Diaqua­bis[(E)-2-(4-oxopentan-2-ylideneamino)­benzoato-κO]dipyridine­manganese(II)

The Mn atom in the title compound, [Mn(C₁₂H₁₃NO₂)₂(C₅H₅N)₂(H₂O)₂], is coordinated by two pyridine heterocycles, two water mol­ecules and an O-atom donor in two substituted benzoate groups, in an all-trans arrangement with the Mn atom on a center of inversion. The benzoate mean plane is inclined to the coordination plane formed by the four O atoms, with a dihedral angle of 43.4 (1)°. The dihedral angle between the planes of the benzene ring and the Schiff base is 49.5 (1)°.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.116
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.86
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Mn1    -   O4      ..       5.31 su

   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: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Diaquabis[(E)-2-(4-oxopentan-2-ylideneamino)benzoato-κO]dipyridinemanganese(II)

Crystal data

[Mn(C12H13NO2)2(C5H5N)2(H2O)2]	F(000) = 714
Mr = 683.61	Dx = 1.333 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 3130 reflections
a = 9.9611 (7) Å	θ = 2.6–24.0°
b = 14.5346 (10) Å	µ = 0.44 mm^−1
c = 12.5321 (8) Å	T = 292 K
β = 110.109 (1)°	Block, colorless
V = 1703.8 (2) Å^3	0.24 × 0.20 × 0.15 mm
Z = 2

Data collection

Bruker SMART Apex CCD area-detector diffractometer	3871 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	2776 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
0.3° wide ω exposures scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −12→12
Tmin = 0.901, Tmax = 0.957	k = −15→18
10543 measured reflections	l = −9→16

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0611P)^2] where P = (Fo^2 + 2Fc^2)/3
3871 reflections	(Δ/σ)max = 0.001
222 parameters	Δρmax = 0.55 e Å^−3
3 restraints	Δρmin = −0.19 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	0.5000	0.0000	0.0000	0.04248 (15)
N1	0.26069 (17)	0.18638 (10)	0.14822 (13)	0.0506 (4)
N2	0.27531 (16)	0.04194 (12)	−0.12028 (13)	0.0505 (4)
O1	0.39905 (17)	0.25445 (10)	0.01491 (12)	0.0647 (4)
O2	0.38598 (19)	−0.08348 (10)	0.20958 (14)	0.0763 (5)
O3	0.43942 (14)	0.04670 (9)	0.14000 (11)	0.0494 (3)
O4	0.58958 (16)	0.13585 (9)	−0.01297 (13)	0.0594 (4)
H4A	0.603 (3)	0.1317 (17)	−0.0734 (13)	0.089*
H4B	0.541 (2)	0.1797 (13)	−0.0070 (18)	0.089*
C1	0.32937 (18)	0.05552 (12)	0.27923 (15)	0.0422 (4)
C2	0.3325 (2)	0.01531 (14)	0.38137 (17)	0.0518 (5)
H2	0.3745	−0.0422	0.4014	0.062*
C3	0.2748 (2)	0.05919 (16)	0.45282 (18)	0.0644 (6)
H3	0.2769	0.0312	0.5201	0.077*
C4	0.2142 (2)	0.14427 (17)	0.4244 (2)	0.0672 (6)
H4	0.1744	0.1738	0.4723	0.081*
C5	0.2117 (2)	0.18634 (15)	0.32581 (18)	0.0604 (6)
H5	0.1730	0.2450	0.3087	0.072*
C6	0.26612 (19)	0.14257 (13)	0.25153 (16)	0.0463 (4)
C7	0.0037 (3)	0.22528 (19)	0.0918 (2)	0.0826 (7)
H7A	−0.0017	0.1688	0.1298	0.124*
H7B	−0.0715	0.2269	0.0192	0.124*
H7C	−0.0066	0.2763	0.1370	0.124*
C8	0.1466 (2)	0.23123 (14)	0.07534 (18)	0.0569 (5)
C9	0.1574 (3)	0.27846 (15)	−0.01606 (18)	0.0648 (6)
H9	0.0746	0.3060	−0.0644	0.078*
C10	0.2825 (3)	0.28914 (14)	−0.04355 (18)	0.0632 (6)
C11	0.2761 (4)	0.34477 (19)	−0.1470 (2)	0.0949 (9)
H11A	0.3433	0.3946	−0.1245	0.142*
H11B	0.1815	0.3690	−0.1820	0.142*
H11C	0.2996	0.3061	−0.2001	0.142*
C12	0.3896 (2)	0.00206 (12)	0.20425 (16)	0.0451 (4)
C13	0.1608 (2)	0.02210 (17)	−0.0933 (2)	0.0685 (6)
H13	0.1735	−0.0116	−0.0275	0.082*
C14	0.0247 (2)	0.0488 (2)	−0.1576 (2)	0.0789 (7)
H14	−0.0526	0.0323	−0.1362	0.095*
C15	0.0046 (3)	0.09978 (19)	−0.2532 (2)	0.0790 (7)
H15	−0.0860	0.1200	−0.2974	0.095*
C16	0.1205 (3)	0.1201 (2)	−0.2821 (2)	0.0797 (7)
H16	0.1104	0.1542	−0.3472	0.096*
C17	0.2524 (2)	0.09011 (16)	−0.21433 (18)	0.0637 (6)
H17	0.3306	0.1044	−0.2357	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.0445 (2)	0.0353 (2)	0.0496 (3)	0.00001 (16)	0.01868 (18)	0.00406 (16)
N1	0.0591 (10)	0.0376 (9)	0.0486 (9)	0.0105 (7)	0.0101 (7)	0.0028 (7)
N2	0.0480 (9)	0.0511 (10)	0.0506 (10)	−0.0011 (8)	0.0147 (7)	0.0008 (8)
O1	0.0794 (11)	0.0504 (9)	0.0631 (9)	0.0105 (8)	0.0228 (8)	0.0006 (7)
O2	0.1223 (14)	0.0388 (8)	0.0941 (12)	0.0098 (8)	0.0706 (11)	0.0069 (8)
O3	0.0576 (8)	0.0401 (7)	0.0557 (8)	0.0018 (6)	0.0258 (6)	0.0026 (6)
O4	0.0714 (10)	0.0403 (8)	0.0745 (10)	−0.0042 (7)	0.0353 (8)	0.0010 (7)
C1	0.0375 (9)	0.0406 (10)	0.0455 (10)	−0.0013 (8)	0.0105 (8)	−0.0014 (8)
C2	0.0561 (12)	0.0480 (12)	0.0505 (12)	0.0000 (9)	0.0172 (10)	0.0019 (9)
C3	0.0772 (15)	0.0688 (16)	0.0533 (13)	−0.0052 (12)	0.0303 (11)	−0.0009 (11)
C4	0.0766 (16)	0.0645 (15)	0.0707 (15)	0.0023 (12)	0.0383 (12)	−0.0147 (12)
C5	0.0677 (14)	0.0507 (12)	0.0631 (13)	0.0075 (10)	0.0229 (11)	−0.0090 (10)
C6	0.0441 (10)	0.0396 (10)	0.0520 (11)	0.0009 (8)	0.0126 (8)	−0.0045 (8)
C7	0.0586 (14)	0.0799 (18)	0.0963 (18)	0.0128 (13)	0.0100 (12)	0.0080 (15)
C8	0.0578 (12)	0.0402 (11)	0.0619 (13)	0.0074 (9)	0.0065 (10)	−0.0034 (9)
C9	0.0709 (15)	0.0469 (12)	0.0607 (13)	0.0159 (11)	0.0022 (11)	0.0061 (10)
C10	0.0891 (17)	0.0359 (11)	0.0572 (13)	0.0109 (11)	0.0155 (12)	−0.0028 (9)
C11	0.135 (3)	0.0716 (18)	0.0770 (17)	0.0162 (17)	0.0350 (17)	0.0210 (14)
C12	0.0471 (10)	0.0394 (10)	0.0490 (11)	0.0046 (8)	0.0168 (9)	0.0031 (8)
C13	0.0554 (13)	0.0802 (17)	0.0648 (14)	−0.0129 (12)	0.0140 (11)	0.0087 (12)
C14	0.0445 (13)	0.100 (2)	0.0852 (18)	−0.0119 (13)	0.0135 (12)	0.0043 (16)
C15	0.0534 (14)	0.0840 (18)	0.0804 (17)	0.0071 (12)	−0.0017 (12)	0.0008 (14)
C16	0.0755 (17)	0.093 (2)	0.0610 (14)	0.0142 (15)	0.0113 (12)	0.0200 (13)
C17	0.0609 (13)	0.0716 (15)	0.0600 (13)	0.0086 (11)	0.0228 (11)	0.0103 (11)

Geometric parameters (Å, º)

Mn1—O3^i	2.1520 (13)	C4—H4	0.9300
Mn1—O3	2.1521 (13)	C5—C6	1.382 (3)
Mn1—O4	2.1957 (14)	C5—H5	0.9300
Mn1—O4^i	2.1958 (14)	C7—C8	1.510 (3)
Mn1—N2^i	2.3093 (15)	C7—H7A	0.9600
Mn1—N2	2.3093 (15)	C7—H7B	0.9600
N1—C8	1.355 (2)	C7—H7C	0.9600
N1—C6	1.427 (2)	C8—C9	1.371 (3)
N2—C17	1.322 (3)	C9—C10	1.411 (3)
N2—C13	1.328 (3)	C9—H9	0.9300
O1—C10	1.247 (3)	C10—C11	1.510 (3)
O2—C12	1.246 (2)	C11—H11A	0.9600
O3—C12	1.261 (2)	C11—H11B	0.9600
O4—H4A	0.82 (2)	C11—H11C	0.9600
O4—H4B	0.82 (2)	C13—C14	1.374 (3)
C1—C2	1.397 (3)	C13—H13	0.9300
C1—C6	1.403 (3)	C14—C15	1.364 (3)
C1—C12	1.495 (3)	C14—H14	0.9300
C2—C3	1.376 (3)	C15—C16	1.355 (3)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.368 (3)	C16—C17	1.368 (3)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.372 (3)	C17—H17	0.9300
O3^i—Mn1—O3	180	C1—C6—N1	120.04 (17)
O3^i—Mn1—O4	89.33 (5)	C8—C7—H7A	109.5
O3—Mn1—O4	90.67 (5)	C8—C7—H7B	109.5
O3^i—Mn1—O4^i	90.67 (5)	H7A—C7—H7B	109.5
O3—Mn1—O4^i	89.33 (5)	C8—C7—H7C	109.5
O4—Mn1—O4^i	180	H7A—C7—H7C	109.5
O3^i—Mn1—N2^i	88.19 (5)	H7B—C7—H7C	109.5
O3—Mn1—N2^i	91.81 (5)	N1—C8—C9	121.0 (2)
O4—Mn1—N2^i	87.61 (6)	N1—C8—C7	119.5 (2)
O4^i—Mn1—N2^i	92.39 (6)	C9—C8—C7	119.4 (2)
O3^i—Mn1—N2	91.81 (5)	C8—C9—C10	126.1 (2)
O3—Mn1—N2	88.19 (5)	C8—C9—H9	117.0
O4—Mn1—N2	92.39 (6)	C10—C9—H9	117.0
O4^i—Mn1—N2	87.61 (6)	O1—C10—C9	122.3 (2)
N2^i—Mn1—N2	180	O1—C10—C11	118.5 (2)
C8—N1—C6	125.98 (18)	C9—C10—C11	119.2 (2)
C17—N2—C13	116.24 (18)	C10—C11—H11A	109.5
C17—N2—Mn1	123.61 (14)	C10—C11—H11B	109.5
C13—N2—Mn1	120.05 (15)	H11A—C11—H11B	109.5
C12—O3—Mn1	129.83 (12)	C10—C11—H11C	109.5
Mn1—O4—H4A	101.7 (19)	H11A—C11—H11C	109.5
Mn1—O4—H4B	115.4 (19)	H11B—C11—H11C	109.5
H4A—O4—H4B	115.7 (16)	O2—C12—O3	124.91 (18)
C2—C1—C6	118.07 (18)	O2—C12—C1	117.37 (17)
C2—C1—C12	118.09 (17)	O3—C12—C1	117.71 (17)
C6—C1—C12	123.81 (17)	N2—C13—C14	123.4 (2)
C3—C2—C1	121.3 (2)	N2—C13—H13	118.3
C3—C2—H2	119.4	C14—C13—H13	118.3
C1—C2—H2	119.4	C15—C14—C13	119.1 (2)
C4—C3—C2	119.7 (2)	C15—C14—H14	120.5
C4—C3—H3	120.1	C13—C14—H14	120.5
C2—C3—H3	120.2	C16—C15—C14	118.2 (2)
C3—C4—C5	120.4 (2)	C16—C15—H15	120.9
C3—C4—H4	119.8	C14—C15—H15	120.9
C5—C4—H4	119.8	C15—C16—C17	119.3 (2)
C4—C5—C6	120.8 (2)	C15—C16—H16	120.4
C4—C5—H5	119.6	C17—C16—H16	120.4
C6—C5—H5	119.6	N2—C17—C16	123.9 (2)
C5—C6—C1	119.67 (19)	N2—C17—H17	118.1
C5—C6—N1	120.28 (18)	C16—C17—H17	118.1
O3^i—Mn1—N2—C17	−47.11 (17)	C8—N1—C6—C5	−44.8 (3)
O3—Mn1—N2—C17	132.89 (17)	C8—N1—C6—C1	136.45 (19)
O4—Mn1—N2—C17	42.30 (17)	C6—N1—C8—C9	173.67 (18)
O4^i—Mn1—N2—C17	−137.70 (17)	C6—N1—C8—C7	−9.3 (3)
O3^i—Mn1—N2—C13	136.69 (17)	N1—C8—C9—C10	−2.2 (3)
O3—Mn1—N2—C13	−43.31 (17)	C7—C8—C9—C10	−179.2 (2)
O4—Mn1—N2—C13	−133.91 (17)	C8—C9—C10—O1	0.6 (3)
O4^i—Mn1—N2—C13	46.10 (17)	C8—C9—C10—C11	−179.1 (2)
O4—Mn1—O3—C12	−172.63 (16)	Mn1—O3—C12—O2	11.9 (3)
O4^i—Mn1—O3—C12	7.37 (16)	Mn1—O3—C12—C1	−167.71 (11)
N2^i—Mn1—O3—C12	−85.00 (16)	C2—C1—C12—O2	28.2 (3)
N2—Mn1—O3—C12	95.00 (16)	C6—C1—C12—O2	−149.92 (19)
C6—C1—C2—C3	0.4 (3)	C2—C1—C12—O3	−152.22 (18)
C12—C1—C2—C3	−177.82 (18)	C6—C1—C12—O3	29.7 (3)
C1—C2—C3—C4	−0.7 (3)	C17—N2—C13—C14	0.2 (4)
C2—C3—C4—C5	−0.6 (3)	Mn1—N2—C13—C14	176.6 (2)
C3—C4—C5—C6	2.1 (3)	N2—C13—C14—C15	−1.3 (4)
C4—C5—C6—C1	−2.4 (3)	C13—C14—C15—C16	1.5 (4)
C4—C5—C6—N1	178.88 (19)	C14—C15—C16—C17	−0.8 (4)
C2—C1—C6—C5	1.1 (3)	C13—N2—C17—C16	0.7 (3)
C12—C1—C6—C5	179.22 (17)	Mn1—N2—C17—C16	−175.68 (19)
C2—C1—C6—N1	179.87 (16)	C15—C16—C17—N2	−0.4 (4)
C12—C1—C6—N1	−2.0 (3)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O2^i	0.82 (2)	1.88 (1)	2.669 (2)	162 (3)
C16—H16···O1^ii	0.93	2.58	3.287 (3)	133
C5—H5···O2^iii	0.93	2.55	3.470 (3)	169
O4—H4B···O1	0.82 (2)	1.88 (1)	2.674 (2)	164 (3)

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