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The title compound, C22H30ClO4PS, displays distorted tetra­hedral geometry around the P atom. The dihedral angle between the benzene rings is 41.2 (2)°. Because of the steric effects of the tert-but­yl groups, the aromatic rings have unusual endocyclic angles. The mol­ecules are linked by weak C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805021860/bt6694sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805021860/bt6694Isup2.hkl
Contains datablock I

CCDC reference: 282242

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.027
  • wR factor = 0.073
  • Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for Cl1 - P1 .. 18.55 su PLAT230_ALERT_2_B Hirshfeld Test Diff for S1 - P1 .. 17.74 su
Alert level C PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ? PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.64 mm PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C7 - C8 .. 6.77 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C22 - C27 .. 5.42 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C27 - C29 .. 5.20 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C27 - C30 .. 5.22 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT732_ALERT_1_C Angle Calc 97.13(18), Rep 97.13(5) ...... 3.60 su-Rat O3 -P1 -O1 1.555 1.555 1.555 PLAT732_ALERT_1_C Angle Calc 113.24(5), Rep 113.24(2) ...... 2.50 su-Rat S1 -P1 -CL1 1.555 1.555 1.555
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 26.00 From the CIF: _reflns_number_total 4630 Count of symmetry unique reflns 2327 Completeness (_total/calc) 198.97% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2303 Fraction of Friedel pairs measured 0.990 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

O,O-Bis(2-tert-butyl-4-methoxyphenyl) chlorothiophosphonate top
Crystal data top
C22H30ClO4PSF(000) = 968
Mr = 456.94Dx = 1.286 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C-2ycCell parameters from 16485 reflections
a = 23.592 (3) Åθ = 1.7–26.7°
b = 8.3111 (6) ŵ = 0.34 mm1
c = 12.5067 (14) ÅT = 150 K
β = 105.740 (9)°Prism, colorless
V = 2360.3 (4) Å30.64 × 0.59 × 0.55 mm
Z = 4
Data collection top
Stoe IPDS-II
diffractometer
4160 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scansθmax = 26.0°, θmin = 1.8°
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
h = 2828
Tmin = 0.824, Tmax = 0.869k = 1010
16485 measured reflectionsl = 1515
4630 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.027 w = 1/[σ2(Fo2) + (0.0348P)2 + 1.103P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.074(Δ/σ)max < 0.001
S = 1.12Δρmax = 0.18 e Å3
4630 reflectionsΔρmin = 0.23 e Å3
270 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction coefficient: 0.0038 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier map
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
C10.61457 (18)0.2884 (5)0.7043 (4)0.0233 (9)
C20.65778 (19)0.4160 (5)0.7298 (4)0.0247 (9)
C30.70775 (18)0.3899 (5)0.8108 (4)0.0248 (9)
H30.73580.47110.83020.030*
C40.71839 (19)0.2351 (5)0.8684 (4)0.0247 (9)
C50.67790 (18)0.1184 (5)0.8424 (3)0.0278 (9)
H50.68460.02060.87980.033*
C60.62496 (18)0.1431 (5)0.7584 (4)0.0255 (9)
H60.59720.06120.73970.031*
C70.6451 (2)0.5797 (5)0.6695 (4)0.0303 (10)
C80.6370 (2)0.5587 (6)0.5439 (5)0.0422 (13)
H8A0.62720.66060.50730.063*
H8B0.60580.48330.51460.063*
H8C0.67290.51930.53140.063*
C90.5908 (2)0.6681 (6)0.6915 (5)0.0426 (12)
H9A0.58350.76610.64940.064*
H9B0.59870.69250.76920.064*
H9C0.55670.59990.66950.064*
C100.6987 (2)0.6971 (5)0.7079 (5)0.0448 (13)
H10A0.73270.65020.69200.067*
H10B0.70660.71590.78630.067*
H10C0.68950.79730.66880.067*
C110.81095 (19)0.3284 (6)0.9857 (4)0.0352 (11)
H11A0.82620.35930.92490.053*
H11B0.84260.29111.04630.053*
H11C0.79240.41941.00930.053*
C210.43699 (17)0.2962 (5)0.3639 (3)0.0221 (9)
C220.39781 (17)0.4218 (5)0.3432 (4)0.0218 (8)
C230.34387 (17)0.3852 (6)0.2561 (4)0.0262 (9)
H230.31480.46370.23740.031*
C240.33435 (18)0.2455 (5)0.2022 (4)0.0258 (9)
C250.37774 (17)0.1167 (5)0.2299 (4)0.0275 (9)
H250.37050.01710.19500.033*
C260.42902 (19)0.1464 (5)0.3079 (4)0.0266 (9)
H260.45870.06920.32460.032*
C270.4071 (2)0.5872 (5)0.4031 (4)0.0288 (10)
C280.3544 (2)0.6996 (6)0.3601 (5)0.0480 (15)
H28A0.34820.71710.28190.072*
H28B0.36200.80070.39850.072*
H28C0.31980.65150.37300.072*
C290.4615 (2)0.6646 (6)0.3781 (4)0.0393 (12)
H29A0.45550.67090.29920.059*
H29B0.49570.60040.41030.059*
H29C0.46710.77090.40930.059*
C300.4163 (2)0.5632 (5)0.5296 (4)0.0339 (11)
H30A0.41930.66630.56540.051*
H30B0.45190.50350.55990.051*
H30C0.38350.50510.54200.051*
C310.24133 (18)0.3299 (6)0.0825 (4)0.0361 (11)
H31A0.22530.35640.14310.054*
H31B0.21040.29230.02070.054*
H31C0.25920.42380.06090.054*
O10.56202 (13)0.3195 (4)0.6223 (3)0.0260 (7)
O20.76883 (13)0.2027 (4)0.9508 (3)0.0324 (8)
O30.49314 (14)0.3197 (4)0.4458 (3)0.0260 (7)
O40.28530 (14)0.2050 (4)0.1170 (3)0.0323 (8)
P10.52627 (7)0.19436 (4)0.53408 (15)0.02670 (10)
S10.47221 (3)0.06319 (14)0.59405 (6)0.0310 (2)
Cl10.58094 (3)0.06347 (14)0.47391 (6)0.0333 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0212 (18)0.0200 (17)0.028 (2)0.0072 (14)0.0050 (17)0.0089 (15)
C20.030 (2)0.0183 (17)0.027 (2)0.0026 (15)0.0107 (17)0.0007 (15)
C30.032 (2)0.0196 (18)0.026 (2)0.0043 (16)0.0131 (17)0.0005 (16)
C40.031 (2)0.0233 (18)0.0188 (19)0.0071 (15)0.0050 (16)0.0058 (14)
C50.031 (2)0.032 (2)0.0151 (18)0.0094 (16)0.0026 (15)0.0054 (15)
C60.0203 (19)0.029 (2)0.025 (2)0.0026 (17)0.0009 (16)0.0022 (18)
C70.030 (2)0.025 (2)0.031 (2)0.0076 (16)0.0018 (18)0.0044 (16)
C80.043 (3)0.033 (2)0.051 (3)0.0048 (19)0.014 (2)0.017 (2)
C90.034 (2)0.030 (2)0.061 (3)0.0113 (19)0.008 (2)0.002 (2)
C100.052 (3)0.026 (2)0.050 (3)0.007 (2)0.003 (3)0.001 (2)
C110.030 (2)0.040 (2)0.033 (3)0.0088 (18)0.0044 (19)0.008 (2)
C210.0208 (18)0.029 (2)0.0136 (18)0.0064 (15)0.0008 (15)0.0056 (14)
C220.0191 (18)0.0264 (19)0.0177 (18)0.0007 (14)0.0012 (14)0.0044 (14)
C230.0169 (16)0.032 (2)0.025 (2)0.0040 (16)0.0022 (15)0.0073 (18)
C240.0156 (16)0.038 (2)0.022 (2)0.0076 (15)0.0020 (15)0.0110 (16)
C250.028 (2)0.0211 (19)0.034 (2)0.0088 (15)0.0098 (17)0.0007 (16)
C260.030 (2)0.022 (2)0.027 (2)0.0067 (17)0.0070 (18)0.0021 (17)
C270.033 (2)0.0173 (17)0.035 (2)0.0005 (16)0.0067 (18)0.0087 (15)
C280.038 (3)0.032 (3)0.064 (4)0.017 (2)0.004 (3)0.015 (2)
C290.057 (3)0.0195 (19)0.039 (3)0.002 (2)0.009 (2)0.0026 (19)
C300.045 (3)0.034 (2)0.0201 (19)0.0029 (19)0.0051 (18)0.0041 (16)
C310.023 (2)0.043 (3)0.033 (3)0.0120 (18)0.0083 (18)0.009 (2)
O10.0192 (14)0.0256 (15)0.0272 (16)0.0020 (11)0.0038 (12)0.0011 (11)
O20.0215 (15)0.0403 (19)0.0300 (19)0.0026 (13)0.0023 (14)0.0009 (14)
O30.0286 (16)0.0201 (14)0.0252 (16)0.0014 (11)0.0001 (12)0.0024 (11)
O40.0294 (16)0.0328 (18)0.0275 (18)0.0006 (13)0.0046 (15)0.0007 (13)
P10.02940 (19)0.01983 (17)0.02479 (18)0.0009 (6)0.00303 (14)0.0009 (6)
S10.0249 (5)0.0366 (6)0.0313 (6)0.0061 (4)0.0070 (4)0.0018 (5)
Cl10.0286 (6)0.0384 (6)0.0333 (6)0.0069 (4)0.0092 (5)0.0030 (5)
Geometric parameters (Å, º) top
C1—C61.373 (6)C21—O31.451 (5)
C1—O11.402 (5)C22—C231.465 (6)
C1—C21.446 (5)C22—C271.553 (6)
C2—C31.347 (6)C23—C241.330 (6)
C2—C71.545 (6)C23—H230.9300
C3—C41.463 (6)C24—O41.385 (5)
C3—H30.9300C24—C251.457 (5)
C4—C51.338 (6)C25—C261.355 (6)
C4—O21.373 (5)C25—H250.9300
C5—C61.412 (5)C26—H260.9300
C5—H50.9300C27—C281.533 (6)
C6—H60.9300C27—C291.540 (7)
C7—C81.540 (8)C27—C301.551 (7)
C7—C101.565 (6)C28—H28A0.9600
C7—C91.566 (7)C28—H28B0.9600
C8—H8A0.9600C28—H28C0.9600
C8—H8B0.9600C29—H29A0.9600
C8—H8C0.9600C29—H29B0.9600
C9—H9A0.9600C29—H29C0.9600
C9—H9B0.9600C30—H30A0.9600
C9—H9C0.9600C30—H30B0.9600
C10—H10A0.9600C30—H30C0.9600
C10—H10B0.9600C31—O41.448 (5)
C10—H10C0.9600C31—H31A0.9600
C11—O21.427 (6)C31—H31B0.9600
C11—H11A0.9600C31—H31C0.9600
C11—H11B0.9600O1—P11.583 (3)
C11—H11C0.9600O3—P11.564 (3)
C21—C221.372 (5)P1—S11.9740 (18)
C21—C261.416 (6)P1—Cl11.9848 (18)
C6—C1—O1121.8 (4)C23—C22—C27121.6 (4)
C6—C1—C2121.0 (4)C24—C23—C22123.4 (4)
O1—C1—C2117.2 (4)C24—C23—H23118.3
C3—C2—C1117.9 (4)C22—C23—H23118.3
C3—C2—C7121.5 (4)C23—C24—O4126.3 (4)
C1—C2—C7120.5 (4)C23—C24—C25120.7 (4)
C2—C3—C4120.7 (4)O4—C24—C25113.0 (4)
C2—C3—H3119.7C26—C25—C24118.0 (4)
C4—C3—H3119.7C26—C25—H25121.0
C5—C4—O2117.2 (4)C24—C25—H25121.0
C5—C4—C3120.1 (4)C25—C26—C21119.3 (4)
O2—C4—C3122.7 (4)C25—C26—H26120.4
C4—C5—C6120.3 (4)C21—C26—H26120.4
C4—C5—H5119.8C28—C27—C29108.4 (4)
C6—C5—H5119.8C28—C27—C30108.1 (4)
C1—C6—C5119.9 (4)C29—C27—C30111.5 (4)
C1—C6—H6120.1C28—C27—C22112.0 (4)
C5—C6—H6120.1C29—C27—C22106.8 (4)
C8—C7—C2110.7 (4)C30—C27—C22109.9 (4)
C8—C7—C10104.5 (4)C27—C28—H28A109.5
C2—C7—C10111.5 (4)C27—C28—H28B109.5
C8—C7—C9110.6 (4)H28A—C28—H28B109.5
C2—C7—C9112.7 (4)C27—C28—H28C109.5
C10—C7—C9106.5 (4)H28A—C28—H28C109.5
C7—C8—H8A109.5H28B—C28—H28C109.5
C7—C8—H8B109.5C27—C29—H29A109.5
H8A—C8—H8B109.5C27—C29—H29B109.5
C7—C8—H8C109.5H29A—C29—H29B109.5
H8A—C8—H8C109.5C27—C29—H29C109.5
H8B—C8—H8C109.5H29A—C29—H29C109.5
C7—C9—H9A109.5H29B—C29—H29C109.5
C7—C9—H9B109.5C27—C30—H30A109.5
H9A—C9—H9B109.5C27—C30—H30B109.5
C7—C9—H9C109.5H30A—C30—H30B109.5
H9A—C9—H9C109.5C27—C30—H30C109.5
H9B—C9—H9C109.5H30A—C30—H30C109.5
C7—C10—H10A109.5H30B—C30—H30C109.5
C7—C10—H10B109.5O4—C31—H31A109.5
H10A—C10—H10B109.5O4—C31—H31B109.5
C7—C10—H10C109.5H31A—C31—H31B109.5
H10A—C10—H10C109.5O4—C31—H31C109.5
H10B—C10—H10C109.5H31A—C31—H31C109.5
O2—C11—H11A109.5H31B—C31—H31C109.5
O2—C11—H11B109.5C1—O1—P1126.0 (3)
H11A—C11—H11B109.5C4—O2—C11118.4 (4)
O2—C11—H11C109.5C21—O3—P1126.4 (3)
H11A—C11—H11C109.5C24—O4—C31115.9 (3)
H11B—C11—H11C109.5O3—P1—O197.13 (5)
C22—C21—C26125.7 (4)O3—P1—S1112.66 (14)
C22—C21—O3118.0 (3)O1—P1—S1112.02 (15)
C26—C21—O3116.2 (4)O3—P1—Cl1110.44 (15)
C21—C22—C23112.8 (4)O1—P1—Cl1110.26 (14)
C21—C22—C27125.6 (4)S1—P1—Cl1113.24 (2)
C6—C1—C2—C32.2 (7)C22—C23—C24—C251.6 (7)
O1—C1—C2—C3178.0 (4)C23—C24—C25—C263.1 (7)
C6—C1—C2—C7179.2 (4)O4—C24—C25—C26176.4 (4)
O1—C1—C2—C71.0 (6)C24—C25—C26—C213.8 (6)
C1—C2—C3—C41.8 (6)C22—C21—C26—C253.2 (7)
C7—C2—C3—C4178.8 (4)O3—C21—C26—C25179.6 (4)
C2—C3—C4—C51.2 (7)C21—C22—C27—C28179.6 (5)
C2—C3—C4—O2179.5 (4)C23—C22—C27—C280.2 (7)
O2—C4—C5—C6179.9 (4)C21—C22—C27—C2961.8 (6)
C3—C4—C5—C60.8 (7)C23—C22—C27—C29118.4 (4)
O1—C1—C6—C5178.4 (4)C21—C22—C27—C3059.3 (6)
C2—C1—C6—C51.7 (7)C23—C22—C27—C30120.5 (5)
C4—C5—C6—C11.1 (7)C6—C1—O1—P136.4 (6)
C3—C2—C7—C8120.6 (5)C2—C1—O1—P1143.4 (3)
C1—C2—C7—C862.5 (6)C5—C4—O2—C11175.7 (4)
C3—C2—C7—C104.7 (7)C3—C4—O2—C113.7 (6)
C1—C2—C7—C10178.4 (4)C22—C21—O3—P1139.9 (4)
C3—C2—C7—C9115.0 (5)C26—C21—O3—P143.4 (5)
C1—C2—C7—C961.9 (6)C23—C24—O4—C311.7 (6)
C26—C21—C22—C231.5 (6)C25—C24—O4—C31177.8 (4)
O3—C21—C22—C23177.8 (4)C21—O3—P1—O1154.2 (3)
C26—C21—C22—C27178.7 (4)C21—O3—P1—S136.7 (4)
O3—C21—C22—C272.4 (7)C21—O3—P1—Cl191.0 (3)
C21—C22—C23—C240.7 (6)C1—O1—P1—O3157.0 (3)
C27—C22—C23—C24179.5 (4)C1—O1—P1—S185.0 (3)
C22—C23—C24—O4177.9 (4)C1—O1—P1—Cl142.1 (4)
 

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