4-[3-(1-Naphthyl-oxymeth-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-6-yl]-3-p-tolyl-sydnone.

In the title sydnone compound, C(24)H(18)N(6)O(3)S {systematic name: 4-[3-(1-naphthyl-oxymeth-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-6-yl]-3-p-tolyl-4,5-dihydro-1,2,3-oxadiazol-3-ium-5-olate} an intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. The 3,6-dihydro-1,3,4-thia-diazine ring adopts a twist-boat conformation. The essentially planar 1,2,3-oxadiazole and 1,2,4-triazole rings [maximum deviations of 0.006 (1) and 0.008 (1) Å, respectively] are inclined to one another at inter-planar angle of 44.11 (4)°. The naphthalene unit forms an inter-planar angle of 66.40 (4)° with the 1,2,4-triazole ring. In the crystal packing, pairs of inter-molecular C-H⋯O hydrogen bonds link adjacent mol-ecules into dimers incorporating R(2) (2)(12) ring motifs. Further stabilization is provided by weak C-H⋯π inter-actions.

Related literature

For general background to and applications of the title sydnone compound, see: Baker et al. (1949 ▶); Hedge et al. (2008 ▶); Rai et al. (2008 ▶). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Baker & Ollis (1957 ▶); Goh et al. (2010 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C24H18N6O3S

M = 470.50

Monoclinic,

a = 21.6096 (8) Å

b = 8.3622 (3) Å

c = 11.9272 (4) Å

β = 94.694 (1)°

V = 2148.06 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 100 K

0.82 × 0.28 × 0.22 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.857, T max = 0.959

30407 measured reflections

9432 independent reflections

8048 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.110

S = 1.08

9432 reflections

379 parameters

All H-atom parameters refined

Δρmax = 0.58 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017812/lh5045sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017812/lh5045Isup2.hkl

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

C24H18N6O3S	F(000) = 976
Mr = 470.50	Dx = 1.455 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9918 reflections
a = 21.6096 (8) Å	θ = 2.6–35.1°
b = 8.3622 (3) Å	µ = 0.19 mm−1
c = 11.9272 (4) Å	T = 100 K
β = 94.694 (1)°	Block, colourless
V = 2148.06 (13) Å3	0.82 × 0.28 × 0.22 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	9432 independent reflections
Radiation source: fine-focus sealed tube	8048 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 35.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −34→34
Tmin = 0.857, Tmax = 0.959	k = −13→11
30407 measured reflections	l = −19→17

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	All H-atom parameters refined
S = 1.08	w = 1/[σ2(Fo2) + (0.0621P)2 + 0.4207P] where P = (Fo2 + 2Fc2)/3
9432 reflections	(Δ/σ)max = 0.001
379 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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. 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 > 2sigma(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	0.054237 (8)	0.64796 (2)	0.368050 (17)	0.01458 (5)
O1	0.25803 (3)	0.72732 (8)	0.06654 (5)	0.01628 (11)
O2	0.09850 (3)	1.30606 (7)	0.46932 (5)	0.01662 (11)
O3	0.00745 (3)	1.17152 (8)	0.43365 (5)	0.01799 (11)
N1	0.14829 (3)	0.50393 (9)	0.12173 (6)	0.01643 (12)
N2	0.11061 (3)	0.46927 (8)	0.20910 (6)	0.01603 (12)
N3	0.12737 (3)	0.72984 (8)	0.20468 (6)	0.01263 (11)
N4	0.13693 (3)	0.88576 (8)	0.24115 (6)	0.01300 (11)
N5	0.15806 (3)	1.29814 (8)	0.43898 (6)	0.01614 (12)
N6	0.15941 (3)	1.17335 (8)	0.37354 (5)	0.01269 (11)
C1	0.35987 (4)	0.77223 (11)	0.01602 (7)	0.01752 (14)
C2	0.38308 (4)	0.65856 (13)	0.09650 (8)	0.02498 (18)
C3	0.44556 (5)	0.62503 (19)	0.10958 (11)	0.0366 (3)
C4	0.48733 (5)	0.7049 (2)	0.04353 (11)	0.0389 (3)
C5	0.46585 (5)	0.81610 (17)	−0.03400 (10)	0.0320 (2)
C6	0.40179 (4)	0.85376 (12)	−0.05035 (8)	0.02161 (16)
C7	0.37898 (5)	0.97005 (13)	−0.12929 (8)	0.02567 (18)
C8	0.31662 (5)	0.99837 (12)	−0.14608 (8)	0.02419 (17)
C9	0.27387 (4)	0.91590 (10)	−0.08351 (7)	0.01914 (14)
C10	0.29522 (4)	0.80784 (10)	−0.00217 (7)	0.01503 (13)
C11	0.19294 (3)	0.75150 (10)	0.04109 (7)	0.01550 (13)
C12	0.15819 (3)	0.65872 (9)	0.12197 (7)	0.01378 (12)
C13	0.09846 (3)	0.60679 (9)	0.25608 (7)	0.01354 (12)
C14	0.03560 (3)	0.85027 (9)	0.31981 (7)	0.01418 (12)
C15	0.09438 (3)	0.94058 (9)	0.30182 (6)	0.01176 (11)
C16	0.10454 (3)	1.09342 (9)	0.35705 (6)	0.01216 (11)
C17	0.06224 (4)	1.18116 (9)	0.41931 (6)	0.01406 (12)
C18	0.21821 (3)	1.14204 (9)	0.32812 (6)	0.01316 (12)
C19	0.22339 (4)	1.16937 (10)	0.21476 (7)	0.01628 (13)
C20	0.28120 (4)	1.14737 (11)	0.17364 (7)	0.01943 (15)
C21	0.33262 (4)	1.10009 (11)	0.24445 (8)	0.02073 (15)
C22	0.32506 (4)	1.07116 (11)	0.35765 (8)	0.02126 (15)
C23	0.26765 (4)	1.09216 (10)	0.40109 (7)	0.01746 (14)
C24	0.39559 (5)	1.08553 (16)	0.19990 (11)	0.0326 (2)
H2A	0.3546 (7)	0.602 (2)	0.1375 (14)	0.036 (4)*
H3A	0.4629 (9)	0.548 (3)	0.1663 (17)	0.056 (5)*
H4A	0.5305 (9)	0.677 (3)	0.0521 (16)	0.053 (5)*
H5A	0.4945 (7)	0.876 (2)	−0.0788 (14)	0.033 (4)*
H7A	0.4102 (7)	1.029 (2)	−0.1753 (13)	0.035 (4)*
H8A	0.3011 (7)	1.076 (2)	−0.2028 (14)	0.038 (4)*
H9A	0.2288 (6)	0.9413 (19)	−0.0985 (11)	0.024 (3)*
H11A	0.1812 (6)	0.7163 (18)	−0.0368 (11)	0.020 (3)*
H11B	0.1818 (6)	0.8606 (17)	0.0462 (12)	0.021 (3)*
H14A	0.0118 (6)	0.8427 (17)	0.2483 (12)	0.020 (3)*
H14B	0.0114 (6)	0.8965 (17)	0.3770 (11)	0.017 (3)*
H19A	0.1867 (6)	1.1991 (18)	0.1683 (12)	0.022 (3)*
H20A	0.2844 (7)	1.1636 (18)	0.0939 (13)	0.026 (3)*
H22A	0.3595 (7)	1.039 (2)	0.4079 (12)	0.029 (4)*
H23A	0.2619 (6)	1.0695 (19)	0.4794 (12)	0.026 (3)*
H24A	0.4217 (10)	1.175 (3)	0.2286 (18)	0.059 (6)*
H24B	0.4133 (8)	0.985 (3)	0.2221 (16)	0.049 (5)*
H24C	0.3950 (8)	1.088 (3)	0.1166 (16)	0.048 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.01306 (8)	0.01134 (8)	0.01984 (9)	−0.00084 (5)	0.00436 (6)	0.00005 (6)
O1	0.0125 (2)	0.0195 (3)	0.0170 (2)	0.00011 (19)	0.00242 (18)	0.0030 (2)
O2	0.0204 (2)	0.0124 (2)	0.0174 (3)	0.00013 (19)	0.00400 (19)	−0.00343 (19)
O3	0.0160 (2)	0.0173 (3)	0.0211 (3)	0.00308 (19)	0.0046 (2)	−0.0018 (2)
N1	0.0154 (3)	0.0131 (3)	0.0211 (3)	0.0009 (2)	0.0029 (2)	−0.0035 (2)
N2	0.0145 (2)	0.0116 (3)	0.0221 (3)	0.0004 (2)	0.0027 (2)	−0.0025 (2)
N3	0.0116 (2)	0.0099 (2)	0.0166 (3)	−0.00056 (18)	0.00252 (19)	−0.0028 (2)
N4	0.0138 (2)	0.0095 (2)	0.0160 (3)	−0.00074 (19)	0.0026 (2)	−0.0023 (2)
N5	0.0197 (3)	0.0124 (3)	0.0165 (3)	−0.0018 (2)	0.0026 (2)	−0.0030 (2)
N6	0.0151 (2)	0.0103 (2)	0.0127 (2)	−0.00127 (19)	0.00128 (19)	−0.00056 (19)
C1	0.0156 (3)	0.0205 (4)	0.0168 (3)	−0.0006 (3)	0.0035 (2)	0.0003 (3)
C2	0.0160 (3)	0.0350 (5)	0.0239 (4)	0.0015 (3)	0.0015 (3)	0.0093 (4)
C3	0.0175 (4)	0.0562 (8)	0.0361 (5)	0.0061 (4)	0.0015 (4)	0.0177 (5)
C4	0.0160 (4)	0.0603 (8)	0.0409 (6)	0.0026 (4)	0.0059 (4)	0.0126 (6)
C5	0.0191 (4)	0.0453 (6)	0.0330 (5)	−0.0026 (4)	0.0101 (3)	0.0052 (5)
C6	0.0192 (3)	0.0255 (4)	0.0211 (4)	−0.0014 (3)	0.0076 (3)	0.0003 (3)
C7	0.0299 (4)	0.0239 (4)	0.0250 (4)	−0.0017 (3)	0.0131 (3)	0.0031 (3)
C8	0.0317 (4)	0.0186 (4)	0.0238 (4)	0.0049 (3)	0.0116 (3)	0.0057 (3)
C9	0.0232 (3)	0.0163 (3)	0.0187 (3)	0.0054 (3)	0.0064 (3)	0.0023 (3)
C10	0.0163 (3)	0.0147 (3)	0.0145 (3)	0.0004 (2)	0.0043 (2)	−0.0007 (2)
C11	0.0135 (3)	0.0165 (3)	0.0167 (3)	0.0022 (2)	0.0025 (2)	−0.0007 (2)
C12	0.0127 (3)	0.0127 (3)	0.0161 (3)	0.0013 (2)	0.0021 (2)	−0.0032 (2)
C13	0.0108 (2)	0.0109 (3)	0.0189 (3)	−0.0006 (2)	0.0010 (2)	−0.0012 (2)
C14	0.0111 (3)	0.0116 (3)	0.0199 (3)	0.0005 (2)	0.0022 (2)	−0.0014 (2)
C15	0.0114 (2)	0.0099 (3)	0.0140 (3)	0.0004 (2)	0.0010 (2)	−0.0006 (2)
C16	0.0130 (3)	0.0099 (3)	0.0138 (3)	−0.0001 (2)	0.0023 (2)	−0.0011 (2)
C17	0.0171 (3)	0.0111 (3)	0.0142 (3)	0.0018 (2)	0.0023 (2)	−0.0007 (2)
C18	0.0131 (3)	0.0115 (3)	0.0149 (3)	−0.0018 (2)	0.0018 (2)	−0.0002 (2)
C19	0.0180 (3)	0.0167 (3)	0.0142 (3)	−0.0019 (2)	0.0018 (2)	−0.0010 (2)
C20	0.0211 (3)	0.0196 (4)	0.0182 (3)	−0.0039 (3)	0.0059 (3)	−0.0048 (3)
C21	0.0164 (3)	0.0175 (3)	0.0289 (4)	−0.0023 (3)	0.0054 (3)	−0.0079 (3)
C22	0.0153 (3)	0.0194 (4)	0.0286 (4)	−0.0002 (3)	−0.0009 (3)	0.0002 (3)
C23	0.0169 (3)	0.0162 (3)	0.0189 (3)	−0.0019 (2)	−0.0010 (2)	0.0029 (3)
C24	0.0192 (4)	0.0360 (6)	0.0440 (6)	−0.0028 (4)	0.0112 (4)	−0.0160 (5)

S1—C13	1.7390 (8)	C7—C8	1.3667 (14)
S1—C14	1.8214 (8)	C7—H7A	1.028 (16)
O1—C10	1.3707 (10)	C8—C9	1.4138 (12)
O1—C11	1.4289 (9)	C8—H8A	0.980 (17)
O2—N5	1.3667 (9)	C9—C10	1.3775 (12)
O2—C17	1.4086 (10)	C9—H9A	0.998 (14)
O3—C17	1.2126 (9)	C11—C12	1.4882 (11)
N1—C12	1.3119 (10)	C11—H11A	0.988 (14)
N1—N2	1.4044 (10)	C11—H11B	0.946 (14)
N2—C13	1.3151 (10)	C14—C15	1.5080 (10)
N3—C12	1.3704 (10)	C14—H14A	0.962 (14)
N3—C13	1.3739 (10)	C14—H14B	0.974 (13)
N3—N4	1.3846 (9)	C15—C16	1.4464 (10)
N4—C15	1.2994 (9)	C16—C17	1.4272 (10)
N5—N6	1.3049 (9)	C18—C19	1.3849 (11)
N6—C16	1.3612 (9)	C18—C23	1.3860 (11)
N6—C18	1.4454 (10)	C19—C20	1.3910 (12)
C1—C2	1.4134 (13)	C19—H19A	0.962 (14)
C1—C6	1.4246 (12)	C20—C21	1.3967 (13)
C1—C10	1.4275 (11)	C20—H20A	0.969 (15)
C2—C3	1.3752 (13)	C21—C22	1.3943 (14)
C2—H2A	0.945 (17)	C21—C24	1.5058 (13)
C3—C4	1.4134 (16)	C22—C23	1.3941 (12)
C3—H3A	0.99 (2)	C22—H22A	0.954 (15)
C4—C5	1.3659 (18)	C23—H23A	0.971 (14)
C4—H4A	0.96 (2)	C24—H24A	0.98 (2)
C5—C6	1.4174 (14)	C24—H24B	0.96 (2)
C5—H5A	0.986 (16)	C24—H24C	0.993 (19)
C6—C7	1.4139 (14)
C13—S1—C14	93.58 (4)	C12—C11—H11B	108.4 (8)
C10—O1—C11	114.75 (6)	H11A—C11—H11B	107.5 (12)
N5—O2—C17	110.81 (6)	N1—C12—N3	109.94 (7)
C12—N1—N2	107.84 (6)	N1—C12—C11	127.14 (7)
C13—N2—N1	106.48 (6)	N3—C12—C11	122.76 (7)
C12—N3—C13	105.17 (6)	N2—C13—N3	110.54 (7)
C12—N3—N4	124.47 (6)	N2—C13—S1	129.92 (6)
C13—N3—N4	128.81 (6)	N3—C13—S1	119.53 (6)
C15—N4—N3	114.39 (6)	C15—C14—S1	110.06 (5)
N6—N5—O2	105.36 (6)	C15—C14—H14A	107.6 (8)
N5—N6—C16	114.66 (6)	S1—C14—H14A	107.9 (8)
N5—N6—C18	115.62 (6)	C15—C14—H14B	114.1 (8)
C16—N6—C18	129.71 (6)	S1—C14—H14B	105.4 (8)
C2—C1—C6	119.52 (8)	H14A—C14—H14B	111.6 (11)
C2—C1—C10	122.14 (8)	N4—C15—C16	118.51 (6)
C6—C1—C10	118.34 (8)	N4—C15—C14	123.04 (7)
C3—C2—C1	120.31 (9)	C16—C15—C14	118.43 (6)
C3—C2—H2A	121.0 (10)	N6—C16—C17	105.06 (6)
C1—C2—H2A	118.6 (10)	N6—C16—C15	126.71 (6)
C2—C3—C4	120.42 (11)	C17—C16—C15	127.69 (6)
C2—C3—H3A	121.6 (11)	O3—C17—O2	120.35 (7)
C4—C3—H3A	117.9 (11)	O3—C17—C16	135.53 (7)
C5—C4—C3	120.13 (10)	O2—C17—C16	104.10 (6)
C5—C4—H4A	120.8 (12)	C19—C18—C23	122.88 (7)
C3—C4—H4A	119.1 (12)	C19—C18—N6	118.68 (7)
C4—C5—C6	121.22 (9)	C23—C18—N6	118.38 (7)
C4—C5—H5A	121.1 (10)	C18—C19—C20	117.98 (7)
C6—C5—H5A	117.6 (10)	C18—C19—H19A	118.5 (8)
C7—C6—C5	121.86 (9)	C20—C19—H19A	123.5 (8)
C7—C6—C1	119.75 (8)	C19—C20—C21	121.14 (8)
C5—C6—C1	118.39 (9)	C19—C20—H20A	117.8 (9)
C8—C7—C6	120.17 (8)	C21—C20—H20A	121.0 (9)
C8—C7—H7A	121.4 (9)	C22—C21—C20	118.96 (8)
C6—C7—H7A	118.4 (9)	C22—C21—C24	120.57 (9)
C7—C8—C9	121.15 (9)	C20—C21—C24	120.44 (9)
C7—C8—H8A	119.6 (9)	C23—C22—C21	121.09 (8)
C9—C8—H8A	119.2 (9)	C23—C22—H22A	118.3 (8)
C10—C9—C8	119.73 (8)	C21—C22—H22A	120.6 (8)
C10—C9—H9A	122.1 (8)	C18—C23—C22	117.92 (8)
C8—C9—H9A	118.1 (8)	C18—C23—H23A	120.7 (8)
O1—C10—C9	124.35 (7)	C22—C23—H23A	121.4 (8)
O1—C10—C1	114.90 (7)	C21—C24—H24A	108.9 (12)
C9—C10—C1	120.74 (7)	C21—C24—H24B	109.1 (11)
O1—C11—C12	109.19 (6)	H24A—C24—H24B	111.9 (16)
O1—C11—H11A	109.2 (8)	C21—C24—H24C	114.4 (10)
C12—C11—H11A	110.5 (8)	H24A—C24—H24C	107.1 (17)
O1—C11—H11B	112.0 (8)	H24B—C24—H24C	105.4 (16)
C12—N1—N2—C13	1.48 (8)	C12—N3—C13—N2	0.23 (8)
C12—N3—N4—C15	165.86 (7)	N4—N3—C13—N2	−165.83 (7)
C13—N3—N4—C15	−30.53 (10)	C12—N3—C13—S1	179.55 (5)
C17—O2—N5—N6	−0.43 (8)	N4—N3—C13—S1	13.50 (10)
O2—N5—N6—C16	−0.38 (9)	C14—S1—C13—N2	−153.37 (8)
O2—N5—N6—C18	178.66 (6)	C14—S1—C13—N3	27.46 (6)
C6—C1—C2—C3	−0.97 (16)	C13—S1—C14—C15	−53.80 (6)
C10—C1—C2—C3	178.48 (11)	N3—N4—C15—C16	171.38 (6)
C1—C2—C3—C4	0.6 (2)	N3—N4—C15—C14	−6.97 (10)
C2—C3—C4—C5	0.0 (2)	S1—C14—C15—N4	51.78 (9)
C3—C4—C5—C6	−0.2 (2)	S1—C14—C15—C16	−126.57 (6)
C4—C5—C6—C7	179.19 (13)	N5—N6—C16—C17	1.00 (9)
C4—C5—C6—C1	−0.20 (18)	C18—N6—C16—C17	−177.88 (7)
C2—C1—C6—C7	−178.65 (9)	N5—N6—C16—C15	−171.03 (7)
C10—C1—C6—C7	1.88 (13)	C18—N6—C16—C15	10.09 (12)
C2—C1—C6—C5	0.75 (14)	N4—C15—C16—N6	−15.34 (11)
C10—C1—C6—C5	−178.72 (9)	C14—C15—C16—N6	163.09 (7)
C5—C6—C7—C8	177.25 (11)	N4—C15—C16—C17	174.40 (7)
C1—C6—C7—C8	−3.36 (15)	C14—C15—C16—C17	−7.18 (11)
C6—C7—C8—C9	1.64 (16)	N5—O2—C17—O3	−177.66 (7)
C7—C8—C9—C10	1.61 (15)	N5—O2—C17—C16	1.00 (8)
C11—O1—C10—C9	5.75 (11)	N6—C16—C17—O3	177.21 (9)
C11—O1—C10—C1	−174.30 (7)	C15—C16—C17—O3	−10.86 (15)
C8—C9—C10—O1	176.86 (8)	N6—C16—C17—O2	−1.15 (8)
C8—C9—C10—C1	−3.09 (13)	C15—C16—C17—O2	170.78 (7)
C2—C1—C10—O1	1.93 (12)	N5—N6—C18—C19	−108.58 (8)
C6—C1—C10—O1	−178.61 (7)	C16—N6—C18—C19	70.29 (11)
C2—C1—C10—C9	−178.12 (9)	N5—N6—C18—C23	68.82 (9)
C6—C1—C10—C9	1.34 (12)	C16—N6—C18—C23	−112.31 (9)
C10—O1—C11—C12	−179.64 (6)	C23—C18—C19—C20	−0.86 (12)
N2—N1—C12—N3	−1.37 (9)	N6—C18—C19—C20	176.42 (7)
N2—N1—C12—C11	−176.75 (7)	C18—C19—C20—C21	−0.37 (13)
C13—N3—C12—N1	0.74 (8)	C19—C20—C21—C22	1.50 (13)
N4—N3—C12—N1	167.57 (7)	C19—C20—C21—C24	−176.65 (9)
C13—N3—C12—C11	176.36 (7)	C20—C21—C22—C23	−1.45 (14)
N4—N3—C12—C11	−16.80 (11)	C24—C21—C22—C23	176.69 (9)
O1—C11—C12—N1	−76.16 (10)	C19—C18—C23—C22	0.90 (12)
O1—C11—C12—N3	109.01 (8)	N6—C18—C23—C22	−176.38 (7)
N1—N2—C13—N3	−1.03 (8)	C21—C22—C23—C18	0.29 (13)
N1—N2—C13—S1	179.73 (6)

Cg1 and Cg2 are the centroids of the C18–C23 and C1/C6–C10 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O3	0.973 (13)	2.401 (14)	3.0928 (10)	127.7 (10)
C14—H14B···O3i	0.973 (13)	2.396 (13)	3.1612 (10)	135.2 (11)
C8—H8A···Cg1ii	0.980 (17)	2.603 (17)	3.3928 (11)	138.0 (13)
C24—H24C···Cg2	0.993 (19)	2.95 (2)	3.7066 (14)	134.3 (17)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C18–C23 and C1/C6–C10 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯O3	0.973 (13)	2.401 (14)	3.0928 (10)	127.7 (10)
C14—H14B⋯O3i	0.973 (13)	2.396 (13)	3.1612 (10)	135.2 (11)
C8—H8A⋯Cg1ii	0.980 (17)	2.603 (17)	3.3928 (11)	138.0 (13)
C24—H24C⋯Cg2	0.993 (19)	2.95 (2)	3.7066 (14)	134.3 (17)

Symmetry codes: (i) ; (ii) .