Tetra-aqua-(1,10-phenanthroline-κN,N')magnesium(II) bis-[(2,4-dichloro-phen-yl)acetate].

In the mononuclear title complex, [Mg(C(12)H(8)N(2))(H(2)O)(4)](C(8)H(5)Cl(2)O(2))(2), each Mg(II) ion is hexa-coordinated by two N atoms from a 1,10-phenanthroline ligand [Mg-N = 2.233 (2) Å] and four water mol-ecules [Mg-OW = 2.033 (2) and 2.043 (1) Å] in a distorted octa-hedral geometry. A twofold rotation axis passes through the Mg atom. In the crystal structure, the cations and anions are linked by inter-molecular O-H⋯O hydrogen bonds and π-π stacking inter-actions [centroid-centroid distance = 3.804 (2) Å] into layers parallel to the ac plane.

Related literature

For related literature, see: Castellari et al. (1999 ▶); Kopylovich et al. (2003 ▶); Sharma et al. (2007 ▶); Zhou et al. (2007 ▶).

Experimental

Crystal data

[Mg(C12H8N2)(H2O)4](C8H5Cl2O2)2

M = 684.62

Monoclinic,

a = 28.926 (1) Å

b = 14.0447 (6) Å

c = 7.6074 (3) Å

β = 94.785 (1)°

V = 3079.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 273 (2) K

0.34 × 0.26 × 0.18 mm

Data collection

Bruker P4 diffractometer

Absorption correction: empirical [OR multi-scan](using intensity measurements) (SADABS; Sheldrick, 1996 ▶) T min = 0.867, T max = 0.921

10955 measured reflections

3732 independent reflections

2619 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.117

S = 1.02

3732 reflections

207 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022150/im2068sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022150/im2068Isup2.hkl

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

[Mg(C12H8N2)(H2O)4](C8H5Cl2O2)2	F000 = 1408
Mr = 684.62	Dx = 1.477 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 10366 reflections
a = 28.926 (1) Å	θ = 2.8–28.2º
b = 14.0447 (6) Å	µ = 0.46 mm−1
c = 7.6074 (3) Å	T = 273 (2) K
β = 94.785 (1)º	Prism, colorless
V = 3079.8 (2) Å3	0.34 × 0.26 × 0.18 mm
Z = 4

Bruker P4 diffractometer	3732 independent reflections
Radiation source: fine-focus sealed tube	2619 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.021
Detector resolution: 10.000 pixels mm-1	θmax = 28.2º
T = 273(2) K	θmin = 2.8º
ω scans	h = −38→33
Absorption correction: empirical (using intensity measurements)(SADABS; Sheldrick, 1996)	k = −18→18
Tmin = 0.867, Tmax = 0.921	l = −9→10
10955 measured reflections

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0514P)2 + 1.7903P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3732 reflections	Δρmax = 0.36 e Å−3
207 parameters	Δρmin = −0.47 e Å−3
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0001 (1)

	x	y	z	Uiso*/Ueq
Mg1	0.5000	0.70119 (6)	0.2500	0.0377 (2)
Cl1	0.30958 (2)	0.68124 (5)	0.95908 (8)	0.06695 (19)
Cl2	0.25982 (3)	0.96821 (5)	0.52259 (13)	0.0957 (3)
O1	0.42857 (5)	0.68303 (10)	0.76580 (19)	0.0501 (3)
O1W	0.44481 (6)	0.61206 (10)	0.20734 (19)	0.0613 (4)
O2W	0.50764 (5)	0.69659 (11)	−0.01445 (17)	0.0480 (3)
O2	0.41678 (5)	0.54277 (10)	0.88709 (19)	0.0544 (4)
N1	0.45496 (5)	0.82808 (11)	0.1896 (2)	0.0423 (4)
C1	0.41135 (7)	0.82785 (17)	0.1205 (3)	0.0577 (6)
H1A	0.3966	0.7697	0.0991	0.069*
C2	0.38664 (9)	0.9115 (2)	0.0787 (4)	0.0733 (7)
H2A	0.3562	0.9084	0.0293	0.088*
C3	0.40715 (9)	0.9969 (2)	0.1101 (3)	0.0705 (7)
H3A	0.3907	1.0527	0.0846	0.085*
C4	0.45322 (8)	1.00081 (15)	0.1812 (3)	0.0552 (5)
C5	0.47614 (6)	0.91362 (12)	0.2161 (2)	0.0392 (4)
C6	0.47783 (10)	1.08762 (15)	0.2176 (4)	0.0734 (8)
H6A	0.4627	1.1453	0.1957	0.088*
C7	0.33544 (7)	0.68867 (14)	0.6254 (3)	0.0457 (5)
C8	0.31108 (6)	0.73310 (14)	0.7514 (3)	0.0456 (4)
C9	0.28790 (7)	0.81845 (15)	0.7222 (3)	0.0544 (5)
H9A	0.2720	0.8466	0.8101	0.065*
C10	0.28898 (7)	0.86044 (16)	0.5596 (3)	0.0603 (6)
C11	0.31228 (9)	0.81981 (19)	0.4301 (3)	0.0698 (7)
H11A	0.3128	0.8491	0.3206	0.084*
C12	0.33515 (8)	0.73431 (19)	0.4637 (3)	0.0628 (6)
H12A	0.3508	0.7066	0.3750	0.075*
C13	0.36083 (7)	0.59691 (15)	0.6623 (3)	0.0532 (5)
H13A	0.3682	0.5690	0.5514	0.064*
H13B	0.3406	0.5530	0.7176	0.064*
C14	0.40558 (7)	0.60887 (14)	0.7815 (2)	0.0413 (4)
H2W1	0.4831 (4)	0.6910 (16)	−0.083 (2)	0.062*
H2W2	0.5312 (4)	0.6889 (16)	−0.071 (2)	0.062*
H1W1	0.4397 (8)	0.5689 (12)	0.2818 (19)	0.062*
H1W2	0.4390 (8)	0.5895 (14)	0.1044 (13)	0.062*

	U11	U22	U33	U12	U13	U23
Mg1	0.0472 (5)	0.0291 (4)	0.0373 (4)	0.000	0.0060 (4)	0.000
Cl1	0.0679 (4)	0.0739 (4)	0.0613 (4)	0.0017 (3)	0.0193 (3)	0.0105 (3)
Cl2	0.0834 (5)	0.0587 (4)	0.1391 (7)	0.0047 (3)	−0.0259 (5)	0.0226 (4)
O1	0.0404 (7)	0.0532 (8)	0.0568 (9)	−0.0033 (6)	0.0054 (6)	0.0051 (6)
O1W	0.0958 (12)	0.0482 (8)	0.0394 (8)	−0.0322 (8)	0.0021 (8)	0.0015 (6)
O2W	0.0441 (8)	0.0631 (9)	0.0373 (7)	0.0031 (7)	0.0062 (6)	0.0027 (6)
O2	0.0743 (10)	0.0418 (7)	0.0463 (8)	0.0029 (7)	−0.0003 (7)	−0.0041 (6)
N1	0.0421 (9)	0.0402 (8)	0.0452 (9)	0.0014 (7)	0.0074 (7)	0.0005 (7)
C1	0.0458 (12)	0.0650 (14)	0.0623 (14)	0.0013 (10)	0.0035 (10)	0.0007 (11)
C2	0.0489 (13)	0.095 (2)	0.0760 (17)	0.0240 (14)	0.0029 (11)	0.0105 (15)
C3	0.0744 (17)	0.0695 (16)	0.0687 (16)	0.0356 (14)	0.0129 (13)	0.0151 (13)
C4	0.0762 (15)	0.0408 (10)	0.0513 (12)	0.0170 (10)	0.0204 (11)	0.0065 (9)
C5	0.0504 (10)	0.0320 (8)	0.0368 (9)	0.0040 (8)	0.0137 (7)	0.0022 (7)
C6	0.114 (2)	0.0323 (10)	0.0777 (18)	0.0144 (11)	0.0287 (16)	0.0067 (11)
C7	0.0366 (10)	0.0509 (11)	0.0486 (11)	−0.0043 (8)	−0.0024 (8)	−0.0053 (9)
C8	0.0377 (10)	0.0482 (11)	0.0509 (11)	−0.0053 (8)	0.0037 (8)	0.0014 (9)
C9	0.0407 (11)	0.0514 (12)	0.0710 (15)	−0.0013 (9)	0.0041 (10)	−0.0032 (10)
C10	0.0440 (12)	0.0514 (12)	0.0827 (17)	−0.0039 (10)	−0.0108 (11)	0.0088 (12)
C11	0.0623 (15)	0.0838 (18)	0.0612 (15)	−0.0099 (13)	−0.0061 (12)	0.0236 (13)
C12	0.0558 (13)	0.0827 (17)	0.0498 (12)	−0.0009 (12)	0.0034 (10)	−0.0016 (12)
C13	0.0486 (12)	0.0500 (12)	0.0602 (13)	0.0000 (9)	−0.0006 (9)	−0.0155 (10)
C14	0.0430 (10)	0.0424 (10)	0.0395 (10)	0.0058 (8)	0.0095 (8)	−0.0086 (8)

Mg1—N1	2.2327 (16)	C3—C4	1.397 (3)
Mg1—O1W	2.0333 (15)	C3—H3A	0.9300
Mg1—O2W	2.0432 (13)	C4—C5	1.407 (3)
Mg1—N1i	2.2327 (16)	C4—C6	1.427 (3)
Mg1—O1Wi	2.0333 (15)	C5—C5i	1.433 (4)
Mg1—O2Wi	2.0432 (13)	C6—C6i	1.335 (6)
Cl1—C8	1.744 (2)	C6—H6A	0.9300
Cl2—C10	1.744 (2)	C7—C8	1.385 (3)
N1—C1	1.325 (3)	C7—C12	1.386 (3)
N1—C5	1.356 (2)	C7—C13	1.498 (3)
O1—C14	1.247 (2)	C8—C9	1.382 (3)
O2—C14	1.252 (2)	C9—C10	1.373 (3)
O1W—H1W1	0.851 (9)	C9—H9A	0.9300
O1W—H1W2	0.849 (9)	C10—C11	1.365 (4)
O2W—H2W1	0.849 (9)	C11—C12	1.384 (3)
O2W—H2W2	0.841 (9)	C11—H11A	0.9300
C1—C2	1.399 (3)	C12—H12A	0.9300
C1—H1A	0.9300	C13—C14	1.527 (3)
C2—C3	1.350 (4)	C13—H13A	0.9700
C2—H2A	0.9300	C13—H13B	0.9700
N1i—Mg1—N1	74.07 (8)	C3—C4—C6	123.6 (2)
O1W—Mg1—N1	91.24 (6)	C4—C3—H3A	120.2
O1Wi—Mg1—N1	163.97 (7)	C4—C5—C5i	119.50 (13)
O1W—Mg1—O1Wi	104.01 (11)	C4—C6—H6A	119.3
O1W—Mg1—O2W	88.36 (6)	C5—N1—Mg1	115.34 (12)
O1Wi—Mg1—O2W	89.41 (6)	C5—C4—C6	119.2 (2)
O2Wi—Mg1—N1	96.82 (6)	C6i—C6—C4	121.32 (14)
O2W—Mg1—N1	86.08 (6)	C6i—C6—H6A	119.3
O2Wi—Mg1—O2W	176.38 (9)	C7—C8—Cl1	119.45 (15)
Mg1—O1W—H1W1	120.6 (15)	C7—C12—H12A	118.9
Mg1—O1W—H1W2	118.1 (15)	C7—C13—C14	113.25 (16)
Mg1—O2W—H2W1	117.2 (14)	C7—C13—H13A	108.9
Mg1—O2W—H2W2	131.6 (14)	C7—C13—H13B	108.9
N1—C1—C2	122.7 (2)	C8—C7—C12	116.1 (2)
N1—C1—H1A	118.7	C8—C7—C13	121.84 (19)
N1—C5—C4	122.90 (18)	C8—C9—H9A	121.0
N1—C5—C5i	117.60 (10)	C9—C8—C7	123.2 (2)
O1—C14—O2	124.69 (18)	C9—C8—Cl1	117.34 (17)
O1—C14—C13	117.88 (18)	C9—C10—Cl2	118.1 (2)
O2—C14—C13	117.42 (18)	C10—C9—C8	118.0 (2)
O1W—Mg1—N1i	163.97 (7)	C10—C9—H9A	121.0
O1Wi—Mg1—N1i	91.24 (6)	C10—C11—C12	119.1 (2)
O1W—Mg1—O2Wi	89.41 (6)	C10—C11—H11A	120.5
O1Wi—Mg1—O2Wi	88.36 (6)	C11—C10—C9	121.4 (2)
O2Wi—Mg1—N1i	86.08 (6)	C11—C10—Cl2	120.5 (2)
O2W—Mg1—N1i	96.82 (6)	C11—C12—C7	122.2 (2)
C1—N1—C5	117.67 (17)	C11—C12—H12A	118.9
C1—N1—Mg1	126.82 (14)	C12—C7—C13	122.1 (2)
C1—C2—H2A	120.1	C12—C11—H11A	120.5
C2—C1—H1A	118.7	C14—C13—H13A	108.9
C2—C3—C4	119.7 (2)	C14—C13—H13B	108.9
C2—C3—H3A	120.2	H1W1—O1W—H1W2	108.5 (14)
C3—C2—C1	119.8 (2)	H2W1—O2W—H2W2	110.2 (14)
C3—C2—H2A	120.1	H13A—C13—H13B	107.7
C3—C4—C5	117.2 (2)
Mg1—N1—C1—C2	−176.53 (18)	C5—N1—C1—C2	−1.5 (3)
Mg1—N1—C5—C4	178.64 (15)	C5—C4—C6—C6i	0.6 (5)
Mg1—N1—C5—C5i	−1.9 (3)	C6—C4—C5—N1	178.3 (2)
N1i—Mg1—N1—C1	175.8 (2)	C6—C4—C5—C5i	−1.2 (3)
N1i—Mg1—N1—C5	0.66 (9)	C7—C8—C9—C10	0.5 (3)
N1—C1—C2—C3	−0.6 (4)	C7—C13—C14—O1	−35.1 (3)
O1W—Mg1—N1—C1	−10.68 (18)	C7—C13—C14—O2	145.54 (19)
O1Wi—Mg1—N1—C1	151.6 (2)	C8—C7—C12—C11	0.6 (3)
O1W—Mg1—N1—C5	174.14 (13)	C8—C7—C13—C14	−74.1 (2)
O1Wi—Mg1—N1—C5	−23.6 (3)	C8—C9—C10—C11	−0.2 (3)
O2Wi—Mg1—N1—C1	−100.24 (18)	C8—C9—C10—Cl2	−179.92 (15)
O2W—Mg1—N1—C1	77.59 (18)	C9—C10—C11—C12	0.2 (4)
O2Wi—Mg1—N1—C5	84.59 (13)	C10—C11—C12—C7	−0.4 (4)
O2W—Mg1—N1—C5	−97.59 (13)	Cl1—C8—C9—C10	179.64 (16)
C1—N1—C5—C4	3.0 (3)	C12—C7—C8—C9	−0.7 (3)
C1—N1—C5—C5i	−177.5 (2)	Cl2—C10—C11—C12	179.89 (17)
C1—C2—C3—C4	1.2 (4)	C13—C7—C8—C9	179.01 (18)
C2—C3—C4—C5	0.2 (4)	C12—C7—C8—Cl1	−179.82 (15)
C2—C3—C4—C6	179.5 (2)	C12—C7—C13—C14	105.5 (2)
C3—C4—C5—N1	−2.4 (3)	C13—C7—C8—Cl1	−0.2 (3)
C3—C4—C6—C6i	−178.7 (3)	C13—C7—C12—C11	−179.0 (2)
C3—C4—C5—C5i	178.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H2W1···O1ii	0.849 (9)	1.876 (9)	2.725 (2)	178 (2)
O2W—H2W2···O1i	0.841 (9)	1.96 (1)	2.772 (2)	161 (2)
O1W—H1W1···O2iii	0.851 (9)	1.91 (1)	2.728 (2)	162 (2)
O1W—H1W2···O2ii	0.849 (9)	1.84 (1)	2.685 (2)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2W—H2W1⋯O1i	0.849 (9)	1.876 (9)	2.725 (2)	178 (2)
O2W—H2W2⋯O1ii	0.841 (9)	1.96 (1)	2.772 (2)	161 (2)
O1W—H1W1⋯O2iii	0.851 (9)	1.91 (1)	2.728 (2)	162 (2)
O1W—H1W2⋯O2i	0.849 (9)	1.84 (1)	2.685 (2)	171 (2)

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