Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023914/hk2248sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023914/hk2248Isup2.hkl |
CCDC reference: 651493
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.004 Å
- R factor = 0.060
- wR factor = 0.159
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.118 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C10 .. 5.64 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound, (I), was synthesized according to the literature method (Huang et al., 2005). Crystals suitable for X-ray analysis were grown from dichloromethane at 277 K.
H atoms were positioned geometrically, with C—H = 0.93 Å for aromatic H, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).
Flavonoids, occurring widely throughout the plant kingdom, are one of the most representative families of plant secondary metabolites and display a remarkable spectrum of biological activities. They are one of the most important groups of biological compounds in nature, and are used as a synthetic lead for drug discovery (Ren et al., 2003; Kim et al., 2004). The title compound, (I), is a flavonoid derivative with bioactive heterocyclic thioether subunit. We herein report its crystal structure.
In the molecule of the title compound, (I), (Fig. 1), the bond lengths and angles are generally within normal ranges (Allen et al., 1987).
The rings A (C1—C6), B (O1/C1/C6—C9), C (N1/O3/C10/C11/C16) and D (C11—C16) are, of course, planar and the dihedral angles between them are A/B = 1.0 (1)° and C/D = 1.0 (1)°. So, the rings A, B and C, D are coplanar and they are also oriented at a dihedral angle of 78.0 (1)°.
In the crystal structure, the intermolecular C—H···O hydrogen bonds link the molecules into chains along the b axis (Fig. 2), in which they may be effective in the stabilization of the structure. Further stability is provided by the offset π-π stacking interactions (Janiak, 2000) involving the adjacent coplanar rings C and D with centroid···centroid (symmetry code: 1 - x, 1 - y, 1 - z) distance of 3.89 (1) Å, beside of the adjacent D rings with centroid···centroid (symmetry code: 1 - x, -y, 1 - z) distance of 3.93 (1) Å.
For general backgroud, see: Ren et al. (2003); Kim et al. (2004); Allen et al. (1987); Janiak (2000). For related literature, see: Huang et al. (2005).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2001).
C16H9NO3S | F(000) = 608 |
Mr = 295.30 | Dx = 1.515 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2673 reflections |
a = 13.3357 (10) Å | θ = 2.8–25.4° |
b = 6.7749 (5) Å | µ = 0.26 mm−1 |
c = 15.0185 (11) Å | T = 291 K |
β = 107.417 (1)° | Plate, yellow |
V = 1294.68 (17) Å3 | 0.20 × 0.20 × 0.10 mm |
Z = 4 |
Bruker SMART 4K CCD area-detector diffractometer | 2128 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.118 |
Graphite monochromator | θmax = 27.5°, θmin = 1.6° |
φ and ω scans | h = −17→14 |
9560 measured reflections | k = −8→8 |
2939 independent reflections | l = −19→17 |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0811P)2] where P = (Fo2 + 2Fc2)/3 |
2939 reflections | (Δ/σ)max < 0.001 |
190 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
C16H9NO3S | V = 1294.68 (17) Å3 |
Mr = 295.30 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.3357 (10) Å | µ = 0.26 mm−1 |
b = 6.7749 (5) Å | T = 291 K |
c = 15.0185 (11) Å | 0.20 × 0.20 × 0.10 mm |
β = 107.417 (1)° |
Bruker SMART 4K CCD area-detector diffractometer | 2128 reflections with I > 2σ(I) |
9560 measured reflections | Rint = 0.118 |
2939 independent reflections |
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.45 e Å−3 |
2939 reflections | Δρmin = −0.35 e Å−3 |
190 parameters |
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 | 0.25607 (5) | 0.15017 (9) | 0.31455 (4) | 0.0564 (2) | |
O1 | 0.00612 (12) | −0.0770 (2) | 0.36603 (10) | 0.0529 (4) | |
O2 | 0.11610 (13) | 0.4808 (2) | 0.35113 (11) | 0.0617 (5) | |
O3 | 0.44360 (12) | 0.2234 (2) | 0.42736 (11) | 0.0546 (4) | |
N1 | 0.32159 (15) | 0.2063 (3) | 0.50334 (13) | 0.0501 (5) | |
C1 | −0.01555 (17) | 0.2751 (3) | 0.37804 (13) | 0.0429 (5) | |
C2 | −0.07754 (18) | 0.4293 (4) | 0.39490 (15) | 0.0529 (6) | |
H2 | −0.0564 | 0.5596 | 0.3928 | 0.064* | |
C3 | −0.1697 (2) | 0.3877 (4) | 0.41463 (17) | 0.0632 (7) | |
H3 | −0.2107 | 0.4899 | 0.4263 | 0.076* | |
C4 | −0.2016 (2) | 0.1924 (4) | 0.41714 (17) | 0.0645 (7) | |
H4 | −0.2641 | 0.1663 | 0.4304 | 0.077* | |
C5 | −0.14377 (18) | 0.0390 (4) | 0.40063 (16) | 0.0558 (6) | |
H5 | −0.1657 | −0.0909 | 0.4025 | 0.067* | |
C6 | −0.05054 (18) | 0.0830 (3) | 0.38089 (14) | 0.0463 (5) | |
C7 | 0.09752 (18) | −0.0436 (3) | 0.34882 (14) | 0.0490 (5) | |
H7 | 0.1357 | −0.1527 | 0.3399 | 0.059* | |
C8 | 0.13791 (17) | 0.1350 (3) | 0.34352 (15) | 0.0447 (5) | |
C9 | 0.08359 (18) | 0.3143 (3) | 0.35709 (14) | 0.0444 (5) | |
C10 | 0.34169 (17) | 0.1960 (3) | 0.42519 (16) | 0.0487 (6) | |
C11 | 0.49506 (18) | 0.2573 (3) | 0.52130 (17) | 0.0509 (6) | |
C12 | 0.5994 (2) | 0.3002 (4) | 0.5648 (2) | 0.0646 (7) | |
H12 | 0.6483 | 0.3096 | 0.5319 | 0.078* | |
C13 | 0.6269 (2) | 0.3284 (4) | 0.6604 (2) | 0.0710 (8) | |
H13 | 0.6963 | 0.3577 | 0.6929 | 0.085* | |
C14 | 0.5543 (2) | 0.3142 (4) | 0.7084 (2) | 0.0735 (8) | |
H14 | 0.5762 | 0.3313 | 0.7728 | 0.088* | |
C15 | 0.4496 (2) | 0.2751 (4) | 0.66347 (19) | 0.0678 (7) | |
H15 | 0.4005 | 0.2684 | 0.6962 | 0.081* | |
C16 | 0.42064 (18) | 0.2463 (3) | 0.56834 (16) | 0.0496 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0623 (4) | 0.0622 (4) | 0.0489 (4) | 0.0040 (3) | 0.0232 (3) | −0.0020 (3) |
O1 | 0.0595 (10) | 0.0400 (8) | 0.0574 (10) | −0.0033 (7) | 0.0149 (8) | −0.0003 (7) |
O2 | 0.0705 (12) | 0.0417 (9) | 0.0777 (12) | −0.0042 (8) | 0.0298 (9) | −0.0009 (8) |
O3 | 0.0522 (10) | 0.0552 (9) | 0.0646 (11) | 0.0072 (7) | 0.0298 (8) | 0.0047 (8) |
N1 | 0.0469 (11) | 0.0583 (11) | 0.0484 (11) | −0.0007 (9) | 0.0194 (9) | 0.0017 (9) |
C1 | 0.0502 (13) | 0.0444 (11) | 0.0315 (11) | 0.0013 (9) | 0.0081 (9) | −0.0007 (8) |
C2 | 0.0617 (15) | 0.0492 (12) | 0.0482 (13) | 0.0050 (11) | 0.0170 (11) | 0.0012 (10) |
C3 | 0.0627 (17) | 0.0728 (17) | 0.0538 (15) | 0.0159 (14) | 0.0169 (12) | −0.0026 (12) |
C4 | 0.0550 (15) | 0.088 (2) | 0.0516 (15) | −0.0049 (14) | 0.0172 (12) | −0.0011 (13) |
C5 | 0.0549 (15) | 0.0601 (15) | 0.0506 (13) | −0.0097 (11) | 0.0130 (11) | 0.0018 (11) |
C6 | 0.0542 (13) | 0.0460 (11) | 0.0330 (11) | −0.0025 (10) | 0.0044 (9) | −0.0001 (9) |
C7 | 0.0578 (14) | 0.0416 (12) | 0.0444 (12) | 0.0044 (10) | 0.0105 (10) | −0.0010 (9) |
C8 | 0.0512 (13) | 0.0432 (11) | 0.0375 (11) | 0.0009 (9) | 0.0099 (9) | −0.0014 (8) |
C9 | 0.0549 (13) | 0.0406 (11) | 0.0349 (11) | −0.0007 (9) | 0.0094 (9) | 0.0022 (8) |
C10 | 0.0489 (14) | 0.0415 (11) | 0.0592 (15) | 0.0062 (9) | 0.0215 (11) | 0.0046 (10) |
C11 | 0.0477 (13) | 0.0412 (11) | 0.0655 (16) | 0.0082 (9) | 0.0197 (11) | 0.0070 (10) |
C12 | 0.0466 (14) | 0.0549 (14) | 0.098 (2) | 0.0088 (11) | 0.0299 (14) | 0.0077 (14) |
C13 | 0.0525 (16) | 0.0570 (15) | 0.092 (2) | 0.0069 (12) | 0.0039 (15) | −0.0015 (14) |
C14 | 0.0648 (18) | 0.0763 (19) | 0.0681 (19) | 0.0070 (14) | 0.0030 (15) | −0.0031 (14) |
C15 | 0.0619 (17) | 0.0843 (19) | 0.0571 (16) | 0.0021 (14) | 0.0176 (13) | 0.0028 (13) |
C16 | 0.0475 (13) | 0.0504 (13) | 0.0542 (14) | 0.0050 (10) | 0.0203 (11) | 0.0048 (10) |
S1—C10 | 1.739 (2) | C4—C5 | 1.361 (4) |
S1—C8 | 1.759 (2) | C6—C5 | 1.394 (3) |
O1—C6 | 1.378 (3) | C7—H7 | 0.9300 |
O1—C7 | 1.339 (3) | C8—C7 | 1.337 (3) |
O3—C10 | 1.362 (3) | C8—C9 | 1.460 (3) |
O3—C11 | 1.391 (3) | C9—O2 | 1.221 (2) |
N1—C10 | 1.282 (3) | C11—C12 | 1.380 (4) |
N1—C16 | 1.414 (3) | C11—C12 | 1.380 (4) |
C1—C2 | 1.401 (3) | C12—H12 | 0.9300 |
C1—C6 | 1.387 (3) | C13—C12 | 1.384 (4) |
C1—C9 | 1.472 (3) | C13—H13 | 0.9300 |
C2—C3 | 1.377 (3) | C13—C14 | 1.373 (4) |
C2—H2 | 0.9300 | C14—H14 | 0.9300 |
C5—H5 | 0.9300 | C14—C15 | 1.383 (4) |
C3—H3 | 0.9300 | C15—H15 | 0.9300 |
C4—C3 | 1.394 (4) | C16—C11 | 1.382 (3) |
C4—H4 | 0.9300 | C16—C15 | 1.378 (3) |
C10—S1—C8 | 98.90 (10) | C7—C8—S1 | 118.32 (17) |
C7—O1—C6 | 118.26 (16) | C9—C8—S1 | 120.31 (16) |
C10—O3—C11 | 103.44 (16) | O2—C9—C8 | 123.8 (2) |
C10—N1—C16 | 103.55 (18) | O2—C9—C1 | 122.9 (2) |
C6—C1—C2 | 118.1 (2) | C8—C9—C1 | 113.23 (18) |
C6—C1—C9 | 120.54 (19) | N1—C10—O3 | 116.8 (2) |
C2—C1—C9 | 121.3 (2) | N1—C10—S1 | 128.83 (18) |
C3—C2—C1 | 120.0 (2) | O3—C10—S1 | 114.33 (16) |
C3—C2—H2 | 120.0 | C12—C11—C16 | 123.1 (2) |
C1—C2—H2 | 120.0 | C12—C11—O3 | 129.5 (2) |
C2—C3—C4 | 120.0 (2) | C16—C11—O3 | 107.3 (2) |
C2—C3—H3 | 120.0 | C11—C12—C13 | 115.9 (2) |
C4—C3—H3 | 120.0 | C11—C12—H12 | 122.1 |
C5—C4—C3 | 121.7 (2) | C13—C12—H12 | 122.1 |
C5—C4—H4 | 119.1 | C14—C13—C12 | 121.7 (3) |
C3—C4—H4 | 119.1 | C14—C13—H13 | 119.1 |
C4—C5—C6 | 117.8 (2) | C12—C13—H13 | 119.1 |
C4—C5—H5 | 121.1 | C13—C14—C15 | 121.7 (3) |
C6—C5—H5 | 121.1 | C13—C14—H14 | 119.2 |
O1—C6—C1 | 121.8 (2) | C15—C14—H14 | 119.2 |
O1—C6—C5 | 115.7 (2) | C16—C15—C14 | 117.5 (3) |
C1—C6—C5 | 122.5 (2) | C16—C15—H15 | 121.3 |
C8—C7—O1 | 124.8 (2) | C14—C15—H15 | 121.3 |
C8—C7—H7 | 117.6 | C15—C16—C11 | 120.1 (2) |
O1—C7—H7 | 117.6 | C15—C16—N1 | 131.0 (2) |
C7—C8—C9 | 121.3 (2) | C11—C16—N1 | 108.8 (2) |
C10—S1—C8—C7 | −102.78 (19) | C2—C1—C9—C8 | 178.82 (18) |
C10—S1—C8—C9 | 79.95 (19) | C1—C2—C3—C4 | −0.5 (4) |
C8—S1—C10—N1 | 2.5 (2) | C5—C4—C3—C2 | 0.1 (4) |
C8—S1—C10—O3 | −177.82 (15) | C3—C4—C5—C6 | 0.0 (4) |
C7—O1—C6—C1 | 0.3 (3) | O1—C6—C5—C4 | 179.1 (2) |
C7—O1—C6—C5 | −178.55 (18) | C1—C6—C5—C4 | 0.3 (3) |
C6—O1—C7—C8 | −1.0 (3) | C9—C8—C7—O1 | 0.3 (4) |
C11—O3—C10—N1 | −0.5 (2) | S1—C8—C7—O1 | −176.91 (16) |
C11—O3—C10—S1 | 179.82 (14) | C7—C8—C9—O2 | −178.5 (2) |
C10—O3—C11—C12 | −177.9 (2) | S1—C8—C9—O2 | −1.3 (3) |
C10—O3—C11—C16 | 0.5 (2) | C7—C8—C9—C1 | 1.0 (3) |
C16—N1—C10—O3 | 0.3 (3) | S1—C8—C9—C1 | 178.19 (14) |
C16—N1—C10—S1 | 179.92 (17) | C16—C11—C12—C13 | 1.3 (3) |
C10—N1—C16—C15 | 179.4 (3) | O3—C11—C12—C13 | 179.4 (2) |
C10—N1—C16—C11 | 0.1 (2) | C14—C13—C12—C11 | 0.0 (4) |
C6—C1—C2—C3 | 0.7 (3) | C12—C13—C14—C15 | −1.4 (4) |
C9—C1—C2—C3 | −179.8 (2) | C13—C14—C15—C16 | 1.4 (4) |
C2—C1—C6—O1 | −179.36 (18) | C15—C16—C11—C12 | −1.3 (4) |
C9—C1—C6—O1 | 1.1 (3) | N1—C16—C11—C12 | 178.1 (2) |
C2—C1—C6—C5 | −0.6 (3) | C15—C16—C11—O3 | −179.7 (2) |
C9—C1—C6—C5 | 179.86 (19) | N1—C16—C11—O3 | −0.3 (2) |
C6—C1—C9—O2 | 177.8 (2) | C11—C16—C15—C14 | −0.1 (4) |
C2—C1—C9—O2 | −1.7 (3) | N1—C16—C15—C14 | −179.4 (2) |
C6—C1—C9—C8 | −1.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O2i | 0.93 | 2.51 | 3.231 (3) | 135 |
Symmetry code: (i) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C16H9NO3S |
Mr | 295.30 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 291 |
a, b, c (Å) | 13.3357 (10), 6.7749 (5), 15.0185 (11) |
β (°) | 107.417 (1) |
V (Å3) | 1294.68 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.20 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART 4K CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9560, 2939, 2128 |
Rint | 0.118 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.159, 0.99 |
No. of reflections | 2939 |
No. of parameters | 190 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.45, −0.35 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Bruker, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O2i | 0.93 | 2.51 | 3.231 (3) | 134.8 |
Symmetry code: (i) x, y−1, z. |
Flavonoids, occurring widely throughout the plant kingdom, are one of the most representative families of plant secondary metabolites and display a remarkable spectrum of biological activities. They are one of the most important groups of biological compounds in nature, and are used as a synthetic lead for drug discovery (Ren et al., 2003; Kim et al., 2004). The title compound, (I), is a flavonoid derivative with bioactive heterocyclic thioether subunit. We herein report its crystal structure.
In the molecule of the title compound, (I), (Fig. 1), the bond lengths and angles are generally within normal ranges (Allen et al., 1987).
The rings A (C1—C6), B (O1/C1/C6—C9), C (N1/O3/C10/C11/C16) and D (C11—C16) are, of course, planar and the dihedral angles between them are A/B = 1.0 (1)° and C/D = 1.0 (1)°. So, the rings A, B and C, D are coplanar and they are also oriented at a dihedral angle of 78.0 (1)°.
In the crystal structure, the intermolecular C—H···O hydrogen bonds link the molecules into chains along the b axis (Fig. 2), in which they may be effective in the stabilization of the structure. Further stability is provided by the offset π-π stacking interactions (Janiak, 2000) involving the adjacent coplanar rings C and D with centroid···centroid (symmetry code: 1 - x, 1 - y, 1 - z) distance of 3.89 (1) Å, beside of the adjacent D rings with centroid···centroid (symmetry code: 1 - x, -y, 1 - z) distance of 3.93 (1) Å.