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The preformed nickel(II) com­plex of the 14-membered macrocyclic ligand 1,4,8,11-tetra­aza­cyclo­tetra­decane (cyclam, L), when treated with 4,4′-(di­methyl­silanedi­yl)diphthalic acid (H4A) in a DMF/H2O mixture (4:1 v/v) under heating, leads to [Ni(L)]3(HA)2·3DMF (I·DMF). Redissolution of this com­pound in a DMF/H2O/MeOH mixture (4:1:30 v/v/v) with mild acidification under gentle heating results in the formation of a similar com­pound but containing water and methanol mol­ecules of crystallization, [Ni(L)]3(HA)2·5H2O·2MeOH (II·H2O). At lower temperature and concentration of reactants and longer reaction time, single crystals of com­position {[{Ni(L)}3(HA)2]·4CH3OH}n (II·MeOH) were isolated. Single-crystal X-ray diffraction analysis of this com­pound, which, according to PXRD is isostructural with II·H2O but different from I·DMF, revealed its two-dimensional (2D) polymeric structure, i.e. poly[[bis­{μ3-4-[(4-carb­oxy-3-carboxyl­atophen­yl)di­methyl­sil­yl]benzene-1,2-di­carboxyl­ato-κ3O1:O2:O3′}­tris­(1,4,8,11-tetra­aza­cyclo­tetra­decane-κ4N)trinickel(II)] methanol tetra­solvate], {[Ni3(C18H13O8Si)2(C10H24N4)3]·4CH3OH}n. It is built up of the monoprotonated tricarboxyl­ate HA3− ligand coordinated in a monodentate manner in the axial positions of two crystallographically independent NiII cations, one of which is located on a crystallographic inversion centre. Both metal ions adopt a slightly tetra­gonally elongated trans-N4O2 octa­hedral geometry. The com­pound has a lamellar structure with polymeric layers oriented parallel to the (10\overline{2}) plane, which are in turn linked via hydrogen bonds involving protonated carb­oxy­lic acid groups of the ligand. Bulk com­pounds I·DMF and II·H2O were characterized by FT–IR and diffuse reflectance spectroscopy and thermogravimetry, which provide evidence of their structural differences.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620005008/qf3038sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005008/qf3038Isup2.hkl
Contains datablock I

CCDC reference: 1995828

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRP (Agilent, 2014); program(s) used to solve structure: OLEX2 (Dolomanov et al., 2009); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010) and PLATON (Spek, 2020).

Poly[[bis{µ3-4-[(4-carboxy-3-carboxylatophenyl)dimethylsilyl]benzene-1,2-dicarboxylato-κ3O1:O2:O3'}-tris(1,4,8,11-tetraazacyclotetradecane-κ4N)trinickel(II)] methanol tetrasolvate] top
Crystal data top
[Ni3(C18H13O8Si)2(C10H24N4)3]·4CH4OF(000) = 1780
Mr = 1676.04Dx = 1.362 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.5400 (7) ÅCell parameters from 3580 reflections
b = 14.0473 (6) Åθ = 1.9–26.3°
c = 22.0478 (12) ŵ = 0.79 mm1
β = 102.895 (5)°T = 160 K
V = 4087.7 (4) Å3Irregular, light violet
Z = 20.25 × 0.10 × 0.03 mm
Data collection top
Agilent Xcalibur Eos
diffractometer
5410 reflections with I > 2σ(I)
Detector resolution: 8.0797 pixels mm-1Rint = 0.062
ω scansθmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
h = 1616
Tmin = 0.898, Tmax = 1.000k = 1717
20822 measured reflectionsl = 2717
8041 independent reflections
Refinement top
Refinement on F2141 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.068H-atom parameters constrained
wR(F2) = 0.130 w = 1/[σ2(Fo2) + (0.0379P)2 + 4.0667P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
8041 reflectionsΔρmax = 0.64 e Å3
519 parametersΔρmin = 0.41 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Crystallographic measurements were carried out with an Oxford-Diffraction Xcalibur E CCD diffractometer equipped with graphite-monochromated Mo-Ka radiation. The unit cell determination and data integration were carried out using the CrysAlis package of Oxford Diffraction. The structure was solved by direct methods using Olex2 and refined by full-matrix least-squares on F2. Atomic displacements for non-hydrogen atoms were refined using an anisotropic model.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ni10.5000000.5000000.5000000.01529 (18)
Ni20.02509 (4)0.24865 (4)0.14648 (2)0.02124 (15)
Si10.45189 (9)0.02454 (7)0.36702 (5)0.0187 (3)
O10.5459 (2)0.35919 (18)0.48894 (13)0.0223 (7)
O20.7037 (2)0.3513 (2)0.54473 (14)0.0343 (8)
O30.8684 (2)0.19926 (18)0.56857 (12)0.0229 (7)
C310.1371 (3)0.2434 (3)0.26931 (19)0.0231 (10)
C20.5614 (4)0.5186 (3)0.6311 (2)0.0377 (13)
H2A0.5272830.5785120.6341850.045*
H2B0.6106340.5080340.6697740.045*
O40.8792 (2)0.2890 (2)0.48579 (13)0.0274 (7)
N20.6122 (3)0.5221 (2)0.57947 (15)0.0245 (9)
H20.6567650.4664210.5838700.029*
N10.4131 (3)0.4540 (2)0.55990 (16)0.0280 (9)
H10.3684370.5065290.5655980.034*
O50.0727 (2)0.19903 (19)0.22917 (13)0.0299 (8)
C160.6313 (3)0.3196 (3)0.50553 (18)0.0193 (9)
C70.1445 (9)0.2664 (8)0.0903 (8)0.027 (4)0.781 (3)
H7A0.1742830.2585480.0544510.032*0.781 (3)
H7B0.1970200.2557120.1274590.032*0.781 (3)
O10X0.7373 (8)0.4040 (8)0.4033 (5)0.0358 (12)*0.48 (2)
H10X0.7716540.3749720.4328950.054*0.48 (2)
O60.1691 (2)0.3255 (2)0.26436 (14)0.0379 (9)
N30.0532 (3)0.3723 (3)0.14296 (19)0.0255 (6)0.781 (3)
H30.1069030.3739190.1809890.031*0.781 (3)
C300.1874 (3)0.1883 (3)0.32705 (19)0.0201 (10)
C50.3493 (4)0.3713 (3)0.5383 (2)0.0404 (13)
H5A0.3113350.3546490.5691980.049*
H5B0.3919850.3176000.5336100.049*
C120.2009 (5)0.2257 (5)0.1937 (3)0.0397 (18)0.781 (3)
H12A0.2497120.2385670.1551260.048*0.781 (3)
H12B0.2351580.2312520.2277020.048*0.781 (3)
C230.5584 (3)0.1779 (3)0.44063 (17)0.0164 (9)
H230.4948550.2053010.4372560.020*
O80.0036 (3)0.2773 (3)0.34502 (16)0.0547 (11)
C40.2763 (3)0.3906 (3)0.4768 (2)0.0391 (13)
H4A0.2429310.4509760.4798810.047*
H4B0.2245450.3415940.4700730.047*
C30.6773 (3)0.6059 (3)0.5797 (2)0.0353 (12)
H3A0.7310660.6049790.6170340.042*
H3B0.6375410.6631230.5807410.042*
C250.4601 (4)0.0213 (3)0.28406 (19)0.0361 (12)
H25A0.4046280.0152490.2605540.054*
H25B0.5229370.0076250.2807800.054*
H25C0.4569130.0849560.2679610.054*
C280.2047 (3)0.1289 (3)0.43107 (19)0.0233 (10)
H280.1809370.1243940.4674070.028*
C270.2943 (3)0.0831 (3)0.42732 (19)0.0253 (10)
H270.3295880.0487380.4613750.030*
C170.6432 (3)0.2261 (3)0.47454 (18)0.0173 (9)
C330.2767 (3)0.1406 (3)0.32442 (18)0.0199 (9)
H330.3005000.1443550.2880450.024*
C60.1043 (4)0.3649 (4)0.0911 (2)0.0291 (14)0.781 (3)
H6A0.1593660.4105710.0963770.035*0.781 (3)
H6B0.0569200.3785110.0520790.035*0.781 (3)
N40.0623 (3)0.1956 (3)0.0874 (2)0.0255 (6)0.781 (3)
H40.0197630.1998780.0452520.031*0.781 (3)
C290.1505 (3)0.1811 (3)0.38124 (19)0.0199 (9)
O70.0295 (3)0.2155 (3)0.43904 (15)0.0499 (10)
H70.0230850.2439480.4396730.075*
C260.3318 (3)0.0875 (3)0.37398 (18)0.0186 (9)
N60.1174 (3)0.2954 (3)0.20186 (19)0.0255 (6)0.781 (3)
H60.0789420.2895760.2449700.031*0.781 (3)
C320.0538 (3)0.2297 (3)0.3849 (2)0.0240 (10)
O90.3328 (7)0.3757 (7)0.2170 (6)0.0674 (17)*0.68 (4)
H90.2932740.3670230.2397360.101*0.68 (4)
C190.8356 (3)0.2299 (3)0.51494 (19)0.0202 (9)
C240.4528 (3)0.0978 (3)0.3994 (2)0.0373 (12)
H24A0.3988310.1342640.3744090.056*
H24B0.4435880.0944320.4413190.056*
H24C0.5164880.1277490.3993420.056*
C180.7381 (3)0.1856 (3)0.47911 (18)0.0181 (9)
C200.7464 (3)0.0995 (3)0.44918 (19)0.0241 (10)
H200.8101440.0730270.4516800.029*
C220.5645 (3)0.0906 (3)0.41168 (18)0.0184 (9)
C110.1600 (6)0.1274 (5)0.1921 (3)0.0366 (19)0.781 (3)
H11A0.1135280.1129840.2312890.044*0.781 (3)
H11B0.2148520.0814800.1855870.044*0.781 (3)
N50.1068 (3)0.1223 (3)0.1407 (2)0.0255 (6)0.781 (3)
H50.1583620.1239630.1016790.031*0.781 (3)
C10.4855 (4)0.4385 (3)0.6197 (2)0.0374 (12)
H1A0.5202270.3783140.6187420.045*
H1B0.4495870.4360970.6531020.045*
C210.6620 (3)0.0527 (3)0.41600 (19)0.0252 (10)
H210.6696020.0044250.3962460.030*
C140.0612 (7)0.4600 (4)0.1967 (4)0.043 (2)0.781 (3)
H14A0.0117480.4439020.2343700.051*0.781 (3)
H14B0.0840500.5243250.2019510.051*0.781 (3)
C130.1487 (5)0.3959 (4)0.1925 (3)0.0352 (17)0.781 (3)
H13A0.1940520.4030070.1519860.042*0.781 (3)
H13B0.1855790.4140380.2237660.042*0.781 (3)
C90.0076 (5)0.0287 (4)0.0886 (3)0.0377 (17)0.781 (3)
H9A0.0397550.0426950.0496300.045*0.781 (3)
H9B0.0313930.0360330.0859990.045*0.781 (3)
C100.0483 (6)0.0339 (4)0.1407 (3)0.0317 (16)0.781 (3)
H10A0.0941280.0199160.1373490.038*0.781 (3)
H10B0.0003450.0285870.1802080.038*0.781 (3)
C80.0974 (4)0.0958 (4)0.0954 (3)0.0321 (15)0.781 (3)
H8A0.1415640.0878500.1362900.039*0.781 (3)
H8B0.1358530.0804620.0645060.039*0.781 (3)
C340.3987 (13)0.2921 (7)0.2204 (10)0.065 (3)*0.68 (4)
H34A0.3598120.2388970.2007610.097*0.68 (4)
H34B0.4272400.2770480.2632520.097*0.68 (4)
H34C0.4522560.3055120.1995790.097*0.68 (4)
C35X0.7232 (12)0.3482 (13)0.3502 (5)0.051 (2)*0.48 (2)
H35A0.6779700.3799380.3165490.076*0.48 (2)
H35B0.6946750.2880050.3578880.076*0.48 (2)
H35C0.7872220.3379070.3393380.076*0.48 (2)
N4X0.0201 (11)0.1303 (7)0.1066 (6)0.0255 (6)0.219 (3)
H4X0.0190830.1281370.0635190.031*0.219 (3)
N3X0.0984 (8)0.3195 (9)0.1288 (7)0.0255 (6)0.219 (3)
H3X0.1493150.3194450.1681300.031*0.219 (3)
N6X0.0630 (11)0.3656 (7)0.1946 (6)0.0255 (6)0.219 (3)
H6X0.0202040.3616200.2367110.031*0.219 (3)
N5X0.1493 (9)0.1931 (12)0.1737 (7)0.0255 (6)0.219 (3)
H5X0.2037880.1948570.1360680.031*0.219 (3)
C15X0.0851 (19)0.4200 (11)0.1095 (10)0.035 (6)*0.219 (3)
H15A0.0308870.4230840.0724690.042*0.219 (3)
H15B0.1465990.4407050.0978640.042*0.219 (3)
C8X0.004 (2)0.0390 (15)0.1358 (14)0.046 (7)*0.219 (3)
H8XA0.0542470.0315770.1743650.056*0.219 (3)
H8XB0.0121440.0128580.1083250.056*0.219 (3)
C14X0.062 (2)0.4892 (19)0.1551 (13)0.057 (8)*0.219 (3)
H14C0.0578030.5530080.1378970.068*0.219 (3)
H14D0.1150330.4882450.1928210.068*0.219 (3)
C13X0.044 (3)0.4604 (14)0.1705 (15)0.039 (9)*0.219 (3)
H13C0.0568430.5066640.2003820.046*0.219 (3)
H13D0.0948940.4700890.1326270.046*0.219 (3)
C9X0.1043 (19)0.0343 (18)0.1495 (12)0.039 (7)*0.219 (3)
H9XA0.1511090.0434180.1096220.047*0.219 (3)
H9XB0.1130880.0310440.1615110.047*0.219 (3)
C12X0.1684 (13)0.3533 (18)0.2014 (13)0.036 (7)*0.219 (3)
H12C0.1814660.3956710.2334450.043*0.219 (3)
H12D0.2151850.3690640.1625730.043*0.219 (3)
C11X0.183 (2)0.2582 (18)0.2176 (12)0.039 (8)*0.219 (3)
H11C0.2542100.2474240.2163800.047*0.219 (3)
H11D0.1448730.2458210.2595410.047*0.219 (3)
C10X0.142 (3)0.0920 (13)0.1927 (17)0.046 (7)*0.219 (3)
H10C0.0974330.0863400.2335840.056*0.219 (3)
H10D0.2085810.0693450.1955220.056*0.219 (3)
C7X0.1229 (14)0.162 (2)0.1048 (14)0.060 (8)*0.219 (3)
H7XA0.1656300.1520890.1459570.072*0.219 (3)
H7XB0.1479550.1197030.0766680.072*0.219 (3)
C150.0057 (6)0.4615 (4)0.1426 (3)0.0365 (18)0.781 (3)
H15C0.0546440.4675590.1033070.044*0.781 (3)
H15D0.0395850.5158580.1470690.044*0.781 (3)
C6X0.136 (4)0.253 (3)0.087 (3)0.036 (15)*0.219 (3)
H6XA0.1001850.2631710.0446840.043*0.219 (3)
H6XB0.2078420.2649450.0898990.043*0.219 (3)
C34X0.423 (2)0.3000 (19)0.2420 (18)0.065 (3)*0.32 (4)
H34D0.4202720.2373300.2242670.097*0.32 (4)
H34E0.4132270.2956890.2837620.097*0.32 (4)
H34F0.4873600.3283460.2424110.097*0.32 (4)
O9X0.3422 (17)0.3587 (19)0.2046 (11)0.0674 (17)*0.32 (4)
H9X0.2998930.3661540.2267720.101*0.32 (4)
O100.7548 (8)0.4224 (7)0.4134 (4)0.0358 (12)*0.52 (2)
H100.7944500.3904130.4389300.054*0.52 (2)
C350.7467 (11)0.3841 (13)0.3541 (5)0.051 (2)*0.52 (2)
H35D0.7387710.4347260.3241180.076*0.52 (2)
H35E0.6889180.3427530.3443270.076*0.52 (2)
H35F0.8068770.3486270.3530560.076*0.52 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0109 (4)0.0181 (4)0.0156 (4)0.0010 (3)0.0003 (3)0.0051 (3)
Ni20.0139 (3)0.0239 (3)0.0236 (3)0.0023 (3)0.0008 (2)0.0066 (2)
Si10.0174 (6)0.0192 (6)0.0165 (6)0.0000 (5)0.0024 (5)0.0034 (5)
O10.0123 (14)0.0202 (14)0.0316 (17)0.0048 (13)0.0012 (13)0.0091 (13)
O20.0201 (17)0.0324 (17)0.043 (2)0.0071 (15)0.0089 (15)0.0219 (15)
O30.0206 (16)0.0264 (15)0.0186 (16)0.0065 (14)0.0027 (13)0.0037 (13)
C310.020 (2)0.024 (2)0.023 (2)0.005 (2)0.0006 (19)0.0066 (19)
C20.033 (3)0.054 (3)0.022 (3)0.014 (3)0.002 (2)0.010 (2)
O40.0184 (16)0.0333 (17)0.0291 (18)0.0000 (14)0.0026 (14)0.0016 (14)
N20.0192 (19)0.0255 (19)0.025 (2)0.0058 (17)0.0034 (16)0.0097 (16)
N10.023 (2)0.031 (2)0.031 (2)0.0024 (18)0.0099 (18)0.0001 (17)
O50.0236 (17)0.0259 (16)0.0308 (18)0.0038 (14)0.0136 (15)0.0085 (14)
C160.016 (2)0.021 (2)0.020 (2)0.0002 (19)0.0025 (19)0.0035 (18)
C70.022 (5)0.038 (6)0.022 (5)0.004 (4)0.008 (3)0.003 (3)
O60.045 (2)0.0265 (17)0.0320 (19)0.0087 (16)0.0140 (16)0.0089 (14)
N30.0211 (13)0.0298 (13)0.0212 (12)0.0014 (11)0.0047 (10)0.0019 (10)
C300.021 (2)0.0124 (19)0.023 (2)0.0031 (19)0.0036 (19)0.0010 (17)
C50.029 (3)0.038 (3)0.057 (4)0.006 (2)0.014 (3)0.002 (3)
C120.031 (4)0.055 (5)0.033 (4)0.006 (4)0.008 (3)0.003 (4)
C230.012 (2)0.018 (2)0.018 (2)0.0049 (18)0.0027 (17)0.0007 (16)
O80.044 (2)0.077 (3)0.046 (2)0.038 (2)0.0169 (19)0.026 (2)
C40.019 (3)0.031 (3)0.064 (4)0.011 (2)0.003 (3)0.008 (2)
C30.023 (3)0.031 (3)0.045 (3)0.002 (2)0.008 (2)0.018 (2)
C250.032 (3)0.049 (3)0.025 (3)0.009 (2)0.000 (2)0.009 (2)
C280.022 (2)0.031 (2)0.017 (2)0.002 (2)0.0033 (19)0.0016 (19)
C270.022 (2)0.030 (2)0.021 (2)0.000 (2)0.002 (2)0.0021 (19)
C170.016 (2)0.015 (2)0.020 (2)0.0013 (18)0.0029 (18)0.0010 (16)
C330.019 (2)0.024 (2)0.014 (2)0.005 (2)0.0006 (18)0.0003 (18)
C60.025 (3)0.025 (3)0.035 (4)0.004 (3)0.004 (3)0.012 (3)
N40.0211 (13)0.0298 (13)0.0212 (12)0.0014 (11)0.0047 (10)0.0019 (10)
C290.015 (2)0.021 (2)0.021 (2)0.0027 (19)0.0024 (18)0.0035 (17)
O70.033 (2)0.081 (3)0.039 (2)0.030 (2)0.0160 (18)0.0093 (19)
C260.015 (2)0.017 (2)0.020 (2)0.0014 (18)0.0047 (18)0.0013 (17)
N60.0211 (13)0.0298 (13)0.0212 (12)0.0014 (11)0.0047 (10)0.0019 (10)
C320.022 (2)0.026 (2)0.022 (2)0.001 (2)0.001 (2)0.0058 (19)
C190.015 (2)0.020 (2)0.024 (2)0.0072 (19)0.0020 (19)0.0036 (18)
C240.030 (3)0.029 (2)0.049 (3)0.003 (2)0.001 (3)0.001 (2)
C180.017 (2)0.020 (2)0.016 (2)0.0023 (19)0.0005 (18)0.0021 (17)
C200.015 (2)0.023 (2)0.032 (3)0.007 (2)0.001 (2)0.0060 (19)
C220.016 (2)0.021 (2)0.015 (2)0.0035 (19)0.0025 (18)0.0007 (17)
C110.030 (4)0.043 (5)0.033 (4)0.016 (4)0.002 (3)0.008 (4)
N50.0211 (13)0.0298 (13)0.0212 (12)0.0014 (11)0.0047 (10)0.0019 (10)
C10.041 (3)0.054 (3)0.021 (3)0.002 (3)0.015 (2)0.008 (2)
C210.023 (2)0.020 (2)0.030 (3)0.003 (2)0.001 (2)0.0134 (19)
C140.064 (6)0.032 (4)0.029 (4)0.026 (4)0.005 (4)0.010 (3)
C130.041 (4)0.033 (4)0.033 (4)0.019 (4)0.011 (3)0.000 (3)
C90.036 (4)0.020 (3)0.053 (5)0.002 (3)0.001 (3)0.005 (3)
C100.033 (4)0.025 (3)0.036 (4)0.002 (3)0.004 (3)0.007 (3)
C80.024 (3)0.032 (3)0.040 (4)0.014 (3)0.007 (3)0.006 (3)
N4X0.0211 (13)0.0298 (13)0.0212 (12)0.0014 (11)0.0047 (10)0.0019 (10)
N3X0.0211 (13)0.0298 (13)0.0212 (12)0.0014 (11)0.0047 (10)0.0019 (10)
N6X0.0211 (13)0.0298 (13)0.0212 (12)0.0014 (11)0.0047 (10)0.0019 (10)
N5X0.0211 (13)0.0298 (13)0.0212 (12)0.0014 (11)0.0047 (10)0.0019 (10)
C150.050 (5)0.014 (3)0.037 (4)0.003 (3)0.006 (4)0.016 (3)
Geometric parameters (Å, º) top
Ni1—N1i2.059 (4)C19—C181.513 (5)
Ni1—N12.059 (4)C24—H24A0.9600
Ni1—N2i2.070 (3)C24—H24B0.9600
Ni1—N22.070 (3)C24—H24C0.9600
Ni1—O1i2.104 (2)C18—C201.395 (5)
Ni1—O12.104 (2)C20—C211.378 (5)
Ni2—N4X2.037 (7)C20—H200.9300
Ni2—N62.041 (4)C22—C211.407 (5)
Ni2—N32.045 (4)C11—N51.474 (6)
Ni2—N3X2.057 (7)C11—H11A0.9700
Ni2—N5X2.060 (8)C11—H11B0.9700
Ni2—N52.080 (4)N5—C101.472 (5)
Ni2—N6X2.081 (7)N5—H50.9800
Ni2—N42.083 (4)C1—H1A0.9700
Ni2—O3ii2.112 (3)C1—H1B0.9700
Ni2—O52.118 (3)C21—H210.9300
Si1—C251.858 (4)C14—C131.475 (10)
Si1—C241.860 (4)C14—C151.545 (10)
Si1—C221.867 (4)C14—H14A0.9700
Si1—C261.887 (4)C14—H14B0.9700
O1—C161.262 (4)C13—H13A0.9700
O2—C161.236 (4)C13—H13B0.9700
O3—C191.243 (4)C9—C101.514 (9)
C31—O61.246 (5)C9—C81.519 (8)
C31—O51.260 (5)C9—H9A0.9700
C31—C301.515 (5)C9—H9B0.9700
C2—N21.455 (5)C10—H10A0.9700
C2—C11.507 (6)C10—H10B0.9700
C2—H2A0.9700C8—H8A0.9700
C2—H2B0.9700C8—H8B0.9700
O4—C191.273 (5)C34—H34A0.9600
N2—C31.470 (5)C34—H34B0.9600
N2—H20.9800C34—H34C0.9600
N1—C51.462 (5)C35X—H35A0.9600
N1—C11.472 (5)C35X—H35B0.9600
N1—H10.9800C35X—H35C0.9600
C16—C171.506 (5)N4X—C7X1.469 (8)
C7—N41.483 (8)N4X—C8X1.473 (8)
C7—C61.489 (14)N4X—H4X0.9800
C7—H7A0.9700N3X—C15X1.473 (8)
C7—H7B0.9700N3X—C6X1.476 (8)
O10X—C35X1.387 (8)N3X—H3X0.9800
O10X—H10X0.8199N6X—C13X1.478 (8)
N3—C61.467 (5)N6X—C12X1.479 (8)
N3—C151.485 (5)N6X—H6X0.9800
N3—H30.9800N5X—C11X1.48 (3)
C30—C331.395 (5)N5X—C10X1.477 (8)
C30—C291.398 (6)N5X—H5X0.9800
C5—C41.513 (6)C15X—C14X1.48 (3)
C5—H5A0.9700C15X—H15A0.9700
C5—H5B0.9700C15X—H15B0.9700
C12—N61.476 (6)C8X—C9X1.56 (3)
C12—C111.490 (9)C8X—H8XA0.9700
C12—H12A0.9700C8X—H8XB0.9700
C12—H12B0.9700C14X—C13X1.59 (4)
C23—C221.393 (5)C14X—H14C0.9700
C23—C171.398 (5)C14X—H14D0.9700
C23—H230.9300C13X—H13C0.9700
O8—C321.190 (5)C13X—H13D0.9700
C4—C3i1.516 (7)C9X—C10X1.43 (4)
C4—H4A0.9700C9X—H9XA0.9700
C4—H4B0.9700C9X—H9XB0.9700
C3—H3A0.9700C12X—C11X1.41 (3)
C3—H3B0.9700C12X—H12C0.9700
C25—H25A0.9600C12X—H12D0.9700
C25—H25B0.9600C11X—H11C0.9700
C25—H25C0.9600C11X—H11D0.9700
C28—C291.388 (5)C10X—H10C0.9700
C28—C271.391 (6)C10X—H10D0.9700
C28—H280.9300C7X—C6X1.37 (6)
C27—C261.383 (6)C7X—H7XA0.9700
C27—H270.9300C7X—H7XB0.9700
C17—C181.388 (5)C15—H15C0.9700
C33—C261.394 (5)C15—H15D0.9700
C33—H330.9300C6X—H6XA0.9700
C6—H6A0.9700C6X—H6XB0.9700
C6—H6B0.9700C34X—O9X1.466 (10)
N4—C81.479 (5)C34X—H34D0.9600
N4—H40.9800C34X—H34E0.9600
C29—C321.494 (6)C34X—H34F0.9600
O7—C321.321 (5)O9X—H9X0.8394
O7—H70.8200O10—C351.396 (8)
N6—C131.475 (5)O10—H100.8200
N6—H60.9800C35—H35D0.9600
O9—C341.467 (8)C35—H35E0.9600
O9—H90.8199C35—H35F0.9600
N1i—Ni1—N1180.0C20—C18—C19116.8 (3)
N1i—Ni1—N2i85.45 (14)C21—C20—C18121.3 (4)
N1—Ni1—N2i94.56 (14)C21—C20—H20119.3
N1i—Ni1—N294.56 (14)C18—C20—H20119.3
N1—Ni1—N285.44 (14)C23—C22—C21116.9 (4)
N2i—Ni1—N2180.0 (2)C23—C22—Si1123.7 (3)
N1i—Ni1—O1i90.28 (13)C21—C22—Si1119.4 (3)
N1—Ni1—O1i89.72 (13)N5—C11—C12108.1 (5)
N2i—Ni1—O1i93.42 (11)N5—C11—H11A110.1
N2—Ni1—O1i86.58 (11)C12—C11—H11A110.1
N1i—Ni1—O189.72 (13)N5—C11—H11B110.1
N1—Ni1—O190.28 (13)C12—C11—H11B110.1
N2i—Ni1—O186.58 (11)H11A—C11—H11B108.4
N2—Ni1—O193.42 (11)C10—N5—C11113.3 (5)
O1i—Ni1—O1180.0C10—N5—Ni2116.2 (4)
N6—Ni2—N398.11 (17)C11—N5—Ni2104.8 (3)
N4X—Ni2—N3X88.7 (6)C10—N5—H5107.4
N4X—Ni2—N5X99.2 (6)C11—N5—H5107.4
N3X—Ni2—N5X171.6 (7)Ni2—N5—H5107.4
N6—Ni2—N585.61 (17)N1—C1—C2109.4 (4)
N3—Ni2—N5174.42 (17)N1—C1—H1A109.8
N4X—Ni2—N6X174.9 (6)C2—C1—H1A109.8
N3X—Ni2—N6X91.0 (6)N1—C1—H1B109.8
N5X—Ni2—N6X80.8 (6)C2—C1—H1B109.8
N6—Ni2—N4176.65 (17)H1A—C1—H1B108.2
N3—Ni2—N484.73 (17)C20—C21—C22120.7 (4)
N5—Ni2—N491.43 (17)C20—C21—H21119.7
N6—Ni2—O3ii88.66 (14)C22—C21—H21119.7
N3—Ni2—O3ii86.59 (14)C13—C14—C15118.9 (6)
N5—Ni2—O3ii89.34 (14)C13—C14—H14A107.6
N4—Ni2—O3ii89.74 (14)C15—C14—H14A107.6
N4X—Ni2—O585.0 (4)C13—C14—H14B107.6
N6—Ni2—O586.54 (15)C15—C14—H14B107.6
N3—Ni2—O594.73 (14)H14A—C14—H14B107.0
N3X—Ni2—O586.8 (4)C14—C13—N6111.9 (5)
N5X—Ni2—O591.1 (4)C14—C13—H13A109.2
N5—Ni2—O589.64 (14)N6—C13—H13A109.2
N6X—Ni2—O589.9 (4)C14—C13—H13B109.2
N4—Ni2—O595.01 (15)N6—C13—H13B109.2
O3ii—Ni2—O5175.16 (12)H13A—C13—H13B107.9
C25—Si1—C24111.0 (2)C10—C9—C8114.8 (6)
C25—Si1—C22108.1 (2)C10—C9—H9A108.6
C24—Si1—C22108.79 (19)C8—C9—H9A108.6
C25—Si1—C26109.48 (19)C10—C9—H9B108.6
C24—Si1—C26109.5 (2)C8—C9—H9B108.6
C22—Si1—C26109.92 (17)H9A—C9—H9B107.6
C16—O1—Ni1131.0 (2)N5—C10—C9113.6 (5)
C19—O3—Ni2iii133.4 (3)N5—C10—H10A108.8
O6—C31—O5126.6 (4)C9—C10—H10A108.8
O6—C31—C30116.5 (4)N5—C10—H10B108.8
O5—C31—C30116.7 (4)C9—C10—H10B108.8
N2—C2—C1108.6 (4)H10A—C10—H10B107.7
N2—C2—H2A110.0N4—C8—C9110.4 (4)
C1—C2—H2A110.0N4—C8—H8A109.6
N2—C2—H2B110.0C9—C8—H8A109.6
C1—C2—H2B110.0N4—C8—H8B109.6
H2A—C2—H2B108.4C9—C8—H8B109.6
C2—N2—C3114.3 (4)H8A—C8—H8B108.1
C2—N2—Ni1105.7 (3)O9—C34—H34A109.5
C3—N2—Ni1116.7 (3)O9—C34—H34B109.5
C2—N2—H2106.5H34A—C34—H34B109.5
C3—N2—H2106.5O9—C34—H34C109.5
Ni1—N2—H2106.5H34A—C34—H34C109.5
C5—N1—C1113.7 (3)H34B—C34—H34C109.5
C5—N1—Ni1114.9 (3)O10X—C35X—H35A109.5
C1—N1—Ni1105.0 (3)O10X—C35X—H35B109.5
C5—N1—H1107.6H35A—C35X—H35B109.5
C1—N1—H1107.6O10X—C35X—H35C109.5
Ni1—N1—H1107.6H35A—C35X—H35C109.5
C31—O5—Ni2130.1 (3)H35B—C35X—H35C109.5
O2—C16—O1125.2 (4)C7X—N4X—C8X120.5 (19)
O2—C16—C17118.9 (3)C7X—N4X—Ni298.4 (13)
O1—C16—C17115.9 (3)C8X—N4X—Ni2115.7 (15)
N4—C7—C6110.6 (8)C7X—N4X—H4X107.1
N4—C7—H7A109.5C8X—N4X—H4X107.1
C6—C7—H7A109.5Ni2—N4X—H4X107.1
N4—C7—H7B109.5C15X—N3X—C6X118 (3)
C6—C7—H7B109.5C15X—N3X—Ni2117.8 (12)
H7A—C7—H7B108.1C6X—N3X—Ni2102.9 (18)
C35X—O10X—H10X109.7C15X—N3X—H3X105.8
C6—N3—C15113.7 (5)C6X—N3X—H3X105.8
C6—N3—Ni2108.0 (3)Ni2—N3X—H3X105.8
C15—N3—Ni2115.8 (4)C13X—N6X—C12X113.3 (19)
C6—N3—H3106.2C13X—N6X—Ni2116.4 (15)
C15—N3—H3106.2C12X—N6X—Ni2108.2 (12)
Ni2—N3—H3106.2C13X—N6X—H6X106.1
C33—C30—C29118.6 (4)C12X—N6X—H6X106.1
C33—C30—C31116.2 (4)Ni2—N6X—H6X106.1
C29—C30—C31125.1 (4)C11X—N5X—C10X114.8 (19)
N1—C5—C4111.7 (4)C11X—N5X—Ni2110.4 (13)
N1—C5—H5A109.3C10X—N5X—Ni2116.1 (19)
C4—C5—H5A109.3C11X—N5X—H5X104.7
N1—C5—H5B109.3C10X—N5X—H5X104.7
C4—C5—H5B109.3Ni2—N5X—H5X104.7
H5A—C5—H5B107.9N3X—C15X—C14X118 (2)
N6—C12—C11109.8 (5)N3X—C15X—H15A107.9
N6—C12—H12A109.7C14X—C15X—H15A107.9
C11—C12—H12A109.7N3X—C15X—H15B107.9
N6—C12—H12B109.7C14X—C15X—H15B107.9
C11—C12—H12B109.7H15A—C15X—H15B107.2
H12A—C12—H12B108.2N4X—C8X—C9X111 (2)
C22—C23—C17123.1 (4)N4X—C8X—H8XA109.4
C22—C23—H23118.5C9X—C8X—H8XA109.4
C17—C23—H23118.5N4X—C8X—H8XB109.4
C5—C4—C3i115.7 (4)C9X—C8X—H8XB109.4
C5—C4—H4A108.4H8XA—C8X—H8XB108.0
C3i—C4—H4A108.4C15X—C14X—C13X108 (2)
C5—C4—H4B108.4C15X—C14X—H14C110.0
C3i—C4—H4B108.4C13X—C14X—H14C110.0
H4A—C4—H4B107.4C15X—C14X—H14D110.0
N2—C3—C4i112.4 (4)C13X—C14X—H14D110.0
N2—C3—H3A109.1H14C—C14X—H14D108.4
C4i—C3—H3A109.1N6X—C13X—C14X123 (2)
N2—C3—H3B109.1N6X—C13X—H13C106.6
C4i—C3—H3B109.1C14X—C13X—H13C106.6
H3A—C3—H3B107.9N6X—C13X—H13D106.6
Si1—C25—H25A109.5C14X—C13X—H13D106.6
Si1—C25—H25B109.5H13C—C13X—H13D106.5
H25A—C25—H25B109.5C10X—C9X—C8X126 (3)
Si1—C25—H25C109.5C10X—C9X—H9XA105.7
H25A—C25—H25C109.5C8X—C9X—H9XA105.7
H25B—C25—H25C109.5C10X—C9X—H9XB105.7
C29—C28—C27120.8 (4)C8X—C9X—H9XB105.7
C29—C28—H28119.6H9XA—C9X—H9XB106.1
C27—C28—H28119.6C11X—C12X—N6X109 (2)
C26—C27—C28121.3 (4)C11X—C12X—H12C109.8
C26—C27—H27119.3N6X—C12X—H12C109.8
C28—C27—H27119.3C11X—C12X—H12D109.8
C18—C17—C23118.5 (3)N6X—C12X—H12D109.8
C18—C17—C16121.0 (3)H12C—C12X—H12D108.3
C23—C17—C16120.5 (3)C12X—C11X—N5X110 (2)
C26—C33—C30122.8 (4)C12X—C11X—H11C109.7
C26—C33—H33118.6N5X—C11X—H11C109.7
C30—C33—H33118.6C12X—C11X—H11D109.7
N3—C6—C7108.1 (6)N5X—C11X—H11D109.7
N3—C6—H6A110.1H11C—C11X—H11D108.2
C7—C6—H6A110.1C9X—C10X—N5X111 (3)
N3—C6—H6B110.1C9X—C10X—H10C109.3
C7—C6—H6B110.1N5X—C10X—H10C109.3
H6A—C6—H6B108.4C9X—C10X—H10D109.3
C8—N4—C7114.3 (7)N5X—C10X—H10D109.3
C8—N4—Ni2118.5 (3)H10C—C10X—H10D108.0
C7—N4—Ni2105.1 (3)C6X—C7X—N4X118 (3)
C8—N4—H4106.0C6X—C7X—H7XA107.7
C7—N4—H4106.0N4X—C7X—H7XA107.7
Ni2—N4—H4106.0C6X—C7X—H7XB107.7
C28—C29—C30119.2 (4)N4X—C7X—H7XB107.7
C28—C29—C32120.9 (4)H7XA—C7X—H7XB107.1
C30—C29—C32119.9 (4)N3—C15—C14109.7 (5)
C32—O7—H7109.5N3—C15—H15C109.7
C27—C26—C33117.2 (4)C14—C15—H15C109.7
C27—C26—Si1122.3 (3)N3—C15—H15D109.7
C33—C26—Si1120.5 (3)C14—C15—H15D109.7
C13—N6—C12115.4 (5)H15C—C15—H15D108.2
C13—N6—Ni2114.9 (4)C7X—C6X—N3X109 (4)
C12—N6—Ni2105.5 (4)C7X—C6X—H6XA109.8
C13—N6—H6106.8N3X—C6X—H6XA109.8
C12—N6—H6106.8C7X—C6X—H6XB109.8
Ni2—N6—H6106.8N3X—C6X—H6XB109.8
O8—C32—O7122.5 (4)H6XA—C6X—H6XB108.2
O8—C32—C29125.4 (4)O9X—C34X—H34D109.5
O7—C32—C29112.2 (4)O9X—C34X—H34E109.5
C34—O9—H9108.8H34D—C34X—H34E109.5
O3—C19—O4126.8 (4)O9X—C34X—H34F109.5
O3—C19—C18116.0 (4)H34D—C34X—H34F109.5
O4—C19—C18117.0 (4)H34E—C34X—H34F109.5
Si1—C24—H24A109.5C34X—O9X—H9X105.1
Si1—C24—H24B109.5C35—O10—H10109.5
H24A—C24—H24B109.5O10—C35—H35D109.5
Si1—C24—H24C109.5O10—C35—H35E109.5
H24A—C24—H24C109.5H35D—C35—H35E109.5
H24B—C24—H24C109.5O10—C35—H35F109.5
C17—C18—C20119.5 (4)H35D—C35—H35F109.5
C17—C18—C19123.7 (3)H35E—C35—H35F109.5
C1—C2—N2—C3171.2 (4)O3—C19—C18—C1797.3 (5)
C1—C2—N2—Ni141.4 (4)O4—C19—C18—C1787.7 (5)
O6—C31—O5—Ni211.9 (7)O3—C19—C18—C2083.0 (5)
C30—C31—O5—Ni2173.8 (3)O4—C19—C18—C2091.9 (4)
Ni1—O1—C16—O217.1 (7)C17—C18—C20—C211.2 (6)
Ni1—O1—C16—C17163.4 (3)C19—C18—C20—C21179.2 (4)
O6—C31—C30—C3384.5 (5)C17—C23—C22—C212.1 (6)
O5—C31—C30—C3390.4 (5)C17—C23—C22—Si1179.2 (3)
O6—C31—C30—C2996.5 (5)C25—Si1—C22—C23114.2 (4)
O5—C31—C30—C2988.6 (5)C24—Si1—C22—C23125.2 (4)
C1—N1—C5—C4180.0 (4)C26—Si1—C22—C235.3 (4)
Ni1—N1—C5—C459.0 (4)C25—Si1—C22—C2164.5 (4)
N1—C5—C4—C3i73.3 (5)C24—Si1—C22—C2156.2 (4)
C2—N2—C3—C4i176.7 (4)C26—Si1—C22—C21176.1 (3)
Ni1—N2—C3—C4i52.6 (4)N6—C12—C11—N558.2 (7)
C29—C28—C27—C260.4 (6)C12—C11—N5—C10170.3 (5)
C22—C23—C17—C180.6 (6)C12—C11—N5—Ni242.6 (6)
C22—C23—C17—C16179.1 (4)C5—N1—C1—C2168.1 (4)
O2—C16—C17—C1813.7 (6)Ni1—N1—C1—C241.8 (4)
O1—C16—C17—C18166.8 (4)N2—C2—C1—N158.0 (5)
O2—C16—C17—C23166.0 (4)C18—C20—C21—C220.4 (7)
O1—C16—C17—C2313.5 (6)C23—C22—C21—C201.9 (6)
C29—C30—C33—C261.3 (6)Si1—C22—C21—C20179.3 (3)
C31—C30—C33—C26179.6 (4)C15—C14—C13—N673.3 (7)
C15—N3—C6—C7170.0 (7)C12—N6—C13—C14175.5 (6)
Ni2—N3—C6—C740.1 (7)Ni2—N6—C13—C1452.4 (6)
N4—C7—C6—N355.0 (12)C11—N5—C10—C9179.3 (6)
C6—C7—N4—C8171.7 (8)Ni2—N5—C10—C957.8 (6)
C6—C7—N4—Ni240.2 (12)C8—C9—C10—N570.8 (7)
C27—C28—C29—C300.7 (6)C7—N4—C8—C9177.1 (8)
C27—C28—C29—C32179.5 (4)Ni2—N4—C8—C958.1 (6)
C33—C30—C29—C281.5 (6)C10—C9—C8—N469.2 (7)
C31—C30—C29—C28179.5 (4)C6X—N3X—C15X—C14X171 (3)
C33—C30—C29—C32178.7 (3)Ni2—N3X—C15X—C14X65 (2)
C31—C30—C29—C320.3 (6)C7X—N4X—C8X—C9X164 (2)
C28—C27—C26—C330.6 (6)Ni2—N4X—C8X—C9X46 (3)
C28—C27—C26—Si1179.0 (3)N3X—C15X—C14X—C13X62 (3)
C30—C33—C26—C270.2 (6)C12X—N6X—C13X—C14X176 (3)
C30—C33—C26—Si1179.8 (3)Ni2—N6X—C13X—C14X50 (3)
C25—Si1—C26—C27165.7 (3)C15X—C14X—C13X—N6X57 (3)
C24—Si1—C26—C2743.8 (4)N4X—C8X—C9X—C10X66 (4)
C22—Si1—C26—C2775.7 (4)C13X—N6X—C12X—C11X173 (2)
C25—Si1—C26—C3313.9 (4)Ni2—N6X—C12X—C11X43 (2)
C24—Si1—C26—C33135.8 (3)N6X—C12X—C11X—N5X51 (3)
C22—Si1—C26—C33104.7 (3)C10X—N5X—C11X—C12X169 (2)
C11—C12—N6—C13169.1 (5)Ni2—N5X—C11X—C12X35 (2)
C11—C12—N6—Ni241.1 (6)C8X—C9X—C10X—N5X66 (4)
C28—C29—C32—O8178.5 (4)C11X—N5X—C10X—C9X177 (2)
C30—C29—C32—O81.3 (6)Ni2—N5X—C10X—C9X46 (3)
C28—C29—C32—O70.4 (5)C8X—N4X—C7X—C6X169 (3)
C30—C29—C32—O7179.7 (4)Ni2—N4X—C7X—C6X42 (3)
Ni2iii—O3—C19—O422.7 (6)C6—N3—C15—C14176.9 (5)
Ni2iii—O3—C19—C18162.8 (2)Ni2—N3—C15—C1451.0 (6)
C23—C17—C18—C201.1 (6)C13—C14—C15—N372.0 (7)
C16—C17—C18—C20179.2 (4)N4X—C7X—C6X—N3X57 (6)
C23—C17—C18—C19179.3 (4)C15X—N3X—C6X—C7X167 (3)
C16—C17—C18—C190.4 (6)Ni2—N3X—C6X—C7X35 (5)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x1, y+1/2, z1/2; (iii) x+1, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O20.982.002.882 (4)148
N3—H3···O60.981.962.861 (5)151
N4—H4···O4ii0.982.062.955 (5)151
N5—H5···O2ii0.982.032.962 (5)157
N6—H6···O80.982.253.225 (5)178
O7—H7···O4iv0.821.952.684 (5)150
N4—H4···O7v0.982.663.437 (6)137
N1—H1···O10i0.982.083.021 (9)160
O9—H9···O60.821.972.745 (11)158
O10—H10···O40.821.972.775 (9)166
Symmetry codes: (i) x+1, y+1, z+1; (ii) x1, y+1/2, z1/2; (iv) x1, y, z; (v) x, y+1/2, z1/2.
Selected bond lengths and angles (Å, °) top
DistancesBite angles
Ni1—N12.059 (4)N1—Ni1—N285.44 (14)
Ni1—N22.070 (3)N1—Ni1—N2i94.55 (14)
Ni1—O12.104 (2)
Ni2—N32.045 (4)N3—Ni2—N484.73 (17)
Ni2—N42.083 (4)N5—Ni2—N685.61 (17)
Ni2—N52.041 (4)N4—Ni2—N591.43 (17)
Ni2—N62.080 (4)N3—Ni2—N698.11 (17)
Ni2—O3ii2.112 (3)
Ni2—O52.118 (3)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, -y+1/2, z-1/2.
 

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