3-(Adamantan-1-yl)-4-phenyl-1-[(4-phenyl-piperazin-1-yl)meth-yl]-1H-1,2,4-triazole-5(4H)-thione.

The title mol-ecule, C(29)H(35)N(5)S, displays a chair-shaped piperazine ring, as well as an approximately planar triazole ring (r.m.s. deviation = 0.001 Å) whose phenyl substituent is nearly perpendicular to the mean plane of the five-membered ring [dihedral angle = 88.9 (1)°]. The substituents on the piperazine ring occupy equatorial sites. In the crystal, the adamantyl cage is disordered over two sets of sites with a major component of 67.8 (5)%. Weak inter-molecular C-H⋯S hydrogen bonding is present in the crystal.

Related literature

For the synthesis and applications of 3-(1-adamant­yl)-4-substituted-5-mercapto-1,2,4-triazole derivatives, see: El-Emam & Ibrahim (1991 ▶).

Experimental

Crystal data

C29H35N5S

M = 485.68

Monoclinic,

a = 11.3342 (5) Å

b = 8.4744 (3) Å

c = 13.7868 (6) Å

β = 103.864 (4)°

V = 1285.65 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.15 mm−1

T = 100 K

0.40 × 0.35 × 0.30 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.941, T max = 0.956

8952 measured reflections

5539 independent reflections

5155 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.154

S = 1.02

5537 reflections

398 parameters

169 restraints

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.56 e Å−3

Absolute structure: Flack (1983 ▶), 2382 Friedel pairs

Flack parameter: 0.01 (11)

Data collection: CrysAlis PRO (Agilent, 2010 ▶); 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811055711/xu5420sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055711/xu5420Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055711/xu5420Isup3.cml

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

C29H35N5S	F(000) = 520
Mr = 485.68	Dx = 1.255 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5784 reflections
a = 11.3342 (5) Å	θ = 2.4–27.5°
b = 8.4744 (3) Å	µ = 0.15 mm−1
c = 13.7868 (6) Å	T = 100 K
β = 103.864 (4)°	Wedge, colorless
V = 1285.65 (9) Å3	0.40 × 0.35 × 0.30 mm
Z = 2

Agilent SuperNova Dual diffractometer with an Atlas detector	5539 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	5155 reflections with I > 2σ(I)
Mirror	Rint = 0.022
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.8°
ω scan	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −10→11
Tmin = 0.941, Tmax = 0.956	l = −13→17
8952 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)] = 0.060	H-atom parameters constrained
wR(F2) = 0.154	w = 1/[σ2(Fo2) + (0.0713P)2 + 1.5877P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
5537 reflections	Δρmax = 0.72 e Å−3
398 parameters	Δρmin = −0.56 e Å−3
169 restraints	Absolute structure: Flack (1983), 2382 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (11)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.82856 (7)	0.50082 (16)	0.02316 (5)	0.02700 (18)
N1	0.8127 (2)	0.7494 (3)	0.14650 (19)	0.0224 (5)
N2	1.0027 (2)	0.8295 (4)	0.1988 (2)	0.0281 (6)
N3	0.9950 (2)	0.7016 (3)	0.1347 (2)	0.0253 (6)
N4	1.1767 (2)	0.5280 (4)	0.1622 (2)	0.0254 (6)
N5	1.2418 (2)	0.2718 (4)	0.29827 (19)	0.0244 (6)
C1	0.8801 (3)	0.6498 (4)	0.1015 (2)	0.0224 (6)
C2	0.8918 (3)	0.8563 (4)	0.2051 (2)	0.0246 (6)
C3	0.6821 (3)	0.7415 (4)	0.1239 (3)	0.0297 (7)
C4	0.6262 (4)	0.6461 (5)	0.1808 (3)	0.0438 (10)
H4	0.6729	0.5857	0.2345	0.053*
C5	0.4988 (4)	0.6406 (6)	0.1573 (5)	0.0613 (15)
H5	0.4586	0.5758	0.1956	0.074*
C6	0.4320 (4)	0.7274 (6)	0.0803 (5)	0.0637 (15)
H6	0.3458	0.7228	0.0653	0.076*
C7	0.4887 (4)	0.8215 (6)	0.0240 (5)	0.0593 (14)
H7	0.4416	0.8820	−0.0294	0.071*
C8	0.6154 (3)	0.8283 (5)	0.0452 (3)	0.0404 (9)
H8	0.6550	0.8920	0.0059	0.049*
C9	0.8586 (2)	0.9902 (3)	0.2700 (2)	0.0366 (8)
C10	0.7951 (4)	1.1115 (4)	0.1942 (2)	0.0408 (14)	0.678 (5)
H10A	0.8508	1.1462	0.1530	0.049*	0.678 (5)
H10B	0.7228	1.0630	0.1493	0.049*	0.678 (5)
C11	0.7569 (4)	1.2516 (4)	0.2460 (3)	0.0391 (13)	0.678 (5)
H11	0.7171	1.3314	0.1952	0.047*	0.678 (5)
C12	0.8665 (4)	1.3237 (4)	0.3151 (3)	0.0433 (17)	0.678 (5)
H12A	0.9237	1.3619	0.2761	0.052*	0.678 (5)
H12B	0.8416	1.4149	0.3504	0.052*	0.678 (5)
C13	0.9280 (3)	1.2023 (4)	0.3896 (3)	0.0424 (16)	0.678 (5)
H13	1.0006	1.2506	0.4358	0.051*	0.678 (5)
C14	0.9677 (3)	1.0649 (5)	0.3362 (3)	0.0434 (16)	0.678 (5)
H14A	1.0238	1.1016	0.2959	0.052*	0.678 (5)
H14B	1.0112	0.9869	0.3855	0.052*	0.678 (5)
C15	0.6689 (3)	1.1999 (5)	0.3060 (3)	0.0374 (13)	0.678 (5)
H15A	0.5951	1.1551	0.2611	0.045*	0.678 (5)
H15B	0.6446	1.2916	0.3413	0.045*	0.678 (5)
C16	0.7294 (3)	1.0775 (4)	0.3804 (3)	0.0303 (12)	0.678 (5)
H16	0.6715	1.0419	0.4204	0.036*	0.678 (5)
C17	0.8409 (4)	1.1462 (5)	0.4491 (2)	0.0377 (13)	0.678 (5)
H17A	0.8175	1.2357	0.4867	0.045*	0.678 (5)
H17B	0.8807	1.0652	0.4977	0.045*	0.678 (5)
C18	0.7658 (3)	0.9387 (3)	0.3261 (3)	0.0261 (11)	0.678 (5)
H18A	0.6934	0.8951	0.2786	0.031*	0.678 (5)
H18B	0.8007	0.8549	0.3745	0.031*	0.678 (5)
C19	1.1068 (3)	0.6541 (5)	0.1049 (3)	0.0280 (7)
H19A	1.0839	0.6214	0.0339	0.034*
H19B	1.1599	0.7478	0.1095	0.034*
C20	1.2026 (3)	0.5548 (4)	0.2700 (2)	0.0264 (7)
H20A	1.1261	0.5502	0.2926	0.032*
H20B	1.2384	0.6610	0.2858	0.032*
C21	1.2901 (3)	0.4310 (4)	0.3246 (3)	0.0271 (7)
H21A	1.3693	0.4423	0.3067	0.033*
H21B	1.3037	0.4469	0.3976	0.033*
C22	1.2169 (3)	0.2464 (4)	0.1899 (2)	0.0283 (7)
H22A	1.1828	0.1395	0.1733	0.034*
H22B	1.2933	0.2546	0.1674	0.034*
C23	1.1266 (3)	0.3703 (4)	0.1372 (2)	0.0241 (6)
H23A	1.1094	0.3543	0.0640	0.029*
H23B	1.0493	0.3595	0.1580	0.029*
C24	1.3055 (3)	0.1486 (4)	0.3583 (2)	0.0220 (6)
C25	1.3170 (3)	0.1532 (4)	0.4616 (2)	0.0295 (7)
H25	1.2840	0.2397	0.4902	0.035*
C26	1.3757 (3)	0.0341 (5)	0.5226 (2)	0.0327 (8)
H26	1.3825	0.0393	0.5925	0.039*
C27	1.4254 (3)	−0.0945 (4)	0.4823 (3)	0.0314 (7)
H27	1.4663	−0.1761	0.5244	0.038*
C28	1.4139 (3)	−0.1007 (5)	0.3811 (3)	0.0313 (7)
H28	1.4466	−0.1881	0.3531	0.038*
C29	1.3552 (3)	0.0193 (4)	0.3184 (2)	0.0267 (6)
H29	1.3488	0.0134	0.2485	0.032*
C10'	0.9726 (4)	1.0898 (7)	0.2942 (5)	0.041 (3)	0.322 (5)
H10C	1.0445	1.0199	0.3129	0.050*	0.322 (5)
H10D	0.9787	1.1499	0.2340	0.050*	0.322 (5)
C11'	0.9728 (5)	1.2025 (6)	0.3780 (4)	0.037 (3)	0.322 (5)
H11B	1.0480	1.2687	0.3899	0.045*	0.322 (5)
C12'	0.9704 (5)	1.1144 (8)	0.4720 (4)	0.041 (3)	0.322 (5)
H12C	0.9674	1.1897	0.5263	0.049*	0.322 (5)
H12D	1.0445	1.0492	0.4933	0.049*	0.322 (5)
C13'	0.8595 (5)	1.0112 (6)	0.4507 (3)	0.030 (2)	0.322 (5)
H13'	0.8571	0.9485	0.5116	0.036*	0.322 (5)
C14'	0.8619 (6)	0.9014 (5)	0.3658 (3)	0.034 (3)	0.322 (5)
H14C	0.7912	0.8294	0.3553	0.041*	0.322 (5)
H14D	0.9366	0.8364	0.3832	0.041*	0.322 (5)
C15'	0.8633 (6)	1.3077 (5)	0.3507 (6)	0.037 (4)	0.322 (5)
H15C	0.8626	1.3817	0.4061	0.045*	0.322 (5)
H15D	0.8657	1.3702	0.2905	0.045*	0.322 (5)
C16'	0.7514 (5)	1.2067 (5)	0.3305 (4)	0.027 (2)	0.322 (5)
H16'	0.6780	1.2760	0.3129	0.032*	0.322 (5)
C17'	0.7481 (5)	1.1129 (8)	0.4221 (4)	0.021 (2)	0.322 (5)
H17C	0.6744	1.0459	0.4088	0.025*	0.322 (5)
H17D	0.7448	1.1853	0.4778	0.025*	0.322 (5)
C18'	0.7507 (4)	1.0967 (6)	0.2452 (4)	0.029 (2)	0.322 (5)
H18C	0.6754	1.0329	0.2312	0.035*	0.322 (5)
H18D	0.7521	1.1585	0.1846	0.035*	0.322 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0281 (4)	0.0282 (4)	0.0246 (3)	−0.0012 (3)	0.0061 (3)	0.0004 (3)
N1	0.0228 (12)	0.0208 (13)	0.0263 (13)	0.0058 (10)	0.0115 (10)	0.0054 (10)
N2	0.0273 (13)	0.0260 (14)	0.0299 (14)	0.0066 (11)	0.0044 (11)	−0.0023 (11)
N3	0.0204 (12)	0.0262 (14)	0.0293 (14)	0.0050 (11)	0.0062 (10)	−0.0020 (11)
N4	0.0222 (12)	0.0271 (15)	0.0279 (13)	0.0022 (11)	0.0077 (10)	0.0019 (11)
N5	0.0290 (13)	0.0241 (13)	0.0196 (12)	0.0017 (11)	0.0050 (10)	−0.0029 (10)
C1	0.0254 (14)	0.0236 (15)	0.0195 (13)	0.0044 (12)	0.0080 (11)	0.0064 (12)
C2	0.0282 (15)	0.0243 (16)	0.0229 (14)	0.0048 (13)	0.0092 (12)	0.0059 (12)
C3	0.0234 (15)	0.0252 (17)	0.0460 (19)	0.0028 (13)	0.0191 (14)	0.0057 (14)
C4	0.043 (2)	0.038 (2)	0.062 (3)	0.0016 (18)	0.0353 (19)	0.0087 (19)
C5	0.050 (3)	0.042 (3)	0.112 (4)	−0.014 (2)	0.061 (3)	−0.008 (3)
C6	0.0262 (19)	0.044 (3)	0.130 (5)	0.0000 (19)	0.035 (3)	−0.008 (3)
C7	0.0249 (18)	0.040 (2)	0.109 (4)	0.0076 (18)	0.008 (2)	0.011 (3)
C8	0.0251 (17)	0.034 (2)	0.063 (3)	0.0058 (15)	0.0117 (16)	0.0174 (18)
C9	0.055 (2)	0.0231 (16)	0.0432 (18)	−0.0005 (17)	0.0344 (17)	0.0007 (16)
C10	0.052 (3)	0.025 (3)	0.050 (3)	0.007 (2)	0.023 (3)	−0.004 (2)
C11	0.060 (3)	0.024 (3)	0.038 (3)	0.007 (2)	0.023 (3)	0.001 (2)
C12	0.063 (4)	0.016 (3)	0.062 (4)	−0.006 (3)	0.038 (3)	−0.004 (3)
C13	0.050 (4)	0.038 (3)	0.048 (3)	0.006 (3)	0.029 (3)	−0.017 (3)
C14	0.040 (3)	0.054 (4)	0.030 (3)	0.011 (3)	−0.004 (2)	−0.019 (3)
C15	0.041 (3)	0.033 (3)	0.041 (3)	0.011 (2)	0.016 (2)	−0.008 (2)
C16	0.033 (3)	0.035 (3)	0.026 (3)	−0.002 (2)	0.014 (2)	−0.004 (2)
C17	0.046 (3)	0.036 (3)	0.033 (3)	−0.003 (3)	0.012 (2)	−0.002 (2)
C18	0.030 (2)	0.026 (2)	0.026 (2)	0.0007 (19)	0.0130 (19)	0.0026 (17)
C19	0.0216 (14)	0.0293 (17)	0.0351 (17)	0.0068 (13)	0.0109 (13)	0.0053 (14)
C20	0.0272 (15)	0.0232 (15)	0.0280 (16)	−0.0008 (12)	0.0052 (12)	−0.0068 (12)
C21	0.0256 (15)	0.0261 (16)	0.0279 (16)	−0.0018 (13)	0.0029 (12)	−0.0019 (12)
C22	0.0374 (17)	0.0249 (16)	0.0215 (15)	0.0071 (14)	0.0050 (13)	−0.0010 (12)
C23	0.0283 (15)	0.0235 (16)	0.0194 (14)	0.0037 (13)	0.0035 (11)	−0.0025 (12)
C24	0.0175 (13)	0.0237 (15)	0.0236 (14)	−0.0036 (12)	0.0028 (11)	−0.0018 (12)
C25	0.0301 (16)	0.0308 (17)	0.0278 (16)	0.0007 (14)	0.0071 (13)	−0.0021 (13)
C26	0.0306 (16)	0.042 (2)	0.0238 (15)	−0.0086 (15)	0.0025 (12)	0.0020 (13)
C27	0.0246 (15)	0.0306 (18)	0.0369 (18)	−0.0032 (14)	0.0036 (13)	0.0109 (14)
C28	0.0275 (16)	0.0262 (17)	0.0398 (19)	0.0012 (14)	0.0075 (14)	0.0020 (14)
C29	0.0238 (14)	0.0274 (17)	0.0294 (15)	−0.0007 (14)	0.0074 (11)	−0.0002 (13)
C10'	0.052 (5)	0.041 (5)	0.031 (5)	0.018 (4)	0.009 (4)	−0.019 (4)
C11'	0.042 (5)	0.040 (5)	0.036 (5)	0.017 (4)	0.020 (4)	0.005 (4)
C12'	0.040 (5)	0.039 (5)	0.047 (5)	0.004 (4)	0.016 (4)	0.007 (4)
C13'	0.030 (4)	0.027 (4)	0.036 (4)	0.001 (4)	0.011 (3)	0.003 (4)
C14'	0.035 (4)	0.028 (4)	0.044 (4)	−0.005 (4)	0.020 (4)	0.000 (4)
C15'	0.042 (5)	0.034 (5)	0.036 (5)	0.003 (4)	0.009 (4)	−0.002 (4)
C16'	0.017 (4)	0.027 (4)	0.033 (4)	0.004 (3)	−0.003 (3)	0.000 (3)
C17'	0.021 (4)	0.022 (4)	0.025 (4)	0.000 (3)	0.015 (3)	0.002 (3)
C18'	0.035 (4)	0.032 (4)	0.022 (4)	−0.006 (3)	0.011 (3)	0.001 (3)

S1—C1	1.673 (3)	C17—H17A	0.9900
N1—C1	1.381 (4)	C17—H17B	0.9900
N1—C2	1.390 (4)	C18—H18A	0.9900
N1—C3	1.439 (4)	C18—H18B	0.9900
N2—C2	1.301 (4)	C19—H19A	0.9900
N2—N3	1.387 (4)	C19—H19B	0.9900
N3—C1	1.347 (4)	C20—C21	1.514 (5)
N3—C19	1.478 (4)	C20—H20A	0.9900
N4—C19	1.447 (4)	C20—H20B	0.9900
N4—C20	1.462 (4)	C21—H21A	0.9900
N4—C23	1.460 (4)	C21—H21B	0.9900
N5—C24	1.418 (4)	C22—C23	1.525 (4)
N5—C21	1.468 (4)	C22—H22A	0.9900
N5—C22	1.468 (4)	C22—H22B	0.9900
C2—C9	1.546 (4)	C23—H23A	0.9900
C3—C4	1.382 (5)	C23—H23B	0.9900
C3—C8	1.378 (5)	C24—C25	1.400 (4)
C4—C5	1.403 (6)	C24—C29	1.403 (5)
C4—H4	0.9500	C25—C26	1.378 (5)
C5—C6	1.363 (8)	C25—H25	0.9500
C5—H5	0.9500	C26—C27	1.401 (5)
C6—C7	1.375 (7)	C26—H26	0.9500
C6—H6	0.9500	C27—C28	1.372 (5)
C7—C8	1.396 (5)	C27—H27	0.9500
C7—H7	0.9500	C28—C29	1.396 (5)
C8—H8	0.9500	C28—H28	0.9500
C9—C14	1.491 (2)	C29—H29	0.9500
C9—C18'	1.492 (2)	C10'—C11'	1.499 (2)
C9—C18	1.5111 (19)	C10'—H10C	0.9900
C9—C10'	1.512 (2)	C10'—H10D	0.9900
C9—C14'	1.512 (2)	C11'—C15'	1.501 (2)
C9—C10	1.518 (2)	C11'—C12'	1.501 (2)
C10—C11	1.503 (2)	C11'—H11B	1.0000
C10—H10A	0.9900	C12'—C13'	1.502 (2)
C10—H10B	0.9900	C12'—H12C	0.9900
C11—C12	1.502 (2)	C12'—H12D	0.9900
C11—C15	1.504 (2)	C13'—C14'	1.501 (2)
C11—H11	1.0000	C13'—C17'	1.501 (2)
C12—C13	1.502 (2)	C13'—H13'	1.0000
C12—H12A	0.9900	C14'—H14C	0.9900
C12—H12B	0.9900	C14'—H14D	0.9900
C13—C17	1.503 (2)	C15'—C16'	1.500 (2)
C13—C14	1.503 (2)	C15'—H15C	0.9900
C13—H13	1.0000	C15'—H15D	0.9900
C14—H14A	0.9900	C16'—C18'	1.499 (2)
C14—H14B	0.9900	C16'—C17'	1.501 (2)
C15—C16	1.504 (2)	C16'—H16'	1.0000
C15—H15A	0.9900	C17'—H17C	0.9900
C15—H15B	0.9900	C17'—H17D	0.9900
C16—C17	1.502 (2)	C18'—H18C	0.9900
C16—C18	1.505 (2)	C18'—H18D	0.9900
C16—H16	1.0000
C1—N1—C2	108.1 (2)	H18A—C18—H18B	108.2
C1—N1—C3	121.7 (3)	N4—C19—N3	116.3 (3)
C2—N1—C3	130.0 (3)	N4—C19—H19A	108.2
C2—N2—N3	105.4 (3)	N3—C19—H19A	108.2
C1—N3—N2	112.3 (2)	N4—C19—H19B	108.2
C1—N3—C19	129.8 (3)	N3—C19—H19B	108.2
N2—N3—C19	117.6 (3)	H19A—C19—H19B	107.4
C19—N4—C20	113.0 (3)	N4—C20—C21	110.2 (3)
C19—N4—C23	114.5 (3)	N4—C20—H20A	109.6
C20—N4—C23	110.8 (2)	C21—C20—H20A	109.6
C24—N5—C21	115.1 (2)	N4—C20—H20B	109.6
C24—N5—C22	115.6 (3)	C21—C20—H20B	109.6
C21—N5—C22	110.9 (3)	H20A—C20—H20B	108.1
N3—C1—N1	104.0 (3)	N5—C21—C20	110.6 (3)
N3—C1—S1	128.7 (2)	N5—C21—H21A	109.5
N1—C1—S1	127.3 (2)	C20—C21—H21A	109.5
N2—C2—N1	110.2 (3)	N5—C21—H21B	109.5
N2—C2—C9	122.7 (3)	C20—C21—H21B	109.5
N1—C2—C9	127.1 (3)	H21A—C21—H21B	108.1
C4—C3—C8	121.3 (3)	N5—C22—C23	109.1 (3)
C4—C3—N1	119.5 (3)	N5—C22—H22A	109.9
C8—C3—N1	119.2 (3)	C23—C22—H22A	109.9
C3—C4—C5	118.4 (4)	N5—C22—H22B	109.9
C3—C4—H4	120.8	C23—C22—H22B	109.9
C5—C4—H4	120.8	H22A—C22—H22B	108.3
C6—C5—C4	120.7 (4)	N4—C23—C22	109.8 (3)
C6—C5—H5	119.7	N4—C23—H23A	109.7
C4—C5—H5	119.7	C22—C23—H23A	109.7
C5—C6—C7	120.4 (4)	N4—C23—H23B	109.7
C5—C6—H6	119.8	C22—C23—H23B	109.7
C7—C6—H6	119.8	H23A—C23—H23B	108.2
C6—C7—C8	120.2 (5)	C25—C24—C29	118.2 (3)
C6—C7—H7	119.9	C25—C24—N5	118.9 (3)
C8—C7—H7	119.9	C29—C24—N5	122.9 (3)
C3—C8—C7	119.0 (4)	C26—C25—C24	120.9 (3)
C3—C8—H8	120.5	C26—C25—H25	119.5
C7—C8—H8	120.5	C24—C25—H25	119.5
C14—C9—C18'	113.4 (3)	C25—C26—C27	120.6 (3)
C14—C9—C18	112.7 (2)	C25—C26—H26	119.7
C18'—C9—C10'	108.8 (3)	C27—C26—H26	119.7
C18'—C9—C14'	110.4 (3)	C28—C27—C26	119.0 (3)
C10'—C9—C14'	104.2 (3)	C28—C27—H27	120.5
C14—C9—C10	108.7 (3)	C26—C27—H27	120.5
C18—C9—C10	105.9 (2)	C27—C28—C29	121.1 (3)
C14—C9—C2	112.6 (2)	C27—C28—H28	119.4
C18'—C9—C2	127.6 (3)	C29—C28—H28	119.4
C18—C9—C2	112.3 (2)	C28—C29—C24	120.2 (3)
C10'—C9—C2	102.9 (3)	C28—C29—H29	119.9
C14'—C9—C2	100.4 (3)	C24—C29—H29	119.9
C10—C9—C2	103.8 (2)	C11'—C10'—C9	111.7 (3)
C11—C10—C9	110.5 (2)	C11'—C10'—H10C	109.3
C11—C10—H10A	109.5	C9—C10'—H10C	109.3
C9—C10—H10A	109.5	C11'—C10'—H10D	109.3
C11—C10—H10B	109.5	C9—C10'—H10D	109.3
C9—C10—H10B	109.5	H10C—C10'—H10D	107.9
H10A—C10—H10B	108.1	C10'—C11'—C15'	109.6 (3)
C12—C11—C10	109.5 (3)	C10'—C11'—C12'	110.6 (3)
C12—C11—C15	109.1 (3)	C15'—C11'—C12'	109.1 (3)
C10—C11—C15	109.6 (3)	C10'—C11'—H11B	109.2
C12—C11—H11	109.5	C15'—C11'—H11B	109.2
C10—C11—H11	109.5	C12'—C11'—H11B	109.2
C15—C11—H11	109.5	C11'—C12'—C13'	108.0 (3)
C13—C12—C11	109.4 (2)	C11'—C12'—H12C	110.1
C13—C12—H12A	109.8	C13'—C12'—H12C	110.1
C11—C12—H12A	109.8	C11'—C12'—H12D	110.1
C13—C12—H12B	109.8	C13'—C12'—H12D	110.1
C11—C12—H12B	109.8	H12C—C12'—H12D	108.4
H12A—C12—H12B	108.2	C14'—C13'—C17'	108.8 (3)
C12—C13—C17	109.4 (3)	C14'—C13'—C12'	110.0 (3)
C12—C13—C14	109.9 (3)	C17'—C13'—C12'	109.2 (3)
C17—C13—C14	109.6 (3)	C14'—C13'—H13'	109.6
C12—C13—H13	109.3	C17'—C13'—H13'	109.6
C17—C13—H13	109.3	C12'—C13'—H13'	109.6
C14—C13—H13	109.3	C13'—C14'—C9	111.8 (3)
C9—C14—C13	109.1 (2)	C13'—C14'—H14C	109.3
C9—C14—H14A	109.9	C9—C14'—H14C	109.3
C13—C14—H14A	109.9	C13'—C14'—H14D	109.3
C9—C14—H14B	109.9	C9—C14'—H14D	109.3
C13—C14—H14B	109.9	H14C—C14'—H14D	107.9
H14A—C14—H14B	108.3	C16'—C15'—C11'	108.6 (3)
C11—C15—C16	108.8 (2)	C16'—C15'—H15C	110.0
C11—C15—H15A	109.9	C11'—C15'—H15C	110.0
C16—C15—H15A	109.9	C16'—C15'—H15D	110.0
C11—C15—H15B	109.9	C11'—C15'—H15D	110.0
C16—C15—H15B	109.9	H15C—C15'—H15D	108.3
H15A—C15—H15B	108.3	C18'—C16'—C15'	110.2 (3)
C17—C16—C15	109.9 (3)	C18'—C16'—C17'	109.5 (3)
C17—C16—C18	109.1 (3)	C15'—C16'—C17'	109.7 (3)
C15—C16—C18	109.5 (2)	C18'—C16'—H16'	109.1
C17—C16—H16	109.4	C15'—C16'—H16'	109.1
C15—C16—H16	109.4	C17'—C16'—H16'	109.1
C18—C16—H16	109.4	C16'—C17'—C13'	109.6 (3)
C13—C17—C16	110.0 (2)	C16'—C17'—H17C	109.7
C13—C17—H17A	109.7	C13'—C17'—H17C	109.7
C16—C17—H17A	109.7	C16'—C17'—H17D	109.7
C13—C17—H17B	109.7	C13'—C17'—H17D	109.7
C16—C17—H17B	109.7	H17C—C17'—H17D	108.2
H17A—C17—H17B	108.2	C9—C18'—C16'	110.3 (2)
C16—C18—C9	109.6 (2)	C9—C18'—H18C	109.6
C16—C18—H18A	109.7	C16'—C18'—H18C	109.6
C9—C18—H18A	109.7	C9—C18'—H18D	109.6
C16—C18—H18B	109.7	C16'—C18'—H18D	109.6
C9—C18—H18B	109.7	H18C—C18'—H18D	108.1
C2—N2—N3—C1	0.1 (3)	C18—C16—C17—C13	61.0 (3)
C2—N2—N3—C19	173.9 (3)	C17—C16—C18—C9	−57.2 (3)
N2—N3—C1—N1	0.1 (3)	C15—C16—C18—C9	63.1 (3)
C19—N3—C1—N1	−172.7 (3)	C14—C9—C18—C16	56.4 (3)
N2—N3—C1—S1	179.6 (2)	C10—C9—C18—C16	−62.4 (3)
C19—N3—C1—S1	6.8 (5)	C2—C9—C18—C16	−175.1 (3)
C2—N1—C1—N3	−0.2 (3)	C20—N4—C19—N3	−50.8 (4)
C3—N1—C1—N3	174.9 (3)	C23—N4—C19—N3	77.3 (4)
C2—N1—C1—S1	−179.7 (2)	C1—N3—C19—N4	−91.6 (4)
C3—N1—C1—S1	−4.6 (4)	N2—N3—C19—N4	95.9 (3)
N3—N2—C2—N1	−0.2 (3)	C19—N4—C20—C21	−172.1 (3)
N3—N2—C2—C9	179.8 (3)	C23—N4—C20—C21	57.8 (3)
C1—N1—C2—N2	0.2 (3)	C24—N5—C21—C20	−169.1 (3)
C3—N1—C2—N2	−174.3 (3)	C22—N5—C21—C20	57.3 (3)
C1—N1—C2—C9	−179.8 (3)	N4—C20—C21—N5	−56.3 (4)
C3—N1—C2—C9	5.7 (5)	C24—N5—C22—C23	168.3 (3)
C1—N1—C3—C4	91.4 (4)	C21—N5—C22—C23	−58.3 (3)
C2—N1—C3—C4	−94.7 (4)	C19—N4—C23—C22	171.3 (3)
C1—N1—C3—C8	−88.0 (4)	C20—N4—C23—C22	−59.5 (3)
C2—N1—C3—C8	85.9 (5)	N5—C22—C23—N4	59.2 (3)
C8—C3—C4—C5	−0.7 (6)	C21—N5—C24—C25	57.9 (4)
N1—C3—C4—C5	179.9 (4)	C22—N5—C24—C25	−170.7 (3)
C3—C4—C5—C6	0.0 (7)	C21—N5—C24—C29	−123.8 (3)
C4—C5—C6—C7	0.2 (8)	C22—N5—C24—C29	7.5 (4)
C5—C6—C7—C8	0.3 (8)	C29—C24—C25—C26	0.1 (5)
C4—C3—C8—C7	1.2 (7)	N5—C24—C25—C26	178.4 (3)
N1—C3—C8—C7	−179.4 (4)	C24—C25—C26—C27	0.1 (5)
C6—C7—C8—C3	−1.0 (7)	C25—C26—C27—C28	−0.5 (5)
N2—C2—C9—C14	−9.7 (4)	C26—C27—C28—C29	0.7 (5)
N1—C2—C9—C14	170.3 (3)	C27—C28—C29—C24	−0.6 (5)
N2—C2—C9—C18'	140.3 (4)	C25—C24—C29—C28	0.1 (4)
N1—C2—C9—C18'	−39.7 (5)	N5—C24—C29—C28	−178.1 (3)
N2—C2—C9—C18	−138.3 (3)	C18'—C9—C10'—C11'	57.1 (4)
N1—C2—C9—C18	41.8 (4)	C14'—C9—C10'—C11'	−60.7 (4)
N2—C2—C9—C10'	13.7 (4)	C2—C9—C10'—C11'	−165.1 (4)
N1—C2—C9—C10'	−166.2 (4)	C9—C10'—C11'—C15'	−58.3 (4)
N2—C2—C9—C14'	−93.6 (4)	C9—C10'—C11'—C12'	62.0 (4)
N1—C2—C9—C14'	86.5 (4)	C10'—C11'—C12'—C13'	−57.6 (4)
N2—C2—C9—C10	107.7 (3)	C15'—C11'—C12'—C13'	63.1 (4)
N1—C2—C9—C10	−72.2 (4)	C11'—C12'—C13'—C14'	57.6 (4)
C14—C9—C10—C11	−59.7 (3)	C11'—C12'—C13'—C17'	−61.8 (4)
C18—C9—C10—C11	61.7 (3)	C17'—C13'—C14'—C9	57.0 (4)
C2—C9—C10—C11	−179.8 (3)	C12'—C13'—C14'—C9	−62.6 (4)
C9—C10—C11—C12	58.5 (3)	C14—C9—C14'—C13'	56.1 (4)
C9—C10—C11—C15	−61.1 (3)	C18'—C9—C14'—C13'	−55.5 (4)
C10—C11—C12—C13	−58.4 (4)	C10'—C9—C14'—C13'	61.2 (4)
C15—C11—C12—C13	61.6 (3)	C2—C9—C14'—C13'	167.5 (4)
C11—C12—C13—C17	−60.0 (3)	C10'—C11'—C15'—C16'	59.0 (4)
C11—C12—C13—C14	60.3 (4)	C12'—C11'—C15'—C16'	−62.2 (4)
C18—C9—C14—C13	−56.6 (4)	C11'—C15'—C16'—C18'	−60.8 (4)
C10—C9—C14—C13	60.5 (3)	C11'—C15'—C16'—C17'	59.9 (4)
C2—C9—C14—C13	175.1 (3)	C18'—C16'—C17'—C13'	61.9 (4)
C12—C13—C14—C9	−61.8 (4)	C15'—C16'—C17'—C13'	−59.2 (4)
C17—C13—C14—C9	58.4 (4)	C14'—C13'—C17'—C16'	−60.0 (4)
C12—C11—C15—C16	−61.3 (3)	C12'—C13'—C17'—C16'	60.1 (4)
C10—C11—C15—C16	58.6 (3)	C10'—C9—C18'—C16'	−57.6 (4)
C11—C15—C16—C17	60.1 (3)	C14'—C9—C18'—C16'	56.1 (4)
C11—C15—C16—C18	−59.7 (3)	C2—C9—C18'—C16'	178.2 (3)
C12—C13—C17—C16	58.7 (3)	C15'—C16'—C18'—C9	61.0 (4)
C14—C13—C17—C16	−61.9 (3)	C17'—C16'—C18'—C9	−59.8 (4)
C15—C16—C17—C13	−59.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19B···S1i	0.99	2.84	3.593 (4)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19B⋯S1i	0.99	2.84	3.593 (4)	133

Symmetry code: (i) .