Solvent influence on the crystal packing of 6-amino­thio­cytosine

The crystal structures of 6-amino­thio­cytosine (systematic name: 4,6-di­amino-1,2-di­hydro­pyrimidine-2-thione, DAPMT, C₄H₆N₄S), its hemihydrate (0.5H₂O) and its di­methyl­formamide (DMF, C₃H₇NO) monosolvate were com­pared, and the influence of the type of solvent on the supra­molecular motifs was analysed. In all three crystal structures, there are two symmetry-independent mol­ecules (A and B), and these mol­ecules are connected by three relatively short and directional hydrogen bonds to form chains of alternating A and B mol­ecules. A further organization of these chains is dependent on the nature of the solvent mol­ecule. In the unsolvated form, two orientations of the neighbouring chains are observed, and similar motifs – but only one per structure – can be observed in the solvated structures. These two different motifs can be connected by two different kinds of contacts, i.e. either π–π (hemihydrate) or staple-supported S...S (DMF). In the crystal structures, the O atoms of the solvent mol­ecules are double acceptors of the same type of hydrogen bonds and bind the chains of DAPMT mol­ecules into different motifs (dimeric or infinite chains). A Hirshfeld fingerprint analysis was used for visualization and additional inter­pretation of these results.

Computing details

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2019); cell refinement: CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020) and ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015b).

4,6-Diamino-1,2-dihydropyrimidine-2-thione (1)

Crystal data

C4H6N4S	F(000) = 592
Mr = 142.19	Dx = 1.549 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 9.7038 (3) Å	Cell parameters from 6420 reflections
b = 10.5386 (1) Å	θ = 5.6–75.3°
c = 15.3898 (4) Å	µ = 3.95 mm^−1
β = 129.196 (4)°	T = 130 K
V = 1219.70 (9) Å^3	Block, colourless
Z = 8	0.02 × 0.01 × 0.01 mm

Data collection

Rigaku OD SuperNova Single source diffractometer with an Atlas detector	2498 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2411 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.027
Detector resolution: 10.5357 pixels mm^-1	θmax = 75.6°, θmin = 5.6°
ω scans	h = −10→12
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019)	k = −12→13
Tmin = 0.586, Tmax = 1.000	l = −19→17
8624 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	All H-atom parameters refined
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0546P)^2 + 0.5044P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
2498 reflections	Δρmax = 0.21 e Å^−3
211 parameters	Δρmin = −0.30 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.

Refinement. X-ray diffraction data were collected on a Rigaku OD four-circle Supernova diffractometer using monochromatic CuK_α radiation (λ = 1.54178 Å). The temperature was controlled with an Oxford Instruments Cryosystem device. The data were corrected for absorption (multi-scan) (Rigaku OD, 2018). Accurate unit-cell parameters were determined by a least-squares fit of the reflections of the highest intensity, which were chosen from the whole experiment. The calculations were mainly performed within the WinGX program system (Farrugia, 2012) and OLEX2 (Dolomanov et al., 2009). The structures were solved with SHELXT (Sheldrick, 2015a)/SIR92 (Altomare et al., 1993).

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

	x	y	z	Uiso*/Ueq
N1A	0.3943 (2)	0.38250 (16)	0.28201 (13)	0.0331 (3)
H1A	0.499 (4)	0.361 (3)	0.314 (2)	0.045 (7)*
C2A	0.3083 (2)	0.33101 (17)	0.31767 (15)	0.0301 (4)
S2A	0.41562 (6)	0.21611 (5)	0.41853 (4)	0.03527 (15)
N3A	0.1460 (2)	0.37011 (16)	0.27509 (13)	0.0349 (3)
C4A	0.0669 (2)	0.46044 (18)	0.19339 (16)	0.0359 (4)
N4A	−0.0939 (3)	0.4988 (2)	0.1556 (2)	0.0580 (6)
H4A1	−0.146 (4)	0.558 (3)	0.109 (3)	0.070 (9)*
H4A2	−0.143 (4)	0.458 (3)	0.175 (2)	0.053 (7)*
C5A	0.1479 (2)	0.51154 (19)	0.15197 (16)	0.0372 (4)
H5A	0.089 (3)	0.577 (3)	0.093 (2)	0.049 (7)*
C6A	0.3187 (2)	0.47335 (18)	0.20079 (15)	0.0343 (4)
N6A	0.4195 (3)	0.5231 (2)	0.17719 (18)	0.0496 (5)
H6A1	0.510 (4)	0.480 (3)	0.190 (2)	0.054 (7)*
H6A2	0.375 (4)	0.580 (3)	0.129 (3)	0.064 (9)*
N1B	0.0216 (2)	0.33392 (15)	0.41027 (13)	0.0316 (3)
H1B	0.055 (3)	0.336 (2)	0.373 (2)	0.044 (6)*
C2B	−0.1562 (2)	0.32697 (17)	0.35684 (15)	0.0309 (4)
S2B	−0.29893 (6)	0.31236 (5)	0.21430 (4)	0.03871 (16)
N3B	−0.2159 (2)	0.32809 (15)	0.41436 (13)	0.0321 (3)
C4B	−0.0950 (2)	0.34083 (17)	0.52799 (15)	0.0317 (4)
N4B	−0.1626 (3)	0.3427 (2)	0.58142 (17)	0.0441 (4)
H4B1	−0.268 (4)	0.322 (3)	0.543 (2)	0.054 (8)*
H4B2	−0.099 (4)	0.341 (3)	0.649 (2)	0.049 (7)*
C5B	0.0868 (2)	0.35283 (19)	0.58554 (15)	0.0331 (4)
H5B	0.170 (3)	0.364 (2)	0.663 (2)	0.041 (6)*
C6B	0.1461 (2)	0.34743 (17)	0.52414 (14)	0.0309 (4)
N6B	0.3156 (2)	0.3559 (2)	0.56732 (16)	0.0433 (4)
H6B1	0.343 (4)	0.332 (3)	0.529 (2)	0.047 (7)*
H6B2	0.394 (4)	0.350 (3)	0.637 (3)	0.054 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0254 (7)	0.0419 (8)	0.0340 (8)	0.0001 (6)	0.0197 (6)	0.0023 (6)
C2A	0.0263 (8)	0.0362 (9)	0.0300 (8)	−0.0033 (6)	0.0188 (7)	−0.0046 (7)
S2A	0.0301 (2)	0.0421 (3)	0.0359 (3)	0.00286 (17)	0.0220 (2)	0.00540 (17)
N3A	0.0283 (7)	0.0419 (8)	0.0369 (8)	0.0015 (6)	0.0218 (6)	0.0009 (6)
C4A	0.0298 (9)	0.0376 (9)	0.0384 (9)	0.0007 (7)	0.0207 (8)	−0.0002 (7)
N4A	0.0382 (10)	0.0642 (13)	0.0754 (14)	0.0178 (9)	0.0377 (10)	0.0284 (11)
C5A	0.0333 (9)	0.0373 (9)	0.0393 (10)	0.0010 (7)	0.0222 (8)	0.0035 (8)
C6A	0.0332 (9)	0.0382 (9)	0.0343 (9)	−0.0037 (7)	0.0226 (8)	−0.0012 (7)
N6A	0.0455 (10)	0.0579 (11)	0.0586 (11)	0.0066 (9)	0.0392 (10)	0.0179 (9)
N1B	0.0254 (7)	0.0434 (8)	0.0290 (7)	−0.0003 (6)	0.0186 (6)	−0.0016 (6)
C2B	0.0276 (8)	0.0343 (9)	0.0301 (9)	−0.0013 (6)	0.0179 (7)	−0.0021 (6)
S2B	0.0279 (2)	0.0592 (3)	0.0271 (2)	−0.00483 (18)	0.0164 (2)	−0.00578 (18)
N3B	0.0268 (7)	0.0424 (8)	0.0299 (7)	−0.0020 (6)	0.0192 (6)	−0.0011 (6)
C4B	0.0332 (9)	0.0346 (9)	0.0300 (8)	0.0002 (7)	0.0212 (8)	0.0014 (7)
N4B	0.0373 (10)	0.0689 (12)	0.0320 (9)	−0.0046 (8)	0.0247 (8)	−0.0011 (8)
C5B	0.0295 (9)	0.0405 (9)	0.0257 (8)	0.0013 (7)	0.0157 (7)	0.0014 (7)
C6B	0.0247 (8)	0.0340 (9)	0.0295 (8)	0.0018 (6)	0.0150 (7)	0.0006 (6)
N6B	0.0264 (8)	0.0653 (11)	0.0344 (9)	0.0024 (7)	0.0174 (8)	−0.0030 (8)

Geometric parameters (Å, º)

N1A—C6A	1.363 (2)	N1B—C2B	1.366 (2)
N1A—C2A	1.368 (2)	N1B—C6B	1.369 (2)
N1A—H1A	0.83 (3)	N1B—H1B	0.82 (3)
C2A—N3A	1.332 (2)	C2B—N3B	1.329 (2)
C2A—S2A	1.7080 (19)	C2B—S2B	1.7069 (18)
N3A—C4A	1.363 (3)	N3B—C4B	1.364 (2)
C4A—N4A	1.338 (3)	C4B—N4B	1.337 (2)
C4A—C5A	1.395 (3)	C4B—C5B	1.392 (3)
N4A—H4A1	0.84 (3)	N4B—H4B1	0.82 (3)
N4A—H4A2	0.82 (3)	N4B—H4B2	0.81 (3)
C5A—C6A	1.378 (3)	C5B—C6B	1.383 (3)
C5A—H5A	0.98 (3)	C5B—H5B	0.94 (3)
C6A—N6A	1.346 (3)	C6B—N6B	1.332 (2)
N6A—H6A1	0.89 (3)	N6B—H6B1	0.83 (3)
N6A—H6A2	0.83 (3)	N6B—H6B2	0.84 (3)
C6A—N1A—C2A	122.34 (16)	C2B—N1B—C6B	122.20 (15)
C6A—N1A—H1A	118.7 (18)	C2B—N1B—H1B	119.4 (18)
C2A—N1A—H1A	118.8 (18)	C6B—N1B—H1B	118.3 (18)
N3A—C2A—N1A	120.76 (17)	N3B—C2B—N1B	121.00 (16)
N3A—C2A—S2A	121.22 (14)	N3B—C2B—S2B	121.03 (14)
N1A—C2A—S2A	118.01 (13)	N1B—C2B—S2B	117.94 (13)
C2A—N3A—C4A	118.12 (16)	C2B—N3B—C4B	118.08 (15)
N4A—C4A—N3A	115.72 (19)	N4B—C4B—N3B	115.54 (17)
N4A—C4A—C5A	121.61 (19)	N4B—C4B—C5B	121.62 (18)
N3A—C4A—C5A	122.66 (17)	N3B—C4B—C5B	122.84 (16)
C4A—N4A—H4A1	120 (2)	C4B—N4B—H4B1	115 (2)
C4A—N4A—H4A2	118 (2)	C4B—N4B—H4B2	121.6 (19)
H4A1—N4A—H4A2	122 (3)	H4B1—N4B—H4B2	120 (3)
C6A—C5A—C4A	117.96 (18)	C6B—C5B—C4B	117.94 (16)
C6A—C5A—H5A	120.1 (15)	C6B—C5B—H5B	118.9 (15)
C4A—C5A—H5A	121.9 (15)	C4B—C5B—H5B	123.1 (15)
N6A—C6A—N1A	117.32 (17)	N6B—C6B—N1B	117.25 (17)
N6A—C6A—C5A	124.59 (19)	N6B—C6B—C5B	124.88 (17)
N1A—C6A—C5A	118.03 (17)	N1B—C6B—C5B	117.87 (16)
C6A—N6A—H6A1	121.4 (18)	C6B—N6B—H6B1	118.3 (19)
C6A—N6A—H6A2	118 (2)	C6B—N6B—H6B2	117.9 (19)
H6A1—N6A—H6A2	117 (3)	H6B1—N6B—H6B2	117 (3)
C6A—N1A—C2A—N3A	−1.3 (3)	C6B—N1B—C2B—N3B	−2.7 (3)
C6A—N1A—C2A—S2A	179.03 (14)	C6B—N1B—C2B—S2B	179.11 (14)
N1A—C2A—N3A—C4A	1.5 (3)	N1B—C2B—N3B—C4B	2.2 (3)
S2A—C2A—N3A—C4A	−178.81 (14)	S2B—C2B—N3B—C4B	−179.60 (14)
C2A—N3A—C4A—N4A	−178.28 (19)	C2B—N3B—C4B—N4B	179.34 (18)
C2A—N3A—C4A—C5A	1.0 (3)	C2B—N3B—C4B—C5B	0.1 (3)
N4A—C4A—C5A—C6A	175.5 (2)	N4B—C4B—C5B—C6B	178.74 (19)
N3A—C4A—C5A—C6A	−3.7 (3)	N3B—C4B—C5B—C6B	−2.1 (3)
C2A—N1A—C6A—N6A	175.89 (18)	C2B—N1B—C6B—N6B	−178.62 (18)
C2A—N1A—C6A—C5A	−1.5 (3)	C2B—N1B—C6B—C5B	0.6 (3)
C4A—C5A—C6A—N6A	−173.4 (2)	C4B—C5B—C6B—N6B	−179.18 (19)
C4A—C5A—C6A—N1A	3.8 (3)	C4B—C5B—C6B—N1B	1.7 (3)

4,6-Diamino-1,2-dihydropyrimidine-2-thione dimethylformamide monosolvate (1DMF)

Crystal data

C4H6N4S·C3H7NO	F(000) = 912
Mr = 215.28	Dx = 1.342 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 9.7682 (6) Å	Cell parameters from 2779 reflections
b = 13.3671 (13) Å	θ = 4.2–75.4°
c = 16.5201 (14) Å	µ = 2.55 mm^−1
β = 99.030 (7)°	T = 130 K
V = 2130.3 (3) Å^3	Prism, colourless
Z = 8	0.2 × 0.08 × 0.08 mm

Data collection

Rigaku OD SuperNova Single source diffractometer with an Atlas detector	3792 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	2837 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.059
Detector resolution: 10.5357 pixels mm^-1	θmax = 67.4°, θmin = 4.3°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019)	k = −15→15
Tmin = 0.390, Tmax = 1.000	l = −19→19
9241 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.087	H-atom parameters constrained
wR(F^2) = 0.224	w = 1/[σ^2(Fo^2) + (0.0945P)^2 + 3.8846P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
3792 reflections	Δρmax = 0.93 e Å^−3
257 parameters	Δρmin = −0.46 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.

Refinement. X-ray diffraction data were collected on a Rigaku OD four-circle Supernova diffractometer using monochromatic CuK_α radiation (λ = 1.54178 Å). The temperature was controlled with an Oxford Instruments Cryosystem device. The data were corrected for absorption (multi-scan) (Rigaku OD, 2018). Accurate unit-cell parameters were determined by a least-squares fit of the reflections of the highest intensity, which were chosen from the whole experiment. The calculations were mainly performed within the WinGX program system (Farrugia, 2012) and OLEX2 (Dolomanov et al., 2009). The structures were solved with SHELXT (Sheldrick, 2015a)/SIR92 (Altomare et al., 1993).

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

	x	y	z	Uiso*/Ueq
N1A	0.9079 (4)	0.5445 (3)	0.6476 (2)	0.0375 (8)
H1A	0.8355	0.5730	0.6636	0.045*
C2A	1.0337 (5)	0.5918 (4)	0.6630 (3)	0.0373 (10)
S2A	1.04095 (11)	0.70211 (9)	0.71543 (7)	0.0401 (3)
N3A	1.1453 (4)	0.5513 (3)	0.6395 (2)	0.0364 (8)
C4A	1.1313 (5)	0.4621 (4)	0.5988 (3)	0.0368 (10)
N4A	1.2455 (4)	0.4249 (3)	0.5747 (3)	0.0431 (9)
H4A1	1.3243	0.4578	0.5854	0.052*
H4A2	1.2417	0.3676	0.5483	0.052*
C5A	1.0056 (5)	0.4101 (4)	0.5833 (3)	0.0380 (10)
H5A	0.9992	0.3468	0.5569	0.046*
C6A	0.8911 (5)	0.4544 (4)	0.6080 (3)	0.0380 (10)
N6A	0.7637 (4)	0.4126 (3)	0.5972 (3)	0.0424 (9)
H6A1	0.6949	0.4433	0.6153	0.051*
H6A2	0.7495	0.3547	0.5719	0.051*
N1B	0.4283 (4)	0.6223 (3)	0.7221 (2)	0.0381 (9)
H1B	0.3452	0.6103	0.6947	0.046*
C2B	0.5422 (5)	0.6145 (4)	0.6812 (3)	0.0382 (10)
S2B	0.51462 (11)	0.58862 (10)	0.57953 (7)	0.0423 (3)
N3B	0.6699 (4)	0.6287 (3)	0.7227 (2)	0.0378 (9)
C4B	0.6842 (4)	0.6528 (4)	0.8036 (3)	0.0367 (10)
N4B	0.8149 (4)	0.6627 (4)	0.8421 (2)	0.0441 (10)
H4B1	0.8845	0.6536	0.8149	0.053*
H4B2	0.8310	0.6782	0.8945	0.053*
C5B	0.5716 (5)	0.6655 (4)	0.8457 (3)	0.0405 (10)
H5B	0.5847	0.6855	0.9015	0.049*
C6B	0.4403 (4)	0.6477 (3)	0.8028 (3)	0.0351 (9)
N6B	0.3238 (4)	0.6506 (3)	0.8357 (2)	0.0416 (9)
H6B1	0.2438	0.6364	0.8055	0.050*
H6B2	0.3272	0.6667	0.8877	0.050*
N1C	0.8201 (5)	0.6217 (3)	1.1134 (3)	0.0455 (10)
C1C	0.7863 (5)	0.7076 (4)	1.0751 (3)	0.0413 (11)
H1C	0.7373	0.7549	1.1026	0.050*
O1C	0.8125 (4)	0.7314 (3)	1.0077 (2)	0.0477 (8)
C11C	0.9107 (7)	0.5506 (5)	1.0805 (5)	0.0693 (17)
H11A	1.0030	0.5525	1.1137	0.104*
H11B	0.9176	0.5686	1.0238	0.104*
H11C	0.8721	0.4831	1.0819	0.104*
C12C	0.7969 (7)	0.6057 (5)	1.1970 (3)	0.0619 (16)
H12A	0.7400	0.6602	1.2133	0.093*
H12B	0.8862	0.6042	1.2335	0.093*
H12C	0.7489	0.5419	1.2005	0.093*
N1D	0.6580 (4)	0.1397 (3)	0.3952 (3)	0.0459 (10)
C1D	0.7381 (5)	0.2080 (4)	0.4386 (3)	0.0454 (11)
H1D	0.7926	0.2500	0.4098	0.054*
O1D	0.7467 (4)	0.2207 (3)	0.5124 (2)	0.0492 (9)
C11D	0.5673 (7)	0.0796 (5)	0.4370 (4)	0.0662 (17)
H11D	0.5084	0.1235	0.4643	0.099*
H11E	0.6232	0.0372	0.4779	0.099*
H11F	0.5090	0.0373	0.3971	0.099*
C12D	0.6548 (6)	0.1259 (5)	0.3083 (3)	0.0548 (14)
H12D	0.7294	0.1650	0.2903	0.082*
H12E	0.5652	0.1485	0.2788	0.082*
H12F	0.6676	0.0549	0.2967	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0309 (18)	0.041 (2)	0.042 (2)	0.0022 (16)	0.0096 (14)	−0.0019 (17)
C2A	0.034 (2)	0.045 (3)	0.034 (2)	−0.0052 (19)	0.0078 (16)	0.0072 (19)
S2A	0.0333 (5)	0.0423 (7)	0.0462 (6)	−0.0012 (4)	0.0114 (4)	−0.0045 (5)
N3A	0.0290 (17)	0.044 (2)	0.0380 (19)	0.0019 (16)	0.0112 (14)	0.0009 (17)
C4A	0.034 (2)	0.044 (3)	0.034 (2)	0.0019 (19)	0.0098 (16)	−0.0002 (19)
N4A	0.0347 (19)	0.045 (2)	0.052 (2)	−0.0014 (17)	0.0145 (16)	−0.0098 (19)
C5A	0.034 (2)	0.043 (3)	0.039 (2)	0.0003 (19)	0.0098 (17)	−0.0008 (19)
C6A	0.035 (2)	0.044 (3)	0.036 (2)	0.0029 (19)	0.0073 (16)	−0.0005 (19)
N6A	0.0336 (19)	0.043 (2)	0.052 (2)	−0.0062 (17)	0.0110 (16)	−0.0083 (18)
N1B	0.0277 (17)	0.051 (2)	0.0377 (19)	−0.0002 (16)	0.0108 (14)	−0.0004 (17)
C2B	0.033 (2)	0.041 (3)	0.043 (2)	0.0002 (19)	0.0133 (18)	−0.003 (2)
S2B	0.0337 (6)	0.0582 (8)	0.0367 (6)	−0.0020 (5)	0.0105 (4)	−0.0061 (5)
N3B	0.0291 (18)	0.045 (2)	0.041 (2)	−0.0028 (16)	0.0107 (14)	−0.0021 (17)
C4B	0.031 (2)	0.041 (3)	0.039 (2)	−0.0059 (18)	0.0102 (17)	0.0000 (19)
N4B	0.0331 (19)	0.063 (3)	0.038 (2)	−0.0018 (18)	0.0094 (15)	−0.0063 (19)
C5B	0.035 (2)	0.052 (3)	0.035 (2)	−0.003 (2)	0.0084 (17)	−0.003 (2)
C6B	0.032 (2)	0.033 (2)	0.043 (2)	−0.0020 (17)	0.0129 (17)	0.0002 (18)
N6B	0.0344 (19)	0.054 (3)	0.039 (2)	0.0004 (17)	0.0113 (15)	−0.0063 (18)
N1C	0.052 (2)	0.043 (2)	0.042 (2)	−0.0022 (19)	0.0091 (17)	0.0006 (18)
C1C	0.045 (2)	0.041 (3)	0.039 (2)	−0.002 (2)	0.0071 (18)	−0.001 (2)
O1C	0.058 (2)	0.049 (2)	0.0372 (18)	0.0023 (17)	0.0116 (14)	0.0020 (15)
C11C	0.066 (4)	0.052 (4)	0.093 (5)	0.012 (3)	0.023 (3)	0.010 (3)
C12C	0.088 (4)	0.050 (3)	0.046 (3)	−0.015 (3)	0.006 (3)	0.006 (3)
N1D	0.052 (2)	0.044 (2)	0.046 (2)	−0.0093 (19)	0.0193 (18)	−0.0008 (18)
C1D	0.048 (3)	0.045 (3)	0.046 (3)	−0.010 (2)	0.018 (2)	0.001 (2)
O1D	0.059 (2)	0.050 (2)	0.0416 (18)	−0.0102 (17)	0.0167 (15)	−0.0022 (16)
C11D	0.072 (4)	0.069 (4)	0.061 (3)	−0.032 (3)	0.020 (3)	−0.006 (3)
C12D	0.069 (3)	0.048 (3)	0.050 (3)	−0.017 (3)	0.015 (2)	−0.005 (2)

Geometric parameters (Å, º)

N1A—C6A	1.368 (6)	C5B—H5B	0.9500
N1A—C2A	1.371 (6)	C6B—N6B	1.337 (6)
N1A—H1A	0.8800	N6B—H6B1	0.8800
C2A—N3A	1.329 (6)	N6B—H6B2	0.8800
C2A—S2A	1.706 (5)	N1C—C1C	1.328 (7)
N3A—C4A	1.365 (6)	N1C—C12C	1.449 (7)
C4A—N4A	1.337 (6)	N1C—C11C	1.460 (8)
C4A—C5A	1.399 (7)	C1C—O1C	1.224 (6)
N4A—H4A1	0.8800	C1C—H1C	0.9500
N4A—H4A2	0.8800	C11C—H11A	0.9800
C5A—C6A	1.381 (6)	C11C—H11B	0.9800
C5A—H5A	0.9500	C11C—H11C	0.9800
C6A—N6A	1.350 (6)	C12C—H12A	0.9800
N6A—H6A1	0.8800	C12C—H12B	0.9800
N6A—H6A2	0.8800	C12C—H12C	0.9800
N1B—C6B	1.363 (6)	N1D—C1D	1.336 (7)
N1B—C2B	1.393 (6)	N1D—C12D	1.444 (7)
N1B—H1B	0.8800	N1D—C11D	1.448 (7)
C2B—N3B	1.340 (6)	C1D—O1D	1.221 (6)
C2B—S2B	1.694 (5)	C1D—H1D	0.9500
N3B—C4B	1.360 (6)	C11D—H11D	0.9800
C4B—N4B	1.340 (6)	C11D—H11E	0.9800
C4B—C5B	1.401 (6)	C11D—H11F	0.9800
N4B—H4B1	0.8800	C12D—H12D	0.9800
N4B—H4B2	0.8800	C12D—H12E	0.9800
C5B—C6B	1.385 (6)	C12D—H12F	0.9800
C6A—N1A—C2A	122.1 (4)	N1B—C6B—C5B	118.3 (4)
C6A—N1A—H1A	118.9	C6B—N6B—H6B1	120.0
C2A—N1A—H1A	118.9	C6B—N6B—H6B2	120.0
N3A—C2A—N1A	120.7 (5)	H6B1—N6B—H6B2	120.0
N3A—C2A—S2A	122.0 (4)	C1C—N1C—C12C	121.1 (5)
N1A—C2A—S2A	117.2 (4)	C1C—N1C—C11C	120.4 (5)
C2A—N3A—C4A	118.5 (4)	C12C—N1C—C11C	117.0 (5)
N4A—C4A—N3A	116.6 (4)	O1C—C1C—N1C	125.9 (5)
N4A—C4A—C5A	120.7 (5)	O1C—C1C—H1C	117.1
N3A—C4A—C5A	122.7 (4)	N1C—C1C—H1C	117.1
C4A—N4A—H4A1	120.0	N1C—C11C—H11A	109.5
C4A—N4A—H4A2	120.0	N1C—C11C—H11B	109.5
H4A1—N4A—H4A2	120.0	H11A—C11C—H11B	109.5
C6A—C5A—C4A	117.5 (5)	N1C—C11C—H11C	109.5
C6A—C5A—H5A	121.3	H11A—C11C—H11C	109.5
C4A—C5A—H5A	121.3	H11B—C11C—H11C	109.5
N6A—C6A—N1A	117.8 (4)	N1C—C12C—H12A	109.5
N6A—C6A—C5A	123.8 (5)	N1C—C12C—H12B	109.5
N1A—C6A—C5A	118.5 (4)	H12A—C12C—H12B	109.5
C6A—N6A—H6A1	120.0	N1C—C12C—H12C	109.5
C6A—N6A—H6A2	120.0	H12A—C12C—H12C	109.5
H6A1—N6A—H6A2	120.0	H12B—C12C—H12C	109.5
C6B—N1B—C2B	122.7 (4)	C1D—N1D—C12D	122.7 (4)
C6B—N1B—H1B	118.6	C1D—N1D—C11D	118.3 (4)
C2B—N1B—H1B	118.6	C12D—N1D—C11D	119.0 (5)
N3B—C2B—N1B	119.4 (4)	O1D—C1D—N1D	124.9 (5)
N3B—C2B—S2B	121.8 (3)	O1D—C1D—H1D	117.5
N1B—C2B—S2B	118.8 (3)	N1D—C1D—H1D	117.5
C2B—N3B—C4B	118.8 (4)	N1D—C11D—H11D	109.5
N4B—C4B—N3B	115.6 (4)	N1D—C11D—H11E	109.5
N4B—C4B—C5B	121.1 (4)	H11D—C11D—H11E	109.5
N3B—C4B—C5B	123.2 (4)	N1D—C11D—H11F	109.5
C4B—N4B—H4B1	120.0	H11D—C11D—H11F	109.5
C4B—N4B—H4B2	120.0	H11E—C11D—H11F	109.5
H4B1—N4B—H4B2	120.0	N1D—C12D—H12D	109.5
C6B—C5B—C4B	117.5 (4)	N1D—C12D—H12E	109.5
C6B—C5B—H5B	121.3	H12D—C12D—H12E	109.5
C4B—C5B—H5B	121.3	N1D—C12D—H12F	109.5
N6B—C6B—N1B	117.2 (4)	H12D—C12D—H12F	109.5
N6B—C6B—C5B	124.4 (4)	H12E—C12D—H12F	109.5
C6A—N1A—C2A—N3A	0.2 (7)	N1B—C2B—N3B—C4B	−1.5 (7)
C6A—N1A—C2A—S2A	−178.2 (3)	S2B—C2B—N3B—C4B	177.7 (4)
N1A—C2A—N3A—C4A	0.9 (6)	C2B—N3B—C4B—N4B	177.8 (5)
S2A—C2A—N3A—C4A	179.1 (3)	C2B—N3B—C4B—C5B	−1.3 (8)
C2A—N3A—C4A—N4A	178.6 (4)	N4B—C4B—C5B—C6B	−175.9 (5)
C2A—N3A—C4A—C5A	−2.3 (7)	N3B—C4B—C5B—C6B	3.1 (8)
N4A—C4A—C5A—C6A	−178.3 (4)	C2B—N1B—C6B—N6B	−178.6 (5)
N3A—C4A—C5A—C6A	2.7 (7)	C2B—N1B—C6B—C5B	−0.7 (7)
C2A—N1A—C6A—N6A	178.6 (4)	C4B—C5B—C6B—N6B	175.7 (5)
C2A—N1A—C6A—C5A	0.2 (7)	C4B—C5B—C6B—N1B	−2.1 (7)
C4A—C5A—C6A—N6A	−179.8 (4)	C12C—N1C—C1C—O1C	173.3 (5)
C4A—C5A—C6A—N1A	−1.6 (7)	C11C—N1C—C1C—O1C	8.0 (8)
C6B—N1B—C2B—N3B	2.5 (7)	C12D—N1D—C1D—O1D	−178.1 (5)
C6B—N1B—C2B—S2B	−176.6 (4)	C11D—N1D—C1D—O1D	4.0 (9)