In the title complex, [Mn(C
3H
2O
4)(C
12H
8N
2)(H
2O)
2], the Mn
II atom displays a distorted octahedral geometry, being coordinated by two N atoms of a 1,10-phenanthroline ligand, two O atoms from the carboxylate groups of the chelating malonate dianion and two O atoms of
cis water molecules. The complex molecules are linked to form a three-dimensional supramolecular array
via O—H
O hydrogen bonds and π–π interactions.
Supporting information
CCDC reference: 252465
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.026
- wR factor = 0.071
- Data-to-parameter ratio = 12.4
checkCIF/PLATON results
No syntax errors found
Alert level C
SHFSU01_ALERT_2_C The absolute value of parameter shift to su ratio > 0.05
Absolute value of the parameter shift to su ratio given 0.061
Additional refinement cycles may be required.
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.64 Sigma
PLAT080_ALERT_2_C Maximum Shift/Error ............................ 0.06
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 10
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.07 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mn1 - N2 .. 5.16 su
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 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
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1994); software used to prepare material for publication: SHELXL97.
cis-Diaquamalonato(1,10-phenanthroline)manganese(II)
top
Crystal data top
[Mn(C3H2O4)(C12H8N2)(H2O)2] | F(000) = 764 |
Mr = 373.22 | Dx = 1.662 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.978 (5) Å | Cell parameters from 5579 reflections |
b = 9.918 (4) Å | θ = 2.1–27.5° |
c = 15.426 (7) Å | µ = 0.92 mm−1 |
β = 102.310 (7)° | T = 293 K |
V = 1491.6 (11) Å3 | Prism, yellow |
Z = 4 | 0.31 × 0.19 × 0.11 mm |
Data collection top
Siemens SMART CCD diffractometer | 3410 independent reflections |
Radiation source: fine-focus sealed tube | 3244 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ω scans | θmax = 27.5°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→11 |
Tmin = 0.812, Tmax = 0.904 | k = −11→12 |
11205 measured reflections | l = −20→15 |
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)] = 0.027 | All H-atom parameters refined |
wR(F2) = 0.071 | w = 1/[σ2(Fo2) + (0.0396P)2 + 0.4812P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.061 |
3410 reflections | Δρmax = 0.39 e Å−3 |
274 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0029 (11) |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
Mn1 | 0.150822 (19) | 0.091860 (19) | 0.228252 (12) | 0.01190 (9) | |
O1 | 0.19337 (10) | 0.06040 (10) | 0.09879 (6) | 0.0178 (2) | |
O2 | 0.17559 (10) | 0.12817 (10) | −0.04101 (6) | 0.0167 (2) | |
O3 | 0.08152 (10) | 0.28745 (9) | 0.17840 (6) | 0.0154 (2) | |
O4 | −0.03919 (12) | 0.41947 (10) | 0.07342 (7) | 0.0239 (2) | |
O5 | −0.03719 (10) | −0.02709 (10) | 0.20142 (7) | 0.0176 (2) | |
O6 | 0.07574 (11) | 0.14840 (11) | 0.34745 (7) | 0.0186 (2) | |
N1 | 0.35656 (11) | 0.17970 (12) | 0.29494 (7) | 0.0145 (2) | |
N2 | 0.27963 (12) | −0.08374 (11) | 0.29568 (8) | 0.0142 (2) | |
C1 | 0.13229 (13) | 0.12232 (13) | 0.02990 (8) | 0.0135 (3) | |
C2 | −0.00156 (13) | 0.19474 (14) | 0.03245 (9) | 0.0148 (3) | |
C3 | 0.01520 (13) | 0.31095 (13) | 0.09930 (9) | 0.0144 (3) | |
C4 | 0.39219 (14) | 0.30877 (14) | 0.29535 (9) | 0.0176 (3) | |
C5 | 0.51838 (15) | 0.35761 (15) | 0.34289 (10) | 0.0206 (3) | |
C6 | 0.61059 (15) | 0.26842 (16) | 0.39045 (10) | 0.0220 (3) | |
C7 | 0.57646 (14) | 0.13081 (16) | 0.39173 (9) | 0.0189 (3) | |
C8 | 0.66673 (15) | 0.03171 (17) | 0.44114 (10) | 0.0248 (3) | |
C9 | 0.62720 (16) | −0.09797 (17) | 0.44259 (10) | 0.0246 (3) | |
C10 | 0.49590 (15) | −0.14222 (15) | 0.39433 (9) | 0.0189 (3) | |
C11 | 0.45158 (16) | −0.27744 (16) | 0.39392 (10) | 0.0238 (3) | |
C12 | 0.32530 (16) | −0.31218 (15) | 0.34504 (11) | 0.0239 (3) | |
C13 | 0.24202 (15) | −0.21224 (14) | 0.29590 (10) | 0.0188 (3) | |
C14 | 0.40511 (13) | −0.04824 (14) | 0.34399 (8) | 0.0146 (3) | |
C15 | 0.44648 (14) | 0.09101 (13) | 0.34327 (9) | 0.0142 (3) | |
H2A | −0.0431 (16) | 0.2312 (16) | −0.0280 (11) | 0.014 (4)* | |
H2B | −0.0664 (19) | 0.1321 (19) | 0.0509 (12) | 0.026 (5)* | |
H4 | 0.3279 (16) | 0.3675 (18) | 0.2602 (11) | 0.015 (4)* | |
H5 | 0.5393 (18) | 0.4509 (19) | 0.3415 (12) | 0.023 (4)* | |
H5A | −0.071 (2) | −0.060 (2) | 0.1540 (16) | 0.043 (6)* | |
H5B | −0.056 (2) | −0.083 (2) | 0.2418 (15) | 0.041 (6)* | |
H6 | 0.697 (2) | 0.3005 (19) | 0.4210 (12) | 0.029 (5)* | |
H6A | 0.059 (2) | 0.079 (2) | 0.3745 (13) | 0.027 (5)* | |
H6B | 0.112 (2) | 0.208 (2) | 0.3838 (14) | 0.038 (6)* | |
H8 | 0.750 (2) | 0.060 (2) | 0.4710 (13) | 0.032 (5)* | |
H9 | 0.683 (2) | −0.162 (2) | 0.4741 (14) | 0.039 (5)* | |
H11 | 0.5106 (19) | −0.341 (2) | 0.4268 (13) | 0.030 (5)* | |
H12 | 0.295 (2) | −0.399 (2) | 0.3414 (14) | 0.035 (5)* | |
H13 | 0.1563 (17) | −0.2400 (17) | 0.2584 (12) | 0.018 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Mn1 | 0.01320 (12) | 0.01133 (12) | 0.01016 (12) | 0.00100 (7) | 0.00027 (8) | 0.00002 (7) |
O1 | 0.0234 (5) | 0.0175 (5) | 0.0118 (5) | 0.0061 (4) | 0.0024 (4) | 0.0009 (4) |
O2 | 0.0202 (5) | 0.0185 (5) | 0.0113 (5) | −0.0003 (4) | 0.0031 (4) | −0.0019 (4) |
O3 | 0.0200 (5) | 0.0133 (5) | 0.0117 (4) | 0.0035 (4) | 0.0003 (4) | −0.0007 (3) |
O4 | 0.0329 (6) | 0.0164 (5) | 0.0189 (5) | 0.0090 (4) | −0.0019 (4) | 0.0014 (4) |
O5 | 0.0222 (5) | 0.0170 (5) | 0.0121 (5) | −0.0060 (4) | −0.0001 (4) | 0.0005 (4) |
O6 | 0.0274 (5) | 0.0145 (5) | 0.0145 (5) | −0.0027 (4) | 0.0062 (4) | −0.0020 (4) |
N1 | 0.0151 (5) | 0.0155 (6) | 0.0126 (5) | 0.0000 (4) | 0.0024 (4) | 0.0003 (4) |
N2 | 0.0148 (5) | 0.0134 (6) | 0.0147 (6) | 0.0014 (4) | 0.0038 (4) | −0.0002 (4) |
C1 | 0.0167 (6) | 0.0107 (6) | 0.0118 (6) | −0.0023 (5) | 0.0000 (5) | −0.0025 (4) |
C2 | 0.0148 (6) | 0.0163 (6) | 0.0122 (6) | 0.0002 (5) | 0.0002 (5) | −0.0010 (5) |
C3 | 0.0149 (6) | 0.0148 (6) | 0.0139 (6) | −0.0002 (5) | 0.0041 (5) | 0.0001 (5) |
C4 | 0.0194 (7) | 0.0173 (7) | 0.0163 (7) | −0.0010 (5) | 0.0040 (5) | 0.0003 (5) |
C5 | 0.0230 (7) | 0.0194 (7) | 0.0207 (7) | −0.0076 (6) | 0.0076 (6) | −0.0042 (5) |
C6 | 0.0163 (7) | 0.0293 (8) | 0.0203 (7) | −0.0059 (6) | 0.0037 (5) | −0.0069 (6) |
C7 | 0.0153 (6) | 0.0255 (7) | 0.0152 (7) | 0.0005 (5) | 0.0017 (5) | −0.0027 (5) |
C8 | 0.0161 (7) | 0.0334 (9) | 0.0212 (7) | 0.0046 (6) | −0.0041 (6) | −0.0040 (6) |
C9 | 0.0218 (7) | 0.0296 (8) | 0.0194 (7) | 0.0127 (6) | −0.0021 (6) | 0.0002 (6) |
C10 | 0.0212 (7) | 0.0208 (7) | 0.0144 (6) | 0.0077 (6) | 0.0031 (5) | 0.0013 (5) |
C11 | 0.0296 (8) | 0.0196 (7) | 0.0220 (7) | 0.0116 (6) | 0.0051 (6) | 0.0042 (6) |
C12 | 0.0301 (8) | 0.0128 (7) | 0.0306 (8) | 0.0031 (6) | 0.0105 (6) | 0.0023 (6) |
C13 | 0.0194 (7) | 0.0157 (7) | 0.0224 (7) | 0.0012 (5) | 0.0072 (6) | −0.0011 (5) |
C14 | 0.0152 (6) | 0.0176 (7) | 0.0113 (6) | 0.0037 (5) | 0.0037 (5) | −0.0006 (5) |
C15 | 0.0137 (6) | 0.0182 (7) | 0.0106 (6) | 0.0012 (5) | 0.0022 (5) | −0.0005 (5) |
Geometric parameters (Å, º) top
Mn1—O3 | 2.1462 (12) | C2—H2B | 0.982 (19) |
Mn1—O1 | 2.1512 (13) | C4—C5 | 1.402 (2) |
Mn1—O5 | 2.1799 (12) | C4—H4 | 0.947 (17) |
Mn1—O6 | 2.2010 (13) | C5—C6 | 1.371 (2) |
Mn1—N1 | 2.2652 (14) | C5—H5 | 0.950 (18) |
Mn1—N2 | 2.2798 (13) | C6—C7 | 1.408 (2) |
O1—C1 | 1.2656 (16) | C6—H6 | 0.946 (19) |
O2—C1 | 1.2602 (17) | C7—C15 | 1.4083 (19) |
O3—C3 | 1.2794 (17) | C7—C8 | 1.437 (2) |
O4—C3 | 1.2329 (17) | C8—C9 | 1.347 (2) |
O5—H5A | 0.81 (2) | C8—H8 | 0.90 (2) |
O5—H5B | 0.88 (2) | C9—C10 | 1.431 (2) |
O6—H6A | 0.84 (2) | C9—H9 | 0.91 (2) |
O6—H6B | 0.84 (2) | C10—C14 | 1.4116 (19) |
N1—C4 | 1.3282 (19) | C10—C11 | 1.412 (2) |
N1—C15 | 1.3599 (17) | C11—C12 | 1.367 (2) |
N2—C13 | 1.3289 (18) | C11—H11 | 0.935 (19) |
N2—C14 | 1.3598 (18) | C12—C13 | 1.407 (2) |
C1—C2 | 1.5243 (19) | C12—H12 | 0.91 (2) |
C2—C3 | 1.5319 (19) | C13—H13 | 0.965 (17) |
C2—H2A | 1.004 (16) | C14—C15 | 1.442 (2) |
| | | |
O3—Mn1—O1 | 84.88 (4) | O4—C3—C2 | 117.49 (12) |
O3—Mn1—O5 | 102.87 (5) | O3—C3—C2 | 117.71 (12) |
O1—Mn1—O5 | 94.44 (4) | N1—C4—C5 | 123.04 (13) |
O3—Mn1—O6 | 85.87 (4) | N1—C4—H4 | 116.2 (11) |
O1—Mn1—O6 | 169.19 (4) | C5—C4—H4 | 120.7 (11) |
O5—Mn1—O6 | 82.19 (4) | C6—C5—C4 | 118.85 (14) |
O3—Mn1—N1 | 90.38 (4) | C6—C5—H5 | 121.0 (11) |
O1—Mn1—N1 | 97.95 (5) | C4—C5—H5 | 120.1 (10) |
O5—Mn1—N1 | 162.62 (4) | C5—C6—C7 | 119.76 (13) |
O6—Mn1—N1 | 87.68 (5) | C5—C6—H6 | 119.1 (12) |
O3—Mn1—N2 | 164.00 (4) | C7—C6—H6 | 121.1 (12) |
O1—Mn1—N2 | 96.27 (4) | C6—C7—C15 | 117.54 (13) |
O5—Mn1—N2 | 92.97 (5) | C6—C7—C8 | 122.98 (14) |
O6—Mn1—N2 | 94.17 (5) | C15—C7—C8 | 119.47 (14) |
N1—Mn1—N2 | 73.65 (5) | C9—C8—C7 | 120.61 (14) |
C1—O1—Mn1 | 123.65 (9) | C9—C8—H8 | 121.8 (13) |
C3—O3—Mn1 | 124.61 (8) | C7—C8—H8 | 117.6 (13) |
Mn1—O5—H5A | 124.6 (16) | C8—C9—C10 | 121.55 (14) |
Mn1—O5—H5B | 120.5 (14) | C8—C9—H9 | 121.7 (13) |
H5A—O5—H5B | 106 (2) | C10—C9—H9 | 116.7 (14) |
Mn1—O6—H6A | 110.2 (13) | C14—C10—C11 | 117.46 (13) |
Mn1—O6—H6B | 124.0 (14) | C14—C10—C9 | 119.52 (14) |
H6A—O6—H6B | 110.4 (19) | C11—C10—C9 | 123.02 (13) |
C4—N1—C15 | 118.44 (12) | C12—C11—C10 | 119.53 (13) |
C4—N1—Mn1 | 126.05 (9) | C12—C11—H11 | 122.0 (12) |
C15—N1—Mn1 | 115.36 (9) | C10—C11—H11 | 118.5 (12) |
C13—N2—C14 | 118.33 (12) | C11—C12—C13 | 119.25 (14) |
C13—N2—Mn1 | 127.00 (10) | C11—C12—H12 | 121.7 (13) |
C14—N2—Mn1 | 114.58 (9) | C13—C12—H12 | 119.0 (13) |
O2—C1—O1 | 123.94 (13) | N2—C13—C12 | 122.85 (14) |
O2—C1—C2 | 117.72 (11) | N2—C13—H13 | 119.1 (10) |
O1—C1—C2 | 118.34 (12) | C12—C13—H13 | 117.9 (10) |
C1—C2—C3 | 113.67 (11) | N2—C14—C10 | 122.58 (13) |
C1—C2—H2A | 109.6 (9) | N2—C14—C15 | 118.38 (12) |
C3—C2—H2A | 108.6 (9) | C10—C14—C15 | 119.04 (13) |
C1—C2—H2B | 110.1 (11) | N1—C15—C7 | 122.34 (13) |
C3—C2—H2B | 105.4 (11) | N1—C15—C14 | 117.86 (12) |
H2A—C2—H2B | 109.3 (14) | C7—C15—C14 | 119.80 (12) |
O4—C3—O3 | 124.77 (12) | | |
| | | |
O3—Mn1—O1—C1 | −25.11 (11) | C15—N1—C4—C5 | 0.3 (2) |
O5—Mn1—O1—C1 | 77.44 (11) | Mn1—N1—C4—C5 | 175.69 (10) |
O6—Mn1—O1—C1 | 6.1 (3) | N1—C4—C5—C6 | 0.8 (2) |
N1—Mn1—O1—C1 | −114.78 (11) | C4—C5—C6—C7 | −0.9 (2) |
N2—Mn1—O1—C1 | 170.92 (11) | C5—C6—C7—C15 | −0.2 (2) |
O1—Mn1—O3—C3 | 38.22 (11) | C5—C6—C7—C8 | −178.97 (14) |
O5—Mn1—O3—C3 | −55.18 (11) | C6—C7—C8—C9 | 177.70 (15) |
O6—Mn1—O3—C3 | −136.19 (11) | C15—C7—C8—C9 | −1.1 (2) |
N1—Mn1—O3—C3 | 136.16 (11) | C7—C8—C9—C10 | 1.0 (2) |
N2—Mn1—O3—C3 | 133.10 (14) | C8—C9—C10—C14 | −0.1 (2) |
O3—Mn1—N1—C4 | 2.06 (11) | C8—C9—C10—C11 | 179.57 (15) |
O1—Mn1—N1—C4 | 86.94 (11) | C14—C10—C11—C12 | 0.6 (2) |
O5—Mn1—N1—C4 | −138.01 (14) | C9—C10—C11—C12 | −179.04 (14) |
O6—Mn1—N1—C4 | −83.79 (11) | C10—C11—C12—C13 | 0.1 (2) |
N2—Mn1—N1—C4 | −178.82 (12) | C14—N2—C13—C12 | 1.1 (2) |
O3—Mn1—N1—C15 | 177.52 (9) | Mn1—N2—C13—C12 | −175.11 (11) |
O1—Mn1—N1—C15 | −97.59 (9) | C11—C12—C13—N2 | −1.1 (2) |
O5—Mn1—N1—C15 | 37.46 (19) | C13—N2—C14—C10 | −0.31 (19) |
O6—Mn1—N1—C15 | 91.67 (10) | Mn1—N2—C14—C10 | 176.39 (10) |
N2—Mn1—N1—C15 | −3.36 (9) | C13—N2—C14—C15 | 179.53 (12) |
O3—Mn1—N2—C13 | −176.72 (12) | Mn1—N2—C14—C15 | −3.77 (15) |
O1—Mn1—N2—C13 | −83.44 (12) | C11—C10—C14—N2 | −0.6 (2) |
O5—Mn1—N2—C13 | 11.36 (12) | C9—C10—C14—N2 | 179.12 (13) |
O6—Mn1—N2—C13 | 93.74 (12) | C11—C10—C14—C15 | 179.60 (13) |
N1—Mn1—N2—C13 | −179.91 (12) | C9—C10—C14—C15 | −0.7 (2) |
O3—Mn1—N2—C14 | 6.9 (2) | C4—N1—C15—C7 | −1.5 (2) |
O1—Mn1—N2—C14 | 100.20 (9) | Mn1—N1—C15—C7 | −177.33 (10) |
O5—Mn1—N2—C14 | −165.00 (9) | C4—N1—C15—C14 | 178.50 (12) |
O6—Mn1—N2—C14 | −82.63 (9) | Mn1—N1—C15—C14 | 2.66 (15) |
N1—Mn1—N2—C14 | 3.73 (9) | C6—C7—C15—N1 | 1.4 (2) |
Mn1—O1—C1—O2 | 163.40 (10) | C8—C7—C15—N1 | −179.75 (13) |
Mn1—O1—C1—C2 | −16.43 (16) | C6—C7—C15—C14 | −178.59 (13) |
O2—C1—C2—C3 | −115.93 (13) | C8—C7—C15—C14 | 0.3 (2) |
O1—C1—C2—C3 | 63.90 (16) | N2—C14—C15—N1 | 0.78 (18) |
Mn1—O3—C3—O4 | 170.69 (11) | C10—C14—C15—N1 | −179.37 (12) |
Mn1—O3—C3—C2 | −7.43 (16) | N2—C14—C15—C7 | −179.23 (12) |
C1—C2—C3—O4 | 132.16 (13) | C10—C14—C15—C7 | 0.62 (19) |
C1—C2—C3—O3 | −49.58 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O2i | 0.81 (2) | 1.95 (2) | 2.7529 (16) | 172 (2) |
O5—H5B···O3ii | 0.88 (2) | 1.83 (2) | 2.7140 (16) | 174 (2) |
O6—H6A···O4ii | 0.84 (2) | 1.81 (2) | 2.6397 (17) | 173 (2) |
O6—H6B···O2iii | 0.84 (2) | 2.02 (2) | 2.8519 (17) | 171 (2) |
Symmetry codes: (i) −x, −y, −z; (ii) −x, y−1/2, −z+1/2; (iii) x, −y+1/2, z+1/2. |