Abstract
C3H9Cl2N, monoclinic, I2/a (no. 15), a = 8.7694(5) Å, b = 9.6963(6) Å, c = 14.8577(9) Å, β = 98.266(3)°, V = 1250.24(13) Å3, Z = 8, Rgt(F) = 0.0193, wRref(F2) = 0.0511, T = 200 K.
The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Data collection and handling.
Crystal: | Colourless platelet |
Size: | 0.42 × 0.41 × 0.39 mm |
Wavelength: | Mo Kα radiation (0.71073 Å) |
μ: | 0.91 mm−1 |
Diffractometer, scan mode: | Bruker APEX-II, φ and ω |
θmax, completeness: | 28.4°, >99% |
N(hkl)measured, N(hkl)unique, Rint: | 5906, 1560, 0.011 |
Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 1483 |
N(param)refined: | 67 |
Programs: | Bruker [1], [2], SHELX [3], WinGX/ORTEP [4], Mercury [5], PLATON [6] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
Atom | x | y | z | Uiso*/Ueq |
---|---|---|---|---|
Cl1 | 0.61530 (3) | 0.52982 (3) | 0.12230 (2) | 0.03503 (9) |
N1 | 0.40081 (10) | 0.17699 (9) | 0.16933 (6) | 0.02508 (17) |
H711 | 0.2992 (19) | 0.1596 (15) | 0.1652 (10) | 0.041 (4)* |
H712 | 0.4264 (17) | 0.2321 (16) | 0.2143 (10) | 0.040 (4)* |
H713 | 0.4478 (17) | 0.0911 (16) | 0.1809 (10) | 0.040 (4)* |
C1 | 0.43768 (11) | 0.23458 (11) | 0.08204 (7) | 0.0273 (2) |
H1A | 0.386245 | 0.325109 | 0.070845 | 0.033* |
H1B | 0.396437 | 0.172162 | 0.031636 | 0.033* |
C2 | 0.60956 (12) | 0.25245 (12) | 0.08250 (7) | 0.0297(2) |
H2A | 0.660164 | 0.162244 | 0.096840 | 0.036* |
H2B | 0.627344 | 0.278402 | 0.020406 | 0.036* |
C3 | 0.68722 (11) | 0.35840 (11) | 0.14845 (8) | 0.0290 (2) |
H3A | 0.799623 | 0.356712 | 0.146663 | 0.035* |
H3B | 0.670062 | 0.333828 | 0.210888 | 0.035* |
Cl2 | 0.04089 (3) | 0.12061 (2) | 0.15846 (2) | 0.02772 (8) |
Source of material
The compound was obtained commercially (Fluka). Crystals suitable for the diffraction study were taken directly from the provided product.
Experimental details
Carbon-bound H atoms were placed in calculated positions (C–H 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C).
All three nitrogen-bound H atoms were located on a difference Fourier map and refined freely.
Comment
The effect of size and steric pretense of large ions on chemical and spectroscopic properties of compounds have been a focus of research for many decades and have been reported to influence the glass transition temperature in ionomers [7], surfactant modifying properties [8], the charge transfer in radical ions [9] and polymer-modified electrodes [10], as well as the structural and vibrational spectroscopic behaviour of DNA building blocks [11]. Furthermore, the benefit of choosing the adequate size of counterions to crystallize ionic compounds has been confirmed and reviewed on many occasions [12]. In continuation of our interest in metrical features of large cations [13], [14], [15], [16], [17], [18], [19] the structure of the title compound has been determined.
In the title compound, the C–Cl as well as the C–N bond lengths of 1.8003(11) and 1.4896(13) Å, respectively, are in good agreement with other primary ammonium salts and compounds featuring chloromethylene moieties whose metrical parameters have been deposited with the Cambridge Structural Database [20].
In the crystal, classical hydrogen bonds of the N–H…Cl type are observed with all of the pnicogen-bound hydrogen atoms acting as donors. In terms of graph-set analysis [21], [22], the descriptor for these hydrogen bonds is DDD at the unary level. In total, the entities of the crystal structure are connected to double layers perpendicular to the crystallographic c axis.
Funding source: National Research Foundation
Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: National Research Foundation.
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
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© 2020 Kina Muller et al., published by De Gruyter, Berlin/Boston
This work is licensed under the Creative Commons Attribution 4.0 International License.
Artikel in diesem Heft
- Frontmatter
- New Crystal Structures
- The crystal structure of 4-hydroxybenzene-1,3-diaminium dichloride, C6H10Cl2N2O
- The crystal structure of 3-chloropropylammonium chloride, C3H9Cl2N
- The crystal structure of 1-chloro-2-(dimethylamino)ethane hydrochloride, C4H11Cl2N
- Crystal structure of N-(2-(trifluoromethyl)phenyl)hexanamide, C13H16F3NO
- Redetermination of the crystal structure of para-toluidine, C7H9N
- The crystal structure of bis(1,3-dihydroxy-2-methylpropan-2-aminium) carbonate, C9H24N2O7
- The crystal structure of 4-chloro-1-methylpiperidin-1-ium chloride, C6H13Cl2N
- Crystal structure of (Z)-3-(6-bromo-1H-indol-3-yl)-1,3-diphenylprop-2-en-1-one, C23H16BrNO
- The crystal structure of ethyl 2-amino-4-(3,5-difluorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C20H21F2NO4
- Crystal structure of 6,6'‐((1E,1'E)‐(propane‐1,3‐diylbis(azaneylylidene))bis(methaneylylidene))bis(3‐bromophenol), C34H32Br4N4O4
- The crystal structure of (E)-2-(2-((2-picolinoylhydrazono)methyl)phenoxy)acetic acid dihydrate, C15H17N3O6
- Crystal structure of (E)-4-bromo-N′-(3-chloro-2-hydroxybenzylidene)benzohydrazide, C14H10BrClN2O2
- Crystal structure of N,N′-bis(4-bromosalicylidene) ethylene-1,2-diaminopropan, C34H32Br4N4O4
- Crystal structure of 4-bromo-N′-[(3-bromo-2-hydroxyphenyl)methylidene]benzohydrazide methanol solvate, C15H14Br2N2O3
- The crystal structure of 1,2-bis(1H-benzo[d]imidazol-2-yl)ethane-1,2-diol — N-(2-aminophenyl)-3-(1H-benzo[d]imidazol-2-yl)-2,3-dihydroxypropanamide (1/1), C32H30N8O5
- The crystal structure of para-trifluoromethyl-aniline hemihydrate, C14H14F6N2O
- Redetermination of the crystal structure of 2-amino-2-methyl-propane-1,3-diole, C4H11NO2
- The crystal structure of methacholine chloride, C8H18ClNO2
- Crystal structure of 5,7,7-trimethyl-4,6,7,8-tetrahydrocyclopenta[g]isochromen-1(3H)-one, C15H18O2
- Crystal structure of poly[diammine-bis(μ4-4-hydroxypyridine-3-sulfonato-κ5N:O, O′:O′′:O′′)(μ2-pyrazinyl-κ2N:N′)tetrasilver(I)], C7H8Ag2N3O4S
- Crystal structure of ethyl (E)-5-(((3′,6′-bis(ethylamino)-3-oxospiro[isoindoline-1,9′-xanthen]-2-yl)imino)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylate — ethanol (1/1), C38H45N5O5
- Crystal structure of 4-bromo-N′-[(3-chloro-2-hydroxyphenyl)methylidene]benzohydrazide, C14H7Br2N2O2
- Redetermination of the crystal structure of 3,3,3-triphenylpropanoic acid, C21H18O2 – Deposition of hydrogen atomic coordinates
- Structure redetermination of dextromethorphan hydrobromide monohydrate, C18H28BrNO2 – localization of hydrogen atoms
- Crystal structure of tris(azido-κ1N)-(N-(2-aminoethyl)-N-methyl-1,3-propanediamine-κ3N,N′,N′′)cobalt(III), C7H19CoN12
- Crystal structure of tetraaqua-bis(1H-indazole-6-carboxylate-κN)cadmium (II), C16H18CdN4O8
- Crystal structure of dichloride-bis(1-propylimidazole-κ1N)zinc(II), C12H20Cl2N4Zn
- Crystal structure of (E)-resveratrol 3-O-β-D-xylopyranoside, C19H22O8
- Crystal structure of 3,3′-(1,2-phenylene-bis(methylene))bis(1-vinyl- 1H-imidazol-3-ium) bis(hexafluoro phosphate)(V), C18H20F12N4P2
- Crystal structure of diaqua[bis(benzimidazol-2-yl-methyl)amine-κ3N,N′,N″]-phthalato-κ1O-nickel(II)-methanol (1/2), C26H31N5NiO8
- Crystal structure of 6,7-difluoro-1-methyl-3-(trifluoromethyl)quinoxalin-2(1H)-one, C10H5F5N2O
- Crystal structure of dichlorido-bis(1-hexyl-1H-benzotriazole-k1N)zinc(II), C24H34N6Cl2Zn
- The crystal structre of 2-(4-bromophenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine, C16H12BBrN2
- Crystal structure of diethyl 3,9-bis(4-fluorophenyl)-6,12-diphenyl-3,9-diazapentacyclo[6.4.0.02,7.04,11]dodecane-1,5-dicarboxylate, C40H36F2N2O4
- Crystal structure of (E)-7-methoxy-2-((5-methoxypyridin-3-yl)methylene)-3,4- dihydronaphthalen-1(2H)-one, C18H17NO3
- Crystal structure of (E)-2-chloro-6-(((1,3-dihydroxy-2-(oxidomethyl)propan-2-yl)imino)methyl)phenolate-κ3N,O,O’)manganese(IV), C22H24Cl2MnN2O8
- The crystal structure of α-(meta-methoxyphenoxy)-ortho-tolylic acid, C15H14O4
- The crystal structure of N-(2-chloroethyl)-N,N-diethylammonium chloride, C6H15Cl2N
- The crystal structure of tris(2,3,4,6,7,8,9,10-octahydro-1H-pyrimido[1,2-a]azepin-5-ium) trihydrodecavanadate(V), C27H54N6O28V10
- Crystal structure of 1,3-bis(octyl)benzimidazolium perchlorate C23H39ClN2O4
- Crystal structure of tetrakis[(Z)-(2-(1-(furan-2-yl)-2-methylpropylidene)-1-phenylhydrazin-1-ido-κ2N,N′)] zirconium(IV), C56H60N8O4Zr
- The crystal structure of 2-(naphthalen-2-yloxy)-4-phenyl-6-(prop-2-yn-1-yloxy)-1,3,5-triazine, C22H15N3O2
- The crystal structure of trimethylsulfonium tris(trifluoromethylsulfonyl)methanide, C7H9F9O6S4
- Crystal structure of 4-bromo-N′-[3,5-dichloro-2-hydroxyphenyl)methylidene]benzohydrazide methanol solvate, C15H13BrCl2N2O3
- The crystal structure of 4-(4-bromophenyl)-2-(3-(4-bromophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazole, C24H16Br2FN3S
- The crystal structure of N-(adamantan-1-yl)-piperidine-1-carbothioamide, C16H26N2S
- The crystal structure of 1-phenyl-N-(4,5,6,7-tetrabromo-1,3-dioxoisoindolin-2-yl)-5-(thiophen-2-yl)-1H-pyrazole-3-carboxamide-dimethylformamide (1/1) C22H10Br4N4O3S
- The crystal structure of benzeneseleninic acid anhydride, C12H10O3Se2
- The crystal structure of diphenyalmine hydrochloride antimony trichloride co-crystallizate, C12H12Cl4NSb – Localization of hydrogen atoms
- The crystal structure of para-nitrobenzylbromide, C7H6BrNO2 – A second polymorph and correction of 3D coordinates
- Crystal structure of catena-poly[(5H-pyrrolo[3,2-b:4,5-b′]dipyridine-κ2N,N′)-(μ4-hexaoxidodivanadato)dizinc(II)],C10H9N3O6V2Zn
- Crystal structure of N,N′-(2-hydroxypropane-1,3-diyl)bis(pyridine-2-aldimine)-κ5N,N′,N′′,N′′′,O]-tris(nitrato-κ2O,O′) cerium(III), C15H16CeN7O10
- Synthesis and crystal structure of oktakis(dimethylsulphoxide-κ1O)gadolinium(III) [tetrabromido-μ2-bromido-μ2-sulfido-di-μ3-sulfido-μ4-sulfido-tetracopper(I)-tungsten(VI)], C16H48O8S12Br5Cu4GdW
- Crystal structure of {tris((1H-benzo[d]imidazol-2- yl)methyl)amine-κ4N,N′,N′′,N′′′}-(succinato-κ2O,O′)nickel(II) – methanol (1/4), C32H41N7NiO8
- Crystal structure of catena-poly[trans-tetraaqua(μ2-1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol)-k2N:N′)cobalt(II)] dinitrate – 1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol) – water (1/3/2), C72H68CoN18O12
- Crystal structure of bis(μ2-2-oxido-2-phenylacetate-κ3O:O,O′)-bis(1-isopropoxy-2-oxo-2-phenylethan-1-olato-κ2O,O′)-bis(propan-2-olato-κ1O)dititanium(IV), C44H52O14Ti2
- The crystal structure of 5-carboxy-2-(hydroxymethyl)-1H-imidazol-3-ium-4-carboxylate, C6H8N2O6
- The crystal structure of 2,6-dibromo-4-fluoroaniline, C6H4Br2FN
- The crystal structure of 4-chloro-N-(2-phenoxyphenyl)benzamide, C19H14ClNO2
- The crystal structure of 2-methyl-β-naphthothiazole, C12H9NS
Artikel in diesem Heft
- Frontmatter
- New Crystal Structures
- The crystal structure of 4-hydroxybenzene-1,3-diaminium dichloride, C6H10Cl2N2O
- The crystal structure of 3-chloropropylammonium chloride, C3H9Cl2N
- The crystal structure of 1-chloro-2-(dimethylamino)ethane hydrochloride, C4H11Cl2N
- Crystal structure of N-(2-(trifluoromethyl)phenyl)hexanamide, C13H16F3NO
- Redetermination of the crystal structure of para-toluidine, C7H9N
- The crystal structure of bis(1,3-dihydroxy-2-methylpropan-2-aminium) carbonate, C9H24N2O7
- The crystal structure of 4-chloro-1-methylpiperidin-1-ium chloride, C6H13Cl2N
- Crystal structure of (Z)-3-(6-bromo-1H-indol-3-yl)-1,3-diphenylprop-2-en-1-one, C23H16BrNO
- The crystal structure of ethyl 2-amino-4-(3,5-difluorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C20H21F2NO4
- Crystal structure of 6,6'‐((1E,1'E)‐(propane‐1,3‐diylbis(azaneylylidene))bis(methaneylylidene))bis(3‐bromophenol), C34H32Br4N4O4
- The crystal structure of (E)-2-(2-((2-picolinoylhydrazono)methyl)phenoxy)acetic acid dihydrate, C15H17N3O6
- Crystal structure of (E)-4-bromo-N′-(3-chloro-2-hydroxybenzylidene)benzohydrazide, C14H10BrClN2O2
- Crystal structure of N,N′-bis(4-bromosalicylidene) ethylene-1,2-diaminopropan, C34H32Br4N4O4
- Crystal structure of 4-bromo-N′-[(3-bromo-2-hydroxyphenyl)methylidene]benzohydrazide methanol solvate, C15H14Br2N2O3
- The crystal structure of 1,2-bis(1H-benzo[d]imidazol-2-yl)ethane-1,2-diol — N-(2-aminophenyl)-3-(1H-benzo[d]imidazol-2-yl)-2,3-dihydroxypropanamide (1/1), C32H30N8O5
- The crystal structure of para-trifluoromethyl-aniline hemihydrate, C14H14F6N2O
- Redetermination of the crystal structure of 2-amino-2-methyl-propane-1,3-diole, C4H11NO2
- The crystal structure of methacholine chloride, C8H18ClNO2
- Crystal structure of 5,7,7-trimethyl-4,6,7,8-tetrahydrocyclopenta[g]isochromen-1(3H)-one, C15H18O2
- Crystal structure of poly[diammine-bis(μ4-4-hydroxypyridine-3-sulfonato-κ5N:O, O′:O′′:O′′)(μ2-pyrazinyl-κ2N:N′)tetrasilver(I)], C7H8Ag2N3O4S
- Crystal structure of ethyl (E)-5-(((3′,6′-bis(ethylamino)-3-oxospiro[isoindoline-1,9′-xanthen]-2-yl)imino)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylate — ethanol (1/1), C38H45N5O5
- Crystal structure of 4-bromo-N′-[(3-chloro-2-hydroxyphenyl)methylidene]benzohydrazide, C14H7Br2N2O2
- Redetermination of the crystal structure of 3,3,3-triphenylpropanoic acid, C21H18O2 – Deposition of hydrogen atomic coordinates
- Structure redetermination of dextromethorphan hydrobromide monohydrate, C18H28BrNO2 – localization of hydrogen atoms
- Crystal structure of tris(azido-κ1N)-(N-(2-aminoethyl)-N-methyl-1,3-propanediamine-κ3N,N′,N′′)cobalt(III), C7H19CoN12
- Crystal structure of tetraaqua-bis(1H-indazole-6-carboxylate-κN)cadmium (II), C16H18CdN4O8
- Crystal structure of dichloride-bis(1-propylimidazole-κ1N)zinc(II), C12H20Cl2N4Zn
- Crystal structure of (E)-resveratrol 3-O-β-D-xylopyranoside, C19H22O8
- Crystal structure of 3,3′-(1,2-phenylene-bis(methylene))bis(1-vinyl- 1H-imidazol-3-ium) bis(hexafluoro phosphate)(V), C18H20F12N4P2
- Crystal structure of diaqua[bis(benzimidazol-2-yl-methyl)amine-κ3N,N′,N″]-phthalato-κ1O-nickel(II)-methanol (1/2), C26H31N5NiO8
- Crystal structure of 6,7-difluoro-1-methyl-3-(trifluoromethyl)quinoxalin-2(1H)-one, C10H5F5N2O
- Crystal structure of dichlorido-bis(1-hexyl-1H-benzotriazole-k1N)zinc(II), C24H34N6Cl2Zn
- The crystal structre of 2-(4-bromophenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine, C16H12BBrN2
- Crystal structure of diethyl 3,9-bis(4-fluorophenyl)-6,12-diphenyl-3,9-diazapentacyclo[6.4.0.02,7.04,11]dodecane-1,5-dicarboxylate, C40H36F2N2O4
- Crystal structure of (E)-7-methoxy-2-((5-methoxypyridin-3-yl)methylene)-3,4- dihydronaphthalen-1(2H)-one, C18H17NO3
- Crystal structure of (E)-2-chloro-6-(((1,3-dihydroxy-2-(oxidomethyl)propan-2-yl)imino)methyl)phenolate-κ3N,O,O’)manganese(IV), C22H24Cl2MnN2O8
- The crystal structure of α-(meta-methoxyphenoxy)-ortho-tolylic acid, C15H14O4
- The crystal structure of N-(2-chloroethyl)-N,N-diethylammonium chloride, C6H15Cl2N
- The crystal structure of tris(2,3,4,6,7,8,9,10-octahydro-1H-pyrimido[1,2-a]azepin-5-ium) trihydrodecavanadate(V), C27H54N6O28V10
- Crystal structure of 1,3-bis(octyl)benzimidazolium perchlorate C23H39ClN2O4
- Crystal structure of tetrakis[(Z)-(2-(1-(furan-2-yl)-2-methylpropylidene)-1-phenylhydrazin-1-ido-κ2N,N′)] zirconium(IV), C56H60N8O4Zr
- The crystal structure of 2-(naphthalen-2-yloxy)-4-phenyl-6-(prop-2-yn-1-yloxy)-1,3,5-triazine, C22H15N3O2
- The crystal structure of trimethylsulfonium tris(trifluoromethylsulfonyl)methanide, C7H9F9O6S4
- Crystal structure of 4-bromo-N′-[3,5-dichloro-2-hydroxyphenyl)methylidene]benzohydrazide methanol solvate, C15H13BrCl2N2O3
- The crystal structure of 4-(4-bromophenyl)-2-(3-(4-bromophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazole, C24H16Br2FN3S
- The crystal structure of N-(adamantan-1-yl)-piperidine-1-carbothioamide, C16H26N2S
- The crystal structure of 1-phenyl-N-(4,5,6,7-tetrabromo-1,3-dioxoisoindolin-2-yl)-5-(thiophen-2-yl)-1H-pyrazole-3-carboxamide-dimethylformamide (1/1) C22H10Br4N4O3S
- The crystal structure of benzeneseleninic acid anhydride, C12H10O3Se2
- The crystal structure of diphenyalmine hydrochloride antimony trichloride co-crystallizate, C12H12Cl4NSb – Localization of hydrogen atoms
- The crystal structure of para-nitrobenzylbromide, C7H6BrNO2 – A second polymorph and correction of 3D coordinates
- Crystal structure of catena-poly[(5H-pyrrolo[3,2-b:4,5-b′]dipyridine-κ2N,N′)-(μ4-hexaoxidodivanadato)dizinc(II)],C10H9N3O6V2Zn
- Crystal structure of N,N′-(2-hydroxypropane-1,3-diyl)bis(pyridine-2-aldimine)-κ5N,N′,N′′,N′′′,O]-tris(nitrato-κ2O,O′) cerium(III), C15H16CeN7O10
- Synthesis and crystal structure of oktakis(dimethylsulphoxide-κ1O)gadolinium(III) [tetrabromido-μ2-bromido-μ2-sulfido-di-μ3-sulfido-μ4-sulfido-tetracopper(I)-tungsten(VI)], C16H48O8S12Br5Cu4GdW
- Crystal structure of {tris((1H-benzo[d]imidazol-2- yl)methyl)amine-κ4N,N′,N′′,N′′′}-(succinato-κ2O,O′)nickel(II) – methanol (1/4), C32H41N7NiO8
- Crystal structure of catena-poly[trans-tetraaqua(μ2-1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol)-k2N:N′)cobalt(II)] dinitrate – 1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol) – water (1/3/2), C72H68CoN18O12
- Crystal structure of bis(μ2-2-oxido-2-phenylacetate-κ3O:O,O′)-bis(1-isopropoxy-2-oxo-2-phenylethan-1-olato-κ2O,O′)-bis(propan-2-olato-κ1O)dititanium(IV), C44H52O14Ti2
- The crystal structure of 5-carboxy-2-(hydroxymethyl)-1H-imidazol-3-ium-4-carboxylate, C6H8N2O6
- The crystal structure of 2,6-dibromo-4-fluoroaniline, C6H4Br2FN
- The crystal structure of 4-chloro-N-(2-phenoxyphenyl)benzamide, C19H14ClNO2
- The crystal structure of 2-methyl-β-naphthothiazole, C12H9NS