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The one-dimensional polymeric structure of sodium diaquafenamate–water (1/1) was studied by X-ray diffraction. The sodium cation is coordinated to one oxygen atom of the carboxylate group and to four water oxygen atoms. To characterize the Na—O bonds, the quantum theory of atoms in molecules (QTAIM) and noncovalent interaction (NCI) approaches have been used. Both methods confirmed that the Na—O bonds are very weak, comparable with the weak N—H
O intramolecular hydrogen bond. The polymeric structure is stabilized by the interaction of the sodium cation with the surrounding water molecules.
Supporting information
CCDC reference: 1936254
Data collection: 'CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)'; cell refinement: 'CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)'; data reduction: 'CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)'; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014).
Crystal data top
C13H14NNaO4·H2O | F(000) = 608 |
Mr = 289.26 | Dx = 1.341 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.5418 Å |
a = 6.059 (3) Å | Cell parameters from 3722 reflections |
b = 37.243 (7) Å | θ = 2.4–68.0° |
c = 6.577 (3) Å | µ = 1.12 mm−1 |
β = 105.12 (3)° | T = 293 K |
V = 1432.8 (10) Å3 | Block, colourless |
Z = 4 | 0.75 × 0.69 × 0.44 mm |
Data collection top
Xcalibur with CCD Onyx detector diffractometer | 2331 reflections with I > 2σ(I) |
Radiation source: Enhance (Cu) X-ray Source | Rint = 0.032 |
ω scans | θmax = 68.1°, θmin = 2.4° |
Absorption correction: analytical CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) | h = −4→7 |
Tmin = 0.918, Tmax = 0.952 | k = −44→35 |
4755 measured reflections | l = −7→7 |
2603 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.066 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.181 | w = 1/[σ2(Fo2) + (0.1355P)2 + 0.2705P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
2603 reflections | Δρmax = 0.31 e Å−3 |
184 parameters | Δρmin = −0.47 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Na | 0.57350 (12) | 0.98451 (2) | 0.76298 (11) | 0.0382 (3) | |
O1 | 0.8816 (2) | 0.94185 (4) | 0.8034 (2) | 0.0359 (4) | |
O2 | 0.7285 (2) | 0.91140 (4) | 0.5121 (2) | 0.0388 (4) | |
N1 | 0.9154 (3) | 0.85053 (6) | 0.4391 (3) | 0.0493 (5) | |
H1N | 0.796 (5) | 0.8628 (9) | 0.432 (5) | 0.059* | |
C1 | 0.8858 (3) | 0.91630 (5) | 0.6772 (3) | 0.0280 (4) | |
C2 | 1.0883 (3) | 0.89173 (5) | 0.7230 (3) | 0.0298 (4) | |
C3 | 1.1010 (3) | 0.86115 (5) | 0.5984 (3) | 0.0337 (4) | |
C4 | 1.3041 (4) | 0.84086 (6) | 0.6461 (3) | 0.0419 (5) | |
H4 | 1.3148 | 0.8207 | 0.5655 | 0.050* | |
C5 | 1.4874 (3) | 0.85035 (6) | 0.8105 (4) | 0.0458 (5) | |
H5 | 1.6213 | 0.8369 | 0.8376 | 0.055* | |
C6 | 1.4736 (3) | 0.87962 (6) | 0.9350 (3) | 0.0446 (5) | |
H6 | 1.5963 | 0.8856 | 1.0478 | 0.054* | |
C7 | 1.2765 (3) | 0.89989 (5) | 0.8909 (3) | 0.0380 (5) | |
H7 | 1.2684 | 0.9196 | 0.9754 | 0.046* | |
C8 | 0.9074 (3) | 0.82217 (5) | 0.2970 (3) | 0.0352 (4) | |
C9 | 0.7318 (4) | 0.79716 (6) | 0.2690 (3) | 0.0444 (5) | |
H9 | 0.6290 | 0.7984 | 0.3520 | 0.053* | |
C10 | 0.7088 (4) | 0.77064 (6) | 0.1198 (4) | 0.0523 (6) | |
H10 | 0.5895 | 0.7542 | 0.1014 | 0.063* | |
C11 | 0.8611 (4) | 0.76813 (6) | −0.0033 (4) | 0.0515 (6) | |
H11 | 0.8457 | 0.7500 | −0.1034 | 0.062* | |
C12 | 1.0362 (4) | 0.79271 (7) | 0.0238 (4) | 0.0502 (6) | |
H12 | 1.1398 | 0.7911 | −0.0582 | 0.060* | |
C13 | 1.0592 (3) | 0.81967 (6) | 0.1715 (4) | 0.0436 (5) | |
H13 | 1.1770 | 0.8363 | 0.1873 | 0.052* | |
O1W | 0.2411 (2) | 0.99281 (4) | 0.8830 (2) | 0.0409 (4) | |
H1W1 | 0.1749 | 1.0122 | 0.8282 | 0.061* | |
H1W2 | 0.1348 | 0.9769 | 0.8613 | 0.061* | |
O2W | 0.4009 (2) | 0.96176 (4) | 0.4184 (2) | 0.0425 (4) | |
H2W1 | 0.4923 | 0.9437 | 0.4368 | 0.064* | |
H2W2 | 0.2669 | 0.9524 | 0.3744 | 0.064* | |
O3W | 0.9539 (3) | 0.94091 (5) | 0.2297 (2) | 0.0449 (4) | |
H3W1 | 0.8885 | 0.9262 | 0.2962 | 0.067* | |
H3W2 | 0.9329 | 0.9318 | 0.1062 | 0.067* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Na | 0.0323 (4) | 0.0503 (5) | 0.0303 (5) | 0.0050 (3) | 0.0048 (3) | −0.0040 (3) |
O1 | 0.0355 (7) | 0.0389 (8) | 0.0310 (7) | 0.0021 (5) | 0.0047 (5) | −0.0060 (5) |
O2 | 0.0308 (7) | 0.0468 (8) | 0.0329 (7) | 0.0071 (5) | −0.0021 (5) | −0.0072 (6) |
N1 | 0.0325 (9) | 0.0545 (11) | 0.0527 (11) | 0.0089 (7) | −0.0038 (8) | −0.0246 (9) |
C1 | 0.0278 (8) | 0.0327 (9) | 0.0236 (8) | −0.0021 (6) | 0.0069 (6) | 0.0018 (6) |
C2 | 0.0272 (8) | 0.0342 (9) | 0.0264 (8) | −0.0002 (7) | 0.0042 (7) | 0.0030 (7) |
C3 | 0.0290 (9) | 0.0382 (10) | 0.0312 (9) | −0.0006 (7) | 0.0029 (7) | −0.0015 (7) |
C4 | 0.0370 (10) | 0.0412 (11) | 0.0436 (11) | 0.0090 (8) | 0.0031 (8) | −0.0028 (8) |
C5 | 0.0315 (9) | 0.0518 (13) | 0.0487 (12) | 0.0100 (8) | 0.0009 (9) | 0.0082 (9) |
C6 | 0.0313 (9) | 0.0548 (13) | 0.0384 (10) | 0.0007 (8) | −0.0076 (8) | 0.0028 (9) |
C7 | 0.0388 (10) | 0.0391 (10) | 0.0306 (9) | −0.0017 (8) | −0.0007 (8) | 0.0002 (7) |
C8 | 0.0326 (9) | 0.0350 (10) | 0.0342 (10) | 0.0032 (7) | 0.0019 (7) | −0.0040 (7) |
C9 | 0.0421 (11) | 0.0497 (12) | 0.0429 (11) | −0.0059 (9) | 0.0139 (8) | −0.0057 (9) |
C10 | 0.0570 (13) | 0.0403 (12) | 0.0572 (14) | −0.0107 (9) | 0.0109 (11) | −0.0082 (10) |
C11 | 0.0618 (14) | 0.0439 (12) | 0.0452 (12) | 0.0100 (10) | 0.0072 (10) | −0.0125 (9) |
C12 | 0.0484 (12) | 0.0618 (14) | 0.0429 (11) | 0.0120 (10) | 0.0161 (10) | −0.0053 (10) |
C13 | 0.0364 (10) | 0.0459 (11) | 0.0481 (12) | −0.0017 (8) | 0.0103 (8) | −0.0006 (9) |
O1W | 0.0314 (7) | 0.0460 (8) | 0.0435 (8) | −0.0032 (5) | 0.0063 (6) | −0.0058 (6) |
O2W | 0.0343 (7) | 0.0439 (8) | 0.0434 (8) | 0.0018 (5) | −0.0004 (6) | −0.0034 (6) |
O3W | 0.0426 (8) | 0.0596 (9) | 0.0301 (7) | −0.0075 (6) | 0.0052 (6) | −0.0010 (6) |
Geometric parameters (Å, º) top
Na—O2Wi | 2.3553 (18) | C6—H6 | 0.9300 |
Na—O1W | 2.3675 (19) | C7—H7 | 0.9300 |
Na—O2W | 2.3898 (19) | C8—C13 | 1.389 (3) |
Na—O1 | 2.4129 (18) | C8—C9 | 1.390 (3) |
Na—O1Wii | 2.4559 (19) | C9—C10 | 1.374 (3) |
Na—Nai | 3.533 (2) | C9—H9 | 0.9300 |
Na—Naii | 3.646 (2) | C10—C11 | 1.380 (4) |
Na—H2W1 | 2.5696 | C10—H10 | 0.9300 |
O1—C1 | 1.267 (2) | C11—C12 | 1.377 (4) |
O2—C1 | 1.257 (2) | C11—H11 | 0.9300 |
N1—C3 | 1.380 (3) | C12—C13 | 1.379 (3) |
N1—C8 | 1.403 (3) | C12—H12 | 0.9300 |
N1—H1N | 0.85 (3) | C13—H13 | 0.9300 |
C1—C2 | 1.497 (2) | O1W—Naii | 2.4559 (19) |
C2—C7 | 1.398 (3) | O1W—H1W1 | 0.8572 |
C2—C3 | 1.417 (3) | O1W—H1W2 | 0.8582 |
C3—C4 | 1.408 (3) | O2W—Nai | 2.3553 (19) |
C4—C5 | 1.379 (3) | O2W—H2W1 | 0.8593 |
C4—H4 | 0.9300 | O2W—H2W2 | 0.8611 |
C5—C6 | 1.379 (3) | O3W—H3W1 | 0.8590 |
C5—H5 | 0.9300 | O3W—H3W2 | 0.8587 |
C6—C7 | 1.379 (3) | | |
| | | |
O2Wi—Na—O1W | 103.43 (7) | C5—C4—H4 | 119.5 |
O2Wi—Na—O2W | 83.76 (7) | C3—C4—H4 | 119.5 |
O1W—Na—O2W | 99.36 (7) | C4—C5—C6 | 120.48 (19) |
O2Wi—Na—O1 | 117.64 (6) | C4—C5—H5 | 119.8 |
O1W—Na—O1 | 138.62 (7) | C6—C5—H5 | 119.8 |
O2W—Na—O1 | 90.33 (6) | C7—C6—C5 | 119.42 (18) |
O2Wi—Na—O1Wii | 96.53 (7) | C7—C6—H6 | 120.3 |
O1W—Na—O1Wii | 81.81 (6) | C5—C6—H6 | 120.3 |
O2W—Na—O1Wii | 178.71 (6) | C6—C7—C2 | 122.04 (19) |
O1—Na—O1Wii | 88.42 (6) | C6—C7—H7 | 119.0 |
O2Wi—Na—Nai | 42.25 (4) | C2—C7—H7 | 119.0 |
O1W—Na—Nai | 105.35 (6) | C13—C8—C9 | 118.61 (19) |
O2W—Na—Nai | 41.51 (4) | C13—C8—N1 | 122.21 (19) |
O1—Na—Nai | 108.25 (5) | C9—C8—N1 | 119.00 (19) |
O1Wii—Na—Nai | 138.77 (6) | C10—C9—C8 | 120.5 (2) |
O2Wi—Na—Naii | 103.15 (6) | C10—C9—H9 | 119.7 |
O1W—Na—Naii | 41.81 (4) | C8—C9—H9 | 119.7 |
O2W—Na—Naii | 141.17 (6) | C9—C10—C11 | 120.6 (2) |
O1—Na—Naii | 117.95 (5) | C9—C10—H10 | 119.7 |
O1Wii—Na—Naii | 39.99 (4) | C11—C10—H10 | 119.7 |
Nai—Na—Naii | 132.73 (5) | C12—C11—C10 | 119.3 (2) |
O2Wi—Na—H2W1 | 95.9 | C12—C11—H11 | 120.3 |
O1W—Na—H2W1 | 111.2 | C10—C11—H11 | 120.3 |
O2W—Na—H2W1 | 19.5 | C11—C12—C13 | 120.5 (2) |
O1—Na—H2W1 | 71.1 | C11—C12—H12 | 119.7 |
O1Wii—Na—H2W1 | 159.3 | C13—C12—H12 | 119.7 |
Nai—Na—H2W1 | 55.3 | C12—C13—C8 | 120.4 (2) |
Naii—Na—H2W1 | 149.9 | C12—C13—H13 | 119.8 |
C1—O1—Na | 124.68 (11) | C8—C13—H13 | 119.8 |
C3—N1—C8 | 126.98 (18) | Na—O1W—Naii | 98.19 (6) |
C3—N1—H1N | 114 (2) | Na—O1W—H1W1 | 108.4 |
C8—N1—H1N | 119 (2) | Naii—O1W—H1W1 | 99.1 |
O2—C1—O1 | 122.33 (16) | Na—O1W—H1W2 | 121.4 |
O2—C1—C2 | 118.81 (16) | Naii—O1W—H1W2 | 122.2 |
O1—C1—C2 | 118.83 (15) | H1W1—O1W—H1W2 | 105.1 |
C7—C2—C3 | 118.37 (17) | Nai—O2W—Na | 96.24 (7) |
C7—C2—C1 | 118.87 (17) | Nai—O2W—H2W1 | 127.6 |
C3—C2—C1 | 122.71 (15) | Na—O2W—H2W1 | 92.1 |
N1—C3—C4 | 120.47 (18) | Nai—O2W—H2W2 | 110.8 |
N1—C3—C2 | 120.86 (17) | Na—O2W—H2W2 | 127.1 |
C4—C3—C2 | 118.61 (17) | H2W1—O2W—H2W2 | 104.3 |
C5—C4—C3 | 121.0 (2) | H3W1—O3W—H3W2 | 104.8 |
| | | |
Na—O1—C1—O2 | 2.2 (2) | C4—C5—C6—C7 | −1.5 (3) |
Na—O1—C1—C2 | −179.69 (11) | C5—C6—C7—C2 | 0.1 (3) |
O2—C1—C2—C7 | 171.67 (17) | C3—C2—C7—C6 | 1.4 (3) |
O1—C1—C2—C7 | −6.5 (2) | C1—C2—C7—C6 | −176.35 (18) |
O2—C1—C2—C3 | −6.0 (3) | C3—N1—C8—C13 | −55.3 (3) |
O1—C1—C2—C3 | 175.79 (17) | C3—N1—C8—C9 | 129.6 (2) |
C8—N1—C3—C4 | −6.4 (4) | C13—C8—C9—C10 | −0.2 (3) |
C8—N1—C3—C2 | 176.3 (2) | N1—C8—C9—C10 | 175.1 (2) |
C7—C2—C3—N1 | 175.91 (19) | C8—C9—C10—C11 | 0.7 (4) |
C1—C2—C3—N1 | −6.4 (3) | C9—C10—C11—C12 | −0.5 (4) |
C7—C2—C3—C4 | −1.5 (3) | C10—C11—C12—C13 | −0.3 (4) |
C1—C2—C3—C4 | 176.21 (18) | C11—C12—C13—C8 | 0.8 (3) |
N1—C3—C4—C5 | −177.3 (2) | C9—C8—C13—C12 | −0.5 (3) |
C2—C3—C4—C5 | 0.1 (3) | N1—C8—C13—C12 | −175.7 (2) |
C3—C4—C5—C6 | 1.4 (4) | | |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+2, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2 | 0.85 (3) | 1.96 (3) | 2.634 (2) | 136 (3) |
O1W—H1W1···O3Wi | 0.86 | 1.91 | 2.753 (2) | 167 |
O1W—H1W2···O1iii | 0.86 | 1.98 | 2.833 (2) | 178 |
O2W—H2W2···O3Wiii | 0.86 | 1.93 | 2.779 (2) | 166 |
O3W—H3W1···O2 | 0.86 | 1.99 | 2.801 (2) | 156 |
O3W—H3W2···O1iv | 0.86 | 1.97 | 2.722 (2) | 146 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (iii) x−1, y, z; (iv) x, y, z−1. |
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