Bis{μ-2,2'-[1,1'-(ethane-1,2-diyldinitrilo)diethyl-idyne]diphenolato-κO,N,N',O':O}bis-[chloridomanganese(III)].

The title compound, [Mn(2)(C(18)H(18)N(2)O(2))(2)Cl(2)], was synthesized by the reaction between manganese(II) o-chloro-benzoate and the Schiff base generated in situ by the condensation of ethane-1,2-diamine and o-hydroxy-acetophenone. The centrosymmetric dimer contains two Jahn-Teller-distorted mangan-ese(III) ions, each in an octa-hedral geometry, connected through two phen-oxy bridges from two ligands.

Related literature

For related literature, see: Christou (2005 ▶); Horwitz et al. (1995 ▶); Jacobsen et al. (1991 ▶); Larrow & Jacobsen (2004 ▶); Panja et al. (2003 ▶); Pecoraro & Butler (1986 ▶); Saha et al. (2004 ▶); Triller et al. (2002 ▶); Vites & Lynam (1998 ▶); Zhang et al. (1990 ▶).

Experimental

Crystal data

[Mn2(C18H18N2O2)2Cl2]

M = 769.47

Triclinic,

a = 7.8261 (3) Å

b = 9.8046 (3) Å

c = 11.2372 (4) Å

α = 97.207 (2)°

β = 94.701 (2)°

γ = 108.081 (2)°

V = 806.49 (5) Å3

Z = 1

Cu Kα radiation

μ = 8.29 mm−1

T = 100 (2) K

0.28 × 0.14 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SAINT-Plus; Bruker, 2004 ▶) T min = 0.205, T max = 0.390 (expected range = 0.165–0.313)

12822 measured reflections

2781 independent reflections

2733 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.088

S = 1.10

2781 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808000226/hy2115sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000226/hy2115Isup2.hkl

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

[Mn2(C18H18N2O2)2Cl2]	Z = 1
Mr = 769.47	F000 = 396
Triclinic, P1	Dx = 1.584 Mg m−3
Hall symbol: -P 1	Cu Kα radiation λ = 1.54178 Å
a = 7.8261 (3) Å	Cell parameters from 2781 reflections
b = 9.8046 (3) Å	θ = 9.8–71.6º
c = 11.2372 (4) Å	µ = 8.29 mm−1
α = 97.207 (2)º	T = 100 (2) K
β = 94.701 (2)º	Prism, brown
γ = 108.081 (2)º	0.28 × 0.14 × 0.14 mm
V = 806.49 (5) Å3

Bruker SMART APEXII CCD diffractometer	2781 independent reflections
Radiation source: fine-focus sealed tube	2733 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
T = 100(2) K	θmax = 67.0º
φ and ω scans	θmin = 4.0º
Absorption correction: multi-scan(SAINT-Plus; Bruker, 2004)	h = −9→9
Tmin = 0.205, Tmax = 0.390	k = −11→11
12822 measured reflections	l = −13→12

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)] = 0.032	H-atom parameters constrained
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.0396P)2 + 1.0982P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
2781 reflections	Δρmax = 0.39 e Å−3
219 parameters	Δρmin = −0.44 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
Mn1	0.03321 (5)	0.93493 (4)	0.13283 (3)	0.00849 (13)
Cl1	0.23277 (7)	0.82169 (6)	0.23406 (5)	0.01447 (15)
O1	0.1568 (2)	0.96398 (17)	−0.00716 (14)	0.0108 (3)
O2	0.1517 (2)	1.12309 (17)	0.21677 (14)	0.0118 (3)
N1	−0.1287 (3)	0.7452 (2)	0.04014 (18)	0.0107 (4)
N2	−0.1560 (3)	0.9047 (2)	0.24675 (17)	0.0109 (4)
C18	0.1226 (3)	1.1893 (3)	0.3192 (2)	0.0114 (5)
C12	−0.1614 (3)	0.9876 (3)	0.3457 (2)	0.0107 (5)
C5	0.1437 (3)	0.6051 (3)	−0.1622 (2)	0.0137 (5)
H5	0.0687	0.5063	−0.1770	0.016*
C7	−0.0921 (3)	0.6659 (2)	−0.0498 (2)	0.0112 (5)
C8	−0.2364 (3)	0.5291 (3)	−0.1141 (2)	0.0142 (5)
H8A	−0.2528	0.4528	−0.0634	0.021*
H8B	−0.1993	0.4970	−0.1910	0.021*
H8C	−0.3509	0.5488	−0.1297	0.021*
C2	0.3629 (3)	0.8946 (3)	−0.1229 (2)	0.0119 (5)
H2	0.4379	0.9934	−0.1109	0.014*
C1	0.2018 (3)	0.8569 (2)	−0.0705 (2)	0.0102 (4)
C11	−0.3108 (3)	0.9334 (3)	0.4225 (2)	0.0160 (5)
H11A	−0.4250	0.9375	0.3830	0.024*
H11B	−0.2802	0.9946	0.5022	0.024*
H11C	−0.3238	0.8328	0.4321	0.024*
C9	−0.3112 (3)	0.7098 (3)	0.0770 (2)	0.0135 (5)
H9A	−0.3738	0.6036	0.0577	0.016*
H9B	−0.3829	0.7588	0.0323	0.016*
C13	−0.0262 (3)	1.1327 (3)	0.3837 (2)	0.0123 (5)
C14	−0.0442 (3)	1.2227 (3)	0.4882 (2)	0.0158 (5)
H14	−0.1439	1.1874	0.5315	0.019*
C6	0.0872 (3)	0.7094 (3)	−0.0912 (2)	0.0106 (4)
C17	0.2500 (3)	1.3270 (3)	0.3664 (2)	0.0141 (5)
H17	0.3542	1.3622	0.3270	0.017*
C10	−0.2963 (3)	0.7598 (3)	0.2119 (2)	0.0139 (5)
H10A	−0.4146	0.7652	0.2331	0.017*
H10B	−0.2637	0.6889	0.2569	0.017*
C3	0.4149 (3)	0.7907 (3)	−0.1920 (2)	0.0138 (5)
H3	0.5247	0.8183	−0.2269	0.017*
C16	0.2281 (3)	1.4120 (3)	0.4680 (2)	0.0165 (5)
H16	0.3142	1.5054	0.4963	0.020*
C4	0.3054 (3)	0.6445 (3)	−0.2101 (2)	0.0146 (5)
H4	0.3426	0.5726	−0.2555	0.018*
C15	0.0780 (4)	1.3594 (3)	0.5286 (2)	0.0184 (5)
H15	0.0604	1.4177	0.5976	0.022*

	U11	U22	U33	U12	U13	U23
Mn1	0.0089 (2)	0.0085 (2)	0.0068 (2)	0.00102 (14)	0.00293 (13)	0.00013 (14)
Cl1	0.0154 (3)	0.0175 (3)	0.0120 (3)	0.0072 (2)	0.0016 (2)	0.0030 (2)
O1	0.0127 (8)	0.0106 (8)	0.0091 (8)	0.0036 (6)	0.0037 (6)	0.0006 (6)
O2	0.0130 (8)	0.0121 (8)	0.0087 (8)	0.0018 (6)	0.0039 (6)	0.0004 (6)
N1	0.0095 (9)	0.0113 (9)	0.0110 (10)	0.0017 (7)	0.0032 (7)	0.0036 (8)
N2	0.0104 (9)	0.0115 (9)	0.0110 (10)	0.0028 (8)	0.0027 (7)	0.0031 (8)
C18	0.0136 (11)	0.0143 (11)	0.0085 (11)	0.0074 (9)	0.0005 (9)	0.0026 (9)
C12	0.0108 (11)	0.0160 (11)	0.0078 (11)	0.0072 (9)	0.0015 (8)	0.0042 (9)
C5	0.0182 (12)	0.0103 (11)	0.0109 (11)	0.0027 (9)	0.0004 (9)	0.0008 (9)
C7	0.0159 (12)	0.0108 (11)	0.0068 (11)	0.0040 (9)	−0.0004 (9)	0.0029 (9)
C8	0.0142 (12)	0.0132 (11)	0.0129 (12)	0.0017 (9)	0.0029 (9)	0.0004 (9)
C2	0.0119 (11)	0.0135 (11)	0.0089 (11)	0.0027 (9)	−0.0011 (9)	0.0021 (9)
C1	0.0121 (11)	0.0128 (11)	0.0061 (10)	0.0052 (9)	−0.0004 (8)	0.0011 (9)
C11	0.0154 (12)	0.0188 (12)	0.0129 (12)	0.0037 (10)	0.0059 (9)	0.0014 (10)
C9	0.0094 (11)	0.0138 (11)	0.0154 (12)	0.0012 (9)	0.0037 (9)	0.0011 (9)
C13	0.0139 (12)	0.0150 (11)	0.0087 (11)	0.0056 (9)	0.0014 (9)	0.0015 (9)
C14	0.0166 (12)	0.0207 (12)	0.0108 (12)	0.0064 (10)	0.0044 (9)	0.0023 (10)
C6	0.0117 (11)	0.0136 (11)	0.0062 (10)	0.0041 (9)	−0.0009 (8)	0.0015 (9)
C17	0.0143 (12)	0.0150 (11)	0.0121 (11)	0.0029 (9)	0.0028 (9)	0.0029 (9)
C10	0.0119 (11)	0.0134 (11)	0.0148 (12)	0.0005 (9)	0.0057 (9)	0.0039 (9)
C3	0.0117 (11)	0.0199 (12)	0.0096 (11)	0.0049 (9)	0.0027 (9)	0.0009 (9)
C16	0.0194 (13)	0.0137 (11)	0.0135 (12)	0.0028 (10)	0.0005 (9)	−0.0010 (10)
C4	0.0169 (12)	0.0154 (12)	0.0123 (12)	0.0078 (10)	0.0021 (9)	−0.0021 (9)
C15	0.0242 (13)	0.0196 (13)	0.0117 (12)	0.0089 (11)	0.0035 (10)	−0.0021 (10)

Mn1—O2	1.8738 (16)	C8—H8C	0.9800
Mn1—O1	1.9191 (16)	C2—C3	1.385 (3)
Mn1—N1	1.9964 (19)	C2—C1	1.400 (3)
Mn1—N2	2.0129 (19)	C2—H2	0.9500
Mn1—Cl1	2.4633 (6)	C1—C6	1.423 (3)
Mn1—O1i	2.4720 (16)	C11—H11A	0.9800
O1—C1	1.348 (3)	C11—H11B	0.9800
O1—Mn1i	2.4720 (16)	C11—H11C	0.9800
O2—C18	1.321 (3)	C9—C10	1.517 (3)
N1—C7	1.302 (3)	C9—H9A	0.9900
N1—C9	1.469 (3)	C9—H9B	0.9900
N2—C12	1.305 (3)	C13—C14	1.422 (3)
N2—C10	1.483 (3)	C14—C15	1.378 (4)
C18—C17	1.413 (3)	C14—H14	0.9500
C18—C13	1.424 (3)	C17—C16	1.382 (3)
C12—C13	1.471 (3)	C17—H17	0.9500
C12—C11	1.513 (3)	C10—H10A	0.9900
C5—C4	1.379 (4)	C10—H10B	0.9900
C5—C6	1.418 (3)	C3—C4	1.402 (3)
C5—H5	0.9500	C3—H3	0.9500
C7—C6	1.467 (3)	C16—C15	1.398 (4)
C7—C8	1.510 (3)	C16—H16	0.9500
C8—H8A	0.9800	C4—H4	0.9500
C8—H8B	0.9800	C15—H15	0.9500
O2—Mn1—O1	95.14 (7)	O1—C1—C2	118.2 (2)
O2—Mn1—N1	170.58 (8)	O1—C1—C6	122.4 (2)
O1—Mn1—N1	87.86 (7)	C2—C1—C6	119.3 (2)
O2—Mn1—N2	90.36 (7)	C12—C11—H11A	109.5
O1—Mn1—N2	163.69 (8)	C12—C11—H11B	109.5
N1—Mn1—N2	84.44 (8)	H11A—C11—H11B	109.5
O2—Mn1—Cl1	95.48 (5)	C12—C11—H11C	109.5
O1—Mn1—Cl1	96.66 (5)	H11A—C11—H11C	109.5
N1—Mn1—Cl1	93.03 (6)	H11B—C11—H11C	109.5
N2—Mn1—Cl1	98.09 (6)	N1—C9—C10	109.25 (19)
O2—Mn1—O1i	88.58 (6)	N1—C9—H9A	109.8
O1—Mn1—O1i	77.02 (7)	C10—C9—H9A	109.8
N1—Mn1—O1i	83.39 (7)	N1—C9—H9B	109.8
N2—Mn1—O1i	87.80 (7)	C10—C9—H9B	109.8
Cl1—Mn1—O1i	172.81 (4)	H9A—C9—H9B	108.3
C1—O1—Mn1	121.87 (14)	C14—C13—C18	117.7 (2)
C1—O1—Mn1i	112.89 (13)	C14—C13—C12	119.4 (2)
Mn1—O1—Mn1i	102.98 (7)	C18—C13—C12	122.9 (2)
C18—O2—Mn1	130.34 (15)	C15—C14—C13	122.2 (2)
C7—N1—C9	121.6 (2)	C15—C14—H14	118.9
C7—N1—Mn1	127.36 (16)	C13—C14—H14	118.9
C9—N1—Mn1	110.67 (14)	C5—C6—C1	118.3 (2)
C12—N2—C10	119.38 (19)	C5—C6—C7	119.8 (2)
C12—N2—Mn1	129.33 (16)	C1—C6—C7	121.7 (2)
C10—N2—Mn1	111.08 (14)	C16—C17—C18	122.1 (2)
O2—C18—C17	116.5 (2)	C16—C17—H17	118.9
O2—C18—C13	125.0 (2)	C18—C17—H17	118.9
C17—C18—C13	118.5 (2)	N2—C10—C9	109.88 (18)
N2—C12—C13	121.5 (2)	N2—C10—H10A	109.7
N2—C12—C11	119.1 (2)	C9—C10—H10A	109.7
C13—C12—C11	119.4 (2)	N2—C10—H10B	109.7
C4—C5—C6	121.3 (2)	C9—C10—H10B	109.7
C4—C5—H5	119.4	H10A—C10—H10B	108.2
C6—C5—H5	119.4	C2—C3—C4	119.9 (2)
N1—C7—C6	120.7 (2)	C2—C3—H3	120.1
N1—C7—C8	119.9 (2)	C4—C3—H3	120.1
C6—C7—C8	119.4 (2)	C17—C16—C15	119.4 (2)
C7—C8—H8A	109.5	C17—C16—H16	120.3
C7—C8—H8B	109.5	C15—C16—H16	120.3
H8A—C8—H8B	109.5	C5—C4—C3	119.9 (2)
C7—C8—H8C	109.5	C5—C4—H4	120.0
H8A—C8—H8C	109.5	C3—C4—H4	120.0
H8B—C8—H8C	109.5	C14—C15—C16	119.8 (2)
C3—C2—C1	121.3 (2)	C14—C15—H15	120.1
C3—C2—H2	119.4	C16—C15—H15	120.1
C1—C2—H2	119.4
O2—Mn1—O1—C1	144.83 (16)	Mn1—N1—C7—C8	−176.24 (16)
N1—Mn1—O1—C1	−44.12 (17)	Mn1—O1—C1—C2	−145.77 (17)
N2—Mn1—O1—C1	−105.9 (3)	Mn1i—O1—C1—C2	90.9 (2)
Cl1—Mn1—O1—C1	48.69 (16)	Mn1—O1—C1—C6	37.8 (3)
O1i—Mn1—O1—C1	−127.83 (18)	Mn1i—O1—C1—C6	−85.5 (2)
O2—Mn1—O1—Mn1i	−87.35 (7)	C3—C2—C1—O1	−178.2 (2)
N1—Mn1—O1—Mn1i	83.71 (7)	C3—C2—C1—C6	−1.7 (3)
N2—Mn1—O1—Mn1i	21.9 (3)	C7—N1—C9—C10	149.6 (2)
Cl1—Mn1—O1—Mn1i	176.51 (4)	Mn1—N1—C9—C10	−36.7 (2)
O1i—Mn1—O1—Mn1i	0.0	O2—C18—C13—C14	−175.6 (2)
O1—Mn1—O2—C18	172.36 (19)	C17—C18—C13—C14	4.1 (3)
N2—Mn1—O2—C18	7.7 (2)	O2—C18—C13—C12	3.3 (4)
Cl1—Mn1—O2—C18	−90.43 (19)	C17—C18—C13—C12	−177.0 (2)
O1i—Mn1—O2—C18	95.52 (19)	N2—C12—C13—C14	176.1 (2)
O1—Mn1—N1—C7	25.1 (2)	C11—C12—C13—C14	−3.6 (3)
N2—Mn1—N1—C7	−169.3 (2)	N2—C12—C13—C18	−2.9 (3)
Cl1—Mn1—N1—C7	−71.4 (2)	C11—C12—C13—C18	177.4 (2)
O1i—Mn1—N1—C7	102.3 (2)	C18—C13—C14—C15	−1.2 (4)
O1—Mn1—N1—C9	−148.16 (15)	C12—C13—C14—C15	179.8 (2)
N2—Mn1—N1—C9	17.44 (15)	C4—C5—C6—C1	0.1 (3)
Cl1—Mn1—N1—C9	115.28 (14)	C4—C5—C6—C7	175.1 (2)
O1i—Mn1—N1—C9	−70.98 (15)	O1—C1—C6—C5	178.0 (2)
O2—Mn1—N2—C12	−7.3 (2)	C2—C1—C6—C5	1.6 (3)
O1—Mn1—N2—C12	−117.2 (3)	O1—C1—C6—C7	3.1 (3)
N1—Mn1—N2—C12	−179.4 (2)	C2—C1—C6—C7	−173.3 (2)
Cl1—Mn1—N2—C12	88.3 (2)	N1—C7—C6—C5	161.2 (2)
O1i—Mn1—N2—C12	−95.9 (2)	C8—C7—C6—C5	−20.0 (3)
O2—Mn1—N2—C10	178.04 (15)	N1—C7—C6—C1	−24.0 (3)
O1—Mn1—N2—C10	68.1 (3)	C8—C7—C6—C1	154.8 (2)
N1—Mn1—N2—C10	5.90 (15)	O2—C18—C17—C16	175.2 (2)
Cl1—Mn1—N2—C10	−86.38 (15)	C13—C18—C17—C16	−4.5 (4)
O1i—Mn1—N2—C10	89.48 (15)	C12—N2—C10—C9	157.5 (2)
Mn1—O2—C18—C17	172.84 (15)	Mn1—N2—C10—C9	−27.3 (2)
Mn1—O2—C18—C13	−7.4 (3)	N1—C9—C10—N2	41.7 (3)
C10—N2—C12—C13	−179.6 (2)	C1—C2—C3—C4	−0.1 (4)
Mn1—N2—C12—C13	6.2 (3)	C18—C17—C16—C15	1.8 (4)
C10—N2—C12—C11	0.2 (3)	C6—C5—C4—C3	−1.9 (4)
Mn1—N2—C12—C11	−174.11 (16)	C2—C3—C4—C5	1.9 (4)
C9—N1—C7—C6	175.2 (2)	C13—C14—C15—C16	−1.5 (4)
Mn1—N1—C7—C6	2.5 (3)	C17—C16—C15—C14	1.2 (4)
C9—N1—C7—C8	−3.6 (3)

Mn1—O2	1.8738 (16)
Mn1—O1	1.9191 (16)
Mn1—N1	1.9964 (19)
Mn1—N2	2.0129 (19)
Mn1—Cl1	2.4633 (6)
Mn1—O1i	2.4720 (16)

O2—Mn1—O1	95.14 (7)
O2—Mn1—N1	170.58 (8)
O1—Mn1—N1	87.86 (7)
O2—Mn1—N2	90.36 (7)
O1—Mn1—N2	163.69 (8)
N1—Mn1—N2	84.44 (8)
O2—Mn1—Cl1	95.48 (5)
O1—Mn1—Cl1	96.66 (5)
N1—Mn1—Cl1	93.03 (6)
N2—Mn1—Cl1	98.09 (6)
O2—Mn1—O1i	88.58 (6)
O1—Mn1—O1i	77.02 (7)
N1—Mn1—O1i	83.39 (7)
N2—Mn1—O1i	87.80 (7)
Cl1—Mn1—O1i	172.81 (4)
Mn1—O1—Mn1i	102.98 (7)

Symmetry code: (i) .