(Croconato-κO,O')bis-(1,10-phenanthroline-κN,N')manganese(II).

The title complex, [Mn(C(5)O(5))(C(12)H(8)N(2))(2)], lies across a crystallographic twofold axis which passes through the Mn atom and bisects the croconate ligand. The two 1,10-phenanthroline (phen) ligands are arranged in a propeller manner and the local mol-ecular geometry of the MnN(4)O(2) unit is severely distorted octa-hedral. This may be inter-preted as a structural perturbation of the MnN(4) square by the croconate ligand. In the crystal structure, the dipole moments of the mol-ecules are arranged alternately along the +b and -b directions. All the phen ligands are involved in π stacking inter-actions, alternately along the [110] and [10] directions. The alternate spacings between the neighbouring phen planes in the one-dimensional π stacks are 3.361 (2) and 3.526 (2) Å.

Related literature

For related literature, see: Chen et al. (2005 ▶, 2007 ▶); Coronado et al. (2007 ▶); Maji et al. (2003 ▶); Sletten et al. (1998 ▶); Wang et al. (2002 ▶).

Experimental

Crystal data

[Mn(C5O5)(C12H8N2)2]

M = 555.40

Monoclinic,

a = 14.9185 (6) Å

b = 10.3749 (4) Å

c = 16.0859 (6) Å

β = 109.885 (1)°

V = 2341.30 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.62 mm−1

T = 120 (2) K

0.44 × 0.33 × 0.22 mm

Data collection

Siemens SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.617, T max = 0.746 (expected range = 0.722–0.873)

16256 measured reflections

3356 independent reflections

3214 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.081

S = 1.06

3356 reflections

210 parameters

All H-atom parameters refined

Δρmax = 0.50 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1997 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065841/fj2088sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065841/fj2088Isup2.hkl

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

[Mn(C5O5)(C12H8N2)2]	F000 = 1132
Mr = 555.40	Dx = 1.576 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6761 reflections
a = 14.9185 (6) Å	θ = 2.4–30.0º
b = 10.3749 (4) Å	µ = 0.62 mm−1
c = 16.0859 (6) Å	T = 120 (2) K
β = 109.885 (1)º	Parallelepiped, green
V = 2341.30 (16) Å3	0.44 × 0.33 × 0.22 mm
Z = 4

Siemens SMART 1K CCD area-detector diffractometer	3356 independent reflections
Radiation source: fine-focus sealed tube	3214 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
Detector resolution: 8 pixels mm-1	θmax = 30.0º
T = 120(2) K	θmin = 2.4º
φ and ω scans	h = −20→20
Absorption correction: multi-scan(SADABS; Bruker, 2006)	k = −14→14
Tmin = 0.617, Tmax = 0.746	l = −22→22
16256 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026	All H-atom parameters refined
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.0494P)2 + 1.5339P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
3356 reflections	Δρmax = 0.50 e Å−3
210 parameters	Δρmin = −0.22 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Mn1	0.5000	0.26400 (2)	0.2500	0.01622 (7)
O1	0.59885 (5)	0.43062 (7)	0.28042 (5)	0.02103 (16)
O2	0.67021 (6)	0.70377 (9)	0.30364 (6)	0.02748 (18)
O3	0.5000	0.87022 (11)	0.2500	0.0219 (2)
N1	0.62594 (6)	0.15684 (8)	0.34684 (6)	0.01795 (16)
N2	0.46304 (6)	0.23245 (8)	0.37113 (6)	0.01674 (17)
C1	0.70739 (7)	0.12417 (11)	0.33554 (7)	0.0215 (2)
H1	0.7115 (10)	0.1353 (15)	0.2787 (10)	0.025 (4)*
C2	0.78638 (8)	0.07591 (11)	0.40428 (8)	0.0236 (2)
H2	0.8456 (12)	0.0555 (17)	0.3931 (11)	0.035 (4)*
C3	0.78032 (7)	0.05937 (10)	0.48675 (8)	0.0216 (2)
H3	0.8314 (10)	0.0290 (15)	0.5356 (10)	0.023 (3)*
C10	0.69459 (7)	0.09129 (10)	0.50113 (7)	0.01780 (18)
C9	0.61971 (7)	0.14089 (9)	0.42867 (6)	0.01610 (18)
C11	0.53204 (6)	0.17845 (9)	0.44123 (6)	0.01574 (18)
C12	0.52078 (7)	0.15896 (10)	0.52374 (6)	0.01709 (18)
C5	0.59808 (7)	0.10556 (10)	0.59570 (7)	0.01991 (19)
H5	0.5877 (11)	0.0922 (15)	0.6492 (11)	0.030 (4)*
C4	0.68188 (7)	0.07441 (10)	0.58486 (7)	0.02041 (19)
H4	0.7324 (11)	0.0420 (15)	0.6319 (10)	0.023 (3)*
C6	0.43206 (7)	0.19283 (10)	0.53119 (7)	0.01892 (19)
H6	0.4204 (11)	0.1750 (15)	0.5844 (11)	0.027 (4)*
C7	0.36277 (8)	0.24697 (10)	0.45998 (7)	0.0194 (2)
H7	0.3036 (12)	0.2722 (14)	0.4624 (11)	0.025 (4)*
C8	0.38134 (7)	0.26697 (10)	0.38121 (7)	0.01831 (19)
H8	0.3372 (10)	0.3074 (14)	0.3314 (10)	0.020 (3)*
C13	0.55136 (6)	0.53447 (10)	0.26577 (6)	0.01663 (18)
C14	0.58663 (7)	0.66724 (10)	0.27693 (6)	0.01791 (18)
C15	0.5000	0.75179 (14)	0.2500	0.0172 (3)

	U11	U22	U33	U12	U13	U23
Mn1	0.01278 (11)	0.02053 (12)	0.01434 (11)	0.000	0.00330 (8)	0.000
O1	0.0128 (3)	0.0224 (4)	0.0243 (4)	0.0014 (3)	0.0017 (3)	−0.0019 (3)
O2	0.0147 (3)	0.0294 (4)	0.0350 (4)	−0.0044 (3)	0.0041 (3)	−0.0040 (3)
O3	0.0248 (5)	0.0215 (5)	0.0198 (5)	0.000	0.0083 (4)	0.000
N1	0.0156 (4)	0.0193 (4)	0.0190 (4)	0.0014 (3)	0.0061 (3)	0.0006 (3)
N2	0.0132 (4)	0.0201 (4)	0.0156 (4)	0.0011 (3)	0.0031 (3)	0.0006 (3)
C1	0.0192 (5)	0.0234 (5)	0.0236 (5)	0.0032 (4)	0.0094 (4)	0.0018 (4)
C2	0.0167 (4)	0.0249 (5)	0.0301 (5)	0.0047 (4)	0.0090 (4)	0.0017 (4)
C3	0.0147 (4)	0.0218 (5)	0.0256 (5)	0.0033 (3)	0.0034 (4)	0.0011 (4)
C10	0.0144 (4)	0.0173 (4)	0.0193 (4)	0.0003 (3)	0.0025 (3)	−0.0004 (3)
C9	0.0136 (4)	0.0160 (4)	0.0175 (4)	−0.0001 (3)	0.0037 (3)	−0.0007 (3)
C11	0.0130 (4)	0.0167 (4)	0.0160 (4)	−0.0004 (3)	0.0030 (3)	−0.0010 (3)
C12	0.0155 (4)	0.0186 (4)	0.0155 (4)	−0.0010 (3)	0.0032 (3)	−0.0021 (3)
C5	0.0198 (4)	0.0228 (5)	0.0147 (4)	0.0001 (4)	0.0027 (3)	−0.0005 (3)
C4	0.0174 (4)	0.0219 (5)	0.0176 (4)	0.0012 (3)	0.0003 (3)	0.0003 (3)
C6	0.0179 (4)	0.0228 (5)	0.0161 (4)	−0.0019 (4)	0.0060 (3)	−0.0030 (4)
C7	0.0150 (4)	0.0239 (5)	0.0196 (5)	0.0005 (3)	0.0064 (4)	−0.0022 (3)
C8	0.0138 (4)	0.0220 (5)	0.0181 (5)	0.0012 (3)	0.0040 (3)	0.0002 (3)
C13	0.0119 (4)	0.0230 (4)	0.0134 (4)	−0.0001 (3)	0.0023 (3)	−0.0011 (3)
C14	0.0139 (4)	0.0232 (5)	0.0157 (4)	−0.0009 (3)	0.0040 (3)	−0.0018 (3)
C15	0.0150 (6)	0.0234 (6)	0.0130 (6)	0.000	0.0046 (5)	0.000

Mn1—O1	2.2163 (8)	C10—C9	1.4091 (13)
Mn1—O1i	2.2163 (8)	C10—C4	1.4333 (15)
Mn1—N2	2.2222 (9)	C9—C11	1.4433 (13)
Mn1—N2i	2.2222 (9)	C11—C12	1.4080 (13)
Mn1—N1i	2.2807 (9)	C12—C6	1.4134 (13)
Mn1—N1	2.2807 (9)	C12—C5	1.4383 (13)
O1—C13	1.2668 (12)	C5—C4	1.3587 (15)
O2—C14	1.2323 (12)	C5—H5	0.934 (17)
O3—C15	1.2287 (18)	C4—H4	0.931 (15)
N1—C1	1.3322 (13)	C6—C7	1.3750 (15)
N1—C9	1.3607 (13)	C6—H6	0.947 (16)
N2—C8	1.3321 (13)	C7—C8	1.4015 (15)
N2—C11	1.3621 (12)	C7—H7	0.934 (17)
C1—C2	1.4055 (15)	C8—H8	0.945 (14)
C1—H1	0.944 (16)	C13—C13i	1.4412 (18)
C2—C3	1.3709 (16)	C13—C14	1.4637 (14)
C2—H2	0.982 (17)	C14—C15	1.4989 (13)
C3—C10	1.4143 (14)	C15—C14i	1.4989 (13)
C3—H3	0.943 (15)
O1—Mn1—O1i	77.48 (4)	N1—C9—C10	123.29 (9)
O1—Mn1—N2	105.44 (3)	N1—C9—C11	117.77 (8)
O1i—Mn1—N2	87.91 (3)	C10—C9—C11	118.94 (9)
O1—Mn1—N2i	87.91 (3)	N2—C11—C12	122.72 (9)
O1i—Mn1—N2i	105.44 (3)	N2—C11—C9	117.44 (9)
N2—Mn1—N2i	163.06 (5)	C12—C11—C9	119.84 (8)
O1—Mn1—N1i	149.62 (3)	C11—C12—C6	117.37 (9)
O1i—Mn1—N1i	84.13 (3)	C11—C12—C5	119.60 (9)
N2—Mn1—N1i	97.74 (3)	C6—C12—C5	123.03 (9)
N2i—Mn1—N1i	73.85 (3)	C4—C5—C12	120.61 (9)
O1—Mn1—N1	84.13 (3)	C4—C5—H5	122.0 (10)
O1i—Mn1—N1	149.62 (3)	C12—C5—H5	117.3 (10)
N2—Mn1—N1	73.85 (3)	C5—C4—C10	120.87 (9)
N2i—Mn1—N1	97.74 (3)	C5—C4—H4	120.5 (9)
N1i—Mn1—N1	121.66 (5)	C10—C4—H4	118.6 (9)
C13—O1—Mn1	109.53 (6)	C7—C6—C12	119.42 (9)
C1—N1—C9	117.82 (9)	C7—C6—H6	121.0 (9)
C1—N1—Mn1	127.48 (7)	C12—C6—H6	119.5 (9)
C9—N1—Mn1	114.11 (6)	C6—C7—C8	119.34 (10)
C8—N2—C11	118.35 (9)	C6—C7—H7	122.2 (10)
C8—N2—Mn1	125.26 (7)	C8—C7—H7	118.5 (10)
C11—N2—Mn1	116.32 (7)	N2—C8—C7	122.73 (10)
N1—C1—C2	122.87 (10)	N2—C8—H8	114.7 (9)
N1—C1—H1	117.6 (9)	C7—C8—H8	122.5 (9)
C2—C1—H1	119.5 (9)	O1—C13—C13i	121.73 (5)
C3—C2—C1	119.50 (10)	O1—C13—C14	128.51 (8)
C3—C2—H2	120.6 (10)	C13i—C13—C14	109.76 (5)
C1—C2—H2	119.9 (10)	O2—C14—C13	127.67 (10)
C2—C3—C10	119.33 (9)	O2—C14—C15	126.27 (10)
C2—C3—H3	123.1 (9)	C13—C14—C15	106.06 (8)
C10—C3—H3	117.5 (9)	O3—C15—C14i	125.82 (6)
C9—C10—C3	117.18 (9)	O3—C15—C14	125.82 (6)
C9—C10—C4	120.06 (9)	C14i—C15—C14	108.36 (12)
C3—C10—C4	122.76 (9)