Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051628/bg2114sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051628/bg2114Isup2.hkl |
CCDC reference: 667219
To a solution of 2,9-dimethyl-1,10-phenanthroline (C14H12N2.0.5H2O, 0.1089 g, 0.5 mmol), 3-hydroxy-benzoate (0.0693 g, 0.5 mmol) and sodium hydroxide (0.01979 g,0.5 mmol) in ethanol/water (v:v=1:1, 5 ml) was added a solution of 50% Mn(NO3)2(0.2016 g, 0.5 mmol) in distilled water (5 ml). The resulting solution was stirred for 3 h at 323 K and filtered. Yellow single crystals of (I) were obtained by slow evaporation of the filtrate over 30 days.
The H atoms bound to O were found via Fourier difference map,and refined as riding in their as-found relative positions with Uiso(H) = 1.5Ueq(O). Other H atoms were positioned geometrically and refined using a riding model, with fixed C—H distances of 0.93 Å (C—H) [Uiso(H) = 1.2Ueq(C)] and 0.96 Å (CH3) [Uiso(H) = 1.5Ueq(C)].
Crystal structures of metal complexes of 1,10-phenanthroline or its derivatives combinated with benzoic anions have been reported (Fu et al., 2006; Liu & Ng, 2007; Niu et al., 2002; Pan, Liu et al., 2006; Pan, Su et al., 2006a,b; Shi et al., 2001; Su, Gu et al., 2005a,b; Su & Xu, 2005; Su, Zhang & Xu,2005; Xu et al., 2004). Recently, as part of our ongoing studies (Xuan, Zhao & Tang, 2007; Xuan, Zhao & Zhang, 2007); Zhao, Xuan & Wang, 2007; Zhao, Yan et al., 2007) of mixed-ligand complexes, we have reported the structure of bis(benzoato-κ2O,O')(2,9-dimethyl-1,10-phenanthroline-κ2N,N') manganese(II) (Zhao, Xuan et al., 2007). In this paper, we present the crystal structure of the manganese complex of dmphen and 3-hydroxy-benzoate anion, [Mn(C7H5O3)2(C14H12N2)]. (C14H12N2).2H2O, (I) which was obtained by reaction of dmphen, sodium 3-hydroxy-benzoate and Mn(NO3)2 aqueous solutions.
As shown in Fig. 1, the structure unit of (I) is composed of a MnII complex, [Mn(C7H5O3)2(C14H12N2)], one non-coordinated dmphen molecule and two crystal water molecules. Two N atoms of one dmphen ligand and four O atoms of two 3-hydroxy-benzoate anions are coordinated to the MnII ion in a strongly distorted octahedral arrangement. The corresponding bond lengths are listed in Table 1.
The crystal structure of (I) is stabilized by a profuse network of O—H···O and O—H···N hydrogen bonds having water molecules and the 3-hydroxy-benzoate anion as donors and the same groups plus the non-coordinated dmphen molecule as acceptors (Table 2 and Fig. 2).
The closely related complex bis(benzoato-κ2O,O')(2,9-dimethyl-1,10-phenanthroline-κ2N,N')manganese(II) was reported by Zhao, Xuan et al., (2007). For other related structures, see: Fu et al. (2006); Liu & Ng (2007); Niu et al., (2002); Pan, Liu et al. (2006); Pan, Su et al. (2006a,b); Shi et al. (2001); Su, Gu et al. (2005a, b); Su & Xu (2005); Su, Zhang & Xu (2005); Xu et al. (2004); Xuan, Zhao & Tang (2007); Xuan, Zhao & Zhang (2007); Zhao, Yan et al. (2007); Zhao, Xuan et al. (2007).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXTL (Sheldrick, 1990).
[Mn(C7H5O3)2(C14H12N2)]·C14H12N2·2H2O | F(000) = 1628 |
Mr = 781.70 | Dx = 1.349 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5503 reflections |
a = 10.7010 (9) Å | θ = 2.4–22.2° |
b = 24.865 (2) Å | µ = 0.40 mm−1 |
c = 14.5083 (12) Å | T = 291 K |
β = 94.514 (1)° | Block, yellow |
V = 3848.5 (5) Å3 | 0.34 × 0.25 × 0.24 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 7162 independent reflections |
Radiation source: fine-focus sealed tube | 5040 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
φ and ω scans | θmax = 25.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS in SAINT; Bruker, 1997) | h = −12→12 |
Tmin = 0.876, Tmax = 0.910 | k = −30→30 |
26490 measured reflections | l = −17→17 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0901P)2 + 1.8289P] where P = (Fo2 + 2Fc2)/3 |
7162 reflections | (Δ/σ)max = 0.001 |
502 parameters | Δρmax = 0.87 e Å−3 |
18 restraints | Δρmin = −0.37 e Å−3 |
[Mn(C7H5O3)2(C14H12N2)]·C14H12N2·2H2O | V = 3848.5 (5) Å3 |
Mr = 781.70 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.7010 (9) Å | µ = 0.40 mm−1 |
b = 24.865 (2) Å | T = 291 K |
c = 14.5083 (12) Å | 0.34 × 0.25 × 0.24 mm |
β = 94.514 (1)° |
Bruker SMART CCD area-detector diffractometer | 7162 independent reflections |
Absorption correction: multi-scan (SADABS in SAINT; Bruker, 1997) | 5040 reflections with I > 2σ(I) |
Tmin = 0.876, Tmax = 0.910 | Rint = 0.031 |
26490 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 18 restraints |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.87 e Å−3 |
7162 reflections | Δρmin = −0.37 e Å−3 |
502 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Mn1 | 0.00824 (4) | 0.244319 (18) | 0.09991 (3) | 0.04685 (17) | |
O1 | 0.0685 (2) | 0.16091 (9) | 0.07514 (16) | 0.0633 (6) | |
O2 | −0.0670 (2) | 0.17259 (9) | 0.17687 (16) | 0.0612 (6) | |
O3 | −0.1536 (4) | −0.01844 (12) | 0.2890 (3) | 0.1281 (14) | |
H3 | −0.1653 | 0.0020 | 0.3318 | 0.192* | |
O4 | −0.0488 (2) | 0.30156 (10) | 0.21655 (15) | 0.0644 (6) | |
O5 | 0.1445 (2) | 0.27461 (10) | 0.20459 (15) | 0.0639 (6) | |
O6 | −0.0292 (3) | 0.39008 (14) | 0.53298 (18) | 0.0950 (9) | |
H6 | −0.1002 | 0.3850 | 0.5091 | 0.143* | |
N1 | −0.1434 (2) | 0.27463 (9) | 0.00078 (16) | 0.0431 (5) | |
N2 | 0.1071 (2) | 0.27329 (10) | −0.02296 (16) | 0.0471 (6) | |
N3 | 0.1062 (3) | 0.46939 (12) | 0.8100 (3) | 0.0790 (9) | |
N4 | 0.2962 (3) | 0.43994 (12) | 0.9354 (2) | 0.0705 (8) | |
C1 | −0.3072 (3) | 0.25456 (15) | 0.1030 (3) | 0.0633 (9) | |
H1A | −0.3388 | 0.2187 | 0.0932 | 0.095* | |
H1B | −0.3721 | 0.2771 | 0.1239 | 0.095* | |
H1C | −0.2375 | 0.2539 | 0.1489 | 0.095* | |
C2 | −0.2657 (3) | 0.27613 (12) | 0.0151 (2) | 0.0494 (7) | |
C3 | −0.3528 (3) | 0.29696 (14) | −0.0524 (2) | 0.0616 (9) | |
H3A | −0.4371 | 0.2984 | −0.0410 | 0.074* | |
C4 | −0.3167 (3) | 0.31506 (14) | −0.1338 (3) | 0.0634 (9) | |
H4 | −0.3760 | 0.3282 | −0.1785 | 0.076* | |
C5 | −0.1884 (3) | 0.31413 (12) | −0.1510 (2) | 0.0535 (8) | |
C6 | −0.1424 (4) | 0.33335 (14) | −0.2343 (2) | 0.0651 (9) | |
H6A | −0.1987 | 0.3461 | −0.2814 | 0.078* | |
C7 | −0.0209 (4) | 0.33350 (14) | −0.2459 (2) | 0.0672 (10) | |
H7 | 0.0067 | 0.3467 | −0.3008 | 0.081* | |
C8 | 0.0693 (3) | 0.31352 (13) | −0.1751 (2) | 0.0561 (8) | |
C9 | 0.1994 (4) | 0.31283 (15) | −0.1838 (2) | 0.0655 (9) | |
H9 | 0.2317 | 0.3269 | −0.2363 | 0.079* | |
C10 | 0.2770 (3) | 0.29172 (16) | −0.1155 (3) | 0.0684 (10) | |
H10 | 0.3626 | 0.2900 | −0.1223 | 0.082* | |
C11 | 0.2295 (3) | 0.27208 (14) | −0.0335 (2) | 0.0551 (8) | |
C12 | 0.3154 (3) | 0.25003 (16) | 0.0437 (3) | 0.0698 (10) | |
H12A | 0.3482 | 0.2790 | 0.0820 | 0.105* | |
H12B | 0.3833 | 0.2312 | 0.0186 | 0.105* | |
H12C | 0.2698 | 0.2257 | 0.0801 | 0.105* | |
C13 | 0.0274 (3) | 0.29343 (11) | −0.09279 (19) | 0.0456 (7) | |
C14 | −0.1051 (3) | 0.29368 (11) | −0.08021 (19) | 0.0442 (7) | |
C15 | −0.0003 (3) | 0.14134 (13) | 0.1343 (2) | 0.0496 (7) | |
C16 | 0.0001 (3) | 0.08214 (12) | 0.1523 (2) | 0.0521 (7) | |
C17 | 0.0791 (4) | 0.04892 (15) | 0.1076 (3) | 0.0736 (10) | |
H17 | 0.1321 | 0.0633 | 0.0662 | 0.088* | |
C18 | 0.0792 (4) | −0.00595 (16) | 0.1247 (3) | 0.0868 (12) | |
H18 | 0.1325 | −0.0283 | 0.0946 | 0.104* | |
C19 | 0.0016 (4) | −0.02744 (15) | 0.1854 (3) | 0.0847 (12) | |
H19 | 0.0021 | −0.0643 | 0.1961 | 0.102* | |
C20 | −0.0777 (4) | 0.00548 (15) | 0.2310 (3) | 0.0832 (12) | |
C21 | −0.0775 (4) | 0.06064 (14) | 0.2143 (2) | 0.0679 (10) | |
H21 | −0.1299 | 0.0831 | 0.2451 | 0.081* | |
C22 | 0.0647 (3) | 0.29992 (12) | 0.2478 (2) | 0.0533 (8) | |
C23 | 0.1069 (3) | 0.32856 (12) | 0.3350 (2) | 0.0518 (7) | |
C24 | 0.0192 (3) | 0.34615 (13) | 0.3921 (2) | 0.0588 (8) | |
H24 | −0.0655 | 0.3405 | 0.3757 | 0.071* | |
C25 | 0.0564 (4) | 0.37238 (14) | 0.4747 (2) | 0.0696 (10) | |
C26 | 0.1824 (5) | 0.38026 (16) | 0.4978 (3) | 0.0802 (12) | |
H26 | 0.2085 | 0.3978 | 0.5526 | 0.096* | |
C27 | 0.2688 (4) | 0.36263 (16) | 0.4411 (3) | 0.0767 (11) | |
H27 | 0.3535 | 0.3684 | 0.4577 | 0.092* | |
C28 | 0.2336 (3) | 0.33635 (14) | 0.3596 (2) | 0.0650 (9) | |
H28 | 0.2937 | 0.3240 | 0.3217 | 0.078* | |
C29 | 0.5222 (5) | 0.4329 (2) | 0.9678 (4) | 0.1206 (19) | |
H29A | 0.5484 | 0.4009 | 0.9376 | 0.181* | |
H29B | 0.5781 | 0.4398 | 1.0215 | 0.181* | |
H29C | 0.5236 | 0.4628 | 0.9260 | 0.181* | |
C30 | 0.3907 (5) | 0.42520 (16) | 0.9965 (3) | 0.0848 (12) | |
C31 | 0.3687 (6) | 0.40379 (19) | 1.0822 (4) | 0.1083 (17) | |
H31 | 0.4355 | 0.3935 | 1.1233 | 0.130* | |
C32 | 0.2499 (7) | 0.39805 (19) | 1.1056 (3) | 0.1040 (17) | |
H32 | 0.2357 | 0.3842 | 1.1633 | 0.125* | |
C33 | 0.1481 (5) | 0.41253 (16) | 1.0448 (3) | 0.0836 (12) | |
C34 | 0.0234 (7) | 0.4081 (2) | 1.0641 (4) | 0.1109 (19) | |
H34 | 0.0054 | 0.3936 | 1.1207 | 0.133* | |
C35 | −0.0717 (6) | 0.4236 (2) | 1.0052 (5) | 0.1099 (19) | |
H35 | −0.1536 | 0.4205 | 1.0216 | 0.132* | |
C36 | −0.0483 (5) | 0.44495 (17) | 0.9178 (4) | 0.0929 (14) | |
C37 | −0.1403 (6) | 0.4617 (2) | 0.8523 (7) | 0.133 (3) | |
H37 | −0.2237 | 0.4594 | 0.8656 | 0.159* | |
C38 | −0.1130 (8) | 0.4816 (2) | 0.7681 (6) | 0.141 (3) | |
H38 | −0.1764 | 0.4926 | 0.7247 | 0.170* | |
C39 | 0.0158 (7) | 0.48497 (18) | 0.7488 (4) | 0.1102 (18) | |
C40 | 0.0548 (8) | 0.5065 (2) | 0.6580 (4) | 0.162 (3) | |
H40A | 0.0907 | 0.5416 | 0.6675 | 0.243* | |
H40B | −0.0173 | 0.5087 | 0.6144 | 0.243* | |
H40C | 0.1156 | 0.4828 | 0.6346 | 0.243* | |
C41 | 0.0765 (4) | 0.44945 (14) | 0.8927 (3) | 0.0722 (10) | |
C42 | 0.1765 (4) | 0.43374 (13) | 0.9578 (3) | 0.0670 (10) | |
O7 | −0.2628 (3) | 0.37352 (15) | 0.4519 (2) | 0.1150 (11) | |
H2W | −0.3165 | 0.3589 | 0.4818 | 0.172* | |
H1W | −0.2969 | 0.3827 | 0.3996 | 0.172* | |
O8 | −0.2740 (4) | 0.36941 (17) | 0.2523 (3) | 0.1431 (14) | |
H4W | −0.2110 | 0.3501 | 0.2421 | 0.215* | |
H3W | −0.2710 | 0.4016 | 0.2325 | 0.215* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.0433 (3) | 0.0551 (3) | 0.0423 (3) | 0.00193 (19) | 0.00362 (19) | 0.00095 (19) |
O1 | 0.0647 (15) | 0.0598 (13) | 0.0681 (14) | 0.0006 (11) | 0.0217 (12) | 0.0033 (11) |
O2 | 0.0637 (14) | 0.0533 (13) | 0.0692 (14) | 0.0057 (11) | 0.0214 (12) | 0.0033 (11) |
O3 | 0.198 (4) | 0.0631 (18) | 0.137 (3) | 0.015 (2) | 0.100 (3) | 0.0235 (18) |
O4 | 0.0550 (15) | 0.0795 (16) | 0.0576 (14) | −0.0023 (11) | −0.0028 (11) | −0.0154 (11) |
O5 | 0.0606 (14) | 0.0775 (16) | 0.0531 (13) | 0.0039 (12) | 0.0014 (11) | −0.0087 (12) |
O6 | 0.130 (3) | 0.102 (2) | 0.0547 (16) | −0.004 (2) | 0.0184 (17) | −0.0175 (15) |
N1 | 0.0409 (14) | 0.0437 (13) | 0.0441 (13) | 0.0009 (10) | 0.0001 (10) | −0.0021 (10) |
N2 | 0.0435 (14) | 0.0546 (14) | 0.0438 (13) | −0.0009 (11) | 0.0076 (11) | −0.0026 (11) |
N3 | 0.100 (3) | 0.0529 (18) | 0.083 (2) | 0.0053 (16) | −0.005 (2) | −0.0104 (16) |
N4 | 0.082 (2) | 0.0534 (17) | 0.076 (2) | 0.0055 (15) | 0.0108 (18) | −0.0059 (15) |
C1 | 0.0452 (19) | 0.075 (2) | 0.070 (2) | −0.0018 (16) | 0.0109 (16) | 0.0020 (18) |
C2 | 0.0419 (17) | 0.0480 (16) | 0.0577 (18) | −0.0005 (13) | −0.0007 (14) | −0.0080 (14) |
C3 | 0.0451 (19) | 0.068 (2) | 0.071 (2) | 0.0040 (15) | −0.0031 (17) | −0.0063 (17) |
C4 | 0.058 (2) | 0.067 (2) | 0.062 (2) | 0.0121 (16) | −0.0182 (17) | −0.0043 (17) |
C5 | 0.063 (2) | 0.0486 (17) | 0.0466 (17) | 0.0026 (14) | −0.0091 (15) | −0.0056 (13) |
C6 | 0.085 (3) | 0.063 (2) | 0.0452 (18) | 0.0078 (18) | −0.0082 (18) | 0.0017 (15) |
C7 | 0.101 (3) | 0.063 (2) | 0.0372 (17) | −0.004 (2) | 0.0049 (18) | 0.0013 (15) |
C8 | 0.072 (2) | 0.0553 (18) | 0.0418 (16) | −0.0081 (16) | 0.0127 (15) | −0.0069 (14) |
C9 | 0.075 (3) | 0.077 (2) | 0.0475 (19) | −0.0164 (19) | 0.0202 (18) | −0.0080 (17) |
C10 | 0.050 (2) | 0.091 (3) | 0.067 (2) | −0.0146 (18) | 0.0223 (18) | −0.012 (2) |
C11 | 0.0431 (18) | 0.067 (2) | 0.0555 (19) | −0.0043 (14) | 0.0078 (14) | −0.0079 (15) |
C12 | 0.0391 (18) | 0.099 (3) | 0.072 (2) | 0.0020 (17) | 0.0072 (16) | −0.006 (2) |
C13 | 0.0538 (18) | 0.0453 (16) | 0.0378 (15) | −0.0030 (13) | 0.0035 (13) | −0.0055 (12) |
C14 | 0.0492 (17) | 0.0402 (15) | 0.0428 (16) | −0.0003 (12) | 0.0010 (13) | −0.0071 (12) |
C15 | 0.0434 (17) | 0.0613 (19) | 0.0435 (16) | 0.0012 (14) | 0.0002 (13) | 0.0007 (14) |
C16 | 0.0556 (19) | 0.0512 (17) | 0.0491 (18) | 0.0031 (14) | 0.0019 (14) | −0.0009 (14) |
C17 | 0.077 (3) | 0.065 (2) | 0.081 (3) | 0.0072 (19) | 0.020 (2) | −0.0006 (19) |
C18 | 0.096 (3) | 0.065 (2) | 0.103 (3) | 0.018 (2) | 0.030 (3) | −0.008 (2) |
C19 | 0.117 (4) | 0.052 (2) | 0.087 (3) | 0.017 (2) | 0.022 (3) | 0.0040 (19) |
C20 | 0.119 (4) | 0.057 (2) | 0.078 (3) | 0.007 (2) | 0.035 (3) | 0.0093 (19) |
C21 | 0.089 (3) | 0.0513 (19) | 0.066 (2) | 0.0122 (18) | 0.023 (2) | 0.0055 (16) |
C22 | 0.061 (2) | 0.0515 (18) | 0.0473 (17) | −0.0044 (15) | 0.0028 (16) | 0.0039 (14) |
C23 | 0.061 (2) | 0.0486 (17) | 0.0444 (16) | −0.0067 (14) | −0.0036 (15) | 0.0059 (13) |
C24 | 0.074 (2) | 0.0529 (18) | 0.0491 (18) | −0.0082 (16) | −0.0004 (16) | 0.0030 (14) |
C25 | 0.104 (3) | 0.056 (2) | 0.0477 (19) | −0.0047 (19) | 0.002 (2) | 0.0032 (15) |
C26 | 0.114 (4) | 0.068 (2) | 0.054 (2) | −0.014 (2) | −0.024 (2) | 0.0009 (18) |
C27 | 0.079 (3) | 0.080 (3) | 0.066 (2) | −0.015 (2) | −0.023 (2) | 0.009 (2) |
C28 | 0.068 (2) | 0.064 (2) | 0.061 (2) | −0.0062 (17) | −0.0070 (17) | 0.0090 (17) |
C29 | 0.087 (4) | 0.099 (4) | 0.174 (6) | 0.014 (3) | 0.001 (4) | −0.024 (4) |
C30 | 0.102 (3) | 0.052 (2) | 0.098 (3) | 0.003 (2) | −0.003 (3) | −0.012 (2) |
C31 | 0.141 (5) | 0.075 (3) | 0.105 (4) | −0.003 (3) | −0.023 (4) | 0.003 (3) |
C32 | 0.164 (6) | 0.074 (3) | 0.073 (3) | −0.017 (3) | 0.006 (4) | 0.007 (2) |
C33 | 0.119 (4) | 0.055 (2) | 0.079 (3) | −0.015 (2) | 0.025 (3) | −0.008 (2) |
C34 | 0.148 (5) | 0.075 (3) | 0.118 (4) | −0.032 (3) | 0.065 (4) | −0.018 (3) |
C35 | 0.106 (4) | 0.075 (3) | 0.156 (6) | −0.025 (3) | 0.060 (4) | −0.031 (3) |
C36 | 0.079 (3) | 0.061 (2) | 0.139 (5) | −0.005 (2) | 0.013 (3) | −0.032 (3) |
C37 | 0.087 (4) | 0.083 (4) | 0.226 (8) | 0.006 (3) | −0.009 (5) | −0.053 (5) |
C38 | 0.137 (6) | 0.077 (4) | 0.196 (8) | 0.021 (4) | −0.072 (6) | −0.031 (4) |
C39 | 0.147 (5) | 0.058 (3) | 0.118 (4) | 0.011 (3) | −0.042 (4) | −0.016 (3) |
C40 | 0.289 (9) | 0.084 (4) | 0.101 (4) | 0.003 (5) | −0.064 (5) | 0.004 (3) |
C41 | 0.083 (3) | 0.0473 (19) | 0.088 (3) | −0.0022 (17) | 0.013 (2) | −0.0178 (19) |
C42 | 0.089 (3) | 0.0451 (18) | 0.068 (2) | −0.0070 (17) | 0.015 (2) | −0.0111 (16) |
O7 | 0.102 (2) | 0.146 (3) | 0.103 (2) | 0.002 (2) | 0.0468 (19) | 0.014 (2) |
O8 | 0.133 (3) | 0.114 (3) | 0.184 (4) | 0.020 (2) | 0.024 (3) | −0.014 (3) |
Mn1—O5 | 2.157 (2) | C16—C21 | 1.378 (5) |
Mn1—O1 | 2.210 (2) | C16—C17 | 1.380 (5) |
Mn1—N1 | 2.214 (2) | C17—C18 | 1.386 (6) |
Mn1—N2 | 2.261 (2) | C17—H17 | 0.9300 |
Mn1—O2 | 2.284 (2) | C18—C19 | 1.366 (6) |
Mn1—O4 | 2.329 (2) | C18—H18 | 0.9300 |
Mn1—C22 | 2.584 (3) | C19—C20 | 1.384 (5) |
Mn1—C15 | 2.612 (3) | C19—H19 | 0.9300 |
O1—C15 | 1.270 (4) | C20—C21 | 1.393 (5) |
O2—C15 | 1.251 (4) | C21—H21 | 0.9300 |
O3—C20 | 1.353 (5) | C22—C23 | 1.490 (4) |
O3—H3 | 0.8200 | C23—C24 | 1.372 (5) |
O4—C22 | 1.263 (4) | C23—C28 | 1.388 (5) |
O5—C22 | 1.266 (4) | C24—C25 | 1.395 (5) |
O6—C25 | 1.367 (5) | C24—H24 | 0.9300 |
O6—H6 | 0.8200 | C25—C26 | 1.378 (6) |
N1—C2 | 1.342 (4) | C26—C27 | 1.358 (6) |
N1—C14 | 1.360 (4) | C26—H26 | 0.9300 |
N2—C11 | 1.332 (4) | C27—C28 | 1.378 (5) |
N2—C13 | 1.367 (4) | C27—H27 | 0.9300 |
N3—C39 | 1.318 (6) | C28—H28 | 0.9300 |
N3—C41 | 1.360 (5) | C29—C30 | 1.511 (6) |
N4—C30 | 1.342 (5) | C29—H29A | 0.9600 |
N4—C42 | 1.354 (5) | C29—H29B | 0.9600 |
C1—C2 | 1.483 (5) | C29—H29C | 0.9600 |
C1—H1A | 0.9600 | C30—C31 | 1.390 (7) |
C1—H1B | 0.9600 | C31—C32 | 1.348 (7) |
C1—H1C | 0.9600 | C31—H31 | 0.9300 |
C2—C3 | 1.398 (4) | C32—C33 | 1.395 (7) |
C3—C4 | 1.348 (5) | C32—H32 | 0.9300 |
C3—H3A | 0.9300 | C33—C34 | 1.389 (7) |
C4—C5 | 1.415 (5) | C33—C42 | 1.423 (6) |
C4—H4 | 0.9300 | C34—C35 | 1.334 (8) |
C5—C14 | 1.402 (4) | C34—H34 | 0.9300 |
C5—C6 | 1.422 (5) | C35—C36 | 1.414 (8) |
C6—C7 | 1.324 (5) | C35—H35 | 0.9300 |
C6—H6A | 0.9300 | C36—C37 | 1.378 (9) |
C7—C8 | 1.441 (5) | C36—C41 | 1.416 (6) |
C7—H7 | 0.9300 | C37—C38 | 1.371 (9) |
C8—C13 | 1.401 (4) | C37—H37 | 0.9300 |
C8—C9 | 1.408 (5) | C38—C39 | 1.430 (9) |
C9—C10 | 1.348 (5) | C38—H38 | 0.9300 |
C9—H9 | 0.9300 | C39—C40 | 1.511 (8) |
C10—C11 | 1.417 (5) | C40—H40A | 0.9600 |
C10—H10 | 0.9300 | C40—H40B | 0.9600 |
C11—C12 | 1.496 (5) | C40—H40C | 0.9600 |
C12—H12A | 0.9600 | C41—C42 | 1.424 (6) |
C12—H12B | 0.9600 | O7—H2W | 0.8299 |
C12—H12C | 0.9600 | O7—H1W | 0.8468 |
C13—C14 | 1.443 (4) | O8—H4W | 0.8502 |
C15—C16 | 1.495 (4) | O8—H3W | 0.8517 |
O5—Mn1—O1 | 104.63 (9) | O1—C15—Mn1 | 57.64 (16) |
O5—Mn1—N1 | 139.36 (9) | C16—C15—Mn1 | 177.6 (2) |
O1—Mn1—N1 | 114.97 (9) | C21—C16—C17 | 119.8 (3) |
O5—Mn1—N2 | 96.42 (9) | C21—C16—C15 | 120.2 (3) |
O1—Mn1—N2 | 90.59 (9) | C17—C16—C15 | 120.0 (3) |
N1—Mn1—N2 | 75.15 (9) | C16—C17—C18 | 119.8 (4) |
O5—Mn1—O2 | 99.97 (9) | C16—C17—H17 | 120.1 |
O1—Mn1—O2 | 57.67 (8) | C18—C17—H17 | 120.1 |
N1—Mn1—O2 | 108.35 (9) | C19—C18—C17 | 120.5 (4) |
N2—Mn1—O2 | 147.03 (9) | C19—C18—H18 | 119.7 |
O5—Mn1—O4 | 58.41 (8) | C17—C18—H18 | 119.7 |
O1—Mn1—O4 | 142.02 (9) | C18—C19—C20 | 120.2 (4) |
N1—Mn1—O4 | 92.49 (8) | C18—C19—H19 | 119.9 |
N2—Mn1—O4 | 122.94 (9) | C20—C19—H19 | 119.9 |
O2—Mn1—O4 | 89.96 (8) | O3—C20—C19 | 117.3 (4) |
O5—Mn1—C22 | 29.24 (9) | O3—C20—C21 | 123.4 (4) |
O1—Mn1—C22 | 125.81 (10) | C19—C20—C21 | 119.3 (4) |
N1—Mn1—C22 | 117.96 (10) | C16—C21—C20 | 120.3 (3) |
N2—Mn1—C22 | 113.02 (9) | C16—C21—H21 | 119.8 |
O2—Mn1—C22 | 94.59 (9) | C20—C21—H21 | 119.8 |
O4—Mn1—C22 | 29.20 (9) | O4—C22—O5 | 120.3 (3) |
O5—Mn1—C15 | 103.86 (9) | O4—C22—C23 | 120.6 (3) |
O1—Mn1—C15 | 29.05 (8) | O5—C22—C23 | 119.1 (3) |
N1—Mn1—C15 | 115.03 (9) | O4—C22—Mn1 | 64.12 (17) |
N2—Mn1—C15 | 119.24 (9) | O5—C22—Mn1 | 56.31 (16) |
O2—Mn1—C15 | 28.62 (8) | C23—C22—Mn1 | 174.8 (2) |
O4—Mn1—C15 | 116.44 (9) | C24—C23—C28 | 120.1 (3) |
C22—Mn1—C15 | 112.04 (9) | C24—C23—C22 | 119.3 (3) |
C15—O1—Mn1 | 93.31 (18) | C28—C23—C22 | 120.6 (3) |
C15—O2—Mn1 | 90.38 (18) | C23—C24—C25 | 120.4 (3) |
C20—O3—H3 | 109.5 | C23—C24—H24 | 119.8 |
C22—O4—Mn1 | 86.67 (19) | C25—C24—H24 | 119.8 |
C22—O5—Mn1 | 94.5 (2) | O6—C25—C26 | 119.6 (4) |
C25—O6—H6 | 109.5 | O6—C25—C24 | 121.5 (4) |
C2—N1—C14 | 119.2 (2) | C26—C25—C24 | 118.9 (4) |
C2—N1—Mn1 | 125.6 (2) | C27—C26—C25 | 120.4 (4) |
C14—N1—Mn1 | 115.12 (18) | C27—C26—H26 | 119.8 |
C11—N2—C13 | 119.0 (3) | C25—C26—H26 | 119.8 |
C11—N2—Mn1 | 127.5 (2) | C26—C27—C28 | 121.4 (4) |
C13—N2—Mn1 | 113.44 (18) | C26—C27—H27 | 119.3 |
C39—N3—C41 | 119.4 (5) | C28—C27—H27 | 119.3 |
C30—N4—C42 | 119.2 (4) | C27—C28—C23 | 118.8 (4) |
C2—C1—H1A | 109.5 | C27—C28—H28 | 120.6 |
C2—C1—H1B | 109.5 | C23—C28—H28 | 120.6 |
H1A—C1—H1B | 109.5 | C30—C29—H29A | 109.5 |
C2—C1—H1C | 109.5 | C30—C29—H29B | 109.5 |
H1A—C1—H1C | 109.5 | H29A—C29—H29B | 109.5 |
H1B—C1—H1C | 109.5 | C30—C29—H29C | 109.5 |
N1—C2—C3 | 120.4 (3) | H29A—C29—H29C | 109.5 |
N1—C2—C1 | 119.0 (3) | H29B—C29—H29C | 109.5 |
C3—C2—C1 | 120.5 (3) | N4—C30—C31 | 121.6 (5) |
C4—C3—C2 | 121.0 (3) | N4—C30—C29 | 116.9 (5) |
C4—C3—H3A | 119.5 | C31—C30—C29 | 121.5 (5) |
C2—C3—H3A | 119.5 | C32—C31—C30 | 119.7 (5) |
C3—C4—C5 | 119.9 (3) | C32—C31—H31 | 120.2 |
C3—C4—H4 | 120.0 | C30—C31—H31 | 120.2 |
C5—C4—H4 | 120.0 | C31—C32—C33 | 121.3 (5) |
C14—C5—C4 | 116.5 (3) | C31—C32—H32 | 119.4 |
C14—C5—C6 | 120.1 (3) | C33—C32—H32 | 119.4 |
C4—C5—C6 | 123.4 (3) | C34—C33—C32 | 124.5 (5) |
C7—C6—C5 | 121.2 (3) | C34—C33—C42 | 119.0 (5) |
C7—C6—H6A | 119.4 | C32—C33—C42 | 116.5 (4) |
C5—C6—H6A | 119.4 | C35—C34—C33 | 122.9 (6) |
C6—C7—C8 | 121.1 (3) | C35—C34—H34 | 118.5 |
C6—C7—H7 | 119.4 | C33—C34—H34 | 118.5 |
C8—C7—H7 | 119.4 | C34—C35—C36 | 120.2 (5) |
C13—C8—C9 | 117.2 (3) | C34—C35—H35 | 119.9 |
C13—C8—C7 | 119.3 (3) | C36—C35—H35 | 119.9 |
C9—C8—C7 | 123.5 (3) | C37—C36—C35 | 124.3 (6) |
C10—C9—C8 | 119.8 (3) | C37—C36—C41 | 115.9 (6) |
C10—C9—H9 | 120.1 | C35—C36—C41 | 119.8 (5) |
C8—C9—H9 | 120.1 | C38—C37—C36 | 122.2 (7) |
C9—C10—C11 | 120.7 (3) | C38—C37—H37 | 118.9 |
C9—C10—H10 | 119.7 | C36—C37—H37 | 118.9 |
C11—C10—H10 | 119.7 | C37—C38—C39 | 118.2 (6) |
N2—C11—C10 | 120.7 (3) | C37—C38—H38 | 120.9 |
N2—C11—C12 | 118.3 (3) | C39—C38—H38 | 120.9 |
C10—C11—C12 | 121.0 (3) | N3—C39—C38 | 121.2 (6) |
C11—C12—H12A | 109.5 | N3—C39—C40 | 116.9 (6) |
C11—C12—H12B | 109.5 | C38—C39—C40 | 121.8 (6) |
H12A—C12—H12B | 109.5 | C39—C40—H40A | 109.5 |
C11—C12—H12C | 109.5 | C39—C40—H40B | 109.5 |
H12A—C12—H12C | 109.5 | H40A—C40—H40B | 109.5 |
H12B—C12—H12C | 109.5 | C39—C40—H40C | 109.5 |
N2—C13—C8 | 122.7 (3) | H40A—C40—H40C | 109.5 |
N2—C13—C14 | 118.0 (2) | H40B—C40—H40C | 109.5 |
C8—C13—C14 | 119.3 (3) | N3—C41—C36 | 123.1 (5) |
N1—C14—C5 | 122.8 (3) | N3—C41—C42 | 118.0 (4) |
N1—C14—C13 | 118.3 (3) | C36—C41—C42 | 118.9 (4) |
C5—C14—C13 | 118.9 (3) | N4—C42—C33 | 121.8 (4) |
O2—C15—O1 | 118.6 (3) | N4—C42—C41 | 119.0 (4) |
O2—C15—C16 | 121.2 (3) | C33—C42—C41 | 119.2 (4) |
O1—C15—C16 | 120.1 (3) | H2W—O7—H1W | 108.5 |
O2—C15—Mn1 | 61.00 (16) | H4W—O8—H3W | 114.8 |
O5—Mn1—O1—C15 | 92.30 (19) | Mn1—O2—C15—O1 | −0.6 (3) |
N1—Mn1—O1—C15 | −97.05 (19) | Mn1—O2—C15—C16 | 179.0 (3) |
N2—Mn1—O1—C15 | −170.92 (19) | Mn1—O1—C15—O2 | 0.7 (3) |
O2—Mn1—O1—C15 | −0.37 (17) | Mn1—O1—C15—C16 | −179.0 (2) |
O4—Mn1—O1—C15 | 35.4 (3) | O5—Mn1—C15—O2 | 85.42 (19) |
C22—Mn1—O1—C15 | 69.8 (2) | O1—Mn1—C15—O2 | −179.3 (3) |
O5—Mn1—O2—C15 | −100.70 (19) | N1—Mn1—C15—O2 | −82.51 (19) |
O1—Mn1—O2—C15 | 0.38 (17) | N2—Mn1—C15—O2 | −168.92 (17) |
N1—Mn1—O2—C15 | 108.83 (18) | O4—Mn1—C15—O2 | 24.1 (2) |
N2—Mn1—O2—C15 | 18.0 (3) | C22—Mn1—C15—O2 | 55.8 (2) |
O4—Mn1—O2—C15 | −158.56 (19) | O5—Mn1—C15—O1 | −95.24 (19) |
C22—Mn1—O2—C15 | −129.69 (19) | N1—Mn1—C15—O1 | 96.83 (19) |
O5—Mn1—O4—C22 | −2.24 (17) | N2—Mn1—C15—O1 | 10.4 (2) |
O1—Mn1—O4—C22 | 69.9 (2) | O2—Mn1—C15—O1 | 179.3 (3) |
N1—Mn1—O4—C22 | −152.12 (18) | O4—Mn1—C15—O1 | −156.56 (17) |
N2—Mn1—O4—C22 | −78.2 (2) | C22—Mn1—C15—O1 | −124.82 (19) |
O2—Mn1—O4—C22 | 99.51 (19) | O2—C15—C16—C21 | 2.4 (5) |
C15—Mn1—O4—C22 | 88.24 (19) | O1—C15—C16—C21 | −177.9 (3) |
O1—Mn1—O5—C22 | −140.49 (18) | O2—C15—C16—C17 | −176.9 (3) |
N1—Mn1—O5—C22 | 52.6 (2) | O1—C15—C16—C17 | 2.8 (5) |
N2—Mn1—O5—C22 | 127.21 (19) | C21—C16—C17—C18 | 0.6 (6) |
O2—Mn1—O5—C22 | −81.51 (19) | C15—C16—C17—C18 | 179.9 (4) |
O4—Mn1—O5—C22 | 2.24 (17) | C16—C17—C18—C19 | 0.0 (7) |
C15—Mn1—O5—C22 | −110.51 (19) | C17—C18—C19—C20 | −0.3 (7) |
O5—Mn1—N1—C2 | −95.7 (2) | C18—C19—C20—O3 | 178.9 (5) |
O1—Mn1—N1—C2 | 98.3 (2) | C18—C19—C20—C21 | 0.0 (7) |
N2—Mn1—N1—C2 | −178.1 (2) | C17—C16—C21—C20 | −0.9 (6) |
O2—Mn1—N1—C2 | 36.1 (2) | C15—C16—C21—C20 | 179.8 (4) |
O4—Mn1—N1—C2 | −54.7 (2) | O3—C20—C21—C16 | −178.2 (4) |
C22—Mn1—N1—C2 | −69.6 (2) | C19—C20—C21—C16 | 0.6 (7) |
C15—Mn1—N1—C2 | 66.1 (2) | Mn1—O4—C22—O5 | 3.8 (3) |
O5—Mn1—N1—C14 | 83.3 (2) | Mn1—O4—C22—C23 | −177.4 (3) |
O1—Mn1—N1—C14 | −82.7 (2) | Mn1—O5—C22—O4 | −4.1 (3) |
N2—Mn1—N1—C14 | 0.88 (18) | Mn1—O5—C22—C23 | 177.1 (2) |
O2—Mn1—N1—C14 | −144.85 (18) | O5—Mn1—C22—O4 | 176.1 (3) |
O4—Mn1—N1—C14 | 124.36 (19) | O1—Mn1—C22—O4 | −134.53 (17) |
C22—Mn1—N1—C14 | 109.39 (19) | N1—Mn1—C22—O4 | 31.9 (2) |
C15—Mn1—N1—C14 | −114.83 (19) | N2—Mn1—C22—O4 | 116.79 (18) |
O5—Mn1—N2—C11 | 40.9 (3) | O2—Mn1—C22—O4 | −81.66 (18) |
O1—Mn1—N2—C11 | −63.9 (3) | C15—Mn1—C22—O4 | −105.09 (19) |
N1—Mn1—N2—C11 | −179.7 (3) | O1—Mn1—C22—O5 | 49.4 (2) |
O2—Mn1—N2—C11 | −78.7 (3) | N1—Mn1—C22—O5 | −144.16 (18) |
O4—Mn1—N2—C11 | 97.1 (3) | N2—Mn1—C22—O5 | −59.3 (2) |
C22—Mn1—N2—C11 | 65.9 (3) | O2—Mn1—C22—O5 | 102.25 (19) |
C15—Mn1—N2—C11 | −69.0 (3) | O4—Mn1—C22—O5 | −176.1 (3) |
O5—Mn1—N2—C13 | −139.89 (19) | C15—Mn1—C22—O5 | 78.8 (2) |
O1—Mn1—N2—C13 | 115.3 (2) | O4—C22—C23—C24 | 15.0 (4) |
N1—Mn1—N2—C13 | −0.41 (18) | O5—C22—C23—C24 | −166.2 (3) |
O2—Mn1—N2—C13 | 100.5 (2) | O4—C22—C23—C28 | −166.6 (3) |
O4—Mn1—N2—C13 | −83.6 (2) | O5—C22—C23—C28 | 12.2 (4) |
C22—Mn1—N2—C13 | −114.9 (2) | C28—C23—C24—C25 | 0.6 (5) |
C15—Mn1—N2—C13 | 110.3 (2) | C22—C23—C24—C25 | 179.1 (3) |
C14—N1—C2—C3 | 0.1 (4) | C23—C24—C25—O6 | −179.7 (3) |
Mn1—N1—C2—C3 | 179.1 (2) | C23—C24—C25—C26 | 0.0 (5) |
C14—N1—C2—C1 | 179.1 (3) | O6—C25—C26—C27 | 179.6 (4) |
Mn1—N1—C2—C1 | −1.9 (4) | C24—C25—C26—C27 | −0.2 (6) |
N1—C2—C3—C4 | 1.2 (5) | C25—C26—C27—C28 | −0.3 (6) |
C1—C2—C3—C4 | −177.8 (3) | C26—C27—C28—C23 | 0.8 (6) |
C2—C3—C4—C5 | −1.3 (5) | C24—C23—C28—C27 | −1.0 (5) |
C3—C4—C5—C14 | 0.1 (5) | C22—C23—C28—C27 | −179.5 (3) |
C3—C4—C5—C6 | −178.8 (3) | C42—N4—C30—C31 | −0.1 (6) |
C14—C5—C6—C7 | −1.5 (5) | C42—N4—C30—C29 | 179.8 (3) |
C4—C5—C6—C7 | 177.5 (3) | N4—C30—C31—C32 | −0.7 (7) |
C5—C6—C7—C8 | 0.8 (5) | C29—C30—C31—C32 | 179.4 (4) |
C6—C7—C8—C13 | 0.2 (5) | C30—C31—C32—C33 | 0.9 (7) |
C6—C7—C8—C9 | −179.8 (3) | C31—C32—C33—C34 | −179.6 (5) |
C13—C8—C9—C10 | 2.2 (5) | C31—C32—C33—C42 | −0.3 (7) |
C7—C8—C9—C10 | −177.7 (3) | C32—C33—C34—C35 | 178.2 (5) |
C8—C9—C10—C11 | −2.5 (5) | C42—C33—C34—C35 | −1.1 (7) |
C13—N2—C11—C10 | 0.5 (5) | C33—C34—C35—C36 | 1.2 (8) |
Mn1—N2—C11—C10 | 179.7 (2) | C34—C35—C36—C37 | 179.5 (5) |
C13—N2—C11—C12 | 179.8 (3) | C34—C35—C36—C41 | 0.3 (7) |
Mn1—N2—C11—C12 | −0.9 (4) | C35—C36—C37—C38 | −179.4 (5) |
C9—C10—C11—N2 | 1.1 (5) | C41—C36—C37—C38 | −0.2 (8) |
C9—C10—C11—C12 | −178.2 (3) | C36—C37—C38—C39 | −0.1 (9) |
C11—N2—C13—C8 | −0.7 (4) | C41—N3—C39—C38 | 0.4 (6) |
Mn1—N2—C13—C8 | 180.0 (2) | C41—N3—C39—C40 | −179.7 (4) |
C11—N2—C13—C14 | 179.2 (3) | C37—C38—C39—N3 | 0.0 (8) |
Mn1—N2—C13—C14 | −0.1 (3) | C37—C38—C39—C40 | −179.9 (5) |
C9—C8—C13—N2 | −0.6 (4) | C39—N3—C41—C36 | −0.7 (5) |
C7—C8—C13—N2 | 179.3 (3) | C39—N3—C41—C42 | −179.1 (3) |
C9—C8—C13—C14 | 179.5 (3) | C37—C36—C41—N3 | 0.6 (6) |
C7—C8—C13—C14 | −0.6 (4) | C35—C36—C41—N3 | 179.8 (4) |
C2—N1—C14—C5 | −1.3 (4) | C37—C36—C41—C42 | 178.9 (4) |
Mn1—N1—C14—C5 | 179.6 (2) | C35—C36—C41—C42 | −1.8 (5) |
C2—N1—C14—C13 | 177.8 (2) | C30—N4—C42—C33 | 0.7 (5) |
Mn1—N1—C14—C13 | −1.3 (3) | C30—N4—C42—C41 | 180.0 (3) |
C4—C5—C14—N1 | 1.1 (4) | C34—C33—C42—N4 | 178.9 (4) |
C6—C5—C14—N1 | −179.8 (3) | C32—C33—C42—N4 | −0.5 (5) |
C4—C5—C14—C13 | −178.0 (3) | C34—C33—C42—C41 | −0.4 (5) |
C6—C5—C14—C13 | 1.1 (4) | C32—C33—C42—C41 | −179.8 (3) |
N2—C13—C14—N1 | 0.9 (4) | N3—C41—C42—N4 | 0.9 (5) |
C8—C13—C14—N1 | −179.2 (3) | C36—C41—C42—N4 | −177.5 (3) |
N2—C13—C14—C5 | −179.9 (3) | N3—C41—C42—C33 | −179.7 (3) |
C8—C13—C14—C5 | 0.0 (4) | C36—C41—C42—C33 | 1.8 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6···O7 | 0.82 | 1.89 | 2.709 (5) | 179 |
O7—H1W···O8 | 0.85 | 2.20 | 2.891 (6) | 139 |
O8—H4W···O4 | 0.85 | 2.17 | 3.020 (4) | 179 |
O7—H2W···O1i | 0.83 | 1.96 | 2.774 (4) | 165 |
O8—H3W···O3ii | 0.85 | 2.16 | 2.943 (5) | 153 |
O3—H3···N4iii | 0.82 | 2.15 | 2.964 (5) | 175 |
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) −x−1/2, y+1/2, −z+1/2; (iii) x−1/2, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Mn(C7H5O3)2(C14H12N2)]·C14H12N2·2H2O |
Mr | 781.70 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 291 |
a, b, c (Å) | 10.7010 (9), 24.865 (2), 14.5083 (12) |
β (°) | 94.514 (1) |
V (Å3) | 3848.5 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.40 |
Crystal size (mm) | 0.34 × 0.25 × 0.24 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS in SAINT; Bruker, 1997) |
Tmin, Tmax | 0.876, 0.910 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26490, 7162, 5040 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.170, 1.03 |
No. of reflections | 7162 |
No. of parameters | 502 |
No. of restraints | 18 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.87, −0.37 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1990).
Mn1—O5 | 2.157 (2) | Mn1—N2 | 2.261 (2) |
Mn1—O1 | 2.210 (2) | Mn1—O2 | 2.284 (2) |
Mn1—N1 | 2.214 (2) | Mn1—O4 | 2.329 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6···O7 | 0.82 | 1.89 | 2.709 (5) | 178.9 |
O7—H1W···O8 | 0.85 | 2.20 | 2.891 (6) | 139.3 |
O8—H4W···O4 | 0.85 | 2.17 | 3.020 (4) | 179.4 |
O7—H2W···O1i | 0.83 | 1.96 | 2.774 (4) | 165.3 |
O8—H3W···O3ii | 0.85 | 2.16 | 2.943 (5) | 152.9 |
O3—H3···N4iii | 0.82 | 2.15 | 2.964 (5) | 175.1 |
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) −x−1/2, y+1/2, −z+1/2; (iii) x−1/2, −y+1/2, z−1/2. |
Crystal structures of metal complexes of 1,10-phenanthroline or its derivatives combinated with benzoic anions have been reported (Fu et al., 2006; Liu & Ng, 2007; Niu et al., 2002; Pan, Liu et al., 2006; Pan, Su et al., 2006a,b; Shi et al., 2001; Su, Gu et al., 2005a,b; Su & Xu, 2005; Su, Zhang & Xu,2005; Xu et al., 2004). Recently, as part of our ongoing studies (Xuan, Zhao & Tang, 2007; Xuan, Zhao & Zhang, 2007); Zhao, Xuan & Wang, 2007; Zhao, Yan et al., 2007) of mixed-ligand complexes, we have reported the structure of bis(benzoato-κ2O,O')(2,9-dimethyl-1,10-phenanthroline-κ2N,N') manganese(II) (Zhao, Xuan et al., 2007). In this paper, we present the crystal structure of the manganese complex of dmphen and 3-hydroxy-benzoate anion, [Mn(C7H5O3)2(C14H12N2)]. (C14H12N2).2H2O, (I) which was obtained by reaction of dmphen, sodium 3-hydroxy-benzoate and Mn(NO3)2 aqueous solutions.
As shown in Fig. 1, the structure unit of (I) is composed of a MnII complex, [Mn(C7H5O3)2(C14H12N2)], one non-coordinated dmphen molecule and two crystal water molecules. Two N atoms of one dmphen ligand and four O atoms of two 3-hydroxy-benzoate anions are coordinated to the MnII ion in a strongly distorted octahedral arrangement. The corresponding bond lengths are listed in Table 1.
The crystal structure of (I) is stabilized by a profuse network of O—H···O and O—H···N hydrogen bonds having water molecules and the 3-hydroxy-benzoate anion as donors and the same groups plus the non-coordinated dmphen molecule as acceptors (Table 2 and Fig. 2).