Chlorido{5,5′-dimethyl-2,2′-[1,2-phenyl­enebis(nitrilo­methyl­idyne)]diphenolato-κ4O,N,N′,O′}manganese(III)

Eltayeb, N.E.; Teoh, S.G.; Chantrapromma, S.; Fun, H.-K.; Adnan, R.

doi:10.1107/S1600536808007459

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 4| April 2008| Pages m570-m571

doi:10.1107/S1600536808007459

Open

access

Chlorido{5,5′-dimethyl-2,2′-[1,2-phenylenebis(nitrilomethylidyne)]diphenolato-κ⁴O,N,N′,O′}manganese(III)

Naser Eltaher Eltayeb,^a ‡ Siang Guan Teoh,^a Suchada Chantrapromma,^b § Hoong-Kun Fun ^c ^* and Rohana Adnan ^a

^aSchool of Chemical Science, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 15 March 2008; accepted 18 March 2008; online 29 March 2008)

In the title complex, [Mn(C₂₂H₁₈N₂O₂)Cl], the Mn^III center is in a distorted square-pyramidal configuration; the basal plane is formed by the N₂O₂ donors of the tetradentate Schiff base dianion, with the two phenol O atoms and two imine N atoms each mutually cis. The chloride ion occupies the apical coordination site. The dihedral angle between the two outer phenolate rings of the tetradentate ligand is 18.24 (9)°. The central benzene ring makes dihedral angles of 13.71 (8) and 30.50 (8)° with the two outer phenolate rings. In the crystal structure, weak C—H⋯Cl interactions link the molecules into screw helices along the b direction. These helices are further connected by weak C—H⋯O interactions into a three-dimensional network. The crystal structure is further stabilized by C—H⋯π interactions involving the central benzene ring.

Related literature

For values of bond lengths, see: Allen et al. (1987 ). For details of ring conformations, see: Cremer & Pople (1975 ). For related structures, see, for example: Eltayeb et al. (2008 ); Habibi et al. (2007 ); Mitra et al. (2006 ). For background to applications of manganese complexes, see, for example: Dixit & Srinivasan (1988 ); Glatzel et al. (2004 ); Lu et al. (2006 ); Stallings et al. (1985 ).

Experimental

Crystal data

[Mn(C₂₂H₁₈N₂O₂)Cl]
M_r = 432.77
Monoclinic, C 2/c
a = 20.9593 (5) Å
b = 13.5897 (3) Å
c = 14.9316 (3) Å
β = 119.641 (1)°
V = 3696.43 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.88 mm⁻¹
T = 100.0 (1) K
0.56 × 0.20 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.639, T_max = 0.852
35769 measured reflections
8109 independent reflections
5992 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.126
S = 1.07
8109 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯Cl1ⁱ	0.93	2.77	3.6508 (16)	158
C7—H7A⋯Cl1ⁱ	0.93	2.81	3.6933 (15)	158
C11—H11A⋯O1ⁱⁱ	0.93	2.58	3.423 (2)	151
C4—H4A⋯Cg1ⁱⁱⁱ	0.93	2.83	3.5443 (19)	135
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y-1, z-{\script{1\over 2}}]$ . Cg1 is the centroid of the C8–C13 benzene ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808007459/sj2474sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808007459/sj2474Isup2.hkl

checkCIF report

Comment top

We have been interested in syntheses of Schiff base ligands containing oxygen and imine nitrogen atoms and their metal complexes due to their variety of applications. Manganese complexes with Schiff base ligands have numerous applications in chemistry, biology, physics and advanced materials and are used in catalysis (Dixit and Srinivasan, 1988), as models for the oxygen-evolving complex of photosystem II (Glatzel et al., 2004), and as single-molecule magnets (Lu et al., 2006). They also serve as models for the active sites of manganese-containing metal enzymes (Stallings et al., 1985). Recently, we reported the crystal structure of a five coordinate Mn^III complex with a similar N₂O₂ donor Schiff base ligand, chlorido{6,6'-dimethyl-2,2'-[1,2-phenylenebis(nitrilomethylidene)]diphenolato- κ⁴O,N,N',O'}manganese(III) monohydrate (Eltayeb et al., 2008). We report here the structure of (I), Fig. 1, a Mn^III complex of a closely-related ligand.

In (I) the Mn^III center is in a slightly distorted square-pyramidal geometry coordinating through N1, N2, O1 and O2 atoms of the tetradentate Schiff base ligand in the basal plane with the two phenolic O atoms and two imine N atoms in mutually cis positions. The apical position is coordinated by the Cl^- ion. The Mn—O distances [Mn1—O1 = 1.8698 (12)Å, Mn1—O2 = 1.8983 (10)Å] and Mn—N distances [Mn1—N1 = 1.9923 (12)Å, Mn1—N2 = 1.9875 (12)Å] are in the same ranges of those observed in other related Mn^III complexes of N₂O₂ Schiff base ligands (Eltayeb et al., 2008; Habibi et al., 2007; Mitra et al., 2006). Other bond lengths and angles observed in the structure are also normal (Allen et al., 1987). The basal bond angles O1–Mn1–O2 of 92.61 (4)°, O–Mn–N [O1–Mn1–N1 = 93.07 (5)°, O2–Mn1–N2 = 89.21 (5)°] are close to 90° whereas the N–Mn–N is smaller than 90° [N1–Mn1–N2 = 82.10 (5)°]. The bond angles between the Cl^- ion and the atoms in the basal plane are in the range 93.14 (4) to 99.97 (4)°, indicating a distorted square-pyramidal geometry. Coordination of the the N₂O₂ chelate ligand to the Mn^III ion results in the formation of an essentialy planar five-membered ring (Mn1/N1/N2/C8/C13) and two six-membered rings; the Mn1/O1/N1/C1/C6/C7 ring is almost planar with the greatest deviation being 0.059 (1)Å for atom O2 whereas the Mn1/O2/N2/C14/C15/C20 ring adopts an envelope conformation with atom O2 displaced from the Mn1/N2/C14/C15/C20 plane by 0.298 (1)Å and with Cremer & Pople (1975) puckering parameters Q = 0.483 (1)°, θ = 61.0 (1)° and ϕ = 18.8 (2)°. These parameters are larger in values than those observed in the closely-related structure (Eltayeb et al., 2008). The dihedral angle between the two outer phenolate rings [C1–C6 and C15–C20] of the Schiff base ligand is 18.24 (9)°. The central benzene ring (C8–C13) makes dihedral angles of 13.71 (8)° and 30.50 (8)° with the two outer phenolate rings. These dihedral angles are all wider than the corresponding angles found in a closely related structure (Eltayeb et al., 2008) due to the different locations of the two methyl substituents on the phenolate rings of the Schiff base ligand.

In the crystal packing (Fig. 2), weak C—H···Cl interactions (Table 1) link the molecules into screw helices along the b direction. These helices are further connected by weak C—H···O interactions into a three-dimensional network. The crystal is further stabilized by weak C—H···π interactions (Table 1); Cg₁ is the centroid of the C8–C13 benzene ring.

Related literature top

For values of bond lengths, see: Allen et al. (1987). For details of ring conformations, see: Cremer & Pople (1975). For related structures, see, for example: Eltayeb et al. (2008); Habibi et al. (2007); Mitra et al. (2006). For background to applications of manganese complexes, see, for example: Dixit & Srinivasan (1988); Glatzel et al. (2004); Lu et al. (2006); Stallings et al. (1985).

Experimental top

The title compound was synthesized by adding 2-hydroxy-4-methylbenzaldehyde (0.546 g, 4 mmol) to a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol 95% (30 ml). The mixture was refluxed with stirring for half an hour. Manganese chloride tetrahydrate (0.394 g, 2 mmol) in ethanol (10 ml) was then added, followed by triethylamine (0.5 ml, 3.6 mmol). The mixture was refluxed at room temperature for three hours. A brown precipitate was obtained, washed with about 5 ml ethanol, dried, and then washed with copious quantities of diethylether. Brown single crystals of the title compound suitable for x-ray structure determination were recrystallized from ethanol/methanol (2:1 v/v) by slow evaporation of the solvent at room temperature over two months.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. The crystal packing of (I), viewed along the a axis, showing the three-dimensional network. C—H···Cl weak interactions are drawn as dashed lines.

Chlorido{5,5'-dimethyl-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenolato- κ⁴O,N,N',O'}manganese(III) top

Crystal data top

[Mn(C₂₂H₁₈N₂O₂)Cl]	F(000) = 1776
M_r = 432.77	D_x = 1.555 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8109 reflections
a = 20.9593 (5) Å	θ = 2.1–35.0°
b = 13.5897 (3) Å	µ = 0.88 mm⁻¹
c = 14.9316 (3) Å	T = 100 K
β = 119.641 (1)°	Block, brown
V = 3696.43 (14) Å³	0.56 × 0.20 × 0.19 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	8109 independent reflections
Radiation source: fine-focus sealed tube	5992 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
Detector resolution: 8.33 pixels mm^-1	θ_max = 35.0°, θ_min = 2.1°
ω scans	h = −33→28
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −21→21
T_min = 0.639, T_max = 0.852	l = −23→24
35769 measured reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0635P)² + 1.3131P] where P = (F_o² + 2F_c²)/3
8109 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 0.75 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

[Mn(C₂₂H₁₈N₂O₂)Cl]	V = 3696.43 (14) Å³
M_r = 432.77	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 20.9593 (5) Å	µ = 0.88 mm⁻¹
b = 13.5897 (3) Å	T = 100 K
c = 14.9316 (3) Å	0.56 × 0.20 × 0.19 mm
β = 119.641 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	8109 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	5992 reflections with I > 2σ(I)
T_min = 0.639, T_max = 0.852	R_int = 0.048
35769 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.07	Δρ_max = 0.75 e Å⁻³
8109 reflections	Δρ_min = −0.69 e Å⁻³
255 parameters

Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Mn1	0.225261 (11)	0.228215 (15)	0.091917 (16)	0.01606 (6)
Cl1	0.16386 (2)	0.29835 (3)	0.17860 (3)	0.02432 (9)
O1	0.14852 (6)	0.14593 (7)	0.00249 (8)	0.0192 (2)
O2	0.19870 (6)	0.32753 (7)	−0.00984 (8)	0.0185 (2)
N1	0.27984 (6)	0.11876 (9)	0.18852 (9)	0.0168 (2)
N2	0.31816 (6)	0.30016 (9)	0.18058 (9)	0.0167 (2)
C1	0.13609 (8)	0.05345 (10)	0.01522 (11)	0.0174 (3)
C2	0.07011 (8)	0.00997 (11)	−0.05872 (12)	0.0219 (3)
H2A	0.0365	0.0481	−0.1136	0.026*
C3	0.05302 (8)	−0.08722 (11)	−0.05333 (12)	0.0209 (3)
C4	0.10445 (9)	−0.14629 (12)	0.02727 (12)	0.0226 (3)
H4A	0.0941	−0.2121	0.0314	0.027*
C5	0.17011 (8)	−0.10657 (11)	0.10001 (11)	0.0209 (3)
H5A	0.2043	−0.1468	0.1520	0.025*
C6	0.18698 (8)	−0.00631 (10)	0.09789 (10)	0.0168 (2)
C7	0.25658 (8)	0.02818 (11)	0.17669 (10)	0.0173 (2)
H7A	0.2881	−0.0180	0.2237	0.021*
C8	0.35313 (7)	0.14389 (11)	0.26289 (10)	0.0177 (3)
C9	0.40356 (8)	0.08078 (12)	0.33913 (12)	0.0233 (3)
H9A	0.3889	0.0190	0.3489	0.028*
C10	0.47580 (8)	0.11154 (13)	0.40001 (12)	0.0263 (3)
H10A	0.5094	0.0701	0.4512	0.032*
C11	0.49860 (8)	0.20291 (13)	0.38569 (12)	0.0258 (3)
H11A	0.5475	0.2215	0.4251	0.031*
C12	0.44804 (8)	0.26669 (12)	0.31221 (12)	0.0229 (3)
H12A	0.4631	0.3282	0.3024	0.027*
C13	0.37498 (8)	0.23870 (11)	0.25325 (11)	0.0174 (3)
C14	0.32367 (8)	0.39542 (11)	0.17937 (11)	0.0193 (3)
H14A	0.3669	0.4242	0.2297	0.023*
C15	0.26777 (8)	0.45912 (10)	0.10593 (11)	0.0179 (3)
C16	0.27519 (9)	0.56198 (11)	0.12163 (12)	0.0216 (3)
H16A	0.3150	0.5867	0.1811	0.026*
C17	0.22469 (9)	0.62645 (11)	0.05081 (12)	0.0235 (3)
H17A	0.2306	0.6938	0.0630	0.028*
C18	0.16426 (9)	0.59053 (11)	−0.03985 (12)	0.0216 (3)
C19	0.15624 (8)	0.48953 (11)	−0.05583 (11)	0.0196 (3)
H19A	0.1159	0.4657	−0.1152	0.024*
C20	0.20661 (8)	0.42298 (10)	0.01426 (11)	0.0176 (3)
C21	−0.01947 (9)	−0.12957 (13)	−0.13236 (15)	0.0305 (4)
H21A	−0.0443	−0.0835	−0.1878	0.046*
H21B	−0.0491	−0.1423	−0.1011	0.046*
H21C	−0.0114	−0.1899	−0.1587	0.046*
C22	0.10955 (10)	0.65886 (13)	−0.12034 (14)	0.0305 (4)
H22A	0.1032	0.6414	−0.1866	0.046*
H22B	0.1271	0.7253	−0.1040	0.046*
H22C	0.0634	0.6535	−0.1218	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.01366 (10)	0.01200 (11)	0.01705 (10)	−0.00147 (7)	0.00341 (7)	0.00028 (7)
Cl1	0.02102 (17)	0.02319 (18)	0.02899 (18)	−0.00435 (13)	0.01255 (14)	−0.00675 (13)
O1	0.0161 (5)	0.0125 (4)	0.0212 (5)	−0.0013 (4)	0.0033 (4)	0.0006 (3)
O2	0.0210 (5)	0.0112 (4)	0.0180 (4)	−0.0003 (4)	0.0057 (4)	−0.0002 (3)
N1	0.0142 (5)	0.0162 (5)	0.0164 (5)	−0.0010 (4)	0.0049 (4)	0.0001 (4)
N2	0.0142 (5)	0.0148 (5)	0.0183 (5)	−0.0012 (4)	0.0058 (4)	−0.0014 (4)
C1	0.0150 (6)	0.0136 (6)	0.0218 (6)	−0.0009 (5)	0.0077 (5)	−0.0011 (5)
C2	0.0139 (6)	0.0168 (7)	0.0271 (7)	−0.0012 (5)	0.0041 (5)	−0.0017 (5)
C3	0.0149 (6)	0.0174 (7)	0.0280 (7)	−0.0028 (5)	0.0087 (5)	−0.0033 (5)
C4	0.0251 (7)	0.0174 (7)	0.0250 (7)	−0.0053 (6)	0.0121 (6)	−0.0018 (5)
C5	0.0231 (7)	0.0147 (6)	0.0214 (6)	−0.0012 (5)	0.0084 (5)	0.0013 (5)
C6	0.0153 (6)	0.0146 (6)	0.0188 (6)	−0.0016 (5)	0.0070 (5)	0.0000 (4)
C7	0.0175 (6)	0.0154 (6)	0.0170 (5)	0.0002 (5)	0.0070 (5)	0.0012 (4)
C8	0.0133 (6)	0.0181 (6)	0.0180 (6)	0.0000 (5)	0.0049 (5)	−0.0002 (5)
C9	0.0166 (6)	0.0227 (7)	0.0230 (6)	0.0002 (5)	0.0041 (5)	0.0039 (5)
C10	0.0166 (7)	0.0282 (8)	0.0242 (7)	0.0023 (6)	0.0025 (5)	0.0038 (6)
C11	0.0142 (6)	0.0295 (8)	0.0264 (7)	−0.0010 (6)	0.0044 (5)	−0.0017 (6)
C12	0.0149 (6)	0.0217 (7)	0.0272 (7)	−0.0028 (5)	0.0067 (5)	−0.0032 (5)
C13	0.0144 (6)	0.0171 (6)	0.0178 (6)	−0.0011 (5)	0.0057 (5)	−0.0022 (5)
C14	0.0181 (6)	0.0172 (6)	0.0205 (6)	−0.0037 (5)	0.0080 (5)	−0.0031 (5)
C15	0.0171 (6)	0.0129 (6)	0.0223 (6)	−0.0023 (5)	0.0087 (5)	−0.0011 (5)
C16	0.0233 (7)	0.0155 (6)	0.0253 (7)	−0.0033 (5)	0.0115 (6)	−0.0026 (5)
C17	0.0280 (8)	0.0132 (6)	0.0308 (7)	−0.0001 (5)	0.0158 (6)	−0.0011 (5)
C18	0.0250 (7)	0.0171 (7)	0.0247 (7)	0.0029 (5)	0.0139 (6)	0.0022 (5)
C19	0.0210 (7)	0.0163 (6)	0.0212 (6)	0.0012 (5)	0.0102 (5)	0.0003 (5)
C20	0.0191 (6)	0.0138 (6)	0.0201 (6)	−0.0016 (5)	0.0097 (5)	−0.0006 (5)
C21	0.0176 (7)	0.0219 (8)	0.0417 (9)	−0.0054 (6)	0.0068 (6)	−0.0063 (7)
C22	0.0371 (9)	0.0193 (7)	0.0317 (8)	0.0082 (7)	0.0143 (7)	0.0026 (6)

Geometric parameters (Å, º) top

Mn1—O1	1.8698 (10)	C9—H9A	0.9300
Mn1—O2	1.8983 (10)	C10—C11	1.385 (2)
Mn1—N2	1.9875 (12)	C10—H10A	0.9300
Mn1—N1	1.9923 (12)	C11—C12	1.388 (2)
Mn1—Cl1	2.4263 (4)	C11—H11A	0.9300
O1—C1	1.3162 (17)	C12—C13	1.390 (2)
O2—C20	1.3344 (17)	C12—H12A	0.9300
N1—C7	1.3034 (18)	C14—C15	1.433 (2)
N1—C8	1.4221 (17)	C14—H14A	0.9300
N2—C14	1.3006 (19)	C15—C16	1.413 (2)
N2—C13	1.4195 (18)	C15—C20	1.4221 (19)
C1—C2	1.4036 (19)	C16—C17	1.378 (2)
C1—C6	1.4208 (19)	C16—H16A	0.9300
C2—C3	1.381 (2)	C17—C18	1.407 (2)
C2—H2A	0.9300	C17—H17A	0.9300
C3—C4	1.404 (2)	C18—C19	1.389 (2)
C3—C21	1.503 (2)	C18—C22	1.503 (2)
C4—C5	1.373 (2)	C19—C20	1.391 (2)
C4—H4A	0.9300	C19—H19A	0.9300
C5—C6	1.412 (2)	C21—H21A	0.9600
C5—H5A	0.9300	C21—H21B	0.9600
C6—C7	1.4263 (19)	C21—H21C	0.9600
C7—H7A	0.9300	C22—H22A	0.9600
C8—C13	1.398 (2)	C22—H22B	0.9600
C8—C9	1.399 (2)	C22—H22C	0.9600
C9—C10	1.390 (2)

O1—Mn1—O2	92.61 (4)	C11—C10—C9	121.08 (14)
O1—Mn1—N2	169.49 (5)	C11—C10—H10A	119.5
O2—Mn1—N2	89.21 (5)	C9—C10—H10A	119.5
O1—Mn1—N1	93.07 (5)	C10—C11—C12	119.67 (14)
O2—Mn1—N1	161.15 (5)	C10—C11—H11A	120.2
N2—Mn1—N1	82.10 (5)	C12—C11—H11A	120.2
O1—Mn1—Cl1	96.89 (4)	C11—C12—C13	120.06 (15)
O2—Mn1—Cl1	97.16 (4)	C11—C12—H12A	120.0
N2—Mn1—Cl1	93.14 (4)	C13—C12—H12A	120.0
N1—Mn1—Cl1	99.97 (4)	C12—C13—C8	120.09 (13)
C1—O1—Mn1	129.03 (9)	C12—C13—N2	124.62 (14)
C20—O2—Mn1	121.82 (9)	C8—C13—N2	115.29 (12)
C7—N1—C8	121.32 (12)	N2—C14—C15	124.56 (13)
C7—N1—Mn1	124.38 (10)	N2—C14—H14A	117.7
C8—N1—Mn1	113.44 (9)	C15—C14—H14A	117.7
C14—N2—C13	123.34 (12)	C16—C15—C20	118.30 (13)
C14—N2—Mn1	123.02 (10)	C16—C15—C14	119.30 (13)
C13—N2—Mn1	113.25 (9)	C20—C15—C14	122.31 (13)
O1—C1—C2	118.48 (13)	C17—C16—C15	121.46 (14)
O1—C1—C6	123.65 (12)	C17—C16—H16A	119.3
C2—C1—C6	117.84 (13)	C15—C16—H16A	119.3
C3—C2—C1	122.67 (14)	C16—C17—C18	120.13 (14)
C3—C2—H2A	118.7	C16—C17—H17A	119.9
C1—C2—H2A	118.7	C18—C17—H17A	119.9
C2—C3—C4	119.04 (13)	C19—C18—C17	118.89 (14)
C2—C3—C21	120.74 (14)	C19—C18—C22	119.57 (14)
C4—C3—C21	120.23 (14)	C17—C18—C22	121.52 (14)
C5—C4—C3	119.82 (14)	C18—C19—C20	122.06 (14)
C5—C4—H4A	120.1	C18—C19—H19A	119.0
C3—C4—H4A	120.1	C20—C19—H19A	119.0
C4—C5—C6	121.72 (14)	O2—C20—C19	118.83 (13)
C4—C5—H5A	119.1	O2—C20—C15	121.86 (13)
C6—C5—H5A	119.1	C19—C20—C15	119.15 (13)
C5—C6—C1	118.84 (12)	C3—C21—H21A	109.5
C5—C6—C7	117.65 (13)	C3—C21—H21B	109.5
C1—C6—C7	123.43 (13)	H21A—C21—H21B	109.5
N1—C7—C6	125.70 (13)	C3—C21—H21C	109.5
N1—C7—H7A	117.2	H21A—C21—H21C	109.5
C6—C7—H7A	117.2	H21B—C21—H21C	109.5
C13—C8—C9	119.63 (13)	C18—C22—H22A	109.5
C13—C8—N1	115.03 (12)	C18—C22—H22B	109.5
C9—C8—N1	125.29 (13)	H22A—C22—H22B	109.5
C10—C9—C8	119.20 (15)	C18—C22—H22C	109.5
C10—C9—H9A	120.4	H22A—C22—H22C	109.5
C8—C9—H9A	120.4	H22B—C22—H22C	109.5

O2—Mn1—O1—C1	170.43 (13)	C5—C6—C7—N1	−177.31 (15)
N2—Mn1—O1—C1	70.7 (3)	C1—C6—C7—N1	6.2 (2)
N1—Mn1—O1—C1	8.41 (13)	C7—N1—C8—C13	167.53 (14)
Cl1—Mn1—O1—C1	−92.03 (12)	Mn1—N1—C8—C13	−2.25 (16)
O1—Mn1—O2—C20	145.34 (11)	C7—N1—C8—C9	−9.7 (2)
N2—Mn1—O2—C20	−45.01 (11)	Mn1—N1—C8—C9	−179.47 (13)
N1—Mn1—O2—C20	−107.23 (17)	C13—C8—C9—C10	−3.8 (2)
Cl1—Mn1—O2—C20	48.06 (11)	N1—C8—C9—C10	173.30 (15)
O1—Mn1—N1—C7	−1.63 (13)	C8—C9—C10—C11	−0.6 (3)
O2—Mn1—N1—C7	−108.98 (16)	C9—C10—C11—C12	2.6 (3)
N2—Mn1—N1—C7	−172.25 (13)	C10—C11—C12—C13	−0.1 (3)
Cl1—Mn1—N1—C7	95.93 (12)	C11—C12—C13—C8	−4.3 (2)
O1—Mn1—N1—C8	167.79 (10)	C11—C12—C13—N2	176.11 (15)
O2—Mn1—N1—C8	60.44 (19)	C9—C8—C13—C12	6.3 (2)
N2—Mn1—N1—C8	−2.83 (10)	N1—C8—C13—C12	−171.13 (14)
Cl1—Mn1—N1—C8	−94.65 (10)	C9—C8—C13—N2	−174.11 (13)
O1—Mn1—N2—C14	131.1 (2)	N1—C8—C13—N2	8.51 (19)
O2—Mn1—N2—C14	31.04 (12)	C14—N2—C13—C12	−18.1 (2)
N1—Mn1—N2—C14	−165.73 (13)	Mn1—N2—C13—C12	168.88 (13)
Cl1—Mn1—N2—C14	−66.09 (12)	C14—N2—C13—C8	162.28 (14)
O1—Mn1—N2—C13	−55.8 (3)	Mn1—N2—C13—C8	−10.73 (16)
O2—Mn1—N2—C13	−155.92 (10)	C13—N2—C14—C15	178.88 (14)
N1—Mn1—N2—C13	7.31 (10)	Mn1—N2—C14—C15	−8.8 (2)
Cl1—Mn1—N2—C13	106.95 (10)	N2—C14—C15—C16	170.29 (15)
Mn1—O1—C1—C2	173.26 (11)	N2—C14—C15—C20	−13.2 (2)
Mn1—O1—C1—C6	−9.1 (2)	C20—C15—C16—C17	0.3 (2)
O1—C1—C2—C3	178.35 (15)	C14—C15—C16—C17	176.93 (15)
C6—C1—C2—C3	0.6 (2)	C15—C16—C17—C18	−0.3 (2)
C1—C2—C3—C4	−2.1 (2)	C16—C17—C18—C19	0.6 (2)
C1—C2—C3—C21	177.86 (16)	C16—C17—C18—C22	−177.92 (16)
C2—C3—C4—C5	1.0 (2)	C17—C18—C19—C20	−0.9 (2)
C21—C3—C4—C5	−179.03 (16)	C22—C18—C19—C20	177.67 (15)
C3—C4—C5—C6	1.7 (2)	Mn1—O2—C20—C19	−146.85 (11)
C4—C5—C6—C1	−3.3 (2)	Mn1—O2—C20—C15	37.70 (18)
C4—C5—C6—C7	−179.96 (15)	C18—C19—C20—O2	−174.69 (14)
O1—C1—C6—C5	−175.56 (14)	C18—C19—C20—C15	0.9 (2)
C2—C1—C6—C5	2.1 (2)	C16—C15—C20—O2	174.89 (14)
O1—C1—C6—C7	0.9 (2)	C14—C15—C20—O2	−1.6 (2)
C2—C1—C6—C7	178.55 (14)	C16—C15—C20—C19	−0.6 (2)
C8—N1—C7—C6	−173.22 (14)	C14—C15—C20—C19	−177.07 (14)
Mn1—N1—C7—C6	−4.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···Cl1ⁱ	0.93	2.77	3.6508 (16)	158
C7—H7A···Cl1ⁱ	0.93	2.81	3.6933 (15)	158
C11—H11A···O1ⁱⁱ	0.93	2.58	3.423 (2)	151
C4—H4A···Cg1ⁱⁱⁱ	0.93	2.83	3.5443 (19)	135

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) x, −y−1, z−1/2.

Experimental details

Crystal data
Chemical formula	[Mn(C₂₂H₁₈N₂O₂)Cl]
M_r	432.77
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	20.9593 (5), 13.5897 (3), 14.9316 (3)
β (°)	119.641 (1)
V (Å³)	3696.43 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.88
Crystal size (mm)	0.56 × 0.20 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.639, 0.852
No. of measured, independent and observed [I > 2σ(I)] reflections	35769, 8109, 5992
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.807

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.126, 1.07
No. of reflections	8109
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.69

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···Cl1ⁱ	0.93	2.7705	3.6508 (16)	158
C7—H7A···Cl1ⁱ	0.93	2.8139	3.6933 (15)	158
C11—H11A···O1ⁱⁱ	0.93	2.5776	3.423 (2)	151
C4—H4A···Cg1ⁱⁱⁱ	0.93	2.8292	3.5443 (19)	135

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) x, −y−1, z−1/2.

Footnotes

‡On study leave from International University of Africa, Sudan. E-mail: nasertaha90@hotmail.com.

§Additional correspondence author, e-mail: suchada.c@psu.ac.th.

Acknowledgements

The authors thank the Malaysian Government, Ministry of Science, Technology and Innovation (MOSTI), and Universiti Sains Malaysia for the E-Science Fund research grant (PKIMIA/613308) and facilities. The International University of Africa (Sudan) is acknowledged for providing study leave to NEE. The authors also thank Universiti Sains Malaysia for the Fundamental Research Grant Scheme (FRGS) grant No. 203/PFIZIK/671064.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CrossRef Web of Science Google Scholar
Bruker (2005). APEX2 (Version 1.27), SAINT (Version 7.12A) and SADABS (Version 2004/1). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Dixit, P. S. & Srinivasan, K. (1988). Inorg. Chem. 27, 4507–4509. CrossRef CAS Web of Science Google Scholar
Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Adnan, R. (2008). Acta Cryst. E64, m535–m536. Web of Science CSD CrossRef IUCr Journals Google Scholar
Glatzel, P., Bergmann, U., Yano, J., Visser, H., Robblee, J. H., Gu, W., de Groot, F. M. F., Christou, G., Pecoraro, V. L., Cramer, S. P. & Yachandra, V. K. (2004). J. Am. Chem. Soc. 126, 9946–9959. Web of Science CrossRef PubMed CAS Google Scholar
Habibi, M. H., Askari, E., Chantrapromma, S. & Fun, H.-K. (2007). Acta Cryst. E63, m2905–m2906. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lu, Z., Yuan, M., Pan, F., Gao, S., Zhang, D. & Zhu, D. (2006). Inorg. Chem. 45, 3538–3548. Web of Science CSD CrossRef PubMed Google Scholar
Mitra, K., Biswas, S., Lucas, C. R. & Adhikary, B. (2006). Inorg. Chim. Acta, 359, 1997–2003. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stallings, W. C., Pattridge, K. A., Strong, R. K. & Ludwig, M. L. (1985). J. Biol. Chem. 260, 16424–16432. CAS PubMed Web of Science Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.