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In the title compound, [Mn(C11H9N2O4)2(H2O)4]·2H2O, the central MnII atom lies on a crystallographic inversion center and is coordinated by four water mol­ecules and two monodentate 1-(carboxy­meth­yl)-1,3-benzimidazol-3-ium-3-acetate ligands in a slightly distorted octa­hedral geometry. The crystal packing is stabilized by inter­molecular O—H...O hydrogen bonds, which generate a three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806040645/lh2192sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806040645/lh2192Isup2.hkl
Contains datablock I

CCDC reference: 627972

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.026
  • wR factor = 0.073
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mn1 - O3 .. 5.50 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Tetraaqua-bis[1-(carboxymethyl)-1,3-benzimidazol-3-ium-3-acetato-κO]manganese(II) dihydrate top
Crystal data top
[Mn(C11H9N2O4)2(H2O)4]·2H2F(000) = 654
Mr = 629.44Dx = 1.562 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3064 reflections
a = 5.4729 (6) Åθ = 2.6–27.5°
b = 11.7401 (14) ŵ = 0.57 mm1
c = 20.922 (3) ÅT = 291 K
β = 95.368 (1)°Block, pale yellow
V = 1338.4 (3) Å30.45 × 0.32 × 0.22 mm
Z = 2
Data collection top
Siemens SMART CCD area-detector
diffractometer
3064 independent reflections
Radiation source: fine-focus sealed tube2806 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ω and φ scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 77
Tmin = 0.782, Tmax = 0.886k = 1415
11525 measured reflectionsl = 2727
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0422P)2 + 0.3206P]
where P = (Fo2 + 2Fc2)/3
3064 reflections(Δ/σ)max < 0.001
211 parametersΔρmax = 0.30 e Å3
9 restraintsΔρmin = 0.30 e Å3
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
xyzUiso*/Ueq
Mn10.50000.50000.00000.02305 (9)
O10.51852 (18)0.69750 (9)0.48412 (5)0.0392 (2)
O20.7727 (2)0.68889 (12)0.40707 (6)0.0625 (4)
O30.75846 (16)0.53547 (9)0.08416 (4)0.0327 (2)
O40.93085 (18)0.59378 (10)0.17921 (4)0.0414 (2)
O50.39738 (18)0.33873 (8)0.04110 (5)0.0378 (2)
O60.19645 (16)0.59276 (8)0.03722 (5)0.0322 (2)
O71.01509 (19)0.70162 (10)0.29749 (5)0.0424 (2)
N10.58829 (18)0.48581 (9)0.24502 (5)0.0246 (2)
N20.53080 (19)0.51211 (9)0.34603 (5)0.0268 (2)
C10.7680 (2)0.42173 (10)0.28077 (5)0.0248 (2)
C20.9590 (2)0.35405 (11)0.26252 (7)0.0337 (3)
H20.98600.34360.21970.040*
C31.1060 (3)0.30339 (12)0.31191 (8)0.0437 (3)
H31.23670.25810.30200.052*
C41.0643 (3)0.31808 (13)0.37648 (8)0.0483 (4)
H41.16680.28150.40800.058*
C50.8755 (3)0.38522 (13)0.39480 (7)0.0405 (3)
H5A0.84740.39460.43760.049*
C60.7297 (2)0.43814 (10)0.34524 (6)0.0268 (2)
C70.4523 (2)0.53826 (11)0.28574 (5)0.0256 (2)
H70.32100.58640.27370.031*
C80.4356 (2)0.55926 (12)0.40365 (6)0.0338 (3)
H8A0.42850.49900.43520.041*
H8B0.26950.58620.39260.041*
C90.5908 (2)0.65751 (11)0.43393 (6)0.0310 (3)
C100.5488 (2)0.49154 (11)0.17477 (5)0.0285 (3)
H10A0.40150.53530.16270.034*
H10B0.52320.41510.15780.034*
C110.7660 (2)0.54626 (11)0.14457 (5)0.0260 (2)
H1W0.273 (2)0.3023 (15)0.0272 (9)0.067 (6)*
H3W0.073 (2)0.5682 (13)0.0536 (8)0.048 (5)*
H4W0.160 (3)0.6541 (10)0.0181 (8)0.053 (5)*
H2W0.507 (2)0.2925 (13)0.0552 (8)0.054 (5)*
H5W0.950 (3)0.6774 (18)0.2624 (5)0.065 (6)*
H6W0.921 (3)0.6925 (17)0.3262 (6)0.059 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.02303 (14)0.02746 (15)0.01852 (13)0.00319 (9)0.00120 (9)0.00136 (9)
O10.0419 (5)0.0441 (6)0.0323 (5)0.0033 (4)0.0070 (4)0.0138 (4)
O20.0638 (7)0.0727 (8)0.0559 (7)0.0389 (7)0.0319 (6)0.0356 (6)
O30.0290 (4)0.0508 (6)0.0186 (4)0.0076 (4)0.0026 (3)0.0002 (4)
O40.0383 (5)0.0601 (7)0.0256 (4)0.0212 (5)0.0023 (4)0.0054 (4)
O50.0326 (5)0.0339 (5)0.0456 (6)0.0055 (4)0.0032 (4)0.0123 (4)
O60.0290 (5)0.0338 (5)0.0354 (5)0.0016 (4)0.0108 (4)0.0005 (4)
O70.0391 (5)0.0514 (6)0.0370 (5)0.0011 (5)0.0047 (4)0.0073 (5)
N10.0245 (5)0.0293 (5)0.0202 (5)0.0013 (4)0.0030 (4)0.0005 (4)
N20.0303 (5)0.0290 (5)0.0219 (5)0.0040 (4)0.0059 (4)0.0042 (4)
C10.0269 (5)0.0232 (5)0.0241 (5)0.0030 (4)0.0014 (4)0.0009 (4)
C20.0319 (6)0.0292 (6)0.0405 (7)0.0005 (5)0.0055 (5)0.0067 (5)
C30.0357 (7)0.0282 (7)0.0657 (10)0.0060 (5)0.0030 (7)0.0034 (6)
C40.0528 (9)0.0348 (8)0.0534 (9)0.0049 (6)0.0164 (7)0.0098 (7)
C50.0523 (8)0.0387 (7)0.0286 (6)0.0031 (6)0.0061 (6)0.0062 (5)
C60.0310 (6)0.0246 (6)0.0245 (6)0.0041 (4)0.0012 (4)0.0001 (4)
C70.0248 (5)0.0272 (6)0.0252 (6)0.0018 (4)0.0044 (4)0.0006 (4)
C80.0358 (7)0.0416 (7)0.0256 (6)0.0074 (6)0.0114 (5)0.0101 (5)
C90.0326 (6)0.0332 (7)0.0276 (6)0.0007 (5)0.0043 (5)0.0056 (5)
C100.0274 (6)0.0394 (7)0.0187 (6)0.0063 (5)0.0014 (4)0.0001 (5)
C110.0253 (6)0.0316 (6)0.0210 (5)0.0013 (5)0.0018 (4)0.0007 (4)
Geometric parameters (Å, º) top
Mn1—O5i2.1749 (9)N2—C61.3936 (16)
Mn1—O52.1749 (9)N2—C81.4659 (15)
Mn1—O6i2.1895 (9)C1—C21.3947 (17)
Mn1—O62.1895 (9)C1—C61.3977 (16)
Mn1—O32.1929 (9)C2—C31.383 (2)
Mn1—O3i2.1929 (9)C2—H20.9300
O1—C91.2480 (15)C3—C41.402 (2)
O2—C91.2437 (17)C3—H30.9300
O3—C111.2671 (14)C4—C51.382 (2)
O4—C111.2362 (15)C4—H40.9300
O5—H1W0.831 (9)C5—C61.3939 (18)
O5—H2W0.841 (9)C5—H5A0.9300
O6—H3W0.838 (9)C7—H70.9300
O6—H4W0.838 (9)C8—C91.5339 (18)
O7—H5W0.835 (9)C8—H8A0.9700
O7—H6W0.832 (9)C8—H8B0.9700
N1—C71.3334 (15)C10—C111.5379 (16)
N1—C11.3982 (15)C10—H10A0.9700
N1—C101.4670 (15)C10—H10B0.9700
N2—C71.3298 (16)
O5i—Mn1—O5180C1—C2—H2122.0
O5i—Mn1—O6i93.43 (4)C2—C3—C4122.08 (14)
O5—Mn1—O6i86.57 (4)C2—C3—H3119.0
O5i—Mn1—O686.57 (4)C4—C3—H3119.0
O5—Mn1—O693.43 (4)C5—C4—C3122.08 (13)
O6i—Mn1—O6180C5—C4—H4119.0
O5i—Mn1—O388.92 (4)C3—C4—H4119.0
O5—Mn1—O391.08 (4)C4—C5—C6116.03 (13)
O6i—Mn1—O385.76 (4)C4—C5—H5A122.0
O6—Mn1—O394.24 (4)C6—C5—H5A122.0
O5i—Mn1—O3i91.08 (4)N2—C6—C5131.48 (12)
O5—Mn1—O3i88.92 (4)N2—C6—C1106.57 (10)
O6i—Mn1—O3i94.24 (4)C5—C6—C1121.96 (12)
O6—Mn1—O3i85.76 (4)N2—C7—N1110.44 (11)
O3—Mn1—O3i180N2—C7—H7124.8
C11—O3—Mn1141.11 (8)N1—C7—H7124.8
Mn1—O5—H1W122.8 (13)N2—C8—C9113.45 (10)
Mn1—O5—H2W119.9 (12)N2—C8—H8A108.9
H1W—O5—H2W108.8 (13)C9—C8—H8A108.9
Mn1—O6—H3W130.1 (11)N2—C8—H8B108.9
Mn1—O6—H4W114.3 (12)C9—C8—H8B108.9
H3W—O6—H4W109.0 (13)H8A—C8—H8B107.7
H5W—O7—H6W110.5 (14)O2—C9—O1126.79 (13)
C7—N1—C1108.27 (10)O2—C9—C8118.15 (11)
C7—N1—C10125.48 (10)O1—C9—C8115.05 (11)
C1—N1—C10126.22 (10)N1—C10—C11112.57 (9)
C7—N2—C6108.43 (10)N1—C10—H10A109.1
C7—N2—C8125.78 (11)C11—C10—H10A109.1
C6—N2—C8125.66 (11)N1—C10—H10B109.1
C2—C1—C6121.79 (11)C11—C10—H10B109.1
C2—C1—N1131.91 (11)H10A—C10—H10B107.8
C6—C1—N1106.29 (10)O4—C11—O3125.72 (11)
C3—C2—C1116.04 (13)O4—C11—C10119.82 (10)
C3—C2—H2122.0O3—C11—C10114.44 (10)
O5i—Mn1—O3—C11122.42 (15)C2—C1—C6—N2178.24 (11)
O5—Mn1—O3—C1157.58 (15)N1—C1—C6—N20.60 (12)
O6i—Mn1—O3—C11144.07 (15)C2—C1—C6—C51.91 (19)
O6—Mn1—O3—C1135.93 (15)N1—C1—C6—C5179.24 (12)
C7—N1—C1—C2178.11 (13)C6—N2—C7—N10.07 (14)
C10—N1—C1—C24.0 (2)C8—N2—C7—N1176.01 (11)
C7—N1—C1—C60.57 (13)C1—N1—C7—N20.32 (13)
C10—N1—C1—C6177.33 (10)C10—N1—C7—N2177.60 (10)
C6—C1—C2—C30.66 (18)C7—N2—C8—C997.94 (15)
N1—C1—C2—C3179.18 (12)C6—N2—C8—C977.49 (16)
C1—C2—C3—C40.7 (2)N2—C8—C9—O21.66 (19)
C2—C3—C4—C50.8 (2)N2—C8—C9—O1178.11 (12)
C3—C4—C5—C60.4 (2)C7—N1—C10—C11117.39 (13)
C7—N2—C6—C5179.40 (14)C1—N1—C10—C1165.06 (15)
C8—N2—C6—C54.5 (2)Mn1—O3—C11—O4161.23 (11)
C7—N2—C6—C10.43 (13)Mn1—O3—C11—C1020.1 (2)
C8—N2—C6—C1175.66 (11)N1—C10—C11—O410.15 (17)
C4—C5—C6—N2178.50 (13)N1—C10—C11—O3168.58 (11)
C4—C5—C6—C11.7 (2)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H6W···O20.83 (1)1.95 (1)2.7582 (15)165 (2)
O7—H5W···O40.84 (1)1.99 (1)2.7796 (14)157 (2)
O5—H2W···O2ii0.84 (1)1.84 (1)2.6767 (15)174 (2)
O6—H4W···O1iii0.84 (1)2.01 (1)2.8361 (14)169 (2)
O6—H3W···O3iv0.84 (1)1.93 (1)2.7574 (13)170 (2)
O5—H1W···O1v0.83 (1)2.01 (1)2.8255 (14)166 (2)
Symmetry codes: (ii) x+3/2, y1/2, z+1/2; (iii) x1/2, y+3/2, z1/2; (iv) x1, y, z; (v) x+1/2, y1/2, z+1/2.
 

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