An amide cyclo-phane.

The title compound, 8,18-dithia-2,6-diaza-13(1,4)-piperidina-1(1,2),4(1,3),7(1,2)-tribenzenaoctadecaphane-10,15-diyne-3,6-dione, C32H30N4O2S2, is composed of a relatively planar bis-(2-mercaptophen-yl)isophthalamide unit linked to a bridging 1,4-di(but-2-yn-1-yl)piperazine unit, forming a macrocycle. The isophthalamide ring is inclined to the outer mercaptophenyl rings by 8.18 (11) and 5.59 (10)°, while these two rings are inclined to one another by 9.10 (12)°. The piperazine ring adopts a chair conformation. There are two intra-molecular N-H⋯S hydrogen bonds generating S(5) ring motifs. In the crystal, mol-ecules are linked via C-H⋯S and C-H⋯O hydrogen bonds, forming slabs lying parallel to (001). An O atom in the isophthalamide group is disordered over two positions with an occupancy ratio of 0.41 (6):0.59 (6).

Related literature

For the biological activity of piperazine derivatives, see: Fun et al. (2011 ▶); Kavitha et al. (2013 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C32H30N4O2S2

M = 566.72

Monoclinic,

a = 23.0760 (5) Å

b = 9.9380 (3) Å

c = 27.0341 (7) Å

β = 108.428 (2)°

V = 5881.8 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.380, T max = 0.745

27488 measured reflections

7294 independent reflections

4040 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.117

S = 1.01

7294 reflections

377 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814015621/su2737sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814015621/su2737Isup2.hkl

CCDC reference: 1012131

Additional supporting information: crystallographic information; 3D view; checkCIF report

C32H30N4O2S2	F(000) = 2384
Mr = 566.72	Dx = 1.280 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7294 reflections
a = 23.0760 (5) Å	θ = 1.6–28.3°
b = 9.9380 (3) Å	µ = 0.22 mm−1
c = 27.0341 (7) Å	T = 293 K
β = 108.428 (2)°	Block, colourless
V = 5881.8 (3) Å3	0.30 × 0.25 × 0.20 mm
Z = 8

Bruker SMART APEXII area-detector diffractometer	7294 independent reflections
Radiation source: fine-focus sealed tube	4040 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω and φ scans	θmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −30→30
Tmin = 0.380, Tmax = 0.745	k = −13→13
27488 measured reflections	l = −34→35

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0438P)2 + 2.0132P] where P = (Fo2 + 2Fc2)/3
7294 reflections	(Δ/σ)max = 0.001
377 parameters	Δρmax = 0.20 e Å−3
2 restraints	Δρmin = −0.23 e Å−3

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 > 2sigma(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	Occ. (<1)
S1	0.41059 (2)	0.21672 (6)	1.01916 (2)	0.06329 (16)
S2	0.58670 (2)	0.64936 (6)	0.76454 (2)	0.06810 (17)
O1	0.47117 (6)	0.54558 (14)	0.89655 (5)	0.0671 (4)
O2A	0.7513 (7)	0.440 (3)	0.9253 (10)	0.108 (5)	0.41 (6)
O2B	0.7544 (4)	0.482 (3)	0.9314 (5)	0.115 (4)	0.59 (6)
N1	0.57053 (7)	0.08419 (16)	0.81521 (6)	0.0584 (4)
N2	0.45152 (7)	0.37111 (18)	0.94254 (7)	0.0634 (5)
H2A	0.4674 (9)	0.3112 (19)	0.9642 (8)	0.076*
N3	0.67548 (7)	0.5408 (2)	0.86248 (7)	0.0650 (5)
H3A	0.6377 (7)	0.544 (2)	0.8508 (8)	0.078*
N4	0.50216 (7)	−0.03836 (15)	0.87441 (6)	0.0541 (4)
C1	0.66745 (9)	0.6485 (2)	0.78117 (9)	0.0625 (5)
C2	0.69417 (11)	0.7074 (3)	0.74746 (11)	0.0866 (7)
H2	0.6695	0.7458	0.7166	0.104*
C3	0.75672 (13)	0.7100 (3)	0.75881 (13)	0.1039 (9)
H3	0.7744	0.7507	0.7361	0.125*
C4	0.79235 (11)	0.6519 (3)	0.80401 (13)	0.0995 (9)
H4	0.8346	0.6519	0.8115	0.119*
C5	0.76738 (10)	0.5931 (3)	0.83875 (10)	0.0825 (7)
H5	0.7925	0.5540	0.8693	0.099*
C6	0.70420 (8)	0.5926 (2)	0.82788 (9)	0.0618 (5)
C7	0.69931 (9)	0.4820 (2)	0.90941 (9)	0.0660 (6)
C8	0.65534 (8)	0.43753 (18)	0.93660 (8)	0.0536 (5)
C9	0.67931 (9)	0.3618 (2)	0.98150 (9)	0.0657 (6)
H9	0.7211	0.3448	0.9937	0.079*
C10	0.64258 (10)	0.3116 (2)	1.00816 (9)	0.0709 (6)
H10	0.6594	0.2596	1.0379	0.085*
C11	0.58065 (9)	0.3380 (2)	0.99107 (8)	0.0622 (5)
H11	0.5558	0.3034	1.0092	0.075*
C12	0.55554 (8)	0.41599 (17)	0.94693 (7)	0.0484 (4)
C13	0.59316 (8)	0.46595 (18)	0.92026 (7)	0.0497 (4)
H13	0.5766	0.5194	0.8909	0.060*
C14	0.48890 (8)	0.45151 (19)	0.92630 (7)	0.0517 (4)
C15	0.38767 (8)	0.3776 (2)	0.93183 (8)	0.0578 (5)
C16	0.34978 (10)	0.4520 (2)	0.89092 (9)	0.0770 (7)
H16	0.3663	0.5021	0.8696	0.092*
C17	0.28782 (11)	0.4512 (3)	0.88210 (11)	0.0917 (8)
H17	0.2625	0.5006	0.8545	0.110*
C18	0.26290 (11)	0.3792 (3)	0.91326 (12)	0.0942 (8)
H18	0.2209	0.3793	0.9068	0.113*
C19	0.30033 (10)	0.3061 (2)	0.95441 (10)	0.0763 (6)
H19	0.2834	0.2577	0.9759	0.092*
C20	0.36274 (8)	0.3043 (2)	0.96403 (8)	0.0575 (5)
C21	0.39422 (9)	0.0419 (2)	1.00030 (8)	0.0623 (5)
H21A	0.4140	−0.0144	1.0302	0.075*
H21B	0.3505	0.0277	0.9915	0.075*
C22	0.41344 (9)	−0.0032 (2)	0.95642 (9)	0.0573 (5)
C23	0.42885 (9)	−0.0462 (2)	0.92174 (9)	0.0590 (5)
C24	0.44899 (10)	−0.1063 (2)	0.88040 (8)	0.0651 (5)
H24A	0.4587	−0.2003	0.8884	0.078*
H24B	0.4158	−0.1020	0.8477	0.078*
C25	0.53008 (10)	−0.1175 (2)	0.84244 (9)	0.0685 (6)
H25A	0.5012	−0.1287	0.8077	0.082*
H25B	0.5408	−0.2061	0.8577	0.082*
C26	0.58637 (10)	−0.0470 (2)	0.83922 (9)	0.0695 (6)
H26A	0.6153	−0.0366	0.8739	0.083*
H26B	0.6056	−0.1007	0.8188	0.083*
C27	0.48647 (9)	0.0944 (2)	0.85116 (9)	0.0638 (5)
H27A	0.4686	0.1480	0.8726	0.077*
H27B	0.4564	0.0854	0.8169	0.077*
C28	0.54223 (9)	0.1640 (2)	0.84643 (9)	0.0648 (6)
H28A	0.5309	0.2514	0.8303	0.078*
H28B	0.5713	0.1779	0.8809	0.078*
C29	0.62297 (9)	0.1516 (2)	0.80817 (9)	0.0725 (6)
H29A	0.6431	0.0916	0.7905	0.087*
H29B	0.6518	0.1733	0.8420	0.087*
C30	0.60525 (10)	0.2749 (3)	0.77769 (9)	0.0668 (6)
C31	0.58869 (9)	0.3744 (3)	0.75342 (9)	0.0651 (6)
C32	0.56795 (10)	0.4989 (2)	0.72467 (8)	0.0748 (6)
H32A	0.5240	0.4946	0.7086	0.090*
H32B	0.5861	0.5057	0.6969	0.090*

	U11	U22	U33	U12	U13	U23
S1	0.0621 (3)	0.0687 (3)	0.0562 (3)	−0.0058 (3)	0.0146 (2)	0.0010 (3)
S2	0.0538 (3)	0.0752 (4)	0.0786 (4)	0.0148 (3)	0.0256 (3)	0.0111 (3)
O1	0.0593 (8)	0.0693 (9)	0.0674 (9)	0.0087 (7)	0.0123 (7)	0.0201 (8)
O2A	0.035 (5)	0.131 (11)	0.160 (10)	0.023 (6)	0.032 (6)	0.061 (7)
O2B	0.050 (3)	0.167 (9)	0.104 (5)	−0.038 (5)	−0.010 (3)	0.051 (5)
N1	0.0518 (9)	0.0574 (10)	0.0665 (11)	0.0045 (8)	0.0195 (8)	−0.0074 (8)
N2	0.0491 (9)	0.0689 (12)	0.0744 (12)	0.0115 (8)	0.0229 (9)	0.0232 (9)
N3	0.0378 (8)	0.0918 (13)	0.0638 (11)	−0.0020 (9)	0.0140 (8)	0.0025 (10)
N4	0.0568 (9)	0.0477 (9)	0.0555 (10)	0.0057 (7)	0.0146 (8)	−0.0030 (8)
C1	0.0536 (11)	0.0650 (13)	0.0762 (15)	0.0019 (10)	0.0308 (11)	−0.0003 (11)
C2	0.0780 (16)	0.1015 (19)	0.0924 (18)	0.0038 (14)	0.0444 (14)	0.0149 (15)
C3	0.0777 (18)	0.134 (3)	0.118 (2)	−0.0075 (17)	0.0565 (18)	0.016 (2)
C4	0.0535 (14)	0.137 (3)	0.119 (2)	−0.0141 (15)	0.0430 (16)	−0.006 (2)
C5	0.0482 (12)	0.114 (2)	0.0867 (17)	−0.0087 (13)	0.0239 (12)	−0.0074 (15)
C6	0.0466 (11)	0.0719 (13)	0.0715 (14)	−0.0064 (10)	0.0250 (10)	−0.0109 (11)
C7	0.0454 (11)	0.0712 (14)	0.0750 (15)	−0.0064 (11)	0.0098 (11)	0.0034 (12)
C8	0.0461 (10)	0.0476 (10)	0.0620 (12)	−0.0014 (8)	0.0101 (9)	−0.0022 (9)
C9	0.0483 (11)	0.0615 (13)	0.0798 (15)	0.0079 (10)	0.0094 (10)	0.0108 (11)
C10	0.0644 (13)	0.0672 (14)	0.0718 (15)	0.0120 (11)	0.0082 (11)	0.0211 (11)
C11	0.0606 (12)	0.0617 (12)	0.0640 (13)	0.0072 (10)	0.0194 (10)	0.0130 (10)
C12	0.0501 (10)	0.0419 (10)	0.0515 (11)	0.0050 (8)	0.0138 (9)	−0.0006 (8)
C13	0.0491 (10)	0.0452 (10)	0.0500 (11)	−0.0003 (8)	0.0087 (8)	−0.0014 (8)
C14	0.0541 (11)	0.0515 (11)	0.0490 (11)	0.0065 (9)	0.0156 (9)	−0.0003 (9)
C15	0.0459 (10)	0.0674 (13)	0.0605 (12)	0.0093 (9)	0.0176 (9)	0.0024 (10)
C16	0.0611 (13)	0.0964 (17)	0.0723 (15)	0.0196 (12)	0.0192 (11)	0.0208 (13)
C17	0.0590 (14)	0.116 (2)	0.0890 (18)	0.0270 (14)	0.0080 (13)	0.0195 (17)
C18	0.0475 (13)	0.118 (2)	0.112 (2)	0.0165 (14)	0.0184 (14)	0.0008 (18)
C19	0.0549 (13)	0.0916 (17)	0.0885 (17)	0.0025 (12)	0.0313 (12)	−0.0010 (14)
C20	0.0491 (10)	0.0642 (12)	0.0596 (12)	0.0033 (9)	0.0176 (9)	−0.0051 (10)
C21	0.0569 (12)	0.0657 (13)	0.0643 (13)	−0.0067 (10)	0.0192 (10)	0.0061 (11)
C22	0.0478 (11)	0.0565 (12)	0.0624 (13)	−0.0020 (9)	0.0101 (10)	0.0099 (10)
C23	0.0534 (11)	0.0564 (12)	0.0627 (14)	−0.0017 (9)	0.0117 (10)	0.0056 (11)
C24	0.0688 (13)	0.0605 (13)	0.0627 (13)	−0.0048 (11)	0.0159 (11)	−0.0036 (11)
C25	0.0812 (15)	0.0525 (12)	0.0730 (15)	0.0038 (11)	0.0259 (12)	−0.0107 (11)
C26	0.0676 (13)	0.0595 (13)	0.0838 (16)	0.0143 (11)	0.0274 (12)	−0.0113 (12)
C27	0.0598 (12)	0.0596 (12)	0.0746 (14)	0.0140 (10)	0.0249 (11)	0.0068 (11)
C28	0.0679 (13)	0.0508 (11)	0.0794 (15)	0.0084 (10)	0.0287 (11)	−0.0017 (11)
C29	0.0562 (12)	0.0752 (15)	0.0877 (17)	0.0028 (11)	0.0252 (12)	−0.0067 (13)
C30	0.0542 (12)	0.0773 (16)	0.0728 (15)	−0.0072 (12)	0.0257 (11)	−0.0155 (13)
C31	0.0503 (12)	0.0834 (17)	0.0638 (14)	−0.0069 (12)	0.0213 (10)	−0.0138 (13)
C32	0.0618 (13)	0.1047 (18)	0.0559 (13)	−0.0025 (12)	0.0157 (11)	0.0029 (13)

S1—C20	1.777 (2)	C12—C13	1.384 (3)
S1—C21	1.817 (2)	C12—C14	1.503 (2)
S2—C1	1.773 (2)	C13—H13	0.9300
S2—C32	1.814 (2)	C15—C16	1.387 (3)
O1—C14	1.217 (2)	C15—C20	1.391 (3)
O2A—C7	1.215 (11)	C16—C17	1.373 (3)
O2B—C7	1.222 (9)	C16—H16	0.9300
N1—C29	1.448 (3)	C17—C18	1.363 (4)
N1—C26	1.451 (3)	C17—H17	0.9300
N1—C28	1.454 (2)	C18—C19	1.380 (3)
N2—C14	1.347 (2)	C18—H18	0.9300
N2—C15	1.411 (2)	C19—C20	1.380 (3)
N2—H2A	0.833 (15)	C19—H19	0.9300
N3—C7	1.346 (3)	C21—C22	1.462 (3)
N3—C6	1.404 (3)	C21—H21A	0.9700
N3—H3A	0.828 (15)	C21—H21B	0.9700
N4—C24	1.454 (3)	C22—C23	1.183 (3)
N4—C27	1.457 (2)	C23—C24	1.466 (3)
N4—C25	1.461 (2)	C24—H24A	0.9700
C1—C2	1.382 (3)	C24—H24B	0.9700
C1—C6	1.395 (3)	C25—C26	1.503 (3)
C2—C3	1.378 (3)	C25—H25A	0.9700
C2—H2	0.9300	C25—H25B	0.9700
C3—C4	1.367 (4)	C26—H26A	0.9700
C3—H3	0.9300	C26—H26B	0.9700
C4—C5	1.378 (4)	C27—C28	1.502 (3)
C4—H4	0.9300	C27—H27A	0.9700
C5—C6	1.393 (3)	C27—H27B	0.9700
C5—H5	0.9300	C28—H28A	0.9700
C7—C8	1.496 (3)	C28—H28B	0.9700
C8—C9	1.386 (3)	C29—C30	1.461 (3)
C8—C13	1.390 (2)	C29—H29A	0.9700
C9—C10	1.369 (3)	C29—H29B	0.9700
C9—H9	0.9300	C30—C31	1.181 (3)
C10—C11	1.381 (3)	C31—C32	1.459 (3)
C10—H10	0.9300	C32—H32A	0.9700
C11—C12	1.387 (3)	C32—H32B	0.9700
C11—H11	0.9300
C20—S1—C21	102.37 (10)	C18—C17—C16	121.0 (2)
C1—S2—C32	100.43 (10)	C18—C17—H17	119.5
C29—N1—C26	111.83 (16)	C16—C17—H17	119.5
C29—N1—C28	111.80 (16)	C17—C18—C19	119.7 (2)
C26—N1—C28	109.05 (16)	C17—C18—H18	120.1
C14—N2—C15	129.86 (17)	C19—C18—H18	120.1
C14—N2—H2A	117.9 (15)	C18—C19—C20	120.6 (2)
C15—N2—H2A	112.1 (15)	C18—C19—H19	119.7
C7—N3—C6	130.45 (17)	C20—C19—H19	119.7
C7—N3—H3A	116.3 (16)	C19—C20—C15	119.24 (19)
C6—N3—H3A	113.1 (16)	C19—C20—S1	119.93 (17)
C24—N4—C27	111.41 (15)	C15—C20—S1	120.74 (14)
C24—N4—C25	111.20 (15)	C22—C21—S1	115.54 (14)
C27—N4—C25	109.16 (16)	C22—C21—H21A	108.4
C2—C1—C6	119.7 (2)	S1—C21—H21A	108.4
C2—C1—S2	118.89 (18)	C22—C21—H21B	108.4
C6—C1—S2	121.39 (15)	S1—C21—H21B	108.4
C3—C2—C1	121.1 (3)	H21A—C21—H21B	107.5
C3—C2—H2	119.5	C23—C22—C21	176.6 (2)
C1—C2—H2	119.5	C22—C23—C24	176.9 (2)
C4—C3—C2	118.9 (2)	N4—C24—C23	112.22 (16)
C4—C3—H3	120.6	N4—C24—H24A	109.2
C2—C3—H3	120.6	C23—C24—H24A	109.2
C3—C4—C5	121.7 (2)	N4—C24—H24B	109.2
C3—C4—H4	119.1	C23—C24—H24B	109.2
C5—C4—H4	119.1	H24A—C24—H24B	107.9
C4—C5—C6	119.5 (2)	N4—C25—C26	109.52 (16)
C4—C5—H5	120.2	N4—C25—H25A	109.8
C6—C5—H5	120.2	C26—C25—H25A	109.8
C5—C6—C1	119.1 (2)	N4—C25—H25B	109.8
C5—C6—N3	122.9 (2)	C26—C25—H25B	109.8
C1—C6—N3	117.99 (17)	H25A—C25—H25B	108.2
O2A—C7—N3	123.2 (9)	N1—C26—C25	110.17 (17)
O2B—C7—N3	120.8 (7)	N1—C26—H26A	109.6
O2A—C7—C8	118.2 (9)	C25—C26—H26A	109.6
O2B—C7—C8	121.5 (6)	N1—C26—H26B	109.6
N3—C7—C8	116.93 (17)	C25—C26—H26B	109.6
C9—C8—C13	118.33 (18)	H26A—C26—H26B	108.1
C9—C8—C7	116.48 (17)	N4—C27—C28	110.57 (16)
C13—C8—C7	125.19 (18)	N4—C27—H27A	109.5
C10—C9—C8	121.13 (19)	C28—C27—H27A	109.5
C10—C9—H9	119.4	N4—C27—H27B	109.5
C8—C9—H9	119.4	C28—C27—H27B	109.5
C9—C10—C11	120.15 (19)	H27A—C27—H27B	108.1
C9—C10—H10	119.9	N1—C28—C27	110.61 (17)
C11—C10—H10	119.9	N1—C28—H28A	109.5
C10—C11—C12	120.04 (19)	C27—C28—H28A	109.5
C10—C11—H11	120.0	N1—C28—H28B	109.5
C12—C11—H11	120.0	C27—C28—H28B	109.5
C13—C12—C11	119.24 (17)	H28A—C28—H28B	108.1
C13—C12—C14	117.33 (16)	N1—C29—C30	111.46 (17)
C11—C12—C14	123.43 (17)	N1—C29—H29A	109.3
C12—C13—C8	121.06 (17)	C30—C29—H29A	109.3
C12—C13—H13	119.5	N1—C29—H29B	109.3
C8—C13—H13	119.5	C30—C29—H29B	109.3
O1—C14—N2	123.71 (18)	H29A—C29—H29B	108.0
O1—C14—C12	121.12 (18)	C31—C30—C29	177.3 (2)
N2—C14—C12	115.16 (16)	C30—C31—C32	178.5 (2)
C16—C15—C20	119.81 (18)	C31—C32—S2	113.96 (15)
C16—C15—N2	122.85 (19)	C31—C32—H32A	108.8
C20—C15—N2	117.34 (17)	S2—C32—H32A	108.8
C17—C16—C15	119.7 (2)	C31—C32—H32B	108.8
C17—C16—H16	120.2	S2—C32—H32B	108.8
C15—C16—H16	120.2	H32A—C32—H32B	107.7
C32—S2—C1—C2	86.2 (2)	C13—C12—C14—O1	−18.3 (3)
C32—S2—C1—C6	−95.30 (19)	C11—C12—C14—O1	160.92 (19)
C6—C1—C2—C3	1.0 (4)	C13—C12—C14—N2	160.74 (17)
S2—C1—C2—C3	179.6 (2)	C11—C12—C14—N2	−20.0 (3)
C1—C2—C3—C4	0.7 (4)	C14—N2—C15—C16	17.0 (3)
C2—C3—C4—C5	−1.2 (5)	C14—N2—C15—C20	−163.6 (2)
C3—C4—C5—C6	−0.1 (4)	C20—C15—C16—C17	−0.8 (3)
C4—C5—C6—C1	1.8 (4)	N2—C15—C16—C17	178.5 (2)
C4—C5—C6—N3	−176.7 (2)	C15—C16—C17—C18	0.5 (4)
C2—C1—C6—C5	−2.2 (3)	C16—C17—C18—C19	0.2 (4)
S2—C1—C6—C5	179.22 (17)	C17—C18—C19—C20	−0.6 (4)
C2—C1—C6—N3	176.3 (2)	C18—C19—C20—C15	0.3 (3)
S2—C1—C6—N3	−2.2 (3)	C18—C19—C20—S1	176.77 (19)
C7—N3—C6—C5	−1.6 (4)	C16—C15—C20—C19	0.4 (3)
C7—N3—C6—C1	179.9 (2)	N2—C15—C20—C19	−178.96 (19)
C6—N3—C7—O2A	−15 (2)	C16—C15—C20—S1	−176.02 (17)
C6—N3—C7—O2B	9.3 (15)	N2—C15—C20—S1	4.6 (3)
C6—N3—C7—C8	180.0 (2)	C21—S1—C20—C19	72.16 (19)
O2A—C7—C8—C9	6 (2)	C21—S1—C20—C15	−111.40 (17)
O2B—C7—C8—C9	−17.5 (15)	C20—S1—C21—C22	66.21 (17)
N3—C7—C8—C9	171.90 (19)	C27—N4—C24—C23	−71.5 (2)
O2A—C7—C8—C13	−173 (2)	C25—N4—C24—C23	166.44 (17)
O2B—C7—C8—C13	162.6 (15)	C24—N4—C25—C26	−177.46 (17)
N3—C7—C8—C13	−7.9 (3)	C27—N4—C25—C26	59.2 (2)
C13—C8—C9—C10	2.5 (3)	C29—N1—C26—C25	−176.08 (18)
C7—C8—C9—C10	−177.4 (2)	C28—N1—C26—C25	59.8 (2)
C8—C9—C10—C11	−1.2 (3)	N4—C25—C26—N1	−60.9 (2)
C9—C10—C11—C12	−0.3 (3)	C24—N4—C27—C28	178.72 (17)
C10—C11—C12—C13	0.4 (3)	C25—N4—C27—C28	−58.1 (2)
C10—C11—C12—C14	−178.84 (18)	C29—N1—C28—C27	177.58 (17)
C11—C12—C13—C8	1.0 (3)	C26—N1—C28—C27	−58.2 (2)
C14—C12—C13—C8	−179.76 (16)	N4—C27—C28—N1	58.1 (2)
C9—C8—C13—C12	−2.4 (3)	C26—N1—C29—C30	172.24 (18)
C7—C8—C13—C12	177.49 (18)	C28—N1—C29—C30	−65.2 (2)
C15—N2—C14—O1	−2.6 (3)	C1—S2—C32—C31	66.79 (18)
C15—N2—C14—C12	178.37 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···S1	0.83 (2)	2.46 (2)	2.9621 (18)	120 (2)
N3—H3A···S2	0.83 (2)	2.49 (2)	2.9905 (19)	120 (2)
C21—H21B···O2Ai	0.97	2.57	3.43 (3)	148
C21—H21B···O2Bi	0.97	2.34	3.230 (11)	152
C24—H24A···O1ii	0.97	2.54	3.505 (3)	171
C26—H26B···S2ii	0.97	2.85	3.632 (2)	139
C32—H32B···O1iii	0.97	2.49	3.146 (3)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯S1	0.83 (2)	2.46 (2)	2.9621 (18)	120 (2)
N3—H3A⋯S2	0.83 (2)	2.49 (2)	2.9905 (19)	120 (2)
C21—H21B⋯O2A i	0.97	2.57	3.43 (3)	148
C21—H21B⋯O2B i	0.97	2.34	3.230 (11)	152
C24—H24A⋯O1ii	0.97	2.54	3.505 (3)	171
C26—H26B⋯S2ii	0.97	2.85	3.632 (2)	139
C32—H32B⋯O1iii	0.97	2.49	3.146 (3)	125

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