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The title compound consists of C
18H
15PH
+·ClO
4− ion pairs, each ion lying on a crystallographic mirror plane. The P atom has a slightly distorted tetrahedral geometry. The P—H distance is 1.25 (5) Å. C—H
O hydrogen bonds are observed between the cation and anion.
Supporting information
CCDC reference: 633657
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.006 Å
- R factor = 0.053
- wR factor = 0.149
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT331_ALERT_2_B Small Average Phenyl C-C Dist. C7 -C8_b 1.36 Ang.
Alert level C
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1 -C6 1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.
Triphenylphosphonium perchlorate
top
Crystal data top
C18H16P+·ClO4− | F(000) = 752 |
Mr = 362.73 | Dx = 1.379 Mg m−3 |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 1802 reflections |
a = 10.6695 (18) Å | θ = 2.5–20.1° |
b = 13.113 (2) Å | µ = 0.33 mm−1 |
c = 12.488 (2) Å | T = 294 K |
V = 1747.2 (5) Å3 | Block, colourless |
Z = 4 | 0.12 × 0.10 × 0.06 mm |
Data collection top
Bruker APEX area-detector diffractometer | 1725 independent reflections |
Radiation source: fine-focus sealed tube | 1270 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
φ and ω scans | θmax = 25.7°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.958, Tmax = 0.981 | k = −14→15 |
10334 measured reflections | l = −9→15 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0909P)2 + 0.6474P] where P = (Fo2 + 2Fc2)/3 |
1725 reflections | (Δ/σ)max = 0.001 |
121 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−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 | x | y | z | Uiso*/Ueq | |
P1 | 0.39902 (10) | 0.2500 | 0.22899 (9) | 0.0637 (4) | |
O1 | 0.4987 (5) | 0.7500 | 0.3202 (3) | 0.1374 (17) | |
O2 | 0.4920 (3) | 0.6608 (3) | 0.4775 (3) | 0.1478 (15) | |
O3 | 0.3194 (4) | 0.7500 | 0.4259 (3) | 0.1044 (12) | |
Cl1 | 0.45473 (12) | 0.7500 | 0.42426 (9) | 0.0753 (4) | |
C1 | 0.3096 (3) | 0.1361 (2) | 0.2401 (2) | 0.0612 (7) | |
C2 | 0.3221 (4) | 0.0748 (3) | 0.3293 (3) | 0.0910 (11) | |
H2 | 0.3756 | 0.0938 | 0.3846 | 0.109* | |
C4 | 0.1766 (4) | −0.0423 (3) | 0.2564 (4) | 0.0908 (11) | |
H4 | 0.1317 | −0.1029 | 0.2611 | 0.109* | |
C5 | 0.1637 (3) | 0.0182 (3) | 0.1697 (3) | 0.0850 (10) | |
H5 | 0.1090 | −0.0012 | 0.1154 | 0.102* | |
C6 | 0.2292 (3) | 0.1073 (2) | 0.1598 (3) | 0.0725 (9) | |
H6 | 0.2193 | 0.1480 | 0.0994 | 0.087* | |
C3 | 0.2548 (4) | −0.0147 (3) | 0.3361 (4) | 0.1040 (13) | |
H3 | 0.2633 | −0.0562 | 0.3960 | 0.125* | |
C7 | 0.4860 (4) | 0.2500 | 0.1069 (4) | 0.0684 (11) | |
C8 | 0.5212 (5) | 0.3391 (3) | 0.0599 (4) | 0.1217 (17) | |
H8 | 0.4984 | 0.4012 | 0.0902 | 0.146* | |
C9 | 0.5913 (5) | 0.3365 (4) | −0.0336 (5) | 0.141 (2) | |
H9 | 0.6140 | 0.3979 | −0.0654 | 0.169* | |
C10 | 0.6276 (6) | 0.2500 | −0.0800 (5) | 0.1071 (19) | |
H10 | 0.6760 | 0.2500 | −0.1419 | 0.129* | |
H1 | 0.472 (4) | 0.2500 | 0.307 (4) | 0.080 (13)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0575 (6) | 0.0702 (7) | 0.0634 (7) | 0.000 | −0.0109 (5) | 0.000 |
O1 | 0.196 (5) | 0.152 (4) | 0.064 (2) | 0.000 | 0.033 (3) | 0.000 |
O2 | 0.133 (2) | 0.172 (3) | 0.139 (3) | 0.051 (2) | 0.014 (2) | 0.077 (2) |
O3 | 0.095 (3) | 0.081 (2) | 0.138 (3) | 0.000 | −0.017 (2) | 0.000 |
Cl1 | 0.0952 (9) | 0.0750 (7) | 0.0555 (6) | 0.000 | 0.0020 (6) | 0.000 |
C1 | 0.0567 (15) | 0.0632 (17) | 0.0635 (18) | 0.0061 (13) | −0.0027 (13) | 0.0028 (13) |
C2 | 0.090 (2) | 0.106 (3) | 0.077 (2) | −0.005 (2) | −0.0183 (19) | 0.023 (2) |
C4 | 0.097 (3) | 0.062 (2) | 0.113 (3) | −0.0049 (18) | 0.019 (2) | 0.001 (2) |
C5 | 0.087 (2) | 0.078 (2) | 0.090 (3) | −0.0080 (19) | −0.013 (2) | −0.016 (2) |
C6 | 0.083 (2) | 0.0632 (18) | 0.071 (2) | −0.0020 (16) | −0.0113 (17) | 0.0025 (15) |
C3 | 0.116 (3) | 0.089 (3) | 0.107 (3) | −0.009 (2) | −0.008 (3) | 0.039 (2) |
C7 | 0.056 (2) | 0.078 (3) | 0.072 (3) | 0.000 | −0.005 (2) | 0.000 |
C8 | 0.149 (4) | 0.085 (3) | 0.131 (4) | −0.030 (3) | 0.060 (3) | −0.014 (3) |
C9 | 0.161 (5) | 0.122 (4) | 0.141 (5) | −0.030 (3) | 0.066 (4) | 0.019 (3) |
C10 | 0.104 (4) | 0.132 (6) | 0.084 (4) | 0.000 | 0.020 (3) | 0.000 |
Geometric parameters (Å, º) top
P1—C1i | 1.778 (3) | C4—H4 | 0.93 |
P1—C1 | 1.778 (3) | C5—C6 | 1.367 (4) |
P1—C7 | 1.785 (5) | C5—H5 | 0.93 |
P1—H1 | 1.25 (5) | C6—H6 | 0.93 |
O1—Cl1 | 1.382 (4) | C3—H3 | 0.93 |
O2—Cl1 | 1.404 (3) | C7—C8i | 1.360 (5) |
O3—Cl1 | 1.444 (4) | C7—C8 | 1.360 (5) |
Cl1—O2ii | 1.404 (3) | C8—C9 | 1.388 (6) |
C1—C6 | 1.373 (4) | C8—H8 | 0.93 |
C1—C2 | 1.380 (4) | C9—C10 | 1.331 (6) |
C2—C3 | 1.378 (5) | C9—H9 | 0.93 |
C2—H2 | 0.93 | C10—C9i | 1.331 (6) |
C4—C3 | 1.349 (5) | C10—H10 | 0.93 |
C4—C5 | 1.349 (5) | | |
| | | |
C1i—P1—C1 | 114.34 (19) | C4—C5—C6 | 121.5 (3) |
C1i—P1—C7 | 110.22 (12) | C4—C5—H5 | 119.2 |
C1—P1—C7 | 110.22 (12) | C6—C5—H5 | 119.2 |
C1i—P1—H1 | 105.8 (10) | C1—C6—C5 | 119.2 (3) |
C1—P1—H1 | 105.8 (10) | C1—C6—H6 | 120.4 |
C7—P1—H1 | 110 (2) | C5—C6—H6 | 120.4 |
O1—Cl1—O2 | 110.5 (2) | C4—C3—C2 | 120.4 (4) |
O1—Cl1—O2ii | 110.5 (2) | C4—C3—H3 | 119.8 |
O2—Cl1—O2ii | 113.0 (4) | C2—C3—H3 | 119.8 |
O1—Cl1—O3 | 110.7 (3) | C8i—C7—C8 | 118.4 (5) |
O2—Cl1—O3 | 106.03 (18) | C8i—C7—P1 | 120.8 (3) |
O2ii—Cl1—O3 | 106.03 (18) | C8—C7—P1 | 120.8 (3) |
C6—C1—C2 | 119.3 (3) | C7—C8—C9 | 119.4 (4) |
C6—C1—P1 | 120.6 (2) | C7—C8—H8 | 120.3 |
C2—C1—P1 | 120.0 (3) | C9—C8—H8 | 120.3 |
C3—C2—C1 | 119.7 (3) | C10—C9—C8 | 122.9 (5) |
C3—C2—H2 | 120.2 | C10—C9—H9 | 118.5 |
C1—C2—H2 | 120.2 | C8—C9—H9 | 118.5 |
C3—C4—C5 | 119.8 (4) | C9—C10—C9i | 116.9 (6) |
C3—C4—H4 | 120.1 | C9—C10—H10 | 121.5 |
C5—C4—H4 | 120.1 | C9i—C10—H10 | 121.5 |
Symmetry codes: (i) x, −y+1/2, z; (ii) x, −y+3/2, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O2iii | 0.93 | 2.39 | 3.320 (5) | 174 |
C6—H6···O3iv | 0.93 | 2.58 | 3.507 (5) | 176 |
Symmetry codes: (iii) −x+1, y−1/2, −z+1; (iv) −x+1/2, −y+1, z−1/2. |
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