Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805005106/fl6149sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805005106/fl61492sup2.hkl |
CCDC reference: 269561
Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C12H17N3O7 | F(000) = 664 |
Mr = 315.29 | Dx = 1.333 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P2yb | Cell parameters from 6342 reflections |
a = 10.8447 (6) Å | θ = 2.7–30.6° |
b = 8.3527 (5) Å | µ = 0.11 mm−1 |
c = 17.443 (1) Å | T = 200 K |
β = 96.257 (1)° | Block, colourless |
V = 1570.62 (16) Å3 | 0.46 × 0.42 × 0.40 mm |
Z = 4 |
Bruker SMART APEX CCD diffractometer | 4157 independent reflections |
Radiation source: fine-focus sealed tube | 3917 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
φ and ω scans | θmax = 28.3°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003) | h = −14→14 |
Tmin = 0.868, Tmax = 0.96 | k = −11→11 |
16017 measured reflections | l = −23→23 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0699P)2 + 0.1865P] where P = (Fo2 + 2Fc2)/3 |
4157 reflections | (Δ/σ)max < 0.001 |
405 parameters | Δρmax = 0.34 e Å−3 |
1 restraint | Δρmin = −0.27 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. |
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 | 0.93305 (17) | 0.4305 (3) | 0.57496 (11) | 0.0407 (4) | |
H1 | 1.0110 | 0.3707 | 0.5682 | 0.049* | |
C2 | 0.82932 (17) | 0.3102 (3) | 0.58071 (11) | 0.0374 (4) | |
H2 | 0.8541 | 0.2327 | 0.6233 | 0.045* | |
C3 | 0.80075 (16) | 0.2201 (2) | 0.50531 (11) | 0.0356 (4) | |
H3 | 0.8725 | 0.1491 | 0.4974 | 0.043* | |
C4 | 0.77867 (16) | 0.3345 (2) | 0.43771 (10) | 0.0361 (4) | |
H4 | 0.6999 | 0.3957 | 0.4398 | 0.043* | |
C5 | 0.88961 (17) | 0.4477 (3) | 0.43886 (11) | 0.0380 (4) | |
H5 | 0.9661 | 0.3826 | 0.4351 | 0.046* | |
C6 | 0.9563 (2) | 0.5361 (4) | 0.64552 (13) | 0.0545 (6) | |
H6A | 0.8859 | 0.6088 | 0.6479 | 0.082* | |
H6B | 1.0320 | 0.5987 | 0.6425 | 0.082* | |
H6C | 0.9661 | 0.4692 | 0.6919 | 0.082* | |
C7 | 0.6714 (2) | 0.3614 (3) | 0.66307 (13) | 0.0481 (5) | |
C8 | 0.5643 (2) | 0.4664 (4) | 0.67487 (14) | 0.0564 (6) | |
H8A | 0.5708 | 0.5015 | 0.7288 | 0.085* | |
H8B | 0.4869 | 0.4067 | 0.6626 | 0.085* | |
H8C | 0.5646 | 0.5600 | 0.6411 | 0.085* | |
C9 | 0.7082 (2) | −0.0255 (3) | 0.53588 (12) | 0.0457 (5) | |
C10 | 0.5883 (3) | −0.1121 (4) | 0.53651 (15) | 0.0668 (8) | |
H10A | 0.5496 | −0.0819 | 0.5826 | 0.100* | |
H10B | 0.6035 | −0.2278 | 0.5370 | 0.100* | |
H10C | 0.5330 | −0.0837 | 0.4903 | 0.100* | |
C11 | 0.67809 (18) | 0.2618 (3) | 0.31346 (11) | 0.0414 (4) | |
C12 | 0.6924 (2) | 0.1568 (4) | 0.24589 (13) | 0.0578 (6) | |
H12A | 0.7608 | 0.1964 | 0.2187 | 0.087* | |
H12B | 0.6154 | 0.1577 | 0.2108 | 0.087* | |
H12C | 0.7105 | 0.0471 | 0.2637 | 0.087* | |
N1 | 0.87655 (17) | 0.5628 (3) | 0.37515 (10) | 0.0464 (4) | |
N2 | 0.7918 (2) | 0.6596 (3) | 0.37832 (11) | 0.0503 (4) | |
N3 | 0.7199 (3) | 0.7564 (4) | 0.37460 (16) | 0.0817 (8) | |
O1 | 0.90401 (13) | 0.53370 (18) | 0.50904 (8) | 0.0397 (3) | |
O2 | 0.71909 (12) | 0.3963 (2) | 0.59695 (8) | 0.0412 (3) | |
O3 | 0.7145 (3) | 0.2628 (4) | 0.70717 (15) | 0.0982 (9) | |
O4 | 0.69081 (12) | 0.1234 (2) | 0.50590 (8) | 0.0433 (3) | |
O5 | 0.80795 (16) | −0.0760 (2) | 0.55997 (12) | 0.0598 (5) | |
O6 | 0.77384 (13) | 0.24026 (19) | 0.36858 (8) | 0.0422 (3) | |
O7 | 0.59591 (15) | 0.3540 (3) | 0.31968 (9) | 0.0626 (5) | |
C21 | 0.41387 (18) | 0.1436 (3) | 0.92317 (11) | 0.0416 (4) | |
H21 | 0.4928 | 0.2051 | 0.9346 | 0.050* | |
C22 | 0.30575 (17) | 0.2605 (3) | 0.91584 (11) | 0.0375 (4) | |
H22 | 0.3172 | 0.3413 | 0.8749 | 0.045* | |
C23 | 0.29754 (16) | 0.3448 (2) | 0.99233 (11) | 0.0359 (4) | |
H23 | 0.3710 | 0.4168 | 1.0033 | 0.043* | |
C24 | 0.29594 (16) | 0.2255 (3) | 1.05760 (10) | 0.0357 (4) | |
H24 | 0.2162 | 0.1643 | 1.0527 | 0.043* | |
C25 | 0.40663 (17) | 0.1117 (3) | 1.05714 (10) | 0.0377 (4) | |
H25 | 0.4845 | 0.1765 | 1.0647 | 0.045* | |
C26 | 0.4212 (3) | 0.0465 (4) | 0.85091 (13) | 0.0602 (7) | |
H26A | 0.3481 | −0.0229 | 0.8421 | 0.090* | |
H26B | 0.4964 | −0.0195 | 0.8568 | 0.090* | |
H26C | 0.4238 | 0.1187 | 0.8068 | 0.090* | |
C27 | 0.1248 (2) | 0.2083 (3) | 0.82833 (13) | 0.0495 (5) | |
C28 | 0.0126 (2) | 0.1050 (4) | 0.81386 (14) | 0.0614 (7) | |
H28A | 0.0297 | 0.0167 | 0.7796 | 0.092* | |
H28B | −0.0568 | 0.1688 | 0.7896 | 0.092* | |
H28C | −0.0089 | 0.0617 | 0.8629 | 0.092* | |
C29 | 0.1931 (2) | 0.5885 (3) | 0.96060 (12) | 0.0452 (5) | |
C30 | 0.0707 (3) | 0.6710 (4) | 0.95600 (18) | 0.0709 (8) | |
H30A | 0.0169 | 0.6305 | 0.9114 | 0.106* | |
H30B | 0.0826 | 0.7865 | 0.9503 | 0.106* | |
H30C | 0.0320 | 0.6502 | 1.0032 | 0.106* | |
C31 | 0.24280 (19) | 0.2720 (3) | 1.18562 (11) | 0.0434 (4) | |
C32 | 0.2743 (2) | 0.3784 (4) | 1.25386 (13) | 0.0561 (6) | |
H32A | 0.2172 | 0.3572 | 1.2925 | 0.084* | |
H32B | 0.2669 | 0.4906 | 1.2376 | 0.084* | |
H32C | 0.3596 | 0.3571 | 1.2762 | 0.084* | |
N4 | 0.41111 (18) | −0.0085 (2) | 1.11835 (10) | 0.0470 (4) | |
N5 | 0.3216 (2) | −0.1029 (3) | 1.11095 (11) | 0.0528 (5) | |
N6 | 0.2492 (3) | −0.1971 (4) | 1.11125 (15) | 0.0801 (8) | |
O11 | 0.40255 (13) | 0.03261 (19) | 0.98530 (8) | 0.0410 (3) | |
O12 | 0.19169 (13) | 0.1727 (2) | 0.89577 (8) | 0.0432 (3) | |
O13 | 0.1555 (2) | 0.3078 (4) | 0.78532 (13) | 0.0936 (9) | |
O14 | 0.18610 (12) | 0.4389 (2) | 0.99016 (8) | 0.0433 (3) | |
O15 | 0.28619 (16) | 0.6426 (2) | 0.94021 (11) | 0.0557 (4) | |
O16 | 0.31026 (13) | 0.31544 (19) | 1.12799 (8) | 0.0413 (3) | |
O17 | 0.17042 (17) | 0.1639 (3) | 1.18030 (10) | 0.0650 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0342 (8) | 0.0473 (11) | 0.0391 (9) | −0.0012 (8) | −0.0033 (7) | 0.0073 (8) |
C2 | 0.0325 (8) | 0.0438 (10) | 0.0348 (8) | 0.0012 (7) | −0.0011 (6) | 0.0055 (8) |
C3 | 0.0282 (7) | 0.0405 (10) | 0.0378 (8) | 0.0003 (7) | 0.0023 (6) | 0.0029 (8) |
C4 | 0.0315 (8) | 0.0416 (10) | 0.0349 (8) | 0.0045 (7) | 0.0024 (6) | 0.0001 (7) |
C5 | 0.0363 (8) | 0.0413 (10) | 0.0363 (8) | 0.0037 (8) | 0.0043 (7) | 0.0036 (8) |
C6 | 0.0549 (12) | 0.0646 (14) | 0.0415 (11) | −0.0188 (12) | −0.0065 (9) | 0.0035 (11) |
C7 | 0.0521 (11) | 0.0508 (12) | 0.0428 (10) | −0.0074 (10) | 0.0110 (8) | 0.0014 (10) |
C8 | 0.0497 (11) | 0.0739 (16) | 0.0473 (11) | −0.0044 (12) | 0.0125 (9) | −0.0141 (12) |
C9 | 0.0471 (11) | 0.0529 (12) | 0.0378 (9) | −0.0100 (10) | 0.0082 (8) | 0.0036 (9) |
C10 | 0.0634 (14) | 0.082 (2) | 0.0540 (13) | −0.0317 (15) | 0.0043 (11) | 0.0134 (14) |
C11 | 0.0389 (9) | 0.0510 (11) | 0.0341 (9) | −0.0039 (9) | 0.0031 (7) | 0.0038 (8) |
C12 | 0.0637 (13) | 0.0681 (16) | 0.0407 (11) | 0.0003 (13) | 0.0015 (10) | −0.0112 (11) |
N1 | 0.0491 (9) | 0.0507 (10) | 0.0405 (8) | 0.0039 (8) | 0.0097 (7) | 0.0088 (8) |
N2 | 0.0583 (10) | 0.0529 (11) | 0.0393 (9) | 0.0056 (9) | 0.0027 (8) | 0.0089 (8) |
N3 | 0.0919 (18) | 0.0813 (18) | 0.0720 (15) | 0.0400 (16) | 0.0099 (13) | 0.0241 (15) |
O1 | 0.0408 (7) | 0.0404 (7) | 0.0372 (6) | −0.0002 (6) | 0.0007 (5) | 0.0034 (6) |
O2 | 0.0369 (6) | 0.0521 (8) | 0.0348 (6) | 0.0039 (6) | 0.0041 (5) | 0.0042 (6) |
O3 | 0.121 (2) | 0.0965 (18) | 0.0869 (15) | 0.0346 (16) | 0.0562 (15) | 0.0502 (15) |
O4 | 0.0335 (6) | 0.0507 (9) | 0.0451 (7) | −0.0065 (6) | 0.0022 (5) | 0.0034 (7) |
O5 | 0.0535 (9) | 0.0495 (10) | 0.0769 (12) | −0.0007 (8) | 0.0100 (8) | 0.0190 (9) |
O6 | 0.0401 (7) | 0.0479 (8) | 0.0379 (7) | 0.0068 (6) | 0.0011 (5) | −0.0060 (6) |
O7 | 0.0500 (8) | 0.0932 (15) | 0.0424 (8) | 0.0218 (10) | −0.0053 (6) | −0.0050 (9) |
C21 | 0.0408 (9) | 0.0487 (11) | 0.0358 (9) | 0.0048 (9) | 0.0063 (7) | 0.0021 (8) |
C22 | 0.0341 (8) | 0.0458 (11) | 0.0324 (8) | −0.0011 (8) | 0.0022 (6) | 0.0011 (8) |
C23 | 0.0299 (7) | 0.0418 (10) | 0.0357 (8) | −0.0001 (7) | 0.0017 (6) | −0.0010 (8) |
C24 | 0.0339 (8) | 0.0425 (10) | 0.0299 (8) | −0.0033 (7) | 0.0004 (6) | −0.0029 (7) |
C25 | 0.0372 (8) | 0.0422 (10) | 0.0326 (8) | 0.0000 (8) | −0.0009 (7) | 0.0004 (8) |
C26 | 0.0714 (15) | 0.0716 (16) | 0.0382 (10) | 0.0237 (14) | 0.0093 (10) | −0.0056 (11) |
C27 | 0.0492 (11) | 0.0590 (13) | 0.0379 (9) | 0.0007 (10) | −0.0054 (8) | 0.0001 (10) |
C28 | 0.0526 (12) | 0.0824 (19) | 0.0465 (12) | −0.0089 (13) | −0.0072 (10) | −0.0063 (13) |
C29 | 0.0470 (11) | 0.0518 (12) | 0.0359 (9) | 0.0116 (9) | −0.0002 (8) | 0.0003 (9) |
C30 | 0.0599 (14) | 0.081 (2) | 0.0705 (16) | 0.0317 (15) | 0.0029 (12) | 0.0121 (16) |
C31 | 0.0412 (9) | 0.0560 (12) | 0.0322 (8) | 0.0053 (9) | 0.0008 (7) | −0.0034 (9) |
C32 | 0.0566 (12) | 0.0692 (16) | 0.0416 (11) | 0.0088 (12) | 0.0018 (9) | −0.0143 (11) |
N4 | 0.0532 (10) | 0.0477 (10) | 0.0387 (8) | 0.0027 (8) | −0.0019 (7) | 0.0053 (8) |
N5 | 0.0726 (13) | 0.0503 (11) | 0.0365 (9) | −0.0029 (10) | 0.0105 (8) | 0.0004 (8) |
N6 | 0.112 (2) | 0.0714 (16) | 0.0595 (13) | −0.0353 (17) | 0.0188 (13) | 0.0004 (13) |
O11 | 0.0464 (7) | 0.0418 (7) | 0.0346 (6) | 0.0021 (6) | 0.0036 (5) | −0.0018 (6) |
O12 | 0.0402 (7) | 0.0537 (9) | 0.0343 (6) | −0.0069 (6) | −0.0024 (5) | 0.0000 (6) |
O13 | 0.0953 (16) | 0.1029 (19) | 0.0727 (13) | −0.0326 (15) | −0.0360 (12) | 0.0425 (14) |
O14 | 0.0340 (6) | 0.0515 (9) | 0.0441 (7) | 0.0052 (6) | 0.0033 (5) | 0.0025 (7) |
O15 | 0.0570 (9) | 0.0481 (9) | 0.0631 (10) | 0.0061 (8) | 0.0112 (8) | 0.0079 (8) |
O16 | 0.0424 (7) | 0.0469 (8) | 0.0338 (6) | −0.0023 (6) | 0.0010 (5) | −0.0063 (6) |
O17 | 0.0667 (10) | 0.0877 (14) | 0.0422 (8) | −0.0248 (11) | 0.0139 (7) | −0.0066 (9) |
C1—O1 | 1.444 (2) | C21—O11 | 1.441 (2) |
C1—C6 | 1.513 (3) | C21—C26 | 1.508 (3) |
C1—C2 | 1.520 (3) | C21—C22 | 1.521 (3) |
C1—H1 | 1.0000 | C21—H21 | 1.0000 |
C2—O2 | 1.449 (2) | C22—O12 | 1.448 (2) |
C2—C3 | 1.518 (3) | C22—C23 | 1.519 (3) |
C2—H2 | 1.0000 | C22—H22 | 1.0000 |
C3—O4 | 1.441 (2) | C23—O14 | 1.439 (2) |
C3—C4 | 1.516 (3) | C23—C24 | 1.514 (3) |
C3—H3 | 1.0000 | C23—H23 | 1.0000 |
C4—O6 | 1.436 (2) | C24—O16 | 1.433 (2) |
C4—C5 | 1.529 (3) | C24—C25 | 1.532 (3) |
C4—H4 | 1.0000 | C24—H24 | 1.0000 |
C5—O1 | 1.413 (2) | C25—O11 | 1.413 (2) |
C5—N1 | 1.464 (3) | C25—N4 | 1.463 (3) |
C5—H5 | 1.0000 | C25—H25 | 1.0000 |
C6—H6A | 0.9800 | C26—H26A | 0.9800 |
C6—H6B | 0.9800 | C26—H26B | 0.9800 |
C6—H6C | 0.9800 | C26—H26C | 0.9800 |
C7—O3 | 1.187 (3) | C27—O13 | 1.191 (3) |
C7—O2 | 1.346 (2) | C27—O12 | 1.346 (3) |
C7—C8 | 1.488 (4) | C27—C28 | 1.490 (4) |
C8—H8A | 0.9800 | C28—H28A | 0.9800 |
C8—H8B | 0.9800 | C28—H28B | 0.9800 |
C8—H8C | 0.9800 | C28—H28C | 0.9800 |
C9—O5 | 1.194 (3) | C29—O15 | 1.195 (3) |
C9—O4 | 1.354 (3) | C29—O14 | 1.357 (3) |
C9—C10 | 1.489 (3) | C29—C30 | 1.490 (3) |
C10—H10A | 0.9800 | C30—H30A | 0.9800 |
C10—H10B | 0.9800 | C30—H30B | 0.9800 |
C10—H10C | 0.9800 | C30—H30C | 0.9800 |
C11—O7 | 1.192 (3) | C31—O17 | 1.194 (3) |
C11—O6 | 1.348 (2) | C31—O16 | 1.356 (3) |
C11—C12 | 1.491 (3) | C31—C32 | 1.495 (3) |
C12—H12A | 0.9800 | C32—H32A | 0.9800 |
C12—H12B | 0.9800 | C32—H32B | 0.9800 |
C12—H12C | 0.9800 | C32—H32C | 0.9800 |
N1—N2 | 1.230 (3) | N4—N5 | 1.246 (3) |
N2—N3 | 1.120 (3) | N5—N6 | 1.112 (3) |
O1—C1—C6 | 107.60 (18) | O11—C21—C26 | 107.4 (2) |
O1—C1—C2 | 110.40 (14) | O11—C21—C22 | 110.38 (15) |
C6—C1—C2 | 113.00 (17) | C26—C21—C22 | 112.67 (17) |
O1—C1—H1 | 108.6 | O11—C21—H21 | 108.8 |
C6—C1—H1 | 108.6 | C26—C21—H21 | 108.8 |
C2—C1—H1 | 108.6 | C22—C21—H21 | 108.8 |
O2—C2—C3 | 108.70 (14) | O12—C22—C23 | 108.46 (14) |
O2—C2—C1 | 108.46 (17) | O12—C22—C21 | 108.98 (17) |
C3—C2—C1 | 110.69 (15) | C23—C22—C21 | 110.00 (15) |
O2—C2—H2 | 109.7 | O12—C22—H22 | 109.8 |
C3—C2—H2 | 109.7 | C23—C22—H22 | 109.8 |
C1—C2—H2 | 109.7 | C21—C22—H22 | 109.8 |
O4—C3—C4 | 107.35 (14) | O14—C23—C24 | 107.51 (14) |
O4—C3—C2 | 111.26 (14) | O14—C23—C22 | 111.06 (14) |
C4—C3—C2 | 111.19 (17) | C24—C23—C22 | 111.24 (17) |
O4—C3—H3 | 109.0 | O14—C23—H23 | 109.0 |
C4—C3—H3 | 109.0 | C24—C23—H23 | 109.0 |
C2—C3—H3 | 109.0 | C22—C23—H23 | 109.0 |
O6—C4—C3 | 107.19 (16) | O16—C24—C23 | 106.88 (17) |
O6—C4—C5 | 107.86 (14) | O16—C24—C25 | 108.53 (14) |
C3—C4—C5 | 108.81 (14) | C23—C24—C25 | 109.33 (14) |
O6—C4—H4 | 110.9 | O16—C24—H24 | 110.7 |
C3—C4—H4 | 110.9 | C23—C24—H24 | 110.7 |
C5—C4—H4 | 110.9 | C25—C24—H24 | 110.7 |
O1—C5—N1 | 108.45 (17) | O11—C25—N4 | 108.77 (17) |
O1—C5—C4 | 109.77 (14) | O11—C25—C24 | 110.24 (14) |
N1—C5—C4 | 112.65 (16) | N4—C25—C24 | 112.70 (16) |
O1—C5—H5 | 108.6 | O11—C25—H25 | 108.3 |
N1—C5—H5 | 108.6 | N4—C25—H25 | 108.3 |
C4—C5—H5 | 108.6 | C24—C25—H25 | 108.3 |
C1—C6—H6A | 109.5 | C21—C26—H26A | 109.5 |
C1—C6—H6B | 109.5 | C21—C26—H26B | 109.5 |
H6A—C6—H6B | 109.5 | H26A—C26—H26B | 109.5 |
C1—C6—H6C | 109.5 | C21—C26—H26C | 109.5 |
H6A—C6—H6C | 109.5 | H26A—C26—H26C | 109.5 |
H6B—C6—H6C | 109.5 | H26B—C26—H26C | 109.5 |
O3—C7—O2 | 123.0 (2) | O13—C27—O12 | 122.9 (2) |
O3—C7—C8 | 125.2 (2) | O13—C27—C28 | 125.2 (2) |
O2—C7—C8 | 111.7 (2) | O12—C27—C28 | 111.9 (2) |
C7—C8—H8A | 109.5 | C27—C28—H28A | 109.5 |
C7—C8—H8B | 109.5 | C27—C28—H28B | 109.5 |
H8A—C8—H8B | 109.5 | H28A—C28—H28B | 109.5 |
C7—C8—H8C | 109.5 | C27—C28—H28C | 109.5 |
H8A—C8—H8C | 109.5 | H28A—C28—H28C | 109.5 |
H8B—C8—H8C | 109.5 | H28B—C28—H28C | 109.5 |
O5—C9—O4 | 122.89 (19) | O15—C29—O14 | 123.0 (2) |
O5—C9—C10 | 125.7 (2) | O15—C29—C30 | 125.9 (2) |
O4—C9—C10 | 111.4 (2) | O14—C29—C30 | 111.1 (2) |
C9—C10—H10A | 109.5 | C29—C30—H30A | 109.5 |
C9—C10—H10B | 109.5 | C29—C30—H30B | 109.5 |
H10A—C10—H10B | 109.5 | H30A—C30—H30B | 109.5 |
C9—C10—H10C | 109.5 | C29—C30—H30C | 109.5 |
H10A—C10—H10C | 109.5 | H30A—C30—H30C | 109.5 |
H10B—C10—H10C | 109.5 | H30B—C30—H30C | 109.5 |
O7—C11—O6 | 123.14 (19) | O17—C31—O16 | 123.24 (19) |
O7—C11—C12 | 126.6 (2) | O17—C31—C32 | 127.1 (2) |
O6—C11—C12 | 110.29 (19) | O16—C31—C32 | 109.6 (2) |
C11—C12—H12A | 109.5 | C31—C32—H32A | 109.5 |
C11—C12—H12B | 109.5 | C31—C32—H32B | 109.5 |
H12A—C12—H12B | 109.5 | H32A—C32—H32B | 109.5 |
C11—C12—H12C | 109.5 | C31—C32—H32C | 109.5 |
H12A—C12—H12C | 109.5 | H32A—C32—H32C | 109.5 |
H12B—C12—H12C | 109.5 | H32B—C32—H32C | 109.5 |
N2—N1—C5 | 114.10 (17) | N5—N4—C25 | 113.28 (17) |
N3—N2—N1 | 172.2 (3) | N6—N5—N4 | 171.7 (3) |
C5—O1—C1 | 112.36 (16) | C25—O11—C21 | 111.66 (16) |
C7—O2—C2 | 117.49 (17) | C27—O12—C22 | 117.67 (18) |
C9—O4—C3 | 115.92 (15) | C29—O14—C23 | 115.56 (15) |
C11—O6—C4 | 118.72 (16) | C31—O16—C24 | 118.57 (16) |