(Dimethyl sulfoxide-κO)(2-formyl­phenolato-κ2O,O′)[2-(2-oxidobenzyl­idene­amino)­phenolato-κ3O,N,O′]manganese(III)

Raja, I.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536811015935

metal-organic compounds

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Volume 67| Part 6| June 2011| Page m674

doi:10.1107/S1600536811015935

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(Dimethyl sulfoxide-κO)(2-formylphenolato-κ²O,O′)[2-(2-oxidobenzylideneamino)phenolato-κ³O,N,O′]manganese(III)

Inba Raja,^a Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 25 April 2011; accepted 27 April 2011; online 7 May 2011)

The O-C₆H₄-CH=N–C₆H₄-O dianion of the title compound, [Mn(C₁₃H₉NO₂)(C₇H₅O₂)(C₂H₆OS)], acts as an O,N,O′-chelate to bind to the Mn^III atom, and the three atoms constitute three points [O—Mn—O = 174.43 (11)°] of an octahedron around the metal atom. The azomethine linkage is disordered over two positions in a 0.657 (13):0.343 (13) ratio. The deprotonated salicyldehyde anion acts as an O,O′-chelate; the sixth coordination site is represented by the O atom of the dimethyl sulfoxide molecule. The crystal studied was a non-merohedral twin with a minor twin component of 14.2 (3)%.

Related literature

For related Mn^III structures, see: Asada et al. (1999 , 2002 ); Nakamura et al. (1999 , 2001 ).

Experimental

Crystal data

[Mn(C₁₃H₉NO₂)(C₇H₅O₂)(C₂H₆OS)]
M_r = 465.39
Monoclinic, P 2₁ /c
a = 12.1342 (3) Å
b = 20.4224 (5) Å
c = 8.1812 (2) Å
β = 94.692 (2)°
V = 2020.59 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.79 mm⁻¹
T = 100 K
0.15 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (TWINABS; Bruker, 2009 ) T_min = 0.891, T_max = 0.925
39957 measured reflections
5025 independent reflections
3528 reflections with I > 2σ(I)
R_int = 0.091

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.129
S = 1.03
5025 reflections
293 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811015935/hg5028sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015935/hg5028Isup2.hkl

checkCIF report

Comment top

The deprotonated anion of the Schiff base derived by condensing salicylaldehyde and 2-aminophenol, (O–C₆H₄–CH═N–C₆H₄O)^2-, behaves as a terdentate O,N,O' chelate to a number of metal ions. For the manganese ion in particular, the crystal structures of a small number of manganese(III) [2-(2-oxidobenzylideneamino)phenolates have been reported (Asada et al., 1999; Asada et al., 2002; Nakamura et al., 1999; Nakamura et al., 2001). In the present study, the reaction of the Schiff base with an mangasese(III) salt resulted in the cleavage of the azomethine linkage of one half of the molar quantity of the organic reactant. The O–C₆H₄–CH═N–C₆H₄–O dianion of Mn(C₁₃H₉NO₂)(C₇H₅O₃)(DMSO) (Scheme I) acts as an O,N,O'-chelates to bind to the Mn^III atom, and the three atoms constitute three points O–Mn–O 174.4 (1) °] of the octahedron around the metal atom. The azomethine linkage is disordered over two positions in a 66 (1): 34 ratio. The deprotonated salicyldehyde anion acts as an O,O'-chelate; the sixth coordination site is represented by the O atom of the DMSO molecule (Fig. 1).

Related literature top

For related Mn^III structures, see: Asada et al. (1999, 2002); Nakamura et al. (1999, 2001).

Experimental top

2-(Salicylaldimino)phenol was prepared from the condensation reaction of salicyaldehyde and 2-aminophenol. The Schiff base (0.22 g, 1 mmol) and manganese(III) acetate dihydrate (0.23 g, 1 mmol) along with ethanol (100 ml) were heated for an hour until the reactants dissolved completely. A few drops of DMSO were then added. The dark blue solution was then filtered and the solvent allowed to evporate over a few days.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Mn(C₁₃H₉NO₂)(C₇H₅O₃)(C₂H₆OS) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disordered azomethine linkage is shown in two conformations.

(Dimethyl sulfoxide-κO)(2-formylphenolato-κ²O,O')[2-(2- oxidobenzylideneamino)phenolato-κ³O,N,O']manganese(III) top

Crystal data top

[Mn(C₁₃H₉NO₂)(C₇H₅O₂)(C₂H₆OS)]	F(000) = 960
M_r = 465.39	D_x = 1.530 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2199 reflections
a = 12.1342 (3) Å	θ = 2.7–20.7°
b = 20.4224 (5) Å	µ = 0.79 mm⁻¹
c = 8.1812 (2) Å	T = 100 K
β = 94.692 (2)°	Prism, blue
V = 2020.59 (9) Å³	0.15 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	5025 independent reflections
Radiation source: fine-focus sealed tube	3528 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.091
ω scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (TWINABS; Bruker, 2009)	h = −16→16
T_min = 0.891, T_max = 0.925	k = 0→27
39957 measured reflections	l = 0→10

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0473P)² + 1.4711P] where P = (F_o² + 2F_c²)/3
5025 reflections	(Δ/σ)_max = 0.001
293 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

[Mn(C₁₃H₉NO₂)(C₇H₅O₂)(C₂H₆OS)]	V = 2020.59 (9) Å³
M_r = 465.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.1342 (3) Å	µ = 0.79 mm⁻¹
b = 20.4224 (5) Å	T = 100 K
c = 8.1812 (2) Å	0.15 × 0.10 × 0.10 mm
β = 94.692 (2)°

Data collection top

Bruker SMART APEX diffractometer	5025 independent reflections
Absorption correction: multi-scan (TWINABS; Bruker, 2009)	3528 reflections with I > 2σ(I)
T_min = 0.891, T_max = 0.925	R_int = 0.091
39957 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.03	Δρ_max = 0.60 e Å⁻³
5025 reflections	Δρ_min = −0.49 e Å⁻³
293 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Mn1	0.28456 (4)	0.58739 (2)	0.78780 (6)	0.02681 (15)
S1	0.32300 (7)	0.52236 (4)	1.15078 (9)	0.0296 (2)
O1	0.4174 (2)	0.61593 (11)	0.7087 (3)	0.0386 (6)
O2	0.1485 (2)	0.56551 (14)	0.8733 (3)	0.0461 (7)
O3	0.30142 (17)	0.50104 (10)	0.7054 (2)	0.0260 (5)
O4	0.19393 (18)	0.60934 (10)	0.5404 (3)	0.0303 (5)
O5	0.37558 (18)	0.56099 (10)	1.0187 (3)	0.0285 (5)
N1'	0.2928 (8)	0.6891 (5)	0.8183 (10)	0.018 (3)	0.343 (13)
N1	0.2358 (4)	0.6733 (3)	0.8700 (5)	0.0224 (16)	0.657 (13)
C1	0.4451 (3)	0.67812 (16)	0.6932 (4)	0.0302 (7)
C2	0.5410 (3)	0.69431 (17)	0.6183 (4)	0.0311 (7)
H2	0.5868	0.6605	0.5815	0.037*
C3	0.5696 (3)	0.75874 (18)	0.5973 (4)	0.0361 (8)
H3	0.6352	0.7688	0.5467	0.043*
C4	0.5042 (3)	0.80926 (17)	0.6489 (4)	0.0379 (8)
H4	0.5240	0.8536	0.6321	0.045*
C5	0.4111 (3)	0.79438 (17)	0.7238 (4)	0.0371 (8)
H5	0.3664	0.8289	0.7595	0.045*
C6	0.3802 (3)	0.72972 (17)	0.7493 (4)	0.0308 (7)
C7'	0.2227 (8)	0.7190 (6)	0.9041 (11)	0.020 (3)	0.343 (13)
H7'	0.2259	0.7646	0.9260	0.024*	0.343 (13)
C7	0.2828 (5)	0.7279 (4)	0.8393 (7)	0.0250 (17)	0.657 (13)
H7	0.2529	0.7676	0.8766	0.030*	0.657 (13)
C8	0.1373 (3)	0.6757 (2)	0.9648 (4)	0.0398 (9)
C9	0.0843 (3)	0.72355 (18)	1.0517 (4)	0.0451 (10)
H9	0.1126	0.7669	1.0577	0.054*
C10	−0.0087 (3)	0.70801 (17)	1.1286 (4)	0.0379 (8)
H10	−0.0445	0.7404	1.1888	0.046*
C11	−0.0501 (3)	0.64453 (16)	1.1177 (4)	0.0301 (7)
H11	−0.1149	0.6338	1.1695	0.036*
C12	0.0021 (3)	0.59713 (15)	1.0324 (4)	0.0276 (7)
H12	−0.0275	0.5541	1.0259	0.033*
C13	0.0974 (3)	0.61137 (18)	0.9557 (4)	0.0328 (8)
C14	0.2369 (2)	0.46740 (14)	0.5998 (3)	0.0221 (6)
C15	0.2486 (3)	0.39870 (15)	0.5978 (4)	0.0254 (6)
H15	0.3033	0.3785	0.6708	0.030*
C16	0.1821 (3)	0.36033 (15)	0.4920 (4)	0.0290 (7)
H16	0.1905	0.3141	0.4952	0.035*
C17	0.1030 (3)	0.38830 (16)	0.3805 (4)	0.0323 (7)
H17	0.0570	0.3616	0.3087	0.039*
C18	0.0928 (3)	0.45473 (15)	0.3762 (4)	0.0275 (7)
H18	0.0396	0.4739	0.2991	0.033*
C19	0.1585 (2)	0.49587 (15)	0.4825 (4)	0.0254 (6)
C20	0.1448 (3)	0.56547 (15)	0.4608 (4)	0.0275 (7)
H20	0.0919	0.5791	0.3755	0.033*
C21	0.4254 (3)	0.52192 (16)	1.3198 (4)	0.0309 (7)
H21A	0.4975	0.5112	1.2809	0.046*
H21B	0.4061	0.4891	1.4000	0.046*
H21C	0.4290	0.5652	1.3714	0.046*
C22	0.3339 (3)	0.43848 (16)	1.0928 (4)	0.0366 (8)
H22A	0.2918	0.4313	0.9869	0.055*
H22B	0.3040	0.4106	1.1761	0.055*
H22C	0.4117	0.4275	1.0837	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0292 (3)	0.0240 (3)	0.0256 (2)	0.0075 (2)	−0.00755 (19)	−0.00551 (19)
S1	0.0237 (4)	0.0383 (5)	0.0260 (4)	0.0052 (3)	−0.0018 (3)	0.0021 (3)
O1	0.0367 (14)	0.0310 (13)	0.0459 (14)	−0.0077 (10)	−0.0096 (11)	0.0101 (11)
O2	0.0291 (13)	0.0813 (19)	0.0271 (12)	0.0156 (13)	−0.0029 (10)	−0.0159 (12)
O3	0.0278 (12)	0.0252 (11)	0.0238 (10)	0.0042 (9)	−0.0050 (9)	−0.0033 (9)
O4	0.0339 (13)	0.0264 (11)	0.0289 (11)	0.0063 (9)	−0.0068 (10)	−0.0033 (9)
O5	0.0288 (12)	0.0290 (12)	0.0263 (11)	−0.0001 (9)	−0.0053 (9)	−0.0003 (9)
N1'	0.018 (5)	0.020 (6)	0.017 (4)	−0.005 (4)	0.000 (3)	−0.002 (3)
N1	0.020 (3)	0.024 (3)	0.022 (2)	0.0037 (19)	−0.0026 (18)	0.0012 (18)
C1	0.0342 (19)	0.0320 (18)	0.0221 (15)	−0.0041 (14)	−0.0114 (13)	0.0061 (13)
C2	0.0267 (17)	0.041 (2)	0.0258 (15)	0.0085 (14)	0.0014 (13)	0.0022 (14)
C3	0.0267 (17)	0.052 (2)	0.0297 (17)	−0.0045 (16)	0.0018 (14)	0.0147 (15)
C4	0.034 (2)	0.0310 (19)	0.047 (2)	−0.0034 (15)	−0.0108 (16)	0.0073 (15)
C5	0.0338 (19)	0.040 (2)	0.0355 (18)	0.0106 (16)	−0.0096 (15)	−0.0066 (15)
C6	0.0201 (15)	0.052 (2)	0.0190 (14)	−0.0005 (14)	−0.0039 (12)	0.0046 (14)
C7'	0.015 (5)	0.028 (7)	0.017 (4)	0.000 (4)	0.001 (4)	−0.002 (4)
C7	0.026 (3)	0.023 (3)	0.025 (3)	0.001 (2)	−0.008 (2)	−0.003 (2)
C8	0.0242 (18)	0.074 (3)	0.0207 (15)	−0.0046 (17)	−0.0028 (13)	0.0137 (16)
C9	0.053 (2)	0.037 (2)	0.042 (2)	−0.0202 (18)	−0.0217 (18)	0.0140 (17)
C10	0.044 (2)	0.0325 (19)	0.0352 (18)	0.0054 (16)	−0.0078 (16)	−0.0029 (15)
C11	0.0250 (17)	0.0375 (19)	0.0279 (16)	0.0003 (14)	0.0034 (13)	0.0034 (14)
C12	0.0290 (17)	0.0267 (17)	0.0265 (15)	0.0031 (13)	−0.0011 (13)	0.0006 (13)
C13	0.0226 (16)	0.054 (2)	0.0206 (15)	0.0101 (15)	−0.0063 (12)	0.0003 (14)
C14	0.0194 (15)	0.0271 (16)	0.0202 (13)	−0.0017 (12)	0.0052 (11)	0.0007 (12)
C15	0.0221 (15)	0.0292 (17)	0.0250 (15)	0.0023 (12)	0.0021 (12)	−0.0003 (12)
C16	0.0313 (17)	0.0251 (16)	0.0308 (16)	−0.0016 (13)	0.0031 (14)	−0.0017 (13)
C17	0.0288 (18)	0.0367 (19)	0.0304 (17)	−0.0054 (14)	−0.0039 (14)	−0.0052 (14)
C18	0.0204 (16)	0.0353 (18)	0.0264 (15)	0.0007 (13)	−0.0005 (12)	−0.0009 (13)
C19	0.0228 (16)	0.0305 (17)	0.0226 (14)	0.0031 (13)	−0.0001 (12)	0.0007 (12)
C20	0.0254 (17)	0.0318 (17)	0.0246 (15)	0.0061 (13)	−0.0019 (13)	−0.0001 (13)
C21	0.0265 (17)	0.0408 (19)	0.0245 (15)	0.0059 (14)	−0.0031 (13)	0.0011 (14)
C22	0.042 (2)	0.0310 (18)	0.0348 (18)	−0.0077 (15)	−0.0090 (15)	0.0037 (14)

Geometric parameters (Å, º) top

Mn1—O1	1.878 (2)	C7'—H7'	0.9500
Mn1—O2	1.899 (3)	C7—H7	0.9500
Mn1—O3	1.905 (2)	C8—C9	1.396 (5)
Mn1—N1	1.986 (5)	C8—C13	1.401 (5)
Mn1—N1'	2.094 (11)	C9—C10	1.374 (5)
Mn1—O5	2.177 (2)	C9—H9	0.9500
Mn1—O4	2.267 (2)	C10—C11	1.390 (5)
S1—O5	1.520 (2)	C10—H10	0.9500
S1—C21	1.782 (3)	C11—C12	1.377 (4)
S1—C22	1.785 (3)	C11—H11	0.9500
O1—C1	1.322 (4)	C12—C13	1.391 (5)
O2—C13	1.336 (4)	C12—H12	0.9500
O3—C14	1.312 (3)	C14—C15	1.410 (4)
O4—C20	1.233 (4)	C14—C19	1.419 (4)
N1'—C7'	1.299 (19)	C15—C16	1.378 (4)
N1'—C6	1.492 (11)	C15—H15	0.9500
N1—C7	1.285 (11)	C16—C17	1.391 (4)
N1—C8	1.478 (6)	C16—H16	0.9500
C1—C2	1.399 (4)	C17—C18	1.362 (5)
C1—C6	1.414 (5)	C17—H17	0.9500
C2—C3	1.375 (5)	C18—C19	1.408 (4)
C2—H2	0.9500	C18—H18	0.9500
C3—C4	1.388 (5)	C19—C20	1.440 (4)
C3—H3	0.9500	C20—H20	0.9500
C4—C5	1.362 (5)	C21—H21A	0.9800
C4—H4	0.9500	C21—H21B	0.9800
C5—C6	1.393 (5)	C21—H21C	0.9800
C5—H5	0.9500	C22—H22A	0.9800
C6—C7	1.443 (7)	C22—H22B	0.9800
C7'—C8	1.478 (11)	C22—H22C	0.9800

O1—Mn1—O2	175.43 (11)	C8—C7'—H7'	122.9
O1—Mn1—O3	92.60 (10)	N1—C7—C6	121.1 (7)
O2—Mn1—O3	91.96 (11)	N1—C7—H7	119.4
O1—Mn1—N1	97.47 (19)	C6—C7—H7	119.4
O2—Mn1—N1	77.96 (19)	C9—C8—C13	120.8 (3)
O3—Mn1—N1	168.85 (17)	C9—C8—C7'	96.8 (5)
O1—Mn1—N1'	72.5 (3)	C13—C8—C7'	142.4 (6)
O2—Mn1—N1'	103.0 (3)	C9—C8—N1	135.8 (4)
O3—Mn1—N1'	162.8 (3)	C13—C8—N1	103.4 (4)
N1—Mn1—N1'	25.3 (2)	C10—C9—C8	120.1 (3)
O1—Mn1—O5	89.25 (9)	C10—C9—H9	119.9
O2—Mn1—O5	90.97 (9)	C8—C9—H9	119.9
O3—Mn1—O5	90.93 (8)	C9—C10—C11	119.4 (3)
N1—Mn1—O5	93.96 (12)	C9—C10—H10	120.3
N1'—Mn1—O5	97.3 (2)	C11—C10—H10	120.3
O1—Mn1—O4	89.92 (9)	C12—C11—C10	120.7 (3)
O2—Mn1—O4	90.13 (9)	C12—C11—H11	119.7
O3—Mn1—O4	85.72 (8)	C10—C11—H11	119.7
N1—Mn1—O4	89.50 (12)	C11—C12—C13	121.0 (3)
N1'—Mn1—O4	85.7 (2)	C11—C12—H12	119.5
O5—Mn1—O4	176.51 (8)	C13—C12—H12	119.5
O5—S1—C21	104.34 (14)	O2—C13—C12	121.2 (3)
O5—S1—C22	105.36 (15)	O2—C13—C8	120.8 (3)
C21—S1—C22	98.00 (16)	C12—C13—C8	118.0 (3)
C1—O1—Mn1	124.3 (2)	O3—C14—C15	118.2 (3)
C13—O2—Mn1	118.3 (2)	O3—C14—C19	124.2 (3)
C14—O3—Mn1	129.96 (19)	C15—C14—C19	117.5 (3)
C20—O4—Mn1	120.4 (2)	C16—C15—C14	121.2 (3)
S1—O5—Mn1	122.20 (12)	C16—C15—H15	119.4
C7'—N1'—C6	117.5 (11)	C14—C15—H15	119.4
C7'—N1'—Mn1	120.2 (9)	C15—C16—C17	121.0 (3)
C6—N1'—Mn1	122.3 (7)	C15—C16—H16	119.5
C7—N1—C8	117.6 (6)	C17—C16—H16	119.5
C7—N1—Mn1	123.4 (5)	C18—C17—C16	118.8 (3)
C8—N1—Mn1	118.9 (4)	C18—C17—H17	120.6
O1—C1—C2	119.7 (3)	C16—C17—H17	120.6
O1—C1—C6	122.1 (3)	C17—C18—C19	122.2 (3)
C2—C1—C6	118.1 (3)	C17—C18—H18	118.9
C3—C2—C1	120.6 (3)	C19—C18—H18	118.9
C3—C2—H2	119.7	C18—C19—C14	119.1 (3)
C1—C2—H2	119.7	C18—C19—C20	117.3 (3)
C2—C3—C4	121.1 (3)	C14—C19—C20	123.5 (3)
C2—C3—H3	119.4	O4—C20—C19	127.3 (3)
C4—C3—H3	119.4	O4—C20—H20	116.4
C5—C4—C3	119.1 (3)	C19—C20—H20	116.4
C5—C4—H4	120.4	S1—C21—H21A	109.5
C3—C4—H4	120.4	S1—C21—H21B	109.5
C4—C5—C6	121.5 (3)	H21A—C21—H21B	109.5
C4—C5—H5	119.3	S1—C21—H21C	109.5
C6—C5—H5	119.3	H21A—C21—H21C	109.5
C5—C6—C1	119.6 (3)	H21B—C21—H21C	109.5
C5—C6—C7	110.1 (4)	S1—C22—H22A	109.5
C1—C6—C7	130.3 (4)	S1—C22—H22B	109.5
C5—C6—N1'	142.3 (5)	H22A—C22—H22B	109.5
C1—C6—N1'	98.1 (5)	S1—C22—H22C	109.5
N1'—C7'—C8	114.2 (11)	H22A—C22—H22C	109.5
N1'—C7'—H7'	122.9	H22B—C22—H22C	109.5

O3—Mn1—O1—C1	164.1 (2)	C4—C5—C6—N1'	−179.3 (5)
N1—Mn1—O1—C1	−11.1 (3)	O1—C1—C6—C5	−177.5 (3)
N1'—Mn1—O1—C1	−7.2 (3)	C2—C1—C6—C5	2.1 (4)
O5—Mn1—O1—C1	−105.0 (2)	O1—C1—C6—C7	5.0 (5)
O4—Mn1—O1—C1	78.4 (2)	C2—C1—C6—C7	−175.4 (3)
O3—Mn1—O2—C13	177.8 (2)	O1—C1—C6—N1'	1.2 (4)
N1—Mn1—O2—C13	−7.1 (2)	C2—C1—C6—N1'	−179.2 (4)
N1'—Mn1—O2—C13	−10.9 (3)	C7'—N1'—C6—C5	−11.1 (10)
O5—Mn1—O2—C13	86.8 (2)	Mn1—N1'—C6—C5	171.2 (4)
O4—Mn1—O2—C13	−96.5 (2)	C7'—N1'—C6—C1	170.8 (6)
O1—Mn1—O3—C14	−120.6 (2)	Mn1—N1'—C6—C1	−7.0 (5)
O2—Mn1—O3—C14	59.1 (2)	C7'—N1'—C6—C7	−3.8 (5)
N1—Mn1—O3—C14	34.0 (8)	Mn1—N1'—C6—C7	178.4 (9)
N1'—Mn1—O3—C14	−91.2 (8)	C6—N1'—C7'—C8	178.6 (5)
O5—Mn1—O3—C14	150.1 (2)	Mn1—N1'—C7'—C8	−3.5 (9)
O4—Mn1—O3—C14	−30.8 (2)	C8—N1—C7—C6	179.2 (3)
O1—Mn1—O4—C20	120.4 (2)	Mn1—N1—C7—C6	−3.8 (6)
O2—Mn1—O4—C20	−64.2 (2)	C5—C6—C7—N1	176.5 (4)
O3—Mn1—O4—C20	27.8 (2)	C1—C6—C7—N1	−5.8 (6)
N1—Mn1—O4—C20	−142.1 (3)	N1'—C6—C7—N1	1.2 (5)
N1'—Mn1—O4—C20	−167.2 (4)	N1'—C7'—C8—C9	177.8 (6)
C21—S1—O5—Mn1	−173.72 (14)	N1'—C7'—C8—C13	−5.7 (11)
C22—S1—O5—Mn1	83.62 (17)	N1'—C7'—C8—N1	1.6 (5)
O1—Mn1—O5—S1	−170.71 (15)	C7—N1—C8—C9	−9.2 (6)
O2—Mn1—O5—S1	13.85 (16)	Mn1—N1—C8—C9	173.6 (3)
O3—Mn1—O5—S1	−78.12 (15)	C7—N1—C8—C13	171.5 (4)
N1—Mn1—O5—S1	91.8 (2)	Mn1—N1—C8—C13	−5.6 (3)
N1'—Mn1—O5—S1	117.1 (3)	C7—N1—C8—C7'	−3.9 (6)
O1—Mn1—N1'—C7'	−169.6 (7)	Mn1—N1—C8—C7'	178.9 (6)
O2—Mn1—N1'—C7'	9.9 (6)	C13—C8—C9—C10	−0.5 (5)
O3—Mn1—N1'—C7'	159.4 (6)	C7'—C8—C9—C10	176.9 (4)
N1—Mn1—N1'—C7'	1.1 (5)	N1—C8—C9—C10	−179.7 (4)
O5—Mn1—N1'—C7'	−82.8 (6)	C8—C9—C10—C11	−0.7 (5)
O4—Mn1—N1'—C7'	99.1 (6)	C9—C10—C11—C12	0.8 (5)
O1—Mn1—N1'—C6	8.1 (4)	C10—C11—C12—C13	0.2 (5)
O2—Mn1—N1'—C6	−172.3 (4)	Mn1—O2—C13—C12	−174.9 (2)
O3—Mn1—N1'—C6	−22.9 (11)	Mn1—O2—C13—C8	6.3 (4)
N1—Mn1—N1'—C6	178.8 (9)	C11—C12—C13—O2	179.8 (3)
O5—Mn1—N1'—C6	95.0 (5)	C11—C12—C13—C8	−1.4 (4)
O4—Mn1—N1'—C6	−83.2 (5)	C9—C8—C13—O2	−179.6 (3)
O1—Mn1—N1—C7	10.2 (4)	C7'—C8—C13—O2	4.4 (8)
O2—Mn1—N1—C7	−169.9 (4)	N1—C8—C13—O2	−0.3 (4)
O3—Mn1—N1—C7	−144.2 (7)	C9—C8—C13—C12	1.6 (5)
N1'—Mn1—N1—C7	1.3 (5)	C7'—C8—C13—C12	−174.4 (6)
O5—Mn1—N1—C7	100.0 (4)	N1—C8—C13—C12	−179.1 (3)
O4—Mn1—N1—C7	−79.6 (4)	Mn1—O3—C14—C15	−160.1 (2)
O1—Mn1—N1—C8	−172.8 (3)	Mn1—O3—C14—C19	22.4 (4)
O2—Mn1—N1—C8	7.1 (2)	O3—C14—C15—C16	178.8 (3)
O3—Mn1—N1—C8	32.8 (9)	C19—C14—C15—C16	−3.5 (4)
N1'—Mn1—N1—C8	178.3 (7)	C14—C15—C16—C17	1.6 (5)
O5—Mn1—N1—C8	−83.0 (3)	C15—C16—C17—C18	0.7 (5)
O4—Mn1—N1—C8	97.4 (3)	C16—C17—C18—C19	−0.9 (5)
Mn1—O1—C1—C2	−173.8 (2)	C17—C18—C19—C14	−1.0 (5)
Mn1—O1—C1—C6	5.8 (4)	C17—C18—C19—C20	176.6 (3)
O1—C1—C2—C3	178.4 (3)	O3—C14—C19—C18	−179.3 (3)
C6—C1—C2—C3	−1.3 (4)	C15—C14—C19—C18	3.2 (4)
C1—C2—C3—C4	−0.3 (5)	O3—C14—C19—C20	3.2 (5)
C2—C3—C4—C5	1.1 (5)	C15—C14—C19—C20	−174.3 (3)
C3—C4—C5—C6	−0.2 (5)	Mn1—O4—C20—C19	−17.4 (4)
C4—C5—C6—C1	−1.4 (5)	C18—C19—C20—O4	180.0 (3)
C4—C5—C6—C7	176.6 (3)	C14—C19—C20—O4	−2.5 (5)

Experimental details

Crystal data
Chemical formula	[Mn(C₁₃H₉NO₂)(C₇H₅O₂)(C₂H₆OS)]
M_r	465.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.1342 (3), 20.4224 (5), 8.1812 (2)
β (°)	94.692 (2)
V (Å³)	2020.59 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.79
Crystal size (mm)	0.15 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (TWINABS; Bruker, 2009)
T_min, T_max	0.891, 0.925
No. of measured, independent and observed [I > 2σ(I)] reflections	39957, 5025, 3528
R_int	0.091
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.129, 1.03
No. of reflections	5025
No. of parameters	293
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.49

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank the University of Malaya (grant No. RG020/09AFR) for supporting this study.

References

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