In the title compound, [Mn(C
14H
8N
2O
6)
2(H
2O)
4]
n, each 6,6′-dihydroxy-3,3-diazenediyldibenzoate ligand acts as a carboxylate bridge, leading to the formation of polymeric chains running in the [110] direction. The Mn atom is hexacoordinated in a distorted octahedral geometry by six O atoms [Mn—O = 2.1412 (16)–2.2262 (17) Å] from two organic ligands and four water molecules. The crystal packing is stabilized by π–π interactions and intermolecular O—H
O and O—H
N hydrogen bonds.
Supporting information
CCDC reference: 642953
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.029
- wR factor = 0.070
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Mn1
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 28.33
From the CIF: _reflns_number_total 3620
Count of symmetry unique reflns 2410
Completeness (_total/calc) 150.21%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1210
Fraction of Friedel pairs measured 0.502
Are heavy atom types Z>Si present yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
catena-Poly[[tetraaquamanganese(II)]-µ-6,6'-dihydroxy-3,3-
diazenediyldibenzoato-
κ2O:
O']
top
Crystal data top
[Mn(C14H8N2O6)2(H2O)4] | Dx = 1.758 Mg m−3 |
Mr = 427.23 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P43212 | Cell parameters from 935 reflections |
Hall symbol: P 4nw 2abw | θ = 2.1–26° |
a = 10.2694 (13) Å | µ = 0.88 mm−1 |
c = 30.611 (8) Å | T = 293 K |
V = 3228.2 (10) Å3 | Block, orange |
Z = 8 | 0.18 × 0.14 × 0.12 mm |
F(000) = 1752 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3620 independent reflections |
Radiation source: fine-focus sealed tube | 3153 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
φ and ω scans | θmax = 28.3°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −11→13 |
Tmin = 0.86, Tmax = 0.90 | k = −11→12 |
18659 measured reflections | l = −38→39 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | H-atom parameters constrained |
wR(F2) = 0.070 | w = 1/[σ2(Fo2) + (0.0368P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max < 0.001 |
3620 reflections | Δρmax = 0.30 e Å−3 |
239 parameters | Δρmin = −0.42 e Å−3 |
12 restraints | Absolute structure: Flack (1983), 1210 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.003 (16) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Mn1 | 0.31207 (3) | 0.96108 (3) | 0.142844 (10) | 0.02553 (9) | |
O1W | 0.33240 (17) | 0.80000 (17) | 0.09491 (5) | 0.0435 (4) | |
H1WA | 0.3895 | 0.8146 | 0.0755 | 0.065* | |
H1WB | 0.2693 | 0.7577 | 0.0841 | 0.065* | |
O2 | 1.11938 (17) | 0.24608 (17) | 0.14725 (5) | 0.0405 (4) | |
O2W | 0.50673 (16) | 1.02057 (18) | 0.12576 (6) | 0.0462 (4) | |
H2WA | 0.5424 | 1.0932 | 0.1199 | 0.069* | |
H2WB | 0.5549 | 0.9782 | 0.1433 | 0.069* | |
O3 | 0.35369 (17) | 0.84367 (17) | 0.28231 (5) | 0.0430 (4) | |
H3A | 0.3428 | 0.8720 | 0.2575 | 0.052* | |
O3W | 0.23079 (16) | 1.07358 (16) | 0.09064 (5) | 0.0415 (4) | |
H3WA | 0.1925 | 1.1409 | 0.1003 | 0.062* | |
H3WB | 0.2401 | 1.0792 | 0.0632 | 0.062* | |
O4 | 0.39386 (15) | 0.86759 (16) | 0.19998 (5) | 0.0334 (4) | |
O4W | 0.12448 (17) | 0.85805 (19) | 0.15441 (5) | 0.0442 (4) | |
H4WA | 0.1314 | 0.8099 | 0.1769 | 0.066* | |
H4WB | 0.0908 | 0.8144 | 0.1337 | 0.066* | |
O5 | 0.57627 (16) | 0.78864 (16) | 0.17102 (5) | 0.0357 (4) | |
O6 | 1.18617 (17) | 0.06247 (16) | 0.26542 (5) | 0.0428 (4) | |
H6A | 1.2242 | 0.0549 | 0.2420 | 0.051* | |
N1 | 0.80204 (18) | 0.44061 (18) | 0.25395 (6) | 0.0302 (4) | |
N2 | 0.74338 (18) | 0.47035 (18) | 0.28867 (6) | 0.0293 (4) | |
O1 | 1.23776 (16) | 0.10721 (15) | 0.18662 (5) | 0.0341 (4) | |
C2 | 0.4791 (2) | 0.6890 (2) | 0.32062 (7) | 0.0329 (5) | |
H2B | 0.4319 | 0.7073 | 0.3458 | 0.039* | |
C3 | 1.0101 (2) | 0.1727 (2) | 0.29780 (7) | 0.0321 (5) | |
H3B | 1.0209 | 0.1222 | 0.3227 | 0.038* | |
C4 | 1.0720 (2) | 0.2238 (2) | 0.22317 (7) | 0.0262 (5) | |
C5 | 0.4507 (2) | 0.7540 (2) | 0.28193 (7) | 0.0279 (5) | |
C6 | 0.8987 (2) | 0.3420 (2) | 0.25912 (7) | 0.0273 (5) | |
C7 | 0.6465 (2) | 0.5676 (2) | 0.28398 (7) | 0.0267 (5) | |
C8 | 0.4969 (2) | 0.7982 (2) | 0.20195 (7) | 0.0270 (5) | |
C9 | 0.6194 (2) | 0.6342 (2) | 0.24557 (7) | 0.0256 (5) | |
H9A | 0.6672 | 0.6156 | 0.2205 | 0.031* | |
C10 | 1.0906 (2) | 0.1525 (2) | 0.26152 (7) | 0.0286 (5) | |
C11 | 0.9760 (2) | 0.3190 (2) | 0.22291 (7) | 0.0281 (5) | |
H11A | 0.9634 | 0.3685 | 0.1978 | 0.034* | |
C12 | 0.5227 (2) | 0.72763 (19) | 0.24386 (7) | 0.0245 (4) | |
C13 | 0.5760 (2) | 0.5984 (2) | 0.32171 (7) | 0.0309 (5) | |
H13A | 0.5956 | 0.5565 | 0.3478 | 0.037* | |
C14 | 0.9156 (2) | 0.2664 (2) | 0.29672 (7) | 0.0295 (5) | |
H14A | 0.8626 | 0.2799 | 0.3209 | 0.035* | |
C1 | 1.1470 (2) | 0.1928 (2) | 0.18252 (7) | 0.0295 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Mn1 | 0.02670 (18) | 0.02635 (17) | 0.02353 (15) | 0.00340 (14) | 0.00019 (14) | 0.00063 (13) |
O1W | 0.0451 (10) | 0.0418 (10) | 0.0435 (10) | −0.0039 (9) | 0.0007 (9) | −0.0126 (8) |
O2 | 0.0487 (10) | 0.0430 (10) | 0.0297 (8) | 0.0185 (8) | 0.0010 (8) | 0.0022 (8) |
O2W | 0.0319 (9) | 0.0515 (11) | 0.0551 (10) | −0.0063 (8) | −0.0049 (8) | 0.0242 (9) |
O3 | 0.0428 (10) | 0.0523 (11) | 0.0339 (9) | 0.0268 (8) | 0.0079 (8) | 0.0098 (8) |
O3W | 0.0503 (11) | 0.0448 (10) | 0.0294 (8) | 0.0176 (8) | 0.0027 (8) | 0.0078 (7) |
O4 | 0.0276 (9) | 0.0396 (9) | 0.0329 (8) | 0.0110 (7) | −0.0002 (7) | 0.0075 (7) |
O4W | 0.0436 (11) | 0.0535 (12) | 0.0354 (9) | −0.0154 (8) | 0.0018 (8) | 0.0044 (8) |
O5 | 0.0366 (9) | 0.0410 (10) | 0.0294 (8) | 0.0112 (7) | 0.0065 (7) | 0.0065 (7) |
O6 | 0.0497 (11) | 0.0449 (10) | 0.0337 (9) | 0.0282 (9) | −0.0025 (8) | 0.0025 (8) |
N1 | 0.0286 (10) | 0.0312 (10) | 0.0309 (9) | 0.0076 (8) | 0.0031 (8) | 0.0036 (8) |
N2 | 0.0299 (10) | 0.0277 (10) | 0.0303 (10) | 0.0062 (8) | 0.0014 (8) | 0.0020 (8) |
O1 | 0.0347 (9) | 0.0336 (9) | 0.0340 (8) | 0.0149 (7) | −0.0032 (7) | −0.0074 (7) |
C2 | 0.0344 (12) | 0.0373 (12) | 0.0269 (11) | 0.0101 (11) | 0.0039 (9) | −0.0005 (10) |
C3 | 0.0362 (12) | 0.0326 (13) | 0.0274 (11) | 0.0051 (10) | −0.0051 (9) | 0.0056 (9) |
C4 | 0.0252 (11) | 0.0242 (11) | 0.0292 (11) | 0.0018 (8) | −0.0053 (9) | −0.0040 (9) |
C5 | 0.0280 (11) | 0.0267 (11) | 0.0292 (11) | 0.0063 (9) | −0.0003 (9) | −0.0004 (9) |
C6 | 0.0244 (11) | 0.0261 (12) | 0.0315 (12) | 0.0041 (9) | −0.0040 (9) | 0.0005 (9) |
C7 | 0.0240 (11) | 0.0262 (11) | 0.0299 (12) | 0.0049 (9) | −0.0009 (9) | 0.0007 (9) |
C8 | 0.0283 (11) | 0.0231 (11) | 0.0296 (11) | 0.0008 (9) | −0.0017 (9) | −0.0010 (9) |
C9 | 0.0233 (11) | 0.0274 (11) | 0.0262 (11) | 0.0003 (9) | 0.0028 (9) | 0.0008 (9) |
C10 | 0.0299 (12) | 0.0244 (12) | 0.0314 (12) | 0.0061 (9) | −0.0059 (9) | −0.0027 (9) |
C11 | 0.0287 (11) | 0.0286 (11) | 0.0270 (10) | 0.0038 (9) | −0.0003 (9) | 0.0026 (9) |
C12 | 0.0244 (11) | 0.0228 (11) | 0.0263 (11) | 0.0012 (8) | −0.0009 (9) | 0.0008 (8) |
C13 | 0.0376 (13) | 0.0331 (12) | 0.0220 (11) | 0.0065 (10) | −0.0006 (9) | 0.0028 (9) |
C14 | 0.0263 (11) | 0.0330 (12) | 0.0292 (11) | 0.0010 (9) | 0.0004 (9) | −0.0016 (10) |
C1 | 0.0307 (12) | 0.0273 (11) | 0.0304 (11) | 0.0026 (9) | −0.0030 (9) | −0.0037 (10) |
Geometric parameters (Å, º) top
Mn1—O3W | 2.1412 (16) | N2—C7 | 1.417 (3) |
Mn1—O1i | 2.1517 (15) | O1—C1 | 1.287 (3) |
Mn1—O2W | 2.1547 (17) | O1—Mn1ii | 2.1517 (15) |
Mn1—O4 | 2.1648 (15) | C2—C13 | 1.363 (3) |
Mn1—O1W | 2.2209 (18) | C2—C5 | 1.391 (3) |
Mn1—O4W | 2.2262 (17) | C2—H2B | 0.9300 |
O1W—H1WA | 0.8486 | C3—C14 | 1.367 (3) |
O1W—H1WB | 0.8482 | C3—C10 | 1.400 (3) |
O2—C1 | 1.243 (3) | C3—H3B | 0.9300 |
O2W—H2WA | 0.8499 | C4—C11 | 1.388 (3) |
O2W—H2WB | 0.8498 | C4—C10 | 1.397 (3) |
O3—C5 | 1.357 (3) | C4—C1 | 1.498 (3) |
O3—H3A | 0.8200 | C5—C12 | 1.407 (3) |
O3W—H3WA | 0.8490 | C6—C11 | 1.384 (3) |
O3W—H3WB | 0.8486 | C6—C14 | 1.399 (3) |
O4—C8 | 1.277 (3) | C7—C9 | 1.388 (3) |
O4W—H4WA | 0.8500 | C7—C13 | 1.399 (3) |
O4W—H4WB | 0.8500 | C8—C12 | 1.497 (3) |
O5—C8 | 1.253 (3) | C9—C12 | 1.381 (3) |
O6—C10 | 1.353 (3) | C9—H9A | 0.9300 |
O6—H6A | 0.8200 | C11—H11A | 0.9300 |
N1—N2 | 1.259 (3) | C13—H13A | 0.9300 |
N1—C6 | 1.427 (3) | C14—H14A | 0.9300 |
| | | |
O3W—Mn1—O1i | 87.15 (6) | C10—C3—H3B | 119.8 |
O3W—Mn1—O2W | 91.58 (7) | C11—C4—C10 | 118.2 (2) |
O1i—Mn1—O2W | 106.40 (7) | C11—C4—C1 | 120.68 (19) |
O3W—Mn1—O4 | 173.45 (6) | C10—C4—C1 | 121.04 (19) |
O1i—Mn1—O4 | 86.77 (6) | O3—C5—C2 | 118.23 (19) |
O2W—Mn1—O4 | 87.81 (6) | O3—C5—C12 | 121.60 (19) |
O3W—Mn1—O1W | 86.88 (6) | C2—C5—C12 | 120.2 (2) |
O1i—Mn1—O1W | 164.63 (7) | C11—C6—C14 | 119.5 (2) |
O2W—Mn1—O1W | 87.92 (7) | C11—C6—N1 | 115.57 (19) |
O4—Mn1—O1W | 99.61 (6) | C14—C6—N1 | 124.8 (2) |
O3W—Mn1—O4W | 92.17 (7) | C9—C7—C13 | 119.0 (2) |
O1i—Mn1—O4W | 85.73 (7) | C9—C7—N2 | 125.02 (19) |
O2W—Mn1—O4W | 167.47 (7) | C13—C7—N2 | 116.00 (19) |
O4—Mn1—O4W | 89.80 (6) | O5—C8—O4 | 123.2 (2) |
O1W—Mn1—O4W | 80.36 (6) | O5—C8—C12 | 119.60 (19) |
Mn1—O1W—H1WA | 113.4 | O4—C8—C12 | 117.21 (19) |
Mn1—O1W—H1WB | 124.6 | C12—C9—C7 | 121.22 (19) |
H1WA—O1W—H1WB | 110.1 | C12—C9—H9A | 119.4 |
Mn1—O2W—H2WA | 134.4 | C7—C9—H9A | 119.4 |
Mn1—O2W—H2WB | 104.0 | O6—C10—C4 | 122.1 (2) |
H2WA—O2W—H2WB | 109.4 | O6—C10—C3 | 117.4 (2) |
C5—O3—H3A | 109.5 | C4—C10—C3 | 120.5 (2) |
Mn1—O3W—H3WA | 111.1 | C6—C11—C4 | 121.5 (2) |
Mn1—O3W—H3WB | 137.1 | C6—C11—H11A | 119.2 |
H3WA—O3W—H3WB | 110.0 | C4—C11—H11A | 119.2 |
C8—O4—Mn1 | 127.37 (14) | C9—C12—C5 | 118.70 (19) |
Mn1—O4W—H4WA | 109.5 | C9—C12—C8 | 119.74 (19) |
Mn1—O4W—H4WB | 118.9 | C5—C12—C8 | 121.57 (18) |
H4WA—O4W—H4WB | 109.3 | C2—C13—C7 | 120.8 (2) |
C10—O6—H6A | 109.5 | C2—C13—H13A | 119.6 |
N2—N1—C6 | 114.29 (18) | C7—C13—H13A | 119.6 |
N1—N2—C7 | 114.91 (18) | C3—C14—C6 | 119.9 (2) |
C1—O1—Mn1ii | 132.24 (14) | C3—C14—H14A | 120.1 |
C13—C2—C5 | 120.1 (2) | C6—C14—H14A | 120.1 |
C13—C2—H2B | 119.9 | O2—C1—O1 | 123.4 (2) |
C5—C2—H2B | 119.9 | O2—C1—C4 | 120.68 (19) |
C14—C3—C10 | 120.3 (2) | O1—C1—C4 | 115.89 (19) |
C14—C3—H3B | 119.8 | | |
Symmetry codes: (i) x−1, y+1, z; (ii) x+1, y−1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4W—H4WA···O3iii | 0.85 | 2.11 | 2.930 (3) | 162 |
O4W—H4WB···O5iv | 0.85 | 1.99 | 2.801 (2) | 160 |
O3W—H3WA···O2i | 0.85 | 1.95 | 2.729 (2) | 153 |
O3—H3A···O4 | 0.82 | 1.84 | 2.566 (2) | 147 |
O3W—H3WB···N1iv | 0.85 | 2.16 | 2.990 (3) | 166 |
O2W—H2WA···O2iv | 0.85 | 1.90 | 2.753 (3) | 176 |
O2W—H2WB···O5 | 0.85 | 2.13 | 2.846 (3) | 141 |
O6—H6A···O1 | 0.82 | 1.78 | 2.512 (2) | 147 |
O1W—H1WB···O5iv | 0.85 | 2.04 | 2.826 (3) | 153 |
O1W—H1WA···O6v | 0.85 | 2.32 | 2.907 (2) | 127 |
Symmetry codes: (i) x−1, y+1, z; (iii) −y+1, −x+1, −z+1/2; (iv) x−1/2, −y+3/2, −z+1/4; (v) −y+1/2, x−1/2, z−1/4. |