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Reactions of manganese(II) chloride, bromide and iodide with proline as an enantiopure and racemic ligand result in six crystalline solids for which diffraction experiments have been performed at 100 K. For two of these compounds, crystal structures at ambient temperature had been reported previously. The most surprising outcome of our systematic comparison lies in the role of chirality: with enantiopure proline three different coordination polymers have been obtained, whereas racemic proline yields isomorphous mononuclear complexes under the same reaction conditions.

Supporting information

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Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768112043996/gp5056sup1.cif
Contains datablocks 1a, 1b, 1c, 2a, 2b, 2c, global

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Contains datablock 1a

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Structure factor file (CIF format) https://doi.org/10.1107/S0108768112043996/gp50561csup4.hkl
Contains datablock 1c

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Contains datablock 2a

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Powder diffractograms

CCDC references: 914848; 914849; 914850; 914851; 914852; 914853

Computing details top

For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
(1a) top
Crystal data top
C5H9Cl2MnNO2·H2OF(000) = 524
Mr = 258.99Dx = 1.829 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1584 reflections
a = 7.0862 (6) Åθ = 2.6–21.4°
b = 10.0235 (8) ŵ = 1.94 mm1
c = 13.2437 (11) ÅT = 100 K
V = 940.68 (13) Å30.14 × 0.06 × 0.05 mm
Z = 4
Data collection top
Bruker D8 goniometer with SMART APEX CCD detector
diffractometer
2039 independent reflections
Radiation source: microsource1797 reflections with I > 2σ(I)
Multi layer optics monochromatorRint = 0.058
ω scansθmax = 27.1°, θmin = 2.6°
Absorption correction: multi-scan
SADABS
h = 88
Tmin = 0.773, Tmax = 0.909k = 1212
11373 measured reflectionsl = 1616
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.074 w = 1/[σ2(Fo2) + (0.035P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
2039 reflectionsΔρmax = 0.52 e Å3
121 parametersΔρmin = 0.33 e Å3
4 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (4)
Crystal data top
C5H9Cl2MnNO2·H2OV = 940.68 (13) Å3
Mr = 258.99Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.0862 (6) ŵ = 1.94 mm1
b = 10.0235 (8) ÅT = 100 K
c = 13.2437 (11) Å0.14 × 0.06 × 0.05 mm
Data collection top
Bruker D8 goniometer with SMART APEX CCD detector
diffractometer
2039 independent reflections
Absorption correction: multi-scan
SADABS
1797 reflections with I > 2σ(I)
Tmin = 0.773, Tmax = 0.909Rint = 0.058
11373 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.074Δρmax = 0.52 e Å3
S = 1.06Δρmin = 0.33 e Å3
2039 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
121 parametersAbsolute structure parameter: 0.02 (4)
4 restraints
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
Mn10.32439 (6)0.24773 (5)0.50034 (4)0.01702 (13)
Cl10.57461 (12)0.36706 (8)0.60399 (6)0.02109 (18)
Cl20.57519 (12)0.06994 (7)0.46770 (5)0.01899 (17)
O10.4195 (3)0.3579 (2)0.37232 (15)0.0220 (5)
O20.7347 (3)0.3581 (2)0.36705 (16)0.0207 (5)
C10.5733 (5)0.4069 (3)0.3492 (2)0.0176 (6)
C20.5742 (5)0.5406 (3)0.2945 (2)0.0249 (7)
H20.64770.53510.23020.030*
C30.6488 (6)0.6513 (4)0.3617 (4)0.0408 (11)
H3A0.75520.61940.40370.049*
H3B0.69140.72850.32110.049*
C40.4804 (6)0.6881 (4)0.4268 (3)0.0464 (12)
H4A0.49380.77960.45390.056*
H4B0.46670.62500.48390.056*
C50.3123 (6)0.6788 (4)0.3561 (3)0.0342 (10)
H5A0.19970.64520.39220.041*
H5B0.28260.76720.32670.041*
N10.3728 (4)0.5818 (3)0.2746 (2)0.0230 (7)
H1A0.285 (4)0.516 (3)0.281 (3)0.028*
H1B0.363 (5)0.619 (3)0.2126 (17)0.028*
O30.0825 (4)0.4035 (3)0.2380 (2)0.0392 (7)
H1O0.015 (5)0.377 (4)0.290 (2)0.047*
H2O0.006 (5)0.452 (4)0.199 (3)0.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0132 (2)0.0212 (2)0.0166 (2)0.00012 (18)0.00084 (17)0.0030 (2)
Cl10.0158 (4)0.0258 (4)0.0217 (4)0.0012 (4)0.0014 (4)0.0042 (3)
Cl20.0160 (4)0.0192 (3)0.0218 (4)0.0001 (4)0.0001 (4)0.0008 (3)
O10.0185 (12)0.0269 (12)0.0207 (12)0.0026 (12)0.0009 (12)0.0105 (10)
O20.0149 (12)0.0285 (13)0.0186 (13)0.0022 (11)0.0011 (10)0.0067 (11)
C10.0194 (16)0.0213 (16)0.0119 (14)0.0011 (16)0.0010 (15)0.0002 (12)
C20.0173 (16)0.0300 (18)0.0274 (18)0.0032 (18)0.0007 (17)0.0114 (14)
C30.038 (2)0.027 (2)0.058 (3)0.0076 (18)0.014 (2)0.007 (2)
C40.078 (4)0.024 (2)0.037 (2)0.001 (2)0.013 (2)0.0044 (18)
C50.047 (3)0.027 (2)0.028 (2)0.0081 (19)0.0118 (19)0.0036 (17)
N10.0246 (17)0.0249 (16)0.0193 (15)0.0049 (13)0.0008 (12)0.0058 (13)
O30.0346 (16)0.0481 (17)0.0349 (15)0.0014 (17)0.0006 (15)0.0179 (13)
Geometric parameters (Å, º) top
Mn1—O12.133 (2)C2—H21.0000
Mn1—O2i2.148 (2)C3—C41.517 (6)
Mn1—Cl1i2.5231 (9)C3—H3A0.9900
Mn1—Cl12.5414 (10)C3—H3B0.9900
Mn1—Cl22.5536 (9)C4—C51.518 (5)
Mn1—Cl2i2.5764 (9)C4—H4A0.9900
Cl1—Mn1ii2.5231 (9)C4—H4B0.9900
Cl2—Mn1ii2.5764 (9)C5—N11.514 (5)
O1—C11.234 (4)C5—H5A0.9900
O2—C11.266 (4)C5—H5B0.9900
O2—Mn1ii2.148 (2)N1—H1A0.906 (18)
C1—C21.523 (4)N1—H1B0.906 (18)
C2—N11.509 (4)O3—H1O0.878 (19)
C2—C31.517 (5)O3—H2O0.890 (18)
O1—Mn1—O2i177.78 (10)C1—C2—H2111.0
O1—Mn1—Cl1i91.29 (7)C4—C3—C2103.7 (3)
O2i—Mn1—Cl1i90.87 (6)C4—C3—H3A111.0
O1—Mn1—Cl188.00 (7)C2—C3—H3A111.0
O2i—Mn1—Cl189.83 (7)C4—C3—H3B111.0
Cl1i—Mn1—Cl1179.03 (3)C2—C3—H3B111.0
O1—Mn1—Cl290.39 (7)H3A—C3—H3B109.0
O2i—Mn1—Cl289.99 (7)C3—C4—C5104.6 (3)
Cl1i—Mn1—Cl294.43 (3)C3—C4—H4A110.8
Cl1—Mn1—Cl286.23 (3)C5—C4—H4A110.8
O1—Mn1—Cl2i88.84 (7)C3—C4—H4B110.8
O2i—Mn1—Cl2i90.75 (7)C5—C4—H4B110.8
Cl1i—Mn1—Cl2i86.13 (3)H4A—C4—H4B108.9
Cl1—Mn1—Cl2i93.19 (3)N1—C5—C4104.9 (3)
Cl2—Mn1—Cl2i179.06 (3)N1—C5—H5A110.8
Mn1ii—Cl1—Mn188.80 (2)C4—C5—H5A110.8
Mn1—Cl2—Mn1ii87.37 (2)N1—C5—H5B110.8
C1—O1—Mn1133.0 (2)C4—C5—H5B110.8
C1—O2—Mn1ii127.6 (2)H5A—C5—H5B108.8
O1—C1—O2126.7 (3)C2—N1—C5108.6 (3)
O1—C1—C2118.1 (3)C2—N1—H1A116 (3)
O2—C1—C2115.2 (3)C5—N1—H1A102 (3)
N1—C2—C3103.4 (3)C2—N1—H1B110 (2)
N1—C2—C1108.7 (3)C5—N1—H1B111 (2)
C3—C2—C1111.5 (3)H1A—N1—H1B109 (3)
N1—C2—H2111.0H1O—O3—H2O106 (4)
C3—C2—H2111.0
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x+1/2, y+1/2, z+1.
(1b) top
Crystal data top
C7H17Br2MnNO4F(000) = 386
Mr = 393.98Dx = 2.039 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1044 reflections
a = 8.286 (2) Åθ = 2.5–22.3°
b = 8.256 (2) ŵ = 7.25 mm1
c = 9.387 (3) ÅT = 100 K
β = 92.172 (4)°Needle, colorless
V = 641.7 (3) Å30.27 × 0.08 × 0.08 mm
Z = 2
Data collection top
Bruker D8 goniometer with SMART APEX CCD detector
diffractometer
2665 independent reflections
Radiation source: microsource2440 reflections with I > 2σ(I)
Multi layer optics monochromatorRint = 0.061
ω scansθmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan
SADABS
h = 1010
Tmin = 0.245, Tmax = 0.595k = 1010
7642 measured reflectionsl = 1111
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.064 w = 1/[σ2(Fo2) + (0.P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
2665 reflectionsΔρmax = 0.61 e Å3
152 parametersΔρmin = 0.48 e Å3
4 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.015 (12)
Crystal data top
C7H17Br2MnNO4V = 641.7 (3) Å3
Mr = 393.98Z = 2
Monoclinic, P21Mo Kα radiation
a = 8.286 (2) ŵ = 7.25 mm1
b = 8.256 (2) ÅT = 100 K
c = 9.387 (3) Å0.27 × 0.08 × 0.08 mm
β = 92.172 (4)°
Data collection top
Bruker D8 goniometer with SMART APEX CCD detector
diffractometer
2665 independent reflections
Absorption correction: multi-scan
SADABS
2440 reflections with I > 2σ(I)
Tmin = 0.245, Tmax = 0.595Rint = 0.061
7642 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.064Δρmax = 0.61 e Å3
S = 1.00Δρmin = 0.48 e Å3
2665 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
152 parametersAbsolute structure parameter: 0.015 (12)
4 restraints
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
Mn10.00733 (9)0.82303 (10)0.66340 (8)0.01330 (18)
Br10.10226 (6)0.84859 (6)0.92578 (5)0.01619 (13)
Br20.26334 (6)0.65186 (7)0.71320 (6)0.01977 (14)
O10.0888 (4)0.8426 (5)0.4355 (3)0.0164 (8)
O20.1196 (4)1.1077 (4)0.4017 (4)0.0154 (8)
C10.1209 (6)0.9616 (7)0.3596 (5)0.0144 (12)
C20.1742 (7)0.9361 (6)0.2035 (5)0.0136 (12)
H20.10170.99860.14090.016*
C30.3499 (7)0.9880 (7)0.1733 (6)0.0210 (13)
H3A0.41030.99120.26230.025*
H3B0.35531.09610.12770.025*
C40.4172 (6)0.8570 (7)0.0721 (5)0.0175 (11)
H4A0.53620.84970.07560.021*
H4B0.38720.87800.02730.021*
C50.3379 (7)0.7068 (7)0.1296 (6)0.0229 (14)
H5A0.34060.61950.05720.028*
H5B0.39150.66800.21570.028*
N10.1682 (6)0.7588 (5)0.1651 (5)0.0134 (10)
H1A0.105 (5)0.756 (7)0.085 (4)0.016*
H1B0.117 (5)0.702 (6)0.238 (4)0.016*
O30.2121 (5)0.9575 (5)0.5868 (4)0.0207 (9)
H30.207 (7)0.997 (7)0.508 (5)0.027 (19)*
C60.3698 (6)0.8857 (7)0.5969 (6)0.0220 (14)
H7A0.39530.85490.69600.033*
H7B0.44990.96390.56530.033*
H7C0.37180.78920.53620.033*
O40.0991 (5)1.0725 (5)0.6809 (4)0.0174 (9)
H40.111 (7)1.085 (8)0.595 (5)0.026 (19)*
C70.2383 (6)1.1217 (8)0.7557 (6)0.0230 (14)
H6A0.33281.06060.71990.035*
H6B0.25711.23780.74070.035*
H6C0.22041.10040.85780.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0166 (4)0.0108 (5)0.0124 (4)0.0003 (4)0.0001 (3)0.0000 (3)
Br10.0215 (3)0.0145 (3)0.0124 (2)0.0014 (3)0.0001 (2)0.0005 (2)
Br20.0182 (3)0.0191 (3)0.0224 (3)0.0047 (3)0.0047 (2)0.0030 (3)
O10.0213 (19)0.0117 (19)0.0162 (17)0.0005 (19)0.0013 (14)0.0020 (19)
O20.023 (2)0.008 (2)0.0156 (19)0.0021 (16)0.0014 (16)0.0005 (15)
C10.012 (3)0.018 (3)0.014 (3)0.002 (2)0.004 (2)0.000 (2)
C20.018 (3)0.008 (3)0.014 (3)0.003 (2)0.003 (2)0.003 (2)
C30.020 (3)0.018 (3)0.024 (3)0.007 (3)0.005 (2)0.003 (3)
C40.015 (3)0.018 (3)0.019 (3)0.003 (3)0.003 (2)0.004 (3)
C50.016 (3)0.021 (3)0.032 (3)0.006 (2)0.003 (3)0.001 (3)
N10.016 (3)0.010 (2)0.015 (2)0.0000 (19)0.0022 (19)0.0027 (19)
O30.019 (2)0.021 (2)0.023 (2)0.0008 (18)0.0029 (18)0.0104 (19)
C60.013 (3)0.025 (4)0.028 (3)0.002 (2)0.001 (2)0.002 (3)
O40.024 (2)0.014 (2)0.013 (2)0.0039 (17)0.0045 (17)0.0018 (17)
C70.021 (3)0.024 (4)0.024 (3)0.003 (3)0.006 (2)0.003 (3)
Geometric parameters (Å, º) top
Mn1—O2i2.165 (3)C4—H4A0.9900
Mn1—O42.204 (4)C4—H4B0.9900
Mn1—O12.225 (3)C5—N11.496 (7)
Mn1—O32.270 (4)C5—H5A0.9900
Mn1—Br12.6011 (11)C5—H5B0.9900
Mn1—Br22.6060 (11)N1—H1A0.931 (19)
O1—C11.237 (6)N1—H1B0.924 (19)
O2—C11.269 (6)O3—C61.435 (6)
O2—Mn1ii2.165 (3)O3—H30.81 (4)
C1—C21.529 (7)C6—H7A0.9800
C2—N11.509 (6)C6—H7B0.9800
C2—C31.534 (7)C6—H7C0.9800
C2—H21.0000O4—C71.432 (6)
C3—C41.531 (8)O4—H40.82 (4)
C3—H3A0.9900C7—H6A0.9800
C3—H3B0.9900C7—H6B0.9800
C4—C51.494 (8)C7—H6C0.9800
O2i—Mn1—O4163.94 (14)C3—C4—H4A111.3
O2i—Mn1—O185.49 (14)C5—C4—H4B111.3
O4—Mn1—O184.87 (14)C3—C4—H4B111.3
O2i—Mn1—O384.76 (14)H4A—C4—H4B109.2
O4—Mn1—O381.34 (14)C4—C5—N1103.8 (4)
O1—Mn1—O382.96 (14)C4—C5—H5A111.0
O2i—Mn1—Br1100.25 (10)N1—C5—H5A111.0
O4—Mn1—Br187.86 (10)C4—C5—H5B111.0
O1—Mn1—Br1170.74 (11)N1—C5—H5B111.0
O3—Mn1—Br190.29 (11)H5A—C5—H5B109.0
O2i—Mn1—Br290.73 (10)C5—N1—C2107.0 (4)
O4—Mn1—Br2102.00 (11)C5—N1—H1A112 (3)
O1—Mn1—Br289.57 (10)C2—N1—H1A104 (3)
O3—Mn1—Br2171.54 (11)C5—N1—H1B115 (3)
Br1—Mn1—Br297.56 (3)C2—N1—H1B110 (3)
C1—O1—Mn1131.5 (3)H1A—N1—H1B109 (4)
C1—O2—Mn1ii133.7 (3)C6—O3—Mn1121.0 (3)
O1—C1—O2125.2 (5)C6—O3—H3104 (4)
O1—C1—C2119.4 (5)Mn1—O3—H3118 (4)
O2—C1—C2115.4 (5)O3—C6—H7A109.5
N1—C2—C1110.6 (4)O3—C6—H7B109.5
N1—C2—C3105.5 (4)H7A—C6—H7B109.5
C1—C2—C3112.1 (4)O3—C6—H7C109.5
N1—C2—H2109.5H7A—C6—H7C109.5
C1—C2—H2109.5H7B—C6—H7C109.5
C3—C2—H2109.5C7—O4—Mn1126.1 (3)
C4—C3—C2103.8 (4)C7—O4—H4112 (4)
C4—C3—H3A111.0Mn1—O4—H494 (4)
C2—C3—H3A111.0O4—C7—H6A109.5
C4—C3—H3B111.0O4—C7—H6B109.5
C2—C3—H3B111.0H6A—C7—H6B109.5
H3A—C3—H3B109.0O4—C7—H6C109.5
C5—C4—C3102.6 (4)H6A—C7—H6C109.5
C5—C4—H4A111.3H6B—C7—H6C109.5
Symmetry codes: (i) x, y1/2, z+1; (ii) x, y+1/2, z+1.
(1c) top
Crystal data top
C5H15IMnNO5·IF(000) = 892
Mr = 477.92Dx = 2.398 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1755 reflections
a = 8.1264 (18) Åθ = 2.3–25.5°
b = 11.867 (3) ŵ = 5.66 mm1
c = 13.727 (3) ÅT = 100 K
V = 1323.8 (5) Å3Needle, orange
Z = 40.14 × 0.08 × 0.08 mm
Data collection top
Bruker D8 goniometer with SMART APEX CCD detector
diffractometer
2690 independent reflections
Radiation source: microsource2412 reflections with I > 2σ(I)
Multi layer optics monochromatorRint = 0.086
ω scansθmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan
SADABS
h = 1010
Tmin = 0.505, Tmax = 0.660k = 1414
15709 measured reflectionsl = 1717
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.078 w = 1/[σ2(Fo2) + (0.030P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
2690 reflectionsΔρmax = 1.13 e Å3
151 parametersΔρmin = 1.09 e Å3
21 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (5)
Crystal data top
C5H15IMnNO5·IV = 1323.8 (5) Å3
Mr = 477.92Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.1264 (18) ŵ = 5.66 mm1
b = 11.867 (3) ÅT = 100 K
c = 13.727 (3) Å0.14 × 0.08 × 0.08 mm
Data collection top
Bruker D8 goniometer with SMART APEX CCD detector
diffractometer
2690 independent reflections
Absorption correction: multi-scan
SADABS
2412 reflections with I > 2σ(I)
Tmin = 0.505, Tmax = 0.660Rint = 0.086
15709 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.078Δρmax = 1.13 e Å3
S = 1.03Δρmin = 1.09 e Å3
2690 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
151 parametersAbsolute structure parameter: 0.05 (5)
21 restraints
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
Mn10.46947 (13)0.16430 (8)0.57996 (7)0.0135 (2)
I10.47616 (5)0.03518 (3)0.69319 (3)0.01778 (12)
O10.4834 (6)0.3317 (3)0.5121 (3)0.0158 (10)
O20.7527 (6)0.3675 (4)0.5025 (3)0.0164 (11)
C10.6035 (8)0.3912 (6)0.4892 (4)0.0095 (12)
C20.5693 (8)0.5042 (5)0.4401 (5)0.0147 (12)
H20.62580.50750.37540.018*
C30.6178 (9)0.6069 (6)0.5021 (5)0.0187 (13)
H3A0.69900.58540.55250.022*
H3B0.66580.66690.46080.022*
C40.4586 (9)0.6466 (6)0.5486 (5)0.0212 (14)
H4A0.46530.72710.56710.025*
H4B0.43180.60140.60700.025*
C50.3327 (9)0.6283 (6)0.4685 (6)0.0198 (14)
H5A0.21970.62420.49530.024*
H5B0.33780.68890.41910.024*
N10.3856 (7)0.5171 (5)0.4267 (4)0.0156 (11)
H1A0.348 (8)0.517 (7)0.363 (2)0.019*
H1B0.331 (8)0.465 (5)0.463 (4)0.019*
O30.6187 (6)0.1028 (4)0.4573 (4)0.0183 (11)
H6A0.572 (8)0.056 (5)0.420 (4)0.022*
H6B0.661 (9)0.148 (5)0.417 (4)0.022*
O40.6893 (7)0.2186 (5)0.6499 (4)0.0206 (12)
H7A0.733 (9)0.270 (5)0.618 (5)0.025*
H7B0.740 (8)0.198 (6)0.700 (3)0.025*
O50.2999 (6)0.2602 (4)0.6791 (4)0.0156 (10)
H8A0.317 (9)0.312 (4)0.720 (4)0.019*
H8B0.236 (7)0.226 (6)0.717 (4)0.019*
I21.01186 (5)0.61933 (3)0.69342 (3)0.01725 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0126 (5)0.0105 (5)0.0174 (5)0.0006 (4)0.0010 (4)0.0009 (4)
I10.0179 (2)0.0130 (2)0.0224 (2)0.00079 (17)0.0012 (2)0.00490 (18)
O10.014 (2)0.010 (2)0.024 (2)0.002 (2)0.002 (2)0.0058 (18)
O20.013 (2)0.015 (3)0.022 (3)0.002 (2)0.001 (2)0.001 (2)
C10.014 (3)0.007 (2)0.008 (3)0.001 (2)0.002 (2)0.004 (2)
C20.015 (2)0.011 (2)0.018 (3)0.000 (2)0.002 (3)0.0017 (17)
C30.021 (2)0.005 (2)0.029 (4)0.003 (2)0.006 (2)0.001 (3)
C40.026 (3)0.010 (3)0.027 (4)0.004 (3)0.003 (2)0.002 (2)
C50.021 (3)0.008 (3)0.031 (4)0.004 (2)0.003 (3)0.004 (3)
N10.015 (2)0.012 (3)0.020 (3)0.0007 (19)0.001 (2)0.002 (2)
O30.021 (3)0.012 (3)0.022 (3)0.005 (2)0.001 (2)0.003 (2)
O40.021 (3)0.018 (3)0.022 (3)0.002 (2)0.005 (2)0.008 (2)
O50.021 (3)0.009 (3)0.017 (3)0.002 (2)0.004 (2)0.001 (2)
I20.0165 (2)0.0185 (2)0.0167 (2)0.00217 (18)0.0009 (2)0.00241 (18)
Geometric parameters (Å, º) top
Mn1—O2i2.127 (5)C3—H3B0.9900
Mn1—O42.128 (6)C4—C51.517 (10)
Mn1—O12.197 (4)C4—H4A0.9900
Mn1—O32.200 (5)C4—H4B0.9900
Mn1—O52.246 (5)C5—N11.502 (9)
Mn1—I12.8323 (11)C5—H5A0.9900
O1—C11.245 (7)C5—H5B0.9900
O2—C11.258 (8)N1—H1A0.92 (2)
O2—Mn1ii2.127 (5)N1—H1B0.91 (2)
C1—C21.527 (9)O3—H6A0.84 (2)
C2—N11.512 (9)O3—H6B0.84 (2)
C2—C31.538 (9)O4—H7A0.83 (2)
C2—H21.0000O4—H7B0.84 (2)
C3—C41.517 (10)O5—H8A0.84 (2)
C3—H3A0.9900O5—H8B0.84 (2)
O2i—Mn1—O4171.42 (19)C2—C3—H3B110.7
O2i—Mn1—O188.70 (18)H3A—C3—H3B108.8
O4—Mn1—O182.79 (18)C3—C4—C5103.1 (6)
O2i—Mn1—O389.47 (19)C3—C4—H4A111.2
O4—Mn1—O389.0 (2)C5—C4—H4A111.2
O1—Mn1—O386.97 (18)C3—C4—H4B111.2
O2i—Mn1—O584.48 (18)C5—C4—H4B111.2
O4—Mn1—O595.1 (2)H4A—C4—H4B109.1
O1—Mn1—O580.24 (17)N1—C5—C4102.1 (5)
O3—Mn1—O5165.95 (19)N1—C5—H5A111.3
O2i—Mn1—I199.19 (13)C4—C5—H5A111.3
O4—Mn1—I189.38 (14)N1—C5—H5B111.3
O1—Mn1—I1170.89 (12)C4—C5—H5B111.3
O3—Mn1—I197.59 (14)H5A—C5—H5B109.2
O5—Mn1—I195.90 (13)C5—N1—C2109.0 (6)
C1—O1—Mn1131.3 (4)C5—N1—H1A105 (5)
C1—O2—Mn1ii139.5 (4)C2—N1—H1A116 (5)
O1—C1—O2126.3 (6)C5—N1—H1B104 (5)
O1—C1—C2117.9 (6)C2—N1—H1B110 (5)
O2—C1—C2115.8 (6)H1A—N1—H1B111 (7)
N1—C2—C1108.8 (5)Mn1—O3—H6A116 (5)
N1—C2—C3103.9 (6)Mn1—O3—H6B121 (5)
C1—C2—C3113.9 (5)H6A—O3—H6B102 (7)
N1—C2—H2110.0Mn1—O4—H7A110 (6)
C1—C2—H2110.0Mn1—O4—H7B134 (5)
C3—C2—H2110.0H7A—O4—H7B116 (8)
C4—C3—C2105.1 (6)Mn1—O5—H8A132 (5)
C4—C3—H3A110.7Mn1—O5—H8B120 (5)
C2—C3—H3A110.7H8A—O5—H8B92 (7)
C4—C3—H3B110.7
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x+1/2, y+1/2, z+1.
(2a) top
Crystal data top
C10H22Cl2MnN2O6F(000) = 406
Mr = 392.14Dx = 1.659 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2761 reflections
a = 9.124 (3) Åθ = 2.3–26.4°
b = 9.034 (3) ŵ = 1.21 mm1
c = 10.001 (3) ÅT = 100 K
β = 107.704 (4)°Block, colorless
V = 785.2 (4) Å30.30 × 0.20 × 0.20 mm
Z = 2
Data collection top
Bruker D8 goniometer with SMART APEX CCD detector
diffractometer
1630 independent reflections
Radiation source: microsource1445 reflections with I > 2σ(I)
Multi layer optics monochromatorRint = 0.045
ω scansθmax = 26.5°, θmin = 2.3°
Absorption correction: multi-scan
SADABS
h = 1111
Tmin = 0.713, Tmax = 0.794k = 1111
8789 measured reflectionsl = 1212
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)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.037P)2 + 0.3P]
where P = (Fo2 + 2Fc2)/3
1630 reflections(Δ/σ)max = 0.001
139 parametersΔρmax = 0.54 e Å3
3 restraintsΔρmin = 0.22 e Å3
Crystal data top
C10H22Cl2MnN2O6V = 785.2 (4) Å3
Mr = 392.14Z = 2
Monoclinic, P21/cMo Kα radiation
a = 9.124 (3) ŵ = 1.21 mm1
b = 9.034 (3) ÅT = 100 K
c = 10.001 (3) Å0.30 × 0.20 × 0.20 mm
β = 107.704 (4)°
Data collection top
Bruker D8 goniometer with SMART APEX CCD detector
diffractometer
1630 independent reflections
Absorption correction: multi-scan
SADABS
1445 reflections with I > 2σ(I)
Tmin = 0.713, Tmax = 0.794Rint = 0.045
8789 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0283 restraints
wR(F2) = 0.071H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.54 e Å3
1630 reflectionsΔρmin = 0.22 e Å3
139 parameters
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*/UeqOcc. (<1)
Mn10.00000.50000.50000.01557 (13)
Cl10.20028 (5)0.33207 (5)0.44130 (5)0.01996 (14)
O30.07612 (17)0.42942 (16)0.71773 (15)0.0219 (3)
H5A0.100 (3)0.352 (2)0.750 (3)0.034 (7)*
H5B0.103 (3)0.488 (3)0.776 (3)0.044 (9)*
O10.16308 (15)0.68153 (14)0.57041 (13)0.0200 (3)
O20.12745 (18)0.84199 (15)0.39323 (14)0.0288 (3)
C10.1641 (2)0.8090 (2)0.52060 (19)0.0175 (4)
C20.2192 (2)0.9373 (2)0.62190 (19)0.0196 (4)
H20.13681.01460.59910.024*
C3A0.3612 (13)1.0081 (13)0.6280 (14)0.0231 (19)0.510 (8)
H3AA0.36821.10740.67150.028*0.510 (8)
H3BA0.37281.01820.53320.028*0.510 (8)
C4A0.4827 (4)0.9032 (6)0.7194 (5)0.0268 (14)0.510 (8)
H4AA0.57820.95750.76840.032*0.510 (8)
H4BA0.50760.82330.66210.032*0.510 (8)
C5A0.4064 (17)0.8404 (12)0.8244 (14)0.0243 (19)0.510 (8)
H5AA0.41290.73090.82770.029*0.510 (8)
H5BA0.45590.88000.91980.029*0.510 (8)
C3B0.3940 (13)0.9766 (13)0.6176 (15)0.0215 (19)0.490 (8)
H3AB0.43700.89420.57600.026*0.490 (8)
H3BB0.39441.06790.56290.026*0.490 (8)
C4B0.4841 (5)0.9982 (6)0.7710 (5)0.0262 (14)0.490 (8)
H4AB0.59540.98150.78710.031*0.490 (8)
H4BB0.46881.09920.80290.031*0.490 (8)
C5B0.4183 (18)0.8840 (12)0.8449 (15)0.025 (2)0.490 (8)
H5AB0.44150.90840.94570.030*0.490 (8)
H5BB0.46030.78470.83590.030*0.490 (8)
N10.24476 (19)0.88961 (19)0.77046 (16)0.0189 (3)
H1A0.219 (2)0.965 (2)0.818 (2)0.023*
H1B0.185 (2)0.812 (2)0.773 (2)0.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0189 (2)0.0116 (2)0.0147 (2)0.00210 (15)0.00279 (16)0.00012 (15)
Cl10.0235 (3)0.0145 (2)0.0197 (2)0.00172 (17)0.00328 (18)0.00027 (17)
O30.0335 (8)0.0120 (7)0.0165 (7)0.0004 (6)0.0020 (6)0.0001 (6)
O10.0239 (7)0.0131 (7)0.0201 (7)0.0044 (5)0.0025 (5)0.0012 (5)
O20.0500 (10)0.0160 (7)0.0180 (7)0.0009 (7)0.0070 (7)0.0008 (6)
C10.0181 (9)0.0146 (9)0.0194 (9)0.0005 (7)0.0050 (7)0.0010 (7)
C20.0242 (10)0.0135 (9)0.0180 (9)0.0015 (8)0.0017 (8)0.0008 (7)
C3A0.021 (5)0.022 (4)0.025 (3)0.002 (3)0.007 (3)0.004 (3)
C4A0.014 (2)0.031 (3)0.032 (3)0.0008 (17)0.0020 (17)0.002 (2)
C5A0.022 (4)0.026 (5)0.022 (4)0.001 (4)0.002 (3)0.003 (4)
C3B0.015 (5)0.023 (5)0.027 (3)0.009 (3)0.008 (3)0.002 (3)
C4B0.020 (2)0.028 (3)0.026 (2)0.0072 (18)0.0017 (17)0.000 (2)
C5B0.016 (3)0.029 (6)0.022 (4)0.003 (4)0.006 (3)0.002 (4)
N10.0217 (8)0.0173 (8)0.0169 (8)0.0006 (7)0.0048 (7)0.0024 (7)
Geometric parameters (Å, º) top
Mn1—O3i2.1704 (15)C4A—C5A1.535 (15)
Mn1—O32.1704 (15)C4A—H4AA0.9900
Mn1—O12.1820 (13)C4A—H4BA0.9900
Mn1—O1i2.1820 (13)C5A—N11.476 (15)
Mn1—Cl1i2.5763 (7)C5A—H5AA0.9900
Mn1—Cl12.5763 (7)C5A—H5BA0.9900
O3—H5A0.774 (19)C3B—C4B1.516 (15)
O3—H5B0.77 (2)C3B—H3AB0.9900
O1—C11.256 (2)C3B—H3BB0.9900
O2—C11.251 (2)C4B—C5B1.496 (15)
C1—C21.521 (3)C4B—H4AB0.9900
C2—C3A1.429 (13)C4B—H4BB0.9900
C2—N11.496 (2)C5B—N11.532 (15)
C2—C3B1.647 (12)C5B—H5AB0.9900
C2—H21.0000C5B—H5BB0.9900
C3A—C4A1.532 (13)N1—H1A0.903 (16)
C3A—H3AA0.9900N1—H1B0.890 (16)
C3A—H3BA0.9900
O3i—Mn1—O3180.0C3A—C4A—H4AA111.0
O3i—Mn1—O194.69 (5)C5A—C4A—H4AA111.0
O3—Mn1—O185.31 (5)C3A—C4A—H4BA111.0
O3i—Mn1—O1i85.30 (5)C5A—C4A—H4BA111.0
O3—Mn1—O1i94.69 (5)H4AA—C4A—H4BA109.0
O1—Mn1—O1i180.0N1—C5A—C4A104.4 (9)
O3i—Mn1—Cl1i91.31 (4)N1—C5A—H5AA110.9
O3—Mn1—Cl1i88.69 (4)C4A—C5A—H5AA110.9
O1—Mn1—Cl1i86.87 (4)N1—C5A—H5BA110.9
O1i—Mn1—Cl1i93.13 (4)C4A—C5A—H5BA110.9
O3i—Mn1—Cl188.69 (4)H5AA—C5A—H5BA108.9
O3—Mn1—Cl191.31 (4)C4B—C3B—C2103.4 (7)
O1—Mn1—Cl193.13 (4)C4B—C3B—H3AB111.1
O1i—Mn1—Cl186.87 (4)C2—C3B—H3AB111.1
Cl1i—Mn1—Cl1179.9990 (10)C4B—C3B—H3BB111.1
Mn1—O3—H5A130.8 (19)C2—C3B—H3BB111.1
Mn1—O3—H5B120 (2)H3AB—C3B—H3BB109.0
H5A—O3—H5B108 (3)C5B—C4B—C3B103.6 (7)
C1—O1—Mn1130.38 (12)C5B—C4B—H4AB111.0
O2—C1—O1126.18 (17)C3B—C4B—H4AB111.0
O2—C1—C2115.41 (16)C5B—C4B—H4BB111.0
O1—C1—C2118.39 (16)C3B—C4B—H4BB111.0
C3A—C2—N1102.8 (6)H4AB—C4B—H4BB109.0
C3A—C2—C1118.7 (4)C4B—C5B—N1104.4 (9)
N1—C2—C1111.24 (15)C4B—C5B—H5AB110.9
C3A—C2—C3B14.6 (6)N1—C5B—H5AB110.9
N1—C2—C3B103.2 (5)C4B—C5B—H5BB110.9
C1—C2—C3B105.8 (4)N1—C5B—H5BB110.9
C3A—C2—H2107.9H5AB—C5B—H5BB108.9
N1—C2—H2107.9C5A—N1—C2106.7 (6)
C1—C2—H2107.9C5A—N1—C5B16.8 (5)
C3B—C2—H2120.7C2—N1—C5B108.5 (6)
C2—C3A—C4A103.4 (8)C5A—N1—H1A115.4 (15)
C2—C3A—H3AA111.1C2—N1—H1A108.6 (14)
C4A—C3A—H3AA111.1C5B—N1—H1A99.7 (15)
C2—C3A—H3BA111.1C5A—N1—H1B107.6 (15)
C4A—C3A—H3BA111.1C2—N1—H1B109.9 (14)
H3AA—C3A—H3BA109.1C5B—N1—H1B120.6 (15)
C3A—C4A—C5A103.9 (8)H1A—N1—H1B109 (2)
Symmetry code: (i) x, y+1, z+1.
(2b) top
Crystal data top
C10H22Br2MnN2O6F(000) = 478
Mr = 481.06Dx = 1.951 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1326 reflections
a = 9.3156 (12) Åθ = 3.1–22.4°
b = 9.1319 (12) ŵ = 5.71 mm1
c = 10.0593 (13) ÅT = 100 K
β = 106.904 (2)°Block, colorless
V = 818.76 (18) Å30.14 × 0.08 × 0.04 mm
Z = 2
Data collection top
Bruker D8 goniometer with SMART APEX CCD detector
diffractometer
2421 independent reflections
Radiation source: microsource1997 reflections with I > 2σ(I)
Multi layer optics monochromatorRint = 0.066
ω scansθmax = 30.9°, θmin = 3.1°
Absorption correction: multi-scan
SADABS
h = 1313
Tmin = 0.502, Tmax = 0.804k = 1212
12113 measured reflectionsl = 1313
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.020P)2 + 3.P]
where P = (Fo2 + 2Fc2)/3
2421 reflections(Δ/σ)max < 0.001
111 parametersΔρmax = 0.90 e Å3
3 restraintsΔρmin = 0.66 e Å3
Crystal data top
C10H22Br2MnN2O6V = 818.76 (18) Å3
Mr = 481.06Z = 2
Monoclinic, P21/cMo Kα radiation
a = 9.3156 (12) ŵ = 5.71 mm1
b = 9.1319 (12) ÅT = 100 K
c = 10.0593 (13) Å0.14 × 0.08 × 0.04 mm
β = 106.904 (2)°
Data collection top
Bruker D8 goniometer with SMART APEX CCD detector
diffractometer
2421 independent reflections
Absorption correction: multi-scan
SADABS
1997 reflections with I > 2σ(I)
Tmin = 0.502, Tmax = 0.804Rint = 0.066
12113 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0463 restraints
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.90 e Å3
2421 reflectionsΔρmin = 0.66 e Å3
111 parameters
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
Mn10.00000.50000.50000.01456 (17)
Br10.21256 (4)0.31959 (4)0.44867 (4)0.01881 (11)
O30.0633 (4)0.4400 (3)0.7173 (3)0.0217 (6)
H1O0.103 (5)0.371 (5)0.757 (5)0.031 (14)*
H2O0.090 (7)0.502 (6)0.771 (6)0.07 (2)*
O10.1559 (3)0.6797 (3)0.5675 (3)0.0198 (6)
O20.1237 (4)0.8344 (3)0.3892 (3)0.0260 (7)
C10.1613 (4)0.8040 (4)0.5158 (4)0.0155 (7)
C20.2273 (4)0.9295 (4)0.6141 (4)0.0167 (7)
H20.16301.01860.58730.020*
C30.3882 (5)0.9634 (5)0.6109 (4)0.0251 (9)
H3A0.42980.88070.57020.030*
H3B0.39031.05280.55580.030*
C40.4764 (5)0.9861 (6)0.7621 (5)0.0334 (11)
H4A0.58460.96660.77780.040*
H4B0.46351.08690.79330.040*
C50.4064 (5)0.8742 (5)0.8356 (4)0.0277 (9)
H5A0.44220.77400.82480.033*
H5B0.42840.89690.93570.033*
N10.2429 (4)0.8901 (4)0.7621 (3)0.0179 (7)
H1A0.212 (5)0.970 (3)0.802 (4)0.022*
H1B0.188 (4)0.810 (3)0.770 (5)0.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0198 (4)0.0120 (4)0.0110 (4)0.0033 (3)0.0032 (3)0.0000 (3)
Br10.0230 (2)0.01310 (17)0.01790 (18)0.00011 (15)0.00207 (14)0.00006 (15)
O30.0352 (18)0.0120 (13)0.0140 (14)0.0007 (12)0.0010 (12)0.0013 (11)
O10.0215 (14)0.0137 (12)0.0210 (13)0.0028 (11)0.0013 (11)0.0030 (11)
O20.0458 (19)0.0175 (14)0.0130 (13)0.0022 (13)0.0061 (12)0.0017 (11)
C10.0178 (18)0.0142 (17)0.0162 (17)0.0014 (14)0.0075 (14)0.0012 (13)
C20.0192 (19)0.0165 (17)0.0142 (17)0.0008 (14)0.0047 (14)0.0002 (14)
C30.025 (2)0.030 (2)0.022 (2)0.0077 (18)0.0110 (17)0.0015 (17)
C40.024 (2)0.039 (3)0.036 (3)0.008 (2)0.0065 (19)0.004 (2)
C50.025 (2)0.035 (2)0.021 (2)0.0010 (19)0.0021 (17)0.0088 (18)
N10.0236 (18)0.0176 (16)0.0142 (15)0.0018 (13)0.0079 (13)0.0006 (12)
Geometric parameters (Å, º) top
Mn1—O32.162 (3)C2—H21.0000
Mn1—O3i2.162 (3)C3—C41.519 (6)
Mn1—O1i2.166 (3)C3—H3A0.9900
Mn1—O12.166 (3)C3—H3B0.9900
Mn1—Br1i2.7379 (5)C4—C51.516 (6)
Mn1—Br12.7379 (5)C4—H4A0.9900
O3—H1O0.78 (4)C4—H4B0.9900
O3—H2O0.77 (4)C5—N11.494 (5)
O1—C11.255 (4)C5—H5A0.9900
O2—C11.249 (4)C5—H5B0.9900
C1—C21.522 (5)N1—H1A0.922 (19)
C2—N11.498 (5)N1—H1B0.913 (19)
C2—C31.540 (5)
O3—Mn1—O3i180.0C1—C2—H2109.9
O3—Mn1—O1i94.90 (11)C3—C2—H2109.9
O3i—Mn1—O1i85.10 (11)C4—C3—C2104.6 (3)
O3—Mn1—O185.09 (11)C4—C3—H3A110.8
O3i—Mn1—O194.90 (11)C2—C3—H3A110.8
O1i—Mn1—O1180.0C4—C3—H3B110.8
O3—Mn1—Br1i87.79 (8)C2—C3—H3B110.8
O3i—Mn1—Br1i92.21 (8)H3A—C3—H3B108.9
O1i—Mn1—Br1i93.40 (8)C5—C4—C3102.2 (4)
O1—Mn1—Br1i86.60 (8)C5—C4—H4A111.3
O3—Mn1—Br192.21 (8)C3—C4—H4A111.3
O3i—Mn1—Br187.79 (8)C5—C4—H4B111.3
O1i—Mn1—Br186.60 (8)C3—C4—H4B111.3
O1—Mn1—Br193.40 (8)H4A—C4—H4B109.2
Br1i—Mn1—Br1180.0N1—C5—C4102.4 (3)
Mn1—O3—H1O132 (4)N1—C5—H5A111.3
Mn1—O3—H2O117 (5)C4—C5—H5A111.3
H1O—O3—H2O103 (6)N1—C5—H5B111.3
C1—O1—Mn1131.2 (2)C4—C5—H5B111.3
O2—C1—O1126.2 (3)H5A—C5—H5B109.2
O2—C1—C2115.8 (3)C5—N1—C2107.8 (3)
O1—C1—C2117.9 (3)C5—N1—H1A106 (3)
N1—C2—C1111.7 (3)C2—N1—H1A107 (3)
N1—C2—C3104.8 (3)C5—N1—H1B114 (3)
C1—C2—C3110.5 (3)C2—N1—H1B113 (3)
N1—C2—H2109.9H1A—N1—H1B110 (4)
Symmetry code: (i) x, y+1, z+1.
(2c) top
Crystal data top
C10H22I2MnN2O6F(000) = 550
Mr = 575.04Dx = 2.165 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1525 reflections
a = 9.664 (1) Åθ = 3.0–24.4°
b = 9.4026 (10) ŵ = 4.27 mm1
c = 10.0228 (11) ÅT = 100 K
β = 104.454 (2)°Block, yellow
V = 881.91 (16) Å30.09 × 0.09 × 0.09 mm
Z = 2
Data collection top
Bruker D8 goniometer with SMART APEX CCD detector
diffractometer
2622 independent reflections
Radiation source: microsource2151 reflections with I > 2σ(I)
Multi layer optics monochromatorRint = 0.064
ω scansθmax = 30.6°, θmin = 3.0°
Absorption correction: multi-scan
SADABS
h = 1313
Tmin = 0.700, Tmax = 0.700k = 1312
13020 measured reflectionsl = 1414
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.061H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.020P)2]
where P = (Fo2 + 2Fc2)/3
2622 reflections(Δ/σ)max = 0.001
111 parametersΔρmax = 0.88 e Å3
3 restraintsΔρmin = 0.68 e Å3
Crystal data top
C10H22I2MnN2O6V = 881.91 (16) Å3
Mr = 575.04Z = 2
Monoclinic, P21/cMo Kα radiation
a = 9.664 (1) ŵ = 4.27 mm1
b = 9.4026 (10) ÅT = 100 K
c = 10.0228 (11) Å0.09 × 0.09 × 0.09 mm
β = 104.454 (2)°
Data collection top
Bruker D8 goniometer with SMART APEX CCD detector
diffractometer
2622 independent reflections
Absorption correction: multi-scan
SADABS
2151 reflections with I > 2σ(I)
Tmin = 0.700, Tmax = 0.700Rint = 0.064
13020 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0313 restraints
wR(F2) = 0.061H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.88 e Å3
2622 reflectionsΔρmin = 0.68 e Å3
111 parameters
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
Mn10.00000.50000.50000.01263 (15)
I10.23227 (2)0.31229 (2)0.45619 (2)0.01552 (7)
O30.0472 (3)0.4497 (3)0.7170 (2)0.0155 (5)
H1O0.083 (4)0.379 (4)0.751 (4)0.035 (13)*
H2O0.077 (5)0.509 (4)0.771 (4)0.039 (14)*
O10.1415 (2)0.6779 (2)0.5618 (2)0.0164 (5)
O20.1140 (3)0.8249 (2)0.3812 (2)0.0199 (5)
C10.1515 (3)0.7969 (3)0.5069 (3)0.0147 (6)
C20.2231 (3)0.9162 (3)0.5998 (3)0.0143 (6)
H20.16681.00580.57490.017*
C30.3765 (3)0.9394 (4)0.5866 (3)0.0184 (7)
H3A0.41210.85400.54790.022*
H3B0.38121.02180.52640.022*
C40.4636 (4)0.9672 (4)0.7331 (4)0.0235 (8)
H4A0.45571.06770.75970.028*
H4B0.56560.94330.74390.028*
C50.3942 (3)0.8676 (4)0.8174 (4)0.0200 (7)
H5A0.42640.76830.81190.024*
H5B0.41600.89720.91520.024*
N10.2390 (3)0.8832 (3)0.7499 (3)0.0149 (6)
H1A0.206 (3)0.958 (3)0.792 (3)0.018*
H1B0.188 (3)0.802 (3)0.752 (4)0.018*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0170 (4)0.0111 (3)0.0093 (3)0.0029 (3)0.0022 (3)0.0002 (3)
I10.01752 (11)0.01175 (11)0.01572 (11)0.00074 (8)0.00119 (8)0.00082 (8)
O30.0216 (13)0.0121 (12)0.0106 (12)0.0010 (10)0.0002 (10)0.0002 (10)
O10.0206 (12)0.0101 (11)0.0170 (12)0.0027 (9)0.0019 (10)0.0024 (9)
O20.0308 (14)0.0162 (12)0.0117 (11)0.0026 (10)0.0035 (10)0.0017 (9)
C10.0149 (16)0.0147 (16)0.0164 (16)0.0007 (13)0.0075 (13)0.0015 (13)
C20.0153 (16)0.0133 (16)0.0143 (15)0.0014 (12)0.0040 (13)0.0009 (12)
C30.0198 (17)0.0176 (17)0.0197 (17)0.0003 (14)0.0082 (14)0.0006 (14)
C40.0186 (18)0.029 (2)0.0222 (19)0.0049 (15)0.0039 (15)0.0006 (15)
C50.0165 (17)0.0252 (18)0.0172 (16)0.0011 (14)0.0023 (13)0.0016 (15)
N10.0160 (14)0.0153 (14)0.0146 (13)0.0010 (11)0.0059 (11)0.0025 (11)
Geometric parameters (Å, º) top
Mn1—O1i2.151 (2)C2—H21.0000
Mn1—O12.151 (2)C3—C41.521 (5)
Mn1—O3i2.160 (2)C3—H3A0.9900
Mn1—O32.160 (2)C3—H3B0.9900
Mn1—I1i2.9729 (3)C4—C51.524 (5)
Mn1—I12.9730 (3)C4—H4A0.9900
O3—H1O0.79 (3)C4—H4B0.9900
O3—H2O0.78 (3)C5—N11.491 (4)
O1—C11.261 (3)C5—H5A0.9900
O2—C11.249 (4)C5—H5B0.9900
C1—C21.511 (4)N1—H1A0.921 (18)
C2—N11.507 (4)N1—H1B0.910 (18)
C2—C31.536 (4)
O1i—Mn1—O1180.00 (10)C1—C2—H2109.6
O1i—Mn1—O3i85.49 (9)C3—C2—H2109.6
O1—Mn1—O3i94.51 (9)C4—C3—C2104.8 (3)
O1i—Mn1—O394.51 (9)C4—C3—H3A110.8
O1—Mn1—O385.50 (9)C2—C3—H3A110.8
O3i—Mn1—O3180.00 (13)C4—C3—H3B110.8
O1i—Mn1—I1i93.15 (6)C2—C3—H3B110.8
O1—Mn1—I1i86.85 (6)H3A—C3—H3B108.9
O3i—Mn1—I1i92.36 (7)C3—C4—C5102.4 (3)
O3—Mn1—I1i87.64 (7)C3—C4—H4A111.3
O1i—Mn1—I186.85 (6)C5—C4—H4A111.3
O1—Mn1—I193.15 (6)C3—C4—H4B111.3
O3i—Mn1—I187.64 (7)C5—C4—H4B111.3
O3—Mn1—I192.36 (7)H4A—C4—H4B109.2
I1i—Mn1—I1180.0N1—C5—C4102.7 (3)
Mn1—O3—H1O126 (3)N1—C5—H5A111.2
Mn1—O3—H2O120 (3)C4—C5—H5A111.2
H1O—O3—H2O104 (4)N1—C5—H5B111.2
C1—O1—Mn1132.6 (2)C4—C5—H5B111.2
O2—C1—O1126.3 (3)H5A—C5—H5B109.1
O2—C1—C2116.0 (3)C5—N1—C2108.3 (2)
O1—C1—C2117.6 (3)C5—N1—H1A107 (2)
N1—C2—C1112.3 (3)C2—N1—H1A110 (2)
N1—C2—C3104.8 (2)C5—N1—H1B113 (2)
C1—C2—C3110.8 (3)C2—N1—H1B106 (2)
N1—C2—H2109.6H1A—N1—H1B113 (3)
Symmetry code: (i) x, y+1, z+1.

Experimental details

(1a)(1b)(1c)(2a)
Crystal data
Chemical formulaC5H9Cl2MnNO2·H2OC7H17Br2MnNO4C5H15IMnNO5·IC10H22Cl2MnN2O6
Mr258.99393.98477.92392.14
Crystal system, space groupOrthorhombic, P212121Monoclinic, P21Orthorhombic, P212121Monoclinic, P21/c
Temperature (K)100100100100
a, b, c (Å)7.0862 (6), 10.0235 (8), 13.2437 (11)8.286 (2), 8.256 (2), 9.387 (3)8.1264 (18), 11.867 (3), 13.727 (3)9.124 (3), 9.034 (3), 10.001 (3)
α, β, γ (°)90, 90, 9090, 92.172 (4), 9090, 90, 9090, 107.704 (4), 90
V3)940.68 (13)641.7 (3)1323.8 (5)785.2 (4)
Z4242
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)1.947.255.661.21
Crystal size (mm)0.14 × 0.06 × 0.050.27 × 0.08 × 0.080.14 × 0.08 × 0.080.30 × 0.20 × 0.20
Data collection
DiffractometerBruker D8 goniometer with SMART APEX CCD detector
diffractometer
Bruker D8 goniometer with SMART APEX CCD detector
diffractometer
Bruker D8 goniometer with SMART APEX CCD detector
diffractometer
Bruker D8 goniometer with SMART APEX CCD detector
diffractometer
Absorption correctionMulti-scan
SADABS
Multi-scan
SADABS
Multi-scan
SADABS
Multi-scan
SADABS
Tmin, Tmax0.773, 0.9090.245, 0.5950.505, 0.6600.713, 0.794
No. of measured, independent and
observed [I > 2σ(I)] reflections
11373, 2039, 1797 7642, 2665, 2440 15709, 2690, 2412 8789, 1630, 1445
Rint0.0580.0610.0860.045
(sin θ/λ)max1)0.6410.6280.6250.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.074, 1.06 0.035, 0.064, 1.00 0.033, 0.078, 1.03 0.028, 0.071, 1.03
No. of reflections2039266526901630
No. of parameters121152151139
No. of restraints44213
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.52, 0.330.61, 0.481.13, 1.090.54, 0.22
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881?
Absolute structure parameter0.02 (4)0.015 (12)0.05 (5)?


(2b)(2c)
Crystal data
Chemical formulaC10H22Br2MnN2O6C10H22I2MnN2O6
Mr481.06575.04
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)100100
a, b, c (Å)9.3156 (12), 9.1319 (12), 10.0593 (13)9.664 (1), 9.4026 (10), 10.0228 (11)
α, β, γ (°)90, 106.904 (2), 9090, 104.454 (2), 90
V3)818.76 (18)881.91 (16)
Z22
Radiation typeMo KαMo Kα
µ (mm1)5.714.27
Crystal size (mm)0.14 × 0.08 × 0.040.09 × 0.09 × 0.09
Data collection
DiffractometerBruker D8 goniometer with SMART APEX CCD detector
diffractometer
Bruker D8 goniometer with SMART APEX CCD detector
diffractometer
Absorption correctionMulti-scan
SADABS
Multi-scan
SADABS
Tmin, Tmax0.502, 0.8040.700, 0.700
No. of measured, independent and
observed [I > 2σ(I)] reflections
12113, 2421, 1997 13020, 2622, 2151
Rint0.0660.064
(sin θ/λ)max1)0.7230.715
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.088, 1.05 0.031, 0.061, 1.01
No. of reflections24212622
No. of parameters111111
No. of restraints33
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.90, 0.660.88, 0.68
Absolute structure??
Absolute structure parameter??

Computer programs: SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997).

 

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