Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805014030/bt6660sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805014030/bt6660Isup2.hkl |
CCDC reference: 274341
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.
C6H13NO2·C6H14NO2+·C6H2N3O7− | Z = 2 |
Mr = 491.46 | F(000) = 520 |
Triclinic, P1 | Dx = 1.306 Mg m−3 Dm = 1.297 Mg m−3 Dm measured by flotation in a mixture of carbon tetracholride and xylene |
a = 7.1470 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.8540 (8) Å | Cell parameters from 25 reflections |
c = 15.456 (1) Å | θ = 10.4–13.9° |
α = 106.45 (2)° | µ = 0.11 mm−1 |
β = 95.17 (1)° | T = 293 K |
γ = 91.02 (2)° | Plate, yellow |
V = 1249.5 (2) Å3 | 0.25 × 0.15 × 0.12 mm |
Nonius MACH3 sealed tube diffractometer | 3495 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.015 |
Graphite monochromator | θmax = 25.0°, θmin = 2.6° |
ω–2θ scans | h = −1→8 |
Absorption correction: ψ scan (North et al., 1968) | k = −14→14 |
Tmin = 0.981, Tmax = 0.987 | l = −18→18 |
5538 measured reflections | 3 standard reflections every 60 min |
4392 independent reflections | intensity decay: 1% |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0871P)2 + 0.3632P] where P = (Fo2 + 2Fc2)/3 |
4392 reflections | (Δ/σ)max < 0.001 |
609 parameters | Δρmax = 0.38 e Å−3 |
6 restraints | Δρmin = −0.50 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 | 0.6176 (7) | 0.7671 (4) | 0.8035 (3) | 0.0417 (11) | |
C2 | 0.4548 (7) | 0.7822 (4) | 0.8537 (3) | 0.0433 (11) | |
C3 | 0.4338 (7) | 0.7357 (5) | 0.9250 (3) | 0.0462 (12) | |
H3 | 0.3256 | 0.7477 | 0.9551 | 0.055* | |
C4 | 0.5764 (8) | 0.6711 (5) | 0.9507 (3) | 0.0474 (13) | |
C5 | 0.7364 (8) | 0.6505 (4) | 0.9058 (3) | 0.0457 (12) | |
H5 | 0.8306 | 0.6065 | 0.9240 | 0.055* | |
C6 | 0.7554 (7) | 0.6956 (4) | 0.8337 (3) | 0.0412 (11) | |
N3 | 0.3022 (7) | 0.8483 (5) | 0.8289 (3) | 0.0579 (12) | |
N1 | 0.9216 (7) | 0.6659 (5) | 0.7873 (3) | 0.0581 (12) | |
N2 | 0.5577 (9) | 0.6264 (5) | 1.0273 (3) | 0.0649 (14) | |
O1 | 0.6372 (5) | 0.8156 (4) | 0.7423 (2) | 0.0559 (10) | |
O7 | 0.2739 (7) | 0.8528 (6) | 0.7507 (3) | 0.0908 (17) | |
O6 | 0.2046 (7) | 0.8986 (5) | 0.8866 (3) | 0.0858 (15) | |
O5 | 0.4181 (8) | 0.6490 (5) | 1.0677 (3) | 0.0853 (15) | |
O4 | 0.6892 (9) | 0.5737 (6) | 1.0520 (4) | 0.1029 (19) | |
O3 | 1.0540 (7) | 0.6235 (5) | 0.8222 (4) | 0.0882 (15) | |
O2 | 0.9304 (8) | 0.6832 (7) | 0.7137 (4) | 0.116 (2) | |
C11 | 0.6452 (7) | 0.8929 (4) | 0.1905 (3) | 0.0421 (11) | |
C12 | 0.5065 (7) | 0.9652 (5) | 0.1574 (3) | 0.0451 (12) | |
C13 | 0.5272 (8) | 1.0089 (5) | 0.0865 (3) | 0.0480 (12) | |
H13 | 0.4326 | 1.0523 | 0.0679 | 0.058* | |
C14 | 0.6860 (7) | 0.9897 (5) | 0.0421 (3) | 0.0438 (11) | |
C15 | 0.8262 (8) | 0.9214 (5) | 0.0663 (3) | 0.0486 (12) | |
H15 | 0.9312 | 0.9057 | 0.0341 | 0.058* | |
C16 | 0.8075 (7) | 0.8781 (5) | 0.1374 (3) | 0.0456 (12) | |
N11 | 0.3374 (7) | 0.9942 (5) | 0.2041 (4) | 0.0627 (13) | |
N12 | 0.7062 (8) | 1.0359 (5) | −0.0342 (3) | 0.0594 (13) | |
N13 | 0.9586 (7) | 0.8070 (4) | 0.1595 (3) | 0.0580 (12) | |
O11 | 0.6263 (6) | 0.8484 (4) | 0.2529 (2) | 0.0551 (10) | |
O12 | 0.3182 (8) | 0.9669 (7) | 0.2719 (4) | 0.117 (2) | |
O13 | 0.2168 (8) | 1.0415 (7) | 0.1701 (5) | 0.119 (2) | |
O14 | 0.5792 (8) | 1.0890 (5) | −0.0587 (4) | 0.0920 (17) | |
O15 | 0.8502 (8) | 1.0184 (5) | −0.0720 (3) | 0.0886 (16) | |
O16 | 1.0580 (7) | 0.7590 (5) | 0.1010 (3) | 0.0888 (16) | |
O17 | 0.9861 (7) | 0.8032 (5) | 0.2383 (3) | 0.0820 (15) | |
C21 | 0.6535 (6) | 0.0380 (4) | 0.6472 (3) | 0.0403 (10) | |
C22 | 0.7999 (6) | 0.0708 (4) | 0.7294 (3) | 0.0401 (10) | |
H22 | 0.7342 | 0.0876 | 0.7844 | 0.048* | |
C23 | 0.9235 (9) | 0.1801 (5) | 0.7332 (4) | 0.0566 (14) | |
H23A | 1.0174 | 0.1566 | 0.6907 | 0.068* | |
H23B | 0.8453 | 0.2358 | 0.7133 | 0.068* | |
C24 | 1.0223 (12) | 0.2413 (6) | 0.8256 (4) | 0.080 (2) | |
H24 | 1.0679 | 0.1828 | 0.8554 | 0.096* | |
C25 | 0.8706 (18) | 0.3188 (11) | 0.8823 (8) | 0.154 (3) | |
H25A | 0.7651 | 0.3270 | 0.8419 | 0.231* | |
H25B | 0.9262 | 0.3952 | 0.9145 | 0.231* | |
H25C | 0.8291 | 0.2807 | 0.9249 | 0.231* | |
C26 | 1.181 (2) | 0.3242 (10) | 0.8235 (8) | 0.154 (3) | |
H26A | 1.2548 | 0.2877 | 0.7751 | 0.231* | |
H26B | 1.2586 | 0.3432 | 0.8802 | 0.231* | |
H26C | 1.1314 | 0.3949 | 0.8140 | 0.231* | |
N21 | 0.9190 (6) | −0.0321 (4) | 0.7267 (3) | 0.0456 (10) | |
H21A | 0.8456 | −0.0957 | 0.7213 | 0.068* | |
H21B | 0.9958 | −0.0172 | 0.7776 | 0.068* | |
H21C | 0.9865 | −0.0449 | 0.6795 | 0.068* | |
O21B | 0.5289 (6) | 0.1114 (3) | 0.6490 (3) | 0.0684 (11) | |
O21A | 0.6664 (5) | −0.0557 (3) | 0.5861 (2) | 0.0454 (8) | |
C31 | 0.0903 (7) | 0.6128 (4) | 0.3338 (3) | 0.0439 (11) | |
C32 | 0.2107 (6) | 0.5778 (4) | 0.2540 (3) | 0.0405 (10) | |
H32 | 0.1276 | 0.5614 | 0.1975 | 0.049* | |
C33 | 0.3199 (8) | 0.4691 (5) | 0.2533 (4) | 0.0519 (13) | |
H33A | 0.4177 | 0.4900 | 0.3036 | 0.062* | |
H33B | 0.2353 | 0.4106 | 0.2639 | 0.062* | |
C34 | 0.4100 (17) | 0.4133 (9) | 0.1681 (6) | 0.127 (2) | |
H34 | 0.4761 | 0.4773 | 0.1530 | 0.153* | |
C35 | 0.2847 (17) | 0.3577 (9) | 0.0917 (6) | 0.127 (2) | |
H35A | 0.2075 | 0.2992 | 0.1054 | 0.191* | |
H35B | 0.3547 | 0.3209 | 0.0419 | 0.191* | |
H35C | 0.2064 | 0.4151 | 0.0757 | 0.191* | |
C36 | 0.5588 (17) | 0.3284 (9) | 0.1826 (6) | 0.127 (2) | |
H36A | 0.4990 | 0.2601 | 0.1918 | 0.191* | |
H36B | 0.6437 | 0.3665 | 0.2350 | 0.191* | |
H36C | 0.6274 | 0.3051 | 0.1303 | 0.191* | |
N31 | 0.3424 (6) | 0.6795 (4) | 0.2591 (3) | 0.0462 (10) | |
H31A | 0.4260 | 0.6909 | 0.3074 | 0.069* | |
H31B | 0.2776 | 0.7440 | 0.2638 | 0.069* | |
H31C | 0.4020 | 0.6641 | 0.2092 | 0.069* | |
O31B | −0.0397 (6) | 0.5388 (3) | 0.3302 (3) | 0.0732 (12) | |
O31A | 0.1296 (5) | 0.7062 (3) | 0.3954 (2) | 0.0461 (8) | |
C41 | 1.1462 (6) | 0.0021 (4) | 0.5153 (3) | 0.0409 (10) | |
C42 | 0.9944 (6) | 0.0011 (4) | 0.4392 (3) | 0.0372 (10) | |
H42 | 1.0547 | −0.0028 | 0.3840 | 0.045* | |
C43 | 0.8846 (8) | 0.1146 (4) | 0.4642 (3) | 0.0446 (12) | |
H43A | 0.8015 | 0.1089 | 0.5092 | 0.053* | |
H43B | 0.9736 | 0.1803 | 0.4923 | 0.053* | |
C45 | 0.8862 (12) | 0.1732 (7) | 0.3202 (5) | 0.086 (2) | |
H45A | 0.8071 | 0.1836 | 0.2697 | 0.129* | |
H45B | 0.9694 | 0.1108 | 0.2990 | 0.129* | |
H45C | 0.9586 | 0.2449 | 0.3500 | 0.129* | |
C44 | 0.7669 (8) | 0.1424 (5) | 0.3856 (4) | 0.0567 (13) | |
H44 | 0.6904 | 0.0713 | 0.3525 | 0.068* | |
C46 | 0.6333 (10) | 0.2383 (6) | 0.4227 (5) | 0.082 (2) | |
H46A | 0.7042 | 0.3085 | 0.4575 | 0.123* | |
H46B | 0.5531 | 0.2127 | 0.4607 | 0.123* | |
H46C | 0.5579 | 0.2545 | 0.3733 | 0.123* | |
N41 | 0.8670 (6) | −0.1047 (4) | 0.4223 (3) | 0.0399 (9) | |
H41A | 0.9346 | −0.1667 | 0.4233 | 0.060* | |
H41B | 0.8016 | −0.1180 | 0.3683 | 0.060* | |
H41C | 0.7883 | −0.0929 | 0.4652 | 0.060* | |
O41A | 1.1312 (5) | −0.0613 (3) | 0.5647 (2) | 0.0483 (9) | |
O41B | 1.2785 (6) | 0.0786 (4) | 0.5222 (3) | 0.0718 (12) | |
H41D | 1.3615 | 0.0730 | 0.5608 | 0.108* | |
C51 | 0.6333 (7) | 0.6409 (4) | 0.4631 (3) | 0.0418 (10) | |
C52 | 0.5207 (6) | 0.6460 (4) | 0.5426 (3) | 0.0368 (9) | |
H52 | 0.6083 | 0.6518 | 0.5964 | 0.044* | |
C53 | 0.3900 (7) | 0.5363 (4) | 0.5256 (3) | 0.0438 (11) | |
H53A | 0.2832 | 0.5420 | 0.4839 | 0.053* | |
H53B | 0.4571 | 0.4677 | 0.4962 | 0.053* | |
C54 | 0.3170 (9) | 0.5167 (5) | 0.6097 (4) | 0.0586 (14) | |
H54 | 0.2761 | 0.5919 | 0.6471 | 0.070* | |
C55 | 0.4686 (13) | 0.4722 (7) | 0.6655 (5) | 0.093 (3) | |
H55A | 0.4835 | 0.3899 | 0.6377 | 0.139* | |
H55B | 0.4328 | 0.4833 | 0.7257 | 0.139* | |
H55C | 0.5853 | 0.5152 | 0.6685 | 0.139* | |
C56 | 0.1461 (11) | 0.4290 (7) | 0.5805 (6) | 0.095 (2) | |
H56A | 0.0498 | 0.4603 | 0.5478 | 0.142* | |
H56B | 0.0984 | 0.4162 | 0.6333 | 0.142* | |
H56C | 0.1834 | 0.3556 | 0.5424 | 0.142* | |
N51 | 0.4088 (6) | 0.7542 (3) | 0.5598 (3) | 0.0417 (9) | |
H51A | 0.4820 | 0.8154 | 0.5591 | 0.063* | |
H51B | 0.3647 | 0.7679 | 0.6137 | 0.063* | |
H51C | 0.3131 | 0.7438 | 0.5169 | 0.063* | |
O51B | 0.7605 (6) | 0.5641 (4) | 0.4548 (3) | 0.0674 (11) | |
H51D | 0.8161 | 0.5631 | 0.4104 | 0.101* | |
O51A | 0.6049 (5) | 0.7054 (3) | 0.4153 (2) | 0.0490 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.048 (3) | 0.045 (3) | 0.031 (2) | −0.001 (2) | 0.001 (2) | 0.011 (2) |
C2 | 0.044 (3) | 0.050 (3) | 0.037 (3) | 0.007 (2) | 0.009 (2) | 0.013 (2) |
C3 | 0.048 (3) | 0.057 (3) | 0.034 (2) | 0.005 (2) | 0.010 (2) | 0.012 (2) |
C4 | 0.063 (4) | 0.050 (3) | 0.034 (2) | 0.007 (3) | 0.006 (2) | 0.018 (2) |
C5 | 0.049 (3) | 0.049 (3) | 0.040 (3) | 0.005 (2) | −0.003 (2) | 0.017 (2) |
C6 | 0.037 (3) | 0.048 (3) | 0.040 (3) | 0.003 (2) | 0.007 (2) | 0.013 (2) |
N3 | 0.052 (3) | 0.073 (3) | 0.055 (3) | 0.021 (2) | 0.013 (2) | 0.025 (2) |
N1 | 0.046 (3) | 0.075 (3) | 0.055 (3) | 0.010 (2) | 0.008 (2) | 0.021 (2) |
N2 | 0.087 (4) | 0.067 (3) | 0.049 (3) | 0.007 (3) | 0.011 (3) | 0.031 (2) |
O1 | 0.054 (2) | 0.074 (3) | 0.050 (2) | −0.0001 (19) | 0.0081 (17) | 0.0334 (19) |
O7 | 0.076 (3) | 0.144 (5) | 0.071 (3) | 0.053 (3) | 0.017 (2) | 0.056 (3) |
O6 | 0.086 (4) | 0.103 (4) | 0.075 (3) | 0.048 (3) | 0.028 (3) | 0.028 (3) |
O5 | 0.108 (4) | 0.105 (4) | 0.063 (3) | 0.023 (3) | 0.044 (3) | 0.045 (3) |
O4 | 0.109 (4) | 0.139 (5) | 0.094 (4) | 0.033 (4) | 0.014 (3) | 0.084 (4) |
O3 | 0.058 (3) | 0.123 (4) | 0.095 (4) | 0.026 (3) | 0.015 (3) | 0.048 (3) |
O2 | 0.090 (4) | 0.202 (7) | 0.093 (4) | 0.067 (4) | 0.052 (3) | 0.083 (4) |
C11 | 0.038 (3) | 0.047 (3) | 0.039 (3) | −0.006 (2) | 0.000 (2) | 0.011 (2) |
C12 | 0.038 (3) | 0.056 (3) | 0.040 (3) | 0.005 (2) | 0.001 (2) | 0.011 (2) |
C13 | 0.052 (3) | 0.051 (3) | 0.043 (3) | 0.002 (2) | −0.003 (2) | 0.018 (2) |
C14 | 0.049 (3) | 0.052 (3) | 0.035 (2) | 0.005 (2) | 0.006 (2) | 0.018 (2) |
C15 | 0.049 (3) | 0.062 (3) | 0.033 (3) | 0.007 (3) | 0.005 (2) | 0.011 (2) |
C16 | 0.045 (3) | 0.054 (3) | 0.037 (3) | 0.008 (2) | −0.003 (2) | 0.014 (2) |
N11 | 0.043 (3) | 0.084 (4) | 0.068 (3) | 0.006 (3) | 0.012 (2) | 0.029 (3) |
N12 | 0.069 (3) | 0.074 (3) | 0.043 (3) | 0.014 (3) | 0.011 (2) | 0.026 (2) |
N13 | 0.061 (3) | 0.068 (3) | 0.047 (3) | 0.020 (3) | 0.004 (2) | 0.020 (2) |
O11 | 0.059 (2) | 0.072 (2) | 0.043 (2) | −0.0063 (19) | −0.0005 (17) | 0.0337 (18) |
O12 | 0.093 (4) | 0.192 (7) | 0.107 (4) | 0.057 (4) | 0.062 (4) | 0.091 (5) |
O13 | 0.070 (3) | 0.186 (6) | 0.140 (5) | 0.060 (4) | 0.038 (3) | 0.098 (5) |
O14 | 0.098 (4) | 0.118 (4) | 0.091 (4) | 0.038 (3) | 0.021 (3) | 0.075 (3) |
O15 | 0.097 (4) | 0.127 (4) | 0.067 (3) | 0.032 (3) | 0.036 (3) | 0.058 (3) |
O16 | 0.086 (4) | 0.124 (4) | 0.065 (3) | 0.058 (3) | 0.024 (3) | 0.034 (3) |
O17 | 0.089 (3) | 0.121 (4) | 0.050 (2) | 0.047 (3) | 0.006 (2) | 0.044 (2) |
C21 | 0.040 (2) | 0.045 (3) | 0.038 (2) | −0.002 (2) | 0.0003 (19) | 0.015 (2) |
C22 | 0.047 (3) | 0.045 (2) | 0.029 (2) | 0.002 (2) | −0.0008 (19) | 0.0134 (18) |
C23 | 0.067 (4) | 0.056 (3) | 0.045 (3) | −0.011 (3) | −0.010 (3) | 0.019 (2) |
C24 | 0.112 (6) | 0.065 (4) | 0.055 (3) | −0.027 (4) | −0.018 (4) | 0.013 (3) |
C25 | 0.198 (9) | 0.133 (6) | 0.114 (6) | −0.063 (6) | −0.014 (6) | 0.021 (5) |
C26 | 0.198 (9) | 0.133 (6) | 0.114 (6) | −0.063 (6) | −0.014 (6) | 0.021 (5) |
N21 | 0.040 (2) | 0.059 (3) | 0.043 (2) | 0.0047 (19) | 0.0021 (18) | 0.0242 (19) |
O21B | 0.057 (2) | 0.061 (2) | 0.075 (3) | 0.016 (2) | −0.0179 (19) | 0.0057 (19) |
O21A | 0.053 (2) | 0.0459 (19) | 0.0355 (17) | −0.0029 (16) | 0.0047 (15) | 0.0096 (16) |
C31 | 0.045 (3) | 0.049 (3) | 0.042 (3) | 0.013 (2) | 0.011 (2) | 0.017 (2) |
C32 | 0.041 (2) | 0.044 (2) | 0.039 (2) | 0.005 (2) | 0.0077 (19) | 0.0144 (19) |
C33 | 0.064 (3) | 0.047 (3) | 0.048 (3) | 0.009 (3) | 0.015 (3) | 0.016 (2) |
C34 | 0.178 (6) | 0.117 (4) | 0.082 (3) | 0.084 (4) | 0.024 (3) | 0.014 (3) |
C35 | 0.178 (6) | 0.117 (4) | 0.082 (3) | 0.084 (4) | 0.024 (3) | 0.014 (3) |
C36 | 0.178 (6) | 0.117 (4) | 0.082 (3) | 0.084 (4) | 0.024 (3) | 0.014 (3) |
N31 | 0.054 (3) | 0.052 (2) | 0.040 (2) | 0.008 (2) | 0.0100 (19) | 0.0244 (18) |
O31B | 0.072 (3) | 0.060 (2) | 0.081 (3) | −0.017 (2) | 0.039 (2) | 0.002 (2) |
O31A | 0.053 (2) | 0.0490 (19) | 0.0353 (17) | 0.0091 (16) | 0.0070 (15) | 0.0084 (15) |
C41 | 0.037 (2) | 0.044 (2) | 0.044 (3) | 0.007 (2) | 0.0079 (19) | 0.015 (2) |
C42 | 0.038 (2) | 0.046 (2) | 0.033 (2) | 0.003 (2) | 0.0043 (18) | 0.0194 (19) |
C43 | 0.052 (3) | 0.043 (3) | 0.041 (3) | 0.003 (2) | 0.003 (2) | 0.016 (2) |
C45 | 0.110 (6) | 0.102 (5) | 0.070 (4) | 0.041 (5) | 0.029 (4) | 0.054 (4) |
C44 | 0.065 (3) | 0.048 (3) | 0.058 (3) | 0.014 (2) | −0.002 (3) | 0.018 (2) |
C46 | 0.082 (5) | 0.072 (4) | 0.095 (5) | 0.035 (4) | 0.012 (4) | 0.028 (4) |
N41 | 0.041 (2) | 0.043 (2) | 0.038 (2) | 0.0052 (17) | 0.0057 (17) | 0.0153 (17) |
O41A | 0.053 (2) | 0.054 (2) | 0.0438 (19) | 0.0085 (16) | 0.0013 (15) | 0.0244 (17) |
O41B | 0.056 (2) | 0.083 (3) | 0.085 (3) | −0.022 (2) | −0.021 (2) | 0.048 (2) |
C51 | 0.044 (3) | 0.040 (2) | 0.044 (2) | −0.003 (2) | 0.005 (2) | 0.017 (2) |
C52 | 0.041 (2) | 0.037 (2) | 0.035 (2) | 0.0043 (19) | 0.0048 (19) | 0.0153 (18) |
C53 | 0.052 (3) | 0.038 (3) | 0.043 (3) | −0.003 (2) | 0.006 (2) | 0.013 (2) |
C54 | 0.073 (4) | 0.052 (3) | 0.055 (3) | −0.005 (3) | 0.021 (3) | 0.016 (2) |
C55 | 0.134 (7) | 0.087 (5) | 0.065 (4) | −0.035 (5) | −0.013 (4) | 0.042 (4) |
C56 | 0.090 (5) | 0.092 (5) | 0.108 (6) | −0.033 (4) | 0.018 (4) | 0.039 (5) |
N51 | 0.046 (2) | 0.039 (2) | 0.043 (2) | 0.0025 (18) | 0.0060 (18) | 0.0151 (17) |
O51B | 0.066 (2) | 0.074 (3) | 0.082 (3) | 0.030 (2) | 0.041 (2) | 0.044 (2) |
O51A | 0.055 (2) | 0.053 (2) | 0.046 (2) | 0.0016 (17) | 0.0050 (16) | 0.0260 (17) |
C1—O1 | 1.253 (6) | C32—C33 | 1.517 (7) |
C1—C6 | 1.442 (7) | C32—H32 | 0.9800 |
C1—C2 | 1.442 (7) | C33—C34 | 1.503 (10) |
C2—C3 | 1.382 (7) | C33—H33A | 0.9700 |
C2—N3 | 1.441 (7) | C33—H33B | 0.9700 |
C3—C4 | 1.382 (8) | C34—C35 | 1.406 (15) |
C3—H3 | 0.9300 | C34—C36 | 1.522 (12) |
C4—C5 | 1.380 (7) | C34—H34 | 0.9800 |
C4—N2 | 1.443 (7) | C35—H35A | 0.9600 |
C5—C6 | 1.382 (7) | C35—H35B | 0.9600 |
C5—H5 | 0.9300 | C35—H35C | 0.9600 |
C6—N1 | 1.441 (7) | C36—H36A | 0.9600 |
N3—O6 | 1.210 (6) | C36—H36B | 0.9600 |
N3—O7 | 1.224 (6) | C36—H36C | 0.9600 |
N1—O2 | 1.218 (7) | N31—H31A | 0.8900 |
N1—O3 | 1.231 (7) | N31—H31B | 0.8900 |
N2—O5 | 1.219 (7) | N31—H31C | 0.8900 |
N2—O4 | 1.228 (7) | C41—O41A | 1.223 (6) |
C11—O11 | 1.239 (6) | C41—O41B | 1.275 (6) |
C11—C16 | 1.464 (7) | C41—C42 | 1.524 (6) |
C11—C12 | 1.472 (7) | C42—N41 | 1.484 (6) |
C12—C13 | 1.355 (7) | C42—C43 | 1.541 (7) |
C12—N11 | 1.461 (7) | C42—H42 | 0.9800 |
C13—C14 | 1.369 (7) | C43—C44 | 1.532 (7) |
C13—H13 | 0.9300 | C43—H43A | 0.9700 |
C14—C15 | 1.390 (8) | C43—H43B | 0.9700 |
C14—N12 | 1.450 (6) | C45—C44 | 1.493 (9) |
C15—C16 | 1.355 (7) | C45—H45A | 0.9600 |
C15—H15 | 0.9300 | C45—H45B | 0.9600 |
C16—N13 | 1.456 (7) | C45—H45C | 0.9600 |
N11—O13 | 1.198 (7) | C44—C46 | 1.517 (8) |
N11—O12 | 1.199 (7) | C44—H44 | 0.9800 |
N12—O14 | 1.207 (7) | C46—H46A | 0.9600 |
N12—O15 | 1.222 (7) | C46—H46B | 0.9600 |
N13—O16 | 1.218 (6) | C46—H46C | 0.9600 |
N13—O17 | 1.229 (6) | N41—H41A | 0.8900 |
C21—O21A | 1.249 (6) | N41—H41B | 0.8900 |
C21—O21B | 1.253 (6) | N41—H41C | 0.8900 |
C21—C22 | 1.525 (6) | O41B—H41D | 0.8200 |
C22—N21 | 1.493 (6) | C51—O51A | 1.212 (6) |
C22—C23 | 1.540 (7) | C51—O51B | 1.286 (6) |
C22—H22 | 0.9800 | C51—C52 | 1.516 (6) |
C23—C24 | 1.510 (8) | C52—N51 | 1.496 (6) |
C23—H23A | 0.9700 | C52—C53 | 1.534 (6) |
C23—H23B | 0.9700 | C52—H52 | 0.9800 |
C24—C26 | 1.495 (13) | C53—C54 | 1.518 (7) |
C24—C25 | 1.594 (15) | C53—H53A | 0.9700 |
C24—H24 | 0.9800 | C53—H53B | 0.9700 |
C25—H25A | 0.9600 | C54—C55 | 1.518 (10) |
C25—H25B | 0.9600 | C54—C56 | 1.539 (9) |
C25—H25C | 0.9600 | C54—H54 | 0.9800 |
C26—H26A | 0.9600 | C55—H55A | 0.9600 |
C26—H26B | 0.9600 | C55—H55B | 0.9600 |
C26—H26C | 0.9600 | C55—H55C | 0.9600 |
N21—H21A | 0.8900 | C56—H56A | 0.9600 |
N21—H21B | 0.8900 | C56—H56B | 0.9600 |
N21—H21C | 0.8900 | C56—H56C | 0.9600 |
C31—O31A | 1.247 (6) | N51—H51A | 0.8900 |
C31—O31B | 1.253 (6) | N51—H51B | 0.8900 |
C31—C32 | 1.532 (6) | N51—H51C | 0.8900 |
C32—N31 | 1.496 (6) | O51B—H51D | 0.8200 |
O1—C1—C6 | 124.5 (5) | C32—C33—H33B | 108.2 |
O1—C1—C2 | 122.5 (5) | H33A—C33—H33B | 107.4 |
C6—C1—C2 | 113.0 (4) | C35—C34—C33 | 115.4 (9) |
C3—C2—N3 | 116.9 (5) | C35—C34—C36 | 109.7 (8) |
C3—C2—C1 | 123.9 (5) | C33—C34—C36 | 112.0 (7) |
N3—C2—C1 | 119.2 (4) | C35—C34—H34 | 106.4 |
C2—C3—C4 | 118.7 (5) | C33—C34—H34 | 106.4 |
C2—C3—H3 | 120.6 | C36—C34—H34 | 106.4 |
C4—C3—H3 | 120.6 | C34—C35—H35A | 109.5 |
C5—C4—C3 | 121.5 (4) | C34—C35—H35B | 109.5 |
C5—C4—N2 | 119.7 (5) | H35A—C35—H35B | 109.5 |
C3—C4—N2 | 118.8 (5) | C34—C35—H35C | 109.5 |
C4—C5—C6 | 119.5 (5) | H35A—C35—H35C | 109.5 |
C4—C5—H5 | 120.3 | H35B—C35—H35C | 109.5 |
C6—C5—H5 | 120.3 | C34—C36—H36A | 109.5 |
C5—C6—N1 | 116.5 (5) | C34—C36—H36B | 109.5 |
C5—C6—C1 | 123.3 (4) | H36A—C36—H36B | 109.5 |
N1—C6—C1 | 120.2 (4) | C34—C36—H36C | 109.5 |
O6—N3—O7 | 121.4 (5) | H36A—C36—H36C | 109.5 |
O6—N3—C2 | 118.7 (5) | H36B—C36—H36C | 109.5 |
O7—N3—C2 | 119.9 (5) | C32—N31—H31A | 109.5 |
O2—N1—O3 | 120.4 (5) | C32—N31—H31B | 109.5 |
O2—N1—C6 | 119.7 (5) | H31A—N31—H31B | 109.5 |
O3—N1—C6 | 119.9 (5) | C32—N31—H31C | 109.5 |
O5—N2—O4 | 123.2 (5) | H31A—N31—H31C | 109.5 |
O5—N2—C4 | 118.6 (5) | H31B—N31—H31C | 109.5 |
O4—N2—C4 | 118.1 (5) | O41A—C41—O41B | 126.4 (5) |
O11—C11—C16 | 124.6 (5) | O41A—C41—C42 | 121.5 (4) |
O11—C11—C12 | 125.1 (5) | O41B—C41—C42 | 112.1 (4) |
C16—C11—C12 | 110.3 (4) | N41—C42—C41 | 109.2 (3) |
C13—C12—N11 | 117.4 (5) | N41—C42—C43 | 111.0 (4) |
C13—C12—C11 | 123.9 (5) | C41—C42—C43 | 110.2 (4) |
N11—C12—C11 | 118.6 (5) | N41—C42—H42 | 108.8 |
C12—C13—C14 | 120.6 (5) | C41—C42—H42 | 108.8 |
C12—C13—H13 | 119.7 | C43—C42—H42 | 108.8 |
C14—C13—H13 | 119.7 | C44—C43—C42 | 115.8 (4) |
C13—C14—C15 | 120.8 (5) | C44—C43—H43A | 108.3 |
C13—C14—N12 | 120.2 (5) | C42—C43—H43A | 108.3 |
C15—C14—N12 | 118.9 (5) | C44—C43—H43B | 108.3 |
C16—C15—C14 | 119.0 (5) | C42—C43—H43B | 108.3 |
C16—C15—H15 | 120.5 | H43A—C43—H43B | 107.4 |
C14—C15—H15 | 120.5 | C44—C45—H45A | 109.5 |
C15—C16—N13 | 116.5 (5) | C44—C45—H45B | 109.5 |
C15—C16—C11 | 125.3 (5) | H45A—C45—H45B | 109.5 |
N13—C16—C11 | 118.2 (4) | C44—C45—H45C | 109.5 |
O13—N11—O12 | 121.8 (6) | H45A—C45—H45C | 109.5 |
O13—N11—C12 | 117.4 (5) | H45B—C45—H45C | 109.5 |
O12—N11—C12 | 120.7 (5) | C45—C44—C46 | 112.2 (5) |
O14—N12—O15 | 122.4 (5) | C45—C44—C43 | 112.3 (5) |
O14—N12—C14 | 118.8 (5) | C46—C44—C43 | 109.6 (5) |
O15—N12—C14 | 118.8 (5) | C45—C44—H44 | 107.5 |
O16—N13—O17 | 122.8 (5) | C46—C44—H44 | 107.5 |
O16—N13—C16 | 119.2 (5) | C43—C44—H44 | 107.5 |
O17—N13—C16 | 118.0 (5) | C44—C46—H46A | 109.5 |
O21A—C21—O21B | 126.4 (4) | C44—C46—H46B | 109.5 |
O21A—C21—C22 | 119.3 (4) | H46A—C46—H46B | 109.5 |
O21B—C21—C22 | 114.2 (4) | C44—C46—H46C | 109.5 |
N21—C22—C21 | 108.7 (4) | H46A—C46—H46C | 109.5 |
N21—C22—C23 | 110.3 (4) | H46B—C46—H46C | 109.5 |
C21—C22—C23 | 112.3 (4) | C42—N41—H41A | 109.5 |
N21—C22—H22 | 108.5 | C42—N41—H41B | 109.5 |
C21—C22—H22 | 108.5 | H41A—N41—H41B | 109.5 |
C23—C22—H22 | 108.5 | C42—N41—H41C | 109.5 |
C24—C23—C22 | 114.6 (5) | H41A—N41—H41C | 109.5 |
C24—C23—H23A | 108.6 | H41B—N41—H41C | 109.5 |
C22—C23—H23A | 108.6 | C41—O41B—H41D | 109.5 |
C24—C23—H23B | 108.6 | O51A—C51—O51B | 125.5 (4) |
C22—C23—H23B | 108.6 | O51A—C51—C52 | 121.8 (4) |
H23A—C23—H23B | 107.6 | O51B—C51—C52 | 112.7 (4) |
C26—C24—C23 | 113.7 (7) | N51—C52—C51 | 108.7 (3) |
C26—C24—C25 | 106.7 (8) | N51—C52—C53 | 110.2 (4) |
C23—C24—C25 | 106.6 (7) | C51—C52—C53 | 112.1 (4) |
C26—C24—H24 | 109.9 | N51—C52—H52 | 108.6 |
C23—C24—H24 | 109.9 | C51—C52—H52 | 108.6 |
C25—C24—H24 | 109.9 | C53—C52—H52 | 108.6 |
C24—C25—H25A | 109.5 | C54—C53—C52 | 115.2 (4) |
C24—C25—H25B | 109.5 | C54—C53—H53A | 108.5 |
H25A—C25—H25B | 109.5 | C52—C53—H53A | 108.5 |
C24—C25—H25C | 109.5 | C54—C53—H53B | 108.5 |
H25A—C25—H25C | 109.5 | C52—C53—H53B | 108.5 |
H25B—C25—H25C | 109.5 | H53A—C53—H53B | 107.5 |
C24—C26—H26A | 109.5 | C53—C54—C55 | 111.4 (5) |
C24—C26—H26B | 109.5 | C53—C54—C56 | 108.8 (5) |
H26A—C26—H26B | 109.5 | C55—C54—C56 | 110.8 (5) |
C24—C26—H26C | 109.5 | C53—C54—H54 | 108.6 |
H26A—C26—H26C | 109.5 | C55—C54—H54 | 108.6 |
H26B—C26—H26C | 109.5 | C56—C54—H54 | 108.6 |
C22—N21—H21A | 109.5 | C54—C55—H55A | 109.5 |
C22—N21—H21B | 109.5 | C54—C55—H55B | 109.5 |
H21A—N21—H21B | 109.5 | H55A—C55—H55B | 109.5 |
C22—N21—H21C | 109.5 | C54—C55—H55C | 109.5 |
H21A—N21—H21C | 109.5 | H55A—C55—H55C | 109.5 |
H21B—N21—H21C | 109.5 | H55B—C55—H55C | 109.5 |
O31A—C31—O31B | 126.4 (4) | C54—C56—H56A | 109.5 |
O31A—C31—C32 | 119.8 (4) | C54—C56—H56B | 109.5 |
O31B—C31—C32 | 113.7 (4) | H56A—C56—H56B | 109.5 |
N31—C32—C33 | 110.3 (4) | C54—C56—H56C | 109.5 |
N31—C32—C31 | 108.6 (4) | H56A—C56—H56C | 109.5 |
C33—C32—C31 | 112.3 (4) | H56B—C56—H56C | 109.5 |
N31—C32—H32 | 108.5 | C52—N51—H51A | 109.5 |
C33—C32—H32 | 108.5 | C52—N51—H51B | 109.5 |
C31—C32—H32 | 108.5 | H51A—N51—H51B | 109.5 |
C34—C33—C32 | 116.2 (5) | C52—N51—H51C | 109.5 |
C34—C33—H33A | 108.2 | H51A—N51—H51C | 109.5 |
C32—C33—H33A | 108.2 | H51B—N51—H51C | 109.5 |
C34—C33—H33B | 108.2 | C51—O51B—H51D | 109.5 |
O1—C1—C2—C3 | −176.1 (5) | C11—C12—N11—O13 | −171.7 (6) |
C6—C1—C2—C3 | 1.5 (7) | C13—C12—N11—O12 | −173.6 (6) |
O1—C1—C2—N3 | 4.6 (7) | C11—C12—N11—O12 | 5.3 (9) |
C6—C1—C2—N3 | −177.8 (5) | C13—C14—N12—O14 | −1.6 (9) |
N3—C2—C3—C4 | 179.6 (5) | C15—C14—N12—O14 | 175.4 (6) |
C1—C2—C3—C4 | 0.3 (8) | C13—C14—N12—O15 | 179.3 (6) |
C2—C3—C4—C5 | −1.3 (8) | C15—C14—N12—O15 | −3.6 (8) |
C2—C3—C4—N2 | 177.7 (5) | C15—C16—N13—O16 | −23.1 (8) |
C3—C4—C5—C6 | 0.3 (8) | C11—C16—N13—O16 | 154.3 (6) |
N2—C4—C5—C6 | −178.6 (5) | C15—C16—N13—O17 | 153.3 (6) |
C4—C5—C6—N1 | −177.1 (5) | C11—C16—N13—O17 | −29.3 (8) |
C4—C5—C6—C1 | 1.7 (7) | O21A—C21—C22—N21 | −9.5 (6) |
O1—C1—C6—C5 | 175.0 (5) | O21B—C21—C22—N21 | 170.4 (4) |
C2—C1—C6—C5 | −2.5 (7) | O21A—C21—C22—C23 | 112.8 (5) |
O1—C1—C6—N1 | −6.2 (7) | O21B—C21—C22—C23 | −67.3 (6) |
C2—C1—C6—N1 | 176.3 (4) | N21—C22—C23—C24 | −78.6 (6) |
C3—C2—N3—O6 | 28.3 (8) | C21—C22—C23—C24 | 160.0 (5) |
C1—C2—N3—O6 | −152.3 (5) | C22—C23—C24—C26 | 163.5 (8) |
C3—C2—N3—O7 | −151.8 (6) | C22—C23—C24—C25 | −79.2 (7) |
C1—C2—N3—O7 | 27.5 (8) | O31A—C31—C32—N31 | −9.5 (6) |
C5—C6—N1—O2 | 166.1 (6) | O31B—C31—C32—N31 | 172.3 (4) |
C1—C6—N1—O2 | −12.8 (8) | O31A—C31—C32—C33 | 112.7 (5) |
C5—C6—N1—O3 | −14.2 (8) | O31B—C31—C32—C33 | −65.5 (6) |
C1—C6—N1—O3 | 166.9 (5) | N31—C32—C33—C34 | −71.0 (8) |
C5—C4—N2—O5 | 177.6 (5) | C31—C32—C33—C34 | 167.8 (7) |
C3—C4—N2—O5 | −1.3 (8) | C32—C33—C34—C35 | −69.7 (11) |
C5—C4—N2—O4 | 2.2 (9) | C32—C33—C34—C36 | 163.9 (8) |
C3—C4—N2—O4 | −176.8 (6) | O41A—C41—C42—N41 | −14.8 (6) |
O11—C11—C12—C13 | −177.3 (5) | O41B—C41—C42—N41 | 168.3 (4) |
C16—C11—C12—C13 | 1.3 (7) | O41A—C41—C42—C43 | 107.4 (5) |
O11—C11—C12—N11 | 4.0 (8) | O41B—C41—C42—C43 | −69.5 (5) |
C16—C11—C12—N11 | −177.5 (5) | N41—C42—C43—C44 | −75.3 (5) |
N11—C12—C13—C14 | 177.1 (5) | C41—C42—C43—C44 | 163.6 (4) |
C11—C12—C13—C14 | −1.7 (8) | C42—C43—C44—C45 | −67.9 (6) |
C12—C13—C14—C15 | 2.5 (8) | C42—C43—C44—C46 | 166.7 (5) |
C12—C13—C14—N12 | 179.5 (5) | O51A—C51—C52—N51 | −11.3 (6) |
C13—C14—C15—C16 | −2.9 (8) | O51B—C51—C52—N51 | 167.2 (4) |
N12—C14—C15—C16 | −179.9 (5) | O51A—C51—C52—C53 | 110.7 (5) |
C14—C15—C16—N13 | 179.9 (5) | O51B—C51—C52—C53 | −70.8 (5) |
C14—C15—C16—C11 | 2.7 (8) | N51—C52—C53—C54 | −76.2 (5) |
O11—C11—C16—C15 | 176.7 (5) | C51—C52—C53—C54 | 162.6 (5) |
C12—C11—C16—C15 | −1.8 (7) | C52—C53—C54—C55 | −74.6 (6) |
O11—C11—C16—N13 | −0.4 (7) | C52—C53—C54—C56 | 162.9 (5) |
C12—C11—C16—N13 | −179.0 (4) | H41D—O21Bi—C21i—O21Ai | 2.5 |
C13—C12—N11—O13 | 9.4 (9) | H51D—O31Bi—C31i—O31Ai | 2.4 |
Symmetry code: (i) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O51B—H51D···O31Bi | 0.82 | 1.65 | 2.454 (5) | 166 |
N51—H51C···O31A | 0.89 | 2.12 | 2.999 (5) | 168 |
N51—H51B···O7 | 0.89 | 2.23 | 3.098 (6) | 164 |
N51—H51A···O21Aii | 0.89 | 1.93 | 2.798 (5) | 166 |
O41B—H41D···O21Bi | 0.82 | 1.68 | 2.471 (5) | 161 |
N41—H41C···O21A | 0.89 | 2.07 | 2.942 (5) | 166 |
N41—H41B···O11iii | 0.89 | 2.02 | 2.907 (5) | 173 |
N41—H41A···O31Aiv | 0.89 | 2.05 | 2.913 (5) | 162 |
N31—H31C···O5v | 0.89 | 2.16 | 2.977 (6) | 153 |
N31—H31B···O17vi | 0.89 | 2.25 | 2.998 (6) | 142 |
N31—H31B···O12 | 0.89 | 2.62 | 3.364 (9) | 142 |
N31—H31A···O51A | 0.89 | 1.97 | 2.861 (5) | 176 |
N21—H21C···O41A | 0.89 | 2.10 | 2.983 (5) | 174 |
N21—H21B···O6iv | 0.89 | 2.57 | 3.355 (6) | 147 |
N21—H21B···O15vii | 0.89 | 2.56 | 3.084 (6) | 118 |
N21—H21A···O1iii | 0.89 | 1.91 | 2.753 (6) | 157 |
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x, y−1, z; (iv) x+1, y−1, z; (v) x, y, z−1; (vi) x−1, y, z; (vii) x, y−1, z+1. |