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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
| Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520614021398/gp5078sup1.cif Contains datablocks 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, global |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520614021398/gp50781sup2.hkl Contains datablock 1 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520614021398/gp50782sup3.hkl Contains datablock 2 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520614021398/gp50783sup4.hkl Contains datablock 3 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520614021398/gp50784sup5.hkl Contains datablock 4 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520614021398/gp50785sup6.hkl Contains datablock 5 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520614021398/gp50786sup7.hkl Contains datablock 6 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520614021398/gp50787sup8.hkl Contains datablock 7 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520614021398/gp50788sup9.hkl Contains datablock 8 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520614021398/gp50789sup10.hkl Contains datablock 9 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520614021398/gp507810sup11.hkl Contains datablock 10 |
| Portable Document Format (PDF) file https://doi.org/10.1107/S2052520614021398/gp5078sup12.pdf Refinement details, and extra figures and tables |
CCDC references: 1018134; 1018135; 1018136; 1018137; 1018138; 1018139; 1018140
Crystal data, data collection and structure refinement details are summarized
in Table 1.
S2. Results and discussion
top
For all compounds, program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013).
Crystal data top
C9H23CaN3O7·2(Br) | Z = 2 |
Mr = 485.20 | F(000) = 488 |
Monoclinic, P21 | Dx = 1.771 Mg m−3 |
a = 4.8971 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 15.812 (3) Å | µ = 4.77 mm−1 |
c = 11.773 (2) Å | T = 100 K |
β = 93.746 (3)° | Needle, colourless |
V = 909.7 (3) Å3 | 0.30 × 0.06 × 0.03 mm |
Data collection top
Bruker APEX CCD diffractometer | 3731 independent reflections |
Radiation source: microsource | 3445 reflections with I > 2σ(I) |
Multilayer optics monochromator | Rint = 0.074 |
ω scans | θmax = 26.4°, θmin = 1.7° |
Absorption correction: multi-scan SADABS | h = −6→6 |
Tmin = 0.455, Tmax = 0.745 | k = −19→19 |
10950 measured reflections | l = −14→14 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 1.02 | Δρmax = 0.67 e Å−3 |
3731 reflections | Δρmin = −0.67 e Å−3 |
235 parameters | Absolute structure: Flack x determined using 1513 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61). |
38 restraints | Absolute structure parameter: −0.007 (13) |
Crystal data top
C9H23CaN3O7·2(Br) | V = 909.7 (3) Å3 |
Mr = 485.20 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 4.8971 (9) Å | µ = 4.77 mm−1 |
b = 15.812 (3) Å | T = 100 K |
c = 11.773 (2) Å | 0.30 × 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 = 0.745 | Rint = 0.074 |
10950 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.099 | Δρmax = 0.67 e Å−3 |
S = 1.02 | Δρmin = −0.67 e Å−3 |
3731 reflections | Absolute structure: Flack x determined using 1513 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61). |
235 parameters | Absolute 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 | x | y | z | Uiso*/Ueq | |
Ca1 | 0.9046 (3) | 0.75000 (11) | 0.06889 (14) | 0.0095 (3) | |
Br1 | 0.62601 (18) | 0.64760 (5) | 0.46238 (6) | 0.0198 (2) | |
Br2 | 0.80165 (16) | 0.36363 (4) | 0.32036 (6) | 0.0151 (2) | |
O1 | 0.2738 (11) | 0.6854 (3) | 0.1640 (5) | 0.0134 (12) | |
O2 | 0.6857 (11) | 0.6305 (3) | 0.1400 (5) | 0.0142 (13) | |
C1 | 0.4435 (16) | 0.6270 (5) | 0.1705 (6) | 0.0115 (17) | |
C2 | 0.3493 (15) | 0.5403 (5) | 0.2125 (7) | 0.0106 (16) | |
H2A | 0.5010 | 0.5137 | 0.2611 | 0.013* | |
C3 | 0.274 (2) | 0.4832 (6) | 0.1114 (8) | 0.023 (2) | |
H3A | 0.2091 | 0.4287 | 0.1386 | 0.034* | |
H3B | 0.4361 | 0.4741 | 0.0680 | 0.034* | |
H3C | 0.1299 | 0.5100 | 0.0623 | 0.034* | |
N1 | 0.1083 (15) | 0.5528 (5) | 0.2812 (6) | 0.0133 (14) | |
H1N | 0.136 (19) | 0.585 (5) | 0.344 (5) | 0.016* | |
H2N | −0.028 (13) | 0.577 (5) | 0.239 (6) | 0.016* | |
H3N | 0.066 (19) | 0.502 (3) | 0.306 (7) | 0.016* | |
O3 | 0.5333 (10) | 0.7620 (4) | −0.0654 (4) | 0.0115 (12) | |
O4 | 0.1190 (11) | 0.7043 (3) | −0.0977 (5) | 0.0126 (12) | |
C4 | 0.3632 (17) | 0.7164 (5) | −0.1203 (6) | 0.0129 (17) | |
C5 | 0.4584 (17) | 0.6686 (5) | −0.2224 (6) | 0.0129 (17) | |
H5A | 0.3022 | 0.6632 | −0.2810 | 0.015* | |
C6 | 0.5589 (19) | 0.5813 (5) | −0.1876 (7) | 0.0180 (18) | |
H6A | 0.6286 | 0.5525 | −0.2535 | 0.027* | |
H6B | 0.4073 | 0.5486 | −0.1595 | 0.027* | |
H6C | 0.7057 | 0.5862 | −0.1273 | 0.027* | |
N2 | 0.6828 (15) | 0.7171 (5) | −0.2713 (6) | 0.0130 (14) | |
H4N | 0.844 (11) | 0.714 (6) | −0.232 (7) | 0.016* | |
H5N | 0.714 (18) | 0.693 (5) | −0.338 (5) | 0.016* | |
H6N | 0.643 (18) | 0.771 (3) | −0.289 (7) | 0.016* | |
O5 | 0.7518 (12) | 0.8303 (4) | 0.2094 (5) | 0.0161 (12) | |
O6 | 0.3726 (11) | 0.8859 (3) | 0.2718 (4) | 0.0135 (12) | |
C7 | 0.6146 (15) | 0.8613 (5) | 0.2845 (6) | 0.0128 (15) | |
C8 | 0.7586 (15) | 0.8745 (5) | 0.4012 (6) | 0.0120 (16) | |
H8A | 0.6298 | 0.8603 | 0.4609 | 0.014* | |
C9 | 0.8480 (19) | 0.9678 (6) | 0.4150 (7) | 0.0189 (19) | |
H9A | 0.9778 | 0.9734 | 0.4815 | 0.028* | |
H9B | 0.6872 | 1.0032 | 0.4254 | 0.028* | |
H9C | 0.9356 | 0.9862 | 0.3466 | 0.028* | |
N3 | 1.0034 (14) | 0.8185 (4) | 0.4153 (6) | 0.0137 (14) | |
H7N | 1.079 (18) | 0.826 (6) | 0.486 (4) | 0.016* | |
H8N | 0.957 (18) | 0.764 (3) | 0.406 (7) | 0.016* | |
H9N | 1.118 (15) | 0.834 (5) | 0.362 (6) | 0.016* | |
O1W | 1.1758 (12) | 0.8728 (4) | 0.0495 (5) | 0.0159 (13) | |
H1W | 1.241 (19) | 0.880 (6) | 0.109 (6) | 0.019* | |
H2W | 1.292 (17) | 0.856 (7) | 0.018 (7) | 0.019* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ca1 | 0.0084 (7) | 0.0084 (7) | 0.0115 (6) | −0.0002 (6) | −0.0014 (5) | 0.0000 (6) |
Br1 | 0.0271 (5) | 0.0175 (4) | 0.0147 (4) | −0.0089 (4) | 0.0005 (3) | −0.0022 (3) |
Br2 | 0.0176 (4) | 0.0105 (4) | 0.0165 (4) | −0.0022 (3) | −0.0040 (3) | 0.0009 (3) |
O1 | 0.010 (3) | 0.007 (3) | 0.023 (3) | 0.001 (2) | −0.005 (2) | 0.004 (2) |
O2 | 0.008 (3) | 0.015 (3) | 0.019 (3) | −0.002 (2) | −0.001 (2) | 0.003 (2) |
C1 | 0.012 (4) | 0.012 (4) | 0.009 (4) | −0.002 (3) | −0.003 (3) | 0.002 (3) |
C2 | 0.007 (4) | 0.008 (4) | 0.017 (4) | 0.000 (3) | −0.002 (3) | 0.001 (3) |
C3 | 0.027 (5) | 0.017 (5) | 0.026 (5) | −0.007 (4) | 0.005 (4) | −0.005 (4) |
N1 | 0.012 (4) | 0.010 (3) | 0.018 (4) | 0.001 (3) | 0.000 (3) | 0.003 (3) |
O3 | 0.011 (3) | 0.011 (3) | 0.012 (2) | 0.002 (2) | −0.004 (2) | −0.002 (2) |
O4 | 0.007 (3) | 0.015 (3) | 0.015 (3) | −0.002 (2) | −0.001 (2) | −0.003 (2) |
C4 | 0.016 (4) | 0.013 (4) | 0.008 (3) | 0.005 (3) | −0.003 (3) | 0.003 (3) |
C5 | 0.015 (4) | 0.008 (4) | 0.015 (4) | −0.002 (3) | −0.001 (3) | 0.000 (3) |
C6 | 0.023 (5) | 0.010 (4) | 0.021 (4) | −0.002 (4) | −0.001 (4) | 0.001 (3) |
N2 | 0.012 (4) | 0.016 (4) | 0.011 (3) | −0.001 (3) | −0.001 (3) | −0.003 (3) |
O5 | 0.015 (3) | 0.019 (3) | 0.015 (3) | −0.001 (2) | 0.002 (2) | −0.008 (2) |
O6 | 0.011 (3) | 0.013 (3) | 0.016 (3) | 0.000 (2) | −0.001 (2) | −0.001 (2) |
C7 | 0.013 (4) | 0.006 (3) | 0.020 (4) | −0.003 (4) | 0.004 (3) | 0.000 (3) |
C8 | 0.006 (3) | 0.014 (4) | 0.016 (4) | 0.003 (3) | 0.001 (3) | −0.003 (3) |
C9 | 0.023 (5) | 0.016 (4) | 0.018 (4) | 0.000 (4) | −0.006 (4) | −0.008 (4) |
N3 | 0.008 (4) | 0.012 (4) | 0.021 (4) | −0.001 (3) | 0.002 (3) | 0.001 (3) |
O1W | 0.017 (3) | 0.014 (3) | 0.016 (3) | −0.002 (3) | −0.002 (2) | −0.003 (3) |
Geometric parameters (Å, º) top
Ca1—O5 | 2.251 (6) | C4—C5 | 1.519 (11) |
Ca1—O1i | 2.302 (5) | C5—N2 | 1.487 (10) |
Ca1—O3 | 2.338 (5) | C5—C6 | 1.514 (11) |
Ca1—O2 | 2.353 (6) | C5—H5A | 1.0000 |
Ca1—O1W | 2.372 (6) | C6—H6A | 0.9800 |
Ca1—O4i | 2.396 (6) | C6—H6B | 0.9800 |
Ca1—H1W | 2.66 (10) | C6—H6C | 0.9800 |
Ca1—H2W | 2.63 (10) | N2—H4N | 0.89 (3) |
O1—C1 | 1.242 (9) | N2—H5N | 0.90 (3) |
O1—Ca1ii | 2.302 (5) | N2—H6N | 0.89 (3) |
O2—C1 | 1.262 (9) | O5—C7 | 1.246 (9) |
C1—C2 | 1.538 (11) | O6—C7 | 1.247 (9) |
C2—N1 | 1.487 (10) | C7—C8 | 1.518 (10) |
C2—C3 | 1.520 (12) | C8—N3 | 1.491 (10) |
C2—H2A | 1.0000 | C8—C9 | 1.545 (12) |
C3—H3A | 0.9800 | C8—H8A | 1.0000 |
C3—H3B | 0.9800 | C9—H9A | 0.9800 |
C3—H3C | 0.9800 | C9—H9B | 0.9800 |
N1—H1N | 0.90 (3) | C9—H9C | 0.9800 |
N1—H2N | 0.89 (3) | N3—H7N | 0.90 (3) |
N1—H3N | 0.89 (3) | N3—H8N | 0.90 (3) |
O3—C4 | 1.249 (9) | N3—H9N | 0.90 (3) |
O4—C4 | 1.257 (10) | O1W—H1W | 0.76 (6) |
O4—Ca1ii | 2.396 (6) | O1W—H2W | 0.75 (6) |
| | | |
O5—Ca1—O1i | 100.4 (2) | H2N—N1—H3N | 113 (8) |
O5—Ca1—O3 | 99.8 (2) | C4—O3—Ca1 | 140.0 (5) |
O1i—Ca1—O3 | 156.4 (2) | C4—O4—Ca1ii | 127.0 (5) |
O5—Ca1—O2 | 90.6 (2) | O3—C4—O4 | 126.1 (7) |
O1i—Ca1—O2 | 80.36 (19) | O3—C4—C5 | 117.9 (7) |
O3—Ca1—O2 | 87.3 (2) | O4—C4—C5 | 115.9 (7) |
O5—Ca1—O1W | 79.9 (2) | N2—C5—C6 | 109.9 (7) |
O1i—Ca1—O1W | 89.0 (2) | N2—C5—C4 | 108.8 (6) |
O3—Ca1—O1W | 106.5 (2) | C6—C5—C4 | 110.6 (6) |
O2—Ca1—O1W | 164.3 (2) | N2—C5—H5A | 109.2 |
O5—Ca1—O4i | 162.9 (2) | C6—C5—H5A | 109.2 |
O1i—Ca1—O4i | 83.8 (2) | C4—C5—H5A | 109.2 |
O3—Ca1—O4i | 80.45 (19) | C5—C6—H6A | 109.5 |
O2—Ca1—O4i | 106.5 (2) | C5—C6—H6B | 109.5 |
O1W—Ca1—O4i | 83.7 (2) | H6A—C6—H6B | 109.5 |
O5—Ca1—H1W | 70.5 (19) | C5—C6—H6C | 109.5 |
O1i—Ca1—H1W | 78 (2) | H6A—C6—H6C | 109.5 |
O3—Ca1—H1W | 120.1 (18) | H6B—C6—H6C | 109.5 |
O2—Ca1—H1W | 148.3 (16) | C5—N2—H4N | 115 (6) |
O1W—Ca1—H1W | 16.0 (15) | C5—N2—H5N | 108 (6) |
O4i—Ca1—H1W | 94.5 (18) | H4N—N2—H5N | 104 (8) |
O5—Ca1—H2W | 95.1 (17) | C5—N2—H6N | 115 (6) |
O1i—Ca1—H2W | 81 (2) | H4N—N2—H6N | 111 (8) |
O3—Ca1—H2W | 110 (2) | H5N—N2—H6N | 104 (8) |
O2—Ca1—H2W | 161 (2) | C7—O5—Ca1 | 164.6 (6) |
O1W—Ca1—H2W | 16.3 (17) | O5—C7—O6 | 126.2 (7) |
O4i—Ca1—H2W | 69.0 (17) | O5—C7—C8 | 117.2 (7) |
H1W—Ca1—H2W | 26 (3) | O6—C7—C8 | 116.6 (7) |
C1—O1—Ca1ii | 149.5 (5) | N3—C8—C7 | 110.0 (6) |
C1—O2—Ca1 | 126.5 (5) | N3—C8—C9 | 109.6 (6) |
O1—C1—O2 | 125.9 (7) | C7—C8—C9 | 109.8 (7) |
O1—C1—C2 | 118.0 (7) | N3—C8—H8A | 109.2 |
O2—C1—C2 | 116.0 (7) | C7—C8—H8A | 109.2 |
N1—C2—C3 | 110.2 (7) | C9—C8—H8A | 109.2 |
N1—C2—C1 | 108.8 (6) | C8—C9—H9A | 109.5 |
C3—C2—C1 | 109.9 (6) | C8—C9—H9B | 109.5 |
N1—C2—H2A | 109.3 | H9A—C9—H9B | 109.5 |
C3—C2—H2A | 109.3 | C8—C9—H9C | 109.5 |
C1—C2—H2A | 109.3 | H9A—C9—H9C | 109.5 |
C2—C3—H3A | 109.5 | H9B—C9—H9C | 109.5 |
C2—C3—H3B | 109.5 | C8—N3—H7N | 108 (6) |
H3A—C3—H3B | 109.5 | C8—N3—H8N | 111 (6) |
C2—C3—H3C | 109.5 | H7N—N3—H8N | 109 (8) |
H3A—C3—H3C | 109.5 | C8—N3—H9N | 107 (6) |
H3B—C3—H3C | 109.5 | H7N—N3—H9N | 112 (8) |
C2—N1—H1N | 116 (6) | H8N—N3—H9N | 110 (8) |
C2—N1—H2N | 110 (6) | Ca1—O1W—H1W | 104 (8) |
H1N—N1—H2N | 106 (8) | Ca1—O1W—H2W | 102 (8) |
C2—N1—H3N | 106 (6) | H1W—O1W—H2W | 103 (10) |
H1N—N1—H3N | 106 (8) | | |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
Crystal data top
C9H23CaN3O7·2(I) | Z = 2 |
Mr = 579.18 | F(000) = 560 |
Monoclinic, P21 | Dx = 1.981 Mg m−3 |
a = 4.9164 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 16.416 (3) Å | µ = 3.53 mm−1 |
c = 12.039 (2) Å | T = 100 K |
β = 92.435 (3)° | Needle, colourless |
V = 970.8 (3) Å3 | 0.20 × 0.04 × 0.03 mm |
Data collection top
Bruker APEX CCD diffractometer | 3955 independent reflections |
Radiation source: microsource | 3580 reflections with I > 2σ(I) |
Multilayer optics monochromator | Rint = 0.063 |
ω scans | θmax = 26.4°, θmin = 2.5° |
Absorption correction: multi-scan SADABS | h = −6→6 |
Tmin = 0.554, Tmax = 0.745 | k = −20→20 |
11583 measured reflections | l = −15→15 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 1.03 | Δρmax = 0.71 e Å−3 |
3955 reflections | Δρmin = −0.61 e Å−3 |
235 parameters | Absolute structure: Flack x determined using 1553 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61). |
50 restraints | Absolute structure parameter: −0.04 (3) |
Crystal data top
C9H23CaN3O7·2(I) | V = 970.8 (3) Å3 |
Mr = 579.18 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 4.9164 (8) Å | µ = 3.53 mm−1 |
b = 16.416 (3) Å | T = 100 K |
c = 12.039 (2) Å | 0.20 × 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 = 0.745 | Rint = 0.063 |
11583 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.065 | Δρmax = 0.71 e Å−3 |
S = 1.03 | Δρmin = −0.61 e Å−3 |
3955 reflections | Absolute structure: Flack x determined using 1553 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61). |
235 parameters | Absolute 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 | x | y | z | Uiso*/Ueq | |
I1 | 0.77508 (13) | 0.36750 (3) | 0.32244 (5) | 0.01822 (16) | |
I2 | 0.62059 (14) | 0.64888 (4) | 0.45882 (5) | 0.02179 (17) | |
Ca1 | 0.9183 (4) | 0.75002 (12) | 0.06479 (17) | 0.0120 (4) | |
O1W | 1.1891 (13) | 0.8687 (5) | 0.0436 (5) | 0.0167 (14) | |
H1W | 1.303 (17) | 0.849 (6) | 0.001 (7) | 0.020* | |
H2W | 1.271 (18) | 0.880 (6) | 0.104 (6) | 0.020* | |
O1 | 0.2805 (13) | 0.6869 (4) | 0.1558 (5) | 0.0165 (15) | |
O2 | 0.6910 (13) | 0.6334 (4) | 0.1296 (5) | 0.0182 (16) | |
C1 | 0.4470 (19) | 0.6301 (5) | 0.1596 (7) | 0.013 (2) | |
C2 | 0.348 (2) | 0.5470 (6) | 0.1982 (8) | 0.016 (2) | |
H2 | 0.4967 | 0.5207 | 0.2449 | 0.019* | |
C3 | 0.279 (3) | 0.4925 (6) | 0.0994 (9) | 0.028 (3) | |
H3A | 0.2159 | 0.4395 | 0.1258 | 0.041* | |
H3B | 0.4413 | 0.4848 | 0.0561 | 0.041* | |
H3C | 0.1349 | 0.5179 | 0.0525 | 0.041* | |
N1 | 0.1079 (17) | 0.5577 (5) | 0.2663 (7) | 0.0126 (18) | |
H1N | −0.034 (13) | 0.581 (5) | 0.221 (6) | 0.015* | |
H2N | 0.174 (17) | 0.584 (5) | 0.332 (5) | 0.015* | |
H3N | 0.058 (18) | 0.505 (3) | 0.291 (7) | 0.015* | |
O3 | 0.5575 (15) | 0.7602 (5) | −0.0660 (6) | 0.0160 (14) | |
O4 | 0.1440 (14) | 0.7032 (4) | −0.0950 (6) | 0.0174 (16) | |
C4 | 0.389 (2) | 0.7165 (6) | −0.1182 (8) | 0.016 (2) | |
C5 | 0.4883 (19) | 0.6697 (5) | −0.2183 (8) | 0.014 (2) | |
H5 | 0.3378 | 0.6665 | −0.2766 | 0.017* | |
C6 | 0.578 (2) | 0.5832 (6) | −0.1856 (9) | 0.021 (2) | |
H6A | 0.6433 | 0.5549 | −0.2510 | 0.032* | |
H6B | 0.4238 | 0.5534 | −0.1566 | 0.032* | |
H6C | 0.7256 | 0.5860 | −0.1282 | 0.032* | |
N2 | 0.7248 (18) | 0.7148 (5) | −0.2641 (7) | 0.0144 (18) | |
H4N | 0.648 (18) | 0.766 (3) | −0.283 (8) | 0.017* | |
H5N | 0.744 (19) | 0.703 (6) | −0.341 (3) | 0.017* | |
H6N | 0.882 (13) | 0.717 (6) | −0.215 (7) | 0.017* | |
O5 | 0.7670 (14) | 0.8290 (4) | 0.2022 (6) | 0.0193 (16) | |
O6 | 0.3879 (13) | 0.8871 (4) | 0.2589 (5) | 0.0196 (16) | |
N3 | 1.0119 (18) | 0.8253 (5) | 0.4015 (7) | 0.018 (2) | |
H7N | 0.950 (19) | 0.770 (3) | 0.399 (8) | 0.022* | |
H8N | 1.129 (17) | 0.841 (5) | 0.344 (6) | 0.022* | |
H9N | 1.092 (18) | 0.838 (6) | 0.473 (4) | 0.022* | |
C7 | 0.6250 (19) | 0.8623 (6) | 0.2739 (7) | 0.016 (2) | |
C8 | 0.7610 (18) | 0.8762 (6) | 0.3884 (7) | 0.0135 (19) | |
H8 | 0.6318 | 0.8605 | 0.4467 | 0.016* | |
C9 | 0.837 (2) | 0.9659 (6) | 0.4028 (9) | 0.027 (3) | |
H9A | 0.9469 | 0.9729 | 0.4721 | 0.041* | |
H9B | 0.6714 | 0.9987 | 0.4057 | 0.041* | |
H9C | 0.9429 | 0.9835 | 0.3399 | 0.041* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0214 (4) | 0.0132 (3) | 0.0198 (3) | −0.0021 (3) | −0.0029 (3) | 0.0015 (3) |
I2 | 0.0281 (4) | 0.0218 (3) | 0.0155 (3) | −0.0075 (3) | 0.0017 (3) | −0.0027 (3) |
Ca1 | 0.0118 (9) | 0.0129 (9) | 0.0113 (9) | 0.0008 (8) | −0.0005 (7) | −0.0001 (7) |
O1W | 0.018 (4) | 0.019 (3) | 0.013 (3) | −0.002 (4) | 0.002 (3) | −0.004 (4) |
O1 | 0.016 (4) | 0.013 (3) | 0.021 (4) | 0.006 (3) | 0.001 (3) | 0.002 (3) |
O2 | 0.013 (4) | 0.019 (4) | 0.022 (4) | 0.001 (3) | −0.003 (3) | 0.001 (3) |
C1 | 0.016 (5) | 0.014 (5) | 0.010 (5) | 0.001 (4) | −0.002 (4) | 0.001 (4) |
C2 | 0.015 (5) | 0.014 (5) | 0.018 (5) | 0.000 (4) | 0.002 (4) | 0.002 (4) |
C3 | 0.035 (7) | 0.023 (7) | 0.025 (6) | −0.007 (5) | 0.002 (5) | 0.001 (5) |
N1 | 0.006 (4) | 0.016 (4) | 0.016 (5) | −0.001 (3) | 0.003 (3) | 0.002 (3) |
O3 | 0.019 (4) | 0.018 (3) | 0.011 (3) | −0.004 (3) | −0.003 (3) | −0.001 (3) |
O4 | 0.014 (4) | 0.021 (4) | 0.017 (4) | 0.001 (3) | 0.002 (3) | −0.005 (3) |
C4 | 0.017 (6) | 0.016 (5) | 0.014 (5) | 0.004 (4) | 0.001 (4) | 0.010 (4) |
C5 | 0.013 (5) | 0.016 (5) | 0.015 (5) | −0.002 (4) | 0.007 (4) | 0.001 (4) |
C6 | 0.026 (6) | 0.011 (5) | 0.026 (6) | −0.001 (5) | 0.002 (5) | 0.000 (4) |
N2 | 0.017 (5) | 0.018 (4) | 0.009 (4) | −0.007 (4) | 0.002 (4) | −0.001 (4) |
O5 | 0.014 (4) | 0.023 (4) | 0.021 (4) | 0.000 (3) | 0.001 (3) | −0.007 (3) |
O6 | 0.015 (4) | 0.020 (4) | 0.024 (4) | 0.003 (3) | 0.001 (3) | −0.001 (3) |
N3 | 0.018 (5) | 0.015 (5) | 0.022 (5) | 0.004 (4) | −0.001 (4) | 0.000 (4) |
C7 | 0.024 (6) | 0.011 (4) | 0.013 (5) | −0.006 (5) | 0.000 (4) | −0.002 (4) |
C8 | 0.013 (3) | 0.017 (4) | 0.011 (3) | 0.003 (3) | 0.005 (3) | −0.002 (3) |
C9 | 0.034 (6) | 0.019 (5) | 0.027 (5) | −0.001 (4) | −0.008 (5) | −0.016 (4) |
Geometric parameters (Å, º) top
Ca1—O5 | 2.253 (7) | O3—C4 | 1.245 (12) |
Ca1—O1i | 2.298 (7) | O4—C4 | 1.267 (11) |
Ca1—O3 | 2.327 (7) | O4—Ca1ii | 2.388 (7) |
Ca1—O2 | 2.365 (7) | C4—C5 | 1.527 (12) |
Ca1—O1W | 2.380 (8) | C5—N2 | 1.503 (12) |
Ca1—O4i | 2.388 (7) | C5—C6 | 1.534 (13) |
O1—C1 | 1.241 (10) | O5—C7 | 1.258 (11) |
O1—Ca1ii | 2.298 (7) | O6—C7 | 1.241 (11) |
O2—C1 | 1.269 (10) | N3—C8 | 1.492 (12) |
C1—C2 | 1.528 (12) | C7—C8 | 1.523 (12) |
C2—N1 | 1.477 (12) | C8—C9 | 1.527 (14) |
C2—C3 | 1.515 (14) | | |
| | | |
O5—Ca1—O1i | 100.5 (3) | O2—C1—C2 | 116.2 (8) |
O5—Ca1—O3 | 100.9 (3) | N1—C2—C3 | 110.4 (8) |
O1i—Ca1—O3 | 155.2 (3) | N1—C2—C1 | 109.6 (8) |
O5—Ca1—O2 | 92.8 (2) | C3—C2—C1 | 110.6 (8) |
O1i—Ca1—O2 | 81.1 (2) | C4—O3—Ca1 | 140.5 (7) |
O3—Ca1—O2 | 85.6 (2) | C4—O4—Ca1ii | 126.9 (6) |
O5—Ca1—O1W | 79.1 (2) | O3—C4—O4 | 127.3 (9) |
O1i—Ca1—O1W | 89.7 (2) | O3—C4—C5 | 117.3 (9) |
O3—Ca1—O1W | 106.4 (3) | O4—C4—C5 | 115.2 (9) |
O2—Ca1—O1W | 166.5 (2) | N2—C5—C4 | 108.7 (7) |
O5—Ca1—O4i | 162.9 (3) | N2—C5—C6 | 109.4 (8) |
O1i—Ca1—O4i | 82.0 (2) | C4—C5—C6 | 111.2 (8) |
O3—Ca1—O4i | 81.1 (3) | C7—O5—Ca1 | 164.6 (6) |
O2—Ca1—O4i | 104.3 (2) | O6—C7—O5 | 126.0 (9) |
O1W—Ca1—O4i | 84.0 (2) | O6—C7—C8 | 117.1 (8) |
C1—O1—Ca1ii | 148.5 (6) | O5—C7—C8 | 116.8 (8) |
C1—O2—Ca1 | 126.5 (6) | N3—C8—C7 | 109.9 (8) |
O1—C1—O2 | 126.0 (9) | N3—C8—C9 | 109.2 (8) |
O1—C1—C2 | 117.7 (8) | C7—C8—C9 | 110.1 (8) |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
Crystal data top
C9H23MnN3O7·2(Br) | Z = 2 |
Mr = 500.06 | F(000) = 498 |
Monoclinic, P21 | Dx = 1.905 Mg m−3 |
a = 4.7809 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 15.7146 (13) Å | µ = 5.38 mm−1 |
c = 11.6246 (10) Å | T = 100 K |
β = 93.581 (1)° | Block, colourless |
V = 871.65 (13) Å3 | 0.19 × 0.15 × 0.07 mm |
Data collection top
Bruker APEX CCD diffractometer | 4600 independent reflections |
Radiation source: microsource | 4269 reflections with I > 2σ(I) |
Multilayer optics monochromator | Rint = 0.046 |
ω scans | θmax = 29.0°, θmin = 2.2° |
Absorption correction: multi-scan SADABS | h = −6→6 |
Tmin = 0.486, Tmax = 0.746 | k = −21→21 |
12613 measured reflections | l = −15→15 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 1.00 | Δρmax = 0.46 e Å−3 |
4600 reflections | Δρmin = −0.35 e Å−3 |
234 parameters | Absolute structure: Flack x determined using 1890 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61). |
12 restraints | Absolute structure parameter: −0.028 (7) |
Crystal data top
C9H23MnN3O7·2(Br) | V = 871.65 (13) Å3 |
Mr = 500.06 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 4.7809 (4) Å | µ = 5.38 mm−1 |
b = 15.7146 (13) Å | T = 100 K |
c = 11.6246 (10) Å | 0.19 × 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 = 0.746 | Rint = 0.046 |
12613 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.059 | Δρmax = 0.46 e Å−3 |
S = 1.00 | Δρmin = −0.35 e Å−3 |
4600 reflections | Absolute structure: Flack x determined using 1890 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61). |
234 parameters | Absolute 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 | x | y | z | Uiso*/Ueq | |
Mn1 | 0.90766 (15) | 0.74999 (5) | 0.06999 (6) | 0.00787 (14) | |
Br1 | 0.79653 (10) | 0.36550 (3) | 0.31414 (4) | 0.01299 (11) | |
Br2 | 0.61843 (10) | 0.64821 (3) | 0.46537 (4) | 0.01540 (12) | |
O1 | 0.2712 (7) | 0.6937 (2) | 0.1663 (3) | 0.0106 (7) | |
O2 | 0.6911 (6) | 0.6388 (2) | 0.1310 (3) | 0.0121 (7) | |
C1 | 0.4438 (9) | 0.6349 (3) | 0.1655 (4) | 0.0092 (9) | |
C2 | 0.3558 (10) | 0.5469 (3) | 0.2053 (4) | 0.0106 (9) | |
H2 | 0.5147 | 0.5206 | 0.2528 | 0.013* | |
C3 | 0.2774 (11) | 0.4897 (3) | 0.1029 (4) | 0.0175 (11) | |
H3A | 0.2214 | 0.4337 | 0.1305 | 0.026* | |
H3B | 0.4390 | 0.4834 | 0.0557 | 0.026* | |
H3C | 0.1211 | 0.5152 | 0.0563 | 0.026* | |
N1 | 0.1096 (9) | 0.5568 (3) | 0.2780 (4) | 0.0109 (8) | |
H1N | 0.054 (11) | 0.504 (2) | 0.296 (4) | 0.013* | |
H2N | −0.029 (8) | 0.588 (3) | 0.242 (4) | 0.013* | |
H3N | 0.160 (11) | 0.585 (3) | 0.345 (3) | 0.013* | |
O3 | 0.5479 (7) | 0.7651 (2) | −0.0571 (3) | 0.0093 (7) | |
O4 | 0.1248 (7) | 0.7031 (2) | −0.0831 (3) | 0.0110 (7) | |
C4 | 0.3735 (9) | 0.7172 (3) | −0.1103 (4) | 0.0085 (9) | |
C5 | 0.4672 (10) | 0.6687 (3) | −0.2145 (4) | 0.0102 (9) | |
H5 | 0.3050 | 0.6643 | −0.2729 | 0.012* | |
C6 | 0.5648 (11) | 0.5800 (3) | −0.1821 (5) | 0.0171 (11) | |
H6A | 0.6228 | 0.5503 | −0.2508 | 0.026* | |
H6B | 0.4113 | 0.5486 | −0.1495 | 0.026* | |
H6C | 0.7239 | 0.5834 | −0.1248 | 0.026* | |
N2 | 0.6946 (9) | 0.7180 (3) | −0.2655 (4) | 0.0115 (8) | |
H4N | 0.649 (11) | 0.7744 (19) | −0.277 (5) | 0.014* | |
H5N | 0.723 (11) | 0.691 (3) | −0.334 (3) | 0.014* | |
H6N | 0.855 (8) | 0.717 (3) | −0.223 (4) | 0.014* | |
O5 | 0.7764 (7) | 0.8219 (2) | 0.2086 (3) | 0.0146 (7) | |
O6 | 0.3859 (7) | 0.8844 (2) | 0.2654 (3) | 0.0129 (7) | |
C7 | 0.6313 (9) | 0.8570 (3) | 0.2812 (4) | 0.0117 (9) | |
C8 | 0.7722 (9) | 0.8727 (3) | 0.4010 (4) | 0.0105 (9) | |
H8 | 0.6375 | 0.8590 | 0.4608 | 0.013* | |
C9 | 0.8616 (11) | 0.9657 (3) | 0.4131 (5) | 0.0183 (11) | |
H9A | 0.9819 | 0.9729 | 0.4838 | 0.027* | |
H9B | 0.6950 | 1.0017 | 0.4167 | 0.027* | |
H9C | 0.9652 | 0.9822 | 0.3465 | 0.027* | |
N3 | 1.0218 (9) | 0.8160 (3) | 0.4166 (4) | 0.0123 (8) | |
H7N | 0.949 (11) | 0.763 (2) | 0.417 (5) | 0.015* | |
H8N | 1.101 (10) | 0.826 (4) | 0.490 (3) | 0.015* | |
H9N | 1.136 (10) | 0.828 (3) | 0.361 (4) | 0.015* | |
O1W | 1.1545 (7) | 0.8656 (2) | 0.0490 (3) | 0.0117 (6) | |
H1W | 1.286 (8) | 0.856 (4) | 0.010 (4) | 0.014* | |
H2W | 1.228 (10) | 0.872 (4) | 0.113 (3) | 0.014* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Mn1 | 0.0065 (3) | 0.0092 (3) | 0.0079 (3) | 0.0002 (3) | 0.0002 (2) | −0.0001 (3) |
Br1 | 0.0143 (2) | 0.0112 (2) | 0.0131 (2) | −0.0020 (2) | −0.00191 (17) | 0.00100 (19) |
Br2 | 0.0193 (3) | 0.0161 (3) | 0.0107 (2) | −0.0058 (2) | 0.00069 (18) | −0.0016 (2) |
O1 | 0.0096 (16) | 0.0095 (17) | 0.0126 (17) | 0.0012 (13) | −0.0001 (13) | 0.0012 (14) |
O2 | 0.0076 (15) | 0.0122 (18) | 0.0165 (17) | −0.0020 (14) | 0.0018 (13) | 0.0030 (15) |
C1 | 0.006 (2) | 0.015 (3) | 0.007 (2) | −0.0010 (18) | −0.0027 (16) | 0.0025 (18) |
C2 | 0.006 (2) | 0.013 (2) | 0.013 (2) | 0.0000 (18) | 0.0029 (17) | 0.0028 (19) |
C3 | 0.022 (3) | 0.013 (3) | 0.017 (3) | −0.003 (2) | 0.003 (2) | −0.004 (2) |
N1 | 0.009 (2) | 0.011 (2) | 0.013 (2) | −0.0027 (16) | 0.0011 (16) | 0.0008 (17) |
O3 | 0.0090 (16) | 0.0113 (17) | 0.0075 (16) | 0.0001 (13) | −0.0010 (12) | −0.0008 (13) |
O4 | 0.0082 (16) | 0.0160 (18) | 0.0088 (16) | −0.0020 (13) | 0.0000 (13) | −0.0030 (13) |
C4 | 0.009 (2) | 0.009 (2) | 0.008 (2) | 0.0033 (17) | −0.0011 (17) | 0.0028 (17) |
C5 | 0.009 (2) | 0.012 (2) | 0.009 (2) | −0.0021 (18) | 0.0002 (17) | −0.0042 (18) |
C6 | 0.020 (3) | 0.013 (3) | 0.018 (3) | −0.002 (2) | 0.004 (2) | −0.002 (2) |
N2 | 0.010 (2) | 0.016 (2) | 0.0084 (19) | −0.0006 (17) | 0.0011 (16) | −0.0006 (17) |
O5 | 0.0093 (16) | 0.022 (2) | 0.0131 (17) | −0.0026 (15) | 0.0044 (14) | −0.0088 (15) |
O6 | 0.0111 (16) | 0.0129 (18) | 0.0145 (17) | −0.0002 (13) | −0.0011 (13) | −0.0004 (13) |
C7 | 0.011 (2) | 0.008 (2) | 0.015 (2) | −0.0044 (19) | 0.0015 (18) | 0.001 (2) |
C8 | 0.009 (2) | 0.014 (2) | 0.008 (2) | 0.001 (2) | −0.0025 (16) | 0.000 (2) |
C9 | 0.020 (3) | 0.013 (2) | 0.021 (3) | 0.000 (2) | −0.006 (2) | −0.003 (2) |
N3 | 0.012 (2) | 0.014 (2) | 0.011 (2) | 0.0000 (17) | 0.0007 (16) | −0.0007 (17) |
O1W | 0.0111 (16) | 0.0136 (16) | 0.0104 (16) | −0.0001 (16) | −0.0005 (12) | 0.0008 (16) |
Geometric parameters (Å, º) top
Mn1—O5 | 2.097 (3) | C5—N2 | 1.488 (6) |
Mn1—O2 | 2.173 (3) | C5—C6 | 1.511 (7) |
Mn1—O1W | 2.189 (4) | C5—H5 | 1.0000 |
Mn1—O1i | 2.194 (3) | C6—H6A | 0.9800 |
Mn1—O3 | 2.209 (3) | C6—H6B | 0.9800 |
Mn1—O4i | 2.241 (3) | C6—H6C | 0.9800 |
O1—C1 | 1.239 (6) | N2—H4N | 0.92 (3) |
O1—Mn1ii | 2.194 (3) | N2—H5N | 0.92 (3) |
O2—C1 | 1.274 (5) | N2—H6N | 0.89 (3) |
C1—C2 | 1.526 (6) | O5—C7 | 1.253 (5) |
C2—N1 | 1.499 (6) | O6—C7 | 1.253 (5) |
C2—C3 | 1.521 (7) | C7—C8 | 1.529 (6) |
C2—H2 | 1.0000 | C8—N3 | 1.492 (6) |
C3—H3A | 0.9800 | C8—C9 | 1.526 (7) |
C3—H3B | 0.9800 | C8—H8 | 1.0000 |
C3—H3C | 0.9800 | C9—H9A | 0.9800 |
N1—H1N | 0.91 (3) | C9—H9B | 0.9800 |
N1—H2N | 0.91 (3) | C9—H9C | 0.9800 |
N1—H3N | 0.91 (3) | N3—H7N | 0.91 (3) |
O3—C4 | 1.257 (5) | N3—H8N | 0.92 (3) |
O4—C4 | 1.269 (6) | N3—H9N | 0.89 (3) |
O4—Mn1ii | 2.241 (3) | O1W—H1W | 0.81 (3) |
C4—C5 | 1.522 (6) | O1W—H2W | 0.81 (3) |
| | | |
O5—Mn1—O2 | 90.64 (14) | N2—C5—C6 | 111.0 (4) |
O5—Mn1—O1W | 80.07 (13) | N2—C5—C4 | 108.4 (4) |
O2—Mn1—O1W | 167.29 (13) | C6—C5—C4 | 111.4 (4) |
O5—Mn1—O1i | 95.19 (13) | N2—C5—H5 | 108.7 |
O2—Mn1—O1i | 83.55 (12) | C6—C5—H5 | 108.7 |
O1W—Mn1—O1i | 88.64 (12) | C4—C5—H5 | 108.7 |
O5—Mn1—O3 | 101.43 (13) | C5—C6—H6A | 109.5 |
O2—Mn1—O3 | 86.44 (12) | C5—C6—H6B | 109.5 |
O1W—Mn1—O3 | 103.80 (13) | H6A—C6—H6B | 109.5 |
O1i—Mn1—O3 | 160.67 (12) | C5—C6—H6C | 109.5 |
O5—Mn1—O4i | 164.57 (13) | H6A—C6—H6C | 109.5 |
O2—Mn1—O4i | 104.37 (13) | H6B—C6—H6C | 109.5 |
O1W—Mn1—O4i | 84.54 (12) | C5—N2—H4N | 113 (3) |
O1i—Mn1—O4i | 83.18 (12) | C5—N2—H5N | 105 (3) |
O3—Mn1—O4i | 83.35 (11) | H4N—N2—H5N | 111 (5) |
C1—O1—Mn1ii | 143.4 (3) | C5—N2—H6N | 113 (4) |
C1—O2—Mn1 | 127.7 (3) | H4N—N2—H6N | 107 (5) |
O1—C1—O2 | 126.8 (4) | H5N—N2—H6N | 108 (5) |
O1—C1—C2 | 118.5 (4) | C7—O5—Mn1 | 163.7 (3) |
O2—C1—C2 | 114.7 (4) | O6—C7—O5 | 127.3 (4) |
N1—C2—C3 | 109.8 (4) | O6—C7—C8 | 115.7 (4) |
N1—C2—C1 | 108.6 (4) | O5—C7—C8 | 117.0 (4) |
C3—C2—C1 | 110.9 (4) | N3—C8—C9 | 110.1 (4) |
N1—C2—H2 | 109.2 | N3—C8—C7 | 108.5 (4) |
C3—C2—H2 | 109.2 | C9—C8—C7 | 110.1 (4) |
C1—C2—H2 | 109.2 | N3—C8—H8 | 109.4 |
C2—C3—H3A | 109.5 | C9—C8—H8 | 109.4 |
C2—C3—H3B | 109.5 | C7—C8—H8 | 109.4 |
H3A—C3—H3B | 109.5 | C8—C9—H9A | 109.5 |
C2—C3—H3C | 109.5 | C8—C9—H9B | 109.5 |
H3A—C3—H3C | 109.5 | H9A—C9—H9B | 109.5 |
H3B—C3—H3C | 109.5 | C8—C9—H9C | 109.5 |
C2—N1—H1N | 107 (3) | H9A—C9—H9C | 109.5 |
C2—N1—H2N | 112 (3) | H9B—C9—H9C | 109.5 |
H1N—N1—H2N | 113 (5) | C8—N3—H7N | 105 (3) |
C2—N1—H3N | 111 (3) | C8—N3—H8N | 107 (3) |
H1N—N1—H3N | 108 (5) | H7N—N3—H8N | 107 (5) |
H2N—N1—H3N | 106 (5) | C8—N3—H9N | 108 (4) |
C4—O3—Mn1 | 136.8 (3) | H7N—N3—H9N | 117 (5) |
C4—O4—Mn1ii | 128.9 (3) | H8N—N3—H9N | 114 (5) |
O3—C4—O4 | 125.8 (4) | Mn1—O1W—H1W | 111 (4) |
O3—C4—C5 | 118.2 (4) | Mn1—O1W—H2W | 101 (4) |
O4—C4—C5 | 115.9 (4) | H1W—O1W—H2W | 103 (5) |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
Crystal data top
C9H23MnN3O7·2(I) | Z = 2 |
Mr = 594.04 | F(000) = 570 |
Monoclinic, P21 | Dx = 2.130 Mg m−3 |
a = 4.7932 (16) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 16.261 (5) Å | µ = 4.08 mm−1 |
c = 11.894 (4) Å | T = 100 K |
β = 92.255 (6)° | Needle, colourless |
V = 926.3 (5) Å3 | 0.12 × 0.04 × 0.04 mm |
Data collection top
Bruker APEX CCD diffractometer | 3762 independent reflections |
Radiation source: microsource | 3371 reflections with I > 2σ(I) |
Multilayer optics monochromator | Rint = 0.069 |
ω scans | θmax = 26.4°, θmin = 2.5° |
Absorption correction: multi-scan SADABS | h = −5→5 |
Tmin = 0.588, Tmax = 0.745 | k = −20→20 |
10911 measured reflections | l = −14→14 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 1.01 | Δρmax = 1.59 e Å−3 |
3762 reflections | Δρmin = −1.04 e Å−3 |
235 parameters | Absolute structure: Flack x determined using 1417 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61). |
30 restraints | Absolute structure parameter: −0.03 (4) |
Crystal data top
C9H23MnN3O7·2(I) | V = 926.3 (5) Å3 |
Mr = 594.04 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 4.7932 (16) Å | µ = 4.08 mm−1 |
b = 16.261 (5) Å | T = 100 K |
c = 11.894 (4) Å | 0.12 × 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 = 0.745 | Rint = 0.069 |
10911 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.099 | Δρmax = 1.59 e Å−3 |
S = 1.01 | Δρmin = −1.04 e Å−3 |
3762 reflections | Absolute structure: Flack x determined using 1417 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61). |
235 parameters | Absolute 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 | x | y | z | Uiso*/Ueq | |
Mn1 | 0.9199 (5) | 0.74999 (13) | 0.06440 (18) | 0.0125 (4) | |
I1 | 0.76587 (17) | 0.37006 (5) | 0.31903 (7) | 0.0167 (2) | |
I2 | 0.61347 (18) | 0.64837 (5) | 0.46242 (7) | 0.0185 (2) | |
O1W | 1.167 (2) | 0.8625 (7) | 0.0408 (8) | 0.017 (2) | |
H2W | 1.23 (3) | 0.866 (11) | 0.108 (5) | 0.020* | |
H1W | 1.29 (2) | 0.838 (8) | 0.004 (11) | 0.020* | |
O1 | 0.2765 (19) | 0.6959 (5) | 0.1573 (8) | 0.016 (2) | |
O2 | 0.6941 (18) | 0.6409 (6) | 0.1214 (8) | 0.015 (2) | |
C1 | 0.450 (3) | 0.6381 (8) | 0.1546 (11) | 0.017 (3) | |
C2 | 0.357 (3) | 0.5515 (8) | 0.1927 (12) | 0.012 (3) | |
H2 | 0.5123 | 0.5251 | 0.2385 | 0.014* | |
C3 | 0.281 (4) | 0.4975 (9) | 0.0913 (12) | 0.024 (3) | |
H3A | 0.2415 | 0.4415 | 0.1167 | 0.035* | |
H3B | 0.4375 | 0.4963 | 0.0406 | 0.035* | |
H3C | 0.1156 | 0.5200 | 0.0513 | 0.035* | |
N1 | 0.737 (2) | 0.7153 (7) | −0.2601 (10) | 0.014 (2) | |
H1N | 0.894 (18) | 0.708 (9) | −0.214 (10) | 0.017* | |
H2N | 0.68 (3) | 0.768 (3) | −0.272 (12) | 0.017* | |
H3N | 0.75 (3) | 0.692 (9) | −0.330 (6) | 0.017* | |
O3 | 0.571 (2) | 0.7637 (6) | −0.0602 (8) | 0.0145 (19) | |
O4 | 0.1481 (19) | 0.7036 (6) | −0.0846 (7) | 0.0127 (19) | |
C4 | 0.396 (3) | 0.7169 (8) | −0.1107 (10) | 0.011 (3) | |
C5 | 0.498 (3) | 0.6700 (8) | −0.2133 (12) | 0.018 (3) | |
H5 | 0.3427 | 0.6674 | −0.2719 | 0.022* | |
C6 | 0.582 (3) | 0.5826 (8) | −0.1801 (12) | 0.019 (3) | |
H6A | 0.6473 | 0.5534 | −0.2461 | 0.028* | |
H6B | 0.4208 | 0.5538 | −0.1508 | 0.028* | |
H6C | 0.7326 | 0.5846 | −0.1219 | 0.028* | |
N2 | 0.107 (3) | 0.5610 (7) | 0.2631 (10) | 0.016 (2) | |
H4N | 0.03 (3) | 0.510 (4) | 0.268 (12) | 0.019* | |
H5N | 0.01 (3) | 0.599 (7) | 0.220 (10) | 0.019* | |
H6N | 0.14 (3) | 0.589 (8) | 0.329 (7) | 0.019* | |
O5 | 0.790 (2) | 0.8190 (6) | 0.1996 (8) | 0.018 (2) | |
O6 | 0.4015 (18) | 0.8845 (6) | 0.2518 (7) | 0.016 (2) | |
C7 | 0.644 (3) | 0.8565 (8) | 0.2698 (11) | 0.016 (3) | |
C8 | 0.771 (2) | 0.8721 (9) | 0.3869 (11) | 0.016 (3) | |
H8 | 0.6355 | 0.8566 | 0.4451 | 0.019* | |
C9 | 0.852 (3) | 0.9633 (9) | 0.3997 (13) | 0.024 (3) | |
H9A | 0.9408 | 0.9724 | 0.4743 | 0.035* | |
H9B | 0.6846 | 0.9975 | 0.3910 | 0.035* | |
H9C | 0.9835 | 0.9781 | 0.3418 | 0.035* | |
N3 | 1.028 (3) | 0.8214 (8) | 0.4007 (11) | 0.019 (3) | |
H7N | 1.07 (3) | 0.826 (10) | 0.477 (4) | 0.023* | |
H8N | 1.17 (2) | 0.842 (8) | 0.356 (11) | 0.023* | |
H9N | 1.01 (3) | 0.766 (2) | 0.392 (12) | 0.023* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Mn1 | 0.0096 (9) | 0.0112 (10) | 0.0170 (10) | 0.0005 (8) | 0.0013 (7) | −0.0004 (8) |
I1 | 0.0164 (5) | 0.0110 (4) | 0.0227 (5) | −0.0013 (4) | −0.0009 (3) | 0.0011 (4) |
I2 | 0.0197 (5) | 0.0162 (4) | 0.0197 (5) | −0.0042 (4) | 0.0009 (3) | −0.0017 (4) |
O1W | 0.017 (5) | 0.014 (5) | 0.020 (5) | 0.001 (5) | 0.001 (4) | −0.001 (5) |
O1 | 0.013 (5) | 0.009 (5) | 0.026 (5) | 0.003 (4) | 0.004 (4) | 0.002 (4) |
O2 | 0.011 (5) | 0.012 (5) | 0.023 (5) | −0.001 (4) | 0.003 (4) | 0.000 (4) |
C1 | 0.018 (7) | 0.009 (7) | 0.023 (7) | −0.004 (6) | 0.003 (6) | −0.002 (6) |
C2 | 0.005 (6) | 0.010 (7) | 0.021 (7) | −0.002 (5) | 0.005 (5) | 0.003 (5) |
C3 | 0.035 (9) | 0.014 (8) | 0.021 (8) | −0.003 (7) | 0.003 (7) | 0.001 (6) |
N1 | 0.010 (6) | 0.012 (6) | 0.020 (6) | 0.001 (5) | −0.004 (5) | −0.001 (5) |
O3 | 0.012 (5) | 0.010 (4) | 0.021 (5) | −0.001 (4) | 0.000 (4) | −0.005 (4) |
O4 | 0.012 (5) | 0.015 (5) | 0.012 (5) | 0.005 (4) | 0.003 (4) | −0.004 (4) |
C4 | 0.009 (7) | 0.013 (7) | 0.011 (6) | 0.003 (5) | 0.003 (5) | 0.003 (5) |
C5 | 0.012 (7) | 0.019 (8) | 0.023 (8) | −0.002 (6) | 0.002 (6) | −0.004 (6) |
C6 | 0.020 (8) | 0.010 (7) | 0.026 (8) | 0.002 (6) | 0.002 (6) | −0.004 (6) |
N2 | 0.017 (7) | 0.010 (6) | 0.020 (6) | −0.002 (5) | 0.001 (5) | 0.001 (5) |
O5 | 0.013 (5) | 0.019 (5) | 0.022 (5) | −0.001 (4) | 0.005 (4) | 0.000 (4) |
O6 | 0.012 (5) | 0.015 (5) | 0.020 (5) | −0.001 (4) | 0.002 (4) | 0.001 (4) |
C7 | 0.011 (5) | 0.017 (6) | 0.020 (5) | −0.008 (4) | 0.003 (4) | 0.002 (5) |
C8 | 0.008 (5) | 0.017 (5) | 0.023 (5) | 0.001 (5) | 0.001 (4) | 0.002 (5) |
C9 | 0.029 (8) | 0.015 (7) | 0.025 (7) | 0.000 (6) | −0.013 (6) | −0.008 (6) |
N3 | 0.018 (7) | 0.016 (6) | 0.022 (7) | 0.005 (5) | 0.005 (5) | 0.004 (5) |
Geometric parameters (Å, º) top
Mn1—O5 | 2.077 (10) | O4—C4 | 1.259 (15) |
Mn1—O1i | 2.183 (9) | O4—Mn1ii | 2.249 (9) |
Mn1—O2 | 2.199 (10) | C4—C5 | 1.536 (18) |
Mn1—O3 | 2.202 (10) | C5—C6 | 1.52 (2) |
Mn1—O1W | 2.202 (11) | C5—H5 | 1.0000 |
Mn1—O4i | 2.249 (9) | C6—H6A | 0.9800 |
O1W—H2W | 0.84 (3) | C6—H6B | 0.9800 |
O1W—H1W | 0.84 (3) | C6—H6C | 0.9800 |
O1—C1 | 1.256 (16) | N2—H4N | 0.92 (3) |
O1—Mn1ii | 2.183 (9) | N2—H5N | 0.92 (3) |
O2—C1 | 1.252 (16) | N2—H6N | 0.92 (3) |
C1—C2 | 1.549 (18) | O5—C7 | 1.268 (16) |
C2—N2 | 1.496 (18) | O6—C7 | 1.258 (16) |
C2—C3 | 1.52 (2) | C7—C8 | 1.520 (18) |
C2—H2 | 1.0000 | C8—N3 | 1.485 (18) |
C3—H3A | 0.9800 | C8—C9 | 1.54 (2) |
C3—H3B | 0.9800 | C8—H8 | 1.0000 |
C3—H3C | 0.9800 | C9—H9A | 0.9800 |
N1—C5 | 1.488 (18) | C9—H9B | 0.9800 |
N1—H1N | 0.92 (3) | C9—H9C | 0.9800 |
N1—H2N | 0.91 (3) | N3—H7N | 0.92 (3) |
N1—H3N | 0.92 (3) | N3—H8N | 0.92 (3) |
O3—C4 | 1.265 (16) | N3—H9N | 0.91 (3) |
| | | |
O5—Mn1—O1i | 94.5 (4) | O4—C4—O3 | 126.9 (12) |
O5—Mn1—O2 | 91.8 (4) | O4—C4—C5 | 116.3 (11) |
O1i—Mn1—O2 | 84.5 (3) | O3—C4—C5 | 116.8 (11) |
O5—Mn1—O3 | 103.0 (4) | N1—C5—C6 | 111.0 (12) |
O1i—Mn1—O3 | 160.1 (4) | N1—C5—C4 | 108.9 (11) |
O2—Mn1—O3 | 85.4 (4) | C6—C5—C4 | 110.2 (11) |
O5—Mn1—O1W | 80.1 (4) | N1—C5—H5 | 108.9 |
O1i—Mn1—O1W | 89.2 (4) | C6—C5—H5 | 108.9 |
O2—Mn1—O1W | 169.3 (4) | C4—C5—H5 | 108.9 |
O3—Mn1—O1W | 103.1 (4) | C5—C6—H6A | 109.5 |
O5—Mn1—O4i | 164.0 (4) | C5—C6—H6B | 109.5 |
O1i—Mn1—O4i | 82.4 (4) | H6A—C6—H6B | 109.5 |
O2—Mn1—O4i | 103.5 (3) | C5—C6—H6C | 109.5 |
O3—Mn1—O4i | 83.3 (3) | H6A—C6—H6C | 109.5 |
O1W—Mn1—O4i | 84.1 (3) | H6B—C6—H6C | 109.5 |
Mn1—O1W—H2W | 96 (10) | C2—N2—H4N | 107 (9) |
Mn1—O1W—H1W | 93 (10) | C2—N2—H5N | 100 (9) |
H2W—O1W—H1W | 108 (10) | H4N—N2—H5N | 116 (10) |
C1—O1—Mn1ii | 142.6 (9) | C2—N2—H6N | 114 (9) |
C1—O2—Mn1 | 127.2 (9) | H4N—N2—H6N | 117 (10) |
O2—C1—O1 | 127.5 (13) | H5N—N2—H6N | 102 (10) |
O2—C1—C2 | 114.1 (12) | C7—O5—Mn1 | 163.8 (9) |
O1—C1—C2 | 118.4 (12) | O6—C7—O5 | 126.4 (12) |
N2—C2—C3 | 109.3 (12) | O6—C7—C8 | 115.5 (12) |
N2—C2—C1 | 108.3 (11) | O5—C7—C8 | 118.1 (12) |
C3—C2—C1 | 110.7 (11) | N3—C8—C7 | 108.1 (11) |
N2—C2—H2 | 109.5 | N3—C8—C9 | 108.6 (11) |
C3—C2—H2 | 109.5 | C7—C8—C9 | 109.9 (11) |
C1—C2—H2 | 109.5 | N3—C8—H8 | 110.1 |
C2—C3—H3A | 109.5 | C7—C8—H8 | 110.1 |
C2—C3—H3B | 109.5 | C9—C8—H8 | 110.1 |
H3A—C3—H3B | 109.5 | C8—C9—H9A | 109.5 |
C2—C3—H3C | 109.5 | C8—C9—H9B | 109.5 |
H3A—C3—H3C | 109.5 | H9A—C9—H9B | 109.5 |
H3B—C3—H3C | 109.5 | C8—C9—H9C | 109.5 |
C5—N1—H1N | 110 (9) | H9A—C9—H9C | 109.5 |
C5—N1—H2N | 107 (10) | H9B—C9—H9C | 109.5 |
H1N—N1—H2N | 117 (10) | C8—N3—H7N | 101 (10) |
C5—N1—H3N | 103 (10) | C8—N3—H8N | 110 (10) |
H1N—N1—H3N | 113 (10) | H7N—N3—H8N | 115 (10) |
H2N—N1—H3N | 106 (10) | C8—N3—H9N | 119 (10) |
C4—O3—Mn1 | 136.9 (9) | H7N—N3—H9N | 102 (10) |
C4—O4—Mn1ii | 129.0 (8) | H8N—N3—H9N | 110 (10) |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
Crystal data top
C6H18CaN2O6·2(Cl)·H2O | F(000) = 720 |
Mr = 343.22 | Dx = 1.518 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
a = 23.347 (7) Å | µ = 0.80 mm−1 |
b = 8.702 (3) Å | T = 100 K |
c = 7.391 (2) Å | Needle, colourless |
V = 1501.5 (8) Å3 | 0.20 × 0.08 × 0.04 mm |
Z = 4 | |
Data collection top
Bruker APEX CCD diffractometer | 1545 independent reflections |
Radiation source: microsource | 1164 reflections with I > 2σ(I) |
Multi-layer optics monochromator | Rint = 0.129 |
ω scans | θmax = 26.4°, θmin = 2.5° |
Absorption correction: multi-scan SADABS | h = −29→29 |
Tmin = 0.571, Tmax = 0.745 | k = −10→10 |
16504 measured reflections | l = −9→9 |
Refinement top
Refinement on F2 | 6 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.037 | H 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 reflections | Δρmax = 0.34 e Å−3 |
102 parameters | Δρmin = −0.31 e Å−3 |
Crystal data top
C6H18CaN2O6·2(Cl)·H2O | V = 1501.5 (8) Å3 |
Mr = 343.22 | Z = 4 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 23.347 (7) Å | µ = 0.80 mm−1 |
b = 8.702 (3) Å | T = 100 K |
c = 7.391 (2) Å | 0.20 × 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 = 0.745 | Rint = 0.129 |
16504 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.037 | 6 restraints |
wR(F2) = 0.083 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.34 e Å−3 |
1545 reflections | Δρmin = −0.31 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Ca1 | 0.5000 | 0.59494 (8) | 0.2500 | 0.01290 (19) | |
Cl1 | 0.68892 (3) | 0.73248 (7) | 0.05715 (9) | 0.01771 (18) | |
O1 | 0.59104 (7) | 0.4699 (2) | 0.2517 (3) | 0.0224 (5) | |
O2 | 0.53781 (8) | 0.3579 (2) | 0.0429 (2) | 0.0208 (4) | |
C1 | 0.58538 (11) | 0.3843 (3) | 0.1180 (4) | 0.0160 (6) | |
C2 | 0.63906 (11) | 0.3070 (3) | 0.0425 (4) | 0.0164 (6) | |
H2 | 0.6427 | 0.3342 | −0.0885 | 0.020* | |
C3 | 0.63797 (12) | 0.1331 (3) | 0.0599 (4) | 0.0225 (6) | |
H3A | 0.6727 | 0.0899 | 0.0053 | 0.034* | |
H3B | 0.6042 | 0.0924 | −0.0025 | 0.034* | |
H3C | 0.6364 | 0.1047 | 0.1881 | 0.034* | |
N1 | 0.68928 (9) | 0.3709 (3) | 0.1413 (3) | 0.0165 (5) | |
H1A | 0.6865 (11) | 0.353 (3) | 0.264 (2) | 0.020* | |
H1B | 0.6908 (11) | 0.475 (2) | 0.125 (4) | 0.020* | |
H1C | 0.7220 (9) | 0.324 (3) | 0.096 (4) | 0.020* | |
O1W | 0.55648 (8) | 0.8059 (2) | 0.1368 (3) | 0.0250 (5) | |
H3E | 0.5900 (8) | 0.793 (3) | 0.117 (4) | 0.030* | |
H3D | 0.5480 (13) | 0.892 (2) | 0.175 (4) | 0.030* | |
O2W | 0.5000 | 1.0793 (3) | 0.2500 | 0.0352 (8) | |
H4 | 0.4958 (15) | 1.137 (3) | 0.160 (3) | 0.042* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ca1 | 0.0082 (4) | 0.0166 (4) | 0.0139 (4) | 0.000 | 0.0001 (3) | 0.000 |
Cl1 | 0.0119 (3) | 0.0200 (3) | 0.0212 (4) | −0.0023 (3) | −0.0005 (3) | −0.0010 (3) |
O1 | 0.0129 (10) | 0.0248 (10) | 0.0296 (12) | 0.0022 (8) | 0.0019 (9) | −0.0079 (9) |
O2 | 0.0107 (10) | 0.0335 (11) | 0.0181 (10) | −0.0006 (8) | −0.0015 (8) | 0.0061 (9) |
C1 | 0.0136 (14) | 0.0177 (13) | 0.0166 (14) | −0.0002 (11) | 0.0018 (11) | 0.0090 (11) |
C2 | 0.0142 (14) | 0.0198 (14) | 0.0152 (14) | 0.0008 (10) | −0.0008 (11) | −0.0001 (11) |
C3 | 0.0201 (15) | 0.0185 (14) | 0.0290 (17) | 0.0016 (11) | −0.0021 (13) | −0.0002 (13) |
N1 | 0.0099 (11) | 0.0185 (12) | 0.0212 (13) | 0.0002 (9) | 0.0009 (11) | 0.0002 (11) |
O1W | 0.0126 (10) | 0.0196 (10) | 0.0426 (14) | −0.0007 (9) | 0.0077 (10) | −0.0007 (10) |
O2W | 0.055 (2) | 0.0203 (17) | 0.0306 (19) | 0.000 | 0.0203 (18) | 0.000 |
Geometric parameters (Å, º) top
Ca1—O2i | 2.3732 (19) | O2—Ca1ii | 2.3732 (19) |
Ca1—O2ii | 2.3732 (19) | C1—C2 | 1.528 (4) |
Ca1—O1iii | 2.3880 (18) | C2—N1 | 1.489 (3) |
Ca1—O1 | 2.3880 (18) | C2—C3 | 1.519 (3) |
Ca1—O1W | 2.410 (2) | C2—H2 | 1.0000 |
Ca1—O1Wiii | 2.410 (2) | C3—H3A | 0.9800 |
Ca1—O2 | 2.716 (2) | C3—H3B | 0.9800 |
Ca1—O2iii | 2.716 (2) | C3—H3C | 0.9800 |
Ca1—C1iii | 2.879 (3) | N1—H1A | 0.922 (17) |
Ca1—C1 | 2.879 (3) | N1—H1B | 0.917 (17) |
Ca1—Ca1ii | 4.0479 (12) | N1—H1C | 0.927 (17) |
Ca1—Ca1iv | 4.0479 (12) | O1W—H3E | 0.805 (17) |
O1—C1 | 1.245 (3) | O1W—H3D | 0.825 (17) |
O2—C1 | 1.263 (3) | O2W—H4 | 0.840 (17) |
| | | |
O2i—Ca1—O2ii | 160.10 (10) | O1W—Ca1—Ca1ii | 89.66 (6) |
O2i—Ca1—O1iii | 114.50 (7) | O1Wiii—Ca1—Ca1ii | 128.89 (6) |
O2ii—Ca1—O1iii | 75.10 (6) | O2—Ca1—Ca1ii | 34.46 (4) |
O2i—Ca1—O1 | 75.10 (6) | O2iii—Ca1—Ca1ii | 101.81 (5) |
O2ii—Ca1—O1 | 114.50 (7) | C1iii—Ca1—Ca1ii | 92.83 (6) |
O1iii—Ca1—O1 | 125.78 (9) | C1—Ca1—Ca1ii | 55.29 (6) |
O2i—Ca1—O1W | 88.93 (7) | O2i—Ca1—Ca1iv | 40.36 (5) |
O2ii—Ca1—O1W | 75.84 (7) | O2ii—Ca1—Ca1iv | 154.57 (5) |
O1iii—Ca1—O1W | 146.33 (7) | O1iii—Ca1—Ca1iv | 79.56 (5) |
O1—Ca1—O1W | 82.07 (7) | O1—Ca1—Ca1iv | 79.00 (5) |
O2i—Ca1—O1Wiii | 75.84 (7) | O1W—Ca1—Ca1iv | 128.89 (6) |
O2ii—Ca1—O1Wiii | 88.93 (7) | O1Wiii—Ca1—Ca1iv | 89.66 (6) |
O1iii—Ca1—O1Wiii | 82.07 (7) | O2—Ca1—Ca1iv | 101.81 (5) |
O1—Ca1—O1Wiii | 146.33 (7) | O2iii—Ca1—Ca1iv | 34.46 (4) |
O1W—Ca1—O1Wiii | 80.77 (10) | C1iii—Ca1—Ca1iv | 55.29 (6) |
O2i—Ca1—O2 | 121.63 (6) | C1—Ca1—Ca1iv | 92.83 (6) |
O2ii—Ca1—O2 | 74.81 (7) | Ca1ii—Ca1—Ca1iv | 131.82 (4) |
O1iii—Ca1—O2 | 86.58 (6) | C1—O1—Ca1 | 100.03 (16) |
O1—Ca1—O2 | 50.77 (6) | C1—O2—Ca1ii | 134.18 (17) |
O1W—Ca1—O2 | 101.83 (7) | C1—O2—Ca1 | 84.27 (16) |
O1Wiii—Ca1—O2 | 162.15 (7) | Ca1ii—O2—Ca1 | 105.19 (7) |
O2i—Ca1—O2iii | 74.81 (7) | O1—C1—O2 | 123.5 (2) |
O2ii—Ca1—O2iii | 121.63 (6) | O1—C1—C2 | 117.8 (2) |
O1iii—Ca1—O2iii | 50.77 (6) | O2—C1—C2 | 118.8 (2) |
O1—Ca1—O2iii | 86.58 (6) | O1—C1—Ca1 | 54.78 (13) |
O1W—Ca1—O2iii | 162.15 (7) | O2—C1—Ca1 | 69.85 (15) |
O1Wiii—Ca1—O2iii | 101.83 (7) | C2—C1—Ca1 | 166.44 (18) |
O2—Ca1—O2iii | 81.18 (8) | N1—C2—C3 | 110.1 (2) |
O2i—Ca1—C1iii | 93.36 (7) | N1—C2—C1 | 107.6 (2) |
O2ii—Ca1—C1iii | 99.30 (7) | C3—C2—C1 | 113.2 (2) |
O1iii—Ca1—C1iii | 25.20 (7) | N1—C2—H2 | 108.6 |
O1—Ca1—C1iii | 108.93 (8) | C3—C2—H2 | 108.6 |
O1W—Ca1—C1iii | 168.99 (7) | C1—C2—H2 | 108.6 |
O1Wiii—Ca1—C1iii | 89.35 (7) | C2—C3—H3A | 109.5 |
O2—Ca1—C1iii | 86.13 (7) | C2—C3—H3B | 109.5 |
O2iii—Ca1—C1iii | 25.88 (6) | H3A—C3—H3B | 109.5 |
O2i—Ca1—C1 | 99.30 (7) | C2—C3—H3C | 109.5 |
O2ii—Ca1—C1 | 93.36 (7) | H3A—C3—H3C | 109.5 |
O1iii—Ca1—C1 | 108.93 (8) | H3B—C3—H3C | 109.5 |
O1—Ca1—C1 | 25.20 (7) | C2—N1—H1A | 111.4 (17) |
O1W—Ca1—C1 | 89.35 (7) | C2—N1—H1B | 109.5 (16) |
O1Wiii—Ca1—C1 | 168.99 (7) | H1A—N1—H1B | 107 (2) |
O2—Ca1—C1 | 25.88 (6) | C2—N1—H1C | 107.9 (18) |
O2iii—Ca1—C1 | 86.13 (7) | H1A—N1—H1C | 110 (2) |
C1iii—Ca1—C1 | 100.88 (11) | H1B—N1—H1C | 111 (2) |
O2i—Ca1—Ca1ii | 154.57 (5) | Ca1—O1W—H3E | 119 (2) |
O2ii—Ca1—Ca1ii | 40.36 (5) | Ca1—O1W—H3D | 116 (2) |
O1iii—Ca1—Ca1ii | 79.00 (5) | H3E—O1W—H3D | 115 (3) |
O1—Ca1—Ca1ii | 79.56 (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. |
Crystal data top
C9H23CaN3O7·2(Br) | F(000) = 976 |
Mr = 485.20 | Dx = 1.779 Mg m−3 |
Orthorhombic, Pc21n | Mo Kα radiation, λ = 0.71073 Å |
a = 4.8727 (5) Å | µ = 4.79 mm−1 |
b = 16.0701 (17) Å | T = 100 K |
c = 23.129 (2) Å | Needle, colourless |
V = 1811.1 (3) Å3 | 0.50 × 0.09 × 0.07 mm |
Z = 4 | |
Data collection top
Bruker APEX CCD diffractometer | 3739 independent reflections |
Radiation source: microsource | 3450 reflections with I > 2σ(I) |
Multilayer optics monochromator | Rint = 0.060 |
ω scans | θmax = 26.5°, θmin = 2.2° |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | h = −6→6 |
Tmin = 0.437, Tmax = 0.745 | k = −20→20 |
20251 measured reflections | l = −29→28 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 1.03 | Δρmax = 1.06 e Å−3 |
3739 reflections | Δρmin = −0.30 e Å−3 |
234 parameters | Absolute structure: Flack x determined using 1545 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61). |
38 restraints | Absolute structure parameter: 0.004 (6) |
Crystal data top
C9H23CaN3O7·2(Br) | V = 1811.1 (3) Å3 |
Mr = 485.20 | Z = 4 |
Orthorhombic, Pc21n | Mo Kα radiation |
a = 4.8727 (5) Å | µ = 4.79 mm−1 |
b = 16.0701 (17) Å | T = 100 K |
c = 23.129 (2) Å | 0.50 × 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 = 0.745 | Rint = 0.060 |
20251 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.062 | Δρmax = 1.06 e Å−3 |
S = 1.03 | Δρmin = −0.30 e Å−3 |
3739 reflections | Absolute structure: Flack x determined using 1545 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61). |
234 parameters | Absolute 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 | x | y | z | Uiso*/Ueq | |
Ca1 | 0.9085 (2) | 0.75000 (6) | 0.03355 (4) | 0.0096 (2) | |
Br1 | 0.57417 (12) | 0.65284 (4) | 0.23125 (2) | 0.02133 (15) | |
Br2 | 0.75563 (10) | 0.36823 (4) | 0.16347 (2) | 0.01238 (12) | |
O5 | 0.7433 (7) | 0.8303 (2) | 0.10495 (16) | 0.0144 (8) | |
O6 | 0.3528 (7) | 0.8887 (2) | 0.13480 (16) | 0.0137 (8) | |
O1W | 1.1826 (7) | 0.8715 (3) | 0.02281 (15) | 0.0133 (8) | |
H1W | 1.237 (11) | 0.878 (4) | 0.0532 (19) | 0.016* | |
H2W | 1.314 (9) | 0.859 (4) | 0.008 (2) | 0.016* | |
N3 | 0.9651 (10) | 0.8216 (3) | 0.2085 (2) | 0.0139 (10) | |
H9N | 1.082 (10) | 0.834 (4) | 0.1796 (19) | 0.017* | |
H7N | 1.045 (12) | 0.830 (4) | 0.2435 (15) | 0.017* | |
H8N | 0.925 (12) | 0.7672 (19) | 0.210 (3) | 0.017* | |
C9 | 0.7680 (13) | 0.9621 (4) | 0.2169 (3) | 0.0200 (13) | |
H9C | 0.8926 | 0.9846 | 0.1876 | 0.024* | |
H9A | 0.8538 | 0.9664 | 0.2551 | 0.024* | |
H9B | 0.5961 | 0.9937 | 0.2166 | 0.024* | |
C8 | 0.7081 (10) | 0.8714 (4) | 0.2036 (2) | 0.0131 (10) | |
H8A | 0.5711 | 0.8499 | 0.2322 | 0.016* | |
C7 | 0.5909 (10) | 0.8621 (3) | 0.1428 (2) | 0.0126 (11) | |
O4 | 0.1499 (8) | 0.7049 (2) | −0.05102 (16) | 0.0135 (8) | |
O3 | 0.5612 (7) | 0.7625 (2) | −0.03518 (15) | 0.0123 (8) | |
C4 | 0.3979 (11) | 0.7181 (3) | −0.0636 (2) | 0.0106 (11) | |
C5 | 0.5094 (11) | 0.6740 (3) | −0.1170 (2) | 0.0114 (11) | |
H5A | 0.3634 | 0.6718 | −0.1474 | 0.014* | |
C6 | 0.5979 (13) | 0.5859 (4) | −0.1017 (3) | 0.0198 (13) | |
H6C | 0.7363 | 0.5879 | −0.0710 | 0.024* | |
H6A | 0.6759 | 0.5590 | −0.1360 | 0.024* | |
H6B | 0.4384 | 0.5542 | −0.0883 | 0.024* | |
N2 | 0.7484 (9) | 0.7226 (3) | −0.1392 (2) | 0.0118 (10) | |
H5N | 0.792 (11) | 0.700 (4) | −0.1735 (16) | 0.014* | |
H6N | 0.724 (11) | 0.7780 (18) | −0.142 (3) | 0.014* | |
H4N | 0.881 (9) | 0.718 (4) | −0.113 (2) | 0.014* | |
N1 | 0.0739 (10) | 0.5555 (3) | 0.1412 (2) | 0.0134 (10) | |
H2N | −0.062 (9) | 0.578 (3) | 0.120 (2) | 0.016* | |
H3N | −0.015 (11) | 0.510 (3) | 0.153 (2) | 0.016* | |
H1N | 0.095 (12) | 0.591 (3) | 0.1719 (18) | 0.016* | |
C1 | 0.4265 (12) | 0.6279 (3) | 0.0851 (2) | 0.0122 (11) | |
C2 | 0.3281 (11) | 0.5436 (3) | 0.1058 (2) | 0.0116 (11) | |
H2A | 0.4736 | 0.5170 | 0.1300 | 0.014* | |
C3 | 0.2614 (13) | 0.4877 (4) | 0.0546 (3) | 0.0215 (13) | |
H3A | 0.1986 | 0.4334 | 0.0687 | 0.032* | |
H3B | 0.4261 | 0.4802 | 0.0308 | 0.032* | |
H3C | 0.1164 | 0.5134 | 0.0313 | 0.032* | |
O1 | 0.2600 (7) | 0.6863 (2) | 0.08266 (16) | 0.0133 (8) | |
O2 | 0.6762 (7) | 0.6311 (2) | 0.06906 (16) | 0.0137 (8) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ca1 | 0.0092 (5) | 0.0100 (5) | 0.0097 (5) | 0.0005 (4) | 0.0002 (4) | 0.0002 (4) |
Br1 | 0.0315 (3) | 0.0188 (3) | 0.0137 (3) | −0.0106 (3) | −0.0023 (2) | −0.0011 (2) |
Br2 | 0.0130 (2) | 0.0112 (2) | 0.0130 (2) | −0.0009 (2) | 0.0007 (2) | 0.0008 (2) |
O5 | 0.012 (2) | 0.0183 (19) | 0.0125 (19) | 0.0013 (16) | 0.0015 (16) | −0.0042 (16) |
O6 | 0.0122 (19) | 0.014 (2) | 0.0153 (19) | 0.0006 (15) | 0.0012 (16) | −0.0010 (15) |
O1W | 0.012 (2) | 0.0174 (19) | 0.0102 (18) | −0.0015 (19) | −0.0001 (14) | −0.001 (2) |
N3 | 0.013 (3) | 0.016 (2) | 0.012 (2) | −0.001 (2) | −0.002 (2) | −0.001 (2) |
C9 | 0.025 (4) | 0.015 (3) | 0.020 (3) | 0.000 (2) | −0.006 (3) | −0.006 (2) |
C8 | 0.012 (3) | 0.015 (3) | 0.012 (2) | 0.001 (3) | 0.000 (2) | −0.002 (3) |
C7 | 0.014 (3) | 0.010 (2) | 0.013 (3) | −0.003 (3) | 0.003 (2) | 0.000 (2) |
O4 | 0.010 (2) | 0.018 (2) | 0.0126 (19) | 0.0009 (15) | −0.0006 (16) | −0.0019 (15) |
O3 | 0.012 (2) | 0.0126 (19) | 0.0117 (18) | 0.0007 (16) | −0.0012 (16) | −0.0010 (15) |
C4 | 0.010 (3) | 0.010 (2) | 0.012 (3) | 0.004 (2) | 0.000 (2) | 0.003 (2) |
C5 | 0.007 (3) | 0.015 (3) | 0.012 (2) | −0.0006 (19) | 0.002 (2) | −0.003 (2) |
C6 | 0.021 (3) | 0.011 (3) | 0.027 (3) | −0.001 (2) | 0.007 (3) | −0.005 (2) |
N2 | 0.012 (3) | 0.014 (2) | 0.009 (2) | 0.000 (2) | 0.0017 (19) | −0.0019 (19) |
N1 | 0.012 (2) | 0.013 (2) | 0.015 (2) | −0.002 (2) | 0.003 (2) | 0.0030 (19) |
C1 | 0.011 (3) | 0.016 (3) | 0.010 (2) | −0.003 (2) | −0.004 (2) | −0.003 (2) |
C2 | 0.005 (3) | 0.010 (3) | 0.019 (3) | 0.000 (2) | 0.000 (2) | 0.002 (2) |
C3 | 0.025 (4) | 0.018 (3) | 0.020 (3) | −0.005 (3) | 0.002 (3) | −0.004 (3) |
O1 | 0.0090 (19) | 0.0127 (19) | 0.018 (2) | 0.0012 (15) | −0.0039 (16) | 0.0032 (15) |
O2 | 0.0089 (19) | 0.015 (2) | 0.0173 (19) | −0.0008 (14) | 0.0015 (15) | 0.0046 (16) |
Geometric parameters (Å, º) top
Ca1—O5 | 2.245 (4) | O3—C4 | 1.254 (6) |
Ca1—O1i | 2.296 (4) | C4—C5 | 1.524 (7) |
Ca1—O3 | 2.331 (4) | C5—N2 | 1.493 (7) |
Ca1—O2 | 2.367 (4) | C5—C6 | 1.521 (8) |
Ca1—O1W | 2.379 (4) | C5—H5A | 1.0000 |
Ca1—O4i | 2.395 (4) | C6—H6C | 0.9800 |
Ca1—H1W | 2.64 (6) | C6—H6A | 0.9800 |
Ca1—H2W | 2.71 (6) | C6—H6B | 0.9800 |
O5—C7 | 1.257 (6) | N2—H5N | 0.90 (3) |
O6—C7 | 1.250 (6) | N2—H6N | 0.90 (3) |
O1W—H1W | 0.76 (4) | N2—H4N | 0.89 (3) |
O1W—H2W | 0.75 (4) | N1—C2 | 1.497 (7) |
N3—C8 | 1.491 (7) | N1—H2N | 0.90 (3) |
N3—H9N | 0.90 (3) | N1—H3N | 0.90 (3) |
N3—H7N | 0.91 (3) | N1—H1N | 0.91 (3) |
N3—H8N | 0.90 (3) | C1—O1 | 1.242 (7) |
C9—C8 | 1.518 (8) | C1—O2 | 1.273 (7) |
C9—H9C | 0.9800 | C1—C2 | 1.515 (7) |
C9—H9A | 0.9800 | C2—C3 | 1.522 (8) |
C9—H9B | 0.9800 | C2—H2A | 1.0000 |
C8—C7 | 1.526 (7) | C3—H3A | 0.9800 |
C8—H8A | 1.0000 | C3—H3B | 0.9800 |
O4—C4 | 1.261 (6) | C3—H3C | 0.9800 |
O4—Ca1ii | 2.395 (4) | O1—Ca1ii | 2.296 (4) |
| | | |
O5—Ca1—O1i | 99.20 (14) | O6—C7—O5 | 125.8 (5) |
O5—Ca1—O3 | 101.06 (13) | O6—C7—C8 | 116.8 (4) |
O1i—Ca1—O3 | 156.57 (14) | O5—C7—C8 | 117.4 (4) |
O5—Ca1—O2 | 92.13 (14) | C4—O4—Ca1ii | 127.4 (3) |
O1i—Ca1—O2 | 79.94 (13) | C4—O3—Ca1 | 140.3 (3) |
O3—Ca1—O2 | 87.64 (13) | O3—C4—O4 | 125.7 (5) |
O5—Ca1—O1W | 78.83 (14) | O3—C4—C5 | 117.6 (5) |
O1i—Ca1—O1W | 89.93 (14) | O4—C4—C5 | 116.8 (5) |
O3—Ca1—O1W | 105.43 (13) | N2—C5—C6 | 110.2 (4) |
O2—Ca1—O1W | 165.24 (13) | N2—C5—C4 | 108.3 (4) |
O5—Ca1—O4i | 161.98 (14) | C6—C5—C4 | 110.2 (4) |
O1i—Ca1—O4i | 84.41 (13) | N2—C5—H5A | 109.4 |
O3—Ca1—O4i | 79.97 (13) | C6—C5—H5A | 109.4 |
O2—Ca1—O4i | 105.90 (13) | C4—C5—H5A | 109.4 |
O1W—Ca1—O4i | 83.54 (13) | C5—C6—H6C | 109.5 |
O5—Ca1—H1W | 69.1 (12) | C5—C6—H6A | 109.5 |
O1i—Ca1—H1W | 79.1 (13) | H6C—C6—H6A | 109.5 |
O3—Ca1—H1W | 119.3 (12) | C5—C6—H6B | 109.5 |
O2—Ca1—H1W | 149.0 (10) | H6C—C6—H6B | 109.5 |
O1W—Ca1—H1W | 16.3 (10) | H6A—C6—H6B | 109.5 |
O4i—Ca1—H1W | 94.5 (12) | C5—N2—H5N | 106 (4) |
O5—Ca1—H2W | 92.9 (11) | C5—N2—H6N | 116 (4) |
O1i—Ca1—H2W | 81.6 (13) | H5N—N2—H6N | 111 (6) |
O3—Ca1—H2W | 108.9 (13) | C5—N2—H4N | 107 (4) |
O2—Ca1—H2W | 161.4 (12) | H5N—N2—H4N | 113 (5) |
O1W—Ca1—H2W | 15.3 (11) | H6N—N2—H4N | 104 (5) |
O4i—Ca1—H2W | 70.0 (11) | C2—N1—H2N | 111 (4) |
H1W—Ca1—H2W | 24.9 (17) | C2—N1—H3N | 117 (4) |
C7—O5—Ca1 | 163.4 (4) | H2N—N1—H3N | 98 (5) |
Ca1—O1W—H1W | 102 (5) | C2—N1—H1N | 114 (4) |
Ca1—O1W—H2W | 108 (5) | H2N—N1—H1N | 105 (5) |
H1W—O1W—H2W | 100 (6) | H3N—N1—H1N | 109 (5) |
C8—N3—H9N | 111 (4) | O1—C1—O2 | 125.5 (5) |
C8—N3—H7N | 111 (4) | O1—C1—C2 | 118.9 (5) |
H9N—N3—H7N | 111 (6) | O2—C1—C2 | 115.5 (5) |
C8—N3—H8N | 110 (4) | N1—C2—C1 | 108.7 (4) |
H9N—N3—H8N | 113 (5) | N1—C2—C3 | 108.9 (4) |
H7N—N3—H8N | 101 (5) | C1—C2—C3 | 110.5 (5) |
C8—C9—H9C | 109.5 | N1—C2—H2A | 109.6 |
C8—C9—H9A | 109.5 | C1—C2—H2A | 109.6 |
H9C—C9—H9A | 109.5 | C3—C2—H2A | 109.6 |
C8—C9—H9B | 109.5 | C2—C3—H3A | 109.5 |
H9C—C9—H9B | 109.5 | C2—C3—H3B | 109.5 |
H9A—C9—H9B | 109.5 | H3A—C3—H3B | 109.5 |
N3—C8—C9 | 109.8 (4) | C2—C3—H3C | 109.5 |
N3—C8—C7 | 109.4 (4) | H3A—C3—H3C | 109.5 |
C9—C8—C7 | 110.6 (5) | H3B—C3—H3C | 109.5 |
N3—C8—H8A | 109.0 | C1—O1—Ca1ii | 147.9 (3) |
C9—C8—H8A | 109.0 | C1—O2—Ca1 | 126.2 (3) |
C7—C8—H8A | 109.0 | | |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
Crystal data top
C15H41Ca2N5O13·4(I)·2(H2O) | Z = 4 |
Mr = 1123.32 | F(000) = 2168 |
Monoclinic, P21/c | Dx = 2.096 Mg m−3 |
a = 22.842 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.3609 (13) Å | µ = 3.85 mm−1 |
c = 18.807 (3) Å | T = 100 K |
β = 97.734 (3)° | Needle, colourless |
V = 3559.1 (10) Å3 | 0.18 × 0.06 × 0.05 mm |
Data collection top
Bruker APEX CCD diffractometer | 7339 independent reflections |
Radiation source: microsource | 5475 reflections with I > 2σ(I) |
Multilayer optics monochromator | Rint = 0.103 |
ω scans | θmax = 26.5°, θmin = 0.9° |
Absorption correction: multi-scan SADABS | h = −28→28 |
Tmin = 0.570, Tmax = 0.755 | k = −10→10 |
41724 measured reflections | l = −23→23 |
Refinement top
Refinement on F2 | 15 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.046 | H 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 reflections | Δρmax = 2.00 e Å−3 |
420 parameters | Δρmin = −1.46 e Å−3 |
Crystal data top
C15H41Ca2N5O13·4(I)·2(H2O) | V = 3559.1 (10) Å3 |
Mr = 1123.32 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 22.842 (4) Å | µ = 3.85 mm−1 |
b = 8.3609 (13) Å | T = 100 K |
c = 18.807 (3) Å | 0.18 × 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 = 0.755 | Rint = 0.103 |
41724 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.046 | 15 restraints |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 2.00 e Å−3 |
7339 reflections | Δρmin = −1.46 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
I1 | 0.56851 (2) | 0.72857 (5) | 0.65183 (2) | 0.01631 (12) | |
I2 | 0.57243 (2) | 0.67891 (5) | 0.90174 (2) | 0.01641 (12) | |
I3 | 0.94569 (2) | 0.78083 (6) | 0.84436 (2) | 0.01830 (12) | |
I4 | 0.92274 (2) | 0.70133 (6) | 0.60187 (3) | 0.02210 (12) | |
Ca1 | 0.74407 (5) | 0.18112 (15) | 0.87017 (7) | 0.0102 (3) | |
Ca2 | 0.74623 (5) | 0.14511 (16) | 0.62740 (7) | 0.0112 (3) | |
O1 | 0.65489 (18) | 0.1027 (5) | 0.6691 (2) | 0.0155 (10) | |
O2 | 0.67798 (18) | 0.0319 (5) | 0.7843 (2) | 0.0114 (10) | |
C1 | 0.6428 (3) | 0.0827 (7) | 0.7322 (3) | 0.0092 (13) | |
C21 | 0.5805 (3) | 0.1316 (8) | 0.7443 (3) | 0.0123 (14) | |
H21 | 0.5515 | 0.0845 | 0.7054 | 0.015* | |
C31 | 0.5728 (3) | 0.3104 (8) | 0.7442 (4) | 0.0176 (15) | |
H31A | 0.6015 | 0.3578 | 0.7817 | 0.026* | |
H31B | 0.5327 | 0.3365 | 0.7536 | 0.026* | |
H31C | 0.5790 | 0.3534 | 0.6974 | 0.026* | |
N1 | 0.5690 (2) | 0.0647 (7) | 0.8150 (3) | 0.0144 (12) | |
H1A | 0.5342 (17) | 0.101 (8) | 0.828 (3) | 0.017* | |
H1B | 0.597 (2) | 0.109 (7) | 0.849 (3) | 0.017* | |
H1C | 0.567 (3) | −0.042 (3) | 0.806 (4) | 0.017* | |
O3 | 0.7303 (2) | 0.4169 (5) | 0.6533 (3) | 0.0193 (11) | |
O4 | 0.7239 (2) | 0.3555 (5) | 0.7678 (2) | 0.0171 (11) | |
C4 | 0.7256 (3) | 0.4535 (8) | 0.7174 (4) | 0.0120 (14) | |
C51 | 0.7267 (3) | 0.6332 (8) | 0.7358 (3) | 0.0128 (14) | |
H51 | 0.7082 | 0.6957 | 0.6933 | 0.015* | |
C6 | 0.7906 (3) | 0.6847 (8) | 0.7556 (4) | 0.0178 (15) | |
H6A | 0.8091 | 0.6196 | 0.7958 | 0.027* | |
H6B | 0.7919 | 0.7976 | 0.7696 | 0.027* | |
H6C | 0.8119 | 0.6700 | 0.7142 | 0.027* | |
N2 | 0.6932 (2) | 0.6602 (7) | 0.7979 (3) | 0.0157 (13) | |
H2A | 0.702 (3) | 0.589 (7) | 0.835 (3) | 0.024* | |
H2B | 0.6532 (11) | 0.652 (8) | 0.781 (3) | 0.024* | |
H2C | 0.701 (3) | 0.757 (5) | 0.822 (3) | 0.024* | |
O5 | 0.81341 (19) | 0.0801 (5) | 0.7249 (2) | 0.0150 (10) | |
O6 | 0.83890 (19) | 0.1560 (6) | 0.8381 (2) | 0.0208 (11) | |
C7 | 0.8493 (3) | 0.1333 (8) | 0.7746 (3) | 0.0137 (14) | |
C8 | 0.9106 (3) | 0.1805 (8) | 0.7590 (4) | 0.0180 (16) | |
H8 | 0.9405 | 0.1496 | 0.8006 | 0.022* | |
C9 | 0.9122 (4) | 0.3603 (9) | 0.7485 (5) | 0.033 (2) | |
H9A | 0.8856 | 0.3897 | 0.7051 | 0.050* | |
H9B | 0.9526 | 0.3936 | 0.7434 | 0.050* | |
H9C | 0.8995 | 0.4139 | 0.7902 | 0.050* | |
N3 | 0.9235 (2) | 0.0956 (7) | 0.6937 (3) | 0.0158 (13) | |
H3A | 0.899 (2) | 0.119 (8) | 0.653 (2) | 0.019* | |
H3B | 0.919 (3) | −0.013 (3) | 0.700 (4) | 0.019* | |
H3C | 0.9596 (16) | 0.109 (8) | 0.678 (3) | 0.019* | |
O7 | 0.80765 (19) | 0.3368 (5) | 0.4822 (2) | 0.0158 (10) | |
O8 | 0.83607 (18) | 0.1996 (5) | 0.5826 (2) | 0.0147 (10) | |
C10 | 0.6444 (3) | 0.2134 (8) | 0.4760 (4) | 0.0129 (14) | |
C11 | 0.5822 (3) | 0.2203 (8) | 0.4946 (3) | 0.0118 (14) | |
H11 | 0.5538 | 0.2041 | 0.4499 | 0.014* | |
C12 | 0.5705 (3) | 0.3822 (9) | 0.5265 (4) | 0.0213 (17) | |
H12A | 0.5979 | 0.3987 | 0.5707 | 0.032* | |
H12B | 0.5298 | 0.3857 | 0.5376 | 0.032* | |
H12C | 0.5762 | 0.4666 | 0.4920 | 0.032* | |
N4 | 0.5729 (2) | 0.0928 (7) | 0.5467 (3) | 0.0139 (12) | |
H4A | 0.576 (3) | −0.009 (4) | 0.530 (3) | 0.017* | |
H4B | 0.5378 (17) | 0.097 (8) | 0.566 (3) | 0.017* | |
H4C | 0.599 (2) | 0.104 (8) | 0.588 (2) | 0.017* | |
O9 | 0.65355 (19) | 0.2840 (5) | 0.4195 (2) | 0.0155 (10) | |
O10 | 0.68299 (18) | 0.1427 (5) | 0.5188 (2) | 0.0130 (10) | |
C13 | 0.8450 (3) | 0.2738 (8) | 0.5270 (4) | 0.0125 (14) | |
C14 | 0.9102 (3) | 0.2781 (7) | 0.5145 (3) | 0.0116 (14) | |
H14 | 0.9355 | 0.3030 | 0.5608 | 0.014* | |
C15 | 0.9296 (3) | 0.1189 (8) | 0.4858 (4) | 0.0249 (18) | |
H15A | 0.9716 | 0.1241 | 0.4803 | 0.037* | |
H15B | 0.9064 | 0.0971 | 0.4390 | 0.037* | |
H15C | 0.9232 | 0.0332 | 0.5194 | 0.037* | |
N5 | 0.9182 (2) | 0.4066 (7) | 0.4607 (3) | 0.0149 (13) | |
H5A | 0.9559 (14) | 0.395 (8) | 0.450 (3) | 0.018* | |
H5B | 0.917 (3) | 0.506 (4) | 0.481 (3) | 0.018* | |
H5C | 0.894 (2) | 0.385 (8) | 0.419 (2) | 0.018* | |
O1W | 0.8337 (2) | 0.7023 (6) | 0.9426 (2) | 0.0208 (11) | |
H1W | 0.8639 | 0.7234 | 0.9162 | 0.025* | |
H2W | 0.8573 | 0.7277 | 0.9847 | 0.025* | |
O2W | 0.6958 (2) | −0.3676 (6) | 0.5441 (2) | 0.0203 (11) | |
H4W | 0.7073 | −0.4394 | 0.5805 | 0.024* | |
H3W | 0.6567 | −0.3325 | 0.5462 | 0.024* | |
O3W | 0.7674 (2) | −0.1157 (5) | 0.5881 (2) | 0.0208 (11) | |
H5W | 0.7430 | −0.2002 | 0.5734 | 0.025* | |
H6W | 0.8046 | −0.1595 | 0.5914 | 0.025* | |
O4W | 0.7501 (2) | 0.4650 (5) | 0.9161 (2) | 0.0183 (11) | |
H7W | 0.7780 | 0.5446 | 0.9252 | 0.022* | |
H8W | 0.7279 | 0.4294 | 0.9506 | 0.022* | |
O5W | 0.73759 (18) | −0.0974 (5) | 0.9098 (2) | 0.0140 (10) | |
H9W | 0.7695 | −0.1643 | 0.9204 | 0.017* | |
H10W | 0.7237 | −0.1092 | 0.9532 | 0.017* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0147 (2) | 0.0159 (2) | 0.0186 (3) | −0.00246 (18) | 0.00305 (18) | 0.00132 (19) |
I2 | 0.0167 (2) | 0.0167 (2) | 0.0171 (3) | 0.00184 (18) | 0.00670 (18) | 0.00420 (19) |
I3 | 0.0135 (2) | 0.0228 (3) | 0.0193 (3) | 0.00161 (18) | 0.00484 (18) | −0.0049 (2) |
I4 | 0.0335 (3) | 0.0172 (3) | 0.0154 (3) | 0.0019 (2) | 0.0026 (2) | −0.0007 (2) |
Ca1 | 0.0107 (6) | 0.0129 (7) | 0.0071 (7) | −0.0020 (5) | 0.0013 (5) | 0.0000 (5) |
Ca2 | 0.0123 (7) | 0.0135 (7) | 0.0083 (7) | 0.0016 (5) | 0.0025 (5) | −0.0008 (5) |
O1 | 0.011 (2) | 0.024 (3) | 0.011 (3) | −0.0035 (19) | 0.0008 (19) | −0.002 (2) |
O2 | 0.010 (2) | 0.012 (2) | 0.012 (2) | −0.0007 (18) | −0.0013 (18) | 0.0014 (19) |
C1 | 0.014 (3) | 0.006 (3) | 0.008 (3) | −0.005 (2) | 0.004 (3) | −0.004 (2) |
C21 | 0.014 (3) | 0.018 (4) | 0.005 (3) | 0.001 (3) | 0.003 (3) | 0.000 (3) |
C31 | 0.019 (4) | 0.021 (4) | 0.014 (4) | 0.005 (3) | 0.008 (3) | 0.001 (3) |
N1 | 0.010 (3) | 0.017 (3) | 0.016 (3) | −0.003 (2) | 0.005 (2) | −0.002 (3) |
O3 | 0.024 (3) | 0.018 (3) | 0.018 (3) | 0.002 (2) | 0.010 (2) | 0.000 (2) |
O4 | 0.023 (3) | 0.013 (3) | 0.015 (3) | 0.002 (2) | 0.002 (2) | 0.001 (2) |
C4 | 0.010 (3) | 0.011 (3) | 0.015 (4) | 0.001 (3) | 0.004 (3) | −0.003 (3) |
C51 | 0.019 (4) | 0.012 (3) | 0.007 (3) | 0.002 (3) | 0.003 (3) | 0.003 (3) |
C6 | 0.012 (3) | 0.019 (4) | 0.023 (4) | −0.001 (3) | 0.004 (3) | −0.004 (3) |
N2 | 0.015 (3) | 0.018 (3) | 0.015 (3) | −0.002 (3) | 0.003 (2) | −0.005 (2) |
O5 | 0.014 (2) | 0.022 (3) | 0.008 (2) | −0.003 (2) | 0.0003 (19) | 0.003 (2) |
O6 | 0.016 (3) | 0.037 (3) | 0.010 (3) | 0.001 (2) | 0.003 (2) | −0.001 (2) |
C7 | 0.010 (3) | 0.021 (4) | 0.011 (4) | 0.003 (3) | 0.005 (3) | 0.000 (3) |
C8 | 0.013 (3) | 0.026 (4) | 0.015 (4) | −0.002 (3) | 0.002 (3) | −0.006 (3) |
C9 | 0.036 (5) | 0.025 (5) | 0.040 (5) | −0.006 (4) | 0.014 (4) | −0.005 (4) |
N3 | 0.010 (3) | 0.021 (3) | 0.017 (3) | −0.003 (3) | 0.005 (2) | 0.000 (3) |
O7 | 0.013 (2) | 0.022 (3) | 0.011 (3) | 0.003 (2) | −0.0014 (19) | 0.000 (2) |
O8 | 0.013 (2) | 0.019 (3) | 0.013 (3) | 0.0019 (19) | 0.0033 (19) | 0.002 (2) |
C10 | 0.013 (3) | 0.012 (3) | 0.014 (4) | −0.002 (3) | 0.005 (3) | −0.003 (3) |
C11 | 0.009 (3) | 0.018 (4) | 0.008 (3) | 0.002 (3) | 0.002 (3) | 0.003 (3) |
C12 | 0.016 (4) | 0.025 (4) | 0.025 (4) | 0.004 (3) | 0.009 (3) | −0.001 (3) |
N4 | 0.010 (3) | 0.018 (3) | 0.014 (3) | 0.000 (2) | 0.003 (2) | 0.001 (3) |
O9 | 0.017 (2) | 0.018 (3) | 0.012 (3) | 0.002 (2) | 0.0053 (19) | 0.004 (2) |
O10 | 0.011 (2) | 0.018 (3) | 0.010 (2) | 0.0033 (19) | −0.0008 (18) | 0.0026 (19) |
C13 | 0.014 (3) | 0.009 (3) | 0.014 (4) | 0.000 (3) | 0.001 (3) | −0.006 (3) |
C14 | 0.011 (3) | 0.013 (3) | 0.009 (4) | −0.003 (3) | −0.004 (3) | 0.000 (3) |
C15 | 0.026 (4) | 0.018 (4) | 0.034 (5) | 0.004 (3) | 0.017 (3) | 0.002 (3) |
N5 | 0.012 (3) | 0.017 (3) | 0.015 (3) | −0.005 (3) | −0.001 (2) | −0.001 (3) |
O1W | 0.019 (3) | 0.029 (3) | 0.015 (3) | −0.004 (2) | 0.003 (2) | −0.001 (2) |
O2W | 0.016 (3) | 0.026 (3) | 0.019 (3) | −0.001 (2) | 0.004 (2) | 0.003 (2) |
O3W | 0.022 (3) | 0.016 (3) | 0.024 (3) | −0.002 (2) | 0.001 (2) | −0.003 (2) |
O4W | 0.022 (3) | 0.016 (3) | 0.018 (3) | −0.009 (2) | 0.005 (2) | −0.001 (2) |
O5W | 0.019 (2) | 0.017 (3) | 0.007 (2) | 0.0035 (19) | 0.0017 (19) | 0.0032 (19) |
Geometric parameters (Å, º) top
Ca1—O6 | 2.335 (5) | C8—N3 | 1.482 (9) |
Ca1—O9i | 2.395 (5) | C8—C9 | 1.518 (10) |
Ca1—O7i | 2.398 (4) | C8—H8 | 1.0000 |
Ca1—O2 | 2.405 (4) | C9—H9A | 0.9800 |
Ca1—O4 | 2.410 (5) | C9—H9B | 0.9800 |
Ca1—O5W | 2.456 (4) | C9—H9C | 0.9800 |
Ca1—O4W | 2.523 (5) | N3—H3A | 0.92 (2) |
Ca1—C7 | 3.214 (6) | N3—H3B | 0.92 (2) |
Ca1—H8W | 2.6233 | N3—H3C | 0.92 (2) |
Ca2—O5 | 2.292 (4) | O7—C13 | 1.233 (7) |
Ca2—O10 | 2.338 (4) | O8—C13 | 1.255 (8) |
Ca2—O1 | 2.353 (4) | C10—O10 | 1.258 (7) |
Ca2—O3 | 2.362 (5) | C10—O9 | 1.258 (8) |
Ca2—O8 | 2.365 (4) | C10—C11 | 1.509 (8) |
Ca2—O3W | 2.373 (5) | C11—N4 | 1.482 (8) |
Ca2—C4 | 3.155 (6) | C11—C12 | 1.519 (9) |
O1—C1 | 1.264 (7) | C11—H11 | 1.0000 |
O2—C1 | 1.255 (7) | C12—H12A | 0.9800 |
C1—C21 | 1.528 (8) | C12—H12B | 0.9800 |
C21—N1 | 1.498 (8) | C12—H12C | 0.9800 |
C21—C31 | 1.506 (9) | N4—H4A | 0.91 (2) |
C21—H21 | 1.0000 | N4—H4B | 0.92 (2) |
C31—H31A | 0.9800 | N4—H4C | 0.92 (2) |
C31—H31B | 0.9800 | C13—C14 | 1.541 (9) |
C31—H31C | 0.9800 | C14—N5 | 1.503 (8) |
N1—H1A | 0.92 (2) | C14—C15 | 1.525 (9) |
N1—H1B | 0.92 (2) | C14—H14 | 1.0000 |
N1—H1C | 0.91 (2) | C15—H15A | 0.9800 |
O3—C4 | 1.264 (8) | C15—H15B | 0.9800 |
O4—C4 | 1.257 (8) | C15—H15C | 0.9800 |
C4—C51 | 1.541 (9) | N5—H5A | 0.91 (2) |
C51—N2 | 1.498 (8) | N5—H5B | 0.92 (2) |
C51—C6 | 1.518 (9) | N5—H5C | 0.91 (2) |
C51—H51 | 1.0000 | O1W—H1W | 0.9200 |
C6—H6A | 0.9800 | O1W—H2W | 0.9200 |
C6—H6B | 0.9800 | O2W—H4W | 0.9222 |
C6—H6C | 0.9800 | O2W—H3W | 0.9464 |
N2—H2A | 0.92 (2) | O3W—H5W | 0.9200 |
N2—H2B | 0.93 (2) | O3W—H6W | 0.9200 |
N2—H2C | 0.93 (2) | O4W—H7W | 0.9206 |
O5—C7 | 1.239 (7) | O4W—H8W | 0.9255 |
O6—C7 | 1.263 (8) | O5W—H9W | 0.9200 |
C7—C8 | 1.522 (9) | O5W—H10W | 0.9200 |
| | | |
O6—Ca1—O9i | 172.01 (16) | C51—C6—H6B | 109.5 |
O6—Ca1—O7i | 75.43 (16) | H6A—C6—H6B | 109.5 |
O9i—Ca1—O7i | 96.88 (16) | C51—C6—H6C | 109.5 |
O6—Ca1—O2 | 107.47 (16) | H6A—C6—H6C | 109.5 |
O9i—Ca1—O2 | 79.99 (15) | H6B—C6—H6C | 109.5 |
O7i—Ca1—O2 | 143.97 (16) | C51—N2—H2A | 115 (4) |
O6—Ca1—O4 | 86.12 (16) | C51—N2—H2B | 107 (4) |
O9i—Ca1—O4 | 98.81 (16) | H2A—N2—H2B | 108 (6) |
O7i—Ca1—O4 | 140.20 (16) | C51—N2—H2C | 116 (5) |
O2—Ca1—O4 | 75.05 (15) | H2A—N2—H2C | 100 (6) |
O6—Ca1—O5W | 95.11 (17) | H2B—N2—H2C | 110 (6) |
O9i—Ca1—O5W | 84.69 (15) | C7—O5—Ca2 | 145.2 (5) |
O7i—Ca1—O5W | 74.23 (15) | C7—O6—Ca1 | 123.8 (4) |
O2—Ca1—O5W | 69.74 (14) | O5—C7—O6 | 125.3 (6) |
O4—Ca1—O5W | 143.44 (15) | O5—C7—C8 | 118.7 (6) |
O6—Ca1—O4W | 99.37 (17) | O6—C7—C8 | 115.9 (6) |
O9i—Ca1—O4W | 76.33 (15) | O5—C7—Ca1 | 89.9 (4) |
O7i—Ca1—O4W | 76.07 (15) | C8—C7—Ca1 | 148.4 (4) |
O2—Ca1—O4W | 135.90 (15) | N3—C8—C9 | 110.8 (6) |
O4—Ca1—O4W | 72.54 (15) | N3—C8—C7 | 109.0 (5) |
O5W—Ca1—O4W | 142.30 (15) | C9—C8—C7 | 108.7 (6) |
O6—Ca1—C7 | 19.06 (16) | N3—C8—H8 | 109.4 |
O9i—Ca1—C7 | 168.84 (16) | C9—C8—H8 | 109.4 |
O7i—Ca1—C7 | 94.24 (16) | C7—C8—H8 | 109.4 |
O2—Ca1—C7 | 90.51 (16) | C8—C9—H9A | 109.5 |
O4—Ca1—C7 | 72.87 (16) | C8—C9—H9B | 109.5 |
O5W—Ca1—C7 | 97.58 (16) | H9A—C9—H9B | 109.5 |
O4W—Ca1—C7 | 107.32 (17) | C8—C9—H9C | 109.5 |
O6—Ca1—H8W | 115.3 | H9A—C9—H9C | 109.5 |
O9i—Ca1—H8W | 59.0 | H9B—C9—H9C | 109.5 |
O7i—Ca1—H8W | 70.0 | C8—N3—H3A | 115 (4) |
O2—Ca1—H8W | 132.3 | C8—N3—H3B | 109 (4) |
O4—Ca1—H8W | 87.4 | H3A—N3—H3B | 104 (6) |
O5W—Ca1—H8W | 123.8 | C8—N3—H3C | 119 (4) |
O4W—Ca1—H8W | 20.6 | H3A—N3—H3C | 101 (6) |
C7—Ca1—H8W | 126.5 | H3B—N3—H3C | 106 (6) |
O5—Ca2—O10 | 164.83 (17) | C13—O7—Ca1ii | 148.8 (4) |
O5—Ca2—O1 | 103.04 (16) | C13—O8—Ca2 | 129.6 (4) |
O10—Ca2—O1 | 79.57 (15) | O10—C10—O9 | 125.4 (6) |
O5—Ca2—O3 | 99.71 (17) | O10—C10—C11 | 118.0 (6) |
O10—Ca2—O3 | 95.40 (16) | O9—C10—C11 | 116.5 (6) |
O1—Ca2—O3 | 84.73 (16) | N4—C11—C10 | 110.4 (5) |
O5—Ca2—O8 | 79.11 (16) | N4—C11—C12 | 109.4 (5) |
O10—Ca2—O8 | 98.86 (16) | C10—C11—C12 | 110.3 (5) |
O1—Ca2—O8 | 177.13 (17) | N4—C11—H11 | 108.9 |
O3—Ca2—O8 | 93.06 (16) | C10—C11—H11 | 108.9 |
O5—Ca2—O3W | 83.61 (16) | C12—C11—H11 | 108.9 |
O10—Ca2—O3W | 81.23 (16) | C11—C12—H12A | 109.5 |
O1—Ca2—O3W | 101.09 (17) | C11—C12—H12B | 109.5 |
O3—Ca2—O3W | 172.56 (17) | H12A—C12—H12B | 109.5 |
O8—Ca2—O3W | 80.97 (16) | C11—C12—H12C | 109.5 |
O5—Ca2—C4 | 84.09 (17) | H12A—C12—H12C | 109.5 |
O10—Ca2—C4 | 110.90 (16) | H12B—C12—H12C | 109.5 |
O1—Ca2—C4 | 74.96 (16) | C11—N4—H4A | 114 (4) |
O3—Ca2—C4 | 20.77 (16) | C11—N4—H4B | 116 (4) |
O8—Ca2—C4 | 103.51 (17) | H4A—N4—H4B | 107 (6) |
O3W—Ca2—C4 | 165.84 (17) | C11—N4—H4C | 111 (4) |
C1—O1—Ca2 | 130.4 (4) | H4A—N4—H4C | 108 (6) |
C1—O2—Ca1 | 128.8 (4) | H4B—N4—H4C | 100 (6) |
O2—C1—O1 | 125.5 (6) | C10—O9—Ca1ii | 129.4 (4) |
O2—C1—C21 | 119.0 (5) | C10—O10—Ca2 | 148.4 (4) |
O1—C1—C21 | 115.5 (5) | O7—C13—O8 | 127.3 (6) |
N1—C21—C31 | 109.7 (5) | O7—C13—C14 | 118.7 (6) |
N1—C21—C1 | 108.2 (5) | O8—C13—C14 | 114.0 (5) |
C31—C21—C1 | 112.2 (5) | N5—C14—C15 | 108.5 (5) |
N1—C21—H21 | 108.9 | N5—C14—C13 | 109.1 (5) |
C31—C21—H21 | 108.9 | C15—C14—C13 | 111.5 (5) |
C1—C21—H21 | 108.9 | N5—C14—H14 | 109.2 |
C21—C31—H31A | 109.5 | C15—C14—H14 | 109.2 |
C21—C31—H31B | 109.5 | C13—C14—H14 | 109.2 |
H31A—C31—H31B | 109.5 | C14—C15—H15A | 109.5 |
C21—C31—H31C | 109.5 | C14—C15—H15B | 109.5 |
H31A—C31—H31C | 109.5 | H15A—C15—H15B | 109.5 |
H31B—C31—H31C | 109.5 | C14—C15—H15C | 109.5 |
C21—N1—H1A | 113 (4) | H15A—C15—H15C | 109.5 |
C21—N1—H1B | 107 (4) | H15B—C15—H15C | 109.5 |
H1A—N1—H1B | 103 (6) | C14—N5—H5A | 106 (4) |
C21—N1—H1C | 102 (4) | C14—N5—H5B | 111 (4) |
H1A—N1—H1C | 111 (6) | H5A—N5—H5B | 106 (6) |
H1B—N1—H1C | 123 (6) | C14—N5—H5C | 108 (4) |
C4—O3—Ca2 | 117.7 (4) | H5A—N5—H5C | 106 (6) |
C4—O4—Ca1 | 167.0 (4) | H5B—N5—H5C | 119 (6) |
O4—C4—O3 | 125.2 (6) | H1W—O1W—H2W | 91.4 |
O4—C4—C51 | 117.9 (6) | H4W—O2W—H3W | 110.3 |
O3—C4—C51 | 116.7 (6) | Ca2—O3W—H5W | 131.3 |
O4—C4—Ca2 | 83.9 (4) | Ca2—O3W—H6W | 124.8 |
C51—C4—Ca2 | 156.6 (4) | H5W—O3W—H6W | 103.4 |
N2—C51—C6 | 110.0 (5) | Ca1—O4W—H7W | 138.5 |
N2—C51—C4 | 109.1 (5) | Ca1—O4W—H8W | 85.8 |
C6—C51—C4 | 108.6 (5) | H7W—O4W—H8W | 122.2 |
N2—C51—H51 | 109.7 | Ca1—O5W—H9W | 124.3 |
C6—C51—H51 | 109.7 | Ca1—O5W—H10W | 114.3 |
C4—C51—H51 | 109.7 | H9W—O5W—H10W | 95.7 |
C51—C6—H6A | 109.5 | | |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2. |
Crystal data top
C6H18MnN2O6·2(Cl)·2(H2O) | Z = 2 |
Mr = 376.09 | F(000) = 390 |
Monoclinic, P21/c | Dx = 1.567 Mg m−3 |
a = 4.7294 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 19.101 (4) Å | µ = 1.19 mm−1 |
c = 9.0705 (17) Å | T = 100 K |
β = 103.395 (3)° | Needle, colourless |
V = 797.1 (3) Å3 | 0.40 × 0.07 × 0.07 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 1637 independent reflections |
Radiation source: microsource | 1419 reflections with I > 2σ(I) |
Multilayer optics monochromator | Rint = 0.069 |
ω scans | θmax = 26.5°, θmin = 2.5° |
Absorption correction: multi-scan SADABS | h = −5→5 |
Tmin = 0.565, Tmax = 0.745 | k = −23→23 |
9455 measured reflections | l = −11→11 |
Refinement top
Refinement on F2 | 5 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.030 | H 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 reflections | Δρmax = 0.41 e Å−3 |
110 parameters | Δρmin = −0.28 e Å−3 |
Crystal data top
C6H18MnN2O6·2(Cl)·2(H2O) | V = 797.1 (3) Å3 |
Mr = 376.09 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 4.7294 (9) Å | µ = 1.19 mm−1 |
b = 19.101 (4) Å | T = 100 K |
c = 9.0705 (17) Å | 0.40 × 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 = 0.745 | Rint = 0.069 |
9455 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.030 | 5 restraints |
wR(F2) = 0.074 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.41 e Å−3 |
1637 reflections | Δρmin = −0.28 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl1 | 1.14813 (11) | 0.74272 (3) | 0.51100 (5) | 0.01587 (15) | |
Mn2 | 0.5000 | 0.5000 | 0.5000 | 0.00991 (14) | |
O1 | 0.8297 (3) | 0.57126 (7) | 0.46174 (15) | 0.0121 (3) | |
O2 | 1.1996 (3) | 0.56861 (7) | 0.34688 (15) | 0.0129 (3) | |
C1 | 0.9515 (4) | 0.58773 (10) | 0.3584 (2) | 0.0107 (4) | |
C2 | 0.7897 (4) | 0.63498 (10) | 0.2301 (2) | 0.0130 (4) | |
H2 | 0.9310 | 0.6685 | 0.2022 | 0.016* | |
C3 | 0.6497 (5) | 0.59220 (12) | 0.0918 (2) | 0.0214 (5) | |
H3A | 0.5091 | 0.5596 | 0.1179 | 0.032* | |
H3B | 0.7998 | 0.5658 | 0.0571 | 0.032* | |
H3C | 0.5497 | 0.6236 | 0.0108 | 0.032* | |
N1 | 0.5649 (4) | 0.67528 (9) | 0.28562 (19) | 0.0124 (4) | |
H1A | 0.455 (4) | 0.7014 (10) | 0.206 (2) | 0.015* | |
H1B | 0.657 (5) | 0.7030 (10) | 0.369 (2) | 0.015* | |
H1C | 0.432 (4) | 0.6477 (10) | 0.319 (2) | 0.015* | |
O1W | 0.4853 (3) | 0.56036 (8) | 0.70187 (17) | 0.0162 (3) | |
H3D | 0.344 (4) | 0.5809 (11) | 0.715 (3) | 0.019* | |
H3E | 0.631 (4) | 0.5837 (11) | 0.728 (3) | 0.019* | |
O2W | 0.9933 (4) | 0.63929 (8) | 0.76154 (17) | 0.0200 (4) | |
H4B | 1.042 (5) | 0.6679 (11) | 0.836 (2) | 0.024* | |
H4A | 0.995 (5) | 0.6641 (11) | 0.685 (2) | 0.024* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0181 (3) | 0.0150 (3) | 0.0133 (3) | −0.0032 (2) | 0.0011 (2) | −0.00158 (19) |
Mn2 | 0.0095 (3) | 0.0104 (2) | 0.0098 (2) | 0.00046 (16) | 0.00209 (18) | 0.00158 (16) |
O1 | 0.0110 (7) | 0.0136 (7) | 0.0116 (7) | −0.0014 (6) | 0.0028 (6) | 0.0012 (6) |
O2 | 0.0113 (8) | 0.0142 (7) | 0.0135 (7) | 0.0018 (6) | 0.0037 (6) | 0.0030 (6) |
C1 | 0.0104 (11) | 0.0097 (9) | 0.0110 (10) | −0.0026 (8) | 0.0001 (8) | −0.0032 (8) |
C2 | 0.0115 (11) | 0.0146 (10) | 0.0129 (10) | 0.0020 (8) | 0.0029 (8) | 0.0014 (8) |
C3 | 0.0245 (13) | 0.0257 (12) | 0.0120 (11) | 0.0058 (10) | 0.0004 (9) | −0.0011 (9) |
N1 | 0.0113 (9) | 0.0129 (9) | 0.0126 (9) | 0.0013 (7) | 0.0020 (7) | 0.0029 (7) |
O1W | 0.0135 (8) | 0.0176 (8) | 0.0176 (8) | −0.0001 (6) | 0.0040 (7) | −0.0051 (6) |
O2W | 0.0237 (9) | 0.0215 (8) | 0.0143 (8) | −0.0036 (7) | 0.0033 (7) | −0.0023 (6) |
Geometric parameters (Å, º) top
Mn2—O1i | 2.1577 (14) | C2—H2 | 1.0000 |
Mn2—O1 | 2.1577 (14) | C3—H3A | 0.9800 |
Mn2—O1Wi | 2.1785 (15) | C3—H3B | 0.9800 |
Mn2—O1W | 2.1785 (15) | C3—H3C | 0.9800 |
Mn2—O2ii | 2.1795 (14) | N1—H1A | 0.930 (15) |
Mn2—O2iii | 2.1795 (14) | N1—H1B | 0.946 (15) |
O1—C1 | 1.249 (2) | N1—H1C | 0.922 (15) |
O2—C1 | 1.256 (2) | O1W—H3D | 0.808 (17) |
O2—Mn2iv | 2.1795 (14) | O1W—H3E | 0.810 (18) |
C1—C2 | 1.530 (3) | O2W—H4B | 0.856 (18) |
C2—N1 | 1.492 (3) | O2W—H4A | 0.839 (18) |
C2—C3 | 1.515 (3) | | |
| | | |
O1i—Mn2—O1 | 180.00 (5) | N1—C2—C1 | 108.53 (16) |
O1i—Mn2—O1Wi | 88.07 (5) | C3—C2—C1 | 110.94 (16) |
O1—Mn2—O1Wi | 91.93 (5) | N1—C2—H2 | 109.0 |
O1i—Mn2—O1W | 91.93 (5) | C3—C2—H2 | 109.0 |
O1—Mn2—O1W | 88.07 (5) | C1—C2—H2 | 109.0 |
O1Wi—Mn2—O1W | 180.0 | C2—C3—H3A | 109.5 |
O1i—Mn2—O2ii | 95.35 (5) | C2—C3—H3B | 109.5 |
O1—Mn2—O2ii | 84.65 (5) | H3A—C3—H3B | 109.5 |
O1Wi—Mn2—O2ii | 85.74 (5) | C2—C3—H3C | 109.5 |
O1W—Mn2—O2ii | 94.26 (5) | H3A—C3—H3C | 109.5 |
O1i—Mn2—O2iii | 84.65 (5) | H3B—C3—H3C | 109.5 |
O1—Mn2—O2iii | 95.35 (5) | C2—N1—H1A | 109.2 (14) |
O1Wi—Mn2—O2iii | 94.26 (5) | C2—N1—H1B | 109.0 (14) |
O1W—Mn2—O2iii | 85.74 (5) | H1A—N1—H1B | 113.1 (18) |
O2ii—Mn2—O2iii | 180.0 | C2—N1—H1C | 114.1 (13) |
C1—O1—Mn2 | 139.10 (12) | H1A—N1—H1C | 105.0 (19) |
C1—O2—Mn2iv | 127.23 (13) | H1B—N1—H1C | 106 (2) |
O1—C1—O2 | 126.27 (18) | Mn2—O1W—H3D | 125.0 (17) |
O1—C1—C2 | 118.88 (18) | Mn2—O1W—H3E | 110.0 (17) |
O2—C1—C2 | 114.84 (17) | H3D—O1W—H3E | 112 (2) |
N1—C2—C3 | 110.42 (17) | H4B—O2W—H4A | 103 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iii) −x+2, −y+1, −z+1; (iv) x+1, y, z. |
Crystal data top
C6H18MnN2O6·2(Br)·2(H2O) | Z = 2 |
Mr = 465.01 | F(000) = 462 |
Monoclinic, P21/c | Dx = 1.846 Mg m−3 |
a = 4.7592 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 19.571 (2) Å | µ = 5.59 mm−1 |
c = 9.1998 (11) Å | T = 100 K |
β = 102.450 (2)° | Needle, colourless |
V = 836.72 (18) Å3 | 0.30 × 0.07 × 0.07 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 2500 independent reflections |
Radiation source: microsource | 2207 reflections with I > 2σ(I) |
Multilayer optics monochromator | Rint = 0.043 |
ω scans | θmax = 30.8°, θmin = 2.5° |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | h = −6→6 |
Tmin = 0.507, Tmax = 0.746 | k = −27→27 |
12568 measured reflections | l = −13→13 |
Refinement top
Refinement on F2 | 5 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.029 | H 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 reflections | Δρmax = 0.83 e Å−3 |
110 parameters | Δρmin = −0.43 e Å−3 |
Crystal data top
C6H18MnN2O6·2(Br)·2(H2O) | V = 836.72 (18) Å3 |
Mr = 465.01 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 4.7592 (6) Å | µ = 5.59 mm−1 |
b = 19.571 (2) Å | T = 100 K |
c = 9.1998 (11) Å | 0.30 × 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 = 0.746 | Rint = 0.043 |
12568 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.029 | 5 restraints |
wR(F2) = 0.062 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.83 e Å−3 |
2500 reflections | Δρmin = −0.43 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Br1 | 1.15542 (5) | 0.74336 (2) | 0.50714 (2) | 0.01593 (7) | |
Mn1 | 0.5000 | 0.5000 | 0.5000 | 0.00944 (10) | |
O1 | 0.8292 (3) | 0.56913 (7) | 0.46041 (16) | 0.0115 (3) | |
O2 | 1.2030 (3) | 0.56632 (7) | 0.34946 (16) | 0.0126 (3) | |
C1 | 0.9536 (4) | 0.58471 (10) | 0.3589 (2) | 0.0107 (4) | |
C2 | 0.7976 (4) | 0.63027 (11) | 0.2311 (2) | 0.0133 (4) | |
H2 | 0.9384 | 0.6632 | 0.2038 | 0.016* | |
C3 | 0.6662 (5) | 0.58766 (12) | 0.0954 (2) | 0.0208 (5) | |
H3A | 0.5347 | 0.5538 | 0.1226 | 0.031* | |
H3B | 0.8194 | 0.5642 | 0.0590 | 0.031* | |
H3C | 0.5597 | 0.6175 | 0.0170 | 0.031* | |
N1 | 0.5703 (4) | 0.66897 (9) | 0.2837 (2) | 0.0126 (3) | |
H1A | 0.475 (5) | 0.6959 (11) | 0.212 (2) | 0.015* | |
H1B | 0.651 (5) | 0.6954 (11) | 0.361 (2) | 0.015* | |
H1C | 0.445 (5) | 0.6410 (11) | 0.312 (3) | 0.015* | |
O1W | 0.4823 (3) | 0.55852 (8) | 0.69944 (18) | 0.0166 (3) | |
H3D | 0.351 (5) | 0.5763 (13) | 0.714 (3) | 0.020* | |
H3E | 0.610 (5) | 0.5800 (13) | 0.718 (3) | 0.020* | |
O2W | 0.9919 (4) | 0.63300 (9) | 0.75833 (19) | 0.0207 (4) | |
H4A | 0.984 (6) | 0.6528 (14) | 0.688 (3) | 0.025* | |
H4B | 1.048 (6) | 0.6569 (14) | 0.820 (3) | 0.025* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.01858 (12) | 0.01419 (11) | 0.01396 (11) | −0.00378 (8) | 0.00117 (8) | −0.00216 (7) |
Mn1 | 0.00871 (19) | 0.0086 (2) | 0.0109 (2) | 0.00049 (15) | 0.00185 (15) | 0.00159 (15) |
O1 | 0.0104 (7) | 0.0106 (7) | 0.0134 (7) | −0.0006 (5) | 0.0022 (6) | 0.0013 (5) |
O2 | 0.0101 (7) | 0.0127 (7) | 0.0152 (7) | 0.0019 (5) | 0.0031 (6) | 0.0031 (5) |
C1 | 0.0114 (9) | 0.0078 (8) | 0.0120 (9) | −0.0005 (7) | 0.0005 (7) | −0.0018 (7) |
C2 | 0.0114 (9) | 0.0149 (9) | 0.0134 (10) | 0.0022 (8) | 0.0023 (8) | 0.0024 (7) |
C3 | 0.0239 (12) | 0.0231 (11) | 0.0134 (10) | 0.0054 (9) | −0.0007 (9) | −0.0019 (8) |
N1 | 0.0109 (8) | 0.0119 (8) | 0.0143 (9) | 0.0014 (6) | 0.0010 (7) | 0.0037 (7) |
O1W | 0.0149 (8) | 0.0157 (8) | 0.0194 (8) | −0.0006 (6) | 0.0043 (7) | −0.0043 (6) |
O2W | 0.0238 (9) | 0.0221 (9) | 0.0155 (9) | −0.0044 (7) | 0.0026 (7) | −0.0042 (6) |
Geometric parameters (Å, º) top
Mn1—O1i | 2.1595 (14) | C2—H2 | 1.0000 |
Mn1—O1 | 2.1595 (14) | C3—H3A | 0.9800 |
Mn1—O1Wi | 2.1799 (16) | C3—H3B | 0.9800 |
Mn1—O1W | 2.1799 (16) | C3—H3C | 0.9800 |
Mn1—O2ii | 2.1811 (14) | N1—H1A | 0.890 (17) |
Mn1—O2iii | 2.1811 (14) | N1—H1B | 0.899 (17) |
O1—C1 | 1.247 (2) | N1—H1C | 0.886 (17) |
O2—C1 | 1.261 (2) | O1W—H3D | 0.752 (19) |
O2—Mn1iv | 2.1811 (14) | O1W—H3E | 0.73 (2) |
C1—C2 | 1.534 (3) | O2W—H4A | 0.75 (2) |
C2—N1 | 1.485 (3) | O2W—H4B | 0.74 (2) |
C2—C3 | 1.519 (3) | | |
| | | |
O1i—Mn1—O1 | 180.00 (6) | N1—C2—C1 | 108.25 (16) |
O1i—Mn1—O1Wi | 88.50 (6) | C3—C2—C1 | 110.88 (17) |
O1—Mn1—O1Wi | 91.50 (6) | N1—C2—H2 | 109.1 |
O1i—Mn1—O1W | 91.50 (6) | C3—C2—H2 | 109.1 |
O1—Mn1—O1W | 88.50 (6) | C1—C2—H2 | 109.1 |
O1Wi—Mn1—O1W | 180.0 | C2—C3—H3A | 109.5 |
O1i—Mn1—O2ii | 94.90 (5) | C2—C3—H3B | 109.5 |
O1—Mn1—O2ii | 85.10 (5) | H3A—C3—H3B | 109.5 |
O1Wi—Mn1—O2ii | 85.16 (6) | C2—C3—H3C | 109.5 |
O1W—Mn1—O2ii | 94.84 (6) | H3A—C3—H3C | 109.5 |
O1i—Mn1—O2iii | 85.10 (5) | H3B—C3—H3C | 109.5 |
O1—Mn1—O2iii | 94.90 (5) | C2—N1—H1A | 110.6 (16) |
O1Wi—Mn1—O2iii | 94.84 (6) | C2—N1—H1B | 109.5 (16) |
O1W—Mn1—O2iii | 85.16 (6) | H1A—N1—H1B | 108 (2) |
O2ii—Mn1—O2iii | 180.0 | C2—N1—H1C | 111.1 (16) |
C1—O1—Mn1 | 139.35 (13) | H1A—N1—H1C | 108 (2) |
C1—O2—Mn1iv | 128.09 (13) | H1B—N1—H1C | 109 (2) |
O1—C1—O2 | 126.02 (19) | Mn1—O1W—H3D | 125 (2) |
O1—C1—C2 | 119.12 (17) | Mn1—O1W—H3E | 109 (2) |
O2—C1—C2 | 114.86 (17) | H3D—O1W—H3E | 112 (3) |
N1—C2—C3 | 110.36 (17) | H4A—O2W—H4B | 106 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iii) −x+2, −y+1, −z+1; (iv) x+1, y, z. |
Crystal data top
C6H18MnN2O6·2(I)·2(H2O) | F(000) = 534 |
Mr = 558.99 | Dx = 2.062 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 4.794 (3) Å | Cell parameters from 265 reflections |
b = 20.114 (11) Å | θ = 2.4–18.2° |
c = 9.482 (5) Å | µ = 4.19 mm−1 |
β = 100.047 (10)° | T = 100 K |
V = 900.3 (9) Å3 | Needle, colourless |
Z = 2 | 0.23 × 0.04 × 0.02 mm |
Data collection top
Bruker APEX CCD diffractometer | 3312 independent reflections |
Radiation source: microsource | 2231 reflections with I > 2σ(I) |
Multilayer optics monochromator | θmax = 26.4°, θmin = 2.4° |
ω scans | h = −5→5 |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | k = 0→25 |
Tmin = 0.327, Tmax = 0.745 | l = 0→11 |
3312 measured reflections | |
Refinement top
Refinement on F2 | 6 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.063 | H 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 reflections | Δρmax = 1.07 e Å−3 |
111 parameters | Δρmin = −1.76 e Å−3 |
Crystal data top
C6H18MnN2O6·2(I)·2(H2O) | V = 900.3 (9) Å3 |
Mr = 558.99 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 4.794 (3) Å | µ = 4.19 mm−1 |
b = 20.114 (11) Å | T = 100 K |
c = 9.482 (5) Å | 0.23 × 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 = 0.745 | 2231 reflections with I > 2σ(I) |
Refinement top
R[F2 > 2σ(F2)] = 0.063 | 6 restraints |
wR(F2) = 0.143 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 1.07 e Å−3 |
3312 reflections | Δρmin = −1.76 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
I1 | 1.16518 (16) | 0.74663 (3) | 0.50202 (7) | 0.0201 (2) | |
Mn1 | 0.5000 | 0.5000 | 0.5000 | 0.0156 (5) | |
O1 | 0.8296 (15) | 0.5664 (3) | 0.4572 (7) | 0.0158 (16) | |
O2 | 1.2155 (15) | 0.5634 (3) | 0.3541 (7) | 0.0165 (16) | |
C1 | 0.963 (2) | 0.5804 (4) | 0.3597 (11) | 0.015 (2) | |
C2 | 0.815 (2) | 0.6226 (5) | 0.2343 (11) | 0.018 (2) | |
H2 | 0.9558 | 0.6551 | 0.2083 | 0.021* | |
C3 | 0.711 (3) | 0.5799 (5) | 0.1055 (11) | 0.023 (2) | |
H3A | 0.5604 | 0.5504 | 0.1264 | 0.034* | |
H3B | 0.8677 | 0.5532 | 0.0825 | 0.034* | |
H3C | 0.6358 | 0.6083 | 0.0236 | 0.034* | |
N1 | 0.584 (2) | 0.6600 (4) | 0.2804 (10) | 0.0172 (19) | |
H1A | 0.48 (2) | 0.684 (4) | 0.207 (8) | 0.021* | |
H1B | 0.65 (2) | 0.689 (4) | 0.355 (8) | 0.021* | |
H1C | 0.439 (17) | 0.631 (4) | 0.290 (11) | 0.021* | |
O3 | 0.4664 (18) | 0.5568 (4) | 0.6922 (9) | 0.024 (2) | |
H3D | 0.333 (19) | 0.581 (5) | 0.696 (13) | 0.028* | |
H3E | 0.57 (2) | 0.588 (5) | 0.700 (12) | 0.028* | |
O4 | 0.9751 (19) | 0.6267 (4) | 0.7476 (8) | 0.025 (2) | |
H4B | 0.96 (3) | 0.651 (5) | 0.814 (6) | 0.030* | |
H4A | 0.96 (3) | 0.651 (5) | 0.678 (6) | 0.030* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0220 (4) | 0.0186 (4) | 0.0193 (4) | −0.0021 (3) | 0.0023 (3) | −0.0029 (3) |
Mn1 | 0.0135 (12) | 0.0159 (11) | 0.0177 (11) | −0.0003 (10) | 0.0034 (10) | 0.0022 (9) |
O1 | 0.018 (4) | 0.015 (3) | 0.015 (4) | −0.001 (3) | 0.002 (3) | 0.003 (3) |
O2 | 0.014 (4) | 0.016 (4) | 0.022 (4) | 0.001 (3) | 0.010 (3) | 0.003 (3) |
C1 | 0.016 (6) | 0.009 (5) | 0.022 (6) | −0.001 (5) | 0.004 (5) | 0.000 (4) |
C2 | 0.012 (6) | 0.016 (5) | 0.027 (6) | 0.002 (4) | 0.006 (5) | 0.001 (4) |
C3 | 0.026 (7) | 0.026 (6) | 0.016 (5) | 0.004 (5) | 0.001 (5) | 0.001 (4) |
N1 | 0.013 (5) | 0.014 (4) | 0.023 (5) | 0.001 (4) | 0.002 (5) | 0.001 (4) |
O3 | 0.023 (5) | 0.012 (4) | 0.037 (5) | 0.001 (3) | 0.008 (4) | −0.003 (3) |
O4 | 0.033 (5) | 0.028 (5) | 0.015 (4) | −0.007 (4) | 0.007 (4) | −0.002 (3) |
Geometric parameters (Å, º) top
Mn1—O1i | 2.161 (7) | C2—H2 | 1.0000 |
Mn1—O1 | 2.161 (7) | C3—H3A | 0.9800 |
Mn1—O2ii | 2.177 (7) | C3—H3B | 0.9800 |
Mn1—O2iii | 2.177 (7) | C3—H3C | 0.9800 |
Mn1—O3i | 2.180 (8) | N1—H1A | 0.93 (5) |
Mn1—O3 | 2.180 (8) | N1—H1B | 0.93 (5) |
O1—C1 | 1.243 (12) | N1—H1C | 0.93 (5) |
O2—C1 | 1.270 (12) | O3—H3D | 0.81 (7) |
O2—Mn1iv | 2.177 (7) | O3—H3E | 0.80 (7) |
C1—C2 | 1.530 (13) | O4—H4B | 0.81 (5) |
C2—N1 | 1.467 (13) | O4—H4A | 0.81 (5) |
C2—C3 | 1.507 (13) | | |
| | | |
O1i—Mn1—O1 | 180.0 (3) | N1—C2—C1 | 108.9 (8) |
O1i—Mn1—O2ii | 85.2 (3) | C3—C2—C1 | 110.9 (8) |
O1—Mn1—O2ii | 94.8 (3) | N1—C2—H2 | 108.4 |
O1i—Mn1—O2iii | 94.8 (3) | C3—C2—H2 | 108.4 |
O1—Mn1—O2iii | 85.2 (3) | C1—C2—H2 | 108.4 |
O2ii—Mn1—O2iii | 180.0 | C2—C3—H3A | 109.5 |
O1i—Mn1—O3i | 89.8 (3) | C2—C3—H3B | 109.5 |
O1—Mn1—O3i | 90.2 (3) | H3A—C3—H3B | 109.5 |
O2ii—Mn1—O3i | 95.5 (3) | C2—C3—H3C | 109.5 |
O2iii—Mn1—O3i | 84.5 (3) | H3A—C3—H3C | 109.5 |
O1i—Mn1—O3 | 90.2 (3) | H3B—C3—H3C | 109.5 |
O1—Mn1—O3 | 89.8 (3) | C2—N1—H1A | 113 (7) |
O2ii—Mn1—O3 | 84.5 (3) | C2—N1—H1B | 112 (7) |
O2iii—Mn1—O3 | 95.5 (3) | H1A—N1—H1B | 108 (9) |
O3i—Mn1—O3 | 180.0 | C2—N1—H1C | 109 (7) |
C1—O1—Mn1 | 140.0 (6) | H1A—N1—H1C | 94 (9) |
C1—O2—Mn1iv | 128.9 (6) | H1B—N1—H1C | 119 (9) |
O1—C1—O2 | 126.0 (9) | Mn1—O3—H3D | 121 (9) |
O1—C1—C2 | 118.5 (9) | Mn1—O3—H3E | 110 (9) |
O2—C1—C2 | 115.6 (9) | H3D—O3—H3E | 92 (10) |
N1—C2—C3 | 111.8 (9) | H4B—O4—H4A | 106 (9) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1; (iii) x−1, y, z; (iv) x+1, y, z. |
Experimental details
| (8) | (9) | (10) |
Crystal data |
Chemical formula | C6H18MnN2O6·2(Cl)·2(H2O) | C6H18MnN2O6·2(Br)·2(H2O) | C6H18MnN2O6·2(I)·2(H2O) |
Mr | 376.09 | 465.01 | 558.99 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/c |
Temperature (K) | 100 | 100 | 100 |
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) |
V (Å3) | 797.1 (3) | 836.72 (18) | 900.3 (9) |
Z | 2 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 1.19 | 5.59 | 4.19 |
Crystal size (mm) | 0.40 × 0.07 × 0.07 | 0.30 × 0.07 × 0.07 | 0.23 × 0.04 × 0.02 |
|
Data collection |
Diffractometer | Bruker APEX-II CCD diffractometer | Bruker APEX-II CCD diffractometer | Bruker APEX CCD diffractometer |
Absorption correction | Multi-scan SADABS | Multi-scan SADABS (Sheldrick, 1996) | Multi-scan SADABS (Sheldrick, 1996) |
Tmin, Tmax | 0.565, 0.745 | 0.507, 0.746 | 0.327, 0.745 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9455, 1637, 1419 | 12568, 2500, 2207 | 3312, 3312, 2231 |
Rint | 0.069 | 0.043 | ? |
(sin θ/λ)max (Å−1) | 0.628 | 0.720 | 0.625 |
|
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 reflections | 1637 | 2500 | 3312 |
No. of parameters | 110 | 110 | 111 |
No. of restraints | 5 | 5 | 6 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.41, −0.28 | 0.83, −0.43 | 1.07, −1.76 |
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