Diaqua­bis(N,N-diethyl­nicotinamide-κN1)bis­(4-formyl­benzoato-κO1)manganese(II)

Sertçelik, M.; Tercan, B.; Şahin, E.; Necefoğlu, H.; Hökelek, T.

doi:10.1107/S1600536809006047

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Pages m324-m325

doi:10.1107/S1600536809006047

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Diaquabis(N,N-diethylnicotinamide-κN¹)bis(4-formylbenzoato-κO¹)manganese(II)

Mustafa Sertçelik,^a Barış Tercan,^b Ertan Şahin,^c Hacali Necefoğlu ^a and Tuncer Hökelek ^d ^*

^aDepartment of Chemistry, Kafkas University, 63100 Kars, Turkey, ^bDepartment of Physics, Karabük University, 78050 Karabük, Turkey, ^cDepartment of Chemistry, Atatürk University, 22240 Erzurum, Turkey, and ^dDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 26 January 2009; accepted 19 February 2009; online 25 February 2009)

The title compound, [Mn(C₈H₅O₃)₂(C₁₀H₁₄N₂O)₂(H₂O)₂], contains one Mn^II atom lying on an inversion centre, two 4-formylbenzoate and two diethylnicotinamide ligands and two coordinated water molecules. All ligands are monodentate. The four O atoms around the Mn atom form a slightly distorted equatorial plane, while the distorted octahedral coordination is completed by the two N atoms in the axial positions. An intramolecular O—H⋯O hydrogen bond occurs in the complex. In the crystal structure, O—H⋯O hydrogen bonds link the molecules through an R₂²(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_r = 745.68
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.058
wR(F²) = 0.157
S = 1.02
3799 reflections
246 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.77 e Å⁻³
Δρ_min = −0.32 e Å⁻³

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) -x, -y+1, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006047/hy2182sup1.cif

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

checkCIF report

Comment top

The structural functions and coordination relationships of the arylcarboxylates in transition metal complexes of benzoic acid derivatives change depending on the nature and position of the substituent groups on the benzene ring, the nature of the additional ligand molecules or solvents, and the medium of the synthesis (Nadzhafov et al., 1981; Shnulin et al., 1981). Transition metal complexes with biochemically active ligands frequently show interesting physical and/or chemical properties, and as a result, they may find applications in biological systems (Antolini et al., 1982). The structure determination of the title compound, (I), a manganese complex with two formylbenzoate (FOB) and two diethylnicotinamide (DENA) ligands and two water molecules, was undertaken in order to determine the properties of the ligands and also to compare the results obtained with those reported previously.

Compound (I) is a monomeric complex, with the Mn^II atom lying on a centre of symmetry. It contains two FOB and two DENA ligands and two water molecules (Fig. 1). All ligands are monodentate. The four O atoms [O1, O5, and the symmetry-related atoms, O1ⁱⁱ, O5ⁱⁱ; symmetry code: (ii) 1 - x, 1 - y, 1 - z] around the Mn atom form a slightly distorted equatorial plane, while the slightly distorted octahedral coordination is completed by the two N atoms of the DENA ligands (N1, N1ⁱⁱ) in the axial positions (Table 1 and Fig. 1). The intramolecular O—H···O hydrogen bond (Table 2) results in the formation of a six-membered ring (Mn1, O1, O2, O5, C1, H52), which adopts envelope conformation with C1 atom displaced by -0.235 (3) Å from the plane of the other five atoms.

The near equality of the C1—O1 [1.262 (3) Å] and C1—O2 [1.249 (3) Å] bonds in the carboxylate group indicates a delocalized bonding arrangement, rather than localized single and double bonds, and may be compared with the corresponding distances: 1.256 (6) and 1.245 (6) Å in [Mn(DENA)₂(C₇H₄ClO₂)₂(H₂O)₂], (II), (Hökelek et al., 2008), 1.265 (6) and 1.275 (6) Å in [Mn(C₉H₁₀NO₂)₂(H₂O)₄].2H₂O, (III), (Hökelek & Necefoğlu, 2007), 1.260 (4) and 1.252 (4) Å in [Zn(DENA)₂(C₇H₄FO₂)₂(H₂O)₂], (IV), (Hökelek et al., 2007), 1.259 (9) and 1.273 (9) Å in [Cu₂(DENA)₂(C₆H₅COO)₄], (V), (Hökelek et al., 1995), 1.279 (4) and 1.246 (4) Å in [Zn₂(DENA)₂(C₇H₅O₃)₄].2H₂O, (VI), (Hökelek & Necefoğlu, 1996), 1.251 (6) and 1.254 (7) Å in [Co(DENA)₂(C₇H₅O₃)₂(H₂O)₂], (VII), (Hökelek & Necefoğlu, 1997), 1.278 (3) and 1.246 (3) Å in [Cu(DENA)₂(C₇H₄NO₄)₂(H₂O)₂], (VIII), (Hökelek et al., 1997). This may be due to the intramolecular O—H···O hydrogen bond involving the carboxylate O atom (Table 2). In (I), the average Mn—O bond length is 2.183 (2) Å and the Mn atom is displaced out of the least-squares plane of the carboxylate group (O1, C1, O2) by -0.859 (1) Å. They are reported as -0.890 (1) Å in (II) and 2.185 (4) and 1.365 (3) Å in (III). The dihedral angle between the planar carboxylate group and the benzene ring A (C2–C7) is 3.0 (2)°, while that between rings A and B (N1, C9–C13) is 80.0 (1)°.

In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 2) link the molecules through a R²₂(16) ring motif (Bernstein et al., 1995) to form a one-dimensional chain along the a axis (Fig. 2). The π-π contact between the pyridyl rings of DENA ligands, Cg1···Cg1ⁱⁱⁱ [symmetry code: (iii) -x, 2 - y, 1 - z; where Cg1 is the centroid of ring B] may further stabilize the structure, with centroid–centroid distance of 3.629 (2) Å.

Related literature top

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 top

The title compound was prepared by the reaction of Mn(SO₄).H₂O (1.69 g, 10 mmol) in H₂O (50 ml) and DENA (3.56 g, 20 mmol) in H₂O (15 ml) with sodium 4-formylbenzoate (3.44 g, 20 mmol) in H₂O (50 ml). The mixture was filtered and set aside to crystallize at ambient temperature for several days, giving colourless single crystals.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); 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).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 40% probability level. Hydrogen bonds are shown as dashed lines. [Symmetry code: (ii) 1 - x, 1 - y, 1 - z.]
	Fig. 2. A partial packing diagram of the title compound, showing hydrogen bonds (dashed lines) linking the molecules through the R²₂(16) ring motif. H atoms not involved in hydrogen bonds are omitted for clarity.

Diaquabis(N,N-diethylnicotinamide-κN¹)bis(4- formylbenzoato-κO¹)manganese(II) top

Crystal data top

[Mn(C₈H₅O₃)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]	Z = 1
M_r = 745.68	F(000) = 391
Triclinic, P1	D_x = 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

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	3799 independent reflections
Radiation source: fine-focus sealed tube	3317 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
ω scans	θ_max = 26.4°, θ_min = 2.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
T_min = 0.904, T_max = 0.935	k = −10→10
18356 measured reflections	l = −20→20

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)] = 0.058	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(F_o²) + (0.0681P)² + 0.7177P] where P = (F_o² + 2F_c²)/3
3799 reflections	(Δ/σ)_max < 0.001
246 parameters	Δρ_max = 0.77 e Å⁻³
3 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Mn(C₈H₅O₃)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]	γ = 68.618 (6)°
M_r = 745.68	V = 929.67 (6) Å³
Triclinic, P1	Z = 1
a = 7.3266 (2) Å	Mo Kα radiation
b = 8.6618 (2) Å	µ = 0.42 mm⁻¹
c = 16.0687 (3) Å	T = 294 K
α = 86.381 (8)°	0.35 × 0.20 × 0.15 mm
β = 78.272 (7)°

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	3799 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3317 reflections with I > 2σ(I)
T_min = 0.904, T_max = 0.935	R_int = 0.071
18356 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	3 restraints
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.77 e Å⁻³
3799 reflections	Δρ_min = −0.32 e Å⁻³
246 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

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)

Symmetry code: (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Mn(C₈H₅O₃)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]
M_r	745.68
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	7.3266 (2), 8.6618 (2), 16.0687 (3)
α, β, γ (°)	86.381 (8), 78.272 (7), 68.618 (6)
V (Å³)	929.67 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.35 × 0.20 × 0.15

Data collection
Diffractometer	Rigaku R-AXIS RAPID-S diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.904, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	18356, 3799, 3317
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.157, 1.02
No. of reflections	3799
No. of parameters	246
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.77, −0.32

Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z+1.

Acknowledgements

The authors are indebted to the Department of Chemistry, Atatürk University, Erzurum, Turkey, for the use of X-ray diffractometer purchased under grant No. 2003/219 of the University Research Fund.

References

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