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The structure of the title compound, C14H16P+·I-, has been reported previously by Staples, Carlson, Wang & Fackler [Acta Cryst. (1995), C51, 498-500] in the space group P6522 without any information about the determination of the absolute structure. We present here a redetermination of this structure from new intensity data in the space group P6122 with the direction of the polar axis unequivocally determined for this particular crystal. Both the cation and anion are located on twofold rotation axes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805013012/sj6077sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805013012/sj6077Isup2.hkl
Contains datablock I

CCDC reference: 274629

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.020
  • wR factor = 0.047
  • Data-to-parameter ratio = 19.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.59 Ratio PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.54
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 26.28 From the CIF: _reflns_number_total 1475 Count of symmetry unique reflns 932 Completeness (_total/calc) 158.26% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 543 Fraction of Friedel pairs measured 0.583 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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, 2003).

dimethyldiphenylphosphonium iodide top
Crystal data top
C14H16P+·IDx = 1.560 Mg m3
Mr = 342.14Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P6122Cell parameters from 28706 reflections
Hall symbol: P 61 2 (0 0 -1)θ = 3.6–26.7°
a = 11.7463 (6) ŵ = 2.28 mm1
c = 18.2841 (10) ÅT = 173 K
V = 2184.8 (2) Å3Block, colourless
Z = 60.22 × 0.20 × 0.17 mm
F(000) = 1008
Data collection top
Stoe IPDS-II two-circle
diffractometer
1475 independent reflections
Radiation source: fine-focus sealed tube1445 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scansθmax = 26.3°, θmin = 3.6°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 1414
Tmin = 0.634, Tmax = 0.698k = 1414
15434 measured reflectionsl = 2218
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)] = 0.020H-atom parameters constrained
wR(F2) = 0.047 w = 1/[σ2(Fo2) + (0.0253P)2 + 0.9694P]
where P = (Fo2 + 2Fc2)/3
S = 1.20(Δ/σ)max = 0.001
1475 reflectionsΔρmax = 0.23 e Å3
74 parametersΔρmin = 0.68 e Å3
0 restraintsAbsolute structure: Flack, (1983) 546 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (3)
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
I10.00000.53561 (2)0.33330.03190 (9)
P10.57224 (4)0.42776 (4)0.41670.01702 (17)
C10.3972 (2)0.3570 (2)0.42262 (14)0.0243 (5)
C20.3231 (3)0.2622 (3)0.47462 (17)0.0429 (8)
H20.36410.23420.50940.052*
C30.1860 (4)0.2087 (4)0.4746 (2)0.0628 (12)
H30.13350.14340.50950.075*
C40.1269 (3)0.2507 (4)0.4240 (2)0.0628 (12)
H40.03420.21430.42480.075*
C50.2010 (3)0.3445 (4)0.3728 (2)0.0531 (10)
H50.15960.37260.33830.064*
C60.3363 (3)0.3979 (3)0.37155 (18)0.0353 (6)
H60.38770.46230.33600.042*
C70.6366 (3)0.3906 (2)0.49560 (14)0.0276 (5)
H7A0.61650.42580.53920.041*
H7B0.73210.43040.49070.041*
H7C0.59660.29500.50030.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02322 (12)0.03242 (11)0.03698 (13)0.01161 (6)0.01088 (10)0.00544 (5)
P10.0169 (3)0.0169 (3)0.0189 (4)0.0096 (3)0.0014 (3)0.0014 (3)
C10.0210 (11)0.0233 (11)0.0292 (12)0.0116 (9)0.0014 (10)0.0114 (9)
C20.0306 (16)0.0479 (18)0.0329 (14)0.0065 (14)0.0099 (12)0.0058 (13)
C30.0350 (18)0.070 (3)0.052 (2)0.0026 (17)0.0197 (16)0.0214 (18)
C40.0218 (14)0.084 (3)0.078 (3)0.0227 (16)0.0055 (17)0.054 (2)
C50.0327 (16)0.059 (2)0.082 (2)0.0330 (15)0.0223 (18)0.041 (2)
C60.0305 (14)0.0319 (14)0.0506 (16)0.0209 (12)0.0133 (12)0.0150 (13)
C70.0349 (13)0.0238 (12)0.0263 (12)0.0164 (11)0.0052 (12)0.0005 (11)
Geometric parameters (Å, º) top
P1—C7i1.782 (3)C3—H30.9500
P1—C71.782 (3)C4—C51.375 (6)
P1—C1i1.794 (3)C4—H40.9500
P1—C11.794 (3)C5—C61.387 (4)
C1—C21.390 (4)C5—H50.9500
C1—C61.400 (4)C6—H60.9500
C2—C31.406 (5)C7—H7A0.9800
C2—H20.9500C7—H7B0.9800
C3—C41.387 (6)C7—H7C0.9800
C7i—P1—C7109.13 (17)C5—C4—C3120.7 (3)
C7i—P1—C1i111.43 (12)C5—C4—H4119.7
C7—P1—C1i108.63 (11)C3—C4—H4119.7
C7i—P1—C1108.63 (11)C4—C5—C6119.8 (3)
C7—P1—C1111.43 (12)C4—C5—H5120.1
C1i—P1—C1107.59 (15)C6—C5—H5120.1
C2—C1—C6120.6 (3)C5—C6—C1120.1 (3)
C2—C1—P1121.8 (2)C5—C6—H6120.0
C6—C1—P1117.7 (2)C1—C6—H6120.0
C1—C2—C3118.5 (4)P1—C7—H7A109.5
C1—C2—H2120.8P1—C7—H7B109.5
C3—C2—H2120.8H7A—C7—H7B109.5
C4—C3—C2120.5 (4)P1—C7—H7C109.5
C4—C3—H3119.8H7A—C7—H7C109.5
C2—C3—H3119.8H7B—C7—H7C109.5
C7i—P1—C1—C2106.9 (2)P1—C1—C2—C3178.3 (2)
C7—P1—C1—C213.4 (3)C1—C2—C3—C40.4 (5)
C1i—P1—C1—C2132.3 (3)C2—C3—C4—C50.4 (5)
C7i—P1—C1—C671.5 (2)C3—C4—C5—C60.0 (5)
C7—P1—C1—C6168.29 (19)C4—C5—C6—C10.4 (4)
C1i—P1—C1—C649.31 (17)C2—C1—C6—C50.4 (4)
C6—C1—C2—C30.0 (4)P1—C1—C6—C5178.8 (2)
Symmetry code: (i) y+1, x+1, z+5/6.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7C···I1ii0.983.013.983 (2)174
Symmetry code: (ii) xy+1, x, z+1/6.
 

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