fac-Bromidotricarbonyl[2-(diisopropylphosphanyl)benzaldehyde-κ(2)O,P]rhenium(I).

The structure of the title complex, [ReBr(C(13)H(19)OP)(CO)(3)], displays a facial coordination of the three CO ligands and a κ(2)O,P coordination mode of the 2-diisopropyl-phosphino-benzaldehyde ligands. The Re-C bond distance for the CO ligand trans to the P atom is, due to its trans influence, elongated to 1.943 (3) Å, showing that this CO ligand is more weakly bound to the Re centre than the other two.

Related literature

For the structures of halo-fac-tricarbonyl-[κ2 O,P-(ligand)]rhenium(I) complexes with ligands based on 2-diphenyl­phosphinobenzaldehyde or 2-diphenyl­phosphinobenzoic acid derivatives, see: Correia et al. (2001 ▶); Chen et al. (2001 ▶); Palma et al. (2004 ▶).

Experimental

Crystal data

[ReBr(C13H19OP)(CO)3]

M = 572.39

Monoclinic,

a = 10.750 (2) Å

b = 15.194 (3) Å

c = 13.699 (3) Å

β = 125.29 (3)°

V = 1826.4 (9) Å3

Z = 4

Mo Kα radiation

μ = 8.94 mm−1

T = 200 K

0.43 × 0.33 × 0.31 mm

Data collection

Siemens SMART 1000 CCD diffractometer

Absorption correction: numerical SADABS (Bruker, 1997 ▶) T min = 0.631, T max = 1

18487 measured reflections

4436 independent reflections

4095 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.018

wR(F 2) = 0.045

S = 1.11

4436 reflections

221 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.51 e Å−3

Δρmin = −1.04 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XPMA (Zsolnai, 1996 ▶), ORTEP (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812035957/vn2046sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035957/vn2046Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035957/vn2046Isup3.mol

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

[ReBr(C13H19OP)(CO)3]	F(000) = 1088
Mr = 572.39	Dx = 2.082 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 165 reflections
a = 10.750 (2) Å	θ = 2.3–28.3°
b = 15.194 (3) Å	µ = 8.94 mm−1
c = 13.699 (3) Å	T = 200 K
β = 125.29 (3)°	Cube, orange
V = 1826.4 (9) Å3	0.43 × 0.33 × 0.31 mm
Z = 4

Siemens SMART 1000 CCD diffractometer	4436 independent reflections
Radiation source: fine-focus sealed tube	4095 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 8 pixels mm-1	θmax = 28.3°, θmin = 2.3°
ω scans	h = −14→14
Absorption correction: numerical SADABS (Bruker, 1997)	k = −19→19
Tmin = 0.631, Tmax = 1	l = −17→17
18487 measured reflections

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)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.045	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.0228P)2 + 0.987P] where P = (Fo2 + 2Fc2)/3
4436 reflections	(Δ/σ)max = 0.002
221 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −1.04 e Å−3

Experimental. Spectroscopic data: 1H{31P} NMR (CDCl3): δ = 9.71, s, 1H, CHO; 7.99, dd, 3JHH = 7.5 Hz, 4JHH = 1.2 Hz, 1H, CH(arom); 7.89, dt, 3JHH = 7.5 Hz, 4JHH = 1.2 Hz, 1H, CH(arom); 7.78, dt, 3JHH = 7.5 Hz, 4JHH = 1.2 Hz, 1H, CH(arom); 7.72, dd, 3JHH = 7.5 Hz, 4JHH = 1.2 Hz, 1H, CH(arom); 2.94, hept, 3JHH = 7.0 Hz, 1H, CH(Me)2; 2.55, hept, 3JHH = 6.9 Hz, 1H, CH(Me)2; 1.38, d, 3JHH = 7.0 Hz, 3H, CH3; 1.31, d, 3JHH = 7.0 Hz, 3H, CH3; 1.03, d, 3JHH = 7.0 Hz, 3H, CH3; 0.97, d, 3JHH = 6.9 Hz, 3H, CH3; 31P{1H} NMR (CDCl3): δ = 19.7, s; 13C{31P}{1H} NMR (CDCl3): δ = 200.6; 196.2; 190.3; 141.0; 136.0; 132.5; 131.6; 27.9; 23.3; 18.9; 18.2; 17.2; 16.2; IR νCO [cm-1]: 2041, 1949, 1905, 1634; UV vis (CHCl3): 414 nm (ε 2142); 261 nm (ε 9780); UV vis (MeCN): 391 nm (ε 1794); 312 nm (sh); 257 nm (ε 7952); 214 nm (ε 27000)

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. The data of the structure have been deposited at the CCDC with the reference number 894003 (Allen, 2002).

	x	y	z	Uiso*/Ueq
Re1	0.096757 (10)	0.651316 (6)	0.822326 (9)	0.01984 (4)
Br1	0.09257 (4)	0.70831 (2)	1.00026 (3)	0.03331 (7)
P1	−0.17759 (7)	0.68270 (4)	0.68063 (6)	0.01901 (13)
O1	0.0136 (2)	0.53062 (12)	0.85118 (17)	0.0246 (4)
O2	0.2119 (2)	0.83034 (14)	0.8052 (2)	0.0381 (5)
O3	0.4316 (2)	0.59455 (16)	1.0029 (2)	0.0446 (6)
O4	0.1170 (3)	0.57547 (15)	0.6249 (2)	0.0387 (5)
C1	−0.2889 (3)	0.63407 (17)	0.7300 (2)	0.0217 (5)
C2	−0.4274 (3)	0.6705 (2)	0.6956 (3)	0.0294 (6)
H2	−0.4596	0.7228	0.6525	0.035 (4)*
C3	−0.5192 (3)	0.6307 (2)	0.7243 (3)	0.0343 (7)
H3	−0.6104	0.6571	0.7013	0.035 (4)*
C4	−0.4759 (3)	0.5528 (2)	0.7861 (3)	0.0320 (6)
H4	−0.5383	0.5258	0.8038	0.035 (4)*
C5	−0.3387 (3)	0.51476 (19)	0.8221 (2)	0.0275 (6)
H5	−0.3092	0.4618	0.8638	0.035 (4)*
C6	−0.2436 (3)	0.55548 (17)	0.7962 (2)	0.0220 (5)
C7	−0.1008 (3)	0.50735 (17)	0.8444 (2)	0.0231 (5)
C8	−0.2409 (3)	0.79816 (17)	0.6455 (3)	0.0273 (6)
H8	−0.3526	0.7981	0.5939	0.038 (9)*
C9	−0.1909 (4)	0.8520 (2)	0.7555 (3)	0.0427 (8)
H9A	−0.0820	0.8576	0.8046	0.049 (4)*
H9B	−0.2227	0.8231	0.8000	0.049 (4)*
H9C	−0.2365	0.9093	0.7316	0.049 (4)*
C10	−0.1865 (4)	0.8395 (2)	0.5746 (3)	0.0390 (8)
H10A	−0.2189	0.8998	0.5572	0.049 (4)*
H10B	−0.2292	0.8077	0.5011	0.049 (4)*
H10C	−0.0773	0.8368	0.6209	0.049 (4)*
C11	−0.2622 (3)	0.6290 (2)	0.5325 (3)	0.0288 (6)
H11	−0.2026	0.6485	0.5029	0.030 (9)*
C12	−0.4282 (4)	0.6553 (2)	0.4382 (3)	0.0429 (8)
H12A	−0.4655	0.6244	0.3650	0.048 (4)*
H12B	−0.4338	0.7176	0.4242	0.048 (4)*
H12C	−0.4892	0.6404	0.4663	0.048 (4)*
C13	−0.2484 (4)	0.5296 (2)	0.5436 (3)	0.0357 (7)
H13A	−0.3162	0.5073	0.5620	0.048 (4)*
H13B	−0.1455	0.5138	0.6063	0.048 (4)*
H13C	−0.2749	0.5047	0.4694	0.048 (4)*
C14	0.1677 (3)	0.76221 (19)	0.8091 (2)	0.0262 (6)
C15	0.3070 (3)	0.6152 (2)	0.9370 (3)	0.0296 (6)
C16	0.1055 (3)	0.60419 (18)	0.6968 (3)	0.0256 (6)
H7	−0.101 (3)	0.4472 (19)	0.876 (2)	0.015 (7)*

	U11	U22	U33	U12	U13	U23
Re1	0.01570 (6)	0.01934 (6)	0.02291 (6)	−0.00064 (3)	0.01024 (4)	0.00179 (4)
Br1	0.04358 (17)	0.02932 (15)	0.02861 (14)	−0.00256 (12)	0.02177 (13)	−0.00259 (12)
P1	0.0162 (3)	0.0179 (3)	0.0219 (3)	−0.0005 (2)	0.0105 (2)	0.0015 (3)
O1	0.0244 (9)	0.0195 (9)	0.0297 (10)	0.0009 (7)	0.0155 (8)	0.0024 (8)
O2	0.0290 (11)	0.0302 (11)	0.0431 (13)	−0.0090 (9)	0.0139 (10)	0.0058 (10)
O3	0.0185 (10)	0.0465 (14)	0.0523 (14)	0.0029 (9)	0.0110 (10)	0.0147 (11)
O4	0.0445 (13)	0.0394 (13)	0.0460 (13)	−0.0008 (10)	0.0342 (11)	−0.0043 (10)
C1	0.0184 (12)	0.0227 (13)	0.0240 (13)	−0.0042 (10)	0.0122 (10)	−0.0025 (10)
C2	0.0242 (14)	0.0278 (15)	0.0385 (16)	−0.0006 (11)	0.0194 (12)	0.0019 (12)
C3	0.0220 (14)	0.0438 (18)	0.0406 (17)	−0.0017 (12)	0.0201 (13)	−0.0037 (14)
C4	0.0296 (15)	0.0386 (17)	0.0346 (15)	−0.0143 (13)	0.0225 (13)	−0.0074 (13)
C5	0.0296 (14)	0.0285 (14)	0.0261 (13)	−0.0083 (11)	0.0172 (11)	−0.0033 (11)
C6	0.0238 (12)	0.0200 (13)	0.0227 (12)	−0.0051 (10)	0.0136 (10)	−0.0037 (10)
C7	0.0265 (13)	0.0186 (13)	0.0242 (13)	−0.0033 (10)	0.0147 (11)	−0.0013 (10)
C8	0.0219 (13)	0.0190 (13)	0.0375 (15)	0.0028 (10)	0.0151 (12)	0.0069 (11)
C9	0.0440 (19)	0.0245 (16)	0.054 (2)	0.0056 (13)	0.0251 (17)	−0.0042 (14)
C10	0.0322 (16)	0.0329 (17)	0.0437 (19)	−0.0016 (12)	0.0171 (14)	0.0165 (14)
C11	0.0243 (13)	0.0342 (15)	0.0253 (14)	0.0002 (11)	0.0127 (11)	−0.0040 (12)
C12	0.0294 (16)	0.053 (2)	0.0275 (16)	−0.0033 (14)	0.0055 (13)	−0.0007 (14)
C13	0.0361 (16)	0.0339 (17)	0.0338 (16)	−0.0083 (13)	0.0184 (13)	−0.0114 (13)
C14	0.0182 (12)	0.0294 (15)	0.0268 (14)	0.0000 (10)	0.0106 (10)	0.0037 (11)
C15	0.0241 (14)	0.0283 (15)	0.0338 (15)	−0.0038 (11)	0.0152 (12)	0.0044 (12)
C16	0.0210 (12)	0.0241 (14)	0.0316 (14)	0.0002 (10)	0.0151 (11)	0.0033 (11)

Re1—C14	1.901 (3)	C5—H5	0.9300
Re1—C15	1.943 (3)	C6—C7	1.468 (4)
Re1—C16	1.915 (3)	C7—H7	1.01 (3)
Re1—O1	2.1739 (18)	C8—C9	1.514 (5)
Re1—P1	2.4655 (13)	C8—C10	1.528 (4)
Re1—Br1	2.6116 (6)	C8—H8	0.9800
P1—C1	1.835 (3)	C9—H9A	0.9600
P1—C8	1.842 (3)	C9—H9B	0.9600
P1—C11	1.865 (3)	C9—H9C	0.9600
O1—C7	1.231 (3)	C10—H10A	0.9600
O2—C14	1.153 (3)	C10—H10B	0.9600
O3—C15	1.144 (3)	C10—H10C	0.9600
O4—C16	1.148 (3)	C11—C13	1.517 (4)
C1—C2	1.392 (4)	C11—C12	1.533 (4)
C1—C6	1.406 (4)	C11—H11	0.9800
C2—C3	1.393 (4)	C12—H12A	0.9600
C2—H2	0.9300	C12—H12B	0.9600
C3—C4	1.371 (5)	C12—H12C	0.9600
C3—H3	0.9300	C13—H13A	0.9600
C4—C5	1.383 (4)	C13—H13B	0.9600
C4—H4	0.9300	C13—H13C	0.9600
C5—C6	1.405 (3)
C14—Re1—C16	90.87 (12)	O1—C7—H7	118.4 (15)
C14—Re1—C15	89.06 (12)	C6—C7—H7	112.5 (15)
C16—Re1—C15	89.00 (12)	C9—C8—C10	111.4 (3)
C14—Re1—O1	174.15 (10)	C9—C8—P1	112.9 (2)
C16—Re1—O1	94.97 (9)	C10—C8—P1	109.7 (2)
C15—Re1—O1	91.35 (10)	C9—C8—H8	107.5
C14—Re1—P1	96.71 (8)	C10—C8—H8	107.5
C16—Re1—P1	91.28 (8)	P1—C8—H8	107.5
C15—Re1—P1	174.22 (8)	C8—C9—H9A	109.5
O1—Re1—P1	82.87 (5)	C8—C9—H9B	109.5
C14—Re1—Br1	91.10 (9)	H9A—C9—H9B	109.5
C16—Re1—Br1	177.00 (8)	C8—C9—H9C	109.5
C15—Re1—Br1	88.77 (10)	H9A—C9—H9C	109.5
O1—Re1—Br1	83.07 (5)	H9B—C9—H9C	109.5
P1—Re1—Br1	90.74 (3)	C8—C10—H10A	109.5
C1—P1—C8	104.98 (12)	C8—C10—H10B	109.5
C1—P1—C11	102.31 (13)	H10A—C10—H10B	109.5
C8—P1—C11	104.94 (14)	C8—C10—H10C	109.5
C1—P1—Re1	111.71 (9)	H10A—C10—H10C	109.5
C8—P1—Re1	118.89 (9)	H10B—C10—H10C	109.5
C11—P1—Re1	112.42 (10)	C13—C11—C12	110.0 (3)
C7—O1—Re1	136.60 (18)	C13—C11—P1	111.6 (2)
C2—C1—C6	117.4 (2)	C12—C11—P1	113.6 (2)
C2—C1—P1	120.9 (2)	C13—C11—H11	107.1
C6—C1—P1	121.56 (19)	C12—C11—H11	107.1
C1—C2—C3	121.7 (3)	P1—C11—H11	107.1
C1—C2—H2	119.1	C11—C12—H12A	109.5
C3—C2—H2	119.1	C11—C12—H12B	109.5
C4—C3—C2	120.4 (3)	H12A—C12—H12B	109.5
C4—C3—H3	119.8	C11—C12—H12C	109.5
C2—C3—H3	119.8	H12A—C12—H12C	109.5
C3—C4—C5	119.6 (3)	H12B—C12—H12C	109.5
C3—C4—H4	120.2	C11—C13—H13A	109.5
C5—C4—H4	120.2	C11—C13—H13B	109.5
C4—C5—C6	120.5 (3)	H13A—C13—H13B	109.5
C4—C5—H5	119.7	C11—C13—H13C	109.5
C6—C5—H5	119.7	H13A—C13—H13C	109.5
C5—C6—C1	120.4 (2)	H13B—C13—H13C	109.5
C5—C6—C7	113.0 (2)	O2—C14—Re1	177.4 (3)
C1—C6—C7	126.6 (2)	O3—C15—Re1	178.6 (3)
O1—C7—C6	129.1 (2)	O4—C16—Re1	177.2 (2)

Table 1

Selected bond lengths (Å)

Re1—C14	1.901 (3)
Re1—C15	1.943 (3)
Re1—C16	1.915 (3)
Re1—O1	2.1739 (18)
Re1—P1	2.4655 (13)
Re1—Br1	2.6116 (6)