6-Amino-1,3-dimethyl-5-[(E)-2-(methyl-sulfan-yl)benzyl-idene-amino]-pyrimidine-2,4(1H,3H)-dione-1,3,7,9-tetra-methyl-pyrimido[5,4-g]pteridine-2,4,6,8-tetrone (1/1).

In the title co-crystal, C(12)H(12)N(6)O(4)·C(14)H(16)N(4)O(2)S, both mol-ecules are essentially planar [maximum deviations = 0.129 (1) and 0.097 (1) Å, respectively]. The tricyclic and Schiff base mol-ecules are alternately stacked along the a axis and are linked by π-π inter-actions with centroid-centroid distances of 3.5170 (16) and 3.6576 (17) Å. An intra-molecular C-H⋯O hydrogen bond and a C-H⋯S contact occur in the Schiff base molecule. In the crystal, N-H⋯O, N-H⋯N and C-H⋯O hydrogen bonds lead to the formation of a three-dimensional network.

Related literature

For the crystal structure of a Schiff base derived from 5,6-diamino-1,3-dimethyl­pyrimidine-2,4(1H,3H)-dione and pico­lin­aldehyde, see: Booysen et al. (2011a ▶). For the crystal structure of the title Schiff base, see: Booysen et al. (2011b ▶). For the crystal structure of the title tricyclic compound, see: Booysen et al. (2008 ▶). For details of the use of the Schiff base N-(2-amino­benzyl­idene)-5-amino-1,3-dimethyl­pyrimidine-2,4(1H,3H)-dione as a che­lating ligand towards rhenium, see: Mayer et al. (2010 ▶). For applications of Schiff base ligands, see: Kumar et al.. 2009 ▶.

Experimental

Crystal data

C12H12N6O4·C14H16N4O2S

M = 608.64

Monoclinic,

a = 6.8501 (9) Å

b = 25.594 (4) Å

c = 15.284 (2) Å

β = 99.315 (5)°

V = 2644.3 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 100 K

0.30 × 0.05 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2010 ▶) T min = 0.946, T max = 0.991

14953 measured reflections

5846 independent reflections

4076 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.171

S = 1.01

5846 reflections

403 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT-Plus (Bruker, 2010 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: WinGX (Farrugia, 1999 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812029716/rz2778sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029716/rz2778Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029716/rz2778Isup3.cml

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

C12H12N6O4·C14H16N4O2S	F(000) = 1272
Mr = 608.64	Dx = 1.529 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4076 reflections
a = 6.8501 (9) Å	θ = 1.6–27.3°
b = 25.594 (4) Å	µ = 0.19 mm−1
c = 15.284 (2) Å	T = 100 K
β = 99.315 (5)°	Needle, yellow
V = 2644.3 (7) Å3	0.30 × 0.05 × 0.05 mm
Z = 4

Bruker APEXII CCD diffractometer	5846 independent reflections
Radiation source: fine-focus sealed tube	4076 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
ω and φ scans	θmax = 27.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker 2010)	h = −4→8
Tmin = 0.946, Tmax = 0.991	k = −32→25
14953 measured reflections	l = −19→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0805P)2 + 2.8029P] where P = (Fo2 + 2Fc2)/3
5846 reflections	(Δ/σ)max = 0.021
403 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.72820 (11)	0.31430 (3)	0.09858 (5)	0.01445 (19)
N1A	0.7048 (4)	0.19781 (9)	0.29893 (16)	0.0137 (5)
C6B	0.3512 (4)	0.38704 (11)	0.29375 (18)	0.0122 (6)
C10A	0.5483 (4)	0.04004 (11)	0.24893 (18)	0.0117 (6)
O1B	0.1720 (3)	0.16717 (9)	0.27878 (15)	0.0216 (5)
C9A	0.6023 (4)	0.12732 (11)	0.18728 (19)	0.0123 (6)
O2B	0.1935 (3)	0.26945 (8)	0.03637 (13)	0.0185 (5)
C2B	0.2047 (4)	0.26570 (12)	0.11659 (19)	0.0138 (6)
N3A	0.5985 (4)	0.06106 (9)	0.33332 (15)	0.0130 (5)
O3A	0.4773 (3)	0.51453 (8)	0.37187 (14)	0.0226 (5)
N2B	0.3985 (4)	0.42849 (10)	0.35067 (15)	0.0141 (5)
O4A	0.3461 (3)	0.45658 (8)	0.08667 (13)	0.0204 (5)
N1B	0.4176 (4)	0.48549 (10)	0.22915 (16)	0.0140 (5)
C12A	0.5942 (5)	0.02564 (12)	0.4084 (2)	0.0200 (7)
H2'1	0.5327	−0.0075	0.3869	0.030*
H2'2	0.5174	0.0416	0.4502	0.030*
H2'3	0.7296	0.0191	0.4384	0.030*
N4A	0.5536 (3)	0.07345 (9)	0.17905 (15)	0.0130 (5)
N6B	0.1685 (4)	0.21905 (10)	0.15727 (16)	0.0154 (5)
N3B	0.2817 (3)	0.35639 (10)	0.14445 (15)	0.0130 (5)
O2A	0.5003 (3)	−0.00589 (8)	0.23777 (13)	0.0160 (5)
C12B	0.4159 (5)	0.42088 (13)	0.44709 (19)	0.0194 (7)
H8A1	0.3139	0.3964	0.4595	0.029*
H8A2	0.3985	0.4545	0.4756	0.029*
H8A3	0.5470	0.4067	0.4704	0.029*
C13B	0.2677 (5)	0.24331 (13)	0.39999 (19)	0.0219 (7)
H5A1	0.3921	0.2248	0.4201	0.033*
H5A2	0.1566	0.2220	0.4125	0.033*
H5A3	0.2684	0.2767	0.4313	0.033*
C13A	0.5062 (5)	0.05017 (12)	0.09037 (18)	0.0176 (7)
H1'1	0.5963	0.0210	0.0854	0.026*
H1'2	0.5212	0.0766	0.0455	0.026*
H1'3	0.3695	0.0374	0.0810	0.026*
O1A	0.5986 (3)	0.15304 (8)	0.11890 (13)	0.0185 (5)
N4B	0.3251 (4)	0.34063 (9)	0.32905 (15)	0.0125 (5)
C5B	0.3307 (4)	0.39547 (11)	0.20163 (18)	0.0124 (6)
N2A	0.7067 (4)	0.12816 (11)	0.43183 (17)	0.0173 (6)
N5B	0.2466 (4)	0.25296 (10)	0.30381 (15)	0.0146 (5)
C11A	0.6542 (4)	0.11251 (11)	0.34771 (18)	0.0118 (6)
C3A	0.8699 (4)	0.38866 (12)	0.33665 (19)	0.0162 (6)
H3	0.9055	0.4228	0.3579	0.019*
C7A	0.7108 (4)	0.23495 (11)	0.24313 (18)	0.0128 (6)
H7	0.6804	0.2280	0.1814	0.015*
C5A	0.7767 (4)	0.32939 (11)	0.21317 (18)	0.0118 (6)
C8B	0.3641 (4)	0.44696 (12)	0.16650 (19)	0.0146 (6)
C7B	0.4332 (4)	0.47830 (12)	0.32141 (19)	0.0151 (6)
C1B	0.1943 (4)	0.20993 (12)	0.2492 (2)	0.0164 (6)
C8A	0.6539 (4)	0.14645 (11)	0.27595 (18)	0.0116 (6)
C2A	0.8602 (4)	0.34814 (12)	0.39644 (19)	0.0153 (6)
H4	0.8905	0.3544	0.4584	0.018*
C6A	0.7642 (4)	0.28798 (11)	0.27399 (18)	0.0126 (6)
C4A	0.8276 (4)	0.37937 (11)	0.24528 (19)	0.0131 (6)
H2	0.8336	0.4073	0.2049	0.016*
C1A	0.8059 (4)	0.29850 (12)	0.36480 (19)	0.0143 (6)
H5	0.7968	0.2711	0.4058	0.017*
C3B	0.2553 (4)	0.30973 (11)	0.17811 (18)	0.0116 (6)
C4B	0.2761 (4)	0.30162 (11)	0.27104 (18)	0.0125 (6)
C11B	0.4385 (5)	0.53951 (12)	0.1995 (2)	0.0190 (7)
H9A1	0.4701	0.5394	0.1392	0.028*
H9A2	0.5452	0.5568	0.2396	0.028*
H9A3	0.3142	0.5584	0.2000	0.028*
C10B	0.1018 (5)	0.17369 (12)	0.1007 (2)	0.0211 (7)
H6A1	−0.0311	0.1634	0.1100	0.032*
H6A2	0.1934	0.1445	0.1163	0.032*
H6A3	0.0989	0.1830	0.0384	0.032*
C14A	0.7605 (5)	0.37598 (12)	0.0459 (2)	0.0202 (7)
H20A	0.6672	0.4016	0.0631	0.030*
H20B	0.7358	0.3715	−0.0186	0.030*
H20C	0.8961	0.3884	0.0647	0.030*
H101	0.732 (5)	0.1605 (14)	0.439 (2)	0.020 (9)*
H102	0.737 (6)	0.1055 (16)	0.482 (3)	0.040 (11)*

	U11	U22	U33	U12	U13	U23
S1	0.0197 (4)	0.0154 (4)	0.0089 (4)	−0.0009 (3)	0.0042 (3)	−0.0001 (3)
N1A	0.0140 (13)	0.0124 (13)	0.0152 (13)	−0.0009 (10)	0.0035 (9)	−0.0011 (10)
C6B	0.0082 (13)	0.0170 (15)	0.0112 (14)	0.0029 (11)	0.0010 (10)	−0.0040 (11)
C10A	0.0116 (14)	0.0135 (15)	0.0106 (14)	0.0021 (11)	0.0035 (10)	0.0014 (11)
O1B	0.0240 (12)	0.0175 (12)	0.0230 (12)	0.0009 (9)	0.0031 (9)	0.0015 (9)
C9A	0.0106 (14)	0.0120 (15)	0.0148 (15)	0.0000 (11)	0.0039 (10)	0.0015 (11)
O2B	0.0192 (11)	0.0264 (12)	0.0095 (10)	−0.0005 (9)	0.0011 (8)	−0.0064 (9)
C2B	0.0092 (14)	0.0191 (16)	0.0130 (15)	0.0007 (11)	0.0015 (10)	−0.0030 (11)
N3A	0.0164 (13)	0.0147 (13)	0.0080 (12)	−0.0017 (10)	0.0022 (9)	0.0020 (9)
O3A	0.0314 (13)	0.0205 (12)	0.0154 (12)	−0.0035 (10)	0.0022 (9)	−0.0066 (9)
N2B	0.0186 (13)	0.0175 (13)	0.0054 (12)	0.0016 (10)	−0.0005 (9)	−0.0038 (9)
O4A	0.0287 (13)	0.0236 (12)	0.0087 (11)	−0.0002 (10)	0.0024 (9)	0.0020 (9)
N1B	0.0134 (13)	0.0171 (13)	0.0116 (13)	−0.0026 (10)	0.0025 (9)	−0.0022 (10)
C12A	0.0311 (18)	0.0174 (16)	0.0118 (15)	−0.0057 (13)	0.0042 (12)	0.0035 (12)
N4A	0.0159 (13)	0.0142 (13)	0.0087 (12)	0.0000 (10)	0.0008 (9)	−0.0007 (9)
N6B	0.0156 (13)	0.0164 (13)	0.0144 (13)	−0.0020 (10)	0.0031 (9)	−0.0062 (10)
N3B	0.0108 (12)	0.0188 (13)	0.0093 (12)	0.0014 (10)	0.0016 (9)	−0.0030 (10)
O2A	0.0217 (12)	0.0123 (11)	0.0137 (11)	−0.0012 (9)	0.0021 (8)	0.0003 (8)
C12B	0.0272 (17)	0.0241 (17)	0.0065 (14)	0.0013 (14)	0.0013 (12)	−0.0031 (12)
C13B	0.0320 (19)	0.0237 (17)	0.0088 (15)	0.0002 (14)	−0.0002 (12)	0.0033 (12)
C13A	0.0262 (17)	0.0153 (16)	0.0099 (15)	−0.0023 (13)	−0.0010 (12)	−0.0026 (12)
O1A	0.0265 (12)	0.0181 (12)	0.0104 (11)	−0.0025 (9)	0.0016 (9)	0.0019 (8)
N4B	0.0140 (12)	0.0161 (13)	0.0072 (12)	0.0031 (10)	0.0015 (9)	−0.0021 (9)
C5B	0.0097 (14)	0.0194 (16)	0.0076 (14)	0.0019 (11)	0.0000 (10)	−0.0028 (11)
N2A	0.0289 (15)	0.0148 (15)	0.0081 (13)	−0.0034 (11)	0.0021 (10)	0.0000 (10)
N5B	0.0184 (13)	0.0153 (13)	0.0095 (12)	0.0032 (10)	0.0004 (9)	−0.0008 (10)
C11A	0.0109 (14)	0.0122 (14)	0.0129 (14)	0.0015 (11)	0.0043 (10)	−0.0006 (11)
C3A	0.0167 (15)	0.0154 (15)	0.0175 (16)	−0.0018 (12)	0.0053 (12)	−0.0036 (12)
C7A	0.0130 (14)	0.0180 (16)	0.0074 (13)	0.0006 (12)	0.0019 (10)	0.0002 (11)
C5A	0.0091 (14)	0.0148 (15)	0.0124 (14)	0.0004 (11)	0.0043 (10)	−0.0007 (11)
C8B	0.0122 (14)	0.0202 (16)	0.0112 (15)	0.0028 (12)	0.0012 (11)	−0.0030 (12)
C7B	0.0128 (15)	0.0207 (16)	0.0114 (15)	0.0016 (12)	0.0009 (11)	−0.0046 (12)
C1B	0.0114 (15)	0.0189 (17)	0.0185 (16)	0.0023 (12)	0.0014 (11)	−0.0025 (12)
C8A	0.0135 (14)	0.0132 (15)	0.0086 (14)	0.0017 (11)	0.0034 (10)	0.0004 (11)
C2A	0.0155 (15)	0.0185 (16)	0.0123 (15)	−0.0018 (12)	0.0041 (11)	−0.0016 (12)
C6A	0.0106 (14)	0.0139 (15)	0.0139 (15)	0.0018 (11)	0.0041 (11)	0.0013 (11)
C4A	0.0132 (14)	0.0135 (15)	0.0129 (14)	0.0010 (11)	0.0030 (11)	0.0028 (11)
C1A	0.0132 (14)	0.0187 (16)	0.0118 (14)	0.0001 (12)	0.0045 (11)	0.0025 (12)
C3B	0.0090 (13)	0.0178 (16)	0.0080 (14)	0.0031 (11)	0.0016 (10)	−0.0033 (11)
C4B	0.0093 (13)	0.0186 (16)	0.0091 (14)	0.0054 (11)	−0.0001 (10)	−0.0026 (11)
C11B	0.0205 (16)	0.0169 (16)	0.0202 (16)	−0.0051 (13)	0.0054 (12)	−0.0008 (13)
C10B	0.0227 (17)	0.0199 (17)	0.0209 (17)	−0.0036 (13)	0.0043 (13)	−0.0103 (13)
C14A	0.0303 (18)	0.0191 (17)	0.0120 (15)	0.0030 (13)	0.0061 (12)	0.0031 (12)

S1—C5A	1.772 (3)	C13B—N5B	1.475 (4)
S1—C14A	1.802 (3)	C13B—H5A1	0.9800
N1A—C7A	1.282 (4)	C13B—H5A2	0.9800
N1A—C8A	1.391 (4)	C13B—H5A3	0.9800
C6B—N4B	1.329 (4)	C13A—H1'1	0.9800
C6B—N2B	1.377 (4)	C13A—H1'2	0.9800
C6B—C5B	1.409 (4)	C13A—H1'3	0.9800
C10A—O2A	1.225 (3)	N4B—C4B	1.341 (4)
C10A—N4A	1.373 (4)	C5B—C8B	1.455 (4)
C10A—N3A	1.388 (4)	N2A—C11A	1.339 (4)
O1B—C1B	1.203 (4)	N2A—H101	0.85 (4)
C9A—O1A	1.232 (3)	N2A—H102	0.96 (4)
C9A—N4A	1.419 (4)	N5B—C4B	1.369 (4)
C9A—C8A	1.430 (4)	N5B—C1B	1.393 (4)
O2B—C2B	1.220 (3)	C11A—C8A	1.399 (4)
C2B—N6B	1.387 (4)	C3A—C2A	1.391 (4)
C2B—C3B	1.473 (4)	C3A—C4A	1.400 (4)
N3A—C11A	1.379 (4)	C3A—H3	0.9500
N3A—C12A	1.467 (4)	C7A—C6A	1.464 (4)
O3A—C7B	1.213 (3)	C7A—H7	0.9500
N2B—C7B	1.384 (4)	C5A—C4A	1.394 (4)
N2B—C12B	1.472 (4)	C5A—C6A	1.421 (4)
O4A—C8B	1.231 (3)	C2A—C1A	1.388 (4)
N1B—C8B	1.382 (4)	C2A—H4	0.9500
N1B—C7B	1.409 (4)	C6A—C1A	1.397 (4)
N1B—C11B	1.469 (4)	C4A—H2	0.9500
C12A—H2'1	0.9800	C1A—H5	0.9500
C12A—H2'2	0.9800	C3B—C4B	1.420 (4)
C12A—H2'3	0.9800	C11B—H9A1	0.9800
N4A—C13A	1.468 (3)	C11B—H9A2	0.9800
N6B—C1B	1.407 (4)	C11B—H9A3	0.9800
N6B—C10B	1.475 (4)	C10B—H6A1	0.9800
N3B—C3B	1.324 (4)	C10B—H6A2	0.9800
N3B—C5B	1.335 (4)	C10B—H6A3	0.9800
C12B—H8A1	0.9800	C14A—H20A	0.9800
C12B—H8A2	0.9800	C14A—H20B	0.9800
C12B—H8A3	0.9800	C14A—H20C	0.9800
C5A—S1—C14A	103.51 (14)	C4B—N5B—C13B	121.4 (2)
C7A—N1A—C8A	124.5 (3)	C1B—N5B—C13B	116.0 (2)
N4B—C6B—N2B	117.7 (2)	N2A—C11A—N3A	117.6 (3)
N4B—C6B—C5B	123.0 (3)	N2A—C11A—C8A	122.2 (3)
N2B—C6B—C5B	119.2 (3)	N3A—C11A—C8A	120.2 (3)
O2A—C10A—N4A	122.0 (3)	C2A—C3A—C4A	120.3 (3)
O2A—C10A—N3A	121.4 (3)	C2A—C3A—H3	119.9
N4A—C10A—N3A	116.6 (2)	C4A—C3A—H3	119.9
O1A—C9A—N4A	118.1 (3)	N1A—C7A—C6A	120.4 (3)
O1A—C9A—C8A	126.1 (3)	N1A—C7A—H7	119.8
N4A—C9A—C8A	115.8 (2)	C6A—C7A—H7	119.8
O2B—C2B—N6B	122.1 (3)	C4A—C5A—C6A	119.5 (3)
O2B—C2B—C3B	123.5 (3)	C4A—C5A—S1	123.0 (2)
N6B—C2B—C3B	114.4 (2)	C6A—C5A—S1	117.6 (2)
C11A—N3A—C10A	122.6 (2)	O4A—C8B—N1B	121.1 (3)
C11A—N3A—C12A	120.4 (2)	O4A—C8B—C5B	123.4 (3)
C10A—N3A—C12A	117.0 (2)	N1B—C8B—C5B	115.5 (2)
C6B—N2B—C7B	122.7 (2)	O3A—C7B—N2B	122.5 (3)
C6B—N2B—C12B	120.2 (2)	O3A—C7B—N1B	120.5 (3)
C7B—N2B—C12B	117.1 (2)	N2B—C7B—N1B	117.0 (2)
C8B—N1B—C7B	124.7 (3)	O1B—C1B—N5B	122.0 (3)
C8B—N1B—C11B	119.1 (2)	O1B—C1B—N6B	121.5 (3)
C7B—N1B—C11B	115.9 (2)	N5B—C1B—N6B	116.5 (3)
N3A—C12A—H2'1	109.5	N1A—C8A—C11A	114.9 (2)
N3A—C12A—H2'2	109.5	N1A—C8A—C9A	125.2 (2)
H2'1—C12A—H2'2	109.5	C11A—C8A—C9A	120.0 (3)
N3A—C12A—H2'3	109.5	C1A—C2A—C3A	119.5 (3)
H2'1—C12A—H2'3	109.5	C1A—C2A—H4	120.3
H2'2—C12A—H2'3	109.5	C3A—C2A—H4	120.3
C10A—N4A—C9A	124.9 (2)	C1A—C6A—C5A	118.8 (3)
C10A—N4A—C13A	115.8 (2)	C1A—C6A—C7A	119.9 (3)
C9A—N4A—C13A	119.3 (2)	C5A—C6A—C7A	121.3 (2)
C2B—N6B—C1B	126.0 (2)	C5A—C4A—C3A	120.4 (3)
C2B—N6B—C10B	118.4 (2)	C5A—C4A—H2	119.8
C1B—N6B—C10B	115.6 (3)	C3A—C4A—H2	119.8
C3B—N3B—C5B	117.2 (2)	C2A—C1A—C6A	121.5 (3)
N2B—C12B—H8A1	109.5	C2A—C1A—H5	119.3
N2B—C12B—H8A2	109.5	C6A—C1A—H5	119.3
H8A1—C12B—H8A2	109.5	N3B—C3B—C4B	121.5 (3)
N2B—C12B—H8A3	109.5	N3B—C3B—C2B	118.4 (2)
H8A1—C12B—H8A3	109.5	C4B—C3B—C2B	120.1 (3)
H8A2—C12B—H8A3	109.5	N4B—C4B—N5B	118.1 (2)
N5B—C13B—H5A1	109.5	N4B—C4B—C3B	121.8 (3)
N5B—C13B—H5A2	109.5	N5B—C4B—C3B	120.1 (3)
H5A1—C13B—H5A2	109.5	N1B—C11B—H9A1	109.5
N5B—C13B—H5A3	109.5	N1B—C11B—H9A2	109.5
H5A1—C13B—H5A3	109.5	H9A1—C11B—H9A2	109.5
H5A2—C13B—H5A3	109.5	N1B—C11B—H9A3	109.5
N4A—C13A—H1'1	109.5	H9A1—C11B—H9A3	109.5
N4A—C13A—H1'2	109.5	H9A2—C11B—H9A3	109.5
H1'1—C13A—H1'2	109.5	N6B—C10B—H6A1	109.5
N4A—C13A—H1'3	109.5	N6B—C10B—H6A2	109.5
H1'1—C13A—H1'3	109.5	H6A1—C10B—H6A2	109.5
H1'2—C13A—H1'3	109.5	N6B—C10B—H6A3	109.5
C6B—N4B—C4B	115.6 (2)	H6A1—C10B—H6A3	109.5
N3B—C5B—C6B	120.9 (3)	H6A2—C10B—H6A3	109.5
N3B—C5B—C8B	118.4 (2)	S1—C14A—H20A	109.5
C6B—C5B—C8B	120.8 (3)	S1—C14A—H20B	109.5
C11A—N2A—H101	116 (2)	H20A—C14A—H20B	109.5
C11A—N2A—H102	125 (2)	S1—C14A—H20C	109.5
H101—N2A—H102	118 (3)	H20A—C14A—H20C	109.5
C4B—N5B—C1B	122.6 (2)	H20B—C14A—H20C	109.5
O2A—C10A—N3A—C11A	179.6 (3)	C8B—N1B—C7B—N2B	2.3 (4)
N4A—C10A—N3A—C11A	−1.0 (4)	C11B—N1B—C7B—N2B	175.0 (2)
O2A—C10A—N3A—C12A	0.8 (4)	C4B—N5B—C1B—O1B	178.7 (3)
N4A—C10A—N3A—C12A	−179.7 (3)	C13B—N5B—C1B—O1B	−1.7 (4)
N4B—C6B—N2B—C7B	178.6 (3)	C4B—N5B—C1B—N6B	−1.3 (4)
C5B—C6B—N2B—C7B	−2.0 (4)	C13B—N5B—C1B—N6B	178.3 (3)
N4B—C6B—N2B—C12B	−0.9 (4)	C2B—N6B—C1B—O1B	−174.9 (3)
C5B—C6B—N2B—C12B	178.5 (3)	C10B—N6B—C1B—O1B	3.4 (4)
O2A—C10A—N4A—C9A	178.1 (3)	C2B—N6B—C1B—N5B	5.1 (4)
N3A—C10A—N4A—C9A	−1.3 (4)	C10B—N6B—C1B—N5B	−176.6 (2)
O2A—C10A—N4A—C13A	−2.4 (4)	C7A—N1A—C8A—C11A	−179.1 (3)
N3A—C10A—N4A—C13A	178.1 (2)	C7A—N1A—C8A—C9A	0.5 (5)
O1A—C9A—N4A—C10A	−178.9 (3)	N2A—C11A—C8A—N1A	−2.3 (4)
C8A—C9A—N4A—C10A	1.7 (4)	N3A—C11A—C8A—N1A	177.4 (2)
O1A—C9A—N4A—C13A	1.6 (4)	N2A—C11A—C8A—C9A	178.1 (3)
C8A—C9A—N4A—C13A	−177.7 (2)	N3A—C11A—C8A—C9A	−2.2 (4)
O2B—C2B—N6B—C1B	174.2 (3)	O1A—C9A—C8A—N1A	1.2 (5)
C3B—C2B—N6B—C1B	−6.4 (4)	N4A—C9A—C8A—N1A	−179.5 (3)
O2B—C2B—N6B—C10B	−4.1 (4)	O1A—C9A—C8A—C11A	−179.2 (3)
C3B—C2B—N6B—C10B	175.4 (2)	N4A—C9A—C8A—C11A	0.1 (4)
N2B—C6B—N4B—C4B	179.0 (2)	C4A—C3A—C2A—C1A	−0.8 (4)
C5B—C6B—N4B—C4B	−0.4 (4)	C4A—C5A—C6A—C1A	−0.8 (4)
C3B—N3B—C5B—C6B	−0.6 (4)	S1—C5A—C6A—C1A	178.6 (2)
C3B—N3B—C5B—C8B	178.9 (3)	C4A—C5A—C6A—C7A	179.9 (3)
N4B—C6B—C5B—N3B	0.5 (4)	S1—C5A—C6A—C7A	−0.8 (4)
N2B—C6B—C5B—N3B	−178.9 (3)	N1A—C7A—C6A—C1A	−1.0 (4)
N4B—C6B—C5B—C8B	−179.0 (3)	N1A—C7A—C6A—C5A	178.3 (3)
N2B—C6B—C5B—C8B	1.6 (4)	C6A—C5A—C4A—C3A	1.2 (4)
C10A—N3A—C11A—N2A	−177.6 (3)	S1—C5A—C4A—C3A	−178.1 (2)
C12A—N3A—C11A—N2A	1.1 (4)	C2A—C3A—C4A—C5A	−0.5 (4)
C10A—N3A—C11A—C8A	2.7 (4)	C3A—C2A—C1A—C6A	1.2 (4)
C12A—N3A—C11A—C8A	−178.6 (3)	C5A—C6A—C1A—C2A	−0.5 (4)
C8A—N1A—C7A—C6A	179.3 (3)	C7A—C6A—C1A—C2A	178.9 (3)
C14A—S1—C5A—C4A	−0.3 (3)	C5B—N3B—C3B—C4B	0.6 (4)
C14A—S1—C5A—C6A	−179.7 (2)	C5B—N3B—C3B—C2B	−178.9 (2)
C7B—N1B—C8B—O4A	177.1 (3)	O2B—C2B—C3B—N3B	3.0 (4)
C11B—N1B—C8B—O4A	4.6 (4)	N6B—C2B—C3B—N3B	−176.5 (2)
C7B—N1B—C8B—C5B	−2.6 (4)	O2B—C2B—C3B—C4B	−176.5 (3)
C11B—N1B—C8B—C5B	−175.1 (3)	N6B—C2B—C3B—C4B	4.1 (4)
N3B—C5B—C8B—O4A	1.4 (4)	C6B—N4B—C4B—N5B	−179.7 (2)
C6B—C5B—C8B—O4A	−179.1 (3)	C6B—N4B—C4B—C3B	0.4 (4)
N3B—C5B—C8B—N1B	−178.9 (2)	C1B—N5B—C4B—N4B	179.6 (3)
C6B—C5B—C8B—N1B	0.6 (4)	C13B—N5B—C4B—N4B	0.0 (4)
C6B—N2B—C7B—O3A	−179.0 (3)	C1B—N5B—C4B—C3B	−0.5 (4)
C12B—N2B—C7B—O3A	0.4 (4)	C13B—N5B—C4B—C3B	179.9 (3)
C6B—N2B—C7B—N1B	0.2 (4)	N3B—C3B—C4B—N4B	−0.5 (4)
C12B—N2B—C7B—N1B	179.6 (2)	C2B—C3B—C4B—N4B	178.9 (2)
C8B—N1B—C7B—O3A	−178.5 (3)	N3B—C3B—C4B—N5B	179.6 (3)
C11B—N1B—C7B—O3A	−5.8 (4)	C2B—C3B—C4B—N5B	−0.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H101···N1A	0.85 (4)	2.32 (3)	2.701 (4)	107 (2)
N2A—H101···O2Bi	0.85 (4)	2.37 (3)	3.078 (3)	141 (3)
N2A—H102···O4Ai	0.96 (4)	2.29 (4)	3.238 (3)	169 (3)
C12A—H2′1···O2A	0.98	2.25	2.706 (4)	107
C4A—H2···O2Aii	0.95	2.58	3.159 (4)	119
C3A—H3···O2Aii	0.95	2.49	3.114 (4)	123
C12A—H2′3···O4Ai	0.98	2.36	3.014 (4)	123
C1A—H5···O2Bi	0.95	2.45	3.339 (4)	155
C12B—H8A2···O3A	0.98	2.33	2.720 (4)	103
C7A—H7···S1	0.95	2.59	3.017 (3)	108
C7A—H7···O1A	0.95	2.18	2.849 (3)	127
C13B—H5A1···O2Bi	0.98	2.50	3.315 (4)	140
C13B—H5A3···N4B	0.98	2.34	2.770 (4)	106
C13A—H1′2···O1A	0.98	2.28	2.726 (4)	107
C11B—H9A1···O4A	0.98	2.37	2.744 (4)	102
C10B—H6A3···O2B	0.98	2.31	2.751 (4)	107
C10B—H6A1···O1Aiii	0.98	2.58	3.542 (4)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H101⋯N1A	0.85 (4)	2.32 (3)	2.701 (4)	107 (2)
N2A—H101⋯O2B i	0.85 (4)	2.37 (3)	3.078 (3)	141 (3)
N2A—H102⋯O4A i	0.96 (4)	2.29 (4)	3.238 (3)	169 (3)
C4A—H2⋯O2A ii	0.95	2.58	3.159 (4)	119
C3A—H3⋯O2A ii	0.95	2.49	3.114 (4)	123
C12A—H2′3⋯O4A i	0.98	2.36	3.014 (4)	123
C1A—H5⋯O2B i	0.95	2.45	3.339 (4)	155
C7A—H7⋯S1	0.95	2.59	3.017 (3)	108
C7A—H7⋯O1A	0.95	2.18	2.849 (3)	127
C13B—H5A1⋯O2B i	0.98	2.50	3.315 (4)	140
C10B—H6A1⋯O1A iii	0.98	2.58	3.542 (4)	169

Symmetry codes: (i) ; (ii) ; (iii) .