2,2'-(Disulfanedi-yl)dibenzoic acid-N,N'-bis-(4-pyridyl-meth-yl)ethane-dithio-amide (1/1).

The asymmetric unit of the title co-crystal, C(14)H(14)N(4)S(2)·C(14)H(10)O(4)S(2), comprises a twisted 2,2'-(disulfanedi-yl)dibenzoic acid mol-ecule [dihedral angle between the benzene rings = 83.53 (14)°] and a U-shaped mol-ecule of N,N'-bis-(4-pyridyl-meth-yl)ethane-dithio-amide in which intra-molecular N-H⋯S hydrogen bonds are observed. Two mol-ecules of each form a centrosymmetric ring, with an extended chair conformation, mediated by carbox-yl-pyridine O-H⋯N hydrogen bonds between the carboxylic acid groups of two 2,2'-(disulfanediyl)dibenzoic acid molecules and pyridine-N atoms of two N,N'-bis(4-pyridylmethyl)ethanedithioamide molecules. The tetra-meric aggregates are linked into a supra-molecular chain along the b axis via amide-carbonyl N-H⋯O hydrogen bonds.

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 ▶).

Experimental

Crystal data

C14H14N4S2·C14H10O4S2

M = 608.75

Monoclinic,

a = 18.502 (5) Å

b = 10.624 (3) Å

c = 15.026 (4) Å

β = 110.235 (5)°

V = 2771.3 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.39 mm−1

T = 98 K

0.38 × 0.26 × 0.10 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer

16758 measured reflections

6348 independent reflections

5349 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.156

S = 1.13

6348 reflections

373 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.30 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/S1600536810036755/hg2714sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036755/hg2714Isup2.hkl

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

C14H14N4S2·C14H10O4S2	F(000) = 1264
Mr = 608.75	Dx = 1.459 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 11634 reflections
a = 18.502 (5) Å	θ = 2.2–40.8°
b = 10.624 (3) Å	µ = 0.39 mm−1
c = 15.026 (4) Å	T = 98 K
β = 110.235 (5)°	Block, red
V = 2771.3 (13) Å3	0.38 × 0.26 × 0.10 mm
Z = 4

Rigaku AFC12K/SATURN724 diffractometer	5349 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.050
graphite	θmax = 27.5°, θmin = 2.3°
ω scans	h = −22→24
16758 measured reflections	k = −13→12
6348 independent reflections	l = −19→12

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.0595P)2 + 1.5417P] where P = (Fo2 + 2Fc2)/3
6348 reflections	(Δ/σ)max = 0.001
373 parameters	Δρmax = 0.40 e Å−3
4 restraints	Δρmin = −0.30 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.14789 (4)	1.09050 (7)	0.26162 (6)	0.0419 (2)
S2	0.38384 (5)	1.05034 (10)	0.43964 (7)	0.0577 (3)
S3	0.28281 (4)	0.41538 (6)	0.47637 (5)	0.03595 (18)
S4	0.23818 (4)	0.28425 (6)	0.54351 (5)	0.03659 (18)
O1	0.36687 (12)	0.57687 (19)	0.40613 (16)	0.0439 (5)
O2	0.45371 (13)	0.7063 (3)	0.50168 (18)	0.0542 (6)
H1o	0.469 (2)	0.707 (4)	0.455 (2)	0.081*
O3	0.18572 (13)	0.1116 (2)	0.63693 (18)	0.0487 (5)
O4	0.06256 (14)	0.06603 (19)	0.61426 (18)	0.0482 (6)
H2o	0.0915 (19)	0.016 (3)	0.655 (2)	0.072*
N1	0.10469 (15)	0.6043 (2)	0.23918 (19)	0.0389 (6)
N2	0.22644 (15)	0.9846 (3)	0.42551 (19)	0.0445 (6)
H1n	0.2727 (10)	0.978 (3)	0.4689 (19)	0.053*
N3	0.30049 (14)	1.2123 (2)	0.3103 (2)	0.0401 (6)
H2n	0.2547 (10)	1.233 (3)	0.271 (2)	0.048*
N4	0.48896 (14)	1.2348 (3)	0.12994 (19)	0.0439 (6)
C1	0.13990 (17)	0.8058 (3)	0.3642 (2)	0.0363 (6)
C2	0.19777 (17)	0.7309 (3)	0.3524 (2)	0.0389 (6)
H2	0.2504	0.7483	0.3872	0.047*
C3	0.17793 (17)	0.6311 (3)	0.2896 (2)	0.0376 (6)
H3	0.2176	0.5801	0.2820	0.045*
C4	0.04915 (17)	0.6752 (3)	0.2516 (2)	0.0389 (6)
H4	−0.0030	0.6554	0.2163	0.047*
C5	0.06427 (16)	0.7753 (3)	0.3131 (2)	0.0367 (6)
H5	0.0233	0.8230	0.3205	0.044*
C6	0.16015 (19)	0.9164 (3)	0.4317 (2)	0.0465 (7)
H6A	0.1155	0.9740	0.4164	0.056*
H6B	0.1717	0.8858	0.4974	0.056*
C7	0.22516 (16)	1.0588 (3)	0.3541 (2)	0.0365 (6)
C8	0.30383 (17)	1.1141 (3)	0.3643 (2)	0.0395 (7)
C9	0.36528 (19)	1.2963 (3)	0.3191 (3)	0.0514 (9)
H9A	0.4025	1.2903	0.3847	0.062*
H9B	0.3459	1.3839	0.3093	0.062*
C10	0.40742 (17)	1.2706 (3)	0.2513 (2)	0.0414 (7)
C11	0.43798 (18)	1.3709 (3)	0.2185 (3)	0.0476 (7)
H11	0.4306	1.4543	0.2365	0.057*
C12	0.47942 (19)	1.3496 (3)	0.1591 (3)	0.0509 (8)
H12	0.5018	1.4192	0.1385	0.061*
C13	0.45899 (17)	1.1392 (3)	0.1596 (2)	0.0447 (7)
H13	0.4657	1.0572	0.1384	0.054*
C14	0.41768 (18)	1.1519 (3)	0.2208 (3)	0.0470 (7)
H14	0.3969	1.0802	0.2411	0.056*
C15	0.35166 (15)	0.6427 (2)	0.5491 (2)	0.0336 (6)
C16	0.29850 (16)	0.5498 (2)	0.5523 (2)	0.0337 (6)
C17	0.25988 (17)	0.5629 (3)	0.6169 (2)	0.0384 (6)
H17	0.2235	0.5011	0.6193	0.046*
C18	0.27440 (19)	0.6650 (3)	0.6771 (2)	0.0460 (7)
H18	0.2473	0.6728	0.7203	0.055*
C19	0.32744 (19)	0.7565 (3)	0.6763 (3)	0.0482 (8)
H19	0.3373	0.8259	0.7187	0.058*
C20	0.36576 (17)	0.7446 (3)	0.6123 (2)	0.0407 (7)
H20	0.4024	0.8067	0.6112	0.049*
C21	0.39214 (16)	0.6382 (3)	0.4790 (2)	0.0352 (6)
C22	0.13608 (16)	0.3115 (3)	0.4988 (2)	0.0346 (6)
C23	0.08651 (17)	0.2328 (2)	0.5271 (2)	0.0351 (6)
C24	0.00720 (18)	0.2556 (3)	0.4900 (2)	0.0418 (7)
H24	−0.0266	0.2019	0.5078	0.050*
C25	−0.02326 (18)	0.3530 (3)	0.4287 (2)	0.0450 (7)
H25	−0.0773	0.3669	0.4047	0.054*
C26	0.02518 (19)	0.4301 (3)	0.4026 (2)	0.0466 (7)
H26	0.0046	0.4987	0.3610	0.056*
C27	0.10406 (17)	0.4090 (3)	0.4363 (2)	0.0415 (7)
H27	0.1367	0.4622	0.4161	0.050*
C28	0.11699 (17)	0.1310 (3)	0.5979 (2)	0.0369 (6)

	U11	U22	U33	U12	U13	U23
S1	0.0356 (4)	0.0497 (4)	0.0434 (5)	−0.0029 (3)	0.0175 (3)	0.0003 (3)
S2	0.0405 (4)	0.0839 (6)	0.0467 (5)	−0.0025 (4)	0.0127 (4)	−0.0042 (5)
S3	0.0454 (4)	0.0380 (4)	0.0333 (4)	−0.0046 (3)	0.0250 (3)	−0.0045 (3)
S4	0.0435 (4)	0.0368 (3)	0.0357 (4)	−0.0001 (3)	0.0215 (3)	0.0020 (3)
O1	0.0499 (12)	0.0498 (12)	0.0446 (13)	−0.0110 (9)	0.0321 (11)	−0.0096 (10)
O2	0.0440 (12)	0.0843 (16)	0.0417 (14)	−0.0211 (11)	0.0244 (11)	−0.0103 (13)
O3	0.0585 (14)	0.0433 (11)	0.0520 (14)	0.0064 (10)	0.0292 (12)	0.0153 (10)
O4	0.0566 (14)	0.0402 (11)	0.0561 (15)	−0.0004 (10)	0.0300 (12)	0.0117 (10)
N1	0.0505 (14)	0.0356 (12)	0.0407 (14)	−0.0035 (10)	0.0285 (12)	−0.0009 (10)
N2	0.0473 (14)	0.0528 (15)	0.0324 (14)	−0.0135 (12)	0.0125 (12)	−0.0055 (12)
N3	0.0408 (13)	0.0452 (13)	0.0427 (15)	−0.0110 (11)	0.0253 (12)	−0.0135 (11)
N4	0.0355 (12)	0.0631 (16)	0.0361 (15)	0.0073 (11)	0.0160 (11)	0.0018 (12)
C1	0.0486 (16)	0.0363 (13)	0.0296 (15)	−0.0040 (12)	0.0205 (13)	0.0023 (11)
C2	0.0376 (14)	0.0440 (15)	0.0368 (17)	0.0005 (12)	0.0152 (13)	0.0100 (12)
C3	0.0442 (15)	0.0341 (13)	0.0431 (17)	0.0045 (11)	0.0262 (14)	0.0100 (12)
C4	0.0417 (15)	0.0393 (14)	0.0399 (17)	−0.0047 (12)	0.0197 (13)	−0.0018 (12)
C5	0.0422 (15)	0.0372 (13)	0.0379 (16)	−0.0005 (11)	0.0231 (13)	−0.0007 (12)
C6	0.0573 (19)	0.0523 (17)	0.0356 (17)	−0.0154 (15)	0.0231 (15)	−0.0088 (14)
C7	0.0423 (15)	0.0377 (14)	0.0346 (16)	−0.0074 (11)	0.0200 (13)	−0.0092 (12)
C8	0.0415 (15)	0.0451 (15)	0.0371 (16)	−0.0088 (12)	0.0202 (13)	−0.0160 (13)
C9	0.0545 (19)	0.0558 (18)	0.058 (2)	−0.0189 (15)	0.0367 (18)	−0.0220 (16)
C10	0.0378 (15)	0.0480 (16)	0.0438 (18)	−0.0066 (12)	0.0210 (14)	−0.0065 (13)
C11	0.0480 (17)	0.0491 (17)	0.051 (2)	0.0005 (14)	0.0241 (16)	−0.0003 (15)
C12	0.0492 (18)	0.0589 (19)	0.052 (2)	0.0012 (15)	0.0273 (17)	0.0020 (16)
C13	0.0417 (16)	0.0509 (17)	0.0427 (18)	0.0026 (13)	0.0160 (14)	−0.0075 (14)
C14	0.0492 (17)	0.0469 (16)	0.051 (2)	−0.0080 (13)	0.0248 (16)	−0.0093 (14)
C15	0.0333 (13)	0.0394 (14)	0.0313 (15)	−0.0002 (11)	0.0154 (12)	−0.0004 (11)
C16	0.0378 (14)	0.0370 (13)	0.0300 (15)	0.0011 (11)	0.0165 (12)	−0.0008 (11)
C17	0.0444 (15)	0.0408 (14)	0.0382 (17)	−0.0022 (12)	0.0246 (14)	−0.0037 (12)
C18	0.0568 (18)	0.0523 (17)	0.0413 (18)	−0.0017 (14)	0.0326 (16)	−0.0079 (14)
C19	0.0574 (19)	0.0482 (17)	0.0459 (19)	−0.0053 (14)	0.0267 (16)	−0.0164 (14)
C20	0.0425 (15)	0.0432 (15)	0.0402 (17)	−0.0062 (12)	0.0190 (14)	−0.0060 (13)
C21	0.0363 (14)	0.0389 (14)	0.0347 (16)	0.0012 (11)	0.0178 (12)	0.0008 (12)
C22	0.0418 (14)	0.0375 (13)	0.0291 (15)	−0.0049 (11)	0.0182 (12)	−0.0040 (11)
C23	0.0470 (15)	0.0350 (13)	0.0279 (14)	−0.0040 (11)	0.0187 (12)	−0.0023 (11)
C24	0.0481 (16)	0.0431 (15)	0.0391 (17)	−0.0109 (13)	0.0213 (14)	−0.0024 (13)
C25	0.0416 (16)	0.0552 (18)	0.0354 (17)	−0.0042 (13)	0.0099 (14)	0.0021 (14)
C26	0.0497 (17)	0.0499 (17)	0.0370 (18)	−0.0036 (14)	0.0108 (14)	0.0088 (13)
C27	0.0449 (16)	0.0456 (16)	0.0359 (17)	−0.0068 (13)	0.0166 (14)	0.0065 (13)
C28	0.0494 (17)	0.0323 (13)	0.0373 (16)	−0.0010 (12)	0.0255 (14)	−0.0020 (11)

S1—C7	1.648 (3)	C9—C10	1.506 (4)
S2—C8	1.665 (3)	C9—H9A	0.9900
S3—C16	1.788 (3)	C9—H9B	0.9900
S3—S4	2.0535 (10)	C10—C11	1.375 (4)
S4—C22	1.796 (3)	C10—C14	1.378 (4)
O1—C21	1.219 (4)	C11—C12	1.381 (4)
O2—C21	1.292 (3)	C11—H11	0.9500
O2—H1o	0.84 (3)	C12—H12	0.9500
O3—C28	1.220 (4)	C13—C14	1.390 (4)
O4—C28	1.312 (3)	C13—H13	0.9500
O4—H2o	0.85 (3)	C14—H14	0.9500
N1—C3	1.334 (4)	C15—C20	1.404 (4)
N1—C4	1.338 (4)	C15—C16	1.406 (4)
N2—C7	1.325 (4)	C15—C21	1.490 (4)
N2—C6	1.455 (4)	C16—C17	1.397 (4)
N2—H1n	0.88 (3)	C17—C18	1.379 (4)
N3—C8	1.310 (4)	C17—H17	0.9500
N3—C9	1.464 (4)	C18—C19	1.384 (4)
N3—H2n	0.88 (3)	C18—H18	0.9500
N4—C13	1.308 (4)	C19—C20	1.384 (4)
N4—C12	1.329 (4)	C19—H19	0.9500
C1—C5	1.382 (4)	C20—H20	0.9500
C1—C2	1.394 (4)	C22—C27	1.386 (4)
C1—C6	1.512 (4)	C22—C23	1.411 (4)
C2—C3	1.382 (4)	C23—C24	1.399 (4)
C2—H2	0.9500	C23—C28	1.485 (4)
C3—H3	0.9500	C24—C25	1.371 (4)
C4—C5	1.373 (4)	C24—H24	0.9500
C4—H4	0.9500	C25—C26	1.367 (4)
C5—H5	0.9500	C25—H25	0.9500
C6—H6A	0.9900	C26—C27	1.388 (4)
C6—H6B	0.9900	C26—H26	0.9500
C7—C8	1.527 (4)	C27—H27	0.9500
C16—S3—S4	103.44 (10)	N4—C12—C11	122.0 (3)
C22—S4—S3	104.86 (10)	N4—C12—H12	119.0
C21—O2—H1O	108 (3)	C11—C12—H12	119.0
C28—O4—H2O	98 (3)	N4—C13—C14	123.0 (3)
C3—N1—C4	118.6 (3)	N4—C13—H13	118.5
C7—N2—C6	124.7 (3)	C14—C13—H13	118.5
C7—N2—H1N	113 (2)	C10—C14—C13	118.7 (3)
C6—N2—H1N	122 (2)	C10—C14—H14	120.6
C8—N3—C9	124.6 (3)	C13—C14—H14	120.6
C8—N3—H2N	117 (2)	C20—C15—C16	119.1 (3)
C9—N3—H2N	118 (2)	C20—C15—C21	118.8 (2)
C13—N4—C12	118.7 (3)	C16—C15—C21	122.0 (2)
C5—C1—C2	118.1 (3)	C17—C16—C15	119.1 (3)
C5—C1—C6	121.5 (3)	C17—C16—S3	120.9 (2)
C2—C1—C6	120.4 (3)	C15—C16—S3	120.0 (2)
C3—C2—C1	119.4 (3)	C18—C17—C16	120.3 (3)
C3—C2—H2	120.3	C18—C17—H17	119.9
C1—C2—H2	120.3	C16—C17—H17	119.9
N1—C3—C2	121.9 (3)	C17—C18—C19	121.6 (3)
N1—C3—H3	119.0	C17—C18—H18	119.2
C2—C3—H3	119.0	C19—C18—H18	119.2
N1—C4—C5	122.9 (3)	C20—C19—C18	118.5 (3)
N1—C4—H4	118.6	C20—C19—H19	120.7
C5—C4—H4	118.6	C18—C19—H19	120.7
C4—C5—C1	119.1 (3)	C19—C20—C15	121.4 (3)
C4—C5—H5	120.4	C19—C20—H20	119.3
C1—C5—H5	120.4	C15—C20—H20	119.3
N2—C6—C1	111.3 (2)	O1—C21—O2	124.4 (3)
N2—C6—H6A	109.4	O1—C21—C15	121.5 (3)
C1—C6—H6A	109.4	O2—C21—C15	114.1 (3)
N2—C6—H6B	109.4	C27—C22—C23	118.5 (3)
C1—C6—H6B	109.4	C27—C22—S4	121.5 (2)
H6A—C6—H6B	108.0	C23—C22—S4	120.1 (2)
N2—C7—C8	113.5 (3)	C24—C23—C22	118.6 (3)
N2—C7—S1	124.9 (2)	C24—C23—C28	119.9 (2)
C8—C7—S1	121.6 (2)	C22—C23—C28	121.5 (3)
N3—C8—C7	113.9 (3)	C25—C24—C23	122.0 (3)
N3—C8—S2	125.8 (2)	C25—C24—H24	119.0
C7—C8—S2	120.3 (2)	C23—C24—H24	119.0
N3—C9—C10	115.3 (3)	C26—C25—C24	119.1 (3)
N3—C9—H9A	108.4	C26—C25—H25	120.4
C10—C9—H9A	108.4	C24—C25—H25	120.4
N3—C9—H9B	108.4	C25—C26—C27	120.7 (3)
C10—C9—H9B	108.4	C25—C26—H26	119.7
H9A—C9—H9B	107.5	C27—C26—H26	119.7
C11—C10—C14	117.9 (3)	C22—C27—C26	121.1 (3)
C11—C10—C9	118.4 (3)	C22—C27—H27	119.4
C14—C10—C9	123.7 (3)	C26—C27—H27	119.4
C10—C11—C12	119.6 (3)	O3—C28—O4	124.2 (3)
C10—C11—H11	120.2	O3—C28—C23	122.8 (3)
C12—C11—H11	120.2	O4—C28—C23	113.0 (3)
C16—S3—S4—C22	88.06 (13)	C20—C15—C16—S3	−177.1 (2)
C5—C1—C2—C3	1.1 (4)	C21—C15—C16—S3	4.5 (4)
C6—C1—C2—C3	−179.4 (3)	S4—S3—C16—C17	−20.3 (3)
C4—N1—C3—C2	−1.3 (4)	S4—S3—C16—C15	158.2 (2)
C1—C2—C3—N1	0.3 (4)	C15—C16—C17—C18	−0.6 (4)
C3—N1—C4—C5	0.8 (4)	S3—C16—C17—C18	177.9 (2)
N1—C4—C5—C1	0.6 (4)	C16—C17—C18—C19	−0.5 (5)
C2—C1—C5—C4	−1.5 (4)	C17—C18—C19—C20	0.7 (5)
C6—C1—C5—C4	178.9 (3)	C18—C19—C20—C15	0.1 (5)
C7—N2—C6—C1	73.4 (4)	C16—C15—C20—C19	−1.2 (5)
C5—C1—C6—N2	−139.7 (3)	C21—C15—C20—C19	177.3 (3)
C2—C1—C6—N2	40.8 (4)	C20—C15—C21—O1	−157.7 (3)
C6—N2—C7—C8	−177.5 (3)	C16—C15—C21—O1	20.7 (4)
C6—N2—C7—S1	2.1 (4)	C20—C15—C21—O2	20.7 (4)
C9—N3—C8—C7	168.0 (2)	C16—C15—C21—O2	−160.9 (3)
C9—N3—C8—S2	−11.6 (4)	S3—S4—C22—C27	−3.0 (3)
N2—C7—C8—N3	−162.1 (3)	S3—S4—C22—C23	177.0 (2)
S1—C7—C8—N3	18.3 (3)	C27—C22—C23—C24	0.8 (4)
N2—C7—C8—S2	17.4 (3)	S4—C22—C23—C24	−179.2 (2)
S1—C7—C8—S2	−162.20 (17)	C27—C22—C23—C28	−176.5 (3)
C8—N3—C9—C10	98.3 (4)	S4—C22—C23—C28	3.5 (4)
N3—C9—C10—C11	146.4 (3)	C22—C23—C24—C25	−1.2 (4)
N3—C9—C10—C14	−34.1 (5)	C28—C23—C24—C25	176.1 (3)
C14—C10—C11—C12	−2.0 (5)	C23—C24—C25—C26	0.3 (5)
C9—C10—C11—C12	177.6 (3)	C24—C25—C26—C27	1.1 (5)
C13—N4—C12—C11	−1.0 (5)	C23—C22—C27—C26	0.6 (5)
C10—C11—C12—N4	2.1 (5)	S4—C22—C27—C26	−179.5 (3)
C12—N4—C13—C14	−0.2 (5)	C25—C26—C27—C22	−1.5 (5)
C11—C10—C14—C13	0.8 (5)	C24—C23—C28—O3	−175.5 (3)
C9—C10—C14—C13	−178.7 (3)	C22—C23—C28—O3	1.7 (4)
N4—C13—C14—C10	0.3 (5)	C24—C23—C28—O4	3.9 (4)
C20—C15—C16—C17	1.4 (4)	C22—C23—C28—O4	−178.8 (3)
C21—C15—C16—C17	−177.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1o···N4i	0.84 (3)	1.73 (3)	2.565 (4)	168 (4)
O4—H2o···N1ii	0.85 (3)	1.76 (3)	2.529 (3)	151 (4)
N2—H1n···S2	0.88 (2)	2.37 (2)	2.930 (3)	121 (2)
N3—H2n···O3iii	0.88 (3)	2.58 (3)	3.312 (4)	142 (2)
N3—H2n···S1	0.88 (3)	2.45 (3)	2.959 (3)	117 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1o⋯N4i	0.84 (3)	1.73 (3)	2.565 (4)	168 (4)
O4—H2o⋯N1ii	0.85 (3)	1.76 (3)	2.529 (3)	151 (4)
N2—H1n⋯S2	0.88 (2)	2.37 (2)	2.930 (3)	121 (2)
N3—H2n⋯O3iii	0.88 (3)	2.58 (3)	3.312 (4)	142 (2)
N3—H2n⋯S1	0.88 (3)	2.45 (3)	2.959 (3)	117 (2)

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