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Under accelerated and controlled evaporation, chain polymers crystallize from aqueous solutions of CaII and MnII halides with enantiopure L-alanine or racemic DL-alanine. In all ten solids thus obtained zwitterionic amino acid ligands bridge neighbouring cations. The exclusively O-donor-based coordination sphere around the metal cations is completed by aqua ligands; the halides remain uncoordinated and act as counter-anions for the cationic strands. Despite the differences in ionic radii and electronic structure between the main group and the transition metal cation, their derivatives with L-alanine share a common structure type. In contrast, the solids derived from DL-alanine differ and adopt structures depending on the metal cation and the halide. Homochiral chains of either chirality or heterochiral chains with different arrangements of crystallographic inversion centres along the polymer strands are encountered. On average, the six-coordinated CaII cations, devoid of any ligand field effect, show more pronounced deviation from idealized octahedral geometry than the d-block cation MnII.

Supporting information

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Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520614021398/gp5078sup1.cif
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Refinement details, and extra figures and tables

CCDC references: 1018134; 1018135; 1018136; 1018137; 1018138; 1018139; 1018140

Experimental top

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Results and discussion top

Computing details top

For all compounds, program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
[Figure 11]
(1) top
Crystal data top
C9H23CaN3O7·2(Br)Z = 2
Mr = 485.20F(000) = 488
Monoclinic, P21Dx = 1.771 Mg m3
a = 4.8971 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 15.812 (3) ŵ = 4.77 mm1
c = 11.773 (2) ÅT = 100 K
β = 93.746 (3)°Needle, colourless
V = 909.7 (3) Å30.30 × 0.06 × 0.03 mm
Data collection top
Bruker APEX CCD
diffractometer
3731 independent reflections
Radiation source: microsource3445 reflections with I > 2σ(I)
Multilayer optics monochromatorRint = 0.074
ω scansθmax = 26.4°, θmin = 1.7°
Absorption correction: multi-scan
SADABS
h = 66
Tmin = 0.455, Tmax = 0.745k = 1919
10950 measured reflectionsl = 1414
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.042 w = 1/[σ2(Fo2) + (0.039P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.099(Δ/σ)max = 0.003
S = 1.02Δρmax = 0.67 e Å3
3731 reflectionsΔρmin = 0.67 e Å3
235 parametersAbsolute structure: Flack x determined using 1513 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61).
38 restraintsAbsolute structure parameter: 0.007 (13)
Crystal data top
C9H23CaN3O7·2(Br)V = 909.7 (3) Å3
Mr = 485.20Z = 2
Monoclinic, P21Mo Kα radiation
a = 4.8971 (9) ŵ = 4.77 mm1
b = 15.812 (3) ÅT = 100 K
c = 11.773 (2) Å0.30 × 0.06 × 0.03 mm
β = 93.746 (3)°
Data collection top
Bruker APEX CCD
diffractometer
3731 independent reflections
Absorption correction: multi-scan
SADABS
3445 reflections with I > 2σ(I)
Tmin = 0.455, Tmax = 0.745Rint = 0.074
10950 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.099Δρmax = 0.67 e Å3
S = 1.02Δρmin = 0.67 e Å3
3731 reflectionsAbsolute structure: Flack x determined using 1513 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61).
235 parametersAbsolute structure parameter: 0.007 (13)
38 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ca10.9046 (3)0.75000 (11)0.06889 (14)0.0095 (3)
Br10.62601 (18)0.64760 (5)0.46238 (6)0.0198 (2)
Br20.80165 (16)0.36363 (4)0.32036 (6)0.0151 (2)
O10.2738 (11)0.6854 (3)0.1640 (5)0.0134 (12)
O20.6857 (11)0.6305 (3)0.1400 (5)0.0142 (13)
C10.4435 (16)0.6270 (5)0.1705 (6)0.0115 (17)
C20.3493 (15)0.5403 (5)0.2125 (7)0.0106 (16)
H2A0.50100.51370.26110.013*
C30.274 (2)0.4832 (6)0.1114 (8)0.023 (2)
H3A0.20910.42870.13860.034*
H3B0.43610.47410.06800.034*
H3C0.12990.51000.06230.034*
N10.1083 (15)0.5528 (5)0.2812 (6)0.0133 (14)
H1N0.136 (19)0.585 (5)0.344 (5)0.016*
H2N0.028 (13)0.577 (5)0.239 (6)0.016*
H3N0.066 (19)0.502 (3)0.306 (7)0.016*
O30.5333 (10)0.7620 (4)0.0654 (4)0.0115 (12)
O40.1190 (11)0.7043 (3)0.0977 (5)0.0126 (12)
C40.3632 (17)0.7164 (5)0.1203 (6)0.0129 (17)
C50.4584 (17)0.6686 (5)0.2224 (6)0.0129 (17)
H5A0.30220.66320.28100.015*
C60.5589 (19)0.5813 (5)0.1876 (7)0.0180 (18)
H6A0.62860.55250.25350.027*
H6B0.40730.54860.15950.027*
H6C0.70570.58620.12730.027*
N20.6828 (15)0.7171 (5)0.2713 (6)0.0130 (14)
H4N0.844 (11)0.714 (6)0.232 (7)0.016*
H5N0.714 (18)0.693 (5)0.338 (5)0.016*
H6N0.643 (18)0.771 (3)0.289 (7)0.016*
O50.7518 (12)0.8303 (4)0.2094 (5)0.0161 (12)
O60.3726 (11)0.8859 (3)0.2718 (4)0.0135 (12)
C70.6146 (15)0.8613 (5)0.2845 (6)0.0128 (15)
C80.7586 (15)0.8745 (5)0.4012 (6)0.0120 (16)
H8A0.62980.86030.46090.014*
C90.8480 (19)0.9678 (6)0.4150 (7)0.0189 (19)
H9A0.97780.97340.48150.028*
H9B0.68721.00320.42540.028*
H9C0.93560.98620.34660.028*
N31.0034 (14)0.8185 (4)0.4153 (6)0.0137 (14)
H7N1.079 (18)0.826 (6)0.486 (4)0.016*
H8N0.957 (18)0.764 (3)0.406 (7)0.016*
H9N1.118 (15)0.834 (5)0.362 (6)0.016*
O1W1.1758 (12)0.8728 (4)0.0495 (5)0.0159 (13)
H1W1.241 (19)0.880 (6)0.109 (6)0.019*
H2W1.292 (17)0.856 (7)0.018 (7)0.019*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ca10.0084 (7)0.0084 (7)0.0115 (6)0.0002 (6)0.0014 (5)0.0000 (6)
Br10.0271 (5)0.0175 (4)0.0147 (4)0.0089 (4)0.0005 (3)0.0022 (3)
Br20.0176 (4)0.0105 (4)0.0165 (4)0.0022 (3)0.0040 (3)0.0009 (3)
O10.010 (3)0.007 (3)0.023 (3)0.001 (2)0.005 (2)0.004 (2)
O20.008 (3)0.015 (3)0.019 (3)0.002 (2)0.001 (2)0.003 (2)
C10.012 (4)0.012 (4)0.009 (4)0.002 (3)0.003 (3)0.002 (3)
C20.007 (4)0.008 (4)0.017 (4)0.000 (3)0.002 (3)0.001 (3)
C30.027 (5)0.017 (5)0.026 (5)0.007 (4)0.005 (4)0.005 (4)
N10.012 (4)0.010 (3)0.018 (4)0.001 (3)0.000 (3)0.003 (3)
O30.011 (3)0.011 (3)0.012 (2)0.002 (2)0.004 (2)0.002 (2)
O40.007 (3)0.015 (3)0.015 (3)0.002 (2)0.001 (2)0.003 (2)
C40.016 (4)0.013 (4)0.008 (3)0.005 (3)0.003 (3)0.003 (3)
C50.015 (4)0.008 (4)0.015 (4)0.002 (3)0.001 (3)0.000 (3)
C60.023 (5)0.010 (4)0.021 (4)0.002 (4)0.001 (4)0.001 (3)
N20.012 (4)0.016 (4)0.011 (3)0.001 (3)0.001 (3)0.003 (3)
O50.015 (3)0.019 (3)0.015 (3)0.001 (2)0.002 (2)0.008 (2)
O60.011 (3)0.013 (3)0.016 (3)0.000 (2)0.001 (2)0.001 (2)
C70.013 (4)0.006 (3)0.020 (4)0.003 (4)0.004 (3)0.000 (3)
C80.006 (3)0.014 (4)0.016 (4)0.003 (3)0.001 (3)0.003 (3)
C90.023 (5)0.016 (4)0.018 (4)0.000 (4)0.006 (4)0.008 (4)
N30.008 (4)0.012 (4)0.021 (4)0.001 (3)0.002 (3)0.001 (3)
O1W0.017 (3)0.014 (3)0.016 (3)0.002 (3)0.002 (2)0.003 (3)
Geometric parameters (Å, º) top
Ca1—O52.251 (6)C4—C51.519 (11)
Ca1—O1i2.302 (5)C5—N21.487 (10)
Ca1—O32.338 (5)C5—C61.514 (11)
Ca1—O22.353 (6)C5—H5A1.0000
Ca1—O1W2.372 (6)C6—H6A0.9800
Ca1—O4i2.396 (6)C6—H6B0.9800
Ca1—H1W2.66 (10)C6—H6C0.9800
Ca1—H2W2.63 (10)N2—H4N0.89 (3)
O1—C11.242 (9)N2—H5N0.90 (3)
O1—Ca1ii2.302 (5)N2—H6N0.89 (3)
O2—C11.262 (9)O5—C71.246 (9)
C1—C21.538 (11)O6—C71.247 (9)
C2—N11.487 (10)C7—C81.518 (10)
C2—C31.520 (12)C8—N31.491 (10)
C2—H2A1.0000C8—C91.545 (12)
C3—H3A0.9800C8—H8A1.0000
C3—H3B0.9800C9—H9A0.9800
C3—H3C0.9800C9—H9B0.9800
N1—H1N0.90 (3)C9—H9C0.9800
N1—H2N0.89 (3)N3—H7N0.90 (3)
N1—H3N0.89 (3)N3—H8N0.90 (3)
O3—C41.249 (9)N3—H9N0.90 (3)
O4—C41.257 (10)O1W—H1W0.76 (6)
O4—Ca1ii2.396 (6)O1W—H2W0.75 (6)
O5—Ca1—O1i100.4 (2)H2N—N1—H3N113 (8)
O5—Ca1—O399.8 (2)C4—O3—Ca1140.0 (5)
O1i—Ca1—O3156.4 (2)C4—O4—Ca1ii127.0 (5)
O5—Ca1—O290.6 (2)O3—C4—O4126.1 (7)
O1i—Ca1—O280.36 (19)O3—C4—C5117.9 (7)
O3—Ca1—O287.3 (2)O4—C4—C5115.9 (7)
O5—Ca1—O1W79.9 (2)N2—C5—C6109.9 (7)
O1i—Ca1—O1W89.0 (2)N2—C5—C4108.8 (6)
O3—Ca1—O1W106.5 (2)C6—C5—C4110.6 (6)
O2—Ca1—O1W164.3 (2)N2—C5—H5A109.2
O5—Ca1—O4i162.9 (2)C6—C5—H5A109.2
O1i—Ca1—O4i83.8 (2)C4—C5—H5A109.2
O3—Ca1—O4i80.45 (19)C5—C6—H6A109.5
O2—Ca1—O4i106.5 (2)C5—C6—H6B109.5
O1W—Ca1—O4i83.7 (2)H6A—C6—H6B109.5
O5—Ca1—H1W70.5 (19)C5—C6—H6C109.5
O1i—Ca1—H1W78 (2)H6A—C6—H6C109.5
O3—Ca1—H1W120.1 (18)H6B—C6—H6C109.5
O2—Ca1—H1W148.3 (16)C5—N2—H4N115 (6)
O1W—Ca1—H1W16.0 (15)C5—N2—H5N108 (6)
O4i—Ca1—H1W94.5 (18)H4N—N2—H5N104 (8)
O5—Ca1—H2W95.1 (17)C5—N2—H6N115 (6)
O1i—Ca1—H2W81 (2)H4N—N2—H6N111 (8)
O3—Ca1—H2W110 (2)H5N—N2—H6N104 (8)
O2—Ca1—H2W161 (2)C7—O5—Ca1164.6 (6)
O1W—Ca1—H2W16.3 (17)O5—C7—O6126.2 (7)
O4i—Ca1—H2W69.0 (17)O5—C7—C8117.2 (7)
H1W—Ca1—H2W26 (3)O6—C7—C8116.6 (7)
C1—O1—Ca1ii149.5 (5)N3—C8—C7110.0 (6)
C1—O2—Ca1126.5 (5)N3—C8—C9109.6 (6)
O1—C1—O2125.9 (7)C7—C8—C9109.8 (7)
O1—C1—C2118.0 (7)N3—C8—H8A109.2
O2—C1—C2116.0 (7)C7—C8—H8A109.2
N1—C2—C3110.2 (7)C9—C8—H8A109.2
N1—C2—C1108.8 (6)C8—C9—H9A109.5
C3—C2—C1109.9 (6)C8—C9—H9B109.5
N1—C2—H2A109.3H9A—C9—H9B109.5
C3—C2—H2A109.3C8—C9—H9C109.5
C1—C2—H2A109.3H9A—C9—H9C109.5
C2—C3—H3A109.5H9B—C9—H9C109.5
C2—C3—H3B109.5C8—N3—H7N108 (6)
H3A—C3—H3B109.5C8—N3—H8N111 (6)
C2—C3—H3C109.5H7N—N3—H8N109 (8)
H3A—C3—H3C109.5C8—N3—H9N107 (6)
H3B—C3—H3C109.5H7N—N3—H9N112 (8)
C2—N1—H1N116 (6)H8N—N3—H9N110 (8)
C2—N1—H2N110 (6)Ca1—O1W—H1W104 (8)
H1N—N1—H2N106 (8)Ca1—O1W—H2W102 (8)
C2—N1—H3N106 (6)H1W—O1W—H2W103 (10)
H1N—N1—H3N106 (8)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
(2) top
Crystal data top
C9H23CaN3O7·2(I)Z = 2
Mr = 579.18F(000) = 560
Monoclinic, P21Dx = 1.981 Mg m3
a = 4.9164 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 16.416 (3) ŵ = 3.53 mm1
c = 12.039 (2) ÅT = 100 K
β = 92.435 (3)°Needle, colourless
V = 970.8 (3) Å30.20 × 0.04 × 0.03 mm
Data collection top
Bruker APEX CCD
diffractometer
3955 independent reflections
Radiation source: microsource3580 reflections with I > 2σ(I)
Multilayer optics monochromatorRint = 0.063
ω scansθmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan
SADABS
h = 66
Tmin = 0.554, Tmax = 0.745k = 2020
11583 measured reflectionsl = 1515
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.036 w = 1/[σ2(Fo2) + (0.014P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.065(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.71 e Å3
3955 reflectionsΔρmin = 0.61 e Å3
235 parametersAbsolute structure: Flack x determined using 1553 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61).
50 restraintsAbsolute structure parameter: 0.04 (3)
Crystal data top
C9H23CaN3O7·2(I)V = 970.8 (3) Å3
Mr = 579.18Z = 2
Monoclinic, P21Mo Kα radiation
a = 4.9164 (8) ŵ = 3.53 mm1
b = 16.416 (3) ÅT = 100 K
c = 12.039 (2) Å0.20 × 0.04 × 0.03 mm
β = 92.435 (3)°
Data collection top
Bruker APEX CCD
diffractometer
3955 independent reflections
Absorption correction: multi-scan
SADABS
3580 reflections with I > 2σ(I)
Tmin = 0.554, Tmax = 0.745Rint = 0.063
11583 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.065Δρmax = 0.71 e Å3
S = 1.03Δρmin = 0.61 e Å3
3955 reflectionsAbsolute structure: Flack x determined using 1553 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61).
235 parametersAbsolute structure parameter: 0.04 (3)
50 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.77508 (13)0.36750 (3)0.32244 (5)0.01822 (16)
I20.62059 (14)0.64888 (4)0.45882 (5)0.02179 (17)
Ca10.9183 (4)0.75002 (12)0.06479 (17)0.0120 (4)
O1W1.1891 (13)0.8687 (5)0.0436 (5)0.0167 (14)
H1W1.303 (17)0.849 (6)0.001 (7)0.020*
H2W1.271 (18)0.880 (6)0.104 (6)0.020*
O10.2805 (13)0.6869 (4)0.1558 (5)0.0165 (15)
O20.6910 (13)0.6334 (4)0.1296 (5)0.0182 (16)
C10.4470 (19)0.6301 (5)0.1596 (7)0.013 (2)
C20.348 (2)0.5470 (6)0.1982 (8)0.016 (2)
H20.49670.52070.24490.019*
C30.279 (3)0.4925 (6)0.0994 (9)0.028 (3)
H3A0.21590.43950.12580.041*
H3B0.44130.48480.05610.041*
H3C0.13490.51790.05250.041*
N10.1079 (17)0.5577 (5)0.2663 (7)0.0126 (18)
H1N0.034 (13)0.581 (5)0.221 (6)0.015*
H2N0.174 (17)0.584 (5)0.332 (5)0.015*
H3N0.058 (18)0.505 (3)0.291 (7)0.015*
O30.5575 (15)0.7602 (5)0.0660 (6)0.0160 (14)
O40.1440 (14)0.7032 (4)0.0950 (6)0.0174 (16)
C40.389 (2)0.7165 (6)0.1182 (8)0.016 (2)
C50.4883 (19)0.6697 (5)0.2183 (8)0.014 (2)
H50.33780.66650.27660.017*
C60.578 (2)0.5832 (6)0.1856 (9)0.021 (2)
H6A0.64330.55490.25100.032*
H6B0.42380.55340.15660.032*
H6C0.72560.58600.12820.032*
N20.7248 (18)0.7148 (5)0.2641 (7)0.0144 (18)
H4N0.648 (18)0.766 (3)0.283 (8)0.017*
H5N0.744 (19)0.703 (6)0.341 (3)0.017*
H6N0.882 (13)0.717 (6)0.215 (7)0.017*
O50.7670 (14)0.8290 (4)0.2022 (6)0.0193 (16)
O60.3879 (13)0.8871 (4)0.2589 (5)0.0196 (16)
N31.0119 (18)0.8253 (5)0.4015 (7)0.018 (2)
H7N0.950 (19)0.770 (3)0.399 (8)0.022*
H8N1.129 (17)0.841 (5)0.344 (6)0.022*
H9N1.092 (18)0.838 (6)0.473 (4)0.022*
C70.6250 (19)0.8623 (6)0.2739 (7)0.016 (2)
C80.7610 (18)0.8762 (6)0.3884 (7)0.0135 (19)
H80.63180.86050.44670.016*
C90.837 (2)0.9659 (6)0.4028 (9)0.027 (3)
H9A0.94690.97290.47210.041*
H9B0.67140.99870.40570.041*
H9C0.94290.98350.33990.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0214 (4)0.0132 (3)0.0198 (3)0.0021 (3)0.0029 (3)0.0015 (3)
I20.0281 (4)0.0218 (3)0.0155 (3)0.0075 (3)0.0017 (3)0.0027 (3)
Ca10.0118 (9)0.0129 (9)0.0113 (9)0.0008 (8)0.0005 (7)0.0001 (7)
O1W0.018 (4)0.019 (3)0.013 (3)0.002 (4)0.002 (3)0.004 (4)
O10.016 (4)0.013 (3)0.021 (4)0.006 (3)0.001 (3)0.002 (3)
O20.013 (4)0.019 (4)0.022 (4)0.001 (3)0.003 (3)0.001 (3)
C10.016 (5)0.014 (5)0.010 (5)0.001 (4)0.002 (4)0.001 (4)
C20.015 (5)0.014 (5)0.018 (5)0.000 (4)0.002 (4)0.002 (4)
C30.035 (7)0.023 (7)0.025 (6)0.007 (5)0.002 (5)0.001 (5)
N10.006 (4)0.016 (4)0.016 (5)0.001 (3)0.003 (3)0.002 (3)
O30.019 (4)0.018 (3)0.011 (3)0.004 (3)0.003 (3)0.001 (3)
O40.014 (4)0.021 (4)0.017 (4)0.001 (3)0.002 (3)0.005 (3)
C40.017 (6)0.016 (5)0.014 (5)0.004 (4)0.001 (4)0.010 (4)
C50.013 (5)0.016 (5)0.015 (5)0.002 (4)0.007 (4)0.001 (4)
C60.026 (6)0.011 (5)0.026 (6)0.001 (5)0.002 (5)0.000 (4)
N20.017 (5)0.018 (4)0.009 (4)0.007 (4)0.002 (4)0.001 (4)
O50.014 (4)0.023 (4)0.021 (4)0.000 (3)0.001 (3)0.007 (3)
O60.015 (4)0.020 (4)0.024 (4)0.003 (3)0.001 (3)0.001 (3)
N30.018 (5)0.015 (5)0.022 (5)0.004 (4)0.001 (4)0.000 (4)
C70.024 (6)0.011 (4)0.013 (5)0.006 (5)0.000 (4)0.002 (4)
C80.013 (3)0.017 (4)0.011 (3)0.003 (3)0.005 (3)0.002 (3)
C90.034 (6)0.019 (5)0.027 (5)0.001 (4)0.008 (5)0.016 (4)
Geometric parameters (Å, º) top
Ca1—O52.253 (7)O3—C41.245 (12)
Ca1—O1i2.298 (7)O4—C41.267 (11)
Ca1—O32.327 (7)O4—Ca1ii2.388 (7)
Ca1—O22.365 (7)C4—C51.527 (12)
Ca1—O1W2.380 (8)C5—N21.503 (12)
Ca1—O4i2.388 (7)C5—C61.534 (13)
O1—C11.241 (10)O5—C71.258 (11)
O1—Ca1ii2.298 (7)O6—C71.241 (11)
O2—C11.269 (10)N3—C81.492 (12)
C1—C21.528 (12)C7—C81.523 (12)
C2—N11.477 (12)C8—C91.527 (14)
C2—C31.515 (14)
O5—Ca1—O1i100.5 (3)O2—C1—C2116.2 (8)
O5—Ca1—O3100.9 (3)N1—C2—C3110.4 (8)
O1i—Ca1—O3155.2 (3)N1—C2—C1109.6 (8)
O5—Ca1—O292.8 (2)C3—C2—C1110.6 (8)
O1i—Ca1—O281.1 (2)C4—O3—Ca1140.5 (7)
O3—Ca1—O285.6 (2)C4—O4—Ca1ii126.9 (6)
O5—Ca1—O1W79.1 (2)O3—C4—O4127.3 (9)
O1i—Ca1—O1W89.7 (2)O3—C4—C5117.3 (9)
O3—Ca1—O1W106.4 (3)O4—C4—C5115.2 (9)
O2—Ca1—O1W166.5 (2)N2—C5—C4108.7 (7)
O5—Ca1—O4i162.9 (3)N2—C5—C6109.4 (8)
O1i—Ca1—O4i82.0 (2)C4—C5—C6111.2 (8)
O3—Ca1—O4i81.1 (3)C7—O5—Ca1164.6 (6)
O2—Ca1—O4i104.3 (2)O6—C7—O5126.0 (9)
O1W—Ca1—O4i84.0 (2)O6—C7—C8117.1 (8)
C1—O1—Ca1ii148.5 (6)O5—C7—C8116.8 (8)
C1—O2—Ca1126.5 (6)N3—C8—C7109.9 (8)
O1—C1—O2126.0 (9)N3—C8—C9109.2 (8)
O1—C1—C2117.7 (8)C7—C8—C9110.1 (8)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
(3) top
Crystal data top
C9H23MnN3O7·2(Br)Z = 2
Mr = 500.06F(000) = 498
Monoclinic, P21Dx = 1.905 Mg m3
a = 4.7809 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 15.7146 (13) ŵ = 5.38 mm1
c = 11.6246 (10) ÅT = 100 K
β = 93.581 (1)°Block, colourless
V = 871.65 (13) Å30.19 × 0.15 × 0.07 mm
Data collection top
Bruker APEX CCD
diffractometer
4600 independent reflections
Radiation source: microsource4269 reflections with I > 2σ(I)
Multilayer optics monochromatorRint = 0.046
ω scansθmax = 29.0°, θmin = 2.2°
Absorption correction: multi-scan
SADABS
h = 66
Tmin = 0.486, Tmax = 0.746k = 2121
12613 measured reflectionsl = 1515
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.030 w = 1/[σ2(Fo2) + (0.020P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.059(Δ/σ)max = 0.001
S = 1.00Δρmax = 0.46 e Å3
4600 reflectionsΔρmin = 0.35 e Å3
234 parametersAbsolute structure: Flack x determined using 1890 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61).
12 restraintsAbsolute structure parameter: 0.028 (7)
Crystal data top
C9H23MnN3O7·2(Br)V = 871.65 (13) Å3
Mr = 500.06Z = 2
Monoclinic, P21Mo Kα radiation
a = 4.7809 (4) ŵ = 5.38 mm1
b = 15.7146 (13) ÅT = 100 K
c = 11.6246 (10) Å0.19 × 0.15 × 0.07 mm
β = 93.581 (1)°
Data collection top
Bruker APEX CCD
diffractometer
4600 independent reflections
Absorption correction: multi-scan
SADABS
4269 reflections with I > 2σ(I)
Tmin = 0.486, Tmax = 0.746Rint = 0.046
12613 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.059Δρmax = 0.46 e Å3
S = 1.00Δρmin = 0.35 e Å3
4600 reflectionsAbsolute structure: Flack x determined using 1890 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61).
234 parametersAbsolute structure parameter: 0.028 (7)
12 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Mn10.90766 (15)0.74999 (5)0.06999 (6)0.00787 (14)
Br10.79653 (10)0.36550 (3)0.31414 (4)0.01299 (11)
Br20.61843 (10)0.64821 (3)0.46537 (4)0.01540 (12)
O10.2712 (7)0.6937 (2)0.1663 (3)0.0106 (7)
O20.6911 (6)0.6388 (2)0.1310 (3)0.0121 (7)
C10.4438 (9)0.6349 (3)0.1655 (4)0.0092 (9)
C20.3558 (10)0.5469 (3)0.2053 (4)0.0106 (9)
H20.51470.52060.25280.013*
C30.2774 (11)0.4897 (3)0.1029 (4)0.0175 (11)
H3A0.22140.43370.13050.026*
H3B0.43900.48340.05570.026*
H3C0.12110.51520.05630.026*
N10.1096 (9)0.5568 (3)0.2780 (4)0.0109 (8)
H1N0.054 (11)0.504 (2)0.296 (4)0.013*
H2N0.029 (8)0.588 (3)0.242 (4)0.013*
H3N0.160 (11)0.585 (3)0.345 (3)0.013*
O30.5479 (7)0.7651 (2)0.0571 (3)0.0093 (7)
O40.1248 (7)0.7031 (2)0.0831 (3)0.0110 (7)
C40.3735 (9)0.7172 (3)0.1103 (4)0.0085 (9)
C50.4672 (10)0.6687 (3)0.2145 (4)0.0102 (9)
H50.30500.66430.27290.012*
C60.5648 (11)0.5800 (3)0.1821 (5)0.0171 (11)
H6A0.62280.55030.25080.026*
H6B0.41130.54860.14950.026*
H6C0.72390.58340.12480.026*
N20.6946 (9)0.7180 (3)0.2655 (4)0.0115 (8)
H4N0.649 (11)0.7744 (19)0.277 (5)0.014*
H5N0.723 (11)0.691 (3)0.334 (3)0.014*
H6N0.855 (8)0.717 (3)0.223 (4)0.014*
O50.7764 (7)0.8219 (2)0.2086 (3)0.0146 (7)
O60.3859 (7)0.8844 (2)0.2654 (3)0.0129 (7)
C70.6313 (9)0.8570 (3)0.2812 (4)0.0117 (9)
C80.7722 (9)0.8727 (3)0.4010 (4)0.0105 (9)
H80.63750.85900.46080.013*
C90.8616 (11)0.9657 (3)0.4131 (5)0.0183 (11)
H9A0.98190.97290.48380.027*
H9B0.69501.00170.41670.027*
H9C0.96520.98220.34650.027*
N31.0218 (9)0.8160 (3)0.4166 (4)0.0123 (8)
H7N0.949 (11)0.763 (2)0.417 (5)0.015*
H8N1.101 (10)0.826 (4)0.490 (3)0.015*
H9N1.136 (10)0.828 (3)0.361 (4)0.015*
O1W1.1545 (7)0.8656 (2)0.0490 (3)0.0117 (6)
H1W1.286 (8)0.856 (4)0.010 (4)0.014*
H2W1.228 (10)0.872 (4)0.113 (3)0.014*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0065 (3)0.0092 (3)0.0079 (3)0.0002 (3)0.0002 (2)0.0001 (3)
Br10.0143 (2)0.0112 (2)0.0131 (2)0.0020 (2)0.00191 (17)0.00100 (19)
Br20.0193 (3)0.0161 (3)0.0107 (2)0.0058 (2)0.00069 (18)0.0016 (2)
O10.0096 (16)0.0095 (17)0.0126 (17)0.0012 (13)0.0001 (13)0.0012 (14)
O20.0076 (15)0.0122 (18)0.0165 (17)0.0020 (14)0.0018 (13)0.0030 (15)
C10.006 (2)0.015 (3)0.007 (2)0.0010 (18)0.0027 (16)0.0025 (18)
C20.006 (2)0.013 (2)0.013 (2)0.0000 (18)0.0029 (17)0.0028 (19)
C30.022 (3)0.013 (3)0.017 (3)0.003 (2)0.003 (2)0.004 (2)
N10.009 (2)0.011 (2)0.013 (2)0.0027 (16)0.0011 (16)0.0008 (17)
O30.0090 (16)0.0113 (17)0.0075 (16)0.0001 (13)0.0010 (12)0.0008 (13)
O40.0082 (16)0.0160 (18)0.0088 (16)0.0020 (13)0.0000 (13)0.0030 (13)
C40.009 (2)0.009 (2)0.008 (2)0.0033 (17)0.0011 (17)0.0028 (17)
C50.009 (2)0.012 (2)0.009 (2)0.0021 (18)0.0002 (17)0.0042 (18)
C60.020 (3)0.013 (3)0.018 (3)0.002 (2)0.004 (2)0.002 (2)
N20.010 (2)0.016 (2)0.0084 (19)0.0006 (17)0.0011 (16)0.0006 (17)
O50.0093 (16)0.022 (2)0.0131 (17)0.0026 (15)0.0044 (14)0.0088 (15)
O60.0111 (16)0.0129 (18)0.0145 (17)0.0002 (13)0.0011 (13)0.0004 (13)
C70.011 (2)0.008 (2)0.015 (2)0.0044 (19)0.0015 (18)0.001 (2)
C80.009 (2)0.014 (2)0.008 (2)0.001 (2)0.0025 (16)0.000 (2)
C90.020 (3)0.013 (2)0.021 (3)0.000 (2)0.006 (2)0.003 (2)
N30.012 (2)0.014 (2)0.011 (2)0.0000 (17)0.0007 (16)0.0007 (17)
O1W0.0111 (16)0.0136 (16)0.0104 (16)0.0001 (16)0.0005 (12)0.0008 (16)
Geometric parameters (Å, º) top
Mn1—O52.097 (3)C5—N21.488 (6)
Mn1—O22.173 (3)C5—C61.511 (7)
Mn1—O1W2.189 (4)C5—H51.0000
Mn1—O1i2.194 (3)C6—H6A0.9800
Mn1—O32.209 (3)C6—H6B0.9800
Mn1—O4i2.241 (3)C6—H6C0.9800
O1—C11.239 (6)N2—H4N0.92 (3)
O1—Mn1ii2.194 (3)N2—H5N0.92 (3)
O2—C11.274 (5)N2—H6N0.89 (3)
C1—C21.526 (6)O5—C71.253 (5)
C2—N11.499 (6)O6—C71.253 (5)
C2—C31.521 (7)C7—C81.529 (6)
C2—H21.0000C8—N31.492 (6)
C3—H3A0.9800C8—C91.526 (7)
C3—H3B0.9800C8—H81.0000
C3—H3C0.9800C9—H9A0.9800
N1—H1N0.91 (3)C9—H9B0.9800
N1—H2N0.91 (3)C9—H9C0.9800
N1—H3N0.91 (3)N3—H7N0.91 (3)
O3—C41.257 (5)N3—H8N0.92 (3)
O4—C41.269 (6)N3—H9N0.89 (3)
O4—Mn1ii2.241 (3)O1W—H1W0.81 (3)
C4—C51.522 (6)O1W—H2W0.81 (3)
O5—Mn1—O290.64 (14)N2—C5—C6111.0 (4)
O5—Mn1—O1W80.07 (13)N2—C5—C4108.4 (4)
O2—Mn1—O1W167.29 (13)C6—C5—C4111.4 (4)
O5—Mn1—O1i95.19 (13)N2—C5—H5108.7
O2—Mn1—O1i83.55 (12)C6—C5—H5108.7
O1W—Mn1—O1i88.64 (12)C4—C5—H5108.7
O5—Mn1—O3101.43 (13)C5—C6—H6A109.5
O2—Mn1—O386.44 (12)C5—C6—H6B109.5
O1W—Mn1—O3103.80 (13)H6A—C6—H6B109.5
O1i—Mn1—O3160.67 (12)C5—C6—H6C109.5
O5—Mn1—O4i164.57 (13)H6A—C6—H6C109.5
O2—Mn1—O4i104.37 (13)H6B—C6—H6C109.5
O1W—Mn1—O4i84.54 (12)C5—N2—H4N113 (3)
O1i—Mn1—O4i83.18 (12)C5—N2—H5N105 (3)
O3—Mn1—O4i83.35 (11)H4N—N2—H5N111 (5)
C1—O1—Mn1ii143.4 (3)C5—N2—H6N113 (4)
C1—O2—Mn1127.7 (3)H4N—N2—H6N107 (5)
O1—C1—O2126.8 (4)H5N—N2—H6N108 (5)
O1—C1—C2118.5 (4)C7—O5—Mn1163.7 (3)
O2—C1—C2114.7 (4)O6—C7—O5127.3 (4)
N1—C2—C3109.8 (4)O6—C7—C8115.7 (4)
N1—C2—C1108.6 (4)O5—C7—C8117.0 (4)
C3—C2—C1110.9 (4)N3—C8—C9110.1 (4)
N1—C2—H2109.2N3—C8—C7108.5 (4)
C3—C2—H2109.2C9—C8—C7110.1 (4)
C1—C2—H2109.2N3—C8—H8109.4
C2—C3—H3A109.5C9—C8—H8109.4
C2—C3—H3B109.5C7—C8—H8109.4
H3A—C3—H3B109.5C8—C9—H9A109.5
C2—C3—H3C109.5C8—C9—H9B109.5
H3A—C3—H3C109.5H9A—C9—H9B109.5
H3B—C3—H3C109.5C8—C9—H9C109.5
C2—N1—H1N107 (3)H9A—C9—H9C109.5
C2—N1—H2N112 (3)H9B—C9—H9C109.5
H1N—N1—H2N113 (5)C8—N3—H7N105 (3)
C2—N1—H3N111 (3)C8—N3—H8N107 (3)
H1N—N1—H3N108 (5)H7N—N3—H8N107 (5)
H2N—N1—H3N106 (5)C8—N3—H9N108 (4)
C4—O3—Mn1136.8 (3)H7N—N3—H9N117 (5)
C4—O4—Mn1ii128.9 (3)H8N—N3—H9N114 (5)
O3—C4—O4125.8 (4)Mn1—O1W—H1W111 (4)
O3—C4—C5118.2 (4)Mn1—O1W—H2W101 (4)
O4—C4—C5115.9 (4)H1W—O1W—H2W103 (5)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
(4) top
Crystal data top
C9H23MnN3O7·2(I)Z = 2
Mr = 594.04F(000) = 570
Monoclinic, P21Dx = 2.130 Mg m3
a = 4.7932 (16) ÅMo Kα radiation, λ = 0.71073 Å
b = 16.261 (5) ŵ = 4.08 mm1
c = 11.894 (4) ÅT = 100 K
β = 92.255 (6)°Needle, colourless
V = 926.3 (5) Å30.12 × 0.04 × 0.04 mm
Data collection top
Bruker APEX CCD
diffractometer
3762 independent reflections
Radiation source: microsource3371 reflections with I > 2σ(I)
Multilayer optics monochromatorRint = 0.069
ω scansθmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan
SADABS
h = 55
Tmin = 0.588, Tmax = 0.745k = 2020
10911 measured reflectionsl = 1414
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.045 w = 1/[σ2(Fo2) + (0.042P)2 + 0.6P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.099(Δ/σ)max = 0.014
S = 1.01Δρmax = 1.59 e Å3
3762 reflectionsΔρmin = 1.04 e Å3
235 parametersAbsolute structure: Flack x determined using 1417 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61).
30 restraintsAbsolute structure parameter: 0.03 (4)
Crystal data top
C9H23MnN3O7·2(I)V = 926.3 (5) Å3
Mr = 594.04Z = 2
Monoclinic, P21Mo Kα radiation
a = 4.7932 (16) ŵ = 4.08 mm1
b = 16.261 (5) ÅT = 100 K
c = 11.894 (4) Å0.12 × 0.04 × 0.04 mm
β = 92.255 (6)°
Data collection top
Bruker APEX CCD
diffractometer
3762 independent reflections
Absorption correction: multi-scan
SADABS
3371 reflections with I > 2σ(I)
Tmin = 0.588, Tmax = 0.745Rint = 0.069
10911 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.099Δρmax = 1.59 e Å3
S = 1.01Δρmin = 1.04 e Å3
3762 reflectionsAbsolute structure: Flack x determined using 1417 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61).
235 parametersAbsolute structure parameter: 0.03 (4)
30 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Mn10.9199 (5)0.74999 (13)0.06440 (18)0.0125 (4)
I10.76587 (17)0.37006 (5)0.31903 (7)0.0167 (2)
I20.61347 (18)0.64837 (5)0.46242 (7)0.0185 (2)
O1W1.167 (2)0.8625 (7)0.0408 (8)0.017 (2)
H2W1.23 (3)0.866 (11)0.108 (5)0.020*
H1W1.29 (2)0.838 (8)0.004 (11)0.020*
O10.2765 (19)0.6959 (5)0.1573 (8)0.016 (2)
O20.6941 (18)0.6409 (6)0.1214 (8)0.015 (2)
C10.450 (3)0.6381 (8)0.1546 (11)0.017 (3)
C20.357 (3)0.5515 (8)0.1927 (12)0.012 (3)
H20.51230.52510.23850.014*
C30.281 (4)0.4975 (9)0.0913 (12)0.024 (3)
H3A0.24150.44150.11670.035*
H3B0.43750.49630.04060.035*
H3C0.11560.52000.05130.035*
N10.737 (2)0.7153 (7)0.2601 (10)0.014 (2)
H1N0.894 (18)0.708 (9)0.214 (10)0.017*
H2N0.68 (3)0.768 (3)0.272 (12)0.017*
H3N0.75 (3)0.692 (9)0.330 (6)0.017*
O30.571 (2)0.7637 (6)0.0602 (8)0.0145 (19)
O40.1481 (19)0.7036 (6)0.0846 (7)0.0127 (19)
C40.396 (3)0.7169 (8)0.1107 (10)0.011 (3)
C50.498 (3)0.6700 (8)0.2133 (12)0.018 (3)
H50.34270.66740.27190.022*
C60.582 (3)0.5826 (8)0.1801 (12)0.019 (3)
H6A0.64730.55340.24610.028*
H6B0.42080.55380.15080.028*
H6C0.73260.58460.12190.028*
N20.107 (3)0.5610 (7)0.2631 (10)0.016 (2)
H4N0.03 (3)0.510 (4)0.268 (12)0.019*
H5N0.01 (3)0.599 (7)0.220 (10)0.019*
H6N0.14 (3)0.589 (8)0.329 (7)0.019*
O50.790 (2)0.8190 (6)0.1996 (8)0.018 (2)
O60.4015 (18)0.8845 (6)0.2518 (7)0.016 (2)
C70.644 (3)0.8565 (8)0.2698 (11)0.016 (3)
C80.771 (2)0.8721 (9)0.3869 (11)0.016 (3)
H80.63550.85660.44510.019*
C90.852 (3)0.9633 (9)0.3997 (13)0.024 (3)
H9A0.94080.97240.47430.035*
H9B0.68460.99750.39100.035*
H9C0.98350.97810.34180.035*
N31.028 (3)0.8214 (8)0.4007 (11)0.019 (3)
H7N1.07 (3)0.826 (10)0.477 (4)0.023*
H8N1.17 (2)0.842 (8)0.356 (11)0.023*
H9N1.01 (3)0.766 (2)0.392 (12)0.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0096 (9)0.0112 (10)0.0170 (10)0.0005 (8)0.0013 (7)0.0004 (8)
I10.0164 (5)0.0110 (4)0.0227 (5)0.0013 (4)0.0009 (3)0.0011 (4)
I20.0197 (5)0.0162 (4)0.0197 (5)0.0042 (4)0.0009 (3)0.0017 (4)
O1W0.017 (5)0.014 (5)0.020 (5)0.001 (5)0.001 (4)0.001 (5)
O10.013 (5)0.009 (5)0.026 (5)0.003 (4)0.004 (4)0.002 (4)
O20.011 (5)0.012 (5)0.023 (5)0.001 (4)0.003 (4)0.000 (4)
C10.018 (7)0.009 (7)0.023 (7)0.004 (6)0.003 (6)0.002 (6)
C20.005 (6)0.010 (7)0.021 (7)0.002 (5)0.005 (5)0.003 (5)
C30.035 (9)0.014 (8)0.021 (8)0.003 (7)0.003 (7)0.001 (6)
N10.010 (6)0.012 (6)0.020 (6)0.001 (5)0.004 (5)0.001 (5)
O30.012 (5)0.010 (4)0.021 (5)0.001 (4)0.000 (4)0.005 (4)
O40.012 (5)0.015 (5)0.012 (5)0.005 (4)0.003 (4)0.004 (4)
C40.009 (7)0.013 (7)0.011 (6)0.003 (5)0.003 (5)0.003 (5)
C50.012 (7)0.019 (8)0.023 (8)0.002 (6)0.002 (6)0.004 (6)
C60.020 (8)0.010 (7)0.026 (8)0.002 (6)0.002 (6)0.004 (6)
N20.017 (7)0.010 (6)0.020 (6)0.002 (5)0.001 (5)0.001 (5)
O50.013 (5)0.019 (5)0.022 (5)0.001 (4)0.005 (4)0.000 (4)
O60.012 (5)0.015 (5)0.020 (5)0.001 (4)0.002 (4)0.001 (4)
C70.011 (5)0.017 (6)0.020 (5)0.008 (4)0.003 (4)0.002 (5)
C80.008 (5)0.017 (5)0.023 (5)0.001 (5)0.001 (4)0.002 (5)
C90.029 (8)0.015 (7)0.025 (7)0.000 (6)0.013 (6)0.008 (6)
N30.018 (7)0.016 (6)0.022 (7)0.005 (5)0.005 (5)0.004 (5)
Geometric parameters (Å, º) top
Mn1—O52.077 (10)O4—C41.259 (15)
Mn1—O1i2.183 (9)O4—Mn1ii2.249 (9)
Mn1—O22.199 (10)C4—C51.536 (18)
Mn1—O32.202 (10)C5—C61.52 (2)
Mn1—O1W2.202 (11)C5—H51.0000
Mn1—O4i2.249 (9)C6—H6A0.9800
O1W—H2W0.84 (3)C6—H6B0.9800
O1W—H1W0.84 (3)C6—H6C0.9800
O1—C11.256 (16)N2—H4N0.92 (3)
O1—Mn1ii2.183 (9)N2—H5N0.92 (3)
O2—C11.252 (16)N2—H6N0.92 (3)
C1—C21.549 (18)O5—C71.268 (16)
C2—N21.496 (18)O6—C71.258 (16)
C2—C31.52 (2)C7—C81.520 (18)
C2—H21.0000C8—N31.485 (18)
C3—H3A0.9800C8—C91.54 (2)
C3—H3B0.9800C8—H81.0000
C3—H3C0.9800C9—H9A0.9800
N1—C51.488 (18)C9—H9B0.9800
N1—H1N0.92 (3)C9—H9C0.9800
N1—H2N0.91 (3)N3—H7N0.92 (3)
N1—H3N0.92 (3)N3—H8N0.92 (3)
O3—C41.265 (16)N3—H9N0.91 (3)
O5—Mn1—O1i94.5 (4)O4—C4—O3126.9 (12)
O5—Mn1—O291.8 (4)O4—C4—C5116.3 (11)
O1i—Mn1—O284.5 (3)O3—C4—C5116.8 (11)
O5—Mn1—O3103.0 (4)N1—C5—C6111.0 (12)
O1i—Mn1—O3160.1 (4)N1—C5—C4108.9 (11)
O2—Mn1—O385.4 (4)C6—C5—C4110.2 (11)
O5—Mn1—O1W80.1 (4)N1—C5—H5108.9
O1i—Mn1—O1W89.2 (4)C6—C5—H5108.9
O2—Mn1—O1W169.3 (4)C4—C5—H5108.9
O3—Mn1—O1W103.1 (4)C5—C6—H6A109.5
O5—Mn1—O4i164.0 (4)C5—C6—H6B109.5
O1i—Mn1—O4i82.4 (4)H6A—C6—H6B109.5
O2—Mn1—O4i103.5 (3)C5—C6—H6C109.5
O3—Mn1—O4i83.3 (3)H6A—C6—H6C109.5
O1W—Mn1—O4i84.1 (3)H6B—C6—H6C109.5
Mn1—O1W—H2W96 (10)C2—N2—H4N107 (9)
Mn1—O1W—H1W93 (10)C2—N2—H5N100 (9)
H2W—O1W—H1W108 (10)H4N—N2—H5N116 (10)
C1—O1—Mn1ii142.6 (9)C2—N2—H6N114 (9)
C1—O2—Mn1127.2 (9)H4N—N2—H6N117 (10)
O2—C1—O1127.5 (13)H5N—N2—H6N102 (10)
O2—C1—C2114.1 (12)C7—O5—Mn1163.8 (9)
O1—C1—C2118.4 (12)O6—C7—O5126.4 (12)
N2—C2—C3109.3 (12)O6—C7—C8115.5 (12)
N2—C2—C1108.3 (11)O5—C7—C8118.1 (12)
C3—C2—C1110.7 (11)N3—C8—C7108.1 (11)
N2—C2—H2109.5N3—C8—C9108.6 (11)
C3—C2—H2109.5C7—C8—C9109.9 (11)
C1—C2—H2109.5N3—C8—H8110.1
C2—C3—H3A109.5C7—C8—H8110.1
C2—C3—H3B109.5C9—C8—H8110.1
H3A—C3—H3B109.5C8—C9—H9A109.5
C2—C3—H3C109.5C8—C9—H9B109.5
H3A—C3—H3C109.5H9A—C9—H9B109.5
H3B—C3—H3C109.5C8—C9—H9C109.5
C5—N1—H1N110 (9)H9A—C9—H9C109.5
C5—N1—H2N107 (10)H9B—C9—H9C109.5
H1N—N1—H2N117 (10)C8—N3—H7N101 (10)
C5—N1—H3N103 (10)C8—N3—H8N110 (10)
H1N—N1—H3N113 (10)H7N—N3—H8N115 (10)
H2N—N1—H3N106 (10)C8—N3—H9N119 (10)
C4—O3—Mn1136.9 (9)H7N—N3—H9N102 (10)
C4—O4—Mn1ii129.0 (8)H8N—N3—H9N110 (10)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
(5) top
Crystal data top
C6H18CaN2O6·2(Cl)·H2OF(000) = 720
Mr = 343.22Dx = 1.518 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
a = 23.347 (7) ŵ = 0.80 mm1
b = 8.702 (3) ÅT = 100 K
c = 7.391 (2) ÅNeedle, colourless
V = 1501.5 (8) Å30.20 × 0.08 × 0.04 mm
Z = 4
Data collection top
Bruker APEX CCD
diffractometer
1545 independent reflections
Radiation source: microsource1164 reflections with I > 2σ(I)
Multi-layer optics monochromatorRint = 0.129
ω scansθmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan
SADABS
h = 2929
Tmin = 0.571, Tmax = 0.745k = 1010
16504 measured reflectionsl = 99
Refinement top
Refinement on F26 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.083 w = 1/[σ2(Fo2) + (0.025P)2 + 0.6P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.002
1545 reflectionsΔρmax = 0.34 e Å3
102 parametersΔρmin = 0.31 e Å3
Crystal data top
C6H18CaN2O6·2(Cl)·H2OV = 1501.5 (8) Å3
Mr = 343.22Z = 4
Orthorhombic, PbcnMo Kα radiation
a = 23.347 (7) ŵ = 0.80 mm1
b = 8.702 (3) ÅT = 100 K
c = 7.391 (2) Å0.20 × 0.08 × 0.04 mm
Data collection top
Bruker APEX CCD
diffractometer
1545 independent reflections
Absorption correction: multi-scan
SADABS
1164 reflections with I > 2σ(I)
Tmin = 0.571, Tmax = 0.745Rint = 0.129
16504 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0376 restraints
wR(F2) = 0.083H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.34 e Å3
1545 reflectionsΔρmin = 0.31 e Å3
102 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ca10.50000.59494 (8)0.25000.01290 (19)
Cl10.68892 (3)0.73248 (7)0.05715 (9)0.01771 (18)
O10.59104 (7)0.4699 (2)0.2517 (3)0.0224 (5)
O20.53781 (8)0.3579 (2)0.0429 (2)0.0208 (4)
C10.58538 (11)0.3843 (3)0.1180 (4)0.0160 (6)
C20.63906 (11)0.3070 (3)0.0425 (4)0.0164 (6)
H20.64270.33420.08850.020*
C30.63797 (12)0.1331 (3)0.0599 (4)0.0225 (6)
H3A0.67270.08990.00530.034*
H3B0.60420.09240.00250.034*
H3C0.63640.10470.18810.034*
N10.68928 (9)0.3709 (3)0.1413 (3)0.0165 (5)
H1A0.6865 (11)0.353 (3)0.264 (2)0.020*
H1B0.6908 (11)0.475 (2)0.125 (4)0.020*
H1C0.7220 (9)0.324 (3)0.096 (4)0.020*
O1W0.55648 (8)0.8059 (2)0.1368 (3)0.0250 (5)
H3E0.5900 (8)0.793 (3)0.117 (4)0.030*
H3D0.5480 (13)0.892 (2)0.175 (4)0.030*
O2W0.50001.0793 (3)0.25000.0352 (8)
H40.4958 (15)1.137 (3)0.160 (3)0.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ca10.0082 (4)0.0166 (4)0.0139 (4)0.0000.0001 (3)0.000
Cl10.0119 (3)0.0200 (3)0.0212 (4)0.0023 (3)0.0005 (3)0.0010 (3)
O10.0129 (10)0.0248 (10)0.0296 (12)0.0022 (8)0.0019 (9)0.0079 (9)
O20.0107 (10)0.0335 (11)0.0181 (10)0.0006 (8)0.0015 (8)0.0061 (9)
C10.0136 (14)0.0177 (13)0.0166 (14)0.0002 (11)0.0018 (11)0.0090 (11)
C20.0142 (14)0.0198 (14)0.0152 (14)0.0008 (10)0.0008 (11)0.0001 (11)
C30.0201 (15)0.0185 (14)0.0290 (17)0.0016 (11)0.0021 (13)0.0002 (13)
N10.0099 (11)0.0185 (12)0.0212 (13)0.0002 (9)0.0009 (11)0.0002 (11)
O1W0.0126 (10)0.0196 (10)0.0426 (14)0.0007 (9)0.0077 (10)0.0007 (10)
O2W0.055 (2)0.0203 (17)0.0306 (19)0.0000.0203 (18)0.000
Geometric parameters (Å, º) top
Ca1—O2i2.3732 (19)O2—Ca1ii2.3732 (19)
Ca1—O2ii2.3732 (19)C1—C21.528 (4)
Ca1—O1iii2.3880 (18)C2—N11.489 (3)
Ca1—O12.3880 (18)C2—C31.519 (3)
Ca1—O1W2.410 (2)C2—H21.0000
Ca1—O1Wiii2.410 (2)C3—H3A0.9800
Ca1—O22.716 (2)C3—H3B0.9800
Ca1—O2iii2.716 (2)C3—H3C0.9800
Ca1—C1iii2.879 (3)N1—H1A0.922 (17)
Ca1—C12.879 (3)N1—H1B0.917 (17)
Ca1—Ca1ii4.0479 (12)N1—H1C0.927 (17)
Ca1—Ca1iv4.0479 (12)O1W—H3E0.805 (17)
O1—C11.245 (3)O1W—H3D0.825 (17)
O2—C11.263 (3)O2W—H40.840 (17)
O2i—Ca1—O2ii160.10 (10)O1W—Ca1—Ca1ii89.66 (6)
O2i—Ca1—O1iii114.50 (7)O1Wiii—Ca1—Ca1ii128.89 (6)
O2ii—Ca1—O1iii75.10 (6)O2—Ca1—Ca1ii34.46 (4)
O2i—Ca1—O175.10 (6)O2iii—Ca1—Ca1ii101.81 (5)
O2ii—Ca1—O1114.50 (7)C1iii—Ca1—Ca1ii92.83 (6)
O1iii—Ca1—O1125.78 (9)C1—Ca1—Ca1ii55.29 (6)
O2i—Ca1—O1W88.93 (7)O2i—Ca1—Ca1iv40.36 (5)
O2ii—Ca1—O1W75.84 (7)O2ii—Ca1—Ca1iv154.57 (5)
O1iii—Ca1—O1W146.33 (7)O1iii—Ca1—Ca1iv79.56 (5)
O1—Ca1—O1W82.07 (7)O1—Ca1—Ca1iv79.00 (5)
O2i—Ca1—O1Wiii75.84 (7)O1W—Ca1—Ca1iv128.89 (6)
O2ii—Ca1—O1Wiii88.93 (7)O1Wiii—Ca1—Ca1iv89.66 (6)
O1iii—Ca1—O1Wiii82.07 (7)O2—Ca1—Ca1iv101.81 (5)
O1—Ca1—O1Wiii146.33 (7)O2iii—Ca1—Ca1iv34.46 (4)
O1W—Ca1—O1Wiii80.77 (10)C1iii—Ca1—Ca1iv55.29 (6)
O2i—Ca1—O2121.63 (6)C1—Ca1—Ca1iv92.83 (6)
O2ii—Ca1—O274.81 (7)Ca1ii—Ca1—Ca1iv131.82 (4)
O1iii—Ca1—O286.58 (6)C1—O1—Ca1100.03 (16)
O1—Ca1—O250.77 (6)C1—O2—Ca1ii134.18 (17)
O1W—Ca1—O2101.83 (7)C1—O2—Ca184.27 (16)
O1Wiii—Ca1—O2162.15 (7)Ca1ii—O2—Ca1105.19 (7)
O2i—Ca1—O2iii74.81 (7)O1—C1—O2123.5 (2)
O2ii—Ca1—O2iii121.63 (6)O1—C1—C2117.8 (2)
O1iii—Ca1—O2iii50.77 (6)O2—C1—C2118.8 (2)
O1—Ca1—O2iii86.58 (6)O1—C1—Ca154.78 (13)
O1W—Ca1—O2iii162.15 (7)O2—C1—Ca169.85 (15)
O1Wiii—Ca1—O2iii101.83 (7)C2—C1—Ca1166.44 (18)
O2—Ca1—O2iii81.18 (8)N1—C2—C3110.1 (2)
O2i—Ca1—C1iii93.36 (7)N1—C2—C1107.6 (2)
O2ii—Ca1—C1iii99.30 (7)C3—C2—C1113.2 (2)
O1iii—Ca1—C1iii25.20 (7)N1—C2—H2108.6
O1—Ca1—C1iii108.93 (8)C3—C2—H2108.6
O1W—Ca1—C1iii168.99 (7)C1—C2—H2108.6
O1Wiii—Ca1—C1iii89.35 (7)C2—C3—H3A109.5
O2—Ca1—C1iii86.13 (7)C2—C3—H3B109.5
O2iii—Ca1—C1iii25.88 (6)H3A—C3—H3B109.5
O2i—Ca1—C199.30 (7)C2—C3—H3C109.5
O2ii—Ca1—C193.36 (7)H3A—C3—H3C109.5
O1iii—Ca1—C1108.93 (8)H3B—C3—H3C109.5
O1—Ca1—C125.20 (7)C2—N1—H1A111.4 (17)
O1W—Ca1—C189.35 (7)C2—N1—H1B109.5 (16)
O1Wiii—Ca1—C1168.99 (7)H1A—N1—H1B107 (2)
O2—Ca1—C125.88 (6)C2—N1—H1C107.9 (18)
O2iii—Ca1—C186.13 (7)H1A—N1—H1C110 (2)
C1iii—Ca1—C1100.88 (11)H1B—N1—H1C111 (2)
O2i—Ca1—Ca1ii154.57 (5)Ca1—O1W—H3E119 (2)
O2ii—Ca1—Ca1ii40.36 (5)Ca1—O1W—H3D116 (2)
O1iii—Ca1—Ca1ii79.00 (5)H3E—O1W—H3D115 (3)
O1—Ca1—Ca1ii79.56 (5)
Symmetry codes: (i) x, y+1, z+1/2; (ii) x+1, y+1, z; (iii) x+1, y, z+1/2; (iv) x+1, y+1, z+1.
(6) top
Crystal data top
C9H23CaN3O7·2(Br)F(000) = 976
Mr = 485.20Dx = 1.779 Mg m3
Orthorhombic, Pc21nMo Kα radiation, λ = 0.71073 Å
a = 4.8727 (5) ŵ = 4.79 mm1
b = 16.0701 (17) ÅT = 100 K
c = 23.129 (2) ÅNeedle, colourless
V = 1811.1 (3) Å30.50 × 0.09 × 0.07 mm
Z = 4
Data collection top
Bruker APEX CCD
diffractometer
3739 independent reflections
Radiation source: microsource3450 reflections with I > 2σ(I)
Multilayer optics monochromatorRint = 0.060
ω scansθmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)
h = 66
Tmin = 0.437, Tmax = 0.745k = 2020
20251 measured reflectionsl = 2928
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.028 w = 1/[σ2(Fo2) + (0.020P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.062(Δ/σ)max < 0.001
S = 1.03Δρmax = 1.06 e Å3
3739 reflectionsΔρmin = 0.30 e Å3
234 parametersAbsolute structure: Flack x determined using 1545 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61).
38 restraintsAbsolute structure parameter: 0.004 (6)
Crystal data top
C9H23CaN3O7·2(Br)V = 1811.1 (3) Å3
Mr = 485.20Z = 4
Orthorhombic, Pc21nMo Kα radiation
a = 4.8727 (5) ŵ = 4.79 mm1
b = 16.0701 (17) ÅT = 100 K
c = 23.129 (2) Å0.50 × 0.09 × 0.07 mm
Data collection top
Bruker APEX CCD
diffractometer
3739 independent reflections
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)
3450 reflections with I > 2σ(I)
Tmin = 0.437, Tmax = 0.745Rint = 0.060
20251 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.062Δρmax = 1.06 e Å3
S = 1.03Δρmin = 0.30 e Å3
3739 reflectionsAbsolute structure: Flack x determined using 1545 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61).
234 parametersAbsolute structure parameter: 0.004 (6)
38 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ca10.9085 (2)0.75000 (6)0.03355 (4)0.0096 (2)
Br10.57417 (12)0.65284 (4)0.23125 (2)0.02133 (15)
Br20.75563 (10)0.36823 (4)0.16347 (2)0.01238 (12)
O50.7433 (7)0.8303 (2)0.10495 (16)0.0144 (8)
O60.3528 (7)0.8887 (2)0.13480 (16)0.0137 (8)
O1W1.1826 (7)0.8715 (3)0.02281 (15)0.0133 (8)
H1W1.237 (11)0.878 (4)0.0532 (19)0.016*
H2W1.314 (9)0.859 (4)0.008 (2)0.016*
N30.9651 (10)0.8216 (3)0.2085 (2)0.0139 (10)
H9N1.082 (10)0.834 (4)0.1796 (19)0.017*
H7N1.045 (12)0.830 (4)0.2435 (15)0.017*
H8N0.925 (12)0.7672 (19)0.210 (3)0.017*
C90.7680 (13)0.9621 (4)0.2169 (3)0.0200 (13)
H9C0.89260.98460.18760.024*
H9A0.85380.96640.25510.024*
H9B0.59610.99370.21660.024*
C80.7081 (10)0.8714 (4)0.2036 (2)0.0131 (10)
H8A0.57110.84990.23220.016*
C70.5909 (10)0.8621 (3)0.1428 (2)0.0126 (11)
O40.1499 (8)0.7049 (2)0.05102 (16)0.0135 (8)
O30.5612 (7)0.7625 (2)0.03518 (15)0.0123 (8)
C40.3979 (11)0.7181 (3)0.0636 (2)0.0106 (11)
C50.5094 (11)0.6740 (3)0.1170 (2)0.0114 (11)
H5A0.36340.67180.14740.014*
C60.5979 (13)0.5859 (4)0.1017 (3)0.0198 (13)
H6C0.73630.58790.07100.024*
H6A0.67590.55900.13600.024*
H6B0.43840.55420.08830.024*
N20.7484 (9)0.7226 (3)0.1392 (2)0.0118 (10)
H5N0.792 (11)0.700 (4)0.1735 (16)0.014*
H6N0.724 (11)0.7780 (18)0.142 (3)0.014*
H4N0.881 (9)0.718 (4)0.113 (2)0.014*
N10.0739 (10)0.5555 (3)0.1412 (2)0.0134 (10)
H2N0.062 (9)0.578 (3)0.120 (2)0.016*
H3N0.015 (11)0.510 (3)0.153 (2)0.016*
H1N0.095 (12)0.591 (3)0.1719 (18)0.016*
C10.4265 (12)0.6279 (3)0.0851 (2)0.0122 (11)
C20.3281 (11)0.5436 (3)0.1058 (2)0.0116 (11)
H2A0.47360.51700.13000.014*
C30.2614 (13)0.4877 (4)0.0546 (3)0.0215 (13)
H3A0.19860.43340.06870.032*
H3B0.42610.48020.03080.032*
H3C0.11640.51340.03130.032*
O10.2600 (7)0.6863 (2)0.08266 (16)0.0133 (8)
O20.6762 (7)0.6311 (2)0.06906 (16)0.0137 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ca10.0092 (5)0.0100 (5)0.0097 (5)0.0005 (4)0.0002 (4)0.0002 (4)
Br10.0315 (3)0.0188 (3)0.0137 (3)0.0106 (3)0.0023 (2)0.0011 (2)
Br20.0130 (2)0.0112 (2)0.0130 (2)0.0009 (2)0.0007 (2)0.0008 (2)
O50.012 (2)0.0183 (19)0.0125 (19)0.0013 (16)0.0015 (16)0.0042 (16)
O60.0122 (19)0.014 (2)0.0153 (19)0.0006 (15)0.0012 (16)0.0010 (15)
O1W0.012 (2)0.0174 (19)0.0102 (18)0.0015 (19)0.0001 (14)0.001 (2)
N30.013 (3)0.016 (2)0.012 (2)0.001 (2)0.002 (2)0.001 (2)
C90.025 (4)0.015 (3)0.020 (3)0.000 (2)0.006 (3)0.006 (2)
C80.012 (3)0.015 (3)0.012 (2)0.001 (3)0.000 (2)0.002 (3)
C70.014 (3)0.010 (2)0.013 (3)0.003 (3)0.003 (2)0.000 (2)
O40.010 (2)0.018 (2)0.0126 (19)0.0009 (15)0.0006 (16)0.0019 (15)
O30.012 (2)0.0126 (19)0.0117 (18)0.0007 (16)0.0012 (16)0.0010 (15)
C40.010 (3)0.010 (2)0.012 (3)0.004 (2)0.000 (2)0.003 (2)
C50.007 (3)0.015 (3)0.012 (2)0.0006 (19)0.002 (2)0.003 (2)
C60.021 (3)0.011 (3)0.027 (3)0.001 (2)0.007 (3)0.005 (2)
N20.012 (3)0.014 (2)0.009 (2)0.000 (2)0.0017 (19)0.0019 (19)
N10.012 (2)0.013 (2)0.015 (2)0.002 (2)0.003 (2)0.0030 (19)
C10.011 (3)0.016 (3)0.010 (2)0.003 (2)0.004 (2)0.003 (2)
C20.005 (3)0.010 (3)0.019 (3)0.000 (2)0.000 (2)0.002 (2)
C30.025 (4)0.018 (3)0.020 (3)0.005 (3)0.002 (3)0.004 (3)
O10.0090 (19)0.0127 (19)0.018 (2)0.0012 (15)0.0039 (16)0.0032 (15)
O20.0089 (19)0.015 (2)0.0173 (19)0.0008 (14)0.0015 (15)0.0046 (16)
Geometric parameters (Å, º) top
Ca1—O52.245 (4)O3—C41.254 (6)
Ca1—O1i2.296 (4)C4—C51.524 (7)
Ca1—O32.331 (4)C5—N21.493 (7)
Ca1—O22.367 (4)C5—C61.521 (8)
Ca1—O1W2.379 (4)C5—H5A1.0000
Ca1—O4i2.395 (4)C6—H6C0.9800
Ca1—H1W2.64 (6)C6—H6A0.9800
Ca1—H2W2.71 (6)C6—H6B0.9800
O5—C71.257 (6)N2—H5N0.90 (3)
O6—C71.250 (6)N2—H6N0.90 (3)
O1W—H1W0.76 (4)N2—H4N0.89 (3)
O1W—H2W0.75 (4)N1—C21.497 (7)
N3—C81.491 (7)N1—H2N0.90 (3)
N3—H9N0.90 (3)N1—H3N0.90 (3)
N3—H7N0.91 (3)N1—H1N0.91 (3)
N3—H8N0.90 (3)C1—O11.242 (7)
C9—C81.518 (8)C1—O21.273 (7)
C9—H9C0.9800C1—C21.515 (7)
C9—H9A0.9800C2—C31.522 (8)
C9—H9B0.9800C2—H2A1.0000
C8—C71.526 (7)C3—H3A0.9800
C8—H8A1.0000C3—H3B0.9800
O4—C41.261 (6)C3—H3C0.9800
O4—Ca1ii2.395 (4)O1—Ca1ii2.296 (4)
O5—Ca1—O1i99.20 (14)O6—C7—O5125.8 (5)
O5—Ca1—O3101.06 (13)O6—C7—C8116.8 (4)
O1i—Ca1—O3156.57 (14)O5—C7—C8117.4 (4)
O5—Ca1—O292.13 (14)C4—O4—Ca1ii127.4 (3)
O1i—Ca1—O279.94 (13)C4—O3—Ca1140.3 (3)
O3—Ca1—O287.64 (13)O3—C4—O4125.7 (5)
O5—Ca1—O1W78.83 (14)O3—C4—C5117.6 (5)
O1i—Ca1—O1W89.93 (14)O4—C4—C5116.8 (5)
O3—Ca1—O1W105.43 (13)N2—C5—C6110.2 (4)
O2—Ca1—O1W165.24 (13)N2—C5—C4108.3 (4)
O5—Ca1—O4i161.98 (14)C6—C5—C4110.2 (4)
O1i—Ca1—O4i84.41 (13)N2—C5—H5A109.4
O3—Ca1—O4i79.97 (13)C6—C5—H5A109.4
O2—Ca1—O4i105.90 (13)C4—C5—H5A109.4
O1W—Ca1—O4i83.54 (13)C5—C6—H6C109.5
O5—Ca1—H1W69.1 (12)C5—C6—H6A109.5
O1i—Ca1—H1W79.1 (13)H6C—C6—H6A109.5
O3—Ca1—H1W119.3 (12)C5—C6—H6B109.5
O2—Ca1—H1W149.0 (10)H6C—C6—H6B109.5
O1W—Ca1—H1W16.3 (10)H6A—C6—H6B109.5
O4i—Ca1—H1W94.5 (12)C5—N2—H5N106 (4)
O5—Ca1—H2W92.9 (11)C5—N2—H6N116 (4)
O1i—Ca1—H2W81.6 (13)H5N—N2—H6N111 (6)
O3—Ca1—H2W108.9 (13)C5—N2—H4N107 (4)
O2—Ca1—H2W161.4 (12)H5N—N2—H4N113 (5)
O1W—Ca1—H2W15.3 (11)H6N—N2—H4N104 (5)
O4i—Ca1—H2W70.0 (11)C2—N1—H2N111 (4)
H1W—Ca1—H2W24.9 (17)C2—N1—H3N117 (4)
C7—O5—Ca1163.4 (4)H2N—N1—H3N98 (5)
Ca1—O1W—H1W102 (5)C2—N1—H1N114 (4)
Ca1—O1W—H2W108 (5)H2N—N1—H1N105 (5)
H1W—O1W—H2W100 (6)H3N—N1—H1N109 (5)
C8—N3—H9N111 (4)O1—C1—O2125.5 (5)
C8—N3—H7N111 (4)O1—C1—C2118.9 (5)
H9N—N3—H7N111 (6)O2—C1—C2115.5 (5)
C8—N3—H8N110 (4)N1—C2—C1108.7 (4)
H9N—N3—H8N113 (5)N1—C2—C3108.9 (4)
H7N—N3—H8N101 (5)C1—C2—C3110.5 (5)
C8—C9—H9C109.5N1—C2—H2A109.6
C8—C9—H9A109.5C1—C2—H2A109.6
H9C—C9—H9A109.5C3—C2—H2A109.6
C8—C9—H9B109.5C2—C3—H3A109.5
H9C—C9—H9B109.5C2—C3—H3B109.5
H9A—C9—H9B109.5H3A—C3—H3B109.5
N3—C8—C9109.8 (4)C2—C3—H3C109.5
N3—C8—C7109.4 (4)H3A—C3—H3C109.5
C9—C8—C7110.6 (5)H3B—C3—H3C109.5
N3—C8—H8A109.0C1—O1—Ca1ii147.9 (3)
C9—C8—H8A109.0C1—O2—Ca1126.2 (3)
C7—C8—H8A109.0
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
(7) top
Crystal data top
C15H41Ca2N5O13·4(I)·2(H2O)Z = 4
Mr = 1123.32F(000) = 2168
Monoclinic, P21/cDx = 2.096 Mg m3
a = 22.842 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.3609 (13) ŵ = 3.85 mm1
c = 18.807 (3) ÅT = 100 K
β = 97.734 (3)°Needle, colourless
V = 3559.1 (10) Å30.18 × 0.06 × 0.05 mm
Data collection top
Bruker APEX CCD
diffractometer
7339 independent reflections
Radiation source: microsource5475 reflections with I > 2σ(I)
Multilayer optics monochromatorRint = 0.103
ω scansθmax = 26.5°, θmin = 0.9°
Absorption correction: multi-scan
SADABS
h = 2828
Tmin = 0.570, Tmax = 0.755k = 1010
41724 measured reflectionsl = 2323
Refinement top
Refinement on F215 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.101 w = 1/[σ2(Fo2) + (0.030P)2 + 1.P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
7339 reflectionsΔρmax = 2.00 e Å3
420 parametersΔρmin = 1.46 e Å3
Crystal data top
C15H41Ca2N5O13·4(I)·2(H2O)V = 3559.1 (10) Å3
Mr = 1123.32Z = 4
Monoclinic, P21/cMo Kα radiation
a = 22.842 (4) ŵ = 3.85 mm1
b = 8.3609 (13) ÅT = 100 K
c = 18.807 (3) Å0.18 × 0.06 × 0.05 mm
β = 97.734 (3)°
Data collection top
Bruker APEX CCD
diffractometer
7339 independent reflections
Absorption correction: multi-scan
SADABS
5475 reflections with I > 2σ(I)
Tmin = 0.570, Tmax = 0.755Rint = 0.103
41724 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04615 restraints
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 2.00 e Å3
7339 reflectionsΔρmin = 1.46 e Å3
420 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.56851 (2)0.72857 (5)0.65183 (2)0.01631 (12)
I20.57243 (2)0.67891 (5)0.90174 (2)0.01641 (12)
I30.94569 (2)0.78083 (6)0.84436 (2)0.01830 (12)
I40.92274 (2)0.70133 (6)0.60187 (3)0.02210 (12)
Ca10.74407 (5)0.18112 (15)0.87017 (7)0.0102 (3)
Ca20.74623 (5)0.14511 (16)0.62740 (7)0.0112 (3)
O10.65489 (18)0.1027 (5)0.6691 (2)0.0155 (10)
O20.67798 (18)0.0319 (5)0.7843 (2)0.0114 (10)
C10.6428 (3)0.0827 (7)0.7322 (3)0.0092 (13)
C210.5805 (3)0.1316 (8)0.7443 (3)0.0123 (14)
H210.55150.08450.70540.015*
C310.5728 (3)0.3104 (8)0.7442 (4)0.0176 (15)
H31A0.60150.35780.78170.026*
H31B0.53270.33650.75360.026*
H31C0.57900.35340.69740.026*
N10.5690 (2)0.0647 (7)0.8150 (3)0.0144 (12)
H1A0.5342 (17)0.101 (8)0.828 (3)0.017*
H1B0.597 (2)0.109 (7)0.849 (3)0.017*
H1C0.567 (3)0.042 (3)0.806 (4)0.017*
O30.7303 (2)0.4169 (5)0.6533 (3)0.0193 (11)
O40.7239 (2)0.3555 (5)0.7678 (2)0.0171 (11)
C40.7256 (3)0.4535 (8)0.7174 (4)0.0120 (14)
C510.7267 (3)0.6332 (8)0.7358 (3)0.0128 (14)
H510.70820.69570.69330.015*
C60.7906 (3)0.6847 (8)0.7556 (4)0.0178 (15)
H6A0.80910.61960.79580.027*
H6B0.79190.79760.76960.027*
H6C0.81190.67000.71420.027*
N20.6932 (2)0.6602 (7)0.7979 (3)0.0157 (13)
H2A0.702 (3)0.589 (7)0.835 (3)0.024*
H2B0.6532 (11)0.652 (8)0.781 (3)0.024*
H2C0.701 (3)0.757 (5)0.822 (3)0.024*
O50.81341 (19)0.0801 (5)0.7249 (2)0.0150 (10)
O60.83890 (19)0.1560 (6)0.8381 (2)0.0208 (11)
C70.8493 (3)0.1333 (8)0.7746 (3)0.0137 (14)
C80.9106 (3)0.1805 (8)0.7590 (4)0.0180 (16)
H80.94050.14960.80060.022*
C90.9122 (4)0.3603 (9)0.7485 (5)0.033 (2)
H9A0.88560.38970.70510.050*
H9B0.95260.39360.74340.050*
H9C0.89950.41390.79020.050*
N30.9235 (2)0.0956 (7)0.6937 (3)0.0158 (13)
H3A0.899 (2)0.119 (8)0.653 (2)0.019*
H3B0.919 (3)0.013 (3)0.700 (4)0.019*
H3C0.9596 (16)0.109 (8)0.678 (3)0.019*
O70.80765 (19)0.3368 (5)0.4822 (2)0.0158 (10)
O80.83607 (18)0.1996 (5)0.5826 (2)0.0147 (10)
C100.6444 (3)0.2134 (8)0.4760 (4)0.0129 (14)
C110.5822 (3)0.2203 (8)0.4946 (3)0.0118 (14)
H110.55380.20410.44990.014*
C120.5705 (3)0.3822 (9)0.5265 (4)0.0213 (17)
H12A0.59790.39870.57070.032*
H12B0.52980.38570.53760.032*
H12C0.57620.46660.49200.032*
N40.5729 (2)0.0928 (7)0.5467 (3)0.0139 (12)
H4A0.576 (3)0.009 (4)0.530 (3)0.017*
H4B0.5378 (17)0.097 (8)0.566 (3)0.017*
H4C0.599 (2)0.104 (8)0.588 (2)0.017*
O90.65355 (19)0.2840 (5)0.4195 (2)0.0155 (10)
O100.68299 (18)0.1427 (5)0.5188 (2)0.0130 (10)
C130.8450 (3)0.2738 (8)0.5270 (4)0.0125 (14)
C140.9102 (3)0.2781 (7)0.5145 (3)0.0116 (14)
H140.93550.30300.56080.014*
C150.9296 (3)0.1189 (8)0.4858 (4)0.0249 (18)
H15A0.97160.12410.48030.037*
H15B0.90640.09710.43900.037*
H15C0.92320.03320.51940.037*
N50.9182 (2)0.4066 (7)0.4607 (3)0.0149 (13)
H5A0.9559 (14)0.395 (8)0.450 (3)0.018*
H5B0.917 (3)0.506 (4)0.481 (3)0.018*
H5C0.894 (2)0.385 (8)0.419 (2)0.018*
O1W0.8337 (2)0.7023 (6)0.9426 (2)0.0208 (11)
H1W0.86390.72340.91620.025*
H2W0.85730.72770.98470.025*
O2W0.6958 (2)0.3676 (6)0.5441 (2)0.0203 (11)
H4W0.70730.43940.58050.024*
H3W0.65670.33250.54620.024*
O3W0.7674 (2)0.1157 (5)0.5881 (2)0.0208 (11)
H5W0.74300.20020.57340.025*
H6W0.80460.15950.59140.025*
O4W0.7501 (2)0.4650 (5)0.9161 (2)0.0183 (11)
H7W0.77800.54460.92520.022*
H8W0.72790.42940.95060.022*
O5W0.73759 (18)0.0974 (5)0.9098 (2)0.0140 (10)
H9W0.76950.16430.92040.017*
H10W0.72370.10920.95320.017*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0147 (2)0.0159 (2)0.0186 (3)0.00246 (18)0.00305 (18)0.00132 (19)
I20.0167 (2)0.0167 (2)0.0171 (3)0.00184 (18)0.00670 (18)0.00420 (19)
I30.0135 (2)0.0228 (3)0.0193 (3)0.00161 (18)0.00484 (18)0.0049 (2)
I40.0335 (3)0.0172 (3)0.0154 (3)0.0019 (2)0.0026 (2)0.0007 (2)
Ca10.0107 (6)0.0129 (7)0.0071 (7)0.0020 (5)0.0013 (5)0.0000 (5)
Ca20.0123 (7)0.0135 (7)0.0083 (7)0.0016 (5)0.0025 (5)0.0008 (5)
O10.011 (2)0.024 (3)0.011 (3)0.0035 (19)0.0008 (19)0.002 (2)
O20.010 (2)0.012 (2)0.012 (2)0.0007 (18)0.0013 (18)0.0014 (19)
C10.014 (3)0.006 (3)0.008 (3)0.005 (2)0.004 (3)0.004 (2)
C210.014 (3)0.018 (4)0.005 (3)0.001 (3)0.003 (3)0.000 (3)
C310.019 (4)0.021 (4)0.014 (4)0.005 (3)0.008 (3)0.001 (3)
N10.010 (3)0.017 (3)0.016 (3)0.003 (2)0.005 (2)0.002 (3)
O30.024 (3)0.018 (3)0.018 (3)0.002 (2)0.010 (2)0.000 (2)
O40.023 (3)0.013 (3)0.015 (3)0.002 (2)0.002 (2)0.001 (2)
C40.010 (3)0.011 (3)0.015 (4)0.001 (3)0.004 (3)0.003 (3)
C510.019 (4)0.012 (3)0.007 (3)0.002 (3)0.003 (3)0.003 (3)
C60.012 (3)0.019 (4)0.023 (4)0.001 (3)0.004 (3)0.004 (3)
N20.015 (3)0.018 (3)0.015 (3)0.002 (3)0.003 (2)0.005 (2)
O50.014 (2)0.022 (3)0.008 (2)0.003 (2)0.0003 (19)0.003 (2)
O60.016 (3)0.037 (3)0.010 (3)0.001 (2)0.003 (2)0.001 (2)
C70.010 (3)0.021 (4)0.011 (4)0.003 (3)0.005 (3)0.000 (3)
C80.013 (3)0.026 (4)0.015 (4)0.002 (3)0.002 (3)0.006 (3)
C90.036 (5)0.025 (5)0.040 (5)0.006 (4)0.014 (4)0.005 (4)
N30.010 (3)0.021 (3)0.017 (3)0.003 (3)0.005 (2)0.000 (3)
O70.013 (2)0.022 (3)0.011 (3)0.003 (2)0.0014 (19)0.000 (2)
O80.013 (2)0.019 (3)0.013 (3)0.0019 (19)0.0033 (19)0.002 (2)
C100.013 (3)0.012 (3)0.014 (4)0.002 (3)0.005 (3)0.003 (3)
C110.009 (3)0.018 (4)0.008 (3)0.002 (3)0.002 (3)0.003 (3)
C120.016 (4)0.025 (4)0.025 (4)0.004 (3)0.009 (3)0.001 (3)
N40.010 (3)0.018 (3)0.014 (3)0.000 (2)0.003 (2)0.001 (3)
O90.017 (2)0.018 (3)0.012 (3)0.002 (2)0.0053 (19)0.004 (2)
O100.011 (2)0.018 (3)0.010 (2)0.0033 (19)0.0008 (18)0.0026 (19)
C130.014 (3)0.009 (3)0.014 (4)0.000 (3)0.001 (3)0.006 (3)
C140.011 (3)0.013 (3)0.009 (4)0.003 (3)0.004 (3)0.000 (3)
C150.026 (4)0.018 (4)0.034 (5)0.004 (3)0.017 (3)0.002 (3)
N50.012 (3)0.017 (3)0.015 (3)0.005 (3)0.001 (2)0.001 (3)
O1W0.019 (3)0.029 (3)0.015 (3)0.004 (2)0.003 (2)0.001 (2)
O2W0.016 (3)0.026 (3)0.019 (3)0.001 (2)0.004 (2)0.003 (2)
O3W0.022 (3)0.016 (3)0.024 (3)0.002 (2)0.001 (2)0.003 (2)
O4W0.022 (3)0.016 (3)0.018 (3)0.009 (2)0.005 (2)0.001 (2)
O5W0.019 (2)0.017 (3)0.007 (2)0.0035 (19)0.0017 (19)0.0032 (19)
Geometric parameters (Å, º) top
Ca1—O62.335 (5)C8—N31.482 (9)
Ca1—O9i2.395 (5)C8—C91.518 (10)
Ca1—O7i2.398 (4)C8—H81.0000
Ca1—O22.405 (4)C9—H9A0.9800
Ca1—O42.410 (5)C9—H9B0.9800
Ca1—O5W2.456 (4)C9—H9C0.9800
Ca1—O4W2.523 (5)N3—H3A0.92 (2)
Ca1—C73.214 (6)N3—H3B0.92 (2)
Ca1—H8W2.6233N3—H3C0.92 (2)
Ca2—O52.292 (4)O7—C131.233 (7)
Ca2—O102.338 (4)O8—C131.255 (8)
Ca2—O12.353 (4)C10—O101.258 (7)
Ca2—O32.362 (5)C10—O91.258 (8)
Ca2—O82.365 (4)C10—C111.509 (8)
Ca2—O3W2.373 (5)C11—N41.482 (8)
Ca2—C43.155 (6)C11—C121.519 (9)
O1—C11.264 (7)C11—H111.0000
O2—C11.255 (7)C12—H12A0.9800
C1—C211.528 (8)C12—H12B0.9800
C21—N11.498 (8)C12—H12C0.9800
C21—C311.506 (9)N4—H4A0.91 (2)
C21—H211.0000N4—H4B0.92 (2)
C31—H31A0.9800N4—H4C0.92 (2)
C31—H31B0.9800C13—C141.541 (9)
C31—H31C0.9800C14—N51.503 (8)
N1—H1A0.92 (2)C14—C151.525 (9)
N1—H1B0.92 (2)C14—H141.0000
N1—H1C0.91 (2)C15—H15A0.9800
O3—C41.264 (8)C15—H15B0.9800
O4—C41.257 (8)C15—H15C0.9800
C4—C511.541 (9)N5—H5A0.91 (2)
C51—N21.498 (8)N5—H5B0.92 (2)
C51—C61.518 (9)N5—H5C0.91 (2)
C51—H511.0000O1W—H1W0.9200
C6—H6A0.9800O1W—H2W0.9200
C6—H6B0.9800O2W—H4W0.9222
C6—H6C0.9800O2W—H3W0.9464
N2—H2A0.92 (2)O3W—H5W0.9200
N2—H2B0.93 (2)O3W—H6W0.9200
N2—H2C0.93 (2)O4W—H7W0.9206
O5—C71.239 (7)O4W—H8W0.9255
O6—C71.263 (8)O5W—H9W0.9200
C7—C81.522 (9)O5W—H10W0.9200
O6—Ca1—O9i172.01 (16)C51—C6—H6B109.5
O6—Ca1—O7i75.43 (16)H6A—C6—H6B109.5
O9i—Ca1—O7i96.88 (16)C51—C6—H6C109.5
O6—Ca1—O2107.47 (16)H6A—C6—H6C109.5
O9i—Ca1—O279.99 (15)H6B—C6—H6C109.5
O7i—Ca1—O2143.97 (16)C51—N2—H2A115 (4)
O6—Ca1—O486.12 (16)C51—N2—H2B107 (4)
O9i—Ca1—O498.81 (16)H2A—N2—H2B108 (6)
O7i—Ca1—O4140.20 (16)C51—N2—H2C116 (5)
O2—Ca1—O475.05 (15)H2A—N2—H2C100 (6)
O6—Ca1—O5W95.11 (17)H2B—N2—H2C110 (6)
O9i—Ca1—O5W84.69 (15)C7—O5—Ca2145.2 (5)
O7i—Ca1—O5W74.23 (15)C7—O6—Ca1123.8 (4)
O2—Ca1—O5W69.74 (14)O5—C7—O6125.3 (6)
O4—Ca1—O5W143.44 (15)O5—C7—C8118.7 (6)
O6—Ca1—O4W99.37 (17)O6—C7—C8115.9 (6)
O9i—Ca1—O4W76.33 (15)O5—C7—Ca189.9 (4)
O7i—Ca1—O4W76.07 (15)C8—C7—Ca1148.4 (4)
O2—Ca1—O4W135.90 (15)N3—C8—C9110.8 (6)
O4—Ca1—O4W72.54 (15)N3—C8—C7109.0 (5)
O5W—Ca1—O4W142.30 (15)C9—C8—C7108.7 (6)
O6—Ca1—C719.06 (16)N3—C8—H8109.4
O9i—Ca1—C7168.84 (16)C9—C8—H8109.4
O7i—Ca1—C794.24 (16)C7—C8—H8109.4
O2—Ca1—C790.51 (16)C8—C9—H9A109.5
O4—Ca1—C772.87 (16)C8—C9—H9B109.5
O5W—Ca1—C797.58 (16)H9A—C9—H9B109.5
O4W—Ca1—C7107.32 (17)C8—C9—H9C109.5
O6—Ca1—H8W115.3H9A—C9—H9C109.5
O9i—Ca1—H8W59.0H9B—C9—H9C109.5
O7i—Ca1—H8W70.0C8—N3—H3A115 (4)
O2—Ca1—H8W132.3C8—N3—H3B109 (4)
O4—Ca1—H8W87.4H3A—N3—H3B104 (6)
O5W—Ca1—H8W123.8C8—N3—H3C119 (4)
O4W—Ca1—H8W20.6H3A—N3—H3C101 (6)
C7—Ca1—H8W126.5H3B—N3—H3C106 (6)
O5—Ca2—O10164.83 (17)C13—O7—Ca1ii148.8 (4)
O5—Ca2—O1103.04 (16)C13—O8—Ca2129.6 (4)
O10—Ca2—O179.57 (15)O10—C10—O9125.4 (6)
O5—Ca2—O399.71 (17)O10—C10—C11118.0 (6)
O10—Ca2—O395.40 (16)O9—C10—C11116.5 (6)
O1—Ca2—O384.73 (16)N4—C11—C10110.4 (5)
O5—Ca2—O879.11 (16)N4—C11—C12109.4 (5)
O10—Ca2—O898.86 (16)C10—C11—C12110.3 (5)
O1—Ca2—O8177.13 (17)N4—C11—H11108.9
O3—Ca2—O893.06 (16)C10—C11—H11108.9
O5—Ca2—O3W83.61 (16)C12—C11—H11108.9
O10—Ca2—O3W81.23 (16)C11—C12—H12A109.5
O1—Ca2—O3W101.09 (17)C11—C12—H12B109.5
O3—Ca2—O3W172.56 (17)H12A—C12—H12B109.5
O8—Ca2—O3W80.97 (16)C11—C12—H12C109.5
O5—Ca2—C484.09 (17)H12A—C12—H12C109.5
O10—Ca2—C4110.90 (16)H12B—C12—H12C109.5
O1—Ca2—C474.96 (16)C11—N4—H4A114 (4)
O3—Ca2—C420.77 (16)C11—N4—H4B116 (4)
O8—Ca2—C4103.51 (17)H4A—N4—H4B107 (6)
O3W—Ca2—C4165.84 (17)C11—N4—H4C111 (4)
C1—O1—Ca2130.4 (4)H4A—N4—H4C108 (6)
C1—O2—Ca1128.8 (4)H4B—N4—H4C100 (6)
O2—C1—O1125.5 (6)C10—O9—Ca1ii129.4 (4)
O2—C1—C21119.0 (5)C10—O10—Ca2148.4 (4)
O1—C1—C21115.5 (5)O7—C13—O8127.3 (6)
N1—C21—C31109.7 (5)O7—C13—C14118.7 (6)
N1—C21—C1108.2 (5)O8—C13—C14114.0 (5)
C31—C21—C1112.2 (5)N5—C14—C15108.5 (5)
N1—C21—H21108.9N5—C14—C13109.1 (5)
C31—C21—H21108.9C15—C14—C13111.5 (5)
C1—C21—H21108.9N5—C14—H14109.2
C21—C31—H31A109.5C15—C14—H14109.2
C21—C31—H31B109.5C13—C14—H14109.2
H31A—C31—H31B109.5C14—C15—H15A109.5
C21—C31—H31C109.5C14—C15—H15B109.5
H31A—C31—H31C109.5H15A—C15—H15B109.5
H31B—C31—H31C109.5C14—C15—H15C109.5
C21—N1—H1A113 (4)H15A—C15—H15C109.5
C21—N1—H1B107 (4)H15B—C15—H15C109.5
H1A—N1—H1B103 (6)C14—N5—H5A106 (4)
C21—N1—H1C102 (4)C14—N5—H5B111 (4)
H1A—N1—H1C111 (6)H5A—N5—H5B106 (6)
H1B—N1—H1C123 (6)C14—N5—H5C108 (4)
C4—O3—Ca2117.7 (4)H5A—N5—H5C106 (6)
C4—O4—Ca1167.0 (4)H5B—N5—H5C119 (6)
O4—C4—O3125.2 (6)H1W—O1W—H2W91.4
O4—C4—C51117.9 (6)H4W—O2W—H3W110.3
O3—C4—C51116.7 (6)Ca2—O3W—H5W131.3
O4—C4—Ca283.9 (4)Ca2—O3W—H6W124.8
C51—C4—Ca2156.6 (4)H5W—O3W—H6W103.4
N2—C51—C6110.0 (5)Ca1—O4W—H7W138.5
N2—C51—C4109.1 (5)Ca1—O4W—H8W85.8
C6—C51—C4108.6 (5)H7W—O4W—H8W122.2
N2—C51—H51109.7Ca1—O5W—H9W124.3
C6—C51—H51109.7Ca1—O5W—H10W114.3
C4—C51—H51109.7H9W—O5W—H10W95.7
C51—C6—H6A109.5
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+1/2, z1/2.
(8) top
Crystal data top
C6H18MnN2O6·2(Cl)·2(H2O)Z = 2
Mr = 376.09F(000) = 390
Monoclinic, P21/cDx = 1.567 Mg m3
a = 4.7294 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 19.101 (4) ŵ = 1.19 mm1
c = 9.0705 (17) ÅT = 100 K
β = 103.395 (3)°Needle, colourless
V = 797.1 (3) Å30.40 × 0.07 × 0.07 mm
Data collection top
Bruker APEX-II CCD
diffractometer
1637 independent reflections
Radiation source: microsource1419 reflections with I > 2σ(I)
Multilayer optics monochromatorRint = 0.069
ω scansθmax = 26.5°, θmin = 2.5°
Absorption correction: multi-scan
SADABS
h = 55
Tmin = 0.565, Tmax = 0.745k = 2323
9455 measured reflectionsl = 1111
Refinement top
Refinement on F25 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.074 w = 1/[σ2(Fo2) + (0.030P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
1637 reflectionsΔρmax = 0.41 e Å3
110 parametersΔρmin = 0.28 e Å3
Crystal data top
C6H18MnN2O6·2(Cl)·2(H2O)V = 797.1 (3) Å3
Mr = 376.09Z = 2
Monoclinic, P21/cMo Kα radiation
a = 4.7294 (9) ŵ = 1.19 mm1
b = 19.101 (4) ÅT = 100 K
c = 9.0705 (17) Å0.40 × 0.07 × 0.07 mm
β = 103.395 (3)°
Data collection top
Bruker APEX-II CCD
diffractometer
1637 independent reflections
Absorption correction: multi-scan
SADABS
1419 reflections with I > 2σ(I)
Tmin = 0.565, Tmax = 0.745Rint = 0.069
9455 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0305 restraints
wR(F2) = 0.074H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.41 e Å3
1637 reflectionsΔρmin = 0.28 e Å3
110 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl11.14813 (11)0.74272 (3)0.51100 (5)0.01587 (15)
Mn20.50000.50000.50000.00991 (14)
O10.8297 (3)0.57126 (7)0.46174 (15)0.0121 (3)
O21.1996 (3)0.56861 (7)0.34688 (15)0.0129 (3)
C10.9515 (4)0.58773 (10)0.3584 (2)0.0107 (4)
C20.7897 (4)0.63498 (10)0.2301 (2)0.0130 (4)
H20.93100.66850.20220.016*
C30.6497 (5)0.59220 (12)0.0918 (2)0.0214 (5)
H3A0.50910.55960.11790.032*
H3B0.79980.56580.05710.032*
H3C0.54970.62360.01080.032*
N10.5649 (4)0.67528 (9)0.28562 (19)0.0124 (4)
H1A0.455 (4)0.7014 (10)0.206 (2)0.015*
H1B0.657 (5)0.7030 (10)0.369 (2)0.015*
H1C0.432 (4)0.6477 (10)0.319 (2)0.015*
O1W0.4853 (3)0.56036 (8)0.70187 (17)0.0162 (3)
H3D0.344 (4)0.5809 (11)0.715 (3)0.019*
H3E0.631 (4)0.5837 (11)0.728 (3)0.019*
O2W0.9933 (4)0.63929 (8)0.76154 (17)0.0200 (4)
H4B1.042 (5)0.6679 (11)0.836 (2)0.024*
H4A0.995 (5)0.6641 (11)0.685 (2)0.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0181 (3)0.0150 (3)0.0133 (3)0.0032 (2)0.0011 (2)0.00158 (19)
Mn20.0095 (3)0.0104 (2)0.0098 (2)0.00046 (16)0.00209 (18)0.00158 (16)
O10.0110 (7)0.0136 (7)0.0116 (7)0.0014 (6)0.0028 (6)0.0012 (6)
O20.0113 (8)0.0142 (7)0.0135 (7)0.0018 (6)0.0037 (6)0.0030 (6)
C10.0104 (11)0.0097 (9)0.0110 (10)0.0026 (8)0.0001 (8)0.0032 (8)
C20.0115 (11)0.0146 (10)0.0129 (10)0.0020 (8)0.0029 (8)0.0014 (8)
C30.0245 (13)0.0257 (12)0.0120 (11)0.0058 (10)0.0004 (9)0.0011 (9)
N10.0113 (9)0.0129 (9)0.0126 (9)0.0013 (7)0.0020 (7)0.0029 (7)
O1W0.0135 (8)0.0176 (8)0.0176 (8)0.0001 (6)0.0040 (7)0.0051 (6)
O2W0.0237 (9)0.0215 (8)0.0143 (8)0.0036 (7)0.0033 (7)0.0023 (6)
Geometric parameters (Å, º) top
Mn2—O1i2.1577 (14)C2—H21.0000
Mn2—O12.1577 (14)C3—H3A0.9800
Mn2—O1Wi2.1785 (15)C3—H3B0.9800
Mn2—O1W2.1785 (15)C3—H3C0.9800
Mn2—O2ii2.1795 (14)N1—H1A0.930 (15)
Mn2—O2iii2.1795 (14)N1—H1B0.946 (15)
O1—C11.249 (2)N1—H1C0.922 (15)
O2—C11.256 (2)O1W—H3D0.808 (17)
O2—Mn2iv2.1795 (14)O1W—H3E0.810 (18)
C1—C21.530 (3)O2W—H4B0.856 (18)
C2—N11.492 (3)O2W—H4A0.839 (18)
C2—C31.515 (3)
O1i—Mn2—O1180.00 (5)N1—C2—C1108.53 (16)
O1i—Mn2—O1Wi88.07 (5)C3—C2—C1110.94 (16)
O1—Mn2—O1Wi91.93 (5)N1—C2—H2109.0
O1i—Mn2—O1W91.93 (5)C3—C2—H2109.0
O1—Mn2—O1W88.07 (5)C1—C2—H2109.0
O1Wi—Mn2—O1W180.0C2—C3—H3A109.5
O1i—Mn2—O2ii95.35 (5)C2—C3—H3B109.5
O1—Mn2—O2ii84.65 (5)H3A—C3—H3B109.5
O1Wi—Mn2—O2ii85.74 (5)C2—C3—H3C109.5
O1W—Mn2—O2ii94.26 (5)H3A—C3—H3C109.5
O1i—Mn2—O2iii84.65 (5)H3B—C3—H3C109.5
O1—Mn2—O2iii95.35 (5)C2—N1—H1A109.2 (14)
O1Wi—Mn2—O2iii94.26 (5)C2—N1—H1B109.0 (14)
O1W—Mn2—O2iii85.74 (5)H1A—N1—H1B113.1 (18)
O2ii—Mn2—O2iii180.0C2—N1—H1C114.1 (13)
C1—O1—Mn2139.10 (12)H1A—N1—H1C105.0 (19)
C1—O2—Mn2iv127.23 (13)H1B—N1—H1C106 (2)
O1—C1—O2126.27 (18)Mn2—O1W—H3D125.0 (17)
O1—C1—C2118.88 (18)Mn2—O1W—H3E110.0 (17)
O2—C1—C2114.84 (17)H3D—O1W—H3E112 (2)
N1—C2—C3110.42 (17)H4B—O2W—H4A103 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x1, y, z; (iii) x+2, y+1, z+1; (iv) x+1, y, z.
(9) top
Crystal data top
C6H18MnN2O6·2(Br)·2(H2O)Z = 2
Mr = 465.01F(000) = 462
Monoclinic, P21/cDx = 1.846 Mg m3
a = 4.7592 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 19.571 (2) ŵ = 5.59 mm1
c = 9.1998 (11) ÅT = 100 K
β = 102.450 (2)°Needle, colourless
V = 836.72 (18) Å30.30 × 0.07 × 0.07 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2500 independent reflections
Radiation source: microsource2207 reflections with I > 2σ(I)
Multilayer optics monochromatorRint = 0.043
ω scansθmax = 30.8°, θmin = 2.5°
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)
h = 66
Tmin = 0.507, Tmax = 0.746k = 2727
12568 measured reflectionsl = 1313
Refinement top
Refinement on F25 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.062 w = 1/[σ2(Fo2) + (0.025P)2 + 0.5P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2500 reflectionsΔρmax = 0.83 e Å3
110 parametersΔρmin = 0.43 e Å3
Crystal data top
C6H18MnN2O6·2(Br)·2(H2O)V = 836.72 (18) Å3
Mr = 465.01Z = 2
Monoclinic, P21/cMo Kα radiation
a = 4.7592 (6) ŵ = 5.59 mm1
b = 19.571 (2) ÅT = 100 K
c = 9.1998 (11) Å0.30 × 0.07 × 0.07 mm
β = 102.450 (2)°
Data collection top
Bruker APEX-II CCD
diffractometer
2500 independent reflections
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)
2207 reflections with I > 2σ(I)
Tmin = 0.507, Tmax = 0.746Rint = 0.043
12568 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0295 restraints
wR(F2) = 0.062H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.83 e Å3
2500 reflectionsΔρmin = 0.43 e Å3
110 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br11.15542 (5)0.74336 (2)0.50714 (2)0.01593 (7)
Mn10.50000.50000.50000.00944 (10)
O10.8292 (3)0.56913 (7)0.46041 (16)0.0115 (3)
O21.2030 (3)0.56632 (7)0.34946 (16)0.0126 (3)
C10.9536 (4)0.58471 (10)0.3589 (2)0.0107 (4)
C20.7976 (4)0.63027 (11)0.2311 (2)0.0133 (4)
H20.93840.66320.20380.016*
C30.6662 (5)0.58766 (12)0.0954 (2)0.0208 (5)
H3A0.53470.55380.12260.031*
H3B0.81940.56420.05900.031*
H3C0.55970.61750.01700.031*
N10.5703 (4)0.66897 (9)0.2837 (2)0.0126 (3)
H1A0.475 (5)0.6959 (11)0.212 (2)0.015*
H1B0.651 (5)0.6954 (11)0.361 (2)0.015*
H1C0.445 (5)0.6410 (11)0.312 (3)0.015*
O1W0.4823 (3)0.55852 (8)0.69944 (18)0.0166 (3)
H3D0.351 (5)0.5763 (13)0.714 (3)0.020*
H3E0.610 (5)0.5800 (13)0.718 (3)0.020*
O2W0.9919 (4)0.63300 (9)0.75833 (19)0.0207 (4)
H4A0.984 (6)0.6528 (14)0.688 (3)0.025*
H4B1.048 (6)0.6569 (14)0.820 (3)0.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.01858 (12)0.01419 (11)0.01396 (11)0.00378 (8)0.00117 (8)0.00216 (7)
Mn10.00871 (19)0.0086 (2)0.0109 (2)0.00049 (15)0.00185 (15)0.00159 (15)
O10.0104 (7)0.0106 (7)0.0134 (7)0.0006 (5)0.0022 (6)0.0013 (5)
O20.0101 (7)0.0127 (7)0.0152 (7)0.0019 (5)0.0031 (6)0.0031 (5)
C10.0114 (9)0.0078 (8)0.0120 (9)0.0005 (7)0.0005 (7)0.0018 (7)
C20.0114 (9)0.0149 (9)0.0134 (10)0.0022 (8)0.0023 (8)0.0024 (7)
C30.0239 (12)0.0231 (11)0.0134 (10)0.0054 (9)0.0007 (9)0.0019 (8)
N10.0109 (8)0.0119 (8)0.0143 (9)0.0014 (6)0.0010 (7)0.0037 (7)
O1W0.0149 (8)0.0157 (8)0.0194 (8)0.0006 (6)0.0043 (7)0.0043 (6)
O2W0.0238 (9)0.0221 (9)0.0155 (9)0.0044 (7)0.0026 (7)0.0042 (6)
Geometric parameters (Å, º) top
Mn1—O1i2.1595 (14)C2—H21.0000
Mn1—O12.1595 (14)C3—H3A0.9800
Mn1—O1Wi2.1799 (16)C3—H3B0.9800
Mn1—O1W2.1799 (16)C3—H3C0.9800
Mn1—O2ii2.1811 (14)N1—H1A0.890 (17)
Mn1—O2iii2.1811 (14)N1—H1B0.899 (17)
O1—C11.247 (2)N1—H1C0.886 (17)
O2—C11.261 (2)O1W—H3D0.752 (19)
O2—Mn1iv2.1811 (14)O1W—H3E0.73 (2)
C1—C21.534 (3)O2W—H4A0.75 (2)
C2—N11.485 (3)O2W—H4B0.74 (2)
C2—C31.519 (3)
O1i—Mn1—O1180.00 (6)N1—C2—C1108.25 (16)
O1i—Mn1—O1Wi88.50 (6)C3—C2—C1110.88 (17)
O1—Mn1—O1Wi91.50 (6)N1—C2—H2109.1
O1i—Mn1—O1W91.50 (6)C3—C2—H2109.1
O1—Mn1—O1W88.50 (6)C1—C2—H2109.1
O1Wi—Mn1—O1W180.0C2—C3—H3A109.5
O1i—Mn1—O2ii94.90 (5)C2—C3—H3B109.5
O1—Mn1—O2ii85.10 (5)H3A—C3—H3B109.5
O1Wi—Mn1—O2ii85.16 (6)C2—C3—H3C109.5
O1W—Mn1—O2ii94.84 (6)H3A—C3—H3C109.5
O1i—Mn1—O2iii85.10 (5)H3B—C3—H3C109.5
O1—Mn1—O2iii94.90 (5)C2—N1—H1A110.6 (16)
O1Wi—Mn1—O2iii94.84 (6)C2—N1—H1B109.5 (16)
O1W—Mn1—O2iii85.16 (6)H1A—N1—H1B108 (2)
O2ii—Mn1—O2iii180.0C2—N1—H1C111.1 (16)
C1—O1—Mn1139.35 (13)H1A—N1—H1C108 (2)
C1—O2—Mn1iv128.09 (13)H1B—N1—H1C109 (2)
O1—C1—O2126.02 (19)Mn1—O1W—H3D125 (2)
O1—C1—C2119.12 (17)Mn1—O1W—H3E109 (2)
O2—C1—C2114.86 (17)H3D—O1W—H3E112 (3)
N1—C2—C3110.36 (17)H4A—O2W—H4B106 (3)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x1, y, z; (iii) x+2, y+1, z+1; (iv) x+1, y, z.
(10) top
Crystal data top
C6H18MnN2O6·2(I)·2(H2O)F(000) = 534
Mr = 558.99Dx = 2.062 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 4.794 (3) ÅCell parameters from 265 reflections
b = 20.114 (11) Åθ = 2.4–18.2°
c = 9.482 (5) ŵ = 4.19 mm1
β = 100.047 (10)°T = 100 K
V = 900.3 (9) Å3Needle, colourless
Z = 20.23 × 0.04 × 0.02 mm
Data collection top
Bruker APEX CCD
diffractometer
3312 independent reflections
Radiation source: microsource2231 reflections with I > 2σ(I)
Multilayer optics monochromatorθmax = 26.4°, θmin = 2.4°
ω scansh = 55
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)
k = 025
Tmin = 0.327, Tmax = 0.745l = 011
3312 measured reflections
Refinement top
Refinement on F26 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.063H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.143 w = 1/[σ2(Fo2) + (0.060P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3312 reflectionsΔρmax = 1.07 e Å3
111 parametersΔρmin = 1.76 e Å3
Crystal data top
C6H18MnN2O6·2(I)·2(H2O)V = 900.3 (9) Å3
Mr = 558.99Z = 2
Monoclinic, P21/cMo Kα radiation
a = 4.794 (3) ŵ = 4.19 mm1
b = 20.114 (11) ÅT = 100 K
c = 9.482 (5) Å0.23 × 0.04 × 0.02 mm
β = 100.047 (10)°
Data collection top
Bruker APEX CCD
diffractometer
3312 measured reflections
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)
3312 independent reflections
Tmin = 0.327, Tmax = 0.7452231 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0636 restraints
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 1.07 e Å3
3312 reflectionsΔρmin = 1.76 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. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I11.16518 (16)0.74663 (3)0.50202 (7)0.0201 (2)
Mn10.50000.50000.50000.0156 (5)
O10.8296 (15)0.5664 (3)0.4572 (7)0.0158 (16)
O21.2155 (15)0.5634 (3)0.3541 (7)0.0165 (16)
C10.963 (2)0.5804 (4)0.3597 (11)0.015 (2)
C20.815 (2)0.6226 (5)0.2343 (11)0.018 (2)
H20.95580.65510.20830.021*
C30.711 (3)0.5799 (5)0.1055 (11)0.023 (2)
H3A0.56040.55040.12640.034*
H3B0.86770.55320.08250.034*
H3C0.63580.60830.02360.034*
N10.584 (2)0.6600 (4)0.2804 (10)0.0172 (19)
H1A0.48 (2)0.684 (4)0.207 (8)0.021*
H1B0.65 (2)0.689 (4)0.355 (8)0.021*
H1C0.439 (17)0.631 (4)0.290 (11)0.021*
O30.4664 (18)0.5568 (4)0.6922 (9)0.024 (2)
H3D0.333 (19)0.581 (5)0.696 (13)0.028*
H3E0.57 (2)0.588 (5)0.700 (12)0.028*
O40.9751 (19)0.6267 (4)0.7476 (8)0.025 (2)
H4B0.96 (3)0.651 (5)0.814 (6)0.030*
H4A0.96 (3)0.651 (5)0.678 (6)0.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0220 (4)0.0186 (4)0.0193 (4)0.0021 (3)0.0023 (3)0.0029 (3)
Mn10.0135 (12)0.0159 (11)0.0177 (11)0.0003 (10)0.0034 (10)0.0022 (9)
O10.018 (4)0.015 (3)0.015 (4)0.001 (3)0.002 (3)0.003 (3)
O20.014 (4)0.016 (4)0.022 (4)0.001 (3)0.010 (3)0.003 (3)
C10.016 (6)0.009 (5)0.022 (6)0.001 (5)0.004 (5)0.000 (4)
C20.012 (6)0.016 (5)0.027 (6)0.002 (4)0.006 (5)0.001 (4)
C30.026 (7)0.026 (6)0.016 (5)0.004 (5)0.001 (5)0.001 (4)
N10.013 (5)0.014 (4)0.023 (5)0.001 (4)0.002 (5)0.001 (4)
O30.023 (5)0.012 (4)0.037 (5)0.001 (3)0.008 (4)0.003 (3)
O40.033 (5)0.028 (5)0.015 (4)0.007 (4)0.007 (4)0.002 (3)
Geometric parameters (Å, º) top
Mn1—O1i2.161 (7)C2—H21.0000
Mn1—O12.161 (7)C3—H3A0.9800
Mn1—O2ii2.177 (7)C3—H3B0.9800
Mn1—O2iii2.177 (7)C3—H3C0.9800
Mn1—O3i2.180 (8)N1—H1A0.93 (5)
Mn1—O32.180 (8)N1—H1B0.93 (5)
O1—C11.243 (12)N1—H1C0.93 (5)
O2—C11.270 (12)O3—H3D0.81 (7)
O2—Mn1iv2.177 (7)O3—H3E0.80 (7)
C1—C21.530 (13)O4—H4B0.81 (5)
C2—N11.467 (13)O4—H4A0.81 (5)
C2—C31.507 (13)
O1i—Mn1—O1180.0 (3)N1—C2—C1108.9 (8)
O1i—Mn1—O2ii85.2 (3)C3—C2—C1110.9 (8)
O1—Mn1—O2ii94.8 (3)N1—C2—H2108.4
O1i—Mn1—O2iii94.8 (3)C3—C2—H2108.4
O1—Mn1—O2iii85.2 (3)C1—C2—H2108.4
O2ii—Mn1—O2iii180.0C2—C3—H3A109.5
O1i—Mn1—O3i89.8 (3)C2—C3—H3B109.5
O1—Mn1—O3i90.2 (3)H3A—C3—H3B109.5
O2ii—Mn1—O3i95.5 (3)C2—C3—H3C109.5
O2iii—Mn1—O3i84.5 (3)H3A—C3—H3C109.5
O1i—Mn1—O390.2 (3)H3B—C3—H3C109.5
O1—Mn1—O389.8 (3)C2—N1—H1A113 (7)
O2ii—Mn1—O384.5 (3)C2—N1—H1B112 (7)
O2iii—Mn1—O395.5 (3)H1A—N1—H1B108 (9)
O3i—Mn1—O3180.0C2—N1—H1C109 (7)
C1—O1—Mn1140.0 (6)H1A—N1—H1C94 (9)
C1—O2—Mn1iv128.9 (6)H1B—N1—H1C119 (9)
O1—C1—O2126.0 (9)Mn1—O3—H3D121 (9)
O1—C1—C2118.5 (9)Mn1—O3—H3E110 (9)
O2—C1—C2115.6 (9)H3D—O3—H3E92 (10)
N1—C2—C3111.8 (9)H4B—O4—H4A106 (9)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z+1; (iii) x1, y, z; (iv) x+1, y, z.

Experimental details

(8)(9)(10)
Crystal data
Chemical formulaC6H18MnN2O6·2(Cl)·2(H2O)C6H18MnN2O6·2(Br)·2(H2O)C6H18MnN2O6·2(I)·2(H2O)
Mr376.09465.01558.99
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)100100100
a, b, c (Å)4.7294 (9), 19.101 (4), 9.0705 (17)4.7592 (6), 19.571 (2), 9.1998 (11)4.794 (3), 20.114 (11), 9.482 (5)
β (°) 103.395 (3) 102.450 (2) 100.047 (10)
V3)797.1 (3)836.72 (18)900.3 (9)
Z222
Radiation typeMo KαMo KαMo Kα
µ (mm1)1.195.594.19
Crystal size (mm)0.40 × 0.07 × 0.070.30 × 0.07 × 0.070.23 × 0.04 × 0.02
Data collection
DiffractometerBruker APEX-II CCD
diffractometer
Bruker APEX-II CCD
diffractometer
Bruker APEX CCD
diffractometer
Absorption correctionMulti-scan
SADABS
Multi-scan
SADABS (Sheldrick, 1996)
Multi-scan
SADABS (Sheldrick, 1996)
Tmin, Tmax0.565, 0.7450.507, 0.7460.327, 0.745
No. of measured, independent and
observed [I > 2σ(I)] reflections
9455, 1637, 1419 12568, 2500, 2207 3312, 3312, 2231
Rint0.0690.043?
(sin θ/λ)max1)0.6280.7200.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.074, 1.09 0.029, 0.062, 1.04 0.063, 0.143, 1.03
No. of reflections163725003312
No. of parameters110110111
No. of restraints556
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 refinement
Δρmax, Δρmin (e Å3)0.41, 0.280.83, 0.431.07, 1.76

Computer programs: SHELXL2013 (Sheldrick, 2013).

 

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