Download citation
Download citation
link to html
The title dicadmium compound, [Cd2(C10H8N2)5(H2O)6](C7H6NO2)2(ClO4)2·2H2O, is located around an inversion centre. Each CdII centre is coordinated by three N atoms from three different 4,4′-bipyridine ligands and three O atoms from three coordinating water mol­ecules in a distorted octa­hedral coordination environment. In the dicadmium cation unit, one 4,4′-bipyridine (4,4′-bipy) molecule acts as a bidentate bridging ligand between two Cd metal ions, while the other four 4,4′-bipy molecules act only as monodentate terminal ligands, resulting in a rare `H-type' [Cd2(C10H8N2)5(H2O)6] host unit. These host units are connected to each other via π–π stacking inter­actions, giving rise to a three-dimensional supra­molecular grid network with large cavities. The 3-am­ino­benzoate anions, perchlorate anions and water mol­ecules are encapsulated in the cavities by numerous hydrogen-bonding inter­actions. To the best of our knowledge, this is the first example of a coordination compound based on both 4,4′-bipyridine ligands together with discrete 3-amino­benzoate anions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270111017690/dn3162sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270111017690/dn3162Isup2.hkl
Contains datablock I

mol

MDL mol file https://doi.org/10.1107/S0108270111017690/dn3162Isup3.mol
Supplementary material

CCDC reference: 833397

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

µ-4,4'-Bipyridine-κ2N:N'-bis[triaqua(4,4'-bipyridine- κN)cadmium(II)] bis(3-aminobenzoate) bis(perchlorate) dihydrate top
Crystal data top
[Cd2(C10H8N2)5(H2O)6](C7H6NO2)2(ClO4)2·2H2OF(000) = 1652
Mr = 1621.00Dx = 1.603 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5600 reflections
a = 7.4436 (1) Åθ = 1.3–28.0°
b = 19.0015 (4) ŵ = 0.80 mm1
c = 23.7517 (5) ÅT = 123 K
β = 91.686 (1)°Block, colourless
V = 3357.98 (11) Å30.25 × 0.19 × 0.16 mm
Z = 2
Data collection top
Bruker APEXII area-detector
diffractometer
6746 independent reflections
Radiation source: fine-focus sealed tube5834 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
φ and ω scansθmax = 26.4°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008)
h = 98
Tmin = 0.826, Tmax = 0.883k = 2123
29403 measured reflectionsl = 2529
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)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0253P)2 + 2.5909P]
where P = (Fo2 + 2Fc2)/3
6746 reflections(Δ/σ)max = 0.002
526 parametersΔρmax = 0.47 e Å3
26 restraintsΔρmin = 0.64 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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cd10.31031 (2)0.278662 (8)0.463427 (6)0.01969 (6)
O1W0.0201 (2)0.32526 (8)0.47221 (7)0.0316 (4)
H1W0.02970.35840.45540.047*
H2W0.03330.31210.50050.047*
O2W0.4397 (2)0.38428 (9)0.46096 (8)0.0415 (5)
H3W0.38130.42130.46390.062*
H4W0.54130.39390.44910.062*
O3W0.5985 (2)0.23019 (8)0.46636 (7)0.0265 (4)
H5W0.67170.24660.49020.040*
H6W0.65140.22770.43570.040*
N10.2722 (3)0.26620 (9)0.36533 (8)0.0232 (4)
N20.3223 (3)0.22475 (11)0.06897 (8)0.0299 (5)
N30.3213 (3)0.28227 (9)0.56321 (8)0.0251 (4)
N40.2315 (3)0.28213 (10)0.85999 (8)0.0299 (5)
N50.2011 (2)0.16426 (9)0.46961 (7)0.0209 (4)
C10.2457 (3)0.32100 (12)0.33039 (10)0.0256 (5)
H10.22480.36600.34630.031*
C20.2474 (3)0.31496 (12)0.27244 (9)0.0250 (5)
H20.22770.35520.24930.030*
C30.2784 (3)0.24931 (12)0.24798 (9)0.0214 (5)
C40.2991 (3)0.19205 (12)0.28448 (9)0.0251 (5)
H40.31500.14600.26990.030*
C50.2964 (3)0.20278 (12)0.34173 (10)0.0261 (5)
H50.31240.16330.36590.031*
C60.2925 (3)0.24084 (12)0.18611 (9)0.0219 (5)
C70.3565 (3)0.29507 (12)0.15256 (10)0.0259 (5)
H70.39130.33880.16900.031*
C80.3687 (3)0.28473 (13)0.09541 (10)0.0304 (5)
H80.41260.32240.07340.036*
C90.2608 (3)0.17261 (13)0.10138 (10)0.0299 (5)
H90.22670.12960.08380.036*
C100.2444 (3)0.17827 (12)0.15897 (10)0.0259 (5)
H100.20060.13970.18000.031*
C110.0260 (3)0.15288 (12)0.45943 (10)0.0244 (5)
H110.04440.19010.44370.029*
C120.0577 (3)0.09004 (11)0.47062 (10)0.0249 (5)
H120.18290.08460.46280.030*
C130.0423 (3)0.03443 (11)0.49352 (9)0.0201 (5)
C140.2247 (3)0.04597 (11)0.50309 (10)0.0251 (5)
H140.29870.00950.51830.030*
C150.2981 (3)0.11044 (11)0.49041 (9)0.0236 (5)
H150.42360.11700.49670.028*
C160.2541 (3)0.33801 (12)0.59040 (9)0.0255 (5)
H160.21700.37780.56880.031*
C170.2363 (3)0.34034 (11)0.64802 (9)0.0246 (5)
H170.18900.38110.66530.030*
C180.2883 (3)0.28237 (11)0.68076 (9)0.0213 (5)
C190.3591 (3)0.22472 (11)0.65253 (10)0.0244 (5)
H190.39690.18410.67300.029*
C200.3739 (3)0.22690 (12)0.59493 (10)0.0259 (5)
H200.42390.18730.57660.031*
C210.2699 (3)0.28205 (11)0.74269 (10)0.0227 (5)
C220.2840 (3)0.34391 (12)0.77394 (10)0.0293 (5)
H220.30730.38740.75580.035*
C230.2638 (3)0.34150 (13)0.83142 (10)0.0332 (6)
H230.27330.38430.85200.040*
C240.2198 (3)0.22254 (13)0.82968 (10)0.0300 (5)
H240.19810.17970.84900.036*
C250.2375 (3)0.22016 (12)0.77217 (10)0.0273 (5)
H250.22770.17660.75270.033*
O10.7790 (2)0.42654 (9)0.43078 (7)0.0355 (4)
O20.9922 (3)0.48125 (14)0.38445 (9)0.0673 (7)
C260.8366 (3)0.45907 (13)0.38849 (11)0.0316 (6)0.64
C270.7223 (9)0.4677 (6)0.3351 (3)0.0260 (16)0.64
C280.5403 (7)0.4820 (2)0.3370 (2)0.0265 (11)0.64
H280.48600.48660.37260.032*0.64
C290.4330 (12)0.4902 (6)0.2869 (3)0.0262 (19)0.64
C300.5172 (10)0.4824 (3)0.2360 (3)0.0307 (14)0.64
H300.44810.48670.20190.037*0.64
C310.6994 (8)0.4687 (2)0.23355 (19)0.0348 (10)0.64
H310.75330.46360.19800.042*0.64
C320.8033 (8)0.4623 (3)0.2825 (2)0.0317 (12)0.64
H320.92890.45420.28060.038*0.64
N60.2548 (5)0.50767 (18)0.28831 (15)0.0330 (8)0.64
H6A0.188 (5)0.501 (2)0.2576 (11)0.040*0.64
H6B0.197 (5)0.500 (2)0.3195 (10)0.040*0.64
C26'0.8366 (3)0.45907 (13)0.38849 (11)0.0316 (6)0.36
C27'0.6880 (19)0.4751 (13)0.3463 (5)0.0260 (16)0.36
C28'0.7224 (12)0.4660 (5)0.2906 (4)0.029 (2)0.36
H28'0.84070.45420.27990.035*0.36
C29'0.5846 (14)0.4737 (6)0.2483 (5)0.028 (2)0.36
C30'0.419 (2)0.4925 (13)0.2674 (6)0.038 (4)0.36
H30'0.32320.49900.24040.045*0.36
C31'0.3827 (10)0.5024 (3)0.3237 (4)0.0320 (17)0.36
H31'0.26560.51590.33450.038*0.36
C32'0.5174 (11)0.4928 (4)0.3644 (4)0.0256 (17)0.36
H32'0.49430.49800.40330.031*0.36
N6'0.6121 (10)0.4599 (4)0.1934 (3)0.0431 (16)0.36
H6'10.526 (8)0.480 (4)0.172 (3)0.052*0.36
H6'20.726 (4)0.464 (5)0.184 (4)0.052*0.36
Cl10.09831 (10)0.47981 (3)0.12530 (3)0.03987 (16)
O30.0727 (3)0.44133 (11)0.17691 (8)0.0561 (6)
O40.0576 (4)0.52103 (14)0.11161 (10)0.0752 (8)
O50.1284 (3)0.43147 (10)0.08081 (9)0.0538 (5)
O60.2501 (4)0.52602 (12)0.13228 (10)0.0765 (8)
O4W0.2417 (3)0.49913 (13)0.46777 (11)0.0576 (7)
H7W0.213 (6)0.519 (2)0.4954 (18)0.086*
H8W0.157 (5)0.491 (2)0.4480 (17)0.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.02180 (9)0.02047 (9)0.01688 (9)0.00327 (6)0.00201 (6)0.00091 (6)
O1W0.0289 (9)0.0357 (9)0.0305 (9)0.0078 (7)0.0060 (7)0.0116 (7)
O2W0.0347 (10)0.0247 (9)0.0660 (13)0.0087 (8)0.0164 (9)0.0025 (9)
O3W0.0214 (8)0.0389 (9)0.0194 (8)0.0015 (7)0.0009 (6)0.0028 (7)
N10.0269 (10)0.0233 (10)0.0194 (10)0.0018 (8)0.0012 (8)0.0012 (7)
N20.0313 (11)0.0388 (12)0.0199 (11)0.0037 (9)0.0028 (9)0.0036 (9)
N30.0269 (10)0.0263 (10)0.0221 (10)0.0028 (8)0.0021 (8)0.0020 (8)
N40.0299 (11)0.0383 (12)0.0215 (11)0.0004 (9)0.0016 (9)0.0010 (9)
N50.0234 (10)0.0209 (9)0.0185 (10)0.0039 (8)0.0001 (8)0.0015 (7)
C10.0303 (12)0.0214 (11)0.0251 (13)0.0004 (9)0.0014 (10)0.0002 (9)
C20.0316 (13)0.0218 (11)0.0214 (12)0.0023 (9)0.0009 (10)0.0025 (9)
C30.0180 (11)0.0251 (11)0.0212 (12)0.0021 (9)0.0007 (9)0.0004 (9)
C40.0331 (13)0.0196 (11)0.0228 (13)0.0005 (9)0.0020 (10)0.0017 (9)
C50.0341 (13)0.0215 (11)0.0228 (13)0.0010 (10)0.0026 (10)0.0043 (9)
C60.0181 (11)0.0276 (12)0.0202 (12)0.0034 (9)0.0005 (9)0.0001 (9)
C70.0297 (12)0.0255 (12)0.0225 (13)0.0005 (9)0.0010 (10)0.0005 (9)
C80.0324 (13)0.0353 (14)0.0236 (13)0.0008 (11)0.0039 (10)0.0046 (10)
C90.0304 (13)0.0319 (13)0.0274 (13)0.0005 (10)0.0014 (10)0.0079 (10)
C100.0276 (12)0.0257 (12)0.0246 (13)0.0008 (9)0.0015 (10)0.0006 (9)
C110.0221 (11)0.0238 (11)0.0272 (13)0.0001 (9)0.0016 (9)0.0055 (9)
C120.0200 (11)0.0247 (12)0.0297 (13)0.0022 (9)0.0013 (9)0.0047 (10)
C130.0238 (11)0.0212 (11)0.0154 (11)0.0014 (9)0.0004 (9)0.0007 (8)
C140.0240 (12)0.0200 (11)0.0309 (13)0.0002 (9)0.0043 (10)0.0026 (9)
C150.0207 (11)0.0243 (11)0.0257 (13)0.0040 (9)0.0032 (9)0.0004 (9)
C160.0303 (12)0.0239 (12)0.0222 (12)0.0016 (10)0.0005 (10)0.0020 (9)
C170.0282 (12)0.0218 (11)0.0239 (12)0.0004 (9)0.0037 (10)0.0036 (9)
C180.0200 (11)0.0236 (11)0.0202 (12)0.0045 (9)0.0011 (9)0.0013 (9)
C190.0243 (12)0.0242 (11)0.0246 (13)0.0005 (9)0.0005 (9)0.0002 (9)
C200.0273 (12)0.0246 (12)0.0258 (13)0.0015 (9)0.0010 (10)0.0041 (10)
C210.0204 (11)0.0249 (12)0.0226 (12)0.0005 (9)0.0013 (9)0.0000 (9)
C220.0376 (14)0.0249 (12)0.0253 (13)0.0064 (10)0.0024 (11)0.0017 (10)
C230.0420 (15)0.0338 (14)0.0239 (13)0.0037 (11)0.0022 (11)0.0069 (10)
C240.0344 (13)0.0299 (13)0.0258 (13)0.0027 (10)0.0022 (11)0.0074 (10)
C250.0322 (13)0.0235 (12)0.0262 (13)0.0001 (10)0.0013 (10)0.0009 (10)
O10.0363 (10)0.0351 (10)0.0353 (10)0.0036 (8)0.0022 (8)0.0067 (8)
O20.0323 (11)0.123 (2)0.0467 (13)0.0245 (12)0.0048 (10)0.0212 (13)
C260.0282 (13)0.0335 (13)0.0329 (14)0.0005 (10)0.0007 (11)0.0007 (11)
C270.027 (3)0.019 (3)0.031 (3)0.002 (2)0.000 (3)0.000 (3)
C280.031 (3)0.027 (2)0.023 (3)0.0065 (17)0.006 (2)0.000 (2)
C290.034 (3)0.018 (3)0.027 (5)0.004 (2)0.009 (4)0.002 (4)
C300.035 (4)0.024 (3)0.033 (4)0.003 (3)0.000 (3)0.005 (2)
C310.048 (3)0.027 (2)0.029 (3)0.001 (2)0.008 (2)0.0005 (17)
C320.033 (3)0.029 (2)0.033 (3)0.002 (3)0.005 (3)0.0024 (18)
N60.031 (2)0.0359 (18)0.032 (2)0.0014 (15)0.0019 (16)0.0022 (15)
C26'0.0282 (13)0.0335 (13)0.0329 (14)0.0005 (10)0.0007 (11)0.0007 (11)
C27'0.027 (3)0.019 (3)0.031 (3)0.002 (2)0.000 (3)0.000 (3)
C28'0.024 (5)0.019 (4)0.044 (7)0.000 (4)0.002 (5)0.004 (3)
C29'0.025 (7)0.025 (5)0.032 (6)0.003 (5)0.003 (5)0.001 (4)
C30'0.044 (7)0.031 (5)0.038 (11)0.010 (4)0.005 (8)0.008 (9)
C31'0.027 (4)0.015 (3)0.053 (6)0.004 (3)0.000 (4)0.011 (3)
C32'0.029 (4)0.019 (4)0.028 (5)0.002 (3)0.005 (4)0.009 (4)
N6'0.045 (4)0.053 (4)0.031 (4)0.001 (3)0.007 (3)0.005 (3)
Cl10.0533 (4)0.0340 (3)0.0315 (4)0.0004 (3)0.0120 (3)0.0001 (3)
O30.0729 (15)0.0559 (13)0.0387 (12)0.0130 (11)0.0097 (11)0.0122 (10)
O40.0855 (18)0.0884 (18)0.0511 (14)0.0487 (15)0.0075 (13)0.0035 (13)
O50.0704 (15)0.0392 (11)0.0517 (13)0.0038 (10)0.0012 (11)0.0091 (9)
O60.112 (2)0.0627 (15)0.0527 (14)0.0463 (14)0.0322 (14)0.0181 (12)
O4W0.0419 (13)0.0631 (15)0.0668 (17)0.0129 (11)0.0162 (11)0.0307 (12)
Geometric parameters (Å, º) top
Cd1—O2W2.2275 (16)C17—C181.396 (3)
Cd1—N52.3269 (17)C17—H170.9500
Cd1—O3W2.3336 (15)C18—C191.396 (3)
Cd1—O1W2.3499 (16)C18—C211.481 (3)
Cd1—N12.3509 (18)C19—C201.376 (3)
Cd1—N32.3699 (19)C19—H190.9500
O1W—H1W0.8274C20—H200.9500
O1W—H2W0.8294C21—C221.393 (3)
O2W—H3W0.8315C21—C251.393 (3)
O2W—H4W0.8349C22—C231.379 (3)
O3W—H5W0.8340C22—H220.9500
O3W—H6W0.8393C23—H230.9500
N1—C11.342 (3)C24—C251.377 (3)
N1—C51.343 (3)C24—H240.9500
N2—C81.342 (3)C25—H250.9500
N2—C91.343 (3)O1—C261.265 (3)
N3—C161.345 (3)O2—C261.239 (3)
N3—C201.346 (3)C26—C271.516 (6)
N4—C231.342 (3)C27—C281.384 (8)
N4—C241.343 (3)C27—C321.407 (8)
N5—C111.337 (3)C28—C291.423 (10)
N5—C151.338 (3)C28—H280.9500
C1—C21.382 (3)C29—N61.369 (9)
C1—H10.9500C29—C301.386 (9)
C2—C31.398 (3)C30—C311.384 (7)
C2—H20.9500C30—H300.9500
C3—C41.397 (3)C31—C321.382 (8)
C3—C61.485 (3)C31—H310.9500
C4—C51.376 (3)C32—H320.9500
C4—H40.9500N6—H6A0.880 (10)
C5—H50.9500N6—H6B0.881 (10)
C6—C101.394 (3)C27'—C28'1.366 (14)
C6—C71.395 (3)C27'—C32'1.394 (14)
C7—C81.377 (3)C28'—C29'1.422 (12)
C7—H70.9500C28'—H28'0.9500
C8—H80.9500C29'—N6'1.351 (13)
C9—C101.381 (3)C29'—C30'1.376 (14)
C9—H90.9500C30'—C31'1.386 (13)
C10—H100.9500C30'—H30'0.9500
C11—C121.376 (3)C31'—C32'1.383 (11)
C11—H110.9500C31'—H31'0.9500
C12—C131.394 (3)C32'—H32'0.9500
C12—H120.9500N6'—H6'10.882 (10)
C13—C141.388 (3)N6'—H6'20.882 (10)
C13—C13i1.488 (4)Cl1—O51.423 (2)
C14—C151.378 (3)Cl1—O41.430 (2)
C14—H140.9500Cl1—O61.437 (2)
C15—H150.9500Cl1—O31.445 (2)
C16—C171.379 (3)O4W—H7W0.79 (4)
C16—H160.9500O4W—H8W0.79 (4)
O2W—Cd1—N5174.51 (7)C16—C17—C18119.6 (2)
O2W—Cd1—O3W87.63 (6)C16—C17—H17120.2
N5—Cd1—O3W87.24 (6)C18—C17—H17120.2
O2W—Cd1—O1W93.56 (6)C19—C18—C17117.0 (2)
N5—Cd1—O1W91.30 (6)C19—C18—C21121.4 (2)
O3W—Cd1—O1W173.12 (5)C17—C18—C21121.61 (19)
O2W—Cd1—N195.99 (7)C20—C19—C18119.8 (2)
N5—Cd1—N186.35 (6)C20—C19—H19120.1
O3W—Cd1—N194.23 (6)C18—C19—H19120.1
O1W—Cd1—N192.38 (6)N3—C20—C19123.3 (2)
O2W—Cd1—N389.89 (7)N3—C20—H20118.3
N5—Cd1—N388.04 (6)C19—C20—H20118.3
O3W—Cd1—N388.68 (6)C22—C21—C25117.1 (2)
O1W—Cd1—N384.55 (6)C22—C21—C18121.2 (2)
N1—Cd1—N3173.54 (6)C25—C21—C18121.7 (2)
Cd1—O1W—H1W130.1C23—C22—C21119.4 (2)
Cd1—O1W—H2W115.0C23—C22—H22120.3
H1W—O1W—H2W113.7C21—C22—H22120.3
Cd1—O2W—H3W122.2N4—C23—C22123.7 (2)
Cd1—O2W—H4W127.1N4—C23—H23118.1
H3W—O2W—H4W108.9C22—C23—H23118.1
Cd1—O3W—H5W117.1N4—C24—C25123.6 (2)
Cd1—O3W—H6W116.8N4—C24—H24118.2
H5W—O3W—H6W107.2C25—C24—H24118.2
C1—N1—C5117.20 (19)C24—C25—C21119.6 (2)
C1—N1—Cd1123.07 (15)C24—C25—H25120.2
C5—N1—Cd1119.35 (14)C21—C25—H25120.2
C8—N2—C9116.5 (2)O2—C26—O1124.5 (2)
C16—N3—C20116.9 (2)O2—C26—C27113.7 (4)
C16—N3—Cd1120.06 (15)O1—C26—C27121.5 (5)
C20—N3—Cd1122.56 (15)C28—C27—C32119.4 (5)
C23—N4—C24116.6 (2)C28—C27—C26121.3 (5)
C11—N5—C15117.13 (19)C32—C27—C26119.4 (5)
C11—N5—Cd1118.71 (14)C27—C28—C29121.3 (5)
C15—N5—Cd1123.48 (14)C27—C28—H28119.4
N1—C1—C2123.1 (2)C29—C28—H28119.4
N1—C1—H1118.5N6—C29—C30120.7 (7)
C2—C1—H1118.5N6—C29—C28121.8 (6)
C1—C2—C3119.6 (2)C30—C29—C28117.5 (6)
C1—C2—H2120.2C31—C30—C29121.7 (7)
C3—C2—H2120.2C31—C30—H30119.2
C4—C3—C2117.0 (2)C29—C30—H30119.2
C4—C3—C6121.3 (2)C29—C30—H6'1155 (2)
C2—C3—C6121.7 (2)C32—C31—C30120.4 (5)
C5—C4—C3119.6 (2)C32—C31—H31119.8
C5—C4—H4120.2C30—C31—H31119.8
C3—C4—H4120.2C32—C31—H6'2135 (2)
N1—C5—C4123.5 (2)C30—C31—H6'2104 (2)
N1—C5—H5118.3C31—C32—C27119.7 (5)
C4—C5—H5118.3C31—C32—H32120.1
C10—C6—C7116.9 (2)C27—C32—H32120.1
C10—C6—C3121.7 (2)C29—N6—H6A118 (3)
C7—C6—C3121.4 (2)C29—N6—H6B119 (3)
C8—C7—C6119.4 (2)H6A—N6—H6B113 (4)
C8—C7—H7120.3C28'—C27'—C32'121.8 (9)
C6—C7—H7120.3C27'—C28'—C29'121.3 (9)
N2—C8—C7124.0 (2)C27'—C28'—H28'119.4
N2—C8—H8118.0C29'—C28'—H28'119.4
C7—C8—H8118.0N6'—C29'—C30'122.1 (11)
N2—C9—C10123.5 (2)N6'—C29'—C28'122.3 (10)
N2—C9—H9118.3C30'—C29'—C28'115.5 (11)
C10—C9—H9118.3C29'—C30'—C31'123.6 (14)
C9—C10—C6119.7 (2)C29'—C30'—H30'118.2
C9—C10—H10120.2C31'—C30'—H30'118.2
C6—C10—H10120.2C32'—C31'—C30'120.0 (9)
N5—C11—C12123.4 (2)C32'—C31'—H6B138.4 (12)
N5—C11—H11118.3C30'—C31'—H6B98.5 (14)
C12—C11—H11118.3C32'—C31'—H31'120.0
C11—C12—C13119.6 (2)C30'—C31'—H31'120.0
C11—C12—H12120.2C31'—C32'—C27'117.8 (8)
C13—C12—H12120.2C31'—C32'—H32'121.1
C14—C13—C12116.9 (2)C27'—C32'—H32'121.1
C14—C13—C13i121.5 (2)C29'—N6'—H6'1110 (6)
C12—C13—C13i121.5 (2)C29'—N6'—H6'2113 (6)
C15—C14—C13119.8 (2)H6'1—N6'—H6'2120 (8)
C15—C14—H14120.1O5—Cl1—O4109.21 (14)
C13—C14—H14120.1O5—Cl1—O6109.88 (16)
N5—C15—C14123.1 (2)O4—Cl1—O6108.77 (17)
N5—C15—H15118.4O5—Cl1—O3109.33 (13)
C14—C15—H15118.4O4—Cl1—O3110.12 (15)
N3—C16—C17123.3 (2)O6—Cl1—O3109.52 (13)
N3—C16—H16118.3H7W—O4W—H8W111 (4)
C17—C16—H16118.3
O2W—Cd1—N1—C130.74 (18)C11—C12—C13—C13i179.8 (2)
N5—Cd1—N1—C1154.24 (18)C12—C13—C14—C150.5 (3)
O3W—Cd1—N1—C1118.80 (18)C13i—C13—C14—C15179.8 (2)
O1W—Cd1—N1—C163.09 (18)C11—N5—C15—C142.1 (3)
O2W—Cd1—N1—C5141.98 (17)Cd1—N5—C15—C14168.34 (17)
N5—Cd1—N1—C533.04 (17)C13—C14—C15—N51.0 (4)
O3W—Cd1—N1—C553.92 (17)C20—N3—C16—C170.5 (3)
O1W—Cd1—N1—C5124.19 (17)Cd1—N3—C16—C17172.10 (17)
O2W—Cd1—N3—C1652.33 (17)N3—C16—C17—C180.5 (3)
N5—Cd1—N3—C16132.75 (17)C16—C17—C18—C190.9 (3)
O3W—Cd1—N3—C16139.97 (17)C16—C17—C18—C21179.3 (2)
O1W—Cd1—N3—C1641.26 (16)C17—C18—C19—C200.3 (3)
O2W—Cd1—N3—C20135.51 (18)C21—C18—C19—C20179.9 (2)
N5—Cd1—N3—C2039.41 (18)C16—N3—C20—C191.2 (3)
O3W—Cd1—N3—C2047.87 (18)Cd1—N3—C20—C19171.23 (17)
O1W—Cd1—N3—C20130.90 (18)C18—C19—C20—N30.8 (4)
O3W—Cd1—N5—C11167.58 (17)C19—C18—C21—C22148.9 (2)
O1W—Cd1—N5—C1119.15 (17)C17—C18—C21—C2230.9 (3)
N1—Cd1—N5—C1173.16 (17)C19—C18—C21—C2531.2 (3)
N3—Cd1—N5—C11103.65 (17)C17—C18—C21—C25149.0 (2)
O3W—Cd1—N5—C1522.14 (17)C25—C21—C22—C230.7 (3)
O1W—Cd1—N5—C15151.13 (17)C18—C21—C22—C23179.2 (2)
N1—Cd1—N5—C15116.56 (18)C24—N4—C23—C220.3 (4)
N3—Cd1—N5—C1566.63 (18)C21—C22—C23—N40.3 (4)
C5—N1—C1—C21.9 (3)C23—N4—C24—C250.6 (4)
Cd1—N1—C1—C2171.01 (17)N4—C24—C25—C210.2 (4)
N1—C1—C2—C30.2 (4)C22—C21—C25—C240.5 (3)
C1—C2—C3—C42.5 (3)C18—C21—C25—C24179.4 (2)
C1—C2—C3—C6176.3 (2)O2—C26—C27—C28145.5 (8)
C2—C3—C4—C52.9 (3)O1—C26—C27—C2840.2 (11)
C6—C3—C4—C5175.9 (2)O2—C26—C27—C3233.3 (11)
C1—N1—C5—C41.5 (3)O1—C26—C27—C32141.0 (8)
Cd1—N1—C5—C4171.64 (18)C32—C27—C28—C291.2 (15)
C3—C4—C5—N10.9 (4)C26—C27—C28—C29180.0 (9)
C4—C3—C6—C1030.2 (3)C27—C28—C29—N6176.8 (9)
C2—C3—C6—C10151.1 (2)C27—C28—C29—C300.6 (14)
C4—C3—C6—C7149.1 (2)N6—C29—C30—C31176.3 (8)
C2—C3—C6—C729.6 (3)C28—C29—C30—C311.2 (14)
C10—C6—C7—C80.1 (3)C29—C30—C31—C320.1 (10)
C3—C6—C7—C8179.5 (2)C30—C31—C32—C271.9 (10)
C9—N2—C8—C70.0 (4)C28—C27—C32—C312.5 (14)
C6—C7—C8—N20.0 (4)C26—C27—C32—C31178.7 (6)
C8—N2—C9—C100.1 (3)C32'—C27'—C28'—C29'0 (3)
N2—C9—C10—C60.3 (4)C27'—C28'—C29'—N6'174.9 (16)
C7—C6—C10—C90.3 (3)C27'—C28'—C29'—C30'2 (2)
C3—C6—C10—C9179.6 (2)N6'—C29'—C30'—C31'175.4 (16)
C15—N5—C11—C121.8 (3)C28'—C29'—C30'—C31'1 (3)
Cd1—N5—C11—C12169.15 (18)C29'—C30'—C31'—C32'1 (3)
N5—C11—C12—C130.3 (4)C30'—C31'—C32'—C27'2 (2)
C11—C12—C13—C140.9 (3)C28'—C27'—C32'—C31'1 (3)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C30—H30···O60.952.313.228 (6)163
C11—H11···N4ii0.952.613.406 (3)142
C14—H14···O4iii0.952.503.262 (3)137
C23—H23···O4iv0.952.583.336 (3)137
C31—H31···O3v0.952.483.166 (6)129
O1W—H1W···O1vi0.832.002.791 (2)160
O1W—H2W···N2vii0.832.102.924 (3)177
O2W—H3W···O4W0.831.812.641 (3)176
O2W—H4W···O10.831.942.765 (2)171
O3W—H6W···N4viii0.841.922.750 (3)170
N6—H6A···O30.88 (1)2.37 (2)3.196 (4)157 (4)
N6—H6B···O2vi0.88 (1)2.23 (2)3.090 (4)166 (4)
N6—H61···O60.88 (1)2.41 (2)3.275 (7)167 (8)
N6—H62···O3v0.88 (1)2.63 (3)3.481 (8)162 (8)
O4W—H7W···O1ix0.79 (4)2.04 (4)2.801 (3)163 (4)
O4W—H8W···O2vi0.79 (4)1.93 (4)2.695 (3)165 (4)
Symmetry codes: (ii) x1/2, y+1/2, z1/2; (iii) x+1/2, y+1/2, z+1/2; (iv) x, y+1, z+1; (v) x+1, y, z; (vi) x1, y, z; (vii) x1/2, y+1/2, z+1/2; (viii) x+1/2, y+1/2, z1/2; (ix) x+1, y+1, z+1.
Table 3. ππ stacking interactions (Å, °) top
Cg1 is the centroid of the N1, C1–C5 ring. Cg2 is the centroid of the N2, C6–C10 ring. Cg3 is the centroid of the N3, C16–C20 ring. Cg4 is the centroid of the N4, C21–C24 ring.
CgICgJCgI···CgJaCgI···P(J)bCgJ···P(I)cSlippage
Cg1Cg4vii3.9576 (13)3.9353.9560.466
Cg1Cg4iii3.6423 (13)3.3673.3851.388
Cg2Cg3vii3.7461 (13)3.3193.3881.737
Cg3Cg2ii3.7245 (13)3.5283.4941.192
Symmetry codes: (ii) -1/2+x, 1/2-y, 1/2+z; (iii)1/2+x, 1/2-y,-1/2+z; (vii) -1/2+x, 1/2-y, -1/2+z.

Notes: (a) Distance between centroids. (b) Perpendicular distance of CgI on ring plan J. (c) Perpendicular distance of CgJ on ring plan I. Slippage = vertical displacement between ring centroids.
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds