The molecular structure of the title compound, C
18H
16N
2S
4, has a center of symmetry. All the C and S atoms in the central alkyl chain are coplanar, and this plane is almost perpendicular to the benzothiazolyl rings. The molecules are linked together by intermolecular S
S interactions to form a one-dimensional chain.
Supporting information
CCDC reference: 209945
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.042
- wR factor = 0.081
- Data-to-parameter ratio = 14.3
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
ABSTM_02 Alert C The ratio of Tmax/Tmin expected RT(exp) is > 1.10
Absorption corrections should be applied.
Tmin and Tmax expected: 0.877 0.969
RT(exp) = 1.105
REFLT_03
From the CIF: _diffrn_reflns_theta_max 28.29
From the CIF: _reflns_number_total 2020
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 2163
Completeness (_total/calc) 93.39%
Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
The title compound, (I), was prepared from 2-mercaptobenzothiazole and 1,4-dibromobutane in 56% yield, using the similar reaction reported by Chen et al. (2003). Crystals of (I) suitable for X-ray analysis were grown from a chloroform solution. Calculated (%) for C18H16N2S4: C 55.64, H 4.15, N 7.21; found (%): C 55.48, H 4.10, N 7.18.
All H atoms were located from difference syntheses and refined isotropically. The C—H distances are in the range 0.89 (2)–0.98 (2) Å.
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
Crystal data top
C18H16N2S4 | F(000) = 404 |
Mr = 388.57 | Dx = 1.49 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.9072 (18) Å | Cell parameters from 887 reflections |
b = 4.9003 (8) Å | θ = 5.5–46.2° |
c = 16.767 (3) Å | µ = 0.55 mm−1 |
β = 104.868 (3)° | T = 293 K |
V = 866.2 (2) Å3 | Block, colourless |
Z = 2 | 0.25 × 0.20 × 0.06 mm |
Data collection top
Bruker SMART diffractometer | Rint = 0.050 |
ϕ and ω scans | θmax = 28.3°, θmin = 1.9° |
5025 measured reflections | h = −14→14 |
2020 independent reflections | k = −6→6 |
1248 reflections with I > 2σ(I) | l = −17→22 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.0257P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.081 | (Δ/σ)max = 0.001 |
S = 0.84 | Δρmax = 0.34 e Å−3 |
2020 reflections | Δρmin = −0.25 e Å−3 |
141 parameters | |
Crystal data top
C18H16N2S4 | V = 866.2 (2) Å3 |
Mr = 388.57 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.9072 (18) Å | µ = 0.55 mm−1 |
b = 4.9003 (8) Å | T = 293 K |
c = 16.767 (3) Å | 0.25 × 0.20 × 0.06 mm |
β = 104.868 (3)° | |
Data collection top
Bruker SMART diffractometer | 1248 reflections with I > 2σ(I) |
5025 measured reflections | Rint = 0.050 |
2020 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.081 | All H-atom parameters refined |
S = 0.84 | Δρmax = 0.34 e Å−3 |
2020 reflections | Δρmin = −0.25 e Å−3 |
141 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.18452 (6) | 0.44087 (13) | 0.50542 (4) | 0.0512 (2) | |
S2 | 0.06435 (6) | 0.06905 (13) | 0.60430 (4) | 0.0454 (2) | |
N | 0.30799 (18) | 0.1533 (3) | 0.64017 (11) | 0.0377 (5) | |
C2 | 0.3415 (3) | 0.5880 (5) | 0.52488 (19) | 0.0483 (7) | |
C1 | 0.4362 (2) | 0.4279 (5) | 0.49193 (18) | 0.0422 (6) | |
C3 | 0.2027 (2) | 0.2190 (4) | 0.58924 (14) | 0.0371 (6) | |
C4 | 0.2856 (2) | −0.0360 (4) | 0.69731 (14) | 0.0343 (5) | |
C5 | 0.3778 (3) | −0.1570 (5) | 0.75961 (15) | 0.0425 (6) | |
C6 | 0.3417 (3) | −0.3499 (5) | 0.80885 (16) | 0.0486 (7) | |
C7 | 0.2159 (3) | −0.4198 (5) | 0.79782 (17) | 0.0510 (7) | |
C8 | 0.1227 (3) | −0.3018 (5) | 0.73710 (16) | 0.0462 (7) | |
C9 | 0.1582 (2) | −0.1086 (4) | 0.68654 (13) | 0.0351 (5) | |
H1 | 0.462 (2) | −0.111 (4) | 0.7654 (13) | 0.043 (7)* | |
H2 | 0.405 (2) | −0.434 (4) | 0.8495 (14) | 0.047 (7)* | |
H3 | 0.198 (2) | −0.546 (4) | 0.8316 (14) | 0.050 (7)* | |
H4 | 0.0397 (19) | −0.353 (4) | 0.7272 (12) | 0.033 (6)* | |
H5 | 0.374 (2) | 0.621 (4) | 0.5844 (14) | 0.052 (7)* | |
H6 | 0.325 (2) | 0.756 (5) | 0.4976 (14) | 0.062 (8)* | |
H7 | 0.4468 (18) | 0.250 (4) | 0.5191 (12) | 0.038 (6)* | |
H8 | 0.402 (2) | 0.398 (4) | 0.4328 (14) | 0.042 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0495 (4) | 0.0549 (4) | 0.0510 (4) | 0.0046 (3) | 0.0164 (3) | 0.0151 (4) |
S2 | 0.0337 (4) | 0.0553 (4) | 0.0472 (4) | −0.0005 (3) | 0.0105 (3) | 0.0071 (3) |
N | 0.0353 (12) | 0.0392 (11) | 0.0401 (12) | −0.0015 (9) | 0.0121 (10) | 0.0001 (10) |
C2 | 0.0632 (19) | 0.0383 (15) | 0.0494 (18) | −0.0044 (14) | 0.0256 (15) | −0.0014 (15) |
C1 | 0.0548 (18) | 0.0344 (14) | 0.0427 (16) | −0.0051 (12) | 0.0217 (14) | −0.0024 (13) |
C3 | 0.0397 (15) | 0.0367 (13) | 0.0379 (13) | 0.0015 (11) | 0.0155 (12) | −0.0012 (11) |
C4 | 0.0367 (14) | 0.0330 (12) | 0.0347 (13) | −0.0002 (11) | 0.0117 (11) | −0.0049 (11) |
C5 | 0.0360 (16) | 0.0464 (15) | 0.0441 (15) | 0.0017 (13) | 0.0082 (13) | 0.0007 (13) |
C6 | 0.0513 (19) | 0.0510 (16) | 0.0414 (16) | 0.0081 (14) | 0.0079 (14) | 0.0051 (14) |
C7 | 0.062 (2) | 0.0468 (16) | 0.0496 (17) | 0.0026 (15) | 0.0244 (16) | 0.0107 (14) |
C8 | 0.0401 (17) | 0.0488 (16) | 0.0538 (17) | −0.0035 (14) | 0.0197 (15) | 0.0048 (14) |
C9 | 0.0343 (14) | 0.0377 (13) | 0.0353 (13) | 0.0001 (11) | 0.0125 (11) | −0.0021 (11) |
Geometric parameters (Å, º) top
S1—C3 | 1.747 (2) | C1—H8 | 0.98 (2) |
S1—C2 | 1.809 (3) | C4—C5 | 1.384 (3) |
S2—C9 | 1.727 (2) | C4—C9 | 1.399 (3) |
S2—C3 | 1.754 (2) | C5—C6 | 1.377 (3) |
N—C3 | 1.284 (3) | C5—H1 | 0.93 (2) |
N—C4 | 1.400 (3) | C6—C7 | 1.380 (4) |
C2—C1 | 1.510 (3) | C6—H2 | 0.93 (2) |
C2—H5 | 0.98 (2) | C7—C8 | 1.369 (3) |
C2—H6 | 0.94 (2) | C7—H3 | 0.89 (2) |
C1—C1i | 1.522 (5) | C8—C9 | 1.390 (3) |
C1—H7 | 0.976 (19) | C8—H4 | 0.913 (19) |
| | | |
C3—S1—C2 | 101.31 (13) | C5—C4—C9 | 119.6 (2) |
C9—S2—C3 | 88.30 (11) | C5—C4—N | 125.4 (2) |
C3—N—C4 | 109.75 (19) | C9—C4—N | 115.0 (2) |
C1—C2—S1 | 115.56 (18) | C6—C5—C4 | 118.8 (2) |
C1—C2—H5 | 110.8 (13) | C6—C5—H1 | 122.2 (13) |
S1—C2—H5 | 109.1 (13) | C4—C5—H1 | 119.0 (13) |
C1—C2—H6 | 109.9 (13) | C5—C6—C7 | 121.2 (3) |
S1—C2—H6 | 102.0 (15) | C5—C6—H2 | 117.9 (14) |
H5—C2—H6 | 109.0 (19) | C7—C6—H2 | 120.9 (14) |
C2—C1—C1i | 111.9 (2) | C8—C7—C6 | 121.2 (3) |
C2—C1—H7 | 107.6 (11) | C8—C7—H3 | 121.6 (16) |
C1i—C1—H7 | 109.8 (12) | C6—C7—H3 | 117.2 (16) |
C2—C1—H8 | 109.4 (13) | C7—C8—C9 | 118.1 (2) |
C1i—C1—H8 | 109.9 (12) | C7—C8—H4 | 122.2 (13) |
H7—C1—H8 | 108.1 (17) | C9—C8—H4 | 119.6 (13) |
N—C3—S1 | 126.06 (18) | C8—C9—C4 | 121.1 (2) |
N—C3—S2 | 117.06 (17) | C8—C9—S2 | 129.0 (2) |
S1—C3—S2 | 116.88 (14) | C4—C9—S2 | 109.90 (16) |
| | | |
C3—S1—C2—C1 | 86.1 (2) | C4—C5—C6—C7 | −1.1 (4) |
S1—C2—C1—C1i | 177.7 (3) | C5—C6—C7—C8 | 0.6 (4) |
C4—N—C3—S1 | −177.95 (15) | C6—C7—C8—C9 | 0.0 (4) |
C4—N—C3—S2 | 1.2 (2) | C7—C8—C9—C4 | −0.1 (3) |
C2—S1—C3—N | −10.6 (2) | C7—C8—C9—S2 | 178.60 (19) |
C2—S1—C3—S2 | 170.25 (13) | C5—C4—C9—C8 | −0.4 (3) |
C9—S2—C3—N | −1.60 (18) | N—C4—C9—C8 | 177.75 (19) |
C9—S2—C3—S1 | 177.61 (13) | C5—C4—C9—S2 | −179.31 (17) |
C3—N—C4—C5 | 178.0 (2) | N—C4—C9—S2 | −1.2 (2) |
C3—N—C4—C9 | 0.0 (3) | C3—S2—C9—C8 | −177.4 (2) |
C9—C4—C5—C6 | 1.0 (3) | C3—S2—C9—C4 | 1.45 (16) |
N—C4—C5—C6 | −177.0 (2) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data |
Chemical formula | C18H16N2S4 |
Mr | 388.57 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 10.9072 (18), 4.9003 (8), 16.767 (3) |
β (°) | 104.868 (3) |
V (Å3) | 866.2 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.55 |
Crystal size (mm) | 0.25 × 0.20 × 0.06 |
|
Data collection |
Diffractometer | Bruker SMART diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5025, 2020, 1248 |
Rint | 0.050 |
(sin θ/λ)max (Å−1) | 0.667 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.081, 0.84 |
No. of reflections | 2020 |
No. of parameters | 141 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.34, −0.25 |
Selected bond lengths (Å) topS1—C3 | 1.747 (2) | S2—C3 | 1.754 (2) |
S1—C2 | 1.809 (3) | C2—C1 | 1.510 (3) |
S2—C9 | 1.727 (2) | C1—C1i | 1.522 (5) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
One of reasons for the recent intensive interest in design flexible multidentate ligand is to develop a new family of microporous, helicate materials, and other coordination polymers with unusual porous structures (Cai et al., 2001; Albada et al., 2000; Zhang et al., 2002). Moreover, the flexiblity and conformational freedom of such ligands offer the possibility of generating unique frameworks with useful properties (Bu et al., 2001; Hou et al., 2002). As part of our systematic investigation of the coordination chemistry of flexible ligand, we report here the synthesis and crystal structure of the title compound, (I).
The title molecule has a center of symmetry at the mid-point of the central C—C bond (Fig. 1). The C1—C2 and C1—C1i bond lengths are all close to the standard value for a single-bond length (see Table 1). All the C and S atoms between the two benzothiazolyl rings are coplanar; this plane is almost perpendicular to the planes of the benzothiazolyl rings, which are parallel to each other. The S—C bond distances are in the range 1.727 (2)–1.809 (3) Å, which are similar to those of S—C bonds of the analogous compound 1,5-bis(benzothiazolyl)-3-thiapentane (Grapperhaus et al., 2002), the C atom in the longest C—S bond belonging to the methylene group. The molecules are linked together by an intermolecular S2···S2(-x, −y, 1 − z) interaction of 3.485 (2) Å to form a one-dimensional chain.