metal-organic compounds
The title complex, {[Mn(C7H3NO4)(C12H8N2)]·H2O}n, conventionally abbreviated to {[Mn(2,3-pddc)(phen)]·H2O}n (phen is 1,10-phenanthroline and 2,3-pddc is 2,3-pyridinedicarboxylate), has been synthesized under hydrothermal conditions. In the complex, the Mn atom is coordinated by three O atoms of three symmetry-equivalent 2,3-pddc molecules. The complex thus extends in two dimensions, resulting in the formation of a two-dimensional network structure. The complex is further assembled into a three-dimensional network by π–π stacking interactions involving the phen ligands.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805035257/su6239sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805035257/su6239Isup2.hkl |
CCDC reference: 277912
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
Crystal data top
[Mn(C12H8N2)(C7H3NO4)]·H2O | F(000) = 852 |
Mr = 418.26 | Dx = 1.621 Mg m−3 |
Monoclinic, P21/n | Melting point > 300 K |
Hall symbol: -P 2ybn | Mo Kα radiation, λ = 0.71073 Å |
a = 11.649 (4) Å | Cell parameters from 1897 reflections |
b = 11.774 (4) Å | θ = 2.4–23.9° |
c = 13.292 (4) Å | µ = 0.81 mm−1 |
β = 109.939 (5)° | T = 298 K |
V = 1713.6 (9) Å3 | Rod, yellow |
Z = 4 | 0.38 × 0.35 × 0.29 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 4136 independent reflections |
Radiation source: fine-focus sealed tube | 2336 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
φ and ω scans | θmax = 28.4°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→13 |
Tmin = 0.748, Tmax = 0.799 | k = −15→15 |
10888 measured reflections | l = −17→16 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.196 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.1091P)2] where P = (Fo2 + 2Fc2)/3 |
4136 reflections | (Δ/σ)max = 0.001 |
259 parameters | Δρmax = 0.65 e Å−3 |
403 restraints | Δρmin = −0.84 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Mn1 | 0.96099 (5) | 0.91660 (5) | 0.82927 (5) | 0.0279 (2) | |
N1 | 0.7678 (3) | 0.8427 (3) | 0.7819 (3) | 0.0298 (8) | |
N2 | 0.8964 (4) | 1.0262 (3) | 0.6736 (3) | 0.0436 (9) | |
N3 | 1.1266 (3) | 0.9953 (3) | 0.8108 (3) | 0.0392 (9) | |
O1 | 0.8457 (3) | 0.6427 (3) | 0.6186 (2) | 0.0375 (7) | |
O2 | 0.9577 (2) | 0.7699 (2) | 0.7340 (2) | 0.0358 (7) | |
O3 | 0.6049 (2) | 0.5376 (2) | 0.5869 (2) | 0.0324 (7) | |
O4 | 0.5624 (3) | 0.6788 (2) | 0.4688 (2) | 0.0375 (7) | |
O5 | 0.5104 (9) | 0.9206 (6) | 0.4219 (7) | 0.203 (4) | |
C1 | 0.7470 (3) | 0.7637 (3) | 0.7064 (3) | 0.0271 (8) | |
C2 | 0.6282 (4) | 0.7268 (3) | 0.6506 (3) | 0.0293 (9) | |
C3 | 0.5338 (3) | 0.7657 (3) | 0.6736 (3) | 0.0240 (8) | |
H3 | 0.4548 | 0.7402 | 0.6375 | 0.029* | |
C4 | 0.5569 (4) | 0.8427 (4) | 0.7507 (4) | 0.0450 (11) | |
H4 | 0.4921 | 0.8715 | 0.7686 | 0.054* | |
C5 | 0.6730 (4) | 0.8818 (4) | 0.8054 (4) | 0.0377 (10) | |
H5 | 0.6850 | 0.9359 | 0.8590 | 0.045* | |
C6 | 0.8595 (3) | 0.7200 (3) | 0.6836 (3) | 0.0258 (8) | |
C7 | 0.5969 (3) | 0.6389 (4) | 0.5620 (3) | 0.0286 (9) | |
C8 | 0.7824 (5) | 1.0457 (5) | 0.6077 (4) | 0.0629 (15) | |
H8 | 0.7178 | 1.0152 | 0.6248 | 0.075* | |
C9 | 0.7565 (7) | 1.1097 (6) | 0.5148 (5) | 0.0800 (19) | |
H9 | 0.6759 | 1.1217 | 0.4712 | 0.096* | |
C10 | 0.8485 (7) | 1.1543 (5) | 0.4882 (5) | 0.0759 (17) | |
H10 | 0.8319 | 1.1959 | 0.4254 | 0.091* | |
C11 | 0.9679 (6) | 1.1380 (5) | 0.5546 (4) | 0.0601 (14) | |
C12 | 1.0703 (7) | 1.1886 (5) | 0.5362 (5) | 0.0798 (18) | |
H12 | 1.0573 | 1.2332 | 0.4755 | 0.096* | |
C13 | 1.1823 (7) | 1.1742 (5) | 0.6025 (5) | 0.0777 (18) | |
H13 | 1.2468 | 1.2064 | 0.5863 | 0.093* | |
C14 | 1.2077 (6) | 1.1096 (4) | 0.6996 (5) | 0.0570 (14) | |
C15 | 1.3247 (6) | 1.0938 (5) | 0.7744 (6) | 0.0738 (17) | |
H15 | 1.3917 | 1.1261 | 0.7625 | 0.089* | |
C16 | 1.3413 (5) | 1.0315 (5) | 0.8644 (5) | 0.0654 (15) | |
H16 | 1.4191 | 1.0211 | 0.9142 | 0.078* | |
C17 | 1.2392 (4) | 0.9832 (4) | 0.8807 (4) | 0.0509 (13) | |
H17 | 1.2504 | 0.9412 | 0.9426 | 0.061* | |
C18 | 1.1102 (5) | 1.0573 (4) | 0.7210 (4) | 0.0422 (11) | |
C19 | 0.9883 (5) | 1.0721 (4) | 0.6482 (4) | 0.0423 (11) | |
H2 | 0.541 (5) | 0.8578 (12) | 0.462 (3) | 0.080* | |
H1 | 0.566 (2) | 0.970 (2) | 0.460 (3) | 0.080* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.0294 (4) | 0.0266 (4) | 0.0235 (3) | −0.0032 (3) | 0.0036 (2) | −0.0009 (3) |
N1 | 0.0317 (18) | 0.0266 (18) | 0.0301 (17) | −0.0039 (15) | 0.0093 (14) | −0.0076 (15) |
N2 | 0.056 (2) | 0.039 (2) | 0.0319 (19) | −0.0004 (19) | 0.0090 (18) | 0.0037 (17) |
N3 | 0.043 (2) | 0.036 (2) | 0.038 (2) | −0.0099 (17) | 0.0129 (17) | −0.0028 (17) |
O1 | 0.0413 (17) | 0.0344 (17) | 0.0375 (17) | −0.0062 (14) | 0.0143 (13) | −0.0156 (14) |
O2 | 0.0226 (14) | 0.0417 (18) | 0.0374 (16) | −0.0026 (13) | 0.0029 (12) | −0.0123 (14) |
O3 | 0.0353 (16) | 0.0235 (15) | 0.0334 (16) | −0.0013 (12) | 0.0051 (13) | 0.0023 (13) |
O4 | 0.0467 (17) | 0.0308 (16) | 0.0243 (15) | −0.0075 (14) | −0.0018 (13) | 0.0007 (12) |
O5 | 0.228 (10) | 0.137 (7) | 0.200 (10) | 0.003 (6) | 0.015 (7) | 0.027 (6) |
C1 | 0.028 (2) | 0.0236 (19) | 0.0267 (19) | −0.0011 (16) | 0.0052 (16) | 0.0015 (16) |
C2 | 0.034 (2) | 0.025 (2) | 0.0278 (19) | −0.0019 (17) | 0.0088 (17) | 0.0000 (16) |
C3 | 0.0093 (16) | 0.029 (2) | 0.0311 (19) | −0.0041 (15) | 0.0038 (14) | −0.0097 (17) |
C4 | 0.040 (2) | 0.043 (3) | 0.056 (3) | 0.002 (2) | 0.022 (2) | −0.008 (2) |
C5 | 0.038 (2) | 0.035 (2) | 0.043 (2) | −0.0020 (19) | 0.017 (2) | −0.015 (2) |
C6 | 0.030 (2) | 0.025 (2) | 0.0213 (18) | 0.0009 (16) | 0.0074 (16) | 0.0012 (16) |
C7 | 0.0223 (19) | 0.030 (2) | 0.030 (2) | −0.0044 (17) | 0.0039 (16) | −0.0020 (18) |
C8 | 0.066 (3) | 0.061 (3) | 0.045 (3) | 0.003 (3) | −0.002 (3) | 0.015 (3) |
C9 | 0.089 (4) | 0.075 (4) | 0.053 (3) | 0.010 (3) | −0.005 (3) | 0.022 (3) |
C10 | 0.109 (4) | 0.069 (4) | 0.042 (3) | 0.015 (4) | 0.016 (3) | 0.025 (3) |
C11 | 0.099 (4) | 0.047 (3) | 0.045 (3) | 0.004 (3) | 0.038 (3) | 0.011 (2) |
C12 | 0.124 (5) | 0.067 (4) | 0.068 (4) | 0.002 (4) | 0.057 (4) | 0.018 (3) |
C13 | 0.105 (4) | 0.064 (4) | 0.091 (4) | −0.016 (4) | 0.069 (4) | 0.013 (3) |
C14 | 0.072 (3) | 0.044 (3) | 0.072 (3) | −0.012 (3) | 0.046 (3) | 0.000 (3) |
C15 | 0.068 (4) | 0.068 (4) | 0.100 (4) | −0.027 (3) | 0.048 (3) | −0.014 (3) |
C16 | 0.046 (3) | 0.070 (4) | 0.080 (4) | −0.017 (3) | 0.021 (3) | −0.014 (3) |
C17 | 0.046 (3) | 0.055 (3) | 0.052 (3) | −0.015 (2) | 0.018 (2) | −0.009 (2) |
C18 | 0.056 (3) | 0.034 (2) | 0.046 (3) | −0.007 (2) | 0.029 (2) | −0.003 (2) |
C19 | 0.070 (3) | 0.032 (2) | 0.030 (2) | −0.005 (2) | 0.024 (2) | 0.0025 (18) |
Geometric parameters (Å, º) top
Mn1—O3i | 2.108 (3) | C3—H3 | 0.9300 |
Mn1—O2 | 2.134 (3) | C4—C5 | 1.378 (6) |
Mn1—O4ii | 2.145 (3) | C4—H4 | 0.9300 |
Mn1—N3 | 2.228 (4) | C5—H5 | 0.9300 |
Mn1—N1 | 2.292 (3) | C8—C9 | 1.389 (8) |
Mn1—N2 | 2.335 (4) | C8—H8 | 0.9300 |
N1—C5 | 1.328 (5) | C9—C10 | 1.344 (9) |
N1—C1 | 1.329 (5) | C9—H9 | 0.9300 |
N2—C8 | 1.338 (6) | C10—C11 | 1.384 (8) |
N2—C19 | 1.341 (6) | C10—H10 | 0.9300 |
N3—C17 | 1.332 (6) | C11—C19 | 1.415 (6) |
N3—C18 | 1.355 (6) | C11—C12 | 1.427 (8) |
O1—C6 | 1.227 (4) | C12—C13 | 1.313 (8) |
O2—C6 | 1.257 (4) | C12—H12 | 0.9300 |
O3—C7 | 1.233 (5) | C13—C14 | 1.439 (8) |
O3—Mn1iii | 2.108 (3) | C13—H13 | 0.9300 |
O4—C7 | 1.256 (4) | C14—C15 | 1.399 (9) |
O4—Mn1iv | 2.145 (3) | C14—C18 | 1.404 (7) |
O5—H2 | 0.909 (18) | C15—C16 | 1.358 (9) |
O5—H1 | 0.887 (18) | C15—H15 | 0.9300 |
C1—C2 | 1.398 (5) | C16—C17 | 1.401 (7) |
C1—C6 | 1.531 (5) | C16—H16 | 0.9300 |
C2—C3 | 1.320 (5) | C17—H17 | 0.9300 |
C2—C7 | 1.516 (5) | C18—C19 | 1.431 (7) |
C3—C4 | 1.325 (6) | ||
O3i—Mn1—O2 | 157.58 (11) | O1—C6—O2 | 126.8 (4) |
O3i—Mn1—O4ii | 95.12 (11) | O1—C6—C1 | 118.2 (3) |
O2—Mn1—O4ii | 88.98 (11) | O2—C6—C1 | 115.0 (3) |
O3i—Mn1—N3 | 105.21 (13) | O3—C7—O4 | 126.6 (4) |
O2—Mn1—N3 | 96.45 (12) | O3—C7—C2 | 118.5 (3) |
O4ii—Mn1—N3 | 94.07 (13) | O4—C7—C2 | 115.0 (4) |
O3i—Mn1—N1 | 84.32 (11) | N2—C8—C9 | 122.8 (6) |
O2—Mn1—N1 | 73.30 (11) | N2—C8—H8 | 118.6 |
O4ii—Mn1—N1 | 103.78 (12) | C9—C8—H8 | 118.6 |
N3—Mn1—N1 | 159.03 (13) | C10—C9—C8 | 119.6 (6) |
O3i—Mn1—N2 | 91.69 (13) | C10—C9—H9 | 120.2 |
O2—Mn1—N2 | 89.23 (12) | C8—C9—H9 | 120.2 |
O4ii—Mn1—N2 | 166.30 (13) | C9—C10—C11 | 119.8 (5) |
N3—Mn1—N2 | 72.64 (14) | C9—C10—H10 | 120.1 |
N1—Mn1—N2 | 88.69 (13) | C11—C10—H10 | 120.1 |
C5—N1—C1 | 117.9 (3) | C10—C11—C19 | 117.8 (5) |
C5—N1—Mn1 | 128.4 (3) | C10—C11—C12 | 123.4 (6) |
C1—N1—Mn1 | 112.5 (2) | C19—C11—C12 | 118.7 (6) |
C8—N2—C19 | 117.7 (4) | C13—C12—C11 | 121.9 (6) |
C8—N2—Mn1 | 128.5 (4) | C13—C12—H12 | 119.1 |
C19—N2—Mn1 | 113.7 (3) | C11—C12—H12 | 119.1 |
C17—N3—C18 | 118.8 (4) | C12—C13—C14 | 121.6 (6) |
C17—N3—Mn1 | 124.2 (3) | C12—C13—H13 | 119.2 |
C18—N3—Mn1 | 117.0 (3) | C14—C13—H13 | 119.2 |
C6—O2—Mn1 | 121.5 (2) | C15—C14—C18 | 117.1 (5) |
C7—O3—Mn1iii | 142.0 (3) | C15—C14—C13 | 124.1 (5) |
C7—O4—Mn1iv | 123.6 (3) | C18—C14—C13 | 118.7 (6) |
H2—O5—H1 | 97 (3) | C16—C15—C14 | 120.7 (5) |
N1—C1—C2 | 120.7 (4) | C16—C15—H15 | 119.7 |
N1—C1—C6 | 115.9 (3) | C14—C15—H15 | 119.7 |
C2—C1—C6 | 123.3 (3) | C15—C16—C17 | 118.8 (6) |
C3—C2—C1 | 121.4 (4) | C15—C16—H16 | 120.6 |
C3—C2—C7 | 114.7 (3) | C17—C16—H16 | 120.6 |
C1—C2—C7 | 123.8 (3) | N3—C17—C16 | 122.3 (5) |
C2—C3—C4 | 116.8 (4) | N3—C17—H17 | 118.8 |
C2—C3—H3 | 121.6 | C16—C17—H17 | 118.8 |
C4—C3—H3 | 121.6 | N3—C18—C14 | 122.3 (5) |
C3—C4—C5 | 122.7 (4) | N3—C18—C19 | 118.1 (4) |
C3—C4—H4 | 118.6 | C14—C18—C19 | 119.6 (5) |
C5—C4—H4 | 118.6 | N2—C19—C11 | 122.2 (5) |
N1—C5—C4 | 120.3 (4) | N2—C19—C18 | 118.3 (4) |
N1—C5—H5 | 119.8 | C11—C19—C18 | 119.5 (5) |
C4—C5—H5 | 119.8 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) x+1/2, −y+3/2, z+1/2; (iii) −x+3/2, y−1/2, −z+3/2; (iv) x−1/2, −y+3/2, z−1/2. |