A cadmium(II) coordination polymer with both polyrotaxane and polycatenane features constructed by a V-shaped semi-rigid ligand: synthesis and fluorescence properties

One of the most inter­esting phenomena in coordination polymers (CPs) is the co-existence of different interlaced motifs. However, CPs having two different interlaced motifs at the same time are still rare. Colourless block-shaped crystals of the two-dimensional polymer poly[[aqua­(μ₂-naphthalene-2,6-di­carboxyl­ato){μ₂-4,4′-[oxybis(4,1-phenyl­ene)]di­pyridine}cadmium(II)] monohydrate], {[Cd(C₁₂H₆O₄)(C₂₂H₁₆N₂O)(H₂O)]·H₂O}_n, (I), was synthesized under hydro­thermal conditions by the self-assembly of 4,4′-[oxybis(4,1-phenyl­ene)]di­pyridine (OPY) with Cd^II in the presence of naphthalene-2,6-di­carb­oxy­lic acid (H₂ndc). Each Cd^II ion is six-coordinated by two N atoms from the pyridine rings of two OPY ligands and by four O atoms, three of which are from two ndc²⁻ ligands and one of which is from a water mol­ecule. In (I), every two identical two-dimensional (2D) 6³ layers are inter­penetrated in a parallel fashion, resulting in an interesting 2D→2D framework with both polyrotaxane and polycatenane characteristics. The extension of these sheets into a three-dimensional supra­molecular net is via O—H...O hydrogen bonds. The solid-state photoluminescence properties of (I) are also discussed.

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015)'; molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: 'SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010)'.

Poly[[aqua(µ₂-naphthalene-2,6-dicarboxylato){µ₂-4,4'-[oxybis(4,1-phenylene)]dipyridine}cadmium(II)] monohydrate]

Crystal data

[Cd(C12H6O4)(C22H16N2O)(H2O)]·H2O	Z = 2
Mr = 686.97	F(000) = 696
Triclinic, P1	Dx = 1.622 Mg m^−3
a = 8.0730 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 12.4019 (3) Å	Cell parameters from 9590 reflections
c = 15.2718 (4) Å	θ = 5.6–72.5°
α = 106.744 (2)°	µ = 6.69 mm^−1
β = 101.979 (2)°	T = 293 K
γ = 96.647 (2)°	Block, clear light colourless
V = 1406.93 (6) Å^3	0.20 × 0.08 × 0.06 mm

Data collection

SuperNova, Dual, Cu at zero, Eos diffractometer	5101 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	5040 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.033
Detector resolution: 16.0733 pixels mm^-1	θmax = 68.2°, θmin = 5.6°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→12
Tmin = 0.553, Tmax = 0.669	l = −16→18
12758 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.029	H-atom parameters constrained
wR(F^2) = 0.077	w = 1/[σ^2(Fo^2) + (0.0497P)^2 + 0.6294P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
5101 reflections	Δρmax = 1.21 e Å^−3
397 parameters	Δρmin = −1.11 e Å^−3

Special details

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 > 2sigma(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
C11	1.5190 (3)	0.3022 (2)	0.79084 (18)	0.0280 (5)
C12	1.5722 (3)	0.4191 (2)	0.80932 (18)	0.0317 (5)
H12	1.6869	0.4528	0.8390	0.038*
C13	1.4568 (3)	0.4862 (2)	0.78411 (19)	0.0314 (5)
H13	1.4933	0.5647	0.7988	0.038*
C16	1.3468 (3)	0.2548 (2)	0.7466 (2)	0.0350 (6)
H16	1.3080	0.1773	0.7355	0.042*
C15	1.2314 (3)	0.3201 (2)	0.7187 (2)	0.0343 (6)
H15	1.1172	0.2864	0.6878	0.041*
C14	1.2877 (3)	0.4362 (2)	0.73716 (17)	0.0266 (5)
C1	0.3677 (3)	0.2492 (2)	0.28408 (18)	0.0326 (5)
H1	0.3585	0.2380	0.2203	0.039*
C2	0.5227 (3)	0.3067 (2)	0.34809 (19)	0.0321 (5)
H2	0.6144	0.3333	0.3270	0.039*
C3	0.5409 (3)	0.3247 (2)	0.44414 (18)	0.0283 (5)
C4	0.3965 (3)	0.2859 (2)	0.47063 (18)	0.0339 (5)
H4	0.4013	0.2978	0.5341	0.041*
C5	0.2452 (3)	0.2292 (2)	0.40209 (19)	0.0342 (5)
H5	0.1500	0.2045	0.4215	0.041*
C6	0.0957 (3)	−0.1571 (2)	0.2005 (2)	0.0318 (5)
H6	−0.0081	−0.1636	0.2177	0.038*
C7	0.2005 (3)	−0.2360 (2)	0.2114 (2)	0.0325 (5)
H7	0.1664	−0.2937	0.2351	0.039*
C8	0.3564 (3)	−0.2282 (2)	0.18669 (17)	0.0279 (5)
C9	0.3936 (3)	−0.1449 (2)	0.14620 (19)	0.0332 (5)
H9	0.4931	−0.1396	0.1249	0.040*
C10	0.2823 (3)	−0.0693 (2)	0.13740 (18)	0.0316 (5)
H10	0.3099	−0.0140	0.1099	0.038*
C17	1.0253 (3)	0.4629 (2)	0.64719 (18)	0.0288 (5)
C18	1.0197 (3)	0.3970 (2)	0.5564 (2)	0.0372 (6)
H18	1.1210	0.3815	0.5398	0.045*
C19	0.8622 (3)	0.3540 (2)	0.48996 (19)	0.0348 (6)
H19	0.8584	0.3096	0.4288	0.042*
C20	0.7097 (3)	0.3768 (2)	0.51421 (18)	0.0280 (5)
C21	0.7193 (3)	0.4463 (3)	0.60541 (19)	0.0380 (6)
H21	0.6187	0.4637	0.6220	0.046*
C22	0.8765 (4)	0.4902 (2)	0.67190 (19)	0.0377 (6)
H22	0.8816	0.5374	0.7324	0.045*
C23	0.0120 (3)	0.2293 (2)	0.09227 (17)	0.0280 (5)
C24	0.0294 (3)	0.3250 (2)	0.05041 (17)	0.0298 (5)
C25	0.1599 (4)	0.3370 (2)	0.00237 (18)	0.0321 (5)
H25	0.2341	0.2849	−0.0043	0.038*
C26	0.1764 (4)	0.4251 (2)	−0.03395 (19)	0.0334 (5)
H26	0.2617	0.4322	−0.0656	0.040*
C27	−0.0656 (3)	0.4944 (2)	0.02409 (17)	0.0291 (5)
C28	−0.0793 (3)	0.4019 (2)	0.06101 (18)	0.0312 (5)
H28	−0.1637	0.3935	0.0930	0.037*
C29	−0.2457 (3)	0.0626 (2)	0.31460 (17)	0.0297 (5)
C30	−0.2628 (3)	0.0246 (3)	0.54995 (18)	0.0353 (6)
H30	−0.1851	0.0263	0.6049	0.042*
C31	−0.2019 (3)	0.0460 (3)	0.47827 (19)	0.0335 (5)
H31	−0.0836	0.0615	0.4849	0.040*
C32	−0.3168 (3)	0.0449 (2)	0.39418 (17)	0.0262 (5)
C33	−0.4908 (3)	0.0241 (2)	0.38567 (17)	0.0274 (5)
H33	−0.5663	0.0257	0.3312	0.033*
C34	−0.5581 (3)	0.0002 (2)	0.45801 (16)	0.0253 (5)
Cd1	−0.01747 (2)	0.08014 (2)	0.19318 (2)	0.02295 (8)
N1	0.2295 (3)	0.20853 (19)	0.30941 (16)	0.0310 (4)
N2	0.1365 (3)	−0.07192 (17)	0.16656 (14)	0.0273 (4)
O1	0.1062 (3)	0.15554 (16)	0.07919 (13)	0.0350 (4)
O2	−0.0934 (3)	0.22903 (17)	0.14281 (15)	0.0380 (4)
O3	−0.0961 (3)	0.0418 (2)	0.31442 (14)	0.0444 (5)
O4	−0.3328 (3)	0.0946 (2)	0.25356 (16)	0.0562 (6)
O5	1.1816 (2)	0.50953 (15)	0.71500 (14)	0.0349 (4)
O7	−0.2292 (2)	−0.05376 (17)	0.07040 (14)	0.0374 (4)
H7B	−0.3159	−0.0233	0.0568	0.056*
H7C	−0.1894	−0.0758	0.0222	0.056*
O1W	0.5458 (3)	0.1397 (4)	0.0870 (2)	0.0871 (11)
H1WA	0.5907	0.2106	0.1086	0.131*
H1WB	0.5589	0.1112	0.1318	0.131*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0263 (12)	0.0285 (12)	0.0303 (12)	0.0078 (9)	0.0064 (9)	0.0107 (10)
C12	0.0243 (12)	0.0305 (13)	0.0356 (13)	0.0026 (9)	−0.0019 (9)	0.0113 (10)
C13	0.0294 (12)	0.0243 (11)	0.0353 (13)	0.0023 (10)	−0.0014 (10)	0.0093 (10)
C16	0.0266 (12)	0.0271 (12)	0.0509 (16)	0.0058 (10)	0.0081 (11)	0.0131 (11)
C15	0.0208 (11)	0.0300 (12)	0.0476 (15)	0.0022 (9)	0.0025 (10)	0.0111 (11)
C14	0.0247 (11)	0.0280 (11)	0.0265 (11)	0.0078 (9)	0.0047 (9)	0.0082 (9)
C1	0.0311 (13)	0.0382 (13)	0.0266 (12)	0.0024 (10)	0.0045 (10)	0.0111 (10)
C2	0.0275 (12)	0.0373 (13)	0.0322 (13)	0.0034 (10)	0.0073 (10)	0.0132 (11)
C3	0.0254 (12)	0.0282 (11)	0.0291 (12)	0.0083 (9)	0.0039 (10)	0.0070 (10)
C4	0.0284 (12)	0.0432 (14)	0.0271 (12)	0.0062 (11)	0.0071 (10)	0.0067 (11)
C5	0.0272 (12)	0.0412 (14)	0.0323 (13)	0.0049 (10)	0.0105 (10)	0.0075 (11)
C6	0.0236 (11)	0.0344 (13)	0.0434 (14)	0.0075 (10)	0.0107 (10)	0.0193 (11)
C7	0.0282 (12)	0.0325 (12)	0.0443 (15)	0.0074 (10)	0.0113 (11)	0.0214 (11)
C8	0.0258 (12)	0.0282 (12)	0.0284 (12)	0.0072 (9)	0.0034 (9)	0.0090 (10)
C9	0.0307 (13)	0.0396 (13)	0.0380 (14)	0.0118 (11)	0.0151 (11)	0.0189 (11)
C10	0.0345 (13)	0.0345 (13)	0.0333 (13)	0.0101 (10)	0.0119 (10)	0.0185 (11)
C17	0.0240 (11)	0.0254 (11)	0.0338 (13)	0.0057 (9)	0.0002 (10)	0.0094 (10)
C18	0.0241 (12)	0.0416 (14)	0.0417 (15)	0.0089 (11)	0.0089 (11)	0.0056 (12)
C19	0.0293 (13)	0.0378 (14)	0.0305 (13)	0.0059 (10)	0.0069 (10)	0.0013 (11)
C20	0.0249 (12)	0.0279 (11)	0.0292 (12)	0.0068 (9)	0.0032 (9)	0.0081 (9)
C21	0.0273 (13)	0.0500 (16)	0.0319 (13)	0.0154 (11)	0.0056 (10)	0.0039 (12)
C22	0.0330 (14)	0.0441 (15)	0.0291 (13)	0.0151 (11)	0.0031 (11)	0.0017 (11)
C23	0.0337 (12)	0.0244 (11)	0.0240 (11)	−0.0009 (9)	0.0015 (9)	0.0115 (9)
C24	0.0387 (13)	0.0251 (11)	0.0234 (11)	0.0006 (10)	0.0025 (10)	0.0105 (9)
C25	0.0371 (13)	0.0282 (12)	0.0308 (12)	0.0041 (10)	0.0078 (10)	0.0106 (10)
C26	0.0391 (14)	0.0322 (13)	0.0324 (13)	0.0061 (11)	0.0126 (11)	0.0135 (10)
C27	0.0326 (12)	0.0290 (12)	0.0240 (11)	0.0016 (9)	0.0057 (10)	0.0085 (9)
C28	0.0363 (13)	0.0305 (12)	0.0272 (12)	0.0016 (10)	0.0075 (10)	0.0119 (10)
C29	0.0385 (14)	0.0250 (11)	0.0278 (12)	0.0024 (10)	0.0164 (10)	0.0075 (9)
C30	0.0258 (12)	0.0576 (17)	0.0268 (12)	0.0096 (11)	0.0055 (10)	0.0205 (12)
C31	0.0206 (11)	0.0520 (15)	0.0334 (13)	0.0068 (10)	0.0101 (10)	0.0197 (12)
C32	0.0302 (12)	0.0296 (11)	0.0239 (11)	0.0083 (9)	0.0128 (10)	0.0108 (9)
C33	0.0284 (12)	0.0371 (13)	0.0214 (11)	0.0096 (10)	0.0077 (9)	0.0140 (9)
C34	0.0253 (11)	0.0332 (12)	0.0211 (11)	0.0091 (9)	0.0077 (9)	0.0118 (9)
Cd1	0.02565 (11)	0.02444 (11)	0.02224 (10)	0.00608 (7)	0.00697 (7)	0.01159 (7)
N1	0.0270 (10)	0.0334 (11)	0.0290 (11)	0.0044 (9)	0.0043 (8)	0.0072 (9)
N2	0.0256 (10)	0.0291 (10)	0.0282 (10)	0.0076 (8)	0.0042 (8)	0.0117 (8)
O1	0.0456 (11)	0.0332 (9)	0.0321 (9)	0.0107 (8)	0.0105 (8)	0.0179 (8)
O2	0.0436 (11)	0.0374 (10)	0.0458 (11)	0.0132 (8)	0.0170 (9)	0.0265 (9)
O3	0.0310 (10)	0.0710 (14)	0.0360 (10)	0.0033 (9)	0.0172 (8)	0.0209 (10)
O4	0.0786 (17)	0.0770 (16)	0.0455 (12)	0.0413 (14)	0.0369 (12)	0.0436 (12)
O5	0.0273 (9)	0.0263 (8)	0.0422 (10)	0.0075 (7)	−0.0048 (8)	0.0063 (7)
O7	0.0290 (9)	0.0455 (11)	0.0332 (10)	0.0085 (8)	0.0040 (7)	0.0081 (8)
O1W	0.0382 (13)	0.158 (3)	0.0738 (19)	0.0017 (17)	−0.0006 (13)	0.068 (2)

Geometric parameters (Å, º)

C11—C16	1.388 (4)	C20—C21	1.392 (4)
C11—C12	1.391 (4)	C21—C22	1.387 (4)
C11—C8^i	1.492 (3)	C21—H21	0.9300
C12—C13	1.387 (4)	C22—H22	0.9300
C12—H12	0.9300	C23—O1	1.255 (3)
C13—C14	1.380 (4)	C23—O2	1.262 (3)
C13—H13	0.9300	C23—C24	1.507 (3)
C16—C15	1.384 (4)	C24—C28	1.367 (4)
C16—H16	0.9300	C24—C25	1.421 (4)
C15—C14	1.385 (4)	C25—C26	1.366 (4)
C15—H15	0.9300	C25—H25	0.9300
C14—O5	1.383 (3)	C26—C27^ii	1.413 (4)
C1—N1	1.345 (3)	C26—H26	0.9300
C1—C2	1.384 (4)	C27—C26^ii	1.413 (4)
C1—H1	0.9300	C27—C28	1.420 (4)
C2—C3	1.392 (4)	C27—C27^ii	1.425 (5)
C2—H2	0.9300	C28—H28	0.9300
C3—C4	1.390 (4)	C29—O4	1.235 (3)
C3—C20	1.488 (3)	C29—O3	1.264 (3)
C4—C5	1.389 (4)	C29—C32	1.507 (3)
C4—H4	0.9300	C30—C31	1.368 (4)
C5—N1	1.339 (3)	C30—C34^iii	1.415 (3)
C5—H5	0.9300	C30—H30	0.9300
C6—N2	1.341 (3)	C31—C32	1.415 (4)
C6—C7	1.388 (4)	C31—H31	0.9300
C6—H6	0.9300	C32—C33	1.370 (4)
C7—C8	1.388 (4)	C33—C34	1.416 (3)
C7—H7	0.9300	C33—H33	0.9300
C8—C9	1.383 (4)	C34—C30^iii	1.415 (3)
C8—C11^i	1.492 (3)	C34—C34^iii	1.425 (4)
C9—C10	1.386 (4)	Cd1—O3	2.2321 (19)
C9—H9	0.9300	Cd1—O2	2.2940 (18)
C10—N2	1.342 (3)	Cd1—O7	2.3266 (19)
C10—H10	0.9300	Cd1—N2	2.362 (2)
C17—C18	1.380 (4)	Cd1—N1	2.415 (2)
C17—C22	1.382 (4)	Cd1—O1	2.5191 (18)
C17—O5	1.394 (3)	O7—H7B	0.8501
C18—C19	1.388 (4)	O7—H7C	0.8499
C18—H18	0.9300	O1W—H1WA	0.8501
C19—C20	1.393 (4)	O1W—H1WB	0.8499
C19—H19	0.9300
C16—C11—C12	118.0 (2)	O1—C23—O2	122.1 (2)
C16—C11—C8^i	120.5 (2)	O1—C23—C24	119.6 (2)
C12—C11—C8^i	121.5 (2)	O2—C23—C24	118.2 (2)
C13—C12—C11	121.0 (2)	C28—C24—C25	120.2 (2)
C13—C12—H12	119.5	C28—C24—C23	119.3 (2)
C11—C12—H12	119.5	C25—C24—C23	120.5 (2)
C14—C13—C12	119.8 (2)	C26—C25—C24	120.0 (3)
C14—C13—H13	120.1	C26—C25—H25	120.0
C12—C13—H13	120.1	C24—C25—H25	120.0
C15—C16—C11	121.5 (2)	C25—C26—C27^ii	120.9 (2)
C15—C16—H16	119.2	C25—C26—H26	119.5
C11—C16—H16	119.2	C27^ii—C26—H26	119.5
C16—C15—C14	119.4 (2)	C26^ii—C27—C28	122.3 (2)
C16—C15—H15	120.3	C26^ii—C27—C27^ii	119.5 (3)
C14—C15—H15	120.3	C28—C27—C27^ii	118.2 (3)
C13—C14—O5	115.9 (2)	C24—C28—C27	121.2 (2)
C13—C14—C15	120.1 (2)	C24—C28—H28	119.4
O5—C14—C15	123.9 (2)	C27—C28—H28	119.4
N1—C1—C2	123.4 (2)	O4—C29—O3	123.5 (2)
N1—C1—H1	118.3	O4—C29—C32	120.3 (2)
C2—C1—H1	118.3	O3—C29—C32	116.2 (2)
C1—C2—C3	119.8 (2)	C31—C30—C34^iii	121.1 (2)
C1—C2—H2	120.1	C31—C30—H30	119.4
C3—C2—H2	120.1	C34^iii—C30—H30	119.4
C4—C3—C2	116.8 (2)	C30—C31—C32	120.8 (2)
C4—C3—C20	121.7 (2)	C30—C31—H31	119.6
C2—C3—C20	121.4 (2)	C32—C31—H31	119.6
C5—C4—C3	119.9 (2)	C33—C32—C31	119.3 (2)
C5—C4—H4	120.1	C33—C32—C29	121.3 (2)
C3—C4—H4	120.1	C31—C32—C29	119.4 (2)
N1—C5—C4	123.2 (2)	C32—C33—C34	121.4 (2)
N1—C5—H5	118.4	C32—C33—H33	119.3
C4—C5—H5	118.4	C34—C33—H33	119.3
N2—C6—C7	123.4 (2)	C30^iii—C34—C33	122.6 (2)
N2—C6—H6	118.3	C30^iii—C34—C34^iii	118.3 (3)
C7—C6—H6	118.3	C33—C34—C34^iii	119.1 (3)
C8—C7—C6	119.6 (2)	O3—Cd1—O2	122.71 (8)
C8—C7—H7	120.2	O3—Cd1—O7	98.58 (8)
C6—C7—H7	120.2	O2—Cd1—O7	92.26 (7)
C9—C8—C7	117.0 (2)	O3—Cd1—N2	93.22 (8)
C9—C8—C11^i	122.4 (2)	O2—Cd1—N2	144.06 (7)
C7—C8—C11^i	120.5 (2)	O7—Cd1—N2	82.04 (7)
C8—C9—C10	119.9 (2)	O3—Cd1—N1	86.26 (8)
C8—C9—H9	120.0	O2—Cd1—N1	90.08 (8)
C10—C9—H9	120.0	O7—Cd1—N1	172.33 (7)
N2—C10—C9	123.3 (2)	N2—Cd1—N1	91.79 (7)
N2—C10—H10	118.4	O3—Cd1—O1	169.49 (7)
C9—C10—H10	118.4	O2—Cd1—O1	54.23 (7)
C18—C17—C22	120.8 (2)	O7—Cd1—O1	91.71 (7)
C18—C17—O5	121.2 (2)	N2—Cd1—O1	90.32 (7)
C22—C17—O5	118.0 (2)	N1—Cd1—O1	83.74 (7)
C17—C18—C19	119.7 (2)	C5—N1—C1	116.8 (2)
C17—C18—H18	120.1	C5—N1—Cd1	121.25 (17)
C19—C18—H18	120.1	C1—N1—Cd1	121.30 (17)
C18—C19—C20	120.5 (2)	C6—N2—C10	116.6 (2)
C18—C19—H19	119.7	C6—N2—Cd1	117.18 (17)
C20—C19—H19	119.7	C10—N2—Cd1	124.84 (16)
C21—C20—C19	118.6 (2)	C23—O1—Cd1	86.61 (14)
C21—C20—C3	121.3 (2)	C23—O2—Cd1	96.85 (15)
C19—C20—C3	120.1 (2)	C29—O3—Cd1	109.20 (17)
C22—C21—C20	121.0 (2)	C14—O5—C17	118.61 (19)
C22—C21—H21	119.5	Cd1—O7—H7B	109.4
C20—C21—H21	119.5	Cd1—O7—H7C	109.4
C17—C22—C21	119.2 (2)	H7B—O7—H7C	109.5
C17—C22—H22	120.4	H1WA—O1W—H1WB	109.5
C21—C22—H22	120.4
C16—C11—C12—C13	−0.2 (4)	O1—C23—C24—C25	−4.6 (4)
C8^i—C11—C12—C13	176.9 (2)	O2—C23—C24—C25	172.6 (2)
C11—C12—C13—C14	−2.2 (4)	C28—C24—C25—C26	−0.5 (4)
C12—C11—C16—C15	2.0 (4)	C23—C24—C25—C26	−178.9 (2)
C8^i—C11—C16—C15	−175.1 (3)	C24—C25—C26—C27^ii	0.4 (4)
C11—C16—C15—C14	−1.5 (4)	C25—C24—C28—C27	0.5 (4)
C12—C13—C14—O5	179.8 (2)	C23—C24—C28—C27	178.9 (2)
C12—C13—C14—C15	2.7 (4)	C26^ii—C27—C28—C24	179.9 (2)
C16—C15—C14—C13	−0.8 (4)	C27^ii—C27—C28—C24	−0.4 (4)
C16—C15—C14—O5	−177.8 (3)	C34^iii—C30—C31—C32	0.5 (4)
N1—C1—C2—C3	0.1 (4)	C30—C31—C32—C33	1.2 (4)
C1—C2—C3—C4	−2.1 (4)	C30—C31—C32—C29	−176.8 (3)
C1—C2—C3—C20	174.5 (2)	O4—C29—C32—C33	22.9 (4)
C2—C3—C4—C5	1.8 (4)	O3—C29—C32—C33	−156.3 (2)
C20—C3—C4—C5	−174.7 (2)	O4—C29—C32—C31	−159.1 (3)
C3—C4—C5—N1	0.4 (4)	O3—C29—C32—C31	21.6 (4)
N2—C6—C7—C8	0.2 (4)	C31—C32—C33—C34	−2.0 (4)
C6—C7—C8—C9	−4.1 (4)	C29—C32—C33—C34	175.9 (2)
C6—C7—C8—C11^i	172.1 (2)	C32—C33—C34—C30^iii	−178.3 (3)
C7—C8—C9—C10	4.0 (4)	C32—C33—C34—C34^iii	1.1 (4)
C11^i—C8—C9—C10	−172.1 (2)	C4—C5—N1—C1	−2.3 (4)
C8—C9—C10—N2	0.0 (4)	C4—C5—N1—Cd1	168.5 (2)
C22—C17—C18—C19	−2.4 (4)	C2—C1—N1—C5	2.1 (4)
O5—C17—C18—C19	−178.5 (2)	C2—C1—N1—Cd1	−168.7 (2)
C17—C18—C19—C20	0.0 (4)	C7—C6—N2—C10	3.8 (4)
C18—C19—C20—C21	1.9 (4)	C7—C6—N2—Cd1	−163.4 (2)
C18—C19—C20—C3	−176.4 (3)	C9—C10—N2—C6	−3.9 (4)
C4—C3—C20—C21	−36.6 (4)	C9—C10—N2—Cd1	162.2 (2)
C2—C3—C20—C21	147.0 (3)	O2—C23—O1—Cd1	−4.1 (2)
C4—C3—C20—C19	141.7 (3)	C24—C23—O1—Cd1	173.0 (2)
C2—C3—C20—C19	−34.6 (4)	O1—C23—O2—Cd1	4.5 (3)
C19—C20—C21—C22	−1.5 (4)	C24—C23—O2—Cd1	−172.62 (18)
C3—C20—C21—C22	176.8 (3)	O4—C29—O3—Cd1	2.7 (3)
C18—C17—C22—C21	2.8 (4)	C32—C29—O3—Cd1	−178.11 (16)
O5—C17—C22—C21	179.1 (3)	C13—C14—O5—C17	163.2 (2)
C20—C21—C22—C17	−0.9 (5)	C15—C14—O5—C17	−19.8 (4)
O1—C23—C24—C28	176.9 (2)	C18—C17—O5—C14	−58.4 (3)
O2—C23—C24—C28	−5.9 (4)	C22—C17—O5—C14	125.3 (3)

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x, −y+1, −z; (iii) −x−1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···O4^iv	0.85	1.96	2.767 (3)	158
O7—H7C···O1^v	0.85	1.88	2.714 (3)	167
O7—H7B···O1W^v	0.85	2.49	2.965 (3)	116
O7—H7B···O1W^vi	0.85	2.40	3.158 (4)	149
C5—H5···O3	0.93	2.55	3.159 (3)	123
C1—H1···O1	0.93	2.50	3.192 (3)	131

Symmetry codes: (iv) x+1, y, z; (v) −x, −y, −z; (vi) x−1, y, z.