Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page m1442
https://doi.org/10.1107/S160053680904358X

Bis(2-amino-4-chloro­benzoato)tri­phenyl­anti­mony(V)

Liyuan Wen,a Handong Yina* and Chuanhua Wanga

aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
*Correspondence e-mail: handongyin@163.com

(Received 10 October 2009; accepted 22 October 2009; online 28 October 2009)

The title complex mol­ecule, [Sb(C6H5)3(C7H5ClNO2)2], possesses crystallographically imposed C2 symmetry. The Sb atom exhibits a trigonal-bipyramidal geometry with the axial positions occupied by the O atoms of two carboxyl­ate groups and the equatorial positions by the C atoms of the phenyl groups. Intra­molecular N—H⋯O and C—H⋯O hydrogen bonds occur.

Related literature

For related structures, see: Yin et al. (2009[Yin, H. D., Wen, L. Y., Cui, J. C. & Li, W. K. (2009). Polyhedron, 28, 2919-2926.]); Ferguson et al. (1987[Ferguson, G., Glidewell, C., Kaitner, B., Lloyd, D. & Metcalfe, S. (1987). Acta Cryst. C43, 824-826.]); Rüther et al. (1985[Rüther, R., Huber, F. & Preut, H. (1985). J. Organomet. Chem. 295, 21-28.]).

[Scheme 1]

Experimental

Crystal data

  • [Sb(C6H5)3(C7H5ClNO2)2]

  • Mr = 694.20

  • Orthorhombic, F d d 2

  • a = 13.0168 (13) Å

  • b = 20.298 (2) Å

  • c = 21.849 (3) Å

  • V = 5772.8 (11) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 1.18 mm−1

  • T = 298 K

  • 0.39 × 0.38 × 0.37 mm
Data collection

  • Siemens SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.656, Tmax = 0.669

  • 5819 measured reflections

  • 2493 independent reflections

  • 2222 reflections with I > 2σ(I)

  • Rint = 0.019
Refinement

  • R[F2 > 2σ(F2)] = 0.021

  • wR(F2) = 0.051

  • S = 1.11

  • 2493 reflections

  • 187 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.25 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1181 Friedel pairs

  • Flack parameter: −0.02 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O2 0.86 2.07 2.704 (5) 130
C15—H15⋯O1 0.93 2.33 2.905 (4) 119

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053680904358X/rz2373sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680904358X/rz2373Isup2.hkl

checkCIF report


Comment top

Organoantimony(V) complexes have been intensively studied owing to their versatile bonding modes (Yin et al., 2009) and biological applications. We have therefore synthesized the title compound, and present its crystal structure here.

The molecular structure of the compound is shown in Fig.1. The complex molecule possesses crystallographically imposed C2 symmetry, the rotation axis passing through the Sb atom and bisecting the C14–C17/C15'/C16' phenyl ring. The coordination geometry around the five-coordinate antimony atom can be described as slightly distorted trigonal bipyramidal, with three C atoms of the phenyl groups occupying the equatorial positions and two O atoms of carboxylate groups at the axial positions. The average Sb—O bond length of 2.122 (2) Å is approximately equal to the sum of the covalent radii of Sb and O (2.07 Å), and lies within the range from 1.935 Å observed in triphenylstibine oxide (Ferguson et al., 1987) to 2.506 Å found in tetraphenylstibonium benzenesulphonate hydrate (Rüther et al., 1985). The Sb—C bond distances (Sb1—C8 = 2.101 (3) Å; Sb1—C8A = 2.101 (3) Å; Sb1—C14 = 2.122 (4) Å) fall in the normal range for Sb—C(phenyl) bonds (2.10–2.13 Å). The conformation of the complex molecule is enforced by intramolecular N—H···O and C—H···O hydrogen bonds (Table 1). The crystal packing (Fig. 2) is stabilized only by van der Waals interactions.

Related literature top

For the related structures, see: Yin et al. (2009); Ferguson et al. (1987); Rüther et al. (1985).

Experimental top

The reaction was carried out under nitrogen atmosphere. 2-amino-4-chlorobenzoic acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to a stirred solution of methanol (30 ml) in a Schlenk flask and stirred for 0.5 h. Triphenylantimony dichloride (0.5 mmol) was then added to the reactor and the reaction mixture was stirred for 12 h at room temperature. The resulting clear solution was evaporated under vacuum. Colourless crystals suitable for X-ray analysis were obtained by slow evaporation of a ether/n-hexane (1:1 v/v) solution (yield 87%). Anal. Calcd (%) for C32H25Cl2N2O4Sb (Mr = 694.19): C, 55.37; H, 3.63; Cl, 10.21; N, 4.04. Found (%): C, 55.30; H, 3.74; Cl, 10.33; N, 4.16.

Refinement top

The C—H and N—H H atoms were positioned with idealized geometry and were refined isotropically using a riding model with N—H = 0.86 Å and C—H = 0.93 Å and with Uiso(H) = 1.2 Ueq(C, N).

Structure description top

Organoantimony(V) complexes have been intensively studied owing to their versatile bonding modes (Yin et al., 2009) and biological applications. We have therefore synthesized the title compound, and present its crystal structure here.

The molecular structure of the compound is shown in Fig.1. The complex molecule possesses crystallographically imposed C2 symmetry, the rotation axis passing through the Sb atom and bisecting the C14–C17/C15'/C16' phenyl ring. The coordination geometry around the five-coordinate antimony atom can be described as slightly distorted trigonal bipyramidal, with three C atoms of the phenyl groups occupying the equatorial positions and two O atoms of carboxylate groups at the axial positions. The average Sb—O bond length of 2.122 (2) Å is approximately equal to the sum of the covalent radii of Sb and O (2.07 Å), and lies within the range from 1.935 Å observed in triphenylstibine oxide (Ferguson et al., 1987) to 2.506 Å found in tetraphenylstibonium benzenesulphonate hydrate (Rüther et al., 1985). The Sb—C bond distances (Sb1—C8 = 2.101 (3) Å; Sb1—C8A = 2.101 (3) Å; Sb1—C14 = 2.122 (4) Å) fall in the normal range for Sb—C(phenyl) bonds (2.10–2.13 Å). The conformation of the complex molecule is enforced by intramolecular N—H···O and C—H···O hydrogen bonds (Table 1). The crystal packing (Fig. 2) is stabilized only by van der Waals interactions.

For the related structures, see: Yin et al. (2009); Ferguson et al. (1987); Rüther et al. (1985).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids. H atoms are omitted for clarity. Symmetry code: (A) = -x, -y, z.
[Figure 2] Fig. 2. The crystal packing of the title compound.
Bis(2-amino-4-chlorobenzoato)triphenylantimony(V) top
Crystal data top
[Sb(C6H5)3(C7H5ClNO2)2]F(000) = 2784
Mr = 694.20Dx = 1.597 Mg m−3
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 3849 reflections
a = 13.0168 (13) Åθ = 2.7–26.8°
b = 20.298 (2) ŵ = 1.18 mm−1
c = 21.849 (3) ÅT = 298 K
V = 5772.8 (11) Å3Block, colourless
Z = 80.39 × 0.38 × 0.37 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer		2493 independent reflections
Radiation source: fine-focus sealed tube2222 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −15→11
Tmin = 0.656, Tmax = 0.669k = −24→22
5819 measured reflectionsl = −25→24
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)] = 0.021H-atom parameters constrained
wR(F2) = 0.051 w = 1/[σ2(Fo2) + (0.0236P)2 + 0.2508P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
2493 reflectionsΔρmax = 0.35 e Å−3
187 parametersΔρmin = −0.25 e Å−3
1 restraintAbsolute structure: Flack (1983), 1181 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: −0.02 (2)
Crystal data top
[Sb(C6H5)3(C7H5ClNO2)2]V = 5772.8 (11) Å3
Mr = 694.20Z = 8
Orthorhombic, Fdd2Mo Kα radiation
a = 13.0168 (13) ŵ = 1.18 mm−1
b = 20.298 (2) ÅT = 298 K
c = 21.849 (3) Å0.39 × 0.38 × 0.37 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer		2493 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2222 reflections with I > 2σ(I)
Tmin = 0.656, Tmax = 0.669Rint = 0.019
5819 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.021H-atom parameters constrained
wR(F2) = 0.051Δρmax = 0.35 e Å−3
S = 1.11Δρmin = −0.25 e Å−3
2493 reflectionsAbsolute structure: Flack (1983), 1181 Friedel pairs
187 parametersAbsolute structure parameter: −0.02 (2)
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sb10.00000.00000.024065 (19)0.03974 (9)
Cl10.64382 (7)0.11557 (6)0.05169 (7)0.0943 (4)
N10.3358 (3)0.0520 (3)0.17751 (19)0.0964 (16)
H1A0.27330.03950.18280.116*
H1B0.37620.05590.20840.116*
O10.15241 (14)0.03663 (11)0.01894 (11)0.0483 (5)
O20.15456 (18)0.03090 (13)0.12027 (11)0.0561 (6)
C10.1992 (2)0.04151 (16)0.07150 (17)0.0450 (8)
C20.3091 (2)0.06030 (15)0.06822 (16)0.0448 (8)
C30.3705 (3)0.06552 (19)0.12053 (19)0.0576 (9)
C40.4750 (3)0.0831 (2)0.1132 (2)0.0675 (12)
H40.51730.08620.14740.081*
C50.5136 (3)0.0953 (2)0.0574 (3)0.0626 (13)
C60.4552 (4)0.0923 (2)0.0053 (2)0.0665 (14)
H60.48270.1026−0.03290.080*
C70.3533 (3)0.0734 (2)0.01176 (19)0.0613 (10)
H70.31300.0693−0.02320.074*
C8−0.0531 (2)0.09057 (16)0.05826 (17)0.0436 (8)
C9−0.0934 (2)0.13384 (17)0.01584 (19)0.0552 (9)
H9−0.09850.1214−0.02500.066*
C10−0.1264 (3)0.19567 (18)0.0339 (2)0.0695 (11)
H10−0.15190.22510.00510.083*
C11−0.1215 (3)0.2135 (2)0.0937 (3)0.0705 (12)
H11−0.14430.25490.10580.085*
C12−0.0830 (3)0.1705 (2)0.1366 (2)0.0671 (13)
H12−0.07980.18320.17740.081*
C13−0.0492 (3)0.10877 (18)0.11947 (17)0.0549 (9)
H13−0.02410.07960.14870.066*
C140.00000.0000−0.07304 (19)0.0384 (10)
C150.0908 (2)0.0031 (2)−0.10502 (17)0.0586 (10)
H150.15270.0057−0.08390.070*
C160.0907 (3)0.0024 (2)−0.16793 (18)0.0699 (12)
H160.15250.0036−0.18930.084*
C170.00000.0000−0.1989 (2)0.0627 (15)
H170.00000.0000−0.24150.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sb10.03262 (12)0.04916 (15)0.03746 (14)0.00228 (16)0.0000.000
Cl10.0427 (5)0.0907 (8)0.1495 (13)−0.0156 (5)0.0057 (6)−0.0279 (9)
N10.059 (2)0.183 (5)0.048 (3)0.000 (3)−0.0108 (18)0.003 (3)
O10.0361 (10)0.0658 (13)0.0429 (13)−0.0046 (10)−0.0065 (11)−0.0040 (13)
O20.0472 (13)0.0755 (16)0.0455 (14)−0.0046 (12)0.0037 (11)0.0019 (13)
C10.0366 (16)0.049 (2)0.049 (2)0.0028 (14)−0.0051 (16)−0.0044 (17)
C20.0375 (17)0.0476 (19)0.049 (2)0.0028 (13)−0.0048 (15)−0.0028 (16)
C30.045 (2)0.072 (2)0.056 (2)0.0052 (17)−0.0088 (18)−0.008 (2)
C40.048 (2)0.072 (3)0.082 (3)0.0027 (18)−0.021 (2)−0.016 (2)
C50.044 (2)0.057 (2)0.087 (4)−0.0050 (16)0.005 (2)−0.015 (2)
C60.048 (3)0.085 (3)0.067 (3)−0.010 (2)0.010 (2)−0.008 (2)
C70.047 (2)0.075 (3)0.063 (3)−0.0070 (18)0.0008 (18)−0.009 (2)
C80.0297 (15)0.050 (2)0.051 (2)0.0031 (14)0.0057 (15)−0.0010 (17)
C90.0478 (18)0.058 (2)0.059 (2)0.0043 (15)−0.0086 (17)−0.0025 (19)
C100.056 (2)0.055 (2)0.098 (4)0.0121 (16)−0.006 (2)0.002 (3)
C110.052 (2)0.057 (3)0.103 (4)0.0004 (19)0.010 (2)−0.013 (3)
C120.061 (2)0.072 (3)0.067 (3)−0.005 (2)0.012 (2)−0.024 (3)
C130.053 (2)0.059 (2)0.053 (2)0.0042 (16)0.0027 (18)−0.0049 (19)
C140.038 (2)0.046 (2)0.031 (2)0.0020 (19)0.0000.000
C150.0319 (17)0.099 (3)0.045 (2)−0.0012 (18)−0.0007 (15)−0.009 (2)
C160.046 (2)0.119 (4)0.045 (2)0.004 (2)0.0090 (17)−0.003 (2)
C170.062 (3)0.095 (4)0.031 (3)0.013 (3)0.0000.000
Geometric parameters (Å, º) top
Sb1—C8i2.101 (3)C7—H70.9300
Sb1—C82.101 (3)C8—C91.381 (5)
Sb1—C142.122 (4)C8—C131.388 (5)
Sb1—O12.1217 (19)C9—C101.384 (5)
Sb1—O1i2.1217 (19)C9—H90.9300
Cl1—C51.749 (4)C10—C111.357 (6)
N1—C31.352 (5)C10—H100.9300
N1—H1A0.8600C11—C121.373 (6)
N1—H1B0.8600C11—H110.9300
O1—C11.304 (4)C12—C131.380 (5)
O2—C11.233 (4)C12—H120.9300
C1—C21.482 (4)C13—H130.9300
C2—C71.387 (5)C14—C15i1.374 (4)
C2—C31.399 (5)C14—C151.374 (4)
C3—C41.416 (5)C15—C161.375 (5)
C4—C51.341 (7)C15—H150.9300
C4—H40.9300C16—C171.362 (5)
C5—C61.372 (6)C16—H160.9300
C6—C71.389 (6)C17—C16i1.362 (5)
C6—H60.9300C17—H170.9300
C8i—Sb1—C8138.3 (2)C2—C7—H7118.6
C8i—Sb1—C14110.83 (10)C6—C7—H7118.6
C8—Sb1—C14110.83 (10)C9—C8—C13119.4 (3)
C8i—Sb1—O191.03 (10)C9—C8—Sb1116.3 (3)
C8—Sb1—O191.12 (10)C13—C8—Sb1124.3 (3)
C14—Sb1—O186.98 (6)C8—C9—C10120.2 (4)
C8i—Sb1—O1i91.12 (10)C8—C9—H9119.9
C8—Sb1—O1i91.03 (10)C10—C9—H9119.9
C14—Sb1—O1i86.98 (6)C11—C10—C9120.1 (4)
O1—Sb1—O1i173.95 (13)C11—C10—H10119.9
C3—N1—H1A120.0C9—C10—H10119.9
C3—N1—H1B120.0C10—C11—C12120.2 (4)
H1A—N1—H1B120.0C10—C11—H11119.9
C1—O1—Sb1114.6 (2)C12—C11—H11119.9
O2—C1—O1121.9 (3)C11—C12—C13120.6 (4)
O2—C1—C2122.8 (3)C11—C12—H12119.7
O1—C1—C2115.3 (3)C13—C12—H12119.7
C7—C2—C3118.4 (3)C12—C13—C8119.4 (4)
C7—C2—C1119.5 (3)C12—C13—H13120.3
C3—C2—C1122.1 (3)C8—C13—H13120.3
N1—C3—C2123.1 (3)C15i—C14—C15118.9 (4)
N1—C3—C4118.4 (4)C15i—C14—Sb1120.6 (2)
C2—C3—C4118.4 (4)C15—C14—Sb1120.6 (2)
C5—C4—C3120.6 (4)C14—C15—C16120.5 (3)
C5—C4—H4119.7C14—C15—H15119.8
C3—C4—H4119.7C16—C15—H15119.8
C4—C5—C6122.7 (4)C17—C16—C15119.9 (4)
C4—C5—Cl1118.1 (4)C17—C16—H16120.1
C6—C5—Cl1119.2 (4)C15—C16—H16120.1
C5—C6—C7117.2 (4)C16—C17—C16i120.4 (5)
C5—C6—H6121.4C16—C17—H17119.8
C7—C6—H6121.4C16i—C17—H17119.8
C2—C7—C6122.7 (4)
Symmetry code: (i) −x, −y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O20.862.072.704 (5)130
C15—H15···O10.932.332.905 (4)119

Experimental details

Crystal data
Chemical formula[Sb(C6H5)3(C7H5ClNO2)2]
Mr694.20
Crystal system, space groupOrthorhombic, Fdd2
Temperature (K)298
a, b, c (Å)13.0168 (13), 20.298 (2), 21.849 (3)
V (Å3)5772.8 (11)
Z8
Radiation typeMo Kα
µ (mm−1)1.18
Crystal size (mm)0.39 × 0.38 × 0.37
Data collection
DiffractometerSiemens SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.656, 0.669
No. of measured, independent and
observed [I > 2σ(I)] reflections		5819, 2493, 2222
Rint0.019
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.021, 0.051, 1.11
No. of reflections2493
No. of parameters187
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.35, −0.25
Absolute structureFlack (1983), 1181 Friedel pairs
Absolute structure parameter−0.02 (2)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O20.862.072.704 (5)130
C15—H15···O10.932.332.905 (4)119
 

Acknowledgements

We acknowledge the National Natural Science Foundation of China (20771053) and the Natural Science Foundation of Shandong Province (Y2008B48) for financial support.

References

First citationFerguson, G., Glidewell, C., Kaitner, B., Lloyd, D. & Metcalfe, S. (1987). Acta Cryst. C43, 824–826.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationRüther, R., Huber, F. & Preut, H. (1985). J. Organomet. Chem. 295, 21–28.  Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationYin, H. D., Wen, L. Y., Cui, J. C. & Li, W. K. (2009). Polyhedron, 28, 2919–2926.  Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page m1442
https://doi.org/10.1107/S160053680904358X
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS