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In the title mol­ecule, C25H22N2O3S2, the two C—S bond lengths of the thio­phene ring are significantly different, at 1.719 (2) and 1.758 (2) Å. In the crystal structure, mol­ecules form centrosymmetric dimers via inter­molecular N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702377X/lh2388sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680702377X/lh2388Isup2.hkl
Contains datablock I

CCDC reference: 651510

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.043
  • wR factor = 0.108
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

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Alert level B PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.13 Ratio
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 300 Ang. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.83 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT352_ALERT_3_C Short N-H Bond (0.87A) N1 - H1NA ... 0.76 Ang. PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 43.00 A   3 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: All authors made significant contribution in this work. The idea of synthesis belongs to Kovalenko. The synthesis was performed by Vlasenko and Parkhomenko. X-ray diffraction experiment was performed by Baumer. The analysis of diffraction data was performed by Konovalova and Shishkin.

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Comment top

Thiophene is a very important pharmacophore in many biologically active compounds. Thiophene derivatives are used as antibiotics, anaesthetics, antiparasitics, resolvents, antihelmintic drugs, anticholinergic drugs, antiulcer agents, antihistamines, antitussives (Patent USA, 2000, Kovalenko & Victorova, 2005), therefore investigation of their molecular structure may provide useful information for the understanding of mechanisms of biological activity. In this paper we report the molecular and crystal structure of 2-aroyl-3-amino-4-arylsulfonyl-5-arylamino-thiophene (Fig.1). The carbonyl group is essentially coplanar with the thiophene ring (the C1—C4—C5—O3 torsion angle is 3.1 (4)°). Such a conformation of this group is stabilized by the weak intramolecular hydrogen bond N1—H1NA···O3 H···O 2.06 Å, N—H···O 141°. Atoms N1 and N2 have a planar configuration, the sum of the bond angles, centered at these atoms are 360° in both cases. The phenyl substituent at atom C5 atom is rotated with respect to the C4—C5 bond (the C4—C5—C6—C7 torsion angle is -47.9 (3) °). Such orientation of the phenyl ring indicates an interaction between phenyl ring and atom S1 (the short intramolecular contact C7···S1 is 2.71Å [van der Waals radii sum is 3.01 Å; Zefirov & Zorky (1995)]. The phenyl substituent at the S2 atom has an almost orthogonal orientation relative to the thiophene ring (the C20—S2—C2—C3 torsion angle is -84.4 (2) °) and with respect to the C2—S2 bond (the C2—S2—C20—C25 torsion angle is -83.3 (2)°). The conformation of sulfonyl group is stabilized by weak intramolecular hydrogen bonds N1—H1NB···O2 H···O 2.22 Å, N—H···O 124° and N2—H2NA···O1 H···O 2.25 Å, N—H···O 130°, respectively. The dimethylphenylamino substituent adopts an sp-conformation relative to the C3—S1 bond (the S1—C3—N2—C12 torsion angle is -3.9 (4) °) and it is rotated with respect to the C3—N2 bond (the C3—N2—C12—C17 torsion angle is 64.5 (4) °). The most interesting feature of the structure is difference in the S—C bond lengths within thiophene ring. The C4—S1 bond (1.758 (2) Å) is significantly longer than the S1—C3 bond (1.719 (2) Å) and the reported mean value is 1.712 Å (Bürgi & Dunitz, 1994). Comparison of bond lengths within the thiophene ring in the title compound and other 2,5-disubstituted thiophene compounds (Apinitis et al., 1984; Xu et al., 2004) indicates that elongation of the S1—C4 bond is observed when an electron-withdrawing substituent is at atom C4. This may lead to considerable asymmetry in conjugation interactions within the C—S—C fragment of thiophene ring. In the crystal structure, molecules of title compound form centrosymmetric dimers due to intermolecular hydrogen bond N1—H1NB···O2' (symmetry code (') -x + 1, -y + 1, -z + 2) H···O' 2.19 Å, N—H···O' 142 °.

Related literature top

For a comparison of the Csp2—S bond lengths in other related crystal structures, see: Apinitis et al., (1984); Xu et al. (2004).

For related literature, see: Bürgi & Dunitz (1994); Kovalenko & Victorova (2005); Patent (2000); Vlasenko et al. (2005); Zefirov & Zorky (1995).

Experimental top

The title compound was obtained by means of one pot method of synthesis, applying Thorpe-Ziegler-cyclization. The reaction was carried out in the methanol solution of potassium hydroxide (1.99 mmol), in which arylsulfonylacetonitrile (1.66 mmol) and arylisothiocyanate (1.66 mmol) were dissolved. The solution was treated with phenacylbromide (1.99 mmol) and potassium hydroxide (1.99 mmol). At reation completion the solid was acidified using mineral acid. Crystals for X-ray diffraction study were obtained by evaporation of methanol -dimethyl formamide solution (Vlasenko et al., 2005).

Refinement top

All hydrogen atoms were located from electron density difference maps but were included in the refinement in the riding motion approximation with C—H = 0.93–0.96Å and Uiso constrained to be 1.5 times the Ueq of the carrier atom for the methyl groups and 1.2 times Ueq of the carrier atom for the other atoms. The hydrogen atoms which are take part in the formation of hydrogen bonds were refined isotropically.

Structure description top

Thiophene is a very important pharmacophore in many biologically active compounds. Thiophene derivatives are used as antibiotics, anaesthetics, antiparasitics, resolvents, antihelmintic drugs, anticholinergic drugs, antiulcer agents, antihistamines, antitussives (Patent USA, 2000, Kovalenko & Victorova, 2005), therefore investigation of their molecular structure may provide useful information for the understanding of mechanisms of biological activity. In this paper we report the molecular and crystal structure of 2-aroyl-3-amino-4-arylsulfonyl-5-arylamino-thiophene (Fig.1). The carbonyl group is essentially coplanar with the thiophene ring (the C1—C4—C5—O3 torsion angle is 3.1 (4)°). Such a conformation of this group is stabilized by the weak intramolecular hydrogen bond N1—H1NA···O3 H···O 2.06 Å, N—H···O 141°. Atoms N1 and N2 have a planar configuration, the sum of the bond angles, centered at these atoms are 360° in both cases. The phenyl substituent at atom C5 atom is rotated with respect to the C4—C5 bond (the C4—C5—C6—C7 torsion angle is -47.9 (3) °). Such orientation of the phenyl ring indicates an interaction between phenyl ring and atom S1 (the short intramolecular contact C7···S1 is 2.71Å [van der Waals radii sum is 3.01 Å; Zefirov & Zorky (1995)]. The phenyl substituent at the S2 atom has an almost orthogonal orientation relative to the thiophene ring (the C20—S2—C2—C3 torsion angle is -84.4 (2) °) and with respect to the C2—S2 bond (the C2—S2—C20—C25 torsion angle is -83.3 (2)°). The conformation of sulfonyl group is stabilized by weak intramolecular hydrogen bonds N1—H1NB···O2 H···O 2.22 Å, N—H···O 124° and N2—H2NA···O1 H···O 2.25 Å, N—H···O 130°, respectively. The dimethylphenylamino substituent adopts an sp-conformation relative to the C3—S1 bond (the S1—C3—N2—C12 torsion angle is -3.9 (4) °) and it is rotated with respect to the C3—N2 bond (the C3—N2—C12—C17 torsion angle is 64.5 (4) °). The most interesting feature of the structure is difference in the S—C bond lengths within thiophene ring. The C4—S1 bond (1.758 (2) Å) is significantly longer than the S1—C3 bond (1.719 (2) Å) and the reported mean value is 1.712 Å (Bürgi & Dunitz, 1994). Comparison of bond lengths within the thiophene ring in the title compound and other 2,5-disubstituted thiophene compounds (Apinitis et al., 1984; Xu et al., 2004) indicates that elongation of the S1—C4 bond is observed when an electron-withdrawing substituent is at atom C4. This may lead to considerable asymmetry in conjugation interactions within the C—S—C fragment of thiophene ring. In the crystal structure, molecules of title compound form centrosymmetric dimers due to intermolecular hydrogen bond N1—H1NB···O2' (symmetry code (') -x + 1, -y + 1, -z + 2) H···O' 2.19 Å, N—H···O' 142 °.

For a comparison of the Csp2—S bond lengths in other related crystal structures, see: Apinitis et al., (1984); Xu et al. (2004).

For related literature, see: Bürgi & Dunitz (1994); Kovalenko & Victorova (2005); Patent (2000); Vlasenko et al. (2005); Zefirov & Zorky (1995).

Computing details top

Data collection: P3 (Siemens,1989); cell refinement: P3; data reduction: XDISK (Siemens, 1991); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of the molecular structure of (I) with atomic numbering. All atoms are shown with displacement ellipsoids drawn at the 50% probability level.
[3-Amino-5-(3,5-dimethylanilino)-4-phenylsulfonyl-2-thienyl]phenylmethanone top
Crystal data top
C25H22N2O3S2Z = 2
Mr = 462.57F(000) = 484
Triclinic, P1Dx = 1.296 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.497 (3) ÅCell parameters from 36 reflections
b = 11.451 (3) Åθ = 8–22°
c = 11.863 (3) ŵ = 0.25 mm1
α = 65.65 (2)°T = 293 K
β = 69.654 (19)°Block, colourless
γ = 70.18 (2)°0.40 × 0.20 × 0.20 mm
V = 1185.6 (6) Å3
Data collection top
Siemens P3/PC
diffractometer
3150 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
Detector resolution: 16.1827 pixels mm-1h = 1112
θ–2θ scansk = 1213
4246 measured reflectionsl = 1314
4042 independent reflections
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)] = 0.043Hydrogen site location: difference Fourier map
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0604P)2 + 0.2736P]
where P = (Fo2 + 2Fc2)/3
4042 reflections(Δ/σ)max = 0.001
322 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
C25H22N2O3S2γ = 70.18 (2)°
Mr = 462.57V = 1185.6 (6) Å3
Triclinic, P1Z = 2
a = 10.497 (3) ÅMo Kα radiation
b = 11.451 (3) ŵ = 0.25 mm1
c = 11.863 (3) ÅT = 293 K
α = 65.65 (2)°0.40 × 0.20 × 0.20 mm
β = 69.654 (19)°
Data collection top
Siemens P3/PC
diffractometer
3150 reflections with I > 2σ(I)
4246 measured reflectionsRint = 0.048
4042 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.25 e Å3
4042 reflectionsΔρmin = 0.31 e Å3
322 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
S10.47589 (6)0.72106 (6)0.46973 (5)0.04259 (18)
S20.30992 (6)0.69038 (6)0.85957 (5)0.03452 (16)
N10.6086 (3)0.5073 (2)0.7787 (2)0.0498 (6)
H1NA0.681 (3)0.473 (3)0.750 (3)0.046 (8)*
H1NB0.575 (3)0.501 (3)0.866 (3)0.070 (9)*
N20.2320 (2)0.8339 (2)0.5927 (2)0.0473 (6)
H2NA0.177 (3)0.849 (3)0.653 (3)0.047 (8)*
O10.16388 (16)0.73500 (19)0.86151 (15)0.0497 (5)
O20.35524 (18)0.57316 (16)0.95816 (14)0.0443 (4)
O30.81054 (17)0.46304 (18)0.57554 (16)0.0525 (5)
C10.5382 (2)0.5893 (2)0.6897 (2)0.0329 (5)
C20.4011 (2)0.6711 (2)0.71376 (19)0.0332 (5)
C30.3543 (2)0.7472 (2)0.6033 (2)0.0350 (5)
C40.5941 (2)0.6049 (2)0.5602 (2)0.0355 (5)
C50.7306 (2)0.5429 (2)0.5067 (2)0.0365 (5)
C60.7839 (2)0.5752 (2)0.3652 (2)0.0347 (5)
C70.7075 (3)0.5789 (2)0.2888 (2)0.0420 (6)
H70.61750.56510.32440.052 (8)*
C80.7649 (3)0.6031 (3)0.1598 (2)0.0517 (7)
H80.71400.60380.10910.051 (7)*
C90.8971 (3)0.6262 (3)0.1057 (3)0.0547 (7)
H90.93470.64400.01840.067 (9)*
C100.9727 (3)0.6230 (3)0.1805 (3)0.0551 (7)
H101.06190.63880.14390.056 (8)*
C110.9177 (3)0.5966 (2)0.3100 (2)0.0466 (6)
H110.97060.59310.36050.064 (9)*
C120.1956 (2)0.9153 (2)0.4746 (2)0.0398 (6)
C130.1705 (3)1.0494 (3)0.4418 (3)0.0490 (6)
H130.18021.08540.49500.057 (8)*
C140.1303 (3)1.1318 (3)0.3284 (3)0.0559 (7)
C150.1194 (3)1.0741 (3)0.2517 (2)0.0522 (7)
H150.09261.12810.17620.090 (11)*
C160.1467 (3)0.9397 (3)0.2822 (2)0.0484 (6)
C170.1831 (3)0.8601 (3)0.3971 (2)0.0447 (6)
H170.19890.76910.42150.056 (8)*
C180.1001 (5)1.2791 (3)0.2929 (4)0.0915 (12)
H18B0.06761.30210.36900.17 (2)*
H18A0.02971.31980.24540.132 (17)*
H18C0.18381.30930.24180.17 (2)*
C190.1363 (5)0.8786 (4)0.1955 (4)0.0811 (11)
H19A0.09810.94640.12690.16 (2)*
H19C0.07650.81780.24320.19 (3)*
H19B0.22750.83260.16150.144 (19)*
C200.3623 (3)0.8199 (2)0.8620 (2)0.0411 (6)
C210.2846 (4)0.9460 (3)0.8255 (3)0.0666 (9)
H210.20150.96350.80380.086 (11)*
C220.3316 (6)1.0473 (4)0.8215 (4)0.0931 (13)
H220.27941.13340.79720.125 (16)*
C230.4522 (6)1.0221 (4)0.8525 (4)0.0916 (13)
H230.48381.09120.84730.116 (14)*
C240.5291 (4)0.8953 (4)0.8917 (4)0.0811 (10)
H240.61130.87880.91460.103 (13)*
C250.4848 (3)0.7929 (3)0.8970 (3)0.0599 (8)
H250.53620.70680.92370.071 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0381 (3)0.0532 (4)0.0214 (3)0.0055 (3)0.0114 (2)0.0074 (3)
S20.0337 (3)0.0432 (3)0.0204 (3)0.0070 (2)0.0074 (2)0.0055 (2)
N10.0429 (14)0.0621 (15)0.0295 (12)0.0092 (11)0.0175 (10)0.0107 (11)
N20.0400 (12)0.0579 (14)0.0252 (10)0.0110 (10)0.0115 (9)0.0107 (10)
O10.0325 (9)0.0755 (13)0.0309 (9)0.0087 (8)0.0057 (7)0.0127 (9)
O20.0539 (10)0.0470 (10)0.0246 (8)0.0116 (8)0.0145 (7)0.0010 (7)
O30.0383 (10)0.0603 (11)0.0418 (10)0.0065 (8)0.0169 (8)0.0092 (9)
C10.0341 (12)0.0349 (12)0.0264 (11)0.0047 (9)0.0127 (9)0.0051 (9)
C20.0373 (12)0.0362 (12)0.0232 (11)0.0057 (9)0.0117 (9)0.0057 (9)
C30.0357 (12)0.0400 (12)0.0248 (11)0.0035 (10)0.0101 (9)0.0083 (10)
C40.0336 (12)0.0413 (13)0.0265 (11)0.0012 (10)0.0132 (9)0.0076 (10)
C50.0343 (12)0.0382 (12)0.0351 (12)0.0048 (10)0.0123 (10)0.0098 (10)
C60.0342 (12)0.0315 (11)0.0336 (12)0.0039 (9)0.0065 (10)0.0105 (10)
C70.0418 (14)0.0473 (14)0.0403 (13)0.0136 (11)0.0067 (11)0.0180 (11)
C80.0677 (18)0.0548 (16)0.0406 (14)0.0151 (13)0.0179 (13)0.0185 (13)
C90.0657 (18)0.0517 (16)0.0369 (15)0.0149 (14)0.0010 (13)0.0135 (12)
C100.0426 (15)0.0651 (18)0.0445 (15)0.0172 (13)0.0035 (12)0.0135 (14)
C110.0368 (13)0.0521 (15)0.0470 (15)0.0066 (11)0.0096 (11)0.0161 (12)
C120.0317 (12)0.0470 (14)0.0269 (11)0.0058 (10)0.0112 (9)0.0078 (10)
C130.0435 (14)0.0503 (15)0.0478 (15)0.0006 (11)0.0157 (12)0.0164 (13)
C140.0486 (16)0.0439 (15)0.0528 (17)0.0011 (12)0.0166 (13)0.0006 (13)
C150.0424 (14)0.0574 (17)0.0352 (14)0.0009 (12)0.0178 (11)0.0020 (13)
C160.0403 (14)0.0619 (17)0.0349 (13)0.0016 (12)0.0154 (11)0.0112 (12)
C170.0422 (14)0.0439 (14)0.0363 (13)0.0034 (11)0.0148 (11)0.0083 (11)
C180.111 (3)0.0471 (19)0.096 (3)0.003 (2)0.042 (3)0.0024 (19)
C190.096 (3)0.096 (3)0.063 (2)0.008 (2)0.042 (2)0.030 (2)
C200.0474 (14)0.0486 (14)0.0244 (11)0.0107 (11)0.0053 (10)0.0125 (10)
C210.091 (2)0.0486 (17)0.0590 (19)0.0016 (15)0.0334 (17)0.0154 (14)
C220.158 (4)0.048 (2)0.072 (2)0.020 (2)0.039 (3)0.0120 (17)
C230.146 (4)0.085 (3)0.060 (2)0.068 (3)0.006 (2)0.022 (2)
C240.079 (2)0.103 (3)0.084 (3)0.044 (2)0.008 (2)0.044 (2)
C250.0550 (17)0.071 (2)0.0635 (19)0.0158 (15)0.0109 (15)0.0333 (16)
Geometric parameters (Å, º) top
S1—C31.719 (2)C12—C171.371 (3)
S1—C41.758 (2)C12—C131.372 (4)
S2—O21.4337 (17)C13—C141.399 (4)
S2—O11.4372 (17)C13—H130.9300
S2—C21.726 (2)C14—C151.377 (4)
S2—C201.761 (3)C14—C181.506 (4)
N1—C11.340 (3)C15—C161.376 (4)
N1—H1NA0.76 (3)C15—H150.9300
N1—H1NB0.95 (3)C16—C171.391 (3)
N2—C31.340 (3)C16—C191.511 (4)
N2—C121.425 (3)C17—H170.9300
N2—H2NA0.78 (3)C18—H18B0.9600
O3—C51.244 (3)C18—H18A0.9600
C1—C41.398 (3)C18—H18C0.9600
C1—C21.432 (3)C19—H19A0.9600
C2—C31.391 (3)C19—H19C0.9600
C4—C51.418 (3)C19—H19B0.9600
C5—C61.497 (3)C20—C211.367 (4)
C6—C71.385 (3)C20—C251.385 (4)
C6—C111.386 (3)C21—C221.384 (5)
C7—C81.380 (3)C21—H210.9300
C7—H70.9300C22—C231.345 (6)
C8—C91.378 (4)C22—H220.9300
C8—H80.9300C23—C241.373 (6)
C9—C101.365 (4)C23—H230.9300
C9—H90.9300C24—C251.372 (4)
C10—C111.380 (4)C24—H240.9300
C10—H100.9300C25—H250.9300
C11—H110.9300
C3—S1—C492.08 (11)C17—C12—N2120.3 (2)
O2—S2—O1118.85 (11)C13—C12—N2118.6 (2)
O2—S2—C2108.58 (11)C12—C13—C14119.8 (3)
O1—S2—C2108.25 (10)C12—C13—H13120.1
O2—S2—C20107.97 (11)C14—C13—H13120.1
O1—S2—C20107.25 (12)C15—C14—C13118.1 (3)
C2—S2—C20105.11 (11)C15—C14—C18121.7 (3)
C1—N1—H1NA112 (2)C13—C14—C18120.2 (3)
C1—N1—H1NB123.6 (19)C16—C15—C14122.7 (2)
H1NA—N1—H1NB124 (3)C16—C15—H15118.6
C3—N2—C12124.4 (2)C14—C15—H15118.6
C3—N2—H2NA121 (2)C15—C16—C17118.0 (2)
C12—N2—H2NA114 (2)C15—C16—C19121.8 (3)
N1—C1—C4122.4 (2)C17—C16—C19120.2 (3)
N1—C1—C2125.2 (2)C12—C17—C16120.3 (2)
C4—C1—C2112.35 (18)C12—C17—H17119.9
C3—C2—C1112.82 (19)C16—C17—H17119.9
C3—C2—S2122.23 (17)C14—C18—H18B109.5
C1—C2—S2124.52 (16)C14—C18—H18A109.5
N2—C3—C2127.8 (2)H18B—C18—H18A109.5
N2—C3—S1120.20 (17)C14—C18—H18C109.5
C2—C3—S1112.01 (16)H18B—C18—H18C109.5
C1—C4—C5125.2 (2)H18A—C18—H18C109.5
C1—C4—S1110.74 (16)C16—C19—H19A109.5
C5—C4—S1123.93 (17)C16—C19—H19C109.5
O3—C5—C4121.0 (2)H19A—C19—H19C109.5
O3—C5—C6118.2 (2)C16—C19—H19B109.5
C4—C5—C6120.7 (2)H19A—C19—H19B109.5
C7—C6—C11119.0 (2)H19C—C19—H19B109.5
C7—C6—C5122.7 (2)C21—C20—C25120.7 (3)
C11—C6—C5118.2 (2)C21—C20—S2120.0 (2)
C8—C7—C6120.0 (2)C25—C20—S2119.3 (2)
C8—C7—H7120.0C20—C21—C22119.1 (3)
C6—C7—H7120.0C20—C21—H21120.5
C9—C8—C7120.4 (2)C22—C21—H21120.5
C9—C8—H8119.8C23—C22—C21120.5 (4)
C7—C8—H8119.8C23—C22—H22119.8
C10—C9—C8119.8 (2)C21—C22—H22119.8
C10—C9—H9120.1C22—C23—C24120.7 (4)
C8—C9—H9120.1C22—C23—H23119.7
C9—C10—C11120.4 (3)C24—C23—H23119.7
C9—C10—H10119.8C25—C24—C23120.1 (4)
C11—C10—H10119.8C25—C24—H24120.0
C10—C11—C6120.3 (2)C23—C24—H24120.0
C10—C11—H11119.9C24—C25—C20118.9 (3)
C6—C11—H11119.9C24—C25—H25120.5
C17—C12—C13121.0 (2)C20—C25—H25120.5
N1—C1—C2—C3179.4 (2)C6—C7—C8—C91.3 (4)
C4—C1—C2—C30.2 (3)C7—C8—C9—C101.1 (4)
N1—C1—C2—S26.8 (4)C8—C9—C10—C110.1 (4)
C4—C1—C2—S2172.34 (17)C9—C10—C11—C61.1 (4)
O2—S2—C2—C3160.23 (19)C7—C6—C11—C100.9 (4)
O1—S2—C2—C329.9 (2)C5—C6—C11—C10178.2 (2)
C20—S2—C2—C384.4 (2)C3—N2—C12—C1764.5 (4)
O2—S2—C2—C127.9 (2)C3—N2—C12—C13116.9 (3)
O1—S2—C2—C1158.18 (19)C17—C12—C13—C140.6 (4)
C20—S2—C2—C187.5 (2)N2—C12—C13—C14178.0 (2)
C12—N2—C3—C2175.3 (2)C12—C13—C14—C151.0 (4)
C12—N2—C3—S13.9 (4)C12—C13—C14—C18178.9 (3)
C1—C2—C3—N2179.6 (2)C13—C14—C15—C160.1 (4)
S2—C2—C3—N26.9 (4)C18—C14—C15—C16179.9 (3)
C1—C2—C3—S10.3 (3)C14—C15—C16—C171.7 (4)
S2—C2—C3—S1172.41 (13)C14—C15—C16—C19179.0 (3)
C4—S1—C3—N2179.6 (2)C13—C12—C17—C161.1 (4)
C4—S1—C3—C20.29 (19)N2—C12—C17—C16179.6 (2)
N1—C1—C4—C53.0 (4)C15—C16—C17—C122.2 (4)
C2—C1—C4—C5176.2 (2)C19—C16—C17—C12178.6 (3)
N1—C1—C4—S1179.2 (2)O2—S2—C20—C21149.6 (2)
C2—C1—C4—S10.0 (3)O1—S2—C20—C2120.4 (2)
C3—S1—C4—C10.16 (19)C2—S2—C20—C2194.6 (2)
C3—S1—C4—C5176.4 (2)O2—S2—C20—C2532.5 (2)
C1—C4—C5—O33.1 (4)O1—S2—C20—C25161.7 (2)
S1—C4—C5—O3178.77 (19)C2—S2—C20—C2583.3 (2)
C1—C4—C5—C6175.0 (2)C25—C20—C21—C221.3 (4)
S1—C4—C5—C60.7 (3)S2—C20—C21—C22176.5 (3)
O3—C5—C6—C7134.0 (2)C20—C21—C22—C230.3 (6)
C4—C5—C6—C747.9 (3)C21—C22—C23—C241.6 (6)
O3—C5—C6—C1143.2 (3)C22—C23—C24—C251.4 (6)
C4—C5—C6—C11134.9 (2)C23—C24—C25—C200.2 (5)
C11—C6—C7—C80.3 (4)C21—C20—C25—C241.6 (4)
C5—C6—C7—C8176.9 (2)S2—C20—C25—C24176.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1NA···O30.76 (3)2.06 (3)2.699 (3)141 (3)
N1—H1NB···O20.95 (3)2.22 (3)2.864 (3)124 (2)
N2—H2NA···O10.78 (3)2.25 (3)2.820 (3)130 (2)
N1—H1NB···O2i0.95 (3)2.19 (3)2.993 (3)142 (3)
Symmetry code: (i) x+1, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC25H22N2O3S2
Mr462.57
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)10.497 (3), 11.451 (3), 11.863 (3)
α, β, γ (°)65.65 (2), 69.654 (19), 70.18 (2)
V3)1185.6 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.40 × 0.20 × 0.20
Data collection
DiffractometerSiemens P3/PC
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4246, 4042, 3150
Rint0.048
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.108, 1.02
No. of reflections4042
No. of parameters322
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.25, 0.31

Computer programs: P3 (Siemens,1989), P3, XDISK (Siemens, 1991), SHELXTL (Sheldrick, 1998), SHELXTL.

Selected bond lengths (Å) top
S1—C31.719 (2)S2—O11.4372 (17)
S1—C41.758 (2)S2—C21.726 (2)
S2—O21.4337 (17)S2—C201.761 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1NA···O30.76 (3)2.06 (3)2.699 (3)141 (3)
N1—H1NB···O20.95 (3)2.22 (3)2.864 (3)124 (2)
N2—H2NA···O10.78 (3)2.25 (3)2.820 (3)130 (2)
N1—H1NB···O2i0.95 (3)2.19 (3)2.993 (3)142 (3)
Symmetry code: (i) x+1, y+1, z+2.
 

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