The dication and chloride ions of (1
R,2
R)-1,2-diammoniocyclohexane dichloride, C
6H
16N
22+·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
CCDC reference: 175991
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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.
The title compound was recrystallized from ethanol. It is the serendipitous
hydrolysis product of a diimine ligand, for which it is also the precursor.
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).
(1
R,2
R)-1,2-diammoniocyclohexane dichloride
top
Crystal data top
C6H16N22+·2Cl− | F(000) = 400 |
Mr = 187.11 | Dx = 1.341 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1549 reflections |
a = 8.1138 (2) Å | θ = 1–30.0° |
b = 9.5567 (2) Å | µ = 0.64 mm−1 |
c = 11.9553 (3) Å | T = 150 K |
V = 927.03 (4) Å3 | Prism, colourless |
Z = 4 | 0.5 × 0.4 × 0.35 mm |
Data collection top
KappaCCD diffractometer | 2709 independent reflections |
Radiation source: Enraf Nonius FR590 | 2662 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
CCD rotation images, thick slices scans | θmax = 30.0°, θmin = 2.7° |
Absorption correction: multi-scan (Blessing, 1995) | h = −11→11 |
Tmin = 0.751, Tmax = 0.800 | k = −13→13 |
10435 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.017 | All 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 reflections | Δρmax = 0.26 e Å−3 |
155 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Absolute structure: Flack (1983); 1131 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.07 (4) |
Crystal data top
C6H16N22+·2Cl− | V = 927.03 (4) Å3 |
Mr = 187.11 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.1138 (2) Å | µ = 0.64 mm−1 |
b = 9.5567 (2) Å | T = 150 K |
c = 11.9553 (3) Å | 0.5 × 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 = 0.800 | Rint = 0.024 |
10435 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.017 | All H-atom parameters refined |
wR(F2) = 0.047 | Δρmax = 0.26 e Å−3 |
S = 1.06 | Δρmin = −0.15 e Å−3 |
2709 reflections | Absolute structure: Flack (1983); 1131 Friedel pairs |
155 parameters | Absolute 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.84126 (11) | 0.68318 (9) | 0.81150 (7) | 0.01344 (16) | |
C2 | 0.77962 (10) | 0.78883 (9) | 0.72548 (7) | 0.01270 (15) | |
C3 | 0.87040 (11) | 0.77177 (10) | 0.61396 (8) | 0.01593 (16) | |
C4 | 1.05655 (13) | 0.78302 (10) | 0.62952 (8) | 0.01958 (17) | |
C5 | 1.11555 (12) | 0.67302 (11) | 0.71228 (9) | 0.02073 (19) | |
C6 | 1.02859 (12) | 0.69127 (11) | 0.82438 (8) | 0.01883 (18) | |
N1 | 0.76452 (10) | 0.70698 (9) | 0.92416 (7) | 0.01709 (15) | |
N2 | 0.59826 (10) | 0.77390 (9) | 0.70477 (7) | 0.01484 (15) | |
H1 | 0.8095 (14) | 0.5891 (12) | 0.7908 (10) | 0.014 (3)* | |
H1A | 0.7783 (18) | 0.7989 (15) | 0.9464 (12) | 0.025 (3)* | |
H1B | 0.8164 (18) | 0.6539 (16) | 0.9781 (12) | 0.028 (4)* | |
H1C | 0.6564 (18) | 0.6844 (15) | 0.9241 (12) | 0.027 (3)* | |
H2 | 0.7922 (13) | 0.8850 (11) | 0.7557 (9) | 0.008 (3)* | |
H2A | 0.579 (2) | 0.6885 (17) | 0.6809 (12) | 0.032 (4)* | |
H2B | 0.5729 (17) | 0.8354 (15) | 0.6498 (11) | 0.023 (3)* | |
H2C | 0.5437 (19) | 0.7963 (15) | 0.7661 (13) | 0.035 (4)* | |
H3A | 0.8422 (16) | 0.6787 (14) | 0.5828 (11) | 0.020 (3)* | |
H3B | 0.8294 (15) | 0.8464 (14) | 0.5631 (12) | 0.020 (3)* | |
H4A | 1.1092 (18) | 0.7700 (15) | 0.5558 (13) | 0.028 (4)* | |
H4B | 1.0852 (17) | 0.8793 (15) | 0.6585 (11) | 0.025 (3)* | |
H5A | 1.228 (2) | 0.6814 (16) | 0.7249 (13) | 0.033 (4)* | |
H5B | 1.0922 (17) | 0.5796 (15) | 0.6816 (11) | 0.025 (3)* | |
H6A | 1.0523 (18) | 0.7840 (15) | 0.8592 (11) | 0.025 (3)* | |
H6B | 1.0636 (17) | 0.6201 (15) | 0.8791 (11) | 0.026 (3)* | |
Cl1 | 0.44987 (3) | 0.96509 (2) | 0.890027 (18) | 0.02277 (6) | |
Cl2 | 0.43518 (3) | 0.54545 (2) | 0.939872 (19) | 0.02099 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0148 (4) | 0.0138 (4) | 0.0117 (4) | 0.0002 (3) | −0.0007 (3) | 0.0001 (3) |
C2 | 0.0128 (4) | 0.0112 (3) | 0.0141 (4) | 0.0000 (3) | −0.0008 (3) | 0.0007 (3) |
C3 | 0.0170 (4) | 0.0178 (4) | 0.0130 (4) | 0.0026 (3) | 0.0011 (3) | 0.0020 (3) |
C4 | 0.0174 (4) | 0.0217 (4) | 0.0196 (4) | 0.0009 (4) | 0.0043 (4) | 0.0029 (3) |
C5 | 0.0152 (4) | 0.0264 (5) | 0.0206 (4) | 0.0055 (4) | 0.0014 (3) | 0.0024 (4) |
C6 | 0.0151 (4) | 0.0241 (5) | 0.0172 (4) | 0.0015 (3) | −0.0020 (3) | 0.0022 (3) |
N1 | 0.0162 (4) | 0.0214 (4) | 0.0137 (3) | −0.0026 (3) | 0.0004 (3) | 0.0009 (3) |
N2 | 0.0141 (3) | 0.0143 (3) | 0.0162 (3) | 0.0015 (3) | −0.0012 (3) | −0.0007 (3) |
Cl1 | 0.03460 (13) | 0.01573 (9) | 0.01798 (10) | 0.00634 (10) | 0.00850 (9) | 0.00304 (8) |
Cl2 | 0.01902 (10) | 0.01764 (10) | 0.02631 (11) | −0.00391 (9) | 0.00147 (8) | −0.00677 (8) |
Geometric parameters (Å, º) top
C1—N1 | 1.5012 (12) | C4—H4B | 1.010 (14) |
C1—C2 | 1.5254 (12) | C5—C6 | 1.5246 (14) |
C1—C6 | 1.5296 (12) | C5—H5A | 0.927 (17) |
C1—H1 | 0.968 (12) | C5—H5B | 0.984 (14) |
C2—N2 | 1.4990 (11) | C6—H6A | 0.998 (14) |
C2—C3 | 1.5319 (13) | C6—H6B | 0.985 (14) |
C2—H2 | 0.993 (11) | N1—H1A | 0.924 (15) |
C3—C4 | 1.5256 (14) | N1—H1B | 0.922 (15) |
C3—H3A | 0.991 (14) | N1—H1C | 0.903 (15) |
C3—H3B | 0.995 (13) | N2—H2A | 0.878 (16) |
C4—C5 | 1.5209 (14) | N2—H2B | 0.905 (14) |
C4—H4A | 0.988 (15) | N2—H2C | 0.883 (17) |
| | | |
N1—C1—C2 | 111.63 (7) | C4—C5—C6 | 110.31 (8) |
N1—C1—C6 | 108.31 (7) | C4—C5—H5A | 110.8 (10) |
C2—C1—C6 | 111.12 (8) | C6—C5—H5A | 107.6 (10) |
N1—C1—H1 | 105.1 (7) | C4—C5—H5B | 108.9 (8) |
C2—C1—H1 | 110.8 (7) | C6—C5—H5B | 110.0 (8) |
C6—C1—H1 | 109.7 (7) | H5A—C5—H5B | 109.2 (12) |
N2—C2—C1 | 111.73 (7) | C5—C6—C1 | 111.44 (8) |
N2—C2—C3 | 108.55 (7) | C5—C6—H6A | 112.3 (8) |
C1—C2—C3 | 111.02 (7) | C1—C6—H6A | 106.2 (8) |
N2—C2—H2 | 104.4 (6) | C5—C6—H6B | 111.8 (8) |
C1—C2—H2 | 109.5 (6) | C1—C6—H6B | 108.6 (8) |
C3—C2—H2 | 111.5 (6) | H6A—C6—H6B | 106.3 (11) |
C4—C3—C2 | 111.25 (8) | C1—N1—H1A | 110.6 (9) |
C4—C3—H3A | 109.7 (8) | C1—N1—H1B | 110.8 (9) |
C2—C3—H3A | 108.1 (8) | H1A—N1—H1B | 105.4 (13) |
C4—C3—H3B | 110.8 (7) | C1—N1—H1C | 111.5 (9) |
C2—C3—H3B | 107.1 (8) | H1A—N1—H1C | 110.2 (13) |
H3A—C3—H3B | 109.7 (11) | H1B—N1—H1C | 108.2 (13) |
C5—C4—C3 | 110.02 (8) | C2—N2—H2A | 108.4 (11) |
C5—C4—H4A | 111.0 (9) | C2—N2—H2B | 106.3 (9) |
C3—C4—H4A | 108.1 (9) | H2A—N2—H2B | 109.1 (13) |
C5—C4—H4B | 109.5 (8) | C2—N2—H2C | 109.4 (10) |
C3—C4—H4B | 109.5 (8) | H2A—N2—H2C | 114.0 (14) |
H4A—C4—H4B | 108.8 (11) | H2B—N2—H2C | 109.3 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Cl2i | 0.924 (15) | 2.384 (15) | 3.1871 (9) | 145.2 (12) |
N1—H1B···Cl1i | 0.922 (15) | 2.225 (15) | 3.1466 (9) | 177.1 (13) |
N1—H1C···Cl2 | 0.903 (15) | 2.241 (15) | 3.0918 (9) | 156.9 (12) |
N2—H2A···Cl1ii | 0.878 (16) | 2.309 (16) | 3.1853 (8) | 175.1 (15) |
N2—H2B···Cl2iii | 0.905 (14) | 2.277 (14) | 3.1303 (9) | 157.1 (12) |
N2—H2C···Cl1 | 0.883 (17) | 2.319 (16) | 3.1134 (8) | 149.8 (13) |
Symmetry codes: (i) x+1/2, −y+3/2, −z+2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, y+1/2, −z+3/2. |
Experimental details
Crystal data |
Chemical formula | C6H16N22+·2Cl− |
Mr | 187.11 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 150 |
a, b, c (Å) | 8.1138 (2), 9.5567 (2), 11.9553 (3) |
V (Å3) | 927.03 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.64 |
Crystal size (mm) | 0.5 × 0.4 × 0.35 |
|
Data collection |
Diffractometer | KappaCCD diffractometer |
Absorption correction | Multi-scan (Blessing, 1995) |
Tmin, Tmax | 0.751, 0.800 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10435, 2709, 2662 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.704 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.017, 0.047, 1.06 |
No. of reflections | 2709 |
No. of parameters | 155 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.26, −0.15 |
Absolute structure | Flack (1983); 1131 Friedel pairs |
Absolute structure parameter | −0.07 (4) |
Selected geometric parameters (Å, º) topC1—N1 | 1.5012 (12) | C2—C3 | 1.5319 (13) |
C1—C2 | 1.5254 (12) | C3—C4 | 1.5256 (14) |
C1—C6 | 1.5296 (12) | C4—C5 | 1.5209 (14) |
C2—N2 | 1.4990 (11) | C5—C6 | 1.5246 (14) |
| | | |
N1—C1—C2 | 111.63 (7) | C1—C2—C3 | 111.02 (7) |
N1—C1—C6 | 108.31 (7) | C4—C3—C2 | 111.25 (8) |
C2—C1—C6 | 111.12 (8) | C5—C4—C3 | 110.02 (8) |
N2—C2—C1 | 111.73 (7) | C4—C5—C6 | 110.31 (8) |
N2—C2—C3 | 108.55 (7) | C5—C6—C1 | 111.44 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Cl2i | 0.924 (15) | 2.384 (15) | 3.1871 (9) | 145.2 (12) |
N1—H1B···Cl1i | 0.922 (15) | 2.225 (15) | 3.1466 (9) | 177.1 (13) |
N1—H1C···Cl2 | 0.903 (15) | 2.241 (15) | 3.0918 (9) | 156.9 (12) |
N2—H2A···Cl1ii | 0.878 (16) | 2.309 (16) | 3.1853 (8) | 175.1 (15) |
N2—H2B···Cl2iii | 0.905 (14) | 2.277 (14) | 3.1303 (9) | 157.1 (12) |
N2—H2C···Cl1 | 0.883 (17) | 2.319 (16) | 3.1134 (8) | 149.8 (13) |
Symmetry codes: (i) x+1/2, −y+3/2, −z+2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, y+1/2, −z+3/2. |
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