2,4,6-Tris(1-oxo-2-pyridylsulfanylmeth-yl)mesitylene methanol solvate.

In the title compound, C(27)H(27)N(3)O(3)S(3)·CH(4)O, the dihedral angles formed by the mesitylene ring with the three oxopyridyl rings are 89.6 (1), 75.5 (1) and 80.69 (1)°, indicating that all three are nearly perpendicular to the mesitylene ring. Intra-molecular C-H⋯S hydrogen bonds generate S(6) ring motifs. The crystal structure is stabilized by intra-molecular C-H⋯S and inter-molecular C-H⋯O hydrogen bonds and weak C-H⋯π inter-actions.

Related literature

For related literature on the biological activity of N-oxides see: Lobana et al., (1989 ▶); Symons & West (1985 ▶); Katsuyuki et al. (1991 ▶); Bovin et al. (1992 ▶); Leonard et al.(1955 ▶). For related literature on N-oxides, see: Jebas et al. (2005 ▶); Ravindran et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶); Jebas et al. (2005); Ravindran et al. (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C27H27N3O3S3·CH4O

M = 569.74

Monoclinic,

a = 11.9644 (17) Å

b = 14.9129 (8) Å

c = 15.467 (2) Å

β = 91.733 (7)°

V = 2758.4 (6) Å3

Z = 4

Cu Kα radiation

μ = 2.78 mm−1

T = 298 (2) K

0.52 × 0.42 × 0.06 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.296, T max = 0.842

5226 measured reflections

5226 independent reflections

4156 reflections with I > 2σ(I)

3 standard reflections frequency: 60 min intensity decay: 3%

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.150

S = 1.08

5226 reflections

347 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013081/at2565sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013081/at2565Isup2.hkl

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

C27H27N3O3S3·CH4O	F000 = 1200
Mr = 569.74	Dx = 1.372 Mg m−3
Monoclinic, P21/c	Cu Kα radiation λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.9644 (17) Å	θ = 61–69º
b = 14.9129 (8) Å	µ = 2.78 mm−1
c = 15.467 (2) Å	T = 298 (2) K
β = 91.733 (7)º	Block, colourless
V = 2758.4 (6) Å3	0.52 × 0.42 × 0.06 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	θmax = 69.9º
Monochromator: graphite	θmin = 3.7º
ω/2θ scans	h = 0→14
Absorption correction: ψ scan(North et al., 1968)	k = −18→0
Tmin = 0.296, Tmax = 0.842	l = −18→18
5226 measured reflections	3 standard reflections
5226 independent reflections	every 60 min
4156 reflections with I > 2σ(I)	intensity decay: 3%
Rint = 0

Refinement on F2	12 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.051	w = 1/[σ2(Fo2) + (0.0834P)2 + 0.7123P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.150	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.49 e Å−3
5226 reflections	Δρmin = −0.32 e Å−3
347 parameters	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
C1	0.3585 (2)	0.25409 (17)	−0.03619 (16)	0.0411 (6)
C2	0.4031 (2)	0.2831 (2)	−0.11233 (17)	0.0509 (7)
H2	0.4415	0.3372	−0.114	0.061*
C3	0.3906 (3)	0.2318 (2)	−0.18594 (19)	0.0595 (8)
H3	0.4189	0.2516	−0.2379	0.071*
C4	0.3357 (3)	0.1508 (2)	−0.1818 (2)	0.0627 (8)
H4	0.3283	0.1149	−0.2307	0.075*
C5	0.2921 (3)	0.1234 (2)	−0.1054 (2)	0.0593 (8)
H5	0.2552	0.0686	−0.1028	0.071*
N6	0.30179 (19)	0.17480 (15)	−0.03383 (15)	0.0475 (5)
O7	0.2579 (2)	0.15045 (15)	0.03880 (14)	0.0660 (6)
S8	0.36161 (6)	0.30782 (4)	0.06449 (4)	0.04599 (19)
C9	0.4460 (2)	0.40587 (17)	0.04115 (15)	0.0442 (6)
H9A	0.5203	0.3879	0.0245	0.053*
H9B	0.4117	0.4404	−0.0057	0.053*
C10	0.4525 (2)	0.46111 (16)	0.12348 (15)	0.0380 (5)
C11	0.3677 (2)	0.52357 (17)	0.13909 (16)	0.0407 (5)
C12	0.3725 (2)	0.57310 (16)	0.21599 (16)	0.0401 (5)
C13	0.4580 (2)	0.55854 (16)	0.27863 (16)	0.0401 (5)
C14	0.5453 (2)	0.49992 (16)	0.25966 (15)	0.0384 (5)
C15	0.5413 (2)	0.44950 (16)	0.18286 (15)	0.0384 (5)
C16	0.2719 (3)	0.5372 (2)	0.07464 (19)	0.0551 (7)
H16A	0.2881	0.5871	0.0378	0.083*
H16B	0.2047	0.5491	0.1049	0.083*
H16C	0.2621	0.4841	0.0401	0.083*
C17	0.4548 (3)	0.6036 (2)	0.36637 (19)	0.0588 (8)
H17A	0.4966	0.6585	0.3652	0.088*
H17B	0.487	0.5645	0.4096	0.088*
H17C	0.3786	0.6164	0.3799	0.088*
C18	0.6333 (3)	0.3827 (2)	0.16668 (19)	0.0535 (7)
H18A	0.6067	0.3384	0.126	0.08*
H18B	0.6552	0.354	0.2201	0.08*
H18C	0.6964	0.4133	0.1437	0.08*
C19	0.2853 (2)	0.64413 (18)	0.2303 (2)	0.0489 (6)
H19A	0.2688	0.6758	0.1766	0.059*
H19B	0.313	0.6872	0.2728	0.059*
S20	0.15895 (7)	0.59076 (5)	0.26844 (6)	0.0598 (2)
C21	0.0714 (2)	0.6832 (2)	0.2755 (2)	0.0534 (7)
C22	0.0959 (3)	0.7726 (2)	0.2634 (2)	0.0627 (8)
H22	0.167	0.7891	0.2465	0.075*
C23	0.0164 (3)	0.8378 (3)	0.2760 (3)	0.0754 (10)
H23	0.0333	0.898	0.2674	0.09*
C24	−0.0876 (3)	0.8128 (3)	0.3012 (3)	0.0837 (12)
H24	−0.1412	0.8561	0.3121	0.1*
C25	−0.1127 (3)	0.7240 (3)	0.3104 (3)	0.0831 (12)
H25	−0.1841	0.7072	0.3263	0.1*
N26	−0.0351 (2)	0.6605 (2)	0.29666 (19)	0.0687 (8)
O27	−0.0591 (2)	0.57455 (19)	0.3027 (2)	0.0984 (10)
C28	0.6442 (2)	0.49055 (18)	0.32203 (17)	0.0450 (6)
H28A	0.6531	0.5448	0.3561	0.054*
H28B	0.712	0.4813	0.2903	0.054*
S29	0.62016 (6)	0.39480 (5)	0.39312 (5)	0.0517 (2)
C30	0.7555 (2)	0.37491 (19)	0.43343 (17)	0.0475 (6)
C31	0.8492 (3)	0.4281 (2)	0.4247 (2)	0.0604 (8)
H31	0.8431	0.4844	0.3993	0.073*
C32	0.9529 (3)	0.3962 (3)	0.4545 (3)	0.0771 (10)
H32	1.0171	0.4301	0.4475	0.093*
C33	0.9589 (4)	0.3142 (3)	0.4943 (3)	0.0871 (13)
H33	1.0278	0.2922	0.5142	0.104*
C34	0.8648 (4)	0.2647 (3)	0.5050 (2)	0.0772 (11)
H34	0.8701	0.2094	0.5327	0.093*
N35	0.7633 (2)	0.29458 (17)	0.47588 (16)	0.0572 (6)
O36	0.6727 (2)	0.24782 (16)	0.48565 (16)	0.0756 (7)
O1L	−0.1572 (5)	0.5507 (4)	0.1374 (4)	0.205 (2)
H1L	−0.12	0.5136	0.1649	0.308*
C2L	−0.0867 (7)	0.5996 (6)	0.0829 (5)	0.189 (3)
H2LA	−0.0521	0.6478	0.115	0.284*
H2LB	−0.1301	0.6237	0.0351	0.284*
H2LC	−0.03	0.5606	0.0615	0.284*

	U11	U22	U33	U12	U13	U23
C1	0.0480 (14)	0.0322 (12)	0.0432 (13)	0.0010 (10)	0.0013 (11)	−0.0040 (10)
C2	0.0599 (16)	0.0485 (16)	0.0447 (14)	−0.0036 (13)	0.0087 (12)	−0.0060 (12)
C3	0.0659 (19)	0.066 (2)	0.0471 (15)	0.0032 (16)	0.0085 (14)	−0.0108 (14)
C4	0.0639 (18)	0.065 (2)	0.0594 (18)	0.0085 (16)	−0.0044 (15)	−0.0287 (16)
C5	0.0639 (18)	0.0428 (16)	0.071 (2)	−0.0009 (14)	−0.0044 (15)	−0.0194 (14)
N6	0.0517 (12)	0.0371 (12)	0.0536 (13)	−0.0005 (10)	0.0007 (10)	−0.0030 (10)
O7	0.0869 (16)	0.0497 (12)	0.0620 (13)	−0.0199 (11)	0.0136 (12)	0.0040 (10)
S8	0.0649 (4)	0.0383 (3)	0.0351 (3)	−0.0115 (3)	0.0081 (3)	−0.0010 (2)
C9	0.0598 (16)	0.0381 (14)	0.0352 (12)	−0.0108 (12)	0.0078 (11)	−0.0017 (10)
C10	0.0494 (14)	0.0304 (12)	0.0346 (12)	−0.0079 (10)	0.0060 (10)	0.0004 (9)
C11	0.0465 (13)	0.0332 (12)	0.0425 (13)	−0.0049 (10)	0.0034 (11)	0.0048 (10)
C12	0.0450 (13)	0.0290 (12)	0.0467 (13)	−0.0001 (10)	0.0082 (11)	0.0028 (10)
C13	0.0497 (14)	0.0294 (12)	0.0416 (13)	0.0001 (10)	0.0079 (11)	−0.0017 (10)
C14	0.0464 (13)	0.0305 (12)	0.0384 (12)	−0.0026 (10)	0.0037 (10)	0.0024 (10)
C15	0.0477 (13)	0.0293 (12)	0.0387 (12)	−0.0008 (10)	0.0094 (10)	0.0007 (9)
C16	0.0574 (17)	0.0541 (17)	0.0534 (16)	0.0011 (14)	−0.0053 (13)	0.0049 (13)
C17	0.074 (2)	0.0518 (17)	0.0513 (16)	0.0057 (15)	0.0062 (14)	−0.0164 (13)
C18	0.0585 (17)	0.0464 (16)	0.0557 (16)	0.0127 (13)	0.0063 (13)	−0.0059 (13)
C19	0.0485 (14)	0.0331 (13)	0.0655 (17)	0.0037 (11)	0.0095 (13)	0.0016 (12)
S20	0.0567 (4)	0.0417 (4)	0.0823 (5)	0.0054 (3)	0.0209 (4)	0.0093 (3)
C21	0.0492 (15)	0.0523 (17)	0.0592 (17)	0.0065 (13)	0.0094 (13)	0.0061 (13)
C22	0.0565 (17)	0.0502 (17)	0.082 (2)	0.0055 (14)	0.0066 (16)	0.0005 (16)
C23	0.073 (2)	0.054 (2)	0.100 (3)	0.0166 (18)	0.006 (2)	0.0046 (19)
C24	0.074 (2)	0.078 (3)	0.099 (3)	0.032 (2)	0.014 (2)	0.010 (2)
C25	0.0563 (19)	0.096 (3)	0.099 (3)	0.020 (2)	0.0250 (19)	0.020 (2)
N26	0.0583 (15)	0.0674 (18)	0.0815 (19)	0.0050 (14)	0.0231 (14)	0.0188 (15)
O27	0.0813 (18)	0.0709 (17)	0.146 (3)	−0.0036 (14)	0.0488 (18)	0.0273 (17)
C28	0.0495 (14)	0.0383 (14)	0.0471 (14)	−0.0038 (11)	−0.0007 (12)	0.0030 (11)
S29	0.0522 (4)	0.0503 (4)	0.0524 (4)	−0.0049 (3)	−0.0013 (3)	0.0111 (3)
C30	0.0598 (16)	0.0425 (14)	0.0399 (13)	0.0037 (12)	−0.0041 (12)	−0.0029 (11)
C31	0.0605 (18)	0.0562 (18)	0.0639 (18)	−0.0008 (15)	−0.0104 (15)	−0.0032 (15)
C32	0.058 (2)	0.085 (3)	0.087 (3)	0.0017 (18)	−0.0141 (18)	−0.015 (2)
C33	0.080 (3)	0.092 (3)	0.087 (3)	0.030 (2)	−0.032 (2)	−0.016 (2)
C34	0.101 (3)	0.066 (2)	0.064 (2)	0.025 (2)	−0.022 (2)	0.0010 (17)
N35	0.0801 (18)	0.0444 (14)	0.0467 (13)	0.0080 (13)	−0.0035 (12)	0.0002 (11)
O36	0.0988 (18)	0.0528 (14)	0.0755 (15)	−0.0065 (13)	0.0083 (14)	0.0178 (12)
O1L	0.213 (4)	0.187 (4)	0.214 (4)	−0.065 (4)	−0.012 (3)	−0.012 (3)
C2L	0.178 (5)	0.210 (5)	0.179 (5)	−0.041 (4)	−0.017 (4)	0.006 (4)

C1—N6	1.364 (3)	C19—S20	1.822 (3)
C1—C2	1.377 (4)	C19—H19A	0.97
C1—S8	1.751 (2)	C19—H19B	0.97
C2—C3	1.376 (4)	S20—C21	1.737 (3)
C2—H2	0.93	C21—N26	1.368 (4)
C3—C4	1.377 (5)	C21—C22	1.378 (4)
C3—H3	0.93	C22—C23	1.379 (4)
C4—C5	1.368 (5)	C22—H22	0.93
C4—H4	0.93	C23—C24	1.368 (5)
C5—N6	1.349 (4)	C23—H23	0.93
C5—H5	0.93	C24—C25	1.366 (6)
N6—O7	1.306 (3)	C24—H24	0.93
S8—C9	1.820 (3)	C25—N26	1.348 (5)
C9—C10	1.517 (3)	C25—H25	0.93
C9—H9A	0.97	N26—O27	1.318 (4)
C9—H9B	0.97	C28—S29	1.830 (3)
C10—C15	1.394 (4)	C28—H28A	0.97
C10—C11	1.404 (4)	C28—H28B	0.97
C11—C12	1.400 (4)	S29—C30	1.742 (3)
C11—C16	1.510 (4)	C30—N35	1.368 (4)
C12—C13	1.404 (4)	C30—C31	1.384 (4)
C12—C19	1.508 (3)	C31—C32	1.394 (5)
C13—C14	1.400 (3)	C31—H31	0.93
C13—C17	1.516 (4)	C32—C33	1.370 (6)
C14—C15	1.406 (3)	C32—H32	0.93
C14—C28	1.510 (3)	C33—C34	1.361 (6)
C15—C18	1.511 (4)	C33—H33	0.93
C16—H16A	0.96	C34—N35	1.358 (4)
C16—H16B	0.96	C34—H34	0.93
C16—H16C	0.96	N35—O36	1.302 (4)
C17—H17A	0.96	O1L—C2L	1.414 (9)
C17—H17B	0.96	O1L—H1L	0.82
C17—H17C	0.96	C2L—H2LA	0.96
C18—H18A	0.96	C2L—H2LB	0.96
C18—H18B	0.96	C2L—H2LC	0.96
C18—H18C	0.96
N6—C1—C2	120.1 (2)	H18A—C18—H18C	109.5
N6—C1—S8	111.72 (18)	H18B—C18—H18C	109.5
C2—C1—S8	128.2 (2)	C12—C19—S20	108.98 (18)
C3—C2—C1	119.8 (3)	C12—C19—H19A	109.9
C3—C2—H2	120.1	S20—C19—H19A	109.9
C1—C2—H2	120.1	C12—C19—H19B	109.9
C2—C3—C4	119.3 (3)	S20—C19—H19B	109.9
C2—C3—H3	120.4	H19A—C19—H19B	108.3
C4—C3—H3	120.4	C21—S20—C19	100.44 (13)
C5—C4—C3	119.8 (3)	N26—C21—C22	118.4 (3)
C5—C4—H4	120.1	N26—C21—S20	112.7 (2)
C3—C4—H4	120.1	C22—C21—S20	128.9 (2)
N6—C5—C4	120.9 (3)	C21—C22—C23	120.8 (3)
N6—C5—H5	119.6	C21—C22—H22	119.6
C4—C5—H5	119.6	C23—C22—H22	119.6
O7—N6—C5	121.4 (2)	C24—C23—C22	119.0 (4)
O7—N6—C1	118.5 (2)	C24—C23—H23	120.5
C5—N6—C1	120.1 (3)	C22—C23—H23	120.5
C1—S8—C9	100.86 (12)	C25—C24—C23	119.9 (3)
C10—C9—S8	106.53 (16)	C25—C24—H24	120
C10—C9—H9A	110.4	C23—C24—H24	120
S8—C9—H9A	110.4	N26—C25—C24	120.7 (3)
C10—C9—H9B	110.4	N26—C25—H25	119.7
S8—C9—H9B	110.4	C24—C25—H25	119.7
H9A—C9—H9B	108.6	O27—N26—C25	121.3 (3)
C15—C10—C11	120.6 (2)	O27—N26—C21	117.7 (3)
C15—C10—C9	120.3 (2)	C25—N26—C21	121.0 (3)
C11—C10—C9	119.1 (2)	C14—C28—S29	108.76 (17)
C12—C11—C10	119.0 (2)	C14—C28—H28A	109.9
C12—C11—C16	120.1 (2)	S29—C28—H28A	109.9
C10—C11—C16	120.9 (2)	C14—C28—H28B	109.9
C11—C12—C13	121.0 (2)	S29—C28—H28B	109.9
C11—C12—C19	119.0 (2)	H28A—C28—H28B	108.3
C13—C12—C19	120.0 (2)	C30—S29—C28	100.76 (13)
C14—C13—C12	119.0 (2)	N35—C30—C31	120.3 (3)
C14—C13—C17	120.3 (2)	N35—C30—S29	111.7 (2)
C12—C13—C17	120.7 (2)	C31—C30—S29	127.9 (2)
C13—C14—C15	120.3 (2)	C30—C31—C32	119.2 (3)
C13—C14—C28	119.9 (2)	C30—C31—H31	120.4
C15—C14—C28	119.8 (2)	C32—C31—H31	120.4
C10—C15—C14	119.8 (2)	C33—C32—C31	119.2 (4)
C10—C15—C18	121.1 (2)	C33—C32—H32	120.4
C14—C15—C18	119.1 (2)	C31—C32—H32	120.4
C11—C16—H16A	109.5	C34—C33—C32	120.4 (4)
C11—C16—H16B	109.5	C34—C33—H33	119.8
H16A—C16—H16B	109.5	C32—C33—H33	119.8
C11—C16—H16C	109.5	N35—C34—C33	121.1 (4)
H16A—C16—H16C	109.5	N35—C34—H34	119.4
H16B—C16—H16C	109.5	C33—C34—H34	119.4
C13—C17—H17A	109.5	O36—N35—C34	121.7 (3)
C13—C17—H17B	109.5	O36—N35—C30	118.7 (3)
H17A—C17—H17B	109.5	C34—N35—C30	119.6 (3)
C13—C17—H17C	109.5	C2L—O1L—H1L	109.5
H17A—C17—H17C	109.5	O1L—C2L—H2LA	109.5
H17B—C17—H17C	109.5	O1L—C2L—H2LB	109.5
C15—C18—H18A	109.5	H2LA—C2L—H2LB	109.5
C15—C18—H18B	109.5	O1L—C2L—H2LC	109.5
H18A—C18—H18B	109.5	H2LA—C2L—H2LC	109.5
C15—C18—H18C	109.5	H2LB—C2L—H2LC	109.5
N6—C1—C2—C3	−0.2 (4)	C13—C14—C15—C10	3.0 (3)
S8—C1—C2—C3	−178.9 (2)	C28—C14—C15—C10	−177.1 (2)
C1—C2—C3—C4	−1.6 (5)	C13—C14—C15—C18	−176.4 (2)
C2—C3—C4—C5	1.6 (5)	C28—C14—C15—C18	3.5 (3)
C3—C4—C5—N6	0.2 (5)	C11—C12—C19—S20	81.2 (3)
C4—C5—N6—O7	178.1 (3)	C13—C12—C19—S20	−99.9 (2)
C4—C5—N6—C1	−1.9 (4)	C12—C19—S20—C21	−177.6 (2)
C2—C1—N6—O7	−178.1 (3)	C19—S20—C21—N26	174.9 (2)
S8—C1—N6—O7	0.8 (3)	C19—S20—C21—C22	−5.5 (4)
C2—C1—N6—C5	1.9 (4)	N26—C21—C22—C23	2.8 (5)
S8—C1—N6—C5	−179.1 (2)	S20—C21—C22—C23	−176.7 (3)
N6—C1—S8—C9	177.65 (19)	C21—C22—C23—C24	0.3 (6)
C2—C1—S8—C9	−3.5 (3)	C22—C23—C24—C25	−2.5 (7)
C1—S8—C9—C10	178.14 (19)	C23—C24—C25—N26	1.5 (7)
S8—C9—C10—C15	92.9 (2)	C24—C25—N26—O27	−177.9 (4)
S8—C9—C10—C11	−86.7 (2)	C24—C25—N26—C21	1.8 (6)
C15—C10—C11—C12	−1.1 (3)	C22—C21—N26—O27	175.8 (3)
C9—C10—C11—C12	178.6 (2)	S20—C21—N26—O27	−4.5 (4)
C15—C10—C11—C16	179.3 (2)	C22—C21—N26—C25	−3.9 (5)
C9—C10—C11—C16	−1.0 (3)	S20—C21—N26—C25	175.7 (3)
C10—C11—C12—C13	−2.6 (4)	C13—C14—C28—S29	94.8 (2)
C16—C11—C12—C13	177.0 (2)	C15—C14—C28—S29	−85.0 (2)
C10—C11—C12—C19	176.3 (2)	C14—C28—S29—C30	162.19 (18)
C16—C11—C12—C19	−4.1 (4)	C28—S29—C30—N35	−168.0 (2)
C11—C12—C13—C14	6.3 (4)	C28—S29—C30—C31	10.1 (3)
C19—C12—C13—C14	−172.5 (2)	N35—C30—C31—C32	4.3 (5)
C11—C12—C13—C17	−172.2 (2)	S29—C30—C31—C32	−173.7 (3)
C19—C12—C13—C17	9.0 (4)	C30—C31—C32—C33	−2.1 (5)
C12—C13—C14—C15	−6.5 (3)	C31—C32—C33—C34	−0.3 (6)
C17—C13—C14—C15	172.0 (2)	C32—C33—C34—N35	0.7 (6)
C12—C13—C14—C28	173.6 (2)	C33—C34—N35—O36	180.0 (3)
C17—C13—C14—C28	−7.9 (4)	C33—C34—N35—C30	1.4 (5)
C11—C10—C15—C14	0.8 (3)	C31—C30—N35—O36	177.5 (3)
C9—C10—C15—C14	−178.9 (2)	S29—C30—N35—O36	−4.2 (3)
C11—C10—C15—C18	−179.8 (2)	C31—C30—N35—C34	−3.9 (4)
C9—C10—C15—C18	0.5 (3)	S29—C30—N35—C34	174.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1L—H1L···O27	0.82	2.41	2.804 (7)	110
C16—H16A···O36i	0.96	2.47	3.348 (4)	152
C16—H16B···S20	0.96	2.68	3.420 (3)	135
C18—H18B···S29	0.96	2.79	3.515 (3)	133
C25—H25···O7ii	0.93	2.44	3.147 (5)	133
C28—H28A···O7i	0.97	2.48	3.397 (3)	157
C31—H31···O27iii	0.93	2.35	3.107 (4)	139
C2—H2···Cg1iv	0.93	2.91	3.774 (3)	154
C4—H4···Cg1v	0.93	2.67	3.377 (3)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1L—H1L⋯O27	0.82	2.41	2.804 (7)	110
C16—H16A⋯O36i	0.96	2.47	3.348 (4)	152
C16—H16B⋯S20	0.96	2.68	3.420 (3)	135
C18—H18B⋯S29	0.96	2.79	3.515 (3)	133
C25—H25⋯O7ii	0.93	2.44	3.147 (5)	133
C28—H28A⋯O7i	0.97	2.48	3.397 (3)	157
C31—H31⋯O27iii	0.93	2.35	3.107 (4)	139
C2—H2⋯Cg1iv	0.93	2.91	3.774 (3)	154
C4—H4⋯Cg1v	0.93	2.67	3.377 (3)	134

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg1 is the centroid of the C10–C15 ring.