Crystal structures and Hirshfeld surface analyses of N,N-di­methyl­acetamide–1-(dimethyl-λ4-aza­nyl­idene)ethan-1-ol tribromide (1/1), N,N-di­methyl­acetamide–1-(dimethyl-λ4-aza­nyl­idene)ethan-1-ol di­bromido­iodate (1/1) and N,N-di­methyl­acetamide–1-(dimethyl-λ4-aza­nyl­idene)ethan-1-ol di­chlorido­iodate (1/1)

Mammadova, G.Z.; Mertsalov, D.F.; Shchevnikov, D.M.; Grigoriev, M.S.; Akkurt, M.; Yıldırım, S. Ö.; Bhattarai, A.

doi:10.1107/S2056989023005509

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ISSN: 2056-9890

Volume 79| Part 8| August 2023| Pages 690-697

https://doi.org/10.1107/S2056989023005509

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Crystal structures and Hirshfeld surface analyses of N,N-dimethylacetamide–1-(dimethyl-λ⁴-azanylidene)ethan-1-ol tribromide (1/1), N,N-dimethylacetamide–1-(dimethyl-λ⁴-azanylidene)ethan-1-ol dibromidoiodate (1/1) and N,N-dimethylacetamide–1-(dimethyl-λ⁴-azanylidene)ethan-1-ol dichloridoiodate (1/1)

Gunay Z. Mammadova,^a Dmitriy F. Mertsalov,^b Dmitriy M. Shchevnikov,^b Mikhail S. Grigoriev,^c Mehmet Akkurt,^d Sema Öztürk Yıldırım ^d,^e and Ajaya Bhattarai ^f ^*

^aOrganic Chemistry Department, Baku State University, Z. Xalilov Str. 23, Az 1148 Baku, Azerbaijan, ^bPeoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation, ^cFrumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky pr. 31, bld. 4, Moscow 119071, Russian Federation, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, ^eDepartment of Physics, Faculty of Science, Eskisehir Technical University, Yunus Emre Campus, 26470 Eskisehir, Türkiye, and ^fDepartment of Chemistry, M.M.A.M.C., Tribhuvan University, Biratnagar, Nepal
^*Correspondence e-mail: ajaya.bhattarai@mmamc.tu.edu.np

Edited by C. Schulzke, Universität Greifswald, Germany (Received 8 May 2023; accepted 22 June 2023; online 4 July 2023)

In the title compounds, N,N-dimethylacetamide–1-(dimethyl-λ⁴-azanylidene)ethan-1-ol tribromide (1/1), C₄H₉NO·C₄H₁₀NO⁺·Br₃⁻ or [(C₄H₉NO)·(C₄H₁₀NO)](Br₃), (I), N,N-dimethylacetamide–1-(dimethyl-λ⁴-azanylidene)ethan-1-ol dibromidoiodate (1/1), C₄H₉NO·C₄H₁₀NO⁺·Br₂I⁻ or [(C₄H₉NO)·(C₄H₁₀NO)](Br₂I), (II), and N,N-dimethylacetamide–1-(dimethyl-λ⁴-azanylidene)ethan-1-ol dichloridoiodate (1/1), C₄H₉NO·C₄H₁₀NO⁺·Cl₂I⁻ or [(C₄H₉NO)·(C₄H₁₀NO)]·(Cl₂I), (III), all the anions are almost linear in geometry and all the cations, except for the methyl H atoms, are essentially planar. In the crystal structure of (I), the cations are linked by pairs of C—H⋯O hydrogen bonds, forming inversion dimers with an R₂²(8) ring motif. These dimers also exhibit O—H⋯O hydrogen bonding. Dimerized cation pairs and anions are arranged in columns along the a axis. In the crystal of (II), the cations are linked by pairs of O—H⋯O and C—H⋯O hydrogen bonds, forming an R₄⁴(14) ring motif. These groups of cations and the anions form individual columns along the a axis and jointly reside in planes roughly parallel to (011). In the crystal of (III), cations and anions also form columns parallel to the a axis, resulting in layers parallel to the (020) plane. Furthermore, the crystal structures of (I), (II) and (III) are consolidated by strong halogen (Br and/or I and/or Cl)⋯H and weak van der Waals interactions. In addition to the structural evaluation, a Hirshfeld surface analysis was carried out.

Keywords: crystal structure; dimethylacetamide; trihalide; hydrogen bond; Hirshfeld surface analysis.

CCDC references: 2271693; 2271692; 2271691

1. Chemical context

Halogenation is a chemical reaction that involves the introduction of one or more halogen atoms to an organic compound. Usually, either direct replacement of hydrogen by a halogen atom or addition of a halogen molecule to double and triple bonds are used. The pathway and stereochemistry of halogenation reactions are strongly dependent on the halogenating agent. However, halogens and interhalogens are very harmful to health. An effective source of active halogen should be a safe solid substance well soluble in different solvents, with a low pressure of halogen vapour and high content of the active halogen. As a source of halogens, molecular complexes with N- and O-nucleophiles are widely used. However, the N-halogen succinimides slowly decompose when stored and are poorly soluble in some solvents, while the molecular complexes of halogens with N- and O-nucleophiles (for instance, dioxane dibromide or complexes with pyridine) are short-lived (Abdell-Wahab et al., 1957 ; Horner et al., 1959 ; Zaugg et al., 1954 ; Buckles et al., 1957 ; Ramachandrappa et al., 1998 ; Groebel et al., 1960 ; Mohamed Farook et al., 2006 ; Sui et al., 2006 ). In this context, we synthesized inexpensive and readily available bis(N,N-dimethylacetamide) hydrogen trihalides as halogenation agents and source of positively charged halogen ions (Rodygin et al., 1992 ; Prokop'eva et al., 2008 ). The amide complexes with halogens are excellent reagents for the functionalization of phenols and anilines (Rodygin et al., 1992; Mikhailov et al., 1993 ; Safavora et al., 2019 ). They are also used in the synthesis of mono-halogen-substituted ketones (Rodygin et al., 1994a ; Burakov et al., 2001 ; Abdelhamid et al., 2011 ; Khalilov et al., 2021 ) and the halogenation of various alkenes, alkynes (Rodygin et al., 1994b ) and bridged epoxy-isoindolones (Zaytsev et al., 2017 ; Zubkov et al., 2018 ; Mertsalov et al., 2021a ,b ). The most famous amide complex, i.e. Povidone-iodine (PVP-I), also known as iodopovidone, is an antiseptic used for skin disinfection before and after surgery (Stuart et al., 2009 ). Moreover, noncovalent interactions play critical roles in synthesis and catalysis, as well as in forming supramolecular structures due to their significant contribution to the self-assembly process (Gurbanov et al., 2020a ,b , 2022a ,b ; Ma et al., 2017 , 2021 ; Mahmoudi et al., 2017a ,b ; Mahmudov et al., 2011 , 2022 ). Similar to hydrogen bonding, the halogen bond has also been used in the design of materials (Shikhaliyev et al., 2019 ). We, thus, analyzed such expected respective intermolecular interactions in the isolated and structurally characterized three title aggregates in the context of the present study.

2. Structural commentary

In the title compounds (I), (II) and (III) (Figs. 1, 2 and 3), the Br₃⁻, Br₂I⁻ and Cl₂I⁻ anions are almost or perfectly linear in geometry. For (I), Br1 resides in the centre of inversion symmetry [Br2—Br1—Br2(−x + 1, −y + 1, −z + 1) = 180.0°], with Br1—Br2 distances of 2.53725 (17) Å. The cations, except for their methyl H atoms, are essentially planar [r.m.s. deviation = 0.041 (1) Å for O1]. For (II), the angles and distances of the anion are Br1—I1—Br2 = 177.942 (5)°, I1—Br1 = 2.7244 (2) Å and I1—Br2 = 2.68597 (19) Å. These values are in agreement with data reported in the literature (Gardberg et al., 2002 ). The cations, except for their methyl H atoms, are again essentially planar [r.m.s. deviations = −0.018 (1) Å for O1 and −0.038 (2) Å for C7]. For (III), I1 resides in the centre of inversion symmetry [Cl1—I1—Cl1(−x + 1, −y + 1, −z + 1) = 180.0°], with distances of I1—Cl1 = 2.53973 (18) Å. The cations, except for their methyl H atoms, are planar and all reside on mirror planes.

Figure 1
The molecular structure of (I), with displacement ellipsoids for the non-H atoms drawn at the 50% probability level.

Figure 2
The molecular structure of (II), with displacement ellipsoids for the non-H atoms drawn at the 50% probability level. Symmetry codes: (_a) −x + 1, −y + 1, −z + 1; (_b) −x + 2, −y + 1, −z + 2.

Figure 3
The molecular structure of (III), with displacement ellipsoids for the non-H atoms drawn at the 50% probability level. Symmetry code: (_a) −x + 1, y, −z + 1.

In (I), (II) and (III), the O—C and N—C bond distances of the cation all fall between single and double bond values, with C1—N1 = 1.3134 (17) Å and C1—O1 = 1.2786 (16) Å for (I), C1—N1 = 1.3168 (16) Å, C5—N2 = 1.3121 (16) Å, C1—O1 = 1.2771 (15) Å and C5—O2 = 1.2794 (15) Å for (II), and C1—N1 = 1.3161 (8) Å and C1—O1 = 1.2750 (8) Å for (III). The corresponding bond lengths of the three compounds are in good agreement with each other and with the literature.

3. Supramolecular features and Hirshfeld surface analysis

In the crystal of (I), the cations are linked by pairs of C—H⋯O hydrogen bonds (symmetry code: −x + 2, −y + 1, −z + 2), forming inversion dimers with an R₂²(8) ring motif (Bernstein et al., 1995 ) (Table 1 and Fig. 4). These dimers also exhibit O—H⋯O hydrogen bonds (symmetry code: −x + 2, −y + 1, −z + 2). Dimerized cation pairs and anions are arranged in columns along the a axis (Figs. 4 and 5). In the crystal of (II), two cations are refined in the asymmetric unit. These cations are linked by pairs of O—H⋯O and C—H⋯O hydrogen bonds, forming an R₄⁴(14) ring motif (Table 2, and Figs. 6 and 7). The groups of cations and anions form columns along the a axis and reside in planes parallel to (011) (Figs. 6 and 7). In the crystal of (III), cations and anions are arranged in columns parallel to the a axis, forming layers parallel to the (020) plane (Table 3, and Figs. 8 and 9). Furthermore, the crystal structures of (I), (II) and (III) are consolidated by strong halogen (Br and/or I and/or Cl)⋯H bonding interactions, Coulombic attraction and weak van der Waals interactions (Tables 4 and 5) between the cations and anions in three dimensions.

Table 1
Hydrogen-bond geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1ⁱ	0.98	2.52	3.2622 (18)	132
C2—H2B⋯Br2ⁱⁱ	0.98	3.14	4.0788 (15)	162
C2—H2C⋯Br1ⁱⁱⁱ	0.98	3.13	3.9596 (14)	143
C3—H3A⋯Br2^iv	0.98	3.10	4.0216 (15)	158
C3—H3C⋯Br2	0.98	3.05	3.8847 (15)	143
O1—H1⋯O1ⁱ	1.21	1.21	2.4224 (15)	180
Symmetry codes: (i) ; (ii) ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) .

Table 2
Hydrogen-bond geometry (Å, °) for (II)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.75 (5)	1.69 (5)	2.4278 (13)	173 (4)
O2—H2⋯O1	0.85 (5)	1.59 (5)	2.4278 (14)	170 (4)
C2—H2A⋯O2	0.98	2.57	3.2872 (17)	130
C2—H2B⋯Br2	0.98	3.09	4.0105 (14)	158
C2—H2C⋯I1ⁱ	0.98	3.18	4.0838 (14)	155
C3—H3A⋯Br2ⁱⁱ	0.98	3.07	3.8153 (14)	134
C3—H3B⋯O2ⁱⁱⁱ	0.98	2.54	3.3481 (16)	140
C4—H4A⋯I1ⁱ	0.98	3.31	4.1081 (14)	140
C6—H6A⋯O1	0.98	2.64	3.3630 (16)	131
C6—H6C⋯Br1ⁱⁱ	0.98	3.06	3.7331 (14)	128
C7—H7B⋯Br1^iv	0.98	2.97	3.8980 (15)	159
C8—H8A⋯Br1^v	0.98	3.05	3.9722 (15)	157
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) x, y, z+1.

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1ⁱ	0.64 (3)	1.79 (3)	2.4261 (11)	170 (4)
C2—H2A⋯Cl1ⁱⁱ	0.98	2.93	3.7461 (8)	141
C2—H2A⋯O1ⁱ	0.98	2.61	3.3230 (9)	130
C2—H2C⋯Cl1	0.98	2.96	3.6902 (3)	132
C3—H3A⋯Cl1ⁱⁱⁱ	0.98	2.95	3.6479 (9)	129
C3—H3B⋯Cl1^iv	0.98	2.89	3.7897 (8)	153
C3—H3C⋯O1^v	0.98	2.65	3.6256 (4)	176
Symmetry codes: (i) ; (ii) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (iv) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (v) $[-x+{\script{3\over 2}}, -y-{\script{1\over 2}}, -z+2]$ .

Table 4
Summary of short interatomic contacts (Å) in (I), (II) and (III)

Contact	Distance	Symmetry operation
(I)
H1⋯O1	1.61	−x + 2, −y + 1, −z + 2
O1⋯H4B	2.73	x + $[{1\over 2}]$ , −y + $[{1\over 2}]$ , z + $[{1\over 2}]$
C2⋯H4C	3.06	−x + $[{3\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{3\over 2}]$
C2⋯H3B	3.09	x + $[{1\over 2}]$ , −y + $[{1\over 2}]$ , z − $[{1\over 2}]$
H2A⋯Br2	3.21	x + 1, y, z
H3C⋯Br2	3.05	x, y, z
H2C⋯Br1	3.13	−x + $[{3\over 2}]$ , y − $[{1\over 2}]$ , −z + $[{3\over 2}]$
H3A⋯Br2	3.09	−x + 1, −y + 1, −z + 2
H4C⋯Br2	3.23	−x + $[{1\over 2}]$ , y − $[{1\over 2}]$ , −z + $[{3\over 2}]$
Br2⋯H2B	3.14	−x + 1, −y + 1, −z + 1

(II)
H1⋯H2	0.86	x, y, z
C1⋯O1	3.24	−x, −y + 1, −z + 1
H3C⋯O1	2.68	−x + 1, −y + 1, −z + 1
H2A⋯H2A	2.54	−x, −y, −z + 1
H3C⋯Br2	3.23	x, y + 1, z
H2B⋯Br2	3.09	x, y, z
H2C⋯I1	3.18	x − 1, y, z
H3A⋯Br2	3.07	−x + 1, −y + 1, −z + 1
H3C⋯H6A	2.58	−x + 1, −y + 1, −z + 1
O2⋯H3B	2.54	−x, −y + 1, −z + 1
H8B⋯Br1	3.19	−x + 1, −y, −z + 1
H6C⋯Br1	3.06	−x + 1, −y + 1, −z + 1
H8A⋯Br1	3.05	x, y, z + 1
H7B⋯Br1	2.97	x − 1, y, z + 1

(III)
H1⋯O1	1.79	−x + 1, y, −z + 2
H3C⋯O1	2.65	−x + $[{3\over 2}]$ , y − $[{1\over 2}]$ , −z + 2
H4B⋯Cl1	3.00	x, y − 1, z
H2C⋯Cl1	2.96	x, y, z
C3⋯C3	2.60	−x + 2, y, −z + 2
H3A⋯Cl1	2.95	−x + $[{3\over 2}]$ , y − $[{1\over 2}]$ , −z + 2
H2A⋯Cl1	2.93	x − $[{1\over 2}]$ , y − $[{1\over 2}]$ , z
H2C⋯H4C	2.58	x − $[{1\over 2}]$ , y + $[{1\over 2}]$ , z
H3B⋯Cl1	2.89	x + $[{1\over 2}]$ , y − $[{1\over 2}]$ , z
I1⋯H4A	3.37	−x + 1, y, −z + 1
I1⋯H4C	3.36	−x + $[{3\over 2}]$ , y + $[{1\over 2}]$ , −z + 1

Table 5
Percentage contributions of interatomic contacts to the Hirshfeld surface for (I), (II) and (III)

Contact	(I) (%)	(II) (%)	(III) (%)
H⋯H	57.5	60.3	88.9
Br⋯H/H⋯Br	24.0	15.2	–
O⋯H/H⋯O	13.3	12.0	6.5
C⋯H/H⋯C	3.0	2.7	2.0
Br⋯N/N⋯Br	1.0	–	–
N⋯H/H⋯N	0.9	2.4	0.8
Br⋯C/C⋯Br	0.5	–	–
I⋯H/H⋯I	–	4.7	–
O⋯C/C⋯O	–	2.2	–
O⋯N/N⋯O	–	0.3	–
O⋯O	–	0.1	–
Cl⋯N/N⋯Cl	–	–	0.8
Cl⋯C/C⋯Cl	–	–	0.7
Cl⋯H/H⋯Cl	–	–	0.4

Figure 4
A view along the a axis of the O—H⋯O and C—H⋯O interactions in the crystal structure of (I)

Figure 5
A view along the c axis of the O—H⋯O and C—H⋯O interactions in the crystal structure of (I)

Figure 6
A view along the a axis of the O—H⋯O and C—H⋯O interactions in the crystal structure of (II)

Figure 7
A view along the b axis of the O—H⋯O and C—H⋯O interactions in the crystal structure of (II)

Figure 8
A view along the a axis of the O—H⋯O interactions in the crystal structure of (III)

Figure 9
A view along the c axis of the O—H⋯O interactions in the crystal structure of (III)

The O⋯O distances in (I), (II) and (III) are 2.4224 (15), 2.4278 (14) and 2.4261 (9) Å, respectivly, and are thereby within the range (2.31–2.63 Å) found for short/strong classical hydrogen bonds (Hussain & Schlemper, 1980 ; Behmel et al., 1981 ).

The Hirshfeld surface analysis and the associated two-dimensional fingerprint plots over the cations of (I), (II) and (III) were carried out and created with CrystalExplorer17.5 (Spackman et al., 2021 ). A summary of the short interatomic contacts in (I), (II) and (III) is given in Table 4. The two-dimensional fingerprint plots for compounds (I), (II) and (III) are shown in Fig. 10. The principal interatomic interactions for the title compound [Figs. 10(b)–(d) and Table 5] are delineated into H⋯H [57.5% for (I); 60.3% for (II); 88.9% for (III)], Br⋯H/H⋯Br [24.0% for (I); 15.2% for (II)], O⋯H/H⋯O [6.5% for (III)] and O⋯H/H⋯O [13.3% for (I); 12.0% for (II)] and C⋯H/H⋯C [2.0% for (III)] contacts.

Figure 10
A view of the two-dimensional fingerprint plots for compounds (I), (II) and (III), showing (a) all interactions, and separated into (b) H⋯H, (c) Br⋯H/H⋯Br for (I) and (II), O⋯H/H⋯O for (III) and (d) O⋯H/H⋯O for (I) and (II), C⋯H/H⋯C for (III) interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface contacts.

The respective differences in the crystal structures of the three title compounds [(I): space group, monoclinic P2₁/n, Z = 2; (II): space group, triclinic P $[\overline{1}]$ , Z = 2; (III): space group, monoclinic C2/m, Z = 2], may be the result of small deviations in the interactions arising from the different crystal systems and packing, as well as from the variations in the anions of the compounds.

4. Database survey

A database search was carried out using ConQUEST (Bruno et al., 2002 ), part of Version 2022.3.0 of the Cambridge Structural Database (Groom et al., 2016 ). A search for structures with the simultaneous presence of N,N-dimethylacetamide and its respective protonated form resulted in ten hits. Two compounds are deposited twice, so there are only eight related structures known. Compounds closely related to the title compound are: bis[hexakis(N,N-dimethylacetamide-κO)aluminium(III)] bis(N,N-dimethylacetamide)ium heptakis(perchlorate) (CSD refcode DEGBOH; Suzuki & Ishiguro, 2006 ), hydrogen bis(N,N-dimethylacetamide) tetrachlorogold(III) (HDMAAU; Hussain et al., 1980), hydrogen bis(dimethylacetamide) tribromide [SEGMOG (Gubin et al., 1988 ) and SEGMOG01 (Mikhailov et al., 1992 )].

In the crystal of DEGBOH (space group: monoclinic P2₁n, Z = 2), the Al³⁺ ion is surrounded by dma molecules (dma = dimethylacetamide) in an octahedral arrangement. The dma molecules are essentially planar. Three Al—O—C—N torsion angles [138.8 (8)–149.3 (4)°] are found to deviate significantly from 180°. The centrosymmetric cation has the bridging H atom at the centre of inversion. The planar structure is essentially the same as those reported for [H(dma)₂]⁺ cations; the O⋯O distance [2.386 (8) Å] is within the range (2.31–2.63 Å) found for short hydrogen bonds (Hussain & Schlemper, 1980; Behmel et al., 1981).

In the crystal of HDMAAU (space group: monoclinic P2₁a, Z = 2), the structure consists of distinct [AuCl₄]⁻ anions and [H(dma)₂]⁺ cations, with the gold and the bridging H atoms located at centres of symmetry. The hydrogen bond is `symmetrical' as a result of crystallographic requirements. The O⋯O distance is 2.430 (16) Å. Thermal motion analysis indicates that methyl groups attached to nitrogen have higher rotational amplitudes, resulting in short apparent C—H bond lengths [average 0.96 (4) Å] compared with the methyl group attached to a carbonyl C atom which has an average C—H bond length of 1.02 (2) Å.

In the crystal of SEGMOG (space group: monoclinic P2₁c, Z = 2), two N,N-dimethylacetamide molecules in the asymmetric unit are connected to each other by an O—H⋯O hydrogen bond, essentially sharing the central H atom. These molecules and the Br—Br—Br groups are arranged in columns parallel to the a axis. The arrangement is consolidated in the crystal packing by van der Waals interactions between these columns.

In the crystal of SEGMOG01 (space group: monoclinic P2₁n, Z = 2), the unit-cell parameters and the arrangement of the molecules are relatively similar to the older structure (SEGMOG), while the H atom bridging the the two acetamides was not refined.

5. Synthesis and crystallization

5.1. General procedure

To a solution of dimethylacetamide (9.28 ml, 0.1 mol) in 0.09 mol of 38% hydrochloric or 40% hydrobromic acid under stirring and cooling in an ice–water bath, 0.05 mol iodine monochloride (8.10 g, 0.05 mol), iodine monobromide (10.35 g, 0.05 mol) or bromine (4.00 g, 0.05 mol) was added gradually. The mixture was stirred for 1 h and the crystals were filtered off, dried and recrystallized from methanol to give the target bis(N,N-dimethylacetamide) hydrogen halides as orange colored solids. Single crystals of bis(N,N-dimethylacetamide) hydrogen halides were obtained by slow crystallization from methanol.

5.2. N,N-Dimethylacetamide–1-(dimethyl-λ⁴-azanylidene)ethan-1-ol tribromide (1/1), (I)

Bright orange crystals (Rodygin et al., 1992; Gubin et al., 1988), yield 81% (16.8 g), m.p. 361–362 K. IR (KBr), ν (cm⁻¹): 1664 (NCO). ¹H NMR (700.2 MHz, CDCl₃): δ (J, Hz) 12.51 (br s, 1H), 3.28 (s, 3H, NCH₃), 3.19 (s, 3H, NCH₃), 2.45 (s, 3H, CH₃); ¹³C{¹H} NMR (176 MHz, CDCl₃): δ 174.5, 39.7, 37.5, 19.9.

5.3. N,N-Dimethylacetamide–1-(dimethyl-λ⁴-azanylidene)ethan-1-ol dibromidoiodate (1/1), (II)

Bright-orange crystals, yield 44% (10.2 g), m.p. 343–344 K. IR (KBr), ν (cm⁻¹): 1606 (NCO). ¹H NMR (700.2 MHz, CDCl₃): δ (J, Hz) 10.72 (br s, 1H), 3.28 (s, 3H, NCH₃), 3.19 (s, 3H, NCH₃), 2.46 (s, 3H, CH₃); ¹³C{¹H} NMR (176 MHz, CDCl₃): δ 174.6, 39.6, 37.5, 20.1.

5.4. N,N-Dimethylacetamide–1-(dimethyl-λ⁴-azanylidene)ethan-1-ol dichloridoiodate (1/1), (III)

Bright orange crystals, yield 75% (14 g), m.p. 364–365 K. IR (KBr), ν (cm⁻¹): 1611 (NCO). ¹H NMR (700.2 MHz, CDCl₃): δ (J, Hz) 9.98 (br s, 1H), 3.25 (s, 3H, NCH₃), 3.17 (s, 3H, NCH₃), 2.41 (s, 3H, CH₃); ¹³C{¹H} NMR (176 MHz, CDCl₃): δ 174.2, 39.4, 37.2, 19.8.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 6. In compounds (I), (II) and (III), the C-bound H atoms were positioned geometrically, with C—H = 0.98 Å (for methyl H atoms), and constrained to ride on their parent atoms, with U_iso(H) = 1.5U_eq(C). The hydroxy H atoms were found in the difference Fourier maps and their coordinates were refined freely, with U_iso(H) = 1.5U_eq(O). In (I), the H atom of the OH group is located in a special position (1.0, 0.5, 1.0) with an occupancy of 0.5 for the rrefined atom. In (II), the H atoms of the OH groups are disordered over two positions, with occupancies of 0.49 and 0.51. In (III), the H atom of the OH group was refined with an occupancy of 0.25 for its position close to an inversion centre in between the O atoms of two acetamides and simultaneously residing on a mirror plane.

Table 6
Experimental details

For all structures: Z = 2. Experiments were carried out at 100 K with Mo Kα radiation using a Bruker Kappa APEXII area-detector diffractometer. Absorption was corrected for by multi-scan methods (SADABS; Bruker, 2008 ).

	(I)	(II)	(III)
Crystal data
Chemical formula	C₄H₉NO·C₄H₁₀NO⁺·Br₃⁻	C₄H₉NO·C₄H₁₀NO⁺·Br₂I⁻	C₄H₉NO·C₄H₁₀NO⁺·Cl₂I⁻
M_r	414.98	461.97	373.05
Crystal system, space group	Monoclinic, P2₁/n	Triclinic, P $[\overline{1}]$	Monoclinic, C2/m
a, b, c (Å)	7.9009 (4), 10.3466 (6), 9.4948 (5)	7.2943 (3), 7.9544 (4), 13.6097 (7)	10.5264 (3), 6.7261 (2), 10.8124 (3)
α, β, γ (°)	90, 107.703 (2), 90	90.645 (2), 103.651 (2), 93.656 (2)	90, 105.950 (1), 90
V (Å³)	739.42 (7)	765.51 (6)	736.06 (4)
μ (mm⁻¹)	8.17	7.30	2.53
Crystal size (mm)	0.24 × 0.20 × 0.14	0.14 × 0.08 × 0.06	0.20 × 0.18 × 0.14

Data collection
T_min, T_max	0.315, 0.394	0.515, 0.669	0.630, 0.719
No. of measured, independent and observed [I > 2σ(I)] reflections	11995, 3239, 2402	30601, 6766, 5446	13071, 1745, 1745
R_int	0.026	0.021	0.014
(sin θ/λ)_max (Å⁻¹)	0.807	0.811	0.811

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.056, 1.01	0.019, 0.038, 1.03	0.008, 0.022, 1.06
No. of reflections	3239	6766	1745
No. of parameters	73	149	52
H-atom treatment	H-atom parameters constrained	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)	0.43, −0.78	0.52, −0.62	0.46, −0.26
Computer programs: APEX2 and SAINT (Bruker, 2013 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC references: 2271693; 2271692; 2271691

Crystal structure: contains datablocks I, II, III, global. DOI: https://doi.org/10.1107/S2056989023005509/yz2034sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023005509/yz2034Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989023005509/yz2034IIsup3.hkl

Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989023005509/yz2034IIIsup4.hkl

checkCIF report

Computing details top

For all structures, data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

N,N-Dimethylacetamide–1-(dimethyl-λ⁴-azanylidene)ethan-1-ol tribromide (1/1) (I) top

Crystal data top

C₄H₉NO·C₄H₁₀NO⁺·Br₃⁻	F(000) = 404
M_r = 414.98	D_x = 1.864 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.9009 (4) Å	Cell parameters from 3187 reflections
b = 10.3466 (6) Å	θ = 3.0–34.7°
c = 9.4948 (5) Å	µ = 8.17 mm⁻¹
β = 107.703 (2)°	T = 100 K
V = 739.42 (7) Å³	Fragment, orange
Z = 2	0.24 × 0.20 × 0.14 mm

Data collection top

Bruker Kappa APEXII area-detector diffractometer	2402 reflections with I > 2σ(I)
ω– and φ–scans	R_int = 0.026
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θ_max = 35.0°, θ_min = 4.5°
T_min = 0.315, T_max = 0.394	h = −12→12
11995 measured reflections	k = −16→16
3239 independent reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.025	H-atom parameters constrained
wR(F²) = 0.056	w = 1/[σ²(F_o²) + (0.0249P)² + 0.0334P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.002
3239 reflections	Δρ_max = 0.43 e Å⁻³
73 parameters	Δρ_min = −0.78 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.

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

	x	y	z	U_iso*/U_eq
Br1	0.500000	0.500000	0.500000	0.01461 (5)
Br2	0.26135 (2)	0.50973 (2)	0.62805 (2)	0.02228 (5)
O1	0.85472 (13)	0.45244 (10)	0.98120 (11)	0.0190 (2)
H1	1.000000	0.500000	1.000000	0.029*
N1	0.66034 (15)	0.29961 (10)	0.87188 (13)	0.0153 (2)
C1	0.80749 (18)	0.36364 (12)	0.88341 (15)	0.0146 (2)
C2	0.91855 (19)	0.33325 (14)	0.78479 (16)	0.0193 (3)
H2A	1.028724	0.383619	0.816158	0.029*
H2B	0.852428	0.355410	0.682486	0.029*
H2C	0.947123	0.240846	0.791228	0.029*
C3	0.55467 (19)	0.32410 (14)	0.97137 (17)	0.0198 (3)
H3A	0.624789	0.374837	1.056242	0.030*
H3B	0.521000	0.241642	1.006057	0.030*
H3C	0.447312	0.372248	0.918561	0.030*
C4	0.5868 (2)	0.20268 (14)	0.75764 (17)	0.0214 (3)
H4A	0.658131	0.199738	0.689389	0.032*
H4B	0.464005	0.225520	0.703018	0.032*
H4C	0.589038	0.117778	0.803936	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01420 (9)	0.01516 (8)	0.01360 (8)	0.00133 (6)	0.00293 (7)	−0.00072 (6)
Br2	0.01914 (8)	0.02903 (8)	0.02132 (8)	0.00196 (6)	0.01013 (6)	−0.00041 (6)
O1	0.0217 (5)	0.0179 (4)	0.0149 (5)	−0.0066 (4)	0.0018 (4)	−0.0020 (4)
N1	0.0183 (6)	0.0141 (5)	0.0135 (5)	−0.0035 (4)	0.0050 (5)	−0.0023 (4)
C1	0.0168 (6)	0.0132 (5)	0.0116 (6)	0.0002 (5)	0.0009 (5)	0.0037 (4)
C2	0.0210 (7)	0.0196 (6)	0.0184 (7)	−0.0002 (5)	0.0078 (6)	0.0016 (5)
C3	0.0205 (7)	0.0214 (6)	0.0200 (7)	−0.0025 (5)	0.0098 (6)	−0.0021 (5)
C4	0.0255 (7)	0.0186 (6)	0.0191 (7)	−0.0073 (5)	0.0056 (6)	−0.0063 (5)

Geometric parameters (Å, º) top

Br1—Br2ⁱ	2.5372 (2)	C2—H2B	0.9800
Br1—Br2	2.5372 (2)	C2—H2C	0.9800
O1—C1	1.2786 (16)	C3—H3A	0.9800
O1—H1	1.2112	C3—H3B	0.9800
N1—C1	1.3134 (17)	C3—H3C	0.9800
N1—C3	1.4605 (18)	C4—H4A	0.9800
N1—C4	1.4618 (18)	C4—H4B	0.9800
C1—C2	1.4984 (19)	C4—H4C	0.9800
C2—H2A	0.9800

Br2ⁱ—Br1—Br2	180.0	H2B—C2—H2C	109.5
C1—O1—H1	116.95	N1—C3—H3A	109.5
C1—N1—C3	121.62 (11)	N1—C3—H3B	109.5
C1—N1—C4	123.36 (12)	H3A—C3—H3B	109.5
C3—N1—C4	115.00 (11)	N1—C3—H3C	109.5
O1—C1—N1	118.58 (12)	H3A—C3—H3C	109.5
O1—C1—C2	120.50 (12)	H3B—C3—H3C	109.5
N1—C1—C2	120.92 (12)	N1—C4—H4A	109.5
C1—C2—H2A	109.5	N1—C4—H4B	109.5
C1—C2—H2B	109.5	H4A—C4—H4B	109.5
H2A—C2—H2B	109.5	N1—C4—H4C	109.5
C1—C2—H2C	109.5	H4A—C4—H4C	109.5
H2A—C2—H2C	109.5	H4B—C4—H4C	109.5

C3—N1—C1—O1	−2.46 (19)	C3—N1—C1—C2	177.27 (12)
C4—N1—C1—O1	175.52 (13)	C4—N1—C1—C2	−4.8 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1ⁱⁱ	0.98	2.52	3.2622 (18)	132
C2—H2B···Br2ⁱ	0.98	3.14	4.0788 (15)	162
C2—H2C···Br1ⁱⁱⁱ	0.98	3.13	3.9596 (14)	143
C3—H3A···Br2^iv	0.98	3.10	4.0216 (15)	158
C3—H3C···Br2	0.98	3.05	3.8847 (15)	143
O1—H1···O1ⁱⁱ	1.21	1.21	2.4224 (15)	180
C3—H3A···O1	0.98	2.29	2.6940 (19)	104

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

N,N-Dimethylacetamide–1-(dimethyl-λ⁴-azanylidene)ethan-1-ol dibromidoiodate (1/1) (II) top

Crystal data top

C₄H₉NO·C₄H₁₀NO⁻·Br₂I⁻	Z = 2
M_r = 461.97	F(000) = 440
Triclinic, P1	D_x = 2.004 Mg m⁻³
a = 7.2943 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.9544 (4) Å	Cell parameters from 9984 reflections
c = 13.6097 (7) Å	θ = 2.9–35.2°
α = 90.645 (2)°	µ = 7.30 mm⁻¹
β = 103.651 (2)°	T = 100 K
γ = 93.656 (2)°	Fragment, orange
V = 765.51 (6) Å³	0.14 × 0.08 × 0.06 mm

Data collection top

Bruker Kappa APEXII area-detector diffractometer	5446 reflections with I > 2σ(I)
ω– and φ–scans	R_int = 0.021
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θ_max = 35.2°, θ_min = 4.3°
T_min = 0.515, T_max = 0.669	h = −11→11
30601 measured reflections	k = −12→12
6766 independent reflections	l = −22→21

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.019	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.038	w = 1/[σ²(F_o²) + (0.0119P)² + 0.2374P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
6766 reflections	Δρ_max = 0.52 e Å⁻³
149 parameters	Δρ_min = −0.62 e Å⁻³
0 restraints

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
I1	0.65027 (2)	0.18015 (2)	0.21358 (2)	0.01710 (2)
Br1	0.80118 (2)	0.33097 (2)	0.06912 (2)	0.02346 (3)
Br2	0.51412 (2)	0.02963 (2)	0.35979 (2)	0.02157 (3)
O1	0.20994 (14)	0.43799 (12)	0.57436 (7)	0.01964 (19)
H1	0.187 (6)	0.388 (6)	0.617 (3)	0.029*	0.49 (4)
O2	0.10583 (13)	0.27819 (13)	0.70454 (7)	0.02121 (19)
H2	0.151 (5)	0.325 (6)	0.659 (3)	0.032*	0.51 (4)
N1	0.22672 (15)	0.45877 (13)	0.41323 (8)	0.01563 (19)
N2	0.14789 (15)	0.19762 (14)	0.86403 (8)	0.0168 (2)
C1	0.17805 (16)	0.37110 (15)	0.48569 (9)	0.0147 (2)
C2	0.08734 (19)	0.19621 (16)	0.46499 (10)	0.0204 (2)
H2A	0.080500	0.143984	0.529020	0.031*
H2B	0.162652	0.129403	0.430349	0.031*
H2C	−0.040553	0.200696	0.422060	0.031*
C3	0.31786 (18)	0.62905 (16)	0.43360 (10)	0.0198 (2)
H3A	0.354648	0.651700	0.506798	0.030*
H3B	0.229380	0.711180	0.401612	0.030*
H3C	0.430563	0.638270	0.406042	0.030*
C4	0.1909 (2)	0.39725 (18)	0.30812 (10)	0.0215 (3)
H4A	0.104320	0.295852	0.298507	0.032*
H4B	0.310488	0.370162	0.292695	0.032*
H4C	0.134030	0.484580	0.262824	0.032*
C5	0.21588 (17)	0.26890 (15)	0.79243 (9)	0.0155 (2)
C6	0.41829 (18)	0.33486 (16)	0.81159 (10)	0.0192 (2)
H6A	0.438604	0.396328	0.752644	0.029*
H6B	0.500151	0.240498	0.823484	0.029*
H6C	0.448650	0.410935	0.871198	0.029*
C7	−0.0468 (2)	0.12246 (19)	0.84285 (11)	0.0243 (3)
H7A	−0.107738	0.135459	0.771288	0.036*
H7B	−0.117410	0.179306	0.884927	0.036*
H7C	−0.045456	0.002396	0.858179	0.036*
C8	0.2581 (2)	0.18213 (19)	0.96814 (10)	0.0236 (3)
H8A	0.382190	0.242901	0.976432	0.035*
H8B	0.274782	0.062886	0.982492	0.035*
H8C	0.191026	0.230260	1.015097	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01763 (4)	0.01708 (3)	0.01549 (4)	0.00366 (3)	0.00121 (3)	−0.00183 (3)
Br1	0.02527 (7)	0.02855 (7)	0.01748 (7)	0.00332 (5)	0.00655 (5)	−0.00017 (5)
Br2	0.02328 (7)	0.01921 (6)	0.02211 (7)	0.00054 (5)	0.00536 (5)	0.00173 (5)
O1	0.0235 (5)	0.0221 (4)	0.0133 (4)	0.0003 (4)	0.0045 (4)	0.0014 (3)
O2	0.0171 (4)	0.0323 (5)	0.0145 (4)	0.0026 (4)	0.0038 (4)	0.0061 (4)
N1	0.0139 (5)	0.0185 (4)	0.0143 (5)	0.0007 (4)	0.0031 (4)	0.0021 (4)
N2	0.0175 (5)	0.0207 (5)	0.0125 (5)	0.0015 (4)	0.0040 (4)	0.0017 (4)
C1	0.0113 (5)	0.0178 (5)	0.0146 (5)	0.0026 (4)	0.0020 (4)	0.0022 (4)
C2	0.0220 (6)	0.0181 (5)	0.0202 (6)	−0.0019 (5)	0.0039 (5)	0.0016 (5)
C3	0.0168 (6)	0.0189 (5)	0.0227 (6)	−0.0016 (4)	0.0030 (5)	0.0038 (5)
C4	0.0237 (7)	0.0266 (6)	0.0148 (6)	0.0022 (5)	0.0059 (5)	0.0006 (5)
C5	0.0164 (5)	0.0161 (5)	0.0149 (5)	0.0043 (4)	0.0047 (4)	0.0006 (4)
C6	0.0182 (6)	0.0213 (5)	0.0180 (6)	0.0003 (4)	0.0043 (5)	0.0013 (5)
C7	0.0194 (6)	0.0337 (7)	0.0208 (7)	−0.0019 (5)	0.0075 (5)	0.0031 (5)
C8	0.0270 (7)	0.0292 (7)	0.0133 (6)	0.0001 (5)	0.0027 (5)	0.0039 (5)

Geometric parameters (Å, º) top

I1—Br2	2.6860 (2)	C3—H3A	0.9800
I1—Br1	2.7243 (2)	C3—H3B	0.9800
O1—C1	1.2771 (15)	C3—H3C	0.9800
O1—H1	0.75 (5)	C4—H4A	0.9800
O2—C5	1.2794 (15)	C4—H4B	0.9800
O2—H2	0.85 (5)	C4—H4C	0.9800
N1—C1	1.3168 (16)	C5—C6	1.4965 (18)
N1—C3	1.4640 (16)	C6—H6A	0.9800
N1—C4	1.4648 (17)	C6—H6B	0.9800
N2—C5	1.3121 (16)	C6—H6C	0.9800
N2—C8	1.4656 (17)	C7—H7A	0.9800
N2—C7	1.4673 (17)	C7—H7B	0.9800
C1—C2	1.4961 (17)	C7—H7C	0.9800
C2—H2A	0.9800	C8—H8A	0.9800
C2—H2B	0.9800	C8—H8B	0.9800
C2—H2C	0.9800	C8—H8C	0.9800

Br2—I1—Br1	177.942 (6)	H4A—C4—H4B	109.5
C1—O1—H1	120 (3)	N1—C4—H4C	109.5
C5—O2—H2	118 (3)	H4A—C4—H4C	109.5
C1—N1—C3	120.94 (11)	H4B—C4—H4C	109.5
C1—N1—C4	123.49 (11)	O2—C5—N2	118.46 (12)
C3—N1—C4	115.55 (10)	O2—C5—C6	120.28 (11)
C5—N2—C8	123.75 (11)	N2—C5—C6	121.25 (11)
C5—N2—C7	120.94 (11)	C5—C6—H6A	109.5
C8—N2—C7	115.28 (11)	C5—C6—H6B	109.5
O1—C1—N1	118.77 (11)	H6A—C6—H6B	109.5
O1—C1—C2	120.38 (11)	C5—C6—H6C	109.5
N1—C1—C2	120.84 (11)	H6A—C6—H6C	109.5
C1—C2—H2A	109.5	H6B—C6—H6C	109.5
C1—C2—H2B	109.5	N2—C7—H7A	109.5
H2A—C2—H2B	109.5	N2—C7—H7B	109.5
C1—C2—H2C	109.5	H7A—C7—H7B	109.5
H2A—C2—H2C	109.5	N2—C7—H7C	109.5
H2B—C2—H2C	109.5	H7A—C7—H7C	109.5
N1—C3—H3A	109.5	H7B—C7—H7C	109.5
N1—C3—H3B	109.5	N2—C8—H8A	109.5
H3A—C3—H3B	109.5	N2—C8—H8B	109.5
N1—C3—H3C	109.5	H8A—C8—H8B	109.5
H3A—C3—H3C	109.5	N2—C8—H8C	109.5
H3B—C3—H3C	109.5	H8A—C8—H8C	109.5
N1—C4—H4A	109.5	H8B—C8—H8C	109.5
N1—C4—H4B	109.5

C3—N1—C1—O1	0.75 (17)	C8—N2—C5—O2	−178.76 (12)
C4—N1—C1—O1	−177.75 (11)	C7—N2—C5—O2	3.09 (18)
C3—N1—C1—C2	−179.15 (11)	C8—N2—C5—C6	2.56 (19)
C4—N1—C1—C2	2.35 (18)	C7—N2—C5—C6	−175.59 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.75 (5)	1.69 (5)	2.4278 (13)	173 (4)
O2—H2···O1	0.85 (5)	1.59 (5)	2.4278 (14)	170 (4)
C2—H2A···O2	0.98	2.57	3.2872 (17)	130
C2—H2B···Br2	0.98	3.09	4.0105 (14)	158
C2—H2C···I1ⁱ	0.98	3.18	4.0838 (14)	155
C3—H3A···Br2ⁱⁱ	0.98	3.07	3.8153 (14)	134
C3—H3B···O2ⁱⁱⁱ	0.98	2.54	3.3481 (16)	140
C4—H4A···I1ⁱ	0.98	3.31	4.1081 (14)	140
C6—H6A···O1	0.98	2.64	3.3630 (16)	131
C6—H6C···Br1ⁱⁱ	0.98	3.06	3.7331 (14)	128
C7—H7B···Br1^iv	0.98	2.97	3.8980 (15)	159
C8—H8A···Br1^v	0.98	3.05	3.9722 (15)	157
C3—H3A···O1	0.98	2.26	2.6878 (16)	105
C7—H7A···O2	0.98	2.24	2.6801 (18)	106

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

N,N-Dimethylacetamide–1-(dimethyl-λ⁴-azanylidene)ethan-1-ol dichloridoiodate (1/1) (III) top

Crystal data top

C₄H₉NO·C₄H₁₀NO⁻·Cl₂I⁻	F(000) = 368
M_r = 373.05	D_x = 1.683 Mg m⁻³
Monoclinic, C2/m	Mo Kα radiation, λ = 0.71073 Å
a = 10.5264 (3) Å	Cell parameters from 9986 reflections
b = 6.7261 (2) Å	θ = 3.6–35.1°
c = 10.8124 (3) Å	µ = 2.53 mm⁻¹
β = 105.950 (1)°	T = 100 K
V = 736.06 (4) Å³	Fragment, orange
Z = 2	0.20 × 0.18 × 0.14 mm

Data collection top

Bruker Kappa APEXII area-detector diffractometer	1745 reflections with I > 2σ(I)
ω– and φ–scans	R_int = 0.014
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θ_max = 35.2°, θ_min = 4.4°
T_min = 0.630, T_max = 0.719	h = −16→16
13071 measured reflections	k = −10→10
1745 independent reflections	l = −17→16

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.008	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.022	w = 1/[σ²(F_o²) + (0.0153P)² + 0.0381P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.003
1745 reflections	Δρ_max = 0.46 e Å⁻³
52 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
I1	0.500000	0.500000	0.500000	0.01617 (2)
Cl1	0.60222 (2)	0.500000	0.74187 (2)	0.02093 (3)
O1	0.60066 (6)	0.000000	0.96603 (6)	0.02505 (10)
H1	0.543 (3)	0.000000	0.977 (3)	0.038*	0.5
N1	0.70175 (6)	0.000000	0.81090 (6)	0.01741 (9)
C1	0.59151 (7)	0.000000	0.84597 (6)	0.01742 (10)
C2	0.45979 (7)	0.000000	0.74807 (8)	0.02291 (12)
H2A	0.390193	−0.021971	0.790959	0.034*	0.5
H2B	0.457166	−0.106447	0.685527	0.034*	0.5
H2C	0.445707	0.128418	0.703565	0.034*	0.5
C3	0.82909 (8)	0.000000	0.90856 (8)	0.02547 (13)
H3A	0.824028	0.085866	0.980273	0.038*	0.5
H3B	0.897594	0.049926	0.870861	0.038*	0.5
H3C	0.851076	−0.135792	0.940046	0.038*	0.5
C4	0.70493 (8)	0.000000	0.67698 (7)	0.02212 (12)
H4A	0.622560	0.056849	0.623015	0.033*	0.5
H4B	0.714477	−0.136724	0.649508	0.033*	0.5
H4C	0.779897	0.079874	0.668365	0.033*	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01526 (3)	0.01688 (3)	0.01778 (3)	0.000	0.00693 (2)	0.000
Cl1	0.02127 (7)	0.02325 (7)	0.01802 (6)	0.000	0.00499 (5)	0.000
O1	0.0226 (2)	0.0357 (3)	0.0204 (2)	0.000	0.01195 (19)	0.000
N1	0.0170 (2)	0.0189 (2)	0.0187 (2)	0.000	0.00881 (18)	0.000
C1	0.0173 (2)	0.0164 (2)	0.0208 (2)	0.000	0.0090 (2)	0.000
C2	0.0176 (3)	0.0254 (3)	0.0260 (3)	0.000	0.0065 (2)	0.000
C3	0.0172 (3)	0.0356 (4)	0.0242 (3)	0.000	0.0067 (2)	0.000
C4	0.0235 (3)	0.0260 (3)	0.0201 (3)	0.000	0.0113 (2)	0.000

Geometric parameters (Å, º) top

I1—Cl1	2.5398 (2)	C2—H2Cⁱⁱ	0.980 (10)
I1—Cl1ⁱ	2.5398 (2)	C3—H3A	0.9800
O1—C1	1.2750 (8)	C3—H3B	0.9800
O1—H1	0.64 (3)	C3—H3C	0.9800
N1—C1	1.3161 (8)	C3—H3Aⁱⁱ	0.980 (9)
N1—C4	1.4576 (9)	C3—H3Bⁱⁱ	0.980 (6)
N1—C3	1.4608 (10)	C3—H3Cⁱⁱ	0.980 (3)
C1—C2	1.4955 (10)	C4—H4A	0.9800
C2—H2A	0.9800	C4—H4B	0.9800
C2—H2B	0.9800	C4—H4C	0.9800
C2—H2C	0.9800	C4—H4Aⁱⁱ	0.980 (7)
C2—H2Aⁱⁱ	0.980 (5)	C4—H4Bⁱⁱ	0.9800 (17)
C2—H2Bⁱⁱ	0.980 (15)	C4—H4Cⁱⁱ	0.980 (8)

Cl1—I1—Cl1ⁱ	180.0	H3A—C3—H3Aⁱⁱ	72.2
C1—O1—H1	112 (3)	H3B—C3—H3Aⁱⁱ	137.5
C1—N1—C4	123.30 (6)	H3C—C3—H3Aⁱⁱ	40.1
C1—N1—C3	119.89 (6)	N1—C3—H3Bⁱⁱ	109.47 (14)
C4—N1—C3	116.81 (6)	H3A—C3—H3Bⁱⁱ	137.5
O1—C1—N1	117.87 (7)	H3B—C3—H3Bⁱⁱ	40.1
O1—C1—C2	121.10 (6)	H3C—C3—H3Bⁱⁱ	72.2
N1—C1—C2	121.02 (6)	H3Aⁱⁱ—C3—H3Bⁱⁱ	109.5
C1—C2—H2A	109.5	N1—C3—H3Cⁱⁱ	109.47 (6)
C1—C2—H2B	109.5	H3A—C3—H3Cⁱⁱ	40.1
H2A—C2—H2B	109.5	H3B—C3—H3Cⁱⁱ	72.2
C1—C2—H2C	109.5	H3C—C3—H3Cⁱⁱ	137.5
H2A—C2—H2C	109.5	H3Aⁱⁱ—C3—H3Cⁱⁱ	109.5
H2B—C2—H2C	109.5	H3Bⁱⁱ—C3—H3Cⁱⁱ	109.5
C1—C2—H2Aⁱⁱ	109.47 (11)	N1—C4—H4A	109.5
H2B—C2—H2Aⁱⁱ	123.6	N1—C4—H4B	109.5
H2C—C2—H2Aⁱⁱ	93.9	H4A—C4—H4B	109.5
C1—C2—H2Bⁱⁱ	109.5 (3)	N1—C4—H4C	109.5
H2A—C2—H2Bⁱⁱ	123.6	H4A—C4—H4C	109.5
H2B—C2—H2Bⁱⁱ	93.9	H4B—C4—H4C	109.5
H2C—C2—H2Bⁱⁱ	17.3	N1—C4—H4Aⁱⁱ	109.47 (15)
H2Aⁱⁱ—C2—H2Bⁱⁱ	109.5	H4A—C4—H4Aⁱⁱ	45.9
C1—C2—H2Cⁱⁱ	109.5 (2)	H4B—C4—H4Aⁱⁱ	66.5
H2A—C2—H2Cⁱⁱ	93.9	H4C—C4—H4Aⁱⁱ	139.6
H2B—C2—H2Cⁱⁱ	17.3	N1—C4—H4Bⁱⁱ	109.47 (3)
H2C—C2—H2Cⁱⁱ	123.6	H4A—C4—H4Bⁱⁱ	66.5
H2Aⁱⁱ—C2—H2Cⁱⁱ	109.5	H4B—C4—H4Bⁱⁱ	139.6
H2Bⁱⁱ—C2—H2Cⁱⁱ	109.5	H4C—C4—H4Bⁱⁱ	45.9
N1—C3—H3A	109.5	H4Aⁱⁱ—C4—H4Bⁱⁱ	109.5
N1—C3—H3B	109.5	N1—C4—H4Cⁱⁱ	109.47 (18)
H3A—C3—H3B	109.5	H4A—C4—H4Cⁱⁱ	139.6
N1—C3—H3C	109.5	H4B—C4—H4Cⁱⁱ	45.9
H3A—C3—H3C	109.5	H4C—C4—H4Cⁱⁱ	66.5
H3B—C3—H3C	109.5	H4Aⁱⁱ—C4—H4Cⁱⁱ	109.5
N1—C3—H3Aⁱⁱ	109.5 (2)	H4Bⁱⁱ—C4—H4Cⁱⁱ	109.5

C4—N1—C1—O1	180.000 (1)	C4—N1—C1—C2	0.000 (1)
C3—N1—C1—O1	0.000 (1)	C3—N1—C1—C2	180.000 (1)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1ⁱⁱⁱ	0.64 (3)	1.79 (3)	2.4261 (11)	170 (4)
C2—H2A···Cl1^iv	0.98	2.93	3.7461 (8)	141
C2—H2A···O1ⁱⁱⁱ	0.98	2.61	3.3230 (9)	130
C2—H2C···Cl1	0.98	2.96	3.6902 (3)	132
C3—H3A···Cl1^v	0.98	2.95	3.6479 (9)	129
C3—H3B···Cl1^vi	0.98	2.89	3.7897 (8)	153
C3—H3C···O1^vii	0.98	2.65	3.6256 (4)	176

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

Summary of short interatomic contacts (Å) in (I), (II) and (III) top

Contact	Distance	Symmetry operation
(I)
H1···O1	1.61	-x+2, -y+1, -z+2
O1···H4B	2.73	x+1/2, -y+1/2, z+1/2
C2···H4C	3.06	-x+3/2, y+1/2, -z+3/2
C2···H3B	3.09	x+1/2, -y+1/2, z-1/2
H2A···Br2	3.21	x+1, y, z
H3C···Br2	3.05	x, y, z
H2C···Br1	3.13	-x+3/2, y-1/2, -z+3/2
H3A···Br2	3.09	-x+1, -y+1, -z+2
H4C···Br2	3.23	-x+1/2, y-1/2, -z+3/2
Br2···H2B	3.14	-x+1, -y+1, -z+1

(II)
H1···H2	0.86	x, y, z
C1···O1	3.24	-x, -y+1, -z+1
H3C···O1	2.68	-x+1, -y+1, -z+1
H2A···H2A	2.54	-x, -y, -z+1
H3C···Br2	3.23	x, y+1, z
H2B···Br2	3.09	x, y, z
H2C···I1	3.18	x-1, y, z
H3A···Br2	3.07	-x+1, -y+1, -z+1
H3C···H6A	2.58	-x+1, -y+1, -z+1
O2···H3B	2.54	-x, -y+1, -z+1
H8B···Br1	3.19	-x+1, -y, -z+1
H6C···Br1	3.06	-x+1, -y+1, -z+1
H8A···Br1	3.05	x, y, z+1
H7B···Br1	2.97	x-1, y, z+1

(III)
H1···O1	1.79	-x+1, y, -z+2
H3C···O1	2.65	-x+3/2, y-1/2, -z+2
H4B···Cl1	3.00	x, y-1, z
H2C···Cl1	2.96	x, y, z
C3···C3	2.60	-x+2, y, -z+2
H3A···Cl1	2.95	-x+3/2, y-1/2, -z+2
H2A···Cl1	2.93	x-1/2, y-1/2, z
H2C···H4C	2.58	x-1/2, y+1/2, z
H3B···Cl1	2.89	x+1/2, y-1/2, z
I1···H4A	3.37	-x+1, y, -z+1
I1···H4C	3.36	-x+3/2, y+1/2, -z+1

Percentage contributions of interatomic contacts to the Hirshfeld surface for (I), (II) and (III) top

Contact	(I) (%)	(II) (%)	(III) (%)
H···H	57.5	60.3	88.9
Br···H/H···Br	24.0	15.2	-
O···H/H···O	13.3	12.0	6.5
C···H/H···C	3.0	2.7	2.0
Br···N/N···Br	1.0	-	-
N···H/H···N	0.9	2.4	0.8
Br···C/C···Br	0.5	-	-
I···H/H···I	-	4.7	-
O···C/C···O	-	2.2	-
O···N/N···O	-	0.3	-
O···O	-	0.1	-
Cl···N/N···Cl	-	-	0.8
Cl···C/C···Cl	-	-	0.7
Cl···H/H···Cl	-	-	0.4

Acknowledgements

The contributions of the authors are as follows: conceptualization, MA and AB; synthesis, DFM, DMS and MSG; X-ray analysis, GZM, MA, and SÖY; writing (review and editing of the manuscript) MA and AB; funding acquisition, GZM, DFM, DMS and MSG; supervision, MA and AB.

Funding information

GMZ thanks Baku State University for financial support. This publication was supported by the Russian Science Foundation (https://rscf.ru/project/22-73-00127/).

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 79| Part 8| August 2023| Pages 690-697

https://doi.org/10.1107/S2056989023005509

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

1. Chemical context

2. Structural commentary

3. Supra­molecular features and Hirshfeld surface analysis

4. Database survey

5. Synthesis and crystallization

5.1. General procedure

5.2. N,N-Di­methyl­acetamide–1-(dimethyl-λ4-aza­nyl­idene)ethan-1-ol tribromide (1/1), (I)

5.3. N,N-Di­methyl­acetamide–1-(dimethyl-λ4-aza­nyl­idene)ethan-1-ol di­bromido­iodate (1/1), (II)

5.4. N,N-Di­methyl­acetamide–1-(dimethyl-λ4-aza­nyl­idene)ethan-1-ol di­chlorido­iodate (1/1), (III)

6. Refinement

Supporting information

Acknowledgements

Funding information

References

research communications

3. Supramolecular features and Hirshfeld surface analysis

5.2. N,N-Dimethylacetamide–1-(dimethyl-λ⁴-azanylidene)ethan-1-ol tribromide (1/1), (I)

5.3. N,N-Dimethylacetamide–1-(dimethyl-λ⁴-azanylidene)ethan-1-ol dibromidoiodate (1/1), (II)

5.4. N,N-Dimethylacetamide–1-(dimethyl-λ⁴-azanylidene)ethan-1-ol dichloridoiodate (1/1), (III)