Tetra­ammonium bis­(metforminium) di-μ₆-oxido-tetra-μ₃-oxido-tetra­deca-μ₂-oxido-octa­oxidodeca­vanadium(V) hexa­hydrate

The title compound, (NH₄)₄(C₄H₁₂N₅)₂[V₁₀O₂₈]·6H₂O, crystallizes with the deca­vanadate anion placed on an inversion centre in space group P. This anion is surrounded by a first shell of ammonium cations and water mol­ecules, forming efficient N—H...O and O—H...O hydrogen bonds. A second shell includes metforminium monocations with a twisted geometry, also forming numerous inter­molecular hydrogen bonds. The complex three-dimensional network of non-covalent inter­actions affords a crystal structure in which the cations and anions are densely packed.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](N-C) = 0.002 Å
• R factor = 0.025
• wR factor = 0.078
• Data-to-parameter ratio = 31.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.3 Note
PLAT352_ALERT_3_C Short  N-H (X0.87,N1.01A)  N1       - H1B      .       0.76 Ang.
PLAT352_ALERT_3_C Short  N-H (X0.87,N1.01A)  N4       - H4E      .       0.74 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D       H15B     ..H16A     .       2.12 Ang.
                                                    1+x,y,z  =      1_655 Check
PLAT420_ALERT_2_C D-H Bond Without Acceptor  N1       --H1B      .     Please Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1B      ..O6       .       2.71 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.033 Report
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          6 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          8 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          9 Note
PLAT019_ALERT_1_G _diffrn_measured_fraction_theta_full/*_max < 1.0      0.997 Report
PLAT042_ALERT_1_G Calc. and Reported Moiety Formula Strings Differ     Please Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  V1       --O7       .        8.0 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  V1       --O8       .        6.7 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  V1       --O14_a    .        8.0 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  V2       --O2       .        5.0 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  V2       --O14_a    .        7.0 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  V3       --O3       .        6.3 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  V3       --O14      .       10.0 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  V3       --O14_a    .       13.0 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  V4       --O11      .        5.3 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  V4       --O14_a    .        7.0 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  V5       --O5       .        5.5 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  V5       --O14_a    .       12.0 s.u.
PLAT432_ALERT_2_G Short Inter X...Y Contact  O1       ..C4               2.99 Ang.
                                                 1-x,2-y,-z  =      2_675 Check
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       1.18 Ratio
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          6 Note
              H4 N
PLAT794_ALERT_5_G Tentative Bond Valency for V1        (V)       .       5.02 Info
PLAT794_ALERT_5_G Tentative Bond Valency for V2        (V)       .       5.04 Info
PLAT794_ALERT_5_G Tentative Bond Valency for V3        (V)       .       5.02 Info
PLAT794_ALERT_5_G Tentative Bond Valency for V4        (V)       .       5.05 Info
PLAT794_ALERT_5_G Tentative Bond Valency for V5        (V)       .       4.97 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          9 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          7 Note
PLAT982_ALERT_1_G The  V-f'=    0.2316 Deviates from  IT-value =       0.2276 Check
PLAT983_ALERT_1_G The  V-f"=    0.3398 Deviates from  IT-Value =       0.3376 Check

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

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

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2020); cell refinement: X-AREA (Stoe & Cie, 2020); data reduction: X-AREA (Stoe & Cie, 2020); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

Tetraammonium bis(metforminium) di-µ₆-oxido-tetra-µ₃-oxido-tetradeca-µ₂-oxido-octaoxidodecavanadium(V) hexahydrate

Crystal data

(NH4)4(C4H12N5)2[V10O28]·6H2O	Z = 1
Mr = 1398.03	F(000) = 700
Triclinic, P1	Dx = 2.121 Mg m^−3
a = 9.7965 (2) Å	Ag Kα radiation, λ = 0.56083 Å
b = 10.1010 (2) Å	Cell parameters from 131899 reflections
c = 13.0974 (3) Å	θ = 2.2–33.7°
α = 81.081 (2)°	µ = 1.10 mm^−1
β = 70.906 (2)°	T = 295 K
γ = 63.321 (2)°	Tetrahedron, gold
V = 1094.30 (5) Å^3	0.26 × 0.26 × 0.19 mm

Data collection

Stoe Stadivari diffractometer	11269 independent reflections
Radiation source: Sealed X-ray tube, Axo Astix-f Microfocus source	9224 reflections with I > 2σ(I)
Graded multilayer mirror monochromator	Rint = 0.030
Detector resolution: 5.81 pixels mm^-1	θmax = 28.5°, θmin = 2.2°
ω scans	h = −16→16
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2020)	k = −17→17
Tmin = 0.426, Tmax = 0.907	l = −22→21
94693 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.078	w = 1/[σ^2(Fo^2) + (0.0487P)^2 + 0.0305P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.002
11269 reflections	Δρmax = 0.47 e Å^−3
361 parameters	Δρmin = −0.95 e Å^−3
9 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.0048 (9)
Primary atom site location: dual

Special details

Refinement. All H atoms, with exception of the methyl groups in the HMetf⁺ cation, were refined with free coordinates and isotropic displacement parameters calculated as U_iso(H) = 1.2 or 1.5×U_eq(carrier atom). The geometry for the three water molecules was restrained, with target bond lengths O—H = 0.85 (2) Å and H···H separations of 1.34 (2) Å. Methyl H atoms were included using a riding model with U_iso(H) = 1.5×U_eq(carrier atom).

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

	x	y	z	Uiso*/Ueq
V1	0.39655 (2)	0.84689 (2)	0.38300 (2)	0.02229 (4)
V2	0.22257 (2)	0.64431 (2)	0.44890 (2)	0.02011 (3)
V3	0.44412 (2)	0.63696 (2)	0.58069 (2)	0.01697 (3)
V4	0.72567 (2)	0.57810 (2)	0.36227 (2)	0.01973 (3)
V5	0.50248 (2)	0.59053 (2)	0.23433 (2)	0.02221 (4)
O1	0.33595 (10)	1.02437 (8)	0.37493 (7)	0.03200 (16)
O2	0.04039 (9)	0.66456 (10)	0.48094 (7)	0.02993 (15)
O3	0.43043 (9)	0.62643 (8)	0.71288 (5)	0.02402 (13)
O4	0.90793 (9)	0.55609 (9)	0.33301 (7)	0.02955 (15)
O5	0.52329 (11)	0.57067 (11)	0.11007 (6)	0.03517 (18)
O6	0.20204 (8)	0.83200 (8)	0.43086 (6)	0.02483 (13)
O7	0.38555 (9)	0.81825 (7)	0.54386 (6)	0.02400 (13)
O8	0.61636 (8)	0.77845 (7)	0.36354 (6)	0.02343 (12)
O9	0.43593 (9)	0.79045 (8)	0.24684 (6)	0.02459 (13)
O10	0.24430 (7)	0.63107 (7)	0.59608 (5)	0.01873 (11)
O11	0.66939 (8)	0.57599 (7)	0.52504 (5)	0.01927 (11)
O12	0.71111 (8)	0.55367 (8)	0.23235 (5)	0.02325 (12)
O13	0.29624 (8)	0.60661 (8)	0.30286 (5)	0.02357 (12)
O14	0.52088 (7)	0.40515 (7)	0.58287 (5)	0.01779 (10)
C1	0.06586 (13)	1.15154 (12)	0.16742 (9)	0.03002 (19)
C2	0.26523 (13)	1.04792 (11)	0.00500 (8)	0.02878 (18)
C3	0.2491 (2)	0.8359 (2)	−0.04832 (12)	0.0567 (5)
H3A	0.301998	0.759308	−0.002811	0.085*
H3B	0.268909	0.794033	−0.115518	0.085*
H3C	0.136312	0.880514	−0.012978	0.085*
C4	0.42436 (17)	0.94509 (16)	−0.17351 (10)	0.0408 (3)
H4A	0.377248	1.032108	−0.214239	0.061*
H4B	0.453653	0.858445	−0.212180	0.061*
H4C	0.517801	0.943143	−0.163104	0.061*
N1	0.02667 (15)	1.12792 (15)	0.27388 (9)	0.0428 (3)
H1A	−0.050 (2)	1.197 (2)	0.3093 (15)	0.051*
H1B	0.078 (2)	1.055 (2)	0.2967 (16)	0.051*
N2	−0.00914 (13)	1.28620 (12)	0.13003 (9)	0.0373 (2)
H2A	−0.089 (2)	1.355 (2)	0.1705 (14)	0.045*
H2B	0.000 (2)	1.299 (2)	0.0630 (15)	0.045*
N3	0.17233 (12)	1.03435 (10)	0.10395 (7)	0.03244 (19)
N4	0.32345 (14)	1.14908 (13)	−0.02036 (10)	0.0388 (2)
H4D	0.381 (2)	1.154 (2)	−0.0901 (15)	0.047*
H4E	0.301 (2)	1.201 (2)	0.0224 (15)	0.047*
N5	0.30971 (13)	0.94745 (11)	−0.06891 (7)	0.03350 (19)
N6	0.18645 (12)	1.10848 (11)	0.61533 (8)	0.02925 (17)
H6A	0.252 (2)	1.143 (2)	0.6196 (14)	0.044*
H6B	0.110 (2)	1.130 (2)	0.6764 (15)	0.044*
H6C	0.238 (2)	1.022 (2)	0.5989 (14)	0.044*
H6D	0.143 (2)	1.156 (2)	0.5644 (15)	0.044*
N7	0.22214 (11)	0.34134 (10)	0.33362 (8)	0.02681 (15)
H7A	0.258 (2)	0.3611 (19)	0.2689 (15)	0.040*
H7B	0.117 (2)	0.3902 (19)	0.3535 (13)	0.040*
H7C	0.247 (2)	0.250 (2)	0.3412 (14)	0.040*
H7D	0.265 (2)	0.3602 (19)	0.3754 (14)	0.040*
O15	0.99461 (17)	0.64089 (15)	0.09649 (9)	0.0543 (3)
H15A	0.924 (2)	0.621 (3)	0.1371 (18)	0.081*
H15B	1.021 (3)	0.683 (3)	0.1260 (19)	0.081*
O16	0.28519 (14)	0.39198 (12)	0.10371 (8)	0.0451 (2)
H16A	0.204 (2)	0.464 (2)	0.1036 (18)	0.068*
H16B	0.365 (2)	0.405 (2)	0.0658 (17)	0.068*
O17	0.07918 (11)	0.80032 (11)	0.20277 (7)	0.03818 (19)
H17A	0.152 (2)	0.7348 (19)	0.2284 (15)	0.057*
H17B	0.114 (2)	0.8621 (19)	0.1780 (16)	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
V1	0.02379 (7)	0.01451 (6)	0.02375 (7)	−0.00547 (5)	−0.00600 (5)	0.00227 (4)
V2	0.01597 (6)	0.02161 (7)	0.02045 (6)	−0.00631 (5)	−0.00604 (5)	0.00221 (5)
V3	0.01774 (6)	0.01375 (6)	0.01733 (6)	−0.00493 (4)	−0.00428 (4)	−0.00203 (4)
V4	0.01655 (6)	0.01890 (6)	0.02113 (6)	−0.00737 (5)	−0.00352 (5)	0.00193 (4)
V5	0.02394 (7)	0.02343 (7)	0.01623 (6)	−0.00812 (5)	−0.00540 (5)	0.00068 (5)
O1	0.0359 (4)	0.0162 (3)	0.0350 (4)	−0.0073 (3)	−0.0061 (3)	0.0027 (2)
O2	0.0196 (3)	0.0363 (4)	0.0325 (4)	−0.0114 (3)	−0.0096 (3)	0.0059 (3)
O3	0.0284 (3)	0.0222 (3)	0.0195 (3)	−0.0088 (2)	−0.0060 (2)	−0.0034 (2)
O4	0.0198 (3)	0.0333 (4)	0.0332 (4)	−0.0122 (3)	−0.0063 (3)	0.0058 (3)
O5	0.0416 (4)	0.0430 (5)	0.0189 (3)	−0.0167 (4)	−0.0084 (3)	−0.0002 (3)
O6	0.0202 (3)	0.0191 (3)	0.0278 (3)	−0.0038 (2)	−0.0057 (2)	0.0022 (2)
O7	0.0275 (3)	0.0148 (3)	0.0256 (3)	−0.0063 (2)	−0.0059 (2)	−0.0018 (2)
O8	0.0232 (3)	0.0187 (3)	0.0275 (3)	−0.0099 (2)	−0.0063 (2)	0.0027 (2)
O9	0.0254 (3)	0.0218 (3)	0.0227 (3)	−0.0078 (2)	−0.0077 (2)	0.0043 (2)
O10	0.0164 (2)	0.0165 (2)	0.0186 (2)	−0.00421 (19)	−0.00313 (19)	−0.00076 (18)
O11	0.0192 (3)	0.0188 (3)	0.0201 (3)	−0.0082 (2)	−0.0060 (2)	−0.00041 (19)
O12	0.0210 (3)	0.0247 (3)	0.0184 (3)	−0.0073 (2)	−0.0024 (2)	−0.0001 (2)
O13	0.0234 (3)	0.0266 (3)	0.0214 (3)	−0.0103 (2)	−0.0088 (2)	0.0018 (2)
O14	0.0169 (2)	0.0156 (2)	0.0186 (2)	−0.0056 (2)	−0.00443 (19)	−0.00012 (18)
C1	0.0266 (4)	0.0305 (5)	0.0278 (4)	−0.0078 (4)	−0.0042 (3)	−0.0085 (3)
C2	0.0271 (4)	0.0238 (4)	0.0266 (4)	−0.0051 (3)	−0.0037 (3)	−0.0035 (3)
C3	0.0736 (11)	0.0555 (9)	0.0407 (7)	−0.0432 (8)	0.0149 (7)	−0.0195 (6)
C4	0.0440 (6)	0.0412 (6)	0.0261 (5)	−0.0177 (5)	0.0048 (4)	−0.0050 (4)
N1	0.0390 (5)	0.0437 (6)	0.0251 (4)	−0.0017 (5)	−0.0030 (4)	−0.0092 (4)
N2	0.0353 (5)	0.0281 (4)	0.0343 (5)	−0.0034 (4)	−0.0039 (4)	−0.0079 (3)
N3	0.0342 (4)	0.0260 (4)	0.0234 (4)	−0.0058 (3)	0.0004 (3)	−0.0048 (3)
N4	0.0403 (5)	0.0346 (5)	0.0367 (5)	−0.0174 (4)	0.0002 (4)	−0.0080 (4)
N5	0.0390 (5)	0.0300 (4)	0.0237 (4)	−0.0148 (4)	0.0032 (3)	−0.0059 (3)
N6	0.0284 (4)	0.0227 (4)	0.0323 (4)	−0.0077 (3)	−0.0070 (3)	−0.0029 (3)
N7	0.0254 (4)	0.0237 (4)	0.0315 (4)	−0.0102 (3)	−0.0087 (3)	−0.0008 (3)
O15	0.0633 (7)	0.0591 (7)	0.0337 (5)	−0.0251 (6)	−0.0099 (5)	0.0053 (4)
O16	0.0503 (6)	0.0430 (5)	0.0348 (4)	−0.0206 (4)	−0.0042 (4)	0.0031 (4)
O17	0.0328 (4)	0.0406 (5)	0.0318 (4)	−0.0107 (4)	−0.0091 (3)	0.0082 (3)

Geometric parameters (Å, º)

V1—O1	1.6137 (7)	V5—O14^i	2.3350 (6)
V1—O9	1.8226 (7)	C1—N2	1.3271 (16)
V1—O6	1.8689 (8)	C1—N1	1.3332 (15)
V1—O8	1.8811 (7)	C1—N3	1.3451 (13)
V1—O7	2.0554 (7)	C2—N4	1.3318 (16)
V1—O14^i	2.3173 (6)	C2—N5	1.3374 (13)
V1—V5	3.0663 (2)	C2—N3	1.3460 (14)
V1—V2	3.0755 (2)	C3—N5	1.4474 (18)
V1—V3	3.1011 (2)	C3—H3A	0.9600
V1—V4	3.1042 (2)	C3—H3B	0.9600
V2—O2	1.6161 (8)	C3—H3C	0.9600
V2—O6	1.8001 (7)	C4—N5	1.4554 (14)
V2—O13	1.8440 (7)	C4—H4A	0.9600
V2—O10	1.9854 (7)	C4—H4B	0.9600
V2—O11^i	2.0185 (7)	C4—H4C	0.9600
V2—O14^i	2.2343 (6)	N1—H1A	0.818 (19)
V2—V4^i	3.0815 (2)	N1—H1B	0.76 (2)
V3—O3	1.6825 (7)	N2—H2A	0.854 (18)
V3—O7	1.6968 (7)	N2—H2B	0.849 (19)
V3—O11	1.9098 (7)	N4—H4D	0.912 (19)
V3—O10	1.9284 (7)	N4—H4E	0.736 (19)
V3—O14	2.1121 (6)	N6—H6A	0.882 (19)
V3—O14^i	2.1349 (6)	N6—H6B	0.874 (18)
V3—V5^i	3.0737 (2)	N6—H6C	0.808 (19)
V4—O4	1.6145 (7)	N6—H6D	0.873 (19)
V4—O8	1.8153 (7)	N7—H7A	0.835 (18)
V4—O12	1.8158 (7)	N7—H7B	0.880 (18)
V4—O10^i	2.0094 (7)	N7—H7C	0.843 (19)
V4—O11	2.0192 (6)	N7—H7D	0.873 (18)
V4—O14^i	2.2168 (6)	O15—H15A	0.812 (16)
V4—V5	3.1128 (2)	O15—H15B	0.778 (16)
V5—O5	1.6055 (8)	O16—H16A	0.804 (15)
V5—O9	1.8385 (7)	O16—H16B	0.830 (15)
V5—O13	1.8649 (7)	O17—H17A	0.850 (14)
V5—O12	1.8978 (7)	O17—H17B	0.820 (15)
V5—O3^i	2.0607 (7)
O1—V1—O9	104.84 (4)	O12—V4—V1	84.23 (2)
O1—V1—O6	101.04 (4)	O10^i—V4—V1	124.447 (19)
O9—V1—O6	92.16 (3)	O11—V4—V1	87.655 (19)
O1—V1—O8	102.51 (4)	O14^i—V4—V1	48.162 (16)
O9—V1—O8	91.10 (3)	V2^i—V4—V1	120.184 (6)
O6—V1—O8	154.52 (3)	O4—V4—V5	136.16 (3)
O1—V1—O7	98.71 (4)	O8—V4—V5	84.21 (2)
O9—V1—O7	156.44 (3)	O12—V4—V5	33.88 (2)
O6—V1—O7	83.85 (3)	O10^i—V4—V5	87.47 (2)
O8—V1—O7	83.12 (3)	O11—V4—V5	124.45 (2)
O1—V1—O14^i	172.87 (4)	O14^i—V4—V5	48.462 (16)
O9—V1—O14^i	82.28 (3)	V2^i—V4—V5	119.451 (6)
O6—V1—O14^i	78.35 (3)	V1—V4—V5	59.105 (6)
O8—V1—O14^i	77.07 (3)	O5—V5—O9	104.08 (4)
O7—V1—O14^i	74.17 (2)	O5—V5—O13	102.38 (4)
O1—V1—V5	138.11 (3)	O9—V5—O13	91.70 (3)
O9—V1—V5	33.28 (2)	O5—V5—O12	102.89 (4)
O6—V1—V5	84.42 (2)	O9—V5—O12	90.47 (3)
O8—V1—V5	84.55 (2)	O13—V5—O12	153.29 (3)
O7—V1—V5	123.18 (2)	O5—V5—O3^i	100.16 (4)
O14^i—V1—V5	49.017 (16)	O9—V5—O3^i	155.75 (3)
O1—V1—V2	133.39 (3)	O13—V5—O3^i	83.71 (3)
O9—V1—V2	83.40 (3)	O12—V5—O3^i	83.45 (3)
O6—V1—V2	32.35 (2)	O5—V5—O14^i	174.46 (4)
O8—V1—V2	123.42 (2)	O9—V5—O14^i	81.46 (3)
O7—V1—V2	80.88 (2)	O13—V5—O14^i	77.01 (3)
O14^i—V1—V2	46.362 (16)	O12—V5—O14^i	77.00 (3)
V5—V1—V2	61.310 (6)	O3^i—V5—O14^i	74.30 (2)
O1—V1—V3	129.40 (3)	O5—V5—V1	137.01 (4)
O9—V1—V3	125.76 (2)	O9—V5—V1	32.96 (2)
O6—V1—V3	79.55 (2)	O13—V5—V1	83.39 (2)
O8—V1—V3	78.07 (2)	O12—V5—V1	84.06 (2)
O7—V1—V3	30.690 (19)	O3^i—V5—V1	122.825 (19)
O14^i—V1—V3	43.479 (15)	O14^i—V5—V1	48.521 (15)
V5—V1—V3	92.496 (6)	O5—V5—V3^i	131.12 (4)
V2—V1—V3	61.458 (5)	O9—V5—V3^i	124.81 (2)
O1—V1—V4	134.70 (3)	O13—V5—V3^i	78.32 (2)
O9—V1—V4	81.46 (2)	O12—V5—V3^i	78.62 (2)
O6—V1—V4	123.80 (2)	O3^i—V5—V3^i	30.960 (18)
O8—V1—V4	32.23 (2)	O14^i—V5—V3^i	43.346 (15)
O7—V1—V4	81.57 (2)	V1—V5—V3^i	91.865 (6)
O14^i—V1—V4	45.455 (15)	O5—V5—V4	135.05 (4)
V5—V1—V4	60.588 (6)	O9—V5—V4	80.99 (2)
V2—V1—V4	91.644 (6)	O13—V5—V4	122.29 (2)
V3—V1—V4	61.402 (5)	O12—V5—V4	32.23 (2)
O2—V2—O6	103.19 (4)	O3^i—V5—V4	81.44 (2)
O2—V2—O13	102.93 (4)	O14^i—V5—V4	45.285 (16)
O6—V2—O13	94.22 (3)	V1—V5—V4	60.308 (5)
O2—V2—O10	99.24 (4)	V3^i—V5—V4	61.383 (5)
O6—V2—O10	92.09 (3)	V3—O3—V5^i	109.98 (3)
O13—V2—O10	154.87 (3)	V2—O6—V1	113.89 (4)
O2—V2—O11^i	98.97 (4)	V3—O7—V1	111.12 (3)
O6—V2—O11^i	156.53 (3)	V4—O8—V1	114.22 (4)
O13—V2—O11^i	88.24 (3)	V1—O9—V5	113.76 (4)
O10—V2—O11^i	76.68 (3)	V3—O10—V2	107.49 (3)
O2—V2—O14^i	173.66 (3)	V3—O10—V4^i	106.61 (3)
O6—V2—O14^i	82.01 (3)	V2—O10—V4^i	100.95 (3)
O13—V2—O14^i	80.07 (3)	V3—O11—V2^i	107.71 (3)
O10—V2—O14^i	76.76 (3)	V3—O11—V4	107.45 (3)
O11^i—V2—O14^i	75.42 (3)	V2^i—O11—V4	99.49 (3)
O2—V2—V1	136.83 (3)	V4—O12—V5	113.89 (3)
O6—V2—V1	33.75 (2)	V2—O13—V5	115.19 (4)
O13—V2—V1	83.44 (2)	V3—O14—V3^i	102.04 (3)
O10—V2—V1	88.47 (2)	V3—O14—V4^i	93.65 (2)
O11^i—V2—V1	124.06 (2)	V3^i—O14—V4^i	93.42 (2)
O14^i—V2—V1	48.643 (16)	V3—O14—V2^i	93.73 (2)
O2—V2—V4^i	89.10 (3)	V3^i—O14—V2^i	92.47 (2)
O6—V2—V4^i	131.89 (3)	V4^i—O14—V2^i	169.39 (3)
O13—V2—V4^i	128.50 (2)	V3—O14—V1^i	169.74 (3)
O10—V2—V4^i	39.806 (19)	V3^i—O14—V1^i	88.20 (2)
O11^i—V2—V4^i	40.263 (18)	V4^i—O14—V1^i	86.38 (2)
O14^i—V2—V4^i	84.694 (17)	V2^i—O14—V1^i	84.99 (2)
V1—V2—V4^i	120.428 (6)	V3—O14—V5^i	87.30 (2)
O3—V3—O7	107.11 (4)	V3^i—O14—V5^i	170.66 (3)
O3—V3—O11	97.73 (3)	V4^i—O14—V5^i	86.25 (2)
O7—V3—O11	97.83 (3)	V2^i—O14—V5^i	86.50 (2)
O3—V3—O10	97.47 (3)	V1^i—O14—V5^i	82.46 (2)
O7—V3—O10	96.04 (3)	N2—C1—N1	118.43 (10)
O11—V3—O10	155.39 (3)	N2—C1—N3	123.86 (10)
O3—V3—O14	88.41 (3)	N1—C1—N3	117.57 (11)
O7—V3—O14	164.44 (3)	N4—C2—N5	118.72 (10)
O11—V3—O14	80.64 (3)	N4—C2—N3	123.49 (10)
O10—V3—O14	80.55 (3)	N5—C2—N3	117.62 (10)
O3—V3—O14^i	166.38 (3)	N5—C3—H3A	109.5
O7—V3—O14^i	86.51 (3)	N5—C3—H3B	109.5
O11—V3—O14^i	80.29 (3)	H3A—C3—H3B	109.5
O10—V3—O14^i	80.39 (3)	N5—C3—H3C	109.5
O14—V3—O14^i	77.96 (3)	H3A—C3—H3C	109.5
O3—V3—V5^i	39.06 (2)	H3B—C3—H3C	109.5
O7—V3—V5^i	146.17 (2)	N5—C4—H4A	109.5
O11—V3—V5^i	89.66 (2)	N5—C4—H4B	109.5
O10—V3—V5^i	90.04 (2)	H4A—C4—H4B	109.5
O14—V3—V5^i	49.358 (17)	N5—C4—H4C	109.5
O14^i—V3—V5^i	127.319 (17)	H4A—C4—H4C	109.5
O3—V3—V1	145.30 (3)	H4B—C4—H4C	109.5
O7—V3—V1	38.19 (2)	C1—N1—H1A	115.0 (14)
O11—V3—V1	89.69 (2)	C1—N1—H1B	119.0 (15)
O10—V3—V1	88.75 (2)	H1A—N1—H1B	126 (2)
O14—V3—V1	126.279 (18)	C1—N2—H2A	122.6 (12)
O14^i—V3—V1	48.321 (17)	C1—N2—H2B	119.7 (12)
V5^i—V3—V1	175.629 (6)	H2A—N2—H2B	114.9 (17)
O4—V4—O8	102.13 (4)	C1—N3—C2	122.59 (10)
O4—V4—O12	102.49 (4)	C2—N4—H4D	118.1 (12)
O8—V4—O12	95.66 (3)	C2—N4—H4E	117.1 (15)
O4—V4—O10^i	99.74 (4)	H4D—N4—H4E	124.7 (19)
O8—V4—O10^i	155.62 (3)	C2—N5—C3	122.03 (10)
O12—V4—O10^i	89.99 (3)	C2—N5—C4	120.63 (11)
O4—V4—O11	99.12 (4)	C3—N5—C4	117.34 (10)
O8—V4—O11	89.83 (3)	H6A—N6—H6B	106.4 (16)
O12—V4—O11	156.02 (3)	H6A—N6—H6C	108.3 (17)
O10^i—V4—O11	76.13 (3)	H6B—N6—H6C	117.5 (17)
O4—V4—O14^i	174.28 (3)	H6A—N6—H6D	109.4 (17)
O8—V4—O14^i	81.05 (3)	H6B—N6—H6D	107.1 (16)
O12—V4—O14^i	81.78 (3)	H6C—N6—H6D	108.0 (17)
O10^i—V4—O14^i	76.30 (2)	H7A—N7—H7B	109.0 (16)
O11—V4—O14^i	76.03 (3)	H7A—N7—H7C	109.8 (16)
O4—V4—V2^i	89.60 (3)	H7B—N7—H7C	109.4 (16)
O8—V4—V2^i	130.07 (2)	H7A—N7—H7D	112.0 (16)
O12—V4—V2^i	129.23 (2)	H7B—N7—H7D	111.8 (15)
O10^i—V4—V2^i	39.240 (19)	H7C—N7—H7D	104.8 (16)
O11—V4—V2^i	40.246 (19)	H15A—O15—H15B	112 (2)
O14^i—V4—V2^i	84.733 (17)	H16A—O16—H16B	112 (2)
O4—V4—V1	135.49 (3)	H17A—O17—H17B	102.5 (18)
O8—V4—V1	33.55 (2)
O7—V3—O3—V5^i	179.48 (4)	V3—V1—O9—V5	2.25 (5)
O11—V3—O3—V5^i	−79.82 (4)	V4—V1—O9—V5	47.45 (3)
O10—V3—O3—V5^i	80.77 (4)	O5—V5—O9—V1	178.29 (5)
O14—V3—O3—V5^i	0.51 (4)	O13—V5—O9—V1	75.08 (4)
O14^i—V3—O3—V5^i	0.80 (16)	O12—V5—O9—V1	−78.29 (4)
V1—V3—O3—V5^i	179.443 (13)	O3^i—V5—O9—V1	−3.32 (11)
O2—V2—O6—V1	−175.89 (4)	O14^i—V5—O9—V1	−1.51 (4)
O13—V2—O6—V1	−71.55 (4)	V3^i—V5—O9—V1	−1.85 (5)
O10—V2—O6—V1	84.11 (4)	V4—V5—O9—V1	−47.36 (3)
O11^i—V2—O6—V1	23.77 (10)	O4—V4—O12—V5	−174.54 (4)
O14^i—V2—O6—V1	7.80 (4)	O8—V4—O12—V5	−70.76 (4)
V4^i—V2—O6—V1	83.24 (4)	O10^i—V4—O12—V5	85.48 (4)
O1—V1—O6—V2	179.64 (4)	O11—V4—O12—V5	31.67 (9)
O9—V1—O6—V2	74.06 (4)	O14^i—V4—O12—V5	9.32 (4)
O8—V1—O6—V2	−23.07 (10)	V2^i—V4—O12—V5	85.57 (4)
O7—V1—O6—V2	−82.65 (4)	V1—V4—O12—V5	−39.17 (3)
O14^i—V1—O6—V2	−7.60 (4)	O5—V5—O12—V4	176.70 (5)
V5—V1—O6—V2	41.65 (4)	O9—V5—O12—V4	72.14 (4)
V3—V1—O6—V2	−51.93 (3)	O13—V5—O12—V4	−22.59 (9)
V4—V1—O6—V2	−7.11 (5)	O3^i—V5—O12—V4	−84.33 (4)
O3—V3—O7—V1	−179.96 (4)	O14^i—V5—O12—V4	−8.99 (3)
O11—V3—O7—V1	79.41 (4)	V1—V5—O12—V4	39.76 (3)
O10—V3—O7—V1	−80.21 (4)	V3^i—V5—O12—V4	−53.35 (3)
O14—V3—O7—V1	−3.81 (14)	O2—V2—O13—V5	175.65 (4)
O14^i—V3—O7—V1	−0.27 (4)	O6—V2—O13—V5	71.08 (4)
V5^i—V3—O7—V1	−179.378 (13)	O10—V2—O13—V5	−33.02 (10)
O4—V4—O8—V1	174.69 (4)	O11^i—V2—O13—V5	−85.55 (4)
O12—V4—O8—V1	70.60 (4)	O14^i—V2—O13—V5	−10.04 (4)
O10^i—V4—O8—V1	−32.00 (10)	V1—V2—O13—V5	39.04 (3)
O11—V4—O8—V1	−86.02 (4)	V4^i—V2—O13—V5	−85.02 (4)
O14^i—V4—O8—V1	−10.14 (4)	O5—V5—O13—V2	−175.94 (5)
V2^i—V4—O8—V1	−85.43 (4)	O9—V5—O13—V2	−71.13 (4)
V5—V4—O8—V1	38.66 (3)	O12—V5—O13—V2	23.31 (10)
O1—V1—O8—V4	−177.47 (4)	O3^i—V5—O13—V2	85.00 (4)
O9—V1—O8—V4	−72.00 (4)	O14^i—V5—O13—V2	9.71 (4)
O6—V1—O8—V4	25.37 (10)	V1—V5—O13—V2	−39.18 (3)
O7—V1—O8—V4	85.10 (4)	V3^i—V5—O13—V2	54.11 (3)
O14^i—V1—O8—V4	9.83 (3)	V4—V5—O13—V2	9.28 (5)
V5—V1—O8—V4	−39.33 (3)	N2—C1—N3—C2	30.11 (19)
V2—V1—O8—V4	10.82 (5)	N1—C1—N3—C2	−154.27 (13)
V3—V1—O8—V4	54.39 (3)	N4—C2—N3—C1	34.71 (19)
O1—V1—O9—V5	−178.43 (4)	N5—C2—N3—C1	−150.09 (12)
O6—V1—O9—V5	−76.42 (4)	N4—C2—N5—C3	−178.69 (15)
O8—V1—O9—V5	78.31 (4)	N3—C2—N5—C3	5.88 (19)
O7—V1—O9—V5	3.13 (11)	N4—C2—N5—C4	2.39 (18)
O14^i—V1—O9—V5	1.52 (4)	N3—C2—N5—C4	−173.04 (12)
V2—V1—O9—V5	−45.22 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O10^ii	0.818 (19)	2.080 (19)	2.8981 (12)	178 (2)
N1—H1B···O6	0.76 (2)	2.71 (2)	3.4507 (15)	163.9 (19)
N2—H2A···O12^iii	0.854 (18)	2.112 (18)	2.9457 (12)	165.4 (17)
N2—H2B···O15^iv	0.849 (19)	2.072 (19)	2.9164 (16)	172.9 (17)
N4—H4D···O9^iv	0.912 (19)	2.423 (19)	3.2993 (14)	161.1 (16)
N4—H4E···O16^v	0.736 (19)	2.269 (19)	2.9686 (16)	159.2 (19)
N6—H6A···O8^vi	0.882 (19)	1.865 (19)	2.7463 (13)	176.7 (17)
N6—H6B···O17^ii	0.874 (18)	1.921 (19)	2.7871 (13)	170.7 (17)
N6—H6C···O7	0.808 (19)	1.990 (19)	2.7922 (11)	172.2 (18)
N6—H6D···O2^ii	0.873 (19)	2.074 (19)	2.8541 (13)	148.3 (16)
N7—H7A···O16	0.835 (18)	2.083 (18)	2.8810 (14)	159.8 (17)
N7—H7B···O2^vii	0.880 (18)	2.367 (17)	2.9194 (12)	121.1 (14)
N7—H7B···O4^viii	0.880 (18)	2.056 (18)	2.8627 (12)	152.1 (16)
N7—H7C···O1^ix	0.843 (19)	2.072 (19)	2.9050 (12)	169.7 (17)
N7—H7D···O11^i	0.873 (18)	1.928 (18)	2.7957 (12)	172.1 (16)
O15—H15A···O4	0.81 (2)	2.52 (2)	3.0266 (14)	122 (2)
O15—H15A···O12	0.81 (2)	2.38 (2)	3.1833 (16)	171 (2)
O15—H15B···O17^x	0.78 (2)	2.03 (2)	2.8046 (18)	177 (3)
O16—H16A···O15^viii	0.80 (2)	2.05 (2)	2.8477 (18)	176 (2)
O16—H16B···O5^xi	0.83 (2)	2.23 (2)	2.8937 (13)	137 (2)
O17—H17A···O13	0.85 (1)	1.87 (2)	2.7130 (12)	172 (2)
O17—H17B···N3	0.82 (2)	2.07 (2)	2.8830 (15)	170 (2)

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