In the title compound, [Mn(C
8H
4O
4)(C
19H
12N
4)
2], the Mn
II atom (site symmetry
) is six-coordinated by two bidentate phenanthrene and two monodentate benzene-1,4-dicarboxylate ligands, resulting in a distorted
trans-MnO
2N
4 octahedral coordination geometry. The Mn
II atoms are bridged by the centrosymmetric benzene-1,4-dicarboxylate ligands to form an extended single-chain structure. In addition, neighbouring single chains interact through π–π interactions, generating a two-dimensional network.
Supporting information
CCDC reference: 610785
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.005 Å
- R factor = 0.054
- wR factor = 0.142
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.01
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.35
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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
checkCIF publication errors
Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 107
In the title compound, [Mn(C~8~H~4~O~4)(C~19~H~12~N~4~)~2~],
If you require a ~ then it should be escaped
with a \, i.e. \~
Otherwise there must be a matching closing ~, e.g. C~2~H~4~
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXTL-Plus.
catena-Poly[[(2-phenyl-1
H-1,3,7,8-
tetraazacyclopenta[
l]phenanthrene)manganese(II)]-µ-benzene-1,4-dicarboxylato]
top
Crystal data top
[Mn(C8H4O4)(C19H12N4)2] | Z = 1 |
Mr = 811.72 | F(000) = 417 |
Triclinic, P1 | Dx = 1.519 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6550 (19) Å | Cell parameters from 6215 reflections |
b = 10.451 (2) Å | θ = 3.3–27.5° |
c = 10.626 (2) Å | µ = 0.43 mm−1 |
α = 90.48 (3)° | T = 292 K |
β = 114.87 (3)° | Block, yellow |
γ = 111.63 (3)° | 0.30 × 0.27 × 0.17 mm |
V = 887.1 (5) Å3 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 4009 independent reflections |
Radiation source: rotor target | 2443 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.5°, θmin = 3.3° |
ω scans | h = −11→12 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −13→13 |
Tmin = 0.872, Tmax = 0.918 | l = −13→13 |
8728 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0625P)2 + 0.1905P] where P = (Fo2 + 2Fc2)/3 |
4009 reflections | (Δ/σ)max < 0.001 |
268 parameters | Δρmax = 0.89 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C8 | −0.3568 (5) | −0.1731 (4) | −0.4734 (4) | 0.0541 (9) | |
H8 | −0.4334 | −0.1479 | −0.5447 | 0.065* | |
C9 | −0.2493 (5) | −0.0841 (3) | −0.3413 (4) | 0.0481 (8) | |
H9 | −0.2540 | 0.0020 | −0.3282 | 0.058* | |
C10 | −0.1286 (4) | −0.2367 (3) | −0.2561 (3) | 0.0347 (7) | |
N2 | −0.1421 (3) | −0.1148 (3) | −0.2344 (3) | 0.0395 (6) | |
C1 | 0.2105 (4) | −0.1937 (4) | 0.0864 (4) | 0.0495 (9) | |
H1 | 0.2734 | −0.1289 | 0.1712 | 0.059* | |
C2 | 0.2484 (5) | −0.3083 (4) | 0.0768 (4) | 0.0563 (10) | |
H2 | 0.3357 | −0.3186 | 0.1524 | 0.068* | |
C3 | 0.1549 (4) | −0.4051 (3) | −0.0457 (4) | 0.0496 (9) | |
H3 | 0.1756 | −0.4841 | −0.0541 | 0.059* | |
C4 | 0.0281 (4) | −0.3852 (3) | −0.1585 (3) | 0.0392 (7) | |
C5 | −0.0009 (4) | −0.2653 (3) | −0.1410 (3) | 0.0349 (7) | |
C6 | −0.2286 (4) | −0.3307 (3) | −0.3872 (3) | 0.0389 (7) | |
C7 | −0.3470 (5) | −0.2980 (4) | −0.4957 (4) | 0.0482 (8) | |
H7 | −0.4184 | −0.3601 | −0.5819 | 0.058* | |
C11 | −0.1968 (4) | −0.4519 (3) | −0.4028 (3) | 0.0398 (7) | |
C12 | −0.0752 (4) | −0.4765 (3) | −0.2935 (3) | 0.0395 (7) | |
C13 | −0.1945 (4) | −0.6379 (3) | −0.4845 (3) | 0.0390 (7) | |
C14 | −0.2296 (4) | −0.7600 (3) | −0.5808 (3) | 0.0375 (7) | |
C15 | −0.3702 (5) | −0.8043 (4) | −0.7108 (4) | 0.0517 (9) | |
H15 | −0.4425 | −0.7596 | −0.7333 | 0.062* | |
C16 | −0.4042 (5) | −0.9148 (4) | −0.8079 (4) | 0.0561 (10) | |
H16 | −0.4980 | −0.9426 | −0.8956 | 0.067* | |
C17 | −0.3002 (5) | −0.9832 (4) | −0.7752 (4) | 0.0511 (9) | |
H17 | −0.3232 | −1.0572 | −0.8405 | 0.061* | |
C18 | −0.1620 (5) | −0.9417 (4) | −0.6457 (4) | 0.0506 (9) | |
H18 | −0.0922 | −0.9888 | −0.6231 | 0.061* | |
C19 | −0.1251 (4) | −0.8300 (3) | −0.5475 (4) | 0.0442 (8) | |
H19 | −0.0309 | −0.8024 | −0.4601 | 0.053* | |
C20 | 0.1984 (4) | 0.2453 (3) | −0.0889 (3) | 0.0350 (7) | |
C21 | 0.3566 (4) | 0.3766 (3) | −0.0435 (3) | 0.0328 (6) | |
C22 | 0.4636 (4) | 0.4312 (3) | 0.0998 (3) | 0.0376 (7) | |
H22 | 0.4385 | 0.3853 | 0.1670 | 0.045* | |
C23 | 0.6068 (4) | 0.5533 (3) | 0.1426 (3) | 0.0377 (7) | |
H23 | 0.6789 | 0.5883 | 0.2384 | 0.045* | |
N1 | 0.0912 (3) | −0.1710 (3) | −0.0169 (3) | 0.0394 (6) | |
N3 | −0.0743 (3) | −0.5966 (3) | −0.3466 (3) | 0.0420 (7) | |
H3A | −0.0107 | −0.6376 | −0.3018 | 0.050* | |
N4 | −0.2722 (3) | −0.5535 (3) | −0.5228 (3) | 0.0422 (6) | |
O1 | 0.2068 (3) | 0.1568 (2) | −0.0092 (2) | 0.0412 (5) | |
O2 | 0.0715 (3) | 0.2330 (2) | −0.1983 (2) | 0.0475 (6) | |
Mn1 | 0.0000 | 0.0000 | 0.0000 | 0.0343 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C8 | 0.068 (2) | 0.055 (2) | 0.046 (2) | 0.037 (2) | 0.0209 (19) | 0.0118 (17) |
C9 | 0.067 (2) | 0.0395 (18) | 0.047 (2) | 0.0306 (18) | 0.0273 (19) | 0.0101 (15) |
C10 | 0.0412 (17) | 0.0272 (14) | 0.0406 (18) | 0.0132 (14) | 0.0235 (15) | 0.0049 (12) |
N2 | 0.0527 (16) | 0.0309 (13) | 0.0437 (16) | 0.0208 (13) | 0.0266 (14) | 0.0082 (11) |
C1 | 0.047 (2) | 0.0471 (19) | 0.044 (2) | 0.0199 (17) | 0.0117 (17) | −0.0083 (15) |
C2 | 0.056 (2) | 0.058 (2) | 0.050 (2) | 0.033 (2) | 0.0105 (18) | −0.0045 (17) |
C3 | 0.056 (2) | 0.0408 (18) | 0.050 (2) | 0.0258 (17) | 0.0168 (18) | −0.0004 (15) |
C4 | 0.0463 (18) | 0.0284 (14) | 0.0423 (19) | 0.0139 (14) | 0.0209 (15) | 0.0029 (13) |
C5 | 0.0382 (16) | 0.0244 (14) | 0.0403 (18) | 0.0082 (13) | 0.0205 (14) | 0.0020 (12) |
C6 | 0.0453 (18) | 0.0335 (16) | 0.0370 (18) | 0.0152 (15) | 0.0188 (15) | 0.0055 (13) |
C7 | 0.059 (2) | 0.0449 (19) | 0.0398 (19) | 0.0254 (18) | 0.0183 (17) | 0.0036 (15) |
C11 | 0.0497 (19) | 0.0296 (15) | 0.0397 (18) | 0.0153 (15) | 0.0207 (16) | 0.0031 (13) |
C12 | 0.0511 (19) | 0.0269 (14) | 0.0399 (18) | 0.0146 (14) | 0.0215 (16) | 0.0040 (13) |
C13 | 0.0481 (19) | 0.0288 (15) | 0.0361 (18) | 0.0139 (14) | 0.0172 (15) | 0.0014 (13) |
C14 | 0.0458 (18) | 0.0315 (15) | 0.0393 (18) | 0.0157 (14) | 0.0231 (16) | 0.0047 (13) |
C15 | 0.056 (2) | 0.050 (2) | 0.049 (2) | 0.0273 (18) | 0.0187 (19) | 0.0005 (16) |
C16 | 0.060 (2) | 0.057 (2) | 0.040 (2) | 0.020 (2) | 0.0161 (18) | −0.0065 (17) |
C17 | 0.063 (2) | 0.0443 (19) | 0.046 (2) | 0.0222 (18) | 0.0253 (19) | −0.0057 (16) |
C18 | 0.065 (2) | 0.047 (2) | 0.055 (2) | 0.0318 (19) | 0.033 (2) | 0.0092 (16) |
C19 | 0.0491 (19) | 0.0401 (18) | 0.0413 (19) | 0.0164 (16) | 0.0205 (16) | 0.0024 (14) |
C20 | 0.0389 (17) | 0.0262 (14) | 0.0409 (18) | 0.0115 (13) | 0.0204 (15) | 0.0044 (13) |
C21 | 0.0364 (16) | 0.0248 (13) | 0.0396 (18) | 0.0122 (13) | 0.0199 (15) | 0.0064 (12) |
C22 | 0.0442 (18) | 0.0329 (15) | 0.0382 (18) | 0.0134 (14) | 0.0230 (15) | 0.0121 (13) |
C23 | 0.0430 (18) | 0.0335 (15) | 0.0315 (17) | 0.0121 (14) | 0.0156 (15) | 0.0036 (13) |
N1 | 0.0382 (14) | 0.0326 (13) | 0.0391 (15) | 0.0099 (12) | 0.0144 (13) | −0.0025 (11) |
N3 | 0.0544 (17) | 0.0305 (13) | 0.0422 (17) | 0.0212 (13) | 0.0198 (14) | 0.0029 (11) |
N4 | 0.0524 (17) | 0.0338 (14) | 0.0386 (15) | 0.0180 (13) | 0.0189 (13) | 0.0026 (11) |
O1 | 0.0410 (12) | 0.0269 (10) | 0.0541 (14) | 0.0094 (10) | 0.0240 (11) | 0.0114 (10) |
O2 | 0.0400 (13) | 0.0369 (12) | 0.0463 (14) | 0.0083 (10) | 0.0090 (12) | 0.0056 (10) |
Mn1 | 0.0399 (4) | 0.0208 (3) | 0.0418 (4) | 0.0090 (3) | 0.0213 (3) | 0.0028 (3) |
Geometric parameters (Å, º) top
C8—C7 | 1.369 (4) | C14—C15 | 1.384 (5) |
C8—C9 | 1.398 (5) | C14—C19 | 1.388 (4) |
C8—H8 | 0.9300 | C15—C16 | 1.385 (5) |
C9—N2 | 1.313 (4) | C15—H15 | 0.9300 |
C9—H9 | 0.9300 | C16—C17 | 1.371 (5) |
C10—N2 | 1.355 (3) | C16—H16 | 0.9300 |
C10—C6 | 1.409 (4) | C17—C18 | 1.372 (5) |
C10—C5 | 1.455 (4) | C17—H17 | 0.9300 |
C1—N1 | 1.315 (4) | C18—C19 | 1.392 (4) |
C1—C2 | 1.391 (4) | C18—H18 | 0.9300 |
C1—H1 | 0.9300 | C19—H19 | 0.9300 |
C2—C3 | 1.360 (5) | C20—C21 | 1.508 (4) |
C2—H2 | 0.9300 | C21—C23i | 1.380 (4) |
C3—C4 | 1.391 (5) | C21—C22 | 1.393 (4) |
C3—H3 | 0.9300 | C22—C23 | 1.381 (4) |
C4—C5 | 1.408 (4) | C22—H22 | 0.9300 |
C4—C12 | 1.427 (4) | C23—C21i | 1.380 (4) |
C5—N1 | 1.359 (4) | C23—H23 | 0.9300 |
C6—C7 | 1.392 (5) | N3—H3A | 0.8600 |
C6—C11 | 1.433 (4) | Mn1—O1 | 2.106 (2) |
C7—H7 | 0.9300 | Mn1—O1ii | 2.106 (2) |
C11—C12 | 1.369 (4) | Mn1—N1 | 2.300 (2) |
C11—N4 | 1.381 (4) | Mn1—N2 | 2.321 (3) |
C12—N3 | 1.376 (3) | Mn1—N1ii | 2.300 (2) |
C13—N4 | 1.321 (4) | Mn1—N2ii | 2.321 (3) |
C13—N3 | 1.367 (4) | C20—O2 | 1.246 (4) |
C13—C14 | 1.468 (4) | C20—O1 | 1.261 (4) |
| | | |
C7—C8—C9 | 118.6 (3) | C17—C16—C15 | 120.3 (3) |
C7—C8—H8 | 120.7 | C17—C16—H16 | 119.8 |
C9—C8—H8 | 120.7 | C15—C16—H16 | 119.8 |
N2—C9—C8 | 124.0 (3) | C16—C17—C18 | 119.6 (3) |
N2—C9—H9 | 118.0 | C16—C17—H17 | 120.2 |
C8—C9—H9 | 118.0 | C18—C17—H17 | 120.2 |
N2—C10—C6 | 121.8 (3) | C17—C18—C19 | 120.8 (3) |
N2—C10—C5 | 117.8 (3) | C17—C18—H18 | 119.6 |
C6—C10—C5 | 120.3 (2) | C19—C18—H18 | 119.6 |
C9—N2—C10 | 117.9 (3) | C14—C19—C18 | 119.7 (3) |
C9—N2—Mn1 | 126.8 (2) | C14—C19—H19 | 120.2 |
C10—N2—Mn1 | 114.6 (2) | C18—C19—H19 | 120.2 |
N1—C1—C2 | 124.1 (3) | O2—C20—O1 | 125.4 (3) |
N1—C1—H1 | 117.9 | O2—C20—C21 | 118.9 (3) |
C2—C1—H1 | 117.9 | O1—C20—C21 | 115.7 (3) |
C3—C2—C1 | 118.4 (3) | C23i—C21—C22 | 119.5 (3) |
C3—C2—H2 | 120.8 | C23i—C21—C20 | 120.6 (3) |
C1—C2—H2 | 120.8 | C22—C21—C20 | 119.8 (3) |
C2—C3—C4 | 119.6 (3) | C23—C22—C21 | 120.3 (3) |
C2—C3—H3 | 120.2 | C23—C22—H22 | 119.8 |
C4—C3—H3 | 120.2 | C21—C22—H22 | 119.8 |
C3—C4—C5 | 118.5 (3) | C21i—C23—C22 | 120.2 (3) |
C3—C4—C12 | 125.0 (3) | C21i—C23—H23 | 119.9 |
C5—C4—C12 | 116.5 (3) | C22—C23—H23 | 119.9 |
N1—C5—C4 | 121.3 (3) | C1—N1—C5 | 118.1 (3) |
N1—C5—C10 | 117.6 (2) | C1—N1—Mn1 | 125.9 (2) |
C4—C5—C10 | 121.1 (3) | C5—N1—Mn1 | 115.6 (2) |
C7—C6—C10 | 118.6 (3) | C13—N3—C12 | 106.6 (3) |
C7—C6—C11 | 123.7 (3) | C13—N3—H3A | 126.7 |
C10—C6—C11 | 117.6 (3) | C12—N3—H3A | 126.7 |
C8—C7—C6 | 119.0 (3) | C13—N4—C11 | 104.3 (3) |
C8—C7—H7 | 120.5 | C20—O1—Mn1 | 125.0 (2) |
C6—C7—H7 | 120.5 | O1—Mn1—O1ii | 180.0 |
C12—C11—N4 | 111.1 (3) | O1—Mn1—N1ii | 87.85 (9) |
C12—C11—C6 | 121.1 (3) | O1ii—Mn1—N1ii | 92.15 (9) |
N4—C11—C6 | 127.7 (3) | O1—Mn1—N1 | 92.15 (9) |
C11—C12—N3 | 105.6 (3) | O1ii—Mn1—N1 | 87.85 (9) |
C11—C12—C4 | 123.3 (3) | N1ii—Mn1—N1 | 180.0 |
N3—C12—C4 | 131.0 (3) | O1—Mn1—N2ii | 81.99 (10) |
N4—C13—N3 | 112.5 (2) | O1ii—Mn1—N2ii | 98.01 (10) |
N4—C13—C14 | 123.7 (3) | N1ii—Mn1—N2ii | 72.02 (9) |
N3—C13—C14 | 123.8 (3) | N1—Mn1—N2ii | 107.98 (9) |
C15—C14—C19 | 119.0 (3) | O1—Mn1—N2 | 98.01 (10) |
C15—C14—C13 | 118.5 (3) | O1ii—Mn1—N2 | 81.99 (10) |
C19—C14—C13 | 122.5 (3) | N1ii—Mn1—N2 | 107.98 (9) |
C14—C15—C16 | 120.6 (3) | N1—Mn1—N2 | 72.02 (9) |
C14—C15—H15 | 119.7 | N2ii—Mn1—N2 | 180.0 |
C16—C15—H15 | 119.7 | | |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O2iii | 0.86 | 1.94 | 2.769 (4) | 163 |
Symmetry code: (iii) x, y−1, z. |