(L-Histidinato-κ³N,N,O)(L-histidine-κ²N,O)oxido­vanadium(IV) perchlorate monohydrate

The first homoleptic oxovanadium(IV)–histidine complex {systematic name: [(S*)-α-amino-4-imidazole­propionato-κ³N,N,O][(S*)-α-amino-3-(1H-imidazol-3-ium-5-yl)propionato-κ²N,O]oxovanadium(IV) perchlorate monohydrate}, [V^IVO(C₆H₈N₃O₂)(C₆H₉N₃O₂)]ClO₄·H₂O, adopts a distorted octa­hedral structure where one L-histidine ligand coordinates to the vanadium(IV) center in a tridentate fashion as a monoanion and the other in a bidentate fashion leaving a protonated imidazole group as a pendent group.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in solvent or counterion
• R factor = 0.030
• wR factor = 0.088
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O1     ..  O9      ..       2.77 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.655     0.752
            Tmin(prime) and Tmax expected:      0.745     0.752
            RR(prime) =      0.878
            Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.86
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl2
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      45.00 Perc.
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.02

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.48
           From the CIF: _reflns_number_total               4461
           Count of symmetry unique reflns         2574
           Completeness (_total/calc)            173.31%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1887
           Fraction of Friedel pairs measured     0.733
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          S

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

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

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Computing details

Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999) and DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: CrystalStructure.

(α-amino-4-imidazolepropionato-κ³N,N,O)[α-amino-3-(1H-imidazol-3-ium- 5-yl)propionato-κ²N,O]oxovanadium(IV) perchlorate monohydrate

Crystal data

[VO(C6H8N3O2)(C6H9N3O2)]·ClO4·H2O	F(000) = 1012.00
Mr = 493.71	Dx = 1.688 Mg m^−3
Orthorhombic, P21212	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2 2ab	Cell parameters from 6453 reflections
a = 10.5044 (2) Å	θ = 3.1–27.5°
b = 25.4158 (8) Å	µ = 0.71 mm^−1
c = 7.2779 (2) Å	T = 296 K
V = 1943.04 (9) Å^3	Block, blue
Z = 4	0.40 × 0.40 × 0.40 mm

Data collection

Rigaku Mercury diffractometer	4296 reflections with F^2 > 2σ(F^2)
Detector resolution: 7.31 pixels mm^-1	Rint = 0.022
ω scans	θmax = 27.5°
Absorption correction: multi-scan (Jacobson, 1998)	h = −13→13
Tmin = 0.655, Tmax = 0.752	k = −33→20
15642 measured reflections	l = −9→9
4461 independent reflections

Refinement

Refinement on F^2	w = 1/[0.001Fo^2 + σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.030	(Δ/σ)max < 0.001
wR(F^2) = 0.088	Δρmax = 0.61 e Å^−3
S = 1.01	Δρmin = −0.49 e Å^−3
4461 reflections	Absolute structure: Flack (1983), 1892 Friedel pairs
336 parameters	Absolute structure parameter: 0.000 (17)
H-atom parameters constrained

Special details

Experimental. Characteristic IR bands (cm^-1) (KBr pellets, JASCO FT/IR-8000S spectrometer): 1636, ν_as(COO^-); 1433, ν_s(COO^-), 1112 and 1083, ν(ClO₄^-); 977, ν(V=O). Other bands with medium to strong intensities are: 1384(s), 1348(m), 1324(m), 1272(m), 1239(m), 929(m), 835(m), 752(m) and 626(s).

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
V1	0.15655 (3)	0.121510 (10)	0.37283 (4)	0.02514 (6)
Cl1	0.51650 (14)	0.49154 (4)	0.12857 (13)	0.0394 (3)	0.50
Cl2	0.0166 (3)	0.50474 (15)	−0.02673 (14)	0.0474 (5)	0.50
O1	0.10984 (14)	0.06193 (6)	0.3815 (2)	0.0441 (3)
O2	0.22482 (13)	0.19929 (5)	0.2994 (2)	0.0335 (3)
O3	0.18817 (14)	0.26796 (6)	0.1192 (2)	0.0429 (3)
O4	0.20232 (12)	0.14126 (6)	0.6284 (2)	0.0361 (3)
O5	0.35001 (14)	0.14805 (8)	0.8433 (2)	0.0467 (4)
O6	0.54381 (16)	0.16735 (7)	0.0943 (2)	0.0497 (4)
O7	0.4409 (2)	0.44490 (9)	0.1022 (4)	0.0569 (10)	0.50
O8	0.64816 (17)	0.47705 (11)	0.1484 (5)	0.0827 (15)	0.50
O9	0.4746 (3)	0.51849 (12)	0.2915 (3)	0.0918 (18)	0.50
O10	0.5023 (3)	0.52567 (12)	−0.0278 (3)	0.1019 (19)	0.50
O11	−0.0756 (4)	0.5401 (2)	0.0515 (6)	0.0801 (17)	0.50
O12	−0.0173 (6)	0.4934 (2)	−0.2142 (3)	0.100 (2)	0.50
O13	0.1405 (3)	0.5289 (2)	−0.0217 (9)	0.145 (3)	0.50
O14	0.0190 (7)	0.4566 (2)	0.0773 (8)	0.184 (5)	0.50
N1	0.12784 (16)	0.13009 (7)	0.0851 (2)	0.0325 (3)
N2	−0.01798 (14)	0.15969 (6)	0.4076 (2)	0.0298 (3)
N3	−0.16415 (18)	0.20113 (8)	0.5622 (2)	0.0460 (4)
N4	0.35828 (14)	0.10760 (7)	0.3693 (2)	0.0321 (3)
N5	0.67407 (16)	0.09755 (7)	0.3085 (2)	0.0361 (4)
N6	0.79392 (19)	0.03855 (8)	0.4243 (4)	0.0552 (6)
C1	0.17503 (16)	0.22077 (7)	0.1597 (2)	0.0299 (4)
C2	0.09193 (18)	0.18507 (8)	0.0423 (2)	0.0318 (4)
C3	−0.04886 (18)	0.19513 (9)	0.0873 (2)	0.0381 (5)
C4	−0.08006 (17)	0.19303 (7)	0.2882 (3)	0.0315 (4)
C5	−0.16987 (19)	0.21953 (8)	0.3853 (3)	0.0452 (5)
C6	−0.0722 (2)	0.16548 (10)	0.5712 (3)	0.0393 (5)
C7	0.31537 (17)	0.13436 (8)	0.6885 (2)	0.0313 (4)
C8	0.40801 (17)	0.10580 (7)	0.5600 (2)	0.0295 (4)
C9	0.54316 (17)	0.12708 (9)	0.5803 (3)	0.0373 (4)
C10	0.64311 (17)	0.09431 (8)	0.4916 (2)	0.0325 (4)
C11	0.7189 (2)	0.05668 (10)	0.5640 (4)	0.0504 (6)
C12	0.7652 (2)	0.06303 (10)	0.2724 (4)	0.0502 (6)
H1	0.1994	0.1220	0.0261	0.039*
H2	0.0659	0.1086	0.0490	0.039*
H3	−0.2119	0.2110	0.6517	0.055*
H4	0.3740	0.0770	0.3139	0.039*
H5	0.3967	0.1334	0.3081	0.039*
H6	0.6399	0.1186	0.2301	0.044*
H7	0.8513	0.0146	0.4349	0.067*
H8	0.1074	0.1922	−0.0868	0.039*
H9	−0.0714	0.2298	0.0417	0.046*
H10	−0.0995	0.1687	0.0248	0.046*
H11	−0.2247	0.2452	0.3404	0.055*
H12	−0.0491	0.1472	0.6768	0.048*
H13	0.4097	0.0692	0.5971	0.036*
H14	0.5460	0.1619	0.5258	0.045*
H15	0.5625	0.1296	0.7103	0.045*
H16	0.7199	0.0453	0.6855	0.060*
H17	0.8024	0.0573	0.1582	0.060*
H18	0.5963	0.1862	0.0346	0.060*
H19	0.4967	0.1506	0.0195	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
V1	0.02251 (13)	0.02744 (14)	0.02546 (14)	0.00414 (10)	0.00094 (11)	−0.00189 (11)
Cl1	0.0507 (8)	0.0345 (8)	0.0329 (3)	0.0022 (5)	0.0050 (5)	−0.0010 (4)
Cl2	0.0616 (18)	0.0415 (13)	0.0391 (4)	−0.0041 (10)	0.0055 (6)	0.0006 (6)
O1	0.0424 (7)	0.0311 (6)	0.0590 (9)	0.0032 (5)	0.0042 (7)	0.0029 (7)
O2	0.0335 (6)	0.0331 (6)	0.0340 (6)	−0.0045 (5)	−0.0092 (5)	−0.0017 (5)
O3	0.0374 (7)	0.0359 (6)	0.0552 (9)	−0.0061 (5)	−0.0071 (7)	0.0098 (7)
O4	0.0268 (5)	0.0571 (8)	0.0245 (5)	0.0113 (5)	0.0012 (5)	−0.0019 (6)
O5	0.0320 (6)	0.0788 (11)	0.0294 (7)	0.0061 (7)	−0.0001 (6)	−0.0070 (6)
O6	0.0512 (9)	0.0584 (9)	0.0396 (8)	−0.0122 (7)	−0.0087 (7)	0.0164 (7)
O7	0.0443 (17)	0.057 (2)	0.069 (2)	−0.0059 (15)	0.0063 (17)	−0.0224 (18)
O8	0.051 (2)	0.071 (2)	0.126 (4)	−0.0017 (19)	−0.027 (2)	−0.015 (2)
O9	0.138 (5)	0.075 (3)	0.062 (2)	−0.023 (3)	0.039 (3)	−0.037 (2)
O10	0.133 (4)	0.093 (3)	0.080 (3)	0.048 (3)	0.042 (3)	0.047 (2)
O11	0.085 (3)	0.109 (4)	0.045 (2)	0.014 (3)	0.003 (2)	−0.032 (2)
O12	0.167 (6)	0.072 (4)	0.062 (2)	0.051 (4)	−0.069 (4)	−0.031 (3)
O13	0.125 (5)	0.133 (6)	0.179 (8)	−0.047 (5)	0.053 (5)	−0.033 (6)
O14	0.230 (13)	0.132 (7)	0.190 (10)	0.053 (7)	0.107 (9)	0.102 (7)
N1	0.0329 (7)	0.0391 (8)	0.0254 (7)	−0.0055 (6)	0.0017 (5)	−0.0088 (5)
N2	0.0246 (6)	0.0356 (7)	0.0291 (7)	0.0045 (5)	0.0001 (5)	−0.0046 (5)
N3	0.0324 (8)	0.0552 (10)	0.0503 (10)	0.0099 (8)	0.0076 (8)	−0.0203 (8)
N4	0.0244 (6)	0.0418 (7)	0.0301 (7)	0.0063 (5)	0.0022 (6)	−0.0036 (6)
N5	0.0301 (8)	0.0388 (8)	0.0395 (8)	0.0020 (6)	0.0058 (7)	−0.0009 (6)
N6	0.0302 (8)	0.0380 (9)	0.0974 (19)	0.0112 (7)	0.0040 (10)	−0.0022 (10)
C1	0.0233 (7)	0.0329 (8)	0.0336 (9)	−0.0029 (6)	−0.0002 (6)	0.0002 (6)
C2	0.0308 (8)	0.0427 (9)	0.0221 (8)	−0.0057 (7)	−0.0032 (7)	0.0023 (7)
C3	0.0267 (8)	0.0517 (11)	0.0360 (10)	−0.0047 (8)	−0.0086 (7)	0.0067 (8)
C4	0.0217 (7)	0.0304 (8)	0.0424 (10)	−0.0010 (6)	−0.0051 (7)	−0.0015 (7)
C5	0.0294 (8)	0.0360 (9)	0.0702 (14)	0.0095 (7)	−0.0027 (11)	−0.0058 (10)
C6	0.0298 (8)	0.0566 (12)	0.0316 (9)	0.0032 (9)	0.0027 (7)	−0.0075 (8)
C7	0.0263 (8)	0.0418 (9)	0.0259 (8)	0.0057 (7)	0.0020 (6)	0.0033 (7)
C8	0.0236 (7)	0.0354 (8)	0.0296 (8)	0.0066 (6)	0.0006 (6)	0.0010 (6)
C9	0.0255 (8)	0.0467 (10)	0.0399 (10)	0.0060 (8)	−0.0007 (7)	−0.0092 (8)
C10	0.0214 (7)	0.0383 (9)	0.0379 (9)	0.0025 (7)	−0.0002 (7)	0.0008 (7)
C11	0.0345 (10)	0.0522 (12)	0.0643 (15)	0.0081 (9)	−0.0037 (10)	0.0173 (11)
C12	0.0350 (10)	0.0468 (12)	0.0688 (16)	−0.0010 (9)	0.0148 (11)	−0.0161 (12)

Geometric parameters (Å, º)

V1—O1	1.5930 (15)	C1—C2	1.522 (2)
V1—O2	2.1698 (13)	C2—C3	1.536 (2)
V1—O4	1.9860 (14)	C3—C4	1.499 (3)
V1—N1	2.1267 (15)	C4—C5	1.358 (2)
V1—N2	2.0897 (15)	C7—C8	1.533 (2)
V1—N4	2.1485 (15)	C8—C9	1.526 (2)
Cl1—O7	1.440 (2)	C9—C10	1.487 (2)
Cl1—O8	1.438 (2)	C10—C11	1.351 (3)
Cl1—O9	1.438 (2)	O6—H18	0.850
Cl1—O10	1.439 (2)	O6—H19	0.850
Cl2—O11	1.439 (6)	N1—H1	0.890
Cl2—O12	1.439 (3)	N1—H2	0.890
Cl2—O13	1.439 (5)	N3—H3	0.860
Cl2—O14	1.439 (6)	N4—H4	0.890
O2—C1	1.267 (2)	N4—H5	0.890
O3—C1	1.243 (2)	N5—H6	0.860
O4—C7	1.278 (2)	N6—H7	0.860
O5—C7	1.234 (2)	C2—H8	0.970
N1—C2	1.481 (2)	C3—H9	0.970
N2—C4	1.378 (2)	C3—H10	0.970
N2—C6	1.328 (2)	C5—H11	0.930
N3—C5	1.371 (3)	C6—H12	0.930
N3—C6	1.326 (3)	C8—H13	0.970
N4—C8	1.484 (2)	C9—H14	0.970
N5—C10	1.374 (2)	C9—H15	0.970
N5—C12	1.325 (2)	C11—H16	0.930
N6—C11	1.367 (3)	C12—H17	0.930
N6—C12	1.304 (3)
O1···O9^i	2.769 (3)	N1···O5^viii	2.958 (2)
O1···O10^ii	2.977 (3)	N1···O7^v	3.058 (3)
O1···N6^iii	2.764 (2)	N1···O10^ii	3.014 (3)
O2···N3^iv	2.963 (2)	N3···O2^xi	2.963 (2)
O3···O6^v	2.723 (2)	N3···O3^xi	2.899 (2)
O3···N3^iv	2.899 (2)	N4···O6	3.180 (2)
O5···O6^vi	2.779 (2)	N4···O12^vii	3.094 (7)
O5···N1^vi	2.958 (2)	N5···O6	2.730 (2)
O6···O3^vii	2.723 (2)	N5···O11^ii	3.173 (5)
O6···O5^viii	2.779 (2)	N5···O12^vii	3.139 (7)
O6···N4	3.180 (2)	N5···O12^ii	3.192 (7)
O6···N5	2.730 (2)	N6···O1^iii	2.764 (2)
O7···Cl1	1.440 (2)	N6···O9^iv	3.160 (3)
O7···N1^vii	3.058 (3)	O1···H7^iii	2.025
O8···Cl1	1.438 (2)	O3···H3^iv	2.042
O8···O13^ix	2.546 (5)	O3···H18^v	1.882
O9···Cl1	1.438 (2)	O5···H1^vi	2.171
O9···O1^x	2.769 (3)	O5···H19^vi	2.005
O9···N6^xi	3.160 (3)	O6···H5	2.357
O10···Cl1	1.439 (2)	O6···H6	1.880
O10···O1^xii	2.977 (3)	O7···H2^vii	2.187
O10···N1^xii	3.014 (3)	O7···H17^v	2.389
O11···Cl2	1.439 (6)	O10···H2^xii	2.230
O11···O12	2.350 (7)	O10···H17^xiii	2.398
O11···N5^xii	3.173 (5)	O12···H4^v	2.244
O11···C12^xii	3.141 (5)	H1···O5^viii	2.171
O12···O11	2.350 (7)	H2···O7^v	2.187
O12···O13	2.350 (7)	H2···O10^ii	2.230
O12···O14	2.350 (7)	H3···O3^xi	2.042
O12···N4^v	3.094 (7)	H4···O12^vii	2.244
O12···N5^v	3.139 (7)	H5···O6	2.357
O12···N5^xii	3.192 (7)	H6···O6	1.880
O12···C12^xii	3.177 (7)	H7···O1^iii	2.025
O13···Cl2	1.439 (5)	H17···O7^vii	2.389
O13···O8^ix	2.546 (5)	H17···O10^xiv	2.398
O13···O12	2.350 (7)	H18···O3^vii	1.882
O14···Cl2	1.439 (6)	H19···O5^viii	2.005
O14···O12	2.350 (7)
O1—V1—O2	167.84 (7)	O5—C7—C8	120.23 (16)
O1—V1—O4	106.13 (8)	N4—C8—C7	109.44 (14)
O1—V1—N1	95.32 (8)	N4—C8—C9	114.00 (15)
O1—V1—N2	99.58 (6)	C7—C8—C9	111.34 (15)
O1—V1—N4	98.50 (7)	C8—C9—C10	114.60 (17)
O2—V1—O4	85.44 (5)	N5—C10—C9	123.66 (17)
O2—V1—N1	73.19 (6)	N5—C10—C11	106.33 (19)
O2—V1—N2	84.07 (5)	C9—C10—C11	130.0 (2)
O2—V1—N4	79.69 (6)	N6—C11—C10	106.7 (2)
O4—V1—N1	158.55 (6)	N5—C12—N6	108.3 (2)
O4—V1—N2	88.94 (5)	H18—O6—H19	109.5
O4—V1—N4	79.29 (5)	V1—N1—H1	109.4
N1—V1—N2	86.98 (6)	V1—N1—H2	109.4
N1—V1—N4	98.33 (6)	C2—N1—H1	109.4
N2—V1—N4	160.59 (6)	C2—N1—H2	109.4
O7—Cl1—O8	109.46 (16)	H1—N1—H2	109.5
O7—Cl1—O9	109.47 (19)	C5—N3—H3	125.9
O7—Cl1—O10	109.47 (19)	C6—N3—H3	125.9
O8—Cl1—O9	109.5 (2)	V1—N4—H4	109.4
O8—Cl1—O10	109.5 (2)	V1—N4—H5	109.4
O9—Cl1—O10	109.48 (18)	C8—N4—H4	109.4
O11—Cl2—O12	109.5 (3)	C8—N4—H5	109.4
O11—Cl2—O13	109.5 (4)	H4—N4—H5	109.5
O11—Cl2—O14	109.5 (3)	C10—N5—H6	125.5
O12—Cl2—O13	109.5 (3)	C12—N5—H6	125.6
O12—Cl2—O14	109.5 (4)	C11—N6—H7	125.2
O13—Cl2—O14	109.5 (4)	C12—N6—H7	125.2
V1—O2—C1	116.99 (11)	N1—C2—H8	109.7
V1—O4—C7	120.72 (12)	C1—C2—H8	109.7
V1—N1—C2	109.90 (11)	C3—C2—H8	109.7
V1—N2—C4	128.63 (12)	C2—C3—H9	108.2
V1—N2—C6	122.44 (13)	C2—C3—H10	108.2
C4—N2—C6	107.12 (16)	C4—C3—H9	108.2
C5—N3—C6	108.17 (18)	C4—C3—H10	108.2
V1—N4—C8	109.94 (11)	H9—C3—H10	109.5
C10—N5—C12	108.89 (19)	N3—C5—H11	126.6
C11—N6—C12	109.7 (2)	C4—C5—H11	126.6
O2—C1—O3	124.11 (17)	N2—C6—H12	125.0
O2—C1—C2	115.51 (15)	N3—C6—H12	125.0
O3—C1—C2	120.36 (17)	N4—C8—H13	107.2
N1—C2—C1	107.35 (14)	C7—C8—H13	107.2
N1—C2—C3	110.94 (16)	C9—C8—H13	107.3
C1—C2—C3	109.45 (15)	C8—C9—H14	108.2
C2—C3—C4	114.37 (16)	C8—C9—H15	108.2
N2—C4—C3	122.25 (16)	C10—C9—H14	108.2
N2—C4—C5	107.79 (19)	C10—C9—H15	108.2
C3—C4—C5	129.93 (19)	H14—C9—H15	109.5
N3—C5—C4	106.80 (18)	N6—C11—H16	126.6
N2—C6—N3	110.09 (19)	C10—C11—H16	126.6
O4—C7—O5	123.22 (17)	N5—C12—H17	125.8
O4—C7—C8	116.51 (16)	N6—C12—H17	125.8
O1—V1—O2—C1	46.4 (3)	V1—N2—C4—C3	18.5 (2)
O1—V1—O4—C7	90.03 (15)	V1—N2—C4—C5	−163.27 (13)
O1—V1—N1—C2	148.17 (12)	V1—N2—C6—N3	165.12 (13)
O1—V1—N2—C4	−117.85 (16)	C4—N2—C6—N3	−0.8 (2)
O1—V1—N2—C6	79.51 (17)	C6—N2—C4—C3	−176.77 (18)
O1—V1—N4—C8	−89.49 (13)	C6—N2—C4—C5	1.5 (2)
O2—V1—O4—C7	−86.17 (15)	C5—N3—C6—N2	−0.2 (2)
O4—V1—O2—C1	−151.24 (13)	C6—N3—C5—C4	1.1 (2)
O2—V1—N1—C2	−35.90 (11)	V1—N4—C8—C7	−21.46 (17)
N1—V1—O2—C1	26.79 (12)	V1—N4—C8—C9	−146.87 (13)
O2—V1—N2—C4	50.45 (15)	C10—N5—C12—N6	−0.6 (2)
O2—V1—N2—C6	−112.20 (16)	C12—N5—C10—C9	−179.37 (19)
N2—V1—O2—C1	−61.83 (13)	C12—N5—C10—C11	0.03 (17)
O2—V1—N4—C8	102.70 (12)	C11—N6—C12—N5	0.9 (2)
N4—V1—O2—C1	128.84 (13)	C12—N6—C11—C10	−0.8 (2)
O4—V1—N1—C2	−30.5 (2)	O2—C1—C2—N1	−20.0 (2)
N1—V1—O4—C7	−91.3 (2)	O2—C1—C2—C3	100.47 (19)
O4—V1—N2—C4	135.97 (15)	O3—C1—C2—N1	161.67 (16)
O4—V1—N2—C6	−26.67 (16)	O3—C1—C2—C3	−77.8 (2)
N2—V1—O4—C7	−170.31 (15)	N1—C2—C3—C4	67.1 (2)
O4—V1—N4—C8	15.44 (11)	C1—C2—C3—C4	−51.2 (2)
N4—V1—O4—C7	−5.82 (15)	C2—C3—C4—N2	−33.4 (2)
N1—V1—N2—C4	−22.96 (15)	C2—C3—C4—C5	148.9 (2)
N1—V1—N2—C6	174.40 (17)	N2—C4—C5—N3	−1.6 (2)
N2—V1—N1—C2	48.82 (12)	C3—C4—C5—N3	176.47 (19)
N1—V1—N4—C8	173.81 (12)	O4—C7—C8—N4	18.5 (2)
N4—V1—N1—C2	−112.41 (12)	O4—C7—C8—C9	145.46 (18)
N2—V1—N4—C8	69.0 (2)	O5—C7—C8—N4	−163.60 (18)
N4—V1—N2—C4	83.7 (2)	O5—C7—C8—C9	−36.7 (2)
N4—V1—N2—C6	−78.9 (2)	N4—C8—C9—C10	−68.1 (2)
V1—O2—C1—O3	167.36 (14)	C7—C8—C9—C10	167.46 (16)
V1—O2—C1—C2	−10.88 (19)	C8—C9—C10—N5	83.7 (2)
V1—O4—C7—O5	176.75 (16)	C8—C9—C10—C11	−95.5 (2)
V1—O4—C7—C8	−5.4 (2)	N5—C10—C11—N6	0.5 (2)
V1—N1—C2—C1	41.25 (16)	C9—C10—C11—N6	179.8 (2)
V1—N1—C2—C3	−78.29 (16)

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