Bis(benzoato-κ2O,O′)(2,9-dimethyl-1,10-phenanthroline-κ2N,N′)manganese(II)

Zhao, P.-Z.; Xuan, X.-P.; Wang, J.-G.

doi:10.1107/S1600536807033302

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Bis(benzoato-κ²O,O′)(2,9-dimethyl-1,10-phenanthroline-κ²N,N′)manganese(II)

P.-Z. Zhao, X.-P. Xuan and J.-G. Wang

In the title compound, [Mn(C₇H₅O₂)₂(C₁₄H₁₂N₂)], the Mn^II ion is located on a twofold rotation axis and is coordinated by a bidentate 2,9-dimethyl-1,10-phenanthroline ligand and two bidentate benzoate anions in a distorted octahedral environment. The phenyl ring is disordered over two positions, with site occupancy factors of ca 0.57 and 0.43. The crystal packing is stabilized by π–π interactions between the 2,9-dimethyl-1,10-phenanthroline rings of neighboring molecules, with a distance between their ring planes of 3.443 Å.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033302/hg2237sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033302/hg2237Isup2.hkl Contains datablock I

CCDC reference: 657569

checkCIF report

Key indicators

Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R factor = 0.033
wR factor = 0.094
Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT301_ALERT_3_B Main Residue  Disorder .........................      26.00 Perc.
PLAT432_ALERT_2_B Short Inter X...Y Contact  C13'   ..  C13'    ..       3.03 Ang.

Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       8.40 Deg.
              C8'  -C14  -C8      1.555   1.555   1.555

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         93

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

It is general believed that manganese plays an important role in biological systems (Ruttingter & Dismukes, 1997). In addition, metal-phenanthroline complexes and their derivatives have attracted much attention because of their peculiar features (Wang et al., 1996; Wall et al., 1999; Naing et al., 1995). The title complex, (I), was recently obtained from the reaction of 2,9-dimethyl-1,10-phenanthroline, sodium benzoate and Mn(NO₃)₂ in an ethanol/water mixture. Here we report its structure.

Each Mn^II ion is located on a twofold symmetry axis and is six-coordinated by two N atoms from a 2,9-dimethyl-1,10-phenanthroline ligand, and four O atoms from two benzoate anions. The MnO₄N₂ unit forms a distorted octahedron geometry, with two O atoms occupying the axial positions with the axial O—Mn—O angle 168.60 (7)° (Fig.1). The Mn—N bond length is 2.2360 (13)Å and the Mn—O bond lengths are 2.1611 (13) and 2.2971 (14)Å respectively

In the crystal structure, molecules are linked into a one dimensional network by π-π interactions between the 2,9-dimethyl-1,10-phenanthroline ring systems (Fig. 2). These intermolecular interactions occur between the parallel rings within offset face-to-face packing. The distance of neighboring molecules parallel ring planes is 3.4432 Å.

Related literature top

For related literature, see: Wang et al. (1996); Wall et al. (1999); Naing et al. (1995); Xuan et al. (2007).

For related literature, see: Ruttingter & Dismukes (1997).

Experimental top

To a solution of 2,9-dimethyl-1,10-phenanthroline hemihydrate (C₁₄H₁₂N₂0.5H₂O, 0.109 g, 0.5 mmol) in ethanol(10 ml) and sodium benzoate (0.073 g, 0.5 mmol) in 1:1 (v/v) ethanol/water (20 ml) was added a 0.205 g 50% solution of Mn(NO₃)₂ (0.089 g, 0.5 mmol) in distilled water(5 ml). The mixture solution was stirred and refluxed for 4 h at 333 K. The hot solution was then filtered into a bottle. Yellow single crystals of (I) were appeared over a period of one week by slow evaporation at room temperature.

Structure description top

For related literature, see: Wang et al. (1996); Wall et al. (1999); Naing et al. (1995); Xuan et al. (2007).

For related literature, see: Ruttingter & Dismukes (1997).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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.

Figures top

	Fig. 1. The molecular stucture of the title complex(I),with atome labels and 30% probability displacement ellipsoids for non-H atoms. Symmetry code for the symbol 'A': -x + 2, y, -z + 1/2
	Fig. 2. The π-π interaction between 2,9-dimethyl-1,10-phenanthroline ligands in the crystal structure of (I). H atoms have been omitted for clarity.

Bis(benzoato-κ²O,O')(2,9-dimethyl-1,10-phenanthroline-\k²N,N')manganese(II) top

Crystal data top

[Mn(C₇H₅O₂)₂(C₁₄H₁₂N₂)]	F(000) = 1044
M_r = 505.42	D_x = 1.378 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3415 reflections
a = 17.7020 (19) Å	θ = 2.3–26.5°
b = 14.3903 (16) Å	µ = 0.58 mm⁻¹
c = 9.5678 (11) Å	T = 291 K
β = 91.431 (1)°	Block, yellow
V = 2436.5 (5) Å³	0.43 × 0.24 × 0.21 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2274 independent reflections
Radiation source: fine-focus sealed tube	1940 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
φ and ω scans	θ_max = 25.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −20→21
T_min = 0.789, T_max = 0.886	k = −17→17
9141 measured reflections	l = −11→11

Refinement top

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0453P)² + 1.3028P] where P = (F_o² + 2F_c²)/3
2274 reflections	(Δ/σ)_max = 0.002
179 parameters	Δρ_max = 0.25 e Å⁻³
93 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Mn(C₇H₅O₂)₂(C₁₄H₁₂N₂)]	V = 2436.5 (5) Å³
M_r = 505.42	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 17.7020 (19) Å	µ = 0.58 mm⁻¹
b = 14.3903 (16) Å	T = 291 K
c = 9.5678 (11) Å	0.43 × 0.24 × 0.21 mm
β = 91.431 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2274 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	1940 reflections with I > 2σ(I)
T_min = 0.789, T_max = 0.886	R_int = 0.020
9141 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	93 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.06	Δρ_max = 0.25 e Å⁻³
2274 reflections	Δρ_min = −0.30 e Å⁻³
179 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C8	0.87920 (18)	0.1290 (2)	0.5538 (3)	0.0514 (5)	0.567 (2)
C9	0.8162 (2)	0.1670 (3)	0.6115 (3)	0.0608 (6)	0.567 (2)
H9	0.7996	0.2253	0.5820	0.073*	0.567 (2)
C10	0.7767 (2)	0.1203 (3)	0.7128 (4)	0.0759 (6)	0.567 (2)
H10	0.7341	0.1469	0.7512	0.091*	0.567 (2)
C11	0.8011 (2)	0.0343 (3)	0.7557 (4)	0.0850 (11)	0.567 (2)
H11	0.7748	0.0023	0.8235	0.102*	0.567 (2)
C12	0.8638 (2)	−0.0046 (3)	0.7000 (4)	0.0937 (11)	0.567 (2)
H12	0.8802	−0.0628	0.7302	0.112*	0.567 (2)
C13	0.9028 (2)	0.0422 (3)	0.5988 (4)	0.0749 (9)	0.567 (2)
H13	0.9453	0.0152	0.5606	0.090*	0.567 (2)
C8'	0.8885 (3)	0.1355 (2)	0.5663 (4)	0.0514 (5)	0.433 (2)
C9'	0.8128 (3)	0.1519 (3)	0.5892 (6)	0.0608 (6)	0.433 (2)
H9'	0.7848	0.1894	0.5280	0.073*	0.433 (2)
C10'	0.7790 (3)	0.1121 (4)	0.7040 (6)	0.0759 (6)	0.433 (2)
H10'	0.7281	0.1230	0.7196	0.091*	0.433 (2)
C11'	0.8198 (3)	0.0572 (4)	0.7940 (6)	0.0850 (11)	0.433 (2)
H11'	0.7968	0.0309	0.8709	0.102*	0.433 (2)
C12'	0.8948 (3)	0.0407 (4)	0.7712 (5)	0.0937 (11)	0.433 (2)
H12'	0.9224	0.0028	0.8325	0.112*	0.433 (2)
C13'	0.9296 (3)	0.0801 (3)	0.6571 (5)	0.0749 (9)	0.433 (2)
H13'	0.9806	0.0690	0.6422	0.090*	0.433 (2)
Mn1	1.0000	0.25641 (2)	0.2500	0.05121 (11)
O1	0.99102 (8)	0.15840 (10)	0.41993 (15)	0.0780 (4)
O2	0.89099 (8)	0.24055 (9)	0.37312 (15)	0.0713 (4)
N1	0.94460 (7)	0.37936 (9)	0.14787 (12)	0.0455 (3)
C1	0.88955 (9)	0.37836 (13)	0.04959 (17)	0.0539 (4)
C2	0.86000 (10)	0.46112 (15)	−0.00559 (18)	0.0633 (5)
H2	0.8220	0.4588	−0.0744	0.076*
C3	0.88607 (11)	0.54461 (14)	0.04000 (18)	0.0614 (5)
H3	0.8664	0.5992	0.0020	0.074*
C4	0.94303 (10)	0.54831 (12)	0.14496 (16)	0.0518 (4)
C5	0.97064 (9)	0.46279 (11)	0.19584 (14)	0.0434 (4)
C6	0.97268 (11)	0.63307 (12)	0.19948 (18)	0.0636 (5)
H6	0.9542	0.6893	0.1651	0.076*
C7	0.86054 (12)	0.28554 (16)	0.0018 (2)	0.0756 (6)
H7A	0.9015	0.2496	−0.0339	0.113*
H7B	0.8226	0.2941	−0.0705	0.113*
H7C	0.8390	0.2535	0.0792	0.113*
C14	0.92396 (11)	0.17951 (11)	0.44429 (17)	0.0541 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C8	0.0568 (11)	0.0505 (10)	0.0472 (9)	0.0018 (8)	0.0059 (8)	0.0010 (8)
C9	0.0614 (11)	0.0606 (14)	0.0605 (14)	0.0018 (10)	0.0022 (10)	−0.0056 (11)
C10	0.0597 (11)	0.0969 (16)	0.0718 (13)	−0.0051 (11)	0.0176 (10)	−0.0054 (12)
C11	0.077 (2)	0.111 (2)	0.068 (2)	−0.0111 (18)	0.0173 (16)	0.0230 (18)
C12	0.091 (2)	0.102 (2)	0.089 (2)	0.0151 (19)	0.0176 (18)	0.0505 (18)
C13	0.0684 (18)	0.079 (2)	0.078 (2)	0.0173 (15)	0.0184 (15)	0.0289 (16)
C8'	0.0568 (11)	0.0505 (10)	0.0472 (9)	0.0018 (8)	0.0059 (8)	0.0010 (8)
C9'	0.0614 (11)	0.0606 (14)	0.0605 (14)	0.0018 (10)	0.0022 (10)	−0.0056 (11)
C10'	0.0597 (11)	0.0969 (16)	0.0718 (13)	−0.0051 (11)	0.0176 (10)	−0.0054 (12)
C11'	0.077 (2)	0.111 (2)	0.068 (2)	−0.0111 (18)	0.0173 (16)	0.0230 (18)
C12'	0.091 (2)	0.102 (2)	0.089 (2)	0.0151 (19)	0.0176 (18)	0.0505 (18)
C13'	0.0684 (18)	0.079 (2)	0.078 (2)	0.0173 (15)	0.0184 (15)	0.0289 (16)
Mn1	0.0594 (2)	0.0447 (2)	0.0499 (2)	0.000	0.00940 (16)	0.000
O1	0.0753 (8)	0.0800 (9)	0.0799 (9)	0.0175 (7)	0.0294 (7)	0.0247 (7)
O2	0.0771 (9)	0.0648 (8)	0.0726 (8)	0.0061 (6)	0.0113 (7)	0.0217 (6)
N1	0.0461 (7)	0.0515 (7)	0.0391 (6)	−0.0034 (6)	0.0057 (5)	0.0023 (5)
C1	0.0464 (9)	0.0705 (11)	0.0450 (8)	−0.0074 (8)	0.0047 (7)	0.0030 (8)
C2	0.0506 (9)	0.0911 (14)	0.0483 (9)	0.0032 (9)	0.0004 (8)	0.0127 (9)
C3	0.0633 (11)	0.0702 (11)	0.0511 (9)	0.0139 (9)	0.0091 (8)	0.0160 (8)
C4	0.0599 (10)	0.0554 (9)	0.0410 (8)	0.0071 (8)	0.0144 (7)	0.0071 (7)
C5	0.0476 (8)	0.0493 (8)	0.0337 (7)	0.0003 (7)	0.0114 (6)	0.0017 (6)
C6	0.0907 (14)	0.0461 (9)	0.0547 (10)	0.0077 (9)	0.0166 (9)	0.0051 (7)
C7	0.0678 (12)	0.0875 (14)	0.0709 (12)	−0.0233 (11)	−0.0113 (10)	−0.0018 (11)
C14	0.0697 (11)	0.0424 (8)	0.0506 (9)	−0.0007 (8)	0.0063 (8)	−0.0035 (7)

Geometric parameters (Å, º) top

C8—C9	1.371 (5)	Mn1—O1	2.1611 (13)
C8—C13	1.383 (5)	Mn1—N1	2.2360 (13)
C8—C14	1.515 (4)	Mn1—N1ⁱ	2.2360 (13)
C9—C10	1.383 (5)	Mn1—O2ⁱ	2.2971 (14)
C9—H9	0.9300	Mn1—O2	2.2972 (14)
C10—C11	1.370 (6)	Mn1—C14ⁱ	2.5723 (17)
C10—H10	0.9300	Mn1—C14	2.5724 (17)
C11—C12	1.363 (6)	O1—C14	1.253 (2)
C11—H11	0.9300	O2—C14	1.247 (2)
C12—C13	1.379 (5)	N1—C1	1.337 (2)
C12—H12	0.9300	N1—C5	1.3616 (19)
C13—H13	0.9300	C1—C2	1.399 (3)
C8'—C13'	1.375 (6)	C1—C7	1.498 (3)
C8'—C9'	1.383 (7)	C2—C3	1.355 (3)
C8'—C14	1.481 (5)	C2—H2	0.9300
C9'—C10'	1.388 (7)	C3—C4	1.406 (2)
C9'—H9'	0.9300	C3—H3	0.9300
C10'—C11'	1.363 (8)	C4—C5	1.407 (2)
C10'—H10'	0.9300	C4—C6	1.422 (2)
C11'—C12'	1.372 (7)	C5—C5ⁱ	1.449 (3)
C11'—H11'	0.9300	C6—C6ⁱ	1.350 (4)
C12'—C13'	1.388 (6)	C6—H6	0.9300
C12'—H12'	0.9300	C7—H7A	0.9600
C13'—H13'	0.9300	C7—H7B	0.9600
Mn1—O1ⁱ	2.1611 (13)	C7—H7C	0.9600

C9—C8—C13	118.5 (3)	O1—Mn1—C14ⁱ	108.21 (5)
C9—C8—C14	122.1 (3)	N1—Mn1—C14ⁱ	104.85 (5)
C13—C8—C14	119.3 (3)	N1ⁱ—Mn1—C14ⁱ	115.12 (5)
C8—C9—C10	121.2 (4)	O2ⁱ—Mn1—C14ⁱ	28.98 (5)
C8—C9—H9	119.4	O2—Mn1—C14ⁱ	142.12 (6)
C10—C9—H9	119.4	O1ⁱ—Mn1—C14	108.21 (5)
C11—C10—C9	119.2 (4)	O1—Mn1—C14	29.07 (5)
C11—C10—H10	120.4	N1—Mn1—C14	115.12 (5)
C9—C10—H10	120.4	N1ⁱ—Mn1—C14	104.85 (5)
C12—C11—C10	120.5 (4)	O2ⁱ—Mn1—C14	142.12 (6)
C12—C11—H11	119.8	O2—Mn1—C14	28.98 (5)
C10—C11—H11	119.8	C14ⁱ—Mn1—C14	129.04 (7)
C11—C12—C13	120.1 (4)	C14—O1—Mn1	93.99 (11)
C11—C12—H12	120.0	C14—O2—Mn1	87.84 (11)
C13—C12—H12	120.0	C1—N1—C5	118.76 (14)
C12—C13—C8	120.5 (3)	C1—N1—Mn1	127.07 (11)
C12—C13—H13	119.8	C5—N1—Mn1	114.16 (10)
C8—C13—H13	119.8	N1—C1—C2	121.02 (16)
C13'—C8'—C9'	119.9 (4)	N1—C1—C7	117.53 (16)
C13'—C8'—C14	121.2 (4)	C2—C1—C7	121.45 (16)
C9'—C8'—C14	118.9 (4)	C3—C2—C1	120.80 (17)
C8'—C9'—C10'	119.6 (5)	C3—C2—H2	119.6
C8'—C9'—H9'	120.2	C1—C2—H2	119.6
C10'—C9'—H9'	120.2	C2—C3—C4	119.73 (17)
C11'—C10'—C9'	120.5 (5)	C2—C3—H3	120.1
C11'—C10'—H10'	119.7	C4—C3—H3	120.1
C9'—C10'—H10'	119.7	C3—C4—C5	116.79 (16)
C10'—C11'—C12'	120.0 (5)	C3—C4—C6	123.10 (16)
C10'—C11'—H11'	120.0	C5—C4—C6	120.11 (15)
C12'—C11'—H11'	120.0	N1—C5—C4	122.88 (14)
C11'—C12'—C13'	120.3 (5)	N1—C5—C5ⁱ	118.15 (8)
C11'—C12'—H12'	119.8	C4—C5—C5ⁱ	118.96 (9)
C13'—C12'—H12'	119.8	C6ⁱ—C6—C4	120.93 (10)
C8'—C13'—C12'	119.7 (4)	C6ⁱ—C6—H6	119.5
C8'—C13'—H13'	120.1	C4—C6—H6	119.5
C12'—C13'—H13'	120.1	C1—C7—H7A	109.5
O1ⁱ—Mn1—O1	98.53 (8)	C1—C7—H7B	109.5
O1ⁱ—Mn1—N1	103.14 (5)	H7A—C7—H7B	109.5
O1—Mn1—N1	143.66 (5)	C1—C7—H7C	109.5
O1ⁱ—Mn1—N1ⁱ	143.66 (5)	H7A—C7—H7C	109.5
O1—Mn1—N1ⁱ	103.14 (5)	H7B—C7—H7C	109.5
N1—Mn1—N1ⁱ	75.38 (7)	O2—C14—O1	120.11 (16)
O1ⁱ—Mn1—O2ⁱ	58.05 (5)	O2—C14—C8'	122.0 (2)
O1—Mn1—O2ⁱ	113.54 (5)	O1—C14—C8'	117.7 (2)
N1—Mn1—O2ⁱ	102.68 (5)	O2—C14—C8	118.01 (19)
N1ⁱ—Mn1—O2ⁱ	86.43 (4)	O1—C14—C8	121.78 (19)
O1ⁱ—Mn1—O2	113.54 (5)	C8'—C14—C8	8.4 (2)
O1—Mn1—O2	58.05 (5)	O2—C14—Mn1	63.17 (10)
N1—Mn1—O2	86.43 (4)	O1—C14—Mn1	56.94 (9)
N1ⁱ—Mn1—O2	102.68 (5)	C8'—C14—Mn1	173.3 (2)
O2ⁱ—Mn1—O2	168.59 (7)	C8—C14—Mn1	176.64 (15)
O1ⁱ—Mn1—C14ⁱ	29.07 (5)

C13—C8—C9—C10	0.1 (2)	N1—C1—C2—C3	−0.5 (3)
C14—C8—C9—C10	−179.1 (3)	C7—C1—C2—C3	179.08 (17)
C8—C9—C10—C11	−0.1 (2)	C1—C2—C3—C4	−0.6 (3)
C9—C10—C11—C12	0.3 (4)	C2—C3—C4—C5	0.8 (2)
C10—C11—C12—C13	−0.4 (6)	C2—C3—C4—C6	−179.22 (17)
C11—C12—C13—C8	0.4 (5)	C1—N1—C5—C4	−1.0 (2)
C9—C8—C13—C12	−0.3 (4)	Mn1—N1—C5—C4	−179.99 (11)
C14—C8—C13—C12	179.0 (3)	C1—N1—C5—C5ⁱ	178.91 (16)
C13'—C8'—C9'—C10'	0.0 (2)	Mn1—N1—C5—C5ⁱ	0.0 (2)
C14—C8'—C9'—C10'	−179.2 (3)	C3—C4—C5—N1	0.0 (2)
C8'—C9'—C10'—C11'	0.0 (3)	C6—C4—C5—N1	−179.98 (14)
C9'—C10'—C11'—C12'	−0.2 (5)	C3—C4—C5—C5ⁱ	−179.96 (16)
C10'—C11'—C12'—C13'	0.4 (7)	C6—C4—C5—C5ⁱ	0.1 (3)
C9'—C8'—C13'—C12'	0.2 (5)	C3—C4—C6—C6ⁱ	179.9 (2)
C14—C8'—C13'—C12'	179.4 (4)	C5—C4—C6—C6ⁱ	−0.2 (3)
C11'—C12'—C13'—C8'	−0.4 (6)	Mn1—O2—C14—O1	0.18 (17)
O1ⁱ—Mn1—O1—C14	−112.38 (12)	Mn1—O2—C14—C8'	175.0 (2)
N1—Mn1—O1—C14	13.89 (16)	Mn1—O2—C14—C8	−176.45 (17)
N1ⁱ—Mn1—O1—C14	97.00 (11)	Mn1—O1—C14—O2	−0.20 (18)
O2ⁱ—Mn1—O1—C14	−171.16 (10)	Mn1—O1—C14—C8'	−175.22 (19)
O2—Mn1—O1—C14	0.11 (10)	Mn1—O1—C14—C8	176.31 (17)
C14ⁱ—Mn1—O1—C14	−140.61 (10)	C13'—C8'—C14—O2	−169.1 (3)
O1ⁱ—Mn1—O2—C14	85.24 (11)	C9'—C8'—C14—O2	10.1 (4)
O1—Mn1—O2—C14	−0.11 (10)	C13'—C8'—C14—O1	5.8 (4)
N1—Mn1—O2—C14	−171.97 (11)	C9'—C8'—C14—O1	−175.0 (2)
N1ⁱ—Mn1—O2—C14	−97.83 (10)	C13'—C8'—C14—C8	126.9 (18)
O2ⁱ—Mn1—O2—C14	44.60 (10)	C9'—C8'—C14—C8	−54.0 (17)
C14ⁱ—Mn1—O2—C14	78.26 (16)	C9—C8—C14—O2	−23.5 (3)
O1ⁱ—Mn1—N1—C1	38.62 (13)	C13—C8—C14—O2	157.3 (2)
O1—Mn1—N1—C1	−86.43 (15)	C9—C8—C14—O1	159.9 (2)
N1ⁱ—Mn1—N1—C1	−178.83 (15)	C13—C8—C14—O1	−19.3 (3)
O2ⁱ—Mn1—N1—C1	98.32 (13)	C9—C8—C14—C8'	96.7 (17)
O2—Mn1—N1—C1	−74.74 (13)	C13—C8—C14—C8'	−82.5 (17)
C14ⁱ—Mn1—N1—C1	68.55 (13)	O1ⁱ—Mn1—C14—O2	−105.89 (11)
C14—Mn1—N1—C1	−79.02 (13)	O1—Mn1—C14—O2	179.81 (17)
O1ⁱ—Mn1—N1—C5	−142.54 (10)	N1—Mn1—C14—O2	8.85 (12)
O1—Mn1—N1—C5	92.42 (13)	N1ⁱ—Mn1—C14—O2	89.41 (11)
N1ⁱ—Mn1—N1—C5	0.01 (7)	O2ⁱ—Mn1—C14—O2	−166.93 (8)
O2ⁱ—Mn1—N1—C5	−82.83 (10)	C14ⁱ—Mn1—C14—O2	−129.28 (11)
O2—Mn1—N1—C5	104.11 (10)	O1ⁱ—Mn1—C14—O1	74.30 (14)
C14ⁱ—Mn1—N1—C5	−112.61 (10)	N1—Mn1—C14—O1	−170.96 (11)
C14—Mn1—N1—C5	99.82 (10)	N1ⁱ—Mn1—C14—O1	−90.40 (11)
C5—N1—C1—C2	1.3 (2)	O2ⁱ—Mn1—C14—O1	13.26 (15)
Mn1—N1—C1—C2	−179.91 (11)	O2—Mn1—C14—O1	−179.81 (17)
C5—N1—C1—C7	−178.30 (14)	C14ⁱ—Mn1—C14—O1	50.91 (10)
Mn1—N1—C1—C7	0.5 (2)

Symmetry code: (i) −x+2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Mn(C₇H₅O₂)₂(C₁₄H₁₂N₂)]
M_r	505.42
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	291
a, b, c (Å)	17.7020 (19), 14.3903 (16), 9.5678 (11)
β (°)	91.431 (1)
V (Å³)	2436.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.58
Crystal size (mm)	0.43 × 0.24 × 0.21

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.789, 0.886
No. of measured, independent and observed [I > 2σ(I)] reflections	9141, 2274, 1940
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.094, 1.06
No. of reflections	2274
No. of parameters	179
No. of restraints	93
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.30

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

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