Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013705/ya2006sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013705/ya2006Isup2.hkl |
CCDC reference: 608539
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.008 Å
- R factor = 0.076
- wR factor = 0.214
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N
Alert level C ABSMU01_ALERT_1_C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.094 Value of mu given = 0.090 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 42 Perc. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.87 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N' PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT480_ALERT_4_C Long H...A H-Bond Reported H2' .. O2 .. 2.67 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. O2' .. 2.69 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C31 H22 N2 O6
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4-PC Software (Enraf–Nonius, 1993); cell refinement: CAD-4-PC Software; data reduction: DATRD2 in NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).
C31H22N2O6 | F(000) = 1080 |
Mr = 518.51 | Dx = 1.343 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 13.438 (2) Å | θ = 20.0–25.0° |
b = 14.490 (3) Å | µ = 0.09 mm−1 |
c = 13.974 (3) Å | T = 295 K |
β = 109.505 (5)° | Plate, yellow |
V = 2564.8 (9) Å3 | 0.32 × 0.29 × 0.13 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | θmax = 25.1°, θmin = 1.8° |
Radiation source: fine-focus sealed tube | h = −16→15 |
Graphite monochromator | k = 0→17 |
ω scans | l = 0→16 |
4554 measured reflections | 3 standard reflections every 120 min |
4554 independent reflections | intensity decay: 1.1% |
1912 reflections with I > 2σ(I) |
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)] = 0.076 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.214 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0908P)2] where P = (Fo2 + 2Fc2)/3 |
4554 reflections | (Δ/σ)max < 0.001 |
352 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
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) - 5.8565 (0.0154) x + 10.3861 (0.0066) y + 9.2033 (0.0075) z = 17.9254 (0.0211) * -0.0234 (0.0052) C1 * -0.0282 (0.0055) C2 * -0.0125 (0.0048) C3 * 0.0026 (0.0042) C4 * 0.0010 (0.0041) C4A * 0.0619 (0.0051) C9 * 0.0188 (0.0045) C9A * 0.0040 (0.0044) C5 * -0.0197 (0.0055) C6 * -0.0305 (0.0061) C7 * -0.0112 (0.0052) C8 * 0.0123 (0.0047) C8A * 0.0166 (0.0038) C10 * 0.0082 (0.0041) C10A Rms deviation of fitted atoms = 0.0234 - 0.9842 (0.0157) x + 10.4475 (0.0062) y + 9.4178 (0.0062) z = 16.7212 (0.0108) Angle to previous plane (with approximate e.s.d.) = 22.51 (0.09) * -0.0210 (0.0045) C1' * -0.0326 (0.0051) C2' * -0.0045 (0.0051) C3' * 0.0151 (0.0044) C4' * 0.0173 (0.0040) C4A' * 0.0286 (0.0044) C9' * -0.0024 (0.0043) C9A' * -0.0179 (0.0040) C5' * -0.0349 (0.0045) C6' * -0.0037 (0.0051) C7' * 0.0157 (0.0047) C8' * 0.0198 (0.0043) C8A' * 0.0273 (0.0036) C10' * -0.0066 (0.0039) C10A' Rms deviation of fitted atoms = 0.0204 |
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 | 0.6501 (3) | 0.8155 (3) | 1.6982 (3) | 0.0824 (12) | |
O2 | 0.5262 (3) | 0.7478 (4) | 1.5921 (4) | 0.142 (2) | |
O9 | 1.0146 (3) | 0.7358 (4) | 1.7797 (3) | 0.1274 (19) | |
O1' | 0.6649 (3) | 0.3216 (2) | 1.2418 (3) | 0.0724 (11) | |
O2' | 0.5424 (3) | 0.4161 (3) | 1.2316 (3) | 0.0997 (16) | |
O9' | 1.0343 (2) | 0.4184 (3) | 1.4236 (3) | 0.0900 (13) | |
N | 0.6169 (3) | 0.7578 (3) | 1.6353 (3) | 0.0570 (11) | |
N' | 0.6317 (3) | 0.3880 (3) | 1.2705 (3) | 0.0494 (10) | |
C1 | 0.9345 (5) | 0.8340 (4) | 1.5986 (5) | 0.0827 (19) | |
H1 | 1.0061 | 0.8399 | 1.6348 | 0.099* | |
C2 | 0.8909 (7) | 0.8850 (5) | 1.5129 (6) | 0.096 (2) | |
H2 | 0.9319 | 0.9261 | 1.491 | 0.115* | |
C3 | 0.7871 (6) | 0.8747 (4) | 1.4601 (5) | 0.0799 (18) | |
H3 | 0.7568 | 0.9095 | 1.4017 | 0.096* | |
C4 | 0.7256 (4) | 0.8143 (3) | 1.4907 (4) | 0.0574 (14) | |
H4 | 0.6543 | 0.8086 | 1.453 | 0.069* | |
C4A | 0.7685 (3) | 0.7619 (3) | 1.5770 (3) | 0.0411 (11) | |
C5 | 0.6958 (4) | 0.5779 (4) | 1.7388 (4) | 0.0656 (15) | |
H5 | 0.6242 | 0.5698 | 1.7038 | 0.079* | |
C6 | 0.7437 (7) | 0.5267 (4) | 1.8245 (5) | 0.092 (2) | |
H6 | 0.7043 | 0.4841 | 1.8464 | 0.11* | |
C7 | 0.8480 (8) | 0.5374 (5) | 1.8775 (5) | 0.103 (2) | |
H7 | 0.8798 | 0.5022 | 1.9353 | 0.124* | |
C8 | 0.9049 (5) | 0.5995 (5) | 1.8458 (4) | 0.0848 (19) | |
H8 | 0.9763 | 0.6071 | 1.8824 | 0.102* | |
C8A | 0.8586 (4) | 0.6524 (4) | 1.7592 (4) | 0.0556 (13) | |
C9 | 0.9224 (4) | 0.7210 (4) | 1.7277 (4) | 0.0718 (17) | |
C9A | 0.8730 (3) | 0.7727 (3) | 1.6333 (3) | 0.0518 (13) | |
C10 | 0.6986 (3) | 0.6962 (3) | 1.6083 (3) | 0.0381 (11) | |
C10A | 0.7531 (3) | 0.6415 (3) | 1.7039 (3) | 0.0435 (11) | |
C11 | 0.6376 (3) | 0.6339 (3) | 1.5206 (3) | 0.0441 (12) | |
H11A | 0.5894 | 0.5958 | 1.5419 | 0.053* | |
H11B | 0.5957 | 0.6719 | 1.4644 | 0.053* | |
C12 | 0.7094 (3) | 0.5715 (3) | 1.4842 (3) | 0.0418 (11) | |
H12A | 0.7567 | 0.6091 | 1.461 | 0.05* | |
H12B | 0.7519 | 0.5334 | 1.5399 | 0.05* | |
C1' | 0.9300 (4) | 0.5421 (4) | 1.2691 (4) | 0.0679 (16) | |
H1' | 1.0024 | 0.5352 | 1.2839 | 0.082* | |
C2' | 0.8775 (6) | 0.6013 (4) | 1.1967 (5) | 0.0849 (19) | |
H2' | 0.913 | 0.6343 | 1.1609 | 0.102* | |
C3' | 0.7724 (6) | 0.6132 (4) | 1.1755 (5) | 0.0814 (18) | |
H3' | 0.7363 | 0.6552 | 1.1257 | 0.098* | |
C4' | 0.7186 (4) | 0.5642 (3) | 1.2263 (4) | 0.0600 (14) | |
H4' | 0.6463 | 0.5729 | 1.2104 | 0.072* | |
C4A' | 0.7704 (3) | 0.5023 (3) | 1.3006 (3) | 0.0394 (11) | |
C5' | 0.7235 (4) | 0.3268 (3) | 1.4867 (4) | 0.0540 (13) | |
H5' | 0.6512 | 0.3324 | 1.4734 | 0.065* | |
C6' | 0.7817 (6) | 0.2653 (4) | 1.5591 (4) | 0.0745 (17) | |
H6' | 0.7474 | 0.2285 | 1.5929 | 0.089* | |
C7' | 0.8884 (6) | 0.2574 (4) | 1.5824 (4) | 0.086 (2) | |
H7' | 0.9267 | 0.2166 | 1.6326 | 0.103* | |
C8' | 0.9381 (5) | 0.3100 (4) | 1.5314 (4) | 0.0706 (16) | |
H8' | 1.0107 | 0.3042 | 1.5464 | 0.085* | |
C8A' | 0.8822 (3) | 0.3719 (3) | 1.4572 (3) | 0.0469 (12) | |
C9' | 0.9391 (4) | 0.4265 (4) | 1.4035 (4) | 0.0564 (14) | |
C9A' | 0.8788 (3) | 0.4903 (3) | 1.3231 (4) | 0.0465 (12) | |
C10' | 0.7091 (3) | 0.4481 (3) | 1.3555 (3) | 0.0361 (10) | |
C10A' | 0.7731 (3) | 0.3801 (3) | 1.4339 (3) | 0.0390 (11) | |
C11' | 0.6434 (3) | 0.5108 (3) | 1.3983 (3) | 0.0421 (11) | |
H11C | 0.5993 | 0.5496 | 1.3443 | 0.051* | |
H11D | 0.5973 | 0.473 | 1.4227 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.079 (3) | 0.080 (3) | 0.096 (3) | 0.003 (2) | 0.039 (2) | −0.036 (3) |
O2 | 0.043 (2) | 0.185 (5) | 0.190 (5) | 0.008 (3) | 0.030 (3) | −0.109 (4) |
O9 | 0.057 (3) | 0.201 (5) | 0.094 (3) | −0.048 (3) | −0.014 (2) | 0.012 (3) |
O1' | 0.084 (3) | 0.057 (2) | 0.071 (3) | −0.004 (2) | 0.019 (2) | −0.028 (2) |
O2' | 0.044 (2) | 0.119 (4) | 0.114 (3) | 0.002 (2) | −0.002 (2) | −0.056 (3) |
O9' | 0.0311 (19) | 0.118 (3) | 0.121 (3) | 0.010 (2) | 0.025 (2) | −0.002 (3) |
N | 0.044 (3) | 0.067 (3) | 0.063 (3) | 0.004 (2) | 0.023 (2) | −0.015 (2) |
N' | 0.049 (3) | 0.047 (3) | 0.052 (3) | −0.005 (2) | 0.015 (2) | −0.012 (2) |
C1 | 0.069 (4) | 0.096 (5) | 0.086 (5) | −0.042 (4) | 0.030 (4) | −0.024 (4) |
C2 | 0.119 (6) | 0.085 (5) | 0.111 (6) | −0.041 (5) | 0.074 (5) | −0.010 (5) |
C3 | 0.117 (5) | 0.068 (4) | 0.071 (4) | 0.005 (4) | 0.054 (4) | 0.010 (3) |
C4 | 0.063 (3) | 0.060 (3) | 0.053 (3) | −0.001 (3) | 0.024 (3) | 0.003 (3) |
C4A | 0.040 (2) | 0.049 (3) | 0.036 (3) | −0.001 (2) | 0.016 (2) | −0.006 (2) |
C5 | 0.071 (3) | 0.068 (4) | 0.063 (4) | −0.010 (3) | 0.029 (3) | 0.001 (3) |
C6 | 0.134 (6) | 0.065 (4) | 0.088 (5) | −0.011 (4) | 0.054 (5) | 0.011 (4) |
C7 | 0.153 (8) | 0.080 (5) | 0.071 (5) | 0.017 (5) | 0.029 (5) | 0.032 (4) |
C8 | 0.083 (4) | 0.096 (5) | 0.060 (4) | 0.024 (4) | 0.003 (3) | 0.016 (4) |
C8A | 0.046 (3) | 0.065 (3) | 0.048 (3) | 0.005 (3) | 0.006 (2) | −0.001 (3) |
C9 | 0.039 (3) | 0.103 (5) | 0.063 (4) | −0.016 (3) | 0.003 (3) | −0.009 (3) |
C9A | 0.043 (3) | 0.063 (3) | 0.051 (3) | −0.019 (3) | 0.018 (2) | −0.011 (3) |
C10 | 0.028 (2) | 0.045 (3) | 0.043 (3) | 0.002 (2) | 0.015 (2) | −0.008 (2) |
C10A | 0.042 (3) | 0.047 (3) | 0.045 (3) | 0.002 (2) | 0.019 (2) | −0.006 (2) |
C11 | 0.028 (2) | 0.054 (3) | 0.053 (3) | −0.001 (2) | 0.015 (2) | −0.010 (2) |
C12 | 0.031 (2) | 0.051 (3) | 0.046 (3) | −0.005 (2) | 0.016 (2) | −0.014 (2) |
C1' | 0.063 (4) | 0.074 (4) | 0.082 (4) | −0.015 (3) | 0.044 (3) | −0.009 (3) |
C2' | 0.109 (5) | 0.072 (4) | 0.099 (5) | −0.026 (4) | 0.068 (5) | 0.004 (4) |
C3' | 0.111 (5) | 0.059 (4) | 0.081 (4) | 0.006 (4) | 0.042 (4) | 0.026 (3) |
C4' | 0.059 (3) | 0.053 (3) | 0.073 (4) | 0.005 (3) | 0.028 (3) | 0.019 (3) |
C4A' | 0.037 (2) | 0.036 (3) | 0.045 (3) | −0.001 (2) | 0.014 (2) | −0.002 (2) |
C5' | 0.061 (3) | 0.054 (3) | 0.053 (3) | 0.000 (3) | 0.028 (3) | 0.006 (3) |
C6' | 0.114 (5) | 0.055 (4) | 0.059 (4) | 0.008 (4) | 0.035 (4) | 0.012 (3) |
C7' | 0.111 (5) | 0.076 (5) | 0.056 (4) | 0.037 (4) | 0.010 (4) | 0.017 (3) |
C8' | 0.066 (4) | 0.072 (4) | 0.065 (4) | 0.025 (3) | 0.009 (3) | 0.005 (3) |
C8A' | 0.039 (3) | 0.050 (3) | 0.047 (3) | 0.010 (2) | 0.008 (2) | −0.001 (2) |
C9' | 0.034 (3) | 0.066 (4) | 0.069 (3) | 0.003 (3) | 0.018 (3) | −0.013 (3) |
C9A' | 0.041 (3) | 0.046 (3) | 0.059 (3) | −0.006 (2) | 0.026 (2) | −0.006 (3) |
C10' | 0.030 (2) | 0.039 (3) | 0.038 (2) | −0.007 (2) | 0.0104 (19) | −0.011 (2) |
C10A' | 0.041 (2) | 0.037 (3) | 0.040 (3) | 0.003 (2) | 0.013 (2) | −0.003 (2) |
C11' | 0.032 (2) | 0.049 (3) | 0.046 (3) | −0.004 (2) | 0.015 (2) | −0.004 (2) |
O1—N | 1.187 (5) | C11—C12 | 1.528 (5) |
O2—N | 1.175 (5) | C11—H11A | 0.97 |
O9—C9 | 1.228 (5) | C11—H11B | 0.97 |
O1'—N' | 1.185 (4) | C12—C11' | 1.514 (5) |
O2'—N' | 1.210 (5) | C12—H12A | 0.97 |
O9'—C9' | 1.221 (5) | C12—H12B | 0.97 |
N—C10 | 1.554 (5) | C1'—C2' | 1.334 (8) |
N'—C10' | 1.558 (5) | C1'—C9A' | 1.398 (6) |
C1—C2 | 1.362 (8) | C1'—H1' | 0.93 |
C1—C9A | 1.405 (7) | C2'—C3' | 1.354 (8) |
C1—H1 | 0.93 | C2'—H2' | 0.93 |
C2—C3 | 1.351 (8) | C3'—C4' | 1.370 (7) |
C2—H2 | 0.93 | C3'—H3' | 0.93 |
C3—C4 | 1.366 (7) | C4'—C4A' | 1.372 (6) |
C3—H3 | 0.93 | C4'—H4' | 0.93 |
C4—C4A | 1.379 (6) | C4A'—C9A' | 1.396 (5) |
C4—H4 | 0.93 | C4A'—C10' | 1.519 (5) |
C4A—C9A | 1.371 (6) | C5'—C6' | 1.378 (7) |
C4A—C10 | 1.501 (6) | C5'—C10A' | 1.384 (6) |
C5—C6 | 1.371 (8) | C5'—H5' | 0.93 |
C5—C10A | 1.390 (6) | C6'—C7' | 1.366 (8) |
C5—H5 | 0.93 | C6'—H6' | 0.93 |
C6—C7 | 1.357 (9) | C7'—C8' | 1.361 (8) |
C6—H6 | 0.93 | C7'—H7' | 0.93 |
C7—C8 | 1.348 (8) | C8'—C8A' | 1.387 (6) |
C7—H7 | 0.93 | C8'—H8' | 0.93 |
C8—C8A | 1.391 (7) | C8A'—C10A' | 1.396 (6) |
C8—H8 | 0.93 | C8A'—C9' | 1.469 (7) |
C8A—C10A | 1.380 (6) | C9'—C9A' | 1.472 (6) |
C8A—C9 | 1.473 (7) | C10'—C11' | 1.522 (5) |
C9—C9A | 1.469 (7) | C10'—C10A' | 1.510 (6) |
C10—C10A | 1.515 (6) | C11'—H11C | 0.97 |
C10—C11 | 1.523 (5) | C11'—H11D | 0.97 |
O1—N—O2 | 122.4 (4) | C11'—C12—C11 | 109.8 (3) |
O1—N—C10 | 117.6 (4) | C11'—C12—H12A | 109.7 |
O2—N—C10 | 120.0 (4) | C11—C12—H12A | 109.7 |
O1'—N'—O2' | 123.4 (4) | C11'—C12—H12B | 109.7 |
O1'—N'—C10' | 118.7 (4) | C11—C12—H12B | 109.7 |
O2'—N'—C10' | 117.6 (4) | H12A—C12—H12B | 108.2 |
C2—C1—C9A | 121.1 (6) | C2'—C1'—C9A' | 121.6 (5) |
C2—C1—H1 | 119.4 | C2'—C1'—H1' | 119.2 |
C9A—C1—H1 | 119.4 | C9A'—C1'—H1' | 119.2 |
C1—C2—C3 | 118.8 (6) | C1'—C2'—C3' | 119.8 (6) |
C1—C2—H2 | 120.6 | C1'—C2'—H2' | 120.1 |
C3—C2—H2 | 120.6 | C3'—C2'—H2' | 120.1 |
C2—C3—C4 | 121.5 (6) | C2'—C3'—C4' | 120.9 (6) |
C2—C3—H3 | 119.2 | C2'—C3'—H3' | 119.6 |
C4—C3—H3 | 119.2 | C4'—C3'—H3' | 119.6 |
C3—C4—C4A | 120.4 (5) | C4A'—C4'—C3' | 120.6 (5) |
C3—C4—H4 | 119.8 | C4A'—C4'—H4' | 119.7 |
C4A—C4—H4 | 119.8 | C3'—C4'—H4' | 119.7 |
C9A—C4A—C4 | 119.2 (5) | C4'—C4A'—C9A' | 118.7 (4) |
C9A—C4A—C10 | 121.8 (4) | C4'—C4A'—C10' | 119.8 (4) |
C4—C4A—C10 | 119.0 (4) | C9A'—C4A'—C10' | 121.5 (4) |
C6—C5—C10A | 120.8 (6) | C6'—C5'—C10A' | 119.7 (5) |
C6—C5—H5 | 119.6 | C6'—C5'—H5' | 120.1 |
C10A—C5—H5 | 119.6 | C10A'—C5'—H5' | 120.1 |
C7—C6—C5 | 120.9 (6) | C7'—C6'—C5' | 121.5 (6) |
C7—C6—H6 | 119.6 | C7'—C6'—H6' | 119.3 |
C5—C6—H6 | 119.6 | C5'—C6'—H6' | 119.3 |
C6—C7—C8 | 119.5 (6) | C6'—C7'—C8' | 119.2 (6) |
C6—C7—H7 | 120.3 | C6'—C7'—H7' | 120.4 |
C8—C7—H7 | 120.3 | C8'—C7'—H7' | 120.4 |
C7—C8—C8A | 121.0 (6) | C7'—C8'—C8A' | 121.0 (5) |
C7—C8—H8 | 119.5 | C7'—C8'—H8' | 119.5 |
C8A—C8—H8 | 119.5 | C8A'—C8'—H8' | 119.5 |
C10A—C8A—C8 | 120.1 (5) | C10A'—C8A'—C8' | 119.6 (5) |
C10A—C8A—C9 | 120.1 (5) | C10A'—C8A'—C9' | 121.3 (4) |
C8—C8A—C9 | 119.8 (5) | C8'—C8A'—C9' | 119.1 (5) |
O9—C9—C9A | 120.5 (5) | O9'—C9'—C9A' | 120.2 (5) |
O9—C9—C8A | 120.9 (5) | O9'—C9'—C8A' | 121.0 (5) |
C9A—C9—C8A | 118.7 (4) | C9A'—C9'—C8A' | 118.8 (4) |
C4A—C9A—C1 | 118.8 (5) | C4A'—C9A'—C1' | 118.4 (5) |
C4A—C9A—C9 | 121.8 (4) | C4A'—C9A'—C9' | 121.2 (4) |
C1—C9A—C9 | 119.4 (5) | C1'—C9A'—C9' | 120.4 (5) |
C4A—C10—C10A | 115.1 (3) | C11'—C10'—C10A' | 111.6 (4) |
C4A—C10—C11 | 111.2 (4) | C11'—C10'—C4A' | 111.9 (3) |
C10A—C10—C11 | 111.7 (4) | C10A'—C10'—C4A' | 115.5 (3) |
C4A—C10—N | 105.5 (3) | C11'—C10'—N' | 107.9 (3) |
C10A—C10—N | 105.0 (3) | C10A'—C10'—N' | 105.2 (3) |
C11—C10—N | 107.6 (3) | C4A'—C10'—N' | 104.0 (3) |
C5—C10A—C8A | 117.7 (5) | C5'—C10A'—C8A' | 118.9 (4) |
C5—C10A—C10 | 119.7 (4) | C5'—C10A'—C10' | 119.4 (4) |
C8A—C10A—C10 | 122.6 (4) | C8A'—C10A'—C10' | 121.6 (4) |
C12—C11—C10 | 112.9 (3) | C12—C11'—C10' | 113.3 (3) |
C12—C11—H11A | 109 | C12—C11'—H11C | 108.9 |
C10—C11—H11A | 109 | C10'—C11'—H11C | 108.9 |
C12—C11—H11B | 109 | C12—C11'—H11D | 108.9 |
C10—C11—H11B | 109 | C10'—C11'—H11D | 108.9 |
H11A—C11—H11B | 107.8 | H11C—C11'—H11D | 107.7 |
C9A—C1—C2—C3 | −1.0 (10) | C9A'—C1'—C2'—C3' | 1.1 (9) |
C1—C2—C3—C4 | −0.3 (10) | C1'—C2'—C3'—C4' | −1.0 (10) |
C2—C3—C4—C4A | −0.1 (9) | C2'—C3'—C4'—C4A' | 0.5 (9) |
C3—C4—C4A—C9A | 1.7 (7) | C3'—C4'—C4A'—C9A' | −0.1 (7) |
C3—C4—C4A—C10 | −179.9 (4) | C3'—C4'—C4A'—C10' | −179.5 (5) |
C10A—C5—C6—C7 | 0.4 (9) | C10A'—C5'—C6'—C7' | 1.8 (8) |
C5—C6—C7—C8 | 0.3 (11) | C5'—C6'—C7'—C8' | −1.4 (9) |
C6—C7—C8—C8A | −0.4 (11) | C6'—C7'—C8'—C8A' | 0.7 (9) |
C7—C8—C8A—C10A | −0.4 (9) | C7'—C8'—C8A'—C10A' | −0.5 (8) |
C7—C8—C8A—C9 | 178.7 (6) | C7'—C8'—C8A'—C9' | −179.4 (5) |
C10A—C8A—C9—O9 | 175.2 (5) | C10A'—C8A'—C9'—O9' | −179.3 (5) |
C8—C8A—C9—O9 | −3.8 (9) | C8'—C8A'—C9'—O9' | −0.4 (7) |
C10A—C8A—C9—C9A | −3.9 (8) | C10A'—C8A'—C9'—C9A' | −0.5 (7) |
C8—C8A—C9—C9A | 177.0 (5) | C8'—C8A'—C9'—C9A' | 178.4 (4) |
C4—C4A—C9A—C1 | −2.9 (7) | C4'—C4A'—C9A'—C1' | 0.1 (7) |
C10—C4A—C9A—C1 | 178.8 (4) | C10'—C4A'—C9A'—C1' | 179.5 (4) |
C4—C4A—C9A—C9 | 178.0 (5) | C4'—C4A'—C9A'—C9' | 178.6 (4) |
C10—C4A—C9A—C9 | −0.4 (7) | C10'—C4A'—C9A'—C9' | −2.0 (6) |
C2—C1—C9A—C4A | 2.6 (9) | C2'—C1'—C9A'—C4A' | −0.6 (8) |
C2—C1—C9A—C9 | −178.2 (6) | C2'—C1'—C9A'—C9' | −179.2 (5) |
O9—C9—C9A—C4A | −175.9 (5) | O9'—C9'—C9A'—C4A' | −178.5 (5) |
C8A—C9—C9A—C4A | 3.3 (8) | C8A'—C9'—C9A'—C4A' | 2.7 (7) |
O9—C9—C9A—C1 | 5.0 (9) | O9'—C9'—C9A'—C1' | 0.0 (7) |
C8A—C9—C9A—C1 | −175.9 (5) | C8A'—C9'—C9A'—C1' | −178.8 (4) |
C9A—C4A—C10—C10A | −1.9 (6) | C4'—C4A'—C10'—C11' | −52.4 (5) |
C4—C4A—C10—C10A | 179.8 (4) | C9A'—C4A'—C10'—C11' | 128.2 (4) |
C9A—C4A—C10—C11 | −130.2 (4) | C4'—C4A'—C10'—C10A' | 178.5 (4) |
C4—C4A—C10—C11 | 51.4 (5) | C9A'—C4A'—C10'—C10A' | −0.9 (6) |
C9A—C4A—C10—N | 113.4 (4) | C4'—C4A'—C10'—N' | 63.8 (5) |
C4—C4A—C10—N | −64.9 (5) | C9A'—C4A'—C10'—N' | −115.6 (4) |
O1—N—C10—C4A | −56.6 (5) | O1'—N'—C10'—C11' | −164.3 (4) |
O2—N—C10—C4A | 121.6 (5) | O2'—N'—C10'—C11' | 21.6 (5) |
O1—N—C10—C10A | 65.4 (5) | O1'—N'—C10'—C10A' | −45.1 (5) |
O2—N—C10—C10A | −116.4 (6) | O2'—N'—C10'—C10A' | 140.8 (4) |
O1—N—C10—C11 | −175.4 (4) | O1'—N'—C10'—C4A' | 76.7 (5) |
O2—N—C10—C11 | 2.8 (7) | O2'—N'—C10'—C4A' | −97.4 (5) |
C6—C5—C10A—C8A | −1.1 (7) | C6'—C5'—C10A'—C8A' | −1.5 (7) |
C6—C5—C10A—C10 | 179.2 (5) | C6'—C5'—C10A'—C10' | −179.3 (4) |
C8—C8A—C10A—C5 | 1.1 (7) | C8'—C8A'—C10A'—C5' | 0.9 (7) |
C9—C8A—C10A—C5 | −178.0 (5) | C9'—C8A'—C10A'—C5' | 179.8 (4) |
C8—C8A—C10A—C10 | −179.3 (4) | C8'—C8A'—C10A'—C10' | 178.6 (4) |
C9—C8A—C10A—C10 | 1.6 (7) | C9'—C8A'—C10A'—C10' | −2.4 (6) |
C4A—C10—C10A—C5 | −179.2 (4) | C11'—C10'—C10A'—C5' | 51.6 (5) |
C11—C10—C10A—C5 | −51.1 (5) | C4A'—C10'—C10A'—C5' | −179.2 (4) |
N—C10—C10A—C5 | 65.2 (5) | N'—C10'—C10A'—C5' | −65.2 (5) |
C4A—C10—C10A—C8A | 1.2 (6) | C11'—C10'—C10A'—C8A' | −126.2 (4) |
C11—C10—C10A—C8A | 129.3 (4) | C4A'—C10'—C10A'—C8A' | 3.1 (6) |
N—C10—C10A—C8A | −114.4 (5) | N'—C10'—C10A'—C8A' | 117.1 (4) |
C4A—C10—C11—C12 | 63.0 (5) | C11—C12—C11'—C10' | 178.4 (4) |
C10A—C10—C11—C12 | −67.1 (5) | C10A'—C10'—C11'—C12 | 63.3 (5) |
N—C10—C11—C12 | 178.1 (4) | C4A'—C10'—C11'—C12 | −67.8 (5) |
C10—C11—C12—C11' | 179.1 (4) | N'—C10'—C11'—C12 | 178.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2′—H2′···O2i | 0.93 | 2.67 | 3.586 (10) | 168 |
C4—H4···O9ii | 0.93 | 2.60 | 3.417 (6) | 147 |
C5—H5···O2′iii | 0.93 | 2.69 | 3.363 (7) | 130 |
C5′—H5′···O2iii | 0.93 | 2.53 | 3.343 (7) | 146 |
C7′—H7′···O2′iv | 0.93 | 2.57 | 3.473 (7) | 165 |
Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z+3; (iv) x+1/2, −y+1/2, z+1/2. |
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