2-(4-Hydroxy­phenyl­sulfon­yl)phenol

Sato, K.; Shima, H.; Mizuguchi, J.

doi:10.1107/S160053680900258X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o391

doi:10.1107/S160053680900258X

Open

access

2-(4-Hydroxyphenylsulfonyl)phenol

Kazuyuki Sato,^a Hideki Shima ^a and Jin Mizuguchi ^a ^*

^aDepartment of Applied Physics, Graduate School of Engineering, Yokohama National University, 79-5 Tokiwadai, Hodogaya-ku, 240-8501 Yokohama, Japan
^*Correspondence e-mail: mizu-j@ynu.ac.jp

(Received 30 December 2008; accepted 21 January 2009; online 28 January 2009)

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 ). For the structure of 4,4′-sulfonyldiphenol, see: Glidewell & Ferguson (1996 ); Davies et al. (1997 ).

Experimental

Crystal data

C₁₂H₁₀O₄S
M_r = 250.27
Monoclinic, P 2₁ /c
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 ) T_min = 0.408, T_max = 0.468
9436 measured reflections
1998 independent reflections
1830 reflections with F² > 2σ(F²)
R_int = 0.154

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.162
S = 1.10
1998 reflections
163 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O2ⁱ	0.87 (3)	1.90 (3)	2.753 (2)	168 (3)
O4—H4O⋯O1ⁱⁱ	0.88 (4)	1.85 (4)	2.733 (2)	173 (3)
Symmetry codes: (i) x, y, z+1; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

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

Figures top

	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.

2-(4-Hydroxyphenylsulfonyl)phenol top

Crystal data top

C₁₂H₁₀O₄S	F(000) = 520.00
M_r = 250.27	D_x = 1.497 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ybc	Cell parameters from 9882 reflections
a = 10.9525 (2) Å	θ = 3.1–68.2°
b = 14.4404 (3) Å	µ = 2.62 mm⁻¹
c = 7.0361 (1) Å	T = 93 K
β = 93.8147 (10)°	Block, colorless
V = 1110.35 (3) Å³	0.39 × 0.35 × 0.29 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	1830 reflections with F² > 2σ(F²)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.154
ω scans	θ_max = 68.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
T_min = 0.408, T_max = 0.468	k = −17→17
9436 measured reflections	l = −8→8
1998 independent reflections

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.058	w = 1/[σ²(F_o²) + (0.078P)² + 1.2611P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.162	(Δ/σ)_max < 0.001
S = 1.10	Δρ_max = 0.55 e Å⁻³
1998 reflections	Δρ_min = −0.66 e Å⁻³
163 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008)
0 restraints	Extinction coefficient: 0.0078 (10)
0 constraints

Crystal data top

C₁₂H₁₀O₄S	V = 1110.35 (3) Å³
M_r = 250.27	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 10.9525 (2) Å	µ = 2.62 mm⁻¹
b = 14.4404 (3) Å	T = 93 K
c = 7.0361 (1) Å	0.39 × 0.35 × 0.29 mm
β = 93.8147 (10)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	1998 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1830 reflections with F² > 2σ(F²)
T_min = 0.408, T_max = 0.468	R_int = 0.154
9436 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.162	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.55 e Å⁻³
1998 reflections	Δρ_min = −0.66 e Å⁻³
163 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.27104 (6)	0.93583 (5)	0.66743 (9)	0.0192 (2)
O1	0.30244 (18)	1.03113 (13)	0.7107 (3)	0.0240 (5)
O2	0.23614 (19)	0.91341 (15)	0.4710 (2)	0.0272 (5)
O3	0.25813 (18)	0.94202 (14)	1.0879 (2)	0.0217 (4)
O4	0.70235 (18)	0.71229 (14)	0.9019 (3)	0.0253 (5)
C1	0.1463 (2)	0.90270 (18)	0.7994 (3)	0.0184 (5)
C2	0.1531 (2)	0.91128 (18)	0.9972 (4)	0.0201 (6)
C3	0.0508 (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)
C6	0.0399 (2)	0.8704 (2)	0.7008 (4)	0.0243 (6)
C7	0.3959 (2)	0.86727 (19)	0.7456 (3)	0.0192 (5)
C8	0.5037 (2)	0.90989 (19)	0.8143 (4)	0.0209 (6)
C9	0.6055 (2)	0.85644 (19)	0.8666 (4)	0.0218 (6)
C10	0.5990 (2)	0.76019 (19)	0.8485 (3)	0.0199 (6)
C11	0.4904 (2)	0.71764 (18)	0.7819 (3)	0.0204 (6)
C12	0.3887 (2)	0.77072 (19)	0.7286 (3)	0.0213 (6)
H3O	0.257 (3)	0.940 (2)	1.212 (5)	0.023 (8)*
H4O	0.695 (4)	0.653 (3)	0.862 (6)	0.058 (12)*
H3	0.0535	0.8933	1.2300	0.025*
H4	−0.1237	0.8395	1.0653	0.027*
H5	−0.1341	0.8255	0.7318	0.028*
H6	0.0369	0.8644	0.5664	0.027*
H8	0.5071	0.9755	0.8264	0.022*
H9	0.6792	0.8851	0.9143	0.025*
H11	0.4865	0.6518	0.7720	0.023*
H12	0.3143	0.7422	0.6813	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0162 (4)	0.0227 (4)	0.0174 (4)	−0.0020 (2)	−0.0079 (2)	0.0010 (2)
O1	0.0209 (10)	0.0219 (10)	0.0280 (10)	−0.0042 (7)	−0.0088 (8)	0.0019 (8)
O2	0.0222 (11)	0.0383 (11)	0.0199 (10)	−0.0033 (8)	−0.0087 (8)	0.0052 (9)
O3	0.0172 (10)	0.0281 (10)	0.0185 (10)	−0.0040 (7)	−0.0089 (8)	−0.0000 (8)
O4	0.0167 (10)	0.0220 (10)	0.0359 (11)	0.0023 (7)	−0.0089 (8)	−0.0010 (9)
C1	0.0140 (12)	0.0198 (12)	0.0206 (13)	−0.0011 (9)	−0.0050 (10)	0.0013 (11)
C2	0.0167 (13)	0.0180 (12)	0.0240 (14)	0.0030 (10)	−0.0100 (10)	0.0040 (11)
C3	0.0193 (13)	0.0265 (13)	0.0197 (13)	0.0024 (10)	−0.0071 (10)	0.0018 (11)
C4	0.0169 (13)	0.0278 (14)	0.0273 (15)	−0.0001 (10)	−0.0056 (10)	0.0028 (12)
C5	0.0186 (14)	0.0295 (15)	0.0295 (15)	−0.0054 (11)	−0.0123 (11)	−0.0008 (12)
C6	0.0211 (14)	0.0299 (14)	0.0204 (13)	−0.0023 (11)	−0.0091 (10)	−0.0026 (12)
C7	0.0172 (13)	0.0230 (13)	0.0160 (12)	−0.0017 (10)	−0.0081 (10)	0.0002 (11)
C8	0.0190 (14)	0.0189 (12)	0.0240 (14)	−0.0028 (10)	−0.0039 (10)	−0.0024 (11)
C9	0.0188 (14)	0.0204 (13)	0.0251 (14)	−0.0042 (10)	−0.0064 (10)	−0.0032 (11)
C10	0.0191 (13)	0.0213 (13)	0.0186 (12)	−0.0001 (10)	−0.0049 (10)	−0.0026 (11)
C11	0.0216 (14)	0.0181 (12)	0.0206 (13)	−0.0031 (10)	−0.0050 (10)	−0.0032 (10)
C12	0.0206 (13)	0.0222 (13)	0.0201 (13)	−0.0057 (10)	−0.0063 (10)	−0.0024 (11)

Geometric parameters (Å, º) top

S1—O1	1.446 (2)	C4—H4	0.952
S1—O2	1.446 (2)	C5—C6	1.388 (4)
S1—C1	1.768 (2)	C5—H5	0.955
S1—C7	1.747 (2)	C6—H6	0.948
O3—C2	1.353 (3)	C7—C8	1.389 (3)
O3—H3O	0.87 (3)	C7—C12	1.401 (3)
O4—C10	1.358 (3)	C8—C9	1.386 (3)
O4—H4O	0.90 (4)	C8—H8	0.951
C1—C2	1.395 (3)	C9—C10	1.397 (3)
C1—C6	1.396 (3)	C9—H9	0.948
C2—C3	1.397 (4)	C10—C11	1.392 (3)
C3—C4	1.386 (3)	C11—C12	1.383 (3)
C3—H3	0.950	C11—H11	0.953
C4—C5	1.389 (4)	C12—H12	0.953

O1···O4ⁱ	2.733 (2)	O3···H8ⁱⁱ	2.862
O1···H4Oⁱ	1.84 (4)	O3···H9ⁱⁱ	2.590
O1···H9ⁱⁱ	2.898	O3···H12^v	2.799
O1···H11ⁱ	2.891	O4···O1^vi	2.733 (2)
O2···O3ⁱⁱⁱ	2.753 (2)	O4···H4^vii	2.835
O2···H3Oⁱⁱⁱ	1.89 (3)	O4···H5^vii	2.757
O2···H3ⁱⁱⁱ	2.552	O4···H5^viii	2.888
O3···O2^iv	2.753 (2)	C4···H9^ix	2.962

O1—S1—O2	117.29 (12)	C6—C5—H5	119.7
O1—S1—C1	109.16 (12)	C1—C6—C5	119.9 (2)
O1—S1—C7	107.63 (12)	C1—C6—H6	119.9
O2—S1—C1	106.08 (12)	C5—C6—H6	120.2
O2—S1—C7	108.99 (12)	S1—C7—C8	119.2 (2)
C1—S1—C7	107.30 (12)	S1—C7—C12	119.9 (2)
C2—O3—H3O	113 (2)	C8—C7—C12	120.8 (2)
C10—O4—H4O	110 (2)	C7—C8—C9	119.7 (2)
S1—C1—C2	120.6 (2)	C7—C8—H8	120.0
S1—C1—C6	118.6 (2)	C9—C8—H8	120.3
C2—C1—C6	120.9 (2)	C8—C9—C10	119.6 (2)
O3—C2—C1	119.1 (2)	C8—C9—H9	120.1
O3—C2—C3	122.2 (2)	C10—C9—H9	120.2
C1—C2—C3	118.7 (2)	O4—C10—C9	116.4 (2)
C2—C3—C4	120.3 (2)	O4—C10—C11	123.1 (2)
C2—C3—H3	119.9	C9—C10—C11	120.5 (2)
C4—C3—H3	119.8	C10—C11—C12	120.1 (2)
C3—C4—C5	120.9 (2)	C10—C11—H11	119.8
C3—C4—H4	119.4	C12—C11—H11	120.1
C5—C4—H4	119.6	C7—C12—C11	119.3 (2)
C4—C5—C6	119.3 (2)	C7—C12—H12	120.1
C4—C5—H5	120.9	C11—C12—H12	120.6

O1—S1—C1—C2	−55.8 (2)	C6—C1—C2—C3	−0.5 (3)
O1—S1—C1—C6	122.4 (2)	O3—C2—C3—C4	−179.7 (2)
O1—S1—C7—C8	−6.2 (2)	C1—C2—C3—C4	0.1 (3)
O1—S1—C7—C12	177.4 (2)	C2—C3—C4—C5	0.0 (3)
O2—S1—C1—C2	177.0 (2)	C3—C4—C5—C6	0.1 (3)
O2—S1—C1—C6	−4.9 (2)	C4—C5—C6—C1	−0.4 (4)
O2—S1—C7—C8	122.0 (2)	S1—C7—C8—C9	−176.4 (2)
O2—S1—C7—C12	−54.5 (2)	S1—C7—C12—C11	176.7 (2)
C1—S1—C7—C8	−123.5 (2)	C8—C7—C12—C11	0.3 (4)
C1—S1—C7—C12	60.0 (2)	C12—C7—C8—C9	0.1 (3)
C7—S1—C1—C2	60.6 (2)	C7—C8—C9—C10	0.4 (4)
C7—S1—C1—C6	−121.3 (2)	C8—C9—C10—O4	179.8 (2)
S1—C1—C2—O3	−2.5 (3)	C8—C9—C10—C11	−1.3 (4)
S1—C1—C2—C3	177.6 (2)	O4—C10—C11—C12	−179.6 (2)
S1—C1—C6—C5	−177.5 (2)	C9—C10—C11—C12	1.6 (4)
C2—C1—C6—C5	0.6 (4)	C10—C11—C12—C7	−1.1 (4)
C6—C1—C2—O3	179.4 (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, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2^iv	0.87 (3)	1.90 (3)	2.753 (2)	168 (3)
O4—H4O···O1^vi	0.88 (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.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀O₄S
M_r	250.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	93
a, b, c (Å)	10.9525 (2), 14.4404 (3), 7.0361 (1)
β (°)	93.8147 (10)
V (Å³)	1110.35 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.62
Crystal size (mm)	0.39 × 0.35 × 0.29

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.408, 0.468
No. of measured, independent and observed [F² > 2σ(F²)] reflections	9436, 1998, 1830
R_int	0.154
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.162, 1.10
No. of reflections	1998
No. of parameters	163
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.66

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2006), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2ⁱ	0.87 (3)	1.90 (3)	2.753 (2)	168 (3)
O4—H4O···O1ⁱⁱ	0.88 (4)	1.85 (4)	2.733 (2)	173 (3)

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

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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Davies, C., Langler, R. F., Sharma, C. V. K. & Zaworotko, M. J. (1997). Chem. Commun. pp. 567–568. CSD CrossRef Web of Science Google Scholar
Glidewell, C. & Ferguson, G. (1996). Acta Cryst. C52, 2528–2530. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Muthyala, R. (1997). In Chemistry and Applications of Leuco Dyes. New York, London: Plenum Press. Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2006). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o391

doi:10.1107/S160053680900258X

Open

access