Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041347/pv2025sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041347/pv2025Isup2.hkl |
CCDC reference: 660361
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.056
- wR factor = 0.129
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT391_ALERT_3_B Deviating Methyl C12 H-C-H Bond Angle ...... 99.00 Deg. PLAT735_ALERT_1_B D-H Calc 1.05(4), Rep 1.045(5) ...... 8.00 su-Ra C14 -H14 1.555 1.555 PLAT736_ALERT_1_B H...A Calc 2.68(4), Rep 2.685(6) ...... 6.67 su-Ra H14 -N1 1.555 3.775
Alert level C PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.33 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S2 PLAT245_ALERT_2_C U(iso) H22B Smaller than U(eq) C22 by ... 0.01 AngSq PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT350_ALERT_3_C Short C-H Bond (0.96A) C12 - H12B ... 0.82 Ang. PLAT350_ALERT_3_C Short C-H Bond (0.96A) C22 - H22B ... 0.83 Ang. PLAT351_ALERT_3_C Long C-H Bond (0.96A) C22 - H22A ... 1.16 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C4 - C21 ... 1.44 Ang. PLAT390_ALERT_3_C Deviating Methyl C22 X-C-H Bond Angle ...... 117.00 Deg. PLAT390_ALERT_3_C Deviating Methyl C22 X-C-H Bond Angle ...... 102.00 Deg. PLAT391_ALERT_3_C Deviating Methyl C12 H-C-H Bond Angle ...... 119.00 Deg. PLAT480_ALERT_4_C Long H...A H-Bond Reported H14 .. N1 .. 2.68 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 9 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
To a suspension of NaH (60%, 0.88 g, 22 mmol) in dry benzene (20 ml) and dry DMF (20 ml) under stirring, a solution of (2-phenyl-1,3-thiazol-4-yl)- acetonitrile (2 g, 10 mmol) in dry benzene (10 ml) was added at 281 K over a period of 15 min and further stirred at 273–361 K for 15 min. Solution of a-oxoketene dithioacetal (10 mmol) in dry DMF (10 ml) was added slowly over 10 min to this mixture with stirring at 273–361 K. The reaction mixture was stirred at room temperature for 4–5 h. The solution was poured into an aqueous ammonium chloride solution (8%, 200 ml), and extracted with benzene (50 ml × 2). The collective extract was washed with water (100 ml × 3), dried over anhydrous sodium sulfate, passed through a silica bed, and concentrated. After standing for 2 h, the crystallized material was separated by filtration and washed with a mixture of benzene and hexane (1:1) to afford a colorless solid, 5-(4-methylphenyl)-3-(methylthio)-5-oxo- 2-(2-phenyl-1,3-thiazol-4-yl)pent-2-enenitrile.
The solution of 5-(4-Methylphenyl)-3-(methylthio)-5-oxo- 2-(2-phenyl-1,3-thiazol-4-yl)pent-2-enenitrile(2.5 mmol) and p-toluene sulphonic acid (1 g, 5.3 mmol) in benzene was refluxed for 4–6 h. The reaction mixture (monitored by TLC) was concentrated, dissolved in chloroform, and poured into aqueous sodium bicarbonate solution (6%, 150 ml). The organic layer was separated, washed with water (100 ml × 3), and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to yield the greenish yellow oil, which was purified by column chromatography using a benzene-hexane mixture (45:55v/v-80:20v/v) as eluent to furnish a yellow or greenish yellow solid 7-(4-methylphenyl)- 5-(methylthio)-2-phenyl-1,3-benzothiazole-4-carbonitrile (Hedge et al., 2006). Good quality single-crystals of (I) were grown from a chloroform solution by slow evaporation at room temperature.
Benzothiazoles are bicyclic ring systems with multiple applications. They comprise a novel class of therapeutic compounds shown to exert a wide range of biological activities. Substituted derivatives of benzothiazole demonstrate several interesting pharmacological functions due to their potent capacity to interfere with cellular structures. For instance, the phenyl-substituted benzothiazoles show antitumor activity (Bradshaw, Bibby et al., 2002; Bradshaw, Chua et al., 2002; Hutchinson et al., 2002). They also act as antimicrobial (Holbová et al., 1990; Brownlee et al., 1992) and antimycobacterial (Sidóová & Odlerová, 1990) agents. In adition, they are used in the preparation of dyes (Brooker et al., 1940), organic synthesis of thermostable polymers (Corey & Boger, 1978) and as herbicides which inhibit photosynthesis (Králová et al., 1992). In this paper, we report the structure of the title compound, (I), which has been synthesized in our laboratory.
In (I), the benzothiazole and methylphenyl rings are inclined at an angle of 31.23 (8)° to each other (Fig. 1). The 2-subtituted phenyl ring is inclined with respect to benzothiazole ring at an angle of 7.74 (10)°. The methylthio and carbonitrile groups are cis to each other. The molecules of (I) are linked by C—H···N hydrogen bonds into two dimensional sheets via dimers (Table 1, Fig. 2). Their packing motifs correspond to Etter's descriptors, R22(14) and R22(22) (Bernstein et al., 1995). The molecular packing is further stabilized by π-π stacking interactions between the benzene rings; C13—C13* (* = 2 - x,-0.5 + y,0.5 - z) distance is 3.6170 (4) Å
For related literature, see: Bernstein et al. (1995); Bradshaw, Bibby et al. (2002); Bradshaw, Chua et al. (2002); Brooker et al. (1940); Brownlee et al. (1992); Corey & Boger (1978); Hedge et al. (2006); Holbová et al. (1990); Hutchinson et al. (2002); Králová et al. (1992); Sidóová & Odlerová (1990).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids. | |
Fig. 2. A view of the unit cell packing of (I). |
C22H16N2S2 | F(000) = 776 |
Mr = 372.49 | Dx = 1.338 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 500 reflections |
a = 11.4142 (11) Å | θ = 1.0–25.0° |
b = 7.9101 (8) Å | µ = 0.30 mm−1 |
c = 20.553 (2) Å | T = 293 K |
β = 94.869 (2)° | Rectangular, yellow |
V = 1849.0 (3) Å3 | 0.3 × 0.2 × 0.1 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2730 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.026 |
Graphite monochromator | θmax = 25.0°, θmin = 1.8° |
φ and ω scans | h = −13→13 |
12852 measured reflections | k = −9→9 |
3260 independent reflections | l = −24→24 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | All H-atom parameters refined |
S = 1.15 | w = 1/[σ2(Fo2) + (0.0511P)2 + 0.8652P] where P = (Fo2 + 2Fc2)/3 |
3260 reflections | (Δ/σ)max = 0.001 |
237 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C22H16N2S2 | V = 1849.0 (3) Å3 |
Mr = 372.49 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.4142 (11) Å | µ = 0.30 mm−1 |
b = 7.9101 (8) Å | T = 293 K |
c = 20.553 (2) Å | 0.3 × 0.2 × 0.1 mm |
β = 94.869 (2)° |
Bruker SMART CCD area-detector diffractometer | 2730 reflections with I > 2σ(I) |
12852 measured reflections | Rint = 0.026 |
3260 independent reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.129 | All H-atom parameters refined |
S = 1.15 | Δρmax = 0.26 e Å−3 |
3260 reflections | Δρmin = −0.19 e Å−3 |
237 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.9027 (2) | 0.7127 (4) | −0.02928 (14) | 0.0446 (7) | |
C2 | 0.8276 (3) | 0.6166 (4) | 0.05881 (15) | 0.0467 (7) | |
C3 | 1.0029 (3) | 0.7342 (4) | 0.01428 (14) | 0.0452 (7) | |
C4 | 0.9041 (3) | 0.7583 (4) | −0.09522 (15) | 0.0483 (7) | |
C5 | 1.0078 (3) | 0.8232 (4) | −0.11692 (15) | 0.0531 (8) | |
C6 | 1.1065 (3) | 0.8403 (4) | −0.07267 (16) | 0.0520 (8) | |
H6 | 1.175 (3) | 0.877 (4) | −0.0863 (17) | 0.058 (10)* | |
C7 | 1.1080 (3) | 0.8004 (4) | −0.00666 (15) | 0.0455 (7) | |
C8 | 1.2178 (3) | 0.8258 (4) | 0.03667 (15) | 0.0466 (7) | |
C9 | 1.2497 (3) | 0.7210 (5) | 0.08930 (17) | 0.0526 (8) | |
H9 | 1.205 (3) | 0.630 (4) | 0.0988 (15) | 0.055 (9)* | |
C10 | 1.3538 (3) | 0.7431 (5) | 0.12779 (19) | 0.0594 (9) | |
H10 | 1.374 (4) | 0.662 (5) | 0.165 (2) | 0.082 (12)* | |
C11 | 1.4303 (3) | 0.8725 (5) | 0.11495 (17) | 0.0589 (9) | |
C12 | 1.5458 (4) | 0.8981 (9) | 0.1561 (3) | 0.0849 (14) | |
H12A | 1.535 (4) | 0.999 (7) | 0.185 (3) | 0.117 (17)* | |
H12B | 1.598 (5) | 0.901 (8) | 0.131 (3) | 0.13 (2)* | |
H12C | 1.561 (5) | 0.810 (7) | 0.191 (3) | 0.13 (2)* | |
C13 | 1.3986 (3) | 0.9782 (5) | 0.06248 (19) | 0.0616 (10) | |
H13 | 1.445 (3) | 1.068 (5) | 0.0526 (17) | 0.055 (9)* | |
C14 | 1.2947 (3) | 0.9560 (4) | 0.02381 (18) | 0.0547 (8) | |
H14 | 1.276 (3) | 1.041 (5) | −0.0146 (16) | 0.045 (9)* | |
C15 | 0.7422 (3) | 0.5403 (4) | 0.09969 (15) | 0.0481 (7) | |
C16 | 0.7639 (3) | 0.5262 (5) | 0.16663 (18) | 0.0615 (9) | |
H16 | 0.832 (3) | 0.560 (4) | 0.1869 (17) | 0.064 (11)* | |
C17 | 0.6819 (4) | 0.4536 (6) | 0.2037 (2) | 0.0732 (12) | |
H17 | 0.699 (3) | 0.449 (5) | 0.248 (2) | 0.075 (13)* | |
C18 | 0.5773 (4) | 0.3960 (6) | 0.1740 (2) | 0.0717 (11) | |
H18 | 0.522 (3) | 0.346 (4) | 0.1975 (16) | 0.065 (10)* | |
C19 | 0.5544 (3) | 0.4091 (5) | 0.1075 (2) | 0.0662 (10) | |
H19 | 0.479 (3) | 0.366 (5) | 0.0883 (19) | 0.082 (12)* | |
C20 | 0.6359 (3) | 0.4809 (5) | 0.07039 (19) | 0.0587 (9) | |
H20 | 0.621 (3) | 0.491 (4) | 0.0263 (18) | 0.059 (10)* | |
C21 | 0.8001 (3) | 0.7345 (5) | −0.13869 (16) | 0.0536 (8) | |
C22 | 1.1479 (5) | 0.9563 (8) | −0.2095 (3) | 0.0882 (15) | |
H22A | 1.171 (5) | 1.083 (8) | −0.183 (3) | 0.15 (2)* | |
H22B | 1.145 (3) | 0.976 (5) | −0.249 (2) | 0.077 (13)* | |
H22C | 1.204 (5) | 0.870 (7) | −0.201 (3) | 0.13 (2)* | |
N1 | 0.8054 (2) | 0.6455 (4) | −0.00331 (13) | 0.0476 (6) | |
N2 | 0.7190 (3) | 0.7147 (5) | −0.17417 (16) | 0.0748 (10) | |
S1 | 0.96953 (7) | 0.67111 (11) | 0.09166 (4) | 0.0508 (3) | |
S2 | 1.00579 (9) | 0.87246 (18) | −0.20032 (5) | 0.0879 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0435 (16) | 0.0431 (17) | 0.0476 (18) | 0.0030 (13) | 0.0067 (14) | 0.0010 (13) |
C2 | 0.0461 (17) | 0.0455 (18) | 0.0485 (18) | 0.0039 (14) | 0.0035 (14) | −0.0013 (14) |
C3 | 0.0469 (16) | 0.0458 (18) | 0.0431 (17) | 0.0071 (13) | 0.0044 (14) | 0.0016 (13) |
C4 | 0.0467 (18) | 0.0505 (19) | 0.0475 (17) | 0.0046 (14) | 0.0033 (14) | 0.0045 (15) |
C5 | 0.0530 (19) | 0.059 (2) | 0.0469 (18) | 0.0035 (15) | 0.0044 (15) | 0.0078 (15) |
C6 | 0.0445 (18) | 0.057 (2) | 0.054 (2) | −0.0019 (15) | 0.0057 (15) | 0.0068 (16) |
C7 | 0.0450 (16) | 0.0420 (17) | 0.0497 (18) | 0.0039 (13) | 0.0049 (14) | 0.0010 (14) |
C8 | 0.0453 (16) | 0.0473 (18) | 0.0476 (18) | 0.0040 (14) | 0.0071 (14) | −0.0036 (14) |
C9 | 0.0471 (18) | 0.054 (2) | 0.057 (2) | −0.0050 (16) | 0.0040 (16) | 0.0005 (16) |
C10 | 0.054 (2) | 0.067 (2) | 0.056 (2) | 0.0049 (18) | 0.0008 (17) | −0.002 (2) |
C11 | 0.0469 (18) | 0.073 (2) | 0.057 (2) | 0.0010 (17) | 0.0042 (16) | −0.0173 (18) |
C12 | 0.057 (3) | 0.114 (4) | 0.082 (3) | −0.009 (3) | −0.006 (2) | −0.018 (3) |
C13 | 0.054 (2) | 0.063 (2) | 0.069 (2) | −0.0132 (18) | 0.0139 (19) | −0.0110 (19) |
C14 | 0.053 (2) | 0.051 (2) | 0.061 (2) | 0.0006 (16) | 0.0084 (16) | −0.0004 (17) |
C15 | 0.0475 (17) | 0.0498 (18) | 0.0475 (18) | 0.0017 (14) | 0.0071 (14) | −0.0012 (14) |
C16 | 0.055 (2) | 0.077 (3) | 0.052 (2) | −0.0065 (19) | 0.0001 (17) | 0.0034 (18) |
C17 | 0.078 (3) | 0.091 (3) | 0.053 (2) | −0.008 (2) | 0.015 (2) | 0.012 (2) |
C18 | 0.066 (2) | 0.080 (3) | 0.072 (3) | −0.009 (2) | 0.024 (2) | 0.008 (2) |
C19 | 0.056 (2) | 0.074 (3) | 0.070 (3) | −0.0126 (19) | 0.0108 (19) | −0.004 (2) |
C20 | 0.056 (2) | 0.069 (2) | 0.051 (2) | −0.0031 (17) | 0.0042 (17) | −0.0007 (18) |
C21 | 0.0526 (19) | 0.064 (2) | 0.0448 (19) | 0.0011 (16) | 0.0080 (16) | 0.0060 (16) |
C22 | 0.077 (3) | 0.116 (5) | 0.074 (3) | −0.010 (3) | 0.022 (3) | 0.033 (3) |
N1 | 0.0458 (14) | 0.0511 (17) | 0.0459 (16) | 0.0019 (12) | 0.0037 (12) | 0.0006 (13) |
N2 | 0.0580 (19) | 0.106 (3) | 0.058 (2) | −0.0108 (18) | −0.0041 (16) | 0.0010 (18) |
S1 | 0.0471 (5) | 0.0616 (5) | 0.0436 (5) | −0.0010 (4) | 0.0030 (3) | 0.0013 (4) |
S2 | 0.0671 (6) | 0.1441 (12) | 0.0514 (6) | −0.0234 (6) | −0.0009 (5) | 0.0296 (6) |
C1—N1 | 1.379 (4) | C12—H12A | 1.01 (6) |
C1—C3 | 1.402 (4) | C12—H12B | 0.82 (6) |
C1—C4 | 1.404 (4) | C12—H12C | 1.01 (6) |
C2—N1 | 1.301 (4) | C13—C14 | 1.381 (5) |
C2—C15 | 1.470 (4) | C13—H13 | 0.92 (4) |
C2—S1 | 1.755 (3) | C14—H14 | 1.05 (3) |
C3—C7 | 1.409 (4) | C15—C16 | 1.382 (5) |
C3—S1 | 1.740 (3) | C15—C20 | 1.389 (5) |
C4—C5 | 1.397 (4) | C16—C17 | 1.380 (5) |
C4—C21 | 1.436 (5) | C16—H16 | 0.89 (4) |
C5—C6 | 1.394 (4) | C17—C18 | 1.372 (6) |
C5—S2 | 1.756 (3) | C17—H17 | 0.91 (4) |
C6—C7 | 1.392 (4) | C18—C19 | 1.373 (5) |
C6—H6 | 0.90 (4) | C18—H18 | 0.92 (4) |
C7—C8 | 1.487 (4) | C19—C20 | 1.374 (5) |
C8—C9 | 1.387 (4) | C19—H19 | 0.98 (4) |
C8—C14 | 1.393 (4) | C20—H20 | 0.91 (3) |
C9—C10 | 1.382 (5) | C21—N2 | 1.140 (4) |
C9—H9 | 0.91 (3) | C22—S2 | 1.778 (5) |
C10—C11 | 1.385 (5) | C22—H22A | 1.16 (7) |
C10—H10 | 1.01 (4) | C22—H22B | 0.83 (4) |
C11—C13 | 1.388 (5) | C22—H22C | 0.94 (6) |
C11—C12 | 1.518 (5) | ||
N1—C1—C3 | 116.1 (3) | H12A—C12—H12C | 98 (4) |
N1—C1—C4 | 123.2 (3) | H12B—C12—H12C | 112 (5) |
C3—C1—C4 | 120.7 (3) | C14—C13—C11 | 121.7 (3) |
N1—C2—C15 | 123.3 (3) | C14—C13—H13 | 117 (2) |
N1—C2—S1 | 115.6 (2) | C11—C13—H13 | 121 (2) |
C15—C2—S1 | 121.1 (2) | C13—C14—C8 | 120.6 (4) |
C1—C3—C7 | 121.3 (3) | C13—C14—H14 | 117.5 (19) |
C1—C3—S1 | 108.6 (2) | C8—C14—H14 | 121.9 (19) |
C7—C3—S1 | 130.1 (2) | C16—C15—C20 | 118.7 (3) |
C5—C4—C1 | 118.8 (3) | C16—C15—C2 | 122.0 (3) |
C5—C4—C21 | 121.8 (3) | C20—C15—C2 | 119.2 (3) |
C1—C4—C21 | 119.4 (3) | C17—C16—C15 | 120.7 (4) |
C6—C5—C4 | 119.2 (3) | C17—C16—H16 | 118 (2) |
C6—C5—S2 | 123.9 (2) | C15—C16—H16 | 121 (2) |
C4—C5—S2 | 116.9 (2) | C18—C17—C16 | 119.8 (4) |
C7—C6—C5 | 123.8 (3) | C18—C17—H17 | 122 (2) |
C7—C6—H6 | 116 (2) | C16—C17—H17 | 118 (2) |
C5—C6—H6 | 120 (2) | C17—C18—C19 | 120.2 (4) |
C6—C7—C3 | 116.2 (3) | C17—C18—H18 | 121 (2) |
C6—C7—C8 | 119.5 (3) | C19—C18—H18 | 118 (2) |
C3—C7—C8 | 124.2 (3) | C18—C19—C20 | 120.2 (4) |
C9—C8—C14 | 117.5 (3) | C18—C19—H19 | 117 (2) |
C9—C8—C7 | 122.6 (3) | C20—C19—H19 | 122 (2) |
C14—C8—C7 | 119.9 (3) | C19—C20—C15 | 120.4 (3) |
C10—C9—C8 | 121.8 (3) | C19—C20—H20 | 121 (2) |
C10—C9—H9 | 116 (2) | C15—C20—H20 | 119 (2) |
C8—C9—H9 | 122 (2) | N2—C21—C4 | 178.6 (3) |
C9—C10—C11 | 120.7 (4) | S2—C22—H22A | 116 (3) |
C9—C10—H10 | 119 (2) | S2—C22—H22B | 102 (3) |
C11—C10—H10 | 120 (2) | H22A—C22—H22B | 107 (4) |
C10—C11—C13 | 117.8 (3) | S2—C22—H22C | 109 (4) |
C10—C11—C12 | 121.6 (4) | H22A—C22—H22C | 114 (5) |
C13—C11—C12 | 120.6 (4) | H22B—C22—H22C | 107 (4) |
C11—C12—H12A | 107 (3) | C2—N1—C1 | 110.5 (3) |
C11—C12—H12B | 108 (4) | C3—S1—C2 | 89.17 (15) |
H12A—C12—H12B | 118 (5) | C5—S2—C22 | 104.5 (2) |
C11—C12—H12C | 113 (3) | ||
N1—C1—C3—C7 | 179.5 (3) | C6—C7—C8—C14 | 31.5 (4) |
C4—C1—C3—C7 | −0.6 (5) | C3—C7—C8—C14 | −149.7 (3) |
N1—C1—C3—S1 | −1.6 (3) | C14—C8—C9—C10 | −0.2 (5) |
C4—C1—C3—S1 | 178.3 (2) | C7—C8—C9—C10 | 177.9 (3) |
N1—C1—C4—C5 | −179.1 (3) | C7—C8—C14—C13 | −178.1 (3) |
C3—C1—C4—C5 | 1.0 (5) | N1—C2—C15—C16 | −173.5 (3) |
N1—C1—C4—C21 | −0.2 (5) | S1—C2—C15—C16 | 7.7 (4) |
C3—C1—C4—C21 | 179.9 (3) | N1—C2—C15—C20 | 6.3 (5) |
C1—C4—C5—C6 | 0.2 (5) | S1—C2—C15—C20 | −172.5 (3) |
C21—C4—C5—C6 | −178.7 (3) | C20—C15—C16—C17 | 0.4 (6) |
C1—C4—C5—S2 | 178.2 (2) | C2—C15—C16—C17 | −179.8 (4) |
C21—C4—C5—S2 | −0.7 (4) | C2—C15—C20—C19 | −180.0 (3) |
C4—C5—C6—C7 | −1.8 (5) | C15—C2—N1—C1 | −178.1 (3) |
S2—C5—C6—C7 | −179.7 (3) | S1—C2—N1—C1 | 0.7 (4) |
C5—C6—C7—C3 | 2.1 (5) | C3—C1—N1—C2 | 0.6 (4) |
C5—C6—C7—C8 | −179.1 (3) | C4—C1—N1—C2 | −179.3 (3) |
C1—C3—C7—C6 | −0.8 (4) | C1—C3—S1—C2 | 1.6 (2) |
S1—C3—C7—C6 | −179.5 (2) | C7—C3—S1—C2 | −179.6 (3) |
C1—C3—C7—C8 | −179.6 (3) | N1—C2—S1—C3 | −1.4 (3) |
S1—C3—C7—C8 | 1.6 (5) | C15—C2—S1—C3 | 177.5 (3) |
C6—C7—C8—C9 | −146.5 (3) | C6—C5—S2—C22 | −3.8 (4) |
C3—C7—C8—C9 | 32.3 (5) | C4—C5—S2—C22 | 178.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···N1i | 1.045 (5) | 2.685 (6) | 3.367 (5) | 123 |
Symmetry code: (i) −x+2, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C22H16N2S2 |
Mr | 372.49 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 11.4142 (11), 7.9101 (8), 20.553 (2) |
β (°) | 94.869 (2) |
V (Å3) | 1849.0 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.30 |
Crystal size (mm) | 0.3 × 0.2 × 0.1 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12852, 3260, 2730 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.129, 1.15 |
No. of reflections | 3260 |
No. of parameters | 237 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.26, −0.19 |
Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···N1i | 1.045 (5) | 2.685 (6) | 3.367 (5) | 123 |
Symmetry code: (i) −x+2, −y+2, −z. |
Benzothiazoles are bicyclic ring systems with multiple applications. They comprise a novel class of therapeutic compounds shown to exert a wide range of biological activities. Substituted derivatives of benzothiazole demonstrate several interesting pharmacological functions due to their potent capacity to interfere with cellular structures. For instance, the phenyl-substituted benzothiazoles show antitumor activity (Bradshaw, Bibby et al., 2002; Bradshaw, Chua et al., 2002; Hutchinson et al., 2002). They also act as antimicrobial (Holbová et al., 1990; Brownlee et al., 1992) and antimycobacterial (Sidóová & Odlerová, 1990) agents. In adition, they are used in the preparation of dyes (Brooker et al., 1940), organic synthesis of thermostable polymers (Corey & Boger, 1978) and as herbicides which inhibit photosynthesis (Králová et al., 1992). In this paper, we report the structure of the title compound, (I), which has been synthesized in our laboratory.
In (I), the benzothiazole and methylphenyl rings are inclined at an angle of 31.23 (8)° to each other (Fig. 1). The 2-subtituted phenyl ring is inclined with respect to benzothiazole ring at an angle of 7.74 (10)°. The methylthio and carbonitrile groups are cis to each other. The molecules of (I) are linked by C—H···N hydrogen bonds into two dimensional sheets via dimers (Table 1, Fig. 2). Their packing motifs correspond to Etter's descriptors, R22(14) and R22(22) (Bernstein et al., 1995). The molecular packing is further stabilized by π-π stacking interactions between the benzene rings; C13—C13* (* = 2 - x,-0.5 + y,0.5 - z) distance is 3.6170 (4) Å