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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o391.
Published online 2009 January 28. doi:  10.1107/S160053680900258X
PMCID: PMC2968383

2-(4-Hydroxy­phenyl­sulfon­yl)phenol

Abstract

The title compound, C12H10O4S, is a phenolic color developer used for leuco colorants. The two benzene rings with substituent hydr­oxy groups are nearly perpendicular to each other [dihedral angle = 91.5 (1)°]. There are inter­molecular O—H(...)O hydrogen bonds between an OH group of one mol­ecule and a sulfonyl O atom of a neighboring mol­ecule. One mol­ecule is hydrogen bonded to four symmetry-related mol­ecules, forming a two-dimensional hydrogen-bond network.

Related literature

For general background literature on leuco dyes, see: Muthyala (1997 [triangle]). For the structure of 4,4′-sulfonyl­diphenol, see: Glidewell & Ferguson (1996 [triangle]); Davies et al. (1997 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o391-scheme1.jpg

Experimental

Crystal data

  • C12H10O4S
  • M r = 250.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o391-efi1.jpg
  • a = 10.9525 (2) Å
  • b = 14.4404 (3) Å
  • c = 7.0361 (1) Å
  • β = 93.8147 (10)°
  • V = 1110.35 (3) Å3
  • Z = 4
  • Cu- Kα radiation
  • μ = 2.62 mm−1
  • T = 93.1 K
  • 0.39 × 0.35 × 0.29 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.408, T max = 0.468
  • 9436 measured reflections
  • 1998 independent reflections
  • 1830 reflections with F 2 > 2σ(F 2)
  • R int = 0.154

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.162
  • S = 1.10
  • 1998 reflections
  • 163 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.55 e Å−3
  • Δρmin = −0.66 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 [triangle]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2006 [triangle]); program(s) used to solve structure: SIR2004 (Burla et al., 2005 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 [triangle]); software used to prepare material for publication: CrystalStructure.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900258X/bh2215sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900258X/bh2215Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

The colorless leuco dye is known to exhibit a brilliant color when the lactone-ring is opened by the formation of intermolecular hydrogen bonds between dye and developer, and is used in practice in thermal or rewritable papers (Muthyala, 1997). The title compound has found use as a developer for fluoran leuco dyes which give a black color. Since the color is generated by a solid state reaction by heating a mixture of dye and developer particles, the mutual geometrical relation of dye and developer molecules plays an important role in color strength in the solid state. For this reason, structure analysis of 2-[4-hydroxyphenyl]sulfonyl]-phenol, (I), has been carried out in the present investigation.

Figure 1 shows the ORTEPIII plot (Burnett & Johnson, 1996) of (I). The two benzene rings with 2-hydroxy or 4-hydroxy group are nearly perpendicular to each other [dihedral angle: 91.5 (1)°]. Figure 2 is the projection of the crystal structure onto the (b,c) plane. There are O—H···O intermolecular hydrogen bonds between the OH of one molecule and the sulfonyl O atom of the neighboring one along the b and c axes. One molecule is hydrogen-bonded to four different molecules, forming a two-dimensional hydrogen-bond network. A similar two-dimensional network is found in 4,4'-sulfonyldiphenol (Glidewell & Ferguson, 1996; Davies et al., 1997).

Experimental

Compound (I) was obtained from Mitsubisihi Paper Mills., Ltd., and was recrystallized from an ethanol solution. After 48 h., a number of colorless crystals were obtained in the form of blocks.

Refinement

The H atoms of the hydroxy groups (H3O and H4O) were found in density maps and refined isotropically. All other H atoms were positioned geometrically and included in the riding-model approximation, with C—H distances of 0.95 Å, and Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
A view of the molecular structure of (I), showing 50% probability displacement ellipsoids for non-H atoms.
Fig. 2.
Projection of the structure of (I) onto the b and c plane, showing O—H···O intermolecular hydrogen bonds in dotted lines. One molecule is hydrogen-bonded to four different molecules along the b and c axes.

Crystal data

C12H10O4SF(000) = 520.00
Mr = 250.27Dx = 1.497 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ybcCell parameters from 9882 reflections
a = 10.9525 (2) Åθ = 3.1–68.2°
b = 14.4404 (3) ŵ = 2.62 mm1
c = 7.0361 (1) ÅT = 93 K
β = 93.8147 (10)°Block, colorless
V = 1110.35 (3) Å30.39 × 0.35 × 0.29 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer1830 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.154
ω scansθmax = 68.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −12→12
Tmin = 0.408, Tmax = 0.468k = −17→17
9436 measured reflectionsl = −8→8
1998 independent reflections

Refinement

Refinement on F2H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.058w = 1/[σ2(Fo2) + (0.078P)2 + 1.2611P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.162(Δ/σ)max < 0.001
S = 1.10Δρmax = 0.55 e Å3
1998 reflectionsΔρmin = −0.66 e Å3
163 parametersExtinction correction: SHELXL97 (Sheldrick, 2008)
0 restraintsExtinction coefficient: 0.0078 (10)
0 constraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.27104 (6)0.93583 (5)0.66743 (9)0.0192 (2)
O10.30244 (18)1.03113 (13)0.7107 (3)0.0240 (5)
O20.23614 (19)0.91341 (15)0.4710 (2)0.0272 (5)
O30.25813 (18)0.94202 (14)1.0879 (2)0.0217 (4)
O40.70235 (18)0.71229 (14)0.9019 (3)0.0253 (5)
C10.1463 (2)0.90270 (18)0.7994 (3)0.0184 (5)
C20.1531 (2)0.91128 (18)0.9972 (4)0.0201 (6)
C30.0508 (2)0.8876 (2)1.0952 (4)0.0222 (6)
C4−0.0549 (2)0.8560 (2)0.9967 (4)0.0243 (6)
C5−0.0613 (2)0.8473 (2)0.7997 (4)0.0265 (6)
C60.0399 (2)0.8704 (2)0.7008 (4)0.0243 (6)
C70.3959 (2)0.86727 (19)0.7456 (3)0.0192 (5)
C80.5037 (2)0.90989 (19)0.8143 (4)0.0209 (6)
C90.6055 (2)0.85644 (19)0.8666 (4)0.0218 (6)
C100.5990 (2)0.76019 (19)0.8485 (3)0.0199 (6)
C110.4904 (2)0.71764 (18)0.7819 (3)0.0204 (6)
C120.3887 (2)0.77072 (19)0.7286 (3)0.0213 (6)
H3O0.257 (3)0.940 (2)1.212 (5)0.023 (8)*
H4O0.695 (4)0.653 (3)0.862 (6)0.058 (12)*
H30.05350.89331.23000.025*
H4−0.12370.83951.06530.027*
H5−0.13410.82550.73180.028*
H60.03690.86440.56640.027*
H80.50710.97550.82640.022*
H90.67920.88510.91430.025*
H110.48650.65180.77200.023*
H120.31430.74220.68130.024*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0162 (4)0.0227 (4)0.0174 (4)−0.0020 (2)−0.0079 (2)0.0010 (2)
O10.0209 (10)0.0219 (10)0.0280 (10)−0.0042 (7)−0.0088 (8)0.0019 (8)
O20.0222 (11)0.0383 (11)0.0199 (10)−0.0033 (8)−0.0087 (8)0.0052 (9)
O30.0172 (10)0.0281 (10)0.0185 (10)−0.0040 (7)−0.0089 (8)0.0000 (8)
O40.0167 (10)0.0220 (10)0.0359 (11)0.0023 (7)−0.0089 (8)−0.0010 (9)
C10.0140 (12)0.0198 (12)0.0206 (13)−0.0011 (9)−0.0050 (10)0.0013 (11)
C20.0167 (13)0.0180 (12)0.0240 (14)0.0030 (10)−0.0100 (10)0.0040 (11)
C30.0193 (13)0.0265 (13)0.0197 (13)0.0024 (10)−0.0071 (10)0.0018 (11)
C40.0169 (13)0.0278 (14)0.0273 (15)−0.0001 (10)−0.0056 (10)0.0028 (12)
C50.0186 (14)0.0295 (15)0.0295 (15)−0.0054 (11)−0.0123 (11)−0.0008 (12)
C60.0211 (14)0.0299 (14)0.0204 (13)−0.0023 (11)−0.0091 (10)−0.0026 (12)
C70.0172 (13)0.0230 (13)0.0160 (12)−0.0017 (10)−0.0081 (10)0.0002 (11)
C80.0190 (14)0.0189 (12)0.0240 (14)−0.0028 (10)−0.0039 (10)−0.0024 (11)
C90.0188 (14)0.0204 (13)0.0251 (14)−0.0042 (10)−0.0064 (10)−0.0032 (11)
C100.0191 (13)0.0213 (13)0.0186 (12)−0.0001 (10)−0.0049 (10)−0.0026 (11)
C110.0216 (14)0.0181 (12)0.0206 (13)−0.0031 (10)−0.0050 (10)−0.0032 (10)
C120.0206 (13)0.0222 (13)0.0201 (13)−0.0057 (10)−0.0063 (10)−0.0024 (11)

Geometric parameters (Å, °)

S1—O11.446 (2)C4—H40.952
S1—O21.446 (2)C5—C61.388 (4)
S1—C11.768 (2)C5—H50.955
S1—C71.747 (2)C6—H60.948
O3—C21.353 (3)C7—C81.389 (3)
O3—H3O0.87 (3)C7—C121.401 (3)
O4—C101.358 (3)C8—C91.386 (3)
O4—H4O0.90 (4)C8—H80.951
C1—C21.395 (3)C9—C101.397 (3)
C1—C61.396 (3)C9—H90.948
C2—C31.397 (4)C10—C111.392 (3)
C3—C41.386 (3)C11—C121.383 (3)
C3—H30.950C11—H110.953
C4—C51.389 (4)C12—H120.953
O1···O4i2.733 (2)O3···H8ii2.862
O1···H4Oi1.84 (4)O3···H9ii2.590
O1···H9ii2.898O3···H12v2.799
O1···H11i2.891O4···O1vi2.733 (2)
O2···O3iii2.753 (2)O4···H4vii2.835
O2···H3Oiii1.89 (3)O4···H5vii2.757
O2···H3iii2.552O4···H5viii2.888
O3···O2iv2.753 (2)C4···H9ix2.962
O1—S1—O2117.29 (12)C6—C5—H5119.7
O1—S1—C1109.16 (12)C1—C6—C5119.9 (2)
O1—S1—C7107.63 (12)C1—C6—H6119.9
O2—S1—C1106.08 (12)C5—C6—H6120.2
O2—S1—C7108.99 (12)S1—C7—C8119.2 (2)
C1—S1—C7107.30 (12)S1—C7—C12119.9 (2)
C2—O3—H3O113 (2)C8—C7—C12120.8 (2)
C10—O4—H4O110 (2)C7—C8—C9119.7 (2)
S1—C1—C2120.6 (2)C7—C8—H8120.0
S1—C1—C6118.6 (2)C9—C8—H8120.3
C2—C1—C6120.9 (2)C8—C9—C10119.6 (2)
O3—C2—C1119.1 (2)C8—C9—H9120.1
O3—C2—C3122.2 (2)C10—C9—H9120.2
C1—C2—C3118.7 (2)O4—C10—C9116.4 (2)
C2—C3—C4120.3 (2)O4—C10—C11123.1 (2)
C2—C3—H3119.9C9—C10—C11120.5 (2)
C4—C3—H3119.8C10—C11—C12120.1 (2)
C3—C4—C5120.9 (2)C10—C11—H11119.8
C3—C4—H4119.4C12—C11—H11120.1
C5—C4—H4119.6C7—C12—C11119.3 (2)
C4—C5—C6119.3 (2)C7—C12—H12120.1
C4—C5—H5120.9C11—C12—H12120.6
O1—S1—C1—C2−55.8 (2)C6—C1—C2—C3−0.5 (3)
O1—S1—C1—C6122.4 (2)O3—C2—C3—C4−179.7 (2)
O1—S1—C7—C8−6.2 (2)C1—C2—C3—C40.1 (3)
O1—S1—C7—C12177.4 (2)C2—C3—C4—C50.0 (3)
O2—S1—C1—C2177.0 (2)C3—C4—C5—C60.1 (3)
O2—S1—C1—C6−4.9 (2)C4—C5—C6—C1−0.4 (4)
O2—S1—C7—C8122.0 (2)S1—C7—C8—C9−176.4 (2)
O2—S1—C7—C12−54.5 (2)S1—C7—C12—C11176.7 (2)
C1—S1—C7—C8−123.5 (2)C8—C7—C12—C110.3 (4)
C1—S1—C7—C1260.0 (2)C12—C7—C8—C90.1 (3)
C7—S1—C1—C260.6 (2)C7—C8—C9—C100.4 (4)
C7—S1—C1—C6−121.3 (2)C8—C9—C10—O4179.8 (2)
S1—C1—C2—O3−2.5 (3)C8—C9—C10—C11−1.3 (4)
S1—C1—C2—C3177.6 (2)O4—C10—C11—C12−179.6 (2)
S1—C1—C6—C5−177.5 (2)C9—C10—C11—C121.6 (4)
C2—C1—C6—C50.6 (4)C10—C11—C12—C7−1.1 (4)
C6—C1—C2—O3179.4 (2)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, −y+2, −z+2; (iii) x, y, z−1; (iv) x, y, z+1; (v) x, −y+3/2, z+1/2; (vi) −x+1, y−1/2, −z+3/2; (vii) x+1, y, z; (viii) x+1, −y+3/2, z+1/2; (ix) x−1, y, z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3O···O2iv0.87 (3)1.90 (3)2.753 (2)168 (3)
O4—H4O···O1vi0.88 (4)1.85 (4)2.733 (2)173 (3)

Symmetry codes: (iv) x, y, z+1; (vi) −x+1, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2215).

References

  • Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst.38, 381–388.
  • Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
  • Davies, C., Langler, R. F., Sharma, C. V. K. & Zaworotko, M. J. (1997). Chem. Commun. pp. 567–568.
  • Glidewell, C. & Ferguson, G. (1996). Acta Cryst. C52, 2528–2530.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Muthyala, R. (1997). In Chemistry and Applications of Leuco Dyes New York, London: Plenum Press.
  • Rigaku (1998). PROCESS-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2006). CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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