Syn and anti conformers of di­ammonium aqua­bis(malonato)oxidovanadate(IV) in an anhydrate crystal

In the anhydrate crystal of di­ammonium aqua­bis­(malonato)oxidovanadate(IV), (NH₄)₂[VO(C₃H₂O₄)₂(H₂O)], two conformers (syn or anti conformation on the equatorial plane) of complex cations are detected. The DFT calculations for the isomers indicate a slight influence of the conformation on their thermodynamic stability. The anionic complexes inter­act with adjacent anions and counter-cations through hydrogen bonds, and the hydrogen bonds lead to a structure with alternate stacking of layers consisting of either anti or syn isomers.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.019
• wR factor = 0.053
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT048_ALERT_1_C MoietyFormula Not Given (or Incomplete) ........     Please Check
PLAT090_ALERT_3_C Poor Data / Parameter Ratio (Zmax > 18) ........       6.99 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         26 Note
PLAT033_ALERT_4_G Flack x Value Deviates > 3.0 * sigma from Zero .      0.270 Note
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          6 Report
PLAT173_ALERT_4_G The CIF-Embedded .res File Contains DANG Records         12 Report
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) V1       --O2        .        7.4 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) V2       --O12       .        5.7 s.u.
PLAT432_ALERT_2_G Short Inter X...Y Contact  O5       ..C6               2.96 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  O15      ..C9               3.01 Ang.
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         32 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT and XPREP (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: XCIF (Bruker, 2014).

Diammonium aquabis(malonato)oxidovanadate(IV)

Crystal data

(NH4)2[V(C3H2O4)2O(H2O)]	Dx = 1.766 Mg m^−3
Mr = 325.13	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 9961 reflections
a = 8.3461 (6) Å	θ = 2.6–28.5°
b = 12.1011 (9) Å	µ = 0.86 mm^−1
c = 24.2118 (17) Å	T = 200 K
V = 2445.3 (3) Å^3	Block, blue
Z = 8	0.15 × 0.13 × 0.12 mm
F(000) = 1336

Data collection

Bruker APEXII CCD area-detector diffractometer	5194 independent reflections
Radiation source: Bruker TXS fine-focus rotating anode	5080 reflections with I > 2σ(I)
Bruker Helios multilayer confocal mirror monochromator	Rint = 0.018
Detector resolution: 8.333 pixels mm^-1	θmax = 26.7°, θmin = 1.7°
φ and ω scans	h = −10→7
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −13→15
	l = −30→29
13364 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.019	w = 1/[σ^2(Fo^2) + (0.0322P)^2 + 0.1094P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.053	(Δ/σ)max = 0.001
S = 1.15	Δρmax = 0.25 e Å^−3
5194 reflections	Δρmin = −0.29 e Å^−3
424 parameters	Absolute structure: Refined as an inversion twin.
32 restraints	Absolute structure parameter: 0.270 (13)

Special details

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

5.8223 (0.0030) x - 0.2546 (0.0072) y + 17.3398 (0.0086) z = 5.6054 (0.0058)

* -0.0205 (0.0008) O3 * 0.0208 (0.0008) O4 * 0.0206 (0.0008) O7 * -0.0209 (0.0008) O8 0.3504 (0.0008) V1

Rms deviation of fitted atoms = 0.0207

0.4684 (0.0044) x - 7.3274 (0.0051) y + 19.2206 (0.0079) z = 6.4071 (0.0078)

Angle to previous plane (with approximate esd) = 51.653 ( 0.044 )

* -0.0056 (0.0007) O13 * 0.0059 (0.0008) O14 * 0.0056 (0.0007) O17 * -0.0058 (0.0008) O18 0.2916 (0.0008) V2

Rms deviation of fitted atoms = 0.0057

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1093 (2)	0.97326 (16)	0.31042 (8)	0.0173 (4)
C2	0.2765 (2)	1.01068 (17)	0.29288 (9)	0.0218 (4)
H2A	0.278377	1.092433	0.291481	0.026*
H2B	0.354366	0.987045	0.321386	0.026*
C3	0.3304 (2)	0.96631 (15)	0.23756 (8)	0.0175 (4)
C4	0.0831 (2)	0.53339 (15)	0.31370 (8)	0.0178 (4)
C5	0.2300 (3)	0.48090 (17)	0.28797 (9)	0.0240 (4)
H5A	0.317370	0.484006	0.315568	0.029*
H5B	0.205558	0.401856	0.281613	0.029*
C6	0.2942 (2)	0.52788 (16)	0.23444 (8)	0.0175 (4)
C7	0.6867 (2)	0.65812 (15)	0.54354 (8)	0.0154 (4)
C8	0.8152 (2)	0.74659 (16)	0.54139 (8)	0.0182 (4)
H8A	0.813831	0.778752	0.503793	0.022*
H8B	0.783289	0.806039	0.567230	0.022*
C9	0.9870 (2)	0.71586 (15)	0.55452 (8)	0.0154 (4)
C10	0.8886 (2)	0.28840 (15)	0.44433 (8)	0.0175 (4)
C11	1.0631 (2)	0.26360 (16)	0.45697 (9)	0.0233 (4)
H11A	1.070206	0.234342	0.495073	0.028*
H11B	1.099936	0.204546	0.431670	0.028*
C12	1.1769 (2)	0.36074 (16)	0.45190 (9)	0.0203 (4)
O1	0.35531 (19)	0.74834 (14)	0.32680 (6)	0.0303 (3)
O2	0.02178 (18)	0.75665 (12)	0.21346 (6)	0.0244 (3)
H2C	0.026 (4)	0.8130 (19)	0.1931 (11)	0.038 (8)*
H2D	0.028 (5)	0.701 (2)	0.1947 (15)	0.080 (13)*
O3	0.07710 (18)	0.87050 (11)	0.30898 (6)	0.0215 (3)
O4	0.32172 (17)	0.86178 (11)	0.22910 (6)	0.0196 (3)
O5	0.01295 (19)	1.04423 (12)	0.32610 (7)	0.0262 (3)
O6	0.38542 (17)	1.03131 (12)	0.20276 (6)	0.0232 (3)
O7	0.06645 (19)	0.63882 (11)	0.31152 (6)	0.0222 (3)
O8	0.30314 (18)	0.63319 (11)	0.22957 (6)	0.0201 (3)
O9	−0.01402 (18)	0.47315 (12)	0.33805 (6)	0.0251 (3)
O10	0.34264 (18)	0.46437 (12)	0.19827 (7)	0.0243 (3)
O11	0.9394 (2)	0.40964 (12)	0.56450 (7)	0.0301 (3)
O12	0.91515 (18)	0.59625 (11)	0.43422 (6)	0.0205 (3)
H12A	0.934 (4)	0.563 (2)	0.4037 (10)	0.046 (9)*
H12B	0.974 (3)	0.6532 (18)	0.4332 (11)	0.031 (7)*
O13	0.71826 (16)	0.55905 (11)	0.52868 (6)	0.0187 (3)
O14	1.03772 (16)	0.61833 (11)	0.54409 (7)	0.0222 (3)
O15	0.55026 (16)	0.68753 (11)	0.55807 (6)	0.0202 (3)
O16	1.07776 (17)	0.78642 (11)	0.57380 (6)	0.0205 (3)
O17	0.82840 (16)	0.38163 (11)	0.45893 (6)	0.0189 (3)
O18	1.14289 (16)	0.45036 (11)	0.47688 (6)	0.0227 (3)
O19	0.80826 (18)	0.21662 (12)	0.42110 (7)	0.0300 (4)
O20	1.30257 (19)	0.34831 (13)	0.42501 (8)	0.0321 (4)
N1	0.5604 (2)	0.49194 (15)	0.41104 (8)	0.0220 (3)
H1A	0.576 (3)	0.490 (2)	0.3747 (8)	0.032 (7)*
H1B	0.478 (3)	0.455 (2)	0.4191 (12)	0.041 (8)*
H1C	0.561 (3)	0.5586 (16)	0.4223 (10)	0.022 (6)*
H1D	0.639 (3)	0.463 (2)	0.4265 (12)	0.041 (8)*
N2	0.7424 (2)	0.74351 (16)	0.32571 (9)	0.0261 (4)
H2E	0.714 (4)	0.739 (2)	0.3587 (9)	0.044 (8)*
H2F	0.717 (4)	0.8101 (18)	0.3140 (11)	0.034 (7)*
H2G	0.844 (3)	0.730 (2)	0.3247 (12)	0.039 (8)*
H2H	0.697 (4)	0.689 (2)	0.3082 (12)	0.045 (9)*
N3	0.4637 (2)	0.73855 (16)	0.14276 (7)	0.0216 (4)
H3A	0.549 (3)	0.753 (2)	0.1276 (11)	0.036 (7)*
H3B	0.386 (3)	0.732 (2)	0.1208 (11)	0.044 (8)*
H3C	0.443 (4)	0.792 (2)	0.1649 (11)	0.042 (8)*
H3D	0.477 (4)	0.678 (2)	0.1577 (14)	0.057 (10)*
N4	0.1713 (2)	0.47891 (16)	0.08469 (8)	0.0219 (4)
H4A	0.097 (3)	0.438 (2)	0.0725 (10)	0.030 (7)*
H4B	0.164 (4)	0.486 (3)	0.1196 (9)	0.055 (10)*
H4C	0.259 (3)	0.450 (2)	0.0776 (12)	0.040 (8)*
H4D	0.162 (4)	0.5452 (19)	0.0741 (12)	0.039 (8)*
V1	0.22054 (4)	0.74995 (3)	0.28043 (2)	0.01603 (8)
V2	0.93035 (4)	0.48827 (2)	0.51199 (2)	0.01528 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0188 (9)	0.0191 (9)	0.0140 (9)	0.0013 (7)	0.0016 (7)	0.0008 (7)
C2	0.0204 (9)	0.0183 (9)	0.0268 (10)	−0.0046 (8)	0.0054 (8)	−0.0056 (8)
C3	0.0125 (7)	0.0168 (9)	0.0232 (10)	0.0006 (7)	0.0016 (7)	−0.0010 (7)
C4	0.0201 (9)	0.0174 (9)	0.0157 (9)	−0.0015 (7)	0.0002 (8)	−0.0007 (7)
C5	0.0244 (9)	0.0180 (9)	0.0296 (11)	0.0034 (8)	0.0073 (8)	0.0080 (8)
C6	0.0134 (8)	0.0167 (8)	0.0225 (10)	0.0015 (7)	0.0003 (7)	0.0012 (7)
C7	0.0152 (8)	0.0183 (8)	0.0128 (9)	0.0002 (7)	−0.0019 (7)	0.0019 (7)
C8	0.0147 (8)	0.0146 (8)	0.0255 (9)	0.0005 (7)	−0.0005 (7)	−0.0005 (8)
C9	0.0154 (8)	0.0185 (9)	0.0123 (9)	−0.0016 (7)	0.0006 (7)	0.0009 (7)
C10	0.0169 (9)	0.0157 (8)	0.0199 (10)	−0.0006 (7)	0.0007 (7)	−0.0003 (7)
C11	0.0165 (9)	0.0166 (9)	0.0369 (11)	0.0020 (8)	−0.0010 (8)	−0.0021 (8)
C12	0.0148 (9)	0.0186 (9)	0.0274 (11)	0.0016 (7)	−0.0009 (8)	−0.0022 (8)
O1	0.0312 (8)	0.0327 (8)	0.0268 (8)	0.0009 (7)	−0.0055 (6)	0.0020 (8)
O2	0.0320 (8)	0.0141 (7)	0.0273 (7)	0.0011 (6)	−0.0044 (6)	−0.0012 (6)
O3	0.0205 (7)	0.0180 (6)	0.0260 (8)	−0.0008 (6)	0.0079 (6)	−0.0024 (5)
O4	0.0231 (7)	0.0151 (6)	0.0207 (8)	−0.0029 (5)	0.0061 (6)	−0.0012 (5)
O5	0.0258 (7)	0.0197 (7)	0.0333 (9)	0.0047 (6)	0.0106 (6)	0.0028 (6)
O6	0.0244 (7)	0.0180 (7)	0.0272 (8)	−0.0030 (6)	0.0048 (6)	0.0033 (6)
O7	0.0242 (7)	0.0162 (6)	0.0263 (8)	0.0007 (6)	0.0094 (6)	0.0014 (5)
O8	0.0233 (7)	0.0152 (6)	0.0217 (8)	0.0013 (5)	0.0070 (6)	0.0013 (5)
O9	0.0283 (7)	0.0196 (7)	0.0272 (8)	−0.0057 (6)	0.0104 (6)	−0.0004 (6)
O10	0.0243 (7)	0.0208 (7)	0.0279 (8)	0.0039 (6)	0.0029 (6)	−0.0047 (6)
O11	0.0403 (9)	0.0234 (7)	0.0267 (8)	0.0059 (7)	−0.0047 (7)	0.0058 (6)
O12	0.0235 (7)	0.0164 (7)	0.0217 (8)	−0.0007 (6)	0.0036 (6)	−0.0007 (5)
O13	0.0159 (6)	0.0162 (6)	0.0240 (7)	−0.0005 (5)	0.0014 (5)	−0.0015 (5)
O14	0.0163 (7)	0.0183 (6)	0.0320 (8)	0.0022 (5)	−0.0069 (6)	−0.0066 (6)
O15	0.0155 (6)	0.0202 (6)	0.0248 (7)	0.0019 (6)	0.0032 (6)	0.0000 (5)
O16	0.0199 (6)	0.0188 (6)	0.0227 (7)	−0.0042 (6)	−0.0030 (6)	−0.0031 (5)
O17	0.0150 (6)	0.0155 (6)	0.0261 (8)	0.0005 (5)	−0.0015 (6)	−0.0023 (5)
O18	0.0151 (6)	0.0182 (7)	0.0347 (9)	0.0003 (5)	0.0003 (6)	−0.0062 (6)
O19	0.0230 (7)	0.0201 (7)	0.0468 (10)	0.0003 (6)	−0.0077 (7)	−0.0126 (7)
O20	0.0192 (7)	0.0267 (8)	0.0504 (11)	−0.0009 (6)	0.0117 (7)	−0.0093 (7)
N1	0.0209 (8)	0.0189 (8)	0.0262 (10)	−0.0001 (8)	−0.0030 (7)	−0.0015 (7)
N2	0.0274 (9)	0.0205 (9)	0.0304 (10)	−0.0005 (8)	0.0079 (8)	0.0002 (8)
N3	0.0238 (9)	0.0205 (9)	0.0206 (9)	0.0007 (7)	0.0053 (7)	−0.0004 (7)
N4	0.0195 (8)	0.0196 (9)	0.0264 (10)	−0.0006 (7)	0.0040 (7)	−0.0006 (7)
V1	0.01743 (15)	0.01364 (15)	0.01701 (16)	−0.00016 (12)	0.00290 (11)	0.00055 (13)
V2	0.01464 (14)	0.01294 (14)	0.01825 (16)	0.00112 (12)	−0.00192 (12)	−0.00076 (12)

Geometric parameters (Å, º)

C1—O5	1.236 (2)	O1—V1	1.5892 (15)
C1—O3	1.273 (2)	O2—V1	2.3211 (15)
C1—C2	1.527 (3)	O2—H2C	0.84 (2)
C2—C3	1.511 (3)	O2—H2D	0.82 (2)
C2—H2A	0.9900	O3—V1	2.0097 (14)
C2—H2B	0.9900	O4—V1	2.0223 (14)
C3—O6	1.241 (2)	O7—V1	2.0072 (14)
C3—O4	1.283 (2)	O8—V1	1.9970 (14)
C4—O9	1.239 (2)	O11—V2	1.5899 (15)
C4—O7	1.284 (2)	O12—V2	2.2954 (15)
C4—C5	1.514 (3)	O12—H12A	0.85 (2)
C5—C6	1.513 (3)	O12—H12B	0.84 (2)
C5—H5A	0.9900	O13—V2	2.0076 (14)
C5—H5B	0.9900	O14—V2	1.9708 (14)
C6—O10	1.233 (2)	O17—V2	2.0098 (14)
C6—O8	1.282 (2)	O18—V2	2.0198 (14)
C7—O15	1.244 (2)	N1—H1A	0.891 (19)
C7—O13	1.279 (2)	N1—H1B	0.84 (2)
C7—C8	1.517 (3)	N1—H1C	0.851 (19)
C8—C9	1.515 (2)	N1—H1D	0.83 (2)
C8—H8A	0.9900	N2—H2E	0.83 (2)
C8—H8B	0.9900	N2—H2F	0.88 (2)
C9—O16	1.233 (2)	N2—H2G	0.86 (2)
C9—O14	1.279 (2)	N2—H2H	0.87 (2)
C10—O19	1.233 (2)	N3—H3A	0.82 (2)
C10—O17	1.284 (2)	N3—H3B	0.84 (2)
C10—C11	1.519 (3)	N3—H3C	0.85 (2)
C11—C12	1.516 (3)	N3—H3D	0.83 (2)
C11—H11A	0.9900	N4—H4A	0.85 (2)
C11—H11B	0.9900	N4—H4B	0.85 (2)
C12—O20	1.244 (3)	N4—H4C	0.83 (2)
C12—O18	1.274 (2)	N4—H4D	0.85 (2)
O5—C1—O3	123.34 (18)	C7—O13—V2	129.64 (12)
O5—C1—C2	118.28 (18)	C9—O14—V2	131.62 (12)
O3—C1—C2	118.37 (17)	C10—O17—V2	125.06 (13)
C3—C2—C1	114.38 (16)	C12—O18—V2	126.06 (13)
C3—C2—H2A	108.7	H1A—N1—H1B	110 (3)
C1—C2—H2A	108.7	H1A—N1—H1C	110 (2)
C3—C2—H2B	108.7	H1B—N1—H1C	116 (3)
C1—C2—H2B	108.7	H1A—N1—H1D	109 (3)
H2A—C2—H2B	107.6	H1B—N1—H1D	108 (3)
O6—C3—O4	122.49 (19)	H1C—N1—H1D	105 (3)
O6—C3—C2	119.12 (17)	H2E—N2—H2F	108 (3)
O4—C3—C2	118.35 (17)	H2E—N2—H2G	107 (3)
O9—C4—O7	122.19 (19)	H2F—N2—H2G	114 (3)
O9—C4—C5	118.58 (17)	H2E—N2—H2H	107 (3)
O7—C4—C5	119.17 (17)	H2F—N2—H2H	116 (3)
C6—C5—C4	118.78 (16)	H2G—N2—H2H	106 (3)
C6—C5—H5A	107.6	H3A—N3—H3B	114 (2)
C4—C5—H5A	107.6	H3A—N3—H3C	107 (3)
C6—C5—H5B	107.6	H3B—N3—H3C	108 (3)
C4—C5—H5B	107.6	H3A—N3—H3D	105 (3)
H5A—C5—H5B	107.1	H3B—N3—H3D	107 (3)
O10—C6—O8	122.34 (18)	H3C—N3—H3D	115 (3)
O10—C6—C5	119.35 (17)	H4A—N4—H4B	111 (3)
O8—C6—C5	118.22 (17)	H4A—N4—H4C	109 (3)
O15—C7—O13	122.43 (17)	H4B—N4—H4C	108 (3)
O15—C7—C8	117.08 (16)	H4A—N4—H4D	112 (3)
O13—C7—C8	120.42 (16)	H4B—N4—H4D	101 (3)
C9—C8—C7	119.27 (16)	H4C—N4—H4D	115 (3)
C9—C8—H8A	107.5	O1—V1—O8	100.52 (8)
C7—C8—H8A	107.5	O1—V1—O7	100.39 (8)
C9—C8—H8B	107.5	O8—V1—O7	88.76 (6)
C7—C8—H8B	107.5	O1—V1—O3	100.81 (8)
H8A—C8—H8B	107.0	O8—V1—O3	158.63 (6)
O16—C9—O14	120.68 (17)	O7—V1—O3	88.61 (6)
O16—C9—C8	119.39 (17)	O1—V1—O4	98.44 (7)
O14—C9—C8	119.90 (16)	O8—V1—O4	87.15 (5)
O19—C10—O17	122.13 (18)	O7—V1—O4	161.16 (6)
O19—C10—C11	118.31 (17)	O3—V1—O4	88.53 (6)
O17—C10—C11	119.54 (17)	O1—V1—O2	178.57 (7)
C12—C11—C10	115.54 (16)	O8—V1—O2	80.83 (6)
C12—C11—H11A	108.4	O7—V1—O2	80.07 (6)
C10—C11—H11A	108.4	O3—V1—O2	77.83 (6)
C12—C11—H11B	108.4	O4—V1—O2	81.12 (6)
C10—C11—H11B	108.4	O11—V2—O14	98.10 (8)
H11A—C11—H11B	107.5	O11—V2—O13	97.84 (8)
O20—C12—O18	122.63 (18)	O14—V2—O13	88.90 (6)
O20—C12—C11	118.47 (17)	O11—V2—O17	98.45 (7)
O18—C12—C11	118.85 (18)	O14—V2—O17	163.20 (6)
V1—O2—H2C	114 (2)	O13—V2—O17	91.68 (6)
V1—O2—H2D	108 (3)	O11—V2—O18	99.14 (8)
H2C—O2—H2D	110 (3)	O14—V2—O18	87.02 (6)
C1—O3—V1	126.35 (13)	O13—V2—O18	162.94 (6)
C3—O4—V1	125.80 (13)	O17—V2—O18	87.54 (6)
C4—O7—V1	127.70 (14)	O11—V2—O12	177.91 (7)
C6—O8—V1	128.79 (13)	O14—V2—O12	83.92 (6)
V2—O12—H12A	116 (2)	O13—V2—O12	82.74 (6)
V2—O12—H12B	117.2 (19)	O17—V2—O12	79.51 (6)
H12A—O12—H12B	104 (3)	O18—V2—O12	80.36 (6)
O5—C1—C2—C3	−130.1 (2)	O5—C1—O3—V1	176.46 (15)
O3—C1—C2—C3	51.0 (3)	C2—C1—O3—V1	−4.7 (3)
C1—C2—C3—O6	130.24 (19)	O6—C3—O4—V1	−175.44 (14)
C1—C2—C3—O4	−51.8 (2)	C2—C3—O4—V1	6.7 (2)
O9—C4—C5—C6	144.90 (19)	O9—C4—O7—V1	173.81 (15)
O7—C4—C5—C6	−37.8 (3)	C5—C4—O7—V1	−3.4 (3)
C4—C5—C6—O10	−139.71 (19)	O10—C6—O8—V1	175.81 (14)
C4—C5—C6—O8	43.6 (3)	C5—C6—O8—V1	−7.6 (3)
O15—C7—C8—C9	147.45 (18)	O15—C7—O13—V2	−172.31 (14)
O13—C7—C8—C9	−35.4 (3)	C8—C7—O13—V2	10.7 (3)
C7—C8—C9—O16	−151.89 (18)	O16—C9—O14—V2	−178.19 (13)
C7—C8—C9—O14	30.1 (3)	C8—C9—O14—V2	−0.2 (3)
O19—C10—C11—C12	144.3 (2)	O19—C10—O17—V2	164.68 (16)
O17—C10—C11—C12	−37.0 (3)	C11—C10—O17—V2	−13.9 (3)
C10—C11—C12—O20	−131.2 (2)	O20—C12—O18—V2	170.31 (16)
C10—C11—C12—O18	51.3 (3)	C11—C12—O18—V2	−12.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2C···O9^i	0.84 (2)	2.08 (2)	2.902 (2)	165 (3)
O2—H2D···O5^ii	0.82 (2)	1.99 (3)	2.758 (2)	157 (4)
O12—H12A···O9^iii	0.85 (2)	1.98 (2)	2.826 (2)	174 (3)
O12—H12B···O15^iv	0.84 (2)	2.04 (2)	2.855 (2)	161 (3)
N1—H1A···O6^v	0.89 (2)	1.97 (2)	2.833 (2)	164 (2)
N1—H1B···O20^vi	0.84 (2)	1.96 (2)	2.787 (2)	168 (3)
N1—H1C···O16^vii	0.85 (2)	1.88 (2)	2.711 (2)	164 (2)
N1—H1D···O17	0.83 (2)	2.02 (2)	2.851 (2)	175 (3)
N2—H2E···O16^vii	0.83 (2)	2.01 (2)	2.818 (2)	161 (3)
N2—H2F···O10^viii	0.88 (2)	1.96 (2)	2.826 (3)	170 (3)
N2—H2G···O7^iii	0.86 (2)	2.18 (2)	3.006 (2)	159 (3)
N2—H2H···O6^v	0.87 (2)	2.04 (2)	2.865 (2)	156 (3)
N3—H3A···O20^ix	0.82 (2)	2.12 (2)	2.874 (2)	153 (3)
N3—H3B···O19^viii	0.84 (2)	1.92 (2)	2.759 (2)	173 (3)
N3—H3C···O4	0.85 (2)	2.04 (2)	2.828 (2)	153 (3)
N3—H3D···O8	0.83 (2)	2.33 (3)	2.800 (2)	116 (3)
N4—H4A···O15^x	0.85 (2)	1.98 (2)	2.809 (2)	164 (3)
N4—H4B···O5^ii	0.85 (2)	2.10 (3)	2.767 (2)	135 (3)
N4—H4B···O10	0.85 (2)	2.43 (3)	3.105 (2)	136 (3)
N4—H4C···O14^xi	0.83 (2)	2.05 (2)	2.872 (2)	169 (3)
N4—H4D···O19^viii	0.85 (2)	2.09 (2)	2.885 (2)	156 (3)
C2—H2B···O10^viii	0.99	2.59	3.235 (3)	123
C5—H5A···O6^v	0.99	2.58	3.275 (3)	127
C5—H5B···O2^ii	0.99	2.59	3.432 (3)	143
C8—H8A···O15^iv	0.99	2.51	3.207 (2)	127

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x, y−1/2, −z+1/2; (iii) x+1, y, z; (iv) x+1/2, −y+3/2, −z+1; (v) −x+1, y−1/2, −z+1/2; (vi) x−1, y, z; (vii) x−1/2, −y+3/2, −z+1; (viii) −x+1, y+1/2, −z+1/2; (ix) −x+2, y+1/2, −z+1/2; (x) −x+1/2, −y+1, z−1/2; (xi) −x+3/2, −y+1, z−1/2.