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The reaction of phospho­rus pentachloride with p-tert-butyl­phenyl salicyl­ate yielded the title compound, C17H17Cl4O3P, which was originally thought to contain a P-O-C heterocycle. The true molecular structure has now been established by the determination of its crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804016289/fl6108sup1.cif
Contains datablocks global, 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804016289/fl61081sup2.hkl
Contains datablock 1

CCDC reference: 248777

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.025
  • wR factor = 0.069
  • Data-to-parameter ratio = 26.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT431_ALERT_2_C Short Inter HL..A Contact Cl3 .. Cl3 .. 3.42 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

(1) top
Crystal data top
C17H17Cl4O3PF(000) = 1808
Mr = 442.08Dx = 1.496 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 27.166 (2) ÅCell parameters from 8132 reflections
b = 5.9811 (5) Åθ = 2.2–30.5°
c = 24.158 (2) ŵ = 0.70 mm1
β = 90.944 (8)°T = 273 K
V = 3924.7 (6) Å3Block, colourless
Z = 80.30 × 0.29 × 0.23 mm
Data collection top
Bruker X8 APEX CCD area detector
diffractometer
5988 independent reflections
Radiation source: fine-focus sealed tube5358 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
φ and ω scansθmax = 30.5°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 1996)
h = 3838
Tmin = 0.818, Tmax = 0.859k = 88
60962 measured reflectionsl = 3434
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)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0327P)2 + 3.2995P]
where P = (Fo2 + 2Fc2)/3
5988 reflections(Δ/σ)max = 0.001
229 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = 0.42 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
Cl40.200052 (9)0.71226 (4)0.373034 (11)0.01940 (6)
Cl30.205345 (9)0.38244 (5)0.461396 (10)0.01996 (6)
Cl20.175260 (11)0.88158 (5)0.543468 (13)0.02884 (7)
Cl10.072379 (14)1.07744 (5)0.511177 (13)0.03343 (8)
P10.109345 (10)0.79097 (5)0.515584 (11)0.01665 (6)
O30.19826 (3)0.27940 (13)0.35503 (3)0.01636 (14)
O20.08542 (3)0.61912 (15)0.54841 (3)0.02300 (16)
O10.11955 (3)0.73374 (13)0.45310 (3)0.01923 (15)
C10.18091 (3)0.43453 (17)0.39198 (4)0.01403 (17)
C20.12529 (3)0.41515 (17)0.39318 (4)0.01433 (17)
C30.09591 (4)0.56082 (18)0.42358 (4)0.01589 (18)
C40.04495 (4)0.5418 (2)0.42382 (5)0.0207 (2)
H40.02610.64300.44360.025*
C50.02237 (4)0.3696 (2)0.39411 (5)0.0226 (2)
H50.01170.35470.39410.027*
C60.05076 (4)0.2204 (2)0.36445 (5)0.0225 (2)
H60.03570.10470.34480.027*
C70.10187 (4)0.24317 (19)0.36397 (4)0.01824 (19)
H70.12060.14230.34390.022*
C80.24898 (4)0.27338 (17)0.34249 (4)0.01523 (18)
C90.26444 (4)0.37789 (19)0.29469 (4)0.01792 (19)
H90.24260.46240.27330.022*
C100.31358 (4)0.35424 (18)0.27905 (4)0.01725 (19)
H100.32430.42510.24710.021*
C110.34693 (4)0.22652 (17)0.31033 (4)0.01445 (17)
C120.32975 (4)0.12488 (18)0.35869 (4)0.01695 (18)
H120.35150.04130.38050.020*
C130.28095 (4)0.14617 (18)0.37484 (4)0.01712 (18)
H130.27000.07630.40680.021*
C140.40068 (4)0.18858 (17)0.29389 (4)0.01578 (18)
C150.40976 (4)0.0649 (2)0.28827 (5)0.0240 (2)
H15A0.40370.13680.32300.036*
H15B0.44330.09050.27790.036*
H15C0.38800.12520.26030.036*
C160.41304 (4)0.3005 (2)0.23875 (5)0.0226 (2)
H16A0.39160.24380.21010.034*
H16B0.44660.26870.22970.034*
H16C0.40870.45930.24190.034*
C170.43511 (4)0.2843 (2)0.33924 (5)0.0210 (2)
H17A0.42950.44210.34280.032*
H17B0.46870.25860.32940.032*
H17C0.42860.21210.37380.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl40.02028 (11)0.01587 (11)0.02220 (12)0.00316 (9)0.00473 (9)0.00030 (9)
Cl30.01738 (11)0.02674 (13)0.01566 (11)0.00314 (9)0.00296 (8)0.00084 (9)
Cl20.02857 (14)0.03011 (15)0.02766 (14)0.00992 (11)0.00464 (11)0.00081 (11)
Cl10.05181 (19)0.02520 (14)0.02337 (13)0.02032 (13)0.00346 (12)0.00100 (11)
P10.01935 (12)0.01555 (12)0.01509 (12)0.00222 (9)0.00119 (9)0.00065 (9)
O30.0117 (3)0.0183 (3)0.0191 (3)0.0004 (3)0.0021 (2)0.0041 (3)
O20.0226 (4)0.0251 (4)0.0214 (4)0.0016 (3)0.0021 (3)0.0054 (3)
O10.0216 (4)0.0176 (4)0.0187 (3)0.0015 (3)0.0050 (3)0.0039 (3)
C10.0136 (4)0.0149 (4)0.0136 (4)0.0007 (3)0.0004 (3)0.0001 (3)
C20.0119 (4)0.0168 (4)0.0142 (4)0.0007 (3)0.0003 (3)0.0013 (3)
C30.0161 (4)0.0168 (4)0.0148 (4)0.0014 (4)0.0001 (3)0.0004 (3)
C40.0154 (4)0.0255 (5)0.0214 (5)0.0055 (4)0.0016 (4)0.0005 (4)
C50.0118 (4)0.0335 (6)0.0225 (5)0.0008 (4)0.0010 (4)0.0007 (4)
C60.0156 (5)0.0309 (6)0.0209 (5)0.0042 (4)0.0011 (4)0.0044 (4)
C70.0146 (4)0.0226 (5)0.0176 (4)0.0011 (4)0.0003 (3)0.0038 (4)
C80.0120 (4)0.0159 (4)0.0179 (4)0.0008 (3)0.0018 (3)0.0025 (4)
C90.0161 (4)0.0219 (5)0.0157 (4)0.0041 (4)0.0006 (3)0.0015 (4)
C100.0169 (4)0.0203 (5)0.0146 (4)0.0021 (4)0.0022 (3)0.0024 (4)
C110.0140 (4)0.0139 (4)0.0155 (4)0.0003 (3)0.0010 (3)0.0011 (3)
C120.0157 (4)0.0170 (4)0.0182 (4)0.0024 (4)0.0009 (3)0.0036 (4)
C130.0166 (4)0.0163 (4)0.0186 (4)0.0002 (4)0.0031 (3)0.0028 (4)
C140.0143 (4)0.0168 (4)0.0164 (4)0.0018 (3)0.0026 (3)0.0013 (3)
C150.0239 (5)0.0193 (5)0.0288 (6)0.0056 (4)0.0050 (4)0.0021 (4)
C160.0189 (5)0.0296 (6)0.0194 (5)0.0036 (4)0.0053 (4)0.0050 (4)
C170.0162 (4)0.0249 (5)0.0219 (5)0.0008 (4)0.0009 (4)0.0009 (4)
Geometric parameters (Å, º) top
Cl4—C11.802 (1)C9—C101.4006 (14)
Cl3—C11.820 (1)C9—H90.9300
Cl2—P11.9784 (4)C10—C111.3973 (14)
Cl1—P11.9880 (4)C10—H100.9300
P1—O21.4577 (9)C11—C121.4036 (14)
P1—O11.5768 (8)C11—C141.5366 (13)
O3—C11.376 (1)C12—C131.3940 (14)
O3—C81.416 (1)C12—H120.9300
O1—C31.4055 (13)C13—H130.9300
C1—C21.5162 (13)C14—C161.5329 (15)
C2—C71.3950 (14)C14—C171.5393 (15)
C2—C31.3982 (14)C14—C151.5423 (15)
C3—C41.3892 (14)C15—H15A0.9600
C4—C51.3919 (17)C15—H15B0.9600
C4—H40.9300C15—H15C0.9600
C5—C61.3868 (16)C16—H16A0.9600
C5—H50.9300C16—H16B0.9600
C6—C71.3952 (14)C16—H16C0.9600
C6—H60.9300C17—H17A0.9600
C7—H70.9300C17—H17B0.9600
C8—C91.3845 (14)C17—H17C0.9600
C8—C131.3862 (14)
O2—P1—O1117.05 (5)C10—C9—H9120.6
O2—P1—Cl2114.65 (4)C11—C10—C9121.44 (9)
O1—P1—Cl2102.30 (3)C11—C10—H10119.3
O2—P1—Cl1114.04 (4)C9—C10—H10119.3
O1—P1—Cl1103.44 (3)C10—C11—C12117.74 (9)
Cl2—P1—Cl1103.63 (2)C10—C11—C14123.46 (9)
C1—O3—C8120.05 (8)C12—C11—C14118.79 (9)
C3—O1—P1124.01 (7)C13—C12—C11121.62 (9)
O3—C1—C2108.24 (8)C13—C12—H12119.2
O3—C1—Cl4110.71 (7)C11—C12—H12119.2
C2—C1—Cl4111.54 (7)C8—C13—C12118.83 (9)
O3—C1—Cl3111.01 (7)C8—C13—H13120.6
C2—C1—Cl3108.52 (7)C12—C13—H13120.6
Cl4—C1—Cl3106.82 (5)C16—C14—C11112.50 (8)
C7—C2—C3117.75 (9)C16—C14—C17108.47 (9)
C7—C2—C1119.54 (9)C11—C14—C17109.27 (8)
C3—C2—C1122.69 (9)C16—C14—C15108.38 (9)
C4—C3—C2121.91 (10)C11—C14—C15108.78 (8)
C4—C3—O1120.36 (9)C17—C14—C15109.41 (9)
C2—C3—O1117.71 (9)C14—C15—H15A109.5
C3—C4—C5119.29 (10)C14—C15—H15B109.5
C3—C4—H4120.4H15A—C15—H15B109.5
C5—C4—H4120.4C14—C15—H15C109.5
C6—C5—C4119.90 (10)H15A—C15—H15C109.5
C6—C5—H5120.1H15B—C15—H15C109.5
C4—C5—H5120.1C14—C16—H16A109.5
C5—C6—C7120.23 (11)C14—C16—H16B109.5
C5—C6—H6119.9H16A—C16—H16B109.5
C7—C6—H6119.9C14—C16—H16C109.5
C2—C7—C6120.89 (10)H16A—C16—H16C109.5
C2—C7—H7119.6H16B—C16—H16C109.5
C6—C7—H7119.6C14—C17—H17A109.5
C9—C8—C13121.49 (9)C14—C17—H17B109.5
C9—C8—O3118.46 (9)H17A—C17—H17B109.5
C13—C8—O3119.74 (9)C14—C17—H17C109.5
C8—C9—C10118.88 (9)H17A—C17—H17C109.5
C8—C9—H9120.6H17B—C17—H17C109.5
 

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