addenda and errata\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

O,O-Bis(2-tert-butyl-4-meth­oxy­phen­yl) chloro­thio­phospho­nate. Corrigendum.

CROSSMARK_Color_square_no_text.svg

aDepartment of Chemistry, Ondokuz Mayıs University, TR-55139 Samsun, Turkey, and bDepartment of Physics, Ondokuz Mayıs University, TR-55139 Samsun, Turkey
*Correspondence e-mail: orhanb@omu.edu.tr

(Received 8 August 2005; accepted 5 September 2005; online 17 September 2005)

In the original report by Odabaşoğlu, Büyükgüngör & Albayrak [Acta Cryst. (2005), E61, o2528–o2530], the structure was reported in the incorrect space group Cc. The structure is now reported as disordered in the correct space group C2/c. The P atom lies on a twofold rotation axis.A revised description of the hydrogen bonding is also given.

1. Comment

An ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) view of (I) and a packing diagram are shown in Figs. 1[link] and 2[link], respectively. The P atom lies on a twofold rotation axis, eading to disorder of the Cl and S atoms. Compound (I) has no classical hydrogen bonds, but there are two C—H⋯π inter­actions: H8ACg1= 3.12 (2) Å and C8—H8ACg1 = 122.8 (2)° (Cg1 is the centroid of the C1ii–C6ii ring), and H11ACg2 = 2.71 (2) Å and C11—H11ACg2 = 142.7 (1)° (Cg2 is the centroid of the C1iii–C6iii ring) [symmetry codes: (ii) x, 1 − y, [{1\over 2}] + z; (iii) [{1\over 2}]x, [{1\over 2}]y, − z]. The dihedral angle between the symmetry-related benzene rings is 41.2 (2)°. Selected bond distances and angles are given in Table 1[link].

[Figure 1]
Figure 1
A view of (I), with the atom-numbering scheme and 50% probability displacement ellipsoids·[Symmetry code: (i) −x + 1, y, −z + [{1\over 2}]]
[Figure 2]
Figure 2
A view of the packing of (I); C—H⋯π inter­actions are drawn as dashed lines.

2. Experimental

2.1.1. Crystal data
  • C22H30ClO4PS

  • Mr = 456.94

  • Monoclinic, C 2/c

  • a = 23.592 (3) Å

  • b = 8.3111 (6) Å

  • c = 12.5067 (14) Å

  • β = 105.740 (9)°

  • V = 2360.3 (4) Å3

  • Z = 4

  • Dx = 1.286 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 16485 reflections

  • θ = 1.7–26.7°

  • μ = 0.34 mm−1

  • T = 150 K

  • Prism, colorless

  • 0.64 × 0.59 × 0.55 mm

2.1.2. Data collection
  • Stoe IPDS-II diffractometer

  • ω scans

  • Absorption correction: integration(X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA (Version 1.18) and X-RED32 (Version 1.04). Stoe & Cie, Darmstadt, Germany.])Tmin = 0.824, Tmax = 0.869

  • 16485 measured reflections

  • 2327 independent reflections

  • 2146 reflections with I > 2σ(I)

  • Rint = 0.032

  • θmax = 26.0°

  • h = −28 → 28

  • k = −10 → 10

  • l = −15 → 15

2.1.3. Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.028

  • wR(F2) = 0.073

  • S = 1.08

  • 2327 reflections

  • 192 parameters

  • All H-atom parameters refined

  • w = 1/[σ2(Fo2) + (0.0362P)2 + 1.6163P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max = 0.002

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Selected geometric parameters (Å, °)

C1—C2 1.3946 (18)
C1—C6 1.4086 (17)
C1—O1 1.4226 (14)
C2—C3 1.3860 (18)
C3—C4 1.3979 (18)
C4—C5 1.4017 (19)
C5—C6 1.4088 (18)
O1—P1 1.5750 (9)
P1—S1i 1.9791 (4)
P1—Cl1 1.9791 (4)
C2—C1—C6 123.25 (11)
C2—C1—O1 119.13 (11)
C6—C1—O1 117.58 (11)
C3—C2—C1 119.77 (12)
C2—C3—C4 119.11 (12)
C3—C4—C5 120.39 (11)
C4—C5—C6 121.99 (12)
C1—C6—C5 115.48 (11)
O1—P1—O1i 97.08 (7)
O1—P1—S1i 111.27 (4)
O1—P1—Cl1 111.44 (3)
S1i—P1—Cl1 113.26 (3)
Symmetry code: (i) [-x+1, y, -z+{\script{1\over 2}}].

All H atoms were refined freely. Atoms S1 and Cl1 were assigned to the same atomic site and refined freely with the same atomic coordinates and with fixed site-occupancy factors of 0.5.

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA (Version 1.18) and X-RED32 (Version 1.04). Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA (Version 1.18) and X-RED32 (Version 1.04). Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

An ORTEP-3 (Farrugia, 1997) view of (I) and a packing diagram are shown in Figs. 1 and 2, respectively. Compound (I) has no classical hydrogen bonds but there are two C—H···π interactions: H8A···Cg1= 3.12 (2) Å and C8—H8A···Cg1 = 122.8 (2)° [Cg1 is the centroid of the C1i–C6i ring; and H11A···Cg2 = 2.71 (2) Å and C11—H11A···Cg2 = 142.7 (1)° (Cg2 is the centroid of the C1ii–C6ii ring); symmetry codes: (i) x, 1 − y, 1/2 + z; (ii) 1/2 − x, 1/2 − y, − z]. The dihedral angle between the symmetry-related benzene rings in (I) is 41.2 (2)°. Selected bond distances and angles for (I) are given in Table 1. The benzene ring is planar, with a maximum deviation from the plane defined by the six ring atoms of 0.007 (1) Å (for C3).

Experimental top

Compound (I) was prepared by the method of Odabaşoǧlu et al. (2005), using 2-tert-butyl-4-methoxyphenol and PSCl3 as starting materials. Crystals of (I) suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution in n-hexane (yield 77%, m.p. 423 K). Analysis calculated: C 57.83, H 6.57%; found: C 57.36, H 6.38%.

Refinement top

All H atoms were refined freely. Atoms S1 and Cl1 were assigned to the same atomic site and refined freely with the same atomic coordinates and with fixed site-occupancy factors of 0.5.

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).

Figures top
[Figure 1] Fig. 1. A view of (I), with the atom-numbering scheme and 50% probability displacement ellipsoids·[Symmetry codes: (i) −x, y, −z + 1/2]
[Figure 2] Fig. 2. A view of the packing of (I); C—H···π interactions are drawn as dashed lines.
O,O-Bis(2-tert-butyl-4-methoxyphenyl) chlorothiophosphonate top
Crystal data top
C22H30ClO4PSF(000) = 968
Mr = 456.94Dx = 1.286 Mg m3
Monoclinic, C2/cMo 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
2146 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
2327 independent reflections
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)] = 0.028Hydrogen site location: difference Fourier map
wR(F2) = 0.073All H-atom parameters refined
S = 1.08 w = 1/[σ2(Fo2) + (0.0362P)2 + 1.6163P]
where P = (Fo2 + 2Fc2)/3
2327 reflections(Δ/σ)max = 0.002
192 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.34 e Å3
Crystal data top
C22H30ClO4PSV = 2360.3 (4) Å3
Mr = 456.94Z = 4
Monoclinic, C2/cMo Kα radiation
a = 23.592 (3) ŵ = 0.34 mm1
b = 8.3111 (6) ÅT = 150 K
c = 12.5067 (14) Å0.64 × 0.59 × 0.55 mm
β = 105.740 (9)°
Data collection top
Stoe IPDS-II
diffractometer
2327 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
2146 reflections with I > 2σ(I)
Tmin = 0.824, Tmax = 0.869Rint = 0.032
16485 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.073All H-atom parameters refined
S = 1.08Δρmax = 0.17 e Å3
2327 reflectionsΔρmin = 0.34 e Å3
192 parameters
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*/UeqOcc. (<1)
C10.58872 (5)0.29212 (15)0.41994 (10)0.0224 (3)
C20.59796 (6)0.14466 (16)0.47516 (11)0.0258 (3)
C30.65010 (6)0.11722 (16)0.55649 (11)0.0272 (3)
C40.69210 (5)0.23993 (16)0.58337 (10)0.0249 (3)
C50.68201 (6)0.38769 (16)0.52737 (11)0.0252 (3)
C60.62988 (5)0.41888 (15)0.44326 (10)0.0233 (3)
C70.61903 (6)0.58369 (16)0.38318 (12)0.0296 (3)
C80.61032 (8)0.56105 (19)0.25687 (13)0.0374 (3)
C90.56458 (8)0.66639 (19)0.40646 (15)0.0402 (4)
C100.67218 (8)0.6983 (2)0.42394 (16)0.0453 (4)
C110.78481 (6)0.32952 (19)0.70159 (13)0.0343 (3)
O10.53449 (4)0.31975 (10)0.33826 (7)0.0257 (2)
O20.74184 (4)0.20383 (12)0.66690 (8)0.0319 (2)
P10.50000.19428 (5)0.25000.02610 (13)
Cl10.554354 (14)0.06331 (4)0.18992 (3)0.03162 (11)0.50
S10.554354 (14)0.06331 (4)0.18992 (3)0.03162 (11)0.50
H20.5683 (7)0.0634 (19)0.4571 (13)0.032 (4)*
H30.6579 (7)0.014 (2)0.5947 (13)0.034 (4)*
H50.7120 (7)0.4671 (19)0.5482 (13)0.029 (4)*
H8A0.6047 (8)0.668 (3)0.2193 (16)0.052 (5)*
H8B0.5774 (8)0.495 (2)0.2241 (15)0.043 (5)*
H8C0.6466 (9)0.512 (2)0.2429 (17)0.056 (5)*
H9A0.5571 (8)0.772 (2)0.3671 (15)0.051 (5)*
H9B0.5703 (8)0.686 (2)0.4892 (18)0.056 (5)*
H9C0.5281 (8)0.601 (2)0.3804 (15)0.047 (5)*
H10A0.7097 (9)0.650 (2)0.4105 (16)0.056 (6)*
H10B0.6816 (9)0.720 (2)0.5075 (19)0.059 (6)*
H10C0.6631 (9)0.798 (2)0.3852 (17)0.056 (5)*
H11A0.8030 (8)0.360 (2)0.6410 (15)0.042 (5)*
H11B0.8151 (8)0.282 (2)0.7644 (15)0.041 (4)*
H11C0.7671 (7)0.427 (2)0.7281 (14)0.035 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0207 (6)0.0240 (6)0.0204 (6)0.0000 (5)0.0020 (4)0.0009 (5)
C20.0254 (6)0.0247 (6)0.0254 (6)0.0045 (5)0.0037 (5)0.0004 (5)
C30.0293 (7)0.0261 (7)0.0243 (6)0.0001 (5)0.0037 (5)0.0030 (5)
C40.0223 (6)0.0311 (7)0.0198 (6)0.0006 (5)0.0029 (5)0.0023 (5)
C50.0241 (6)0.0262 (6)0.0246 (6)0.0044 (5)0.0053 (5)0.0041 (5)
C60.0253 (6)0.0223 (6)0.0222 (6)0.0015 (5)0.0064 (5)0.0023 (5)
C70.0315 (7)0.0212 (6)0.0333 (7)0.0037 (5)0.0041 (6)0.0019 (5)
C80.0447 (9)0.0336 (8)0.0327 (8)0.0051 (7)0.0086 (7)0.0086 (6)
C90.0443 (9)0.0242 (7)0.0498 (10)0.0051 (6)0.0087 (7)0.0019 (7)
C100.0439 (9)0.0279 (8)0.0556 (11)0.0124 (7)0.0012 (8)0.0062 (7)
C110.0253 (7)0.0395 (8)0.0322 (7)0.0019 (6)0.0021 (6)0.0082 (6)
O10.0238 (4)0.0220 (4)0.0260 (5)0.0002 (3)0.0022 (4)0.0019 (4)
O20.0252 (5)0.0360 (5)0.0283 (5)0.0015 (4)0.0033 (4)0.0005 (4)
P10.0288 (2)0.0192 (2)0.0242 (2)0.0000.00339 (18)0.000
Cl10.02605 (18)0.0368 (2)0.0320 (2)0.00652 (13)0.00781 (14)0.00242 (13)
S10.02605 (18)0.0368 (2)0.0320 (2)0.00652 (13)0.00781 (14)0.00242 (13)
Geometric parameters (Å, º) top
C1—C21.3946 (18)C8—H8C1.00 (2)
C1—C61.4086 (17)C9—H9A1.00 (2)
C1—O11.4226 (14)C9—H9B1.02 (2)
C2—C31.3860 (18)C9—H9C0.994 (19)
C2—H20.955 (16)C10—H10A1.03 (2)
C3—C41.3979 (18)C10—H10B1.02 (2)
C3—H30.974 (17)C10—H10C0.96 (2)
C4—O21.3759 (15)C11—O21.4383 (17)
C4—C51.4017 (19)C11—H11A0.998 (18)
C5—C61.4088 (18)C11—H11B0.990 (18)
C5—H50.952 (16)C11—H11C1.009 (17)
C6—C71.5499 (18)O1—P11.5750 (9)
C7—C101.5468 (19)P1—O1i1.5750 (9)
C7—C81.548 (2)P1—S1i1.9791 (4)
C7—C91.552 (2)P1—Cl1i1.9791 (4)
C8—H8A1.00 (2)P1—Cl11.9791 (4)
C8—H8B0.948 (19)
C2—C1—C6123.25 (11)C7—C9—H9A109.9 (11)
C2—C1—O1119.13 (11)C7—C9—H9B111.8 (11)
C6—C1—O1117.58 (11)H9A—C9—H9B108.6 (16)
C3—C2—C1119.77 (12)C7—C9—H9C112.5 (11)
C3—C2—H2120.3 (9)H9A—C9—H9C107.2 (15)
C1—C2—H2119.9 (9)H9B—C9—H9C106.6 (15)
C2—C3—C4119.11 (12)C7—C10—H10A111.4 (11)
C2—C3—H3121.1 (9)C7—C10—H10B112.1 (11)
C4—C3—H3119.8 (9)H10A—C10—H10B106.1 (16)
O2—C4—C3115.24 (12)C7—C10—H10C108.5 (12)
O2—C4—C5124.38 (11)H10A—C10—H10C109.9 (16)
C3—C4—C5120.39 (11)H10B—C10—H10C108.8 (16)
C4—C5—C6121.99 (12)O2—C11—H11A111.5 (10)
C4—C5—H5117.3 (9)O2—C11—H11B104.1 (10)
C6—C5—H5120.7 (9)H11A—C11—H11B109.7 (14)
C1—C6—C5115.48 (11)O2—C11—H11C111.3 (9)
C1—C6—C7123.14 (11)H11A—C11—H11C110.4 (14)
C5—C6—C7121.37 (11)H11B—C11—H11C109.7 (13)
C10—C7—C8106.40 (13)C1—O1—P1126.11 (8)
C10—C7—C6111.83 (11)C4—O2—C11117.18 (11)
C8—C7—C6110.24 (11)O1—P1—O1i97.08 (7)
C10—C7—C9107.68 (13)O1—P1—S1i111.27 (4)
C8—C7—C9110.96 (12)O1i—P1—S1i111.44 (3)
C6—C7—C9109.67 (12)O1—P1—Cl1i111.27 (4)
C7—C8—H8A109.7 (11)O1i—P1—Cl1i111.44 (3)
C7—C8—H8B112.2 (11)S1i—P1—Cl1i0.00 (2)
H8A—C8—H8B108.9 (16)O1—P1—Cl1111.44 (3)
C7—C8—H8C110.0 (12)O1i—P1—Cl1111.27 (4)
H8A—C8—H8C106.8 (16)S1i—P1—Cl1113.26 (3)
H8B—C8—H8C109.0 (16)Cl1i—P1—Cl1113.26 (3)
C6—C1—C2—C30.8 (2)C5—C6—C7—C102.35 (18)
O1—C1—C2—C3178.73 (11)C1—C6—C7—C860.70 (16)
C1—C2—C3—C41.4 (2)C5—C6—C7—C8120.51 (13)
C2—C3—C4—O2178.39 (11)C1—C6—C7—C961.76 (16)
C2—C3—C4—C51.14 (19)C5—C6—C7—C9117.03 (14)
O2—C4—C5—C6179.21 (11)C2—C1—O1—P140.07 (15)
C3—C4—C5—C60.28 (19)C6—C1—O1—P1141.89 (10)
C2—C1—C6—C50.05 (18)C3—C4—O2—C11176.65 (12)
O1—C1—C6—C5177.90 (10)C5—C4—O2—C112.86 (18)
C2—C1—C6—C7178.90 (12)C1—O1—P1—O1i155.66 (11)
O1—C1—C6—C70.95 (18)C1—O1—P1—S1i88.01 (9)
C4—C5—C6—C10.31 (18)C1—O1—P1—Cl1i88.01 (9)
C4—C5—C6—C7179.19 (12)C1—O1—P1—Cl139.46 (10)
C1—C6—C7—C10178.86 (13)
Symmetry code: (i) x+1, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC22H30ClO4PS
Mr456.94
Crystal system, space groupMonoclinic, C2/c
Temperature (K)150
a, b, c (Å)23.592 (3), 8.3111 (6), 12.5067 (14)
β (°) 105.740 (9)
V3)2360.3 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.34
Crystal size (mm)0.64 × 0.59 × 0.55
Data collection
DiffractometerStoe IPDS-II
diffractometer
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.824, 0.869
No. of measured, independent and
observed [I > 2σ(I)] reflections
16485, 2327, 2146
Rint0.032
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.073, 1.08
No. of reflections2327
No. of parameters192
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.17, 0.34

Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
C1—C21.3946 (18)C4—C51.4017 (19)
C1—C61.4086 (17)C5—C61.4088 (18)
C1—O11.4226 (14)O1—P11.5750 (9)
C2—C31.3860 (18)P1—S1i1.9791 (4)
C3—C41.3979 (18)P1—Cl11.9791 (4)
C2—C1—C6123.25 (11)C4—C5—C6121.99 (12)
C2—C1—O1119.13 (11)C1—C6—C5115.48 (11)
C6—C1—O1117.58 (11)O1—P1—O1i97.08 (7)
C3—C2—C1119.77 (12)O1—P1—S1i111.27 (4)
C2—C3—C4119.11 (12)O1—P1—Cl1111.44 (3)
C3—C4—C5120.39 (11)S1i—P1—Cl1113.26 (3)
Symmetry code: (i) x+1, y, z+1/2.
 

References

First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
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First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
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