metal-organic compounds
κ4O,N,N′,O′}oxidovanadium(IV) methanol monosolvate
of {2,2′-[ethylenebis(nitrilomethanylylidene)]diphenolato-aSchool of Chemistry, The University of Nottingham, University Park, Nottingham NG7 2RD, England
*Correspondence e-mail: a.j.blake@nottingham.ac.uk
Two independent molecules of the title solvated complex, [V(C16H14N2O2)O]·CH3OH, also known as [N,N′-bis(salicylidene)ethylenediamine]oxidovanadium(IV) or vanadyl salen, crystallize in the Each disordered methanol solvent molecule [occupancy ratios 0.678 (4):0.322 (4) and 0.750 (5):0.250 (5)] is linked to a [N,N′-bis(salicylidene)ethylenediamine]oxidovanadium(IV) molecule by an O—H⋯O hydrogen bond and to others by C—H⋯O hydrogen bonds. The resulting extended structure consists of a bilayer of molecules parallel to the ab plane. Despite the fact that solvates are common in complexes derived from substituted analogues of the N,N′-bis(salicylidene)ethylenediamine ligand, the title solvate is the first one of [N,N′-bis(salicylidene)ethylenediamine]oxidovanadium(IV) to be structurally characterized. The two vanadyl species have very similar internal geometries, which are best characterized as distorted square-based pyramidal with the vanadium atom displaced from the N2O2 basal plane by 0.5966 (9) Å in the direction of the doubly-bonded oxide ligand.
Keywords: crystal structure; oxidovanadium(IV); 2,2′-[ethylenebis(nitrilomethanylylidene)]diphenolate; N,N′-bis(salicylidene)ethylenediamine; hydrogen bonding.
CCDC reference: 1030592
1. Related literature
The literature reports three structure determinations on the unsolvated title complex, also known as [N,N′-bis(salicylidene)ethylenediamine]oxidovanadium(IV). The first was in the monoclinic P21/c by Riley et al. (1986), the second by Li et al. (2004) in the triclinic P and the third in the monoclinic P21 (Wang et al., 2008). All three determinations were carried out at ambient temperature. According to the Cambridge Structural Database (Groom & Allen, 2014) no solvates of [N,N′-bis(salicylidene)ethylenediamine]oxidovanadium(IV) have been reported previously, although these are common for substituted analogues of the N,N′-bis(salicylidene)ethylenediamine ligand.
2. Experimental
2.1. Crystal data
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Data collection: CrysAlis PRO (Agilent, 2013); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2.
Supporting information
CCDC reference: 1030592
10.1107/S1600536814023332/gg2143sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814023332/gg2143Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814023332/gg2143Isup3.cdx
Crystals of the title complex were obtained by slow cooling of a methanolic solution of {2,2'-[ethylenebis(nitrilomethylidyne)]diphenolato-κ4O,N,N',O'}oxidovanadium(IV).
With the exceptions of methyl groups (which were refined as rigid rotating groups) and OH groups (for which were idealized tetrahedral OH were refined as rigid rotating groups), H atoms were allowed to ride on their parent atoms with Uiso(H) = 1.5 × Ueq(C,O) for methyl and OH groups and 1.2 × Ueq(C) for others.
The O8–C34, O8A–C34A, O7–C33 and O7A–C33A distances were restrained to a target value of 1.43 (1) Å. SIMU and RIGU restraints (Sheldrick, 2008) were applied to the solvent molecules, and linked occupancies were used to stabilize the
of the MeOH solvent molecules.For the
determination, the classical Flack method was preferred over Parsons because the s.u. was lower.Data collection: CrysAlis PRO (Agilent, 2013); cell
CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).Fig. 1. One of the two independent solvated molecules in the asymmetric unit, with atom labels and 50% probability displacement ellipsoids for non-H atoms. Only one component of the disordered MeOH molecule is shown. |
[V(C16H14N2O2)O]·CH4O | Dx = 1.480 Mg m−3 |
Mr = 365.27 | Cu Kα radiation, λ = 1.54184 Å |
Orthorhombic, Pna21 | Cell parameters from 3840 reflections |
a = 12.9597 (4) Å | θ = 5.2–72.3° |
b = 8.8616 (2) Å | µ = 5.27 mm−1 |
c = 28.5426 (7) Å | T = 120 K |
V = 3277.92 (15) Å3 | Block, green |
Z = 8 | 0.31 × 0.14 × 0.05 mm |
F(000) = 1512 |
Agilent GV1000 diffractometer with an Atlas CCD detector | 4634 independent reflections |
Radiation source: Agilent GV1000 (Cu) X-ray Source | 4350 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.025 |
Detector resolution: 10.3271 pixels mm-1 | θmax = 74.4°, θmin = 5.2° |
ω scans | h = −15→15 |
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2013) | k = −10→6 |
Tmin = 0.480, Tmax = 0.959 | l = −33→34 |
7416 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.065P)2 + 1.252P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.105 | (Δ/σ)max = 0.02 |
S = 1.04 | Δρmax = 0.42 e Å−3 |
4634 reflections | Δρmin = −0.29 e Å−3 |
479 parameters | Absolute structure: Flack (1983), 1395 Friedel pairs |
32 restraints | Absolute structure parameter: 0.066 (9) |
Primary atom site location: structure-invariant direct methods |
[V(C16H14N2O2)O]·CH4O | V = 3277.92 (15) Å3 |
Mr = 365.27 | Z = 8 |
Orthorhombic, Pna21 | Cu Kα radiation |
a = 12.9597 (4) Å | µ = 5.27 mm−1 |
b = 8.8616 (2) Å | T = 120 K |
c = 28.5426 (7) Å | 0.31 × 0.14 × 0.05 mm |
Agilent GV1000 diffractometer with an Atlas CCD detector | 4634 independent reflections |
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2013) | 4350 reflections with I > 2σ(I) |
Tmin = 0.480, Tmax = 0.959 | Rint = 0.025 |
7416 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.105 | Δρmax = 0.42 e Å−3 |
S = 1.04 | Δρmin = −0.29 e Å−3 |
4634 reflections | Absolute structure: Flack (1983), 1395 Friedel pairs |
479 parameters | Absolute structure parameter: 0.066 (9) |
32 restraints |
Experimental. Absorption correction: CrysAlisPro version 1.171.36.32 (Agilent, 2013). Numerical absorption correction based on Gaussian integration over a multifaceted crystal model. |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
V1 | 0.33525 (3) | 1.13029 (4) | 0.50170 (2) | 0.02409 (8) | |
V2 | 0.57988 (3) | 0.36777 (4) | 0.18892 (2) | 0.02364 (8) | |
O1 | 0.24854 (12) | 0.95916 (19) | 0.49027 (6) | 0.0305 (4) | |
O2 | 0.41375 (12) | 1.06657 (19) | 0.44719 (6) | 0.0277 (4) | |
O3 | 0.41104 (12) | 1.1086 (2) | 0.54575 (6) | 0.0298 (4) | |
O4 | 0.49307 (12) | 0.53856 (17) | 0.20089 (6) | 0.0292 (4) | |
O5 | 0.65555 (12) | 0.39010 (19) | 0.14477 (6) | 0.0292 (4) | |
O6 | 0.65825 (12) | 0.4296 (2) | 0.24318 (6) | 0.0294 (4) | |
N2 | 0.35312 (15) | 1.3476 (2) | 0.47830 (7) | 0.0275 (4) | |
N4 | 0.59693 (16) | 0.1492 (2) | 0.21225 (7) | 0.0289 (5) | |
C12 | 0.49325 (19) | 1.1394 (3) | 0.42862 (7) | 0.0283 (6) | |
C14 | 0.42784 (18) | 1.3949 (3) | 0.45247 (8) | 0.0295 (5) | |
H14 | 0.4327 | 1.4981 | 0.4471 | 0.035* | |
C30 | 0.73712 (18) | 0.3563 (3) | 0.26195 (8) | 0.0306 (6) | |
C3 | 0.15814 (17) | 0.9193 (3) | 0.50810 (8) | 0.0280 (5) | |
C25 | 0.6714 (2) | 0.1024 (3) | 0.23826 (8) | 0.0322 (6) | |
H25 | 0.6761 | −0.0010 | 0.2435 | 0.039* | |
N1 | 0.20834 (14) | 1.2335 (2) | 0.53104 (7) | 0.0269 (4) | |
C26 | 0.8334 (2) | 0.1282 (3) | 0.28130 (9) | 0.0409 (7) | |
H26 | 0.8397 | 0.0237 | 0.2803 | 0.049* | |
N3 | 0.45275 (15) | 0.2651 (2) | 0.15943 (7) | 0.0278 (4) | |
C4 | 0.09719 (17) | 1.0158 (3) | 0.53631 (7) | 0.0273 (5) | |
C10 | 0.6518 (2) | 1.1282 (4) | 0.38350 (9) | 0.0423 (8) | |
H10 | 0.7005 | 1.0710 | 0.3674 | 0.051* | |
C8 | 0.5908 (2) | 1.3668 (3) | 0.40987 (8) | 0.0396 (7) | |
H8 | 0.5986 | 1.4710 | 0.4113 | 0.048* | |
C15 | 0.2266 (2) | 1.3957 (3) | 0.53910 (9) | 0.0326 (6) | |
H15A | 0.2729 | 1.4102 | 0.5654 | 0.039* | |
H15B | 0.1621 | 1.4470 | 0.5457 | 0.039* | |
C22 | 0.40338 (16) | 0.5789 (3) | 0.18283 (8) | 0.0273 (5) | |
C17 | 0.36417 (19) | 0.7228 (3) | 0.19338 (10) | 0.0352 (6) | |
H17 | 0.4014 | 0.7860 | 0.2132 | 0.042* | |
C24 | 0.74815 (18) | 0.1970 (3) | 0.26002 (8) | 0.0316 (6) | |
C13 | 0.12347 (18) | 1.1718 (3) | 0.54445 (8) | 0.0295 (5) | |
H13 | 0.0761 | 1.2316 | 0.5604 | 0.035* | |
C18 | 0.2719 (2) | 0.7725 (3) | 0.17509 (9) | 0.0390 (6) | |
H18 | 0.2478 | 0.8680 | 0.1830 | 0.047* | |
C1 | 0.0269 (2) | 0.7261 (3) | 0.51707 (9) | 0.0375 (6) | |
H1 | 0.0032 | 0.6295 | 0.5102 | 0.045* | |
C9 | 0.50432 (18) | 1.2990 (3) | 0.43126 (7) | 0.0301 (6) | |
C7 | 0.6641 (2) | 1.2817 (4) | 0.38686 (9) | 0.0451 (8) | |
H7 | 0.7215 | 1.3281 | 0.3737 | 0.054* | |
C20 | 0.34189 (17) | 0.4834 (3) | 0.15433 (7) | 0.0278 (5) | |
C28 | 0.8976 (2) | 0.3678 (4) | 0.30590 (9) | 0.0440 (8) | |
H28 | 0.9476 | 0.4251 | 0.3211 | 0.053* | |
C2 | 0.11882 (19) | 0.7752 (3) | 0.49797 (9) | 0.0331 (6) | |
H2 | 0.1554 | 0.7117 | 0.4780 | 0.040* | |
C23 | 0.36811 (17) | 0.3277 (3) | 0.14619 (8) | 0.0283 (5) | |
H23 | 0.3205 | 0.2683 | 0.1302 | 0.034* | |
C16 | 0.27463 (19) | 1.4566 (3) | 0.49437 (9) | 0.0333 (6) | |
H16A | 0.2220 | 1.4695 | 0.4705 | 0.040* | |
H16B | 0.3064 | 1.5539 | 0.5003 | 0.040* | |
C5 | 0.00379 (18) | 0.9625 (3) | 0.55506 (8) | 0.0323 (6) | |
H5 | −0.0355 | 1.0263 | 0.5738 | 0.039* | |
C21 | 0.24831 (18) | 0.5379 (3) | 0.13563 (8) | 0.0334 (6) | |
H21 | 0.2088 | 0.4753 | 0.1166 | 0.040* | |
C11 | 0.56715 (19) | 1.0573 (3) | 0.40398 (8) | 0.0344 (6) | |
H11 | 0.5598 | 0.9533 | 0.4011 | 0.041* | |
C19 | 0.21417 (19) | 0.6823 (3) | 0.14501 (9) | 0.0377 (6) | |
H19 | 0.1538 | 0.7186 | 0.1315 | 0.045* | |
C27 | 0.9082 (2) | 0.2117 (4) | 0.30372 (9) | 0.0508 (8) | |
H27 | 0.9650 | 0.1644 | 0.3172 | 0.061* | |
C6 | −0.03109 (19) | 0.8186 (3) | 0.54647 (9) | 0.0362 (6) | |
H6 | −0.0919 | 0.7839 | 0.5600 | 0.043* | |
C29 | 0.81364 (18) | 0.4385 (4) | 0.28575 (8) | 0.0360 (6) | |
H29 | 0.8076 | 0.5429 | 0.2880 | 0.043* | |
C31 | 0.51874 (19) | 0.0415 (3) | 0.19582 (9) | 0.0328 (6) | |
H31A | 0.4662 | 0.0279 | 0.2196 | 0.039* | |
H31B | 0.5505 | −0.0555 | 0.1896 | 0.039* | |
C32 | 0.4706 (2) | 0.1028 (3) | 0.15151 (9) | 0.0332 (6) | |
H32A | 0.5165 | 0.0879 | 0.1251 | 0.040* | |
H32B | 0.4059 | 0.0518 | 0.1451 | 0.040* | |
O8 | 0.3881 (3) | 0.7530 (4) | 0.41726 (11) | 0.0533 (9) | 0.678 (4) |
H8A | 0.3953 | 0.8354 | 0.4299 | 0.080* | 0.678 (4) |
O7 | 0.6257 (3) | 0.7431 (3) | 0.27352 (11) | 0.0573 (9) | 0.750 (5) |
H7A | 0.6295 | 0.6685 | 0.2566 | 0.086* | 0.750 (5) |
C33 | 0.5510 (3) | 0.7185 (6) | 0.30846 (13) | 0.0506 (11) | 0.750 (5) |
H33A | 0.4851 | 0.7011 | 0.2940 | 0.076* | 0.750 (5) |
H33B | 0.5469 | 0.8056 | 0.3284 | 0.076* | 0.750 (5) |
H33C | 0.5700 | 0.6320 | 0.3268 | 0.076* | 0.750 (5) |
C34 | 0.3009 (4) | 0.7570 (6) | 0.38743 (15) | 0.0614 (14) | 0.678 (4) |
H34A | 0.3138 | 0.6966 | 0.3602 | 0.092* | 0.678 (4) |
H34B | 0.2876 | 0.8593 | 0.3781 | 0.092* | 0.678 (4) |
H34C | 0.2419 | 0.7180 | 0.4038 | 0.092* | 0.678 (4) |
O7A | 0.5715 (10) | 0.7560 (9) | 0.2706 (2) | 0.068 (3) | 0.250 (5) |
H7AA | 0.5107 | 0.7627 | 0.2629 | 0.103* | 0.250 (5) |
C33A | 0.5784 (9) | 0.6910 (16) | 0.3163 (3) | 0.073 (4) | 0.250 (5) |
H33D | 0.6391 | 0.6293 | 0.3182 | 0.110* | 0.250 (5) |
H33E | 0.5185 | 0.6302 | 0.3221 | 0.110* | 0.250 (5) |
H33F | 0.5823 | 0.7700 | 0.3393 | 0.110* | 0.250 (5) |
C34A | 0.3143 (7) | 0.7847 (9) | 0.37978 (19) | 0.041 (2) | 0.322 (4) |
H34D | 0.3315 | 0.7086 | 0.3572 | 0.061* | 0.322 (4) |
H34E | 0.3511 | 0.8759 | 0.3726 | 0.061* | 0.322 (4) |
H34F | 0.2414 | 0.8038 | 0.3788 | 0.061* | 0.322 (4) |
O8A | 0.3422 (6) | 0.7342 (7) | 0.42510 (16) | 0.0481 (19) | 0.322 (4) |
H8AA | 0.3271 | 0.7990 | 0.4444 | 0.072* | 0.322 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
V1 | 0.02276 (15) | 0.02190 (17) | 0.02763 (14) | 0.00204 (14) | −0.00088 (14) | −0.00101 (14) |
V2 | 0.02314 (15) | 0.02248 (17) | 0.02531 (14) | −0.00205 (14) | 0.00061 (14) | −0.00063 (14) |
O1 | 0.0274 (7) | 0.0247 (8) | 0.0394 (8) | 0.0009 (6) | 0.0042 (7) | −0.0034 (7) |
O2 | 0.0263 (7) | 0.0274 (8) | 0.0295 (7) | −0.0023 (7) | 0.0018 (6) | −0.0025 (6) |
O3 | 0.0232 (7) | 0.0338 (9) | 0.0325 (7) | 0.0038 (7) | −0.0038 (6) | 0.0015 (7) |
O4 | 0.0276 (7) | 0.0246 (8) | 0.0355 (7) | −0.0019 (6) | −0.0030 (7) | −0.0032 (7) |
O5 | 0.0249 (7) | 0.0318 (8) | 0.0310 (7) | −0.0031 (7) | 0.0021 (6) | 0.0000 (7) |
O6 | 0.0282 (7) | 0.0312 (8) | 0.0289 (6) | −0.0007 (7) | −0.0021 (6) | −0.0023 (7) |
N2 | 0.0288 (8) | 0.0239 (9) | 0.0297 (8) | 0.0006 (8) | −0.0091 (8) | −0.0023 (8) |
N4 | 0.0326 (9) | 0.0250 (9) | 0.0290 (8) | 0.0013 (8) | 0.0067 (8) | 0.0004 (8) |
C12 | 0.0333 (11) | 0.0334 (12) | 0.0183 (8) | −0.0018 (10) | −0.0057 (9) | 0.0025 (8) |
C14 | 0.0329 (11) | 0.0300 (11) | 0.0255 (9) | −0.0055 (10) | −0.0071 (9) | 0.0028 (9) |
C30 | 0.0270 (10) | 0.0426 (13) | 0.0222 (8) | 0.0018 (10) | 0.0061 (9) | −0.0022 (9) |
C3 | 0.0259 (9) | 0.0266 (10) | 0.0316 (9) | 0.0010 (9) | −0.0035 (9) | 0.0032 (9) |
C25 | 0.0432 (12) | 0.0287 (11) | 0.0248 (9) | 0.0079 (10) | 0.0086 (10) | 0.0029 (9) |
N1 | 0.0230 (8) | 0.0278 (9) | 0.0301 (8) | 0.0034 (7) | −0.0022 (7) | −0.0059 (8) |
C26 | 0.0420 (13) | 0.0542 (16) | 0.0266 (10) | 0.0179 (12) | 0.0028 (11) | 0.0024 (11) |
N3 | 0.0285 (9) | 0.0256 (9) | 0.0294 (8) | −0.0043 (8) | 0.0036 (8) | −0.0056 (8) |
C4 | 0.0263 (10) | 0.0307 (11) | 0.0248 (8) | 0.0021 (9) | −0.0051 (8) | 0.0022 (9) |
C10 | 0.0376 (13) | 0.0658 (19) | 0.0234 (9) | 0.0038 (13) | 0.0046 (10) | 0.0017 (11) |
C8 | 0.0449 (14) | 0.0480 (15) | 0.0260 (10) | −0.0143 (12) | −0.0023 (10) | 0.0045 (10) |
C15 | 0.0321 (11) | 0.0289 (11) | 0.0368 (11) | 0.0081 (10) | −0.0023 (10) | −0.0079 (9) |
C22 | 0.0228 (9) | 0.0292 (11) | 0.0300 (9) | 0.0006 (9) | 0.0034 (9) | 0.0061 (9) |
C17 | 0.0319 (10) | 0.0290 (11) | 0.0447 (12) | −0.0012 (10) | 0.0053 (11) | 0.0022 (11) |
C24 | 0.0346 (11) | 0.0369 (12) | 0.0233 (8) | 0.0073 (11) | 0.0044 (9) | 0.0012 (10) |
C13 | 0.0254 (10) | 0.0372 (12) | 0.0257 (9) | 0.0077 (10) | −0.0029 (9) | −0.0041 (9) |
C18 | 0.0391 (12) | 0.0319 (12) | 0.0458 (12) | 0.0081 (11) | 0.0133 (11) | 0.0098 (11) |
C1 | 0.0357 (12) | 0.0302 (11) | 0.0468 (12) | −0.0025 (11) | −0.0094 (11) | 0.0112 (11) |
C9 | 0.0310 (10) | 0.0420 (13) | 0.0172 (8) | −0.0051 (11) | −0.0043 (9) | 0.0023 (9) |
C7 | 0.0394 (13) | 0.0687 (19) | 0.0272 (10) | −0.0097 (13) | 0.0092 (10) | 0.0072 (12) |
C20 | 0.0225 (9) | 0.0351 (12) | 0.0258 (9) | −0.0038 (9) | 0.0030 (8) | −0.0002 (9) |
C28 | 0.0322 (12) | 0.075 (2) | 0.0250 (10) | −0.0029 (13) | −0.0005 (10) | −0.0022 (11) |
C2 | 0.0306 (11) | 0.0276 (11) | 0.0411 (11) | −0.0002 (10) | −0.0026 (10) | 0.0023 (10) |
C23 | 0.0230 (9) | 0.0349 (12) | 0.0269 (9) | −0.0054 (10) | 0.0001 (8) | −0.0029 (9) |
C16 | 0.0349 (11) | 0.0237 (11) | 0.0412 (11) | 0.0045 (10) | −0.0115 (10) | −0.0012 (9) |
C5 | 0.0268 (10) | 0.0438 (14) | 0.0262 (9) | 0.0024 (10) | −0.0019 (9) | 0.0028 (10) |
C21 | 0.0265 (10) | 0.0468 (14) | 0.0269 (9) | −0.0018 (11) | 0.0017 (9) | 0.0081 (10) |
C11 | 0.0348 (11) | 0.0461 (14) | 0.0223 (8) | 0.0024 (11) | −0.0023 (9) | −0.0005 (10) |
C19 | 0.0292 (11) | 0.0481 (14) | 0.0358 (10) | 0.0045 (11) | 0.0040 (10) | 0.0134 (11) |
C27 | 0.0431 (13) | 0.079 (2) | 0.0301 (11) | 0.0202 (15) | −0.0037 (11) | 0.0057 (13) |
C6 | 0.0263 (10) | 0.0466 (14) | 0.0356 (10) | −0.0044 (11) | −0.0024 (10) | 0.0126 (11) |
C29 | 0.0291 (10) | 0.0553 (15) | 0.0238 (9) | −0.0055 (11) | 0.0001 (9) | −0.0019 (10) |
C31 | 0.0377 (11) | 0.0225 (11) | 0.0383 (11) | −0.0061 (9) | 0.0077 (10) | −0.0031 (10) |
C32 | 0.0340 (11) | 0.0263 (11) | 0.0394 (11) | −0.0039 (10) | 0.0084 (10) | −0.0086 (10) |
O8 | 0.0693 (19) | 0.0407 (16) | 0.0501 (15) | 0.0048 (15) | −0.0044 (16) | −0.0062 (14) |
O7 | 0.0792 (19) | 0.0308 (13) | 0.0618 (16) | −0.0094 (14) | 0.0178 (16) | −0.0105 (13) |
C33 | 0.055 (2) | 0.058 (2) | 0.0383 (16) | 0.006 (2) | −0.0047 (17) | −0.0122 (16) |
C34 | 0.086 (3) | 0.057 (3) | 0.0412 (19) | −0.025 (2) | −0.008 (2) | 0.0187 (19) |
O7A | 0.122 (8) | 0.028 (4) | 0.055 (4) | 0.017 (5) | −0.020 (4) | −0.016 (3) |
C33A | 0.043 (5) | 0.105 (9) | 0.071 (5) | 0.049 (5) | −0.002 (4) | 0.009 (5) |
C34A | 0.076 (5) | 0.028 (4) | 0.019 (3) | −0.025 (4) | 0.012 (3) | 0.000 (3) |
O8A | 0.090 (5) | 0.029 (3) | 0.025 (2) | 0.008 (3) | −0.002 (3) | −0.003 (2) |
V1—O1 | 1.9155 (17) | C13—H13 | 0.9300 |
V1—O2 | 1.9429 (16) | C18—H18 | 0.9300 |
V1—O3 | 1.6070 (17) | C18—C19 | 1.392 (4) |
V1—N1 | 2.0597 (19) | C1—H1 | 0.9300 |
V1—N2 | 2.051 (2) | C1—C2 | 1.381 (4) |
V2—O4 | 1.9164 (16) | C1—C6 | 1.393 (4) |
V2—O5 | 1.6089 (16) | C7—H7 | 0.9300 |
V2—O6 | 1.9314 (16) | C20—C23 | 1.440 (4) |
V2—N3 | 2.062 (2) | C20—C21 | 1.410 (3) |
V2—N4 | 2.060 (2) | C28—H28 | 0.9300 |
O6—C30 | 1.324 (3) | C28—C27 | 1.392 (5) |
O2—C12 | 1.326 (3) | C28—C29 | 1.381 (4) |
N4—C25 | 1.286 (3) | C2—H2 | 0.9300 |
N4—C31 | 1.469 (3) | C23—H23 | 0.9300 |
N2—C14 | 1.287 (3) | C16—H16A | 0.9700 |
N2—C16 | 1.476 (3) | C16—H16B | 0.9700 |
O1—C3 | 1.325 (3) | C5—H5 | 0.9300 |
C12—C9 | 1.424 (4) | C5—C6 | 1.375 (4) |
C12—C11 | 1.393 (4) | C21—H21 | 0.9300 |
O4—C22 | 1.321 (3) | C21—C19 | 1.380 (4) |
C14—H14 | 0.9300 | C11—H11 | 0.9300 |
C14—C9 | 1.439 (3) | C19—H19 | 0.9300 |
C30—C24 | 1.420 (4) | C27—H27 | 0.9300 |
C30—C29 | 1.406 (4) | C6—H6 | 0.9300 |
C3—C4 | 1.415 (3) | C29—H29 | 0.9300 |
C3—C2 | 1.405 (4) | C31—H31A | 0.9700 |
C25—H25 | 0.9300 | C31—H31B | 0.9700 |
C25—C24 | 1.442 (4) | C31—C32 | 1.511 (4) |
N1—C15 | 1.474 (3) | C32—H32A | 0.9700 |
N1—C13 | 1.286 (3) | C32—H32B | 0.9700 |
C26—H26 | 0.9300 | O8—H8A | 0.8200 |
C26—C24 | 1.401 (4) | O8—C34 | 1.416 (6) |
C26—C27 | 1.377 (4) | O7—H7A | 0.8200 |
N3—C23 | 1.286 (3) | O7—C33 | 1.407 (5) |
N3—C32 | 1.474 (3) | C33—H33A | 0.9600 |
C4—C13 | 1.443 (4) | C33—H33B | 0.9600 |
C4—C5 | 1.405 (3) | C33—H33C | 0.9600 |
C10—H10 | 0.9300 | C34—H34A | 0.9600 |
C10—C7 | 1.373 (5) | C34—H34B | 0.9600 |
C10—C11 | 1.393 (4) | C34—H34C | 0.9600 |
C8—H8 | 0.9300 | O7A—H7AA | 0.8200 |
C8—C9 | 1.411 (4) | O7A—C33A | 1.428 (9) |
C8—C7 | 1.379 (4) | C33A—H33D | 0.9600 |
C15—H15A | 0.9700 | C33A—H33E | 0.9600 |
C15—H15B | 0.9700 | C33A—H33F | 0.9600 |
C15—C16 | 1.520 (4) | C34A—H34D | 0.9600 |
C22—C17 | 1.405 (4) | C34A—H34E | 0.9600 |
C22—C20 | 1.419 (3) | C34A—H34F | 0.9600 |
C17—H17 | 0.9300 | C34A—O8A | 1.416 (7) |
C17—C18 | 1.376 (4) | O8A—H8AA | 0.8200 |
O2—V1—N2 | 87.30 (8) | C6—C1—H1 | 119.4 |
O2—V1—N1 | 150.78 (7) | C12—C9—C14 | 122.6 (2) |
O3—V1—O2 | 105.76 (8) | C8—C9—C12 | 118.7 (2) |
O3—V1—N2 | 107.35 (9) | C8—C9—C14 | 118.6 (2) |
O3—V1—O1 | 113.39 (8) | C10—C7—C8 | 119.7 (3) |
O3—V1—N1 | 102.90 (8) | C10—C7—H7 | 120.2 |
N2—V1—N1 | 78.80 (8) | C8—C7—H7 | 120.2 |
O1—V1—O2 | 86.60 (7) | C22—C20—C23 | 122.1 (2) |
O1—V1—N2 | 138.94 (8) | C21—C20—C22 | 119.7 (2) |
O1—V1—N1 | 87.26 (8) | C21—C20—C23 | 118.1 (2) |
O6—V2—N4 | 87.20 (8) | C27—C28—H28 | 119.6 |
O6—V2—N3 | 150.79 (7) | C29—C28—H28 | 119.6 |
O5—V2—O6 | 105.81 (8) | C29—C28—C27 | 120.7 (3) |
O5—V2—N4 | 107.66 (8) | C3—C2—H2 | 119.4 |
O5—V2—O4 | 113.60 (8) | C1—C2—C3 | 121.2 (2) |
O5—V2—N3 | 102.81 (8) | C1—C2—H2 | 119.4 |
N4—V2—N3 | 78.63 (8) | N3—C23—C20 | 124.6 (2) |
O4—V2—O6 | 86.66 (7) | N3—C23—H23 | 117.7 |
O4—V2—N4 | 138.40 (8) | C20—C23—H23 | 117.7 |
O4—V2—N3 | 87.25 (7) | N2—C16—C15 | 108.1 (2) |
C30—O6—V2 | 126.23 (15) | N2—C16—H16A | 110.1 |
C12—O2—V1 | 125.84 (15) | N2—C16—H16B | 110.1 |
C25—N4—V2 | 124.78 (18) | C15—C16—H16A | 110.1 |
C25—N4—C31 | 119.5 (2) | C15—C16—H16B | 110.1 |
C31—N4—V2 | 115.70 (15) | H16A—C16—H16B | 108.4 |
C14—N2—V1 | 125.24 (17) | C4—C5—H5 | 119.1 |
C14—N2—C16 | 118.9 (2) | C6—C5—C4 | 121.8 (2) |
C16—N2—V1 | 115.82 (15) | C6—C5—H5 | 119.1 |
C3—O1—V1 | 131.62 (15) | C20—C21—H21 | 119.3 |
O2—C12—C9 | 122.7 (2) | C19—C21—C20 | 121.3 (2) |
O2—C12—C11 | 118.8 (2) | C19—C21—H21 | 119.3 |
C11—C12—C9 | 118.4 (2) | C12—C11—C10 | 121.2 (3) |
C22—O4—V2 | 131.37 (15) | C12—C11—H11 | 119.4 |
N2—C14—H14 | 117.7 | C10—C11—H11 | 119.4 |
N2—C14—C9 | 124.5 (2) | C18—C19—H19 | 120.7 |
C9—C14—H14 | 117.7 | C21—C19—C18 | 118.7 (2) |
O6—C30—C24 | 123.4 (2) | C21—C19—H19 | 120.7 |
O6—C30—C29 | 119.0 (2) | C26—C27—C28 | 119.0 (3) |
C29—C30—C24 | 117.6 (2) | C26—C27—H27 | 120.5 |
O1—C3—C4 | 123.5 (2) | C28—C27—H27 | 120.5 |
O1—C3—C2 | 118.9 (2) | C1—C6—H6 | 120.8 |
C2—C3—C4 | 117.6 (2) | C5—C6—C1 | 118.4 (2) |
N4—C25—H25 | 117.3 | C5—C6—H6 | 120.8 |
N4—C25—C24 | 125.4 (2) | C30—C29—H29 | 119.3 |
C24—C25—H25 | 117.3 | C28—C29—C30 | 121.4 (3) |
C15—N1—V1 | 111.60 (15) | C28—C29—H29 | 119.3 |
C13—N1—V1 | 127.96 (17) | N4—C31—H31A | 110.0 |
C13—N1—C15 | 120.3 (2) | N4—C31—H31B | 110.0 |
C24—C26—H26 | 119.2 | N4—C31—C32 | 108.60 (19) |
C27—C26—H26 | 119.2 | H31A—C31—H31B | 108.4 |
C27—C26—C24 | 121.5 (3) | C32—C31—H31A | 110.0 |
C23—N3—V2 | 127.69 (17) | C32—C31—H31B | 110.0 |
C23—N3—C32 | 120.6 (2) | N3—C32—C31 | 106.66 (19) |
C32—N3—V2 | 111.60 (15) | N3—C32—H32A | 110.4 |
C3—C4—C13 | 122.6 (2) | N3—C32—H32B | 110.4 |
C5—C4—C3 | 119.7 (2) | C31—C32—H32A | 110.4 |
C5—C4—C13 | 117.6 (2) | C31—C32—H32B | 110.4 |
C7—C10—H10 | 119.7 | H32A—C32—H32B | 108.6 |
C7—C10—C11 | 120.5 (3) | C34—O8—H8A | 109.5 |
C11—C10—H10 | 119.7 | C33—O7—H7A | 109.5 |
C9—C8—H8 | 119.3 | O7—C33—H33A | 109.5 |
C7—C8—H8 | 119.3 | O7—C33—H33B | 109.5 |
C7—C8—C9 | 121.4 (3) | O7—C33—H33C | 109.5 |
N1—C15—H15A | 110.5 | H33A—C33—H33B | 109.5 |
N1—C15—H15B | 110.5 | H33A—C33—H33C | 109.5 |
N1—C15—C16 | 106.33 (19) | H33B—C33—H33C | 109.5 |
H15A—C15—H15B | 108.7 | O8—C34—H34A | 109.5 |
C16—C15—H15A | 110.5 | O8—C34—H34B | 109.5 |
C16—C15—H15B | 110.5 | O8—C34—H34C | 109.5 |
O4—C22—C17 | 118.7 (2) | H34A—C34—H34B | 109.5 |
O4—C22—C20 | 123.8 (2) | H34A—C34—H34C | 109.5 |
C17—C22—C20 | 117.5 (2) | H34B—C34—H34C | 109.5 |
C22—C17—H17 | 119.2 | C33A—O7A—H7AA | 109.5 |
C18—C17—C22 | 121.5 (2) | O7A—C33A—H33D | 109.5 |
C18—C17—H17 | 119.2 | O7A—C33A—H33E | 109.5 |
C30—C24—C25 | 121.7 (2) | O7A—C33A—H33F | 109.5 |
C26—C24—C30 | 119.7 (2) | H33D—C33A—H33E | 109.5 |
C26—C24—C25 | 118.6 (2) | H33D—C33A—H33F | 109.5 |
N1—C13—C4 | 124.1 (2) | H33E—C33A—H33F | 109.5 |
N1—C13—H13 | 117.9 | H34D—C34A—H34E | 109.5 |
C4—C13—H13 | 117.9 | H34D—C34A—H34F | 109.5 |
C17—C18—H18 | 119.4 | H34E—C34A—H34F | 109.5 |
C17—C18—C19 | 121.2 (3) | O8A—C34A—H34D | 109.5 |
C19—C18—H18 | 119.4 | O8A—C34A—H34E | 109.5 |
C2—C1—H1 | 119.4 | O8A—C34A—H34F | 109.5 |
C2—C1—C6 | 121.2 (3) | C34A—O8A—H8AA | 109.5 |
V2—O6—C30—C24 | −29.7 (3) | C4—C5—C6—C1 | −2.1 (4) |
V2—O6—C30—C29 | 151.31 (17) | C15—N1—C13—C4 | 177.3 (2) |
V2—N4—C25—C24 | 7.9 (3) | C22—C17—C18—C19 | −0.6 (4) |
V2—N4—C31—C32 | 22.2 (2) | C22—C20—C23—N3 | −7.4 (4) |
V2—O4—C22—C17 | −170.69 (17) | C22—C20—C21—C19 | −1.0 (3) |
V2—O4—C22—C20 | 11.4 (3) | C17—C22—C20—C23 | −172.0 (2) |
V2—N3—C23—C20 | −7.0 (3) | C17—C22—C20—C21 | 3.7 (3) |
V2—N3—C32—C31 | 46.0 (2) | C17—C18—C19—C21 | 3.4 (4) |
V1—O2—C12—C9 | −29.3 (3) | C24—C30—C29—C28 | 1.1 (3) |
V1—O2—C12—C11 | 153.17 (16) | C24—C26—C27—C28 | 1.1 (4) |
V1—N2—C14—C9 | 7.7 (3) | C13—N1—C15—C16 | −137.4 (2) |
V1—N2—C16—C15 | 22.8 (2) | C13—C4—C5—C6 | 175.5 (2) |
V1—O1—C3—C4 | 10.4 (3) | C9—C12—C11—C10 | 1.9 (3) |
V1—O1—C3—C2 | −170.93 (17) | C9—C8—C7—C10 | 1.7 (4) |
V1—N1—C15—C16 | 46.5 (2) | C7—C10—C11—C12 | −0.5 (4) |
V1—N1—C13—C4 | −7.2 (3) | C7—C8—C9—C12 | −0.2 (4) |
O6—C30—C24—C25 | −1.8 (3) | C7—C8—C9—C14 | −176.6 (2) |
O6—C30—C24—C26 | −179.2 (2) | C20—C22—C17—C18 | −3.0 (4) |
O6—C30—C29—C28 | −179.9 (2) | C20—C21—C19—C18 | −2.6 (4) |
O2—C12—C9—C14 | −2.8 (3) | C2—C3—C4—C13 | −172.5 (2) |
O2—C12—C9—C8 | −179.1 (2) | C2—C3—C4—C5 | 3.4 (3) |
O2—C12—C11—C10 | 179.6 (2) | C2—C1—C6—C5 | 1.9 (4) |
N4—C25—C24—C30 | 12.3 (4) | C23—N3—C32—C31 | −137.4 (2) |
N4—C25—C24—C26 | −170.2 (2) | C23—C20—C21—C19 | 174.9 (2) |
N4—C31—C32—N3 | −42.8 (2) | C16—N2—C14—C9 | −174.5 (2) |
N2—C14—C9—C12 | 13.4 (3) | C5—C4—C13—N1 | 176.9 (2) |
N2—C14—C9—C8 | −170.3 (2) | C21—C20—C23—N3 | 176.9 (2) |
O1—C3—C4—C13 | 6.2 (3) | C11—C12—C9—C14 | 174.7 (2) |
O1—C3—C4—C5 | −177.9 (2) | C11—C12—C9—C8 | −1.6 (3) |
O1—C3—C2—C1 | 177.6 (2) | C11—C10—C7—C8 | −1.3 (4) |
O4—C22—C17—C18 | 179.0 (2) | C27—C26—C24—C30 | −0.8 (4) |
O4—C22—C20—C23 | 5.9 (3) | C27—C26—C24—C25 | −178.4 (2) |
O4—C22—C20—C21 | −178.4 (2) | C27—C28—C29—C30 | −0.8 (4) |
C14—N2—C16—C15 | −155.1 (2) | C6—C1—C2—C3 | 1.1 (4) |
C3—C4—C13—N1 | −7.1 (4) | C29—C30—C24—C25 | 177.2 (2) |
C3—C4—C5—C6 | −0.6 (3) | C29—C30—C24—C26 | −0.3 (3) |
C25—N4—C31—C32 | −155.7 (2) | C29—C28—C27—C26 | −0.3 (4) |
N1—C15—C16—N2 | −43.4 (2) | C31—N4—C25—C24 | −174.5 (2) |
C4—C3—C2—C1 | −3.7 (4) | C32—N3—C23—C20 | 177.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O8i | 0.93 | 2.48 | 3.368 (4) | 159 |
C14—H14···O8Ai | 0.93 | 2.48 | 3.299 (7) | 147 |
C25—H25···O7ii | 0.93 | 2.51 | 3.391 (4) | 158 |
C25—H25···O7Aii | 0.93 | 2.66 | 3.457 (9) | 144 |
C13—H13···O3iii | 0.93 | 2.60 | 3.372 (3) | 141 |
C23—H23···O5iv | 0.93 | 2.59 | 3.364 (3) | 141 |
O8—H8A···O2 | 0.82 | 2.12 | 2.926 (4) | 167 |
O7—H7A···O6 | 0.82 | 2.18 | 2.940 (3) | 153 |
O7—H7A···O4 | 0.82 | 2.64 | 3.246 (4) | 132 |
O8A—H8AA···O1 | 0.82 | 2.18 | 2.984 (6) | 166 |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) x−1/2, −y+5/2, z; (iv) x−1/2, −y+1/2, z. |
V1—O1 | 1.9155 (17) | V2—O4 | 1.9164 (16) |
V1—O2 | 1.9429 (16) | V2—O5 | 1.6089 (16) |
V1—O3 | 1.6070 (17) | V2—O6 | 1.9314 (16) |
V1—N1 | 2.0597 (19) | V2—N3 | 2.062 (2) |
V1—N2 | 2.051 (2) | V2—N4 | 2.060 (2) |
O2—V1—N2 | 87.30 (8) | O6—V2—N4 | 87.20 (8) |
O2—V1—N1 | 150.78 (7) | O6—V2—N3 | 150.79 (7) |
O3—V1—O2 | 105.76 (8) | O5—V2—O6 | 105.81 (8) |
O3—V1—N2 | 107.35 (9) | O5—V2—N4 | 107.66 (8) |
O3—V1—O1 | 113.39 (8) | O5—V2—O4 | 113.60 (8) |
O3—V1—N1 | 102.90 (8) | O5—V2—N3 | 102.81 (8) |
N2—V1—N1 | 78.80 (8) | N4—V2—N3 | 78.63 (8) |
O1—V1—O2 | 86.60 (7) | O4—V2—O6 | 86.66 (7) |
O1—V1—N2 | 138.94 (8) | O4—V2—N4 | 138.40 (8) |
O1—V1—N1 | 87.26 (8) | O4—V2—N3 | 87.25 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O8i | 0.93 | 2.48 | 3.368 (4) | 159 |
C14—H14···O8Ai | 0.93 | 2.48 | 3.299 (7) | 147 |
C25—H25···O7ii | 0.93 | 2.51 | 3.391 (4) | 158 |
C25—H25···O7Aii | 0.93 | 2.66 | 3.457 (9) | 144 |
C13—H13···O3iii | 0.93 | 2.60 | 3.372 (3) | 141 |
C23—H23···O5iv | 0.93 | 2.59 | 3.364 (3) | 141 |
O8—H8A···O2 | 0.82 | 2.12 | 2.926 (4) | 167 |
O7—H7A···O6 | 0.82 | 2.18 | 2.940 (3) | 153 |
O7—H7A···O4 | 0.82 | 2.64 | 3.246 (4) | 132 |
O8A—H8AA···O1 | 0.82 | 2.18 | 2.984 (6) | 166 |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) x−1/2, −y+5/2, z; (iv) x−1/2, −y+1/2, z. |
Acknowledgements
We thank Professor A. N. Khlobystov for the sample of unsolvated {2,2′-[ethylenebis(nitrilomethylidyne)]diphenolato-κ4O,N,N′,O′}oxidovanadium(IV). We thank EPSRC (UK) for support.
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