Oxido{N-[(2-oxido-1-naphthyl-κO)methyl-idene]asparaginato-κO,N}(1,10-phenanthroline-κN,N')vanadium(IV) N,N-dimethyl-formamide monosolvate.

The tridentate Schiff base ligand of the title complex, [V(C(15)H(12)N(2)O(4))O(C(12)H(8)N(2))]·C(3)H(7)NO, was derived from the condensation of 2-hy-droxy-1-naphthaldehyde and l-asparagine. The central V(IV) atom is six-coordinated by one oxide O atom, two N atoms from 1,10-phenanthroline and one N atom and two O atoms from the Schiff base ligand in a distorted octa-hedral geometry. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds connect mol-ecules into centrosymmetric dimers. The C atoms of the dimethyl-formamide solvent mol-ecule are disordered over two sites with site-occupancy factors of 0.732 (13) and 0.268 (13).

Related literature

For the insulin-mimetic properties of vanadium compounds, see: Diego et al. (2003 ▶); Kenji et al. (2000 ▶); Thompson & Orvig (2006 ▶). For related structures, see: Hoshina et al. (1998 ▶); Otieno et al. (1996 ▶).

Experimental

Crystal data

[V(C15H12N2O4)O(n class="CellLine">C12H8N2)]·C3H7NO

M = 604.51

Triclinic,

a = 10.357 (1) Å

b = 11.1021 (12) Å

c = 12.9119 (14) Å

α = 101.396 (2)°

β = 104.196 (2)°

γ = 91.010 (1)°

V = 1407.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.41 mm−1

T = 298 K

0.36 × 0.31 × 0.25 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.868, T max = 0.905

7387 measured reflections

4892 independent reflections

3123 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.216

S = 1.00

4892 reflections

411 parameters

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −0.40 e Å−3

Data collection: SMART (Bruker, 1996 ▶); cell refinement: SAINT (Bruker, 1996 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810030126/pv2309sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030126/pv2309Isup2.hkl

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

[V(C15H12N2O4)O(C12H8N2)]·C3H7NO	Z = 2
Mr = 604.51	F(000) = 626
Triclinic, P1	Dx = 1.426 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.357 (1) Å	Cell parameters from 1024 reflections
b = 11.1021 (12) Å	θ = 2.2–24.7°
c = 12.9119 (14) Å	µ = 0.41 mm−1
α = 101.396 (2)°	T = 298 K
β = 104.196 (2)°	Block, brown
γ = 91.010 (1)°	0.36 × 0.31 × 0.25 mm
V = 1407.5 (3) Å3

Bruker SMART 1000 CCD area-detector diffractometer	4892 independent reflections
Radiation source: fine-focus sealed tube	3123 reflections with I > 2σ(I)
graphite	Rint = 0.063
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→12
Tmin = 0.868, Tmax = 0.905	k = −13→13
7387 measured reflections	l = −13→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.216	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.13P)2] where P = (Fo2 + 2Fc2)/3
4892 reflections	(Δ/σ)max = 0.001
411 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
V1	0.21794 (8)	0.72939 (7)	0.12980 (6)	0.0417 (3)
N1	−0.0395 (4)	0.8528 (4)	0.4060 (3)	0.0547 (11)
H1A	−0.0235	0.8842	0.4747	0.066*
H1B	−0.0620	0.7755	0.3824	0.066*
N2	0.1611 (3)	0.9001 (3)	0.1906 (3)	0.0381 (8)
N3	0.2777 (3)	0.5734 (3)	0.0261 (3)	0.0402 (9)
N4	0.2988 (4)	0.8051 (3)	−0.0030 (3)	0.0435 (9)
N5	0.0667 (5)	0.5958 (5)	0.6803 (4)	0.0717 (13)
O1	0.0481 (3)	0.7362 (3)	0.0169 (3)	0.0495 (8)
O2	−0.1224 (3)	0.8505 (3)	−0.0363 (3)	0.0579 (9)
O3	0.0023 (4)	1.0347 (3)	0.3643 (3)	0.0595 (10)
O4	0.4011 (3)	0.7907 (3)	0.2145 (2)	0.0446 (8)
O5	0.1758 (3)	0.6444 (3)	0.2031 (3)	0.0547 (9)
O6	0.1289 (5)	0.4015 (4)	0.6468 (5)	0.1162 (19)
C1	−0.0249 (5)	0.8286 (4)	0.0315 (4)	0.0453 (11)
C2	0.0166 (4)	0.9110 (4)	0.1475 (3)	0.0392 (10)
H2	−0.0025	0.9968	0.1456	0.047*
C3	−0.0627 (5)	0.8583 (4)	0.2161 (4)	0.0459 (11)
H3A	−0.1572	0.8630	0.1844	0.055*
H3B	−0.0462	0.7720	0.2120	0.055*
C4	−0.0294 (4)	0.9237 (4)	0.3364 (4)	0.0438 (11)
C5	0.2340 (4)	0.9935 (4)	0.2540 (4)	0.0384 (10)
H5	0.1917	1.0660	0.2675	0.046*
C6	0.3739 (4)	0.9979 (4)	0.3061 (3)	0.0393 (10)
C7	0.4499 (4)	0.8934 (4)	0.2841 (3)	0.0390 (10)
C8	0.5882 (5)	0.9024 (4)	0.3411 (4)	0.0466 (11)
H8	0.6386	0.8353	0.3277	0.056*
C9	0.6482 (5)	1.0049 (5)	0.4137 (4)	0.0494 (12)
H9	0.7383	1.0060	0.4487	0.059*
C10	0.5767 (5)	1.1125 (4)	0.4385 (4)	0.0447 (11)
C11	0.4386 (5)	1.1087 (4)	0.3848 (4)	0.0431 (11)
C12	0.3706 (5)	1.2158 (4)	0.4134 (4)	0.0549 (13)
H12	0.2802	1.2173	0.3804	0.066*
C13	0.4364 (6)	1.3169 (5)	0.4890 (4)	0.0613 (14)
H13	0.3892	1.3854	0.5061	0.074*
C14	0.5722 (6)	1.3197 (5)	0.5408 (4)	0.0623 (14)
H14	0.6152	1.3894	0.5910	0.075*
C15	0.6402 (5)	1.2186 (5)	0.5165 (4)	0.0546 (13)
H15	0.7301	1.2190	0.5517	0.065*
C16	0.2636 (5)	0.4573 (4)	0.0400 (4)	0.0464 (11)
H16	0.2234	0.4435	0.0940	0.056*
C17	0.3071 (5)	0.3567 (4)	−0.0233 (4)	0.0538 (13)
H17	0.2967	0.2778	−0.0109	0.065*
C18	0.3653 (5)	0.3757 (5)	−0.1039 (4)	0.0540 (13)
H18	0.3962	0.3096	−0.1453	0.065*
C19	0.3785 (4)	0.4939 (4)	−0.1242 (4)	0.0472 (12)
C20	0.3325 (4)	0.5912 (4)	−0.0556 (4)	0.0416 (11)
C21	0.3453 (4)	0.7150 (4)	−0.0716 (4)	0.0424 (11)
C22	0.4021 (5)	0.7404 (5)	−0.1544 (4)	0.0532 (12)
C23	0.4084 (5)	0.8629 (5)	−0.1670 (4)	0.0618 (14)
H23	0.4442	0.8831	−0.2212	0.074*
C24	0.3612 (5)	0.9528 (5)	−0.0986 (4)	0.0632 (14)
H24	0.3659	1.0345	−0.1055	0.076*
C25	0.3058 (5)	0.9198 (4)	−0.0182 (4)	0.0516 (12)
H25	0.2725	0.9811	0.0264	0.062*
C26	0.4361 (5)	0.5229 (5)	−0.2071 (4)	0.0609 (14)
H26	0.4671	0.4599	−0.2518	0.073*
C27	0.4466 (5)	0.6385 (6)	−0.2220 (4)	0.0629 (15)
H27	0.4836	0.6534	−0.2775	0.076*
C28	0.0719 (10)	0.4856 (9)	0.7005 (9)	0.078 (3)	0.732 (13)
H28	0.0342	0.4672	0.7543	0.094*	0.732 (13)
C29	0.1211 (12)	0.6333 (11)	0.5983 (8)	0.102 (4)	0.732 (13)
H29A	0.1869	0.5782	0.5812	0.153*	0.732 (13)
H29B	0.1620	0.7155	0.6253	0.153*	0.732 (13)
H29C	0.0508	0.6313	0.5336	0.153*	0.732 (13)
C30	0.0016 (13)	0.6932 (11)	0.7444 (10)	0.116 (5)	0.732 (13)
H30A	−0.0315	0.6592	0.7965	0.174*	0.732 (13)
H30B	−0.0711	0.7220	0.6956	0.174*	0.732 (13)
H30C	0.0659	0.7608	0.7822	0.174*	0.732 (13)
C28'	0.140 (3)	0.508 (2)	0.619 (2)	0.085 (9)	0.268 (13)
H28'	0.1863	0.5244	0.5694	0.102*	0.268 (13)
C29'	−0.006 (3)	0.544 (3)	0.737 (3)	0.103 (11)	0.268 (13)
H29D	−0.0919	0.5131	0.6904	0.155*	0.268 (13)
H29E	−0.0175	0.6058	0.7977	0.155*	0.268 (13)
H29F	0.0401	0.4783	0.7646	0.155*	0.268 (13)
C30'	0.058 (3)	0.710 (3)	0.657 (3)	0.107 (11)	0.268 (13)
H30D	0.0192	0.7028	0.5802	0.161*	0.268 (13)
H30E	0.1457	0.7508	0.6764	0.161*	0.268 (13)
H30F	0.0031	0.7568	0.6977	0.161*	0.268 (13)

	U11	U22	U33	U12	U13	U23
V1	0.0477 (5)	0.0351 (5)	0.0436 (5)	0.0085 (3)	0.0187 (4)	0.0015 (3)
N1	0.077 (3)	0.040 (2)	0.047 (2)	0.008 (2)	0.021 (2)	0.002 (2)
N2	0.037 (2)	0.040 (2)	0.0375 (19)	0.0059 (16)	0.0129 (16)	0.0021 (17)
N3	0.038 (2)	0.037 (2)	0.046 (2)	0.0058 (15)	0.0151 (17)	0.0051 (17)
N4	0.046 (2)	0.040 (2)	0.046 (2)	0.0086 (16)	0.0131 (18)	0.0085 (18)
N5	0.083 (4)	0.059 (3)	0.072 (3)	0.007 (3)	0.015 (3)	0.017 (3)
O1	0.046 (2)	0.0448 (18)	0.0514 (18)	0.0068 (14)	0.0150 (15)	−0.0074 (16)
O2	0.051 (2)	0.066 (2)	0.0485 (19)	0.0130 (17)	0.0027 (17)	0.0049 (18)
O3	0.085 (3)	0.042 (2)	0.054 (2)	0.0017 (17)	0.0326 (19)	−0.0018 (17)
O4	0.0460 (19)	0.0415 (18)	0.0442 (17)	0.0115 (14)	0.0158 (15)	−0.0021 (15)
O5	0.066 (2)	0.0460 (19)	0.056 (2)	0.0083 (15)	0.0253 (18)	0.0080 (16)
O6	0.129 (5)	0.050 (3)	0.145 (5)	0.005 (3)	−0.002 (4)	0.009 (3)
C1	0.050 (3)	0.042 (3)	0.046 (3)	0.002 (2)	0.018 (2)	0.006 (2)
C2	0.037 (3)	0.038 (2)	0.043 (2)	0.0082 (18)	0.013 (2)	0.004 (2)
C3	0.047 (3)	0.046 (3)	0.046 (3)	0.006 (2)	0.019 (2)	0.003 (2)
C4	0.044 (3)	0.045 (3)	0.042 (3)	0.010 (2)	0.018 (2)	0.000 (2)
C5	0.044 (3)	0.033 (2)	0.045 (2)	0.0075 (19)	0.022 (2)	0.009 (2)
C6	0.042 (3)	0.040 (2)	0.039 (2)	0.0059 (19)	0.015 (2)	0.011 (2)
C7	0.042 (3)	0.044 (3)	0.036 (2)	0.0063 (19)	0.017 (2)	0.010 (2)
C8	0.046 (3)	0.051 (3)	0.045 (3)	0.012 (2)	0.016 (2)	0.009 (2)
C9	0.045 (3)	0.057 (3)	0.048 (3)	0.010 (2)	0.015 (2)	0.014 (3)
C10	0.046 (3)	0.049 (3)	0.042 (2)	−0.002 (2)	0.016 (2)	0.011 (2)
C11	0.048 (3)	0.041 (3)	0.043 (2)	0.003 (2)	0.018 (2)	0.006 (2)
C12	0.058 (3)	0.045 (3)	0.054 (3)	0.004 (2)	0.009 (3)	−0.002 (2)
C13	0.074 (4)	0.039 (3)	0.065 (3)	0.001 (2)	0.017 (3)	−0.002 (3)
C14	0.071 (4)	0.051 (3)	0.057 (3)	−0.013 (3)	0.013 (3)	−0.004 (3)
C15	0.054 (3)	0.055 (3)	0.051 (3)	−0.009 (2)	0.012 (2)	0.005 (3)
C16	0.046 (3)	0.034 (2)	0.058 (3)	0.0005 (19)	0.015 (2)	0.003 (2)
C17	0.048 (3)	0.038 (3)	0.065 (3)	0.001 (2)	0.007 (3)	−0.004 (2)
C18	0.049 (3)	0.049 (3)	0.053 (3)	0.010 (2)	0.009 (2)	−0.013 (2)
C19	0.040 (3)	0.052 (3)	0.042 (3)	0.008 (2)	0.008 (2)	−0.005 (2)
C20	0.039 (3)	0.044 (3)	0.039 (2)	0.008 (2)	0.010 (2)	0.002 (2)
C21	0.040 (3)	0.048 (3)	0.038 (2)	0.008 (2)	0.008 (2)	0.008 (2)
C22	0.051 (3)	0.066 (3)	0.045 (3)	0.009 (2)	0.015 (2)	0.012 (3)
C23	0.068 (4)	0.075 (4)	0.053 (3)	0.005 (3)	0.024 (3)	0.027 (3)
C24	0.073 (4)	0.059 (3)	0.067 (3)	0.010 (3)	0.023 (3)	0.028 (3)
C25	0.055 (3)	0.044 (3)	0.058 (3)	0.008 (2)	0.014 (3)	0.013 (2)
C26	0.056 (3)	0.073 (4)	0.048 (3)	0.015 (3)	0.017 (3)	−0.005 (3)
C27	0.064 (4)	0.083 (4)	0.045 (3)	0.011 (3)	0.025 (3)	0.006 (3)
C28	0.075 (7)	0.063 (6)	0.091 (7)	−0.004 (5)	0.009 (5)	0.022 (6)
C29	0.131 (10)	0.096 (9)	0.083 (7)	0.000 (7)	0.017 (7)	0.043 (7)
C30	0.141 (10)	0.096 (8)	0.099 (8)	0.062 (7)	0.021 (7)	0.001 (7)
C28'	0.10 (2)	0.065 (17)	0.095 (19)	0.000 (13)	0.022 (16)	0.020 (15)
C29'	0.11 (3)	0.10 (2)	0.11 (2)	0.001 (19)	0.04 (2)	0.017 (19)
C30'	0.11 (2)	0.09 (2)	0.12 (3)	0.012 (17)	0.02 (2)	0.02 (2)

V1—O5	1.587 (3)	C10—C11	1.424 (6)
V1—O4	1.975 (3)	C11—C12	1.424 (7)
V1—O1	2.004 (3)	C12—C13	1.375 (7)
V1—N2	2.057 (3)	C12—H12	0.9300
V1—N3	2.168 (3)	C13—C14	1.398 (7)
V1—N4	2.366 (4)	C13—H13	0.9300
N1—C4	1.326 (6)	C14—C15	1.361 (7)
N1—H1A	0.8600	C14—H14	0.9300
N1—H1B	0.8600	C15—H15	0.9300
N2—C5	1.284 (5)	C16—C17	1.399 (6)
N2—C2	1.480 (5)	C16—H16	0.9300
N3—C16	1.346 (5)	C17—C18	1.370 (7)
N3—C20	1.359 (5)	C17—H17	0.9300
N4—C25	1.329 (6)	C18—C19	1.398 (7)
N4—C21	1.376 (6)	C18—H18	0.9300
N5—C28	1.299 (10)	C19—C20	1.423 (6)
N5—C30'	1.36 (3)	C19—C26	1.432 (7)
N5—C29'	1.36 (3)	C20—C21	1.438 (6)
N5—C29	1.439 (11)	C21—C22	1.410 (6)
N5—C28'	1.48 (3)	C22—C23	1.403 (7)
N5—C30	1.503 (11)	C22—C27	1.443 (7)
O1—C1	1.297 (5)	C23—C24	1.377 (7)
O2—C1	1.226 (6)	C23—H23	0.9300
O3—C4	1.228 (5)	C24—C25	1.406 (7)
O4—C7	1.310 (5)	C24—H24	0.9300
O6—C28	1.290 (12)	C25—H25	0.9300
O6—C28'	1.31 (3)	C26—C27	1.342 (8)
C1—C2	1.547 (6)	C26—H26	0.9300
C2—C3	1.531 (6)	C27—H27	0.9300
C2—H2	0.9800	C28—H28	0.9300
C3—C4	1.530 (6)	C29—H29A	0.9600
C3—H3A	0.9700	C29—H29B	0.9600
C3—H3B	0.9700	C29—H29C	0.9600
C5—C6	1.436 (6)	C30—H30A	0.9600
C5—H5	0.9300	C30—H30B	0.9600
C6—C7	1.435 (6)	C30—H30C	0.9600
C6—C11	1.462 (6)	C28'—H28'	0.9300
C7—C8	1.432 (6)	C29'—H29D	0.9600
C8—C9	1.352 (6)	C29'—H29E	0.9600
C8—H8	0.9300	C29'—H29F	0.9600
C9—C10	1.440 (7)	C30'—H30D	0.9600
C9—H9	0.9300	C30'—H30E	0.9600
C10—C15	1.419 (6)	C30'—H30F	0.9600
O5—V1—O4	101.87 (16)	C15—C10—C11	120.5 (4)
O5—V1—O1	103.57 (16)	C15—C10—C9	121.3 (5)
O4—V1—O1	153.16 (14)	C11—C10—C9	118.2 (4)
O5—V1—N2	103.66 (15)	C10—C11—C12	116.6 (4)
O4—V1—N2	86.43 (13)	C10—C11—C6	119.8 (4)
O1—V1—N2	79.44 (13)	C12—C11—C6	123.6 (4)
O5—V1—N3	91.99 (15)	C13—C12—C11	121.0 (5)
O4—V1—N3	95.45 (12)	C13—C12—H12	119.5
O1—V1—N3	92.06 (13)	C11—C12—H12	119.5
N2—V1—N3	163.53 (14)	C12—C13—C14	121.9 (5)
O5—V1—N4	164.43 (15)	C12—C13—H13	119.1
O4—V1—N4	79.26 (13)	C14—C13—H13	119.1
O1—V1—N4	78.54 (13)	C15—C14—C13	118.8 (5)
N2—V1—N4	91.91 (13)	C15—C14—H14	120.6
N3—V1—N4	72.46 (13)	C13—C14—H14	120.6
C4—N1—H1A	120.0	C14—C15—C10	121.3 (5)
C4—N1—H1B	120.0	C14—C15—H15	119.4
H1A—N1—H1B	120.0	C10—C15—H15	119.4
C5—N2—C2	119.5 (4)	N3—C16—C17	122.6 (4)
C5—N2—V1	128.8 (3)	N3—C16—H16	118.7
C2—N2—V1	111.7 (2)	C17—C16—H16	118.7
C16—N3—C20	117.8 (4)	C18—C17—C16	119.3 (5)
C16—N3—V1	122.2 (3)	C18—C17—H17	120.4
C20—N3—V1	120.0 (3)	C16—C17—H17	120.4
C25—N4—C21	117.7 (4)	C17—C18—C19	120.5 (4)
C25—N4—V1	129.1 (3)	C17—C18—H18	119.8
C21—N4—V1	113.2 (3)	C19—C18—H18	119.8
C28—N5—C30'	178.4 (15)	C18—C19—C20	116.8 (4)
C28—N5—C29'	52.5 (14)	C18—C19—C26	124.7 (4)
C30'—N5—C29'	127 (2)	C20—C19—C26	118.6 (5)
C28—N5—C29	123.9 (9)	N3—C20—C19	123.1 (4)
C30'—N5—C29	56.0 (15)	N3—C20—C21	117.7 (4)
C29'—N5—C29	166.6 (15)	C19—C20—C21	119.2 (4)
C28—N5—C28'	63.0 (11)	N4—C21—C22	122.7 (4)
C30'—N5—C28'	117.0 (19)	N4—C21—C20	116.5 (4)
C29'—N5—C28'	114.5 (18)	C22—C21—C20	120.8 (4)
C29—N5—C28'	61.0 (11)	C23—C22—C21	117.7 (5)
C28—N5—C30	120.2 (9)	C23—C22—C27	124.4 (5)
C30'—N5—C30	59.9 (16)	C21—C22—C27	117.9 (5)
C29'—N5—C30	69.4 (15)	C24—C23—C22	119.6 (5)
C29—N5—C30	115.9 (9)	C24—C23—H23	120.2
C28'—N5—C30	175.2 (12)	C22—C23—H23	120.2
C1—O1—V1	119.2 (3)	C23—C24—C25	119.2 (5)
C7—O4—V1	132.7 (3)	C23—C24—H24	120.4
C28—O6—C28'	68.3 (13)	C25—C24—H24	120.4
O2—C1—O1	125.4 (4)	N4—C25—C24	123.1 (5)
O2—C1—C2	120.4 (4)	N4—C25—H25	118.4
O1—C1—C2	114.2 (4)	C24—C25—H25	118.4
N2—C2—C3	110.1 (4)	C27—C26—C19	121.8 (5)
N2—C2—C1	107.0 (3)	C27—C26—H26	119.1
C3—C2—C1	106.6 (3)	C19—C26—H26	119.1
N2—C2—H2	111.0	C26—C27—C22	121.7 (5)
C3—C2—H2	111.0	C26—C27—H27	119.1
C1—C2—H2	111.0	C22—C27—H27	119.1
C4—C3—C2	114.5 (4)	O6—C28—N5	120.8 (9)
C4—C3—H3A	108.6	O6—C28—H28	119.6
C2—C3—H3A	108.6	N5—C28—H28	119.6
C4—C3—H3B	108.6	N5—C29—H29A	109.5
C2—C3—H3B	108.6	N5—C29—H29B	109.5
H3A—C3—H3B	107.6	N5—C29—H29C	109.5
O3—C4—N1	123.5 (4)	N5—C30—H30A	109.5
O3—C4—C3	121.1 (4)	N5—C30—H30B	109.5
N1—C4—C3	115.4 (4)	N5—C30—H30C	109.5
N2—C5—C6	126.9 (4)	O6—C28'—N5	107.7 (19)
N2—C5—H5	116.6	O6—C28'—H28'	126.1
C6—C5—H5	116.6	N5—C28'—H28'	126.1
C7—C6—C5	120.7 (4)	N5—C29'—H29D	109.5
C7—C6—C11	119.7 (4)	N5—C29'—H29E	109.5
C5—C6—C11	119.6 (4)	H29D—C29'—H29E	109.5
O4—C7—C8	118.0 (4)	N5—C29'—H29F	109.5
O4—C7—C6	124.1 (4)	H29D—C29'—H29F	109.5
C8—C7—C6	117.9 (4)	H29E—C29'—H29F	109.5
C9—C8—C7	122.5 (4)	N5—C30'—H30D	109.5
C9—C8—H8	118.8	N5—C30'—H30E	109.5
C7—C8—H8	118.8	H30D—C30'—H30E	109.5
C8—C9—C10	121.9 (5)	N5—C30'—H30F	109.5
C8—C9—H9	119.1	H30D—C30'—H30F	109.5
C10—C9—H9	119.1	H30E—C30'—H30F	109.5
O5—V1—N2—C5	102.7 (4)	C7—C8—C9—C10	−0.1 (7)
O4—V1—N2—C5	1.4 (4)	C8—C9—C10—C15	178.7 (4)
O1—V1—N2—C5	−155.7 (4)	C8—C9—C10—C11	0.6 (7)
N3—V1—N2—C5	−95.8 (6)	C15—C10—C11—C12	0.4 (6)
N4—V1—N2—C5	−77.7 (4)	C9—C10—C11—C12	178.5 (4)
O5—V1—N2—C2	−80.4 (3)	C15—C10—C11—C6	−178.9 (4)
O4—V1—N2—C2	178.3 (3)	C9—C10—C11—C6	−0.7 (6)
O1—V1—N2—C2	21.2 (3)	C7—C6—C11—C10	0.4 (6)
N3—V1—N2—C2	81.1 (5)	C5—C6—C11—C10	178.7 (4)
N4—V1—N2—C2	99.2 (3)	C7—C6—C11—C12	−178.7 (4)
O5—V1—N3—C16	2.5 (4)	C5—C6—C11—C12	−0.5 (6)
O4—V1—N3—C16	104.7 (3)	C10—C11—C12—C13	0.1 (7)
O1—V1—N3—C16	−101.1 (4)	C6—C11—C12—C13	179.3 (4)
N2—V1—N3—C16	−159.5 (4)	C11—C12—C13—C14	0.1 (8)
N4—V1—N3—C16	−178.4 (4)	C12—C13—C14—C15	−0.8 (8)
O5—V1—N3—C20	−176.8 (3)	C13—C14—C15—C10	1.3 (7)
O4—V1—N3—C20	−74.7 (3)	C11—C10—C15—C14	−1.1 (7)
O1—V1—N3—C20	79.5 (3)	C9—C10—C15—C14	−179.2 (5)
N2—V1—N3—C20	21.2 (7)	C20—N3—C16—C17	2.2 (7)
N4—V1—N3—C20	2.2 (3)	V1—N3—C16—C17	−177.2 (3)
O5—V1—N4—C25	−178.2 (6)	N3—C16—C17—C18	−0.7 (7)
O4—V1—N4—C25	−82.5 (4)	C16—C17—C18—C19	−1.4 (7)
O1—V1—N4—C25	82.3 (4)	C17—C18—C19—C20	1.7 (7)
N2—V1—N4—C25	3.5 (4)	C17—C18—C19—C26	−179.2 (4)
N3—V1—N4—C25	178.2 (4)	C16—N3—C20—C19	−1.8 (6)
O5—V1—N4—C21	1.1 (8)	V1—N3—C20—C19	177.6 (3)
O4—V1—N4—C21	96.8 (3)	C16—N3—C20—C21	178.9 (4)
O1—V1—N4—C21	−98.4 (3)	V1—N3—C20—C21	−1.7 (5)
N2—V1—N4—C21	−177.2 (3)	C18—C19—C20—N3	−0.1 (7)
N3—V1—N4—C21	−2.5 (3)	C26—C19—C20—N3	−179.3 (4)
O5—V1—O1—C1	96.2 (3)	C18—C19—C20—C21	179.1 (4)
O4—V1—O1—C1	−64.9 (4)	C26—C19—C20—C21	0.0 (7)
N2—V1—O1—C1	−5.5 (3)	C25—N4—C21—C22	1.6 (6)
N3—V1—O1—C1	−171.3 (3)	V1—N4—C21—C22	−177.8 (3)
N4—V1—O1—C1	−99.6 (3)	C25—N4—C21—C20	−178.0 (4)
O5—V1—O4—C7	−97.9 (4)	V1—N4—C21—C20	2.6 (5)
O1—V1—O4—C7	63.3 (5)	N3—C20—C21—N4	−0.8 (6)
N2—V1—O4—C7	5.3 (4)	C19—C20—C21—N4	179.9 (4)
N3—V1—O4—C7	168.9 (4)	N3—C20—C21—C22	179.6 (4)
N4—V1—O4—C7	98.0 (4)	C19—C20—C21—C22	0.3 (7)
V1—O1—C1—O2	171.5 (4)	N4—C21—C22—C23	−1.1 (7)
V1—O1—C1—C2	−11.2 (5)	C20—C21—C22—C23	178.5 (4)
C5—N2—C2—C3	−98.3 (4)	N4—C21—C22—C27	−179.6 (4)
V1—N2—C2—C3	84.5 (3)	C20—C21—C22—C27	0.0 (7)
C5—N2—C2—C1	146.2 (4)	C21—C22—C23—C24	0.7 (8)
V1—N2—C2—C1	−31.0 (4)	C27—C22—C23—C24	179.1 (5)
O2—C1—C2—N2	−155.0 (4)	C22—C23—C24—C25	−0.9 (8)
O1—C1—C2—N2	27.5 (5)	C21—N4—C25—C24	−1.7 (7)
O2—C1—C2—C3	87.2 (5)	V1—N4—C25—C24	177.6 (4)
O1—C1—C2—C3	−90.3 (4)	C23—C24—C25—N4	1.4 (8)
N2—C2—C3—C4	61.0 (5)	C18—C19—C26—C27	−179.6 (5)
C1—C2—C3—C4	176.7 (4)	C20—C19—C26—C27	−0.5 (7)
C2—C3—C4—O3	33.3 (6)	C19—C26—C27—C22	0.9 (8)
C2—C3—C4—N1	−147.8 (4)	C23—C22—C27—C26	−178.9 (5)
C2—N2—C5—C6	177.5 (4)	C21—C22—C27—C26	−0.6 (8)
V1—N2—C5—C6	−5.9 (6)	C28'—O6—C28—N5	3.5 (14)
N2—C5—C6—C7	4.5 (6)	C29'—N5—C28—O6	165 (2)
N2—C5—C6—C11	−173.8 (4)	C29—N5—C28—O6	0.5 (13)
V1—O4—C7—C8	172.9 (3)	C28'—N5—C28—O6	−3.2 (13)
V1—O4—C7—C6	−7.7 (6)	C30—N5—C28—O6	−179.2 (8)
C5—C6—C7—O4	2.3 (6)	C28—O6—C28'—N5	−2.8 (11)
C11—C6—C7—O4	−179.4 (4)	C28—N5—C28'—O6	2.9 (11)
C5—C6—C7—C8	−178.3 (4)	C30'—N5—C28'—O6	−175.3 (18)
C11—C6—C7—C8	0.0 (6)	C29'—N5—C28'—O6	−8(2)
O4—C7—C8—C9	179.3 (4)	C29—N5—C28'—O6	−174 (2)
C6—C7—C8—C9	−0.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3i	0.86	2.05	2.909 (5)	175
N1—H1B···O6ii	0.86	2.00	2.852 (6)	169
C16—H16···O5	0.93	2.52	2.975 (5)	111
C29—H29A···O6	0.96	2.41	2.764 (11)	102
C29—H29C···O6ii	0.96	2.56	3.511 (12)	173
C25—H25···O2iii	0.93	2.46	3.275 (6)	147
C17—H17···O2iv	0.93	2.54	3.288 (6)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3i	0.86	2.05	2.909 (5)	175
N1—H1B⋯O6ii	0.86	2.00	2.852 (6)	169

Symmetry codes: (i) ; (ii) .