Download citation
Download citation
link to html
Valinomycin is a naturally occurring cyclic dodecadepsipeptide with the formula cyclo-[D-HiVA[rightwards arrow]L-Val [rightwards arrow]L-LA[rightwards arrow]L-Val]3 (D-HiVA is D-[alpha]-hy­droxy­isovaleic acid, Val is valine and LA is lactic acid), which binds a K+ ion with high selectively. In the past, several cation-binding modes have been revealed by X-ray crystallography. In the K+, Rb+ and Cs+ complexes, the ester O atoms coordinate the cation with a trigonal anti­prismatic geometry, while the six amide groups form intra­molecular hydrogen bonds and the network that is formed has a bracelet-like conformation (Type 1 binding). Type 2 binding is seen with the Na+ cation, in which the valinomycin molecule retains the bracelet conformation but the cations are coordinated by only three ester carbonyl groups and are not centrally located. In addition, a picrate counter-ion and a water mol­ecule is found at the center of the valinomycin bracelet. Type 3 binding is observed with divalent Ba2+, in which two cations are incorporated, bridged by two anions, and coordinated by amide carbonyl groups, and there are no intra­molecular amide hydrogen bonds. In this paper, we present a new Type 4 cation-binding mode, observed in valinomycin hexa­aqua­magnesium bis­(tri­fluoro­methane­sulfonate) trihydrate, C54H90N6O18·[Mg(H2O)6](CF3SO3)2·3H2O, in which the valinomycin molecule incorporates a whole hexa­aqua­magnesium ion, [Mg(H2O)6]2+, via hydrogen bonding between the amide carbonyl groups and the hydrate water H atoms. In this complex, valinomycin retains the threefold symmetry observed in Type 1 binding, but the amide hydrogen-bond network is lost; the hexa­aqua­magnesium cation is hydrogen bonded by six amide carbonyl groups. 1H NMR titration data is consistent with the 1:1 binding stoichiometry in aceto­nitrile solution. This new cation-binding mode of binding a whole hexa­aqua­magnesium ion by a cyclic polypeptide is likely to have important implications for the study of metal binding with biological models under physiological conditions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616010676/qs3057sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616010676/qs3057Isup2.hkl
Contains datablock I

mol

MDL mol file https://doi.org/10.1107/S2053229616010676/qs3057Isup3.mol
Supplementary material

CCDC reference: 1489496

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Valinomycin hexaaquamagnesium bis(trifluoromethanesulfonate) trihydrate top
Crystal data top
C54H90N6O18·[Mg(H2O)6](CF3O3S)2·3H2ODx = 1.284 Mg m3
Mr = 1595.91Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3Cell parameters from 9973 reflections
a = 16.4188 (5) Åθ = 2.5–31.5°
c = 8.8395 (3) ŵ = 0.16 mm1
V = 2063.67 (14) Å3T = 100 K
Z = 1Prism, colourless
F(000) = 8480.66 × 0.46 × 0.24 mm
Data collection top
Bruker APEXII CCD
diffractometer
8681 independent reflections
Radiation source: fine-focus sealed tube7479 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 512 pixels mm-1θmax = 31.5°, θmin = 1.4°
φ and ω scansh = 2319
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
k = 2324
Tmin = 0.642, Tmax = 0.746l = 1212
19702 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.047 w = 1/[σ2(Fo2) + (0.0586P)2 + 0.5419P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.120(Δ/σ)max = 0.006
S = 1.04Δρmax = 0.42 e Å3
8681 reflectionsΔρmin = 0.28 e Å3
324 parametersAbsolute structure: Flack x determined using 3081 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013); Hooft y determined using 4154 Bijvoet pairs (Hooft et al., 2008)
10 restraintsAbsolute structure parameter: 0.08 (4)
Special details top

Experimental. SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1337 before and 0.0601 after correction. The Ratio of minimum to maximum transmission is 0.8598. The λ/2 correction factor is 0.00150.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.66670.33330.66117 (12)0.0184 (2)
F10.60558 (17)0.35704 (17)0.9207 (2)0.0438 (5)
O10.69848 (16)0.43012 (16)0.6250 (3)0.0285 (5)
C10.66670.33330.8658 (6)0.0265 (10)
S21.00001.00000.30056 (11)0.01403 (19)
F20.91560 (14)0.93744 (14)0.0403 (2)0.0336 (4)
O20.93719 (14)1.03489 (14)0.3376 (2)0.0204 (4)
C21.00001.00000.0944 (5)0.0222 (9)
Mg10.33330.66670.44311 (17)0.0187 (3)
H4A0.2937 (14)0.5084 (13)0.587 (5)0.060 (10)*
H4B0.4026 (16)0.567 (2)0.559 (4)0.060 (10)*
O30.44327 (15)0.67964 (16)0.3086 (3)0.0282 (5)
H3A0.5057 (11)0.725 (2)0.333 (3)0.042*
H3B0.4351 (19)0.671 (3)0.2020 (16)0.042*
O40.34675 (16)0.57098 (16)0.5779 (3)0.0319 (5)
O50.39800 (13)0.41075 (14)0.6719 (2)0.0205 (4)
O60.40520 (14)0.34550 (14)0.4513 (2)0.0222 (4)
O70.50107 (16)0.56902 (15)0.4816 (3)0.0287 (5)
O80.67291 (13)0.73269 (13)0.2606 (2)0.0192 (4)
O90.59991 (15)0.82266 (16)0.4373 (3)0.0352 (6)
O100.72909 (15)0.73641 (14)0.4949 (2)0.0261 (5)
N10.61651 (16)0.53350 (16)0.4809 (3)0.0195 (4)
H10.64060.50190.52360.023*
N20.74635 (16)0.94657 (16)0.4611 (3)0.0186 (4)
H20.80330.97770.42280.022*
C30.36146 (19)0.34741 (19)0.5583 (3)0.0174 (5)
C40.49917 (19)0.4676 (2)0.6805 (3)0.0211 (5)
H40.52730.42640.69490.025*
C50.53817 (19)0.52612 (19)0.5368 (3)0.0204 (5)
C60.66311 (19)0.59238 (18)0.3489 (3)0.0185 (5)
H60.61920.56910.26060.022*
C70.69074 (19)0.69393 (19)0.3818 (3)0.0188 (5)
C80.71813 (19)0.83473 (18)0.2629 (3)0.0202 (5)
H80.78780.86250.27020.024*
C90.68318 (19)0.86665 (19)0.3973 (3)0.0210 (5)
C100.72384 (18)0.98310 (19)0.5948 (3)0.0173 (5)
H100.69640.93240.67310.021*
C110.8147 (2)1.0665 (2)0.6580 (3)0.0223 (5)
H110.84831.11130.57330.027*
C120.8787 (2)1.0314 (3)0.7201 (4)0.0329 (7)
H12A0.84720.98800.80430.049*
H12B0.93771.08500.75580.049*
H12C0.89220.99860.63990.049*
C130.7937 (2)1.1190 (2)0.7812 (4)0.0336 (7)
H13A0.75931.14760.73700.050*
H13B0.85301.16820.82470.050*
H13C0.75551.07470.86070.050*
C140.6938 (2)0.8632 (2)0.1151 (4)0.0301 (6)
H14A0.71500.83960.03090.045*
H14B0.72500.93200.10960.045*
H14C0.62550.83660.10870.045*
C150.75134 (19)0.58643 (18)0.3117 (3)0.0191 (5)
H150.78680.59520.40800.023*
C160.7239 (2)0.4894 (2)0.2484 (4)0.0280 (6)
H16A0.78060.48460.23430.042*
H16B0.69210.48060.15090.042*
H16C0.68140.44080.31940.042*
C170.8166 (2)0.6631 (2)0.2011 (3)0.0271 (6)
H17A0.87200.65700.18130.041*
H17B0.83640.72510.24510.041*
H17C0.78310.65640.10600.041*
C180.5194 (2)0.5312 (2)0.8198 (3)0.0296 (6)
H180.49140.57210.80100.035*
C190.6254 (2)0.5952 (3)0.8420 (4)0.0375 (7)
H19A0.65500.55660.85590.056*
H19B0.63680.63460.93160.056*
H19C0.65220.63530.75270.056*
C200.4742 (3)0.4738 (3)0.9613 (4)0.0430 (9)
H20A0.40610.43510.94590.064*
H20B0.48660.51631.04710.064*
H20C0.50060.43310.98230.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0195 (3)0.0195 (3)0.0164 (5)0.00973 (16)0.0000.000
F10.0497 (14)0.0575 (14)0.0289 (10)0.0304 (12)0.0095 (9)0.0088 (9)
O10.0300 (12)0.0229 (10)0.0316 (11)0.0126 (9)0.0047 (9)0.0055 (8)
C10.0315 (16)0.0315 (16)0.016 (2)0.0158 (8)0.0000.000
S20.0134 (3)0.0134 (3)0.0152 (4)0.00671 (14)0.0000.000
F20.0307 (10)0.0400 (11)0.0225 (9)0.0120 (9)0.0100 (7)0.0052 (8)
O20.0173 (9)0.0204 (9)0.0250 (9)0.0107 (8)0.0037 (7)0.0002 (7)
C20.0248 (15)0.0248 (15)0.017 (2)0.0124 (7)0.0000.000
Mg10.0130 (4)0.0130 (4)0.0301 (9)0.00652 (19)0.0000.000
O30.0173 (9)0.0309 (11)0.0354 (11)0.0112 (9)0.0015 (8)0.0006 (9)
O40.0283 (11)0.0263 (11)0.0436 (13)0.0156 (9)0.0039 (9)0.0054 (9)
O50.0134 (8)0.0220 (9)0.0239 (9)0.0074 (7)0.0026 (7)0.0050 (7)
O60.0174 (9)0.0208 (10)0.0261 (10)0.0078 (8)0.0010 (7)0.0023 (8)
O70.0243 (10)0.0237 (11)0.0420 (12)0.0149 (9)0.0021 (9)0.0035 (9)
O80.0184 (9)0.0117 (8)0.0250 (9)0.0056 (7)0.0027 (7)0.0009 (7)
O90.0151 (10)0.0256 (11)0.0528 (14)0.0010 (9)0.0104 (9)0.0101 (10)
O100.0284 (11)0.0183 (10)0.0266 (10)0.0080 (9)0.0070 (8)0.0060 (8)
N10.0157 (10)0.0170 (11)0.0252 (11)0.0078 (9)0.0033 (8)0.0003 (8)
N20.0130 (10)0.0139 (10)0.0280 (11)0.0059 (8)0.0052 (8)0.0003 (8)
C30.0153 (11)0.0168 (11)0.0219 (12)0.0094 (9)0.0028 (9)0.0001 (9)
C40.0126 (11)0.0237 (13)0.0245 (12)0.0071 (10)0.0034 (9)0.0015 (10)
C50.0180 (12)0.0145 (12)0.0267 (13)0.0066 (10)0.0058 (10)0.0030 (9)
C60.0189 (12)0.0129 (11)0.0206 (12)0.0056 (10)0.0079 (9)0.0026 (9)
C70.0160 (12)0.0139 (11)0.0237 (12)0.0054 (9)0.0008 (9)0.0001 (9)
C80.0170 (12)0.0106 (11)0.0294 (13)0.0042 (9)0.0023 (9)0.0000 (9)
C90.0132 (11)0.0140 (12)0.0343 (14)0.0057 (10)0.0038 (10)0.0005 (9)
C100.0159 (11)0.0158 (11)0.0215 (12)0.0090 (10)0.0027 (9)0.0023 (9)
C110.0215 (13)0.0216 (13)0.0223 (13)0.0096 (11)0.0033 (9)0.0003 (10)
C120.0295 (16)0.049 (2)0.0270 (14)0.0249 (15)0.0061 (12)0.0040 (13)
C130.0300 (16)0.0324 (16)0.0358 (16)0.0137 (13)0.0094 (12)0.0139 (13)
C140.0334 (16)0.0236 (14)0.0327 (15)0.0139 (13)0.0036 (12)0.0064 (11)
C150.0213 (12)0.0170 (12)0.0191 (11)0.0096 (10)0.0019 (9)0.0023 (9)
C160.0343 (16)0.0226 (14)0.0283 (14)0.0151 (12)0.0006 (12)0.0049 (11)
C170.0266 (15)0.0256 (14)0.0282 (14)0.0124 (12)0.0042 (11)0.0047 (11)
C180.0231 (14)0.0355 (16)0.0282 (14)0.0132 (13)0.0077 (11)0.0131 (12)
C190.0256 (15)0.0432 (19)0.0356 (16)0.0111 (14)0.0109 (12)0.0128 (14)
C200.0320 (17)0.064 (2)0.0268 (15)0.0199 (17)0.0032 (12)0.0098 (15)
Geometric parameters (Å, º) top
S1—O1i1.439 (2)C4—C181.539 (4)
S1—O11.439 (2)C6—H61.0000
S1—O1ii1.439 (2)C6—C71.521 (4)
S1—C11.809 (5)C6—C151.535 (4)
F1—C11.336 (3)C8—H81.0000
C1—F1ii1.336 (3)C8—C91.522 (4)
C1—F1i1.336 (3)C8—C141.507 (4)
S2—O2iii1.446 (2)C10—C3vi1.525 (4)
S2—O2iv1.446 (2)C10—H101.0000
S2—O21.446 (2)C10—C111.540 (4)
S2—C21.822 (5)C11—H111.0000
F2—C21.334 (2)C11—C121.532 (4)
C2—F2iv1.334 (2)C11—C131.531 (4)
C2—F2iii1.334 (2)C12—H12A0.9800
Mg1—O3v2.082 (2)C12—H12B0.9800
Mg1—O3vi2.082 (2)C12—H12C0.9800
Mg1—O32.082 (2)C13—H13A0.9800
Mg1—O4vi2.070 (2)C13—H13B0.9800
Mg1—O42.070 (2)C13—H13C0.9800
Mg1—O4v2.070 (2)C14—H14A0.9800
O3—H3A0.944 (13)C14—H14B0.9800
O3—H3B0.953 (13)C14—H14C0.9800
O4—H4A0.962 (13)C15—H151.0000
O4—H4B0.966 (10)C15—C161.529 (4)
O5—C31.351 (3)C15—C171.530 (4)
O5—C41.444 (3)C16—H16A0.9800
O6—C31.197 (3)C16—H16B0.9800
O7—C51.239 (3)C16—H16C0.9800
O8—C71.351 (3)C17—H17A0.9800
O8—C81.454 (3)C17—H17B0.9800
O9—C91.236 (3)C17—H17C0.9800
O10—C71.201 (3)C18—H181.0000
N1—H10.8791C18—C191.531 (4)
N1—C51.326 (4)C18—C201.517 (5)
N1—C61.463 (4)C19—H19A0.9800
N2—H20.8790C19—H19B0.9800
N2—C91.325 (4)C19—H19C0.9800
N2—C101.454 (3)C20—H20A0.9800
C3—C10v1.525 (4)C20—H20B0.9800
C4—H41.0000C20—H20C0.9800
C4—C51.527 (4)
O1i—S1—O1ii115.20 (7)O8—C8—C9110.1 (2)
O1i—S1—O1115.20 (7)O8—C8—C14106.5 (2)
O1ii—S1—O1115.20 (7)C9—C8—H8109.6
O1i—S1—C1102.85 (10)C14—C8—H8109.6
O1ii—S1—C1102.85 (10)C14—C8—C9111.4 (2)
O1—S1—C1102.85 (10)O9—C9—N2123.1 (3)
F1—C1—S1111.3 (2)O9—C9—C8121.3 (3)
F1i—C1—S1111.3 (2)N2—C9—C8115.5 (2)
F1ii—C1—S1111.3 (2)N2—C10—C3vi111.2 (2)
F1i—C1—F1107.6 (2)N2—C10—H10108.8
F1ii—C1—F1107.6 (2)N2—C10—C11109.2 (2)
F1ii—C1—F1i107.6 (2)C3vi—C10—H10108.8
O2iii—S2—O2115.01 (7)C3vi—C10—C11110.1 (2)
O2iv—S2—O2115.01 (7)C11—C10—H10108.8
O2iii—S2—O2iv115.01 (7)C10—C11—H11108.4
O2iii—S2—C2103.11 (9)C12—C11—C10109.7 (2)
O2iv—S2—C2103.11 (9)C12—C11—H11108.4
O2—S2—C2103.11 (9)C13—C11—C10111.6 (2)
F2iv—C2—S2111.01 (19)C13—C11—H11108.4
F2iii—C2—S2111.01 (19)C13—C11—C12110.3 (3)
F2—C2—S2111.01 (19)C11—C12—H12A109.5
F2iii—C2—F2107.9 (2)C11—C12—H12B109.5
F2iii—C2—F2iv107.9 (2)C11—C12—H12C109.5
F2iv—C2—F2107.9 (2)H12A—C12—H12B109.5
O3vi—Mg1—O3v90.60 (10)H12A—C12—H12C109.5
O3v—Mg1—O390.60 (10)H12B—C12—H12C109.5
O3vi—Mg1—O390.60 (10)C11—C13—H13A109.5
O4v—Mg1—O3vi89.78 (9)C11—C13—H13B109.5
O4vi—Mg1—O3v179.61 (11)C11—C13—H13C109.5
O4vi—Mg1—O389.78 (9)H13A—C13—H13B109.5
O4vi—Mg1—O3vi89.46 (10)H13A—C13—H13C109.5
O4v—Mg1—O3179.61 (11)H13B—C13—H13C109.5
O4—Mg1—O3vi179.61 (12)C8—C14—H14A109.5
O4—Mg1—O389.46 (10)C8—C14—H14B109.5
O4v—Mg1—O3v89.46 (10)C8—C14—H14C109.5
O4—Mg1—O3v89.78 (9)H14A—C14—H14B109.5
O4vi—Mg1—O490.15 (11)H14A—C14—H14C109.5
O4v—Mg1—O4vi90.15 (11)H14B—C14—H14C109.5
O4v—Mg1—O490.15 (11)C6—C15—H15108.0
Mg1—O3—H3A119.3 (17)C16—C15—C6110.4 (2)
Mg1—O3—H3B120.1 (17)C16—C15—H15108.0
H3A—O3—H3B112 (2)C16—C15—C17110.1 (2)
Mg1—O4—H4A118 (2)C17—C15—C6112.3 (2)
Mg1—O4—H4B114.4 (18)C17—C15—H15108.0
H4A—O4—H4B109.0 (19)C15—C16—H16A109.5
C3—O5—C4117.5 (2)C15—C16—H16B109.5
C7—O8—C8115.2 (2)C15—C16—H16C109.5
C5—N1—H1119.2H16A—C16—H16B109.5
C5—N1—C6121.4 (2)H16A—C16—H16C109.5
C6—N1—H1119.4H16B—C16—H16C109.5
C9—N2—H2119.3C15—C17—H17A109.5
C9—N2—C10121.4 (2)C15—C17—H17B109.5
C10—N2—H2119.3C15—C17—H17C109.5
O5—C3—C10v109.2 (2)H17A—C17—H17B109.5
O6—C3—O5124.4 (2)H17A—C17—H17C109.5
O6—C3—C10v126.3 (2)H17B—C17—H17C109.5
O5—C4—H4110.0C4—C18—H18107.9
O5—C4—C5110.3 (2)C19—C18—C4110.7 (2)
O5—C4—C18105.6 (2)C19—C18—H18107.9
C5—C4—H4110.0C20—C18—C4111.4 (3)
C5—C4—C18111.0 (2)C20—C18—H18107.9
C18—C4—H4110.0C20—C18—C19110.8 (3)
O7—C5—N1122.1 (3)C18—C19—H19A109.5
O7—C5—C4121.0 (3)C18—C19—H19B109.5
N1—C5—C4116.7 (2)C18—C19—H19C109.5
N1—C6—H6109.3H19A—C19—H19B109.5
N1—C6—C7110.0 (2)H19A—C19—H19C109.5
N1—C6—C15109.1 (2)H19B—C19—H19C109.5
C7—C6—H6109.3C18—C20—H20A109.5
C7—C6—C15109.7 (2)C18—C20—H20B109.5
C15—C6—H6109.3C18—C20—H20C109.5
O8—C7—C6110.4 (2)H20A—C20—H20B109.5
O10—C7—O8124.1 (2)H20A—C20—H20C109.5
O10—C7—C6125.3 (2)H20B—C20—H20C109.5
O8—C8—H8109.6
O1i—S1—C1—F1ii56.91 (15)N2—C10—C11—C13169.9 (2)
O1ii—S1—C1—F1i176.91 (15)C3—O5—C4—C560.6 (3)
O1i—S1—C1—F1176.91 (15)C3—O5—C4—C18179.4 (2)
O1ii—S1—C1—F1ii63.09 (15)C3vi—C10—C11—C12170.1 (2)
O1—S1—C1—F1i56.91 (15)C3vi—C10—C11—C1347.5 (3)
O1—S1—C1—F1ii176.91 (15)C4—O5—C3—O612.8 (4)
O1ii—S1—C1—F156.91 (15)C4—O5—C3—C10v163.1 (2)
O1i—S1—C1—F1i63.09 (15)C5—N1—C6—C759.6 (3)
O1—S1—C1—F163.09 (15)C5—N1—C6—C15180.0 (2)
O2iii—S2—C2—F2iii66.20 (12)C5—C4—C18—C1960.7 (3)
O2iv—S2—C2—F2iv66.20 (13)C5—C4—C18—C20175.4 (3)
O2iv—S2—C2—F253.80 (12)C6—N1—C5—O70.7 (4)
O2iv—S2—C2—F2iii173.80 (12)C6—N1—C5—C4176.3 (2)
O2iii—S2—C2—F2173.80 (12)C7—O8—C8—C962.2 (3)
O2—S2—C2—F2iii53.80 (13)C7—O8—C8—C14176.8 (2)
O2—S2—C2—F266.20 (12)C7—C6—C15—C16168.9 (2)
O2iii—S2—C2—F2iv53.80 (13)C7—C6—C15—C1745.6 (3)
O2—S2—C2—F2iv173.80 (13)C8—O8—C7—O1010.6 (4)
O5—C4—C5—O745.2 (4)C8—O8—C7—C6164.6 (2)
O5—C4—C5—N1139.1 (2)C9—N2—C10—C3vi67.9 (3)
O5—C4—C18—C19179.7 (3)C9—N2—C10—C11170.4 (2)
O5—C4—C18—C2055.9 (3)C10—N2—C9—O96.7 (5)
O8—C8—C9—O938.7 (4)C10—N2—C9—C8177.1 (2)
O8—C8—C9—N2145.1 (2)C14—C8—C9—O979.3 (3)
N1—C6—C7—O8138.5 (2)C14—C8—C9—N297.0 (3)
N1—C6—C7—O1046.4 (4)C15—C6—C7—O8101.5 (2)
N1—C6—C15—C1670.5 (3)C15—C6—C7—O1073.6 (3)
N1—C6—C15—C17166.2 (2)C18—C4—C5—O771.5 (3)
N2—C10—C11—C1267.6 (3)C18—C4—C5—N1104.2 (3)
Symmetry codes: (i) x+y+1, x+1, z; (ii) y+1, xy, z; (iii) x+y+1, x+2, z; (iv) y+2, xy+1, z; (v) x+y, x+1, z; (vi) y+1, xy+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4A···O9v0.96 (1)2.05 (3)2.802 (3)134 (4)
O4—H4B···O70.97 (1)1.74 (1)2.688 (3)167 (3)
O3—H3A···O90.94 (1)1.82 (2)2.717 (3)157 (3)
N1—H1···O10.882.052.933 (4)179
N2—H2···O20.882.052.927 (4)173
Symmetry code: (v) x+y, x+1, z.
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds