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In the mol­ecule of the title compound, C16H9NO3S, the two fused ring systems are each planar and make a dihedral angle of 78.0 (1)° with each other. In the crystal structure, inter­molecular C—H...O hydrogen bonds link the mol­ecules into chains along the b axis and there are also π–π stacking inter­actions. The distance between the adjacent ring centroids of the benzoxazole system is 3.89 (1) Å (symmetry code linking the adjacent rings: 1 − x, 1 − y, 1 − z). A further interaction occurs between two adjacent six-membered benzoxazole benzene rings (symmetry code: 1 − x, −y, 1 − z), with a centroid -to-centroid distance of 3.93 (1) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023914/hk2248sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023914/hk2248Isup2.hkl
Contains datablock I

CCDC reference: 651493

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](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

Comment top

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.

Related literature top

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).

Experimental top

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.

Refinement top

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).

Structure description top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A packing diagram for (I). H bonds are shown as dashed lines.
3-(1,3-Benzoxazol-2-ylsulfanyl)-4H-chromen-4-one top
Crystal data top
C16H9NO3SF(000) = 608
Mr = 295.30Dx = 1.515 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2673 reflections
a = 13.3357 (10) Åθ = 2.8–25.4°
b = 6.7749 (5) ŵ = 0.26 mm1
c = 15.0185 (11) ÅT = 291 K
β = 107.417 (1)°Plate, yellow
V = 1294.68 (17) Å30.20 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
2128 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.118
Graphite monochromatorθmax = 27.5°, θmin = 1.6°
φ and ω scansh = 1714
9560 measured reflectionsk = 88
2939 independent reflectionsl = 1917
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-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 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C16H9NO3SV = 1294.68 (17) Å3
Mr = 295.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.3357 (10) ŵ = 0.26 mm1
b = 6.7749 (5) ÅT = 291 K
c = 15.0185 (11) Å0.20 × 0.20 × 0.10 mm
β = 107.417 (1)°
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
2128 reflections with I > 2σ(I)
9560 measured reflectionsRint = 0.118
2939 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.159H-atom parameters constrained
S = 0.99Δρmax = 0.45 e Å3
2939 reflectionsΔρmin = 0.35 e Å3
190 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
S10.25607 (5)0.15017 (9)0.31455 (4)0.0564 (2)
O10.00612 (12)0.0770 (2)0.36603 (10)0.0529 (4)
O20.11610 (13)0.4808 (2)0.35113 (11)0.0617 (5)
O30.44360 (12)0.2234 (2)0.42736 (11)0.0546 (4)
N10.32159 (15)0.2063 (3)0.50334 (13)0.0501 (5)
C10.01555 (17)0.2751 (3)0.37804 (13)0.0429 (5)
C20.07754 (18)0.4293 (4)0.39490 (15)0.0529 (6)
H20.05640.55960.39280.064*
C30.1697 (2)0.3877 (4)0.41463 (17)0.0632 (7)
H30.21070.48990.42630.076*
C40.2016 (2)0.1924 (4)0.41714 (17)0.0645 (7)
H40.26410.16630.43040.077*
C50.14377 (18)0.0390 (4)0.40063 (16)0.0558 (6)
H50.16570.09090.40250.067*
C60.05054 (18)0.0830 (3)0.38089 (14)0.0463 (5)
C70.09752 (18)0.0436 (3)0.34882 (14)0.0490 (5)
H70.13570.15270.33990.059*
C80.13791 (17)0.1350 (3)0.34352 (15)0.0447 (5)
C90.08359 (18)0.3143 (3)0.35709 (14)0.0444 (5)
C100.34169 (17)0.1960 (3)0.42519 (16)0.0487 (6)
C110.49506 (18)0.2573 (3)0.52130 (17)0.0509 (6)
C120.5994 (2)0.3002 (4)0.5648 (2)0.0646 (7)
H120.64830.30960.53190.078*
C130.6269 (2)0.3284 (4)0.6604 (2)0.0710 (8)
H130.69630.35770.69290.085*
C140.5543 (2)0.3142 (4)0.7084 (2)0.0735 (8)
H140.57620.33130.77280.088*
C150.4496 (2)0.2751 (4)0.66347 (19)0.0678 (7)
H150.40050.26840.69620.081*
C160.42064 (18)0.2463 (3)0.56834 (16)0.0496 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0623 (4)0.0622 (4)0.0489 (4)0.0040 (3)0.0232 (3)0.0020 (3)
O10.0595 (10)0.0400 (8)0.0574 (10)0.0033 (7)0.0149 (8)0.0003 (7)
O20.0705 (12)0.0417 (9)0.0777 (12)0.0042 (8)0.0298 (9)0.0009 (8)
O30.0522 (10)0.0552 (9)0.0646 (11)0.0072 (7)0.0298 (8)0.0047 (8)
N10.0469 (11)0.0583 (11)0.0484 (11)0.0007 (9)0.0194 (9)0.0017 (9)
C10.0502 (13)0.0444 (11)0.0315 (11)0.0013 (9)0.0081 (9)0.0007 (8)
C20.0617 (15)0.0492 (12)0.0482 (13)0.0050 (11)0.0170 (11)0.0012 (10)
C30.0627 (17)0.0728 (17)0.0538 (15)0.0159 (14)0.0169 (12)0.0026 (12)
C40.0550 (15)0.088 (2)0.0516 (15)0.0049 (14)0.0172 (12)0.0011 (13)
C50.0549 (15)0.0601 (15)0.0506 (13)0.0097 (11)0.0130 (11)0.0018 (11)
C60.0542 (13)0.0460 (11)0.0330 (11)0.0025 (10)0.0044 (9)0.0001 (9)
C70.0578 (14)0.0416 (12)0.0444 (12)0.0044 (10)0.0105 (10)0.0010 (9)
C80.0512 (13)0.0432 (11)0.0375 (11)0.0009 (9)0.0099 (9)0.0014 (8)
C90.0549 (13)0.0406 (11)0.0349 (11)0.0007 (9)0.0094 (9)0.0022 (8)
C100.0489 (14)0.0415 (11)0.0592 (15)0.0062 (9)0.0215 (11)0.0046 (10)
C110.0477 (13)0.0412 (11)0.0655 (16)0.0082 (9)0.0197 (11)0.0070 (10)
C120.0466 (14)0.0549 (14)0.098 (2)0.0088 (11)0.0299 (14)0.0077 (14)
C130.0525 (16)0.0570 (15)0.092 (2)0.0069 (12)0.0039 (15)0.0015 (14)
C140.0648 (18)0.0763 (19)0.0681 (19)0.0070 (14)0.0030 (15)0.0031 (14)
C150.0619 (17)0.0843 (19)0.0571 (16)0.0021 (14)0.0176 (13)0.0028 (13)
C160.0475 (13)0.0504 (13)0.0542 (14)0.0050 (10)0.0203 (11)0.0048 (10)
Geometric parameters (Å, º) top
S1—C101.739 (2)C4—C51.361 (4)
S1—C81.759 (2)C6—C51.394 (3)
O1—C61.378 (3)C7—H70.9300
O1—C71.339 (3)C8—C71.337 (3)
O3—C101.362 (3)C8—C91.460 (3)
O3—C111.391 (3)C9—O21.221 (2)
N1—C101.282 (3)C11—C121.380 (4)
N1—C161.414 (3)C11—C121.380 (4)
C1—C21.401 (3)C12—H120.9300
C1—C61.387 (3)C13—C121.384 (4)
C1—C91.472 (3)C13—H130.9300
C2—C31.377 (3)C13—C141.373 (4)
C2—H20.9300C14—H140.9300
C5—H50.9300C14—C151.383 (4)
C3—H30.9300C15—H150.9300
C4—C31.394 (4)C16—C111.382 (3)
C4—H40.9300C16—C151.378 (3)
C10—S1—C898.90 (10)C7—C8—S1118.32 (17)
C7—O1—C6118.26 (16)C9—C8—S1120.31 (16)
C10—O3—C11103.44 (16)O2—C9—C8123.8 (2)
C10—N1—C16103.55 (18)O2—C9—C1122.9 (2)
C6—C1—C2118.1 (2)C8—C9—C1113.23 (18)
C6—C1—C9120.54 (19)N1—C10—O3116.8 (2)
C2—C1—C9121.3 (2)N1—C10—S1128.83 (18)
C3—C2—C1120.0 (2)O3—C10—S1114.33 (16)
C3—C2—H2120.0C12—C11—C16123.1 (2)
C1—C2—H2120.0C12—C11—O3129.5 (2)
C2—C3—C4120.0 (2)C16—C11—O3107.3 (2)
C2—C3—H3120.0C11—C12—C13115.9 (2)
C4—C3—H3120.0C11—C12—H12122.1
C5—C4—C3121.7 (2)C13—C12—H12122.1
C5—C4—H4119.1C14—C13—C12121.7 (3)
C3—C4—H4119.1C14—C13—H13119.1
C4—C5—C6117.8 (2)C12—C13—H13119.1
C4—C5—H5121.1C13—C14—C15121.7 (3)
C6—C5—H5121.1C13—C14—H14119.2
O1—C6—C1121.8 (2)C15—C14—H14119.2
O1—C6—C5115.7 (2)C16—C15—C14117.5 (3)
C1—C6—C5122.5 (2)C16—C15—H15121.3
C8—C7—O1124.8 (2)C14—C15—H15121.3
C8—C7—H7117.6C15—C16—C11120.1 (2)
O1—C7—H7117.6C15—C16—N1131.0 (2)
C7—C8—C9121.3 (2)C11—C16—N1108.8 (2)
C10—S1—C8—C7102.78 (19)C2—C1—C9—C8178.82 (18)
C10—S1—C8—C979.95 (19)C1—C2—C3—C40.5 (4)
C8—S1—C10—N12.5 (2)C5—C4—C3—C20.1 (4)
C8—S1—C10—O3177.82 (15)C3—C4—C5—C60.0 (4)
C7—O1—C6—C10.3 (3)O1—C6—C5—C4179.1 (2)
C7—O1—C6—C5178.55 (18)C1—C6—C5—C40.3 (3)
C6—O1—C7—C81.0 (3)C9—C8—C7—O10.3 (4)
C11—O3—C10—N10.5 (2)S1—C8—C7—O1176.91 (16)
C11—O3—C10—S1179.82 (14)C7—C8—C9—O2178.5 (2)
C10—O3—C11—C12177.9 (2)S1—C8—C9—O21.3 (3)
C10—O3—C11—C160.5 (2)C7—C8—C9—C11.0 (3)
C16—N1—C10—O30.3 (3)S1—C8—C9—C1178.19 (14)
C16—N1—C10—S1179.92 (17)C16—C11—C12—C131.3 (3)
C10—N1—C16—C15179.4 (3)O3—C11—C12—C13179.4 (2)
C10—N1—C16—C110.1 (2)C14—C13—C12—C110.0 (4)
C6—C1—C2—C30.7 (3)C12—C13—C14—C151.4 (4)
C9—C1—C2—C3179.8 (2)C13—C14—C15—C161.4 (4)
C2—C1—C6—O1179.36 (18)C15—C16—C11—C121.3 (4)
C9—C1—C6—O11.1 (3)N1—C16—C11—C12178.1 (2)
C2—C1—C6—C50.6 (3)C15—C16—C11—O3179.7 (2)
C9—C1—C6—C5179.86 (19)N1—C16—C11—O30.3 (2)
C6—C1—C9—O2177.8 (2)C11—C16—C15—C140.1 (4)
C2—C1—C9—O21.7 (3)N1—C16—C15—C14179.4 (2)
C6—C1—C9—C81.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O2i0.932.513.231 (3)135
Symmetry code: (i) x, y1, z.

Experimental details

Crystal data
Chemical formulaC16H9NO3S
Mr295.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)291
a, b, c (Å)13.3357 (10), 6.7749 (5), 15.0185 (11)
β (°) 107.417 (1)
V3)1294.68 (17)
Z4
Radiation typeMo Kα
µ (mm1)0.26
Crystal size (mm)0.20 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART 4K CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
9560, 2939, 2128
Rint0.118
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.159, 0.99
No. of reflections2939
No. of parameters190
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O2i0.932.513.231 (3)134.8
Symmetry code: (i) x, y1, z.
 

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