2,2'-(Disulfanediyl)dibenzoic acid-N,N'-bis-(3-pyridyl-meth-yl)ethane-diamide (1/1).

The asymmetric unit of the title cocrystal, C(14)H(14)N(4)O(2)·C(14)H(10)O(4)S(2), comprises a twisted 2,2'-(disulfanediyl)dibenzoic acid mol-ecule [dihedral angle between the benzene rings = 76.35 (10)°] and a U-shaped N,N'-bis-(3-pyridyl-meth-yl)ethane-diamide mol-ecule 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 supra-molecular tapes propagating along the a axis via centrosymmetric eight-membered amide {⋯OCNH}(2) synthons. Intra-molecular N-H⋯O hydrogen bonds are observed. The 2,2'-(disulfanediyl)dibenzoic acid mol-ecules form carbox-yl-pyridine O-H⋯N hydrogen bonds, bridging a pyridine residue below the plane of the tape and one above the plane with two inter-vening N,N'-bis-(3-pyridyl-meth-yl)ethane-diamide mol-ecules. The supra-molecular chains are consolidated in the crystal packing by C-H⋯O contacts. An inter-molecular C-H⋯S inter-action 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 = 576.63

Triclinic,

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[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.120

S = 1.09

6365 reflections

373 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.41 e Å−3

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 ▶).

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

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

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

C14H14N4O2·C14H10O4S2	Z = 2
Mr = 576.63	F(000) = 600
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0472P)2 + 0.7689P] where P = (Fo2 + 2Fc2)/3
6365 reflections	(Δ/σ)max = 0.001
373 parameters	Δρmax = 0.36 e Å−3
4 restraints	Δρmin = −0.41 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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···O3iv	0.95	2.53	3.220 (3)	129
C3—H3···O1v	0.95	2.48	3.261 (3)	139
C9—H9b···S1i	0.99	2.73	3.370 (2)	123

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⋯O3iv	0.95	2.53	3.220 (3)	129
C3—H3⋯O1v	0.95	2.48	3.261 (3)	139
C9—H9b⋯S1i	0.99	2.73	3.370 (2)	123

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