Bis(di-2-pyridylmethane­diol-κ³N,N′,O)manganese(II) bis­(acetate) tetra­hydrate

The Mn atom in the title compound, [Mn(C₁₁H₁₀N₂O₂)₂](CH₃CO₂)₂·4H₂O, which lies on a centre of inversion, displays a tetra­gonally distorted octa­hedral coordination. The compound is isostructural with the analogous copper complex [Reinoso, Vitoria, San Felices, Lezama & Gutiérrez-Zorrilla (2003). Acta Cryst. E59, m548–m550].

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.049
• wR factor = 0.173
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Mn1    -   O1      ..      16.86 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Mn1    -   N1      ..      14.27 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Mn1    -   N2      ..      14.56 su
PLAT731_ALERT_1_B Bond    Calc     0.85(5), Rep   0.852(10) ......       5.00 su-Ra
              O2W  -H2W2    1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.85(5), Rep   0.850(10) ......       5.00 su-Ra
              O2W  -H4#     1.555   1.555

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.51
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Mn1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C12
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT731_ALERT_1_C Bond    Calc     0.86(4), Rep   0.854(10) ......       4.00 su-Ra
              O1W  -H1W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(4), Rep   0.854(10) ......       4.00 su-Ra
              O1W  -H1W2    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(4), Rep   0.856(10) ......       4.00 su-Ra
              O2W  -H2W1    1.555   1.555
PLAT732_ALERT_1_C Angle   Calc      109(4), Rep   109.5(18) ......       2.22 su-Ra
              H1W1 -O1W  -H1W2    1.555   1.555   1.555
PLAT732_ALERT_1_C Angle   Calc      109(5), Rep   109.4(18) ......       2.78 su-Ra
              H2W1 -O2W  -H2W2    1.555   1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(4), Rep   0.850(10) ......       4.00 su-Ra
              O1W  -H1#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Ra
              O1W  -H2#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.860(10) ......       4.00 su-Ra
              O2W  -H3#     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.91(4), Rep   1.910(10) ......       4.00 su-Ra
              H2#  -O2W     1.555   1.555

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

  12 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: atomic coordinates taken from the isostructural Cu analog (Reinoso et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

Bis(di-2-pyridylmethanediol-κ³N,N',O)manganese(II) bis(acetate) tetrahydrate

Crystal data

[Mn(C11H10N2O2)2](C2H3O2)2·4H2O	F(000) = 678
Mr = 649.51	Dx = 1.383 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5397 reflections
a = 8.6266 (6) Å	θ = 2.4–27.2°
b = 7.8941 (5) Å	µ = 0.49 mm^−1
c = 23.137 (2) Å	T = 295 K
β = 98.018 (1)°	Irregular block, brown–red
V = 1560.2 (2) Å^3	0.38 × 0.32 × 0.23 mm
Z = 2

Data collection

Bruker APEXII area-detector diffractometer	3439 independent reflections
Radiation source: fine-focus sealed tube	2798 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 27.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.766, Tmax = 0.896	k = −10→10
13846 measured reflections	l = −29→29

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.173	w = 1/[σ^2(Fo^2) + (0.1162P)^2 + 0.3929P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
3439 reflections	Δρmax = 1.30 e Å^−3
222 parameters	Δρmin = −0.37 e Å^−3
8 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (3)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Mn1	0.5000	0.5000	0.5000	0.0330 (2)
O1	0.4613 (2)	0.7602 (2)	0.44555 (8)	0.0515 (5)
O2	0.2409 (3)	0.9346 (3)	0.43815 (10)	0.0645 (6)
O4	0.2284 (3)	0.9216 (4)	0.32511 (11)	0.0849 (8)
O3	0.4384 (3)	0.7593 (4)	0.33251 (9)	0.0751 (7)
O1W	0.7047 (4)	0.6288 (4)	0.29586 (15)	0.0949 (8)
O2W	0.9092 (4)	0.8919 (5)	0.28551 (15)	0.0965 (9)
N1	0.4193 (3)	0.6701 (3)	0.55412 (9)	0.0506 (5)
N2	0.2816 (3)	0.4824 (3)	0.45790 (11)	0.0493 (5)
C1	0.4467 (4)	0.6654 (4)	0.61231 (12)	0.0626 (7)
H1	0.5043	0.5761	0.6307	0.075*
C2	0.3911 (4)	0.7913 (5)	0.64600 (13)	0.0718 (9)
H2	0.4111	0.7869	0.6865	0.086*
C3	0.3058 (4)	0.9227 (5)	0.61842 (15)	0.0711 (9)
H3	0.2685	1.0085	0.6403	0.085*
C4	0.2755 (4)	0.9273 (4)	0.55817 (14)	0.0618 (7)
H4	0.2171	1.0147	0.5390	0.074*
C5	0.3349 (3)	0.7975 (3)	0.52725 (11)	0.0499 (6)
C6	0.2060 (4)	0.3359 (4)	0.44430 (13)	0.0614 (7)
H6	0.2560	0.2342	0.4553	0.074*
C7	0.0578 (4)	0.3324 (5)	0.41476 (16)	0.0740 (9)
H7	0.0074	0.2300	0.4053	0.089*
C8	−0.0148 (4)	0.4819 (5)	0.3995 (2)	0.0770 (11)
H8A	−0.1154	0.4818	0.3789	0.092*
C9	0.0587 (4)	0.6326 (5)	0.41410 (14)	0.0652 (8)
H9A	0.0080	0.7350	0.4048	0.078*
C10	0.2092 (3)	0.6294 (4)	0.44286 (11)	0.0489 (6)
C11	0.3104 (3)	0.7877 (3)	0.46102 (11)	0.0496 (6)
C12	0.3359 (4)	0.8474 (4)	0.30341 (13)	0.0663 (8)
C13	0.3406 (6)	0.8661 (7)	0.23881 (16)	0.1084 (15)
H13A	0.2628	0.9466	0.2228	0.163*
H13B	0.3197	0.7586	0.2200	0.163*
H13C	0.4423	0.9052	0.2325	0.163*
H1O	0.454 (4)	0.761 (5)	0.4077 (5)	0.076 (10)*
H2O	0.225 (5)	0.942 (6)	0.4008 (5)	0.099 (14)*
H1W1	0.618 (3)	0.673 (6)	0.302 (3)	0.18 (3)*
H1W2	0.768 (5)	0.707 (5)	0.289 (3)	0.16 (3)*
H2W1	0.999 (3)	0.938 (7)	0.293 (3)	0.15 (2)*
H2W2	0.846 (5)	0.962 (6)	0.267 (3)	0.18 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.0352 (3)	0.0286 (3)	0.0336 (3)	−0.00023 (16)	−0.00054 (18)	0.00020 (16)
O1	0.0570 (10)	0.0483 (10)	0.0497 (10)	−0.0058 (8)	0.0094 (8)	0.0037 (8)
O2	0.0857 (15)	0.0434 (11)	0.0640 (13)	0.0118 (10)	0.0091 (11)	0.0072 (10)
O4	0.0827 (17)	0.104 (2)	0.0663 (14)	0.0189 (16)	0.0038 (12)	0.0144 (14)
O3	0.0739 (14)	0.0960 (18)	0.0556 (12)	0.0097 (13)	0.0092 (10)	0.0063 (11)
O1W	0.0770 (18)	0.090 (2)	0.117 (2)	−0.0004 (17)	0.0123 (16)	−0.0084 (18)
O2W	0.0751 (18)	0.111 (2)	0.104 (2)	−0.0018 (18)	0.0148 (15)	0.0180 (18)
N1	0.0544 (12)	0.0512 (12)	0.0458 (11)	−0.0050 (10)	0.0060 (9)	−0.0008 (9)
N2	0.0530 (13)	0.0406 (12)	0.0534 (13)	−0.0057 (9)	0.0044 (10)	0.0005 (8)
C1	0.0692 (18)	0.0698 (19)	0.0476 (14)	−0.0067 (15)	0.0041 (12)	0.0012 (13)
C2	0.086 (2)	0.082 (2)	0.0494 (15)	−0.0158 (19)	0.0158 (14)	−0.0107 (15)
C3	0.084 (2)	0.062 (2)	0.072 (2)	−0.0118 (17)	0.0297 (17)	−0.0221 (16)
C4	0.0728 (19)	0.0449 (15)	0.0707 (18)	−0.0061 (13)	0.0206 (15)	−0.0075 (13)
C5	0.0535 (14)	0.0433 (13)	0.0538 (14)	−0.0086 (11)	0.0105 (11)	−0.0015 (11)
C6	0.0653 (17)	0.0499 (16)	0.0683 (17)	−0.0123 (13)	0.0068 (13)	−0.0003 (13)
C7	0.066 (2)	0.068 (2)	0.085 (2)	−0.0239 (17)	0.0023 (16)	−0.0067 (17)
C8	0.0488 (18)	0.090 (3)	0.087 (3)	−0.0133 (16)	−0.0091 (17)	0.0040 (18)
C9	0.0532 (16)	0.071 (2)	0.0696 (18)	0.0047 (15)	0.0026 (13)	0.0081 (16)
C10	0.0501 (13)	0.0488 (14)	0.0478 (13)	0.0008 (11)	0.0072 (10)	0.0029 (11)
C11	0.0580 (15)	0.0391 (13)	0.0513 (13)	0.0019 (11)	0.0066 (11)	0.0027 (10)
C12	0.0698 (19)	0.071 (2)	0.0564 (16)	−0.0037 (16)	0.0025 (14)	0.0047 (14)
C13	0.137 (4)	0.127 (4)	0.061 (2)	0.016 (3)	0.012 (2)	0.015 (2)

Geometric parameters (Å, º)

Mn1—N1	2.025 (2)	C1—H1	0.9300
Mn1—N1^i	2.025 (2)	C2—C3	1.376 (5)
Mn1—N2	2.002 (3)	C2—H2	0.9300
Mn1—N2^i	2.002 (3)	C3—C4	1.382 (4)
Mn1—O1^i	2.409 (2)	C3—H3	0.9300
Mn1—O1	2.409 (2)	C4—C5	1.388 (4)
O1—C11	1.415 (3)	C4—H4	0.9300
O1—H1O	0.870 (10)	C5—C11	1.519 (4)
O2—C11	1.377 (3)	C6—C7	1.363 (4)
O2—H2O	0.858 (10)	C6—H6	0.9300
O4—C12	1.259 (4)	C7—C8	1.360 (5)
O3—C12	1.246 (4)	C7—H7	0.9300
O1W—H1W1	0.854 (10)	C8—C9	1.368 (5)
O1W—H1W2	0.854 (10)	C8—H8A	0.9300
O2W—H2W1	0.856 (10)	C9—C10	1.374 (4)
O2W—H2W2	0.852 (10)	C9—H9A	0.9300
N1—C1	1.335 (3)	C10—C11	1.548 (4)
N1—C5	1.342 (4)	C12—C13	1.508 (5)
N2—C10	1.341 (3)	C13—H13A	0.9600
N2—C6	1.343 (4)	C13—H13B	0.9600
C1—C2	1.389 (5)	C13—H13C	0.9600
N1—Mn1—N2	88.03 (9)	C3—C4—C5	117.9 (3)
N1—Mn1—N2^i	91.97 (9)	C3—C4—H4	121.0
N1—Mn1—O1	73.94 (8)	C5—C4—H4	121.0
N1—Mn1—O1^i	106.06 (8)	N1—C5—C4	122.0 (3)
N2—Mn1—O1	75.67 (7)	N1—C5—C11	114.8 (2)
N2—Mn1—O1^i	104.33 (8)	C4—C5—C11	123.2 (3)
N2—Mn1—N2^i	180	N2—C6—C7	121.7 (3)
N2—Mn1—N1^i	91.97 (9)	N2—C6—H6	119.1
N2^i—Mn1—N1^i	88.03 (9)	C7—C6—H6	119.1
N1—Mn1—N1^i	180	C8—C7—C6	118.6 (3)
N2^i—Mn1—O1^i	75.67 (7)	C8—C7—H7	120.7
N1^i—Mn1—O1^i	73.94 (8)	C6—C7—H7	120.7
N2^i—Mn1—O1	104.33 (8)	C7—C8—C9	120.6 (3)
N1^i—Mn1—O1	106.06 (8)	C7—C8—H8A	119.7
O1^i—Mn1—O1	180	C9—C8—H8A	119.7
C11—O1—Mn1	93.64 (13)	C8—C9—C10	118.6 (3)
C11—O1—H1O	108 (2)	C8—C9—H9A	120.7
Mn1—O1—H1O	121 (2)	C10—C9—H9A	120.7
C11—O2—H2O	116 (3)	N2—C10—C9	121.1 (3)
H1W1—O1W—H1W2	109.5 (18)	N2—C10—C11	113.8 (2)
H2W1—O2W—H2W2	109.4 (18)	C9—C10—C11	125.1 (3)
C1—N1—C5	119.8 (2)	O2—C11—O1	113.5 (2)
C1—N1—Mn1	125.3 (2)	O2—C11—C5	109.6 (2)
C5—N1—Mn1	114.93 (16)	O1—C11—C5	105.0 (2)
C10—N2—C6	119.4 (3)	O2—C11—C10	112.1 (2)
C10—N2—Mn1	116.02 (17)	O1—C11—C10	108.2 (2)
C6—N2—Mn1	124.6 (2)	C5—C11—C10	108.0 (2)
N1—C1—C2	121.3 (3)	O3—C12—O4	123.4 (3)
N1—C1—H1	119.3	O3—C12—C13	118.4 (3)
C2—C1—H1	119.3	O4—C12—C13	118.2 (3)
C3—C2—C1	118.9 (3)	C12—C13—H13A	109.5
C3—C2—H2	120.5	C12—C13—H13B	109.5
C1—C2—H2	120.5	H13A—C13—H13B	109.5
C2—C3—C4	120.1 (3)	C12—C13—H13C	109.5
C2—C3—H3	120.0	H13A—C13—H13C	109.5
C4—C3—H3	120.0	H13B—C13—H13C	109.5
N2—Mn1—O1—C11	44.65 (15)	C3—C4—C5—N1	0.1 (4)
N2^i—Mn1—O1—C11	−135.35 (15)	C3—C4—C5—C11	−179.9 (3)
N1—Mn1—O1—C11	−47.45 (14)	C10—N2—C6—C7	0.9 (5)
N1^i—Mn1—O1—C11	132.55 (14)	Mn1—N2—C6—C7	−179.0 (2)
N2—Mn1—N1—C1	130.6 (2)	N2—C6—C7—C8	−0.7 (5)
N2^i—Mn1—N1—C1	−49.4 (2)	C6—C7—C8—C9	−0.8 (7)
O1^i—Mn1—N1—C1	26.3 (2)	C7—C8—C9—C10	2.1 (6)
O1—Mn1—N1—C1	−153.7 (2)	C6—N2—C10—C9	0.4 (4)
N2—Mn1—N1—C5	−50.88 (19)	Mn1—N2—C10—C9	−179.6 (2)
N2^i—Mn1—N1—C5	129.12 (19)	C6—N2—C10—C11	−179.7 (2)
O1^i—Mn1—N1—C5	−155.22 (18)	Mn1—N2—C10—C11	0.2 (3)
O1—Mn1—N1—C5	24.78 (18)	C8—C9—C10—N2	−1.9 (5)
N1—Mn1—N2—C10	49.2 (2)	C8—C9—C10—C11	178.2 (3)
N1^i—Mn1—N2—C10	−130.8 (2)	Mn1—O1—C11—O2	179.20 (19)
O1^i—Mn1—N2—C10	155.31 (19)	Mn1—O1—C11—C5	59.45 (18)
O1—Mn1—N2—C10	−24.69 (19)	Mn1—O1—C11—C10	−55.69 (18)
N1—Mn1—N2—C6	−130.8 (3)	N1—C5—C11—O2	−172.1 (2)
N1^i—Mn1—N2—C6	49.2 (3)	C4—C5—C11—O2	7.8 (4)
O1^i—Mn1—N2—C6	−24.7 (3)	N1—C5—C11—O1	−49.9 (3)
O1—Mn1—N2—C6	155.3 (3)	C4—C5—C11—O1	130.1 (3)
C5—N1—C1—C2	−0.8 (4)	N1—C5—C11—C10	65.4 (3)
Mn1—N1—C1—C2	177.7 (2)	C4—C5—C11—C10	−114.6 (3)
N1—C1—C2—C3	0.1 (5)	N2—C10—C11—O2	171.8 (2)
C1—C2—C3—C4	0.6 (5)	C9—C10—C11—O2	−8.3 (4)
C2—C3—C4—C5	−0.7 (5)	N2—C10—C11—O1	45.9 (3)
C1—N1—C5—C4	0.6 (4)	C9—C10—C11—O1	−134.2 (3)
Mn1—N1—C5—C4	−177.9 (2)	N2—C10—C11—C5	−67.3 (3)
C1—N1—C5—C11	−179.4 (2)	C9—C10—C11—C5	112.6 (3)
Mn1—N1—C5—C11	2.0 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O3	0.87 (1)	1.73 (1)	2.595 (3)	179 (4)
O2—H2o···O4	0.86 (1)	1.76 (2)	2.605 (3)	166 (5)
O1w—H1w1···O3	0.85 (1)	1.92 (2)	2.757 (4)	168 (6)
O1w—H1w2···O2w	0.85 (1)	1.91 (1)	2.758 (5)	172 (6)
O2w—H2w1···O4^ii	0.86 (1)	2.01 (3)	2.788 (4)	150 (5)
O2w—H2w2···O1w^iii	0.85 (1)	1.96 (4)	2.737 (5)	150 (7)

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