Literature DB >> 26029419

Crystal structure of a binuclear nickel(II) complex constructed of 1H-imidazo[4,5-f][1,10]phenanthroline and doubly deprotonated benzene-1,3,5-tri-carb-oxy-lic acid.

Ying Lv1, Xiang-Rong Hao1.   

Abstract

The title complex, [Ni2(C9H4O6)2(C13H8N4)2(H2O)4]·2H2O, bis-(μ-5-carb-oxy-benzene-1,3-di-carboxyl-ato-κ(2) O (1):O (1'))bis-[di-aqua(1H-imidazo[4,5-f][1,10]phenanthroline-κ(2) N (7),N (8))nickel(II)] di-hydrate, was obtained under solvothermal conditions by the reaction of benzene-1,3,5-tricarboxylic acid (H3BTC) with Ni(NO3)2 in the presence of 1H-imidazo[4,5-f][1,10]phenanthroline (IP). The crystal has triclinic (P-1) symmetry with a centrosymmetric binuclear nickel(II) cluster. The Ni(II) atom is coordinated by two N atoms from a chelating 1H-imidazo[4,5-f][1,10]phenanthroline ligand, two carboxyl-ate O atoms from two 5-carb-oxy-benzene-1,3-di-carboxyl-ate ligands and two water mol-ecules in a slightly distorted octa-hedral geometry. Two carboxyl-ate groups bridge two Ni(II) cations, forming the binuclear complex. Extensive N-H⋯O, O-H⋯O and O-H⋯N hydrogen bonding is present in the crystal structure, forming a three-dimensional supermolecular framework. Weak π-π stacking is observed between parallel HBTC(2-) and IP ring systems, the face-to-face separation being 3.695 (2) Å.

Entities:  

Keywords:  1H-imidazo[4,5-f][1,10]phenanthroline; benzene-1,3,5-tri­carboxyl­ic acid; binuclear cluster; crystal structure; hydrogen bonding; nickel(II) complex; π–π stacking

Year:  2015        PMID： 26029419      PMCID： PMC4438790          DOI： 10.1107/S205698901500420X

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


Related literature

For general background, see: Stephenson et al. (2008 ▸). For details of the synthesis, see: Liu et al. (2009 ▸); Wu et al. (1997 ▸); Yang et al. (2010 ▸); Che et al. (2013 ▸).

Experimental

Crystal data

[Ni2(C9H4O6)2(C13H8N4)2(H2O)4]·2H2O M = 1082.22 Triclinic, a = 8.581 (5) Å b = 9.032 (5) Å c = 14.278 (5) Å α = 82.222 (5)° β = 87.729 (5)° γ = 73.117 (5)° V = 1049.2 (9) Å3 Z = 1 Mo Kα radiation μ = 0.99 mm−1 T = 293 K 0.28 × 0.16 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T min = 0.805, T max = 0.867 5594 measured reflections 3851 independent reflections 3050 reflections with I > 2σ(I) R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.031 wR(F 2) = 0.072 S = 0.95 3851 reflections 325 parameters H-atom parameters constrained Δρmax = 0.30 e Å−3 Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: DIAMOND (Brandenburg & Putz, 1999 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸). Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S205698901500420X/zp2016sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901500420X/zp2016Isup2.hkl Click here for additional data file. x y z . DOI: 10.1107/S205698901500420X/zp2016fig1.tif The mol­ecular structure of the title compound, showing 30% probability displacement ellipsoids with the atom numbering. H atoms have been omitted for clarity. [Symmetry code: (i) −x + 1, −y + 1, −z + 1.] Click here for additional data file. a . DOI: 10.1107/S205698901500420X/zp2016fig2.tif A packing view of the three-dimensional supermolecular framework of the title compound viewed along the a axis. CCDC reference: 1051597 Additional supporting information: crystallographic information; 3D view; checkCIF report
[Ni2(C9H4O6)2(C13H8N4)2(H2O)4]·2H2OZ = 1
Mr = 1082.22F(000) = 556
Triclinic, P1Dx = 1.713 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 8.581 (5) ÅCell parameters from 2586 reflections
b = 9.032 (5) Åθ = 3.6–24.9°
c = 14.278 (5) ŵ = 0.99 mm−1
α = 82.222 (5)°T = 293 K
β = 87.729 (5)°Block, yellow-green
γ = 73.117 (5)°0.28 × 0.16 × 0.15 mm
V = 1049.2 (9) Å3
Bruker APEXII CCD diffractometer3851 independent reflections
Radiation source: fine-focus sealed tube3050 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
phi and ω scansθmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)h = −6→10
Tmin = 0.805, Tmax = 0.867k = −10→10
5594 measured reflectionsl = −16→17
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H-atom parameters constrained
S = 0.95w = 1/[σ2(Fo2) + (0.0333P)2] where P = (Fo2 + 2Fc2)/3
3851 reflections(Δ/σ)max = 0.001
325 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.42 e Å−3
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C10.6312 (3)0.3200 (3)0.81421 (15)0.0288 (6)
H10.54730.41270.81240.035*
C20.6567 (3)0.2172 (3)0.89778 (16)0.0338 (6)
H20.59120.24130.95030.041*
C30.7796 (3)0.0801 (3)0.90156 (16)0.0310 (6)
H30.79760.00920.95650.037*
C40.8778 (3)0.0478 (3)0.82195 (15)0.0227 (5)
C50.8443 (3)0.1596 (2)0.74049 (15)0.0209 (5)
C60.9472 (3)0.1389 (2)0.65729 (15)0.0207 (5)
C71.0812 (3)0.0055 (3)0.65371 (15)0.0231 (5)
C81.1781 (3)−0.0002 (3)0.57196 (16)0.0270 (5)
H81.2676−0.08610.56640.032*
C91.1399 (3)0.1215 (3)0.50060 (16)0.0280 (6)
H91.20380.11900.44640.034*
C101.0050 (3)0.2493 (3)0.50942 (15)0.0258 (5)
H100.98110.33150.46050.031*
C111.1089 (3)−0.1101 (3)0.73572 (15)0.0252 (5)
C121.0117 (3)−0.0873 (3)0.81472 (15)0.0243 (5)
C131.2023 (3)−0.3077 (3)0.83840 (17)0.0369 (6)
H131.2656−0.40310.86820.044*
C140.5942 (3)0.6540 (2)0.43305 (15)0.0220 (5)
C150.6305 (3)0.7419 (3)0.34261 (15)0.0212 (5)
C160.7606 (3)0.6785 (3)0.28582 (15)0.0234 (5)
H160.83260.58140.30610.028*
C170.7849 (3)0.7588 (3)0.19821 (15)0.0223 (5)
C180.6787 (3)0.9059 (3)0.17046 (16)0.0264 (5)
H180.69330.96010.11220.032*
C190.5521 (3)0.9727 (3)0.22814 (15)0.0243 (5)
C200.5259 (3)0.8897 (3)0.31353 (15)0.0249 (5)
H200.43840.93290.35150.030*
C220.9187 (3)0.6874 (3)0.13265 (15)0.0240 (5)
C230.4356 (3)1.1296 (3)0.19953 (17)0.0288 (6)
Ni10.70279 (4)0.43502 (3)0.609962 (19)0.02230 (10)
N10.7200 (2)0.2927 (2)0.73743 (12)0.0229 (4)
N20.9089 (2)0.2582 (2)0.58513 (12)0.0217 (4)
N31.2298 (2)−0.2516 (2)0.75156 (13)0.0329 (5)
N41.0757 (2)−0.2163 (2)0.88009 (13)0.0315 (5)
H41.0409−0.23410.93660.038*
O10.83799 (18)0.55829 (17)0.66524 (10)0.0274 (4)
H1WA0.89740.51750.71620.041*
H1WB0.77040.62880.69030.041*
O20.48839 (19)0.60135 (19)0.63947 (11)0.0368 (4)
H2WA0.42260.66110.67850.055*
H2WB0.43060.62950.58650.055*
O30.71191 (18)0.56435 (17)0.48112 (10)0.0257 (4)
O40.44422 (18)0.67849 (17)0.45611 (10)0.0249 (4)
O51.0320 (2)0.57271 (19)0.16548 (11)0.0346 (4)
O60.9071 (2)0.74669 (19)0.04712 (11)0.0365 (4)
O70.4671 (2)1.19600 (19)0.11669 (12)0.0474 (5)
H7O0.38281.26790.09560.071*
O80.3214 (2)1.18626 (19)0.24846 (12)0.0436 (5)
O90.7523 (2)0.56589 (19)0.96006 (11)0.0404 (5)
H9WA0.82630.55050.91680.061*
H9WB0.77620.62950.99330.061*
U11U22U33U12U13U23
C10.0238 (13)0.0318 (14)0.0252 (13)−0.0005 (11)0.0062 (11)−0.0021 (10)
C20.0336 (15)0.0396 (15)0.0225 (12)−0.0044 (12)0.0105 (11)−0.0014 (11)
C30.0342 (15)0.0327 (14)0.0205 (12)−0.0051 (12)0.0044 (11)0.0044 (10)
C40.0225 (12)0.0254 (12)0.0193 (11)−0.0073 (10)0.0023 (10)0.0007 (9)
C50.0202 (12)0.0238 (12)0.0181 (11)−0.0062 (10)0.0009 (10)−0.0007 (9)
C60.0190 (12)0.0242 (12)0.0186 (11)−0.0064 (10)0.0004 (9)−0.0010 (9)
C70.0211 (12)0.0260 (12)0.0216 (12)−0.0066 (10)0.0024 (10)−0.0027 (10)
C80.0240 (13)0.0257 (13)0.0286 (13)−0.0039 (11)0.0050 (11)−0.0028 (10)
C90.0266 (13)0.0334 (14)0.0217 (12)−0.0068 (11)0.0088 (10)−0.0021 (10)
C100.0276 (13)0.0297 (13)0.0192 (11)−0.0090 (11)0.0029 (10)0.0012 (10)
C110.0252 (13)0.0224 (12)0.0252 (12)−0.0040 (11)0.0023 (11)−0.0001 (10)
C120.0249 (13)0.0258 (12)0.0201 (11)−0.0061 (11)0.0023 (10)0.0009 (10)
C130.0355 (15)0.0277 (14)0.0354 (15)0.0038 (12)0.0040 (12)0.0084 (11)
C140.0252 (13)0.0221 (12)0.0179 (11)−0.0054 (11)0.0030 (10)−0.0034 (9)
C150.0205 (12)0.0250 (12)0.0171 (11)−0.0063 (10)0.0003 (10)0.0005 (9)
C160.0212 (12)0.0223 (12)0.0224 (12)−0.0016 (10)−0.0021 (10)0.0024 (9)
C170.0197 (12)0.0258 (12)0.0198 (11)−0.0051 (10)0.0002 (10)0.0003 (9)
C180.0273 (13)0.0277 (13)0.0208 (12)−0.0062 (11)0.0017 (10)0.0037 (10)
C190.0229 (13)0.0240 (12)0.0235 (12)−0.0046 (11)−0.0003 (10)0.0013 (10)
C200.0214 (12)0.0286 (13)0.0228 (12)−0.0045 (11)0.0051 (10)−0.0041 (10)
C220.0237 (13)0.0253 (13)0.0224 (12)−0.0071 (11)0.0016 (10)−0.0010 (10)
C230.0291 (14)0.0255 (13)0.0290 (13)−0.0050 (11)−0.0001 (12)−0.0003 (11)
Ni10.01924 (16)0.02540 (17)0.01782 (16)−0.00195 (13)0.00227 (12)0.00200 (12)
N10.0193 (10)0.0253 (10)0.0215 (10)−0.0036 (9)0.0017 (8)−0.0006 (8)
N20.0219 (10)0.0243 (10)0.0166 (9)−0.0055 (9)0.0021 (8)0.0017 (8)
N30.0295 (12)0.0291 (11)0.0283 (11)0.0053 (10)0.0070 (9)0.0043 (9)
N40.0333 (12)0.0313 (12)0.0214 (10)−0.0019 (10)0.0070 (9)0.0077 (9)
O10.0260 (9)0.0286 (9)0.0230 (8)−0.0014 (7)−0.0001 (7)−0.0022 (7)
O20.0285 (10)0.0466 (11)0.0211 (9)0.0106 (8)0.0009 (7)−0.0027 (8)
O30.0202 (8)0.0312 (9)0.0202 (8)−0.0030 (7)0.0009 (7)0.0065 (7)
O40.0200 (8)0.0314 (9)0.0201 (8)−0.0044 (7)0.0038 (7)−0.0001 (7)
O50.0287 (10)0.0391 (10)0.0238 (9)0.0074 (8)0.0002 (7)0.0006 (8)
O60.0357 (10)0.0424 (11)0.0201 (9)0.0012 (9)0.0069 (8)0.0063 (8)
O70.0398 (11)0.0397 (11)0.0407 (11)0.0114 (9)0.0098 (9)0.0172 (9)
O80.0469 (12)0.0290 (10)0.0425 (11)0.0061 (9)0.0138 (10)−0.0032 (8)
O90.0411 (11)0.0382 (10)0.0320 (10)0.0021 (9)0.0049 (8)−0.0016 (8)
C1—N11.319 (3)C15—C161.384 (3)
C1—C21.392 (3)C15—C201.394 (3)
C1—H10.9300C16—C171.399 (3)
C2—C31.370 (3)C16—H160.9300
C2—H20.9300C17—C181.391 (3)
C3—C41.399 (3)C17—C221.503 (3)
C3—H30.9300C18—C191.381 (3)
C4—C51.413 (3)C18—H180.9300
C4—C121.425 (3)C19—C201.388 (3)
C5—N11.353 (3)C19—C231.492 (3)
C5—C61.451 (3)C20—H200.9300
C6—N21.361 (3)C22—O51.248 (3)
C6—C71.408 (3)C22—O61.261 (3)
C7—C81.404 (3)C23—O81.209 (3)
C7—C111.437 (3)C23—O71.307 (3)
C8—C91.367 (3)Ni1—O32.0531 (16)
C8—H80.9300Ni1—N12.0652 (19)
C9—C101.392 (3)Ni1—N22.066 (2)
C9—H90.9300Ni1—O12.0662 (17)
C10—N21.330 (3)Ni1—O22.0794 (18)
C10—H100.9300Ni1—O4i2.1540 (17)
C11—C121.378 (3)N4—H40.8600
C11—N31.390 (3)O1—H1WA0.8794
C12—N41.380 (3)O1—H1WB0.8376
C13—N31.314 (3)O2—H2WA0.8944
C13—N41.333 (3)O2—H2WB0.8873
C13—H130.9300O4—Ni1i2.1540 (17)
C14—O31.255 (3)O7—H7O0.8528
C14—O41.279 (3)O9—H9WA0.8627
C14—C151.493 (3)O9—H9WB0.8651
N1—C1—C2123.3 (2)C19—C18—C17121.0 (2)
N1—C1—H1118.3C19—C18—H18119.5
C2—C1—H1118.3C17—C18—H18119.5
C3—C2—C1119.0 (2)C18—C19—C20119.7 (2)
C3—C2—H2120.5C18—C19—C23122.0 (2)
C1—C2—H2120.5C20—C19—C23118.2 (2)
C2—C3—C4119.3 (2)C19—C20—C15120.2 (2)
C2—C3—H3120.3C19—C20—H20119.9
C4—C3—H3120.3C15—C20—H20119.9
C3—C4—C5117.8 (2)O5—C22—O6124.3 (2)
C3—C4—C12126.4 (2)O5—C22—C17118.4 (2)
C5—C4—C12115.84 (19)O6—C22—C17117.2 (2)
N1—C5—C4122.0 (2)O8—C23—O7124.1 (2)
N1—C5—C6117.03 (19)O8—C23—C19122.2 (2)
C4—C5—C6120.9 (2)O7—C23—C19113.7 (2)
N2—C6—C7122.7 (2)O3—Ni1—N1173.78 (7)
N2—C6—C5115.78 (19)O3—Ni1—N294.05 (7)
C7—C6—C5121.52 (19)N1—Ni1—N280.10 (7)
C8—C7—C6117.2 (2)O3—Ni1—O188.33 (7)
C8—C7—C11126.1 (2)N1—Ni1—O189.79 (7)
C6—C7—C11116.7 (2)N2—Ni1—O192.10 (8)
C9—C8—C7119.5 (2)O3—Ni1—O289.01 (6)
C9—C8—H8120.2N1—Ni1—O296.93 (7)
C7—C8—H8120.2N2—Ni1—O2176.09 (7)
C8—C9—C10119.8 (2)O1—Ni1—O290.43 (8)
C8—C9—H9120.1O3—Ni1—O4i87.63 (6)
C10—C9—H9120.1N1—Ni1—O4i94.41 (7)
N2—C10—C9122.6 (2)N2—Ni1—O4i89.96 (8)
N2—C10—H10118.7O1—Ni1—O4i175.58 (6)
C9—C10—H10118.7O2—Ni1—O4i87.72 (8)
C12—C11—N3109.89 (19)C1—N1—C5118.49 (19)
C12—C11—C7121.0 (2)C1—N1—Ni1128.11 (16)
N3—C11—C7129.1 (2)C5—N1—Ni1113.32 (14)
C11—C12—N4105.6 (2)C10—N2—C6118.2 (2)
C11—C12—C4123.9 (2)C10—N2—Ni1128.14 (16)
N4—C12—C4130.4 (2)C6—N2—Ni1113.64 (14)
N3—C13—N4114.2 (2)C13—N3—C11103.84 (19)
N3—C13—H13122.9C13—N4—C12106.45 (19)
N4—C13—H13122.9C13—N4—H4126.8
O3—C14—O4125.1 (2)C12—N4—H4126.8
O3—C14—C15118.1 (2)Ni1—O1—H1WA120.3
O4—C14—C15116.79 (19)Ni1—O1—H1WB105.6
C16—C15—C20119.6 (2)H1WA—O1—H1WB96.1
C16—C15—C14121.87 (19)Ni1—O2—H2WA152.1
C20—C15—C14118.51 (19)Ni1—O2—H2WB106.7
C15—C16—C17120.7 (2)H2WA—O2—H2WB101.2
C15—C16—H16119.7C14—O3—Ni1127.43 (14)
C17—C16—H16119.7C14—O4—Ni1i119.27 (14)
C18—C17—C16118.7 (2)C23—O7—H7O109.8
C18—C17—C22119.7 (2)H9WA—O9—H9WB105.2
C16—C17—C22121.5 (2)
N1—C1—C2—C3−0.1 (4)C18—C19—C23—O8177.5 (2)
C1—C2—C3—C40.9 (4)C20—C19—C23—O80.7 (4)
C2—C3—C4—C5−0.2 (4)C18—C19—C23—O7−0.9 (3)
C2—C3—C4—C12178.8 (2)C20—C19—C23—O7−177.7 (2)
C3—C4—C5—N1−1.4 (3)C2—C1—N1—C5−1.4 (4)
C12—C4—C5—N1179.49 (19)C2—C1—N1—Ni1−177.93 (17)
C3—C4—C5—C6176.1 (2)C4—C5—N1—C12.2 (3)
C12—C4—C5—C6−3.1 (3)C6—C5—N1—C1−175.4 (2)
N1—C5—C6—N21.3 (3)C4—C5—N1—Ni1179.18 (17)
C4—C5—C6—N2−176.32 (19)C6—C5—N1—Ni11.6 (2)
N1—C5—C6—C7179.14 (19)O3—Ni1—N1—C1154.2 (5)
C4—C5—C6—C71.6 (3)N2—Ni1—N1—C1174.0 (2)
N2—C6—C7—C80.9 (3)O1—Ni1—N1—C181.8 (2)
C5—C6—C7—C8−176.9 (2)O2—Ni1—N1—C1−8.6 (2)
N2—C6—C7—C11178.9 (2)O4i—Ni1—N1—C1−96.8 (2)
C5—C6—C7—C111.1 (3)O3—Ni1—N1—C5−22.5 (7)
C6—C7—C8—C90.2 (3)N2—Ni1—N1—C5−2.66 (15)
C11—C7—C8—C9−177.6 (2)O1—Ni1—N1—C5−94.83 (16)
C7—C8—C9—C10−0.4 (4)O2—Ni1—N1—C5174.76 (15)
C8—C9—C10—N2−0.5 (4)O4i—Ni1—N1—C586.53 (15)
C8—C7—C11—C12175.6 (2)C9—C10—N2—C61.5 (3)
C6—C7—C11—C12−2.2 (3)C9—C10—N2—Ni1−178.89 (16)
C8—C7—C11—N3−2.5 (4)C7—C6—N2—C10−1.7 (3)
C6—C7—C11—N3179.7 (2)C5—C6—N2—C10176.17 (19)
N3—C11—C12—N40.7 (3)C7—C6—N2—Ni1178.65 (16)
C7—C11—C12—N4−177.7 (2)C5—C6—N2—Ni1−3.5 (2)
N3—C11—C12—C4179.1 (2)O3—Ni1—N2—C101.62 (19)
C7—C11—C12—C40.7 (4)N1—Ni1—N2—C10−176.3 (2)
C3—C4—C12—C11−177.0 (2)O1—Ni1—N2—C10−86.85 (19)
C5—C4—C12—C112.0 (3)O2—Ni1—N2—C10142.9 (9)
C3—C4—C12—N40.9 (4)O4i—Ni1—N2—C1089.23 (19)
C5—C4—C12—N4179.9 (2)O3—Ni1—N2—C6−178.76 (15)
O3—C14—C15—C1634.7 (3)N1—Ni1—N2—C63.35 (15)
O4—C14—C15—C16−146.4 (2)O1—Ni1—N2—C692.77 (15)
O3—C14—C15—C20−147.8 (2)O2—Ni1—N2—C6−37.4 (10)
O4—C14—C15—C2031.1 (3)O4i—Ni1—N2—C6−91.14 (15)
C20—C15—C16—C17−2.2 (3)N4—C13—N3—C11−0.1 (3)
C14—C15—C16—C17175.4 (2)C12—C11—N3—C13−0.4 (3)
C15—C16—C17—C182.0 (3)C7—C11—N3—C13177.8 (2)
C15—C16—C17—C22−175.8 (2)N3—C13—N4—C120.5 (3)
C16—C17—C18—C190.4 (3)C11—C12—N4—C13−0.7 (3)
C22—C17—C18—C19178.3 (2)C4—C12—N4—C13−178.9 (2)
C17—C18—C19—C20−2.6 (3)O4—C14—O3—Ni1−1.4 (3)
C17—C18—C19—C23−179.4 (2)C15—C14—O3—Ni1177.45 (13)
C18—C19—C20—C152.3 (3)N1—Ni1—O3—C14168.8 (6)
C23—C19—C20—C15179.2 (2)N2—Ni1—O3—C14149.23 (18)
C16—C15—C20—C190.0 (3)O1—Ni1—O3—C14−118.78 (18)
C14—C15—C20—C19−177.6 (2)O2—Ni1—O3—C14−28.32 (18)
C18—C17—C22—O5165.0 (2)O4i—Ni1—O3—C1459.44 (18)
C16—C17—C22—O5−17.2 (3)O3—C14—O4—Ni1i−101.9 (2)
C18—C17—C22—O6−16.0 (3)C15—C14—O4—Ni1i79.2 (2)
C16—C17—C22—O6161.7 (2)
D—H···AD—HH···AD···AD—H···A
N4—H4···O6ii0.861.932.772 (3)165
O1—H1WA···O5iii0.881.822.676 (2)165
O1—H1WB···O8iv0.841.942.741 (2)161
O2—H2WA···N3v0.891.942.798 (3)160
O2—H2WB···O40.891.862.630 (2)144
O7—H7O···O9iv0.851.722.558 (2)166
O9—H9WA···O5iii0.861.882.684 (2)153
O9—H9WB···O6vi0.871.992.813 (3)159
Table 1

Hydrogen-bond geometry (, )

DHA DHHA D A DHA
N4H4O6i 0.861.932.772(3)165
O1H1WAO5ii 0.881.822.676(2)165
O1H1WBO8iii 0.841.942.741(2)161
O2H2WAN3iv 0.891.942.798(3)160
O2H2WBO40.891.862.630(2)144
O7H7OO9iii 0.851.722.558(2)166
O9H9WAO5ii 0.861.882.684(2)153
O9H9WBO6v 0.871.992.813(3)159

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

  2 in total

1.  A short history of SHELX.

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

2.  Interplay of coordinative and supramolecular interactions in formation of a series of metal-organic complexes bearing diverse dimensionalities.

Authors:  Jian-Qiang Liu; Ya-Nan Zhang; Yao-Yu Wang; Jun-Cheng Jin; Elmira Kh Lermontova; Qi-Zhen Shi
Journal:  Dalton Trans       Date:  2009-05-27       Impact factor: 4.390
  2 in total

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