Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801011230/ya6034sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801011230/ya6034Isup2.hkl |
CCDC reference: 170905
The title compound was obtained from the Janssen Research Foundation, Beerse, Belgium. The synthesis has been described by Venet et al. (1997). Single crystals were grown by slow evaporation from a solution in ethanol.
After checking their presence in the difference map, H atoms were placed at their geometrically calculated positions (the NH group has a planar environment), except for those of the methyl groups. The latter were found from a circular difference Fourier synthesis. All H atoms were allowed to ride on their parent atom and for the methyl groups to rotate around their local threefold axis. The isotropic displacement factors were fixed at 1.25 Ueq of their parent atoms.
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS (Siemens, 1996); data reduction: XSCANS (Siemens, 1996); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: PARST (Nardelli, 1983).
Fig. 1. Perspective view of a molecule of the title compound with atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. |
C21H23N5S | Dx = 1.232 Mg m−3 |
Mr = 377.51 | Cu Kα radiation, λ = 1.54184 Å |
Orthorhombic, P212121 | Cell parameters from 37 reflections |
a = 9.4442 (9) Å | θ = 5.6–26.6° |
b = 13.725 (1) Å | µ = 1.52 mm−1 |
c = 15.703 (1) Å | T = 293 K |
V = 2035.4 (3) Å3 | Prism, colourless |
Z = 4 | 0.30 × 0.24 × 0.08 mm |
F(000) = 800 |
Siemens P4 four-circle diffractometer | Rint = 0.023 |
ω/2θ scan | θmax = 69.2° |
Absorption correction: ψ scan XEMP (Siemens, 1989) | h = −9→9 |
Tmin = 0.625, Tmax = 0.886 | k = −16→16 |
3908 measured reflections | l = −19→19 |
3370 independent reflections | 3 standard reflections every 100 reflections |
2912 reflections with I > 2σ(I) | intensity decay: none |
Refinement on F2 | w = 1/[σ2(Fo2) + (0.0806P)2 + 0.5545P] where P = (Fo2 + 2Fc2)/3 |
Least-squares matrix: full | (Δ/σ)max = 0.001 |
R[F2 > 2σ(F2)] = 0.049 | Δρmax = 0.17 e Å−3 |
wR(F2) = 0.145 | Δρmin = −0.18 e Å−3 |
S = 1.07 | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin((2θ)]-1/4 |
3370 reflections | Extinction coefficient: 0.0023 (4) |
248 parameters | Absolute structure: Flack (1983). 847 Friedel pairs. |
H-atom parameters constrained | Absolute structure parameter: 0.01 (3) |
C21H23N5S | V = 2035.4 (3) Å3 |
Mr = 377.51 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 9.4442 (9) Å | µ = 1.52 mm−1 |
b = 13.725 (1) Å | T = 293 K |
c = 15.703 (1) Å | 0.30 × 0.24 × 0.08 mm |
Siemens P4 four-circle diffractometer | 2912 reflections with I > 2σ(I) |
Absorption correction: ψ scan XEMP (Siemens, 1989) | Rint = 0.023 |
Tmin = 0.625, Tmax = 0.886 | 3 standard reflections every 100 reflections |
3908 measured reflections | intensity decay: none |
3370 independent reflections |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.145 | Δρmax = 0.17 e Å−3 |
S = 1.07 | Δρmin = −0.18 e Å−3 |
3370 reflections | Absolute structure: Flack (1983). 847 Friedel pairs. |
248 parameters | Absolute structure parameter: 0.01 (3) |
x | y | z | Uiso*/Ueq | ||
N1 | 0.1766 (4) | 0.1146 (2) | 0.8725 (2) | 0.066 (1)* | |
C2 | 0.0559 (7) | 0.0493 (4) | 0.8739 (4) | 0.125 (3)* | |
C3 | 0.2986 (6) | 0.0693 (4) | 0.9117 (3) | 0.103 (2)* | |
C4 | 0.2092 (5) | 0.1578 (2) | 0.7885 (2) | 0.062 (1)* | |
C5 | 0.2273 (8) | 0.0851 (3) | 0.7160 (3) | 0.114 (2)* | |
C6 | 0.0959 (4) | 0.2346 (2) | 0.7671 (2) | 0.0520 (9)* | |
N7 | 0.0937 (3) | 0.3121 (2) | 0.8318 (2) | 0.0506 (8)* | |
C8 | 0.2038 (4) | 0.3508 (3) | 0.8740 (2) | 0.062 (1)* | |
N9 | 0.1679 (4) | 0.4273 (2) | 0.9196 (2) | 0.064 (1)* | |
C10 | 0.0262 (5) | 0.4375 (3) | 0.9061 (2) | 0.072 (2)* | |
C11 | −0.0211 (4) | 0.3677 (3) | 0.8520 (3) | 0.068 (1)* | |
C12 | 0.1127 (4) | 0.2780 (2) | 0.6789 (2) | 0.050 (1)* | |
C13 | 0.2216 (4) | 0.3422 (2) | 0.6600 (2) | 0.059 (1)* | |
C14 | 0.2385 (4) | 0.3791 (2) | 0.5791 (2) | 0.058 (1)* | |
C15 | 0.1489 (4) | 0.3521 (2) | 0.5141 (2) | 0.054 (1)* | |
C16 | 0.0402 (5) | 0.2875 (3) | 0.5310 (2) | 0.069 (1)* | |
C17 | 0.0230 (4) | 0.2514 (3) | 0.6135 (2) | 0.067 (1)* | |
N18 | 0.1695 (3) | 0.3955 (2) | 0.4336 (2) | 0.063 (1)* | |
C19 | 0.1512 (4) | 0.3510 (2) | 0.3572 (2) | 0.054 (1)* | |
S20 | 0.1975 (1) | 0.41953 (6) | 0.26549 (5) | 0.0671 (3)* | |
C21 | 0.1544 (4) | 0.3181 (3) | 0.2044 (2) | 0.057 (1)* | |
C22 | 0.1602 (5) | 0.3069 (3) | 0.1163 (2) | 0.070 (1)* | |
C23 | 0.1221 (5) | 0.2184 (3) | 0.0815 (2) | 0.074 (1)* | |
C24 | 0.0790 (4) | 0.1427 (3) | 0.1330 (2) | 0.071 (1)* | |
C25 | 0.0726 (4) | 0.1533 (3) | 0.2208 (2) | 0.063 (1)* | |
C26 | 0.1093 (4) | 0.2421 (2) | 0.2570 (2) | 0.053 (1)* | |
N27 | 0.1075 (3) | 0.2622 (2) | 0.3444 (2) | 0.0567 (9)* | |
H2A | 0.0390 | 0.0280 | 0.9312 | 0.157* | |
H2B | 0.0750 | −0.0061 | 0.8384 | 0.157* | |
H2C | −0.0262 | 0.0829 | 0.8529 | 0.157* | |
H3A | 0.2736 | 0.0463 | 0.9675 | 0.129* | |
H3B | 0.3737 | 0.1161 | 0.9163 | 0.129* | |
H3C | 0.3294 | 0.0154 | 0.8774 | 0.129* | |
H4 | 0.2993 | 0.1925 | 0.7944 | 0.077* | |
H5A | 0.2903 | 0.0340 | 0.7336 | 0.143* | |
H5B | 0.2663 | 0.1178 | 0.6673 | 0.143* | |
H5C | 0.1370 | 0.0578 | 0.7015 | 0.143* | |
H6 | 0.0037 | 0.2019 | 0.7689 | 0.065* | |
H8 | 0.2954 | 0.3262 | 0.8713 | 0.077* | |
H10 | −0.0301 | 0.4856 | 0.9305 | 0.090* | |
H11 | −0.1133 | 0.3595 | 0.8326 | 0.085* | |
H13 | 0.2844 | 0.3607 | 0.7027 | 0.074* | |
H14 | 0.3115 | 0.4229 | 0.5681 | 0.072* | |
H16 | −0.0209 | 0.2682 | 0.4877 | 0.086* | |
H17 | −0.0508 | 0.2084 | 0.6247 | 0.083* | |
H18 | 0.1961 | 0.4554 | 0.4329 | 0.079* | |
H22 | 0.1892 | 0.3581 | 0.0816 | 0.087* | |
H23 | 0.1256 | 0.2097 | 0.0228 | 0.092* | |
H24 | 0.0537 | 0.0835 | 0.1085 | 0.088* | |
H25 | 0.0441 | 0.1016 | 0.2550 | 0.078* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.081 (2) | 0.058 (2) | 0.059 (2) | −0.006 (2) | −0.012 (2) | 0.009 (1) |
C2 | 0.149 (5) | 0.112 (4) | 0.115 (4) | −0.063 (4) | −0.047 (4) | 0.058 (3) |
C3 | 0.114 (4) | 0.109 (3) | 0.086 (3) | 0.019 (4) | −0.016 (3) | 0.023 (3) |
C4 | 0.080 (3) | 0.053 (2) | 0.052 (2) | 0.000 (2) | 0.000 (2) | −0.001 (1) |
C5 | 0.198 (6) | 0.074 (3) | 0.071 (3) | 0.041 (4) | −0.014 (3) | −0.013 (2) |
C6 | 0.061 (2) | 0.049 (1) | 0.046 (1) | −0.010 (1) | −0.002 (2) | −0.002 (1) |
N7 | 0.057 (2) | 0.050 (1) | 0.045 (1) | −0.007 (1) | 0.003 (1) | 0.001 (1) |
C8 | 0.063 (2) | 0.064 (2) | 0.059 (2) | −0.006 (2) | −0.001 (2) | −0.009 (2) |
N9 | 0.086 (3) | 0.056 (1) | 0.050 (1) | −0.011 (2) | 0.004 (1) | −0.005 (1) |
C10 | 0.089 (3) | 0.064 (2) | 0.061 (2) | 0.008 (2) | 0.020 (2) | −0.004 (2) |
C11 | 0.059 (2) | 0.071 (2) | 0.073 (2) | 0.000 (2) | 0.008 (2) | −0.002 (2) |
C12 | 0.056 (2) | 0.048 (2) | 0.047 (2) | −0.008 (1) | −0.001 (1) | −0.001 (1) |
C13 | 0.066 (2) | 0.061 (2) | 0.050 (2) | −0.016 (2) | −0.007 (2) | 0.003 (1) |
C14 | 0.065 (2) | 0.055 (2) | 0.054 (2) | −0.014 (2) | 0.002 (2) | 0.002 (1) |
C15 | 0.068 (2) | 0.051 (2) | 0.043 (2) | −0.003 (2) | 0.004 (1) | 0.001 (1) |
C16 | 0.078 (3) | 0.084 (2) | 0.045 (2) | −0.025 (2) | −0.007 (2) | 0.004 (2) |
C17 | 0.072 (3) | 0.077 (2) | 0.050 (2) | −0.028 (2) | −0.001 (2) | 0.004 (2) |
N18 | 0.087 (2) | 0.056 (1) | 0.046 (1) | −0.012 (2) | 0.000 (1) | 0.003 (1) |
C19 | 0.061 (2) | 0.053 (2) | 0.048 (2) | 0.001 (2) | 0.003 (1) | 0.002 (1) |
S20 | 0.0939 (7) | 0.0577 (4) | 0.0497 (4) | −0.0013 (5) | 0.0044 (4) | 0.0080 (3) |
C21 | 0.060 (2) | 0.062 (2) | 0.049 (2) | 0.009 (2) | −0.002 (2) | 0.003 (1) |
C22 | 0.083 (3) | 0.078 (2) | 0.049 (2) | 0.010 (2) | −0.001 (2) | 0.005 (2) |
C23 | 0.079 (3) | 0.092 (3) | 0.050 (2) | 0.011 (2) | −0.004 (2) | −0.006 (2) |
C24 | 0.066 (2) | 0.080 (2) | 0.066 (2) | 0.007 (2) | −0.007 (2) | −0.021 (2) |
C25 | 0.061 (2) | 0.064 (2) | 0.064 (2) | 0.001 (2) | 0.004 (2) | −0.005 (2) |
C26 | 0.051 (2) | 0.058 (2) | 0.049 (2) | 0.005 (1) | −0.002 (1) | 0.000 (1) |
N27 | 0.063 (2) | 0.058 (2) | 0.049 (1) | 0.000 (1) | 0.002 (1) | −0.001 (1) |
N1—C2 | 1.449 (7) | C12—C17 | 1.379 (5) |
N1—C3 | 1.447 (6) | C13—C14 | 1.378 (5) |
N1—C4 | 1.480 (4) | C13—H13 | 0.930 |
C2—H2A | 0.960 | C14—C15 | 1.376 (5) |
C2—H2B | 0.960 | C14—H14 | 0.930 |
C2—H2C | 0.960 | C15—C16 | 1.382 (5) |
C3—H3A | 0.960 | C15—N18 | 1.411 (4) |
C3—H3B | 0.960 | C16—C17 | 1.397 (5) |
C3—H3C | 0.960 | C16—H16 | 0.930 |
C4—C5 | 1.523 (6) | C17—H17 | 0.930 |
C4—C6 | 1.539 (5) | N18—C19 | 1.357 (4) |
C4—H4 | 0.980 | N18—H18 | 0.860 |
C5—H5A | 0.960 | C19—S20 | 1.775 (3) |
C5—H5B | 0.960 | C19—N27 | 1.303 (4) |
C5—H5C | 0.960 | S20—C21 | 1.739 (4) |
C6—N7 | 1.472 (4) | C21—C22 | 1.393 (5) |
C6—C12 | 1.517 (4) | C21—C26 | 1.397 (5) |
C6—H6 | 0.980 | C22—C23 | 1.380 (6) |
N7—C8 | 1.342 (5) | C22—H22 | 0.930 |
N7—C11 | 1.363 (5) | C23—C24 | 1.378 (6) |
C8—N9 | 1.316 (5) | C23—H23 | 0.930 |
C8—H8 | 0.930 | C24—C25 | 1.388 (5) |
N9—C10 | 1.362 (6) | C24—H24 | 0.930 |
C10—C11 | 1.356 (6) | C25—C26 | 1.389 (5) |
C10—H10 | 0.930 | C25—H25 | 0.930 |
C11—H11 | 0.930 | C26—N27 | 1.401 (4) |
C12—C13 | 1.387 (5) | ||
C2—N1—C3 | 110.8 (4) | C10—C11—H11 | 126.9 |
C2—N1—C4 | 115.1 (3) | C6—C12—C13 | 121.5 (3) |
C3—N1—C4 | 112.7 (3) | C6—C12—C17 | 120.8 (3) |
N1—C2—H2A | 109.5 | C13—C12—C17 | 117.7 (3) |
N1—C2—H2B | 109.5 | C12—C13—C14 | 121.1 (3) |
N1—C2—H2C | 109.5 | C12—C13—H13 | 119.4 |
H2A—C2—H2B | 109.5 | C14—C13—H13 | 119.4 |
H2A—C2—H2C | 109.5 | C13—C14—C15 | 120.9 (3) |
H2B—C2—H2C | 109.5 | C13—C14—H14 | 119.6 |
N1—C3—H3A | 109.5 | C15—C14—H14 | 119.6 |
N1—C3—H3B | 109.5 | C14—C15—C16 | 119.2 (3) |
N1—C3—H3C | 109.5 | C14—C15—N18 | 117.7 (3) |
H3A—C3—H3B | 109.5 | C16—C15—N18 | 123.0 (3) |
H3A—C3—H3C | 109.5 | C15—C16—C17 | 119.4 (3) |
H3B—C3—H3C | 109.5 | C15—C16—H16 | 120.3 |
N1—C4—C5 | 115.3 (3) | C17—C16—H16 | 120.3 |
N1—C4—C6 | 108.9 (3) | C12—C17—C16 | 121.7 (3) |
N1—C4—H4 | 106.9 | C12—C17—H17 | 119.2 |
C5—C4—C6 | 111.3 (3) | C16—C17—H17 | 119.2 |
C5—C4—H4 | 106.9 | C15—N18—C19 | 125.8 (3) |
C6—C4—H4 | 106.9 | C15—N18—H18 | 117.1 |
C4—C5—H5A | 109.5 | C19—N18—H18 | 117.1 |
C4—C5—H5B | 109.5 | N18—C19—S20 | 116.6 (2) |
C4—C5—H5C | 109.5 | N18—C19—N27 | 126.7 (3) |
H5A—C5—H5B | 109.5 | S20—C19—N27 | 116.7 (2) |
H5A—C5—H5C | 109.5 | C19—S20—C21 | 88.1 (2) |
H5B—C5—H5C | 109.5 | S20—C21—C22 | 128.8 (3) |
C4—C6—N7 | 110.8 (2) | S20—C21—C26 | 110.0 (3) |
C4—C6—C12 | 113.3 (3) | C22—C21—C26 | 121.2 (3) |
C4—C6—H6 | 107.4 | C21—C22—C23 | 118.7 (3) |
N7—C6—C12 | 110.4 (2) | C21—C22—H22 | 120.7 |
N7—C6—H6 | 107.4 | C23—C22—H22 | 120.7 |
C12—C6—H6 | 107.4 | C22—C23—C24 | 120.6 (4) |
C6—N7—C8 | 128.0 (3) | C22—C23—H23 | 119.7 |
C6—N7—C11 | 125.2 (3) | C24—C23—H23 | 119.7 |
C8—N7—C11 | 106.3 (3) | C23—C24—C25 | 121.1 (3) |
N7—C8—N9 | 112.6 (3) | C23—C24—H24 | 119.4 |
N7—C8—H8 | 123.7 | C25—C24—H24 | 119.4 |
N9—C8—H8 | 123.7 | C24—C25—C26 | 119.2 (3) |
C8—N9—C10 | 104.5 (3) | C24—C25—H25 | 120.4 |
N9—C10—C11 | 110.4 (4) | C26—C25—H25 | 120.4 |
N9—C10—H10 | 124.8 | C21—C26—C25 | 119.3 (3) |
C11—C10—H10 | 124.8 | C21—C26—N27 | 115.9 (3) |
N7—C11—C10 | 106.2 (3) | C25—C26—N27 | 124.8 (3) |
N7—C11—H11 | 126.9 | C19—N27—C26 | 109.3 (3) |
C3—N1—C2—H2A | 54.2 | C6—C12—C13—C14 | 178.1 (3) |
C3—N1—C2—H2B | −65.8 | C6—C12—C13—H13 | −1.9 |
C3—N1—C2—H2C | 174.2 | C17—C12—C13—C14 | 0.8 (5) |
C4—N1—C2—H2A | −176.5 | C17—C12—C13—H13 | −179.2 |
C4—N1—C2—H2B | 63.5 | C6—C12—C17—C16 | −177.4 (3) |
C4—N1—C2—H2C | −56.5 | C6—C12—C17—H17 | 2.6 |
C2—N1—C3—H3A | −53.2 | C13—C12—C17—C16 | 0.0 (5) |
C2—N1—C3—H3B | −173.2 | C13—C12—C17—H17 | 180.0 |
C2—N1—C3—H3C | 66.8 | C12—C13—C14—C15 | −1.0 (5) |
C4—N1—C3—H3A | 176.2 | C12—C13—C14—H14 | 179.0 |
C4—N1—C3—H3B | 56.2 | H13—C13—C14—C15 | 179.0 |
C4—N1—C3—H3C | −63.8 | H13—C13—C14—H14 | −1.0 |
C2—N1—C4—C5 | −53.5 (5) | C13—C14—C15—C16 | 0.4 (5) |
C2—N1—C4—C6 | 72.5 (4) | C13—C14—C15—N18 | 177.8 (3) |
C2—N1—C4—H4 | −172.3 | H14—C14—C15—C16 | −179.6 |
C3—N1—C4—C5 | 74.8 (4) | H14—C14—C15—N18 | −2.2 |
C3—N1—C4—C6 | −159.2 (3) | C14—C15—C16—C17 | 0.4 (5) |
C3—N1—C4—H4 | −43.9 | C14—C15—C16—H16 | −179.6 |
N1—C4—C5—H5A | −48.7 | N18—C15—C16—C17 | −176.9 (3) |
N1—C4—C5—H5B | −168.6 | N18—C15—C16—H16 | 3.1 |
N1—C4—C5—H5C | 71.4 | C14—C15—N18—C19 | 144.2 (3) |
C6—C4—C5—H5A | −173.4 | C14—C15—N18—H18 | −35.8 |
C6—C4—C5—H5B | 66.6 | C16—C15—N18—C19 | −38.5 (5) |
C6—C4—C5—H5C | −53.4 | C16—C15—N18—H18 | 141.5 |
H4—C4—C5—H5A | 70.1 | C15—C16—C17—C12 | −0.6 (6) |
H4—C4—C5—H5B | −49.9 | C15—C16—C17—H17 | 179.4 |
H4—C4—C5—H5C | −169.9 | H16—C16—C17—C12 | 179.4 |
N1—C4—C6—N7 | 59.8 (3) | H16—C16—C17—H17 | −0.6 |
N1—C4—C6—C12 | −175.4 (3) | C15—N18—C19—S20 | −175.3 (3) |
N1—C4—C6—H6 | −57.1 | C15—N18—C19—N27 | 2.3 (5) |
C5—C4—C6—N7 | −171.9 (3) | H18—N18—C19—S20 | 4.7 |
C5—C4—C6—C12 | −47.2 (4) | H18—N18—C19—N27 | −177.7 |
C5—C4—C6—H6 | 71.2 | N18—C19—S20—C21 | 177.6 (3) |
H4—C4—C6—N7 | −55.4 | N27—C19—S20—C21 | −0.3 (3) |
H4—C4—C6—C12 | 69.3 | N18—C19—N27—C26 | −177.2 (3) |
H4—C4—C6—H6 | −172.3 | S20—C19—N27—C26 | 0.5 (4) |
C4—C6—N7—C8 | 36.3 (4) | C19—S20—C21—C22 | −180.0 (4) |
C4—C6—N7—C11 | −153.1 (3) | C19—S20—C21—C26 | 0.1 (3) |
C12—C6—N7—C8 | −90.0 (4) | S20—C21—C22—C23 | 179.2 (3) |
C12—C6—N7—C11 | 80.5 (4) | S20—C21—C22—H22 | −0.8 |
H6—C6—N7—C8 | 153.3 | C26—C21—C22—C23 | −0.9 (6) |
H6—C6—N7—C11 | −36.2 | C26—C21—C22—H22 | 179.1 |
C4—C6—C12—C13 | −72.1 (4) | S20—C21—C26—C25 | −178.6 (3) |
C4—C6—C12—C17 | 105.1 (4) | S20—C21—C26—N27 | 0.2 (4) |
N7—C6—C12—C13 | 52.8 (4) | C22—C21—C26—C25 | 1.4 (5) |
N7—C6—C12—C17 | −130.0 (3) | C22—C21—C26—N27 | −179.8 (3) |
H6—C6—C12—C13 | 169.5 | C21—C22—C23—C24 | 0.1 (6) |
H6—C6—C12—C17 | −13.2 | C21—C22—C23—H23 | −179.9 |
C6—N7—C8—N9 | 171.8 (3) | H22—C22—C23—C24 | −179.9 |
C6—N7—C8—H8 | −8.2 | H22—C22—C23—H23 | 0.1 |
C11—N7—C8—N9 | −0.1 (4) | C22—C23—C24—C25 | 0.0 (6) |
C11—N7—C8—H8 | 179.9 | C22—C23—C24—H24 | −180.0 |
C6—N7—C11—C10 | −172.5 (3) | H23—C23—C24—C25 | −180.0 |
C6—N7—C11—H11 | 7.5 | H23—C23—C24—H24 | 0.0 |
C8—N7—C11—C10 | −0.3 (4) | C23—C24—C25—C26 | 0.6 (6) |
C8—N7—C11—H11 | 179.8 | C23—C24—C25—H25 | −179.4 |
N7—C8—N9—C10 | 0.4 (4) | H24—C24—C25—C26 | −179.4 |
H8—C8—N9—C10 | −179.6 | H24—C24—C25—H25 | 0.6 |
C8—N9—C10—C11 | −0.6 (4) | C24—C25—C26—C21 | −1.3 (5) |
C8—N9—C10—H10 | 179.4 | C24—C25—C26—N27 | −180.0 (3) |
N9—C10—C11—N7 | 0.5 (4) | H25—C25—C26—C21 | 178.7 |
N9—C10—C11—H11 | −179.5 | H25—C25—C26—N27 | 0.1 |
H10—C10—C11—N7 | −179.5 | C21—C26—N27—C19 | −0.4 (4) |
H10—C10—C11—H11 | 0.5 | C25—C26—N27—C19 | 178.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N18—H18···N9i | 0.86 | 2.07 | 2.884 (4) | 158 |
C22—H22···N9ii | 0.93 | 2.72 | 3.503 (5) | 142 |
C23—H23···N1ii | 0.93 | 2.74 | 3.614 (5) | 157 |
Symmetry codes: (i) −x+1/2, −y+1, z−1/2; (ii) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | C21H23N5S |
Mr | 377.51 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 9.4442 (9), 13.725 (1), 15.703 (1) |
V (Å3) | 2035.4 (3) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 1.52 |
Crystal size (mm) | 0.30 × 0.24 × 0.08 |
Data collection | |
Diffractometer | Siemens P4 four-circle diffractometer |
Absorption correction | ψ scan XEMP (Siemens, 1989) |
Tmin, Tmax | 0.625, 0.886 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3908, 3370, 2912 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.145, 1.07 |
No. of reflections | 3370 |
No. of parameters | 248 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.18 |
Absolute structure | Flack (1983). 847 Friedel pairs. |
Absolute structure parameter | 0.01 (3) |
Computer programs: XSCANS (Siemens, 1996), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), DIAMOND (Bergerhoff, 1996), PARST (Nardelli, 1983).
D—H···A | D—H | H···A | D···A | D—H···A |
N18—H18···N9i | 0.86 | 2.07 | 2.884 (4) | 158 |
C22—H22···N9ii | 0.93 | 2.72 | 3.503 (5) | 142 |
C23—H23···N1ii | 0.93 | 2.74 | 3.614 (5) | 157 |
Symmetry codes: (i) −x+1/2, −y+1, z−1/2; (ii) x, y, z−1. |
All-trans-retinoic-acid (ATRA) is a metabolite of retinol (Vitamin A) which is involved in growth and epithelial differentiation in mammals. However the potency of ATRA is strongly attenuated by its rapid metabolism involving the stage of hydroxylation, mediated by a cytochrome dependent P-450 system (Leo et al., 1989). The P-450 system is inhibited by the title compound, which leads to increased plasma levels of ATRA.
All four rings in the molecule of the title compound (Fig. 1) are essentially planar. The imidazolyl ring is almost perpendicular to the phenylene ring [dihedral angle 80.2 (1)°], the phenylene ring and the benzothiazolyl ring are twisted with a dihedral angle of 37.12 (8)°. The secondary amine group is almost coplanar with the benzothiazolyl moiety [dihedral angle 4.3 (2)°] but is twisted with respect to the phenylene ring [dihedral angle 37.3 (3)°]. The degree of coplanarity and conjugation with the π-electron systems of the aromatic rings is reflected in the C—N bond lengths. The C19—N18 bond [1.357 (4)°] is significantly shorter than the C15—N18 bond [1.411 (4)°].
The N18—H18···N9 hydrogen bond [N18—H18···N9i 2.07 Å, N18···N9i 2.884 (4) Å, N18—H18···N9i 158 ° (D—H distance not normalized); symmetry code (i): 1/2 - x, 1 - y, z - 1/2] links two molecules related by the 21(z) screw axis, thus giving rise to infinite one-dimensional chains stretching along the c axis of the crystal.