Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038111/lh2470sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038111/lh2470Isup2.hkl |
CCDC reference: 660253
Chemicals of reagent grade were used without further purification. The ligand N,N,N ', N' - tetrakis (2 '-benzimidazolyl methyl) -1,2-ethanediamine (EDTB) was synthesized from reported literature earlier (Hendriks, et al.,1982). The title pink salt was obtained unexpectedly by reacting EDTB (0.29 g, 0.5 mmol) in 20 ml hot methanol with Mn (NO3)2 ˙4H2O (0.25 g, 1.0 mmol) solution of 10 ml H2O. The mixture was stirred for 1 h at 303k and then filtered. The resulting pink solution was allowed to stand at room temperature for 1 week. Crystals suitale for X-ray analysis were obtained at the bottom of the vessel.
All H atoms bonded to carbon atoms were located at their ideal positions with C–H = 0.96 Å (methyl), 0.93 Å (aromatic), 0.97 Å (methylene) and with Uiso(H)=1.5Ueq(C, methyl) or 1.2Ueq(C, aromatic and methylene). H atoms bonded to N and O atoms were located in difference Fourier maps and refined with distance constraints of N–H =0.86 (4) Å, O–H = 0.82 (4) Å, H–H = 1.35 (4) Å (water H) and their Uiso values were set 1.2 (for imine) or 1.5 (for water and hydroxyl) times that of their carrier atoms.
As part of our continuing studies on the ligands or metal complexes containing multi-benzimidazole groups (Chen et al., 2004;Liao et al.,2001), we report here the crystal structure of the related title compound, which was obtained unexpectedly by reacting N,N,N ', N' - tetrakis (2 '-benzimidazolyl methyl) -1,2-ethanediamine (EDTB) with Mn (NO3)2 ˙4H2O in CH3OH and H2O solution.
In the molecule (Fig. 1), the N2/N3/C3—C9 benzimidazole ring is twisted from the benzimidazole ring (N4/N5/C11—C17) by a dihedral angle of 47.1 (1)°. In the asymmetric unit, there is half of an EDTB molecule, two methanol and one water solvent molecules.
In the supramolecular structure, by a combination of O(or N)–H···O, and O–H···N hydrogen bonds the molecules are linked into a three-dimensional framework (Fig.2). Analysis using PLATON (Spek, 2003) shows that no π–π and C–H···π interactions are observed in the crystal structure.
For related literature, see: Chen et al. (2004); Hendriks et al. (1982); Liao et al. (2001).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
C34H32N10·4CH4O·2H2O | Z = 1 |
Mr = 744.90 | F(000) = 398 |
Triclinic, P1 | Dx = 1.183 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2349 (6) Å | Cell parameters from 3273 reflections |
b = 10.4290 (7) Å | θ = 2.3–24.9° |
c = 11.5344 (8) Å | µ = 0.08 mm−1 |
α = 100.500 (1)° | T = 296 K |
β = 101.763 (1)° | Block, pink |
γ = 99.417 (1)° | 0.20 × 0.20 × 0.10 mm |
V = 1045.83 (12) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 4083 independent reflections |
Radiation source: fine focus sealed Siemens Mo tube | 2726 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.094 |
0.3° wide ω exposures scans | θmax = 26.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −10→11 |
Tmin = 0.984, Tmax = 0.992 | k = −12→12 |
10988 measured reflections | l = −14→14 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.163 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.087P)2] where P = (Fo2 + 2Fc2)/3 |
4083 reflections | (Δ/σ)max < 0.001 |
264 parameters | Δρmax = 0.23 e Å−3 |
7 restraints | Δρmin = −0.26 e Å−3 |
C34H32N10·4CH4O·2H2O | γ = 99.417 (1)° |
Mr = 744.90 | V = 1045.83 (12) Å3 |
Triclinic, P1 | Z = 1 |
a = 9.2349 (6) Å | Mo Kα radiation |
b = 10.4290 (7) Å | µ = 0.08 mm−1 |
c = 11.5344 (8) Å | T = 296 K |
α = 100.500 (1)° | 0.20 × 0.20 × 0.10 mm |
β = 101.763 (1)° |
Bruker SMART APEX CCD area-detector diffractometer | 4083 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | 2726 reflections with I > 2σ(I) |
Tmin = 0.984, Tmax = 0.992 | Rint = 0.094 |
10988 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 7 restraints |
wR(F2) = 0.163 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.23 e Å−3 |
4083 reflections | Δρmin = −0.26 e Å−3 |
264 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.0644 (2) | 0.05926 (17) | 0.52781 (15) | 0.0480 (4) | |
H1A | 0.0399 | 0.1163 | 0.5943 | 0.058* | |
H1B | 0.1549 | 0.0289 | 0.5604 | 0.058* | |
C2 | 0.1912 (2) | 0.0801 (2) | 0.36638 (17) | 0.0568 (5) | |
H2A | 0.1693 | −0.0161 | 0.3554 | 0.068* | |
H2B | 0.2955 | 0.1131 | 0.4118 | 0.068* | |
C3 | 0.1733 (2) | 0.11411 (17) | 0.24450 (16) | 0.0503 (5) | |
C4 | 0.0658 (2) | 0.16310 (17) | 0.07461 (16) | 0.0545 (5) | |
C5 | −0.0262 (3) | 0.1985 (2) | −0.01979 (18) | 0.0683 (6) | |
H5 | −0.1238 | 0.2093 | −0.0182 | 0.082* | |
C6 | 0.0359 (4) | 0.2169 (2) | −0.11684 (19) | 0.0812 (7) | |
H6 | −0.0208 | 0.2428 | −0.1815 | 0.097* | |
C7 | 0.1793 (4) | 0.1977 (3) | −0.1200 (2) | 0.0887 (8) | |
H7 | 0.2159 | 0.2091 | −0.1876 | 0.106* | |
C8 | 0.2696 (3) | 0.1622 (2) | −0.0263 (2) | 0.0758 (7) | |
H8 | 0.3660 | 0.1491 | −0.0295 | 0.091* | |
C9 | 0.2119 (2) | 0.14626 (18) | 0.07405 (17) | 0.0567 (5) | |
C10 | 0.1497 (2) | 0.27781 (18) | 0.49058 (18) | 0.0553 (5) | |
H10A | 0.1750 | 0.3237 | 0.4291 | 0.066* | |
H10B | 0.2408 | 0.2903 | 0.5542 | 0.066* | |
C11 | 0.0337 (2) | 0.33503 (17) | 0.54216 (17) | 0.0504 (5) | |
C12 | −0.0839 (2) | 0.43572 (17) | 0.66124 (17) | 0.0550 (5) | |
C13 | −0.1279 (3) | 0.5076 (2) | 0.7564 (2) | 0.0724 (6) | |
H13 | −0.0576 | 0.5504 | 0.8287 | 0.087* | |
C14 | −0.2771 (3) | 0.5143 (2) | 0.7419 (2) | 0.0815 (7) | |
H14 | −0.3078 | 0.5633 | 0.8048 | 0.098* | |
C15 | −0.3834 (3) | 0.4495 (2) | 0.6349 (3) | 0.0812 (7) | |
H15 | −0.4841 | 0.4557 | 0.6277 | 0.097* | |
C16 | −0.3428 (3) | 0.3760 (2) | 0.5389 (2) | 0.0719 (6) | |
H16 | −0.4138 | 0.3326 | 0.4671 | 0.086* | |
C17 | −0.1918 (2) | 0.36981 (18) | 0.55440 (18) | 0.0552 (5) | |
C18 | 0.4678 (4) | 0.8728 (4) | 0.2625 (4) | 0.1300 (12) | |
H18A | 0.5412 | 0.8183 | 0.2553 | 0.195* | |
H18B | 0.3708 | 0.8250 | 0.2126 | 0.195* | |
H18C | 0.4617 | 0.8944 | 0.3457 | 0.195* | |
C19 | 0.6472 (5) | 0.4394 (4) | 0.0909 (4) | 0.174 (2) | |
H19A | 0.6046 | 0.5171 | 0.1058 | 0.261* | |
H19B | 0.5715 | 0.3674 | 0.0368 | 0.261* | |
H19C | 0.7307 | 0.4586 | 0.0546 | 0.261* | |
N1 | 0.09316 (17) | 0.13561 (13) | 0.43655 (12) | 0.0474 (4) | |
N2 | 0.27737 (18) | 0.11545 (16) | 0.18230 (14) | 0.0581 (4) | |
N3 | 0.04414 (19) | 0.14113 (15) | 0.18572 (13) | 0.0521 (4) | |
H3A | −0.040 (2) | 0.151 (2) | 0.2111 (18) | 0.063* | |
N4 | 0.05769 (19) | 0.41225 (14) | 0.65166 (14) | 0.0560 (4) | |
N5 | −0.11288 (19) | 0.30662 (16) | 0.48112 (15) | 0.0553 (4) | |
H5A | −0.143 (2) | 0.259 (2) | 0.4045 (18) | 0.066* | |
O1 | 0.75915 (17) | 0.17048 (18) | 0.23664 (15) | 0.0740 (5) | |
H1C | 0.732 (3) | 0.238 (3) | 0.209 (3) | 0.111* | |
H1D | 0.682 (3) | 0.114 (3) | 0.236 (3) | 0.111* | |
O2 | 0.6956 (3) | 0.4047 (2) | 0.1961 (3) | 0.1419 (10) | |
H2C | 0.771 (4) | 0.468 (4) | 0.242 (4) | 0.213* | |
O3 | 0.5088 (2) | 0.9845 (3) | 0.2266 (3) | 0.1536 (11) | |
H3B | 0.444 (5) | 1.036 (5) | 0.228 (5) | 0.230* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0588 (12) | 0.0470 (9) | 0.0433 (9) | 0.0109 (8) | 0.0137 (8) | 0.0211 (7) |
C2 | 0.0630 (13) | 0.0591 (11) | 0.0616 (11) | 0.0201 (10) | 0.0246 (10) | 0.0293 (9) |
C3 | 0.0565 (12) | 0.0468 (10) | 0.0556 (10) | 0.0122 (8) | 0.0237 (9) | 0.0191 (8) |
C4 | 0.0748 (14) | 0.0404 (10) | 0.0487 (10) | 0.0055 (9) | 0.0194 (9) | 0.0117 (8) |
C5 | 0.0903 (16) | 0.0552 (12) | 0.0555 (12) | 0.0125 (11) | 0.0105 (11) | 0.0131 (10) |
C6 | 0.126 (2) | 0.0644 (14) | 0.0463 (12) | 0.0075 (15) | 0.0132 (13) | 0.0163 (10) |
C7 | 0.127 (2) | 0.0845 (17) | 0.0526 (13) | −0.0038 (16) | 0.0335 (15) | 0.0189 (12) |
C8 | 0.0915 (17) | 0.0760 (15) | 0.0612 (13) | 0.0005 (12) | 0.0367 (12) | 0.0132 (11) |
C9 | 0.0719 (14) | 0.0471 (10) | 0.0533 (11) | 0.0031 (9) | 0.0260 (10) | 0.0126 (8) |
C10 | 0.0591 (12) | 0.0495 (10) | 0.0592 (11) | 0.0036 (9) | 0.0151 (9) | 0.0228 (9) |
C11 | 0.0597 (13) | 0.0377 (9) | 0.0538 (10) | 0.0040 (8) | 0.0102 (9) | 0.0193 (8) |
C12 | 0.0716 (14) | 0.0396 (10) | 0.0559 (11) | 0.0100 (9) | 0.0155 (10) | 0.0175 (8) |
C13 | 0.0969 (19) | 0.0534 (12) | 0.0660 (13) | 0.0141 (12) | 0.0204 (12) | 0.0115 (10) |
C14 | 0.105 (2) | 0.0613 (14) | 0.0914 (18) | 0.0244 (14) | 0.0462 (17) | 0.0193 (13) |
C15 | 0.0784 (17) | 0.0675 (14) | 0.109 (2) | 0.0199 (13) | 0.0368 (16) | 0.0287 (14) |
C16 | 0.0683 (15) | 0.0625 (13) | 0.0814 (15) | 0.0101 (11) | 0.0125 (12) | 0.0162 (11) |
C17 | 0.0639 (13) | 0.0443 (10) | 0.0593 (11) | 0.0101 (9) | 0.0143 (10) | 0.0185 (9) |
C18 | 0.103 (2) | 0.124 (3) | 0.196 (4) | 0.043 (2) | 0.055 (2) | 0.079 (3) |
C19 | 0.165 (4) | 0.112 (3) | 0.186 (4) | −0.004 (2) | −0.079 (3) | 0.051 (3) |
N1 | 0.0593 (10) | 0.0430 (8) | 0.0477 (8) | 0.0106 (7) | 0.0202 (7) | 0.0213 (6) |
N2 | 0.0597 (11) | 0.0605 (10) | 0.0618 (10) | 0.0112 (8) | 0.0267 (8) | 0.0206 (8) |
N3 | 0.0592 (11) | 0.0527 (9) | 0.0535 (9) | 0.0142 (8) | 0.0237 (8) | 0.0209 (7) |
N4 | 0.0680 (11) | 0.0435 (8) | 0.0539 (9) | 0.0069 (8) | 0.0099 (8) | 0.0141 (7) |
N5 | 0.0617 (11) | 0.0506 (9) | 0.0496 (9) | 0.0078 (8) | 0.0083 (8) | 0.0102 (7) |
O1 | 0.0586 (10) | 0.0798 (11) | 0.0793 (10) | 0.0146 (8) | 0.0091 (8) | 0.0155 (9) |
O2 | 0.1251 (19) | 0.0802 (13) | 0.171 (2) | −0.0134 (12) | −0.0549 (16) | 0.0371 (14) |
O3 | 0.0777 (15) | 0.147 (2) | 0.290 (3) | 0.0454 (14) | 0.0767 (18) | 0.128 (2) |
C1—N1 | 1.471 (2) | C11—N5 | 1.349 (2) |
C1—C1i | 1.508 (4) | C12—C13 | 1.384 (3) |
C1—H1A | 0.9700 | C12—N4 | 1.391 (3) |
C1—H1B | 0.9700 | C12—C17 | 1.397 (3) |
C2—N1 | 1.452 (2) | C13—C14 | 1.368 (3) |
C2—C3 | 1.495 (2) | C13—H13 | 0.9300 |
C2—H2A | 0.9700 | C14—C15 | 1.389 (4) |
C2—H2B | 0.9700 | C14—H14 | 0.9300 |
C3—N2 | 1.311 (2) | C15—C16 | 1.381 (3) |
C3—N3 | 1.346 (2) | C15—H15 | 0.9300 |
C4—C5 | 1.384 (3) | C16—C17 | 1.383 (3) |
C4—C9 | 1.389 (3) | C16—H16 | 0.9300 |
C4—N3 | 1.390 (2) | C17—N5 | 1.373 (2) |
C5—C6 | 1.386 (3) | C18—O3 | 1.330 (4) |
C5—H5 | 0.9300 | C18—H18A | 0.9600 |
C6—C7 | 1.378 (4) | C18—H18B | 0.9600 |
C6—H6 | 0.9300 | C18—H18C | 0.9600 |
C7—C8 | 1.372 (4) | C19—O2 | 1.340 (4) |
C7—H7 | 0.9300 | C19—H19A | 0.9600 |
C8—C9 | 1.394 (3) | C19—H19B | 0.9600 |
C8—H8 | 0.9300 | C19—H19C | 0.9600 |
C9—N2 | 1.389 (3) | N3—H3A | 0.899 (18) |
C10—N1 | 1.462 (2) | N5—H5A | 0.895 (19) |
C10—C11 | 1.482 (3) | O1—H1C | 0.87 (2) |
C10—H10A | 0.9700 | O1—H1D | 0.84 (2) |
C10—H10B | 0.9700 | O2—H2C | 0.88 (3) |
C11—N4 | 1.323 (2) | O3—H3B | 0.86 (3) |
N1—C1—C1i | 110.60 (17) | C13—C12—C17 | 119.8 (2) |
N1—C1—H1A | 109.5 | N4—C12—C17 | 109.68 (16) |
C1i—C1—H1A | 109.5 | C14—C13—C12 | 118.6 (2) |
N1—C1—H1B | 109.5 | C14—C13—H13 | 120.7 |
C1i—C1—H1B | 109.5 | C12—C13—H13 | 120.7 |
H1A—C1—H1B | 108.1 | C13—C14—C15 | 121.3 (2) |
N1—C2—C3 | 113.09 (14) | C13—C14—H14 | 119.4 |
N1—C2—H2A | 109.0 | C15—C14—H14 | 119.4 |
C3—C2—H2A | 109.0 | C16—C15—C14 | 121.4 (2) |
N1—C2—H2B | 109.0 | C16—C15—H15 | 119.3 |
C3—C2—H2B | 109.0 | C14—C15—H15 | 119.3 |
H2A—C2—H2B | 107.8 | C15—C16—C17 | 117.0 (2) |
N2—C3—N3 | 113.39 (16) | C15—C16—H16 | 121.5 |
N2—C3—C2 | 124.18 (17) | C17—C16—H16 | 121.5 |
N3—C3—C2 | 122.37 (15) | N5—C17—C16 | 132.83 (19) |
C5—C4—C9 | 122.96 (18) | N5—C17—C12 | 105.11 (17) |
C5—C4—N3 | 131.8 (2) | C16—C17—C12 | 122.06 (19) |
C9—C4—N3 | 105.17 (17) | O3—C18—H18A | 109.5 |
C4—C5—C6 | 116.0 (2) | O3—C18—H18B | 109.5 |
C4—C5—H5 | 122.0 | H18A—C18—H18B | 109.5 |
C6—C5—H5 | 122.0 | O3—C18—H18C | 109.5 |
C7—C6—C5 | 121.8 (2) | H18A—C18—H18C | 109.5 |
C7—C6—H6 | 119.1 | H18B—C18—H18C | 109.5 |
C5—C6—H6 | 119.1 | O2—C19—H19A | 109.5 |
C8—C7—C6 | 121.9 (2) | O2—C19—H19B | 109.5 |
C8—C7—H7 | 119.1 | H19A—C19—H19B | 109.5 |
C6—C7—H7 | 119.1 | O2—C19—H19C | 109.5 |
C7—C8—C9 | 117.8 (2) | H19A—C19—H19C | 109.5 |
C7—C8—H8 | 121.1 | H19B—C19—H19C | 109.5 |
C9—C8—H8 | 121.1 | C2—N1—C10 | 112.26 (14) |
N2—C9—C4 | 109.66 (15) | C2—N1—C1 | 111.51 (13) |
N2—C9—C8 | 130.7 (2) | C10—N1—C1 | 111.94 (13) |
C4—C9—C8 | 119.6 (2) | C3—N2—C9 | 105.00 (16) |
N1—C10—C11 | 110.23 (15) | C3—N3—C4 | 106.77 (15) |
N1—C10—H10A | 109.6 | C3—N3—H3A | 129.9 (13) |
C11—C10—H10A | 109.6 | C4—N3—H3A | 123.2 (13) |
N1—C10—H10B | 109.6 | C11—N4—C12 | 104.79 (16) |
C11—C10—H10B | 109.6 | C11—N5—C17 | 107.78 (16) |
H10A—C10—H10B | 108.1 | C11—N5—H5A | 121.4 (13) |
N4—C11—N5 | 112.63 (17) | C17—N5—H5A | 130.7 (13) |
N4—C11—C10 | 125.50 (18) | H1C—O1—H1D | 110 (2) |
N5—C11—C10 | 121.80 (17) | C19—O2—H2C | 109 (3) |
C13—C12—N4 | 130.5 (2) | C18—O3—H3B | 114 (4) |
N1—C2—C3—N2 | 156.56 (17) | C13—C12—C17—C16 | 1.4 (3) |
N1—C2—C3—N3 | −26.3 (3) | N4—C12—C17—C16 | −179.99 (17) |
C9—C4—C5—C6 | −0.1 (3) | C3—C2—N1—C10 | −77.3 (2) |
N3—C4—C5—C6 | 177.65 (19) | C3—C2—N1—C1 | 156.14 (16) |
C4—C5—C6—C7 | 1.5 (3) | C11—C10—N1—C2 | 169.89 (14) |
C5—C6—C7—C8 | −1.4 (4) | C11—C10—N1—C1 | −63.81 (19) |
C6—C7—C8—C9 | −0.3 (4) | C1i—C1—N1—C2 | −84.5 (2) |
C5—C4—C9—N2 | 177.98 (17) | C1i—C1—N1—C10 | 148.77 (19) |
N3—C4—C9—N2 | −0.3 (2) | N3—C3—N2—C9 | 0.2 (2) |
C5—C4—C9—C8 | −1.5 (3) | C2—C3—N2—C9 | 177.57 (17) |
N3—C4—C9—C8 | −179.79 (18) | C4—C9—N2—C3 | 0.0 (2) |
C7—C8—C9—N2 | −177.7 (2) | C8—C9—N2—C3 | 179.5 (2) |
C7—C8—C9—C4 | 1.7 (3) | N2—C3—N3—C4 | −0.4 (2) |
N1—C10—C11—N4 | 132.12 (17) | C2—C3—N3—C4 | −177.79 (16) |
N1—C10—C11—N5 | −44.6 (2) | C5—C4—N3—C3 | −177.6 (2) |
N4—C12—C13—C14 | −179.68 (19) | C9—C4—N3—C3 | 0.38 (19) |
C17—C12—C13—C14 | −1.4 (3) | N5—C11—N4—C12 | −0.37 (19) |
C12—C13—C14—C15 | 0.8 (3) | C10—C11—N4—C12 | −177.35 (15) |
C13—C14—C15—C16 | −0.2 (4) | C13—C12—N4—C11 | 178.59 (18) |
C14—C15—C16—C17 | 0.1 (3) | C17—C12—N4—C11 | 0.16 (18) |
C15—C16—C17—N5 | 179.17 (19) | N4—C11—N5—C17 | 0.4 (2) |
C15—C16—C17—C12 | −0.7 (3) | C10—C11—N5—C17 | 177.55 (14) |
C13—C12—C17—N5 | −178.53 (16) | C16—C17—N5—C11 | 179.8 (2) |
N4—C12—C17—N5 | 0.09 (19) | C12—C17—N5—C11 | −0.30 (18) |
Symmetry code: (i) −x, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1C···O2 | 0.87 (2) | 1.85 (2) | 2.702 (3) | 164 (3) |
O3—H3B···N2ii | 0.86 (3) | 1.90 (4) | 2.731 (2) | 163 (5) |
N5—H5A···O1iii | 0.90 (2) | 1.94 (2) | 2.828 (2) | 170 (2) |
N3—H3A···O1iii | 0.90 (2) | 1.97 (2) | 2.862 (2) | 170 (2) |
O2—H2C···N4iv | 0.88 (3) | 1.89 (3) | 2.765 (3) | 173 (5) |
O1—H1D···O3v | 0.84 (2) | 1.89 (2) | 2.731 (3) | 177 (3) |
Symmetry codes: (ii) x, y+1, z; (iii) x−1, y, z; (iv) −x+1, −y+1, −z+1; (v) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C34H32N10·4CH4O·2H2O |
Mr | 744.90 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 9.2349 (6), 10.4290 (7), 11.5344 (8) |
α, β, γ (°) | 100.500 (1), 101.763 (1), 99.417 (1) |
V (Å3) | 1045.83 (12) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.20 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2001) |
Tmin, Tmax | 0.984, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10988, 4083, 2726 |
Rint | 0.094 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.163, 1.01 |
No. of reflections | 4083 |
No. of parameters | 264 |
No. of restraints | 7 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.26 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1C···O2 | 0.87 (2) | 1.85 (2) | 2.702 (3) | 164 (3) |
O3—H3B···N2i | 0.86 (3) | 1.90 (4) | 2.731 (2) | 163 (5) |
N5—H5A···O1ii | 0.895 (19) | 1.94 (2) | 2.828 (2) | 169.5 (19) |
N3—H3A···O1ii | 0.899 (18) | 1.972 (19) | 2.862 (2) | 170.0 (18) |
O2—H2C···N4iii | 0.88 (3) | 1.89 (3) | 2.765 (3) | 173 (5) |
O1—H1D···O3iv | 0.84 (2) | 1.89 (2) | 2.731 (3) | 177 (3) |
Symmetry codes: (i) x, y+1, z; (ii) x−1, y, z; (iii) −x+1, −y+1, −z+1; (iv) x, y−1, z. |
As part of our continuing studies on the ligands or metal complexes containing multi-benzimidazole groups (Chen et al., 2004;Liao et al.,2001), we report here the crystal structure of the related title compound, which was obtained unexpectedly by reacting N,N,N ', N' - tetrakis (2 '-benzimidazolyl methyl) -1,2-ethanediamine (EDTB) with Mn (NO3)2 ˙4H2O in CH3OH and H2O solution.
In the molecule (Fig. 1), the N2/N3/C3—C9 benzimidazole ring is twisted from the benzimidazole ring (N4/N5/C11—C17) by a dihedral angle of 47.1 (1)°. In the asymmetric unit, there is half of an EDTB molecule, two methanol and one water solvent molecules.
In the supramolecular structure, by a combination of O(or N)–H···O, and O–H···N hydrogen bonds the molecules are linked into a three-dimensional framework (Fig.2). Analysis using PLATON (Spek, 2003) shows that no π–π and C–H···π interactions are observed in the crystal structure.