Di-μ-oxido-bis-({2-[(R,R)-(-)-(2-amino-cyclo-hexyl)imino-meth-yl]-4-nitro-phenolato-κN,N',O}oxidovanadium(V)) dimethyl sulfoxide disolvate.

The title compound, [V(2)(C(13)H(16)N(3)O(3))(2)O(4)]·2C(2)H(6)OS, is a centrosymmetric dimeric complex solvated by two dimethyl sulfoxide mol-ecules. Each V(V) atom is six-coordinated by one oxide group, two N atoms and one O atom from the tridentate Schiff base ligand, and by two additional bridging O atoms in a distorted octa-hedral coordination geometry. Three atoms of the cyclo-hexane ring are each disordered over two sites, with occupancy factors of 0.501 (10) and 0.499 (10). C-H⋯O and N-H⋯O hydrogen bonds link the dimers and solvent mol-ecules into a supra-molecular network.

Related literature

For general background, see: Carter-Franklin et al. (2003 ▶); Eady (2003 ▶); Evangelou (2002 ▶); Mendz (1991 ▶); Parekh et al. (2006 ▶); Rao et al. (1981 ▶); Rehder et al. (2002 ▶, 2003 ▶); Shahzadi et al. (2007 ▶). For related structures, see: Kwiatkowski et al. (2007 ▶); Mokry & Carrano (1993 ▶); Romanowski et al. (2008 ▶); Root et al. (1993 ▶). For the synthesis, see: Kwiatkowski et al. (2003 ▶).

Experimental

Crystal data

[V2(C13H16N3O3)2O4]·2C2H6OS

M = 846.71

Triclinic,

a = 7.249 (1) Å

b = 11.747 (2) Å

c = 11.809 (2) Å

α = 77.69 (3)°

β = 88.62 (3)°

γ = 76.13 (3)°

V = 953.4 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.67 mm−1

T = 295 (2) K

0.60 × 0.25 × 0.10 mm

Data collection

Oxford Diffraction Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.720, T max = 0.936

6786 measured reflections

3355 independent reflections

3245 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.079

wR(F 2) = 0.194

S = 1.44

3355 reflections

256 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.44 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038762/hy2164sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038762/hy2164Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[V2(C13H16N3O3)2O4]·2C2H6OS	Z = 1
Mr = 846.71	F(000) = 440
Triclinic, P1	Dx = 1.475 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.249 (1) Å	Cell parameters from 3355 reflections
b = 11.747 (2) Å	θ = 3.0–25.1°
c = 11.809 (2) Å	µ = 0.67 mm−1
α = 77.69 (3)°	T = 295 K
β = 88.62 (3)°	Needle, yellow
γ = 76.13 (3)°	0.60 × 0.25 × 0.10 mm
V = 953.4 (3) Å3

Oxford Diffraction Ruby CCD diffractometer	3355 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3245 reflections with I > 2σ(I)
graphite	Rint = 0.021
Detector resolution: 10.4002 pixels mm-1	θmax = 25.1°, θmin = 3.0°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −13→11
Tmin = 0.720, Tmax = 0.936	l = −13→14
6786 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.079	H-atom parameters constrained
wR(F2) = 0.194	w = 1/[σ2(Fo2) + (0.0232P)2 + 4.2049P] where P = (Fo2 + 2Fc2)/3
S = 1.44	(Δ/σ)max < 0.001
3355 reflections	Δρmax = 0.53 e Å−3
256 parameters	Δρmin = −0.44 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0061 (16)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.1768 (8)	0.7547 (5)	0.8238 (5)	0.0318 (12)
C2	0.3625 (8)	0.7030 (5)	0.7934 (5)	0.0322 (12)
C3	0.4761 (10)	0.7777 (6)	0.7378 (6)	0.0448 (15)
H3A	0.5999	0.7450	0.7188	0.054*
C4	0.4032 (11)	0.8999 (6)	0.7112 (6)	0.0505 (17)
C5	0.2207 (11)	0.9522 (6)	0.7375 (6)	0.0525 (18)
H5A	0.1727	1.0348	0.7155	0.063*
C6	0.1108 (10)	0.8802 (5)	0.7969 (5)	0.0403 (14)
H6A	−0.0095	0.9151	0.8197	0.048*
N7	0.5242 (12)	0.9771 (6)	0.6526 (7)	0.077 (2)
O8	0.4474 (11)	1.0817 (5)	0.6099 (7)	0.103 (3)
O9	0.6933 (10)	0.9331 (6)	0.6482 (8)	0.101 (3)
C10	0.4411 (8)	0.5748 (5)	0.8148 (5)	0.0335 (13)
H10A	0.5713	0.5473	0.8071	0.040*
N11	0.3421 (7)	0.4965 (4)	0.8437 (4)	0.0329 (11)
C12	0.436 (2)	0.3677 (13)	0.8877 (13)	0.030 (3)	0.501 (10)
H12A	0.4263	0.3496	0.9722	0.036*	0.501 (10)
C12A	0.428 (2)	0.3682 (13)	0.8308 (15)	0.032 (3)	0.499 (10)
H12B	0.4040	0.3614	0.7515	0.038*	0.499 (10)
C13	0.6421 (8)	0.3255 (5)	0.8594 (6)	0.0405 (14)
H13A	0.6607	0.3629	0.7798	0.049*
H13B	0.7202	0.3522	0.9090	0.049*
C14	0.7089 (11)	0.1916 (6)	0.8742 (9)	0.070 (2)
H14A	0.8251	0.1749	0.8318	0.083*
H14B	0.7415	0.1579	0.9557	0.083*
C15	0.5840 (19)	0.1297 (11)	0.8390 (14)	0.048 (4)	0.501 (10)
H15A	0.6353	0.0441	0.8656	0.058*	0.501 (10)
H15B	0.5754	0.1470	0.7550	0.058*	0.501 (10)
C15A	0.595 (2)	0.1146 (13)	0.9356 (14)	0.054 (4)*	0.499 (10)
H15C	0.6012	0.1126	1.0180	0.064*	0.499 (10)
H15D	0.6433	0.0335	0.9240	0.064*	0.499 (10)
C16	0.3804 (10)	0.1654 (6)	0.8875 (8)	0.057 (2)
H16A	0.3852	0.1485	0.9715	0.069*
H16B	0.2972	0.1216	0.8621	0.069*
C17	0.3085 (16)	0.3038 (10)	0.8368 (11)	0.032 (3)	0.501 (10)
H17A	0.3097	0.3219	0.7519	0.038*	0.501 (10)
C17A	0.3189 (16)	0.2942 (10)	0.9138 (13)	0.033 (3)*	0.499 (10)
H17B	0.3453	0.2941	0.9948	0.040*	0.499 (10)
N18	0.1126 (7)	0.3474 (4)	0.8793 (4)	0.0361 (11)
H18A	0.1072	0.3108	0.9541	0.043*
H18B	0.0280	0.3264	0.8382	0.043*
V19	0.03456 (13)	0.53484 (9)	0.86534 (8)	0.0289 (3)
O20	−0.0303 (7)	0.5634 (4)	0.7308 (4)	0.0490 (12)
O21	0.1601 (5)	0.4698 (4)	1.0582 (3)	0.0325 (9)
O22	0.0653 (6)	0.6894 (3)	0.8812 (3)	0.0364 (9)
S23	−0.0005 (3)	0.6916 (2)	0.44455 (18)	0.0657 (6)
C24	0.0490 (17)	0.8021 (9)	0.5086 (8)	0.094 (3)
H24A	−0.0272	0.8791	0.4711	0.140*
H24B	0.1811	0.8019	0.5006	0.140*
H24C	0.0202	0.7860	0.5894	0.140*
C25	0.2180 (17)	0.5849 (10)	0.4774 (10)	0.104 (4)
H25A	0.2351	0.5309	0.4253	0.156*
H25B	0.2182	0.5404	0.5557	0.156*
H25C	0.3197	0.6252	0.4693	0.156*
O26	−0.0092 (10)	0.7404 (5)	0.3172 (5)	0.0747 (17)

	U11	U22	U33	U12	U13	U23
C1	0.038 (3)	0.034 (3)	0.028 (3)	−0.015 (2)	−0.004 (2)	−0.008 (2)
C2	0.040 (3)	0.033 (3)	0.027 (3)	−0.016 (2)	−0.003 (2)	−0.006 (2)
C3	0.045 (4)	0.040 (4)	0.053 (4)	−0.019 (3)	0.003 (3)	−0.009 (3)
C4	0.065 (5)	0.036 (3)	0.055 (4)	−0.024 (3)	0.014 (3)	−0.006 (3)
C5	0.066 (5)	0.033 (3)	0.057 (4)	−0.013 (3)	0.004 (4)	−0.006 (3)
C6	0.051 (4)	0.033 (3)	0.038 (3)	−0.011 (3)	0.002 (3)	−0.008 (3)
N7	0.081 (5)	0.046 (4)	0.109 (6)	−0.033 (4)	0.030 (5)	−0.011 (4)
O8	0.115 (6)	0.048 (4)	0.140 (7)	−0.034 (4)	0.046 (5)	0.007 (4)
O9	0.081 (5)	0.072 (4)	0.156 (7)	−0.041 (4)	0.047 (5)	−0.016 (4)
C10	0.029 (3)	0.038 (3)	0.034 (3)	−0.012 (2)	−0.002 (2)	−0.007 (2)
N11	0.031 (2)	0.028 (2)	0.040 (3)	−0.011 (2)	−0.003 (2)	−0.003 (2)
C12	0.035 (7)	0.030 (7)	0.026 (8)	−0.010 (5)	−0.002 (7)	−0.008 (7)
C12A	0.031 (7)	0.033 (7)	0.034 (9)	−0.008 (5)	−0.003 (7)	−0.011 (7)
C13	0.034 (3)	0.038 (3)	0.050 (4)	−0.011 (3)	−0.003 (3)	−0.008 (3)
C14	0.040 (4)	0.040 (4)	0.121 (8)	−0.002 (3)	0.001 (4)	−0.008 (4)
C15	0.053 (8)	0.028 (6)	0.064 (10)	0.003 (6)	−0.013 (7)	−0.023 (6)
C16	0.050 (4)	0.036 (4)	0.093 (6)	−0.017 (3)	0.004 (4)	−0.021 (4)
C17	0.039 (6)	0.032 (6)	0.027 (7)	−0.010 (5)	0.001 (5)	−0.013 (5)
N18	0.032 (3)	0.042 (3)	0.039 (3)	−0.015 (2)	0.001 (2)	−0.009 (2)
V19	0.0284 (5)	0.0349 (6)	0.0256 (5)	−0.0116 (4)	−0.0012 (4)	−0.0062 (4)
O20	0.061 (3)	0.053 (3)	0.028 (2)	−0.007 (2)	−0.009 (2)	−0.005 (2)
O21	0.029 (2)	0.041 (2)	0.031 (2)	−0.0135 (17)	−0.0036 (16)	−0.0099 (17)
O22	0.042 (2)	0.033 (2)	0.037 (2)	−0.0149 (18)	0.0058 (18)	−0.0062 (17)
S23	0.0761 (14)	0.0722 (14)	0.0477 (11)	−0.0224 (11)	0.0021 (10)	−0.0052 (10)
C24	0.125 (9)	0.093 (7)	0.062 (6)	−0.005 (6)	−0.013 (6)	−0.038 (5)
C25	0.121 (10)	0.086 (7)	0.080 (7)	0.006 (7)	0.012 (7)	0.003 (6)
O26	0.114 (5)	0.066 (4)	0.043 (3)	−0.014 (3)	0.001 (3)	−0.020 (3)

C1—O22	1.323 (7)	C15—C16	1.564 (16)
C1—C6	1.405 (8)	C15—H15A	0.9700
C1—C2	1.410 (8)	C15—H15B	0.9700
C2—C3	1.397 (8)	C15A—C16	1.599 (16)
C2—C10	1.446 (8)	C15A—H15C	0.9700
C3—C4	1.375 (9)	C15A—H15D	0.9700
C3—H3A	0.9300	C16—C17A	1.567 (13)
C4—C5	1.377 (10)	C16—C17	1.570 (13)
C4—N7	1.468 (9)	C16—H16A	0.9700
C5—C6	1.373 (9)	C16—H16B	0.9700
C5—H5A	0.9300	C17—N18	1.503 (12)
C6—H6A	0.9300	C17—H17A	0.9800
N7—O9	1.215 (10)	C17A—N18	1.505 (12)
N7—O8	1.222 (9)	C17A—H17B	0.9800
C10—N11	1.284 (7)	N18—V19	2.109 (5)
C10—H10A	0.9300	N18—H18A	0.9000
N11—C12	1.487 (15)	N18—H18B	0.9000
N11—C12A	1.526 (15)	V19—O20	1.610 (4)
N11—V19	2.186 (5)	V19—O21i	1.663 (4)
C12—C13	1.507 (16)	V19—O22	1.929 (4)
C12—C17	1.529 (18)	V19—O21	2.372 (4)
C12—H12A	0.9800	O21—V19i	1.663 (4)
C12A—C17A	1.51 (2)	S23—O26	1.489 (6)
C12A—C13	1.534 (16)	S23—C24	1.744 (10)
C12A—H12B	0.9800	S23—C25	1.761 (11)
C13—C14	1.503 (9)	C24—H24A	0.9600
C13—H13A	0.9700	C24—H24B	0.9600
C13—H13B	0.9700	C24—H24C	0.9600
C14—C15	1.409 (15)	C25—H25A	0.9600
C14—C15A	1.439 (16)	C25—H25B	0.9600
C14—H14A	0.9700	C25—H25C	0.9600
C14—H14B	0.9700
O22—C1—C6	118.8 (5)	C14—C15A—H15D	110.0
O22—C1—C2	122.3 (5)	C16—C15A—H15D	110.0
C6—C1—C2	118.9 (5)	H15C—C15A—H15D	108.3
C3—C2—C1	119.3 (5)	C15—C16—C17A	116.3 (7)
C3—C2—C10	117.8 (6)	C15—C16—C17	105.1 (8)
C1—C2—C10	122.9 (5)	C17A—C16—C15A	104.9 (9)
C4—C3—C2	119.5 (6)	C17—C16—C15A	118.5 (8)
C4—C3—H3A	120.3	C15—C16—H16A	110.7
C2—C3—H3A	120.3	C17A—C16—H16A	77.7
C3—C4—C5	122.2 (6)	C17—C16—H16A	110.7
C3—C4—N7	118.8 (7)	C15A—C16—H16A	69.4
C5—C4—N7	119.0 (6)	C15—C16—H16B	110.7
C6—C5—C4	118.8 (6)	C17A—C16—H16B	126.2
C6—C5—H5A	120.6	C17—C16—H16B	110.7
C4—C5—H5A	120.6	C15A—C16—H16B	127.8
C5—C6—C1	121.1 (6)	H16A—C16—H16B	108.8
C5—C6—H6A	119.4	N18—C17—C12	106.1 (9)
C1—C6—H6A	119.4	N18—C17—C16	109.3 (8)
O9—N7—O8	124.1 (7)	C12—C17—C16	107.9 (9)
O9—N7—C4	118.3 (7)	N18—C17—H17A	111.1
O8—N7—C4	117.6 (8)	C12—C17—H17A	111.1
N11—C10—C2	124.0 (5)	C16—C17—H17A	111.1
N11—C10—H10A	118.0	N18—C17A—C12A	105.7 (10)
C2—C10—H10A	118.0	N18—C17A—C16	109.3 (8)
C10—N11—C12	120.6 (7)	C12A—C17A—C16	104.9 (10)
C10—N11—C12A	118.6 (7)	N18—C17A—H17B	112.2
C10—N11—V19	125.9 (4)	C12A—C17A—H17B	112.2
C12—N11—V19	112.6 (6)	C16—C17A—H17B	112.2
C12A—N11—V19	113.3 (6)	C17—N18—V19	113.2 (5)
N11—C12—C13	117.7 (10)	C17A—N18—V19	112.5 (5)
N11—C12—C17	102.5 (10)	C17—N18—H18A	108.9
C13—C12—C17	112.1 (11)	C17A—N18—H18A	77.3
N11—C12—H12A	108.1	V19—N18—H18A	108.9
C13—C12—H12A	108.1	C17—N18—H18B	108.9
C17—C12—H12A	108.1	C17A—N18—H18B	133.8
C17A—C12A—N11	103.9 (11)	V19—N18—H18B	108.9
C17A—C12A—C13	110.9 (11)	H18A—N18—H18B	107.8
N11—C12A—C13	113.7 (10)	O20—V19—O21i	106.7 (2)
C17A—C12A—H12B	109.4	O20—V19—O22	101.0 (2)
N11—C12A—H12B	109.4	O21i—V19—O22	99.26 (19)
C13—C12A—H12B	109.4	O20—V19—N18	94.0 (2)
C14—C13—C12	113.9 (7)	O21i—V19—N18	93.45 (19)
C14—C13—C12A	111.2 (7)	O22—V19—N18	156.55 (19)
C14—C13—H13A	108.8	O20—V19—N11	98.4 (2)
C12—C13—H13A	108.8	O21i—V19—N11	153.60 (19)
C12A—C13—H13A	86.8	O22—V19—N11	83.61 (18)
C14—C13—H13B	108.8	N18—V19—N11	76.42 (18)
C12—C13—H13B	108.8	O20—V19—O21	172.2 (2)
C12A—C13—H13B	129.9	O21i—V19—O21	77.86 (17)
H13A—C13—H13B	107.7	O22—V19—O21	84.18 (16)
C15—C14—C15A	46.2 (9)	N18—V19—O21	79.31 (17)
C15—C14—C13	118.0 (8)	N11—V19—O21	76.33 (16)
C15A—C14—C13	120.1 (9)	V19i—O21—V19	102.14 (17)
C15—C14—H14A	107.8	C1—O22—V19	129.1 (4)
C15A—C14—H14A	131.9	O26—S23—C24	106.2 (4)
C13—C14—H14A	107.8	O26—S23—C25	107.2 (5)
C15—C14—H14B	107.8	C24—S23—C25	98.3 (6)
C15A—C14—H14B	63.4	S23—C24—H24A	109.5
C13—C14—H14B	107.8	S23—C24—H24B	109.5
H14A—C14—H14B	107.2	H24A—C24—H24B	109.5
C14—C15—C16	112.3 (9)	S23—C24—H24C	109.5
C14—C15—H15A	109.1	H24A—C24—H24C	109.5
C16—C15—H15A	109.1	H24B—C24—H24C	109.5
C14—C15—H15B	109.1	S23—C25—H25A	109.5
C16—C15—H15B	109.1	S23—C25—H25B	109.5
H15A—C15—H15B	107.9	H25A—C25—H25B	109.5
C14—C15A—C16	108.7 (10)	S23—C25—H25C	109.5
C14—C15A—H15C	110.0	H25A—C25—H25C	109.5
C16—C15A—H15C	110.0	H25B—C25—H25C	109.5
O22—C1—C2—C3	−176.9 (5)	C15—C16—C17—N18	−179.6 (8)
C6—C1—C2—C3	0.2 (8)	C17A—C16—C17—N18	−64.4 (11)
O22—C1—C2—C10	4.5 (8)	C15A—C16—C17—N18	−137.2 (10)
C6—C1—C2—C10	−178.4 (5)	C15—C16—C17—C12	−64.7 (12)
C1—C2—C3—C4	−1.6 (9)	C17A—C16—C17—C12	50.5 (11)
C10—C2—C3—C4	177.1 (6)	C15A—C16—C17—C12	−22.3 (14)
C2—C3—C4—C5	−0.1 (11)	N11—C12A—C17A—N18	55.5 (12)
C2—C3—C4—N7	−179.9 (7)	C13—C12A—C17A—N18	178.1 (9)
C3—C4—C5—C6	3.0 (12)	N11—C12A—C17A—C16	170.9 (9)
N7—C4—C5—C6	−177.2 (7)	C13—C12A—C17A—C16	−66.5 (13)
C4—C5—C6—C1	−4.4 (11)	C15—C16—C17A—N18	141.3 (9)
O22—C1—C6—C5	−180.0 (6)	C17—C16—C17A—N18	64.3 (12)
C2—C1—C6—C5	2.8 (9)	C15A—C16—C17A—N18	−176.0 (9)
C3—C4—N7—O9	−13.0 (13)	C15—C16—C17A—C12A	28.3 (14)
C5—C4—N7—O9	167.2 (9)	C17—C16—C17A—C12A	−48.7 (12)
C3—C4—N7—O8	166.1 (8)	C15A—C16—C17A—C12A	71.0 (12)
C5—C4—N7—O8	−13.7 (13)	C12—C17—N18—C17A	−51.4 (11)
C3—C2—C10—N11	−165.8 (6)	C16—C17—N18—C17A	64.7 (11)
C1—C2—C10—N11	12.8 (9)	C12—C17—N18—V19	45.1 (10)
C2—C10—N11—C12	−167.3 (8)	C16—C17—N18—V19	161.1 (6)
C2—C10—N11—C12A	163.0 (8)	C12A—C17A—N18—C17	47.5 (11)
C2—C10—N11—V19	1.0 (8)	C16—C17A—N18—C17	−64.9 (12)
C10—N11—C12—C13	−20.5 (15)	C12A—C17A—N18—V19	−51.1 (11)
C12A—N11—C12—C13	73 (2)	C16—C17A—N18—V19	−163.6 (6)
V19—N11—C12—C13	169.7 (8)	C17—N18—V19—O20	82.6 (6)
C10—N11—C12—C17	−144.0 (8)	C17A—N18—V19—O20	120.2 (7)
C12A—N11—C12—C17	−50.9 (19)	C17—N18—V19—O21i	−170.4 (6)
V19—N11—C12—C17	46.2 (11)	C17A—N18—V19—O21i	−132.7 (7)
C10—N11—C12A—C17A	157.6 (8)	C17—N18—V19—O22	−47.4 (8)
C12—N11—C12A—C17A	56 (2)	C17A—N18—V19—O22	−9.8 (9)
V19—N11—C12A—C17A	−38.3 (12)	C17—N18—V19—N11	−15.1 (6)
C10—N11—C12A—C13	36.8 (14)	C17A—N18—V19—N11	22.6 (6)
C12—N11—C12A—C13	−65 (2)	C17—N18—V19—O21	−93.4 (6)
V19—N11—C12A—C13	−159.0 (8)	C17A—N18—V19—O21	−55.8 (7)
N11—C12—C13—C14	−162.4 (9)	C10—N11—V19—O20	80.1 (5)
C17—C12—C13—C14	−43.9 (13)	C12—N11—V19—O20	−110.8 (7)
N11—C12—C13—C12A	−73 (2)	C12A—N11—V19—O20	−82.7 (8)
C17—C12—C13—C12A	45.4 (18)	C10—N11—V19—O21i	−118.1 (6)
C17A—C12A—C13—C14	49.1 (14)	C12—N11—V19—O21i	51.0 (9)
N11—C12A—C13—C14	165.8 (9)	C12A—N11—V19—O21i	79.1 (9)
C17A—C12A—C13—C12	−52 (2)	C10—N11—V19—O22	−20.1 (5)
N11—C12A—C13—C12	64.4 (19)	C12—N11—V19—O22	149.0 (7)
C12—C13—C14—C15	39.7 (14)	C12A—N11—V19—O22	177.1 (7)
C12A—C13—C14—C15	12.1 (14)	C10—N11—V19—N18	172.2 (5)
C12—C13—C14—C15A	−13.6 (14)	C12—N11—V19—N18	−18.6 (7)
C12A—C13—C14—C15A	−41.2 (14)	C12A—N11—V19—N18	9.5 (7)
C15A—C14—C15—C16	57.2 (12)	C10—N11—V19—O21	−105.7 (5)
C13—C14—C15—C16	−48.9 (15)	C12—N11—V19—O21	63.5 (7)
C15—C14—C15A—C16	−53.4 (10)	C12A—N11—V19—O21	91.6 (7)
C13—C14—C15A—C16	47.8 (15)	O21i—V19—O21—V19i	0.000 (2)
C14—C15—C16—C17A	27.0 (15)	O22—V19—O21—V19i	100.8 (2)
C14—C15—C16—C17	60.4 (13)	N18—V19—O21—V19i	−95.9 (2)
C14—C15—C16—C15A	−55.7 (12)	N11—V19—O21—V19i	−174.4 (2)
C14—C15A—C16—C15	52.1 (11)	C6—C1—O22—V19	144.0 (4)
C14—C15A—C16—C17A	−60.9 (13)	C2—C1—O22—V19	−38.9 (7)
C14—C15A—C16—C17	−28.2 (15)	O20—V19—O22—C1	−58.2 (5)
N11—C12—C17—N18	−57.2 (11)	O21i—V19—O22—C1	−167.4 (5)
C13—C12—C17—N18	175.7 (9)	N18—V19—O22—C1	70.7 (7)
N11—C12—C17—C16	−174.2 (8)	N11—V19—O22—C1	39.1 (5)
C13—C12—C17—C16	58.7 (13)	O21—V19—O22—C1	116.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N18—H18A···O22i	0.90	2.29	3.069 (6)	145
N18—H18B···O26ii	0.90	2.16	2.913 (8)	140
C5—H5A···O26iii	0.93	2.57	3.494 (9)	171
C10—H10A···O21iv	0.93	2.49	3.167 (7)	130
C13—H13B···O21iv	0.97	2.55	3.392 (7)	145
C14—H14A···O26v	0.97	2.38	3.211 (11)	144
C15—H15B···O8vi	0.97	2.32	3.109 (17)	138

Table 1

Selected bond lengths (Å)

N11—V19	2.186 (5)
N18—V19	2.109 (5)
V19—O20	1.610 (4)
V19—O21i	1.663 (4)
V19—O22	1.929 (4)
V19—O21	2.372 (4)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N18—H18A⋯O22i	0.90	2.29	3.069 (6)	145
N18—H18B⋯O26ii	0.90	2.16	2.913 (8)	140
C5—H5A⋯O26iii	0.93	2.57	3.494 (9)	171
C10—H10A⋯O21iv	0.93	2.49	3.167 (7)	130
C13—H13B⋯O21iv	0.97	2.55	3.392 (7)	145
C14—H14A⋯O26v	0.97	2.38	3.211 (11)	144
C15—H15B⋯O8vi	0.97	2.32	3.109 (17)	138

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .