Dibromido{2-(morpholin-4-yl)-N-[1-(2-pyrid-yl)ethyl-idene]ethanamine-κN,N',N''}cadmium.

The Cd(II) ion in the title compound, [CdBr(2)(C(13)H(19)N(3)O)], is five-coordinated by the N,N',N''-tridentate Schiff base ligand and two Br atoms in a distorted square-pyramidal geometry. In the crystal, inter-molecular C-H⋯O and C-H⋯Br hydrogen bonds link adjacent mol-ecules into layers parallel to the ab plane. An intra-molecular C-H⋯Br inter-action is also observed.

Related literature

For the crystal structure of the analogous CdCl2 complex, see: Ikmal Hisham et al. (2010 ▶). For the crystal structures of similar CdBr2 complexes, see: Bermejo et al. (1999 ▶, 2003 ▶). For a description of the geometry of complexes with five-coordinate metal atoms, see: Addison et al. (1984 ▶).

Experimental

Crystal data

[CdBr2(C13H19N3O)]

M = 505.53

Orthorhombic,

a = 9.1906 (8) Å

b = 12.2604 (10) Å

c = 14.7499 (12) Å

V = 1662.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 6.12 mm−1

T = 100 K

0.33 × 0.27 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.237, T max = 0.389

20236 measured reflections

3642 independent reflections

3445 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.041

S = 1.09

3642 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.54 e Å−3

Absolute structure: Flack (1983 ▶), 1556 Friedel pairs

Flack parameter: 0.023 (9)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100554X/bg2390sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100554X/bg2390Isup2.hkl

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

[CdBr2(C13H19N3O)]	F(000) = 976
Mr = 505.53	Dx = 2.020 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5963 reflections
a = 9.1906 (8) Å	θ = 2.6–30.7°
b = 12.2604 (10) Å	µ = 6.12 mm−1
c = 14.7499 (12) Å	T = 100 K
V = 1662.0 (2) Å3	Block, colorless
Z = 4	0.33 × 0.27 × 0.19 mm

Bruker APEXII CCD diffractometer	3642 independent reflections
Radiation source: fine-focus sealed tube	3445 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.237, Tmax = 0.389	k = −15→15
20236 measured reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021	H-atom parameters constrained
wR(F2) = 0.041	w = 1/[σ2(Fo2) + (0.006P)2 + 1.6071P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
3642 reflections	Δρmax = 0.73 e Å−3
182 parameters	Δρmin = −0.54 e Å−3
0 restraints	Absolute structure: Flack (1983), 1556 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.023 (9)

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.

	x	y	z	Uiso*/Ueq
Cd1	0.03808 (2)	0.00442 (2)	0.919266 (13)	0.01367 (5)
Br1	−0.21463 (3)	0.00329 (4)	0.84484 (2)	0.02368 (7)
Br2	0.07480 (3)	−0.00774 (4)	1.092730 (19)	0.02169 (7)
O1	−0.0135 (3)	−0.34931 (19)	0.93888 (17)	0.0151 (6)
N1	0.0632 (3)	0.1977 (2)	0.90768 (19)	0.0163 (6)
N2	0.2634 (3)	0.0505 (2)	0.86157 (18)	0.0143 (6)
N3	0.1405 (3)	−0.1675 (2)	0.85991 (18)	0.0127 (6)
C1	−0.0399 (4)	0.2704 (3)	0.9296 (2)	0.0194 (7)
H1	−0.1334	0.2443	0.9463	0.023*
C2	−0.0157 (5)	0.3826 (3)	0.9291 (3)	0.0225 (9)
H2	−0.0908	0.4322	0.9451	0.027*
C3	0.1197 (4)	0.4192 (3)	0.9049 (3)	0.0240 (8)
H3	0.1400	0.4951	0.9051	0.029*
C4	0.2272 (4)	0.3455 (3)	0.8800 (2)	0.0209 (8)
H4	0.3206	0.3701	0.8616	0.025*
C5	0.1948 (4)	0.2342 (3)	0.8827 (2)	0.0145 (7)
C6	0.3044 (4)	0.1495 (3)	0.8549 (2)	0.0146 (7)
C7	0.4496 (4)	0.1874 (3)	0.8209 (3)	0.0253 (8)
H7A	0.4380	0.2199	0.7606	0.038*
H7B	0.5162	0.1252	0.8172	0.038*
H7C	0.4894	0.2420	0.8627	0.038*
C8	0.3532 (4)	−0.0426 (2)	0.8376 (2)	0.0164 (7)
H8A	0.4034	−0.0709	0.8922	0.020*
H8B	0.4278	−0.0207	0.7928	0.020*
C9	0.2553 (4)	−0.1303 (3)	0.7977 (2)	0.0176 (7)
H9A	0.2093	−0.1016	0.7419	0.021*
H9B	0.3160	−0.1937	0.7802	0.021*
C10	0.2041 (4)	−0.2361 (3)	0.9323 (2)	0.0167 (7)
H10A	0.2692	−0.1912	0.9705	0.020*
H10B	0.2630	−0.2950	0.9047	0.020*
C11	0.0853 (4)	−0.2858 (3)	0.9907 (2)	0.0181 (7)
H11A	0.1303	−0.3323	1.0378	0.022*
H11B	0.0313	−0.2267	1.0217	0.022*
C12	−0.0787 (4)	−0.2837 (3)	0.8695 (2)	0.0177 (7)
H12A	−0.1356	−0.2242	0.8978	0.021*
H12B	−0.1463	−0.3290	0.8333	0.021*
C13	0.0361 (4)	−0.2354 (3)	0.8079 (2)	0.0174 (7)
H13A	0.0894	−0.2950	0.7770	0.021*
H13B	−0.0114	−0.1901	0.7609	0.021*

	U11	U22	U33	U12	U13	U23
Cd1	0.01446 (9)	0.01227 (9)	0.01429 (9)	0.00005 (13)	0.00293 (7)	0.00048 (13)
Br1	0.01711 (14)	0.02244 (15)	0.03150 (16)	0.0017 (2)	−0.00424 (12)	0.0024 (2)
Br2	0.02749 (16)	0.02287 (17)	0.01472 (13)	0.00513 (19)	−0.00019 (11)	−0.00188 (19)
O1	0.0147 (14)	0.0118 (11)	0.0190 (14)	−0.0018 (10)	−0.0005 (10)	0.0025 (10)
N1	0.0184 (15)	0.0152 (13)	0.0154 (14)	0.0012 (11)	0.0020 (12)	0.0039 (11)
N2	0.0147 (15)	0.0163 (13)	0.0120 (13)	0.0018 (11)	0.0003 (11)	0.0003 (11)
N3	0.0155 (14)	0.0100 (13)	0.0128 (14)	−0.0002 (11)	0.0015 (11)	0.0010 (11)
C1	0.0217 (18)	0.0191 (16)	0.0173 (18)	0.0019 (15)	0.0056 (15)	0.0012 (14)
C2	0.032 (2)	0.0147 (16)	0.021 (2)	0.0080 (16)	−0.0011 (17)	0.0001 (15)
C3	0.034 (2)	0.0116 (15)	0.027 (2)	−0.0018 (14)	−0.0087 (17)	−0.0008 (15)
C4	0.0203 (18)	0.0163 (17)	0.0260 (19)	−0.0043 (14)	−0.0043 (15)	0.0000 (14)
C5	0.0152 (18)	0.0154 (16)	0.0128 (17)	0.0028 (13)	−0.0030 (15)	0.0017 (14)
C6	0.0145 (17)	0.0176 (16)	0.0116 (16)	−0.0009 (13)	−0.0011 (13)	0.0041 (13)
C7	0.0204 (19)	0.0187 (17)	0.037 (2)	−0.0055 (15)	0.0066 (17)	0.0005 (15)
C8	0.0134 (17)	0.0135 (15)	0.0224 (18)	0.0018 (12)	0.0040 (14)	0.0031 (13)
C9	0.0202 (18)	0.0164 (17)	0.0162 (17)	0.0017 (13)	0.0064 (14)	−0.0013 (14)
C10	0.0169 (17)	0.0155 (16)	0.0178 (18)	0.0023 (13)	−0.0007 (15)	0.0045 (14)
C11	0.0149 (17)	0.0172 (17)	0.0223 (18)	−0.0020 (13)	−0.0011 (14)	0.0052 (14)
C12	0.0183 (18)	0.0150 (16)	0.0198 (18)	−0.0016 (13)	−0.0013 (15)	−0.0005 (13)
C13	0.0210 (18)	0.0165 (16)	0.0147 (16)	0.0011 (14)	−0.0007 (14)	−0.0049 (13)

Cd1—N2	2.309 (3)	C4—H4	0.9500
Cd1—N1	2.388 (3)	C5—C6	1.504 (5)
Cd1—N3	2.469 (3)	C6—C7	1.500 (5)
Cd1—Br1	2.5690 (4)	C7—H7A	0.9800
Cd1—Br2	2.5851 (4)	C7—H7B	0.9800
O1—C11	1.420 (4)	C7—H7C	0.9800
O1—C12	1.433 (4)	C8—C9	1.520 (5)
N1—C1	1.340 (4)	C8—H8A	0.9900
N1—C5	1.341 (4)	C8—H8B	0.9900
N2—C6	1.275 (4)	C9—H9A	0.9900
N2—C8	1.452 (4)	C9—H9B	0.9900
N3—C9	1.471 (4)	C10—C11	1.518 (5)
N3—C10	1.479 (4)	C10—H10A	0.9900
N3—C13	1.484 (4)	C10—H10B	0.9900
C1—C2	1.393 (5)	C11—H11A	0.9900
C1—H1	0.9500	C11—H11B	0.9900
C2—C3	1.370 (6)	C12—C13	1.514 (5)
C2—H2	0.9500	C12—H12A	0.9900
C3—C4	1.388 (5)	C12—H12B	0.9900
C3—H3	0.9500	C13—H13A	0.9900
C4—C5	1.397 (5)	C13—H13B	0.9900
N2—Cd1—N1	69.15 (9)	C6—C7—H7B	109.5
N2—Cd1—N3	74.71 (9)	H7A—C7—H7B	109.5
N1—Cd1—N3	141.76 (9)	C6—C7—H7C	109.5
N2—Cd1—Br1	130.89 (7)	H7A—C7—H7C	109.5
N1—Cd1—Br1	93.56 (7)	H7B—C7—H7C	109.5
N3—Cd1—Br1	100.87 (6)	N2—C8—C9	108.3 (3)
N2—Cd1—Br2	105.18 (7)	N2—C8—H8A	110.0
N1—Cd1—Br2	96.63 (7)	C9—C8—H8A	110.0
N3—Cd1—Br2	104.59 (6)	N2—C8—H8B	110.0
Br1—Cd1—Br2	122.729 (12)	C9—C8—H8B	110.0
C11—O1—C12	110.1 (2)	H8A—C8—H8B	108.4
C1—N1—C5	118.8 (3)	N3—C9—C8	113.7 (3)
C1—N1—Cd1	125.1 (2)	N3—C9—H9A	108.8
C5—N1—Cd1	116.0 (2)	C8—C9—H9A	108.8
C6—N2—C8	124.2 (3)	N3—C9—H9B	108.8
C6—N2—Cd1	121.8 (2)	C8—C9—H9B	108.8
C8—N2—Cd1	114.02 (19)	H9A—C9—H9B	107.7
C9—N3—C10	110.1 (3)	N3—C10—C11	110.7 (3)
C9—N3—C13	108.4 (3)	N3—C10—H10A	109.5
C10—N3—C13	108.1 (2)	C11—C10—H10A	109.5
C9—N3—Cd1	103.29 (18)	N3—C10—H10B	109.5
C10—N3—Cd1	112.3 (2)	C11—C10—H10B	109.5
C13—N3—Cd1	114.57 (19)	H10A—C10—H10B	108.1
N1—C1—C2	122.8 (3)	O1—C11—C10	112.0 (3)
N1—C1—H1	118.6	O1—C11—H11A	109.2
C2—C1—H1	118.6	C10—C11—H11A	109.2
C3—C2—C1	118.0 (4)	O1—C11—H11B	109.2
C3—C2—H2	121.0	C10—C11—H11B	109.2
C1—C2—H2	121.0	H11A—C11—H11B	107.9
C2—C3—C4	120.1 (3)	O1—C12—C13	110.9 (3)
C2—C3—H3	119.9	O1—C12—H12A	109.5
C4—C3—H3	119.9	C13—C12—H12A	109.5
C3—C4—C5	118.4 (3)	O1—C12—H12B	109.5
C3—C4—H4	120.8	C13—C12—H12B	109.5
C5—C4—H4	120.8	H12A—C12—H12B	108.0
N1—C5—C4	121.7 (3)	N3—C13—C12	111.1 (3)
N1—C5—C6	116.6 (3)	N3—C13—H13A	109.4
C4—C5—C6	121.6 (3)	C12—C13—H13A	109.4
N2—C6—C7	125.7 (3)	N3—C13—H13B	109.4
N2—C6—C5	116.0 (3)	C12—C13—H13B	109.4
C7—C6—C5	118.2 (3)	H13A—C13—H13B	108.0
C6—C7—H7A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.95	2.42	3.132 (4)	131
C7—H7B···Br1ii	0.98	2.92	3.840 (4)	157
C10—H10A···O1iii	0.99	2.45	3.383 (4)	156
C11—H11B···Br2	0.99	2.91	3.727 (4)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.95	2.42	3.132 (4)	131
C7—H7B⋯Br1ii	0.98	2.92	3.840 (4)	157
C10—H10A⋯O1iii	0.99	2.45	3.383 (4)	156
C11—H11B⋯Br2	0.99	2.91	3.727 (4)	141

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