Poly[aqua­bis(μ4-naphthalene-1,4-di­carboxyl­ato)(1,10-phenanthroline-5,6-dione)dimanganese(II)]

Cong, F.-D.; Yu, F.-Y.; Wei, Z.; Ng, S.W.

doi:10.1107/S1600536809046388

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1543

doi:10.1107/S1600536809046388

Open

access

Poly[aquabis(μ₄-naphthalene-1,4-dicarboxylato)(1,10-phenanthroline-5,6-dione)dimanganese(II)]

Fang-Di Cong,^a ^* Feng-Yang Yu,^a Zhen Wei ^a and Seik Weng Ng ^b

^aDepartment of Basic Science, Tianjin Agricultural University, Tjianjin 300384, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: congfangdi666@yahoo.com.cn

(Received 1 November 2009; accepted 4 November 2009; online 7 November 2009)

The three-dimensional coordination polymer, [Mn₂(C₁₂H₆O₄)₂(C₁₂H₆N₂O₂)(H₂O)]_n, features a water-coordinated Mn^II ion and an N-heterocycle-chelated Mn^II ion, both in six-coordinate octahedral geometries. Of the two rigid dianions, one is bonded to four Mn^II ions, with each of the O atoms being connected to a different metal ion. The other dianion uses one carboxylate group to chelate to one Mn^II ion and its other carboxylate group to bind to two Mn^II ions.

Related literature

For similiar manganese naphthalene-1,4-dicarboxylate polymers, see: Boeckmann et al. (2009 ); Li et al. (2008 ).

Experimental

Crystal data

[Mn₂(C₁₂H₆O₄)₂(C₁₂H₆N₂O₂)(H₂O)]
M_r = 766.42
Monoclinic, P 2₁ /c
a = 8.4393 (8) Å
b = 19.2477 (18) Å
c = 19.2504 (19) Å
β = 101.781 (1)°
V = 3061.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.90 mm⁻¹
T = 293 K
0.27 × 0.26 × 0.20 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.794, T_max = 0.841
16986 measured reflections
6015 independent reflections
4853 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.096
S = 1.03
6015 reflections
466 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Selected bond lengths (Å)

Mn1—O1	2.106 (2)
Mn1—O4ⁱ	2.137 (2)
Mn1—O5	2.190 (2)
Mn1—O6	2.545 (2)
Mn1—O7ⁱⁱ	2.182 (2)
Mn1—O1W	2.157 (2)
Mn2—O2	2.125 (2)
Mn2—O3ⁱⁱⁱ	2.173 (2)
Mn2—O5	2.192 (2)
Mn2—O8ⁱⁱ	2.104 (2)
Mn2—N1	2.273 (2)
Mn2—N2	2.268 (2)
Symmetry codes: (i) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046388/ci2963sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809046388/ci2963Isup2.hkl

checkCIF report

Related literature top

For similiar manganese naphthalene-1,4-dicarboxylate polymers, see: Boeckmann et al. (2009); Li et al. (2008).

Experimental top

Manganese dichloride tetrahydrate (0.5 mmol, 0.099 g), naphthalene-1,4-dicarboxylic acid (0.5 mmol, 0.108 g), phenanthrene-9,10-dione (0.5 mmol, 0.104 g) and water (12 ml) were heated in a Teflon-lined, stainless-steel Parr bomb at 433 K for 3 days. Yellow crystals were isolated from the cool bomb in 40% yield.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of a part of the polymeric three-dimensional structure of Mn₂(H₂O)(C₁₂H₆O₄)₂(C₁₂H₆N₂O₂) at the 50% probability level; H atoms are drawn as spheres of arbitrary radius. Symmetry codes are given in Table 1.

Poly[aquabis(µ₄-naphthalene-1,4-dicarboxylato)(1,10-phenanthroline- 5,6-dione)dimanganese(II)] top

Crystal data top

[Mn₂(C₁₂H₆O₄)₂(C₁₂H₆N₂O₂)(H₂O)]	F(000) = 1552
M_r = 766.42	D_x = 1.663 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5446 reflections
a = 8.4393 (8) Å	θ = 2.1–25.7°
b = 19.2477 (18) Å	µ = 0.90 mm⁻¹
c = 19.2504 (19) Å	T = 293 K
β = 101.781 (1)°	Block, yellow
V = 3061.1 (5) Å³	0.27 × 0.26 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	6015 independent reflections
Radiation source: fine-focus sealed tube	4853 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 26.1°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.794, T_max = 0.841	k = −15→23
16986 measured reflections	l = −23→22

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0581P)² + 0.1115P] where P = (F_o² + 2F_c²)/3
6015 reflections	(Δ/σ)_max = 0.001
466 parameters	Δρ_max = 0.40 e Å⁻³
3 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

[Mn₂(C₁₂H₆O₄)₂(C₁₂H₆N₂O₂)(H₂O)]	V = 3061.1 (5) Å³
M_r = 766.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.4393 (8) Å	µ = 0.90 mm⁻¹
b = 19.2477 (18) Å	T = 293 K
c = 19.2504 (19) Å	0.27 × 0.26 × 0.20 mm
β = 101.781 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	6015 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4853 reflections with I > 2σ(I)
T_min = 0.794, T_max = 0.841	R_int = 0.025
16986 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	3 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.40 e Å⁻³
6015 reflections	Δρ_min = −0.24 e Å⁻³
466 parameters

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

	x	y	z	U_iso*/U_eq
Mn1	0.67563 (4)	0.723418 (17)	0.635261 (16)	0.02973 (10)
Mn2	0.32185 (4)	0.688473 (16)	0.694983 (16)	0.02825 (10)
O1	0.49411 (18)	0.71363 (9)	0.54284 (8)	0.0435 (4)
O2	0.2654 (2)	0.69971 (10)	0.58282 (8)	0.0491 (4)
O3	0.09036 (18)	0.76369 (9)	0.19849 (8)	0.0381 (4)
O4	−0.14651 (18)	0.76639 (9)	0.23115 (8)	0.0448 (4)
O5	0.55827 (18)	0.64436 (7)	0.68920 (9)	0.0371 (4)
O6	0.7185 (2)	0.59280 (10)	0.63001 (11)	0.0591 (5)
O7	0.4054 (2)	0.32857 (10)	0.84788 (10)	0.0574 (5)
O8	0.5400 (2)	0.27848 (8)	0.77449 (11)	0.0557 (5)
O9	0.0460 (3)	0.40503 (13)	0.83873 (16)	0.1069 (9)
O10	0.2619 (3)	0.45832 (15)	0.95212 (15)	0.1063 (10)
O1W	0.8607 (2)	0.75106 (16)	0.57777 (10)	0.0787 (7)
H1W1	0.949 (3)	0.754 (2)	0.6082 (16)	0.118*
H1W2	0.851 (4)	0.7853 (14)	0.5499 (17)	0.118*
N1	0.1895 (2)	0.58539 (10)	0.69258 (11)	0.0396 (5)
N2	0.3748 (2)	0.64538 (10)	0.80699 (10)	0.0356 (4)
C1	0.3440 (3)	0.71125 (12)	0.53511 (11)	0.0334 (5)
C2	0.2493 (2)	0.72461 (11)	0.46106 (11)	0.0306 (5)
C3	0.2775 (3)	0.68379 (11)	0.40590 (11)	0.0328 (5)
H3	0.3502	0.6470	0.4151	0.039*
C4	0.1973 (2)	0.69744 (11)	0.33599 (11)	0.0303 (5)
H4	0.2198	0.6703	0.2993	0.036*
C5	0.0864 (2)	0.74994 (12)	0.32073 (10)	0.0291 (5)
C6	0.0551 (2)	0.79415 (12)	0.37652 (11)	0.0312 (5)
C7	0.1407 (2)	0.78174 (11)	0.44707 (11)	0.0310 (5)
C8	0.1222 (3)	0.82974 (13)	0.50106 (12)	0.0406 (6)
H8	0.1785	0.8225	0.5473	0.049*
C9	0.0237 (3)	0.88607 (14)	0.48629 (14)	0.0512 (7)
H9	0.0149	0.9174	0.5221	0.061*
C10	−0.0644 (3)	0.89695 (15)	0.41734 (14)	0.0543 (7)
H10	−0.1336	0.9349	0.4079	0.065*
C11	−0.0502 (3)	0.85250 (13)	0.36358 (13)	0.0434 (6)
H11	−0.1099	0.8605	0.3181	0.052*
C12	0.0036 (3)	0.76148 (11)	0.24480 (11)	0.0303 (5)
C13	0.6211 (3)	0.58948 (11)	0.66943 (12)	0.0335 (5)
C14	0.5764 (3)	0.52226 (11)	0.69999 (12)	0.0352 (5)
C15	0.6256 (3)	0.51188 (12)	0.77124 (13)	0.0437 (6)
H15	0.6830	0.5467	0.7990	0.052*
C16	0.5917 (3)	0.44982 (12)	0.80367 (13)	0.0410 (6)
H16	0.6303	0.4433	0.8520	0.049*
C17	0.5020 (3)	0.39879 (11)	0.76437 (12)	0.0341 (5)
C18	0.4411 (3)	0.40882 (11)	0.69041 (12)	0.0342 (5)
C19	0.4819 (3)	0.47085 (11)	0.65730 (12)	0.0347 (5)
C20	0.4218 (3)	0.47993 (14)	0.58366 (13)	0.0462 (6)
H20	0.4474	0.5201	0.5614	0.055*
C21	0.3261 (3)	0.43017 (15)	0.54474 (14)	0.0551 (7)
H21	0.2903	0.4361	0.4961	0.066*
C22	0.2825 (3)	0.37081 (15)	0.57776 (15)	0.0556 (7)
H22	0.2150	0.3381	0.5510	0.067*
C23	0.3369 (3)	0.35979 (13)	0.64828 (14)	0.0461 (6)
H23	0.3058	0.3199	0.6693	0.055*
C24	0.4799 (3)	0.33048 (12)	0.79864 (13)	0.0393 (5)
C25	0.0982 (3)	0.55711 (14)	0.63501 (15)	0.0518 (7)
H25	0.0897	0.5800	0.5919	0.062*
C26	0.0150 (3)	0.49487 (16)	0.63629 (19)	0.0671 (9)
H26	−0.0466	0.4762	0.5949	0.081*
C27	0.0261 (4)	0.46209 (15)	0.6996 (2)	0.0687 (9)
H27	−0.0283	0.4204	0.7019	0.082*
C28	0.1182 (3)	0.49066 (13)	0.76087 (17)	0.0523 (7)
C29	0.1999 (3)	0.55246 (11)	0.75504 (13)	0.0383 (5)
C30	0.1294 (4)	0.45708 (16)	0.8302 (2)	0.0719 (10)
C31	0.2429 (3)	0.48801 (17)	0.89331 (19)	0.0677 (9)
C32	0.3262 (3)	0.55354 (14)	0.88447 (15)	0.0497 (7)
C33	0.3028 (3)	0.58499 (12)	0.81738 (13)	0.0377 (5)
C34	0.4268 (4)	0.58562 (17)	0.94055 (15)	0.0600 (8)
H34	0.4424	0.5663	0.9857	0.072*
C35	0.5043 (3)	0.64632 (16)	0.92973 (14)	0.0558 (7)
H35	0.5750	0.6679	0.9668	0.067*
C36	0.4743 (3)	0.67442 (13)	0.86218 (13)	0.0436 (6)
H36	0.5261	0.7156	0.8548	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.02579 (17)	0.0373 (2)	0.02387 (18)	−0.00187 (13)	−0.00003 (13)	0.00353 (13)
Mn2	0.02932 (18)	0.02970 (19)	0.02565 (18)	−0.00156 (13)	0.00545 (13)	0.00262 (13)
O1	0.0295 (8)	0.0699 (12)	0.0270 (9)	0.0000 (8)	−0.0040 (7)	0.0044 (8)
O2	0.0406 (9)	0.0801 (13)	0.0252 (9)	0.0001 (9)	0.0033 (7)	0.0107 (8)
O3	0.0312 (8)	0.0585 (11)	0.0239 (8)	−0.0072 (7)	0.0039 (6)	0.0004 (7)
O4	0.0277 (8)	0.0786 (13)	0.0251 (8)	0.0072 (8)	−0.0019 (6)	0.0002 (8)
O5	0.0374 (8)	0.0267 (8)	0.0477 (10)	0.0047 (6)	0.0099 (7)	0.0071 (7)
O6	0.0663 (12)	0.0533 (12)	0.0682 (13)	0.0105 (9)	0.0383 (11)	0.0109 (9)
O7	0.0712 (13)	0.0504 (11)	0.0552 (12)	−0.0088 (9)	0.0237 (10)	0.0068 (9)
O8	0.0668 (12)	0.0262 (9)	0.0721 (13)	0.0113 (8)	0.0099 (10)	0.0051 (8)
O9	0.114 (2)	0.0741 (17)	0.139 (3)	−0.0251 (15)	0.0409 (19)	0.0406 (16)
O10	0.0751 (16)	0.128 (2)	0.116 (2)	0.0035 (15)	0.0201 (15)	0.0892 (19)
O1W	0.0413 (11)	0.160 (2)	0.0328 (11)	−0.0267 (13)	0.0040 (9)	0.0165 (12)
N1	0.0353 (10)	0.0389 (11)	0.0448 (12)	−0.0035 (8)	0.0086 (9)	−0.0023 (9)
N2	0.0357 (10)	0.0387 (11)	0.0330 (11)	0.0031 (8)	0.0083 (8)	0.0026 (8)
C1	0.0356 (12)	0.0398 (13)	0.0233 (11)	0.0000 (9)	0.0026 (9)	0.0007 (9)
C2	0.0242 (10)	0.0420 (13)	0.0235 (11)	−0.0037 (9)	−0.0001 (8)	0.0032 (9)
C3	0.0305 (11)	0.0364 (13)	0.0293 (12)	0.0020 (9)	0.0007 (9)	0.0014 (9)
C4	0.0304 (11)	0.0338 (12)	0.0252 (11)	−0.0024 (9)	0.0020 (9)	−0.0028 (9)
C5	0.0248 (10)	0.0380 (12)	0.0226 (11)	−0.0055 (9)	0.0001 (8)	0.0018 (9)
C6	0.0232 (10)	0.0442 (13)	0.0258 (11)	0.0001 (9)	0.0037 (8)	0.0008 (9)
C7	0.0240 (10)	0.0448 (14)	0.0236 (11)	−0.0022 (9)	0.0038 (8)	0.0021 (9)
C8	0.0403 (13)	0.0570 (16)	0.0241 (12)	0.0035 (11)	0.0055 (10)	−0.0014 (10)
C9	0.0518 (15)	0.0654 (18)	0.0377 (15)	0.0130 (13)	0.0122 (12)	−0.0118 (12)
C10	0.0486 (15)	0.0658 (19)	0.0469 (16)	0.0253 (13)	0.0062 (12)	−0.0052 (13)
C11	0.0372 (12)	0.0580 (17)	0.0318 (13)	0.0132 (11)	−0.0002 (10)	0.0000 (11)
C12	0.0310 (11)	0.0355 (12)	0.0219 (11)	−0.0039 (9)	−0.0004 (9)	−0.0004 (9)
C13	0.0337 (11)	0.0319 (12)	0.0332 (12)	0.0033 (9)	0.0031 (10)	0.0039 (9)
C14	0.0400 (12)	0.0270 (12)	0.0389 (13)	0.0067 (9)	0.0091 (10)	0.0036 (9)
C15	0.0567 (15)	0.0306 (13)	0.0404 (14)	−0.0062 (11)	0.0019 (12)	−0.0007 (10)
C16	0.0550 (15)	0.0309 (13)	0.0340 (13)	−0.0014 (11)	0.0022 (11)	0.0038 (10)
C17	0.0378 (12)	0.0262 (12)	0.0384 (13)	0.0066 (9)	0.0077 (10)	0.0020 (9)
C18	0.0360 (12)	0.0272 (12)	0.0388 (13)	0.0066 (9)	0.0062 (10)	−0.0024 (10)
C19	0.0380 (12)	0.0298 (12)	0.0363 (13)	0.0097 (9)	0.0078 (10)	−0.0004 (10)
C20	0.0523 (15)	0.0468 (15)	0.0387 (14)	0.0083 (12)	0.0073 (12)	0.0026 (11)
C21	0.0618 (17)	0.0634 (19)	0.0360 (15)	0.0086 (14)	0.0007 (13)	−0.0053 (13)
C22	0.0544 (16)	0.0535 (17)	0.0525 (17)	0.0014 (13)	−0.0044 (13)	−0.0174 (14)
C23	0.0445 (14)	0.0357 (14)	0.0539 (16)	0.0023 (11)	0.0002 (12)	−0.0077 (11)
C24	0.0377 (12)	0.0315 (13)	0.0448 (15)	−0.0028 (10)	−0.0008 (11)	0.0046 (11)
C25	0.0448 (14)	0.0533 (17)	0.0558 (17)	−0.0035 (12)	0.0062 (13)	−0.0083 (13)
C26	0.0498 (16)	0.0559 (19)	0.091 (3)	−0.0129 (14)	0.0027 (16)	−0.0235 (18)
C27	0.0528 (17)	0.0409 (17)	0.112 (3)	−0.0162 (13)	0.0163 (18)	−0.0035 (18)
C28	0.0421 (14)	0.0373 (14)	0.082 (2)	−0.0015 (11)	0.0219 (14)	0.0063 (14)
C29	0.0315 (11)	0.0315 (12)	0.0556 (16)	0.0040 (9)	0.0176 (11)	0.0029 (11)
C30	0.0629 (19)	0.0480 (18)	0.113 (3)	0.0073 (15)	0.038 (2)	0.0318 (18)
C31	0.0480 (16)	0.072 (2)	0.089 (2)	0.0135 (15)	0.0276 (16)	0.0460 (19)
C32	0.0446 (14)	0.0553 (17)	0.0543 (17)	0.0139 (12)	0.0216 (13)	0.0246 (13)
C33	0.0342 (12)	0.0353 (13)	0.0478 (14)	0.0081 (10)	0.0179 (11)	0.0093 (11)
C34	0.0582 (17)	0.080 (2)	0.0435 (16)	0.0232 (16)	0.0148 (14)	0.0234 (15)
C35	0.0564 (17)	0.070 (2)	0.0379 (15)	0.0158 (15)	0.0016 (13)	0.0003 (13)
C36	0.0443 (14)	0.0463 (15)	0.0389 (14)	0.0045 (11)	0.0057 (11)	−0.0002 (11)

Geometric parameters (Å, º) top

Mn1—O1	2.106 (2)	C8—C9	1.361 (4)
Mn1—O4ⁱ	2.137 (2)	C8—H8	0.93
Mn1—O5	2.190 (2)	C9—C10	1.398 (4)
Mn1—O6	2.545 (2)	C9—H9	0.93
Mn1—O7ⁱⁱ	2.182 (2)	C10—C11	1.367 (3)
Mn1—O1W	2.157 (2)	C10—H10	0.93
Mn2—O2	2.125 (2)	C11—H11	0.93
Mn2—O3ⁱⁱⁱ	2.173 (2)	C13—C14	1.501 (3)
Mn2—O5	2.192 (2)	C14—C15	1.364 (3)
Mn2—O8ⁱⁱ	2.104 (2)	C14—C19	1.422 (3)
Mn2—N1	2.273 (2)	C15—C16	1.404 (3)
Mn2—N2	2.268 (2)	C15—H15	0.93
O1—C1	1.246 (3)	C16—C17	1.370 (3)
O2—C1	1.258 (3)	C16—H16	0.93
O3—C12	1.265 (2)	C17—C18	1.425 (3)
O3—Mn2^iv	2.1733 (15)	C17—C24	1.500 (3)
O4—C12	1.244 (3)	C18—C23	1.425 (3)
O4—Mn1^v	2.1371 (15)	C18—C19	1.428 (3)
O5—C13	1.274 (3)	C19—C20	1.416 (3)
O6—C13	1.229 (3)	C20—C21	1.373 (4)
O7—C24	1.240 (3)	C20—H20	0.93
O7—Mn1^vi	2.1818 (18)	C21—C22	1.393 (4)
O8—C24	1.254 (3)	C21—H21	0.93
O8—Mn2^vi	2.1039 (17)	C22—C23	1.358 (4)
O9—C30	1.254 (4)	C22—H22	0.93
O10—C31	1.249 (4)	C23—H23	0.93
O1W—H1W1	0.852 (10)	C25—C26	1.392 (4)
O1W—H1W2	0.844 (10)	C25—H25	0.93
N1—C25	1.330 (3)	C26—C27	1.359 (5)
N1—C29	1.346 (3)	C26—H26	0.93
N2—C36	1.335 (3)	C27—C28	1.387 (4)
N2—C33	1.346 (3)	C27—H27	0.93
C1—C2	1.507 (3)	C28—C29	1.391 (3)
C2—C3	1.380 (3)	C28—C30	1.469 (4)
C2—C7	1.421 (3)	C29—C33	1.470 (3)
C3—C4	1.403 (3)	C30—C31	1.507 (5)
C3—H3	0.93	C31—C32	1.471 (4)
C4—C5	1.367 (3)	C32—C34	1.376 (4)
C4—H4	0.93	C32—C33	1.403 (3)
C5—C6	1.436 (3)	C34—C35	1.375 (4)
C5—C12	1.502 (3)	C34—H34	0.93
C6—C7	1.422 (3)	C35—C36	1.383 (4)
C6—C11	1.422 (3)	C35—H35	0.93
C7—C8	1.423 (3)	C36—H36	0.93

O1—Mn1—O4ⁱ	178.03 (6)	O4—C12—O3	124.03 (19)
O1—Mn1—O1W	93.82 (7)	O4—C12—C5	117.92 (18)
O4ⁱ—Mn1—O1W	88.06 (7)	O3—C12—C5	118.02 (18)
O1—Mn1—O7ⁱⁱ	90.73 (7)	O6—C13—O5	120.8 (2)
O4ⁱ—Mn1—O7ⁱⁱ	88.43 (7)	O6—C13—C14	122.7 (2)
O1W—Mn1—O7ⁱⁱ	97.43 (10)	O5—C13—C14	116.39 (19)
O1—Mn1—O5	90.97 (6)	C15—C14—C19	119.9 (2)
O4ⁱ—Mn1—O5	87.72 (6)	C15—C14—C13	118.1 (2)
O1W—Mn1—O5	149.28 (9)	C19—C14—C13	122.0 (2)
O7ⁱⁱ—Mn1—O5	112.85 (6)	C14—C15—C16	121.6 (2)
O8ⁱⁱ—Mn2—O2	101.33 (7)	C14—C15—H15	119.2
O8ⁱⁱ—Mn2—O3ⁱⁱⁱ	95.33 (7)	C16—C15—H15	119.2
O2—Mn2—O3ⁱⁱⁱ	88.39 (6)	C17—C16—C15	120.3 (2)
O8ⁱⁱ—Mn2—O5	82.81 (7)	C17—C16—H16	119.9
O2—Mn2—O5	90.31 (6)	C15—C16—H16	119.9
O3ⁱⁱⁱ—Mn2—O5	177.48 (6)	C16—C17—C18	120.0 (2)
O8ⁱⁱ—Mn2—N2	92.59 (7)	C16—C17—C24	119.4 (2)
O2—Mn2—N2	164.37 (7)	C18—C17—C24	120.4 (2)
O3ⁱⁱⁱ—Mn2—N2	97.43 (6)	C17—C18—C23	122.3 (2)
O5—Mn2—N2	84.37 (6)	C17—C18—C19	119.3 (2)
O8ⁱⁱ—Mn2—N1	165.15 (8)	C23—C18—C19	118.5 (2)
O2—Mn2—N1	93.49 (7)	C20—C19—C14	122.5 (2)
O3ⁱⁱⁱ—Mn2—N1	85.94 (7)	C20—C19—C18	118.7 (2)
O5—Mn2—N1	96.29 (6)	C14—C19—C18	118.8 (2)
N2—Mn2—N1	72.58 (7)	C21—C20—C19	120.7 (2)
C1—O1—Mn1	130.60 (14)	C21—C20—H20	119.6
C1—O2—Mn2	135.86 (15)	C19—C20—H20	119.6
C12—O3—Mn2^iv	133.60 (14)	C20—C21—C22	120.3 (3)
C12—O4—Mn1^v	134.03 (14)	C20—C21—H21	119.9
C13—O5—Mn1	100.28 (13)	C22—C21—H21	119.9
C13—O5—Mn2	140.78 (14)	C23—C22—C21	121.2 (3)
Mn1—O5—Mn2	105.04 (6)	C23—C22—H22	119.4
C24—O7—Mn1^vi	111.36 (16)	C21—C22—H22	119.4
C24—O8—Mn2^vi	142.85 (18)	C22—C23—C18	120.6 (3)
Mn1—O1W—H1W1	107 (3)	C22—C23—H23	119.7
Mn1—O1W—H1W2	122 (3)	C18—C23—H23	119.7
H1W1—O1W—H1W2	110.1 (17)	O7—C24—O8	124.5 (2)
C25—N1—C29	118.2 (2)	O7—C24—C17	119.4 (2)
C25—N1—Mn2	124.95 (18)	O8—C24—C17	116.1 (2)
C29—N1—Mn2	116.78 (15)	N1—C25—C26	123.1 (3)
C36—N2—C33	118.2 (2)	N1—C25—H25	118.5
C36—N2—Mn2	124.99 (16)	C26—C25—H25	118.5
C33—N2—Mn2	116.75 (15)	C27—C26—C25	118.2 (3)
O1—C1—O2	126.5 (2)	C27—C26—H26	120.9
O1—C1—C2	115.88 (18)	C25—C26—H26	120.9
O2—C1—C2	117.64 (19)	C26—C27—C28	120.2 (3)
C3—C2—C7	120.04 (19)	C26—C27—H27	119.9
C3—C2—C1	119.28 (19)	C28—C27—H27	119.9
C7—C2—C1	120.53 (19)	C27—C28—C29	118.1 (3)
C2—C3—C4	120.4 (2)	C27—C28—C30	121.3 (3)
C2—C3—H3	119.8	C29—C28—C30	120.6 (3)
C4—C3—H3	119.8	N1—C29—C28	122.1 (2)
C5—C4—C3	121.3 (2)	N1—C29—C33	116.7 (2)
C5—C4—H4	119.3	C28—C29—C33	121.2 (2)
C3—C4—H4	119.3	O9—C30—C28	122.4 (4)
C4—C5—C6	119.96 (19)	O9—C30—C31	119.5 (3)
C4—C5—C12	118.68 (19)	C28—C30—C31	118.1 (3)
C6—C5—C12	121.32 (19)	O10—C31—C32	121.4 (3)
C7—C6—C11	118.5 (2)	O10—C31—C30	119.5 (3)
C7—C6—C5	118.63 (19)	C32—C31—C30	119.1 (3)
C11—C6—C5	122.7 (2)	C34—C32—C33	118.5 (3)
C6—C7—C2	119.54 (19)	C34—C32—C31	121.8 (3)
C6—C7—C8	118.6 (2)	C33—C32—C31	119.7 (3)
C2—C7—C8	121.8 (2)	N2—C33—C32	121.8 (2)
C9—C8—C7	121.2 (2)	N2—C33—C29	117.1 (2)
C9—C8—H8	119.4	C32—C33—C29	121.1 (2)
C7—C8—H8	119.4	C35—C34—C32	119.9 (2)
C8—C9—C10	120.1 (2)	C35—C34—H34	120.0
C8—C9—H9	120.0	C32—C34—H34	120.0
C10—C9—H9	120.0	C34—C35—C36	118.2 (3)
C11—C10—C9	120.9 (2)	C34—C35—H35	120.9
C11—C10—H10	119.6	C36—C35—H35	120.9
C9—C10—H10	119.6	N2—C36—C35	123.3 (3)
C10—C11—C6	120.7 (2)	N2—C36—H36	118.3
C10—C11—H11	119.7	C35—C36—H36	118.3
C6—C11—H11	119.7

O1w—Mn1—O1—C1	−164.4 (2)	Mn1—O5—C13—O6	−0.3 (3)
O7ⁱⁱ—Mn1—O1—C1	−66.9 (2)	Mn2—O5—C13—O6	129.4 (2)
O5—Mn1—O1—C1	46.0 (2)	Mn1—O5—C13—C14	176.44 (16)
O8ⁱⁱ—Mn2—O2—C1	51.2 (3)	Mn2—O5—C13—C14	−53.8 (3)
O3ⁱⁱⁱ—Mn2—O2—C1	146.4 (2)	O6—C13—C14—C15	111.3 (3)
O5—Mn2—O2—C1	−31.5 (2)	O5—C13—C14—C15	−65.5 (3)
N2—Mn2—O2—C1	−101.3 (3)	O6—C13—C14—C19	−70.4 (3)
N1—Mn2—O2—C1	−127.8 (2)	O5—C13—C14—C19	112.9 (2)
O1—Mn1—O5—C13	86.84 (14)	C19—C14—C15—C16	3.0 (4)
O4ⁱ—Mn1—O5—C13	−94.63 (14)	C13—C14—C15—C16	−178.6 (2)
O1w—Mn1—O5—C13	−12.3 (2)	C14—C15—C16—C17	−2.5 (4)
O7ⁱⁱ—Mn1—O5—C13	178.04 (13)	C15—C16—C17—C18	−0.7 (3)
O1—Mn1—O5—Mn2	−62.92 (7)	C15—C16—C17—C24	174.5 (2)
O4ⁱ—Mn1—O5—Mn2	115.60 (7)	C16—C17—C18—C23	−175.0 (2)
O1w—Mn1—O5—Mn2	−162.08 (11)	C24—C17—C18—C23	9.8 (3)
O7ⁱⁱ—Mn1—O5—Mn2	28.27 (10)	C16—C17—C18—C19	3.3 (3)
O8ⁱⁱ—Mn2—O5—C13	−172.7 (2)	C24—C17—C18—C19	−171.9 (2)
O2—Mn2—O5—C13	−71.3 (2)	C15—C14—C19—C20	177.4 (2)
N2—Mn2—O5—C13	94.0 (2)	C13—C14—C19—C20	−0.9 (3)
N1—Mn2—O5—C13	22.2 (2)	C15—C14—C19—C18	−0.3 (3)
O8ⁱⁱ—Mn2—O5—Mn1	−44.29 (8)	C13—C14—C19—C18	−178.62 (19)
O2—Mn2—O5—Mn1	57.10 (8)	C17—C18—C19—C20	179.5 (2)
N2—Mn2—O5—Mn1	−137.63 (8)	C23—C18—C19—C20	−2.2 (3)
N1—Mn2—O5—Mn1	150.64 (7)	C17—C18—C19—C14	−2.8 (3)
O8ⁱⁱ—Mn2—N1—C25	176.3 (3)	C23—C18—C19—C14	175.6 (2)
O2—Mn2—N1—C25	−7.4 (2)	C14—C19—C20—C21	−177.6 (2)
O3ⁱⁱⁱ—Mn2—N1—C25	80.76 (19)	C18—C19—C20—C21	0.0 (3)
O5—Mn2—N1—C25	−98.1 (2)	C19—C20—C21—C22	2.0 (4)
N2—Mn2—N1—C25	179.9 (2)	C20—C21—C22—C23	−1.9 (4)
O8ⁱⁱ—Mn2—N1—C29	−0.9 (4)	C21—C22—C23—C18	−0.3 (4)
O2—Mn2—N1—C29	175.46 (16)	C17—C18—C23—C22	−179.4 (2)
O3ⁱⁱⁱ—Mn2—N1—C29	−96.40 (16)	C19—C18—C23—C22	2.3 (3)
O5—Mn2—N1—C29	84.77 (16)	Mn1^vi—O7—C24—O8	−18.2 (3)
N2—Mn2—N1—C29	2.70 (15)	Mn1^vi—O7—C24—C17	161.82 (17)
O8ⁱⁱ—Mn2—N2—C36	−4.72 (19)	Mn2^vi—O8—C24—O7	−45.2 (4)
O2—Mn2—N2—C36	148.4 (2)	Mn2^vi—O8—C24—C17	134.8 (2)
O3ⁱⁱⁱ—Mn2—N2—C36	−100.44 (18)	C16—C17—C24—O7	64.1 (3)
O5—Mn2—N2—C36	77.79 (18)	C18—C17—C24—O7	−120.7 (3)
N1—Mn2—N2—C36	176.2 (2)	C16—C17—C24—O8	−115.9 (3)
O8ⁱⁱ—Mn2—N2—C33	177.08 (15)	C18—C17—C24—O8	59.3 (3)
O2—Mn2—N2—C33	−29.8 (3)	C29—N1—C25—C26	−0.8 (4)
O3ⁱⁱⁱ—Mn2—N2—C33	81.36 (15)	Mn2—N1—C25—C26	−177.9 (2)
O5—Mn2—N2—C33	−100.41 (15)	N1—C25—C26—C27	0.9 (4)
N1—Mn2—N2—C33	−1.99 (14)	C25—C26—C27—C28	0.1 (5)
Mn1—O1—C1—O2	−16.1 (4)	C26—C27—C28—C29	−1.2 (4)
Mn1—O1—C1—C2	163.06 (14)	C26—C27—C28—C30	178.7 (3)
Mn2—O2—C1—O1	7.0 (4)	C25—N1—C29—C28	−0.4 (3)
Mn2—O2—C1—C2	−172.07 (16)	Mn2—N1—C29—C28	177.00 (17)
O1—C1—C2—C3	56.6 (3)	C25—N1—C29—C33	179.6 (2)
O2—C1—C2—C3	−124.2 (2)	Mn2—N1—C29—C33	−3.1 (2)
O1—C1—C2—C7	−118.8 (2)	C27—C28—C29—N1	1.3 (4)
O2—C1—C2—C7	60.4 (3)	C30—C28—C29—N1	−178.5 (2)
C7—C2—C3—C4	−1.2 (3)	C27—C28—C29—C33	−178.6 (2)
C1—C2—C3—C4	−176.65 (19)	C30—C28—C29—C33	1.6 (4)
C2—C3—C4—C5	−1.8 (3)	C27—C28—C30—O9	−6.6 (5)
C3—C4—C5—C6	2.5 (3)	C29—C28—C30—O9	173.2 (3)
C3—C4—C5—C12	−179.48 (19)	C27—C28—C30—C31	174.9 (3)
C4—C5—C6—C7	−0.3 (3)	C29—C28—C30—C31	−5.2 (4)
C12—C5—C6—C7	−178.25 (19)	O9—C30—C31—O10	5.6 (5)
C4—C5—C6—C11	175.6 (2)	C28—C30—C31—O10	−175.9 (3)
C12—C5—C6—C11	−2.4 (3)	O9—C30—C31—C32	−173.1 (3)
C11—C6—C7—C2	−178.6 (2)	C28—C30—C31—C32	5.4 (4)
C5—C6—C7—C2	−2.6 (3)	O10—C31—C32—C34	−1.0 (4)
C11—C6—C7—C8	−2.4 (3)	C30—C31—C32—C34	177.7 (3)
C5—C6—C7—C8	173.62 (19)	O10—C31—C32—C33	179.5 (3)
C3—C2—C7—C6	3.4 (3)	C30—C31—C32—C33	−1.9 (4)
C1—C2—C7—C6	178.75 (19)	C36—N2—C33—C32	1.9 (3)
C3—C2—C7—C8	−172.7 (2)	Mn2—N2—C33—C32	−179.80 (17)
C1—C2—C7—C8	2.6 (3)	C36—N2—C33—C29	−177.2 (2)
C6—C7—C8—C9	0.7 (3)	Mn2—N2—C33—C29	1.2 (2)
C2—C7—C8—C9	176.8 (2)	C34—C32—C33—N2	−0.5 (3)
C7—C8—C9—C10	1.3 (4)	C31—C32—C33—N2	179.1 (2)
C8—C9—C10—C11	−1.6 (4)	C34—C32—C33—C29	178.5 (2)
C9—C10—C11—C6	−0.1 (4)	C31—C32—C33—C29	−1.9 (3)
C7—C6—C11—C10	2.2 (4)	N1—C29—C33—N2	1.3 (3)
C5—C6—C11—C10	−173.7 (2)	C28—C29—C33—N2	−178.8 (2)
Mn1^v—O4—C12—O3	2.2 (4)	N1—C29—C33—C32	−177.8 (2)
Mn1^v—O4—C12—C5	−175.79 (15)	C28—C29—C33—C32	2.2 (3)
Mn2^iv—O3—C12—O4	139.82 (19)	C33—C32—C34—C35	−1.4 (4)
Mn2^iv—O3—C12—C5	−42.2 (3)	C31—C32—C34—C35	179.0 (2)
C4—C5—C12—O4	130.1 (2)	C32—C34—C35—C36	1.8 (4)
C6—C5—C12—O4	−51.9 (3)	C33—N2—C36—C35	−1.4 (3)
C4—C5—C12—O3	−48.0 (3)	Mn2—N2—C36—C35	−179.60 (18)
C6—C5—C12—O3	130.0 (2)	C34—C35—C36—N2	−0.4 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O3ⁱ	0.85 (1)	1.93 (2)	2.720 (2)	155 (3)

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

Experimental details

Crystal data
Chemical formula	[Mn₂(C₁₂H₆O₄)₂(C₁₂H₆N₂O₂)(H₂O)]
M_r	766.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.4393 (8), 19.2477 (18), 19.2504 (19)
β (°)	101.781 (1)
V (Å³)	3061.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.90
Crystal size (mm)	0.27 × 0.26 × 0.20

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.794, 0.841
No. of measured, independent and observed [I > 2σ(I)] reflections	16986, 6015, 4853
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.096, 1.03
No. of reflections	6015
No. of parameters	466
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)	0.40, −0.24

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Selected bond lengths (Å) top

Mn1—O1	2.106 (2)	Mn2—O2	2.125 (2)
Mn1—O4ⁱ	2.137 (2)	Mn2—O3ⁱⁱⁱ	2.173 (2)
Mn1—O5	2.190 (2)	Mn2—O5	2.192 (2)
Mn1—O6	2.545 (2)	Mn2—O8ⁱⁱ	2.104 (2)
Mn1—O7ⁱⁱ	2.182 (2)	Mn2—N1	2.273 (2)
Mn1—O1W	2.157 (2)	Mn2—N2	2.268 (2)

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

Acknowledgements

The authors thank Tianjin Agricultural University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Boeckmann, J., Jess, I. & Näther, C. (2009). Acta Cryst. E65, m421. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, H.-D., Li, X.-Y., Xu, M.-L. & Ng, S. W. (2008). Acta Cryst. E64, m701–m702. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.