Bis[2-(1,3-benzo-thia-zol-2-yl)phenyl-κ(2) C (1),N][1,3-bis-(4-bromo-phen-yl)propane-1,3-dionato-κ(2) O,O']iridium(III).

The title complex, [Ir(C15H9Br2O2)(C13H8NS)2], lies about a crystallographic twofold rotation axis passing through the Ir(III) atom and the central C atom of the bis-(bromo-phen-yl)propane-1,3-dionate ligand. The Ir(III) atom adopts a distorted octa-hedral geometry coordinated by two N atoms in the axial positions, and two C and two O atoms in the equatorial plane. The dihedral angle between the two thia-zole ring systems in the complex is 77.45 (10)°.

Related literature

For luminescent Ir complexes, see: Ulbricht et al. (2009 ▶); Liu et al. (2008 ▶); Hwang et al. (2005 ▶); Tsuboyama et al. (2003 ▶); Bera et al. (2007 ▶). For phospho­rescent Ir complexes, see: Xu et al. (2009 ▶); Sengottuvelan et al. (2011 ▶, 2013 ▶).

Experimental

Crystal data

[Ir(C15H9Br2O2)(C13H8NS)2]

M = 993.77

Monoclinic,

a = 15.888 (4) Å

b = 12.689 (3) Å

c = 17.143 (5) Å

β = 100.28 (5)°

V = 3400.8 (16) Å3

Z = 4

Mo Kα radiation

μ = 6.44 mm−1

T = 203 K

0.35 × 0.29 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.132, T max = 0.365

15842 measured reflections

4079 independent reflections

3623 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.076

S = 1.06

4079 reflections

227 parameters

H-atom parameters constrained

Δρmax = 1.55 e Å−3

Δρmin = −1.26 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2013 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813018394/is5287sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018394/is5287Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ir(C15H9Br2O2)(C13H8NS)2]	F(000) = 1920
Mr = 993.77	Dx = 1.941 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6529 reflections
a = 15.888 (4) Å	θ = 2.3–28.2°
b = 12.689 (3) Å	µ = 6.44 mm−1
c = 17.143 (5) Å	T = 203 K
β = 100.28 (5)°	Block, red
V = 3400.8 (16) Å3	0.35 × 0.29 × 0.16 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3623 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
φ and ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→21
Tmin = 0.132, Tmax = 0.365	k = −16→8
15842 measured reflections	l = −21→21
4079 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030	H-atom parameters constrained
wR(F2) = 0.076	w = 1/[σ2(Fo2) + (0.0363P)2 + 6.8133P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
4079 reflections	Δρmax = 1.55 e Å−3
227 parameters	Δρmin = −1.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
Ir1	0	0.38790 (2)	0.25	0.01610 (7)
O2	0.02867 (16)	0.2664 (2)	0.33857 (15)	0.0201 (5)
C3	0.0262 (2)	0.1685 (3)	0.3239 (2)	0.0198 (7)
C4	0	0.1208 (4)	0.25	0.0307 (13)
H4	0	0.0475	0.25	0.037*
C5	0.0587 (2)	0.0971 (3)	0.3927 (2)	0.0206 (7)
C6	0.1155 (3)	0.1359 (3)	0.4576 (2)	0.0270 (8)
H6	0.1298	0.207	0.4595	0.032*
C7	0.1512 (3)	0.0701 (4)	0.5198 (3)	0.0311 (9)
H7	0.1909	0.0961	0.562	0.037*
C8	0.1264 (3)	−0.0348 (3)	0.5177 (3)	0.0290 (9)
C9	0.0688 (3)	−0.0745 (3)	0.4554 (2)	0.0265 (8)
H9	0.0528	−0.145	0.4547	0.032*
C10	0.0349 (3)	−0.0081 (3)	0.3935 (2)	0.0244 (8)
H10	−0.0047	−0.0346	0.3516	0.029*
Br11	0.17062 (3)	−0.12509 (4)	0.60339 (3)	0.04469 (14)
N12	0.11887 (19)	0.3940 (2)	0.21803 (19)	0.0202 (6)
C13	0.1968 (2)	0.3442 (3)	0.2459 (2)	0.0207 (7)
C14	0.2596 (2)	0.3667 (3)	0.1998 (2)	0.0244 (8)
S15	0.21858 (6)	0.45204 (9)	0.12315 (6)	0.0295 (2)
C16	0.1222 (2)	0.4541 (3)	0.1558 (2)	0.0199 (7)
C17	0.0476 (2)	0.5149 (3)	0.1241 (2)	0.0196 (7)
C18	−0.0208 (2)	0.4977 (3)	0.1654 (2)	0.0184 (7)
C19	−0.0952 (2)	0.5581 (3)	0.1394 (2)	0.0261 (8)
H19	−0.1418	0.5513	0.165	0.031*
C20	−0.0997 (3)	0.6271 (3)	0.0762 (3)	0.0303 (9)
H20	−0.1496	0.6655	0.0603	0.036*
C21	−0.0318 (3)	0.6408 (3)	0.0359 (2)	0.0268 (9)
H21	−0.0362	0.6875	−0.0064	0.032*
C22	0.0422 (2)	0.5837 (3)	0.0601 (2)	0.0228 (8)
H22	0.0883	0.5911	0.0337	0.027*
C23	0.2167 (2)	0.2787 (3)	0.3110 (2)	0.0268 (8)
H23	0.1763	0.2638	0.3425	0.032*
C24	0.2977 (3)	0.2359 (4)	0.3284 (3)	0.0333 (10)
H24	0.3115	0.1915	0.372	0.04*
C25	0.3590 (3)	0.2575 (4)	0.2825 (3)	0.0329 (10)
H25	0.413	0.2272	0.2954	0.039*
C26	0.3408 (3)	0.3236 (4)	0.2180 (3)	0.0327 (9)
H26	0.382	0.3388	0.1873	0.039*

	U11	U22	U33	U12	U13	U23
Ir1	0.01424 (10)	0.01535 (10)	0.01891 (12)	0	0.00346 (7)	0
O2	0.0234 (13)	0.0187 (13)	0.0190 (13)	−0.0013 (10)	0.0061 (10)	0.0028 (9)
C3	0.0209 (16)	0.0198 (18)	0.0201 (19)	−0.0006 (14)	0.0074 (14)	0.0040 (13)
C4	0.051 (4)	0.017 (3)	0.025 (3)	0	0.011 (3)	0
C5	0.0246 (18)	0.0197 (18)	0.0198 (19)	0.0025 (14)	0.0105 (14)	−0.0005 (13)
C6	0.0275 (19)	0.026 (2)	0.028 (2)	−0.0048 (16)	0.0062 (16)	0.0025 (15)
C7	0.0256 (19)	0.038 (2)	0.029 (2)	−0.0043 (18)	0.0026 (17)	0.0056 (17)
C8	0.0233 (18)	0.032 (2)	0.034 (2)	0.0048 (17)	0.0113 (17)	0.0138 (17)
C9	0.035 (2)	0.0183 (17)	0.029 (2)	0.0041 (16)	0.0139 (17)	0.0062 (15)
C10	0.0297 (19)	0.0208 (18)	0.024 (2)	−0.0005 (15)	0.0071 (16)	0.0023 (14)
Br11	0.0279 (2)	0.0540 (3)	0.0503 (3)	0.0050 (2)	0.0020 (2)	0.0296 (2)
N12	0.0169 (14)	0.0209 (15)	0.0228 (16)	0.0005 (12)	0.0034 (12)	−0.0015 (12)
C13	0.0143 (15)	0.0221 (18)	0.025 (2)	−0.0021 (14)	0.0016 (14)	−0.0042 (14)
C14	0.0207 (18)	0.025 (2)	0.028 (2)	0.0032 (15)	0.0063 (15)	0.0046 (14)
S15	0.0228 (5)	0.0371 (6)	0.0312 (6)	0.0040 (4)	0.0114 (4)	0.0114 (4)
C16	0.0198 (17)	0.0213 (17)	0.0185 (18)	−0.0025 (14)	0.0035 (14)	−0.0005 (13)
C17	0.0200 (17)	0.0193 (17)	0.0182 (18)	0.0002 (14)	0.0001 (14)	−0.0018 (13)
C18	0.0192 (16)	0.0154 (16)	0.0195 (19)	0.0010 (13)	0.0008 (14)	−0.0028 (12)
C19	0.0221 (18)	0.025 (2)	0.030 (2)	0.0033 (15)	0.0022 (16)	0.0000 (15)
C20	0.030 (2)	0.027 (2)	0.032 (2)	0.0094 (17)	0.0010 (17)	0.0011 (16)
C21	0.038 (2)	0.0191 (18)	0.022 (2)	−0.0004 (16)	0.0017 (17)	0.0013 (14)
C22	0.0251 (18)	0.0228 (18)	0.0200 (19)	−0.0028 (15)	0.0026 (15)	−0.0013 (14)
C23	0.0187 (17)	0.029 (2)	0.033 (2)	0.0008 (15)	0.0062 (16)	0.0096 (16)
C24	0.028 (2)	0.036 (2)	0.035 (2)	0.0082 (18)	0.0020 (18)	0.0116 (18)
C25	0.0216 (19)	0.035 (2)	0.041 (3)	0.0119 (17)	0.0036 (18)	0.0038 (18)
C26	0.0225 (19)	0.038 (2)	0.041 (3)	0.0040 (18)	0.0143 (17)	0.0054 (19)

Ir1—C18i	1.996 (4)	C13—C23	1.382 (5)
Ir1—C18	1.996 (4)	C13—C14	1.407 (5)
Ir1—N12i	2.060 (3)	C14—C26	1.385 (5)
Ir1—N12	2.060 (3)	C14—S15	1.738 (4)
Ir1—O2i	2.155 (3)	S15—C16	1.722 (4)
Ir1—O2	2.155 (3)	C16—C17	1.436 (5)
O2—C3	1.266 (4)	C17—C22	1.394 (5)
C3—C4	1.399 (4)	C17—C18	1.415 (5)
C3—C5	1.505 (5)	C18—C19	1.413 (5)
C4—C3i	1.399 (4)	C19—C20	1.384 (6)
C4—H4	0.93	C19—H19	0.93
C5—C10	1.388 (5)	C20—C21	1.392 (6)
C5—C6	1.391 (6)	C20—H20	0.93
C6—C7	1.392 (6)	C21—C22	1.381 (6)
C6—H6	0.93	C21—H21	0.93
C7—C8	1.387 (6)	C22—H22	0.93
C7—H7	0.93	C23—C24	1.380 (5)
C8—C9	1.372 (6)	C23—H23	0.93
C8—Br11	1.896 (4)	C24—C25	1.384 (6)
C9—C10	1.386 (5)	C24—H24	0.93
C9—H9	0.93	C25—C26	1.377 (6)
C10—H10	0.93	C25—H25	0.93
N12—C16	1.320 (5)	C26—H26	0.93
N12—C13	1.396 (5)
C18i—Ir1—C18	91.4 (2)	C13—N12—Ir1	133.7 (3)
C18i—Ir1—N12i	79.67 (14)	C23—C13—N12	127.6 (3)
C18—Ir1—N12i	97.27 (14)	C23—C13—C14	119.5 (3)
C18i—Ir1—N12	97.27 (14)	N12—C13—C14	113.0 (3)
C18—Ir1—N12	79.67 (14)	C26—C14—C13	121.3 (4)
N12i—Ir1—N12	175.67 (17)	C26—C14—S15	128.7 (3)
C18i—Ir1—O2i	176.72 (12)	C13—C14—S15	110.1 (3)
C18—Ir1—O2i	90.04 (12)	C16—S15—C14	89.93 (18)
N12i—Ir1—O2i	97.24 (11)	N12—C16—C17	117.8 (3)
N12—Ir1—O2i	85.88 (11)	N12—C16—S15	114.8 (3)
C18i—Ir1—O2	90.04 (12)	C17—C16—S15	127.3 (3)
C18—Ir1—O2	176.72 (12)	C22—C17—C18	123.1 (3)
N12i—Ir1—O2	85.88 (11)	C22—C17—C16	124.4 (4)
N12—Ir1—O2	97.24 (11)	C18—C17—C16	112.5 (3)
O2i—Ir1—O2	88.63 (14)	C19—C18—C17	115.6 (3)
C3—O2—Ir1	124.5 (2)	C19—C18—Ir1	129.0 (3)
O2—C3—C4	126.8 (4)	C17—C18—Ir1	115.4 (3)
O2—C3—C5	116.2 (3)	C20—C19—C18	120.9 (4)
C4—C3—C5	117.0 (4)	C20—C19—H19	119.5
C3i—C4—C3	128.7 (5)	C18—C19—H19	119.5
C3i—C4—H4	115.7	C19—C20—C21	122.1 (4)
C3—C4—H4	115.7	C19—C20—H20	119
C10—C5—C6	118.1 (4)	C21—C20—H20	119
C10—C5—C3	122.1 (3)	C22—C21—C20	118.6 (4)
C6—C5—C3	119.8 (3)	C22—C21—H21	120.7
C5—C6—C7	121.2 (4)	C20—C21—H21	120.7
C5—C6—H6	119.4	C21—C22—C17	119.6 (4)
C7—C6—H6	119.4	C21—C22—H22	120.2
C8—C7—C6	118.7 (4)	C17—C22—H22	120.2
C8—C7—H7	120.7	C24—C23—C13	118.8 (4)
C6—C7—H7	120.7	C24—C23—H23	120.6
C9—C8—C7	121.3 (4)	C13—C23—H23	120.6
C9—C8—Br11	119.0 (3)	C23—C24—C25	121.5 (4)
C7—C8—Br11	119.7 (3)	C23—C24—H24	119.3
C8—C9—C10	119.1 (4)	C25—C24—H24	119.3
C8—C9—H9	120.4	C26—C25—C24	120.6 (4)
C10—C9—H9	120.4	C26—C25—H25	119.7
C9—C10—C5	121.5 (4)	C24—C25—H25	119.7
C9—C10—H10	119.2	C25—C26—C14	118.3 (4)
C5—C10—H10	119.2	C25—C26—H26	120.8
C16—N12—C13	112.2 (3)	C14—C26—H26	120.8
C16—N12—Ir1	114.0 (2)

Table 1

Selected bond lengths (Å)

Ir1—C18	1.996 (4)
Ir1—N12	2.060 (3)
Ir1—O2	2.155 (3)