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In the title complex, [Ni(EDTB)](NO3)2·CH3OH [EDTB is N,N,N′,N′-tetra­kis(benzimidazol-2-ylmeth­yl)ethane-1,2-diamine, C34H32N10], the NiII ion is coordinated by six N atoms of the EDTB ligand to form a distorted octa­hedral geometry. The crystal packing is stabilized by inter­molecular N—H...O, N—H...N and O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039681/rz6141sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039681/rz6141Isup2.hkl
Contains datablock I

CCDC reference: 226003

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.044
  • wR factor = 0.119
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N11 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N12 PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 55.00 A   3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Some benzimidazole derivatives can be used as building blocks in the synthesis of model complexes (Ogawa et al., 1998; Liu et al., 2002; Blackburn et al., 1989; Plengea et al., 2003). The hexadentate polyfunctional benzimidazole ligand EDTB [EDTB is N,N,N',N'-tetrakis(2-benzimidazolylmethyl)-1,2-ethanediamine] has attracted considerable attention in recent years, and a series of compounds containing this ligand have been reported. Among these, [Mn(EDTB)(Ac)](Ac)·C2H5OH (Liao et al., 2001) shows SOD-like activity, while Cu(EDTB)(NO3)2·C2H5OH (Chen et al., 2004) exhibits catecholase-like activity. As an extension of this work, we have synthesized the title compound, (I), and report its crystal structure here.

The asymmetric unit of (I) consists of an [Ni(EDTB)]2+ cation, two NO3 anions and a methanol molecule (Fig. 1). Selected bond lengths and angles are listed in Table 1. The NiII ion is six-coordinated by four benzimidazole and two amino N atoms, forming a distorted octahedral geometry. The equatorial plane is made up by the N atoms of two benzimidazole groups [Ni—N1 = 2.046 (2) Å and Ni—N7 = 2.095 (2) Å] and two amino N atoms [Ni—N3 = 2.186 (2) Å and Ni—N6 = 2.137 (2) Å], while the axial positions are occupied the N atoms of the other two benzimidazole groups [Ni—N4 = 2.094 (2) Å and Ni—N9 = 2.098 (2) Å]. The N4—Ni1—N9 angle is 171.40 (8)°, and the Ni atom is displaced by 0.023 (5) Å from the equatorial plane. The crystal packing is stabilized by intermolecular N—H···O, N—H···N and O—H···O hydrogen bonds (Table 2).

Experimental top

EDTB was prepared as described previously by Gomez-Romero et al. (1990). EDTB (1 mmol) was dissolved in hot methanol (15 ml) and a solution of Ni(NO3)2·6H2O (1 mmol) in water (10 ml) was added dropwise. The mixture was filtered after continuous stirring for 3 h. Violet single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of the solution at room temperature over a week. Analysis calculated for C35H36N12NiO7: C 56.55, H 4.34, N 22.61%; found: C 57.46,H 4.52,N 23.02%.

Refinement top

All H atoms were placed in calculated positions, with C—H = 0.86 [0.93 in CIF?]–0.97 Å, O—H = 0.82 Å and N—H = 0.86 Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2 or 1.5 times Ueq(parent atom).

Computing details top

Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-NT (Bruker, 1998); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Bruker, 1998); software used to prepare material for publication: SHELXTL-NT.

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, with 30% probability displacement ellipsoids. H atoms have been omitted for clarity.
[N,N,N',N'-Tetrakis(benzimidazol-2-ylmethyl)ethane-1,2-diamine]nickel(II) dinitrate methanol solvate top
Crystal data top
[nI(C34H32N10)](NO3)2·CH4OZ = 2
Mr = 795.47F(000) = 828
Triclinic, P1Dx = 1.452 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.718 (4) ÅCell parameters from 875 reflections
b = 12.103 (4) Åθ = 3.3–25.0°
c = 14.528 (5) ŵ = 0.60 mm1
α = 91.409 (5)°T = 293 K
β = 103.988 (5)°Prism, violet
γ = 113.291 (5)°0.22 × 0.18 × 0.14 mm
V = 1819.6 (10) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
7392 independent reflections
Radiation source: fine-focus sealed tube5192 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ϕ and ω scansθmax = 26.4°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.878, Tmax = 0.919k = 1514
10574 measured reflectionsl = 1817
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0602P)2]
where P = (Fo2 + 2Fc2)/3
7392 reflections(Δ/σ)max = 0.001
498 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.38 e Å3
Crystal data top
[nI(C34H32N10)](NO3)2·CH4Oγ = 113.291 (5)°
Mr = 795.47V = 1819.6 (10) Å3
Triclinic, P1Z = 2
a = 11.718 (4) ÅMo Kα radiation
b = 12.103 (4) ŵ = 0.60 mm1
c = 14.528 (5) ÅT = 293 K
α = 91.409 (5)°0.22 × 0.18 × 0.14 mm
β = 103.988 (5)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
7392 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5192 reflections with I > 2σ(I)
Tmin = 0.878, Tmax = 0.919Rint = 0.026
10574 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.119H-atom parameters constrained
S = 1.02Δρmax = 0.43 e Å3
7392 reflectionsΔρmin = 0.38 e Å3
498 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*/Ueq
Ni10.61558 (3)0.80491 (3)0.71156 (2)0.03094 (12)
N10.4779 (2)0.8354 (2)0.75831 (15)0.0327 (5)
N20.3189 (2)0.8955 (2)0.72042 (16)0.0418 (6)
H20.26310.91820.68630.050*
N30.4702 (2)0.7759 (2)0.57592 (15)0.0362 (5)
N40.5047 (2)0.6186 (2)0.70359 (16)0.0372 (5)
N50.3081 (2)0.4705 (2)0.64662 (17)0.0430 (6)
H5A0.23230.42960.60880.052*
N60.7271 (2)0.7847 (2)0.62101 (15)0.0376 (5)
N70.7741 (2)0.7993 (2)0.81237 (15)0.0355 (5)
N80.9139 (2)0.7142 (2)0.83320 (18)0.0472 (6)
H80.95710.67590.81950.057*
N90.7136 (2)0.9882 (2)0.69742 (15)0.0334 (5)
N100.8568 (2)1.1200 (2)0.63321 (16)0.0412 (6)
H100.91571.14780.60380.049*
C10.4165 (3)0.8654 (3)0.58962 (18)0.0393 (7)
H1A0.33300.84270.54370.047*
H1B0.47400.94550.58080.047*
C20.4031 (3)0.8658 (2)0.68985 (19)0.0347 (6)
C30.3372 (3)0.8834 (3)0.8164 (2)0.0379 (7)
C40.2765 (3)0.8989 (3)0.8836 (2)0.0491 (8)
H40.21030.92500.86810.059*
C50.3189 (3)0.8740 (3)0.9740 (2)0.0524 (8)
H50.28130.88481.02110.063*
C60.4172 (3)0.8327 (3)0.9974 (2)0.0482 (8)
H60.44250.81611.05930.058*
C70.4769 (3)0.8162 (3)0.93121 (19)0.0397 (7)
H70.54110.78760.94670.048*
C80.4374 (3)0.8442 (2)0.83978 (19)0.0338 (6)
C90.3667 (3)0.6498 (3)0.5575 (2)0.0436 (7)
H9A0.28420.65300.55330.052*
H9B0.36110.60990.49680.052*
C100.3942 (3)0.5787 (3)0.63524 (19)0.0365 (6)
C110.3633 (3)0.4366 (3)0.7298 (2)0.0412 (7)
C120.3163 (3)0.3379 (3)0.7778 (2)0.0575 (9)
H120.23390.27630.75380.069*
C130.3980 (4)0.3358 (3)0.8630 (3)0.0603 (9)
H130.36990.27090.89720.072*
C140.5215 (3)0.4278 (3)0.8996 (2)0.0527 (8)
H140.57340.42280.95740.063*
C150.5683 (3)0.5257 (3)0.8525 (2)0.0445 (7)
H150.65080.58690.87740.053*
C160.4877 (3)0.5300 (2)0.7657 (2)0.0365 (6)
C170.5443 (3)0.7981 (3)0.50338 (19)0.0419 (7)
H17A0.59290.88460.50550.050*
H17B0.48530.76640.43990.050*
C180.6363 (3)0.7356 (3)0.52432 (19)0.0451 (7)
H18A0.58730.64890.52080.054*
H18B0.68430.74900.47680.054*
C190.7813 (3)0.7001 (3)0.6653 (2)0.0459 (8)
H19A0.71620.61720.64970.055*
H19B0.85390.70490.64210.055*
C200.8240 (3)0.7378 (3)0.7707 (2)0.0385 (7)
C210.9243 (3)0.7629 (3)0.9237 (2)0.0431 (7)
C220.9982 (3)0.7635 (3)1.0147 (2)0.0587 (9)
H221.05440.72541.02390.070*
C230.9846 (3)0.8228 (4)1.0900 (2)0.0646 (10)
H231.03250.82461.15170.078*
C240.9013 (3)0.8806 (3)1.0769 (2)0.0551 (9)
H240.89550.92081.12980.066*
C250.8272 (3)0.8796 (3)0.9873 (2)0.0418 (7)
H250.77200.91870.97880.050*
C260.8376 (3)0.8181 (2)0.90997 (19)0.0351 (6)
C270.8343 (3)0.9041 (3)0.6229 (2)0.0407 (7)
H27A0.91270.90990.66860.049*
H27B0.84980.91080.56030.049*
C280.8016 (3)1.0048 (3)0.65025 (18)0.0353 (6)
C290.8020 (3)1.1857 (3)0.67138 (19)0.0386 (7)
C300.8225 (3)1.3071 (3)0.6754 (2)0.0510 (8)
H300.88151.36190.64770.061*
C310.7511 (4)1.3422 (3)0.7225 (2)0.0554 (9)
H310.76291.42300.72730.066*
C320.6613 (3)1.2602 (3)0.7632 (2)0.0507 (8)
H320.61441.28770.79370.061*
C330.6401 (3)1.1398 (3)0.75960 (19)0.0407 (7)
H330.58041.08580.78720.049*
C340.7122 (3)1.1020 (2)0.71255 (17)0.0332 (6)
N110.0089 (3)0.3620 (3)0.4772 (2)0.0530 (7)
O10.0971 (3)0.4380 (2)0.45105 (18)0.0726 (7)
O20.0999 (3)0.3160 (3)0.4240 (2)0.1089 (11)
O30.0358 (3)0.3350 (3)0.5592 (2)0.0800 (8)
N120.1501 (3)0.0537 (3)0.62839 (18)0.0534 (7)
O40.1007 (3)0.1209 (2)0.59058 (17)0.0694 (7)
O50.1351 (2)0.0184 (3)0.70521 (17)0.0770 (8)
O60.2163 (3)0.0215 (3)0.58863 (18)0.0862 (9)
O70.0475 (3)0.6036 (3)0.76333 (19)0.0738 (7)
H7A0.05000.61140.70790.111*
C350.1346 (4)0.5554 (4)0.8067 (4)0.1025 (16)
H35A0.21990.60770.80380.154*
H35B0.10970.47630.77360.154*
H35C0.13410.54920.87230.154*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.03129 (19)0.0356 (2)0.02798 (19)0.01471 (15)0.00984 (15)0.00751 (14)
N10.0316 (12)0.0382 (13)0.0316 (12)0.0156 (10)0.0116 (10)0.0112 (10)
N20.0342 (13)0.0525 (16)0.0422 (14)0.0236 (12)0.0066 (11)0.0100 (12)
N30.0373 (13)0.0414 (14)0.0294 (12)0.0157 (11)0.0089 (10)0.0072 (10)
N40.0383 (13)0.0350 (13)0.0377 (13)0.0153 (11)0.0090 (11)0.0090 (11)
N50.0380 (13)0.0375 (14)0.0424 (14)0.0069 (11)0.0069 (12)0.0035 (11)
N60.0440 (14)0.0417 (14)0.0312 (12)0.0204 (12)0.0132 (11)0.0033 (11)
N70.0356 (13)0.0406 (14)0.0333 (12)0.0182 (11)0.0099 (11)0.0077 (10)
N80.0442 (15)0.0562 (17)0.0539 (16)0.0332 (13)0.0135 (13)0.0122 (13)
N90.0336 (12)0.0397 (13)0.0294 (12)0.0150 (10)0.0131 (10)0.0073 (10)
N100.0356 (13)0.0461 (15)0.0383 (13)0.0077 (11)0.0192 (11)0.0091 (11)
C10.0405 (16)0.0467 (17)0.0325 (15)0.0205 (14)0.0080 (13)0.0137 (13)
C20.0292 (14)0.0386 (16)0.0364 (15)0.0149 (12)0.0078 (12)0.0067 (13)
C30.0308 (15)0.0412 (17)0.0406 (16)0.0130 (13)0.0111 (13)0.0032 (13)
C40.0391 (17)0.055 (2)0.059 (2)0.0224 (15)0.0183 (16)0.0027 (16)
C50.053 (2)0.061 (2)0.0500 (19)0.0224 (17)0.0284 (17)0.0045 (17)
C60.057 (2)0.051 (2)0.0389 (17)0.0185 (16)0.0232 (16)0.0119 (15)
C70.0412 (16)0.0456 (17)0.0362 (15)0.0190 (14)0.0151 (13)0.0124 (13)
C80.0296 (14)0.0346 (15)0.0379 (15)0.0105 (12)0.0149 (12)0.0076 (12)
C90.0427 (17)0.0444 (18)0.0347 (16)0.0122 (14)0.0047 (14)0.0045 (14)
C100.0355 (15)0.0366 (16)0.0340 (15)0.0117 (13)0.0094 (13)0.0031 (13)
C110.0463 (17)0.0368 (16)0.0425 (17)0.0176 (14)0.0146 (15)0.0064 (13)
C120.054 (2)0.0401 (19)0.071 (2)0.0093 (16)0.0204 (19)0.0157 (17)
C130.065 (2)0.049 (2)0.069 (2)0.0208 (18)0.026 (2)0.0308 (18)
C140.062 (2)0.051 (2)0.0482 (19)0.0259 (18)0.0153 (17)0.0174 (16)
C150.0456 (17)0.0370 (17)0.0468 (18)0.0149 (14)0.0090 (15)0.0101 (14)
C160.0400 (16)0.0310 (15)0.0401 (16)0.0152 (13)0.0129 (13)0.0066 (13)
C170.0454 (17)0.0522 (19)0.0249 (14)0.0164 (15)0.0107 (13)0.0069 (13)
C180.0545 (19)0.0516 (19)0.0303 (15)0.0204 (16)0.0165 (14)0.0015 (14)
C190.0531 (19)0.0508 (19)0.0428 (17)0.0311 (16)0.0127 (15)0.0026 (15)
C200.0346 (15)0.0419 (17)0.0452 (17)0.0213 (13)0.0118 (14)0.0089 (14)
C210.0335 (16)0.0493 (18)0.0461 (18)0.0170 (14)0.0096 (14)0.0119 (15)
C220.0384 (18)0.076 (3)0.060 (2)0.0281 (18)0.0032 (17)0.0217 (19)
C230.049 (2)0.089 (3)0.0413 (19)0.021 (2)0.0005 (17)0.0139 (19)
C240.0463 (19)0.070 (2)0.0378 (17)0.0130 (17)0.0103 (15)0.0065 (16)
C250.0364 (16)0.0461 (18)0.0384 (16)0.0122 (14)0.0104 (14)0.0067 (14)
C260.0281 (14)0.0357 (15)0.0365 (15)0.0087 (12)0.0075 (12)0.0076 (12)
C270.0376 (16)0.0521 (19)0.0355 (15)0.0174 (14)0.0174 (13)0.0067 (14)
C280.0319 (14)0.0435 (17)0.0273 (14)0.0111 (13)0.0100 (12)0.0050 (12)
C290.0382 (16)0.0413 (17)0.0308 (15)0.0095 (13)0.0117 (13)0.0069 (13)
C300.058 (2)0.0403 (18)0.0450 (18)0.0084 (15)0.0179 (16)0.0116 (15)
C310.073 (2)0.0342 (18)0.053 (2)0.0170 (17)0.0149 (18)0.0042 (15)
C320.066 (2)0.0470 (19)0.0456 (18)0.0268 (17)0.0201 (17)0.0036 (15)
C330.0472 (17)0.0412 (17)0.0361 (16)0.0169 (14)0.0176 (14)0.0089 (13)
C340.0360 (15)0.0360 (15)0.0246 (13)0.0123 (12)0.0076 (12)0.0043 (12)
N110.0452 (17)0.0504 (18)0.0631 (19)0.0207 (14)0.0137 (16)0.0047 (15)
O10.0745 (18)0.0668 (17)0.0691 (17)0.0156 (14)0.0302 (15)0.0084 (13)
O20.0481 (17)0.122 (3)0.121 (3)0.0246 (17)0.0162 (18)0.034 (2)
O30.0740 (18)0.083 (2)0.0782 (19)0.0231 (15)0.0262 (16)0.0337 (16)
N120.0487 (16)0.074 (2)0.0416 (16)0.0288 (15)0.0139 (13)0.0096 (14)
O40.0754 (17)0.0917 (19)0.0723 (16)0.0584 (16)0.0324 (14)0.0275 (15)
O50.0619 (16)0.128 (2)0.0495 (14)0.0403 (16)0.0258 (13)0.0337 (15)
O60.118 (2)0.143 (3)0.0644 (16)0.105 (2)0.0506 (17)0.0467 (17)
O70.0801 (18)0.0835 (19)0.0766 (17)0.0501 (16)0.0268 (16)0.0068 (16)
C350.076 (3)0.090 (3)0.141 (4)0.050 (3)0.002 (3)0.006 (3)
Geometric parameters (Å, º) top
Ni1—N12.046 (2)C12—C131.377 (4)
Ni1—N42.094 (2)C12—H120.9300
Ni1—N72.095 (2)C13—C141.393 (5)
Ni1—N92.098 (2)C13—H130.9300
Ni1—N62.137 (2)C14—C151.371 (4)
Ni1—N32.186 (2)C14—H140.9300
N1—C21.321 (3)C15—C161.397 (4)
N1—C81.394 (3)C15—H150.9300
N2—C21.336 (3)C17—C181.524 (4)
N2—C31.380 (3)C17—H17A0.9700
N2—H20.8600C17—H17B0.9700
N3—C11.482 (3)C18—H18A0.9700
N3—C171.486 (3)C18—H18B0.9700
N3—C91.494 (4)C19—C201.488 (4)
N4—C101.325 (3)C19—H19A0.9700
N4—C161.404 (3)C19—H19B0.9700
N5—C101.345 (4)C21—C221.393 (4)
N5—C111.380 (4)C21—C261.402 (4)
N5—H5A0.8600C22—C231.368 (5)
N6—C181.482 (3)C22—H220.9300
N6—C271.487 (4)C23—C241.391 (5)
N6—C191.489 (3)C23—H230.9300
N7—C201.325 (3)C24—C251.376 (4)
N7—C261.399 (3)C24—H240.9300
N8—C201.343 (3)C25—C261.388 (4)
N8—C211.384 (4)C25—H250.9300
N8—H80.8600C27—C281.485 (4)
N9—C281.326 (3)C27—H27A0.9700
N9—C341.397 (3)C27—H27B0.9700
N10—C281.343 (3)C29—C301.389 (4)
N10—C291.381 (4)C29—C341.408 (4)
N10—H100.8600C30—C311.376 (5)
C1—C21.502 (4)C30—H300.9300
C1—H1A0.9700C31—C321.395 (5)
C1—H1B0.9700C31—H310.9300
C3—C41.388 (4)C32—C331.375 (4)
C3—C81.406 (4)C32—H320.9300
C4—C51.373 (4)C33—C341.400 (4)
C4—H40.9300C33—H330.9300
C5—C61.402 (4)N11—O21.214 (3)
C5—H50.9300N11—O11.230 (4)
C6—C71.371 (4)N11—O31.243 (3)
C6—H60.9300N12—O51.232 (3)
C7—C81.393 (4)N12—O61.239 (3)
C7—H70.9300N12—O41.240 (3)
C9—C101.487 (4)O7—C351.399 (4)
C9—H9A0.9700O7—H7A0.8200
C9—H9B0.9700C35—H35A0.9600
C11—C121.386 (4)C35—H35B0.9600
C11—C161.406 (4)C35—H35C0.9600
N1—Ni1—N488.09 (9)C11—C12—H12121.7
N1—Ni1—N7119.12 (9)C12—C13—C14122.0 (3)
N4—Ni1—N792.81 (9)C12—C13—H13119.0
N1—Ni1—N993.07 (9)C14—C13—H13119.0
N4—Ni1—N9171.40 (8)C15—C14—C13121.7 (3)
N7—Ni1—N994.07 (9)C15—C14—H14119.2
N1—Ni1—N6161.62 (8)C13—C14—H14119.2
N4—Ni1—N695.20 (9)C14—C15—C16117.5 (3)
N7—Ni1—N678.85 (9)C14—C15—H15121.2
N9—Ni1—N681.09 (9)C16—C15—H15121.2
N1—Ni1—N379.18 (9)C15—C16—N4131.2 (3)
N4—Ni1—N380.49 (9)C15—C16—C11120.2 (3)
N7—Ni1—N3160.51 (9)N4—C16—C11108.6 (2)
N9—Ni1—N391.35 (8)N3—C17—C18109.3 (2)
N6—Ni1—N383.54 (9)N3—C17—H17A109.8
C2—N1—C8105.4 (2)C18—C17—H17A109.8
C2—N1—Ni1111.63 (17)N3—C17—H17B109.8
C8—N1—Ni1142.81 (17)C18—C17—H17B109.8
C2—N2—C3107.9 (2)H17A—C17—H17B108.3
C2—N2—H2126.1N6—C18—C17109.9 (2)
C3—N2—H2126.1N6—C18—H18A109.7
C1—N3—C17115.4 (2)C17—C18—H18A109.7
C1—N3—C9110.4 (2)N6—C18—H18B109.7
C17—N3—C9111.6 (2)C17—C18—H18B109.7
C1—N3—Ni1103.90 (15)H18A—C18—H18B108.2
C17—N3—Ni1104.04 (16)C20—C19—N6106.8 (2)
C9—N3—Ni1110.96 (16)C20—C19—H19A110.4
C10—N4—C16105.3 (2)N6—C19—H19A110.4
C10—N4—Ni1112.85 (17)C20—C19—H19B110.4
C16—N4—Ni1137.56 (19)N6—C19—H19B110.4
C10—N5—C11107.8 (2)H19A—C19—H19B108.6
C10—N5—H5A126.1N7—C20—N8112.9 (3)
C11—N5—H5A126.1N7—C20—C19121.9 (2)
C18—N6—C27112.6 (2)N8—C20—C19125.2 (3)
C18—N6—C19114.0 (2)N8—C21—C22133.0 (3)
C27—N6—C19109.5 (2)N8—C21—C26105.6 (2)
C18—N6—Ni1106.23 (17)C22—C21—C26121.5 (3)
C27—N6—Ni1109.56 (16)C23—C22—C21117.1 (3)
C19—N6—Ni1104.44 (16)C23—C22—H22121.5
C20—N7—C26105.3 (2)C21—C22—H22121.5
C20—N7—Ni1108.97 (17)C22—C23—C24121.9 (3)
C26—N7—Ni1144.66 (18)C22—C23—H23119.1
C20—N8—C21107.5 (2)C24—C23—H23119.1
C20—N8—H8126.3C25—C24—C23121.4 (3)
C21—N8—H8126.3C25—C24—H24119.3
C28—N9—C34105.2 (2)C23—C24—H24119.3
C28—N9—Ni1112.28 (18)C24—C25—C26117.7 (3)
C34—N9—Ni1142.14 (18)C24—C25—H25121.1
C28—N10—C29107.9 (2)C26—C25—H25121.1
C28—N10—H10126.1C25—C26—N7130.9 (3)
C29—N10—H10126.1C25—C26—C21120.4 (3)
N3—C1—C2107.0 (2)N7—C26—C21108.7 (2)
N3—C1—H1A110.3C28—C27—N6110.4 (2)
C2—C1—H1A110.3C28—C27—H27A109.6
N3—C1—H1B110.3N6—C27—H27A109.6
C2—C1—H1B110.3C28—C27—H27B109.6
H1A—C1—H1B108.6N6—C27—H27B109.6
N1—C2—N2112.9 (2)H27A—C27—H27B108.1
N1—C2—C1121.2 (2)N9—C28—N10112.8 (2)
N2—C2—C1126.0 (2)N9—C28—C27121.6 (2)
N2—C3—C4133.2 (3)N10—C28—C27125.6 (2)
N2—C3—C8105.2 (2)N10—C29—C30132.7 (3)
C4—C3—C8121.6 (3)N10—C29—C34105.2 (2)
C5—C4—C3116.8 (3)C30—C29—C34122.1 (3)
C5—C4—H4121.6C31—C30—C29116.6 (3)
C3—C4—H4121.6C31—C30—H30121.7
C4—C5—C6121.8 (3)C29—C30—H30121.7
C4—C5—H5119.1C30—C31—C32121.9 (3)
C6—C5—H5119.1C30—C31—H31119.0
C7—C6—C5121.7 (3)C32—C31—H31119.0
C7—C6—H6119.1C33—C32—C31122.0 (3)
C5—C6—H6119.1C33—C32—H32119.0
C6—C7—C8117.2 (3)C31—C32—H32119.0
C6—C7—H7121.4C32—C33—C34117.2 (3)
C8—C7—H7121.4C32—C33—H33121.4
C7—C8—N1130.5 (2)C34—C33—H33121.4
C7—C8—C3120.8 (3)N9—C34—C33130.9 (3)
N1—C8—C3108.7 (2)N9—C34—C29108.9 (2)
C10—C9—N3110.8 (2)C33—C34—C29120.2 (3)
C10—C9—H9A109.5O2—N11—O1120.4 (4)
N3—C9—H9A109.5O2—N11—O3122.0 (4)
C10—C9—H9B109.5O1—N11—O3117.6 (3)
N3—C9—H9B109.5O5—N12—O6118.9 (3)
H9A—C9—H9B108.1O5—N12—O4121.4 (3)
N4—C10—N5112.8 (2)O6—N12—O4119.7 (3)
N4—C10—C9123.3 (3)C35—O7—H7A109.5
N5—C10—C9123.9 (3)O7—C35—H35A109.5
N5—C11—C12132.3 (3)O7—C35—H35B109.5
N5—C11—C16105.6 (3)H35A—C35—H35B109.5
C12—C11—C16122.1 (3)O7—C35—H35C109.5
C13—C12—C11116.5 (3)H35A—C35—H35C109.5
C13—C12—H12121.7H35B—C35—H35C109.5
N4—Ni1—N1—C2103.3 (2)C4—C3—C8—N1179.2 (3)
N7—Ni1—N1—C2164.51 (18)C1—N3—C9—C10116.4 (2)
N9—Ni1—N1—C268.1 (2)C17—N3—C9—C10113.8 (3)
N6—Ni1—N1—C22.6 (4)Ni1—N3—C9—C101.7 (3)
N3—Ni1—N1—C222.67 (19)C16—N4—C10—N51.4 (3)
N4—Ni1—N1—C882.9 (3)Ni1—N4—C10—N5162.37 (19)
N7—Ni1—N1—C89.3 (3)C16—N4—C10—C9175.5 (3)
N9—Ni1—N1—C8105.7 (3)Ni1—N4—C10—C914.5 (3)
N6—Ni1—N1—C8176.4 (3)C11—N5—C10—N41.7 (3)
N3—Ni1—N1—C8163.5 (3)C11—N5—C10—C9175.2 (3)
N1—Ni1—N3—C135.43 (17)N3—C9—C10—N48.5 (4)
N4—Ni1—N3—C1125.29 (18)N3—C9—C10—N5168.0 (3)
N7—Ni1—N3—C1163.6 (2)C10—N5—C11—C12176.4 (3)
N9—Ni1—N3—C157.43 (17)C10—N5—C11—C161.2 (3)
N6—Ni1—N3—C1138.30 (18)N5—C11—C12—C13177.2 (3)
N1—Ni1—N3—C17156.64 (18)C16—C11—C12—C130.0 (5)
N4—Ni1—N3—C17113.50 (18)C11—C12—C13—C140.1 (5)
N7—Ni1—N3—C1742.4 (3)C12—C13—C14—C150.0 (6)
N9—Ni1—N3—C1763.77 (17)C13—C14—C15—C160.2 (5)
N6—Ni1—N3—C1717.10 (17)C14—C15—C16—N4176.9 (3)
N1—Ni1—N3—C983.22 (19)C14—C15—C16—C110.3 (4)
N4—Ni1—N3—C96.64 (18)C10—N4—C16—C15176.2 (3)
N7—Ni1—N3—C977.7 (3)Ni1—N4—C16—C1522.7 (5)
N9—Ni1—N3—C9176.08 (18)C10—N4—C16—C110.6 (3)
N6—Ni1—N3—C9103.04 (19)Ni1—N4—C16—C11154.2 (2)
N1—Ni1—N4—C1068.3 (2)N5—C11—C16—C15177.6 (2)
N7—Ni1—N4—C10172.63 (19)C12—C11—C16—C150.2 (5)
N6—Ni1—N4—C1093.6 (2)N5—C11—C16—N40.3 (3)
N3—Ni1—N4—C1011.05 (19)C12—C11—C16—N4177.5 (3)
N1—Ni1—N4—C1683.9 (3)C1—N3—C17—C18157.2 (2)
N7—Ni1—N4—C1635.2 (3)C9—N3—C17—C1875.6 (3)
N6—Ni1—N4—C16114.2 (3)Ni1—N3—C17—C1844.1 (3)
N3—Ni1—N4—C16163.2 (3)C27—N6—C18—C1779.0 (3)
N1—Ni1—N6—C1832.7 (4)C19—N6—C18—C17155.4 (2)
N4—Ni1—N6—C1866.99 (18)Ni1—N6—C18—C1741.0 (3)
N7—Ni1—N6—C18158.83 (18)N3—C17—C18—N660.0 (3)
N9—Ni1—N6—C18105.20 (18)C18—N6—C19—C20157.6 (2)
N3—Ni1—N6—C1812.80 (17)C27—N6—C19—C2075.2 (3)
N1—Ni1—N6—C2789.3 (3)Ni1—N6—C19—C2042.1 (3)
N4—Ni1—N6—C27171.09 (17)C26—N7—C20—N80.6 (3)
N7—Ni1—N6—C2779.25 (18)Ni1—N7—C20—N8170.71 (19)
N9—Ni1—N6—C2716.73 (17)C26—N7—C20—C19179.8 (3)
N3—Ni1—N6—C27109.12 (18)Ni1—N7—C20—C198.9 (3)
N1—Ni1—N6—C19153.5 (3)C21—N8—C20—N70.4 (4)
N4—Ni1—N6—C1953.87 (19)C21—N8—C20—C19179.2 (3)
N7—Ni1—N6—C1937.98 (18)N6—C19—C20—N723.8 (4)
N9—Ni1—N6—C19133.95 (19)N6—C19—C20—N8156.6 (3)
N3—Ni1—N6—C19133.65 (19)C20—N8—C21—C22178.1 (3)
N1—Ni1—N7—C20157.87 (18)C20—N8—C21—C261.2 (3)
N4—Ni1—N7—C2068.5 (2)N8—C21—C22—C23179.3 (3)
N9—Ni1—N7—C20106.3 (2)C26—C21—C22—C231.4 (5)
N6—Ni1—N7—C2026.26 (19)C21—C22—C23—C240.2 (6)
N3—Ni1—N7—C200.6 (4)C22—C23—C24—C250.8 (6)
N1—Ni1—N7—C267.5 (4)C23—C24—C25—C260.4 (5)
N4—Ni1—N7—C2696.9 (3)C24—C25—C26—N7178.6 (3)
N9—Ni1—N7—C2688.3 (3)C24—C25—C26—C212.0 (4)
N6—Ni1—N7—C26168.4 (3)C20—N7—C26—C25178.1 (3)
N3—Ni1—N7—C26165.9 (3)Ni1—N7—C26—C2516.2 (5)
N1—Ni1—N9—C28168.38 (18)C20—N7—C26—C211.3 (3)
N7—Ni1—N9—C2872.12 (18)Ni1—N7—C26—C21164.3 (2)
N6—Ni1—N9—C285.90 (17)N8—C21—C26—C25178.0 (3)
N3—Ni1—N9—C2889.15 (18)C22—C21—C26—C252.6 (5)
N1—Ni1—N9—C343.2 (3)N8—C21—C26—N71.6 (3)
N7—Ni1—N9—C34116.3 (3)C22—C21—C26—N7177.8 (3)
N6—Ni1—N9—C34165.7 (3)C18—N6—C27—C2894.1 (3)
N3—Ni1—N9—C3482.5 (3)C19—N6—C27—C28137.9 (2)
C17—N3—C1—C2153.8 (2)Ni1—N6—C27—C2823.9 (3)
C9—N3—C1—C278.5 (3)C34—N9—C28—N100.3 (3)
Ni1—N3—C1—C240.5 (2)Ni1—N9—C28—N10174.35 (17)
C8—N1—C2—N21.1 (3)C34—N9—C28—C27178.3 (2)
Ni1—N1—C2—N2175.06 (18)Ni1—N9—C28—C277.0 (3)
C8—N1—C2—C1179.1 (2)C29—N10—C28—N90.1 (3)
Ni1—N1—C2—C14.8 (3)C29—N10—C28—C27178.7 (2)
C3—N2—C2—N10.6 (3)N6—C27—C28—N921.6 (3)
C3—N2—C2—C1179.6 (3)N6—C27—C28—N10160.0 (2)
N3—C1—C2—N126.7 (4)C28—N10—C29—C30179.3 (3)
N3—C1—C2—N2153.5 (3)C28—N10—C29—C340.5 (3)
C2—N2—C3—C4178.3 (3)N10—C29—C30—C31178.2 (3)
C2—N2—C3—C80.2 (3)C34—C29—C30—C310.4 (4)
N2—C3—C4—C5177.8 (3)C29—C30—C31—C320.7 (5)
C8—C3—C4—C50.1 (5)C30—C31—C32—C330.7 (5)
C3—C4—C5—C61.1 (5)C31—C32—C33—C340.3 (4)
C4—C5—C6—C70.6 (5)C28—N9—C34—C33178.9 (3)
C5—C6—C7—C81.1 (5)Ni1—N9—C34—C339.1 (5)
C6—C7—C8—N1179.0 (3)C28—N9—C34—C290.7 (3)
C6—C7—C8—C32.2 (4)Ni1—N9—C34—C29171.3 (2)
C2—N1—C8—C7175.9 (3)C32—C33—C34—N9179.6 (3)
Ni1—N1—C8—C710.1 (5)C32—C33—C34—C290.0 (4)
C2—N1—C8—C31.1 (3)N10—C29—C34—N90.7 (3)
Ni1—N1—C8—C3172.9 (2)C30—C29—C34—N9179.7 (3)
N2—C3—C8—C7176.6 (3)N10—C29—C34—C33178.9 (2)
C4—C3—C8—C71.8 (4)C30—C29—C34—C330.1 (4)
N2—C3—C8—N10.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O6i0.862.032.813 (3)151
N2—H2···O5i0.862.333.035 (3)140
N2—H2···N12i0.862.533.348 (4)159
N5—H5A···O30.862.052.879 (4)161
N5—H5A···O10.862.483.182 (4)139
N8—H8···O7ii0.861.922.763 (3)168
N10—H10···O3iii0.862.353.040 (4)137
N10—H10···O4iii0.862.373.063 (3)139
O7—H7A···O2iv0.822.243.032 (5)164
O7—H7A···O1iv0.822.423.086 (4)139
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x+1, y+1, z; (iv) x, y+1, z+1.

Experimental details

Crystal data
Chemical formula[nI(C34H32N10)](NO3)2·CH4O
Mr795.47
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)11.718 (4), 12.103 (4), 14.528 (5)
α, β, γ (°)91.409 (5), 103.988 (5), 113.291 (5)
V3)1819.6 (10)
Z2
Radiation typeMo Kα
µ (mm1)0.60
Crystal size (mm)0.22 × 0.18 × 0.14
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.878, 0.919
No. of measured, independent and
observed [I > 2σ(I)] reflections
10574, 7392, 5192
Rint0.026
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.119, 1.02
No. of reflections7392
No. of parameters498
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.43, 0.38

Computer programs: SMART-NT (Bruker, 1998), SAINT-NT (Bruker, 1998), SAINT-NT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-NT (Bruker, 1998), SHELXTL-NT.

Selected geometric parameters (Å, º) top
Ni1—N12.046 (2)Ni1—N92.098 (2)
Ni1—N42.094 (2)Ni1—N62.137 (2)
Ni1—N72.095 (2)Ni1—N32.186 (2)
N1—Ni1—N488.09 (9)N7—Ni1—N678.85 (9)
N1—Ni1—N7119.12 (9)N9—Ni1—N681.09 (9)
N4—Ni1—N792.81 (9)N1—Ni1—N379.18 (9)
N1—Ni1—N993.07 (9)N4—Ni1—N380.49 (9)
N4—Ni1—N9171.40 (8)N7—Ni1—N3160.51 (9)
N7—Ni1—N994.07 (9)N9—Ni1—N391.35 (8)
N1—Ni1—N6161.62 (8)N6—Ni1—N383.54 (9)
N4—Ni1—N695.20 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O6i0.862.032.813 (3)151
N2—H2···O5i0.862.333.035 (3)140
N2—H2···N12i0.862.533.348 (4)159
N5—H5A···O30.862.052.879 (4)161
N5—H5A···O10.862.483.182 (4)139
N8—H8···O7ii0.861.922.763 (3)168
N10—H10···O3iii0.862.353.040 (4)137
N10—H10···O4iii0.862.373.063 (3)139
O7—H7A···O2iv0.822.243.032 (5)164
O7—H7A···O1iv0.822.423.086 (4)139
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x+1, y+1, z; (iv) x, y+1, z+1.
 

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