Bis[4-(2-hydroxy-benzyl-ideneamino)benzoato-κO]tetrakis-(methanol-κO)manganese(II).

In the title mononuclear complex, [Mn(C(14)H(10)NO(3))(2)(CH(3)OH)(4)], the Mn(II) atom, lying on an inversion centre, exhibits a distorted octa-hedral geometry, defined by two O atoms from two monodentate ligands and four O atoms from four methanol mol-ecules. The crystal structure involves intra-molecular O-H⋯N and O-H⋯O and inter-molecular O-H⋯O hydrogen bonds.

Related literature

For general background, see: Deeth (2008 ▶); Dubois et al. (2008 ▶); Huang et al. (2004 ▶).

Experimental

Crystal data

[Mn(C14H10NO3)2(CH4O)4]

M = 663.57

Monoclinic,

a = 15.0341 (6) Å

b = 11.8819 (4) Å

c = 8.8178 (3) Å

β = 98.912 (4)°

V = 1556.14 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.49 mm−1

T = 293 K

0.6 × 0.6 × 0.3 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.823, T max = 1.000 (expected range = 0.711–0.865)

10167 measured reflections

3374 independent reflections

2008 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.102

S = 0.92

3374 reflections

205 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S160053680901681X/hy2192sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901681X/hy2192Isup2.hkl

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

[Mn(C14H10NO3)2(CH4O)4]	F(000) = 694
Mr = 663.57	Dx = 1.416 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3622 reflections
a = 15.0341 (6) Å	θ = 2.7–29.8°
b = 11.8819 (4) Å	µ = 0.49 mm−1
c = 8.8178 (3) Å	T = 293 K
β = 98.912 (4)°	Block, colorless
V = 1556.14 (10) Å3	0.6 × 0.6 × 0.3 mm
Z = 2

Oxford Diffraction Gemini S Ultra diffractometer	3374 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2008 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 16.0855 pixels mm-1	θmax = 27.0°, θmin = 2.7°
ω scans	h = −19→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −15→14
Tmin = 0.823, Tmax = 1.000	l = −11→11
10167 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 0.92	w = 1/[σ2(Fo2) + (0.058P)2] where P = (Fo2 + 2Fc2)/3
3374 reflections	(Δ/σ)max < 0.001
205 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

	x	y	z	Uiso*/Ueq
Mn1	0.5000	0.0000	0.0000	0.02171 (15)
O1	1.09324 (11)	0.03911 (14)	0.80222 (19)	0.0404 (4)
H1A	1.0420	0.0210	0.7533	0.048*
O2	0.57922 (10)	−0.20216 (13)	0.26345 (18)	0.0350 (4)
O3	0.60735 (10)	−0.03061 (12)	0.18268 (17)	0.0291 (4)
N1	0.94227 (12)	−0.06941 (15)	0.7155 (2)	0.0295 (5)
C1	1.11213 (15)	−0.0410 (2)	0.9117 (3)	0.0303 (6)
C2	1.19528 (16)	−0.0391 (2)	1.0049 (3)	0.0360 (6)
H2A	1.2378	0.0151	0.9904	0.043*
C3	1.21437 (16)	−0.1187 (2)	1.1196 (3)	0.0397 (6)
H3A	1.2704	−0.1177	1.1815	0.048*
C4	1.15283 (15)	−0.1989 (2)	1.1442 (3)	0.0377 (6)
H4A	1.1665	−0.2511	1.2229	0.045*
C5	1.07051 (15)	−0.2014 (2)	1.0510 (3)	0.0332 (6)
H5A	1.0288	−0.2561	1.0675	0.040*
C6	1.04831 (14)	−0.12450 (18)	0.9335 (2)	0.0276 (5)
C7	0.96278 (15)	−0.13309 (19)	0.8321 (3)	0.0306 (5)
H7A	0.9215	−0.1870	0.8529	0.037*
C8	0.86185 (14)	−0.08573 (19)	0.6112 (2)	0.0269 (5)
C9	0.81878 (14)	−0.18938 (19)	0.5844 (3)	0.0312 (6)
H9A	0.8412	−0.2524	0.6402	0.037*
C10	0.74265 (14)	−0.19842 (19)	0.4748 (3)	0.0299 (5)
H10A	0.7137	−0.2675	0.4587	0.036*
C11	0.70884 (14)	−0.10594 (17)	0.3887 (2)	0.0225 (5)
C12	0.75350 (15)	−0.00380 (18)	0.4146 (2)	0.0259 (5)
H12A	0.7322	0.0587	0.3567	0.031*
C13	0.82848 (15)	0.00641 (19)	0.5241 (2)	0.0279 (5)
H13A	0.8572	0.0757	0.5401	0.033*
C14	0.62646 (14)	−0.11436 (18)	0.2699 (2)	0.0234 (5)
O4	0.42496 (10)	0.08439 (12)	0.16313 (16)	0.0306 (4)
H4B	0.4371	0.1543	0.1666	0.037*
O5	0.43893 (10)	−0.15779 (11)	0.05698 (16)	0.0271 (4)
H5B	0.4791	−0.1938	0.1163	0.033*
C15	0.42208 (19)	0.0436 (2)	0.3134 (3)	0.0436 (7)
H15A	0.3862	0.0932	0.3650	0.065*
H15B	0.4821	0.0403	0.3695	0.065*
H15C	0.3960	−0.0303	0.3075	0.065*
C16	0.39223 (16)	−0.23800 (19)	−0.0468 (3)	0.0368 (6)
H16A	0.3730	−0.2999	0.0103	0.055*
H16B	0.4316	−0.2651	−0.1145	0.055*
H16C	0.3406	−0.2029	−0.1058	0.055*

	U11	U22	U33	U12	U13	U23
Mn1	0.0265 (3)	0.0162 (2)	0.0218 (3)	−0.0006 (2)	0.00172 (19)	0.0002 (2)
O1	0.0353 (10)	0.0405 (10)	0.0447 (11)	−0.0090 (8)	0.0041 (8)	0.0001 (9)
O2	0.0365 (9)	0.0240 (9)	0.0407 (10)	−0.0064 (7)	−0.0061 (8)	0.0091 (8)
O3	0.0313 (9)	0.0259 (9)	0.0282 (9)	−0.0022 (7)	−0.0011 (7)	0.0067 (7)
N1	0.0296 (11)	0.0303 (11)	0.0282 (10)	−0.0001 (9)	0.0029 (9)	−0.0037 (9)
C1	0.0333 (14)	0.0307 (13)	0.0272 (12)	0.0057 (10)	0.0061 (11)	−0.0047 (11)
C2	0.0260 (13)	0.0373 (14)	0.0454 (15)	−0.0033 (11)	0.0077 (12)	−0.0122 (12)
C3	0.0247 (14)	0.0523 (17)	0.0392 (15)	0.0064 (12)	−0.0040 (11)	−0.0083 (13)
C4	0.0366 (14)	0.0417 (15)	0.0331 (14)	0.0070 (12)	0.0002 (12)	0.0001 (12)
C5	0.0286 (13)	0.0352 (14)	0.0354 (14)	−0.0022 (11)	0.0035 (11)	−0.0022 (12)
C6	0.0223 (12)	0.0336 (13)	0.0271 (12)	0.0010 (10)	0.0044 (10)	−0.0069 (11)
C7	0.0304 (13)	0.0313 (13)	0.0302 (13)	−0.0033 (10)	0.0053 (11)	−0.0027 (11)
C8	0.0245 (12)	0.0312 (13)	0.0249 (12)	−0.0004 (10)	0.0036 (10)	−0.0059 (10)
C9	0.0293 (13)	0.0247 (13)	0.0373 (14)	0.0055 (10)	−0.0015 (11)	0.0034 (11)
C10	0.0293 (13)	0.0226 (12)	0.0355 (14)	−0.0011 (10)	−0.0022 (11)	−0.0010 (11)
C11	0.0252 (12)	0.0214 (11)	0.0225 (11)	0.0003 (9)	0.0086 (10)	−0.0014 (9)
C12	0.0330 (12)	0.0224 (11)	0.0223 (11)	0.0000 (11)	0.0043 (9)	0.0032 (10)
C13	0.0336 (13)	0.0244 (12)	0.0251 (11)	−0.0048 (11)	0.0025 (10)	−0.0020 (11)
C14	0.0276 (12)	0.0201 (12)	0.0237 (11)	0.0025 (10)	0.0075 (10)	−0.0001 (10)
O4	0.0433 (10)	0.0183 (8)	0.0317 (9)	0.0003 (7)	0.0105 (7)	−0.0017 (7)
O5	0.0306 (8)	0.0180 (8)	0.0309 (9)	−0.0023 (7)	−0.0010 (7)	0.0019 (7)
C15	0.070 (2)	0.0313 (13)	0.0339 (14)	−0.0014 (13)	0.0207 (14)	0.0006 (12)
C16	0.0417 (15)	0.0264 (13)	0.0415 (15)	−0.0077 (11)	0.0041 (12)	−0.0096 (11)

Mn1—O3	2.1275 (15)	C7—H7A	0.9300
Mn1—O3i	2.1275 (15)	C8—C13	1.386 (3)
Mn1—O5i	2.1802 (13)	C8—C9	1.394 (3)
Mn1—O5	2.1803 (13)	C9—C10	1.383 (3)
Mn1—O4	2.2023 (14)	C9—H9A	0.9300
Mn1—O4i	2.2023 (14)	C10—C11	1.387 (3)
O1—C1	1.354 (3)	C10—H10A	0.9300
O1—H1A	0.8500	C11—C12	1.389 (3)
O2—C14	1.258 (2)	C11—C14	1.496 (3)
O3—C14	1.263 (2)	C12—C13	1.372 (3)
N1—C7	1.275 (3)	C12—H12A	0.9300
N1—C8	1.415 (3)	C13—H13A	0.9300
C1—C2	1.386 (3)	O4—C15	1.418 (3)
C1—C6	1.414 (3)	O4—H4B	0.8500
C2—C3	1.382 (3)	O5—C16	1.428 (2)
C2—H2A	0.9300	O5—H5B	0.8500
C3—C4	1.369 (3)	C15—H15A	0.9600
C3—H3A	0.9300	C15—H15B	0.9600
C4—C5	1.376 (3)	C15—H15C	0.9600
C4—H4A	0.9300	C16—H16A	0.9600
C5—C6	1.383 (3)	C16—H16B	0.9600
C5—H5A	0.9300	C16—H16C	0.9600
C6—C7	1.452 (3)
O3—Mn1—O3i	180.00 (10)	C13—C8—C9	119.0 (2)
O3—Mn1—O5i	91.39 (5)	C13—C8—N1	116.85 (19)
O3i—Mn1—O5i	88.61 (5)	C9—C8—N1	124.0 (2)
O3—Mn1—O5	88.61 (5)	C10—C9—C8	120.0 (2)
O3i—Mn1—O5	91.39 (5)	C10—C9—H9A	120.0
O5i—Mn1—O5	180.00 (7)	C8—C9—H9A	120.0
O3—Mn1—O4	89.34 (6)	C9—C10—C11	121.0 (2)
O3i—Mn1—O4	90.66 (6)	C9—C10—H10A	119.5
O5i—Mn1—O4	92.04 (5)	C11—C10—H10A	119.5
O5—Mn1—O4	87.96 (5)	C10—C11—C12	118.4 (2)
O3—Mn1—O4i	90.66 (6)	C10—C11—C14	121.60 (19)
O3i—Mn1—O4i	89.34 (6)	C12—C11—C14	120.02 (19)
O5i—Mn1—O4i	87.96 (5)	C13—C12—C11	121.1 (2)
O5—Mn1—O4i	92.04 (5)	C13—C12—H12A	119.4
O4—Mn1—O4i	180.00 (7)	C11—C12—H12A	119.4
C1—O1—H1A	104.9	C12—C13—C8	120.5 (2)
C14—O3—Mn1	132.05 (14)	C12—C13—H13A	119.7
C7—N1—C8	121.23 (19)	C8—C13—H13A	119.7
O1—C1—C2	118.8 (2)	O2—C14—O3	123.5 (2)
O1—C1—C6	121.2 (2)	O2—C14—C11	119.14 (19)
C2—C1—C6	120.0 (2)	O3—C14—C11	117.32 (18)
C3—C2—C1	119.3 (2)	C15—O4—Mn1	123.20 (14)
C3—C2—H2A	120.4	C15—O4—H4B	109.7
C1—C2—H2A	120.4	Mn1—O4—H4B	109.9
C4—C3—C2	121.6 (2)	C16—O5—Mn1	127.52 (13)
C4—C3—H3A	119.2	C16—O5—H5B	106.9
C2—C3—H3A	119.2	Mn1—O5—H5B	106.9
C3—C4—C5	119.2 (2)	O4—C15—H15A	109.5
C3—C4—H4A	120.4	O4—C15—H15B	109.5
C5—C4—H4A	120.4	H15A—C15—H15B	109.5
C4—C5—C6	121.6 (2)	O4—C15—H15C	109.5
C4—C5—H5A	119.2	H15A—C15—H15C	109.5
C6—C5—H5A	119.2	H15B—C15—H15C	109.5
C5—C6—C1	118.4 (2)	O5—C16—H16A	109.5
C5—C6—C7	120.2 (2)	O5—C16—H16B	109.5
C1—C6—C7	121.4 (2)	H16A—C16—H16B	109.5
N1—C7—C6	122.4 (2)	O5—C16—H16C	109.5
N1—C7—H7A	118.8	H16A—C16—H16C	109.5
C6—C7—H7A	118.8	H16B—C16—H16C	109.5
O5i—Mn1—O3—C14	−173.33 (18)	C8—C9—C10—C11	1.0 (3)
O5—Mn1—O3—C14	6.67 (18)	C9—C10—C11—C12	0.3 (3)
O4—Mn1—O3—C14	94.64 (19)	C9—C10—C11—C14	−179.90 (18)
O4i—Mn1—O3—C14	−85.36 (19)	C10—C11—C12—C13	−1.0 (3)
O1—C1—C2—C3	178.3 (2)	C14—C11—C12—C13	179.17 (18)
C6—C1—C2—C3	−0.6 (3)	C11—C12—C13—C8	0.4 (3)
C1—C2—C3—C4	−0.5 (4)	C9—C8—C13—C12	0.8 (3)
C2—C3—C4—C5	1.0 (4)	N1—C8—C13—C12	176.55 (18)
C3—C4—C5—C6	−0.2 (3)	Mn1—O3—C14—O2	−1.2 (3)
C4—C5—C6—C1	−0.9 (3)	Mn1—O3—C14—C11	−179.75 (12)
C4—C5—C6—C7	176.7 (2)	C10—C11—C14—O2	10.7 (3)
O1—C1—C6—C5	−177.6 (2)	C12—C11—C14—O2	−169.4 (2)
C2—C1—C6—C5	1.3 (3)	C10—C11—C14—O3	−170.6 (2)
O1—C1—C6—C7	4.8 (3)	C12—C11—C14—O3	9.2 (3)
C2—C1—C6—C7	−176.2 (2)	O3—Mn1—O4—C15	−41.12 (17)
C8—N1—C7—C6	174.53 (19)	O3i—Mn1—O4—C15	138.88 (17)
C5—C6—C7—N1	−174.7 (2)	O5i—Mn1—O4—C15	−132.49 (17)
C1—C6—C7—N1	2.8 (3)	O5—Mn1—O4—C15	47.51 (17)
C7—N1—C8—C13	157.1 (2)	O3—Mn1—O5—C16	−142.12 (16)
C7—N1—C8—C9	−27.4 (3)	O3i—Mn1—O5—C16	37.88 (16)
C13—C8—C9—C10	−1.5 (3)	O4—Mn1—O5—C16	128.49 (16)
N1—C8—C9—C10	−176.92 (19)	O4i—Mn1—O5—C16	−51.51 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.85	1.83	2.619 (2)	153
O4—H4B···O2ii	0.85	1.84	2.621 (2)	151
O5—H5B···O2	0.85	1.83	2.618 (2)	153

Table 1

Selected bond lengths (Å)

Mn1—O3	2.1275 (15)
Mn1—O5	2.1803 (13)
Mn1—O4	2.2023 (14)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.85	1.83	2.619 (2)	153
O4—H4B⋯O2i	0.85	1.84	2.621 (2)	151
O5—H5B⋯O2	0.85	1.83	2.618 (2)	153

Symmetry code: (i) .