The sodium chloride complex catena-poly[[{μ3-2-[bis­(2-hy­droxy­eth­yl)amino]­ethan-1-ol}sodium] chloride], N(CH2CH2OH)3·NaCl

Krabbe, C.; Gock, V.; Lutter, M.; Jurkschat, K.

doi:10.1107/S2414314619002384

metal-organic compounds

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ISSN: 2414-3146

Volume 4| Part 2| February 2019| x190238

https://doi.org/10.1107/S2414314619002384

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The sodium chloride complex catena-poly[[{μ₃-2-[bis(2-hydroxyethyl)amino]ethan-1-ol}sodium] chloride], N(CH₂CH₂OH)₃·NaCl

Christina Krabbe,^a Vinusuya Gock,^a Michael Lutter ^a and Klaus Jurkschat ^a ^*

^aLehrstuhl für Anorganische Chemie II, Technische Universität Dortmund, 44221 Dortmund, Germany
^*Correspondence e-mail: klaus.jurkschat@tu-dortmund.de

Edited by M. Weil, Vienna University of Technology, Austria (Received 30 December 2018; accepted 15 February 2019; online 22 February 2019)

The reaction of sodium chloride with 2-[bis(2-hydroxyethyl)amino]ethan-1-ol results in the formation of the title salt {[Na{N(CH₂CH₂OH)₃}]Cl}_n. The polymeric structure is characterized by a sodium cation coordinated by one nitrogen and five oxygen atoms in a distorted octahedral environment. The resulting one-dimensional {—O—Na—O—Na—O}— coordination polymer extends parallel to [010] and is connected through the chloride counter-anion via O—H⋯Cl hydrogen bonding, giving rise to a two-dimensional supramolecular structure parallel to (001).

Keywords: crystal structure; sodium chloride; amino alcohol; hydrogen bridge; graph-set analysis.

CCDC reference: 1897488

Structure description

In the context of our long-standing focus on tin derivatives of aminoalcohols, as for instance stannatranes (Glowacki et al., 2016 , 2017 ; Zöller et al., 2011 , 2012 ; Zöller & Jurkschat, 2013 ), we are also interested in the structures of selected starting materials such as salt complexes of the amino alcohol N(CH₂CH₂OH)₃. Sodium complexes of this alcohol with iodide (Voegele et al., 1974 ) and perchlorate (Naiini et al., 1994 ) counter-anions have been reported previously. In both these molecular structures, the three alcohol functional groups of one molecule coordinate the sodium cation in addition to the nitrogen atom. However, the title compound (Fig. 1) shows another coordination pattern. The sodium cation Na1 is six-coordinated by N1, O3, O5 of one molecule and by O1A, O2A and O3B of symmetry-related molecules at distances of 2.533 (3), 2.495 (3), 2.438 (3), 2.389 (3), 2.355 (4), and 2.463 (3) Å, respectively [Symmetry code: (A) 1 − x, y − $[{1\over 2}]$ , 1 − z. (B) 1 − x, y + $[{1\over 2}]$ , 1 − z.]. The sodium cation exhibits a distorted octahedral environment with O3, O5, O5A and O3B occupying the equatorial positions, and with N1 and O1A axial. The distortion from the ideal octahedral environment is expressed by the trans angles [N1—Na1—O2A = 141.31 (12)°; O1—Na1—O1A = 165.04 (12)°; O3—Na1—O3B = 167.27 (11)°] deviating clearly from 180°. As a result of this coordination pattern, a one-dimensional polymer is formed along [010].

Figure 1
The crystal structure of [Na(N(CH₂CH₂OH)₃)]Cl, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms bonded to carbon atoms have been omitted for clarity. Atoms Cl1A and Cl1B are not shown because they are located behind and in front of the bc plane. Hydrogen bonds are drawn as dashed lines. [Symmetry codes: (A) 1 − x, y − $[{1\over 2}]$ , 1 − z. (B) 1 − x, y + $[{1\over 2}]$ , 1 − z.]

In the crystal structure three hydrogen bonds between chloride anions and oxygen atoms of the alcohol functional groups are present (Table 1, Fig. 1). A graph-set analysis according to Etter and Bernstein (Bernstein et al., 1990 , 1995 ; Etter et al., 1990 ; Etter, 1990 , 1991 ) gives the unitary graph set N₁ = DDD. These hydrogen bonds create a two-dimensional supramolecular network structure extending parallel to (001).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯Cl1	0.86 (4)	2.21 (4)	3.061 (3)	169 (4)
O2—H2⋯Cl1ⁱ	0.72 (5)	2.44 (5)	3.141 (4)	165 (6)
O3—H3⋯Cl1ⁱⁱ	0.83 (3)	2.33 (3)	3.124 (3)	161 (3)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+1]$ .

Synthesis and crystallization

After addition of N(CH₂CH₂OH)₃ (3.14 g, 0.02 mmol) to a solution of sodium chloride (2.46 g, 0.04 mmol) in THF, two thirds of the solvent were distilled off. The title compound crystallized from the solution as colourless plate-shaped crystals.

¹H-NMR: (400.13 MHz, DMSO-d₆) δ 2.57 (s, ν_1/2 = 8 Hz, 6 H, NCH₂), 3.42 (s, ν_1/2 = 8 Hz, 6 H, OCH₂), 4.38 (s, ν_1/2 = 8 Hz, 3 H, OH).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. For the X-ray data collection, a strategy for centrosymmetric space groups was chosen. As a result of the oxygen atoms O1, O3, and O5 being crystallographically non-equivalent, the N1 atom is a stereogenic center, and thus the compound crystallizes in a non-centrosymmetric space-group type. Consequently, the number of collected data is less than expected for this symmetry and probably explains the goodness-of-fit parameter lying outside the usual range. However, the absolute structure was determined correctly (Table 2).

Table 2
Experimental details

Crystal data
Chemical formula	[Na(C₆H₁₅NO₃)]·Cl
M_r	207.63
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	173
a, b, c (Å)	7.7981 (10), 7.2249 (8), 8.9956 (11)
β (°)	110.380 (14)
V (Å³)	475.09 (11)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.42
Crystal size (mm)	0.32 × 0.06 × 0.03

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ )
T_min, T_max	0.903, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	3110, 1719, 1201
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.043, 0.70
No. of reflections	1719
No. of parameters	121
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.18
Absolute structure	Flack x determined using 408 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	−0.07 (7)
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ), SHELXT2014 (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1897488

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619002384/wm4096sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619002384/wm4096Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

catena-Poly[[{µ₃-2-[bis(2-hydroxyethyl)amino]ethan-1-ol}sodium] chloride] top

Crystal data top

[Na(C₆H₁₅NO₃)]·Cl	F(000) = 220
M_r = 207.63	D_x = 1.451 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.7981 (10) Å	Cell parameters from 1217 reflections
b = 7.2249 (8) Å	θ = 2.4–28.9°
c = 8.9956 (11) Å	µ = 0.42 mm⁻¹
β = 110.380 (14)°	T = 173 K
V = 475.09 (11) Å³	Column, colourless
Z = 2	0.32 × 0.06 × 0.03 mm

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	1719 independent reflections
Graphite monochromator	1201 reflections with I > 2σ(I)
Detector resolution: 16.0560 pixels mm^-1	R_int = 0.035
ω und ψ scan	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −4→9
T_min = 0.903, T_max = 1.000	k = −8→8
3110 measured reflections	l = −10→10

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.032	w = 1/[σ²(F_o²) + (0.0132P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.043	(Δ/σ)_max < 0.001
S = 0.70	Δρ_max = 0.20 e Å⁻³
1719 reflections	Δρ_min = −0.18 e Å⁻³
121 parameters	Absolute structure: Flack x determined using 408 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: −0.07 (7)

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.

Refinement. The hydrogen atoms of the OH groups were located in a difference Fourier map and were refined with U_iso(H) = 1.2U_eq(O).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.11499 (13)	0.52160 (16)	0.72753 (10)	0.0212 (3)
Na1	0.4707 (2)	0.2903 (2)	0.49696 (18)	0.0163 (4)
N1	0.3494 (4)	0.3861 (4)	0.2080 (3)	0.0125 (8)
O1	0.2902 (4)	0.5714 (4)	0.4739 (3)	0.0169 (7)
H1	0.237 (5)	0.574 (6)	0.543 (4)	0.033 (14)*
O2	0.6300 (4)	0.6951 (4)	0.2967 (3)	0.0222 (8)
H2	0.697 (6)	0.756 (8)	0.285 (5)	0.05 (2)*
O3	0.3064 (3)	0.0176 (5)	0.3419 (3)	0.0170 (6)
H3	0.202 (4)	0.010 (7)	0.347 (4)	0.021 (12)*
C21	0.6635 (5)	0.5139 (7)	0.2528 (4)	0.0194 (10)
H21A	0.713380	0.439122	0.347642	0.023*
H21B	0.754537	0.520099	0.201930	0.023*
C22	0.4935 (5)	0.4210 (5)	0.1415 (4)	0.0180 (11)
H22A	0.443202	0.497838	0.047906	0.022*
H22B	0.528554	0.303870	0.107800	0.022*
C11	0.1473 (5)	0.5556 (6)	0.3212 (4)	0.0191 (10)
H11A	0.063574	0.659234	0.303972	0.023*
H11B	0.078900	0.442075	0.315703	0.023*
C12	0.2370 (4)	0.5544 (6)	0.1967 (4)	0.0141 (10)
H12A	0.143227	0.560173	0.092254	0.017*
H12B	0.313816	0.663093	0.209870	0.017*
C31	0.3015 (5)	0.0465 (6)	0.1825 (4)	0.0179 (10)
H31A	0.224855	−0.047398	0.113926	0.021*
H31B	0.423976	0.033351	0.179493	0.021*
C32	0.2286 (5)	0.2344 (5)	0.1218 (4)	0.0155 (10)
H32A	0.213121	0.242377	0.010263	0.019*
H32B	0.109213	0.249789	0.131188	0.019*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0187 (6)	0.0235 (6)	0.0250 (5)	0.0026 (6)	0.0121 (4)	0.0014 (6)
Na1	0.0148 (10)	0.0159 (9)	0.0183 (7)	0.0024 (8)	0.0057 (7)	0.0008 (7)
N1	0.0098 (19)	0.0107 (19)	0.0178 (18)	−0.0020 (14)	0.0056 (15)	0.0012 (14)
O1	0.0136 (16)	0.0215 (19)	0.0169 (14)	0.0010 (13)	0.0069 (14)	−0.0008 (12)
O2	0.021 (2)	0.019 (2)	0.0310 (18)	−0.0079 (15)	0.0150 (16)	−0.0067 (15)
O3	0.0136 (16)	0.0200 (16)	0.0171 (13)	−0.0014 (18)	0.0050 (12)	0.0013 (16)
C21	0.016 (2)	0.023 (3)	0.022 (2)	0.002 (3)	0.0100 (18)	0.000 (3)
C22	0.021 (3)	0.012 (3)	0.024 (2)	−0.001 (2)	0.011 (2)	0.0001 (18)
C11	0.013 (2)	0.017 (3)	0.025 (2)	−0.001 (2)	0.0027 (18)	−0.002 (2)
C12	0.010 (2)	0.010 (3)	0.0174 (19)	0.003 (2)	−0.0008 (16)	0.003 (2)
C31	0.019 (2)	0.020 (3)	0.0165 (19)	−0.004 (2)	0.0090 (17)	−0.006 (2)
C32	0.017 (2)	0.014 (3)	0.015 (2)	−0.0020 (18)	0.0048 (19)	0.0006 (17)

Geometric parameters (Å, º) top

Na1—O2ⁱ	2.355 (4)	C21—C22	1.512 (5)
Na1—O1ⁱ	2.389 (3)	C21—H21A	0.9700
Na1—O1	2.438 (3)	C21—H21B	0.9700
Na1—O3ⁱⁱ	2.463 (3)	C22—H22A	0.9700
Na1—O3	2.495 (3)	C22—H22B	0.9700
Na1—N1	2.533 (3)	C11—C12	1.513 (4)
Na1—C11	3.123 (4)	C11—H11A	0.9700
N1—C22	1.467 (4)	C11—H11B	0.9700
N1—C32	1.477 (4)	C12—H12A	0.9700
N1—C12	1.481 (4)	C12—H12B	0.9700
O1—C11	1.441 (4)	C31—C32	1.499 (5)
O1—H1	0.86 (4)	C31—H31A	0.9700
O2—C21	1.418 (5)	C31—H31B	0.9700
O2—H2	0.72 (5)	C32—H32A	0.9700
O3—C31	1.436 (4)	C32—H32B	0.9700
O3—H3	0.83 (3)

O2ⁱ—Na1—O1ⁱ	100.48 (12)	Na1—O3—H3	110 (3)
O2ⁱ—Na1—O1	88.25 (12)	O2—C21—C22	113.0 (3)
O1ⁱ—Na1—O1	165.04 (12)	O2—C21—H21A	109.0
O2ⁱ—Na1—O3ⁱⁱ	95.27 (11)	C22—C21—H21A	109.0
O1ⁱ—Na1—O3ⁱⁱ	90.72 (10)	O2—C21—H21B	109.0
O1—Na1—O3ⁱⁱ	76.30 (10)	C22—C21—H21B	109.0
O2ⁱ—Na1—O3	87.85 (11)	H21A—C21—H21B	107.8
O1ⁱ—Na1—O3	76.57 (10)	N1—C22—C21	115.2 (3)
O1—Na1—O3	116.20 (10)	N1—C22—H22A	108.5
O3ⁱⁱ—Na1—O3	167.27 (11)	C21—C22—H22A	108.5
O2ⁱ—Na1—N1	141.31 (12)	N1—C22—H22B	108.5
O1ⁱ—Na1—N1	106.95 (12)	C21—C22—H22B	108.5
O1—Na1—N1	71.76 (11)	H22A—C22—H22B	107.5
O3ⁱⁱ—Na1—N1	110.88 (11)	O1—C11—C12	107.6 (3)
O3—Na1—N1	72.95 (10)	O1—C11—Na1	49.17 (18)
O2ⁱ—Na1—C11	98.40 (12)	C12—C11—Na1	82.6 (2)
O1ⁱ—Na1—C11	157.45 (11)	O1—C11—H11A	110.2
O1—Na1—C11	26.55 (9)	C12—C11—H11A	110.2
O3ⁱⁱ—Na1—C11	99.73 (11)	Na1—C11—H11A	159.2
O3—Na1—C11	91.99 (11)	O1—C11—H11B	110.2
N1—Na1—C11	50.65 (10)	C12—C11—H11B	110.2
C22—N1—C32	110.7 (3)	Na1—C11—H11B	80.8
C22—N1—C12	110.5 (3)	H11A—C11—H11B	108.5
C32—N1—C12	108.6 (3)	N1—C12—C11	111.7 (3)
C22—N1—Na1	113.6 (2)	N1—C12—H12A	109.3
C32—N1—Na1	106.1 (2)	C11—C12—H12A	109.3
C12—N1—Na1	107.1 (2)	N1—C12—H12B	109.3
C11—O1—Na1ⁱⁱ	118.2 (2)	C11—C12—H12B	109.3
C11—O1—Na1	104.3 (2)	H12A—C12—H12B	107.9
Na1ⁱⁱ—O1—Na1	97.85 (10)	O3—C31—C32	111.7 (3)
C11—O1—H1	106 (2)	O3—C31—H31A	109.3
Na1ⁱⁱ—O1—H1	118 (3)	C32—C31—H31A	109.3
Na1—O1—H1	111 (3)	O3—C31—H31B	109.3
C21—O2—Na1ⁱⁱ	129.3 (3)	C32—C31—H31B	109.3
C21—O2—H2	108 (4)	H31A—C31—H31B	107.9
Na1ⁱⁱ—O2—H2	113 (4)	N1—C32—C31	112.9 (3)
C31—O3—Na1ⁱ	116.9 (2)	N1—C32—H32A	109.0
C31—O3—Na1	105.8 (3)	C31—C32—H32A	109.0
Na1ⁱ—O3—Na1	94.46 (8)	N1—C32—H32B	109.0
C31—O3—H3	112 (2)	C31—C32—H32B	109.0
Na1ⁱ—O3—H3	115 (3)	H32A—C32—H32B	107.8

Na1ⁱⁱ—O2—C21—C22	85.8 (3)	Na1—N1—C12—C11	−30.7 (3)
C32—N1—C22—C21	−156.9 (3)	O1—C11—C12—N1	66.4 (4)
C12—N1—C22—C21	82.8 (4)	Na1—C11—C12—N1	23.5 (3)
Na1—N1—C22—C21	−37.7 (4)	Na1ⁱ—O3—C31—C32	−155.0 (2)
O2—C21—C22—N1	−64.2 (4)	Na1—O3—C31—C32	−51.4 (3)
Na1ⁱⁱ—O1—C11—C12	44.2 (4)	C22—N1—C32—C31	84.7 (4)
Na1—O1—C11—C12	−63.1 (3)	C12—N1—C32—C31	−153.9 (3)
Na1ⁱⁱ—O1—C11—Na1	107.2 (2)	Na1—N1—C32—C31	−39.0 (3)
C22—N1—C12—C11	−155.0 (3)	O3—C31—C32—N1	65.8 (4)
C32—N1—C12—C11	83.5 (3)

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) −x+1, y+1/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl1	0.86 (4)	2.21 (4)	3.061 (3)	169 (4)
O2—H2···Cl1ⁱⁱ	0.72 (5)	2.44 (5)	3.141 (4)	165 (6)
O3—H3···Cl1ⁱⁱⁱ	0.83 (3)	2.33 (3)	3.124 (3)	161 (3)

Symmetry codes: (ii) −x+1, y+1/2, −z+1; (iii) −x, y−1/2, −z+1.

Acknowledgements

We acknowledge financial support by the Deutsche Forschungsgemeinschaft and Technische Universität Dortmund within the funding programme Open Access Publishing.

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