Synthesis, structure, thermostability and luminescence properties of Zn^II and Cd^II coordination polymers based on dimethysuccinate and flexible 1,4-bis­(imidazol-1-ylmeth­yl)benzene ligands

The design and synthesis of functional coordination polymers is motivated not only by their structural beauty but also by their potential applications. Zn^II and Cd^II coordination polymers are promising candidates for producing photoactive materials because these d¹⁰ metal ions not only possess a variety of coordination numbers and geometries, but also exhibit luminescence properties when bound to functional ligands. It is difficult to predict the final structure of such polymers because the assembly process is influenced by many subtle factors. Bis(imidazol-1-yl)-substituted alkane/benzene mol­ecules are good bridging ligands because their flexibility allows them to bend and rotate when they coordinate to metal centres. Two new Zn^II and Cd^II coordination polymers based on mixed ligands, namely, poly[[μ₂-1,4-bis­(imidazol-1-ylmeth­yl)benzene-κ²N³:N^3′]bis­(μ₃-2,2-di­methyl­butano­ato-κ³O¹:O⁴:O^4′)dizinc(II)], [Zn₂(C₆H₈O₄)₂(C₁₄H₁₄N₄)]_n, and poly[[μ₂-1,4-bis­(imidazol-1-ylmeth­yl)benzene-κ²N³:N^3′]bis­(μ₃-2,2-di­methyl­butano­ato-κ⁵O¹,O^1′:O⁴,O^4′:O⁴)dicadmium(II)], [Cd₂(C₆H₈O₄)₂(C₁₄H₁₄N₄)]_n, have been synthesized under hydro­thermal conditions and characterized by single-crystal X-ray diffraction, elemental analysis, IR spec­troscopy and thermogravimetric analysis. Both complexes crystallize in the monoclinic space group C2/c with similar unit-cell parameters and feature two-dimensional structures formed by the inter­connection of S-shaped Zn(Cd)–2,2-di­methyl­succinate chains with 1,4-bis­(imidazol-1-ylmeth­yl)benzene bridges. However, the Cd^II and Zn^II centres have different coordination numbers and the 2,2-di­methyl­succinate ligands display different coordination modes. Both complexes exhibit a blue photoluminescence in the solid state at room tem­perature.

Computing details

For both compounds, data collection: APEX2 (Bruker, 2012); cell refinement: APEX2 (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

(dj3530) Poly[[µ₂-1,4-bis(imidazol-1-ylmethyl)benzene-κ²N³:N^3']bis(µ₃-2,2-dimethylbutanoato-κ³O¹:O⁴:O^4')dizinc(II)]

Crystal data

[Zn2(C6H8O4)2(C14H14N4)]	F(000) = 1352
Mr = 657.28	Dx = 1.646 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.059 (6) Å	Cell parameters from 3260 reflections
b = 20.839 (13) Å	θ = 2.3–28.0°
c = 13.198 (8) Å	µ = 1.87 mm^−1
β = 106.567 (9)°	T = 296 K
V = 2652 (3) Å^3	Block, colorless
Z = 4	0.26 × 0.25 × 0.21 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	3263 independent reflections
Radiation source: fine-focus sealed tube	2617 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
phi and ω scans	θmax = 28.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −13→12
Tmin = 0.643, Tmax = 0.695	k = −20→27
8289 measured reflections	l = −17→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0561P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
3263 reflections	Δρmax = 0.88 e Å^−3
182 parameters	Δρmin = −0.70 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0216 (8)

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
C1	0.2417 (2)	0.89105 (12)	0.72458 (18)	0.0265 (5)
C2	0.1554 (2)	0.88417 (12)	0.60894 (17)	0.0257 (5)
C3	0.1814 (3)	0.93929 (11)	0.54097 (19)	0.0271 (5)
H3A	0.1194	0.9339	0.4703	0.033*
H3B	0.1553	0.9789	0.5689	0.033*
C4	0.3263 (3)	0.94752 (11)	0.53172 (18)	0.0256 (5)
C5	0.1838 (4)	0.81974 (13)	0.5637 (2)	0.0466 (8)
H5A	0.1290	0.8164	0.4913	0.070*
H5B	0.1600	0.7855	0.6038	0.070*
H5C	0.2804	0.8169	0.5675	0.070*
C6	0.0026 (3)	0.88723 (18)	0.6077 (2)	0.0508 (8)
H6A	−0.0553	0.8831	0.5363	0.076*
H6B	−0.0154	0.9276	0.6362	0.076*
H6C	−0.0170	0.8529	0.6498	0.076*
C7	0.3469 (2)	0.90206 (12)	1.11939 (18)	0.0260 (5)
H7	0.3438	0.9450	1.1375	0.031*
C8	0.3431 (3)	0.79762 (12)	1.1277 (2)	0.0337 (6)
H8	0.3367	0.7559	1.1507	0.040*
C9	0.3647 (3)	0.81574 (12)	1.0352 (2)	0.0333 (6)
H9	0.3767	0.7880	0.9833	0.040*
C10	0.2962 (2)	0.85880 (13)	1.28073 (19)	0.0307 (5)
H10A	0.3337	0.8987	1.3150	0.037*
H10B	0.3387	0.8238	1.3272	0.037*
C11	0.1424 (2)	0.85765 (12)	1.26456 (17)	0.0255 (5)
C12	0.0702 (2)	0.80013 (12)	1.25671 (19)	0.0302 (5)
H12	0.1173	0.7614	1.2606	0.036*
C13	0.0704 (3)	0.91564 (12)	1.25725 (19)	0.0285 (5)
H13	0.1180	0.9543	1.2622	0.034*
Zn1	0.38320 (3)	0.933764 (12)	0.906393 (19)	0.02351 (13)
O1	0.2788 (2)	0.84343 (9)	0.78101 (15)	0.0447 (5)
O2	0.26604 (19)	0.94784 (9)	0.76064 (14)	0.0347 (4)
O3	0.42509 (19)	0.92307 (9)	0.60092 (15)	0.0367 (5)
O4	0.3406 (2)	0.97935 (9)	0.45507 (14)	0.0414 (5)
N1	0.36634 (19)	0.88157 (9)	1.03007 (15)	0.0265 (4)
N2	0.33239 (19)	0.85287 (9)	1.18050 (15)	0.0249 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0207 (12)	0.0412 (14)	0.0194 (11)	0.0023 (10)	0.0085 (9)	−0.0014 (10)
C2	0.0218 (12)	0.0342 (13)	0.0194 (11)	−0.0070 (9)	0.0033 (9)	0.0001 (9)
C3	0.0225 (12)	0.0360 (13)	0.0207 (11)	0.0015 (10)	0.0028 (9)	0.0052 (9)
C4	0.0279 (13)	0.0283 (12)	0.0220 (11)	−0.0078 (9)	0.0093 (9)	−0.0030 (9)
C5	0.070 (2)	0.0335 (14)	0.0351 (15)	−0.0112 (14)	0.0129 (14)	−0.0075 (11)
C6	0.0230 (14)	0.089 (2)	0.0386 (16)	−0.0137 (14)	0.0051 (12)	0.0072 (15)
C7	0.0226 (12)	0.0299 (12)	0.0262 (12)	0.0015 (9)	0.0081 (9)	0.0020 (9)
C8	0.0351 (14)	0.0292 (13)	0.0363 (14)	−0.0030 (11)	0.0093 (11)	0.0004 (10)
C9	0.0347 (14)	0.0346 (14)	0.0308 (13)	−0.0031 (11)	0.0095 (11)	−0.0063 (10)
C10	0.0219 (12)	0.0472 (15)	0.0222 (12)	−0.0009 (11)	0.0052 (9)	0.0033 (10)
C11	0.0224 (12)	0.0377 (13)	0.0172 (10)	−0.0001 (10)	0.0066 (9)	0.0019 (9)
C12	0.0274 (13)	0.0308 (13)	0.0341 (13)	0.0049 (10)	0.0113 (10)	0.0023 (10)
C13	0.0306 (13)	0.0295 (12)	0.0244 (12)	−0.0049 (10)	0.0060 (10)	−0.0001 (9)
Zn1	0.01921 (18)	0.0334 (2)	0.01853 (17)	0.00077 (10)	0.00643 (11)	−0.00087 (10)
O1	0.0543 (13)	0.0521 (12)	0.0265 (10)	0.0087 (10)	0.0095 (9)	0.0137 (8)
O2	0.0324 (10)	0.0427 (10)	0.0240 (9)	0.0072 (8)	0.0002 (7)	−0.0090 (7)
O3	0.0198 (9)	0.0593 (12)	0.0326 (10)	0.0003 (8)	0.0098 (8)	0.0108 (8)
O4	0.0548 (12)	0.0417 (11)	0.0305 (10)	−0.0182 (9)	0.0163 (9)	0.0060 (8)
N1	0.0199 (10)	0.0356 (11)	0.0239 (10)	−0.0011 (8)	0.0061 (8)	0.0004 (8)
N2	0.0183 (10)	0.0339 (11)	0.0233 (10)	−0.0017 (8)	0.0071 (8)	0.0034 (8)

Geometric parameters (Å, º)

C1—O1	1.233 (3)	C8—C9	1.353 (4)
C1—O2	1.273 (3)	C8—N2	1.366 (3)
C1—C2	1.532 (3)	C8—H8	0.9300
C1—Zn1	2.575 (3)	C9—N1	1.374 (3)
C2—C3	1.525 (3)	C9—H9	0.9300
C2—C5	1.529 (4)	C10—N2	1.474 (3)
C2—C6	1.533 (4)	C10—C11	1.501 (3)
C3—C4	1.506 (4)	C10—H10A	0.9700
C3—H3A	0.9700	C10—H10B	0.9700
C3—H3B	0.9700	C11—C12	1.390 (4)
C4—O3	1.251 (3)	C11—C13	1.398 (4)
C4—O4	1.252 (3)	C12—C12^i	1.372 (5)
C5—H5A	0.9600	C12—H12	0.9300
C5—H5B	0.9600	C13—C13^i	1.374 (5)
C5—H5C	0.9600	C13—H13	0.9300
C6—H6A	0.9600	Zn1—O2	1.970 (2)
C6—H6B	0.9600	Zn1—O3^ii	1.971 (2)
C6—H6C	0.9600	Zn1—O4^iii	2.008 (2)
C7—N1	1.320 (3)	Zn1—N1	2.008 (2)
C7—N2	1.338 (3)	O3—Zn1^ii	1.971 (2)
C7—H7	0.9300	O4—Zn1^iv	2.008 (2)
O1—C1—O2	122.0 (2)	N2—C8—H8	126.8
O1—C1—C2	121.0 (2)	C8—C9—N1	109.3 (2)
O2—C1—C2	117.0 (2)	C8—C9—H9	125.3
O1—C1—Zn1	73.95 (15)	N1—C9—H9	125.3
O2—C1—Zn1	48.22 (11)	N2—C10—C11	112.30 (19)
C2—C1—Zn1	165.08 (17)	N2—C10—H10A	109.1
C3—C2—C5	110.4 (2)	C11—C10—H10A	109.1
C3—C2—C1	111.84 (19)	N2—C10—H10B	109.1
C5—C2—C1	110.8 (2)	C11—C10—H10B	109.1
C3—C2—C6	107.6 (2)	H10A—C10—H10B	107.9
C5—C2—C6	109.3 (2)	C12—C11—C13	119.4 (2)
C1—C2—C6	106.7 (2)	C12—C11—C10	121.3 (2)
C4—C3—C2	117.75 (19)	C13—C11—C10	119.3 (2)
C4—C3—H3A	107.9	C12^i—C12—C11	120.42 (14)
C2—C3—H3A	107.9	C12^i—C12—H12	119.8
C4—C3—H3B	107.9	C11—C12—H12	119.8
C2—C3—H3B	107.9	C13^i—C13—C11	120.18 (14)
H3A—C3—H3B	107.2	C13^i—C13—H13	119.9
O3—C4—O4	123.7 (2)	C11—C13—H13	119.9
O3—C4—C3	118.7 (2)	O2—Zn1—O3^ii	106.87 (9)
O4—C4—C3	117.6 (2)	O2—Zn1—O4^iii	93.18 (8)
C2—C5—H5A	109.5	O3^ii—Zn1—O4^iii	114.74 (8)
C2—C5—H5B	109.5	O2—Zn1—N1	135.11 (9)
H5A—C5—H5B	109.5	O3^ii—Zn1—N1	106.80 (8)
C2—C5—H5C	109.5	O4^iii—Zn1—N1	98.81 (9)
H5A—C5—H5C	109.5	O2—Zn1—C1	28.81 (8)
H5B—C5—H5C	109.5	O3^ii—Zn1—C1	101.78 (8)
C2—C6—H6A	109.5	O4^iii—Zn1—C1	119.89 (8)
C2—C6—H6B	109.5	N1—Zn1—C1	114.70 (9)
H6A—C6—H6B	109.5	C1—O2—Zn1	102.97 (15)
C2—C6—H6C	109.5	C4—O3—Zn1^ii	120.23 (16)
H6A—C6—H6C	109.5	C4—O4—Zn1^iv	145.14 (17)
H6B—C6—H6C	109.5	C7—N1—C9	105.8 (2)
N1—C7—N2	111.1 (2)	C7—N1—Zn1	128.25 (17)
N1—C7—H7	124.4	C9—N1—Zn1	125.87 (17)
N2—C7—H7	124.4	C7—N2—C8	107.5 (2)
C9—C8—N2	106.3 (2)	C7—N2—C10	125.0 (2)
C9—C8—H8	126.8	C8—N2—C10	127.2 (2)
O1—C1—C2—C3	−151.1 (2)	O2—C1—Zn1—N1	141.44 (16)
O2—C1—C2—C3	32.7 (3)	C2—C1—Zn1—N1	148.8 (6)
Zn1—C1—C2—C3	26.6 (7)	O1—C1—O2—Zn1	6.0 (3)
O1—C1—C2—C5	−27.4 (3)	C2—C1—O2—Zn1	−177.87 (17)
O2—C1—C2—C5	156.4 (2)	O3^ii—Zn1—O2—C1	83.74 (16)
Zn1—C1—C2—C5	150.2 (6)	O4^iii—Zn1—O2—C1	−159.21 (16)
O1—C1—C2—C6	91.5 (3)	N1—Zn1—O2—C1	−53.4 (2)
O2—C1—C2—C6	−84.6 (3)	O4—C4—O3—Zn1^ii	0.2 (3)
Zn1—C1—C2—C6	−90.8 (6)	C3—C4—O3—Zn1^ii	−178.96 (16)
C5—C2—C3—C4	−62.2 (3)	O3—C4—O4—Zn1^iv	−83.7 (4)
C1—C2—C3—C4	61.7 (3)	C3—C4—O4—Zn1^iv	95.4 (3)
C6—C2—C3—C4	178.6 (2)	N2—C7—N1—C9	−0.3 (3)
C2—C3—C4—O3	−20.7 (3)	N2—C7—N1—Zn1	176.15 (15)
C2—C3—C4—O4	160.0 (2)	C8—C9—N1—C7	0.5 (3)
N2—C8—C9—N1	−0.5 (3)	C8—C9—N1—Zn1	−176.07 (17)
N2—C10—C11—C12	84.2 (3)	O2—Zn1—N1—C7	−109.6 (2)
N2—C10—C11—C13	−95.7 (3)	O3^ii—Zn1—N1—C7	113.3 (2)
C13—C11—C12—C12^i	−0.8 (4)	O4^iii—Zn1—N1—C7	−6.0 (2)
C10—C11—C12—C12^i	179.2 (3)	C1—Zn1—N1—C7	−134.76 (19)
C12—C11—C13—C13^i	0.2 (4)	O2—Zn1—N1—C9	66.3 (2)
C10—C11—C13—C13^i	−179.8 (3)	O3^ii—Zn1—N1—C9	−70.9 (2)
O1—C1—Zn1—O2	−174.7 (2)	O4^iii—Zn1—N1—C9	169.9 (2)
C2—C1—Zn1—O2	7.4 (6)	C1—Zn1—N1—C9	41.1 (2)
O1—C1—Zn1—O3^ii	81.61 (16)	N1—C7—N2—C8	0.0 (3)
O2—C1—Zn1—O3^ii	−103.66 (16)	N1—C7—N2—C10	−173.93 (19)
C2—C1—Zn1—O3^ii	−96.3 (6)	C9—C8—N2—C7	0.3 (3)
O1—C1—Zn1—O4^iii	−150.59 (14)	C9—C8—N2—C10	174.1 (2)
O2—C1—Zn1—O4^iii	24.13 (18)	C11—C10—N2—C7	89.6 (3)
C2—C1—Zn1—O4^iii	31.5 (7)	C11—C10—N2—C8	−83.2 (3)
O1—C1—Zn1—N1	−33.28 (17)

Symmetry codes: (i) −x, y, −z+5/2; (ii) −x+1, y, −z+3/2; (iii) x, −y+2, z+1/2; (iv) x, −y+2, z−1/2.

(dj3531) Poly[[µ₂-1,4-bis(imidazol-1-ylmethyl)benzene-κ²N³:N^3']bis(µ₃-2,2-dimethylbutanoato-κ³O¹:O⁴:O^4')dicadmium(II)]

Crystal data

[Cd2(C6H8O4)2(C14H14N4)]	F(000) = 1496
Mr = 751.34	Dx = 1.835 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.575 (3) Å	Cell parameters from 4764 reflections
b = 20.477 (5) Å	θ = 2.4–28.6°
c = 13.938 (3) Å	µ = 1.62 mm^−1
β = 115.703 (14)°	T = 296 K
V = 2719.6 (12) Å^3	Block, colorless
Z = 4	0.26 × 0.21 × 0.17 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	3381 independent reflections
Radiation source: fine-focus sealed tube	2963 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
phi and ω scans	θmax = 28.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −13→14
Tmin = 0.678, Tmax = 0.770	k = −27→26
8603 measured reflections	l = −18→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.092	w = 1/[σ^2(Fo^2) + (0.0533P)^2 + 0.0557P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.012
3381 reflections	Δρmax = 1.05 e Å^−3
184 parameters	Δρmin = −1.36 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0034 (2)

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
Cd1	0.773049 (19)	0.177121 (9)	0.923802 (13)	0.02770 (11)
O1	0.7807 (2)	0.10343 (10)	0.79074 (15)	0.0394 (5)
O2	0.7278 (2)	0.20682 (9)	0.75732 (15)	0.0372 (5)
O3	0.5599 (2)	0.13698 (13)	0.9058 (2)	0.0559 (6)
O4	0.6247 (2)	0.22514 (11)	0.9983 (2)	0.0575 (7)
N1	0.9369 (2)	0.12452 (11)	1.05943 (17)	0.0299 (5)
N2	1.1256 (2)	0.09868 (10)	1.20142 (16)	0.0269 (4)
C1	0.7430 (3)	0.14979 (13)	0.72774 (19)	0.0261 (5)
C2	0.7199 (3)	0.14116 (13)	0.6126 (2)	0.0288 (5)
C3	0.6051 (3)	0.18709 (13)	0.5407 (2)	0.0305 (6)
H3A	0.6391	0.2315	0.5579	0.037*
H3B	0.5886	0.1789	0.4677	0.037*
C4	0.5334 (3)	0.18223 (13)	0.9529 (2)	0.0317 (6)
C5	0.6856 (4)	0.07069 (15)	0.5756 (2)	0.0462 (8)
H5A	0.7557	0.0423	0.6253	0.069*
H5B	0.6843	0.0659	0.5066	0.069*
H5C	0.5953	0.0594	0.5715	0.069*
C6	0.8570 (4)	0.1594 (2)	0.6071 (3)	0.0487 (8)
H6A	0.8828	0.2033	0.6326	0.073*
H6B	0.8442	0.1566	0.5347	0.073*
H6C	0.9299	0.1299	0.6506	0.073*
C7	1.0450 (3)	0.14716 (13)	1.1438 (2)	0.0292 (5)
H7	1.0624	0.1912	1.1608	0.035*
C8	1.0673 (3)	0.04124 (13)	1.1521 (2)	0.0353 (6)
H8	1.1007	−0.0007	1.1742	0.042*
C9	0.9504 (3)	0.05839 (14)	1.0643 (2)	0.0362 (6)
H9	0.8888	0.0293	1.0148	0.043*
C10	1.2580 (3)	0.10580 (16)	1.2965 (2)	0.0342 (6)
H10A	1.2668	0.0707	1.3456	0.041*
H10B	1.2572	0.1467	1.3313	0.041*
C11	1.3831 (3)	0.10469 (13)	1.27156 (19)	0.0286 (5)
C12	1.4418 (3)	0.04608 (13)	1.2605 (2)	0.0354 (6)
H12	1.4020	0.0067	1.2668	0.042*
C13	1.4413 (3)	0.16262 (14)	1.2602 (2)	0.0320 (6)
H13	1.4027	0.2021	1.2676	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cd1	0.02447 (15)	0.03472 (15)	0.01904 (14)	−0.00038 (6)	0.00488 (10)	0.00079 (6)
O1	0.0466 (12)	0.0422 (11)	0.0241 (9)	0.0139 (9)	0.0105 (9)	0.0099 (8)
O2	0.0530 (13)	0.0323 (10)	0.0244 (9)	−0.0021 (9)	0.0149 (9)	−0.0015 (8)
O3	0.0362 (12)	0.0746 (16)	0.0618 (15)	−0.0112 (11)	0.0259 (11)	−0.0277 (13)
O4	0.0390 (13)	0.0442 (12)	0.0766 (17)	−0.0176 (10)	0.0133 (12)	−0.0101 (12)
N1	0.0260 (11)	0.0362 (11)	0.0240 (10)	0.0039 (9)	0.0076 (9)	0.0001 (9)
N2	0.0222 (10)	0.0359 (11)	0.0202 (10)	0.0022 (9)	0.0070 (8)	0.0014 (8)
C1	0.0195 (12)	0.0343 (13)	0.0206 (11)	0.0011 (10)	0.0049 (9)	0.0023 (10)
C2	0.0300 (14)	0.0364 (13)	0.0208 (12)	0.0042 (10)	0.0117 (10)	0.0036 (10)
C3	0.0326 (15)	0.0365 (13)	0.0202 (13)	0.0047 (11)	0.0096 (11)	0.0065 (10)
C4	0.0270 (14)	0.0385 (15)	0.0214 (13)	−0.0050 (10)	0.0028 (11)	0.0060 (10)
C5	0.064 (2)	0.0387 (16)	0.0335 (16)	0.0079 (15)	0.0191 (14)	−0.0023 (12)
C6	0.0310 (16)	0.080 (2)	0.0383 (18)	0.0061 (17)	0.0183 (14)	0.0065 (17)
C7	0.0275 (13)	0.0337 (13)	0.0237 (12)	0.0012 (10)	0.0085 (10)	0.0019 (10)
C8	0.0363 (15)	0.0306 (13)	0.0330 (14)	0.0019 (11)	0.0094 (12)	−0.0005 (11)
C9	0.0360 (15)	0.0360 (13)	0.0314 (14)	0.0000 (12)	0.0099 (12)	−0.0037 (11)
C10	0.0262 (13)	0.0524 (16)	0.0205 (12)	0.0020 (12)	0.0069 (10)	0.0009 (11)
C11	0.0237 (12)	0.0402 (14)	0.0166 (11)	0.0022 (10)	0.0039 (9)	0.0022 (10)
C12	0.0343 (15)	0.0328 (13)	0.0399 (15)	−0.0034 (11)	0.0169 (12)	0.0003 (11)
C13	0.0362 (16)	0.0332 (12)	0.0241 (13)	0.0021 (11)	0.0108 (11)	−0.0021 (10)

Geometric parameters (Å, º)

Cd1—N1	2.212 (2)	C3—H3A	0.9700
Cd1—O2	2.2406 (19)	C3—H3B	0.9700
Cd1—O3	2.309 (2)	C4—C3^ii	1.508 (4)
Cd1—O4^i	2.310 (2)	C5—H5A	0.9600
Cd1—O1	2.419 (2)	C5—H5B	0.9600
Cd1—O4	2.433 (3)	C5—H5C	0.9600
Cd1—C1	2.670 (3)	C6—H6A	0.9600
Cd1—C4	2.737 (3)	C6—H6B	0.9600
O1—C1	1.236 (3)	C6—H6C	0.9600
O2—C1	1.272 (3)	C7—H7	0.9300
O3—C4	1.236 (4)	C8—C9	1.355 (4)
O4—C4	1.255 (3)	C8—H8	0.9300
O4—Cd1^i	2.310 (2)	C9—H9	0.9300
N1—C7	1.319 (3)	C10—C11	1.506 (4)
N1—C9	1.360 (4)	C10—H10A	0.9700
N2—C7	1.328 (3)	C10—H10B	0.9700
N2—C8	1.367 (3)	C11—C13	1.377 (4)
N2—C10	1.459 (3)	C11—C12	1.390 (4)
C1—C2	1.525 (3)	C12—C12^iii	1.384 (6)
C2—C5	1.522 (4)	C12—H12	0.9304
C2—C3	1.519 (4)	C13—C13^iii	1.388 (6)
C2—C6	1.531 (4)	C13—H13	0.9306
C3—C4^ii	1.508 (4)
N1—Cd1—O2	138.88 (8)	C1—C2—C6	107.5 (2)
N1—Cd1—O3	106.58 (9)	C3—C2—C6	108.6 (2)
O2—Cd1—O3	102.97 (9)	C4^ii—C3—C2	116.1 (2)
N1—Cd1—O4^i	89.25 (9)	C4^ii—C3—H3A	108.3
O2—Cd1—O4^i	95.60 (9)	C2—C3—H3A	108.3
O3—Cd1—O4^i	126.55 (9)	C4^ii—C3—H3B	108.3
N1—Cd1—O1	94.43 (7)	C2—C3—H3B	108.3
O2—Cd1—O1	55.84 (7)	H3A—C3—H3B	107.4
O3—Cd1—O1	92.89 (8)	O3—C4—O4	119.4 (3)
O4^i—Cd1—O1	137.42 (9)	O3—C4—C3^ii	122.0 (2)
N1—Cd1—O4	104.06 (9)	O4—C4—C3^ii	118.6 (3)
O2—Cd1—O4	116.41 (8)	O3—C4—Cd1	56.96 (16)
O3—Cd1—O4	53.87 (8)	O4—C4—Cd1	62.74 (18)
O4^i—Cd1—O4	72.91 (9)	C3^ii—C4—Cd1	175.12 (19)
O1—Cd1—O4	145.23 (8)	C2—C5—H5A	109.5
N1—Cd1—C1	118.30 (8)	C2—C5—H5B	109.5
O2—Cd1—C1	28.33 (8)	H5A—C5—H5B	109.5
O3—Cd1—C1	97.88 (8)	C2—C5—H5C	109.5
O4^i—Cd1—C1	119.10 (9)	H5A—C5—H5C	109.5
O1—Cd1—C1	27.55 (7)	H5B—C5—H5C	109.5
O4—Cd1—C1	135.16 (8)	C2—C6—H6A	109.5
N1—Cd1—C4	108.93 (8)	C2—C6—H6B	109.5
O2—Cd1—C4	110.33 (8)	H6A—C6—H6B	109.5
O3—Cd1—C4	26.66 (8)	C2—C6—H6C	109.5
O4^i—Cd1—C4	99.91 (9)	H6A—C6—H6C	109.5
O1—Cd1—C4	118.58 (8)	H6B—C6—H6C	109.5
O4—Cd1—C4	27.30 (8)	N1—C7—N2	110.9 (2)
C1—Cd1—C4	116.91 (8)	N1—C7—H7	124.5
C1—O1—Cd1	87.57 (16)	N2—C7—H7	124.5
C1—O2—Cd1	94.95 (15)	C9—C8—N2	105.5 (2)
C4—O3—Cd1	96.38 (18)	C9—C8—H8	127.3
C4—O4—Cd1^i	160.8 (2)	N2—C8—H8	127.3
C4—O4—Cd1	90.0 (2)	C8—C9—N1	109.8 (2)
Cd1^i—O4—Cd1	107.09 (9)	C8—C9—H9	125.1
C7—N1—C9	105.9 (2)	N1—C9—H9	125.1
C7—N1—Cd1	130.22 (18)	N2—C10—C11	112.5 (2)
C9—N1—Cd1	123.63 (18)	N2—C10—H10A	109.1
C7—N2—C8	108.0 (2)	C11—C10—H10A	109.1
C7—N2—C10	125.9 (2)	N2—C10—H10B	109.1
C8—N2—C10	126.0 (2)	C11—C10—H10B	109.1
O1—C1—O2	121.5 (2)	H10A—C10—H10B	107.8
O1—C1—C2	120.9 (2)	C13—C11—C12	119.2 (3)
O2—C1—C2	117.6 (2)	C13—C11—C10	119.6 (2)
O1—C1—Cd1	64.88 (14)	C12—C11—C10	121.1 (2)
O2—C1—Cd1	56.73 (12)	C12^iii—C12—C11	120.28 (16)
C2—C1—Cd1	174.20 (18)	C12^iii—C12—H12	120.0
C5—C2—C1	111.9 (2)	C11—C12—H12	119.7
C5—C2—C3	111.0 (2)	C11—C13—C13^iii	120.50 (16)
C1—C2—C3	109.8 (2)	C11—C13—H13	119.7
C5—C2—C6	107.8 (3)	C13^iii—C13—H13	119.8
N1—Cd1—O1—C1	−151.59 (16)	O2—Cd1—C1—C2	−9.7 (17)
O2—Cd1—O1—C1	−2.20 (15)	O3—Cd1—C1—C2	93.1 (18)
O3—Cd1—O1—C1	101.53 (17)	O4^i—Cd1—C1—C2	−46.8 (18)
O4^i—Cd1—O1—C1	−57.9 (2)	O1—Cd1—C1—C2	174.1 (19)
O4—Cd1—O1—C1	85.8 (2)	O4—Cd1—C1—C2	47.9 (18)
C4—Cd1—O1—C1	94.03 (17)	C4—Cd1—C1—C2	73.4 (18)
N1—Cd1—O2—C1	52.7 (2)	O1—C1—C2—C5	24.9 (4)
O3—Cd1—O2—C1	−82.47 (16)	O2—C1—C2—C5	−158.1 (3)
O4^i—Cd1—O2—C1	147.99 (15)	Cd1—C1—C2—C5	−148.9 (17)
O1—Cd1—O2—C1	2.15 (14)	O1—C1—C2—C3	148.6 (3)
O4—Cd1—O2—C1	−138.33 (15)	O2—C1—C2—C3	−34.3 (3)
C4—Cd1—O2—C1	−109.26 (15)	Cd1—C1—C2—C3	−25.2 (19)
N1—Cd1—O3—C4	99.30 (19)	O1—C1—C2—C6	−93.3 (3)
O2—Cd1—O3—C4	−109.63 (19)	O2—C1—C2—C6	83.7 (3)
O4^i—Cd1—O3—C4	−2.4 (2)	Cd1—C1—C2—C6	92.8 (18)
O1—Cd1—O3—C4	−165.21 (19)	C5—C2—C3—C4^ii	69.4 (3)
O4—Cd1—O3—C4	3.77 (17)	C1—C2—C3—C4^ii	−54.8 (3)
C1—Cd1—O3—C4	−137.98 (19)	C6—C2—C3—C4^ii	−172.2 (3)
N1—Cd1—O4—C4	−104.13 (18)	Cd1—O3—C4—O4	−6.8 (3)
O2—Cd1—O4—C4	83.32 (19)	Cd1—O3—C4—C3^ii	174.3 (2)
O3—Cd1—O4—C4	−3.68 (16)	Cd1^i—O4—C4—O3	159.6 (6)
O4^i—Cd1—O4—C4	171.1 (2)	Cd1—O4—C4—O3	6.4 (3)
O1—Cd1—O4—C4	15.9 (3)	Cd1^i—O4—C4—C3^ii	−21.5 (9)
C1—Cd1—O4—C4	56.7 (2)	Cd1—O4—C4—C3^ii	−174.7 (2)
N1—Cd1—O4—Cd1^i	84.77 (11)	Cd1^i—O4—C4—Cd1	153.2 (8)
O2—Cd1—O4—Cd1^i	−87.78 (11)	N1—Cd1—C4—O3	−89.4 (2)
O3—Cd1—O4—Cd1^i	−174.78 (17)	O2—Cd1—C4—O3	78.2 (2)
O4^i—Cd1—O4—Cd1^i	0.0	O4^i—Cd1—C4—O3	178.0 (2)
O1—Cd1—O4—Cd1^i	−155.21 (8)	O1—Cd1—C4—O3	16.9 (2)
C1—Cd1—O4—Cd1^i	−114.35 (11)	O4—Cd1—C4—O3	−173.4 (3)
C4—Cd1—O4—Cd1^i	−171.1 (2)	C1—Cd1—C4—O3	48.0 (2)
O2—Cd1—N1—C7	96.3 (3)	N1—Cd1—C4—O4	83.99 (19)
O3—Cd1—N1—C7	−129.5 (2)	O2—Cd1—C4—O4	−108.44 (18)
O4^i—Cd1—N1—C7	−1.3 (2)	O3—Cd1—C4—O4	173.4 (3)
O1—Cd1—N1—C7	136.2 (2)	O4^i—Cd1—C4—O4	−8.6 (2)
O4—Cd1—N1—C7	−73.5 (2)	O1—Cd1—C4—O4	−169.76 (17)
C1—Cd1—N1—C7	121.7 (2)	C1—Cd1—C4—O4	−138.60 (18)
C4—Cd1—N1—C7	−101.6 (2)	N1—Cd1—C4—C3^ii	−169 (2)
O2—Cd1—N1—C9	−76.8 (3)	O2—Cd1—C4—C3^ii	−1 (2)
O3—Cd1—N1—C9	57.4 (2)	O3—Cd1—C4—C3^ii	−80 (2)
O4^i—Cd1—N1—C9	−174.5 (2)	O4^i—Cd1—C4—C3^ii	98 (2)
O1—Cd1—N1—C9	−37.0 (2)	O1—Cd1—C4—C3^ii	−63 (2)
O4—Cd1—N1—C9	113.3 (2)	O4—Cd1—C4—C3^ii	107 (2)
C1—Cd1—N1—C9	−51.5 (3)	C1—Cd1—C4—C3^ii	−32 (2)
C4—Cd1—N1—C9	85.3 (2)	C9—N1—C7—N2	0.0 (3)
Cd1—O1—C1—O2	3.8 (2)	Cd1—N1—C7—N2	−174.09 (17)
Cd1—O1—C1—C2	−179.3 (2)	C8—N2—C7—N1	0.0 (3)
Cd1—O2—C1—O1	−4.1 (3)	C10—N2—C7—N1	176.2 (2)
Cd1—O2—C1—C2	178.9 (2)	C7—N2—C8—C9	0.0 (3)
N1—Cd1—C1—O1	32.60 (19)	C10—N2—C8—C9	−176.2 (2)
O2—Cd1—C1—O1	176.2 (3)	N2—C8—C9—N1	0.0 (4)
O3—Cd1—C1—O1	−81.08 (17)	C7—N1—C9—C8	0.0 (3)
O4^i—Cd1—C1—O1	139.02 (16)	Cd1—N1—C9—C8	174.58 (19)
O4—Cd1—C1—O1	−126.24 (16)	C7—N2—C10—C11	−93.5 (3)
C4—Cd1—C1—O1	−100.76 (17)	C8—N2—C10—C11	82.0 (3)
N1—Cd1—C1—O2	−143.55 (15)	N2—C10—C11—C13	96.7 (3)
O3—Cd1—C1—O2	102.77 (16)	N2—C10—C11—C12	−83.8 (3)
O4^i—Cd1—C1—O2	−37.14 (17)	C13—C11—C12—C12^iii	0.7 (5)
O1—Cd1—C1—O2	−176.2 (3)	C10—C11—C12—C12^iii	−178.9 (3)
O4—Cd1—C1—O2	57.60 (19)	C12—C11—C13—C13^iii	−1.2 (5)
C4—Cd1—C1—O2	83.08 (17)	C10—C11—C13—C13^iii	178.4 (3)
N1—Cd1—C1—C2	−153.3 (18)

Symmetry codes: (i) −x+3/2, −y+1/2, −z+2; (ii) −x+1, y, −z+3/2; (iii) −x+3, y, −z+5/2.