The Na—O bond in sodium fenamate

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.

Computing details

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).

(I)

Crystal data

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) Å^3	Block, colourless
Z = 4	0.75 × 0.69 × 0.44 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.066	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.181	w = 1/[σ^2(Fo^2) + (0.1355P)^2 + 0.2705P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Na—O2W^i	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—O1W^ii	2.4559 (19)	C9—C10	1.374 (3)
Na—Na^i	3.533 (2)	C9—H9	0.9300
Na—Na^ii	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—Na^ii	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—Na^i	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)
O2W^i—Na—O1W	103.43 (7)	C5—C4—H4	119.5
O2W^i—Na—O2W	83.76 (7)	C3—C4—H4	119.5
O1W—Na—O2W	99.36 (7)	C4—C5—C6	120.48 (19)
O2W^i—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)
O2W^i—Na—O1W^ii	96.53 (7)	C7—C6—H6	120.3
O1W—Na—O1W^ii	81.81 (6)	C5—C6—H6	120.3
O2W—Na—O1W^ii	178.71 (6)	C6—C7—C2	122.04 (19)
O1—Na—O1W^ii	88.42 (6)	C6—C7—H7	119.0
O2W^i—Na—Na^i	42.25 (4)	C2—C7—H7	119.0
O1W—Na—Na^i	105.35 (6)	C13—C8—C9	118.61 (19)
O2W—Na—Na^i	41.51 (4)	C13—C8—N1	122.21 (19)
O1—Na—Na^i	108.25 (5)	C9—C8—N1	119.00 (19)
O1W^ii—Na—Na^i	138.77 (6)	C10—C9—C8	120.5 (2)
O2W^i—Na—Na^ii	103.15 (6)	C10—C9—H9	119.7
O1W—Na—Na^ii	41.81 (4)	C8—C9—H9	119.7
O2W—Na—Na^ii	141.17 (6)	C9—C10—C11	120.6 (2)
O1—Na—Na^ii	117.95 (5)	C9—C10—H10	119.7
O1W^ii—Na—Na^ii	39.99 (4)	C11—C10—H10	119.7
Na^i—Na—Na^ii	132.73 (5)	C12—C11—C10	119.3 (2)
O2W^i—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
O1W^ii—Na—H2W1	159.3	C13—C12—H12	119.7
Na^i—Na—H2W1	55.3	C12—C13—C8	120.4 (2)
Na^ii—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—Na^ii	98.19 (6)
C3—N1—H1N	114 (2)	Na—O1W—H1W1	108.4
C8—N1—H1N	119 (2)	Na^ii—O1W—H1W1	99.1
O2—C1—O1	122.33 (16)	Na—O1W—H1W2	121.4
O2—C1—C2	118.81 (16)	Na^ii—O1W—H1W2	122.2
O1—C1—C2	118.83 (15)	H1W1—O1W—H1W2	105.1
C7—C2—C3	118.37 (17)	Na^i—O2W—Na	96.24 (7)
C7—C2—C1	118.87 (17)	Na^i—O2W—H2W1	127.6
C3—C2—C1	122.71 (15)	Na—O2W—H2W1	92.1
N1—C3—C4	120.47 (18)	Na^i—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)

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···O3W^i	0.86	1.91	2.753 (2)	167
O1W—H1W2···O1^iii	0.86	1.98	2.833 (2)	178
O2W—H2W2···O3W^iii	0.86	1.93	2.779 (2)	166
O3W—H3W1···O2	0.86	1.99	2.801 (2)	156
O3W—H3W2···O1^iv	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.