Amino-[(1H-benzimidazol-2-yl)amino]-methaniminium 4-methyl-benzene-sulfonate.

The asymmetric unit of the title salt, C8H10N5 (+)·C7H7O3S(-), consists of two amino-[(1H-benzimidazol-2-yl)amino]-meth-an-im-inium cations and two 4-methyl-benzene-sulfonate anions. The cations are each stabilized by intra-molecular N-H⋯N hydrogen bonds between the free amino groups and the imine N atoms of the benzimidazole units, forming S(6) ring motifs. In the crystal, cations and anions are linked by N-H⋯O and C-H⋯O hydrogen bonds, forming a three-dimensional supra-molecular framework. Two strong π-π stacking inter-actions [centroid-centroid distances = 3.4112 (14) and 3.4104 (14) Å] also occur between the centroids of the imidazole rings of like cations.

Related literature

For the synthesis of guanidine-containing compounds, see: Wu et al. (2002 ▶); Hopkins et al. (2002 ▶); Kilburn et al. (2002 ▶); Manimala & Anslyn (2002 ▶). For pharmaceutical and chemical applications of guanidines, see: Han et al. (2008 ▶); Hannon & Anslyn (1993 ▶); Ekelund et al. (2001 ▶); Kovacevic & Maksic (2001 ▶); Costa et al. (1998 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶) and for standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H10N5 +·C7H7O3S−

M = 347.41

Monoclinic,

a = 12.3821 (4) Å

b = 17.8077 (7) Å

c = 14.5112 (5) Å

β = 90.013 (2)°

V = 3199.7 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 100 K

0.35 × 0.10 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer

20618 measured reflections

5679 independent reflections

4108 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.109

S = 1.05

5679 reflections

469 parameters

15 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813024975/sj5349sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813024975/sj5349Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813024975/sj5349Isup3.cml

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

C8H10N5+·C7H7O3S−	F(000) = 1456
Mr = 347.41	Dx = 1.442 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9624 reflections
a = 12.3821 (4) Å	θ = 2.5–25.1°
b = 17.8077 (7) Å	µ = 0.23 mm−1
c = 14.5112 (5) Å	T = 100 K
β = 90.013 (2)°	Plate, colourless
V = 3199.7 (2) Å3	0.35 × 0.10 × 0.04 mm
Z = 8

Bruker APEXII CCD diffractometer	4108 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.044
Graphite monochromator	θmax = 25.1°, θmin = 2.5°
φ and ω scans	h = −14→14
20618 measured reflections	k = −17→21
5679 independent reflections	l = −17→17

Refinement on F2	15 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.044	W = 1/[Σ2(FO2) + (0.0495P)2 + 1.3622P] where P = (FO2 + 2FC2)/3
wR(F2) = 0.109	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.33 e Å−3
5679 reflections	Δρmin = −0.38 e Å−3
469 parameters

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
N1	−0.06286 (16)	0.53699 (11)	0.14245 (14)	0.0175 (6)
N2	0.09357 (15)	0.48502 (11)	0.09774 (13)	0.0169 (6)
N3	−0.03173 (16)	0.40955 (11)	0.18217 (14)	0.0180 (6)
N4	0.12756 (17)	0.34452 (13)	0.15854 (15)	0.0213 (7)
N5	−0.01669 (17)	0.28656 (13)	0.22877 (15)	0.0228 (7)
C8	−0.00584 (19)	0.59345 (14)	0.09792 (15)	0.0175 (8)
C9	−0.0290 (2)	0.66825 (15)	0.08044 (17)	0.0225 (8)
C10	0.0487 (2)	0.70888 (15)	0.03340 (18)	0.0267 (9)
C11	0.1448 (2)	0.67604 (14)	0.00378 (18)	0.0239 (8)
C12	0.1676 (2)	0.60121 (14)	0.02124 (16)	0.0210 (8)
C13	0.09108 (19)	0.56002 (14)	0.06984 (16)	0.0169 (7)
C14	0.00195 (18)	0.47560 (13)	0.14059 (16)	0.0158 (7)
C15	0.02761 (19)	0.34569 (14)	0.18891 (16)	0.0181 (8)
N6	0.56311 (16)	0.46290 (12)	1.14251 (14)	0.0176 (7)
N7	0.40627 (15)	0.51515 (11)	1.09786 (13)	0.0165 (6)
N8	0.53226 (16)	0.59052 (11)	1.18216 (14)	0.0174 (6)
N9	0.37236 (17)	0.65557 (12)	1.15834 (15)	0.0206 (7)
N10	0.51667 (17)	0.71349 (13)	1.22845 (15)	0.0239 (7)
C23	0.50569 (19)	0.40666 (14)	1.09794 (16)	0.0174 (7)
C24	0.5292 (2)	0.33155 (14)	1.08030 (18)	0.0230 (8)
C25	0.4513 (2)	0.29117 (15)	1.03352 (18)	0.0256 (8)
C26	0.3551 (2)	0.32380 (14)	1.00391 (18)	0.0240 (8)
C27	0.33247 (19)	0.39879 (14)	1.02117 (16)	0.0208 (8)
C28	0.40902 (19)	0.43994 (14)	1.06964 (16)	0.0170 (7)
C29	0.49835 (18)	0.52464 (14)	1.14061 (15)	0.0162 (8)
C30	0.47239 (19)	0.65446 (14)	1.18866 (16)	0.0168 (8)
S1	0.21220 (5)	0.14511 (3)	0.19245 (4)	0.0171 (2)
O1	0.25453 (12)	0.08701 (10)	0.25384 (11)	0.0209 (5)
O2	0.09531 (12)	0.14896 (9)	0.19288 (11)	0.0208 (5)
O3	0.26233 (12)	0.21792 (9)	0.21165 (11)	0.0199 (5)
C1	0.25080 (18)	0.12068 (13)	0.07911 (17)	0.0182 (8)
C2	0.1867 (2)	0.14390 (16)	0.00683 (19)	0.0307 (9)
C3	0.2188 (2)	0.13075 (18)	−0.08296 (19)	0.0363 (10)
C4	0.3145 (2)	0.09439 (17)	−0.10240 (19)	0.0312 (9)
C5	0.3776 (2)	0.07199 (19)	−0.0290 (2)	0.0385 (10)
C6	0.3467 (2)	0.08403 (17)	0.06154 (19)	0.0321 (9)
C7	0.3494 (2)	0.0806 (2)	−0.2003 (2)	0.0464 (13)
S2	0.71207 (5)	0.14502 (3)	0.80768 (4)	0.0170 (2)
O4	0.59550 (13)	0.14897 (10)	0.80726 (11)	0.0211 (5)
O5	0.76233 (12)	0.21802 (9)	0.78844 (11)	0.0210 (5)
O6	0.75459 (13)	0.08684 (10)	0.74612 (11)	0.0218 (5)
C16	0.8464 (2)	0.08440 (17)	0.93848 (19)	0.0330 (9)
C17	0.8775 (2)	0.07195 (19)	1.0293 (2)	0.0397 (10)
C18	0.8143 (2)	0.09440 (17)	1.10254 (18)	0.0295 (9)
C19	0.7187 (2)	0.13093 (18)	1.08268 (19)	0.0353 (10)
C20	0.6868 (2)	0.14404 (16)	0.99331 (19)	0.0301 (9)
C21	0.75051 (19)	0.12081 (14)	0.92102 (16)	0.0178 (8)
C22	0.8491 (2)	0.0808 (2)	1.2004 (2)	0.0486 (13)
HN1	−0.1196 (16)	0.5434 (14)	0.1755 (16)	0.0210*
HN3	−0.0980 (14)	0.4078 (15)	0.1986 (17)	0.0220*
H4A	0.148 (2)	0.3840 (12)	0.1274 (17)	0.0260*
H4B	0.1687 (18)	0.3051 (12)	0.1641 (18)	0.0260*
H5A	−0.0860 (14)	0.2874 (16)	0.2457 (18)	0.0270*
H5B	0.021 (2)	0.2448 (12)	0.2250 (19)	0.0270*
H9	−0.09500	0.69050	0.09980	0.0270*
H10	0.03620	0.76050	0.02100	0.0320*
H11	0.19580	0.70560	−0.02910	0.0290*
H12	0.23300	0.57890	0.00080	0.0250*
HN6	0.6213 (15)	0.4571 (15)	1.1766 (16)	0.0210*
HN8	0.5993 (14)	0.5904 (15)	1.2000 (16)	0.0210*
H9A	0.353 (2)	0.6174 (12)	1.1260 (16)	0.0250*
H9B	0.3349 (19)	0.6944 (12)	1.1706 (18)	0.0250*
H10A	0.478 (2)	0.7546 (12)	1.2263 (19)	0.0290*
H10B	0.5849 (14)	0.7141 (16)	1.2466 (18)	0.0290*
H24	0.59530	0.30930	1.09940	0.0280*
H25	0.46380	0.23950	1.02110	0.0310*
H26	0.30410	0.29410	0.97130	0.0290*
H27	0.26710	0.42120	1.00060	0.0250*
H2	0.12040	0.16900	0.01870	0.0370*
H3	0.17410	0.14710	−0.13220	0.0440*
H5	0.44430	0.04750	−0.04100	0.0460*
H6	0.39100	0.06730	0.11090	0.0390*
H7A	0.33560	0.12570	−0.23730	0.0690*
H7B	0.30860	0.03830	−0.22580	0.0690*
H7C	0.42680	0.06900	−0.20160	0.0690*
H16	0.89080	0.06800	0.88910	0.0400*
H17	0.94410	0.04730	1.04120	0.0480*
H19	0.67400	0.14740	1.13190	0.0420*
H20	0.62060	0.16920	0.98150	0.0360*
H22A	0.80090	0.04390	1.22900	0.0730*
H22B	0.84580	0.12800	1.23500	0.0730*
H22C	0.92330	0.06170	1.20100	0.0730*

	U11	U22	U33	U12	U13	U23
N1	0.0175 (11)	0.0148 (11)	0.0202 (11)	0.0030 (9)	0.0011 (8)	−0.0053 (9)
N2	0.0175 (11)	0.0146 (11)	0.0187 (10)	0.0009 (9)	−0.0013 (8)	−0.0022 (9)
N3	0.0129 (10)	0.0180 (12)	0.0232 (11)	0.0025 (9)	0.0019 (8)	0.0001 (9)
N4	0.0207 (12)	0.0157 (13)	0.0275 (12)	0.0043 (9)	0.0027 (9)	0.0042 (10)
N5	0.0198 (11)	0.0176 (13)	0.0311 (12)	0.0049 (10)	0.0052 (9)	0.0061 (10)
C8	0.0206 (13)	0.0171 (14)	0.0149 (12)	0.0004 (10)	−0.0044 (9)	−0.0027 (10)
C9	0.0251 (14)	0.0175 (14)	0.0249 (13)	0.0049 (11)	−0.0062 (11)	−0.0048 (11)
C10	0.0340 (16)	0.0160 (15)	0.0300 (14)	0.0006 (12)	−0.0085 (12)	0.0008 (12)
C11	0.0266 (14)	0.0202 (14)	0.0250 (13)	−0.0053 (11)	−0.0048 (11)	0.0034 (12)
C12	0.0209 (13)	0.0218 (15)	0.0204 (13)	−0.0014 (11)	−0.0038 (10)	−0.0014 (11)
C13	0.0204 (13)	0.0124 (13)	0.0178 (12)	0.0007 (10)	−0.0059 (10)	−0.0037 (10)
C14	0.0170 (12)	0.0141 (13)	0.0162 (12)	0.0004 (10)	−0.0025 (9)	−0.0028 (10)
C15	0.0180 (13)	0.0197 (15)	0.0167 (12)	0.0020 (11)	−0.0008 (10)	−0.0011 (10)
N6	0.0163 (11)	0.0157 (12)	0.0208 (11)	0.0034 (9)	−0.0005 (8)	0.0031 (9)
N7	0.0190 (11)	0.0135 (11)	0.0171 (10)	0.0001 (9)	0.0012 (8)	0.0004 (9)
N8	0.0142 (10)	0.0154 (12)	0.0227 (11)	0.0021 (9)	−0.0021 (8)	0.0005 (9)
N9	0.0200 (12)	0.0127 (12)	0.0290 (12)	0.0035 (9)	−0.0014 (9)	−0.0056 (10)
N10	0.0198 (12)	0.0177 (13)	0.0342 (13)	0.0039 (10)	−0.0042 (10)	−0.0051 (10)
C23	0.0201 (13)	0.0146 (13)	0.0174 (12)	−0.0003 (10)	0.0049 (10)	0.0027 (10)
C24	0.0250 (14)	0.0169 (14)	0.0272 (14)	0.0042 (11)	0.0062 (11)	0.0025 (11)
C25	0.0318 (15)	0.0137 (14)	0.0312 (15)	−0.0006 (12)	0.0112 (12)	−0.0005 (12)
C26	0.0268 (14)	0.0190 (14)	0.0262 (14)	−0.0059 (12)	0.0044 (11)	−0.0033 (12)
C27	0.0185 (13)	0.0205 (15)	0.0234 (13)	−0.0014 (11)	0.0050 (10)	0.0014 (11)
C28	0.0203 (13)	0.0150 (13)	0.0156 (12)	0.0009 (10)	0.0052 (10)	0.0030 (10)
C29	0.0178 (13)	0.0161 (14)	0.0148 (12)	0.0009 (10)	0.0021 (9)	0.0030 (10)
C30	0.0184 (13)	0.0166 (14)	0.0153 (12)	−0.0007 (10)	0.0007 (10)	0.0001 (10)
S1	0.0165 (3)	0.0142 (3)	0.0205 (3)	0.0006 (2)	0.0007 (2)	0.0022 (3)
O1	0.0190 (9)	0.0171 (10)	0.0267 (9)	0.0007 (7)	−0.0013 (7)	0.0067 (8)
O2	0.0166 (9)	0.0212 (10)	0.0245 (9)	0.0000 (7)	0.0024 (7)	0.0013 (8)
O3	0.0222 (9)	0.0130 (9)	0.0245 (9)	−0.0008 (7)	−0.0026 (7)	0.0001 (7)
C1	0.0182 (13)	0.0117 (13)	0.0246 (13)	−0.0023 (10)	0.0032 (10)	0.0000 (11)
C2	0.0279 (15)	0.0370 (17)	0.0272 (14)	0.0119 (13)	0.0009 (12)	−0.0022 (13)
C3	0.0344 (17)	0.049 (2)	0.0254 (15)	0.0067 (14)	−0.0032 (12)	−0.0034 (14)
C4	0.0267 (15)	0.0379 (18)	0.0291 (15)	−0.0119 (13)	0.0026 (12)	−0.0130 (13)
C5	0.0242 (15)	0.051 (2)	0.0404 (18)	0.0084 (14)	0.0052 (13)	−0.0144 (15)
C6	0.0251 (15)	0.0411 (19)	0.0302 (15)	0.0109 (13)	−0.0043 (12)	−0.0029 (14)
C7	0.0329 (17)	0.073 (3)	0.0332 (17)	−0.0122 (16)	0.0085 (13)	−0.0214 (17)
S2	0.0163 (3)	0.0140 (3)	0.0206 (3)	0.0006 (2)	−0.0008 (2)	−0.0022 (3)
O4	0.0170 (9)	0.0209 (10)	0.0253 (9)	0.0016 (7)	−0.0014 (7)	−0.0022 (8)
O5	0.0213 (9)	0.0137 (10)	0.0279 (9)	−0.0003 (7)	0.0010 (7)	−0.0009 (8)
O6	0.0196 (9)	0.0186 (10)	0.0271 (9)	0.0019 (7)	0.0010 (7)	−0.0054 (8)
C16	0.0260 (15)	0.0418 (19)	0.0311 (15)	0.0109 (13)	0.0044 (12)	0.0083 (14)
C17	0.0252 (16)	0.053 (2)	0.0410 (18)	0.0095 (14)	−0.0048 (13)	0.0168 (16)
C18	0.0275 (15)	0.0349 (18)	0.0262 (14)	−0.0088 (13)	−0.0032 (11)	0.0110 (13)
C19	0.0334 (16)	0.048 (2)	0.0245 (15)	0.0070 (14)	0.0019 (12)	0.0014 (14)
C20	0.0271 (15)	0.0367 (17)	0.0266 (14)	0.0116 (13)	−0.0002 (11)	0.0016 (13)
C21	0.0194 (13)	0.0114 (13)	0.0226 (13)	−0.0029 (10)	−0.0044 (10)	0.0016 (10)
C22	0.0365 (18)	0.075 (3)	0.0342 (17)	−0.0139 (17)	−0.0102 (14)	0.0238 (18)

S1—O2	1.4490 (16)	C9—H9	0.9500
S1—O3	1.4642 (17)	C10—H10	0.9500
S1—O1	1.4624 (18)	C11—H11	0.9500
S1—C1	1.767 (3)	C12—H12	0.9500
S2—C21	1.766 (2)	C23—C24	1.393 (4)
S2—O6	1.4659 (18)	C23—C28	1.397 (3)
S2—O5	1.4681 (17)	C24—C25	1.381 (4)
S2—O4	1.4451 (17)	C25—C26	1.393 (4)
N1—C14	1.356 (3)	C26—C27	1.387 (4)
N1—C8	1.388 (3)	C27—C28	1.389 (3)
N2—C14	1.305 (3)	C24—H24	0.9500
N2—C13	1.396 (3)	C25—H25	0.9500
N3—C15	1.357 (3)	C26—H26	0.9500
N3—C14	1.386 (3)	C27—H27	0.9500
N4—C15	1.314 (3)	C1—C6	1.379 (3)
N5—C15	1.321 (3)	C1—C2	1.379 (4)
N1—HN1	0.86 (2)	C2—C3	1.382 (4)
N3—HN3	0.855 (18)	C3—C4	1.380 (4)
N4—H4A	0.87 (2)	C4—C7	1.505 (4)
N4—H4B	0.87 (2)	C4—C5	1.380 (4)
N5—H5A	0.893 (18)	C5—C6	1.385 (4)
N5—H5B	0.88 (2)	C2—H2	0.9500
N6—C29	1.361 (3)	C3—H3	0.9500
N6—C23	1.388 (3)	C5—H5	0.9500
N7—C28	1.401 (3)	C6—H6	0.9500
N7—C29	1.309 (3)	C7—H7B	0.9800
N8—C29	1.384 (3)	C7—H7C	0.9800
N8—C30	1.362 (3)	C7—H7A	0.9800
N9—C30	1.315 (3)	C16—C17	1.391 (4)
N10—C30	1.319 (3)	C16—C21	1.376 (4)
N6—HN6	0.88 (2)	C17—C18	1.379 (4)
N8—HN8	0.870 (18)	C18—C19	1.381 (4)
N9—H9B	0.85 (2)	C18—C22	1.504 (4)
N9—H9A	0.86 (2)	C19—C20	1.376 (4)
N10—H10B	0.885 (19)	C20—C21	1.376 (4)
N10—H10A	0.88 (2)	C16—H16	0.9500
C8—C9	1.386 (4)	C17—H17	0.9500
C8—C13	1.400 (3)	C19—H19	0.9500
C9—C10	1.384 (4)	C20—H20	0.9500
C10—C11	1.394 (4)	C22—H22A	0.9800
C11—C12	1.386 (4)	C22—H22B	0.9800
C12—C13	1.391 (3)	C22—H22C	0.9800
O2—S1—C1	106.62 (10)	C25—C26—C27	121.2 (2)
O3—S1—C1	106.28 (10)	C26—C27—C28	117.5 (2)
O1—S1—O3	111.02 (10)	N7—C28—C23	109.9 (2)
O1—S1—C1	107.21 (10)	N7—C28—C27	129.5 (2)
O1—S1—O2	112.88 (9)	C23—C28—C27	120.6 (2)
O2—S1—O3	112.38 (9)	N7—C29—N8	125.5 (2)
O6—S2—C21	107.36 (11)	N6—C29—N7	114.7 (2)
O4—S2—O5	112.31 (10)	N6—C29—N8	119.8 (2)
O5—S2—C21	106.21 (11)	N8—C30—N10	118.1 (2)
O5—S2—O6	110.96 (10)	N8—C30—N9	120.2 (2)
O4—S2—O6	113.00 (10)	N9—C30—N10	121.8 (2)
O4—S2—C21	106.55 (11)	C25—C24—H24	122.00
C8—N1—C14	105.87 (19)	C23—C24—H24	122.00
C13—N2—C14	104.01 (19)	C24—C25—H25	119.00
C14—N3—C15	125.4 (2)	C26—C25—H25	119.00
C8—N1—HN1	125.5 (17)	C25—C26—H26	119.00
C14—N1—HN1	127.1 (16)	C27—C26—H26	119.00
C14—N3—HN3	116.2 (18)	C28—C27—H27	121.00
C15—N3—HN3	118.0 (18)	C26—C27—H27	121.00
C15—N4—H4A	115.7 (16)	S1—C1—C6	121.45 (19)
C15—N4—H4B	122.2 (15)	S1—C1—C2	118.58 (18)
H4A—N4—H4B	122 (2)	C2—C1—C6	119.8 (2)
C15—N5—H5A	120.4 (18)	C1—C2—C3	120.1 (2)
H5A—N5—H5B	123 (2)	C2—C3—C4	121.3 (3)
C15—N5—H5B	115.2 (16)	C5—C4—C7	121.3 (2)
C23—N6—C29	105.77 (19)	C3—C4—C5	117.7 (3)
C28—N7—C29	103.93 (19)	C3—C4—C7	121.1 (2)
C29—N8—C30	125.0 (2)	C4—C5—C6	122.1 (2)
C29—N6—HN6	126.1 (17)	C1—C6—C5	119.1 (2)
C23—N6—HN6	126.6 (18)	C1—C2—H2	120.00
C29—N8—HN8	114.7 (17)	C3—C2—H2	120.00
C30—N8—HN8	120.1 (18)	C4—C3—H3	119.00
C30—N9—H9B	117.1 (16)	C2—C3—H3	119.00
C30—N9—H9A	115.7 (16)	C4—C5—H5	119.00
H9A—N9—H9B	127 (2)	C6—C5—H5	119.00
C30—N10—H10B	122.5 (18)	C1—C6—H6	120.00
H10A—N10—H10B	122 (2)	C5—C6—H6	120.00
C30—N10—H10A	115.1 (16)	H7B—C7—H7C	110.00
C9—C8—C13	122.2 (2)	C4—C7—H7A	109.00
N1—C8—C13	105.3 (2)	C4—C7—H7B	110.00
N1—C8—C9	132.5 (2)	C4—C7—H7C	109.00
C8—C9—C10	116.7 (2)	H7A—C7—H7B	109.00
C9—C10—C11	121.8 (2)	H7A—C7—H7C	109.00
C10—C11—C12	121.4 (2)	C17—C16—C21	119.2 (2)
C11—C12—C13	117.5 (2)	C16—C17—C18	121.8 (2)
N2—C13—C8	110.0 (2)	C17—C18—C19	117.5 (2)
C8—C13—C12	120.5 (2)	C17—C18—C22	121.2 (2)
N2—C13—C12	129.6 (2)	C19—C18—C22	121.2 (2)
N1—C14—N3	119.8 (2)	C18—C19—C20	121.5 (2)
N1—C14—N2	114.9 (2)	C19—C20—C21	120.2 (2)
N2—C14—N3	125.3 (2)	S2—C21—C16	121.26 (19)
N4—C15—N5	121.7 (2)	S2—C21—C20	118.83 (19)
N3—C15—N5	118.3 (2)	C16—C21—C20	119.7 (2)
N3—C15—N4	119.9 (2)	C17—C16—H16	120.00
C10—C9—H9	122.00	C21—C16—H16	120.00
C8—C9—H9	122.00	C16—C17—H17	119.00
C11—C10—H10	119.00	C18—C17—H17	119.00
C9—C10—H10	119.00	C18—C19—H19	119.00
C10—C11—H11	119.00	C20—C19—H19	119.00
C12—C11—H11	119.00	C19—C20—H20	120.00
C13—C12—H12	121.00	C21—C20—H20	120.00
C11—C12—H12	121.00	C18—C22—H22A	109.00
N6—C23—C24	132.2 (2)	C18—C22—H22B	109.00
N6—C23—C28	105.6 (2)	C18—C22—H22C	109.00
C24—C23—C28	122.2 (2)	H22A—C22—H22B	109.00
C23—C24—C25	116.4 (2)	H22A—C22—H22C	110.00
C24—C25—C26	122.1 (2)	H22B—C22—H22C	109.00
O1—S1—C1—C2	152.0 (2)	C13—C8—C9—C10	0.1 (4)
O2—S1—C1—C2	30.8 (2)	N1—C8—C9—C10	179.8 (2)
O3—S1—C1—C2	−89.3 (2)	N1—C8—C13—C12	179.1 (2)
O1—S1—C1—C6	−32.8 (2)	C8—C9—C10—C11	1.0 (4)
O2—S1—C1—C6	−153.9 (2)	C9—C10—C11—C12	−0.9 (4)
O3—S1—C1—C6	86.0 (2)	C10—C11—C12—C13	−0.2 (4)
O5—S2—C21—C20	89.1 (2)	C11—C12—C13—C8	1.2 (3)
O6—S2—C21—C20	−152.1 (2)	C11—C12—C13—N2	−179.0 (2)
O6—S2—C21—C16	32.8 (2)	C28—C23—C24—C25	−0.4 (4)
O4—S2—C21—C16	154.2 (2)	N6—C23—C24—C25	179.7 (2)
O5—S2—C21—C16	−85.9 (2)	C24—C23—C28—N7	179.0 (2)
O4—S2—C21—C20	−30.8 (2)	N6—C23—C28—N7	−1.0 (3)
C14—N1—C8—C9	−178.3 (3)	N6—C23—C28—C27	179.2 (2)
C14—N1—C8—C13	1.4 (2)	C24—C23—C28—C27	−0.8 (4)
C8—N1—C14—N3	178.5 (2)	C23—C24—C25—C26	1.1 (4)
C8—N1—C14—N2	−1.8 (3)	C24—C25—C26—C27	−0.8 (4)
C13—N2—C14—N3	−179.0 (2)	C25—C26—C27—C28	−0.4 (4)
C14—N2—C13—C8	−0.3 (3)	C26—C27—C28—C23	1.2 (3)
C13—N2—C14—N1	1.3 (3)	C26—C27—C28—N7	−178.6 (2)
C14—N2—C13—C12	180.0 (2)	S1—C1—C2—C3	175.1 (2)
C14—N3—C15—N5	−178.4 (2)	C2—C1—C6—C5	0.8 (4)
C15—N3—C14—N2	3.6 (4)	C6—C1—C2—C3	−0.3 (4)
C14—N3—C15—N4	3.5 (4)	S1—C1—C6—C5	−174.4 (2)
C15—N3—C14—N1	−176.6 (2)	C1—C2—C3—C4	0.1 (4)
C23—N6—C29—N8	178.4 (2)	C2—C3—C4—C7	−179.7 (3)
C23—N6—C29—N7	−1.5 (3)	C2—C3—C4—C5	−0.4 (4)
C29—N6—C23—C24	−178.6 (3)	C3—C4—C5—C6	1.0 (5)
C29—N6—C23—C28	1.5 (2)	C7—C4—C5—C6	−179.8 (3)
C28—N7—C29—N8	−179.1 (2)	C4—C5—C6—C1	−1.1 (5)
C29—N7—C28—C27	180.0 (3)	C17—C16—C21—C20	−0.3 (4)
C29—N7—C28—C23	0.2 (3)	C17—C16—C21—S2	174.8 (2)
C28—N7—C29—N6	0.8 (3)	C21—C16—C17—C18	0.7 (5)
C30—N8—C29—N6	−176.5 (2)	C16—C17—C18—C19	−0.8 (5)
C29—N8—C30—N9	3.6 (4)	C16—C17—C18—C22	−179.8 (3)
C30—N8—C29—N7	3.4 (4)	C17—C18—C19—C20	0.5 (4)
C29—N8—C30—N10	−178.4 (2)	C22—C18—C19—C20	179.5 (3)
N1—C8—C13—N2	−0.7 (3)	C18—C19—C20—C21	−0.1 (4)
C9—C8—C13—N2	179.0 (2)	C19—C20—C21—C16	0.0 (4)
C9—C8—C13—C12	−1.2 (4)	C19—C20—C21—S2	−175.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O1i	0.86 (2)	2.11 (2)	2.948 (3)	166 (2)
N3—HN3···O6ii	0.86 (2)	1.95 (2)	2.805 (3)	173 (2)
N6—HN6···O6iii	0.88 (2)	2.09 (2)	2.944 (3)	164 (2)
N8—HN8···O1iv	0.87 (2)	1.93 (2)	2.799 (2)	177 (2)
N4—H4A···N2	0.87 (2)	1.97 (2)	2.686 (3)	139 (2)
N4—H4B···O3	0.87 (2)	2.06 (2)	2.909 (3)	166 (2)
N5—H5A···O5ii	0.89 (2)	1.98 (2)	2.871 (3)	176 (3)
N5—H5B···O2	0.88 (2)	1.99 (2)	2.863 (3)	169 (3)
N9—H9A···N7	0.86 (2)	1.98 (2)	2.683 (3)	138 (2)
N9—H9B···O5v	0.85 (2)	2.06 (2)	2.906 (3)	174 (2)
N10—H10A···O4v	0.88 (2)	2.00 (2)	2.863 (3)	167 (3)
N10—H10B···O3iv	0.89 (2)	1.99 (2)	2.872 (3)	179 (3)
C2—H2···O2	0.95	2.57	2.929 (3)	103
C7—H7C···O4vi	0.98	2.53	3.283 (3)	133
C20—H20···O4	0.95	2.57	2.928 (3)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O1i	0.86 (2)	2.11 (2)	2.948 (3)	166 (2)
N3—HN3⋯O6ii	0.86 (2)	1.95 (2)	2.805 (3)	173 (2)
N6—HN6⋯O6iii	0.88 (2)	2.09 (2)	2.944 (3)	164 (2)
N8—HN8⋯O1iv	0.87 (2)	1.93 (2)	2.799 (2)	177 (2)
N4—H4A⋯N2	0.87 (2)	1.97 (2)	2.686 (3)	139 (2)
N4—H4B⋯O3	0.87 (2)	2.06 (2)	2.909 (3)	166 (2)
N5—H5A⋯O5ii	0.89 (2)	1.98 (2)	2.871 (3)	176 (3)
N5—H5B⋯O2	0.88 (2)	1.99 (2)	2.863 (3)	169 (3)
N9—H9A⋯N7	0.86 (2)	1.98 (2)	2.683 (3)	138 (2)
N9—H9B⋯O5v	0.85 (2)	2.06 (2)	2.906 (3)	174 (2)
N10—H10A⋯O4v	0.88 (2)	2.00 (2)	2.863 (3)	167 (3)
N10—H10B⋯O3iv	0.89 (2)	1.99 (2)	2.872 (3)	179 (3)
C7—H7C⋯O4vi	0.98	2.53	3.283 (3)	133

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .