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metal-organic compounds
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].
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038724/sj2128sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038724/sj2128Isup2.hkl |
CCDC reference: 624997
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
Computing details top
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.
Crystal data top
[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) Å3 | 0.38 × 0.32 × 0.23 mm |
Z = 2 |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.173 | w = 1/[σ2(Fo2) + (0.1162P)2 + 0.3929P] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/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 (Å2) top
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 (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
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) top
Mn1—N1 | 2.025 (2) | C1—H1 | 0.9300 |
Mn1—N1i | 2.025 (2) | C2—C3 | 1.376 (5) |
Mn1—N2 | 2.002 (3) | C2—H2 | 0.9300 |
Mn1—N2i | 2.002 (3) | C3—C4 | 1.382 (4) |
Mn1—O1i | 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—N2i | 91.97 (9) | C3—C4—H4 | 121.0 |
N1—Mn1—O1 | 73.94 (8) | C5—C4—H4 | 121.0 |
N1—Mn1—O1i | 106.06 (8) | N1—C5—C4 | 122.0 (3) |
N2—Mn1—O1 | 75.67 (7) | N1—C5—C11 | 114.8 (2) |
N2—Mn1—O1i | 104.33 (8) | C4—C5—C11 | 123.2 (3) |
N2—Mn1—N2i | 180 | N2—C6—C7 | 121.7 (3) |
N2—Mn1—N1i | 91.97 (9) | N2—C6—H6 | 119.1 |
N2i—Mn1—N1i | 88.03 (9) | C7—C6—H6 | 119.1 |
N1—Mn1—N1i | 180 | C8—C7—C6 | 118.6 (3) |
N2i—Mn1—O1i | 75.67 (7) | C8—C7—H7 | 120.7 |
N1i—Mn1—O1i | 73.94 (8) | C6—C7—H7 | 120.7 |
N2i—Mn1—O1 | 104.33 (8) | C7—C8—C9 | 120.6 (3) |
N1i—Mn1—O1 | 106.06 (8) | C7—C8—H8A | 119.7 |
O1i—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) |
N2i—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) |
N1i—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) |
N2i—Mn1—N1—C1 | −49.4 (2) | C6—C7—C8—C9 | −0.8 (7) |
O1i—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) |
N2i—Mn1—N1—C5 | 129.12 (19) | C6—N2—C10—C11 | −179.7 (2) |
O1i—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) |
N1i—Mn1—N2—C10 | −130.8 (2) | Mn1—O1—C11—O2 | 179.20 (19) |
O1i—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) |
N1i—Mn1—N2—C6 | 49.2 (3) | C4—C5—C11—O2 | 7.8 (4) |
O1i—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) top
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···O4ii | 0.86 (1) | 2.01 (3) | 2.788 (4) | 150 (5) |
O2w—H2w2···O1wiii | 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. |
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