metal-organic compounds
catena-Poly[[[bis[4-(1H-1,3,7,8-tetraazacyclopenta[l]phenanthren-2-yl)phenol-κ2N7,N8]manganese(II)]-μ-naphthalene-1,4-dicarboxylato-κ2O1:O4] naphthalene-1,4-dicarboxylic acid hemisolvate monohydrate]
aDepartment of Chemistry, Jilin Normal University, Siping 136000, People's Republic of China, bXi'an Modern Chemistry Research Institute, Xi'an 710065, People's Republic of China, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
The 1,4-dicarboxylate dianions in the title compound, [Mn(C12H6O4)(C19H12N4O)2]·0.5C12H8O4·H2O, bond to two 4-(1H-1,3,7,8-tetraazacyclopenta[l]phenanthren-2-yl)phenol-chelated Mn atoms to form a chain that features the metal atom in an octahedral coordination geometry. Adjacent chains interact with the uncoordinated water molecules to form a three-dimensional network. The naphthalene-1,4-dicarboxylic acid solvent molecule, which is disordered about a centre of inversion, occupies the space within the network but is not bonded to the network. One NH group is disordered equally over two positions.
Related literature
There are several studies of (2-phenyl-1H-1,3,7,8,-tetraazacyclopenta[l]phenanthrene-chelated manganese dicarboxylates (see, for example, Li et al., 2008). The 4-hydroxy-substituted N-heterocycle forms an adduct with manganese(II) terephthalate (see Che et al., 2006).
Experimental
Crystal data
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Refinement
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Data collection: RAPID-AUTO (Rigaku, 1998); cell RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003); software used to prepare material for publication: publCIF (Westrip, 2008).
Supporting information
10.1107/S160053680801074X/bx2132sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053680801074X/bx2132Isup2.hkl
Manganese dichloride dihydrate (0.02 g, 0.1 mmol), naphthalene-1,4-dicarboxylic acid (0.02 g, 0.1 mmol), 4-(1H-1,3,7,8-tetraazacyclopenta[l]phenanthren-2-yl)phenol4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol (0.03 g, 0.1 mmol) and water (15 ml) were heated in a 23 ml, Teflon-lined, stainless-steel Parr bomb at 408 K for 2 days. Crystals were obtained in 40% yield.
The naphthalene-1,4-dicarboxylic acid is disordered over a center-of-inversion. The fused-ring portion was refined as a rigid naphthalene group of 1.39 Å sides; the occupancy is 0.5. The C–O distances were restrained to 1.25±0.01 Å and the Ccarboxyl–Caryl distances to 1.50±0.01 Å. Other restrained were applied to the carboxyl parts. The anisotropic displacement factors of the carbon and oxygen atoms were restrained to be nearly isotropic. The acid H atoms were arbitrarily placed on the carboxyl parts.
The carbon- and nitrogen-bound H atoms were placed in calculated positions [C–H 0.93, N–H 0.86, O–H 0.82 Å and Uiso(H) 1.2Ueq(C,N,O)], and were included in the
in the riding-model approximation. For one of the N-heterocycles, the amino –NH group is ordered whereas for the other, it is disordered. For the second N-heterocycle, hydrogen atoms of 0.5 occupancy were placed on the two nitrogen atoms. The water H-atoms were placed in chemically sensible positions on the basis of hydrogen bonds.The final difference Fourier map had a large peak near H14, but this could not be modeled as a water molecule.
Data collection: RAPID-AUTO (Rigaku, 1998); cell
RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003); software used to prepare material for publication: publCIF (Westrip, 2008).Fig. 1. Thermal ellipsoid plot of Mn(C19H12N4O)2(C12H6O4).(C12H8O4)0.5.H2O; displacement ellipsoids are drawn at the 50% probability level, and H atoms as spheres of arbitrary radius. The naphthalene-1,4-dicarboxylic acid is disordered about a center-of-inversion. [Symmetry code i: x, 1 - y, 1/2 + z]. | |
Fig. 2. Chain structure of the manganese-naphthalene-1,4-dicarboxylate network as illustrated by OLEX (Dolomanov et al., 2003). |
[Mn(C12H6O4)(C19H12N4O)2]·0.5C12H8O4·H2O | F(000) = 4200 |
Mr = 1019.87 | Dx = 1.536 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 24704 reflections |
a = 48.398 (15) Å | θ = 3.0–27.5° |
b = 9.089 (2) Å | µ = 0.38 mm−1 |
c = 20.598 (6) Å | T = 295 K |
β = 103.20 (1)° | Block, brown |
V = 8821 (4) Å3 | 0.31 × 0.25 × 0.18 mm |
Z = 8 |
Rigaku R-AXIS RAPID diffractometer | 10014 independent reflections |
Radiation source: fine-focus sealed tube | 5868 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.084 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ω scans | h = −62→62 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −11→11 |
Tmin = 0.820, Tmax = 1.000 | l = −25→26 |
40785 measured reflections |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0782P)2 + 7.7802P] where P = (Fo2 + 2Fc2)/3 |
10014 reflections | (Δ/σ)max = 0.001 |
717 parameters | Δρmax = 1.35 e Å−3 |
116 restraints | Δρmin = −0.42 e Å−3 |
[Mn(C12H6O4)(C19H12N4O)2]·0.5C12H8O4·H2O | V = 8821 (4) Å3 |
Mr = 1019.87 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 48.398 (15) Å | µ = 0.38 mm−1 |
b = 9.089 (2) Å | T = 295 K |
c = 20.598 (6) Å | 0.31 × 0.25 × 0.18 mm |
β = 103.20 (1)° |
Rigaku R-AXIS RAPID diffractometer | 10014 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 5868 reflections with I > 2σ(I) |
Tmin = 0.820, Tmax = 1.000 | Rint = 0.084 |
40785 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 116 restraints |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.03 | Δρmax = 1.35 e Å−3 |
10014 reflections | Δρmin = −0.42 e Å−3 |
717 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Mn1 | 0.648562 (11) | 0.41289 (6) | 0.51035 (2) | 0.03142 (15) | |
O1 | 0.66266 (5) | 0.5844 (3) | 0.45399 (11) | 0.0379 (6) | |
O2 | 0.70748 (5) | 0.5903 (3) | 0.44417 (12) | 0.0468 (7) | |
O3 | 0.65765 (6) | 0.4702 (3) | 0.10116 (11) | 0.0487 (7) | |
O4 | 0.62358 (12) | 0.3337 (5) | 0.12178 (16) | 0.137 (2) | |
O5 | 0.80478 (5) | −0.5497 (3) | 0.28409 (12) | 0.0431 (6) | |
H5O | 0.7975 | −0.5713 | 0.2453 | 0.052* | |
O6 | 0.39480 (6) | 0.0139 (4) | 0.56796 (15) | 0.0580 (8) | |
H6O | 0.3828 | 0.0538 | 0.5388 | 0.070* | |
O1W | 0.64402 (6) | 0.8246 (3) | 0.51341 (13) | 0.0585 (8) | |
H1W1 | 0.6381 | 0.7882 | 0.5440 | 0.070* | |
H1W2 | 0.6500 | 0.7580 | 0.4935 | 0.070* | |
N1 | 0.64987 (6) | 0.2597 (3) | 0.42332 (13) | 0.0329 (6) | |
N2 | 0.71343 (6) | −0.0949 (3) | 0.35027 (13) | 0.0326 (6) | |
N3 | 0.74551 (6) | −0.0806 (3) | 0.44653 (13) | 0.0323 (6) | |
H3N | 0.7608 | −0.0958 | 0.4765 | 0.039* | |
N4 | 0.68967 (6) | 0.2888 (3) | 0.53848 (13) | 0.0323 (6) | |
N5 | 0.60125 (6) | 0.4417 (3) | 0.47014 (14) | 0.0349 (7) | |
N6 | 0.50889 (6) | 0.2640 (4) | 0.49973 (15) | 0.0427 (8) | |
H6N | 0.4963 | 0.3127 | 0.4718 | 0.051* | 0.50 |
N7 | 0.52850 (6) | 0.1071 (3) | 0.58045 (15) | 0.0393 (7) | |
H7N | 0.5305 | 0.0422 | 0.6115 | 0.047* | 0.50 |
N8 | 0.62546 (6) | 0.2431 (3) | 0.56234 (13) | 0.0328 (6) | |
C1 | 0.68180 (7) | 0.5800 (4) | 0.42007 (15) | 0.0318 (7) | |
C2 | 0.67164 (7) | 0.5539 (4) | 0.34578 (15) | 0.0334 (8) | |
C3 | 0.68747 (8) | 0.4623 (4) | 0.31553 (18) | 0.0442 (9) | |
H3 | 0.7046 | 0.4257 | 0.3404 | 0.053* | |
C4 | 0.67855 (10) | 0.4222 (5) | 0.24807 (19) | 0.0520 (11) | |
H4 | 0.6904 | 0.3659 | 0.2282 | 0.062* | |
C5 | 0.65281 (9) | 0.4650 (4) | 0.21179 (17) | 0.0453 (10) | |
C6 | 0.63544 (8) | 0.5580 (4) | 0.24055 (17) | 0.0418 (9) | |
C7 | 0.60821 (10) | 0.6066 (6) | 0.2051 (2) | 0.0636 (14) | |
H7 | 0.6006 | 0.5699 | 0.1626 | 0.076* | |
C8 | 0.59313 (10) | 0.7050 (7) | 0.2321 (2) | 0.0763 (17) | |
H8 | 0.5750 | 0.7312 | 0.2087 | 0.092* | |
C9 | 0.60437 (9) | 0.7686 (6) | 0.2949 (2) | 0.0610 (13) | |
H9 | 0.5944 | 0.8414 | 0.3115 | 0.073* | |
C10 | 0.63004 (8) | 0.7224 (4) | 0.33118 (18) | 0.0446 (9) | |
H10 | 0.6375 | 0.7647 | 0.3726 | 0.053* | |
C11 | 0.64569 (8) | 0.6109 (4) | 0.30714 (16) | 0.0362 (8) | |
C12 | 0.64374 (11) | 0.4187 (5) | 0.13943 (18) | 0.0573 (12) | |
C13 | 0.63068 (8) | 0.2504 (4) | 0.36630 (17) | 0.0391 (8) | |
H13 | 0.6143 | 0.3071 | 0.3612 | 0.047* | |
C14 | 0.63352 (8) | 0.1611 (4) | 0.31385 (18) | 0.0443 (9) | |
H14 | 0.6195 | 0.1594 | 0.2745 | 0.053* | |
C15 | 0.65707 (7) | 0.0760 (4) | 0.32064 (16) | 0.0383 (8) | |
H15 | 0.6592 | 0.0140 | 0.2862 | 0.046* | |
C16 | 0.67804 (7) | 0.0824 (4) | 0.38000 (15) | 0.0309 (7) | |
C17 | 0.67358 (7) | 0.1766 (4) | 0.43056 (15) | 0.0277 (7) | |
C18 | 0.70380 (7) | −0.0002 (4) | 0.39249 (15) | 0.0302 (7) | |
C19 | 0.73844 (7) | −0.1426 (4) | 0.38480 (16) | 0.0319 (7) | |
C20 | 0.75594 (7) | −0.2469 (4) | 0.35910 (15) | 0.0310 (7) | |
C21 | 0.74440 (8) | −0.3234 (4) | 0.30051 (17) | 0.0375 (8) | |
H21 | 0.7256 | −0.3066 | 0.2787 | 0.045* | |
C22 | 0.76036 (7) | −0.4235 (4) | 0.27433 (16) | 0.0363 (8) | |
H22 | 0.7523 | −0.4730 | 0.2350 | 0.044* | |
C23 | 0.78818 (7) | −0.4505 (4) | 0.30626 (16) | 0.0326 (8) | |
C24 | 0.80001 (8) | −0.3755 (4) | 0.36495 (17) | 0.0394 (9) | |
H24 | 0.8187 | −0.3932 | 0.3868 | 0.047* | |
C25 | 0.78397 (8) | −0.2747 (4) | 0.39081 (17) | 0.0388 (8) | |
H25 | 0.7921 | −0.2249 | 0.4300 | 0.047* | |
C26 | 0.72353 (7) | 0.0112 (4) | 0.45189 (15) | 0.0305 (7) | |
C27 | 0.72016 (7) | 0.1082 (4) | 0.50390 (15) | 0.0303 (7) | |
C28 | 0.69495 (7) | 0.1906 (4) | 0.49268 (15) | 0.0289 (7) | |
C29 | 0.73988 (8) | 0.1291 (4) | 0.56409 (16) | 0.0368 (8) | |
H29 | 0.7567 | 0.0751 | 0.5734 | 0.044* | |
C30 | 0.73462 (8) | 0.2288 (4) | 0.60954 (17) | 0.0417 (9) | |
H30 | 0.7478 | 0.2448 | 0.6494 | 0.050* | |
C31 | 0.70901 (8) | 0.3062 (4) | 0.59476 (16) | 0.0370 (8) | |
H31 | 0.7054 | 0.3731 | 0.6260 | 0.044* | |
C32 | 0.58966 (8) | 0.5338 (4) | 0.42155 (17) | 0.0421 (9) | |
H32 | 0.6017 | 0.5940 | 0.4039 | 0.051* | |
C33 | 0.56062 (8) | 0.5453 (5) | 0.39549 (19) | 0.0472 (10) | |
H33 | 0.5536 | 0.6091 | 0.3603 | 0.057* | |
C34 | 0.54270 (8) | 0.4625 (4) | 0.42190 (18) | 0.0448 (9) | |
H34 | 0.5232 | 0.4703 | 0.4059 | 0.054* | |
C35 | 0.55415 (7) | 0.3645 (4) | 0.47394 (17) | 0.0352 (8) | |
C36 | 0.58368 (7) | 0.3551 (4) | 0.49587 (16) | 0.0308 (7) | |
C37 | 0.53799 (7) | 0.2739 (4) | 0.50782 (17) | 0.0375 (8) | |
C38 | 0.50402 (8) | 0.1628 (4) | 0.54421 (18) | 0.0390 (8) | |
C39 | 0.47567 (8) | 0.1240 (4) | 0.55059 (18) | 0.0398 (9) | |
C40 | 0.45204 (8) | 0.1852 (5) | 0.5075 (2) | 0.0466 (9) | |
H40 | 0.4546 | 0.2507 | 0.4746 | 0.056* | |
C41 | 0.42516 (8) | 0.1502 (4) | 0.51280 (19) | 0.0441 (9) | |
H41 | 0.4096 | 0.1918 | 0.4835 | 0.053* | |
C42 | 0.42095 (8) | 0.0535 (4) | 0.56145 (19) | 0.0418 (9) | |
C43 | 0.44413 (9) | −0.0074 (5) | 0.6052 (2) | 0.0502 (10) | |
H43 | 0.4415 | −0.0719 | 0.6383 | 0.060* | |
C44 | 0.47111 (9) | 0.0282 (5) | 0.59918 (19) | 0.0482 (10) | |
H44 | 0.4866 | −0.0133 | 0.6285 | 0.058* | |
C45 | 0.54997 (7) | 0.1768 (4) | 0.55707 (16) | 0.0360 (8) | |
C46 | 0.58004 (7) | 0.1575 (4) | 0.57679 (16) | 0.0317 (7) | |
C47 | 0.59665 (7) | 0.2488 (4) | 0.54633 (15) | 0.0301 (7) | |
C48 | 0.59376 (8) | 0.0503 (4) | 0.62186 (18) | 0.0423 (9) | |
H48 | 0.5833 | −0.0148 | 0.6417 | 0.051* | |
C49 | 0.62277 (8) | 0.0435 (4) | 0.63611 (18) | 0.0422 (9) | |
H49 | 0.6324 | −0.0275 | 0.6653 | 0.051* | |
C50 | 0.63774 (8) | 0.1443 (4) | 0.60637 (17) | 0.0391 (9) | |
H50 | 0.6575 | 0.1416 | 0.6182 | 0.047* | |
O7 | 0.57620 (11) | 0.3027 (6) | 0.1777 (3) | 0.0515 (14) | 0.50 |
H7O | 0.5886 | 0.3112 | 0.1568 | 0.062* | 0.50 |
O8 | 0.54490 (15) | 0.4380 (7) | 0.1031 (3) | 0.0662 (18) | 0.50 |
O9 | 0.47578 (12) | 0.3147 (7) | 0.3757 (3) | 0.0619 (16) | 0.50 |
O10 | 0.46652 (12) | 0.0992 (7) | 0.3243 (3) | 0.0651 (17) | 0.50 |
H10O | 0.4575 | 0.0738 | 0.3517 | 0.078* | 0.50 |
C51 | 0.55115 (11) | 0.3657 (5) | 0.1545 (2) | 0.0409 (17) | 0.50 |
C52 | 0.53036 (7) | 0.3410 (4) | 0.19789 (16) | 0.0385 (17) | 0.50 |
C53 | 0.52596 (9) | 0.1961 (4) | 0.2146 (2) | 0.049 (2) | 0.50 |
H53 | 0.5352 | 0.1200 | 0.1981 | 0.059* | 0.50 |
C54 | 0.50771 (9) | 0.1650 (3) | 0.2560 (2) | 0.047 (2) | 0.50 |
H54 | 0.5048 | 0.0681 | 0.2672 | 0.056* | 0.50 |
C55 | 0.49387 (8) | 0.2788 (4) | 0.28073 (17) | 0.0461 (19) | 0.50 |
C56 | 0.49827 (9) | 0.4237 (4) | 0.2640 (2) | 0.042 (3) | 0.50 |
C57 | 0.51652 (9) | 0.4548 (3) | 0.22257 (19) | 0.041 (2) | 0.50 |
C58 | 0.52092 (14) | 0.5997 (4) | 0.2058 (3) | 0.044 (2) | 0.50 |
H58 | 0.5331 | 0.6205 | 0.1781 | 0.053* | 0.50 |
C59 | 0.50708 (19) | 0.7134 (3) | 0.2305 (4) | 0.047 (3) | 0.50 |
H59 | 0.5100 | 0.8104 | 0.2193 | 0.057* | 0.50 |
C60 | 0.48883 (19) | 0.6823 (4) | 0.2719 (4) | 0.068 (4) | 0.50 |
H60 | 0.4796 | 0.7584 | 0.2884 | 0.082* | 0.50 |
C61 | 0.48443 (14) | 0.5374 (5) | 0.2887 (3) | 0.057 (3) | 0.50 |
H61 | 0.4722 | 0.5166 | 0.3164 | 0.068* | 0.50 |
C62 | 0.47719 (9) | 0.2234 (7) | 0.3285 (3) | 0.050 (2) | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.0325 (3) | 0.0381 (3) | 0.0258 (2) | 0.0015 (2) | 0.0110 (2) | −0.0006 (2) |
O1 | 0.0453 (15) | 0.0431 (14) | 0.0294 (12) | 0.0010 (12) | 0.0171 (11) | 0.0011 (11) |
O2 | 0.0342 (15) | 0.0710 (19) | 0.0338 (13) | 0.0000 (14) | 0.0048 (11) | −0.0056 (13) |
O3 | 0.0654 (19) | 0.0591 (17) | 0.0245 (12) | 0.0084 (15) | 0.0161 (12) | 0.0071 (12) |
O4 | 0.217 (5) | 0.161 (4) | 0.0387 (18) | −0.144 (4) | 0.040 (2) | −0.035 (2) |
O5 | 0.0398 (15) | 0.0600 (17) | 0.0289 (12) | 0.0147 (13) | 0.0063 (11) | −0.0057 (12) |
O6 | 0.0341 (15) | 0.080 (2) | 0.0612 (18) | −0.0089 (15) | 0.0143 (13) | 0.0063 (17) |
O1W | 0.063 (2) | 0.0632 (19) | 0.0460 (16) | 0.0125 (16) | 0.0062 (14) | −0.0068 (14) |
N1 | 0.0311 (15) | 0.0399 (16) | 0.0290 (14) | 0.0017 (13) | 0.0099 (12) | −0.0012 (13) |
N2 | 0.0337 (15) | 0.0388 (16) | 0.0262 (13) | 0.0026 (13) | 0.0087 (12) | −0.0015 (13) |
N3 | 0.0321 (15) | 0.0394 (16) | 0.0254 (13) | 0.0046 (13) | 0.0063 (11) | −0.0030 (13) |
N4 | 0.0352 (16) | 0.0368 (16) | 0.0260 (13) | 0.0003 (13) | 0.0092 (12) | −0.0023 (12) |
N5 | 0.0364 (16) | 0.0382 (16) | 0.0323 (14) | 0.0028 (13) | 0.0124 (13) | 0.0040 (13) |
N6 | 0.0330 (17) | 0.0523 (19) | 0.0438 (17) | −0.0035 (15) | 0.0109 (14) | 0.0065 (16) |
N7 | 0.0322 (16) | 0.0495 (18) | 0.0385 (16) | −0.0004 (14) | 0.0128 (13) | 0.0016 (14) |
N8 | 0.0298 (15) | 0.0368 (15) | 0.0325 (14) | 0.0026 (13) | 0.0084 (12) | 0.0012 (13) |
C1 | 0.0367 (19) | 0.0358 (18) | 0.0249 (15) | 0.0006 (16) | 0.0112 (14) | 0.0000 (15) |
C2 | 0.0381 (19) | 0.0400 (19) | 0.0236 (15) | −0.0060 (16) | 0.0100 (14) | 0.0004 (14) |
C3 | 0.045 (2) | 0.056 (2) | 0.0338 (18) | 0.0049 (19) | 0.0142 (17) | 0.0013 (18) |
C4 | 0.071 (3) | 0.056 (3) | 0.0351 (19) | 0.001 (2) | 0.025 (2) | −0.0081 (19) |
C5 | 0.066 (3) | 0.047 (2) | 0.0250 (17) | −0.019 (2) | 0.0147 (18) | −0.0020 (17) |
C6 | 0.046 (2) | 0.054 (2) | 0.0257 (16) | −0.0174 (19) | 0.0090 (16) | 0.0095 (16) |
C7 | 0.053 (3) | 0.105 (4) | 0.0291 (19) | −0.024 (3) | 0.0025 (19) | 0.016 (2) |
C8 | 0.040 (3) | 0.137 (5) | 0.052 (3) | 0.002 (3) | 0.010 (2) | 0.044 (3) |
C9 | 0.052 (3) | 0.085 (3) | 0.052 (2) | 0.020 (2) | 0.023 (2) | 0.029 (2) |
C10 | 0.046 (2) | 0.053 (2) | 0.0374 (19) | 0.0059 (19) | 0.0164 (17) | 0.0095 (18) |
C11 | 0.040 (2) | 0.045 (2) | 0.0260 (16) | −0.0073 (17) | 0.0123 (15) | 0.0060 (15) |
C12 | 0.091 (4) | 0.056 (3) | 0.0261 (18) | −0.027 (3) | 0.016 (2) | −0.0040 (18) |
C13 | 0.0334 (19) | 0.048 (2) | 0.0349 (18) | 0.0104 (17) | 0.0046 (15) | −0.0018 (17) |
C14 | 0.040 (2) | 0.057 (2) | 0.0319 (18) | 0.0058 (19) | 0.0005 (16) | −0.0063 (18) |
C15 | 0.037 (2) | 0.050 (2) | 0.0259 (16) | 0.0047 (17) | 0.0036 (14) | −0.0065 (16) |
C16 | 0.0302 (17) | 0.0365 (18) | 0.0267 (15) | 0.0009 (15) | 0.0079 (13) | 0.0009 (15) |
C17 | 0.0292 (17) | 0.0319 (17) | 0.0240 (15) | −0.0016 (14) | 0.0101 (13) | 0.0026 (14) |
C18 | 0.0328 (18) | 0.0345 (18) | 0.0242 (15) | −0.0004 (15) | 0.0081 (13) | −0.0003 (14) |
C19 | 0.0349 (19) | 0.0378 (18) | 0.0245 (15) | −0.0003 (16) | 0.0100 (14) | 0.0001 (14) |
C20 | 0.0345 (18) | 0.0346 (18) | 0.0254 (15) | −0.0001 (15) | 0.0102 (14) | 0.0000 (14) |
C21 | 0.0333 (19) | 0.046 (2) | 0.0328 (17) | 0.0057 (17) | 0.0059 (15) | −0.0018 (16) |
C22 | 0.038 (2) | 0.044 (2) | 0.0261 (16) | 0.0038 (17) | 0.0054 (14) | −0.0039 (15) |
C23 | 0.0329 (18) | 0.0381 (19) | 0.0286 (16) | 0.0056 (15) | 0.0105 (14) | 0.0018 (15) |
C24 | 0.0311 (19) | 0.052 (2) | 0.0328 (18) | 0.0045 (17) | 0.0033 (15) | −0.0039 (17) |
C25 | 0.037 (2) | 0.048 (2) | 0.0299 (17) | 0.0024 (17) | 0.0034 (15) | −0.0071 (16) |
C26 | 0.0332 (18) | 0.0330 (17) | 0.0268 (15) | 0.0008 (15) | 0.0100 (14) | 0.0010 (14) |
C27 | 0.0302 (17) | 0.0366 (18) | 0.0268 (15) | −0.0007 (15) | 0.0120 (13) | 0.0013 (14) |
C28 | 0.0318 (18) | 0.0303 (17) | 0.0262 (15) | −0.0040 (14) | 0.0101 (13) | 0.0001 (14) |
C29 | 0.0351 (19) | 0.046 (2) | 0.0290 (16) | 0.0058 (16) | 0.0063 (15) | −0.0019 (16) |
C30 | 0.040 (2) | 0.054 (2) | 0.0295 (17) | −0.0006 (19) | 0.0056 (16) | −0.0060 (17) |
C31 | 0.039 (2) | 0.043 (2) | 0.0289 (17) | −0.0010 (17) | 0.0090 (15) | −0.0066 (16) |
C32 | 0.042 (2) | 0.049 (2) | 0.0361 (18) | −0.0013 (18) | 0.0110 (16) | 0.0100 (18) |
C33 | 0.044 (2) | 0.054 (2) | 0.041 (2) | 0.0009 (19) | 0.0049 (18) | 0.0148 (19) |
C34 | 0.037 (2) | 0.055 (2) | 0.039 (2) | 0.0008 (19) | 0.0008 (16) | 0.0106 (19) |
C35 | 0.0342 (19) | 0.042 (2) | 0.0307 (17) | −0.0010 (16) | 0.0091 (15) | 0.0025 (16) |
C36 | 0.0323 (18) | 0.0346 (18) | 0.0274 (16) | −0.0006 (15) | 0.0105 (14) | −0.0029 (14) |
C37 | 0.0311 (19) | 0.050 (2) | 0.0309 (17) | −0.0002 (17) | 0.0063 (15) | 0.0032 (17) |
C38 | 0.036 (2) | 0.045 (2) | 0.0395 (19) | −0.0020 (17) | 0.0160 (16) | 0.0007 (17) |
C39 | 0.037 (2) | 0.046 (2) | 0.0386 (19) | −0.0034 (17) | 0.0139 (16) | −0.0045 (17) |
C40 | 0.043 (2) | 0.052 (2) | 0.048 (2) | −0.0024 (19) | 0.0168 (18) | 0.0041 (19) |
C41 | 0.039 (2) | 0.051 (2) | 0.043 (2) | −0.0001 (18) | 0.0112 (17) | −0.0025 (19) |
C42 | 0.035 (2) | 0.050 (2) | 0.043 (2) | −0.0077 (17) | 0.0151 (16) | −0.0104 (18) |
C43 | 0.046 (2) | 0.062 (3) | 0.046 (2) | −0.007 (2) | 0.0171 (19) | 0.006 (2) |
C44 | 0.041 (2) | 0.060 (3) | 0.043 (2) | 0.001 (2) | 0.0106 (17) | 0.010 (2) |
C45 | 0.035 (2) | 0.044 (2) | 0.0308 (17) | −0.0026 (17) | 0.0115 (15) | 0.0003 (16) |
C46 | 0.0331 (19) | 0.0352 (18) | 0.0270 (16) | 0.0029 (15) | 0.0071 (14) | −0.0005 (15) |
C47 | 0.0318 (18) | 0.0328 (17) | 0.0262 (15) | −0.0006 (15) | 0.0076 (14) | −0.0032 (14) |
C48 | 0.044 (2) | 0.045 (2) | 0.0374 (19) | 0.0030 (18) | 0.0094 (17) | 0.0073 (17) |
C49 | 0.045 (2) | 0.043 (2) | 0.0391 (19) | 0.0104 (18) | 0.0096 (17) | 0.0120 (17) |
C50 | 0.037 (2) | 0.046 (2) | 0.0351 (18) | 0.0063 (17) | 0.0103 (16) | 0.0060 (17) |
O7 | 0.048 (3) | 0.060 (3) | 0.053 (3) | −0.014 (3) | 0.025 (3) | 0.002 (3) |
O8 | 0.092 (5) | 0.072 (4) | 0.044 (3) | 0.014 (3) | 0.033 (3) | 0.016 (3) |
O9 | 0.052 (3) | 0.088 (4) | 0.050 (3) | 0.004 (3) | 0.021 (3) | 0.023 (3) |
O10 | 0.057 (4) | 0.074 (4) | 0.068 (4) | −0.012 (3) | 0.023 (3) | 0.030 (3) |
C51 | 0.044 (4) | 0.043 (4) | 0.039 (4) | −0.007 (3) | 0.016 (3) | −0.009 (3) |
C52 | 0.039 (4) | 0.041 (4) | 0.036 (3) | −0.005 (3) | 0.010 (3) | −0.001 (3) |
C53 | 0.072 (5) | 0.042 (4) | 0.033 (4) | −0.005 (4) | 0.013 (4) | 0.000 (4) |
C54 | 0.064 (7) | 0.039 (3) | 0.033 (4) | −0.013 (3) | 0.004 (4) | 0.002 (4) |
C55 | 0.039 (4) | 0.054 (4) | 0.044 (4) | 0.002 (4) | 0.006 (3) | 0.022 (4) |
C56 | 0.046 (4) | 0.045 (4) | 0.029 (6) | 0.003 (5) | −0.008 (4) | 0.010 (3) |
C57 | 0.045 (5) | 0.041 (5) | 0.031 (4) | −0.002 (4) | −0.002 (4) | 0.005 (4) |
C58 | 0.041 (5) | 0.047 (5) | 0.045 (4) | −0.004 (4) | 0.008 (4) | −0.015 (4) |
C59 | 0.065 (6) | 0.027 (4) | 0.050 (6) | −0.002 (4) | 0.014 (5) | −0.001 (4) |
C60 | 0.062 (7) | 0.075 (6) | 0.072 (8) | 0.011 (6) | 0.023 (6) | −0.009 (6) |
C61 | 0.036 (5) | 0.080 (7) | 0.057 (6) | 0.003 (5) | 0.018 (4) | 0.012 (5) |
C62 | 0.036 (4) | 0.061 (5) | 0.055 (5) | −0.003 (4) | 0.011 (4) | 0.014 (4) |
Mn1—O1 | 2.146 (2) | C21—H21 | 0.9300 |
Mn1—O3i | 2.108 (2) | C22—C23 | 1.379 (5) |
Mn1—N1 | 2.282 (3) | C22—H22 | 0.9300 |
Mn1—N4 | 2.245 (3) | C23—C24 | 1.392 (5) |
Mn1—N5 | 2.265 (3) | C24—C25 | 1.384 (5) |
Mn1—N8 | 2.307 (3) | C24—H24 | 0.9300 |
O1—C1 | 1.282 (4) | C25—H25 | 0.9300 |
O2—C1 | 1.232 (4) | C26—C27 | 1.425 (4) |
O3—C12 | 1.239 (5) | C27—C29 | 1.394 (4) |
O3—Mn1ii | 2.108 (2) | C27—C28 | 1.405 (5) |
O4—C12 | 1.232 (5) | C29—C30 | 1.368 (5) |
O5—C23 | 1.354 (4) | C29—H29 | 0.9300 |
O5—H5O | 0.8200 | C30—C31 | 1.397 (5) |
O6—C42 | 1.352 (4) | C30—H30 | 0.9300 |
O6—H6O | 0.8200 | C31—H31 | 0.9300 |
O1W—H1W1 | 0.8201 | C32—C33 | 1.389 (5) |
O1W—H1W2 | 0.8200 | C32—H32 | 0.9300 |
N1—C13 | 1.323 (4) | C33—C34 | 1.352 (5) |
N1—C17 | 1.353 (4) | C33—H33 | 0.9300 |
N2—C19 | 1.329 (4) | C34—C35 | 1.407 (5) |
N2—C18 | 1.379 (4) | C34—H34 | 0.9300 |
N3—C19 | 1.361 (4) | C35—C36 | 1.400 (5) |
N3—C26 | 1.376 (4) | C35—C37 | 1.423 (5) |
N3—H3N | 0.8600 | C36—C47 | 1.453 (5) |
N4—C31 | 1.323 (4) | C37—C45 | 1.369 (5) |
N4—C28 | 1.364 (4) | C38—C39 | 1.452 (5) |
N5—C32 | 1.327 (4) | C39—C44 | 1.382 (5) |
N5—C36 | 1.352 (4) | C39—C40 | 1.394 (5) |
N6—C38 | 1.356 (5) | C40—C41 | 1.368 (5) |
N6—C37 | 1.383 (4) | C40—H40 | 0.9300 |
N6—H6N | 0.8600 | C41—C42 | 1.383 (5) |
N7—C38 | 1.347 (5) | C41—H41 | 0.9300 |
N7—C45 | 1.393 (4) | C42—C43 | 1.384 (5) |
N7—H7N | 0.8600 | C43—C44 | 1.378 (5) |
N8—C50 | 1.318 (4) | C43—H43 | 0.9300 |
N8—C47 | 1.359 (4) | C44—H44 | 0.9300 |
C1—C2 | 1.515 (4) | C45—C46 | 1.430 (5) |
C2—C3 | 1.374 (5) | C46—C47 | 1.400 (5) |
C2—C11 | 1.422 (5) | C46—C48 | 1.403 (5) |
C3—C4 | 1.406 (5) | C48—C49 | 1.369 (5) |
C3—H3 | 0.9300 | C48—H48 | 0.9300 |
C4—C5 | 1.355 (6) | C49—C50 | 1.394 (5) |
C4—H4 | 0.9300 | C49—H49 | 0.9300 |
C5—C6 | 1.414 (6) | C50—H50 | 0.9300 |
C5—C12 | 1.514 (5) | O7—C51 | 1.327 (6) |
C6—C7 | 1.423 (6) | O7—H7O | 0.8201 |
C6—C11 | 1.431 (5) | O8—C51 | 1.223 (6) |
C7—C8 | 1.351 (7) | O9—C62 | 1.291 (7) |
C7—H7 | 0.9300 | O10—C62 | 1.236 (7) |
C8—C9 | 1.409 (7) | O10—H10O | 0.8198 |
C8—H8 | 0.9300 | C51—C52 | 1.507 (5) |
C9—C10 | 1.362 (5) | C52—C53 | 1.3900 |
C9—H9 | 0.9300 | C52—C57 | 1.3900 |
C10—C11 | 1.420 (5) | C53—C54 | 1.3900 |
C10—H10 | 0.9300 | C53—H53 | 0.9300 |
C13—C14 | 1.383 (5) | C54—C55 | 1.3900 |
C13—H13 | 0.9300 | C54—H54 | 0.9300 |
C14—C15 | 1.358 (5) | C55—C56 | 1.3900 |
C14—H14 | 0.9300 | C55—C62 | 1.496 (5) |
C15—C16 | 1.401 (4) | C56—C57 | 1.3900 |
C15—H15 | 0.9300 | C56—C61 | 1.3900 |
C16—C17 | 1.402 (4) | C57—C58 | 1.3900 |
C16—C18 | 1.427 (5) | C58—C59 | 1.3900 |
C17—C28 | 1.455 (4) | C58—H58 | 0.9300 |
C18—C26 | 1.373 (4) | C59—C60 | 1.3900 |
C19—C20 | 1.449 (5) | C59—H59 | 0.9300 |
C20—C25 | 1.388 (5) | C60—C61 | 1.3900 |
C20—C21 | 1.394 (5) | C60—H60 | 0.9300 |
C21—C22 | 1.381 (5) | C61—H61 | 0.9300 |
O1—Mn1—O3i | 95.0 (1) | C24—C25—H25 | 119.5 |
O1—Mn1—N1 | 87.1 (1) | C20—C25—H25 | 119.5 |
O1—Mn1—N4 | 97.6 (1) | C18—C26—N3 | 106.0 (3) |
O1—Mn1—N5 | 97.9 (1) | C18—C26—C27 | 122.7 (3) |
O1—Mn1—N8 | 169.9 (1) | N3—C26—C27 | 131.2 (3) |
O3i—Mn1—N1 | 165.2 (1) | C29—C27—C28 | 117.8 (3) |
O3i—Mn1—N4 | 91.8 (1) | C29—C27—C26 | 125.4 (3) |
O3i—Mn1—N5 | 104.8 (1) | C28—C27—C26 | 116.8 (3) |
O3i—Mn1—N8 | 87.1 (1) | N4—C28—C27 | 121.8 (3) |
N1—Mn1—N4 | 73.4 (1) | N4—C28—C17 | 117.2 (3) |
N1—Mn1—N5 | 89.5 (1) | C27—C28—C17 | 120.9 (3) |
N1—Mn1—N8 | 93.4 (1) | C30—C29—C27 | 120.1 (3) |
N4—Mn1—N5 | 156.2 (1) | C30—C29—H29 | 119.9 |
N4—Mn1—N8 | 92.2 (1) | C27—C29—H29 | 119.9 |
N5—Mn1—N8 | 72.0 (1) | C29—C30—C31 | 118.6 (3) |
C1—O1—Mn1 | 129.1 (2) | C29—C30—H30 | 120.7 |
C12—O3—Mn1ii | 136.2 (3) | C31—C30—H30 | 120.7 |
C23—O5—H5O | 109.5 | N4—C31—C30 | 123.1 (3) |
C42—O6—H6O | 109.5 | N4—C31—H31 | 118.5 |
H1W1—O1W—H1W2 | 108.2 | C30—C31—H31 | 118.5 |
C13—N1—C17 | 117.9 (3) | N5—C32—C33 | 123.7 (4) |
C13—N1—Mn1 | 126.6 (2) | N5—C32—H32 | 118.1 |
C17—N1—Mn1 | 115.4 (2) | C33—C32—H32 | 118.1 |
C19—N2—C18 | 105.3 (3) | C34—C33—C32 | 119.2 (4) |
C19—N3—C26 | 107.0 (3) | C34—C33—H33 | 120.4 |
C19—N3—H3N | 126.5 | C32—C33—H33 | 120.4 |
C26—N3—H3N | 126.5 | C33—C34—C35 | 118.8 (4) |
C31—N4—C28 | 118.5 (3) | C33—C34—H34 | 120.6 |
C31—N4—Mn1 | 125.0 (2) | C35—C34—H34 | 120.6 |
C28—N4—Mn1 | 116.4 (2) | C36—C35—C34 | 118.7 (3) |
C32—N5—C36 | 117.9 (3) | C36—C35—C37 | 116.2 (3) |
C32—N5—Mn1 | 124.5 (2) | C34—C35—C37 | 125.1 (3) |
C36—N5—Mn1 | 117.6 (2) | N5—C36—C35 | 121.7 (3) |
C38—N6—C37 | 107.0 (3) | N5—C36—C47 | 117.4 (3) |
C38—N6—H6N | 126.5 | C35—C36—C47 | 120.9 (3) |
C37—N6—H6N | 126.5 | C45—C37—N6 | 107.1 (3) |
C38—N7—C45 | 105.6 (3) | C45—C37—C35 | 123.3 (3) |
C38—N7—H7N | 127.2 | N6—C37—C35 | 129.6 (3) |
C45—N7—H7N | 127.2 | N7—C38—N6 | 111.3 (3) |
C50—N8—C47 | 118.0 (3) | N7—C38—C39 | 126.1 (3) |
C50—N8—Mn1 | 125.8 (2) | N6—C38—C39 | 122.7 (3) |
C47—N8—Mn1 | 116.2 (2) | C44—C39—C40 | 118.0 (4) |
O2—C1—O1 | 124.5 (3) | C44—C39—C38 | 122.0 (3) |
O2—C1—C2 | 118.9 (3) | C40—C39—C38 | 120.0 (3) |
O1—C1—C2 | 116.6 (3) | C41—C40—C39 | 120.9 (4) |
C3—C2—C11 | 118.7 (3) | C41—C40—H40 | 119.6 |
C3—C2—C1 | 117.8 (3) | C39—C40—H40 | 119.6 |
C11—C2—C1 | 123.4 (3) | C40—C41—C42 | 120.4 (4) |
C2—C3—C4 | 121.9 (4) | C40—C41—H41 | 119.8 |
C2—C3—H3 | 119.1 | C42—C41—H41 | 119.8 |
C4—C3—H3 | 119.1 | O6—C42—C41 | 122.5 (4) |
C5—C4—C3 | 120.4 (4) | O6—C42—C43 | 117.8 (4) |
C5—C4—H4 | 119.8 | C41—C42—C43 | 119.7 (4) |
C3—C4—H4 | 119.8 | C44—C43—C42 | 119.4 (4) |
C4—C5—C6 | 120.0 (3) | C44—C43—H43 | 120.3 |
C4—C5—C12 | 119.1 (4) | C42—C43—H43 | 120.3 |
C6—C5—C12 | 120.8 (4) | C43—C44—C39 | 121.6 (4) |
C5—C6—C7 | 122.7 (4) | C43—C44—H44 | 119.2 |
C5—C6—C11 | 119.5 (4) | C39—C44—H44 | 119.2 |
C7—C6—C11 | 117.7 (4) | C37—C45—N7 | 109.1 (3) |
C8—C7—C6 | 121.3 (4) | C37—C45—C46 | 121.4 (3) |
C8—C7—H7 | 119.4 | N7—C45—C46 | 129.6 (3) |
C6—C7—H7 | 119.4 | C47—C46—C48 | 118.3 (3) |
C7—C8—C9 | 121.2 (4) | C47—C46—C45 | 116.8 (3) |
C7—C8—H8 | 119.4 | C48—C46—C45 | 124.8 (3) |
C9—C8—H8 | 119.4 | N8—C47—C46 | 122.1 (3) |
C10—C9—C8 | 119.3 (5) | N8—C47—C36 | 116.8 (3) |
C10—C9—H9 | 120.3 | C46—C47—C36 | 121.1 (3) |
C8—C9—H9 | 120.3 | C49—C48—C46 | 118.7 (4) |
C9—C10—C11 | 121.4 (4) | C49—C48—H48 | 120.6 |
C9—C10—H10 | 119.3 | C46—C48—H48 | 120.6 |
C11—C10—H10 | 119.3 | C48—C49—C50 | 119.1 (3) |
C10—C11—C2 | 122.5 (3) | C48—C49—H49 | 120.4 |
C10—C11—C6 | 118.6 (3) | C50—C49—H49 | 120.4 |
C2—C11—C6 | 118.9 (3) | N8—C50—C49 | 123.5 (4) |
O4—C12—O3 | 123.9 (4) | N8—C50—H50 | 118.2 |
O4—C12—C5 | 119.8 (4) | C49—C50—H50 | 118.2 |
O3—C12—C5 | 116.3 (4) | C51—O7—H7O | 119.4 |
N1—C13—C14 | 123.8 (3) | C62—O10—H10O | 119.1 |
N1—C13—H13 | 118.1 | O8—C51—O7 | 124.6 (6) |
C14—C13—H13 | 118.1 | O8—C51—C52 | 121.8 (5) |
C15—C14—C13 | 119.0 (3) | O7—C51—C52 | 113.7 (4) |
C15—C14—H14 | 120.5 | C53—C52—C57 | 120.0 |
C13—C14—H14 | 120.5 | C53—C52—C51 | 116.7 (3) |
C14—C15—C16 | 119.3 (3) | C57—C52—C51 | 123.3 (3) |
C14—C15—H15 | 120.3 | C52—C53—C54 | 120.0 |
C16—C15—H15 | 120.3 | C52—C53—H53 | 120.0 |
C17—C16—C15 | 118.0 (3) | C54—C53—H53 | 120.0 |
C17—C16—C18 | 117.6 (3) | C55—C54—C53 | 120.0 |
C15—C16—C18 | 124.4 (3) | C55—C54—H54 | 120.0 |
N1—C17—C16 | 122.0 (3) | C53—C54—H54 | 120.0 |
N1—C17—C28 | 117.6 (3) | C54—C55—C56 | 120.0 |
C16—C17—C28 | 120.5 (3) | C54—C55—C62 | 111.6 (3) |
C26—C18—N2 | 110.0 (3) | C56—C55—C62 | 128.2 (3) |
C26—C18—C16 | 121.5 (3) | C55—C56—C57 | 120.0 |
N2—C18—C16 | 128.5 (3) | C55—C56—C61 | 120.0 |
N2—C19—N3 | 111.6 (3) | C57—C56—C61 | 120.0 |
N2—C19—C20 | 123.7 (3) | C58—C57—C56 | 120.0 |
N3—C19—C20 | 124.7 (3) | C58—C57—C52 | 120.0 |
C25—C20—C21 | 118.2 (3) | C56—C57—C52 | 120.0 |
C25—C20—C19 | 122.5 (3) | C57—C58—C59 | 120.0 |
C21—C20—C19 | 119.3 (3) | C57—C58—H58 | 120.0 |
C22—C21—C20 | 121.2 (3) | C59—C58—H58 | 120.0 |
C22—C21—H21 | 119.4 | C58—C59—C60 | 120.0 |
C20—C21—H21 | 119.4 | C58—C59—H59 | 120.0 |
C23—C22—C21 | 120.2 (3) | C60—C59—H59 | 120.0 |
C23—C22—H22 | 119.9 | C61—C60—C59 | 120.0 |
C21—C22—H22 | 119.9 | C61—C60—H60 | 120.0 |
O5—C23—C22 | 123.2 (3) | C59—C60—H60 | 120.0 |
O5—C23—C24 | 117.4 (3) | C60—C61—C56 | 120.0 |
C22—C23—C24 | 119.4 (3) | C60—C61—H61 | 120.0 |
C25—C24—C23 | 120.2 (3) | C56—C61—H61 | 120.0 |
C25—C24—H24 | 119.9 | O10—C62—O9 | 123.2 (6) |
C23—C24—H24 | 119.9 | O10—C62—C55 | 122.7 (6) |
C24—C25—C20 | 120.9 (3) | O9—C62—C55 | 114.1 (5) |
O3i—Mn1—O1—C1 | 122.4 (3) | C19—N3—C26—C18 | 0.4 (4) |
N4—Mn1—O1—C1 | 30.0 (3) | C19—N3—C26—C27 | −176.7 (3) |
N5—Mn1—O1—C1 | −131.9 (3) | C18—C26—C27—C29 | −177.3 (3) |
N1—Mn1—O1—C1 | −42.8 (3) | N3—C26—C27—C29 | −0.6 (6) |
N8—Mn1—O1—C1 | −136.0 (5) | C18—C26—C27—C28 | 1.8 (5) |
O3i—Mn1—N1—C13 | −177.0 (4) | N3—C26—C27—C28 | 178.4 (3) |
O1—Mn1—N1—C13 | −78.7 (3) | C31—N4—C28—C27 | 0.1 (5) |
N4—Mn1—N1—C13 | −177.5 (3) | Mn1—N4—C28—C27 | 178.8 (2) |
N5—Mn1—N1—C13 | 19.3 (3) | C31—N4—C28—C17 | −178.5 (3) |
N8—Mn1—N1—C13 | 91.2 (3) | Mn1—N4—C28—C17 | 0.2 (4) |
O3i—Mn1—N1—C17 | −0.7 (6) | C29—C27—C28—N4 | 0.3 (5) |
O1—Mn1—N1—C17 | 97.6 (2) | C26—C27—C28—N4 | −178.8 (3) |
N4—Mn1—N1—C17 | −1.2 (2) | C29—C27—C28—C17 | 178.9 (3) |
N5—Mn1—N1—C17 | −164.4 (2) | C26—C27—C28—C17 | −0.2 (4) |
N8—Mn1—N1—C17 | −92.5 (2) | N1—C17—C28—N4 | −1.3 (4) |
O3i—Mn1—N4—C31 | −0.8 (3) | C16—C17—C28—N4 | 177.4 (3) |
O1—Mn1—N4—C31 | 94.4 (3) | N1—C17—C28—C27 | −179.9 (3) |
N5—Mn1—N4—C31 | −135.3 (3) | C16—C17—C28—C27 | −1.3 (5) |
N1—Mn1—N4—C31 | 179.1 (3) | C28—C27—C29—C30 | −1.0 (5) |
N8—Mn1—N4—C31 | −88.0 (3) | C26—C27—C29—C30 | 178.0 (3) |
O3i—Mn1—N4—C28 | −179.4 (2) | C27—C29—C30—C31 | 1.2 (6) |
O1—Mn1—N4—C28 | −84.1 (2) | C28—N4—C31—C30 | 0.1 (5) |
N5—Mn1—N4—C28 | 46.1 (4) | Mn1—N4—C31—C30 | −178.5 (3) |
N1—Mn1—N4—C28 | 0.5 (2) | C29—C30—C31—N4 | −0.7 (6) |
N8—Mn1—N4—C28 | 93.4 (2) | C36—N5—C32—C33 | −0.5 (6) |
O3i—Mn1—N5—C32 | 102.6 (3) | Mn1—N5—C32—C33 | 177.0 (3) |
O1—Mn1—N5—C32 | 5.3 (3) | N5—C32—C33—C34 | 2.3 (6) |
N4—Mn1—N5—C32 | −124.9 (3) | C32—C33—C34—C35 | −1.6 (6) |
N1—Mn1—N5—C32 | −81.7 (3) | C33—C34—C35—C36 | −0.8 (6) |
N8—Mn1—N5—C32 | −175.4 (3) | C33—C34—C35—C37 | 178.1 (4) |
O3i—Mn1—N5—C36 | −79.9 (3) | C32—N5—C36—C35 | −2.0 (5) |
O1—Mn1—N5—C36 | −177.2 (2) | Mn1—N5—C36—C35 | −179.7 (3) |
N4—Mn1—N5—C36 | 52.6 (4) | C32—N5—C36—C47 | 176.5 (3) |
N1—Mn1—N5—C36 | 95.8 (2) | Mn1—N5—C36—C47 | −1.1 (4) |
N8—Mn1—N5—C36 | 2.0 (2) | C34—C35—C36—N5 | 2.7 (5) |
O3i—Mn1—N8—C50 | −75.1 (3) | C37—C35—C36—N5 | −176.3 (3) |
O1—Mn1—N8—C50 | −177.4 (5) | C34—C35—C36—C47 | −175.9 (3) |
N4—Mn1—N8—C50 | 16.5 (3) | C37—C35—C36—C47 | 5.2 (5) |
N5—Mn1—N8—C50 | 178.3 (3) | C38—N6—C37—C45 | 0.4 (4) |
N1—Mn1—N8—C50 | 90.0 (3) | C38—N6—C37—C35 | −179.4 (4) |
O3i—Mn1—N8—C47 | 103.7 (2) | C36—C35—C37—C45 | −3.0 (5) |
O1—Mn1—N8—C47 | 1.5 (7) | C34—C35—C37—C45 | 178.1 (4) |
N4—Mn1—N8—C47 | −164.6 (2) | C36—C35—C37—N6 | 176.8 (4) |
N5—Mn1—N8—C47 | −2.8 (2) | C34—C35—C37—N6 | −2.1 (7) |
N1—Mn1—N8—C47 | −91.1 (2) | C45—N7—C38—N6 | −0.3 (4) |
Mn1—O1—C1—O2 | −80.7 (4) | C45—N7—C38—C39 | −179.8 (4) |
Mn1—O1—C1—C2 | 96.7 (3) | C37—N6—C38—N7 | −0.1 (4) |
O2—C1—C2—C3 | 37.7 (5) | C37—N6—C38—C39 | 179.4 (3) |
O1—C1—C2—C3 | −139.9 (4) | N7—C38—C39—C44 | 3.9 (6) |
O2—C1—C2—C11 | −146.9 (4) | N6—C38—C39—C44 | −175.5 (4) |
O1—C1—C2—C11 | 35.6 (5) | N7—C38—C39—C40 | −176.9 (4) |
C11—C2—C3—C4 | −0.8 (6) | N6—C38—C39—C40 | 3.7 (6) |
C1—C2—C3—C4 | 174.8 (3) | C44—C39—C40—C41 | −0.6 (6) |
C2—C3—C4—C5 | −4.7 (6) | C38—C39—C40—C41 | −179.8 (4) |
C3—C4—C5—C6 | 3.8 (6) | C39—C40—C41—C42 | 0.2 (6) |
C3—C4—C5—C12 | −179.4 (4) | C40—C41—C42—O6 | −178.9 (4) |
C4—C5—C6—C7 | −179.9 (4) | C40—C41—C42—C43 | 0.4 (6) |
C12—C5—C6—C7 | 3.4 (6) | O6—C42—C43—C44 | 178.7 (4) |
C4—C5—C6—C11 | 2.4 (6) | C41—C42—C43—C44 | −0.6 (6) |
C12—C5—C6—C11 | −174.3 (3) | C42—C43—C44—C39 | 0.2 (7) |
C5—C6—C7—C8 | −174.5 (4) | C40—C39—C44—C43 | 0.3 (6) |
C11—C6—C7—C8 | 3.3 (6) | C38—C39—C44—C43 | 179.6 (4) |
C6—C7—C8—C9 | 3.1 (7) | N6—C37—C45—N7 | −0.7 (4) |
C7—C8—C9—C10 | −4.7 (7) | C35—C37—C45—N7 | 179.2 (3) |
C8—C9—C10—C11 | −0.3 (6) | N6—C37—C45—C46 | 178.6 (3) |
C9—C10—C11—C2 | −175.8 (4) | C35—C37—C45—C46 | −1.6 (6) |
C9—C10—C11—C6 | 6.6 (5) | C38—N7—C45—C37 | 0.6 (4) |
C3—C2—C11—C10 | −170.6 (3) | C38—N7—C45—C46 | −178.5 (4) |
C1—C2—C11—C10 | 14.0 (5) | C37—C45—C46—C47 | 3.9 (5) |
C3—C2—C11—C6 | 6.9 (5) | N7—C45—C46—C47 | −177.1 (3) |
C1—C2—C11—C6 | −168.4 (3) | C37—C45—C46—C48 | −173.3 (3) |
C5—C6—C11—C10 | 169.9 (3) | N7—C45—C46—C48 | 5.8 (6) |
C7—C6—C11—C10 | −8.0 (5) | C50—N8—C47—C46 | 2.4 (5) |
C5—C6—C11—C2 | −7.8 (5) | Mn1—N8—C47—C46 | −176.6 (2) |
C7—C6—C11—C2 | 174.4 (3) | C50—N8—C47—C36 | −177.8 (3) |
Mn1ii—O3—C12—O4 | 53.9 (8) | Mn1—N8—C47—C36 | 3.3 (4) |
Mn1ii—O3—C12—C5 | −126.4 (4) | C48—C46—C47—N8 | −4.4 (5) |
C4—C5—C12—O4 | 113.9 (6) | C45—C46—C47—N8 | 178.2 (3) |
C6—C5—C12—O4 | −69.4 (7) | C48—C46—C47—C36 | 175.8 (3) |
C4—C5—C12—O3 | −65.9 (6) | C45—C46—C47—C36 | −1.6 (5) |
C6—C5—C12—O3 | 110.9 (5) | N5—C36—C47—N8 | −1.5 (4) |
C17—N1—C13—C14 | −0.2 (6) | C35—C36—C47—N8 | 177.1 (3) |
Mn1—N1—C13—C14 | 176.1 (3) | N5—C36—C47—C46 | 178.4 (3) |
N1—C13—C14—C15 | 0.8 (6) | C35—C36—C47—C46 | −3.0 (5) |
C13—C14—C15—C16 | −1.0 (6) | C47—C46—C48—C49 | 2.6 (5) |
C14—C15—C16—C17 | 0.6 (5) | C45—C46—C48—C49 | 179.7 (4) |
C14—C15—C16—C18 | −179.1 (3) | C46—C48—C49—C50 | 1.0 (6) |
C13—N1—C17—C16 | −0.3 (5) | C47—N8—C50—C49 | 1.5 (5) |
Mn1—N1—C17—C16 | −176.9 (2) | Mn1—N8—C50—C49 | −179.7 (3) |
C13—N1—C17—C28 | 178.3 (3) | C48—C49—C50—N8 | −3.2 (6) |
Mn1—N1—C17—C28 | 1.7 (4) | O8—C51—C52—C53 | 127.7 (3) |
C15—C16—C17—N1 | 0.1 (5) | O7—C51—C52—C53 | −52.4 (3) |
C18—C16—C17—N1 | 179.8 (3) | O8—C51—C52—C57 | −54.2 (3) |
C15—C16—C17—C28 | −178.5 (3) | O7—C51—C52—C57 | 125.7 (3) |
C18—C16—C17—C28 | 1.2 (5) | C57—C52—C53—C54 | 0.0 |
C19—N2—C18—C26 | 1.5 (4) | C51—C52—C53—C54 | 178.2 (2) |
C19—N2—C18—C16 | 179.4 (3) | C52—C53—C54—C55 | 0.0 |
C17—C16—C18—C26 | 0.3 (5) | C53—C54—C55—C56 | 0.0 |
C15—C16—C18—C26 | 180.0 (3) | C53—C54—C55—C62 | −175.3 (2) |
C17—C16—C18—N2 | −177.4 (3) | C54—C55—C56—C57 | 0.0 |
C15—C16—C18—N2 | 2.3 (6) | C62—C55—C56—C57 | 174.4 (2) |
C18—N2—C19—N3 | −1.2 (4) | C54—C55—C56—C61 | 180.0 |
C18—N2—C19—C20 | 179.2 (3) | C62—C55—C56—C61 | −5.6 (2) |
C26—N3—C19—N2 | 0.6 (4) | C55—C56—C57—C58 | 180.0 |
C26—N3—C19—C20 | −179.9 (3) | C61—C56—C57—C58 | 0.0 |
N2—C19—C20—C25 | 168.0 (3) | C55—C56—C57—C52 | 0.0 |
N3—C19—C20—C25 | −11.5 (5) | C61—C56—C57—C52 | 180.0 |
N2—C19—C20—C21 | −12.3 (5) | C53—C52—C57—C58 | 180.0 |
N3—C19—C20—C21 | 168.2 (3) | C51—C52—C57—C58 | 2.0 (2) |
C25—C20—C21—C22 | −0.4 (5) | C53—C52—C57—C56 | 0.0 |
C19—C20—C21—C22 | 179.9 (3) | C51—C52—C57—C56 | −178.0 (2) |
C20—C21—C22—C23 | 0.4 (6) | C56—C57—C58—C59 | 0.0 |
C21—C22—C23—O5 | 178.4 (3) | C52—C57—C58—C59 | 180.0 |
C21—C22—C23—C24 | −0.2 (5) | C57—C58—C59—C60 | 0.0 |
O5—C23—C24—C25 | −178.8 (3) | C58—C59—C60—C61 | 0.0 |
C22—C23—C24—C25 | −0.2 (6) | C59—C60—C61—C56 | 0.0 |
C23—C24—C25—C20 | 0.2 (6) | C55—C56—C61—C60 | 180.0 |
C21—C20—C25—C24 | 0.0 (5) | C57—C56—C61—C60 | 0.0 |
C19—C20—C25—C24 | 179.8 (3) | C54—C55—C62—O10 | −30.3 (3) |
N2—C18—C26—N3 | −1.1 (4) | C56—C55—C62—O10 | 154.9 (3) |
C16—C18—C26—N3 | −179.2 (3) | C54—C55—C62—O9 | 147.5 (3) |
N2—C18—C26—C27 | 176.2 (3) | C56—C55—C62—O9 | −27.3 (3) |
C16—C18—C26—C27 | −1.8 (5) |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, −y+1, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5O···N2iii | 0.82 | 1.93 | 2.737 (4) | 168 |
O6—H6O···O1Wiv | 0.82 | 1.85 | 2.656 (4) | 168 |
N3—H3N···O2v | 0.86 | 1.97 | 2.813 (4) | 166 |
N6—H6N···O9 | 0.86 | 2.00 | 2.728 (6) | 142 |
N7—H7N···O10vi | 0.86 | 1.83 | 2.685 (6) | 178 |
O1W—H1W2···O1 | 0.82 | 1.94 | 2.754 (4) | 173 |
O1W—H1W1···O4i | 0.82 | 2.19 | 3.007 (6) | 173 |
Symmetry codes: (i) x, −y+1, z+1/2; (iii) −x+3/2, y−1/2, −z+1/2; (iv) −x+1, −y+1, −z+1; (v) −x+3/2, −y+1/2, −z+1; (vi) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Mn(C12H6O4)(C19H12N4O)2]·0.5C12H8O4·H2O |
Mr | 1019.87 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 295 |
a, b, c (Å) | 48.398 (15), 9.089 (2), 20.598 (6) |
β (°) | 103.20 (1) |
V (Å3) | 8821 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.38 |
Crystal size (mm) | 0.31 × 0.25 × 0.18 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.820, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 40785, 10014, 5868 |
Rint | 0.084 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.170, 1.03 |
No. of reflections | 10014 |
No. of parameters | 717 |
No. of restraints | 116 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.35, −0.42 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003), publCIF (Westrip, 2008).
Mn1—O1 | 2.146 (2) | Mn1—N4 | 2.245 (3) |
Mn1—O3i | 2.108 (2) | Mn1—N5 | 2.265 (3) |
Mn1—N1 | 2.282 (3) | Mn1—N8 | 2.307 (3) |
O1—Mn1—O3i | 95.0 (1) | O3i—Mn1—N8 | 87.1 (1) |
O1—Mn1—N1 | 87.1 (1) | N1—Mn1—N4 | 73.4 (1) |
O1—Mn1—N4 | 97.6 (1) | N1—Mn1—N5 | 89.5 (1) |
O1—Mn1—N5 | 97.9 (1) | N1—Mn1—N8 | 93.4 (1) |
O1—Mn1—N8 | 169.9 (1) | N4—Mn1—N5 | 156.2 (1) |
O3i—Mn1—N1 | 165.2 (1) | N4—Mn1—N8 | 92.2 (1) |
O3i—Mn1—N4 | 91.8 (1) | N5—Mn1—N8 | 72.0 (1) |
O3i—Mn1—N5 | 104.8 (1) |
Symmetry code: (i) x, −y+1, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5O···N2ii | 0.82 | 1.93 | 2.737 (4) | 168 |
O6—H6O···O1Wiii | 0.82 | 1.85 | 2.656 (4) | 168 |
N3—H3N···O2iv | 0.86 | 1.97 | 2.813 (4) | 166 |
N6—H6N···O9 | 0.86 | 2.00 | 2.728 (6) | 142 |
N7—H7N···O10v | 0.86 | 1.83 | 2.685 (6) | 178 |
O1W—H1W2···O1 | 0.82 | 1.94 | 2.754 (4) | 173 |
O1W—H1W1···O4i | 0.82 | 2.19 | 3.007 (6) | 173 |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z+1; (iv) −x+3/2, −y+1/2, −z+1; (v) −x+1, −y, −z+1. |
Acknowledgements
The authors thank the Natural Science Foundation of Jilin Province (grant No. 20060516), the Doctoral Foundation of Jilin Normal University (grant No. 2006006), the Science and Technology Institute Foundation of Siping City (grant No. 2005016), the Subject and Base Construction Foundation of Jilin Normal University (grant No. 2006041) and the University of Malaya for supporting this work.
References
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There are manganese dicarboxylate adducts of complexes of 2-phenyl-1H-1,3,7,8-tetraazacyclopenta[l]phenanthrene (Li et al., 2008). The 4-hydroxy substituted ligand forms an adduct with manganese terephthalate (Che et al., 2006) that features a carboxylate-bridged chain motif. The title naphthalene-1,4-dicarboxylate adduct also adopts a layer motif. However, there is space between the chains that is large enough for a naphthalene-1,4-dicarboxylic acid molecule as well as a water molecule to fit in. Adjacent chains are linked by hydrogen bonds into a three-dimensional network.