Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803025224/om6191sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803025224/om6191Isup2.hkl |
CCDC reference: 227883
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELXTL.
C14H20N6O8·2H2O | F(000) = 1840 |
Mr = 436.39 | Dx = 1.541 Mg m−3 |
Monoclinic, C2/c | Melting point = 276–279 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 28.0466 (14) Å | Cell parameters from 7457 reflections |
b = 9.0833 (4) Å | θ = 2.4–30.0° |
c = 14.7948 (7) Å | µ = 0.13 mm−1 |
β = 93.587 (1)° | T = 203 K |
V = 3761.7 (3) Å3 | Block, colorless |
Z = 8 | 0.50 × 0.42 × 0.36 mm |
Bruker SMART CCD area-detector diffractometer | 5486 independent reflections |
Radiation source: fine-focus sealed tube | 4948 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
φ and ω scans | θmax = 30.0°, θmin = 2.4° |
Absorption correction: multi-scan (Blessing, 1995) | h = −38→39 |
Tmin = 0.938, Tmax = 0.954 | k = −12→12 |
36186 measured reflections | l = −20→20 |
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) = 0.099 | All H-atom parameters refined |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0609P)2 + 1.3549P] where P = (Fo2 + 2Fc2)/3 |
5486 reflections | (Δ/σ)max = 0.001 |
380 parameters | Δρmax = 0.37 e Å−3 |
1 restraint | Δρmin = −0.21 e Å−3 |
Experimental. One water molecule was refined as two partial occupancy overlapping moieties (O12, O13). |
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 | Occ. (<1) | |
C1 | 0.37387 (3) | 0.73850 (8) | 0.20556 (5) | 0.02968 (15) | |
H1A | 0.3687 (4) | 0.8381 (12) | 0.2322 (7) | 0.033 (2)* | |
H1B | 0.3961 (4) | 0.6827 (12) | 0.2433 (7) | 0.033 (3)* | |
C1A | 0.36365 (2) | 0.82417 (7) | 0.04842 (4) | 0.01743 (11) | |
C1B | 0.36353 (2) | 0.99363 (7) | 0.05670 (4) | 0.01916 (11) | |
C1C | 0.31877 (3) | 1.22183 (7) | 0.04106 (5) | 0.02681 (14) | |
H1C1 | 0.3482 (4) | 1.2584 (12) | 0.0211 (7) | 0.034 (3)* | |
H1C2 | 0.2935 (4) | 1.2537 (12) | −0.0015 (8) | 0.035 (3)* | |
C1D | 0.31140 (3) | 1.28008 (9) | 0.13520 (6) | 0.03378 (17) | |
H1D1 | 0.3152 (5) | 1.3893 (16) | 0.1313 (8) | 0.051 (3)* | |
H1D2 | 0.3352 (4) | 1.2357 (13) | 0.1802 (8) | 0.039 (3)* | |
N1 | 0.39522 (2) | 0.75929 (6) | 0.11942 (4) | 0.02266 (11) | |
H1 | 0.2954 (4) | 1.0098 (12) | 0.0280 (7) | 0.030 (2)* | |
N1B | 0.32192 (2) | 1.06079 (6) | 0.03901 (4) | 0.02215 (11) | |
O1B | 0.401717 (18) | 1.05661 (6) | 0.07650 (4) | 0.02667 (11) | |
O1D | 0.26446 (2) | 1.24984 (7) | 0.16287 (5) | 0.03978 (14) | |
H1D | 0.2673 (5) | 1.1691 (17) | 0.1967 (9) | 0.061 (4)* | |
C2 | 0.42251 (2) | 0.64749 (7) | 0.08476 (5) | 0.02391 (13) | |
C2A | 0.38407 (2) | 0.76428 (7) | −0.04118 (4) | 0.01754 (11) | |
C2B | 0.40204 (2) | 0.88509 (7) | −0.10424 (4) | 0.01984 (12) | |
C2C | 0.47016 (2) | 1.03136 (8) | −0.14385 (5) | 0.02559 (14) | |
H2C1 | 0.5046 (4) | 1.0167 (12) | −0.1388 (7) | 0.034 (3)* | |
H2C2 | 0.4596 (3) | 1.0240 (11) | −0.2064 (7) | 0.027 (2)* | |
C2D | 0.45767 (3) | 1.18258 (8) | −0.10800 (5) | 0.02645 (14) | |
H2D1 | 0.4236 (4) | 1.1977 (12) | −0.1169 (7) | 0.028 (2)* | |
H2D2 | 0.4739 (4) | 1.2562 (12) | −0.1432 (7) | 0.036 (3)* | |
N2 | 0.421982 (19) | 0.66524 (6) | −0.00784 (4) | 0.02127 (11) | |
H2 | 0.4664 (3) | 0.8642 (11) | −0.0558 (7) | 0.027 (2)* | |
N2B | 0.44844 (2) | 0.91279 (6) | −0.09413 (4) | 0.02098 (11) | |
O2 | 0.44511 (2) | 0.55537 (7) | 0.12906 (4) | 0.03598 (13) | |
O2B | 0.373452 (19) | 0.95101 (6) | −0.15631 (4) | 0.02966 (11) | |
O2D | 0.472674 (18) | 1.20134 (6) | −0.01472 (4) | 0.02756 (11) | |
H2D | 0.4511 (5) | 1.1625 (15) | 0.0157 (9) | 0.051 (3)* | |
C3 | 0.43325 (3) | 0.54469 (8) | −0.06786 (5) | 0.02801 (15) | |
H3A | 0.4541 (4) | 0.4789 (12) | −0.0366 (7) | 0.032 (3)* | |
H3B | 0.4483 (4) | 0.5860 (12) | −0.1208 (7) | 0.028 (2)* | |
O3 | 0.39071 (2) | 0.46702 (6) | −0.09657 (4) | 0.02993 (12) | |
C4 | 0.35748 (3) | 0.56383 (8) | −0.14330 (5) | 0.02778 (14) | |
H4A | 0.3723 (4) | 0.6034 (12) | −0.1944 (7) | 0.033 (3)* | |
H4B | 0.3289 (4) | 0.5091 (12) | −0.1622 (7) | 0.032 (3)* | |
N4 | 0.344093 (19) | 0.68254 (6) | −0.08385 (4) | 0.02019 (11) | |
C5 | 0.30976 (2) | 0.65630 (7) | −0.02198 (4) | 0.01972 (12) | |
N5 | 0.316242 (19) | 0.75896 (6) | 0.04700 (4) | 0.01950 (10) | |
O5 | 0.278291 (18) | 0.56426 (6) | −0.02931 (4) | 0.02762 (11) | |
C6 | 0.29695 (3) | 0.73536 (8) | 0.13479 (5) | 0.02634 (14) | |
H6A | 0.2677 (4) | 0.6758 (12) | 0.1254 (7) | 0.032 (2)* | |
H6B | 0.2905 (4) | 0.8348 (12) | 0.1603 (7) | 0.032 (2)* | |
O6 | 0.33038 (2) | 0.65772 (6) | 0.19346 (3) | 0.03059 (12) | |
O11 | 0.27876 (2) | 1.01451 (7) | 0.28387 (4) | 0.03447 (13) | |
H11A | 0.2680 (5) | 0.9293 (17) | 0.3039 (9) | 0.058 (4)* | |
H11B | 0.3074 (5) | 1.0239 (16) | 0.3112 (9) | 0.052 (3)* | |
O12 | 0.43904 (7) | 0.27734 (18) | 0.21124 (11) | 0.0464 (4) | 0.50 |
H12A | 0.4483 (7) | 0.3599 (19) | 0.1832 (12) | 0.090 (6)* | 0.50 |
H12B | 0.4239 (10) | 0.203 (3) | 0.1746 (19) | 0.060 (8)* | 0.50 |
O13 | 0.45914 (9) | 0.2781 (3) | 0.22596 (18) | 0.0769 (7) | 0.50 |
H13A | 0.4483 (7) | 0.3599 (19) | 0.1832 (12) | 0.090 (6)* | 0.50 |
H13B | 0.4951 (8) | 0.296 (3) | 0.234 (3) | 0.088 (11)* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0427 (4) | 0.0266 (3) | 0.0194 (3) | −0.0040 (3) | −0.0012 (3) | 0.0008 (2) |
C1A | 0.0181 (2) | 0.0149 (2) | 0.0193 (2) | −0.00134 (19) | 0.00075 (19) | 0.00037 (19) |
C1B | 0.0216 (3) | 0.0157 (2) | 0.0204 (2) | −0.0014 (2) | 0.0035 (2) | −0.0008 (2) |
C1C | 0.0280 (3) | 0.0157 (3) | 0.0370 (3) | 0.0016 (2) | 0.0043 (3) | 0.0025 (2) |
C1D | 0.0387 (4) | 0.0206 (3) | 0.0418 (4) | 0.0010 (3) | 0.0008 (3) | −0.0067 (3) |
N1 | 0.0266 (3) | 0.0199 (2) | 0.0208 (2) | 0.0001 (2) | −0.0037 (2) | 0.00176 (19) |
N1B | 0.0213 (2) | 0.0157 (2) | 0.0295 (3) | −0.00040 (19) | 0.0023 (2) | −0.00048 (19) |
O1B | 0.0217 (2) | 0.0209 (2) | 0.0374 (3) | −0.00485 (17) | 0.00208 (19) | −0.00279 (19) |
O1D | 0.0442 (3) | 0.0344 (3) | 0.0420 (3) | 0.0113 (3) | 0.0123 (3) | 0.0017 (2) |
C2 | 0.0224 (3) | 0.0190 (3) | 0.0296 (3) | −0.0012 (2) | −0.0038 (2) | 0.0034 (2) |
C2A | 0.0168 (2) | 0.0153 (2) | 0.0206 (2) | 0.00091 (19) | 0.00126 (19) | 0.00061 (19) |
C2B | 0.0208 (3) | 0.0174 (2) | 0.0216 (3) | 0.0017 (2) | 0.0040 (2) | 0.0012 (2) |
C2C | 0.0244 (3) | 0.0231 (3) | 0.0300 (3) | −0.0014 (2) | 0.0079 (2) | 0.0051 (2) |
C2D | 0.0267 (3) | 0.0206 (3) | 0.0317 (3) | −0.0012 (2) | −0.0006 (3) | 0.0054 (2) |
N2 | 0.0193 (2) | 0.0167 (2) | 0.0278 (3) | 0.00337 (18) | 0.00147 (19) | 0.00249 (19) |
N2B | 0.0198 (2) | 0.0188 (2) | 0.0247 (2) | 0.00124 (19) | 0.00396 (19) | 0.00348 (19) |
O2 | 0.0381 (3) | 0.0282 (3) | 0.0403 (3) | 0.0074 (2) | −0.0084 (2) | 0.0100 (2) |
O2B | 0.0245 (2) | 0.0306 (2) | 0.0336 (3) | 0.0023 (2) | −0.00060 (19) | 0.0124 (2) |
O2D | 0.0233 (2) | 0.0267 (2) | 0.0323 (2) | −0.00401 (19) | −0.00067 (19) | 0.0022 (2) |
C3 | 0.0264 (3) | 0.0201 (3) | 0.0381 (4) | 0.0058 (2) | 0.0064 (3) | −0.0015 (3) |
O3 | 0.0334 (3) | 0.0185 (2) | 0.0380 (3) | 0.00239 (19) | 0.0035 (2) | −0.00552 (19) |
C4 | 0.0327 (3) | 0.0251 (3) | 0.0255 (3) | 0.0016 (3) | 0.0017 (3) | −0.0075 (2) |
N4 | 0.0202 (2) | 0.0189 (2) | 0.0214 (2) | −0.00102 (19) | 0.00079 (18) | −0.00319 (18) |
C5 | 0.0186 (2) | 0.0167 (2) | 0.0236 (3) | 0.0002 (2) | −0.0005 (2) | 0.0001 (2) |
N5 | 0.0197 (2) | 0.0170 (2) | 0.0221 (2) | −0.00359 (18) | 0.00423 (18) | −0.00121 (18) |
O5 | 0.0229 (2) | 0.0229 (2) | 0.0369 (3) | −0.00644 (18) | 0.00028 (19) | −0.00313 (19) |
C6 | 0.0311 (3) | 0.0235 (3) | 0.0255 (3) | −0.0035 (3) | 0.0100 (2) | 0.0012 (2) |
O6 | 0.0423 (3) | 0.0253 (2) | 0.0246 (2) | −0.0051 (2) | 0.0048 (2) | 0.00526 (19) |
O11 | 0.0263 (2) | 0.0308 (3) | 0.0464 (3) | −0.0006 (2) | 0.0028 (2) | 0.0013 (2) |
O12 | 0.0656 (10) | 0.0345 (7) | 0.0386 (7) | −0.0124 (7) | 0.0002 (7) | 0.0005 (5) |
O13 | 0.0775 (15) | 0.0603 (11) | 0.0912 (16) | −0.0139 (11) | −0.0077 (12) | 0.0333 (11) |
C1—O6 | 1.4250 (10) | C2C—H2C1 | 0.973 (11) |
C1—N1 | 1.4540 (9) | C2C—H2C2 | 0.957 (10) |
C1—H1A | 1.001 (11) | C2D—O2D | 1.4277 (9) |
C1—H1B | 0.956 (11) | C2D—H2D1 | 0.965 (10) |
C1A—N5 | 1.4545 (8) | C2D—H2D2 | 0.978 (11) |
C1A—N1 | 1.4555 (8) | N2—C3 | 1.4568 (9) |
C1A—C1B | 1.5441 (8) | N2B—H2 | 0.857 (10) |
C1A—C2A | 1.5736 (8) | O2D—H2D | 0.853 (14) |
C1B—O1B | 1.2332 (8) | C3—O3 | 1.4277 (9) |
C1B—N1B | 1.3285 (8) | C3—H3A | 0.938 (11) |
C1C—N1B | 1.4659 (9) | C3—H3B | 0.988 (10) |
C1C—C1D | 1.5161 (11) | O3—C4 | 1.4281 (9) |
C1C—H1C1 | 0.953 (11) | C4—N4 | 1.4555 (9) |
C1C—H1C2 | 0.964 (11) | C4—H4A | 0.955 (11) |
C1D—O1D | 1.4297 (11) | C4—H4B | 0.969 (11) |
C1D—H1D1 | 0.999 (14) | N4—C5 | 1.3900 (8) |
C1D—H1D2 | 0.998 (11) | C5—O5 | 1.2156 (8) |
N1—C2 | 1.3889 (9) | C5—N5 | 1.3860 (8) |
N1B—H1 | 0.882 (11) | N5—C6 | 1.4539 (9) |
O1D—H1D | 0.888 (15) | C6—O6 | 1.4241 (9) |
C2—O2 | 1.2164 (9) | C6—H6A | 0.985 (11) |
C2—N2 | 1.3787 (9) | C6—H6B | 1.000 (11) |
C2A—N2 | 1.4551 (8) | O11—H11A | 0.888 (15) |
C2A—N4 | 1.4555 (8) | O11—H11B | 0.881 (13) |
C2A—C2B | 1.5452 (9) | O12—H12A | 0.903 (17) |
C2B—O2B | 1.2319 (8) | O12—H12B | 0.95 (3) |
C2B—N2B | 1.3247 (8) | O13—H13A | 1.010 (16) |
C2C—N2B | 1.4588 (9) | O13—H13B | 1.02 (2) |
C2C—C2D | 1.5212 (10) | ||
O6—C1—N1 | 110.67 (6) | N2B—C2C—H2C2 | 108.8 (6) |
O6—C1—H1A | 111.7 (6) | C2D—C2C—H2C2 | 109.7 (6) |
N1—C1—H1A | 107.8 (6) | H2C1—C2C—H2C2 | 108.1 (9) |
O6—C1—H1B | 108.8 (7) | O2D—C2D—C2C | 112.61 (6) |
N1—C1—H1B | 107.0 (6) | O2D—C2D—H2D1 | 110.2 (6) |
H1A—C1—H1B | 110.8 (9) | C2C—C2D—H2D1 | 109.1 (6) |
N5—C1A—N1 | 111.09 (5) | O2D—C2D—H2D2 | 108.3 (6) |
N5—C1A—C1B | 113.62 (5) | C2C—C2D—H2D2 | 107.8 (7) |
N1—C1A—C1B | 110.52 (5) | H2D1—C2D—H2D2 | 108.7 (9) |
N5—C1A—C2A | 103.16 (5) | C2—N2—C2A | 111.80 (5) |
N1—C1A—C2A | 103.35 (5) | C2—N2—C3 | 121.90 (6) |
C1B—C1A—C2A | 114.47 (5) | C2A—N2—C3 | 116.10 (5) |
O1B—C1B—N1B | 124.96 (6) | C2B—N2B—C2C | 121.43 (6) |
O1B—C1B—C1A | 118.37 (6) | C2B—N2B—H2 | 120.6 (7) |
N1B—C1B—C1A | 116.64 (5) | C2C—N2B—H2 | 117.9 (7) |
N1B—C1C—C1D | 112.28 (6) | C2D—O2D—H2D | 106.6 (8) |
N1B—C1C—H1C1 | 106.7 (7) | O3—C3—N2 | 110.10 (6) |
C1D—C1C—H1C1 | 109.5 (7) | O3—C3—H3A | 108.4 (7) |
N1B—C1C—H1C2 | 109.2 (7) | N2—C3—H3A | 109.4 (7) |
C1D—C1C—H1C2 | 111.0 (7) | O3—C3—H3B | 110.1 (6) |
H1C1—C1C—H1C2 | 108.0 (9) | N2—C3—H3B | 108.5 (6) |
O1D—C1D—C1C | 112.14 (7) | H3A—C3—H3B | 110.3 (9) |
O1D—C1D—H1D1 | 108.1 (7) | C3—O3—C4 | 110.35 (6) |
C1C—C1D—H1D1 | 105.8 (7) | O3—C4—N4 | 110.41 (6) |
O1D—C1D—H1D2 | 108.8 (7) | O3—C4—H4A | 108.2 (6) |
C1C—C1D—H1D2 | 110.3 (7) | N4—C4—H4A | 109.9 (7) |
H1D1—C1D—H1D2 | 111.7 (10) | O3—C4—H4B | 109.1 (6) |
C2—N1—C1 | 119.69 (6) | N4—C4—H4B | 108.3 (6) |
C2—N1—C1A | 110.74 (5) | H4A—C4—H4B | 111.0 (9) |
C1—N1—C1A | 114.82 (6) | C5—N4—C4 | 119.10 (6) |
C1B—N1B—C1C | 120.49 (6) | C5—N4—C2A | 110.39 (5) |
C1B—N1B—H1 | 121.0 (7) | C4—N4—C2A | 114.79 (5) |
C1C—N1B—H1 | 118.5 (7) | O5—C5—N5 | 126.12 (6) |
C1D—O1D—H1D | 105.6 (9) | O5—C5—N4 | 126.03 (6) |
O2—C2—N2 | 126.07 (7) | N5—C5—N4 | 107.77 (5) |
O2—C2—N1 | 125.78 (7) | C5—N5—C6 | 121.31 (5) |
N2—C2—N1 | 108.02 (5) | C5—N5—C1A | 111.24 (5) |
N2—C2A—N4 | 111.00 (5) | C6—N5—C1A | 115.99 (5) |
N2—C2A—C2B | 112.62 (5) | O6—C6—N5 | 110.47 (6) |
N4—C2A—C2B | 111.83 (5) | O6—C6—H6A | 109.0 (6) |
N2—C2A—C1A | 103.01 (5) | N5—C6—H6A | 107.9 (6) |
N4—C2A—C1A | 103.33 (5) | O6—C6—H6B | 110.2 (6) |
C2B—C2A—C1A | 114.38 (5) | N5—C6—H6B | 106.9 (6) |
O2B—C2B—N2B | 125.08 (6) | H6A—C6—H6B | 112.3 (9) |
O2B—C2B—C2A | 119.91 (6) | C6—O6—C1 | 110.32 (5) |
N2B—C2B—C2A | 114.96 (5) | H11A—O11—H11B | 104.5 (13) |
N2B—C2C—C2D | 112.23 (6) | H12A—O12—H12B | 117 (2) |
N2B—C2C—H2C1 | 107.7 (7) | H13A—O13—H13B | 102 (2) |
C2D—C2C—H2C1 | 110.2 (7) | ||
N5—C1A—C1B—O1B | 165.77 (6) | N1—C2—N2—C3 | −159.59 (6) |
N1—C1A—C1B—O1B | 40.11 (8) | N4—C2A—N2—C2 | −103.23 (6) |
C2A—C1A—C1B—O1B | −76.07 (7) | C2B—C2A—N2—C2 | 130.50 (6) |
N5—C1A—C1B—N1B | −16.19 (8) | C1A—C2A—N2—C2 | 6.77 (7) |
N1—C1A—C1B—N1B | −141.85 (6) | N4—C2A—N2—C3 | 42.84 (7) |
C2A—C1A—C1B—N1B | 101.98 (6) | C2B—C2A—N2—C3 | −83.43 (7) |
N1B—C1C—C1D—O1D | −71.57 (8) | C1A—C2A—N2—C3 | 152.84 (5) |
O6—C1—N1—C2 | −82.18 (8) | O2B—C2B—N2B—C2C | 1.93 (10) |
O6—C1—N1—C1A | 53.29 (8) | C2A—C2B—N2B—C2C | −175.32 (6) |
N5—C1A—N1—C2 | 96.18 (6) | C2D—C2C—N2B—C2B | 72.89 (8) |
C1B—C1A—N1—C2 | −136.75 (6) | C2—N2—C3—O3 | 90.95 (7) |
C2A—C1A—N1—C2 | −13.84 (7) | C2A—N2—C3—O3 | −51.43 (8) |
N5—C1A—N1—C1 | −43.17 (7) | N2—C3—O3—C4 | 59.48 (8) |
C1B—C1A—N1—C1 | 83.90 (7) | C3—O3—C4—N4 | −61.09 (8) |
C2A—C1A—N1—C1 | −153.19 (5) | O3—C4—N4—C5 | −80.44 (8) |
O1B—C1B—N1B—C1C | 0.71 (10) | O3—C4—N4—C2A | 53.69 (8) |
C1A—C1B—N1B—C1C | −177.19 (6) | N2—C2A—N4—C5 | 94.43 (6) |
C1D—C1C—N1B—C1B | −86.80 (8) | C2B—C2A—N4—C5 | −138.87 (5) |
C1—N1—C2—O2 | −28.05 (10) | C1A—C2A—N4—C5 | −15.37 (6) |
C1A—N1—C2—O2 | −165.16 (7) | N2—C2A—N4—C4 | −43.58 (7) |
C1—N1—C2—N2 | 155.81 (6) | C2B—C2A—N4—C4 | 83.12 (7) |
C1A—N1—C2—N2 | 18.70 (7) | C1A—C2A—N4—C4 | −153.38 (5) |
N5—C1A—C2A—N2 | −111.63 (5) | C4—N4—C5—O5 | −25.79 (10) |
N1—C1A—C2A—N2 | 4.17 (6) | C2A—N4—C5—O5 | −161.75 (6) |
C1B—C1A—C2A—N2 | 124.42 (5) | C4—N4—C5—N5 | 157.38 (6) |
N5—C1A—C2A—N4 | 4.01 (6) | C2A—N4—C5—N5 | 21.43 (7) |
N1—C1A—C2A—N4 | 119.81 (5) | O5—C5—N5—C6 | 22.69 (10) |
C1B—C1A—C2A—N4 | −119.94 (5) | N4—C5—N5—C6 | −160.49 (6) |
N5—C1A—C2A—C2B | 125.81 (5) | O5—C5—N5—C1A | 164.56 (6) |
N1—C1A—C2A—C2B | −118.39 (5) | N4—C5—N5—C1A | −18.61 (7) |
C1B—C1A—C2A—C2B | 1.86 (7) | N1—C1A—N5—C5 | −101.57 (6) |
N2—C2A—C2B—O2B | 160.42 (6) | C1B—C1A—N5—C5 | 133.06 (5) |
N4—C2A—C2B—O2B | 34.60 (8) | C2A—C1A—N5—C5 | 8.56 (6) |
C1A—C2A—C2B—O2B | −82.42 (7) | N1—C1A—N5—C6 | 42.49 (7) |
N2—C2A—C2B—N2B | −22.18 (8) | C1B—C1A—N5—C6 | −82.87 (7) |
N4—C2A—C2B—N2B | −147.99 (6) | C2A—C1A—N5—C6 | 152.63 (5) |
C1A—C2A—C2B—N2B | 94.99 (6) | C5—N5—C6—O6 | 88.92 (7) |
N2B—C2C—C2D—O2D | 59.19 (8) | C1A—N5—C6—O6 | −51.27 (7) |
O2—C2—N2—C2A | 168.10 (7) | N5—C6—O6—C1 | 59.29 (7) |
N1—C2—N2—C2A | −15.78 (7) | N1—C1—O6—C6 | −60.69 (8) |
O2—C2—N2—C3 | 24.29 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11B···O2Bi | 0.881 (13) | 1.898 (14) | 2.7642 (8) | 167.4 (13) |
O11—H11A···O1Dii | 0.888 (15) | 1.945 (15) | 2.8264 (9) | 171.3 (13) |
N2B—H2···O2Diii | 0.857 (10) | 2.035 (10) | 2.8491 (8) | 158.4 (9) |
O2D—H2D···O1B | 0.853 (14) | 1.951 (14) | 2.8011 (8) | 174.1 (13) |
O1D—H1D···O11 | 0.888 (15) | 1.921 (15) | 2.8009 (9) | 170.8 (14) |
N1B—H1···O5iv | 0.882 (11) | 2.176 (11) | 3.0264 (8) | 162.0 (10) |
O12—H12A···O2 | 0.903 (17) | 1.948 (17) | 2.8127 (18) | 159.8 (17) |
O12—H12B···O1Bv | 0.95 (3) | 2.04 (3) | 2.9712 (17) | 168 (3) |
O13—H13A···O2 | 1.01 (2) | 1.95 (2) | 2.912 (2) | 159 (2) |
Symmetry codes: (i) x, −y+2, z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+1, −y+2, −z; (iv) −x+1/2, −y+3/2, −z; (v) x, y−1, z. |