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In the title compound, [Ni(C34H32N10)]Cl2·3CH4O, the NiII atom is in a distorted octa­hedral coordination environment. In the crystal structure, extensive hydrogen bonding links the ions and mol­ecules into a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020879/at2277sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020879/at2277Isup2.hkl
Contains datablock I

CCDC reference: 650524

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Comment top

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.).

Related literature top

For related literature, see: Chen et al. (2004); Hendriks et al. (1982); Liao et al. (2001).

Experimental top

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.

Refinement top

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).

Structure description top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. View of the molecular structure of (I), showing 30% probability displacement ellipsoids. Only the major disorder component is shown.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing hydrogen bonds as dashed lines.
[N,N,N',N'-Tetrakis(benzimidazol-2-ylmethyl)ethane-1,2-diamine]nickel(II) dichloride trimethanol solvate top
Crystal data top
[Ni(C34H32N10)]Cl2·3CH4OZ = 2
Mr = 806.43F(000) = 844
Triclinic, P1Dx = 1.359 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.8183 (5) ÅCell parameters from 5644 reflections
b = 11.7267 (6) Åθ = 0.0–0.0°
c = 16.8837 (8) ŵ = 0.68 mm1
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
Data collection top
Bruker SMART CCD area-detector
diffractometer
6229 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 26.0°, θmin = 1.9°
φ and ω scansh = 1312
17041 measured reflectionsk = 1414
7670 independent reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H 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 parametersΔρmax = 0.52 e Å3
26 restraintsΔρmin = 0.50 e Å3
Crystal data top
[Ni(C34H32N10)]Cl2·3CH4Oγ = 73.065 (1)°
Mr = 806.43V = 1971.28 (16) Å3
Triclinic, P1Z = 2
a = 10.8183 (5) ÅMo Kα radiation
b = 11.7267 (6) ŵ = 0.68 mm1
c = 16.8837 (8) ÅT = 298 K
α = 74.312 (1)°0.30 × 0.20 × 0.20 mm
β = 87.491 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
6229 reflections with I > 2σ(I)
17041 measured reflectionsRint = 0.031
7670 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05226 restraints
wR(F2) = 0.145H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.52 e Å3
7670 reflectionsΔρmin = 0.50 e Å3
505 parameters
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
xyzUiso*/UeqOcc. (<1)
Ni10.76117 (3)0.88541 (3)0.73720 (2)0.03295 (13)
C10.6510 (3)0.8609 (3)0.58813 (18)0.0418 (7)
H1A0.57880.87750.55050.050*
H1B0.70810.77890.59090.050*
C20.7239 (3)0.9574 (3)0.55753 (18)0.0443 (7)
H2A0.75360.95670.50260.053*
H2B0.66701.03930.55530.053*
C30.8848 (3)1.0338 (3)0.61055 (18)0.0438 (7)
H3A0.81381.10960.60060.053*
H3B0.94431.04230.56620.053*
C40.9526 (3)1.0095 (3)0.69153 (18)0.0381 (6)
C51.0036 (3)0.9358 (3)0.82128 (19)0.0393 (7)
C61.0163 (3)0.8747 (3)0.9047 (2)0.0497 (8)
H60.96210.82750.92910.060*
C71.1123 (4)0.8869 (3)0.9498 (2)0.0589 (9)
H71.12210.84801.00590.071*
C81.1956 (4)0.9562 (3)0.9138 (3)0.0608 (10)
H81.26010.96120.94620.073*
C91.1842 (3)1.0169 (3)0.8315 (2)0.0520 (8)
H91.23971.06280.80740.062*
C101.0864 (3)1.0070 (3)0.7856 (2)0.0423 (7)
C110.9413 (3)0.8190 (3)0.60412 (19)0.0434 (7)
H11A0.92970.80570.55100.052*
H11B1.02390.83550.60540.052*
C120.9414 (3)0.7065 (3)0.67009 (19)0.0404 (7)
C130.9106 (3)0.5870 (3)0.7870 (2)0.0439 (7)
C140.8774 (4)0.5367 (3)0.8664 (2)0.0524 (8)
H140.82280.58560.89620.063*
C150.9291 (4)0.4106 (4)0.8990 (3)0.0700 (11)
H150.91040.37420.95250.084*
C161.0083 (4)0.3365 (4)0.8539 (3)0.0775 (13)
H161.03930.25170.87760.093*
C171.0417 (4)0.3846 (4)0.7761 (3)0.0730 (12)
H171.09500.33460.74650.088*
C180.9927 (3)0.5121 (3)0.7428 (2)0.0527 (8)
C190.4865 (3)0.9738 (3)0.6662 (2)0.0440 (7)
H19A0.42380.94780.70420.053*
H19B0.44741.00290.61100.053*
C200.5218 (3)1.0769 (3)0.68755 (18)0.0386 (7)
C210.5050 (3)1.2598 (3)0.70313 (19)0.0451 (7)
C220.4686 (4)1.3832 (3)0.7052 (2)0.0587 (9)
H220.38671.43600.68690.070*
C230.5591 (4)1.4227 (3)0.7353 (3)0.0648 (11)
H230.53791.50450.73750.078*
C240.6816 (4)1.3445 (4)0.7628 (2)0.0622 (10)
H240.74031.37520.78280.075*
C250.7183 (4)1.2220 (3)0.7612 (2)0.0498 (8)
H250.80041.16990.77990.060*
C260.6285 (3)1.1797 (3)0.73060 (18)0.0403 (7)
C270.5784 (3)0.7514 (3)0.72125 (18)0.0406 (7)
H27A0.64490.67930.71400.049*
H27B0.49500.74690.70580.049*
C280.5802 (3)0.7576 (3)0.80841 (18)0.0380 (6)
C290.5324 (3)0.7414 (3)0.9378 (2)0.0477 (8)
C300.4836 (4)0.7203 (4)1.0160 (2)0.0644 (10)
H300.42340.67621.03020.077*
C310.5272 (5)0.7664 (5)1.0710 (2)0.0750 (12)
H310.49570.75431.12380.090*
C320.6186 (5)0.8317 (4)1.0501 (2)0.0728 (12)
H320.64610.86191.08950.087*
C330.6691 (4)0.8527 (4)0.9729 (2)0.0560 (9)
H330.73020.89600.95940.067*
C340.6239 (3)0.8058 (3)0.91627 (18)0.0395 (7)
C350.2331 (6)0.5681 (6)0.8657 (5)0.122 (2)
H35A0.25540.53820.92350.182*
H35B0.24090.49920.84340.182*
H35C0.14560.62090.85740.182*
C360.4998 (6)0.6466 (4)0.5199 (3)0.1029 (18)
H36A0.58320.65460.50220.154*
H36B0.47450.59540.49190.154*
H36C0.50410.60960.57820.154*
Cl10.81962 (8)0.76367 (8)0.41547 (5)0.0523 (2)
Cl20.25611 (11)0.79632 (15)0.65016 (9)0.0972 (4)
N10.8357 (2)0.9273 (2)0.61481 (14)0.0388 (6)
N20.6035 (2)0.8669 (2)0.67068 (15)0.0370 (5)
N30.9191 (2)0.9405 (2)0.75989 (15)0.0378 (5)
N41.0494 (3)1.0531 (2)0.70377 (16)0.0446 (6)
H41.08241.10130.66710.053*
N50.8790 (2)0.7102 (2)0.73796 (15)0.0389 (6)
N61.0092 (3)0.5910 (3)0.66900 (18)0.0526 (7)
H6A1.05460.57010.62930.063*
N70.6534 (2)0.8140 (2)0.83407 (15)0.0386 (6)
N80.5074 (3)0.7112 (3)0.86743 (16)0.0488 (7)
H8A0.45520.67030.86260.059*
N120.4403 (3)1.1903 (2)0.67747 (16)0.0459 (6)
H120.36181.21530.65840.055*
N130.6354 (2)1.0632 (2)0.71968 (15)0.0398 (6)
O10.3132 (4)0.6324 (5)0.8274 (3)0.1190 (14)
H10.28160.67540.78200.178*
O20.4147 (6)0.7566 (4)0.5025 (3)0.154 (2)
H20.34330.74970.51710.231*
O30.1666 (6)0.5150 (6)0.5485 (3)0.100 (3)0.752 (18)
H30.17130.44260.55240.150*0.752 (18)
C370.1726 (9)0.5770 (9)0.4660 (4)0.101 (3)0.752 (18)
H37A0.17620.65920.46200.152*0.752 (18)
H37B0.09720.58140.43610.152*0.752 (18)
H37C0.24860.53310.44320.152*0.752 (18)
C37'0.143 (10)0.581 (10)0.460 (4)0.37 (6)0.248 (18)
H37D0.05410.62800.44610.558*0.248 (18)
H37E0.15330.49570.46320.558*0.248 (18)
H37F0.19650.61260.41760.558*0.248 (18)
O3'0.178 (3)0.591 (4)0.5330 (19)0.155 (11)0.248 (18)
H3'0.25170.59770.53100.232*0.248 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0340 (2)0.0360 (2)0.0319 (2)0.01547 (16)0.00156 (14)0.00855 (15)
C10.0439 (18)0.0517 (18)0.0352 (15)0.0184 (15)0.0050 (13)0.0149 (13)
C20.0507 (19)0.0497 (18)0.0316 (15)0.0177 (15)0.0015 (13)0.0055 (13)
C30.0516 (19)0.0449 (17)0.0365 (16)0.0236 (15)0.0040 (13)0.0033 (13)
C40.0415 (17)0.0378 (15)0.0390 (15)0.0174 (13)0.0052 (13)0.0111 (12)
C50.0374 (16)0.0394 (16)0.0434 (16)0.0110 (13)0.0013 (13)0.0150 (13)
C60.053 (2)0.0480 (18)0.0473 (18)0.0194 (16)0.0051 (15)0.0050 (15)
C70.067 (2)0.060 (2)0.051 (2)0.0205 (19)0.0133 (17)0.0106 (17)
C80.055 (2)0.056 (2)0.075 (3)0.0177 (18)0.0210 (19)0.0204 (19)
C90.048 (2)0.052 (2)0.066 (2)0.0231 (16)0.0001 (16)0.0220 (17)
C100.0417 (18)0.0412 (17)0.0496 (18)0.0157 (14)0.0017 (14)0.0174 (14)
C110.0413 (18)0.0512 (18)0.0395 (16)0.0166 (15)0.0069 (13)0.0126 (14)
C120.0366 (16)0.0449 (17)0.0421 (16)0.0121 (13)0.0003 (13)0.0150 (13)
C130.0414 (18)0.0388 (16)0.0492 (18)0.0098 (14)0.0053 (14)0.0090 (14)
C140.058 (2)0.0445 (18)0.0509 (19)0.0137 (16)0.0015 (16)0.0069 (15)
C150.085 (3)0.050 (2)0.063 (2)0.016 (2)0.002 (2)0.0002 (18)
C160.078 (3)0.039 (2)0.094 (3)0.001 (2)0.001 (2)0.001 (2)
C170.074 (3)0.045 (2)0.090 (3)0.0027 (19)0.007 (2)0.019 (2)
C180.048 (2)0.0436 (18)0.063 (2)0.0085 (15)0.0007 (16)0.0139 (16)
C190.0342 (16)0.0456 (17)0.0534 (18)0.0120 (14)0.0042 (14)0.0139 (14)
C200.0401 (17)0.0357 (15)0.0386 (15)0.0098 (13)0.0001 (13)0.0090 (12)
C210.056 (2)0.0414 (17)0.0386 (16)0.0147 (15)0.0066 (14)0.0127 (13)
C220.069 (2)0.0436 (19)0.059 (2)0.0122 (18)0.0079 (18)0.0116 (16)
C230.087 (3)0.0391 (19)0.077 (3)0.027 (2)0.019 (2)0.0237 (18)
C240.077 (3)0.060 (2)0.069 (2)0.040 (2)0.016 (2)0.0294 (19)
C250.053 (2)0.0531 (19)0.054 (2)0.0251 (16)0.0080 (16)0.0231 (16)
C260.0471 (18)0.0413 (16)0.0365 (15)0.0190 (14)0.0071 (13)0.0110 (13)
C270.0408 (17)0.0426 (17)0.0451 (17)0.0209 (14)0.0008 (13)0.0132 (13)
C280.0386 (16)0.0396 (16)0.0390 (15)0.0176 (13)0.0011 (12)0.0087 (12)
C290.0470 (19)0.055 (2)0.0418 (17)0.0215 (16)0.0020 (14)0.0073 (14)
C300.069 (3)0.085 (3)0.048 (2)0.042 (2)0.0133 (18)0.0127 (19)
C310.085 (3)0.110 (4)0.041 (2)0.048 (3)0.0204 (19)0.020 (2)
C320.091 (3)0.101 (3)0.046 (2)0.046 (3)0.014 (2)0.033 (2)
C330.067 (2)0.068 (2)0.0444 (18)0.033 (2)0.0078 (16)0.0209 (17)
C340.0386 (16)0.0450 (17)0.0369 (15)0.0174 (14)0.0042 (12)0.0089 (13)
C350.095 (4)0.121 (5)0.173 (7)0.059 (4)0.020 (4)0.051 (4)
C360.152 (6)0.059 (3)0.088 (4)0.021 (3)0.011 (3)0.015 (3)
Cl10.0505 (5)0.0553 (5)0.0541 (5)0.0238 (4)0.0026 (4)0.0107 (4)
Cl20.0509 (6)0.1369 (12)0.1111 (10)0.0283 (7)0.0003 (6)0.0437 (9)
N10.0427 (14)0.0419 (14)0.0340 (12)0.0185 (12)0.0018 (10)0.0073 (10)
N20.0406 (14)0.0362 (13)0.0367 (13)0.0140 (11)0.0014 (10)0.0104 (10)
N30.0361 (13)0.0414 (13)0.0370 (13)0.0161 (11)0.0012 (10)0.0066 (10)
N40.0454 (15)0.0476 (15)0.0484 (15)0.0258 (13)0.0095 (12)0.0135 (12)
N50.0383 (14)0.0405 (14)0.0377 (13)0.0118 (11)0.0009 (10)0.0097 (11)
N60.0523 (17)0.0521 (17)0.0561 (17)0.0130 (14)0.0134 (13)0.0233 (14)
N70.0419 (14)0.0426 (14)0.0370 (13)0.0196 (12)0.0048 (11)0.0127 (11)
N80.0504 (16)0.0591 (17)0.0459 (15)0.0334 (14)0.0044 (12)0.0106 (13)
N120.0435 (15)0.0448 (15)0.0465 (15)0.0085 (12)0.0026 (12)0.0116 (12)
N130.0432 (15)0.0384 (13)0.0419 (14)0.0158 (11)0.0016 (11)0.0136 (11)
O10.098 (3)0.168 (4)0.120 (3)0.091 (3)0.016 (2)0.026 (3)
O20.187 (5)0.101 (3)0.107 (3)0.023 (3)0.025 (3)0.009 (2)
O30.135 (4)0.065 (3)0.105 (4)0.028 (3)0.051 (3)0.039 (3)
C370.082 (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)
Geometric parameters (Å, º) top
Ni1—N52.076 (2)C21—N121.375 (4)
Ni1—N32.078 (2)C21—C221.394 (5)
Ni1—N132.082 (2)C21—C261.403 (5)
Ni1—N72.097 (2)C22—C231.367 (6)
Ni1—N12.167 (2)C22—H220.9300
Ni1—N22.175 (2)C23—C241.389 (6)
C1—N21.476 (4)C23—H230.9300
C1—C21.528 (4)C24—C251.382 (5)
C1—H1A0.9700C24—H240.9300
C1—H1B0.9700C25—C261.385 (4)
C2—N11.481 (4)C25—H250.9300
C2—H2A0.9700C26—N131.408 (4)
C2—H2B0.9700C27—N21.485 (4)
C3—N11.476 (4)C27—C281.494 (4)
C3—C41.498 (4)C27—H27A0.9700
C3—H3A0.9700C27—H27B0.9700
C3—H3B0.9700C28—N71.320 (4)
C4—N31.321 (4)C28—N81.340 (4)
C4—N41.339 (4)C29—C301.386 (5)
C5—C61.389 (4)C29—N81.386 (4)
C5—N31.391 (4)C29—C341.392 (4)
C5—C101.406 (4)C30—C311.354 (6)
C6—C71.377 (5)C30—H300.9300
C6—H60.9300C31—C321.397 (6)
C7—C81.397 (5)C31—H310.9300
C7—H70.9300C32—C331.378 (5)
C8—C91.372 (5)C32—H320.9300
C8—H80.9300C33—C341.393 (5)
C9—C101.387 (5)C33—H330.9300
C9—H90.9300C34—N71.394 (4)
C10—N41.371 (4)C35—O11.344 (6)
C11—C121.478 (4)C35—H35A0.9600
C11—N11.488 (4)C35—H35B0.9600
C11—H11A0.9700C35—H35C0.9600
C11—H11B0.9700C36—O21.313 (6)
C12—N51.309 (4)C36—H36A0.9600
C12—N61.345 (4)C36—H36B0.9600
C13—C141.388 (5)C36—H36C0.9600
C13—C181.400 (5)N4—H40.8600
C13—N51.407 (4)N6—H6A0.8600
C14—C151.381 (5)N8—H8A0.8600
C14—H140.9300N12—H120.8600
C15—C161.390 (6)O1—H10.8200
C15—H150.9300O2—H20.8200
C16—C171.360 (6)O3—C371.395 (7)
C16—H160.9300O3—H30.8200
C17—C181.393 (5)C37—H37A0.9600
C17—H170.9300C37—H37B0.9600
C18—N61.376 (4)C37—H37C0.9600
C19—N21.488 (4)C37'—O3'1.358 (9)
C19—C201.502 (4)C37'—H37D0.9600
C19—H19A0.9700C37'—H37E0.9600
C19—H19B0.9700C37'—H37F0.9600
C20—N131.314 (4)O3'—H3'0.8200
C20—N121.335 (4)
N5—Ni1—N391.55 (10)C22—C23—C24122.0 (3)
N5—Ni1—N13171.99 (10)C22—C23—H23119.0
N3—Ni1—N1392.50 (10)C24—C23—H23119.0
N5—Ni1—N792.35 (10)C25—C24—C23121.6 (4)
N3—Ni1—N7120.95 (10)C25—C24—H24119.2
N13—Ni1—N791.49 (10)C23—C24—H24119.2
N5—Ni1—N180.72 (9)C24—C25—C26117.5 (4)
N3—Ni1—N179.15 (9)C24—C25—H25121.2
N13—Ni1—N193.27 (9)C26—C25—H25121.2
N7—Ni1—N1159.13 (10)C25—C26—C21120.3 (3)
N5—Ni1—N293.07 (9)C25—C26—N13131.7 (3)
N3—Ni1—N2159.90 (9)C21—C26—N13108.0 (3)
N13—Ni1—N280.83 (9)N2—C27—C28105.7 (2)
N7—Ni1—N278.41 (9)N2—C27—H27A110.6
N1—Ni1—N282.31 (9)C28—C27—H27A110.6
N2—C1—C2108.7 (2)N2—C27—H27B110.6
N2—C1—H1A110.0C28—C27—H27B110.6
C2—C1—H1A110.0H27A—C27—H27B108.7
N2—C1—H1B110.0N7—C28—N8113.1 (3)
C2—C1—H1B110.0N7—C28—C27122.0 (3)
H1A—C1—H1B108.3N8—C28—C27124.9 (3)
N1—C2—C1108.6 (2)C30—C29—N8132.6 (3)
N1—C2—H2A110.0C30—C29—C34121.8 (3)
C1—C2—H2A110.0N8—C29—C34105.6 (3)
N1—C2—H2B110.0C31—C30—C29117.4 (4)
C1—C2—H2B110.0C31—C30—H30121.3
H2A—C2—H2B108.3C29—C30—H30121.3
N1—C3—C4107.2 (2)C30—C31—C32121.4 (3)
N1—C3—H3A110.3C30—C31—H31119.3
C4—C3—H3A110.3C32—C31—H31119.3
N1—C3—H3B110.3C33—C32—C31122.2 (4)
C4—C3—H3B110.3C33—C32—H32118.9
H3A—C3—H3B108.5C31—C32—H32118.9
N3—C4—N4113.0 (3)C32—C33—C34116.4 (3)
N3—C4—C3121.3 (3)C32—C33—H33121.8
N4—C4—C3125.7 (3)C34—C33—H33121.8
C6—C5—N3131.2 (3)C29—C34—C33120.8 (3)
C6—C5—C10120.4 (3)C29—C34—N7109.1 (3)
N3—C5—C10108.3 (3)C33—C34—N7130.1 (3)
C7—C6—C5117.3 (3)O1—C35—H35A109.5
C7—C6—H6121.3O1—C35—H35B109.5
C5—C6—H6121.3H35A—C35—H35B109.5
C6—C7—C8122.0 (3)O1—C35—H35C109.5
C6—C7—H7119.0H35A—C35—H35C109.5
C8—C7—H7119.0H35B—C35—H35C109.5
C9—C8—C7121.3 (3)O2—C36—H36A109.5
C9—C8—H8119.4O2—C36—H36B109.5
C7—C8—H8119.4H36A—C36—H36B109.5
C8—C9—C10117.3 (3)O2—C36—H36C109.5
C8—C9—H9121.4H36A—C36—H36C109.5
C10—C9—H9121.4H36B—C36—H36C109.5
N4—C10—C9132.5 (3)C3—N1—C2113.5 (2)
N4—C10—C5105.8 (3)C3—N1—C11111.1 (2)
C9—C10—C5121.7 (3)C2—N1—C11111.7 (2)
C12—C11—N1110.6 (2)C3—N1—Ni1104.52 (17)
C12—C11—H11A109.5C2—N1—Ni1105.47 (18)
N1—C11—H11A109.5C11—N1—Ni1110.16 (17)
C12—C11—H11B109.5C1—N2—C27114.3 (2)
N1—C11—H11B109.5C1—N2—C19111.8 (2)
H11A—C11—H11B108.1C27—N2—C19109.8 (2)
N5—C12—N6112.8 (3)C1—N2—Ni1106.06 (18)
N5—C12—C11122.9 (3)C27—N2—Ni1104.33 (17)
N6—C12—C11124.3 (3)C19—N2—Ni1110.27 (17)
C14—C13—C18120.8 (3)C4—N3—C5105.3 (2)
C14—C13—N5131.1 (3)C4—N3—Ni1110.72 (19)
C18—C13—N5108.0 (3)C5—N3—Ni1143.9 (2)
C15—C14—C13116.9 (3)C4—N4—C10107.4 (2)
C15—C14—H14121.5C4—N4—H4126.3
C13—C14—H14121.5C10—N4—H4126.3
C14—C15—C16121.8 (4)C12—N5—C13105.7 (3)
C14—C15—H15119.1C12—N5—Ni1113.6 (2)
C16—C15—H15119.1C13—N5—Ni1140.5 (2)
C17—C16—C15121.9 (4)C12—N6—C18107.6 (3)
C17—C16—H16119.1C12—N6—H6A126.2
C15—C16—H16119.1C18—N6—H6A126.2
C16—C17—C18117.2 (4)C28—N7—C34105.1 (2)
C16—C17—H17121.4C28—N7—Ni1110.24 (19)
C18—C17—H17121.4C34—N7—Ni1144.6 (2)
N6—C18—C17132.8 (4)C28—N8—C29107.1 (3)
N6—C18—C13105.8 (3)C28—N8—H8A126.4
C17—C18—C13121.3 (4)C29—N8—H8A126.4
N2—C19—C20110.3 (2)C20—N12—C21107.5 (3)
N2—C19—H19A109.6C20—N12—H12126.3
C20—C19—H19A109.6C21—N12—H12126.3
N2—C19—H19B109.6C20—N13—C26105.1 (3)
C20—C19—H19B109.6C20—N13—Ni1113.40 (19)
H19A—C19—H19B108.1C26—N13—Ni1141.5 (2)
N13—C20—N12113.5 (3)C35—O1—H1109.5
N13—C20—C19123.1 (3)C36—O2—H2109.5
N12—C20—C19123.4 (3)O3'—C37'—H37D109.5
N12—C21—C22132.3 (3)O3'—C37'—H37E109.5
N12—C21—C26105.9 (3)H37D—C37'—H37E109.5
C22—C21—C26121.8 (3)O3'—C37'—H37F109.5
C23—C22—C21116.8 (4)H37D—C37'—H37F109.5
C23—C22—H22121.6H37E—C37'—H37F109.5
C21—C22—H22121.6C37'—O3'—H3'109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···Cl1i0.822.303.117 (7)171
N4—H4···Cl1ii0.862.293.140 (3)172
N6—H6A···O3iii0.861.902.761 (5)175
N12—H12···Cl1iv0.862.293.116 (3)162
C2—H2B···O2iv0.972.253.145 (5)154
C11—H11B···Cl2iii0.972.533.445 (3)157
O1—H1···Cl20.822.273.065 (4)163
O2—H2···Cl20.822.533.027 (5)120
N8—H8A···O10.861.882.705 (4)161
C27—H27B···Cl20.972.643.582 (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
Mr806.43
Crystal system, space groupTriclinic, 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)
V3)1971.28 (16)
Z2
Radiation typeMo Kα
µ (mm1)0.68
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
17041, 7670, 6229
Rint0.031
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.145, 1.05
No. of reflections7670
No. of parameters505
No. of restraints26
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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.

Selected geometric parameters (Å, º) top
Ni1—N52.076 (2)Ni1—N72.097 (2)
Ni1—N32.078 (2)Ni1—N12.167 (2)
Ni1—N132.082 (2)Ni1—N22.175 (2)
N5—Ni1—N391.55 (10)N13—Ni1—N193.27 (9)
N5—Ni1—N13171.99 (10)N7—Ni1—N1159.13 (10)
N3—Ni1—N1392.50 (10)N5—Ni1—N293.07 (9)
N5—Ni1—N792.35 (10)N3—Ni1—N2159.90 (9)
N3—Ni1—N7120.95 (10)N13—Ni1—N280.83 (9)
N13—Ni1—N791.49 (10)N7—Ni1—N278.41 (9)
N5—Ni1—N180.72 (9)N1—Ni1—N282.31 (9)
N3—Ni1—N179.15 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···Cl1i0.822.303.117 (7)171.2
N4—H4···Cl1ii0.862.293.140 (3)172.0
N6—H6A···O3iii0.861.902.761 (5)175.1
N12—H12···Cl1iv0.862.293.116 (3)161.6
C2—H2B···O2iv0.972.253.145 (5)153.7
C11—H11B···Cl2iii0.972.533.445 (3)157.2
O1—H1···Cl20.822.273.065 (4)162.8
O2—H2···Cl20.822.533.027 (5)120.0
N8—H8A···O10.861.882.705 (4)160.8
C27—H27B···Cl20.972.643.582 (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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