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The title compound (systematic name: aqua{4,4'-dibromo-2,2'-[1,2-ethanediylbis(nitrilomethylidyne)]diphenolato]chloromanganese(III)), [Mn(C16H12Br2N2O2)Cl(H2O)] or [Mn(Br2salen)Cl(H2O)], was prepared from a methanol solution. The Mn3+ ion displays an elongated octahedral geometry, coordinated by two N and two O atoms from salen, one O atom from the water ligand and one Cl- anion, and is slightly displaced out of the Schiff base N2O2 plane toward the axial Cl- ion. Hydrogen bonds between the coordinated water O and Cl atoms link pairs of molecules into a three-dimensional network.
Supporting information
CCDC reference: 263562
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.014 Å
- R factor = 0.073
- wR factor = 0.164
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 14
PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Cl1 .. 3.33 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
1 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
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1994); cell refinement: SMART; data reduction: SMART; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: please provide; software used to prepare material for publication: SHELXL97.
aqua{4,4'-dibromo-2,2'-[1,2-
ethanediylbis(nitrilomethylidyne)]diphenolato]chloromanganese(III)),
[Mn(C
16H
12Br
2N
2O
2)Cl(H
2O)]
top
Crystal data top
[Mn(C16H12Br2N2O2)Cl(H2O)] | F(000) = 1040 |
Mr = 532.50 | Dx = 1.978 Mg m−3 |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yab | Cell parameters from 8335 reflections |
a = 12.2994 (18) Å | θ = 3.1–27.5° |
b = 11.6445 (17) Å | µ = 5.37 mm−1 |
c = 13.660 (2) Å | T = 293 K |
β = 113.909 (2)° | Block, brown |
V = 1788.5 (5) Å3 | 0.3 × 0.2 × 0.1 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector [Please confirm machine type] diffractometer | 3134 independent reflections |
Radiation source: fine-focus sealed tube | 2766 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
φ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) [please provide reference used with SMART CCD] | h = −12→14 |
Tmin = 0.280, Tmax = 0.584 | k = −13→13 |
7093 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.073 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.19 | w = 1/[σ2(Fo2) + (0.0365P)2 + 25.603P] where P = (Fo2 + 2Fc2)/3 |
3134 reflections | (Δ/σ)max = 0.001 |
232 parameters | Δρmax = 1.16 e Å−3 |
0 restraints | Δρmin = −1.32 e Å−3 |
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 | |
Br1 | 0.29104 (9) | 0.42081 (9) | −0.10650 (8) | 0.0345 (3) | |
Br2 | 0.55021 (9) | 0.85781 (9) | 0.97316 (8) | 0.0374 (3) | |
Mn1 | 0.45013 (11) | 0.70293 (11) | 0.41878 (11) | 0.0227 (3) | |
Cl1 | 0.28528 (19) | 0.85780 (19) | 0.36339 (19) | 0.0292 (5) | |
O1 | 0.3552 (5) | 0.5861 (5) | 0.3311 (5) | 0.0266 (14) | |
O2 | 0.4231 (5) | 0.6492 (5) | 0.5364 (5) | 0.0246 (13) | |
O1W | 0.6167 (6) | 0.5922 (6) | 0.4765 (6) | 0.0356 (17) | |
H1W1 | 0.590 (10) | 0.524 (10) | 0.467 (9) | 0.043* | |
H1W2 | 0.664 (10) | 0.599 (10) | 0.452 (9) | 0.043* | |
N1 | 0.4957 (6) | 0.7610 (7) | 0.3047 (6) | 0.0260 (16) | |
N2 | 0.5615 (6) | 0.8238 (6) | 0.5052 (6) | 0.0222 (15) | |
C1 | 0.3482 (8) | 0.5523 (8) | 0.2360 (8) | 0.029 (2) | |
C2 | 0.2853 (9) | 0.4504 (8) | 0.1939 (8) | 0.033 (2) | |
H2 | 0.2530 | 0.4092 | 0.2340 | 0.039* | |
C3 | 0.2706 (8) | 0.4106 (8) | 0.0945 (8) | 0.029 (2) | |
H3 | 0.2261 | 0.3448 | 0.0661 | 0.034* | |
C4 | 0.3238 (8) | 0.4707 (8) | 0.0368 (7) | 0.029 (2) | |
C5 | 0.3866 (9) | 0.5677 (8) | 0.0746 (8) | 0.033 (2) | |
H5 | 0.4193 | 0.6071 | 0.0339 | 0.040* | |
C6 | 0.4023 (7) | 0.6092 (8) | 0.1774 (7) | 0.0261 (19) | |
C7 | 0.4728 (7) | 0.7127 (8) | 0.2146 (7) | 0.0247 (19) | |
H7 | 0.5036 | 0.7463 | 0.1695 | 0.030* | |
C8 | 0.5587 (8) | 0.8724 (8) | 0.3303 (8) | 0.030 (2) | |
H8A | 0.5018 | 0.9350 | 0.3078 | 0.036* | |
H8B | 0.6107 | 0.8794 | 0.2929 | 0.036* | |
C9 | 0.6309 (9) | 0.8778 (8) | 0.4502 (8) | 0.030 (2) | |
H9A | 0.7056 | 0.8374 | 0.4688 | 0.036* | |
H9B | 0.6484 | 0.9571 | 0.4728 | 0.036* | |
C10 | 0.5808 (7) | 0.8501 (7) | 0.6008 (7) | 0.0221 (18) | |
H10 | 0.6347 | 0.9090 | 0.6324 | 0.027* | |
C11 | 0.5265 (8) | 0.7966 (7) | 0.6648 (7) | 0.0244 (18) | |
C12 | 0.5570 (8) | 0.8404 (8) | 0.7684 (8) | 0.028 (2) | |
H12 | 0.6088 | 0.9025 | 0.7917 | 0.034* | |
C13 | 0.5114 (8) | 0.7929 (8) | 0.8357 (7) | 0.0276 (19) | |
C14 | 0.4367 (8) | 0.6976 (8) | 0.8038 (7) | 0.027 (2) | |
H14 | 0.4062 | 0.6658 | 0.8499 | 0.033* | |
C15 | 0.4080 (8) | 0.6503 (8) | 0.7038 (7) | 0.0269 (19) | |
H15 | 0.3585 | 0.5864 | 0.6830 | 0.032* | |
C16 | 0.4533 (8) | 0.6982 (7) | 0.6320 (7) | 0.0232 (18) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0359 (5) | 0.0359 (5) | 0.0295 (5) | 0.0040 (4) | 0.0110 (4) | −0.0049 (4) |
Br2 | 0.0431 (6) | 0.0404 (6) | 0.0299 (5) | −0.0048 (5) | 0.0161 (4) | −0.0084 (4) |
Mn1 | 0.0223 (7) | 0.0210 (7) | 0.0277 (7) | −0.0026 (5) | 0.0132 (6) | 0.0001 (5) |
Cl1 | 0.0281 (11) | 0.0283 (11) | 0.0356 (12) | 0.0056 (9) | 0.0173 (10) | 0.0046 (9) |
O1 | 0.033 (3) | 0.027 (3) | 0.026 (3) | −0.003 (3) | 0.017 (3) | −0.002 (3) |
O2 | 0.026 (3) | 0.022 (3) | 0.027 (3) | 0.000 (3) | 0.011 (3) | 0.001 (3) |
O1W | 0.034 (4) | 0.027 (4) | 0.059 (5) | 0.001 (3) | 0.033 (4) | 0.007 (3) |
N1 | 0.020 (4) | 0.033 (4) | 0.028 (4) | −0.001 (3) | 0.012 (3) | 0.000 (3) |
N2 | 0.020 (4) | 0.017 (3) | 0.032 (4) | 0.004 (3) | 0.014 (3) | 0.005 (3) |
C1 | 0.026 (5) | 0.025 (5) | 0.041 (6) | −0.002 (4) | 0.017 (4) | −0.002 (4) |
C2 | 0.035 (5) | 0.029 (5) | 0.035 (5) | −0.003 (4) | 0.015 (4) | 0.000 (4) |
C3 | 0.019 (4) | 0.030 (5) | 0.037 (5) | −0.004 (4) | 0.011 (4) | −0.003 (4) |
C4 | 0.025 (5) | 0.038 (5) | 0.021 (5) | 0.006 (4) | 0.006 (4) | −0.001 (4) |
C5 | 0.033 (5) | 0.029 (5) | 0.043 (6) | 0.001 (4) | 0.022 (5) | −0.001 (4) |
C6 | 0.019 (4) | 0.035 (5) | 0.028 (5) | 0.008 (4) | 0.012 (4) | 0.000 (4) |
C7 | 0.022 (4) | 0.029 (5) | 0.031 (5) | 0.002 (4) | 0.018 (4) | 0.005 (4) |
C8 | 0.030 (5) | 0.023 (4) | 0.036 (5) | −0.007 (4) | 0.014 (4) | −0.002 (4) |
C9 | 0.039 (5) | 0.022 (4) | 0.037 (5) | −0.005 (4) | 0.024 (5) | 0.001 (4) |
C10 | 0.019 (4) | 0.015 (4) | 0.034 (5) | 0.000 (3) | 0.012 (4) | 0.001 (4) |
C11 | 0.024 (4) | 0.020 (4) | 0.030 (5) | 0.002 (4) | 0.012 (4) | 0.002 (4) |
C12 | 0.025 (5) | 0.022 (5) | 0.035 (5) | 0.003 (4) | 0.010 (4) | 0.003 (4) |
C13 | 0.031 (5) | 0.029 (5) | 0.023 (5) | 0.001 (4) | 0.010 (4) | 0.004 (4) |
C14 | 0.026 (5) | 0.030 (5) | 0.033 (5) | 0.006 (4) | 0.019 (4) | 0.010 (4) |
C15 | 0.028 (5) | 0.028 (5) | 0.024 (5) | 0.000 (4) | 0.010 (4) | 0.005 (4) |
C16 | 0.027 (4) | 0.019 (4) | 0.025 (5) | 0.002 (4) | 0.011 (4) | −0.001 (3) |
Geometric parameters (Å, º) top
Br1—C4 | 1.921 (9) | C4—C5 | 1.347 (13) |
Br2—C13 | 1.896 (9) | C5—C6 | 1.421 (13) |
Mn1—O1 | 1.875 (6) | C5—H5 | 0.9300 |
Mn1—O2 | 1.875 (6) | C6—C7 | 1.451 (13) |
Mn1—N1 | 1.978 (7) | C7—H7 | 0.9300 |
Mn1—N2 | 1.985 (7) | C8—C9 | 1.516 (13) |
Mn1—O1W | 2.274 (7) | C8—H8A | 0.9700 |
Mn1—Cl1 | 2.587 (3) | C8—H8B | 0.9700 |
O1—C1 | 1.326 (11) | C9—H9A | 0.9700 |
O2—C16 | 1.331 (10) | C9—H9B | 0.9700 |
O1W—H1W1 | 0.85 (12) | C10—C11 | 1.439 (12) |
O1W—H1W2 | 0.78 (12) | C10—H10 | 0.9300 |
N1—C7 | 1.276 (11) | C11—C12 | 1.405 (13) |
N1—C8 | 1.479 (11) | C11—C16 | 1.413 (12) |
N2—C10 | 1.267 (11) | C12—C13 | 1.373 (13) |
N2—C9 | 1.486 (11) | C12—H12 | 0.9300 |
C1—C6 | 1.398 (12) | C13—C14 | 1.393 (13) |
C1—C2 | 1.405 (13) | C14—C15 | 1.380 (13) |
C2—C3 | 1.376 (13) | C14—H14 | 0.9300 |
C2—H2 | 0.9300 | C15—C16 | 1.424 (12) |
C3—C4 | 1.399 (13) | C15—H15 | 0.9300 |
C3—H3 | 0.9300 | | |
| | | |
O1—Mn1—O2 | 91.4 (3) | C6—C5—H5 | 120.3 |
O1—Mn1—N1 | 92.7 (3) | C1—C6—C5 | 119.9 (9) |
O2—Mn1—N1 | 174.2 (3) | C1—C6—C7 | 123.2 (8) |
O1—Mn1—N2 | 174.5 (3) | C5—C6—C7 | 116.8 (8) |
O2—Mn1—N2 | 92.6 (3) | N1—C7—C6 | 124.8 (8) |
N1—Mn1—N2 | 83.0 (3) | N1—C7—H7 | 117.6 |
O1—Mn1—O1W | 92.9 (3) | C6—C7—H7 | 117.6 |
O2—Mn1—O1W | 87.8 (3) | N1—C8—C9 | 108.2 (7) |
N1—Mn1—O1W | 87.9 (3) | N1—C8—H8A | 110.0 |
N2—Mn1—O1W | 83.6 (3) | C9—C8—H8A | 110.0 |
O1—Mn1—Cl1 | 96.2 (2) | N1—C8—H8B | 110.0 |
O2—Mn1—Cl1 | 95.33 (19) | C9—C8—H8B | 110.0 |
N1—Mn1—Cl1 | 88.3 (2) | H8A—C8—H8B | 108.4 |
N2—Mn1—Cl1 | 87.1 (2) | N2—C9—C8 | 108.9 (8) |
O1W—Mn1—Cl1 | 170.3 (2) | N2—C9—H9A | 109.9 |
C1—O1—Mn1 | 128.1 (5) | C8—C9—H9A | 109.9 |
C16—O2—Mn1 | 128.4 (5) | N2—C9—H9B | 109.9 |
Mn1—O1W—H1W1 | 104 (8) | C8—C9—H9B | 109.9 |
Mn1—O1W—H1W2 | 121 (9) | H9A—C9—H9B | 108.3 |
H1W1—O1W—H1W2 | 109 (10) | N2—C10—C11 | 125.6 (8) |
C7—N1—C8 | 120.3 (8) | N2—C10—H10 | 117.2 |
C7—N1—Mn1 | 125.9 (6) | C11—C10—H10 | 117.2 |
C8—N1—Mn1 | 113.7 (6) | C12—C11—C16 | 119.4 (8) |
C10—N2—C9 | 120.9 (7) | C12—C11—C10 | 117.0 (8) |
C10—N2—Mn1 | 125.5 (6) | C16—C11—C10 | 123.4 (8) |
C9—N2—Mn1 | 113.5 (6) | C13—C12—C11 | 120.9 (8) |
O1—C1—C6 | 124.3 (8) | C13—C12—H12 | 119.6 |
O1—C1—C2 | 117.2 (8) | C11—C12—H12 | 119.6 |
C6—C1—C2 | 118.4 (9) | C12—C13—C14 | 120.5 (9) |
C3—C2—C1 | 121.2 (9) | C12—C13—Br2 | 119.6 (7) |
C3—C2—H2 | 119.4 | C14—C13—Br2 | 119.8 (7) |
C1—C2—H2 | 119.4 | C15—C14—C13 | 120.0 (8) |
C2—C3—C4 | 118.9 (9) | C15—C14—H14 | 120.0 |
C2—C3—H3 | 120.6 | C13—C14—H14 | 120.0 |
C4—C3—H3 | 120.6 | C14—C15—C16 | 120.8 (8) |
C5—C4—C3 | 122.0 (9) | C14—C15—H15 | 119.6 |
C5—C4—Br1 | 119.7 (7) | C16—C15—H15 | 119.6 |
C3—C4—Br1 | 118.0 (7) | O2—C16—C11 | 123.2 (8) |
C4—C5—C6 | 119.4 (9) | O2—C16—C15 | 118.4 (8) |
C4—C5—H5 | 120.3 | C11—C16—C15 | 118.4 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O2i | 0.85 (12) | 2.02 (12) | 2.847 (9) | 164 (11) |
O1W—H1W2···Cl1ii | 0.78 (12) | 2.32 (12) | 3.102 (7) | 171 (11) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1/2, −y+3/2, z. |
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