2-[(2-Carboxy-phen-yl)disulfan-yl]benzoic acid-4,4'-bipyridyl N,N'-dioxide (1/2).

In the title 2:1 adduct, C(14)H(10)O(4)S(2)·0.5C(10)H(8)N(2)O(2), which arose from an unexpected oxidation of a precursor, the dihedral angle between the aromatic rings in the disulfide is 82.51 (11)°. In the crystal, the molecules are linked by O-H⋯O, O-H⋯N and C-H⋯O interactions, generating sheets.

Related literature

For structural studies of 4,4′-bipyridyl N,N′-dioxide, see: Lou & Huang (2007 ▶); Reddy et al. (2006 ▶). For the disulfide bond in polypeptide chains, see: Gortner & Hoffman (1941 ▶). For a related structure, see: Moreno-Fuquen et al. (2003 ▶). For hydrogen bonding, see: Etter (1990 ▶); Nardelli (1995 ▶).

Experimental

Crystal data

C14H10O4S2·0.5C10H8N2O2

M = 400.45

Monoclinic,

a = 21.314 (2) Å

b = 10.5621 (8) Å

c = 16.005 (8) Å

β = 105.412 (8)°

V = 3473.5 (18) Å3

Z = 8

Mo Kα radiation

μ = 0.34 mm−1

T = 291 K

0.22 × 0.18 × 0.12 mm

Data collection

Rigaku AFC-7S diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.951, T max = 0.990

3066 measured reflections

2781 independent reflections

2658 reflections with I > 2σ(I)

R int = 0.046

3 standard reflections every 120 min intensity decay: 0.9%

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.192

S = 1.11

2781 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −0.47 e Å−3

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993 ▶); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810018775/hg2676sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018775/hg2676Isup2.hkl

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

C14H10O4S2·0.5C10H8N2O2	F(000) = 1656
Mr = 400.45	Dx = 1.532 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -c 2yc	Cell parameters from 25 reflections
a = 21.314 (2) Å	θ = 10.3–19.1°
b = 10.5621 (8) Å	µ = 0.34 mm−1
c = 16.005 (8) Å	T = 291 K
β = 105.412 (8)°	Prism, pale-yellow
V = 3473.5 (18) Å3	0.22 × 0.18 × 0.12 mm
Z = 8

Rigaku AFC-7S diffractometer	2658 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	Rint = 0.046
graphite	θmax = 25.1°, θmin = 2.0°
ω/2θ scans	h = −25→24
Absorption correction: ψ scan (North et al., 1968)	k = 0→12
Tmin = 0.951, Tmax = 0.990	l = 0→19
3066 measured reflections	3 standard reflections every 120 min
2781 independent reflections	intensity decay: 0.9%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.065	H-atom parameters constrained
wR(F2) = 0.192	w = 1/[σ2(Fo2) + (0.1415P)2 + 4.1121P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
2781 reflections	Δρmax = 0.74 e Å−3
244 parameters	Δρmin = −0.47 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: none

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

	x	y	z	Uiso*/Ueq
S2	0.34651 (3)	0.02160 (7)	0.27473 (5)	0.0381 (3)
S1	0.25516 (3)	−0.05076 (8)	0.22805 (5)	0.0389 (3)
O2	0.13221 (10)	−0.1328 (3)	0.17027 (17)	0.0487 (6)
O4	0.55073 (13)	0.0281 (3)	0.4215 (2)	0.0761 (9)
O3	0.07037 (11)	−0.1051 (3)	0.03538 (17)	0.0589 (7)
H3	0.0408	−0.1159	0.0585	0.088*
O5	0.46308 (12)	0.1178 (2)	0.3372 (2)	0.0690 (9)
H55	0.4829	0.1832	0.3551	0.103*
C13	0.39868 (14)	−0.1151 (3)	0.2968 (2)	0.0359 (7)
C17	0.41418 (17)	−0.3405 (3)	0.2889 (2)	0.0472 (8)
H17	0.3975	−0.4197	0.2693	0.057*
C9	0.29901 (14)	−0.0579 (3)	0.0790 (2)	0.0374 (7)
H9	0.3401	−0.0404	0.1150	0.045*
C7	0.18433 (13)	−0.0960 (2)	0.0587 (2)	0.0337 (7)
C14	0.46425 (14)	−0.1032 (3)	0.3434 (2)	0.0379 (7)
C11	0.23059 (17)	−0.0955 (3)	−0.0634 (2)	0.0443 (8)
H11	0.2254	−0.1039	−0.1227	0.053*
C8	0.24617 (13)	−0.0705 (3)	0.1146 (2)	0.0335 (7)
C10	0.29099 (16)	−0.0710 (3)	−0.0088 (2)	0.0428 (8)
H10	0.3268	−0.0632	−0.0314	0.051*
C18	0.37493 (15)	−0.2348 (3)	0.2689 (2)	0.0421 (7)
H18	0.3320	−0.2438	0.2363	0.051*
C19	0.49747 (14)	0.0205 (3)	0.3733 (2)	0.0441 (8)
C6	0.12735 (14)	−0.1140 (3)	0.0947 (2)	0.0395 (8)
C15	0.50222 (15)	−0.2117 (3)	0.3643 (2)	0.0455 (8)
H15	0.5452	−0.2041	0.3969	0.055*
C16	0.47782 (16)	−0.3297 (3)	0.3378 (2)	0.0480 (8)
H16	0.5038	−0.4012	0.3527	0.058*
C12	0.17762 (15)	−0.1077 (3)	−0.0295 (2)	0.0422 (8)
H12	0.1368	−0.1239	−0.0665	0.051*
N1	0.08340 (11)	0.1895 (2)	0.91617 (17)	0.0361 (6)
O1	0.01985 (9)	0.1677 (2)	0.88364 (16)	0.0460 (6)
C4	0.18672 (14)	0.2206 (3)	0.8937 (2)	0.0399 (7)
H4	0.2127	0.2256	0.8555	0.048*
C1	0.10782 (14)	0.2062 (3)	1.0006 (2)	0.0449 (8)
H1	0.0804	0.2023	1.0371	0.054*
C3	0.21476 (12)	0.2373 (2)	0.98169 (19)	0.0311 (6)
C2	0.17312 (14)	0.2295 (3)	1.0351 (2)	0.0436 (8)
H2	0.1895	0.2400	1.0946	0.052*
C5	0.12157 (14)	0.1970 (3)	0.8619 (2)	0.0428 (7)
H5	0.1038	0.1863	0.8027	0.051*

	U11	U22	U33	U12	U13	U23
S2	0.0244 (4)	0.0417 (5)	0.0448 (6)	−0.0003 (3)	0.0033 (3)	−0.0071 (3)
S1	0.0220 (4)	0.0573 (5)	0.0375 (6)	−0.0022 (3)	0.0081 (3)	−0.0064 (3)
O2	0.0295 (11)	0.0734 (15)	0.0435 (17)	−0.0045 (10)	0.0101 (10)	0.0060 (11)
O4	0.0343 (15)	0.0647 (17)	0.109 (3)	−0.0041 (11)	−0.0167 (15)	−0.0058 (16)
O3	0.0253 (12)	0.092 (2)	0.0547 (16)	−0.0101 (11)	0.0029 (10)	0.0050 (13)
O5	0.0371 (13)	0.0452 (13)	0.105 (2)	−0.0065 (10)	−0.0149 (13)	−0.0014 (13)
C13	0.0301 (14)	0.0420 (15)	0.0366 (18)	0.0015 (11)	0.0104 (12)	0.0001 (12)
C17	0.056 (2)	0.0402 (16)	0.050 (2)	−0.0028 (14)	0.0208 (16)	−0.0012 (13)
C9	0.0296 (15)	0.0405 (15)	0.044 (2)	−0.0018 (11)	0.0129 (13)	−0.0009 (12)
C7	0.0281 (14)	0.0313 (13)	0.040 (2)	−0.0027 (10)	0.0060 (12)	0.0008 (11)
C14	0.0269 (14)	0.0446 (16)	0.044 (2)	0.0017 (11)	0.0127 (12)	0.0010 (13)
C11	0.054 (2)	0.0433 (16)	0.038 (2)	−0.0037 (14)	0.0158 (15)	−0.0013 (13)
C8	0.0247 (13)	0.0328 (13)	0.044 (2)	0.0005 (10)	0.0103 (12)	−0.0008 (11)
C10	0.0435 (17)	0.0418 (16)	0.050 (2)	−0.0021 (13)	0.0243 (15)	0.0017 (13)
C18	0.0367 (15)	0.0448 (16)	0.045 (2)	−0.0064 (12)	0.0107 (13)	−0.0047 (13)
C19	0.0232 (16)	0.0506 (18)	0.057 (2)	−0.0011 (12)	0.0079 (14)	−0.0019 (14)
C6	0.0256 (14)	0.0360 (15)	0.054 (2)	−0.0054 (11)	0.0055 (13)	−0.0040 (13)
C15	0.0336 (15)	0.0553 (19)	0.050 (2)	0.0077 (13)	0.0142 (13)	0.0056 (15)
C16	0.0466 (18)	0.0494 (18)	0.053 (2)	0.0115 (14)	0.0214 (15)	0.0080 (14)
C12	0.0401 (17)	0.0398 (16)	0.043 (2)	−0.0081 (12)	0.0049 (14)	−0.0055 (12)
N1	0.0223 (11)	0.0340 (12)	0.0523 (19)	0.0035 (9)	0.0108 (11)	0.0060 (10)
O1	0.0191 (10)	0.0503 (13)	0.0661 (16)	0.0003 (8)	0.0071 (9)	0.0062 (10)
C4	0.0290 (15)	0.0531 (17)	0.042 (2)	0.0012 (12)	0.0171 (13)	0.0015 (13)
C1	0.0281 (14)	0.065 (2)	0.047 (2)	−0.0006 (13)	0.0187 (14)	0.0026 (15)
C3	0.0253 (14)	0.0300 (12)	0.0416 (19)	0.0032 (10)	0.0152 (12)	0.0025 (11)
C2	0.0277 (14)	0.065 (2)	0.042 (2)	−0.0003 (13)	0.0157 (13)	−0.0003 (14)
C5	0.0316 (15)	0.0500 (17)	0.047 (2)	0.0025 (13)	0.0108 (14)	0.0025 (14)

S2—C13	1.799 (3)	C11—C10	1.375 (5)
S2—S1	2.0397 (10)	C11—C12	1.383 (5)
S1—C8	1.786 (3)	C11—H11	0.9300
O2—C6	1.203 (4)	C10—H10	0.9300
O4—C19	1.194 (4)	C18—H18	0.9300
O3—C6	1.331 (4)	C15—C16	1.373 (5)
O3—H3	0.8200	C15—H15	0.9300
O5—C19	1.305 (4)	C16—H16	0.9300
O5—H55	0.8200	C12—H12	0.9300
C13—C18	1.391 (4)	N1—C1	1.324 (4)
C13—C14	1.404 (4)	N1—O1	1.336 (3)
C17—C16	1.379 (5)	N1—C5	1.340 (4)
C17—C18	1.380 (5)	C4—C5	1.369 (4)
C17—H17	0.9300	C4—C3	1.387 (5)
C9—C10	1.376 (5)	C4—H4	0.9300
C9—C8	1.397 (4)	C1—C2	1.376 (4)
C9—H9	0.9300	C1—H1	0.9300
C7—C12	1.386 (5)	C3—C2	1.389 (4)
C7—C8	1.408 (4)	C3—C3i	1.484 (5)
C7—C6	1.488 (4)	C2—H2	0.9300
C14—C15	1.391 (4)	C5—H5	0.9300
C14—C19	1.502 (4)
C13—S2—S1	104.55 (10)	O4—C19—C14	123.5 (3)
C8—S1—S2	104.49 (9)	O5—C19—C14	112.5 (3)
C6—O3—H3	109.5	O2—C6—O3	123.2 (3)
C19—O5—H55	109.5	O2—C6—C7	123.3 (3)
C18—C13—C14	118.6 (3)	O3—C6—C7	113.5 (3)
C18—C13—S2	120.9 (2)	C16—C15—C14	121.7 (3)
C14—C13—S2	120.6 (2)	C16—C15—H15	119.2
C16—C17—C18	120.6 (3)	C14—C15—H15	119.2
C16—C17—H17	119.7	C15—C16—C17	119.0 (3)
C18—C17—H17	119.7	C15—C16—H16	120.5
C10—C9—C8	120.8 (3)	C17—C16—H16	120.5
C10—C9—H9	119.6	C11—C12—C7	121.2 (3)
C8—C9—H9	119.6	C11—C12—H12	119.4
C12—C7—C8	119.3 (3)	C7—C12—H12	119.4
C12—C7—C6	120.6 (3)	C1—N1—O1	120.2 (2)
C8—C7—C6	120.1 (3)	C1—N1—C5	120.7 (3)
C15—C14—C13	119.2 (3)	O1—N1—C5	119.0 (3)
C15—C14—C19	116.4 (3)	C5—C4—C3	121.4 (3)
C13—C14—C19	124.4 (3)	C5—C4—H4	119.3
C10—C11—C12	119.5 (3)	C3—C4—H4	119.3
C10—C11—H11	120.3	N1—C1—C2	121.0 (3)
C12—C11—H11	120.3	N1—C1—H1	119.5
C9—C8—C7	118.6 (3)	C2—C1—H1	119.5
C9—C8—S1	121.5 (2)	C4—C3—C2	116.3 (3)
C7—C8—S1	119.8 (2)	C4—C3—C3i	122.8 (3)
C11—C10—C9	120.6 (3)	C2—C3—C3i	120.9 (3)
C11—C10—H10	119.7	C1—C2—C3	120.5 (3)
C9—C10—H10	119.7	C1—C2—H2	119.8
C17—C18—C13	120.9 (3)	C3—C2—H2	119.8
C17—C18—H18	119.5	N1—C5—C4	120.0 (3)
C13—C18—H18	119.5	N1—C5—H5	120.0
O4—C19—O5	123.9 (3)	C4—C5—H5	120.0
C13—S2—S1—C8	−86.15 (14)	C13—C14—C19—O5	−12.7 (5)
S1—S2—C13—C18	10.1 (3)	C12—C7—C6—O2	163.0 (3)
S1—S2—C13—C14	−169.3 (2)	C8—C7—C6—O2	−15.1 (4)
C18—C13—C14—C15	−3.6 (5)	C12—C7—C6—O3	−18.1 (4)
S2—C13—C14—C15	175.9 (2)	C8—C7—C6—O3	163.8 (3)
C18—C13—C14—C19	176.5 (3)	C13—C14—C15—C16	2.3 (5)
S2—C13—C14—C19	−4.1 (4)	C19—C14—C15—C16	−177.7 (3)
C10—C9—C8—C7	−0.5 (4)	C14—C15—C16—C17	0.4 (5)
C10—C9—C8—S1	−178.8 (2)	C18—C17—C16—C15	−1.9 (5)
C12—C7—C8—C9	−0.1 (4)	C10—C11—C12—C7	−0.2 (5)
C6—C7—C8—C9	178.1 (3)	C8—C7—C12—C11	0.4 (4)
C12—C7—C8—S1	178.2 (2)	C6—C7—C12—C11	−177.7 (3)
C6—C7—C8—S1	−3.6 (4)	O1—N1—C1—C2	−179.6 (3)
S2—S1—C8—C9	10.4 (2)	C5—N1—C1—C2	−1.3 (5)
S2—S1—C8—C7	−167.9 (2)	C5—C4—C3—C2	−0.4 (4)
C12—C11—C10—C9	−0.3 (5)	C5—C4—C3—C3i	179.8 (3)
C8—C9—C10—C11	0.7 (5)	N1—C1—C2—C3	0.8 (5)
C16—C17—C18—C13	0.5 (5)	C4—C3—C2—C1	0.1 (5)
C14—C13—C18—C17	2.2 (5)	C3i—C3—C2—C1	179.8 (3)
S2—C13—C18—C17	−177.2 (3)	C1—N1—C5—C4	0.9 (5)
C15—C14—C19—O4	−9.3 (5)	O1—N1—C5—C4	179.3 (3)
C13—C14—C19—O4	170.6 (4)	C3—C4—C5—N1	−0.1 (5)
C15—C14—C19—O5	167.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H55···O1ii	0.82	1.77	2.583 (3)	174
O3—H3···O1iii	0.82	1.86	2.672 (3)	170
O5—H55···N1ii	0.82	2.50	3.255 (3)	154
C17—H17···O2iv	0.93	2.59	3.359 (4)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H55⋯O1i	0.82	1.77	2.583 (3)	174
O3—H3⋯O1ii	0.82	1.86	2.672 (3)	170
O5—H55⋯N1i	0.82	2.50	3.255 (3)	154
C17—H17⋯O2iii	0.93	2.59	3.359 (4)	140

Symmetry codes: (i) ; (ii) ; (iii) .