Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025547/ww6380sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025547/ww6380Isup2.hkl |
CCDC reference: 287752
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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%.
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).
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.
C15H14N2O3S | F(000) = 1264 |
Mr = 302.35 | Dx = 1.354 Mg m−3 |
Monoclinic, Cc | Melting point: 409 K |
Hall symbol: C -2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 24.083 (3) Å | Cell parameters from 2146 reflections |
b = 7.393 (1) Å | θ = 2.3–23.6° |
c = 18.820 (3) Å | µ = 0.23 mm−1 |
β = 117.765 (2)° | T = 293 K |
V = 2965.2 (7) Å3 | Block, colourless |
Z = 8 | 0.38 × 0.20 × 0.10 mm |
Bruker APEX-II CCD area-detector diffractometer | 3972 independent reflections |
Radiation source: fine-focus sealed tube | 3298 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −28→28 |
Tmin = 0.725, Tmax = 1.000 | k = −8→8 |
7700 measured reflections | l = −22→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-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 reflections | Δρmax = 0.16 e Å−3 |
383 parameters | Δρmin = −0.15 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 436 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.01 (7) |
C15H14N2O3S | V = 2965.2 (7) Å3 |
Mr = 302.35 | Z = 8 |
Monoclinic, Cc | Mo Kα radiation |
a = 24.083 (3) Å | µ = 0.23 mm−1 |
b = 7.393 (1) Å | T = 293 K |
c = 18.820 (3) Å | 0.38 × 0.20 × 0.10 mm |
β = 117.765 (2)° |
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 = 1.000 | Rint = 0.020 |
7700 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.083 | Δρmax = 0.16 e Å−3 |
S = 1.04 | Δρmin = −0.15 e Å−3 |
3972 reflections | Absolute structure: Flack (1983), 436 Friedel pairs |
383 parameters | Absolute structure parameter: −0.01 (7) |
2 restraints |
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 | 0.04136 (4) | 0.91899 (12) | 0.39817 (5) | 0.0679 (2) | |
S2 | 0.11933 (4) | 0.72625 (12) | 0.20956 (5) | 0.0718 (3) | |
O1 | 0.07728 (10) | 0.7514 (4) | 0.73258 (15) | 0.0790 (7) | |
O2 | 0.23882 (10) | 0.7938 (3) | 0.61883 (15) | 0.0718 (6) | |
O3 | 0.18794 (12) | 0.8394 (4) | 0.48764 (17) | 0.0861 (7) | |
O4 | −0.03343 (9) | 0.5761 (4) | −0.14800 (12) | 0.0723 (7) | |
O5 | 0.22943 (10) | 0.6905 (4) | 0.16330 (14) | 0.0796 (7) | |
O6 | 0.20959 (9) | 0.6529 (3) | 0.03736 (13) | 0.0690 (6) | |
N1 | 0.02812 (10) | 0.8631 (3) | 0.53063 (14) | 0.0518 (6) | |
N2 | 0.06663 (10) | 0.8286 (3) | 0.61146 (14) | 0.0504 (6) | |
N3 | 0.02469 (10) | 0.6134 (3) | −0.01498 (13) | 0.0474 (6) | |
N4 | 0.02837 (12) | 0.6482 (4) | 0.06007 (14) | 0.0528 (6) | |
C1 | −0.05586 (14) | 0.9944 (5) | 0.5884 (2) | 0.0630 (8) | |
H1 | −0.0376 | 1.0536 | 0.5609 | 0.076* | |
C2 | −0.11539 (15) | 1.0425 (5) | 0.5753 (2) | 0.0786 (10) | |
H2 | −0.1367 | 1.1359 | 0.5399 | 0.094* | |
C3 | −0.14311 (15) | 0.9528 (6) | 0.6142 (2) | 0.0810 (11) | |
H3 | −0.1832 | 0.9853 | 0.6053 | 0.097* | |
C4 | −0.11182 (17) | 0.8156 (6) | 0.6662 (2) | 0.0775 (11) | |
H4 | −0.1312 | 0.7529 | 0.6915 | 0.093* | |
C5 | −0.05203 (15) | 0.7694 (5) | 0.6815 (2) | 0.0652 (9) | |
H5 | −0.0306 | 0.6782 | 0.7182 | 0.078* | |
C6 | −0.02351 (14) | 0.8587 (4) | 0.64222 (19) | 0.0532 (7) | |
C7 | 0.04247 (13) | 0.8082 (4) | 0.66675 (19) | 0.0542 (7) | |
C8 | 0.12818 (12) | 0.8182 (4) | 0.62826 (18) | 0.0479 (7) | |
C9 | 0.18531 (13) | 0.7763 (4) | 0.70407 (19) | 0.0572 (8) | |
H9A | 0.1876 | 0.6474 | 0.7146 | 0.069* | |
H9B | 0.1840 | 0.8390 | 0.7485 | 0.069* | |
C10 | 0.24181 (13) | 0.8363 (5) | 0.6959 (2) | 0.0658 (8) | |
H10 | 0.2456 | 0.9678 | 0.7030 | 0.079* | |
C11 | 0.30170 (15) | 0.7518 (6) | 0.7584 (3) | 0.0881 (12) | |
H11A | 0.2990 | 0.6227 | 0.7524 | 0.132* | |
H11B | 0.3077 | 0.7835 | 0.8109 | 0.132* | |
H11C | 0.3365 | 0.7955 | 0.7515 | 0.132* | |
C12 | 0.18652 (15) | 0.8317 (5) | 0.5508 (2) | 0.0617 (8) | |
C13 | 0.12973 (13) | 0.8487 (4) | 0.55818 (18) | 0.0475 (7) | |
C14 | 0.06669 (13) | 0.8751 (4) | 0.49927 (17) | 0.0490 (7) | |
C15 | −0.04159 (17) | 0.9176 (6) | 0.3615 (2) | 0.0873 (12) | |
H15A | −0.0549 | 0.7984 | 0.3672 | 0.131* | |
H15B | −0.0621 | 0.9517 | 0.3059 | 0.131* | |
H15C | −0.0525 | 1.0019 | 0.3918 | 0.131* | |
C16 | −0.14289 (13) | 0.6791 (5) | −0.13527 (18) | 0.0588 (8) | |
H16 | −0.1383 | 0.7423 | −0.1749 | 0.071* | |
C17 | −0.20015 (14) | 0.6773 (5) | −0.1355 (2) | 0.0689 (9) | |
H17 | −0.2339 | 0.7414 | −0.1743 | 0.083* | |
C18 | −0.20692 (15) | 0.5801 (5) | −0.0779 (2) | 0.0750 (10) | |
H18 | −0.2454 | 0.5781 | −0.0777 | 0.090* | |
C19 | −0.15721 (17) | 0.4863 (6) | −0.0208 (2) | 0.0805 (11) | |
H19 | −0.1624 | 0.4185 | 0.0172 | 0.097* | |
C20 | −0.09922 (14) | 0.4913 (5) | −0.01922 (19) | 0.0649 (9) | |
H20 | −0.0652 | 0.4299 | 0.0205 | 0.078* | |
C21 | −0.09244 (13) | 0.5880 (4) | −0.07685 (18) | 0.0506 (7) | |
C22 | −0.03339 (13) | 0.5895 (4) | −0.08434 (18) | 0.0512 (7) | |
C23 | 0.08835 (14) | 0.6767 (4) | 0.10783 (17) | 0.0503 (7) | |
C24 | 0.0529 (2) | 0.6934 (6) | 0.2263 (2) | 0.0889 (12) | |
H24A | 0.0181 | 0.7625 | 0.1878 | 0.133* | |
H24B | 0.0629 | 0.7327 | 0.2795 | 0.133* | |
H24C | 0.0419 | 0.5675 | 0.2205 | 0.133* | |
C25 | 0.12368 (13) | 0.6642 (4) | 0.06572 (17) | 0.0478 (7) | |
C26 | 0.19096 (14) | 0.6730 (4) | 0.09394 (19) | 0.0565 (7) | |
C27 | 0.16678 (14) | 0.6694 (6) | −0.0464 (2) | 0.0692 (9) | |
H27 | 0.1608 | 0.7995 | −0.0573 | 0.083* | |
C28 | 0.19932 (15) | 0.6019 (6) | −0.0921 (2) | 0.0752 (10) | |
H28A | 0.2380 | 0.6667 | −0.0754 | 0.113* | |
H28B | 0.1729 | 0.6205 | −0.1485 | 0.113* | |
H28C | 0.2080 | 0.4752 | −0.0818 | 0.113* | |
C29 | 0.10223 (13) | 0.5921 (4) | −0.07399 (18) | 0.0527 (7) | |
H29A | 0.0728 | 0.6493 | −0.1238 | 0.063* | |
H29B | 0.1026 | 0.4633 | −0.0836 | 0.063* | |
C30 | 0.08257 (12) | 0.6238 (4) | −0.01167 (16) | 0.0432 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0748 (5) | 0.0783 (6) | 0.0466 (5) | −0.0030 (5) | 0.0250 (4) | −0.0028 (4) |
S2 | 0.0845 (6) | 0.0811 (6) | 0.0398 (4) | 0.0050 (5) | 0.0204 (4) | −0.0053 (4) |
O1 | 0.0592 (13) | 0.118 (2) | 0.0595 (16) | 0.0151 (13) | 0.0271 (12) | 0.0298 (14) |
O2 | 0.0488 (12) | 0.0933 (18) | 0.0761 (17) | 0.0066 (11) | 0.0316 (12) | −0.0051 (13) |
O3 | 0.0764 (16) | 0.119 (2) | 0.0804 (19) | 0.0025 (15) | 0.0507 (15) | 0.0036 (16) |
O4 | 0.0501 (12) | 0.122 (2) | 0.0393 (12) | −0.0099 (12) | 0.0165 (10) | −0.0082 (12) |
O5 | 0.0519 (13) | 0.113 (2) | 0.0510 (14) | −0.0005 (12) | 0.0052 (12) | −0.0143 (13) |
O6 | 0.0452 (11) | 0.1025 (18) | 0.0505 (13) | 0.0034 (11) | 0.0150 (11) | −0.0045 (12) |
N1 | 0.0446 (13) | 0.0598 (16) | 0.0452 (15) | −0.0024 (11) | 0.0161 (12) | −0.0027 (12) |
N2 | 0.0419 (13) | 0.0593 (16) | 0.0467 (15) | −0.0007 (10) | 0.0179 (12) | 0.0014 (12) |
N3 | 0.0450 (13) | 0.0563 (15) | 0.0374 (13) | 0.0014 (11) | 0.0164 (11) | −0.0023 (11) |
N4 | 0.0578 (15) | 0.0607 (16) | 0.0402 (14) | 0.0044 (12) | 0.0232 (13) | −0.0001 (11) |
C1 | 0.0508 (17) | 0.069 (2) | 0.069 (2) | 0.0023 (15) | 0.0271 (16) | 0.0052 (17) |
C2 | 0.0540 (18) | 0.090 (3) | 0.084 (3) | 0.0114 (18) | 0.0258 (18) | 0.004 (2) |
C3 | 0.0441 (17) | 0.122 (3) | 0.072 (3) | −0.008 (2) | 0.0237 (18) | −0.027 (2) |
C4 | 0.064 (2) | 0.118 (3) | 0.064 (2) | −0.018 (2) | 0.041 (2) | −0.014 (2) |
C5 | 0.064 (2) | 0.089 (3) | 0.0493 (19) | −0.0066 (17) | 0.0320 (16) | −0.0008 (17) |
C6 | 0.0496 (16) | 0.0627 (19) | 0.0484 (17) | −0.0056 (14) | 0.0236 (14) | −0.0077 (15) |
C7 | 0.0470 (16) | 0.064 (2) | 0.0489 (19) | −0.0033 (14) | 0.0204 (15) | −0.0002 (15) |
C8 | 0.0421 (15) | 0.0478 (17) | 0.0504 (18) | 0.0004 (12) | 0.0188 (13) | −0.0026 (13) |
C9 | 0.0491 (17) | 0.061 (2) | 0.054 (2) | 0.0039 (14) | 0.0180 (15) | −0.0011 (15) |
C10 | 0.0473 (17) | 0.073 (2) | 0.068 (2) | 0.0006 (15) | 0.0191 (16) | −0.0064 (18) |
C11 | 0.0436 (17) | 0.108 (3) | 0.089 (3) | 0.0104 (18) | 0.0106 (18) | −0.006 (2) |
C12 | 0.0565 (19) | 0.064 (2) | 0.069 (2) | 0.0011 (15) | 0.0331 (18) | −0.0004 (17) |
C13 | 0.0477 (16) | 0.0438 (17) | 0.0498 (18) | −0.0036 (12) | 0.0215 (14) | −0.0033 (13) |
C14 | 0.0520 (17) | 0.0440 (16) | 0.0494 (18) | −0.0039 (13) | 0.0223 (15) | −0.0077 (13) |
C15 | 0.070 (2) | 0.097 (3) | 0.059 (2) | 0.003 (2) | 0.0004 (18) | 0.015 (2) |
C16 | 0.0498 (17) | 0.076 (2) | 0.0446 (17) | −0.0020 (15) | 0.0171 (14) | 0.0059 (16) |
C17 | 0.0486 (17) | 0.084 (2) | 0.063 (2) | 0.0046 (16) | 0.0171 (16) | 0.0000 (18) |
C18 | 0.0542 (19) | 0.100 (3) | 0.074 (2) | −0.0128 (18) | 0.0323 (18) | −0.014 (2) |
C19 | 0.071 (2) | 0.111 (3) | 0.064 (2) | −0.015 (2) | 0.036 (2) | 0.013 (2) |
C20 | 0.0573 (18) | 0.076 (2) | 0.055 (2) | −0.0027 (16) | 0.0202 (16) | 0.0159 (17) |
C21 | 0.0453 (15) | 0.0594 (19) | 0.0410 (16) | −0.0041 (13) | 0.0149 (13) | 0.0000 (14) |
C22 | 0.0481 (16) | 0.059 (2) | 0.0418 (17) | −0.0003 (13) | 0.0174 (14) | 0.0031 (13) |
C23 | 0.0566 (18) | 0.0455 (17) | 0.0402 (16) | 0.0050 (14) | 0.0154 (14) | −0.0006 (13) |
C24 | 0.122 (3) | 0.098 (3) | 0.059 (2) | 0.030 (2) | 0.053 (2) | 0.015 (2) |
C25 | 0.0498 (16) | 0.0453 (16) | 0.0410 (17) | 0.0046 (12) | 0.0150 (13) | −0.0017 (12) |
C26 | 0.0506 (17) | 0.0559 (19) | 0.0473 (18) | 0.0024 (13) | 0.0098 (15) | −0.0034 (14) |
C27 | 0.0494 (19) | 0.099 (3) | 0.051 (2) | −0.0013 (17) | 0.0168 (15) | 0.0055 (18) |
C28 | 0.0538 (19) | 0.113 (3) | 0.061 (2) | 0.0045 (18) | 0.0285 (17) | 0.005 (2) |
C29 | 0.0499 (17) | 0.061 (2) | 0.0447 (18) | 0.0000 (14) | 0.0199 (14) | −0.0024 (14) |
C30 | 0.0437 (15) | 0.0422 (16) | 0.0403 (16) | 0.0027 (11) | 0.0167 (13) | 0.0018 (12) |
S1—C14 | 1.737 (3) | C10—C11 | 1.508 (5) |
S1—C15 | 1.784 (4) | C10—H10 | 0.9800 |
S2—C23 | 1.739 (3) | C11—H11A | 0.9600 |
S2—C24 | 1.786 (4) | C11—H11B | 0.9600 |
O1—C7 | 1.202 (4) | C11—H11C | 0.9600 |
O2—C12 | 1.343 (4) | C12—C13 | 1.443 (4) |
O2—C10 | 1.452 (4) | C13—C14 | 1.416 (4) |
O3—C12 | 1.206 (4) | C15—H15A | 0.9600 |
O4—C22 | 1.202 (3) | C15—H15B | 0.9600 |
O5—C26 | 1.205 (4) | C15—H15C | 0.9600 |
O6—C26 | 1.343 (4) | C16—C21 | 1.376 (4) |
O6—C27 | 1.432 (4) | C16—C17 | 1.377 (4) |
N1—C14 | 1.315 (4) | C16—H16 | 0.9300 |
N1—N2 | 1.387 (3) | C17—C18 | 1.372 (5) |
N2—C8 | 1.366 (3) | C17—H17 | 0.9300 |
N2—C7 | 1.417 (4) | C18—C19 | 1.368 (5) |
N3—C30 | 1.368 (3) | C18—H18 | 0.9300 |
N3—N4 | 1.397 (3) | C19—C20 | 1.383 (4) |
N3—C22 | 1.411 (3) | C19—H19 | 0.9300 |
N4—C23 | 1.315 (4) | C20—C21 | 1.371 (4) |
C1—C6 | 1.380 (4) | C20—H20 | 0.9300 |
C1—C2 | 1.383 (4) | C21—C22 | 1.493 (4) |
C1—H1 | 0.9300 | C23—C25 | 1.410 (4) |
C2—C3 | 1.370 (5) | C24—H24A | 0.9600 |
C2—H2 | 0.9300 | C24—H24B | 0.9600 |
C3—C4 | 1.367 (6) | C24—H24C | 0.9600 |
C3—H3 | 0.9300 | C25—C30 | 1.359 (4) |
C4—C5 | 1.374 (5) | C25—C26 | 1.453 (4) |
C4—H4 | 0.9300 | C27—C28 | 1.493 (5) |
C5—C6 | 1.389 (4) | C27—C29 | 1.504 (4) |
C5—H5 | 0.9300 | C27—H27 | 0.9800 |
C6—C7 | 1.481 (4) | C28—H28A | 0.9600 |
C8—C13 | 1.356 (4) | C28—H28B | 0.9600 |
C8—C9 | 1.482 (4) | C28—H28C | 0.9600 |
C9—C10 | 1.506 (4) | C29—C30 | 1.474 (4) |
C9—H9A | 0.9700 | C29—H29A | 0.9700 |
C9—H9B | 0.9700 | C29—H29B | 0.9700 |
C14—S1—C15 | 100.41 (17) | S1—C15—H15A | 109.5 |
C23—S2—C24 | 101.85 (17) | S1—C15—H15B | 109.5 |
C12—O2—C10 | 119.7 (2) | H15A—C15—H15B | 109.5 |
C26—O6—C27 | 121.9 (2) | S1—C15—H15C | 109.5 |
C14—N1—N2 | 104.7 (2) | H15A—C15—H15C | 109.5 |
C8—N2—N1 | 111.3 (2) | H15B—C15—H15C | 109.5 |
C8—N2—C7 | 126.6 (2) | C21—C16—C17 | 120.5 (3) |
N1—N2—C7 | 122.1 (2) | C21—C16—H16 | 119.7 |
C30—N3—N4 | 111.1 (2) | C17—C16—H16 | 119.7 |
C30—N3—C22 | 126.8 (2) | C18—C17—C16 | 119.3 (3) |
N4—N3—C22 | 121.8 (2) | C18—C17—H17 | 120.3 |
C23—N4—N3 | 104.6 (2) | C16—C17—H17 | 120.3 |
C6—C1—C2 | 120.1 (3) | C19—C18—C17 | 120.2 (3) |
C6—C1—H1 | 119.9 | C19—C18—H18 | 119.9 |
C2—C1—H1 | 119.9 | C17—C18—H18 | 119.9 |
C3—C2—C1 | 120.2 (4) | C18—C19—C20 | 120.6 (3) |
C3—C2—H2 | 119.9 | C18—C19—H19 | 119.7 |
C1—C2—H2 | 119.9 | C20—C19—H19 | 119.7 |
C4—C3—C2 | 119.9 (3) | C21—C20—C19 | 119.2 (3) |
C4—C3—H3 | 120.0 | C21—C20—H20 | 120.4 |
C2—C3—H3 | 120.0 | C19—C20—H20 | 120.4 |
C3—C4—C5 | 120.6 (3) | C20—C21—C16 | 120.1 (3) |
C3—C4—H4 | 119.7 | C20—C21—C22 | 123.2 (3) |
C5—C4—H4 | 119.7 | C16—C21—C22 | 116.5 (3) |
C4—C5—C6 | 120.0 (3) | O4—C22—N3 | 118.2 (3) |
C4—C5—H5 | 120.0 | O4—C22—C21 | 122.4 (3) |
C6—C5—H5 | 120.0 | N3—C22—C21 | 119.4 (3) |
C1—C6—C5 | 119.1 (3) | N4—C23—C25 | 111.3 (2) |
C1—C6—C7 | 124.7 (3) | N4—C23—S2 | 123.9 (2) |
C5—C6—C7 | 116.0 (3) | C25—C23—S2 | 124.8 (2) |
O1—C7—N2 | 117.8 (3) | S2—C24—H24A | 109.5 |
O1—C7—C6 | 122.8 (3) | S2—C24—H24B | 109.5 |
N2—C7—C6 | 119.5 (3) | H24A—C24—H24B | 109.5 |
C13—C8—N2 | 106.5 (3) | S2—C24—H24C | 109.5 |
C13—C8—C9 | 122.5 (2) | H24A—C24—H24C | 109.5 |
N2—C8—C9 | 130.9 (3) | H24B—C24—H24C | 109.5 |
C8—C9—C10 | 108.5 (3) | C30—C25—C23 | 106.7 (2) |
C8—C9—H9A | 110.0 | C30—C25—C26 | 122.2 (3) |
C10—C9—H9A | 110.0 | C23—C25—C26 | 130.8 (3) |
C8—C9—H9B | 110.0 | O5—C26—O6 | 119.9 (3) |
C10—C9—H9B | 110.0 | O5—C26—C25 | 124.4 (3) |
H9A—C9—H9B | 108.4 | O6—C26—C25 | 115.7 (3) |
O2—C10—C9 | 114.3 (3) | O6—C27—C28 | 107.7 (3) |
O2—C10—C11 | 105.9 (3) | O6—C27—C29 | 116.5 (3) |
C9—C10—C11 | 112.3 (3) | C28—C27—C29 | 114.2 (3) |
O2—C10—H10 | 108.0 | O6—C27—H27 | 105.9 |
C9—C10—H10 | 108.0 | C28—C27—H27 | 105.9 |
C11—C10—H10 | 108.0 | C29—C27—H27 | 105.9 |
C10—C11—H11A | 109.5 | C27—C28—H28A | 109.5 |
C10—C11—H11B | 109.5 | C27—C28—H28B | 109.5 |
H11A—C11—H11B | 109.5 | H28A—C28—H28B | 109.5 |
C10—C11—H11C | 109.5 | C27—C28—H28C | 109.5 |
H11A—C11—H11C | 109.5 | H28A—C28—H28C | 109.5 |
H11B—C11—H11C | 109.5 | H28B—C28—H28C | 109.5 |
O3—C12—O2 | 120.3 (3) | C30—C29—C27 | 109.2 (3) |
O3—C12—C13 | 123.6 (3) | C30—C29—H29A | 109.8 |
O2—C12—C13 | 115.9 (3) | C27—C29—H29A | 109.8 |
C8—C13—C14 | 106.2 (2) | C30—C29—H29B | 109.8 |
C8—C13—C12 | 122.4 (3) | C27—C29—H29B | 109.8 |
C14—C13—C12 | 130.9 (3) | H29A—C29—H29B | 108.3 |
N1—C14—C13 | 111.3 (3) | C25—C30—N3 | 106.2 (2) |
N1—C14—S1 | 122.9 (2) | C25—C30—C29 | 123.0 (2) |
C13—C14—S1 | 125.8 (2) | N3—C30—C29 | 130.8 (3) |
C14—N1—N2—C8 | −0.6 (3) | C15—S1—C14—N1 | −4.7 (3) |
C14—N1—N2—C7 | 179.4 (3) | C15—S1—C14—C13 | 175.6 (3) |
C30—N3—N4—C23 | −0.8 (3) | C21—C16—C17—C18 | −1.6 (5) |
C22—N3—N4—C23 | −175.1 (3) | C16—C17—C18—C19 | 0.1 (6) |
C6—C1—C2—C3 | −1.5 (5) | C17—C18—C19—C20 | 1.5 (6) |
C1—C2—C3—C4 | 0.1 (6) | C18—C19—C20—C21 | −1.6 (6) |
C2—C3—C4—C5 | 1.7 (6) | C19—C20—C21—C16 | 0.2 (5) |
C3—C4—C5—C6 | −1.9 (6) | C19—C20—C21—C22 | −174.8 (3) |
C2—C1—C6—C5 | 1.3 (5) | C17—C16—C21—C20 | 1.4 (5) |
C2—C1—C6—C7 | −173.8 (3) | C17—C16—C21—C22 | 176.7 (3) |
C4—C5—C6—C1 | 0.4 (5) | C30—N3—C22—O4 | 0.1 (4) |
C4—C5—C6—C7 | 176.0 (3) | N4—N3—C22—O4 | 173.5 (3) |
C8—N2—C7—O1 | −11.2 (5) | C30—N3—C22—C21 | −177.7 (3) |
N1—N2—C7—O1 | 168.8 (3) | N4—N3—C22—C21 | −4.4 (4) |
C8—N2—C7—C6 | 168.0 (3) | C20—C21—C22—O4 | 135.9 (4) |
N1—N2—C7—C6 | −12.0 (4) | C16—C21—C22—O4 | −39.2 (4) |
C1—C6—C7—O1 | 148.0 (4) | C20—C21—C22—N3 | −46.3 (4) |
C5—C6—C7—O1 | −27.3 (5) | C16—C21—C22—N3 | 138.6 (3) |
C1—C6—C7—N2 | −31.3 (4) | N3—N4—C23—C25 | 0.9 (3) |
C5—C6—C7—N2 | 153.5 (3) | N3—N4—C23—S2 | −179.9 (2) |
N1—N2—C8—C13 | 0.9 (3) | C24—S2—C23—N4 | 7.7 (3) |
C7—N2—C8—C13 | −179.1 (3) | C24—S2—C23—C25 | −173.1 (3) |
N1—N2—C8—C9 | −176.9 (3) | N4—C23—C25—C30 | −0.7 (3) |
C7—N2—C8—C9 | 3.1 (5) | S2—C23—C25—C30 | −179.9 (2) |
C13—C8—C9—C10 | 19.2 (4) | N4—C23—C25—C26 | −175.2 (3) |
N2—C8—C9—C10 | −163.4 (3) | S2—C23—C25—C26 | 5.5 (5) |
C12—O2—C10—C9 | 47.4 (4) | C27—O6—C26—O5 | −166.7 (3) |
C12—O2—C10—C11 | 171.6 (3) | C27—O6—C26—C25 | 15.8 (4) |
C8—C9—C10—O2 | −42.3 (4) | C30—C25—C26—O5 | −172.3 (3) |
C8—C9—C10—C11 | −163.0 (3) | C23—C25—C26—O5 | 1.5 (5) |
C10—O2—C12—O3 | 161.9 (3) | C30—C25—C26—O6 | 5.1 (4) |
C10—O2—C12—C13 | −22.4 (4) | C23—C25—C26—O6 | 178.9 (3) |
N2—C8—C13—C14 | −0.8 (3) | C26—O6—C27—C28 | −168.3 (3) |
C9—C8—C13—C14 | 177.2 (3) | C26—O6—C27—C29 | −38.6 (5) |
N2—C8—C13—C12 | −174.1 (3) | O6—C27—C29—C30 | 36.9 (4) |
C9—C8—C13—C12 | 3.9 (4) | C28—C27—C29—C30 | 163.5 (3) |
O3—C12—C13—C8 | 171.9 (3) | C23—C25—C30—N3 | 0.1 (3) |
O2—C12—C13—C8 | −3.7 (4) | C26—C25—C30—N3 | 175.3 (3) |
O3—C12—C13—C14 | 0.4 (6) | C23—C25—C30—C29 | −177.4 (3) |
O2—C12—C13—C14 | −175.1 (3) | C26—C25—C30—C29 | −2.2 (5) |
N2—N1—C14—C13 | 0.1 (3) | N4—N3—C30—C25 | 0.4 (3) |
N2—N1—C14—S1 | −179.6 (2) | C22—N3—C30—C25 | 174.3 (3) |
C8—C13—C14—N1 | 0.4 (3) | N4—N3—C30—C29 | 177.6 (3) |
C12—C13—C14—N1 | 172.9 (3) | C22—N3—C30—C29 | −8.4 (5) |
C8—C13—C14—S1 | −179.9 (2) | C27—C29—C30—C25 | −18.4 (4) |
C12—C13—C14—S1 | −7.4 (5) | C27—C29—C30—N3 | 164.7 (3) |
Experimental details
Crystal data | |
Chemical formula | C15H14N2O3S |
Mr | 302.35 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 293 |
a, b, c (Å) | 24.083 (3), 7.393 (1), 18.820 (3) |
β (°) | 117.765 (2) |
V (Å3) | 2965.2 (7) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.38 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker APEX-II CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.725, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7700, 3972, 3298 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.083, 1.04 |
No. of reflections | 3972 |
No. of parameters | 383 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.15 |
Absolute structure | Flack (1983), 436 Friedel pairs |
Absolute structure parameter | −0.01 (7) |
Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
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.