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In the title complex, C14H10O4S2·C10H8N2, hydrogen bonds between the carboxyl O atoms and the N atoms of 4,4'-bi­pyridine link the two different mol­ecules. There is a weak interaction between the carboxyl O atom and an H atom of 4,4'-bi­pyridine, contributing to the formation of a three-dimensional supramol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802012217/ob6147sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802012217/ob6147Isup2.hkl
Contains datablock I

CCDC reference: 193740

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.046
  • wR factor = 0.121
  • Data-to-parameter ratio = 12.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.693 0.962 Tmin' and Tmax expected: 0.888 0.962 RR' = 0.780 Please check that your absorption correction is appropriate.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SHELXTL (Siemens, 1994); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

2,2'-dithiodibenzoic acid–4,4'-bipyridine (1/1) top
Crystal data top
C14H10O4S2·C10H8N2F(000) = 960
Mr = 462.52Dx = 1.409 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.2079 (4) ÅCell parameters from 120 reflections
b = 13.2553 (5) Åθ = 1.9–25.0°
c = 17.8928 (8) ŵ = 0.28 mm1
β = 93.385 (1)°T = 293 K
V = 2180.07 (16) Å3Prism, colorless
Z = 40.42 × 0.20 × 0.14 mm
Data collection top
Siemens SMART CCD
diffractometer
3830 independent reflections
Radiation source: fine-focus sealed tube2973 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
h = 106
Tmin = 0.693, Tmax = 0.962k = 159
7140 measured reflectionsl = 2121
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0429P)2 + 1.4907P]
where P = (Fo2 + 2Fc2)/3
3830 reflections(Δ/σ)max = 0.010
297 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.25 e Å3
Special details top

Experimental. empirical from equivalent reflections (XEMP in SHELXTL; Siemens,1994)

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
S10.68684 (8)0.30855 (6)0.87306 (4)0.0553 (2)
S20.87711 (8)0.35287 (5)0.82797 (4)0.0552 (2)
C10.4461 (3)0.2934 (2)0.98629 (17)0.0532 (7)
C20.5699 (3)0.36058 (19)1.00705 (14)0.0446 (6)
C30.5707 (3)0.4136 (2)1.07440 (15)0.0560 (7)
H3A0.49400.40441.10530.067*
C40.6804 (3)0.4787 (3)1.09666 (17)0.0647 (8)
H4A0.67850.51311.14190.078*
C50.7929 (3)0.4923 (3)1.05094 (19)0.0714 (9)
H5A0.86780.53671.06510.086*
C60.7963 (3)0.4406 (2)0.98397 (17)0.0635 (8)
H6A0.87370.45080.95370.076*
C70.6864 (3)0.3738 (2)0.96089 (14)0.0464 (6)
C80.8357 (3)0.47331 (19)0.78607 (14)0.0437 (6)
C90.7005 (3)0.5184 (2)0.79205 (15)0.0520 (7)
H9A0.63020.48540.81820.062*
C100.6687 (3)0.6108 (2)0.76014 (16)0.0575 (7)
H10A0.57660.63850.76390.069*
C110.7718 (3)0.6628 (2)0.72256 (16)0.0572 (7)
H11A0.75080.72570.70170.069*
C120.9066 (3)0.6193 (2)0.71665 (15)0.0520 (7)
H12A0.97710.65420.69190.062*
C130.9403 (3)0.5248 (2)0.74655 (14)0.0444 (6)
C141.0848 (3)0.4795 (2)0.73485 (15)0.0510 (7)
C151.0385 (4)0.2614 (3)0.59545 (19)0.0801 (11)
H15A1.09660.21770.62480.096*
C161.0003 (4)0.3532 (3)0.48949 (19)0.0755 (10)
H16A1.03080.37490.44350.091*
C170.9077 (3)0.2907 (3)0.62130 (17)0.0687 (9)
H17A0.87920.26710.66710.082*
C180.8676 (3)0.3860 (3)0.51145 (17)0.0667 (9)
H18A0.81100.42900.48070.080*
C190.8186 (3)0.3552 (2)0.57926 (15)0.0509 (7)
C200.6771 (3)0.3907 (2)0.60615 (15)0.0480 (6)
C210.6210 (3)0.4844 (2)0.58595 (16)0.0566 (7)
H21A0.67160.52660.55520.068*
C220.5967 (3)0.3324 (2)0.65303 (18)0.0615 (8)
H22A0.63050.26950.66900.074*
C230.4663 (3)0.3686 (3)0.6757 (2)0.0704 (9)
H23A0.41360.32830.70690.084*
C240.4896 (3)0.5148 (2)0.61163 (17)0.0615 (8)
H24A0.45370.57810.59770.074*
O10.4377 (2)0.24212 (18)0.93084 (14)0.0802 (7)
O20.3449 (3)0.2955 (2)1.03516 (14)0.0808 (7)
O31.1631 (3)0.5337 (2)0.69107 (16)0.0918 (9)
O41.1255 (2)0.40065 (16)0.76232 (12)0.0621 (5)
N11.0866 (3)0.2922 (2)0.53039 (15)0.0723 (8)
N20.4121 (2)0.4575 (2)0.65544 (15)0.0639 (7)
HO21.246 (5)0.503 (4)0.683 (3)0.137 (18)*
HO10.270 (5)0.262 (4)1.019 (3)0.14 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0607 (4)0.0530 (4)0.0545 (4)0.0084 (3)0.0221 (3)0.0044 (3)
S20.0558 (4)0.0517 (4)0.0610 (4)0.0084 (3)0.0276 (3)0.0048 (3)
C10.0467 (16)0.0534 (17)0.0606 (17)0.0038 (13)0.0141 (13)0.0065 (14)
C20.0407 (14)0.0460 (15)0.0479 (14)0.0015 (11)0.0100 (11)0.0048 (12)
C30.0515 (17)0.0674 (19)0.0507 (16)0.0018 (14)0.0158 (13)0.0001 (14)
C40.0605 (19)0.081 (2)0.0522 (17)0.0007 (17)0.0029 (14)0.0134 (16)
C50.0504 (18)0.092 (2)0.072 (2)0.0149 (17)0.0031 (15)0.0195 (18)
C60.0427 (16)0.084 (2)0.0654 (19)0.0117 (15)0.0165 (14)0.0072 (17)
C70.0414 (14)0.0501 (15)0.0488 (15)0.0010 (12)0.0117 (11)0.0020 (12)
C80.0448 (14)0.0451 (14)0.0424 (14)0.0007 (12)0.0128 (11)0.0064 (11)
C90.0480 (15)0.0540 (17)0.0563 (16)0.0030 (13)0.0215 (13)0.0036 (13)
C100.0508 (16)0.0583 (18)0.0647 (18)0.0110 (14)0.0154 (14)0.0058 (15)
C110.0668 (19)0.0470 (16)0.0586 (17)0.0067 (14)0.0110 (14)0.0006 (13)
C120.0534 (16)0.0510 (16)0.0532 (16)0.0068 (13)0.0158 (13)0.0020 (13)
C130.0410 (14)0.0478 (15)0.0454 (14)0.0036 (12)0.0104 (11)0.0063 (12)
C140.0413 (15)0.0604 (18)0.0522 (16)0.0029 (13)0.0114 (12)0.0044 (14)
C150.060 (2)0.116 (3)0.065 (2)0.034 (2)0.0109 (16)0.001 (2)
C160.0590 (19)0.111 (3)0.0583 (19)0.012 (2)0.0213 (16)0.0009 (19)
C170.0585 (18)0.096 (3)0.0524 (17)0.0190 (18)0.0151 (14)0.0003 (17)
C180.0503 (17)0.096 (2)0.0550 (17)0.0129 (17)0.0107 (14)0.0028 (17)
C190.0405 (14)0.0674 (18)0.0452 (15)0.0007 (13)0.0046 (12)0.0115 (13)
C200.0371 (14)0.0569 (17)0.0504 (15)0.0045 (12)0.0042 (11)0.0095 (13)
C210.0434 (15)0.070 (2)0.0578 (17)0.0023 (14)0.0122 (13)0.0049 (15)
C220.0526 (17)0.0521 (17)0.082 (2)0.0024 (14)0.0184 (15)0.0040 (15)
C230.0538 (18)0.065 (2)0.096 (2)0.0116 (16)0.0307 (17)0.0014 (18)
C240.0433 (16)0.0679 (19)0.074 (2)0.0050 (14)0.0132 (14)0.0058 (16)
O10.0712 (15)0.0837 (16)0.0884 (17)0.0296 (12)0.0282 (12)0.0288 (14)
O20.0543 (13)0.109 (2)0.0821 (16)0.0252 (14)0.0304 (12)0.0098 (14)
O30.0594 (14)0.0919 (18)0.130 (2)0.0148 (13)0.0540 (15)0.0399 (16)
O40.0491 (11)0.0642 (13)0.0747 (14)0.0101 (10)0.0181 (10)0.0046 (11)
N10.0494 (15)0.104 (2)0.0652 (17)0.0165 (15)0.0146 (13)0.0125 (16)
N20.0405 (13)0.0683 (17)0.0849 (18)0.0030 (12)0.0201 (12)0.0030 (14)
Geometric parameters (Å, º) top
S1—C71.794 (3)C13—C141.486 (4)
S1—S22.0572 (10)C14—O41.205 (3)
S2—C81.795 (3)C14—O31.310 (3)
C1—O11.201 (3)C15—N11.334 (4)
C1—O21.315 (3)C15—C171.372 (4)
C1—C21.476 (4)C15—H15A0.9300
C2—C31.395 (4)C16—N11.323 (4)
C2—C71.403 (3)C16—C181.376 (4)
C3—C41.370 (4)C16—H16A0.9300
C3—H3A0.9300C17—C191.377 (4)
C4—C51.369 (4)C17—H17A0.9300
C4—H4A0.9300C18—C191.381 (4)
C5—C61.382 (4)C18—H18A0.9300
C5—H5A0.9300C19—C201.491 (4)
C6—C71.389 (4)C20—C211.384 (4)
C6—H6A0.9300C20—C221.387 (4)
C8—C91.390 (4)C21—C241.380 (4)
C8—C131.405 (3)C21—H21A0.9300
C9—C101.376 (4)C22—C231.375 (4)
C9—H9A0.9300C22—H22A0.9300
C10—C111.380 (4)C23—N21.322 (4)
C10—H10A0.9300C23—H23A0.9300
C11—C121.378 (4)C24—N21.329 (4)
C11—H11A0.9300C24—H24A0.9300
C12—C131.390 (4)O2—HO10.86 (5)
C12—H12A0.9300O3—HO20.88 (5)
C7—S1—S2104.59 (9)C12—C13—C14119.4 (2)
C8—S2—S1104.65 (9)C8—C13—C14121.4 (2)
O1—C1—O2123.2 (3)O4—C14—O3123.4 (3)
O1—C1—C2124.1 (2)O4—C14—C13123.5 (2)
O2—C1—C2112.7 (3)O3—C14—C13113.0 (3)
C3—C2—C7118.7 (2)N1—C15—C17123.4 (3)
C3—C2—C1119.1 (2)N1—C15—H15A118.3
C7—C2—C1122.2 (2)C17—C15—H15A118.3
C4—C3—C2122.3 (3)N1—C16—C18123.4 (3)
C4—C3—H3A118.8N1—C16—H16A118.3
C2—C3—H3A118.8C18—C16—H16A118.3
C5—C4—C3118.7 (3)C15—C17—C19119.9 (3)
C5—C4—H4A120.7C15—C17—H17A120.0
C3—C4—H4A120.7C19—C17—H17A120.0
C4—C5—C6120.6 (3)C16—C18—C19119.9 (3)
C4—C5—H5A119.7C16—C18—H18A120.0
C6—C5—H5A119.7C19—C18—H18A120.0
C5—C6—C7121.4 (3)C17—C19—C18116.6 (3)
C5—C6—H6A119.3C17—C19—C20121.6 (2)
C7—C6—H6A119.3C18—C19—C20121.8 (3)
C6—C7—C2118.3 (2)C21—C20—C22116.9 (2)
C6—C7—S1121.9 (2)C21—C20—C19121.3 (2)
C2—C7—S1119.8 (2)C22—C20—C19121.8 (3)
C9—C8—C13118.3 (2)C24—C21—C20119.8 (3)
C9—C8—S2121.3 (2)C24—C21—H21A120.1
C13—C8—S2120.46 (19)C20—C21—H21A120.1
C10—C9—C8121.4 (3)C23—C22—C20119.4 (3)
C10—C9—H9A119.3C23—C22—H22A120.3
C8—C9—H9A119.3C20—C22—H22A120.3
C9—C10—C11120.7 (3)N2—C23—C22123.5 (3)
C9—C10—H10A119.6N2—C23—H23A118.3
C11—C10—H10A119.6C22—C23—H23A118.3
C12—C11—C10118.5 (3)N2—C24—C21122.7 (3)
C12—C11—H11A120.7N2—C24—H24A118.6
C10—C11—H11A120.7C21—C24—H24A118.6
C11—C12—C13121.9 (2)C1—O2—HO1110 (3)
C11—C12—H12A119.0C14—O3—HO2111 (3)
C13—C12—H12A119.0C16—N1—C15116.7 (3)
C12—C13—C8119.2 (2)C23—N2—C24117.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—HO1···N1i0.86 (5)1.86 (3)2.644 (2)151 (3)
C24—H24A···O1ii0.932.463.188 (3)135
O3—HO2···N2iii0.88 (5)1.75 (3)2.618 (5)170 (5)
C4—H4A···O4iv0.932.673.404 (1)136
Symmetry codes: (i) x1, y+1/2, z+1/2; (ii) x+1, y+1/2, z+3/2; (iii) x+1, y, z; (iv) x+2, y+1, z+2.
 

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