The title complex molecule, [Mn
2(C
7H
4ClO
2)
4(C
12H
8N
2)
2(H
2O)], possesses crystallographically imposed
C2 symmetry. Each Mn
II atom is coordinated by three carboxyl O atoms from three 4-chlorobenzoate ligands, two N atoms from one 1,10-phenanthroline ligand and one bridging water molecule in a distorted octahedral coordination geometry. The Mn
Mn separation is 3.512 (3) Å. Symmetrically related dinuclear molecules form chains parallel to the
c axis
via π–π stacking interactions.
Supporting information
CCDC reference: 647314
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.045
- wR factor = 0.122
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 - C4 .. 6.75 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C16
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24
Alert level G
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
4 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); 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, 1998); software used to prepare material for publication: SHELXTL.
µ-Aqua-bis(µ-4-chlorobenzoato)bis[(4-chlorobenzoato)(1,10-
phenanthroline)manganese(II)]
top
Crystal data top
[Mn2(C7H4ClO2)4(C12H8N2)2(H2O)] | F(000) = 2256 |
Mr = 1110.51 | Dx = 1.513 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2567 reflections |
a = 23.4037 (4) Å | θ = 2.1–27.0° |
b = 15.5866 (3) Å | µ = 0.80 mm−1 |
c = 15.5960 (3) Å | T = 293 K |
β = 121.012 (1)° | Block, yellow |
V = 4875.96 (16) Å3 | 0.30 × 0.25 × 0.18 mm |
Z = 4 | |
Data collection top
Bruker APEXII area-detector diffractometer | 4789 independent reflections |
Radiation source: fine-focus sealed tube | 3220 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
φ and ω scans | θmax = 26.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −28→28 |
Tmin = 0.796, Tmax = 0.870 | k = −18→19 |
16907 measured reflections | l = −18→19 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.049P)2 + 3.6113P] where P = (Fo2 + 2Fc2)/3 |
4789 reflections | (Δ/σ)max = 0.001 |
321 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.44 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 | 0.95729 (2) | 0.14240 (3) | 0.61870 (3) | 0.04110 (15) | |
Cl1 | 1.09812 (10) | 0.46735 (12) | 0.30516 (12) | 0.1513 (7) | |
Cl2 | 1.23754 (9) | −0.29182 (9) | 0.85550 (12) | 0.1410 (7) | |
O1 | 1.01247 (11) | 0.20592 (14) | 0.56182 (17) | 0.0590 (6) | |
O1W | 1.0000 | 0.23392 (18) | 0.7500 | 0.0459 (7) | |
H1W | 1.0169 | 0.2680 | 0.7269 | 0.069* | |
O2 | 1.03880 (12) | 0.32596 (15) | 0.65308 (17) | 0.0658 (6) | |
O3 | 1.02047 (10) | 0.03192 (13) | 0.66629 (15) | 0.0522 (5) | |
N1 | 0.88572 (12) | 0.06835 (16) | 0.47941 (17) | 0.0472 (6) | |
N2 | 0.86796 (12) | 0.23075 (17) | 0.52395 (18) | 0.0493 (6) | |
C1 | 0.89484 (17) | −0.0113 (2) | 0.4579 (2) | 0.0569 (8) | |
H1 | 0.9358 | −0.0375 | 0.4994 | 0.068* | |
C2 | 0.8458 (2) | −0.0575 (3) | 0.3758 (3) | 0.0725 (11) | |
H2 | 0.8538 | −0.1131 | 0.3630 | 0.087* | |
C3 | 0.7862 (2) | −0.0189 (3) | 0.3155 (3) | 0.0807 (13) | |
H3 | 0.7530 | −0.0485 | 0.2607 | 0.097* | |
C4 | 0.77390 (17) | 0.0654 (3) | 0.3347 (2) | 0.0649 (10) | |
C5 | 0.71301 (19) | 0.1104 (4) | 0.2739 (3) | 0.0842 (13) | |
H5 | 0.6782 | 0.0829 | 0.2187 | 0.101* | |
C6 | 0.70494 (18) | 0.1905 (4) | 0.2942 (3) | 0.0831 (13) | |
H6 | 0.6645 | 0.2178 | 0.2528 | 0.100* | |
C7 | 0.75674 (16) | 0.2363 (3) | 0.3783 (2) | 0.0637 (10) | |
C8 | 0.75078 (18) | 0.3214 (3) | 0.4032 (3) | 0.0732 (11) | |
H8 | 0.7116 | 0.3519 | 0.3636 | 0.088* | |
C9 | 0.80229 (18) | 0.3585 (3) | 0.4850 (3) | 0.0705 (10) | |
H9 | 0.7989 | 0.4149 | 0.5013 | 0.085* | |
C10 | 0.86019 (17) | 0.3121 (2) | 0.5445 (3) | 0.0585 (9) | |
H10 | 0.8950 | 0.3384 | 0.6008 | 0.070* | |
C11 | 0.81723 (14) | 0.1926 (2) | 0.4411 (2) | 0.0497 (8) | |
C12 | 0.82598 (15) | 0.1063 (2) | 0.4187 (2) | 0.0501 (8) | |
C13 | 1.03232 (14) | 0.2832 (2) | 0.5810 (2) | 0.0492 (8) | |
C14 | 1.04923 (15) | 0.3275 (2) | 0.5114 (2) | 0.0519 (8) | |
C15 | 1.0576 (2) | 0.2830 (3) | 0.4425 (3) | 0.0745 (11) | |
H15 | 1.0527 | 0.2237 | 0.4381 | 0.089* | |
C16 | 1.0735 (2) | 0.3265 (3) | 0.3790 (3) | 0.0977 (15) | |
H16 | 1.0795 | 0.2963 | 0.3328 | 0.117* | |
C17 | 1.0799 (2) | 0.4125 (3) | 0.3853 (3) | 0.0873 (13) | |
C18 | 1.0718 (2) | 0.4579 (3) | 0.4534 (3) | 0.0842 (12) | |
H18 | 1.0760 | 0.5173 | 0.4568 | 0.101* | |
C19 | 1.05719 (17) | 0.4147 (2) | 0.5169 (3) | 0.0654 (10) | |
H19 | 1.0527 | 0.4453 | 0.5642 | 0.079* | |
C20 | 1.07326 (14) | 0.0284 (2) | 0.7503 (2) | 0.0445 (7) | |
C21 | 1.11302 (15) | −0.05360 (19) | 0.7768 (2) | 0.0460 (7) | |
C22 | 1.09239 (18) | −0.1213 (2) | 0.7109 (3) | 0.0574 (9) | |
H22 | 1.0527 | −0.1174 | 0.6496 | 0.069* | |
C23 | 1.1304 (2) | −0.1947 (2) | 0.7354 (3) | 0.0768 (12) | |
H23 | 1.1163 | −0.2409 | 0.6915 | 0.092* | |
C24 | 1.1897 (2) | −0.1988 (3) | 0.8260 (4) | 0.0839 (13) | |
C25 | 1.2111 (2) | −0.1322 (3) | 0.8921 (3) | 0.0850 (13) | |
H25 | 1.2512 | −0.1356 | 0.9527 | 0.102* | |
C26 | 1.17241 (17) | −0.0603 (2) | 0.8678 (3) | 0.0644 (9) | |
H26 | 1.1861 | −0.0150 | 0.9130 | 0.077* | |
O4 | 1.09546 (10) | 0.08829 (13) | 0.81304 (16) | 0.0529 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Mn1 | 0.0380 (3) | 0.0427 (3) | 0.0369 (2) | 0.0001 (2) | 0.01527 (19) | 0.00160 (19) |
Cl1 | 0.2027 (17) | 0.1730 (15) | 0.1288 (12) | −0.0577 (13) | 0.1214 (12) | 0.0151 (11) |
Cl2 | 0.1960 (15) | 0.1122 (11) | 0.1676 (14) | 0.1030 (11) | 0.1313 (13) | 0.0775 (10) |
O1 | 0.0685 (15) | 0.0512 (15) | 0.0705 (15) | −0.0041 (12) | 0.0453 (13) | 0.0008 (11) |
O1W | 0.0498 (16) | 0.0467 (17) | 0.0422 (15) | 0.000 | 0.0243 (13) | 0.000 |
O2 | 0.0798 (16) | 0.0672 (16) | 0.0596 (15) | −0.0174 (13) | 0.0423 (13) | −0.0067 (12) |
O3 | 0.0462 (12) | 0.0527 (14) | 0.0488 (12) | 0.0076 (10) | 0.0181 (10) | 0.0013 (10) |
N1 | 0.0465 (15) | 0.0512 (17) | 0.0388 (13) | −0.0073 (12) | 0.0184 (12) | 0.0019 (11) |
N2 | 0.0420 (14) | 0.0559 (17) | 0.0465 (14) | 0.0017 (12) | 0.0204 (12) | 0.0108 (12) |
C1 | 0.063 (2) | 0.056 (2) | 0.0496 (18) | −0.0121 (17) | 0.0272 (16) | −0.0015 (16) |
C2 | 0.089 (3) | 0.069 (3) | 0.060 (2) | −0.033 (2) | 0.039 (2) | −0.0176 (19) |
C3 | 0.080 (3) | 0.103 (3) | 0.048 (2) | −0.049 (3) | 0.025 (2) | −0.014 (2) |
C4 | 0.056 (2) | 0.085 (3) | 0.0445 (18) | −0.024 (2) | 0.0192 (17) | 0.0022 (18) |
C5 | 0.051 (2) | 0.119 (4) | 0.048 (2) | −0.026 (3) | 0.0019 (18) | 0.011 (2) |
C6 | 0.040 (2) | 0.126 (4) | 0.058 (2) | 0.000 (2) | 0.0071 (18) | 0.029 (3) |
C7 | 0.0412 (18) | 0.093 (3) | 0.051 (2) | 0.0031 (19) | 0.0193 (16) | 0.0251 (19) |
C8 | 0.053 (2) | 0.091 (3) | 0.077 (3) | 0.027 (2) | 0.035 (2) | 0.040 (2) |
C9 | 0.063 (2) | 0.066 (2) | 0.085 (3) | 0.024 (2) | 0.040 (2) | 0.028 (2) |
C10 | 0.054 (2) | 0.054 (2) | 0.065 (2) | 0.0082 (17) | 0.0288 (17) | 0.0103 (17) |
C11 | 0.0376 (16) | 0.065 (2) | 0.0423 (17) | −0.0010 (15) | 0.0180 (14) | 0.0158 (15) |
C12 | 0.0430 (18) | 0.064 (2) | 0.0374 (15) | −0.0121 (16) | 0.0165 (14) | 0.0051 (15) |
C13 | 0.0367 (16) | 0.057 (2) | 0.0507 (18) | 0.0031 (15) | 0.0205 (14) | 0.0089 (16) |
C14 | 0.0438 (18) | 0.061 (2) | 0.0526 (19) | −0.0051 (15) | 0.0257 (15) | 0.0046 (15) |
C15 | 0.094 (3) | 0.070 (3) | 0.081 (3) | −0.016 (2) | 0.061 (2) | −0.007 (2) |
C16 | 0.124 (4) | 0.111 (4) | 0.096 (3) | −0.030 (3) | 0.084 (3) | −0.018 (3) |
C17 | 0.103 (3) | 0.097 (4) | 0.076 (3) | −0.023 (3) | 0.057 (3) | 0.013 (2) |
C18 | 0.102 (3) | 0.074 (3) | 0.087 (3) | −0.017 (2) | 0.056 (3) | 0.011 (2) |
C19 | 0.071 (2) | 0.062 (2) | 0.066 (2) | −0.0072 (19) | 0.0373 (19) | 0.0039 (18) |
C20 | 0.0398 (16) | 0.0492 (19) | 0.0480 (17) | −0.0013 (14) | 0.0251 (15) | 0.0014 (14) |
C21 | 0.0495 (18) | 0.0455 (18) | 0.0476 (17) | 0.0076 (14) | 0.0283 (15) | 0.0067 (14) |
C22 | 0.072 (2) | 0.048 (2) | 0.060 (2) | 0.0078 (17) | 0.0387 (18) | 0.0075 (16) |
C23 | 0.119 (4) | 0.048 (2) | 0.092 (3) | 0.012 (2) | 0.075 (3) | 0.007 (2) |
C24 | 0.107 (3) | 0.075 (3) | 0.098 (3) | 0.049 (3) | 0.073 (3) | 0.043 (3) |
C25 | 0.079 (3) | 0.097 (3) | 0.075 (3) | 0.041 (3) | 0.037 (2) | 0.035 (3) |
C26 | 0.063 (2) | 0.069 (2) | 0.056 (2) | 0.0129 (19) | 0.0269 (18) | 0.0080 (18) |
O4 | 0.0471 (12) | 0.0506 (13) | 0.0605 (13) | −0.0037 (10) | 0.0274 (11) | −0.0111 (11) |
Geometric parameters (Å, º) top
Mn1—O3 | 2.138 (2) | C8—C9 | 1.353 (5) |
Mn1—O1 | 2.148 (2) | C8—H8 | 0.9300 |
Mn1—O4i | 2.173 (2) | C9—C10 | 1.387 (5) |
Mn1—N1 | 2.260 (2) | C9—H9 | 0.9300 |
Mn1—O1W | 2.2624 (18) | C10—H10 | 0.9300 |
Mn1—N2 | 2.295 (2) | C11—C12 | 1.431 (5) |
Cl1—C17 | 1.739 (4) | C13—C14 | 1.502 (4) |
Cl2—C24 | 1.742 (4) | C14—C19 | 1.369 (5) |
O1—C13 | 1.270 (4) | C14—C15 | 1.375 (5) |
O1W—Mn1i | 2.2623 (18) | C15—C16 | 1.400 (5) |
O1W—H1W | 0.8456 | C15—H15 | 0.9300 |
O2—C13 | 1.247 (4) | C16—C17 | 1.346 (6) |
O3—C20 | 1.256 (3) | C16—H16 | 0.9300 |
N1—C1 | 1.331 (4) | C17—C18 | 1.369 (6) |
N1—C12 | 1.355 (4) | C18—C19 | 1.377 (5) |
N2—C10 | 1.343 (4) | C18—H18 | 0.9300 |
N2—C11 | 1.360 (4) | C19—H19 | 0.9300 |
C1—C2 | 1.400 (5) | C20—O4 | 1.256 (3) |
C1—H1 | 0.9300 | C20—C21 | 1.507 (4) |
C2—C3 | 1.356 (6) | C21—C22 | 1.375 (4) |
C2—H2 | 0.9300 | C21—C26 | 1.387 (4) |
C3—C4 | 1.410 (6) | C22—C23 | 1.378 (5) |
C3—H3 | 0.9300 | C22—H22 | 0.9300 |
C4—C12 | 1.401 (4) | C23—C24 | 1.381 (6) |
C4—C5 | 1.424 (6) | C23—H23 | 0.9300 |
C5—C6 | 1.326 (6) | C24—C25 | 1.364 (6) |
C5—H5 | 0.9300 | C25—C26 | 1.365 (5) |
C6—C7 | 1.435 (5) | C25—H25 | 0.9300 |
C6—H6 | 0.9300 | C26—H26 | 0.9300 |
C7—C8 | 1.409 (5) | O4—Mn1i | 2.173 (2) |
C7—C11 | 1.413 (4) | | |
| | | |
O3—Mn1—O1 | 93.40 (8) | N2—C10—C9 | 122.6 (3) |
O3—Mn1—O4i | 89.04 (8) | N2—C10—H10 | 118.7 |
O1—Mn1—O4i | 174.36 (9) | C9—C10—H10 | 118.7 |
O3—Mn1—N1 | 87.70 (9) | N2—C11—C7 | 121.4 (3) |
O1—Mn1—N1 | 98.28 (9) | N2—C11—C12 | 118.5 (3) |
O4i—Mn1—N1 | 86.90 (8) | C7—C11—C12 | 120.1 (3) |
O3—Mn1—O1W | 106.84 (7) | N1—C12—C4 | 122.8 (3) |
O1—Mn1—O1W | 90.22 (7) | N1—C12—C11 | 117.8 (3) |
O4i—Mn1—O1W | 84.19 (7) | C4—C12—C11 | 119.4 (3) |
N1—Mn1—O1W | 162.76 (7) | O2—C13—O1 | 125.4 (3) |
O3—Mn1—N2 | 160.80 (9) | O2—C13—C14 | 116.8 (3) |
O1—Mn1—N2 | 89.97 (9) | O1—C13—C14 | 117.8 (3) |
O4i—Mn1—N2 | 89.38 (8) | C19—C14—C15 | 118.7 (3) |
N1—Mn1—N2 | 73.11 (9) | C19—C14—C13 | 119.3 (3) |
O1W—Mn1—N2 | 92.03 (8) | C15—C14—C13 | 122.0 (3) |
C13—O1—Mn1 | 124.4 (2) | C14—C15—C16 | 120.3 (4) |
Mn1—O1W—Mn1i | 101.82 (11) | C14—C15—H15 | 119.8 |
Mn1—O1W—H1W | 95.5 | C16—C15—H15 | 119.8 |
Mn1i—O1W—H1W | 134.1 | C17—C16—C15 | 119.5 (4) |
C20—O3—Mn1 | 122.0 (2) | C17—C16—H16 | 120.3 |
C1—N1—C12 | 118.2 (3) | C15—C16—H16 | 120.3 |
C1—N1—Mn1 | 125.6 (2) | C16—C17—C18 | 121.0 (4) |
C12—N1—Mn1 | 115.8 (2) | C16—C17—Cl1 | 119.8 (4) |
C10—N2—C11 | 118.7 (3) | C18—C17—Cl1 | 119.1 (4) |
C10—N2—Mn1 | 127.1 (2) | C17—C18—C19 | 119.3 (4) |
C11—N2—Mn1 | 114.1 (2) | C17—C18—H18 | 120.3 |
N1—C1—C2 | 123.2 (3) | C19—C18—H18 | 120.3 |
N1—C1—H1 | 118.4 | C14—C19—C18 | 121.1 (4) |
C2—C1—H1 | 118.4 | C14—C19—H19 | 119.4 |
C3—C2—C1 | 118.2 (4) | C18—C19—H19 | 119.4 |
C3—C2—H2 | 120.9 | O4—C20—O3 | 124.7 (3) |
C1—C2—H2 | 120.9 | O4—C20—C21 | 117.9 (3) |
C2—C3—C4 | 121.0 (3) | O3—C20—C21 | 117.4 (3) |
C2—C3—H3 | 119.5 | C22—C21—C26 | 119.2 (3) |
C4—C3—H3 | 119.5 | C22—C21—C20 | 121.0 (3) |
C12—C4—C3 | 116.6 (3) | C26—C21—C20 | 119.7 (3) |
C12—C4—C5 | 119.3 (4) | C21—C22—C23 | 120.1 (3) |
C3—C4—C5 | 124.1 (4) | C21—C22—H22 | 119.9 |
C6—C5—C4 | 121.4 (4) | C23—C22—H22 | 119.9 |
C6—C5—H5 | 119.3 | C22—C23—C24 | 119.2 (4) |
C4—C5—H5 | 119.3 | C22—C23—H23 | 120.4 |
C5—C6—C7 | 122.0 (4) | C24—C23—H23 | 120.4 |
C5—C6—H6 | 119.0 | C25—C24—C23 | 121.5 (4) |
C7—C6—H6 | 119.0 | C25—C24—Cl2 | 120.0 (4) |
C8—C7—C11 | 117.9 (3) | C23—C24—Cl2 | 118.6 (4) |
C8—C7—C6 | 124.3 (4) | C24—C25—C26 | 118.9 (4) |
C11—C7—C6 | 117.8 (4) | C24—C25—H25 | 120.6 |
C9—C8—C7 | 119.7 (3) | C26—C25—H25 | 120.6 |
C9—C8—H8 | 120.1 | C25—C26—C21 | 121.1 (4) |
C7—C8—H8 | 120.1 | C25—C26—H26 | 119.5 |
C8—C9—C10 | 119.8 (4) | C21—C26—H26 | 119.5 |
C8—C9—H9 | 120.1 | C20—O4—Mn1i | 124.00 (18) |
C10—C9—H9 | 120.1 | | |
Symmetry code: (i) −x+2, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O2 | 0.85 | 1.74 | 2.565 (3) | 167 |
C1—H1···O3 | 0.93 | 2.56 | 3.133 (3) | 120 |
C8—H8···O4ii | 0.93 | 2.58 | 3.450 (5) | 156 |
Symmetry code: (ii) x−1/2, −y+1/2, z−1/2. |