Substituent effects of two isophthalate derivatives on the construction of cadmium coordination polymers incorporating a dipyridyl ligand

In recent years, the design and construction of crystalline coordination com­plexes by the assembly of metal ions with multitopic ligands have attracted considerable attention because of the unique architectures and potential appli­cations of these compounds. Two new coordination polymers, namely poly[[μ-trans-1-(2-amino­pyridin-3-yl)-2-(pyridin-4-yl)ethene-κ²N:N′](μ₃-5-methyl­iso­phthalato-κ⁴O¹,O^1′:O³:O^3′)cadmium(II)], [Cd(C₉H₆O₄)(C₁₂H₁₁N₃)]_n or [Cd(5-Me-ip)(2-NH₂-3,4-bpe)]_n, (I), and poly[[μ-trans-1-(2-amino­pyridin-3-yl)-2-(pyri­din-4-yl)ethene-κ²N:N′](μ₂-5-hy­droxy­isophthalato-κ⁴O¹,O^1′:O³:O⁵)cadmium(II)], [Cd(C₈H₄O₅)(C₁₂H₁₁N₃)]_n or [Cd(5-HO-ip)(2-NH₂-3,4-bpe)]_n, (II), have been prepared hydro­thermally by the self-assembly of Cd(NO₃)₂·4H₂O and trans-1-(2-amino­pyridin-3-yl)-2-(pyridin-4-yl)ethene (2-NH₂-3,4-bpe) with two similar di­carb­oxy­lic acids, i.e. 5-methyl­isophthalic acid (5-Me-H₂ip) and 5-hy­droxy­isophthalic acid (5-HO-H₂ip). The coordination network of (I) is a two-dimensional sql net parallel to (101). Adjacent sql nets are further linked to form a three-dimensional supra­molecular framework via hydrogen-bonding inter­actions. Compound (II) is a two-dimensional (3,5)-connected coordination network parallel to (010) with the point symbol (6³)(5⁵6⁴7). As the other reactants and reaction conditions are the same, the structural differences between (I) and (II) are undoubtedly determined by the different substituent groups in the 5-position of isophthalic acid. Both (I) and (II) exhibit good thermal stabilities and photoluminescence properties.

Computing details

For both structures, data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: publCIF (Westrip, 2010).

Poly[[µ-trans-1-(2-aminopyridin-3-yl)-2-(pyridin-4-yl)ethene-κ²N:N'](µ₃-5-methylisophthalato-κ⁴O¹,O^1':O³:O^3')cadmium(II)] (I)

Crystal data

[Cd(C9H6O4)(C12H11N3)]	Z = 2
Mr = 487.79	F(000) = 488
Triclinic, P1	Dx = 1.670 Mg m^−3
a = 9.1432 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.439 (2) Å	Cell parameters from 18239 reflections
c = 10.872 (2) Å	θ = 2.9–27.5°
α = 73.04 (3)°	µ = 1.16 mm^−1
β = 83.23 (3)°	T = 223 K
γ = 78.38 (3)°	Block, yellow
V = 970.3 (4) Å^3	0.15 × 0.12 × 0.09 mm

Data collection

Bruker SMART CCD area detector diffractometer	4098 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
phi and ω scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
Tmin = 0.853, Tmax = 0.921	k = −13→12
18239 measured reflections	l = −14→14
4439 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.020	H-atom parameters constrained
wR(F^2) = 0.047	w = 1/[σ^2(Fo^2) + (0.0223P)^2 + 0.2967P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
4439 reflections	Δρmax = 0.30 e Å^−3
263 parameters	Δρmin = −0.38 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cd1	0.56849 (2)	0.61041 (2)	0.12454 (2)	0.02469 (5)
N1	0.32820 (17)	0.65631 (15)	0.23650 (14)	0.0302 (3)
N2	−0.21538 (17)	0.60912 (16)	0.98484 (14)	0.0335 (3)
N3	0.36552 (19)	0.48024 (17)	0.42089 (15)	0.0395 (4)
H3A	0.4432	0.4432	0.3809	0.047*
H3B	0.3406	0.4401	0.5005	0.047*
O1	0.59215 (16)	0.39300 (12)	0.22758 (12)	0.0360 (3)
O2	0.56716 (16)	0.32934 (13)	0.05469 (12)	0.0373 (3)
O3	0.57903 (16)	−0.16824 (12)	0.11445 (12)	0.0354 (3)
O4	0.65823 (16)	−0.31769 (12)	0.29326 (13)	0.0387 (3)
C1	0.2436 (2)	0.7719 (2)	0.16999 (19)	0.0382 (4)
H1	0.2748	0.8107	0.0839	0.046*
C2	0.1156 (2)	0.8358 (2)	0.2205 (2)	0.0466 (5)
H2	0.0581	0.9147	0.1704	0.056*
C3	0.0737 (2)	0.7794 (2)	0.3487 (2)	0.0423 (5)
H3	−0.0130	0.8221	0.3865	0.051*
C4	0.1558 (2)	0.66235 (19)	0.42223 (18)	0.0322 (4)
C5	0.28421 (19)	0.59899 (18)	0.35979 (16)	0.0292 (4)
C6	0.1081 (2)	0.6047 (2)	0.55748 (18)	0.0351 (4)
H6	0.1154	0.5100	0.5905	0.042*
C7	0.0551 (2)	0.6840 (2)	0.63386 (18)	0.0351 (4)
H7	0.0687	0.7750	0.6017	0.042*
C8	−0.02223 (19)	0.64829 (19)	0.76227 (17)	0.0305 (4)
C9	−0.0772 (2)	0.5278 (2)	0.81369 (19)	0.0378 (4)
H9	−0.0499	0.4569	0.7739	0.045*
C10	−0.1717 (2)	0.5126 (2)	0.92315 (19)	0.0374 (4)
H10	−0.2075	0.4301	0.9564	0.045*
C11	−0.1559 (2)	0.7216 (2)	0.93976 (19)	0.0405 (4)
H11	−0.1811	0.7890	0.9838	0.049*
C12	−0.0591 (2)	0.7437 (2)	0.83136 (19)	0.0395 (4)
H12	−0.0182	0.8238	0.8044	0.047*
C13	0.61848 (18)	0.15824 (16)	0.25070 (15)	0.0236 (3)
C14	0.65612 (18)	0.12941 (17)	0.37782 (16)	0.0260 (3)
H14	0.6602	0.2015	0.4120	0.031*
C15	0.68768 (19)	−0.00338 (17)	0.45486 (16)	0.0275 (3)
C16	0.67891 (19)	−0.10810 (16)	0.40280 (17)	0.0272 (3)
H16	0.6998	−0.1987	0.4537	0.033*
C17	0.63983 (18)	−0.08176 (16)	0.27693 (16)	0.0251 (3)
C18	0.60952 (19)	0.05199 (16)	0.20019 (16)	0.0253 (3)
H18	0.5832	0.0704	0.1150	0.030*
C19	0.58834 (18)	0.30377 (16)	0.17058 (16)	0.0249 (3)
C20	0.62541 (19)	−0.19701 (17)	0.22521 (17)	0.0283 (4)
C21	0.7299 (2)	−0.0319 (2)	0.59072 (18)	0.0405 (4)
H21A	0.8344	−0.0259	0.5903	0.061*
H21B	0.7141	−0.1226	0.6392	0.061*
H21C	0.6684	0.0343	0.6305	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cd1	0.03605 (8)	0.01670 (6)	0.02152 (7)	−0.00628 (4)	0.00366 (5)	−0.00660 (5)
N1	0.0355 (8)	0.0292 (7)	0.0250 (7)	−0.0070 (6)	0.0046 (6)	−0.0078 (6)
N2	0.0383 (8)	0.0344 (8)	0.0272 (7)	−0.0081 (7)	0.0061 (6)	−0.0098 (7)
N3	0.0447 (9)	0.0355 (9)	0.0287 (8)	0.0013 (7)	0.0082 (7)	−0.0041 (7)
O1	0.0609 (9)	0.0158 (5)	0.0311 (7)	−0.0066 (5)	0.0002 (6)	−0.0076 (5)
O2	0.0543 (8)	0.0298 (7)	0.0252 (6)	−0.0072 (6)	−0.0068 (6)	−0.0021 (5)
O3	0.0576 (8)	0.0227 (6)	0.0290 (7)	−0.0113 (6)	−0.0002 (6)	−0.0104 (5)
O4	0.0586 (9)	0.0175 (6)	0.0405 (7)	−0.0049 (6)	−0.0067 (6)	−0.0087 (6)
C1	0.0466 (11)	0.0328 (10)	0.0301 (9)	−0.0024 (8)	0.0026 (8)	−0.0057 (8)
C2	0.0501 (12)	0.0403 (11)	0.0387 (11)	0.0089 (9)	−0.0032 (9)	−0.0059 (9)
C3	0.0369 (10)	0.0474 (12)	0.0399 (11)	0.0005 (9)	0.0052 (8)	−0.0162 (9)
C4	0.0296 (9)	0.0366 (10)	0.0325 (9)	−0.0085 (7)	0.0045 (7)	−0.0137 (8)
C5	0.0323 (9)	0.0318 (9)	0.0265 (8)	−0.0097 (7)	0.0023 (7)	−0.0117 (7)
C6	0.0328 (9)	0.0398 (10)	0.0324 (9)	−0.0085 (8)	0.0047 (7)	−0.0104 (8)
C7	0.0326 (9)	0.0381 (10)	0.0358 (10)	−0.0098 (8)	0.0058 (8)	−0.0124 (8)
C8	0.0270 (8)	0.0348 (9)	0.0295 (9)	−0.0069 (7)	0.0008 (7)	−0.0087 (8)
C9	0.0410 (10)	0.0385 (10)	0.0401 (10)	−0.0119 (8)	0.0079 (8)	−0.0214 (9)
C10	0.0424 (11)	0.0343 (10)	0.0388 (10)	−0.0142 (8)	0.0091 (8)	−0.0146 (8)
C11	0.0542 (12)	0.0361 (10)	0.0349 (10)	−0.0131 (9)	0.0099 (9)	−0.0170 (9)
C12	0.0509 (12)	0.0348 (10)	0.0354 (10)	−0.0151 (9)	0.0074 (9)	−0.0124 (8)
C13	0.0269 (8)	0.0188 (7)	0.0255 (8)	−0.0059 (6)	0.0020 (6)	−0.0071 (6)
C14	0.0305 (8)	0.0226 (8)	0.0276 (8)	−0.0059 (6)	−0.0004 (7)	−0.0108 (7)
C15	0.0281 (8)	0.0277 (8)	0.0253 (8)	−0.0043 (7)	−0.0022 (7)	−0.0053 (7)
C16	0.0305 (9)	0.0183 (7)	0.0300 (9)	−0.0032 (6)	−0.0012 (7)	−0.0032 (7)
C17	0.0289 (8)	0.0192 (7)	0.0284 (8)	−0.0057 (6)	0.0023 (6)	−0.0088 (7)
C18	0.0336 (9)	0.0204 (7)	0.0227 (8)	−0.0066 (6)	0.0026 (6)	−0.0074 (6)
C19	0.0273 (8)	0.0199 (7)	0.0259 (8)	−0.0051 (6)	0.0024 (6)	−0.0047 (7)
C20	0.0336 (9)	0.0205 (8)	0.0321 (9)	−0.0077 (7)	0.0061 (7)	−0.0105 (7)
C21	0.0469 (11)	0.0422 (11)	0.0310 (10)	−0.0033 (9)	−0.0114 (8)	−0.0074 (9)

Geometric parameters (Å, º)

Cd1—O1	2.1974 (14)	C4—C6	1.467 (3)
Cd1—O2^i	2.2959 (15)	C6—C7	1.324 (3)
Cd1—O3^ii	2.3021 (13)	C6—H6	0.9400
Cd1—N2^iii	2.3464 (16)	C7—C8	1.469 (3)
Cd1—N1	2.4133 (16)	C7—H7	0.9400
Cd1—O4^ii	2.4511 (14)	C8—C12	1.382 (3)
Cd1—C20^ii	2.7110 (18)	C8—C9	1.387 (3)
N1—C5	1.348 (2)	C9—C10	1.375 (3)
N1—C1	1.351 (2)	C9—H9	0.9400
N2—C11	1.331 (2)	C10—H10	0.9400
N2—C10	1.339 (2)	C11—C12	1.380 (3)
N2—Cd1^iv	2.3464 (16)	C11—H11	0.9400
N3—C5	1.340 (2)	C12—H12	0.9400
N3—H3A	0.8700	C13—C18	1.393 (2)
N3—H3B	0.8700	C13—C14	1.395 (2)
O1—C19	1.268 (2)	C13—C19	1.503 (2)
O2—C19	1.240 (2)	C14—C15	1.387 (2)
O2—Cd1^i	2.2959 (15)	C14—H14	0.9400
O3—C20	1.256 (2)	C15—C16	1.389 (2)
O3—Cd1^v	2.3021 (13)	C15—C21	1.500 (2)
O4—C20	1.257 (2)	C16—C17	1.390 (2)
O4—Cd1^v	2.4511 (14)	C16—H16	0.9400
C1—C2	1.365 (3)	C17—C18	1.393 (2)
C1—H1	0.9400	C17—C20	1.502 (2)
C2—C3	1.387 (3)	C18—H18	0.9400
C2—H2	0.9400	C20—Cd1^v	2.7110 (18)
C3—C4	1.377 (3)	C21—H21A	0.9700
C3—H3	0.9400	C21—H21B	0.9700
C4—C5	1.428 (2)	C21—H21C	0.9700
O1—Cd1—O2^i	113.38 (6)	C6—C7—C8	128.47 (18)
O1—Cd1—O3^ii	151.64 (5)	C6—C7—H7	115.8
O2^i—Cd1—O3^ii	93.88 (6)	C8—C7—H7	115.8
O1—Cd1—N2^iii	100.32 (6)	C12—C8—C9	116.58 (17)
O2^i—Cd1—N2^iii	87.33 (6)	C12—C8—C7	119.68 (17)
O3^ii—Cd1—N2^iii	88.10 (6)	C9—C8—C7	123.30 (17)
O1—Cd1—N1	90.89 (6)	C10—C9—C8	119.68 (18)
O2^i—Cd1—N1	84.47 (5)	C10—C9—H9	120.2
O3^ii—Cd1—N1	83.84 (6)	C8—C9—H9	120.2
N2^iii—Cd1—N1	168.07 (5)	N2—C10—C9	123.44 (18)
O1—Cd1—O4^ii	96.69 (5)	N2—C10—H10	118.3
O2^i—Cd1—O4^ii	147.58 (5)	C9—C10—H10	118.3
O3^ii—Cd1—O4^ii	55.07 (5)	N2—C11—C12	123.02 (18)
N2^iii—Cd1—O4^ii	99.38 (6)	N2—C11—H11	118.5
N1—Cd1—O4^ii	83.18 (5)	C12—C11—H11	118.5
O1—Cd1—C20^ii	124.16 (5)	C11—C12—C8	120.19 (18)
O2^i—Cd1—C20^ii	120.63 (5)	C11—C12—H12	119.9
O3^ii—Cd1—C20^ii	27.51 (5)	C8—C12—H12	119.9
N2^iii—Cd1—C20^ii	95.37 (6)	C18—C13—C14	119.59 (15)
N1—Cd1—C20^ii	81.47 (6)	C18—C13—C19	121.15 (15)
O4^ii—Cd1—C20^ii	27.61 (5)	C14—C13—C19	119.27 (14)
C5—N1—C1	118.71 (16)	C15—C14—C13	121.42 (15)
C5—N1—Cd1	128.47 (12)	C15—C14—H14	119.3
C1—N1—Cd1	111.45 (12)	C13—C14—H14	119.3
C11—N2—C10	116.83 (16)	C14—C15—C16	118.23 (15)
C11—N2—Cd1^iv	119.51 (13)	C14—C15—C21	120.44 (16)
C10—N2—Cd1^iv	121.47 (13)	C16—C15—C21	121.33 (16)
C5—N3—H3A	120.0	C15—C16—C17	121.36 (15)
C5—N3—H3B	120.0	C15—C16—H16	119.3
H3A—N3—H3B	120.0	C17—C16—H16	119.3
C19—O1—Cd1	121.91 (11)	C16—C17—C18	119.87 (15)
C19—O2—Cd1^i	156.89 (13)	C16—C17—C20	120.03 (15)
C20—O3—Cd1^v	94.68 (10)	C18—C17—C20	120.07 (15)
C20—O4—Cd1^v	87.78 (11)	C13—C18—C17	119.52 (15)
N1—C1—C2	123.83 (18)	C13—C18—H18	120.2
N1—C1—H1	118.1	C17—C18—H18	120.2
C2—C1—H1	118.1	O2—C19—O1	124.34 (15)
C1—C2—C3	117.28 (19)	O2—C19—C13	119.49 (15)
C1—C2—H2	121.4	O1—C19—C13	116.12 (14)
C3—C2—H2	121.4	O3—C20—O4	122.26 (16)
C4—C3—C2	121.76 (18)	O3—C20—C17	118.02 (15)
C4—C3—H3	119.1	O4—C20—C17	119.72 (16)
C2—C3—H3	119.1	O3—C20—Cd1^v	57.81 (9)
C3—C4—C5	117.10 (17)	O4—C20—Cd1^v	64.61 (9)
C3—C4—C6	120.45 (17)	C17—C20—Cd1^v	173.60 (12)
C5—C4—C6	122.41 (17)	C15—C21—H21A	109.5
N3—C5—N1	117.32 (16)	C15—C21—H21B	109.5
N3—C5—C4	121.50 (16)	H21A—C21—H21B	109.5
N1—C5—C4	121.18 (17)	C15—C21—H21C	109.5
C7—C6—C4	121.10 (18)	H21A—C21—H21C	109.5
C7—C6—H6	119.5	H21B—C21—H21C	109.5
C4—C6—H6	119.5

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.87	2.14	2.978 (2)	161
N3—H3B···O4^vi	0.87	2.23	3.082 (2)	165

Symmetry code: (vi) −x+1, −y, −z+1.

Poly[[µ-trans-1-(2-aminopyridin-3-yl)-2-(pyridin-4-yl)ethene-κ²N:N'](µ₂-5-hydroxyisophthalato-κ⁴O¹,O^1':O³:O⁵)cadmium(II)] (II)

Crystal data

[Cd(C8H4O5)(C12H11N3)]	Dx = 1.787 Mg m^−3
Mr = 489.76	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 64725 reflections
a = 12.387 (3) Å	θ = 3.3–27.6°
b = 14.684 (3) Å	µ = 1.24 mm^−1
c = 20.016 (4) Å	T = 223 K
V = 3640.7 (14) Å^3	Block, yellow
Z = 8	0.18 × 0.15 × 0.11 mm
F(000) = 1952

Data collection

Bruker SMART CCD area detector diffractometer	3775 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
phi and ω scans	θmax = 27.6°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→16
Tmin = 0.853, Tmax = 0.921	k = −19→18
64725 measured reflections	l = −25→25
4173 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.020	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.054	w = 1/[σ^2(Fo^2) + (0.0257P)^2 + 2.3943P] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max = 0.005
4173 reflections	Δρmax = 0.36 e Å^−3
266 parameters	Δρmin = −0.71 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cd1	0.48864 (2)	0.61822 (2)	0.87458 (2)	0.01753 (5)
N1	0.35402 (11)	0.50694 (10)	0.88858 (7)	0.0227 (3)
N2	−0.36006 (12)	0.53178 (11)	0.87845 (7)	0.0254 (3)
N3	0.22766 (13)	0.61335 (10)	0.91990 (9)	0.0329 (4)
H3A	0.2801	0.6517	0.9264	0.039*
H3B	0.1613	0.6300	0.9271	0.039*
O1	0.51172 (11)	0.63091 (11)	0.75542 (7)	0.0401 (4)
O2	0.37207 (11)	0.69117 (10)	0.80604 (6)	0.0317 (3)
O3	0.55494 (10)	0.71467 (10)	0.50613 (6)	0.0371 (3)
O4	0.43607 (11)	0.81688 (10)	0.47007 (6)	0.0379 (3)
O5	0.11421 (10)	0.75300 (9)	0.61704 (6)	0.0259 (3)
H5	0.1012 (19)	0.7673 (17)	0.5792 (13)	0.043 (7)*
C1	0.37896 (15)	0.42128 (13)	0.86961 (9)	0.0293 (4)
H1	0.4521	0.4063	0.8635	0.035*
C2	0.30317 (16)	0.35503 (14)	0.85877 (12)	0.0383 (5)
H2	0.3236	0.2961	0.8454	0.046*
C3	0.19511 (17)	0.37743 (13)	0.86804 (11)	0.0360 (5)
H3	0.1416	0.3331	0.8608	0.043*
C4	0.16542 (13)	0.46397 (12)	0.88767 (9)	0.0232 (3)
C5	0.24918 (13)	0.52835 (11)	0.89875 (8)	0.0204 (3)
C6	0.05153 (13)	0.48929 (12)	0.89679 (9)	0.0254 (3)
H6	0.0345	0.5323	0.9300	0.030*
C7	−0.02907 (14)	0.45450 (13)	0.86047 (10)	0.0272 (4)
H7	−0.0113	0.4118	0.8273	0.033*
C8	−0.14318 (13)	0.47824 (12)	0.86867 (9)	0.0241 (3)
C9	−0.18534 (14)	0.51351 (13)	0.92748 (9)	0.0295 (4)
H9	−0.1409	0.5202	0.9652	0.035*
C10	−0.29258 (14)	0.53881 (14)	0.93044 (9)	0.0308 (4)
H10	−0.3195	0.5621	0.9709	0.037*
C11	−0.32033 (14)	0.49593 (13)	0.82193 (10)	0.0301 (4)
H11	−0.3666	0.4899	0.7850	0.036*
C12	−0.21491 (14)	0.46754 (13)	0.81560 (10)	0.0315 (4)
H12	−0.1913	0.4409	0.7755	0.038*
C13	0.37814 (13)	0.70374 (11)	0.68835 (7)	0.0182 (3)
C14	0.26758 (13)	0.71911 (11)	0.68341 (7)	0.0199 (3)
H14	0.2228	0.7119	0.7210	0.024*
C15	0.22424 (13)	0.74512 (11)	0.62254 (7)	0.0194 (3)
C16	0.29080 (13)	0.76130 (12)	0.56827 (8)	0.0231 (3)
H16	0.2612	0.7828	0.5280	0.028*
C17	0.40141 (13)	0.74577 (11)	0.57307 (8)	0.0204 (3)
C18	0.44517 (13)	0.71487 (11)	0.63301 (7)	0.0191 (3)
H18	0.5192	0.7016	0.6361	0.023*
C19	0.42451 (13)	0.67335 (11)	0.75376 (8)	0.0206 (3)
C20	0.47056 (13)	0.76013 (13)	0.51226 (8)	0.0233 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cd1	0.01361 (7)	0.02614 (8)	0.01285 (7)	0.00256 (4)	−0.00130 (4)	−0.00154 (4)
N1	0.0147 (6)	0.0257 (7)	0.0278 (7)	0.0013 (5)	0.0010 (5)	−0.0010 (6)
N2	0.0167 (7)	0.0321 (8)	0.0273 (7)	0.0034 (6)	−0.0017 (5)	0.0028 (6)
N3	0.0156 (7)	0.0303 (8)	0.0529 (11)	−0.0029 (6)	0.0066 (7)	−0.0161 (7)
O1	0.0307 (7)	0.0701 (11)	0.0194 (7)	0.0227 (7)	−0.0040 (5)	0.0029 (7)
O2	0.0349 (7)	0.0466 (8)	0.0137 (5)	0.0142 (6)	−0.0001 (5)	0.0032 (5)
O3	0.0222 (6)	0.0615 (9)	0.0276 (7)	0.0154 (6)	0.0085 (5)	0.0186 (6)
O4	0.0265 (7)	0.0602 (9)	0.0270 (7)	0.0146 (6)	0.0100 (5)	0.0250 (6)
O5	0.0130 (6)	0.0417 (8)	0.0230 (6)	0.0012 (5)	−0.0005 (4)	0.0095 (5)
C1	0.0182 (8)	0.0273 (9)	0.0423 (11)	0.0064 (7)	0.0013 (7)	0.0005 (8)
C2	0.0267 (10)	0.0225 (9)	0.0657 (14)	0.0064 (8)	−0.0015 (9)	−0.0053 (9)
C3	0.0226 (10)	0.0237 (9)	0.0618 (14)	−0.0009 (7)	−0.0047 (9)	−0.0026 (8)
C4	0.0155 (7)	0.0241 (8)	0.0301 (9)	0.0010 (6)	−0.0023 (6)	0.0012 (7)
C5	0.0154 (7)	0.0250 (8)	0.0209 (7)	0.0018 (6)	0.0006 (6)	−0.0003 (6)
C6	0.0163 (8)	0.0251 (8)	0.0347 (9)	0.0002 (7)	0.0006 (7)	0.0022 (7)
C7	0.0173 (8)	0.0274 (9)	0.0368 (10)	0.0013 (7)	0.0005 (7)	−0.0009 (7)
C8	0.0152 (8)	0.0217 (8)	0.0352 (9)	−0.0011 (6)	−0.0018 (6)	0.0030 (7)
C9	0.0192 (8)	0.0434 (11)	0.0259 (9)	0.0023 (7)	−0.0043 (7)	0.0061 (8)
C10	0.0222 (8)	0.0468 (11)	0.0233 (9)	0.0068 (8)	0.0006 (7)	0.0047 (8)
C11	0.0204 (8)	0.0363 (10)	0.0337 (10)	0.0039 (7)	−0.0076 (7)	−0.0089 (8)
C12	0.0211 (8)	0.0378 (10)	0.0355 (10)	0.0043 (7)	−0.0021 (7)	−0.0124 (8)
C13	0.0188 (7)	0.0216 (7)	0.0142 (7)	0.0002 (6)	−0.0025 (6)	0.0012 (6)
C14	0.0181 (7)	0.0266 (8)	0.0151 (7)	−0.0006 (6)	0.0019 (6)	0.0010 (6)
C15	0.0131 (7)	0.0264 (8)	0.0186 (8)	0.0007 (6)	−0.0009 (5)	0.0022 (6)
C16	0.0173 (7)	0.0357 (9)	0.0164 (7)	0.0012 (7)	−0.0015 (6)	0.0080 (7)
C17	0.0173 (7)	0.0278 (8)	0.0160 (7)	0.0000 (6)	0.0008 (6)	0.0043 (6)
C18	0.0137 (7)	0.0253 (8)	0.0183 (7)	−0.0005 (6)	−0.0015 (5)	0.0020 (6)
C19	0.0211 (8)	0.0239 (7)	0.0168 (7)	−0.0016 (6)	−0.0044 (6)	0.0007 (6)
C20	0.0161 (7)	0.0369 (9)	0.0167 (8)	−0.0001 (7)	0.0005 (6)	0.0058 (7)

Geometric parameters (Å, º)

Cd1—O4^i	2.2329 (12)	C3—C4	1.380 (3)
Cd1—O2	2.2614 (12)	C3—H3	0.9400
Cd1—N2^ii	2.2649 (15)	C4—C5	1.421 (2)
Cd1—N1	2.3513 (15)	C4—C6	1.470 (2)
Cd1—O1	2.4094 (15)	C6—C7	1.337 (3)
Cd1—O5^iii	2.5229 (14)	C6—H6	0.9400
Cd1—C19	2.6709 (16)	C7—C8	1.465 (2)
N1—C1	1.350 (2)	C7—H7	0.9400
N1—C5	1.352 (2)	C8—C9	1.388 (3)
N2—C10	1.339 (2)	C8—C12	1.394 (2)
N2—C11	1.341 (2)	C9—C10	1.381 (2)
N2—Cd1^iv	2.2650 (15)	C9—H9	0.9400
N3—C5	1.345 (2)	C10—H10	0.9400
N3—H3A	0.8700	C11—C12	1.377 (2)
N3—H3B	0.8700	C11—H11	0.9400
O1—C19	1.248 (2)	C12—H12	0.9400
O2—C19	1.259 (2)	C13—C14	1.392 (2)
O3—C20	1.246 (2)	C13—C18	1.394 (2)
O4—C20	1.261 (2)	C13—C19	1.498 (2)
O4—Cd1^v	2.2330 (12)	C14—C15	1.385 (2)
O5—C15	1.3723 (19)	C14—H14	0.9400
O5—Cd1^vi	2.5229 (14)	C15—C16	1.384 (2)
O5—H5	0.80 (3)	C16—C17	1.392 (2)
C1—C2	1.369 (3)	C16—H16	0.9400
C1—H1	0.9400	C17—C18	1.392 (2)
C2—C3	1.391 (3)	C17—C20	1.503 (2)
C2—H2	0.9400	C18—H18	0.9400
O4^i—Cd1—O2	97.52 (5)	N1—C5—C4	121.56 (15)
O4^i—Cd1—N2^ii	116.82 (5)	C7—C6—C4	123.55 (18)
O2—Cd1—N2^ii	144.55 (5)	C7—C6—H6	118.2
O4^i—Cd1—N1	89.30 (5)	C4—C6—H6	118.2
O2—Cd1—N1	87.06 (5)	C6—C7—C8	124.67 (18)
N2^ii—Cd1—N1	101.15 (6)	C6—C7—H7	117.7
O4^i—Cd1—O1	148.10 (6)	C8—C7—H7	117.7
O2—Cd1—O1	55.85 (4)	C9—C8—C12	116.65 (16)
N2^ii—Cd1—O1	88.80 (5)	C9—C8—C7	123.15 (16)
N1—Cd1—O1	104.83 (5)	C12—C8—C7	120.19 (17)
O4^i—Cd1—O5^iii	77.76 (5)	C10—C9—C8	119.93 (17)
O2—Cd1—O5^iii	93.58 (5)	C10—C9—H9	120.0
N2^ii—Cd1—O5^iii	85.82 (5)	C8—C9—H9	120.0
N1—Cd1—O5^iii	167.02 (5)	N2—C10—C9	123.13 (18)
O1—Cd1—O5^iii	86.10 (5)	N2—C10—H10	118.4
O4^i—Cd1—C19	123.98 (6)	C9—C10—H10	118.4
O2—Cd1—C19	28.04 (5)	N2—C11—C12	123.00 (17)
N2^ii—Cd1—C19	116.55 (5)	N2—C11—H11	118.5
N1—Cd1—C19	96.18 (5)	C12—C11—H11	118.5
O1—Cd1—C19	27.83 (5)	C11—C12—C8	120.03 (17)
O5^iii—Cd1—C19	90.33 (5)	C11—C12—H12	120.0
C1—N1—C5	118.62 (15)	C8—C12—H12	120.0
C1—N1—Cd1	116.86 (11)	C14—C13—C18	120.72 (14)
C5—N1—Cd1	122.53 (11)	C14—C13—C19	119.20 (14)
C10—N2—C11	117.18 (15)	C18—C13—C19	120.07 (14)
C10—N2—Cd1^iv	120.00 (12)	C15—C14—C13	119.25 (14)
C11—N2—Cd1^iv	119.65 (11)	C15—C14—H14	120.4
C5—N3—H3A	120.0	C13—C14—H14	120.4
C5—N3—H3B	120.0	O5—C15—C16	120.94 (14)
H3A—N3—H3B	120.0	O5—C15—C14	118.60 (14)
C19—O1—Cd1	87.83 (10)	C16—C15—C14	120.45 (15)
C19—O2—Cd1	94.38 (10)	C15—C16—C17	120.25 (15)
C20—O4—Cd1^v	139.16 (11)	C15—C16—H16	119.9
C15—O5—Cd1^vi	122.75 (11)	C17—C16—H16	119.9
C15—O5—H5	107.3 (17)	C16—C17—C18	119.73 (14)
Cd1^vi—O5—H5	98.3 (17)	C16—C17—C20	118.81 (14)
N1—C1—C2	123.35 (17)	C18—C17—C20	121.43 (14)
N1—C1—H1	118.3	C17—C18—C13	119.40 (15)
C2—C1—H1	118.3	C17—C18—H18	120.3
C1—C2—C3	118.09 (18)	C13—C18—H18	120.3
C1—C2—H2	121.0	O1—C19—O2	121.90 (15)
C3—C2—H2	121.0	O1—C19—C13	120.27 (15)
C4—C3—C2	120.81 (18)	O2—C19—C13	117.82 (14)
C4—C3—H3	119.6	O1—C19—Cd1	64.35 (9)
C2—C3—H3	119.6	O2—C19—Cd1	57.59 (8)
C3—C4—C5	117.55 (16)	C13—C19—Cd1	174.74 (11)
C3—C4—C6	121.59 (16)	O3—C20—O4	124.91 (15)
C5—C4—C6	120.86 (15)	O3—C20—C17	118.85 (15)
N3—C5—N1	116.98 (15)	O4—C20—C17	116.22 (14)
N3—C5—C4	121.46 (15)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x+1, y, z; (iii) x+1/2, y, −z+3/2; (iv) x−1, y, z; (v) x, −y+3/2, z−1/2; (vi) x−1/2, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O4^i	0.87	2.17	2.954 (2)	150
N3—H3B···O3^vi	0.87	2.25	2.997 (2)	144
O5—H5···O3^vii	0.80 (3)	1.82 (3)	2.6159 (18)	171 (2)

Symmetry codes: (i) x, −y+3/2, z+1/2; (vi) x−1/2, y, −z+3/2; (vii) x−1/2, −y+3/2, −z+1.