Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049987/cf2153sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049987/cf2153Isup2.hkl |
CCDC reference: 667162
A mixture of vanadium(IV) sulfate (1 mmol) and N,N'-bis(2-hydroxybenzyl)-1,3-propanediamine (1 mmol) in 20 ml me thanol was refluxed for two hours. The above solution was filtered and the filtrate was allowed to evaporate naturally at room temperature. Two days later, blue blocks of (I) were obtained with a yield of 16%. Anal. calc. for C40H46V2N6O8: C 56.56, H 5.42, N 6.60%; found: C 56.52, H 5.44, N 6.51%.
All H atoms were placed in calculated positions with C—H = 0.93–0.96Å and refined as riding with Uiso(H) = 1.2 or 1.5 times Ueq(C).
Schiff base ligands have been studied for a long time due to their easy synthesis and versatile complexing properties. They play an important role in the development of coordination chemistry as well as inorganic biochemistry, catalysis, optical materials etc. (Garnovskii et al., 1993; Huang et al., 2002). The richness and importance of vanadate chemistry (Gresser & Tracey, 1986; Posner et al., 1994) have aroused our particular interest in designing new vanadium complexes with ONNO-donor ligands. In this paper, we report the structure of the title compound, (I).
As shown in Fig. 1, each V atom is chelated by a Schiff base ligand via two N and two O atoms. The two octahedrally coordinated V atoms are linked by two bridging oxide ligands to give a centrosymmetric dimer. The V—N and V—O bond lengths are in the ranges 2.028 (2)–2.078 (2) and 1.8187 (18)–1.9364 (19) %A, respectively.
For related literature, see: Garnovskii et al. (1993); Gresser & Tracey (1986); Huang et al. (2002); Posner et al. (1994).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).
Fig. 1. The molecular structure of (I), drawn with 30% probability displacement ellipsoids for the non-hydrogen atoms. [Symmetry code for unlabelled atoms: -x + 1, -y + 1, -z.] |
[V2(C17H17N2O2)2O2]·2C3H7NO | F(000) = 876 |
Mr = 840.71 | Dx = 1.467 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3265 reflections |
a = 10.9161 (5) Å | θ = 3.1–25.0° |
b = 9.9986 (5) Å | µ = 0.55 mm−1 |
c = 17.7812 (10) Å | T = 293 K |
β = 101.291 (2)° | Block, blue |
V = 1903.18 (17) Å3 | 0.43 × 0.28 × 0.22 mm |
Z = 2 |
Bruker APEXII CCD area-detector diffractometer | 3265 independent reflections |
Radiation source: fine-focus sealed tube | 2841 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ and ω scans | θmax = 25.0°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −12→12 |
Tmin = 0.797, Tmax = 0.888 | k = −11→11 |
10745 measured reflections | l = −20→20 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H-atom parameters not refined |
S = 1.00 | w = 1/[σ2(Fo2) + (0.089P)2 + 1.6075P] where P = (Fo2 + 2Fc2)/3 |
3265 reflections | (Δ/σ)max < 0.001 |
253 parameters | Δρmax = 0.95 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
[V2(C17H17N2O2)2O2]·2C3H7NO | V = 1903.18 (17) Å3 |
Mr = 840.71 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.9161 (5) Å | µ = 0.55 mm−1 |
b = 9.9986 (5) Å | T = 293 K |
c = 17.7812 (10) Å | 0.43 × 0.28 × 0.22 mm |
β = 101.291 (2)° |
Bruker APEXII CCD area-detector diffractometer | 3265 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2841 reflections with I > 2σ(I) |
Tmin = 0.797, Tmax = 0.888 | Rint = 0.032 |
10745 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.134 | H-atom parameters not refined |
S = 1.00 | Δρmax = 0.95 e Å−3 |
3265 reflections | Δρmin = −0.31 e Å−3 |
253 parameters |
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 | ||
V1 | 0.50502 (3) | 0.37734 (4) | 0.03285 (2) | 0.0161 (4) | |
O1 | 0.54652 (17) | 0.43578 (18) | 0.13786 (10) | 0.0216 (4) | |
O2 | 0.63819 (17) | 0.24749 (18) | 0.05886 (11) | 0.0231 (4) | |
N2 | 0.4575 (2) | 0.2833 (2) | −0.06976 (13) | 0.0201 (5) | |
C17 | 0.7134 (2) | 0.2146 (2) | 0.01051 (16) | 0.0214 (6) | |
N1 | 0.3655 (2) | 0.2627 (2) | 0.06550 (13) | 0.0211 (5) | |
C11 | 0.5372 (3) | 0.2249 (2) | −0.10443 (15) | 0.0214 (6) | |
H11A | 0.5080 | 0.1932 | −0.1539 | 0.026* | |
C16 | 0.8407 (3) | 0.1822 (3) | 0.04046 (16) | 0.0242 (6) | |
H16A | 0.8714 | 0.1874 | 0.0930 | 0.029* | |
C10 | 0.3227 (3) | 0.2801 (3) | −0.10458 (16) | 0.0245 (6) | |
H10A | 0.3121 | 0.2555 | −0.1582 | 0.029* | |
H10B | 0.2871 | 0.3684 | −0.1017 | 0.029* | |
C5 | 0.2591 (3) | 0.4421 (3) | 0.22177 (16) | 0.0276 (6) | |
H5A | 0.1824 | 0.3990 | 0.2169 | 0.033* | |
C7 | 0.3077 (2) | 0.2952 (3) | 0.12027 (16) | 0.0233 (6) | |
H7A | 0.2386 | 0.2444 | 0.1258 | 0.028* | |
C1 | 0.4629 (2) | 0.4667 (3) | 0.18088 (14) | 0.0201 (6) | |
C8 | 0.3227 (3) | 0.1436 (3) | 0.01943 (17) | 0.0268 (6) | |
H8A | 0.2677 | 0.0922 | 0.0451 | 0.032* | |
H8B | 0.3944 | 0.0881 | 0.0161 | 0.032* | |
C15 | 0.9199 (3) | 0.1426 (3) | −0.00830 (18) | 0.0276 (6) | |
H15A | 1.0029 | 0.1229 | 0.0124 | 0.033* | |
C9 | 0.2529 (3) | 0.1782 (3) | −0.06243 (17) | 0.0311 (7) | |
H9A | 0.1715 | 0.2144 | −0.0596 | 0.037* | |
H9B | 0.2397 | 0.0965 | −0.0924 | 0.037* | |
C2 | 0.4954 (3) | 0.5621 (3) | 0.24014 (16) | 0.0256 (6) | |
H2A | 0.5749 | 0.5997 | 0.2493 | 0.031* | |
C6 | 0.3432 (3) | 0.4046 (3) | 0.17318 (16) | 0.0224 (6) | |
C4 | 0.2908 (3) | 0.5423 (3) | 0.27629 (16) | 0.0285 (6) | |
H4A | 0.2345 | 0.5701 | 0.3062 | 0.034* | |
C12 | 0.6699 (3) | 0.2055 (3) | −0.07122 (16) | 0.0226 (6) | |
C14 | 0.8766 (3) | 0.1315 (3) | −0.08890 (19) | 0.0320 (7) | |
H14A | 0.9301 | 0.1044 | −0.1207 | 0.038* | |
C13 | 0.7522 (3) | 0.1622 (3) | −0.11906 (17) | 0.0266 (6) | |
H13A | 0.7224 | 0.1542 | −0.1716 | 0.032* | |
C3 | 0.4097 (3) | 0.6008 (3) | 0.28523 (17) | 0.0285 (7) | |
H3A | 0.4321 | 0.6670 | 0.3221 | 0.034* | |
N3 | 0.9330 (2) | 0.5321 (3) | 0.16965 (14) | 0.0329 (6) | |
O4 | 0.9442 (2) | 0.6587 (3) | 0.27878 (13) | 0.0459 (6) | |
C18 | 0.9720 (3) | 0.6352 (3) | 0.2145 (2) | 0.0376 (8) | |
H18A | 1.0246 | 0.6960 | 0.1970 | 0.045* | |
C19 | 0.8517 (3) | 0.4318 (3) | 0.1944 (2) | 0.0375 (7) | |
H19A | 0.8365 | 0.4553 | 0.2441 | 0.056* | |
H19B | 0.8913 | 0.3458 | 0.1969 | 0.056* | |
H19C | 0.7737 | 0.4286 | 0.1584 | 0.056* | |
C20 | 0.9680 (3) | 0.5130 (4) | 0.09462 (19) | 0.0442 (8) | |
H20A | 1.0212 | 0.5850 | 0.0852 | 0.066* | |
H20B | 0.8941 | 0.5118 | 0.0552 | 0.066* | |
H20C | 1.0117 | 0.4296 | 0.0944 | 0.066* | |
O3 | 0.39013 (16) | 0.50834 (18) | 0.00318 (10) | 0.0204 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
V1 | 0.0171 (9) | 0.0190 (9) | 0.0131 (9) | 0.0006 (7) | 0.0049 (7) | −0.0003 (7) |
O1 | 0.0235 (10) | 0.0223 (10) | 0.0197 (10) | 0.0004 (7) | 0.0059 (8) | 0.0003 (8) |
O2 | 0.0258 (10) | 0.0210 (9) | 0.0236 (10) | 0.0038 (7) | 0.0076 (8) | 0.0012 (8) |
N2 | 0.0218 (11) | 0.0163 (11) | 0.0228 (12) | −0.0016 (8) | 0.0059 (9) | 0.0018 (9) |
C17 | 0.0253 (14) | 0.0131 (12) | 0.0271 (15) | 0.0006 (10) | 0.0087 (11) | 0.0021 (10) |
N1 | 0.0228 (11) | 0.0200 (11) | 0.0208 (12) | 0.0006 (9) | 0.0052 (9) | 0.0010 (9) |
C11 | 0.0314 (15) | 0.0155 (12) | 0.0183 (14) | −0.0023 (10) | 0.0074 (11) | −0.0001 (10) |
C16 | 0.0273 (15) | 0.0199 (14) | 0.0264 (15) | −0.0009 (11) | 0.0074 (12) | 0.0025 (11) |
C10 | 0.0254 (14) | 0.0231 (14) | 0.0245 (15) | −0.0036 (11) | 0.0034 (11) | −0.0032 (11) |
C5 | 0.0294 (15) | 0.0291 (15) | 0.0267 (15) | 0.0021 (12) | 0.0114 (12) | 0.0026 (12) |
C7 | 0.0209 (13) | 0.0214 (14) | 0.0286 (15) | 0.0013 (10) | 0.0069 (11) | 0.0046 (11) |
C1 | 0.0235 (13) | 0.0206 (13) | 0.0165 (13) | 0.0042 (10) | 0.0048 (10) | 0.0038 (10) |
C8 | 0.0273 (15) | 0.0190 (13) | 0.0362 (17) | −0.0053 (11) | 0.0119 (13) | −0.0014 (12) |
C15 | 0.0209 (14) | 0.0243 (14) | 0.0385 (18) | 0.0026 (11) | 0.0077 (12) | 0.0030 (13) |
C9 | 0.0320 (16) | 0.0331 (16) | 0.0292 (17) | −0.0111 (13) | 0.0085 (13) | −0.0065 (13) |
C2 | 0.0312 (15) | 0.0225 (14) | 0.0235 (15) | −0.0021 (11) | 0.0068 (12) | −0.0002 (12) |
C6 | 0.0242 (14) | 0.0210 (13) | 0.0224 (15) | 0.0034 (11) | 0.0059 (11) | 0.0028 (11) |
C4 | 0.0340 (16) | 0.0300 (15) | 0.0245 (16) | 0.0068 (12) | 0.0128 (12) | 0.0022 (12) |
C12 | 0.0288 (15) | 0.0150 (13) | 0.0257 (15) | 0.0005 (10) | 0.0092 (12) | 0.0015 (11) |
C14 | 0.0297 (16) | 0.0296 (16) | 0.0423 (19) | 0.0030 (12) | 0.0205 (14) | 0.0019 (13) |
C13 | 0.0324 (16) | 0.0236 (14) | 0.0254 (15) | 0.0011 (12) | 0.0097 (12) | 0.0006 (12) |
C3 | 0.0391 (17) | 0.0245 (14) | 0.0225 (16) | 0.0021 (12) | 0.0078 (13) | −0.0017 (11) |
N3 | 0.0333 (14) | 0.0319 (14) | 0.0324 (15) | 0.0003 (11) | 0.0037 (11) | 0.0008 (11) |
O4 | 0.0515 (15) | 0.0464 (14) | 0.0384 (14) | −0.0017 (11) | 0.0051 (11) | −0.0102 (11) |
C18 | 0.0338 (17) | 0.0344 (18) | 0.043 (2) | −0.0042 (13) | 0.0033 (15) | −0.0017 (14) |
C19 | 0.0357 (17) | 0.0321 (17) | 0.044 (2) | −0.0005 (13) | 0.0068 (14) | 0.0001 (14) |
C20 | 0.048 (2) | 0.043 (2) | 0.042 (2) | −0.0009 (16) | 0.0111 (16) | −0.0048 (16) |
O3 | 0.0210 (10) | 0.0190 (9) | 0.0217 (10) | 0.0001 (7) | 0.0053 (7) | 0.0007 (8) |
V1—O3 | 1.8187 (18) | C8—C9 | 1.544 (4) |
V1—O3i | 1.8204 (17) | C8—H8A | 0.970 |
V1—O1 | 1.9240 (18) | C8—H8B | 0.970 |
V1—O2 | 1.9364 (19) | C15—C14 | 1.423 (5) |
V1—N2 | 2.028 (2) | C15—H15A | 0.930 |
V1—N1 | 2.078 (2) | C9—H9A | 0.970 |
V1—V1i | 2.7098 (7) | C9—H9B | 0.970 |
O1—C1 | 1.337 (3) | C2—C3 | 1.401 (4) |
O2—C17 | 1.340 (3) | C2—H2A | 0.930 |
N2—C11 | 1.299 (3) | C4—C3 | 1.403 (4) |
N2—C10 | 1.481 (3) | C4—H4A | 0.930 |
C17—C16 | 1.425 (4) | C12—C13 | 1.420 (4) |
C17—C12 | 1.441 (4) | C14—C13 | 1.393 (4) |
N1—C7 | 1.301 (3) | C14—H14A | 0.930 |
N1—C8 | 1.468 (3) | C13—H13A | 0.930 |
C11—C12 | 1.467 (4) | C3—H3A | 0.930 |
C11—H11A | 0.930 | N3—C18 | 1.322 (4) |
C16—C15 | 1.396 (4) | N3—C19 | 1.463 (4) |
C16—H16A | 0.930 | N3—C20 | 1.470 (4) |
C10—C9 | 1.550 (4) | O4—C18 | 1.261 (4) |
C10—H10A | 0.970 | C18—H18A | 0.930 |
C10—H10B | 0.970 | C19—H19A | 0.960 |
C5—C4 | 1.391 (4) | C19—H19B | 0.960 |
C5—C6 | 1.428 (4) | C19—H19C | 0.960 |
C5—H5A | 0.930 | C20—H20A | 0.960 |
C7—C6 | 1.446 (4) | C20—H20B | 0.960 |
C7—H7A | 0.930 | C20—H20C | 0.960 |
C1—C2 | 1.414 (4) | O3—V1i | 1.8204 (17) |
C1—C6 | 1.430 (4) | ||
O3—V1—O3i | 83.74 (8) | N1—C8—H8A | 109.0 |
O3—V1—O1 | 94.64 (8) | C9—C8—H8A | 109.0 |
O3i—V1—O1 | 96.08 (8) | N1—C8—H8B | 109.0 |
O3—V1—O2 | 174.25 (8) | C9—C8—H8B | 109.0 |
O3i—V1—O2 | 90.61 (8) | H8A—C8—H8B | 107.8 |
O1—V1—O2 | 87.06 (8) | C16—C15—C14 | 121.6 (3) |
O3—V1—N2 | 91.86 (8) | C16—C15—H15A | 119.2 |
O3i—V1—N2 | 92.43 (8) | C14—C15—H15A | 119.2 |
O1—V1—N2 | 169.80 (8) | C8—C9—C10 | 113.9 (2) |
O2—V1—N2 | 87.24 (8) | C8—C9—H9A | 108.8 |
O3—V1—N1 | 88.68 (8) | C10—C9—H9A | 108.8 |
O3i—V1—N1 | 172.10 (8) | C8—C9—H9B | 108.8 |
O1—V1—N1 | 86.71 (8) | C10—C9—H9B | 108.8 |
O2—V1—N1 | 96.92 (8) | H9A—C9—H9B | 107.7 |
N2—V1—N1 | 85.58 (9) | C3—C2—C1 | 120.9 (3) |
O3—V1—V1i | 41.90 (5) | C3—C2—H2A | 119.5 |
O3i—V1—V1i | 41.85 (6) | C1—C2—H2A | 119.5 |
O1—V1—V1i | 97.21 (6) | C5—C6—C1 | 120.8 (3) |
O2—V1—V1i | 132.45 (6) | C5—C6—C7 | 118.1 (2) |
N2—V1—V1i | 92.88 (6) | C1—C6—C7 | 121.0 (2) |
N1—V1—V1i | 130.54 (7) | C5—C4—C3 | 118.6 (3) |
C1—O1—V1 | 124.62 (16) | C5—C4—H4A | 120.7 |
C17—O2—V1 | 122.43 (17) | C3—C4—H4A | 120.7 |
C11—N2—C10 | 119.7 (2) | C13—C12—C17 | 120.1 (3) |
C11—N2—V1 | 123.91 (19) | C13—C12—C11 | 119.3 (3) |
C10—N2—V1 | 116.40 (16) | C17—C12—C11 | 120.1 (2) |
O2—C17—C16 | 119.4 (2) | C13—C14—C15 | 118.5 (3) |
O2—C17—C12 | 122.7 (2) | C13—C14—H14A | 120.8 |
C16—C17—C12 | 117.8 (2) | C15—C14—H14A | 120.8 |
C7—N1—C8 | 118.2 (2) | C14—C13—C12 | 121.3 (3) |
C7—N1—V1 | 124.11 (19) | C14—C13—H13A | 119.3 |
C8—N1—V1 | 117.49 (16) | C12—C13—H13A | 119.3 |
N2—C11—C12 | 124.7 (2) | C2—C3—C4 | 121.8 (3) |
N2—C11—H11A | 117.7 | C2—C3—H3A | 119.1 |
C12—C11—H11A | 117.7 | C4—C3—H3A | 119.1 |
C15—C16—C17 | 120.6 (3) | C18—N3—C19 | 119.7 (3) |
C15—C16—H16A | 119.7 | C18—N3—C20 | 122.6 (3) |
C17—C16—H16A | 119.7 | C19—N3—C20 | 117.7 (3) |
N2—C10—C9 | 110.7 (2) | O4—C18—N3 | 125.9 (3) |
N2—C10—H10A | 109.5 | O4—C18—H18A | 117.0 |
C9—C10—H10A | 109.5 | N3—C18—H18A | 117.0 |
N2—C10—H10B | 109.5 | N3—C19—H19A | 109.5 |
C9—C10—H10B | 109.5 | N3—C19—H19B | 109.5 |
H10A—C10—H10B | 108.1 | H19A—C19—H19B | 109.5 |
C4—C5—C6 | 120.6 (3) | N3—C19—H19C | 109.5 |
C4—C5—H5A | 119.7 | H19A—C19—H19C | 109.5 |
C6—C5—H5A | 119.7 | H19B—C19—H19C | 109.5 |
N1—C7—C6 | 124.7 (2) | N3—C20—H20A | 109.5 |
N1—C7—H7A | 117.7 | N3—C20—H20B | 109.5 |
C6—C7—H7A | 117.7 | H20A—C20—H20B | 109.5 |
O1—C1—C2 | 118.8 (2) | N3—C20—H20C | 109.5 |
O1—C1—C6 | 123.9 (2) | H20A—C20—H20C | 109.5 |
C2—C1—C6 | 117.1 (2) | H20B—C20—H20C | 109.5 |
N1—C8—C9 | 112.9 (2) | V1—O3—V1i | 96.26 (8) |
Symmetry code: (i) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | [V2(C17H17N2O2)2O2]·2C3H7NO |
Mr | 840.71 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 10.9161 (5), 9.9986 (5), 17.7812 (10) |
β (°) | 101.291 (2) |
V (Å3) | 1903.18 (17) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.55 |
Crystal size (mm) | 0.43 × 0.28 × 0.22 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.797, 0.888 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10745, 3265, 2841 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.134, 1.00 |
No. of reflections | 3265 |
No. of parameters | 253 |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.95, −0.31 |
Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).
Schiff base ligands have been studied for a long time due to their easy synthesis and versatile complexing properties. They play an important role in the development of coordination chemistry as well as inorganic biochemistry, catalysis, optical materials etc. (Garnovskii et al., 1993; Huang et al., 2002). The richness and importance of vanadate chemistry (Gresser & Tracey, 1986; Posner et al., 1994) have aroused our particular interest in designing new vanadium complexes with ONNO-donor ligands. In this paper, we report the structure of the title compound, (I).
As shown in Fig. 1, each V atom is chelated by a Schiff base ligand via two N and two O atoms. The two octahedrally coordinated V atoms are linked by two bridging oxide ligands to give a centrosymmetric dimer. The V—N and V—O bond lengths are in the ranges 2.028 (2)–2.078 (2) and 1.8187 (18)–1.9364 (19) %A, respectively.