In the title compound, {[Mn(endc)(phen)(H2O)]·H2O}n [phen is 1,10-phenanthroline (C12H8N2) and endc is the endo-norbornene-cis-5,6-dicarboxylate anion (C9H8O4)], each MnII ion is surrounded by two N atoms from a phen ligand, four O atoms from water molecules and two carboxylate groups of two endc anions, with one endc carboxylate group coordinating in a monodentate fashion and the other in a chelating fashion, forming a distorted MnO4N2 octahedron. The endc anions act as bridges between MnII ions, resulting in a zigzag chain structure along the [010] axis.
Supporting information
CCDC reference: 274330
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.040
- wR factor = 0.099
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor O6 - H6B ... ?
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
0 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.
catena-Poly[[[aqua(1,10-phenanthroline)manganese(II)]-µ-
endo-norbornene-
cis-5,6-dicarboxylato] monohydrate]
top
Crystal data top
[Mn(C9H8O4)(C12H8N2)(H2O)]·H2O | F(000) = 932 |
Mr = 451.33 | Dx = 1.542 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4067 reflections |
a = 10.941 (3) Å | θ = 2.5–24.9° |
b = 9.135 (2) Å | µ = 0.72 mm−1 |
c = 20.013 (4) Å | T = 298 K |
β = 103.605 (4)° | Block, pink |
V = 1944.1 (8) Å3 | 0.27 × 0.23 × 0.21 mm |
Z = 4 | |
Data collection top
Bruker APEX CCD area-detector diffractometer | 3501 independent reflections |
Radiation source: fine-focus sealed tube | 3002 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 25.3°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −13→9 |
Tmin = 0.829, Tmax = 0.863 | k = −9→10 |
9928 measured reflections | l = −24→23 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0491P)2 + 0.9627P] where P = (Fo2 + 2Fc2)/3 |
3501 reflections | (Δ/σ)max < 0.001 |
271 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.25 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 | |
Mn1 | 0.54328 (3) | 0.25324 (4) | 0.173606 (17) | 0.03121 (13) | |
O1 | 0.67961 (15) | 0.41325 (17) | 0.21165 (8) | 0.0351 (4) | |
O2 | 0.79614 (16) | 0.32338 (18) | 0.30950 (9) | 0.0427 (4) | |
O3 | 0.60661 (16) | 0.83219 (17) | 0.27767 (8) | 0.0368 (4) | |
O4 | 0.63046 (15) | 0.61386 (16) | 0.32313 (8) | 0.0361 (4) | |
O5 | 0.65970 (19) | 0.10364 (19) | 0.24268 (9) | 0.0565 (5) | |
H5A | 0.7103 | 0.1486 | 0.2723 | 0.068* | |
H5B | 0.6354 | 0.0255 | 0.2551 | 0.068* | |
O6 | 0.9932 (5) | 0.1852 (5) | 0.4001 (3) | 0.236 (3) | |
H6A | 0.9576 | 0.2213 | 0.3631 | 0.283* | |
H6B | 0.9565 | 0.1962 | 0.4310 | 0.283* | |
N1 | 0.42814 (18) | 0.3548 (2) | 0.07296 (9) | 0.0336 (4) | |
N2 | 0.60989 (18) | 0.1488 (2) | 0.08592 (9) | 0.0326 (4) | |
C1 | 0.9014 (3) | 0.7807 (3) | 0.33231 (16) | 0.0486 (7) | |
H1 | 0.8990 | 0.8878 | 0.3344 | 0.058* | |
C2 | 0.9013 (3) | 0.7027 (3) | 0.39818 (15) | 0.0520 (7) | |
H2 | 0.8748 | 0.7410 | 0.4355 | 0.062* | |
C3 | 0.9453 (2) | 0.5704 (3) | 0.39358 (14) | 0.0482 (7) | |
H3 | 0.9544 | 0.4978 | 0.4269 | 0.058* | |
C4 | 0.9785 (2) | 0.5565 (3) | 0.32502 (13) | 0.0426 (6) | |
H4 | 1.0399 | 0.4802 | 0.3219 | 0.051* | |
C5 | 0.8544 (2) | 0.5534 (2) | 0.26790 (12) | 0.0338 (5) | |
H5 | 0.8801 | 0.5547 | 0.2242 | 0.041* | |
C6 | 0.7968 (2) | 0.7077 (2) | 0.27458 (12) | 0.0347 (5) | |
H6 | 0.7913 | 0.7613 | 0.2315 | 0.042* | |
C7 | 1.0201 (3) | 0.7149 (3) | 0.31557 (17) | 0.0540 (7) | |
H7A | 1.0969 | 0.7423 | 0.3484 | 0.065* | |
H7B | 1.0270 | 0.7357 | 0.2691 | 0.065* | |
C8 | 0.7699 (2) | 0.4200 (2) | 0.26468 (11) | 0.0311 (5) | |
C9 | 0.6701 (2) | 0.7148 (2) | 0.29258 (11) | 0.0288 (5) | |
C10 | 0.3362 (2) | 0.4516 (3) | 0.06601 (13) | 0.0414 (6) | |
H10 | 0.3148 | 0.4857 | 0.1055 | 0.050* | |
C11 | 0.2696 (3) | 0.5054 (3) | 0.00287 (14) | 0.0467 (6) | |
H11 | 0.2044 | 0.5719 | 0.0006 | 0.056* | |
C12 | 0.3014 (3) | 0.4594 (3) | −0.05549 (13) | 0.0465 (7) | |
H12 | 0.2591 | 0.4957 | −0.0981 | 0.056* | |
C13 | 0.3983 (2) | 0.3567 (3) | −0.05095 (12) | 0.0391 (6) | |
C14 | 0.4386 (3) | 0.3027 (3) | −0.10956 (13) | 0.0492 (7) | |
H14 | 0.4007 | 0.3384 | −0.1530 | 0.059* | |
C15 | 0.5299 (3) | 0.2018 (3) | −0.10306 (13) | 0.0473 (7) | |
H15 | 0.5539 | 0.1684 | −0.1420 | 0.057* | |
C16 | 0.5906 (2) | 0.1450 (3) | −0.03712 (12) | 0.0383 (6) | |
C17 | 0.6855 (2) | 0.0385 (3) | −0.02794 (14) | 0.0457 (6) | |
H17 | 0.7119 | 0.0019 | −0.0656 | 0.055* | |
C18 | 0.7384 (2) | −0.0108 (3) | 0.03668 (14) | 0.0460 (6) | |
H18 | 0.8009 | −0.0820 | 0.0437 | 0.055* | |
C19 | 0.6976 (2) | 0.0470 (3) | 0.09217 (13) | 0.0409 (6) | |
H19 | 0.7341 | 0.0119 | 0.1359 | 0.049* | |
C20 | 0.5559 (2) | 0.1972 (2) | 0.02186 (11) | 0.0324 (5) | |
C21 | 0.4581 (2) | 0.3058 (2) | 0.01486 (11) | 0.0325 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Mn1 | 0.0330 (2) | 0.0325 (2) | 0.0270 (2) | −0.00107 (15) | 0.00467 (15) | 0.00219 (14) |
O1 | 0.0355 (9) | 0.0314 (8) | 0.0341 (9) | −0.0038 (7) | −0.0005 (7) | 0.0018 (7) |
O2 | 0.0453 (10) | 0.0347 (9) | 0.0415 (10) | −0.0032 (8) | −0.0030 (8) | 0.0073 (8) |
O3 | 0.0431 (10) | 0.0274 (8) | 0.0411 (9) | 0.0065 (7) | 0.0122 (7) | 0.0063 (7) |
O4 | 0.0385 (9) | 0.0304 (8) | 0.0417 (9) | 0.0027 (7) | 0.0138 (7) | 0.0070 (7) |
O5 | 0.0679 (13) | 0.0348 (10) | 0.0528 (11) | −0.0137 (9) | −0.0134 (10) | 0.0148 (8) |
O6 | 0.237 (6) | 0.155 (4) | 0.233 (5) | 0.068 (4) | −0.113 (5) | 0.021 (4) |
N1 | 0.0356 (11) | 0.0339 (10) | 0.0314 (10) | −0.0014 (9) | 0.0083 (8) | 0.0032 (8) |
N2 | 0.0309 (10) | 0.0330 (10) | 0.0321 (10) | −0.0043 (8) | 0.0038 (8) | −0.0012 (8) |
C1 | 0.0391 (15) | 0.0310 (13) | 0.0708 (19) | −0.0047 (11) | 0.0034 (13) | −0.0074 (12) |
C2 | 0.0433 (16) | 0.0600 (17) | 0.0455 (16) | −0.0031 (13) | −0.0040 (12) | −0.0130 (14) |
C3 | 0.0357 (14) | 0.0533 (17) | 0.0481 (16) | −0.0010 (12) | −0.0051 (12) | 0.0004 (13) |
C4 | 0.0270 (12) | 0.0393 (14) | 0.0585 (16) | −0.0004 (10) | 0.0043 (11) | −0.0032 (12) |
C5 | 0.0305 (12) | 0.0343 (12) | 0.0375 (13) | −0.0002 (10) | 0.0101 (10) | 0.0010 (10) |
C6 | 0.0363 (13) | 0.0294 (12) | 0.0377 (13) | −0.0027 (10) | 0.0072 (10) | 0.0048 (10) |
C7 | 0.0339 (15) | 0.0512 (16) | 0.074 (2) | −0.0115 (12) | 0.0065 (13) | 0.0001 (15) |
C8 | 0.0332 (12) | 0.0291 (12) | 0.0318 (12) | 0.0034 (10) | 0.0091 (10) | −0.0012 (10) |
C9 | 0.0349 (12) | 0.0267 (11) | 0.0234 (11) | 0.0001 (9) | 0.0041 (9) | −0.0002 (9) |
C10 | 0.0438 (15) | 0.0408 (14) | 0.0414 (14) | 0.0023 (12) | 0.0135 (12) | 0.0044 (11) |
C11 | 0.0409 (15) | 0.0402 (14) | 0.0562 (17) | 0.0037 (12) | 0.0056 (12) | 0.0111 (13) |
C12 | 0.0530 (16) | 0.0404 (14) | 0.0385 (14) | −0.0052 (12) | −0.0046 (12) | 0.0087 (11) |
C13 | 0.0503 (15) | 0.0315 (12) | 0.0315 (13) | −0.0101 (11) | 0.0018 (11) | 0.0036 (10) |
C14 | 0.072 (2) | 0.0453 (15) | 0.0252 (13) | −0.0095 (14) | 0.0020 (12) | 0.0010 (11) |
C15 | 0.0690 (19) | 0.0431 (14) | 0.0318 (13) | −0.0115 (14) | 0.0154 (13) | −0.0085 (11) |
C16 | 0.0475 (15) | 0.0343 (13) | 0.0337 (13) | −0.0142 (11) | 0.0108 (11) | −0.0083 (10) |
C17 | 0.0453 (15) | 0.0447 (15) | 0.0499 (16) | −0.0100 (12) | 0.0168 (13) | −0.0185 (12) |
C18 | 0.0354 (14) | 0.0424 (15) | 0.0586 (17) | −0.0022 (12) | 0.0076 (12) | −0.0163 (13) |
C19 | 0.0333 (13) | 0.0414 (14) | 0.0432 (14) | −0.0018 (11) | −0.0007 (11) | −0.0028 (11) |
C20 | 0.0365 (13) | 0.0283 (11) | 0.0313 (12) | −0.0105 (10) | 0.0060 (10) | −0.0022 (9) |
C21 | 0.0391 (13) | 0.0278 (11) | 0.0292 (12) | −0.0102 (10) | 0.0052 (10) | 0.0000 (9) |
Geometric parameters (Å, º) top
Mn1—O1 | 2.0992 (16) | C4—C5 | 1.556 (3) |
Mn1—O5 | 2.1384 (18) | C4—H4 | 0.9800 |
Mn1—O3i | 2.2165 (17) | C5—C8 | 1.522 (3) |
Mn1—N2 | 2.2633 (19) | C5—C6 | 1.563 (3) |
Mn1—O4i | 2.3015 (16) | C5—H5 | 0.9800 |
Mn1—N1 | 2.3045 (19) | C6—C9 | 1.513 (3) |
Mn1—Mn1i | 5.6983 (10) | C6—H6 | 0.9800 |
O1—C8 | 1.270 (3) | C7—H7A | 0.9700 |
O2—C8 | 1.243 (3) | C7—H7B | 0.9700 |
O3—C9 | 1.274 (3) | C10—C11 | 1.391 (3) |
O3—Mn1ii | 2.2165 (17) | C10—H10 | 0.9300 |
O4—C9 | 1.240 (3) | C11—C12 | 1.361 (4) |
O4—Mn1ii | 2.3015 (16) | C11—H11 | 0.9300 |
O5—H5A | 0.8200 | C12—C13 | 1.403 (4) |
O5—H5B | 0.8200 | C12—H12 | 0.9300 |
O6—H6A | 0.8200 | C13—C21 | 1.404 (3) |
O6—H6B | 0.8200 | C13—C14 | 1.434 (4) |
N1—C10 | 1.323 (3) | C14—C15 | 1.343 (4) |
N1—C21 | 1.356 (3) | C14—H14 | 0.9300 |
N2—C19 | 1.322 (3) | C15—C16 | 1.428 (4) |
N2—C20 | 1.354 (3) | C15—H15 | 0.9300 |
C1—C2 | 1.499 (4) | C16—C17 | 1.403 (4) |
C1—C7 | 1.538 (4) | C16—C20 | 1.406 (3) |
C1—C6 | 1.571 (3) | C17—C18 | 1.363 (4) |
C1—H1 | 0.9800 | C17—H17 | 0.9300 |
C2—C3 | 1.312 (4) | C18—C19 | 1.394 (4) |
C2—H2 | 0.9300 | C18—H18 | 0.9300 |
C3—C4 | 1.505 (4) | C19—H19 | 0.9300 |
C3—H3 | 0.9300 | C20—C21 | 1.441 (3) |
C4—C7 | 1.542 (4) | | |
| | | |
O1—Mn1—O5 | 86.91 (7) | C1—C6—H6 | 108.5 |
O1—Mn1—O3i | 98.63 (6) | C1—C7—C4 | 92.9 (2) |
O5—Mn1—O3i | 108.27 (7) | C1—C7—H7A | 113.1 |
O1—Mn1—N2 | 104.11 (7) | C4—C7—H7A | 113.1 |
O5—Mn1—N2 | 88.88 (8) | C1—C7—H7B | 113.1 |
O3i—Mn1—N2 | 152.23 (7) | C4—C7—H7B | 113.1 |
O1—Mn1—O4i | 153.64 (6) | H7A—C7—H7B | 110.5 |
O5—Mn1—O4i | 89.91 (7) | O2—C8—O1 | 124.8 (2) |
O3i—Mn1—O4i | 57.73 (6) | O2—C8—C5 | 120.2 (2) |
N2—Mn1—O4i | 101.98 (6) | O1—C8—C5 | 114.80 (19) |
O1—Mn1—N1 | 103.44 (6) | O4—C9—O3 | 120.5 (2) |
O5—Mn1—N1 | 160.44 (7) | O4—C9—C6 | 122.1 (2) |
O3i—Mn1—N1 | 86.83 (7) | O3—C9—C6 | 117.35 (19) |
N2—Mn1—N1 | 72.62 (7) | N1—C10—C11 | 123.7 (2) |
O4i—Mn1—N1 | 87.83 (6) | N1—C10—H10 | 118.2 |
C10—N1—C21 | 117.5 (2) | C11—C10—H10 | 118.2 |
C10—N1—Mn1 | 127.39 (16) | C12—C11—C10 | 119.1 (3) |
C21—N1—Mn1 | 115.10 (15) | C12—C11—H11 | 120.5 |
C19—N2—C20 | 117.7 (2) | C10—C11—H11 | 120.5 |
C19—N2—Mn1 | 125.63 (16) | C11—C12—C13 | 119.5 (2) |
C20—N2—Mn1 | 116.63 (15) | C11—C12—H12 | 120.2 |
C2—C1—C7 | 100.5 (2) | C13—C12—H12 | 120.2 |
C2—C1—C6 | 107.1 (2) | C12—C13—C21 | 117.4 (2) |
C7—C1—C6 | 100.4 (2) | C12—C13—C14 | 123.4 (2) |
C2—C1—H1 | 115.6 | C21—C13—C14 | 119.2 (2) |
C7—C1—H1 | 115.6 | C15—C14—C13 | 121.4 (2) |
C6—C1—H1 | 115.6 | C15—C14—H14 | 119.3 |
C3—C2—C1 | 107.4 (3) | C13—C14—H14 | 119.3 |
C3—C2—H2 | 126.3 | C14—C15—C16 | 120.8 (2) |
C1—C2—H2 | 126.3 | C14—C15—H15 | 119.6 |
C2—C3—C4 | 108.3 (3) | C16—C15—H15 | 119.6 |
C2—C3—H3 | 125.9 | C17—C16—C20 | 117.6 (2) |
C4—C3—H3 | 125.9 | C17—C16—C15 | 122.8 (2) |
C3—C4—C7 | 100.0 (2) | C20—C16—C15 | 119.6 (2) |
C3—C4—C5 | 108.4 (2) | C18—C17—C16 | 119.3 (2) |
C7—C4—C5 | 99.2 (2) | C18—C17—H17 | 120.3 |
C3—C4—H4 | 115.7 | C16—C17—H17 | 120.3 |
C7—C4—H4 | 115.7 | C17—C18—C19 | 119.1 (2) |
C5—C4—H4 | 115.7 | C17—C18—H18 | 120.5 |
C8—C5—C4 | 117.55 (19) | C19—C18—H18 | 120.5 |
C8—C5—C6 | 118.22 (18) | N2—C19—C18 | 123.5 (2) |
C4—C5—C6 | 102.72 (18) | N2—C19—H19 | 118.2 |
C8—C5—H5 | 105.7 | C18—C19—H19 | 118.2 |
C4—C5—H5 | 105.7 | N2—C20—C16 | 122.7 (2) |
C6—C5—H5 | 105.7 | N2—C20—C21 | 117.8 (2) |
C9—C6—C5 | 117.98 (18) | C16—C20—C21 | 119.5 (2) |
C9—C6—C1 | 110.9 (2) | N1—C21—C13 | 122.8 (2) |
C5—C6—C1 | 101.96 (19) | N1—C21—C20 | 117.8 (2) |
C9—C6—H6 | 108.5 | C13—C21—C20 | 119.3 (2) |
C5—C6—H6 | 108.5 | | |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O2 | 0.82 | 1.91 | 2.666 (2) | 152 |
O5—H5B···O3iii | 0.82 | 1.87 | 2.677 (2) | 169 |
O6—H6A···O2 | 0.82 | 2.06 | 2.773 (4) | 145 |
Symmetry code: (iii) x, y−1, z. |