Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The two title compounds, 2-({(1Z)-[4-(di­methyl­amino)phenyl]methylene}amino)-4,5-dimethyl-N-(2-methylphenyl)thiophene-3-carboxamide, C23H25N3OS, (I), and 2-({(1E)-[4-(dimethylamino)phenyl]methylene}amino)-N-(4-methylphenyl)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide,C25H27N3OS, (II), show antibacterial and antifungal activities. The asymmetric unit of (II) contains two crystallographically independent mol­ecules. The o-toluidine ring in (I) lies gauche with respect to the thio­phene ring. In (II), the p-toluidine ring is coplanar with the thio­phene ring in one mol­ecule, but is tilted from it in the other mol­ecule. Neither structure exhibits any significant intermolecular interactions, but in both, an intramolecular N—H...N hydrogen bond forms a pseudo-six-membered ring, thus locking the molecular conformation and removing conformational flexibility.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103023205/ln1181sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103023205/ln1181Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103023205/ln1181IIsup3.hkl
Contains datablock II

CCDC references: 229097; 229098

Comment top

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.

Experimental top

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).

Refinement top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. View of the molecule of compound (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented by circles of arbitrary size.
[Figure 2] Fig. 2. View of the asymmetric unit of compound (II), showing the two symmetry-independent molecules and the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented by circles of arbitrary size.
(I) 2-{[(1Z)-(4-dimethylaminophenyl)methylene]amino}-4,5-dimethyl- N-(2-methylphenyl)thiophene-3-carboxamide top
Crystal data top
C23H25N3OSZ = 2
Mr = 391.53F(000) = 416
Triclinic, P1Dx = 1.274 Mg m3
Hall symbol: -P 1Melting point: 419 K
a = 7.8352 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.7300 (13) ÅCell parameters from 835 reflections
c = 13.1342 (15) Åθ = 2.3–21.2°
α = 94.222 (2)°µ = 0.18 mm1
β = 99.965 (2)°T = 293 K
γ = 108.593 (2)°Prism, red
V = 1020.9 (2) Å30.20 × 0.20 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3725 independent reflections
Radiation source: sealed tube1678 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.086
ϕ and ω scansθmax = 25.4°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
h = 99
Tmin = 0.908, Tmax = 0.966k = 1212
10235 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H 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 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C23H25N3OSγ = 108.593 (2)°
Mr = 391.53V = 1020.9 (2) Å3
Triclinic, P1Z = 2
a = 7.8352 (9) ÅMo Kα radiation
b = 10.7300 (13) ŵ = 0.18 mm1
c = 13.1342 (15) ÅT = 293 K
α = 94.222 (2)°0.20 × 0.20 × 0.20 mm
β = 99.965 (2)°
Data collection top
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 = 0.966Rint = 0.086
10235 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0660 restraints
wR(F2) = 0.128H atoms treated by a mixture of independent and constrained refinement
S = 0.94Δρmax = 0.20 e Å3
3725 reflectionsΔρmin = 0.19 e Å3
262 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.45958 (14)0.11614 (10)0.91004 (8)0.0566 (4)
N10.4066 (5)0.4322 (4)0.6994 (3)0.0537 (10)
N20.5671 (4)0.3821 (3)0.8896 (2)0.0465 (8)
N31.1599 (4)0.8933 (3)1.2015 (3)0.0582 (9)
O10.1575 (4)0.2684 (2)0.6062 (2)0.0605 (8)
C10.3046 (5)0.0072 (4)0.8072 (3)0.0487 (10)
C20.2489 (5)0.0714 (4)0.7284 (3)0.0461 (10)
C30.3344 (5)0.2130 (4)0.7515 (3)0.0409 (9)
C40.4570 (5)0.2535 (4)0.8472 (3)0.0434 (10)
C50.2512 (5)0.1394 (4)0.8118 (3)0.0728 (13)
H5A0.15180.18630.75430.109*
H5B0.21280.15820.87630.109*
H5C0.35500.16740.80800.109*
C60.1223 (5)0.0025 (4)0.6274 (3)0.0637 (12)
H6A0.09320.09630.62860.096*
H6B0.18180.02270.57040.096*
H6C0.01110.01890.61880.096*
C70.2899 (5)0.3061 (4)0.6797 (3)0.0440 (10)
C80.4023 (5)0.5383 (4)0.6427 (3)0.0446 (10)
C90.5653 (5)0.6229 (4)0.6236 (3)0.0468 (10)
C100.5614 (6)0.7287 (4)0.5700 (3)0.0652 (13)
H100.67030.78620.55730.078*
C110.3969 (7)0.7498 (4)0.5350 (3)0.0716 (14)
H110.39590.82160.49960.086*
C120.2354 (6)0.6647 (4)0.5526 (3)0.0657 (13)
H120.12480.67810.52800.079*
C130.2363 (6)0.5593 (4)0.6068 (3)0.0574 (11)
H130.12680.50250.61940.069*
C140.7452 (5)0.5998 (4)0.6579 (3)0.0699 (13)
H14A0.78460.62190.73230.105*
H14B0.83650.65470.62500.105*
H14C0.72910.50820.63830.105*
C150.6727 (5)0.4037 (4)0.9796 (3)0.0484 (11)
H150.66790.33041.01410.058*
C160.7976 (5)0.5299 (4)1.0323 (3)0.0441 (10)
C170.9062 (5)0.5376 (4)1.1308 (3)0.0524 (11)
H170.89540.46001.16030.063*
C181.0276 (5)0.6550 (4)1.1852 (3)0.0507 (11)
H181.09930.65481.24950.061*
C191.0459 (5)0.7756 (4)1.1459 (3)0.0459 (10)
C200.9382 (5)0.7680 (4)1.0463 (3)0.0530 (11)
H200.94880.84521.01610.064*
C210.8186 (5)0.6495 (4)0.9933 (3)0.0529 (11)
H210.74820.64880.92840.063*
C221.1799 (6)1.0188 (4)1.1603 (3)0.0745 (14)
H22A1.22471.01701.09690.112*
H22B1.26561.09051.21060.112*
H22C1.06261.03141.14640.112*
C231.2700 (5)0.8971 (4)1.3033 (3)0.0676 (13)
H23A1.19050.86001.34940.101*
H23B1.34270.98751.33110.101*
H23C1.34970.84651.29670.101*
H1N0.482 (4)0.451 (3)0.749 (2)0.037 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0650 (8)0.0543 (8)0.0487 (7)0.0224 (6)0.0011 (6)0.0152 (6)
N10.052 (3)0.052 (3)0.048 (3)0.013 (2)0.008 (2)0.015 (2)
N20.044 (2)0.054 (2)0.039 (2)0.0186 (18)0.0018 (17)0.0053 (17)
N30.062 (2)0.052 (2)0.051 (2)0.0140 (19)0.0030 (19)0.0043 (19)
O10.0601 (18)0.0600 (19)0.0527 (18)0.0185 (15)0.0092 (15)0.0128 (15)
C10.052 (3)0.045 (3)0.048 (2)0.019 (2)0.004 (2)0.009 (2)
C20.044 (2)0.046 (3)0.047 (3)0.016 (2)0.004 (2)0.004 (2)
C30.037 (2)0.050 (3)0.038 (2)0.017 (2)0.0082 (19)0.013 (2)
C40.046 (2)0.049 (3)0.039 (2)0.018 (2)0.010 (2)0.011 (2)
C50.078 (3)0.055 (3)0.079 (3)0.021 (3)0.001 (3)0.018 (3)
C60.065 (3)0.053 (3)0.061 (3)0.016 (2)0.008 (2)0.003 (2)
C70.041 (3)0.051 (3)0.038 (2)0.015 (2)0.005 (2)0.004 (2)
C80.052 (3)0.046 (3)0.036 (2)0.018 (2)0.004 (2)0.009 (2)
C90.052 (3)0.040 (2)0.043 (2)0.010 (2)0.007 (2)0.002 (2)
C100.076 (4)0.053 (3)0.054 (3)0.004 (3)0.013 (2)0.013 (2)
C110.096 (4)0.057 (3)0.059 (3)0.028 (3)0.000 (3)0.022 (2)
C120.068 (3)0.064 (3)0.062 (3)0.030 (3)0.010 (2)0.006 (3)
C130.061 (3)0.057 (3)0.053 (3)0.021 (2)0.006 (2)0.009 (2)
C140.050 (3)0.080 (3)0.080 (3)0.019 (2)0.015 (2)0.019 (3)
C150.052 (3)0.052 (3)0.045 (3)0.020 (2)0.009 (2)0.017 (2)
C160.046 (3)0.054 (3)0.039 (2)0.025 (2)0.007 (2)0.012 (2)
C170.058 (3)0.052 (3)0.047 (3)0.021 (2)0.002 (2)0.016 (2)
C180.050 (3)0.059 (3)0.044 (3)0.024 (2)0.001 (2)0.012 (2)
C190.046 (3)0.052 (3)0.043 (3)0.020 (2)0.009 (2)0.007 (2)
C200.067 (3)0.049 (3)0.046 (3)0.023 (2)0.008 (2)0.017 (2)
C210.061 (3)0.064 (3)0.036 (2)0.027 (3)0.002 (2)0.012 (2)
C220.088 (4)0.060 (3)0.073 (3)0.021 (3)0.016 (3)0.015 (3)
C230.064 (3)0.071 (3)0.058 (3)0.021 (2)0.002 (2)0.004 (2)
Geometric parameters (Å, º) top
S1—C11.721 (4)C10—H100.9300
S1—C41.745 (4)C11—C121.373 (5)
N1—C71.346 (5)C11—H110.9300
N1—C81.411 (5)C12—C131.381 (5)
N1—H1N0.76 (3)C12—H120.9300
N2—C151.278 (4)C13—H130.9300
N2—C41.386 (4)C14—H14A0.9600
N3—C191.359 (4)C14—H14B0.9600
N3—C231.449 (4)C14—H14C0.9600
N3—C221.461 (4)C15—C161.434 (5)
O1—C71.225 (4)C15—H150.9300
C1—C21.370 (4)C16—C211.388 (5)
C1—C51.502 (5)C16—C171.401 (4)
C2—C31.435 (5)C17—C181.367 (5)
C2—C61.503 (5)C17—H170.9300
C3—C41.389 (4)C18—C191.402 (5)
C3—C71.502 (5)C18—H180.9300
C5—H5A0.9600C19—C201.411 (5)
C5—H5B0.9600C20—C211.365 (5)
C5—H5C0.9600C20—H200.9300
C6—H6A0.9600C21—H210.9300
C6—H6B0.9600C22—H22A0.9600
C6—H6C0.9600C22—H22B0.9600
C8—C91.387 (5)C22—H22C0.9600
C8—C131.398 (5)C23—H23A0.9600
C9—C101.385 (5)C23—H23B0.9600
C9—C141.507 (5)C23—H23C0.9600
C10—C111.386 (5)
C1—S1—C492.35 (19)C10—C11—H11120.0
C7—N1—C8128.1 (4)C11—C12—C13120.3 (4)
C7—N1—H1N118 (3)C11—C12—H12119.8
C8—N1—H1N114 (3)C13—C12—H12119.8
C15—N2—C4119.7 (3)C12—C13—C8119.8 (4)
C19—N3—C23120.4 (3)C12—C13—H13120.1
C19—N3—C22121.6 (3)C8—C13—H13120.1
C23—N3—C22117.9 (3)C9—C14—H14A109.5
C2—C1—C5128.7 (3)C9—C14—H14B109.5
C2—C1—S1112.1 (3)H14A—C14—H14B109.5
C5—C1—S1119.2 (3)C9—C14—H14C109.5
C1—C2—C3112.3 (3)H14A—C14—H14C109.5
C1—C2—C6122.1 (3)H14B—C14—H14C109.5
C3—C2—C6125.4 (3)N2—C15—C16126.3 (3)
C4—C3—C2113.1 (3)N2—C15—H15116.9
C4—C3—C7124.2 (3)C16—C15—H15116.9
C2—C3—C7122.7 (3)C21—C16—C17115.9 (4)
N2—C4—C3127.1 (3)C21—C16—C15124.4 (3)
N2—C4—S1122.8 (3)C17—C16—C15119.6 (4)
C3—C4—S1110.1 (3)C18—C17—C16122.5 (4)
C1—C5—H5A109.5C18—C17—H17118.8
C1—C5—H5B109.5C16—C17—H17118.8
H5A—C5—H5B109.5C17—C18—C19121.2 (4)
C1—C5—H5C109.5C17—C18—H18119.4
H5A—C5—H5C109.5C19—C18—H18119.4
H5B—C5—H5C109.5N3—C19—C18121.6 (4)
C2—C6—H6A109.5N3—C19—C20122.0 (4)
C2—C6—H6B109.5C18—C19—C20116.4 (4)
H6A—C6—H6B109.5C21—C20—C19121.2 (4)
C2—C6—H6C109.5C21—C20—H20119.4
H6A—C6—H6C109.5C19—C20—H20119.4
H6B—C6—H6C109.5C20—C21—C16122.7 (4)
O1—C7—N1122.1 (4)C20—C21—H21118.6
O1—C7—C3121.8 (4)C16—C21—H21118.6
N1—C7—C3116.1 (3)N3—C22—H22A109.5
C9—C8—C13120.0 (4)N3—C22—H22B109.5
C9—C8—N1119.3 (4)H22A—C22—H22B109.5
C13—C8—N1120.7 (4)N3—C22—H22C109.5
C10—C9—C8119.2 (4)H22A—C22—H22C109.5
C10—C9—C14119.6 (4)H22B—C22—H22C109.5
C8—C9—C14121.2 (3)N3—C23—H23A109.5
C9—C10—C11120.7 (4)N3—C23—H23B109.5
C9—C10—H10119.6H23A—C23—H23B109.5
C11—C10—H10119.6N3—C23—H23C109.5
C12—C11—C10120.0 (4)H23A—C23—H23C109.5
C12—C11—H11120.0H23B—C23—H23C109.5
C4—S1—C1—C21.2 (3)N1—C8—C9—C10178.6 (4)
C4—S1—C1—C5177.5 (3)C13—C8—C9—C14177.8 (4)
C5—C1—C2—C3178.3 (4)N1—C8—C9—C142.8 (5)
S1—C1—C2—C30.3 (4)C8—C9—C10—C110.4 (6)
C5—C1—C2—C62.2 (6)C14—C9—C10—C11178.2 (4)
S1—C1—C2—C6176.3 (3)C9—C10—C11—C120.6 (6)
C1—C2—C3—C41.2 (4)C10—C11—C12—C131.2 (6)
C6—C2—C3—C4174.8 (3)C11—C12—C13—C80.8 (6)
C1—C2—C3—C7177.2 (3)C9—C8—C13—C120.2 (6)
C6—C2—C3—C76.9 (6)N1—C8—C13—C12179.2 (4)
C15—N2—C4—C3179.5 (3)C4—N2—C15—C16178.2 (3)
C15—N2—C4—S11.8 (5)N2—C15—C16—C211.7 (6)
C2—C3—C4—N2176.8 (3)N2—C15—C16—C17179.4 (4)
C7—C3—C4—N24.9 (6)C21—C16—C17—C180.8 (6)
C2—C3—C4—S12.0 (4)C15—C16—C17—C18179.8 (4)
C7—C3—C4—S1176.3 (3)C16—C17—C18—C191.8 (6)
C1—S1—C4—N2177.0 (3)C23—N3—C19—C181.3 (5)
C1—S1—C4—C31.8 (3)C22—N3—C19—C18179.6 (3)
C8—N1—C7—O11.0 (6)C23—N3—C19—C20179.4 (3)
C8—N1—C7—C3177.3 (4)C22—N3—C19—C201.1 (5)
C4—C3—C7—O1166.1 (4)C17—C18—C19—N3177.0 (4)
C2—C3—C7—O112.1 (5)C17—C18—C19—C202.4 (5)
C4—C3—C7—N115.6 (5)N3—C19—C20—C21177.3 (4)
C2—C3—C7—N1166.3 (3)C18—C19—C20—C212.1 (5)
C7—N1—C8—C9137.4 (4)C19—C20—C21—C161.2 (6)
C7—N1—C8—C1343.2 (6)C17—C16—C21—C200.5 (6)
C13—C8—C9—C100.8 (5)C15—C16—C21—C20179.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···N20.77 (3)2.12 (3)2.766 (5)143 (3)
(II) 2-({(1E)-[4-(dimethylamino)phenyl]methylene}amino)- N-(4-methylphenyl)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide top
Crystal data top
C25H27N3OSF(000) = 1776
Mr = 417.57Dx = 1.283 Mg m3
Monoclinic, P21/nMelting point: 497 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 8.016 (2) ÅCell parameters from 839 reflections
b = 21.255 (6) Åθ = 2.6–21.4°
c = 25.651 (7) ŵ = 0.17 mm1
β = 98.378 (5)°T = 293 K
V = 4324 (2) Å3Prism, yellow
Z = 80.40 × 0.35 × 0.30 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
8756 independent reflections
Radiation source: fine-focus sealed tube6163 reflections with I > \2s(I)
Graphite monochromatorRint = 0.034
ϕ and ω scansθmax = 26.4°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
h = 1010
Tmin = 0.925, Tmax = 0.950k = 2426
33520 measured reflectionsl = 3131
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165H 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 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C25H27N3OSV = 4324 (2) Å3
Mr = 417.57Z = 8
Monoclinic, P21/nMo Kα radiation
a = 8.016 (2) ŵ = 0.17 mm1
b = 21.255 (6) ÅT = 293 K
c = 25.651 (7) Å0.40 × 0.35 × 0.30 mm
β = 98.378 (5)°
Data collection top
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 = 0.950Rint = 0.034
33520 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.165H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.49 e Å3
8756 reflectionsΔρmin = 0.24 e Å3
555 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
xyzUiso*/Ueq
S10.49293 (9)0.01762 (3)0.19855 (3)0.05455 (19)
S20.73415 (10)0.48537 (3)0.03428 (3)0.0618 (2)
O10.5845 (3)0.20764 (9)0.16755 (8)0.0805 (7)
O20.6664 (3)0.71180 (9)0.06871 (8)0.0754 (6)
N10.6575 (3)0.14875 (11)0.10127 (9)0.0543 (6)
N20.6188 (3)0.01925 (10)0.10899 (8)0.0497 (5)
N30.8363 (3)0.13307 (10)0.08932 (9)0.0612 (6)
N40.6033 (3)0.65224 (11)0.13611 (9)0.0569 (6)
N50.6625 (3)0.52438 (10)0.13115 (9)0.0530 (5)
N60.5321 (3)0.37217 (10)0.34057 (9)0.0642 (6)
C10.4512 (3)0.04110 (12)0.24113 (10)0.0496 (6)
C20.4868 (3)0.09932 (11)0.22411 (10)0.0474 (6)
C30.5520 (3)0.09745 (11)0.17417 (9)0.0461 (6)
C40.5618 (3)0.03659 (12)0.15547 (10)0.0471 (6)
C50.3801 (4)0.02584 (13)0.29086 (11)0.0602 (7)
H5A0.46920.01070.31760.072*
H5B0.29570.00700.28390.072*
C60.4516 (4)0.15717 (12)0.25497 (11)0.0574 (7)
H6A0.36070.18080.23490.069*
H6B0.55110.18370.25980.069*
C70.5993 (3)0.15607 (12)0.14775 (10)0.0491 (6)
C80.7053 (3)0.19525 (11)0.06719 (10)0.0478 (6)
C90.7590 (4)0.17645 (13)0.02096 (11)0.0641 (8)
H90.76420.13370.01350.077*
C100.8053 (4)0.21969 (13)0.01445 (11)0.0665 (8)
H100.84080.20530.04530.080*
C110.8003 (3)0.28335 (13)0.00546 (11)0.0552 (6)
C120.7488 (4)0.30153 (13)0.04093 (12)0.0691 (8)
H120.74550.34430.04850.083*
C130.7015 (4)0.25907 (13)0.07709 (12)0.0661 (8)
H130.66730.27360.10800.079*
C140.8436 (4)0.33057 (15)0.04576 (12)0.0751 (9)
H14A0.74400.34040.06990.113*
H14B0.92710.31290.06480.113*
H14C0.88710.36820.02810.113*
C150.6116 (3)0.03865 (12)0.09393 (11)0.0548 (6)
H150.56750.06780.11530.066*
C160.6668 (3)0.06147 (12)0.04646 (10)0.0504 (6)
C170.6627 (4)0.12578 (12)0.03521 (11)0.0578 (7)
H170.62080.15320.05840.069*
C180.7183 (3)0.15002 (12)0.00884 (11)0.0574 (7)
H180.71330.19320.01490.069*
C190.7827 (3)0.11019 (12)0.04496 (10)0.0504 (6)
C200.7884 (4)0.04532 (12)0.03343 (10)0.0571 (7)
H200.83130.01770.05630.069*
C210.7323 (4)0.02214 (12)0.01065 (11)0.0570 (7)
H210.73770.02090.01700.068*
C220.9040 (4)0.09195 (14)0.12622 (11)0.0679 (8)
H22A0.82030.06140.13970.102*
H22B0.93440.11640.15480.102*
H22C1.00200.07080.10860.102*
C230.8283 (4)0.19981 (13)0.10115 (12)0.0713 (8)
H23A0.90640.22200.07570.107*
H23B0.85700.20670.13580.107*
H23C0.71610.21490.09980.107*
C240.3008 (5)0.08503 (16)0.31048 (15)0.0916 (11)
H24A0.19180.09190.28930.110*
H24B0.28220.07840.34660.110*
C250.4036 (5)0.14124 (17)0.30827 (14)0.0885 (11)
H25A0.50640.13610.33300.106*
H25B0.34300.17680.32010.106*
C260.7441 (3)0.54270 (12)0.01281 (10)0.0527 (6)
C270.7157 (3)0.60131 (11)0.00552 (10)0.0486 (6)
C280.6853 (3)0.60080 (11)0.05956 (10)0.0483 (6)
C290.6913 (3)0.54086 (12)0.08058 (10)0.0493 (6)
C300.7750 (4)0.52575 (13)0.06734 (11)0.0637 (7)
H30A0.67890.50280.08530.076*
H30B0.87340.49880.06530.076*
C310.7106 (4)0.65737 (12)0.03070 (10)0.0581 (7)
H31A0.81530.68070.02300.070*
H31B0.61910.68500.02460.070*
C320.6515 (3)0.66003 (12)0.08804 (10)0.0516 (6)
C330.5562 (3)0.69912 (11)0.16980 (10)0.0498 (6)
C340.5828 (3)0.68879 (13)0.22380 (11)0.0574 (7)
H340.63850.65250.23710.069*
C350.5278 (4)0.73148 (14)0.25817 (12)0.0633 (7)
H350.54790.72350.29420.076*
C360.4435 (4)0.78603 (14)0.24023 (13)0.0647 (8)
C370.4225 (4)0.79665 (13)0.18636 (13)0.0665 (8)
H370.37000.83360.17330.080*
C380.4762 (3)0.75476 (13)0.15124 (11)0.0590 (7)
H380.45920.76360.11530.071*
C390.3793 (5)0.83195 (17)0.27746 (15)0.0955 (12)
H39A0.31890.86520.25760.143*
H39B0.47280.84930.30060.143*
H39C0.30530.81060.29780.143*
C400.6831 (3)0.46715 (12)0.14748 (11)0.0545 (6)
H400.72470.43830.12530.065*
C410.6464 (3)0.44458 (12)0.19742 (10)0.0526 (6)
C420.5840 (3)0.48311 (12)0.23438 (11)0.0563 (7)
H420.56840.52580.22710.068*
C430.5455 (3)0.45996 (12)0.28058 (11)0.0576 (7)
H430.50350.48700.30400.069*
C440.5680 (3)0.39541 (12)0.29384 (11)0.0528 (6)
C450.6305 (4)0.35677 (12)0.25661 (11)0.0609 (7)
H450.64690.31410.26360.073*
C460.6678 (4)0.38104 (12)0.21003 (11)0.0600 (7)
H460.70860.35420.18620.072*
C470.4505 (4)0.41090 (14)0.37606 (12)0.0683 (8)
H47A0.52070.44650.38710.102*
H47B0.43310.38660.40630.102*
H47C0.34380.42530.35820.102*
C480.5539 (4)0.30584 (14)0.35324 (13)0.0790 (9)
H48A0.46970.28190.33130.119*
H48B0.54240.29930.38960.119*
H48C0.66390.29250.34720.119*
C490.6853 (5)0.63665 (15)0.08820 (12)0.0804 (10)
H49A0.57010.62240.09790.096*
H49B0.70250.67250.11020.096*
C500.8031 (5)0.58504 (15)0.09847 (13)0.0845 (10)
H50A0.91850.59920.08880.101*
H50B0.78630.57530.13580.101*
H4N0.604 (4)0.6164 (15)0.1484 (12)0.072 (10)*
H1N0.663 (4)0.1110 (15)0.0894 (11)0.069 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0662 (4)0.0421 (4)0.0574 (4)0.0004 (3)0.0161 (3)0.0057 (3)
S20.0821 (5)0.0381 (4)0.0686 (5)0.0041 (3)0.0221 (4)0.0001 (3)
O10.138 (2)0.0450 (12)0.0677 (13)0.0149 (12)0.0447 (13)0.0060 (10)
O20.1304 (19)0.0373 (11)0.0638 (12)0.0113 (11)0.0324 (12)0.0025 (9)
N10.0729 (15)0.0364 (12)0.0580 (14)0.0003 (10)0.0240 (11)0.0018 (10)
N20.0579 (12)0.0419 (12)0.0500 (12)0.0028 (9)0.0099 (10)0.0002 (9)
N30.0882 (17)0.0421 (13)0.0555 (13)0.0041 (11)0.0177 (12)0.0008 (10)
N40.0764 (16)0.0394 (13)0.0575 (14)0.0018 (11)0.0188 (11)0.0022 (11)
N50.0591 (13)0.0421 (12)0.0584 (13)0.0013 (9)0.0109 (10)0.0041 (10)
N60.0878 (17)0.0424 (13)0.0656 (15)0.0108 (11)0.0217 (13)0.0085 (11)
C10.0494 (13)0.0500 (15)0.0502 (14)0.0009 (11)0.0102 (11)0.0041 (12)
C20.0459 (13)0.0449 (14)0.0513 (14)0.0011 (10)0.0075 (11)0.0020 (11)
C30.0473 (13)0.0433 (14)0.0481 (14)0.0002 (10)0.0081 (11)0.0014 (11)
C40.0473 (13)0.0440 (14)0.0503 (14)0.0012 (10)0.0085 (11)0.0055 (11)
C50.0653 (17)0.0604 (18)0.0573 (16)0.0009 (13)0.0171 (13)0.0096 (13)
C60.0664 (17)0.0485 (16)0.0606 (16)0.0039 (12)0.0197 (13)0.0052 (13)
C70.0561 (15)0.0429 (14)0.0492 (14)0.0023 (11)0.0106 (11)0.0006 (11)
C80.0529 (14)0.0406 (14)0.0514 (14)0.0007 (10)0.0126 (11)0.0061 (11)
C90.098 (2)0.0403 (15)0.0575 (17)0.0006 (14)0.0241 (15)0.0009 (13)
C100.097 (2)0.0537 (18)0.0539 (16)0.0025 (15)0.0277 (15)0.0015 (13)
C110.0593 (16)0.0530 (16)0.0532 (15)0.0052 (12)0.0072 (12)0.0076 (12)
C120.098 (2)0.0375 (15)0.078 (2)0.0002 (14)0.0353 (17)0.0036 (14)
C130.091 (2)0.0448 (16)0.0703 (19)0.0036 (14)0.0384 (16)0.0010 (14)
C140.096 (2)0.064 (2)0.0659 (19)0.0155 (17)0.0165 (17)0.0155 (15)
C150.0610 (16)0.0449 (15)0.0602 (16)0.0009 (12)0.0143 (13)0.0046 (12)
C160.0567 (15)0.0393 (13)0.0555 (15)0.0015 (11)0.0091 (12)0.0003 (11)
C170.0710 (17)0.0422 (15)0.0628 (17)0.0042 (12)0.0188 (14)0.0023 (12)
C180.0735 (18)0.0347 (13)0.0646 (17)0.0029 (12)0.0125 (14)0.0048 (12)
C190.0578 (15)0.0395 (13)0.0524 (15)0.0040 (11)0.0036 (12)0.0007 (11)
C200.0801 (19)0.0379 (14)0.0553 (16)0.0016 (12)0.0163 (14)0.0046 (12)
C210.0804 (19)0.0321 (13)0.0594 (16)0.0002 (12)0.0128 (14)0.0016 (12)
C220.085 (2)0.0618 (19)0.0601 (18)0.0041 (15)0.0207 (15)0.0013 (14)
C230.095 (2)0.0481 (17)0.0716 (19)0.0058 (15)0.0158 (17)0.0126 (14)
C240.125 (3)0.072 (2)0.090 (3)0.008 (2)0.058 (2)0.0021 (19)
C250.124 (3)0.071 (2)0.082 (2)0.011 (2)0.056 (2)0.0100 (18)
C260.0567 (15)0.0451 (15)0.0577 (16)0.0019 (11)0.0131 (12)0.0023 (12)
C270.0508 (14)0.0425 (14)0.0523 (15)0.0074 (11)0.0065 (11)0.0033 (11)
C280.0512 (14)0.0395 (14)0.0540 (15)0.0056 (10)0.0071 (11)0.0025 (11)
C290.0528 (14)0.0400 (13)0.0558 (15)0.0030 (11)0.0097 (11)0.0021 (11)
C300.0791 (19)0.0526 (17)0.0625 (17)0.0007 (14)0.0203 (15)0.0076 (13)
C310.0786 (19)0.0442 (15)0.0517 (15)0.0060 (13)0.0103 (13)0.0013 (12)
C320.0596 (16)0.0404 (15)0.0544 (15)0.0053 (11)0.0075 (12)0.0039 (11)
C330.0554 (14)0.0376 (13)0.0579 (16)0.0052 (11)0.0135 (12)0.0023 (11)
C340.0639 (16)0.0454 (15)0.0648 (18)0.0011 (12)0.0160 (13)0.0041 (13)
C350.0748 (19)0.0600 (18)0.0584 (17)0.0082 (14)0.0205 (14)0.0056 (14)
C360.0690 (18)0.0504 (17)0.079 (2)0.0077 (14)0.0270 (15)0.0143 (15)
C370.0699 (18)0.0448 (16)0.086 (2)0.0067 (13)0.0144 (15)0.0019 (15)
C380.0683 (17)0.0473 (15)0.0611 (17)0.0011 (13)0.0088 (13)0.0005 (13)
C390.114 (3)0.073 (2)0.108 (3)0.005 (2)0.048 (2)0.024 (2)
C400.0596 (15)0.0444 (15)0.0591 (16)0.0002 (12)0.0068 (12)0.0015 (12)
C410.0563 (15)0.0427 (14)0.0574 (16)0.0012 (11)0.0036 (12)0.0033 (12)
C420.0660 (16)0.0356 (14)0.0682 (17)0.0069 (12)0.0123 (13)0.0090 (12)
C430.0682 (17)0.0412 (14)0.0651 (17)0.0087 (12)0.0158 (14)0.0001 (13)
C440.0559 (15)0.0429 (14)0.0590 (16)0.0031 (11)0.0061 (12)0.0053 (12)
C450.0800 (19)0.0361 (14)0.0664 (18)0.0081 (13)0.0100 (14)0.0062 (13)
C460.0804 (19)0.0403 (14)0.0597 (17)0.0068 (13)0.0110 (14)0.0009 (12)
C470.077 (2)0.0629 (19)0.0667 (19)0.0073 (15)0.0178 (15)0.0030 (15)
C480.101 (2)0.0553 (19)0.086 (2)0.0148 (17)0.0297 (19)0.0219 (16)
C490.129 (3)0.0529 (18)0.0586 (18)0.0031 (18)0.0129 (18)0.0000 (14)
C500.129 (3)0.065 (2)0.067 (2)0.002 (2)0.039 (2)0.0001 (16)
Geometric parameters (Å, º) top
S1—C11.723 (3)C22—H22A0.9600
S1—C41.741 (3)C22—H22B0.9600
S2—C261.726 (3)C22—H22C0.9600
S2—C291.743 (3)C23—H23A0.9600
O1—C71.221 (3)C23—H23B0.9600
O2—C321.220 (3)C23—H23C0.9600
N1—C71.351 (3)C24—C251.457 (5)
N1—C81.409 (3)C24—H24A0.9700
N1—H1N0.86 (3)C24—H24B0.9700
N2—C151.289 (3)C25—H25A0.9700
N2—C41.387 (3)C25—H25B0.9700
N3—C191.363 (3)C26—C271.363 (3)
N3—C221.450 (3)C26—C301.499 (4)
N3—C231.450 (4)C27—C281.442 (4)
N4—C321.355 (3)C27—C311.508 (3)
N4—C331.406 (3)C28—C291.381 (3)
N4—H4N0.82 (3)C28—C321.500 (3)
N5—C401.289 (3)C30—C501.526 (4)
N5—C291.395 (3)C30—H30A0.9700
N6—C441.365 (3)C30—H30B0.9700
N6—C481.452 (4)C31—C491.524 (4)
N6—C471.452 (4)C31—H31A0.9700
C1—C21.356 (3)C31—H31B0.9700
C1—C51.506 (4)C33—C341.388 (4)
C2—C31.453 (3)C33—C381.396 (4)
C2—C61.511 (3)C34—C351.381 (4)
C3—C41.386 (3)C34—H340.9300
C3—C71.494 (3)C35—C361.387 (4)
C5—C241.527 (4)C35—H350.9300
C5—H5A0.9700C36—C371.386 (4)
C5—H5B0.9700C36—C391.508 (4)
C6—C251.511 (4)C37—C381.379 (4)
C6—H6A0.9700C37—H370.9300
C6—H6B0.9700C38—H380.9300
C8—C91.379 (4)C39—H39A0.9600
C8—C131.381 (4)C39—H39B0.9600
C9—C101.380 (4)C39—H39C0.9600
C9—H90.9300C40—C411.438 (4)
C10—C111.374 (4)C40—H400.9300
C10—H100.9300C41—C461.393 (4)
C11—C121.371 (4)C41—C421.399 (4)
C11—C141.517 (4)C42—C431.360 (4)
C12—C131.386 (4)C42—H420.9300
C12—H120.9300C43—C441.419 (4)
C13—H130.9300C43—H430.9300
C14—H14A0.9600C44—C451.406 (4)
C14—H14B0.9600C45—C461.374 (4)
C14—H14C0.9600C45—H450.9300
C15—C161.439 (4)C46—H460.9300
C15—H150.9300C47—H47A0.9600
C16—C171.397 (4)C47—H47B0.9600
C16—C211.399 (4)C47—H47C0.9600
C17—C181.374 (4)C48—H48A0.9600
C17—H170.9300C48—H48B0.9600
C18—C191.407 (4)C48—H48C0.9600
C18—H180.9300C49—C501.495 (5)
C19—C201.410 (4)C49—H49A0.9700
C20—C211.369 (4)C49—H49B0.9700
C20—H200.9300C50—H50A0.9700
C21—H210.9300C50—H50B0.9700
C1—S1—C491.82 (12)C5—C24—H24B108.9
C26—S2—C2991.89 (13)H24A—C24—H24B107.7
C7—N1—C8128.8 (2)C24—C25—C6116.0 (3)
C7—N1—H1N117 (2)C24—C25—H25A108.3
C8—N1—H1N114 (2)C6—C25—H25A108.3
C15—N2—C4120.4 (2)C24—C25—H25B108.3
C19—N3—C22121.6 (2)C6—C25—H25B108.3
C19—N3—C23120.9 (2)H25A—C25—H25B107.4
C22—N3—C23117.5 (2)C27—C26—C30126.9 (2)
C32—N4—C33127.6 (2)C27—C26—S2112.1 (2)
C32—N4—H4N118 (2)C30—C26—S2120.93 (19)
C33—N4—H4N114 (2)C26—C27—C28112.6 (2)
C40—N5—C29120.6 (2)C26—C27—C31120.0 (2)
C44—N6—C48120.9 (2)C28—C27—C31127.2 (2)
C44—N6—C47121.1 (2)C29—C28—C27112.4 (2)
C48—N6—C47117.4 (2)C29—C28—C32125.6 (2)
C2—C1—C5126.3 (2)C27—C28—C32122.0 (2)
C2—C1—S1112.79 (19)C28—C29—N5126.4 (2)
C5—C1—S1120.88 (19)C28—C29—S2110.94 (19)
C1—C2—C3112.2 (2)N5—C29—S2122.64 (19)
C1—C2—C6120.6 (2)C26—C30—C50110.3 (2)
C3—C2—C6127.1 (2)C26—C30—H30A109.6
C4—C3—C2112.1 (2)C50—C30—H30A109.6
C4—C3—C7126.2 (2)C26—C30—H30B109.6
C2—C3—C7121.7 (2)C50—C30—H30B109.6
C3—C4—N2126.0 (2)H30A—C30—H30B108.1
C3—C4—S1111.02 (19)C27—C31—C49110.8 (2)
N2—C4—S1122.97 (18)C27—C31—H31A109.5
C1—C5—C24109.2 (2)C49—C31—H31A109.5
C1—C5—H5A109.8C27—C31—H31B109.5
C24—C5—H5A109.8C49—C31—H31B109.5
C1—C5—H5B109.8H31A—C31—H31B108.1
C24—C5—H5B109.8O2—C32—N4122.6 (2)
H5A—C5—H5B108.3O2—C32—C28121.6 (2)
C2—C6—C25112.5 (2)N4—C32—C28115.9 (2)
C2—C6—H6A109.1C34—C33—C38118.1 (2)
C25—C6—H6A109.1C34—C33—N4119.0 (2)
C2—C6—H6B109.1C38—C33—N4122.8 (2)
C25—C6—H6B109.1C35—C34—C33121.1 (3)
H6A—C6—H6B107.8C35—C34—H34119.5
O1—C7—N1122.5 (2)C33—C34—H34119.5
O1—C7—C3120.9 (2)C34—C35—C36121.5 (3)
N1—C7—C3116.6 (2)C34—C35—H35119.2
C9—C8—C13117.4 (2)C36—C35—H35119.2
C9—C8—N1118.5 (2)C37—C36—C35116.7 (3)
C13—C8—N1124.0 (2)C37—C36—C39121.5 (3)
C8—C9—C10121.4 (3)C35—C36—C39121.7 (3)
C8—C9—H9119.3C38—C37—C36122.8 (3)
C10—C9—H9119.3C38—C37—H37118.6
C11—C10—C9121.9 (3)C36—C37—H37118.6
C11—C10—H10119.1C37—C38—C33119.7 (3)
C9—C10—H10119.1C37—C38—H38120.1
C12—C11—C10116.3 (2)C33—C38—H38120.1
C12—C11—C14122.2 (3)C36—C39—H39A109.5
C10—C11—C14121.5 (3)C36—C39—H39B109.5
C11—C12—C13122.9 (3)H39A—C39—H39B109.5
C11—C12—H12118.5C36—C39—H39C109.5
C13—C12—H12118.5H39A—C39—H39C109.5
C8—C13—C12120.1 (3)H39B—C39—H39C109.5
C8—C13—H13120.0N5—C40—C41124.8 (3)
C12—C13—H13120.0N5—C40—H40117.6
C11—C14—H14A109.5C41—C40—H40117.6
C11—C14—H14B109.5C46—C41—C42117.0 (2)
H14A—C14—H14B109.5C46—C41—C40119.7 (3)
C11—C14—H14C109.5C42—C41—C40123.2 (2)
H14A—C14—H14C109.5C43—C42—C41121.8 (2)
H14B—C14—H14C109.5C43—C42—H42119.1
N2—C15—C16124.7 (2)C41—C42—H42119.1
N2—C15—H15117.6C42—C43—C44121.5 (3)
C16—C15—H15117.6C42—C43—H43119.3
C17—C16—C21116.7 (2)C44—C43—H43119.3
C17—C16—C15120.2 (2)N6—C44—C45121.8 (2)
C21—C16—C15123.0 (2)N6—C44—C43121.7 (2)
C18—C17—C16122.4 (3)C45—C44—C43116.6 (2)
C18—C17—H17118.8C46—C45—C44121.0 (2)
C16—C17—H17118.8C46—C45—H45119.5
C17—C18—C19120.7 (2)C44—C45—H45119.5
C17—C18—H18119.7C45—C46—C41122.1 (3)
C19—C18—H18119.7C45—C46—H46119.0
N3—C19—C18121.7 (2)C41—C46—H46119.0
N3—C19—C20121.3 (2)N6—C47—H47A109.5
C18—C19—C20117.0 (2)N6—C47—H47B109.5
C21—C20—C19121.4 (2)H47A—C47—H47B109.5
C21—C20—H20119.3N6—C47—H47C109.5
C19—C20—H20119.3H47A—C47—H47C109.5
C20—C21—C16121.8 (2)H47B—C47—H47C109.5
C20—C21—H21119.1N6—C48—H48A109.5
C16—C21—H21119.1N6—C48—H48B109.5
N3—C22—H22A109.5H48A—C48—H48B109.5
N3—C22—H22B109.5N6—C48—H48C109.5
H22A—C22—H22B109.5H48A—C48—H48C109.5
N3—C22—H22C109.5H48B—C48—H48C109.5
H22A—C22—H22C109.5C50—C49—C31112.6 (3)
H22B—C22—H22C109.5C50—C49—H49A109.1
N3—C23—H23A109.5C31—C49—H49A109.1
N3—C23—H23B109.5C50—C49—H49B109.1
H23A—C23—H23B109.5C31—C49—H49B109.1
N3—C23—H23C109.5H49A—C49—H49B107.8
H23A—C23—H23C109.5C49—C50—C30111.6 (3)
H23B—C23—H23C109.5C49—C50—H50A109.3
C25—C24—C5113.4 (3)C30—C50—H50A109.3
C25—C24—H24A108.9C49—C50—H50B109.3
C5—C24—H24A108.9C30—C50—H50B109.3
C25—C24—H24B108.9H50A—C50—H50B108.0
C4—S1—C1—C20.1 (2)C29—S2—C26—C270.2 (2)
C4—S1—C1—C5179.2 (2)C29—S2—C26—C30178.2 (2)
C5—C1—C2—C3179.2 (2)C30—C26—C27—C28178.1 (2)
S1—C1—C2—C30.2 (3)S2—C26—C27—C280.3 (3)
C5—C1—C2—C61.7 (4)C30—C26—C27—C310.9 (4)
S1—C1—C2—C6177.36 (19)S2—C26—C27—C31177.0 (2)
C1—C2—C3—C40.2 (3)C26—C27—C28—C290.2 (3)
C6—C2—C3—C4177.1 (2)C31—C27—C28—C29176.8 (2)
C1—C2—C3—C7179.8 (2)C26—C27—C28—C32179.8 (2)
C6—C2—C3—C72.4 (4)C31—C27—C28—C323.2 (4)
C2—C3—C4—N2180.0 (2)C27—C28—C29—N5178.0 (2)
C7—C3—C4—N20.5 (4)C32—C28—C29—N52.0 (4)
C2—C3—C4—S10.2 (3)C27—C28—C29—S20.0 (3)
C7—C3—C4—S1179.69 (19)C32—C28—C29—S2180.0 (2)
C15—N2—C4—C3175.3 (2)C40—N5—C29—C28175.3 (3)
C15—N2—C4—S14.9 (3)C40—N5—C29—S26.9 (3)
C1—S1—C4—C30.07 (19)C26—S2—C29—C280.1 (2)
C1—S1—C4—N2179.9 (2)C26—S2—C29—N5178.2 (2)
C2—C1—C5—C2418.2 (4)C27—C26—C30—C5010.4 (4)
S1—C1—C5—C24160.8 (2)S2—C26—C30—C50171.9 (2)
C1—C2—C6—C259.5 (4)C26—C27—C31—C4917.6 (4)
C3—C2—C6—C25173.3 (3)C28—C27—C31—C49159.2 (3)
C8—N1—C7—O12.1 (4)C33—N4—C32—O23.2 (4)
C8—N1—C7—C3177.5 (2)C33—N4—C32—C28176.6 (2)
C4—C3—C7—O1179.5 (3)C29—C28—C32—O2171.8 (3)
C2—C3—C7—O10.0 (4)C27—C28—C32—O28.2 (4)
C4—C3—C7—N10.1 (4)C29—C28—C32—N48.3 (4)
C2—C3—C7—N1179.6 (2)C27—C28—C32—N4171.7 (2)
C7—N1—C8—C9179.0 (3)C32—N4—C33—C34151.6 (3)
C7—N1—C8—C130.9 (4)C32—N4—C33—C3831.5 (4)
C13—C8—C9—C100.8 (4)C38—C33—C34—C351.6 (4)
N1—C8—C9—C10179.1 (3)N4—C33—C34—C35175.4 (2)
C8—C9—C10—C110.0 (5)C33—C34—C35—C360.3 (4)
C9—C10—C11—C120.8 (5)C34—C35—C36—C372.3 (4)
C9—C10—C11—C14177.1 (3)C34—C35—C36—C39178.4 (3)
C10—C11—C12—C130.9 (5)C35—C36—C37—C382.3 (4)
C14—C11—C12—C13177.0 (3)C39—C36—C37—C38178.4 (3)
C9—C8—C13—C120.7 (4)C36—C37—C38—C330.4 (4)
N1—C8—C13—C12179.2 (3)C34—C33—C38—C371.6 (4)
C11—C12—C13—C80.1 (5)N4—C33—C38—C37175.3 (3)
C4—N2—C15—C16179.9 (2)C29—N5—C40—C41175.8 (2)
N2—C15—C16—C17176.3 (3)N5—C40—C41—C46177.6 (3)
N2—C15—C16—C211.3 (4)N5—C40—C41—C420.3 (4)
C21—C16—C17—C180.5 (4)C46—C41—C42—C430.1 (4)
C15—C16—C17—C18178.2 (3)C40—C41—C42—C43177.9 (3)
C16—C17—C18—C190.0 (4)C41—C42—C43—C440.5 (4)
C22—N3—C19—C18179.5 (3)C48—N6—C44—C451.4 (4)
C23—N3—C19—C180.3 (4)C47—N6—C44—C45173.2 (3)
C22—N3—C19—C200.9 (4)C48—N6—C44—C43179.2 (3)
C23—N3—C19—C20179.3 (3)C47—N6—C44—C437.4 (4)
C17—C18—C19—N3179.1 (3)C42—C43—C44—N6178.9 (3)
C17—C18—C19—C200.6 (4)C42—C43—C44—C450.5 (4)
N3—C19—C20—C21179.0 (3)N6—C44—C45—C46179.2 (3)
C18—C19—C20—C210.7 (4)C43—C44—C45—C460.2 (4)
C19—C20—C21—C160.1 (4)C44—C45—C46—C410.2 (4)
C17—C16—C21—C200.4 (4)C42—C41—C46—C450.3 (4)
C15—C16—C21—C20178.1 (3)C40—C41—C46—C45178.3 (3)
C1—C5—C24—C2543.8 (4)C27—C31—C49—C5048.7 (4)
C5—C24—C25—C656.0 (5)C31—C49—C50—C3062.2 (4)
C2—C6—C25—C2436.8 (4)C26—C30—C50—C4940.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···N20.86 (3)2.06 (3)2.780 (3)141 (3)
N4—H4N···N50.82 (3)2.07 (3)2.765 (3)141 (3)

Experimental details

(I)(II)
Crystal data
Chemical formulaC23H25N3OSC25H27N3OS
Mr391.53417.57
Crystal system, space groupTriclinic, P1Monoclinic, P21/n
Temperature (K)293293
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
V3)1020.9 (2)4324 (2)
Z28
Radiation typeMo KαMo Kα
µ (mm1)0.180.17
Crystal size (mm)0.20 × 0.20 × 0.200.40 × 0.35 × 0.30
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Bruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1997)
Multi-scan
(SADABS; Sheldrick, 1997)
Tmin, Tmax0.908, 0.9660.925, 0.950
No. of measured, independent and
observed reflections
10235, 3725, 1678 [I > 2σ(I)]33520, 8756, 6163 [I > \2s(I)]
Rint0.0860.034
(sin θ/λ)max1)0.6020.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.128, 0.94 0.059, 0.165, 1.06
No. of reflections37258756
No. of parameters262555
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.20, 0.190.49, 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).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···N20.77 (3)2.12 (3)2.766 (5)143 (3)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···N20.86 (3)2.06 (3)2.780 (3)141 (3)
N4—H4N···N50.82 (3)2.07 (3)2.765 (3)141 (3)
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds