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

The title compound, [Mn(C(8)H(5)O(3))(2)(C(10)H(14)N(2)O)(2)(H(2)O)(2)], contains one Mn(II) atom lying on an inversion centre, two 4-formyl-benzoate and two diethyl-nicotinamide ligands and two coordinated water mol-ecules. All ligands are monodentate. The four O atoms around the Mn atom form a slightly distorted equatorial plane, while the distorted octa-hedral coordination is completed by the two N atoms in the axial positions. An intra-molecular O-H⋯O hydrogen bond occurs in the complex. In the crystal structure, O-H⋯O hydrogen bonds link the mol-ecules through an R(2) (2)(16) ring motif, forming a one-dimensional chain along the a axis. The π-π contact between the pyridyl rings [centroid-centroid distance = 3.629 (2) Å] may further stabilize the structure.

Related literature

For general background, see: Antolini et al. (1982 ▶); Nadzhafov et al. (1981 ▶); Shnulin et al. (1981 ▶). For related structures, see: Hökelek et al. (1995 ▶, 1997 ▶, 2007 ▶, 2008 ▶); Hökelek & Necefoğlu (1996 ▶, 1997 ▶, 2007 ▶). For hydrogen-bonding motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

[Mn(C8H5O3)2(C10H14N2O)2(H2O)2]

M = 745.68

Triclinic,

a = 7.3266 (2) Å

b = 8.6618 (2) Å

c = 16.0687 (3) Å

α = 86.381 (8)°

β = 78.272 (7)°

γ = 68.618 (6)°

V = 929.67 (6) Å3

Z = 1

Mo Kα radiation

μ = 0.42 mm−1

T = 294 K

0.35 × 0.20 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.904, T max = 0.935

18356 measured reflections

3799 independent reflections

3317 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.157

S = 1.02

3799 reflections

246 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.77 e Å−3

Δρmin = −0.32 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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/S1600536809006047/hy2182sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006047/hy2182Isup2.hkl

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

[Mn(C8H5O3)2(C10H14N2O)2(H2O)2]	Z = 1
Mr = 745.68	F(000) = 391
Triclinic, P1	Dx = 1.332 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3266 (2) Å	Cell parameters from 2942 reflections
b = 8.6618 (2) Å	θ = 2.5–26.4°
c = 16.0687 (3) Å	µ = 0.42 mm−1
α = 86.381 (8)°	T = 294 K
β = 78.272 (7)°	Block, colourless
γ = 68.618 (6)°	0.35 × 0.20 × 0.15 mm
V = 929.67 (6) Å3

Rigaku R-AXIS RAPID-S diffractometer	3799 independent reflections
Radiation source: fine-focus sealed tube	3317 reflections with I > 2σ(I)
graphite	Rint = 0.071
ω scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
Tmin = 0.904, Tmax = 0.935	k = −10→10
18356 measured reflections	l = −20→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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0681P)2 + 0.7177P] where P = (Fo2 + 2Fc2)/3
3799 reflections	(Δ/σ)max < 0.001
246 parameters	Δρmax = 0.77 e Å−3
3 restraints	Δρmin = −0.32 e Å−3

	x	y	z	Uiso*/Ueq
Mn1	0.5000	0.5000	0.5000	0.04035 (19)
O1	0.5226 (3)	0.6203 (2)	0.60914 (12)	0.0488 (5)
O2	0.2455 (3)	0.6315 (3)	0.70146 (14)	0.0583 (5)
O3	0.9452 (5)	0.6893 (5)	0.95632 (19)	0.1013 (11)
O4	−0.2292 (3)	0.8295 (3)	0.37375 (14)	0.0615 (6)
O5	0.2143 (3)	0.4822 (3)	0.56750 (14)	0.0548 (5)
H51	0.209 (7)	0.378 (3)	0.579 (3)	0.089 (13)*
H52	0.202 (7)	0.529 (5)	0.6197 (17)	0.095 (14)*
N1	0.3151 (3)	0.7460 (3)	0.44777 (14)	0.0440 (5)
N2	−0.1135 (5)	0.9208 (4)	0.24863 (17)	0.0644 (7)
C1	0.4205 (4)	0.6295 (3)	0.68336 (17)	0.0439 (6)
C2	0.5205 (4)	0.6365 (3)	0.75573 (17)	0.0428 (6)
C3	0.7119 (4)	0.6417 (4)	0.74021 (17)	0.0473 (6)
H3	0.7806	0.6384	0.6845	0.057*
C4	0.8014 (5)	0.6518 (4)	0.80646 (19)	0.0532 (7)
H4	0.9292	0.6560	0.7954	0.064*
C5	0.6993 (5)	0.6556 (4)	0.88983 (19)	0.0551 (7)
C6	0.5098 (5)	0.6475 (4)	0.90521 (19)	0.0579 (8)
H6	0.4424	0.6482	0.9609	0.069*
C7	0.4202 (4)	0.6384 (4)	0.83915 (18)	0.0519 (7)
H7	0.2927	0.6336	0.8503	0.062*
C8	0.7904 (7)	0.6678 (6)	0.9615 (2)	0.0760 (11)
H8	0.712 (5)	0.658 (4)	1.0166 (14)	0.062 (10)*
C9	0.3345 (4)	0.8906 (3)	0.45861 (18)	0.0470 (6)
H9	0.4275	0.8922	0.4899	0.056*
C10	0.2234 (5)	1.0371 (4)	0.4256 (2)	0.0525 (7)
H10	0.2408	1.1354	0.4348	0.063*
C11	0.0859 (4)	1.0359 (3)	0.37870 (19)	0.0498 (7)
H11	0.0102	1.1330	0.3550	0.060*
C12	0.0623 (4)	0.8875 (3)	0.36748 (17)	0.0430 (6)
C13	0.1776 (4)	0.7474 (3)	0.40382 (17)	0.0446 (6)
H13	0.1590	0.6484	0.3976	0.054*
C14	−0.1018 (4)	0.8756 (4)	0.32858 (19)	0.0495 (7)
C15	0.0357 (6)	0.9707 (5)	0.1895 (2)	0.0743 (10)
H15A	−0.0323	1.0752	0.1641	0.089*
H15B	0.1251	0.9892	0.2214	0.089*
C16	0.1546 (9)	0.8495 (9)	0.1215 (4)	0.141 (3)
H16A	0.2588	0.8837	0.0896	0.212*
H16B	0.0702	0.8423	0.0845	0.212*
H16C	0.2126	0.7429	0.1459	0.212*
C17	−0.2907 (7)	0.9202 (5)	0.2173 (3)	0.0779 (11)
H17A	−0.4094	0.9678	0.2607	0.093*
H17B	−0.3065	0.9890	0.1673	0.093*
C18	−0.2717 (9)	0.7511 (6)	0.1959 (3)	0.1023 (16)
H18A	−0.3799	0.7568	0.1692	0.153*
H18B	−0.2757	0.6873	0.2468	0.153*
H18C	−0.1470	0.6992	0.1576	0.153*

	U11	U22	U33	U12	U13	U23
Mn1	0.0401 (3)	0.0417 (3)	0.0406 (3)	−0.0139 (2)	−0.0145 (2)	0.0073 (2)
O1	0.0549 (12)	0.0520 (11)	0.0436 (10)	−0.0219 (9)	−0.0147 (9)	0.0043 (8)
O2	0.0448 (12)	0.0728 (15)	0.0577 (12)	−0.0197 (10)	−0.0128 (9)	−0.0024 (10)
O3	0.101 (2)	0.160 (3)	0.0737 (18)	−0.074 (2)	−0.0370 (16)	0.0082 (18)
O4	0.0537 (13)	0.0754 (15)	0.0651 (13)	−0.0343 (11)	−0.0159 (10)	0.0127 (11)
O5	0.0515 (12)	0.0615 (14)	0.0575 (13)	−0.0275 (10)	−0.0119 (10)	0.0061 (10)
N1	0.0426 (12)	0.0416 (12)	0.0481 (12)	−0.0131 (10)	−0.0153 (10)	0.0056 (9)
N2	0.0708 (18)	0.0782 (19)	0.0571 (15)	−0.0356 (15)	−0.0286 (13)	0.0165 (13)
C1	0.0459 (15)	0.0347 (13)	0.0483 (15)	−0.0089 (11)	−0.0142 (12)	0.0024 (10)
C2	0.0464 (14)	0.0369 (13)	0.0441 (14)	−0.0123 (11)	−0.0119 (11)	0.0024 (10)
C3	0.0479 (15)	0.0526 (16)	0.0414 (14)	−0.0197 (13)	−0.0060 (11)	0.0019 (11)
C4	0.0507 (16)	0.0617 (18)	0.0523 (16)	−0.0245 (14)	−0.0142 (13)	0.0034 (13)
C5	0.0603 (18)	0.0636 (19)	0.0451 (15)	−0.0244 (15)	−0.0147 (13)	0.0027 (13)
C6	0.0629 (19)	0.070 (2)	0.0395 (14)	−0.0251 (16)	−0.0068 (13)	0.0039 (13)
C7	0.0466 (16)	0.0579 (17)	0.0485 (15)	−0.0167 (13)	−0.0080 (12)	0.0025 (13)
C8	0.083 (3)	0.106 (3)	0.0521 (19)	−0.046 (2)	−0.0225 (18)	0.0047 (19)
C9	0.0475 (15)	0.0481 (15)	0.0506 (15)	−0.0200 (12)	−0.0165 (12)	0.0040 (12)
C10	0.0562 (17)	0.0428 (15)	0.0634 (18)	−0.0216 (13)	−0.0175 (14)	0.0072 (13)
C11	0.0514 (16)	0.0393 (14)	0.0582 (17)	−0.0141 (12)	−0.0174 (13)	0.0122 (12)
C12	0.0379 (13)	0.0458 (15)	0.0438 (14)	−0.0133 (11)	−0.0099 (10)	0.0061 (11)
C13	0.0452 (14)	0.0398 (14)	0.0511 (15)	−0.0149 (11)	−0.0163 (12)	0.0048 (11)
C14	0.0471 (15)	0.0512 (16)	0.0522 (16)	−0.0172 (13)	−0.0178 (12)	0.0099 (12)
C15	0.087 (3)	0.083 (3)	0.058 (2)	−0.035 (2)	−0.0189 (18)	0.0101 (18)
C16	0.115 (5)	0.184 (7)	0.129 (5)	−0.072 (5)	0.023 (4)	−0.060 (5)
C17	0.090 (3)	0.075 (2)	0.082 (3)	−0.033 (2)	−0.046 (2)	0.0196 (19)
C18	0.138 (4)	0.085 (3)	0.097 (3)	−0.039 (3)	−0.054 (3)	0.004 (2)

Mn1—O1i	2.1596 (18)	C6—H6	0.9300
Mn1—O1	2.1596 (18)	C7—C6	1.377 (4)
Mn1—O5	2.207 (2)	C7—H7	0.9300
Mn1—O5i	2.207 (2)	C8—H8	0.971 (18)
Mn1—N1	2.283 (2)	C9—C10	1.375 (4)
Mn1—N1i	2.283 (2)	C9—H9	0.9300
O1—C1	1.262 (3)	C10—H10	0.9300
O2—C1	1.249 (3)	C11—C10	1.379 (4)
O3—C8	1.201 (5)	C11—H11	0.9300
O4—C14	1.232 (4)	C12—C11	1.385 (4)
O5—H51	0.924 (19)	C12—C13	1.375 (4)
O5—H52	0.926 (19)	C12—C14	1.500 (4)
N1—C9	1.337 (3)	C13—H13	0.9300
N1—C13	1.339 (3)	C15—C16	1.465 (7)
N2—C14	1.330 (4)	C15—H15A	0.9700
N2—C15	1.468 (5)	C15—H15B	0.9700
N2—C17	1.487 (4)	C16—H16A	0.9600
C2—C1	1.510 (4)	C16—H16B	0.9600
C2—C3	1.391 (4)	C16—H16C	0.9600
C2—C7	1.389 (4)	C17—C18	1.477 (6)
C3—C4	1.381 (4)	C17—H17A	0.9700
C3—H3	0.9300	C17—H17B	0.9700
C4—H4	0.9300	C18—H18A	0.9600
C5—C4	1.391 (4)	C18—H18B	0.9600
C5—C6	1.386 (5)	C18—H18C	0.9600
C5—C8	1.470 (4)
O1i—Mn1—O1	180.000 (1)	O3—C8—C5	126.0 (4)
O1i—Mn1—O5	89.23 (8)	O3—C8—H8	121 (2)
O1—Mn1—O5	90.77 (8)	C5—C8—H8	113 (2)
O1i—Mn1—O5i	90.77 (8)	N1—C9—C10	123.1 (3)
O1—Mn1—O5i	89.23 (8)	N1—C9—H9	118.4
O1i—Mn1—N1i	92.23 (8)	C10—C9—H9	118.4
O1—Mn1—N1	92.23 (8)	C9—C10—C11	118.9 (3)
O1—Mn1—N1i	87.77 (8)	C9—C10—H10	120.6
O1i—Mn1—N1	87.77 (8)	C11—C10—H10	120.6
O5—Mn1—O5i	180.000 (1)	C10—C11—C12	118.8 (3)
O5—Mn1—N1i	92.95 (8)	C10—C11—H11	120.6
O5i—Mn1—N1i	87.05 (8)	C12—C11—H11	120.6
O5—Mn1—N1	87.05 (8)	C11—C12—C14	123.3 (2)
O5i—Mn1—N1	92.95 (8)	C13—C12—C11	118.3 (3)
N1i—Mn1—N1	180.00 (10)	C13—C12—C14	117.8 (2)
Mn1—O5—H52	101 (3)	N1—C13—C12	123.5 (3)
Mn1—O5—H51	118 (3)	N1—C13—H13	118.3
H52—O5—H51	106 (4)	C12—C13—H13	118.3
C1—O1—Mn1	126.76 (18)	O4—C14—N2	121.2 (3)
C9—N1—C13	117.3 (2)	O4—C14—C12	118.1 (3)
C9—N1—Mn1	124.02 (18)	N2—C14—C12	120.6 (3)
C13—N1—Mn1	118.65 (17)	N2—C15—H15A	108.7
C14—N2—C15	124.7 (3)	N2—C15—H15B	108.7
C14—N2—C17	117.3 (3)	C16—C15—N2	114.1 (4)
C15—N2—C17	118.0 (3)	C16—C15—H15A	108.7
O1—C1—C2	116.8 (2)	C16—C15—H15B	108.7
O2—C1—C2	117.8 (2)	H15A—C15—H15B	107.6
O2—C1—O1	125.4 (3)	C15—C16—H16A	109.5
C3—C2—C1	120.9 (2)	C15—C16—H16B	109.5
C7—C2—C1	119.8 (3)	C15—C16—H16C	109.5
C7—C2—C3	119.3 (3)	H16A—C16—H16B	109.5
C2—C3—H3	119.6	H16A—C16—H16C	109.5
C4—C3—C2	120.9 (3)	H16B—C16—H16C	109.5
C4—C3—H3	119.6	N2—C17—H17A	109.2
C3—C4—C5	119.6 (3)	N2—C17—H17B	109.2
C3—C4—H4	120.2	C18—C17—N2	111.8 (4)
C5—C4—H4	120.2	C18—C17—H17A	109.2
C4—C5—C8	120.7 (3)	C18—C17—H17B	109.2
C6—C5—C4	119.5 (3)	H17A—C17—H17B	107.9
C6—C5—C8	119.9 (3)	C17—C18—H18A	109.5
C5—C6—H6	119.5	C17—C18—H18B	109.5
C7—C6—C5	120.9 (3)	C17—C18—H18C	109.5
C7—C6—H6	119.5	H18A—C18—H18B	109.5
C2—C7—H7	120.1	H18A—C18—H18C	109.5
C6—C7—C2	119.9 (3)	H18B—C18—H18C	109.5
C6—C7—H7	120.1
O5—Mn1—O1—C1	13.3 (2)	C3—C2—C1—O1	3.4 (4)
O5i—Mn1—O1—C1	−166.7 (2)	C7—C2—C1—O1	−176.9 (2)
N1i—Mn1—O1—C1	−79.6 (2)	C3—C2—C1—O2	−177.3 (3)
N1—Mn1—O1—C1	100.4 (2)	C7—C2—C1—O2	2.5 (4)
O1i—Mn1—N1—C9	−148.3 (2)	C1—C2—C3—C4	178.6 (3)
O1—Mn1—N1—C9	31.7 (2)	C7—C2—C3—C4	−1.2 (4)
O1i—Mn1—N1—C13	32.1 (2)	C1—C2—C7—C6	−178.9 (3)
O1—Mn1—N1—C13	−147.9 (2)	C3—C2—C7—C6	0.8 (4)
O5—Mn1—N1—C9	122.4 (2)	C2—C3—C4—C5	0.4 (5)
O5i—Mn1—N1—C9	−57.6 (2)	C6—C5—C4—C3	0.7 (5)
O5—Mn1—N1—C13	−57.2 (2)	C8—C5—C4—C3	−179.5 (3)
O5i—Mn1—N1—C13	122.8 (2)	C4—C5—C6—C7	−1.1 (5)
Mn1—O1—C1—O2	−29.8 (4)	C8—C5—C6—C7	179.1 (4)
Mn1—O1—C1—C2	149.49 (18)	C4—C5—C8—O3	6.7 (7)
Mn1—N1—C9—C10	179.1 (2)	C6—C5—C8—O3	−173.4 (4)
C13—N1—C9—C10	−1.2 (4)	C2—C7—C6—C5	0.3 (5)
Mn1—N1—C13—C12	−178.0 (2)	N1—C9—C10—C11	−0.3 (5)
C9—N1—C13—C12	2.3 (4)	C12—C11—C10—C9	0.9 (5)
C15—N2—C14—O4	−177.4 (3)	C13—C12—C11—C10	0.0 (4)
C17—N2—C14—O4	2.5 (5)	C14—C12—C11—C10	171.0 (3)
C15—N2—C14—C12	5.6 (5)	C11—C12—C13—N1	−1.7 (4)
C17—N2—C14—C12	−174.4 (3)	C14—C12—C13—N1	−173.2 (3)
C14—N2—C15—C16	108.8 (5)	C11—C12—C14—O4	−114.4 (3)
C17—N2—C15—C16	−71.1 (5)	C11—C12—C14—N2	62.7 (4)
C14—N2—C17—C18	−78.2 (5)	C13—C12—C14—O4	56.7 (4)
C15—N2—C17—C18	101.7 (4)	C13—C12—C14—N2	−126.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O4ii	0.92 (3)	1.87 (3)	2.775 (3)	165 (4)
O5—H52···O2	0.93 (3)	1.77 (4)	2.669 (3)	162 (4)

Table 1

Selected bond lengths (Å)

Mn1—O1	2.1596 (18)
Mn1—O5	2.207 (2)
Mn1—N1	2.283 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H51⋯O4i	0.92 (3)	1.87 (3)	2.775 (3)	165 (4)
O5—H52⋯O2	0.93 (3)	1.77 (4)	2.669 (3)	162 (4)

Symmetry code: (i) .