4-Amino-N-(2,3-di-hydro-1,3-thia-zol-2-yl-idene)benzene-sulfonamide-2,4,6-tris-(pyr-idin-2-yl)-1,3,5-triazine (1/1).

The sulfa-thia-zole mol-ecule in the title 1:1 co-crystal, C9H9N3O2S2·C18H12N6, adopts an approximate L-shape [dihedral angle between the five- and six-membered rings = 86.20 (9)°] and features an intra-molecular hypervalent S⋯O inter-action [2.8666 (15) Å]. Overall, the triazine mol-ecule has the shape of a disk as the pendant pyridine rings are relatively close to coplanar with the central ring [dihedral angles = 18.35 (9), 6.12 (9) and 4.67 (9)°]. In the crystal packing, a linear supra-molecular chain aligned along [01-1] is formed as a result of amino-pyridyl N-H⋯N hydrogen bonding with syn-disposed pyridyl mol-ecules of one triazine, and amine-pyridyl N-H⋯N hydrogen bonding with the third pydridyl ring of a second triazine mol-ecule. A three-dimensional architecture arises as the chains are connected by C-H⋯O inter-actions.

Related literature

For previous co-crystallization studies with sulfa­thia­zole, see: Arman et al. (2012 ▶). For the polymorphic 1:1 co-crystals of sulfa­thia­zole and pyridine, see: Drebushchak et al. (2006a ▶,b ▶). For hypervalent S⋯O inter­actions, see: O’Leary & Wallis (2007 ▶).

Experimental

Crystal data

C18H12N6·C9H9N3O2S2

M = 567.65

Triclinic,

a = 8.8109 (13) Å

b = 12.7222 (16) Å

c = 13.1696 (14) Å

α = 66.227 (6)°

β = 73.797 (6)°

γ = 88.068 (9)°

V = 1292.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 98 K

0.49 × 0.45 × 0.05 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.723, T max = 1.000

8512 measured reflections

5885 independent reflections

5490 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.087

S = 0.99

5885 reflections

371 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) general, I. DOI: 10.1107/S1600536814004838/hg5388sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004838/hg5388Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814004838/hg5388Isup3.cml

CCDC reference: 989538

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H12N6·C9H9N3O2S2	Z = 2
Mr = 567.65	F(000) = 588
Triclinic, P1	Dx = 1.459 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8109 (13) Å	Cell parameters from 4931 reflections
b = 12.7222 (16) Å	θ = 3.0–40.2°
c = 13.1696 (14) Å	µ = 0.25 mm−1
α = 66.227 (6)°	T = 98 K
β = 73.797 (6)°	Platelet, gold
γ = 88.068 (9)°	0.49 × 0.45 × 0.05 mm
V = 1292.1 (3) Å3

Rigaku AFC12K/SATURN724 diffractometer	5885 independent reflections
Radiation source: sealed tube	5490 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 2.4°
ω scans	h = −11→7
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −16→12
Tmin = 0.723, Tmax = 1.000	l = −17→17
8512 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.005P)2 + 1.820P] where P = (Fo2 + 2Fc2)/3
5885 reflections	(Δ/σ)max < 0.001
371 parameters	Δρmax = 0.48 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	−0.04089 (5)	0.03018 (4)	0.25889 (5)	0.02706 (12)
S2	0.34188 (5)	0.07956 (3)	0.19769 (3)	0.01620 (10)
O1	0.23839 (15)	0.12511 (11)	0.27391 (10)	0.0209 (3)
O2	0.49844 (15)	0.05721 (11)	0.21024 (11)	0.0223 (3)
N1	0.04768 (19)	−0.14266 (13)	0.21606 (14)	0.0216 (3)
H1N	0.105 (3)	−0.195 (2)	0.196 (2)	0.042 (7)*
N2	0.26444 (17)	−0.04058 (12)	0.21139 (12)	0.0171 (3)
N3	0.3779 (2)	0.37727 (13)	−0.28932 (13)	0.0206 (3)
H2N	0.311 (3)	0.4266 (19)	−0.3067 (18)	0.025*
H3N	0.424 (3)	0.3527 (18)	−0.3439 (19)	0.025*
C1	0.1113 (2)	−0.05352 (14)	0.22511 (14)	0.0174 (3)
C2	−0.1811 (2)	−0.06008 (18)	0.2549 (2)	0.0373 (5)
H2	−0.2907	−0.0488	0.2670	0.045*
C3	−0.1146 (2)	−0.14667 (18)	0.2330 (2)	0.0322 (5)
H3	−0.1729	−0.2058	0.2292	0.039*
C4	0.3594 (2)	0.17515 (14)	0.05455 (14)	0.0166 (3)
C5	0.2596 (2)	0.26325 (15)	0.02888 (15)	0.0197 (3)
H5	0.1867	0.2768	0.0898	0.024*
C6	0.2662 (2)	0.33105 (15)	−0.08495 (15)	0.0203 (3)
H6	0.1987	0.3917	−0.1014	0.024*
C7	0.3712 (2)	0.31199 (14)	−0.17696 (14)	0.0168 (3)
C8	0.4718 (2)	0.22258 (15)	−0.14895 (15)	0.0188 (3)
H8	0.5445	0.2081	−0.2093	0.023*
C9	0.4662 (2)	0.15621 (14)	−0.03585 (15)	0.0182 (3)
H9	0.5355	0.0968	−0.0189	0.022*
N4	0.71021 (17)	0.54364 (12)	0.51665 (12)	0.0169 (3)
N5	0.80820 (17)	0.39937 (12)	0.65988 (12)	0.0178 (3)
N6	0.65974 (18)	0.54222 (12)	0.70455 (12)	0.0180 (3)
N7	0.50169 (17)	0.71447 (12)	0.47243 (12)	0.0178 (3)
N8	0.83810 (18)	0.44100 (13)	0.36693 (13)	0.0202 (3)
N9	0.82618 (18)	0.29923 (13)	0.88291 (13)	0.0209 (3)
C10	0.6468 (2)	0.58500 (14)	0.59665 (14)	0.0169 (3)
C11	0.7905 (2)	0.45104 (14)	0.55329 (14)	0.0171 (3)
C12	0.7410 (2)	0.44915 (14)	0.73159 (14)	0.0173 (3)
C13	0.5545 (2)	0.68775 (14)	0.56574 (14)	0.0164 (3)
C14	0.4165 (2)	0.80561 (15)	0.44615 (15)	0.0195 (3)
H14	0.3777	0.8251	0.3809	0.023*
C15	0.3814 (2)	0.87340 (15)	0.50870 (15)	0.0211 (4)
H15	0.3192	0.9367	0.4873	0.025*
C16	0.4393 (2)	0.84643 (15)	0.60282 (16)	0.0225 (4)
H16	0.4197	0.8921	0.6464	0.027*
C17	0.5265 (2)	0.75155 (15)	0.63252 (15)	0.0200 (3)
H17	0.5665	0.7305	0.6974	0.024*
C18	0.8671 (2)	0.39881 (14)	0.47031 (15)	0.0175 (3)
C19	0.9006 (2)	0.39032 (16)	0.29539 (16)	0.0236 (4)
H19	0.8803	0.4190	0.2222	0.028*
C20	0.9932 (2)	0.29850 (16)	0.32140 (16)	0.0242 (4)
H20	1.0335	0.2646	0.2679	0.029*
C21	1.0255 (2)	0.25734 (16)	0.42662 (16)	0.0236 (4)
H21	1.0901	0.1952	0.4467	0.028*
C22	0.9619 (2)	0.30844 (15)	0.50265 (15)	0.0205 (3)
H22	0.9828	0.2822	0.5755	0.025*
C23	0.7547 (2)	0.39769 (14)	0.85213 (15)	0.0185 (3)
C24	0.8363 (2)	0.25076 (16)	0.99140 (16)	0.0253 (4)
H24	0.8869	0.1813	1.0139	0.030*
C25	0.7773 (2)	0.29598 (17)	1.07283 (16)	0.0262 (4)
H25	0.7867	0.2582	1.1492	0.031*
C26	0.7044 (2)	0.39730 (17)	1.04045 (16)	0.0274 (4)
H26	0.6625	0.4306	1.0942	0.033*
C27	0.6937 (2)	0.44959 (16)	0.92786 (16)	0.0238 (4)
H27	0.6453	0.5198	0.9031	0.029*

	U11	U22	U33	U12	U13	U23
S1	0.0168 (2)	0.0232 (2)	0.0442 (3)	0.00686 (17)	−0.0085 (2)	−0.0174 (2)
S2	0.0161 (2)	0.0180 (2)	0.01595 (19)	0.00379 (15)	−0.00736 (15)	−0.00686 (15)
O1	0.0245 (7)	0.0229 (6)	0.0183 (6)	0.0043 (5)	−0.0080 (5)	−0.0105 (5)
O2	0.0174 (6)	0.0265 (7)	0.0237 (6)	0.0041 (5)	−0.0113 (5)	−0.0078 (5)
N1	0.0203 (8)	0.0193 (7)	0.0298 (8)	0.0049 (6)	−0.0112 (6)	−0.0123 (6)
N2	0.0167 (7)	0.0161 (7)	0.0189 (7)	0.0044 (5)	−0.0068 (6)	−0.0067 (6)
N3	0.0255 (8)	0.0205 (7)	0.0166 (7)	0.0049 (6)	−0.0076 (6)	−0.0076 (6)
C1	0.0180 (8)	0.0169 (8)	0.0175 (8)	0.0059 (6)	−0.0072 (6)	−0.0062 (6)
C2	0.0188 (10)	0.0312 (11)	0.0659 (16)	0.0044 (8)	−0.0167 (10)	−0.0212 (11)
C3	0.0242 (10)	0.0269 (10)	0.0508 (13)	0.0019 (8)	−0.0187 (9)	−0.0162 (9)
C4	0.0176 (8)	0.0171 (8)	0.0147 (7)	0.0005 (6)	−0.0055 (6)	−0.0055 (6)
C5	0.0220 (9)	0.0200 (8)	0.0174 (8)	0.0059 (7)	−0.0049 (7)	−0.0090 (7)
C6	0.0226 (9)	0.0180 (8)	0.0207 (8)	0.0069 (7)	−0.0074 (7)	−0.0078 (7)
C7	0.0183 (8)	0.0160 (8)	0.0175 (8)	−0.0017 (6)	−0.0071 (6)	−0.0066 (6)
C8	0.0177 (8)	0.0212 (8)	0.0184 (8)	0.0035 (6)	−0.0046 (7)	−0.0095 (7)
C9	0.0159 (8)	0.0179 (8)	0.0215 (8)	0.0044 (6)	−0.0065 (7)	−0.0081 (7)
N4	0.0177 (7)	0.0169 (7)	0.0168 (7)	0.0015 (5)	−0.0063 (6)	−0.0068 (5)
N5	0.0177 (7)	0.0179 (7)	0.0187 (7)	0.0018 (5)	−0.0068 (6)	−0.0076 (6)
N6	0.0214 (7)	0.0164 (7)	0.0174 (7)	0.0022 (6)	−0.0080 (6)	−0.0067 (6)
N7	0.0191 (7)	0.0172 (7)	0.0163 (7)	0.0018 (5)	−0.0060 (6)	−0.0054 (6)
N8	0.0216 (8)	0.0211 (7)	0.0193 (7)	0.0038 (6)	−0.0065 (6)	−0.0096 (6)
N9	0.0245 (8)	0.0197 (7)	0.0210 (7)	0.0046 (6)	−0.0115 (6)	−0.0079 (6)
C10	0.0170 (8)	0.0166 (8)	0.0173 (8)	−0.0002 (6)	−0.0062 (6)	−0.0062 (6)
C11	0.0162 (8)	0.0165 (8)	0.0180 (8)	−0.0007 (6)	−0.0046 (6)	−0.0067 (6)
C12	0.0181 (8)	0.0161 (8)	0.0185 (8)	−0.0001 (6)	−0.0073 (7)	−0.0065 (6)
C13	0.0163 (8)	0.0155 (8)	0.0159 (7)	0.0005 (6)	−0.0044 (6)	−0.0048 (6)
C14	0.0192 (8)	0.0198 (8)	0.0179 (8)	0.0018 (6)	−0.0071 (7)	−0.0051 (7)
C15	0.0204 (9)	0.0181 (8)	0.0225 (8)	0.0047 (7)	−0.0059 (7)	−0.0064 (7)
C16	0.0271 (9)	0.0187 (8)	0.0229 (9)	0.0040 (7)	−0.0060 (7)	−0.0108 (7)
C17	0.0236 (9)	0.0192 (8)	0.0185 (8)	0.0017 (7)	−0.0076 (7)	−0.0080 (7)
C18	0.0163 (8)	0.0170 (8)	0.0183 (8)	−0.0009 (6)	−0.0039 (6)	−0.0068 (6)
C19	0.0278 (10)	0.0259 (9)	0.0193 (8)	0.0041 (7)	−0.0075 (7)	−0.0111 (7)
C20	0.0241 (9)	0.0252 (9)	0.0238 (9)	0.0038 (7)	−0.0028 (7)	−0.0133 (7)
C21	0.0192 (9)	0.0227 (9)	0.0281 (9)	0.0063 (7)	−0.0052 (7)	−0.0109 (7)
C22	0.0183 (8)	0.0219 (8)	0.0205 (8)	0.0026 (7)	−0.0057 (7)	−0.0079 (7)
C23	0.0197 (8)	0.0176 (8)	0.0192 (8)	0.0011 (6)	−0.0082 (7)	−0.0067 (7)
C24	0.0308 (10)	0.0219 (9)	0.0252 (9)	0.0067 (7)	−0.0154 (8)	−0.0071 (7)
C25	0.0322 (10)	0.0284 (10)	0.0195 (9)	0.0049 (8)	−0.0141 (8)	−0.0073 (7)
C26	0.0342 (11)	0.0299 (10)	0.0225 (9)	0.0077 (8)	−0.0115 (8)	−0.0134 (8)
C27	0.0290 (10)	0.0229 (9)	0.0224 (9)	0.0080 (7)	−0.0113 (8)	−0.0098 (7)

S1—C2	1.739 (2)	N7—C13	1.347 (2)
S1—C1	1.7559 (17)	N8—C19	1.335 (2)
S2—O2	1.4401 (13)	N8—C18	1.343 (2)
S2—O1	1.4482 (13)	N9—C24	1.337 (2)
S2—N2	1.6167 (15)	N9—C23	1.345 (2)
S2—C4	1.7489 (17)	C10—C13	1.490 (2)
N1—C1	1.343 (2)	C11—C18	1.495 (2)
N1—C3	1.384 (2)	C12—C23	1.492 (2)
N1—H1N	0.90 (3)	C13—C17	1.391 (2)
N2—C1	1.317 (2)	C14—C15	1.390 (2)
N3—C7	1.359 (2)	C14—H14	0.9500
N3—H2N	0.86 (2)	C15—C16	1.383 (3)
N3—H3N	0.89 (2)	C15—H15	0.9500
C2—C3	1.326 (3)	C16—C17	1.388 (2)
C2—H2	0.9500	C16—H16	0.9500
C3—H3	0.9500	C17—H17	0.9500
C4—C5	1.392 (2)	C18—C22	1.393 (2)
C4—C9	1.397 (2)	C19—C20	1.385 (3)
C5—C6	1.381 (2)	C19—H19	0.9500
C5—H5	0.9500	C20—C21	1.379 (3)
C6—C7	1.407 (2)	C20—H20	0.9500
C6—H6	0.9500	C21—C22	1.388 (2)
C7—C8	1.411 (2)	C21—H21	0.9500
C8—C9	1.372 (2)	C22—H22	0.9500
C8—H8	0.9500	C23—C27	1.388 (2)
C9—H9	0.9500	C24—C25	1.385 (3)
N4—C11	1.341 (2)	C24—H24	0.9500
N4—C10	1.341 (2)	C25—C26	1.382 (3)
N5—C12	1.337 (2)	C25—H25	0.9500
N5—C11	1.341 (2)	C26—C27	1.389 (3)
N6—C12	1.337 (2)	C26—H26	0.9500
N6—C10	1.338 (2)	C27—H27	0.9500
N7—C14	1.338 (2)
C2—S1—C1	91.05 (9)	N4—C11—C18	118.45 (15)
O2—S2—O1	117.20 (8)	N5—C11—C18	116.06 (15)
O2—S2—N2	105.59 (8)	N6—C12—N5	125.13 (15)
O1—S2—N2	111.61 (8)	N6—C12—C23	116.30 (15)
O2—S2—C4	108.79 (8)	N5—C12—C23	118.56 (15)
O1—S2—C4	108.12 (8)	N7—C13—C17	122.90 (16)
N2—S2—C4	104.82 (8)	N7—C13—C10	117.34 (15)
C1—N1—C3	115.58 (16)	C17—C13—C10	119.76 (15)
C1—N1—H1N	123.4 (16)	N7—C14—C15	123.83 (16)
C3—N1—H1N	120.9 (16)	N7—C14—H14	118.1
C1—N2—S2	119.62 (12)	C15—C14—H14	118.1
C7—N3—H2N	121.0 (14)	C16—C15—C14	118.37 (16)
C7—N3—H3N	120.2 (14)	C16—C15—H15	120.8
H2N—N3—H3N	115 (2)	C14—C15—H15	120.8
N2—C1—N1	121.27 (15)	C15—C16—C17	118.85 (16)
N2—C1—S1	129.99 (13)	C15—C16—H16	120.6
N1—C1—S1	108.72 (13)	C17—C16—H16	120.6
C3—C2—S1	111.04 (16)	C16—C17—C13	118.88 (16)
C3—C2—H2	124.5	C16—C17—H17	120.6
S1—C2—H2	124.5	C13—C17—H17	120.6
C2—C3—N1	113.58 (18)	N8—C18—C22	122.68 (16)
C2—C3—H3	123.2	N8—C18—C11	117.51 (15)
N1—C3—H3	123.2	C22—C18—C11	119.80 (15)
C5—C4—C9	119.38 (15)	N8—C19—C20	123.98 (17)
C5—C4—S2	121.31 (13)	N8—C19—H19	118.0
C9—C4—S2	119.07 (13)	C20—C19—H19	118.0
C6—C5—C4	120.18 (16)	C21—C20—C19	118.51 (17)
C6—C5—H5	119.9	C21—C20—H20	120.7
C4—C5—H5	119.9	C19—C20—H20	120.7
C5—C6—C7	121.20 (16)	C20—C21—C22	118.67 (17)
C5—C6—H6	119.4	C20—C21—H21	120.7
C7—C6—H6	119.4	C22—C21—H21	120.7
N3—C7—C6	121.83 (16)	C21—C22—C18	118.91 (17)
N3—C7—C8	120.52 (16)	C21—C22—H22	120.5
C6—C7—C8	117.64 (15)	C18—C22—H22	120.5
C9—C8—C7	121.02 (16)	N9—C23—C27	122.59 (16)
C9—C8—H8	119.5	N9—C23—C12	116.79 (15)
C7—C8—H8	119.5	C27—C23—C12	120.61 (16)
C8—C9—C4	120.57 (16)	N9—C24—C25	123.73 (17)
C8—C9—H9	119.7	N9—C24—H24	118.1
C4—C9—H9	119.7	C25—C24—H24	118.1
C11—N4—C10	114.23 (14)	C26—C25—C24	118.44 (17)
C12—N5—C11	114.75 (15)	C26—C25—H25	120.8
C12—N6—C10	114.91 (15)	C24—C25—H25	120.8
C14—N7—C13	117.16 (15)	C25—C26—C27	118.78 (18)
C19—N8—C18	117.21 (16)	C25—C26—H26	120.6
C24—N9—C23	117.49 (16)	C27—C26—H26	120.6
N6—C10—N4	125.46 (16)	C23—C27—C26	118.97 (17)
N6—C10—C13	115.56 (15)	C23—C27—H27	120.5
N4—C10—C13	118.97 (15)	C26—C27—H27	120.5
N4—C11—N5	125.49 (15)
O2—S2—N2—C1	167.64 (13)	C11—N5—C12—N6	0.7 (2)
O1—S2—N2—C1	39.26 (16)	C11—N5—C12—C23	−179.92 (15)
C4—S2—N2—C1	−77.54 (15)	C14—N7—C13—C17	−1.2 (2)
S2—N2—C1—N1	167.95 (13)	C14—N7—C13—C10	178.86 (15)
S2—N2—C1—S1	−13.5 (2)	N6—C10—C13—N7	−162.39 (15)
C3—N1—C1—N2	179.67 (17)	N4—C10—C13—N7	18.1 (2)
C3—N1—C1—S1	0.9 (2)	N6—C10—C13—C17	17.7 (2)
C2—S1—C1—N2	179.95 (18)	N4—C10—C13—C17	−161.75 (16)
C2—S1—C1—N1	−1.38 (15)	C13—N7—C14—C15	0.5 (3)
C1—S1—C2—C3	1.62 (19)	N7—C14—C15—C16	0.9 (3)
S1—C2—C3—N1	−1.4 (3)	C14—C15—C16—C17	−1.5 (3)
C1—N1—C3—C2	0.4 (3)	C15—C16—C17—C13	0.8 (3)
O2—S2—C4—C5	−140.37 (14)	N7—C13—C17—C16	0.6 (3)
O1—S2—C4—C5	−12.10 (17)	C10—C13—C17—C16	−179.51 (16)
N2—S2—C4—C5	107.07 (15)	C19—N8—C18—C22	2.0 (3)
O2—S2—C4—C9	45.36 (16)	C19—N8—C18—C11	−176.87 (16)
O1—S2—C4—C9	173.63 (13)	N4—C11—C18—N8	−6.3 (2)
N2—S2—C4—C9	−67.20 (15)	N5—C11—C18—N8	173.32 (15)
C9—C4—C5—C6	0.1 (3)	N4—C11—C18—C22	174.83 (16)
S2—C4—C5—C6	−174.18 (14)	N5—C11—C18—C22	−5.6 (2)
C4—C5—C6—C7	1.0 (3)	C18—N8—C19—C20	−0.5 (3)
C5—C6—C7—N3	179.31 (17)	N8—C19—C20—C21	−1.0 (3)
C5—C6—C7—C8	−1.2 (3)	C19—C20—C21—C22	1.0 (3)
N3—C7—C8—C9	179.96 (16)	C20—C21—C22—C18	0.4 (3)
C6—C7—C8—C9	0.5 (3)	N8—C18—C22—C21	−2.0 (3)
C7—C8—C9—C4	0.5 (3)	C11—C18—C22—C21	176.84 (16)
C5—C4—C9—C8	−0.8 (3)	C24—N9—C23—C27	0.5 (3)
S2—C4—C9—C8	173.57 (14)	C24—N9—C23—C12	−178.59 (16)
C12—N6—C10—N4	−1.4 (2)	N6—C12—C23—N9	175.31 (15)
C12—N6—C10—C13	179.14 (14)	N5—C12—C23—N9	−4.1 (2)
C11—N4—C10—N6	0.7 (2)	N6—C12—C23—C27	−3.8 (2)
C11—N4—C10—C13	−179.88 (14)	N5—C12—C23—C27	176.81 (17)
C10—N4—C11—N5	0.9 (2)	C23—N9—C24—C25	0.2 (3)
C10—N4—C11—C18	−179.52 (15)	N9—C24—C25—C26	−0.4 (3)
C12—N5—C11—N4	−1.6 (2)	C24—C25—C26—C27	−0.1 (3)
C12—N5—C11—C18	178.84 (14)	N9—C23—C27—C26	−1.0 (3)
C10—N6—C12—N5	0.7 (2)	C12—C23—C27—C26	178.08 (17)
C10—N6—C12—C23	−178.71 (15)	C25—C26—C27—C23	0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N9i	0.90 (3)	1.98 (3)	2.835 (3)	158 (2)
N3—H2N···N8ii	0.85 (3)	2.13 (3)	2.983 (3)	174 (2)
N3—H3N···N7ii	0.89 (2)	2.13 (2)	3.010 (2)	171 (3)
C2—H2···O2iii	0.95	2.37	3.237 (3)	151
C16—H16···O2iv	0.95	2.50	3.331 (2)	145
C20—H20···O1v	0.95	2.48	3.156 (3)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N9i	0.90 (3)	1.98 (3)	2.835 (3)	158 (2)
N3—H2N⋯N8ii	0.85 (3)	2.13 (3)	2.983 (3)	174 (2)
N3—H3N⋯N7ii	0.89 (2)	2.13 (2)	3.010 (2)	171 (3)
C2—H2⋯O2iii	0.95	2.37	3.237 (3)	151
C16—H16⋯O2iv	0.95	2.50	3.331 (2)	145
C20—H20⋯O1v	0.95	2.48	3.156 (3)	128

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