catena-Poly[[diaqua­(1,10-phenanthroline-κ²N,N′)manganese(II)]-μ-acetyl­enedicarboxylato-κ²O:O′]

In the title complex, [Mn(C₄O₄)(C₁₂H₈N₂)(H₂O)₂]_n, each Mn^II ion is octa­hedrally coordinated by two N atoms of a 1,10-phenanthroline ligand, two carboxylate O atoms of different acetyl­enedicarboxyl­ate (ace²⁻) ligands and two coordinated water mol­ecules, and the octa­hedral units are connected by ace²⁻ bridges, which adopt a bis-monodentate coordination mode, to form a one-dimensional structure along the [101] direction. A three-dimensional supra­molecular architecture is constructed via hydrogen-bond and π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.026
• wR factor = 0.075
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C13    -   C14    ...       1.48 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C15    -   C16    ...       1.47 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

catena-Poly[[diaqua(1,10-phenanthroline-κ²N,N')manganese(II)]- µ-acetylenedicarboxylato-κ²O:O']

Crystal data

[Mn(C4O4)(C12H8N2)(H2O)2]	F(000) = 780
Mr = 383.22	Dx = 1.584 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 13325 reflections
a = 13.764 (3) Å	θ = 3.0–27.5°
b = 8.2793 (17) Å	µ = 0.86 mm^−1
c = 14.218 (3) Å	T = 295 K
β = 97.24 (3)°	Block, yellow
V = 1607.3 (6) Å^3	0.35 × 0.32 × 0.25 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID area-detector diffractometer	3668 independent reflections
Radiation source: fine-focus sealed tube	3285 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 10 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −17→17
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −10→10
Tmin = 0.753, Tmax = 0.814	l = −18→18
15165 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0406P)^2 + 0.3898P] where P = (Fo^2 + 2Fc^2)/3
3668 reflections	(Δ/σ)max = 0.001
238 parameters	Δρmax = 0.29 e Å^−3
6 restraints	Δρmin = −0.17 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Mn1	0.263824 (14)	0.19217 (3)	0.478011 (13)	0.02743 (8)
O1W	0.34457 (9)	0.24466 (19)	0.36181 (8)	0.0492 (3)
H1W1	0.4041 (8)	0.254 (3)	0.3828 (14)	0.074*
H1W2	0.3295 (15)	0.302 (2)	0.3130 (11)	0.074*
O2W	0.30580 (8)	−0.06403 (13)	0.47381 (8)	0.0382 (2)
H2W1	0.3609 (9)	−0.110 (2)	0.4904 (12)	0.057*
H2W2	0.2856 (13)	−0.090 (2)	0.4167 (8)	0.057*
O1	0.14362 (8)	0.13848 (14)	0.36912 (7)	0.0401 (3)
O2	0.19570 (9)	−0.07524 (15)	0.29402 (8)	0.0493 (3)
O3	−0.10838 (8)	0.22562 (15)	0.06850 (7)	0.0429 (3)
O4	0.01697 (8)	0.27150 (17)	−0.01381 (8)	0.0483 (3)
N1	0.19095 (8)	0.15287 (15)	0.60976 (8)	0.0295 (2)
N2	0.18131 (8)	0.42439 (14)	0.50162 (8)	0.0324 (3)
C1	0.19612 (11)	0.02023 (19)	0.66274 (11)	0.0373 (3)
H1	0.2270	−0.0702	0.6415	0.045*
C2	0.15724 (12)	0.0101 (2)	0.74907 (12)	0.0465 (4)
H2	0.1624	−0.0851	0.7841	0.056*
C3	0.11171 (13)	0.1418 (2)	0.78090 (11)	0.0470 (4)
H3	0.0866	0.1376	0.8386	0.056*
C4	0.10281 (12)	0.2839 (2)	0.72633 (11)	0.0394 (3)
C5	0.05317 (14)	0.4258 (2)	0.75328 (13)	0.0529 (4)
H5	0.0274	0.4275	0.8107	0.063*
C6	0.04345 (14)	0.5561 (2)	0.69670 (14)	0.0538 (5)
H6	0.0092	0.6454	0.7148	0.065*
C7	0.08452 (11)	0.56086 (18)	0.60907 (12)	0.0402 (3)
C8	0.07432 (13)	0.69356 (19)	0.54716 (15)	0.0489 (4)
H8	0.0386	0.7836	0.5616	0.059*
C9	0.11688 (13)	0.6898 (2)	0.46592 (15)	0.0504 (4)
H9	0.1102	0.7767	0.4241	0.061*
C10	0.17098 (12)	0.5535 (2)	0.44592 (12)	0.0434 (4)
H10	0.2011	0.5535	0.3909	0.052*
C11	0.13742 (10)	0.42660 (17)	0.58191 (10)	0.0307 (3)
C12	0.14421 (10)	0.28380 (17)	0.64053 (10)	0.0299 (3)
C13	0.14989 (10)	0.05387 (18)	0.29721 (10)	0.0328 (3)
C14	0.09524 (10)	0.11420 (19)	0.20821 (10)	0.0344 (3)
C15	0.04650 (10)	0.16367 (19)	0.13887 (10)	0.0339 (3)
C16	−0.01960 (10)	0.22563 (18)	0.05726 (9)	0.0316 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.02442 (12)	0.03663 (13)	0.02093 (11)	0.00054 (8)	0.00167 (8)	−0.00220 (8)
O1W	0.0361 (6)	0.0798 (8)	0.0311 (6)	−0.0078 (6)	0.0023 (5)	0.0177 (6)
O2W	0.0358 (6)	0.0410 (6)	0.0359 (5)	0.0086 (4)	−0.0029 (4)	−0.0032 (5)
O1	0.0333 (5)	0.0549 (6)	0.0296 (5)	0.0098 (5)	−0.0059 (4)	−0.0116 (5)
O2	0.0588 (7)	0.0511 (7)	0.0329 (5)	0.0208 (6)	−0.0135 (5)	−0.0102 (5)
O3	0.0270 (5)	0.0702 (8)	0.0309 (5)	0.0060 (5)	0.0019 (4)	0.0151 (5)
O4	0.0325 (6)	0.0827 (9)	0.0293 (5)	−0.0096 (6)	0.0017 (4)	0.0108 (6)
N1	0.0263 (5)	0.0357 (6)	0.0262 (5)	−0.0004 (5)	0.0022 (4)	−0.0003 (5)
N2	0.0293 (6)	0.0349 (6)	0.0329 (6)	−0.0031 (5)	0.0032 (5)	0.0010 (5)
C1	0.0348 (7)	0.0406 (8)	0.0359 (7)	0.0000 (6)	0.0023 (6)	0.0060 (6)
C2	0.0425 (9)	0.0585 (10)	0.0385 (8)	−0.0055 (8)	0.0049 (7)	0.0160 (8)
C3	0.0434 (9)	0.0696 (11)	0.0298 (7)	−0.0086 (8)	0.0117 (6)	0.0042 (8)
C4	0.0347 (7)	0.0536 (9)	0.0314 (7)	−0.0055 (7)	0.0091 (6)	−0.0060 (7)
C5	0.0519 (10)	0.0665 (11)	0.0445 (9)	−0.0006 (9)	0.0226 (8)	−0.0171 (9)
C6	0.0505 (10)	0.0534 (10)	0.0603 (11)	0.0047 (8)	0.0180 (9)	−0.0236 (9)
C7	0.0336 (7)	0.0366 (8)	0.0501 (9)	−0.0015 (6)	0.0041 (7)	−0.0124 (7)
C8	0.0411 (9)	0.0321 (8)	0.0718 (12)	0.0009 (6)	0.0001 (8)	−0.0073 (8)
C9	0.0448 (9)	0.0362 (8)	0.0682 (12)	−0.0032 (7)	−0.0015 (9)	0.0116 (8)
C10	0.0401 (8)	0.0439 (8)	0.0462 (9)	−0.0041 (7)	0.0058 (7)	0.0095 (7)
C11	0.0250 (6)	0.0343 (7)	0.0324 (7)	−0.0035 (5)	0.0022 (5)	−0.0061 (6)
C12	0.0247 (6)	0.0382 (7)	0.0268 (6)	−0.0036 (5)	0.0036 (5)	−0.0056 (6)
C13	0.0267 (6)	0.0431 (8)	0.0269 (6)	0.0024 (6)	−0.0037 (5)	−0.0036 (6)
C14	0.0302 (7)	0.0425 (8)	0.0294 (7)	0.0046 (6)	−0.0011 (6)	−0.0058 (6)
C15	0.0266 (6)	0.0457 (8)	0.0290 (7)	0.0026 (6)	0.0017 (5)	−0.0011 (6)
C16	0.0273 (6)	0.0414 (7)	0.0249 (6)	−0.0005 (6)	−0.0010 (5)	−0.0002 (6)

Geometric parameters (Å, º)

Mn1—O1W	2.1485 (13)	C2—C3	1.363 (3)
Mn1—O3^i	2.1545 (12)	C2—H2	0.9300
Mn1—O1	2.1647 (12)	C3—C4	1.406 (3)
Mn1—O2W	2.2013 (12)	C3—H3	0.9300
Mn1—N1	2.2571 (13)	C4—C12	1.410 (2)
Mn1—N2	2.2792 (13)	C4—C5	1.435 (2)
O1W—H1W1	0.839 (9)	C5—C6	1.342 (3)
O1W—H1W2	0.845 (9)	C5—H5	0.9300
O2W—H2W1	0.853 (9)	C6—C7	1.432 (3)
O2W—H2W2	0.851 (9)	C6—H6	0.9300
O1—C13	1.2513 (17)	C7—C8	1.404 (3)
O2—C13	1.2448 (18)	C7—C11	1.409 (2)
O3—C16	1.2522 (17)	C8—C9	1.360 (3)
O3—Mn1^ii	2.1545 (12)	C8—H8	0.9300
O4—C16	1.2437 (18)	C9—C10	1.401 (2)
N1—C1	1.3285 (19)	C9—H9	0.9300
N1—C12	1.3606 (18)	C10—H10	0.9300
N2—C10	1.327 (2)	C11—C12	1.443 (2)
N2—C11	1.3573 (18)	C13—C14	1.4754 (19)
C1—C2	1.402 (2)	C14—C15	1.193 (2)
C1—H1	0.9300	C15—C16	1.4735 (19)
O1W—Mn1—O3^i	86.15 (5)	C4—C3—H3	120.1
O1W—Mn1—O1	85.09 (5)	C3—C4—C12	117.43 (15)
O3^i—Mn1—O1	170.00 (5)	C3—C4—C5	123.29 (15)
O1W—Mn1—O2W	90.63 (5)	C12—C4—C5	119.28 (15)
O3^i—Mn1—O2W	97.08 (5)	C6—C5—C4	120.85 (15)
O1—Mn1—O2W	87.84 (4)	C6—C5—H5	119.6
O1W—Mn1—N1	173.91 (5)	C4—C5—H5	119.6
O3^i—Mn1—N1	87.98 (4)	C5—C6—C7	121.54 (15)
O1—Mn1—N1	100.62 (5)	C5—C6—H6	119.2
O2W—Mn1—N1	91.67 (4)	C7—C6—H6	119.2
O1W—Mn1—N2	104.97 (5)	C8—C7—C11	117.39 (15)
O3^i—Mn1—N2	91.72 (5)	C8—C7—C6	123.22 (16)
O1—Mn1—N2	85.89 (4)	C11—C7—C6	119.40 (15)
O2W—Mn1—N2	162.59 (4)	C9—C8—C7	119.68 (15)
N1—Mn1—N2	73.60 (5)	C9—C8—H8	120.2
Mn1—O1W—H1W1	108.8 (15)	C7—C8—H8	120.2
Mn1—O1W—H1W2	130.4 (16)	C8—C9—C10	119.18 (16)
H1W1—O1W—H1W2	111.5 (15)	C8—C9—H9	120.4
Mn1—O2W—H2W1	130.2 (14)	C10—C9—H9	120.4
Mn1—O2W—H2W2	102.2 (13)	N2—C10—C9	123.20 (16)
H2W1—O2W—H2W2	109.0 (13)	N2—C10—H10	118.4
C13—O1—Mn1	125.04 (9)	C9—C10—H10	118.4
C16—O3—Mn1^ii	131.31 (9)	N2—C11—C7	122.76 (14)
C1—N1—C12	118.03 (13)	N2—C11—C12	118.13 (12)
C1—N1—Mn1	126.31 (10)	C7—C11—C12	119.10 (13)
C12—N1—Mn1	115.44 (9)	N1—C12—C4	122.51 (14)
C10—N2—C11	117.73 (13)	N1—C12—C11	117.78 (12)
C10—N2—Mn1	127.55 (11)	C4—C12—C11	119.72 (13)
C11—N2—Mn1	114.71 (9)	O2—C13—O1	126.73 (13)
N1—C1—C2	123.15 (15)	O2—C13—C14	117.72 (13)
N1—C1—H1	118.4	O1—C13—C14	115.54 (13)
C2—C1—H1	118.4	C15—C14—C13	176.29 (16)
C3—C2—C1	119.01 (16)	C14—C15—C16	175.91 (16)
C3—C2—H2	120.5	O4—C16—O3	127.23 (13)
C1—C2—H2	120.5	O4—C16—C15	118.25 (13)
C2—C3—C4	119.85 (15)	O3—C16—C15	114.52 (13)
C2—C3—H3	120.1
O1W—Mn1—O1—C13	46.50 (13)	C5—C6—C7—C8	178.73 (17)
O3^i—Mn1—O1—C13	75.4 (3)	C5—C6—C7—C11	−0.8 (3)
O2W—Mn1—O1—C13	−44.32 (13)	C11—C7—C8—C9	−1.5 (2)
N1—Mn1—O1—C13	−135.62 (13)	C6—C7—C8—C9	178.94 (17)
N2—Mn1—O1—C13	151.93 (13)	C7—C8—C9—C10	−0.5 (3)
O3^i—Mn1—N1—C1	−87.30 (12)	C11—N2—C10—C9	−0.4 (2)
O1—Mn1—N1—C1	97.85 (12)	Mn1—N2—C10—C9	178.70 (12)
O2W—Mn1—N1—C1	9.73 (12)	C8—C9—C10—N2	1.6 (3)
N2—Mn1—N1—C1	−179.69 (12)	C10—N2—C11—C7	−1.8 (2)
O3^i—Mn1—N1—C12	87.14 (10)	Mn1—N2—C11—C7	178.93 (11)
O1—Mn1—N1—C12	−87.72 (10)	C10—N2—C11—C12	177.03 (13)
O2W—Mn1—N1—C12	−175.83 (9)	Mn1—N2—C11—C12	−2.19 (15)
N2—Mn1—N1—C12	−5.26 (9)	C8—C7—C11—N2	2.8 (2)
O1W—Mn1—N2—C10	10.89 (13)	C6—C7—C11—N2	−177.65 (14)
O3^i—Mn1—N2—C10	97.36 (13)	C8—C7—C11—C12	−176.04 (13)
O1—Mn1—N2—C10	−72.91 (13)	C6—C7—C11—C12	3.5 (2)
O2W—Mn1—N2—C10	−142.10 (15)	C1—N1—C12—C4	0.9 (2)
N1—Mn1—N2—C10	−175.25 (13)	Mn1—N1—C12—C4	−174.06 (11)
O1W—Mn1—N2—C11	−169.98 (9)	C1—N1—C12—C11	−179.00 (12)
O3^i—Mn1—N2—C11	−83.51 (10)	Mn1—N1—C12—C11	6.08 (15)
O1—Mn1—N2—C11	106.22 (10)	C3—C4—C12—N1	0.3 (2)
O2W—Mn1—N2—C11	37.03 (19)	C5—C4—C12—N1	−178.94 (14)
N1—Mn1—N2—C11	3.88 (9)	C3—C4—C12—C11	−179.83 (13)
C12—N1—C1—C2	−1.1 (2)	C5—C4—C12—C11	0.9 (2)
Mn1—N1—C1—C2	173.24 (11)	N2—C11—C12—N1	−2.60 (18)
N1—C1—C2—C3	0.1 (2)	C7—C11—C12—N1	176.31 (12)
C1—C2—C3—C4	1.2 (2)	N2—C11—C12—C4	177.54 (12)
C2—C3—C4—C12	−1.3 (2)	C7—C11—C12—C4	−3.5 (2)
C2—C3—C4—C5	177.89 (17)	Mn1—O1—C13—O2	42.2 (2)
C3—C4—C5—C6	−177.35 (17)	Mn1—O1—C13—C14	−138.99 (11)
C12—C4—C5—C6	1.9 (3)	Mn1^ii—O3—C16—O4	−2.3 (3)
C4—C5—C6—C7	−1.9 (3)	Mn1^ii—O3—C16—C15	177.63 (10)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O4^i	0.84 (1)	2.01 (1)	2.7781 (18)	152 (2)
O1W—H1W2···O2^iii	0.85 (1)	1.83 (1)	2.6701 (17)	177 (2)
O2W—H2W1···O4^iv	0.85 (1)	1.94 (1)	2.7890 (16)	173 (2)
O2W—H2W2···O2	0.85 (1)	2.01 (1)	2.8042 (17)	155 (2)

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