Crystal structures of binary compounds of meldonium 3-(1,1,1-tri­methyl­hydrazin-1-ium-2-yl)prop­ano­ate with sodium bromide and sodium iodide

Nazarenko, A.Y.

doi:10.1107/S2056989018006977

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 74| Part 6| June 2018| Pages 829-834

https://doi.org/10.1107/S2056989018006977

Open

access

Crystal structures of binary compounds of meldonium 3-(1,1,1-trimethylhydrazin-1-ium-2-yl)propanoate with sodium bromide and 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 M. Zeller, Purdue University, USA (Received 30 April 2018; accepted 7 May 2018; online 22 May 2018)

3-(1,1,1-Trimethylhydrazin-1-ium-2-yl)propanoate (C₆H₁₄N₂O₂, M, more commonly known under its commercial names Meldonium or Mildronate) co-crystalizes with sodium bromide and sodium iodide forming polymeric hydrates poly[[tetra-μ-aqua-diaquabis[3-(1,1,1-trimethylhydrazin-1-ium-2-yl)propanoate]disodium] dibromide tetrahydrate], [Na₂(C₆H₁₄N₂O₂)₂(H₂O)₆]Br₂·4H₂O, and poly[[di-μ-aqua-diaqua[μ-3-(1,1,1-trimethylhydrazin-1-ium-2-yl)propanoate]disodium] diiodide], [Na₂(C₆H₁₄N₂O₂)₂(H₂O)₄]I₂. The coordination numbers of the sodium ions are 6; the coordination polyhedra can be described as distorted octahedra. Metal ions and M zwitterions are assembled into infinite layers via electrostatic interactions and hydrogen-bonded networks. These layers are connected via electrostatic attraction between halogenide ions and positive trimethylhydrazinium groups into a three-dimensional structure.

Keywords: crystal structure; 3-(1,1,1-trimethylydrhazin-1-ium-2-yl)propanoate; meldonium; sodium bromide; sodium iodide.

CCDC references: 1841872; 1841871

1. Chemical context

3-(1,1,1-Trimethylhydrazin-1-ium-2-yl)propanoate (M), more commonly known under its commercial names such as Meldonium or Mildronate, was introduced by Grindeks (Latvia) as an anti-ischemic medication (Liepinsh et al., 2017 ). The synthesis of M was originally described by Giller et al. (1975 ) and was improved in a number of patents and papers (Kalvins & Stonans, 2009 ; Kalvins et al., 2014 ; Silva, 2013 ). Recently M achieved controversial publicity as a doping agent. As a result of its inclusion in the World Anti-Doping Agency List of Prohibited Substances, it attracted the attention of pharmaceutical and forensic chemists (Görgens et al., 2015 ).

Binary compounds of M with various inorganic salts have been described in numerous M-related synthetic procedures (see above); their high stability was a challenge that was necessary to overcome for the preparation of pharmaceutically pure forms of M. The stability of a sodium iodide binary compound was given as an example in Silva (2013). The crystal structures of two such binary compounds, with sodium bromide (I) and with sodium iodide (II), are presented here.

2. Structural commentary

The labelling schemes for structures (I) and (II) are shown in Figs. 1 and 2. Molecules of (I), which crystallize in an acentric space group, have a non-crystallographic inversion centre at 0.6238 (6) 0.744 (5) 0.5001 (2). This symmetry is visible in Fig. 1; it is also demonstrated by overlay of the two chemically equivalent moieties, after inversion of one of them (Fig. 3). Both Na ions have distorted octahedral environments (coordination number 6). The coordination sphere contains an anionic oxygen atom of a monodentate carboxylic group, two pairs of bridging O atoms of water molecules (O5, O8, O9 and O10), and a terminal water molecule (atoms O6 and O7 for Na1 and Na2 respectively). The shortest Na—O separations (Table 1) correspond to the anionic oxygens O1 and O3; the longest are opposite to the bridging atoms O5 and O8 (not shown in Fig. 1, but visible in Fig. 6).

Table 1
Selected bond lengths (Å) for (I)

Na1—O1	2.367 (4)	Na2—O8	2.364 (3)
Na1—O5	2.368 (3)	Na2—O9	2.361 (3)
Na1—O6	2.369 (3)	Na2—O10	2.449 (4)
Na1—O8ⁱ	2.517 (4)	O1—C1	1.241 (5)
Na1—O9	2.442 (4)	O2—C1	1.281 (5)
Na1—O10	2.361 (4)	O3—C7	1.249 (5)
Na2—O3	2.359 (4)	O4—C7	1.282 (5)
Na2—O5ⁱⁱ	2.543 (4)	N1—N2	1.471 (6)
Na2—O7	2.368 (3)	N3—N4	1.466 (6)
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z.

Figure 1
Labelling scheme of the asymmetric unit of compound (I)

with 50% probability displacement ellipsoids.

Figure 2
Labelling scheme of the asymmetric unit of compound (II)

with 50% probability displacement ellipsoids.

Figure 3
Overlay of the two organic fragments in (I)

after inversion. The average deviation is 0.04 Å.

Figure 6
The infinite chain of hydrated sodium ions along the [010] axis in (I)

The coordination polyhedra of the sodium ions in (II) are visibly different (Fig. 4, Table 2). Both have a distorted octahedral geometry and coordination number 6. The coordination polyhedron of Na1 contains an anionic oxygen atom O1 of a monodentate carboxylic group, atoms O3 and O4 of the bidentate carboxylic acid group, and three water molecules O5, O6, and O8. The O8 atom, which forms three bridging contacts to three different sodium ions, shows a much longer separation from Na1 than any of the other coordinated oxygen atoms (Table 2).

Table 2
Selected bond lengths (Å) for (II)

Na1—O1	2.462 (3)	Na2—O7	2.372 (3)
Na1—O3	2.374 (3)	Na2—O8ⁱⁱⁱ	2.569 (4)
Na1—O4	2.552 (3)	Na2—O8	2.510 (3)
Na1—O5	2.351 (3)	O1—C1	1.274 (4)
Na1—O6	2.385 (4)	O2—C1	1.247 (4)
Na1—O8ⁱ	2.857 (4)	O3—C7	1.256 (5)
Na2—O3	2.315 (3)	O4—C7	1.264 (5)
Na2—O4ⁱⁱ	2.431 (3)	N1—N2	1.478 (4)
Na2—O5ⁱⁱ	2.373 (3)	N3—N4	1.476 (4)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+1.

Figure 4
Coordination polyhedra of the sodium ions in (II)

The octahedral environment around Na2 in (II) (Fig. 4, Table 2) is less distorted: it consists of two bridging oxygen atoms O3 and O4 of two distinct carboxylate groups and four water oxygen atoms. The shortest distance is Na2—O3 (involving carboxylate group oxygens); the two longest again belong to the bridging O8 atoms (Table 2).

All zwitterions of M have approximately the same geometry (the two pseudo-inversion-symmetric zwitterions in the structure of (I) are nearly superimposable, Fig. 3). Both monodentate carboxylates in (I) and that in (II) have slightly elongated C—O bonds for the oxygen atom bound to the corresponding Na ion (Tables 1 and 2). These bonds are slightly longer than the corresponding bonds in M monohydrate and dihydrate [1.258 (2) and 1.2618 (9) Å, respectively; CCDC entries CCDC 1822460 and 1822463; Nazarenko, 2018 ). This relatively small change could be interpreted as a shift of of the anionic charge towards the sodium-bound oxygen atom. The carbon–oxygen bond lengths within the bidenate carboxylate groups in (II) are essentially identical within two standard deviations.

All N—N bond distances are around 1.47 Å (Tables 1 and 2) and are within experimental error indistinguishable from the average value [1.468 (2) Å] for known low-temperature single-crystal structures of M (CCDC 1822460–1822463; Nazarenko, 2018), but significantly shorter than the value reported for room temperature (1.49 Å; Kemme et al., 1983 ).

The distribution of the Hirshfeld surface electrostatic potential of the zwitterion (Fig. 5) shows that only a small area around the carboxyl oxygen atoms is negatively charged: the remaining Hirshfeld surface has positive electrostatic potential. This makes this area attractive for anions, with the N—H group of the hydrazine fragment available as a donor of an electrostatically enhanced hydrogen bond. The lone-pair density of the same hydrazine nitrogen atom is not sufficient to overcome the total positive charge of the trimethylhydrazinium fragment and does not act as a hydrogen-bond acceptor.

Figure 5
Hirshfeld surface of the zwitterion with electrostatic potential plotted using CrystalExplorer17 (Turner et al., 2017

). Red – negative, blue – positive.

3. Supramolecular features

In the structure of (I), the coordination polyhedra of the sodium ions are connected by common edges (a pair of bridging water molecules, O5 and O8, and O9 and O10), forming an infinite chain of ions along the [010] vector (Fig. 6). In addition to Na⋯O interactions, this chain is supported by six hydrogen bonds (Table 3): O6—H6B⋯O2, O5—H5A⋯O1, O8—H8B⋯O3, O7—H7B⋯O4, O9—H9A⋯O6 and O10—H10B⋯O7. The first four of them, connecting the anionic oxygen atoms of the carboxylic groups, are electrostatically enhanced.

Table 3
Hydrogen-bond geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O1ⁱ	0.97 (6)	1.79 (6)	2.746 (4)	172 (6)
O5—H5B⋯O11ⁱⁱⁱ	0.82 (6)	2.02 (6)	2.819 (5)	167 (6)
O6—H6A⋯O4^iv	0.80 (3)	2.06 (3)	2.845 (5)	165 (6)
O6—H6B⋯O2ⁱ	0.82 (3)	1.91 (3)	2.732 (4)	175 (6)
O7—H7A⋯O2^v	0.82 (3)	2.05 (3)	2.856 (5)	165 (6)
O7—H7B⋯O4ⁱⁱ	0.80 (3)	1.94 (3)	2.731 (4)	169 (6)
O8—H8A⋯O13ⁱⁱ	0.81 (3)	2.06 (3)	2.815 (5)	155 (5)
O8—H8B⋯O3ⁱⁱ	0.81 (3)	1.95 (3)	2.754 (4)	168 (7)
O9—H9A⋯O6ⁱⁱ	0.93 (6)	1.96 (6)	2.852 (4)	160 (5)
O9—H9B⋯O13	0.79 (6)	2.01 (6)	2.772 (5)	160 (6)
O10—H10A⋯O11^v	0.78 (6)	2.00 (6)	2.771 (5)	167 (6)
O10—H10B⋯O7ⁱ	0.90 (6)	1.99 (6)	2.853 (4)	158 (5)
O11—H11D⋯O12	0.80 (3)	1.94 (3)	2.744 (6)	179 (7)
O11—H11E⋯O2	0.80 (3)	1.92 (3)	2.719 (5)	174 (9)
O13—H13A⋯O14	0.80 (3)	1.95 (3)	2.733 (6)	170 (6)
O13—H13B⋯O4^iv	0.80 (3)	1.94 (3)	2.727 (5)	168 (9)
N1—H1⋯Br1ⁱ	0.83 (5)	2.57 (5)	3.379 (5)	167 (5)
N3—H3⋯Br2^v	0.84 (5)	2.57 (5)	3.394 (5)	169 (5)
O12—H12D⋯Br1ⁱ	0.80 (5)	2.52 (6)	3.316 (4)	172 (6)
O12—H12E⋯Br1	0.80 (5)	2.49 (6)	3.289 (4)	177 (8)
O14—H14A⋯Br2ⁱ	0.87 (7)	2.47 (7)	3.323 (5)	168 (7)
O14—H14B⋯Br2	0.87 (6)	2.41 (6)	3.281 (5)	175 (6)
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z; (iii) $[x-{\script{1\over 2}}, -y+2, z]$ ; (iv) $[x+{\script{1\over 2}}, -y+2, z]$ ; (v) $[x-{\script{1\over 2}}, -y+1, z]$ .

Each bromide ion forms a hydrogen bond with a hydrazine N—H group. In addition, each of them forms two hydrogen bonds with neighboring water molecules (O12 and O14), thus forming two more infinite chains in the [010] direction. Water molecules O11 and O13 form bridges between the cation chain and the `bromide' chains as hydrogen-bond donors; they are also acceptors of four hydrogen bonds from the water molecules O5 and O10, and O8 and O9 respectively. These hydrogen bonds connect chains into a two-dimensional network. Two more enhanced hydrogen bonds (Table 3), O7—H7A⋯O2 and O6—H6A⋯O4, also connect neighboring chains. The resulting network forms a layer in the (001) plane with the bromide ions and trimethylammonium groups forming each side (Fig. 7). These layers are bound together via electrostatic interaction of the corresponding positive and negative ions; no short intralayer contacts are visible.

Figure 7
Packing of (I)

. View along the [010] axis. Sodium ions are green.

In the structure of (II), the coordination polyhedra of the sodium ions are bridged via the bidentate carboxylate group to form an infinite chain along the [001] axis (Fig. 8). The water molecule O5 provides an additional bridge, stabilizing the chain. These chains are interconnected in the (100) plane with the help of weaker (and longer by almost 0.5 Å) Na⋯O8 contacts (Fig. 9). An array of hydrogen bonds (Table 4, Fig. 9) additionally stabilizes the resulting layer. As in compound (I), both iodide ions are connected to zwitterions M via N—H⋯I⁻ hydrogen bonds. In addition, ion I1 is an acceptor of two hydrogen bonds with water molecules (O6—H6A⋯I1 and O7—H7A⋯I1, see Table 4). In absence of neighboring water molecules, two CH groups of the trimethylammonium fragment form close contacts with the ion I2. As in structure (I), the layers are tied together by the electrostatic interaction of the corresponding positive and negative ions; no short intralayer contacts are visible (Fig. 10).

Table 4
Hydrogen-bond geometry (Å, °) for (II)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5B⋯O1ⁱ	0.85 (6)	1.89 (6)	2.741 (4)	175 (6)
O7—H7B⋯O2^iv	0.91	1.73	2.629 (4)	169
O8—H8A⋯O1ⁱⁱ	0.85 (6)	2.05 (6)	2.815 (4)	149 (6)
N1—H1⋯I2	0.82 (6)	2.87 (6)	3.688 (4)	177 (5)
N3—H3⋯I1^v	0.92 (6)	2.76 (6)	3.650 (3)	161 (5)
O5—H5A⋯O7^v	0.86 (6)	2.00 (6)	2.846 (4)	172 (4)
O6—H6A⋯I1	0.89	2.64	3.518 (3)	166
O6—H6B⋯O4^vi	0.89	1.95	2.825 (4)	168
O7—H7A⋯I1ⁱⁱⁱ	0.91	2.78	3.548 (3)	143
O8—H8B⋯O6ⁱⁱⁱ	0.86 (7)	2.13 (7)	2.989 (5)	175 (5)
C3—H3A⋯I1ⁱⁱ	0.99	3.01	3.920 (4)	154
C11—H11B⋯I2^vii	0.98	3.02	3.975 (4)	165
C12—H12C⋯I1^vi	0.98	2.99	3.952 (5)	167
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+1; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vi) -x+1, -y+1, -z+2; (vii) -x+1, -y, -z+2.

Figure 8
The infinite chain of hydrated sodium ions along the [001] axis in (II)

Figure 9
Chains in the structure of (II)

are connected via atom O8 (in green) and a network of hydrogen bonds (dashed lines).

Figure 10
Packing of (II)

. View along the [001] axis. Sodium ions are green.

4. Database survey

Prior to 2018, the only meldonium-related single-crystal structure in the Cambridge Structural Database (Groom et al., 2016 , CSD Version 5.39) had been a crystal structure of the dihydrate form (refcode CABVOQ; Kemme et al., 1983)) measured at room temperature with no experimental positions for hydrogen atoms. Hydrates of M also were also studied using powder X-ray diffraction (Zvirgzdiņš et al., 2011 ; Bērziņš & Actiņš, 2014 ). Meldonium is closely related to betaines, a wide class of zwitterionic compounds with an onium atom that bears no hydrogen atoms and that is not adjacent to the anionic atom. The parent compound of the betaine class, N,N,N-trimethylglycine (TMG), has a very rich crystal chemistry: the CSD (Version 5.39) contains 217 different structures of its compounds. There are several known crystal structures of TMG 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 ). These compounds show features similar to those of their meldonium analogs: infinite chains of hydrated alkali metal cations and layers of trimethylammonium groups. The obvious differences are the absence of N—H⋯X⁻ hydrogen bonds and the much smaller size of the organic domain.

5. Synthesis and crystallization

Preparation and properties of binary compounds of M with sodium halogenides are described in detail in Giller et al. (1975) and Silva (2013). Commercial M dihydrate was received from Grindeks (Latvia) and recrystallized from propanol-2. Equimolar amounts of it were mixed with sodium iodide and sodium bromide in aqueous ethanol; subsequent slow evaporation yielded crystals suitable for single–crystal X-ray experiments. IR spectra (FTIR–ATR, cm⁻¹) are very similar to those of M dihydrate. (I): 3399 (H₂O), 1571, 1483, 1402, 1320; (II): 3350, 3180 (H₂O), 1568, 1480, 1405, 1317, 1088, 816; M dihydrate: 3201 (H₂O), 1577, 1484, 1404, 1320, 1090, 816.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 5.

Table 5
Experimental details

	(I)	(II)
Crystal data
Chemical formula	[Na₂(C₆H₁₄N₂O₂)₂(H₂O)₆]Br₂·4H₂O	[Na₂(C₆H₁₄N₂O₂)₂(H₂O)₄]·I₂
M_r	678.34	664.23
Crystal system, space group	Orthorhombic, Pca2₁	Monoclinic, P2₁/c
Temperature (K)	173	173
a, b, c (Å)	16.5181 (8), 5.5262 (3), 33.2605 (16)	19.7455 (11), 11.4530 (7), 10.9733 (7)
α, β, γ (°)	90, 90, 90	90, 92.382 (2), 90
V (Å³)	3036.1 (3)	2479.4 (3)
Z	4	4
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	2.76	2.61
Crystal size (mm)	0.65 × 0.13 × 0.09	0.3 × 0.2 × 0.07

Data collection
Diffractometer	Bruker PHOTON-100 CMOS	Bruker PHOTON-100 CMOS
Absorption correction	Numerical (SADABS; Krause et al., 2015 )	Multi-scan (TWINABS; Krause et al., 2015)
T_min, T_max	0.217, 0.635	0.301, 0.431
No. of measured, independent and observed [I > 2σ(I)] reflections	117729, 6969, 6121	5475, 5475, 5012
R_int	0.044	0.048
(sin θ/λ)_max (Å⁻¹)	0.650	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.078, 1.03	0.026, 0.057, 1.17
No. of reflections	6969	5475
No. of parameters	380	286
No. of restraints	33	0
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.38	0.70, −0.55
Absolute structure	Refined as an inversion twin	–
Absolute structure parameter	0.250 (10)	–
Computer programs: APEX2 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL2016 (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ) and CrystalExplorer17 (Turner et al., 2017 ).

Structure (I) was was solved and refined in an achiral space group; the large Flack parameter prompted twin refinement as a two-component inversion twin [0.75 (1):0.25 (1)] with twin matrix [ $[\overline{1}]$ 0 0, 0 $[\overline{1}]$ 0, 0 0 $[\overline{1}]$ ]. Reflections in (II) were processed as a two-domain [0.668 (1):0.332 (1) ratio] non-merohedral twin with twin matrix [1.000 0.000 0.000, 0.000 −1.000 0.000, −0.146 0.000 −1.000]; domain 2 is rotated from the first domain by 180.0° about the reciprocal axis 1.000 −0.001 −0.073 or the real axis 1.000 0.000 0.002 (CELL_NOW; Sheldrick, 2008 ).

In the structure of (I) distances O6—H6A, O6—H6B, O7—H7A, O7—H7B, O8—H8A, and O8—H8B; O11—H11D, O11—H11E, O12—H12E, O12—H12D, O13—H13A, and O13—H13B; O14—H14A and O14—H14B were restrained to be equal with an effective standard deviation of 0.02 Å. Distances N1—H1 and N3—H3 were also restrained to be equal with an effective standard deviation of 0.02 Å; U_iso(H) = 1.5U_iso(N).

In the structure of (II), water molecules O6 and O7 were refined as rotating groups (AFIX 7). The positions and isotropic displacement parameters of the hydrazinium hydrogen atoms were refined.

In both structures, methylene hydrogen atoms were refined with riding coordinates and with U_iso(H) = 1.2 U_iso(C); methyl hydrogen atoms were refined as rotating idealized methyl groups and with U_iso(H) = 1.5U_iso(C). Hydrogen atoms of water molecules were refined in an isotropic approximation with U_iso(H) = 1.5U_iso(O).

Supporting information

CCDC references: 1841872; 1841871

Crystal structure: contains datablocks I, II. DOI: https://doi.org/10.1107/S2056989018006977/zl2729sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018006977/zl2729Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989018006977/zl2729IIsup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989018006977/zl2729Isup4.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2056989018006977/zl2729IIsup5.cdx

checkCIF report

Computing details top

For both structures, data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016). Program(s) used to solve structure: SHELXT (Sheldrick, 2015a) for (I); SHELXT2016 (Sheldrick, 2015a) for (II). Program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b) for (I); SHELXL (Sheldrick, 2015b) for (II). Molecular graphics: OLEX2 (Dolomanov et al., 2009) and CrystalExplorer17 (Turner et al., 2017) for (I); OLEX2 (Dolomanov et al., 2009) for (II). For both structures, software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Poly[[tetra-µ-aqua-diaquabis[3-(1,1,1-trimethylhydrazin-1-ium-2-yl)\ propanoate]disodium] dibromide tetrahydrate] (I) top

Crystal data top

[Na₂(C₆H₁₄N₂O₂)₂(H₂O)₆]Br₂·4H₂O	D_x = 1.484 Mg m⁻³
M_r = 678.34	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca2₁	Cell parameters from 9077 reflections
a = 16.5181 (8) Å	θ = 3.1–27.4°
b = 5.5262 (3) Å	µ = 2.76 mm⁻¹
c = 33.2605 (16) Å	T = 173 K
V = 3036.1 (3) Å³	Needle, colourless
Z = 4	0.65 × 0.13 × 0.09 mm
F(000) = 1408

Data collection top

Bruker PHOTON-100 CMOS diffractometer	6121 reflections with I > 2σ(I)
Radiation source: sealedtube	R_int = 0.044
φ and ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: numerical (SADABS; Krause et al., 2015)	h = −21→21
T_min = 0.217, T_max = 0.635	k = −7→7
117729 measured reflections	l = −43→43
6969 independent reflections

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) + (0.0417P)² + 2.0085P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.078	(Δ/σ)_max = 0.001
S = 1.02	Δρ_max = 0.71 e Å⁻³
6969 reflections	Δρ_min = −0.38 e Å⁻³
380 parameters	Absolute structure: Refined as an inversion twin
33 restraints	Absolute structure parameter: 0.250 (10)
Primary atom site location: dual

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. Refined as a 2-component inversion twin

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

	x	y	z	U_iso*/U_eq
Br1	0.92047 (3)	−0.03168 (8)	0.28604 (2)	0.03549 (13)
Br2	0.82608 (3)	0.44931 (9)	0.71406 (2)	0.04007 (14)
Na1	0.67706 (11)	0.9937 (3)	0.48342 (7)	0.0182 (5)
Na2	0.57098 (11)	0.4989 (3)	0.51722 (7)	0.0186 (5)
O1	0.73577 (16)	0.7342 (5)	0.43488 (9)	0.0229 (6)
O2	0.8552 (2)	0.5504 (5)	0.44213 (11)	0.0240 (7)
O3	0.51258 (17)	0.7566 (5)	0.56578 (9)	0.0243 (6)
O4	0.39361 (19)	0.9443 (5)	0.55827 (11)	0.0226 (6)
O5	0.63384 (19)	1.3548 (5)	0.45166 (9)	0.0237 (6)
H5A	0.671 (4)	1.481 (10)	0.444 (2)	0.036*
H5B	0.594 (3)	1.388 (11)	0.4385 (17)	0.036*
O6	0.78937 (18)	1.2455 (5)	0.49791 (10)	0.0249 (6)
H6A	0.825 (2)	1.210 (10)	0.5134 (14)	0.037*
H6B	0.809 (3)	1.330 (9)	0.4802 (14)	0.037*
O7	0.45879 (18)	0.2480 (5)	0.50216 (10)	0.0255 (6)
H7A	0.423 (3)	0.308 (9)	0.4882 (15)	0.038*
H7B	0.435 (3)	0.173 (10)	0.5193 (14)	0.038*
O8	0.61447 (17)	0.1366 (5)	0.54820 (9)	0.0222 (6)
H8A	0.651 (2)	0.124 (10)	0.5642 (13)	0.033*
H8B	0.584 (3)	0.022 (7)	0.550 (2)	0.033*
O9	0.70252 (18)	0.6523 (5)	0.52830 (10)	0.0240 (6)
H9A	0.729 (3)	0.506 (10)	0.5247 (19)	0.036*
H9B	0.717 (3)	0.707 (10)	0.5492 (19)	0.036*
O10	0.54562 (19)	0.8403 (5)	0.47200 (10)	0.0241 (6)
H10A	0.530 (3)	0.776 (10)	0.4526 (18)	0.036*
H10B	0.507 (4)	0.945 (10)	0.480 (2)	0.036*
N1	0.7581 (3)	0.9463 (7)	0.34771 (14)	0.0243 (9)
H1	0.792 (3)	0.949 (10)	0.3293 (16)	0.037*
N2	0.6865 (3)	1.0657 (6)	0.33042 (12)	0.0308 (9)
N3	0.4899 (3)	0.5316 (7)	0.65254 (15)	0.0254 (9)
H3	0.454 (3)	0.544 (10)	0.6701 (16)	0.038*
N4	0.5581 (3)	0.3991 (7)	0.67014 (13)	0.0398 (10)
C1	0.8094 (2)	0.7177 (7)	0.42815 (12)	0.0180 (8)
C2	0.8516 (3)	0.9122 (8)	0.40294 (14)	0.0266 (9)
H2A	0.886964	1.009290	0.420772	0.032*
H2B	0.886701	0.831769	0.382845	0.032*
C3	0.7943 (3)	1.0812 (7)	0.38121 (13)	0.0240 (9)
H3A	0.751492	1.138148	0.399790	0.029*
H3B	0.824043	1.223813	0.370938	0.029*
C4	0.6963 (4)	1.3329 (8)	0.32444 (18)	0.0457 (14)
H4A	0.697253	1.413826	0.350657	0.069*
H4B	0.650888	1.394886	0.308527	0.069*
H4C	0.747182	1.364707	0.310239	0.069*
C5	0.6719 (4)	0.9498 (8)	0.2904 (2)	0.0416 (14)
H5C	0.719071	0.975629	0.273010	0.062*
H5D	0.623950	1.022298	0.277842	0.062*
H5E	0.663080	0.775844	0.293987	0.062*
C6	0.6167 (4)	1.0165 (10)	0.3575 (2)	0.0382 (14)
H6C	0.607611	0.841579	0.359257	0.057*
H6D	0.568050	1.095072	0.346802	0.057*
H6E	0.628344	1.080630	0.384387	0.057*
C7	0.4383 (2)	0.7743 (7)	0.57220 (12)	0.0190 (8)
C8	0.3960 (3)	0.5814 (8)	0.59707 (14)	0.0270 (9)
H8C	0.361903	0.662841	0.617476	0.032*
H8D	0.359465	0.488736	0.579189	0.032*
C9	0.4512 (3)	0.4059 (7)	0.61824 (13)	0.0244 (9)
H9C	0.419698	0.265265	0.628036	0.029*
H9D	0.493099	0.346329	0.599409	0.029*
C10	0.5447 (5)	0.1391 (10)	0.6751 (2)	0.073 (2)
H10C	0.495470	0.112758	0.691030	0.110*
H10D	0.591059	0.067082	0.689066	0.110*
H10E	0.538397	0.063338	0.648684	0.110*
C11	0.5722 (5)	0.5108 (9)	0.7105 (2)	0.052 (2)
H11A	0.584574	0.683111	0.707269	0.078*
H11B	0.617855	0.429848	0.723737	0.078*
H11C	0.523504	0.492499	0.727074	0.078*
C12	0.6308 (5)	0.4501 (13)	0.6429 (3)	0.0527 (18)
H12A	0.621070	0.379778	0.616269	0.079*
H12B	0.679559	0.377958	0.654625	0.079*
H12C	0.638291	0.625353	0.640292	0.079*
O11	1.0017 (2)	0.4552 (7)	0.40834 (13)	0.0284 (8)
H11D	0.999 (4)	0.458 (11)	0.3843 (8)	0.043*
H11E	0.957 (3)	0.488 (11)	0.417 (3)	0.043*
O12	0.9948 (3)	0.4654 (7)	0.32594 (15)	0.0441 (10)
H12D	0.973 (4)	0.586 (9)	0.318 (2)	0.066*
H12E	0.975 (4)	0.348 (9)	0.316 (2)	0.066*
O13	0.7469 (2)	0.9506 (6)	0.59158 (13)	0.0272 (8)
H13A	0.752 (4)	0.933 (11)	0.6152 (8)	0.041*
H13B	0.793 (2)	0.976 (11)	0.585 (3)	0.041*
O14	0.7528 (3)	0.9447 (8)	0.67369 (14)	0.0489 (11)
H14A	0.777 (5)	1.077 (10)	0.681 (3)	0.073*
H14B	0.771 (4)	0.817 (10)	0.686 (2)	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0441 (3)	0.0355 (2)	0.0268 (3)	−0.0014 (2)	0.0046 (2)	−0.0016 (3)
Br2	0.0516 (3)	0.0410 (2)	0.0277 (3)	0.0037 (2)	0.0026 (3)	0.0051 (3)
Na1	0.0180 (10)	0.0155 (7)	0.0211 (14)	0.0004 (5)	0.0014 (8)	0.0006 (6)
Na2	0.0197 (11)	0.0147 (7)	0.0213 (14)	−0.0003 (6)	−0.0004 (8)	0.0001 (5)
O1	0.0191 (14)	0.0220 (14)	0.0276 (15)	−0.0005 (11)	0.0029 (12)	0.0007 (11)
O2	0.0220 (16)	0.0263 (14)	0.0235 (18)	0.0009 (13)	−0.0005 (13)	0.0040 (13)
O3	0.0198 (15)	0.0244 (14)	0.0287 (16)	0.0009 (12)	0.0051 (11)	0.0023 (12)
O4	0.0200 (16)	0.0248 (14)	0.0230 (17)	0.0007 (12)	−0.0010 (13)	0.0050 (13)
O5	0.0232 (15)	0.0182 (13)	0.0297 (16)	0.0008 (12)	−0.0024 (13)	0.0033 (12)
O6	0.0224 (16)	0.0239 (14)	0.0285 (17)	−0.0023 (12)	−0.0057 (12)	0.0067 (12)
O7	0.0233 (16)	0.0245 (15)	0.0288 (16)	−0.0024 (12)	−0.0030 (12)	0.0071 (12)
O8	0.0227 (15)	0.0179 (13)	0.0261 (16)	−0.0018 (11)	−0.0028 (12)	0.0017 (12)
O9	0.0267 (15)	0.0192 (14)	0.0262 (16)	0.0017 (12)	−0.0042 (13)	−0.0026 (12)
O10	0.0273 (16)	0.0183 (14)	0.0267 (16)	0.0013 (12)	−0.0041 (12)	−0.0031 (11)
N1	0.030 (2)	0.0216 (17)	0.021 (2)	0.0059 (16)	−0.0010 (17)	0.0027 (15)
N2	0.046 (2)	0.0195 (17)	0.027 (2)	0.0025 (16)	−0.0092 (17)	0.0028 (15)
N3	0.031 (2)	0.0231 (17)	0.022 (2)	0.0029 (16)	−0.0017 (18)	−0.0007 (15)
N4	0.061 (3)	0.028 (2)	0.031 (2)	0.012 (2)	−0.021 (2)	−0.0027 (17)
C1	0.022 (2)	0.0159 (17)	0.0157 (19)	−0.0030 (14)	−0.0003 (15)	−0.0020 (14)
C2	0.025 (2)	0.027 (2)	0.028 (2)	−0.0044 (18)	−0.0001 (19)	0.0064 (18)
C3	0.029 (2)	0.0203 (19)	0.023 (2)	0.0013 (17)	−0.0015 (17)	0.0030 (17)
C4	0.066 (4)	0.018 (2)	0.053 (3)	0.002 (2)	−0.019 (3)	0.009 (2)
C5	0.066 (4)	0.032 (2)	0.027 (3)	−0.004 (2)	−0.016 (3)	−0.001 (2)
C6	0.026 (3)	0.049 (3)	0.039 (4)	0.004 (2)	−0.004 (3)	−0.002 (2)
C7	0.024 (2)	0.0187 (18)	0.0142 (19)	−0.0032 (15)	−0.0014 (15)	−0.0030 (14)
C8	0.021 (2)	0.030 (2)	0.030 (2)	−0.0014 (18)	0.0002 (18)	0.0111 (19)
C9	0.028 (2)	0.0211 (19)	0.024 (2)	−0.0028 (17)	−0.0043 (18)	0.0001 (16)
C10	0.116 (6)	0.025 (3)	0.078 (5)	0.003 (3)	−0.056 (4)	0.009 (3)
C11	0.089 (5)	0.039 (3)	0.027 (3)	0.004 (2)	−0.029 (3)	−0.001 (2)
C12	0.040 (4)	0.065 (4)	0.053 (5)	0.017 (3)	−0.008 (3)	−0.015 (3)
O11	0.0229 (18)	0.0383 (17)	0.024 (2)	0.0050 (15)	−0.0012 (15)	0.0031 (16)
O12	0.062 (3)	0.036 (2)	0.034 (2)	−0.0029 (19)	−0.015 (2)	−0.0038 (17)
O13	0.0214 (17)	0.0368 (17)	0.023 (2)	−0.0041 (15)	−0.0035 (15)	0.0007 (15)
O14	0.069 (3)	0.044 (2)	0.033 (3)	0.008 (2)	−0.011 (2)	−0.0001 (19)

Geometric parameters (Å, º) top

Na1—O1	2.367 (4)	N4—C12	1.530 (10)
Na1—O5	2.368 (3)	C1—C2	1.531 (6)
Na1—O6	2.369 (3)	C2—H2A	0.9900
Na1—O8ⁱ	2.517 (4)	C2—H2B	0.9900
Na1—O9	2.442 (4)	C2—C3	1.514 (6)
Na1—O10	2.361 (4)	C3—H3A	0.9900
Na2—O3	2.359 (4)	C3—H3B	0.9900
Na2—O5ⁱⁱ	2.543 (4)	C4—H4A	0.9800
Na2—O7	2.368 (3)	C4—H4B	0.9800
Na2—O8	2.364 (3)	C4—H4C	0.9800
Na2—O9	2.361 (3)	C5—H5C	0.9800
Na2—O10	2.449 (4)	C5—H5D	0.9800
O1—C1	1.241 (5)	C5—H5E	0.9800
O2—C1	1.281 (5)	C6—H6C	0.9800
O3—C7	1.249 (5)	C6—H6D	0.9800
O4—C7	1.282 (5)	C6—H6E	0.9800
O5—H5A	0.97 (6)	C7—C8	1.519 (6)
O5—H5B	0.82 (6)	C8—H8C	0.9900
O6—H6A	0.80 (3)	C8—H8D	0.9900
O6—H6B	0.82 (3)	C8—C9	1.506 (6)
O7—H7A	0.82 (3)	C9—H9C	0.9900
O7—H7B	0.80 (3)	C9—H9D	0.9900
O8—H8A	0.81 (3)	C10—H10C	0.9800
O8—H8B	0.81 (3)	C10—H10D	0.9800
O9—H9A	0.93 (6)	C10—H10E	0.9800
O9—H9B	0.79 (6)	C11—H11A	0.9800
O10—H10A	0.78 (6)	C11—H11B	0.9800
O10—H10B	0.90 (6)	C11—H11C	0.9800
N1—H1	0.83 (4)	C12—H12A	0.9800
N1—N2	1.471 (6)	C12—H12B	0.9800
N1—C3	1.468 (6)	C12—H12C	0.9800
N2—C4	1.499 (6)	O11—H11D	0.80 (3)
N2—C5	1.498 (8)	O11—H11E	0.80 (3)
N2—C6	1.489 (8)	O12—H12D	0.80 (3)
N3—H3	0.84 (4)	O12—H12E	0.80 (3)
N3—N4	1.466 (6)	O13—H13A	0.80 (3)
N3—C9	1.481 (6)	O13—H13B	0.80 (3)
N4—C10	1.463 (7)	O14—H14A	0.87 (5)
N4—C11	1.497 (8)	O14—H14B	0.87 (5)

O1—Na1—O5	109.25 (14)	N3—N4—C11	105.8 (4)
O1—Na1—O6	100.00 (12)	N3—N4—C12	105.9 (4)
O1—Na1—O8ⁱ	160.43 (13)	C10—N4—N3	114.7 (4)
O1—Na1—O9	83.01 (11)	C10—N4—C11	109.1 (5)
O5—Na1—O6	80.32 (12)	C10—N4—C12	111.6 (5)
O5—Na1—O8ⁱ	89.64 (11)	C11—N4—C12	109.5 (5)
O5—Na1—O9	167.30 (15)	O1—C1—O2	124.5 (4)
O6—Na1—O8ⁱ	87.89 (13)	O1—C1—C2	119.6 (4)
O6—Na1—O9	101.22 (13)	O2—C1—C2	115.9 (4)
O9—Na1—O8ⁱ	77.87 (13)	C1—C2—H2A	108.7
O10—Na1—O1	92.84 (12)	C1—C2—H2B	108.7
O10—Na1—O5	87.35 (12)	H2A—C2—H2B	107.6
O10—Na1—O6	164.52 (13)	C3—C2—C1	114.2 (4)
O10—Na1—O8ⁱ	82.69 (12)	C3—C2—H2A	108.7
O10—Na1—O9	88.81 (11)	C3—C2—H2B	108.7
O3—Na2—O5ⁱⁱ	160.55 (13)	N1—C3—C2	107.7 (3)
O3—Na2—O7	100.26 (12)	N1—C3—H3A	110.2
O3—Na2—O8	109.70 (14)	N1—C3—H3B	110.2
O3—Na2—O9	93.04 (13)	C2—C3—H3A	110.2
O3—Na2—O10	83.44 (11)	C2—C3—H3B	110.2
O5ⁱⁱ—Na2—H9A	71.3 (14)	H3A—C3—H3B	108.5
O7—Na2—O5ⁱⁱ	87.40 (13)	N2—C4—H4A	109.5
O7—Na2—H9A	143.9 (13)	N2—C4—H4B	109.5
O7—Na2—O10	100.79 (13)	N2—C4—H4C	109.5
O8—Na2—O5ⁱⁱ	89.11 (11)	H4A—C4—H4B	109.5
O8—Na2—O7	80.45 (11)	H4A—C4—H4C	109.5
O8—Na2—O10	166.49 (15)	H4B—C4—H4C	109.5
O9—Na2—O5ⁱⁱ	82.56 (12)	N2—C5—H5C	109.5
O9—Na2—O7	164.42 (13)	N2—C5—H5D	109.5
O9—Na2—O8	87.49 (12)	N2—C5—H5E	109.5
O9—Na2—O10	88.67 (11)	H5C—C5—H5D	109.5
O10—Na2—O5ⁱⁱ	77.55 (12)	H5C—C5—H5E	109.5
C1—O1—Na1	124.7 (2)	H5D—C5—H5E	109.5
C7—O3—Na2	124.5 (3)	N2—C6—H6C	109.5
Na1—O5—Na2ⁱ	90.26 (13)	N2—C6—H6D	109.5
Na1—O5—H5A	123 (3)	N2—C6—H6E	109.5
Na1—O5—H5B	132 (4)	H6C—C6—H6D	109.5
Na2ⁱ—O5—H5A	106 (4)	H6C—C6—H6E	109.5
Na2ⁱ—O5—H5B	93 (4)	H6D—C6—H6E	109.5
H5A—O5—H5B	102 (5)	O3—C7—O4	124.2 (4)
Na1—O6—H6A	124 (4)	O3—C7—C8	119.3 (4)
Na1—O6—H6B	120 (4)	O4—C7—C8	116.5 (4)
H6A—O6—H6B	108 (6)	C7—C8—H8C	108.4
Na2—O7—H7A	117 (4)	C7—C8—H8D	108.4
Na2—O7—H7B	122 (4)	H8C—C8—H8D	107.5
H7A—O7—H7B	105 (5)	C9—C8—C7	115.3 (4)
Na1ⁱⁱ—O8—H8A	103 (4)	C9—C8—H8C	108.4
Na1ⁱⁱ—O8—H8B	94 (5)	C9—C8—H8D	108.4
Na2—O8—Na1ⁱⁱ	91.00 (13)	N3—C9—C8	108.6 (4)
Na2—O8—H8A	126 (4)	N3—C9—H9C	110.0
Na2—O8—H8B	120 (4)	N3—C9—H9D	110.0
H8A—O8—H8B	111 (6)	C8—C9—H9C	110.0
Na1—O9—H9A	132 (4)	C8—C9—H9D	110.0
Na1—O9—H9B	107 (4)	H9C—C9—H9D	108.3
Na2—O9—Na1	91.34 (13)	N4—C10—H10C	109.5
Na2—O9—H9A	96 (4)	N4—C10—H10D	109.5
Na2—O9—H9B	123 (4)	N4—C10—H10E	109.5
H9A—O9—H9B	108 (5)	H10C—C10—H10D	109.5
Na1—O10—Na2	91.18 (13)	H10C—C10—H10E	109.5
Na1—O10—H10A	127 (4)	H10D—C10—H10E	109.5
Na1—O10—H10B	112 (4)	N4—C11—H11A	109.5
Na2—O10—H10A	102 (4)	N4—C11—H11B	109.5
Na2—O10—H10B	115 (4)	N4—C11—H11C	109.5
H10A—O10—H10B	108 (6)	H11A—C11—H11B	109.5
N2—N1—H1	104 (5)	H11A—C11—H11C	109.5
C3—N1—H1	106 (5)	H11B—C11—H11C	109.5
C3—N1—N2	113.3 (3)	N4—C12—H12A	109.5
N1—N2—C4	114.0 (4)	N4—C12—H12B	109.5
N1—N2—C5	106.6 (4)	N4—C12—H12C	109.5
N1—N2—C6	107.7 (4)	H12A—C12—H12B	109.5
C5—N2—C4	108.7 (4)	H12A—C12—H12C	109.5
C6—N2—C4	110.1 (4)	H12B—C12—H12C	109.5
C6—N2—C5	109.6 (4)	H11D—O11—H11E	107 (8)
N4—N3—H3	108 (4)	H12D—O12—H12E	111 (9)
N4—N3—C9	113.9 (3)	H13A—O13—H13B	102 (8)
C9—N3—H3	106 (5)	H14A—O14—H14B	113 (8)

Na1—O1—C1—O2	99.2 (4)	N4—N3—C9—C8	−167.1 (4)
Na1—O1—C1—C2	−78.2 (4)	C1—C2—C3—N1	−73.2 (5)
Na2—O3—C7—O4	−99.5 (4)	C3—N1—N2—C4	43.8 (6)
Na2—O3—C7—C8	78.8 (4)	C3—N1—N2—C5	163.8 (4)
O1—C1—C2—C3	−12.3 (5)	C3—N1—N2—C6	−78.6 (5)
O2—C1—C2—C3	170.1 (4)	C7—C8—C9—N3	73.4 (5)
O3—C7—C8—C9	10.5 (6)	C9—N3—N4—C10	−42.9 (7)
O4—C7—C8—C9	−171.1 (4)	C9—N3—N4—C11	−163.1 (5)
N2—N1—C3—C2	165.2 (4)	C9—N3—N4—C12	80.7 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O1ⁱ	0.97 (6)	1.79 (6)	2.746 (4)	172 (6)
O5—H5B···O11ⁱⁱⁱ	0.82 (6)	2.02 (6)	2.819 (5)	167 (6)
O6—H6A···O4^iv	0.80 (3)	2.06 (3)	2.845 (5)	165 (6)
O6—H6B···O2ⁱ	0.82 (3)	1.91 (3)	2.732 (4)	175 (6)
O7—H7A···O2^v	0.82 (3)	2.05 (3)	2.856 (5)	165 (6)
O7—H7B···O4ⁱⁱ	0.80 (3)	1.94 (3)	2.731 (4)	169 (6)
O8—H8A···O13ⁱⁱ	0.81 (3)	2.06 (3)	2.815 (5)	155 (5)
O8—H8B···O3ⁱⁱ	0.81 (3)	1.95 (3)	2.754 (4)	168 (7)
O9—H9A···O6ⁱⁱ	0.93 (6)	1.96 (6)	2.852 (4)	160 (5)
O9—H9B···O13	0.79 (6)	2.01 (6)	2.772 (5)	160 (6)
O10—H10A···O11^v	0.78 (6)	2.00 (6)	2.771 (5)	167 (6)
O10—H10B···O7ⁱ	0.90 (6)	1.99 (6)	2.853 (4)	158 (5)
O11—H11D···O12	0.80 (3)	1.94 (3)	2.744 (6)	179 (7)
O11—H11E···O2	0.80 (3)	1.92 (3)	2.719 (5)	174 (9)
O13—H13A···O14	0.80 (3)	1.95 (3)	2.733 (6)	170 (6)
O13—H13B···O4^iv	0.80 (3)	1.94 (3)	2.727 (5)	168 (9)
N1—H1···Br1ⁱ	0.83 (5)	2.57 (5)	3.379 (5)	167 (5)
N3—H3···Br2^v	0.84 (5)	2.57 (5)	3.394 (5)	169 (5)
O12—H12D···Br1ⁱ	0.80 (5)	2.52 (6)	3.316 (4)	172 (6)
O12—H12E···Br1	0.80 (5)	2.49 (6)	3.289 (4)	177 (8)
O14—H14A···Br2ⁱ	0.87 (7)	2.47 (7)	3.323 (5)	168 (7)
O14—H14B···Br2	0.87 (6)	2.41 (6)	3.281 (5)	175 (6)

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

Poly[[di-µ-aqua-diaquabis[µ-3-(1,1,1-trimethylhydrazin-1-ium-2-yl)\ propanoate]disodium] diiodide] (II) top

Crystal data top

[Na₂(C₆H₁₄N₂O₂)₂(H₂O)₄]·I₂	F(000) = 1312
M_r = 664.23	D_x = 1.779 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.7455 (11) Å	Cell parameters from 9932 reflections
b = 11.4530 (7) Å	θ = 3.1–27.9°
c = 10.9733 (7) Å	µ = 2.61 mm⁻¹
β = 92.382 (2)°	T = 173 K
V = 2479.4 (3) Å³	Plate, colourless
Z = 4	0.3 × 0.2 × 0.07 mm

Data collection top

Bruker PHOTON-100 CMOS diffractometer	5012 reflections with I > 2σ(I)
Radiation source: sealedtube	R_int = 0.048
φ and ω scans	θ_max = 27.1°, θ_min = 2.7°
Absorption correction: multi-scan (TWINABS; Krause et al., 2015)	h = −25→25
T_min = 0.301, T_max = 0.431	k = 0→14
5475 measured reflections	l = 0→14
5475 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.057	w = 1/[σ²(F_o²) + (0.0177P)² + 4.3911P] where P = (F_o² + 2F_c²)/3
S = 1.17	(Δ/σ)_max = 0.001
5475 reflections	Δρ_max = 0.70 e Å⁻³
286 parameters	Δρ_min = −0.55 e Å⁻³

Special details top

Refinement. Refined as a 2-component twin.

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

	x	y	z	U_iso*/U_eq
I1	0.25574 (2)	0.48014 (2)	0.74401 (2)	0.01967 (6)
I2	0.02717 (2)	0.01593 (2)	0.75216 (2)	0.02095 (7)
Na1	0.45889 (8)	0.30771 (15)	0.87401 (15)	0.0228 (4)
Na2	0.54574 (8)	0.37173 (13)	0.56036 (14)	0.0177 (3)
H5A	0.412 (3)	0.150 (5)	1.034 (5)	0.048 (18)*
O1	0.38099 (12)	0.1816 (2)	0.7525 (3)	0.0205 (5)
O2	0.29207 (14)	0.0789 (3)	0.8118 (2)	0.0219 (6)
O3	0.55979 (13)	0.3377 (3)	0.7678 (3)	0.0252 (6)
O4	0.57944 (14)	0.3107 (3)	0.9672 (2)	0.0193 (6)
O5	0.43527 (15)	0.2101 (3)	1.0559 (3)	0.0212 (6)
H5B	0.418 (3)	0.246 (5)	1.113 (5)	0.038 (15)*
O6	0.42378 (16)	0.5067 (3)	0.8601 (3)	0.0273 (7)
H6A	0.382266	0.512961	0.824831	0.041*
H6B	0.428059	0.568362	0.908724	0.041*
O7	0.63392 (14)	0.4980 (2)	0.5020 (3)	0.0225 (6)
H7A	0.659951	0.465242	0.444491	0.034*
H7B	0.662743	0.517998	0.565473	0.034*
O8	0.49586 (16)	0.4327 (3)	0.3560 (3)	0.0225 (6)
H8A	0.459 (3)	0.425 (5)	0.314 (6)	0.049 (17)*
H8B	0.517 (3)	0.453 (5)	0.292 (7)	0.06 (2)*
N1	0.16954 (18)	0.1758 (3)	0.6228 (3)	0.0167 (7)
H1	0.137 (3)	0.143 (5)	0.651 (5)	0.044 (17)*
N2	0.13426 (15)	0.2379 (3)	0.5206 (3)	0.0142 (7)
N3	0.78736 (16)	0.2584 (3)	0.9016 (3)	0.0180 (7)
H3	0.783 (3)	0.195 (5)	0.850 (5)	0.049 (17)*
N4	0.83846 (16)	0.2233 (3)	0.9966 (3)	0.0183 (8)
C1	0.32344 (17)	0.1332 (3)	0.7334 (4)	0.0155 (7)
C2	0.29341 (19)	0.1380 (4)	0.6039 (4)	0.0202 (8)
H2A	0.323168	0.092864	0.550794	0.024*
H2B	0.294100	0.220190	0.576042	0.024*
C3	0.22141 (19)	0.0918 (3)	0.5852 (4)	0.0186 (8)
H3A	0.213016	0.072622	0.497921	0.022*
H3B	0.216958	0.018875	0.632569	0.022*
C4	0.0888 (2)	0.3230 (4)	0.5808 (4)	0.0227 (9)
H4A	0.055992	0.280383	0.628483	0.034*
H4B	0.064620	0.370023	0.518335	0.034*
H4C	0.116052	0.374288	0.634871	0.034*
C5	0.0924 (2)	0.1603 (4)	0.4372 (4)	0.0204 (9)
H5C	0.122247	0.106328	0.395452	0.031*
H5D	0.067248	0.208076	0.376722	0.031*
H5E	0.060508	0.115656	0.484926	0.031*
C6	0.1844 (2)	0.3039 (4)	0.4481 (4)	0.0197 (8)
H6C	0.212631	0.352880	0.503036	0.029*
H6D	0.160127	0.353351	0.387941	0.029*
H6E	0.213223	0.248583	0.406033	0.029*
C7	0.59886 (19)	0.3209 (3)	0.8594 (3)	0.0149 (8)
C8	0.67425 (19)	0.3096 (3)	0.8349 (3)	0.0176 (8)
H8C	0.680210	0.244686	0.776752	0.021*
H8D	0.689360	0.382222	0.795342	0.021*
C9	0.71953 (19)	0.2876 (3)	0.9479 (4)	0.0185 (8)
H9A	0.722229	0.358018	1.000169	0.022*
H9B	0.701879	0.221932	0.996013	0.022*
C10	0.8943 (2)	0.1664 (4)	0.9296 (4)	0.0270 (10)
H10A	0.876446	0.097529	0.885963	0.040*
H10B	0.930579	0.142601	0.987910	0.040*
H10C	0.912211	0.221802	0.871014	0.040*
C11	0.8123 (2)	0.1393 (4)	1.0886 (4)	0.0309 (10)
H11A	0.779170	0.178956	1.138310	0.046*
H11B	0.850060	0.111068	1.141379	0.046*
H11C	0.790487	0.073026	1.046252	0.046*
C12	0.8657 (2)	0.3300 (4)	1.0583 (5)	0.0290 (10)
H12A	0.883202	0.383425	0.997423	0.044*
H12B	0.902343	0.308279	1.116894	0.044*
H12C	0.829389	0.368612	1.101424	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.02077 (12)	0.02229 (12)	0.01602 (12)	−0.00185 (10)	0.00150 (12)	0.00076 (10)
I2	0.01730 (12)	0.02514 (12)	0.02035 (14)	−0.00498 (9)	−0.00011 (13)	0.00198 (10)
Na1	0.0199 (8)	0.0258 (9)	0.0226 (8)	−0.0008 (7)	−0.0001 (7)	0.0014 (7)
Na2	0.0173 (7)	0.0207 (8)	0.0151 (7)	−0.0017 (6)	0.0004 (6)	−0.0007 (6)
O1	0.0172 (13)	0.0235 (13)	0.0206 (13)	−0.0024 (10)	−0.0028 (11)	0.0040 (11)
O2	0.0199 (14)	0.0282 (16)	0.0178 (14)	−0.0012 (12)	0.0016 (11)	0.0040 (12)
O3	0.0190 (14)	0.0382 (16)	0.0181 (15)	0.0030 (11)	−0.0012 (12)	0.0042 (13)
O4	0.0182 (14)	0.0237 (15)	0.0160 (14)	−0.0010 (12)	0.0017 (11)	0.0015 (11)
O5	0.0166 (15)	0.0250 (16)	0.0223 (16)	−0.0002 (12)	0.0036 (12)	−0.0047 (13)
O6	0.0216 (16)	0.0324 (18)	0.0276 (16)	0.0020 (13)	−0.0013 (12)	−0.0066 (13)
O7	0.0194 (15)	0.0321 (17)	0.0162 (13)	−0.0044 (13)	0.0040 (11)	−0.0036 (12)
O8	0.0207 (17)	0.0298 (17)	0.0168 (15)	−0.0035 (13)	−0.0013 (13)	0.0015 (12)
N1	0.0169 (18)	0.0223 (18)	0.0107 (15)	−0.0012 (15)	−0.0017 (13)	0.0015 (13)
N2	0.0138 (14)	0.0175 (18)	0.0112 (17)	0.0014 (14)	−0.0011 (13)	−0.0009 (11)
N3	0.0145 (17)	0.0221 (18)	0.0173 (17)	0.0033 (14)	−0.0005 (13)	−0.0014 (13)
N4	0.0143 (15)	0.020 (2)	0.0202 (18)	0.0029 (12)	−0.0018 (14)	−0.0014 (14)
C1	0.0142 (17)	0.0135 (16)	0.0188 (18)	0.0056 (13)	0.0015 (15)	−0.0011 (14)
C2	0.014 (2)	0.027 (2)	0.019 (2)	−0.0001 (17)	0.0005 (16)	0.0008 (17)
C3	0.0186 (19)	0.018 (2)	0.0184 (19)	−0.0011 (16)	−0.0020 (16)	0.0012 (15)
C4	0.024 (2)	0.021 (2)	0.022 (2)	0.0074 (18)	0.0002 (18)	−0.0036 (17)
C5	0.021 (2)	0.024 (2)	0.0159 (19)	−0.0038 (18)	−0.0056 (16)	−0.0041 (16)
C6	0.018 (2)	0.022 (2)	0.019 (2)	−0.0033 (16)	−0.0001 (16)	0.0030 (16)
C7	0.0135 (19)	0.0137 (19)	0.0176 (18)	−0.0011 (15)	0.0006 (15)	0.0009 (14)
C8	0.019 (2)	0.0152 (19)	0.0182 (18)	0.0030 (15)	0.0011 (15)	0.0014 (14)
C9	0.0172 (19)	0.019 (2)	0.0194 (19)	0.0007 (15)	0.0032 (15)	0.0012 (15)
C10	0.015 (2)	0.034 (3)	0.032 (2)	0.0107 (19)	0.0003 (18)	−0.006 (2)
C11	0.027 (2)	0.042 (3)	0.023 (2)	0.006 (2)	−0.0025 (19)	0.013 (2)
C12	0.022 (2)	0.028 (3)	0.037 (3)	0.0025 (19)	−0.005 (2)	−0.011 (2)

Geometric parameters (Å, º) top

Na1—Na2ⁱ	3.325 (2)	N3—N4	1.476 (4)
Na1—Na2	3.977 (2)	N3—C9	1.490 (5)
Na1—O1	2.462 (3)	N4—C10	1.499 (5)
Na1—O3	2.374 (3)	N4—C11	1.502 (5)
Na1—O4	2.552 (3)	N4—C12	1.487 (6)
Na1—O5	2.351 (3)	C1—C2	1.518 (5)
Na1—O6	2.385 (4)	C2—H2A	0.9900
Na1—O8ⁱ	2.857 (4)	C2—H2B	0.9900
Na1—C7	2.779 (4)	C2—C3	1.522 (5)
Na2—Na2ⁱⁱ	3.668 (3)	C3—H3A	0.9900
Na2—O3	2.315 (3)	C3—H3B	0.9900
Na2—O4ⁱⁱⁱ	2.431 (3)	C4—H4A	0.9800
Na2—O5ⁱⁱⁱ	2.373 (3)	C4—H4B	0.9800
Na2—O7	2.372 (3)	C4—H4C	0.9800
Na2—O8ⁱⁱ	2.569 (4)	C5—H5C	0.9800
Na2—O8	2.510 (3)	C5—H5D	0.9800
O1—C1	1.274 (4)	C5—H5E	0.9800
O2—C1	1.247 (4)	C6—H6C	0.9800
O3—C7	1.256 (5)	C6—H6D	0.9800
O4—C7	1.264 (5)	C6—H6E	0.9800
O5—H5A	0.86 (6)	C7—C8	1.529 (5)
O5—H5B	0.84 (6)	C8—H8C	0.9900
O6—H6A	0.8946	C8—H8D	0.9900
O6—H6B	0.8873	C8—C9	1.520 (5)
O7—H7A	0.9110	C9—H9A	0.9900
O7—H7B	0.9103	C9—H9B	0.9900
O8—H8A	0.85 (6)	C10—H10A	0.9800
O8—H8B	0.86 (7)	C10—H10B	0.9800
N1—H1	0.83 (6)	C10—H10C	0.9800
N1—N2	1.478 (4)	C11—H11A	0.9800
N1—C3	1.476 (5)	C11—H11B	0.9800
N2—C4	1.496 (5)	C11—H11C	0.9800
N2—C5	1.499 (5)	C12—H12A	0.9800
N2—C6	1.500 (5)	C12—H12B	0.9800
N3—H3	0.92 (6)	C12—H12C	0.9800

O1—Na1—O4	140.94 (12)	N3—N4—C10	105.5 (3)
O1—Na1—O8ⁱ	63.43 (9)	N3—N4—C11	113.9 (3)
O1—Na1—C7	126.95 (12)	N3—N4—C12	108.8 (3)
O3—Na1—O1	109.70 (11)	C10—N4—C11	109.4 (3)
O3—Na1—O4	53.63 (9)	C12—N4—C10	108.8 (3)
O3—Na1—O6	94.48 (12)	C12—N4—C11	110.3 (4)
O3—Na1—O8ⁱ	83.30 (11)	O1—C1—C2	116.7 (3)
O3—Na1—C7	26.77 (10)	O2—C1—O1	124.6 (4)
O4—Na1—O8ⁱ	78.70 (10)	O2—C1—C2	118.6 (3)
O4—Na1—C7	27.00 (10)	C1—C2—H2A	108.3
O5—Na1—O1	92.25 (11)	C1—C2—H2B	108.3
O5—Na1—O3	133.27 (12)	C1—C2—C3	116.1 (3)
O5—Na1—O4	83.16 (11)	H2A—C2—H2B	107.4
O5—Na1—O6	116.18 (13)	C3—C2—H2A	108.3
O5—Na1—O8ⁱ	70.18 (11)	C3—C2—H2B	108.3
O5—Na1—C7	107.91 (12)	N1—C3—C2	113.0 (3)
O6—Na1—O1	110.65 (11)	N1—C3—H3A	109.0
O6—Na1—O4	106.06 (12)	N1—C3—H3B	109.0
O6—Na1—O8ⁱ	172.17 (12)	C2—C3—H3A	109.0
O6—Na1—C7	103.39 (12)	C2—C3—H3B	109.0
C7—Na1—O8ⁱ	77.92 (11)	H3A—C3—H3B	107.8
O3—Na2—O4ⁱⁱⁱ	104.18 (11)	N2—C4—H4A	109.5
O3—Na2—O5ⁱⁱⁱ	91.51 (11)	N2—C4—H4B	109.5
O3—Na2—O7	108.00 (12)	N2—C4—H4C	109.5
O3—Na2—O8	162.13 (12)	H4A—C4—H4B	109.5
O3—Na2—O8ⁱⁱ	79.78 (11)	H4A—C4—H4C	109.5
O4ⁱⁱⁱ—Na2—O8ⁱⁱ	175.55 (12)	H4B—C4—H4C	109.5
O4ⁱⁱⁱ—Na2—O8	88.14 (11)	N2—C5—H5C	109.5
O5ⁱⁱⁱ—Na2—O4ⁱⁱⁱ	85.36 (11)	N2—C5—H5D	109.5
O5ⁱⁱⁱ—Na2—O8ⁱⁱ	92.56 (12)	N2—C5—H5E	109.5
O5ⁱⁱⁱ—Na2—O8	76.41 (11)	H5C—C5—H5D	109.5
O7—Na2—O4ⁱⁱⁱ	101.17 (11)	H5C—C5—H5E	109.5
O7—Na2—O5ⁱⁱⁱ	156.89 (13)	H5D—C5—H5E	109.5
O7—Na2—O8	81.63 (11)	N2—C6—H6C	109.5
O7—Na2—O8ⁱⁱ	79.28 (11)	N2—C6—H6D	109.5
O8—Na2—O8ⁱⁱ	87.55 (11)	N2—C6—H6E	109.5
C1—O1—Na1	151.3 (3)	H6C—C6—H6D	109.5
C7—O3—Na1	94.9 (2)	H6C—C6—H6E	109.5
C7—O3—Na2	149.0 (2)	H6D—C6—H6E	109.5
Na2ⁱ—O4—Na1	83.67 (10)	O3—C7—Na1	58.34 (19)
C7—O4—Na1	86.6 (2)	O3—C7—O4	124.2 (3)
C7—O4—Na2ⁱ	124.9 (3)	O3—C7—C8	116.2 (3)
Na1—O5—Na2ⁱ	89.48 (11)	O4—C7—Na1	66.4 (2)
Na1—O5—H5A	105 (4)	O4—C7—C8	119.5 (3)
Na1—O5—H5B	120 (4)	C8—C7—Na1	169.5 (3)
Na2ⁱ—O5—H5A	99 (4)	C7—C8—H8C	108.6
Na2ⁱ—O5—H5B	126 (4)	C7—C8—H8D	108.6
H5A—O5—H5B	112 (5)	H8C—C8—H8D	107.6
Na1—O6—H6A	111.3	C9—C8—C7	114.5 (3)
Na1—O6—H6B	134.6	C9—C8—H8C	108.6
H6A—O6—H6B	105.0	C9—C8—H8D	108.6
Na2—O7—H7A	112.2	N3—C9—C8	105.4 (3)
Na2—O7—H7B	112.9	N3—C9—H9A	110.7
H7A—O7—H7B	106.3	N3—C9—H9B	110.7
Na1ⁱⁱⁱ—O8—H8A	74 (4)	C8—C9—H9A	110.7
Na1ⁱⁱⁱ—O8—H8B	117 (4)	C8—C9—H9B	110.7
Na2—O8—Na1ⁱⁱⁱ	76.24 (10)	H9A—C9—H9B	108.8
Na2ⁱⁱ—O8—Na1ⁱⁱⁱ	136.82 (13)	N4—C10—H10A	109.5
Na2—O8—Na2ⁱⁱ	92.45 (11)	N4—C10—H10B	109.5
Na2—O8—H8A	139 (4)	N4—C10—H10C	109.5
Na2ⁱⁱ—O8—H8A	90 (4)	H10A—C10—H10B	109.5
Na2—O8—H8B	129 (4)	H10A—C10—H10C	109.5
Na2ⁱⁱ—O8—H8B	103 (4)	H10B—C10—H10C	109.5
H8A—O8—H8B	90 (5)	N4—C11—H11A	109.5
N2—N1—H1	99 (4)	N4—C11—H11B	109.5
C3—N1—H1	112 (4)	N4—C11—H11C	109.5
C3—N1—N2	114.3 (3)	H11A—C11—H11B	109.5
N1—N2—C4	104.6 (3)	H11A—C11—H11C	109.5
N1—N2—C5	114.1 (3)	H11B—C11—H11C	109.5
N1—N2—C6	110.1 (3)	N4—C12—H12A	109.5
C4—N2—C5	109.3 (3)	N4—C12—H12B	109.5
C4—N2—C6	109.1 (3)	N4—C12—H12C	109.5
C5—N2—C6	109.5 (3)	H12A—C12—H12B	109.5
N4—N3—H3	105 (4)	H12A—C12—H12C	109.5
N4—N3—C9	114.7 (3)	H12B—C12—H12C	109.5
C9—N3—H3	109 (4)

Na1—O1—C1—O2	−48.2 (7)	O2—C1—C2—C3	9.4 (5)
Na1—O1—C1—C2	134.9 (4)	O3—C7—C8—C9	−179.1 (3)
Na1—O3—C7—O4	−8.8 (4)	O4—C7—C8—C9	−0.5 (5)
Na1—O3—C7—C8	169.7 (3)	N2—N1—C3—C2	102.5 (4)
Na1—O4—C7—O3	8.2 (4)	N4—N3—C9—C8	−174.9 (3)
Na1—O4—C7—C8	−170.3 (3)	C1—C2—C3—N1	78.7 (4)
Na1—C7—C8—C9	−122.6 (14)	C3—N1—N2—C4	−175.9 (3)
Na2—O3—C7—Na1	−175.0 (6)	C3—N1—N2—C5	64.8 (4)
Na2—O3—C7—O4	176.2 (3)	C3—N1—N2—C6	−58.8 (4)
Na2—O3—C7—C8	−5.3 (7)	C7—C8—C9—N3	170.1 (3)
Na2ⁱ—O4—C7—Na1	79.9 (2)	C9—N3—N4—C10	164.3 (3)
Na2ⁱ—O4—C7—O3	88.0 (5)	C9—N3—N4—C11	44.3 (4)
Na2ⁱ—O4—C7—C8	−90.4 (4)	C9—N3—N4—C12	−79.2 (4)
O1—C1—C2—C3	−173.5 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O1ⁱ	0.85 (6)	1.89 (6)	2.741 (4)	175 (6)
O7—H7B···O2^iv	0.91	1.73	2.629 (4)	169
O8—H8A···O1ⁱⁱⁱ	0.85 (6)	2.05 (6)	2.815 (4)	149 (6)
N1—H1···I2	0.82 (6)	2.87 (6)	3.688 (4)	177 (5)
N3—H3···I1^v	0.92 (6)	2.76 (6)	3.650 (3)	161 (5)
O5—H5A···O7^v	0.86 (6)	2.00 (6)	2.846 (4)	172 (4)
O6—H6A···I1	0.89	2.64	3.518 (3)	166
O6—H6B···O4^vi	0.89	1.95	2.825 (4)	168
O7—H7A···I1ⁱⁱ	0.91	2.78	3.548 (3)	143
O8—H8B···O6ⁱⁱ	0.86 (7)	2.13 (7)	2.989 (5)	175 (5)
C3—H3A···I1ⁱⁱⁱ	0.99	3.01	3.920 (4)	154
C11—H11B···I2^vii	0.98	3.02	3.975 (4)	165
C12—H12C···I1^vi	0.98	2.99	3.952 (5)	167

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+1/2, z−1/2; (iv) −x+1, y+1/2, −z+3/2; (v) −x+1, y−1/2, −z+3/2; (vi) −x+1, −y+1, −z+2; (vii) −x+1, −y, −z+2.

Funding information

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

References

Andrade, L. C. R., Costa, M. M. R., Paixao, J., Agostinho Moreira, J., Almeida, A., Chaves, M. R. & Klopperpieper, A. (1999). Z. Kristallogr. New Cryst. Struct. 214, 83–84. Google Scholar
Andrade, L. C. R., Costa, M. M. R., Pinto, F., Paixao, J. A., Almeida, A., Chaves, M. R. & Klopperpieper, A. (2000). Z. Kristallogr. New Cryst. Struct. 215, 537–538. Google Scholar
Andrade, L. C. R., Costa, M. M. R., Pinto, F., Rodrigues, V. H., Paixao, J. A., Almeida, A., Chaves, M. R. & Klopperpieper, A. (2001). Z. Kristallogr. New Cryst. Struct. 216, 227–228. Google Scholar
Bērziņš, A. & Actiņš, A. (2014). CrystEngComm, 16, 3926–3934. Google Scholar
Bruker (2016). APEX3 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Giller, S. A., Eremeev, A. V., Kalvin'sh, I. Y., Liepin'sh, É. É., & Semenikhina, V. G. (1975). Chem. Heterocycl. Compd. 11, 1378–1382. CrossRef Google Scholar
Görgens, C., Guddat, S., Dib, J., Geyer, H., Schänzer, W. & Thevis, M. (2015). Drug Test. Anal. 7, 973–979. Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kalvins, I., Liepins, E., Loza, E., Dambrova, M., Stonans, L., Lola, D., Kuka, J., Pugovics, O., Vilskersts, R. & Grinberga, S. (2014). US Patent, US 20140088125 A1. Google Scholar
Kalvins, I. & Stonans, I. (2009). WO Patent, WO/2009/071586. Google Scholar
Kemme, A., Bleidelis, J., Kalvinsh, I. & Eremeev, A. (1983). Latv. PSR Zinat. Akad. Vestis, 2, 215–218. Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Liepinsh, E., Makarova, E., Sevostjanovs, E., Hartmane, D., Cirule, H., Zharkova-Malkova, O., Grinberga, S. & Dambrova, M. (2017). Basic & Clinical Pharmacology & Toxicology 120, 450-456. CrossRef Google Scholar
Nazarenko, A. Y. (2018). Private communication (refcodes CCDC 1822460–1822463. CCDC, Cambridge, England. Google Scholar
Rodrigues, V. H., Costa, M. M. R., Klopperpieper, A., Chaves, M. R., Almeida, A. & Agostinho Moreira, J. (2005). Z. Kristallogr. New Cryst. Struct. 220, 363–364. Google Scholar
Sheldrick, G. M. (2008). CELL_NOW. Version 2008/4. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Silva, J. (2013). Patent CA 2661357 C, 2013. Google Scholar
Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). CrystalExplorer17. University of Western Australia. https://hirshfeldsurface.net Google Scholar
Zvirgzdiņš, A., Veldre, K. & Actiņš, A. (2011). Latvian J. Chem. 50, 64–72. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 74| Part 6| June 2018| Pages 829-834

https://doi.org/10.1107/S2056989018006977

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structures of binary compounds of meldonium 3-(1,1,1-tri­methyl­hydrazin-1-ium-2-yl)prop­ano­ate with sodium bromide and sodium iodide

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Funding information

References

research communications

Crystal structures of binary compounds of meldonium 3-(1,1,1-trimethylhydrazin-1-ium-2-yl)propanoate with sodium bromide and sodium iodide

3. Supramolecular features