N-(3-Meth-oxy-phen-yl)-4-{4-methyl-2-[(meth-yl)(4-methyl-phen-yl)amino]-1,3-thia-zol-5-yl}pyrimidin-2-amine.

The asymmetric unit of the title compound, C(23)H(23)N(5)OS, contains two independent mol-ecules. In one mol-ecule, the thia-zole and pyrimidine rings are almost co-planar, making a dihedral angle of 2.48 (8)°. In the other mol-ecule, the corresponding dihedral angle is 12.82 (8)°. The crystal structure is stabilized by weak inter-molecular N-H⋯N and C-H⋯O inter-actions that extend along the b axis.

Related literature

For general background to the biological activity of thia­zole derivatives, see: Narayana et al. (2004 ▶). For the synthesis of the title compound, see: Bredereck et al. (1964 ▶).

Experimental

Crystal data

C23H23N5OS

M = 417.52

Triclinic,

a = 10.280 (3) Å

b = 12.413 (2) Å

c = 17.671 (4) Å

α = 74.290 (9)°

β = 87.96 (1)°

γ = 68.281 (7)°

V = 2011.3 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 153 K

0.40 × 0.40 × 0.23 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008 ▶) T min = 0.929, T max = 0.958

19475 measured reflections

9061 independent reflections

6741 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.115

S = 1.03

9061 reflections

551 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810053559/ng5080sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053559/ng5080Isup2.hkl

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

C23H23N5OS	Z = 4
Mr = 417.52	F(000) = 880
Triclinic, P1	Dx = 1.379 Mg m−3
Hall symbol: -P 1	Melting point = 456–453 K
a = 10.280 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.413 (2) Å	Cell parameters from 5913 reflections
c = 17.671 (4) Å	θ = 3.0–27.5°
α = 74.290 (9)°	µ = 0.19 mm−1
β = 87.96 (1)°	T = 153 K
γ = 68.281 (7)°	Block, yellow
V = 2011.3 (8) Å3	0.40 × 0.40 × 0.23 mm

Rigaku AFC10/Saturn724+ diffractometer	9061 independent reflections
Radiation source: fine-focus sealed tube	6741 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.1°
phi and ω scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008)	k = −16→12
Tmin = 0.929, Tmax = 0.958	l = −22→21
19475 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0641P)2] where P = (Fo2 + 2Fc2)/3
9061 reflections	(Δ/σ)max = 0.002
551 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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
S1	0.50315 (4)	0.38212 (4)	0.11927 (2)	0.02004 (11)
O1	0.31361 (12)	0.76460 (10)	0.16457 (7)	0.0297 (3)
N1	0.74892 (14)	0.22921 (12)	0.20606 (8)	0.0237 (3)
N2	0.66177 (14)	0.16781 (12)	0.11226 (8)	0.0215 (3)
N3	0.07766 (14)	0.54098 (12)	−0.08838 (8)	0.0226 (3)
N4	0.25101 (14)	0.50344 (11)	0.01314 (7)	0.0183 (3)
C1	0.61409 (18)	0.34713 (15)	0.29291 (9)	0.0233 (4)
H1	0.5369	0.3255	0.2855	0.028*
C2	0.60597 (19)	0.41897 (16)	0.34179 (10)	0.0287 (4)
H2	0.5222	0.4465	0.3674	0.034*
C3	0.7163 (2)	0.45221 (16)	0.35466 (10)	0.0301 (4)
C4	0.8380 (2)	0.40956 (16)	0.31677 (10)	0.0307 (4)
H4	0.9158	0.4298	0.3252	0.037*
C5	0.84791 (18)	0.33830 (16)	0.26710 (10)	0.0264 (4)
H5	0.9317	0.3108	0.2414	0.032*
C6	0.73559 (17)	0.30653 (14)	0.25448 (9)	0.0202 (3)
C7	0.64954 (17)	0.24899 (14)	0.14957 (9)	0.0204 (3)
C8	0.55242 (17)	0.20873 (14)	0.05698 (9)	0.0203 (3)
C9	0.45492 (16)	0.32321 (14)	0.05084 (9)	0.0186 (3)
C10	0.32638 (16)	0.39460 (14)	0.00112 (9)	0.0186 (3)
C11	0.27980 (18)	0.35759 (15)	−0.05700 (10)	0.0257 (4)
H11	0.3320	0.2823	−0.0668	0.031*
C12	0.15554 (18)	0.43451 (15)	−0.09934 (10)	0.0266 (4)
H12	0.1230	0.4102	−0.1391	0.032*
C13	0.13195 (16)	0.57067 (14)	−0.03208 (9)	0.0191 (3)
C14	0.06599 (17)	0.74316 (14)	0.02929 (9)	0.0202 (3)
C15	−0.05486 (18)	0.83747 (15)	0.03962 (10)	0.0272 (4)
H15	−0.1416	0.8547	0.0126	0.033*
C16	−0.04857 (19)	0.90526 (16)	0.08867 (10)	0.0316 (4)
H16	−0.1305	0.9703	0.0941	0.038*
C17	0.07593 (19)	0.87930 (15)	0.12995 (10)	0.0278 (4)
H17	0.0801	0.9256	0.1641	0.033*
C18	0.19478 (17)	0.78470 (14)	0.12089 (10)	0.0225 (4)
C19	0.19246 (17)	0.71745 (14)	0.07009 (9)	0.0213 (4)
H19	0.2757	0.6549	0.0632	0.026*
C20	0.7059 (3)	0.52907 (19)	0.40976 (12)	0.0483 (6)
H20A	0.7917	0.5462	0.4096	0.058*
H20B	0.6946	0.4857	0.4633	0.058*
H20C	0.6248	0.6051	0.3921	0.058*
C21	0.87705 (18)	0.12023 (16)	0.21626 (11)	0.0303 (4)
H21A	0.8514	0.0509	0.2184	0.036*
H21B	0.9303	0.1054	0.2654	0.036*
H21C	0.9348	0.1318	0.1717	0.036*
C22	0.55248 (19)	0.12289 (15)	0.01110 (10)	0.0276 (4)
H22A	0.6287	0.0447	0.0330	0.033*
H22B	0.5664	0.1557	−0.0442	0.033*
H22C	0.4624	0.1123	0.0147	0.033*
C23	0.42224 (18)	0.64788 (16)	0.17922 (11)	0.0312 (4)
H23A	0.3823	0.5860	0.1995	0.037*
H23B	0.4933	0.6396	0.2182	0.037*
H23C	0.4658	0.6378	0.1301	0.037*
S1'	0.62905 (4)	0.02186 (4)	0.35481 (2)	0.02269 (11)
O1'	0.32556 (14)	0.34116 (11)	0.45343 (7)	0.0364 (3)
N1'	0.86877 (15)	−0.12792 (13)	0.44911 (8)	0.0268 (3)
N2'	0.81090 (15)	−0.18076 (13)	0.34154 (9)	0.0273 (3)
N3'	0.21894 (15)	0.16941 (12)	0.14055 (8)	0.0236 (3)
N4'	0.39489 (14)	0.14313 (11)	0.23753 (8)	0.0188 (3)
C1'	0.80415 (18)	0.07463 (16)	0.46503 (10)	0.0269 (4)
H1'	0.8030	0.1065	0.4096	0.032*
C2'	0.7700 (2)	0.15134 (17)	0.51301 (11)	0.0312 (4)
H2'	0.7424	0.2357	0.4895	0.037*
C3'	0.7748 (2)	0.10854 (18)	0.59446 (11)	0.0336 (4)
C4'	0.8157 (2)	−0.01508 (18)	0.62604 (11)	0.0324 (4)
H4'	0.8218	−0.0473	0.6816	0.039*
C5'	0.84775 (19)	−0.09272 (17)	0.57929 (10)	0.0279 (4)
H5'	0.8753	−0.1770	0.6030	0.033*
C6'	0.84012 (17)	−0.04864 (16)	0.49739 (10)	0.0250 (4)
C7'	0.78435 (17)	−0.10428 (15)	0.38390 (10)	0.0237 (4)
C8'	0.70529 (18)	−0.14324 (15)	0.28392 (10)	0.0259 (4)
C9'	0.59585 (17)	−0.03712 (14)	0.28235 (9)	0.0212 (4)
C10'	0.46677 (17)	0.02952 (14)	0.23224 (9)	0.0204 (3)
C11'	0.41421 (19)	−0.01837 (16)	0.18333 (10)	0.0269 (4)
H11'	0.4618	−0.0989	0.1807	0.032*
C12'	0.29073 (19)	0.05571 (15)	0.13900 (10)	0.0270 (4)
H12'	0.2542	0.0242	0.1052	0.032*
C13'	0.27571 (17)	0.20653 (14)	0.19190 (9)	0.0195 (3)
C14'	0.20829 (16)	0.38181 (14)	0.24965 (9)	0.0194 (3)
C15'	0.13941 (18)	0.50655 (15)	0.22759 (10)	0.0260 (4)
H15'	0.0979	0.5474	0.1755	0.031*
C16'	0.1311 (2)	0.57126 (16)	0.28114 (12)	0.0328 (4)
H16'	0.0825	0.6563	0.2658	0.039*
C17'	0.1926 (2)	0.51390 (16)	0.35649 (11)	0.0327 (4)
H17'	0.1850	0.5586	0.3935	0.039*
C18'	0.26553 (18)	0.39037 (16)	0.37766 (10)	0.0251 (4)
C19'	0.27451 (17)	0.32300 (15)	0.32526 (9)	0.0210 (3)
H19'	0.3249	0.2382	0.3405	0.025*
C20'	0.7379 (3)	0.1922 (2)	0.64597 (13)	0.0567 (7)
H20D	0.6760	0.1704	0.6856	0.068*
H20E	0.6897	0.2754	0.6136	0.068*
H20F	0.8238	0.1856	0.6724	0.068*
C21'	0.96868 (19)	−0.25356 (16)	0.47869 (12)	0.0358 (5)
H21D	0.9171	−0.3061	0.5006	0.043*
H21E	1.0339	−0.2588	0.5199	0.043*
H21F	1.0214	−0.2794	0.4353	0.043*
C22'	0.7241 (2)	−0.22037 (18)	0.22881 (12)	0.0422 (5)
H22D	0.8231	−0.2735	0.2320	0.051*
H22E	0.6952	−0.1686	0.1747	0.051*
H22F	0.6664	−0.2693	0.2438	0.051*
C23'	0.4145 (2)	0.21765 (16)	0.47661 (10)	0.0311 (4)
H23D	0.3615	0.1684	0.4712	0.037*
H23E	0.4501	0.1951	0.5317	0.037*
H23F	0.4936	0.2039	0.4430	0.037*
N5	0.05080 (14)	0.68186 (12)	−0.02343 (8)	0.0225 (3)
H0	−0.0238	0.7215	−0.0569	0.036 (6)*
N5'	0.19792 (14)	0.32157 (12)	0.19486 (8)	0.0212 (3)
H0'	0.1314	0.3641	0.1567	0.029 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.01671 (19)	0.0193 (2)	0.0227 (2)	−0.00196 (15)	−0.00337 (16)	−0.00978 (17)
O1	0.0243 (6)	0.0262 (7)	0.0397 (7)	−0.0040 (5)	−0.0083 (6)	−0.0170 (6)
N1	0.0176 (7)	0.0247 (8)	0.0249 (7)	0.0006 (6)	−0.0038 (6)	−0.0121 (6)
N2	0.0193 (7)	0.0222 (7)	0.0209 (7)	−0.0032 (5)	−0.0003 (6)	−0.0090 (6)
N3	0.0186 (7)	0.0256 (8)	0.0212 (7)	−0.0033 (6)	−0.0033 (6)	−0.0094 (6)
N4	0.0169 (6)	0.0182 (7)	0.0180 (7)	−0.0034 (5)	0.0000 (5)	−0.0067 (5)
C1	0.0204 (8)	0.0272 (9)	0.0201 (8)	−0.0070 (7)	−0.0018 (7)	−0.0053 (7)
C2	0.0279 (9)	0.0303 (10)	0.0222 (9)	−0.0042 (7)	0.0002 (7)	−0.0076 (8)
C3	0.0407 (11)	0.0258 (9)	0.0211 (9)	−0.0085 (8)	−0.0074 (8)	−0.0065 (7)
C4	0.0348 (10)	0.0340 (10)	0.0270 (9)	−0.0183 (8)	−0.0060 (8)	−0.0056 (8)
C5	0.0233 (9)	0.0352 (10)	0.0213 (9)	−0.0132 (7)	0.0009 (7)	−0.0059 (8)
C6	0.0199 (8)	0.0206 (8)	0.0163 (8)	−0.0041 (6)	−0.0031 (6)	−0.0036 (7)
C7	0.0177 (8)	0.0201 (8)	0.0207 (8)	−0.0041 (6)	0.0008 (6)	−0.0052 (7)
C8	0.0205 (8)	0.0204 (8)	0.0196 (8)	−0.0053 (6)	0.0023 (6)	−0.0084 (7)
C9	0.0179 (8)	0.0200 (8)	0.0185 (8)	−0.0054 (6)	0.0003 (6)	−0.0084 (7)
C10	0.0165 (7)	0.0203 (8)	0.0186 (8)	−0.0055 (6)	0.0018 (6)	−0.0071 (7)
C11	0.0212 (8)	0.0255 (9)	0.0292 (9)	−0.0010 (7)	−0.0036 (7)	−0.0160 (8)
C12	0.0244 (9)	0.0309 (10)	0.0253 (9)	−0.0064 (7)	−0.0042 (7)	−0.0141 (8)
C13	0.0181 (8)	0.0217 (8)	0.0162 (8)	−0.0061 (6)	0.0017 (6)	−0.0054 (6)
C14	0.0224 (8)	0.0186 (8)	0.0178 (8)	−0.0044 (6)	−0.0012 (7)	−0.0064 (7)
C15	0.0222 (9)	0.0257 (9)	0.0271 (9)	0.0008 (7)	−0.0066 (7)	−0.0099 (8)
C16	0.0251 (9)	0.0278 (10)	0.0356 (10)	0.0027 (7)	−0.0046 (8)	−0.0160 (8)
C17	0.0290 (9)	0.0237 (9)	0.0311 (10)	−0.0038 (7)	−0.0019 (8)	−0.0162 (8)
C18	0.0218 (8)	0.0205 (8)	0.0252 (9)	−0.0073 (7)	−0.0023 (7)	−0.0064 (7)
C19	0.0190 (8)	0.0201 (8)	0.0233 (8)	−0.0041 (6)	0.0005 (7)	−0.0081 (7)
C20	0.0673 (16)	0.0416 (12)	0.0410 (12)	−0.0169 (11)	−0.0073 (11)	−0.0226 (10)
C21	0.0207 (9)	0.0302 (10)	0.0326 (10)	0.0022 (7)	−0.0060 (8)	−0.0126 (8)
C22	0.0285 (9)	0.0221 (9)	0.0294 (9)	−0.0019 (7)	−0.0033 (8)	−0.0130 (7)
C23	0.0217 (9)	0.0282 (10)	0.0412 (11)	−0.0024 (7)	−0.0087 (8)	−0.0139 (8)
S1'	0.0201 (2)	0.0222 (2)	0.0229 (2)	−0.00219 (16)	−0.00535 (17)	−0.00906 (17)
O1'	0.0433 (8)	0.0365 (8)	0.0248 (7)	−0.0039 (6)	−0.0043 (6)	−0.0159 (6)
N1'	0.0207 (7)	0.0268 (8)	0.0279 (8)	−0.0031 (6)	−0.0071 (6)	−0.0064 (6)
N2'	0.0223 (7)	0.0244 (8)	0.0308 (8)	−0.0016 (6)	−0.0017 (6)	−0.0104 (7)
N3'	0.0215 (7)	0.0252 (8)	0.0238 (7)	−0.0068 (6)	−0.0044 (6)	−0.0081 (6)
N4'	0.0176 (7)	0.0187 (7)	0.0187 (7)	−0.0053 (5)	−0.0003 (5)	−0.0049 (5)
C1'	0.0254 (9)	0.0333 (10)	0.0225 (9)	−0.0136 (7)	−0.0051 (7)	−0.0040 (8)
C2'	0.0342 (10)	0.0330 (10)	0.0298 (10)	−0.0180 (8)	−0.0047 (8)	−0.0057 (8)
C3'	0.0375 (11)	0.0421 (12)	0.0317 (10)	−0.0235 (9)	0.0017 (8)	−0.0145 (9)
C4'	0.0332 (10)	0.0455 (12)	0.0233 (9)	−0.0225 (9)	−0.0010 (8)	−0.0057 (8)
C5'	0.0252 (9)	0.0315 (10)	0.0254 (9)	−0.0137 (7)	−0.0068 (7)	−0.0001 (8)
C6'	0.0160 (8)	0.0310 (10)	0.0280 (9)	−0.0091 (7)	−0.0041 (7)	−0.0071 (8)
C7'	0.0194 (8)	0.0235 (9)	0.0250 (9)	−0.0052 (7)	−0.0009 (7)	−0.0052 (7)
C8'	0.0240 (9)	0.0236 (9)	0.0286 (9)	−0.0041 (7)	0.0000 (7)	−0.0112 (7)
C9'	0.0229 (8)	0.0195 (8)	0.0200 (8)	−0.0057 (7)	−0.0022 (7)	−0.0062 (7)
C10'	0.0221 (8)	0.0208 (8)	0.0175 (8)	−0.0072 (6)	0.0006 (7)	−0.0050 (7)
C11'	0.0287 (9)	0.0236 (9)	0.0281 (9)	−0.0069 (7)	−0.0039 (8)	−0.0101 (7)
C12'	0.0310 (10)	0.0288 (10)	0.0245 (9)	−0.0114 (8)	−0.0038 (8)	−0.0114 (8)
C13'	0.0190 (8)	0.0224 (8)	0.0165 (8)	−0.0081 (6)	0.0017 (6)	−0.0043 (7)
C14'	0.0133 (7)	0.0231 (8)	0.0230 (8)	−0.0077 (6)	0.0025 (6)	−0.0070 (7)
C15'	0.0223 (9)	0.0244 (9)	0.0295 (9)	−0.0076 (7)	−0.0030 (7)	−0.0057 (7)
C16'	0.0289 (10)	0.0208 (9)	0.0463 (12)	−0.0051 (7)	−0.0039 (9)	−0.0105 (8)
C17'	0.0318 (10)	0.0302 (10)	0.0396 (11)	−0.0071 (8)	0.0013 (9)	−0.0213 (9)
C18'	0.0223 (8)	0.0304 (9)	0.0239 (9)	−0.0086 (7)	0.0015 (7)	−0.0114 (7)
C19'	0.0178 (8)	0.0220 (8)	0.0233 (8)	−0.0063 (6)	0.0033 (7)	−0.0082 (7)
C20'	0.091 (2)	0.0563 (15)	0.0408 (13)	−0.0408 (14)	0.0134 (13)	−0.0252 (11)
C21'	0.0256 (10)	0.0303 (10)	0.0405 (11)	0.0005 (8)	−0.0110 (9)	−0.0064 (9)
C22'	0.0319 (11)	0.0401 (12)	0.0520 (13)	0.0012 (9)	−0.0059 (10)	−0.0285 (10)
C23'	0.0325 (10)	0.0335 (10)	0.0235 (9)	−0.0081 (8)	−0.0051 (8)	−0.0073 (8)
N5	0.0193 (7)	0.0212 (7)	0.0225 (7)	−0.0002 (6)	−0.0070 (6)	−0.0083 (6)
N5'	0.0179 (7)	0.0220 (7)	0.0209 (7)	−0.0035 (5)	−0.0043 (6)	−0.0064 (6)

S1—C7	1.7377 (16)	S1'—C7'	1.7427 (17)
S1—C9	1.7414 (16)	O1'—C18'	1.372 (2)
O1—C18	1.3739 (19)	O1'—C23'	1.416 (2)
O1—C23	1.4259 (19)	N1'—C7'	1.366 (2)
N1—C7	1.362 (2)	N1'—C6'	1.416 (2)
N1—C6	1.418 (2)	N1'—C21'	1.474 (2)
N1—C21	1.4709 (19)	N2'—C7'	1.309 (2)
N2—C7	1.314 (2)	N2'—C8'	1.371 (2)
N2—C8	1.365 (2)	N3'—C12'	1.336 (2)
N3—C12	1.330 (2)	N3'—C13'	1.356 (2)
N3—C13	1.352 (2)	N4'—C13'	1.336 (2)
N4—C13	1.3362 (19)	N4'—C10'	1.356 (2)
N4—C10	1.3563 (19)	C1'—C2'	1.385 (2)
C1—C2	1.380 (2)	C1'—C6'	1.388 (2)
C1—C6	1.391 (2)	C1'—H1'	0.9500
C1—H1	0.9500	C2'—C3'	1.389 (3)
C2—C3	1.387 (3)	C2'—H2'	0.9500
C2—H2	0.9500	C3'—C4'	1.385 (3)
C3—C4	1.391 (3)	C3'—C20'	1.499 (3)
C3—C20	1.513 (2)	C4'—C5'	1.377 (3)
C4—C5	1.382 (2)	C4'—H4'	0.9500
C4—H4	0.9500	C5'—C6'	1.395 (2)
C5—C6	1.393 (2)	C5'—H5'	0.9500
C5—H5	0.9500	C8'—C9'	1.374 (2)
C8—C9	1.381 (2)	C8'—C22'	1.502 (2)
C8—C22	1.503 (2)	C9'—C10'	1.450 (2)
C9—C10	1.448 (2)	C10'—C11'	1.393 (2)
C10—C11	1.396 (2)	C11'—C12'	1.374 (2)
C11—C12	1.372 (2)	C11'—H11'	0.9500
C11—H11	0.9500	C12'—H12'	0.9500
C12—H12	0.9500	C13'—N5'	1.369 (2)
C13—N5	1.370 (2)	C14'—C15'	1.390 (2)
C14—C19	1.395 (2)	C14'—C19'	1.396 (2)
C14—N5	1.398 (2)	C14'—N5'	1.402 (2)
C14—C15	1.404 (2)	C15'—C16'	1.380 (2)
C15—C16	1.379 (2)	C15'—H15'	0.9500
C15—H15	0.9500	C16'—C17'	1.376 (3)
C16—C17	1.381 (2)	C16'—H16'	0.9500
C16—H16	0.9500	C17'—C18'	1.383 (2)
C17—C18	1.387 (2)	C17'—H17'	0.9500
C17—H17	0.9500	C18'—C19'	1.386 (2)
C18—C19	1.388 (2)	C19'—H19'	0.9500
C19—H19	0.9500	C20'—H20D	0.9800
C20—H20A	0.9800	C20'—H20E	0.9800
C20—H20B	0.9800	C20'—H20F	0.9800
C20—H20C	0.9800	C21'—H21D	0.9800
C21—H21A	0.9800	C21'—H21E	0.9800
C21—H21B	0.9800	C21'—H21F	0.9800
C21—H21C	0.9800	C22'—H22D	0.9800
C22—H22A	0.9800	C22'—H22E	0.9800
C22—H22B	0.9800	C22'—H22F	0.9800
C22—H22C	0.9800	C23'—H23D	0.9800
C23—H23A	0.9800	C23'—H23E	0.9800
C23—H23B	0.9800	C23'—H23F	0.9800
C23—H23C	0.9800	N5—H0	0.8800
S1'—C9'	1.7367 (16)	N5'—H0'	0.8800
C7—S1—C9	88.64 (8)	C7'—N1'—C21'	115.57 (15)
C18—O1—C23	116.99 (13)	C6'—N1'—C21'	119.97 (14)
C7—N1—C6	124.09 (13)	C7'—N2'—C8'	110.83 (14)
C7—N1—C21	116.77 (14)	C12'—N3'—C13'	114.45 (14)
C6—N1—C21	119.14 (13)	C13'—N4'—C10'	116.72 (14)
C7—N2—C8	110.62 (13)	C2'—C1'—C6'	120.40 (16)
C12—N3—C13	114.57 (13)	C2'—C1'—H1'	119.8
C13—N4—C10	117.02 (14)	C6'—C1'—H1'	119.8
C2—C1—C6	119.79 (17)	C1'—C2'—C3'	121.91 (18)
C2—C1—H1	120.1	C1'—C2'—H2'	119.0
C6—C1—H1	120.1	C3'—C2'—H2'	119.0
C1—C2—C3	122.08 (17)	C4'—C3'—C2'	116.98 (18)
C1—C2—H2	119.0	C4'—C3'—C20'	121.47 (18)
C3—C2—H2	119.0	C2'—C3'—C20'	121.55 (18)
C2—C3—C4	117.55 (17)	C5'—C4'—C3'	122.02 (17)
C2—C3—C20	121.09 (19)	C5'—C4'—H4'	119.0
C4—C3—C20	121.34 (19)	C3'—C4'—H4'	119.0
C5—C4—C3	121.29 (17)	C4'—C5'—C6'	120.58 (17)
C5—C4—H4	119.4	C4'—C5'—H5'	119.7
C3—C4—H4	119.4	C6'—C5'—H5'	119.7
C4—C5—C6	120.32 (17)	C1'—C6'—C5'	118.04 (16)
C4—C5—H5	119.8	C1'—C6'—N1'	121.29 (15)
C6—C5—H5	119.8	C5'—C6'—N1'	120.66 (16)
C1—C6—C5	118.96 (16)	N2'—C7'—N1'	121.33 (15)
C1—C6—N1	121.09 (15)	N2'—C7'—S1'	115.06 (12)
C5—C6—N1	119.88 (15)	N1'—C7'—S1'	123.46 (13)
N2—C7—N1	121.04 (14)	N2'—C8'—C9'	115.64 (15)
N2—C7—S1	115.41 (12)	N2'—C8'—C22'	116.69 (15)
N1—C7—S1	123.51 (13)	C9'—C8'—C22'	127.65 (16)
N2—C8—C9	115.91 (14)	C8'—C9'—C10'	131.90 (15)
N2—C8—C22	115.90 (14)	C8'—C9'—S1'	109.75 (12)
C9—C8—C22	128.19 (15)	C10'—C9'—S1'	118.34 (12)
C8—C9—C10	131.61 (15)	N4'—C10'—C11'	120.66 (14)
C8—C9—S1	109.42 (12)	N4'—C10'—C9'	115.53 (14)
C10—C9—S1	118.95 (12)	C11'—C10'—C9'	123.78 (15)
N4—C10—C11	120.22 (14)	C12'—C11'—C10'	117.26 (16)
N4—C10—C9	116.07 (14)	C12'—C11'—H11'	121.4
C11—C10—C9	123.70 (14)	C10'—C11'—H11'	121.4
C12—C11—C10	117.24 (15)	N3'—C12'—C11'	123.97 (16)
C12—C11—H11	121.4	N3'—C12'—H12'	118.0
C10—C11—H11	121.4	C11'—C12'—H12'	118.0
N3—C12—C11	124.25 (15)	N4'—C13'—N3'	126.86 (15)
N3—C12—H12	117.9	N4'—C13'—N5'	119.53 (14)
C11—C12—H12	117.9	N3'—C13'—N5'	113.61 (14)
N4—C13—N3	126.68 (14)	C15'—C14'—C19'	119.57 (15)
N4—C13—N5	120.21 (14)	C15'—C14'—N5'	116.54 (14)
N3—C13—N5	113.11 (13)	C19'—C14'—N5'	123.74 (14)
C19—C14—N5	124.14 (14)	C16'—C15'—C14'	120.21 (16)
C19—C14—C15	119.27 (15)	C16'—C15'—H15'	119.9
N5—C14—C15	116.57 (14)	C14'—C15'—H15'	119.9
C16—C15—C14	120.50 (16)	C17'—C16'—C15'	120.70 (17)
C16—C15—H15	119.7	C17'—C16'—H16'	119.6
C14—C15—H15	119.7	C15'—C16'—H16'	119.6
C15—C16—C17	120.48 (16)	C16'—C17'—C18'	119.15 (17)
C15—C16—H16	119.8	C16'—C17'—H17'	120.4
C17—C16—H16	119.8	C18'—C17'—H17'	120.4
C16—C17—C18	119.04 (16)	O1'—C18'—C17'	115.16 (15)
C16—C17—H17	120.5	O1'—C18'—C19'	123.49 (15)
C18—C17—H17	120.5	C17'—C18'—C19'	121.34 (16)
O1—C18—C17	115.16 (15)	C18'—C19'—C14'	118.95 (15)
O1—C18—C19	123.15 (14)	C18'—C19'—H19'	120.5
C17—C18—C19	121.68 (15)	C14'—C19'—H19'	120.5
C18—C19—C14	118.98 (15)	C3'—C20'—H20D	109.5
C18—C19—H19	120.5	C3'—C20'—H20E	109.5
C14—C19—H19	120.5	H20D—C20'—H20E	109.5
C3—C20—H20A	109.5	C3'—C20'—H20F	109.5
C3—C20—H20B	109.5	H20D—C20'—H20F	109.5
H20A—C20—H20B	109.5	H20E—C20'—H20F	109.5
C3—C20—H20C	109.5	N1'—C21'—H21D	109.5
H20A—C20—H20C	109.5	N1'—C21'—H21E	109.5
H20B—C20—H20C	109.5	H21D—C21'—H21E	109.5
N1—C21—H21A	109.5	N1'—C21'—H21F	109.5
N1—C21—H21B	109.5	H21D—C21'—H21F	109.5
H21A—C21—H21B	109.5	H21E—C21'—H21F	109.5
N1—C21—H21C	109.5	C8'—C22'—H22D	109.5
H21A—C21—H21C	109.5	C8'—C22'—H22E	109.5
H21B—C21—H21C	109.5	H22D—C22'—H22E	109.5
C8—C22—H22A	109.5	C8'—C22'—H22F	109.5
C8—C22—H22B	109.5	H22D—C22'—H22F	109.5
H22A—C22—H22B	109.5	H22E—C22'—H22F	109.5
C8—C22—H22C	109.5	O1'—C23'—H23D	109.5
H22A—C22—H22C	109.5	O1'—C23'—H23E	109.5
H22B—C22—H22C	109.5	H23D—C23'—H23E	109.5
O1—C23—H23A	109.5	O1'—C23'—H23F	109.5
O1—C23—H23B	109.5	H23D—C23'—H23F	109.5
H23A—C23—H23B	109.5	H23E—C23'—H23F	109.5
O1—C23—H23C	109.5	C13—N5—C14	131.15 (13)
H23A—C23—H23C	109.5	C13—N5—H0	114.4
H23B—C23—H23C	109.5	C14—N5—H0	114.4
C9'—S1'—C7'	88.66 (8)	C13'—N5'—C14'	129.69 (13)
C18'—O1'—C23'	118.32 (13)	C13'—N5'—H0'	115.2
C7'—N1'—C6'	122.53 (14)	C14'—N5'—H0'	115.2
C6—C1—C2—C3	−0.4 (3)	C20'—C3'—C4'—C5'	178.9 (2)
C1—C2—C3—C4	−0.5 (3)	C3'—C4'—C5'—C6'	0.1 (3)
C1—C2—C3—C20	−178.81 (17)	C2'—C1'—C6'—C5'	−3.3 (3)
C2—C3—C4—C5	1.0 (3)	C2'—C1'—C6'—N1'	176.88 (16)
C20—C3—C4—C5	179.31 (17)	C4'—C5'—C6'—C1'	2.2 (3)
C3—C4—C5—C6	−0.6 (3)	C4'—C5'—C6'—N1'	−178.01 (16)
C2—C1—C6—C5	0.8 (2)	C7'—N1'—C6'—C1'	−46.7 (3)
C2—C1—C6—N1	177.79 (14)	C21'—N1'—C6'—C1'	149.80 (17)
C4—C5—C6—C1	−0.3 (2)	C7'—N1'—C6'—C5'	133.47 (18)
C4—C5—C6—N1	−177.33 (15)	C21'—N1'—C6'—C5'	−30.0 (2)
C7—N1—C6—C1	48.2 (2)	C8'—N2'—C7'—N1'	174.26 (16)
C21—N1—C6—C1	−131.79 (17)	C8'—N2'—C7'—S1'	−1.4 (2)
C7—N1—C6—C5	−134.82 (18)	C6'—N1'—C7'—N2'	−177.96 (16)
C21—N1—C6—C5	45.2 (2)	C21'—N1'—C7'—N2'	−13.8 (3)
C8—N2—C7—N1	−178.21 (15)	C6'—N1'—C7'—S1'	−2.7 (3)
C8—N2—C7—S1	−0.28 (19)	C21'—N1'—C7'—S1'	161.47 (14)
C6—N1—C7—N2	−172.95 (15)	C9'—S1'—C7'—N2'	2.15 (15)
C21—N1—C7—N2	7.1 (2)	C9'—S1'—C7'—N1'	−173.40 (17)
C6—N1—C7—S1	9.3 (2)	C7'—N2'—C8'—C9'	−0.5 (2)
C21—N1—C7—S1	−170.69 (13)	C7'—N2'—C8'—C22'	177.95 (17)
C9—S1—C7—N2	0.00 (14)	N2'—C8'—C9'—C10'	−178.95 (18)
C9—S1—C7—N1	177.87 (16)	C22'—C8'—C9'—C10'	2.9 (3)
C7—N2—C8—C9	0.5 (2)	N2'—C8'—C9'—S1'	2.0 (2)
C7—N2—C8—C22	−178.81 (15)	C22'—C8'—C9'—S1'	−176.16 (17)
N2—C8—C9—C10	−178.73 (17)	C7'—S1'—C9'—C8'	−2.23 (14)
C22—C8—C9—C10	0.5 (3)	C7'—S1'—C9'—C10'	178.60 (15)
N2—C8—C9—S1	−0.52 (19)	C13'—N4'—C10'—C11'	−2.3 (2)
C22—C8—C9—S1	178.71 (15)	C13'—N4'—C10'—C9'	179.90 (15)
C7—S1—C9—C8	0.28 (13)	C8'—C9'—C10'—N4'	−167.75 (18)
C7—S1—C9—C10	178.75 (14)	S1'—C9'—C10'—N4'	11.2 (2)
C13—N4—C10—C11	0.7 (2)	C8'—C9'—C10'—C11'	14.5 (3)
C13—N4—C10—C9	−179.93 (15)	S1'—C9'—C10'—C11'	−166.56 (14)
C8—C9—C10—N4	177.00 (17)	N4'—C10'—C11'—C12'	2.5 (3)
S1—C9—C10—N4	−1.1 (2)	C9'—C10'—C11'—C12'	−179.83 (17)
C8—C9—C10—C11	−3.7 (3)	C13'—N3'—C12'—C11'	−1.8 (3)
S1—C9—C10—C11	178.22 (14)	C10'—C11'—C12'—N3'	−0.4 (3)
N4—C10—C11—C12	−1.0 (3)	C10'—N4'—C13'—N3'	−0.2 (3)
C9—C10—C11—C12	179.69 (17)	C10'—N4'—C13'—N5'	179.63 (15)
C13—N3—C12—C11	1.3 (3)	C12'—N3'—C13'—N4'	2.2 (3)
C10—C11—C12—N3	−0.1 (3)	C12'—N3'—C13'—N5'	−177.63 (15)
C10—N4—C13—N3	0.7 (3)	C19'—C14'—C15'—C16'	−2.9 (3)
C10—N4—C13—N5	−179.70 (15)	N5'—C14'—C15'—C16'	172.79 (16)
C12—N3—C13—N4	−1.7 (3)	C14'—C15'—C16'—C17'	1.1 (3)
C12—N3—C13—N5	178.67 (15)	C15'—C16'—C17'—C18'	1.3 (3)
C19—C14—C15—C16	0.9 (3)	C23'—O1'—C18'—C17'	−173.22 (17)
N5—C14—C15—C16	−178.00 (16)	C23'—O1'—C18'—C19'	7.4 (3)
C14—C15—C16—C17	−1.7 (3)	C16'—C17'—C18'—O1'	178.81 (18)
C15—C16—C17—C18	0.5 (3)	C16'—C17'—C18'—C19'	−1.8 (3)
C23—O1—C18—C17	158.88 (17)	O1'—C18'—C19'—C14'	179.33 (16)
C23—O1—C18—C19	−22.2 (2)	C17'—C18'—C19'—C14'	0.0 (3)
C16—C17—C18—O1	−179.50 (16)	C15'—C14'—C19'—C18'	2.3 (2)
C16—C17—C18—C19	1.5 (3)	N5'—C14'—C19'—C18'	−173.03 (15)
O1—C18—C19—C14	178.81 (15)	N4—C13—N5—C14	−2.6 (3)
C17—C18—C19—C14	−2.3 (3)	N3—C13—N5—C14	177.09 (16)
N5—C14—C19—C18	179.88 (15)	C19—C14—N5—C13	20.4 (3)
C15—C14—C19—C18	1.1 (3)	C15—C14—N5—C13	−160.71 (17)
C6'—C1'—C2'—C3'	2.3 (3)	N4'—C13'—N5'—C14'	−12.8 (3)
C1'—C2'—C3'—C4'	0.0 (3)	N3'—C13'—N5'—C14'	167.01 (16)
C1'—C2'—C3'—C20'	179.9 (2)	C15'—C14'—N5'—C13'	164.55 (17)
C2'—C3'—C4'—C5'	−1.2 (3)	C19'—C14'—N5'—C13'	−20.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H0···N3'i	0.88	2.27	3.151 (2)	177
N5'—H0'···N3i	0.88	2.24	3.089 (2)	164
C22—H22B···O1ii	0.98	2.57	3.500 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H0⋯N3′i	0.88	2.27	3.151 (2)	177
N5′—H0′⋯N3i	0.88	2.24	3.089 (2)	164
C22—H22B⋯O1ii	0.98	2.57	3.500 (2)	159

Symmetry codes: (i) ; (ii) .