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The asymmetric unit of the title compound, (C
7H
7N
2)
2[Mn(C
7H
3O
4N)
2(H
2O)
2]·2H
2O, contains one half-anion, one cation and one uncoordinated water molecule. The Mn
II atom, lying on a centre of symmetry, is coordinated in a distorted octahedral arrangement by two O atoms and two N atoms of two pyridine-2,4-dicarboxylate and two O atoms of two aqua ligands. In the crystal structure, intermolecular O—H
O and N—H
O hydrogen bonds and π–π interactions link the molecules into a three-dimensional supramolecular framework.
Supporting information
CCDC reference: 647236
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.051
- wR factor = 0.129
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3
H2 O
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
Bis(benzimidazolium)
diaquabis(pyridine-2,4-dicarboxylato-
κ2N,
O)manganese(II)
dihydrate
top
Crystal data top
(C7H7N2)2[Mn(C7H3O4N)2(H2O)2]·2H2O | Z = 1 |
Mr = 695.50 | F(000) = 359 |
Triclinic, P1 | Dx = 1.558 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4882 (18) Å | Cell parameters from 1565 reflections |
b = 9.0617 (19) Å | θ = 2.8–27.5° |
c = 10.7716 (19) Å | µ = 0.52 mm−1 |
α = 96.539 (6)° | T = 294 K |
β = 101.032 (6)° | Prism, yellow |
γ = 111.508 (5)° | 0.25 × 0.20 × 0.10 mm |
V = 741.1 (3) Å3 | |
Data collection top
Bruker P4 diffractometer | 3336 independent reflections |
Radiation source: fine-focus sealed tube | 2518 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ω scans | θmax = 27.5°, θmin = 2.8° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.882, Tmax = 0.949 | k = −11→10 |
5758 measured reflections | l = −13→13 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0612P)2 + 0.2861P] where P = (Fo2 + 2Fc2)/3 |
3336 reflections | (Δ/σ)max < 0.001 |
230 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
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 | 0.5000 | 0.5000 | 1.0000 | 0.03100 (18) | |
N1 | 0.2762 (3) | 0.5338 (3) | 0.87778 (19) | 0.0293 (5) | |
N2 | 0.5380 (3) | 0.7591 (3) | 0.5869 (2) | 0.0358 (5) | |
H2A | 0.6166 | 0.7396 | 0.6371 | 0.043* | |
N3 | 0.3660 (3) | 0.7646 (3) | 0.4112 (2) | 0.0340 (5) | |
H1A | 0.3167 | 0.7499 | 0.3306 | 0.041* | |
C1 | 0.2079 (4) | 0.9105 (4) | 0.5182 (3) | 0.0424 (7) | |
H1B | 0.1319 | 0.9113 | 0.4439 | 0.051* | |
C2 | 0.3267 (3) | 0.8397 (3) | 0.5131 (2) | 0.0298 (5) | |
C3 | 0.4381 (3) | 0.8372 (3) | 0.6256 (3) | 0.0310 (6) | |
C4 | 0.4359 (4) | 0.9056 (4) | 0.7470 (3) | 0.0410 (7) | |
H4A | 0.5096 | 0.9034 | 0.8221 | 0.049* | |
C5 | 0.3180 (5) | 0.9770 (4) | 0.7498 (3) | 0.0499 (8) | |
H5A | 0.3124 | 1.0249 | 0.8290 | 0.060* | |
C6 | 0.2083 (4) | 0.9793 (4) | 0.6384 (4) | 0.0531 (9) | |
H6A | 0.1314 | 1.0294 | 0.6450 | 0.064* | |
C7 | 0.4923 (4) | 0.7194 (3) | 0.4593 (3) | 0.0383 (6) | |
H7A | 0.5424 | 0.6668 | 0.4101 | 0.046* | |
C8 | 0.0067 (3) | 0.6130 (3) | 0.7543 (2) | 0.0270 (5) | |
C9 | 0.0775 (3) | 0.6628 (3) | 0.8871 (2) | 0.0276 (5) | |
H9A | 0.0356 | 0.7240 | 0.9364 | 0.033* | |
C10 | 0.2101 (3) | 0.6208 (3) | 0.9453 (2) | 0.0259 (5) | |
C11 | 0.2063 (4) | 0.4837 (3) | 0.7502 (2) | 0.0338 (6) | |
H11A | 0.2502 | 0.4227 | 0.7028 | 0.041* | |
C12 | 0.0712 (4) | 0.5196 (3) | 0.6867 (2) | 0.0331 (6) | |
H12A | 0.0240 | 0.4807 | 0.5983 | 0.040* | |
C13 | 0.2878 (3) | 0.6649 (3) | 1.0904 (2) | 0.0274 (5) | |
C14 | −0.1358 (3) | 0.6591 (3) | 0.6849 (2) | 0.0309 (6) | |
O1 | −0.1882 (3) | 0.7465 (2) | 0.75482 (18) | 0.0386 (5) | |
O2 | −0.1924 (3) | 0.6113 (3) | 0.56707 (18) | 0.0461 (5) | |
O3 | 0.2246 (2) | 0.7398 (2) | 1.15757 (16) | 0.0360 (5) | |
O4 | 0.4100 (2) | 0.6229 (2) | 1.13554 (16) | 0.0342 (4) | |
O5 | 0.6890 (3) | 0.7362 (3) | 0.9736 (2) | 0.0399 (5) | |
H5C | 0.732 (5) | 0.733 (4) | 0.901 (4) | 0.070 (12)* | |
H5B | 0.785 (6) | 0.781 (5) | 1.035 (4) | 0.071 (13)* | |
O6 | 1.0010 (3) | 0.9022 (3) | 1.1599 (3) | 0.0575 (7) | |
H6B | 1.070 (7) | 0.871 (6) | 1.159 (5) | 0.103 (18)* | |
H6C | 1.053 (6) | 1.011 (6) | 1.174 (4) | 0.094 (16)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Mn1 | 0.0293 (3) | 0.0426 (4) | 0.0278 (3) | 0.0237 (3) | 0.0045 (2) | 0.0056 (2) |
N1 | 0.0285 (11) | 0.0407 (12) | 0.0238 (11) | 0.0203 (10) | 0.0059 (9) | 0.0051 (9) |
N2 | 0.0320 (12) | 0.0441 (14) | 0.0362 (13) | 0.0218 (11) | 0.0046 (10) | 0.0105 (10) |
N3 | 0.0343 (12) | 0.0412 (13) | 0.0252 (11) | 0.0167 (10) | 0.0034 (9) | 0.0028 (9) |
C1 | 0.0342 (16) | 0.0508 (18) | 0.0482 (17) | 0.0234 (14) | 0.0074 (13) | 0.0158 (14) |
C2 | 0.0260 (13) | 0.0319 (13) | 0.0301 (13) | 0.0104 (11) | 0.0051 (10) | 0.0078 (11) |
C3 | 0.0272 (13) | 0.0354 (14) | 0.0317 (14) | 0.0130 (11) | 0.0077 (11) | 0.0097 (11) |
C4 | 0.0431 (17) | 0.0429 (17) | 0.0311 (15) | 0.0106 (13) | 0.0094 (13) | 0.0065 (12) |
C5 | 0.058 (2) | 0.0451 (18) | 0.0482 (19) | 0.0174 (16) | 0.0288 (17) | 0.0021 (14) |
C6 | 0.050 (2) | 0.054 (2) | 0.071 (2) | 0.0319 (17) | 0.0258 (18) | 0.0146 (17) |
C7 | 0.0374 (16) | 0.0406 (16) | 0.0418 (16) | 0.0202 (13) | 0.0135 (13) | 0.0050 (13) |
C8 | 0.0244 (12) | 0.0296 (13) | 0.0272 (13) | 0.0124 (10) | 0.0038 (10) | 0.0056 (10) |
C9 | 0.0279 (13) | 0.0353 (14) | 0.0241 (12) | 0.0180 (11) | 0.0065 (10) | 0.0048 (10) |
C10 | 0.0248 (12) | 0.0325 (13) | 0.0223 (12) | 0.0139 (11) | 0.0051 (10) | 0.0060 (10) |
C11 | 0.0401 (15) | 0.0441 (16) | 0.0241 (13) | 0.0262 (13) | 0.0076 (11) | 0.0020 (11) |
C12 | 0.0361 (15) | 0.0459 (16) | 0.0202 (12) | 0.0223 (13) | 0.0039 (11) | 0.0036 (11) |
C13 | 0.0272 (13) | 0.0321 (13) | 0.0247 (12) | 0.0150 (11) | 0.0048 (10) | 0.0043 (10) |
C14 | 0.0306 (14) | 0.0341 (14) | 0.0314 (14) | 0.0167 (11) | 0.0056 (11) | 0.0105 (11) |
O1 | 0.0389 (11) | 0.0543 (13) | 0.0338 (10) | 0.0313 (10) | 0.0075 (9) | 0.0107 (9) |
O2 | 0.0482 (13) | 0.0622 (14) | 0.0292 (11) | 0.0328 (11) | −0.0056 (9) | 0.0029 (9) |
O3 | 0.0395 (11) | 0.0493 (12) | 0.0253 (9) | 0.0283 (10) | 0.0055 (8) | −0.0012 (8) |
O4 | 0.0344 (10) | 0.0483 (11) | 0.0241 (9) | 0.0260 (9) | 0.0005 (8) | 0.0027 (8) |
O5 | 0.0363 (12) | 0.0458 (12) | 0.0395 (12) | 0.0172 (10) | 0.0124 (10) | 0.0087 (10) |
O6 | 0.0433 (14) | 0.0534 (16) | 0.0750 (17) | 0.0267 (13) | 0.0085 (12) | −0.0057 (13) |
Geometric parameters (Å, º) top
Mn1—O4i | 2.1534 (17) | C5—C6 | 1.379 (5) |
Mn1—O4 | 2.1534 (17) | C5—H5A | 0.9300 |
Mn1—N1i | 2.235 (2) | C6—H6A | 0.9300 |
Mn1—N1 | 2.235 (2) | C7—H7A | 0.9300 |
Mn1—O5i | 2.243 (2) | C8—C12 | 1.378 (3) |
Mn1—O5 | 2.243 (2) | C8—C9 | 1.392 (3) |
N1—C11 | 1.339 (3) | C8—C14 | 1.514 (3) |
N1—C10 | 1.348 (3) | C9—C10 | 1.380 (3) |
N2—C7 | 1.323 (4) | C9—H9A | 0.9300 |
N2—C3 | 1.379 (3) | C10—C13 | 1.519 (3) |
N2—H2A | 0.8600 | C11—C12 | 1.383 (3) |
N3—C7 | 1.321 (3) | C11—H11A | 0.9300 |
N3—C2 | 1.384 (3) | C12—H12A | 0.9300 |
N3—H1A | 0.8600 | C13—O3 | 1.255 (3) |
C1—C6 | 1.370 (5) | C13—O4 | 1.263 (3) |
C1—C2 | 1.385 (3) | C14—O2 | 1.232 (3) |
C1—H1B | 0.9300 | C14—O1 | 1.281 (3) |
C2—C3 | 1.395 (4) | O5—H5C | 0.93 (4) |
C3—C4 | 1.389 (4) | O5—H5B | 0.87 (4) |
C4—C5 | 1.379 (4) | O6—H6B | 0.74 (5) |
C4—H4A | 0.9300 | O6—H6C | 0.90 (5) |
| | | |
O4i—Mn1—O4 | 180.00 (7) | C4—C5—H5A | 119.1 |
O4i—Mn1—N1i | 75.73 (7) | C1—C6—C5 | 122.6 (3) |
O4—Mn1—N1i | 104.27 (7) | C1—C6—H6A | 118.7 |
O4i—Mn1—N1 | 104.27 (7) | C5—C6—H6A | 118.7 |
O4—Mn1—N1 | 75.73 (7) | N3—C7—N2 | 110.8 (2) |
N1i—Mn1—N1 | 180.000 (1) | N3—C7—H7A | 124.6 |
O4i—Mn1—O5i | 91.45 (8) | N2—C7—H7A | 124.6 |
O4—Mn1—O5i | 88.55 (8) | C12—C8—C9 | 117.7 (2) |
N1i—Mn1—O5i | 90.88 (8) | C12—C8—C14 | 120.5 (2) |
N1—Mn1—O5i | 89.12 (8) | C9—C8—C14 | 121.8 (2) |
O4i—Mn1—O5 | 88.55 (8) | C10—C9—C8 | 119.6 (2) |
O4—Mn1—O5 | 91.45 (8) | C10—C9—H9A | 120.2 |
N1i—Mn1—O5 | 89.12 (8) | C8—C9—H9A | 120.2 |
N1—Mn1—O5 | 90.88 (8) | N1—C10—C9 | 122.3 (2) |
O5i—Mn1—O5 | 180.0 | N1—C10—C13 | 115.35 (19) |
C11—N1—C10 | 118.1 (2) | C9—C10—C13 | 122.3 (2) |
C11—N1—Mn1 | 128.86 (16) | N1—C11—C12 | 122.3 (2) |
C10—N1—Mn1 | 113.01 (15) | N1—C11—H11A | 118.8 |
C7—N2—C3 | 108.3 (2) | C12—C11—H11A | 118.8 |
C7—N2—O1ii | 129.05 (17) | C8—C12—C11 | 120.0 (2) |
C3—N2—O1ii | 121.83 (17) | C8—C12—H12A | 120.0 |
C7—N2—H2A | 125.8 | C11—C12—H12A | 120.0 |
C3—N2—H2A | 125.8 | O3—C13—O4 | 124.4 (2) |
C7—N3—C2 | 108.0 (2) | O3—C13—C10 | 117.4 (2) |
C7—N3—O3iii | 126.61 (18) | O4—C13—C10 | 118.2 (2) |
C2—N3—O3iii | 125.17 (16) | O2—C14—O1 | 124.9 (2) |
C7—N3—H1A | 126.0 | O2—C14—C8 | 118.5 (2) |
C2—N3—H1A | 126.0 | O1—C14—C8 | 116.6 (2) |
C6—C1—C2 | 116.5 (3) | C13—O4—Mn1 | 117.45 (15) |
C6—C1—H1B | 121.7 | Mn1—O5—O1ii | 119.38 (10) |
C2—C1—H1B | 121.7 | Mn1—O5—O6 | 119.15 (11) |
N3—C2—C1 | 132.4 (2) | O1ii—O5—O6 | 99.95 (10) |
N3—C2—C3 | 106.5 (2) | Mn1—O5—H5C | 117 (2) |
C1—C2—C3 | 121.1 (2) | O6—O5—H5C | 99 (2) |
N2—C3—C4 | 131.8 (3) | Mn1—O5—H5B | 115 (3) |
N2—C3—C2 | 106.3 (2) | O1ii—O5—H5B | 102 (3) |
C4—C3—C2 | 121.9 (2) | H5C—O5—H5B | 102 (3) |
C5—C4—C3 | 116.1 (3) | O3ii—O6—O1iv | 113.10 (10) |
C5—C4—H4A | 122.0 | O1iv—O6—H6B | 105 (4) |
C3—C4—H4A | 122.0 | O3ii—O6—H6C | 116 (3) |
C6—C5—C4 | 121.8 (3) | H6B—O6—H6C | 107 (5) |
C6—C5—H5A | 119.1 | | |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x+1, y, z; (iii) x, y, z−1; (iv) −x+1, −y+2, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1ii | 0.86 | 1.86 | 2.705 (3) | 167 |
N3—H1A···O3iii | 0.86 | 1.86 | 2.713 (3) | 174 |
O5—H5C···O1ii | 0.93 (4) | 1.83 (4) | 2.751 (3) | 174 (3) |
O5—H5B···O6 | 0.87 (4) | 1.90 (4) | 2.767 (4) | 173 (4) |
O6—H6B···O3ii | 0.74 (5) | 2.07 (5) | 2.797 (3) | 169 (5) |
O6—H6C···O1iv | 0.90 (5) | 2.04 (5) | 2.927 (4) | 168 (4) |
Symmetry codes: (ii) x+1, y, z; (iii) x, y, z−1; (iv) −x+1, −y+2, −z+2. |
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