | 0.52781 (11) | 0.7168 (3) | 0.10570 (9) | 0.0599 (7) | |
H102 | 0.5467 | 0.7525 | 0.0796 | 0.072* | |
C103 | 0.48244 (12) | 0.5885 (3) | 0.09310 (8) | 0.0622 (7) | |
H103 | 0.4701 | 0.5358 | 0.0583 | 0.075* | |
C104 | 0.45609 (10) | 0.5406 (3) | 0.13232 (9) | 0.0529 (6) | |
H104 | 0.4254 | 0.4541 | 0.1246 | 0.063* | |
C105 | 0.47393 (10) | 0.6171 (3) | 0.18192 (8) | 0.0481 (5) | |
H105 | 0.4554 | 0.5836 | 0.2085 | 0.058* | |
C106 | 0.51753 (10) | 0.7397 (3) | 0.19376 (8) | 0.0468 (5) | |
H106 | 0.5295 | 0.7916 | 0.2286 | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0418 (7) | 0.0239 (7) | 0.0275 (6) | −0.0076 (5) | 0.0096 (5) | 0.0001 (5) |
O2 | 0.0524 (8) | 0.0235 (7) | 0.0180 (6) | 0.0016 (6) | 0.0104 (5) | 0.0005 (5) |
O3 | 0.0619 (8) | 0.0221 (7) | 0.0187 (6) | 0.0002 (6) | 0.0121 (6) | 0.0000 (5) |
O4 | 0.0458 (8) | 0.0417 (9) | 0.0338 (7) | 0.0040 (7) | 0.0035 (6) | 0.0119 (6) |
O5 | 0.0380 (8) | 0.0548 (9) | 0.0237 (6) | −0.0049 (6) | 0.0126 (6) | 0.0011 (6) |
O6 | 0.0341 (8) | 0.0526 (9) | 0.0294 (7) | 0.0066 (6) | −0.0034 (6) | 0.0007 (6) |
O7 | 0.0400 (7) | 0.0396 (8) | 0.0254 (6) | −0.0012 (6) | 0.0131 (6) | −0.0061 (6) |
N1 | 0.0247 (8) | 0.0380 (10) | 0.0266 (8) | −0.0071 (7) | 0.0041 (6) | 0.0061 (7) |
N2 | 0.0310 (9) | 0.0246 (8) | 0.0254 (8) | −0.0051 (7) | 0.0067 (7) | 0.0003 (6) |
C1 | 0.0305 (10) | 0.0254 (10) | 0.0220 (9) | −0.0013 (8) | 0.0104 (7) | 0.0012 (7) |
C11 | 0.0309 (10) | 0.0250 (10) | 0.0203 (8) | −0.0047 (7) | 0.0079 (7) | 0.0024 (7) |
C12 | 0.0267 (10) | 0.0295 (10) | 0.0252 (9) | 0.0013 (7) | 0.0084 (7) | 0.0015 (7) |
C13 | 0.0255 (9) | 0.0351 (11) | 0.0244 (9) | −0.0032 (8) | 0.0096 (7) | −0.0012 (8) |
C14 | 0.0225 (9) | 0.0298 (10) | 0.0198 (8) | −0.0082 (7) | 0.0043 (7) | 0.0042 (7) |
C15 | 0.0284 (10) | 0.0223 (9) | 0.0291 (9) | −0.0019 (7) | 0.0068 (7) | 0.0027 (7) |
C16 | 0.0350 (10) | 0.0255 (10) | 0.0274 (9) | −0.0025 (8) | 0.0142 (8) | −0.0033 (7) |
C21 | 0.0400 (10) | 0.0190 (9) | 0.0193 (8) | −0.0043 (8) | 0.0100 (7) | −0.0001 (7) |
C22 | 0.0317 (10) | 0.0242 (10) | 0.0231 (9) | 0.0011 (8) | 0.0038 (7) | 0.0005 (7) |
C23 | 0.0291 (10) | 0.0207 (9) | 0.0250 (9) | −0.0005 (7) | 0.0114 (7) | −0.0025 (7) |
C24 | 0.0256 (9) | 0.0216 (9) | 0.0195 (8) | −0.0056 (7) | 0.0067 (7) | 0.0006 (7) |
C25 | 0.0264 (9) | 0.0259 (10) | 0.0294 (9) | 0.0001 (7) | 0.0097 (7) | 0.0043 (8) |
C26 | 0.0362 (11) | 0.0218 (10) | 0.0311 (10) | 0.0005 (8) | 0.0177 (8) | 0.0005 (7) |
O1' | 0.0407 (7) | 0.0232 (7) | 0.0267 (6) | −0.0017 (5) | 0.0165 (5) | 0.0006 (5) |
O2' | 0.0389 (7) | 0.0216 (7) | 0.0269 (6) | 0.0004 (5) | 0.0195 (5) | −0.0010 (5) |
O3' | 0.0385 (7) | 0.0229 (7) | 0.0238 (6) | 0.0036 (5) | 0.0173 (5) | 0.0026 (5) |
O4' | 0.0529 (8) | 0.0459 (8) | 0.0222 (6) | 0.0020 (7) | 0.0146 (6) | 0.0027 (6) |
O5' | 0.0311 (7) | 0.0510 (9) | 0.0353 (7) | −0.0024 (6) | 0.0184 (6) | −0.0068 (6) |
O6' | 0.0547 (9) | 0.0611 (10) | 0.0214 (7) | 0.0259 (7) | 0.0149 (6) | 0.0018 (6) |
O7' | 0.0447 (8) | 0.0331 (8) | 0.0351 (7) | 0.0173 (6) | 0.0150 (6) | 0.0072 (6) |
N1' | 0.0315 (9) | 0.0306 (9) | 0.0239 (8) | −0.0102 (7) | 0.0111 (7) | −0.0071 (7) |
N2' | 0.0279 (8) | 0.0328 (9) | 0.0267 (8) | 0.0066 (7) | 0.0082 (6) | 0.0011 (7) |
C1' | 0.0261 (9) | 0.0240 (10) | 0.0204 (8) | 0.0028 (7) | 0.0074 (7) | 0.0010 (7) |
C11' | 0.0265 (9) | 0.0225 (9) | 0.0217 (8) | −0.0044 (7) | 0.0112 (7) | −0.0032 (7) |
C12' | 0.0280 (10) | 0.0257 (10) | 0.0229 (9) | 0.0016 (7) | 0.0080 (7) | 0.0018 (7) |
C13' | 0.0229 (9) | 0.0276 (10) | 0.0266 (9) | −0.0008 (7) | 0.0096 (7) | −0.0037 (7) |
C14' | 0.0264 (9) | 0.0259 (10) | 0.0181 (8) | −0.0071 (7) | 0.0085 (7) | −0.0055 (7) |
C15' | 0.0274 (9) | 0.0249 (10) | 0.0196 (8) | −0.0031 (7) | 0.0044 (7) | 0.0002 (7) |
C16' | 0.0252 (9) | 0.0244 (10) | 0.0262 (9) | 0.0009 (7) | 0.0089 (7) | −0.0025 (7) |
C21' | 0.0288 (9) | 0.0211 (9) | 0.0234 (9) | 0.0004 (7) | 0.0136 (7) | 0.0000 (7) |
C22' | 0.0327 (10) | 0.0315 (10) | 0.0164 (8) | 0.0026 (8) | 0.0075 (7) | 0.0018 (7) |
C23' | 0.0263 (9) | 0.0274 (10) | 0.0231 (9) | 0.0048 (7) | 0.0061 (7) | 0.0053 (7) |
C24' | 0.0257 (9) | 0.0223 (9) | 0.0230 (8) | 0.0024 (7) | 0.0109 (7) | 0.0003 (7) |
C25' | 0.0249 (9) | 0.0293 (10) | 0.0186 (8) | 0.0001 (7) | 0.0065 (7) | 0.0006 (7) |
C26' | 0.0233 (9) | 0.0266 (10) | 0.0234 (9) | 0.0028 (7) | 0.0083 (7) | 0.0041 (7) |
O1" | 0.0382 (7) | 0.0232 (7) | 0.0322 (7) | 0.0054 (5) | 0.0168 (5) | 0.0023 (5) |
O2" | 0.0466 (8) | 0.0241 (7) | 0.0322 (7) | −0.0017 (6) | 0.0226 (6) | −0.0017 (5) |
O3" | 0.0540 (8) | 0.0245 (7) | 0.0375 (7) | 0.0018 (6) | 0.0287 (6) | 0.0033 (5) |
O4" | 0.0574 (9) | 0.0433 (8) | 0.0301 (7) | −0.0020 (6) | 0.0246 (6) | −0.0028 (6) |
O5" | 0.0847 (12) | 0.0687 (11) | 0.0602 (10) | −0.0484 (9) | 0.0439 (8) | −0.0243 (8) |
O6" | 0.0512 (9) | 0.0710 (11) | 0.0388 (8) | 0.0287 (8) | 0.0241 (7) | 0.0130 (7) |
O7" | 0.0479 (8) | 0.0647 (10) | 0.0279 (7) | 0.0105 (7) | 0.0152 (6) | 0.0171 (7) |
N1" | 0.0399 (9) | 0.0343 (10) | 0.0353 (9) | −0.0014 (7) | 0.0194 (7) | −0.0016 (7) |
N2" | 0.0317 (9) | 0.0447 (10) | 0.0269 (8) | 0.0014 (8) | 0.0100 (7) | 0.0050 (7) |
C1" | 0.0314 (10) | 0.0262 (11) | 0.0242 (9) | 0.0004 (8) | 0.0118 (7) | 0.0009 (7) |
C11" | 0.0286 (10) | 0.0224 (9) | 0.0272 (9) | 0.0028 (7) | 0.0132 (7) | 0.0032 (7) |
C12" | 0.0291 (10) | 0.0278 (10) | 0.0210 (8) | 0.0016 (7) | 0.0080 (7) | −0.0030 (7) |
C13" | 0.0265 (10) | 0.0251 (10) | 0.0300 (9) | −0.0008 (7) | 0.0095 (7) | −0.0029 (7) |
C14" | 0.0255 (9) | 0.0258 (10) | 0.0261 (9) | 0.0037 (7) | 0.0117 (7) | 0.0017 (7) |
C15" | 0.0287 (10) | 0.0294 (10) | 0.0226 (9) | 0.0034 (8) | 0.0082 (7) | −0.0035 (7) |
C16" | 0.0287 (10) | 0.0242 (10) | 0.0280 (9) | −0.0006 (7) | 0.0100 (7) | −0.0043 (7) |
C21" | 0.0360 (10) | 0.0241 (10) | 0.0301 (10) | −0.0031 (8) | 0.0171 (8) | 0.0008 (7) |
C22" | 0.0319 (10) | 0.0335 (11) | 0.0241 (9) | 0.0008 (8) | 0.0085 (7) | 0.0063 (8) |
C23" | 0.0245 (9) | 0.0342 (11) | 0.0284 (9) | 0.0044 (8) | 0.0086 (7) | 0.0060 (8) |
C24" | 0.0275 (10) | 0.0319 (11) | 0.0241 (9) | −0.0019 (8) | 0.0099 (7) | 0.0039 (8) |
C25" | 0.0336 (11) | 0.0326 (11) | 0.0280 (9) | 0.0040 (8) | 0.0091 (8) | 0.0104 (8) |
C26" | 0.0372 (11) | 0.0270 (10) | 0.0398 (11) | 0.0070 (8) | 0.0180 (9) | 0.0085 (8) |
C101 | 0.0327 (12) | 0.0405 (13) | 0.0730 (16) | 0.0020 (9) | 0.0133 (11) | 0.0090 (11) |
C102 | 0.0440 (14) | 0.088 (2) | 0.0604 (15) | 0.0294 (13) | 0.0336 (12) | 0.0364 (14) |
C103 | 0.0566 (15) | 0.086 (2) | 0.0345 (12) | 0.0293 (14) | 0.0051 (11) | −0.0169 (12) |
C104 | 0.0413 (13) | 0.0463 (14) | 0.0660 (15) | −0.0086 (10) | 0.0139 (11) | −0.0146 (12) |
C105 | 0.0501 (13) | 0.0504 (14) | 0.0496 (13) | 0.0012 (11) | 0.0250 (10) | 0.0032 (11) |
C106 | 0.0404 (12) | 0.0475 (14) | 0.0451 (12) | 0.0060 (10) | 0.0072 (10) | −0.0069 (10) |
O1—C1 | 1.1809 (19) | C21'—C26' | 1.379 (2) |
O2—C1 | 1.3494 (19) | C22'—C23' | 1.382 (2) |
O2—C11 | 1.3981 (18) | C22'—H22' | 0.9500 |
O3—C1 | 1.3466 (19) | C23'—C24' | 1.383 (2) |
O3—C21 | 1.4019 (18) | C23'—H23' | 0.9500 |
O4—N1 | 1.2332 (18) | C24'—C25' | 1.381 (2) |
O5—N1 | 1.2311 (18) | C25'—C26' | 1.387 (2) |
O6—N2 | 1.2275 (16) | C25'—H25' | 0.9500 |
O7—N2 | 1.2271 (17) | C26'—H26' | 0.9500 |
N1—C14 | 1.468 (2) | O1"—C1" | 1.1839 (19) |
N2—C24 | 1.4738 (19) | O2"—C1" | 1.3458 (19) |
C11—C16 | 1.382 (2) | O2"—C11" | 1.4070 (19) |
C11—C12 | 1.385 (2) | O3"—C1" | 1.355 (2) |
C12—C13 | 1.383 (2) | O3"—C21" | 1.4024 (19) |
C12—H12 | 0.9500 | O4"—N1" | 1.2288 (17) |
C13—C14 | 1.376 (2) | O5"—N1" | 1.2212 (18) |
C13—H13 | 0.9500 | O6"—N2" | 1.2216 (18) |
C14—C15 | 1.386 (2) | O7"—N2" | 1.2279 (17) |
C15—C16 | 1.387 (2) | N1"—C14" | 1.468 (2) |
C15—H15 | 0.9500 | N2"—C24" | 1.473 (2) |
C16—H16 | 0.9500 | C11"—C12" | 1.380 (2) |
C21—C22 | 1.377 (2) | C11"—C16" | 1.385 (2) |
C21—C26 | 1.381 (2) | C12"—C13" | 1.382 (2) |
C22—C23 | 1.385 (2) | C12"—H12" | 0.9500 |
C22—H22 | 0.9500 | C13"—C14" | 1.387 (2) |
C23—C24 | 1.376 (2) | C13"—H13" | 0.9500 |
C23—H23 | 0.9500 | C14"—C15" | 1.380 (2) |
C24—C25 | 1.385 (2) | C15"—C16" | 1.377 (2) |
C25—C26 | 1.377 (2) | C15"—H15" | 0.9500 |
C25—H25 | 0.9500 | C16"—H16" | 0.9500 |
C26—H26 | 0.9500 | C21"—C22" | 1.379 (2) |
O1'—C1' | 1.1872 (19) | C21"—C26" | 1.385 (2) |
O2'—C1' | 1.3448 (19) | C22"—C23" | 1.385 (2) |
O2'—C11' | 1.4061 (18) | C22"—H22" | 0.9500 |
O3'—C1' | 1.3514 (19) | C23"—C24" | 1.377 (2) |
O3'—C21' | 1.4087 (18) | C23"—H23" | 0.9500 |
O4'—N1' | 1.2288 (17) | C24"—C25" | 1.376 (2) |
O5'—N1' | 1.2344 (17) | C25"—C26" | 1.383 (2) |
O6'—N2' | 1.2263 (16) | C25"—H25" | 0.9500 |
O7'—N2' | 1.2269 (16) | C26"—H26" | 0.9500 |
N1'—C14' | 1.467 (2) | C101—C106 | 1.351 (3) |
N2'—C24' | 1.465 (2) | C101—C102 | 1.373 (3) |
C11'—C16' | 1.381 (2) | C101—H101 | 0.9500 |
C11'—C12' | 1.381 (2) | C102—C103 | 1.407 (3) |
C12'—C13' | 1.389 (2) | C102—H102 | 0.9500 |
C12'—H12' | 0.9500 | C103—C104 | 1.384 (3) |
C13'—C14' | 1.381 (2) | C103—H103 | 0.9500 |
C13'—H13' | 0.9500 | C104—C105 | 1.360 (3) |
C14'—C15' | 1.382 (2) | C104—H104 | 0.9500 |
C15'—C16' | 1.380 (2) | C105—C106 | 1.347 (3) |
C15'—H15' | 0.9500 | C105—H105 | 0.9500 |
C16'—H16' | 0.9500 | C106—H106 | 0.9500 |
C21'—C22' | 1.374 (2) | ||
C1—O2—C11 | 120.50 (13) | C21'—C22'—H22' | 120.6 |
C1—O3—C21 | 118.81 (13) | C23'—C22'—H22' | 120.6 |
O5—N1—O4 | 123.82 (14) | C22'—C23'—C24' | 118.17 (15) |
O5—N1—C14 | 117.86 (15) | C22'—C23'—H23' | 120.9 |
O4—N1—C14 | 118.31 (15) | C24'—C23'—H23' | 120.9 |
O7—N2—O6 | 123.28 (13) | C25'—C24'—C23' | 123.11 (15) |
O7—N2—C24 | 118.50 (13) | C25'—C24'—N2' | 118.21 (13) |
O6—N2—C24 | 118.22 (14) | C23'—C24'—N2' | 118.68 (14) |
O1—C1—O3 | 127.89 (15) | C24'—C25'—C26' | 118.28 (14) |
O1—C1—O2 | 128.36 (15) | C24'—C25'—H25' | 120.9 |
O3—C1—O2 | 103.74 (14) | C26'—C25'—H25' | 120.9 |
C16—C11—C12 | 122.38 (15) | C21'—C26'—C25' | 118.49 (15) |
C16—C11—O2 | 122.42 (15) | C21'—C26'—H26' | 120.8 |
C12—C11—O2 | 114.91 (15) | C25'—C26'—H26' | 120.8 |
C13—C12—C11 | 118.94 (16) | C1"—O2"—C11" | 118.53 (13) |
C13—C12—H12 | 120.5 | C1"—O3"—C21" | 117.72 (13) |
C11—C12—H12 | 120.5 | O5"—N1"—O4" | 123.12 (15) |
C14—C13—C12 | 118.62 (16) | O5"—N1"—C14" | 118.28 (14) |
C14—C13—H13 | 120.7 | O4"—N1"—C14" | 118.60 (15) |
C12—C13—H13 | 120.7 | O6"—N2"—O7" | 123.62 (15) |
C13—C14—C15 | 122.86 (15) | O6"—N2"—C24" | 118.40 (14) |
C13—C14—N1 | 118.33 (15) | O7"—N2"—C24" | 117.99 (15) |
C15—C14—N1 | 118.76 (16) | O1"—C1"—O2" | 127.82 (16) |
C14—C15—C16 | 118.50 (16) | O1"—C1"—O3" | 127.52 (16) |
C14—C15—H15 | 120.7 | O2"—C1"—O3" | 104.66 (14) |
C16—C15—H15 | 120.7 | C12"—C11"—C16" | 122.34 (15) |
C11—C16—C15 | 118.69 (16) | C12"—C11"—O2" | 122.14 (14) |
C11—C16—H16 | 120.7 | C16"—C11"—O2" | 115.23 (15) |
C15—C16—H16 | 120.7 | C11"—C12"—C13" | 118.50 (15) |
C22—C21—C26 | 122.93 (14) | C11"—C12"—H12" | 120.8 |
C22—C21—O3 | 120.89 (15) | C13"—C12"—H12" | 120.8 |
C26—C21—O3 | 115.95 (15) | C12"—C13"—C14" | 119.02 (16) |
C21—C22—C23 | 118.72 (15) | C12"—C13"—H13" | 120.5 |
C21—C22—H22 | 120.6 | C14"—C13"—H13" | 120.5 |
C23—C22—H22 | 120.6 | C15"—C14"—C13" | 122.31 (16) |
C24—C23—C22 | 118.29 (15) | C15"—C14"—N1" | 119.00 (15) |
C24—C23—H23 | 120.9 | C13"—C14"—N1" | 118.69 (15) |
C22—C23—H23 | 120.9 | C16"—C15"—C14" | 118.61 (15) |
C23—C24—C25 | 122.98 (14) | C16"—C15"—H15" | 120.7 |
C23—C24—N2 | 118.73 (14) | C14"—C15"—H15" | 120.7 |
C25—C24—N2 | 118.29 (14) | C15"—C16"—C11" | 119.19 (16) |
C26—C25—C24 | 118.64 (15) | C15"—C16"—H16" | 120.4 |
C26—C25—H25 | 120.7 | C11"—C16"—H16" | 120.4 |
C24—C25—H25 | 120.7 | C22"—C21"—C26" | 121.88 (16) |
C25—C26—C21 | 118.43 (15) | C22"—C21"—O3" | 122.83 (14) |
C25—C26—H26 | 120.8 | C26"—C21"—O3" | 115.22 (15) |
C21—C26—H26 | 120.8 | C21"—C22"—C23" | 118.68 (15) |
C1'—O2'—C11' | 118.11 (12) | C21"—C22"—H22" | 120.7 |
C1'—O3'—C21' | 116.13 (12) | C23"—C22"—H22" | 120.7 |
O4'—N1'—O5' | 123.30 (14) | C24"—C23"—C22" | 118.99 (16) |
O4'—N1'—C14' | 118.20 (14) | C24"—C23"—H23" | 120.5 |
O5'—N1'—C14' | 118.49 (13) | C22"—C23"—H23" | 120.5 |
O6'—N2'—O7' | 123.29 (14) | C25"—C24"—C23" | 122.78 (16) |
O6'—N2'—C24' | 118.08 (13) | C25"—C24"—N2" | 118.87 (14) |
O7'—N2'—C24' | 118.63 (13) | C23"—C24"—N2" | 118.34 (15) |
O1'—C1'—O2' | 127.94 (15) | C24"—C25"—C26" | 118.17 (15) |
O1'—C1'—O3' | 126.85 (15) | C24"—C25"—H25" | 120.9 |
O2'—C1'—O3' | 105.20 (13) | C26"—C25"—H25" | 120.9 |
C16'—C11'—C12' | 122.75 (15) | C25"—C26"—C21" | 119.49 (16) |
C16'—C11'—O2' | 120.87 (14) | C25"—C26"—H26" | 120.3 |
C12'—C11'—O2' | 116.11 (13) | C21"—C26"—H26" | 120.3 |
C11'—C12'—C13' | 118.54 (15) | C106—C101—C102 | 121.0 (2) |
C11'—C12'—H12' | 120.7 | C106—C101—H101 | 119.5 |
C13'—C12'—H12' | 120.7 | C102—C101—H101 | 119.5 |
C14'—C13'—C12' | 118.52 (15) | C101—C102—C103 | 118.7 (2) |
C14'—C13'—H13' | 120.7 | C101—C102—H102 | 120.6 |
C12'—C13'—H13' | 120.7 | C103—C102—H102 | 120.6 |
C13'—C14'—C15' | 122.76 (15) | C104—C103—C102 | 118.7 (2) |
C13'—C14'—N1' | 118.68 (15) | C104—C103—H103 | 120.6 |
C15'—C14'—N1' | 118.57 (14) | C102—C103—H103 | 120.6 |
C16'—C15'—C14' | 118.66 (14) | C105—C104—C103 | 120.2 (2) |
C16'—C15'—H15' | 120.7 | C105—C104—H104 | 119.9 |
C14'—C15'—H15' | 120.7 | C103—C104—H104 | 119.9 |
C15'—C16'—C11' | 118.77 (15) | C106—C105—C104 | 120.8 (2) |
C15'—C16'—H16' | 120.6 | C106—C105—H105 | 119.6 |
C11'—C16'—H16' | 120.6 | C104—C105—H105 | 119.6 |
C22'—C21'—C26' | 123.06 (15) | C105—C106—C101 | 120.6 (2) |
C22'—C21'—O3' | 119.35 (13) | C105—C106—H106 | 119.7 |
C26'—C21'—O3' | 117.36 (14) | C101—C106—H106 | 119.7 |
C21'—C22'—C23' | 118.87 (14) | ||
C21—O3—C1—O1 | 0.1 (3) | C1'—O3'—C21'—C26' | −122.45 (15) |
C21—O3—C1—O2 | 179.47 (13) | C26'—C21'—C22'—C23' | 1.4 (3) |
C11—O2—C1—O1 | −1.4 (3) | O3'—C21'—C22'—C23' | 175.75 (14) |
C11—O2—C1—O3 | 179.22 (13) | C21'—C22'—C23'—C24' | −1.8 (2) |
C1—O2—C11—C16 | −50.0 (2) | C22'—C23'—C24'—C25' | 0.8 (3) |
C1—O2—C11—C12 | 136.11 (15) | C22'—C23'—C24'—N2' | −178.46 (15) |
C16—C11—C12—C13 | −1.5 (2) | O6'—N2'—C24'—C25' | −18.3 (2) |
O2—C11—C12—C13 | 172.42 (14) | O7'—N2'—C24'—C25' | 161.38 (15) |
C11—C12—C13—C14 | 1.1 (2) | O6'—N2'—C24'—C23' | 161.01 (15) |
C12—C13—C14—C15 | 0.1 (2) | O7'—N2'—C24'—C23' | −19.3 (2) |
C12—C13—C14—N1 | −177.39 (14) | C23'—C24'—C25'—C26' | 0.7 (3) |
O5—N1—C14—C13 | 10.4 (2) | N2'—C24'—C25'—C26' | −179.99 (14) |
O4—N1—C14—C13 | −170.71 (15) | C22'—C21'—C26'—C25' | 0.2 (3) |
O5—N1—C14—C15 | −167.23 (14) | O3'—C21'—C26'—C25' | −174.29 (14) |
O4—N1—C14—C15 | 11.7 (2) | C24'—C25'—C26'—C21' | −1.2 (2) |
C13—C14—C15—C16 | −1.1 (2) | C11"—O2"—C1"—O1" | −6.6 (2) |
N1—C14—C15—C16 | 176.41 (14) | C11"—O2"—C1"—O3" | 173.48 (12) |
C12—C11—C16—C15 | 0.5 (2) | C21"—O3"—C1"—O1" | 3.1 (2) |
O2—C11—C16—C15 | −172.94 (14) | C21"—O3"—C1"—O2" | −176.93 (13) |
C14—C15—C16—C11 | 0.8 (2) | C1"—O2"—C11"—C12" | −49.0 (2) |
C1—O3—C21—C22 | 64.8 (2) | C1"—O2"—C11"—C16" | 137.01 (15) |
C1—O3—C21—C26 | −120.47 (16) | C16"—C11"—C12"—C13" | 0.9 (2) |
C26—C21—C22—C23 | 0.5 (3) | O2"—C11"—C12"—C13" | −172.72 (14) |
O3—C21—C22—C23 | 174.87 (14) | C11"—C12"—C13"—C14" | 0.7 (2) |
C21—C22—C23—C24 | 0.1 (2) | C12"—C13"—C14"—C15" | −1.6 (2) |
C22—C23—C24—C25 | −0.6 (2) | C12"—C13"—C14"—N1" | 177.57 (14) |
C22—C23—C24—N2 | 179.38 (14) | O5"—N1"—C14"—C15" | −179.38 (17) |
O7—N2—C24—C23 | 4.3 (2) | O4"—N1"—C14"—C15" | 0.9 (2) |
O6—N2—C24—C23 | −176.37 (15) | O5"—N1"—C14"—C13" | 1.5 (2) |
O7—N2—C24—C25 | −175.77 (15) | O4"—N1"—C14"—C13" | −178.25 (15) |
O6—N2—C24—C25 | 3.6 (2) | C13"—C14"—C15"—C16" | 0.9 (2) |
C23—C24—C25—C26 | 0.4 (2) | N1"—C14"—C15"—C16" | −178.23 (14) |
N2—C24—C25—C26 | −179.53 (14) | C14"—C15"—C16"—C11" | 0.6 (2) |
C24—C25—C26—C21 | 0.2 (2) | C12"—C11"—C16"—C15" | −1.5 (2) |
C22—C21—C26—C25 | −0.7 (3) | O2"—C11"—C16"—C15" | 172.47 (14) |
O3—C21—C26—C25 | −175.28 (14) | C1"—O3"—C21"—C22" | −49.0 (2) |
C11'—O2'—C1'—O1' | −6.9 (2) | C1"—O3"—C21"—C26" | 134.02 (16) |
C11'—O2'—C1'—O3' | 174.26 (12) | C26"—C21"—C22"—C23" | −1.2 (3) |
C21'—O3'—C1'—O1' | 14.2 (2) | O3"—C21"—C22"—C23" | −177.98 (15) |
C21'—O3'—C1'—O2' | −166.98 (11) | C21"—C22"—C23"—C24" | 0.8 (3) |
C1'—O2'—C11'—C16' | −54.98 (19) | C22"—C23"—C24"—C25" | 0.1 (3) |
C1'—O2'—C11'—C12' | 130.82 (15) | C22"—C23"—C24"—N2" | 178.95 (15) |
C16'—C11'—C12'—C13' | 0.7 (2) | O6"—N2"—C24"—C25" | −177.28 (17) |
O2'—C11'—C12'—C13' | 174.75 (13) | O7"—N2"—C24"—C25" | 3.1 (2) |
C11'—C12'—C13'—C14' | 0.0 (2) | O6"—N2"—C24"—C23" | 3.8 (2) |
C12'—C13'—C14'—C15' | −0.2 (2) | O7"—N2"—C24"—C23" | −175.76 (16) |
C12'—C13'—C14'—N1' | −179.65 (13) | C23"—C24"—C25"—C26" | −0.7 (3) |
O4'—N1'—C14'—C13' | 171.67 (14) | N2"—C24"—C25"—C26" | −179.52 (15) |
O5'—N1'—C14'—C13' | −7.9 (2) | C24"—C25"—C26"—C21" | 0.3 (3) |
O4'—N1'—C14'—C15' | −7.8 (2) | C22"—C21"—C26"—C25" | 0.7 (3) |
O5'—N1'—C14'—C15' | 172.61 (14) | O3"—C21"—C26"—C25" | 177.64 (15) |
C13'—C14'—C15'—C16' | −0.2 (2) | C106—C101—C102—C103 | −0.3 (3) |
N1'—C14'—C15'—C16' | 179.23 (13) | C101—C102—C103—C104 | 0.1 (3) |
C14'—C15'—C16'—C11' | 0.8 (2) | C102—C103—C104—C105 | 0.1 (3) |
C12'—C11'—C16'—C15' | −1.1 (2) | C103—C104—C105—C106 | −0.2 (3) |
O2'—C11'—C16'—C15' | −174.90 (13) | C104—C105—C106—C101 | 0.1 (3) |
C1'—O3'—C21'—C22' | 62.84 (19) | C102—C101—C106—C105 | 0.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23···O2i | 0.95 | 2.60 | 3.249 (2) | 126 |
C16′—H16′···O4ii | 0.95 | 2.56 | 3.476 (2) | 161 |
C22′—H22′···O4ii | 0.95 | 2.55 | 3.495 (2) | 174 |
C22′—H22′···O5ii | 0.95 | 2.64 | 3.3478 (19) | 132 |
C15—H15···O6i | 0.95 | 2.59 | 3.356 (2) | 138 |
C13—H13···O7iii | 0.95 | 2.47 | 3.210 (2) | 134 |
C16"—H16"···O1′iv | 0.95 | 2.48 | 3.203 (2) | 133 |
C26′—H26′···O4′v | 0.95 | 2.62 | 3.2461 (19) | 124 |
C22"—H22"···O5′v | 0.95 | 2.67 | 3.418 (2) | 136 |
C23"—H23"···O5′vi | 0.95 | 2.54 | 3.256 (2) | 132 |
C12"—H12"···O6′ | 0.95 | 2.60 | 3.439 (2) | 147 |
C22—H22···O7′vii | 0.95 | 2.56 | 3.3540 (19) | 141 |
C25′—H25′···O1" | 0.95 | 2.58 | 3.4736 (19) | 157 |
C12′—H12′···O7"viii | 0.95 | 2.56 | 3.357 (2) | 142 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x, −y+1, −z; (iii) x, −y+1/2, z−1/2; (iv) x, −y+3/2, z+1/2; (v) x, −y+1/2, z+1/2; (vi) −x+1, y+1/2, −z+1/2; (vii) −x, y−1/2, −z+1/2; (viii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C13H8N2O7·1/3C6H6 |
Mr | 330.25 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 133 |
a, b, c (Å) | 21.074 (2), 8.4949 (8), 25.828 (2) |
β (°) | 111.618 (5) |
V (Å3) | 4298.6 (7) |
Z | 12 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.40 × 0.25 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26129, 8781, 5569 |
Rint | 0.048 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.079, 0.92 |
No. of reflections | 8781 |
No. of parameters | 649 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.21 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1994), SHELXL97.
O1—C1 | 1.1809 (19) | O3'—C1' | 1.3514 (19) |
O2—C1 | 1.3494 (19) | O3'—C21' | 1.4087 (18) |
O2—C11 | 1.3981 (18) | O1"—C1" | 1.1839 (19) |
O3—C1 | 1.3466 (19) | O2"—C1" | 1.3458 (19) |
O3—C21 | 1.4019 (18) | O2"—C11" | 1.4070 (19) |
O1'—C1' | 1.1872 (19) | O3"—C1" | 1.355 (2) |
O2'—C1' | 1.3448 (19) | O3"—C21" | 1.4024 (19) |
O2'—C11' | 1.4061 (18) | ||
O1—C1—O3 | 127.89 (15) | O2'—C1'—O3' | 105.20 (13) |
O1—C1—O2 | 128.36 (15) | O1"—C1"—O2" | 127.82 (16) |
O3—C1—O2 | 103.74 (14) | O1"—C1"—O3" | 127.52 (16) |
O1'—C1'—O2' | 127.94 (15) | O2"—C1"—O3" | 104.66 (14) |
O1'—C1'—O3' | 126.85 (15) | ||
C21—O3—C1—O1 | 0.1 (3) | C21'—O3'—C1'—O1' | 14.2 (2) |
C11—O2—C1—O1 | −1.4 (3) | C11"—O2"—C1"—O1" | −6.6 (2) |
C11'—O2'—C1'—O1' | −6.9 (2) | C21"—O3"—C1"—O1" | 3.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23···O2i | 0.95 | 2.60 | 3.249 (2) | 126.3 |
C16'—H16'···O4ii | 0.95 | 2.56 | 3.476 (2) | 161.2 |
C22'—H22'···O4ii | 0.95 | 2.55 | 3.495 (2) | 174.1 |
C22'—H22'···O5ii | 0.95 | 2.64 | 3.3478 (19) | 131.9 |
C15—H15···O6i | 0.95 | 2.59 | 3.356 (2) | 138.2 |
C13—H13···O7iii | 0.95 | 2.47 | 3.210 (2) | 134.2 |
C16"—H16"···O1'iv | 0.95 | 2.48 | 3.203 (2) | 133.1 |
C26'—H26'···O4'v | 0.95 | 2.62 | 3.2461 (19) | 124.1 |
C22"—H22"···O5'v | 0.95 | 2.67 | 3.418 (2) | 135.6 |
C23"—H23"···O5'vi | 0.95 | 2.54 | 3.256 (2) | 132.1 |
C12"—H12"···O6' | 0.95 | 2.60 | 3.439 (2) | 146.8 |
C22—H22···O7'vii | 0.95 | 2.56 | 3.3540 (19) | 140.9 |
C25'—H25'···O1" | 0.95 | 2.58 | 3.4736 (19) | 156.5 |
C12'—H12'···O7"viii | 0.95 | 2.56 | 3.357 (2) | 142.0 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x, −y+1, −z; (iii) x, −y+1/2, z−1/2; (iv) x, −y+3/2, z+1/2; (v) x, −y+1/2, z+1/2; (vi) −x+1, y+1/2, −z+1/2; (vii) −x, y−1/2, −z+1/2; (viii) x, y−1, z. |
In the previous paper (Simon et al., 2003) we presented introductory material concerning diaryl carbonates, together with the structure of bis(o-nitrophenyl) carbonate. Here we present the structure of the isomeric bis(p-nitrophenyl) carbonate (I), which crystallizes from benzene as a solvate in which the asymmetric unit contains three molecules of (I) and one of benzene (Fig. 1). Atoms of the second and third independent molecules are distinguished by primes and double primes respectively.
The carbonate moieties all display the s-cis–s-cis conformation (cf. torsion angles in Table 1); the largest deviation of an ipso carbon from the carbonate plane (defined by the four atoms C1, O1; O2, O3) is 0.289 (2) Å for C21'. The aromatic rings are inclined to the carbonate plane at angles varying from 45 to 68° (for details see supplementary material).
Bond lengths and angles of the carbonate moieties (Table 1) may be considered normal, although the angle O2—C1—O3 is among the narrowest recorded for a diaryl carbonate.
There are eight short intramolecular contacts X···O (X = C,N,O) (see Supp. Mat.). The molecular packing also involves a series of C—H···O hydrogen bonds (Table 2). However, perhaps the most striking feature of the packing is the C104—H104···π contact involving the benzene ring and the centroid of C11'–C16', with normalized H···π 2.73 Å, angle 172°. This can be recognized in Fig. 1.