Due to the inherent geometrical interdependencies of nucleic acid structures, the ability to engineer biosensors that rely on the specific interactions of these compounds is of considerable importance. Additionally, sensing or screening in a label-free fashion is a capability of these structures that can be readily achieved by exploiting the fluorescent component. In this work, the [AdH]6[V10O28].4(H2O) (1) supramolecular structure is introduced using adenine and decavanadate moieties that allow probing of selectivity to specific nucleic acid binding events by optical changes. The structure of (1) is an alternating organic–inorganic hybrid architecture of cationic adeninium (AdH+) ribbons and anionic decavanadate (DV)–water sheets. The luminescent screening and anticancer activity of compound (1) on the two human mammary carcinoma cell lines MDA-MB-231 and MCF7 were investigated using fluorescent microscopy and MTT assays, respectively. It was found that compound (1) is cell permeable with no toxicity below 12.5 µM concentration and moderate cytotoxicity at concentrations as high as 200 µM in human breast cancer cell lines, making it a useful tool to study the cell nucleus in real time.
Supporting information
CCDC reference: 1910672
Data collection: CrysAlis CCD 1.171.38.41 (Rigaku Oxford Diffraction, 2015; cell refinement: CrysAlis RED 1.171.38.41 (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis RED 1.171.38.41 (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2014); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2018); molecular graphics: Brandenburg & Putz (2006). Diamond 3.0. Crystal and Molecular
Structure Visualisation, University of Bonn, Germany; software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2018).
Crystal data top
O28V10·6(C5H6N5)·4(H2O) | Z = 1 |
Mr = 1846.35 | F(000) = 920 |
Triclinic, P1 | Dx = 2.070 Mg m−3 |
a = 11.3756 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.5611 (3) Å | Cell parameters from 15803 reflections |
c = 14.0894 (4) Å | θ = 3.0–29.3° |
α = 73.533 (2)° | µ = 1.62 mm−1 |
β = 67.176 (3)° | T = 100 K |
γ = 60.845 (3)° | Parallelepiped, yellow |
V = 1481.18 (9) Å3 | 0.14 × 0.12 × 0.07 mm |
Data collection top
KUMA KM-4 with CCD detector diffractometer | 7654 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 5898 reflections with I > 2σ(I) |
Detector resolution: 10.6249 pixels mm-1 | Rint = 0.039 |
ω–scan | θmax = 29.5°, θmin = 2.4° |
Absorption correction: multi-scan CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | h = −15→15 |
Tmin = 0.897, Tmax = 1.000 | k = −15→15 |
48373 measured reflections | l = −19→19 |
Refinement top
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: mixed |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0457P)2 + 1.4419P] where P = (Fo2 + 2Fc2)/3 |
7654 reflections | (Δ/σ)max = 0.001 |
460 parameters | Δρmax = 1.42 e Å−3 |
0 restraints | Δρmin = −0.53 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
V1 | 1.01943 (4) | 0.47426 (4) | 0.38479 (3) | 0.01774 (10) | |
V2 | 0.75387 (4) | 0.47450 (4) | 0.57856 (3) | 0.01838 (10) | |
V3 | 0.69263 (5) | 0.75569 (4) | 0.60968 (3) | 0.02034 (10) | |
V4 | 0.95368 (5) | 0.75566 (4) | 0.42078 (3) | 0.01902 (10) | |
V5 | 0.72245 (5) | 0.70485 (4) | 0.39759 (3) | 0.02039 (10) | |
O1 | 0.93212 (18) | 0.35794 (15) | 0.47808 (12) | 0.0193 (3) | |
O2 | 1.16007 (18) | 0.35347 (16) | 0.31411 (12) | 0.0202 (3) | |
O3 | 1.09951 (18) | 0.59900 (15) | 0.34858 (12) | 0.0192 (3) | |
O4 | 0.87397 (18) | 0.59893 (15) | 0.50036 (12) | 0.0193 (3) | |
O5 | 0.68471 (19) | 0.36891 (16) | 0.63157 (13) | 0.0228 (4) | |
O6 | 0.64651 (18) | 0.60822 (16) | 0.65738 (12) | 0.0208 (3) | |
O7 | 0.57573 (19) | 0.85740 (17) | 0.69275 (13) | 0.0245 (4) | |
O8 | 0.80903 (18) | 0.84110 (15) | 0.53320 (12) | 0.0204 (3) | |
O9 | 1.02660 (19) | 0.85762 (16) | 0.36718 (12) | 0.0218 (4) | |
O10 | 0.90196 (18) | 0.55684 (15) | 0.31664 (12) | 0.0203 (3) | |
O11 | 0.67744 (18) | 0.56156 (16) | 0.47033 (12) | 0.0213 (4) | |
O12 | 0.61171 (18) | 0.80470 (16) | 0.50419 (13) | 0.0219 (4) | |
O13 | 0.83868 (19) | 0.79814 (16) | 0.34624 (12) | 0.0215 (4) | |
O14 | 0.63272 (19) | 0.76768 (16) | 0.31643 (13) | 0.0247 (4) | |
C1 | 0.3475 (2) | 0.5426 (2) | 0.94107 (18) | 0.0165 (4) | |
N2 | 0.33193 (19) | 0.56925 (18) | 1.03605 (15) | 0.0175 (4) | |
C3 | 0.3258 (2) | 0.4621 (2) | 1.09959 (19) | 0.0194 (5) | |
H3 | 0.315929 | 0.450896 | 1.171319 | 0.023* | |
N4 | 0.3353 (2) | 0.36916 (19) | 1.05160 (16) | 0.0213 (4) | |
H4 | 0.332565 | 0.292005 | 1.080717 | 0.026* | |
C5 | 0.3496 (2) | 0.4191 (2) | 0.95025 (19) | 0.0195 (5) | |
N6 | 0.3611 (2) | 0.36092 (19) | 0.87352 (17) | 0.0224 (4) | |
C7 | 0.3726 (3) | 0.4351 (2) | 0.7835 (2) | 0.0237 (5) | |
H7 | 0.382949 | 0.400795 | 0.725548 | 0.028* | |
N8 | 0.3708 (2) | 0.5584 (2) | 0.76725 (16) | 0.0213 (4) | |
H8 | 0.378387 | 0.600830 | 0.704078 | 0.026* | |
C9 | 0.3581 (2) | 0.6196 (2) | 0.84274 (18) | 0.0170 (4) | |
N10 | 0.3541 (2) | 0.73872 (19) | 0.82210 (15) | 0.0190 (4) | |
H10A | 0.359676 | 0.780541 | 0.758815 | 0.023* | |
H10B | 0.345918 | 0.777166 | 0.871463 | 0.023* | |
C11 | 0.3241 (2) | 0.9367 (2) | 1.03888 (18) | 0.0175 (5) | |
N12 | 0.3366 (2) | 0.91061 (18) | 0.94480 (15) | 0.0178 (4) | |
C13 | 0.3480 (2) | 1.0144 (2) | 0.8799 (2) | 0.0212 (5) | |
H13 | 0.358090 | 1.024472 | 0.808269 | 0.025* | |
N14 | 0.3438 (2) | 1.10636 (18) | 0.92609 (16) | 0.0212 (4) | |
H14 | 0.349920 | 1.181872 | 0.895763 | 0.025* | |
C15 | 0.3283 (2) | 1.0583 (2) | 1.0277 (2) | 0.0200 (5) | |
N16 | 0.3180 (2) | 1.1157 (2) | 1.10425 (18) | 0.0246 (5) | |
C17 | 0.3007 (3) | 1.0437 (2) | 1.1949 (2) | 0.0249 (5) | |
H17 | 0.292555 | 1.077961 | 1.252068 | 0.030* | |
N18 | 0.2932 (2) | 0.92530 (19) | 1.21491 (16) | 0.0217 (4) | |
H18 | 0.281301 | 0.885380 | 1.278902 | 0.026* | |
C19 | 0.3036 (2) | 0.8657 (2) | 1.13908 (18) | 0.0184 (5) | |
N20 | 0.2930 (2) | 0.75192 (18) | 1.16150 (16) | 0.0210 (4) | |
H20A | 0.279074 | 0.713379 | 1.225867 | 0.025* | |
H20B | 0.299824 | 0.714435 | 1.112104 | 0.025* | |
C21 | 0.9884 (2) | 0.1981 (2) | 0.04875 (17) | 0.0154 (4) | |
N22 | 0.9991 (2) | 0.17174 (18) | −0.04524 (14) | 0.0164 (4) | |
C23 | 1.0092 (2) | 0.2759 (2) | −0.11035 (19) | 0.0188 (5) | |
H23 | 1.017509 | 0.286225 | −0.181687 | 0.023* | |
N24 | 1.0065 (2) | 0.36801 (18) | −0.06514 (16) | 0.0199 (4) | |
H24 | 1.012613 | 0.443451 | −0.095842 | 0.024* | |
C25 | 0.9926 (2) | 0.3197 (2) | 0.03639 (19) | 0.0180 (5) | |
N26 | 0.9839 (2) | 0.37757 (19) | 0.11230 (17) | 0.0220 (4) | |
C27 | 0.9709 (3) | 0.3035 (2) | 0.2022 (2) | 0.0240 (5) | |
H27 | 0.964169 | 0.337723 | 0.258914 | 0.029* | |
N28 | 0.9662 (2) | 0.18378 (19) | 0.22311 (15) | 0.0194 (4) | |
H28 | 0.957257 | 0.142999 | 0.286824 | 0.023* | |
C29 | 0.9750 (2) | 0.1248 (2) | 0.14763 (18) | 0.0165 (4) | |
N30 | 0.9707 (2) | 0.00817 (18) | 0.16995 (15) | 0.0185 (4) | |
H30A | 0.962105 | −0.032284 | 0.233749 | 0.022* | |
H30B | 0.976380 | −0.029384 | 0.121066 | 0.022* | |
O1W | 0.3885 (2) | 0.6393 (2) | 0.56410 (16) | 0.0380 (5) | |
H1WA | 0.339507 | 0.668319 | 0.524831 | 0.057* | |
H1WB | 0.473777 | 0.617405 | 0.527186 | 0.057* | |
O2W | 0.32070 (19) | 0.91226 (18) | 0.63433 (14) | 0.0306 (4) | |
H2WA | 0.396295 | 0.896485 | 0.585078 | 0.046* | |
H2WB | 0.290252 | 0.993573 | 0.640940 | 0.046* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
V1 | 0.0329 (2) | 0.01253 (18) | 0.01039 (19) | −0.01026 (17) | −0.00896 (16) | −0.00043 (14) |
V2 | 0.0290 (2) | 0.01462 (19) | 0.0137 (2) | −0.01139 (17) | −0.00732 (16) | 0.00048 (14) |
V3 | 0.0293 (2) | 0.0176 (2) | 0.0147 (2) | −0.00965 (17) | −0.00489 (17) | −0.00560 (15) |
V4 | 0.0333 (2) | 0.01293 (19) | 0.01222 (19) | −0.01138 (17) | −0.00618 (17) | −0.00138 (14) |
V5 | 0.0338 (2) | 0.01505 (19) | 0.0138 (2) | −0.01072 (17) | −0.00912 (17) | −0.00039 (14) |
O1 | 0.0317 (9) | 0.0175 (8) | 0.0118 (8) | −0.0126 (7) | −0.0080 (7) | −0.0002 (6) |
O2 | 0.0340 (10) | 0.0181 (8) | 0.0122 (8) | −0.0140 (7) | −0.0066 (7) | −0.0018 (6) |
O3 | 0.0335 (9) | 0.0151 (8) | 0.0129 (8) | −0.0124 (7) | −0.0094 (7) | 0.0003 (6) |
O4 | 0.0315 (9) | 0.0173 (8) | 0.0125 (8) | −0.0122 (7) | −0.0081 (7) | −0.0009 (6) |
O5 | 0.0355 (10) | 0.0192 (8) | 0.0187 (9) | −0.0152 (8) | −0.0095 (7) | −0.0004 (7) |
O6 | 0.0294 (9) | 0.0185 (8) | 0.0147 (8) | −0.0114 (7) | −0.0046 (7) | −0.0030 (6) |
O7 | 0.0319 (10) | 0.0226 (9) | 0.0200 (9) | −0.0115 (8) | −0.0048 (7) | −0.0085 (7) |
O8 | 0.0327 (9) | 0.0151 (8) | 0.0143 (8) | −0.0108 (7) | −0.0063 (7) | −0.0029 (6) |
O9 | 0.0372 (10) | 0.0159 (8) | 0.0150 (8) | −0.0134 (7) | −0.0087 (7) | −0.0004 (6) |
O10 | 0.0356 (10) | 0.0172 (8) | 0.0135 (8) | −0.0141 (7) | −0.0099 (7) | −0.0004 (6) |
O11 | 0.0335 (10) | 0.0166 (8) | 0.0159 (8) | −0.0113 (7) | −0.0095 (7) | −0.0006 (6) |
O12 | 0.0314 (9) | 0.0157 (8) | 0.0184 (8) | −0.0081 (7) | −0.0090 (7) | −0.0031 (6) |
O13 | 0.0363 (10) | 0.0169 (8) | 0.0145 (8) | −0.0131 (7) | −0.0084 (7) | −0.0017 (6) |
O14 | 0.0399 (11) | 0.0175 (8) | 0.0198 (9) | −0.0121 (8) | −0.0135 (8) | −0.0001 (7) |
C1 | 0.0114 (10) | 0.0139 (10) | 0.0230 (12) | −0.0052 (8) | −0.0046 (9) | −0.0016 (9) |
N2 | 0.0145 (9) | 0.0161 (9) | 0.0180 (10) | −0.0072 (8) | −0.0010 (8) | −0.0008 (7) |
C3 | 0.0148 (11) | 0.0157 (11) | 0.0229 (12) | −0.0059 (9) | −0.0038 (9) | 0.0007 (9) |
N4 | 0.0206 (10) | 0.0139 (9) | 0.0284 (11) | −0.0090 (8) | −0.0075 (9) | 0.0024 (8) |
C5 | 0.0118 (10) | 0.0138 (10) | 0.0299 (13) | −0.0042 (9) | −0.0039 (9) | −0.0040 (9) |
N6 | 0.0198 (10) | 0.0174 (10) | 0.0308 (12) | −0.0084 (8) | −0.0055 (9) | −0.0059 (8) |
C7 | 0.0216 (12) | 0.0205 (12) | 0.0324 (14) | −0.0112 (10) | −0.0057 (10) | −0.0070 (10) |
N8 | 0.0239 (11) | 0.0228 (10) | 0.0214 (10) | −0.0149 (9) | −0.0027 (8) | −0.0050 (8) |
C9 | 0.0123 (10) | 0.0190 (11) | 0.0203 (12) | −0.0084 (9) | −0.0025 (9) | −0.0034 (9) |
N10 | 0.0233 (10) | 0.0193 (10) | 0.0159 (10) | −0.0130 (8) | −0.0033 (8) | −0.0004 (7) |
C11 | 0.0129 (10) | 0.0143 (10) | 0.0241 (12) | −0.0047 (9) | −0.0045 (9) | −0.0043 (9) |
N12 | 0.0157 (9) | 0.0146 (9) | 0.0213 (10) | −0.0070 (8) | −0.0034 (8) | −0.0013 (7) |
C13 | 0.0180 (11) | 0.0147 (11) | 0.0255 (13) | −0.0063 (9) | −0.0031 (10) | −0.0012 (9) |
N14 | 0.0149 (9) | 0.0115 (9) | 0.0318 (12) | −0.0059 (8) | −0.0022 (8) | −0.0014 (8) |
C15 | 0.0115 (10) | 0.0131 (10) | 0.0332 (14) | −0.0028 (9) | −0.0064 (10) | −0.0042 (9) |
N16 | 0.0177 (10) | 0.0175 (10) | 0.0400 (13) | −0.0063 (8) | −0.0091 (9) | −0.0069 (9) |
C17 | 0.0214 (12) | 0.0193 (12) | 0.0377 (15) | −0.0065 (10) | −0.0118 (11) | −0.0084 (11) |
N18 | 0.0261 (11) | 0.0182 (10) | 0.0217 (10) | −0.0081 (8) | −0.0104 (9) | −0.0014 (8) |
C19 | 0.0165 (11) | 0.0153 (11) | 0.0224 (12) | −0.0047 (9) | −0.0063 (9) | −0.0040 (9) |
N20 | 0.0282 (11) | 0.0137 (9) | 0.0197 (10) | −0.0080 (8) | −0.0092 (9) | 0.0011 (8) |
C21 | 0.0129 (10) | 0.0140 (10) | 0.0179 (11) | −0.0053 (8) | −0.0017 (8) | −0.0049 (8) |
N22 | 0.0170 (9) | 0.0136 (9) | 0.0163 (9) | −0.0072 (8) | −0.0012 (8) | −0.0027 (7) |
C23 | 0.0171 (11) | 0.0129 (10) | 0.0222 (12) | −0.0066 (9) | −0.0011 (9) | −0.0024 (9) |
N24 | 0.0179 (10) | 0.0108 (9) | 0.0292 (11) | −0.0077 (8) | −0.0047 (8) | −0.0001 (8) |
C25 | 0.0120 (10) | 0.0135 (10) | 0.0273 (13) | −0.0035 (9) | −0.0040 (9) | −0.0069 (9) |
N26 | 0.0181 (10) | 0.0147 (9) | 0.0348 (12) | −0.0059 (8) | −0.0081 (9) | −0.0070 (8) |
C27 | 0.0278 (13) | 0.0187 (12) | 0.0288 (13) | −0.0096 (10) | −0.0092 (11) | −0.0069 (10) |
N28 | 0.0269 (11) | 0.0177 (9) | 0.0159 (10) | −0.0097 (8) | −0.0068 (8) | −0.0042 (7) |
C29 | 0.0154 (11) | 0.0164 (11) | 0.0190 (11) | −0.0050 (9) | −0.0060 (9) | −0.0059 (9) |
N30 | 0.0246 (10) | 0.0169 (9) | 0.0150 (9) | −0.0109 (8) | −0.0039 (8) | −0.0022 (7) |
O1W | 0.0386 (12) | 0.0442 (12) | 0.0334 (11) | −0.0154 (10) | −0.0142 (9) | −0.0068 (9) |
O2W | 0.0304 (10) | 0.0229 (9) | 0.0295 (10) | −0.0049 (8) | −0.0093 (8) | −0.0022 (8) |
Geometric parameters (Å, º) top
V1—O10 | 1.6887 (17) | N6—C7 | 1.313 (3) |
V1—O2 | 1.6962 (17) | C7—N8 | 1.369 (3) |
V1—O3 | 1.9163 (16) | C7—H7 | 0.9500 |
V1—O1 | 1.9517 (16) | N8—C9 | 1.364 (3) |
V1—O4 | 2.0936 (16) | N8—H8 | 0.8800 |
V1—O4i | 2.1334 (16) | C9—N10 | 1.306 (3) |
V1—V3i | 3.0657 (6) | N10—H10A | 0.8800 |
V1—V5 | 3.0947 (6) | N10—H10B | 0.8800 |
V1—V4 | 3.1098 (5) | C11—N12 | 1.381 (3) |
V2—O5 | 1.6217 (17) | C11—C15 | 1.392 (3) |
V2—O6 | 1.7878 (16) | C11—C19 | 1.412 (3) |
V2—O11 | 1.8440 (16) | N12—C13 | 1.315 (3) |
V2—O3i | 2.0025 (17) | C13—N14 | 1.369 (3) |
V2—O1 | 2.0307 (17) | C13—H13 | 0.9500 |
V2—O4 | 2.2357 (16) | N14—C15 | 1.356 (3) |
V2—V4i | 3.0875 (6) | N14—H14 | 0.8800 |
V2—V3 | 3.1000 (5) | C15—N16 | 1.360 (3) |
V2—V5 | 3.1066 (5) | N16—C17 | 1.313 (3) |
V3—O7 | 1.6031 (17) | C17—N18 | 1.355 (3) |
V3—O12 | 1.8581 (17) | C17—H17 | 0.9500 |
V3—O8 | 1.8583 (17) | N18—C19 | 1.368 (3) |
V3—O6 | 1.8926 (17) | N18—H18 | 0.8800 |
V3—O2i | 2.0300 (17) | C19—N20 | 1.317 (3) |
V3—O4 | 2.3211 (16) | N20—H20A | 0.8800 |
V3—V5 | 3.0668 (6) | N20—H20B | 0.8800 |
V4—O9 | 1.6155 (17) | C21—C25 | 1.389 (3) |
V4—O13 | 1.7897 (17) | C21—N22 | 1.389 (3) |
V4—O8 | 1.8637 (16) | C21—C29 | 1.405 (3) |
V4—O3 | 1.9685 (16) | N22—C23 | 1.316 (3) |
V4—O1i | 2.0385 (16) | C23—N24 | 1.371 (3) |
V4—O4 | 2.2412 (16) | C23—H23 | 0.9500 |
V4—V5 | 3.1068 (6) | N24—C25 | 1.357 (3) |
V5—O14 | 1.6091 (17) | N24—H24 | 0.8800 |
V5—O12 | 1.8094 (16) | C25—N26 | 1.364 (3) |
V5—O11 | 1.8744 (16) | N26—C27 | 1.312 (3) |
V5—O13 | 1.9079 (17) | C27—N28 | 1.355 (3) |
V5—O10 | 2.0721 (17) | C27—H27 | 0.9500 |
V5—O4 | 2.3327 (16) | N28—C29 | 1.367 (3) |
C1—N2 | 1.383 (3) | N28—H28 | 0.8800 |
C1—C5 | 1.386 (3) | C29—N30 | 1.316 (3) |
C1—C9 | 1.415 (3) | N30—H30A | 0.8800 |
N2—C3 | 1.322 (3) | N30—H30B | 0.8800 |
C3—N4 | 1.366 (3) | O1W—H1WA | 0.8256 |
C3—H3 | 0.9500 | O1W—H1WB | 0.8479 |
N4—C5 | 1.357 (3) | O2W—H2WA | 0.8427 |
N4—H4 | 0.8800 | O2W—H2WB | 0.8484 |
C5—N6 | 1.362 (3) | | |
| | | |
O10—V1—O2 | 106.86 (8) | O11—V5—O13 | 154.17 (8) |
O10—V1—O3 | 98.37 (7) | O14—V5—O10 | 100.09 (8) |
O2—V1—O3 | 97.39 (8) | O12—V5—O10 | 155.69 (7) |
O10—V1—O1 | 96.88 (8) | O11—V5—O10 | 82.96 (7) |
O2—V1—O1 | 95.79 (7) | O13—V5—O10 | 82.81 (7) |
O3—V1—O1 | 155.99 (7) | O14—V5—O4 | 173.37 (8) |
O10—V1—O4 | 87.79 (7) | O12—V5—O4 | 82.37 (7) |
O2—V1—O4 | 165.26 (7) | O11—V5—O4 | 78.04 (6) |
O3—V1—O4 | 81.72 (7) | O13—V5—O4 | 77.27 (6) |
O1—V1—O4 | 80.46 (6) | O10—V5—O4 | 73.33 (6) |
O10—V1—O4i | 165.59 (7) | O14—V5—V3 | 137.94 (6) |
O2—V1—O4i | 87.47 (7) | O12—V5—V3 | 33.76 (5) |
O3—V1—O4i | 80.84 (6) | O11—V5—V3 | 85.72 (5) |
O1—V1—O4i | 79.79 (6) | O13—V5—V3 | 83.67 (5) |
O4—V1—O4i | 77.85 (7) | O10—V5—V3 | 121.94 (5) |
O10—V1—V3i | 145.21 (6) | O4—V5—V3 | 48.61 (4) |
O2—V1—V3i | 38.36 (6) | O14—V5—V1 | 130.86 (6) |
O3—V1—V3i | 89.73 (5) | O12—V5—V1 | 124.92 (6) |
O1—V1—V3i | 88.23 (5) | O11—V5—V1 | 78.77 (5) |
O4—V1—V3i | 126.95 (5) | O13—V5—V1 | 77.97 (5) |
O4i—V1—V3i | 49.11 (4) | O10—V5—V1 | 30.78 (4) |
O10—V1—V5 | 38.89 (6) | O4—V5—V1 | 42.55 (4) |
O2—V1—V5 | 145.73 (6) | V3—V5—V1 | 91.161 (15) |
O3—V1—V5 | 90.92 (5) | O14—V5—V2 | 135.15 (6) |
O1—V1—V5 | 89.40 (5) | O12—V5—V2 | 81.78 (5) |
O4—V1—V5 | 48.90 (4) | O11—V5—V2 | 33.03 (5) |
O4i—V1—V5 | 126.74 (5) | O13—V5—V2 | 123.12 (5) |
V3i—V1—V5 | 175.589 (16) | O10—V5—V2 | 81.81 (5) |
O10—V1—V4 | 85.41 (5) | O4—V5—V2 | 45.86 (4) |
O2—V1—V4 | 134.78 (6) | V3—V5—V2 | 60.280 (12) |
O3—V1—V4 | 37.40 (5) | V1—V5—V2 | 61.918 (13) |
O1—V1—V4 | 126.47 (5) | O14—V5—V4 | 133.05 (7) |
O4—V1—V4 | 46.09 (4) | O12—V5—V4 | 82.80 (6) |
O4i—V1—V4 | 85.41 (4) | O11—V5—V4 | 124.00 (5) |
V3i—V1—V4 | 118.764 (17) | O13—V5—V4 | 31.67 (5) |
V5—V1—V4 | 60.097 (13) | O10—V5—V4 | 79.87 (5) |
O5—V2—O6 | 104.23 (8) | O4—V5—V4 | 45.99 (4) |
O5—V2—O11 | 101.53 (8) | V3—V5—V4 | 60.831 (13) |
O6—V2—O11 | 95.79 (7) | V1—V5—V4 | 60.193 (13) |
O5—V2—O3i | 99.57 (8) | V2—V5—V4 | 91.641 (15) |
O6—V2—O3i | 90.55 (7) | V1—O1—V2 | 106.45 (7) |
O11—V2—O3i | 155.70 (8) | V1—O1—V4i | 107.77 (8) |
O5—V2—O1 | 98.25 (8) | V2—O1—V4i | 98.70 (7) |
O6—V2—O1 | 155.49 (7) | V1—O2—V3i | 110.40 (8) |
O11—V2—O1 | 89.06 (7) | V1—O3—V4 | 106.35 (8) |
O3i—V2—O1 | 76.06 (7) | V1—O3—V2i | 107.28 (7) |
O5—V2—O4 | 173.15 (8) | V4—O3—V2i | 102.06 (7) |
O6—V2—O4 | 81.58 (7) | V1—O4—V1i | 102.15 (7) |
O11—V2—O4 | 81.24 (7) | V1—O4—V2 | 94.87 (6) |
O3i—V2—O4 | 76.52 (6) | V1i—O4—V2 | 92.48 (6) |
O1—V2—O4 | 75.43 (6) | V1—O4—V4 | 91.62 (6) |
O5—V2—V4i | 89.16 (6) | V1i—O4—V4 | 94.91 (6) |
O6—V2—V4i | 129.12 (6) | V2—O4—V4 | 168.93 (8) |
O11—V2—V4i | 129.80 (6) | V1—O4—V3 | 170.91 (8) |
O3i—V2—V4i | 38.57 (5) | V1i—O4—V3 | 86.88 (5) |
O1—V2—V4i | 40.74 (4) | V2—O4—V3 | 85.71 (6) |
O4—V2—V4i | 84.30 (4) | V4—O4—V3 | 86.47 (5) |
O5—V2—V3 | 137.79 (6) | V1—O4—V5 | 88.55 (6) |
O6—V2—V3 | 33.68 (5) | V1i—O4—V5 | 169.26 (8) |
O11—V2—V3 | 85.24 (5) | V2—O4—V5 | 85.66 (6) |
O3i—V2—V3 | 87.21 (5) | V4—O4—V5 | 85.54 (5) |
O1—V2—V3 | 123.67 (5) | V3—O4—V5 | 82.44 (5) |
O4—V2—V3 | 48.30 (4) | V2—O6—V3 | 114.74 (9) |
V4i—V2—V3 | 118.392 (17) | V3—O8—V4 | 114.24 (8) |
O5—V2—V5 | 134.98 (6) | V1—O10—V5 | 110.33 (8) |
O6—V2—V5 | 83.35 (5) | V2—O11—V5 | 113.33 (9) |
O11—V2—V5 | 33.64 (5) | V5—O12—V3 | 113.47 (9) |
O3i—V2—V5 | 124.99 (5) | V4—O13—V5 | 114.29 (8) |
O1—V2—V5 | 87.66 (5) | N2—C1—C5 | 110.5 (2) |
O4—V2—V5 | 48.48 (4) | N2—C1—C9 | 131.1 (2) |
V4i—V2—V5 | 120.589 (17) | C5—C1—C9 | 118.4 (2) |
V3—V2—V5 | 59.223 (12) | C3—N2—C1 | 103.81 (19) |
O7—V3—O12 | 103.63 (8) | N2—C3—N4 | 113.2 (2) |
O7—V3—O8 | 101.95 (8) | N2—C3—H3 | 123.4 |
O12—V3—O8 | 91.70 (7) | N4—C3—H3 | 123.4 |
O7—V3—O6 | 102.24 (8) | C5—N4—C3 | 106.59 (19) |
O12—V3—O6 | 89.57 (7) | C5—N4—H4 | 126.7 |
O8—V3—O6 | 154.76 (7) | C3—N4—H4 | 126.7 |
O7—V3—O2i | 99.40 (8) | N4—C5—N6 | 127.1 (2) |
O12—V3—O2i | 156.92 (7) | N4—C5—C1 | 106.0 (2) |
O8—V3—O2i | 84.76 (7) | N6—C5—C1 | 126.9 (2) |
O6—V3—O2i | 84.27 (7) | C7—N6—C5 | 112.4 (2) |
O7—V3—O4 | 174.65 (8) | N6—C7—N8 | 124.7 (2) |
O12—V3—O4 | 81.70 (6) | N6—C7—H7 | 117.6 |
O8—V3—O4 | 78.04 (6) | N8—C7—H7 | 117.6 |
O6—V3—O4 | 77.21 (6) | C9—N8—C7 | 124.2 (2) |
O2i—V3—O4 | 75.25 (6) | C9—N8—H8 | 117.9 |
O7—V3—V1i | 130.64 (7) | C7—N8—H8 | 117.9 |
O12—V3—V1i | 125.70 (5) | N10—C9—N8 | 120.9 (2) |
O8—V3—V1i | 79.96 (5) | N10—C9—C1 | 125.8 (2) |
O6—V3—V1i | 78.88 (5) | N8—C9—C1 | 113.3 (2) |
O2i—V3—V1i | 31.24 (5) | C9—N10—H10A | 120.0 |
O4—V3—V1i | 44.01 (4) | C9—N10—H10B | 120.0 |
O7—V3—V5 | 136.40 (7) | H10A—N10—H10B | 120.0 |
O12—V3—V5 | 32.76 (5) | N12—C11—C15 | 110.3 (2) |
O8—V3—V5 | 84.57 (5) | N12—C11—C19 | 131.6 (2) |
O6—V3—V5 | 82.94 (5) | C15—C11—C19 | 118.1 (2) |
O2i—V3—V5 | 124.19 (5) | C13—N12—C11 | 104.13 (19) |
O4—V3—V5 | 48.94 (4) | N12—C13—N14 | 113.2 (2) |
V1i—V3—V5 | 92.951 (15) | N12—C13—H13 | 123.4 |
O7—V3—V2 | 133.79 (7) | N14—C13—H13 | 123.4 |
O12—V3—V2 | 81.29 (5) | C15—N14—C13 | 106.52 (19) |
O8—V3—V2 | 124.02 (5) | C15—N14—H14 | 126.7 |
O6—V3—V2 | 31.59 (5) | C13—N14—H14 | 126.7 |
O2i—V3—V2 | 81.87 (5) | N14—C15—N16 | 127.8 (2) |
O4—V3—V2 | 45.99 (4) | N14—C15—C11 | 105.9 (2) |
V1i—V3—V2 | 61.581 (13) | N16—C15—C11 | 126.3 (2) |
V5—V3—V2 | 60.497 (12) | C17—N16—C15 | 112.3 (2) |
O9—V4—O13 | 103.54 (8) | N16—C17—N18 | 126.4 (2) |
O9—V4—O8 | 102.14 (8) | N16—C17—H17 | 116.8 |
O13—V4—O8 | 94.40 (8) | N18—C17—H17 | 116.8 |
O9—V4—O3 | 99.69 (8) | C17—N18—C19 | 122.2 (2) |
O13—V4—O3 | 93.29 (7) | C17—N18—H18 | 118.9 |
O8—V4—O3 | 154.42 (7) | C19—N18—H18 | 118.9 |
O9—V4—O1i | 98.67 (8) | N20—C19—N18 | 120.7 (2) |
O13—V4—O1i | 156.90 (7) | N20—C19—C11 | 124.6 (2) |
O8—V4—O1i | 87.02 (7) | N18—C19—C11 | 114.7 (2) |
O3—V4—O1i | 76.63 (7) | C19—N20—H20A | 120.0 |
O9—V4—O4 | 173.70 (8) | C19—N20—H20B | 120.0 |
O13—V4—O4 | 82.08 (7) | H20A—N20—H20B | 120.0 |
O8—V4—O4 | 80.05 (6) | C25—C21—N22 | 110.1 (2) |
O3—V4—O4 | 76.91 (6) | C25—C21—C29 | 118.5 (2) |
O1i—V4—O4 | 75.45 (6) | N22—C21—C29 | 131.4 (2) |
O9—V4—V2i | 89.40 (6) | C23—N22—C21 | 103.96 (18) |
O13—V4—V2i | 132.64 (5) | N22—C23—N24 | 113.4 (2) |
O8—V4—V2i | 127.56 (5) | N22—C23—H23 | 123.3 |
O3—V4—V2i | 39.37 (5) | N24—C23—H23 | 123.3 |
O1i—V4—V2i | 40.55 (5) | C25—N24—C23 | 106.31 (19) |
O4—V4—V2i | 84.63 (4) | C25—N24—H24 | 126.8 |
O9—V4—V5 | 137.38 (6) | C23—N24—H24 | 126.8 |
O13—V4—V5 | 34.04 (5) | N24—C25—N26 | 127.6 (2) |
O8—V4—V5 | 83.33 (5) | N24—C25—C21 | 106.3 (2) |
O3—V4—V5 | 89.59 (5) | N26—C25—C21 | 126.1 (2) |
O1i—V4—V5 | 123.92 (5) | C27—N26—C25 | 111.7 (2) |
O4—V4—V5 | 48.47 (4) | N26—C27—N28 | 127.2 (2) |
V2i—V4—V5 | 120.850 (16) | N26—C27—H27 | 116.4 |
O9—V4—V1 | 135.32 (6) | N28—C27—H27 | 116.4 |
O13—V4—V1 | 79.03 (5) | C27—N28—C29 | 121.6 (2) |
O8—V4—V1 | 122.32 (5) | C27—N28—H28 | 119.2 |
O3—V4—V1 | 36.25 (5) | C29—N28—H28 | 119.2 |
O1i—V4—V1 | 80.77 (5) | N30—C29—N28 | 120.4 (2) |
O4—V4—V1 | 42.30 (4) | N30—C29—C21 | 124.8 (2) |
V2i—V4—V1 | 61.235 (13) | N28—C29—C21 | 114.8 (2) |
V5—V4—V1 | 59.711 (13) | C29—N30—H30A | 120.0 |
O14—V5—O12 | 104.19 (8) | C29—N30—H30B | 120.0 |
O14—V5—O11 | 102.27 (8) | H30A—N30—H30B | 120.0 |
O12—V5—O11 | 92.85 (7) | H1WA—O1W—H1WB | 108.0 |
O14—V5—O13 | 101.38 (8) | H2WA—O2W—H2WB | 104.2 |
O12—V5—O13 | 91.31 (7) | | |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2ii | 0.95 | 2.52 | 3.163 (3) | 125 |
C3—H3···O6iii | 0.95 | 2.46 | 3.390 (3) | 166 |
N4—H4···N16iv | 0.88 | 2.05 | 2.897 (3) | 162 |
C7—H7···O14v | 0.95 | 2.29 | 3.092 (3) | 142 |
N8—H8···O1W | 0.88 | 1.86 | 2.707 (3) | 160 |
N10—H10A···O2W | 0.88 | 2.01 | 2.863 (3) | 164 |
N10—H10B···N12 | 0.88 | 2.03 | 2.876 (3) | 161 |
C13—H13···O7 | 0.95 | 2.55 | 3.129 (3) | 120 |
C13—H13···O14vi | 0.95 | 2.57 | 3.189 (3) | 123 |
N14—H14···N6vii | 0.88 | 2.06 | 2.909 (3) | 161 |
C17—H17···O7viii | 0.95 | 2.39 | 3.180 (3) | 140 |
N20—H20A···O5iii | 0.88 | 2.07 | 2.904 (3) | 158 |
N20—H20B···N2 | 0.88 | 2.05 | 2.894 (3) | 160 |
C23—H23···O10ix | 0.95 | 2.46 | 3.106 (3) | 125 |
C23—H23···O13ix | 0.95 | 2.41 | 3.237 (3) | 146 |
N24—H24···N26ix | 0.88 | 2.03 | 2.873 (3) | 159 |
C27—H27···O10 | 0.95 | 2.56 | 3.354 (3) | 141 |
N30—H30A···O9iv | 0.88 | 2.12 | 2.951 (3) | 157 |
N30—H30B···N22x | 0.88 | 2.06 | 2.905 (3) | 160 |
O1W—H1WA···O5v | 0.83 | 2.50 | 3.211 (2) | 145.2 |
O1W—H1WB···O11 | 0.85 | 1.96 | 2.789 (3) | 167.7 |
O2W—H2WA···O12 | 0.84 | 2.10 | 2.905 (3) | 159.4 |
O2W—H2WB···O13vi | 0.85 | 2.14 | 2.965 (2) | 163.9 |
Symmetry codes: (ii) x−1, y, z+1; (iii) −x+1, −y+1, −z+2; (iv) x, y−1, z; (v) −x+1, −y+1, −z+1; (vi) −x+1, −y+2, −z+1; (vii) x, y+1, z; (viii) −x+1, −y+2, −z+2; (ix) −x+2, −y+1, −z; (x) −x+2, −y, −z. |