Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807061077/bh2148sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807061077/bh2148Isup2.hkl |
CCDC reference: 672767
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.004 Å
- R factor = 0.042
- wR factor = 0.128
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C35 - C43 .. 5.56 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C42 - C43 .. 6.89 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mn1 - O1 .. 8.20 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mn1 - O7 .. 7.36 su PLAT417_ALERT_2_C Short Inter D-H..H-D H3W .. H8 .. 2.11 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H4W .. N3 .. 2.67 Ang.
Alert level G RADNT01_ALERT_1_G Extra text has been found in the _diffrn_radiation_type field. Radiation given as MoK\a radiation Radiation identified as Mo K\a 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 6 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 5 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
For structures of related MnII complexes, see: Pan et al. (2006); Su et al. (2005); Wang et al. (2003, 2004); Xiao (2005); Xuan et al. (2007); Yang et al. (2006); Zhang (2006); Zhao et al. (2007).
The reaction of 4-hydroxybenzoate (0.069 g, 0.5 mmol) and NaOH (0.018 g, 0.5 mmol) in ethanol/water (v:v=1:1, 10 ml) at room temperature for 1 h. produced a colorless solutions, to which 2,9-dimethyl-1,10-phenanthroline (C14H12N2.0.5H2O, 0.109 g, 0.5 mmol) and a 50% Mn(NO3)2 aqueous solution (0.146 g, 0.5 mmol) in ethanol/water (v:v=2:1, 10 ml) mixture was added. The resulting solution was stirred for 5 h. at 323 K and then a yellow precipitate was filtered. Yellow single crystals of (I) were obtained by slow evaporation of the filtrate over 2 days.
C-bonded H atoms were placed in calculated positions, with C—H = 0.93 (aromatic CH), 0.97 (methylene CH2) or C—H = 0.96 Å (methyl CH3), and refined in the riding-model approximation with Uiso(H) = 1.5Ueq(C) for methyl groups and Uiso(H) = 1.2Ueq(C) otherwise. Hydroxyl and water H atoms were found in a difference map and their coordinates fixed. Isotropic displacement parameters were fixed to Uiso(H) = 1.5Ueq(O).
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 (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).
[Mn(C7H5O3)2(C14H12N2)(H2O)]·C14H12N2·C2H6O·H2O | F(000) = 1732 |
Mr = 827.77 | Dx = 1.345 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8290 reflections |
a = 15.9080 (12) Å | θ = 2.6–24.1° |
b = 18.4137 (14) Å | µ = 0.38 mm−1 |
c = 15.4744 (11) Å | T = 297 K |
β = 115.585 (1)° | Block, yellow |
V = 4088.4 (5) Å3 | 0.48 × 0.35 × 0.29 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 7614 independent reflections |
Radiation source: fine-focus sealed tube | 5682 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ϕ and ω scans | θmax = 25.5°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −19→19 |
Tmin = 0.838, Tmax = 0.896 | k = −22→22 |
30925 measured reflections | l = −18→18 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0656P)2 + 1.2395P] where P = (Fo2 + 2Fc2)/3 |
7614 reflections | (Δ/σ)max = 0.001 |
532 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
[Mn(C7H5O3)2(C14H12N2)(H2O)]·C14H12N2·C2H6O·H2O | V = 4088.4 (5) Å3 |
Mr = 827.77 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.9080 (12) Å | µ = 0.38 mm−1 |
b = 18.4137 (14) Å | T = 297 K |
c = 15.4744 (11) Å | 0.48 × 0.35 × 0.29 mm |
β = 115.585 (1)° |
Bruker SMART CCD area-detector diffractometer | 7614 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 5682 reflections with I > 2σ(I) |
Tmin = 0.838, Tmax = 0.896 | Rint = 0.027 |
30925 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.29 e Å−3 |
7614 reflections | Δρmin = −0.34 e Å−3 |
532 parameters |
x | y | z | Uiso*/Ueq | ||
Mn1 | 0.39251 (2) | 0.324065 (17) | 0.10749 (2) | 0.04676 (12) | |
O1 | 0.49765 (11) | 0.29788 (10) | 0.05292 (11) | 0.0607 (4) | |
O2 | 0.55171 (11) | 0.31851 (9) | 0.20570 (12) | 0.0612 (4) | |
O3 | 0.91738 (15) | 0.20101 (14) | 0.17976 (18) | 0.0953 (7) | |
H3 | 0.9556 | 0.2035 | 0.2360 | 0.143* | |
O4 | 0.36118 (12) | 0.21099 (9) | 0.10766 (12) | 0.0621 (4) | |
O5 | 0.22988 (13) | 0.18962 (9) | −0.02313 (13) | 0.0723 (5) | |
O6 | 0.34146 (14) | −0.13266 (9) | 0.12067 (12) | 0.0716 (5) | |
H6 | 0.3770 | −0.1421 | 0.1764 | 0.107* | |
O7 | 0.26701 (12) | 0.32769 (9) | −0.02475 (13) | 0.0676 (5) | |
H1W | 0.2456 | 0.2866 | −0.0390 | 0.101* | |
H2W | 0.2261 | 0.3565 | −0.0255 | 0.101* | |
O8 | −0.0490 (2) | 0.84383 (19) | 0.0833 (2) | 0.1286 (10) | |
H8 | −0.1056 | 0.8406 | 0.0646 | 0.193* | |
O9 | 0.03962 (15) | 0.20203 (14) | 0.3624 (2) | 0.1172 (9) | |
H3W | 0.0509 | 0.2343 | 0.4049 | 0.176* | |
H4W | 0.0622 | 0.1629 | 0.3911 | 0.176* | |
N1 | 0.39368 (12) | 0.36568 (10) | 0.24646 (13) | 0.0482 (4) | |
N2 | 0.38111 (12) | 0.44827 (10) | 0.09324 (13) | 0.0494 (4) | |
N3 | 0.13868 (14) | 0.38424 (12) | 0.07226 (16) | 0.0631 (5) | |
N4 | 0.12798 (16) | 0.44918 (12) | −0.09163 (16) | 0.0694 (6) | |
C1 | 0.41119 (17) | 0.32609 (14) | 0.32510 (17) | 0.0567 (6) | |
C2 | 0.42060 (19) | 0.35868 (17) | 0.41084 (19) | 0.0684 (7) | |
H2 | 0.4336 | 0.3301 | 0.4647 | 0.082* | |
C3 | 0.41081 (19) | 0.43131 (17) | 0.4155 (2) | 0.0704 (7) | |
H3A | 0.4164 | 0.4526 | 0.4723 | 0.084* | |
C4 | 0.39219 (17) | 0.47455 (14) | 0.33455 (19) | 0.0613 (6) | |
C5 | 0.3805 (2) | 0.55136 (17) | 0.3346 (2) | 0.0786 (8) | |
H5 | 0.3828 | 0.5741 | 0.3892 | 0.094* | |
C6 | 0.3665 (2) | 0.59097 (16) | 0.2571 (3) | 0.0810 (9) | |
H6A | 0.3577 | 0.6408 | 0.2583 | 0.097* | |
C7 | 0.36476 (17) | 0.55819 (13) | 0.1724 (2) | 0.0650 (7) | |
C8 | 0.3549 (2) | 0.59773 (15) | 0.0915 (3) | 0.0785 (9) | |
H8A | 0.3456 | 0.6477 | 0.0897 | 0.094* | |
C9 | 0.3588 (2) | 0.56367 (16) | 0.0159 (2) | 0.0773 (8) | |
H9 | 0.3517 | 0.5903 | −0.0379 | 0.093* | |
C10 | 0.37371 (16) | 0.48792 (14) | 0.01812 (18) | 0.0597 (6) | |
C11 | 0.37580 (15) | 0.48233 (12) | 0.16950 (17) | 0.0508 (5) | |
C12 | 0.38662 (15) | 0.43933 (12) | 0.25134 (16) | 0.0494 (5) | |
C13 | 0.4220 (2) | 0.24625 (15) | 0.3212 (2) | 0.0781 (8) | |
H13A | 0.3638 | 0.2253 | 0.2776 | 0.117* | |
H13B | 0.4402 | 0.2260 | 0.3839 | 0.117* | |
H13C | 0.4689 | 0.2358 | 0.2996 | 0.117* | |
C14 | 0.3833 (2) | 0.45073 (17) | −0.0631 (2) | 0.0761 (8) | |
H14A | 0.4359 | 0.4185 | −0.0382 | 0.114* | |
H14B | 0.3924 | 0.4864 | −0.1035 | 0.114* | |
H14C | 0.3278 | 0.4234 | −0.0996 | 0.114* | |
C15 | 0.56467 (15) | 0.29844 (11) | 0.13417 (16) | 0.0468 (5) | |
C16 | 0.65894 (15) | 0.27431 (11) | 0.14719 (16) | 0.0449 (5) | |
C17 | 0.67156 (17) | 0.24486 (12) | 0.07141 (17) | 0.0533 (6) | |
H17 | 0.6208 | 0.2408 | 0.0118 | 0.064* | |
C18 | 0.75787 (19) | 0.22137 (13) | 0.0825 (2) | 0.0624 (6) | |
H18 | 0.7654 | 0.2026 | 0.0305 | 0.075* | |
C19 | 0.83286 (18) | 0.22581 (13) | 0.1710 (2) | 0.0637 (7) | |
C20 | 0.82175 (17) | 0.25559 (14) | 0.2474 (2) | 0.0649 (7) | |
H20 | 0.8726 | 0.2595 | 0.3069 | 0.078* | |
C21 | 0.73571 (16) | 0.27942 (13) | 0.23550 (18) | 0.0570 (6) | |
H21 | 0.7287 | 0.2993 | 0.2873 | 0.068* | |
C22 | 0.29848 (18) | 0.16912 (12) | 0.05170 (18) | 0.0542 (6) | |
C23 | 0.30779 (16) | 0.08987 (12) | 0.07469 (16) | 0.0501 (5) | |
C24 | 0.25473 (19) | 0.03984 (14) | 0.00593 (17) | 0.0658 (7) | |
H24 | 0.2099 | 0.0565 | −0.0526 | 0.079* | |
C25 | 0.2665 (2) | −0.03391 (14) | 0.02191 (17) | 0.0678 (7) | |
H25 | 0.2308 | −0.0663 | −0.0260 | 0.081* | |
C26 | 0.33145 (17) | −0.05972 (13) | 0.10953 (16) | 0.0535 (6) | |
C28 | 0.37170 (16) | 0.06317 (13) | 0.16186 (17) | 0.0556 (6) | |
H28 | 0.4082 | 0.0955 | 0.2094 | 0.067* | |
C29 | −0.0294 (4) | 0.8918 (3) | 0.0229 (4) | 0.1507 (19) | |
H29A | −0.0326 | 0.9415 | 0.0422 | 0.181* | |
H29B | −0.0763 | 0.8859 | −0.0425 | 0.181* | |
C30 | 0.0611 (4) | 0.8789 (4) | 0.0266 (4) | 0.191 (3) | |
H30A | 0.1080 | 0.8875 | 0.0905 | 0.286* | |
H30B | 0.0708 | 0.9110 | −0.0171 | 0.286* | |
H30C | 0.0650 | 0.8295 | 0.0089 | 0.286* | |
C31 | 0.38257 (17) | −0.01054 (13) | 0.17998 (17) | 0.0562 (6) | |
H31 | 0.4245 | −0.0271 | 0.2400 | 0.067* | |
C32 | 0.1190 (2) | 0.47937 (19) | −0.1722 (2) | 0.0876 (10) | |
C33 | 0.1057 (3) | 0.5574 (2) | −0.1856 (3) | 0.1069 (13) | |
H33 | 0.0996 | 0.5790 | −0.2423 | 0.128* | |
C34 | 0.1024 (2) | 0.5978 (2) | −0.1147 (3) | 0.1032 (12) | |
H34 | 0.0940 | 0.6477 | −0.1233 | 0.124* | |
C35 | 0.1111 (2) | 0.56769 (17) | −0.0302 (3) | 0.0835 (9) | |
C36 | 0.1091 (2) | 0.60876 (17) | 0.0469 (3) | 0.0931 (11) | |
H36 | 0.1003 | 0.6588 | 0.0405 | 0.112* | |
C37 | 0.1196 (2) | 0.5759 (2) | 0.1291 (3) | 0.0972 (11) | |
H37 | 0.1198 | 0.6042 | 0.1790 | 0.117* | |
C38 | 0.13028 (18) | 0.50068 (17) | 0.1414 (2) | 0.0748 (8) | |
C39 | 0.1398 (2) | 0.4645 (2) | 0.2233 (2) | 0.0897 (10) | |
H39 | 0.1403 | 0.4911 | 0.2747 | 0.108* | |
C40 | 0.1484 (2) | 0.3919 (2) | 0.2308 (2) | 0.0904 (10) | |
H40 | 0.1557 | 0.3686 | 0.2869 | 0.108* | |
C41 | 0.14627 (19) | 0.35185 (19) | 0.1528 (2) | 0.0733 (8) | |
C42 | 0.13143 (16) | 0.45694 (15) | 0.06545 (19) | 0.0619 (6) | |
C43 | 0.12330 (16) | 0.49098 (14) | −0.0211 (2) | 0.0649 (7) | |
C44 | 0.1229 (3) | 0.4319 (2) | −0.2477 (2) | 0.1203 (15) | |
H44A | 0.1516 | 0.3865 | −0.2199 | 0.180* | |
H44B | 0.1587 | 0.4552 | −0.2762 | 0.180* | |
H44C | 0.0608 | 0.4232 | −0.2959 | 0.180* | |
C45 | 0.1509 (3) | 0.27153 (19) | 0.1570 (3) | 0.0997 (11) | |
H45A | 0.0889 | 0.2520 | 0.1302 | 0.150* | |
H45B | 0.1836 | 0.2562 | 0.2225 | 0.150* | |
H45C | 0.1832 | 0.2543 | 0.1211 | 0.150* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.0449 (2) | 0.0421 (2) | 0.0498 (2) | −0.00200 (14) | 0.01706 (16) | −0.00229 (14) |
O1 | 0.0475 (9) | 0.0748 (11) | 0.0512 (10) | 0.0047 (8) | 0.0131 (8) | −0.0028 (8) |
O2 | 0.0491 (9) | 0.0756 (12) | 0.0551 (10) | 0.0016 (8) | 0.0189 (8) | −0.0130 (8) |
O3 | 0.0675 (13) | 0.1065 (16) | 0.1183 (18) | 0.0300 (13) | 0.0461 (13) | 0.0013 (16) |
O4 | 0.0667 (11) | 0.0482 (9) | 0.0594 (10) | −0.0117 (8) | 0.0157 (8) | −0.0055 (8) |
O5 | 0.0697 (12) | 0.0508 (10) | 0.0739 (12) | −0.0078 (8) | 0.0099 (10) | 0.0021 (9) |
O6 | 0.0917 (14) | 0.0484 (10) | 0.0559 (10) | −0.0067 (9) | 0.0141 (10) | 0.0064 (8) |
O7 | 0.0510 (10) | 0.0485 (9) | 0.0821 (12) | −0.0015 (7) | 0.0087 (9) | −0.0013 (9) |
O8 | 0.1011 (19) | 0.152 (3) | 0.121 (2) | −0.007 (2) | 0.0372 (18) | 0.0329 (19) |
O9 | 0.0689 (14) | 0.0969 (17) | 0.152 (2) | 0.0177 (12) | 0.0154 (14) | 0.0402 (16) |
N1 | 0.0447 (10) | 0.0469 (11) | 0.0511 (11) | −0.0005 (8) | 0.0189 (8) | −0.0008 (8) |
N2 | 0.0423 (10) | 0.0448 (10) | 0.0553 (11) | −0.0017 (8) | 0.0157 (9) | 0.0064 (9) |
N3 | 0.0536 (12) | 0.0656 (14) | 0.0652 (14) | 0.0015 (10) | 0.0210 (10) | −0.0015 (11) |
N4 | 0.0671 (14) | 0.0637 (14) | 0.0631 (14) | −0.0099 (11) | 0.0147 (11) | 0.0072 (11) |
C1 | 0.0541 (14) | 0.0645 (15) | 0.0503 (13) | −0.0013 (11) | 0.0216 (11) | 0.0020 (12) |
C2 | 0.0698 (17) | 0.084 (2) | 0.0543 (15) | −0.0007 (15) | 0.0293 (13) | 0.0008 (14) |
C3 | 0.0652 (17) | 0.092 (2) | 0.0570 (16) | −0.0001 (15) | 0.0290 (13) | −0.0151 (15) |
C4 | 0.0488 (14) | 0.0654 (16) | 0.0677 (16) | −0.0015 (12) | 0.0230 (12) | −0.0172 (13) |
C5 | 0.0767 (19) | 0.0677 (18) | 0.088 (2) | 0.0037 (15) | 0.0320 (17) | −0.0252 (17) |
C6 | 0.0743 (19) | 0.0497 (16) | 0.110 (3) | 0.0041 (14) | 0.0310 (18) | −0.0211 (17) |
C7 | 0.0511 (14) | 0.0441 (13) | 0.091 (2) | 0.0001 (11) | 0.0224 (13) | 0.0000 (13) |
C8 | 0.0745 (19) | 0.0415 (14) | 0.112 (3) | 0.0009 (13) | 0.0336 (18) | 0.0106 (16) |
C9 | 0.0734 (19) | 0.0582 (16) | 0.096 (2) | 0.0009 (14) | 0.0325 (17) | 0.0298 (16) |
C10 | 0.0486 (14) | 0.0578 (15) | 0.0681 (16) | −0.0047 (11) | 0.0209 (12) | 0.0144 (12) |
C11 | 0.0376 (11) | 0.0433 (12) | 0.0651 (15) | −0.0009 (9) | 0.0163 (10) | −0.0034 (11) |
C12 | 0.0384 (11) | 0.0501 (13) | 0.0582 (14) | −0.0007 (9) | 0.0193 (10) | −0.0039 (11) |
C13 | 0.106 (2) | 0.0619 (17) | 0.0565 (16) | −0.0002 (16) | 0.0252 (16) | 0.0108 (13) |
C14 | 0.0815 (19) | 0.082 (2) | 0.0679 (17) | −0.0070 (15) | 0.0350 (15) | 0.0170 (15) |
C15 | 0.0478 (12) | 0.0379 (11) | 0.0511 (13) | −0.0042 (9) | 0.0181 (11) | −0.0004 (10) |
C16 | 0.0450 (12) | 0.0342 (10) | 0.0534 (13) | 0.0009 (9) | 0.0192 (10) | 0.0027 (9) |
C17 | 0.0583 (14) | 0.0440 (12) | 0.0543 (13) | 0.0004 (11) | 0.0211 (11) | 0.0001 (10) |
C18 | 0.0687 (17) | 0.0527 (14) | 0.0728 (17) | 0.0059 (12) | 0.0371 (14) | −0.0039 (12) |
C19 | 0.0580 (15) | 0.0484 (14) | 0.091 (2) | 0.0105 (11) | 0.0376 (15) | 0.0046 (13) |
C20 | 0.0498 (14) | 0.0663 (16) | 0.0677 (16) | 0.0074 (12) | 0.0151 (12) | 0.0011 (13) |
C21 | 0.0523 (14) | 0.0594 (15) | 0.0564 (14) | 0.0057 (11) | 0.0209 (12) | −0.0020 (11) |
C22 | 0.0587 (15) | 0.0498 (13) | 0.0542 (14) | −0.0062 (11) | 0.0244 (12) | −0.0037 (11) |
C23 | 0.0533 (13) | 0.0465 (12) | 0.0498 (13) | −0.0086 (10) | 0.0217 (11) | −0.0028 (10) |
C24 | 0.0778 (18) | 0.0542 (15) | 0.0459 (13) | −0.0120 (13) | 0.0083 (12) | 0.0080 (11) |
C25 | 0.0867 (19) | 0.0488 (14) | 0.0475 (14) | −0.0189 (13) | 0.0097 (13) | 0.0001 (11) |
C26 | 0.0605 (14) | 0.0480 (13) | 0.0501 (13) | −0.0067 (11) | 0.0221 (11) | 0.0034 (10) |
C28 | 0.0501 (13) | 0.0544 (14) | 0.0551 (14) | −0.0054 (11) | 0.0159 (11) | −0.0126 (11) |
C29 | 0.127 (4) | 0.174 (5) | 0.146 (4) | −0.019 (3) | 0.055 (3) | 0.049 (4) |
C30 | 0.124 (4) | 0.311 (9) | 0.161 (5) | 0.017 (5) | 0.085 (4) | 0.056 (5) |
C31 | 0.0514 (13) | 0.0585 (15) | 0.0485 (13) | 0.0010 (11) | 0.0118 (11) | 0.0001 (11) |
C32 | 0.084 (2) | 0.089 (2) | 0.071 (2) | −0.0223 (17) | 0.0150 (16) | 0.0118 (17) |
C33 | 0.103 (3) | 0.098 (3) | 0.094 (3) | −0.013 (2) | 0.019 (2) | 0.039 (2) |
C34 | 0.085 (2) | 0.075 (2) | 0.121 (3) | −0.0080 (18) | 0.019 (2) | 0.024 (2) |
C35 | 0.0578 (17) | 0.0647 (18) | 0.106 (2) | −0.0042 (14) | 0.0153 (16) | 0.0041 (18) |
C36 | 0.0678 (19) | 0.0547 (17) | 0.140 (3) | 0.0021 (14) | 0.029 (2) | −0.024 (2) |
C37 | 0.076 (2) | 0.089 (3) | 0.118 (3) | 0.0023 (18) | 0.033 (2) | −0.028 (2) |
C38 | 0.0488 (15) | 0.078 (2) | 0.087 (2) | −0.0008 (13) | 0.0194 (14) | −0.0221 (17) |
C39 | 0.077 (2) | 0.118 (3) | 0.078 (2) | 0.000 (2) | 0.0366 (17) | −0.020 (2) |
C40 | 0.082 (2) | 0.121 (3) | 0.072 (2) | −0.005 (2) | 0.0371 (17) | −0.003 (2) |
C41 | 0.0592 (16) | 0.098 (2) | 0.0610 (17) | 0.0005 (15) | 0.0243 (13) | 0.0014 (16) |
C42 | 0.0422 (13) | 0.0677 (17) | 0.0675 (16) | −0.0010 (11) | 0.0158 (12) | −0.0076 (13) |
C43 | 0.0439 (13) | 0.0505 (14) | 0.0835 (19) | −0.0032 (11) | 0.0115 (13) | −0.0078 (13) |
C44 | 0.149 (4) | 0.138 (4) | 0.068 (2) | −0.033 (3) | 0.041 (2) | 0.009 (2) |
C45 | 0.119 (3) | 0.093 (2) | 0.093 (2) | 0.009 (2) | 0.051 (2) | 0.0252 (19) |
Mn1—O4 | 2.1413 (17) | C15—C16 | 1.492 (3) |
Mn1—O7 | 2.1562 (17) | C16—C17 | 1.383 (3) |
Mn1—O1 | 2.2277 (17) | C16—C21 | 1.388 (3) |
Mn1—N1 | 2.2755 (18) | C17—C18 | 1.378 (3) |
Mn1—N2 | 2.2974 (18) | C17—H17 | 0.9300 |
Mn1—O2 | 2.3258 (16) | C18—C19 | 1.376 (4) |
Mn1—C15 | 2.630 (2) | C18—H18 | 0.9300 |
O1—C15 | 1.249 (3) | C19—C20 | 1.382 (4) |
O2—C15 | 1.265 (3) | C20—C21 | 1.372 (3) |
O3—C19 | 1.370 (3) | C20—H20 | 0.9300 |
O3—H3 | 0.8200 | C21—H21 | 0.9300 |
O4—C22 | 1.262 (3) | C22—C23 | 1.494 (3) |
O5—C22 | 1.258 (3) | C23—C28 | 1.382 (3) |
O6—C26 | 1.355 (3) | C23—C24 | 1.385 (3) |
O6—H6 | 0.8200 | C24—C25 | 1.378 (3) |
O7—H1W | 0.8200 | C24—H24 | 0.9300 |
O7—H2W | 0.8363 | C25—C26 | 1.387 (3) |
O8—C29 | 1.415 (5) | C25—H25 | 0.9300 |
O8—H8 | 0.8200 | C26—C31 | 1.380 (3) |
O9—H3W | 0.8460 | C28—C31 | 1.381 (3) |
O9—H4W | 0.8418 | C28—H28 | 0.9300 |
N1—C1 | 1.341 (3) | C29—C30 | 1.436 (7) |
N1—C12 | 1.366 (3) | C29—H29A | 0.9700 |
N2—C10 | 1.334 (3) | C29—H29B | 0.9700 |
N2—C11 | 1.371 (3) | C30—H30A | 0.9600 |
N3—C41 | 1.340 (3) | C30—H30B | 0.9600 |
N3—C42 | 1.344 (3) | C30—H30C | 0.9600 |
N4—C32 | 1.316 (4) | C31—H31 | 0.9300 |
N4—C43 | 1.363 (3) | C32—C33 | 1.453 (5) |
C1—C2 | 1.404 (4) | C32—C44 | 1.481 (5) |
C1—C13 | 1.484 (4) | C33—C34 | 1.346 (5) |
C2—C3 | 1.352 (4) | C33—H33 | 0.9300 |
C2—H2 | 0.9300 | C34—C35 | 1.371 (5) |
C3—C4 | 1.404 (4) | C34—H34 | 0.9300 |
C3—H3A | 0.9300 | C35—C36 | 1.424 (5) |
C4—C12 | 1.410 (3) | C35—C43 | 1.424 (4) |
C4—C5 | 1.426 (4) | C36—C37 | 1.353 (5) |
C5—C6 | 1.337 (4) | C36—H36 | 0.9300 |
C5—H5 | 0.9300 | C37—C38 | 1.398 (5) |
C6—C7 | 1.433 (4) | C37—H37 | 0.9300 |
C6—H6A | 0.9300 | C38—C39 | 1.381 (5) |
C7—C8 | 1.397 (4) | C38—C42 | 1.432 (4) |
C7—C11 | 1.411 (3) | C39—C40 | 1.344 (5) |
C8—C9 | 1.353 (4) | C39—H39 | 0.9300 |
C8—H8A | 0.9300 | C40—C41 | 1.402 (4) |
C9—C10 | 1.413 (4) | C40—H40 | 0.9300 |
C9—H9 | 0.9300 | C41—C45 | 1.481 (5) |
C10—C14 | 1.495 (4) | C42—C43 | 1.433 (4) |
C11—C12 | 1.439 (3) | C44—H44A | 0.9600 |
C13—H13A | 0.9600 | C44—H44B | 0.9600 |
C13—H13B | 0.9600 | C44—H44C | 0.9600 |
C13—H13C | 0.9600 | C45—H45A | 0.9600 |
C14—H14A | 0.9600 | C45—H45B | 0.9600 |
C14—H14B | 0.9600 | C45—H45C | 0.9600 |
C14—H14C | 0.9600 | ||
O4—Mn1—O7 | 84.88 (6) | C18—C17—C16 | 121.3 (2) |
O4—Mn1—O1 | 90.19 (7) | C18—C17—H17 | 119.4 |
O7—Mn1—O1 | 100.72 (7) | C16—C17—H17 | 119.4 |
O4—Mn1—N1 | 103.49 (7) | C19—C18—C17 | 119.6 (2) |
O7—Mn1—N1 | 120.85 (7) | C19—C18—H18 | 120.2 |
O1—Mn1—N1 | 136.89 (6) | C17—C18—H18 | 120.2 |
O4—Mn1—N2 | 163.62 (7) | O3—C19—C18 | 118.1 (3) |
O7—Mn1—N2 | 82.86 (6) | O3—C19—C20 | 122.0 (3) |
O1—Mn1—N2 | 102.72 (7) | C18—C19—C20 | 119.9 (2) |
N1—Mn1—N2 | 73.95 (7) | C21—C20—C19 | 120.0 (2) |
O4—Mn1—O2 | 98.32 (6) | C21—C20—H20 | 120.0 |
O7—Mn1—O2 | 157.25 (7) | C19—C20—H20 | 120.0 |
O1—Mn1—O2 | 56.93 (6) | C20—C21—C16 | 120.9 (2) |
N1—Mn1—O2 | 80.51 (6) | C20—C21—H21 | 119.6 |
N2—Mn1—O2 | 97.18 (6) | C16—C21—H21 | 119.6 |
O4—Mn1—C15 | 93.01 (7) | O5—C22—O4 | 124.2 (2) |
O7—Mn1—C15 | 128.99 (7) | O5—C22—C23 | 118.0 (2) |
O1—Mn1—C15 | 28.28 (6) | O4—C22—C23 | 117.7 (2) |
N1—Mn1—C15 | 109.21 (7) | C28—C23—C24 | 117.4 (2) |
N2—Mn1—C15 | 103.14 (7) | C28—C23—C22 | 122.4 (2) |
O2—Mn1—C15 | 28.76 (6) | C24—C23—C22 | 120.1 (2) |
C15—O1—Mn1 | 94.06 (14) | C25—C24—C23 | 121.8 (2) |
C15—O2—Mn1 | 89.08 (13) | C25—C24—H24 | 119.1 |
C19—O3—H3 | 109.5 | C23—C24—H24 | 119.1 |
C22—O4—Mn1 | 135.11 (16) | C24—C25—C26 | 119.9 (2) |
C26—O6—H6 | 109.5 | C24—C25—H25 | 120.0 |
Mn1—O7—H1W | 109.5 | C26—C25—H25 | 120.0 |
Mn1—O7—H2W | 115.4 | O6—C26—C31 | 123.6 (2) |
H1W—O7—H2W | 110.7 | O6—C26—C25 | 117.5 (2) |
C29—O8—H8 | 109.5 | C31—C26—C25 | 118.9 (2) |
H3W—O9—H4W | 107.1 | C31—C28—C23 | 121.5 (2) |
C1—N1—C12 | 118.7 (2) | C31—C28—H28 | 119.3 |
C1—N1—Mn1 | 126.04 (15) | C23—C28—H28 | 119.3 |
C12—N1—Mn1 | 114.80 (14) | O8—C29—C30 | 111.9 (5) |
C10—N2—C11 | 119.0 (2) | O8—C29—H29A | 109.2 |
C10—N2—Mn1 | 127.01 (17) | C30—C29—H29A | 109.2 |
C11—N2—Mn1 | 113.86 (14) | O8—C29—H29B | 109.2 |
C41—N3—C42 | 119.1 (2) | C30—C29—H29B | 109.2 |
C32—N4—C43 | 119.9 (3) | H29A—C29—H29B | 107.9 |
N1—C1—C2 | 121.4 (2) | C29—C30—H30A | 109.5 |
N1—C1—C13 | 119.0 (2) | C29—C30—H30B | 109.5 |
C2—C1—C13 | 119.7 (2) | H30A—C30—H30B | 109.5 |
C3—C2—C1 | 120.4 (3) | C29—C30—H30C | 109.5 |
C3—C2—H2 | 119.8 | H30A—C30—H30C | 109.5 |
C1—C2—H2 | 119.8 | H30B—C30—H30C | 109.5 |
C2—C3—C4 | 119.9 (2) | C26—C31—C28 | 120.3 (2) |
C2—C3—H3A | 120.1 | C26—C31—H31 | 119.8 |
C4—C3—H3A | 120.1 | C28—C31—H31 | 119.8 |
C3—C4—C12 | 117.4 (2) | N4—C32—C33 | 120.1 (3) |
C3—C4—C5 | 122.6 (3) | N4—C32—C44 | 118.3 (3) |
C12—C4—C5 | 120.0 (3) | C33—C32—C44 | 121.6 (3) |
C6—C5—C4 | 120.8 (3) | C34—C33—C32 | 119.0 (3) |
C6—C5—H5 | 119.6 | C34—C33—H33 | 120.5 |
C4—C5—H5 | 119.6 | C32—C33—H33 | 120.5 |
C5—C6—C7 | 121.4 (3) | C33—C34—C35 | 122.1 (4) |
C5—C6—H6A | 119.3 | C33—C34—H34 | 118.9 |
C7—C6—H6A | 119.3 | C35—C34—H34 | 118.9 |
C8—C7—C11 | 117.1 (3) | C34—C35—C36 | 123.7 (4) |
C8—C7—C6 | 123.4 (3) | C34—C35—C43 | 116.6 (3) |
C11—C7—C6 | 119.5 (3) | C36—C35—C43 | 119.7 (3) |
C9—C8—C7 | 120.3 (3) | C37—C36—C35 | 120.8 (3) |
C9—C8—H8A | 119.9 | C37—C36—H36 | 119.6 |
C7—C8—H8A | 119.9 | C35—C36—H36 | 119.6 |
C8—C9—C10 | 120.4 (3) | C36—C37—C38 | 122.0 (3) |
C8—C9—H9 | 119.8 | C36—C37—H37 | 119.0 |
C10—C9—H9 | 119.8 | C38—C37—H37 | 119.0 |
N2—C10—C9 | 120.8 (3) | C39—C38—C37 | 124.2 (3) |
N2—C10—C14 | 118.6 (2) | C39—C38—C42 | 116.6 (3) |
C9—C10—C14 | 120.6 (2) | C37—C38—C42 | 119.3 (3) |
N2—C11—C7 | 122.3 (2) | C40—C39—C38 | 121.7 (3) |
N2—C11—C12 | 118.51 (19) | C40—C39—H39 | 119.2 |
C7—C11—C12 | 119.1 (2) | C38—C39—H39 | 119.2 |
N1—C12—C4 | 122.2 (2) | C39—C40—C41 | 119.1 (3) |
N1—C12—C11 | 118.6 (2) | C39—C40—H40 | 120.5 |
C4—C12—C11 | 119.1 (2) | C41—C40—H40 | 120.5 |
C1—C13—H13A | 109.5 | N3—C41—C40 | 121.7 (3) |
C1—C13—H13B | 109.5 | N3—C41—C45 | 117.9 (3) |
H13A—C13—H13B | 109.5 | C40—C41—C45 | 120.4 (3) |
C1—C13—H13C | 109.5 | N3—C42—C38 | 121.8 (3) |
H13A—C13—H13C | 109.5 | N3—C42—C43 | 118.6 (2) |
H13B—C13—H13C | 109.5 | C38—C42—C43 | 119.6 (3) |
C10—C14—H14A | 109.5 | N4—C43—C35 | 122.2 (3) |
C10—C14—H14B | 109.5 | N4—C43—C42 | 119.1 (2) |
H14A—C14—H14B | 109.5 | C35—C43—C42 | 118.6 (3) |
C10—C14—H14C | 109.5 | C32—C44—H44A | 109.5 |
H14A—C14—H14C | 109.5 | C32—C44—H44B | 109.5 |
H14B—C14—H14C | 109.5 | H44A—C44—H44B | 109.5 |
O1—C15—O2 | 119.5 (2) | C32—C44—H44C | 109.5 |
O1—C15—C16 | 120.3 (2) | H44A—C44—H44C | 109.5 |
O2—C15—C16 | 120.2 (2) | H44B—C44—H44C | 109.5 |
O1—C15—Mn1 | 57.67 (12) | C41—C45—H45A | 109.5 |
O2—C15—Mn1 | 62.16 (12) | C41—C45—H45B | 109.5 |
C16—C15—Mn1 | 172.95 (15) | H45A—C45—H45B | 109.5 |
C17—C16—C21 | 118.2 (2) | C41—C45—H45C | 109.5 |
C17—C16—C15 | 120.5 (2) | H45A—C45—H45C | 109.5 |
C21—C16—C15 | 121.2 (2) | H45B—C45—H45C | 109.5 |
O4—Mn1—O1—C15 | −96.01 (14) | N2—C11—C12—C4 | 172.7 (2) |
O7—Mn1—O1—C15 | 179.17 (13) | C7—C11—C12—C4 | −4.2 (3) |
N1—Mn1—O1—C15 | 14.16 (18) | Mn1—O1—C15—O2 | −6.8 (2) |
N2—Mn1—O1—C15 | 94.16 (14) | Mn1—O1—C15—C16 | 172.09 (17) |
O2—Mn1—O1—C15 | 3.81 (12) | Mn1—O2—C15—O1 | 6.5 (2) |
O4—Mn1—O2—C15 | 81.01 (14) | Mn1—O2—C15—C16 | −172.40 (17) |
O7—Mn1—O2—C15 | −15.6 (2) | O4—Mn1—C15—O1 | 84.79 (14) |
O1—Mn1—O2—C15 | −3.75 (12) | O7—Mn1—C15—O1 | −1.05 (17) |
N1—Mn1—O2—C15 | −176.60 (14) | N1—Mn1—C15—O1 | −169.81 (13) |
N2—Mn1—O2—C15 | −104.28 (13) | N2—Mn1—C15—O1 | −92.48 (14) |
O7—Mn1—O4—C22 | 2.1 (2) | O2—Mn1—C15—O1 | −173.4 (2) |
O1—Mn1—O4—C22 | −98.6 (2) | O4—Mn1—C15—O2 | −101.86 (13) |
N1—Mn1—O4—C22 | 122.7 (2) | O7—Mn1—C15—O2 | 172.30 (12) |
N2—Mn1—O4—C22 | 43.8 (4) | O1—Mn1—C15—O2 | 173.4 (2) |
O2—Mn1—O4—C22 | −155.2 (2) | N1—Mn1—C15—O2 | 3.55 (14) |
C15—Mn1—O4—C22 | −126.8 (2) | N2—Mn1—C15—O2 | 80.88 (14) |
O4—Mn1—N1—C1 | 25.45 (19) | O1—C15—C16—C17 | −5.9 (3) |
O7—Mn1—N1—C1 | 117.53 (18) | O2—C15—C16—C17 | 172.9 (2) |
O1—Mn1—N1—C1 | −79.7 (2) | O1—C15—C16—C21 | 175.3 (2) |
N2—Mn1—N1—C1 | −171.29 (19) | O2—C15—C16—C21 | −5.9 (3) |
O2—Mn1—N1—C1 | −70.91 (18) | C21—C16—C17—C18 | −0.3 (3) |
C15—Mn1—N1—C1 | −72.64 (19) | C15—C16—C17—C18 | −179.1 (2) |
O4—Mn1—N1—C12 | −162.76 (14) | C16—C17—C18—C19 | 1.3 (4) |
O7—Mn1—N1—C12 | −70.68 (16) | C17—C18—C19—O3 | 179.1 (2) |
O1—Mn1—N1—C12 | 92.10 (16) | C17—C18—C19—C20 | −1.8 (4) |
N2—Mn1—N1—C12 | 0.51 (14) | O3—C19—C20—C21 | −179.7 (3) |
O2—Mn1—N1—C12 | 100.88 (15) | C18—C19—C20—C21 | 1.2 (4) |
C15—Mn1—N1—C12 | 99.15 (15) | C19—C20—C21—C16 | −0.2 (4) |
O4—Mn1—N2—C10 | −95.8 (3) | C17—C16—C21—C20 | −0.3 (3) |
O7—Mn1—N2—C10 | −53.96 (18) | C15—C16—C21—C20 | 178.5 (2) |
O1—Mn1—N2—C10 | 45.47 (19) | Mn1—O4—C22—O5 | −4.5 (4) |
N1—Mn1—N2—C10 | −178.98 (19) | Mn1—O4—C22—C23 | 173.87 (16) |
O2—Mn1—N2—C10 | 103.10 (18) | O5—C22—C23—C28 | −169.7 (2) |
C15—Mn1—N2—C10 | 74.50 (19) | O4—C22—C23—C28 | 11.8 (4) |
O4—Mn1—N2—C11 | 79.9 (3) | O5—C22—C23—C24 | 13.7 (4) |
O7—Mn1—N2—C11 | 121.72 (15) | O4—C22—C23—C24 | −164.8 (2) |
O1—Mn1—N2—C11 | −138.85 (14) | C28—C23—C24—C25 | −1.9 (4) |
N1—Mn1—N2—C11 | −3.30 (14) | C22—C23—C24—C25 | 174.9 (3) |
O2—Mn1—N2—C11 | −81.22 (14) | C23—C24—C25—C26 | 1.4 (4) |
C15—Mn1—N2—C11 | −109.82 (15) | C24—C25—C26—O6 | −178.7 (3) |
C12—N1—C1—C2 | 1.1 (3) | C24—C25—C26—C31 | 0.9 (4) |
Mn1—N1—C1—C2 | 172.65 (18) | C24—C23—C28—C31 | 0.1 (4) |
C12—N1—C1—C13 | −178.0 (2) | C22—C23—C28—C31 | −176.6 (2) |
Mn1—N1—C1—C13 | −6.5 (3) | O6—C26—C31—C28 | 176.9 (2) |
N1—C1—C2—C3 | 0.9 (4) | C25—C26—C31—C28 | −2.6 (4) |
C13—C1—C2—C3 | −179.9 (3) | C23—C28—C31—C26 | 2.2 (4) |
C1—C2—C3—C4 | −0.7 (4) | C43—N4—C32—C33 | 1.0 (4) |
C2—C3—C4—C12 | −1.4 (4) | C43—N4—C32—C44 | −178.9 (3) |
C2—C3—C4—C5 | 179.6 (3) | N4—C32—C33—C34 | −0.2 (5) |
C3—C4—C5—C6 | 177.4 (3) | C44—C32—C33—C34 | 179.7 (4) |
C12—C4—C5—C6 | −1.6 (4) | C32—C33—C34—C35 | −0.1 (6) |
C4—C5—C6—C7 | −1.4 (5) | C33—C34—C35—C36 | 179.3 (3) |
C5—C6—C7—C8 | −176.8 (3) | C33—C34—C35—C43 | −0.4 (5) |
C5—C6—C7—C11 | 1.6 (4) | C34—C35—C36—C37 | −178.9 (3) |
C11—C7—C8—C9 | −1.9 (4) | C43—C35—C36—C37 | 0.8 (5) |
C6—C7—C8—C9 | 176.5 (3) | C35—C36—C37—C38 | −1.9 (5) |
C7—C8—C9—C10 | −0.5 (4) | C36—C37—C38—C39 | −179.0 (3) |
C11—N2—C10—C9 | −1.2 (3) | C36—C37—C38—C42 | 0.9 (5) |
Mn1—N2—C10—C9 | 174.27 (18) | C37—C38—C39—C40 | 178.9 (3) |
C11—N2—C10—C14 | 177.6 (2) | C42—C38—C39—C40 | −0.9 (5) |
Mn1—N2—C10—C14 | −6.9 (3) | C38—C39—C40—C41 | −0.9 (5) |
C8—C9—C10—N2 | 2.2 (4) | C42—N3—C41—C40 | −1.1 (4) |
C8—C9—C10—C14 | −176.6 (3) | C42—N3—C41—C45 | 177.9 (3) |
C10—N2—C11—C7 | −1.4 (3) | C39—C40—C41—N3 | 2.0 (5) |
Mn1—N2—C11—C7 | −177.44 (17) | C39—C40—C41—C45 | −177.0 (3) |
C10—N2—C11—C12 | −178.2 (2) | C41—N3—C42—C38 | −0.9 (4) |
Mn1—N2—C11—C12 | 5.7 (2) | C41—N3—C42—C43 | −180.0 (2) |
C8—C7—C11—N2 | 2.9 (3) | C39—C38—C42—N3 | 1.9 (4) |
C6—C7—C11—N2 | −175.5 (2) | C37—C38—C42—N3 | −178.0 (3) |
C8—C7—C11—C12 | 179.7 (2) | C39—C38—C42—C43 | −179.0 (2) |
C6—C7—C11—C12 | 1.3 (3) | C37—C38—C42—C43 | 1.1 (4) |
C1—N1—C12—C4 | −3.5 (3) | C32—N4—C43—C35 | −1.6 (4) |
Mn1—N1—C12—C4 | −175.89 (17) | C32—N4—C43—C42 | 178.8 (2) |
C1—N1—C12—C11 | 174.7 (2) | C34—C35—C43—N4 | 1.2 (4) |
Mn1—N1—C12—C11 | 2.3 (2) | C36—C35—C43—N4 | −178.5 (3) |
C3—C4—C12—N1 | 3.6 (3) | C34—C35—C43—C42 | −179.2 (3) |
C5—C4—C12—N1 | −177.4 (2) | C36—C35—C43—C42 | 1.2 (4) |
C3—C4—C12—C11 | −174.6 (2) | N3—C42—C43—N4 | −3.3 (3) |
C5—C4—C12—C11 | 4.4 (3) | C38—C42—C43—N4 | 177.6 (2) |
N2—C11—C12—N1 | −5.6 (3) | N3—C42—C43—C35 | 177.0 (2) |
C7—C11—C12—N1 | 177.5 (2) | C38—C42—C43—C35 | −2.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O9i | 0.82 | 1.83 | 2.651 (4) | 176 |
O6—H6···O2ii | 0.82 | 1.83 | 2.640 (2) | 169 |
O7—H1W···O5 | 0.82 | 1.83 | 2.613 (2) | 158 |
O7—H2W···N3 | 0.84 | 2.51 | 3.186 (3) | 139 |
O7—H2W···N4 | 0.84 | 2.24 | 2.998 (3) | 151 |
O8—H8···O5iii | 0.82 | 1.88 | 2.685 (3) | 167 |
O9—H3W···O8iv | 0.85 | 2.03 | 2.727 (4) | 140 |
O9—H4W···N3v | 0.84 | 2.67 | 3.336 (3) | 137 |
O9—H4W···N4v | 0.84 | 2.28 | 3.061 (3) | 155 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+1/2; (iii) −x, −y+1, −z; (iv) −x, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Mn(C7H5O3)2(C14H12N2)(H2O)]·C14H12N2·C2H6O·H2O |
Mr | 827.77 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 297 |
a, b, c (Å) | 15.9080 (12), 18.4137 (14), 15.4744 (11) |
β (°) | 115.585 (1) |
V (Å3) | 4088.4 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.38 |
Crystal size (mm) | 0.48 × 0.35 × 0.29 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.838, 0.896 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 30925, 7614, 5682 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.128, 1.03 |
No. of reflections | 7614 |
No. of parameters | 532 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.34 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
Mn1—O4 | 2.1413 (17) | Mn1—N1 | 2.2755 (18) |
Mn1—O7 | 2.1562 (17) | Mn1—N2 | 2.2974 (18) |
Mn1—O1 | 2.2277 (17) | Mn1—O2 | 2.3258 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O9i | 0.82 | 1.83 | 2.651 (4) | 175.9 |
O6—H6···O2ii | 0.82 | 1.83 | 2.640 (2) | 168.7 |
O7—H1W···O5 | 0.82 | 1.83 | 2.613 (2) | 158.0 |
O7—H2W···N4 | 0.84 | 2.24 | 2.998 (3) | 151.0 |
O8—H8···O5iii | 0.82 | 1.88 | 2.685 (3) | 166.9 |
O9—H4W···N4iv | 0.84 | 2.28 | 3.061 (3) | 155.3 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+1/2; (iii) −x, −y+1, −z; (iv) x, −y+1/2, z+1/2. |
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Crystal structures of MnII complexes of 1,10-phenanthroline or its derivatives combined with benzoic anions have been reported (Pan et al., 2006; Su et al., 2005; Wang et al., 2003; Wang et al., 2004; Xiao, 2005; Yang et al., 2006; Zhang, 2006). Recently, as part of our ongoing studies (Xuan et al., 2007; Zhao et al., 2007) of mixed-ligand complexes, we have reported the structure of MnII complexes (Zhao et al., 2007). In this paper, we present the crystal structure of a MnII complex of 2,9-dimethyl-1,10-phenanthroline (dmphen) and 4-hydroxybenzoate anion, which is not very different to that our previously reported complex, which was obtained by reaction of dmphen, sodium 3-hydroxybenzoate and Mn(NO3)2 aqueous solutions (Xuan et al., 2007).
As shown in Fig. 1, the structure unit of (I) is composed of a MnII complex, [Mn(C7H5O3)2(C14H12N2)(H2O)], one non-coordinated dmphen molecule, one ethanol and one water molecule. Two N atoms from one dmphen ligand, three O atoms from monodentate and bidentate carboxyl groups of two 4-hydroxybenzoate anions, and one O atom from water are coordinated to the MnII ion in a strongly distorted arrangement. The coordination geometry around the metal centre may be described as a distorted square pyramidal arrangement, considering the bidentate benzoate anion placed in the apical position. The corresponding bond lengths are listed in Table 1. Additionally, the non-bonding separation between Mn atom and the carboxyl O atoms of monodentate benzoate anion is 3.520 (3) Å, much larger than the distance expected for a Mn—O bond.
In the crystal structure, the complex is stabilizing by π–π interactions between the free and coordinated dmphen. The centroid (ring C4···C7/C11/C12) to centroid (ring C38···C41/N3/C42) separation is 3.812 (5) Å.
A structural feature of (I) is the extensive network of hydrogen bonds (Table 2 and Fig. 2). The coordinated water participates in hydrogen bonds with the O atom of benzoate and to the N atoms of uncoordinated dmphen molecule. The 4-hydroxybenzoate ligand and the uncoordinated ethanol also form hydrogen bonds with carbonyl O atom of neighboring benzoate and with lattice water molecule.