Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806016680/cs2004sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806016680/cs2004Isup2.hkl |
CCDC reference: 610738
Data collection: COLLECT (Nonius, 1998); cell refinement: HKL-2000 (Otwinowski & Minor, 1997); data reduction: HKL-2000; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
[Na3(C5H7O2)3(C5H5N)] | F(000) = 936 |
Mr = 445.39 | Dx = 1.273 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 16242 reflections |
a = 10.8858 (13) Å | θ = 2.1–25.7° |
b = 18.969 (2) Å | µ = 0.14 mm−1 |
c = 12.1338 (12) Å | T = 100 K |
β = 111.941 (7)° | Irregular, colourless |
V = 2324.1 (5) Å3 | 0.14 × 0.12 × 0.09 mm |
Z = 4 |
Nonius KappaCCD area-detector diffractometer | 2999 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.065 |
Graphite monochromator | θmax = 25.7°, θmin = 2.1° |
φ scan with 2° steps | h = 0→13 |
16242 measured reflections | k = 0→23 |
4353 independent reflections | l = −14→13 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0521P)2 + 0.6412P] where P = (Fo2 + 2Fc2)/3 |
4353 reflections | (Δ/σ)max < 0.001 |
277 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Experimental. crystal-to-detector distance 30 mm |
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. Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms were introduced at calculated positions and were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (CH) or 1.5 (CH3) times that of the parent atom. 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 | ||
Na1 | 0.67782 (10) | 0.07025 (5) | 0.70263 (8) | 0.0409 (3) | |
Na2 | 0.51509 (10) | 0.06945 (5) | 0.41192 (9) | 0.0428 (3) | |
Na3 | 0.52947 (10) | −0.00977 (5) | 0.87299 (8) | 0.0391 (3) | |
O1 | 0.66005 (18) | −0.00587 (9) | 0.54916 (15) | 0.0418 (4) | |
O2 | 0.67105 (18) | −0.04351 (9) | 0.77762 (15) | 0.0414 (4) | |
O3 | 0.55536 (19) | 0.10101 (9) | 0.80662 (16) | 0.0456 (4) | |
O4 | 0.52702 (18) | 0.14394 (9) | 0.56849 (15) | 0.0436 (4) | |
O5 | 0.64935 (17) | 0.01639 (9) | 1.07117 (14) | 0.0406 (4) | |
O6 | 0.61308 (18) | 0.08015 (9) | 1.27572 (15) | 0.0443 (4) | |
N1 | 0.8887 (2) | 0.12571 (11) | 0.73372 (18) | 0.0437 (5) | |
C1 | 0.7965 (3) | −0.07008 (15) | 0.4716 (3) | 0.0539 (7) | |
H1A | 0.7227 | −0.0769 | 0.3981 | 0.081* | |
H1B | 0.8496 | −0.1120 | 0.4908 | 0.081* | |
H1C | 0.8491 | −0.0312 | 0.4637 | 0.081* | |
C2 | 0.7463 (3) | −0.05450 (13) | 0.5693 (2) | 0.0418 (6) | |
C3 | 0.7951 (3) | −0.09427 (13) | 0.6744 (2) | 0.0426 (6) | |
H3 | 0.8599 | −0.1276 | 0.6804 | 0.051* | |
C4 | 0.7545 (3) | −0.08808 (12) | 0.7715 (2) | 0.0394 (6) | |
C5 | 0.8112 (3) | −0.13842 (14) | 0.8743 (2) | 0.0473 (7) | |
H5A | 0.8699 | −0.1134 | 0.9424 | 0.071* | |
H5B | 0.8592 | −0.1751 | 0.8532 | 0.071* | |
H5C | 0.7405 | −0.1589 | 0.8927 | 0.071* | |
C6 | 0.4969 (3) | 0.18500 (16) | 0.9221 (3) | 0.0609 (8) | |
H6A | 0.4301 | 0.1572 | 0.9353 | 0.091* | |
H6B | 0.4723 | 0.2339 | 0.9165 | 0.091* | |
H6C | 0.5800 | 0.1786 | 0.9870 | 0.091* | |
C7 | 0.5102 (3) | 0.16187 (14) | 0.8070 (2) | 0.0439 (6) | |
C8 | 0.4701 (3) | 0.20861 (13) | 0.7104 (2) | 0.0449 (6) | |
H8 | 0.4392 | 0.2525 | 0.7225 | 0.054* | |
C9 | 0.4720 (3) | 0.19551 (13) | 0.5969 (2) | 0.0434 (6) | |
C10 | 0.4007 (3) | 0.24749 (15) | 0.4991 (3) | 0.0556 (8) | |
H10A | 0.4605 | 0.2643 | 0.4636 | 0.083* | |
H10B | 0.3697 | 0.2865 | 0.5320 | 0.083* | |
H10C | 0.3268 | 0.2246 | 0.4398 | 0.083* | |
C11 | 0.8441 (3) | 0.05105 (14) | 1.0420 (2) | 0.0452 (6) | |
H11A | 0.8466 | 0.0047 | 1.0110 | 0.068* | |
H11B | 0.9320 | 0.0651 | 1.0920 | 0.068* | |
H11C | 0.8092 | 0.0838 | 0.9775 | 0.068* | |
C12 | 0.7562 (3) | 0.05029 (13) | 1.1139 (2) | 0.0391 (6) | |
C13 | 0.8006 (3) | 0.08803 (13) | 1.2213 (2) | 0.0413 (6) | |
H13 | 0.8847 | 0.1078 | 1.2449 | 0.050* | |
C14 | 0.7312 (3) | 0.09903 (13) | 1.2967 (2) | 0.0419 (6) | |
C15 | 0.8015 (3) | 0.13651 (15) | 1.4135 (2) | 0.0508 (7) | |
H15A | 0.7511 | 0.1771 | 1.4183 | 0.076* | |
H15B | 0.8878 | 0.1511 | 1.4183 | 0.076* | |
H15C | 0.8101 | 0.1051 | 1.4780 | 0.076* | |
C16 | 1.0026 (3) | 0.09108 (15) | 0.7556 (2) | 0.0495 (7) | |
H16 | 1.0035 | 0.0426 | 0.7676 | 0.059* | |
C17 | 1.1183 (3) | 0.12289 (17) | 0.7612 (3) | 0.0566 (8) | |
H17 | 1.1954 | 0.0967 | 0.7786 | 0.068* | |
C18 | 1.1175 (3) | 0.19442 (17) | 0.7407 (3) | 0.0569 (8) | |
H18 | 1.1939 | 0.2173 | 0.7427 | 0.068* | |
C19 | 1.0020 (3) | 0.23123 (15) | 0.7173 (3) | 0.0534 (7) | |
H19 | 0.9987 | 0.2795 | 0.7034 | 0.064* | |
C20 | 0.8906 (3) | 0.19509 (14) | 0.7148 (2) | 0.0483 (7) | |
H20 | 0.8127 | 0.2204 | 0.6990 | 0.058* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Na1 | 0.0444 (6) | 0.0387 (5) | 0.0406 (5) | 0.0005 (4) | 0.0170 (5) | −0.0019 (4) |
Na2 | 0.0438 (6) | 0.0470 (6) | 0.0386 (5) | −0.0030 (5) | 0.0165 (5) | −0.0015 (4) |
Na3 | 0.0395 (6) | 0.0419 (5) | 0.0366 (5) | −0.0020 (4) | 0.0150 (4) | −0.0013 (4) |
O1 | 0.0442 (11) | 0.0406 (10) | 0.0421 (10) | 0.0007 (8) | 0.0180 (9) | −0.0036 (8) |
O2 | 0.0437 (11) | 0.0395 (9) | 0.0420 (10) | 0.0032 (8) | 0.0172 (8) | −0.0009 (8) |
O3 | 0.0544 (12) | 0.0388 (10) | 0.0483 (10) | 0.0068 (9) | 0.0246 (9) | 0.0028 (8) |
O4 | 0.0484 (11) | 0.0391 (10) | 0.0422 (10) | 0.0005 (8) | 0.0158 (9) | −0.0008 (8) |
O5 | 0.0377 (10) | 0.0465 (10) | 0.0374 (9) | −0.0060 (8) | 0.0136 (8) | −0.0020 (8) |
O6 | 0.0458 (11) | 0.0496 (11) | 0.0389 (10) | −0.0093 (9) | 0.0175 (9) | −0.0057 (8) |
N1 | 0.0449 (14) | 0.0446 (13) | 0.0401 (12) | 0.0012 (10) | 0.0140 (10) | −0.0019 (10) |
C1 | 0.0582 (19) | 0.0580 (17) | 0.0548 (17) | 0.0047 (15) | 0.0318 (16) | −0.0058 (14) |
C2 | 0.0396 (15) | 0.0403 (14) | 0.0470 (15) | −0.0065 (12) | 0.0180 (13) | −0.0084 (12) |
C3 | 0.0375 (15) | 0.0408 (14) | 0.0484 (15) | 0.0008 (12) | 0.0148 (12) | −0.0033 (12) |
C4 | 0.0343 (14) | 0.0342 (13) | 0.0468 (15) | −0.0021 (11) | 0.0118 (12) | −0.0033 (11) |
C5 | 0.0463 (17) | 0.0399 (14) | 0.0528 (16) | 0.0009 (12) | 0.0150 (13) | 0.0015 (12) |
C6 | 0.072 (2) | 0.0615 (19) | 0.0527 (18) | 0.0195 (17) | 0.0274 (17) | −0.0031 (15) |
C7 | 0.0451 (16) | 0.0406 (14) | 0.0476 (15) | 0.0034 (12) | 0.0191 (13) | −0.0022 (12) |
C8 | 0.0484 (17) | 0.0342 (13) | 0.0515 (16) | 0.0015 (12) | 0.0178 (13) | −0.0030 (12) |
C9 | 0.0427 (16) | 0.0343 (13) | 0.0505 (16) | −0.0034 (12) | 0.0141 (13) | 0.0000 (12) |
C10 | 0.060 (2) | 0.0449 (16) | 0.0492 (17) | 0.0009 (14) | 0.0059 (15) | 0.0017 (13) |
C11 | 0.0392 (15) | 0.0504 (15) | 0.0469 (15) | −0.0060 (12) | 0.0171 (13) | −0.0029 (12) |
C12 | 0.0378 (15) | 0.0391 (13) | 0.0390 (14) | −0.0021 (12) | 0.0125 (12) | 0.0041 (11) |
C13 | 0.0388 (15) | 0.0407 (14) | 0.0426 (14) | −0.0082 (11) | 0.0131 (12) | −0.0036 (11) |
C14 | 0.0458 (17) | 0.0390 (14) | 0.0381 (14) | −0.0072 (12) | 0.0127 (12) | −0.0003 (11) |
C15 | 0.0554 (19) | 0.0509 (16) | 0.0435 (15) | −0.0111 (14) | 0.0154 (14) | −0.0076 (13) |
C16 | 0.0509 (18) | 0.0512 (16) | 0.0457 (16) | 0.0039 (14) | 0.0173 (14) | −0.0014 (13) |
C17 | 0.0514 (19) | 0.067 (2) | 0.0526 (17) | 0.0095 (15) | 0.0214 (15) | −0.0042 (15) |
C18 | 0.0512 (19) | 0.071 (2) | 0.0512 (17) | −0.0104 (16) | 0.0218 (15) | −0.0063 (15) |
C19 | 0.059 (2) | 0.0469 (16) | 0.0521 (17) | −0.0076 (14) | 0.0178 (15) | −0.0019 (13) |
C20 | 0.0511 (18) | 0.0417 (15) | 0.0499 (16) | −0.0011 (13) | 0.0162 (14) | −0.0050 (12) |
Na1—O1 | 2.307 (2) | C2—C3 | 1.403 (4) |
Na1—O2 | 2.354 (2) | C3—C4 | 1.410 (3) |
Na1—O3 | 2.229 (2) | C3—H3 | 0.9300 |
Na1—O4 | 2.302 (2) | C4—C5 | 1.508 (4) |
Na1—N1 | 2.423 (2) | C5—H5A | 0.9600 |
Na1—Na2 | 3.3032 (14) | C5—H5B | 0.9600 |
Na1—Na2i | 3.3442 (14) | C5—H5C | 0.9600 |
Na1—Na3 | 3.4175 (13) | C6—C7 | 1.522 (4) |
Na2—O1 | 2.311 (2) | C6—H6A | 0.9600 |
Na2—O1i | 2.447 (2) | C6—H6B | 0.9600 |
Na2—O2i | 2.481 (2) | C6—H6C | 0.9600 |
Na2—O4 | 2.332 (2) | C7—C8 | 1.403 (4) |
Na2—O6ii | 2.286 (2) | C8—C9 | 1.407 (4) |
Na2—Na2i | 3.4850 (19) | C8—H8 | 0.9300 |
Na2—Na3i | 3.4949 (13) | C9—C10 | 1.514 (4) |
Na3—O2 | 2.336 (2) | C10—H10A | 0.9600 |
Na3—O3 | 2.305 (2) | C10—H10B | 0.9600 |
Na3—O5 | 2.321 (2) | C10—H10C | 0.9600 |
Na3—O5iii | 2.291 (2) | C11—C12 | 1.516 (3) |
Na3—O6iii | 2.314 (2) | C11—H11A | 0.9600 |
Na3—Na3iii | 3.3953 (18) | C11—H11B | 0.9600 |
O1—C2 | 1.273 (3) | C11—H11C | 0.9600 |
O1—Na2i | 2.447 (2) | C12—C13 | 1.405 (3) |
O2—C4 | 1.264 (3) | C13—C14 | 1.403 (3) |
O2—Na2i | 2.481 (2) | C13—H13 | 0.9300 |
O3—C7 | 1.255 (3) | C14—C15 | 1.513 (4) |
O4—C9 | 1.260 (3) | C15—H15A | 0.9600 |
O5—C12 | 1.259 (3) | C15—H15B | 0.9600 |
O5—Na3iii | 2.2913 (19) | C15—H15C | 0.9600 |
O6—C14 | 1.266 (3) | C16—C17 | 1.375 (4) |
O6—Na2iv | 2.2864 (18) | C16—H16 | 0.9300 |
O6—Na3iii | 2.314 (2) | C17—C18 | 1.379 (4) |
N1—C20 | 1.338 (3) | C17—H17 | 0.9300 |
N1—C16 | 1.339 (3) | C18—C19 | 1.372 (4) |
C1—C2 | 1.509 (3) | C18—H18 | 0.9300 |
C1—H1A | 0.9600 | C19—C20 | 1.384 (4) |
C1—H1B | 0.9600 | C19—H19 | 0.9300 |
C1—H1C | 0.9600 | C20—H20 | 0.9300 |
O3—Na1—O4 | 79.74 (7) | C4—C3—H3 | 117.1 |
O3—Na1—O1 | 137.18 (8) | O2—C4—C3 | 124.2 (2) |
O4—Na1—O1 | 89.24 (7) | O2—C4—C5 | 117.1 (2) |
O3—Na1—O2 | 84.80 (7) | C3—C4—C5 | 118.7 (2) |
O4—Na1—O2 | 135.47 (8) | C4—C5—H5A | 109.5 |
O1—Na1—O2 | 74.51 (6) | C4—C5—H5B | 109.5 |
O3—Na1—N1 | 122.04 (8) | H5A—C5—H5B | 109.5 |
O4—Na1—N1 | 103.31 (8) | C4—C5—H5C | 109.5 |
O1—Na1—N1 | 100.73 (7) | H5A—C5—H5C | 109.5 |
O2—Na1—N1 | 120.16 (8) | H5B—C5—H5C | 109.5 |
O6ii—Na2—O1 | 101.44 (7) | C7—C6—H6A | 109.5 |
O6ii—Na2—O4 | 129.50 (7) | C7—C6—H6B | 109.5 |
O1—Na2—O4 | 88.42 (7) | H6A—C6—H6B | 109.5 |
O6ii—Na2—O1i | 142.28 (7) | C7—C6—H6C | 109.5 |
O1—Na2—O1i | 85.85 (7) | H6A—C6—H6C | 109.5 |
O4—Na2—O1i | 87.23 (7) | H6B—C6—H6C | 109.5 |
O6ii—Na2—O2i | 77.74 (7) | O3—C7—C8 | 125.3 (2) |
O1—Na2—O2i | 130.29 (7) | O3—C7—C6 | 116.1 (2) |
O4—Na2—O2i | 130.77 (7) | C8—C7—C6 | 118.6 (2) |
O1i—Na2—O2i | 69.86 (6) | C7—C8—C9 | 126.3 (2) |
O5iii—Na3—O3 | 112.43 (7) | C7—C8—H8 | 116.8 |
O5iii—Na3—O6iii | 78.62 (7) | C9—C8—H8 | 116.8 |
O3—Na3—O6iii | 112.80 (7) | O4—C9—C8 | 125.9 (2) |
O5iii—Na3—O5 | 85.19 (7) | O4—C9—C10 | 116.6 (2) |
O3—Na3—O5 | 94.14 (7) | C8—C9—C10 | 117.4 (2) |
O6iii—Na3—O5 | 152.25 (7) | C9—C10—H10A | 109.5 |
O5iii—Na3—O2 | 157.25 (8) | C9—C10—H10B | 109.5 |
O3—Na3—O2 | 83.53 (7) | H10A—C10—H10B | 109.5 |
O6iii—Na3—O2 | 80.21 (7) | C9—C10—H10C | 109.5 |
O5—Na3—O2 | 110.62 (7) | H10A—C10—H10C | 109.5 |
C2—O1—Na1 | 117.72 (16) | H10B—C10—H10C | 109.5 |
C2—O1—Na2 | 147.40 (16) | C12—C11—H11A | 109.5 |
Na1—O1—Na2 | 91.34 (7) | C12—C11—H11B | 109.5 |
C2—O1—Na2i | 100.23 (15) | H11A—C11—H11B | 109.5 |
Na1—O1—Na2i | 89.38 (7) | C12—C11—H11C | 109.5 |
Na2—O1—Na2i | 94.15 (7) | H11A—C11—H11C | 109.5 |
C4—O2—Na3 | 146.57 (16) | H11B—C11—H11C | 109.5 |
C4—O2—Na1 | 117.62 (15) | O5—C12—C13 | 125.9 (2) |
Na3—O2—Na1 | 93.56 (7) | O5—C12—C11 | 116.9 (2) |
C4—O2—Na2i | 99.74 (15) | C13—C12—C11 | 117.2 (2) |
Na3—O2—Na2i | 92.98 (7) | C14—C13—C12 | 126.8 (2) |
Na1—O2—Na2i | 87.49 (7) | C14—C13—H13 | 116.6 |
C7—O3—Na1 | 124.09 (16) | C12—C13—H13 | 116.6 |
C7—O3—Na3 | 137.56 (17) | O6—C14—C13 | 125.5 (2) |
Na1—O3—Na3 | 97.83 (7) | O6—C14—C15 | 116.2 (2) |
C9—O4—Na1 | 124.35 (16) | C13—C14—C15 | 118.3 (2) |
C9—O4—Na2 | 143.65 (18) | C14—C15—H15A | 109.5 |
Na1—O4—Na2 | 90.92 (7) | C14—C15—H15B | 109.5 |
C12—O5—Na3iii | 131.51 (16) | H15A—C15—H15B | 109.5 |
C12—O5—Na3 | 127.67 (15) | C14—C15—H15C | 109.5 |
Na3iii—O5—Na3 | 94.80 (7) | H15A—C15—H15C | 109.5 |
C14—O6—Na2iv | 126.36 (16) | H15B—C15—H15C | 109.5 |
C14—O6—Na3iii | 130.94 (16) | N1—C16—C17 | 123.9 (3) |
Na2iv—O6—Na3iii | 98.88 (7) | N1—C16—H16 | 118.1 |
C20—N1—C16 | 116.4 (2) | C17—C16—H16 | 118.1 |
C20—N1—Na1 | 118.33 (19) | C16—C17—C18 | 118.7 (3) |
C16—N1—Na1 | 124.82 (18) | C16—C17—H17 | 120.7 |
C2—C1—H1A | 109.5 | C18—C17—H17 | 120.7 |
C2—C1—H1B | 109.5 | C19—C18—C17 | 118.7 (3) |
H1A—C1—H1B | 109.5 | C19—C18—H18 | 120.6 |
C2—C1—H1C | 109.5 | C17—C18—H18 | 120.6 |
H1A—C1—H1C | 109.5 | C18—C19—C20 | 118.7 (3) |
H1B—C1—H1C | 109.5 | C18—C19—H19 | 120.6 |
O1—C2—C3 | 124.5 (2) | C20—C19—H19 | 120.6 |
O1—C2—C1 | 116.6 (2) | N1—C20—C19 | 123.6 (3) |
C3—C2—C1 | 118.9 (2) | N1—C20—H20 | 118.2 |
C2—C3—C4 | 125.7 (2) | C19—C20—H20 | 118.2 |
C2—C3—H3 | 117.1 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y, z−1; (iii) −x+1, −y, −z+2; (iv) x, y, z+1. |