Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020879/at2277sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020879/at2277Isup2.hkl |
CCDC reference: 650524
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- Disorder in solvent or counterion
- R factor = 0.052
- wR factor = 0.145
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT093_ALERT_1_A No su's on H-atoms, but refinement reported as . mixed
Alert level B PLAT413_ALERT_2_B Short Inter XH3 .. XHn H36B .. H36B .. 2.09 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT221_ALERT_4_C Large Solvent/Anion C Ueq(max)/Ueq(min) ... 3.66 Ratio PLAT223_ALERT_4_C Large Solvent/Anion H Ueq(max)/Ueq(min) ... 3.72 Ratio PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 20.00 Perc.
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 26
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 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 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Chen et al. (2004); Hendriks et al. (1982); Liao et al. (2001).
The ligand N,N,N ',N'-tetrakis (2 '-benzimidazolyl methyl) -,2-ethanediamine (EDTB) was synthesized from reported literature earlier (Hendriks et al., 1982). After, the ligand EDTB (0.58 g, 1.0 mmol) in 20 ml hot absolute methanol was added slowly to the NiCl2. 6H2O (0.24 g, 1.0 mmol) solution of 10 ml me thanol. The mixture was stirred for 1 h. After filtration, the purple solution was allowed to stand at room temperature. Purple block-shaped crystals suitable of (I) for X-ray analysis were obtained in several days in 45% yield.
The atoms of one of the methanol molecules are disordered over two sites; the atoms involved are O3, C37 with their attached H atoms. Site occupancy factors refined to 0.75 (2):0.25 (2). The H atoms bonded C atoms were placed at their idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, with Uiso(H) = 1.2–1.5Ueq(C). H atoms bonded to N atoms were placed at their indicative positions with the Uiso value being set 1.2 times of their carrier atoms, N—H = 0.86 Å. The H atoms of the hydroxyl group were refined with the constraints of O–H = 0.82 Å, and Uiso(H) =1.5Ueq(O).
Recently, study in the ligands containing-polybenzimidazoles and their metal coordination compounds has been widely carried on (Chen et al., 2004; Liao et al., 2001). As the continuing work of our workgroup, we report the crystallography structure of the title compound, [Ni(EDTB)]2Cl-.3CH3OH, (I); {EDTB = N,N,N',N'-tetrakis(2'-benzimidazolyl methyl)-1,2-ethanediamine}.
In the title molecular structure (I), NiII is coordinated by four four benzimidazole nitrogen atoms, two amino N atoms of EDTB, forming a distorted octahedron coordination geometry (Table 1 and Fig. 1).
In the supramolecular structure, there are a number of N(or O)–H···Cl, N–H···O and O–H···N hydrogen bonding interactions which link the molecules into a three-dimensional framwork (Table 2 and Fig.2.).
For related literature, see: Chen et al. (2004); Hendriks et al. (1982); Liao et al. (2001).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
[Ni(C34H32N10)]Cl2·3CH4O | Z = 2 |
Mr = 806.43 | F(000) = 844 |
Triclinic, P1 | Dx = 1.359 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.8183 (5) Å | Cell parameters from 5644 reflections |
b = 11.7267 (6) Å | θ = 0.0–0.0° |
c = 16.8837 (8) Å | µ = 0.68 mm−1 |
α = 74.312 (1)° | T = 298 K |
β = 87.491 (1)° | Block, purple |
γ = 73.065 (1)° | 0.30 × 0.20 × 0.20 mm |
V = 1971.28 (16) Å3 |
Bruker SMART CCD area-detector diffractometer | 6229 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 26.0°, θmin = 1.9° |
φ and ω scans | h = −13→12 |
17041 measured reflections | k = −14→14 |
7670 independent reflections | l = −20→20 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0747P)2 + 0.9889P] where P = (Fo2 + 2Fc2)/3 |
7670 reflections | (Δ/σ)max < 0.001 |
505 parameters | Δρmax = 0.52 e Å−3 |
26 restraints | Δρmin = −0.50 e Å−3 |
[Ni(C34H32N10)]Cl2·3CH4O | γ = 73.065 (1)° |
Mr = 806.43 | V = 1971.28 (16) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.8183 (5) Å | Mo Kα radiation |
b = 11.7267 (6) Å | µ = 0.68 mm−1 |
c = 16.8837 (8) Å | T = 298 K |
α = 74.312 (1)° | 0.30 × 0.20 × 0.20 mm |
β = 87.491 (1)° |
Bruker SMART CCD area-detector diffractometer | 6229 reflections with I > 2σ(I) |
17041 measured reflections | Rint = 0.031 |
7670 independent reflections |
R[F2 > 2σ(F2)] = 0.052 | 26 restraints |
wR(F2) = 0.145 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.52 e Å−3 |
7670 reflections | Δρmin = −0.50 e Å−3 |
505 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 | Occ. (<1) | |
Ni1 | 0.76117 (3) | 0.88541 (3) | 0.73720 (2) | 0.03295 (13) | |
C1 | 0.6510 (3) | 0.8609 (3) | 0.58813 (18) | 0.0418 (7) | |
H1A | 0.5788 | 0.8775 | 0.5505 | 0.050* | |
H1B | 0.7081 | 0.7789 | 0.5909 | 0.050* | |
C2 | 0.7239 (3) | 0.9574 (3) | 0.55753 (18) | 0.0443 (7) | |
H2A | 0.7536 | 0.9567 | 0.5026 | 0.053* | |
H2B | 0.6670 | 1.0393 | 0.5553 | 0.053* | |
C3 | 0.8848 (3) | 1.0338 (3) | 0.61055 (18) | 0.0438 (7) | |
H3A | 0.8138 | 1.1096 | 0.6006 | 0.053* | |
H3B | 0.9443 | 1.0423 | 0.5662 | 0.053* | |
C4 | 0.9526 (3) | 1.0095 (3) | 0.69153 (18) | 0.0381 (6) | |
C5 | 1.0036 (3) | 0.9358 (3) | 0.82128 (19) | 0.0393 (7) | |
C6 | 1.0163 (3) | 0.8747 (3) | 0.9047 (2) | 0.0497 (8) | |
H6 | 0.9621 | 0.8275 | 0.9291 | 0.060* | |
C7 | 1.1123 (4) | 0.8869 (3) | 0.9498 (2) | 0.0589 (9) | |
H7 | 1.1221 | 0.8480 | 1.0059 | 0.071* | |
C8 | 1.1956 (4) | 0.9562 (3) | 0.9138 (3) | 0.0608 (10) | |
H8 | 1.2601 | 0.9612 | 0.9462 | 0.073* | |
C9 | 1.1842 (3) | 1.0169 (3) | 0.8315 (2) | 0.0520 (8) | |
H9 | 1.2397 | 1.0628 | 0.8074 | 0.062* | |
C10 | 1.0864 (3) | 1.0070 (3) | 0.7856 (2) | 0.0423 (7) | |
C11 | 0.9413 (3) | 0.8190 (3) | 0.60412 (19) | 0.0434 (7) | |
H11A | 0.9297 | 0.8057 | 0.5510 | 0.052* | |
H11B | 1.0239 | 0.8355 | 0.6054 | 0.052* | |
C12 | 0.9414 (3) | 0.7065 (3) | 0.67009 (19) | 0.0404 (7) | |
C13 | 0.9106 (3) | 0.5870 (3) | 0.7870 (2) | 0.0439 (7) | |
C14 | 0.8774 (4) | 0.5367 (3) | 0.8664 (2) | 0.0524 (8) | |
H14 | 0.8228 | 0.5856 | 0.8962 | 0.063* | |
C15 | 0.9291 (4) | 0.4106 (4) | 0.8990 (3) | 0.0700 (11) | |
H15 | 0.9104 | 0.3742 | 0.9525 | 0.084* | |
C16 | 1.0083 (4) | 0.3365 (4) | 0.8539 (3) | 0.0775 (13) | |
H16 | 1.0393 | 0.2517 | 0.8776 | 0.093* | |
C17 | 1.0417 (4) | 0.3846 (4) | 0.7761 (3) | 0.0730 (12) | |
H17 | 1.0950 | 0.3346 | 0.7465 | 0.088* | |
C18 | 0.9927 (3) | 0.5121 (3) | 0.7428 (2) | 0.0527 (8) | |
C19 | 0.4865 (3) | 0.9738 (3) | 0.6662 (2) | 0.0440 (7) | |
H19A | 0.4238 | 0.9478 | 0.7042 | 0.053* | |
H19B | 0.4474 | 1.0029 | 0.6110 | 0.053* | |
C20 | 0.5218 (3) | 1.0769 (3) | 0.68755 (18) | 0.0386 (7) | |
C21 | 0.5050 (3) | 1.2598 (3) | 0.70313 (19) | 0.0451 (7) | |
C22 | 0.4686 (4) | 1.3832 (3) | 0.7052 (2) | 0.0587 (9) | |
H22 | 0.3867 | 1.4360 | 0.6869 | 0.070* | |
C23 | 0.5591 (4) | 1.4227 (3) | 0.7353 (3) | 0.0648 (11) | |
H23 | 0.5379 | 1.5045 | 0.7375 | 0.078* | |
C24 | 0.6816 (4) | 1.3445 (4) | 0.7628 (2) | 0.0622 (10) | |
H24 | 0.7403 | 1.3752 | 0.7828 | 0.075* | |
C25 | 0.7183 (4) | 1.2220 (3) | 0.7612 (2) | 0.0498 (8) | |
H25 | 0.8004 | 1.1699 | 0.7799 | 0.060* | |
C26 | 0.6285 (3) | 1.1797 (3) | 0.73060 (18) | 0.0403 (7) | |
C27 | 0.5784 (3) | 0.7514 (3) | 0.72125 (18) | 0.0406 (7) | |
H27A | 0.6449 | 0.6793 | 0.7140 | 0.049* | |
H27B | 0.4950 | 0.7469 | 0.7058 | 0.049* | |
C28 | 0.5802 (3) | 0.7576 (3) | 0.80841 (18) | 0.0380 (6) | |
C29 | 0.5324 (3) | 0.7414 (3) | 0.9378 (2) | 0.0477 (8) | |
C30 | 0.4836 (4) | 0.7203 (4) | 1.0160 (2) | 0.0644 (10) | |
H30 | 0.4234 | 0.6762 | 1.0302 | 0.077* | |
C31 | 0.5272 (5) | 0.7664 (5) | 1.0710 (2) | 0.0750 (12) | |
H31 | 0.4957 | 0.7543 | 1.1238 | 0.090* | |
C32 | 0.6186 (5) | 0.8317 (4) | 1.0501 (2) | 0.0728 (12) | |
H32 | 0.6461 | 0.8619 | 1.0895 | 0.087* | |
C33 | 0.6691 (4) | 0.8527 (4) | 0.9729 (2) | 0.0560 (9) | |
H33 | 0.7302 | 0.8960 | 0.9594 | 0.067* | |
C34 | 0.6239 (3) | 0.8058 (3) | 0.91627 (18) | 0.0395 (7) | |
C35 | 0.2331 (6) | 0.5681 (6) | 0.8657 (5) | 0.122 (2) | |
H35A | 0.2554 | 0.5382 | 0.9235 | 0.182* | |
H35B | 0.2409 | 0.4992 | 0.8434 | 0.182* | |
H35C | 0.1456 | 0.6209 | 0.8574 | 0.182* | |
C36 | 0.4998 (6) | 0.6466 (4) | 0.5199 (3) | 0.1029 (18) | |
H36A | 0.5832 | 0.6546 | 0.5022 | 0.154* | |
H36B | 0.4745 | 0.5954 | 0.4919 | 0.154* | |
H36C | 0.5041 | 0.6096 | 0.5782 | 0.154* | |
Cl1 | 0.81962 (8) | 0.76367 (8) | 0.41547 (5) | 0.0523 (2) | |
Cl2 | 0.25611 (11) | 0.79632 (15) | 0.65016 (9) | 0.0972 (4) | |
N1 | 0.8357 (2) | 0.9273 (2) | 0.61481 (14) | 0.0388 (6) | |
N2 | 0.6035 (2) | 0.8669 (2) | 0.67068 (15) | 0.0370 (5) | |
N3 | 0.9191 (2) | 0.9405 (2) | 0.75989 (15) | 0.0378 (5) | |
N4 | 1.0494 (3) | 1.0531 (2) | 0.70377 (16) | 0.0446 (6) | |
H4 | 1.0824 | 1.1013 | 0.6671 | 0.053* | |
N5 | 0.8790 (2) | 0.7102 (2) | 0.73796 (15) | 0.0389 (6) | |
N6 | 1.0092 (3) | 0.5910 (3) | 0.66900 (18) | 0.0526 (7) | |
H6A | 1.0546 | 0.5701 | 0.6293 | 0.063* | |
N7 | 0.6534 (2) | 0.8140 (2) | 0.83407 (15) | 0.0386 (6) | |
N8 | 0.5074 (3) | 0.7112 (3) | 0.86743 (16) | 0.0488 (7) | |
H8A | 0.4552 | 0.6703 | 0.8626 | 0.059* | |
N12 | 0.4403 (3) | 1.1903 (2) | 0.67747 (16) | 0.0459 (6) | |
H12 | 0.3618 | 1.2153 | 0.6584 | 0.055* | |
N13 | 0.6354 (2) | 1.0632 (2) | 0.71968 (15) | 0.0398 (6) | |
O1 | 0.3132 (4) | 0.6324 (5) | 0.8274 (3) | 0.1190 (14) | |
H1 | 0.2816 | 0.6754 | 0.7820 | 0.178* | |
O2 | 0.4147 (6) | 0.7566 (4) | 0.5025 (3) | 0.154 (2) | |
H2 | 0.3433 | 0.7497 | 0.5171 | 0.231* | |
O3 | 0.1666 (6) | 0.5150 (6) | 0.5485 (3) | 0.100 (3) | 0.752 (18) |
H3 | 0.1713 | 0.4426 | 0.5524 | 0.150* | 0.752 (18) |
C37 | 0.1726 (9) | 0.5770 (9) | 0.4660 (4) | 0.101 (3) | 0.752 (18) |
H37A | 0.1762 | 0.6592 | 0.4620 | 0.152* | 0.752 (18) |
H37B | 0.0972 | 0.5814 | 0.4361 | 0.152* | 0.752 (18) |
H37C | 0.2486 | 0.5331 | 0.4432 | 0.152* | 0.752 (18) |
C37' | 0.143 (10) | 0.581 (10) | 0.460 (4) | 0.37 (6) | 0.248 (18) |
H37D | 0.0541 | 0.6280 | 0.4461 | 0.558* | 0.248 (18) |
H37E | 0.1533 | 0.4957 | 0.4632 | 0.558* | 0.248 (18) |
H37F | 0.1965 | 0.6126 | 0.4176 | 0.558* | 0.248 (18) |
O3' | 0.178 (3) | 0.591 (4) | 0.5330 (19) | 0.155 (11) | 0.248 (18) |
H3' | 0.2517 | 0.5977 | 0.5310 | 0.232* | 0.248 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0340 (2) | 0.0360 (2) | 0.0319 (2) | −0.01547 (16) | 0.00156 (14) | −0.00855 (15) |
C1 | 0.0439 (18) | 0.0517 (18) | 0.0352 (15) | −0.0184 (15) | −0.0050 (13) | −0.0149 (13) |
C2 | 0.0507 (19) | 0.0497 (18) | 0.0316 (15) | −0.0177 (15) | −0.0015 (13) | −0.0055 (13) |
C3 | 0.0516 (19) | 0.0449 (17) | 0.0365 (16) | −0.0236 (15) | 0.0040 (13) | −0.0033 (13) |
C4 | 0.0415 (17) | 0.0378 (15) | 0.0390 (15) | −0.0174 (13) | 0.0052 (13) | −0.0111 (12) |
C5 | 0.0374 (16) | 0.0394 (16) | 0.0434 (16) | −0.0110 (13) | 0.0013 (13) | −0.0150 (13) |
C6 | 0.053 (2) | 0.0480 (18) | 0.0473 (18) | −0.0194 (16) | −0.0051 (15) | −0.0050 (15) |
C7 | 0.067 (2) | 0.060 (2) | 0.051 (2) | −0.0205 (19) | −0.0133 (17) | −0.0106 (17) |
C8 | 0.055 (2) | 0.056 (2) | 0.075 (3) | −0.0177 (18) | −0.0210 (19) | −0.0204 (19) |
C9 | 0.048 (2) | 0.052 (2) | 0.066 (2) | −0.0231 (16) | 0.0001 (16) | −0.0220 (17) |
C10 | 0.0417 (18) | 0.0412 (17) | 0.0496 (18) | −0.0157 (14) | 0.0017 (14) | −0.0174 (14) |
C11 | 0.0413 (18) | 0.0512 (18) | 0.0395 (16) | −0.0166 (15) | 0.0069 (13) | −0.0126 (14) |
C12 | 0.0366 (16) | 0.0449 (17) | 0.0421 (16) | −0.0121 (13) | −0.0003 (13) | −0.0150 (13) |
C13 | 0.0414 (18) | 0.0388 (16) | 0.0492 (18) | −0.0098 (14) | −0.0053 (14) | −0.0090 (14) |
C14 | 0.058 (2) | 0.0445 (18) | 0.0509 (19) | −0.0137 (16) | 0.0015 (16) | −0.0069 (15) |
C15 | 0.085 (3) | 0.050 (2) | 0.063 (2) | −0.016 (2) | 0.002 (2) | −0.0002 (18) |
C16 | 0.078 (3) | 0.039 (2) | 0.094 (3) | −0.001 (2) | −0.001 (2) | 0.001 (2) |
C17 | 0.074 (3) | 0.045 (2) | 0.090 (3) | −0.0027 (19) | 0.007 (2) | −0.019 (2) |
C18 | 0.048 (2) | 0.0436 (18) | 0.063 (2) | −0.0085 (15) | 0.0007 (16) | −0.0139 (16) |
C19 | 0.0342 (16) | 0.0456 (17) | 0.0534 (18) | −0.0120 (14) | −0.0042 (14) | −0.0139 (14) |
C20 | 0.0401 (17) | 0.0357 (15) | 0.0386 (15) | −0.0098 (13) | −0.0001 (13) | −0.0090 (12) |
C21 | 0.056 (2) | 0.0414 (17) | 0.0386 (16) | −0.0147 (15) | 0.0066 (14) | −0.0127 (13) |
C22 | 0.069 (2) | 0.0436 (19) | 0.059 (2) | −0.0122 (18) | 0.0079 (18) | −0.0116 (16) |
C23 | 0.087 (3) | 0.0391 (19) | 0.077 (3) | −0.027 (2) | 0.019 (2) | −0.0237 (18) |
C24 | 0.077 (3) | 0.060 (2) | 0.069 (2) | −0.040 (2) | 0.016 (2) | −0.0294 (19) |
C25 | 0.053 (2) | 0.0531 (19) | 0.054 (2) | −0.0251 (16) | 0.0080 (16) | −0.0231 (16) |
C26 | 0.0471 (18) | 0.0413 (16) | 0.0365 (15) | −0.0190 (14) | 0.0071 (13) | −0.0110 (13) |
C27 | 0.0408 (17) | 0.0426 (17) | 0.0451 (17) | −0.0209 (14) | 0.0008 (13) | −0.0132 (13) |
C28 | 0.0386 (16) | 0.0396 (16) | 0.0390 (15) | −0.0176 (13) | 0.0011 (12) | −0.0087 (12) |
C29 | 0.0470 (19) | 0.055 (2) | 0.0418 (17) | −0.0215 (16) | 0.0020 (14) | −0.0073 (14) |
C30 | 0.069 (3) | 0.085 (3) | 0.048 (2) | −0.042 (2) | 0.0133 (18) | −0.0127 (19) |
C31 | 0.085 (3) | 0.110 (4) | 0.041 (2) | −0.048 (3) | 0.0204 (19) | −0.020 (2) |
C32 | 0.091 (3) | 0.101 (3) | 0.046 (2) | −0.046 (3) | 0.014 (2) | −0.033 (2) |
C33 | 0.067 (2) | 0.068 (2) | 0.0444 (18) | −0.033 (2) | 0.0078 (16) | −0.0209 (17) |
C34 | 0.0386 (16) | 0.0450 (17) | 0.0369 (15) | −0.0174 (14) | 0.0042 (12) | −0.0089 (13) |
C35 | 0.095 (4) | 0.121 (5) | 0.173 (7) | −0.059 (4) | 0.020 (4) | −0.051 (4) |
C36 | 0.152 (6) | 0.059 (3) | 0.088 (4) | −0.021 (3) | 0.011 (3) | −0.015 (3) |
Cl1 | 0.0505 (5) | 0.0553 (5) | 0.0541 (5) | −0.0238 (4) | 0.0026 (4) | −0.0107 (4) |
Cl2 | 0.0509 (6) | 0.1369 (12) | 0.1111 (10) | −0.0283 (7) | 0.0003 (6) | −0.0437 (9) |
N1 | 0.0427 (14) | 0.0419 (14) | 0.0340 (12) | −0.0185 (12) | 0.0018 (10) | −0.0073 (10) |
N2 | 0.0406 (14) | 0.0362 (13) | 0.0367 (13) | −0.0140 (11) | −0.0014 (10) | −0.0104 (10) |
N3 | 0.0361 (13) | 0.0414 (13) | 0.0370 (13) | −0.0161 (11) | −0.0012 (10) | −0.0066 (10) |
N4 | 0.0454 (15) | 0.0476 (15) | 0.0484 (15) | −0.0258 (13) | 0.0095 (12) | −0.0135 (12) |
N5 | 0.0383 (14) | 0.0405 (14) | 0.0377 (13) | −0.0118 (11) | 0.0009 (10) | −0.0097 (11) |
N6 | 0.0523 (17) | 0.0521 (17) | 0.0561 (17) | −0.0130 (14) | 0.0134 (13) | −0.0233 (14) |
N7 | 0.0419 (14) | 0.0426 (14) | 0.0370 (13) | −0.0196 (12) | 0.0048 (11) | −0.0127 (11) |
N8 | 0.0504 (16) | 0.0591 (17) | 0.0459 (15) | −0.0334 (14) | 0.0044 (12) | −0.0106 (13) |
N12 | 0.0435 (15) | 0.0448 (15) | 0.0465 (15) | −0.0085 (12) | −0.0026 (12) | −0.0116 (12) |
N13 | 0.0432 (15) | 0.0384 (13) | 0.0419 (14) | −0.0158 (11) | 0.0016 (11) | −0.0136 (11) |
O1 | 0.098 (3) | 0.168 (4) | 0.120 (3) | −0.091 (3) | −0.016 (2) | −0.026 (3) |
O2 | 0.187 (5) | 0.101 (3) | 0.107 (3) | 0.023 (3) | 0.025 (3) | 0.009 (2) |
O3 | 0.135 (4) | 0.065 (3) | 0.105 (4) | −0.028 (3) | 0.051 (3) | −0.039 (3) |
C37 | 0.082 (5) | 0.094 (5) | 0.094 (5) | −0.002 (4) | 0.015 (4) | 0.003 (4) |
C37' | 0.37 (6) | 0.37 (6) | 0.37 (6) | −0.11 (2) | 0.009 (11) | −0.098 (19) |
O3' | 0.158 (13) | 0.151 (15) | 0.163 (14) | −0.052 (9) | 0.017 (9) | −0.049 (10) |
Ni1—N5 | 2.076 (2) | C21—N12 | 1.375 (4) |
Ni1—N3 | 2.078 (2) | C21—C22 | 1.394 (5) |
Ni1—N13 | 2.082 (2) | C21—C26 | 1.403 (5) |
Ni1—N7 | 2.097 (2) | C22—C23 | 1.367 (6) |
Ni1—N1 | 2.167 (2) | C22—H22 | 0.9300 |
Ni1—N2 | 2.175 (2) | C23—C24 | 1.389 (6) |
C1—N2 | 1.476 (4) | C23—H23 | 0.9300 |
C1—C2 | 1.528 (4) | C24—C25 | 1.382 (5) |
C1—H1A | 0.9700 | C24—H24 | 0.9300 |
C1—H1B | 0.9700 | C25—C26 | 1.385 (4) |
C2—N1 | 1.481 (4) | C25—H25 | 0.9300 |
C2—H2A | 0.9700 | C26—N13 | 1.408 (4) |
C2—H2B | 0.9700 | C27—N2 | 1.485 (4) |
C3—N1 | 1.476 (4) | C27—C28 | 1.494 (4) |
C3—C4 | 1.498 (4) | C27—H27A | 0.9700 |
C3—H3A | 0.9700 | C27—H27B | 0.9700 |
C3—H3B | 0.9700 | C28—N7 | 1.320 (4) |
C4—N3 | 1.321 (4) | C28—N8 | 1.340 (4) |
C4—N4 | 1.339 (4) | C29—C30 | 1.386 (5) |
C5—C6 | 1.389 (4) | C29—N8 | 1.386 (4) |
C5—N3 | 1.391 (4) | C29—C34 | 1.392 (4) |
C5—C10 | 1.406 (4) | C30—C31 | 1.354 (6) |
C6—C7 | 1.377 (5) | C30—H30 | 0.9300 |
C6—H6 | 0.9300 | C31—C32 | 1.397 (6) |
C7—C8 | 1.397 (5) | C31—H31 | 0.9300 |
C7—H7 | 0.9300 | C32—C33 | 1.378 (5) |
C8—C9 | 1.372 (5) | C32—H32 | 0.9300 |
C8—H8 | 0.9300 | C33—C34 | 1.393 (5) |
C9—C10 | 1.387 (5) | C33—H33 | 0.9300 |
C9—H9 | 0.9300 | C34—N7 | 1.394 (4) |
C10—N4 | 1.371 (4) | C35—O1 | 1.344 (6) |
C11—C12 | 1.478 (4) | C35—H35A | 0.9600 |
C11—N1 | 1.488 (4) | C35—H35B | 0.9600 |
C11—H11A | 0.9700 | C35—H35C | 0.9600 |
C11—H11B | 0.9700 | C36—O2 | 1.313 (6) |
C12—N5 | 1.309 (4) | C36—H36A | 0.9600 |
C12—N6 | 1.345 (4) | C36—H36B | 0.9600 |
C13—C14 | 1.388 (5) | C36—H36C | 0.9600 |
C13—C18 | 1.400 (5) | N4—H4 | 0.8600 |
C13—N5 | 1.407 (4) | N6—H6A | 0.8600 |
C14—C15 | 1.381 (5) | N8—H8A | 0.8600 |
C14—H14 | 0.9300 | N12—H12 | 0.8600 |
C15—C16 | 1.390 (6) | O1—H1 | 0.8200 |
C15—H15 | 0.9300 | O2—H2 | 0.8200 |
C16—C17 | 1.360 (6) | O3—C37 | 1.395 (7) |
C16—H16 | 0.9300 | O3—H3 | 0.8200 |
C17—C18 | 1.393 (5) | C37—H37A | 0.9600 |
C17—H17 | 0.9300 | C37—H37B | 0.9600 |
C18—N6 | 1.376 (4) | C37—H37C | 0.9600 |
C19—N2 | 1.488 (4) | C37'—O3' | 1.358 (9) |
C19—C20 | 1.502 (4) | C37'—H37D | 0.9600 |
C19—H19A | 0.9700 | C37'—H37E | 0.9600 |
C19—H19B | 0.9700 | C37'—H37F | 0.9600 |
C20—N13 | 1.314 (4) | O3'—H3' | 0.8200 |
C20—N12 | 1.335 (4) | ||
N5—Ni1—N3 | 91.55 (10) | C22—C23—C24 | 122.0 (3) |
N5—Ni1—N13 | 171.99 (10) | C22—C23—H23 | 119.0 |
N3—Ni1—N13 | 92.50 (10) | C24—C23—H23 | 119.0 |
N5—Ni1—N7 | 92.35 (10) | C25—C24—C23 | 121.6 (4) |
N3—Ni1—N7 | 120.95 (10) | C25—C24—H24 | 119.2 |
N13—Ni1—N7 | 91.49 (10) | C23—C24—H24 | 119.2 |
N5—Ni1—N1 | 80.72 (9) | C24—C25—C26 | 117.5 (4) |
N3—Ni1—N1 | 79.15 (9) | C24—C25—H25 | 121.2 |
N13—Ni1—N1 | 93.27 (9) | C26—C25—H25 | 121.2 |
N7—Ni1—N1 | 159.13 (10) | C25—C26—C21 | 120.3 (3) |
N5—Ni1—N2 | 93.07 (9) | C25—C26—N13 | 131.7 (3) |
N3—Ni1—N2 | 159.90 (9) | C21—C26—N13 | 108.0 (3) |
N13—Ni1—N2 | 80.83 (9) | N2—C27—C28 | 105.7 (2) |
N7—Ni1—N2 | 78.41 (9) | N2—C27—H27A | 110.6 |
N1—Ni1—N2 | 82.31 (9) | C28—C27—H27A | 110.6 |
N2—C1—C2 | 108.7 (2) | N2—C27—H27B | 110.6 |
N2—C1—H1A | 110.0 | C28—C27—H27B | 110.6 |
C2—C1—H1A | 110.0 | H27A—C27—H27B | 108.7 |
N2—C1—H1B | 110.0 | N7—C28—N8 | 113.1 (3) |
C2—C1—H1B | 110.0 | N7—C28—C27 | 122.0 (3) |
H1A—C1—H1B | 108.3 | N8—C28—C27 | 124.9 (3) |
N1—C2—C1 | 108.6 (2) | C30—C29—N8 | 132.6 (3) |
N1—C2—H2A | 110.0 | C30—C29—C34 | 121.8 (3) |
C1—C2—H2A | 110.0 | N8—C29—C34 | 105.6 (3) |
N1—C2—H2B | 110.0 | C31—C30—C29 | 117.4 (4) |
C1—C2—H2B | 110.0 | C31—C30—H30 | 121.3 |
H2A—C2—H2B | 108.3 | C29—C30—H30 | 121.3 |
N1—C3—C4 | 107.2 (2) | C30—C31—C32 | 121.4 (3) |
N1—C3—H3A | 110.3 | C30—C31—H31 | 119.3 |
C4—C3—H3A | 110.3 | C32—C31—H31 | 119.3 |
N1—C3—H3B | 110.3 | C33—C32—C31 | 122.2 (4) |
C4—C3—H3B | 110.3 | C33—C32—H32 | 118.9 |
H3A—C3—H3B | 108.5 | C31—C32—H32 | 118.9 |
N3—C4—N4 | 113.0 (3) | C32—C33—C34 | 116.4 (3) |
N3—C4—C3 | 121.3 (3) | C32—C33—H33 | 121.8 |
N4—C4—C3 | 125.7 (3) | C34—C33—H33 | 121.8 |
C6—C5—N3 | 131.2 (3) | C29—C34—C33 | 120.8 (3) |
C6—C5—C10 | 120.4 (3) | C29—C34—N7 | 109.1 (3) |
N3—C5—C10 | 108.3 (3) | C33—C34—N7 | 130.1 (3) |
C7—C6—C5 | 117.3 (3) | O1—C35—H35A | 109.5 |
C7—C6—H6 | 121.3 | O1—C35—H35B | 109.5 |
C5—C6—H6 | 121.3 | H35A—C35—H35B | 109.5 |
C6—C7—C8 | 122.0 (3) | O1—C35—H35C | 109.5 |
C6—C7—H7 | 119.0 | H35A—C35—H35C | 109.5 |
C8—C7—H7 | 119.0 | H35B—C35—H35C | 109.5 |
C9—C8—C7 | 121.3 (3) | O2—C36—H36A | 109.5 |
C9—C8—H8 | 119.4 | O2—C36—H36B | 109.5 |
C7—C8—H8 | 119.4 | H36A—C36—H36B | 109.5 |
C8—C9—C10 | 117.3 (3) | O2—C36—H36C | 109.5 |
C8—C9—H9 | 121.4 | H36A—C36—H36C | 109.5 |
C10—C9—H9 | 121.4 | H36B—C36—H36C | 109.5 |
N4—C10—C9 | 132.5 (3) | C3—N1—C2 | 113.5 (2) |
N4—C10—C5 | 105.8 (3) | C3—N1—C11 | 111.1 (2) |
C9—C10—C5 | 121.7 (3) | C2—N1—C11 | 111.7 (2) |
C12—C11—N1 | 110.6 (2) | C3—N1—Ni1 | 104.52 (17) |
C12—C11—H11A | 109.5 | C2—N1—Ni1 | 105.47 (18) |
N1—C11—H11A | 109.5 | C11—N1—Ni1 | 110.16 (17) |
C12—C11—H11B | 109.5 | C1—N2—C27 | 114.3 (2) |
N1—C11—H11B | 109.5 | C1—N2—C19 | 111.8 (2) |
H11A—C11—H11B | 108.1 | C27—N2—C19 | 109.8 (2) |
N5—C12—N6 | 112.8 (3) | C1—N2—Ni1 | 106.06 (18) |
N5—C12—C11 | 122.9 (3) | C27—N2—Ni1 | 104.33 (17) |
N6—C12—C11 | 124.3 (3) | C19—N2—Ni1 | 110.27 (17) |
C14—C13—C18 | 120.8 (3) | C4—N3—C5 | 105.3 (2) |
C14—C13—N5 | 131.1 (3) | C4—N3—Ni1 | 110.72 (19) |
C18—C13—N5 | 108.0 (3) | C5—N3—Ni1 | 143.9 (2) |
C15—C14—C13 | 116.9 (3) | C4—N4—C10 | 107.4 (2) |
C15—C14—H14 | 121.5 | C4—N4—H4 | 126.3 |
C13—C14—H14 | 121.5 | C10—N4—H4 | 126.3 |
C14—C15—C16 | 121.8 (4) | C12—N5—C13 | 105.7 (3) |
C14—C15—H15 | 119.1 | C12—N5—Ni1 | 113.6 (2) |
C16—C15—H15 | 119.1 | C13—N5—Ni1 | 140.5 (2) |
C17—C16—C15 | 121.9 (4) | C12—N6—C18 | 107.6 (3) |
C17—C16—H16 | 119.1 | C12—N6—H6A | 126.2 |
C15—C16—H16 | 119.1 | C18—N6—H6A | 126.2 |
C16—C17—C18 | 117.2 (4) | C28—N7—C34 | 105.1 (2) |
C16—C17—H17 | 121.4 | C28—N7—Ni1 | 110.24 (19) |
C18—C17—H17 | 121.4 | C34—N7—Ni1 | 144.6 (2) |
N6—C18—C17 | 132.8 (4) | C28—N8—C29 | 107.1 (3) |
N6—C18—C13 | 105.8 (3) | C28—N8—H8A | 126.4 |
C17—C18—C13 | 121.3 (4) | C29—N8—H8A | 126.4 |
N2—C19—C20 | 110.3 (2) | C20—N12—C21 | 107.5 (3) |
N2—C19—H19A | 109.6 | C20—N12—H12 | 126.3 |
C20—C19—H19A | 109.6 | C21—N12—H12 | 126.3 |
N2—C19—H19B | 109.6 | C20—N13—C26 | 105.1 (3) |
C20—C19—H19B | 109.6 | C20—N13—Ni1 | 113.40 (19) |
H19A—C19—H19B | 108.1 | C26—N13—Ni1 | 141.5 (2) |
N13—C20—N12 | 113.5 (3) | C35—O1—H1 | 109.5 |
N13—C20—C19 | 123.1 (3) | C36—O2—H2 | 109.5 |
N12—C20—C19 | 123.4 (3) | O3'—C37'—H37D | 109.5 |
N12—C21—C22 | 132.3 (3) | O3'—C37'—H37E | 109.5 |
N12—C21—C26 | 105.9 (3) | H37D—C37'—H37E | 109.5 |
C22—C21—C26 | 121.8 (3) | O3'—C37'—H37F | 109.5 |
C23—C22—C21 | 116.8 (4) | H37D—C37'—H37F | 109.5 |
C23—C22—H22 | 121.6 | H37E—C37'—H37F | 109.5 |
C21—C22—H22 | 121.6 | C37'—O3'—H3' | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···Cl1i | 0.82 | 2.30 | 3.117 (7) | 171 |
N4—H4···Cl1ii | 0.86 | 2.29 | 3.140 (3) | 172 |
N6—H6A···O3iii | 0.86 | 1.90 | 2.761 (5) | 175 |
N12—H12···Cl1iv | 0.86 | 2.29 | 3.116 (3) | 162 |
C2—H2B···O2iv | 0.97 | 2.25 | 3.145 (5) | 154 |
C11—H11B···Cl2iii | 0.97 | 2.53 | 3.445 (3) | 157 |
O1—H1···Cl2 | 0.82 | 2.27 | 3.065 (4) | 163 |
O2—H2···Cl2 | 0.82 | 2.53 | 3.027 (5) | 120 |
N8—H8A···O1 | 0.86 | 1.88 | 2.705 (4) | 161 |
C27—H27B···Cl2 | 0.97 | 2.64 | 3.582 (3) | 165 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+2, −z+1; (iii) x+1, y, z; (iv) −x+1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C34H32N10)]Cl2·3CH4O |
Mr | 806.43 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 10.8183 (5), 11.7267 (6), 16.8837 (8) |
α, β, γ (°) | 74.312 (1), 87.491 (1), 73.065 (1) |
V (Å3) | 1971.28 (16) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.68 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17041, 7670, 6229 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.145, 1.05 |
No. of reflections | 7670 |
No. of parameters | 505 |
No. of restraints | 26 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.52, −0.50 |
Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.
Ni1—N5 | 2.076 (2) | Ni1—N7 | 2.097 (2) |
Ni1—N3 | 2.078 (2) | Ni1—N1 | 2.167 (2) |
Ni1—N13 | 2.082 (2) | Ni1—N2 | 2.175 (2) |
N5—Ni1—N3 | 91.55 (10) | N13—Ni1—N1 | 93.27 (9) |
N5—Ni1—N13 | 171.99 (10) | N7—Ni1—N1 | 159.13 (10) |
N3—Ni1—N13 | 92.50 (10) | N5—Ni1—N2 | 93.07 (9) |
N5—Ni1—N7 | 92.35 (10) | N3—Ni1—N2 | 159.90 (9) |
N3—Ni1—N7 | 120.95 (10) | N13—Ni1—N2 | 80.83 (9) |
N13—Ni1—N7 | 91.49 (10) | N7—Ni1—N2 | 78.41 (9) |
N5—Ni1—N1 | 80.72 (9) | N1—Ni1—N2 | 82.31 (9) |
N3—Ni1—N1 | 79.15 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···Cl1i | 0.82 | 2.30 | 3.117 (7) | 171.2 |
N4—H4···Cl1ii | 0.86 | 2.29 | 3.140 (3) | 172.0 |
N6—H6A···O3iii | 0.86 | 1.90 | 2.761 (5) | 175.1 |
N12—H12···Cl1iv | 0.86 | 2.29 | 3.116 (3) | 161.6 |
C2—H2B···O2iv | 0.97 | 2.25 | 3.145 (5) | 153.7 |
C11—H11B···Cl2iii | 0.97 | 2.53 | 3.445 (3) | 157.2 |
O1—H1···Cl2 | 0.82 | 2.27 | 3.065 (4) | 162.8 |
O2—H2···Cl2 | 0.82 | 2.53 | 3.027 (5) | 120.0 |
N8—H8A···O1 | 0.86 | 1.88 | 2.705 (4) | 160.8 |
C27—H27B···Cl2 | 0.97 | 2.64 | 3.582 (3) | 165.4 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+2, −z+1; (iii) x+1, y, z; (iv) −x+1, −y+2, −z+1. |
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Recently, study in the ligands containing-polybenzimidazoles and their metal coordination compounds has been widely carried on (Chen et al., 2004; Liao et al., 2001). As the continuing work of our workgroup, we report the crystallography structure of the title compound, [Ni(EDTB)]2Cl-.3CH3OH, (I); {EDTB = N,N,N',N'-tetrakis(2'-benzimidazolyl methyl)-1,2-ethanediamine}.
In the title molecular structure (I), NiII is coordinated by four four benzimidazole nitrogen atoms, two amino N atoms of EDTB, forming a distorted octahedron coordination geometry (Table 1 and Fig. 1).
In the supramolecular structure, there are a number of N(or O)–H···Cl, N–H···O and O–H···N hydrogen bonding interactions which link the molecules into a three-dimensional framwork (Table 2 and Fig.2.).