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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520619016196/bm5122sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619016196/bm5122sup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520619016196/bm5122sup3.pdf
Synthesis optimization and clarification, bio-sensing feasibility, optical assessments in solution and biological assays

CCDC reference: 1910672

Computing details top

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).

(I) top
Crystal data top
O28V10·6(C5H6N5)·4(H2O)Z = 1
Mr = 1846.35F(000) = 920
Triclinic, P1Dx = 2.070 Mg m3
a = 11.3756 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.5611 (3) ÅCell parameters from 15803 reflections
c = 14.0894 (4) Åθ = 3.0–29.3°
α = 73.533 (2)°µ = 1.62 mm1
β = 67.176 (3)°T = 100 K
γ = 60.845 (3)°Parallelepiped, yellow
V = 1481.18 (9) Å30.14 × 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 tube5898 reflections with I > 2σ(I)
Detector resolution: 10.6249 pixels mm-1Rint = 0.039
ω–scanθmax = 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 = 1515
Tmin = 0.897, Tmax = 1.000k = 1515
48373 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: mixed
wR(F2) = 0.096H-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 parametersΔρmax = 1.42 e Å3
0 restraintsΔρmin = 0.53 e Å3
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
xyzUiso*/Ueq
V11.01943 (4)0.47426 (4)0.38479 (3)0.01774 (10)
V20.75387 (4)0.47450 (4)0.57856 (3)0.01838 (10)
V30.69263 (5)0.75569 (4)0.60968 (3)0.02034 (10)
V40.95368 (5)0.75566 (4)0.42078 (3)0.01902 (10)
V50.72245 (5)0.70485 (4)0.39759 (3)0.02039 (10)
O10.93212 (18)0.35794 (15)0.47808 (12)0.0193 (3)
O21.16007 (18)0.35347 (16)0.31411 (12)0.0202 (3)
O31.09951 (18)0.59900 (15)0.34858 (12)0.0192 (3)
O40.87397 (18)0.59893 (15)0.50036 (12)0.0193 (3)
O50.68471 (19)0.36891 (16)0.63157 (13)0.0228 (4)
O60.64651 (18)0.60822 (16)0.65738 (12)0.0208 (3)
O70.57573 (19)0.85740 (17)0.69275 (13)0.0245 (4)
O80.80903 (18)0.84110 (15)0.53320 (12)0.0204 (3)
O91.02660 (19)0.85762 (16)0.36718 (12)0.0218 (4)
O100.90196 (18)0.55684 (15)0.31664 (12)0.0203 (3)
O110.67744 (18)0.56156 (16)0.47033 (12)0.0213 (4)
O120.61171 (18)0.80470 (16)0.50419 (13)0.0219 (4)
O130.83868 (19)0.79814 (16)0.34624 (12)0.0215 (4)
O140.63272 (19)0.76768 (16)0.31643 (13)0.0247 (4)
C10.3475 (2)0.5426 (2)0.94107 (18)0.0165 (4)
N20.33193 (19)0.56925 (18)1.03605 (15)0.0175 (4)
C30.3258 (2)0.4621 (2)1.09959 (19)0.0194 (5)
H30.3159290.4508961.1713190.023*
N40.3353 (2)0.36916 (19)1.05160 (16)0.0213 (4)
H40.3325650.2920051.0807170.026*
C50.3496 (2)0.4191 (2)0.95025 (19)0.0195 (5)
N60.3611 (2)0.36092 (19)0.87352 (17)0.0224 (4)
C70.3726 (3)0.4351 (2)0.7835 (2)0.0237 (5)
H70.3829490.4007950.7255480.028*
N80.3708 (2)0.5584 (2)0.76725 (16)0.0213 (4)
H80.3783870.6008300.7040780.026*
C90.3581 (2)0.6196 (2)0.84274 (18)0.0170 (4)
N100.3541 (2)0.73872 (19)0.82210 (15)0.0190 (4)
H10A0.3596760.7805410.7588150.023*
H10B0.3459180.7771660.8714630.023*
C110.3241 (2)0.9367 (2)1.03888 (18)0.0175 (5)
N120.3366 (2)0.91061 (18)0.94480 (15)0.0178 (4)
C130.3480 (2)1.0144 (2)0.8799 (2)0.0212 (5)
H130.3580901.0244720.8082690.025*
N140.3438 (2)1.10636 (18)0.92609 (16)0.0212 (4)
H140.3499201.1818720.8957630.025*
C150.3283 (2)1.0583 (2)1.0277 (2)0.0200 (5)
N160.3180 (2)1.1157 (2)1.10425 (18)0.0246 (5)
C170.3007 (3)1.0437 (2)1.1949 (2)0.0249 (5)
H170.2925551.0779611.2520680.030*
N180.2932 (2)0.92530 (19)1.21491 (16)0.0217 (4)
H180.2813010.8853801.2789020.026*
C190.3036 (2)0.8657 (2)1.13908 (18)0.0184 (5)
N200.2930 (2)0.75192 (18)1.16150 (16)0.0210 (4)
H20A0.2790740.7133791.2258670.025*
H20B0.2998240.7144351.1121040.025*
C210.9884 (2)0.1981 (2)0.04875 (17)0.0154 (4)
N220.9991 (2)0.17174 (18)0.04524 (14)0.0164 (4)
C231.0092 (2)0.2759 (2)0.11035 (19)0.0188 (5)
H231.0175090.2862250.1816870.023*
N241.0065 (2)0.36801 (18)0.06514 (16)0.0199 (4)
H241.0126130.4434510.0958420.024*
C250.9926 (2)0.3197 (2)0.03639 (19)0.0180 (5)
N260.9839 (2)0.37757 (19)0.11230 (17)0.0220 (4)
C270.9709 (3)0.3035 (2)0.2022 (2)0.0240 (5)
H270.9641690.3377230.2589140.029*
N280.9662 (2)0.18378 (19)0.22311 (15)0.0194 (4)
H280.9572570.1429990.2868240.023*
C290.9750 (2)0.1248 (2)0.14763 (18)0.0165 (4)
N300.9707 (2)0.00817 (18)0.16995 (15)0.0185 (4)
H30A0.9621050.0322840.2337490.022*
H30B0.9763800.0293840.1210660.022*
O1W0.3885 (2)0.6393 (2)0.56410 (16)0.0380 (5)
H1WA0.3395070.6683190.5248310.057*
H1WB0.4737770.6174050.5271860.057*
O2W0.32070 (19)0.91226 (18)0.63433 (14)0.0306 (4)
H2WA0.3962950.8964850.5850780.046*
H2WB0.2902520.9935730.6409400.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
V10.0329 (2)0.01253 (18)0.01039 (19)0.01026 (17)0.00896 (16)0.00043 (14)
V20.0290 (2)0.01462 (19)0.0137 (2)0.01139 (17)0.00732 (16)0.00048 (14)
V30.0293 (2)0.0176 (2)0.0147 (2)0.00965 (17)0.00489 (17)0.00560 (15)
V40.0333 (2)0.01293 (19)0.01222 (19)0.01138 (17)0.00618 (17)0.00138 (14)
V50.0338 (2)0.01505 (19)0.0138 (2)0.01072 (17)0.00912 (17)0.00039 (14)
O10.0317 (9)0.0175 (8)0.0118 (8)0.0126 (7)0.0080 (7)0.0002 (6)
O20.0340 (10)0.0181 (8)0.0122 (8)0.0140 (7)0.0066 (7)0.0018 (6)
O30.0335 (9)0.0151 (8)0.0129 (8)0.0124 (7)0.0094 (7)0.0003 (6)
O40.0315 (9)0.0173 (8)0.0125 (8)0.0122 (7)0.0081 (7)0.0009 (6)
O50.0355 (10)0.0192 (8)0.0187 (9)0.0152 (8)0.0095 (7)0.0004 (7)
O60.0294 (9)0.0185 (8)0.0147 (8)0.0114 (7)0.0046 (7)0.0030 (6)
O70.0319 (10)0.0226 (9)0.0200 (9)0.0115 (8)0.0048 (7)0.0085 (7)
O80.0327 (9)0.0151 (8)0.0143 (8)0.0108 (7)0.0063 (7)0.0029 (6)
O90.0372 (10)0.0159 (8)0.0150 (8)0.0134 (7)0.0087 (7)0.0004 (6)
O100.0356 (10)0.0172 (8)0.0135 (8)0.0141 (7)0.0099 (7)0.0004 (6)
O110.0335 (10)0.0166 (8)0.0159 (8)0.0113 (7)0.0095 (7)0.0006 (6)
O120.0314 (9)0.0157 (8)0.0184 (8)0.0081 (7)0.0090 (7)0.0031 (6)
O130.0363 (10)0.0169 (8)0.0145 (8)0.0131 (7)0.0084 (7)0.0017 (6)
O140.0399 (11)0.0175 (8)0.0198 (9)0.0121 (8)0.0135 (8)0.0001 (7)
C10.0114 (10)0.0139 (10)0.0230 (12)0.0052 (8)0.0046 (9)0.0016 (9)
N20.0145 (9)0.0161 (9)0.0180 (10)0.0072 (8)0.0010 (8)0.0008 (7)
C30.0148 (11)0.0157 (11)0.0229 (12)0.0059 (9)0.0038 (9)0.0007 (9)
N40.0206 (10)0.0139 (9)0.0284 (11)0.0090 (8)0.0075 (9)0.0024 (8)
C50.0118 (10)0.0138 (10)0.0299 (13)0.0042 (9)0.0039 (9)0.0040 (9)
N60.0198 (10)0.0174 (10)0.0308 (12)0.0084 (8)0.0055 (9)0.0059 (8)
C70.0216 (12)0.0205 (12)0.0324 (14)0.0112 (10)0.0057 (10)0.0070 (10)
N80.0239 (11)0.0228 (10)0.0214 (10)0.0149 (9)0.0027 (8)0.0050 (8)
C90.0123 (10)0.0190 (11)0.0203 (12)0.0084 (9)0.0025 (9)0.0034 (9)
N100.0233 (10)0.0193 (10)0.0159 (10)0.0130 (8)0.0033 (8)0.0004 (7)
C110.0129 (10)0.0143 (10)0.0241 (12)0.0047 (9)0.0045 (9)0.0043 (9)
N120.0157 (9)0.0146 (9)0.0213 (10)0.0070 (8)0.0034 (8)0.0013 (7)
C130.0180 (11)0.0147 (11)0.0255 (13)0.0063 (9)0.0031 (10)0.0012 (9)
N140.0149 (9)0.0115 (9)0.0318 (12)0.0059 (8)0.0022 (8)0.0014 (8)
C150.0115 (10)0.0131 (10)0.0332 (14)0.0028 (9)0.0064 (10)0.0042 (9)
N160.0177 (10)0.0175 (10)0.0400 (13)0.0063 (8)0.0091 (9)0.0069 (9)
C170.0214 (12)0.0193 (12)0.0377 (15)0.0065 (10)0.0118 (11)0.0084 (11)
N180.0261 (11)0.0182 (10)0.0217 (10)0.0081 (8)0.0104 (9)0.0014 (8)
C190.0165 (11)0.0153 (11)0.0224 (12)0.0047 (9)0.0063 (9)0.0040 (9)
N200.0282 (11)0.0137 (9)0.0197 (10)0.0080 (8)0.0092 (9)0.0011 (8)
C210.0129 (10)0.0140 (10)0.0179 (11)0.0053 (8)0.0017 (8)0.0049 (8)
N220.0170 (9)0.0136 (9)0.0163 (9)0.0072 (8)0.0012 (8)0.0027 (7)
C230.0171 (11)0.0129 (10)0.0222 (12)0.0066 (9)0.0011 (9)0.0024 (9)
N240.0179 (10)0.0108 (9)0.0292 (11)0.0077 (8)0.0047 (8)0.0001 (8)
C250.0120 (10)0.0135 (10)0.0273 (13)0.0035 (9)0.0040 (9)0.0069 (9)
N260.0181 (10)0.0147 (9)0.0348 (12)0.0059 (8)0.0081 (9)0.0070 (8)
C270.0278 (13)0.0187 (12)0.0288 (13)0.0096 (10)0.0092 (11)0.0069 (10)
N280.0269 (11)0.0177 (9)0.0159 (10)0.0097 (8)0.0068 (8)0.0042 (7)
C290.0154 (11)0.0164 (11)0.0190 (11)0.0050 (9)0.0060 (9)0.0059 (9)
N300.0246 (10)0.0169 (9)0.0150 (9)0.0109 (8)0.0039 (8)0.0022 (7)
O1W0.0386 (12)0.0442 (12)0.0334 (11)0.0154 (10)0.0142 (9)0.0068 (9)
O2W0.0304 (10)0.0229 (9)0.0295 (10)0.0049 (8)0.0093 (8)0.0022 (8)
Geometric parameters (Å, º) top
V1—O101.6887 (17)N6—C71.313 (3)
V1—O21.6962 (17)C7—N81.369 (3)
V1—O31.9163 (16)C7—H70.9500
V1—O11.9517 (16)N8—C91.364 (3)
V1—O42.0936 (16)N8—H80.8800
V1—O4i2.1334 (16)C9—N101.306 (3)
V1—V3i3.0657 (6)N10—H10A0.8800
V1—V53.0947 (6)N10—H10B0.8800
V1—V43.1098 (5)C11—N121.381 (3)
V2—O51.6217 (17)C11—C151.392 (3)
V2—O61.7878 (16)C11—C191.412 (3)
V2—O111.8440 (16)N12—C131.315 (3)
V2—O3i2.0025 (17)C13—N141.369 (3)
V2—O12.0307 (17)C13—H130.9500
V2—O42.2357 (16)N14—C151.356 (3)
V2—V4i3.0875 (6)N14—H140.8800
V2—V33.1000 (5)C15—N161.360 (3)
V2—V53.1066 (5)N16—C171.313 (3)
V3—O71.6031 (17)C17—N181.355 (3)
V3—O121.8581 (17)C17—H170.9500
V3—O81.8583 (17)N18—C191.368 (3)
V3—O61.8926 (17)N18—H180.8800
V3—O2i2.0300 (17)C19—N201.317 (3)
V3—O42.3211 (16)N20—H20A0.8800
V3—V53.0668 (6)N20—H20B0.8800
V4—O91.6155 (17)C21—C251.389 (3)
V4—O131.7897 (17)C21—N221.389 (3)
V4—O81.8637 (16)C21—C291.405 (3)
V4—O31.9685 (16)N22—C231.316 (3)
V4—O1i2.0385 (16)C23—N241.371 (3)
V4—O42.2412 (16)C23—H230.9500
V4—V53.1068 (6)N24—C251.357 (3)
V5—O141.6091 (17)N24—H240.8800
V5—O121.8094 (16)C25—N261.364 (3)
V5—O111.8744 (16)N26—C271.312 (3)
V5—O131.9079 (17)C27—N281.355 (3)
V5—O102.0721 (17)C27—H270.9500
V5—O42.3327 (16)N28—C291.367 (3)
C1—N21.383 (3)N28—H280.8800
C1—C51.386 (3)C29—N301.316 (3)
C1—C91.415 (3)N30—H30A0.8800
N2—C31.322 (3)N30—H30B0.8800
C3—N41.366 (3)O1W—H1WA0.8256
C3—H30.9500O1W—H1WB0.8479
N4—C51.357 (3)O2W—H2WA0.8427
N4—H40.8800O2W—H2WB0.8484
C5—N61.362 (3)
O10—V1—O2106.86 (8)O11—V5—O13154.17 (8)
O10—V1—O398.37 (7)O14—V5—O10100.09 (8)
O2—V1—O397.39 (8)O12—V5—O10155.69 (7)
O10—V1—O196.88 (8)O11—V5—O1082.96 (7)
O2—V1—O195.79 (7)O13—V5—O1082.81 (7)
O3—V1—O1155.99 (7)O14—V5—O4173.37 (8)
O10—V1—O487.79 (7)O12—V5—O482.37 (7)
O2—V1—O4165.26 (7)O11—V5—O478.04 (6)
O3—V1—O481.72 (7)O13—V5—O477.27 (6)
O1—V1—O480.46 (6)O10—V5—O473.33 (6)
O10—V1—O4i165.59 (7)O14—V5—V3137.94 (6)
O2—V1—O4i87.47 (7)O12—V5—V333.76 (5)
O3—V1—O4i80.84 (6)O11—V5—V385.72 (5)
O1—V1—O4i79.79 (6)O13—V5—V383.67 (5)
O4—V1—O4i77.85 (7)O10—V5—V3121.94 (5)
O10—V1—V3i145.21 (6)O4—V5—V348.61 (4)
O2—V1—V3i38.36 (6)O14—V5—V1130.86 (6)
O3—V1—V3i89.73 (5)O12—V5—V1124.92 (6)
O1—V1—V3i88.23 (5)O11—V5—V178.77 (5)
O4—V1—V3i126.95 (5)O13—V5—V177.97 (5)
O4i—V1—V3i49.11 (4)O10—V5—V130.78 (4)
O10—V1—V538.89 (6)O4—V5—V142.55 (4)
O2—V1—V5145.73 (6)V3—V5—V191.161 (15)
O3—V1—V590.92 (5)O14—V5—V2135.15 (6)
O1—V1—V589.40 (5)O12—V5—V281.78 (5)
O4—V1—V548.90 (4)O11—V5—V233.03 (5)
O4i—V1—V5126.74 (5)O13—V5—V2123.12 (5)
V3i—V1—V5175.589 (16)O10—V5—V281.81 (5)
O10—V1—V485.41 (5)O4—V5—V245.86 (4)
O2—V1—V4134.78 (6)V3—V5—V260.280 (12)
O3—V1—V437.40 (5)V1—V5—V261.918 (13)
O1—V1—V4126.47 (5)O14—V5—V4133.05 (7)
O4—V1—V446.09 (4)O12—V5—V482.80 (6)
O4i—V1—V485.41 (4)O11—V5—V4124.00 (5)
V3i—V1—V4118.764 (17)O13—V5—V431.67 (5)
V5—V1—V460.097 (13)O10—V5—V479.87 (5)
O5—V2—O6104.23 (8)O4—V5—V445.99 (4)
O5—V2—O11101.53 (8)V3—V5—V460.831 (13)
O6—V2—O1195.79 (7)V1—V5—V460.193 (13)
O5—V2—O3i99.57 (8)V2—V5—V491.641 (15)
O6—V2—O3i90.55 (7)V1—O1—V2106.45 (7)
O11—V2—O3i155.70 (8)V1—O1—V4i107.77 (8)
O5—V2—O198.25 (8)V2—O1—V4i98.70 (7)
O6—V2—O1155.49 (7)V1—O2—V3i110.40 (8)
O11—V2—O189.06 (7)V1—O3—V4106.35 (8)
O3i—V2—O176.06 (7)V1—O3—V2i107.28 (7)
O5—V2—O4173.15 (8)V4—O3—V2i102.06 (7)
O6—V2—O481.58 (7)V1—O4—V1i102.15 (7)
O11—V2—O481.24 (7)V1—O4—V294.87 (6)
O3i—V2—O476.52 (6)V1i—O4—V292.48 (6)
O1—V2—O475.43 (6)V1—O4—V491.62 (6)
O5—V2—V4i89.16 (6)V1i—O4—V494.91 (6)
O6—V2—V4i129.12 (6)V2—O4—V4168.93 (8)
O11—V2—V4i129.80 (6)V1—O4—V3170.91 (8)
O3i—V2—V4i38.57 (5)V1i—O4—V386.88 (5)
O1—V2—V4i40.74 (4)V2—O4—V385.71 (6)
O4—V2—V4i84.30 (4)V4—O4—V386.47 (5)
O5—V2—V3137.79 (6)V1—O4—V588.55 (6)
O6—V2—V333.68 (5)V1i—O4—V5169.26 (8)
O11—V2—V385.24 (5)V2—O4—V585.66 (6)
O3i—V2—V387.21 (5)V4—O4—V585.54 (5)
O1—V2—V3123.67 (5)V3—O4—V582.44 (5)
O4—V2—V348.30 (4)V2—O6—V3114.74 (9)
V4i—V2—V3118.392 (17)V3—O8—V4114.24 (8)
O5—V2—V5134.98 (6)V1—O10—V5110.33 (8)
O6—V2—V583.35 (5)V2—O11—V5113.33 (9)
O11—V2—V533.64 (5)V5—O12—V3113.47 (9)
O3i—V2—V5124.99 (5)V4—O13—V5114.29 (8)
O1—V2—V587.66 (5)N2—C1—C5110.5 (2)
O4—V2—V548.48 (4)N2—C1—C9131.1 (2)
V4i—V2—V5120.589 (17)C5—C1—C9118.4 (2)
V3—V2—V559.223 (12)C3—N2—C1103.81 (19)
O7—V3—O12103.63 (8)N2—C3—N4113.2 (2)
O7—V3—O8101.95 (8)N2—C3—H3123.4
O12—V3—O891.70 (7)N4—C3—H3123.4
O7—V3—O6102.24 (8)C5—N4—C3106.59 (19)
O12—V3—O689.57 (7)C5—N4—H4126.7
O8—V3—O6154.76 (7)C3—N4—H4126.7
O7—V3—O2i99.40 (8)N4—C5—N6127.1 (2)
O12—V3—O2i156.92 (7)N4—C5—C1106.0 (2)
O8—V3—O2i84.76 (7)N6—C5—C1126.9 (2)
O6—V3—O2i84.27 (7)C7—N6—C5112.4 (2)
O7—V3—O4174.65 (8)N6—C7—N8124.7 (2)
O12—V3—O481.70 (6)N6—C7—H7117.6
O8—V3—O478.04 (6)N8—C7—H7117.6
O6—V3—O477.21 (6)C9—N8—C7124.2 (2)
O2i—V3—O475.25 (6)C9—N8—H8117.9
O7—V3—V1i130.64 (7)C7—N8—H8117.9
O12—V3—V1i125.70 (5)N10—C9—N8120.9 (2)
O8—V3—V1i79.96 (5)N10—C9—C1125.8 (2)
O6—V3—V1i78.88 (5)N8—C9—C1113.3 (2)
O2i—V3—V1i31.24 (5)C9—N10—H10A120.0
O4—V3—V1i44.01 (4)C9—N10—H10B120.0
O7—V3—V5136.40 (7)H10A—N10—H10B120.0
O12—V3—V532.76 (5)N12—C11—C15110.3 (2)
O8—V3—V584.57 (5)N12—C11—C19131.6 (2)
O6—V3—V582.94 (5)C15—C11—C19118.1 (2)
O2i—V3—V5124.19 (5)C13—N12—C11104.13 (19)
O4—V3—V548.94 (4)N12—C13—N14113.2 (2)
V1i—V3—V592.951 (15)N12—C13—H13123.4
O7—V3—V2133.79 (7)N14—C13—H13123.4
O12—V3—V281.29 (5)C15—N14—C13106.52 (19)
O8—V3—V2124.02 (5)C15—N14—H14126.7
O6—V3—V231.59 (5)C13—N14—H14126.7
O2i—V3—V281.87 (5)N14—C15—N16127.8 (2)
O4—V3—V245.99 (4)N14—C15—C11105.9 (2)
V1i—V3—V261.581 (13)N16—C15—C11126.3 (2)
V5—V3—V260.497 (12)C17—N16—C15112.3 (2)
O9—V4—O13103.54 (8)N16—C17—N18126.4 (2)
O9—V4—O8102.14 (8)N16—C17—H17116.8
O13—V4—O894.40 (8)N18—C17—H17116.8
O9—V4—O399.69 (8)C17—N18—C19122.2 (2)
O13—V4—O393.29 (7)C17—N18—H18118.9
O8—V4—O3154.42 (7)C19—N18—H18118.9
O9—V4—O1i98.67 (8)N20—C19—N18120.7 (2)
O13—V4—O1i156.90 (7)N20—C19—C11124.6 (2)
O8—V4—O1i87.02 (7)N18—C19—C11114.7 (2)
O3—V4—O1i76.63 (7)C19—N20—H20A120.0
O9—V4—O4173.70 (8)C19—N20—H20B120.0
O13—V4—O482.08 (7)H20A—N20—H20B120.0
O8—V4—O480.05 (6)C25—C21—N22110.1 (2)
O3—V4—O476.91 (6)C25—C21—C29118.5 (2)
O1i—V4—O475.45 (6)N22—C21—C29131.4 (2)
O9—V4—V2i89.40 (6)C23—N22—C21103.96 (18)
O13—V4—V2i132.64 (5)N22—C23—N24113.4 (2)
O8—V4—V2i127.56 (5)N22—C23—H23123.3
O3—V4—V2i39.37 (5)N24—C23—H23123.3
O1i—V4—V2i40.55 (5)C25—N24—C23106.31 (19)
O4—V4—V2i84.63 (4)C25—N24—H24126.8
O9—V4—V5137.38 (6)C23—N24—H24126.8
O13—V4—V534.04 (5)N24—C25—N26127.6 (2)
O8—V4—V583.33 (5)N24—C25—C21106.3 (2)
O3—V4—V589.59 (5)N26—C25—C21126.1 (2)
O1i—V4—V5123.92 (5)C27—N26—C25111.7 (2)
O4—V4—V548.47 (4)N26—C27—N28127.2 (2)
V2i—V4—V5120.850 (16)N26—C27—H27116.4
O9—V4—V1135.32 (6)N28—C27—H27116.4
O13—V4—V179.03 (5)C27—N28—C29121.6 (2)
O8—V4—V1122.32 (5)C27—N28—H28119.2
O3—V4—V136.25 (5)C29—N28—H28119.2
O1i—V4—V180.77 (5)N30—C29—N28120.4 (2)
O4—V4—V142.30 (4)N30—C29—C21124.8 (2)
V2i—V4—V161.235 (13)N28—C29—C21114.8 (2)
V5—V4—V159.711 (13)C29—N30—H30A120.0
O14—V5—O12104.19 (8)C29—N30—H30B120.0
O14—V5—O11102.27 (8)H30A—N30—H30B120.0
O12—V5—O1192.85 (7)H1WA—O1W—H1WB108.0
O14—V5—O13101.38 (8)H2WA—O2W—H2WB104.2
O12—V5—O1391.31 (7)
Symmetry code: (i) x+2, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O2ii0.952.523.163 (3)125
C3—H3···O6iii0.952.463.390 (3)166
N4—H4···N16iv0.882.052.897 (3)162
C7—H7···O14v0.952.293.092 (3)142
N8—H8···O1W0.881.862.707 (3)160
N10—H10A···O2W0.882.012.863 (3)164
N10—H10B···N120.882.032.876 (3)161
C13—H13···O70.952.553.129 (3)120
C13—H13···O14vi0.952.573.189 (3)123
N14—H14···N6vii0.882.062.909 (3)161
C17—H17···O7viii0.952.393.180 (3)140
N20—H20A···O5iii0.882.072.904 (3)158
N20—H20B···N20.882.052.894 (3)160
C23—H23···O10ix0.952.463.106 (3)125
C23—H23···O13ix0.952.413.237 (3)146
N24—H24···N26ix0.882.032.873 (3)159
C27—H27···O100.952.563.354 (3)141
N30—H30A···O9iv0.882.122.951 (3)157
N30—H30B···N22x0.882.062.905 (3)160
O1W—H1WA···O5v0.832.503.211 (2)145.2
O1W—H1WB···O110.851.962.789 (3)167.7
O2W—H2WA···O120.842.102.905 (3)159.4
O2W—H2WB···O13vi0.852.142.965 (2)163.9
Symmetry codes: (ii) x1, y, z+1; (iii) x+1, y+1, z+2; (iv) x, y1, 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.
 

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