Diaqua­(2,6-dioxo-1,2,3,6-tetra­hydro­pyrimidin-3-ide-4-carboxyl­ato-κ2N3,O4)(1,10-phenanthroline-κ2N,N′)manganese(II)

Wu, R.; Huo, Y.; Li, J.; Zheng, Z.

doi:10.1107/S1600536808005230

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Pages m500-m501

doi:10.1107/S1600536808005230

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Diaqua(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-3-ide-4-carboxylato-κ²N³,O⁴)(1,10-phenanthroline-κ²N,N′)manganese(II)

Rentao Wu,^a ^* Yanmin Huo,^b Jikun Li ^c and Zebao Zheng ^a

^aDepartment of Chemistry, Taishan University, 271021 Tai'an, Shandong, People's Republic of China, ^bShan Dong Institute of Supervision & Inspection of Product Quality, 250100 Ji'nan, Shandong, People's Republic of China, and ^cDepartment of Materials and Chemical Engineering, Taishan University, 271021 Tai'an, Shandong, People's Republic of China
^*Correspondence e-mail: duanwenzeng@163.com

(Received 27 December 2007; accepted 25 February 2008; online 29 February 2008)

The title compound, [Mn(C₅H₂N₂O₄)(C₁₂H₈N₂)(H₂O)₂], was synthesized by the reaction of manganese(II) acetate and orotic acid in the presence of 1,10-phenanthroline. The crystal structure exhibits intermolecular N—H⋯O and O—H⋯O hydrogen bonds . The Mn coordination environment consists of an N₃O₃ donor set in an octahedral geometry.

Related literature

For biochemical processes, see: Mukhopadhyay et al., (2004 ); Ren et al., (2005 ). For bioinorganic and pharmaceutical studies, see: Lieberman et al., (1955 ). For coordination chemistry and other aspects, see: Darensbourg et al., (1998 ). For complexes of the orotate ligand, see: Hambley et al., (1995 ); Nepveu et al., (1995 ).

Experimental

Crystal data

[Mn(C₅H₂N₂O₄)(C₁₂H₈N₂)(H₂O)₂]
M_r = 425.26
Triclinic, $[P \overline 1]$
a = 8.3173 (2) Å
b = 8.9875 (2) Å
c = 11.9509 (3) Å
α = 78.2780 (10)°
β = 82.9100 (10)°
γ = 74.7440 (10)°
V = 841.58 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.83 mm⁻¹
T = 293 (2) K
0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.885, T_max = 0.921
9718 measured reflections
2950 independent reflections
2539 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.072
S = 1.05
2950 reflections
257 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Selected bond lengths (Å)

Mn1—O1	2.1231 (15)
Mn1—O6	2.1439 (15)
Mn1—O5	2.1852 (16)
Mn1—N1	2.2686 (16)
Mn1—N3	2.2880 (18)
Mn1—N4	2.2979 (19)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4ⁱ	0.86	1.97	2.831 (2)	177
O5—H5A⋯O4ⁱⁱ	0.85	2.00	2.829 (2)	164
O5—H5B⋯O3ⁱⁱⁱ	0.85	1.95	2.769 (2)	162
O6—H6A⋯O2^iv	0.85	1.79	2.627 (2)	170
O6—H6B⋯O3	0.85	1.92	2.675 (2)	147
Symmetry codes: (i) -x+1, -y-1, -z+2; (ii) -x+1, -y, -z+2; (iii) -x, -y, -z+2; (iv) x-1, y, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808005230/om2206sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808005230/om2206Isup2.hkl

checkCIF report

Comment top

Manganese is an important element in organisms and involved in many biochemical processes (Mukhopadhyay et al., 2004 and Ren et al., 2005). It may be observed in the active parts of many enzymes. Orotic acid (2, 6-dioxo-1, 2, 3, 6-tetrahydropyrimidine-4- carboxylic acid), an important pyrimidine derivative as the effective precursor in the biosynthesis of pyrimidine base of nucleic acids in living organisms, plays an important role in bioinorganic chemistry and pharmaceutical studies (Lieberman et al., 1955), material science, coordination chemistry and other aspects (Darensbourg et al., 1998). Many complexes of the orotate ligand have been reported (Hambley et al., 1995).

In the title compound (Fig, 1), Mn(C₁₂H₈N₂)(C₅H₂N₂O₄)(H₂O)₂, the Mn(II) ion is coordinated by N and O atoms from the orotate (2, 6-dioxo-1, 2, 3, 6-tetrahydropyrimidine- 4-carboxylate) ligand. The bond lengths and angles are in good agreement with reported values (Nepveu et al., 1995). In the crystal structure, the molecule with its two coordinated water molecules is linked into infinite chains by O—H···O and N—H···O hydrogen bonds.

Related literature top

For biochemical processes, see: Mukhopadhyay et al., (2004); Ren et al., (2005). For bioinorganic and pharmaceutical studies, see: Lieberman et al., (1955). For coordination chemistry and other aspects, see: Darensbourg et al., (1998). For complexes of the orotate ligand, see: Hambley et al., (1995); Nepveu et al., (1995).

Experimental top

Orotic acid (0.0012 mol), 1, 10-phenanthroline (0.0012 mol) and Mn(CH₃COO)₂.2H₂O (0.0012 mol, 0.294 g) in 120 ml of water were stirred at 373 K for 24 h; the pH of the solution was adjusted to 6 using a dilute aqueous solution of ammonia. After evaporation of the solution for two weeks, colorless block-like crystals were isolated by filtration. Analysis, calculated for C₁₇H₁₄N₄O₆Mn: C 48.01, H 3.32, N 13.17; found: C 48.00, H 3.30, N 13.16. Crystals suitable for single-crystal X-ray analysis were selected directly from the sample.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. The H atoms are omitted.

Diaqua(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-3-ide-4-carboxylato-\k²N³,O⁴)(1,10-phenanthroline-κ²N,N')manganese(II) top

Crystal data top

[Mn(C₅H₂N₂O₄)(C₁₂H₈N₂)(H₂O)₂]	Z = 2
M_r = 425.26	F(000) = 434
Triclinic, P1	D_x = 1.678 Mg m⁻³
a = 8.3173 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9875 (2) Å	Cell parameters from 3161 reflections
c = 11.9509 (3) Å	θ = 2.4–24.5°
α = 78.278 (1)°	µ = 0.83 mm⁻¹
β = 82.910 (1)°	T = 293 K
γ = 74.744 (1)°	Block, colorless
V = 841.58 (3) Å³	0.15 × 0.12 × 0.10 mm

Data collection top

Bruker SMART diffractometer	2950 independent reflections
Radiation source: fine-focus sealed tube	2539 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.886, T_max = 0.922	k = −10→10
9718 measured reflections	l = −14→13

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0269P)² + 0.4894P] where P = (F_o² + 2F_c²)/3
2950 reflections	(Δ/σ)_max = 0.001
257 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

[Mn(C₅H₂N₂O₄)(C₁₂H₈N₂)(H₂O)₂]	γ = 74.744 (1)°
M_r = 425.26	V = 841.58 (3) Å³
Triclinic, P1	Z = 2
a = 8.3173 (2) Å	Mo Kα radiation
b = 8.9875 (2) Å	µ = 0.83 mm⁻¹
c = 11.9509 (3) Å	T = 293 K
α = 78.278 (1)°	0.15 × 0.12 × 0.10 mm
β = 82.910 (1)°

Data collection top

Bruker SMART diffractometer	2950 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2539 reflections with I > 2σ(I)
T_min = 0.886, T_max = 0.922	R_int = 0.027
9718 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.072	H-atom parameters constrained
S = 1.05	Δρ_max = 0.22 e Å⁻³
2950 reflections	Δρ_min = −0.22 e Å⁻³
257 parameters

Special details top

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	0.11775 (4)	0.19441 (4)	0.78756 (3)	0.03047 (11)
N1	0.2989 (2)	−0.03517 (19)	0.85359 (15)	0.0276 (4)
N2	0.3993 (2)	−0.29802 (19)	0.93896 (15)	0.0305 (4)
H2	0.3786	−0.3884	0.9636	0.037*
N3	−0.0891 (2)	0.3718 (2)	0.68697 (16)	0.0336 (4)
N4	0.1453 (2)	0.1395 (2)	0.60556 (16)	0.0358 (4)
O1	0.35761 (18)	0.24240 (17)	0.75978 (15)	0.0416 (4)
O2	0.62451 (19)	0.16456 (19)	0.79231 (17)	0.0532 (5)
O3	0.13026 (17)	−0.20586 (16)	0.89654 (13)	0.0335 (4)
O4	0.66615 (18)	−0.40215 (16)	0.98859 (14)	0.0385 (4)
O5	0.0660 (2)	0.33271 (19)	0.92439 (14)	0.0414 (4)
H5A	0.1454	0.3672	0.9392	0.085 (11)*
H5B	0.0168	0.3024	0.9883	0.084 (11)*
O6	−0.07494 (19)	0.08117 (19)	0.86706 (15)	0.0437 (4)
H6A	−0.1673	0.1030	0.8365	0.071 (10)*
H6B	−0.0474	−0.0182	0.8853	0.081 (11)*
C1	0.4836 (3)	0.1428 (2)	0.79908 (19)	0.0312 (5)
C2	0.4575 (2)	−0.0191 (2)	0.85488 (17)	0.0258 (4)
C3	0.5858 (3)	−0.1354 (2)	0.89906 (19)	0.0304 (5)
H3	0.6906	−0.1167	0.8987	0.036*
C4	0.5589 (3)	−0.2856 (2)	0.94576 (18)	0.0294 (5)
C5	0.2696 (2)	−0.1773 (2)	0.89586 (17)	0.0266 (4)
C6	−0.2058 (3)	0.4826 (3)	0.7282 (2)	0.0450 (6)
H6	−0.2016	0.4959	0.8028	0.054*
C7	−0.3352 (3)	0.5805 (3)	0.6641 (3)	0.0534 (7)
H7	−0.4157	0.6565	0.6962	0.064*
C8	−0.3428 (3)	0.5639 (3)	0.5547 (3)	0.0506 (7)
H8	−0.4273	0.6299	0.5110	0.061*
C9	−0.2226 (3)	0.4470 (3)	0.5079 (2)	0.0409 (6)
C10	−0.2204 (3)	0.4214 (3)	0.3930 (2)	0.0508 (7)
H10	−0.3020	0.4849	0.3458	0.061*
C11	−0.1026 (4)	0.3072 (3)	0.3523 (2)	0.0518 (7)
H11	−0.1045	0.2926	0.2776	0.062*
C12	0.0259 (3)	0.2076 (3)	0.4220 (2)	0.0427 (6)
C13	0.1512 (4)	0.0871 (3)	0.3838 (2)	0.0521 (7)
H13	0.1534	0.0681	0.3099	0.062*
C14	0.2700 (3)	−0.0023 (3)	0.4549 (2)	0.0525 (7)
H14	0.3547	−0.0817	0.4300	0.063*
C15	0.2621 (3)	0.0277 (3)	0.5655 (2)	0.0439 (6)
H15	0.3431	−0.0342	0.6138	0.053*
C16	0.0279 (3)	0.2301 (3)	0.53475 (19)	0.0343 (5)
C17	−0.0985 (3)	0.3524 (2)	0.57867 (19)	0.0329 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.02175 (18)	0.03294 (19)	0.0356 (2)	−0.00587 (13)	−0.00776 (14)	−0.00124 (14)
N1	0.0201 (9)	0.0290 (9)	0.0327 (10)	−0.0066 (7)	−0.0040 (7)	−0.0010 (7)
N2	0.0263 (9)	0.0241 (9)	0.0415 (11)	−0.0077 (7)	−0.0084 (8)	−0.0008 (8)
N3	0.0267 (10)	0.0351 (10)	0.0387 (11)	−0.0079 (8)	−0.0068 (8)	−0.0029 (8)
N4	0.0300 (10)	0.0404 (10)	0.0362 (11)	−0.0080 (8)	−0.0044 (8)	−0.0048 (9)
O1	0.0251 (8)	0.0330 (8)	0.0610 (11)	−0.0081 (7)	−0.0124 (7)	0.0117 (7)
O2	0.0238 (9)	0.0409 (9)	0.0900 (14)	−0.0128 (7)	−0.0162 (9)	0.0134 (9)
O3	0.0240 (8)	0.0351 (8)	0.0431 (9)	−0.0116 (6)	−0.0060 (7)	−0.0026 (7)
O4	0.0276 (8)	0.0280 (8)	0.0585 (11)	−0.0045 (6)	−0.0166 (7)	0.0006 (7)
O5	0.0368 (9)	0.0515 (10)	0.0428 (10)	−0.0209 (8)	−0.0032 (8)	−0.0105 (8)
O6	0.0266 (9)	0.0398 (10)	0.0637 (12)	−0.0115 (7)	−0.0110 (8)	0.0022 (8)
C1	0.0237 (11)	0.0313 (11)	0.0374 (13)	−0.0075 (9)	−0.0050 (9)	−0.0011 (9)
C2	0.0211 (10)	0.0297 (10)	0.0268 (11)	−0.0063 (8)	−0.0028 (8)	−0.0046 (8)
C3	0.0213 (11)	0.0303 (11)	0.0401 (13)	−0.0079 (9)	−0.0066 (9)	−0.0031 (9)
C4	0.0254 (11)	0.0298 (11)	0.0338 (12)	−0.0055 (9)	−0.0067 (9)	−0.0069 (9)
C5	0.0242 (11)	0.0298 (11)	0.0265 (11)	−0.0070 (8)	−0.0030 (9)	−0.0052 (9)
C6	0.0357 (14)	0.0430 (14)	0.0547 (16)	−0.0043 (11)	−0.0076 (12)	−0.0096 (12)
C7	0.0371 (14)	0.0415 (14)	0.077 (2)	−0.0003 (11)	−0.0107 (14)	−0.0080 (14)
C8	0.0368 (14)	0.0400 (14)	0.073 (2)	−0.0092 (11)	−0.0255 (13)	0.0083 (13)
C9	0.0365 (13)	0.0380 (13)	0.0495 (15)	−0.0170 (10)	−0.0175 (11)	0.0083 (11)
C10	0.0535 (16)	0.0579 (16)	0.0433 (16)	−0.0286 (14)	−0.0259 (13)	0.0189 (13)
C11	0.0628 (18)	0.0657 (18)	0.0334 (14)	−0.0306 (15)	−0.0145 (13)	0.0025 (13)
C12	0.0473 (15)	0.0529 (15)	0.0341 (14)	−0.0268 (12)	−0.0046 (11)	−0.0022 (11)
C13	0.0637 (18)	0.0646 (17)	0.0367 (15)	−0.0308 (15)	0.0069 (13)	−0.0155 (13)
C14	0.0529 (17)	0.0530 (16)	0.0520 (17)	−0.0133 (13)	0.0118 (14)	−0.0193 (13)
C15	0.0381 (14)	0.0452 (14)	0.0460 (15)	−0.0065 (11)	−0.0009 (11)	−0.0088 (12)
C16	0.0335 (12)	0.0402 (12)	0.0323 (13)	−0.0184 (10)	−0.0046 (10)	0.0006 (10)
C17	0.0290 (12)	0.0359 (12)	0.0355 (13)	−0.0160 (9)	−0.0076 (10)	0.0034 (10)

Geometric parameters (Å, º) top

Mn1—O1	2.1231 (15)	C2—C3	1.356 (3)
Mn1—O6	2.1439 (15)	C3—C4	1.416 (3)
Mn1—O5	2.1852 (16)	C3—H3	0.9300
Mn1—N1	2.2686 (16)	C6—C7	1.396 (3)
Mn1—N3	2.2880 (18)	C6—H6	0.9300
Mn1—N4	2.2979 (19)	C7—C8	1.356 (4)
N1—C5	1.348 (3)	C7—H7	0.9300
N1—C2	1.366 (2)	C8—C9	1.401 (4)
N2—C4	1.375 (3)	C8—H8	0.9300
N2—C5	1.378 (3)	C9—C17	1.402 (3)
N2—H2	0.8600	C9—C10	1.435 (4)
N3—C6	1.323 (3)	C10—C11	1.344 (4)
N3—C17	1.355 (3)	C10—H10	0.9300
N4—C15	1.323 (3)	C11—C12	1.432 (4)
N4—C16	1.356 (3)	C11—H11	0.9300
O1—C1	1.256 (2)	C12—C13	1.399 (4)
O2—C1	1.229 (2)	C12—C16	1.405 (3)
O3—C5	1.250 (2)	C13—C14	1.362 (4)
O4—C4	1.248 (2)	C13—H13	0.9300
O5—H5A	0.8500	C14—C15	1.392 (4)
O5—H5B	0.8500	C14—H14	0.9300
O6—H6A	0.8499	C15—H15	0.9300
O6—H6B	0.8501	C16—C17	1.442 (3)
C1—C2	1.531 (3)

O1—Mn1—O6	157.87 (6)	O4—C4—N2	119.95 (18)
O1—Mn1—O5	87.31 (6)	O4—C4—C3	125.78 (19)
O6—Mn1—O5	88.81 (6)	N2—C4—C3	114.26 (18)
O1—Mn1—N1	74.55 (6)	O3—C5—N1	123.06 (18)
O6—Mn1—N1	85.75 (6)	O3—C5—N2	118.06 (18)
O5—Mn1—N1	106.65 (6)	N1—C5—N2	118.87 (17)
O1—Mn1—N3	116.16 (6)	N3—C6—C7	122.6 (3)
O6—Mn1—N3	85.65 (6)	N3—C6—H6	118.7
O5—Mn1—N3	90.50 (6)	C7—C6—H6	118.7
N1—Mn1—N3	160.61 (6)	C8—C7—C6	119.6 (3)
O1—Mn1—N4	89.63 (7)	C8—C7—H7	120.2
O6—Mn1—N4	101.40 (7)	C6—C7—H7	120.2
O5—Mn1—N4	159.04 (7)	C7—C8—C9	119.7 (2)
N1—Mn1—N4	92.45 (6)	C7—C8—H8	120.1
N3—Mn1—N4	72.31 (7)	C9—C8—H8	120.1
C5—N1—C2	117.78 (17)	C8—C9—C17	117.0 (2)
C5—N1—Mn1	129.53 (13)	C8—C9—C10	123.6 (2)
C2—N1—Mn1	112.58 (12)	C17—C9—C10	119.4 (2)
C4—N2—C5	125.27 (17)	C11—C10—C9	121.2 (2)
C4—N2—H2	117.4	C11—C10—H10	119.4
C5—N2—H2	117.4	C9—C10—H10	119.4
C6—N3—C17	118.0 (2)	C10—C11—C12	121.0 (2)
C6—N3—Mn1	125.65 (16)	C10—C11—H11	119.5
C17—N3—Mn1	116.18 (14)	C12—C11—H11	119.5
C15—N4—C16	118.1 (2)	C13—C12—C16	117.5 (2)
C15—N4—Mn1	126.10 (16)	C13—C12—C11	123.3 (2)
C16—N4—Mn1	115.76 (15)	C16—C12—C11	119.2 (2)
C1—O1—Mn1	120.96 (13)	C14—C13—C12	120.0 (2)
Mn1—O5—H5A	117.0	C14—C13—H13	120.0
Mn1—O5—H5B	121.2	C12—C13—H13	120.0
H5A—O5—H5B	106.8	C13—C14—C15	118.7 (2)
Mn1—O6—H6A	119.7	C13—C14—H14	120.6
Mn1—O6—H6B	117.1	C15—C14—H14	120.6
H6A—O6—H6B	105.6	N4—C15—C14	123.4 (2)
O2—C1—O1	124.9 (2)	N4—C15—H15	118.3
O2—C1—C2	118.71 (18)	C14—C15—H15	118.3
O1—C1—C2	116.29 (17)	N4—C16—C12	122.2 (2)
C3—C2—N1	124.23 (19)	N4—C16—C17	117.9 (2)
C3—C2—C1	120.98 (18)	C12—C16—C17	119.9 (2)
N1—C2—C1	114.78 (17)	N3—C17—C9	123.0 (2)
C2—C3—C4	119.51 (18)	N3—C17—C16	117.71 (19)
C2—C3—H3	120.2	C9—C17—C16	119.2 (2)
C4—C3—H3	120.2

O1—Mn1—N1—C5	−176.35 (19)	C5—N2—C4—O4	178.6 (2)
O6—Mn1—N1—C5	13.84 (18)	C5—N2—C4—C3	−2.7 (3)
O5—Mn1—N1—C5	101.32 (18)	C2—C3—C4—O4	179.8 (2)
N3—Mn1—N1—C5	−50.0 (3)	C2—C3—C4—N2	1.1 (3)
N4—Mn1—N1—C5	−87.41 (18)	C2—N1—C5—O3	−178.39 (19)
O1—Mn1—N1—C2	7.66 (13)	Mn1—N1—C5—O3	5.8 (3)
O6—Mn1—N1—C2	−162.15 (14)	C2—N1—C5—N2	0.6 (3)
O5—Mn1—N1—C2	−74.67 (14)	Mn1—N1—C5—N2	−175.20 (13)
N3—Mn1—N1—C2	133.99 (19)	C4—N2—C5—O3	−179.11 (19)
N4—Mn1—N1—C2	96.60 (14)	C4—N2—C5—N1	1.8 (3)
O1—Mn1—N3—C6	−101.28 (19)	C17—N3—C6—C7	−1.0 (3)
O6—Mn1—N3—C6	74.74 (19)	Mn1—N3—C6—C7	−175.60 (18)
O5—Mn1—N3—C6	−14.03 (19)	N3—C6—C7—C8	−0.6 (4)
N1—Mn1—N3—C6	138.6 (2)	C6—C7—C8—C9	1.2 (4)
N4—Mn1—N3—C6	178.2 (2)	C7—C8—C9—C17	−0.3 (3)
O1—Mn1—N3—C17	84.04 (15)	C7—C8—C9—C10	−179.7 (2)
O6—Mn1—N3—C17	−99.94 (15)	C8—C9—C10—C11	−179.8 (2)
O5—Mn1—N3—C17	171.29 (15)	C17—C9—C10—C11	0.7 (4)
N1—Mn1—N3—C17	−36.1 (3)	C9—C10—C11—C12	−0.4 (4)
N4—Mn1—N3—C17	3.49 (14)	C10—C11—C12—C13	180.0 (2)
O1—Mn1—N4—C15	60.93 (19)	C10—C11—C12—C16	0.1 (4)
O6—Mn1—N4—C15	−99.75 (19)	C16—C12—C13—C14	−0.5 (4)
O5—Mn1—N4—C15	142.4 (2)	C11—C12—C13—C14	179.6 (2)
N1—Mn1—N4—C15	−13.59 (19)	C12—C13—C14—C15	0.8 (4)
N3—Mn1—N4—C15	178.6 (2)	C16—N4—C15—C14	−0.4 (3)
O1—Mn1—N4—C16	−120.22 (15)	Mn1—N4—C15—C14	178.45 (18)
O6—Mn1—N4—C16	79.11 (15)	C13—C14—C15—N4	−0.4 (4)
O5—Mn1—N4—C16	−38.7 (3)	C15—N4—C16—C12	0.7 (3)
N1—Mn1—N4—C16	165.26 (15)	Mn1—N4—C16—C12	−178.23 (16)
N3—Mn1—N4—C16	−2.52 (14)	C15—N4—C16—C17	−179.66 (19)
O6—Mn1—O1—C1	19.9 (3)	Mn1—N4—C16—C17	1.4 (2)
O5—Mn1—O1—C1	100.05 (18)	C13—C12—C16—N4	−0.3 (3)
N1—Mn1—O1—C1	−8.05 (17)	C11—C12—C16—N4	179.6 (2)
N3—Mn1—O1—C1	−170.71 (16)	C13—C12—C16—C17	−179.9 (2)
N4—Mn1—O1—C1	−100.69 (18)	C11—C12—C16—C17	0.0 (3)
Mn1—O1—C1—O2	−175.75 (19)	C6—N3—C17—C9	2.0 (3)
Mn1—O1—C1—C2	6.9 (3)	Mn1—N3—C17—C9	177.10 (16)
C5—N1—C2—C3	−2.1 (3)	C6—N3—C17—C16	−179.21 (19)
Mn1—N1—C2—C3	174.40 (17)	Mn1—N3—C17—C16	−4.1 (2)
C5—N1—C2—C1	176.54 (18)	C8—C9—C17—N3	−1.4 (3)
Mn1—N1—C2—C1	−7.0 (2)	C10—C9—C17—N3	178.1 (2)
O2—C1—C2—C3	1.8 (3)	C8—C9—C17—C16	179.9 (2)
O1—C1—C2—C3	179.4 (2)	C10—C9—C17—C16	−0.6 (3)
O2—C1—C2—N1	−176.8 (2)	N4—C16—C17—N3	1.8 (3)
O1—C1—C2—N1	0.7 (3)	C12—C16—C17—N3	−178.55 (19)
N1—C2—C3—C4	1.2 (3)	N4—C16—C17—C9	−179.33 (19)
C1—C2—C3—C4	−177.38 (19)	C12—C16—C17—C9	0.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4ⁱ	0.86	1.97	2.831 (2)	177
O5—H5A···O4ⁱⁱ	0.85	2.00	2.829 (2)	164
O5—H5B···O3ⁱⁱⁱ	0.85	1.95	2.769 (2)	162
O6—H6A···O2^iv	0.85	1.79	2.627 (2)	170
O6—H6B···O3	0.85	1.92	2.675 (2)	147

Symmetry codes: (i) −x+1, −y−1, −z+2; (ii) −x+1, −y, −z+2; (iii) −x, −y, −z+2; (iv) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Mn(C₅H₂N₂O₄)(C₁₂H₈N₂)(H₂O)₂]
M_r	425.26
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.3173 (2), 8.9875 (2), 11.9509 (3)
α, β, γ (°)	78.278 (1), 82.910 (1), 74.744 (1)
V (Å³)	841.58 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.83
Crystal size (mm)	0.15 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.886, 0.922
No. of measured, independent and observed [I > 2σ(I)] reflections	9718, 2950, 2539
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.072, 1.05
No. of reflections	2950
No. of parameters	257
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.22

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Mn1—O1	2.1231 (15)	Mn1—N1	2.2686 (16)
Mn1—O6	2.1439 (15)	Mn1—N3	2.2880 (18)
Mn1—O5	2.1852 (16)	Mn1—N4	2.2979 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4ⁱ	0.86	1.97	2.831 (2)	177
O5—H5A···O4ⁱⁱ	0.85	2.00	2.829 (2)	164
O5—H5B···O3ⁱⁱⁱ	0.85	1.95	2.769 (2)	162
O6—H6A···O2^iv	0.85	1.79	2.627 (2)	170
O6—H6B···O3	0.85	1.92	2.675 (2)	147

Symmetry codes: (i) −x+1, −y−1, −z+2; (ii) −x+1, −y, −z+2; (iii) −x, −y, −z+2; (iv) x−1, y, z.

Acknowledgements

The authors thank the Postgraduate Foundation of Taishan University for financial support.

References

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