1-[4-(Di-methyl-amino)-benzyl-idene]-4-o-tolyl-thio-semicarbazide.

The asymmetric unit of the title compound, C17H20N4S, contains two independent mol-ecules, the main difference between them being the dihedral angles between the benzene rings [19.99 (17) and 9.72 (17)°]. The mol-ecules both have a trans conformation about the C=N double bond and intra-molecular C-H⋯S and N-H⋯N hydrogen bonds are observed in both mol-ecules. In the crystal, mol-ecules are linked by weak N-H⋯S hydrogen bonds with graph-set motif R 2 (2)(8). In each mol-ecule, all but one of the N atoms and both the S atoms are involved in hydrogen bonding.

Related literature

For details of anion recognition, see: Sessler et al. (2006 ▶); Amendola et al. (2006 ▶); Fahlbusch et al. (2006 ▶); Gale & Quesada (2006 ▶); Perez & Riera (2008 ▶); Willans et al. (2009 ▶); Amendola & Fabbrizzi (2009 ▶); Haridas et al. (2012 ▶). For applications of thio­semicarbazides, see: Basuli et al. (1998 ▶); Pandeya et al. (1999 ▶); Kowol et al. (2010 ▶). For thio­semicarbazones acting as anion acceptors, see: Chikate et al. (2005 ▶); Krisitin (2005 ▶). For details of the synthesis of the Schiff base ligand, see: Pouralimardan et al. (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H20N4S

M = 312.43

Triclinic,

a = 9.172 (3) Å

b = 12.224 (4) Å

c = 15.563 (5) Å

α = 86.933 (6)°

β = 86.990 (7)°

γ = 70.382 (6)°

V = 1640.3 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 173 K

0.20 × 0.15 × 0.03 mm

Data collection

Brucker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick,2008 ▶) T min = 0.961, T max = 0.994

7929 measured reflections

5640 independent reflections

3127 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.155

S = 0.95

5640 reflections

419 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813012890/bx2440sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012890/bx2440Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012890/bx2440Isup3.mol

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012890/bx2440Isup4.cml

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

C17H20N4S	Z = 4
Mr = 312.43	F(000) = 664
Triclinic, P1	Dx = 1.265 Mg m−3
Hall symbol: -P 1	Melting point: 452 K
a = 9.172 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.224 (4) Å	Cell parameters from 9709 reflections
c = 15.563 (5) Å	θ = 1.8–25.0°
α = 86.933 (6)°	µ = 0.20 mm−1
β = 86.990 (7)°	T = 173 K
γ = 70.382 (6)°	Block, yellow
V = 1640.3 (9) Å3	0.20 × 0.15 × 0.03 mm

Brucker SMART APEX diffractometer	5640 independent reflections
Radiation source: fine-focus sealed tube	3127 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω scan	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick,2008)	h = −9→10
Tmin = 0.961, Tmax = 0.994	k = −14→14
7929 measured reflections	l = −18→15

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ2(Fo2) + (0.0697P)2] where P = (Fo2 + 2Fc2)/3
5640 reflections	(Δ/σ)max = 0.001
419 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.17 e Å−3
0 constraints

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
H4N	0.578 (4)	0.812 (3)	0.419 (2)	0.090 (12)*
S2	1.04941 (11)	0.49993 (7)	1.21135 (6)	0.0688 (3)
S1	0.71619 (13)	0.85281 (7)	0.21044 (6)	0.0790 (3)
N8	0.9444 (3)	0.4024 (2)	1.08541 (17)	0.0587 (7)
N6	0.7262 (3)	0.5924 (2)	1.04273 (16)	0.0592 (7)
N7	0.8225 (3)	0.5919 (2)	1.10796 (16)	0.0617 (7)
H7N	0.8092	0.6550	1.1341	0.074*
N3	0.7612 (3)	0.6926 (2)	0.33190 (16)	0.0667 (8)
H3N	0.8358	0.6518	0.2990	0.080*
N2	0.7239 (3)	0.6441 (2)	0.40899 (16)	0.0622 (7)
C3	0.7517 (4)	0.3395 (3)	0.6503 (2)	0.0591 (8)
C27	0.9379 (4)	0.4935 (3)	1.13162 (18)	0.0526 (8)
N4	0.5776 (3)	0.8602 (2)	0.36927 (18)	0.0651 (8)
C20	0.3119 (3)	0.7492 (3)	0.8192 (2)	0.0540 (8)
C8	0.7901 (4)	0.4768 (2)	0.50474 (19)	0.0548 (8)
C25	0.5234 (3)	0.7076 (2)	0.95183 (19)	0.0530 (8)
C23	0.3245 (4)	0.8396 (3)	0.8656 (2)	0.0591 (8)
H23A	0.2616	0.9154	0.8530	0.071*
C28	1.0406 (4)	0.2847 (3)	1.0853 (2)	0.0544 (8)
C10	0.6811 (4)	0.8030 (3)	0.3086 (2)	0.0600 (8)
C21	0.4065 (4)	0.6374 (3)	0.8423 (2)	0.0639 (9)
H21A	0.4001	0.5748	0.8132	0.077*
N5	0.2121 (3)	0.7702 (2)	0.75317 (19)	0.0726 (8)
C24	0.4275 (4)	0.8183 (2)	0.9290 (2)	0.0580 (8)
H24A	0.4340	0.8808	0.9583	0.070*
C9	0.8135 (4)	0.5414 (3)	0.4282 (2)	0.0614 (9)
C7	0.8969 (4)	0.3691 (3)	0.5240 (2)	0.0648 (9)
H7B	0.9836	0.3406	0.4874	0.078*
C26	0.6322 (4)	0.6915 (3)	1.0191 (2)	0.0576 (8)
C11	0.4741 (4)	0.9757 (3)	0.37105 (19)	0.0559 (8)
C22	0.5090 (4)	0.6176 (2)	0.9070 (2)	0.0619 (9)
H22A	0.5704	0.5418	0.9210	0.074*
C33	1.0155 (4)	0.2181 (3)	1.0214 (2)	0.0612 (9)
C6	0.8797 (4)	0.3028 (3)	0.5947 (2)	0.0635 (9)
H6B	0.9557	0.2315	0.6057	0.076*
N1	0.7278 (3)	0.2725 (2)	0.71832 (18)	0.0754 (8)
C16	0.3454 (4)	0.9972 (3)	0.42636 (19)	0.0617 (9)
C5	0.6640 (4)	0.5151 (3)	0.5611 (2)	0.0727 (10)
H5A	0.5900	0.5876	0.5505	0.087*
C4	0.6443 (4)	0.4499 (3)	0.6320 (2)	0.0758 (10)
H4B	0.5582	0.4793	0.6688	0.091*
C29	1.1542 (4)	0.2360 (3)	1.1439 (2)	0.0695 (9)
H29A	1.1705	0.2813	1.1861	0.083*
C14	0.2744 (4)	1.1999 (3)	0.3839 (2)	0.0814 (11)
H14A	0.2066	1.2757	0.3886	0.098*
C30	1.2434 (4)	0.1207 (3)	1.1403 (2)	0.0768 (10)
H30A	1.3192	0.0875	1.1803	0.092*
C15	0.2464 (4)	1.1115 (3)	0.4309 (2)	0.0777 (10)
H15A	0.1585	1.1280	0.4672	0.093*
C32	1.1080 (5)	0.1035 (3)	1.0189 (2)	0.0777 (11)
H32A	1.0941	0.0577	0.9763	0.093*
C31	1.2200 (5)	0.0552 (3)	1.0775 (3)	0.0832 (12)
H31A	1.2805	−0.0228	1.0746	0.100*
C13	0.4014 (4)	1.1774 (3)	0.3301 (2)	0.0771 (10)
H13A	0.4204	1.2373	0.2972	0.092*
C12	0.5015 (4)	1.0657 (3)	0.3246 (2)	0.0731 (10)
H12A	0.5897	1.0506	0.2886	0.088*
C2	0.8405 (4)	0.1598 (3)	0.7369 (2)	0.0862 (12)
H2B	0.8578	0.1132	0.6872	0.129*
H2C	0.8027	0.1222	0.7844	0.129*
H2D	0.9361	0.1689	0.7515	0.129*
C34	0.8908 (4)	0.2672 (3)	0.9584 (2)	0.0783 (10)
H34A	0.7927	0.2977	0.9888	0.117*
H34B	0.8883	0.2071	0.9218	0.117*
H34C	0.9111	0.3284	0.9240	0.117*
C19	0.1023 (4)	0.8841 (3)	0.7355 (2)	0.0801 (11)
H19A	0.0530	0.9171	0.7885	0.120*
H19B	0.0255	0.8780	0.6982	0.120*
H19C	0.1552	0.9330	0.7081	0.120*
C17	0.3151 (5)	0.9008 (3)	0.4802 (2)	0.0911 (12)
H17A	0.3184	0.8389	0.4439	0.137*
H17B	0.2147	0.9297	0.5085	0.137*
H17C	0.3927	0.8722	0.5225	0.137*
C18	0.2157 (4)	0.6813 (3)	0.6966 (2)	0.0889 (12)
H18A	0.3104	0.6605	0.6623	0.133*
H18B	0.1293	0.7093	0.6596	0.133*
H18C	0.2097	0.6143	0.7297	0.133*
C1	0.6037 (4)	0.3152 (3)	0.7806 (2)	0.0912 (12)
H1A	0.5071	0.3430	0.7521	0.137*
H1B	0.6180	0.3776	0.8101	0.137*
H1C	0.6029	0.2536	0.8214	0.137*
H8N	0.864 (3)	0.425 (2)	1.0437 (18)	0.062 (9)*
H9A	0.903 (3)	0.512 (2)	0.3926 (16)	0.041 (8)*
H26A	0.635 (4)	0.761 (3)	1.045 (2)	0.082 (11)*

	U11	U22	U33	U12	U13	U23
S2	0.0767 (6)	0.0649 (5)	0.0642 (6)	−0.0209 (5)	−0.0089 (4)	−0.0088 (4)
S1	0.1248 (9)	0.0507 (5)	0.0585 (6)	−0.0272 (5)	0.0087 (5)	−0.0021 (4)
N8	0.0627 (19)	0.0517 (16)	0.0603 (17)	−0.0157 (14)	−0.0058 (15)	−0.0080 (14)
N6	0.0618 (18)	0.0560 (17)	0.0585 (17)	−0.0181 (14)	−0.0022 (14)	−0.0015 (13)
N7	0.0688 (19)	0.0515 (16)	0.0644 (17)	−0.0178 (14)	−0.0060 (15)	−0.0105 (13)
N3	0.089 (2)	0.0469 (15)	0.0544 (16)	−0.0118 (14)	0.0088 (15)	0.0007 (13)
N2	0.078 (2)	0.0491 (16)	0.0560 (17)	−0.0172 (15)	−0.0005 (14)	0.0036 (13)
C3	0.074 (2)	0.0452 (18)	0.055 (2)	−0.0161 (17)	−0.0033 (18)	−0.0022 (15)
C27	0.056 (2)	0.0499 (18)	0.0516 (18)	−0.0180 (16)	0.0068 (15)	−0.0011 (15)
N4	0.078 (2)	0.0502 (16)	0.0579 (18)	−0.0105 (15)	0.0004 (15)	0.0052 (14)
C20	0.050 (2)	0.0517 (19)	0.058 (2)	−0.0142 (16)	0.0050 (16)	−0.0031 (15)
C8	0.066 (2)	0.0457 (17)	0.0501 (18)	−0.0146 (16)	−0.0012 (16)	−0.0036 (15)
C25	0.058 (2)	0.0464 (18)	0.0518 (19)	−0.0145 (16)	0.0065 (16)	−0.0031 (14)
C23	0.059 (2)	0.0453 (18)	0.063 (2)	−0.0063 (16)	0.0053 (17)	0.0054 (16)
C28	0.056 (2)	0.0527 (19)	0.0555 (19)	−0.0210 (17)	0.0090 (16)	0.0005 (16)
C10	0.075 (2)	0.0449 (18)	0.061 (2)	−0.0197 (17)	−0.0036 (18)	−0.0047 (16)
C21	0.071 (2)	0.0473 (19)	0.071 (2)	−0.0149 (17)	−0.0082 (19)	−0.0087 (16)
N5	0.070 (2)	0.0604 (18)	0.077 (2)	−0.0055 (15)	−0.0151 (16)	−0.0037 (15)
C24	0.064 (2)	0.0441 (18)	0.063 (2)	−0.0155 (16)	0.0108 (17)	−0.0079 (15)
C9	0.075 (3)	0.051 (2)	0.056 (2)	−0.0177 (19)	0.0027 (19)	−0.0048 (17)
C7	0.070 (2)	0.053 (2)	0.058 (2)	−0.0039 (18)	0.0071 (17)	−0.0050 (16)
C26	0.064 (2)	0.050 (2)	0.060 (2)	−0.0201 (18)	0.0066 (17)	−0.0069 (17)
C11	0.060 (2)	0.0527 (19)	0.0515 (19)	−0.0145 (17)	−0.0028 (16)	−0.0019 (15)
C22	0.062 (2)	0.0412 (17)	0.075 (2)	−0.0084 (16)	0.0012 (18)	−0.0022 (16)
C33	0.074 (2)	0.060 (2)	0.054 (2)	−0.0301 (19)	0.0160 (17)	−0.0107 (16)
C6	0.068 (2)	0.0466 (18)	0.060 (2)	0.0018 (16)	0.0001 (17)	−0.0012 (16)
N1	0.089 (2)	0.0561 (17)	0.0674 (19)	−0.0107 (16)	0.0108 (17)	0.0104 (14)
C16	0.073 (2)	0.064 (2)	0.0496 (19)	−0.0246 (19)	−0.0016 (17)	−0.0051 (16)
C5	0.076 (3)	0.0494 (19)	0.074 (2)	0.0017 (18)	0.001 (2)	0.0050 (18)
C4	0.073 (2)	0.061 (2)	0.072 (2)	0.0006 (19)	0.0183 (19)	0.0071 (18)
C29	0.072 (2)	0.058 (2)	0.076 (2)	−0.0192 (19)	0.001 (2)	−0.0033 (18)
C14	0.084 (3)	0.061 (2)	0.083 (3)	−0.003 (2)	0.008 (2)	−0.006 (2)
C30	0.071 (3)	0.066 (2)	0.083 (3)	−0.011 (2)	0.007 (2)	0.005 (2)
C15	0.070 (3)	0.076 (3)	0.076 (3)	−0.012 (2)	0.0144 (19)	−0.013 (2)
C32	0.101 (3)	0.066 (2)	0.067 (2)	−0.030 (2)	0.022 (2)	−0.0169 (19)
C31	0.101 (3)	0.055 (2)	0.086 (3)	−0.020 (2)	0.033 (3)	−0.009 (2)
C13	0.086 (3)	0.057 (2)	0.080 (3)	−0.016 (2)	0.012 (2)	−0.0020 (18)
C12	0.072 (2)	0.059 (2)	0.078 (2)	−0.0108 (19)	0.0117 (19)	0.0023 (18)
C2	0.119 (3)	0.063 (2)	0.061 (2)	−0.012 (2)	−0.003 (2)	0.0100 (18)
C34	0.101 (3)	0.086 (2)	0.062 (2)	−0.050 (2)	0.003 (2)	−0.0141 (19)
C19	0.066 (2)	0.074 (2)	0.092 (3)	−0.012 (2)	−0.014 (2)	0.010 (2)
C17	0.103 (3)	0.092 (3)	0.083 (3)	−0.041 (2)	0.019 (2)	−0.005 (2)
C18	0.090 (3)	0.086 (3)	0.089 (3)	−0.023 (2)	−0.024 (2)	−0.007 (2)
C1	0.089 (3)	0.095 (3)	0.079 (3)	−0.021 (2)	0.009 (2)	0.015 (2)

S2—C27	1.670 (3)	C22—H22A	0.9300
S1—C10	1.670 (3)	C33—C32	1.374 (4)
N8—C27	1.340 (4)	C33—C34	1.491 (4)
N8—C28	1.413 (4)	C6—H6B	0.9300
N8—H8N	0.97 (3)	N1—C1	1.430 (4)
N6—C26	1.277 (4)	N1—C2	1.443 (4)
N6—N7	1.379 (3)	C16—C15	1.391 (4)
N7—C27	1.357 (4)	C16—C17	1.503 (4)
N7—H7N	0.8600	C5—C4	1.367 (4)
N3—C10	1.343 (3)	C5—H5A	0.9300
N3—N2	1.388 (3)	C4—H4B	0.9300
N3—H3N	0.8600	C29—C30	1.375 (4)
N2—C9	1.279 (4)	C29—H29A	0.9300
C3—N1	1.358 (4)	C14—C13	1.357 (5)
C3—C6	1.382 (4)	C14—C15	1.361 (4)
C3—C4	1.402 (4)	C14—H14A	0.9300
N4—C10	1.347 (4)	C30—C31	1.365 (5)
N4—C11	1.414 (4)	C30—H30A	0.9300
N4—H4N	0.94 (3)	C15—H15A	0.9300
C20—N5	1.369 (4)	C32—C31	1.367 (5)
C20—C21	1.391 (4)	C32—H32A	0.9300
C20—C23	1.391 (4)	C31—H31A	0.9300
C8—C5	1.378 (4)	C13—C12	1.371 (4)
C8—C7	1.381 (4)	C13—H13A	0.9300
C8—C9	1.440 (4)	C12—H12A	0.9300
C25—C22	1.379 (4)	C2—H2B	0.9600
C25—C24	1.383 (4)	C2—H2C	0.9600
C25—C26	1.445 (4)	C2—H2D	0.9600
C23—C24	1.356 (4)	C34—H34A	0.9600
C23—H23A	0.9300	C34—H34B	0.9600
C28—C29	1.378 (4)	C34—H34C	0.9600
C28—C33	1.393 (4)	C19—H19A	0.9600
C21—C22	1.370 (4)	C19—H19B	0.9600
C21—H21A	0.9300	C19—H19C	0.9600
N5—C18	1.426 (4)	C17—H17A	0.9600
N5—C19	1.440 (4)	C17—H17B	0.9600
C24—H24A	0.9300	C17—H17C	0.9600
C9—H9A	0.94 (2)	C18—H18A	0.9600
C7—C6	1.366 (4)	C18—H18B	0.9600
C7—H7B	0.9300	C18—H18C	0.9600
C26—H26A	0.97 (3)	C1—H1A	0.9600
C11—C12	1.370 (4)	C1—H1B	0.9600
C11—C16	1.383 (4)	C1—H1C	0.9600
C27—N8—C28	134.1 (3)	C1—N1—C2	116.9 (3)
C27—N8—H8N	110.5 (17)	C11—C16—C15	117.4 (3)
C28—N8—H8N	115.4 (17)	C11—C16—C17	121.2 (3)
C26—N6—N7	116.2 (3)	C15—C16—C17	121.4 (3)
C27—N7—N6	121.1 (3)	C4—C5—C8	122.0 (3)
C27—N7—H7N	119.5	C4—C5—H5A	119.0
N6—N7—H7N	119.5	C8—C5—H5A	119.0
C10—N3—N2	120.1 (3)	C5—C4—C3	121.2 (3)
C10—N3—H3N	120.0	C5—C4—H4B	119.4
N2—N3—H3N	120.0	C3—C4—H4B	119.4
C9—N2—N3	115.3 (3)	C30—C29—C28	120.2 (3)
N1—C3—C6	122.5 (3)	C30—C29—H29A	119.9
N1—C3—C4	121.1 (3)	C28—C29—H29A	119.9
C6—C3—C4	116.5 (3)	C13—C14—C15	119.9 (3)
N8—C27—N7	112.7 (3)	C13—C14—H14A	120.1
N8—C27—S2	129.1 (3)	C15—C14—H14A	120.1
N7—C27—S2	118.2 (2)	C31—C30—C29	119.6 (4)
C10—N4—C11	131.7 (3)	C31—C30—H30A	120.2
C10—N4—H4N	111 (2)	C29—C30—H30A	120.2
C11—N4—H4N	117 (2)	C14—C15—C16	121.9 (3)
N5—C20—C21	121.8 (3)	C14—C15—H15A	119.0
N5—C20—C23	121.2 (3)	C16—C15—H15A	119.0
C21—C20—C23	117.0 (3)	C31—C32—C33	121.6 (4)
C5—C8—C7	116.5 (3)	C31—C32—H32A	119.2
C5—C8—C9	123.9 (3)	C33—C32—H32A	119.2
C7—C8—C9	119.6 (3)	C30—C31—C32	120.4 (3)
C22—C25—C24	116.6 (3)	C30—C31—H31A	119.8
C22—C25—C26	123.6 (3)	C32—C31—H31A	119.8
C24—C25—C26	119.7 (3)	C14—C13—C12	119.5 (3)
C24—C23—C20	120.8 (3)	C14—C13—H13A	120.3
C24—C23—H23A	119.6	C12—C13—H13A	120.3
C20—C23—H23A	119.6	C11—C12—C13	121.2 (3)
C29—C28—C33	120.5 (3)	C11—C12—H12A	119.4
C29—C28—N8	123.2 (3)	C13—C12—H12A	119.4
C33—C28—N8	116.3 (3)	N1—C2—H2B	109.5
N3—C10—N4	113.9 (3)	N1—C2—H2C	109.5
N3—C10—S1	118.4 (2)	H2B—C2—H2C	109.5
N4—C10—S1	127.7 (2)	N1—C2—H2D	109.5
C22—C21—C20	121.4 (3)	H2B—C2—H2D	109.5
C22—C21—H21A	119.3	H2C—C2—H2D	109.5
C20—C21—H21A	119.3	C33—C34—H34A	109.5
C20—N5—C18	121.6 (3)	C33—C34—H34B	109.5
C20—N5—C19	121.7 (3)	H34A—C34—H34B	109.5
C18—N5—C19	116.7 (3)	C33—C34—H34C	109.5
C23—C24—C25	122.7 (3)	H34A—C34—H34C	109.5
C23—C24—H24A	118.7	H34B—C34—H34C	109.5
C25—C24—H24A	118.7	N5—C19—H19A	109.5
N2—C9—C8	122.8 (3)	N5—C19—H19B	109.5
N2—C9—H9A	116.4 (15)	H19A—C19—H19B	109.5
C8—C9—H9A	120.4 (15)	N5—C19—H19C	109.5
C6—C7—C8	122.3 (3)	H19A—C19—H19C	109.5
C6—C7—H7B	118.8	H19B—C19—H19C	109.5
C8—C7—H7B	118.8	C16—C17—H17A	109.5
N6—C26—C25	123.4 (3)	C16—C17—H17B	109.5
N6—C26—H26A	119.9 (19)	H17A—C17—H17B	109.5
C25—C26—H26A	116.6 (18)	C16—C17—H17C	109.5
C12—C11—C16	120.0 (3)	H17A—C17—H17C	109.5
C12—C11—N4	122.7 (3)	H17B—C17—H17C	109.5
C16—C11—N4	117.2 (3)	N5—C18—H18A	109.5
C21—C22—C25	121.5 (3)	N5—C18—H18B	109.5
C21—C22—H22A	119.2	H18A—C18—H18B	109.5
C25—C22—H22A	119.2	N5—C18—H18C	109.5
C32—C33—C28	117.8 (3)	H18A—C18—H18C	109.5
C32—C33—C34	120.3 (3)	H18B—C18—H18C	109.5
C28—C33—C34	121.9 (3)	N1—C1—H1A	109.5
C7—C6—C3	121.4 (3)	N1—C1—H1B	109.5
C7—C6—H6B	119.3	H1A—C1—H1B	109.5
C3—C6—H6B	119.3	N1—C1—H1C	109.5
C3—N1—C1	122.2 (3)	H1A—C1—H1C	109.5
C3—N1—C2	120.3 (3)	H1B—C1—H1C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4N···N2	0.95 (3)	2.05 (3)	2.587 (3)	114 (3)
C12—H12A···S1	0.93	2.64	3.239 (4)	123
C29—H29A···S2	0.93	2.57	3.257 (4)	131
N7—H7N···S1i	0.86	2.61	3.458 (3)	170
N3—H3N···S2ii	0.86	2.59	3.439 (3)	171
N8—H8N···N6	0.97 (3)	2.01 (3)	2.587 (4)	116 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4N⋯N2	0.95 (3)	2.05 (3)	2.587 (3)	114 (3)
C12—H12A⋯S1	0.93	2.64	3.239 (4)	123
C29—H29A⋯S2	0.93	2.57	3.257 (4)	131
N7—H7N⋯S1i	0.86	2.61	3.458 (3)	170
N3—H3N⋯S2ii	0.86	2.59	3.439 (3)	171
N8—H8N⋯N6	0.97 (3)	2.01 (3)	2.587 (4)	116 (2)

Symmetry codes: (i) ; (ii) .