



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536813020965/hb7109sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536813020965/hb7109Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536813020965/hb7109Isup3.cml |
CCDC reference: 964032
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.109
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 2.161 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.595 4
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF ? Do ! PLAT154_ALERT_1_G The su's on the Cell Angles are Equal .......... 0.00100 Deg. PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still 62 % PLAT961_ALERT_5_G Dataset Contains no Negative Intensities ....... ! Check
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 1 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 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
This compound was prepared according to the reported method (Mahabaleshwaraiah et al., 2012). Colourless needles were grown from a mixed solution of EtOH/CHCl3 (v/v = 2/1) by slow evaporation at room temperature. Yield = 88%, m.p. 441 K.
All H atoms were positioned geometrically, with C—H = 0.93 Å for aromatic H, C—H = 0.97 Å for methylene H and C—H = 0.96 Å for methyl H and refined using a riding model with Uiso(H) = 1.5Ueq(C) for methyl H and Uiso(H) = 1.2Ueq(C) for all other H.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![]() | Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. |
C16H15NO3S2 | Z = 4 |
Mr = 333.41 | F(000) = 696 |
Triclinic, P1 | Dx = 1.439 Mg m−3 |
Hall symbol: -P 1 | Melting point: 441 K |
a = 9.7158 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.5040 (2) Å | Cell parameters from 5420 reflections |
c = 13.5925 (2) Å | θ = 1.7–25.0° |
α = 106.415 (1)° | µ = 0.36 mm−1 |
β = 100.882 (1)° | T = 296 K |
γ = 94.854 (1)° | Plate, colourless |
V = 1538.74 (5) Å3 | 0.24 × 0.20 × 0.12 mm |
Bruker SMART CCD diffractometer | 5420 independent reflections |
Radiation source: fine-focus sealed tube | 4477 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω and ϕ scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −11→11 |
Tmin = 0.770, Tmax = 1.000 | k = −14→14 |
21575 measured reflections | l = −16→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0528P)2 + 0.3725P] where P = (Fo2 + 2Fc2)/3 |
5420 reflections | (Δ/σ)max = 0.001 |
397 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
C16H15NO3S2 | γ = 94.854 (1)° |
Mr = 333.41 | V = 1538.74 (5) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.7158 (2) Å | Mo Kα radiation |
b = 12.5040 (2) Å | µ = 0.36 mm−1 |
c = 13.5925 (2) Å | T = 296 K |
α = 106.415 (1)° | 0.24 × 0.20 × 0.12 mm |
β = 100.882 (1)° |
Bruker SMART CCD diffractometer | 5420 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 4477 reflections with I > 2σ(I) |
Tmin = 0.770, Tmax = 1.000 | Rint = 0.023 |
21575 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.109 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.34 e Å−3 |
5420 reflections | Δρmin = −0.38 e Å−3 |
397 parameters |
Experimental. IR (KBr): 636 cm-1(C—S), 1254 cm-1(C=S), 1070 cm-1(C—O), 854 cm-1 (C—N),1125 cm-1(C—O—C), 1694 cm-1 (C=O), 1731 cm-1(Coumarin C=O). GCMS: m/e: 335. 1H NMR (400 MHz, CDCl3, δ,. p.p.m): 2.11(m, 2H, Pyrrolidine-CH2) 2.16(m, 2H, Pyrrolidine-CH2), 3.68(t, 2H, Pyrrolidine-CH2), 3.91(t, 2H, Pyrrolidine-CH2),4.59(s, 2H, Methylene-CH2), 7.24(t, 1H, Ar—H), 7.41(d, 1H, Ar—H), 7.49(t, 1H, Ar—H), 7.65(d,1H, Ar—H),8.16(s, 1H, Ar—H). Elemental analysis for C16H15NO3S2: C, 57.58; H, 4.46; N, 4.13. |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | ||
S1B | 0.46924 (6) | 0.77672 (4) | 0.81900 (5) | 0.05885 (16) | |
S2B | 0.72066 (6) | 0.92077 (6) | 0.98610 (5) | 0.07162 (19) | |
O3B | 0.74479 (16) | 0.48705 (12) | 1.07902 (11) | 0.0598 (4) | |
O4B | 0.6049 (2) | 0.61413 (15) | 1.07471 (13) | 0.0813 (5) | |
O5B | 0.68855 (18) | 0.62686 (13) | 0.78589 (12) | 0.0704 (4) | |
N6B | 0.55263 (15) | 0.98720 (12) | 0.84624 (12) | 0.0455 (4) | |
C7B | 0.6776 (2) | 0.55533 (17) | 1.02806 (16) | 0.0566 (5) | |
C8B | 0.7036 (2) | 0.54840 (15) | 0.92381 (15) | 0.0470 (4) | |
C9B | 0.7859 (2) | 0.47448 (15) | 0.88210 (15) | 0.0474 (4) | |
H9B | 0.8008 | 0.4702 | 0.8156 | 0.057* | |
C10B | 0.85098 (19) | 0.40263 (15) | 0.93565 (15) | 0.0461 (4) | |
C11B | 0.8291 (2) | 0.41211 (16) | 1.03604 (15) | 0.0502 (5) | |
C12B | 0.8900 (2) | 0.34839 (19) | 1.09553 (18) | 0.0627 (6) | |
H12B | 0.8739 | 0.3559 | 1.1623 | 0.075* | |
C13B | 0.9745 (2) | 0.27392 (19) | 1.05399 (19) | 0.0652 (6) | |
H13B | 1.0165 | 0.2304 | 1.0931 | 0.078* | |
C14B | 0.9988 (2) | 0.26217 (17) | 0.95419 (18) | 0.0612 (5) | |
H14B | 1.0565 | 0.2110 | 0.9272 | 0.073* | |
C15B | 0.9378 (2) | 0.32573 (16) | 0.89536 (16) | 0.0549 (5) | |
H15B | 0.9543 | 0.3176 | 0.8286 | 0.066* | |
C16B | 0.6446 (2) | 0.62295 (15) | 0.86268 (16) | 0.0513 (5) | |
C17B | 0.5292 (3) | 0.68791 (18) | 0.89563 (19) | 0.0650 (6) | |
H17A | 0.5630 | 0.7342 | 0.9683 | 0.078* | |
H17B | 0.4489 | 0.6347 | 0.8928 | 0.078* | |
C18B | 0.58542 (19) | 0.90472 (16) | 0.88551 (15) | 0.0464 (4) | |
C19B | 0.4308 (2) | 0.97956 (16) | 0.76104 (17) | 0.0568 (5) | |
H19A | 0.3446 | 0.9454 | 0.7730 | 0.068* | |
H19B | 0.4458 | 0.9359 | 0.6936 | 0.068* | |
C20B | 0.4238 (3) | 1.10145 (19) | 0.7655 (2) | 0.0776 (7) | |
H20A | 0.3921 | 1.1074 | 0.6954 | 0.093* | |
H20B | 0.3588 | 1.1328 | 0.8082 | 0.093* | |
C21B | 0.5699 (3) | 1.16160 (18) | 0.8132 (2) | 0.0697 (6) | |
H21A | 0.5687 | 1.2402 | 0.8496 | 0.084* | |
H21B | 0.6245 | 1.1574 | 0.7597 | 0.084* | |
C22B | 0.6319 (2) | 1.10183 (16) | 0.88939 (17) | 0.0573 (5) | |
H22A | 0.7323 | 1.1007 | 0.8926 | 0.069* | |
H22B | 0.6185 | 1.1381 | 0.9594 | 0.069* | |
S1A | −0.04479 (6) | 0.82131 (5) | 0.38879 (5) | 0.06212 (17) | |
S2A | 0.26976 (7) | 0.90519 (6) | 0.46861 (6) | 0.0836 (2) | |
O3A | 0.24069 (18) | 0.53930 (13) | 0.65250 (11) | 0.0711 (4) | |
O4A | 0.1038 (2) | 0.66877 (16) | 0.64994 (13) | 0.0907 (6) | |
O5A | 0.0825 (2) | 0.61136 (15) | 0.32787 (13) | 0.0935 (6) | |
N6A | 0.09101 (16) | 0.98182 (13) | 0.34318 (13) | 0.0503 (4) | |
C7A | 0.1645 (3) | 0.60259 (19) | 0.59960 (17) | 0.0620 (5) | |
C8A | 0.1661 (2) | 0.57919 (16) | 0.48808 (15) | 0.0512 (5) | |
C9A | 0.2381 (2) | 0.49904 (15) | 0.44312 (15) | 0.0518 (5) | |
H9A | 0.2358 | 0.4836 | 0.3717 | 0.062* | |
C10A | 0.3180 (2) | 0.43666 (15) | 0.50018 (16) | 0.0507 (5) | |
C11A | 0.3162 (2) | 0.45940 (17) | 0.60620 (16) | 0.0585 (5) | |
C12A | 0.3893 (3) | 0.4023 (2) | 0.6678 (2) | 0.0774 (7) | |
H12A | 0.3854 | 0.4167 | 0.7381 | 0.093* | |
C13A | 0.4674 (3) | 0.3242 (2) | 0.6226 (2) | 0.0787 (7) | |
H13A | 0.5183 | 0.2861 | 0.6634 | 0.094* | |
C14A | 0.4726 (3) | 0.30032 (18) | 0.5179 (2) | 0.0698 (6) | |
H14A | 0.5268 | 0.2470 | 0.4891 | 0.084* | |
C15A | 0.3977 (2) | 0.35547 (16) | 0.45664 (18) | 0.0598 (5) | |
H15A | 0.4001 | 0.3387 | 0.3859 | 0.072* | |
C16A | 0.0888 (2) | 0.64165 (17) | 0.42166 (16) | 0.0582 (5) | |
C17A | 0.0179 (3) | 0.73924 (18) | 0.47142 (18) | 0.0632 (6) | |
H17C | 0.0847 | 0.7885 | 0.5333 | 0.076* | |
H17D | −0.0616 | 0.7101 | 0.4948 | 0.076* | |
C18A | 0.1125 (2) | 0.91016 (16) | 0.39811 (16) | 0.0524 (5) | |
C19A | −0.0455 (2) | 0.99070 (17) | 0.28054 (16) | 0.0546 (5) | |
H19C | −0.1066 | 1.0253 | 0.3253 | 0.065* | |
H19D | −0.0935 | 0.9172 | 0.2351 | 0.065* | |
C20A | −0.0040 (3) | 1.0652 (2) | 0.2166 (2) | 0.0765 (7) | |
H20C | 0.0106 | 1.0197 | 0.1497 | 0.092* | |
H20D | −0.0773 | 1.1107 | 0.2035 | 0.092* | |
C21A | 0.1297 (2) | 1.1377 (2) | 0.2816 (2) | 0.0690 (6) | |
H21C | 0.1099 | 1.2057 | 0.3291 | 0.083* | |
H21D | 0.1877 | 1.1587 | 0.2373 | 0.083* | |
C22A | 0.2031 (2) | 1.06729 (19) | 0.3421 (2) | 0.0672 (6) | |
H22C | 0.2740 | 1.0322 | 0.3078 | 0.081* | |
H22D | 0.2489 | 1.1131 | 0.4132 | 0.081* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1B | 0.0681 (3) | 0.0498 (3) | 0.0632 (4) | 0.0148 (2) | 0.0129 (3) | 0.0236 (2) |
S2B | 0.0666 (4) | 0.0952 (4) | 0.0564 (4) | 0.0269 (3) | −0.0002 (3) | 0.0330 (3) |
O3B | 0.0772 (9) | 0.0722 (9) | 0.0451 (8) | 0.0197 (7) | 0.0246 (7) | 0.0319 (7) |
O4B | 0.1223 (14) | 0.0904 (11) | 0.0576 (10) | 0.0506 (11) | 0.0490 (10) | 0.0349 (9) |
O5B | 0.1029 (12) | 0.0805 (10) | 0.0563 (9) | 0.0452 (9) | 0.0402 (9) | 0.0419 (8) |
N6B | 0.0439 (8) | 0.0489 (8) | 0.0451 (9) | 0.0114 (6) | 0.0063 (7) | 0.0177 (7) |
C7B | 0.0768 (14) | 0.0566 (11) | 0.0469 (12) | 0.0160 (10) | 0.0236 (10) | 0.0238 (10) |
C8B | 0.0619 (11) | 0.0454 (10) | 0.0391 (10) | 0.0085 (8) | 0.0164 (9) | 0.0181 (8) |
C9B | 0.0622 (11) | 0.0472 (10) | 0.0358 (10) | 0.0058 (8) | 0.0132 (8) | 0.0168 (8) |
C10B | 0.0550 (10) | 0.0449 (9) | 0.0404 (10) | 0.0045 (8) | 0.0087 (8) | 0.0180 (8) |
C11B | 0.0556 (11) | 0.0541 (11) | 0.0460 (11) | 0.0041 (9) | 0.0133 (9) | 0.0233 (9) |
C12B | 0.0713 (13) | 0.0773 (14) | 0.0518 (13) | 0.0088 (11) | 0.0137 (10) | 0.0398 (11) |
C13B | 0.0685 (13) | 0.0698 (14) | 0.0658 (15) | 0.0113 (11) | 0.0043 (11) | 0.0407 (12) |
C14B | 0.0667 (13) | 0.0572 (12) | 0.0635 (14) | 0.0165 (10) | 0.0085 (11) | 0.0260 (11) |
C15B | 0.0667 (12) | 0.0539 (11) | 0.0458 (12) | 0.0113 (9) | 0.0098 (9) | 0.0191 (9) |
C16B | 0.0695 (12) | 0.0454 (10) | 0.0445 (11) | 0.0122 (9) | 0.0195 (10) | 0.0168 (9) |
C17B | 0.0857 (15) | 0.0598 (12) | 0.0717 (15) | 0.0276 (11) | 0.0369 (12) | 0.0374 (11) |
C18B | 0.0490 (10) | 0.0569 (11) | 0.0417 (10) | 0.0206 (8) | 0.0177 (8) | 0.0195 (9) |
C19B | 0.0535 (11) | 0.0582 (11) | 0.0579 (13) | 0.0092 (9) | −0.0022 (9) | 0.0259 (10) |
C20B | 0.0760 (15) | 0.0692 (14) | 0.0923 (19) | 0.0148 (12) | −0.0030 (13) | 0.0449 (14) |
C21B | 0.0829 (16) | 0.0533 (12) | 0.0761 (16) | 0.0101 (11) | 0.0146 (13) | 0.0267 (11) |
C22B | 0.0589 (12) | 0.0525 (11) | 0.0567 (13) | 0.0043 (9) | 0.0088 (10) | 0.0146 (10) |
S1A | 0.0642 (3) | 0.0604 (3) | 0.0718 (4) | 0.0186 (2) | 0.0199 (3) | 0.0301 (3) |
S2A | 0.0641 (4) | 0.1074 (5) | 0.0888 (5) | 0.0289 (3) | 0.0023 (3) | 0.0495 (4) |
O3A | 0.1042 (12) | 0.0781 (10) | 0.0399 (8) | 0.0224 (9) | 0.0178 (8) | 0.0279 (8) |
O4A | 0.1331 (16) | 0.1087 (14) | 0.0493 (10) | 0.0566 (12) | 0.0395 (10) | 0.0302 (10) |
O5A | 0.1646 (18) | 0.0908 (12) | 0.0433 (10) | 0.0714 (12) | 0.0306 (10) | 0.0290 (9) |
N6A | 0.0475 (8) | 0.0547 (9) | 0.0514 (10) | 0.0140 (7) | 0.0102 (7) | 0.0191 (8) |
C7A | 0.0842 (15) | 0.0650 (13) | 0.0432 (12) | 0.0146 (11) | 0.0165 (11) | 0.0240 (10) |
C8A | 0.0678 (12) | 0.0491 (10) | 0.0382 (11) | 0.0061 (9) | 0.0128 (9) | 0.0161 (9) |
C9A | 0.0715 (13) | 0.0500 (10) | 0.0363 (10) | 0.0061 (9) | 0.0115 (9) | 0.0183 (9) |
C10A | 0.0598 (11) | 0.0456 (10) | 0.0464 (11) | −0.0001 (8) | 0.0059 (9) | 0.0195 (9) |
C11A | 0.0740 (13) | 0.0546 (11) | 0.0458 (12) | 0.0018 (10) | 0.0046 (10) | 0.0216 (10) |
C12A | 0.1071 (19) | 0.0735 (15) | 0.0520 (14) | 0.0074 (14) | −0.0004 (13) | 0.0332 (12) |
C13A | 0.0972 (18) | 0.0650 (14) | 0.0736 (18) | 0.0093 (13) | −0.0082 (14) | 0.0393 (13) |
C14A | 0.0748 (14) | 0.0555 (12) | 0.0796 (18) | 0.0122 (10) | 0.0044 (12) | 0.0292 (12) |
C15A | 0.0723 (13) | 0.0510 (11) | 0.0575 (13) | 0.0070 (10) | 0.0085 (11) | 0.0233 (10) |
C16A | 0.0842 (15) | 0.0558 (11) | 0.0418 (12) | 0.0196 (10) | 0.0203 (10) | 0.0192 (9) |
C17A | 0.0853 (15) | 0.0601 (12) | 0.0555 (13) | 0.0197 (11) | 0.0271 (11) | 0.0256 (11) |
C18A | 0.0589 (11) | 0.0550 (11) | 0.0463 (11) | 0.0226 (9) | 0.0147 (9) | 0.0142 (9) |
C19A | 0.0530 (11) | 0.0556 (11) | 0.0536 (12) | 0.0135 (9) | 0.0046 (9) | 0.0175 (10) |
C20A | 0.0835 (16) | 0.0745 (15) | 0.0727 (17) | 0.0067 (12) | 0.0010 (13) | 0.0364 (13) |
C21A | 0.0718 (14) | 0.0744 (14) | 0.0741 (16) | 0.0134 (11) | 0.0256 (12) | 0.0365 (13) |
C22A | 0.0547 (12) | 0.0714 (14) | 0.0800 (17) | 0.0060 (10) | 0.0163 (11) | 0.0301 (12) |
S1B—C18B | 1.773 (2) | S1A—C18A | 1.774 (2) |
S1B—C17B | 1.787 (2) | S1A—C17A | 1.785 (2) |
S2B—C18B | 1.6608 (19) | S2A—C18A | 1.659 (2) |
O3B—C11B | 1.375 (2) | O3A—C11A | 1.370 (3) |
O3B—C7B | 1.376 (2) | O3A—C7A | 1.382 (2) |
O4B—C7B | 1.198 (2) | O4A—C7A | 1.190 (3) |
O5B—C16B | 1.211 (2) | O5A—C16A | 1.211 (2) |
N6B—C18B | 1.324 (2) | N6A—C18A | 1.325 (2) |
N6B—C19B | 1.467 (2) | N6A—C22A | 1.465 (3) |
N6B—C22B | 1.469 (2) | N6A—C19A | 1.466 (2) |
C7B—C8B | 1.466 (3) | C7A—C8A | 1.464 (3) |
C8B—C9B | 1.348 (3) | C8A—C9A | 1.342 (3) |
C8B—C16B | 1.495 (3) | C8A—C16A | 1.494 (3) |
C9B—C10B | 1.424 (2) | C9A—C10A | 1.425 (3) |
C9B—H9B | 0.9300 | C9A—H9A | 0.9300 |
C10B—C11B | 1.394 (3) | C10A—C11A | 1.392 (3) |
C10B—C15B | 1.396 (3) | C10A—C15A | 1.395 (3) |
C11B—C12B | 1.379 (3) | C11A—C12A | 1.383 (3) |
C12B—C13B | 1.367 (3) | C12A—C13A | 1.368 (4) |
C12B—H12B | 0.9300 | C12A—H12A | 0.9300 |
C13B—C14B | 1.390 (3) | C13A—C14A | 1.381 (4) |
C13B—H13B | 0.9300 | C13A—H13A | 0.9300 |
C14B—C15B | 1.372 (3) | C14A—C15A | 1.371 (3) |
C14B—H14B | 0.9300 | C14A—H14A | 0.9300 |
C15B—H15B | 0.9300 | C15A—H15A | 0.9300 |
C16B—C17B | 1.502 (3) | C16A—C17A | 1.507 (3) |
C17B—H17A | 0.9700 | C17A—H17C | 0.9700 |
C17B—H17B | 0.9700 | C17A—H17D | 0.9700 |
C19B—C20B | 1.516 (3) | C19A—C20A | 1.520 (3) |
C19B—H19A | 0.9700 | C19A—H19C | 0.9700 |
C19B—H19B | 0.9700 | C19A—H19D | 0.9700 |
C20B—C21B | 1.483 (3) | C20A—C21A | 1.485 (3) |
C20B—H20A | 0.9700 | C20A—H20C | 0.9700 |
C20B—H20B | 0.9700 | C20A—H20D | 0.9700 |
C21B—C22B | 1.507 (3) | C21A—C22A | 1.501 (3) |
C21B—H21A | 0.9700 | C21A—H21C | 0.9700 |
C21B—H21B | 0.9700 | C21A—H21D | 0.9700 |
C22B—H22A | 0.9700 | C22A—H22C | 0.9700 |
C22B—H22B | 0.9700 | C22A—H22D | 0.9700 |
C18B—S1B—C17B | 102.01 (11) | C18A—S1A—C17A | 101.77 (10) |
C11B—O3B—C7B | 123.64 (15) | C11A—O3A—C7A | 123.44 (16) |
C18B—N6B—C19B | 125.64 (16) | C18A—N6A—C22A | 123.09 (17) |
C18B—N6B—C22B | 122.64 (16) | C18A—N6A—C19A | 125.71 (17) |
C19B—N6B—C22B | 111.60 (14) | C22A—N6A—C19A | 111.15 (16) |
O4B—C7B—O3B | 115.83 (18) | O4A—C7A—O3A | 116.01 (19) |
O4B—C7B—C8B | 127.55 (19) | O4A—C7A—C8A | 127.7 (2) |
O3B—C7B—C8B | 116.62 (17) | O3A—C7A—C8A | 116.33 (19) |
C9B—C8B—C7B | 119.33 (17) | C9A—C8A—C7A | 119.63 (18) |
C9B—C8B—C16B | 118.46 (16) | C9A—C8A—C16A | 118.44 (17) |
C7B—C8B—C16B | 122.20 (17) | C7A—C8A—C16A | 121.92 (18) |
C8B—C9B—C10B | 122.74 (17) | C8A—C9A—C10A | 122.76 (18) |
C8B—C9B—H9B | 118.6 | C8A—C9A—H9A | 118.6 |
C10B—C9B—H9B | 118.6 | C10A—C9A—H9A | 118.6 |
C11B—C10B—C15B | 118.09 (17) | C11A—C10A—C15A | 118.51 (19) |
C11B—C10B—C9B | 117.53 (17) | C11A—C10A—C9A | 117.30 (19) |
C15B—C10B—C9B | 124.36 (17) | C15A—C10A—C9A | 124.19 (19) |
O3B—C11B—C12B | 117.76 (18) | O3A—C11A—C12A | 118.0 (2) |
O3B—C11B—C10B | 120.10 (16) | O3A—C11A—C10A | 120.50 (18) |
C12B—C11B—C10B | 122.14 (19) | C12A—C11A—C10A | 121.5 (2) |
C13B—C12B—C11B | 118.4 (2) | C13A—C12A—C11A | 118.2 (2) |
C13B—C12B—H12B | 120.8 | C13A—C12A—H12A | 120.9 |
C11B—C12B—H12B | 120.8 | C11A—C12A—H12A | 120.9 |
C12B—C13B—C14B | 121.07 (19) | C12A—C13A—C14A | 121.7 (2) |
C12B—C13B—H13B | 119.5 | C12A—C13A—H13A | 119.1 |
C14B—C13B—H13B | 119.5 | C14A—C13A—H13A | 119.1 |
C15B—C14B—C13B | 120.3 (2) | C15A—C14A—C13A | 119.8 (2) |
C15B—C14B—H14B | 119.9 | C15A—C14A—H14A | 120.1 |
C13B—C14B—H14B | 119.9 | C13A—C14A—H14A | 120.1 |
C14B—C15B—C10B | 120.04 (19) | C14A—C15A—C10A | 120.2 (2) |
C14B—C15B—H15B | 120.0 | C14A—C15A—H15A | 119.9 |
C10B—C15B—H15B | 120.0 | C10A—C15A—H15A | 119.9 |
O5B—C16B—C8B | 118.99 (17) | O5A—C16A—C8A | 118.90 (18) |
O5B—C16B—C17B | 121.65 (18) | O5A—C16A—C17A | 121.16 (19) |
C8B—C16B—C17B | 119.33 (17) | C8A—C16A—C17A | 119.93 (17) |
C16B—C17B—S1B | 115.66 (15) | C16A—C17A—S1A | 115.49 (15) |
C16B—C17B—H17A | 108.4 | C16A—C17A—H17C | 108.4 |
S1B—C17B—H17A | 108.4 | S1A—C17A—H17C | 108.4 |
C16B—C17B—H17B | 108.4 | C16A—C17A—H17D | 108.4 |
S1B—C17B—H17B | 108.4 | S1A—C17A—H17D | 108.4 |
H17A—C17B—H17B | 107.4 | H17C—C17A—H17D | 107.5 |
N6B—C18B—S2B | 123.21 (15) | N6A—C18A—S2A | 123.39 (16) |
N6B—C18B—S1B | 112.52 (14) | N6A—C18A—S1A | 112.74 (14) |
S2B—C18B—S1B | 124.27 (11) | S2A—C18A—S1A | 123.87 (12) |
N6B—C19B—C20B | 103.42 (16) | N6A—C19A—C20A | 103.19 (17) |
N6B—C19B—H19A | 111.1 | N6A—C19A—H19C | 111.1 |
C20B—C19B—H19A | 111.1 | C20A—C19A—H19C | 111.1 |
N6B—C19B—H19B | 111.1 | N6A—C19A—H19D | 111.1 |
C20B—C19B—H19B | 111.1 | C20A—C19A—H19D | 111.1 |
H19A—C19B—H19B | 109.0 | H19C—C19A—H19D | 109.1 |
C21B—C20B—C19B | 105.75 (17) | C21A—C20A—C19A | 105.50 (19) |
C21B—C20B—H20A | 110.6 | C21A—C20A—H20C | 110.6 |
C19B—C20B—H20A | 110.6 | C19A—C20A—H20C | 110.6 |
C21B—C20B—H20B | 110.6 | C21A—C20A—H20D | 110.6 |
C19B—C20B—H20B | 110.6 | C19A—C20A—H20D | 110.6 |
H20A—C20B—H20B | 108.7 | H20C—C20A—H20D | 108.8 |
C20B—C21B—C22B | 105.07 (18) | C20A—C21A—C22A | 105.23 (18) |
C20B—C21B—H21A | 110.7 | C20A—C21A—H21C | 110.7 |
C22B—C21B—H21A | 110.7 | C22A—C21A—H21C | 110.7 |
C20B—C21B—H21B | 110.7 | C20A—C21A—H21D | 110.7 |
C22B—C21B—H21B | 110.7 | C22A—C21A—H21D | 110.7 |
H21A—C21B—H21B | 108.8 | H21C—C21A—H21D | 108.8 |
N6B—C22B—C21B | 104.04 (16) | N6A—C22A—C21A | 105.22 (17) |
N6B—C22B—H22A | 110.9 | N6A—C22A—H22C | 110.7 |
C21B—C22B—H22A | 110.9 | C21A—C22A—H22C | 110.7 |
N6B—C22B—H22B | 110.9 | N6A—C22A—H22D | 110.7 |
C21B—C22B—H22B | 110.9 | C21A—C22A—H22D | 110.7 |
H22A—C22B—H22B | 109.0 | H22C—C22A—H22D | 108.8 |
C11B—O3B—C7B—O4B | 178.2 (2) | C11A—O3A—C7A—O4A | 179.9 (2) |
C11B—O3B—C7B—C8B | −2.1 (3) | C11A—O3A—C7A—C8A | 0.8 (3) |
O4B—C7B—C8B—C9B | −178.1 (2) | O4A—C7A—C8A—C9A | −178.3 (2) |
O3B—C7B—C8B—C9B | 2.3 (3) | O3A—C7A—C8A—C9A | 0.6 (3) |
O4B—C7B—C8B—C16B | 3.5 (4) | O4A—C7A—C8A—C16A | 1.3 (4) |
O3B—C7B—C8B—C16B | −176.11 (17) | O3A—C7A—C8A—C16A | −179.78 (18) |
C7B—C8B—C9B—C10B | −0.7 (3) | C7A—C8A—C9A—C10A | −1.9 (3) |
C16B—C8B—C9B—C10B | 177.76 (17) | C16A—C8A—C9A—C10A | 178.45 (18) |
C8B—C9B—C10B—C11B | −1.1 (3) | C8A—C9A—C10A—C11A | 1.8 (3) |
C8B—C9B—C10B—C15B | −179.45 (19) | C8A—C9A—C10A—C15A | −177.80 (19) |
C7B—O3B—C11B—C12B | −179.84 (18) | C7A—O3A—C11A—C12A | 179.4 (2) |
C7B—O3B—C11B—C10B | 0.3 (3) | C7A—O3A—C11A—C10A | −0.9 (3) |
C15B—C10B—C11B—O3B | 179.76 (17) | C15A—C10A—C11A—O3A | 179.27 (18) |
C9B—C10B—C11B—O3B | 1.3 (3) | C9A—C10A—C11A—O3A | −0.4 (3) |
C15B—C10B—C11B—C12B | 0.0 (3) | C15A—C10A—C11A—C12A | −1.0 (3) |
C9B—C10B—C11B—C12B | −178.46 (18) | C9A—C10A—C11A—C12A | 179.3 (2) |
O3B—C11B—C12B—C13B | −179.70 (19) | O3A—C11A—C12A—C13A | −178.6 (2) |
C10B—C11B—C12B—C13B | 0.1 (3) | C10A—C11A—C12A—C13A | 1.7 (4) |
C11B—C12B—C13B—C14B | −0.1 (3) | C11A—C12A—C13A—C14A | −1.1 (4) |
C12B—C13B—C14B—C15B | 0.1 (3) | C12A—C13A—C14A—C15A | −0.2 (4) |
C13B—C14B—C15B—C10B | 0.0 (3) | C13A—C14A—C15A—C10A | 0.9 (3) |
C11B—C10B—C15B—C14B | 0.0 (3) | C11A—C10A—C15A—C14A | −0.3 (3) |
C9B—C10B—C15B—C14B | 178.29 (18) | C9A—C10A—C15A—C14A | 179.32 (19) |
C9B—C8B—C16B—O5B | −10.7 (3) | C9A—C8A—C16A—O5A | 6.7 (3) |
C7B—C8B—C16B—O5B | 167.7 (2) | C7A—C8A—C16A—O5A | −172.9 (2) |
C9B—C8B—C16B—C17B | 167.16 (19) | C9A—C8A—C16A—C17A | −174.44 (19) |
C7B—C8B—C16B—C17B | −14.4 (3) | C7A—C8A—C16A—C17A | 6.0 (3) |
O5B—C16B—C17B—S1B | −3.5 (3) | O5A—C16A—C17A—S1A | −11.3 (3) |
C8B—C16B—C17B—S1B | 178.68 (15) | C8A—C16A—C17A—S1A | 169.88 (16) |
C18B—S1B—C17B—C16B | −89.01 (19) | C18A—S1A—C17A—C16A | −80.90 (19) |
C19B—N6B—C18B—S2B | −176.91 (15) | C22A—N6A—C18A—S2A | −2.4 (3) |
C22B—N6B—C18B—S2B | −1.1 (3) | C19A—N6A—C18A—S2A | −179.34 (15) |
C19B—N6B—C18B—S1B | 3.0 (2) | C22A—N6A—C18A—S1A | 177.18 (16) |
C22B—N6B—C18B—S1B | 178.87 (14) | C19A—N6A—C18A—S1A | 0.2 (2) |
C17B—S1B—C18B—N6B | −175.02 (14) | C17A—S1A—C18A—N6A | −178.87 (15) |
C17B—S1B—C18B—S2B | 4.90 (15) | C17A—S1A—C18A—S2A | 0.69 (16) |
C18B—N6B—C19B—C20B | 167.00 (19) | C18A—N6A—C19A—C20A | −167.79 (19) |
C22B—N6B—C19B—C20B | −9.2 (2) | C22A—N6A—C19A—C20A | 15.0 (2) |
N6B—C19B—C20B—C21B | 25.7 (3) | N6A—C19A—C20A—C21A | −28.4 (2) |
C19B—C20B—C21B—C22B | −32.7 (3) | C19A—C20A—C21A—C22A | 31.4 (3) |
C18B—N6B—C22B—C21B | 173.23 (18) | C18A—N6A—C22A—C21A | −173.35 (19) |
C19B—N6B—C22B—C21B | −10.4 (2) | C19A—N6A—C22A—C21A | 4.0 (2) |
C20B—C21B—C22B—N6B | 26.3 (2) | C20A—C21A—C22A—N6A | −21.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9A—H9A···O5Bi | 0.93 | 2.48 | 3.307 (2) | 149 |
C15A—H15A···O5Bi | 0.93 | 2.50 | 3.319 (3) | 147 |
C9B—H9B···O5Ai | 0.93 | 2.46 | 3.288 (3) | 149 |
C15B—H15B···O5Ai | 0.93 | 2.50 | 3.319 (3) | 146 |
C17B—H17B···O3Bii | 0.97 | 2.47 | 3.432 (3) | 170 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9A—H9A···O5Bi | 0.93 | 2.48 | 3.307 (2) | 149 |
C15A—H15A···O5Bi | 0.93 | 2.50 | 3.319 (3) | 147 |
C9B—H9B···O5Ai | 0.93 | 2.46 | 3.288 (3) | 149 |
C15B—H15B···O5Ai | 0.93 | 2.50 | 3.319 (3) | 146 |
C17B—H17B···O3Bii | 0.97 | 2.47 | 3.432 (3) | 170 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z+2. |
As part of our ongoing structural studies of coumarin derivatives with possible biological activity (Mahabaleshwaraiah et al., 2012), we now describe the structure of the title compound, (I).
There are two independent molecules in the asymmetric unit of 2-oxo-2- (2-oxo-2H-chromen-3-yl)ethyl pyrrolidine-1-carbodithioate is shown in Fig. 1. The 2H-chromene ring systems (O3a/C7a–C15a) and (O3b/C7b–C15b) are nearly planar, with a maximum deviation of 0.0167 (20) Å and 0.0136 (19) Å respectively. The pyrrolidine rings (N6a/C19a—C22a) and (N6b/C19b—C22b) are not coplanar with the 2H-chromene ring systems (O3a/C7a–C15a) and (O3b/C7b–C15b); the dihedral angles between two planes being 83.83 (11)° and 82.43 (11)° in the two molecules. In the crystal, inversion related C17B—H17B···O3B hydrogen bonds generate R22(12) loops.