3-(Adamantan-1-yl)-1-[(4-ethyl-piperazin-1-yl)meth-yl]-4-[(E)-(4-hy-droxy-benzyl-idene)amino]-1H-1,2,4-triazole-5(4H)-thione.

In the title thione, C(26)H(36)N(6)OS, the 1,2,4-triazole ring is planar (r.m.s. deviation = 0.020 Å) and the benzene ring is twisted out of this plane [dihedral angle = 62.35 (12)°]. Supra-molecular zigzag chains feature in the crystal packing. These are sustained by O-H⋯N(piperazine) hydrogen bonds, and are connected into the three-dimensional crystal structure by C-H⋯S and C-H⋯O inter-actions. The crystal studied was a racemic twin.

Related literature

For the biological activity of adamantyl derivatives, see: Vernier et al. (1969 ▶); El-Emam et al. (2004 ▶); Kadi et al. (2007 ▶, 2010 ▶); Al-Omar et al. (2010 ▶). For related adamantane structures, see: Al-Tamimi et al. (2010 ▶); Kadi et al. (2011 ▶).

Experimental

Crystal data

C26H36N6OS

M = 480.67

Monoclinic,

a = 16.1006 (6) Å

b = 14.2182 (5) Å

c = 11.4641 (4) Å

β = 92.440 (4)°

V = 2622.00 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.15 mm−1

T = 100 K

0.25 × 0.20 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.963, T max = 0.977

12526 measured reflections

4840 independent reflections

4374 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.100

S = 1.03

4840 reflections

312 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), with 1811 Friedel pairs

Flack parameter: 0.06 (7)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005107/hg5175sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005107/hg5175Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005107/hg5175Isup3.cml

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

C26H36N6OS	F(000) = 1032
Mr = 480.67	Dx = 1.218 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 4991 reflections
a = 16.1006 (6) Å	θ = 2.5–27.5°
b = 14.2182 (5) Å	µ = 0.15 mm−1
c = 11.4641 (4) Å	T = 100 K
β = 92.440 (4)°	Prism, colourless
V = 2622.00 (16) Å3	0.25 × 0.20 × 0.15 mm
Z = 4

Agilent SuperNova Dual diffractometer with Atlas detector	4840 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4374 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.036
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.5°
ω scans	h = −20→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −18→18
Tmin = 0.963, Tmax = 0.977	l = −14→14
12526 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0544P)2 + 0.5109P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
4840 reflections	Δρmax = 0.25 e Å−3
312 parameters	Δρmin = −0.18 e Å−3
3 restraints	Absolute structure: Flack (1983), with 1811 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.06 (7)

	x	y	z	Uiso*/Ueq
S1	0.49872 (4)	0.56121 (4)	0.50028 (4)	0.02603 (13)
O1	0.57958 (13)	1.01838 (13)	0.12630 (14)	0.0397 (5)
H1O	0.602 (3)	1.0657 (19)	0.160 (4)	0.103 (16)*
N1	0.38211 (12)	0.55968 (12)	0.66504 (16)	0.0249 (4)
N2	0.32689 (12)	0.61698 (13)	0.71956 (16)	0.0268 (4)
N3	0.38731 (11)	0.69230 (12)	0.57892 (15)	0.0201 (4)
N4	0.41828 (11)	0.77076 (12)	0.51938 (14)	0.0210 (4)
N5	0.32453 (12)	0.40404 (13)	0.71060 (16)	0.0257 (4)
N6	0.16089 (12)	0.32789 (13)	0.70910 (17)	0.0292 (4)
C1	0.28270 (14)	0.78354 (15)	0.69923 (18)	0.0244 (5)
C2	0.34125 (17)	0.85912 (18)	0.7529 (2)	0.0387 (6)
H2A	0.3724	0.8331	0.8219	0.046*
H2B	0.3818	0.8788	0.6952	0.046*
C3	0.2896 (2)	0.9442 (2)	0.7892 (3)	0.0545 (9)
H3	0.3275	0.9931	0.8245	0.065*
C4	0.2445 (2)	0.98457 (18)	0.6805 (3)	0.0486 (8)
H4A	0.2134	1.0418	0.7014	0.058*
H4B	0.2853	1.0021	0.6221	0.058*
C5	0.18436 (17)	0.91073 (17)	0.6291 (2)	0.0350 (6)
H5	0.1535	0.9376	0.5593	0.042*
C6	0.12260 (17)	0.88242 (19)	0.7202 (2)	0.0409 (6)
H6A	0.0906	0.9382	0.7439	0.049*
H6B	0.0829	0.8356	0.6864	0.049*
C7	0.1689 (2)	0.8407 (2)	0.8263 (2)	0.0474 (8)
H7	0.1281	0.8216	0.8853	0.057*
C8	0.2276 (2)	0.9136 (3)	0.8790 (3)	0.0678 (12)
H8A	0.2579	0.8870	0.9483	0.081*
H8B	0.1956	0.9688	0.9045	0.081*
C9	0.21912 (18)	0.75416 (19)	0.7898 (2)	0.0408 (7)
H9A	0.1810	0.7059	0.7556	0.049*
H9B	0.2486	0.7266	0.8592	0.049*
C10	0.23419 (15)	0.82507 (16)	0.5923 (2)	0.0281 (5)
H10A	0.2735	0.8437	0.5323	0.034*
H10B	0.1961	0.7770	0.5578	0.034*
C11	0.33174 (14)	0.69771 (15)	0.66707 (18)	0.0231 (4)
C12	0.42254 (13)	0.60297 (14)	0.58011 (18)	0.0205 (4)
C13	0.39656 (14)	0.46264 (15)	0.7065 (2)	0.0273 (5)
H13A	0.4365	0.4323	0.6551	0.033*
H13B	0.4232	0.4655	0.7859	0.033*
C14	0.27018 (14)	0.42163 (15)	0.80734 (18)	0.0240 (5)
H14A	0.2378	0.4799	0.7926	0.029*
H14B	0.3039	0.4297	0.8809	0.029*
C15	0.21187 (14)	0.33867 (16)	0.8179 (2)	0.0278 (5)
H15A	0.2445	0.2806	0.8333	0.033*
H15B	0.1754	0.3489	0.8841	0.033*
C16	0.21480 (17)	0.31573 (17)	0.6094 (2)	0.0353 (6)
H16A	0.1800	0.3122	0.5363	0.042*
H16B	0.2457	0.2558	0.6184	0.042*
C17	0.27601 (17)	0.39628 (17)	0.6011 (2)	0.0323 (5)
H17A	0.3134	0.3847	0.5362	0.039*
H17B	0.2456	0.4557	0.5850	0.039*
C18	0.10554 (18)	0.24398 (19)	0.7131 (3)	0.0436 (7)
H18A	0.1404	0.1868	0.7211	0.052*
H18B	0.0729	0.2393	0.6381	0.052*
C19	0.04676 (18)	0.2464 (2)	0.8111 (3)	0.0496 (7)
H19A	0.0136	0.1886	0.8101	0.074*
H19B	0.0098	0.3009	0.8014	0.074*
H19C	0.0785	0.2514	0.8857	0.074*
C20	0.42424 (13)	0.75687 (15)	0.40960 (18)	0.0211 (4)
H20	0.4039	0.7001	0.3753	0.025*
C21	0.46203 (13)	0.82785 (14)	0.33739 (18)	0.0213 (4)
C22	0.50449 (14)	0.90456 (15)	0.38680 (19)	0.0250 (5)
H22	0.5069	0.9122	0.4692	0.030*
C23	0.54296 (15)	0.96938 (15)	0.31823 (19)	0.0267 (5)
H23	0.5711	1.0216	0.3534	0.032*
C24	0.54077 (15)	0.95855 (17)	0.19726 (19)	0.0284 (5)
C25	0.49716 (16)	0.88341 (18)	0.1466 (2)	0.0325 (6)
H25	0.4938	0.8768	0.0640	0.039*
C26	0.45868 (15)	0.81838 (16)	0.21584 (18)	0.0275 (5)
H26	0.4297	0.7668	0.1806	0.033*

	U11	U22	U33	U12	U13	U23
S1	0.0246 (3)	0.0275 (2)	0.0267 (3)	0.0066 (2)	0.0095 (2)	0.0022 (2)
O1	0.0465 (12)	0.0445 (10)	0.0276 (9)	−0.0220 (9)	−0.0034 (8)	0.0134 (8)
N1	0.0260 (10)	0.0223 (9)	0.0272 (9)	0.0052 (8)	0.0092 (8)	0.0052 (7)
N2	0.0282 (10)	0.0265 (9)	0.0266 (9)	0.0083 (8)	0.0129 (8)	0.0063 (8)
N3	0.0206 (9)	0.0206 (8)	0.0196 (8)	0.0011 (7)	0.0060 (7)	0.0006 (7)
N4	0.0205 (9)	0.0217 (8)	0.0212 (9)	−0.0005 (7)	0.0042 (7)	0.0046 (7)
N5	0.0257 (10)	0.0230 (9)	0.0288 (9)	0.0039 (8)	0.0056 (8)	0.0029 (8)
N6	0.0253 (11)	0.0304 (10)	0.0319 (10)	0.0012 (8)	0.0030 (8)	−0.0066 (8)
C1	0.0272 (12)	0.0259 (11)	0.0206 (10)	0.0077 (9)	0.0068 (9)	0.0033 (9)
C2	0.0395 (15)	0.0363 (13)	0.0396 (14)	0.0138 (12)	−0.0057 (12)	−0.0131 (12)
C3	0.0535 (19)	0.0411 (16)	0.068 (2)	0.0176 (14)	−0.0071 (17)	−0.0274 (15)
C4	0.0480 (18)	0.0238 (12)	0.075 (2)	0.0142 (12)	0.0164 (15)	0.0012 (13)
C5	0.0321 (14)	0.0366 (12)	0.0369 (14)	0.0157 (11)	0.0105 (11)	0.0127 (11)
C6	0.0364 (15)	0.0418 (14)	0.0459 (15)	0.0190 (12)	0.0185 (12)	0.0127 (12)
C7	0.0552 (19)	0.0547 (17)	0.0344 (14)	0.0306 (15)	0.0245 (13)	0.0088 (13)
C8	0.083 (3)	0.082 (2)	0.0383 (16)	0.057 (2)	0.0067 (17)	−0.0153 (16)
C9	0.0424 (16)	0.0485 (15)	0.0334 (13)	0.0243 (13)	0.0248 (12)	0.0166 (12)
C10	0.0256 (12)	0.0369 (12)	0.0223 (10)	0.0081 (10)	0.0054 (9)	0.0047 (10)
C11	0.0249 (11)	0.0261 (10)	0.0186 (10)	0.0036 (9)	0.0059 (8)	0.0043 (9)
C12	0.0196 (11)	0.0219 (10)	0.0200 (10)	0.0016 (8)	0.0005 (8)	−0.0004 (9)
C13	0.0249 (12)	0.0245 (10)	0.0332 (12)	0.0062 (9)	0.0083 (10)	0.0106 (10)
C14	0.0236 (12)	0.0257 (10)	0.0226 (10)	0.0018 (9)	0.0012 (9)	0.0021 (9)
C15	0.0223 (12)	0.0295 (11)	0.0318 (12)	0.0020 (9)	0.0035 (10)	0.0037 (10)
C16	0.0367 (15)	0.0345 (12)	0.0348 (13)	0.0057 (11)	0.0028 (11)	−0.0121 (11)
C17	0.0391 (15)	0.0321 (12)	0.0261 (11)	0.0082 (10)	0.0043 (10)	−0.0020 (10)
C18	0.0300 (15)	0.0367 (13)	0.0640 (18)	−0.0040 (11)	0.0005 (13)	−0.0110 (13)
C19	0.0297 (15)	0.0518 (16)	0.067 (2)	−0.0095 (13)	0.0024 (14)	−0.0083 (15)
C20	0.0181 (11)	0.0201 (9)	0.0252 (11)	0.0008 (8)	0.0032 (8)	0.0020 (8)
C21	0.0189 (11)	0.0234 (10)	0.0217 (10)	0.0012 (8)	0.0027 (8)	0.0042 (9)
C22	0.0260 (12)	0.0276 (10)	0.0216 (10)	−0.0014 (9)	0.0018 (9)	0.0015 (9)
C23	0.0282 (12)	0.0243 (10)	0.0274 (11)	−0.0080 (9)	0.0001 (10)	0.0027 (9)
C24	0.0262 (12)	0.0323 (12)	0.0265 (11)	−0.0065 (9)	−0.0002 (10)	0.0103 (9)
C25	0.0362 (15)	0.0405 (13)	0.0206 (10)	−0.0119 (11)	−0.0007 (10)	0.0054 (10)
C26	0.0286 (13)	0.0293 (11)	0.0246 (11)	−0.0078 (10)	0.0020 (10)	0.0002 (9)

S1—C12	1.670 (2)	C7—H7	1.0000
O1—C24	1.349 (3)	C8—H8A	0.9900
O1—H1O	0.850 (10)	C8—H8B	0.9900
N1—C12	1.343 (3)	C9—H9A	0.9900
N1—N2	1.376 (3)	C9—H9B	0.9900
N1—C13	1.475 (3)	C10—H10A	0.9900
N2—C11	1.300 (3)	C10—H10B	0.9900
N3—C11	1.380 (3)	C13—H13A	0.9900
N3—C12	1.391 (3)	C13—H13B	0.9900
N3—N4	1.410 (2)	C14—C15	1.516 (3)
N4—C20	1.282 (3)	C14—H14A	0.9900
N5—C13	1.430 (3)	C14—H14B	0.9900
N5—C17	1.455 (3)	C15—H15A	0.9900
N5—C14	1.463 (3)	C15—H15B	0.9900
N6—C15	1.472 (3)	C16—C17	1.517 (4)
N6—C16	1.474 (3)	C16—H16A	0.9900
N6—C18	1.491 (3)	C16—H16B	0.9900
C1—C11	1.508 (3)	C17—H17A	0.9900
C1—C10	1.543 (3)	C17—H17B	0.9900
C1—C2	1.540 (3)	C18—C19	1.500 (4)
C1—C9	1.547 (3)	C18—H18A	0.9900
C2—C3	1.535 (3)	C18—H18B	0.9900
C2—H2A	0.9900	C19—H19A	0.9800
C2—H2B	0.9900	C19—H19B	0.9800
C3—C8	1.527 (6)	C19—H19C	0.9800
C3—C4	1.527 (4)	C20—C21	1.455 (3)
C3—H3	1.0000	C20—H20	0.9500
C4—C5	1.529 (4)	C21—C22	1.395 (3)
C4—H4A	0.9900	C21—C26	1.399 (3)
C4—H4B	0.9900	C22—C23	1.376 (3)
C5—C6	1.527 (4)	C22—H22	0.9500
C5—C10	1.528 (3)	C23—C24	1.394 (3)
C5—H5	1.0000	C23—H23	0.9500
C6—C7	1.519 (4)	C24—C25	1.392 (3)
C6—H6A	0.9900	C25—C26	1.382 (3)
C6—H6B	0.9900	C25—H25	0.9500
C7—C8	1.512 (5)	C26—H26	0.9500
C7—C9	1.540 (3)
C24—O1—H1O	115 (3)	C5—C10—H10B	109.7
C12—N1—N2	113.61 (17)	C1—C10—H10B	109.7
C12—N1—C13	126.00 (18)	H10A—C10—H10B	108.2
N2—N1—C13	120.25 (18)	N2—C11—N3	110.08 (19)
C11—N2—N1	105.06 (18)	N2—C11—C1	124.0 (2)
C11—N3—C12	108.69 (17)	N3—C11—C1	125.92 (19)
C11—N3—N4	124.34 (18)	N1—C12—N3	102.45 (18)
C12—N3—N4	125.08 (18)	N1—C12—S1	128.61 (15)
C20—N4—N3	113.35 (17)	N3—C12—S1	128.90 (16)
C13—N5—C17	114.98 (19)	N5—C13—N1	116.01 (18)
C13—N5—C14	115.93 (18)	N5—C13—H13A	108.3
C17—N5—C14	110.53 (18)	N1—C13—H13A	108.3
C15—N6—C16	110.09 (18)	N5—C13—H13B	108.3
C15—N6—C18	111.71 (19)	N1—C13—H13B	108.3
C16—N6—C18	107.59 (19)	H13A—C13—H13B	107.4
C11—C1—C10	111.59 (18)	N5—C14—C15	108.67 (18)
C11—C1—C2	110.14 (19)	N5—C14—H14A	110.0
C10—C1—C2	109.34 (19)	C15—C14—H14A	110.0
C11—C1—C9	108.30 (18)	N5—C14—H14B	110.0
C10—C1—C9	108.06 (19)	C15—C14—H14B	110.0
C2—C1—C9	109.3 (2)	H14A—C14—H14B	108.3
C3—C2—C1	109.2 (2)	N6—C15—C14	109.78 (18)
C3—C2—H2A	109.8	N6—C15—H15A	109.7
C1—C2—H2A	109.8	C14—C15—H15A	109.7
C3—C2—H2B	109.8	N6—C15—H15B	109.7
C1—C2—H2B	109.8	C14—C15—H15B	109.7
H2A—C2—H2B	108.3	H15A—C15—H15B	108.2
C8—C3—C4	110.8 (3)	N6—C16—C17	111.47 (19)
C8—C3—C2	109.6 (3)	N6—C16—H16A	109.3
C4—C3—C2	108.6 (2)	C17—C16—H16A	109.3
C8—C3—H3	109.3	N6—C16—H16B	109.3
C4—C3—H3	109.3	C17—C16—H16B	109.3
C2—C3—H3	109.3	H16A—C16—H16B	108.0
C5—C4—C3	109.1 (2)	N5—C17—C16	109.2 (2)
C5—C4—H4A	109.9	N5—C17—H17A	109.8
C3—C4—H4A	109.9	C16—C17—H17A	109.8
C5—C4—H4B	109.9	N5—C17—H17B	109.8
C3—C4—H4B	109.9	C16—C17—H17B	109.8
H4A—C4—H4B	108.3	H17A—C17—H17B	108.3
C6—C5—C10	110.1 (2)	N6—C18—C19	113.7 (2)
C6—C5—C4	109.7 (2)	N6—C18—H18A	108.8
C10—C5—C4	108.8 (2)	C19—C18—H18A	108.8
C6—C5—H5	109.4	N6—C18—H18B	108.8
C10—C5—H5	109.4	C19—C18—H18B	108.8
C4—C5—H5	109.4	H18A—C18—H18B	107.7
C7—C6—C5	109.8 (2)	C18—C19—H19A	109.5
C7—C6—H6A	109.7	C18—C19—H19B	109.5
C5—C6—H6A	109.7	H19A—C19—H19B	109.5
C7—C6—H6B	109.7	C18—C19—H19C	109.5
C5—C6—H6B	109.7	H19A—C19—H19C	109.5
H6A—C6—H6B	108.2	H19B—C19—H19C	109.5
C8—C7—C6	109.2 (3)	N4—C20—C21	120.16 (19)
C8—C7—C9	109.3 (3)	N4—C20—H20	119.9
C6—C7—C9	109.9 (2)	C21—C20—H20	119.9
C8—C7—H7	109.5	C22—C21—C26	118.51 (19)
C6—C7—H7	109.5	C22—C21—C20	121.40 (19)
C9—C7—H7	109.5	C26—C21—C20	120.05 (19)
C7—C8—C3	109.9 (2)	C23—C22—C21	121.1 (2)
C7—C8—H8A	109.7	C23—C22—H22	119.4
C3—C8—H8A	109.7	C21—C22—H22	119.4
C7—C8—H8B	109.7	C22—C23—C24	120.1 (2)
C3—C8—H8B	109.7	C22—C23—H23	120.0
H8A—C8—H8B	108.2	C24—C23—H23	120.0
C7—C9—C1	109.7 (2)	O1—C24—C25	118.1 (2)
C7—C9—H9A	109.7	O1—C24—C23	122.5 (2)
C1—C9—H9A	109.7	C25—C24—C23	119.4 (2)
C7—C9—H9B	109.7	C26—C25—C24	120.3 (2)
C1—C9—H9B	109.7	C26—C25—H25	119.9
H9A—C9—H9B	108.2	C24—C25—H25	119.9
C5—C10—C1	109.84 (19)	C25—C26—C21	120.6 (2)
C5—C10—H10A	109.7	C25—C26—H26	119.7
C1—C10—H10A	109.7	C21—C26—H26	119.7
C12—N1—N2—C11	0.8 (2)	C10—C1—C11—N3	52.9 (3)
C13—N1—N2—C11	176.73 (19)	C2—C1—C11—N3	−68.8 (3)
C11—N3—N4—C20	−140.2 (2)	C9—C1—C11—N3	171.7 (2)
C12—N3—N4—C20	57.3 (3)	N2—N1—C12—N3	−2.5 (2)
C11—C1—C2—C3	−177.9 (2)	C13—N1—C12—N3	−178.14 (19)
C10—C1—C2—C3	59.2 (3)	N2—N1—C12—S1	175.18 (16)
C9—C1—C2—C3	−59.0 (3)	C13—N1—C12—S1	−0.5 (3)
C1—C2—C3—C8	60.0 (3)	C11—N3—C12—N1	3.2 (2)
C1—C2—C3—C4	−61.2 (3)	N4—N3—C12—N1	168.07 (18)
C8—C3—C4—C5	−57.6 (3)	C11—N3—C12—S1	−174.48 (16)
C2—C3—C4—C5	62.8 (3)	N4—N3—C12—S1	−9.6 (3)
C3—C4—C5—C6	58.3 (3)	C17—N5—C13—N1	55.3 (3)
C3—C4—C5—C10	−62.2 (3)	C14—N5—C13—N1	−75.8 (2)
C10—C5—C6—C7	59.2 (3)	C12—N1—C13—N5	−128.4 (2)
C4—C5—C6—C7	−60.5 (3)	N2—N1—C13—N5	56.2 (3)
C5—C6—C7—C8	60.8 (3)	C13—N5—C14—C15	−164.70 (17)
C5—C6—C7—C9	−59.0 (3)	C17—N5—C14—C15	62.2 (2)
C6—C7—C8—C3	−59.5 (3)	C16—N6—C15—C14	57.6 (2)
C9—C7—C8—C3	60.8 (3)	C18—N6—C15—C14	177.0 (2)
C4—C3—C8—C7	58.6 (3)	N5—C14—C15—N6	−60.5 (2)
C2—C3—C8—C7	−61.2 (3)	C15—N6—C16—C17	−55.8 (2)
C8—C7—C9—C1	−59.7 (3)	C18—N6—C16—C17	−177.7 (2)
C6—C7—C9—C1	60.1 (3)	C13—N5—C17—C16	166.65 (19)
C11—C1—C9—C7	179.0 (2)	C14—N5—C17—C16	−59.7 (2)
C10—C1—C9—C7	−59.9 (3)	N6—C16—C17—N5	56.4 (2)
C2—C1—C9—C7	59.0 (3)	C15—N6—C18—C19	59.0 (3)
C6—C5—C10—C1	−60.2 (3)	C16—N6—C18—C19	179.9 (2)
C4—C5—C10—C1	60.1 (3)	N3—N4—C20—C21	−174.54 (17)
C11—C1—C10—C5	179.1 (2)	N4—C20—C21—C22	10.6 (3)
C2—C1—C10—C5	−58.8 (3)	N4—C20—C21—C26	−171.5 (2)
C9—C1—C10—C5	60.1 (3)	C26—C21—C22—C23	−0.5 (3)
N1—N2—C11—N3	1.3 (2)	C20—C21—C22—C23	177.3 (2)
N1—N2—C11—C1	−179.0 (2)	C21—C22—C23—C24	−0.7 (4)
C12—N3—C11—N2	−3.0 (2)	C22—C23—C24—O1	−177.9 (2)
N4—N3—C11—N2	−167.98 (19)	C22—C23—C24—C25	2.0 (4)
C12—N3—C11—C1	177.3 (2)	O1—C24—C25—C26	177.8 (2)
N4—N3—C11—C1	12.3 (3)	C23—C24—C25—C26	−2.1 (4)
C10—C1—C11—N2	−126.8 (2)	C24—C25—C26—C21	0.9 (4)
C2—C1—C11—N2	111.6 (3)	C22—C21—C26—C25	0.4 (3)
C9—C1—C11—N2	−8.0 (3)	C20—C21—C26—C25	−177.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N6i	0.85 (1)	1.86 (1)	2.699 (3)	170 (5)
C13—H13B···S1ii	0.99	2.72	3.700 (2)	170
C22—H22···O1iii	0.95	2.33	3.149 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N6i	0.85 (1)	1.86 (1)	2.699 (3)	170 (5)
C13—H13B⋯S1ii	0.99	2.72	3.700 (2)	170
C22—H22⋯O1iii	0.95	2.33	3.149 (3)	145

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