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The anion and the cation of the title compound, C
6H
16N
+·I
−, are located on special positions of site symmetry 3
m. As a result, there is only a sixth of an ion pair in the asymmetric unit. The anion and cation are connected
via an N—H
I hydrogen bond. Each methylene group is disordered over two equally occupied positions.
Supporting information
CCDC reference: 239283
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (Please check) = 0.000 Å
- R factor = 0.025
- wR factor = 0.071
- Data-to-parameter ratio = 18.6
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT301_ALERT_3_B Main Residue Disorder ......................... 27.00 Perc.
Alert level C
STRVA01_ALERT_4_C Flack test results are ambiguous.
From the CIF: _refine_ls_abs_structure_Flack 0.500
From the CIF: _refine_ls_abs_structure_Flack_su 0.130
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.50
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.31
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C1
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.14 Ratio
Alert level G
REFLT03_ALERT_4_G 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.
From the CIF: _diffrn_reflns_theta_max 27.54
From the CIF: _reflns_number_total 464
Count of symmetry unique reflns 254
Completeness (_total/calc) 182.68%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 210
Fraction of Friedel pairs measured 0.827
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 1990).
Crystal data top
C6H16N+·I− | Dx = 1.497 Mg m−3 |
Mr = 229.10 | Mo Kα radiation, λ = 0.71073 Å |
Hexagonal, P63mc | Cell parameters from 12855 reflections |
Hall symbol: P 6c -2c | θ = 3.8–27.5° |
a = 8.6555 (11) Å | µ = 3.08 mm−1 |
c = 7.8351 (9) Å | T = 173 K |
V = 508.35 (11) Å3 | Needle, colourless |
Z = 2 | 0.35 × 0.12 × 0.11 mm |
F(000) = 224 | |
Data collection top
Stoe IPDS-II two-circle diffractometer | 464 independent reflections |
Radiation source: fine-focus sealed tube | 421 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ω scans | θmax = 27.5°, θmin = 4.7° |
Absorption correction: multi-scan (MULABS; Spek, 1990; Blessing, 1995) | h = −11→11 |
Tmin = 0.404, Tmax = 0.714 | k = −11→11 |
5945 measured reflections | l = −10→10 |
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)] = 0.025 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.071 | w = 1/[σ2(Fo2) + (0.0533P)2 + 0.0681P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
464 reflections | Δρmax = 1.00 e Å−3 |
25 parameters | Δρmin = −0.43 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 232 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.50 (13) |
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 | Occ. (<1) |
I1 | 0.6667 | 0.3333 | 0.3706 | 0.0532 (2) | |
N1 | 0.6667 | 0.3333 | 0.8210 (14) | 0.053 (2) | |
H1 | 0.6667 | 0.3333 | 0.70 (3) | 0.07 (5)* | |
C1 | 0.6898 (10) | 0.1799 (11) | 0.8459 (12) | 0.047 (2) | 0.50 |
H1A | 0.6766 | 0.1219 | 0.7340 | 0.056* | 0.50 |
H1B | 0.5813 | 0.0987 | 0.9111 | 0.056* | 0.50 |
C2 | 0.8335 (5) | 0.1665 (5) | 0.9478 (13) | 0.0740 (19) | |
H2A | 0.8038 | 0.0419 | 0.9509 | 0.111* | 0.25 |
H2B | 0.9446 | 0.2387 | 0.8879 | 0.111* | 0.25 |
H2C | 0.8430 | 0.2104 | 1.0654 | 0.111* | 0.25 |
H2D | 0.9564 | 0.1945 | 0.9509 | 0.111* | 0.25 |
H2E | 0.7879 | 0.1553 | 1.0654 | 0.111* | 0.25 |
H2F | 0.7596 | 0.0538 | 0.8879 | 0.111* | 0.25 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0535 (2) | 0.0535 (2) | 0.0525 (3) | 0.02675 (11) | 0.000 | 0.000 |
N1 | 0.043 (2) | 0.043 (2) | 0.071 (7) | 0.0217 (12) | 0.000 | 0.000 |
C1 | 0.062 (3) | 0.054 (3) | 0.027 (6) | 0.031 (2) | −0.003 (2) | 0.000 (2) |
C2 | 0.069 (3) | 0.069 (3) | 0.099 (5) | 0.045 (4) | −0.0022 (16) | 0.0022 (16) |
Geometric parameters (Å, º) top
N1—C1i | 1.452 (8) | C1—H1B | 0.9884 |
N1—C1ii | 1.452 (8) | C2—C1i | 1.530 (11) |
N1—C1iii | 1.452 (8) | C2—H2A | 0.9757 |
N1—C1 | 1.452 (8) | C2—H2B | 0.9664 |
N1—C1iv | 1.452 (8) | C2—H2C | 0.9846 |
N1—C1v | 1.452 (8) | C2—H2D | 0.9657 |
N1—H1 | 0.9 (2) | C2—H2E | 0.9882 |
C1—C2 | 1.530 (11) | C2—H2F | 0.9784 |
C1—H1A | 0.9883 | | |
| | | |
C1i—N1—C1iii | 118.2 (3) | N1—C1—H1B | 101.7 |
C1ii—N1—C1 | 118.2 (3) | C2—C1—H1B | 101.3 |
C1i—N1—C1iv | 118.2 (3) | H1A—C1—H1B | 105.7 |
C1iii—N1—C1iv | 118.2 (3) | C1—C2—H2A | 108.8 |
C1ii—N1—C1v | 118.2 (3) | C1—C2—H2B | 106.3 |
C1—N1—C1v | 118.2 (3) | H2A—C2—H2B | 110.7 |
C1i—N1—H1 | 97.7 (6) | C1—C2—H2C | 111.9 |
C1ii—N1—H1 | 97.7 (6) | H2A—C2—H2C | 109.2 |
C1iii—N1—H1 | 97.7 (6) | H2B—C2—H2C | 109.9 |
C1—N1—H1 | 97.7 (6) | C1i—C2—H2D | 109.3 |
C1iv—N1—H1 | 97.7 (5) | C1—C2—H2E | 101.2 |
C1v—N1—H1 | 97.7 (5) | H2D—C2—H2E | 109.7 |
N1—C1—C2 | 128.9 (7) | C1i—C2—H2F | 106.4 |
N1—C1—H1A | 108.1 | H2D—C2—H2F | 110.5 |
C2—C1—H1A | 108.5 | H2E—C2—H2F | 108.6 |
Symmetry codes: (i) −y+1, −x+1, z; (ii) −y+1, x−y, z; (iii) x, x−y, z; (iv) −x+y+1, y, z; (v) −x+y+1, −x+1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···I1 | 0.9 (2) | 2.6 (2) | 3.529 (11) | 180 |
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