Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103023205/ln1181sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270103023205/ln1181Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270103023205/ln1181IIsup3.hkl |
CCDC references: 229097; 229098
The title compounds were synthesized using the Gewald reaction (Gewald et al., 1966). For compound (I), o-cyanotoluidine was refluxed with ethyl methyl ketone in the presence of sulfur, dimethylamine and ethanol at 313–323 K for 1 h. The product was then reacted with p-(dimethylamino)benzaldehyde in an equimolar ratio in the presence of ethanol, which yielded (I). This was then purified and crystallized from a solution in N,N-dimethylformamide and ethanol (1:2) by slow evaporation. Crystals (m.p. 419 K) were obtained after three weeks and were used for single-crystal data collection. For compound (II), a similar procedure was followed using cyclohexanone in place of ethyl methyl ketone and p-cyanotoluidine in place of o-cyanotoluidine. The compound was purified and crystallized by the same procedure as followed for (I) (m.p. 497 K).
For both compounds, the position of the amide H atom was located from a difference Fourier map and was refined freely along with isotropic displacement parameters. The methyl H atoms were constrained to an ideal geometry (C—H = 0.96 Å), with Uiso values of 1.5Ueq(C), but were allowed to rotate freely about the C—C bond. All remaining H atoms were placed in idealized positions (C—H = 0.93–0.97 Å) and constrained to ride on their parent atoms, with Uiso(H) values of 1.2Ueq(C).
For both compounds, data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
C23H25N3OS | Z = 2 |
Mr = 391.53 | F(000) = 416 |
Triclinic, P1 | Dx = 1.274 Mg m−3 |
Hall symbol: -P 1 | Melting point: 419 K |
a = 7.8352 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.7300 (13) Å | Cell parameters from 835 reflections |
c = 13.1342 (15) Å | θ = 2.3–21.2° |
α = 94.222 (2)° | µ = 0.18 mm−1 |
β = 99.965 (2)° | T = 293 K |
γ = 108.593 (2)° | Prism, red |
V = 1020.9 (2) Å3 | 0.20 × 0.20 × 0.20 mm |
Bruker SMART CCD area-detector diffractometer | 3725 independent reflections |
Radiation source: sealed tube | 1678 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.086 |
ϕ and ω scans | θmax = 25.4°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −9→9 |
Tmin = 0.908, Tmax = 0.966 | k = −12→12 |
10235 measured reflections | l = −15→15 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0417P)2] where P = (Fo2 + 2Fc2)/3 |
3725 reflections | (Δ/σ)max < 0.001 |
262 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C23H25N3OS | γ = 108.593 (2)° |
Mr = 391.53 | V = 1020.9 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.8352 (9) Å | Mo Kα radiation |
b = 10.7300 (13) Å | µ = 0.18 mm−1 |
c = 13.1342 (15) Å | T = 293 K |
α = 94.222 (2)° | 0.20 × 0.20 × 0.20 mm |
β = 99.965 (2)° |
Bruker SMART CCD area-detector diffractometer | 3725 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | 1678 reflections with I > 2σ(I) |
Tmin = 0.908, Tmax = 0.966 | Rint = 0.086 |
10235 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 0 restraints |
wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | Δρmax = 0.20 e Å−3 |
3725 reflections | Δρmin = −0.19 e Å−3 |
262 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. |
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 | 0.45958 (14) | 0.11614 (10) | 0.91004 (8) | 0.0566 (4) | |
N1 | 0.4066 (5) | 0.4322 (4) | 0.6994 (3) | 0.0537 (10) | |
N2 | 0.5671 (4) | 0.3821 (3) | 0.8896 (2) | 0.0465 (8) | |
N3 | 1.1599 (4) | 0.8933 (3) | 1.2015 (3) | 0.0582 (9) | |
O1 | 0.1575 (4) | 0.2684 (2) | 0.6062 (2) | 0.0605 (8) | |
C1 | 0.3046 (5) | 0.0072 (4) | 0.8072 (3) | 0.0487 (10) | |
C2 | 0.2489 (5) | 0.0714 (4) | 0.7284 (3) | 0.0461 (10) | |
C3 | 0.3344 (5) | 0.2130 (4) | 0.7515 (3) | 0.0409 (9) | |
C4 | 0.4570 (5) | 0.2535 (4) | 0.8472 (3) | 0.0434 (10) | |
C5 | 0.2512 (5) | −0.1394 (4) | 0.8118 (3) | 0.0728 (13) | |
H5A | 0.1518 | −0.1863 | 0.7543 | 0.109* | |
H5B | 0.2128 | −0.1582 | 0.8763 | 0.109* | |
H5C | 0.3550 | −0.1674 | 0.8080 | 0.109* | |
C6 | 0.1223 (5) | −0.0025 (4) | 0.6274 (3) | 0.0637 (12) | |
H6A | 0.0932 | −0.0963 | 0.6286 | 0.096* | |
H6B | 0.1818 | 0.0227 | 0.5704 | 0.096* | |
H6C | 0.0111 | 0.0189 | 0.6188 | 0.096* | |
C7 | 0.2899 (5) | 0.3061 (4) | 0.6797 (3) | 0.0440 (10) | |
C8 | 0.4023 (5) | 0.5383 (4) | 0.6427 (3) | 0.0446 (10) | |
C9 | 0.5653 (5) | 0.6229 (4) | 0.6236 (3) | 0.0468 (10) | |
C10 | 0.5614 (6) | 0.7287 (4) | 0.5700 (3) | 0.0652 (13) | |
H10 | 0.6703 | 0.7862 | 0.5573 | 0.078* | |
C11 | 0.3969 (7) | 0.7498 (4) | 0.5350 (3) | 0.0716 (14) | |
H11 | 0.3959 | 0.8216 | 0.4996 | 0.086* | |
C12 | 0.2354 (6) | 0.6647 (4) | 0.5526 (3) | 0.0657 (13) | |
H12 | 0.1248 | 0.6781 | 0.5280 | 0.079* | |
C13 | 0.2363 (6) | 0.5593 (4) | 0.6068 (3) | 0.0574 (11) | |
H13 | 0.1268 | 0.5025 | 0.6194 | 0.069* | |
C14 | 0.7452 (5) | 0.5998 (4) | 0.6579 (3) | 0.0699 (13) | |
H14A | 0.7846 | 0.6219 | 0.7323 | 0.105* | |
H14B | 0.8365 | 0.6547 | 0.6250 | 0.105* | |
H14C | 0.7291 | 0.5082 | 0.6383 | 0.105* | |
C15 | 0.6727 (5) | 0.4037 (4) | 0.9796 (3) | 0.0484 (11) | |
H15 | 0.6679 | 0.3304 | 1.0141 | 0.058* | |
C16 | 0.7976 (5) | 0.5299 (4) | 1.0323 (3) | 0.0441 (10) | |
C17 | 0.9062 (5) | 0.5376 (4) | 1.1308 (3) | 0.0524 (11) | |
H17 | 0.8954 | 0.4600 | 1.1603 | 0.063* | |
C18 | 1.0276 (5) | 0.6550 (4) | 1.1852 (3) | 0.0507 (11) | |
H18 | 1.0993 | 0.6548 | 1.2495 | 0.061* | |
C19 | 1.0459 (5) | 0.7756 (4) | 1.1459 (3) | 0.0459 (10) | |
C20 | 0.9382 (5) | 0.7680 (4) | 1.0463 (3) | 0.0530 (11) | |
H20 | 0.9488 | 0.8452 | 1.0161 | 0.064* | |
C21 | 0.8186 (5) | 0.6495 (4) | 0.9933 (3) | 0.0529 (11) | |
H21 | 0.7482 | 0.6488 | 0.9284 | 0.063* | |
C22 | 1.1799 (6) | 1.0188 (4) | 1.1603 (3) | 0.0745 (14) | |
H22A | 1.2247 | 1.0170 | 1.0969 | 0.112* | |
H22B | 1.2656 | 1.0905 | 1.2106 | 0.112* | |
H22C | 1.0626 | 1.0314 | 1.1464 | 0.112* | |
C23 | 1.2700 (5) | 0.8971 (4) | 1.3033 (3) | 0.0676 (13) | |
H23A | 1.1905 | 0.8600 | 1.3494 | 0.101* | |
H23B | 1.3427 | 0.9875 | 1.3311 | 0.101* | |
H23C | 1.3497 | 0.8465 | 1.2967 | 0.101* | |
H1N | 0.482 (4) | 0.451 (3) | 0.749 (2) | 0.037 (13)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0650 (8) | 0.0543 (8) | 0.0487 (7) | 0.0224 (6) | −0.0011 (6) | 0.0152 (6) |
N1 | 0.052 (3) | 0.052 (3) | 0.048 (3) | 0.013 (2) | −0.008 (2) | 0.015 (2) |
N2 | 0.044 (2) | 0.054 (2) | 0.039 (2) | 0.0186 (18) | −0.0018 (17) | 0.0053 (17) |
N3 | 0.062 (2) | 0.052 (2) | 0.051 (2) | 0.0140 (19) | −0.0030 (19) | 0.0043 (19) |
O1 | 0.0601 (18) | 0.0600 (19) | 0.0527 (18) | 0.0185 (15) | −0.0092 (15) | 0.0128 (15) |
C1 | 0.052 (3) | 0.045 (3) | 0.048 (2) | 0.019 (2) | 0.004 (2) | 0.009 (2) |
C2 | 0.044 (2) | 0.046 (3) | 0.047 (3) | 0.016 (2) | 0.004 (2) | 0.004 (2) |
C3 | 0.037 (2) | 0.050 (3) | 0.038 (2) | 0.017 (2) | 0.0082 (19) | 0.013 (2) |
C4 | 0.046 (2) | 0.049 (3) | 0.039 (2) | 0.018 (2) | 0.010 (2) | 0.011 (2) |
C5 | 0.078 (3) | 0.055 (3) | 0.079 (3) | 0.021 (3) | −0.001 (3) | 0.018 (3) |
C6 | 0.065 (3) | 0.053 (3) | 0.061 (3) | 0.016 (2) | −0.008 (2) | 0.003 (2) |
C7 | 0.041 (3) | 0.051 (3) | 0.038 (2) | 0.015 (2) | 0.005 (2) | 0.004 (2) |
C8 | 0.052 (3) | 0.046 (3) | 0.036 (2) | 0.018 (2) | 0.004 (2) | 0.009 (2) |
C9 | 0.052 (3) | 0.040 (2) | 0.043 (2) | 0.010 (2) | 0.007 (2) | 0.002 (2) |
C10 | 0.076 (4) | 0.053 (3) | 0.054 (3) | 0.004 (3) | 0.013 (2) | 0.013 (2) |
C11 | 0.096 (4) | 0.057 (3) | 0.059 (3) | 0.028 (3) | 0.000 (3) | 0.022 (2) |
C12 | 0.068 (3) | 0.064 (3) | 0.062 (3) | 0.030 (3) | −0.010 (2) | 0.006 (3) |
C13 | 0.061 (3) | 0.057 (3) | 0.053 (3) | 0.021 (2) | 0.006 (2) | 0.009 (2) |
C14 | 0.050 (3) | 0.080 (3) | 0.080 (3) | 0.019 (2) | 0.015 (2) | 0.019 (3) |
C15 | 0.052 (3) | 0.052 (3) | 0.045 (3) | 0.020 (2) | 0.009 (2) | 0.017 (2) |
C16 | 0.046 (3) | 0.054 (3) | 0.039 (2) | 0.025 (2) | 0.007 (2) | 0.012 (2) |
C17 | 0.058 (3) | 0.052 (3) | 0.047 (3) | 0.021 (2) | 0.002 (2) | 0.016 (2) |
C18 | 0.050 (3) | 0.059 (3) | 0.044 (3) | 0.024 (2) | −0.001 (2) | 0.012 (2) |
C19 | 0.046 (3) | 0.052 (3) | 0.043 (3) | 0.020 (2) | 0.009 (2) | 0.007 (2) |
C20 | 0.067 (3) | 0.049 (3) | 0.046 (3) | 0.023 (2) | 0.008 (2) | 0.017 (2) |
C21 | 0.061 (3) | 0.064 (3) | 0.036 (2) | 0.027 (3) | 0.002 (2) | 0.012 (2) |
C22 | 0.088 (4) | 0.060 (3) | 0.073 (3) | 0.021 (3) | 0.016 (3) | 0.015 (3) |
C23 | 0.064 (3) | 0.071 (3) | 0.058 (3) | 0.021 (2) | −0.002 (2) | −0.004 (2) |
S1—C1 | 1.721 (4) | C10—H10 | 0.9300 |
S1—C4 | 1.745 (4) | C11—C12 | 1.373 (5) |
N1—C7 | 1.346 (5) | C11—H11 | 0.9300 |
N1—C8 | 1.411 (5) | C12—C13 | 1.381 (5) |
N1—H1N | 0.76 (3) | C12—H12 | 0.9300 |
N2—C15 | 1.278 (4) | C13—H13 | 0.9300 |
N2—C4 | 1.386 (4) | C14—H14A | 0.9600 |
N3—C19 | 1.359 (4) | C14—H14B | 0.9600 |
N3—C23 | 1.449 (4) | C14—H14C | 0.9600 |
N3—C22 | 1.461 (4) | C15—C16 | 1.434 (5) |
O1—C7 | 1.225 (4) | C15—H15 | 0.9300 |
C1—C2 | 1.370 (4) | C16—C21 | 1.388 (5) |
C1—C5 | 1.502 (5) | C16—C17 | 1.401 (4) |
C2—C3 | 1.435 (5) | C17—C18 | 1.367 (5) |
C2—C6 | 1.503 (5) | C17—H17 | 0.9300 |
C3—C4 | 1.389 (4) | C18—C19 | 1.402 (5) |
C3—C7 | 1.502 (5) | C18—H18 | 0.9300 |
C5—H5A | 0.9600 | C19—C20 | 1.411 (5) |
C5—H5B | 0.9600 | C20—C21 | 1.365 (5) |
C5—H5C | 0.9600 | C20—H20 | 0.9300 |
C6—H6A | 0.9600 | C21—H21 | 0.9300 |
C6—H6B | 0.9600 | C22—H22A | 0.9600 |
C6—H6C | 0.9600 | C22—H22B | 0.9600 |
C8—C9 | 1.387 (5) | C22—H22C | 0.9600 |
C8—C13 | 1.398 (5) | C23—H23A | 0.9600 |
C9—C10 | 1.385 (5) | C23—H23B | 0.9600 |
C9—C14 | 1.507 (5) | C23—H23C | 0.9600 |
C10—C11 | 1.386 (5) | ||
C1—S1—C4 | 92.35 (19) | C10—C11—H11 | 120.0 |
C7—N1—C8 | 128.1 (4) | C11—C12—C13 | 120.3 (4) |
C7—N1—H1N | 118 (3) | C11—C12—H12 | 119.8 |
C8—N1—H1N | 114 (3) | C13—C12—H12 | 119.8 |
C15—N2—C4 | 119.7 (3) | C12—C13—C8 | 119.8 (4) |
C19—N3—C23 | 120.4 (3) | C12—C13—H13 | 120.1 |
C19—N3—C22 | 121.6 (3) | C8—C13—H13 | 120.1 |
C23—N3—C22 | 117.9 (3) | C9—C14—H14A | 109.5 |
C2—C1—C5 | 128.7 (3) | C9—C14—H14B | 109.5 |
C2—C1—S1 | 112.1 (3) | H14A—C14—H14B | 109.5 |
C5—C1—S1 | 119.2 (3) | C9—C14—H14C | 109.5 |
C1—C2—C3 | 112.3 (3) | H14A—C14—H14C | 109.5 |
C1—C2—C6 | 122.1 (3) | H14B—C14—H14C | 109.5 |
C3—C2—C6 | 125.4 (3) | N2—C15—C16 | 126.3 (3) |
C4—C3—C2 | 113.1 (3) | N2—C15—H15 | 116.9 |
C4—C3—C7 | 124.2 (3) | C16—C15—H15 | 116.9 |
C2—C3—C7 | 122.7 (3) | C21—C16—C17 | 115.9 (4) |
N2—C4—C3 | 127.1 (3) | C21—C16—C15 | 124.4 (3) |
N2—C4—S1 | 122.8 (3) | C17—C16—C15 | 119.6 (4) |
C3—C4—S1 | 110.1 (3) | C18—C17—C16 | 122.5 (4) |
C1—C5—H5A | 109.5 | C18—C17—H17 | 118.8 |
C1—C5—H5B | 109.5 | C16—C17—H17 | 118.8 |
H5A—C5—H5B | 109.5 | C17—C18—C19 | 121.2 (4) |
C1—C5—H5C | 109.5 | C17—C18—H18 | 119.4 |
H5A—C5—H5C | 109.5 | C19—C18—H18 | 119.4 |
H5B—C5—H5C | 109.5 | N3—C19—C18 | 121.6 (4) |
C2—C6—H6A | 109.5 | N3—C19—C20 | 122.0 (4) |
C2—C6—H6B | 109.5 | C18—C19—C20 | 116.4 (4) |
H6A—C6—H6B | 109.5 | C21—C20—C19 | 121.2 (4) |
C2—C6—H6C | 109.5 | C21—C20—H20 | 119.4 |
H6A—C6—H6C | 109.5 | C19—C20—H20 | 119.4 |
H6B—C6—H6C | 109.5 | C20—C21—C16 | 122.7 (4) |
O1—C7—N1 | 122.1 (4) | C20—C21—H21 | 118.6 |
O1—C7—C3 | 121.8 (4) | C16—C21—H21 | 118.6 |
N1—C7—C3 | 116.1 (3) | N3—C22—H22A | 109.5 |
C9—C8—C13 | 120.0 (4) | N3—C22—H22B | 109.5 |
C9—C8—N1 | 119.3 (4) | H22A—C22—H22B | 109.5 |
C13—C8—N1 | 120.7 (4) | N3—C22—H22C | 109.5 |
C10—C9—C8 | 119.2 (4) | H22A—C22—H22C | 109.5 |
C10—C9—C14 | 119.6 (4) | H22B—C22—H22C | 109.5 |
C8—C9—C14 | 121.2 (3) | N3—C23—H23A | 109.5 |
C9—C10—C11 | 120.7 (4) | N3—C23—H23B | 109.5 |
C9—C10—H10 | 119.6 | H23A—C23—H23B | 109.5 |
C11—C10—H10 | 119.6 | N3—C23—H23C | 109.5 |
C12—C11—C10 | 120.0 (4) | H23A—C23—H23C | 109.5 |
C12—C11—H11 | 120.0 | H23B—C23—H23C | 109.5 |
C4—S1—C1—C2 | −1.2 (3) | N1—C8—C9—C10 | −178.6 (4) |
C4—S1—C1—C5 | 177.5 (3) | C13—C8—C9—C14 | −177.8 (4) |
C5—C1—C2—C3 | −178.3 (4) | N1—C8—C9—C14 | 2.8 (5) |
S1—C1—C2—C3 | 0.3 (4) | C8—C9—C10—C11 | −0.4 (6) |
C5—C1—C2—C6 | −2.2 (6) | C14—C9—C10—C11 | 178.2 (4) |
S1—C1—C2—C6 | 176.3 (3) | C9—C10—C11—C12 | −0.6 (6) |
C1—C2—C3—C4 | 1.2 (4) | C10—C11—C12—C13 | 1.2 (6) |
C6—C2—C3—C4 | −174.8 (3) | C11—C12—C13—C8 | −0.8 (6) |
C1—C2—C3—C7 | −177.2 (3) | C9—C8—C13—C12 | −0.2 (6) |
C6—C2—C3—C7 | 6.9 (6) | N1—C8—C13—C12 | 179.2 (4) |
C15—N2—C4—C3 | 179.5 (3) | C4—N2—C15—C16 | 178.2 (3) |
C15—N2—C4—S1 | −1.8 (5) | N2—C15—C16—C21 | 1.7 (6) |
C2—C3—C4—N2 | 176.8 (3) | N2—C15—C16—C17 | −179.4 (4) |
C7—C3—C4—N2 | −4.9 (6) | C21—C16—C17—C18 | −0.8 (6) |
C2—C3—C4—S1 | −2.0 (4) | C15—C16—C17—C18 | −179.8 (4) |
C7—C3—C4—S1 | 176.3 (3) | C16—C17—C18—C19 | 1.8 (6) |
C1—S1—C4—N2 | −177.0 (3) | C23—N3—C19—C18 | 1.3 (5) |
C1—S1—C4—C3 | 1.8 (3) | C22—N3—C19—C18 | 179.6 (3) |
C8—N1—C7—O1 | −1.0 (6) | C23—N3—C19—C20 | −179.4 (3) |
C8—N1—C7—C3 | 177.3 (4) | C22—N3—C19—C20 | −1.1 (5) |
C4—C3—C7—O1 | −166.1 (4) | C17—C18—C19—N3 | 177.0 (4) |
C2—C3—C7—O1 | 12.1 (5) | C17—C18—C19—C20 | −2.4 (5) |
C4—C3—C7—N1 | 15.6 (5) | N3—C19—C20—C21 | −177.3 (4) |
C2—C3—C7—N1 | −166.3 (3) | C18—C19—C20—C21 | 2.1 (5) |
C7—N1—C8—C9 | −137.4 (4) | C19—C20—C21—C16 | −1.2 (6) |
C7—N1—C8—C13 | 43.2 (6) | C17—C16—C21—C20 | 0.5 (6) |
C13—C8—C9—C10 | 0.8 (5) | C15—C16—C21—C20 | 179.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···N2 | 0.77 (3) | 2.12 (3) | 2.766 (5) | 143 (3) |
C25H27N3OS | F(000) = 1776 |
Mr = 417.57 | Dx = 1.283 Mg m−3 |
Monoclinic, P21/n | Melting point: 497 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 8.016 (2) Å | Cell parameters from 839 reflections |
b = 21.255 (6) Å | θ = 2.6–21.4° |
c = 25.651 (7) Å | µ = 0.17 mm−1 |
β = 98.378 (5)° | T = 293 K |
V = 4324 (2) Å3 | Prism, yellow |
Z = 8 | 0.40 × 0.35 × 0.30 mm |
Bruker SMART CCD area-detector diffractometer | 8756 independent reflections |
Radiation source: fine-focus sealed tube | 6163 reflections with I > \2s(I) |
Graphite monochromator | Rint = 0.034 |
ϕ and ω scans | θmax = 26.4°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −10→10 |
Tmin = 0.925, Tmax = 0.950 | k = −24→26 |
33520 measured reflections | l = −31→31 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.165 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.067P)2 + 2.0342P] where P = (Fo2 + 2Fc2)/3 |
8756 reflections | (Δ/σ)max = 0.002 |
555 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C25H27N3OS | V = 4324 (2) Å3 |
Mr = 417.57 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.016 (2) Å | µ = 0.17 mm−1 |
b = 21.255 (6) Å | T = 293 K |
c = 25.651 (7) Å | 0.40 × 0.35 × 0.30 mm |
β = 98.378 (5)° |
Bruker SMART CCD area-detector diffractometer | 8756 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | 6163 reflections with I > \2s(I) |
Tmin = 0.925, Tmax = 0.950 | Rint = 0.034 |
33520 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.165 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.49 e Å−3 |
8756 reflections | Δρmin = −0.24 e Å−3 |
555 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 | ||
S1 | 0.49293 (9) | −0.01762 (3) | 0.19855 (3) | 0.05455 (19) | |
S2 | 0.73415 (10) | 0.48537 (3) | 0.03428 (3) | 0.0618 (2) | |
O1 | 0.5845 (3) | 0.20764 (9) | 0.16755 (8) | 0.0805 (7) | |
O2 | 0.6664 (3) | 0.71180 (9) | 0.06871 (8) | 0.0754 (6) | |
N1 | 0.6575 (3) | 0.14875 (11) | 0.10127 (9) | 0.0543 (6) | |
N2 | 0.6188 (3) | 0.01925 (10) | 0.10899 (8) | 0.0497 (5) | |
N3 | 0.8363 (3) | −0.13307 (10) | −0.08932 (9) | 0.0612 (6) | |
N4 | 0.6033 (3) | 0.65224 (11) | 0.13611 (9) | 0.0569 (6) | |
N5 | 0.6625 (3) | 0.52438 (10) | 0.13115 (9) | 0.0530 (5) | |
N6 | 0.5321 (3) | 0.37217 (10) | 0.34057 (9) | 0.0642 (6) | |
C1 | 0.4512 (3) | 0.04110 (12) | 0.24113 (10) | 0.0496 (6) | |
C2 | 0.4868 (3) | 0.09932 (11) | 0.22411 (10) | 0.0474 (6) | |
C3 | 0.5520 (3) | 0.09745 (11) | 0.17417 (9) | 0.0461 (6) | |
C4 | 0.5618 (3) | 0.03659 (12) | 0.15547 (10) | 0.0471 (6) | |
C5 | 0.3801 (4) | 0.02584 (13) | 0.29086 (11) | 0.0602 (7) | |
H5A | 0.4692 | 0.0107 | 0.3176 | 0.072* | |
H5B | 0.2957 | −0.0070 | 0.2839 | 0.072* | |
C6 | 0.4516 (4) | 0.15717 (12) | 0.25497 (11) | 0.0574 (7) | |
H6A | 0.3607 | 0.1808 | 0.2349 | 0.069* | |
H6B | 0.5511 | 0.1837 | 0.2598 | 0.069* | |
C7 | 0.5993 (3) | 0.15607 (12) | 0.14775 (10) | 0.0491 (6) | |
C8 | 0.7053 (3) | 0.19525 (11) | 0.06719 (10) | 0.0478 (6) | |
C9 | 0.7590 (4) | 0.17645 (13) | 0.02096 (11) | 0.0641 (8) | |
H9 | 0.7642 | 0.1337 | 0.0135 | 0.077* | |
C10 | 0.8053 (4) | 0.21969 (13) | −0.01445 (11) | 0.0665 (8) | |
H10 | 0.8408 | 0.2053 | −0.0453 | 0.080* | |
C11 | 0.8003 (3) | 0.28335 (13) | −0.00546 (11) | 0.0552 (6) | |
C12 | 0.7488 (4) | 0.30153 (13) | 0.04093 (12) | 0.0691 (8) | |
H12 | 0.7455 | 0.3443 | 0.0485 | 0.083* | |
C13 | 0.7015 (4) | 0.25907 (13) | 0.07709 (12) | 0.0661 (8) | |
H13 | 0.6673 | 0.2736 | 0.1080 | 0.079* | |
C14 | 0.8436 (4) | 0.33057 (15) | −0.04576 (12) | 0.0751 (9) | |
H14A | 0.7440 | 0.3404 | −0.0699 | 0.113* | |
H14B | 0.9271 | 0.3129 | −0.0648 | 0.113* | |
H14C | 0.8871 | 0.3682 | −0.0281 | 0.113* | |
C15 | 0.6116 (3) | −0.03865 (12) | 0.09393 (11) | 0.0548 (6) | |
H15 | 0.5675 | −0.0678 | 0.1153 | 0.066* | |
C16 | 0.6668 (3) | −0.06147 (12) | 0.04646 (10) | 0.0504 (6) | |
C17 | 0.6627 (4) | −0.12578 (12) | 0.03521 (11) | 0.0578 (7) | |
H17 | 0.6208 | −0.1532 | 0.0584 | 0.069* | |
C18 | 0.7183 (3) | −0.15002 (12) | −0.00884 (11) | 0.0574 (7) | |
H18 | 0.7133 | −0.1932 | −0.0149 | 0.069* | |
C19 | 0.7827 (3) | −0.11019 (12) | −0.04496 (10) | 0.0504 (6) | |
C20 | 0.7884 (4) | −0.04532 (12) | −0.03343 (10) | 0.0571 (7) | |
H20 | 0.8313 | −0.0177 | −0.0563 | 0.069* | |
C21 | 0.7323 (4) | −0.02214 (12) | 0.01065 (11) | 0.0570 (7) | |
H21 | 0.7377 | 0.0209 | 0.0170 | 0.068* | |
C22 | 0.9040 (4) | −0.09195 (14) | −0.12622 (11) | 0.0679 (8) | |
H22A | 0.8203 | −0.0614 | −0.1397 | 0.102* | |
H22B | 0.9344 | −0.1164 | −0.1548 | 0.102* | |
H22C | 1.0020 | −0.0708 | −0.1086 | 0.102* | |
C23 | 0.8283 (4) | −0.19981 (13) | −0.10115 (12) | 0.0713 (8) | |
H23A | 0.9064 | −0.2220 | −0.0757 | 0.107* | |
H23B | 0.8570 | −0.2067 | −0.1358 | 0.107* | |
H23C | 0.7161 | −0.2149 | −0.0998 | 0.107* | |
C24 | 0.3008 (5) | 0.08503 (16) | 0.31048 (15) | 0.0916 (11) | |
H24A | 0.1918 | 0.0919 | 0.2893 | 0.110* | |
H24B | 0.2822 | 0.0784 | 0.3466 | 0.110* | |
C25 | 0.4036 (5) | 0.14124 (17) | 0.30827 (14) | 0.0885 (11) | |
H25A | 0.5064 | 0.1361 | 0.3330 | 0.106* | |
H25B | 0.3430 | 0.1768 | 0.3201 | 0.106* | |
C26 | 0.7441 (3) | 0.54270 (12) | −0.01281 (10) | 0.0527 (6) | |
C27 | 0.7157 (3) | 0.60131 (11) | 0.00552 (10) | 0.0486 (6) | |
C28 | 0.6853 (3) | 0.60080 (11) | 0.05956 (10) | 0.0483 (6) | |
C29 | 0.6913 (3) | 0.54086 (12) | 0.08058 (10) | 0.0493 (6) | |
C30 | 0.7750 (4) | 0.52575 (13) | −0.06734 (11) | 0.0637 (7) | |
H30A | 0.6789 | 0.5028 | −0.0853 | 0.076* | |
H30B | 0.8734 | 0.4988 | −0.0653 | 0.076* | |
C31 | 0.7106 (4) | 0.65737 (12) | −0.03070 (10) | 0.0581 (7) | |
H31A | 0.8153 | 0.6807 | −0.0230 | 0.070* | |
H31B | 0.6191 | 0.6850 | −0.0246 | 0.070* | |
C32 | 0.6515 (3) | 0.66003 (12) | 0.08804 (10) | 0.0516 (6) | |
C33 | 0.5562 (3) | 0.69912 (11) | 0.16980 (10) | 0.0498 (6) | |
C34 | 0.5828 (3) | 0.68879 (13) | 0.22380 (11) | 0.0574 (7) | |
H34 | 0.6385 | 0.6525 | 0.2371 | 0.069* | |
C35 | 0.5278 (4) | 0.73148 (14) | 0.25817 (12) | 0.0633 (7) | |
H35 | 0.5479 | 0.7235 | 0.2942 | 0.076* | |
C36 | 0.4435 (4) | 0.78603 (14) | 0.24023 (13) | 0.0647 (8) | |
C37 | 0.4225 (4) | 0.79665 (13) | 0.18636 (13) | 0.0665 (8) | |
H37 | 0.3700 | 0.8336 | 0.1733 | 0.080* | |
C38 | 0.4762 (3) | 0.75476 (13) | 0.15124 (11) | 0.0590 (7) | |
H38 | 0.4592 | 0.7636 | 0.1153 | 0.071* | |
C39 | 0.3793 (5) | 0.83195 (17) | 0.27746 (15) | 0.0955 (12) | |
H39A | 0.3189 | 0.8652 | 0.2576 | 0.143* | |
H39B | 0.4728 | 0.8493 | 0.3006 | 0.143* | |
H39C | 0.3053 | 0.8106 | 0.2978 | 0.143* | |
C40 | 0.6831 (3) | 0.46715 (12) | 0.14748 (11) | 0.0545 (6) | |
H40 | 0.7247 | 0.4383 | 0.1253 | 0.065* | |
C41 | 0.6464 (3) | 0.44458 (12) | 0.19742 (10) | 0.0526 (6) | |
C42 | 0.5840 (3) | 0.48311 (12) | 0.23438 (11) | 0.0563 (7) | |
H42 | 0.5684 | 0.5258 | 0.2271 | 0.068* | |
C43 | 0.5455 (3) | 0.45996 (12) | 0.28058 (11) | 0.0576 (7) | |
H43 | 0.5035 | 0.4870 | 0.3040 | 0.069* | |
C44 | 0.5680 (3) | 0.39541 (12) | 0.29384 (11) | 0.0528 (6) | |
C45 | 0.6305 (4) | 0.35677 (12) | 0.25661 (11) | 0.0609 (7) | |
H45 | 0.6469 | 0.3141 | 0.2636 | 0.073* | |
C46 | 0.6678 (4) | 0.38104 (12) | 0.21003 (11) | 0.0600 (7) | |
H46 | 0.7086 | 0.3542 | 0.1862 | 0.072* | |
C47 | 0.4505 (4) | 0.41090 (14) | 0.37606 (12) | 0.0683 (8) | |
H47A | 0.5207 | 0.4465 | 0.3871 | 0.102* | |
H47B | 0.4331 | 0.3866 | 0.4063 | 0.102* | |
H47C | 0.3438 | 0.4253 | 0.3582 | 0.102* | |
C48 | 0.5539 (4) | 0.30584 (14) | 0.35324 (13) | 0.0790 (9) | |
H48A | 0.4697 | 0.2819 | 0.3313 | 0.119* | |
H48B | 0.5424 | 0.2993 | 0.3896 | 0.119* | |
H48C | 0.6639 | 0.2925 | 0.3472 | 0.119* | |
C49 | 0.6853 (5) | 0.63665 (15) | −0.08820 (12) | 0.0804 (10) | |
H49A | 0.5701 | 0.6224 | −0.0979 | 0.096* | |
H49B | 0.7025 | 0.6725 | −0.1102 | 0.096* | |
C50 | 0.8031 (5) | 0.58504 (15) | −0.09847 (13) | 0.0845 (10) | |
H50A | 0.9185 | 0.5992 | −0.0888 | 0.101* | |
H50B | 0.7863 | 0.5753 | −0.1358 | 0.101* | |
H4N | 0.604 (4) | 0.6164 (15) | 0.1484 (12) | 0.072 (10)* | |
H1N | 0.663 (4) | 0.1110 (15) | 0.0894 (11) | 0.069 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0662 (4) | 0.0421 (4) | 0.0574 (4) | 0.0004 (3) | 0.0161 (3) | 0.0057 (3) |
S2 | 0.0821 (5) | 0.0381 (4) | 0.0686 (5) | 0.0041 (3) | 0.0221 (4) | −0.0001 (3) |
O1 | 0.138 (2) | 0.0450 (12) | 0.0677 (13) | −0.0149 (12) | 0.0447 (13) | −0.0060 (10) |
O2 | 0.1304 (19) | 0.0373 (11) | 0.0638 (12) | −0.0113 (11) | 0.0324 (12) | −0.0025 (9) |
N1 | 0.0729 (15) | 0.0364 (12) | 0.0580 (14) | 0.0003 (10) | 0.0240 (11) | 0.0018 (10) |
N2 | 0.0579 (12) | 0.0419 (12) | 0.0500 (12) | 0.0028 (9) | 0.0099 (10) | −0.0002 (9) |
N3 | 0.0882 (17) | 0.0421 (13) | 0.0555 (13) | 0.0041 (11) | 0.0177 (12) | −0.0008 (10) |
N4 | 0.0764 (16) | 0.0394 (13) | 0.0575 (14) | 0.0018 (11) | 0.0188 (11) | 0.0022 (11) |
N5 | 0.0591 (13) | 0.0421 (12) | 0.0584 (13) | −0.0013 (9) | 0.0109 (10) | 0.0041 (10) |
N6 | 0.0878 (17) | 0.0424 (13) | 0.0656 (15) | 0.0108 (11) | 0.0217 (13) | 0.0085 (11) |
C1 | 0.0494 (13) | 0.0500 (15) | 0.0502 (14) | 0.0009 (11) | 0.0102 (11) | 0.0041 (12) |
C2 | 0.0459 (13) | 0.0449 (14) | 0.0513 (14) | −0.0011 (10) | 0.0075 (11) | 0.0020 (11) |
C3 | 0.0473 (13) | 0.0433 (14) | 0.0481 (14) | −0.0002 (10) | 0.0081 (11) | 0.0014 (11) |
C4 | 0.0473 (13) | 0.0440 (14) | 0.0503 (14) | 0.0012 (10) | 0.0085 (11) | 0.0055 (11) |
C5 | 0.0653 (17) | 0.0604 (18) | 0.0573 (16) | −0.0009 (13) | 0.0171 (13) | 0.0096 (13) |
C6 | 0.0664 (17) | 0.0485 (16) | 0.0606 (16) | −0.0039 (12) | 0.0197 (13) | −0.0052 (13) |
C7 | 0.0561 (15) | 0.0429 (14) | 0.0492 (14) | −0.0023 (11) | 0.0106 (11) | 0.0006 (11) |
C8 | 0.0529 (14) | 0.0406 (14) | 0.0514 (14) | 0.0007 (10) | 0.0126 (11) | 0.0061 (11) |
C9 | 0.098 (2) | 0.0403 (15) | 0.0575 (17) | 0.0006 (14) | 0.0241 (15) | −0.0009 (13) |
C10 | 0.097 (2) | 0.0537 (18) | 0.0539 (16) | −0.0025 (15) | 0.0277 (15) | −0.0015 (13) |
C11 | 0.0593 (16) | 0.0530 (16) | 0.0532 (15) | −0.0052 (12) | 0.0072 (12) | 0.0076 (12) |
C12 | 0.098 (2) | 0.0375 (15) | 0.078 (2) | 0.0002 (14) | 0.0353 (17) | 0.0036 (14) |
C13 | 0.091 (2) | 0.0448 (16) | 0.0703 (19) | 0.0036 (14) | 0.0384 (16) | 0.0010 (14) |
C14 | 0.096 (2) | 0.064 (2) | 0.0659 (19) | −0.0155 (17) | 0.0165 (17) | 0.0155 (15) |
C15 | 0.0610 (16) | 0.0449 (15) | 0.0602 (16) | 0.0009 (12) | 0.0143 (13) | 0.0046 (12) |
C16 | 0.0567 (15) | 0.0393 (13) | 0.0555 (15) | 0.0015 (11) | 0.0091 (12) | −0.0003 (11) |
C17 | 0.0710 (17) | 0.0422 (15) | 0.0628 (17) | −0.0042 (12) | 0.0188 (14) | 0.0023 (12) |
C18 | 0.0735 (18) | 0.0347 (13) | 0.0646 (17) | −0.0029 (12) | 0.0125 (14) | −0.0048 (12) |
C19 | 0.0578 (15) | 0.0395 (13) | 0.0524 (15) | 0.0040 (11) | 0.0036 (12) | 0.0007 (11) |
C20 | 0.0801 (19) | 0.0379 (14) | 0.0553 (16) | −0.0016 (12) | 0.0163 (14) | 0.0046 (12) |
C21 | 0.0804 (19) | 0.0321 (13) | 0.0594 (16) | 0.0002 (12) | 0.0128 (14) | −0.0016 (12) |
C22 | 0.085 (2) | 0.0618 (19) | 0.0601 (18) | 0.0041 (15) | 0.0207 (15) | −0.0013 (14) |
C23 | 0.095 (2) | 0.0481 (17) | 0.0716 (19) | 0.0058 (15) | 0.0158 (17) | −0.0126 (14) |
C24 | 0.125 (3) | 0.072 (2) | 0.090 (3) | −0.008 (2) | 0.058 (2) | −0.0021 (19) |
C25 | 0.124 (3) | 0.071 (2) | 0.082 (2) | −0.011 (2) | 0.056 (2) | −0.0100 (18) |
C26 | 0.0567 (15) | 0.0451 (15) | 0.0577 (16) | −0.0019 (11) | 0.0131 (12) | −0.0023 (12) |
C27 | 0.0508 (14) | 0.0425 (14) | 0.0523 (15) | −0.0074 (11) | 0.0065 (11) | −0.0033 (11) |
C28 | 0.0512 (14) | 0.0395 (14) | 0.0540 (15) | −0.0056 (10) | 0.0071 (11) | −0.0025 (11) |
C29 | 0.0528 (14) | 0.0400 (13) | 0.0558 (15) | −0.0030 (11) | 0.0097 (11) | −0.0021 (11) |
C30 | 0.0791 (19) | 0.0526 (17) | 0.0625 (17) | −0.0007 (14) | 0.0203 (15) | −0.0076 (13) |
C31 | 0.0786 (19) | 0.0442 (15) | 0.0517 (15) | −0.0060 (13) | 0.0103 (13) | −0.0013 (12) |
C32 | 0.0596 (16) | 0.0404 (15) | 0.0544 (15) | −0.0053 (11) | 0.0075 (12) | −0.0039 (11) |
C33 | 0.0554 (14) | 0.0376 (13) | 0.0579 (16) | −0.0052 (11) | 0.0135 (12) | −0.0023 (11) |
C34 | 0.0639 (16) | 0.0454 (15) | 0.0648 (18) | 0.0011 (12) | 0.0160 (13) | 0.0041 (13) |
C35 | 0.0748 (19) | 0.0600 (18) | 0.0584 (17) | −0.0082 (14) | 0.0205 (14) | −0.0056 (14) |
C36 | 0.0690 (18) | 0.0504 (17) | 0.079 (2) | −0.0077 (14) | 0.0270 (15) | −0.0143 (15) |
C37 | 0.0699 (18) | 0.0448 (16) | 0.086 (2) | 0.0067 (13) | 0.0144 (15) | −0.0019 (15) |
C38 | 0.0683 (17) | 0.0473 (15) | 0.0611 (17) | 0.0011 (13) | 0.0088 (13) | 0.0005 (13) |
C39 | 0.114 (3) | 0.073 (2) | 0.108 (3) | 0.005 (2) | 0.048 (2) | −0.024 (2) |
C40 | 0.0596 (15) | 0.0444 (15) | 0.0591 (16) | 0.0002 (12) | 0.0068 (12) | −0.0015 (12) |
C41 | 0.0563 (15) | 0.0427 (14) | 0.0574 (16) | 0.0012 (11) | 0.0036 (12) | 0.0033 (12) |
C42 | 0.0660 (16) | 0.0356 (14) | 0.0682 (17) | 0.0069 (12) | 0.0123 (13) | 0.0090 (12) |
C43 | 0.0682 (17) | 0.0412 (14) | 0.0651 (17) | 0.0087 (12) | 0.0158 (14) | 0.0001 (13) |
C44 | 0.0559 (15) | 0.0429 (14) | 0.0590 (16) | 0.0031 (11) | 0.0061 (12) | 0.0053 (12) |
C45 | 0.0800 (19) | 0.0361 (14) | 0.0664 (18) | 0.0081 (13) | 0.0100 (14) | 0.0062 (13) |
C46 | 0.0804 (19) | 0.0403 (14) | 0.0597 (17) | 0.0068 (13) | 0.0110 (14) | 0.0009 (12) |
C47 | 0.077 (2) | 0.0629 (19) | 0.0667 (19) | 0.0073 (15) | 0.0178 (15) | 0.0030 (15) |
C48 | 0.101 (2) | 0.0553 (19) | 0.086 (2) | 0.0148 (17) | 0.0297 (19) | 0.0219 (16) |
C49 | 0.129 (3) | 0.0529 (18) | 0.0586 (18) | −0.0031 (18) | 0.0129 (18) | 0.0000 (14) |
C50 | 0.129 (3) | 0.065 (2) | 0.067 (2) | 0.002 (2) | 0.039 (2) | 0.0001 (16) |
S1—C1 | 1.723 (3) | C22—H22A | 0.9600 |
S1—C4 | 1.741 (3) | C22—H22B | 0.9600 |
S2—C26 | 1.726 (3) | C22—H22C | 0.9600 |
S2—C29 | 1.743 (3) | C23—H23A | 0.9600 |
O1—C7 | 1.221 (3) | C23—H23B | 0.9600 |
O2—C32 | 1.220 (3) | C23—H23C | 0.9600 |
N1—C7 | 1.351 (3) | C24—C25 | 1.457 (5) |
N1—C8 | 1.409 (3) | C24—H24A | 0.9700 |
N1—H1N | 0.86 (3) | C24—H24B | 0.9700 |
N2—C15 | 1.289 (3) | C25—H25A | 0.9700 |
N2—C4 | 1.387 (3) | C25—H25B | 0.9700 |
N3—C19 | 1.363 (3) | C26—C27 | 1.363 (3) |
N3—C22 | 1.450 (3) | C26—C30 | 1.499 (4) |
N3—C23 | 1.450 (4) | C27—C28 | 1.442 (4) |
N4—C32 | 1.355 (3) | C27—C31 | 1.508 (3) |
N4—C33 | 1.406 (3) | C28—C29 | 1.381 (3) |
N4—H4N | 0.82 (3) | C28—C32 | 1.500 (3) |
N5—C40 | 1.289 (3) | C30—C50 | 1.526 (4) |
N5—C29 | 1.395 (3) | C30—H30A | 0.9700 |
N6—C44 | 1.365 (3) | C30—H30B | 0.9700 |
N6—C48 | 1.452 (4) | C31—C49 | 1.524 (4) |
N6—C47 | 1.452 (4) | C31—H31A | 0.9700 |
C1—C2 | 1.356 (3) | C31—H31B | 0.9700 |
C1—C5 | 1.506 (4) | C33—C34 | 1.388 (4) |
C2—C3 | 1.453 (3) | C33—C38 | 1.396 (4) |
C2—C6 | 1.511 (3) | C34—C35 | 1.381 (4) |
C3—C4 | 1.386 (3) | C34—H34 | 0.9300 |
C3—C7 | 1.494 (3) | C35—C36 | 1.387 (4) |
C5—C24 | 1.527 (4) | C35—H35 | 0.9300 |
C5—H5A | 0.9700 | C36—C37 | 1.386 (4) |
C5—H5B | 0.9700 | C36—C39 | 1.508 (4) |
C6—C25 | 1.511 (4) | C37—C38 | 1.379 (4) |
C6—H6A | 0.9700 | C37—H37 | 0.9300 |
C6—H6B | 0.9700 | C38—H38 | 0.9300 |
C8—C9 | 1.379 (4) | C39—H39A | 0.9600 |
C8—C13 | 1.381 (4) | C39—H39B | 0.9600 |
C9—C10 | 1.380 (4) | C39—H39C | 0.9600 |
C9—H9 | 0.9300 | C40—C41 | 1.438 (4) |
C10—C11 | 1.374 (4) | C40—H40 | 0.9300 |
C10—H10 | 0.9300 | C41—C46 | 1.393 (4) |
C11—C12 | 1.371 (4) | C41—C42 | 1.399 (4) |
C11—C14 | 1.517 (4) | C42—C43 | 1.360 (4) |
C12—C13 | 1.386 (4) | C42—H42 | 0.9300 |
C12—H12 | 0.9300 | C43—C44 | 1.419 (4) |
C13—H13 | 0.9300 | C43—H43 | 0.9300 |
C14—H14A | 0.9600 | C44—C45 | 1.406 (4) |
C14—H14B | 0.9600 | C45—C46 | 1.374 (4) |
C14—H14C | 0.9600 | C45—H45 | 0.9300 |
C15—C16 | 1.439 (4) | C46—H46 | 0.9300 |
C15—H15 | 0.9300 | C47—H47A | 0.9600 |
C16—C17 | 1.397 (4) | C47—H47B | 0.9600 |
C16—C21 | 1.399 (4) | C47—H47C | 0.9600 |
C17—C18 | 1.374 (4) | C48—H48A | 0.9600 |
C17—H17 | 0.9300 | C48—H48B | 0.9600 |
C18—C19 | 1.407 (4) | C48—H48C | 0.9600 |
C18—H18 | 0.9300 | C49—C50 | 1.495 (5) |
C19—C20 | 1.410 (4) | C49—H49A | 0.9700 |
C20—C21 | 1.369 (4) | C49—H49B | 0.9700 |
C20—H20 | 0.9300 | C50—H50A | 0.9700 |
C21—H21 | 0.9300 | C50—H50B | 0.9700 |
C1—S1—C4 | 91.82 (12) | C5—C24—H24B | 108.9 |
C26—S2—C29 | 91.89 (13) | H24A—C24—H24B | 107.7 |
C7—N1—C8 | 128.8 (2) | C24—C25—C6 | 116.0 (3) |
C7—N1—H1N | 117 (2) | C24—C25—H25A | 108.3 |
C8—N1—H1N | 114 (2) | C6—C25—H25A | 108.3 |
C15—N2—C4 | 120.4 (2) | C24—C25—H25B | 108.3 |
C19—N3—C22 | 121.6 (2) | C6—C25—H25B | 108.3 |
C19—N3—C23 | 120.9 (2) | H25A—C25—H25B | 107.4 |
C22—N3—C23 | 117.5 (2) | C27—C26—C30 | 126.9 (2) |
C32—N4—C33 | 127.6 (2) | C27—C26—S2 | 112.1 (2) |
C32—N4—H4N | 118 (2) | C30—C26—S2 | 120.93 (19) |
C33—N4—H4N | 114 (2) | C26—C27—C28 | 112.6 (2) |
C40—N5—C29 | 120.6 (2) | C26—C27—C31 | 120.0 (2) |
C44—N6—C48 | 120.9 (2) | C28—C27—C31 | 127.2 (2) |
C44—N6—C47 | 121.1 (2) | C29—C28—C27 | 112.4 (2) |
C48—N6—C47 | 117.4 (2) | C29—C28—C32 | 125.6 (2) |
C2—C1—C5 | 126.3 (2) | C27—C28—C32 | 122.0 (2) |
C2—C1—S1 | 112.79 (19) | C28—C29—N5 | 126.4 (2) |
C5—C1—S1 | 120.88 (19) | C28—C29—S2 | 110.94 (19) |
C1—C2—C3 | 112.2 (2) | N5—C29—S2 | 122.64 (19) |
C1—C2—C6 | 120.6 (2) | C26—C30—C50 | 110.3 (2) |
C3—C2—C6 | 127.1 (2) | C26—C30—H30A | 109.6 |
C4—C3—C2 | 112.1 (2) | C50—C30—H30A | 109.6 |
C4—C3—C7 | 126.2 (2) | C26—C30—H30B | 109.6 |
C2—C3—C7 | 121.7 (2) | C50—C30—H30B | 109.6 |
C3—C4—N2 | 126.0 (2) | H30A—C30—H30B | 108.1 |
C3—C4—S1 | 111.02 (19) | C27—C31—C49 | 110.8 (2) |
N2—C4—S1 | 122.97 (18) | C27—C31—H31A | 109.5 |
C1—C5—C24 | 109.2 (2) | C49—C31—H31A | 109.5 |
C1—C5—H5A | 109.8 | C27—C31—H31B | 109.5 |
C24—C5—H5A | 109.8 | C49—C31—H31B | 109.5 |
C1—C5—H5B | 109.8 | H31A—C31—H31B | 108.1 |
C24—C5—H5B | 109.8 | O2—C32—N4 | 122.6 (2) |
H5A—C5—H5B | 108.3 | O2—C32—C28 | 121.6 (2) |
C2—C6—C25 | 112.5 (2) | N4—C32—C28 | 115.9 (2) |
C2—C6—H6A | 109.1 | C34—C33—C38 | 118.1 (2) |
C25—C6—H6A | 109.1 | C34—C33—N4 | 119.0 (2) |
C2—C6—H6B | 109.1 | C38—C33—N4 | 122.8 (2) |
C25—C6—H6B | 109.1 | C35—C34—C33 | 121.1 (3) |
H6A—C6—H6B | 107.8 | C35—C34—H34 | 119.5 |
O1—C7—N1 | 122.5 (2) | C33—C34—H34 | 119.5 |
O1—C7—C3 | 120.9 (2) | C34—C35—C36 | 121.5 (3) |
N1—C7—C3 | 116.6 (2) | C34—C35—H35 | 119.2 |
C9—C8—C13 | 117.4 (2) | C36—C35—H35 | 119.2 |
C9—C8—N1 | 118.5 (2) | C37—C36—C35 | 116.7 (3) |
C13—C8—N1 | 124.0 (2) | C37—C36—C39 | 121.5 (3) |
C8—C9—C10 | 121.4 (3) | C35—C36—C39 | 121.7 (3) |
C8—C9—H9 | 119.3 | C38—C37—C36 | 122.8 (3) |
C10—C9—H9 | 119.3 | C38—C37—H37 | 118.6 |
C11—C10—C9 | 121.9 (3) | C36—C37—H37 | 118.6 |
C11—C10—H10 | 119.1 | C37—C38—C33 | 119.7 (3) |
C9—C10—H10 | 119.1 | C37—C38—H38 | 120.1 |
C12—C11—C10 | 116.3 (2) | C33—C38—H38 | 120.1 |
C12—C11—C14 | 122.2 (3) | C36—C39—H39A | 109.5 |
C10—C11—C14 | 121.5 (3) | C36—C39—H39B | 109.5 |
C11—C12—C13 | 122.9 (3) | H39A—C39—H39B | 109.5 |
C11—C12—H12 | 118.5 | C36—C39—H39C | 109.5 |
C13—C12—H12 | 118.5 | H39A—C39—H39C | 109.5 |
C8—C13—C12 | 120.1 (3) | H39B—C39—H39C | 109.5 |
C8—C13—H13 | 120.0 | N5—C40—C41 | 124.8 (3) |
C12—C13—H13 | 120.0 | N5—C40—H40 | 117.6 |
C11—C14—H14A | 109.5 | C41—C40—H40 | 117.6 |
C11—C14—H14B | 109.5 | C46—C41—C42 | 117.0 (2) |
H14A—C14—H14B | 109.5 | C46—C41—C40 | 119.7 (3) |
C11—C14—H14C | 109.5 | C42—C41—C40 | 123.2 (2) |
H14A—C14—H14C | 109.5 | C43—C42—C41 | 121.8 (2) |
H14B—C14—H14C | 109.5 | C43—C42—H42 | 119.1 |
N2—C15—C16 | 124.7 (2) | C41—C42—H42 | 119.1 |
N2—C15—H15 | 117.6 | C42—C43—C44 | 121.5 (3) |
C16—C15—H15 | 117.6 | C42—C43—H43 | 119.3 |
C17—C16—C21 | 116.7 (2) | C44—C43—H43 | 119.3 |
C17—C16—C15 | 120.2 (2) | N6—C44—C45 | 121.8 (2) |
C21—C16—C15 | 123.0 (2) | N6—C44—C43 | 121.7 (2) |
C18—C17—C16 | 122.4 (3) | C45—C44—C43 | 116.6 (2) |
C18—C17—H17 | 118.8 | C46—C45—C44 | 121.0 (2) |
C16—C17—H17 | 118.8 | C46—C45—H45 | 119.5 |
C17—C18—C19 | 120.7 (2) | C44—C45—H45 | 119.5 |
C17—C18—H18 | 119.7 | C45—C46—C41 | 122.1 (3) |
C19—C18—H18 | 119.7 | C45—C46—H46 | 119.0 |
N3—C19—C18 | 121.7 (2) | C41—C46—H46 | 119.0 |
N3—C19—C20 | 121.3 (2) | N6—C47—H47A | 109.5 |
C18—C19—C20 | 117.0 (2) | N6—C47—H47B | 109.5 |
C21—C20—C19 | 121.4 (2) | H47A—C47—H47B | 109.5 |
C21—C20—H20 | 119.3 | N6—C47—H47C | 109.5 |
C19—C20—H20 | 119.3 | H47A—C47—H47C | 109.5 |
C20—C21—C16 | 121.8 (2) | H47B—C47—H47C | 109.5 |
C20—C21—H21 | 119.1 | N6—C48—H48A | 109.5 |
C16—C21—H21 | 119.1 | N6—C48—H48B | 109.5 |
N3—C22—H22A | 109.5 | H48A—C48—H48B | 109.5 |
N3—C22—H22B | 109.5 | N6—C48—H48C | 109.5 |
H22A—C22—H22B | 109.5 | H48A—C48—H48C | 109.5 |
N3—C22—H22C | 109.5 | H48B—C48—H48C | 109.5 |
H22A—C22—H22C | 109.5 | C50—C49—C31 | 112.6 (3) |
H22B—C22—H22C | 109.5 | C50—C49—H49A | 109.1 |
N3—C23—H23A | 109.5 | C31—C49—H49A | 109.1 |
N3—C23—H23B | 109.5 | C50—C49—H49B | 109.1 |
H23A—C23—H23B | 109.5 | C31—C49—H49B | 109.1 |
N3—C23—H23C | 109.5 | H49A—C49—H49B | 107.8 |
H23A—C23—H23C | 109.5 | C49—C50—C30 | 111.6 (3) |
H23B—C23—H23C | 109.5 | C49—C50—H50A | 109.3 |
C25—C24—C5 | 113.4 (3) | C30—C50—H50A | 109.3 |
C25—C24—H24A | 108.9 | C49—C50—H50B | 109.3 |
C5—C24—H24A | 108.9 | C30—C50—H50B | 109.3 |
C25—C24—H24B | 108.9 | H50A—C50—H50B | 108.0 |
C4—S1—C1—C2 | 0.1 (2) | C29—S2—C26—C27 | −0.2 (2) |
C4—S1—C1—C5 | 179.2 (2) | C29—S2—C26—C30 | −178.2 (2) |
C5—C1—C2—C3 | −179.2 (2) | C30—C26—C27—C28 | 178.1 (2) |
S1—C1—C2—C3 | −0.2 (3) | S2—C26—C27—C28 | 0.3 (3) |
C5—C1—C2—C6 | −1.7 (4) | C30—C26—C27—C31 | 0.9 (4) |
S1—C1—C2—C6 | 177.36 (19) | S2—C26—C27—C31 | −177.0 (2) |
C1—C2—C3—C4 | 0.2 (3) | C26—C27—C28—C29 | −0.2 (3) |
C6—C2—C3—C4 | −177.1 (2) | C31—C27—C28—C29 | 176.8 (2) |
C1—C2—C3—C7 | 179.8 (2) | C26—C27—C28—C32 | 179.8 (2) |
C6—C2—C3—C7 | 2.4 (4) | C31—C27—C28—C32 | −3.2 (4) |
C2—C3—C4—N2 | −180.0 (2) | C27—C28—C29—N5 | −178.0 (2) |
C7—C3—C4—N2 | 0.5 (4) | C32—C28—C29—N5 | 2.0 (4) |
C2—C3—C4—S1 | −0.2 (3) | C27—C28—C29—S2 | 0.0 (3) |
C7—C3—C4—S1 | −179.69 (19) | C32—C28—C29—S2 | −180.0 (2) |
C15—N2—C4—C3 | −175.3 (2) | C40—N5—C29—C28 | −175.3 (3) |
C15—N2—C4—S1 | 4.9 (3) | C40—N5—C29—S2 | 6.9 (3) |
C1—S1—C4—C3 | 0.07 (19) | C26—S2—C29—C28 | 0.1 (2) |
C1—S1—C4—N2 | 179.9 (2) | C26—S2—C29—N5 | 178.2 (2) |
C2—C1—C5—C24 | 18.2 (4) | C27—C26—C30—C50 | 10.4 (4) |
S1—C1—C5—C24 | −160.8 (2) | S2—C26—C30—C50 | −171.9 (2) |
C1—C2—C6—C25 | 9.5 (4) | C26—C27—C31—C49 | 17.6 (4) |
C3—C2—C6—C25 | −173.3 (3) | C28—C27—C31—C49 | −159.2 (3) |
C8—N1—C7—O1 | −2.1 (4) | C33—N4—C32—O2 | 3.2 (4) |
C8—N1—C7—C3 | 177.5 (2) | C33—N4—C32—C28 | −176.6 (2) |
C4—C3—C7—O1 | 179.5 (3) | C29—C28—C32—O2 | 171.8 (3) |
C2—C3—C7—O1 | 0.0 (4) | C27—C28—C32—O2 | −8.2 (4) |
C4—C3—C7—N1 | −0.1 (4) | C29—C28—C32—N4 | −8.3 (4) |
C2—C3—C7—N1 | −179.6 (2) | C27—C28—C32—N4 | 171.7 (2) |
C7—N1—C8—C9 | −179.0 (3) | C32—N4—C33—C34 | −151.6 (3) |
C7—N1—C8—C13 | 0.9 (4) | C32—N4—C33—C38 | 31.5 (4) |
C13—C8—C9—C10 | −0.8 (4) | C38—C33—C34—C35 | 1.6 (4) |
N1—C8—C9—C10 | 179.1 (3) | N4—C33—C34—C35 | −175.4 (2) |
C8—C9—C10—C11 | 0.0 (5) | C33—C34—C35—C36 | 0.3 (4) |
C9—C10—C11—C12 | 0.8 (5) | C34—C35—C36—C37 | −2.3 (4) |
C9—C10—C11—C14 | −177.1 (3) | C34—C35—C36—C39 | 178.4 (3) |
C10—C11—C12—C13 | −0.9 (5) | C35—C36—C37—C38 | 2.3 (4) |
C14—C11—C12—C13 | 177.0 (3) | C39—C36—C37—C38 | −178.4 (3) |
C9—C8—C13—C12 | 0.7 (4) | C36—C37—C38—C33 | −0.4 (4) |
N1—C8—C13—C12 | −179.2 (3) | C34—C33—C38—C37 | −1.6 (4) |
C11—C12—C13—C8 | 0.1 (5) | N4—C33—C38—C37 | 175.3 (3) |
C4—N2—C15—C16 | 179.9 (2) | C29—N5—C40—C41 | −175.8 (2) |
N2—C15—C16—C17 | 176.3 (3) | N5—C40—C41—C46 | 177.6 (3) |
N2—C15—C16—C21 | −1.3 (4) | N5—C40—C41—C42 | −0.3 (4) |
C21—C16—C17—C18 | −0.5 (4) | C46—C41—C42—C43 | −0.1 (4) |
C15—C16—C17—C18 | −178.2 (3) | C40—C41—C42—C43 | 177.9 (3) |
C16—C17—C18—C19 | 0.0 (4) | C41—C42—C43—C44 | 0.5 (4) |
C22—N3—C19—C18 | −179.5 (3) | C48—N6—C44—C45 | −1.4 (4) |
C23—N3—C19—C18 | 0.3 (4) | C47—N6—C44—C45 | −173.2 (3) |
C22—N3—C19—C20 | 0.9 (4) | C48—N6—C44—C43 | 179.2 (3) |
C23—N3—C19—C20 | −179.3 (3) | C47—N6—C44—C43 | 7.4 (4) |
C17—C18—C19—N3 | −179.1 (3) | C42—C43—C44—N6 | 178.9 (3) |
C17—C18—C19—C20 | 0.6 (4) | C42—C43—C44—C45 | −0.5 (4) |
N3—C19—C20—C21 | 179.0 (3) | N6—C44—C45—C46 | −179.2 (3) |
C18—C19—C20—C21 | −0.7 (4) | C43—C44—C45—C46 | 0.2 (4) |
C19—C20—C21—C16 | 0.1 (4) | C44—C45—C46—C41 | 0.2 (4) |
C17—C16—C21—C20 | 0.4 (4) | C42—C41—C46—C45 | −0.3 (4) |
C15—C16—C21—C20 | 178.1 (3) | C40—C41—C46—C45 | −178.3 (3) |
C1—C5—C24—C25 | −43.8 (4) | C27—C31—C49—C50 | −48.7 (4) |
C5—C24—C25—C6 | 56.0 (5) | C31—C49—C50—C30 | 62.2 (4) |
C2—C6—C25—C24 | −36.8 (4) | C26—C30—C50—C49 | −40.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···N2 | 0.86 (3) | 2.06 (3) | 2.780 (3) | 141 (3) |
N4—H4N···N5 | 0.82 (3) | 2.07 (3) | 2.765 (3) | 141 (3) |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | C23H25N3OS | C25H27N3OS |
Mr | 391.53 | 417.57 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21/n |
Temperature (K) | 293 | 293 |
a, b, c (Å) | 7.8352 (9), 10.7300 (13), 13.1342 (15) | 8.016 (2), 21.255 (6), 25.651 (7) |
α, β, γ (°) | 94.222 (2), 99.965 (2), 108.593 (2) | 90, 98.378 (5), 90 |
V (Å3) | 1020.9 (2) | 4324 (2) |
Z | 2 | 8 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.18 | 0.17 |
Crystal size (mm) | 0.20 × 0.20 × 0.20 | 0.40 × 0.35 × 0.30 |
Data collection | ||
Diffractometer | Bruker SMART CCD area-detector diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1997) | Multi-scan (SADABS; Sheldrick, 1997) |
Tmin, Tmax | 0.908, 0.966 | 0.925, 0.950 |
No. of measured, independent and observed reflections | 10235, 3725, 1678 [I > 2σ(I)] | 33520, 8756, 6163 [I > \2s(I)] |
Rint | 0.086 | 0.034 |
(sin θ/λ)max (Å−1) | 0.602 | 0.625 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.128, 0.94 | 0.059, 0.165, 1.06 |
No. of reflections | 3725 | 8756 |
No. of parameters | 262 | 555 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.19 | 0.49, −0.24 |
Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···N2 | 0.77 (3) | 2.12 (3) | 2.766 (5) | 143 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···N2 | 0.86 (3) | 2.06 (3) | 2.780 (3) | 141 (3) |
N4—H4N···N5 | 0.82 (3) | 2.07 (3) | 2.765 (3) | 141 (3) |
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Most Schiff bases (Pellis & West, 1968; Cohen et al., 1977; Csaszar & Morvay, 1983; Lakshmi et al., 1985) and their thiophene derivatives (El-Meghraby et al., 1982; Dzhurayev et al., 1992; Gewald et al., 1966) possess antibacterial, antitubercular and antifungal activities. Sulfur-containing Schiff bases are particularly effective. The two title compounds, N-(2-methylphenyl)-2-{[(1Z)-(4-dimethylaminophenyl)methylene]amino}- 4,5-dimethylthiophene-3-carboxamide, (I), and N-(2-methylphenyl)-2-{[(1Z)-(4-dimethylaminophenyl)methylene]amino}-4,5,6,7- tetrahydro-1-benzothiophene-3-carboxamide, (II), belong to the same series of compounds and show antibacterial and antifungal activities (Mohan & Saravanan, 2002, 2003).
Compound (I), contains three different structural moieties which will be discussed separately (Fig. 1). The thiophene ring exhibits normal geometry and is planar, with a maximum deviation of 0.0166 (4) Å for atom C4. The o-toluidine group is in a gauche conformation with respect to the plane of the thiophene ring, as indicated by the C7—N1—C8—C9 torsion angle of −137.4 (4)°. The angle between the mean planes of the o-toluidide and thiophene rings is 56.44 (11)°.
The dimethylamino group is coplanar with its attached phenyl ring [C20—C19—N3—C22 = −1.1 (5)°]. The p-(dimethylamino)phenyl moiety is also coplanar with the thiophene ring; the angle between the planes of these two rings is 3.25 (15)°. It is interesting to note that the angles C18—C19—C20 [116.4 (4)°] and C17—C16—C21 [115.9 (4)°] deviate significantly from the ideal value of 120° for a phenyl ring. This deviation is due to the electron-donating effect of the –N(CH3)2 group attached to C19.
Compound (II) crystallizes with two crystallographically independent molecules (A and B) in the asymmetric unit (Fig. 2). This compound also contains three different structural moieties. The thiophene ring exhibits normal geometry in both symmetry-independent molecules. The p-toluidine group is coplanar with the thiophene ring in molecule A [C7—N1—C8—C9 = −179.0 (3)°], while it is tilted from the thiophene ring in molecule B [C32—N4—C33—C34 = −151.6 (3)°]. The angles between the mean planes of the p-toluidine and thiophene rings in molecules A and B are 2.96 (8) and 25.18 (8)°, respectively.
The dimethylamino group is coplanar with its attached phenyl ring in molecule A [C20—C19—N3—C22 = 0.9 (4)°], whereas in molecule B, it is slightly tilted [C43—C44—N6—C47 = 7.4 (4)°]. The dimethylamino moiety is essentially coplanar with the thiophene ring; the angles between the mean planes of these moieties in molecules A and B are 2.48 (8) and 9.38 (8)°, respectively. The angles C18—C19—C20 [117.0 (2)°] and C17—C16—C21 [116.7 (2)°] in molecule A, and C43—C44—C45 [116.6 (2)°] and C42—C41—C46 [117.0 (2)°] in molecule B again deviate significantly from the ideal value of 120° for a phenyl ring, as was observed in the case of compound (I).
There are no significant intermolecular hydrogen-bonding interactions in the packing of compounds (I) and (II). The packing is essentially stabilized via weak van der Waals forces. However, there is a significant intramolecular N—H···N hydrogen-bonding interaction in each structure, which locks the molecule into a rigid pseudo-six-membered ring conformation and removes the conformational flexibility (Figs 1 and 2, and Tables 1 and 2). Hence, the free N—H group is not available to participate in intermolecular interactions.