The crystal structure of the title compound, C4H14N22+·2I-, exhibits ionic layers separated by hydrocarbon layers. The hydrocarbon layers stack in a herring-bone fashion and hydrogen bond to the iodide ions. The cation sits on a centre of inversion. The structure is compared with that of the related material butane-1,4-diammonium dichloride.
Supporting information
CCDC reference: 608416
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.019
- wR factor = 0.048
- Data-to-parameter ratio = 24.5
checkCIF/PLATON results
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Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; 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) and DIAMOND (Brandenburg,
1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).
Butane-1,4-diammonium diiodide
top
Crystal data top
C4H14N22+·2I− | F(000) = 316 |
Mr = 343.97 | Dx = 2.211 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 857 reflections |
a = 4.8983 (8) Å | θ = 2.9–28.2° |
b = 8.8210 (14) Å | µ = 6.02 mm−1 |
c = 11.981 (2) Å | T = 293 K |
β = 93.711 (3)° | Block, colourless |
V = 516.61 (15) Å3 | 0.24 × 0.18 × 0.18 mm |
Z = 2 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 890 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.054 |
Absorption correction: integration (XPREP; Bruker, 1999) | θmax = 25.5°, θmin = 2.9° |
Tmin = 0.262, Tmax = 0.455 | h = −5→5 |
4077 measured reflections | k = −10→10 |
954 independent reflections | l = −14→14 |
Refinement top
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0253P)2 + 0.1016P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.019 | (Δ/σ)max = 0.001 |
wR(F2) = 0.048 | Δρmax = 0.60 e Å−3 |
S = 1.05 | Δρmin = −0.59 e Å−3 |
954 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
39 parameters | Extinction coefficient: 0.096 (3) |
0 restraints | |
Special details top
Experimental. Numerical integration absorption corrections based on indexed crystal faces were
applied using the XPREP routine (Bruker, 1999) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.8959 (5) | 0.8113 (3) | 0.1149 (2) | 0.0461 (5) | |
H1A | 0.7745 | 0.8451 | 0.0623 | 0.069* | |
H1B | 0.999 | 0.8881 | 0.1412 | 0.069* | |
H1C | 0.8085 | 0.7705 | 0.1704 | 0.069* | |
C1 | 1.0728 (6) | 0.6946 (3) | 0.0663 (2) | 0.0417 (6) | |
H1D | 1.2137 | 0.6635 | 0.1222 | 0.05* | |
H1E | 1.1621 | 0.7381 | 0.0039 | 0.05* | |
C2 | 0.9085 (6) | 0.5577 (3) | 0.0266 (2) | 0.0408 (6) | |
H2A | 0.7636 | 0.589 | −0.0275 | 0.049* | |
H2B | 0.8247 | 0.5116 | 0.0895 | 0.049* | |
I1 | 0.59796 (4) | 0.60023 (2) | 0.335394 (13) | 0.04429 (15) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0579 (15) | 0.0353 (12) | 0.0459 (12) | −0.0046 (11) | 0.0096 (10) | −0.0031 (11) |
C1 | 0.0454 (15) | 0.0394 (14) | 0.0405 (13) | 0.0011 (12) | 0.0036 (11) | −0.0049 (12) |
C2 | 0.0426 (14) | 0.0388 (13) | 0.0413 (14) | −0.0016 (13) | 0.0059 (11) | −0.0009 (12) |
I1 | 0.05078 (19) | 0.04570 (19) | 0.03656 (17) | −0.00203 (7) | 0.00415 (9) | 0.00546 (6) |
Geometric parameters (Å, º) top
N1—C1 | 1.488 (3) | C1—H1D | 0.97 |
N1—H1A | 0.89 | C1—H1E | 0.97 |
N1—H1B | 0.89 | C2—C2i | 1.524 (5) |
N1—H1C | 0.89 | C2—H2A | 0.97 |
C1—C2 | 1.511 (4) | C2—H2B | 0.97 |
| | | |
C1—N1—H1A | 109.5 | N1—C1—H1E | 109.4 |
C1—N1—H1B | 109.5 | C2—C1—H1E | 109.4 |
H1A—N1—H1B | 109.5 | H1D—C1—H1E | 108 |
C1—N1—H1C | 109.5 | C1—C2—C2i | 110.5 (3) |
H1A—N1—H1C | 109.5 | C1—C2—H2A | 109.6 |
H1B—N1—H1C | 109.5 | C2i—C2—H2A | 109.6 |
N1—C1—C2 | 111.4 (2) | C1—C2—H2B | 109.6 |
N1—C1—H1D | 109.4 | C2i—C2—H2B | 109.6 |
C2—C1—H1D | 109.4 | H2A—C2—H2B | 108.1 |
| | | |
N1—C1—C2—C2i | 177.9 (3) | | |
Symmetry code: (i) −x+2, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···I1ii | 0.89 | 2.84 | 3.650 (3) | 152 |
N1—H1B···I1iii | 0.89 | 2.72 | 3.578 (2) | 162 |
N1—H1C···I1 | 0.89 | 2.74 | 3.616 (3) | 170 |
Symmetry codes: (ii) x, −y+3/2, z−1/2; (iii) −x+2, y+1/2, −z+1/2. |