In the title compound, [Mn(C
3H
4N
2)
6](C
8H
4O
4)·4H
2O, the Mn atom is in an octahedral geometry formed by the tertiary N atoms of the imidazole moieties. The Mn atom lies on an inversion centre, as does the centroid of the terephthalate ring.The molecules are connected into a three-dimensional network by intermolecular interactions. The packing is further stabilized by C—H
π interactions.
Supporting information
CCDC reference: 212704
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.036
- wR factor = 0.100
- Data-to-parameter ratio = 12.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.96 Deg.
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT354_ALERT_3_C Short O-H Bond (0.82A) O1W - H1W1 = 0.70 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B .. CG1 = 2.95 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9A .. CG2 = 2.91 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
Hexaimidazolemanganese(II) terephthalate tetrahydrate
top
Crystal data top
[Mn(C3H4N2)6](C8H4O4)·4H2O | F(000) = 730 |
Mr = 699.61 | Dx = 1.416 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2286 reflections |
a = 13.050 (3) Å | θ = 1.6–25.0° |
b = 16.068 (3) Å | µ = 0.47 mm−1 |
c = 8.0948 (16) Å | T = 293 K |
β = 104.75 (3)° | Block, colorless |
V = 1641.4 (6) Å3 | 0.24 × 0.22 × 0.18 mm |
Z = 2 | |
Data collection top
Bruker SMART 1000 CCD diffractometer | 2882 independent reflections |
Radiation source: fine-focus sealed tube | 2286 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 1.6° |
ω scans | h = −14→15 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = 0→19 |
Tmin = 0.896, Tmax = 0.921 | l = −9→0 |
3102 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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.028P)2 + 0.8199P] where P = (Fo2 + 2Fc2)/3 |
2882 reflections | (Δ/σ)max < 0.001 |
230 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.50 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 | 0.5000 | 0.0000 | 0.0000 | 0.03132 (15) | |
N1 | 0.55843 (16) | −0.10915 (12) | 0.1782 (3) | 0.0403 (5) | |
N2 | 0.66322 (18) | −0.20173 (14) | 0.3351 (3) | 0.0507 (6) | |
H2A | 0.7190 | −0.2309 | 0.3776 | 0.061* | |
N3 | 0.60200 (15) | 0.08750 (13) | 0.1985 (3) | 0.0407 (5) | |
N4 | 0.72047 (18) | 0.18101 (15) | 0.3149 (3) | 0.0566 (6) | |
H4A | 0.7600 | 0.2245 | 0.3256 | 0.068* | |
N5 | 0.36016 (15) | 0.01824 (13) | 0.1115 (3) | 0.0394 (5) | |
N6 | 0.19725 (15) | 0.01964 (13) | 0.1368 (3) | 0.0440 (5) | |
H6A | 0.1305 | 0.0092 | 0.1161 | 0.053* | |
O1 | 0.97816 (15) | 0.68804 (11) | 0.2502 (2) | 0.0475 (5) | |
O2 | 1.03711 (15) | 0.58608 (10) | 0.4299 (2) | 0.0470 (4) | |
C1 | 0.5047 (2) | −0.15101 (18) | 0.2788 (3) | 0.0520 (7) | |
H1A | 0.4345 | −0.1415 | 0.2796 | 0.062* | |
C2 | 0.5688 (2) | −0.20770 (19) | 0.3750 (4) | 0.0614 (8) | |
H2B | 0.5518 | −0.2437 | 0.4538 | 0.074* | |
C3 | 0.6536 (2) | −0.14251 (16) | 0.2177 (3) | 0.0460 (6) | |
H3A | 0.7078 | −0.1265 | 0.1688 | 0.055* | |
C4 | 0.6454 (2) | 0.06786 (19) | 0.3667 (3) | 0.0518 (7) | |
H4B | 0.6270 | 0.0218 | 0.4227 | 0.062* | |
C5 | 0.7186 (2) | 0.1248 (2) | 0.4387 (4) | 0.0626 (8) | |
H5A | 0.7597 | 0.1254 | 0.5509 | 0.075* | |
C6 | 0.6498 (2) | 0.15670 (16) | 0.1739 (3) | 0.0459 (6) | |
H6B | 0.6360 | 0.1851 | 0.0705 | 0.055* | |
C7 | 0.3548 (2) | 0.06562 (17) | 0.2508 (3) | 0.0448 (6) | |
H7A | 0.4119 | 0.0930 | 0.3226 | 0.054* | |
C8 | 0.2547 (2) | 0.06639 (19) | 0.2670 (3) | 0.0515 (7) | |
H8A | 0.2301 | 0.0935 | 0.3508 | 0.062* | |
C9 | 0.26265 (18) | −0.00729 (16) | 0.0470 (3) | 0.0426 (6) | |
H9A | 0.2419 | −0.0403 | −0.0502 | 0.051* | |
C10 | 1.00788 (17) | 0.61441 (14) | 0.2822 (3) | 0.0320 (5) | |
C11 | 1.00464 (16) | 0.55529 (14) | 0.1356 (3) | 0.0309 (5) | |
C12 | 0.98386 (19) | 0.58406 (15) | −0.0325 (3) | 0.0396 (6) | |
H12A | 0.9727 | 0.6406 | −0.0551 | 0.047* | |
C13 | 1.0202 (2) | 0.47094 (15) | 0.1655 (3) | 0.0384 (6) | |
H13A | 1.0336 | 0.4509 | 0.2767 | 0.046* | |
O2W | 0.13014 (17) | 0.80294 (14) | 0.1865 (3) | 0.0544 (5) | |
O1W | 0.84840 (17) | 0.78198 (15) | 0.0009 (3) | 0.0575 (6) | |
H2W2 | 0.099 (3) | 0.831 (2) | 0.106 (5) | 0.076 (12)* | |
H2W1 | 0.890 (3) | 0.750 (3) | 0.084 (5) | 0.109 (14)* | |
H1W2 | 0.086 (3) | 0.771 (2) | 0.206 (5) | 0.089 (14)* | |
H1W1 | 0.882 (3) | 0.794 (2) | −0.050 (5) | 0.079 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Mn1 | 0.0266 (2) | 0.0374 (3) | 0.0304 (3) | −0.0029 (2) | 0.00814 (19) | −0.0011 (2) |
N1 | 0.0398 (11) | 0.0408 (11) | 0.0392 (11) | −0.0003 (9) | 0.0083 (9) | 0.0021 (9) |
N2 | 0.0495 (13) | 0.0435 (12) | 0.0517 (13) | 0.0058 (10) | −0.0005 (11) | 0.0052 (11) |
N3 | 0.0358 (11) | 0.0473 (12) | 0.0388 (11) | −0.0052 (9) | 0.0092 (9) | −0.0065 (9) |
N4 | 0.0428 (13) | 0.0514 (14) | 0.0730 (17) | −0.0117 (11) | 0.0098 (12) | −0.0230 (13) |
N5 | 0.0310 (10) | 0.0490 (13) | 0.0401 (11) | −0.0014 (9) | 0.0122 (9) | −0.0003 (9) |
N6 | 0.0278 (10) | 0.0526 (13) | 0.0552 (13) | 0.0012 (9) | 0.0175 (9) | 0.0013 (10) |
O1 | 0.0687 (12) | 0.0364 (10) | 0.0359 (9) | 0.0094 (9) | 0.0102 (8) | 0.0004 (8) |
O2 | 0.0710 (12) | 0.0405 (10) | 0.0276 (9) | 0.0037 (9) | 0.0088 (8) | 0.0013 (7) |
C1 | 0.0478 (15) | 0.0567 (17) | 0.0523 (16) | −0.0030 (13) | 0.0143 (13) | 0.0125 (14) |
C2 | 0.0623 (19) | 0.0612 (19) | 0.0586 (18) | −0.0024 (15) | 0.0116 (15) | 0.0228 (15) |
C3 | 0.0422 (14) | 0.0471 (15) | 0.0471 (15) | 0.0013 (12) | 0.0082 (12) | 0.0015 (12) |
C4 | 0.0499 (16) | 0.0656 (18) | 0.0360 (14) | −0.0101 (14) | 0.0036 (12) | −0.0040 (13) |
C5 | 0.0525 (17) | 0.079 (2) | 0.0472 (17) | −0.0057 (16) | −0.0033 (13) | −0.0172 (16) |
C6 | 0.0441 (14) | 0.0443 (15) | 0.0486 (15) | −0.0044 (12) | 0.0105 (12) | −0.0096 (12) |
C7 | 0.0382 (13) | 0.0568 (16) | 0.0389 (14) | 0.0013 (12) | 0.0090 (11) | −0.0035 (12) |
C8 | 0.0437 (15) | 0.0704 (19) | 0.0434 (15) | 0.0095 (14) | 0.0167 (12) | −0.0062 (14) |
C9 | 0.0337 (13) | 0.0472 (15) | 0.0490 (15) | −0.0023 (11) | 0.0145 (11) | −0.0075 (12) |
C10 | 0.0271 (11) | 0.0376 (13) | 0.0328 (12) | −0.0031 (9) | 0.0105 (9) | 0.0006 (10) |
C11 | 0.0286 (11) | 0.0352 (12) | 0.0317 (11) | −0.0006 (9) | 0.0131 (9) | 0.0023 (10) |
C12 | 0.0550 (15) | 0.0310 (12) | 0.0350 (13) | 0.0049 (11) | 0.0157 (11) | 0.0037 (10) |
C13 | 0.0522 (15) | 0.0378 (13) | 0.0265 (12) | 0.0024 (11) | 0.0125 (11) | 0.0060 (10) |
O2W | 0.0481 (12) | 0.0496 (12) | 0.0574 (13) | 0.0034 (10) | −0.0016 (10) | 0.0115 (10) |
O1W | 0.0443 (12) | 0.0634 (14) | 0.0606 (14) | −0.0040 (10) | 0.0056 (11) | 0.0195 (11) |
Geometric parameters (Å, º) top
Mn1—N5i | 2.251 (2) | C1—C2 | 1.343 (4) |
Mn1—N5 | 2.251 (2) | C1—H1A | 0.93 |
Mn1—N1 | 2.276 (2) | C2—H2B | 0.93 |
Mn1—N1i | 2.276 (2) | C3—H3A | 0.93 |
Mn1—N3i | 2.289 (2) | C4—C5 | 1.343 (4) |
Mn1—N3 | 2.289 (2) | C4—H4B | 0.93 |
N1—C3 | 1.315 (3) | C5—H5A | 0.93 |
N1—C1 | 1.377 (3) | C6—H6B | 0.93 |
N2—C3 | 1.328 (3) | C7—C8 | 1.346 (4) |
N2—C2 | 1.354 (4) | C7—H7A | 0.93 |
N2—H2A | 0.86 | C8—H8A | 0.93 |
N3—C6 | 1.315 (3) | C9—H9A | 0.93 |
N3—C4 | 1.372 (3) | C10—C11 | 1.512 (3) |
N4—C6 | 1.330 (3) | C11—C13 | 1.383 (3) |
N4—C5 | 1.354 (4) | C11—C12 | 1.397 (3) |
N4—H4A | 0.86 | C12—C13ii | 1.383 (3) |
N5—C9 | 1.312 (3) | C12—H12A | 0.93 |
N5—C7 | 1.377 (3) | C13—C12ii | 1.383 (3) |
N6—C9 | 1.326 (3) | C13—H13A | 0.93 |
N6—C8 | 1.355 (3) | O2W—H2W2 | 0.82 (4) |
N6—H6A | 0.86 | O2W—H1W2 | 0.81 (4) |
O1—C10 | 1.251 (3) | O1W—H2W1 | 0.91 (4) |
O2—C10 | 1.245 (3) | O1W—H1W1 | 0.71 (4) |
| | | |
N5i—Mn1—N5 | 180.00 (4) | C1—C2—H2B | 126.7 |
N5i—Mn1—N1 | 88.79 (7) | N2—C2—H2B | 126.8 |
N5—Mn1—N1 | 91.21 (7) | N1—C3—N2 | 112.1 (2) |
N5i—Mn1—N1i | 91.21 (7) | N1—C3—H3A | 123.8 |
N5—Mn1—N1i | 88.79 (7) | N2—C3—H3A | 124.0 |
N1—Mn1—N1i | 180.00 (12) | C5—C4—N3 | 110.0 (3) |
N5i—Mn1—N3i | 91.41 (7) | C5—C4—H4B | 125.0 |
N5—Mn1—N3i | 88.59 (7) | N3—C4—H4B | 125.0 |
N1—Mn1—N3i | 90.72 (8) | C4—C5—N4 | 106.2 (3) |
N1i—Mn1—N3i | 89.28 (8) | C4—C5—H5A | 126.9 |
N5i—Mn1—N3 | 88.59 (7) | N4—C5—H5A | 126.9 |
N5—Mn1—N3 | 91.41 (7) | N3—C6—N4 | 111.8 (3) |
N1—Mn1—N3 | 89.28 (8) | N3—C6—H6B | 124.1 |
N1i—Mn1—N3 | 90.72 (8) | N4—C6—H6B | 124.1 |
N3i—Mn1—N3 | 180.00 (11) | C8—C7—N5 | 109.7 (2) |
C3—N1—C1 | 104.4 (2) | C8—C7—H7A | 125.2 |
C3—N1—Mn1 | 127.67 (17) | N5—C7—H7A | 125.0 |
C1—N1—Mn1 | 127.76 (17) | C7—C8—N6 | 106.1 (2) |
C3—N2—C2 | 107.2 (2) | C7—C8—H8A | 126.9 |
C3—N2—H2A | 126.3 | N6—C8—H8A | 127.0 |
C2—N2—H2A | 126.5 | N5—C9—N6 | 112.0 (2) |
C6—N3—C4 | 104.6 (2) | N5—C9—H9A | 123.9 |
C6—N3—Mn1 | 128.83 (17) | N6—C9—H9A | 124.1 |
C4—N3—Mn1 | 125.07 (18) | O2—C10—O1 | 123.2 (2) |
C6—N4—C5 | 107.4 (2) | O2—C10—C11 | 117.7 (2) |
C6—N4—H4A | 126.3 | O1—C10—C11 | 119.1 (2) |
C5—N4—H4A | 126.2 | C13—C11—C12 | 118.6 (2) |
C9—N5—C7 | 104.6 (2) | C13—C11—C10 | 120.3 (2) |
C9—N5—Mn1 | 127.09 (17) | C12—C11—C10 | 121.1 (2) |
C7—N5—Mn1 | 127.97 (16) | C13ii—C12—C11 | 120.4 (2) |
C9—N6—C8 | 107.5 (2) | C13ii—C12—H12A | 119.8 |
C9—N6—H6A | 126.2 | C11—C12—H12A | 119.8 |
C8—N6—H6A | 126.3 | C11—C13—C12ii | 121.0 (2) |
C2—C1—N1 | 109.8 (3) | C11—C13—H13A | 119.5 |
C2—C1—H1A | 125.2 | C12ii—C13—H13A | 119.5 |
N1—C1—H1A | 125.1 | H2W2—O2W—H1W2 | 105 (3) |
C1—C2—N2 | 106.5 (3) | H2W1—O1W—H1W1 | 104 (4) |
| | | |
N5i—Mn1—N1—C3 | 17.5 (2) | C3—N2—C2—C1 | 0.0 (3) |
N5—Mn1—N1—C3 | −162.5 (2) | C1—N1—C3—N2 | −0.1 (3) |
N3i—Mn1—N1—C3 | 108.9 (2) | Mn1—N1—C3—N2 | 175.52 (16) |
N3—Mn1—N1—C3 | −71.1 (2) | C2—N2—C3—N1 | 0.1 (3) |
N5i—Mn1—N1—C1 | −167.8 (2) | C6—N3—C4—C5 | −0.6 (3) |
N5—Mn1—N1—C1 | 12.2 (2) | Mn1—N3—C4—C5 | 166.6 (2) |
N3i—Mn1—N1—C1 | −76.4 (2) | N3—C4—C5—N4 | 0.6 (3) |
N3—Mn1—N1—C1 | 103.6 (2) | C6—N4—C5—C4 | −0.3 (3) |
N5i—Mn1—N3—C6 | 59.1 (2) | C4—N3—C6—N4 | 0.5 (3) |
N5—Mn1—N3—C6 | −120.9 (2) | Mn1—N3—C6—N4 | −166.06 (17) |
N1—Mn1—N3—C6 | 147.9 (2) | C5—N4—C6—N3 | −0.1 (3) |
N1i—Mn1—N3—C6 | −32.1 (2) | C9—N5—C7—C8 | 0.7 (3) |
N5i—Mn1—N3—C4 | −104.9 (2) | Mn1—N5—C7—C8 | 174.44 (18) |
N5—Mn1—N3—C4 | 75.1 (2) | N5—C7—C8—N6 | −0.3 (3) |
N1—Mn1—N3—C4 | −16.1 (2) | C9—N6—C8—C7 | −0.2 (3) |
N1i—Mn1—N3—C4 | 163.9 (2) | C7—N5—C9—N6 | −0.8 (3) |
N1—Mn1—N5—C9 | −99.6 (2) | Mn1—N5—C9—N6 | −174.65 (16) |
N1i—Mn1—N5—C9 | 80.4 (2) | C8—N6—C9—N5 | 0.6 (3) |
N3i—Mn1—N5—C9 | −8.9 (2) | O2—C10—C11—C13 | 8.3 (3) |
N3—Mn1—N5—C9 | 171.1 (2) | O1—C10—C11—C13 | −169.4 (2) |
N1—Mn1—N5—C7 | 88.0 (2) | O2—C10—C11—C12 | −173.0 (2) |
N1i—Mn1—N5—C7 | −92.0 (2) | O1—C10—C11—C12 | 9.3 (3) |
N3i—Mn1—N5—C7 | 178.7 (2) | C13—C11—C12—C13ii | −0.4 (4) |
N3—Mn1—N5—C7 | −1.3 (2) | C10—C11—C12—C13ii | −179.1 (2) |
C3—N1—C1—C2 | 0.1 (3) | C12—C11—C13—C12ii | 0.4 (4) |
Mn1—N1—C1—C2 | −175.5 (2) | C10—C11—C13—C12ii | 179.1 (2) |
N1—C1—C2—N2 | −0.1 (3) | | |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1Wiii | 0.86 | 1.91 | 2.766 (3) | 171 |
N4—H4A···O2Wiv | 0.86 | 1.93 | 2.766 (3) | 164 |
O1W—H1W1···O1v | 0.70 (4) | 2.30 (4) | 2.995 (3) | 169 (4) |
O2W—H1W2···O1vi | 0.82 (4) | 2.04 (4) | 2.851 (3) | 178 (4) |
O1W—H2W1···O1 | 0.91 (4) | 1.83 (4) | 2.735 (3) | 178 (4) |
O2W—H2W2···O2vii | 0.81 (4) | 1.97 (4) | 2.772 (3) | 171 (3) |
C5—H5A···O2Wviii | 0.93 | 2.52 | 3.376 (4) | 153 |
C2—H2B···Cg1ix | 0.93 | 2.95 | 3.816 (3) | 156 |
C9—H9A···Cg2i | 0.93 | 2.91 | 3.668 (3) | 140 |
Symmetry codes: (i) −x+1, −y, −z; (iii) x, −y+1/2, z+1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+3/2, z−1/2; (vi) x−1, y, z; (vii) x−1, −y+3/2, z−1/2; (viii) −x+1, −y+1, −z+1; (ix) x, −y−1/2, z+1/2. |