[Bis(pyridin-2-ylmeth-yl)amine-κ(3)N,N',N'']tricarbonyl-rhenium(I) bromide hemihydrate.

The title compound, fac-[Re(C(12)H(12)N(3))(CO)(3)]Br·0.5H(2)O, crystallizes with a cationic rhenium(I) unit, a bromide ion and half a water mol-ecule, situated on a twofold rotation axis, in the asymmetric unit. The Re(I) atom is facially surrounded by three carbonyl ligands and a tridentate bis-(pyridin-2-ylmeth-yl)amine ligand in a distorted octahedral environment. N-H⋯Br, O-H⋯Br, C-H⋯O and C-H⋯Br hydrogen bonds are present in the crystal structure and π-π stacking is also observed [centroid-centroid distances = 3.669 (1) Å and 4.054 (1) Å], giving rise to a three-dimentional network. The mol-ecules pack in a head-to-head fashion along the ac plane.

Related literature

For the synthesis of the fac-ReI-tricarbonyl synthon, see: Alberto et al. (1996 ▶). For a similar structure, see: Banerjee et al. (2002 ▶). For related structures, see: Raszeja et al. (2011 ▶); Banerjee & Zubieta (2005 ▶); Banerjee et al. (2004 ▶, 2006 ▶); Kunz et al. (2007 ▶); Wei et al. (2006 ▶); Moore et al. (2010 ▶).

Experimental

Crystal data

[Re(C12H12N3)(CO)3]Br·0.5H2O

M = 558.4

Monoclinic,

a = 21.542 (5) Å

b = 11.684 (5) Å

c = 15.126 (5) Å

β = 118.172 (5)°

V = 3356 (2) Å3

Z = 8

Mo Kα radiation

μ = 9.64 mm−1

T = 100 K

0.34 × 0.12 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.265, T max = 0.432

28139 measured reflections

4032 independent reflections

3688 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.014

wR(F 2) = 0.031

S = 1.05

4032 reflections

220 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.14 e Å−3

Δρmin = −0.60 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812019654/ru2033sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019654/ru2033Isup2.hkl

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

[Re(C12H12N3)(CO)3]Br·0.5H2O	F(000) = 2104
Mr = 558.4	Dx = 2.21 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.542 (5) Å	Cell parameters from 9928 reflections
b = 11.684 (5) Å	θ = 2.8–28.3°
c = 15.126 (5) Å	µ = 9.64 mm−1
β = 118.172 (5)°	T = 100 K
V = 3356 (2) Å3	Needle, colourless
Z = 8	0.34 × 0.12 × 0.09 mm

Bruker APEXII CCD diffractometer	3688 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 28°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −28→28
Tmin = 0.265, Tmax = 0.432	k = −15→15
28139 measured reflections	l = −19→17
4032 independent 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)] = 0.014	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.031	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0112P)2 + 4.244P] where P = (Fo2 + 2Fc2)/3
4032 reflections	(Δ/σ)max = 0.004
220 parameters	Δρmax = 1.14 e Å−3
2 restraints	Δρmin = −0.60 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Re1	0.832406 (4)	0.266160 (7)	0.262052 (6)	0.01016 (3)
N1	0.82258 (9)	0.22093 (15)	0.39486 (13)	0.0105 (4)
C3	0.84911 (12)	0.3216 (2)	0.15505 (17)	0.0181 (5)
N3	0.91084 (10)	0.37861 (16)	0.37892 (14)	0.0130 (4)
C2	0.74889 (12)	0.35874 (19)	0.21078 (16)	0.0144 (5)
N2	0.92780 (9)	0.16093 (16)	0.33122 (13)	0.0124 (4)
C25	0.98776 (12)	0.21485 (19)	0.39603 (16)	0.0134 (4)
C21	0.92998 (12)	0.04661 (19)	0.31905 (16)	0.0152 (5)
H21	0.8888	0.0093	0.2746	0.018*
C22	0.99066 (12)	−0.0171 (2)	0.36981 (18)	0.0204 (5)
H22	0.9908	−0.0954	0.3586	0.024*
C24	1.05014 (12)	0.1556 (2)	0.45125 (17)	0.0185 (5)
H24	1.0906	0.194	0.4966	0.022*
C23	1.05138 (12)	0.0382 (2)	0.43790 (18)	0.0210 (5)
H23	1.0927	−0.0029	0.4744	0.025*
C15	0.86452 (11)	0.27820 (18)	0.48059 (16)	0.0125 (4)
C11	0.78009 (11)	0.13816 (19)	0.39807 (16)	0.0139 (4)
H11	0.7496	0.1013	0.3388	0.017*
C12	0.78005 (12)	0.1058 (2)	0.48615 (17)	0.0164 (5)
H12	0.7504	0.048	0.486	0.02*
C16	0.90207 (12)	0.3815 (2)	0.47098 (16)	0.0157 (5)
H16A	0.8758	0.4496	0.4695	0.019*
H16B	0.9481	0.3865	0.5294	0.019*
O2	0.69748 (8)	0.41059 (14)	0.17770 (13)	0.0210 (4)
O1	0.74405 (8)	0.07008 (14)	0.12519 (12)	0.0212 (4)
O3	0.85788 (9)	0.35753 (17)	0.09110 (13)	0.0306 (4)
C1	0.77537 (11)	0.1458 (2)	0.17563 (16)	0.0147 (5)
C26	0.98272 (11)	0.34246 (19)	0.39980 (17)	0.0151 (5)
H26A	1.0168	0.3697	0.4656	0.018*
H26B	0.994	0.3767	0.3507	0.018*
C14	0.86774 (13)	0.2485 (2)	0.57138 (17)	0.0171 (5)
H14	0.8983	0.2868	0.6298	0.02*
C13	0.82505 (12)	0.1613 (2)	0.57449 (17)	0.0185 (5)
H13	0.8266	0.1404	0.6348	0.022*
Br1	0.899690 (12)	0.65619 (2)	0.320564 (16)	0.01760 (5)
O4	1	0.5200 (3)	0.25	0.0578 (10)
H3	0.9062 (16)	0.4465 (17)	0.356 (2)	0.053 (7)*
H4A	0.9723 (15)	0.567 (2)	0.268 (2)	0.053 (7)*

	U11	U22	U33	U12	U13	U23
Re1	0.00954 (5)	0.01156 (5)	0.00819 (4)	0.00126 (3)	0.00319 (3)	0.00068 (3)
N1	0.0101 (9)	0.0109 (9)	0.0103 (8)	0.0031 (7)	0.0046 (7)	0.0003 (7)
C3	0.0121 (11)	0.0238 (13)	0.0156 (11)	0.0040 (9)	0.0042 (9)	0.0025 (10)
N3	0.0124 (9)	0.0106 (9)	0.0138 (9)	−0.0001 (8)	0.0045 (8)	0.0004 (7)
C2	0.0195 (12)	0.0123 (11)	0.0133 (11)	−0.0026 (9)	0.0093 (9)	0.0000 (9)
N2	0.0114 (9)	0.0143 (10)	0.0125 (9)	0.0016 (7)	0.0063 (7)	0.0016 (7)
C25	0.0133 (11)	0.0162 (12)	0.0126 (10)	0.0005 (9)	0.0077 (9)	0.0004 (8)
C21	0.0143 (11)	0.0174 (12)	0.0154 (11)	0.0015 (9)	0.0082 (9)	−0.0008 (9)
C22	0.0226 (13)	0.0181 (13)	0.0221 (12)	0.0049 (10)	0.0119 (11)	0.0009 (10)
C24	0.0133 (11)	0.0246 (13)	0.0163 (11)	0.0016 (10)	0.0060 (9)	0.0001 (10)
C23	0.0161 (12)	0.0261 (14)	0.0196 (12)	0.0105 (10)	0.0073 (10)	0.0037 (10)
C15	0.0100 (10)	0.0127 (11)	0.0137 (10)	0.0038 (8)	0.0049 (9)	−0.0008 (8)
C11	0.0134 (11)	0.0112 (11)	0.0161 (11)	0.0040 (9)	0.0061 (9)	0.0009 (9)
C12	0.0176 (12)	0.0145 (12)	0.0216 (12)	0.0044 (9)	0.0129 (10)	0.0052 (9)
C16	0.0150 (11)	0.0167 (12)	0.0129 (10)	−0.0014 (9)	0.0044 (9)	−0.0046 (9)
O2	0.0154 (9)	0.0152 (9)	0.0295 (9)	0.0036 (7)	0.0081 (7)	0.0045 (7)
O1	0.0191 (9)	0.0223 (9)	0.0174 (8)	−0.0003 (7)	0.0047 (7)	−0.0083 (7)
O3	0.0287 (10)	0.0461 (12)	0.0224 (9)	0.0075 (9)	0.0166 (8)	0.0134 (9)
C1	0.0124 (11)	0.0191 (12)	0.0120 (10)	0.0050 (9)	0.0053 (9)	0.0023 (9)
C26	0.0100 (11)	0.0169 (12)	0.0171 (11)	−0.0013 (9)	0.0053 (9)	−0.0004 (9)
C14	0.0182 (12)	0.0196 (13)	0.0121 (11)	0.0068 (9)	0.0061 (10)	−0.0014 (9)
C13	0.0197 (12)	0.0205 (13)	0.0179 (12)	0.0096 (10)	0.0110 (10)	0.0071 (9)
Br1	0.01889 (12)	0.01679 (12)	0.01454 (11)	0.00078 (9)	0.00578 (9)	0.00349 (8)
O4	0.091 (3)	0.0332 (19)	0.090 (3)	0	0.076 (2)	0

Re1—C1	1.918 (2)	C22—H22	0.93
Re1—C2	1.921 (2)	C24—C23	1.388 (3)
Re1—C3	1.928 (2)	C24—H24	0.93
Re1—N1	2.1819 (19)	C23—H23	0.93
Re1—N2	2.1906 (18)	C15—C14	1.386 (3)
Re1—N3	2.2104 (19)	C15—C16	1.498 (3)
N1—C11	1.348 (3)	C11—C12	1.385 (3)
N1—C15	1.356 (3)	C11—H11	0.93
C3—O3	1.149 (3)	C12—C13	1.386 (3)
N3—C26	1.488 (3)	C12—H12	0.93
N3—C16	1.491 (3)	C16—H16A	0.97
N3—H3	0.850 (18)	C16—H16B	0.97
C2—O2	1.149 (3)	O1—C1	1.155 (3)
N2—C21	1.352 (3)	C26—H26A	0.97
N2—C25	1.353 (3)	C26—H26B	0.97
C25—C24	1.387 (3)	C14—C13	1.389 (3)
C25—C26	1.498 (3)	C14—H14	0.93
C21—C22	1.380 (3)	C13—H13	0.93
C21—H21	0.93	O4—H4A	0.939 (17)
C22—C23	1.385 (3)
C1—Re1—C2	87.77 (10)	C21—C22—H22	120.8
C1—Re1—C3	89.29 (10)	C23—C22—H22	120.8
C2—Re1—C3	88.99 (9)	C25—C24—C23	119.0 (2)
C1—Re1—N1	98.08 (8)	C25—C24—H24	120.5
C2—Re1—N1	91.64 (8)	C23—C24—H24	120.5
C3—Re1—N1	172.62 (8)	C22—C23—C24	119.6 (2)
C1—Re1—N2	93.94 (8)	C22—C23—H23	120.2
C2—Re1—N2	175.80 (8)	C24—C23—H23	120.2
C3—Re1—N2	94.86 (8)	N1—C15—C14	121.6 (2)
N1—Re1—N2	84.33 (7)	N1—C15—C16	116.82 (19)
C1—Re1—N3	169.31 (8)	C14—C15—C16	121.4 (2)
C2—Re1—N3	101.82 (9)	N1—C11—C12	122.6 (2)
C3—Re1—N3	95.54 (9)	N1—C11—H11	118.7
N1—Re1—N3	77.14 (7)	C12—C11—H11	118.7
N2—Re1—N3	76.18 (7)	C11—C12—C13	118.8 (2)
C11—N1—C15	118.46 (19)	C11—C12—H12	120.6
C11—N1—Re1	124.72 (14)	C13—C12—H12	120.6
C15—N1—Re1	116.78 (14)	N3—C16—C15	112.61 (18)
O3—C3—Re1	177.9 (2)	N3—C16—H16A	109.1
C26—N3—C16	112.72 (17)	C15—C16—H16A	109.1
C26—N3—Re1	109.09 (13)	N3—C16—H16B	109.1
C16—N3—Re1	111.98 (13)	C15—C16—H16B	109.1
C26—N3—H3	105 (2)	H16A—C16—H16B	107.8
C16—N3—H3	108 (2)	O1—C1—Re1	176.56 (19)
Re1—N3—H3	109 (2)	N3—C26—C25	111.18 (18)
O2—C2—Re1	177.3 (2)	N3—C26—H26A	109.4
C21—N2—C25	118.42 (19)	C25—C26—H26A	109.4
C21—N2—Re1	125.07 (15)	N3—C26—H26B	109.4
C25—N2—Re1	116.37 (15)	C25—C26—H26B	109.4
N2—C25—C24	121.8 (2)	H26A—C26—H26B	108
N2—C25—C26	115.44 (19)	C15—C14—C13	119.5 (2)
C24—C25—C26	122.7 (2)	C15—C14—H14	120.2
N2—C21—C22	122.8 (2)	C13—C14—H14	120.2
N2—C21—H21	118.6	C12—C13—C14	118.9 (2)
C22—C21—H21	118.6	C12—C13—H13	120.5
C21—C22—C23	118.4 (2)	C14—C13—H13	120.5

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···Br1	0.85 (2)	2.50 (2)	3.340 (2)	170 (3)
O4—H4A···Br1	0.94 (2)	2.31 (2)	3.2429 (18)	171 (3)
C11—H11···O2i	0.93	2.57	3.023 (3)	111
C12—H12···O1ii	0.93	2.57	3.285 (3)	134
C21—H21···O2i	0.93	2.56	3.193 (3)	125
C26—H26A···Br1iii	0.97	2.88	3.767 (3)	153
C26—H26B···O4	0.97	2.31	3.221 (3)	156

Table 1

Selected bond lengths (Å)

Re1—C1	1.918 (2)
Re1—C2	1.921 (2)
Re1—C3	1.928 (2)
Re1—N1	2.1819 (19)
Re1—N2	2.1906 (18)
Re1—N3	2.2104 (19)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯Br1	0.85 (2)	2.50 (2)	3.340 (2)	170 (3)
O4—H4A⋯Br1	0.94 (2)	2.31 (2)	3.2429 (18)	171 (3)
C11—H11⋯O2i	0.93	2.57	3.023 (3)	111
C12—H12⋯O1ii	0.93	2.57	3.285 (3)	134
C21—H21⋯O2i	0.93	2.56	3.193 (3)	125
C26—H26A⋯Br1iii	0.97	2.88	3.767 (3)	153
C26—H26B⋯O4	0.97	2.31	3.221 (3)	156

Symmetry codes: (i) ; (ii) ; (iii) .