Synthesis and characterization of a cadmium(II)-organic supra­molecular coordination compound based on the multifunctional 2-amino-5-sulfo­benzoic acid ligand

Much attention has been paid by chemists to the construction of supra­molecular coordination compounds based on the multifunctional ligand 5-sulfosalicylic acid (H₃SSA) due to the structural and biological inter­est of these compounds. However, no coordination compounds have been reported for the multifunctional amino-substituted sulfobenzoate ligand 2-amino-5-sulfo­benzoic acid (H₂asba). We expected that H₂asba could be a suitable building block for the assembly of supra­molecular networks due to its inter­esting structural characteristics. The reaction of cadmium(II) nitrate with H₂asba in the presence of the auxiliary flexible di­pyridyl­amide ligand N,N'-bis­[(pyridin-4-yl)meth­yl]oxamide (4bpme) under ambient conditions formed a new mixed-ligand coordination compound, namely bis­(3-amino-4-carb­oxy­benzene­sulfonato-[kappa]O¹)di­aqua­bis­{N,N'-bis­[(pyridin-4-yl)meth­yl]ox­amide-[kappa]N}cadmium(II)-N,N'-bis­[(pyridin-4-yl)meth­yl]oxamide-water (1/1/4), [Cd(C₇H₆NO₅S)₂(C₁₄H₁₄N₄O₂)₂(H₂O)₂]·C₁₄H₁₄N₄O₂·4H₂O, (1), which was characterized by single-crystal and powder X-ray diffraction analysis (PXRD), FT-IR spectroscopy, thermogravimetric analysis (TG), and UV-Vis and photoluminescence spectroscopic analyses in the solid state. The central Cd^II atom in (1) occupies a special position on a centre of inversion and exhibits a slightly distorted octa­hedral geometry, being coordinated by two N atoms from two monodentate 4bpme ligands, four O atoms from two monodentate 4-amino-3-carb­oxy­benzene­sulfonate (Hasba^-) ligands and two coordinated water mol­ecules. Inter­estingly, complex (1) further extends into a threefold polycatenated 0D[rightwards arrow]2D (0D is zero-dimensional and 2D is two-dimensional) interpenetrated supra­molecular two-dimensional (4,4) layer through inter­molecular hydrogen bonding. The inter­layer hydrogen bonding further links adjacent threefold polycatenated two-dimensional layers into a three-dimensional network. The optical properties of complex (1) indicate that it may be used as a potential indirect band gap semiconductor material. Complex (1) exhibits an irreversible dehydration-rehydration behaviour. The fluorescence properties have also been investigated in the solid state at room temperature.

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Bis(3-amino-4-carboxybenzenesulfonato-κO¹)diaquabis{N,N'-bis[(pyridin-4-yl)methyl]oxamide-κN}cadmium(II)–N,N'-bis[(pyridin-4-yl)methyl]oxamide–water (1/1/4)

Crystal data

[Cd(C7H6NO5S)2(C14H14N4O2)2(H2O)2]·C14H14N4O2·4H2O	Z = 1
Mr = 1463.78	F(000) = 756
Triclinic, P1	Dx = 1.548 Mg m^−3
Hall symbol: -P1	Mo Kα radiation, λ = 0.71073 Å
a = 10.8873 (12) Å	Cell parameters from 9883 reflections
b = 11.4736 (12) Å	θ = 2.5–27.5°
c = 13.4521 (15) Å	µ = 0.50 mm^−1
α = 87.806 (3)°	T = 293 K
β = 88.438 (3)°	Block, colourless
γ = 69.247 (3)°	0.25 × 0.20 × 0.15 mm
V = 1570.0 (3) Å^3

Data collection

Bruker APEXII area-detector diffractometer	7122 independent reflections
Radiation source: fine-focus sealed tube	6299 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.3 pixels mm^-1	θmax = 27.5°, θmin = 1.9°
φ and ω scans	h = −14→14
Absorption correction: multi-scan SADABS	k = −14→14
Tmin = 0.886, Tmax = 0.927	l = −17→16
23608 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.079	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.049P)^2 + 0.5959P] where P = (Fo^2 + 2Fc^2)/3
7122 reflections	(Δ/σ)max < 0.001
431 parameters	Δρmax = 0.54 e Å^−3
9 restraints	Δρmin = −0.52 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.08609 (17)	0.75195 (16)	−0.33652 (13)	0.0267 (4)
C2	0.02217 (18)	0.66425 (17)	−0.32628 (14)	0.0297 (4)
C3	0.00848 (19)	0.61690 (18)	−0.22982 (14)	0.0333 (4)
H3	−0.0351	0.5606	−0.2214	0.040*
C4	0.05798 (18)	0.65216 (17)	−0.14863 (14)	0.0300 (4)
H4	0.0470	0.6203	−0.0858	0.036*
C5	0.12483 (17)	0.73551 (16)	−0.15937 (13)	0.0253 (3)
C6	0.13684 (17)	0.78558 (16)	−0.25222 (13)	0.0263 (4)
H6	0.1795	0.8428	−0.2590	0.032*
C7	0.1033 (2)	0.80629 (18)	−0.43550 (14)	0.0327 (4)
C8	0.70739 (19)	0.61642 (17)	0.06845 (15)	0.0336 (4)
H8	0.7592	0.5528	0.0282	0.040*
C9	0.76566 (19)	0.68803 (17)	0.11402 (14)	0.0324 (4)
H9	0.8551	0.6720	0.1048	0.039*
C10	0.69097 (18)	0.78450 (15)	0.17387 (13)	0.0267 (4)
C11	0.55913 (19)	0.80238 (16)	0.18463 (14)	0.0302 (4)
H11	0.5052	0.8654	0.2243	0.036*
C12	0.50767 (18)	0.72651 (16)	0.13636 (14)	0.0304 (4)
H12	0.4184	0.7407	0.1441	0.036*
C13	0.7565 (2)	0.86203 (18)	0.22443 (15)	0.0338 (4)
H13A	0.7956	0.8185	0.2854	0.041*
H13B	0.8271	0.8683	0.1815	0.041*
C14	0.61362 (19)	1.01456 (17)	0.33667 (13)	0.0298 (4)
C15	0.5343 (2)	1.15399 (17)	0.34664 (14)	0.0316 (4)
C16	0.3789 (2)	1.30411 (19)	0.45589 (16)	0.0402 (5)
H16A	0.2935	1.3005	0.4741	0.048*
H16B	0.3680	1.3587	0.3973	0.048*
C17	0.4275 (2)	1.35853 (17)	0.53972 (14)	0.0334 (4)
C18	0.5591 (2)	1.3303 (2)	0.55632 (17)	0.0447 (5)
H18	0.6218	1.2741	0.5164	0.054*
C19	0.5972 (3)	1.3860 (2)	0.63254 (19)	0.0517 (6)
H19	0.6866	1.3663	0.6423	0.062*
C20	0.3874 (3)	1.4928 (2)	0.67703 (17)	0.0558 (7)
H20	0.3270	1.5493	0.7182	0.067*
C21	0.3400 (2)	1.4417 (2)	0.60283 (18)	0.0518 (6)
H21	0.2500	1.4629	0.5952	0.062*
C22	0.2425 (2)	0.0481 (2)	0.36350 (15)	0.0396 (5)
H22	0.2768	0.0756	0.4166	0.048*
C23	0.2560 (2)	0.0937 (2)	0.26845 (15)	0.0371 (4)
H23	0.2984	0.1509	0.2587	0.045*
C24	0.20651 (17)	0.05399 (17)	0.18835 (13)	0.0284 (4)
C25	0.1446 (2)	−0.0313 (2)	0.20738 (15)	0.0397 (5)
H25	0.1101	−0.0611	0.1557	0.048*
C26	0.1349 (2)	−0.0713 (2)	0.30430 (16)	0.0434 (5)
H26	0.0926	−0.1281	0.3164	0.052*
C27	0.21655 (18)	0.10326 (19)	0.08347 (13)	0.0334 (4)
H27A	0.1392	0.1080	0.0470	0.040*
H27B	0.2184	0.1870	0.0863	0.040*
C28	0.44615 (17)	0.04503 (17)	0.03265 (12)	0.0270 (4)
Cd1	0.5000	0.5000	0.0000	0.02595 (7)
N1	0.57979 (15)	0.63372 (13)	0.07909 (11)	0.0285 (3)
N2	0.67090 (17)	0.98639 (14)	0.24834 (11)	0.0323 (3)
H2	0.6565	1.0447	0.2032	0.048*
N3	0.46717 (17)	1.18011 (15)	0.43155 (12)	0.0351 (4)
H3A	0.4764	1.1203	0.4746	0.053*
N4	0.5132 (2)	1.46647 (17)	0.69309 (14)	0.0487 (5)
N5	0.18288 (17)	−0.03280 (16)	0.38145 (12)	0.0366 (4)
N6	0.33291 (14)	0.02541 (15)	0.03052 (11)	0.0293 (3)
H6A	0.3285	−0.0351	−0.0032	0.044*
N7	−0.02861 (19)	0.62481 (18)	−0.40401 (13)	0.0452 (4)
H7A	−0.0679	0.5722	−0.3938	0.068*
H7B	−0.0214	0.6524	−0.4634	0.068*
O1	0.30163 (15)	0.66064 (14)	−0.02385 (12)	0.0480 (4)
O2	0.09167 (14)	0.80146 (15)	0.02366 (10)	0.0440 (4)
O3	0.23235 (17)	0.87654 (14)	−0.08170 (11)	0.0470 (4)
O4	0.15928 (16)	0.88928 (14)	−0.43527 (10)	0.0411 (3)
H4A	0.1645	0.9150	−0.4924	0.062*
O5	0.0675 (2)	0.77610 (17)	−0.51241 (11)	0.0594 (5)
O6	0.46607 (14)	0.12562 (14)	0.07951 (10)	0.0390 (3)
O7	0.61981 (16)	0.93940 (13)	0.40575 (11)	0.0438 (4)
O8	0.53583 (17)	1.22861 (13)	0.28007 (11)	0.0482 (4)
O1W	0.58224 (15)	0.56164 (14)	−0.14583 (10)	0.0426 (3)
H1WA	0.5587	0.6395	−0.1508	0.064*
H1WB	0.5533	0.5310	−0.1966	0.064*
O2W	0.1393 (2)	0.5968 (2)	0.15763 (16)	0.0816 (6)
H2WB	0.1290	0.6700	0.1203	0.122*
H2WA	0.2234	0.5504	0.1404	0.122*
O3W	0.0494 (4)	0.6150 (3)	0.34867 (17)	0.1385 (15)
H3WA	0.0651	0.6191	0.2828	0.208*
H3WB	0.0545	0.6790	0.3869	0.208*
S1	0.19292 (4)	0.77277 (4)	−0.05318 (3)	0.02649 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0280 (9)	0.0268 (9)	0.0243 (8)	−0.0086 (7)	0.0000 (7)	−0.0005 (7)
C2	0.0304 (9)	0.0296 (9)	0.0293 (9)	−0.0104 (7)	−0.0022 (7)	−0.0033 (7)
C3	0.0375 (10)	0.0324 (10)	0.0355 (10)	−0.0194 (8)	−0.0008 (8)	−0.0003 (8)
C4	0.0341 (10)	0.0296 (9)	0.0260 (9)	−0.0113 (8)	0.0003 (7)	0.0030 (7)
C5	0.0257 (8)	0.0242 (8)	0.0238 (8)	−0.0060 (7)	−0.0023 (7)	−0.0017 (7)
C6	0.0257 (8)	0.0245 (8)	0.0282 (9)	−0.0082 (7)	0.0011 (7)	−0.0016 (7)
C7	0.0389 (10)	0.0329 (10)	0.0265 (9)	−0.0131 (8)	0.0017 (8)	−0.0029 (8)
C8	0.0335 (10)	0.0267 (9)	0.0384 (10)	−0.0070 (8)	−0.0009 (8)	−0.0102 (8)
C9	0.0286 (9)	0.0306 (9)	0.0382 (10)	−0.0101 (7)	−0.0009 (8)	−0.0075 (8)
C10	0.0358 (9)	0.0211 (8)	0.0240 (8)	−0.0110 (7)	−0.0032 (7)	−0.0005 (7)
C11	0.0341 (9)	0.0240 (9)	0.0310 (9)	−0.0080 (7)	0.0019 (7)	−0.0070 (7)
C12	0.0290 (9)	0.0265 (9)	0.0345 (9)	−0.0083 (7)	−0.0019 (7)	−0.0014 (7)
C13	0.0391 (10)	0.0331 (10)	0.0334 (10)	−0.0171 (8)	−0.0014 (8)	−0.0095 (8)
C14	0.0402 (10)	0.0279 (9)	0.0265 (9)	−0.0184 (8)	−0.0026 (7)	−0.0012 (7)
C15	0.0433 (11)	0.0276 (9)	0.0296 (9)	−0.0190 (8)	−0.0043 (8)	−0.0029 (8)
C16	0.0393 (11)	0.0339 (10)	0.0453 (12)	−0.0097 (9)	−0.0011 (9)	−0.0087 (9)
C17	0.0398 (10)	0.0231 (9)	0.0337 (10)	−0.0070 (8)	0.0028 (8)	−0.0015 (7)
C18	0.0393 (11)	0.0444 (12)	0.0503 (13)	−0.0136 (9)	0.0078 (10)	−0.0166 (10)
C19	0.0485 (13)	0.0528 (14)	0.0543 (14)	−0.0173 (11)	−0.0013 (11)	−0.0122 (11)
C20	0.0649 (16)	0.0412 (13)	0.0401 (12)	0.0089 (11)	−0.0016 (11)	−0.0137 (10)
C21	0.0423 (12)	0.0492 (13)	0.0469 (13)	0.0060 (10)	−0.0003 (10)	−0.0129 (11)
C22	0.0417 (11)	0.0511 (12)	0.0296 (9)	−0.0208 (10)	−0.0046 (8)	0.0023 (9)
C23	0.0355 (10)	0.0470 (12)	0.0335 (10)	−0.0209 (9)	−0.0015 (8)	0.0042 (9)
C24	0.0228 (8)	0.0319 (9)	0.0250 (8)	−0.0034 (7)	0.0040 (7)	0.0007 (7)
C25	0.0519 (12)	0.0426 (11)	0.0298 (10)	−0.0226 (10)	0.0021 (9)	−0.0054 (9)
C26	0.0606 (14)	0.0406 (11)	0.0371 (11)	−0.0282 (10)	0.0029 (10)	0.0008 (9)
C27	0.0249 (9)	0.0424 (11)	0.0271 (9)	−0.0053 (8)	0.0030 (7)	0.0049 (8)
C28	0.0265 (9)	0.0354 (9)	0.0185 (8)	−0.0107 (7)	−0.0001 (7)	0.0030 (7)
Cd1	0.03037 (11)	0.02300 (10)	0.02547 (10)	−0.01008 (7)	−0.00620 (7)	−0.00223 (7)
N1	0.0340 (8)	0.0224 (7)	0.0293 (8)	−0.0097 (6)	−0.0063 (6)	−0.0017 (6)
N2	0.0504 (10)	0.0259 (8)	0.0254 (7)	−0.0191 (7)	−0.0007 (7)	−0.0034 (6)
N3	0.0465 (10)	0.0267 (8)	0.0335 (8)	−0.0146 (7)	0.0036 (7)	−0.0030 (7)
N4	0.0711 (14)	0.0343 (9)	0.0365 (9)	−0.0127 (9)	−0.0062 (9)	−0.0034 (8)
N5	0.0433 (10)	0.0383 (9)	0.0272 (8)	−0.0137 (8)	0.0012 (7)	0.0033 (7)
N6	0.0252 (7)	0.0387 (9)	0.0237 (7)	−0.0113 (6)	0.0036 (6)	−0.0020 (6)
N7	0.0603 (12)	0.0564 (11)	0.0333 (9)	−0.0376 (10)	−0.0078 (8)	−0.0018 (8)
O1	0.0409 (8)	0.0403 (8)	0.0522 (9)	0.0003 (6)	−0.0192 (7)	−0.0026 (7)
O2	0.0395 (8)	0.0600 (10)	0.0296 (7)	−0.0133 (7)	0.0029 (6)	−0.0108 (7)
O3	0.0678 (10)	0.0474 (9)	0.0397 (8)	−0.0371 (8)	−0.0094 (7)	−0.0006 (7)
O4	0.0588 (9)	0.0484 (8)	0.0261 (7)	−0.0320 (7)	−0.0003 (6)	0.0062 (6)
O5	0.1040 (15)	0.0705 (11)	0.0254 (7)	−0.0573 (11)	−0.0048 (8)	0.0000 (7)
O6	0.0364 (7)	0.0479 (8)	0.0359 (7)	−0.0179 (6)	0.0042 (6)	−0.0126 (6)
O7	0.0619 (10)	0.0317 (7)	0.0348 (7)	−0.0142 (7)	0.0073 (7)	0.0050 (6)
O8	0.0784 (11)	0.0276 (7)	0.0365 (8)	−0.0171 (7)	0.0039 (7)	0.0034 (6)
O1W	0.0562 (9)	0.0400 (8)	0.0321 (7)	−0.0176 (7)	−0.0044 (7)	0.0046 (6)
O2W	0.0802 (14)	0.0853 (15)	0.0748 (13)	−0.0282 (12)	0.0282 (11)	0.0197 (11)
O3W	0.296 (4)	0.138 (2)	0.0589 (13)	−0.172 (3)	0.0531 (19)	−0.0370 (15)
S1	0.0272 (2)	0.0261 (2)	0.0249 (2)	−0.00740 (17)	−0.00423 (17)	−0.00164 (17)

Geometric parameters (Å, º)

C1—C6	1.400 (2)	C20—N4	1.316 (3)
C1—C2	1.413 (3)	C20—C21	1.376 (3)
C1—C7	1.484 (3)	C20—H20	0.9300
C2—N7	1.360 (2)	C21—H21	0.9300
C2—C3	1.412 (3)	C22—N5	1.320 (3)
C3—C4	1.366 (3)	C22—C23	1.387 (3)
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.393 (2)	C23—C24	1.379 (3)
C4—H4	0.9300	C23—H23	0.9300
C5—C6	1.377 (2)	C24—C25	1.384 (3)
C5—S1	1.7613 (17)	C24—C27	1.515 (2)
C6—H6	0.9300	C25—C26	1.379 (3)
C7—O5	1.219 (2)	C25—H25	0.9300
C7—O4	1.300 (2)	C26—N5	1.332 (3)
C8—N1	1.336 (2)	C26—H26	0.9300
C8—C9	1.372 (3)	C27—N6	1.452 (2)
C8—H8	0.9300	C27—H27A	0.9700
C9—C10	1.389 (3)	C27—H27B	0.9700
C9—H9	0.9300	C28—O6	1.222 (2)
C10—C11	1.380 (3)	C28—N6	1.331 (2)
C10—C13	1.512 (2)	C28—C28^i	1.539 (3)
C11—C12	1.379 (3)	Cd1—O1	2.3100 (14)
C11—H11	0.9300	Cd1—O1^ii	2.3100 (14)
C12—N1	1.334 (2)	Cd1—N1	2.3153 (15)
C12—H12	0.9300	Cd1—N1^ii	2.3153 (15)
C13—N2	1.444 (2)	Cd1—O1W^ii	2.3232 (14)
C13—H13A	0.9700	Cd1—O1W	2.3232 (14)
C13—H13B	0.9700	N2—H2	0.8600
C14—O7	1.230 (2)	N3—H3A	0.8600
C14—N2	1.323 (2)	N6—H6A	0.8600
C14—C15	1.534 (3)	N7—H7A	0.8600
C15—O8	1.219 (2)	N7—H7B	0.8600
C15—N3	1.325 (2)	O1—S1	1.4557 (15)
C16—N3	1.451 (3)	O2—S1	1.4488 (15)
C16—C17	1.504 (3)	O3—S1	1.4377 (15)
C16—H16A	0.9700	O4—H4A	0.8200
C16—H16B	0.9700	O1W—H1WA	0.8379
C17—C18	1.375 (3)	O1W—H1WB	0.8937
C17—C21	1.383 (3)	O2W—H2WB	0.9348
C18—C19	1.376 (3)	O2W—H2WA	0.9107
C18—H18	0.9300	O3W—H3WA	0.9010
C19—N4	1.331 (3)	O3W—H3WB	0.9299
C19—H19	0.9300
C6—C1—C2	119.36 (16)	N5—C22—C23	122.53 (19)
C6—C1—C7	119.58 (16)	N5—C22—H22	118.7
C2—C1—C7	121.04 (16)	C23—C22—H22	118.7
N7—C2—C3	118.43 (17)	C22—C23—C24	119.84 (18)
N7—C2—C1	123.50 (17)	C22—C23—H23	120.1
C3—C2—C1	118.06 (16)	C24—C23—H23	120.1
C4—C3—C2	121.35 (17)	C25—C24—C23	117.48 (17)
C4—C3—H3	119.3	C25—C24—C27	120.85 (17)
C2—C3—H3	119.3	C23—C24—C27	121.66 (17)
C3—C4—C5	120.47 (17)	C26—C25—C24	118.86 (19)
C3—C4—H4	119.8	C26—C25—H25	120.6
C5—C4—H4	119.8	C24—C25—H25	120.6
C6—C5—C4	119.44 (16)	N5—C26—C25	123.50 (19)
C6—C5—S1	121.85 (14)	N5—C26—H26	118.3
C4—C5—S1	118.71 (13)	C25—C26—H26	118.3
C5—C6—C1	121.27 (16)	N6—C27—C24	112.43 (15)
C5—C6—H6	119.4	N6—C27—H27A	109.1
C1—C6—H6	119.4	C24—C27—H27A	109.1
O5—C7—O4	121.63 (18)	N6—C27—H27B	109.1
O5—C7—C1	122.85 (18)	C24—C27—H27B	109.1
O4—C7—C1	115.51 (16)	H27A—C27—H27B	107.8
N1—C8—C9	123.12 (17)	O6—C28—N6	125.43 (16)
N1—C8—H8	118.4	O6—C28—C28^i	121.8 (2)
C9—C8—H8	118.4	N6—C28—C28^i	112.77 (19)
C8—C9—C10	119.93 (18)	O1—Cd1—O1^ii	180.00 (7)
C8—C9—H9	120.0	O1—Cd1—N1	90.11 (5)
C10—C9—H9	120.0	O1^ii—Cd1—N1	89.89 (5)
C11—C10—C9	116.87 (16)	O1—Cd1—N1^ii	89.89 (5)
C11—C10—C13	123.67 (16)	O1^ii—Cd1—N1^ii	90.11 (5)
C9—C10—C13	119.45 (17)	N1—Cd1—N1^ii	180.00 (6)
C12—C11—C10	119.83 (16)	O1—Cd1—O1W^ii	90.04 (6)
C12—C11—H11	120.1	O1^ii—Cd1—O1W^ii	89.96 (6)
C10—C11—H11	120.1	N1—Cd1—O1W^ii	93.98 (5)
N1—C12—C11	123.14 (17)	N1^ii—Cd1—O1W^ii	86.02 (5)
N1—C12—H12	118.4	O1—Cd1—O1W	89.96 (6)
C11—C12—H12	118.4	O1^ii—Cd1—O1W	90.04 (6)
N2—C13—C10	115.14 (16)	N1—Cd1—O1W	86.02 (5)
N2—C13—H13A	108.5	N1^ii—Cd1—O1W	93.98 (5)
C10—C13—H13A	108.5	O1W^ii—Cd1—O1W	180.00 (8)
N2—C13—H13B	108.5	C12—N1—C8	117.11 (15)
C10—C13—H13B	108.5	C12—N1—Cd1	124.64 (12)
H13A—C13—H13B	107.5	C8—N1—Cd1	118.25 (12)
O7—C14—N2	125.29 (18)	C14—N2—C13	122.82 (16)
O7—C14—C15	121.30 (17)	C14—N2—H2	118.6
N2—C14—C15	113.41 (15)	C13—N2—H2	118.6
O8—C15—N3	126.17 (18)	C15—N3—C16	123.54 (17)
O8—C15—C14	120.65 (17)	C15—N3—H3A	118.2
N3—C15—C14	113.17 (16)	C16—N3—H3A	118.2
N3—C16—C17	112.86 (17)	C20—N4—C19	116.7 (2)
N3—C16—H16A	109.0	C22—N5—C26	117.79 (17)
C17—C16—H16A	109.0	C28—N6—C27	121.91 (16)
N3—C16—H16B	109.0	C28—N6—H6A	119.0
C17—C16—H16B	109.0	C27—N6—H6A	119.0
H16A—C16—H16B	107.8	C2—N7—H7A	120.0
C18—C17—C21	117.1 (2)	C2—N7—H7B	120.0
C18—C17—C16	122.22 (18)	H7A—N7—H7B	120.0
C21—C17—C16	120.70 (19)	S1—O1—Cd1	167.77 (11)
C17—C18—C19	119.4 (2)	C7—O4—H4A	109.5
C17—C18—H18	120.3	Cd1—O1W—H1WA	111.0
C19—C18—H18	120.3	Cd1—O1W—H1WB	107.6
N4—C19—C18	123.7 (2)	H1WA—O1W—H1WB	111.3
N4—C19—H19	118.2	H2WB—O2W—H2WA	100.0
C18—C19—H19	118.2	H3WA—O3W—H3WB	117.7
N4—C20—C21	123.8 (2)	O3—S1—O2	113.39 (10)
N4—C20—H20	118.1	O3—S1—O1	113.74 (10)
C21—C20—H20	118.1	O2—S1—O1	109.50 (10)
C20—C21—C17	119.4 (2)	O3—S1—C5	106.64 (9)
C20—C21—H21	120.3	O2—S1—C5	106.68 (8)
C17—C21—H21	120.3	O1—S1—C5	106.36 (8)
C6—C1—C2—N7	−179.13 (18)	C24—C25—C26—N5	−0.4 (3)
C7—C1—C2—N7	−0.8 (3)	C25—C24—C27—N6	−88.4 (2)
C6—C1—C2—C3	2.0 (3)	C23—C24—C27—N6	92.9 (2)
C7—C1—C2—C3	−179.61 (17)	C11—C12—N1—C8	−0.7 (3)
N7—C2—C3—C4	179.59 (18)	C11—C12—N1—Cd1	178.17 (14)
C1—C2—C3—C4	−1.5 (3)	C9—C8—N1—C12	0.7 (3)
C2—C3—C4—C5	−0.6 (3)	C9—C8—N1—Cd1	−178.28 (15)
C3—C4—C5—C6	2.2 (3)	O1—Cd1—N1—C12	34.53 (15)
C3—C4—C5—S1	−177.28 (14)	O1^ii—Cd1—N1—C12	−145.47 (15)
C4—C5—C6—C1	−1.7 (3)	O1W^ii—Cd1—N1—C12	−55.51 (15)
S1—C5—C6—C1	177.81 (13)	O1W—Cd1—N1—C12	124.49 (15)
C2—C1—C6—C5	−0.5 (3)	O1—Cd1—N1—C8	−146.58 (14)
C7—C1—C6—C5	−178.87 (16)	O1^ii—Cd1—N1—C8	33.42 (14)
C6—C1—C7—O5	176.1 (2)	O1W^ii—Cd1—N1—C8	123.37 (14)
C2—C1—C7—O5	−2.3 (3)	O1W—Cd1—N1—C8	−56.63 (14)
C6—C1—C7—O4	−4.0 (3)	O7—C14—N2—C13	−4.2 (3)
C2—C1—C7—O4	177.61 (17)	C15—C14—N2—C13	176.32 (16)
N1—C8—C9—C10	−0.6 (3)	C10—C13—N2—C14	95.1 (2)
C8—C9—C10—C11	0.4 (3)	O8—C15—N3—C16	2.9 (3)
C8—C9—C10—C13	179.45 (18)	C14—C15—N3—C16	−176.31 (17)
C9—C10—C11—C12	−0.4 (3)	C17—C16—N3—C15	−112.7 (2)
C13—C10—C11—C12	−179.44 (17)	C21—C20—N4—C19	0.4 (4)
C10—C11—C12—N1	0.6 (3)	C18—C19—N4—C20	−0.3 (4)
C11—C10—C13—N2	−26.2 (3)	C23—C22—N5—C26	0.2 (3)
C9—C10—C13—N2	154.82 (17)	C25—C26—N5—C22	0.1 (3)
O7—C14—C15—O8	175.22 (19)	O6—C28—N6—C27	1.9 (3)
N2—C14—C15—O8	−5.3 (3)	C28^i—C28—N6—C27	−177.35 (17)
O7—C14—C15—N3	−5.5 (3)	C24—C27—N6—C28	−90.4 (2)
N2—C14—C15—N3	173.97 (16)	N1—Cd1—O1—S1	67.7 (5)
N3—C16—C17—C18	31.2 (3)	N1^ii—Cd1—O1—S1	−112.3 (5)
N3—C16—C17—C21	−149.9 (2)	O1W^ii—Cd1—O1—S1	161.7 (5)
C21—C17—C18—C19	−0.8 (3)	O1W—Cd1—O1—S1	−18.3 (5)
C16—C17—C18—C19	178.1 (2)	Cd1—O1—S1—O3	−27.8 (5)
C17—C18—C19—N4	0.5 (4)	Cd1—O1—S1—O2	−155.8 (4)
N4—C20—C21—C17	−0.7 (4)	Cd1—O1—S1—C5	89.3 (5)
C18—C17—C21—C20	0.9 (3)	C6—C5—S1—O3	11.42 (18)
C16—C17—C21—C20	−178.1 (2)	C4—C5—S1—O3	−169.11 (14)
N5—C22—C23—C24	−0.2 (3)	C6—C5—S1—O2	132.89 (15)
C22—C23—C24—C25	−0.1 (3)	C4—C5—S1—O2	−47.63 (16)
C22—C23—C24—C27	178.73 (18)	C6—C5—S1—O1	−110.29 (16)
C23—C24—C25—C26	0.4 (3)	C4—C5—S1—O1	69.19 (16)
C27—C24—C25—C26	−178.42 (19)

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O8^iii	0.84	2.27	2.882 (2)	130
N2—H2···O6^iv	0.86	2.58	3.187 (2)	129
N2—H2···O3^iii	0.86	2.35	3.063 (2)	141
O1W—H1WB···N4^v	0.89	1.81	2.702 (2)	173
O2W—H2WB···O2	0.93	1.89	2.810 (3)	167
N3—H3A···O7^vi	0.86	2.12	2.854 (2)	143
O2W—H2WA···O1W^ii	0.91	2.05	2.935 (3)	163
O4—H4A···N5^vii	0.82	1.81	2.628 (2)	178
O3W—H3WA···O2W	0.90	1.83	2.714 (3)	165
O3W—H3WB···O5^viii	0.93	1.83	2.737 (3)	166
N6—H6A···O3^ix	0.86	2.03	2.830 (2)	154
N7—H7A···O3W^x	0.86	2.15	2.907 (4)	147
N7—H7B···O5	0.86	2.06	2.692 (3)	129
C27—H27A···O2^x	0.97	2.55	3.475 (2)	159

Symmetry codes: (ii) −x+1, −y+1, −z; (iii) −x+1, −y+2, −z; (iv) x, y+1, z; (v) x, y−1, z−1; (vi) −x+1, −y+2, −z+1; (vii) x, y+1, z−1; (viii) x, y, z+1; (ix) x, y−1, z; (x) −x, −y+1, −z.