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The title compound, C15H14N2O3S, a potent new bioactive mol­ecule which contains pyrazole and pyrone ring systems, was synthesized by the reaction of benzohydrazide and 3-[bis­(methyl­sulfan­yl)methyl­ene]dihydro-6-methyl-3H-pyran-[2,4-dione in ethanol.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025547/ww6380sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025547/ww6380Isup2.hkl
Contains datablock I

CCDC reference: 287752

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.033
  • wR factor = 0.083
  • Data-to-parameter ratio = 10.4

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.725 1.000 Tmin(prime) and Tmax expected: 0.915 0.977 RR(prime) = 0.774 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.77 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.03 From the CIF: _reflns_number_total 3972 Count of symmetry unique reflns 2618 Completeness (_total/calc) 151.72% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1354 Fraction of Friedel pairs measured 0.517 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

In recent years, there have been a few reports of pyrones derivatives. Some patents reported pyrandione derivatives inhibiting activity for HIV proteinase (Ellsworch & Lunney, 1995; Thaisrivongs & Yang, 1994). Some bioactivities, such as antitobacco viral activity, plant-growth regulation activity, fungicidal and herbicidal bioactivities, have also been reported (Wang et al., 2000; Li et al., 2004). Significant activities against Biomphalaria glabrata egg masses have been reported (de Souza et al., 2004). In view of these facts and in continuation of our interest in the chemistry of heterocycles, we have attempted to synthesize a series of pyranonopyrazole derivatives, one of which, (I), is reported here.

The molecular structure of (I) is shown in Fig. 1. The X-ray analysis reveals that there are two independent molecules which have different orientations in the asymmetric unit.

Experimental top

The title compound was synthesized by adding benzohydrazide (0.136 g, 1 mmol) to an absolute ethanol solution (30 ml) containing 3-[bis(methylsulfanyl)methylene]dihydro-6-methyl-3H-pyran-2,4-dione (0.232 g, 1 mmol). The mixture was stirred for 5.5 h at room temperature. The product was obtained by silica-gel column chromatography using a 1:5 mixture of ethyl acetate and petroleum ether as eluant. Colourless single crystals suitable for X-ray diffraction analysis were obtained by diffusion of n-hexane into a solution of the crude product in dichloromethane. 1H NMR (CDCl3): δ 7.49–8.16 (m, 5H), 4.73–4.80 (m, 1H), 3.15–3.69 (m, 2H), 2.53 (s, 3H), 1.58 (d, 3H, J = 6.3 Hz); 13C NMR (CDCl3): δ 166.72, 161.28, 153.22, 151.45, 133.52, 131.63, 130.97, 127.98, 110.90, 75.36, 31.25, 30.88, 20.54, 13.28; elemental analysis calculated for C15H16N2O2S: C 59.59, H 4.67, N 9.27%; found: C 59.56, H 4.61, N 9.26%.

Refinement top

All H atoms were placed in calculated positions [C—H = 0.93, 0.96, 0.97 or 0.98 Å for phenyl, methyl, methylene and methine H atoms, respectively] and included in the refinement using a riding model, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of (I), with displacement ellipsoids drawn at the 30% probability level.
1-Benzoyl-6-methyl-3-methylsulfanyl-6,7-dihydro-1H-pyrano[4,3-c]pyrazol-4-one top
Crystal data top
C15H14N2O3SF(000) = 1264
Mr = 302.35Dx = 1.354 Mg m3
Monoclinic, CcMelting point: 409 K
Hall symbol: C -2ycMo Kα radiation, λ = 0.71073 Å
a = 24.083 (3) ÅCell parameters from 2146 reflections
b = 7.393 (1) Åθ = 2.3–23.6°
c = 18.820 (3) ŵ = 0.23 mm1
β = 117.765 (2)°T = 293 K
V = 2965.2 (7) Å3Block, colourless
Z = 80.38 × 0.20 × 0.10 mm
Data collection top
Bruker APEX-II CCD area-detector
diffractometer
3972 independent reflections
Radiation source: fine-focus sealed tube3298 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
ϕ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2828
Tmin = 0.725, Tmax = 1.000k = 88
7700 measured reflectionsl = 2220
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.083 w = 1/[σ2(Fo2) + (0.0203P)2 + 0.9288P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3972 reflectionsΔρmax = 0.16 e Å3
383 parametersΔρmin = 0.15 e Å3
2 restraintsAbsolute structure: Flack (1983), 436 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (7)
Crystal data top
C15H14N2O3SV = 2965.2 (7) Å3
Mr = 302.35Z = 8
Monoclinic, CcMo Kα radiation
a = 24.083 (3) ŵ = 0.23 mm1
b = 7.393 (1) ÅT = 293 K
c = 18.820 (3) Å0.38 × 0.20 × 0.10 mm
β = 117.765 (2)°
Data collection top
Bruker APEX-II CCD area-detector
diffractometer
3972 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3298 reflections with I > 2σ(I)
Tmin = 0.725, Tmax = 1.000Rint = 0.020
7700 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.083Δρmax = 0.16 e Å3
S = 1.04Δρmin = 0.15 e Å3
3972 reflectionsAbsolute structure: Flack (1983), 436 Friedel pairs
383 parametersAbsolute structure parameter: 0.01 (7)
2 restraints
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
S10.04136 (4)0.91899 (12)0.39817 (5)0.0679 (2)
S20.11933 (4)0.72625 (12)0.20956 (5)0.0718 (3)
O10.07728 (10)0.7514 (4)0.73258 (15)0.0790 (7)
O20.23882 (10)0.7938 (3)0.61883 (15)0.0718 (6)
O30.18794 (12)0.8394 (4)0.48764 (17)0.0861 (7)
O40.03343 (9)0.5761 (4)0.14800 (12)0.0723 (7)
O50.22943 (10)0.6905 (4)0.16330 (14)0.0796 (7)
O60.20959 (9)0.6529 (3)0.03736 (13)0.0690 (6)
N10.02812 (10)0.8631 (3)0.53063 (14)0.0518 (6)
N20.06663 (10)0.8286 (3)0.61146 (14)0.0504 (6)
N30.02469 (10)0.6134 (3)0.01498 (13)0.0474 (6)
N40.02837 (12)0.6482 (4)0.06007 (14)0.0528 (6)
C10.05586 (14)0.9944 (5)0.5884 (2)0.0630 (8)
H10.03761.05360.56090.076*
C20.11539 (15)1.0425 (5)0.5753 (2)0.0786 (10)
H20.13671.13590.53990.094*
C30.14311 (15)0.9528 (6)0.6142 (2)0.0810 (11)
H30.18320.98530.60530.097*
C40.11182 (17)0.8156 (6)0.6662 (2)0.0775 (11)
H40.13120.75290.69150.093*
C50.05203 (15)0.7694 (5)0.6815 (2)0.0652 (9)
H50.03060.67820.71820.078*
C60.02351 (14)0.8587 (4)0.64222 (19)0.0532 (7)
C70.04247 (13)0.8082 (4)0.66675 (19)0.0542 (7)
C80.12818 (12)0.8182 (4)0.62826 (18)0.0479 (7)
C90.18531 (13)0.7763 (4)0.70407 (19)0.0572 (8)
H9A0.18760.64740.71460.069*
H9B0.18400.83900.74850.069*
C100.24181 (13)0.8363 (5)0.6959 (2)0.0658 (8)
H100.24560.96780.70300.079*
C110.30170 (15)0.7518 (6)0.7584 (3)0.0881 (12)
H11A0.29900.62270.75240.132*
H11B0.30770.78350.81090.132*
H11C0.33650.79550.75150.132*
C120.18652 (15)0.8317 (5)0.5508 (2)0.0617 (8)
C130.12973 (13)0.8487 (4)0.55818 (18)0.0475 (7)
C140.06669 (13)0.8751 (4)0.49927 (17)0.0490 (7)
C150.04159 (17)0.9176 (6)0.3615 (2)0.0873 (12)
H15A0.05490.79840.36720.131*
H15B0.06210.95170.30590.131*
H15C0.05251.00190.39180.131*
C160.14289 (13)0.6791 (5)0.13527 (18)0.0588 (8)
H160.13830.74230.17490.071*
C170.20015 (14)0.6773 (5)0.1355 (2)0.0689 (9)
H170.23390.74140.17430.083*
C180.20692 (15)0.5801 (5)0.0779 (2)0.0750 (10)
H180.24540.57810.07770.090*
C190.15721 (17)0.4863 (6)0.0208 (2)0.0805 (11)
H190.16240.41850.01720.097*
C200.09922 (14)0.4913 (5)0.01922 (19)0.0649 (9)
H200.06520.42990.02050.078*
C210.09244 (13)0.5880 (4)0.07685 (18)0.0506 (7)
C220.03339 (13)0.5895 (4)0.08434 (18)0.0512 (7)
C230.08835 (14)0.6767 (4)0.10783 (17)0.0503 (7)
C240.0529 (2)0.6934 (6)0.2263 (2)0.0889 (12)
H24A0.01810.76250.18780.133*
H24B0.06290.73270.27950.133*
H24C0.04190.56750.22050.133*
C250.12368 (13)0.6642 (4)0.06572 (17)0.0478 (7)
C260.19096 (14)0.6730 (4)0.09394 (19)0.0565 (7)
C270.16678 (14)0.6694 (6)0.0464 (2)0.0692 (9)
H270.16080.79950.05730.083*
C280.19932 (15)0.6019 (6)0.0921 (2)0.0752 (10)
H28A0.23800.66670.07540.113*
H28B0.17290.62050.14850.113*
H28C0.20800.47520.08180.113*
C290.10223 (13)0.5921 (4)0.07399 (18)0.0527 (7)
H29A0.07280.64930.12380.063*
H29B0.10260.46330.08360.063*
C300.08257 (12)0.6238 (4)0.01167 (16)0.0432 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0748 (5)0.0783 (6)0.0466 (5)0.0030 (5)0.0250 (4)0.0028 (4)
S20.0845 (6)0.0811 (6)0.0398 (4)0.0050 (5)0.0204 (4)0.0053 (4)
O10.0592 (13)0.118 (2)0.0595 (16)0.0151 (13)0.0271 (12)0.0298 (14)
O20.0488 (12)0.0933 (18)0.0761 (17)0.0066 (11)0.0316 (12)0.0051 (13)
O30.0764 (16)0.119 (2)0.0804 (19)0.0025 (15)0.0507 (15)0.0036 (16)
O40.0501 (12)0.122 (2)0.0393 (12)0.0099 (12)0.0165 (10)0.0082 (12)
O50.0519 (13)0.113 (2)0.0510 (14)0.0005 (12)0.0052 (12)0.0143 (13)
O60.0452 (11)0.1025 (18)0.0505 (13)0.0034 (11)0.0150 (11)0.0045 (12)
N10.0446 (13)0.0598 (16)0.0452 (15)0.0024 (11)0.0161 (12)0.0027 (12)
N20.0419 (13)0.0593 (16)0.0467 (15)0.0007 (10)0.0179 (12)0.0014 (12)
N30.0450 (13)0.0563 (15)0.0374 (13)0.0014 (11)0.0164 (11)0.0023 (11)
N40.0578 (15)0.0607 (16)0.0402 (14)0.0044 (12)0.0232 (13)0.0001 (11)
C10.0508 (17)0.069 (2)0.069 (2)0.0023 (15)0.0271 (16)0.0052 (17)
C20.0540 (18)0.090 (3)0.084 (3)0.0114 (18)0.0258 (18)0.004 (2)
C30.0441 (17)0.122 (3)0.072 (3)0.008 (2)0.0237 (18)0.027 (2)
C40.064 (2)0.118 (3)0.064 (2)0.018 (2)0.041 (2)0.014 (2)
C50.064 (2)0.089 (3)0.0493 (19)0.0066 (17)0.0320 (16)0.0008 (17)
C60.0496 (16)0.0627 (19)0.0484 (17)0.0056 (14)0.0236 (14)0.0077 (15)
C70.0470 (16)0.064 (2)0.0489 (19)0.0033 (14)0.0204 (15)0.0002 (15)
C80.0421 (15)0.0478 (17)0.0504 (18)0.0004 (12)0.0188 (13)0.0026 (13)
C90.0491 (17)0.061 (2)0.054 (2)0.0039 (14)0.0180 (15)0.0011 (15)
C100.0473 (17)0.073 (2)0.068 (2)0.0006 (15)0.0191 (16)0.0064 (18)
C110.0436 (17)0.108 (3)0.089 (3)0.0104 (18)0.0106 (18)0.006 (2)
C120.0565 (19)0.064 (2)0.069 (2)0.0011 (15)0.0331 (18)0.0004 (17)
C130.0477 (16)0.0438 (17)0.0498 (18)0.0036 (12)0.0215 (14)0.0033 (13)
C140.0520 (17)0.0440 (16)0.0494 (18)0.0039 (13)0.0223 (15)0.0077 (13)
C150.070 (2)0.097 (3)0.059 (2)0.003 (2)0.0004 (18)0.015 (2)
C160.0498 (17)0.076 (2)0.0446 (17)0.0020 (15)0.0171 (14)0.0059 (16)
C170.0486 (17)0.084 (2)0.063 (2)0.0046 (16)0.0171 (16)0.0000 (18)
C180.0542 (19)0.100 (3)0.074 (2)0.0128 (18)0.0323 (18)0.014 (2)
C190.071 (2)0.111 (3)0.064 (2)0.015 (2)0.036 (2)0.013 (2)
C200.0573 (18)0.076 (2)0.055 (2)0.0027 (16)0.0202 (16)0.0159 (17)
C210.0453 (15)0.0594 (19)0.0410 (16)0.0041 (13)0.0149 (13)0.0000 (14)
C220.0481 (16)0.059 (2)0.0418 (17)0.0003 (13)0.0174 (14)0.0031 (13)
C230.0566 (18)0.0455 (17)0.0402 (16)0.0050 (14)0.0154 (14)0.0006 (13)
C240.122 (3)0.098 (3)0.059 (2)0.030 (2)0.053 (2)0.015 (2)
C250.0498 (16)0.0453 (16)0.0410 (17)0.0046 (12)0.0150 (13)0.0017 (12)
C260.0506 (17)0.0559 (19)0.0473 (18)0.0024 (13)0.0098 (15)0.0034 (14)
C270.0494 (19)0.099 (3)0.051 (2)0.0013 (17)0.0168 (15)0.0055 (18)
C280.0538 (19)0.113 (3)0.061 (2)0.0045 (18)0.0285 (17)0.005 (2)
C290.0499 (17)0.061 (2)0.0447 (18)0.0000 (14)0.0199 (14)0.0024 (14)
C300.0437 (15)0.0422 (16)0.0403 (16)0.0027 (11)0.0167 (13)0.0018 (12)
Geometric parameters (Å, º) top
S1—C141.737 (3)C10—C111.508 (5)
S1—C151.784 (4)C10—H100.9800
S2—C231.739 (3)C11—H11A0.9600
S2—C241.786 (4)C11—H11B0.9600
O1—C71.202 (4)C11—H11C0.9600
O2—C121.343 (4)C12—C131.443 (4)
O2—C101.452 (4)C13—C141.416 (4)
O3—C121.206 (4)C15—H15A0.9600
O4—C221.202 (3)C15—H15B0.9600
O5—C261.205 (4)C15—H15C0.9600
O6—C261.343 (4)C16—C211.376 (4)
O6—C271.432 (4)C16—C171.377 (4)
N1—C141.315 (4)C16—H160.9300
N1—N21.387 (3)C17—C181.372 (5)
N2—C81.366 (3)C17—H170.9300
N2—C71.417 (4)C18—C191.368 (5)
N3—C301.368 (3)C18—H180.9300
N3—N41.397 (3)C19—C201.383 (4)
N3—C221.411 (3)C19—H190.9300
N4—C231.315 (4)C20—C211.371 (4)
C1—C61.380 (4)C20—H200.9300
C1—C21.383 (4)C21—C221.493 (4)
C1—H10.9300C23—C251.410 (4)
C2—C31.370 (5)C24—H24A0.9600
C2—H20.9300C24—H24B0.9600
C3—C41.367 (6)C24—H24C0.9600
C3—H30.9300C25—C301.359 (4)
C4—C51.374 (5)C25—C261.453 (4)
C4—H40.9300C27—C281.493 (5)
C5—C61.389 (4)C27—C291.504 (4)
C5—H50.9300C27—H270.9800
C6—C71.481 (4)C28—H28A0.9600
C8—C131.356 (4)C28—H28B0.9600
C8—C91.482 (4)C28—H28C0.9600
C9—C101.506 (4)C29—C301.474 (4)
C9—H9A0.9700C29—H29A0.9700
C9—H9B0.9700C29—H29B0.9700
C14—S1—C15100.41 (17)S1—C15—H15A109.5
C23—S2—C24101.85 (17)S1—C15—H15B109.5
C12—O2—C10119.7 (2)H15A—C15—H15B109.5
C26—O6—C27121.9 (2)S1—C15—H15C109.5
C14—N1—N2104.7 (2)H15A—C15—H15C109.5
C8—N2—N1111.3 (2)H15B—C15—H15C109.5
C8—N2—C7126.6 (2)C21—C16—C17120.5 (3)
N1—N2—C7122.1 (2)C21—C16—H16119.7
C30—N3—N4111.1 (2)C17—C16—H16119.7
C30—N3—C22126.8 (2)C18—C17—C16119.3 (3)
N4—N3—C22121.8 (2)C18—C17—H17120.3
C23—N4—N3104.6 (2)C16—C17—H17120.3
C6—C1—C2120.1 (3)C19—C18—C17120.2 (3)
C6—C1—H1119.9C19—C18—H18119.9
C2—C1—H1119.9C17—C18—H18119.9
C3—C2—C1120.2 (4)C18—C19—C20120.6 (3)
C3—C2—H2119.9C18—C19—H19119.7
C1—C2—H2119.9C20—C19—H19119.7
C4—C3—C2119.9 (3)C21—C20—C19119.2 (3)
C4—C3—H3120.0C21—C20—H20120.4
C2—C3—H3120.0C19—C20—H20120.4
C3—C4—C5120.6 (3)C20—C21—C16120.1 (3)
C3—C4—H4119.7C20—C21—C22123.2 (3)
C5—C4—H4119.7C16—C21—C22116.5 (3)
C4—C5—C6120.0 (3)O4—C22—N3118.2 (3)
C4—C5—H5120.0O4—C22—C21122.4 (3)
C6—C5—H5120.0N3—C22—C21119.4 (3)
C1—C6—C5119.1 (3)N4—C23—C25111.3 (2)
C1—C6—C7124.7 (3)N4—C23—S2123.9 (2)
C5—C6—C7116.0 (3)C25—C23—S2124.8 (2)
O1—C7—N2117.8 (3)S2—C24—H24A109.5
O1—C7—C6122.8 (3)S2—C24—H24B109.5
N2—C7—C6119.5 (3)H24A—C24—H24B109.5
C13—C8—N2106.5 (3)S2—C24—H24C109.5
C13—C8—C9122.5 (2)H24A—C24—H24C109.5
N2—C8—C9130.9 (3)H24B—C24—H24C109.5
C8—C9—C10108.5 (3)C30—C25—C23106.7 (2)
C8—C9—H9A110.0C30—C25—C26122.2 (3)
C10—C9—H9A110.0C23—C25—C26130.8 (3)
C8—C9—H9B110.0O5—C26—O6119.9 (3)
C10—C9—H9B110.0O5—C26—C25124.4 (3)
H9A—C9—H9B108.4O6—C26—C25115.7 (3)
O2—C10—C9114.3 (3)O6—C27—C28107.7 (3)
O2—C10—C11105.9 (3)O6—C27—C29116.5 (3)
C9—C10—C11112.3 (3)C28—C27—C29114.2 (3)
O2—C10—H10108.0O6—C27—H27105.9
C9—C10—H10108.0C28—C27—H27105.9
C11—C10—H10108.0C29—C27—H27105.9
C10—C11—H11A109.5C27—C28—H28A109.5
C10—C11—H11B109.5C27—C28—H28B109.5
H11A—C11—H11B109.5H28A—C28—H28B109.5
C10—C11—H11C109.5C27—C28—H28C109.5
H11A—C11—H11C109.5H28A—C28—H28C109.5
H11B—C11—H11C109.5H28B—C28—H28C109.5
O3—C12—O2120.3 (3)C30—C29—C27109.2 (3)
O3—C12—C13123.6 (3)C30—C29—H29A109.8
O2—C12—C13115.9 (3)C27—C29—H29A109.8
C8—C13—C14106.2 (2)C30—C29—H29B109.8
C8—C13—C12122.4 (3)C27—C29—H29B109.8
C14—C13—C12130.9 (3)H29A—C29—H29B108.3
N1—C14—C13111.3 (3)C25—C30—N3106.2 (2)
N1—C14—S1122.9 (2)C25—C30—C29123.0 (2)
C13—C14—S1125.8 (2)N3—C30—C29130.8 (3)
C14—N1—N2—C80.6 (3)C15—S1—C14—N14.7 (3)
C14—N1—N2—C7179.4 (3)C15—S1—C14—C13175.6 (3)
C30—N3—N4—C230.8 (3)C21—C16—C17—C181.6 (5)
C22—N3—N4—C23175.1 (3)C16—C17—C18—C190.1 (6)
C6—C1—C2—C31.5 (5)C17—C18—C19—C201.5 (6)
C1—C2—C3—C40.1 (6)C18—C19—C20—C211.6 (6)
C2—C3—C4—C51.7 (6)C19—C20—C21—C160.2 (5)
C3—C4—C5—C61.9 (6)C19—C20—C21—C22174.8 (3)
C2—C1—C6—C51.3 (5)C17—C16—C21—C201.4 (5)
C2—C1—C6—C7173.8 (3)C17—C16—C21—C22176.7 (3)
C4—C5—C6—C10.4 (5)C30—N3—C22—O40.1 (4)
C4—C5—C6—C7176.0 (3)N4—N3—C22—O4173.5 (3)
C8—N2—C7—O111.2 (5)C30—N3—C22—C21177.7 (3)
N1—N2—C7—O1168.8 (3)N4—N3—C22—C214.4 (4)
C8—N2—C7—C6168.0 (3)C20—C21—C22—O4135.9 (4)
N1—N2—C7—C612.0 (4)C16—C21—C22—O439.2 (4)
C1—C6—C7—O1148.0 (4)C20—C21—C22—N346.3 (4)
C5—C6—C7—O127.3 (5)C16—C21—C22—N3138.6 (3)
C1—C6—C7—N231.3 (4)N3—N4—C23—C250.9 (3)
C5—C6—C7—N2153.5 (3)N3—N4—C23—S2179.9 (2)
N1—N2—C8—C130.9 (3)C24—S2—C23—N47.7 (3)
C7—N2—C8—C13179.1 (3)C24—S2—C23—C25173.1 (3)
N1—N2—C8—C9176.9 (3)N4—C23—C25—C300.7 (3)
C7—N2—C8—C93.1 (5)S2—C23—C25—C30179.9 (2)
C13—C8—C9—C1019.2 (4)N4—C23—C25—C26175.2 (3)
N2—C8—C9—C10163.4 (3)S2—C23—C25—C265.5 (5)
C12—O2—C10—C947.4 (4)C27—O6—C26—O5166.7 (3)
C12—O2—C10—C11171.6 (3)C27—O6—C26—C2515.8 (4)
C8—C9—C10—O242.3 (4)C30—C25—C26—O5172.3 (3)
C8—C9—C10—C11163.0 (3)C23—C25—C26—O51.5 (5)
C10—O2—C12—O3161.9 (3)C30—C25—C26—O65.1 (4)
C10—O2—C12—C1322.4 (4)C23—C25—C26—O6178.9 (3)
N2—C8—C13—C140.8 (3)C26—O6—C27—C28168.3 (3)
C9—C8—C13—C14177.2 (3)C26—O6—C27—C2938.6 (5)
N2—C8—C13—C12174.1 (3)O6—C27—C29—C3036.9 (4)
C9—C8—C13—C123.9 (4)C28—C27—C29—C30163.5 (3)
O3—C12—C13—C8171.9 (3)C23—C25—C30—N30.1 (3)
O2—C12—C13—C83.7 (4)C26—C25—C30—N3175.3 (3)
O3—C12—C13—C140.4 (6)C23—C25—C30—C29177.4 (3)
O2—C12—C13—C14175.1 (3)C26—C25—C30—C292.2 (5)
N2—N1—C14—C130.1 (3)N4—N3—C30—C250.4 (3)
N2—N1—C14—S1179.6 (2)C22—N3—C30—C25174.3 (3)
C8—C13—C14—N10.4 (3)N4—N3—C30—C29177.6 (3)
C12—C13—C14—N1172.9 (3)C22—N3—C30—C298.4 (5)
C8—C13—C14—S1179.9 (2)C27—C29—C30—C2518.4 (4)
C12—C13—C14—S17.4 (5)C27—C29—C30—N3164.7 (3)

Experimental details

Crystal data
Chemical formulaC15H14N2O3S
Mr302.35
Crystal system, space groupMonoclinic, Cc
Temperature (K)293
a, b, c (Å)24.083 (3), 7.393 (1), 18.820 (3)
β (°) 117.765 (2)
V3)2965.2 (7)
Z8
Radiation typeMo Kα
µ (mm1)0.23
Crystal size (mm)0.38 × 0.20 × 0.10
Data collection
DiffractometerBruker APEX-II CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.725, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
7700, 3972, 3298
Rint0.020
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.083, 1.04
No. of reflections3972
No. of parameters383
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.15
Absolute structureFlack (1983), 436 Friedel pairs
Absolute structure parameter0.01 (7)

Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.

 

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