Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801015872/cf6109sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801015872/cf6109Isup2.hkl |
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).
Fig. 1. View of asymmetric unit of (I) (70% probability displacement ellipsoids) | |
Fig. 2. Unit-cell packing diagram of (I) viewed along the b axis. |
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 |
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 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) |
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 |
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 |
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 |
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. |
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) |
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) |
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) |
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) |
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).
C1—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) |
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. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
NO COMMENT