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The crystal structure of the title compound, [Mn(ClCH2COO)(phen)2(H2O)]ClO4 (phen is 1,10-phenanthroline, C12H8N2), contains monomeric [Mn(ClCH2COO)(phen)2(H2O)]+ cations and perchlorate anions. The man­ganese ion is coordinated by two chelating phen ligands [Mn—N 2.243 (3)-2.375 (4) Å], one water mol­ecule [Mn—O 2.182 (3) Å] and a chloro­acetate ligand [Mn—O 2.119 (3) Å] in a distorted octahedral geometry. Consolidation of the crystal structure is achieved by O—H...O hydrogen-bonding interactions between the coordinated water mol­ecules and the uncoordinated O atom of the chloro­acetate ligand.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802010899/wn6101sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802010899/wn6101Isup2.hkl
Contains datablock I

CCDC reference: 189874

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.055
  • wR factor = 0.161
  • Data-to-parameter ratio = 12.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_731 Alert C Bond Calc 0.84(5), Rep 0.84(2) .... 2.50 s.u-Ratio O1 -H1C 1.555 1.555
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1994); data reduction: XPREP in SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Aqua(chloroacetato)bis(1,10-phenanthroline-N,N')manganese(II) perchlorate top
Crystal data top
[Mn(C2H2ClO2)(C12H8N2)2(H2O)]ClO4Z = 2
Mr = 626.30F(000) = 638
Triclinic, P1Dx = 1.618 Mg m3
a = 9.4884 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.6935 (5) ÅCell parameters from 3298 reflections
c = 15.2244 (8) Åθ = 1.4–25.1°
α = 74.715 (2)°µ = 0.78 mm1
β = 78.456 (1)°T = 293 K
γ = 73.955 (1)°Block, yellow–green
V = 1285.84 (11) Å30.70 × 0.24 × 0.20 mm
Data collection top
Siemens SMART CCD
diffractometer
4509 independent reflections
Radiation source: fine-focus sealed tube3229 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scansθmax = 25.1°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.615, Tmax = 0.856k = 117
6697 measured reflectionsl = 1618
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
4509 reflections(Δ/σ)max < 0.001
369 parametersΔρmax = 0.60 e Å3
1 restraintΔρmin = 0.73 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
Mn0.08530 (7)0.04280 (6)0.20919 (4)0.0417 (2)
O10.0912 (4)0.0224 (4)0.1695 (3)0.0535 (8)
H1B0.094 (6)0.035 (6)0.114 (4)0.071 (17)*
H1C0.127 (6)0.089 (5)0.206 (3)0.09 (2)*
O20.2535 (3)0.0612 (3)0.1171 (2)0.0532 (8)
O30.1359 (4)0.0548 (4)0.0036 (2)0.0624 (9)
O40.3465 (7)0.1912 (7)0.7630 (4)0.172 (3)
O50.3220 (7)0.4270 (6)0.6904 (4)0.137 (2)
O60.1546 (5)0.3064 (7)0.6810 (4)0.1212 (18)
O70.3937 (5)0.2548 (7)0.6054 (3)0.1171 (17)
N10.0848 (4)0.0710 (4)0.3444 (2)0.0492 (9)
N20.1559 (4)0.1507 (4)0.3236 (2)0.0453 (8)
N30.0112 (4)0.2811 (4)0.1514 (2)0.0469 (9)
N40.2510 (4)0.1693 (4)0.2157 (2)0.0447 (8)
C10.2003 (5)0.1820 (6)0.3571 (4)0.0613 (13)
H1A0.20790.27030.31340.074*
C20.3109 (6)0.1723 (7)0.4329 (4)0.0724 (16)
H2A0.38930.25280.44000.087*
C30.3012 (6)0.0429 (8)0.4958 (4)0.0725 (16)
H3A0.37620.03340.54510.087*
C40.1817 (6)0.0750 (6)0.4878 (3)0.0596 (13)
C50.1592 (7)0.2140 (8)0.5535 (3)0.0746 (17)
H5A0.23280.23050.60280.089*
C60.0363 (7)0.3193 (7)0.5457 (3)0.0738 (16)
H6A0.02350.40540.59120.089*
C70.0758 (6)0.3031 (5)0.4691 (3)0.0569 (12)
C80.2082 (7)0.4091 (6)0.4581 (4)0.0675 (14)
H8A0.22600.49650.50220.081*
C90.3103 (6)0.3851 (5)0.3836 (4)0.0669 (14)
H9A0.39950.45440.37690.080*
C100.2803 (5)0.2551 (5)0.3168 (3)0.0536 (11)
H10A0.35050.24050.26520.064*
C110.0558 (5)0.1718 (5)0.3996 (3)0.0457 (10)
C120.0730 (5)0.0556 (5)0.4101 (3)0.0477 (11)
C130.1396 (5)0.3362 (5)0.1187 (3)0.0584 (12)
H13A0.19280.27080.11530.070*
C140.1992 (6)0.4851 (6)0.0894 (4)0.0683 (14)
H14A0.29050.51810.06800.082*
C150.1221 (7)0.5823 (6)0.0924 (4)0.0725 (16)
H15A0.16020.68290.07270.087*
C160.0165 (6)0.5300 (5)0.1256 (3)0.0605 (13)
C170.1080 (8)0.6233 (6)0.1277 (4)0.0802 (18)
H17A0.07450.72470.10880.096*
C180.2395 (8)0.5686 (6)0.1558 (4)0.0777 (17)
H18A0.29710.63250.15520.093*
C190.2959 (6)0.4130 (6)0.1873 (3)0.0613 (13)
C200.4342 (6)0.3482 (7)0.2168 (4)0.0721 (16)
H19A0.49600.40700.21820.086*
C210.4787 (6)0.1999 (7)0.2434 (4)0.0682 (14)
H20A0.57100.15670.26280.082*
C220.3846 (5)0.1118 (6)0.2413 (3)0.0532 (11)
H21A0.41690.01000.25850.064*
C230.2075 (5)0.3174 (5)0.1873 (3)0.0473 (11)
C240.0659 (5)0.3784 (4)0.1546 (3)0.0471 (10)
C250.3697 (5)0.0930 (6)0.0328 (4)0.0634 (13)
H25A0.40830.01290.07420.076*
H25B0.33100.13800.06970.076*
C260.2428 (5)0.0285 (4)0.0329 (3)0.0442 (10)
Cl10.51505 (18)0.22189 (19)0.01526 (13)0.1000 (6)
Cl20.30539 (13)0.29146 (14)0.68438 (9)0.0637 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn0.0448 (4)0.0290 (3)0.0477 (4)0.0076 (3)0.0059 (3)0.0043 (3)
O10.058 (2)0.056 (2)0.051 (2)0.0212 (16)0.0059 (16)0.0131 (17)
O20.0586 (19)0.0505 (18)0.0487 (18)0.0081 (15)0.0056 (14)0.0140 (15)
O30.0540 (19)0.059 (2)0.064 (2)0.0002 (17)0.0081 (16)0.0098 (17)
O40.139 (5)0.159 (6)0.114 (4)0.043 (4)0.009 (4)0.055 (4)
O50.151 (5)0.111 (4)0.165 (5)0.068 (4)0.039 (4)0.064 (4)
O60.061 (3)0.171 (5)0.133 (4)0.022 (3)0.011 (3)0.045 (4)
O70.098 (3)0.149 (5)0.108 (4)0.027 (3)0.021 (3)0.064 (3)
N10.048 (2)0.050 (2)0.052 (2)0.0094 (18)0.0050 (17)0.0182 (18)
N20.052 (2)0.040 (2)0.044 (2)0.0139 (17)0.0075 (16)0.0048 (16)
N30.051 (2)0.0320 (18)0.052 (2)0.0078 (16)0.0043 (17)0.0036 (16)
N40.047 (2)0.043 (2)0.046 (2)0.0160 (16)0.0019 (16)0.0143 (16)
C10.057 (3)0.066 (3)0.065 (3)0.008 (3)0.011 (2)0.026 (3)
C20.051 (3)0.097 (5)0.074 (4)0.003 (3)0.002 (3)0.046 (4)
C30.069 (4)0.109 (5)0.050 (3)0.032 (3)0.006 (3)0.034 (3)
C40.061 (3)0.084 (4)0.046 (3)0.031 (3)0.002 (2)0.027 (3)
C50.092 (4)0.103 (5)0.040 (3)0.056 (4)0.009 (3)0.013 (3)
C60.098 (5)0.087 (4)0.044 (3)0.048 (4)0.006 (3)0.002 (3)
C70.078 (3)0.055 (3)0.044 (3)0.031 (3)0.014 (2)0.002 (2)
C80.092 (4)0.048 (3)0.062 (3)0.023 (3)0.029 (3)0.008 (2)
C90.077 (4)0.045 (3)0.074 (4)0.007 (3)0.028 (3)0.000 (3)
C100.059 (3)0.042 (3)0.055 (3)0.009 (2)0.010 (2)0.004 (2)
C110.056 (3)0.048 (3)0.039 (2)0.022 (2)0.009 (2)0.0066 (19)
C120.054 (3)0.061 (3)0.038 (2)0.028 (2)0.0046 (19)0.014 (2)
C130.057 (3)0.044 (3)0.067 (3)0.006 (2)0.010 (2)0.006 (2)
C140.064 (3)0.049 (3)0.073 (3)0.006 (3)0.008 (3)0.003 (3)
C150.084 (4)0.033 (3)0.074 (4)0.010 (3)0.007 (3)0.005 (2)
C160.081 (4)0.034 (2)0.056 (3)0.013 (2)0.018 (3)0.014 (2)
C170.112 (5)0.039 (3)0.088 (4)0.027 (3)0.016 (4)0.022 (3)
C180.110 (5)0.056 (3)0.080 (4)0.050 (4)0.018 (4)0.029 (3)
C190.071 (3)0.061 (3)0.061 (3)0.035 (3)0.017 (3)0.029 (3)
C200.070 (4)0.096 (5)0.070 (3)0.048 (3)0.013 (3)0.039 (3)
C210.054 (3)0.095 (5)0.064 (3)0.025 (3)0.000 (2)0.031 (3)
C220.048 (3)0.057 (3)0.056 (3)0.012 (2)0.001 (2)0.019 (2)
C230.060 (3)0.042 (2)0.043 (2)0.023 (2)0.011 (2)0.0153 (19)
C240.059 (3)0.034 (2)0.044 (2)0.013 (2)0.008 (2)0.0114 (19)
C250.056 (3)0.070 (3)0.065 (3)0.003 (3)0.009 (2)0.029 (3)
C260.048 (3)0.033 (2)0.053 (3)0.012 (2)0.003 (2)0.0118 (19)
Cl10.0707 (10)0.0807 (11)0.1137 (13)0.0112 (8)0.0033 (9)0.0000 (9)
Cl20.0574 (7)0.0595 (8)0.0609 (7)0.0106 (6)0.0037 (6)0.0024 (6)
Geometric parameters (Å, º) top
Mn—O22.119 (3)C6—H6A0.9300
Mn—O12.182 (3)C7—C81.398 (7)
Mn—N32.243 (3)C7—C111.418 (6)
Mn—N22.248 (3)C8—C91.351 (8)
Mn—N42.275 (3)C8—H8A0.9300
Mn—N12.375 (4)C9—C101.394 (6)
O1—H1B0.89 (5)C9—H9A0.9300
O1—H1C0.84 (2)C10—H10A0.9300
O2—C261.255 (5)C11—C121.429 (6)
O3—C261.235 (5)C13—C141.383 (7)
O4—Cl21.376 (5)C13—H13A0.9300
O5—Cl21.394 (5)C14—C151.357 (8)
O6—Cl21.408 (4)C14—H14A0.9300
O7—Cl21.390 (4)C15—C161.417 (8)
N1—C11.330 (6)C15—H15A0.9300
N1—C121.357 (6)C16—C241.390 (6)
N2—C101.332 (6)C16—C171.425 (8)
N2—C111.351 (5)C17—C181.324 (8)
N3—C131.326 (6)C17—H17A0.9300
N3—C241.360 (5)C18—C191.437 (8)
N4—C221.328 (6)C18—H18A0.9300
N4—C231.355 (5)C19—C201.397 (8)
C1—C21.398 (7)C19—C231.411 (6)
C1—H1A0.9300C20—C211.354 (8)
C2—C31.355 (8)C20—H19A0.9300
C2—H2A0.9300C21—C221.405 (7)
C3—C41.382 (8)C21—H20A0.9300
C3—H3A0.9300C22—H21A0.9300
C4—C121.415 (6)C23—C241.441 (6)
C4—C51.442 (8)C25—C261.507 (6)
C5—C61.329 (8)C25—Cl11.723 (5)
C5—H5A0.9300C25—H25A0.9700
C6—C71.419 (7)C25—H25B0.9700
O2—Mn—O194.08 (13)N2—C10—H10A118.5
O2—Mn—N3113.93 (12)C9—C10—H10A118.5
O1—Mn—N391.41 (13)N2—C11—C7122.3 (4)
O2—Mn—N288.77 (13)N2—C11—C12118.1 (4)
O1—Mn—N2100.51 (13)C7—C11—C12119.6 (4)
N3—Mn—N2153.65 (13)N1—C12—C4122.5 (5)
O2—Mn—N485.87 (12)N1—C12—C11117.9 (4)
O1—Mn—N4162.90 (13)C4—C12—C11119.7 (4)
N3—Mn—N473.13 (13)N3—C13—C14124.0 (5)
N2—Mn—N496.59 (13)N3—C13—H13A118.0
O2—Mn—N1159.23 (13)C14—C13—H13A118.0
O1—Mn—N183.81 (13)C15—C14—C13118.9 (5)
N3—Mn—N186.81 (13)C15—C14—H14A120.5
N2—Mn—N171.41 (13)C13—C14—H14A120.5
N4—Mn—N1102.14 (12)C14—C15—C16119.7 (5)
Mn—O1—H1B126 (3)C14—C15—H15A120.1
Mn—O1—H1C118 (4)C16—C15—H15A120.1
H1B—O1—H1C104 (5)C24—C16—C15117.0 (5)
C26—O2—Mn119.9 (3)C24—C16—C17119.3 (5)
C1—N1—C12117.7 (4)C15—C16—C17123.6 (5)
C1—N1—Mn128.9 (3)C18—C17—C16121.3 (5)
C12—N1—Mn112.4 (3)C18—C17—H17A119.3
C10—N2—C11118.0 (4)C16—C17—H17A119.3
C10—N2—Mn124.4 (3)C17—C18—C19121.8 (5)
C11—N2—Mn116.9 (3)C17—C18—H18A119.1
C13—N3—C24117.2 (4)C19—C18—H18A119.1
C13—N3—Mn126.1 (3)C20—C19—C23116.9 (5)
C24—N3—Mn116.6 (3)C20—C19—C18124.6 (5)
C22—N4—C23118.4 (4)C23—C19—C18118.4 (5)
C22—N4—Mn126.5 (3)C21—C20—C19120.2 (5)
C23—N4—Mn115.1 (3)C21—C20—H19A119.9
N1—C1—C2123.2 (5)C19—C20—H19A119.9
N1—C1—H1A118.4C20—C21—C22119.5 (5)
C2—C1—H1A118.4C20—C21—H20A120.2
C3—C2—C1118.4 (5)C22—C21—H20A120.2
C3—C2—H2A120.8N4—C22—C21122.1 (5)
C1—C2—H2A120.8N4—C22—H21A118.9
C2—C3—C4121.1 (5)C21—C22—H21A118.9
C2—C3—H3A119.5N4—C23—C19122.8 (5)
C4—C3—H3A119.5N4—C23—C24118.1 (4)
C3—C4—C12117.1 (5)C19—C23—C24119.2 (4)
C3—C4—C5124.7 (5)N3—C24—C16123.2 (5)
C12—C4—C5118.2 (5)N3—C24—C23116.8 (4)
C6—C5—C4121.9 (5)C16—C24—C23119.9 (4)
C6—C5—H5A119.1C26—C25—Cl1116.7 (4)
C4—C5—H5A119.1C26—C25—H25A108.1
C5—C6—C7121.3 (5)Cl1—C25—H25A108.1
C5—C6—H6A119.3C26—C25—H25B108.1
C7—C6—H6A119.3Cl1—C25—H25B108.1
C8—C7—C11117.0 (4)H25A—C25—H25B107.3
C8—C7—C6123.8 (5)O3—C26—O2126.1 (4)
C11—C7—C6119.2 (5)O3—C26—C25114.7 (4)
C9—C8—C7120.3 (5)O2—C26—C25119.2 (4)
C9—C8—H8A119.8O4—Cl2—O7112.4 (4)
C7—C8—H8A119.8O4—Cl2—O5107.3 (5)
C8—C9—C10119.1 (5)O7—Cl2—O5108.2 (3)
C8—C9—H9A120.4O4—Cl2—O6109.6 (4)
C10—C9—H9A120.4O7—Cl2—O6111.6 (3)
N2—C10—C9123.0 (5)O5—Cl2—O6107.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···O3i0.89 (5)1.87 (6)2.753 (5)170 (5)
Symmetry code: (i) x, y, z.
 

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