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

In the title compound, C(31)H(38)N(6)OS, the conformation about the N=C [1.285 (2) Å] imine bond is E. The piperazine ring has a chair conformation and occupies a position almost perpendicular to the plane through the triazole ring; the benzene ring forms a dihedral angle of 31.95 (10)° with the triazole ring. Overall, the mol-ecule has the shape of a flattened bowl. The hy-droxy group is disordered over two positions. The major component has a site-occupancy factor of 0.762 (3) and forms an intra-molecular O-H⋯N(imine) bond to close an S(6) loop. The minor component of the disordered hy-droxy group forms an O-H⋯N(piperazine) hydrogen bond. These, along with C-H⋯S and C-H⋯N inter-actions, link mol-ecules into a three-dimensional architecture.

Related literature

For the diverse biological activities of adamantane derivatives, see: Vernier et al. (1969 ▶); El-Emam et al. (2004 ▶); Kadi et al. (2007 ▶, 2010 ▶). For related structural studies, see: Kadi et al. (2011 ▶); El-Emam et al. (2012 ▶). For the synthesis of the precursor to the title compound, see: Al-Omar et al. (2010 ▶)

Experimental

Crystal data

C31H38N6OS

M = 542.73

Monoclinic,

a = 10.6015 (5) Å

b = 12.0283 (7) Å

c = 22.7865 (12) Å

β = 101.222 (4)°

V = 2850.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.15 mm−1

T = 100 K

0.40 × 0.40 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.570, T max = 1.000

11447 measured reflections

6530 independent reflections

4526 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.125

S = 1.02

6530 reflections

364 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.29 e Å−3

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/S1600536812021204/qm2068sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021204/qm2068Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021204/qm2068Isup3.cml

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

C31H38N6OS	F(000) = 1160
Mr = 542.73	Dx = 1.265 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3530 reflections
a = 10.6015 (5) Å	θ = 2.3–27.5°
b = 12.0283 (7) Å	µ = 0.15 mm−1
c = 22.7865 (12) Å	T = 100 K
β = 101.222 (4)°	Prism, colourless
V = 2850.1 (3) Å3	0.40 × 0.40 × 0.10 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	6530 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4526 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.032
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.3°
ω scan	h = −13→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→15
Tmin = 0.570, Tmax = 1.000	l = −20→29
11447 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.042P)2 + 0.843P] where P = (Fo2 + 2Fc2)/3
6530 reflections	(Δ/σ)max = 0.001
364 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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	Occ. (<1)
S1	0.26003 (5)	0.62548 (5)	0.73271 (3)	0.03659 (16)
O1	0.67165 (14)	0.49724 (17)	0.61888 (8)	0.0329 (6)	0.762 (3)
H1o	0.6498	0.5466	0.6410	0.049*	0.762 (3)
O1'	0.2282 (5)	0.4574 (5)	0.5670 (3)	0.0324 (18)	0.238 (3)
H1o'	0.1859	0.4049	0.5780	0.049*	0.238 (3)
N1	0.51345 (13)	0.62441 (13)	0.66474 (7)	0.0240 (4)
N2	0.48195 (13)	0.70959 (13)	0.70132 (7)	0.0222 (3)
N3	0.51922 (14)	0.86006 (14)	0.75723 (7)	0.0261 (4)
N4	0.40900 (13)	0.80618 (14)	0.76589 (7)	0.0265 (4)
N5	0.41461 (14)	0.82682 (15)	0.87387 (7)	0.0280 (4)
N6	0.61744 (15)	0.77152 (15)	0.97143 (7)	0.0307 (4)
C1	0.68951 (16)	0.82020 (17)	0.69971 (8)	0.0229 (4)
C2	0.74105 (17)	0.93454 (18)	0.72398 (9)	0.0290 (4)
H2A	0.6806	0.9936	0.7061	0.035*
H2B	0.7479	0.9366	0.7679	0.035*
C3	0.87413 (18)	0.95560 (19)	0.70855 (9)	0.0351 (5)
H3	0.9070	1.0298	0.7245	0.042*
C4	0.8622 (2)	0.9539 (2)	0.64047 (9)	0.0386 (5)
H4A	0.8029	1.0133	0.6221	0.046*
H4B	0.9474	0.9677	0.6302	0.046*
C5	0.81110 (19)	0.84063 (19)	0.61607 (9)	0.0348 (5)
H5	0.8038	0.8395	0.5716	0.042*
C6	0.67807 (17)	0.82016 (18)	0.63125 (8)	0.0278 (4)
H6A	0.6439	0.7477	0.6146	0.033*
H6B	0.6177	0.8792	0.6132	0.033*
C7	0.78629 (16)	0.73016 (18)	0.72866 (9)	0.0281 (4)
H7A	0.7946	0.7321	0.7727	0.034*
H7B	0.7543	0.6557	0.7144	0.034*
C8	0.91771 (17)	0.7508 (2)	0.71237 (10)	0.0364 (5)
H8	0.9793	0.6915	0.7304	0.044*
C9	0.90309 (18)	0.7490 (2)	0.64414 (10)	0.0380 (5)
H9A	0.9881	0.7602	0.6332	0.046*
H9B	0.8695	0.6758	0.6285	0.046*
C10	0.96774 (19)	0.8648 (2)	0.73648 (10)	0.0388 (6)
H10A	0.9768	0.8661	0.7805	0.047*
H10B	1.0534	0.8785	0.7267	0.047*
C11	0.56314 (16)	0.79885 (16)	0.71860 (8)	0.0231 (4)
C12	0.38254 (16)	0.71301 (17)	0.73315 (8)	0.0261 (4)
C13	0.34350 (17)	0.84426 (19)	0.81387 (9)	0.0301 (5)
H13A	0.3250	0.9247	0.8083	0.036*
H13B	0.2601	0.8051	0.8095	0.036*
C14	0.52571 (18)	0.90045 (18)	0.89159 (9)	0.0335 (5)
H14A	0.4996	0.9786	0.8827	0.040*
H14B	0.5932	0.8815	0.8687	0.040*
C15	0.5775 (2)	0.88674 (19)	0.95780 (10)	0.0386 (5)
H15A	0.6520	0.9369	0.9703	0.046*
H15B	0.5103	0.9075	0.9805	0.046*
C16	0.50592 (17)	0.6981 (2)	0.95405 (9)	0.0339 (5)
H16A	0.4395	0.7170	0.9775	0.041*
H16B	0.5323	0.6199	0.9628	0.041*
C17	0.45078 (17)	0.71111 (18)	0.88788 (9)	0.0298 (5)
H17A	0.5154	0.6875	0.8644	0.036*
H17B	0.3742	0.6628	0.8766	0.036*
C18	0.6755 (2)	0.7621 (2)	1.03506 (9)	0.0417 (6)
H18A	0.6078	0.7740	1.0588	0.050*
H18B	0.7399	0.8220	1.0455	0.050*
C19	0.74004 (17)	0.65195 (19)	1.05285 (9)	0.0310 (5)
C20	0.75362 (17)	0.6155 (2)	1.11188 (9)	0.0344 (5)
H20	0.7175	0.6578	1.1397	0.041*
C21	0.81892 (19)	0.5186 (2)	1.13025 (9)	0.0405 (6)
H21	0.8286	0.4956	1.1708	0.049*
C22	0.87039 (19)	0.4547 (2)	1.09039 (10)	0.0410 (6)
H22	0.9145	0.3875	1.1031	0.049*
C23	0.85679 (18)	0.4899 (2)	1.03140 (10)	0.0382 (5)
H23	0.8914	0.4465	1.0035	0.046*
C24	0.79293 (18)	0.5884 (2)	1.01311 (9)	0.0347 (5)
H24	0.7854	0.6125	0.9729	0.042*
C25	0.41941 (16)	0.57102 (17)	0.63287 (8)	0.0248 (4)
H25	0.3335	0.5914	0.6343	0.030*
C26	0.44301 (16)	0.48029 (17)	0.59477 (8)	0.0240 (4)
C27	0.33739 (17)	0.42259 (18)	0.56174 (8)	0.0283 (5)
H27	0.2529	0.4435	0.5654	0.034*	0.762 (3)
C28	0.35374 (19)	0.3367 (2)	0.52428 (9)	0.0359 (5)
H28	0.2811	0.3001	0.5013	0.043*
C29	0.47679 (19)	0.3037 (2)	0.52021 (9)	0.0370 (5)
H29	0.4883	0.2441	0.4944	0.044*
C30	0.58288 (19)	0.35642 (19)	0.55309 (9)	0.0341 (5)
H30	0.6669	0.3317	0.5508	0.041*
C31	0.56677 (17)	0.44516 (18)	0.58934 (8)	0.0276 (4)
H31	0.6401	0.4829	0.6109	0.033*	0.238 (3)

	U11	U22	U33	U12	U13	U23
S1	0.0313 (3)	0.0351 (3)	0.0467 (3)	−0.0086 (2)	0.0159 (2)	−0.0070 (3)
O1	0.0223 (9)	0.0354 (13)	0.0382 (11)	−0.0003 (8)	−0.0007 (7)	−0.0151 (10)
O1'	0.022 (3)	0.035 (4)	0.039 (4)	−0.011 (3)	0.001 (2)	0.004 (3)
N1	0.0281 (8)	0.0193 (9)	0.0243 (8)	0.0006 (7)	0.0045 (6)	−0.0031 (7)
N2	0.0220 (7)	0.0188 (9)	0.0253 (8)	0.0006 (6)	0.0035 (6)	−0.0023 (7)
N3	0.0268 (8)	0.0241 (10)	0.0272 (8)	0.0007 (7)	0.0049 (6)	−0.0011 (8)
N4	0.0265 (8)	0.0235 (10)	0.0303 (9)	0.0012 (7)	0.0077 (6)	−0.0013 (8)
N5	0.0276 (8)	0.0261 (10)	0.0319 (9)	0.0049 (7)	0.0098 (6)	−0.0022 (8)
N6	0.0379 (9)	0.0291 (11)	0.0245 (8)	0.0028 (8)	0.0045 (6)	−0.0043 (8)
C1	0.0238 (9)	0.0221 (11)	0.0226 (9)	−0.0035 (8)	0.0043 (7)	−0.0013 (8)
C2	0.0367 (10)	0.0246 (11)	0.0257 (10)	−0.0061 (9)	0.0060 (8)	−0.0048 (9)
C3	0.0399 (11)	0.0299 (13)	0.0362 (12)	−0.0135 (9)	0.0090 (8)	−0.0107 (10)
C4	0.0456 (12)	0.0371 (14)	0.0355 (12)	−0.0161 (10)	0.0141 (9)	−0.0040 (11)
C5	0.0422 (11)	0.0376 (14)	0.0274 (11)	−0.0156 (10)	0.0133 (8)	−0.0103 (10)
C6	0.0323 (10)	0.0268 (12)	0.0236 (10)	−0.0056 (8)	0.0038 (7)	−0.0013 (9)
C7	0.0250 (9)	0.0281 (12)	0.0294 (10)	−0.0006 (8)	0.0006 (7)	0.0009 (9)
C8	0.0239 (10)	0.0380 (14)	0.0457 (13)	−0.0016 (9)	0.0028 (8)	−0.0058 (11)
C9	0.0290 (10)	0.0391 (14)	0.0495 (13)	−0.0104 (9)	0.0166 (9)	−0.0165 (12)
C10	0.0299 (10)	0.0471 (16)	0.0383 (12)	−0.0105 (10)	0.0041 (8)	−0.0063 (12)
C11	0.0257 (9)	0.0207 (11)	0.0214 (9)	0.0021 (8)	0.0008 (7)	0.0022 (8)
C12	0.0242 (9)	0.0266 (12)	0.0274 (10)	0.0033 (8)	0.0052 (7)	0.0021 (9)
C13	0.0282 (10)	0.0295 (12)	0.0340 (11)	0.0085 (9)	0.0094 (8)	−0.0026 (10)
C14	0.0407 (11)	0.0219 (12)	0.0376 (12)	0.0025 (9)	0.0068 (8)	−0.0055 (10)
C15	0.0472 (12)	0.0302 (13)	0.0372 (12)	0.0036 (10)	0.0055 (9)	−0.0079 (11)
C16	0.0319 (10)	0.0371 (14)	0.0354 (11)	0.0039 (9)	0.0134 (8)	0.0050 (11)
C17	0.0265 (9)	0.0278 (12)	0.0356 (11)	−0.0005 (8)	0.0074 (8)	−0.0021 (10)
C18	0.0562 (13)	0.0440 (16)	0.0245 (11)	0.0063 (11)	0.0072 (9)	−0.0062 (11)
C19	0.0303 (10)	0.0360 (13)	0.0270 (10)	−0.0021 (9)	0.0061 (7)	−0.0032 (10)
C20	0.0299 (10)	0.0482 (15)	0.0255 (10)	−0.0077 (10)	0.0064 (8)	−0.0057 (11)
C21	0.0436 (12)	0.0486 (16)	0.0270 (11)	−0.0115 (11)	0.0015 (9)	0.0031 (11)
C22	0.0397 (12)	0.0388 (15)	0.0405 (13)	−0.0021 (10)	−0.0019 (9)	0.0027 (12)
C23	0.0368 (11)	0.0407 (15)	0.0376 (12)	−0.0005 (10)	0.0088 (9)	−0.0040 (11)
C24	0.0377 (11)	0.0416 (14)	0.0262 (10)	−0.0008 (10)	0.0097 (8)	−0.0006 (10)
C25	0.0248 (9)	0.0248 (11)	0.0235 (9)	−0.0002 (8)	0.0020 (7)	0.0033 (9)
C26	0.0292 (9)	0.0205 (11)	0.0217 (9)	−0.0020 (8)	0.0037 (7)	0.0014 (8)
C27	0.0283 (10)	0.0304 (12)	0.0254 (10)	−0.0076 (8)	0.0035 (7)	0.0021 (9)
C28	0.0397 (11)	0.0362 (13)	0.0307 (11)	−0.0144 (10)	0.0041 (8)	−0.0065 (11)
C29	0.0477 (12)	0.0324 (13)	0.0322 (11)	−0.0070 (10)	0.0107 (9)	−0.0106 (11)
C30	0.0372 (11)	0.0314 (13)	0.0344 (11)	−0.0005 (9)	0.0090 (8)	−0.0060 (10)
C31	0.0300 (10)	0.0258 (11)	0.0259 (10)	−0.0032 (8)	0.0026 (7)	−0.0008 (9)

S1—C12	1.670 (2)	C9—H9A	0.9900
O1—C31	1.338 (2)	C9—H9B	0.9900
O1—H1o	0.8400	C10—H10A	0.9900
O1'—C27	1.259 (6)	C10—H10B	0.9900
O1'—H1o'	0.8400	C13—H13A	0.9900
N1—C25	1.285 (2)	C13—H13B	0.9900
N1—N2	1.402 (2)	C14—C15	1.511 (3)
N2—C11	1.384 (2)	C14—H14A	0.9900
N2—C12	1.391 (2)	C14—H14B	0.9900
N3—C11	1.301 (2)	C15—H15A	0.9900
N3—N4	1.384 (2)	C15—H15B	0.9900
N4—C12	1.345 (3)	C16—C17	1.515 (3)
N4—C13	1.477 (2)	C16—H16A	0.9900
N5—C13	1.442 (2)	C16—H16B	0.9900
N5—C17	1.462 (3)	C17—H17A	0.9900
N5—C14	1.466 (3)	C17—H17B	0.9900
N6—C18	1.465 (3)	C18—C19	1.509 (3)
N6—C15	1.465 (3)	C18—H18A	0.9900
N6—C16	1.467 (3)	C18—H18B	0.9900
C1—C11	1.507 (2)	C19—C24	1.384 (3)
C1—C6	1.541 (3)	C19—C20	1.395 (3)
C1—C2	1.542 (3)	C20—C21	1.378 (3)
C1—C7	1.548 (3)	C20—H20	0.9500
C2—C3	1.540 (3)	C21—C22	1.381 (3)
C2—H2A	0.9900	C21—H21	0.9500
C2—H2B	0.9900	C22—C23	1.390 (3)
C3—C10	1.529 (3)	C22—H22	0.9500
C3—C4	1.532 (3)	C23—C24	1.387 (3)
C3—H3	1.0000	C23—H23	0.9500
C4—C5	1.530 (3)	C24—H24	0.9500
C4—H4A	0.9900	C25—C26	1.446 (3)
C4—H4B	0.9900	C25—H25	0.9500
C5—C9	1.527 (3)	C26—C27	1.405 (3)
C5—C6	1.536 (2)	C26—C31	1.407 (2)
C5—H5	1.0000	C27—C28	1.373 (3)
C6—H6A	0.9900	C27—H27	0.9500
C6—H6B	0.9900	C28—C29	1.384 (3)
C7—C8	1.530 (3)	C28—H28	0.9500
C7—H7A	0.9900	C29—C30	1.378 (3)
C7—H7B	0.9900	C29—H29	0.9500
C8—C10	1.533 (3)	C30—C31	1.381 (3)
C8—C9	1.532 (3)	C30—H30	0.9500
C8—H8	1.0000	C31—H31	0.9500
C31—O1—H1o	109.5	N2—C12—S1	130.17 (15)
C27—O1'—H1o'	109.5	N5—C13—N4	114.97 (15)
C25—N1—N2	116.93 (15)	N5—C13—H13A	108.5
C11—N2—C12	108.71 (15)	N4—C13—H13A	108.5
C11—N2—N1	121.94 (14)	N5—C13—H13B	108.5
C12—N2—N1	128.61 (15)	N4—C13—H13B	108.5
C11—N3—N4	104.76 (15)	H13A—C13—H13B	107.5
C12—N4—N3	113.70 (14)	N5—C14—C15	109.01 (18)
C12—N4—C13	126.25 (16)	N5—C14—H14A	109.9
N3—N4—C13	119.47 (16)	C15—C14—H14A	109.9
C13—N5—C17	114.32 (17)	N5—C14—H14B	109.9
C13—N5—C14	114.64 (17)	C15—C14—H14B	109.9
C17—N5—C14	110.63 (15)	H14A—C14—H14B	108.3
C18—N6—C15	109.38 (17)	N6—C15—C14	110.42 (18)
C18—N6—C16	112.46 (17)	N6—C15—H15A	109.6
C15—N6—C16	109.15 (16)	C14—C15—H15A	109.6
C11—C1—C6	112.95 (14)	N6—C15—H15B	109.6
C11—C1—C2	108.80 (15)	C14—C15—H15B	109.6
C6—C1—C2	108.42 (16)	H15A—C15—H15B	108.1
C11—C1—C7	108.15 (15)	N6—C16—C17	109.94 (17)
C6—C1—C7	110.25 (16)	N6—C16—H16A	109.7
C2—C1—C7	108.17 (15)	C17—C16—H16A	109.7
C3—C2—C1	109.95 (16)	N6—C16—H16B	109.7
C3—C2—H2A	109.7	C17—C16—H16B	109.7
C1—C2—H2A	109.7	H16A—C16—H16B	108.2
C3—C2—H2B	109.7	N5—C17—C16	110.46 (18)
C1—C2—H2B	109.7	N5—C17—H17A	109.6
H2A—C2—H2B	108.2	C16—C17—H17A	109.6
C10—C3—C4	109.31 (18)	N5—C17—H17B	109.6
C10—C3—C2	109.67 (18)	C16—C17—H17B	109.6
C4—C3—C2	109.30 (16)	H17A—C17—H17B	108.1
C10—C3—H3	109.5	N6—C18—C19	114.52 (18)
C4—C3—H3	109.5	N6—C18—H18A	108.6
C2—C3—H3	109.5	C19—C18—H18A	108.6
C5—C4—C3	109.49 (18)	N6—C18—H18B	108.6
C5—C4—H4A	109.8	C19—C18—H18B	108.6
C3—C4—H4A	109.8	H18A—C18—H18B	107.6
C5—C4—H4B	109.8	C24—C19—C20	118.6 (2)
C3—C4—H4B	109.8	C24—C19—C18	121.94 (19)
H4A—C4—H4B	108.2	C20—C19—C18	119.41 (19)
C9—C5—C4	109.74 (17)	C21—C20—C19	120.7 (2)
C9—C5—C6	109.24 (17)	C21—C20—H20	119.7
C4—C5—C6	109.68 (17)	C19—C20—H20	119.7
C9—C5—H5	109.4	C20—C21—C22	120.7 (2)
C4—C5—H5	109.4	C20—C21—H21	119.6
C6—C5—H5	109.4	C22—C21—H21	119.6
C5—C6—C1	109.46 (15)	C21—C22—C23	119.1 (2)
C5—C6—H6A	109.8	C21—C22—H22	120.5
C1—C6—H6A	109.8	C23—C22—H22	120.5
C5—C6—H6B	109.8	C24—C23—C22	120.2 (2)
C1—C6—H6B	109.8	C24—C23—H23	119.9
H6A—C6—H6B	108.2	C22—C23—H23	119.9
C8—C7—C1	110.02 (17)	C19—C24—C23	120.7 (2)
C8—C7—H7A	109.7	C19—C24—H24	119.6
C1—C7—H7A	109.7	C23—C24—H24	119.6
C8—C7—H7B	109.7	N1—C25—C26	120.69 (16)
C1—C7—H7B	109.7	N1—C25—H25	119.7
H7A—C7—H7B	108.2	C26—C25—H25	119.7
C7—C8—C10	109.03 (17)	C27—C26—C31	117.66 (18)
C7—C8—C9	109.07 (15)	C27—C26—C25	118.77 (16)
C10—C8—C9	109.61 (19)	C31—C26—C25	123.56 (16)
C7—C8—H8	109.7	O1'—C27—C28	122.6 (3)
C10—C8—H8	109.7	O1'—C27—C26	115.9 (3)
C9—C8—H8	109.7	C28—C27—C26	121.40 (18)
C5—C9—C8	110.21 (18)	C28—C27—H27	119.3
C5—C9—H9A	109.6	C26—C27—H27	119.3
C8—C9—H9A	109.6	C27—C28—C29	119.47 (18)
C5—C9—H9B	109.6	C27—C28—H28	120.3
C8—C9—H9B	109.6	C29—C28—H28	120.3
H9A—C9—H9B	108.1	C30—C29—C28	120.8 (2)
C3—C10—C8	109.80 (16)	C30—C29—H29	119.6
C3—C10—H10A	109.7	C28—C29—H29	119.6
C8—C10—H10A	109.7	C31—C30—C29	119.85 (19)
C3—C10—H10B	109.7	C31—C30—H30	120.1
C8—C10—H10B	109.7	C29—C30—H30	120.1
H10A—C10—H10B	108.2	O1—C31—C30	118.39 (18)
N3—C11—N2	110.28 (16)	O1—C31—C26	120.87 (19)
N3—C11—C1	123.49 (17)	C30—C31—C26	120.74 (17)
N2—C11—C1	126.09 (17)	C30—C31—H31	119.6
N4—C12—N2	102.50 (15)	C26—C31—H31	119.6
N4—C12—S1	127.33 (14)
C25—N1—N2—C11	−153.92 (17)	C11—N2—C12—N4	1.88 (19)
C25—N1—N2—C12	37.0 (3)	N1—N2—C12—N4	172.08 (16)
C11—N3—N4—C12	−0.5 (2)	C11—N2—C12—S1	−177.78 (15)
C11—N3—N4—C13	171.33 (16)	N1—N2—C12—S1	−7.6 (3)
C11—C1—C2—C3	176.65 (15)	C17—N5—C13—N4	−57.1 (2)
C6—C1—C2—C3	−60.2 (2)	C14—N5—C13—N4	72.1 (2)
C7—C1—C2—C3	59.4 (2)	C12—N4—C13—N5	103.4 (2)
C1—C2—C3—C10	−59.7 (2)	N3—N4—C13—N5	−67.3 (2)
C1—C2—C3—C4	60.1 (2)	C13—N5—C14—C15	170.69 (16)
C10—C3—C4—C5	60.4 (2)	C17—N5—C14—C15	−58.3 (2)
C2—C3—C4—C5	−59.7 (2)	C18—N6—C15—C14	176.07 (17)
C3—C4—C5—C9	−59.7 (2)	C16—N6—C15—C14	−60.5 (2)
C3—C4—C5—C6	60.3 (2)	N5—C14—C15—N6	60.0 (2)
C9—C5—C6—C1	59.5 (2)	C18—N6—C16—C17	−179.65 (17)
C4—C5—C6—C1	−60.8 (2)	C15—N6—C16—C17	58.8 (2)
C11—C1—C6—C5	−179.12 (17)	C13—N5—C17—C16	−171.07 (15)
C2—C1—C6—C5	60.2 (2)	C14—N5—C17—C16	57.7 (2)
C7—C1—C6—C5	−58.0 (2)	N6—C16—C17—N5	−57.8 (2)
C11—C1—C7—C8	−178.13 (16)	C15—N6—C18—C19	−170.56 (18)
C6—C1—C7—C8	57.9 (2)	C16—N6—C18—C19	68.0 (2)
C2—C1—C7—C8	−60.5 (2)	N6—C18—C19—C24	28.6 (3)
C1—C7—C8—C10	61.0 (2)	N6—C18—C19—C20	−155.13 (18)
C1—C7—C8—C9	−58.6 (2)	C24—C19—C20—C21	0.4 (3)
C4—C5—C9—C8	58.9 (2)	C18—C19—C20—C21	−176.06 (19)
C6—C5—C9—C8	−61.4 (2)	C19—C20—C21—C22	−1.1 (3)
C7—C8—C9—C5	60.9 (2)	C20—C21—C22—C23	0.7 (3)
C10—C8—C9—C5	−58.4 (2)	C21—C22—C23—C24	0.3 (3)
C4—C3—C10—C8	−60.2 (2)	C20—C19—C24—C23	0.7 (3)
C2—C3—C10—C8	59.6 (2)	C18—C19—C24—C23	177.0 (2)
C7—C8—C10—C3	−60.3 (2)	C22—C23—C24—C19	−1.1 (3)
C9—C8—C10—C3	59.1 (2)	N2—N1—C25—C26	−178.69 (16)
N4—N3—C11—N2	1.70 (19)	N1—C25—C26—C27	178.57 (18)
N4—N3—C11—C1	−174.38 (16)	N1—C25—C26—C31	−0.6 (3)
C12—N2—C11—N3	−2.4 (2)	C31—C26—C27—O1'	−179.0 (3)
N1—N2—C11—N3	−173.33 (15)	C25—C26—C27—O1'	1.8 (4)
C12—N2—C11—C1	173.59 (17)	C31—C26—C27—C28	−1.6 (3)
N1—N2—C11—C1	2.6 (3)	C25—C26—C27—C28	179.19 (19)
C6—C1—C11—N3	−130.8 (2)	O1'—C27—C28—C29	179.2 (4)
C2—C1—C11—N3	−10.4 (2)	C26—C27—C28—C29	2.0 (3)
C7—C1—C11—N3	106.9 (2)	C27—C28—C29—C30	−0.3 (3)
C6—C1—C11—N2	53.8 (3)	C28—C29—C30—C31	−1.8 (3)
C2—C1—C11—N2	174.19 (17)	C29—C30—C31—O1	−177.4 (2)
C7—C1—C11—N2	−68.5 (2)	C29—C30—C31—C26	2.2 (3)
N3—N4—C12—N2	−0.9 (2)	C27—C26—C31—O1	179.11 (19)
C13—N4—C12—N2	−172.05 (16)	C25—C26—C31—O1	−1.7 (3)
N3—N4—C12—S1	178.77 (14)	C27—C26—C31—C30	−0.5 (3)
C13—N4—C12—S1	7.6 (3)	C25—C26—C31—C30	178.67 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.84	1.89	2.632 (2)	147
O1′—H1o′···N5i	0.84	1.92	2.714 (6)	158
C13—H13A···S1ii	0.99	2.68	3.650 (2)	166
C30—H30···N6iii	0.95	2.54	3.484 (3)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.84	1.89	2.632 (2)	147
O1′—H1o′⋯N5i	0.84	1.92	2.714 (6)	158
C13—H13A⋯S1ii	0.99	2.68	3.650 (2)	166
C30—H30⋯N6iii	0.95	2.54	3.484 (3)	172

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