Hydrogen bonding patterns in salts of derivatives of aminopyrimidine and thiobarbituric acid

Three salts, namely 2-amino-4,6-dimethylpyrimidin-1-ium thiobarbiturate trihydrate (I), 2-amino-4,6-dimethoxypyrimidin-1-ium thiobarbiturate dihydrate (II) and 2,4-di­amino-5-(3′,4′,5′-trimethoxybenzyl)pyrimidin-1-ium thiobarbiturate (III), were synthesized and characterized by IR and X-ray diffraction techniques. The primary interaction between the acid and base happens via N—H...O hydrogen bonds in (II) and (III), and via water-mediated N—H...OW and OW—HW...S in (I). The water molecules present in compound (I) form a (H₂O)₁₂ water cluster via water–water interactions. In all three compounds (I)–(III), thiobarbiturate anions form self-complementary pairs with a robust R₂²(8) motif via a pair of N—H...O/N—H...S hydrogen bonds. They mimic the nucleobase base pairs by utilizing the same groups (thymine/uracil uses N3—H and C4=O8 groups during the formation of Watson–Crick and Hoogsteen base pairs with adenine). Compound (I) forms a water-mediated base pair through N—H...OW hydrogen bonds and forms an R₄²(12) motif. The formation of N—H...S hydrogen bonds, water-mediated base pairs and water–water interactions in these crystal systems offers scope for these systems to be considered as a model in the study of hydration of nucleobases and water-mediated nucleobase base pairs in macromolecules.

Computing details

For all compounds, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009), Mercury (Macrae et al., 2008) and POVRay (Cason, 2004); software used to prepare material for publication: PLATON (Spek, 2009).

Figures

(AMPYTBA) 2-amino-4,6-dimethyl pyrimidin-1-ium thiobarbiturate trihydrate

Crystal data

C4H3N2O2S·C6H10N3·3(H2O)	Z = 4
Mr = 321.36	F(000) = 680
Triclinic, P1	Dx = 1.374 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.0229 (2) Å	Cell parameters from 9216 reflections
b = 12.1092 (3) Å	θ = 1.8–30.3°
c = 13.2095 (2) Å	µ = 0.24 mm^−1
α = 98.921 (1)°	T = 296 K
β = 115.403 (1)°	Prism, colorless
γ = 108.241 (1)°	0.13 × 0.11 × 0.08 mm
V = 1553.23 (5) Å^3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	9216 independent reflections
Radiation source: fine-focus sealed tube	6027 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ϕ and ω scans	θmax = 30.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→17
Tmin = 0.868, Tmax = 1.000	k = −17→12
35282 measured reflections	l = −18→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.148	w = 1/[σ^2(Fo^2) + (0.0707P)^2 + 0.3408P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
9216 reflections	Δρmax = 0.43 e Å^−3
420 parameters	Δρmin = −0.27 e Å^−3
18 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0064 (11)

Special details

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.

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

	x	y	z	Uiso*/Ueq
S1A	0.22130 (4)	0.14386 (4)	−0.13920 (4)	0.04965 (13)
N4A	0.46507 (12)	0.33139 (10)	−0.01828 (11)	0.0342 (3)
H4A	0.4216	0.3752	−0.0424	0.041*
N5A	0.46337 (12)	0.14316 (10)	−0.01198 (11)	0.0342 (3)
H5A	0.4189	0.0649	−0.0315	0.041*
C11A	0.67564 (15)	0.32016 (12)	0.09044 (13)	0.0328 (3)
H11A	0.7701	0.3568	0.1363	0.039*
O2A	0.65600 (12)	0.11976 (10)	0.09038 (11)	0.0484 (3)
O1A	0.65933 (11)	0.50822 (9)	0.07942 (11)	0.0445 (3)
C12A	0.60686 (14)	0.39288 (12)	0.05367 (13)	0.0323 (3)
C9A	0.39119 (15)	0.20858 (13)	−0.05281 (13)	0.0327 (3)
C10A	0.60523 (15)	0.19379 (13)	0.05971 (13)	0.0327 (3)
S1B	0.21714 (4)	0.14319 (4)	0.35860 (4)	0.05036 (14)
O1B	0.65175 (11)	0.11755 (9)	0.58234 (11)	0.0442 (3)
N5B	0.46104 (12)	0.33089 (10)	0.48262 (11)	0.0343 (3)
H5B	0.4175	0.3755	0.4624	0.041*
N4B	0.45953 (12)	0.14170 (10)	0.48133 (11)	0.0346 (3)
H4B	0.4154	0.0629	0.4581	0.042*
C10B	0.60269 (15)	0.39134 (12)	0.55173 (13)	0.0331 (3)
C11B	0.67154 (15)	0.31850 (12)	0.58652 (13)	0.0353 (3)
H11B	0.7660	0.3551	0.6323	0.042*
C12B	0.60092 (15)	0.19184 (12)	0.55379 (13)	0.0326 (3)
O2B	0.65587 (11)	0.50654 (9)	0.57604 (11)	0.0450 (3)
C9B	0.38688 (14)	0.20739 (12)	0.44495 (13)	0.0324 (3)
N1A	0.72479 (14)	0.56610 (14)	0.35783 (12)	0.0481 (4)
H1A	0.8088	0.6186	0.3967	0.058*
N3B	0.43174 (13)	0.80501 (12)	0.21446 (12)	0.0422 (3)
N3A	0.49454 (13)	0.52789 (13)	0.24923 (12)	0.0419 (3)
N2B	0.27442 (14)	0.60264 (12)	0.13434 (13)	0.0442 (3)
H2B1	0.3393	0.5810	0.1676	0.053*
H2B2	0.1916	0.5476	0.0920	0.053*
N1B	0.19843 (14)	0.75070 (13)	0.09333 (13)	0.0455 (3)
H1B	0.1172	0.6931	0.0489	0.055*
C4B	0.45403 (19)	0.92257 (16)	0.22828 (16)	0.0485 (4)
N2A	0.66125 (16)	0.72384 (15)	0.32255 (14)	0.0571 (4)
H2A1	0.5992	0.7494	0.2924	0.069*
H2A2	0.7457	0.7753	0.3611	0.069*
C2B	0.30184 (16)	0.71968 (14)	0.14815 (14)	0.0385 (3)
C4A	0.46185 (16)	0.40925 (16)	0.23724 (14)	0.0413 (4)
C2A	0.62708 (16)	0.60602 (16)	0.30979 (14)	0.0429 (4)
C6A	0.69423 (18)	0.44632 (18)	0.34655 (15)	0.0469 (4)
C5A	0.56092 (18)	0.36554 (16)	0.28518 (15)	0.0467 (4)
H5A1	0.5358	0.2820	0.2751	0.056*
C6B	0.2184 (2)	0.86975 (17)	0.10602 (17)	0.0533 (4)
C7A	0.31367 (18)	0.32529 (17)	0.16936 (17)	0.0525 (4)
H7A1	0.2689	0.3551	0.2046	0.079*
H7A2	0.3013	0.2436	0.1716	0.079*
H7A3	0.2754	0.3231	0.0882	0.079*
C7B	0.5988 (2)	1.01510 (18)	0.30179 (19)	0.0644 (6)
H7B1	0.6035	1.0920	0.3399	0.097*
H7B2	0.6371	1.0272	0.2517	0.097*
H7B3	0.6491	0.9857	0.3612	0.097*
C5B	0.3484 (2)	0.95788 (17)	0.17670 (18)	0.0582 (5)
H5B1	0.3668	1.0410	0.1906	0.070*
C8A	0.8111 (2)	0.4133 (2)	0.4030 (2)	0.0660 (6)
H8A1	0.8704	0.4393	0.3722	0.099*
H8A2	0.7774	0.3255	0.3855	0.099*
H8A3	0.8604	0.4540	0.4877	0.099*
C8B	0.0968 (2)	0.8923 (2)	0.0398 (2)	0.0824 (7)
H8B1	0.0491	0.8433	−0.0429	0.124*
H8B2	0.1249	0.9782	0.0478	0.124*
H8B3	0.0379	0.8700	0.0715	0.124*
O1W	−0.01455 (12)	0.55188 (11)	−0.10194 (11)	0.0474 (3)
H1W	−0.029 (2)	0.5809 (17)	−0.1635 (15)	0.057*
H2W	0.0148 (19)	0.4889 (15)	−0.1118 (16)	0.057*
O2W	−0.06749 (14)	0.61659 (14)	−0.29886 (15)	0.0692 (4)
H3W	−0.021 (2)	0.7009 (15)	−0.283 (2)	0.083*
H4W	−0.1612 (15)	0.594 (2)	−0.343 (2)	0.083*
O3W	1.10771 (13)	0.84477 (12)	0.71919 (12)	0.0584 (4)
H5W	1.1843 (19)	0.8408 (18)	0.7804 (17)	0.070*
H6W	1.118 (2)	0.9248 (15)	0.7402 (19)	0.070*
O4W	0.92671 (15)	0.62358 (14)	0.13032 (16)	0.0756 (5)
H7W	0.8399 (18)	0.594 (2)	0.126 (2)	0.091*
O5W	1.08949 (13)	0.84023 (13)	0.34039 (15)	0.0645 (4)
H9W	1.1768 (18)	0.844 (2)	0.362 (2)	0.077*
H10W	1.096 (2)	0.9182 (16)	0.342 (2)	0.077*
O6W	0.97011 (16)	0.75673 (18)	0.46842 (15)	0.0919 (6)
H11W	1.012 (3)	0.799 (2)	0.431 (2)	0.110*
H12W	1.031 (3)	0.791 (3)	0.5507 (14)	0.110*
H8W	0.980 (2)	0.7012 (18)	0.197 (2)	0.110*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0292 (2)	0.0349 (2)	0.0623 (3)	0.01090 (16)	0.00974 (19)	0.00785 (19)
N4A	0.0300 (6)	0.0257 (6)	0.0409 (7)	0.0124 (5)	0.0133 (5)	0.0099 (5)
N5A	0.0311 (6)	0.0241 (5)	0.0395 (7)	0.0096 (5)	0.0127 (5)	0.0112 (5)
C11A	0.0276 (7)	0.0289 (7)	0.0363 (7)	0.0096 (5)	0.0140 (6)	0.0087 (6)
O2A	0.0384 (6)	0.0316 (5)	0.0582 (7)	0.0159 (5)	0.0096 (5)	0.0170 (5)
O1A	0.0357 (6)	0.0250 (5)	0.0626 (7)	0.0110 (4)	0.0194 (5)	0.0105 (5)
C12A	0.0313 (7)	0.0262 (6)	0.0362 (7)	0.0102 (5)	0.0168 (6)	0.0079 (6)
C9A	0.0314 (7)	0.0278 (6)	0.0344 (7)	0.0113 (6)	0.0146 (6)	0.0082 (6)
C10A	0.0313 (7)	0.0306 (7)	0.0330 (7)	0.0133 (6)	0.0132 (6)	0.0120 (6)
S1B	0.0293 (2)	0.0340 (2)	0.0682 (3)	0.00908 (16)	0.0122 (2)	0.0164 (2)
O1B	0.0344 (6)	0.0288 (5)	0.0606 (7)	0.0137 (4)	0.0162 (5)	0.0171 (5)
N5B	0.0307 (6)	0.0239 (5)	0.0430 (7)	0.0106 (5)	0.0153 (6)	0.0109 (5)
N4B	0.0292 (6)	0.0217 (5)	0.0435 (7)	0.0076 (5)	0.0135 (5)	0.0100 (5)
C10B	0.0322 (7)	0.0239 (6)	0.0358 (7)	0.0077 (5)	0.0151 (6)	0.0080 (5)
C11B	0.0300 (7)	0.0261 (7)	0.0394 (8)	0.0076 (6)	0.0129 (6)	0.0098 (6)
C12B	0.0308 (7)	0.0282 (7)	0.0355 (7)	0.0113 (6)	0.0149 (6)	0.0112 (6)
O2B	0.0366 (6)	0.0227 (5)	0.0592 (7)	0.0077 (4)	0.0152 (5)	0.0112 (5)
C9B	0.0310 (7)	0.0263 (6)	0.0359 (7)	0.0096 (6)	0.0156 (6)	0.0101 (6)
N1A	0.0302 (7)	0.0619 (9)	0.0377 (7)	0.0095 (6)	0.0138 (6)	0.0132 (7)
N3B	0.0374 (7)	0.0386 (7)	0.0391 (7)	0.0046 (6)	0.0205 (6)	0.0058 (6)
N3A	0.0316 (7)	0.0461 (7)	0.0373 (7)	0.0086 (6)	0.0157 (6)	0.0100 (6)
N2B	0.0328 (7)	0.0367 (7)	0.0490 (8)	0.0074 (6)	0.0154 (6)	0.0122 (6)
N1B	0.0390 (7)	0.0409 (7)	0.0475 (8)	0.0121 (6)	0.0192 (6)	0.0119 (6)
C4B	0.0508 (10)	0.0402 (9)	0.0440 (9)	0.0051 (8)	0.0285 (8)	0.0050 (7)
N2A	0.0403 (8)	0.0513 (9)	0.0584 (10)	0.0049 (7)	0.0185 (7)	0.0168 (7)
C2B	0.0366 (8)	0.0396 (8)	0.0352 (8)	0.0098 (6)	0.0203 (7)	0.0096 (6)
C4A	0.0357 (8)	0.0485 (9)	0.0330 (8)	0.0119 (7)	0.0180 (7)	0.0089 (7)
C2A	0.0356 (8)	0.0508 (9)	0.0348 (8)	0.0098 (7)	0.0182 (7)	0.0130 (7)
C6A	0.0416 (9)	0.0626 (11)	0.0357 (8)	0.0220 (8)	0.0196 (7)	0.0150 (8)
C5A	0.0446 (9)	0.0486 (9)	0.0421 (9)	0.0175 (8)	0.0210 (8)	0.0120 (7)
C6B	0.0599 (12)	0.0463 (10)	0.0526 (10)	0.0231 (9)	0.0277 (9)	0.0158 (8)
C7A	0.0371 (9)	0.0470 (10)	0.0528 (10)	0.0057 (7)	0.0178 (8)	0.0071 (8)
C7B	0.0574 (12)	0.0426 (10)	0.0641 (12)	−0.0050 (9)	0.0316 (10)	−0.0001 (9)
C5B	0.0701 (13)	0.0371 (9)	0.0610 (12)	0.0177 (9)	0.0332 (11)	0.0122 (8)
C8A	0.0469 (11)	0.0889 (16)	0.0586 (12)	0.0337 (11)	0.0210 (10)	0.0234 (11)
C8B	0.0723 (16)	0.0709 (15)	0.0940 (18)	0.0410 (13)	0.0262 (14)	0.0299 (14)
O1W	0.0369 (6)	0.0488 (7)	0.0497 (7)	0.0152 (5)	0.0184 (6)	0.0167 (6)
O2W	0.0414 (7)	0.0579 (8)	0.0833 (11)	0.0091 (7)	0.0159 (7)	0.0352 (8)
O3W	0.0375 (7)	0.0451 (7)	0.0627 (8)	0.0117 (6)	0.0076 (6)	0.0114 (6)
O4W	0.0462 (8)	0.0538 (8)	0.1046 (13)	0.0146 (7)	0.0337 (9)	0.0004 (8)
O5W	0.0385 (7)	0.0556 (8)	0.0923 (11)	0.0180 (6)	0.0278 (7)	0.0283 (8)
O6W	0.0478 (9)	0.1074 (14)	0.0622 (10)	−0.0143 (9)	0.0198 (8)	0.0101 (10)

Geometric parameters (Å, º)

S1A—C9A	1.6760 (15)	C4B—C5B	1.396 (3)
N4A—C9A	1.3504 (18)	C4B—C7B	1.490 (3)
N4A—C12A	1.3999 (18)	N2A—C2A	1.316 (2)
N4A—H4A	0.8600	N2A—H2A1	0.8600
N5A—C9A	1.3538 (18)	N2A—H2A2	0.8600
N5A—C10A	1.4005 (18)	C4A—C5A	1.397 (2)
N5A—H5A	0.8600	C4A—C7A	1.491 (2)
C11A—C10A	1.3873 (19)	C6A—C5A	1.357 (2)
C11A—C12A	1.392 (2)	C6A—C8A	1.494 (3)
C11A—H11A	0.9300	C5A—H5A1	0.9300
O2A—C10A	1.2583 (17)	C6B—C5B	1.360 (3)
O1A—C12A	1.2576 (16)	C6B—C8B	1.484 (3)
S1B—C9B	1.6748 (15)	C7A—H7A1	0.9600
O1B—C12B	1.2556 (17)	C7A—H7A2	0.9600
N5B—C9B	1.3538 (17)	C7A—H7A3	0.9600
N5B—C10B	1.3957 (18)	C7B—H7B1	0.9600
N5B—H5B	0.8600	C7B—H7B2	0.9600
N4B—C9B	1.3490 (18)	C7B—H7B3	0.9600
N4B—C12B	1.3973 (18)	C5B—H5B1	0.9300
N4B—H4B	0.8600	C8A—H8A1	0.9600
C10B—O2B	1.2588 (16)	C8A—H8A2	0.9600
C10B—C11B	1.390 (2)	C8A—H8A3	0.9600
C11B—C12B	1.3872 (19)	C8B—H8B1	0.9600
C11B—H11B	0.9300	C8B—H8B2	0.9600
N1A—C6A	1.347 (2)	C8B—H8B3	0.9600
N1A—C2A	1.352 (2)	O1W—H1W	0.906 (14)
N1A—H1A	0.8600	O1W—H2W	0.950 (14)
N3B—C4B	1.330 (2)	O2W—H3W	0.937 (15)
N3B—C2B	1.345 (2)	O2W—H4W	0.936 (15)
N3A—C4A	1.329 (2)	O3W—H5W	0.951 (15)
N3A—C2A	1.342 (2)	O3W—H6W	0.918 (15)
N2B—C2B	1.314 (2)	O4W—H7W	0.965 (16)
N2B—H2B1	0.8600	O4W—H8W	0.979 (16)
N2B—H2B2	0.8600	O5W—H9W	0.949 (15)
N1B—C2B	1.347 (2)	O5W—H10W	0.919 (15)
N1B—C6B	1.356 (2)	O6W—H11W	0.945 (16)
N1B—H1B	0.8600	O6W—H12W	0.936 (16)
C9A—N4A—C12A	125.09 (12)	H2A1—N2A—H2A2	120.0
C9A—N4A—H4A	117.5	N2B—C2B—N3B	119.56 (15)
C12A—N4A—H4A	117.5	N2B—C2B—N1B	118.74 (14)
C9A—N5A—C10A	124.71 (12)	N3B—C2B—N1B	121.69 (15)
C9A—N5A—H5A	117.6	N3A—C4A—C5A	121.80 (15)
C10A—N5A—H5A	117.6	N3A—C4A—C7A	116.35 (15)
C10A—C11A—C12A	120.94 (13)	C5A—C4A—C7A	121.85 (16)
C10A—C11A—H11A	119.5	N2A—C2A—N3A	118.69 (16)
C12A—C11A—H11A	119.5	N2A—C2A—N1A	119.91 (15)
O1A—C12A—C11A	126.50 (14)	N3A—C2A—N1A	121.40 (16)
O1A—C12A—N4A	116.85 (12)	N1A—C6A—C5A	117.83 (16)
C11A—C12A—N4A	116.65 (12)	N1A—C6A—C8A	116.88 (17)
N4A—C9A—N5A	115.55 (12)	C5A—C6A—C8A	125.29 (19)
N4A—C9A—S1A	121.38 (11)	C6A—C5A—C4A	119.26 (17)
N5A—C9A—S1A	123.07 (11)	C6A—C5A—H5A1	120.4
O2A—C10A—C11A	126.51 (14)	C4A—C5A—H5A1	120.4
O2A—C10A—N5A	116.47 (12)	N1B—C6B—C5B	117.10 (18)
C11A—C10A—N5A	117.02 (12)	N1B—C6B—C8B	117.18 (18)
C9B—N5B—C10B	125.05 (12)	C5B—C6B—C8B	125.72 (19)
C9B—N5B—H5B	117.5	C4A—C7A—H7A1	109.5
C10B—N5B—H5B	117.5	C4A—C7A—H7A2	109.5
C9B—N4B—C12B	125.06 (12)	H7A1—C7A—H7A2	109.5
C9B—N4B—H4B	117.5	C4A—C7A—H7A3	109.5
C12B—N4B—H4B	117.5	H7A1—C7A—H7A3	109.5
O2B—C10B—C11B	126.24 (14)	H7A2—C7A—H7A3	109.5
O2B—C10B—N5B	116.87 (13)	C4B—C7B—H7B1	109.5
C11B—C10B—N5B	116.88 (12)	C4B—C7B—H7B2	109.5
C12B—C11B—C10B	120.74 (14)	H7B1—C7B—H7B2	109.5
C12B—C11B—H11B	119.6	C4B—C7B—H7B3	109.5
C10B—C11B—H11B	119.6	H7B1—C7B—H7B3	109.5
O1B—C12B—C11B	126.34 (14)	H7B2—C7B—H7B3	109.5
O1B—C12B—N4B	116.70 (12)	C6B—C5B—C4B	119.47 (17)
C11B—C12B—N4B	116.96 (12)	C6B—C5B—H5B1	120.3
N4B—C9B—N5B	115.24 (12)	C4B—C5B—H5B1	120.3
N4B—C9B—S1B	123.36 (10)	C6A—C8A—H8A1	109.5
N5B—C9B—S1B	121.40 (11)	C6A—C8A—H8A2	109.5
C6A—N1A—C2A	121.80 (14)	H8A1—C8A—H8A2	109.5
C6A—N1A—H1A	119.1	C6A—C8A—H8A3	109.5
C2A—N1A—H1A	119.1	H8A1—C8A—H8A3	109.5
C4B—N3B—C2B	117.31 (15)	H8A2—C8A—H8A3	109.5
C4A—N3A—C2A	117.90 (15)	C6B—C8B—H8B1	109.5
C2B—N2B—H2B1	120.0	C6B—C8B—H8B2	109.5
C2B—N2B—H2B2	120.0	H8B1—C8B—H8B2	109.5
H2B1—N2B—H2B2	120.0	C6B—C8B—H8B3	109.5
C2B—N1B—C6B	122.10 (15)	H8B1—C8B—H8B3	109.5
C2B—N1B—H1B	119.0	H8B2—C8B—H8B3	109.5
C6B—N1B—H1B	119.0	H1W—O1W—H2W	109.0 (15)
N3B—C4B—C5B	122.22 (16)	H3W—O2W—H4W	109.0 (17)
N3B—C4B—C7B	116.21 (18)	H5W—O3W—H6W	107.2 (16)
C5B—C4B—C7B	121.57 (17)	H7W—O4W—H8W	102.7 (17)
C2A—N2A—H2A1	120.0	H9W—O5W—H10W	106.4 (17)
C2A—N2A—H2A2	120.0	H11W—O6W—H12W	108.2 (19)

(MAMPYTBA) 2-amino-4,6-dimethoxy pyrimidin-1-ium thiobarbiturate dihydrate

Crystal data

2(C6H10N3O2)·2(C4H3N2O2S)·3(H2O)·O	Z = 1
Mr = 1321.35	F(000) = 692
Triclinic, P1	Dx = 1.432 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2941 (5) Å	Cell parameters from 6415 reflections
b = 10.9564 (4) Å	θ = 1.5–26.7°
c = 14.3656 (6) Å	µ = 0.25 mm^−1
α = 77.876 (2)°	T = 296 K
β = 86.712 (3)°	Prism, colorless
γ = 75.243 (2)°	0.12 × 0.09 × 0.07 mm
V = 1531.84 (11) Å^3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	6415 independent reflections
Radiation source: fine-focus sealed tube	4542 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ϕ and ω scans	θmax = 26.7°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→12
Tmin = 0.859, Tmax = 1.000	k = −13→13
28369 measured reflections	l = −18→16

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.139	w = 1/[σ^2(Fo^2) + (0.0668P)^2 + 0.5087P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
6415 reflections	Δρmax = 0.41 e Å^−3
417 parameters	Δρmin = −0.32 e Å^−3
9 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0038 (8)

Special details

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.

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

	x	y	z	Uiso*/Ueq
S1A	0.62398 (5)	0.53745 (5)	0.28207 (5)	0.0665 (2)
S1B	0.38626 (5)	−0.07033 (5)	0.21110 (5)	0.0617 (2)
O4A	0.16426 (13)	0.72452 (12)	0.16397 (11)	0.0518 (4)
O4B	0.84401 (13)	−0.26318 (12)	0.32988 (11)	0.0540 (4)
N4B	0.63423 (15)	−0.16166 (13)	0.27880 (11)	0.0386 (4)
H4B	0.6232	−0.2360	0.2760	0.046*
N5A	0.45814 (14)	0.40761 (13)	0.24170 (11)	0.0350 (3)
H5A	0.5226	0.3407	0.2602	0.042*
N5B	0.55031 (14)	0.05536 (13)	0.26020 (11)	0.0352 (3)
H5B	0.4854	0.1226	0.2438	0.042*
N4A	0.37497 (15)	0.62576 (14)	0.21546 (12)	0.0400 (4)
H4A	0.3865	0.7009	0.2153	0.048*
O3B	0.66901 (13)	0.18582 (12)	0.29728 (10)	0.0461 (4)
O3A	0.33801 (13)	0.27411 (12)	0.21221 (10)	0.0451 (3)
N1B	1.08012 (15)	−0.41437 (16)	0.39438 (11)	0.0424 (4)
H1B	1.0175	−0.3454	0.3772	0.051*
N1A	−0.07691 (15)	0.88129 (15)	0.10252 (11)	0.0401 (4)
H1A	−0.0152	0.8110	0.1175	0.048*
C12A	0.33997 (17)	0.38843 (16)	0.21125 (13)	0.0338 (4)
C11A	0.23570 (18)	0.49782 (16)	0.18336 (13)	0.0375 (4)
H11A	0.1551	0.4892	0.1627	0.045*
C9B	0.53068 (17)	−0.05864 (16)	0.25256 (13)	0.0363 (4)
O1A	−0.35724 (15)	1.20934 (17)	0.03581 (12)	0.0670 (5)
C11B	0.77331 (18)	−0.03703 (17)	0.31635 (13)	0.0376 (4)
H11B	0.8547	−0.0297	0.3365	0.045*
O2A	−0.19880 (16)	0.75984 (15)	0.06231 (12)	0.0622 (4)
C2B	1.05988 (19)	−0.52937 (18)	0.38824 (14)	0.0416 (4)
C10B	0.75799 (17)	−0.15709 (17)	0.31013 (13)	0.0363 (4)
N2B	0.94399 (17)	−0.53192 (16)	0.35701 (14)	0.0527 (5)
H2B1	0.9285	−0.6042	0.3532	0.063*
H2B2	0.8833	−0.4613	0.3403	0.063*
N2A	0.06135 (16)	0.99175 (16)	0.14810 (13)	0.0498 (4)
H2A1	0.0780	1.0623	0.1552	0.060*
H2A2	0.1208	0.9199	0.1634	0.060*
C10A	0.25041 (18)	0.61936 (17)	0.18594 (13)	0.0364 (4)
C12B	0.66796 (17)	0.07309 (16)	0.29267 (13)	0.0337 (4)
C6A	−0.1954 (2)	0.8781 (2)	0.06778 (14)	0.0457 (5)
C4A	−0.26112 (19)	1.1010 (2)	0.05776 (14)	0.0472 (5)
C9A	0.47834 (18)	0.52337 (16)	0.24417 (14)	0.0378 (4)
C2A	−0.05441 (18)	0.99377 (18)	0.11392 (13)	0.0383 (4)
N3A	−0.14633 (16)	1.10600 (15)	0.09026 (12)	0.0441 (4)
N3B	1.15319 (18)	−0.63971 (17)	0.41394 (13)	0.0537 (5)
O2B	1.19842 (18)	−0.28611 (19)	0.42814 (13)	0.0738 (5)
C5A	−0.2925 (2)	0.9895 (2)	0.04417 (15)	0.0538 (6)
H5A1	−0.3752	0.9912	0.0203	0.065*
O1B	1.36548 (18)	−0.7378 (2)	0.46774 (14)	0.0962 (8)
C6B	1.1975 (2)	−0.4060 (2)	0.42723 (15)	0.0540 (6)
C4B	1.2666 (2)	−0.6303 (3)	0.44431 (16)	0.0633 (7)
C5B	1.2961 (2)	−0.5169 (3)	0.45415 (17)	0.0698 (8)
H5B1	1.3782	−0.5162	0.4777	0.084*
O1W	0.08779 (17)	0.22722 (17)	0.18992 (17)	0.0776 (6)
H1W	0.1655 (15)	0.232 (3)	0.2021 (18)	0.093*
H2W	0.068 (3)	0.282 (2)	0.1410 (14)	0.093*
O2W	0.91524 (17)	0.21298 (18)	0.34902 (15)	0.0744 (5)
H3W	0.966 (2)	0.211 (3)	0.3020 (14)	0.089*
H4W	0.8406 (14)	0.206 (3)	0.3346 (18)	0.089*
O3W	−0.0610 (6)	0.4545 (3)	0.0796 (5)	0.264 (3)
H5W	−0.063 (8)	0.392 (5)	0.054 (5)	0.317*
H6W	−0.016 (7)	0.417 (6)	0.130 (3)	0.317*
O4W	1.0000	0.0000	0.5000	0.293 (5)
C7A	−0.3295 (3)	1.3262 (2)	0.0519 (2)	0.0776 (8)
H7A1	−0.3087	1.3157	0.1178	0.116*
H7A2	−0.4069	1.3968	0.0352	0.116*
H7A3	−0.2545	1.3435	0.0133	0.116*
C7B	1.3412 (4)	−0.8565 (3)	0.4518 (2)	0.1209 (16)
H7B1	1.2683	−0.8767	0.4916	0.181*
H7B2	1.4207	−0.9252	0.4670	0.181*
H7B3	1.3185	−0.8461	0.3862	0.181*
C8A	−0.3206 (3)	0.7454 (3)	0.0240 (2)	0.0843 (9)
H8A1	−0.3956	0.7734	0.0640	0.126*
H8A2	−0.3110	0.6565	0.0221	0.126*
H8A3	−0.3356	0.7967	−0.0392	0.126*
C8B	1.3190 (3)	−0.2651 (4)	0.4639 (2)	0.1065 (12)
H8B1	1.3331	−0.3096	0.5290	0.160*
H8B2	1.3082	−0.1746	0.4600	0.160*
H8B3	1.3950	−0.2974	0.4261	0.160*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0407 (3)	0.0311 (3)	0.1286 (6)	−0.0042 (2)	−0.0396 (3)	−0.0131 (3)
S1B	0.0387 (3)	0.0317 (3)	0.1153 (5)	−0.0032 (2)	−0.0358 (3)	−0.0134 (3)
O4A	0.0363 (7)	0.0300 (7)	0.0836 (11)	0.0044 (5)	−0.0199 (7)	−0.0096 (7)
O4B	0.0371 (8)	0.0286 (7)	0.0911 (11)	0.0045 (6)	−0.0232 (7)	−0.0097 (7)
N4B	0.0334 (8)	0.0230 (7)	0.0580 (10)	−0.0029 (6)	−0.0125 (7)	−0.0064 (6)
N5A	0.0266 (7)	0.0240 (7)	0.0521 (9)	−0.0004 (6)	−0.0088 (6)	−0.0078 (6)
N5B	0.0271 (7)	0.0237 (7)	0.0527 (9)	−0.0003 (6)	−0.0080 (7)	−0.0087 (6)
N4A	0.0330 (8)	0.0224 (7)	0.0632 (10)	−0.0026 (6)	−0.0139 (7)	−0.0069 (7)
O3B	0.0365 (7)	0.0277 (6)	0.0760 (10)	−0.0048 (5)	−0.0135 (7)	−0.0150 (6)
O3A	0.0348 (7)	0.0276 (6)	0.0742 (10)	−0.0039 (5)	−0.0133 (6)	−0.0143 (6)
N1B	0.0280 (8)	0.0433 (9)	0.0502 (10)	0.0015 (6)	−0.0082 (7)	−0.0072 (7)
N1A	0.0287 (8)	0.0388 (9)	0.0485 (9)	0.0000 (6)	−0.0072 (7)	−0.0079 (7)
C12A	0.0307 (9)	0.0295 (9)	0.0414 (10)	−0.0053 (7)	−0.0028 (7)	−0.0098 (7)
C11A	0.0295 (9)	0.0309 (9)	0.0515 (11)	−0.0038 (7)	−0.0108 (8)	−0.0085 (8)
C9B	0.0298 (9)	0.0275 (8)	0.0500 (11)	−0.0033 (7)	−0.0088 (8)	−0.0070 (7)
O1A	0.0397 (9)	0.0632 (11)	0.0743 (11)	0.0154 (7)	−0.0076 (8)	0.0057 (8)
C11B	0.0281 (9)	0.0330 (9)	0.0512 (11)	−0.0049 (7)	−0.0089 (8)	−0.0086 (8)
O2A	0.0512 (9)	0.0607 (10)	0.0816 (11)	−0.0166 (8)	−0.0163 (8)	−0.0218 (8)
C2B	0.0342 (10)	0.0388 (10)	0.0440 (11)	0.0023 (8)	0.0004 (8)	−0.0051 (8)
C10B	0.0280 (9)	0.0312 (9)	0.0459 (11)	−0.0005 (7)	−0.0077 (8)	−0.0060 (8)
N2B	0.0399 (10)	0.0355 (9)	0.0804 (13)	−0.0020 (7)	−0.0124 (9)	−0.0126 (8)
N2A	0.0333 (9)	0.0371 (9)	0.0769 (12)	−0.0018 (7)	−0.0142 (8)	−0.0116 (8)
C10A	0.0287 (9)	0.0303 (9)	0.0473 (11)	−0.0014 (7)	−0.0080 (8)	−0.0068 (7)
C12B	0.0293 (9)	0.0314 (9)	0.0410 (10)	−0.0070 (7)	−0.0033 (7)	−0.0085 (7)
C6A	0.0363 (10)	0.0547 (12)	0.0458 (11)	−0.0108 (9)	−0.0037 (9)	−0.0092 (9)
C4A	0.0314 (10)	0.0524 (12)	0.0447 (11)	0.0041 (9)	−0.0005 (8)	0.0014 (9)
C9A	0.0322 (9)	0.0259 (8)	0.0536 (11)	−0.0031 (7)	−0.0088 (8)	−0.0073 (8)
C2A	0.0312 (9)	0.0364 (10)	0.0429 (10)	−0.0025 (7)	−0.0006 (8)	−0.0052 (8)
N3A	0.0346 (9)	0.0384 (9)	0.0487 (10)	0.0041 (7)	−0.0010 (7)	−0.0015 (7)
N3B	0.0447 (10)	0.0464 (10)	0.0510 (11)	0.0134 (8)	0.0015 (8)	0.0014 (8)
O2B	0.0635 (11)	0.0859 (13)	0.0846 (12)	−0.0330 (10)	−0.0134 (9)	−0.0242 (10)
C5A	0.0295 (10)	0.0694 (15)	0.0550 (13)	−0.0038 (10)	−0.0105 (9)	−0.0037 (11)
O1B	0.0537 (11)	0.1101 (17)	0.0747 (12)	0.0439 (11)	−0.0022 (9)	0.0134 (11)
C6B	0.0371 (11)	0.0770 (16)	0.0489 (13)	−0.0149 (11)	−0.0031 (9)	−0.0135 (11)
C4B	0.0407 (12)	0.0749 (17)	0.0489 (13)	0.0171 (11)	0.0005 (10)	0.0050 (12)
C5B	0.0290 (11)	0.112 (2)	0.0549 (14)	−0.0004 (13)	−0.0113 (10)	−0.0039 (14)
O1W	0.0472 (10)	0.0556 (11)	0.1357 (18)	−0.0116 (8)	−0.0253 (11)	−0.0265 (10)
O2W	0.0482 (10)	0.0606 (10)	0.1214 (17)	−0.0162 (9)	−0.0180 (10)	−0.0256 (11)
O3W	0.243 (5)	0.107 (3)	0.422 (8)	−0.003 (3)	−0.231 (5)	0.001 (3)
O4W	0.332 (9)	0.176 (5)	0.342 (9)	−0.083 (5)	−0.264 (8)	0.102 (5)
C7A	0.0810 (19)	0.0482 (14)	0.0767 (18)	0.0193 (13)	0.0036 (14)	0.0027 (12)
C7B	0.137 (3)	0.072 (2)	0.088 (2)	0.066 (2)	0.018 (2)	0.0136 (17)
C8A	0.0706 (18)	0.098 (2)	0.101 (2)	−0.0378 (16)	−0.0258 (16)	−0.0294 (17)
C8B	0.089 (2)	0.153 (3)	0.107 (2)	−0.073 (2)	−0.0205 (19)	−0.032 (2)

Geometric parameters (Å, º)

S1A—C9A	1.6778 (18)	N2B—H2B1	0.8600
S1B—C9B	1.6768 (17)	N2B—H2B2	0.8600
O4A—C10A	1.254 (2)	N2A—C2A	1.308 (2)
O4B—C10B	1.258 (2)	N2A—H2A1	0.8600
N4B—C9B	1.344 (2)	N2A—H2A2	0.8600
N4B—C10B	1.391 (2)	C6A—C5A	1.359 (3)
N4B—H4B	0.8600	C4A—N3A	1.313 (3)
N5A—C9A	1.344 (2)	C4A—C5A	1.395 (3)
N5A—C12A	1.395 (2)	C2A—N3A	1.338 (2)
N5A—H5A	0.8600	N3B—C4B	1.305 (3)
N5B—C9B	1.342 (2)	O2B—C6B	1.319 (3)
N5B—C12B	1.395 (2)	O2B—C8B	1.458 (3)
N5B—H5B	0.8600	C5A—H5A1	0.9300
N4A—C9A	1.345 (2)	O1B—C4B	1.341 (3)
N4A—C10A	1.396 (2)	O1B—C7B	1.451 (5)
N4A—H4A	0.8600	C6B—C5B	1.369 (3)
O3B—C12B	1.254 (2)	C4B—C5B	1.387 (4)
O3A—C12A	1.255 (2)	C5B—H5B1	0.9300
N1B—C2B	1.350 (3)	O1W—H1W	0.846 (10)
N1B—C6B	1.353 (2)	O1W—H2W	0.820 (10)
N1B—H1B	0.8600	O2W—H3W	0.828 (10)
N1A—C2A	1.354 (2)	O2W—H4W	0.832 (9)
N1A—C6A	1.355 (2)	O3W—H5W	0.853 (10)
N1A—H1A	0.8600	O3W—H6W	0.849 (10)
C12A—C11A	1.393 (2)	C7A—H7A1	0.9600
C11A—C10A	1.386 (2)	C7A—H7A2	0.9600
C11A—H11A	0.9300	C7A—H7A3	0.9600
O1A—C4A	1.329 (2)	C7B—H7B1	0.9600
O1A—C7A	1.446 (3)	C7B—H7B2	0.9600
C11B—C10B	1.386 (2)	C7B—H7B3	0.9600
C11B—C12B	1.397 (2)	C8A—H8A1	0.9600
C11B—H11B	0.9300	C8A—H8A2	0.9600
O2A—C6A	1.323 (3)	C8A—H8A3	0.9600
O2A—C8A	1.455 (3)	C8B—H8B1	0.9600
C2B—N2B	1.307 (3)	C8B—H8B2	0.9600
C2B—N3B	1.335 (2)	C8B—H8B3	0.9600
C9B—N4B—C10B	124.93 (15)	N3A—C4A—O1A	118.9 (2)
C9B—N4B—H4B	117.5	N3A—C4A—C5A	125.20 (18)
C10B—N4B—H4B	117.5	O1A—C4A—C5A	115.91 (19)
C9A—N5A—C12A	124.61 (14)	N5A—C9A—N4A	116.05 (15)
C9A—N5A—H5A	117.7	N5A—C9A—S1A	121.40 (13)
C12A—N5A—H5A	117.7	N4A—C9A—S1A	122.55 (13)
C9B—N5B—C12B	125.00 (14)	N2A—C2A—N3A	119.60 (18)
C9B—N5B—H5B	117.5	N2A—C2A—N1A	118.53 (16)
C12B—N5B—H5B	117.5	N3A—C2A—N1A	121.87 (17)
C9A—N4A—C10A	124.94 (15)	C4A—N3A—C2A	116.52 (18)
C9A—N4A—H4A	117.5	C4B—N3B—C2B	116.2 (2)
C10A—N4A—H4A	117.5	C6B—O2B—C8B	117.2 (2)
C2B—N1B—C6B	120.96 (18)	C6A—C5A—C4A	116.23 (19)
C2B—N1B—H1B	119.5	C6A—C5A—H5A1	121.9
C6B—N1B—H1B	119.5	C4A—C5A—H5A1	121.9
C2A—N1A—C6A	120.85 (16)	C4B—O1B—C7B	117.1 (3)
C2A—N1A—H1A	119.6	O2B—C6B—N1B	112.2 (2)
C6A—N1A—H1A	119.6	O2B—C6B—C5B	129.1 (2)
O3A—C12A—C11A	126.50 (16)	N1B—C6B—C5B	118.7 (2)
O3A—C12A—N5A	116.65 (15)	N3B—C4B—O1B	118.6 (3)
C11A—C12A—N5A	116.85 (15)	N3B—C4B—C5B	125.7 (2)
C10A—C11A—C12A	120.91 (16)	O1B—C4B—C5B	115.8 (3)
C10A—C11A—H11A	119.5	C6B—C5B—C4B	116.2 (2)
C12A—C11A—H11A	119.5	C6B—C5B—H5B1	121.9
N5B—C9B—N4B	115.90 (15)	C4B—C5B—H5B1	121.9
N5B—C9B—S1B	121.64 (13)	H1W—O1W—H2W	103 (2)
N4B—C9B—S1B	122.45 (13)	H3W—O2W—H4W	109 (2)
C4A—O1A—C7A	117.30 (19)	H5W—O3W—H6W	102.3 (16)
C10B—C11B—C12B	120.79 (16)	O1A—C7A—H7A1	109.5
C10B—C11B—H11B	119.6	O1A—C7A—H7A2	109.5
C12B—C11B—H11B	119.6	H7A1—C7A—H7A2	109.5
C6A—O2A—C8A	116.7 (2)	O1A—C7A—H7A3	109.5
N2B—C2B—N3B	119.36 (19)	H7A1—C7A—H7A3	109.5
N2B—C2B—N1B	118.37 (16)	H7A2—C7A—H7A3	109.5
N3B—C2B—N1B	122.26 (19)	O1B—C7B—H7B1	109.5
O4B—C10B—C11B	127.07 (16)	O1B—C7B—H7B2	109.5
O4B—C10B—N4B	116.04 (15)	H7B1—C7B—H7B2	109.5
C11B—C10B—N4B	116.88 (15)	O1B—C7B—H7B3	109.5
C2B—N2B—H2B1	120.0	H7B1—C7B—H7B3	109.5
C2B—N2B—H2B2	120.0	H7B2—C7B—H7B3	109.5
H2B1—N2B—H2B2	120.0	O2A—C8A—H8A1	109.5
C2A—N2A—H2A1	120.0	O2A—C8A—H8A2	109.5
C2A—N2A—H2A2	120.0	H8A1—C8A—H8A2	109.5
H2A1—N2A—H2A2	120.0	O2A—C8A—H8A3	109.5
O4A—C10A—C11A	127.07 (17)	H8A1—C8A—H8A3	109.5
O4A—C10A—N4A	116.33 (15)	H8A2—C8A—H8A3	109.5
C11A—C10A—N4A	116.59 (15)	O2B—C8B—H8B1	109.5
O3B—C12B—N5B	117.02 (15)	O2B—C8B—H8B2	109.5
O3B—C12B—C11B	126.53 (16)	H8B1—C8B—H8B2	109.5
N5B—C12B—C11B	116.45 (15)	O2B—C8B—H8B3	109.5
O2A—C6A—N1A	112.06 (17)	H8B1—C8B—H8B3	109.5
O2A—C6A—C5A	128.63 (19)	H8B2—C8B—H8B3	109.5
N1A—C6A—C5A	119.31 (19)

(TMPTBA) 2,4-diamino-5-(3,4,5-trimethoxybenzyl) pyrimidine thiobarbiturate

Crystal data

C14H19N4O3·C4H3N2O2S	F(000) = 912
Mr = 434.48	Dx = 1.394 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7106 reflections
a = 7.8329 (1) Å	θ = 1.8–33.5°
b = 15.2433 (2) Å	µ = 0.20 mm^−1
c = 17.7173 (2) Å	T = 293 K
β = 101.925 (1)°	Prism, colorless
V = 2069.78 (4) Å^3	0.25 × 0.20 × 0.18 mm
Z = 4

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	7106 independent reflections
Radiation source: fine-focus sealed tube	5527 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ϕ and ω scans	θmax = 33.6°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→10
Tmin = 0.812, Tmax = 1.000	k = −22→22
26106 measured reflections	l = −24→26

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0714P)^2 + 0.4933P] where P = (Fo^2 + 2Fc^2)/3
7106 reflections	(Δ/σ)max = 0.001
274 parameters	Δρmax = 0.47 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
S1	−0.91649 (4)	0.63979 (3)	0.39412 (2)	0.04172 (11)
N6	−0.59768 (11)	0.57296 (6)	0.41678 (5)	0.02513 (18)
H6A	−0.6238	0.5482	0.4565	0.030*
N5	−0.67158 (12)	0.66354 (7)	0.31209 (6)	0.0311 (2)
H5	−0.7460	0.6980	0.2843	0.037*
C18	−0.43323 (13)	0.55622 (7)	0.40124 (6)	0.02261 (19)
C17	−0.71888 (13)	0.62558 (8)	0.37338 (6)	0.0265 (2)
C20	−0.51135 (14)	0.65167 (8)	0.28971 (7)	0.0291 (2)
C19	−0.39239 (14)	0.59496 (8)	0.33663 (6)	0.0279 (2)
H19	−0.2851	0.5835	0.3240	0.033*
O4	−0.33500 (10)	0.50467 (6)	0.44762 (5)	0.02860 (17)
O5	−0.48927 (12)	0.69141 (7)	0.23155 (6)	0.0428 (2)
N3	−0.10738 (12)	0.29534 (7)	0.29106 (6)	0.0308 (2)
N1	−0.10349 (13)	0.40017 (7)	0.38816 (6)	0.0311 (2)
H1	−0.1608	0.4356	0.4114	0.037*
C2	−0.18540 (14)	0.35767 (8)	0.32397 (6)	0.0274 (2)
N2	−0.35002 (13)	0.37965 (8)	0.29432 (7)	0.0379 (3)
H2A	−0.4062	0.3535	0.2537	0.045*
H2B	−0.4002	0.4200	0.3158	0.045*
C8	0.43076 (15)	0.24618 (8)	0.46227 (7)	0.0319 (2)
C4	0.06310 (14)	0.27955 (8)	0.31906 (7)	0.0275 (2)
N4	0.13647 (14)	0.21722 (8)	0.28440 (7)	0.0405 (3)
H4A	0.0755	0.1891	0.2460	0.049*
H4B	0.2451	0.2048	0.3003	0.049*
C5	0.16201 (14)	0.32823 (8)	0.38295 (6)	0.0273 (2)
C7	0.35679 (15)	0.31967 (8)	0.40746 (7)	0.0321 (2)
H7B	0.4013	0.3746	0.4313	0.039*
H7A	0.4036	0.3131	0.3612	0.039*
C6	0.06971 (16)	0.38685 (8)	0.41602 (7)	0.0317 (2)
H6	0.1262	0.4187	0.4587	0.038*
C13	0.35691 (17)	0.22286 (10)	0.52405 (7)	0.0380 (3)
H13	0.2509	0.2470	0.5293	0.046*
O2	0.69265 (16)	0.07344 (8)	0.62802 (6)	0.0530 (3)
O3	0.38451 (17)	0.13778 (10)	0.64255 (7)	0.0604 (3)
C12	0.44280 (19)	0.16300 (11)	0.57822 (7)	0.0404 (3)
O1	0.82140 (15)	0.10493 (9)	0.50224 (8)	0.0586 (3)
C11	0.60182 (19)	0.12694 (10)	0.57106 (8)	0.0396 (3)
C9	0.58651 (17)	0.20800 (9)	0.45330 (8)	0.0369 (3)
H9	0.6342	0.2227	0.4111	0.044*
C10	0.67100 (17)	0.14797 (10)	0.50725 (8)	0.0396 (3)
C14	0.8941 (3)	0.12222 (19)	0.43752 (15)	0.0817 (7)
H14A	0.8119	0.1065	0.3914	0.123*
H14B	0.9988	0.0884	0.4409	0.123*
H14C	0.9212	0.1835	0.4361	0.123*
C15	0.6471 (4)	−0.01655 (14)	0.61919 (14)	0.0791 (7)
H15A	0.5279	−0.0241	0.6237	0.119*
H15B	0.7217	−0.0501	0.6586	0.119*
H15C	0.6607	−0.0364	0.5694	0.119*
C16	0.2062 (3)	0.1410 (2)	0.64047 (13)	0.0836 (8)
H16A	0.1679	0.2009	0.6369	0.125*
H16B	0.1825	0.1152	0.6867	0.125*
H16C	0.1451	0.1090	0.5964	0.125*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.02336 (14)	0.0606 (2)	0.04375 (18)	0.01229 (13)	0.01290 (12)	0.02020 (15)
N6	0.0217 (4)	0.0309 (5)	0.0235 (4)	0.0036 (3)	0.0065 (3)	0.0068 (3)
N5	0.0214 (4)	0.0403 (6)	0.0320 (5)	0.0061 (4)	0.0064 (3)	0.0150 (4)
C18	0.0203 (4)	0.0244 (5)	0.0228 (4)	0.0019 (3)	0.0035 (3)	−0.0008 (4)
C17	0.0200 (4)	0.0324 (6)	0.0270 (5)	0.0020 (4)	0.0046 (4)	0.0057 (4)
C20	0.0233 (5)	0.0351 (6)	0.0295 (5)	−0.0005 (4)	0.0071 (4)	0.0080 (4)
C19	0.0222 (4)	0.0341 (6)	0.0283 (5)	0.0033 (4)	0.0074 (4)	0.0066 (4)
O4	0.0258 (4)	0.0340 (4)	0.0263 (4)	0.0094 (3)	0.0059 (3)	0.0062 (3)
O5	0.0329 (4)	0.0583 (6)	0.0397 (5)	0.0055 (4)	0.0129 (4)	0.0253 (5)
N3	0.0247 (4)	0.0360 (5)	0.0309 (5)	−0.0001 (4)	0.0040 (3)	−0.0119 (4)
N1	0.0301 (5)	0.0339 (5)	0.0288 (4)	0.0025 (4)	0.0053 (4)	−0.0106 (4)
C2	0.0256 (5)	0.0307 (6)	0.0264 (5)	−0.0020 (4)	0.0062 (4)	−0.0042 (4)
N2	0.0268 (5)	0.0470 (6)	0.0383 (5)	0.0048 (4)	0.0033 (4)	−0.0154 (5)
C8	0.0296 (5)	0.0334 (6)	0.0293 (5)	−0.0005 (4)	−0.0016 (4)	−0.0040 (4)
C4	0.0254 (5)	0.0284 (5)	0.0286 (5)	−0.0013 (4)	0.0050 (4)	−0.0053 (4)
N4	0.0282 (5)	0.0463 (7)	0.0450 (6)	0.0043 (4)	0.0027 (4)	−0.0217 (5)
C5	0.0265 (5)	0.0289 (5)	0.0250 (5)	−0.0015 (4)	0.0016 (4)	−0.0027 (4)
C7	0.0258 (5)	0.0335 (6)	0.0343 (6)	−0.0021 (4)	0.0003 (4)	−0.0014 (5)
C6	0.0318 (5)	0.0331 (6)	0.0278 (5)	−0.0008 (4)	0.0008 (4)	−0.0085 (4)
C13	0.0351 (6)	0.0454 (7)	0.0319 (6)	0.0058 (5)	0.0033 (5)	−0.0028 (5)
O2	0.0569 (7)	0.0550 (7)	0.0401 (5)	0.0092 (5)	−0.0058 (5)	0.0091 (5)
O3	0.0575 (7)	0.0898 (10)	0.0350 (5)	0.0131 (6)	0.0120 (5)	0.0151 (6)
C12	0.0427 (7)	0.0490 (8)	0.0278 (5)	0.0027 (6)	0.0035 (5)	−0.0012 (5)
O1	0.0428 (6)	0.0695 (8)	0.0649 (7)	0.0230 (5)	0.0146 (5)	0.0177 (6)
C11	0.0400 (7)	0.0418 (7)	0.0326 (6)	0.0034 (5)	−0.0025 (5)	−0.0002 (5)
C9	0.0318 (6)	0.0420 (7)	0.0356 (6)	0.0019 (5)	0.0039 (5)	0.0008 (5)
C10	0.0312 (6)	0.0430 (7)	0.0422 (7)	0.0050 (5)	0.0017 (5)	0.0006 (6)
C14	0.0545 (11)	0.115 (2)	0.0838 (15)	0.0324 (12)	0.0336 (11)	0.0292 (14)
C15	0.1123 (19)	0.0493 (11)	0.0710 (13)	0.0149 (11)	0.0075 (12)	0.0134 (10)
C16	0.0650 (13)	0.132 (2)	0.0602 (12)	0.0174 (13)	0.0292 (10)	0.0250 (13)

Geometric parameters (Å, º)

S1—C17	1.6771 (11)	C5—C6	1.3563 (17)
N6—C17	1.3544 (13)	C5—C7	1.5032 (15)
N6—C18	1.3952 (13)	C7—H7B	0.9700
N6—H6A	0.8600	C7—H7A	0.9700
N5—C17	1.3481 (14)	C6—H6	0.9300
N5—C20	1.4040 (14)	C13—C12	1.3928 (19)
N5—H5	0.8600	C13—H13	0.9300
C18—O4	1.2741 (12)	O2—C11	1.3760 (16)
C18—C19	1.3832 (15)	O2—C15	1.418 (3)
C20—O5	1.2379 (14)	O3—C12	1.3676 (18)
C20—C19	1.4093 (15)	O3—C16	1.390 (2)
C19—H19	0.9300	C12—C11	1.391 (2)
N3—C2	1.3279 (15)	O1—C10	1.3673 (17)
N3—C4	1.3466 (14)	O1—C14	1.406 (3)
N1—C2	1.3502 (14)	C11—C10	1.388 (2)
N1—C6	1.3596 (15)	C9—C10	1.3883 (19)
N1—H1	0.8600	C9—H9	0.9300
C2—N2	1.3308 (15)	C14—H14A	0.9600
N2—H2A	0.8600	C14—H14B	0.9600
N2—H2B	0.8600	C14—H14C	0.9600
C8—C13	1.3858 (19)	C15—H15A	0.9600
C8—C9	1.3901 (18)	C15—H15B	0.9600
C8—C7	1.5170 (17)	C15—H15C	0.9600
C4—N4	1.3251 (15)	C16—H16A	0.9600
C4—C5	1.4387 (15)	C16—H16B	0.9600
N4—H4A	0.8600	C16—H16C	0.9600
N4—H4B	0.8600
C17—N6—C18	124.32 (9)	C5—C7—H7A	107.6
C17—N6—H6A	117.8	C8—C7—H7A	107.6
C18—N6—H6A	117.8	H7B—C7—H7A	107.1
C17—N5—C20	125.64 (9)	C5—C6—N1	121.50 (10)
C17—N5—H5	117.2	C5—C6—H6	119.3
C20—N5—H5	117.2	N1—C6—H6	119.3
O4—C18—C19	125.80 (9)	C8—C13—C12	119.43 (12)
O4—C18—N6	116.41 (9)	C8—C13—H13	120.3
C19—C18—N6	117.78 (9)	C12—C13—H13	120.3
N5—C17—N6	115.75 (9)	C11—O2—C15	114.34 (14)
N5—C17—S1	122.73 (8)	C12—O3—C16	118.33 (14)
N6—C17—S1	121.50 (8)	O3—C12—C11	115.12 (13)
O5—C20—N5	117.31 (10)	O3—C12—C13	124.16 (14)
O5—C20—C19	127.02 (11)	C11—C12—C13	120.67 (13)
N5—C20—C19	115.67 (10)	C10—O1—C14	117.53 (14)
C18—C19—C20	120.81 (10)	O2—C11—C10	120.30 (13)
C18—C19—H19	119.6	O2—C11—C12	120.28 (14)
C20—C19—H19	119.6	C10—C11—C12	119.38 (13)
C2—N3—C4	118.52 (10)	C10—C9—C8	120.13 (13)
C2—N1—C6	119.93 (10)	C10—C9—H9	119.9
C2—N1—H1	120.0	C8—C9—H9	119.9
C6—N1—H1	120.0	O1—C10—C9	124.48 (14)
N3—C2—N2	120.21 (10)	O1—C10—C11	115.37 (13)
N3—C2—N1	122.10 (10)	C9—C10—C11	120.14 (13)
N2—C2—N1	117.69 (10)	O1—C14—H14A	109.5
C2—N2—H2A	120.0	O1—C14—H14B	109.5
C2—N2—H2B	120.0	H14A—C14—H14B	109.5
H2A—N2—H2B	120.0	O1—C14—H14C	109.5
C13—C8—C9	120.15 (12)	H14A—C14—H14C	109.5
C13—C8—C7	121.90 (11)	H14B—C14—H14C	109.5
C9—C8—C7	117.65 (12)	O2—C15—H15A	109.5
N4—C4—N3	116.71 (10)	O2—C15—H15B	109.5
N4—C4—C5	121.32 (10)	H15A—C15—H15B	109.5
N3—C4—C5	121.96 (10)	O2—C15—H15C	109.5
C4—N4—H4A	120.0	H15A—C15—H15C	109.5
C4—N4—H4B	120.0	H15B—C15—H15C	109.5
H4A—N4—H4B	120.0	O3—C16—H16A	109.5
C6—C5—C4	115.55 (10)	O3—C16—H16B	109.5
C6—C5—C7	122.15 (10)	H16A—C16—H16B	109.5
C4—C5—C7	122.14 (10)	O3—C16—H16C	109.5
C5—C7—C8	118.66 (10)	H16A—C16—H16C	109.5
C5—C7—H7B	107.6	H16B—C16—H16C	109.5
C8—C7—H7B	107.6