Literature DB >> 21754686

Triaqua-bis-{2-meth-oxy-6-[(phenyl-iminium-yl)meth-yl]phenolate-κO}manganese(II) dinitrate.

Guo-Di Ge, Jin-Bei Shen, Guo-Liang Zhao.

Abstract

The crystal structure of the title compound, [Mn(C(14)H(13)NO(2))(2)(H(2)O)(3)](NO(3))(2), is comprised of two Schiff base 2-meth-oxy-6-(N-phenyl-carboximido-yl)phenol (HL) ligands and three coordinated water mol-ecules. The Mn(II) ion lies on a twofold axis that bis-ects one water O atom. The coordination sphere of the five-coordinate Mn atom is completed by the two monodentate HL ligands and three coordinated water mol-ecules binding through their O atoms, affording a distorted tetra-gonal-pyramidal geometry. In the phenolate ligands, the hy-droxy H atom transfers to the imine N atom. This H atom is also involved in an intra-molecular N-H⋯O hydrogen bond that imposes a nearly planar conformation on each ligand, with dihedral angles of 2.78 (3) and 2.43 (5)° between the aromatic rings of each ligand. In the crystal, mol-ecules are linked by inter-molecular O-H⋯O hydrogen bonds.

Entities: CellLine Chemical Disease Gene Species

Year: 2011 PMID： 21754686 PMCID： PMC3120327 DOI： 10.1107/S1600536811019593

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For Schiff base ligands derived from o-vanillin and aniline and their rare earth complexes, see: Garnovskii et al. (1993 ▶); Shen et al. (2011 ▶); Zhao et al. (2006 ▶). For the synthesis of related Schiff bases, see: Burrows & Bailar (1966 ▶).

Experimental

Crystal data

[Mn(C14H13NO2)2(H2O)3](NO3)2 M = 687.52 Orthorhombic, a = 17.4364 (3) Å b = 10.4199 (2) Å c = 16.9014 (3) Å V = 3070.74 (10) Å3 Z = 4 Mo Kα radiation μ = 0.50 mm−1 T = 296 K 0.26 × 0.14 × 0.06 mm

Data collection

Bruker APEXII area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.918, T max = 0.969 11534 measured reflections 2705 independent reflections 1864 reflections with I > 2σ(I) R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.118 S = 1.07 2705 reflections 210 parameters 4 restraints H-atom parameters constrained Δρmax = 0.22 e Å−3 Δρmin = −0.33 e Å−3 Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); 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: SHELXL97. Crystal structure: contains datablocks global. DOI: 10.1107/S1600536811019593/rn2084sup1.cif Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Mn(C₁₄H₁₃NO₂)₂(H₂O)₃](NO₃)₂	F(000) = 1428
M_r = 687.52	D_x = 1.487 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2780 reflections
a = 17.4364 (3) Å	θ = 2.3–25.0°
b = 10.4199 (2) Å	µ = 0.50 mm⁻¹
c = 16.9014 (3) Å	T = 296 K
V = 3070.74 (10) Å³	Block, red
Z = 4	0.26 × 0.14 × 0.06 mm

Bruker APEXII area-detector diffractometer	2705 independent reflections
Radiation source: fine-focus sealed tube	1864 reflections with I > 2σ(I)
graphite	R_int = 0.035
φ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→20
T_min = 0.918, T_max = 0.969	k = −12→12
11534 measured reflections	l = −19→20

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0599P)²] where P = (F_o² + 2F_c²)/3
2705 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.22 e Å⁻³
4 restraints	Δρ_min = −0.33 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
Mn1	0.5000	0.33828 (5)	0.2500	0.0421 (2)
O1	0.38704 (9)	0.30891 (16)	0.29244 (10)	0.0460 (5)
O1W	0.46876 (11)	0.3817 (2)	0.12448 (11)	0.0662 (6)
H1WA	0.4674	0.3323	0.0845	0.099*
H1WB	0.4722	0.4555	0.1034	0.099*
O2	0.43669 (10)	0.13545 (17)	0.19361 (11)	0.0597 (6)
O2W	0.5000	0.5493 (2)	0.2500	0.0604 (8)
H2WA	0.5076	0.6037	0.2134	0.091*
N1	0.27417 (11)	0.4077 (2)	0.37372 (11)	0.0414 (5)
H1A	0.3225	0.4015	0.3645	0.050*
C1	0.15746 (18)	0.6407 (3)	0.48555 (17)	0.0601 (8)
H1	0.1066	0.6663	0.4902	0.072*
C2	0.2127 (2)	0.7023 (3)	0.52808 (17)	0.0611 (8)
H2	0.1996	0.7697	0.5615	0.073*
C3	0.28780 (19)	0.6644 (3)	0.52134 (17)	0.0606 (8)
H3	0.3255	0.7060	0.5507	0.073*
C4	0.30785 (16)	0.5658 (3)	0.47178 (15)	0.0518 (7)
H4	0.3588	0.5402	0.4678	0.062*
C5	0.25210 (14)	0.5048 (2)	0.42797 (14)	0.0404 (6)
C6	0.17617 (15)	0.5410 (3)	0.43588 (16)	0.0532 (7)
H6	0.1381	0.4982	0.4078	0.064*
C7	0.23079 (14)	0.3276 (2)	0.33641 (15)	0.0418 (6)
H7	0.1785	0.3294	0.3470	0.050*
C8	0.25749 (14)	0.2381 (2)	0.28081 (14)	0.0395 (6)
C9	0.33671 (14)	0.2317 (2)	0.26127 (14)	0.0394 (6)
C10	0.35947 (15)	0.1353 (2)	0.20736 (15)	0.0436 (6)
C11	0.30689 (17)	0.0538 (2)	0.17469 (16)	0.0536 (7)
H11	0.3233	−0.0087	0.1393	0.064*
C12	0.22898 (16)	0.0622 (3)	0.19330 (16)	0.0533 (7)
H12	0.1941	0.0060	0.1703	0.064*
C13	0.20462 (16)	0.1525 (3)	0.24499 (15)	0.0479 (7)
H13	0.1527	0.1585	0.2572	0.057*
C14	0.46842 (18)	0.0327 (3)	0.1474 (2)	0.0848 (11)
H14A	0.5233	0.0405	0.1460	0.102*
H14B	0.4485	0.0369	0.0945	0.102*
H14C	0.4547	−0.0481	0.1708	0.102*
O5	0.03646 (13)	0.2937 (2)	0.48143 (13)	0.0812 (7)
O3	0.04351 (13)	0.2360 (2)	0.36037 (13)	0.0807 (7)
O4	−0.02028 (16)	0.1259 (2)	0.44494 (15)	0.0969 (8)
N3	0.02000 (14)	0.2189 (3)	0.42868 (17)	0.0580 (6)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0316 (4)	0.0502 (4)	0.0447 (4)	0.000	0.0042 (2)	0.000
O1	0.0337 (10)	0.0565 (11)	0.0479 (11)	−0.0064 (9)	0.0031 (9)	−0.0088 (9)
O1W	0.0830 (14)	0.0674 (13)	0.0484 (11)	0.0038 (12)	−0.0137 (11)	−0.0008 (11)
O2	0.0445 (12)	0.0622 (12)	0.0725 (13)	0.0052 (9)	0.0152 (10)	−0.0130 (11)
O2W	0.080 (2)	0.0509 (17)	0.0506 (16)	0.000	0.0063 (14)	0.000
N1	0.0292 (11)	0.0542 (13)	0.0408 (12)	0.0027 (10)	0.0044 (10)	0.0003 (11)
C1	0.057 (2)	0.0640 (19)	0.0593 (19)	0.0149 (16)	0.0125 (16)	−0.0020 (17)
C2	0.086 (3)	0.0493 (17)	0.0481 (18)	0.0032 (17)	0.0109 (17)	−0.0025 (15)
C3	0.072 (2)	0.0544 (17)	0.0554 (19)	−0.0096 (16)	−0.0029 (16)	−0.0059 (16)
C4	0.0437 (17)	0.0572 (17)	0.0545 (17)	−0.0043 (14)	−0.0016 (14)	−0.0017 (15)
C5	0.0382 (15)	0.0468 (14)	0.0363 (14)	0.0017 (12)	0.0056 (12)	0.0064 (13)
C6	0.0425 (17)	0.0627 (18)	0.0545 (16)	0.0024 (14)	−0.0021 (14)	−0.0039 (16)
C7	0.0298 (14)	0.0500 (14)	0.0458 (14)	−0.0028 (12)	0.0012 (11)	0.0035 (11)
C8	0.0338 (15)	0.0449 (14)	0.0397 (13)	−0.0032 (11)	−0.0004 (11)	0.0058 (11)
C9	0.0375 (15)	0.0440 (15)	0.0367 (14)	−0.0011 (13)	0.0002 (12)	0.0054 (12)
C10	0.0432 (17)	0.0434 (15)	0.0441 (16)	0.0031 (13)	0.0052 (13)	0.0026 (13)
C11	0.070 (2)	0.0427 (16)	0.0477 (17)	−0.0044 (15)	0.0059 (15)	−0.0051 (14)
C12	0.0534 (19)	0.0541 (17)	0.0525 (17)	−0.0150 (14)	−0.0026 (15)	0.0015 (16)
C13	0.0366 (16)	0.0565 (17)	0.0505 (17)	−0.0084 (13)	0.0004 (12)	0.0025 (15)
C14	0.072 (2)	0.082 (2)	0.101 (3)	0.014 (2)	0.027 (2)	−0.027 (2)
O5	0.0847 (17)	0.0844 (16)	0.0745 (15)	0.0036 (13)	−0.0044 (13)	−0.0299 (14)
O3	0.0851 (17)	0.0974 (18)	0.0595 (13)	−0.0022 (14)	0.0156 (13)	−0.0015 (14)
O4	0.128 (2)	0.0688 (15)	0.0942 (19)	−0.0224 (15)	0.0255 (17)	−0.0070 (15)
N3	0.0543 (16)	0.0531 (16)	0.0666 (17)	0.0138 (13)	0.0033 (14)	−0.0050 (17)

Mn1—O1	2.1184 (16)	C3—H3	0.9300
Mn1—O1ⁱ	2.1184 (16)	C4—C5	1.377 (3)
Mn1—O2W	2.199 (3)	C4—H4	0.9300
Mn1—O1W	2.2365 (18)	C5—C6	1.383 (3)
Mn1—O1Wⁱ	2.2366 (18)	C6—H6	0.9300
Mn1—O2	2.5678 (19)	C7—C8	1.403 (3)
Mn1—O2ⁱ	2.5678 (19)	C7—H7	0.9300
O1—C9	1.302 (3)	C8—C13	1.419 (3)
O1W—H1WA	0.8500	C8—C9	1.422 (3)
O1W—H1WB	0.8501	C9—C10	1.413 (3)
O2—C10	1.366 (3)	C10—C11	1.366 (3)
O2—C14	1.436 (3)	C11—C12	1.397 (4)
O2W—H2WA	0.8500	C11—H11	0.9300
N1—C7	1.291 (3)	C12—C13	1.352 (4)
N1—C5	1.419 (3)	C12—H12	0.9300
N1—H1A	0.8600	C13—H13	0.9300
C1—C2	1.363 (4)	C14—H14A	0.9600
C1—C6	1.375 (3)	C14—H14B	0.9600
C1—H1	0.9300	C14—H14C	0.9600
C2—C3	1.372 (4)	O5—N3	1.218 (3)
C2—H2	0.9300	O3—N3	1.238 (3)
C3—C4	1.371 (4)	O4—N3	1.228 (3)

O1—Mn1—O1ⁱ	163.38 (9)	C2—C3—H3	119.7
O1—Mn1—O2W	98.31 (5)	C3—C4—C5	119.6 (3)
O1ⁱ—Mn1—O2W	98.31 (5)	C3—C4—H4	120.2
O1—Mn1—O1W	97.12 (7)	C5—C4—H4	120.2
O1ⁱ—Mn1—O1W	86.24 (7)	C4—C5—C6	119.9 (3)
O2W—Mn1—O1W	78.33 (5)	C4—C5—N1	119.0 (2)
O1—Mn1—O1Wⁱ	86.24 (7)	C6—C5—N1	121.1 (2)
O1ⁱ—Mn1—O1Wⁱ	97.12 (7)	C1—C6—C5	119.5 (3)
O2W—Mn1—O1Wⁱ	78.33 (5)	C1—C6—H6	120.3
O1W—Mn1—O1Wⁱ	156.67 (11)	C5—C6—H6	120.3
O1—Mn1—O2	66.86 (6)	N1—C7—C8	124.2 (2)
O1ⁱ—Mn1—O2	98.93 (6)	N1—C7—H7	117.9
O2W—Mn1—O2	145.39 (4)	C8—C7—H7	117.9
O1W—Mn1—O2	73.12 (7)	C7—C8—C13	119.2 (2)
O1Wⁱ—Mn1—O2	128.55 (7)	C7—C8—C9	120.6 (2)
O1—Mn1—O2ⁱ	98.93 (6)	C13—C8—C9	120.2 (2)
O1ⁱ—Mn1—O2ⁱ	66.86 (6)	O1—C9—C10	120.7 (2)
O2W—Mn1—O2ⁱ	145.39 (4)	O1—C9—C8	122.1 (2)
O1W—Mn1—O2ⁱ	128.55 (7)	C10—C9—C8	117.1 (2)
O1Wⁱ—Mn1—O2ⁱ	73.12 (7)	C11—C10—O2	126.4 (2)
O2—Mn1—O2ⁱ	69.21 (8)	C11—C10—C9	120.9 (2)
C9—O1—Mn1	125.39 (15)	O2—C10—C9	112.7 (2)
Mn1—O1W—H1WA	129.7	C10—C11—C12	121.5 (2)
Mn1—O1W—H1WB	124.3	C10—C11—H11	119.3
H1WA—O1W—H1WB	102.5	C12—C11—H11	119.3
C10—O2—C14	118.1 (2)	C13—C12—C11	119.6 (3)
C10—O2—Mn1	111.19 (15)	C13—C12—H12	120.2
C14—O2—Mn1	130.53 (16)	C11—C12—H12	120.2
Mn1—O2W—H2WA	131.8	C12—C13—C8	120.6 (3)
C7—N1—C5	128.2 (2)	C12—C13—H13	119.7
C7—N1—H1A	116.0	C8—C13—H13	119.7
C5—N1—H1A	115.9	O2—C14—H14A	109.5
C2—C1—C6	120.7 (3)	O2—C14—H14B	109.5
C2—C1—H1	119.7	H14A—C14—H14B	109.5
C6—C1—H1	119.7	O2—C14—H14C	109.5
C1—C2—C3	119.7 (3)	H14A—C14—H14C	109.5
C1—C2—H2	120.2	H14B—C14—H14C	109.5
C3—C2—H2	120.2	O5—N3—O4	118.4 (3)
C4—C3—C2	120.6 (3)	O5—N3—O3	120.8 (3)
C4—C3—H3	119.7	O4—N3—O3	120.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O5ⁱⁱ	0.85	2.18	3.032 (3)	180
O1W—H1WB···O4ⁱⁱⁱ	0.85	1.96	2.809 (3)	180
O2W—H2WA···O3ⁱⁱⁱ	0.85	1.96	2.800 (3)	169
N1—H1A···O1	0.86	1.92	2.611 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O5ⁱ	0.85	2.18	3.032 (3)	180
O1W—H1WB⋯O4ⁱⁱ	0.85	1.96	2.809 (3)	180
O2W—H2WA⋯O3ⁱⁱ	0.85	1.96	2.800 (3)	169
N1—H1A⋯O1	0.86	1.92	2.611 (2)	137

Symmetry codes: (i) ; (ii) .

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Bis[2-meth-oxy-6-(phenyl-iminiomethyl)phenolate-κO,O']bis-(thio-cyanato-κN)manganese(II).

Authors: Jin-Bei Shen; Guo-Di Ge; Guo-Liang Zhao
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-03-19

2 in total