2,9-Bis(1,3-benzothia­zol-2-yl)-1,10-phenanthroline dichloro­methane disolvate

Akther, J.; Lindeman, S.; Karim, M.R.

doi:10.1107/S1600536808019995

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1836

doi:10.1107/S1600536808019995

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2,9-Bis(1,3-benzothiazol-2-yl)-1,10-phenanthroline dichloromethane disolvate

Jesmin Akther,^a ‡ Sergey Lindeman ^b and Mohammad Rezaul Karim ^a ^*

^aTennessee State University, Department of Chemistry, 3500 John A Merritt Boulevard, Nashville, TN 37209, USA, and ^bDepartment of Chemistry, Marquette University, PO Box 1881, Milwaukee, WI 53201-1881, USA
^*Correspondence e-mail: mkarim@tnstate.edu

(Received 25 May 2008; accepted 30 June 2008; online 30 August 2008)

In the title compound, C₂₆H₁₄N₄S₂·2CH₂Cl₂, the two pendant benzothiazole groups are slightly twisted with respect to the phenanthroline core [dihedral angles = 1.03 (7) and 9.05 (5)°]. Weak intermolecular C—H⋯N and C—H⋯Cl interactions occur in the crystal structure.

Related literature

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

Experimental

Crystal data

C₂₆H₁₄N₄S₂·2CH₂Cl₂
M_r = 616.38
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.031
wR(F²) = 0.079
S = 1.00
4352 reflections
415 parameters
All H-atom parameters refined
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.38 e Å⁻³

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) -x+1, -y+1, -z+1; (ii) -x, -y+2, -z+1.

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).

Supporting information

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

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

checkCIF report

Comment top

As part of our studies of the biological properties of Schiff bases, we attempted to synthesize Schiff bases from 1,10-phenanthroline. It has been found in the literature that Schiff bases formed from S-alkyl and S-aryl substituted amines contain both hard nitrogen and soft sulfur donor atoms. (e.g. Kerbs, 2003). Consequently, these compounds are capable of forming stable complexes with a wide variety of metal ions. These complexes have interesting physio-chemical properties and potential chemotherapeutic effets (e.g. Gude et al.2005). In this paper the synthesis and structure of the title compound, (I), are reported.

The main molecule is close to planar, with dihedral angles of 9.05 (5)° and 1.03 (7)° for the S1 and S2 benzothiazolyl moieties respectively, with respect to the phenanthroline core. There are two dichloromethane solvent molecules in the asymmetric unit (Fig. 1).

Weak intermolecular C—H···N and C—H···Cl interactions (Table 1) may help to stabilise the packing.

Related literature top

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

Experimental top

To a solution of 1,10-phenanthroline (50 mg, 0.20 mmol) in 5 ml CHCl₃, 2-mercaptoaniline (0.60 µL, 0.40 mmol) was added followed by the addition of p-toluene sulfonic acid mono hydrate (76 mg, 0.40 mmol) in a Pyrex tube under argon. The tube was placed in a CEM microwave. The reaction conditions were set up as follows: power: 300 W, ramp time: 20 min, hold time: 20 min, and temperature: 373 K. When the reaction vessel was opened, a yellow precipitate was observed, which was filtered off and washed with cold CHCl₃ and dried under vacuum. [y: 30 mg, 40%]. IR: ν= 1597 cm-1 (C=N), 1550 cm-1 (C=C). 1H-NMR([D₃],CDCl₃, 300 MHz): δ=8.74 (d, ⁴J= 9.0 Hz,, 8-H, 3-H), 8.41 (d, ³J=9.0 Hz,2H, H-4, H-7), 7.88 (s, 2H, H-5, and H-6), 8.169 (t, ⁴H, 2 J= 8.1 Hz, ¹J=8.7 Hz,H-16, H-16', H-13, H-13'), 7.53 (m, 4H, H-14, H-14', H-15, H-15').13 C: NMR([D₃], CDCl₃, 75.5 MHz): δ= 155 (C-2, C-9), δ= 146 (C-11,C-12), δ=137.48 (C-3, C-8). δ=127.591 (C-4, C-7,), δ=126.60 (C-5, C-6), δ= 172 (C-13, C-13'), δ= 152 (C-14, C-14'), δ= 130.26 (C-15, C-15'), δ=137.0 (C-19, C-19') δ=126.18 (C-19, C-19'). δ=124.04 (C-18, C-18'). δ=122.54 (C-17, C-17'). δ=120.51 (C-16, C-16').

Yellow needles of (I) were grown from CH₂Cl₂/hexane at 253 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

Figures top

	Fig. 1. The molecular structure of (I) showing 50% displacement ellipsoids for the non-hydrogen atoms.
	Fig. 2. The formation of the title compound.

2,9-Bis(1,3-benzothiazol-2-yl)-1,10-phenanthroline dichloromethane disolvate top

Crystal data top

C₂₆H₁₄N₄S₂·2CH₂Cl₂	Z = 2
M_r = 616.38	F(000) = 628
Triclinic, P1	D_x = 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 = 3–65°
α = 108.234 (1)°	µ = 5.67 mm⁻¹
β = 102.181 (1)°	T = 100 K
γ = 94.335 (1)°	Needle, yellow
V = 1344.93 (5) Å³	0.75 × 0.07 × 0.05 mm

Data collection top

Bruker APEXII CCD diffractometer	4352 independent reflections
Radiation source: fine-focus sealed tube	3831 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 66.5°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
T_min = 0.101, T_max = 0.765	k = −14→13
10764 measured reflections	l = 0→17

Refinement top

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)] = 0.031	Hydrogen site location: difference Fourier map
wR(F²) = 0.079	All H-atom parameters refined
S = 1.00	w = 1/[σ²(F_o²) + (0.0482P)² + 0.6095P] where P = (F_o² + 2F_c²)/3
4352 reflections	(Δ/σ)_max = 0.001
415 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₂₆H₁₄N₄S₂·2CH₂Cl₂	γ = 94.335 (1)°
M_r = 616.38	V = 1344.93 (5) Å³
Triclinic, P1	Z = 2
a = 8.0969 (2) Å	Cu Kα radiation
b = 12.3990 (2) Å	µ = 5.67 mm⁻¹
c = 14.6006 (3) Å	T = 100 K
α = 108.234 (1)°	0.75 × 0.07 × 0.05 mm
β = 102.181 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4352 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3831 reflections with I > 2σ(I)
T_min = 0.101, T_max = 0.765	R_int = 0.021
10764 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.079	All H-atom parameters refined
S = 1.00	Δρ_max = 0.37 e Å⁻³
4352 reflections	Δρ_min = −0.38 e Å⁻³
415 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1; (ii) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₆H₁₄N₄S₂·2CH₂Cl₂
M_r	616.38
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.0969 (2), 12.3990 (2), 14.6006 (3)
α, β, γ (°)	108.234 (1), 102.181 (1), 94.335 (1)
V (Å³)	1344.93 (5)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	5.67
Crystal size (mm)	0.75 × 0.07 × 0.05

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.101, 0.765
No. of measured, independent and observed [I > 2σ(I)] reflections	10764, 4352, 3831
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.079, 1.00
No. of reflections	4352
No. of parameters	415
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.38

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Bruker, 2005), XCIF (Bruker, 2005).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1; (ii) −x, −y+2, −z+1.

Footnotes

‡Current address: Department of Chemistry and Biochemistry, 3210 N Cramer Street, Milwaukee, WI 53211, USA.

References

Bruker (2005). APEX2, SAINT, SADABS, XP and XCIF. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gude, L., Fernandez, M. J., Grant, K. B. & Loernte, A. (2005). Org. Biomol. Chem. 3, 1856–1862. Web of Science CrossRef PubMed CAS Google Scholar
Kerbs, F. C. (2003). Tetrahedron Lett. 44, 6643–6646. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 9| September 2008| Page o1836

doi:10.1107/S1600536808019995

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,9-Bis(1,3-benzo­thia­zol-2-yl)-1,10-phenanthroline di­chloro­methane disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

References

organic compounds

2,9-Bis(1,3-benzothiazol-2-yl)-1,10-phenanthroline dichloromethane disolvate