metal-organic compounds
Betaine (trimethylammonioacetate) binary compound with sodium iodide
aChemistry Department, SUNY Buffalo State, 1300 Elmwood Ave, Buffalo, NY 14222, USA
*Correspondence e-mail: nazareay@buffalostate.edu
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 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
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.
represent a wide class of 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; GroomThe 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).
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.
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.
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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 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 .
details are summarized in Table 3
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Structural data
CCDC reference: 1848958
https://doi.org/10.1107/S2414314618008647/bv4018sup1.cif
contains datablock I. DOI: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
Data collection: APEX3 (Bruker, 2016); cell
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).[Na2(C5H11NO2)2(H2O)6]I2 | Z = 2 |
Mr = 642.17 | F(000) = 632 |
Triclinic, P1 | Dx = 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 |
Bruker PHOTON-100 CMOS diffractometer | 7237 reflections with I > 2σ(I) |
Radiation source: sealedtube | Rint = 0.035 |
φ and ω scans | θmax = 32.7°, θmin = 3.1° |
Absorption correction: numerical (SADABS; Krause et al., 2015) | h = −8→8 |
Tmin = 0.076, Tmax = 0.252 | k = −11→11 |
49693 measured reflections | l = −40→40 |
8726 independent reflections |
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(Fo2) + (0.0152P)2 + 0.5637P] where P = (Fo2 + 2Fc2)/3 |
S = 1.15 | (Δ/σ)max = 0.001 |
8726 reflections | Δρmax = 0.79 e Å−3 |
277 parameters | Δρmin = −0.42 e Å−3 |
0 restraints |
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 Uiso (H) = 1.5Uiso (O). Methylene hydrogen atoms are refined with riding coordinates and with Uiso (H) = 1.2 Uiso (C); methyl hydrogen atoms are refined as rotating idealized methyl groups and with Uiso (H) = 1.5Uiso (C). |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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. |
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···O8iv | 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···O8iv | 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.
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