Triaqua­chlorido[3-dimethyl­amino-1-(2-pyrid­yl)prop-2-en-1-one-κN1]manganese(II) chloride

Chu, Z.-L.

doi:10.1107/S1600536809024192

metal-organic compounds

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Volume 65| Part 8| August 2009| Page m855

doi:10.1107/S1600536809024192

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Triaquachlorido[3-dimethylamino-1-(2-pyridyl)prop-2-en-1-one-κN¹]manganese(II) chloride

Zhao-Lian Chu ^a ^*

^aSchool of Chemistry and Chemical Engineering, Anhui University of Technology, Maanshan 243002, People's Republic of China
^*Correspondence e-mail: zlchu@ahut.edu.cn

(Received 20 June 2009; accepted 24 June 2009; online 1 July 2009)

In the title compound, [MnCl(C₁₀H₁₂N₂O)(H₂O)₃]Cl, the Mn^II ion has a distorted octahedral coordination environment formed by one N and one O atom from the chelating 3-dimethylamino-1-(2-pyridyl)prop-2-en-1-one ligand, one chloride anion and three coordinated water molecules. Intermolecular O—H⋯O and O—H⋯Cl hydrogen bonds link the cations and anions into layers parallel to the ac plane.

Related literature

For the crystal structure of a related Cd(II) complex, see: Dong et al. (2009 ). For details of the synthesis, see: Sun et al. (2008 ).

Experimental

Crystal data

[MnCl(C₁₀H₁₂N₂O)(H₂O)₃]Cl
M_r = 356.10
Triclinic, $[P \overline 1]$
a = 8.7039 (17) Å
b = 9.3247 (18) Å
c = 10.1407 (19) Å
α = 98.029 (4)°
β = 98.036 (4)°
γ = 107.357 (3)°
V = 763.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.22 mm⁻¹
T = 291 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.710, T_max = 0.792
3838 measured reflections
2647 independent reflections
1898 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.096
S = 0.90
2647 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯Cl1ⁱ	0.85	2.58	3.142 (3)	125
O2—H2C⋯Cl2	0.85	2.64	3.188 (3)	124
O3—H3B⋯Cl2ⁱⁱ	0.85	2.46	3.228 (3)	150
O3—H3C⋯Cl2ⁱⁱⁱ	0.85	2.48	3.090 (3)	129
O4—H4B⋯O1ⁱⁱ	0.85	2.27	2.659 (3)	108
O4—H4C⋯Cl2	0.85	2.41	3.063 (3)	134
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+1, -z+1; (iii) x-1, y, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024192/cv2579sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809024192/cv2579Isup2.hkl

checkCIF report

Comment top

We have taken many efforts on synthesizing new ligands with pyridyl group and reported a monomeric Cd (II) complex using 3-dimethylamino-1-(4-pyridyl-)prop-2-en-1-one as ligand (Dong et al., 2009). Here we obtain an analogous ligand, 3-dimethylamino-1-(2-pyridyl-)prop-2-en-1-one by similar method, and report a new Mn (II) complex, viz. the title compound, [Mn(C₁₀H₁₂N₂O)(H₂O)₃Cl]⁺.Cl^- (I).

In (I) (Fig. 1), the Mn^II center shows an octahedral coordination geometry formed by NO₄Cl. Cholride anions are involved in formation of O—H···Cl hydrogen bonds (Table 1), which link cations and anions into layers parallel to ac plane along with the intermolecular O—H···O hydrogen bonds (Table 1).

Related literature top

For the crystal structure of the related Cd(II) complex, see: Dong et al. (2009). For details of the synthesis, see: Sun et al. (2008).

Experimental top

Ligand was prepared following the procedure reported in the literature (Sun et al., 2008). A solution of the ligand (0.1 mmol) and MnCl₂ (0.1 mmol) in 40 ml of methanol was refluxed for 2 h, and then cooled to room temperature and filtered. Single crystals suittable for X-ray analysis were grown from the methanol solution by slow evaporation at room temperature in air. Anal. Calcd. for C₁₀H₁₈MnN₂O₄Cl₂: C, 33.72; H, 5.09; N, 7.87. Found: C, 33.68; H, 5.13; N, 7.83.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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: publCIF (Westrip, 2009).

Figures top

Fig. 1. View of (I) showing 30% probability displacement ellipsoids and the atomic numbering.

Triaquachlorido[3-dimethylamino-1-(2-pyridyl)prop-2-en-1-one- κN¹]manganese(II) chloride top

Crystal data top

[MnCl(C₁₀H₁₂N₂O)(H₂O)₃]Cl	Z = 2
M_r = 356.10	F(000) = 366
Triclinic, P1	D_x = 1.549 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7039 (17) Å	Cell parameters from 956 reflections
b = 9.3247 (18) Å	θ = 2.3–27.9°
c = 10.1407 (19) Å	µ = 1.22 mm⁻¹
α = 98.029 (4)°	T = 291 K
β = 98.036 (4)°	Block, colourless
γ = 107.357 (3)°	0.30 × 0.20 × 0.20 mm
V = 763.4 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2647 independent reflections
Radiation source: fine-focus sealed tube	1898 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→10
T_min = 0.710, T_max = 0.792	k = −10→11
3838 measured reflections	l = −12→7

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.0358P)²] where P = (F_o² + 2F_c²)/3
2647 reflections	(Δ/σ)_max < 0.001
174 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[MnCl(C₁₀H₁₂N₂O)(H₂O)₃]Cl	γ = 107.357 (3)°
M_r = 356.10	V = 763.4 (3) Å³
Triclinic, P1	Z = 2
a = 8.7039 (17) Å	Mo Kα radiation
b = 9.3247 (18) Å	µ = 1.22 mm⁻¹
c = 10.1407 (19) Å	T = 291 K
α = 98.029 (4)°	0.30 × 0.20 × 0.20 mm
β = 98.036 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2647 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1898 reflections with I > 2σ(I)
T_min = 0.710, T_max = 0.792	R_int = 0.026
3838 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 0.90	Δρ_max = 0.37 e Å⁻³
2647 reflections	Δρ_min = −0.36 e Å⁻³
174 parameters

Special details top

Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses.

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	0.38327 (7)	0.51169 (6)	0.24526 (6)	0.0323 (2)
Cl1	0.18927 (14)	0.33243 (12)	0.05540 (10)	0.0480 (3)
Cl2	0.81678 (13)	0.36167 (13)	0.32531 (11)	0.0498 (3)
N1	0.3684 (4)	0.7276 (3)	0.1810 (3)	0.0331 (8)
N2	0.9228 (4)	1.0462 (4)	0.6561 (3)	0.0379 (9)
O1	0.5460 (3)	0.7046 (3)	0.4013 (2)	0.0390 (7)
O2	0.6042 (3)	0.5194 (3)	0.1505 (3)	0.0602 (9)
H2B	0.6189	0.5984	0.1148	0.072*
H2C	0.6781	0.5474	0.2219	0.072*
O3	0.1955 (3)	0.4766 (3)	0.3751 (3)	0.0536 (8)
H3B	0.2274	0.5420	0.4489	0.064*
H3C	0.1121	0.4840	0.3255	0.064*
O4	0.4698 (3)	0.3588 (3)	0.3523 (2)	0.0391 (7)
H4B	0.5335	0.4114	0.4257	0.047*
H4C	0.5278	0.3238	0.3042	0.047*
C1	0.2670 (5)	0.7350 (5)	0.0724 (4)	0.0408 (11)
H1	0.1950	0.6441	0.0189	0.049*
C2	0.2641 (5)	0.8704 (5)	0.0362 (4)	0.0471 (12)
H2A	0.1909	0.8712	−0.0396	0.056*
C3	0.3706 (5)	1.0043 (5)	0.1136 (4)	0.0481 (12)
H3A	0.3712	1.0979	0.0914	0.058*
C4	0.4769 (5)	0.9982 (4)	0.2251 (4)	0.0415 (11)
H4A	0.5509	1.0880	0.2787	0.050*
C5	0.4732 (5)	0.8596 (4)	0.2565 (4)	0.0305 (9)
C6	0.5787 (5)	0.8396 (4)	0.3796 (3)	0.0303 (9)
C7	0.7021 (5)	0.9654 (4)	0.4608 (4)	0.0325 (10)
H7	0.7174	1.0630	0.4420	0.039*
C8	0.8019 (5)	0.9433 (4)	0.5698 (4)	0.0363 (10)
H8	0.7799	0.8430	0.5831	0.044*
C9	0.9737 (6)	1.2080 (4)	0.6504 (4)	0.0541 (13)
H9A	0.9783	1.2201	0.5585	0.081*
H9B	1.0802	1.2584	0.7066	0.081*
H9C	0.8963	1.2523	0.6826	0.081*
C10	1.0158 (5)	1.0020 (5)	0.7672 (4)	0.0507 (12)
H10A	0.9657	0.8953	0.7675	0.076*
H10B	1.0157	1.0618	0.8523	0.076*
H10C	1.1267	1.0200	0.7543	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0342 (4)	0.0306 (4)	0.0272 (4)	0.0057 (3)	0.0003 (3)	0.0059 (3)
Cl1	0.0504 (7)	0.0436 (7)	0.0337 (6)	−0.0023 (5)	−0.0019 (5)	0.0035 (5)
Cl2	0.0352 (6)	0.0591 (7)	0.0507 (7)	0.0126 (6)	0.0047 (5)	0.0055 (6)
N1	0.037 (2)	0.0306 (18)	0.0264 (18)	0.0074 (16)	−0.0017 (15)	0.0038 (15)
N2	0.036 (2)	0.037 (2)	0.033 (2)	0.0064 (17)	−0.0017 (16)	0.0013 (16)
O1	0.0468 (19)	0.0289 (16)	0.0298 (16)	0.0009 (14)	−0.0060 (13)	0.0064 (12)
O2	0.052 (2)	0.088 (2)	0.0515 (19)	0.0239 (19)	0.0188 (16)	0.0382 (18)
O3	0.0363 (19)	0.077 (2)	0.0376 (18)	0.0129 (17)	0.0030 (14)	−0.0036 (15)
O4	0.0437 (18)	0.0388 (16)	0.0350 (16)	0.0152 (14)	0.0051 (13)	0.0061 (13)
C1	0.041 (3)	0.042 (3)	0.033 (2)	0.009 (2)	−0.004 (2)	0.006 (2)
C2	0.052 (3)	0.055 (3)	0.035 (3)	0.022 (3)	−0.003 (2)	0.015 (2)
C3	0.057 (3)	0.042 (3)	0.051 (3)	0.021 (2)	0.008 (2)	0.019 (2)
C4	0.050 (3)	0.030 (2)	0.039 (3)	0.007 (2)	0.003 (2)	0.008 (2)
C5	0.029 (2)	0.035 (2)	0.027 (2)	0.0113 (19)	0.0056 (17)	0.0044 (18)
C6	0.033 (2)	0.033 (2)	0.023 (2)	0.0069 (19)	0.0096 (17)	0.0018 (18)
C7	0.036 (2)	0.029 (2)	0.027 (2)	0.0060 (19)	0.0019 (18)	0.0030 (17)
C8	0.035 (3)	0.035 (2)	0.033 (2)	0.003 (2)	0.0072 (19)	0.0021 (19)
C9	0.054 (3)	0.038 (3)	0.057 (3)	0.008 (2)	−0.003 (2)	−0.001 (2)
C10	0.046 (3)	0.059 (3)	0.039 (3)	0.013 (2)	−0.007 (2)	0.007 (2)

Geometric parameters (Å, º) top

Mn1—O4	2.150 (2)	C1—H1	0.9300
Mn1—O1	2.192 (2)	C2—C3	1.366 (5)
Mn1—O3	2.217 (3)	C2—H2A	0.9300
Mn1—N1	2.234 (3)	C3—C4	1.377 (5)
Mn1—O2	2.253 (3)	C3—H3A	0.9300
Mn1—Cl1	2.4208 (11)	C4—C5	1.366 (5)
N1—C1	1.335 (4)	C4—H4A	0.9300
N1—C5	1.344 (4)	C5—C6	1.511 (5)
N2—C8	1.303 (4)	C6—C7	1.392 (5)
N2—C9	1.452 (5)	C7—C8	1.387 (5)
N2—C10	1.473 (5)	C7—H7	0.9300
O1—C6	1.263 (4)	C8—H8	0.9300
O2—H2B	0.8500	C9—H9A	0.9600
O2—H2C	0.8501	C9—H9B	0.9600
O3—H3B	0.8500	C9—H9C	0.9600
O3—H3C	0.8498	C10—H10A	0.9600
O4—H4B	0.8500	C10—H10B	0.9600
O4—H4C	0.8500	C10—H10C	0.9600
C1—C2	1.369 (5)

O4—Mn1—O1	89.04 (9)	C3—C2—C1	118.8 (4)
O4—Mn1—O3	84.40 (11)	C3—C2—H2A	120.6
O1—Mn1—O3	89.54 (10)	C1—C2—H2A	120.6
O4—Mn1—N1	160.52 (10)	C2—C3—C4	118.8 (4)
O1—Mn1—N1	72.14 (10)	C2—C3—H3A	120.6
O3—Mn1—N1	100.02 (12)	C4—C3—H3A	120.6
O4—Mn1—O2	81.56 (10)	C5—C4—C3	119.7 (4)
O1—Mn1—O2	86.99 (11)	C5—C4—H4A	120.1
O3—Mn1—O2	165.59 (10)	C3—C4—H4A	120.1
N1—Mn1—O2	92.22 (11)	N1—C5—C4	121.8 (3)
O4—Mn1—Cl1	100.99 (7)	N1—C5—C6	114.0 (3)
O1—Mn1—Cl1	169.97 (8)	C4—C5—C6	124.2 (3)
O3—Mn1—Cl1	91.26 (8)	O1—C6—C7	124.3 (3)
N1—Mn1—Cl1	97.88 (8)	O1—C6—C5	115.6 (3)
O2—Mn1—Cl1	94.59 (8)	C7—C6—C5	120.1 (3)
C1—N1—C5	118.0 (3)	C8—C7—C6	119.1 (4)
C1—N1—Mn1	125.2 (3)	C8—C7—H7	120.4
C5—N1—Mn1	116.8 (2)	C6—C7—H7	120.4
C8—N2—C9	123.4 (3)	N2—C8—C7	127.8 (4)
C8—N2—C10	120.5 (3)	N2—C8—H8	116.1
C9—N2—C10	116.1 (3)	C7—C8—H8	116.1
C6—O1—Mn1	120.2 (2)	N2—C9—H9A	109.5
Mn1—O2—H2B	103.2	N2—C9—H9B	109.5
Mn1—O2—H2C	99.5	H9A—C9—H9B	109.5
H2B—O2—H2C	104.5	N2—C9—H9C	109.5
Mn1—O3—H3B	111.7	H9A—C9—H9C	109.5
Mn1—O3—H3C	103.7	H9B—C9—H9C	109.5
H3B—O3—H3C	112.7	N2—C10—H10A	109.5
Mn1—O4—H4B	107.9	N2—C10—H10B	109.5
Mn1—O4—H4C	106.9	H10A—C10—H10B	109.5
H4B—O4—H4C	106.9	N2—C10—H10C	109.5
N1—C1—C2	123.0 (4)	H10A—C10—H10C	109.5
N1—C1—H1	118.5	H10B—C10—H10C	109.5
C2—C1—H1	118.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···Cl1ⁱ	0.85	2.58	3.142 (3)	125
O2—H2C···Cl2	0.85	2.64	3.188 (3)	124
O3—H3B···Cl2ⁱⁱ	0.85	2.46	3.228 (3)	150
O3—H3C···Cl2ⁱⁱⁱ	0.85	2.48	3.090 (3)	129
O4—H4B···O1ⁱⁱ	0.85	2.27	2.659 (3)	108
O4—H4C···Cl2	0.85	2.41	3.063 (3)	134

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

Experimental details

Crystal data
Chemical formula	[MnCl(C₁₀H₁₂N₂O)(H₂O)₃]Cl
M_r	356.10
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	8.7039 (17), 9.3247 (18), 10.1407 (19)
α, β, γ (°)	98.029 (4), 98.036 (4), 107.357 (3)
V (Å³)	763.4 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.22
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.710, 0.792
No. of measured, independent and observed [I > 2σ(I)] reflections	3838, 2647, 1898
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.096, 0.90
No. of reflections	2647
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.36

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···Cl1ⁱ	0.85	2.58	3.142 (3)	125.0
O2—H2C···Cl2	0.85	2.64	3.188 (3)	124.0
O3—H3B···Cl2ⁱⁱ	0.85	2.46	3.228 (3)	150.0
O3—H3C···Cl2ⁱⁱⁱ	0.85	2.48	3.090 (3)	129.0
O4—H4B···O1ⁱⁱ	0.85	2.27	2.659 (3)	108.0
O4—H4C···Cl2	0.85	2.41	3.063 (3)	134.0

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

Acknowledgements

The author acknowledges Anhui University of Technology for supporting of this work.

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dong, H.-Z., Chu, Z.-L. & Hu, N.-L. (2009). Acta Cryst. E65, m358. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, Y.-Y., Dong, H.-Z. & Cheng, L. (2008). Acta Cryst. E64, o901. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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