1-Benzoyl-3-[3-cyano-8-methyl-4-(1-methyl-1H-pyrrol-2-yl)-5,6,7,8-tetra-hydro-quinolin-2-yl]thio-urea.

In the N-substituted benzoyl-thio-urea, C(24)H(23)N(5)OS, the benzoyl-thio-urea unit is non-planar (r.m.s. deviation = 0.126 Å). The aliphatic part of the tetra-hydro-quinoline fused-ring system is disordered over two positions in a 0.592 (5):0.408 (5) ratio. The pyridine and pyrrole rings are twisted by 55.2 (1)° in order to avoid crowding of their respective substituents. Pairs of mol-ecules are linked by N-H⋯N hydrogen bonds, forming centrosymmetric dimers. Furthermore, an intra-molecular N-H⋯O hydrogen bond stabilizes the mol-ecular conformation.

Related literature

For medicinal properties of cyano­pyridines, see: Cocco et al. (2005 ▶); El-Hawash et al. (2006 ▶).

Experimental

Crystal data

C24H23N5OS

M = 429.53

Triclinic,

a = 9.7072 (4) Å

b = 10.4928 (5) Å

c = 11.8828 (5) Å

α = 82.245 (4)°

β = 84.263 (3)°

γ = 63.671 (4)°

V = 1073.76 (8) Å3

Z = 2

Cu Kα radiation

μ = 1.55 mm−1

T = 100 K

0.30 × 0.20 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.654, T max = 0.747

7386 measured reflections

4218 independent reflections

3897 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.146

S = 1.03

4218 reflections

294 parameters

20 restraints

H-atom parameters constrained

Δρmax = 1.25 e Å−3

Δρmin = −0.46 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/S1600536811033046/bt5613sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033046/bt5613Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033046/bt5613Isup3.cml

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

C24H23N5OS	Z = 2
Mr = 429.53	F(000) = 452
Triclinic, P1	Dx = 1.329 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 9.7072 (4) Å	Cell parameters from 4274 reflections
b = 10.4928 (5) Å	θ = 3.8–74.2°
c = 11.8828 (5) Å	µ = 1.55 mm−1
α = 82.245 (4)°	T = 100 K
β = 84.263 (3)°	Prism, brown–orange
γ = 63.671 (4)°	0.30 × 0.20 × 0.20 mm
V = 1073.76 (8) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	4218 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3897 reflections with I > 2σ(I)
Mirror	Rint = 0.020
Detector resolution: 10.4041 pixels mm-1	θmax = 74.3°, θmin = 3.8°
ω scans	h = −11→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→13
Tmin = 0.654, Tmax = 0.747	l = −14→14
7386 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) = 0.146	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0825P)2 + 0.7756P] where P = (Fo2 + 2Fc2)/3
4218 reflections	(Δ/σ)max = 0.001
294 parameters	Δρmax = 1.25 e Å−3
20 restraints	Δρmin = −0.46 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.25749 (6)	0.66030 (6)	0.41290 (5)	0.03749 (18)
O1	0.63636 (17)	0.62389 (15)	0.14578 (12)	0.0305 (3)
N1	0.2933 (2)	1.01329 (17)	0.24918 (14)	0.0344 (4)
N2	0.16227 (18)	1.03258 (17)	0.67653 (13)	0.0251 (3)
N3	0.49398 (19)	0.73393 (17)	0.59776 (13)	0.0270 (4)
N4	0.43635 (19)	0.77111 (16)	0.29593 (13)	0.0240 (3)
H4	0.5199	0.7558	0.2524	0.029*
N5	0.48814 (18)	0.54112 (16)	0.26536 (13)	0.0235 (3)
H5	0.4773	0.4630	0.2898	0.028*
C1	0.2196 (5)	1.2331 (4)	0.0699 (3)	0.0388 (8)	0.592 (5)
H1A	0.1607	1.3010	0.0078	0.058*	0.592 (5)
H1B	0.2515	1.1353	0.0516	0.058*	0.592 (5)
H1C	0.3109	1.2470	0.0796	0.058*	0.592 (5)
C2	0.1198 (4)	1.2577 (3)	0.1793 (3)	0.0238 (7)	0.592 (5)
H2	0.0328	1.2349	0.1681	0.029*	0.592 (5)
C3	0.0504 (4)	1.4093 (4)	0.2080 (4)	0.0286 (11)	0.592 (5)
H3A	−0.0277	1.4696	0.1520	0.034*	0.592 (5)
H3B	0.1320	1.4426	0.1998	0.034*	0.592 (5)
C4	−0.0245 (11)	1.4323 (12)	0.3259 (5)	0.0466 (10)	0.592 (5)
H4A	−0.1133	1.4088	0.3331	0.056*	0.592 (5)
H4B	−0.0628	1.5339	0.3389	0.056*	0.592 (5)
C1'	0.1144 (7)	1.2261 (6)	0.0836 (4)	0.0388 (8)	0.408
H1'A	0.0981	1.2943	0.0155	0.058*	0.408 (5)
H1'B	0.0150	1.2317	0.1156	0.058*	0.408 (5)
H1'C	0.1799	1.1291	0.0633	0.058*	0.408 (5)
C2'	0.1916 (6)	1.2618 (5)	0.1706 (4)	0.0238 (7)	0.408
H2'	0.2952	1.2502	0.1384	0.029*	0.408 (5)
C3'	0.1035 (7)	1.4112 (6)	0.2064 (5)	0.0286 (11)	0.408
H3'1	0.1780	1.4469	0.2214	0.034*	0.408 (5)
H3'2	0.0414	1.4746	0.1426	0.034*	0.408 (5)
C4'	−0.0017 (15)	1.4211 (19)	0.3106 (6)	0.0466 (10)	0.408
H4'1	−0.0741	1.3818	0.2978	0.056*	0.408 (5)
H4'2	−0.0628	1.5225	0.3244	0.056*	0.408 (5)
C5	0.0917 (2)	1.3376 (2)	0.41467 (16)	0.0295 (4)
H5A	0.1619	1.3809	0.4228	0.035*	0.592 (5)
H5B	0.0354	1.3367	0.4888	0.035*	0.592 (5)
H5C	0.1599	1.3801	0.4302	0.035*	0.408 (5)
H5D	0.0233	1.3403	0.4829	0.035*	0.408 (5)
C6	0.1874 (2)	1.18481 (19)	0.38818 (16)	0.0255 (4)
C7	0.2144 (3)	1.1494 (2)	0.27625 (16)	0.0357 (5)
C8	0.2487 (2)	1.07401 (19)	0.47547 (15)	0.0217 (4)
C9	0.3370 (2)	0.93424 (19)	0.44573 (15)	0.0223 (4)
C10	0.3513 (2)	0.90956 (19)	0.33176 (16)	0.0249 (4)
C11	0.2239 (2)	1.10237 (18)	0.59522 (15)	0.0220 (4)
C12	0.2572 (2)	1.1937 (2)	0.64847 (16)	0.0253 (4)
H12	0.3007	1.2552	0.6133	0.030*
C13	0.2148 (2)	1.1790 (2)	0.76492 (16)	0.0298 (4)
H13	0.2259	1.2276	0.8228	0.036*
C14	0.1548 (2)	1.0819 (2)	0.77873 (16)	0.0291 (4)
H14	0.1143	1.0532	0.8484	0.035*
C15	0.0892 (2)	0.9433 (2)	0.65744 (19)	0.0334 (5)
H15A	0.1105	0.8670	0.7200	0.050*
H15B	0.1301	0.9011	0.5856	0.050*
H15C	−0.0221	1.0016	0.6538	0.050*
C16	0.4215 (2)	0.82116 (19)	0.53048 (15)	0.0225 (4)
C17	0.3993 (2)	0.66125 (19)	0.32327 (16)	0.0244 (4)
C18	0.5910 (2)	0.53169 (19)	0.17416 (15)	0.0233 (4)
C19	0.6415 (2)	0.40659 (19)	0.10662 (15)	0.0244 (4)
C20	0.7465 (3)	0.4002 (2)	0.01627 (18)	0.0352 (5)
H20	0.7870	0.4686	0.0045	0.042*
C21	0.7924 (3)	0.2941 (2)	−0.05700 (19)	0.0416 (6)
H21	0.8637	0.2905	−0.1189	0.050*
C22	0.7342 (3)	0.1942 (2)	−0.03949 (18)	0.0371 (5)
H22	0.7655	0.1217	−0.0893	0.045*
C23	0.6301 (3)	0.1997 (2)	0.05058 (18)	0.0334 (5)
H23	0.5905	0.1306	0.0625	0.040*
C24	0.5832 (2)	0.3061 (2)	0.12401 (16)	0.0281 (4)
H24	0.5116	0.3097	0.1856	0.034*

	U11	U22	U33	U12	U13	U23
S1	0.0378 (3)	0.0290 (3)	0.0459 (3)	−0.0144 (2)	0.0180 (2)	−0.0197 (2)
O1	0.0407 (8)	0.0228 (7)	0.0261 (7)	−0.0125 (6)	0.0078 (6)	−0.0084 (5)
N1	0.0571 (11)	0.0163 (8)	0.0187 (8)	−0.0045 (8)	−0.0059 (7)	−0.0047 (6)
N2	0.0255 (8)	0.0218 (8)	0.0216 (8)	−0.0050 (6)	0.0024 (6)	−0.0033 (6)
N3	0.0295 (8)	0.0211 (8)	0.0220 (8)	−0.0038 (7)	0.0016 (6)	−0.0031 (6)
N4	0.0301 (8)	0.0163 (7)	0.0192 (7)	−0.0036 (6)	0.0019 (6)	−0.0063 (6)
N5	0.0296 (8)	0.0146 (7)	0.0213 (8)	−0.0047 (6)	0.0022 (6)	−0.0057 (6)
C1	0.055 (2)	0.0305 (15)	0.0249 (14)	−0.0156 (15)	−0.0034 (14)	0.0055 (11)
C2	0.028 (2)	0.0185 (11)	0.0216 (12)	−0.0078 (15)	−0.0025 (14)	−0.0007 (9)
C3	0.027 (3)	0.0208 (11)	0.0229 (11)	0.0015 (16)	0.0031 (17)	0.0022 (8)
C4	0.057 (3)	0.026 (2)	0.0306 (18)	0.0067 (18)	−0.0013 (17)	−0.0077 (17)
C1'	0.055 (2)	0.0305 (15)	0.0249 (14)	−0.0156 (15)	−0.0034 (14)	0.0055 (11)
C2'	0.028 (2)	0.0185 (11)	0.0216 (12)	−0.0078 (15)	−0.0025 (14)	−0.0007 (9)
C3'	0.027 (3)	0.0208 (11)	0.0229 (11)	0.0015 (16)	0.0031 (17)	0.0022 (8)
C4'	0.057 (3)	0.026 (2)	0.0306 (18)	0.0067 (18)	−0.0013 (17)	−0.0077 (17)
C5	0.0386 (11)	0.0161 (9)	0.0231 (9)	−0.0013 (8)	−0.0022 (8)	−0.0050 (7)
C6	0.0326 (10)	0.0163 (9)	0.0215 (9)	−0.0041 (7)	−0.0028 (7)	−0.0050 (7)
C7	0.0585 (14)	0.0157 (9)	0.0199 (9)	−0.0030 (9)	−0.0064 (9)	−0.0036 (7)
C8	0.0233 (8)	0.0188 (9)	0.0193 (9)	−0.0050 (7)	−0.0004 (7)	−0.0049 (7)
C9	0.0247 (9)	0.0173 (9)	0.0196 (9)	−0.0042 (7)	−0.0002 (7)	−0.0032 (7)
C10	0.0317 (10)	0.0166 (9)	0.0212 (9)	−0.0047 (7)	−0.0009 (7)	−0.0056 (7)
C11	0.0225 (8)	0.0165 (8)	0.0189 (8)	−0.0014 (7)	0.0013 (6)	−0.0030 (6)
C12	0.0300 (9)	0.0189 (9)	0.0208 (9)	−0.0045 (7)	0.0022 (7)	−0.0068 (7)
C13	0.0363 (10)	0.0239 (10)	0.0196 (9)	−0.0034 (8)	0.0000 (7)	−0.0073 (7)
C14	0.0314 (10)	0.0279 (10)	0.0172 (9)	−0.0038 (8)	0.0042 (7)	−0.0036 (7)
C15	0.0312 (10)	0.0335 (11)	0.0349 (11)	−0.0145 (9)	0.0041 (8)	−0.0043 (9)
C16	0.0246 (9)	0.0182 (9)	0.0193 (8)	−0.0043 (7)	0.0048 (7)	−0.0070 (7)
C17	0.0282 (9)	0.0169 (9)	0.0214 (9)	−0.0029 (7)	−0.0008 (7)	−0.0059 (7)
C18	0.0274 (9)	0.0168 (8)	0.0191 (8)	−0.0030 (7)	−0.0018 (7)	−0.0043 (7)
C19	0.0284 (9)	0.0167 (9)	0.0199 (9)	−0.0011 (7)	−0.0031 (7)	−0.0049 (7)
C20	0.0436 (12)	0.0252 (10)	0.0298 (10)	−0.0087 (9)	0.0092 (9)	−0.0109 (8)
C21	0.0521 (14)	0.0286 (11)	0.0304 (11)	−0.0050 (10)	0.0106 (10)	−0.0129 (9)
C22	0.0472 (12)	0.0226 (10)	0.0279 (10)	0.0007 (9)	−0.0066 (9)	−0.0125 (8)
C23	0.0417 (11)	0.0218 (10)	0.0322 (11)	−0.0062 (9)	−0.0093 (9)	−0.0096 (8)
C24	0.0344 (10)	0.0222 (9)	0.0230 (9)	−0.0064 (8)	−0.0041 (8)	−0.0065 (7)

S1—C17	1.657 (2)	C3'—H3'2	0.9900
O1—C18	1.226 (2)	C4'—C5	1.532 (9)
N1—C10	1.320 (2)	C4'—H4'1	0.9900
N1—C7	1.354 (2)	C4'—H4'2	0.9900
N2—C14	1.366 (3)	C5—C6	1.513 (2)
N2—C11	1.382 (2)	C5—H5A	0.9900
N2—C15	1.452 (3)	C5—H5B	0.9900
N3—C16	1.147 (2)	C5—H5C	0.9900
N4—C17	1.344 (3)	C5—H5D	0.9900
N4—C10	1.416 (2)	C6—C7	1.398 (3)
N4—H4	0.8800	C6—C8	1.402 (3)
N5—C18	1.380 (2)	C8—C9	1.405 (2)
N5—C17	1.399 (2)	C8—C11	1.468 (2)
N5—H5	0.8800	C9—C10	1.395 (3)
C1—C2	1.521 (4)	C9—C16	1.440 (2)
C1—H1A	0.9800	C11—C12	1.379 (3)
C1—H1B	0.9800	C12—C13	1.412 (3)
C1—H1C	0.9800	C12—H12	0.9500
C2—C3	1.500 (5)	C13—C14	1.366 (3)
C2—C7	1.547 (3)	C13—H13	0.9500
C2—H2	1.0000	C14—H14	0.9500
C3—C4	1.511 (6)	C15—H15A	0.9800
C3—H3A	0.9900	C15—H15B	0.9800
C3—H3B	0.9900	C15—H15C	0.9800
C4—C5	1.527 (7)	C18—C19	1.497 (2)
C4—H4A	0.9900	C19—C24	1.386 (3)
C4—H4B	0.9900	C19—C20	1.391 (3)
C1'—C2'	1.510 (6)	C20—C21	1.393 (3)
C1'—H1'A	0.9800	C20—H20	0.9500
C1'—H1'B	0.9800	C21—C22	1.380 (4)
C1'—H1'C	0.9800	C21—H21	0.9500
C2'—C3'	1.513 (6)	C22—C23	1.385 (3)
C2'—C7	1.563 (5)	C22—H22	0.9500
C2'—H2'	1.0000	C23—C24	1.396 (3)
C3'—C4'	1.508 (9)	C23—H23	0.9500
C3'—H3'1	0.9900	C24—H24	0.9500
C10—N1—C7	118.70 (16)	C6—C5—H5C	109.8
C14—N2—C11	108.27 (16)	C4—C5—H5C	111.7
C14—N2—C15	123.49 (17)	C4'—C5—H5C	109.7
C11—N2—C15	127.26 (17)	C6—C5—H5D	110.1
C17—N4—C10	125.08 (16)	C4—C5—H5D	101.5
C17—N4—H4	117.5	C4'—C5—H5D	111.1
C10—N4—H4	117.5	H5C—C5—H5D	108.3
C18—N5—C17	127.16 (16)	C7—C6—C8	117.99 (17)
C18—N5—H5	116.4	C7—C6—C5	121.05 (17)
C17—N5—H5	116.4	C8—C6—C5	120.94 (16)
C2—C1—H1A	109.5	N1—C7—C6	122.96 (17)
C2—C1—H1B	109.5	N1—C7—C2	114.67 (19)
H1A—C1—H1B	109.5	C6—C7—C2	120.51 (19)
C2—C1—H1C	109.5	N1—C7—C2'	112.4 (2)
H1A—C1—H1C	109.5	C6—C7—C2'	123.2 (2)
H1B—C1—H1C	109.5	C6—C8—C9	118.42 (16)
C3—C2—C1	113.7 (3)	C6—C8—C11	121.25 (16)
C3—C2—C7	112.8 (3)	C9—C8—C11	120.33 (16)
C1—C2—C7	108.8 (3)	C10—C9—C8	118.92 (16)
C3—C2—H2	107.1	C10—C9—C16	120.70 (16)
C1—C2—H2	107.1	C8—C9—C16	120.18 (16)
C7—C2—H2	107.1	N1—C10—C9	122.84 (17)
C2—C3—C4	115.0 (5)	N1—C10—N4	115.13 (16)
C2—C3—H3A	108.5	C9—C10—N4	121.96 (16)
C4—C3—H3A	108.5	C12—C11—N2	107.94 (16)
C2—C3—H3B	108.5	C12—C11—C8	129.53 (17)
C4—C3—H3B	108.5	N2—C11—C8	122.51 (17)
H3A—C3—H3B	107.5	C11—C12—C13	107.41 (18)
C3—C4—C5	110.0 (5)	C11—C12—H12	126.3
C3—C4—H4A	109.7	C13—C12—H12	126.3
C5—C4—H4A	109.7	C14—C13—C12	107.14 (17)
C3—C4—H4B	109.7	C14—C13—H13	126.4
C5—C4—H4B	109.7	C12—C13—H13	126.4
H4A—C4—H4B	108.2	N2—C14—C13	109.21 (17)
C2'—C1'—H1'A	109.5	N2—C14—H14	125.4
C2'—C1'—H1'B	109.5	C13—C14—H14	125.4
H1'A—C1'—H1'B	109.5	N2—C15—H15A	109.5
C2'—C1'—H1'C	109.5	N2—C15—H15B	109.5
H1'A—C1'—H1'C	109.5	H15A—C15—H15B	109.5
H1'B—C1'—H1'C	109.5	N2—C15—H15C	109.5
C1'—C2'—C3'	114.5 (4)	H15A—C15—H15C	109.5
C1'—C2'—C7	106.8 (4)	H15B—C15—H15C	109.5
C3'—C2'—C7	109.8 (4)	N3—C16—C9	176.5 (2)
C1'—C2'—H2'	108.5	N4—C17—N5	114.65 (16)
C3'—C2'—H2'	108.5	N4—C17—S1	125.98 (14)
C7—C2'—H2'	108.5	N5—C17—S1	119.31 (14)
C4'—C3'—C2'	114.1 (8)	O1—C18—N5	122.12 (16)
C4'—C3'—H3'1	108.7	O1—C18—C19	120.29 (17)
C2'—C3'—H3'1	108.7	N5—C18—C19	117.55 (16)
C4'—C3'—H3'2	108.7	C24—C19—C20	119.68 (18)
C2'—C3'—H3'2	108.7	C24—C19—C18	124.42 (17)
H3'1—C3'—H3'2	107.6	C20—C19—C18	115.74 (18)
C3'—C4'—C5	110.5 (8)	C19—C20—C21	120.4 (2)
C3'—C4'—H4'1	109.6	C19—C20—H20	119.8
C5—C4'—H4'1	109.6	C21—C20—H20	119.8
C3'—C4'—H4'2	109.6	C22—C21—C20	119.8 (2)
C5—C4'—H4'2	109.6	C22—C21—H21	120.1
H4'1—C4'—H4'2	108.1	C20—C21—H21	120.1
C6—C5—C4	114.9 (4)	C21—C22—C23	120.07 (19)
C6—C5—C4'	107.8 (6)	C21—C22—H22	120.0
C4—C5—C4'	10.0 (5)	C23—C22—H22	120.0
C6—C5—H5A	108.5	C22—C23—C24	120.4 (2)
C4—C5—H5A	108.5	C22—C23—H23	119.8
C4'—C5—H5A	105.9	C24—C23—H23	119.8
C6—C5—H5B	108.5	C19—C24—C23	119.7 (2)
C4—C5—H5B	108.5	C19—C24—H24	120.2
C4'—C5—H5B	118.2	C23—C24—H24	120.2
H5A—C5—H5B	107.5
C1—C2—C3—C4	−169.1 (6)	C7—N1—C10—C9	−1.1 (3)
C7—C2—C3—C4	−44.7 (7)	C7—N1—C10—N4	−178.1 (2)
C2—C3—C4—C5	56.7 (12)	C8—C9—C10—N1	4.3 (3)
C1'—C2'—C3'—C4'	92.8 (9)	C16—C9—C10—N1	−170.5 (2)
C7—C2'—C3'—C4'	−27.3 (9)	C8—C9—C10—N4	−178.92 (18)
C2'—C3'—C4'—C5	64.7 (16)	C16—C9—C10—N4	6.2 (3)
C3—C4—C5—C6	−45.1 (12)	C17—N4—C10—N1	−117.5 (2)
C3—C4—C5—C4'	0(8)	C17—N4—C10—C9	65.6 (3)
C3'—C4'—C5—C6	−57.1 (15)	C14—N2—C11—C12	1.0 (2)
C3'—C4'—C5—C4	166 (10)	C15—N2—C11—C12	169.90 (18)
C4—C5—C6—C7	25.2 (6)	C14—N2—C11—C8	179.69 (16)
C4'—C5—C6—C7	17.8 (8)	C15—N2—C11—C8	−11.5 (3)
C4—C5—C6—C8	−153.3 (6)	C6—C8—C11—C12	−56.1 (3)
C4'—C5—C6—C8	−160.7 (8)	C9—C8—C11—C12	123.0 (2)
C10—N1—C7—C6	−2.0 (4)	C6—C8—C11—N2	125.6 (2)
C10—N1—C7—C2	−166.5 (2)	C9—C8—C11—N2	−55.3 (3)
C10—N1—C7—C2'	164.6 (3)	N2—C11—C12—C13	0.0 (2)
C8—C6—C7—N1	1.6 (4)	C8—C11—C12—C13	−178.49 (18)
C5—C6—C7—N1	−176.9 (2)	C11—C12—C13—C14	−1.1 (2)
C8—C6—C7—C2	165.3 (2)	C11—N2—C14—C13	−1.8 (2)
C5—C6—C7—C2	−13.2 (4)	C15—N2—C14—C13	−171.12 (18)
C8—C6—C7—C2'	−163.5 (3)	C12—C13—C14—N2	1.7 (2)
C5—C6—C7—C2'	17.9 (4)	C10—C9—C16—N3	100 (3)
C3—C2—C7—N1	−172.9 (3)	C8—C9—C16—N3	−75 (3)
C1—C2—C7—N1	−45.7 (4)	C10—N4—C17—N5	171.52 (17)
C3—C2—C7—C6	22.2 (4)	C10—N4—C17—S1	−5.9 (3)
C1—C2—C7—C6	149.3 (3)	C18—N5—C17—N4	−10.1 (3)
C3—C2—C7—C2'	−81.8 (5)	C18—N5—C17—S1	167.55 (15)
C1—C2—C7—C2'	45.4 (5)	C17—N5—C18—O1	13.3 (3)
C1'—C2'—C7—N1	55.5 (4)	C17—N5—C18—C19	−164.14 (17)
C3'—C2'—C7—N1	−179.8 (4)	O1—C18—C19—C24	−172.29 (18)
C1'—C2'—C7—C6	−138.0 (4)	N5—C18—C19—C24	5.2 (3)
C3'—C2'—C7—C6	−13.2 (5)	O1—C18—C19—C20	3.2 (3)
C1'—C2'—C7—C2	−45.2 (5)	N5—C18—C19—C20	−179.29 (17)
C3'—C2'—C7—C2	79.6 (6)	C24—C19—C20—C21	0.4 (3)
C7—C6—C8—C9	1.6 (3)	C18—C19—C20—C21	−175.3 (2)
C5—C6—C8—C9	−179.84 (18)	C19—C20—C21—C22	−0.4 (4)
C7—C6—C8—C11	−179.3 (2)	C20—C21—C22—C23	0.1 (3)
C5—C6—C8—C11	−0.7 (3)	C21—C22—C23—C24	0.2 (3)
C6—C8—C9—C10	−4.4 (3)	C20—C19—C24—C23	−0.1 (3)
C11—C8—C9—C10	176.45 (18)	C18—C19—C24—C23	175.20 (18)
C6—C8—C9—C16	170.46 (18)	C22—C23—C24—C19	−0.2 (3)
C11—C8—C9—C16	−8.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1	0.88	1.90	2.594 (2)	135
N5—H5···N3i	0.88	2.22	3.058 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O1	0.88	1.90	2.594 (2)	135
N5—H5⋯N3i	0.88	2.22	3.058 (2)	158

Symmetry code: (i) .