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The dication and chloride ions of (1R,2R)-1,2-di­ammonio­cyclo­hexane dichloride, C6H16N22+·2Cl, (I), lie in general positions. The cyclo­hexane ring adopts the expected chair conformation, with equatorial ammonio substituents. The cation and chloride ions stack parallel to the b axis. All six ammonio H atoms are involved in hydrogen bonds to the chloride ions. The Cl...H contacts range from 2.225 (15) to 2.384 (15) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801015872/cf6109sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801015872/cf6109Isup2.hkl
Contains datablock I

CCDC reference: 175991

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.017
  • wR factor = 0.047
  • Data-to-parameter ratio = 17.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 30.04 From the CIF: _reflns_number_total 2709 Count of symmetry unique reflns 1581 Completeness (_total/calc) 171.35% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1128 Fraction of Friedel pairs measured 0.713 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.

Comment top

NO COMMENT

Experimental top

The title compound was recrystallized from ethanol. It is the serendipitous hydrolysis product of a diimine ligand, for which it is also the precursor.

Computing details top

Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and WinGX (Farrugia, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. View of asymmetric unit of (I) (70% probability displacement ellipsoids)
[Figure 2] Fig. 2. Unit-cell packing diagram of (I) viewed along the b axis.
(1R,2R)-1,2-diammoniocyclohexane dichloride top
Crystal data top
C6H16N22+·2ClF(000) = 400
Mr = 187.11Dx = 1.341 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1549 reflections
a = 8.1138 (2) Åθ = 1–30.0°
b = 9.5567 (2) ŵ = 0.64 mm1
c = 11.9553 (3) ÅT = 150 K
V = 927.03 (4) Å3Prism, colourless
Z = 40.5 × 0.4 × 0.35 mm
Data collection top
KappaCCD
diffractometer
2709 independent reflections
Radiation source: Enraf Nonius FR5902662 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
CCD rotation images, thick slices scansθmax = 30.0°, θmin = 2.7°
Absorption correction: multi-scan
(Blessing, 1995)
h = 1111
Tmin = 0.751, Tmax = 0.800k = 1313
10435 measured reflectionsl = 1616
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.017All H-atom parameters refined
wR(F2) = 0.047 w = 1/[σ2(Fo2) + (0.024P)2 + 0.1345P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
2709 reflectionsΔρmax = 0.26 e Å3
155 parametersΔρmin = 0.15 e Å3
0 restraintsAbsolute structure: Flack (1983); 1131 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.07 (4)
Crystal data top
C6H16N22+·2ClV = 927.03 (4) Å3
Mr = 187.11Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.1138 (2) ŵ = 0.64 mm1
b = 9.5567 (2) ÅT = 150 K
c = 11.9553 (3) Å0.5 × 0.4 × 0.35 mm
Data collection top
KappaCCD
diffractometer
2709 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
2662 reflections with I > 2σ(I)
Tmin = 0.751, Tmax = 0.800Rint = 0.024
10435 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.017All H-atom parameters refined
wR(F2) = 0.047Δρmax = 0.26 e Å3
S = 1.06Δρmin = 0.15 e Å3
2709 reflectionsAbsolute structure: Flack (1983); 1131 Friedel pairs
155 parametersAbsolute structure parameter: 0.07 (4)
0 restraints
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.84126 (11)0.68318 (9)0.81150 (7)0.01344 (16)
C20.77962 (10)0.78883 (9)0.72548 (7)0.01270 (15)
C30.87040 (11)0.77177 (10)0.61396 (8)0.01593 (16)
C41.05655 (13)0.78302 (10)0.62952 (8)0.01958 (17)
C51.11555 (12)0.67302 (11)0.71228 (9)0.02073 (19)
C61.02859 (12)0.69127 (11)0.82438 (8)0.01883 (18)
N10.76452 (10)0.70698 (9)0.92416 (7)0.01709 (15)
N20.59826 (10)0.77390 (9)0.70477 (7)0.01484 (15)
H10.8095 (14)0.5891 (12)0.7908 (10)0.014 (3)*
H1A0.7783 (18)0.7989 (15)0.9464 (12)0.025 (3)*
H1B0.8164 (18)0.6539 (16)0.9781 (12)0.028 (4)*
H1C0.6564 (18)0.6844 (15)0.9241 (12)0.027 (3)*
H20.7922 (13)0.8850 (11)0.7557 (9)0.008 (3)*
H2A0.579 (2)0.6885 (17)0.6809 (12)0.032 (4)*
H2B0.5729 (17)0.8354 (15)0.6498 (11)0.023 (3)*
H2C0.5437 (19)0.7963 (15)0.7661 (13)0.035 (4)*
H3A0.8422 (16)0.6787 (14)0.5828 (11)0.020 (3)*
H3B0.8294 (15)0.8464 (14)0.5631 (12)0.020 (3)*
H4A1.1092 (18)0.7700 (15)0.5558 (13)0.028 (4)*
H4B1.0852 (17)0.8793 (15)0.6585 (11)0.025 (3)*
H5A1.228 (2)0.6814 (16)0.7249 (13)0.033 (4)*
H5B1.0922 (17)0.5796 (15)0.6816 (11)0.025 (3)*
H6A1.0523 (18)0.7840 (15)0.8592 (11)0.025 (3)*
H6B1.0636 (17)0.6201 (15)0.8791 (11)0.026 (3)*
Cl10.44987 (3)0.96509 (2)0.890027 (18)0.02277 (6)
Cl20.43518 (3)0.54545 (2)0.939872 (19)0.02099 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0148 (4)0.0138 (4)0.0117 (4)0.0002 (3)0.0007 (3)0.0001 (3)
C20.0128 (4)0.0112 (3)0.0141 (4)0.0000 (3)0.0008 (3)0.0007 (3)
C30.0170 (4)0.0178 (4)0.0130 (4)0.0026 (3)0.0011 (3)0.0020 (3)
C40.0174 (4)0.0217 (4)0.0196 (4)0.0009 (4)0.0043 (4)0.0029 (3)
C50.0152 (4)0.0264 (5)0.0206 (4)0.0055 (4)0.0014 (3)0.0024 (4)
C60.0151 (4)0.0241 (5)0.0172 (4)0.0015 (3)0.0020 (3)0.0022 (3)
N10.0162 (4)0.0214 (4)0.0137 (3)0.0026 (3)0.0004 (3)0.0009 (3)
N20.0141 (3)0.0143 (3)0.0162 (3)0.0015 (3)0.0012 (3)0.0007 (3)
Cl10.03460 (13)0.01573 (9)0.01798 (10)0.00634 (10)0.00850 (9)0.00304 (8)
Cl20.01902 (10)0.01764 (10)0.02631 (11)0.00391 (9)0.00147 (8)0.00677 (8)
Geometric parameters (Å, º) top
C1—N11.5012 (12)C4—H4B1.010 (14)
C1—C21.5254 (12)C5—C61.5246 (14)
C1—C61.5296 (12)C5—H5A0.927 (17)
C1—H10.968 (12)C5—H5B0.984 (14)
C2—N21.4990 (11)C6—H6A0.998 (14)
C2—C31.5319 (13)C6—H6B0.985 (14)
C2—H20.993 (11)N1—H1A0.924 (15)
C3—C41.5256 (14)N1—H1B0.922 (15)
C3—H3A0.991 (14)N1—H1C0.903 (15)
C3—H3B0.995 (13)N2—H2A0.878 (16)
C4—C51.5209 (14)N2—H2B0.905 (14)
C4—H4A0.988 (15)N2—H2C0.883 (17)
N1—C1—C2111.63 (7)C4—C5—C6110.31 (8)
N1—C1—C6108.31 (7)C4—C5—H5A110.8 (10)
C2—C1—C6111.12 (8)C6—C5—H5A107.6 (10)
N1—C1—H1105.1 (7)C4—C5—H5B108.9 (8)
C2—C1—H1110.8 (7)C6—C5—H5B110.0 (8)
C6—C1—H1109.7 (7)H5A—C5—H5B109.2 (12)
N2—C2—C1111.73 (7)C5—C6—C1111.44 (8)
N2—C2—C3108.55 (7)C5—C6—H6A112.3 (8)
C1—C2—C3111.02 (7)C1—C6—H6A106.2 (8)
N2—C2—H2104.4 (6)C5—C6—H6B111.8 (8)
C1—C2—H2109.5 (6)C1—C6—H6B108.6 (8)
C3—C2—H2111.5 (6)H6A—C6—H6B106.3 (11)
C4—C3—C2111.25 (8)C1—N1—H1A110.6 (9)
C4—C3—H3A109.7 (8)C1—N1—H1B110.8 (9)
C2—C3—H3A108.1 (8)H1A—N1—H1B105.4 (13)
C4—C3—H3B110.8 (7)C1—N1—H1C111.5 (9)
C2—C3—H3B107.1 (8)H1A—N1—H1C110.2 (13)
H3A—C3—H3B109.7 (11)H1B—N1—H1C108.2 (13)
C5—C4—C3110.02 (8)C2—N2—H2A108.4 (11)
C5—C4—H4A111.0 (9)C2—N2—H2B106.3 (9)
C3—C4—H4A108.1 (9)H2A—N2—H2B109.1 (13)
C5—C4—H4B109.5 (8)C2—N2—H2C109.4 (10)
C3—C4—H4B109.5 (8)H2A—N2—H2C114.0 (14)
H4A—C4—H4B108.8 (11)H2B—N2—H2C109.3 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl2i0.924 (15)2.384 (15)3.1871 (9)145.2 (12)
N1—H1B···Cl1i0.922 (15)2.225 (15)3.1466 (9)177.1 (13)
N1—H1C···Cl20.903 (15)2.241 (15)3.0918 (9)156.9 (12)
N2—H2A···Cl1ii0.878 (16)2.309 (16)3.1853 (8)175.1 (15)
N2—H2B···Cl2iii0.905 (14)2.277 (14)3.1303 (9)157.1 (12)
N2—H2C···Cl10.883 (17)2.319 (16)3.1134 (8)149.8 (13)
Symmetry codes: (i) x+1/2, y+3/2, z+2; (ii) x+1, y1/2, z+3/2; (iii) x+1, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC6H16N22+·2Cl
Mr187.11
Crystal system, space groupOrthorhombic, P212121
Temperature (K)150
a, b, c (Å)8.1138 (2), 9.5567 (2), 11.9553 (3)
V3)927.03 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.64
Crystal size (mm)0.5 × 0.4 × 0.35
Data collection
DiffractometerKappaCCD
diffractometer
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.751, 0.800
No. of measured, independent and
observed [I > 2σ(I)] reflections
10435, 2709, 2662
Rint0.024
(sin θ/λ)max1)0.704
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.017, 0.047, 1.06
No. of reflections2709
No. of parameters155
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.26, 0.15
Absolute structureFlack (1983); 1131 Friedel pairs
Absolute structure parameter0.07 (4)

Computer programs: COLLECT (Nonius, 1997-2000), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and WinGX (Farrugia, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX publication routines (Farrugia, 1999).

Selected geometric parameters (Å, º) top
C1—N11.5012 (12)C2—C31.5319 (13)
C1—C21.5254 (12)C3—C41.5256 (14)
C1—C61.5296 (12)C4—C51.5209 (14)
C2—N21.4990 (11)C5—C61.5246 (14)
N1—C1—C2111.63 (7)C1—C2—C3111.02 (7)
N1—C1—C6108.31 (7)C4—C3—C2111.25 (8)
C2—C1—C6111.12 (8)C5—C4—C3110.02 (8)
N2—C2—C1111.73 (7)C4—C5—C6110.31 (8)
N2—C2—C3108.55 (7)C5—C6—C1111.44 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl2i0.924 (15)2.384 (15)3.1871 (9)145.2 (12)
N1—H1B···Cl1i0.922 (15)2.225 (15)3.1466 (9)177.1 (13)
N1—H1C···Cl20.903 (15)2.241 (15)3.0918 (9)156.9 (12)
N2—H2A···Cl1ii0.878 (16)2.309 (16)3.1853 (8)175.1 (15)
N2—H2B···Cl2iii0.905 (14)2.277 (14)3.1303 (9)157.1 (12)
N2—H2C···Cl10.883 (17)2.319 (16)3.1134 (8)149.8 (13)
Symmetry codes: (i) x+1/2, y+3/2, z+2; (ii) x+1, y1/2, z+3/2; (iii) x+1, y+1/2, z+3/2.
 

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