metal-organic compounds
Poly[[μ4-naphthalene-1,4-dicarboxylato-κ4O:O′:O′′:O′′′-μ2-naphthalene-1,4-dicarboxylato-κ4O,O′:O′′,O′′′-bis(2-phenyl-1H-1,3,7,8-tetraazacyclopenta[l]phenanthrene-κ2N7,N8)dimanganese(II)] N,N-dimethylformamide solvate]
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
One of the two 1,4-dicarboxylate dianions in the title compound, [Mn2(C12H6O4)2(C19H12N4)2]·C3H7NO, uses its two carboxylate groups to chelate two N-heterocycle-chelated Mn atoms; the other 1,4-dicarboxylate dianion binds to four such metal centers. The octahedrally coordinated Mn atoms are linked through the two dianions into a layer motif; the dimethylformamide molecules occupy the spaces between adjacent layers. Ten C atoms and attached H atoms of one dianion are disordered equally over two positions.
Related literature
There are several studies of 2-phenyl-1H-1,3,7,8-tetraazacyclopenta[l]phenanthrene-chelated metal compounds; for the structures of the manganese dicarboxylate adducts, see: Che (2006); Che & Liu (2006); Wang et al. (2006); Zhang 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/S1600536808010787/rz2195sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010787/rz2195Isup2.hkl
Manganese dichloride dihydrate (0.1 mmol), naphthalene-1,4-dicarboxylic acid (0.1 mmol), 2-phenyl-1H-1,3,7,8-tetraazacyclopenta[l]phenanthrene (0.1 mmol), water (8 ml) and DMF (4 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-dicarboxylate dianion that is involved in µ4-bridging is disordered over two positions in the fused-ring portion. This was refined as two rigid naphthalene groups of 1.39 Å sides; the occupancy was arbitrarily set as 0.5 as this could not be refined. The C1–C11 and C1'–C11 distances were restrained to within 0.01 Å of each other, as were the C4–C12 and C4'–C12 pair of distances. The anisotropic displacement factors of the two fused-rings were restrained to be nearly isotropic.
The carbon-bound H atoms were placed in calculated positions [C–H 0.93, N–H 0.86 Å and Uiso(H) 1.2Ueq(C,N)], and were included in the
in the riding-model approximation.The final difference Fourier map had a large peak at 2.8 Å from O7, 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).[Mn2(C12H6O4)2(C19H12N4)2]·C3H7NO | Z = 2 |
Mr = 1203.96 | F(000) = 1236 |
Triclinic, P1 | Dx = 1.457 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.240 (2) Å | Cell parameters from 15789 reflections |
b = 14.852 (5) Å | θ = 3.0–27.5° |
c = 21.921 (5) Å | µ = 0.53 mm−1 |
α = 105.72 (1)° | T = 295 K |
β = 100.48 (1)° | Block, colorless |
γ = 101.67 (1)° | 0.26 × 0.16 × 0.12 mm |
V = 2745.0 (13) Å3 |
Rigaku R-AXIS RAPID diffractometer | 9443 independent reflections |
Radiation source: fine-focus sealed tube | 4800 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.084 |
Detector resolution: 10 pixels mm-1 | θmax = 25.0°, θmin = 3.0° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −17→17 |
Tmin = 0.760, Tmax = 0.940 | l = −26→26 |
21501 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)] = 0.080 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.262 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.1308P)2 + 1.0767P] where P = (Fo2 + 2Fc2)/3 |
9443 reflections | (Δ/σ)max = 0.001 |
810 parameters | Δρmax = 1.74 e Å−3 |
158 restraints | Δρmin = −0.48 e Å−3 |
[Mn2(C12H6O4)2(C19H12N4)2]·C3H7NO | γ = 101.67 (1)° |
Mr = 1203.96 | V = 2745.0 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.240 (2) Å | Mo Kα radiation |
b = 14.852 (5) Å | µ = 0.53 mm−1 |
c = 21.921 (5) Å | T = 295 K |
α = 105.72 (1)° | 0.26 × 0.16 × 0.12 mm |
β = 100.48 (1)° |
Rigaku R-AXIS RAPID diffractometer | 9443 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 4800 reflections with I > 2σ(I) |
Tmin = 0.760, Tmax = 0.940 | Rint = 0.084 |
21501 measured reflections |
R[F2 > 2σ(F2)] = 0.080 | 158 restraints |
wR(F2) = 0.262 | H-atom parameters constrained |
S = 1.06 | Δρmax = 1.74 e Å−3 |
9443 reflections | Δρmin = −0.48 e Å−3 |
810 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Mn1 | 0.80675 (10) | 0.75810 (7) | 0.69248 (5) | 0.0344 (3) | |
Mn2 | 1.06512 (11) | 0.08617 (8) | 0.75021 (6) | 0.0431 (3) | |
O1 | 0.8244 (5) | −0.1078 (3) | 0.7625 (2) | 0.0484 (13) | |
O2 | 0.8416 (5) | 0.0418 (4) | 0.7602 (3) | 0.0721 (19) | |
O3 | 0.0485 (5) | −0.0465 (4) | 0.6792 (3) | 0.0523 (14) | |
O4 | 0.0263 (5) | −0.1993 (4) | 0.6783 (3) | 0.0539 (14) | |
O5 | 0.8422 (5) | 0.5979 (3) | 0.6470 (2) | 0.0394 (11) | |
O6 | 0.8715 (5) | 0.6725 (4) | 0.7537 (2) | 0.0464 (13) | |
O7 | 1.0143 (5) | 0.1880 (4) | 0.6976 (3) | 0.0500 (13) | |
O8 | 1.0396 (5) | 0.2427 (4) | 0.8038 (2) | 0.0445 (12) | |
N1 | 0.6616 (5) | 0.7650 (4) | 0.6015 (3) | 0.0358 (13) | |
N2 | 0.1203 (6) | 0.6871 (5) | 0.4819 (3) | 0.0418 (15) | |
N3 | 0.0391 (6) | 0.6310 (4) | 0.5578 (3) | 0.0372 (14) | |
H3N | −0.0221 | 0.6062 | 0.5778 | 0.045* | |
N4 | 0.5621 (6) | 0.6932 (4) | 0.6907 (3) | 0.0335 (13) | |
N5 | 1.2081 (6) | 0.0765 (4) | 0.8419 (3) | 0.0433 (15) | |
N6 | 1.7453 (6) | 0.1593 (5) | 0.9659 (3) | 0.0479 (16) | |
N7 | 1.8308 (6) | 0.2076 (4) | 0.8873 (3) | 0.0439 (15) | |
H7N | 1.8936 | 0.2302 | 0.8671 | 0.053* | |
N8 | 1.3130 (6) | 0.1489 (4) | 0.7526 (3) | 0.0427 (15) | |
C1 | 0.5938 (5) | −0.0627 (9) | 0.7341 (5) | 0.027 (8) | 0.50 |
C2 | 0.5072 (7) | −0.1025 (11) | 0.7707 (5) | 0.029 (6) | 0.50 |
H2 | 0.5551 | −0.1156 | 0.8072 | 0.035* | 0.50 |
C3 | 0.3489 (7) | −0.1228 (11) | 0.7526 (5) | 0.037 (5) | 0.50 |
H3 | 0.2910 | −0.1494 | 0.7771 | 0.045* | 0.50 |
C4 | 0.2773 (5) | −0.1033 (10) | 0.6980 (5) | 0.048 (8) | 0.50 |
C5 | 0.3640 (5) | −0.0635 (7) | 0.6615 (4) | 0.048 (10) | 0.50 |
C6 | 0.5223 (5) | −0.0432 (7) | 0.6795 (4) | 0.034 (10) | 0.50 |
C7 | 0.6089 (7) | −0.0034 (8) | 0.6429 (5) | 0.054 (4) | 0.50 |
H7 | 0.7148 | 0.0102 | 0.6550 | 0.064* | 0.50 |
C8 | 0.5373 (11) | 0.0161 (8) | 0.5883 (4) | 0.071 (5) | 0.50 |
H8 | 0.5953 | 0.0428 | 0.5639 | 0.085* | 0.50 |
C9 | 0.3791 (11) | −0.0041 (8) | 0.5703 (4) | 0.067 (5) | 0.50 |
H9 | 0.3312 | 0.0089 | 0.5338 | 0.081* | 0.50 |
C10 | 0.2924 (8) | −0.0439 (9) | 0.6069 (4) | 0.063 (5) | 0.50 |
H10 | 0.1865 | −0.0575 | 0.5948 | 0.076* | 0.50 |
C1' | 0.5934 (5) | −0.0562 (9) | 0.7394 (4) | 0.047 (11) | 0.50 |
C2' | 0.5185 (7) | −0.0413 (10) | 0.6835 (5) | 0.048 (13) | 0.50 |
H2' | 0.5741 | −0.0190 | 0.6567 | 0.058* | 0.50 |
C3' | 0.3604 (7) | −0.0597 (9) | 0.6676 (4) | 0.029 (8) | 0.50 |
H3' | 0.3102 | −0.0497 | 0.6301 | 0.035* | 0.50 |
C4' | 0.2772 (5) | −0.0931 (8) | 0.7076 (4) | 0.021 (5) | 0.50 |
C5' | 0.3521 (5) | −0.1080 (5) | 0.7635 (3) | 0.028 (5) | 0.50 |
C6' | 0.5103 (5) | −0.0895 (6) | 0.7794 (3) | 0.040 (8) | 0.50 |
C7' | 0.5852 (6) | −0.1045 (7) | 0.8353 (4) | 0.039 (3) | 0.50 |
H7' | 0.6910 | −0.0921 | 0.8460 | 0.047* | 0.50 |
C8' | 0.5020 (9) | −0.1378 (6) | 0.8753 (3) | 0.044 (4) | 0.50 |
H8' | 0.5522 | −0.1478 | 0.9128 | 0.053* | 0.50 |
C9' | 0.3439 (9) | −0.1562 (6) | 0.8594 (4) | 0.046 (4) | 0.50 |
H9' | 0.2883 | −0.1786 | 0.8862 | 0.055* | 0.50 |
C10' | 0.2690 (6) | −0.1413 (6) | 0.8035 (4) | 0.042 (3) | 0.50 |
H10' | 0.1632 | −0.1537 | 0.7929 | 0.051* | 0.50 |
C11 | 0.7665 (7) | −0.0412 (5) | 0.7541 (4) | 0.0456 (19) | |
C12 | 0.1025 (8) | −0.1168 (6) | 0.6854 (3) | 0.0422 (18) | |
C13 | 0.8782 (7) | 0.6019 (5) | 0.7074 (4) | 0.0394 (17) | |
C14 | 0.9218 (7) | 0.5171 (5) | 0.7226 (3) | 0.0370 (16) | |
C15 | 1.0253 (7) | 0.5249 (5) | 0.7819 (3) | 0.0346 (16) | |
C16 | 1.0953 (8) | 0.6157 (5) | 0.8332 (4) | 0.0485 (19) | |
H16 | 1.0697 | 0.6716 | 0.8290 | 0.058* | |
C17 | 1.1988 (9) | 0.6212 (6) | 0.8881 (4) | 0.056 (2) | |
H17 | 1.2416 | 0.6804 | 0.9212 | 0.067* | |
C18 | 1.2410 (9) | 0.5380 (7) | 0.8948 (4) | 0.063 (2) | |
H18 | 1.3150 | 0.5432 | 0.9315 | 0.075* | |
C19 | 1.1752 (8) | 0.4502 (6) | 0.8485 (4) | 0.0492 (19) | |
H19 | 1.2030 | 0.3958 | 0.8545 | 0.059* | |
C20 | 1.0646 (7) | 0.4397 (5) | 0.7909 (3) | 0.0369 (16) | |
C21 | 0.9922 (7) | 0.3487 (5) | 0.7412 (3) | 0.0349 (16) | |
C22 | 0.8966 (8) | 0.3436 (5) | 0.6850 (4) | 0.0407 (17) | |
H22 | 0.8517 | 0.2838 | 0.6527 | 0.049* | |
C23 | 0.8646 (7) | 0.4275 (5) | 0.6751 (3) | 0.0388 (17) | |
H23 | 0.8027 | 0.4226 | 0.6352 | 0.047* | |
C24 | 1.0185 (7) | 0.2543 (5) | 0.7487 (4) | 0.0402 (17) | |
C25 | 0.7115 (7) | 0.8015 (5) | 0.5574 (4) | 0.0444 (18) | |
H25 | 0.8161 | 0.8266 | 0.5646 | 0.053* | |
C26 | 0.6146 (8) | 0.8038 (6) | 0.5007 (4) | 0.052 (2) | |
H26 | 0.6547 | 0.8283 | 0.4707 | 0.063* | |
C27 | 0.4607 (8) | 0.7695 (6) | 0.4904 (3) | 0.0472 (19) | |
H27 | 0.3947 | 0.7705 | 0.4532 | 0.057* | |
C28 | 0.4023 (7) | 0.7326 (5) | 0.5366 (3) | 0.0340 (15) | |
C29 | 0.5081 (7) | 0.7313 (5) | 0.5913 (3) | 0.0304 (14) | |
C30 | 0.2444 (7) | 0.6954 (5) | 0.5310 (3) | 0.0360 (16) | |
C31 | −0.0010 (7) | 0.6479 (5) | 0.4995 (3) | 0.0404 (17) | |
C32 | −0.1577 (7) | 0.6204 (5) | 0.4597 (3) | 0.0407 (17) | |
C33 | −0.1849 (8) | 0.6449 (6) | 0.4017 (4) | 0.054 (2) | |
H33 | −0.1045 | 0.6802 | 0.3906 | 0.065* | |
C34 | −0.3294 (9) | 0.6169 (7) | 0.3616 (4) | 0.062 (2) | |
H34 | −0.3451 | 0.6322 | 0.3229 | 0.074* | |
C35 | −0.4512 (8) | 0.5666 (6) | 0.3772 (4) | 0.057 (2) | |
H35 | −0.5489 | 0.5482 | 0.3498 | 0.068* | |
C36 | −0.4247 (8) | 0.5435 (6) | 0.4359 (4) | 0.058 (2) | |
H36 | −0.5062 | 0.5104 | 0.4477 | 0.070* | |
C37 | −0.2806 (7) | 0.5693 (6) | 0.4757 (4) | 0.0454 (18) | |
H37 | −0.2649 | 0.5525 | 0.5138 | 0.055* | |
C38 | 0.1968 (6) | 0.6614 (5) | 0.5786 (3) | 0.0330 (15) | |
C39 | 0.2984 (7) | 0.6593 (5) | 0.6347 (3) | 0.0324 (15) | |
C40 | 0.4544 (7) | 0.6934 (5) | 0.6397 (3) | 0.0344 (15) | |
C41 | 0.2561 (8) | 0.6218 (5) | 0.6840 (4) | 0.0447 (18) | |
H41 | 0.1537 | 0.5966 | 0.6814 | 0.054* | |
C42 | 0.3656 (7) | 0.6229 (6) | 0.7346 (3) | 0.0441 (18) | |
H42 | 0.3389 | 0.6003 | 0.7678 | 0.053* | |
C43 | 0.5183 (7) | 0.6582 (5) | 0.7367 (3) | 0.0406 (17) | |
H43 | 0.5928 | 0.6574 | 0.7712 | 0.049* | |
C44 | 1.1542 (8) | 0.0416 (6) | 0.8854 (4) | 0.059 (2) | |
H44 | 1.0494 | 0.0165 | 0.8777 | 0.070* | |
C45 | 1.2488 (10) | 0.0416 (7) | 0.9412 (4) | 0.072 (3) | |
H45 | 1.2068 | 0.0186 | 0.9714 | 0.086* | |
C46 | 1.4035 (9) | 0.0746 (7) | 0.9535 (4) | 0.064 (2) | |
H46 | 1.4675 | 0.0727 | 0.9909 | 0.076* | |
C47 | 1.4632 (7) | 0.1115 (5) | 0.9083 (4) | 0.0427 (18) | |
C48 | 1.3611 (7) | 0.1117 (5) | 0.8531 (3) | 0.0385 (17) | |
C49 | 1.6241 (7) | 0.1468 (5) | 0.9147 (4) | 0.0435 (18) | |
C50 | 1.8678 (8) | 0.1949 (5) | 0.9482 (3) | 0.0425 (18) | |
C51 | 2.0230 (8) | 0.2242 (6) | 0.9890 (4) | 0.0481 (19) | |
C52 | 2.0480 (9) | 0.2083 (7) | 1.0480 (4) | 0.067 (3) | |
H52 | 1.9674 | 0.1757 | 1.0606 | 0.081* | |
C53 | 2.1936 (11) | 0.2406 (8) | 1.0891 (4) | 0.085 (3) | |
H53 | 2.2091 | 0.2319 | 1.1300 | 0.103* | |
C54 | 2.3144 (10) | 0.2850 (8) | 1.0708 (5) | 0.079 (3) | |
H54 | 2.4119 | 0.3047 | 1.0985 | 0.095* | |
C55 | 2.2923 (9) | 0.3005 (7) | 1.0116 (5) | 0.075 (3) | |
H55 | 2.3744 | 0.3301 | 0.9985 | 0.090* | |
C56 | 2.1443 (9) | 0.2713 (7) | 0.9708 (4) | 0.063 (2) | |
H56 | 2.1278 | 0.2839 | 0.9311 | 0.075* | |
C57 | 1.6738 (7) | 0.1767 (5) | 0.8654 (3) | 0.0386 (17) | |
C58 | 1.5753 (8) | 0.1778 (5) | 0.8082 (4) | 0.0420 (17) | |
C59 | 1.4184 (7) | 0.1474 (5) | 0.8023 (3) | 0.0336 (15) | |
C60 | 1.6205 (8) | 0.2092 (6) | 0.7593 (4) | 0.055 (2) | |
H60 | 1.7237 | 0.2287 | 0.7609 | 0.066* | |
C61 | 1.5131 (9) | 0.2115 (6) | 0.7086 (4) | 0.058 (2) | |
H61 | 1.5414 | 0.2336 | 0.6755 | 0.070* | |
C62 | 1.3589 (8) | 0.1797 (6) | 0.7075 (4) | 0.053 (2) | |
H62 | 1.2856 | 0.1806 | 0.6726 | 0.064* | |
O9 | 2.5478 (19) | 0.3811 (10) | 0.9394 (7) | 0.251 (7) | |
N9 | 2.6817 (9) | 0.4487 (5) | 0.8833 (4) | 0.081 (2) | |
C63 | 2.5473 (15) | 0.4057 (7) | 0.8923 (7) | 0.148 (6) | |
H63 | 2.4561 | 0.3956 | 0.8620 | 0.178* | |
C64 | 2.8345 (11) | 0.4717 (9) | 0.9235 (6) | 0.120 (4) | |
H64A | 2.8304 | 0.4595 | 0.9641 | 0.181* | |
H64B | 2.8841 | 0.5388 | 0.9322 | 0.181* | |
H64C | 2.8908 | 0.4320 | 0.9010 | 0.181* | |
C65 | 2.6539 (17) | 0.4727 (9) | 0.8232 (5) | 0.136 (5) | |
H65A | 2.5459 | 0.4589 | 0.8055 | 0.204* | |
H65B | 2.6969 | 0.4346 | 0.7921 | 0.204* | |
H65C | 2.7004 | 0.5404 | 0.8321 | 0.204* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.0223 (5) | 0.0271 (6) | 0.0533 (7) | 0.0068 (4) | 0.0067 (5) | 0.0140 (5) |
Mn2 | 0.0265 (6) | 0.0289 (7) | 0.0766 (8) | 0.0103 (5) | 0.0118 (5) | 0.0196 (6) |
O1 | 0.033 (3) | 0.033 (3) | 0.070 (3) | 0.012 (2) | 0.003 (2) | 0.006 (3) |
O2 | 0.029 (3) | 0.034 (3) | 0.151 (6) | 0.009 (3) | 0.035 (3) | 0.016 (4) |
O3 | 0.035 (3) | 0.038 (3) | 0.083 (4) | 0.016 (2) | 0.008 (3) | 0.019 (3) |
O4 | 0.029 (3) | 0.031 (3) | 0.101 (4) | 0.007 (2) | 0.025 (3) | 0.016 (3) |
O5 | 0.037 (3) | 0.040 (3) | 0.046 (3) | 0.011 (2) | 0.008 (2) | 0.024 (2) |
O6 | 0.051 (3) | 0.040 (3) | 0.059 (3) | 0.025 (3) | 0.017 (3) | 0.020 (3) |
O7 | 0.052 (3) | 0.033 (3) | 0.066 (3) | 0.020 (3) | 0.009 (3) | 0.016 (3) |
O8 | 0.042 (3) | 0.042 (3) | 0.063 (3) | 0.018 (2) | 0.016 (3) | 0.030 (3) |
N1 | 0.026 (3) | 0.035 (4) | 0.044 (3) | 0.005 (2) | 0.009 (3) | 0.012 (3) |
N2 | 0.027 (3) | 0.060 (4) | 0.037 (3) | 0.008 (3) | 0.004 (3) | 0.018 (3) |
N3 | 0.023 (3) | 0.048 (4) | 0.040 (3) | 0.007 (3) | 0.007 (3) | 0.017 (3) |
N4 | 0.029 (3) | 0.027 (3) | 0.038 (3) | 0.005 (2) | 0.000 (3) | 0.008 (3) |
N5 | 0.032 (3) | 0.031 (4) | 0.066 (4) | 0.006 (3) | 0.013 (3) | 0.014 (3) |
N6 | 0.040 (3) | 0.051 (4) | 0.053 (4) | 0.013 (3) | 0.013 (3) | 0.014 (3) |
N7 | 0.030 (3) | 0.038 (4) | 0.058 (4) | 0.006 (3) | 0.010 (3) | 0.007 (3) |
N8 | 0.028 (3) | 0.038 (4) | 0.065 (4) | 0.009 (3) | 0.011 (3) | 0.021 (3) |
C1 | 0.015 (10) | 0.023 (10) | 0.042 (10) | 0.006 (7) | 0.014 (7) | 0.003 (6) |
C2 | 0.026 (8) | 0.017 (7) | 0.036 (8) | 0.004 (6) | 0.000 (6) | 0.002 (6) |
C3 | 0.034 (9) | 0.019 (7) | 0.049 (8) | 0.001 (6) | 0.013 (7) | −0.003 (6) |
C4 | 0.050 (11) | 0.036 (11) | 0.053 (9) | 0.012 (8) | 0.008 (8) | 0.008 (7) |
C5 | 0.045 (13) | 0.047 (13) | 0.055 (12) | 0.013 (8) | 0.013 (9) | 0.020 (8) |
C6 | 0.023 (12) | 0.030 (13) | 0.048 (12) | 0.002 (7) | 0.018 (8) | 0.011 (7) |
C7 | 0.053 (7) | 0.049 (8) | 0.061 (8) | 0.011 (6) | 0.018 (6) | 0.021 (6) |
C8 | 0.068 (8) | 0.076 (9) | 0.073 (8) | 0.016 (7) | 0.018 (7) | 0.032 (7) |
C9 | 0.059 (8) | 0.076 (9) | 0.075 (8) | 0.027 (7) | 0.019 (7) | 0.030 (7) |
C10 | 0.054 (8) | 0.070 (9) | 0.069 (8) | 0.019 (7) | 0.015 (7) | 0.026 (7) |
C1' | 0.038 (13) | 0.035 (13) | 0.060 (13) | 0.010 (9) | 0.008 (9) | 0.004 (8) |
C2' | 0.039 (15) | 0.043 (15) | 0.061 (14) | 0.011 (9) | 0.016 (9) | 0.011 (8) |
C3' | 0.015 (9) | 0.029 (10) | 0.044 (10) | 0.015 (7) | 0.005 (7) | 0.009 (6) |
C4' | 0.010 (7) | 0.008 (7) | 0.045 (8) | 0.005 (5) | 0.013 (6) | 0.003 (5) |
C5' | 0.025 (8) | 0.016 (8) | 0.040 (8) | 0.010 (6) | 0.007 (6) | 0.001 (6) |
C6' | 0.043 (10) | 0.034 (10) | 0.047 (10) | 0.013 (7) | 0.017 (8) | 0.011 (7) |
C7' | 0.038 (6) | 0.034 (7) | 0.045 (7) | 0.015 (5) | 0.006 (5) | 0.009 (5) |
C8' | 0.041 (6) | 0.042 (7) | 0.051 (7) | 0.015 (6) | 0.010 (6) | 0.015 (6) |
C9' | 0.054 (7) | 0.035 (7) | 0.053 (7) | 0.009 (6) | 0.026 (6) | 0.014 (6) |
C10' | 0.037 (6) | 0.036 (7) | 0.054 (7) | 0.013 (5) | 0.017 (6) | 0.008 (6) |
C11 | 0.026 (3) | 0.029 (4) | 0.075 (5) | 0.004 (3) | 0.012 (4) | 0.009 (4) |
C12 | 0.035 (4) | 0.043 (5) | 0.047 (4) | 0.012 (4) | 0.011 (3) | 0.010 (4) |
C13 | 0.028 (3) | 0.036 (4) | 0.063 (5) | 0.008 (3) | 0.019 (4) | 0.024 (4) |
C14 | 0.032 (4) | 0.032 (4) | 0.052 (4) | 0.013 (3) | 0.016 (3) | 0.014 (3) |
C15 | 0.028 (3) | 0.040 (4) | 0.040 (4) | 0.010 (3) | 0.011 (3) | 0.015 (3) |
C16 | 0.052 (5) | 0.033 (5) | 0.059 (5) | 0.017 (4) | 0.009 (4) | 0.011 (4) |
C17 | 0.062 (5) | 0.042 (5) | 0.052 (5) | 0.014 (4) | 0.004 (4) | 0.004 (4) |
C18 | 0.045 (5) | 0.070 (7) | 0.061 (5) | 0.010 (5) | −0.008 (4) | 0.020 (5) |
C19 | 0.041 (4) | 0.047 (5) | 0.057 (5) | 0.015 (4) | −0.004 (4) | 0.021 (4) |
C20 | 0.033 (3) | 0.035 (4) | 0.053 (4) | 0.014 (3) | 0.017 (3) | 0.022 (4) |
C21 | 0.030 (3) | 0.030 (4) | 0.048 (4) | 0.009 (3) | 0.013 (3) | 0.015 (3) |
C22 | 0.047 (4) | 0.028 (4) | 0.052 (4) | 0.016 (3) | 0.013 (4) | 0.017 (3) |
C23 | 0.029 (3) | 0.050 (5) | 0.040 (4) | 0.012 (3) | 0.008 (3) | 0.018 (4) |
C24 | 0.029 (4) | 0.033 (4) | 0.065 (5) | 0.015 (3) | 0.014 (4) | 0.021 (4) |
C25 | 0.027 (3) | 0.050 (5) | 0.060 (5) | 0.008 (3) | 0.019 (4) | 0.019 (4) |
C26 | 0.047 (4) | 0.063 (6) | 0.050 (5) | 0.011 (4) | 0.015 (4) | 0.025 (4) |
C27 | 0.049 (4) | 0.060 (6) | 0.039 (4) | 0.018 (4) | 0.013 (4) | 0.023 (4) |
C28 | 0.031 (3) | 0.034 (4) | 0.038 (4) | 0.009 (3) | 0.012 (3) | 0.011 (3) |
C29 | 0.025 (3) | 0.028 (4) | 0.036 (4) | 0.004 (3) | 0.005 (3) | 0.011 (3) |
C30 | 0.030 (4) | 0.041 (4) | 0.033 (4) | 0.009 (3) | 0.007 (3) | 0.008 (3) |
C31 | 0.029 (4) | 0.048 (5) | 0.041 (4) | 0.013 (3) | 0.008 (3) | 0.010 (4) |
C32 | 0.030 (4) | 0.044 (5) | 0.040 (4) | 0.010 (3) | 0.005 (3) | 0.003 (3) |
C33 | 0.042 (4) | 0.064 (6) | 0.057 (5) | 0.011 (4) | 0.011 (4) | 0.023 (4) |
C34 | 0.045 (5) | 0.088 (7) | 0.057 (5) | 0.029 (5) | −0.001 (4) | 0.030 (5) |
C35 | 0.027 (4) | 0.065 (6) | 0.067 (5) | 0.016 (4) | −0.001 (4) | 0.010 (5) |
C36 | 0.037 (4) | 0.060 (6) | 0.069 (6) | 0.007 (4) | 0.009 (4) | 0.013 (5) |
C37 | 0.034 (4) | 0.049 (5) | 0.052 (4) | 0.009 (3) | 0.007 (4) | 0.019 (4) |
C38 | 0.020 (3) | 0.042 (4) | 0.036 (4) | 0.011 (3) | 0.002 (3) | 0.011 (3) |
C39 | 0.026 (3) | 0.027 (4) | 0.043 (4) | 0.007 (3) | 0.007 (3) | 0.009 (3) |
C40 | 0.034 (4) | 0.023 (4) | 0.039 (4) | 0.003 (3) | 0.005 (3) | 0.003 (3) |
C41 | 0.033 (4) | 0.048 (5) | 0.060 (5) | 0.007 (3) | 0.019 (4) | 0.026 (4) |
C42 | 0.036 (4) | 0.060 (5) | 0.040 (4) | 0.009 (4) | 0.008 (3) | 0.024 (4) |
C43 | 0.027 (3) | 0.051 (5) | 0.042 (4) | 0.007 (3) | 0.002 (3) | 0.019 (4) |
C44 | 0.033 (4) | 0.066 (6) | 0.085 (6) | 0.009 (4) | 0.021 (5) | 0.037 (5) |
C45 | 0.056 (5) | 0.102 (8) | 0.075 (6) | 0.018 (5) | 0.032 (5) | 0.049 (6) |
C46 | 0.056 (5) | 0.084 (7) | 0.062 (5) | 0.020 (5) | 0.021 (5) | 0.033 (5) |
C47 | 0.032 (4) | 0.041 (5) | 0.056 (5) | 0.007 (3) | 0.017 (4) | 0.015 (4) |
C48 | 0.029 (3) | 0.024 (4) | 0.054 (4) | 0.003 (3) | 0.011 (3) | 0.001 (3) |
C49 | 0.033 (4) | 0.042 (5) | 0.051 (4) | 0.016 (3) | 0.005 (4) | 0.007 (4) |
C50 | 0.034 (4) | 0.045 (5) | 0.045 (4) | 0.011 (3) | 0.009 (3) | 0.009 (4) |
C51 | 0.038 (4) | 0.053 (5) | 0.045 (4) | 0.012 (4) | 0.006 (4) | 0.006 (4) |
C52 | 0.042 (5) | 0.090 (8) | 0.057 (5) | 0.010 (5) | 0.008 (4) | 0.013 (5) |
C53 | 0.066 (6) | 0.131 (10) | 0.034 (5) | 0.015 (6) | −0.004 (5) | 0.006 (5) |
C54 | 0.037 (5) | 0.105 (9) | 0.070 (7) | 0.008 (5) | −0.006 (5) | 0.010 (6) |
C55 | 0.039 (5) | 0.084 (8) | 0.084 (7) | 0.002 (5) | 0.013 (5) | 0.011 (6) |
C56 | 0.046 (5) | 0.064 (6) | 0.067 (6) | 0.010 (4) | 0.002 (4) | 0.015 (5) |
C57 | 0.030 (4) | 0.031 (4) | 0.053 (4) | 0.012 (3) | 0.012 (4) | 0.008 (3) |
C58 | 0.037 (4) | 0.034 (4) | 0.057 (5) | 0.006 (3) | 0.017 (4) | 0.015 (4) |
C59 | 0.032 (3) | 0.023 (4) | 0.044 (4) | 0.008 (3) | 0.006 (3) | 0.009 (3) |
C60 | 0.026 (4) | 0.063 (6) | 0.078 (6) | 0.008 (4) | 0.010 (4) | 0.031 (5) |
C61 | 0.047 (5) | 0.056 (6) | 0.082 (6) | 0.007 (4) | 0.019 (5) | 0.041 (5) |
C62 | 0.038 (4) | 0.050 (5) | 0.077 (6) | 0.007 (4) | 0.015 (4) | 0.032 (5) |
O9 | 0.266 (11) | 0.249 (11) | 0.242 (10) | 0.055 (8) | 0.089 (8) | 0.080 (8) |
N9 | 0.072 (5) | 0.072 (5) | 0.096 (5) | 0.011 (4) | 0.031 (4) | 0.019 (4) |
C63 | 0.159 (8) | 0.143 (8) | 0.145 (8) | 0.046 (6) | 0.043 (6) | 0.044 (6) |
C64 | 0.086 (9) | 0.110 (11) | 0.142 (11) | 0.010 (8) | 0.012 (8) | 0.027 (9) |
C65 | 0.180 (9) | 0.124 (9) | 0.122 (8) | 0.042 (7) | 0.061 (7) | 0.052 (7) |
Mn1—O1i | 2.115 (5) | C17—C18 | 1.406 (11) |
Mn1—O4ii | 2.105 (4) | C17—H17 | 0.9300 |
Mn1—O5 | 2.431 (5) | C18—C19 | 1.355 (11) |
Mn1—O6 | 2.171 (5) | C18—H18 | 0.9300 |
Mn1—N1 | 2.232 (5) | C19—C20 | 1.421 (9) |
Mn1—N4 | 2.259 (5) | C19—H19 | 0.9300 |
Mn2—O2 | 2.107 (5) | C20—C21 | 1.426 (9) |
Mn2—O3iii | 2.112 (5) | C21—C22 | 1.351 (9) |
Mn2—O7 | 2.208 (5) | C21—C24 | 1.516 (9) |
Mn2—O8 | 2.384 (5) | C22—C23 | 1.400 (9) |
Mn2—N5 | 2.252 (6) | C22—H22 | 0.9300 |
Mn2—N8 | 2.277 (5) | C23—H23 | 0.9300 |
O1—C11 | 1.255 (8) | C25—C26 | 1.407 (10) |
O2—C11 | 1.246 (8) | C25—H25 | 0.9300 |
O3—C12 | 1.272 (8) | C26—C27 | 1.363 (9) |
O4—C12 | 1.237 (8) | C26—H26 | 0.9300 |
O4—Mn1iv | 2.105 (4) | C27—C28 | 1.414 (9) |
O5—C13 | 1.285 (8) | C27—H27 | 0.9300 |
O6—C13 | 1.268 (8) | C28—C29 | 1.410 (9) |
O7—C24 | 1.264 (8) | C28—C30 | 1.421 (8) |
O8—C24 | 1.252 (8) | C29—C40 | 1.445 (9) |
N1—C25 | 1.335 (8) | C30—C38 | 1.378 (9) |
N1—C29 | 1.360 (7) | C31—C32 | 1.460 (9) |
N2—C31 | 1.325 (8) | C32—C37 | 1.389 (9) |
N2—C30 | 1.381 (8) | C32—C33 | 1.408 (10) |
N3—C31 | 1.370 (9) | C33—C34 | 1.371 (10) |
N3—C38 | 1.384 (7) | C33—H33 | 0.9300 |
N3—H3N | 0.8600 | C34—C35 | 1.371 (11) |
N4—C43 | 1.342 (8) | C34—H34 | 0.9300 |
N4—C40 | 1.357 (8) | C35—C36 | 1.411 (11) |
N5—C44 | 1.327 (9) | C35—H35 | 0.9300 |
N5—C48 | 1.356 (8) | C36—C37 | 1.367 (10) |
N6—C50 | 1.319 (8) | C36—H36 | 0.9300 |
N6—C49 | 1.375 (9) | C37—H37 | 0.9300 |
N7—C57 | 1.380 (8) | C38—C39 | 1.416 (9) |
N7—C50 | 1.390 (9) | C39—C40 | 1.401 (8) |
N7—H7N | 0.8600 | C39—C41 | 1.423 (9) |
N8—C62 | 1.298 (9) | C41—C42 | 1.353 (9) |
N8—C59 | 1.331 (8) | C41—H41 | 0.9300 |
C1—C2 | 1.3900 | C42—C43 | 1.390 (9) |
C1—C6 | 1.3900 | C42—H42 | 0.9300 |
C1—C11 | 1.517 (8) | C43—H43 | 0.9300 |
C2—C3 | 1.3900 | C44—C45 | 1.370 (11) |
C2—H2 | 0.9300 | C44—H44 | 0.9300 |
C3—C4 | 1.3900 | C45—C46 | 1.365 (11) |
C3—H3 | 0.9300 | C45—H45 | 0.9300 |
C4—C5 | 1.3900 | C46—C47 | 1.399 (10) |
C4—C12 | 1.550 (8) | C46—H46 | 0.9300 |
C5—C6 | 1.3900 | C47—C48 | 1.393 (10) |
C5—C10 | 1.3900 | C47—C49 | 1.441 (9) |
C6—C7 | 1.3900 | C48—C59 | 1.490 (9) |
C7—C8 | 1.3900 | C49—C57 | 1.391 (10) |
C7—H7 | 0.9300 | C50—C51 | 1.454 (10) |
C8—C9 | 1.3900 | C51—C52 | 1.365 (11) |
C8—H8 | 0.9300 | C51—C56 | 1.379 (11) |
C9—C10 | 1.3900 | C52—C53 | 1.384 (11) |
C9—H9 | 0.9300 | C52—H52 | 0.9300 |
C10—H10 | 0.9300 | C53—C54 | 1.360 (13) |
C1'—C2' | 1.3900 | C53—H53 | 0.9300 |
C1'—C6' | 1.3900 | C54—C55 | 1.365 (13) |
C1'—C11 | 1.530 (8) | C54—H54 | 0.9300 |
C2'—C3' | 1.3900 | C55—C56 | 1.400 (11) |
C2'—H2' | 0.9300 | C55—H55 | 0.9300 |
C3'—C4' | 1.3900 | C56—H56 | 0.9300 |
C3'—H3' | 0.9300 | C57—C58 | 1.415 (10) |
C4'—C5' | 1.3900 | C58—C60 | 1.377 (10) |
C4'—C12 | 1.535 (8) | C58—C59 | 1.399 (9) |
C5'—C6' | 1.3900 | C60—C61 | 1.362 (11) |
C5'—C10' | 1.3900 | C60—H60 | 0.9300 |
C6'—C7' | 1.3900 | C61—C62 | 1.401 (10) |
C7'—C8' | 1.3900 | C61—H61 | 0.9300 |
C7'—H7' | 0.9300 | C62—H62 | 0.9300 |
C8'—C9' | 1.3900 | O9—C63 | 1.18 (2) |
C8'—H8' | 0.9300 | N9—C63 | 1.351 (9) |
C9'—C10' | 1.3900 | N9—C64 | 1.440 (8) |
C9'—H9' | 0.9300 | N9—C65 | 1.449 (8) |
C10'—H10' | 0.9300 | C63—H63 | 0.9300 |
C13—C14 | 1.499 (9) | C64—H64A | 0.9600 |
C14—C23 | 1.378 (9) | C64—H64B | 0.9600 |
C14—C15 | 1.427 (9) | C64—H64C | 0.9600 |
C15—C16 | 1.437 (10) | C65—H65A | 0.9600 |
C15—C20 | 1.438 (9) | C65—H65B | 0.9600 |
C16—C17 | 1.366 (10) | C65—H65C | 0.9600 |
C16—H16 | 0.9300 | ||
O4ii—Mn1—O1i | 94.88 (19) | C20—C19—H19 | 119.3 |
O4ii—Mn1—O6 | 94.6 (2) | C19—C20—C21 | 123.1 (6) |
O1i—Mn1—O6 | 102.2 (2) | C19—C20—C15 | 118.5 (7) |
O4ii—Mn1—N1 | 101.0 (2) | C21—C20—C15 | 118.3 (6) |
O1i—Mn1—N1 | 103.1 (2) | C22—C21—C20 | 120.8 (6) |
O6—Mn1—N1 | 148.9 (2) | C22—C21—C24 | 117.3 (7) |
O4ii—Mn1—N4 | 170.2 (2) | C20—C21—C24 | 121.9 (6) |
O1i—Mn1—N4 | 94.20 (18) | C21—C22—C23 | 120.6 (7) |
O6—Mn1—N4 | 87.09 (19) | C21—C22—H22 | 119.7 |
N1—Mn1—N4 | 73.34 (19) | C23—C22—H22 | 119.7 |
O4ii—Mn1—O5 | 81.46 (17) | C14—C23—C22 | 122.0 (7) |
O1i—Mn1—O5 | 159.11 (18) | C14—C23—H23 | 119.0 |
O6—Mn1—O5 | 57.90 (17) | C22—C23—H23 | 119.0 |
N1—Mn1—O5 | 97.75 (18) | O8—C24—O7 | 121.9 (6) |
N4—Mn1—O5 | 91.31 (17) | O8—C24—C21 | 120.3 (7) |
O2—Mn2—O3iii | 94.0 (2) | O7—C24—C21 | 117.8 (7) |
O2—Mn2—O7 | 95.2 (2) | O8—C24—Mn2 | 65.0 (4) |
O3iii—Mn2—O7 | 107.4 (2) | O7—C24—Mn2 | 56.9 (4) |
O2—Mn2—N5 | 102.3 (2) | C21—C24—Mn2 | 174.7 (5) |
O3iii—Mn2—N5 | 103.1 (2) | N1—C25—C26 | 123.6 (6) |
O7—Mn2—N5 | 143.5 (2) | N1—C25—H25 | 118.2 |
O2—Mn2—N8 | 172.5 (2) | C26—C25—H25 | 118.2 |
O3iii—Mn2—N8 | 93.1 (2) | C27—C26—C25 | 118.9 (7) |
O7—Mn2—N8 | 85.2 (2) | C27—C26—H26 | 120.6 |
N5—Mn2—N8 | 73.5 (2) | C25—C26—H26 | 120.6 |
O2—Mn2—O8 | 82.28 (18) | C26—C27—C28 | 119.6 (7) |
O3iii—Mn2—O8 | 163.32 (19) | C26—C27—H27 | 120.2 |
O7—Mn2—O8 | 57.07 (18) | C28—C27—H27 | 120.2 |
N5—Mn2—O8 | 93.55 (19) | C29—C28—C27 | 117.6 (6) |
N8—Mn2—O8 | 91.70 (19) | C29—C28—C30 | 118.0 (6) |
C11—O1—Mn1v | 127.7 (5) | C27—C28—C30 | 124.3 (6) |
C11—O2—Mn2 | 128.6 (5) | N1—C29—C28 | 122.9 (6) |
C12—O3—Mn2vi | 129.6 (5) | N1—C29—C40 | 117.3 (6) |
C12—O4—Mn1iv | 128.5 (4) | C28—C29—C40 | 119.8 (5) |
C13—O5—Mn1 | 83.7 (4) | C38—C30—N2 | 110.4 (5) |
C13—O6—Mn1 | 95.8 (4) | C38—C30—C28 | 120.7 (6) |
C24—O7—Mn2 | 94.4 (4) | N2—C30—C28 | 128.9 (6) |
C24—O8—Mn2 | 86.6 (4) | N2—C31—N3 | 111.7 (6) |
C25—N1—C29 | 117.5 (6) | N2—C31—C32 | 124.3 (6) |
C25—N1—Mn1 | 126.0 (4) | N3—C31—C32 | 123.8 (6) |
C29—N1—Mn1 | 116.5 (4) | C37—C32—C33 | 118.5 (6) |
C31—N2—C30 | 105.4 (5) | C37—C32—C31 | 123.1 (7) |
C31—N3—C38 | 107.0 (5) | C33—C32—C31 | 118.5 (6) |
C31—N3—H3N | 126.5 | C34—C33—C32 | 120.4 (7) |
C38—N3—H3N | 126.5 | C34—C33—H33 | 119.8 |
C43—N4—C40 | 119.2 (5) | C32—C33—H33 | 119.8 |
C43—N4—Mn1 | 124.8 (4) | C33—C34—C35 | 121.3 (8) |
C40—N4—Mn1 | 115.9 (4) | C33—C34—H34 | 119.3 |
C44—N5—C48 | 118.7 (7) | C35—C34—H34 | 119.3 |
C44—N5—Mn2 | 125.3 (5) | C34—C35—C36 | 118.4 (7) |
C48—N5—Mn2 | 116.0 (5) | C34—C35—H35 | 120.8 |
C50—N6—C49 | 105.2 (6) | C36—C35—H35 | 120.8 |
C57—N7—C50 | 106.7 (6) | C37—C36—C35 | 120.8 (7) |
C57—N7—H7N | 126.7 | C37—C36—H36 | 119.6 |
C50—N7—H7N | 126.7 | C35—C36—H36 | 119.6 |
C62—N8—C59 | 118.0 (6) | C36—C37—C32 | 120.6 (7) |
C62—N8—Mn2 | 125.3 (5) | C36—C37—H37 | 119.7 |
C59—N8—Mn2 | 116.5 (4) | C32—C37—H37 | 119.7 |
C2—C1—C6 | 120.0 | C30—C38—N3 | 105.5 (5) |
C2—C1—C11 | 119.5 (5) | C30—C38—C39 | 123.4 (6) |
C6—C1—C11 | 120.5 (5) | N3—C38—C39 | 131.0 (6) |
C1—C2—C3 | 120.0 | C40—C39—C38 | 116.2 (6) |
C1—C2—H2 | 120.0 | C40—C39—C41 | 117.8 (6) |
C3—C2—H2 | 120.0 | C38—C39—C41 | 125.9 (6) |
C4—C3—C2 | 120.0 | N4—C40—C39 | 121.4 (6) |
C4—C3—H3 | 120.0 | N4—C40—C29 | 116.9 (5) |
C2—C3—H3 | 120.0 | C39—C40—C29 | 121.8 (6) |
C3—C4—C5 | 120.0 | C42—C41—C39 | 119.7 (6) |
C3—C4—C12 | 117.1 (5) | C42—C41—H41 | 120.1 |
C5—C4—C12 | 122.6 (5) | C39—C41—H41 | 120.1 |
C6—C5—C4 | 120.0 | C41—C42—C43 | 119.4 (6) |
C6—C5—C10 | 120.0 | C41—C42—H42 | 120.3 |
C4—C5—C10 | 120.0 | C43—C42—H42 | 120.3 |
C7—C6—C5 | 120.0 | N4—C43—C42 | 122.4 (6) |
C7—C6—C1 | 120.0 | N4—C43—H43 | 118.8 |
C5—C6—C1 | 120.0 | C42—C43—H43 | 118.8 |
C6—C7—C8 | 120.0 | N5—C44—C45 | 121.8 (7) |
C6—C7—H7 | 120.0 | N5—C44—H44 | 119.1 |
C8—C7—H7 | 120.0 | C45—C44—H44 | 119.1 |
C9—C8—C7 | 120.0 | C46—C45—C44 | 121.2 (8) |
C9—C8—H8 | 120.0 | C46—C45—H45 | 119.4 |
C7—C8—H8 | 120.0 | C44—C45—H45 | 119.4 |
C8—C9—C10 | 120.0 | C45—C46—C47 | 118.1 (8) |
C8—C9—H9 | 120.0 | C45—C46—H46 | 120.9 |
C10—C9—H9 | 120.0 | C47—C46—H46 | 120.9 |
C9—C10—C5 | 120.0 | C48—C47—C46 | 118.1 (7) |
C9—C10—H10 | 120.0 | C48—C47—C49 | 118.2 (6) |
C5—C10—H10 | 120.0 | C46—C47—C49 | 123.7 (7) |
C2'—C1'—C6' | 120.0 | N5—C48—C47 | 122.1 (6) |
C2'—C1'—C11 | 119.4 (5) | N5—C48—C59 | 117.4 (6) |
C6'—C1'—C11 | 120.6 (5) | C47—C48—C59 | 120.4 (6) |
C1'—C2'—C3' | 120.0 | N6—C49—C57 | 111.1 (6) |
C1'—C2'—H2' | 120.0 | N6—C49—C47 | 129.0 (7) |
C3'—C2'—H2' | 120.0 | C57—C49—C47 | 119.9 (6) |
C2'—C3'—C4' | 120.0 | N6—C50—N7 | 111.9 (6) |
C2'—C3'—H3' | 120.0 | N6—C50—C51 | 124.6 (7) |
C4'—C3'—H3' | 120.0 | N7—C50—C51 | 123.3 (6) |
C5'—C4'—C3' | 120.0 | C52—C51—C56 | 119.3 (7) |
C5'—C4'—C12 | 122.6 (4) | C52—C51—C50 | 119.0 (7) |
C3'—C4'—C12 | 117.4 (4) | C56—C51—C50 | 121.7 (7) |
C4'—C5'—C6' | 120.0 | C51—C52—C53 | 119.8 (8) |
C4'—C5'—C10' | 120.0 | C51—C52—H52 | 120.1 |
C6'—C5'—C10' | 120.0 | C53—C52—H52 | 120.1 |
C7'—C6'—C5' | 120.0 | C54—C53—C52 | 121.2 (9) |
C7'—C6'—C1' | 120.0 | C54—C53—H53 | 119.4 |
C5'—C6'—C1' | 120.0 | C52—C53—H53 | 119.4 |
C8'—C7'—C6' | 120.0 | C53—C54—C55 | 119.9 (8) |
C8'—C7'—H7' | 120.0 | C53—C54—H54 | 120.0 |
C6'—C7'—H7' | 120.0 | C55—C54—H54 | 120.0 |
C9'—C8'—C7' | 120.0 | C54—C55—C56 | 119.2 (8) |
C9'—C8'—H8' | 120.0 | C54—C55—H55 | 120.4 |
C7'—C8'—H8' | 120.0 | C56—C55—H55 | 120.4 |
C10'—C9'—C8' | 120.0 | C51—C56—C55 | 120.5 (9) |
C10'—C9'—H9' | 120.0 | C51—C56—H56 | 119.7 |
C8'—C9'—H9' | 120.0 | C55—C56—H56 | 119.7 |
C9'—C10'—C5' | 120.0 | N7—C57—C49 | 105.1 (6) |
C9'—C10'—H10' | 120.0 | N7—C57—C58 | 130.6 (7) |
C5'—C10'—H10' | 120.0 | C49—C57—C58 | 124.2 (6) |
O2—C11—O1 | 124.3 (6) | C60—C58—C59 | 117.5 (7) |
O2—C11—C1 | 117.2 (7) | C60—C58—C57 | 125.7 (6) |
O1—C11—C1 | 118.5 (7) | C59—C58—C57 | 116.8 (6) |
O2—C11—C1' | 114.9 (7) | N8—C59—C58 | 123.1 (6) |
O1—C11—C1' | 120.7 (7) | N8—C59—C48 | 116.4 (6) |
O4—C12—O3 | 125.5 (6) | C58—C59—C48 | 120.4 (6) |
O4—C12—C4' | 118.6 (7) | C61—C60—C58 | 119.6 (7) |
O3—C12—C4' | 115.8 (7) | C61—C60—H60 | 120.2 |
O4—C12—C4 | 115.2 (7) | C58—C60—H60 | 120.2 |
O3—C12—C4 | 119.2 (8) | C60—C61—C62 | 118.2 (7) |
O6—C13—O5 | 122.5 (6) | C60—C61—H61 | 120.9 |
O6—C13—C14 | 119.2 (6) | C62—C61—H61 | 120.9 |
O5—C13—C14 | 118.2 (6) | N8—C62—C61 | 123.5 (8) |
O6—C13—Mn1 | 55.5 (3) | N8—C62—H62 | 118.2 |
O5—C13—Mn1 | 67.1 (4) | C61—C62—H62 | 118.2 |
C14—C13—Mn1 | 174.6 (5) | C63—N9—C64 | 129.9 (11) |
C23—C14—C15 | 118.5 (6) | C63—N9—C65 | 109.3 (11) |
C23—C14—C13 | 117.7 (7) | C64—N9—C65 | 120.8 (10) |
C15—C14—C13 | 123.7 (7) | O9—C63—N9 | 118.8 (16) |
C14—C15—C16 | 122.5 (6) | O9—C63—H63 | 120.6 |
C14—C15—C20 | 119.6 (6) | N9—C63—H63 | 120.6 |
C16—C15—C20 | 117.9 (6) | N9—C64—H64A | 109.5 |
C17—C16—C15 | 120.9 (7) | N9—C64—H64B | 109.5 |
C17—C16—H16 | 119.6 | H64A—C64—H64B | 109.5 |
C15—C16—H16 | 119.6 | N9—C64—H64C | 109.5 |
C16—C17—C18 | 120.4 (8) | H64A—C64—H64C | 109.5 |
C16—C17—H17 | 119.8 | H64B—C64—H64C | 109.5 |
C18—C17—H17 | 119.8 | N9—C65—H65A | 109.5 |
C19—C18—C17 | 120.8 (8) | N9—C65—H65B | 109.5 |
C19—C18—H18 | 119.6 | H65A—C65—H65B | 109.5 |
C17—C18—H18 | 119.6 | N9—C65—H65C | 109.5 |
C18—C19—C20 | 121.3 (7) | H65A—C65—H65C | 109.5 |
C18—C19—H19 | 119.3 | H65B—C65—H65C | 109.5 |
O3iii—Mn2—O2—C11 | 31.4 (8) | C13—C14—C15—C16 | 1.2 (9) |
O7—Mn2—O2—C11 | 139.3 (8) | C23—C14—C15—C20 | −1.1 (9) |
N5—Mn2—O2—C11 | −73.0 (8) | C13—C14—C15—C20 | −177.6 (5) |
O8—Mn2—O2—C11 | −165.0 (8) | C14—C15—C16—C17 | −177.1 (7) |
C24—Mn2—O2—C11 | 167.4 (8) | C20—C15—C16—C17 | 1.6 (10) |
O4ii—Mn1—O5—C13 | 98.9 (4) | C15—C16—C17—C18 | 1.2 (12) |
O1i—Mn1—O5—C13 | 17.7 (6) | C16—C17—C18—C19 | −2.9 (13) |
O6—Mn1—O5—C13 | −1.9 (3) | C17—C18—C19—C20 | 1.6 (12) |
N1—Mn1—O5—C13 | −161.1 (3) | C18—C19—C20—C21 | −179.7 (7) |
N4—Mn1—O5—C13 | −87.7 (4) | C18—C19—C20—C15 | 1.2 (10) |
O4ii—Mn1—O6—C13 | −75.0 (4) | C14—C15—C20—C19 | 176.1 (6) |
O1i—Mn1—O6—C13 | −171.0 (4) | C16—C15—C20—C19 | −2.7 (9) |
N1—Mn1—O6—C13 | 45.1 (5) | C14—C15—C20—C21 | −3.1 (8) |
N4—Mn1—O6—C13 | 95.4 (4) | C16—C15—C20—C21 | 178.1 (6) |
O5—Mn1—O6—C13 | 2.0 (3) | C19—C20—C21—C22 | −174.9 (6) |
O2—Mn2—O7—C24 | 78.8 (4) | C15—C20—C21—C22 | 4.3 (9) |
O3iii—Mn2—O7—C24 | 174.7 (4) | C19—C20—C21—C24 | 5.1 (9) |
N5—Mn2—O7—C24 | −39.9 (5) | C15—C20—C21—C24 | −175.8 (5) |
N8—Mn2—O7—C24 | −93.6 (4) | C20—C21—C22—C23 | −1.1 (9) |
O8—Mn2—O7—C24 | 1.5 (4) | C24—C21—C22—C23 | 178.9 (6) |
O2—Mn2—O8—C24 | −102.9 (4) | C15—C14—C23—C22 | 4.4 (9) |
O3iii—Mn2—O8—C24 | −24.9 (8) | C13—C14—C23—C22 | −178.9 (6) |
O7—Mn2—O8—C24 | −1.5 (4) | C21—C22—C23—C14 | −3.4 (10) |
N5—Mn2—O8—C24 | 155.2 (4) | Mn2—O8—C24—O7 | 2.6 (6) |
N8—Mn2—O8—C24 | 81.7 (4) | Mn2—O8—C24—C21 | −179.3 (6) |
O4ii—Mn1—N1—C25 | −8.7 (6) | Mn2—O7—C24—O8 | −2.9 (7) |
O1i—Mn1—N1—C25 | 89.0 (6) | Mn2—O7—C24—C21 | 179.0 (5) |
O6—Mn1—N1—C25 | −127.2 (6) | C22—C21—C24—O8 | −146.0 (6) |
N4—Mn1—N1—C25 | 179.5 (6) | C20—C21—C24—O8 | 34.0 (9) |
O5—Mn1—N1—C25 | −91.4 (6) | C22—C21—C24—O7 | 32.2 (9) |
C13—Mn1—N1—C25 | −102.6 (6) | C20—C21—C24—O7 | −147.8 (6) |
O4ii—Mn1—N1—C29 | 173.2 (4) | C29—N1—C25—C26 | −2.0 (10) |
O1i—Mn1—N1—C29 | −89.1 (5) | Mn1—N1—C25—C26 | 179.9 (6) |
O6—Mn1—N1—C29 | 54.7 (6) | N1—C25—C26—C27 | 1.7 (12) |
N4—Mn1—N1—C29 | 1.4 (4) | C25—C26—C27—C28 | 0.0 (12) |
O5—Mn1—N1—C29 | 90.5 (5) | C26—C27—C28—C29 | −1.2 (11) |
C13—Mn1—N1—C29 | 79.3 (5) | C26—C27—C28—C30 | 179.8 (7) |
O1i—Mn1—N4—C43 | −77.6 (6) | C25—N1—C29—C28 | 0.7 (10) |
O6—Mn1—N4—C43 | 24.5 (5) | Mn1—N1—C29—C28 | 178.9 (5) |
N1—Mn1—N4—C43 | 180.0 (6) | C25—N1—C29—C40 | −179.1 (6) |
O5—Mn1—N4—C43 | 82.3 (5) | Mn1—N1—C29—C40 | −0.8 (7) |
C13—Mn1—N4—C43 | 53.1 (6) | C27—C28—C29—N1 | 0.9 (10) |
O1i—Mn1—N4—C40 | 100.5 (5) | C30—C28—C29—N1 | 180.0 (6) |
O6—Mn1—N4—C40 | −157.4 (5) | C27—C28—C29—C40 | −179.4 (6) |
N1—Mn1—N4—C40 | −1.9 (4) | C30—C28—C29—C40 | −0.3 (10) |
O5—Mn1—N4—C40 | −99.6 (5) | C31—N2—C30—C38 | −0.3 (8) |
C13—Mn1—N4—C40 | −128.8 (5) | C31—N2—C30—C28 | 179.8 (7) |
O2—Mn2—N5—C44 | 5.6 (7) | C29—C28—C30—C38 | 1.5 (10) |
O3iii—Mn2—N5—C44 | −91.5 (6) | C27—C28—C30—C38 | −179.5 (7) |
O7—Mn2—N5—C44 | 122.3 (6) | C29—C28—C30—N2 | −178.6 (7) |
N8—Mn2—N5—C44 | 179.2 (7) | C27—C28—C30—N2 | 0.4 (12) |
O8—Mn2—N5—C44 | 88.5 (6) | C30—N2—C31—N3 | 0.3 (8) |
C24—Mn2—N5—C44 | 101.7 (6) | C30—N2—C31—C32 | −176.1 (7) |
O2—Mn2—N5—C48 | −172.7 (5) | C38—N3—C31—N2 | −0.1 (8) |
O3iii—Mn2—N5—C48 | 90.2 (5) | C38—N3—C31—C32 | 176.3 (7) |
O7—Mn2—N5—C48 | −56.0 (6) | N2—C31—C32—C37 | 172.2 (7) |
N8—Mn2—N5—C48 | 0.9 (5) | N3—C31—C32—C37 | −3.8 (11) |
O8—Mn2—N5—C48 | −89.9 (5) | N2—C31—C32—C33 | −6.2 (11) |
C24—Mn2—N5—C48 | −76.7 (5) | N3—C31—C32—C33 | 177.8 (7) |
O3iii—Mn2—N8—C62 | 74.5 (6) | C37—C32—C33—C34 | −1.3 (11) |
O7—Mn2—N8—C62 | −32.8 (6) | C31—C32—C33—C34 | 177.2 (7) |
N5—Mn2—N8—C62 | 177.3 (7) | C32—C33—C34—C35 | 1.5 (13) |
O8—Mn2—N8—C62 | −89.5 (6) | C33—C34—C35—C36 | −0.3 (13) |
C24—Mn2—N8—C62 | −61.4 (6) | C34—C35—C36—C37 | −1.0 (12) |
O3iii—Mn2—N8—C59 | −100.8 (5) | C35—C36—C37—C32 | 1.2 (12) |
O7—Mn2—N8—C59 | 152.0 (5) | C33—C32—C37—C36 | −0.1 (11) |
N5—Mn2—N8—C59 | 2.0 (5) | C31—C32—C37—C36 | −178.5 (7) |
O8—Mn2—N8—C59 | 95.2 (5) | N2—C30—C38—N3 | 0.3 (8) |
C24—Mn2—N8—C59 | 123.4 (5) | C28—C30—C38—N3 | −179.8 (6) |
C6—C1—C2—C3 | 0.0 | N2—C30—C38—C39 | 179.0 (6) |
C11—C1—C2—C3 | −179.8 (9) | C28—C30—C38—C39 | −1.1 (11) |
C1—C2—C3—C4 | 0.0 | C31—N3—C38—C30 | −0.1 (7) |
C2—C3—C4—C5 | 0.0 | C31—N3—C38—C39 | −178.7 (7) |
C2—C3—C4—C12 | −173.3 (9) | C30—C38—C39—C40 | −0.7 (10) |
C3—C4—C5—C6 | 0.0 | N3—C38—C39—C40 | 177.7 (7) |
C12—C4—C5—C6 | 172.9 (10) | C30—C38—C39—C41 | −177.5 (7) |
C3—C4—C5—C10 | 180.0 | N3—C38—C39—C41 | 0.9 (12) |
C12—C4—C5—C10 | −7.1 (10) | C43—N4—C40—C39 | 1.2 (10) |
C4—C5—C6—C7 | 180.0 | Mn1—N4—C40—C39 | −177.0 (5) |
C10—C5—C6—C7 | 0.0 | C43—N4—C40—C29 | −179.6 (6) |
C4—C5—C6—C1 | 0.0 | Mn1—N4—C40—C29 | 2.2 (7) |
C10—C5—C6—C1 | 180.0 | C38—C39—C40—N4 | −178.9 (6) |
C2—C1—C6—C7 | 180.0 | C41—C39—C40—N4 | −1.8 (10) |
C11—C1—C6—C7 | −0.2 (9) | C38—C39—C40—C29 | 1.9 (9) |
C2—C1—C6—C5 | 0.0 | C41—C39—C40—C29 | 179.0 (6) |
C11—C1—C6—C5 | 179.8 (9) | N1—C29—C40—N4 | −1.0 (9) |
C5—C6—C7—C8 | 0.0 | C28—C29—C40—N4 | 179.3 (6) |
C1—C6—C7—C8 | 180.0 | N1—C29—C40—C39 | 178.2 (6) |
C6—C7—C8—C9 | 0.0 | C28—C29—C40—C39 | −1.5 (10) |
C7—C8—C9—C10 | 0.0 | C40—C39—C41—C42 | 2.1 (10) |
C8—C9—C10—C5 | 0.0 | C38—C39—C41—C42 | 178.9 (7) |
C6—C5—C10—C9 | 0.0 | C39—C41—C42—C43 | −1.9 (11) |
C4—C5—C10—C9 | 180.0 | C40—N4—C43—C42 | −0.9 (10) |
C6'—C1'—C2'—C3' | 0.0 | Mn1—N4—C43—C42 | 177.1 (5) |
C11—C1'—C2'—C3' | 176.5 (9) | C41—C42—C43—N4 | 1.3 (12) |
C1'—C2'—C3'—C4' | 0.0 | C48—N5—C44—C45 | 0.8 (12) |
C2'—C3'—C4'—C5' | 0.0 | Mn2—N5—C44—C45 | −177.5 (7) |
C2'—C3'—C4'—C12 | −177.1 (8) | N5—C44—C45—C46 | −2.2 (15) |
C3'—C4'—C5'—C6' | 0.0 | C44—C45—C46—C47 | 1.9 (15) |
C12—C4'—C5'—C6' | 176.9 (8) | C45—C46—C47—C48 | −0.5 (12) |
C3'—C4'—C5'—C10' | 180.0 | C45—C46—C47—C49 | −178.7 (8) |
C12—C4'—C5'—C10' | −3.1 (8) | C44—N5—C48—C47 | 0.7 (10) |
C4'—C5'—C6'—C7' | 180.0 | Mn2—N5—C48—C47 | 179.1 (5) |
C10'—C5'—C6'—C7' | 0.0 | C44—N5—C48—C59 | 178.1 (6) |
C4'—C5'—C6'—C1' | 0.0 | Mn2—N5—C48—C59 | −3.4 (7) |
C10'—C5'—C6'—C1' | 180.0 | C46—C47—C48—N5 | −0.8 (11) |
C2'—C1'—C6'—C7' | 180.0 | C49—C47—C48—N5 | 177.5 (6) |
C11—C1'—C6'—C7' | 3.6 (9) | C46—C47—C48—C59 | −178.2 (7) |
C2'—C1'—C6'—C5' | 0.0 | C49—C47—C48—C59 | 0.1 (10) |
C11—C1'—C6'—C5' | −176.4 (9) | C50—N6—C49—C57 | −0.9 (8) |
C5'—C6'—C7'—C8' | 0.0 | C50—N6—C49—C47 | −178.9 (7) |
C1'—C6'—C7'—C8' | 180.0 | C48—C47—C49—N6 | 175.6 (7) |
C6'—C7'—C8'—C9' | 0.0 | C46—C47—C49—N6 | −6.2 (13) |
C7'—C8'—C9'—C10' | 0.0 | C48—C47—C49—C57 | −2.2 (10) |
C8'—C9'—C10'—C5' | 0.0 | C46—C47—C49—C57 | 176.0 (7) |
C4'—C5'—C10'—C9' | 180.0 | C49—N6—C50—N7 | 0.9 (8) |
C6'—C5'—C10'—C9' | 0.0 | C49—N6—C50—C51 | 176.8 (7) |
Mn2—O2—C11—O1 | 25.4 (13) | C57—N7—C50—N6 | −0.6 (8) |
Mn2—O2—C11—C1 | −153.6 (6) | C57—N7—C50—C51 | −176.5 (7) |
Mn2—O2—C11—C1' | −158.4 (6) | N6—C50—C51—C52 | 5.0 (12) |
Mn1v—O1—C11—O2 | −116.3 (8) | N7—C50—C51—C52 | −179.6 (7) |
Mn1v—O1—C11—C1 | 62.7 (9) | N6—C50—C51—C56 | −172.3 (7) |
Mn1v—O1—C11—C1' | 67.7 (9) | N7—C50—C51—C56 | 3.1 (12) |
C2—C1—C11—O2 | −128.5 (7) | C56—C51—C52—C53 | 1.0 (14) |
C6—C1—C11—O2 | 51.7 (11) | C50—C51—C52—C53 | −176.3 (8) |
C2—C1—C11—O1 | 52.5 (9) | C51—C52—C53—C54 | −2.7 (16) |
C6—C1—C11—O1 | −127.3 (7) | C52—C53—C54—C55 | 1.8 (17) |
C2—C1—C11—C1' | −66 (7) | C53—C54—C55—C56 | 0.7 (16) |
C6—C1—C11—C1' | 114 (7) | C52—C51—C56—C55 | 1.5 (13) |
C2'—C1'—C11—O2 | 59.2 (9) | C50—C51—C56—C55 | 178.7 (8) |
C6'—C1'—C11—O2 | −124.4 (8) | C54—C55—C56—C51 | −2.4 (14) |
C2'—C1'—C11—O1 | −124.4 (7) | C50—N7—C57—C49 | 0.0 (7) |
C6'—C1'—C11—O1 | 52.0 (11) | C50—N7—C57—C58 | 176.6 (7) |
C2'—C1'—C11—C1 | −60 (7) | N6—C49—C57—N7 | 0.6 (8) |
C6'—C1'—C11—C1 | 116 (7) | C47—C49—C57—N7 | 178.8 (6) |
Mn1iv—O4—C12—O3 | −27.7 (11) | N6—C49—C57—C58 | −176.3 (7) |
Mn1iv—O4—C12—C4' | 148.4 (6) | C47—C49—C57—C58 | 1.9 (11) |
Mn1iv—O4—C12—C4 | 156.8 (6) | N7—C57—C58—C60 | 2.2 (13) |
Mn2vi—O3—C12—O4 | 114.4 (8) | C49—C57—C58—C60 | 178.2 (7) |
Mn2vi—O3—C12—C4' | −61.8 (8) | N7—C57—C58—C59 | −175.3 (7) |
Mn2vi—O3—C12—C4 | −70.3 (9) | C49—C57—C58—C59 | 0.7 (11) |
C5'—C4'—C12—O4 | −53.8 (10) | C62—N8—C59—C58 | 0.3 (10) |
C3'—C4'—C12—O4 | 123.1 (6) | Mn2—N8—C59—C58 | 175.9 (5) |
C5'—C4'—C12—O3 | 122.6 (7) | C62—N8—C59—C48 | 180.0 (6) |
C3'—C4'—C12—O3 | −60.4 (7) | Mn2—N8—C59—C48 | −4.4 (8) |
C5'—C4'—C12—C4 | −121 (5) | C60—C58—C59—N8 | −0.9 (11) |
C3'—C4'—C12—C4 | 56 (4) | C57—C58—C59—N8 | 176.9 (6) |
C3—C4—C12—O4 | −58.9 (8) | C60—C58—C59—C48 | 179.5 (7) |
C5—C4—C12—O4 | 128.0 (7) | C57—C58—C59—C48 | −2.8 (10) |
C3—C4—C12—O3 | 125.4 (6) | N5—C48—C59—N8 | 5.3 (9) |
C5—C4—C12—O3 | −47.7 (11) | C47—C48—C59—N8 | −177.2 (6) |
C3—C4—C12—C4' | 58 (4) | N5—C48—C59—C58 | −175.0 (6) |
C5—C4—C12—C4' | −116 (5) | C47—C48—C59—C58 | 2.4 (10) |
Mn1—O6—C13—O5 | −3.8 (7) | C59—C58—C60—C61 | 1.3 (12) |
Mn1—O6—C13—C14 | 179.5 (5) | C57—C58—C60—C61 | −176.2 (8) |
Mn1—O5—C13—O6 | 3.4 (6) | C58—C60—C61—C62 | −1.2 (13) |
Mn1—O5—C13—C14 | −179.9 (5) | C59—N8—C62—C61 | −0.2 (12) |
O6—C13—C14—C23 | 151.0 (6) | Mn2—N8—C62—C61 | −175.3 (6) |
O5—C13—C14—C23 | −25.9 (8) | C60—C61—C62—N8 | 0.6 (13) |
O6—C13—C14—C15 | −32.5 (9) | C64—N9—C63—O9 | −0.3 (4) |
O5—C13—C14—C15 | 150.6 (6) | C65—N9—C63—O9 | −179.8 (13) |
C23—C14—C15—C16 | 177.6 (6) |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) x+1, y, z; (iv) x−1, y−1, z; (v) x, y−1, z; (vi) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Mn2(C12H6O4)2(C19H12N4)2]·C3H7NO |
Mr | 1203.96 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 9.240 (2), 14.852 (5), 21.921 (5) |
α, β, γ (°) | 105.72 (1), 100.48 (1), 101.67 (1) |
V (Å3) | 2745.0 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.53 |
Crystal size (mm) | 0.26 × 0.16 × 0.12 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.760, 0.940 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21501, 9443, 4800 |
Rint | 0.084 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.080, 0.262, 1.06 |
No. of reflections | 9443 |
No. of parameters | 810 |
No. of restraints | 158 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.74, −0.48 |
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—O1i | 2.115 (5) | Mn2—O2 | 2.107 (5) |
Mn1—O4ii | 2.105 (4) | Mn2—O3iii | 2.112 (5) |
Mn1—O5 | 2.431 (5) | Mn2—O7 | 2.208 (5) |
Mn1—O6 | 2.171 (5) | Mn2—O8 | 2.384 (5) |
Mn1—N1 | 2.232 (5) | Mn2—N5 | 2.252 (6) |
Mn1—N4 | 2.259 (5) | Mn2—N8 | 2.277 (5) |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) x+1, y, z. |
Acknowledgements
We thank the Natural Science Foundation of Jilin Province (No. 20060516), the Doctoral Foundation of Jilin Normal University (No. 2006006), the Science and Technology Institute Foundation of Siping City (No. 2005016), the Subject and Base Construction Foundation of Jilin Normal University (No. 2006041), and the University of Malaya for supporting this work.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
There are several studies of metal complexes of 2-phenyl-1H-1,3,7,8-tetraazacyclopenta[l]phenanthrene. Among these are several manganese complexes, the manganese succinate (Zhang et al., 2006), manganese adipate (Wang et al., 2006), manganese isophthalate (Che & Liu, 2006) and manganese terephthalate (Che, 2006) adducts, all of which feature carboxylate-bridged chain motifs. The title naphthalene-1,4-dicarboxylate adduct adopts a layer motif instead.
One of the two 1,4-dicarboxylate dianions in Mn2(C19H12N4)2(C12H6O4)2.DMF uses its two carboxyl –CO2 groups to chelate to two N-heterocycle-chelated manganese atoms; the other 1,4-dicarboxylate dianion binds to four such metal centers. The octahedrally coordinated manganese atoms are linked through the two dianions into a layer motif; the DMF molecules occupy the spaces between adjacent layers.