Literature DB >> 21581495

cis-Bis{1-[(4-nitro-phen-yl)diazen-yl]-2-naphtholato}dipyridine-nickel(II).

Lorenzo do Canto Visentin1, Carlos Alberto Lombardi Filgueiras, Jairo Bordinhão, Leonardo da Cunha Ferreira.   

Abstract

In the title compound, [Ni(C(16)H(10)N(3)O(3))(2)(C(5)H(5)N)(2)], the Ni(II) cation is in a distorted octa-hedral NiN(4)O(2) coordination by two independent bidentate 1-[(4-nitro-phen-yl)diazen-yl]-2-naph-thol-ate anions and two pyridine ligands. C-H⋯O inter-actions between aromatic rings and the O atoms of the nitro substituents build up a two-dimensional supra-molecular arrangement parallel to (100).

Entities:  

Year:  2008        PMID： 21581495      PMCID： PMC2967869          DOI： 10.1107/S1600536808040476

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For background on metal azo complexes, see: Carella et al. (2007 ▶); Kulikovska et al. (2007 ▶); Patnaik et al. (2007 ▶); Leng et al. (2001 ▶). For bond lengths, see: Abildgaard et al. (2006 ▶). For hydrogen bonds, see: Jeffrey & Saenger (1991 ▶).

Experimental

Crystal data

[Ni(C16H10N3O3)2(C5H5N)2] M = 801.45 Monoclinic, a = 11.719 (2) Å b = 18.885 (4) Å c = 16.922 (3) Å β = 93.04 (3)° V = 3740.0 (13) Å3 Z = 4 Mo Kα radiation μ = 0.58 mm−1 T = 295 (2) K 0.37 × 0.18 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.814, T max = 0.918 64998 measured reflections 6566 independent reflections 4859 reflections with I > 2σ(I) R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.090 S = 1.05 6566 reflections 514 parameters H-atom parameters constrained Δρmax = 0.23 e Å−3 Δρmin = −0.24 e Å−3 Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: PHICHI (Duisenberg et al., 2000 ▶); data reduction: EVALCCD (Duisenberg et al., 2003 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶) and WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040476/wm2206sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040476/wm2206Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Ni(C16H10N3O3)2(C5H5N)2]F(000) = 1656
Mr = 801.45Dx = 1.423 Mg m−3
Monoclinic, P21/cMelting point: 473 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 11.719 (2) ÅCell parameters from 217 reflections
b = 18.885 (4) Åθ = 1.0–27.5°
c = 16.922 (3) ŵ = 0.58 mm−1
β = 93.04 (3)°T = 295 K
V = 3740.0 (13) Å3Block, red
Z = 40.37 × 0.18 × 0.15 mm
Nonius KappaCCD diffractometer6566 independent reflections
Radiation source: fine-focus sealed tube4859 reflections with I > 2σ(I)
graphiteRint = 0.076
φ and ω scansθmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)h = −13→13
Tmin = 0.814, Tmax = 0.918k = −22→22
64998 measured reflectionsl = −20→20
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0357P)2 + 1.6025P] where P = (Fo2 + 2Fc2)/3
6566 reflections(Δ/σ)max < 0.001
514 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.24 e Å−3
Experimental. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)5.9841 (0.0107) x + 0.5948 (0.0176) y + 14.0605 (0.0119) z = 4.0378 (0.0057)* 0.0370 (0.0010) N1 * -0.0652 (0.0015) N2 * 0.0496 (0.0015) C1 * -0.0087 (0.0015) C2 * -0.0127 (0.0010) O1Rms deviation of fitted atoms = 0.0408- 0.4462 (0.0069) x + 8.8584 (0.0115) y + 14.9440 (0.0093) z = 1.2966 (0.0053)Angle to previous plane (with approximate e.s.d.) = 41.11 (0.07)* 0.0666 (0.0009) O1 * -0.0633 (0.0009) N1 * 0.0616 (0.0008) O4 * -0.0623 (0.0009) N8 * -0.0026 (0.0008) Ni1Rms deviation of fitted atoms = 0.05686.2807 (0.0104) x - 6.1779 (0.0201) y + 12.6704 (0.0108) z = 5.5919 (0.0111)Angle to previous plane (with approximate e.s.d.) = 59.14 (0.06)* -0.0118 (0.0011) O4 * 0.0423 (0.0016) C18 * -0.0623 (0.0015) C17 * 0.0507 (0.0015) N5 * -0.0189 (0.0010) N4Rms deviation of fitted atoms = 0.0418- 0.0859 (0.0070) x + 16.1355 (0.0106) y - 8.7731 (0.0106) z = 1.4081 (0.0053)Angle to previous plane (with approximate e.s.d.) = 46.54 (0.09)* 0.0058 (0.0009) O4 * 0.0056 (0.0010) N4 * 0.0063 (0.0009) O1 * 0.0060 (0.0009) N7 * -0.0236 (0.0008) Ni1Rms deviation of fitted atoms = 0.01186.5874 (0.0126) x + 14.2991 (0.0164) y - 6.1291 (0.0186) z = 6.0049 (0.0088)Angle to previous plane (with approximate e.s.d.) = 35.34 (0.09)* 0.0044 (0.0017) N7 * -0.0069 (0.0020) C33 * 0.0029 (0.0023) C34 * 0.0033 (0.0025) C35 * -0.0056 (0.0023) C36 * 0.0019 (0.0019) C37Rms deviation of fitted atoms = 0.00456.8092 (0.0117) x - 4.2913 (0.0191) y - 13.7284 (0.0134) z = 3.6963 (0.0099)Angle to previous plane (with approximate e.s.d.) = 65.50 (0.09)* 0.0087 (0.0016) N8 * -0.0004 (0.0019) C38 * -0.0074 (0.0021) C39 * 0.0071 (0.0020) C40 * 0.0011 (0.0019) C41 * -0.0092 (0.0018) C42Rms deviation of fitted atoms = 0.00677.6103 (0.0099) x - 1.0403 (0.0194) y + 12.2331 (0.0135) z = 7.5132 (0.0060)Angle to previous plane (with approximate e.s.d.) = 78.29 (0.07)* -0.0081 (0.0017) C27 * 0.0104 (0.0018) C28 * -0.0020 (0.0018) C29 * -0.0088 (0.0018) C30 * 0.0109 (0.0019) C31 * -0.0025 (0.0019) C32Rms deviation of fitted atoms = 0.00796.0882 (0.0095) x - 3.0287 (0.0105) y + 13.7154 (0.0112) z = 6.1985 (0.0098)Angle to previous plane (with approximate e.s.d.) = 10.66 (0.13)* 0.0072 (0.0020) C17 * -0.1226 (0.0020) C18 * 0.0188 (0.0022) C19 * 0.0637 (0.0024) C20 * 0.0353 (0.0026) C21 * -0.0368 (0.0028) C22 * -0.0666 (0.0033) C23 * -0.0092 (0.0031) C24 * 0.0452 (0.0026) C25 * 0.0652 (0.0024) C26Rms deviation of fitted atoms = 0.05746.0989 (0.0089) x - 1.3127 (0.0101) y + 13.9139 (0.0107) z = 3.6881 (0.0050)Angle to previous plane (with approximate e.s.d.) = 5.25 (0.11)* -0.0019 (0.0019) C1 * 0.0685 (0.0019) C2 * -0.0202 (0.0021) C3 * -0.0339 (0.0022) C4 * -0.0136 (0.0024) C5 * 0.0221 (0.0025) C6 * 0.0381 (0.0028) C7 * -0.0039 (0.0027) C8 * -0.0255 (0.0024) C9 * -0.0297 (0.0023) C10Rms deviation of fitted atoms = 0.03157.6507 (0.0101) x - 0.7993 (0.0215) y + 12.1938 (0.0139) z = 4.9408 (0.0114)Angle to previous plane (with approximate e.s.d.) = 9.47 (0.13)* 0.0100 (0.0017) C11 * -0.0050 (0.0019) C12 * -0.0055 (0.0021) C13 * 0.0110 (0.0019) C14 * -0.0058 (0.0018) C15 * -0.0048 (0.0018) C16Rms deviation of fitted atoms = 0.0075
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.
xyzUiso*/Ueq
Ni10.73654 (2)0.112500 (16)0.041889 (18)0.03358 (10)
N10.71063 (15)0.21142 (10)−0.02158 (11)0.0336 (4)
N20.63714 (16)0.25763 (10)0.00047 (11)0.0370 (5)
N31.0357 (2)0.33257 (17)−0.21680 (16)0.0701 (8)
N40.75644 (16)0.17270 (10)0.14908 (11)0.0379 (5)
N50.81962 (17)0.22968 (11)0.15104 (12)0.0401 (5)
N60.4055 (2)0.16963 (14)0.36697 (13)0.0531 (6)
N70.73012 (17)0.05551 (10)−0.06623 (12)0.0406 (5)
N80.74895 (17)0.01201 (10)0.09784 (12)0.0386 (5)
C10.54975 (19)0.23983 (13)0.04658 (13)0.0358 (5)
C20.51196 (19)0.16895 (14)0.06152 (14)0.0373 (6)
C30.4060 (2)0.16159 (16)0.10089 (15)0.0471 (6)
H30.37510.11660.10670.056*
C40.3506 (2)0.21795 (17)0.12949 (16)0.0543 (8)
H40.28440.21030.15610.065*
C50.3901 (2)0.28914 (16)0.12038 (15)0.0480 (7)
C60.3342 (3)0.3474 (2)0.15296 (18)0.0678 (9)
H60.26960.33980.18150.081*
C70.3728 (3)0.4148 (2)0.1435 (2)0.0803 (11)
H70.33560.45270.16620.096*
C80.4683 (3)0.42665 (18)0.0997 (2)0.0732 (10)
H80.49370.47270.09200.088*
C90.5259 (3)0.37042 (15)0.06765 (18)0.0577 (8)
H90.59040.37910.03940.069*
C100.4883 (2)0.30047 (14)0.07722 (14)0.0426 (6)
C110.78929 (19)0.24392 (12)−0.07322 (13)0.0340 (5)
C120.8024 (2)0.31680 (14)−0.07792 (16)0.0482 (7)
H120.75740.3463−0.04850.058*
C130.8815 (3)0.34579 (15)−0.12567 (17)0.0575 (8)
H130.89000.3947−0.12870.069*
C140.9481 (2)0.30173 (15)−0.16898 (15)0.0465 (7)
C150.9355 (2)0.22981 (14)−0.16720 (15)0.0451 (6)
H150.97980.2009−0.19780.054*
C160.8561 (2)0.20082 (13)−0.11915 (15)0.0415 (6)
H160.84700.1519−0.11740.050*
C170.9075 (2)0.23637 (13)0.10183 (14)0.0413 (6)
C180.9558 (2)0.17932 (14)0.05833 (15)0.0425 (6)
C191.0637 (2)0.19248 (16)0.02366 (17)0.0532 (7)
H191.10290.15480.00240.064*
C201.1091 (2)0.25816 (18)0.02127 (18)0.0605 (8)
H201.17710.2647−0.00370.073*
C211.0559 (2)0.31780 (17)0.05598 (17)0.0571 (8)
C221.0988 (3)0.3870 (2)0.0470 (2)0.0810 (11)
H221.16300.39410.01800.097*
C231.0472 (4)0.4438 (2)0.0802 (3)0.0974 (14)
H231.07560.48920.07340.117*
C240.9519 (4)0.43321 (19)0.1244 (3)0.0902 (12)
H240.91800.47170.14810.108*
C250.9069 (3)0.36590 (16)0.13346 (19)0.0663 (9)
H250.84240.35980.16240.080*
C260.9579 (2)0.30722 (15)0.09933 (16)0.0495 (7)
C270.6742 (2)0.17444 (13)0.20889 (13)0.0376 (6)
C280.6336 (2)0.23743 (13)0.24103 (15)0.0418 (6)
H280.66500.28050.22680.050*
C290.5478 (2)0.23611 (14)0.29330 (15)0.0449 (6)
H290.52020.27810.31380.054*
C300.5028 (2)0.17145 (14)0.31523 (14)0.0416 (6)
C310.5433 (2)0.10847 (14)0.28627 (14)0.0463 (6)
H310.51400.06540.30260.056*
C320.6281 (2)0.11035 (14)0.23263 (15)0.0466 (6)
H320.65470.06820.21200.056*
C330.6487 (2)0.06812 (15)−0.12249 (16)0.0511 (7)
H330.58970.0989−0.11150.061*
C340.6486 (3)0.03716 (19)−0.19646 (19)0.0736 (10)
H340.59130.0475−0.23490.088*
C350.7351 (3)−0.0094 (2)−0.2122 (2)0.0834 (12)
H350.7370−0.0310−0.26150.100*
C360.8178 (3)−0.02345 (18)−0.1546 (2)0.0731 (10)
H360.8763−0.0552−0.16390.088*
C370.8135 (2)0.00968 (14)−0.08311 (17)0.0519 (7)
H370.87070.0002−0.04430.062*
C380.8368 (2)−0.00533 (14)0.14751 (16)0.0485 (7)
H380.88930.02970.16270.058*
C390.8535 (3)−0.07288 (16)0.17741 (18)0.0595 (8)
H390.9154−0.08280.21230.071*
C400.7765 (3)−0.12535 (15)0.15457 (18)0.0580 (8)
H400.7864−0.17150.17290.070*
C410.6855 (2)−0.10789 (14)0.10441 (17)0.0512 (7)
H410.6321−0.14210.08840.061*
C420.6738 (2)−0.03930 (13)0.07789 (16)0.0444 (6)
H420.6107−0.02800.04460.053*
O10.56484 (13)0.11301 (9)0.04110 (10)0.0399 (4)
O21.0358 (3)0.39692 (16)−0.22459 (19)0.1256 (12)
O31.1043 (2)0.29343 (15)−0.24720 (15)0.0888 (8)
O40.90854 (14)0.11845 (9)0.04779 (10)0.0449 (4)
O50.3680 (2)0.11152 (12)0.38569 (14)0.0799 (7)
O60.36631 (19)0.22562 (12)0.38958 (14)0.0758 (7)
U11U22U33U12U13U23
Ni10.03349 (16)0.03100 (16)0.03668 (17)−0.00179 (13)0.00593 (12)−0.00190 (14)
N10.0334 (10)0.0355 (11)0.0326 (11)−0.0007 (9)0.0084 (8)−0.0021 (9)
N20.0360 (11)0.0394 (12)0.0358 (11)0.0018 (9)0.0035 (9)−0.0009 (9)
N30.0730 (18)0.082 (2)0.0574 (16)−0.0254 (16)0.0229 (14)0.0154 (15)
N40.0411 (11)0.0361 (11)0.0367 (11)−0.0049 (9)0.0021 (9)0.0001 (9)
N50.0453 (12)0.0389 (12)0.0354 (11)−0.0060 (10)−0.0040 (9)0.0009 (9)
N60.0605 (15)0.0575 (16)0.0422 (13)0.0017 (13)0.0103 (11)−0.0041 (12)
N70.0450 (12)0.0345 (11)0.0432 (12)−0.0056 (9)0.0103 (10)−0.0051 (10)
N80.0407 (11)0.0347 (11)0.0410 (12)0.0008 (9)0.0063 (9)−0.0002 (9)
C10.0346 (13)0.0434 (14)0.0299 (13)0.0023 (11)0.0045 (10)−0.0015 (11)
C20.0308 (12)0.0500 (15)0.0311 (13)0.0022 (11)0.0005 (10)−0.0028 (11)
C30.0313 (13)0.0617 (18)0.0488 (16)−0.0056 (12)0.0077 (11)0.0017 (14)
C40.0323 (14)0.089 (2)0.0428 (16)0.0034 (14)0.0072 (12)−0.0034 (15)
C50.0369 (14)0.0677 (19)0.0392 (15)0.0134 (13)0.0006 (11)−0.0089 (13)
C60.0507 (18)0.093 (3)0.060 (2)0.0191 (18)0.0077 (15)−0.0226 (19)
C70.074 (2)0.084 (3)0.083 (3)0.032 (2)0.004 (2)−0.036 (2)
C80.080 (2)0.057 (2)0.083 (2)0.0170 (17)0.0030 (19)−0.0207 (18)
C90.0619 (18)0.0523 (18)0.0594 (19)0.0119 (14)0.0090 (15)−0.0092 (14)
C100.0426 (14)0.0510 (16)0.0340 (14)0.0106 (12)−0.0011 (11)−0.0044 (12)
C110.0357 (13)0.0371 (13)0.0291 (12)−0.0040 (10)0.0005 (10)0.0022 (10)
C120.0582 (17)0.0404 (15)0.0473 (16)−0.0031 (12)0.0155 (13)−0.0014 (12)
C130.072 (2)0.0411 (16)0.0603 (19)−0.0136 (14)0.0173 (15)0.0090 (14)
C140.0456 (15)0.0587 (18)0.0358 (14)−0.0105 (13)0.0074 (12)0.0098 (13)
C150.0435 (15)0.0518 (17)0.0413 (15)0.0018 (12)0.0131 (12)0.0049 (12)
C160.0430 (14)0.0362 (14)0.0464 (15)−0.0019 (11)0.0128 (12)0.0032 (12)
C170.0412 (14)0.0465 (15)0.0353 (14)−0.0087 (12)−0.0053 (11)0.0041 (12)
C180.0353 (13)0.0508 (17)0.0409 (14)−0.0035 (12)−0.0032 (11)0.0084 (12)
C190.0363 (14)0.0658 (19)0.0575 (18)−0.0043 (13)0.0024 (13)0.0042 (15)
C200.0383 (15)0.087 (2)0.0555 (18)−0.0191 (16)−0.0039 (13)0.0154 (17)
C210.0522 (17)0.066 (2)0.0515 (17)−0.0233 (15)−0.0131 (14)0.0154 (15)
C220.074 (2)0.080 (3)0.087 (3)−0.040 (2)−0.0172 (19)0.027 (2)
C230.117 (4)0.056 (2)0.116 (4)−0.038 (2)−0.020 (3)0.020 (2)
C240.114 (3)0.050 (2)0.104 (3)−0.021 (2)−0.008 (3)−0.004 (2)
C250.081 (2)0.0481 (18)0.069 (2)−0.0153 (16)−0.0033 (17)−0.0007 (15)
C260.0538 (16)0.0490 (17)0.0442 (16)−0.0140 (13)−0.0131 (13)0.0053 (13)
C270.0435 (14)0.0403 (14)0.0287 (12)−0.0014 (11)−0.0010 (10)−0.0031 (11)
C280.0486 (15)0.0366 (14)0.0399 (15)−0.0065 (11)0.0010 (12)−0.0024 (11)
C290.0555 (16)0.0387 (15)0.0405 (15)0.0013 (12)0.0021 (12)−0.0106 (12)
C300.0461 (14)0.0480 (16)0.0310 (13)0.0009 (12)0.0032 (11)−0.0040 (12)
C310.0629 (17)0.0366 (14)0.0404 (14)−0.0010 (13)0.0132 (12)0.0038 (12)
C320.0624 (17)0.0366 (14)0.0420 (14)0.0016 (13)0.0129 (12)−0.0015 (12)
C330.0589 (17)0.0480 (17)0.0466 (16)−0.0088 (13)0.0054 (14)−0.0072 (13)
C340.080 (2)0.090 (3)0.0504 (19)−0.027 (2)−0.0005 (17)−0.0147 (18)
C350.099 (3)0.091 (3)0.064 (2)−0.031 (2)0.037 (2)−0.042 (2)
C360.072 (2)0.069 (2)0.082 (2)−0.0109 (18)0.037 (2)−0.032 (2)
C370.0527 (16)0.0437 (16)0.0614 (18)−0.0034 (13)0.0233 (14)−0.0109 (14)
C380.0496 (16)0.0451 (16)0.0505 (16)0.0002 (12)−0.0006 (13)−0.0016 (13)
C390.0621 (19)0.0571 (19)0.0584 (19)0.0098 (15)−0.0056 (15)0.0089 (15)
C400.074 (2)0.0377 (16)0.0638 (19)0.0050 (14)0.0153 (16)0.0099 (14)
C410.0599 (17)0.0389 (15)0.0557 (17)−0.0084 (13)0.0102 (14)0.0021 (13)
C420.0449 (15)0.0391 (15)0.0495 (16)−0.0038 (12)0.0060 (12)0.0010 (12)
O10.0348 (9)0.0402 (9)0.0453 (10)−0.0050 (8)0.0083 (7)−0.0032 (8)
O20.157 (3)0.083 (2)0.145 (3)−0.0318 (19)0.088 (2)0.0334 (19)
O30.0725 (16)0.114 (2)0.0840 (18)−0.0154 (15)0.0420 (14)0.0119 (16)
O40.0380 (9)0.0412 (10)0.0561 (11)−0.0026 (8)0.0067 (8)−0.0015 (9)
O50.0960 (17)0.0644 (15)0.0839 (16)−0.0114 (13)0.0483 (13)−0.0033 (13)
O60.0788 (15)0.0641 (14)0.0879 (17)0.0151 (12)0.0367 (13)−0.0108 (12)
Ni1—N12.168 (2)C16—H160.9300
Ni1—N42.143 (2)C17—C181.438 (4)
Ni1—N72.121 (2)C17—C261.464 (3)
Ni1—N82.122 (2)C18—O41.284 (3)
Ni1—O12.0116 (16)C18—C191.443 (3)
Ni1—O42.0161 (17)C19—C201.351 (4)
N1—N21.295 (3)C19—H190.9300
N1—C111.441 (3)C20—C211.429 (4)
N2—C11.362 (3)C20—H200.9300
N3—O21.222 (4)C21—C261.409 (4)
N3—O31.225 (4)C22—C231.366 (5)
N3—C141.462 (3)C22—C211.412 (4)
N4—N51.306 (3)C22—H220.9300
N4—C271.434 (3)C23—C241.390 (6)
N5—C171.364 (3)C23—H230.9300
N6—O51.230 (3)C24—C251.388 (4)
N6—C301.474 (3)C24—H240.9300
N7—C331.333 (3)C25—C261.398 (4)
N7—C371.348 (3)C25—H250.9300
N8—C381.335 (3)C27—C321.394 (3)
N8—C421.341 (3)C27—C281.402 (3)
C1—C21.437 (3)C28—C291.374 (3)
C1—C101.462 (3)C28—H280.9300
C2—O11.281 (3)C29—C301.389 (3)
C2—C31.447 (3)C29—H290.9300
C3—C41.350 (4)C30—C311.380 (3)
C3—H30.9300C31—C321.381 (3)
C4—C51.433 (4)C31—H310.9300
C4—H40.9300C32—H320.9300
C5—C61.409 (4)C33—C341.381 (4)
C5—C101.412 (4)C33—H330.9300
C6—C71.363 (5)C34—C351.379 (5)
C6—H60.9300C34—H340.9300
C7—H70.9300C35—C361.363 (5)
C8—C91.384 (4)C35—H350.9300
C8—C71.393 (5)C36—C371.365 (4)
C8—H80.9300C36—H360.9300
C9—C101.405 (4)C37—H370.9300
C9—H90.9300C38—C391.382 (4)
C11—C121.388 (3)C38—H380.9300
C11—C161.394 (3)C39—C401.381 (4)
C12—C131.375 (4)C39—H390.9300
C12—H120.9300C40—C411.368 (4)
C13—C141.378 (4)C40—H400.9300
C13—H130.9300C41—C421.375 (4)
C14—C151.367 (4)C41—H410.9300
C15—C161.382 (3)C42—H420.9300
C15—H150.9300O6—N61.222 (3)
N1—N2—C1122.0 (2)C8—C7—H7120.2
N2—C1—C2125.4 (2)C8—C9—C10120.9 (3)
N2—C1—C10114.1 (2)C8—C9—H9119.5
N2—N1—C11110.14 (18)C10—C9—H9119.5
N2—N1—Ni1121.05 (14)C9—C10—C5118.1 (2)
N4—Ni1—N188.18 (7)C9—C10—C1122.2 (2)
N4—N5—C17120.4 (2)C5—C10—C1119.7 (2)
N5—N4—C27111.37 (19)C12—C11—C16118.7 (2)
N5—N4—Ni1119.66 (15)C12—C11—N1122.3 (2)
N5—C17—C18125.0 (2)C16—C11—N1119.0 (2)
N5—C17—C26114.9 (2)C13—C12—C11120.6 (3)
N7—Ni1—N190.70 (8)C13—C12—H12119.7
N7—Ni1—N4175.45 (7)C11—C12—H12119.7
N7—Ni1—N885.96 (8)C12—C13—C14119.4 (3)
N7—C37—C36122.9 (3)C12—C13—H13120.3
N7—C37—H37118.5C14—C13—H13120.3
N7—C33—C34122.5 (3)C15—C14—C13121.6 (2)
N7—C33—H33118.7C15—C14—N3119.2 (3)
N8—C42—C41123.1 (3)C13—C14—N3119.2 (3)
N8—C42—H42118.5C14—C15—C16118.9 (2)
N8—C38—C39123.1 (3)C14—C15—H15120.5
N8—C38—H38118.5C16—C15—H15120.5
N8—Ni1—N1174.80 (8)C15—C16—C11120.8 (2)
N8—Ni1—N495.45 (8)C15—C16—H16119.6
O1—Ni1—N493.84 (7)C11—C16—H16119.6
O1—Ni1—O4175.75 (7)C18—C17—C26120.0 (2)
O1—Ni1—N790.40 (8)C17—C18—C19117.1 (2)
O1—Ni1—N892.99 (7)C20—C19—C18121.7 (3)
O1—Ni1—N183.04 (7)C20—C19—H19119.2
O1—C2—C1124.2 (2)C18—C19—H19119.2
O1—C2—C3119.0 (2)C19—C20—C21122.0 (3)
O2—N3—O3123.4 (3)C19—C20—H20119.0
O2—N3—C14117.4 (3)C21—C20—H20119.0
O3—N3—C14119.2 (3)C26—C21—C22119.5 (3)
O4—Ni1—N482.23 (8)C26—C21—C20119.2 (3)
O4—Ni1—N793.47 (8)C22—C21—C20121.3 (3)
O4—Ni1—N889.03 (7)C25—C26—C21118.7 (3)
O4—Ni1—N195.16 (7)C25—C26—C17122.0 (3)
O4—C18—C17124.3 (2)C21—C26—C17119.1 (3)
O4—C18—C19118.6 (2)C32—C27—C28118.7 (2)
O5—N6—C30118.2 (2)C32—C27—N4118.0 (2)
O6—N6—O5123.1 (2)C28—C27—N4123.2 (2)
O6—N6—C30118.8 (2)C29—C28—C27120.6 (2)
C11—N1—Ni1126.17 (14)C29—C28—H28119.7
C27—N4—Ni1124.23 (15)C27—C28—H28119.7
C9—C8—C7120.5 (3)C28—C29—C30119.3 (2)
C9—C8—H8119.7C28—C29—H29120.4
C7—C8—H8119.7C30—C29—H29120.4
C23—C22—C21120.9 (4)C31—C30—C29121.3 (2)
C23—C22—H22119.5C31—C30—N6118.8 (2)
C21—C22—H22119.5C29—C30—N6119.7 (2)
C22—C23—C24119.7 (3)C30—C31—C32119.0 (2)
C22—C23—H23120.2C30—C31—H31120.5
C24—C23—H23120.2C32—C31—H31120.5
C25—C24—C23120.8 (4)C31—C32—C27121.0 (2)
C25—C24—H24119.6C31—C32—H32119.5
C23—C24—H24119.6C27—C32—H32119.5
C24—C25—C26120.4 (3)C34—C33—H33118.7
C24—C25—H25119.8C35—C34—C33118.6 (3)
C26—C25—H25119.8C35—C34—H34120.7
C33—N7—C37117.6 (2)C33—C34—H34120.7
C33—N7—Ni1121.11 (17)C36—C35—C34119.2 (3)
C37—N7—Ni1121.06 (19)C36—C35—H35120.4
C38—N8—C42117.1 (2)C34—C35—H35120.4
C38—N8—Ni1122.17 (17)C35—C36—C37119.1 (3)
C42—N8—Ni1120.36 (17)C35—C36—H36120.5
C2—C1—C10120.4 (2)C37—C36—H36120.5
C1—C2—C3116.8 (2)C36—C37—H37118.5
C4—C3—C2122.0 (3)C39—C38—H38118.5
C4—C3—H3119.0C40—C39—C38118.8 (3)
C2—C3—H3119.0C40—C39—H39120.6
C3—C4—C5122.5 (2)C38—C39—H39120.6
C3—C4—H4118.7C41—C40—C39118.5 (3)
C5—C4—H4118.7C41—C40—H40120.8
C6—C5—C10119.5 (3)C39—C40—H40120.8
C6—C5—C4122.1 (3)C40—C41—C42119.4 (3)
C10—C5—C4118.3 (2)C40—C41—H41120.3
C7—C6—C5121.3 (3)C42—C41—H41120.3
C7—C6—H6119.3C41—C42—H42118.5
C5—C6—H6119.3C2—O1—Ni1120.00 (14)
C6—C7—C8119.5 (3)C18—O4—Ni1118.64 (15)
C6—C7—H7120.2
C21—C22—C23—C240.8 (6)O2—N3—C14—C13−9.6 (4)
C22—C23—C24—C25−1.6 (6)O3—N3—C14—C13170.8 (3)
C23—C24—C25—C261.1 (6)C13—C14—C15—C16−1.7 (4)
O1—Ni1—N1—N243.27 (17)N3—C14—C15—C16177.1 (2)
O4—Ni1—N1—N2−132.86 (17)C14—C15—C16—C110.1 (4)
N7—Ni1—N1—N2133.59 (17)C12—C11—C16—C151.4 (4)
N4—Ni1—N1—N2−50.82 (17)N1—C11—C16—C15−177.6 (2)
O1—Ni1—N1—C11−156.98 (18)N4—N5—C17—C18−14.8 (4)
O4—Ni1—N1—C1126.89 (18)N4—N5—C17—C26169.2 (2)
N7—Ni1—N1—C11−66.66 (18)N5—C17—C18—O414.6 (4)
N4—Ni1—N1—C11108.92 (18)C26—C17—C18—O4−169.7 (2)
C11—N1—N2—C1176.8 (2)N5—C17—C18—C19−166.3 (2)
Ni1—N1—N2—C1−20.5 (3)C26—C17—C18—C199.4 (3)
O1—Ni1—N4—N5−127.58 (17)O4—C18—C19—C20169.1 (3)
O4—Ni1—N4—N550.77 (17)C17—C18—C19—C20−10.0 (4)
N8—Ni1—N4—N5139.04 (17)C18—C19—C20—C212.9 (4)
N1—Ni1—N4—N5−44.68 (17)C23—C22—C21—C260.5 (5)
O1—Ni1—N4—C2725.88 (19)C23—C22—C21—C20179.8 (3)
O4—Ni1—N4—C27−155.77 (19)C19—C20—C21—C265.0 (4)
N8—Ni1—N4—C27−67.50 (19)C19—C20—C21—C22−174.3 (3)
N1—Ni1—N4—C27108.78 (18)C24—C25—C26—C210.3 (5)
C27—N4—N5—C17176.1 (2)C24—C25—C26—C17−174.7 (3)
Ni1—N4—N5—C17−27.2 (3)C22—C21—C26—C25−1.1 (4)
O1—Ni1—N7—C3336.6 (2)C20—C21—C26—C25179.6 (3)
O4—Ni1—N7—C33−141.64 (19)C22—C21—C26—C17174.0 (3)
N8—Ni1—N7—C33129.6 (2)C20—C21—C26—C17−5.3 (4)
N1—Ni1—N7—C33−46.4 (2)N5—C17—C26—C25−10.9 (4)
O1—Ni1—N7—C37−149.05 (19)C18—C17—C26—C25172.9 (3)
O4—Ni1—N7—C3732.70 (19)N5—C17—C26—C21174.1 (2)
N8—Ni1—N7—C37−56.08 (19)C18—C17—C26—C21−2.0 (4)
N1—Ni1—N7—C37127.91 (19)N5—N4—C27—C32−158.6 (2)
O1—Ni1—N8—C38−147.84 (19)Ni1—N4—C27—C3246.0 (3)
O4—Ni1—N8—C3828.4 (2)N5—N4—C27—C2825.2 (3)
N7—Ni1—N8—C38122.0 (2)Ni1—N4—C27—C28−130.2 (2)
N4—Ni1—N8—C38−53.7 (2)C32—C27—C28—C29−1.7 (4)
O1—Ni1—N8—C4239.14 (19)N4—C27—C28—C29174.5 (2)
O4—Ni1—N8—C42−144.60 (19)C27—C28—C29—C301.2 (4)
N7—Ni1—N8—C42−51.05 (19)C28—C29—C30—C310.7 (4)
N4—Ni1—N8—C42133.29 (18)C28—C29—C30—N6−175.9 (2)
N1—N2—C1—C2−14.7 (4)O6—N6—C30—C31−176.6 (2)
N1—N2—C1—C10169.5 (2)O5—N6—C30—C313.7 (4)
N2—C1—C2—O19.0 (4)O6—N6—C30—C290.0 (4)
C10—C1—C2—O1−175.5 (2)O5—N6—C30—C29−179.6 (3)
N2—C1—C2—C3−169.8 (2)C29—C30—C31—C32−1.9 (4)
C10—C1—C2—C35.7 (3)N6—C30—C31—C32174.7 (2)
O1—C2—C3—C4174.7 (2)C30—C31—C32—C271.3 (4)
C1—C2—C3—C4−6.4 (4)C28—C27—C32—C310.5 (4)
C2—C3—C4—C52.4 (4)N4—C27—C32—C31−175.9 (2)
C3—C4—C5—C6−177.6 (3)C37—N7—C33—C34−1.2 (4)
C3—C4—C5—C102.4 (4)Ni1—N7—C33—C34173.4 (2)
C10—C5—C6—C70.2 (4)N7—C33—C34—C351.0 (5)
C4—C5—C6—C7−179.9 (3)C33—C34—C35—C360.0 (5)
C5—C6—C7—C81.1 (5)C34—C35—C36—C37−0.8 (5)
C9—C8—C7—C6−1.7 (5)C33—N7—C37—C360.3 (4)
C7—C8—C9—C101.1 (5)Ni1—N7—C37—C36−174.2 (2)
C8—C9—C10—C50.1 (4)C35—C36—C37—N70.7 (5)
C8—C9—C10—C1−177.7 (3)C42—N8—C38—C391.0 (4)
C6—C5—C10—C9−0.8 (4)Ni1—N8—C38—C39−172.3 (2)
C4—C5—C10—C9179.3 (2)N8—C38—C39—C400.6 (4)
C6—C5—C10—C1177.1 (2)C38—C39—C40—C41−1.3 (4)
C4—C5—C10—C1−2.9 (4)C39—C40—C41—C420.5 (4)
N2—C1—C10—C9−7.5 (4)C38—N8—C42—C41−1.8 (4)
C2—C1—C10—C9176.5 (2)Ni1—N8—C42—C41171.5 (2)
N2—C1—C10—C5174.8 (2)C40—C41—C42—N81.1 (4)
C2—C1—C10—C5−1.2 (3)C1—C2—O1—Ni134.0 (3)
N2—N1—C11—C1217.2 (3)C3—C2—O1—Ni1−147.22 (18)
Ni1—N1—C11—C12−144.4 (2)N7—Ni1—O1—C2−138.84 (17)
N2—N1—C11—C16−163.9 (2)N8—Ni1—O1—C2135.18 (17)
Ni1—N1—C11—C1634.5 (3)N4—Ni1—O1—C239.51 (18)
C16—C11—C12—C13−1.4 (4)N1—Ni1—O1—C2−48.18 (17)
N1—C11—C12—C13177.5 (2)C17—C18—O4—Ni130.8 (3)
C11—C12—C13—C14−0.1 (4)C19—C18—O4—Ni1−148.24 (19)
C12—C13—C14—C151.7 (4)N7—Ni1—O4—C18128.08 (18)
C12—C13—C14—N3−177.1 (3)N8—Ni1—O4—C18−146.03 (18)
O2—N3—C14—C15171.5 (3)N4—Ni1—O4—C18−50.39 (18)
O3—N3—C14—C15−8.0 (4)N1—Ni1—O4—C1837.06 (18)
D—H···AD—HH···AD···AD—H···A
C36—H36···O2i0.932.383.124 (5)137
C41—H41···O6ii0.932.533.205 (4)130
Table 1

Selected bond lengths (Å)

Ni1—N12.168 (2)
Ni1—N42.143 (2)
Ni1—N72.121 (2)
Ni1—N82.122 (2)
Ni1—O12.0116 (16)
Ni1—O42.0161 (17)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C36—H36⋯O2i0.932.383.124 (5)137
C41—H41⋯O6ii0.932.533.205 (4)130

Symmetry codes: (i) ; (ii) .

  2 in total

1.  Photoregulation of drug release in azo-dextran nanogels.

Authors:  Satyakam Patnaik; Ashwani K Sharma; B S Garg; R P Gandhi; K C Gupta
Journal:  Int J Pharm       Date:  2007-05-13       Impact factor: 5.875

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290
  2 in total

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