Diaqua-bis(4-chloro-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)manganese(II).

The title compound, [Mn(C(7)H(4)ClO(2))(2)(C(10)H(14)N(2)O)(2)(H(2)O)(2)], is a monomeric complex with the Mn(II) atom lying on an inversion center. It contains two 4-chloro-benzoate and two diethyl-nicotinamide ligands and two water mol-ecules, all of which are monodentate. The four O atoms in the equatorial plane around the Mn atom form a slightly distorted square-planar arrangement, while the distorted octa-hedral geometry is completed by two N atoms in the axial positions. In the crystal structure, O-H⋯O hydrogen bonds link the mol-ecules into an infinite chain.

Related literature

For general background, see: Adiwidjaja et al. (1978 ▶); Amiraslanov et al. (1979 ▶); Antolini et al. (1982 ▶); Antsyshkina et al. (1980 ▶); Nadzhafov et al. (1981 ▶); Shnulin et al. (1981 ▶). For related structures, see: Hökelek et al. (1995 ▶, 1997 ▶); Hökelek et al. (2007 ▶); Hökelek & Necefoğlu (1996 ▶, 1997 ▶, 2007 ▶).

Experimental

Crystal data

[Mn(C7H4ClO2)2(C10H14N2O)2(H2O)2]

M = 758.54

Triclinic,

a = 7.3552 (1) Å

b = 8.6465 (2) Å

c = 15.9847 (3) Å

α = 84.500 (16)°

β = 78.616 (17)°

γ = 68.154 (17)°

V = 924.73 (12) Å3

Z = 1

Mo Kα radiation

μ = 0.56 mm−1

T = 294 (2) K

0.30 × 0.15 × 0.10 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.902, T max = 0.950

4010 measured reflections

3752 independent reflections

2604 reflections with I > 2σ(I)

R int = 0.062

3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.254

S = 1.04

3752 reflections

225 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.26 e Å−3

Δρmin = −1.31 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808005540/hy2120sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005540/hy2120Isup2.hkl

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

[Mn(C7H4ClO2)2(C10H14N2O)2(H2O)2]	Z = 1
Mr = 758.54	F000 = 395
Triclinic, P1	Dx = 1.362 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.3552 (1) Å	Cell parameters from 25 reflections
b = 8.6465 (2) Å	θ = 5.2–11.6º
c = 15.9847 (3) Å	µ = 0.56 mm−1
α = 84.500 (16)º	T = 294 (2) K
β = 78.616 (17)º	Block, colorless
γ = 68.154 (17)º	0.30 × 0.15 × 0.10 mm
V = 924.73 (12) Å3

Enraf–Nonius TurboCAD-4 diffractometer	Rint = 0.062
Radiation source: fine-focus sealed tube	θmax = 26.3º
Monochromator: graphite	θmin = 3.0º
T = 294(2) K	h = −8→9
ω scans	k = 0→10
Absorption correction: ψ scan(North et al., 1968)	l = −19→19
Tmin = 0.902, Tmax = 0.950	3 standard reflections
4010 measured reflections	every 120 min
3752 independent reflections	intensity decay: 1%
2604 reflections with I > 2σ(I)

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.080	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.254	w = 1/[σ2(Fo2) + (0.1471P)2 + 1.5562P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3752 reflections	Δρmax = 1.26 e Å−3
225 parameters	Δρmin = −1.31 e Å−3
5 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
Mn	0.0000	1.0000	0.0000	0.0323 (3)
Cl	−0.7397 (3)	0.8445 (3)	0.46709 (13)	0.0925 (7)
O1	−0.1119 (5)	0.8758 (4)	0.1086 (2)	0.0408 (8)
O2	0.0744 (5)	0.8690 (5)	0.2036 (3)	0.0508 (10)
O3	−0.8388 (6)	1.3270 (5)	0.1267 (3)	0.0576 (11)
O4	−0.2247 (6)	0.9829 (5)	−0.0681 (2)	0.0463 (9)
H41	−0.195 (10)	1.042 (7)	−0.122 (2)	0.07 (2)*
H42	−0.221 (12)	0.880 (5)	−0.083 (4)	0.08 (2)*
N1	−0.2326 (6)	1.2447 (5)	0.0532 (3)	0.0360 (9)
N2	−0.8349 (8)	1.4183 (8)	0.2506 (4)	0.0649 (15)
C1	−0.0808 (7)	0.8688 (6)	0.1836 (3)	0.0366 (11)
C2	−0.2462 (7)	0.8636 (5)	0.2547 (3)	0.0350 (10)
C3	−0.4206 (7)	0.8580 (6)	0.2372 (3)	0.0381 (11)
H3	−0.4358	0.8589	0.1807	0.046*
C4	−0.5733 (8)	0.8509 (7)	0.3024 (4)	0.0487 (13)
H4	−0.6898	0.8463	0.2904	0.058*
C5	−0.5477 (9)	0.8509 (8)	0.3850 (4)	0.0525 (14)
C6	−0.3789 (9)	0.8586 (8)	0.4047 (4)	0.0533 (14)
H6	−0.3655	0.8585	0.4613	0.064*
C7	−0.2282 (8)	0.8665 (7)	0.3392 (3)	0.0434 (12)
H7	−0.1138	0.8739	0.3520	0.052*
C8	−0.2050 (7)	1.3893 (6)	0.0424 (3)	0.0390 (11)
H8	−0.0855	1.3917	0.0107	0.047*
C9	−0.3452 (8)	1.5356 (6)	0.0760 (4)	0.0461 (13)
H9	−0.3203	1.6343	0.0676	0.055*
C10	−0.5227 (8)	1.5332 (6)	0.1223 (4)	0.0442 (13)
H10	−0.6197	1.6304	0.1458	0.053*
C11	−0.5554 (7)	1.3848 (6)	0.1334 (3)	0.0359 (11)
C12	−0.4080 (7)	1.2446 (6)	0.0965 (3)	0.0380 (11)
H12	−0.4315	1.1453	0.1020	0.046*
C13	−0.7519 (7)	1.3715 (6)	0.1710 (3)	0.0413 (12)
C14	−0.7427 (13)	1.4762 (10)	0.3087 (5)	0.080 (2)
H14A	−0.6247	1.4935	0.2770	0.096*
H14B	−0.8350	1.5823	0.3318	0.096*
C15	−0.6883 (17)	1.3572 (14)	0.3785 (7)	0.132
H15A	−0.6290	1.3989	0.4151	0.132*
H15B	−0.5949	1.2527	0.3558	0.132*
H15C	−0.8052	1.3412	0.4106	0.132*
C16	−1.0402 (11)	1.4197 (10)	0.2815 (6)	0.080 (2)
H16A	−1.1031	1.4942	0.3291	0.096*
H16B	−1.1177	1.4616	0.2362	0.096*
C17	−1.0391 (16)	1.2541 (11)	0.3085 (7)	0.107 (3)
H17A	−1.1734	1.2589	0.3272	0.160*
H17B	−0.9659	1.2137	0.3546	0.160*
H17C	−0.9773	1.1802	0.2614	0.160*

	U11	U22	U33	U12	U13	U23
Mn	0.0261 (5)	0.0275 (5)	0.0373 (6)	−0.0030 (4)	−0.0004 (4)	−0.0107 (4)
Cl	0.0696 (12)	0.144 (2)	0.0638 (12)	−0.0517 (13)	0.0190 (9)	−0.0096 (12)
O1	0.043 (2)	0.0384 (19)	0.0390 (19)	−0.0133 (16)	−0.0033 (15)	−0.0072 (14)
O2	0.034 (2)	0.061 (3)	0.057 (2)	−0.0162 (18)	−0.0097 (17)	−0.0010 (19)
O3	0.043 (2)	0.066 (3)	0.070 (3)	−0.022 (2)	−0.0078 (19)	−0.022 (2)
O4	0.043 (2)	0.046 (2)	0.054 (2)	−0.0195 (17)	−0.0090 (17)	−0.0081 (18)
N1	0.030 (2)	0.026 (2)	0.046 (2)	−0.0054 (16)	−0.0002 (17)	−0.0086 (16)
N2	0.052 (3)	0.079 (4)	0.061 (3)	−0.026 (3)	0.011 (2)	−0.024 (3)
C1	0.031 (2)	0.022 (2)	0.049 (3)	−0.0010 (18)	−0.007 (2)	−0.0055 (19)
C2	0.034 (2)	0.022 (2)	0.044 (3)	−0.0032 (18)	−0.006 (2)	−0.0050 (18)
C3	0.037 (3)	0.033 (3)	0.043 (3)	−0.012 (2)	−0.007 (2)	−0.005 (2)
C4	0.036 (3)	0.058 (3)	0.055 (3)	−0.021 (3)	−0.005 (2)	−0.005 (3)
C5	0.044 (3)	0.055 (3)	0.051 (3)	−0.015 (3)	0.005 (3)	−0.005 (3)
C6	0.055 (3)	0.064 (4)	0.038 (3)	−0.018 (3)	−0.006 (2)	−0.001 (3)
C7	0.036 (3)	0.045 (3)	0.047 (3)	−0.010 (2)	−0.008 (2)	−0.008 (2)
C8	0.032 (2)	0.032 (2)	0.051 (3)	−0.009 (2)	−0.005 (2)	−0.009 (2)
C9	0.042 (3)	0.030 (3)	0.066 (4)	−0.012 (2)	−0.007 (3)	−0.009 (2)
C10	0.040 (3)	0.027 (2)	0.059 (3)	−0.003 (2)	−0.005 (2)	−0.018 (2)
C11	0.031 (2)	0.032 (2)	0.040 (3)	−0.0040 (19)	−0.0066 (19)	−0.0103 (19)
C12	0.030 (2)	0.028 (2)	0.050 (3)	−0.0054 (19)	0.000 (2)	−0.010 (2)
C13	0.031 (2)	0.038 (3)	0.051 (3)	−0.007 (2)	−0.003 (2)	−0.013 (2)
C14	0.085 (5)	0.078 (5)	0.072 (5)	−0.029 (4)	−0.002 (4)	−0.009 (4)
C15	0.180	0.156	0.138	−0.130	−0.127	0.126
C16	0.060 (4)	0.067 (5)	0.098 (6)	−0.015 (4)	0.018 (4)	−0.026 (4)
C17	0.116 (8)	0.071 (6)	0.112 (7)	−0.031 (5)	0.030 (6)	−0.014 (5)

Mn—O1i	2.141 (3)	C7—C6	1.383 (8)
Mn—O1	2.141 (3)	C7—H7	0.9300
Mn—O4	2.205 (4)	C8—H8	0.9300
Mn—O4i	2.205 (4)	C9—C8	1.376 (7)
Mn—N1i	2.281 (4)	C9—H9	0.9300
Mn—N1	2.281 (4)	C10—C9	1.373 (8)
Cl—C5	1.741 (6)	C10—H10	0.9300
O1—C1	1.256 (6)	C11—C12	1.378 (6)
O2—C1	1.245 (6)	C11—C10	1.380 (7)
O3—C13	1.214 (6)	C12—H12	0.9300
O4—H41	0.99 (4)	C13—N2	1.328 (7)
O4—H42	0.93 (5)	C13—C11	1.494 (7)
N1—C8	1.330 (6)	C14—C15	1.453 (9)
N1—C12	1.339 (6)	C14—H14A	0.9700
N2—C14	1.471 (10)	C14—H14B	0.9700
N2—C16	1.489 (9)	C15—H15A	0.9600
C2—C3	1.384 (7)	C15—H15B	0.9600
C2—C7	1.387 (7)	C15—H15C	0.9600
C2—C1	1.502 (7)	C16—C17	1.453 (11)
C3—H3	0.9300	C16—H16A	0.9700
C4—C5	1.369 (8)	C16—H16B	0.9700
C4—C3	1.388 (7)	C17—H17A	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C5—C6	1.366 (9)	C17—H17C	0.9600
C6—H6	0.9300
O1i—Mn—O1	180.000 (1)	C6—C7—H7	119.7
O1i—Mn—O4	90.38 (14)	C2—C7—H7	119.7
O1—Mn—O4	89.62 (14)	N1—C8—C9	122.9 (5)
O1i—Mn—O4i	89.62 (14)	N1—C8—H8	118.5
O1—Mn—O4i	90.38 (14)	C9—C8—H8	118.5
O4—Mn—O4i	180.00 (16)	C10—C9—C8	118.8 (5)
O1i—Mn—N1i	87.77 (14)	C10—C9—H9	120.6
O1—Mn—N1i	92.23 (14)	C8—C9—H9	120.6
O4—Mn—N1i	92.72 (14)	C9—C10—C11	119.2 (4)
O4i—Mn—N1i	87.28 (14)	C9—C10—H10	120.4
O1i—Mn—N1	92.23 (14)	C11—C10—H10	120.4
O1—Mn—N1	87.77 (14)	C12—C11—C10	118.2 (5)
O4—Mn—N1	87.28 (14)	C12—C11—C13	117.2 (4)
O4i—Mn—N1	92.72 (14)	C10—C11—C13	123.8 (4)
N1i—Mn—N1	180.0	N1—C12—C11	123.0 (5)
C1—O1—Mn	127.5 (3)	N1—C12—H12	118.5
Mn—O4—H41	100 (4)	C11—C12—H12	118.5
Mn—O4—H42	121 (5)	O3—C13—N2	120.8 (5)
H41—O4—H42	107 (4)	O3—C13—C11	119.4 (5)
C8—N1—C12	117.7 (4)	N2—C13—C11	119.7 (5)
C8—N1—Mn	123.5 (3)	C15—C14—N2	111.7 (7)
C12—N1—Mn	118.8 (3)	C15—C14—H14A	109.3
C13—N2—C14	124.8 (6)	N2—C14—H14A	109.3
C13—N2—C16	117.3 (6)	C15—C14—H14B	109.3
C14—N2—C16	117.8 (6)	N2—C14—H14B	109.3
O2—C1—O1	125.2 (5)	H14A—C14—H14B	107.9
O2—C1—C2	117.6 (5)	C14—C15—H15A	109.5
O1—C1—C2	117.1 (4)	C14—C15—H15B	109.5
C3—C2—C7	118.6 (5)	H15A—C15—H15B	109.5
C3—C2—C1	120.8 (5)	C14—C15—H15C	109.5
C7—C2—C1	120.6 (5)	H15A—C15—H15C	109.5
C2—C3—C4	121.2 (5)	H15B—C15—H15C	109.5
C2—C3—H3	119.4	C17—C16—N2	111.5 (7)
C4—C3—H3	119.4	C17—C16—H16A	109.3
C5—C4—C3	118.2 (5)	N2—C16—H16A	109.3
C5—C4—H4	120.9	C17—C16—H16B	109.3
C3—C4—H4	120.9	N2—C16—H16B	109.3
C6—C5—C4	122.2 (5)	H16A—C16—H16B	108.0
C6—C5—Cl	119.3 (5)	C16—C17—H17A	109.5
C4—C5—Cl	118.5 (5)	C16—C17—H17B	109.5
C5—C6—C7	119.1 (5)	H17A—C17—H17B	109.5
C5—C6—H6	120.5	C16—C17—H17C	109.5
C7—C6—H6	120.5	H17A—C17—H17C	109.5
C6—C7—C2	120.6 (5)	H17B—C17—H17C	109.5
O4—Mn—O1—C1	−164.0 (4)	C7—C2—C1—O2	2.8 (7)
O4i—Mn—O1—C1	16.0 (4)	C3—C2—C1—O1	3.3 (6)
N1i—Mn—O1—C1	103.3 (4)	C7—C2—C1—O1	−175.9 (4)
N1—Mn—O1—C1	−76.7 (4)	C7—C2—C3—C4	−1.7 (7)
O1i—Mn—N1—C8	−32.0 (4)	C1—C2—C3—C4	179.1 (5)
O1—Mn—N1—C8	148.0 (4)	C5—C4—C3—C2	0.5 (8)
O4—Mn—N1—C8	−122.3 (4)	C3—C4—C5—C6	0.4 (9)
O4i—Mn—N1—C8	57.7 (4)	C3—C4—C5—Cl	179.2 (4)
O1i—Mn—N1—C12	146.8 (4)	C4—C5—C6—C7	−0.1 (10)
O1—Mn—N1—C12	−33.2 (4)	Cl—C5—C6—C7	−178.9 (5)
O4—Mn—N1—C12	56.6 (4)	C2—C7—C6—C5	−1.2 (9)
O4i—Mn—N1—C12	−123.4 (4)	C10—C9—C8—N1	−0.6 (9)
Mn—O1—C1—O2	−31.6 (7)	C11—C10—C9—C8	−0.2 (8)
Mn—O1—C1—C2	146.9 (3)	C12—C11—C10—C9	−0.7 (8)
Mn—N1—C8—C9	−178.9 (4)	C13—C11—C10—C9	−170.7 (5)
C12—N1—C8—C9	2.2 (8)	C10—C11—C12—N1	2.4 (8)
C8—N1—C12—C11	−3.2 (8)	C13—C11—C12—N1	173.1 (5)
Mn—N1—C12—C11	177.9 (4)	O3—C13—N2—C14	−179.1 (6)
C13—N2—C14—C15	−111.0 (9)	C11—C13—N2—C14	−3.4 (10)
C16—N2—C14—C15	72.0 (10)	O3—C13—N2—C16	−2.2 (9)
C13—N2—C16—C17	81.2 (9)	C11—C13—N2—C16	173.5 (5)
C14—N2—C16—C17	−101.6 (9)	O3—C13—C11—C10	114.1 (6)
C3—C2—C7—C6	2.0 (8)	N2—C13—C11—C10	−61.6 (8)
C1—C2—C7—C6	−178.8 (5)	O3—C13—C11—C12	−55.9 (7)
C3—C2—C1—O2	−178.0 (4)	N2—C13—C11—C12	128.3 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H41···O2i	0.99 (4)	1.71 (5)	2.670 (6)	162 (7)
O4—H42···O3ii	0.93 (5)	1.85 (5)	2.766 (6)	168 (7)

Mn—O1	2.141 (3)
Mn—O4	2.205 (4)
Mn—N1	2.281 (4)

O1i—Mn—O4	90.38 (14)
O1—Mn—O4	89.62 (14)
O1—Mn—N1i	92.23 (14)
O4—Mn—N1i	92.72 (14)
O1—Mn—N1	87.77 (14)
O4—Mn—N1	87.28 (14)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H41⋯O2i	0.99 (4)	1.71 (5)	2.670 (6)	162 (7)
O4—H42⋯O3ii	0.93 (5)	1.85 (5)	2.766 (6)	168 (7)

Symmetry codes: (i) ; (ii) .