2,9-Bis(1,3-benzothia-zol-2-yl)-1,10-phenanthroline dichloro-methane disolvate.

In the title compound, C(26)H(14)N(4)S(2)·2CH(2)Cl(2), the two pendant benzothia-zole groups are slightly twisted with respect to the phenanthroline core [dihedral angles = 1.03 (7) and 9.05 (5)°]. Weak inter-molecular C-H⋯N and C-H⋯Cl inter-actions occur in the crystal structure.

Related literature

For related literature, see: Kerbs (2003 ▶); Gude et al. (2005 ▶).

Experimental

Crystal data

C26H14N4S2·2CH2Cl2

M = 616.38

Triclinic,

a = 8.0969 (2) Å

b = 12.3990 (2) Å

c = 14.6006 (3) Å

α = 108.234 (1)°

β = 102.181 (1)°

γ = 94.335 (1)°

V = 1344.93 (5) Å3

Z = 2

Cu Kα radiation

μ = 5.67 mm−1

T = 100 (2) K

0.75 × 0.07 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.101, T max = 0.765

10764 measured reflections

4352 independent reflections

3831 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.079

S = 1.00

4352 reflections

415 parameters

All H-atom parameters refined

Δρmax = 0.37 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Bruker, 2005 ▶); software used to prepare material for publication: XCIF (Bruker, 2005 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019995/hb2737sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019995/hb2737Isup2.hkl

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

C26H14N4S2·2CH2Cl2	Z = 2
Mr = 616.38	F000 = 628
Triclinic, P1	Dx = 1.522 Mg m−3
Hall symbol: -P 1	Melting point > 573 K
a = 8.0969 (2) Å	Cu Kα radiation λ = 1.54178 Å
b = 12.3990 (2) Å	Cell parameters from 5710 reflections
c = 14.6006 (3) Å	θ = 3–65º
α = 108.234 (1)º	µ = 5.67 mm−1
β = 102.181 (1)º	T = 100 (2) K
γ = 94.335 (1)º	Needle, yellow
V = 1344.93 (5) Å3	0.75 × 0.07 × 0.05 mm

Bruker APEXII CCD diffractometer	4352 independent reflections
Radiation source: fine-focus sealed tube	3831 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.021
T = 100(2) K	θmax = 66.5º
ω scans	θmin = 3.3º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.101, Tmax = 0.765	k = −14→13
10764 measured reflections	l = 0→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031	All H-atom parameters refined
wR(F2) = 0.079	w = 1/[σ2(Fo2) + (0.0482P)2 + 0.6095P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
4352 reflections	Δρmax = 0.37 e Å−3
415 parameters	Δρmin = −0.38 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
S1	−0.16197 (6)	0.64055 (4)	0.22928 (3)	0.02003 (12)
S2	0.22351 (6)	0.40021 (4)	0.33879 (3)	0.01732 (12)
N1	−0.02010 (19)	0.73385 (13)	0.44545 (11)	0.0161 (3)
N2	0.17914 (18)	0.58715 (12)	0.50867 (11)	0.0155 (3)
N3	−0.2641 (2)	0.84086 (13)	0.26682 (12)	0.0211 (4)
N4	0.39069 (19)	0.33830 (12)	0.48236 (11)	0.0167 (3)
C1	−0.1189 (2)	0.80420 (15)	0.41677 (14)	0.0172 (4)
C2	−0.1611 (2)	0.90203 (16)	0.48337 (14)	0.0195 (4)
C3	−0.0951 (2)	0.92663 (16)	0.58255 (14)	0.0195 (4)
C4	0.0093 (2)	0.85441 (15)	0.61687 (13)	0.0164 (4)
C5	0.0753 (2)	0.87447 (16)	0.72043 (14)	0.0186 (4)
C6	0.1658 (2)	0.79970 (16)	0.75169 (14)	0.0196 (4)
C7	0.2011 (2)	0.69974 (15)	0.68113 (13)	0.0167 (4)
C8	0.2901 (2)	0.61883 (16)	0.71135 (14)	0.0188 (4)
C9	0.3234 (2)	0.52576 (16)	0.64199 (14)	0.0180 (4)
C10	0.2672 (2)	0.51431 (15)	0.54114 (14)	0.0160 (4)
C11	0.0425 (2)	0.75722 (15)	0.54414 (13)	0.0156 (4)
C12	0.1452 (2)	0.67863 (15)	0.57772 (13)	0.0159 (4)
C13	−0.1855 (2)	0.77490 (15)	0.30927 (14)	0.0174 (4)
C14	−0.2697 (2)	0.67676 (16)	0.12950 (14)	0.0198 (4)
C15	−0.3127 (2)	0.78754 (16)	0.16477 (14)	0.0202 (4)
C16	−0.3991 (3)	0.83493 (19)	0.09613 (15)	0.0274 (5)
C17	−0.4411 (3)	0.77107 (19)	−0.00363 (16)	0.0295 (5)
C18	−0.3985 (3)	0.66055 (19)	−0.03754 (16)	0.0280 (5)
C19	−0.3121 (3)	0.61241 (18)	0.02860 (15)	0.0247 (4)
C20	0.3034 (2)	0.41652 (15)	0.46417 (13)	0.0154 (4)
C21	0.3131 (2)	0.27520 (15)	0.30739 (14)	0.0177 (4)
C22	0.3991 (2)	0.25688 (15)	0.39417 (14)	0.0171 (4)
C23	0.4800 (2)	0.15927 (16)	0.38635 (15)	0.0196 (4)
C24	0.4739 (2)	0.08355 (16)	0.29330 (15)	0.0221 (4)
C25	0.3865 (3)	0.10262 (17)	0.20755 (15)	0.0245 (4)
C26	0.3058 (2)	0.19776 (17)	0.21311 (15)	0.0219 (4)
H2	−0.233 (3)	0.9445 (19)	0.4549 (16)	0.028 (6)*
H3	−0.118 (2)	0.9906 (18)	0.6279 (15)	0.017 (5)*
H5	0.054 (2)	0.9395 (18)	0.7645 (15)	0.016 (5)*
H6	0.207 (2)	0.8083 (16)	0.8204 (15)	0.015 (5)*
H8	0.328 (2)	0.6297 (17)	0.7835 (16)	0.021 (5)*
H9	0.380 (3)	0.4734 (18)	0.6609 (15)	0.022 (5)*
H16	−0.425 (3)	0.909 (2)	0.1181 (16)	0.029 (6)*
H17	−0.504 (3)	0.803 (2)	−0.0520 (17)	0.034 (6)*
H18	−0.429 (2)	0.6211 (17)	−0.1043 (16)	0.019 (5)*
H19	−0.286 (3)	0.535 (2)	0.0041 (16)	0.029 (6)*
H23	0.535 (3)	0.1458 (18)	0.4413 (16)	0.021 (5)*
H24	0.528 (3)	0.0190 (19)	0.2872 (15)	0.023 (5)*
H25	0.381 (3)	0.0496 (19)	0.1426 (16)	0.025 (6)*
H26	0.245 (3)	0.2090 (17)	0.1567 (16)	0.021 (5)*
Cl1S	0.32173 (7)	0.83312 (4)	0.34294 (4)	0.03355 (14)
Cl2S	0.32540 (7)	0.60371 (4)	0.20953 (4)	0.03418 (14)
C1S	0.3093 (3)	0.68551 (17)	0.33012 (15)	0.0217 (4)
H1SA	0.201 (3)	0.6616 (17)	0.3398 (14)	0.020 (5)*
H1SB	0.403 (3)	0.6741 (18)	0.3742 (16)	0.026 (6)*
Cl3S	0.07322 (8)	0.63525 (5)	0.93119 (5)	0.04547 (17)
Cl4S	0.05564 (10)	0.87470 (6)	1.03272 (6)	0.0674 (2)
C2S	0.1165 (3)	0.7470 (2)	1.04721 (19)	0.0406 (6)
H2SA	0.241 (4)	0.763 (2)	1.0784 (19)	0.049 (7)*
H2SB	0.047 (3)	0.726 (2)	1.087 (2)	0.049 (8)*

	U11	U22	U33	U12	U13	U23
S1	0.0242 (3)	0.0178 (2)	0.0193 (2)	0.00770 (18)	0.00485 (18)	0.00731 (19)
S2	0.0174 (2)	0.0169 (2)	0.0178 (2)	0.00438 (17)	0.00378 (17)	0.00611 (18)
N1	0.0145 (8)	0.0172 (8)	0.0189 (8)	0.0021 (6)	0.0067 (6)	0.0076 (6)
N2	0.0128 (8)	0.0152 (8)	0.0189 (8)	0.0011 (6)	0.0053 (6)	0.0058 (6)
N3	0.0232 (9)	0.0223 (9)	0.0222 (9)	0.0082 (7)	0.0080 (7)	0.0109 (7)
N4	0.0146 (8)	0.0159 (8)	0.0204 (8)	0.0020 (6)	0.0054 (6)	0.0066 (6)
C1	0.0142 (9)	0.0175 (9)	0.0226 (10)	0.0019 (7)	0.0076 (7)	0.0085 (8)
C2	0.0198 (10)	0.0174 (9)	0.0251 (10)	0.0062 (8)	0.0087 (8)	0.0097 (8)
C3	0.0205 (10)	0.0154 (10)	0.0241 (10)	0.0028 (8)	0.0100 (8)	0.0057 (8)
C4	0.0136 (9)	0.0153 (9)	0.0210 (10)	0.0000 (7)	0.0073 (7)	0.0055 (7)
C5	0.0174 (10)	0.0163 (10)	0.0206 (10)	0.0009 (7)	0.0079 (7)	0.0025 (8)
C6	0.0180 (10)	0.0232 (10)	0.0168 (10)	0.0010 (8)	0.0053 (7)	0.0054 (8)
C7	0.0124 (9)	0.0185 (9)	0.0185 (9)	−0.0010 (7)	0.0041 (7)	0.0059 (8)
C8	0.0144 (9)	0.0225 (10)	0.0203 (10)	0.0009 (7)	0.0045 (7)	0.0086 (8)
C9	0.0149 (10)	0.0186 (10)	0.0224 (10)	0.0038 (8)	0.0040 (7)	0.0098 (8)
C10	0.0104 (9)	0.0148 (9)	0.0233 (10)	0.0002 (7)	0.0054 (7)	0.0069 (8)
C11	0.0121 (9)	0.0162 (9)	0.0201 (10)	−0.0005 (7)	0.0060 (7)	0.0076 (7)
C12	0.0119 (9)	0.0155 (9)	0.0209 (10)	−0.0006 (7)	0.0063 (7)	0.0062 (8)
C13	0.0161 (10)	0.0169 (9)	0.0222 (10)	0.0032 (7)	0.0093 (7)	0.0078 (8)
C14	0.0163 (10)	0.0237 (10)	0.0228 (10)	0.0051 (8)	0.0065 (7)	0.0110 (8)
C15	0.0203 (10)	0.0228 (10)	0.0206 (10)	0.0065 (8)	0.0077 (7)	0.0089 (8)
C16	0.0330 (12)	0.0290 (12)	0.0264 (11)	0.0177 (9)	0.0105 (9)	0.0128 (9)
C17	0.0310 (12)	0.0381 (13)	0.0238 (11)	0.0151 (10)	0.0061 (9)	0.0145 (10)
C18	0.0301 (12)	0.0337 (12)	0.0187 (11)	0.0105 (9)	0.0040 (8)	0.0069 (9)
C19	0.0260 (11)	0.0233 (11)	0.0239 (11)	0.0069 (8)	0.0048 (8)	0.0068 (9)
C20	0.0109 (9)	0.0163 (9)	0.0199 (9)	−0.0003 (7)	0.0042 (7)	0.0077 (7)
C21	0.0136 (9)	0.0165 (9)	0.0235 (10)	0.0017 (7)	0.0053 (7)	0.0072 (8)
C22	0.0141 (9)	0.0163 (9)	0.0209 (10)	−0.0011 (7)	0.0057 (7)	0.0062 (8)
C23	0.0174 (10)	0.0185 (10)	0.0271 (11)	0.0030 (7)	0.0080 (8)	0.0116 (8)
C24	0.0206 (10)	0.0155 (10)	0.0323 (12)	0.0028 (8)	0.0115 (8)	0.0077 (8)
C25	0.0237 (11)	0.0199 (10)	0.0254 (11)	0.0005 (8)	0.0086 (8)	0.0005 (9)
C26	0.0182 (10)	0.0241 (10)	0.0201 (10)	0.0017 (8)	0.0027 (8)	0.0045 (8)
Cl1S	0.0412 (3)	0.0209 (3)	0.0436 (3)	0.0111 (2)	0.0151 (2)	0.0133 (2)
Cl2S	0.0537 (4)	0.0306 (3)	0.0227 (3)	0.0168 (2)	0.0146 (2)	0.0094 (2)
C1S	0.0249 (11)	0.0205 (10)	0.0228 (11)	0.0081 (8)	0.0076 (8)	0.0095 (8)
Cl3S	0.0506 (4)	0.0385 (3)	0.0509 (4)	0.0138 (3)	0.0195 (3)	0.0139 (3)
Cl4S	0.0650 (5)	0.0360 (4)	0.0686 (5)	0.0069 (3)	−0.0205 (4)	−0.0029 (3)
C2S	0.0348 (14)	0.0513 (15)	0.0376 (14)	0.0033 (11)	0.0082 (11)	0.0187 (12)

S1—C14	1.7370 (19)	C10—C20	1.469 (2)
S1—C13	1.7607 (18)	C11—C12	1.460 (2)
S2—C21	1.7334 (18)	C14—C19	1.391 (3)
S2—C20	1.7491 (18)	C14—C15	1.407 (3)
N1—C1	1.330 (2)	C15—C16	1.405 (3)
N1—C11	1.351 (2)	C16—C17	1.376 (3)
N2—C10	1.331 (2)	C16—H16	0.94 (2)
N2—C12	1.352 (2)	C17—C18	1.400 (3)
N3—C13	1.299 (2)	C17—H17	0.98 (2)
N3—C15	1.382 (2)	C18—C19	1.385 (3)
N4—C20	1.303 (2)	C18—H18	0.91 (2)
N4—C22	1.384 (2)	C19—H19	0.97 (2)
C1—C2	1.414 (3)	C21—C26	1.397 (3)
C1—C13	1.464 (3)	C21—C22	1.405 (3)
C2—C3	1.359 (3)	C22—C23	1.404 (3)
C2—H2	0.93 (2)	C23—C24	1.377 (3)
C3—C4	1.408 (3)	C23—H23	0.90 (2)
C3—H3	0.92 (2)	C24—C25	1.400 (3)
C4—C11	1.422 (3)	C24—H24	0.93 (2)
C4—C5	1.427 (3)	C25—C26	1.380 (3)
C5—C6	1.353 (3)	C25—H25	0.96 (2)
C5—H5	0.92 (2)	C26—H26	0.92 (2)
C6—C7	1.435 (3)	Cl1S—C1S	1.7733 (19)
C6—H6	0.96 (2)	Cl2S—C1S	1.773 (2)
C7—C8	1.405 (3)	C1S—H1SA	0.95 (2)
C7—C12	1.414 (3)	C1S—H1SB	0.94 (2)
C8—C9	1.364 (3)	Cl3S—C2S	1.766 (3)
C8—H8	0.99 (2)	Cl4S—C2S	1.754 (3)
C9—C10	1.404 (3)	C2S—H2SA	0.99 (3)
C9—H9	0.90 (2)	C2S—H2SB	0.97 (3)
C14—S1—C13	88.49 (9)	N3—C15—C16	125.46 (18)
C21—S2—C20	88.48 (9)	N3—C15—C14	115.44 (17)
C1—N1—C11	117.85 (15)	C16—C15—C14	119.10 (18)
C10—N2—C12	117.47 (15)	C17—C16—C15	119.06 (19)
C13—N3—C15	110.46 (16)	C17—C16—H16	120.7 (14)
C20—N4—C22	110.30 (15)	C15—C16—H16	120.3 (14)
N1—C1—C2	123.86 (17)	C16—C17—C18	121.17 (19)
N1—C1—C13	116.02 (16)	C16—C17—H17	119.5 (13)
C2—C1—C13	120.12 (16)	C18—C17—H17	119.3 (13)
C3—C2—C1	118.15 (18)	C19—C18—C17	120.83 (19)
C3—C2—H2	125.4 (14)	C19—C18—H18	120.8 (13)
C1—C2—H2	116.4 (14)	C17—C18—H18	118.4 (13)
C2—C3—C4	120.23 (18)	C18—C19—C14	118.09 (19)
C2—C3—H3	120.3 (12)	C18—C19—H19	119.8 (13)
C4—C3—H3	119.5 (12)	C14—C19—H19	122.1 (13)
C3—C4—C11	117.41 (17)	N4—C20—C10	124.42 (16)
C3—C4—C5	122.00 (17)	N4—C20—S2	116.40 (14)
C11—C4—C5	120.56 (17)	C10—C20—S2	119.17 (13)
C6—C5—C4	120.92 (17)	C26—C21—C22	121.22 (17)
C6—C5—H5	121.6 (12)	C26—C21—S2	128.96 (15)
C4—C5—H5	117.4 (12)	C22—C21—S2	109.82 (14)
C5—C6—C7	120.55 (17)	N4—C22—C23	125.39 (17)
C5—C6—H6	123.3 (12)	N4—C22—C21	114.98 (16)
C7—C6—H6	116.1 (12)	C23—C22—C21	119.60 (17)
C8—C7—C12	117.46 (16)	C24—C23—C22	119.06 (19)
C8—C7—C6	121.80 (17)	C24—C23—H23	120.1 (13)
C12—C7—C6	120.73 (16)	C22—C23—H23	120.9 (13)
C9—C8—C7	120.03 (17)	C23—C24—C25	120.61 (18)
C9—C8—H8	120.5 (12)	C23—C24—H24	119.8 (13)
C7—C8—H8	119.5 (12)	C25—C24—H24	119.6 (13)
C8—C9—C10	118.20 (17)	C26—C25—C24	121.51 (19)
C8—C9—H9	120.5 (13)	C26—C25—H25	117.7 (13)
C10—C9—H9	121.3 (13)	C24—C25—H25	120.8 (13)
N2—C10—C9	124.03 (17)	C25—C26—C21	117.99 (19)
N2—C10—C20	116.04 (16)	C25—C26—H26	121.5 (13)
C9—C10—C20	119.93 (16)	C21—C26—H26	120.4 (13)
N1—C11—C4	122.47 (16)	Cl2S—C1S—Cl1S	110.15 (11)
N1—C11—C12	118.95 (16)	Cl2S—C1S—H1SA	109.8 (12)
C4—C11—C12	118.57 (16)	Cl1S—C1S—H1SA	107.6 (12)
N2—C12—C7	122.76 (16)	Cl2S—C1S—H1SB	105.3 (13)
N2—C12—C11	118.65 (16)	Cl1S—C1S—H1SB	110.1 (13)
C7—C12—C11	118.56 (16)	H1SA—C1S—H1SB	113.8 (18)
N3—C13—C1	124.79 (16)	Cl4S—C2S—Cl3S	111.12 (14)
N3—C13—S1	116.14 (14)	Cl4S—C2S—H2SA	106.9 (15)
C1—C13—S1	119.06 (13)	Cl3S—C2S—H2SA	109.9 (15)
C19—C14—C15	121.75 (18)	Cl4S—C2S—H2SB	106.1 (16)
C19—C14—S1	128.78 (15)	Cl3S—C2S—H2SB	108.2 (16)
C15—C14—S1	109.46 (14)	H2SA—C2S—H2SB	115 (2)
C11—N1—C1—C2	0.4 (3)	C14—S1—C13—N3	−0.46 (15)
C11—N1—C1—C13	−179.31 (15)	C14—S1—C13—C1	178.90 (14)
N1—C1—C2—C3	0.9 (3)	C13—S1—C14—C19	−179.45 (19)
C13—C1—C2—C3	−179.40 (16)	C13—S1—C14—C15	0.63 (14)
C1—C2—C3—C4	−1.3 (3)	C13—N3—C15—C16	−179.48 (19)
C2—C3—C4—C11	0.5 (3)	C13—N3—C15—C14	0.4 (2)
C2—C3—C4—C5	−177.33 (17)	C19—C14—C15—N3	179.34 (17)
C3—C4—C5—C6	175.55 (18)	S1—C14—C15—N3	−0.7 (2)
C11—C4—C5—C6	−2.2 (3)	C19—C14—C15—C16	−0.8 (3)
C4—C5—C6—C7	1.5 (3)	S1—C14—C15—C16	179.16 (15)
C5—C6—C7—C8	−177.99 (17)	N3—C15—C16—C17	−179.27 (19)
C5—C6—C7—C12	1.3 (3)	C14—C15—C16—C17	0.8 (3)
C12—C7—C8—C9	1.7 (3)	C15—C16—C17—C18	−0.4 (3)
C6—C7—C8—C9	−179.01 (17)	C16—C17—C18—C19	−0.2 (3)
C7—C8—C9—C10	0.3 (3)	C17—C18—C19—C14	0.3 (3)
C12—N2—C10—C9	1.2 (2)	C15—C14—C19—C18	0.2 (3)
C12—N2—C10—C20	−179.38 (15)	S1—C14—C19—C18	−179.70 (16)
C8—C9—C10—N2	−1.8 (3)	C22—N4—C20—C10	178.79 (16)
C8—C9—C10—C20	178.81 (16)	C22—N4—C20—S2	−0.35 (19)
C1—N1—C11—C4	−1.3 (2)	N2—C10—C20—N4	178.51 (16)
C1—N1—C11—C12	177.38 (16)	C9—C10—C20—N4	−2.1 (3)
C3—C4—C11—N1	0.9 (3)	N2—C10—C20—S2	−2.4 (2)
C5—C4—C11—N1	178.72 (16)	C9—C10—C20—S2	177.03 (13)
C3—C4—C11—C12	−177.81 (16)	C21—S2—C20—N4	0.89 (14)
C5—C4—C11—C12	0.0 (2)	C21—S2—C20—C10	−178.30 (14)
C10—N2—C12—C7	0.9 (2)	C20—S2—C21—C26	177.75 (18)
C10—N2—C12—C11	−177.37 (15)	C20—S2—C21—C22	−1.12 (13)
C8—C7—C12—N2	−2.3 (3)	C20—N4—C22—C23	−178.48 (17)
C6—C7—C12—N2	178.33 (16)	C20—N4—C22—C21	−0.6 (2)
C8—C7—C12—C11	175.94 (16)	C26—C21—C22—N4	−177.75 (16)
C6—C7—C12—C11	−3.4 (2)	S2—C21—C22—N4	1.22 (19)
N1—C11—C12—N2	2.3 (2)	C26—C21—C22—C23	0.3 (3)
C4—C11—C12—N2	−178.98 (15)	S2—C21—C22—C23	179.26 (14)
N1—C11—C12—C7	−176.04 (15)	N4—C22—C23—C24	178.07 (17)
C4—C11—C12—C7	2.7 (2)	C21—C22—C23—C24	0.3 (3)
C15—N3—C13—C1	−179.20 (16)	C22—C23—C24—C25	−0.8 (3)
C15—N3—C13—S1	0.1 (2)	C23—C24—C25—C26	0.8 (3)
N1—C1—C13—N3	−170.20 (17)	C24—C25—C26—C21	−0.2 (3)
C2—C1—C13—N3	10.1 (3)	C22—C21—C26—C25	−0.3 (3)
N1—C1—C13—S1	10.5 (2)	S2—C21—C26—C25	−179.07 (15)
C2—C1—C13—S1	−169.22 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C1S—H1SB···N4i	0.94 (2)	2.44 (2)	3.360 (3)	166.7 (19)
C3—H3···Cl1Sii	0.92 (2)	2.82 (2)	3.615 (2)	145.6 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1S—H1SB⋯N4i	0.94 (2)	2.44 (2)	3.360 (3)	166.7 (19)
C3—H3⋯Cl1Sii	0.92 (2)	2.82 (2)	3.615 (2)	145.6 (16)

Symmetry codes: (i) ; (ii) .