Betaine (tri­methyl­ammonio­acetate) binary compound with sodium iodide

Nazarenko, A.Y.

doi:10.1107/S2414314618008647

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 6| June 2018| x180864

https://doi.org/10.1107/S2414314618008647

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Betaine (trimethylammonioacetate) binary compound with sodium iodide

Alexander Y. Nazarenko ^a ^*

^aChemistry Department, SUNY Buffalo State, 1300 Elmwood Ave, Buffalo, NY 14222, USA
^*Correspondence e-mail: nazareay@buffalostate.edu

Edited by R. J. Butcher, Howard University, USA (Received 23 May 2018; accepted 12 June 2018; online 15 June 2018)

In the title compound, catena-poly[[[bis[2-(trimethylazaniumyl)acetato-κO]sodium]-di-μ-aqua-[diaquasodium]-di-μ-aqua] diiodide], {[Na₂(C₅H₁₁NO₂)₂(H₂O)₆]I₂}_n, both Na⁺ ions have distorted octahedral environments (coordination number 6). The coordination polyhedra of the sodium ions are connected by common edges forming an infinite chain of ions along [100]. The chains and betaine zwitterions are assembled into infinitive layers via hydrogen bonds. These layers are connected via electrostatic attraction between iodide ions and positive trimethylazanium groups in the crystal.

Keywords: crystal structure; betaine; trimethylammonioacetate; sodium iodide.

CCDC reference: 1848958

Structure description

Betaines represent a wide class of zwitterionic compounds with an onium group that bears no hydrogen atoms and that is not adjacent to the anionic atom. The parent compound of the betaine class, trimethylammonioacetate (TMA), has a very rich crystal chemistry: the Cambridge Structural Database (CSD Version 5.39; Groom et al., 2016 ) contains 217 different structures of its compounds. There are several known crystal structures of TMA binary compounds with potassium iodide (HIPQIG; Andrade et al., 1999 ), rubidium iodide (NEMKIZ; Andrade et al., 2001 ), potassium bromide (WIQPUH01; Andrade et al., 2000 ) and sodium bromide (JAZNEE; Rodrigues et al., 2005 ). In a continuation of studies (Nazarenko, 2018 ) of zwitterionic binary compounds, an unreported structure of trimethylammonioacetate with sodium iodide is presented here.

The numbering scheme for the title compound is shown in Fig. 1. Both Na⁺ ions have distorted octahedral environments. The coordination sphere of Na1 (Table 1, Fig. 2) contains two pairs of bridging O atoms of water molecules (O1 and O6; O4 and O5) and two terminal water molecules (atoms O2 and O3). The coordination sphere of Na2 contains two anionic oxygen atoms of monodentate carboxylic groups (O7 and O9) and the same four bridging atoms (Table 1, Fig. 2).

Table 1
Selected bond lengths (Å)

Na1—O1	2.3733 (17)	Na2—O1ⁱⁱ	2.6120 (18)
Na1—O2	2.3842 (17)	Na2—O4	2.3944 (16)
Na1—O3	2.4650 (16)	Na2—O5	2.4697 (17)
Na1—O4	2.3926 (16)	Na2—O6	2.3412 (16)
Na1—O5	2.4926 (17)	Na2—O7	2.3937 (15)
Na1—O6ⁱ	2.4943 (17)	Na2—O9	2.3175 (16)
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

Figure 1
Numbering scheme for the title compound with 50% probability displacement ellipsoids.

Figure 2
Coordination polyhedra of the sodium ions.

The distribution of the Hirshfeld surface electrostatic potential of the zwitterion (Fig. 3) shows that only the area around the carboxyl oxygen atoms is negatively charged. The remaining Hirshfeld surface has positive electrostatic potential, which makes this area attractive for iodide anions.

Figure 3
Hirshfeld surface of the zwitterion with electrostatic potential plotted using CrystalExplorer17 (Turner et al., 2017

). Colour key: red – negative, blue – positive.

The coordination polyhedra of the sodium ions are connected by common edges (two pairs of bridging water molecules, O1 & O6 and O4 & O5), forming an infinite chain of ions along [100] (Fig. 4). In addition to Na—O interactions, this chain is supported by three hydrogen bonds (Table 2, Fig. 4): O1—H1B⋯O3, O4—H4B⋯O10, and O6—H6B⋯O10. The last two of these, connecting the anionic oxygen atom of the carboxylic group, are electrostatically enhanced. The chains are interconnected via five hydrogen bonds (O2—H2A⋯O9, O2—H2B⋯O8, O3—H3A⋯O10, O3—H3B⋯O8, O5—H5A⋯O8, see Table 2 and Fig. 5). Three more water hydrogen atoms are involved in hydrogen bonds with iodide ions (Table 2). The resulting network of hydrogen bonds forms layers in the (001) plane with iodide ions and trimethylammonium groups forming each side (Fig. 5). These layers are bound together via electrostatic interactions between the corresponding positive and negative ions; no short intralayer contacts are visible. A number of short intramolecular C—H⋯O contacts (Table 2) may play some auxiliary role in the conformation of the zwitterion. There are no suitable acceptor atoms for hydrogen atom H5B of a bridging water molecule; its orientation is an interplay between electrostatic attraction by neighboring iodide I1 and repulsion by both sodium ions and trimethylammonium group.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯I2ⁱ	0.74 (3)	3.03 (3)	3.7008 (17)	152 (3)
O1—H1B⋯O3ⁱ	0.78 (3)	2.01 (3)	2.781 (2)	172 (3)
O2—H2A⋯O9ⁱⁱⁱ	0.78 (3)	2.19 (3)	2.915 (2)	154 (3)
O2—H2B⋯O8ⁱⁱⁱ	0.76 (3)	2.00 (3)	2.7641 (19)	175 (3)
O3—H3A⋯O10ⁱⁱⁱ	0.80 (3)	1.99 (3)	2.772 (2)	169 (3)
O3—H3B⋯O8^iv	0.76 (3)	2.13 (3)	2.860 (2)	160 (3)
O4—H4A⋯I2	0.79 (3)	2.85 (3)	3.6300 (14)	172 (2)
O4—H4B⋯O10ⁱ	0.81 (3)	2.04 (3)	2.823 (2)	165 (2)
O5—H5A⋯O8^iv	0.79 (3)	1.97 (3)	2.7484 (19)	167 (3)
O6—H6A⋯I1ⁱⁱ	0.76 (3)	2.85 (3)	3.5864 (17)	165 (3)
O6—H6B⋯O7ⁱⁱ	0.79 (3)	2.05 (3)	2.829 (2)	168 (3)
C8—H8A⋯O10	0.98	2.33	2.976 (2)	122
C3—H3D⋯O8	0.98	2.39	2.999 (2)	120
C10—H10A⋯O10	0.98	2.34	2.994 (2)	123
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z; (iii) x+1, y+1, z; (iv) x, y+1, z.

Figure 4
The infinite chain of hydrated sodium ions along [100], viewed along [010].

Figure 5
Packing of the title compound, viewed along [100]. Sodium ions are green.

Known TMA binary compounds (Andrade et al., 1999, 2000, 2001; Rodrigues et al., 2005) show features similar to the current structure: an infinite chain of hydrated alkali metal cations and layers of trimethylammonium groups. However, in the current case the bridging in the cation chain is organized via water molecules [similar to the sodium iodide co-crystal in Nazarenko (2018)] and not by carboxylic groups. Sodium ions usually form stronger hydrates than rubidium and potassium ions; this observation can serve as a very simplistic explanation.

Synthesis and crystallization

Equimolar amounts of commercial betaine monohydrate were mixed with sodium iodide in aqueous ethanol, similar to the procedure described in Andrade et al. (1999, 2000, 2001); subsequent slow evaporation yielded crystals suitable for the single–crystal X-ray experiment.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3.

Table 3
Experimental details

Crystal data
Chemical formula	[Na₂(C₅H₁₁NO₂)₂(H₂O)₆]I₂
M_r	642.17
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	173
a, b, c (Å)	5.8131 (3), 7.6682 (4), 26.7168 (15)
α, β, γ (°)	90.221 (2), 91.168 (2), 91.440 (3)
V (Å³)	1190.29 (11)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	2.72
Crystal size (mm)	0.60 × 0.30 × 0.10

Data collection
Diffractometer	Bruker PHOTON-100 CMOS
Absorption correction	Numerical (SADABS; Krause et al., 2015 )
T_min, T_max	0.076, 0.252
No. of measured, independent and observed [I > 2σ(I)] reflections	49693, 8726, 7237
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.759

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.050, 1.15
No. of reflections	8726
No. of parameters	277
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.42
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ), CrystalExplorer17 (Turner et al., 2017 ) and VESTA (Momma & Izumi, 2008 ).

Structural data

CCDC reference: 1848958

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618008647/bv4018sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618008647/bv4018Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618008647/bv4018Isup3.cdx

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009), CrystalExplorer17 (Turner et al., 2017) and VESTA (Momma & Izumi, 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

catena-Poly[[[bis[2-(trimethylazaniumyl)acetato-κO]sodium]-di-µ-aqua-[diaquasodium]-di-µ-aqua] diiodide] top

Crystal data top

[Na₂(C₅H₁₁NO₂)₂(H₂O)₆]I₂	Z = 2
M_r = 642.17	F(000) = 632
Triclinic, P1	D_x = 1.792 Mg m⁻³
a = 5.8131 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6682 (4) Å	Cell parameters from 9947 reflections
c = 26.7168 (15) Å	θ = 3.1–32.6°
α = 90.221 (2)°	µ = 2.72 mm⁻¹
β = 91.168 (2)°	T = 173 K
γ = 91.440 (3)°	Plate, colourless
V = 1190.29 (11) Å³	0.6 × 0.3 × 0.10 mm

Data collection top

Bruker PHOTON-100 CMOS diffractometer	7237 reflections with I > 2σ(I)
Radiation source: sealedtube	R_int = 0.035
φ and ω scans	θ_max = 32.7°, θ_min = 3.1°
Absorption correction: numerical (SADABS; Krause et al., 2015)	h = −8→8
T_min = 0.076, T_max = 0.252	k = −11→11
49693 measured reflections	l = −40→40
8726 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.050	w = 1/[σ²(F_o²) + (0.0152P)² + 0.5637P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max = 0.001
8726 reflections	Δρ_max = 0.79 e Å⁻³
277 parameters	Δρ_min = −0.42 e Å⁻³
0 restraints

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. Hydrogen atoms of water molecules are refined in isotropic approximation with U_iso (H) = 1.5U_iso (O). Methylene hydrogen atoms are refined with riding coordinates and with U_iso (H) = 1.2 U_iso (C); methyl hydrogen atoms are refined as rotating idealized methyl groups and with U_iso (H) = 1.5U_iso (C).

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

	x	y	z	U_iso*/U_eq
I1	0.87928 (2)	0.75005 (2)	0.42881 (2)	0.02174 (3)
I2	0.38268 (2)	0.75565 (2)	0.07695 (2)	0.02165 (3)
Na1	0.77571 (13)	0.84390 (10)	0.24815 (3)	0.02154 (15)
Na2	0.27301 (12)	0.57053 (9)	0.25452 (3)	0.01983 (15)
O1	1.1105 (3)	0.8215 (2)	0.19938 (6)	0.0281 (3)
H1A	1.120 (5)	0.793 (4)	0.1729 (11)	0.042*
H1B	1.209 (5)	0.891 (4)	0.2024 (10)	0.042*
O2	0.9199 (3)	1.1102 (2)	0.28457 (6)	0.0260 (3)
H2A	0.919 (5)	1.185 (4)	0.2648 (10)	0.039*
H2B	1.044 (5)	1.114 (3)	0.2941 (10)	0.039*
O3	0.4860 (2)	1.04739 (18)	0.21635 (6)	0.0224 (3)
H3A	0.546 (4)	1.121 (3)	0.1998 (10)	0.034*
H3B	0.440 (4)	1.092 (3)	0.2396 (10)	0.034*
O4	0.5880 (2)	0.61769 (19)	0.19940 (5)	0.0225 (3)
H4A	0.555 (4)	0.655 (3)	0.1729 (10)	0.034*
H4B	0.640 (4)	0.522 (3)	0.1953 (9)	0.034*
O5	0.4634 (3)	0.79289 (19)	0.30936 (6)	0.0255 (3)
H5A	0.426 (5)	0.889 (4)	0.3152 (10)	0.038*
H5B	0.521 (5)	0.755 (4)	0.3320 (10)	0.038*
O6	−0.0568 (3)	0.6113 (2)	0.30161 (6)	0.0237 (3)
H6A	−0.046 (5)	0.649 (3)	0.3278 (10)	0.036*
H6B	−0.160 (5)	0.542 (3)	0.3013 (10)	0.036*
O7	0.5321 (2)	0.40694 (17)	0.30561 (5)	0.0241 (3)
O8	0.3744 (2)	0.14234 (16)	0.31642 (5)	0.0208 (3)
O9	0.0750 (3)	0.3559 (2)	0.20861 (5)	0.0327 (3)
O10	−0.2503 (2)	0.29400 (18)	0.16613 (5)	0.0260 (3)
N1	0.4939 (3)	0.24831 (19)	0.42389 (5)	0.0161 (3)
N2	−0.0051 (3)	0.25810 (18)	0.07475 (6)	0.0162 (3)
C1	0.5049 (3)	0.2687 (2)	0.32903 (6)	0.0157 (3)
C2	0.6431 (3)	0.2491 (2)	0.37817 (6)	0.0164 (3)
H2C	0.727987	0.138840	0.377039	0.020*
H2D	0.757875	0.346356	0.381182	0.020*
C3	0.3445 (3)	0.0862 (2)	0.42715 (7)	0.0226 (4)
H3C	0.441301	−0.016571	0.427063	0.034*
H3D	0.237339	0.080643	0.398366	0.034*
H3E	0.257447	0.088892	0.458162	0.034*
C4	0.6520 (3)	0.2557 (3)	0.46896 (7)	0.0236 (4)
H4C	0.750297	0.153754	0.469022	0.035*
H4D	0.560676	0.255836	0.499392	0.035*
H4E	0.748196	0.362354	0.467905	0.035*
C5	0.3436 (3)	0.4046 (2)	0.42398 (8)	0.0235 (4)
H5C	0.254092	0.405303	0.454664	0.035*
H5D	0.238739	0.399377	0.394805	0.035*
H5E	0.439974	0.511094	0.422547	0.035*
C6	−0.0360 (3)	0.3125 (2)	0.17028 (7)	0.0205 (4)
C7	0.1150 (3)	0.2796 (2)	0.12491 (7)	0.0187 (3)
H7A	0.227645	0.378078	0.122540	0.022*
H7B	0.203265	0.173111	0.131526	0.022*
C8	−0.1491 (3)	0.4124 (2)	0.06276 (7)	0.0219 (4)
H8A	−0.273710	0.419352	0.086793	0.033*
H8B	−0.214731	0.399708	0.028827	0.033*
H8C	−0.053026	0.519188	0.064825	0.033*
C9	0.1769 (4)	0.2449 (3)	0.03578 (7)	0.0249 (4)
H9A	0.103387	0.229314	0.002686	0.037*
H9B	0.273443	0.144916	0.043190	0.037*
H9C	0.272600	0.352033	0.036096	0.037*
C10	−0.1531 (3)	0.0948 (2)	0.07263 (8)	0.0242 (4)
H10A	−0.271890	0.100911	0.098044	0.036*
H10B	−0.057606	−0.006544	0.079092	0.036*
H10C	−0.226413	0.083386	0.039385	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.02324 (6)	0.01967 (6)	0.02222 (6)	−0.00166 (4)	0.00118 (5)	−0.00155 (4)
I2	0.02442 (6)	0.01912 (6)	0.02132 (6)	−0.00068 (4)	−0.00071 (5)	0.00098 (4)
Na1	0.0185 (4)	0.0206 (4)	0.0256 (4)	0.0002 (3)	0.0017 (3)	0.0009 (3)
Na2	0.0182 (3)	0.0209 (4)	0.0205 (4)	0.0006 (3)	0.0018 (3)	0.0004 (3)
O1	0.0240 (7)	0.0324 (8)	0.0276 (8)	−0.0055 (6)	0.0063 (6)	−0.0052 (6)
O2	0.0176 (7)	0.0291 (8)	0.0311 (8)	−0.0014 (6)	−0.0019 (6)	0.0021 (6)
O3	0.0230 (7)	0.0215 (7)	0.0225 (7)	−0.0015 (5)	0.0021 (6)	0.0002 (5)
O4	0.0249 (7)	0.0227 (7)	0.0201 (7)	0.0042 (5)	0.0013 (6)	0.0001 (5)
O5	0.0321 (8)	0.0183 (7)	0.0262 (8)	0.0041 (6)	0.0009 (6)	−0.0001 (6)
O6	0.0227 (7)	0.0271 (7)	0.0212 (7)	−0.0035 (5)	0.0035 (6)	−0.0035 (6)
O7	0.0266 (7)	0.0209 (6)	0.0244 (7)	−0.0018 (5)	−0.0044 (6)	0.0074 (5)
O8	0.0201 (6)	0.0193 (6)	0.0227 (7)	−0.0027 (5)	−0.0045 (5)	−0.0011 (5)
O9	0.0439 (9)	0.0337 (8)	0.0200 (7)	−0.0037 (7)	−0.0030 (6)	−0.0054 (6)
O10	0.0245 (7)	0.0270 (7)	0.0267 (7)	−0.0002 (6)	0.0083 (6)	0.0000 (6)
N1	0.0171 (7)	0.0152 (7)	0.0159 (7)	−0.0008 (5)	0.0003 (6)	0.0001 (5)
N2	0.0180 (7)	0.0139 (6)	0.0168 (7)	0.0009 (5)	0.0010 (6)	0.0000 (5)
C1	0.0153 (8)	0.0160 (7)	0.0159 (8)	0.0026 (6)	0.0005 (6)	−0.0001 (6)
C2	0.0144 (8)	0.0188 (8)	0.0160 (8)	−0.0011 (6)	0.0010 (6)	0.0018 (6)
C3	0.0251 (10)	0.0193 (8)	0.0234 (9)	−0.0072 (7)	0.0066 (8)	0.0014 (7)
C4	0.0284 (10)	0.0273 (10)	0.0148 (8)	−0.0008 (8)	−0.0036 (7)	−0.0001 (7)
C5	0.0239 (9)	0.0197 (9)	0.0273 (10)	0.0055 (7)	0.0059 (8)	−0.0019 (7)
C6	0.0298 (10)	0.0129 (8)	0.0188 (9)	−0.0009 (7)	0.0022 (7)	0.0007 (6)
C7	0.0185 (8)	0.0204 (8)	0.0171 (8)	−0.0006 (6)	−0.0017 (7)	0.0017 (7)
C8	0.0254 (9)	0.0174 (8)	0.0229 (9)	0.0041 (7)	−0.0029 (7)	0.0025 (7)
C9	0.0288 (10)	0.0249 (9)	0.0215 (9)	0.0040 (8)	0.0076 (8)	−0.0003 (7)
C10	0.0270 (10)	0.0163 (8)	0.0291 (10)	−0.0049 (7)	0.0003 (8)	−0.0035 (7)

Geometric parameters (Å, º) top

Na1—Na2	3.5607 (10)	N1—C3	1.502 (2)
Na1—Na2ⁱ	3.6149 (10)	N1—C4	1.500 (2)
Na1—O1	2.3733 (17)	N1—C5	1.500 (2)
Na1—O2	2.3842 (17)	N2—C7	1.505 (2)
Na1—O3	2.4650 (16)	N2—C8	1.499 (2)
Na1—O4	2.3926 (16)	N2—C9	1.504 (2)
Na1—O5	2.4926 (17)	N2—C10	1.502 (2)
Na1—O6ⁱ	2.4943 (17)	C1—C2	1.535 (2)
Na2—O1ⁱⁱ	2.6120 (18)	C2—H2C	0.9900
Na2—O4	2.3944 (16)	C2—H2D	0.9900
Na2—O5	2.4697 (17)	C3—H3C	0.9800
Na2—O6	2.3412 (16)	C3—H3D	0.9800
Na2—O7	2.3937 (15)	C3—H3E	0.9800
Na2—O9	2.3175 (16)	C4—H4C	0.9800
O1—H1A	0.74 (3)	C4—H4D	0.9800
O1—H1B	0.78 (3)	C4—H4E	0.9800
O2—H2A	0.78 (3)	C5—H5C	0.9800
O2—H2B	0.76 (3)	C5—H5D	0.9800
O3—H3A	0.80 (3)	C5—H5E	0.9800
O3—H3B	0.76 (3)	C6—C7	1.535 (3)
O4—H4A	0.79 (3)	C7—H7A	0.9900
O4—H4B	0.81 (3)	C7—H7B	0.9900
O5—H5A	0.79 (3)	C8—H8A	0.9800
O5—H5B	0.75 (3)	C8—H8B	0.9800
O6—H6A	0.76 (3)	C8—H8C	0.9800
O6—H6B	0.79 (3)	C9—H9A	0.9800
O7—C1	1.242 (2)	C9—H9B	0.9800
O8—C1	1.256 (2)	C9—H9C	0.9800
O9—C6	1.239 (2)	C10—H10A	0.9800
O10—C6	1.253 (2)	C10—H10B	0.9800
N1—C2	1.513 (2)	C10—H10C	0.9800

O1—Na1—O2	90.91 (6)	C4—N1—C3	108.32 (14)
O1—Na1—O3	115.58 (6)	C4—N1—C5	109.26 (14)
O1—Na1—O4	90.36 (6)	C5—N1—C2	110.53 (14)
O1—Na1—O5	164.44 (6)	C5—N1—C3	108.92 (14)
O1—Na1—O6ⁱ	86.19 (6)	C8—N2—C7	111.16 (14)
O2—Na1—O3	79.70 (5)	C8—N2—C9	108.40 (14)
O2—Na1—O4	167.56 (6)	C8—N2—C10	109.53 (14)
O2—Na1—O5	96.09 (6)	C9—N2—C7	107.71 (14)
O2—Na1—O6ⁱ	104.58 (6)	C10—N2—C7	111.46 (14)
O3—Na1—O5	79.44 (5)	C10—N2—C9	108.49 (14)
O3—Na1—O6ⁱ	157.96 (6)	O7—C1—O8	126.22 (17)
O4—Na1—O3	88.60 (5)	O7—C1—C2	117.31 (15)
O4—Na1—O5	85.80 (5)	O8—C1—C2	116.47 (15)
O4—Na1—O6ⁱ	87.85 (6)	N1—C2—C1	113.03 (14)
O5—Na1—O6ⁱ	78.61 (5)	N1—C2—H2C	109.0
O4—Na2—O1ⁱⁱ	79.92 (5)	N1—C2—H2D	109.0
O4—Na2—O5	86.28 (6)	C1—C2—H2C	109.0
O5—Na2—O1ⁱⁱ	88.89 (6)	C1—C2—H2D	109.0
O6—Na2—O1ⁱⁱ	84.20 (5)	H2C—C2—H2D	107.8
O6—Na2—O4	162.69 (6)	N1—C3—H3C	109.5
O6—Na2—O5	86.57 (6)	N1—C3—H3D	109.5
O6—Na2—O7	106.74 (6)	N1—C3—H3E	109.5
O7—Na2—O1ⁱⁱ	160.57 (6)	H3C—C3—H3D	109.5
O7—Na2—O4	86.76 (5)	H3C—C3—H3E	109.5
O7—Na2—O5	76.09 (5)	H3D—C3—H3E	109.5
O9—Na2—O1ⁱⁱ	92.99 (6)	N1—C4—H4C	109.5
O9—Na2—O4	98.37 (6)	N1—C4—H4D	109.5
O9—Na2—O5	175.22 (6)	N1—C4—H4E	109.5
O9—Na2—O6	89.26 (6)	H4C—C4—H4D	109.5
O9—Na2—O7	102.97 (6)	H4C—C4—H4E	109.5
Na1—O1—Na2ⁱ	92.83 (6)	H4D—C4—H4E	109.5
Na1—O1—H1A	129 (2)	N1—C5—H5C	109.5
Na1—O1—H1B	119 (2)	N1—C5—H5D	109.5
Na2ⁱ—O1—H1A	107 (2)	N1—C5—H5E	109.5
Na2ⁱ—O1—H1B	101 (2)	H5C—C5—H5D	109.5
H1A—O1—H1B	103 (3)	H5C—C5—H5E	109.5
Na1—O2—H2A	111 (2)	H5D—C5—H5E	109.5
Na1—O2—H2B	118 (2)	O9—C6—O10	126.50 (18)
H2A—O2—H2B	102 (3)	O9—C6—C7	113.64 (17)
Na1—O3—H3A	110.1 (18)	O10—C6—C7	119.86 (16)
Na1—O3—H3B	105.0 (19)	N2—C7—C6	117.25 (15)
H3A—O3—H3B	108 (3)	N2—C7—H7A	108.0
Na1—O4—Na2	96.12 (6)	N2—C7—H7B	108.0
Na1—O4—H4A	109.2 (19)	C6—C7—H7A	108.0
Na1—O4—H4B	123.9 (18)	C6—C7—H7B	108.0
Na2—O4—H4A	115.4 (19)	H7A—C7—H7B	107.2
Na2—O4—H4B	104.7 (18)	N2—C8—H8A	109.5
H4A—O4—H4B	107 (3)	N2—C8—H8B	109.5
Na1—O5—H5A	101.7 (19)	N2—C8—H8C	109.5
Na1—O5—H5B	106 (2)	H8A—C8—H8B	109.5
Na2—O5—Na1	91.70 (6)	H8A—C8—H8C	109.5
Na2—O5—H5A	129.2 (19)	H8B—C8—H8C	109.5
Na2—O5—H5B	113 (2)	N2—C9—H9A	109.5
H5A—O5—H5B	110 (3)	N2—C9—H9B	109.5
Na1ⁱⁱ—O6—H6A	106 (2)	N2—C9—H9C	109.5
Na1ⁱⁱ—O6—H6B	100.2 (19)	H9A—C9—H9B	109.5
Na2—O6—Na1ⁱⁱ	96.71 (6)	H9A—C9—H9C	109.5
Na2—O6—H6A	120 (2)	H9B—C9—H9C	109.5
Na2—O6—H6B	121.7 (19)	N2—C10—H10A	109.5
H6A—O6—H6B	108 (3)	N2—C10—H10B	109.5
C1—O7—Na2	131.66 (12)	N2—C10—H10C	109.5
C6—O9—Na2	148.99 (14)	H10A—C10—H10B	109.5
C3—N1—C2	112.49 (14)	H10A—C10—H10C	109.5
C4—N1—C2	107.25 (14)	H10B—C10—H10C	109.5

Na2—O7—C1—O8	32.9 (3)	O10—C6—C7—N2	10.9 (2)
Na2—O7—C1—C2	−147.00 (13)	C3—N1—C2—C1	69.35 (18)
Na2—O9—C6—O10	−101.2 (3)	C4—N1—C2—C1	−171.66 (14)
Na2—O9—C6—C7	79.1 (3)	C5—N1—C2—C1	−52.64 (19)
O7—C1—C2—N1	111.67 (18)	C8—N2—C7—C6	56.0 (2)
O8—C1—C2—N1	−68.3 (2)	C9—N2—C7—C6	174.62 (15)
O9—C6—C7—N2	−169.32 (15)	C10—N2—C7—C6	−66.49 (19)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···I2ⁱ	0.74 (3)	3.03 (3)	3.7008 (17)	152 (3)
O1—H1B···O3ⁱ	0.78 (3)	2.01 (3)	2.781 (2)	172 (3)
O2—H2A···O9ⁱⁱⁱ	0.78 (3)	2.19 (3)	2.915 (2)	154 (3)
O2—H2B···O8ⁱⁱⁱ	0.76 (3)	2.00 (3)	2.7641 (19)	175 (3)
O3—H3A···O10ⁱⁱⁱ	0.80 (3)	1.99 (3)	2.772 (2)	169 (3)
O3—H3B···O8^iv	0.76 (3)	2.13 (3)	2.860 (2)	160 (3)
O4—H4A···I2	0.79 (3)	2.85 (3)	3.6300 (14)	172 (2)
O4—H4B···O10ⁱ	0.81 (3)	2.04 (3)	2.823 (2)	165 (2)
O5—H5A···O8^iv	0.79 (3)	1.97 (3)	2.7484 (19)	167 (3)
O6—H6A···I1ⁱⁱ	0.76 (3)	2.85 (3)	3.5864 (17)	165 (3)
O6—H6B···O7ⁱⁱ	0.79 (3)	2.05 (3)	2.829 (2)	168 (3)
C8—H8A···O10	0.98	2.33	2.976 (2)	122
C3—H3D···O8	0.98	2.39	2.999 (2)	120
C10—H10A···O10	0.98	2.34	2.994 (2)	123

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

Funding information

Financial support from the State University of New York for the acquisition and maintenance of the X-ray diffractometer is gratefully acknowledged.

References

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