Chlorido[2,2'-[1,2-phenyl-enebis(nitrilo-methanylyl-idyne)]diphenolato-κ(4) O,N,N',O']manganese(III) methanol monosolvate.

In the title complex, [Mn(C20H14N2O2)Cl]·CH3OH, the central Mn(III) atom displays a distorted square-pyramidal coordination by two N and two O atoms from the tetradentate 2,2'-[1,2-phenyl-enebis(nitrilo-methanylyl-idyne)]diphenolate ligand and one chloride ligand. The Mn(III) atom is 0.525 (4) Å out of the square basal N2O2 least-squares plane. The complex mol-ecule is hydrogen bonded to the methanol solvent mol-ecule.

Related literature

For background to manganese and manganese–salen complexes, see: Law et al. (1998 ▶); Lenoble et al. (1998 ▶); Horner et al. (1999 ▶); Asada et al. (2000 ▶); Dubois et al. (2003 ▶); Gultneh et al. (2003 ▶); Mitra et al. (2006 ▶). For related structures, see: Pecoraro & Butler (1986 ▶); Dang et al. (2005 ▶); Martínez et al. (2002 ▶); Panja et al. (2003 ▶).

Experimental

Crystal data

[Mn(C20H14N2O2)Cl]·CH4O

M = 436.76

Triclinic,

a = 7.4251 (2) Å

b = 9.8341 (2) Å

c = 13.3035 (3) Å

α = 78.803 (1)°

β = 83.305 (2)°

γ = 86.344 (2)°

V = 945.58 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.87 mm−1

T = 296 K

0.24 × 0.17 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.819, T max = 0.896

17011 measured reflections

4302 independent reflections

3311 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.086

S = 1.02

4302 reflections

255 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813016450/vn2073sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016450/vn2073Isup2.hkl

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

[Mn(C20H14N2O2)Cl]·CH4O	Z = 2
Mr = 436.76	F(000) = 448
Triclinic, P1	Dx = 1.534 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4251 (2) Å	Cell parameters from 5729 reflections
b = 9.8341 (2) Å	θ = 2.4–26.8°
c = 13.3035 (3) Å	µ = 0.87 mm−1
α = 78.803 (1)°	T = 296 K
β = 83.305 (2)°	Block, pink
γ = 86.344 (2)°	0.24 × 0.17 × 0.13 mm
V = 945.58 (4) Å3

Bruker SMART APEXII CCD area-detector diffractometer	4302 independent reflections
Radiation source: fine-focus sealed tube	3311 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
phi and ω scans	θmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.819, Tmax = 0.896	k = −12→12
17011 measured reflections	l = −17→17

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0419P)2 + 0.2015P] where P = (Fo2 + 2Fc2)/3
4302 reflections	(Δ/σ)max = 0.001
255 parameters	Δρmax = 0.33 e Å−3
1 restraint	Δρmin = −0.40 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.06050 (4)	0.87475 (3)	0.26112 (2)	0.03227 (10)
Cl1	0.30457 (9)	0.81214 (7)	0.34473 (5)	0.06368 (18)
N1	0.1304 (2)	1.06118 (16)	0.16224 (12)	0.0368 (4)
N2	−0.0670 (2)	1.02686 (16)	0.33991 (11)	0.0345 (4)
O1	0.0801 (2)	0.79008 (14)	0.14311 (10)	0.0475 (4)
O2	−0.1221 (2)	0.75440 (15)	0.32907 (11)	0.0522 (4)
C1	0.1710 (3)	0.8242 (2)	0.05065 (14)	0.0388 (4)
C2	0.2021 (3)	0.7250 (2)	−0.01285 (16)	0.0479 (5)
H2	0.1588	0.6364	0.0104	0.057*
C3	0.2960 (3)	0.7574 (3)	−0.10922 (17)	0.0535 (6)
H3	0.3169	0.6897	−0.1498	0.064*
C4	0.3601 (3)	0.8889 (3)	−0.14702 (17)	0.0537 (6)
H4	0.4250	0.9092	−0.2119	0.064*
C5	0.3266 (3)	0.9881 (2)	−0.08765 (16)	0.0477 (5)
H5	0.3662	1.0772	−0.1136	0.057*
C6	0.2334 (3)	0.9589 (2)	0.01207 (14)	0.0383 (4)
C7	0.2019 (3)	1.0706 (2)	0.06718 (15)	0.0394 (4)
H7	0.2356	1.1580	0.0320	0.047*
C8	0.1020 (3)	1.18087 (19)	0.20795 (14)	0.0358 (4)
C9	0.1713 (3)	1.3105 (2)	0.16491 (16)	0.0453 (5)
H9	0.2440	1.3228	0.1023	0.054*
C10	0.1317 (3)	1.4201 (2)	0.21548 (17)	0.0485 (5)
H10	0.1778	1.5064	0.1867	0.058*
C11	0.0245 (3)	1.4028 (2)	0.30831 (18)	0.0482 (5)
H11	−0.0018	1.4779	0.3414	0.058*
C12	−0.0441 (3)	1.2757 (2)	0.35271 (16)	0.0433 (5)
H12	−0.1157	1.2648	0.4157	0.052*
C13	−0.0057 (3)	1.16326 (19)	0.30263 (14)	0.0344 (4)
C14	−0.1822 (3)	1.0000 (2)	0.42216 (14)	0.0369 (4)
H14	−0.2217	1.0734	0.4551	0.044*
C15	−0.2531 (3)	0.8672 (2)	0.46599 (14)	0.0367 (4)
C16	−0.3650 (3)	0.8553 (2)	0.56071 (15)	0.0427 (5)
H16	−0.3912	0.9332	0.5906	0.051*
C17	−0.4353 (3)	0.7316 (2)	0.60900 (16)	0.0486 (5)
H17	−0.5095	0.7254	0.6709	0.058*
C18	−0.3944 (3)	0.6145 (2)	0.56445 (17)	0.0507 (6)
H18	−0.4384	0.5293	0.5982	0.061*
C19	−0.2902 (3)	0.6237 (2)	0.47166 (17)	0.0501 (5)
H19	−0.2670	0.5449	0.4425	0.060*
C20	−0.2181 (3)	0.7492 (2)	0.41977 (15)	0.0395 (5)
C1S	0.6113 (4)	0.6064 (3)	0.1772 (3)	0.0922 (10)
H1S1	0.6377	0.5284	0.2298	0.138*
H1S2	0.5154	0.5847	0.1411	0.138*
H1S3	0.5742	0.6855	0.2081	0.138*
O1S	0.7639 (3)	0.6357 (2)	0.10906 (15)	0.0848 (6)
H1S	0.8457 (10)	0.6671 (4)	0.1397 (4)	0.127*

	U11	U22	U33	U12	U13	U23
Mn1	0.04290 (19)	0.02961 (15)	0.02400 (15)	−0.00218 (12)	0.00435 (11)	−0.00877 (11)
Cl1	0.0695 (4)	0.0623 (4)	0.0640 (4)	0.0191 (3)	−0.0223 (3)	−0.0216 (3)
N1	0.0434 (9)	0.0363 (8)	0.0313 (8)	−0.0010 (7)	−0.0008 (7)	−0.0095 (7)
N2	0.0406 (9)	0.0335 (8)	0.0296 (8)	0.0000 (7)	−0.0012 (7)	−0.0082 (7)
O1	0.0711 (10)	0.0413 (8)	0.0303 (7)	−0.0094 (7)	0.0070 (7)	−0.0124 (6)
O2	0.0673 (10)	0.0460 (8)	0.0445 (8)	−0.0185 (7)	0.0193 (7)	−0.0215 (7)
C1	0.0462 (12)	0.0448 (11)	0.0256 (9)	0.0027 (9)	−0.0009 (8)	−0.0105 (8)
C2	0.0654 (15)	0.0439 (12)	0.0346 (11)	0.0005 (10)	0.0002 (10)	−0.0125 (9)
C3	0.0662 (15)	0.0590 (14)	0.0373 (11)	0.0093 (12)	0.0022 (10)	−0.0224 (11)
C4	0.0579 (14)	0.0696 (16)	0.0329 (11)	−0.0013 (12)	0.0084 (10)	−0.0159 (11)
C5	0.0521 (13)	0.0557 (13)	0.0346 (11)	−0.0075 (10)	0.0048 (9)	−0.0105 (10)
C6	0.0409 (11)	0.0442 (11)	0.0302 (10)	−0.0005 (9)	−0.0001 (8)	−0.0104 (8)
C7	0.0453 (12)	0.0397 (10)	0.0319 (10)	−0.0054 (9)	0.0019 (8)	−0.0062 (8)
C8	0.0445 (11)	0.0316 (9)	0.0318 (10)	0.0000 (8)	−0.0047 (8)	−0.0074 (8)
C9	0.0592 (14)	0.0397 (11)	0.0355 (11)	−0.0066 (10)	0.0010 (10)	−0.0056 (9)
C10	0.0626 (14)	0.0335 (10)	0.0486 (13)	−0.0058 (10)	−0.0052 (11)	−0.0046 (9)
C11	0.0559 (14)	0.0359 (11)	0.0550 (13)	0.0026 (10)	−0.0020 (11)	−0.0175 (10)
C12	0.0477 (12)	0.0402 (11)	0.0426 (12)	0.0033 (9)	0.0008 (9)	−0.0144 (9)
C13	0.0387 (11)	0.0314 (9)	0.0333 (10)	0.0018 (8)	−0.0039 (8)	−0.0080 (8)
C14	0.0405 (11)	0.0390 (10)	0.0318 (10)	0.0024 (8)	0.0004 (8)	−0.0121 (8)
C15	0.0368 (11)	0.0409 (10)	0.0331 (10)	−0.0011 (8)	−0.0009 (8)	−0.0107 (8)
C16	0.0448 (12)	0.0473 (12)	0.0353 (10)	−0.0006 (9)	0.0057 (9)	−0.0131 (9)
C17	0.0493 (13)	0.0600 (14)	0.0351 (11)	−0.0083 (11)	0.0084 (9)	−0.0113 (10)
C18	0.0568 (14)	0.0497 (13)	0.0438 (12)	−0.0178 (11)	0.0059 (10)	−0.0060 (10)
C19	0.0570 (14)	0.0461 (12)	0.0493 (13)	−0.0142 (10)	0.0095 (11)	−0.0192 (10)
C20	0.0409 (11)	0.0437 (11)	0.0345 (10)	−0.0069 (9)	0.0039 (8)	−0.0117 (9)
C1S	0.093 (2)	0.077 (2)	0.100 (2)	−0.0166 (18)	0.029 (2)	−0.0218 (18)
O1S	0.0820 (14)	0.1037 (16)	0.0640 (12)	−0.0195 (12)	0.0008 (11)	−0.0039 (11)

Mn1—O2	1.8868 (14)	C9—C10	1.377 (3)
Mn1—O1	1.9022 (13)	C9—H9	0.9300
Mn1—N1	2.0944 (16)	C10—C11	1.376 (3)
Mn1—N2	2.1047 (15)	C10—H10	0.9300
Mn1—Cl1	2.2277 (7)	C11—C12	1.377 (3)
N1—C7	1.302 (2)	C11—H11	0.9300
N1—C8	1.420 (2)	C12—C13	1.396 (3)
N2—C14	1.303 (2)	C12—H12	0.9300
N2—C13	1.421 (2)	C14—C15	1.429 (3)
O1—C1	1.325 (2)	C14—H14	0.9300
O2—C20	1.321 (2)	C15—C20	1.412 (3)
C1—C2	1.402 (3)	C15—C16	1.415 (3)
C1—C6	1.411 (3)	C16—C17	1.365 (3)
C2—C3	1.376 (3)	C16—H16	0.9300
C2—H2	0.9300	C17—C18	1.395 (3)
C3—C4	1.387 (3)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.369 (3)
C4—C5	1.364 (3)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.398 (3)
C5—C6	1.409 (3)	C19—H19	0.9300
C5—H5	0.9300	C1S—O1S	1.374 (3)
C6—C7	1.428 (3)	C1S—H1S1	0.9600
C7—H7	0.9300	C1S—H1S2	0.9600
C8—C9	1.396 (3)	C1S—H1S3	0.9600
C8—C13	1.398 (3)	O1S—H1S	0.8725
O2—Mn1—O1	91.47 (6)	C10—C9—H9	120.1
O2—Mn1—N1	148.62 (7)	C8—C9—H9	120.1
O1—Mn1—N1	87.98 (6)	C11—C10—C9	120.50 (19)
O2—Mn1—N2	87.70 (6)	C11—C10—H10	119.8
O1—Mn1—N2	148.11 (7)	C9—C10—H10	119.8
N1—Mn1—N2	76.74 (6)	C10—C11—C12	120.75 (19)
O2—Mn1—Cl1	105.95 (6)	C10—C11—H11	119.6
O1—Mn1—Cl1	108.96 (5)	C12—C11—H11	119.6
N1—Mn1—Cl1	103.86 (5)	C11—C12—C13	119.64 (19)
N2—Mn1—Cl1	101.87 (5)	C11—C12—H12	120.2
C7—N1—C8	120.67 (16)	C13—C12—H12	120.2
C7—N1—Mn1	124.46 (13)	C12—C13—C8	119.69 (17)
C8—N1—Mn1	114.81 (12)	C12—C13—N2	125.41 (18)
C14—N2—C13	120.85 (16)	C8—C13—N2	114.90 (16)
C14—N2—Mn1	124.04 (13)	N2—C14—C15	125.47 (18)
C13—N2—Mn1	114.86 (12)	N2—C14—H14	117.3
C1—O1—Mn1	131.49 (12)	C15—C14—H14	117.3
C20—O2—Mn1	130.62 (12)	C20—C15—C16	118.96 (18)
O1—C1—C2	119.31 (18)	C20—C15—C14	123.61 (17)
O1—C1—C6	122.27 (17)	C16—C15—C14	117.43 (17)
C2—C1—C6	118.39 (18)	C17—C16—C15	121.27 (19)
C3—C2—C1	120.6 (2)	C17—C16—H16	119.4
C3—C2—H2	119.7	C15—C16—H16	119.4
C1—C2—H2	119.7	C16—C17—C18	119.27 (19)
C2—C3—C4	121.3 (2)	C16—C17—H17	120.4
C2—C3—H3	119.4	C18—C17—H17	120.4
C4—C3—H3	119.4	C19—C18—C17	120.7 (2)
C5—C4—C3	119.0 (2)	C19—C18—H18	119.6
C5—C4—H4	120.5	C17—C18—H18	119.6
C3—C4—H4	120.5	C18—C19—C20	121.3 (2)
C4—C5—C6	121.6 (2)	C18—C19—H19	119.3
C4—C5—H5	119.2	C20—C19—H19	119.3
C6—C5—H5	119.2	O2—C20—C19	119.40 (18)
C5—C6—C1	119.06 (18)	O2—C20—C15	122.20 (17)
C5—C6—C7	117.27 (18)	C19—C20—C15	118.39 (18)
C1—C6—C7	123.63 (17)	O1S—C1S—H1S1	109.5
N1—C7—C6	125.92 (18)	O1S—C1S—H1S2	109.5
N1—C7—H7	117.0	H1S1—C1S—H1S2	109.5
C6—C7—H7	117.0	O1S—C1S—H1S3	109.5
C9—C8—C13	119.60 (17)	H1S1—C1S—H1S3	109.5
C9—C8—N1	124.94 (18)	H1S2—C1S—H1S3	109.5
C13—C8—N1	115.45 (16)	C1S—O1S—H1S	109.5
C10—C9—C8	119.82 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1S—H1S···O1i	0.87	2.19	2.999 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1S—H1S⋯O1i	0.87	2.19	2.999 (3)	154

Symmetry code: (i) .