Aqua­[bis(5-bromo­salicyl­idene)­ethyl­enediaminato]­chloro­manganese(III)

Dang, L.-L.; Huo, Y.-Q.; Wang, W.; Li, J.

doi:10.1107/S1600536805000942

Aqua[bis(5-bromosalicylidene)ethylenediaminato]chloromanganese(III)

L.-L. Dang, Y.-Q. Huo, W. Wang and J. Li

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805000942/br6176sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805000942/br6176Isup2.hkl Contains datablock I

CCDC reference: 263562

checkCIF report

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

Computing details top

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(C₁₆H₁₂Br₂N₂O₂)Cl(H₂O)] top

Crystal data top

[Mn(C₁₆H₁₂Br₂N₂O₂)Cl(H₂O)]	F(000) = 1040
M_r = 532.50	D_x = 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	R_int = 0.055
φ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) [please provide reference used with SMART CCD]	h = −12→14
T_min = 0.280, T_max = 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(F_o²) + (0.0365P)² + 25.603P] where P = (F_o² + 2F_c²)/3
3134 reflections	(Δ/σ)_max = 0.001
232 parameters	Δρ_max = 1.16 e Å⁻³
0 restraints	Δρ_min = −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	U_iso*/U_eq
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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Aqua­[bis(5-bromo­salicyl­idene)­ethyl­enediaminato]­chloro­manganese(III)

Supporting information

Key indicators

checkCIF/PLATON results

Aqua[bis(5-bromosalicylidene)ethylenediaminato]chloromanganese(III)