2,2′-(Disulfanediyl)dibenzoic acid–N,N′-bis­(3-pyridyl­meth­yl)ethane­diamide (1/1)

Arman, H.D.; Miller, T.; Poplaukhin, P.; Tiekink, E.R.T.

doi:10.1107/S1600536810036494

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages o2590-o2591

doi:10.1107/S1600536810036494

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2,2′-(Disulfanediyl)dibenzoic acid–N,N′-bis(3-pyridylmethyl)ethanediamide (1/1)

Hadi D. Arman,^a Tyler Miller,^a Pavel Poplaukhin ^b and Edward R. T. Tiekink ^c ^*

^aDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA, ^bChemical Abstracts Service, 2540 Olentangy River Rd, Columbus, Ohio 43202, USA, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 12 September 2010; accepted 13 September 2010; online 18 September 2010)

The asymmetric unit of the title cocrystal, C₁₄H₁₄N₄O₂·C₁₄H₁₀O₄S₂, comprises a twisted 2,2′-(disulfanediyl)dibenzoic acid molecule [dihedral angle between the benzene rings = 76.35 (10)°] and a U-shaped N,N′-bis(3-pyridylmethyl)ethanediamide molecule with the pyridyl groups lying to the same side of the central diamide moiety [C—C—C—N = 113.8 (2) and −117.6 (2)°]. The latter aggregate into supramolecular tapes propagating along the a axis via centrosymmetric eight-membered amide {⋯OCNH}₂ synthons. Intramolecular N—H⋯O hydrogen bonds are observed. The 2,2′-(disulfanediyl)dibenzoic acid molecules form carboxyl–pyridine O—H⋯N hydrogen bonds, bridging a pyridine residue below the plane of the tape and one above the plane with two intervening N,N′-bis(3-pyridylmethyl)ethanediamide molecules. The supramolecular chains are consolidated in the crystal packing by C—H⋯O contacts. An intermolecular C—H⋯S interaction also occurs.

Related literature

For related studies on co-crystal formation involving 2-[(2-carboxyphenyl)disulfanyl]benzoic acid, see: Broker & Tiekink (2007 , 2010 ); Broker et al. (2008 ); Arman et al. (2010 ). For crystal engineering studies on N,N′-bis(3-pyridylmethyl)ethanediamide, see: Poplaukhin & Tiekink (2010 ).

Experimental

Crystal data

C₁₄H₁₄N₄O₂·C₁₄H₁₀O₄S₂
M_r = 576.63
Triclinic, $[P \overline 1]$
a = 10.015 (3) Å
b = 10.310 (3) Å
c = 14.795 (4) Å
α = 86.910 (16)°
β = 78.052 (15)°
γ = 69.554 (10)°
V = 1400.1 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 98 K
0.50 × 0.19 × 0.10 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.755, T_max = 1.000
10806 measured reflections
6365 independent reflections
5644 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.120
S = 1.09
6365 reflections
373 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1n⋯O2	0.88 (1)	2.37 (2)	2.736 (2)	105 (1)
N2—H1n⋯O2ⁱ	0.88 (1)	2.03 (1)	2.789 (3)	144 (2)
N3—H2n⋯O1	0.88 (1)	2.37 (2)	2.698 (2)	103 (1)
N3—H2n⋯O1ⁱⁱ	0.88 (1)	1.97 (1)	2.773 (3)	151 (2)
O4—H1o⋯N1ⁱⁱⁱ	0.84 (2)	1.83 (2)	2.664 (3)	175 (1)
O6—H2o⋯N4ⁱⁱ	0.84 (2)	1.80 (2)	2.641 (3)	179 (4)
C2—H2⋯O3^iv	0.95	2.53	3.220 (3)	129
C3—H3⋯O1^v	0.95	2.48	3.261 (3)	139
C9—H9b⋯S1ⁱ	0.99	2.73	3.370 (2)	123
Symmetry codes: (i) -x+2, -y, -z; (ii) -x+1, -y, -z; (iii) x+1, y, z; (iv) x-1, y, z; (v) -x+1, -y+1, -z.

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036494/hg2712sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810036494/hg2712Isup2.hkl

checkCIF report

Comment top

As a continuation of studies into the phenomenon of co-crystallization of 2-[(2-carboxyphenyl)disulfanyl]benzoic acid (Broker & Tiekink, 2007; Broker et al., 2008; Broker & Tiekink, 2010; Arman et al., 2010), the co-crystallization of 2,2'-(disulfanediyl)dibenzoic acid and N,N'-bis(3-pyridylmethyl)ethanediamide (Poplaukhin & Tiekink, 2010) was investigated. The asymmetric unit of the resulting co-crystal contains one molecule of 2,2'-(disulfanediyl)dibenzoic acid, Fig. 1, and N,N'-bis(3-pyridylmethyl)ethanediamide, Fig. 2.

The 2,2'-(disulfanediyl)dibenzoic acid molecule adopts the expected conformation (Broker & Tiekink, 2007), stabilized in part by two close S···O(carbonyl) interactions, i.e. S1···O3 = 2.6520 (18) Å and S2···O5 = 2.6593 (19) Å; the dihedral angle formed between the benzene rings = 76.35 (10) °. The N,N'-bis(3-pyridylmethyl)ethanediamide molecule adopts a U-shape with the pyridyl groups lying to the same side of the central diamide moiety [C2—C1—C6—N2 = 113.8 (2) ° and N3—C9—C10—C11 = -117.6 (2) °]; the dihedral angle formed between the pyridyl rings = 72.24 (12) °. The pyridine-N atoms are each directed to the same side of the molecule.

Supramolecular tapes are formed comprising alternately orientated U-shaped N,N'-bis(3-pyridylmethyl)ethanediamide molecules and mediated by centrosymmetric eight-membered amide {···OCNH}₂ synthons, Fig. 3; intramolecular N—H···O contacts are also noted, Table 1. This arrangement results in successive pairs of pyridine residues of the N,N'-bis(3-pyridylmethyl)oxamide molecules being orientated above and below the plane of the tape. The 2,2'-(disulfanediyl)dibenzoic acid molecules form carboxylic acid-OH···N-pyridine interactions so that a bridge is formed between a pyridine residue below the plane of the tape and one above the plane with two intervening N,N'-bis(3-pyridylmethyl)oxamide molecules. In summary, amide-mediated chains are gird by N,N'-bis(3-pyridylmethyl)oxamide molecules as highlighted in the end-on view shown in Fig. 4. The tapes are orientated along the a direction with the most prominent connection between them being of the type C—H···O, Fig. 5.

Related literature top

For related studies on co-crystal formation involving 2-[(2-carboxyphenyl)disulfanyl]benzoic acid, see: Broker & Tiekink (2007, 2010); Broker et al. (2008); Arman et al. (2010). For crystal engineering studies on N,N'-bis(3-pyridylmethyl)ethanediamide, see: Poplaukhin & Tiekink (2010).

Experimental top

Equimolar amounts of 2-[(2-carboxyphenyl)disulfanyl]benzoic acid (Fluka) and N,N'-bis(3-pyridylmethyl)ethanediamide (Poplaukhin & Tiekink, 2010) were dissolved in a 1:1 ethanol/chloroform mixture. Crystals were harvested after a few days of slow evaporation.

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); cell refinement: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); data reduction: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of 2-[(2-carboxyphenyl)disulfanyl]benzoic acid found in the structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. Molecular structure of N,N'-bis(3-pyridylmethyl)ethanediamide found in the structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 3. Supramolecular chain along the a axis in (I). The O—H···N and N—H···O hydrogen bonds are shown as orange dashed lines.
	Fig. 4. End-on view of the supramolecular chain along the a axis in (I). The O—H···N and N—H···O hydrogen bonds are shown as orange dashed lines.
	Fig. 5. View in projection down the a axis in (I) showing the crystal packing. The O—H···N and N—H···O hydrogen bonds are shown as orange dashed lines, and C—H···O interactions are shown as blue dashed lines.

2,2'-(disulfanediyl)dibenzoic acid–N,N'-bis(3-pyridylmethyl)ethanediamide (1/1) top

Crystal data top

C₁₄H₁₄N₄O₂·C₁₄H₁₀O₄S₂	Z = 2
M_r = 576.63	F(000) = 600
Triclinic, P1	D_x = 1.368 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 10.015 (3) Å	Cell parameters from 5721 reflections
b = 10.310 (3) Å	θ = 2.2–40.6°
c = 14.795 (4) Å	µ = 0.24 mm⁻¹
α = 86.910 (16)°	T = 98 K
β = 78.052 (15)°	Block, colourless
γ = 69.554 (10)°	0.50 × 0.19 × 0.10 mm
V = 1400.1 (7) Å³

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	6365 independent reflections
Radiation source: fine-focus sealed tube	5644 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→13
T_min = 0.755, T_max = 1.000	k = −12→13
10806 measured reflections	l = −18→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0472P)² + 0.7689P] where P = (F_o² + 2F_c²)/3
6365 reflections	(Δ/σ)_max = 0.001
373 parameters	Δρ_max = 0.36 e Å⁻³
4 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₄H₁₄N₄O₂·C₁₄H₁₀O₄S₂	γ = 69.554 (10)°
M_r = 576.63	V = 1400.1 (7) Å³
Triclinic, P1	Z = 2
a = 10.015 (3) Å	Mo Kα radiation
b = 10.310 (3) Å	µ = 0.24 mm⁻¹
c = 14.795 (4) Å	T = 98 K
α = 86.910 (16)°	0.50 × 0.19 × 0.10 mm
β = 78.052 (15)°

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	6365 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	5644 reflections with I > 2σ(I)
T_min = 0.755, T_max = 1.000	R_int = 0.031
10806 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	4 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.36 e Å⁻³
6365 reflections	Δρ_min = −0.41 e Å⁻³
373 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

	x	y	z	U_iso*/U_eq
S1	0.95625 (5)	0.47011 (5)	0.27148 (3)	0.02334 (12)
S2	0.77520 (5)	0.41447 (5)	0.31055 (3)	0.02470 (12)
O1	0.57298 (14)	0.09350 (15)	0.05444 (10)	0.0277 (3)
O2	0.92729 (14)	−0.08648 (15)	−0.06739 (10)	0.0274 (3)
O3	1.18914 (15)	0.52923 (14)	0.18911 (10)	0.0261 (3)
O4	1.20535 (15)	0.73668 (15)	0.14860 (11)	0.0292 (3)
H1o	1.2938 (7)	0.688 (2)	0.1330 (18)	0.044*
O5	0.57421 (16)	0.29499 (15)	0.34728 (10)	0.0274 (3)
O6	0.49044 (17)	0.21673 (18)	0.48313 (10)	0.0324 (4)
H2o	0.437 (2)	0.194 (3)	0.4549 (17)	0.049*
N1	0.48914 (18)	0.59287 (18)	0.10362 (12)	0.0262 (4)
N2	0.78541 (17)	0.12250 (17)	0.06156 (11)	0.0222 (3)
H1n	0.8801 (4)	0.093 (2)	0.0407 (14)	0.027*
N3	0.70914 (17)	−0.09173 (17)	−0.08631 (12)	0.0231 (3)
H2n	0.6141 (4)	−0.064 (2)	−0.0674 (15)	0.028*
N4	0.67717 (19)	−0.14651 (19)	−0.39347 (12)	0.0283 (4)
C1	0.6801 (2)	0.3730 (2)	0.10738 (13)	0.0212 (4)
C2	0.5347 (2)	0.4577 (2)	0.12348 (13)	0.0233 (4)
H2	0.4635	0.4178	0.1500	0.028*
C3	0.5902 (2)	0.6486 (2)	0.06698 (16)	0.0332 (5)
H3	0.5598	0.7446	0.0540	0.040*
C4	0.7377 (2)	0.5712 (3)	0.04726 (17)	0.0363 (5)
H4	0.8066	0.6133	0.0200	0.044*
C5	0.7829 (2)	0.4320 (2)	0.06776 (15)	0.0293 (4)
H5	0.8834	0.3773	0.0548	0.035*
C6	0.7231 (2)	0.2239 (2)	0.13762 (13)	0.0222 (4)
H6A	0.7947	0.2082	0.1778	0.027*
H6B	0.6360	0.2085	0.1750	0.027*
C7	0.7054 (2)	0.06452 (19)	0.02830 (13)	0.0209 (4)
C8	0.7929 (2)	−0.0458 (2)	−0.04751 (13)	0.0225 (4)
C9	0.7676 (2)	−0.2038 (2)	−0.15588 (14)	0.0249 (4)
H9A	0.7105	−0.2664	−0.1422	0.030*
H9B	0.8694	−0.2581	−0.1517	0.030*
C10	0.7639 (2)	−0.1524 (2)	−0.25316 (14)	0.0253 (4)
C11	0.6821 (2)	−0.1873 (2)	−0.30620 (14)	0.0253 (4)
H11	0.6266	−0.2430	−0.2794	0.030*
C12	0.7536 (3)	−0.0680 (3)	−0.43111 (17)	0.0391 (5)
H12	0.7508	−0.0393	−0.4930	0.047*
C13	0.8371 (4)	−0.0266 (4)	−0.3833 (2)	0.0588 (8)
H13	0.8907	0.0300	−0.4115	0.071*
C14	0.8410 (3)	−0.0696 (3)	−0.29329 (19)	0.0517 (7)
H14	0.8972	−0.0418	−0.2590	0.062*
C15	0.9789 (2)	0.7291 (2)	0.23181 (13)	0.0219 (4)
C16	0.8894 (2)	0.65541 (19)	0.27535 (13)	0.0220 (4)
C17	0.7493 (2)	0.7285 (2)	0.32319 (14)	0.0269 (4)
H17	0.6887	0.6794	0.3536	0.032*
C18	0.6974 (2)	0.8720 (2)	0.32683 (16)	0.0321 (5)
H18	0.6020	0.9204	0.3601	0.039*
C19	0.7833 (2)	0.9455 (2)	0.28253 (16)	0.0327 (5)
H19	0.7472	1.0438	0.2850	0.039*
C20	0.9230 (2)	0.8740 (2)	0.23438 (14)	0.0273 (4)
H20	0.9814	0.9243	0.2027	0.033*
C21	1.1338 (2)	0.6551 (2)	0.18689 (13)	0.0221 (4)
C22	0.7479 (2)	0.40288 (19)	0.43378 (13)	0.0220 (4)
C23	0.6509 (2)	0.3389 (2)	0.48074 (13)	0.0223 (4)
C24	0.6283 (2)	0.3319 (2)	0.57712 (14)	0.0279 (4)
H24	0.5644	0.2871	0.6089	0.033*
C25	0.6978 (2)	0.3893 (2)	0.62702 (15)	0.0315 (5)
H25	0.6802	0.3855	0.6925	0.038*
C26	0.7928 (2)	0.4519 (2)	0.58043 (15)	0.0293 (4)
H26	0.8411	0.4909	0.6142	0.035*
C27	0.8185 (2)	0.4583 (2)	0.48487 (15)	0.0274 (4)
H27	0.8849	0.5009	0.4538	0.033*
C28	0.5689 (2)	0.2819 (2)	0.43016 (14)	0.0230 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0235 (2)	0.0226 (2)	0.0238 (3)	−0.00938 (18)	−0.00082 (18)	−0.00458 (17)
S2	0.0287 (3)	0.0311 (3)	0.0190 (2)	−0.0164 (2)	−0.00315 (19)	−0.00354 (18)
O1	0.0151 (6)	0.0334 (8)	0.0350 (8)	−0.0080 (6)	−0.0035 (6)	−0.0117 (6)
O2	0.0158 (6)	0.0346 (8)	0.0316 (8)	−0.0075 (6)	−0.0036 (6)	−0.0119 (6)
O3	0.0243 (7)	0.0246 (7)	0.0284 (8)	−0.0087 (6)	−0.0019 (6)	−0.0029 (6)
O4	0.0231 (7)	0.0279 (8)	0.0345 (8)	−0.0095 (6)	−0.0013 (6)	0.0058 (6)
O5	0.0319 (7)	0.0352 (8)	0.0198 (7)	−0.0171 (6)	−0.0054 (6)	−0.0021 (6)
O6	0.0339 (8)	0.0519 (10)	0.0230 (8)	−0.0280 (8)	−0.0084 (6)	0.0042 (7)
N1	0.0260 (8)	0.0275 (9)	0.0246 (9)	−0.0091 (7)	−0.0045 (7)	0.0016 (7)
N2	0.0174 (7)	0.0259 (8)	0.0224 (8)	−0.0060 (6)	−0.0026 (6)	−0.0078 (6)
N3	0.0165 (7)	0.0258 (8)	0.0271 (9)	−0.0065 (6)	−0.0036 (6)	−0.0092 (7)
N4	0.0274 (9)	0.0337 (9)	0.0264 (9)	−0.0136 (7)	−0.0053 (7)	−0.0017 (7)
C1	0.0234 (9)	0.0260 (9)	0.0156 (9)	−0.0097 (8)	−0.0041 (7)	−0.0029 (7)
C2	0.0229 (9)	0.0274 (10)	0.0206 (10)	−0.0106 (8)	−0.0030 (7)	−0.0009 (7)
C3	0.0323 (11)	0.0325 (11)	0.0360 (12)	−0.0133 (9)	−0.0082 (9)	0.0091 (9)
C4	0.0283 (11)	0.0410 (13)	0.0415 (13)	−0.0176 (10)	−0.0044 (9)	0.0127 (10)
C5	0.0221 (9)	0.0364 (11)	0.0295 (11)	−0.0105 (8)	−0.0059 (8)	0.0048 (9)
C6	0.0227 (9)	0.0259 (9)	0.0186 (9)	−0.0086 (7)	−0.0038 (7)	−0.0046 (7)
C7	0.0183 (8)	0.0229 (9)	0.0232 (10)	−0.0078 (7)	−0.0063 (7)	−0.0020 (7)
C8	0.0198 (9)	0.0254 (9)	0.0229 (10)	−0.0074 (7)	−0.0047 (7)	−0.0035 (7)
C9	0.0245 (9)	0.0247 (9)	0.0262 (10)	−0.0069 (8)	−0.0069 (8)	−0.0085 (8)
C10	0.0244 (9)	0.0281 (10)	0.0241 (10)	−0.0097 (8)	−0.0037 (8)	−0.0069 (8)
C11	0.0249 (9)	0.0293 (10)	0.0242 (10)	−0.0125 (8)	−0.0035 (8)	−0.0043 (8)
C12	0.0478 (14)	0.0460 (14)	0.0329 (13)	−0.0273 (12)	−0.0095 (10)	0.0035 (10)
C13	0.082 (2)	0.080 (2)	0.0464 (16)	−0.0664 (19)	−0.0207 (15)	0.0162 (15)
C14	0.0701 (19)	0.076 (2)	0.0388 (14)	−0.0562 (17)	−0.0209 (13)	0.0040 (13)
C15	0.0218 (9)	0.0252 (9)	0.0187 (9)	−0.0076 (7)	−0.0046 (7)	−0.0005 (7)
C16	0.0248 (9)	0.0230 (9)	0.0190 (9)	−0.0079 (7)	−0.0057 (7)	−0.0022 (7)
C17	0.0247 (10)	0.0277 (10)	0.0264 (11)	−0.0080 (8)	−0.0027 (8)	−0.0001 (8)
C18	0.0261 (10)	0.0280 (11)	0.0333 (12)	−0.0020 (8)	0.0004 (8)	−0.0006 (8)
C19	0.0372 (12)	0.0220 (10)	0.0323 (12)	−0.0042 (9)	−0.0034 (9)	0.0013 (8)
C20	0.0298 (10)	0.0251 (10)	0.0262 (10)	−0.0107 (8)	−0.0030 (8)	0.0037 (8)
C21	0.0232 (9)	0.0276 (10)	0.0175 (9)	−0.0108 (8)	−0.0044 (7)	−0.0003 (7)
C22	0.0228 (9)	0.0231 (9)	0.0197 (9)	−0.0073 (7)	−0.0036 (7)	−0.0038 (7)
C23	0.0207 (9)	0.0256 (9)	0.0212 (10)	−0.0073 (7)	−0.0062 (7)	−0.0015 (7)
C24	0.0250 (10)	0.0384 (11)	0.0219 (10)	−0.0129 (9)	−0.0046 (8)	0.0003 (8)
C25	0.0325 (11)	0.0457 (13)	0.0180 (10)	−0.0143 (10)	−0.0069 (8)	−0.0015 (9)
C26	0.0301 (10)	0.0372 (11)	0.0253 (11)	−0.0139 (9)	−0.0108 (8)	−0.0039 (8)
C27	0.0272 (10)	0.0312 (10)	0.0277 (11)	−0.0126 (8)	−0.0086 (8)	−0.0030 (8)
C28	0.0195 (9)	0.0252 (9)	0.0240 (10)	−0.0076 (7)	−0.0031 (7)	−0.0030 (7)

Geometric parameters (Å, º) top

S1—C16	1.790 (2)	C9—C10	1.510 (3)
S1—S2	2.0514 (9)	C9—H9A	0.9900
S2—C22	1.791 (2)	C9—H9B	0.9900
O1—C7	1.233 (2)	C10—C14	1.376 (3)
O2—C8	1.237 (2)	C10—C11	1.386 (3)
O3—C21	1.222 (2)	C11—H11	0.9500
O4—C21	1.321 (2)	C12—C13	1.382 (3)
O4—H1o	0.841 (15)	C12—H12	0.9500
O5—C28	1.219 (2)	C13—C14	1.384 (4)
O6—C28	1.319 (2)	C13—H13	0.9500
O6—H2o	0.84 (2)	C14—H14	0.9500
N1—C3	1.339 (3)	C15—C20	1.400 (3)
N1—C2	1.343 (3)	C15—C16	1.407 (3)
N2—C7	1.331 (2)	C15—C21	1.494 (3)
N2—C6	1.459 (2)	C16—C17	1.395 (3)
N2—H1n	0.880 (12)	C17—C18	1.387 (3)
N3—C8	1.328 (2)	C17—H17	0.9500
N3—C9	1.464 (2)	C18—C19	1.382 (3)
N3—H2n	0.880 (13)	C18—H18	0.9500
N4—C12	1.326 (3)	C19—C20	1.389 (3)
N4—C11	1.342 (3)	C19—H19	0.9500
C1—C5	1.386 (3)	C20—H20	0.9500
C1—C2	1.390 (3)	C22—C27	1.396 (3)
C1—C6	1.514 (3)	C22—C23	1.407 (3)
C2—H2	0.9500	C23—C24	1.399 (3)
C3—C4	1.388 (3)	C23—C28	1.489 (3)
C3—H3	0.9500	C24—C25	1.388 (3)
C4—C5	1.383 (3)	C24—H24	0.9500
C4—H4	0.9500	C25—C26	1.381 (3)
C5—H5	0.9500	C25—H25	0.9500
C6—H6A	0.9900	C26—C27	1.386 (3)
C6—H6B	0.9900	C26—H26	0.9500
C7—C8	1.534 (3)	C27—H27	0.9500

C16—S1—S2	105.30 (7)	N4—C12—C13	122.2 (2)
C22—S2—S1	105.35 (7)	N4—C12—H12	118.9
C21—O4—H1O	108 (2)	C13—C12—H12	118.9
C28—O6—H2O	113 (2)	C12—C13—C14	118.5 (2)
C3—N1—C2	117.81 (18)	C12—C13—H13	120.8
C7—N2—C6	121.95 (16)	C14—C13—H13	120.8
C7—N2—H1N	119 (2)	C10—C14—C13	120.4 (2)
C6—N2—H1N	119 (2)	C10—C14—H14	119.8
C8—N3—C9	123.05 (16)	C13—C14—H14	119.8
C8—N3—H2N	122 (2)	C20—C15—C16	119.16 (18)
C9—N3—H2N	114 (2)	C20—C15—C21	119.88 (17)
C12—N4—C11	118.65 (18)	C16—C15—C21	120.90 (17)
C5—C1—C2	117.70 (18)	C17—C16—C15	119.16 (18)
C5—C1—C6	121.89 (18)	C17—C16—S1	120.49 (15)
C2—C1—C6	120.31 (17)	C15—C16—S1	120.34 (15)
N1—C2—C1	123.64 (18)	C18—C17—C16	120.66 (19)
N1—C2—H2	118.2	C18—C17—H17	119.7
C1—C2—H2	118.2	C16—C17—H17	119.7
N1—C3—C4	122.4 (2)	C19—C18—C17	120.6 (2)
N1—C3—H3	118.8	C19—C18—H18	119.7
C4—C3—H3	118.8	C17—C18—H18	119.7
C5—C4—C3	119.1 (2)	C18—C19—C20	119.35 (19)
C5—C4—H4	120.4	C18—C19—H19	120.3
C3—C4—H4	120.4	C20—C19—H19	120.3
C4—C5—C1	119.31 (19)	C19—C20—C15	121.01 (19)
C4—C5—H5	120.3	C19—C20—H20	119.5
C1—C5—H5	120.3	C15—C20—H20	119.5
N2—C6—C1	114.21 (16)	O3—C21—O4	123.62 (18)
N2—C6—H6A	108.7	O3—C21—C15	121.66 (17)
C1—C6—H6A	108.7	O4—C21—C15	114.67 (17)
N2—C6—H6B	108.7	C27—C22—C23	118.96 (18)
C1—C6—H6B	108.7	C27—C22—S2	121.54 (16)
H6A—C6—H6B	107.6	C23—C22—S2	119.48 (14)
O1—C7—N2	124.84 (18)	C24—C23—C22	119.26 (17)
O1—C7—C8	121.27 (16)	C24—C23—C28	119.37 (18)
N2—C7—C8	113.89 (16)	C22—C23—C28	121.35 (17)
O2—C8—N3	125.32 (18)	C25—C24—C23	121.1 (2)
O2—C8—C7	121.87 (16)	C25—C24—H24	119.5
N3—C8—C7	112.80 (16)	C23—C24—H24	119.5
N3—C9—C10	113.04 (17)	C26—C25—C24	119.32 (19)
N3—C9—H9A	109.0	C26—C25—H25	120.3
C10—C9—H9A	109.0	C24—C25—H25	120.3
N3—C9—H9B	109.0	C25—C26—C27	120.63 (18)
C10—C9—H9B	109.0	C25—C26—H26	119.7
H9A—C9—H9B	107.8	C27—C26—H26	119.7
C14—C10—C11	117.0 (2)	C26—C27—C22	120.76 (19)
C14—C10—C9	122.02 (18)	C26—C27—H27	119.6
C11—C10—C9	121.01 (18)	C22—C27—H27	119.6
N4—C11—C10	123.35 (19)	O5—C28—O6	123.38 (17)
N4—C11—H11	118.3	O5—C28—C23	122.65 (18)
C10—C11—H11	118.3	O6—C28—C23	113.97 (17)

C16—S1—S2—C22	−88.85 (9)	C20—C15—C16—S1	178.78 (15)
C3—N1—C2—C1	−0.6 (3)	C21—C15—C16—S1	−4.0 (2)
C5—C1—C2—N1	−0.7 (3)	S2—S1—C16—C17	16.77 (17)
C6—C1—C2—N1	175.91 (17)	S2—S1—C16—C15	−164.61 (14)
C2—N1—C3—C4	1.6 (3)	C15—C16—C17—C18	1.0 (3)
N1—C3—C4—C5	−1.4 (4)	S1—C16—C17—C18	179.59 (17)
C3—C4—C5—C1	0.1 (3)	C16—C17—C18—C19	0.5 (3)
C2—C1—C5—C4	0.9 (3)	C17—C18—C19—C20	−0.3 (3)
C6—C1—C5—C4	−175.63 (19)	C18—C19—C20—C15	−1.4 (3)
C7—N2—C6—C1	−96.1 (2)	C16—C15—C20—C19	2.9 (3)
C5—C1—C6—N2	−69.8 (2)	C21—C15—C20—C19	−174.42 (19)
C2—C1—C6—N2	113.8 (2)	C20—C15—C21—O3	174.69 (18)
C6—N2—C7—O1	3.2 (3)	C16—C15—C21—O3	−2.5 (3)
C6—N2—C7—C8	−176.49 (17)	C20—C15—C21—O4	−2.8 (3)
C9—N3—C8—O2	3.2 (3)	C16—C15—C21—O4	179.98 (17)
C9—N3—C8—C7	−175.71 (17)	S1—S2—C22—C27	14.52 (18)
O1—C7—C8—O2	−172.03 (19)	S1—S2—C22—C23	−166.75 (14)
N2—C7—C8—O2	7.7 (3)	C27—C22—C23—C24	−0.3 (3)
O1—C7—C8—N3	6.9 (3)	S2—C22—C23—C24	−179.10 (15)
N2—C7—C8—N3	−173.41 (17)	C27—C22—C23—C28	178.05 (18)
C8—N3—C9—C10	−101.3 (2)	S2—C22—C23—C28	−0.7 (3)
N3—C9—C10—C14	62.5 (3)	C22—C23—C24—C25	1.3 (3)
N3—C9—C10—C11	−117.6 (2)	C28—C23—C24—C25	−177.13 (19)
C12—N4—C11—C10	−0.4 (3)	C23—C24—C25—C26	−1.3 (3)
C14—C10—C11—N4	1.1 (3)	C24—C25—C26—C27	0.3 (3)
C9—C10—C11—N4	−178.77 (18)	C25—C26—C27—C22	0.6 (3)
C11—N4—C12—C13	−0.3 (4)	C23—C22—C27—C26	−0.6 (3)
N4—C12—C13—C14	0.3 (5)	S2—C22—C27—C26	178.14 (16)
C11—C10—C14—C13	−1.1 (4)	C24—C23—C28—O5	173.73 (19)
C9—C10—C14—C13	178.8 (3)	C22—C23—C28—O5	−4.6 (3)
C12—C13—C14—C10	0.4 (5)	C24—C23—C28—O6	−6.2 (3)
C20—C15—C16—C17	−2.6 (3)	C22—C23—C28—O6	175.45 (18)
C21—C15—C16—C17	174.65 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1n···O2	0.88 (1)	2.37 (2)	2.736 (2)	105 (1)
N2—H1n···O2ⁱ	0.88 (1)	2.03 (1)	2.789 (3)	144 (2)
N3—H2n···O1	0.88 (1)	2.37 (2)	2.698 (2)	103 (1)
N3—H2n···O1ⁱⁱ	0.88 (1)	1.97 (1)	2.773 (3)	151 (2)
O4—H1o···N1ⁱⁱⁱ	0.84 (2)	1.83 (2)	2.664 (3)	175 (1)
O6—H2o···N4ⁱⁱ	0.84 (2)	1.80 (2)	2.641 (3)	179 (4)
C2—H2···O3^iv	0.95	2.53	3.220 (3)	129
C3—H3···O1^v	0.95	2.48	3.261 (3)	139
C9—H9b···S1ⁱ	0.99	2.73	3.370 (2)	123

Symmetry codes: (i) −x+2, −y, −z; (ii) −x+1, −y, −z; (iii) x+1, y, z; (iv) x−1, y, z; (v) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₄O₂·C₁₄H₁₀O₄S₂
M_r	576.63
Crystal system, space group	Triclinic, P1
Temperature (K)	98
a, b, c (Å)	10.015 (3), 10.310 (3), 14.795 (4)
α, β, γ (°)	86.910 (16), 78.052 (15), 69.554 (10)
V (Å³)	1400.1 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.50 × 0.19 × 0.10

Data collection
Diffractometer	Rigaku AFC12K/SATURN724 diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.755, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10806, 6365, 5644
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.120, 1.09
No. of reflections	6365
No. of parameters	373
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.41

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1n···O2	0.880 (12)	2.37 (2)	2.736 (2)	105.4 (12)
N2—H1n···O2ⁱ	0.880 (12)	2.026 (10)	2.789 (3)	144.4 (17)
N3—H2n···O1	0.880 (13)	2.37 (2)	2.698 (2)	102.6 (12)
N3—H2n···O1ⁱⁱ	0.880 (13)	1.971 (10)	2.773 (3)	151.0 (18)
O4—H1o···N1ⁱⁱⁱ	0.841 (15)	1.825 (15)	2.664 (3)	175.4 (14)
O6—H2o···N4ⁱⁱ	0.84 (2)	1.80 (2)	2.641 (3)	179 (4)
C2—H2···O3^iv	0.95	2.53	3.220 (3)	129
C3—H3···O1^v	0.95	2.48	3.261 (3)	139
C9—H9b···S1ⁱ	0.99	2.73	3.370 (2)	123

Symmetry codes: (i) −x+2, −y, −z; (ii) −x+1, −y, −z; (iii) x+1, y, z; (iv) x−1, y, z; (v) −x+1, −y+1, −z.

References

Arman, H. D., Kaulgud, T. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2117. Web of Science CSD CrossRef IUCr Journals Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Broker, G. A., Bettens, R. P. A. & Tiekink, E. R. T. (2008). CrystEngComm, 10, 879–887. Web of Science CSD CrossRef CAS Google Scholar
Broker, G. A. & Tiekink, E. R. T. (2007). CrystEngComm, 9, 1096–1109. Web of Science CSD CrossRef CAS Google Scholar
Broker, G. A. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o705. Web of Science CSD CrossRef IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Molecular Structure Corporation & Rigaku (2005). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Poplaukhin, P. & Tiekink, E. R. T. (2010). CrystEngComm, 12, 1302–1306. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 10| October 2010| Pages o2590-o2591

doi:10.1107/S1600536810036494

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,2′-(Disulfanediyl)di­benzoic acid–N,N′-bis­­(3-pyridyl­meth­yl)ethane­di­amide (1/1)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

2,2′-(Disulfanediyl)dibenzoic acid–N,N′-bis(3-pyridylmethyl)ethanediamide (1/1)