Ethyl 4-{[3-(adamantan-1-yl)-4-phenyl-5-sulfanyl-idene-4,5-dihydro-1H-1,2,4-triazol-1-yl]meth-yl}piperazine-1-carboxyl-ate.

The title mol-ecule, C(26)H(35)N(5)O(2)S, displays a chair-shaped piperazine ring, as well as a planar triazole ring whose phenyl substituent is perpendicular to the mean plane of the five-membered ring [dihedral angle = 90.00 (13)°]. The methyl-ene substituent on the piperazine ring occupies an equatorial site. Weak inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure. The crystal studied was a non-merohedral twin, with a 33.9 (3)% minor component.

Related literature

For the synthesis and application of the title compound, see: El-Emam & Ibrahim (1991 ▶). For the separation of non-morohedrally twinned diffraction data, see: Spek (2009 ▶).

Experimental

Crystal data

C26H35N5O2S

M = 481.65

Monoclinic,

a = 12.0469 (6) Å

b = 20.9213 (10) Å

c = 10.3249 (5) Å

β = 109.851 (6)°

V = 2447.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 100 K

0.30 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.952, T max = 0.984

17138 measured reflections

5655 independent reflections

4588 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.156

S = 1.11

5655 reflections

308 parameters

H-atom parameters constrained

Δρmax = 0.92 e Å−3

Δρmin = −0.40 e Å−3

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/S1600536811055668/xu5418sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055668/xu5418Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055668/xu5418Isup3.cml

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

C26H35N5O2S	F(000) = 1032
Mr = 481.65	Dx = 1.307 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5944 reflections
a = 12.0469 (6) Å	θ = 2.3–27.5°
b = 20.9213 (10) Å	µ = 0.17 mm−1
c = 10.3249 (5) Å	T = 100 K
β = 109.851 (6)°	Prism, colorless
V = 2447.6 (2) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	5655 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4588 reflections with I > 2σ(I)
Mirror	Rint = 0.046
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.3°
ω scan	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −27→27
Tmin = 0.952, Tmax = 0.984	l = −10→13
17138 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0559P)2 + 1.7988P] where P = (Fo2 + 2Fc2)/3
5655 reflections	(Δ/σ)max = 0.001
308 parameters	Δρmax = 0.92 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

	x	y	z	Uiso*/Ueq
S1	1.07961 (6)	0.35628 (3)	0.77520 (7)	0.02400 (17)
N2	1.06373 (17)	0.35443 (10)	0.3905 (2)	0.0199 (4)
N1	1.14387 (16)	0.41508 (9)	0.5741 (2)	0.0162 (4)
N3	1.03774 (17)	0.33163 (10)	0.5027 (2)	0.0191 (4)
N4	0.85438 (18)	0.27336 (10)	0.4214 (2)	0.0221 (5)
N5	0.61492 (19)	0.24428 (11)	0.3815 (3)	0.0304 (5)
O1	0.47688 (16)	0.25081 (9)	0.4818 (2)	0.0302 (4)
O2	0.50958 (18)	0.15641 (9)	0.3949 (2)	0.0334 (5)
C1	1.0859 (2)	0.36674 (11)	0.6181 (3)	0.0185 (5)
C2	1.12871 (19)	0.40508 (11)	0.4359 (2)	0.0161 (5)
C3	1.2096 (2)	0.46416 (11)	0.6668 (2)	0.0158 (5)
C4	1.1530 (2)	0.52024 (12)	0.6799 (3)	0.0197 (5)
H4	1.0716	0.5262	0.6288	0.024*
C5	1.2166 (2)	0.56774 (13)	0.7686 (3)	0.0243 (6)
H5	1.1790	0.6065	0.7784	0.029*
C6	1.3355 (2)	0.55824 (14)	0.8428 (3)	0.0263 (6)
H6	1.3796	0.5906	0.9029	0.032*
C7	1.3895 (2)	0.50143 (14)	0.8290 (3)	0.0265 (6)
H7	1.4707	0.4951	0.8803	0.032*
C8	1.3270 (2)	0.45372 (12)	0.7418 (2)	0.0197 (5)
H8	1.3642	0.4146	0.7337	0.024*
C9	1.18374 (19)	0.44264 (11)	0.3488 (2)	0.0157 (5)
C10	1.1833 (2)	0.51576 (12)	0.3709 (3)	0.0181 (5)
H10A	1.1011	0.5309	0.3492	0.022*
H10B	1.2273	0.5259	0.4686	0.022*
C11	1.2406 (2)	0.55027 (12)	0.2784 (3)	0.0190 (5)
H11	1.2398	0.5974	0.2943	0.023*
C12	1.1715 (2)	0.53586 (12)	0.1271 (3)	0.0226 (5)
H12A	1.2081	0.5583	0.0674	0.027*
H12B	1.0893	0.5512	0.1035	0.027*
C13	1.1723 (2)	0.46359 (13)	0.1033 (3)	0.0243 (6)
H13	1.1270	0.4539	0.0045	0.029*
C14	1.1149 (2)	0.42896 (13)	0.1953 (3)	0.0226 (5)
H14A	1.1140	0.3824	0.1782	0.027*
H14B	1.0322	0.4435	0.1723	0.027*
C15	1.3685 (2)	0.52770 (12)	0.3139 (3)	0.0211 (5)
H15A	1.4062	0.5504	0.2555	0.025*
H15B	1.4136	0.5376	0.4114	0.025*
C16	1.3704 (2)	0.45559 (12)	0.2898 (3)	0.0231 (5)
H16	1.4538	0.4408	0.3122	0.028*
C17	1.2999 (2)	0.44045 (13)	0.1382 (3)	0.0260 (6)
H17A	1.3369	0.4620	0.0777	0.031*
H17B	1.3008	0.3938	0.1224	0.031*
C18	1.3131 (2)	0.42047 (12)	0.3820 (3)	0.0209 (5)
H18A	1.3584	0.4293	0.4799	0.025*
H18B	1.3149	0.3738	0.3669	0.025*
C19	0.9811 (2)	0.26971 (11)	0.4941 (3)	0.0214 (5)
H19A	0.9957	0.2531	0.5882	0.026*
H19B	1.0165	0.2393	0.4457	0.026*
C20	0.8097 (2)	0.20785 (13)	0.3899 (3)	0.0288 (6)
H20A	0.8220	0.1840	0.4764	0.035*
H20B	0.8531	0.1856	0.3372	0.035*
C21	0.6788 (2)	0.21007 (15)	0.3057 (4)	0.0373 (7)
H21A	0.6671	0.2318	0.2169	0.045*
H21B	0.6476	0.1660	0.2859	0.045*
C22	0.6601 (2)	0.30815 (13)	0.4241 (3)	0.0260 (6)
H22A	0.6190	0.3268	0.4836	0.031*
H22B	0.6444	0.3358	0.3420	0.031*
C23	0.7922 (2)	0.30593 (12)	0.5025 (3)	0.0244 (6)
H23A	0.8229	0.3500	0.5237	0.029*
H23B	0.8070	0.2831	0.5908	0.029*
C24	0.5325 (2)	0.21268 (12)	0.4181 (3)	0.0244 (6)
C25	0.3970 (3)	0.21595 (15)	0.5362 (4)	0.0396 (8)
H25A	0.4430	0.1885	0.6141	0.047*
H25B	0.3439	0.1883	0.4637	0.047*
C26	0.3270 (3)	0.26259 (15)	0.5833 (3)	0.0378 (7)
H26A	0.2717	0.2398	0.6178	0.057*
H26B	0.2829	0.2901	0.5061	0.057*
H26C	0.3800	0.2889	0.6572	0.057*

	U11	U22	U33	U12	U13	U23
S1	0.0274 (3)	0.0241 (3)	0.0246 (3)	−0.0048 (2)	0.0142 (3)	0.0009 (3)
N2	0.0183 (10)	0.0185 (10)	0.0267 (11)	−0.0019 (8)	0.0124 (9)	−0.0006 (9)
N1	0.0144 (9)	0.0165 (10)	0.0198 (10)	−0.0024 (7)	0.0087 (8)	−0.0013 (8)
N3	0.0194 (10)	0.0172 (10)	0.0254 (11)	−0.0037 (8)	0.0136 (9)	−0.0013 (9)
N4	0.0216 (10)	0.0192 (10)	0.0295 (12)	−0.0051 (8)	0.0139 (9)	−0.0057 (9)
N5	0.0229 (11)	0.0304 (12)	0.0428 (14)	−0.0083 (9)	0.0178 (10)	−0.0138 (11)
O1	0.0272 (10)	0.0253 (10)	0.0445 (12)	−0.0067 (8)	0.0206 (9)	−0.0046 (9)
O2	0.0336 (11)	0.0199 (10)	0.0443 (12)	−0.0039 (8)	0.0100 (9)	−0.0032 (9)
C1	0.0135 (11)	0.0154 (11)	0.0288 (13)	0.0002 (8)	0.0101 (10)	−0.0001 (10)
C2	0.0130 (10)	0.0156 (11)	0.0208 (12)	0.0002 (8)	0.0074 (9)	−0.0009 (9)
C3	0.0151 (11)	0.0177 (11)	0.0159 (11)	−0.0037 (9)	0.0068 (9)	0.0011 (9)
C4	0.0171 (11)	0.0222 (13)	0.0204 (12)	−0.0007 (9)	0.0073 (10)	−0.0004 (10)
C5	0.0312 (14)	0.0222 (13)	0.0238 (13)	−0.0026 (10)	0.0150 (11)	−0.0035 (11)
C6	0.0275 (13)	0.0327 (15)	0.0201 (13)	−0.0164 (11)	0.0098 (11)	−0.0058 (11)
C7	0.0152 (11)	0.0454 (17)	0.0182 (12)	−0.0065 (11)	0.0049 (10)	0.0013 (12)
C8	0.0182 (11)	0.0257 (13)	0.0168 (12)	0.0018 (9)	0.0081 (10)	0.0047 (10)
C9	0.0139 (10)	0.0168 (11)	0.0179 (11)	−0.0017 (8)	0.0074 (9)	−0.0009 (9)
C10	0.0187 (11)	0.0180 (12)	0.0198 (12)	−0.0007 (9)	0.0094 (10)	−0.0009 (10)
C11	0.0218 (12)	0.0166 (11)	0.0209 (12)	−0.0002 (9)	0.0103 (10)	0.0021 (10)
C12	0.0214 (12)	0.0278 (13)	0.0200 (12)	0.0019 (10)	0.0089 (10)	0.0055 (11)
C13	0.0263 (13)	0.0317 (14)	0.0170 (12)	−0.0070 (11)	0.0100 (11)	−0.0046 (11)
C14	0.0210 (12)	0.0280 (13)	0.0214 (13)	−0.0078 (10)	0.0108 (11)	−0.0052 (11)
C15	0.0189 (11)	0.0236 (13)	0.0225 (12)	−0.0055 (9)	0.0094 (10)	0.0013 (10)
C16	0.0185 (11)	0.0245 (13)	0.0308 (14)	0.0035 (10)	0.0144 (11)	0.0066 (11)
C17	0.0328 (14)	0.0221 (13)	0.0325 (15)	−0.0021 (11)	0.0234 (12)	−0.0031 (11)
C18	0.0158 (11)	0.0223 (12)	0.0277 (13)	0.0033 (9)	0.0114 (10)	0.0068 (11)
C19	0.0221 (12)	0.0147 (12)	0.0301 (14)	−0.0041 (9)	0.0124 (11)	−0.0018 (10)
C20	0.0298 (14)	0.0217 (13)	0.0408 (16)	−0.0058 (10)	0.0199 (13)	−0.0115 (12)
C21	0.0288 (15)	0.0368 (17)	0.0490 (19)	−0.0089 (12)	0.0165 (14)	−0.0236 (15)
C22	0.0241 (13)	0.0228 (13)	0.0357 (15)	−0.0023 (10)	0.0164 (12)	−0.0019 (12)
C23	0.0241 (13)	0.0194 (13)	0.0339 (15)	−0.0052 (10)	0.0152 (12)	−0.0085 (11)
C24	0.0193 (12)	0.0219 (13)	0.0295 (14)	−0.0001 (10)	0.0051 (11)	0.0001 (11)
C25	0.0350 (16)	0.0367 (17)	0.053 (2)	−0.0081 (13)	0.0231 (15)	0.0045 (15)
C26	0.0297 (15)	0.0428 (18)	0.0458 (18)	0.0003 (13)	0.0192 (14)	0.0069 (15)

S1—C1	1.664 (3)	C11—H11	1.0000
N2—C2	1.306 (3)	C12—C13	1.532 (4)
N2—N3	1.384 (3)	C12—H12A	0.9900
N1—C2	1.392 (3)	C12—H12B	0.9900
N1—C1	1.390 (3)	C13—C14	1.533 (3)
N1—C3	1.443 (3)	C13—C17	1.534 (4)
N3—C1	1.351 (3)	C13—H13	1.0000
N3—C19	1.453 (3)	C14—H14A	0.9900
N4—C19	1.457 (3)	C14—H14B	0.9900
N4—C23	1.467 (3)	C15—C16	1.530 (3)
N4—C20	1.468 (3)	C15—H15A	0.9900
N5—C24	1.350 (3)	C15—H15B	0.9900
N5—C22	1.453 (3)	C16—C17	1.539 (4)
N5—C21	1.457 (4)	C16—C18	1.539 (3)
O1—C24	1.348 (3)	C16—H16	1.0000
O1—C25	1.463 (3)	C17—H17A	0.9900
O2—C24	1.214 (3)	C17—H17B	0.9900
C2—C9	1.507 (3)	C18—H18A	0.9900
C3—C8	1.380 (3)	C18—H18B	0.9900
C3—C4	1.386 (3)	C19—H19A	0.9900
C4—C5	1.392 (4)	C19—H19B	0.9900
C4—H4	0.9500	C20—C21	1.522 (4)
C5—C6	1.390 (4)	C20—H20A	0.9900
C5—H5	0.9500	C20—H20B	0.9900
C6—C7	1.385 (4)	C21—H21A	0.9900
C6—H6	0.9500	C21—H21B	0.9900
C7—C8	1.383 (4)	C22—C23	1.521 (3)
C7—H7	0.9500	C22—H22A	0.9900
C8—H8	0.9500	C22—H22B	0.9900
C9—C10	1.547 (3)	C23—H23A	0.9900
C9—C14	1.546 (3)	C23—H23B	0.9900
C9—C18	1.548 (3)	C25—C26	1.476 (4)
C10—C11	1.536 (3)	C25—H25A	0.9900
C10—H10A	0.9900	C25—H25B	0.9900
C10—H10B	0.9900	C26—H26A	0.9800
C11—C12	1.530 (3)	C26—H26B	0.9800
C11—C15	1.532 (3)	C26—H26C	0.9800
C2—N2—N3	104.9 (2)	C9—C14—H14B	109.6
C2—N1—C1	108.66 (19)	H14A—C14—H14B	108.1
C2—N1—C3	129.67 (19)	C16—C15—C11	109.51 (19)
C1—N1—C3	121.6 (2)	C16—C15—H15A	109.8
C1—N3—N2	113.53 (19)	C11—C15—H15A	109.8
C1—N3—C19	126.2 (2)	C16—C15—H15B	109.8
N2—N3—C19	119.4 (2)	C11—C15—H15B	109.8
C19—N4—C23	112.3 (2)	H15A—C15—H15B	108.2
C19—N4—C20	107.84 (19)	C15—C16—C17	109.6 (2)
C23—N4—C20	109.9 (2)	C15—C16—C18	109.6 (2)
C24—N5—C22	126.9 (2)	C17—C16—C18	108.8 (2)
C24—N5—C21	118.8 (2)	C15—C16—H16	109.6
C22—N5—C21	113.7 (2)	C17—C16—H16	109.6
C24—O1—C25	113.1 (2)	C18—C16—H16	109.6
N3—C1—N1	102.8 (2)	C13—C17—C16	109.7 (2)
N3—C1—S1	129.78 (19)	C13—C17—H17A	109.7
N1—C1—S1	127.46 (19)	C16—C17—H17A	109.7
N2—C2—N1	110.1 (2)	C13—C17—H17B	109.7
N2—C2—C9	122.7 (2)	C16—C17—H17B	109.7
N1—C2—C9	127.1 (2)	H17A—C17—H17B	108.2
C8—C3—C4	121.6 (2)	C16—C18—C9	110.43 (19)
C8—C3—N1	119.1 (2)	C16—C18—H18A	109.6
C4—C3—N1	119.3 (2)	C9—C18—H18A	109.6
C3—C4—C5	119.3 (2)	C16—C18—H18B	109.6
C3—C4—H4	120.4	C9—C18—H18B	109.6
C5—C4—H4	120.4	H18A—C18—H18B	108.1
C6—C5—C4	119.7 (2)	N3—C19—N4	111.9 (2)
C6—C5—H5	120.2	N3—C19—H19A	109.2
C4—C5—H5	120.2	N4—C19—H19A	109.2
C7—C6—C5	119.9 (2)	N3—C19—H19B	109.2
C7—C6—H6	120.1	N4—C19—H19B	109.2
C5—C6—H6	120.1	H19A—C19—H19B	107.9
C6—C7—C8	121.0 (2)	N4—C20—C21	109.2 (2)
C6—C7—H7	119.5	N4—C20—H20A	109.8
C8—C7—H7	119.5	C21—C20—H20A	109.8
C3—C8—C7	118.6 (2)	N4—C20—H20B	109.8
C3—C8—H8	120.7	C21—C20—H20B	109.8
C7—C8—H8	120.7	H20A—C20—H20B	108.3
C2—C9—C10	113.77 (19)	N5—C21—C20	110.0 (2)
C2—C9—C14	108.89 (19)	N5—C21—H21A	109.7
C10—C9—C14	107.90 (19)	C20—C21—H21A	109.7
C2—C9—C18	108.98 (19)	N5—C21—H21B	109.7
C10—C9—C18	108.48 (19)	C20—C21—H21B	109.7
C14—C9—C18	108.7 (2)	H21A—C21—H21B	108.2
C11—C10—C9	110.37 (19)	N5—C22—C23	110.5 (2)
C11—C10—H10A	109.6	N5—C22—H22A	109.6
C9—C10—H10A	109.6	C23—C22—H22A	109.6
C11—C10—H10B	109.6	N5—C22—H22B	109.6
C9—C10—H10B	109.6	C23—C22—H22B	109.6
H10A—C10—H10B	108.1	H22A—C22—H22B	108.1
C12—C11—C15	109.8 (2)	N4—C23—C22	110.8 (2)
C12—C11—C10	109.8 (2)	N4—C23—H23A	109.5
C15—C11—C10	109.5 (2)	C22—C23—H23A	109.5
C12—C11—H11	109.2	N4—C23—H23B	109.5
C15—C11—H11	109.2	C22—C23—H23B	109.5
C10—C11—H11	109.2	H23A—C23—H23B	108.1
C11—C12—C13	109.1 (2)	O2—C24—O1	123.5 (2)
C11—C12—H12A	109.9	O2—C24—N5	124.0 (3)
C13—C12—H12A	109.9	O1—C24—N5	112.4 (2)
C11—C12—H12B	109.9	O1—C25—C26	108.7 (2)
C13—C12—H12B	109.9	O1—C25—H25A	109.9
H12A—C12—H12B	108.3	C26—C25—H25A	109.9
C14—C13—C12	109.8 (2)	O1—C25—H25B	109.9
C14—C13—C17	109.4 (2)	C26—C25—H25B	109.9
C12—C13—C17	109.5 (2)	H25A—C25—H25B	108.3
C14—C13—H13	109.4	C25—C26—H26A	109.5
C12—C13—H13	109.4	C25—C26—H26B	109.5
C17—C13—H13	109.4	H26A—C26—H26B	109.5
C13—C14—C9	110.48 (19)	C25—C26—H26C	109.5
C13—C14—H14A	109.6	H26A—C26—H26C	109.5
C9—C14—H14A	109.6	H26B—C26—H26C	109.5
C13—C14—H14B	109.6
C2—N2—N3—C1	−0.4 (3)	C11—C12—C13—C14	59.8 (3)
C2—N2—N3—C19	−170.7 (2)	C11—C12—C13—C17	−60.3 (3)
N2—N3—C1—N1	1.0 (3)	C12—C13—C14—C9	−60.4 (3)
C19—N3—C1—N1	170.5 (2)	C17—C13—C14—C9	59.8 (3)
N2—N3—C1—S1	−178.88 (18)	C2—C9—C14—C13	−177.0 (2)
C19—N3—C1—S1	−9.4 (4)	C10—C9—C14—C13	59.1 (3)
C2—N1—C1—N3	−1.2 (2)	C18—C9—C14—C13	−58.4 (3)
C3—N1—C1—N3	−179.45 (19)	C12—C11—C15—C16	−60.3 (3)
C2—N1—C1—S1	178.72 (18)	C10—C11—C15—C16	60.4 (3)
C3—N1—C1—S1	0.5 (3)	C11—C15—C16—C17	59.3 (3)
N3—N2—C2—N1	−0.4 (2)	C11—C15—C16—C18	−60.1 (3)
N3—N2—C2—C9	175.8 (2)	C14—C13—C17—C16	−60.6 (3)
C1—N1—C2—N2	1.0 (3)	C12—C13—C17—C16	59.7 (3)
C3—N1—C2—N2	179.1 (2)	C15—C16—C17—C13	−59.2 (3)
C1—N1—C2—C9	−175.0 (2)	C18—C16—C17—C13	60.6 (3)
C3—N1—C2—C9	3.1 (4)	C15—C16—C18—C9	59.7 (3)
C2—N1—C3—C8	−89.4 (3)	C17—C16—C18—C9	−60.1 (3)
C1—N1—C3—C8	88.4 (3)	C2—C9—C18—C16	177.3 (2)
C2—N1—C3—C4	91.4 (3)	C10—C9—C18—C16	−58.3 (3)
C1—N1—C3—C4	−90.7 (3)	C14—C9—C18—C16	58.8 (3)
C8—C3—C4—C5	1.3 (4)	C1—N3—C19—N4	110.8 (3)
N1—C3—C4—C5	−179.6 (2)	N2—N3—C19—N4	−80.2 (3)
C3—C4—C5—C6	−0.2 (4)	C23—N4—C19—N3	−71.6 (3)
C4—C5—C6—C7	−0.6 (4)	C20—N4—C19—N3	167.1 (2)
C5—C6—C7—C8	0.2 (4)	C19—N4—C20—C21	−176.4 (2)
C4—C3—C8—C7	−1.7 (4)	C23—N4—C20—C21	60.9 (3)
N1—C3—C8—C7	179.2 (2)	C24—N5—C21—C20	−117.4 (3)
C6—C7—C8—C3	0.9 (4)	C22—N5—C21—C20	55.1 (3)
N2—C2—C9—C10	141.9 (2)	N4—C20—C21—N5	−58.0 (3)
N1—C2—C9—C10	−42.6 (3)	C24—N5—C22—C23	118.9 (3)
N2—C2—C9—C14	21.5 (3)	C21—N5—C22—C23	−52.9 (3)
N1—C2—C9—C14	−163.0 (2)	C19—N4—C23—C22	−179.4 (2)
N2—C2—C9—C18	−96.9 (3)	C20—N4—C23—C22	−59.3 (3)
N1—C2—C9—C18	78.6 (3)	N5—C22—C23—N4	54.2 (3)
C2—C9—C10—C11	−179.92 (19)	C25—O1—C24—O2	7.5 (4)
C14—C9—C10—C11	−59.0 (2)	C25—O1—C24—N5	−173.4 (2)
C18—C9—C10—C11	58.6 (2)	C22—N5—C24—O2	−169.5 (3)
C9—C10—C11—C12	60.4 (2)	C21—N5—C24—O2	1.9 (4)
C9—C10—C11—C15	−60.2 (3)	C22—N5—C24—O1	11.4 (4)
C15—C11—C12—C13	60.6 (3)	C21—N5—C24—O1	−177.2 (2)
C10—C11—C12—C13	−59.9 (3)	C24—O1—C25—C26	−171.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.95	2.48	3.406 (3)	166
C8—H8···O2ii	0.95	2.46	3.207 (3)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.95	2.48	3.406 (3)	166
C8—H8⋯O2ii	0.95	2.46	3.207 (3)	135

Symmetry codes: (i) ; (ii) .