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The title compound consists of C18H15PH+·ClO4 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806054110/ci2247sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806054110/ci2247Isup2.hkl
Contains datablock I

CCDC reference: 633657

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](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

Computing details top

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+·ClO4F(000) = 752
Mr = 362.73Dx = 1.379 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 1802 reflections
a = 10.6695 (18) Åθ = 2.5–20.1°
b = 13.113 (2) ŵ = 0.33 mm1
c = 12.488 (2) ÅT = 294 K
V = 1747.2 (5) Å3Block, colourless
Z = 40.12 × 0.10 × 0.06 mm
Data collection top
Bruker APEX area-detector
diffractometer
1725 independent reflections
Radiation source: fine-focus sealed tube1270 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
φ and ω scansθmax = 25.7°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.958, Tmax = 0.981k = 1415
10334 measured reflectionsl = 915
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H 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 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.23 e Å3
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
P10.39902 (10)0.25000.22899 (9)0.0637 (4)
O10.4987 (5)0.75000.3202 (3)0.1374 (17)
O20.4920 (3)0.6608 (3)0.4775 (3)0.1478 (15)
O30.3194 (4)0.75000.4259 (3)0.1044 (12)
Cl10.45473 (12)0.75000.42426 (9)0.0753 (4)
C10.3096 (3)0.1361 (2)0.2401 (2)0.0612 (7)
C20.3221 (4)0.0748 (3)0.3293 (3)0.0910 (11)
H20.37560.09380.38460.109*
C40.1766 (4)0.0423 (3)0.2564 (4)0.0908 (11)
H40.13170.10290.26110.109*
C50.1637 (3)0.0182 (3)0.1697 (3)0.0850 (10)
H50.10900.00120.11540.102*
C60.2292 (3)0.1073 (2)0.1598 (3)0.0725 (9)
H60.21930.14800.09940.087*
C30.2548 (4)0.0147 (3)0.3361 (4)0.1040 (13)
H30.26330.05620.39600.125*
C70.4860 (4)0.25000.1069 (4)0.0684 (11)
C80.5212 (5)0.3391 (3)0.0599 (4)0.1217 (17)
H80.49840.40120.09020.146*
C90.5913 (5)0.3365 (4)0.0336 (5)0.141 (2)
H90.61400.39790.06540.169*
C100.6276 (6)0.25000.0800 (5)0.1071 (19)
H100.67600.25000.14190.129*
H10.472 (4)0.25000.307 (4)0.080 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0575 (6)0.0702 (7)0.0634 (7)0.0000.0109 (5)0.000
O10.196 (5)0.152 (4)0.064 (2)0.0000.033 (3)0.000
O20.133 (2)0.172 (3)0.139 (3)0.051 (2)0.014 (2)0.077 (2)
O30.095 (3)0.081 (2)0.138 (3)0.0000.017 (2)0.000
Cl10.0952 (9)0.0750 (7)0.0555 (6)0.0000.0020 (6)0.000
C10.0567 (15)0.0632 (17)0.0635 (18)0.0061 (13)0.0027 (13)0.0028 (13)
C20.090 (2)0.106 (3)0.077 (2)0.005 (2)0.0183 (19)0.023 (2)
C40.097 (3)0.062 (2)0.113 (3)0.0049 (18)0.019 (2)0.001 (2)
C50.087 (2)0.078 (2)0.090 (3)0.0080 (19)0.013 (2)0.016 (2)
C60.083 (2)0.0632 (18)0.071 (2)0.0020 (16)0.0113 (17)0.0025 (15)
C30.116 (3)0.089 (3)0.107 (3)0.009 (2)0.008 (3)0.039 (2)
C70.056 (2)0.078 (3)0.072 (3)0.0000.005 (2)0.000
C80.149 (4)0.085 (3)0.131 (4)0.030 (3)0.060 (3)0.014 (3)
C90.161 (5)0.122 (4)0.141 (5)0.030 (3)0.066 (4)0.019 (3)
C100.104 (4)0.132 (6)0.084 (4)0.0000.020 (3)0.000
Geometric parameters (Å, º) top
P1—C1i1.778 (3)C4—H40.93
P1—C11.778 (3)C5—C61.367 (4)
P1—C71.785 (5)C5—H50.93
P1—H11.25 (5)C6—H60.93
O1—Cl11.382 (4)C3—H30.93
O2—Cl11.404 (3)C7—C8i1.360 (5)
O3—Cl11.444 (4)C7—C81.360 (5)
Cl1—O2ii1.404 (3)C8—C91.388 (6)
C1—C61.373 (4)C8—H80.93
C1—C21.380 (4)C9—C101.331 (6)
C2—C31.378 (5)C9—H90.93
C2—H20.93C10—C9i1.331 (6)
C4—C31.349 (5)C10—H100.93
C4—C51.349 (5)
C1i—P1—C1114.34 (19)C4—C5—C6121.5 (3)
C1i—P1—C7110.22 (12)C4—C5—H5119.2
C1—P1—C7110.22 (12)C6—C5—H5119.2
C1i—P1—H1105.8 (10)C1—C6—C5119.2 (3)
C1—P1—H1105.8 (10)C1—C6—H6120.4
C7—P1—H1110 (2)C5—C6—H6120.4
O1—Cl1—O2110.5 (2)C4—C3—C2120.4 (4)
O1—Cl1—O2ii110.5 (2)C4—C3—H3119.8
O2—Cl1—O2ii113.0 (4)C2—C3—H3119.8
O1—Cl1—O3110.7 (3)C8i—C7—C8118.4 (5)
O2—Cl1—O3106.03 (18)C8i—C7—P1120.8 (3)
O2ii—Cl1—O3106.03 (18)C8—C7—P1120.8 (3)
C6—C1—C2119.3 (3)C7—C8—C9119.4 (4)
C6—C1—P1120.6 (2)C7—C8—H8120.3
C2—C1—P1120.0 (3)C9—C8—H8120.3
C3—C2—C1119.7 (3)C10—C9—C8122.9 (5)
C3—C2—H2120.2C10—C9—H9118.5
C1—C2—H2120.2C8—C9—H9118.5
C3—C4—C5119.8 (4)C9—C10—C9i116.9 (6)
C3—C4—H4120.1C9—C10—H10121.5
C5—C4—H4120.1C9i—C10—H10121.5
Symmetry codes: (i) x, y+1/2, z; (ii) x, y+3/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2iii0.932.393.320 (5)174
C6—H6···O3iv0.932.583.507 (5)176
Symmetry codes: (iii) x+1, y1/2, z+1; (iv) x+1/2, y+1, z1/2.
 

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