Sulfur as hydrogen-bond acceptor in cocrystals of 2-thio-modified thymine

Doubly and triply hydrogen-bonded supra­molecular synthons are of particular inter­est for the rational design of crystal and cocrystal structures in crystal engineering since they show a high robustness due to their high stability and good reliability. The compound 5-methyl-2-thio­uracil (2-thio­thymine) contains an ADA hydrogen-bonding site (A = acceptor and D = donor) if the S atom is considered as an acceptor. We report herein the results of cocrystallization experiments with the coformers 2,4-di­amino­pyrimidine, 2,4-di­amino-6-phenyl-1,3,5-triazine, 6-amino-3H-isocytosine and melamine, which contain complementary DAD hydrogen-bonding sites and, therefore, should be capable of forming a mixed ADA–DAD N—H...S/N—H...N/N—H...O synthon (denoted synthon 3s_{N·S;N·N;N·O}), consisting of three different hydrogen bonds with 5-methyl-2-thio­uracil. The experiments yielded one cocrystal and five solvated cocrystals, namely 5-methyl-2-thio­uracil–2,4-di­amino­pyrimidine (1/2), C₅H₆N₂OS·2C₄H₆N₄, (I), 5-methyl-2-thio­uracil–2,4-di­amino­pyrimidine–N,N-di­methyl­formamide (2/2/1), 2C₅H₆N₂OS·2C₄H₆N₄·C₃H₇NO, (II), 5-methyl-2-thio­uracil–2,4-di­amino-6-phenyl-1,3,5-triazine–N,N-di­methyl­formamide (2/2/1), 2C₅H₆N₂OS·2C₉H₉N₅·C₃H₇NO, (III), 5-methyl-2-thio­uracil–6-amino-3H-isocytosine–N,N-di­methyl­formamide (2/2/1), (IV), 2C₅H₆N₂OS·2C₄H₆N₄O·C₃H₇NO, (IV), 5-methyl-2-thio­uracil–6-amino-3H-isocytosine–N,N-di­methyl­acetamide (2/2/1), 2C₅H₆N₂OS·2C₄H₆N₄O·C₄H₉NO, (V), and 5-methyl-2-thio­uracil–melamine (3/2), 3C₅H₆N₂OS·2C₃H₆N₆, (VI). Synthon 3s_{N·S;N·N;N·O} was formed in three structures in which two-dimensional hydrogen-bonded networks are observed, while doubly hydrogen-bonded inter­actions were formed instead in the remaining three cocrystals whereby three-dimensional networks are preferred. As desired, the S atoms are involved in hydrogen-bonding inter­actions in all six structures, thus illustrating the ability of sulfur to act as a hydrogen-bond acceptor and, therefore, its value for application in crystal engineering.

Computing details

For all structures, data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Version 3.9, Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

5-Methyl-2-thiouracil–2,4-diaminopyrimidine (1/2) (I)

Crystal data

C5H6N2OS·2C4H6N4	Z = 2
Mr = 362.43	F(000) = 380
Triclinic, P1	Dx = 1.426 Mg m^−3
a = 7.7255 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1381 (14) Å	Cell parameters from 11686 reflections
c = 12.4594 (17) Å	θ = 3.4–26.2°
α = 92.241 (11)°	µ = 0.22 mm^−1
β = 104.034 (10)°	T = 173 K
γ = 97.248 (11)°	Block, colourless
V = 844.3 (2) Å^3	0.31 × 0.21 × 0.20 mm

Data collection

STOE IPDS II two-circle diffractometer	2752 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.041
ω scans	θmax = 25.9°, θmin = 3.4°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −9→8
Tmin = 0.821, Tmax = 1.000	k = −11→11
7146 measured reflections	l = −15→15
3233 independent reflections

Refinement

Refinement on F^2	10 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.093	w = 1/[σ^2(Fo^2) + (0.0526P)^2 + 0.1481P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3233 reflections	Δρmax = 0.23 e Å^−3
257 parameters	Δρmin = −0.25 e Å^−3

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1A	0.36696 (18)	0.55829 (15)	0.66190 (11)	0.0263 (3)
H1A	0.434 (2)	0.556 (2)	0.7282 (13)	0.032*
C2A	0.3463 (2)	0.43970 (17)	0.59002 (12)	0.0246 (3)
S21A	0.44038 (6)	0.28702 (5)	0.62632 (3)	0.03083 (13)
N3A	0.24595 (17)	0.45105 (14)	0.48589 (10)	0.0239 (3)
H3A	0.228 (2)	0.3744 (18)	0.4370 (14)	0.029*
C4A	0.1669 (2)	0.57323 (17)	0.44852 (12)	0.0243 (3)
O41A	0.07836 (16)	0.56900 (12)	0.35151 (9)	0.0305 (3)
C5A	0.1940 (2)	0.69727 (17)	0.52912 (12)	0.0246 (3)
C51A	0.1126 (3)	0.83359 (18)	0.49507 (14)	0.0333 (4)
H51A	0.1522	0.9104	0.5564	0.050*
H52A	−0.0191	0.8107	0.4763	0.050*
H53A	0.1514	0.8690	0.4302	0.050*
C6A	0.2927 (2)	0.68306 (18)	0.63184 (13)	0.0268 (3)
H6A	0.3117	0.7634	0.6860	0.032*
N1B	0.57109 (17)	0.59745 (15)	0.88240 (11)	0.0273 (3)
C2B	0.7191 (2)	0.54425 (17)	0.93589 (12)	0.0235 (3)
N21B	0.7726 (2)	0.43075 (15)	0.88358 (12)	0.0291 (3)
H21B	0.720 (3)	0.413 (2)	0.8126 (13)	0.035*
H22B	0.888 (2)	0.424 (2)	0.9046 (15)	0.035*
N3B	0.81924 (17)	0.58941 (14)	1.03905 (10)	0.0242 (3)
C4B	0.7641 (2)	0.69717 (18)	1.09314 (12)	0.0256 (3)
N41B	0.8598 (2)	0.74284 (18)	1.19726 (11)	0.0336 (3)
H41B	0.938 (3)	0.688 (2)	1.2337 (16)	0.040*
H42B	0.805 (3)	0.791 (2)	1.2392 (16)	0.040*
C5B	0.6133 (2)	0.76298 (18)	1.04278 (13)	0.0290 (3)
H5B	0.5764	0.8421	1.0795	0.035*
C6B	0.5225 (2)	0.70760 (18)	0.93867 (13)	0.0289 (3)
H6B	0.4185	0.7492	0.9035	0.035*
N1C	0.19948 (19)	0.21725 (15)	0.32059 (11)	0.0280 (3)
C2C	0.0924 (2)	0.20734 (16)	0.21725 (12)	0.0246 (3)
N21C	−0.02932 (19)	0.30457 (16)	0.19594 (12)	0.0296 (3)
H21C	−0.008 (3)	0.3812 (19)	0.2444 (15)	0.035*
H22C	−0.073 (3)	0.319 (2)	0.1239 (13)	0.035*
N3C	0.08906 (18)	0.10809 (14)	0.13442 (10)	0.0261 (3)
C4C	0.2033 (2)	0.00810 (17)	0.15581 (13)	0.0272 (3)
N41C	0.2012 (2)	−0.09037 (16)	0.07231 (13)	0.0341 (3)
H41C	0.114 (3)	−0.090 (2)	0.0102 (14)	0.041*
H42C	0.254 (3)	−0.169 (2)	0.0863 (17)	0.041*
C5C	0.3224 (2)	0.01019 (18)	0.26110 (14)	0.0322 (4)
H5C	0.4058	−0.0588	0.2771	0.039*
C6C	0.3129 (2)	0.11562 (18)	0.33922 (13)	0.0311 (4)
H6C	0.3912	0.1174	0.4111	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0243 (7)	0.0308 (7)	0.0209 (6)	0.0058 (5)	−0.0007 (5)	0.0002 (5)
C2A	0.0195 (7)	0.0304 (8)	0.0240 (7)	0.0043 (6)	0.0052 (6)	0.0037 (6)
S21A	0.0323 (2)	0.0341 (2)	0.0269 (2)	0.01514 (16)	0.00322 (16)	0.00457 (15)
N3A	0.0245 (7)	0.0245 (7)	0.0210 (6)	0.0059 (5)	0.0015 (5)	−0.0003 (5)
C4A	0.0222 (8)	0.0258 (8)	0.0243 (7)	0.0035 (6)	0.0046 (6)	0.0028 (6)
O41A	0.0349 (6)	0.0288 (6)	0.0235 (6)	0.0089 (5)	−0.0029 (5)	0.0017 (4)
C5A	0.0237 (8)	0.0238 (7)	0.0264 (7)	0.0030 (6)	0.0065 (6)	0.0011 (6)
C51A	0.0400 (10)	0.0253 (8)	0.0331 (8)	0.0078 (7)	0.0046 (7)	0.0016 (6)
C6A	0.0247 (8)	0.0275 (8)	0.0269 (8)	0.0015 (6)	0.0056 (6)	−0.0024 (6)
N1B	0.0221 (7)	0.0323 (7)	0.0260 (6)	0.0066 (5)	0.0015 (5)	0.0032 (5)
C2B	0.0196 (7)	0.0259 (7)	0.0250 (7)	0.0032 (6)	0.0050 (6)	0.0062 (6)
N21B	0.0253 (7)	0.0324 (7)	0.0277 (7)	0.0077 (6)	0.0017 (6)	−0.0023 (5)
N3B	0.0221 (6)	0.0282 (7)	0.0228 (6)	0.0064 (5)	0.0046 (5)	0.0042 (5)
C4B	0.0238 (8)	0.0315 (8)	0.0222 (7)	0.0050 (6)	0.0061 (6)	0.0047 (6)
N41B	0.0352 (8)	0.0439 (9)	0.0225 (7)	0.0179 (7)	0.0029 (6)	0.0002 (6)
C5B	0.0291 (8)	0.0330 (9)	0.0277 (8)	0.0121 (7)	0.0081 (6)	0.0030 (6)
C6B	0.0231 (8)	0.0350 (9)	0.0288 (8)	0.0106 (6)	0.0028 (6)	0.0071 (6)
N1C	0.0311 (7)	0.0263 (7)	0.0258 (6)	0.0046 (5)	0.0057 (5)	0.0006 (5)
C2C	0.0251 (8)	0.0225 (7)	0.0260 (7)	0.0004 (6)	0.0078 (6)	0.0013 (6)
N21C	0.0325 (8)	0.0287 (7)	0.0265 (7)	0.0093 (6)	0.0039 (6)	−0.0033 (5)
N3C	0.0282 (7)	0.0232 (6)	0.0258 (6)	0.0040 (5)	0.0050 (5)	0.0003 (5)
C4C	0.0289 (8)	0.0227 (7)	0.0306 (8)	0.0025 (6)	0.0094 (6)	0.0003 (6)
N41C	0.0387 (8)	0.0280 (7)	0.0343 (8)	0.0124 (6)	0.0037 (6)	−0.0036 (6)
C5C	0.0336 (9)	0.0276 (8)	0.0349 (9)	0.0099 (7)	0.0046 (7)	0.0038 (6)
C6C	0.0329 (9)	0.0306 (8)	0.0283 (8)	0.0049 (7)	0.0040 (7)	0.0039 (6)

Geometric parameters (Å, º)

N1A—C2A	1.347 (2)	C4B—N41B	1.349 (2)
N1A—C6A	1.365 (2)	C4B—C5B	1.401 (2)
N1A—H1A	0.865 (15)	N41B—H41B	0.886 (16)
C2A—N3A	1.356 (2)	N41B—H42B	0.881 (15)
C2A—S21A	1.6806 (16)	C5B—C6B	1.360 (2)
N3A—C4A	1.383 (2)	C5B—H5B	0.9500
N3A—H3A	0.885 (14)	C6B—H6B	0.9500
C4A—O41A	1.2324 (18)	N1C—C2C	1.344 (2)
C4A—C5A	1.444 (2)	N1C—C6C	1.345 (2)
C5A—C6A	1.342 (2)	C2C—N3C	1.3404 (19)
C5A—C51A	1.495 (2)	C2C—N21C	1.361 (2)
C51A—H51A	0.9800	N21C—H21C	0.879 (15)
C51A—H52A	0.9800	N21C—H22C	0.900 (15)
C51A—H53A	0.9800	N3C—C4C	1.339 (2)
C6A—H6A	0.9500	C4C—N41C	1.344 (2)
N1B—C2B	1.336 (2)	C4C—C5C	1.406 (2)
N1B—C6B	1.346 (2)	N41C—H41C	0.893 (16)
C2B—N3B	1.348 (2)	N41C—H42C	0.874 (16)
C2B—N21B	1.363 (2)	C5C—C6C	1.364 (2)
N21B—H21B	0.878 (15)	C5C—H5C	0.9500
N21B—H22B	0.877 (15)	C6C—H6C	0.9500
N3B—C4B	1.341 (2)
C2A—N1A—C6A	122.19 (13)	N3B—C4B—N41B	118.13 (15)
C2A—N1A—H1A	118.3 (13)	N3B—C4B—C5B	121.31 (14)
C6A—N1A—H1A	119.4 (13)	N41B—C4B—C5B	120.55 (15)
N1A—C2A—N3A	115.96 (14)	C4B—N41B—H41B	119.5 (13)
N1A—C2A—S21A	122.26 (12)	C4B—N41B—H42B	117.0 (14)
N3A—C2A—S21A	121.78 (12)	H41B—N41B—H42B	114.6 (19)
C2A—N3A—C4A	125.54 (13)	C6B—C5B—C4B	116.50 (15)
C2A—N3A—H3A	118.2 (12)	C6B—C5B—H5B	121.8
C4A—N3A—H3A	116.3 (12)	C4B—C5B—H5B	121.8
O41A—C4A—N3A	119.02 (14)	N1B—C6B—C5B	124.04 (15)
O41A—C4A—C5A	124.93 (15)	N1B—C6B—H6B	118.0
N3A—C4A—C5A	116.05 (13)	C5B—C6B—H6B	118.0
C6A—C5A—C4A	117.33 (15)	C2C—N1C—C6C	114.62 (14)
C6A—C5A—C51A	123.41 (14)	N3C—C2C—N1C	126.55 (15)
C4A—C5A—C51A	119.26 (14)	N3C—C2C—N21C	116.82 (14)
C5A—C51A—H51A	109.5	N1C—C2C—N21C	116.58 (14)
C5A—C51A—H52A	109.5	C2C—N21C—H21C	115.0 (14)
H51A—C51A—H52A	109.5	C2C—N21C—H22C	115.5 (13)
C5A—C51A—H53A	109.5	H21C—N21C—H22C	118.1 (18)
H51A—C51A—H53A	109.5	C4C—N3C—C2C	117.34 (13)
H52A—C51A—H53A	109.5	N3C—C4C—N41C	117.28 (15)
C5A—C6A—N1A	122.92 (14)	N3C—C4C—C5C	120.47 (14)
C5A—C6A—H6A	118.5	N41C—C4C—C5C	122.23 (16)
N1A—C6A—H6A	118.5	C4C—N41C—H41C	116.8 (14)
C2B—N1B—C6B	115.20 (13)	C4C—N41C—H42C	119.9 (14)
N1B—C2B—N3B	126.10 (14)	H41C—N41C—H42C	120 (2)
N1B—C2B—N21B	117.70 (14)	C6C—C5C—C4C	117.06 (16)
N3B—C2B—N21B	116.17 (14)	C6C—C5C—H5C	121.5
C2B—N21B—H21B	115.7 (13)	C4C—C5C—H5C	121.5
C2B—N21B—H22B	115.2 (13)	N1C—C6C—C5C	123.96 (15)
H21B—N21B—H22B	117.1 (18)	N1C—C6C—H6C	118.0
C4B—N3B—C2B	116.80 (13)	C5C—C6C—H6C	118.0
C6A—N1A—C2A—N3A	−0.5 (2)	C2B—N3B—C4B—N41B	178.86 (14)
C6A—N1A—C2A—S21A	179.01 (12)	C2B—N3B—C4B—C5B	−2.3 (2)
N1A—C2A—N3A—C4A	0.8 (2)	N3B—C4B—C5B—C6B	2.7 (2)
S21A—C2A—N3A—C4A	−178.68 (12)	N41B—C4B—C5B—C6B	−178.53 (15)
C2A—N3A—C4A—O41A	−179.86 (14)	C2B—N1B—C6B—C5B	−0.4 (2)
C2A—N3A—C4A—C5A	−0.7 (2)	C4B—C5B—C6B—N1B	−1.2 (2)
O41A—C4A—C5A—C6A	179.29 (15)	C6C—N1C—C2C—N3C	0.1 (2)
N3A—C4A—C5A—C6A	0.1 (2)	C6C—N1C—C2C—N21C	177.61 (14)
O41A—C4A—C5A—C51A	−0.8 (2)	N1C—C2C—N3C—C4C	0.1 (2)
N3A—C4A—C5A—C51A	−179.99 (14)	N21C—C2C—N3C—C4C	−177.40 (14)
C4A—C5A—C6A—N1A	0.2 (2)	C2C—N3C—C4C—N41C	−179.29 (14)
C51A—C5A—C6A—N1A	−179.72 (15)	C2C—N3C—C4C—C5C	−0.8 (2)
C2A—N1A—C6A—C5A	0.0 (2)	N3C—C4C—C5C—C6C	1.2 (2)
C6B—N1B—C2B—N3B	0.9 (2)	N41C—C4C—C5C—C6C	179.68 (16)
C6B—N1B—C2B—N21B	178.84 (14)	C2C—N1C—C6C—C5C	0.4 (2)
N1B—C2B—N3B—C4B	0.5 (2)	C4C—C5C—C6C—N1C	−1.0 (3)
N21B—C2B—N3B—C4B	−177.51 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N1B	0.87 (2)	1.95 (2)	2.8003 (19)	167 (2)
N3A—H3A···N1C	0.89 (1)	1.95 (2)	2.8352 (19)	175 (2)
N21B—H21B···S21A	0.88 (2)	2.85 (2)	3.6629 (16)	155 (2)
N21B—H22B···N3B^i	0.88 (2)	2.22 (2)	3.097 (2)	179 (2)
N41B—H41B···O41A^ii	0.89 (2)	2.04 (2)	2.8998 (19)	163 (2)
N41B—H42B···S21A^iii	0.88 (2)	2.87 (2)	3.5560 (16)	136 (2)
N21C—H21C···O41A	0.88 (2)	2.07 (2)	2.9381 (18)	171 (2)
N41C—H41C···N3C^iv	0.89 (2)	2.07 (2)	2.960 (2)	176 (2)
N41C—H42C···N21B^v	0.87 (2)	2.43 (2)	3.202 (2)	148 (2)

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) x+1, y, z+1; (iii) −x+1, −y+1, −z+2; (iv) −x, −y, −z; (v) −x+1, −y, −z+1.

5-Methyl-2-thiouracil–2,4-diaminopyrimidine–N,N-dimethylformamide (2/2/1) (II)

Crystal data

2C5H6N2OS·C3H7NO·2C4H6N4	F(000) = 1216
Mr = 577.71	Dx = 1.444 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 10.0743 (10) Å	Cell parameters from 21482 reflections
b = 14.383 (1) Å	θ = 3.3–26.2°
c = 18.647 (2) Å	µ = 0.25 mm^−1
β = 100.427 (8)°	T = 173 K
V = 2657.3 (4) Å^3	Block, colourless
Z = 4	0.28 × 0.26 × 0.11 mm

Data collection

STOE IPDS II two-circle diffractometer	4157 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.047
ω scans	θmax = 25.9°, θmin = 3.6°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −12→12
Tmin = 0.688, Tmax = 1.000	k = −17→17
11389 measured reflections	l = −21→22
4664 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0551P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.091	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.21 e Å^−3
4664 reflections	Δρmin = −0.29 e Å^−3
421 parameters	Absolute structure: Refined as an inversion twin.
128 restraints	Absolute structure parameter: 0.24 (10)

Special details

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

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1A	0.3216 (3)	0.1925 (2)	0.64680 (17)	0.0266 (7)
H1A	0.237 (3)	0.202 (3)	0.625 (2)	0.032*
C2A	0.4209 (4)	0.2179 (3)	0.6122 (2)	0.0256 (8)
S21A	0.39325 (9)	0.27994 (7)	0.53405 (5)	0.0296 (2)
N3A	0.5471 (3)	0.1914 (2)	0.64471 (16)	0.0244 (7)
H3A	0.613 (3)	0.210 (3)	0.624 (2)	0.029*
C4A	0.5804 (4)	0.1447 (3)	0.7112 (2)	0.0256 (9)
O41A	0.6992 (3)	0.1255 (2)	0.73535 (14)	0.0309 (6)
C5A	0.4691 (4)	0.1210 (3)	0.74581 (19)	0.0261 (8)
C51A	0.4957 (4)	0.0718 (3)	0.8178 (2)	0.0296 (9)
H51A	0.4101	0.0609	0.8344	0.044*
H51B	0.5546	0.1102	0.8537	0.044*
H51C	0.5399	0.0121	0.8125	0.044*
C6A	0.3438 (4)	0.1454 (3)	0.71190 (19)	0.0261 (8)
H6A	0.2688	0.1295	0.7338	0.031*
N1C	1.0462 (3)	0.2247 (2)	0.58547 (17)	0.0289 (7)
C2C	0.9303 (4)	0.2061 (3)	0.6080 (2)	0.0283 (9)
N21C	0.9373 (4)	0.1707 (3)	0.6755 (2)	0.0413 (10)
H21C	1.006 (4)	0.172 (3)	0.711 (2)	0.050*
H22C	0.866 (4)	0.164 (3)	0.696 (3)	0.050*
N3C	0.8036 (3)	0.2186 (2)	0.56911 (16)	0.0265 (7)
C4C	0.7966 (4)	0.2516 (3)	0.5011 (2)	0.0243 (8)
N41C	0.6727 (4)	0.2630 (3)	0.46025 (19)	0.0322 (8)
H41C	0.607 (4)	0.262 (3)	0.486 (2)	0.039*
H42C	0.670 (5)	0.295 (3)	0.4200 (18)	0.039*
C5C	0.9122 (4)	0.2726 (3)	0.4723 (2)	0.0303 (9)
H5C	0.9066	0.2951	0.4240	0.036*
C6C	1.0326 (4)	0.2591 (3)	0.5173 (2)	0.0313 (9)
H6C	1.1123	0.2749	0.4995	0.038*
N1B	0.7482 (3)	0.0814 (2)	0.17434 (17)	0.0276 (7)
H1B	0.836 (3)	0.095 (3)	0.192 (2)	0.033*
C2B	0.6497 (4)	0.1089 (3)	0.2094 (2)	0.0261 (8)
S21B	0.68032 (9)	0.16828 (7)	0.28776 (5)	0.0330 (3)
N3B	0.5213 (3)	0.0857 (2)	0.17654 (17)	0.0250 (7)
H3B	0.453 (3)	0.100 (3)	0.200 (2)	0.030*
C4B	0.4874 (4)	0.0408 (3)	0.1099 (2)	0.0268 (9)
O41B	0.3677 (3)	0.0234 (2)	0.08515 (15)	0.0376 (7)
C5B	0.5966 (4)	0.0146 (3)	0.0741 (2)	0.0270 (8)
C51B	0.5645 (5)	−0.0333 (3)	0.0021 (2)	0.0336 (10)
H51D	0.5162	0.0096	−0.0344	0.050*
H51E	0.5078	−0.0877	0.0061	0.050*
H51F	0.6485	−0.0533	−0.0129	0.050*
C6B	0.7230 (4)	0.0348 (3)	0.1089 (2)	0.0280 (9)
H6B	0.7972	0.0162	0.0873	0.034*
N1D	0.0259 (3)	0.1176 (2)	0.23786 (17)	0.0312 (8)
C2D	0.1417 (4)	0.1009 (3)	0.2147 (2)	0.0294 (9)
N21D	0.1343 (4)	0.0581 (4)	0.1501 (2)	0.0518 (11)
H21D	0.061 (4)	0.074 (4)	0.120 (3)	0.062*
H22D	0.207 (4)	0.053 (4)	0.129 (3)	0.062*
N3D	0.2671 (3)	0.1219 (2)	0.25040 (16)	0.0270 (7)
C4D	0.2746 (4)	0.1616 (3)	0.3159 (2)	0.0303 (9)
N41D	0.3980 (4)	0.1822 (3)	0.3536 (2)	0.0484 (11)
H41D	0.471 (4)	0.178 (4)	0.333 (3)	0.058*
H42D	0.404 (6)	0.202 (4)	0.3982 (18)	0.058*
C5D	0.1593 (4)	0.1808 (3)	0.3453 (2)	0.0303 (9)
H5D	0.1654	0.2088	0.3920	0.036*
C6D	0.0385 (4)	0.1578 (3)	0.3044 (2)	0.0287 (9)
H6D	−0.0411	0.1704	0.3234	0.034*
O11X	1.1290 (4)	0.1002 (2)	0.82647 (18)	0.0494 (8)
N2X	1.0104 (4)	0.0284 (2)	0.90302 (17)	0.0358 (8)
C1X	1.0216 (5)	0.0701 (3)	0.8407 (2)	0.0338 (12)	0.879 (7)
H1XA	0.9422	0.0773	0.8050	0.041*	0.879 (7)
C3X	1.1261 (6)	0.0079 (4)	0.9584 (3)	0.0490 (16)	0.879 (7)
H3XA	1.2087	0.0164	0.9383	0.073*	0.879 (7)
H3XB	1.1209	−0.0566	0.9746	0.073*	0.879 (7)
H3XC	1.1275	0.0499	0.9999	0.073*	0.879 (7)
C4X	0.8783 (6)	0.0015 (4)	0.9165 (3)	0.0538 (16)	0.879 (7)
H4XA	0.8102	0.0146	0.8731	0.081*	0.879 (7)
H4XB	0.8574	0.0369	0.9580	0.081*	0.879 (7)
H4XC	0.8781	−0.0651	0.9275	0.081*	0.879 (7)
C1X'	1.1258 (19)	0.049 (3)	0.8802 (17)	0.065 (9)	0.121 (7)
H1XB	1.2079	0.0228	0.9056	0.078*	0.121 (7)
C3X'	0.886 (2)	0.066 (3)	0.864 (2)	0.066 (12)	0.121 (7)
H3XD	0.8114	0.0446	0.8876	0.100*	0.121 (7)
H3XE	0.8901	0.1337	0.8653	0.100*	0.121 (7)
H3XF	0.8710	0.0439	0.8137	0.100*	0.121 (7)
C4X'	1.011 (4)	−0.019 (3)	0.9719 (16)	0.066 (13)	0.121 (7)
H4XD	0.9183	−0.0279	0.9795	0.099*	0.121 (7)
H4XE	1.0550	−0.0799	0.9709	0.099*	0.121 (7)
H4XF	1.0612	0.0182	1.0119	0.099*	0.121 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0252 (18)	0.0313 (17)	0.0232 (17)	0.0029 (15)	0.0044 (13)	0.0020 (14)
C2A	0.028 (2)	0.0252 (18)	0.0243 (18)	0.0030 (16)	0.0058 (16)	−0.0037 (15)
S21A	0.0274 (5)	0.0385 (5)	0.0233 (5)	0.0057 (4)	0.0052 (4)	0.0057 (4)
N3A	0.0216 (17)	0.0308 (17)	0.0215 (16)	0.0014 (14)	0.0057 (13)	0.0015 (13)
C4A	0.031 (2)	0.0240 (19)	0.0212 (18)	0.0028 (17)	0.0019 (17)	−0.0030 (15)
O41A	0.0234 (14)	0.0428 (17)	0.0259 (13)	0.0044 (12)	0.0026 (11)	0.0047 (11)
C5A	0.028 (2)	0.0278 (19)	0.0224 (18)	0.0012 (16)	0.0050 (17)	−0.0035 (15)
C51A	0.032 (2)	0.036 (2)	0.0218 (18)	−0.0005 (18)	0.0057 (17)	0.0012 (16)
C6A	0.030 (2)	0.0271 (18)	0.0217 (18)	0.0026 (16)	0.0066 (16)	−0.0010 (15)
N1C	0.0267 (18)	0.0376 (19)	0.0226 (16)	−0.0013 (15)	0.0053 (14)	−0.0012 (13)
C2C	0.029 (2)	0.032 (2)	0.0232 (19)	0.0000 (17)	0.0022 (17)	−0.0010 (15)
N21C	0.027 (2)	0.070 (3)	0.0243 (19)	0.0012 (19)	−0.0012 (16)	0.0141 (17)
N3C	0.0253 (17)	0.0316 (17)	0.0209 (15)	−0.0003 (14)	−0.0002 (14)	0.0035 (13)
C4C	0.030 (2)	0.0217 (18)	0.0215 (18)	−0.0018 (16)	0.0047 (15)	−0.0037 (14)
N41C	0.028 (2)	0.044 (2)	0.0241 (17)	0.0018 (16)	0.0029 (14)	0.0093 (15)
C5C	0.033 (2)	0.036 (2)	0.023 (2)	0.0005 (17)	0.0072 (18)	0.0016 (15)
C6C	0.029 (2)	0.037 (2)	0.029 (2)	−0.0012 (19)	0.0096 (19)	−0.0034 (17)
N1B	0.0246 (18)	0.0319 (17)	0.0267 (18)	−0.0024 (15)	0.0059 (14)	0.0008 (14)
C2B	0.028 (2)	0.0275 (19)	0.0232 (18)	−0.0002 (17)	0.0064 (16)	0.0024 (15)
S21B	0.0266 (5)	0.0436 (6)	0.0294 (5)	−0.0037 (5)	0.0063 (4)	−0.0107 (4)
N3B	0.0214 (16)	0.0305 (17)	0.0235 (17)	−0.0023 (13)	0.0052 (14)	−0.0002 (12)
C4B	0.028 (2)	0.030 (2)	0.0209 (18)	0.0020 (16)	0.0021 (17)	0.0037 (15)
O41B	0.0293 (16)	0.0555 (19)	0.0270 (14)	−0.0038 (15)	0.0024 (12)	−0.0057 (13)
C5B	0.033 (2)	0.0279 (19)	0.0209 (18)	−0.0008 (17)	0.0062 (16)	0.0022 (15)
C51B	0.041 (3)	0.036 (2)	0.025 (2)	0.0004 (19)	0.0094 (19)	−0.0004 (17)
C6B	0.031 (2)	0.029 (2)	0.026 (2)	0.0006 (16)	0.0100 (17)	0.0007 (15)
N1D	0.0277 (19)	0.042 (2)	0.0241 (16)	−0.0005 (16)	0.0044 (14)	−0.0013 (14)
C2D	0.027 (2)	0.039 (2)	0.0222 (19)	0.0015 (18)	0.0047 (17)	−0.0002 (16)
N21D	0.027 (2)	0.099 (3)	0.030 (2)	−0.003 (2)	0.0063 (16)	−0.025 (2)
N3D	0.0237 (17)	0.0340 (18)	0.0231 (16)	0.0025 (14)	0.0037 (13)	0.0000 (13)
C4D	0.030 (2)	0.035 (2)	0.024 (2)	−0.0011 (18)	0.0005 (17)	−0.0011 (16)
N41D	0.029 (2)	0.086 (3)	0.030 (2)	−0.004 (2)	0.0039 (17)	−0.024 (2)
C5D	0.030 (2)	0.040 (2)	0.0216 (19)	−0.0012 (18)	0.0066 (18)	−0.0024 (15)
C6D	0.028 (2)	0.033 (2)	0.026 (2)	0.0036 (17)	0.0056 (17)	0.0005 (16)
O11X	0.061 (2)	0.0503 (18)	0.0429 (18)	−0.0136 (17)	0.0251 (16)	−0.0031 (14)
N2X	0.043 (2)	0.0378 (18)	0.0269 (17)	−0.0040 (16)	0.0082 (15)	−0.0022 (14)
C1X	0.046 (3)	0.033 (2)	0.020 (2)	−0.005 (2)	0.0013 (19)	−0.0027 (18)
C3X	0.067 (4)	0.044 (3)	0.030 (3)	−0.001 (3)	−0.010 (3)	0.009 (2)
C4X	0.055 (3)	0.057 (3)	0.057 (3)	−0.016 (3)	0.029 (3)	−0.015 (3)
C1X'	0.077 (16)	0.07 (2)	0.058 (19)	−0.004 (19)	0.031 (17)	0.007 (15)
C3X'	0.071 (18)	0.05 (2)	0.06 (3)	0.01 (2)	−0.01 (2)	0.01 (2)
C4X'	0.07 (3)	0.10 (3)	0.022 (16)	−0.01 (2)	−0.003 (16)	0.011 (16)

Geometric parameters (Å, º)

N1A—C2A	1.336 (5)	C51B—H51D	0.9800
N1A—C6A	1.372 (5)	C51B—H51E	0.9800
N1A—H1A	0.89 (3)	C51B—H51F	0.9800
C2A—N3A	1.360 (5)	C6B—H6B	0.9500
C2A—S21A	1.688 (4)	N1D—C2D	1.337 (5)
N3A—C4A	1.396 (5)	N1D—C6D	1.354 (5)
N3A—H3A	0.88 (3)	C2D—N21D	1.343 (5)
C4A—O41A	1.231 (5)	C2D—N3D	1.352 (5)
C4A—C5A	1.433 (6)	N21D—H21D	0.87 (3)
C5A—C6A	1.351 (5)	N21D—H22D	0.89 (3)
C5A—C51A	1.499 (5)	N3D—C4D	1.338 (5)
C51A—H51A	0.9800	C4D—N41D	1.345 (6)
C51A—H51B	0.9800	C4D—C5D	1.399 (6)
C51A—H51C	0.9800	N41D—H41D	0.89 (3)
C6A—H6A	0.9500	N41D—H42D	0.87 (3)
N1C—C2C	1.339 (6)	C5D—C6D	1.355 (6)
N1C—C6C	1.348 (5)	C5D—H5D	0.9500
C2C—N21C	1.346 (5)	C6D—H6D	0.9500
C2C—N3C	1.361 (5)	O11X—C1X	1.238 (6)
N21C—H21C	0.87 (3)	O11X—C1X'	1.253 (14)
N21C—H22C	0.88 (3)	N2X—C1X	1.330 (5)
N3C—C4C	1.345 (5)	N2X—C1X'	1.340 (13)
C4C—N41C	1.349 (5)	N2X—C3X'	1.433 (13)
C4C—C5C	1.400 (6)	N2X—C3X	1.441 (5)
N41C—H41C	0.88 (3)	N2X—C4X	1.451 (6)
N41C—H42C	0.88 (3)	N2X—C4X'	1.455 (18)
C5C—C6C	1.357 (6)	C1X—H1XA	0.9500
C5C—H5C	0.9500	C3X—H3XA	0.9800
C6C—H6C	0.9500	C3X—H3XB	0.9800
N1B—C2B	1.343 (5)	C3X—H3XC	0.9800
N1B—C6B	1.376 (5)	C4X—H4XA	0.9800
N1B—H1B	0.90 (2)	C4X—H4XB	0.9800
C2B—N3B	1.368 (5)	C4X—H4XC	0.9800
C2B—S21B	1.672 (4)	C1X'—H1XB	0.9500
N3B—C4B	1.387 (5)	C3X'—H3XD	0.9800
N3B—H3B	0.90 (2)	C3X'—H3XE	0.9800
C4B—O41B	1.236 (5)	C3X'—H3XF	0.9800
C4B—C5B	1.437 (6)	C4X'—H4XD	0.9800
C5B—C6B	1.351 (6)	C4X'—H4XE	0.9800
C5B—C51B	1.492 (5)	C4X'—H4XF	0.9800
C2A—N1A—C6A	123.1 (3)	C5B—C51B—H51F	109.5
C2A—N1A—H1A	119 (3)	H51D—C51B—H51F	109.5
C6A—N1A—H1A	118 (3)	H51E—C51B—H51F	109.5
N1A—C2A—N3A	115.4 (3)	C5B—C6B—N1B	122.5 (4)
N1A—C2A—S21A	122.7 (3)	C5B—C6B—H6B	118.7
N3A—C2A—S21A	121.8 (3)	N1B—C6B—H6B	118.7
C2A—N3A—C4A	125.8 (3)	C2D—N1D—C6D	115.5 (3)
C2A—N3A—H3A	116 (3)	N1D—C2D—N21D	117.5 (4)
C4A—N3A—H3A	118 (3)	N1D—C2D—N3D	126.4 (4)
O41A—C4A—N3A	119.6 (4)	N21D—C2D—N3D	116.1 (4)
O41A—C4A—C5A	124.7 (3)	C2D—N21D—H21D	112 (4)
N3A—C4A—C5A	115.6 (3)	C2D—N21D—H22D	121 (4)
C6A—C5A—C4A	117.9 (3)	H21D—N21D—H22D	114 (5)
C6A—C5A—C51A	122.8 (4)	C4D—N3D—C2D	116.0 (3)
C4A—C5A—C51A	119.2 (3)	N3D—C4D—N41D	117.7 (4)
C5A—C51A—H51A	109.5	N3D—C4D—C5D	121.9 (4)
C5A—C51A—H51B	109.5	N41D—C4D—C5D	120.4 (4)
H51A—C51A—H51B	109.5	C4D—N41D—H41D	121 (4)
C5A—C51A—H51C	109.5	C4D—N41D—H42D	118 (4)
H51A—C51A—H51C	109.5	H41D—N41D—H42D	121 (5)
H51B—C51A—H51C	109.5	C6D—C5D—C4D	117.1 (4)
C5A—C6A—N1A	122.1 (4)	C6D—C5D—H5D	121.4
C5A—C6A—H6A	119.0	C4D—C5D—H5D	121.4
N1A—C6A—H6A	119.0	N1D—C6D—C5D	123.1 (4)
C2C—N1C—C6C	115.1 (3)	N1D—C6D—H6D	118.5
N1C—C2C—N21C	117.9 (4)	C5D—C6D—H6D	118.5
N1C—C2C—N3C	126.4 (3)	C1X'—N2X—C3X'	119.4 (16)
N21C—C2C—N3C	115.7 (4)	C1X—N2X—C3X	122.2 (4)
C2C—N21C—H21C	127 (4)	C1X—N2X—C4X	119.8 (4)
C2C—N21C—H22C	122 (3)	C3X—N2X—C4X	118.0 (4)
H21C—N21C—H22C	106 (5)	C1X'—N2X—C4X'	121.0 (16)
C4C—N3C—C2C	115.7 (3)	C3X'—N2X—C4X'	119.0 (18)
N3C—C4C—N41C	117.4 (4)	O11X—C1X—N2X	124.1 (4)
N3C—C4C—C5C	122.1 (4)	O11X—C1X—H1XA	117.9
N41C—C4C—C5C	120.4 (4)	N2X—C1X—H1XA	117.9
C4C—N41C—H41C	114 (3)	N2X—C3X—H3XA	109.5
C4C—N41C—H42C	115 (3)	N2X—C3X—H3XB	109.5
H41C—N41C—H42C	124 (5)	H3XA—C3X—H3XB	109.5
C6C—C5C—C4C	116.4 (4)	N2X—C3X—H3XC	109.5
C6C—C5C—H5C	121.8	H3XA—C3X—H3XC	109.5
C4C—C5C—H5C	121.8	H3XB—C3X—H3XC	109.5
N1C—C6C—C5C	124.2 (4)	N2X—C4X—H4XA	109.5
N1C—C6C—H6C	117.9	N2X—C4X—H4XB	109.5
C5C—C6C—H6C	117.9	H4XA—C4X—H4XB	109.5
C2B—N1B—C6B	122.8 (3)	N2X—C4X—H4XC	109.5
C2B—N1B—H1B	121 (3)	H4XA—C4X—H4XC	109.5
C6B—N1B—H1B	117 (3)	H4XB—C4X—H4XC	109.5
N1B—C2B—N3B	115.6 (3)	O11X—C1X'—N2X	122.1 (15)
N1B—C2B—S21B	122.7 (3)	O11X—C1X'—H1XB	118.9
N3B—C2B—S21B	121.8 (3)	N2X—C1X'—H1XB	118.9
C2B—N3B—C4B	125.1 (3)	N2X—C3X'—H3XD	109.5
C2B—N3B—H3B	118 (3)	N2X—C3X'—H3XE	109.5
C4B—N3B—H3B	117 (3)	H3XD—C3X'—H3XE	109.5
O41B—C4B—N3B	119.7 (4)	N2X—C3X'—H3XF	109.5
O41B—C4B—C5B	123.4 (4)	H3XD—C3X'—H3XF	109.5
N3B—C4B—C5B	116.9 (4)	H3XE—C3X'—H3XF	109.5
C6B—C5B—C4B	117.0 (3)	N2X—C4X'—H4XD	109.5
C6B—C5B—C51B	124.3 (4)	N2X—C4X'—H4XE	109.5
C4B—C5B—C51B	118.7 (4)	H4XD—C4X'—H4XE	109.5
C5B—C51B—H51D	109.5	N2X—C4X'—H4XF	109.5
C5B—C51B—H51E	109.5	H4XD—C4X'—H4XF	109.5
H51D—C51B—H51E	109.5	H4XE—C4X'—H4XF	109.5
C6A—N1A—C2A—N3A	2.0 (5)	N1B—C2B—N3B—C4B	−3.0 (5)
C6A—N1A—C2A—S21A	−177.2 (3)	S21B—C2B—N3B—C4B	176.6 (3)
N1A—C2A—N3A—C4A	−3.0 (5)	C2B—N3B—C4B—O41B	−179.7 (3)
S21A—C2A—N3A—C4A	176.3 (3)	C2B—N3B—C4B—C5B	1.9 (6)
C2A—N3A—C4A—O41A	−179.1 (3)	O41B—C4B—C5B—C6B	−177.5 (4)
C2A—N3A—C4A—C5A	2.0 (5)	N3B—C4B—C5B—C6B	0.9 (5)
O41A—C4A—C5A—C6A	−178.8 (4)	O41B—C4B—C5B—C51B	2.1 (6)
N3A—C4A—C5A—C6A	0.1 (5)	N3B—C4B—C5B—C51B	−179.6 (3)
O41A—C4A—C5A—C51A	1.8 (6)	C4B—C5B—C6B—N1B	−2.4 (5)
N3A—C4A—C5A—C51A	−179.3 (3)	C51B—C5B—C6B—N1B	178.1 (3)
C4A—C5A—C6A—N1A	−0.9 (5)	C2B—N1B—C6B—C5B	1.2 (6)
C51A—C5A—C6A—N1A	178.4 (3)	C6D—N1D—C2D—N21D	177.7 (4)
C2A—N1A—C6A—C5A	−0.2 (6)	C6D—N1D—C2D—N3D	−1.6 (6)
C6C—N1C—C2C—N21C	179.4 (4)	N1D—C2D—N3D—C4D	1.5 (6)
C6C—N1C—C2C—N3C	0.0 (6)	N21D—C2D—N3D—C4D	−177.8 (4)
N1C—C2C—N3C—C4C	1.1 (6)	C2D—N3D—C4D—N41D	178.9 (4)
N21C—C2C—N3C—C4C	−178.4 (4)	C2D—N3D—C4D—C5D	−0.5 (6)
C2C—N3C—C4C—N41C	178.6 (3)	N3D—C4D—C5D—C6D	−0.3 (6)
C2C—N3C—C4C—C5C	−0.5 (5)	N41D—C4D—C5D—C6D	−179.6 (4)
N3C—C4C—C5C—C6C	−1.0 (6)	C2D—N1D—C6D—C5D	0.7 (6)
N41C—C4C—C5C—C6C	180.0 (4)	C4D—C5D—C6D—N1D	0.2 (6)
C2C—N1C—C6C—C5C	−1.7 (6)	C3X—N2X—C1X—O11X	−4.8 (7)
C4C—C5C—C6C—N1C	2.1 (6)	C4X—N2X—C1X—O11X	175.6 (4)
C6B—N1B—C2B—N3B	1.4 (5)	C3X'—N2X—C1X'—O11X	1 (6)
C6B—N1B—C2B—S21B	−178.2 (3)	C4X'—N2X—C1X'—O11X	−170 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N1C^i	0.89 (3)	1.95 (3)	2.841 (5)	175 (4)
N3A—H3A···N3C	0.88 (3)	2.33 (3)	3.184 (5)	165 (4)
N1B—H1B···N1D^ii	0.90 (2)	1.98 (3)	2.881 (5)	176 (4)
N3B—H3B···N3D	0.90 (2)	2.27 (3)	3.163 (5)	173 (4)
N21C—H21C···O11X	0.87 (3)	2.51 (4)	3.274 (5)	148 (4)
N21C—H22C···O41A	0.88 (3)	2.03 (3)	2.897 (5)	170 (5)
N41C—H41C···S21A	0.88 (3)	2.49 (3)	3.359 (4)	167 (4)
N41C—H42C···O11X^iii	0.88 (3)	2.28 (3)	3.145 (5)	167 (4)
N21D—H22D···O41B	0.89 (3)	2.00 (3)	2.876 (5)	172 (5)
N41D—H41D···S21B	0.89 (3)	2.41 (3)	3.302 (5)	175 (5)
C6A—H6A···O11X^i	0.95	2.45	3.368 (5)	161

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x−1/2, −y+1/2, z−1/2.

5-Methyl-2-thiouracil–2,4-diamino-6-phenyl-1,3,5-triazine–N,N-dimethylformamide (2/2/1) (III)

Crystal data

2C9H9N5·2C5H6N2OS·C3H7NO	F(000) = 1536
Mr = 731.87	Dx = 1.362 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.1237 (13) Å	Cell parameters from 10197 reflections
b = 19.5259 (14) Å	θ = 3.4–26.1°
c = 16.7313 (16) Å	µ = 0.21 mm^−1
β = 100.900 (8)°	T = 173 K
V = 3568.5 (6) Å^3	Block, colourless
Z = 4	0.29 × 0.21 × 0.14 mm

Data collection

STOE IPDS II two-circle diffractometer	4005 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.122
ω scans	θmax = 25.9°, θmin = 3.4°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −13→13
Tmin = 0.707, Tmax = 1.000	k = −21→23
28366 measured reflections	l = −20→20
6888 independent reflections

Refinement

Refinement on F^2	12 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.0242P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.89	(Δ/σ)max < 0.001
6888 reflections	Δρmax = 0.27 e Å^−3
500 parameters	Δρmin = −0.25 e Å^−3

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1A	0.7240 (2)	0.33781 (12)	0.35861 (13)	0.0238 (5)
H1A	0.695 (3)	0.3342 (16)	0.3080 (11)	0.029*
C2A	0.7848 (3)	0.28178 (14)	0.39106 (16)	0.0233 (6)
S21A	0.78557 (8)	0.20860 (4)	0.33951 (4)	0.0321 (2)
N3A	0.8457 (2)	0.28922 (12)	0.46960 (13)	0.0241 (5)
H3A	0.891 (3)	0.2545 (12)	0.4926 (17)	0.029*
C4A	0.8553 (3)	0.34968 (14)	0.51513 (16)	0.0250 (6)
O41A	0.9210 (2)	0.35168 (11)	0.58258 (11)	0.0335 (5)
C5A	0.7859 (3)	0.40710 (14)	0.47647 (16)	0.0243 (6)
C51A	0.7929 (3)	0.47369 (16)	0.52174 (18)	0.0357 (8)
H51A	0.8758	0.4925	0.5276	0.054*
H52A	0.7734	0.4660	0.5757	0.054*
H53A	0.7340	0.5061	0.4915	0.054*
C6A	0.7228 (3)	0.39836 (15)	0.39988 (16)	0.0255 (6)
H6A	0.6759	0.4355	0.3737	0.031*
N1C	1.1528 (2)	0.14570 (11)	0.68091 (13)	0.0234 (5)
C2C	1.0923 (3)	0.19154 (14)	0.62862 (16)	0.0227 (6)
N21C	1.1082 (3)	0.25761 (12)	0.64879 (15)	0.0333 (7)
H21C	1.143 (3)	0.2653 (17)	0.6986 (12)	0.040*
H22C	1.054 (3)	0.2875 (14)	0.6270 (18)	0.040*
N3C	1.0171 (2)	0.17618 (11)	0.55747 (12)	0.0223 (5)
C4C	1.0093 (3)	0.10863 (14)	0.54062 (15)	0.0222 (6)
N41C	0.9375 (2)	0.08944 (13)	0.47015 (14)	0.0301 (6)
H41C	0.905 (3)	0.1223 (13)	0.4371 (16)	0.036*
H42C	0.943 (3)	0.0461 (10)	0.4540 (18)	0.036*
N5C	1.0682 (2)	0.05846 (11)	0.58753 (12)	0.0222 (5)
C6C	1.1378 (2)	0.08062 (14)	0.65682 (15)	0.0204 (6)
C7C	1.2063 (3)	0.02851 (14)	0.71324 (15)	0.0222 (6)
C8C	1.3264 (3)	0.04220 (15)	0.75211 (16)	0.0261 (7)
H8C	1.3655	0.0834	0.7409	0.031*
C9C	1.3883 (3)	−0.00480 (17)	0.80715 (17)	0.0343 (8)
H9C	1.4711	0.0032	0.8321	0.041*
C10C	1.3289 (3)	−0.06353 (16)	0.82574 (18)	0.0405 (9)
H10C	1.3709	−0.0950	0.8645	0.049*
C11C	1.2102 (3)	−0.07673 (16)	0.78890 (17)	0.0358 (8)
H11C	1.1702	−0.1168	0.8027	0.043*
C12C	1.1484 (3)	−0.03104 (14)	0.73093 (16)	0.0268 (7)
H12C	1.0672	−0.0407	0.7038	0.032*
N1B	0.3071 (2)	0.67042 (13)	0.09829 (15)	0.0321 (6)
H1B	0.263 (3)	0.6411 (14)	0.0672 (17)	0.039*
C2B	0.3440 (3)	0.65385 (16)	0.17798 (19)	0.0326 (7)
S21B	0.31177 (9)	0.57761 (4)	0.21378 (5)	0.0461 (3)
N3B	0.4072 (2)	0.70320 (13)	0.22484 (15)	0.0315 (6)
H3B	0.433 (3)	0.6925 (17)	0.2763 (12)	0.038*
C4B	0.4289 (3)	0.76923 (16)	0.20038 (19)	0.0325 (7)
O41B	0.4836 (2)	0.81099 (11)	0.24972 (14)	0.0428 (6)
C5B	0.3828 (3)	0.78429 (16)	0.11545 (18)	0.0313 (7)
C51B	0.3956 (3)	0.85587 (17)	0.0853 (2)	0.0394 (8)
H51B	0.3665	0.8574	0.0262	0.059*
H52B	0.4819	0.8696	0.0979	0.059*
H53B	0.3469	0.8873	0.1119	0.059*
C6B	0.3249 (3)	0.73434 (16)	0.06820 (19)	0.0331 (7)
H6B	0.2953	0.7434	0.0121	0.040*
N1D	0.5502 (3)	0.72591 (13)	0.53770 (15)	0.0376 (7)
C2D	0.5200 (3)	0.72647 (16)	0.45575 (19)	0.0397 (9)
N21D	0.5180 (4)	0.78706 (16)	0.41994 (18)	0.0591 (10)
H21D	0.546 (4)	0.8241 (15)	0.448 (2)	0.071*
H22D	0.513 (4)	0.788 (2)	0.3662 (12)	0.071*
N3D	0.4944 (3)	0.67046 (13)	0.40835 (15)	0.0355 (7)
C4D	0.5034 (3)	0.61157 (16)	0.45022 (18)	0.0317 (7)
N41D	0.4798 (3)	0.55376 (14)	0.40628 (16)	0.0391 (7)
H41D	0.451 (3)	0.5580 (18)	0.3540 (12)	0.047*
H42D	0.474 (3)	0.5131 (12)	0.4289 (19)	0.047*
N5D	0.5378 (2)	0.60452 (13)	0.53214 (14)	0.0296 (6)
C6D	0.5584 (3)	0.66449 (15)	0.57198 (17)	0.0279 (7)
C7D	0.5986 (3)	0.66376 (15)	0.66242 (17)	0.0285 (7)
C8D	0.6169 (3)	0.72528 (16)	0.70468 (19)	0.0368 (8)
H8D	0.5980	0.7671	0.6761	0.044*
C9D	0.6622 (3)	0.72679 (18)	0.7876 (2)	0.0434 (9)
H9D	0.6743	0.7694	0.8155	0.052*
C10D	0.6899 (3)	0.66622 (19)	0.82988 (19)	0.0404 (8)
H10D	0.7235	0.6670	0.8865	0.048*
C11D	0.6682 (3)	0.60473 (18)	0.78925 (19)	0.0418 (9)
H11D	0.6832	0.5629	0.8185	0.050*
C12D	0.6247 (3)	0.60345 (17)	0.70574 (19)	0.0379 (8)
H12D	0.6127	0.5608	0.6781	0.045*
C1X	0.1583 (3)	0.52923 (16)	−0.03270 (18)	0.0315 (7)
H1X	0.2288	0.5039	−0.0087	0.038*
O11X	0.1548 (2)	0.59035 (11)	−0.01475 (13)	0.0381 (6)
N2X	0.0709 (2)	0.49640 (13)	−0.08292 (15)	0.0326 (6)
C3X	−0.0384 (3)	0.53253 (18)	−0.1233 (2)	0.0391 (8)
H3X1	−0.0574	0.5694	−0.0880	0.059*
H3X2	−0.1073	0.5005	−0.1344	0.059*
H3X3	−0.0239	0.5520	−0.1746	0.059*
C4X	0.0826 (4)	0.42428 (18)	−0.1020 (2)	0.0479 (9)
H4X1	0.0890	0.4195	−0.1593	0.072*
H4X2	0.0104	0.3994	−0.0920	0.072*
H4X3	0.1562	0.4054	−0.0675	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0297 (14)	0.0224 (13)	0.0154 (11)	−0.0009 (11)	−0.0061 (10)	0.0013 (10)
C2A	0.0247 (15)	0.0212 (15)	0.0217 (14)	−0.0028 (12)	−0.0019 (11)	0.0020 (11)
S21A	0.0474 (5)	0.0169 (4)	0.0247 (4)	0.0006 (3)	−0.0120 (3)	−0.0006 (3)
N3A	0.0296 (14)	0.0180 (12)	0.0208 (12)	−0.0007 (11)	−0.0050 (10)	0.0014 (10)
C4A	0.0279 (16)	0.0243 (16)	0.0222 (14)	−0.0011 (13)	0.0030 (12)	0.0020 (12)
O41A	0.0441 (13)	0.0278 (12)	0.0217 (10)	0.0052 (10)	−0.0114 (9)	−0.0017 (8)
C5A	0.0246 (15)	0.0234 (15)	0.0245 (14)	0.0023 (12)	0.0036 (11)	0.0023 (11)
C51A	0.045 (2)	0.0264 (16)	0.0295 (16)	0.0080 (14)	−0.0074 (14)	−0.0041 (13)
C6A	0.0262 (16)	0.0229 (16)	0.0255 (14)	0.0020 (12)	−0.0005 (12)	0.0047 (12)
N1C	0.0273 (13)	0.0189 (12)	0.0202 (11)	0.0003 (10)	−0.0055 (10)	−0.0006 (9)
C2C	0.0260 (15)	0.0192 (15)	0.0211 (13)	−0.0010 (12)	−0.0006 (11)	0.0017 (11)
N21C	0.0485 (17)	0.0169 (13)	0.0252 (13)	0.0025 (12)	−0.0170 (12)	−0.0027 (10)
N3C	0.0315 (13)	0.0164 (12)	0.0162 (11)	0.0007 (10)	−0.0025 (9)	−0.0023 (9)
C4C	0.0270 (16)	0.0206 (14)	0.0180 (13)	−0.0010 (12)	0.0019 (11)	−0.0029 (11)
N41C	0.0439 (16)	0.0169 (13)	0.0225 (13)	0.0020 (11)	−0.0117 (11)	−0.0026 (10)
N5C	0.0291 (13)	0.0179 (12)	0.0169 (11)	−0.0001 (10)	−0.0024 (10)	−0.0017 (9)
C6C	0.0207 (14)	0.0194 (14)	0.0198 (13)	0.0018 (12)	0.0003 (11)	0.0000 (11)
C7C	0.0287 (16)	0.0183 (14)	0.0178 (13)	0.0070 (12)	−0.0006 (11)	−0.0029 (11)
C8C	0.0276 (16)	0.0242 (15)	0.0246 (14)	0.0043 (12)	0.0002 (12)	−0.0052 (11)
C9C	0.0332 (18)	0.0356 (19)	0.0289 (16)	0.0140 (14)	−0.0070 (13)	−0.0060 (13)
C10C	0.063 (2)	0.0298 (18)	0.0232 (15)	0.0222 (16)	−0.0057 (15)	0.0008 (13)
C11C	0.059 (2)	0.0231 (16)	0.0225 (15)	0.0035 (16)	0.0011 (15)	−0.0006 (12)
C12C	0.0357 (17)	0.0192 (15)	0.0228 (14)	0.0023 (13)	−0.0013 (12)	−0.0013 (11)
N1B	0.0322 (15)	0.0275 (15)	0.0337 (14)	−0.0025 (11)	−0.0015 (11)	−0.0036 (11)
C2B	0.0266 (17)	0.0264 (17)	0.0423 (18)	−0.0010 (13)	0.0001 (14)	0.0012 (14)
S21B	0.0513 (6)	0.0265 (4)	0.0512 (5)	−0.0139 (4)	−0.0142 (4)	0.0101 (4)
N3B	0.0318 (15)	0.0236 (14)	0.0355 (14)	−0.0067 (11)	−0.0028 (11)	0.0026 (11)
C4B	0.0319 (18)	0.0237 (16)	0.0419 (18)	−0.0013 (13)	0.0070 (14)	0.0037 (14)
O41B	0.0526 (15)	0.0276 (12)	0.0449 (13)	−0.0122 (11)	0.0007 (11)	0.0006 (10)
C5B	0.0320 (17)	0.0285 (17)	0.0349 (16)	0.0020 (14)	0.0104 (13)	0.0025 (14)
C51B	0.048 (2)	0.0267 (17)	0.0449 (19)	0.0031 (15)	0.0115 (16)	0.0081 (14)
C6B	0.0339 (18)	0.0323 (17)	0.0341 (17)	0.0063 (14)	0.0088 (14)	0.0023 (14)
N1D	0.0449 (17)	0.0249 (14)	0.0375 (15)	−0.0037 (12)	−0.0059 (12)	−0.0006 (11)
C2D	0.046 (2)	0.0273 (18)	0.0384 (18)	−0.0066 (15)	−0.0103 (15)	0.0063 (14)
N21D	0.100 (3)	0.0249 (16)	0.0395 (17)	−0.0150 (17)	−0.0194 (18)	0.0039 (14)
N3D	0.0451 (17)	0.0230 (14)	0.0328 (14)	−0.0095 (12)	−0.0064 (12)	0.0051 (11)
C4D	0.0312 (18)	0.0260 (16)	0.0356 (17)	−0.0051 (13)	0.0007 (14)	0.0023 (14)
N41D	0.060 (2)	0.0249 (14)	0.0278 (14)	−0.0099 (13)	−0.0023 (13)	0.0027 (11)
N5D	0.0298 (14)	0.0255 (14)	0.0319 (13)	−0.0049 (11)	0.0021 (11)	0.0016 (11)
C6D	0.0214 (15)	0.0262 (16)	0.0345 (16)	−0.0026 (12)	0.0011 (12)	0.0001 (13)
C7D	0.0272 (16)	0.0256 (16)	0.0330 (16)	−0.0046 (13)	0.0066 (13)	−0.0022 (13)
C8D	0.047 (2)	0.0263 (17)	0.0395 (18)	−0.0005 (15)	0.0143 (15)	0.0017 (13)
C9D	0.058 (2)	0.038 (2)	0.0378 (19)	−0.0105 (17)	0.0173 (17)	−0.0108 (15)
C10D	0.043 (2)	0.051 (2)	0.0295 (17)	−0.0028 (17)	0.0126 (15)	−0.0041 (15)
C11D	0.050 (2)	0.0374 (19)	0.0337 (18)	0.0032 (16)	−0.0023 (15)	0.0048 (15)
C12D	0.043 (2)	0.0272 (17)	0.0386 (18)	0.0045 (15)	−0.0048 (15)	−0.0011 (14)
C1X	0.0332 (18)	0.0279 (17)	0.0335 (16)	0.0003 (14)	0.0064 (13)	0.0022 (13)
O11X	0.0457 (14)	0.0250 (12)	0.0397 (12)	−0.0003 (10)	−0.0022 (10)	−0.0018 (9)
N2X	0.0363 (16)	0.0251 (14)	0.0371 (14)	−0.0016 (11)	0.0089 (12)	−0.0017 (11)
C3X	0.0358 (19)	0.0383 (19)	0.0406 (18)	−0.0042 (15)	0.0005 (15)	−0.0012 (15)
C4X	0.067 (3)	0.0295 (19)	0.052 (2)	−0.0021 (18)	0.0225 (18)	−0.0119 (16)

Geometric parameters (Å, º)

N1A—C2A	1.345 (3)	N3B—H3B	0.880 (18)
N1A—C6A	1.370 (4)	C4B—O41B	1.236 (4)
N1A—H1A	0.849 (17)	C4B—C5B	1.447 (4)
C2A—N3A	1.368 (3)	C5B—C6B	1.341 (4)
C2A—S21A	1.670 (3)	C5B—C51B	1.502 (4)
N3A—C4A	1.398 (4)	C51B—H51B	0.9800
N3A—H3A	0.890 (18)	C51B—H52B	0.9800
C4A—O41A	1.224 (3)	C51B—H53B	0.9800
C4A—C5A	1.443 (4)	C6B—H6B	0.9500
C5A—C6A	1.351 (4)	N1D—C6D	1.325 (4)
C5A—C51A	1.499 (4)	N1D—C2D	1.349 (4)
C51A—H51A	0.9800	C2D—N21D	1.324 (4)
C51A—H52A	0.9800	C2D—N3D	1.349 (4)
C51A—H53A	0.9800	N21D—H21D	0.886 (19)
C6A—H6A	0.9500	N21D—H22D	0.891 (19)
N1C—C6C	1.334 (3)	N3D—C4D	1.340 (4)
N1C—C2C	1.340 (3)	C4D—N41D	1.345 (4)
C2C—N21C	1.337 (4)	C4D—N5D	1.359 (4)
C2C—N3C	1.353 (3)	N41D—H41D	0.877 (18)
N21C—H21C	0.864 (18)	N41D—H42D	0.887 (18)
N21C—H22C	0.870 (18)	N5D—C6D	1.345 (4)
N3C—C4C	1.348 (3)	C6D—C7D	1.495 (4)
C4C—N5C	1.345 (3)	C7D—C12D	1.384 (4)
C4C—N41C	1.346 (3)	C7D—C8D	1.389 (4)
N41C—H41C	0.879 (18)	C8D—C9D	1.384 (5)
N41C—H42C	0.895 (18)	C8D—H8D	0.9500
N5C—C6C	1.339 (3)	C9D—C10D	1.382 (5)
C6C—C7C	1.495 (4)	C9D—H9D	0.9500
C7C—C12C	1.388 (4)	C10D—C11D	1.378 (5)
C7C—C8C	1.397 (4)	C10D—H10D	0.9500
C8C—C9C	1.387 (4)	C11D—C12D	1.390 (4)
C8C—H8C	0.9500	C11D—H11D	0.9500
C9C—C10C	1.388 (5)	C12D—H12D	0.9500
C9C—H9C	0.9500	C1X—O11X	1.233 (4)
C10C—C11C	1.371 (5)	C1X—N2X	1.323 (4)
C10C—H10C	0.9500	C1X—H1X	0.9500
C11C—C12C	1.399 (4)	N2X—C4X	1.455 (4)
C11C—H11C	0.9500	N2X—C3X	1.457 (4)
C12C—H12C	0.9500	C3X—H3X1	0.9800
N1B—C2B	1.358 (4)	C3X—H3X2	0.9800
N1B—C6B	1.374 (4)	C3X—H3X3	0.9800
N1B—H1B	0.862 (18)	C4X—H4X1	0.9800
C2B—N3B	1.353 (4)	C4X—H4X2	0.9800
C2B—S21B	1.669 (3)	C4X—H4X3	0.9800
N3B—C4B	1.388 (4)
C2A—N1A—C6A	123.4 (2)	O41B—C4B—N3B	120.5 (3)
C2A—N1A—H1A	114 (2)	O41B—C4B—C5B	124.1 (3)
C6A—N1A—H1A	122 (2)	N3B—C4B—C5B	115.4 (3)
N1A—C2A—N3A	114.9 (2)	C6B—C5B—C4B	118.2 (3)
N1A—C2A—S21A	122.59 (19)	C6B—C5B—C51B	123.0 (3)
N3A—C2A—S21A	122.5 (2)	C4B—C5B—C51B	118.7 (3)
C2A—N3A—C4A	125.9 (2)	C5B—C51B—H51B	109.5
C2A—N3A—H3A	118.2 (19)	C5B—C51B—H52B	109.5
C4A—N3A—H3A	115.5 (19)	H51B—C51B—H52B	109.5
O41A—C4A—N3A	120.0 (2)	C5B—C51B—H53B	109.5
O41A—C4A—C5A	124.3 (3)	H51B—C51B—H53B	109.5
N3A—C4A—C5A	115.6 (2)	H52B—C51B—H53B	109.5
C6A—C5A—C4A	117.7 (3)	C5B—C6B—N1B	122.1 (3)
C6A—C5A—C51A	123.8 (3)	C5B—C6B—H6B	119.0
C4A—C5A—C51A	118.4 (2)	N1B—C6B—H6B	119.0
C5A—C51A—H51A	109.5	C6D—N1D—C2D	115.5 (3)
C5A—C51A—H52A	109.5	N21D—C2D—N1D	116.5 (3)
H51A—C51A—H52A	109.5	N21D—C2D—N3D	118.3 (3)
C5A—C51A—H53A	109.5	N1D—C2D—N3D	125.1 (3)
H51A—C51A—H53A	109.5	C2D—N21D—H21D	121 (3)
H52A—C51A—H53A	109.5	C2D—N21D—H22D	118 (3)
C5A—C6A—N1A	122.3 (3)	H21D—N21D—H22D	118 (4)
C5A—C6A—H6A	118.9	C4D—N3D—C2D	113.7 (3)
N1A—C6A—H6A	118.9	N3D—C4D—N41D	116.5 (3)
C6C—N1C—C2C	114.9 (2)	N3D—C4D—N5D	126.4 (3)
N21C—C2C—N1C	117.0 (2)	N41D—C4D—N5D	117.1 (3)
N21C—C2C—N3C	117.8 (2)	C4D—N41D—H41D	118 (2)
N1C—C2C—N3C	125.2 (2)	C4D—N41D—H42D	123 (2)
C2C—N21C—H21C	115 (2)	H41D—N41D—H42D	118 (3)
C2C—N21C—H22C	120 (2)	C6D—N5D—C4D	113.6 (3)
H21C—N21C—H22C	116 (3)	N1D—C6D—N5D	125.6 (3)
C4C—N3C—C2C	113.9 (2)	N1D—C6D—C7D	115.4 (3)
N5C—C4C—N41C	116.8 (2)	N5D—C6D—C7D	118.9 (3)
N5C—C4C—N3C	125.8 (2)	C12D—C7D—C8D	118.2 (3)
N41C—C4C—N3C	117.3 (2)	C12D—C7D—C6D	122.1 (3)
C4C—N41C—H41C	117 (2)	C8D—C7D—C6D	119.6 (3)
C4C—N41C—H42C	118 (2)	C9D—C8D—C7D	121.3 (3)
H41C—N41C—H42C	123 (3)	C9D—C8D—H8D	119.4
C6C—N5C—C4C	114.1 (2)	C7D—C8D—H8D	119.4
N1C—C6C—N5C	126.0 (2)	C10D—C9D—C8D	119.9 (3)
N1C—C6C—C7C	116.0 (2)	C10D—C9D—H9D	120.1
N5C—C6C—C7C	118.0 (2)	C8D—C9D—H9D	120.1
C12C—C7C—C8C	120.2 (2)	C11D—C10D—C9D	119.5 (3)
C12C—C7C—C6C	120.2 (2)	C11D—C10D—H10D	120.3
C8C—C7C—C6C	119.5 (3)	C9D—C10D—H10D	120.3
C9C—C8C—C7C	119.6 (3)	C10D—C11D—C12D	120.4 (3)
C9C—C8C—H8C	120.2	C10D—C11D—H11D	119.8
C7C—C8C—H8C	120.2	C12D—C11D—H11D	119.8
C8C—C9C—C10C	119.9 (3)	C7D—C12D—C11D	120.6 (3)
C8C—C9C—H9C	120.1	C7D—C12D—H12D	119.7
C10C—C9C—H9C	120.1	C11D—C12D—H12D	119.7
C11C—C10C—C9C	120.9 (3)	O11X—C1X—N2X	124.8 (3)
C11C—C10C—H10C	119.6	O11X—C1X—H1X	117.6
C9C—C10C—H10C	119.6	N2X—C1X—H1X	117.6
C10C—C11C—C12C	119.8 (3)	C1X—N2X—C4X	121.5 (3)
C10C—C11C—H11C	120.1	C1X—N2X—C3X	120.5 (3)
C12C—C11C—H11C	120.1	C4X—N2X—C3X	117.9 (3)
C7C—C12C—C11C	119.6 (3)	N2X—C3X—H3X1	109.5
C7C—C12C—H12C	120.2	N2X—C3X—H3X2	109.5
C11C—C12C—H12C	120.2	H3X1—C3X—H3X2	109.5
C2B—N1B—C6B	122.6 (3)	N2X—C3X—H3X3	109.5
C2B—N1B—H1B	118 (2)	H3X1—C3X—H3X3	109.5
C6B—N1B—H1B	119 (2)	H3X2—C3X—H3X3	109.5
N3B—C2B—N1B	115.3 (3)	N2X—C4X—H4X1	109.5
N3B—C2B—S21B	123.4 (2)	N2X—C4X—H4X2	109.5
N1B—C2B—S21B	121.3 (2)	H4X1—C4X—H4X2	109.5
C2B—N3B—C4B	126.3 (3)	N2X—C4X—H4X3	109.5
C2B—N3B—H3B	116 (2)	H4X1—C4X—H4X3	109.5
C4B—N3B—H3B	118 (2)	H4X2—C4X—H4X3	109.5
C6A—N1A—C2A—N3A	0.5 (4)	C6B—N1B—C2B—S21B	175.4 (3)
C6A—N1A—C2A—S21A	−179.7 (2)	N1B—C2B—N3B—C4B	5.1 (5)
N1A—C2A—N3A—C4A	−4.1 (4)	S21B—C2B—N3B—C4B	−174.7 (3)
S21A—C2A—N3A—C4A	176.1 (2)	C2B—N3B—C4B—O41B	176.9 (3)
C2A—N3A—C4A—O41A	−173.7 (3)	C2B—N3B—C4B—C5B	−2.8 (5)
C2A—N3A—C4A—C5A	5.1 (4)	O41B—C4B—C5B—C6B	179.9 (3)
O41A—C4A—C5A—C6A	176.3 (3)	N3B—C4B—C5B—C6B	−0.4 (5)
N3A—C4A—C5A—C6A	−2.5 (4)	O41B—C4B—C5B—C51B	−3.3 (5)
O41A—C4A—C5A—C51A	−0.8 (5)	N3B—C4B—C5B—C51B	176.3 (3)
N3A—C4A—C5A—C51A	−179.6 (3)	C4B—C5B—C6B—N1B	1.0 (5)
C4A—C5A—C6A—N1A	−0.7 (4)	C51B—C5B—C6B—N1B	−175.6 (3)
C51A—C5A—C6A—N1A	176.2 (3)	C2B—N1B—C6B—C5B	1.6 (5)
C2A—N1A—C6A—C5A	1.8 (5)	C6D—N1D—C2D—N21D	−176.4 (4)
C6C—N1C—C2C—N21C	−177.6 (3)	C6D—N1D—C2D—N3D	2.3 (5)
C6C—N1C—C2C—N3C	2.4 (4)	N21D—C2D—N3D—C4D	177.6 (4)
N21C—C2C—N3C—C4C	178.0 (3)	N1D—C2D—N3D—C4D	−1.0 (5)
N1C—C2C—N3C—C4C	−2.0 (4)	C2D—N3D—C4D—N41D	−179.6 (3)
C2C—N3C—C4C—N5C	0.1 (4)	C2D—N3D—C4D—N5D	−1.8 (5)
C2C—N3C—C4C—N41C	−179.0 (3)	N3D—C4D—N5D—C6D	3.1 (5)
N41C—C4C—N5C—C6C	−179.8 (3)	N41D—C4D—N5D—C6D	−179.2 (3)
N3C—C4C—N5C—C6C	1.0 (4)	C2D—N1D—C6D—N5D	−0.9 (5)
C2C—N1C—C6C—N5C	−1.0 (4)	C2D—N1D—C6D—C7D	176.7 (3)
C2C—N1C—C6C—C7C	178.8 (3)	C4D—N5D—C6D—N1D	−1.6 (5)
C4C—N5C—C6C—N1C	−0.5 (4)	C4D—N5D—C6D—C7D	−179.1 (3)
C4C—N5C—C6C—C7C	179.7 (3)	N1D—C6D—C7D—C12D	−172.6 (3)
N1C—C6C—C7C—C12C	135.0 (3)	N5D—C6D—C7D—C12D	5.2 (4)
N5C—C6C—C7C—C12C	−45.2 (4)	N1D—C6D—C7D—C8D	4.0 (4)
N1C—C6C—C7C—C8C	−40.8 (4)	N5D—C6D—C7D—C8D	−178.2 (3)
N5C—C6C—C7C—C8C	139.0 (3)	C12D—C7D—C8D—C9D	1.2 (5)
C12C—C7C—C8C—C9C	1.4 (4)	C6D—C7D—C8D—C9D	−175.5 (3)
C6C—C7C—C8C—C9C	177.2 (3)	C7D—C8D—C9D—C10D	−0.2 (5)
C7C—C8C—C9C—C10C	−2.7 (5)	C8D—C9D—C10D—C11D	−2.1 (5)
C8C—C9C—C10C—C11C	1.6 (5)	C9D—C10D—C11D—C12D	3.2 (6)
C9C—C10C—C11C—C12C	0.9 (5)	C8D—C7D—C12D—C11D	−0.1 (5)
C8C—C7C—C12C—C11C	1.1 (4)	C6D—C7D—C12D—C11D	176.5 (3)
C6C—C7C—C12C—C11C	−174.7 (3)	C10D—C11D—C12D—C7D	−2.1 (6)
C10C—C11C—C12C—C7C	−2.2 (5)	O11X—C1X—N2X—C4X	179.1 (3)
C6B—N1B—C2B—N3B	−4.4 (5)	O11X—C1X—N2X—C3X	1.5 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N1C^i	0.85 (2)	2.13 (2)	2.946 (3)	162 (3)
N3A—H3A···N3C	0.89 (2)	2.21 (2)	3.099 (3)	174 (3)
N1B—H1B···O11X	0.86 (2)	1.92 (2)	2.771 (3)	169 (3)
N3B—H3B···N3D	0.88 (2)	2.23 (2)	3.107 (3)	177 (3)
N21C—H21C···S21A^ii	0.86 (2)	2.63 (2)	3.483 (2)	170 (3)
N21C—H22C···O41A	0.87 (2)	1.97 (2)	2.840 (3)	175 (3)
N41C—H41C···S21A	0.88 (2)	2.54 (2)	3.413 (2)	173 (3)
N41C—H42C···N5C^iii	0.90 (2)	2.15 (2)	3.042 (3)	173 (3)
N21D—H21D···O11X^iv	0.89 (2)	2.09 (2)	2.934 (4)	159 (4)
N21D—H22D···O41B	0.89 (2)	1.96 (2)	2.840 (4)	167 (4)
N41D—H41D···S21B	0.88 (2)	2.58 (2)	3.436 (3)	165 (3)
N41D—H42D···N5D^v	0.89 (2)	2.40 (2)	3.275 (4)	170 (3)
C10C—H10C···O41A^vi	0.95	2.54	3.350 (4)	143

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+2, −y, −z+1; (iv) x+1/2, −y+3/2, z+1/2; (v) −x+1, −y+1, −z+1; (vi) −x+5/2, y−1/2, −z+3/2.

5-Methyl-2-thiouracil–6-amino-3H-isocytosine–N,N-dimethylformamide (2/2/1) (IV)

Crystal data

2C5H6N2OS·2C4H6N4O·C3H7NO	F(000) = 1280
Mr = 609.71	Dx = 1.423 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 22.573 (3) Å	Cell parameters from 13239 reflections
b = 9.1593 (12) Å	θ = 3.2–26.2°
c = 13.9211 (16) Å	µ = 0.25 mm^−1
β = 98.701 (10)°	T = 173 K
V = 2845.1 (6) Å^3	Block, colourless
Z = 4	0.15 × 0.10 × 0.07 mm

Data collection

STOE IPDS II two-circle diffractometer	2052 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.122
ω scans	θmax = 25.9°, θmin = 3.2°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −27→27
Tmin = 0.362, Tmax = 1.000	k = −10→11
11737 measured reflections	l = −16→17
2741 independent reflections

Refinement

Refinement on F^2	15 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0529P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
2741 reflections	Δρmax = 0.47 e Å^−3
228 parameters	Δρmin = −0.21 e Å^−3

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1A	0.25804 (9)	0.5870 (2)	0.68791 (13)	0.0276 (4)
H1A	0.2737 (12)	0.590 (3)	0.7497 (13)	0.033*
C2A	0.28461 (10)	0.5045 (3)	0.62657 (15)	0.0250 (5)
S21A	0.34920 (3)	0.41635 (8)	0.66439 (4)	0.0320 (2)
N3A	0.25635 (9)	0.5023 (2)	0.53334 (13)	0.0265 (4)
H3A	0.2719 (12)	0.450 (3)	0.4914 (18)	0.032*
C4A	0.20409 (11)	0.5776 (3)	0.49760 (16)	0.0283 (5)
O41A	0.18212 (9)	0.5617 (2)	0.41215 (12)	0.0414 (5)
C5A	0.18093 (11)	0.6718 (3)	0.56548 (18)	0.0306 (6)
C51A	0.12694 (13)	0.7639 (3)	0.5318 (2)	0.0441 (7)
H51A	0.1187	0.8270	0.5851	0.066*
H51B	0.0923	0.7006	0.5115	0.066*
H51C	0.1345	0.8243	0.4769	0.066*
C6A	0.20850 (11)	0.6704 (3)	0.65809 (17)	0.0308 (6)
H6A	0.1929	0.7295	0.7045	0.037*
N1B	0.43554 (9)	0.0600 (2)	0.40837 (13)	0.0267 (5)
C2B	0.42522 (10)	0.1474 (3)	0.47932 (15)	0.0249 (5)
N21B	0.46111 (10)	0.1394 (3)	0.56472 (14)	0.0340 (5)
H21B	0.4922 (11)	0.080 (3)	0.570 (2)	0.041*
H22B	0.4568 (14)	0.202 (3)	0.6102 (18)	0.041*
N3B	0.38020 (9)	0.2451 (2)	0.46922 (13)	0.0282 (5)
H3B	0.3711 (12)	0.292 (3)	0.5202 (17)	0.034*
C4B	0.34121 (11)	0.2632 (3)	0.38263 (15)	0.0269 (5)
O41B	0.30123 (8)	0.3593 (2)	0.38019 (11)	0.0332 (4)
C5B	0.35140 (11)	0.1717 (3)	0.30740 (15)	0.0282 (5)
H5B	0.3267	0.1775	0.2459	0.034*
C6B	0.39779 (11)	0.0719 (3)	0.32273 (16)	0.0283 (5)
N61B	0.40827 (11)	−0.0195 (3)	0.25269 (15)	0.0380 (6)
H61B	0.3866 (12)	−0.010 (4)	0.1959 (15)	0.046*
H62B	0.4333 (13)	−0.090 (3)	0.263 (2)	0.046*
O11X	0.5000	0.2887 (3)	0.7500	0.0411 (7)
N2X	0.4953 (12)	0.5328 (5)	0.7625 (11)	0.050 (2)	0.5
C1X	0.5071 (3)	0.4131 (5)	0.7191 (4)	0.0373 (12)	0.5
H1X	0.5223	0.4217	0.6593	0.045*	0.5
C3X	0.4846 (3)	0.5240 (8)	0.8626 (5)	0.0565 (17)	0.5
H3XA	0.5118	0.5906	0.9029	0.085*	0.5
H3XB	0.4917	0.4238	0.8863	0.085*	0.5
H3XC	0.4430	0.5515	0.8660	0.085*	0.5
C4X	0.4965 (5)	0.6753 (7)	0.7160 (6)	0.074 (3)	0.5
H4XA	0.4566	0.7195	0.7092	0.112*	0.5
H4XB	0.5085	0.6635	0.6516	0.112*	0.5
H4XC	0.5254	0.7387	0.7560	0.112*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0283 (10)	0.0340 (12)	0.0188 (9)	−0.0052 (9)	−0.0018 (8)	−0.0044 (9)
C2A	0.0257 (12)	0.0288 (13)	0.0193 (10)	−0.0077 (10)	−0.0006 (9)	−0.0004 (10)
S21A	0.0282 (3)	0.0450 (4)	0.0201 (3)	0.0047 (3)	−0.0050 (2)	0.0019 (3)
N3A	0.0284 (11)	0.0321 (12)	0.0170 (9)	0.0003 (9)	−0.0025 (8)	−0.0029 (8)
C4A	0.0255 (12)	0.0322 (14)	0.0246 (11)	−0.0051 (10)	−0.0048 (9)	0.0024 (10)
O41A	0.0390 (11)	0.0571 (13)	0.0232 (8)	0.0018 (9)	−0.0109 (7)	0.0003 (9)
C5A	0.0254 (12)	0.0317 (14)	0.0334 (12)	−0.0037 (10)	0.0004 (10)	0.0026 (11)
C51A	0.0345 (15)	0.0459 (18)	0.0503 (16)	0.0053 (13)	0.0013 (12)	0.0098 (14)
C6A	0.0303 (13)	0.0326 (14)	0.0291 (12)	−0.0024 (10)	0.0033 (10)	−0.0066 (11)
N1B	0.0283 (11)	0.0307 (12)	0.0184 (9)	0.0027 (8)	−0.0057 (8)	−0.0021 (8)
C2B	0.0250 (11)	0.0297 (13)	0.0186 (10)	−0.0014 (10)	−0.0015 (8)	0.0025 (9)
N21B	0.0388 (12)	0.0416 (14)	0.0177 (9)	0.0112 (10)	−0.0079 (9)	−0.0054 (9)
N3B	0.0323 (11)	0.0350 (12)	0.0152 (8)	0.0050 (9)	−0.0029 (8)	−0.0020 (8)
C4B	0.0284 (12)	0.0314 (14)	0.0187 (10)	0.0001 (10)	−0.0034 (9)	0.0050 (10)
O41B	0.0359 (9)	0.0408 (11)	0.0202 (8)	0.0131 (8)	−0.0045 (7)	0.0006 (7)
C5B	0.0314 (13)	0.0341 (14)	0.0161 (10)	0.0040 (10)	−0.0062 (9)	−0.0002 (10)
C6B	0.0295 (13)	0.0331 (14)	0.0202 (10)	0.0018 (11)	−0.0036 (9)	−0.0013 (10)
N61B	0.0422 (13)	0.0468 (15)	0.0206 (10)	0.0169 (11)	−0.0097 (9)	−0.0100 (10)
O11X	0.0599 (18)	0.0333 (17)	0.0253 (12)	0.000	−0.0091 (12)	0.000
N2X	0.026 (7)	0.038 (3)	0.088 (7)	−0.003 (3)	0.016 (5)	−0.004 (4)
C1X	0.039 (3)	0.034 (3)	0.036 (3)	−0.001 (3)	−0.004 (2)	0.010 (2)
C3X	0.063 (4)	0.047 (4)	0.061 (4)	0.000 (3)	0.013 (3)	−0.019 (3)
C4X	0.090 (6)	0.031 (3)	0.102 (7)	−0.006 (4)	0.014 (8)	0.014 (3)

Geometric parameters (Å, º)

N1A—C2A	1.347 (3)	N3B—C4B	1.391 (3)
N1A—C6A	1.366 (3)	N3B—H3B	0.882 (17)
N1A—H1A	0.880 (18)	C4B—O41B	1.257 (3)
C2A—N3A	1.357 (3)	C4B—C5B	1.388 (3)
C2A—S21A	1.680 (3)	C5B—C6B	1.381 (4)
N3A—C4A	1.392 (3)	C5B—H5B	0.9500
N3A—H3A	0.872 (17)	C6B—N61B	1.334 (3)
C4A—O41A	1.226 (3)	N61B—H61B	0.869 (18)
C4A—C5A	1.435 (4)	N61B—H62B	0.855 (18)
C5A—C6A	1.344 (4)	O11X—C1X	1.237 (5)
C5A—C51A	1.498 (4)	N2X—C1X	1.299 (7)
C51A—H51A	0.9800	N2X—C3X	1.452 (9)
C51A—H51B	0.9800	N2X—C4X	1.459 (9)
C51A—H51C	0.9800	C1X—H1X	0.9500
C6A—H6A	0.9500	C3X—H3XA	0.9800
N1B—C2B	1.319 (3)	C3X—H3XB	0.9800
N1B—C6B	1.361 (3)	C3X—H3XC	0.9800
C2B—N21B	1.336 (3)	C4X—H4XA	0.9800
C2B—N3B	1.345 (3)	C4X—H4XB	0.9800
N21B—H21B	0.881 (18)	C4X—H4XC	0.9800
N21B—H22B	0.867 (18)
C2A—N1A—C6A	122.9 (2)	C2B—N3B—H3B	120.5 (19)
C2A—N1A—H1A	118.9 (19)	C4B—N3B—H3B	116.4 (19)
C6A—N1A—H1A	118.2 (19)	O41B—C4B—C5B	127.1 (2)
N1A—C2A—N3A	115.1 (2)	O41B—C4B—N3B	117.7 (2)
N1A—C2A—S21A	121.29 (17)	C5B—C4B—N3B	115.2 (2)
N3A—C2A—S21A	123.56 (18)	C6B—C5B—C4B	119.4 (2)
C2A—N3A—C4A	125.8 (2)	C6B—C5B—H5B	120.3
C2A—N3A—H3A	118 (2)	C4B—C5B—H5B	120.3
C4A—N3A—H3A	116 (2)	N61B—C6B—N1B	115.7 (2)
O41A—C4A—N3A	119.0 (2)	N61B—C6B—C5B	121.1 (2)
O41A—C4A—C5A	125.2 (2)	N1B—C6B—C5B	123.2 (2)
N3A—C4A—C5A	115.9 (2)	C6B—N61B—H61B	118 (2)
C6A—C5A—C4A	117.6 (2)	C6B—N61B—H62B	123 (2)
C6A—C5A—C51A	122.8 (3)	H61B—N61B—H62B	119 (3)
C4A—C5A—C51A	119.5 (2)	C1X—N2X—C3X	118.4 (7)
C5A—C51A—H51A	109.5	C1X—N2X—C4X	122.0 (8)
C5A—C51A—H51B	109.5	C3X—N2X—C4X	119.5 (6)
H51A—C51A—H51B	109.5	O11X—C1X—N2X	124.7 (5)
C5A—C51A—H51C	109.5	O11X—C1X—H1X	117.7
H51A—C51A—H51C	109.5	N2X—C1X—H1X	117.7
H51B—C51A—H51C	109.5	N2X—C3X—H3XA	109.5
C5A—C6A—N1A	122.4 (2)	N2X—C3X—H3XB	109.5
C5A—C6A—H6A	118.8	H3XA—C3X—H3XB	109.5
N1A—C6A—H6A	118.8	N2X—C3X—H3XC	109.5
C2B—N1B—C6B	116.7 (2)	H3XA—C3X—H3XC	109.5
N1B—C2B—N21B	118.8 (2)	H3XB—C3X—H3XC	109.5
N1B—C2B—N3B	122.8 (2)	N2X—C4X—H4XA	109.5
N21B—C2B—N3B	118.5 (2)	N2X—C4X—H4XB	109.5
C2B—N21B—H21B	119 (2)	H4XA—C4X—H4XB	109.5
C2B—N21B—H22B	120 (2)	N2X—C4X—H4XC	109.5
H21B—N21B—H22B	121 (3)	H4XA—C4X—H4XC	109.5
C2B—N3B—C4B	122.6 (2)	H4XB—C4X—H4XC	109.5
C6A—N1A—C2A—N3A	−4.1 (3)	C6B—N1B—C2B—N3B	−0.4 (3)
C6A—N1A—C2A—S21A	174.07 (19)	N1B—C2B—N3B—C4B	−0.8 (4)
N1A—C2A—N3A—C4A	0.7 (4)	N21B—C2B—N3B—C4B	178.8 (2)
S21A—C2A—N3A—C4A	−177.5 (2)	C2B—N3B—C4B—O41B	−178.8 (2)
C2A—N3A—C4A—O41A	−177.4 (2)	C2B—N3B—C4B—C5B	0.9 (3)
C2A—N3A—C4A—C5A	3.9 (4)	O41B—C4B—C5B—C6B	179.8 (3)
O41A—C4A—C5A—C6A	176.3 (3)	N3B—C4B—C5B—C6B	0.1 (3)
N3A—C4A—C5A—C6A	−5.1 (3)	C2B—N1B—C6B—N61B	−178.6 (2)
O41A—C4A—C5A—C51A	−2.2 (4)	C2B—N1B—C6B—C5B	1.5 (4)
N3A—C4A—C5A—C51A	176.4 (2)	C4B—C5B—C6B—N61B	178.8 (3)
C4A—C5A—C6A—N1A	2.1 (4)	C4B—C5B—C6B—N1B	−1.4 (4)
C51A—C5A—C6A—N1A	−179.4 (2)	C3X—N2X—C1X—O11X	13 (3)
C2A—N1A—C6A—C5A	2.8 (4)	C4X—N2X—C1X—O11X	−171.1 (13)
C6B—N1B—C2B—N21B	179.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O41B^i	0.88 (2)	1.89 (2)	2.751 (2)	167 (3)
N3A—H3A···O41B	0.87 (2)	1.96 (2)	2.818 (3)	169 (3)
N21B—H21B···N1B^ii	0.88 (2)	2.06 (2)	2.942 (3)	177 (3)
N21B—H22B···O11X	0.87 (2)	2.19 (2)	2.934 (2)	143 (3)
N3B—H3B···S21A	0.88 (2)	2.42 (2)	3.303 (2)	178 (3)
C5B—H5B···O41A^iii	0.95	2.42	3.198 (3)	139
N61B—H61B···O41A^iii	0.87 (2)	2.10 (2)	2.927 (3)	160 (3)
N61B—H62B···O11X^ii	0.86 (2)	2.39 (2)	3.223 (3)	166 (3)

Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x+1, −y, −z+1; (iii) −x+1/2, y−1/2, −z+1/2.

5-Methyl-2-thiouracil–6-amino-3H-isocytosine–N,N-dimethylacetamide (2/2/1) (V)

Crystal data

2C5H6N2OS·2C4H6N4O·C4H9NO	F(000) = 1312
Mr = 623.73	Dx = 1.449 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 23.530 (3) Å	Cell parameters from 9945 reflections
b = 8.7478 (9) Å	θ = 3.5–26.1°
c = 14.2006 (16) Å	µ = 0.25 mm^−1
β = 102.037 (10)°	T = 173 K
V = 2858.7 (6) Å^3	Block, colourless
Z = 4	0.23 × 0.21 × 0.16 mm

Data collection

STOE IPDS II two-circle diffractometer	1896 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.052
ω scans	θmax = 26.0°, θmin = 3.5°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −28→27
Tmin = 0.684, Tmax = 1.000	k = −10→10
11932 measured reflections	l = −16→17
2766 independent reflections

Refinement

Refinement on F^2	18 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.0381P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.001
2766 reflections	Δρmax = 0.17 e Å^−3
234 parameters	Δρmin = −0.22 e Å^−3

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1A	0.25885 (9)	0.5771 (2)	0.68612 (14)	0.0317 (5)
H1A	0.2759 (10)	0.581 (3)	0.7484 (13)	0.038*
C2A	0.28519 (10)	0.4980 (3)	0.62690 (16)	0.0277 (5)
S21A	0.34844 (3)	0.40642 (8)	0.66780 (5)	0.03738 (19)
N3A	0.25790 (9)	0.4997 (2)	0.53269 (14)	0.0300 (5)
H3A	0.2743 (10)	0.451 (3)	0.4920 (16)	0.036*
C4A	0.20664 (10)	0.5790 (3)	0.49381 (17)	0.0322 (6)
O41A	0.18585 (8)	0.5684 (2)	0.40747 (12)	0.0459 (5)
C5A	0.18328 (10)	0.6696 (3)	0.56098 (18)	0.0333 (6)
C51A	0.12997 (12)	0.7649 (3)	0.5241 (2)	0.0475 (7)
H51A	0.0964	0.6976	0.5035	0.071*
H51B	0.1359	0.8266	0.4694	0.071*
H51C	0.1229	0.8324	0.5756	0.071*
C6A	0.21014 (11)	0.6632 (3)	0.65403 (19)	0.0355 (6)
H6A	0.1947	0.7209	0.6995	0.043*
N1B	0.43409 (8)	0.0547 (2)	0.41269 (14)	0.0295 (5)
C2B	0.42413 (10)	0.1408 (3)	0.48397 (17)	0.0292 (5)
N21B	0.45901 (10)	0.1257 (3)	0.57079 (15)	0.0400 (6)
H21B	0.4895 (9)	0.064 (3)	0.572 (2)	0.048*
H22B	0.4576 (12)	0.194 (3)	0.6143 (17)	0.048*
N3B	0.37991 (9)	0.2428 (2)	0.47321 (14)	0.0324 (5)
H3B	0.3733 (11)	0.294 (3)	0.5257 (14)	0.039*
C4B	0.34171 (10)	0.2663 (3)	0.38474 (16)	0.0302 (6)
O41B	0.30261 (8)	0.3656 (2)	0.38063 (12)	0.0385 (5)
C5B	0.35193 (10)	0.1756 (3)	0.31003 (16)	0.0309 (6)
H5B	0.3281	0.1860	0.2476	0.037*
C6B	0.39636 (11)	0.0709 (3)	0.32578 (17)	0.0322 (6)
N61B	0.40561 (10)	−0.0223 (3)	0.25604 (15)	0.0401 (6)
H61B	0.3840 (12)	−0.015 (3)	0.1984 (15)	0.048*
H62B	0.4301 (11)	−0.100 (3)	0.267 (2)	0.048*
O21X	0.5000	0.2981 (3)	0.7500	0.0380 (6)
C32X	0.5000	0.7079 (5)	0.7500	0.107 (2)
H4XA	0.5034	0.7774	0.8050	0.160*	0.5
H4XB	0.4640	0.7299	0.7033	0.160*	0.5
H4XC	0.5333	0.7222	0.7194	0.160*	0.5
C1X	0.5132 (11)	0.4808 (18)	0.6257 (9)	0.057 (5)	0.5
H1XA	0.4750	0.5012	0.5846	0.085*	0.5
H1XB	0.5322	0.3974	0.5980	0.085*	0.5
H1XC	0.5372	0.5731	0.6302	0.085*	0.5
C2X	0.5056 (3)	0.4358 (5)	0.7253 (3)	0.0324 (14)	0.5
N3X	0.4989 (2)	0.5475 (5)	0.7837 (3)	0.0361 (11)	0.5
C31X	0.4789 (9)	0.5120 (18)	0.8719 (8)	0.047 (3)	0.5
H3XA	0.4365	0.5203	0.8598	0.071*	0.5
H3XB	0.4962	0.5842	0.9225	0.071*	0.5
H3XC	0.4906	0.4077	0.8925	0.071*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0310 (11)	0.0408 (12)	0.0228 (10)	−0.0043 (9)	0.0042 (8)	−0.0043 (9)
C2A	0.0302 (13)	0.0296 (12)	0.0227 (12)	−0.0061 (10)	0.0041 (10)	0.0004 (10)
S21A	0.0345 (3)	0.0492 (4)	0.0260 (3)	0.0068 (3)	0.0007 (3)	0.0040 (3)
N3A	0.0302 (11)	0.0369 (12)	0.0224 (11)	0.0011 (9)	0.0041 (9)	−0.0027 (9)
C4A	0.0275 (12)	0.0351 (13)	0.0319 (14)	−0.0064 (11)	0.0012 (10)	0.0055 (11)
O41A	0.0419 (11)	0.0617 (12)	0.0285 (10)	0.0030 (9)	−0.0056 (8)	0.0015 (9)
C5A	0.0278 (13)	0.0327 (13)	0.0399 (15)	−0.0044 (10)	0.0080 (11)	0.0038 (11)
C51A	0.0370 (15)	0.0464 (16)	0.0598 (19)	0.0057 (12)	0.0115 (14)	0.0094 (14)
C6A	0.0336 (14)	0.0367 (14)	0.0382 (15)	−0.0041 (11)	0.0118 (12)	−0.0069 (11)
N1B	0.0317 (11)	0.0320 (11)	0.0226 (10)	−0.0003 (8)	0.0008 (8)	−0.0015 (8)
C2B	0.0332 (13)	0.0301 (13)	0.0230 (12)	−0.0026 (10)	0.0031 (10)	0.0022 (10)
N21B	0.0448 (13)	0.0503 (14)	0.0216 (11)	0.0123 (11)	−0.0007 (10)	−0.0055 (9)
N3B	0.0379 (12)	0.0368 (12)	0.0221 (10)	0.0032 (9)	0.0055 (9)	−0.0033 (9)
C4B	0.0338 (13)	0.0345 (13)	0.0213 (12)	−0.0027 (11)	0.0036 (10)	0.0031 (10)
O41B	0.0403 (10)	0.0467 (11)	0.0277 (9)	0.0137 (8)	0.0052 (8)	0.0034 (7)
C5B	0.0351 (13)	0.0355 (13)	0.0190 (12)	0.0012 (11)	−0.0016 (10)	−0.0023 (10)
C6B	0.0368 (13)	0.0336 (13)	0.0245 (13)	−0.0041 (11)	0.0028 (11)	−0.0011 (11)
N61B	0.0451 (14)	0.0450 (13)	0.0253 (11)	0.0135 (10)	−0.0039 (10)	−0.0091 (10)
O21X	0.0493 (16)	0.0340 (14)	0.0287 (13)	0.000	0.0037 (12)	0.000
C32X	0.176 (7)	0.034 (3)	0.147 (6)	0.000	0.118 (5)	0.000
C1X	0.072 (7)	0.062 (8)	0.044 (6)	−0.035 (6)	0.029 (5)	−0.004 (5)
C2X	0.027 (3)	0.042 (3)	0.027 (4)	0.002 (3)	0.005 (3)	0.004 (2)
N3X	0.043 (3)	0.034 (2)	0.035 (3)	−0.001 (2)	0.015 (3)	−0.0012 (17)
C31X	0.068 (8)	0.045 (5)	0.035 (5)	0.019 (6)	0.024 (4)	0.008 (3)

Geometric parameters (Å, º)

N1A—C2A	1.337 (3)	N3B—H3B	0.911 (17)
N1A—C6A	1.368 (3)	C4B—O41B	1.258 (3)
N1A—H1A	0.892 (16)	C4B—C5B	1.385 (3)
C2A—N3A	1.358 (3)	C5B—C6B	1.373 (3)
C2A—S21A	1.683 (2)	C5B—H5B	0.9500
N3A—C4A	1.401 (3)	C6B—N61B	1.335 (3)
N3A—H3A	0.870 (17)	N61B—H61B	0.871 (17)
C4A—O41A	1.225 (3)	N61B—H62B	0.882 (17)
C4A—C5A	1.435 (4)	O21X—C2X	1.269 (5)
C5A—C6A	1.342 (3)	C32X—N3X	1.484 (5)
C5A—C51A	1.506 (3)	C32X—H4XA	0.9800
C51A—H51A	0.9800	C32X—H4XB	0.9800
C51A—H51B	0.9800	C32X—H4XC	0.9800
C51A—H51C	0.9800	C1X—C2X	1.513 (8)
C6A—H6A	0.9500	C1X—H1XA	0.9800
N1B—C2B	1.321 (3)	C1X—H1XB	0.9800
N1B—C6B	1.369 (3)	C1X—H1XC	0.9800
C2B—N21B	1.338 (3)	C2X—N3X	1.313 (5)
C2B—N3B	1.355 (3)	N3X—C31X	1.460 (8)
N21B—H21B	0.894 (17)	C31X—H3XA	0.9800
N21B—H22B	0.866 (17)	C31X—H3XB	0.9800
N3B—C4B	1.399 (3)	C31X—H3XC	0.9800
C2A—N1A—C6A	122.8 (2)	O41B—C4B—N3B	118.0 (2)
C2A—N1A—H1A	118.1 (17)	C5B—C4B—N3B	115.0 (2)
C6A—N1A—H1A	118.8 (17)	C6B—C5B—C4B	120.3 (2)
N1A—C2A—N3A	115.3 (2)	C6B—C5B—H5B	119.8
N1A—C2A—S21A	121.45 (17)	C4B—C5B—H5B	119.8
N3A—C2A—S21A	123.2 (2)	N61B—C6B—N1B	115.5 (2)
C2A—N3A—C4A	125.8 (2)	N61B—C6B—C5B	121.5 (2)
C2A—N3A—H3A	117.8 (17)	N1B—C6B—C5B	123.0 (2)
C4A—N3A—H3A	116.4 (17)	C6B—N61B—H61B	120 (2)
O41A—C4A—N3A	119.2 (2)	C6B—N61B—H62B	122.2 (18)
O41A—C4A—C5A	125.4 (2)	H61B—N61B—H62B	118 (3)
N3A—C4A—C5A	115.4 (2)	N3X—C32X—H4XA	109.5
C6A—C5A—C4A	117.7 (2)	N3X—C32X—H4XB	109.5
C6A—C5A—C51A	123.5 (3)	H4XA—C32X—H4XB	109.5
C4A—C5A—C51A	118.8 (2)	N3X—C32X—H4XC	109.5
C5A—C51A—H51A	109.5	H4XA—C32X—H4XC	109.5
C5A—C51A—H51B	109.5	H4XB—C32X—H4XC	109.5
H51A—C51A—H51B	109.5	C2X—C1X—H1XA	109.5
C5A—C51A—H51C	109.5	C2X—C1X—H1XB	109.5
H51A—C51A—H51C	109.5	H1XA—C1X—H1XB	109.5
H51B—C51A—H51C	109.5	C2X—C1X—H1XC	109.5
C5A—C6A—N1A	122.7 (3)	H1XA—C1X—H1XC	109.5
C5A—C6A—H6A	118.6	H1XB—C1X—H1XC	109.5
N1A—C6A—H6A	118.6	O21X—C2X—N3X	119.8 (4)
C2B—N1B—C6B	116.5 (2)	O21X—C2X—C1X	123.0 (7)
N1B—C2B—N21B	118.5 (2)	N3X—C2X—C1X	116.8 (7)
N1B—C2B—N3B	122.9 (2)	C2X—N3X—C31X	119.1 (7)
N21B—C2B—N3B	118.6 (2)	C2X—N3X—C32X	119.1 (3)
C2B—N21B—H21B	114.5 (18)	C31X—N3X—C32X	120.6 (7)
C2B—N21B—H22B	118.8 (18)	N3X—C31X—H3XA	109.5
H21B—N21B—H22B	123 (3)	N3X—C31X—H3XB	109.5
C2B—N3B—C4B	122.2 (2)	H3XA—C31X—H3XB	109.5
C2B—N3B—H3B	119.4 (16)	N3X—C31X—H3XC	109.5
C4B—N3B—H3B	118.4 (16)	H3XA—C31X—H3XC	109.5
O41B—C4B—C5B	127.0 (2)	H3XB—C31X—H3XC	109.5
C6A—N1A—C2A—N3A	−4.5 (3)	N1B—C2B—N3B—C4B	−1.0 (4)
C6A—N1A—C2A—S21A	174.29 (19)	N21B—C2B—N3B—C4B	179.6 (2)
N1A—C2A—N3A—C4A	1.7 (3)	C2B—N3B—C4B—O41B	−178.5 (2)
S21A—C2A—N3A—C4A	−177.09 (19)	C2B—N3B—C4B—C5B	1.2 (3)
C2A—N3A—C4A—O41A	−178.5 (2)	O41B—C4B—C5B—C6B	−179.6 (3)
C2A—N3A—C4A—C5A	2.4 (3)	N3B—C4B—C5B—C6B	0.8 (3)
O41A—C4A—C5A—C6A	177.2 (2)	C2B—N1B—C6B—N61B	−177.0 (2)
N3A—C4A—C5A—C6A	−3.8 (3)	C2B—N1B—C6B—C5B	3.3 (4)
O41A—C4A—C5A—C51A	−2.1 (4)	C4B—C5B—C6B—N61B	177.1 (3)
N3A—C4A—C5A—C51A	176.9 (2)	C4B—C5B—C6B—N1B	−3.1 (4)
C4A—C5A—C6A—N1A	1.3 (4)	O21X—C2X—N3X—C31X	−6.5 (12)
C51A—C5A—C6A—N1A	−179.4 (2)	C1X—C2X—N3X—C31X	167 (2)
C2A—N1A—C6A—C5A	3.2 (4)	O21X—C2X—N3X—C32X	−174.1 (4)
C6B—N1B—C2B—N21B	178.2 (2)	C1X—C2X—N3X—C32X	−0.9 (13)
C6B—N1B—C2B—N3B	−1.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O41B^i	0.89 (2)	1.91 (2)	2.785 (2)	166 (2)
N3A—H3A···O41B	0.87 (2)	1.99 (2)	2.845 (3)	169 (2)
N21B—H21B···N1B^ii	0.89 (2)	2.05 (2)	2.937 (3)	172 (2)
N21B—H22B···O21X	0.87 (2)	2.18 (2)	2.942 (2)	147 (2)
N3B—H3B···S21A	0.91 (2)	2.42 (2)	3.329 (2)	173 (2)
C5B—H5B···O41A^iii	0.95	2.39	3.173 (3)	140
N61B—H61B···O41A^iii	0.87 (2)	2.11 (2)	2.927 (3)	156 (3)
N61B—H62B···O21X^ii	0.88 (2)	2.44 (2)	3.293 (3)	163 (3)

Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x+1, −y, −z+1; (iii) −x+1/2, y−1/2, −z+1/2.

5-Methyl-2-thiouracil–melamine (3/2) (VI)

Crystal data

3C5H6N2OS·2C3H6N6	Dx = 1.514 Mg m^−3
Mr = 678.81	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 19335 reflections
a = 17.6827 (7) Å	θ = 1.8–26.9°
c = 16.4925 (9) Å	µ = 0.31 mm^−1
V = 4466.0 (4) Å^3	T = 173 K
Z = 6	Block, colourless
F(000) = 2124	0.48 × 0.34 × 0.29 mm

Data collection

STOE IPDS II two-circle diffractometer	1960 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.056
ω scans	θmax = 26.3°, θmin = 1.8°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −22→22
Tmin = 0.828, Tmax = 1.000	k = −21→22
12864 measured reflections	l = −20→20
2026 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.036	w = 1/[σ^2(Fo^2) + (0.0518P)^2 + 3.6735P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.094	(Δ/σ)max = 0.001
S = 1.12	Δρmax = 0.25 e Å^−3
2026 reflections	Δρmin = −0.22 e Å^−3
166 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
6 restraints	Extinction coefficient: 0.0069 (8)

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1A	0.37482 (8)	0.44714 (8)	0.05842 (8)	0.0298 (3)
H1A	0.3727 (12)	0.4957 (10)	0.0599 (11)	0.036*
C2A	0.44133 (9)	0.44463 (9)	0.09504 (8)	0.0281 (3)
S21A	0.52440 (2)	0.53347 (2)	0.13923 (2)	0.03323 (17)
N3A	0.43706 (8)	0.36587 (8)	0.09583 (7)	0.0301 (3)
H3A	0.4820 (11)	0.3643 (12)	0.1173 (11)	0.036*
O41A	0.36336 (8)	0.21806 (7)	0.08003 (8)	0.0354 (4)	0.886 (4)
C4A	0.36721 (9)	0.28828 (9)	0.06634 (9)	0.0307 (3)
H4A	0.3634	0.2334	0.0751	0.037*	0.114 (4)
C5A	0.30145 (9)	0.29595 (9)	0.02209 (9)	0.0317 (3)
C51A	0.22838 (11)	0.21703 (10)	−0.01759 (11)	0.0399 (4)
H51A	0.1920	0.1750	0.0241	0.060*	0.886 (4)
H52A	0.2525	0.1900	−0.0533	0.060*	0.886 (4)
H53A	0.1928	0.2344	−0.0496	0.060*	0.886 (4)
H54A	0.2366	0.1667	−0.0092	0.060*	0.114 (4)
H55A	0.1726	0.2049	0.0063	0.060*	0.114 (4)
H56A	0.2281	0.2278	−0.0758	0.060*	0.114 (4)
C6A	0.30761 (9)	0.37550 (9)	0.02055 (9)	0.0301 (3)
H6A	0.2643	0.3821	−0.0075	0.036*	0.886 (4)
O61A	0.2517 (6)	0.3828 (6)	−0.0055 (6)	0.036 (3)	0.114 (4)
N1B	0.59548 (7)	0.34630 (7)	0.14233 (7)	0.0293 (3)
C2B	0.67898 (9)	0.41258 (8)	0.14251 (8)	0.0286 (3)
N21B	0.69157 (8)	0.49371 (8)	0.14360 (9)	0.0383 (3)
H21B	0.7446 (11)	0.5374 (11)	0.1373 (12)	0.046*
H22B	0.6434 (11)	0.5000 (13)	0.1451 (12)	0.046*
N1C	0.34975 (7)	0.59797 (7)	0.06677 (7)	0.0269 (3)
C2C	0.41382 (8)	0.68227 (8)	0.06760 (8)	0.0261 (3)
N21C	0.49633 (8)	0.69786 (8)	0.06915 (8)	0.0321 (3)
H21C	0.5370 (11)	0.7495 (10)	0.0849 (11)	0.039*
H22C	0.5035 (12)	0.6525 (11)	0.0820 (11)	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0264 (6)	0.0247 (6)	0.0420 (7)	0.0156 (5)	0.0000 (5)	−0.0018 (5)
C2A	0.0262 (6)	0.0262 (6)	0.0348 (7)	0.0153 (5)	0.0040 (5)	−0.0004 (5)
S21A	0.0257 (2)	0.0261 (2)	0.0506 (3)	0.01499 (15)	−0.00431 (13)	−0.00618 (13)
N3A	0.0292 (6)	0.0262 (6)	0.0394 (6)	0.0171 (5)	−0.0013 (5)	−0.0022 (5)
O41A	0.0319 (6)	0.0246 (6)	0.0527 (7)	0.0164 (5)	−0.0033 (5)	−0.0018 (5)
C4A	0.0312 (7)	0.0271 (7)	0.0367 (7)	0.0168 (6)	0.0018 (5)	−0.0023 (5)
C5A	0.0285 (7)	0.0292 (7)	0.0362 (7)	0.0135 (6)	0.0024 (5)	−0.0024 (5)
C51A	0.0357 (8)	0.0319 (8)	0.0498 (9)	0.0151 (6)	−0.0052 (6)	−0.0073 (6)
C6A	0.0255 (6)	0.0303 (7)	0.0363 (7)	0.0153 (6)	−0.0004 (5)	−0.0012 (5)
O61A	0.030 (5)	0.033 (5)	0.054 (6)	0.023 (4)	−0.014 (4)	−0.004 (4)
N1B	0.0232 (5)	0.0227 (6)	0.0420 (7)	0.0114 (4)	0.0009 (4)	0.0006 (4)
C2B	0.0251 (6)	0.0246 (6)	0.0367 (7)	0.0128 (5)	0.0011 (5)	−0.0007 (5)
N21B	0.0237 (6)	0.0223 (6)	0.0689 (9)	0.0114 (5)	0.0023 (6)	−0.0007 (5)
N1C	0.0223 (5)	0.0221 (5)	0.0367 (6)	0.0114 (4)	−0.0006 (4)	−0.0014 (4)
C2C	0.0238 (6)	0.0236 (6)	0.0306 (6)	0.0116 (5)	0.0013 (5)	−0.0004 (5)
N21C	0.0214 (6)	0.0247 (6)	0.0496 (7)	0.0111 (5)	0.0010 (5)	−0.0006 (5)

Geometric parameters (Å, º)

N1A—C2A	1.3425 (18)	C51A—H55A	0.9800
N1A—C6A	1.3790 (18)	C51A—H56A	0.9800
N1A—H1A	0.878 (14)	C6A—O61A	1.144 (8)
C2A—N3A	1.3566 (17)	C6A—H6A	0.9500
C2A—S21A	1.6879 (14)	N1B—C2B^i	1.3473 (17)
N3A—C4A	1.3964 (18)	N1B—C2B	1.3503 (17)
N3A—H3A	0.884 (14)	C2B—N21B	1.3373 (17)
O41A—C4A	1.2299 (18)	C2B—N1B^ii	1.3473 (17)
C4A—C5A	1.436 (2)	N21B—H21B	0.873 (15)
C4A—H4A	0.9500	N21B—H22B	0.913 (15)
C5A—C6A	1.356 (2)	N1C—C2C^iii	1.3455 (17)
C5A—C51A	1.497 (2)	N1C—C2C	1.3480 (17)
C51A—H51A	0.9800	C2C—N21C	1.3427 (17)
C51A—H52A	0.9800	C2C—N1C^iv	1.3455 (17)
C51A—H53A	0.9800	N21C—H21C	0.873 (15)
C51A—H54A	0.9800	N21C—H22C	0.898 (15)
C2A—N1A—C6A	122.70 (12)	C5A—C51A—H55A	109.5
C2A—N1A—H1A	119.0 (12)	H54A—C51A—H55A	109.5
C6A—N1A—H1A	118.2 (12)	C5A—C51A—H56A	109.5
N1A—C2A—N3A	115.99 (12)	H54A—C51A—H56A	109.5
N1A—C2A—S21A	122.18 (10)	H55A—C51A—H56A	109.5
N3A—C2A—S21A	121.81 (11)	O61A—C6A—C5A	120.0 (5)
C2A—N3A—C4A	124.98 (12)	O61A—C6A—N1A	117.6 (5)
C2A—N3A—H3A	116.6 (12)	C5A—C6A—N1A	122.00 (13)
C4A—N3A—H3A	118.5 (12)	C5A—C6A—H6A	119.0
O41A—C4A—N3A	120.23 (13)	N1A—C6A—H6A	119.0
O41A—C4A—C5A	123.37 (13)	C2B^i—N1B—C2B	113.99 (12)
N3A—C4A—C5A	116.39 (12)	N21B—C2B—N1B^ii	116.96 (12)
N3A—C4A—H4A	121.8	N21B—C2B—N1B	117.02 (12)
C5A—C4A—H4A	121.8	N1B^ii—C2B—N1B	126.01 (12)
C6A—C5A—C4A	117.32 (13)	C2B—N21B—H21B	118.4 (13)
C6A—C5A—C51A	122.88 (13)	C2B—N21B—H22B	117.8 (13)
C4A—C5A—C51A	119.77 (13)	H21B—N21B—H22B	123.4 (18)
C5A—C51A—H51A	109.5	C2C^iii—N1C—C2C	114.42 (12)
C5A—C51A—H52A	109.5	N21C—C2C—N1C^iv	117.48 (12)
H51A—C51A—H52A	109.5	N21C—C2C—N1C	116.96 (12)
C5A—C51A—H53A	109.5	N1C^iv—C2C—N1C	125.56 (12)
H51A—C51A—H53A	109.5	C2C—N21C—H21C	117.6 (12)
H52A—C51A—H53A	109.5	C2C—N21C—H22C	116.5 (12)
C5A—C51A—H54A	109.5	H21C—N21C—H22C	116.9 (17)
C6A—N1A—C2A—N3A	−2.7 (2)	C4A—C5A—C6A—O61A	−170.8 (6)
C6A—N1A—C2A—S21A	178.52 (11)	C51A—C5A—C6A—O61A	7.2 (7)
N1A—C2A—N3A—C4A	−4.1 (2)	C4A—C5A—C6A—N1A	1.2 (2)
S21A—C2A—N3A—C4A	174.65 (11)	C51A—C5A—C6A—N1A	179.11 (14)
C2A—N3A—C4A—O41A	−169.51 (14)	C2A—N1A—C6A—O61A	176.2 (6)
C2A—N3A—C4A—C5A	9.1 (2)	C2A—N1A—C6A—C5A	4.1 (2)
O41A—C4A—C5A—C6A	171.39 (14)	C2B^i—N1B—C2B—N21B	−179.01 (9)
N3A—C4A—C5A—C6A	−7.16 (19)	C2B^i—N1B—C2B—N1B^ii	0.4 (3)
O41A—C4A—C5A—C51A	−6.6 (2)	C2C^iii—N1C—C2C—N21C	178.17 (8)
N3A—C4A—C5A—C51A	174.82 (13)	C2C^iii—N1C—C2C—N1C^iv	−2.0 (3)

Symmetry codes: (i) −y+1, x−y, z; (ii) −x+y+1, −x+1, z; (iii) −x+y, −x+1, z; (iv) −y+1, x−y+1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N1C	0.88 (1)	2.05 (2)	2.9173 (16)	172 (2)
N3A—H3A···N1B	0.88 (1)	2.22 (2)	3.0861 (16)	166 (2)
C4A—H4A···O61A^v	0.95	2.31	3.093 (8)	140
C6A—H6A···O41A^vi	0.95	2.30	3.2278 (18)	167
N21B—H21B···O41A^ii	0.87 (2)	2.09 (2)	2.9184 (17)	159 (2)
N21B—H22B···S21A	0.91 (2)	2.46 (2)	3.3640 (13)	173 (2)
N21C—H21C···S21A^vii	0.87 (2)	2.72 (2)	3.5085 (13)	152 (2)
N21C—H21C···O61A^iv	0.87 (2)	2.39 (2)	2.960 (9)	124 (2)
N21C—H22C···S21A	0.90 (2)	2.50 (2)	3.3875 (13)	172 (2)

Symmetry codes: (ii) −x+y+1, −x+1, z; (iv) −y+1, x−y+1, z; (v) y, −x+y, −z; (vi) x−y, x, −z; (vii) x−y+2/3, x+1/3, −z+1/3.