Poly[[bis­[μ2-8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydro­pyrido[2,3-d]pyrimidine-6-carboxyl­ato]manganese(II)] dihydrate]

Huang, J.; Hu, W.-P.; An, Z.

doi:10.1107/S1600536808006533

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page m547

doi:10.1107/S1600536808006533

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Poly[[bis[μ₂-8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylato]manganese(II)] dihydrate]

Jing Huang,^a Wei-Ping Hu ^b and Zhe An ^a ^*

^aSchool of Pharmaceutical Science, Harbin Medical University, Harbin 150086, People's Republic of China, and ^bSecond Hospital, Harbin Medical University, Harbin 150086, People's Republic of China
^*Correspondence e-mail: anzhe6409@sina.com

(Received 18 February 2008; accepted 8 March 2008; online 14 March 2008)

In the title compound, {[Mn(C₁₄H₁₆N₅O₃)₂]·2H₂O}_n, the Mn^II atom (site symmetry $[\overline{1}]$ ) exhibits a distorted trans-MnN₂O₄ octahedral geometry defined by two monodentate N-bonded and two bidentate O,O′-bonded 8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate anions. An N—H⋯O hydrogen bond is present in the crystal structure. The extended two-dimensional structure is a square grid and the disordered uncoordinated water molecules occupy cavities within the grid.

Related literature

For background, see: Mizuki et al. (1996 ).

Experimental

Crystal data

[Mn(C₁₄H₁₆N₅O₃)₂]·2H₂O
M_r = 695.58
Monoclinic, P 2₁ /c
a = 6.0422 (2) Å
b = 21.5673 (8) Å
c = 12.7395 (5) Å
β = 99.617 (1)°
V = 1636.8 (1) Å³
Z = 2
Mo Kα radiation
μ = 0.47 mm⁻¹
T = 295 (2) K
0.34 × 0.26 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.861, T_max = 0.910
10030 measured reflections
3938 independent reflections
3465 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.191
S = 1.10
3938 reflections
227 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.97 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Selected bond lengths (Å)

Mn1—O1	2.106 (2)
Mn1—O3	2.1667 (16)
Mn1—N5ⁱ	2.372 (2)
Symmetry code: (i) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5N⋯O2ⁱⁱ	0.893 (10)	2.268 (12)	3.149 (3)	169 (3)
Symmetry code: (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808006533/hb2703sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808006533/hb2703Isup2.hkl

checkCIF report

Comment top

Pipemidic acid (Hppa, C₁₄H₁₇N₅O₃, 8-Ethyl-5,8-dihydro-5-oxo-2- (1-piperazinyl)-pyrido(2,3 - d)-pyrimidine-6-carboxylic acid) is member of a class of quinolones used to treat infections (Mizuki et al., 1996). The metal complexes of the ppa anion have not been reported; the title manganese(II) complex, (I), is reported here (Fig. 1).

The Mn^II atom in (I) with site symmetry 1 is coordinated by four oxygen atoms and two N atoms from four ppa ligands (two monodentate-N and two O,O-bidentate) (Table 1) to form a square grid propagating in (Fig. 2). An N—H···O hydrogen bond (Table 2) helps to stabilize this arrangement.

The disordered, uncoordinated, water molecules occupy cavities within the grid. In the present study, their attached H atoms could not be located.

Related literature top

For background, see: Mizuki et al. (1996).

Experimental top

A mixture of Mn(CH₃COO)₂.4H₂O (0.061 g, 0.25 mmol), Hppa (0.15 g, 0.5 mmol), sodium hydroxide (0.04 g, 1 mmol) and water (12 ml) was stirred for 30 min in air. The mixture was then transferred to a 23 ml Teflon-lined hydrothermal bomb. The bomb was kept at 433 K for 72 h under autogenous pressure. Upon cooling, colourless prisms of (I) were obtained from the reaction mixture.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of (I) showing the showing 50% displacement ellipsoids (water molecule O atoms have been omitted for clarity).
	Fig. 2. A view of part of a two-dimensional polymeric sheet in (I) showing the square-grid connectivity (H atoms and water molecule O atoms omitted for clarity).

Poly[[bis[µ₂-8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8- dihydropyrido[2,3-d]pyrimidine-6-carboxylato]manganese(II)] dihydrate] top

Crystal data top

[Mn(C₁₄H₁₆N₅O₃)₂]·2H₂O	F(000) = 718.0
M_r = 695.58	D_x = 1.399 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4747 reflections
a = 6.0422 (2) Å	θ = 2.5–28.3°
b = 21.5673 (8) Å	µ = 0.47 mm⁻¹
c = 12.7395 (5) Å	T = 295 K
β = 99.617 (1)°	Prism, colorless
V = 1636.8 (1) Å³	0.34 × 0.26 × 0.18 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	3938 independent reflections
Radiation source: fine-focus sealed tube	3465 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scans	θ_max = 28.3°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→8
T_min = 0.861, T_max = 0.910	k = −27→28
10030 measured reflections	l = −15→16

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.191	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.1066P)² + 1.0983P] where P = (F_o² + 2F_c²)/3
3938 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.98 e Å⁻³
1 restraint	Δρ_min = −0.48 e Å⁻³

Crystal data top

[Mn(C₁₄H₁₆N₅O₃)₂]·2H₂O	V = 1636.8 (1) Å³
M_r = 695.58	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.0422 (2) Å	µ = 0.47 mm⁻¹
b = 21.5673 (8) Å	T = 295 K
c = 12.7395 (5) Å	0.34 × 0.26 × 0.18 mm
β = 99.617 (1)°

Data collection top

Bruker SMART CCD diffractometer	3938 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3465 reflections with I > 2σ(I)
T_min = 0.861, T_max = 0.910	R_int = 0.019
10030 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	1 restraint
wR(F²) = 0.191	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.98 e Å⁻³
3938 reflections	Δρ_min = −0.48 e Å⁻³
227 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	Occ. (<1)
Mn1	0.5000	0.5000	0.5000	0.02831 (19)
O1W	0.388 (4)	0.5235 (7)	0.9613 (10)	0.244 (9)	0.50
O1	0.7068 (3)	0.49893 (7)	0.38228 (16)	0.0341 (4)
O2W	−0.081 (2)	0.4426 (8)	0.9246 (7)	0.194 (6)	0.50
O2	0.8721 (5)	0.51863 (13)	0.2451 (2)	0.0717 (8)
O3	0.3574 (3)	0.58106 (8)	0.41354 (14)	0.0378 (4)
N1	0.5078 (5)	0.67158 (12)	0.1504 (2)	0.0533 (7)
N2	−0.0007 (4)	0.73723 (11)	0.2985 (2)	0.0464 (6)
N3	0.2395 (4)	0.74681 (10)	0.16596 (18)	0.0432 (5)
N4	−0.0102 (4)	0.82368 (10)	0.19027 (19)	0.0384 (5)
N5	−0.2339 (3)	0.93726 (9)	0.11005 (17)	0.0322 (4)
H5N	−0.140 (4)	0.9649 (12)	0.146 (2)	0.048*
C1	0.7282 (4)	0.52991 (11)	0.3018 (2)	0.0358 (5)
C2	0.5782 (4)	0.58537 (11)	0.2731 (2)	0.0354 (5)
C3	0.4044 (4)	0.60559 (10)	0.33118 (19)	0.0313 (5)
C4	0.2852 (4)	0.66087 (11)	0.28824 (19)	0.0336 (5)
C5	0.1042 (5)	0.68542 (12)	0.3304 (2)	0.0425 (6)
H5A	0.0546	0.6635	0.3848	0.051*
C6	0.0805 (4)	0.76813 (12)	0.2189 (2)	0.0360 (5)
C7	0.3383 (5)	0.69362 (12)	0.2010 (2)	0.0395 (6)
C8	0.6170 (5)	0.61896 (14)	0.1875 (2)	0.0496 (7)
H8A	0.7282	0.6046	0.1512	0.059*
C9	0.5717 (8)	0.7043 (2)	0.0566 (3)	0.0725 (12)
H9A	0.5531	0.7486	0.0645	0.087*
H9B	0.7285	0.6963	0.0537	0.087*
C10	0.4373 (10)	0.6840 (4)	−0.0400 (5)	0.116 (2)
H10A	0.4583	0.6403	−0.0488	0.174*
H10B	0.4811	0.7059	−0.0989	0.174*
H10C	0.2822	0.6923	−0.0375	0.174*
C11	−0.1446 (6)	0.85820 (14)	0.2560 (2)	0.0499 (7)
H11A	−0.0477	0.8852	0.3045	0.060*
H11B	−0.2170	0.8295	0.2980	0.060*
C12	−0.3226 (5)	0.89702 (13)	0.1855 (2)	0.0433 (6)
H12A	−0.4326	0.8693	0.1460	0.052*
H12B	−0.3996	0.9225	0.2308	0.052*
C13	−0.1018 (4)	0.89946 (12)	0.0466 (2)	0.0372 (5)
H13A	−0.0347	0.9264	−0.0003	0.045*
H13B	−0.2015	0.8710	0.0025	0.045*
C14	0.0812 (4)	0.86281 (12)	0.1146 (2)	0.0382 (6)
H14A	0.1573	0.8371	0.0693	0.046*
H14B	0.1906	0.8911	0.1530	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0350 (3)	0.0187 (3)	0.0304 (3)	−0.00041 (16)	0.0030 (2)	0.00255 (16)
O1W	0.47 (3)	0.155 (12)	0.111 (9)	0.000 (15)	0.058 (14)	−0.057 (9)
O1	0.0407 (10)	0.0237 (9)	0.0383 (10)	0.0041 (6)	0.0073 (8)	0.0040 (6)
O2W	0.203 (11)	0.307 (17)	0.088 (6)	−0.110 (12)	0.076 (7)	−0.028 (8)
O2	0.0854 (18)	0.0730 (16)	0.0674 (16)	0.0491 (15)	0.0441 (14)	0.0338 (13)
O3	0.0448 (10)	0.0297 (9)	0.0403 (9)	0.0085 (7)	0.0110 (7)	0.0122 (7)
N1	0.0730 (17)	0.0433 (13)	0.0500 (14)	0.0245 (12)	0.0294 (12)	0.0196 (11)
N2	0.0498 (13)	0.0386 (12)	0.0550 (14)	0.0152 (10)	0.0211 (11)	0.0213 (11)
N3	0.0549 (13)	0.0339 (11)	0.0434 (12)	0.0165 (10)	0.0157 (10)	0.0150 (9)
N4	0.0418 (11)	0.0301 (10)	0.0458 (12)	0.0107 (9)	0.0146 (9)	0.0133 (9)
N5	0.0344 (10)	0.0231 (9)	0.0382 (10)	0.0029 (7)	0.0034 (8)	0.0012 (8)
C1	0.0410 (13)	0.0311 (12)	0.0355 (12)	0.0080 (10)	0.0071 (10)	0.0029 (9)
C2	0.0429 (13)	0.0281 (11)	0.0360 (12)	0.0084 (9)	0.0092 (10)	0.0040 (9)
C3	0.0367 (11)	0.0227 (10)	0.0337 (11)	0.0032 (9)	0.0033 (9)	0.0042 (8)
C4	0.0396 (12)	0.0265 (11)	0.0352 (12)	0.0060 (9)	0.0073 (9)	0.0067 (9)
C5	0.0491 (15)	0.0339 (13)	0.0475 (15)	0.0103 (11)	0.0167 (12)	0.0168 (11)
C6	0.0377 (12)	0.0307 (12)	0.0398 (13)	0.0066 (9)	0.0066 (10)	0.0090 (10)
C7	0.0506 (14)	0.0313 (12)	0.0386 (13)	0.0109 (11)	0.0132 (11)	0.0082 (10)
C8	0.0609 (17)	0.0438 (15)	0.0485 (16)	0.0220 (13)	0.0219 (13)	0.0120 (12)
C9	0.091 (3)	0.071 (2)	0.065 (2)	0.035 (2)	0.041 (2)	0.0293 (19)
C10	0.111 (4)	0.154 (6)	0.085 (4)	0.032 (4)	0.022 (3)	0.021 (4)
C11	0.0604 (17)	0.0465 (15)	0.0478 (15)	0.0251 (14)	0.0234 (13)	0.0176 (13)
C12	0.0427 (13)	0.0368 (13)	0.0535 (16)	0.0129 (11)	0.0169 (12)	0.0133 (12)
C13	0.0394 (13)	0.0308 (12)	0.0414 (13)	0.0087 (10)	0.0071 (10)	0.0078 (10)
C14	0.0365 (12)	0.0304 (12)	0.0497 (14)	0.0075 (9)	0.0128 (11)	0.0136 (10)

Geometric parameters (Å, º) top

Mn1—O1	2.106 (2)	C2—C8	1.361 (4)
Mn1—O1ⁱ	2.106 (2)	C2—C3	1.450 (3)
Mn1—O3	2.1667 (16)	C3—C4	1.452 (3)
Mn1—O3ⁱ	2.1667 (16)	C4—C7	1.399 (3)
Mn1—N5ⁱⁱ	2.372 (2)	C4—C5	1.400 (4)
Mn1—N5ⁱⁱⁱ	2.3723 (19)	C5—H5A	0.9300
O1—C1	1.248 (3)	C8—H8A	0.9300
O2—C1	1.244 (3)	C9—C10	1.425 (8)
O3—C3	1.249 (3)	C9—H9A	0.9700
N1—C8	1.357 (3)	C9—H9B	0.9700
N1—C7	1.382 (4)	C10—H10A	0.9600
N1—C9	1.493 (4)	C10—H10B	0.9600
N2—C5	1.315 (3)	C10—H10C	0.9600
N2—C6	1.371 (4)	C11—C12	1.531 (4)
N3—C7	1.335 (3)	C11—H11A	0.9700
N3—C6	1.344 (3)	C11—H11B	0.9700
N4—C6	1.343 (3)	C12—H12A	0.9700
N4—C14	1.457 (3)	C12—H12B	0.9700
N4—C11	1.463 (3)	C13—C14	1.510 (3)
N5—C12	1.461 (3)	C13—H13A	0.9700
N5—C13	1.474 (3)	C13—H13B	0.9700
N5—Mn1^iv	2.3723 (19)	C14—H14A	0.9700
N5—H5N	0.90 (3)	C14—H14B	0.9700
C1—C2	1.508 (3)

O1—Mn1—O1ⁱ	180.0	N4—C6—N3	117.5 (2)
O1—Mn1—O3	83.09 (6)	N4—C6—N2	117.0 (2)
O1ⁱ—Mn1—O3	96.91 (6)	N3—C6—N2	125.4 (2)
O1—Mn1—O3ⁱ	96.91 (6)	N3—C7—N1	117.7 (2)
O1ⁱ—Mn1—O3ⁱ	83.09 (6)	N3—C7—C4	123.4 (2)
O3—Mn1—O3ⁱ	180.0	N1—C7—C4	118.9 (2)
O1—Mn1—N5ⁱⁱ	90.17 (7)	N1—C8—C2	125.8 (3)
O1ⁱ—Mn1—N5ⁱⁱ	89.83 (7)	N1—C8—H8A	117.1
O3—Mn1—N5ⁱⁱ	90.74 (7)	C2—C8—H8A	117.1
O3ⁱ—Mn1—N5ⁱⁱ	89.26 (7)	C10—C9—N1	111.2 (5)
O1—Mn1—N5ⁱⁱⁱ	89.83 (7)	C10—C9—H9A	109.4
O1ⁱ—Mn1—N5ⁱⁱⁱ	90.17 (7)	N1—C9—H9A	109.4
O3—Mn1—N5ⁱⁱⁱ	89.26 (7)	C10—C9—H9B	109.4
O3ⁱ—Mn1—N5ⁱⁱⁱ	90.73 (7)	N1—C9—H9B	109.4
N5ⁱⁱ—Mn1—N5ⁱⁱⁱ	180.0	H9A—C9—H9B	108.0
C1—O1—Mn1	137.22 (16)	C9—C10—H10A	109.5
C3—O3—Mn1	129.93 (16)	C9—C10—H10B	109.5
C8—N1—C7	118.7 (2)	H10A—C10—H10B	109.5
C8—N1—C9	119.8 (3)	C9—C10—H10C	109.5
C7—N1—C9	121.4 (2)	H10A—C10—H10C	109.5
C5—N2—C6	115.3 (2)	H10B—C10—H10C	109.5
C7—N3—C6	116.3 (2)	N4—C11—C12	110.2 (2)
C6—N4—C14	120.9 (2)	N4—C11—H11A	109.6
C6—N4—C11	122.6 (2)	C12—C11—H11A	109.6
C14—N4—C11	113.1 (2)	N4—C11—H11B	109.6
C12—N5—C13	108.90 (19)	C12—C11—H11B	109.6
C12—N5—Mn1^iv	116.15 (15)	H11A—C11—H11B	108.1
C13—N5—Mn1^iv	111.54 (14)	N5—C12—C11	114.3 (2)
C12—N5—H5N	110 (2)	N5—C12—H12A	108.7
C13—N5—H5N	107 (2)	C11—C12—H12A	108.7
Mn1^iv—N5—H5N	103 (2)	N5—C12—H12B	108.7
O2—C1—O1	123.4 (2)	C11—C12—H12B	108.7
O2—C1—C2	117.6 (2)	H12A—C12—H12B	107.6
O1—C1—C2	118.9 (2)	N5—C13—C14	112.8 (2)
C8—C2—C3	119.0 (2)	N5—C13—H13A	109.0
C8—C2—C1	116.1 (2)	C14—C13—H13A	109.0
C3—C2—C1	124.9 (2)	N5—C13—H13B	109.0
O3—C3—C2	126.0 (2)	C14—C13—H13B	109.0
O3—C3—C4	119.8 (2)	H13A—C13—H13B	107.8
C2—C3—C4	114.3 (2)	N4—C14—C13	111.1 (2)
C7—C4—C5	114.3 (2)	N4—C14—H14A	109.4
C7—C4—C3	123.3 (2)	C13—C14—H14A	109.4
C5—C4—C3	122.4 (2)	N4—C14—H14B	109.4
N2—C5—C4	124.8 (2)	C13—C14—H14B	109.4
N2—C5—H5A	117.6	H14A—C14—H14B	108.0
C4—C5—H5A	117.6

O3—Mn1—O1—C1	−1.4 (3)	C7—N3—C6—N4	175.3 (3)
O3ⁱ—Mn1—O1—C1	178.6 (3)	C7—N3—C6—N2	−6.2 (4)
N5ⁱⁱ—Mn1—O1—C1	−92.1 (3)	C5—N2—C6—N4	−174.7 (3)
N5ⁱⁱⁱ—Mn1—O1—C1	87.9 (3)	C5—N2—C6—N3	6.8 (4)
O1—Mn1—O3—C3	1.4 (2)	C6—N3—C7—N1	−177.9 (3)
O1ⁱ—Mn1—O3—C3	−178.6 (2)	C6—N3—C7—C4	−0.5 (4)
N5ⁱⁱ—Mn1—O3—C3	91.5 (2)	C8—N1—C7—N3	177.3 (3)
N5ⁱⁱⁱ—Mn1—O3—C3	−88.5 (2)	C9—N1—C7—N3	−2.9 (5)
Mn1—O1—C1—O2	179.3 (2)	C8—N1—C7—C4	−0.1 (5)
Mn1—O1—C1—C2	1.5 (4)	C9—N1—C7—C4	179.7 (3)
O2—C1—C2—C8	−1.0 (4)	C5—C4—C7—N3	5.6 (4)
O1—C1—C2—C8	177.0 (3)	C3—C4—C7—N3	−175.2 (3)
O2—C1—C2—C3	−179.1 (3)	C5—C4—C7—N1	−177.1 (3)
O1—C1—C2—C3	−1.2 (4)	C3—C4—C7—N1	2.1 (4)
Mn1—O3—C3—C2	−1.8 (4)	C7—N1—C8—C2	−1.3 (5)
Mn1—O3—C3—C4	−179.39 (16)	C9—N1—C8—C2	178.8 (4)
C8—C2—C3—O3	−176.6 (3)	C3—C2—C8—N1	0.8 (5)
C1—C2—C3—O3	1.5 (4)	C1—C2—C8—N1	−177.5 (3)
C8—C2—C3—C4	1.1 (4)	C8—N1—C9—C10	92.7 (5)
C1—C2—C3—C4	179.2 (2)	C7—N1—C9—C10	−87.1 (5)
O3—C3—C4—C7	175.3 (2)	C6—N4—C11—C12	−148.9 (3)
C2—C3—C4—C7	−2.5 (4)	C14—N4—C11—C12	51.9 (3)
O3—C3—C4—C5	−5.6 (4)	C13—N5—C12—C11	54.0 (3)
C2—C3—C4—C5	176.6 (3)	Mn1^iv—N5—C12—C11	−179.1 (2)
C6—N2—C5—C4	−0.7 (5)	N4—C11—C12—N5	−52.9 (4)
C7—C4—C5—N2	−5.0 (4)	C12—N5—C13—C14	−55.0 (3)
C3—C4—C5—N2	175.8 (3)	Mn1^iv—N5—C13—C14	175.47 (16)
C14—N4—C6—N3	−8.0 (4)	C6—N4—C14—C13	146.2 (3)
C11—N4—C6—N3	−165.6 (3)	C11—N4—C14—C13	−54.2 (3)
C14—N4—C6—N2	173.4 (3)	N5—C13—C14—N4	55.9 (3)
C11—N4—C6—N2	15.8 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, −y+3/2, z+1/2; (iii) −x, y−1/2, −z+1/2; (iv) −x, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···O2^v	0.89 (1)	2.27 (1)	3.149 (3)	169 (3)

Symmetry code: (v) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Mn(C₁₄H₁₆N₅O₃)₂]·2H₂O
M_r	695.58
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	6.0422 (2), 21.5673 (8), 12.7395 (5)
β (°)	99.617 (1)
V (Å³)	1636.8 (1)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.47
Crystal size (mm)	0.34 × 0.26 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.861, 0.910
No. of measured, independent and observed [I > 2σ(I)] reflections	10030, 3938, 3465
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.191, 1.11
No. of reflections	3938
No. of parameters	227
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.98, −0.48

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Mn1—O1	2.106 (2)	Mn1—N5ⁱ	2.372 (2)
Mn1—O3	2.1667 (16)

Symmetry code: (i) x+1, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···O2ⁱⁱ	0.893 (10)	2.268 (12)	3.149 (3)	169 (3)

Symmetry code: (ii) −x+1, y+1/2, −z+1/2.

Acknowledgements

The authors thank the Innovation Science Foundation of Harbin Medical University for financial support (grant No. 060041).

References

Bruker (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Mizuki, Y., Fujiwara, I. & Yamaguchi, T. (1996). J. Antimicrob. Chemother. Suppl. A, 37, 41–45. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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