A fourfold inter­penetrating three-dimensional cadmium(II) coordination polymer: synthesis, crystal structure and physical properties

A novel three-dimensional Cd^II coordination framework, namely, poly[{μ-bis­[4-(2-methyl­imidazol-1-yl)phenyl] ether-κ²N³:N^3′}(μ-naphthalene-1,4-di­car­box­yl­ato-κ³O¹:O⁴,O^4′)cadmium(II)], [Cd(C₁₂H₆O₄)(C₂₀H₁₈N₄O)]_n or [Cd(1,4-NDC)(BMIOPE)]_n, where 1,4-H₂NDC is naphthalene-1,4-di­carb­oxy­lic acid and BMIOPE is bis­[4-(2-methyl­imidazol-1-yl)phenyl] ether, has been prepared and characterized by single-crystal X-ray diffraction, elemental analysis, IR spectroscopy and thermogravimetric analysis. The com­pound displays a novel fourfold inter­penetrating diamond-like network. In addition, it not only shows a strong fluorescence emission in the solid state, but also exhibits excellent photocatalytic activity for the degradation of methylene blue (MB) at room temperature.

Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2010) and TOPOS (Blatov & Shevchenko, 2006).

Poly[{µ-bis[4-(2-methylimidazol-1-yl)phenyl] ether-κ²N³:N^3'}(µ-naphthalene-1,4-dicarboxylato-κ³O¹:O⁴,O^4')cadmium(II)]

Crystal data

[Cd(C12H6O4)(C20H18N4O)]	Dx = 1.523 Mg m^−3
Mr = 656.96	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43	Cell parameters from 9690 reflections
a = 10.6631 (6) Å	θ = 2.7–27.5°
c = 25.203 (2) Å	µ = 0.81 mm^−1
V = 2865.6 (4) Å^3	T = 298 K
Z = 4	Block, colorless
F(000) = 1328	0.21 × 0.20 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer	5479 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.025
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θmax = 26.0°, θmin = 2.7°
Tmin = 0.651, Tmax = 0.746	h = −13→13
183838 measured reflections	k = −13→13
5614 independent reflections	l = −31→31

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)] = 0.026	H-atom parameters constrained
wR(F^2) = 0.066	w = 1/[σ^2(Fo^2) + (0.0312P)^2 + 1.795P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
5614 reflections	Δρmax = 0.60 e Å^−3
381 parameters	Δρmin = −0.35 e Å^−3
1 restraint	Absolute structure: Flack x determined using 2652 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.009 (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
C1	0.3840 (6)	0.4034 (5)	0.6654 (2)	0.0606 (14)
C2	0.4328 (5)	0.2940 (5)	0.69762 (18)	0.0503 (11)
C3	0.3787 (5)	0.2754 (6)	0.7465 (2)	0.0628 (14)
H3	0.3161	0.3294	0.7583	0.075*
C4	0.4172 (6)	0.1752 (6)	0.7788 (2)	0.0645 (15)
H4	0.3814	0.1654	0.8122	0.077*
C5	0.5055 (5)	0.0924 (5)	0.76245 (18)	0.0481 (10)
C6	0.5618 (4)	0.1062 (4)	0.71158 (17)	0.0405 (9)
C7	0.6522 (4)	0.0218 (4)	0.69172 (19)	0.0489 (10)
H7	0.6771	−0.0454	0.7128	0.059*
C8	0.7036 (5)	0.0354 (6)	0.6433 (2)	0.0644 (14)
H8	0.7629	−0.0218	0.6313	0.077*
C9	0.6669 (6)	0.1369 (6)	0.6111 (2)	0.0685 (15)
H9	0.7019	0.1460	0.5775	0.082*
C10	0.5815 (5)	0.2213 (6)	0.62837 (19)	0.0608 (13)
H10	0.5593	0.2881	0.6066	0.073*
C11	0.5250 (4)	0.2098 (4)	0.67914 (17)	0.0439 (9)
C12	0.5434 (5)	−0.0112 (5)	0.79977 (18)	0.0502 (11)
C13	0.4820 (5)	0.7762 (6)	0.6178 (2)	0.0668 (13)
H13A	0.4132	0.7796	0.6424	0.100*
H13B	0.5152	0.8590	0.6128	0.100*
H13C	0.5463	0.7225	0.6317	0.100*
C14	0.4372 (5)	0.7259 (4)	0.56611 (18)	0.0469 (10)
C15	0.3321 (6)	0.6281 (5)	0.5058 (2)	0.0621 (14)
H15	0.2707	0.5791	0.4897	0.075*
C16	0.4287 (7)	0.6818 (6)	0.4807 (2)	0.0720 (17)
H16	0.4471	0.6779	0.4447	0.086*
C17	0.5998 (5)	0.8275 (5)	0.5092 (2)	0.0536 (11)
C18	0.7196 (5)	0.8008 (5)	0.5262 (2)	0.0574 (12)
H18	0.7345	0.7303	0.5470	0.069*
C19	0.8174 (5)	0.8792 (5)	0.5123 (2)	0.0551 (12)
H19	0.8985	0.8621	0.5238	0.066*
C20	0.7937 (5)	0.9826 (5)	0.48151 (18)	0.0509 (11)
C21	0.6730 (5)	1.0130 (5)	0.4663 (2)	0.0623 (14)
H21	0.6574	1.0860	0.4472	0.075*
C22	0.5754 (5)	0.9336 (6)	0.4799 (3)	0.0680 (16)
H22	0.4939	0.9519	0.4694	0.082*
C23	0.9009 (5)	1.0987 (5)	0.41525 (19)	0.0508 (11)
C24	0.8614 (6)	1.0230 (5)	0.3748 (2)	0.0697 (15)
H24	0.8261	0.9451	0.3820	0.084*
C25	0.8745 (7)	1.0634 (5)	0.3233 (2)	0.0676 (16)
H25	0.8492	1.0120	0.2954	0.081*
C26	0.9246 (4)	1.1787 (5)	0.31282 (19)	0.0487 (10)
C27	0.9610 (6)	1.2548 (6)	0.3539 (2)	0.0745 (18)
H27	0.9944	1.3335	0.3467	0.089*
C28	0.9485 (7)	1.2156 (7)	0.4054 (2)	0.0755 (19)
H28	0.9721	1.2677	0.4333	0.091*
C29	0.7199 (6)	1.3199 (8)	0.2552 (3)	0.083 (2)
H29A	0.6680	1.3569	0.2283	0.125*
H29B	0.7339	1.3796	0.2831	0.125*
H29C	0.6789	1.2472	0.2695	0.125*
C30	0.8427 (4)	1.2826 (5)	0.23156 (18)	0.0477 (11)
C31	1.0314 (5)	1.2001 (5)	0.2247 (2)	0.0610 (13)
H31	1.1066	1.1600	0.2327	0.073*
C32	0.9975 (5)	1.2495 (5)	0.1779 (2)	0.0606 (14)
H32	1.0464	1.2490	0.1473	0.073*
Cd1	0.20681 (3)	0.57736 (3)	0.61870 (2)	0.04114 (9)
N1	0.3372 (4)	0.6566 (4)	0.55918 (16)	0.0517 (10)
N2	0.4957 (4)	0.7442 (4)	0.51948 (18)	0.0576 (11)
N3	0.9320 (4)	1.2208 (4)	0.25840 (17)	0.0489 (9)
N4	0.8788 (4)	1.3016 (4)	0.18177 (15)	0.0457 (9)
O1	0.2738 (4)	0.4285 (5)	0.6697 (2)	0.0894 (16)
O2	0.4579 (6)	0.4704 (6)	0.6406 (3)	0.130 (3)
O3	0.4609 (4)	−0.0745 (5)	0.8203 (2)	0.0839 (14)
O4	0.6577 (4)	−0.0308 (4)	0.80877 (18)	0.0804 (14)
O5	0.8929 (4)	1.0599 (4)	0.46781 (14)	0.0637 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.074 (4)	0.063 (3)	0.044 (3)	0.019 (3)	−0.002 (2)	0.016 (2)
C2	0.060 (3)	0.054 (3)	0.038 (2)	0.007 (2)	−0.002 (2)	0.015 (2)
C3	0.070 (3)	0.072 (4)	0.046 (3)	0.025 (3)	0.012 (3)	0.014 (2)
C4	0.078 (4)	0.079 (4)	0.036 (2)	0.018 (3)	0.013 (2)	0.021 (2)
C5	0.053 (3)	0.055 (3)	0.037 (2)	0.000 (2)	−0.0040 (19)	0.012 (2)
C6	0.043 (2)	0.045 (2)	0.0338 (19)	−0.0012 (17)	−0.0052 (16)	0.0057 (16)
C7	0.050 (2)	0.047 (2)	0.049 (3)	0.0036 (19)	−0.003 (2)	0.006 (2)
C8	0.066 (3)	0.071 (3)	0.056 (3)	0.008 (3)	0.011 (2)	−0.003 (3)
C9	0.075 (3)	0.092 (4)	0.038 (3)	0.011 (3)	0.016 (3)	0.010 (3)
C10	0.069 (3)	0.077 (3)	0.037 (3)	0.006 (3)	0.001 (2)	0.020 (2)
C11	0.047 (2)	0.051 (2)	0.033 (2)	−0.0003 (19)	−0.0046 (18)	0.0091 (18)
C12	0.061 (3)	0.053 (3)	0.037 (2)	0.003 (2)	−0.003 (2)	0.015 (2)
C13	0.072 (3)	0.082 (3)	0.046 (2)	−0.017 (3)	−0.002 (3)	0.002 (3)
C14	0.057 (3)	0.045 (2)	0.039 (2)	−0.002 (2)	−0.0018 (19)	0.0081 (18)
C15	0.078 (4)	0.063 (3)	0.045 (3)	−0.014 (3)	0.001 (3)	−0.002 (2)
C16	0.097 (5)	0.072 (4)	0.047 (3)	−0.017 (3)	0.005 (3)	−0.007 (3)
C17	0.056 (3)	0.056 (3)	0.049 (3)	0.001 (2)	0.012 (2)	0.009 (2)
C18	0.060 (3)	0.061 (3)	0.051 (3)	0.018 (2)	0.007 (2)	0.018 (2)
C19	0.046 (2)	0.072 (3)	0.047 (3)	0.015 (2)	0.003 (2)	0.013 (2)
C20	0.053 (3)	0.066 (3)	0.034 (2)	−0.003 (2)	0.0041 (19)	0.010 (2)
C21	0.052 (3)	0.065 (3)	0.070 (3)	0.004 (2)	−0.001 (2)	0.026 (3)
C22	0.050 (3)	0.073 (4)	0.081 (4)	0.007 (2)	0.003 (3)	0.029 (3)
C23	0.045 (2)	0.069 (3)	0.039 (2)	−0.007 (2)	0.0002 (18)	0.011 (2)
C24	0.112 (5)	0.050 (3)	0.047 (3)	−0.013 (3)	0.007 (3)	0.008 (2)
C25	0.114 (5)	0.049 (3)	0.040 (3)	−0.012 (3)	0.007 (3)	−0.003 (2)
C26	0.050 (3)	0.059 (3)	0.037 (2)	−0.003 (2)	0.0065 (18)	0.011 (2)
C27	0.085 (4)	0.081 (4)	0.058 (4)	−0.041 (3)	−0.001 (3)	0.014 (3)
C28	0.088 (4)	0.093 (5)	0.044 (3)	−0.042 (4)	−0.010 (3)	0.002 (3)
C29	0.056 (3)	0.139 (6)	0.054 (3)	0.021 (4)	0.021 (3)	0.032 (4)
C30	0.046 (2)	0.061 (3)	0.036 (2)	0.000 (2)	0.0074 (19)	0.005 (2)
C31	0.057 (3)	0.069 (3)	0.057 (3)	0.017 (2)	0.022 (2)	0.016 (3)
C32	0.073 (3)	0.059 (3)	0.050 (3)	0.016 (3)	0.028 (3)	0.012 (2)
Cd1	0.04676 (17)	0.04359 (16)	0.03307 (13)	−0.00448 (12)	−0.00818 (13)	0.00357 (12)
N1	0.067 (3)	0.049 (2)	0.040 (2)	−0.0060 (19)	−0.0018 (18)	0.0058 (17)
N2	0.063 (3)	0.061 (3)	0.049 (2)	−0.005 (2)	0.006 (2)	0.009 (2)
N3	0.052 (2)	0.053 (2)	0.042 (2)	−0.0002 (18)	0.0130 (16)	0.0094 (17)
N4	0.053 (2)	0.050 (2)	0.0337 (19)	−0.0004 (17)	0.0113 (16)	0.0033 (16)
O1	0.062 (3)	0.098 (3)	0.108 (4)	0.026 (2)	0.008 (2)	0.059 (3)
O2	0.113 (4)	0.121 (5)	0.157 (6)	0.028 (4)	0.031 (4)	0.097 (5)
O3	0.061 (2)	0.092 (3)	0.099 (3)	0.011 (2)	0.011 (2)	0.054 (3)
O4	0.068 (3)	0.094 (3)	0.079 (3)	−0.009 (2)	−0.025 (2)	0.048 (2)
O5	0.056 (2)	0.099 (3)	0.0355 (17)	−0.0178 (19)	−0.0047 (14)	0.0188 (18)

Geometric parameters (Å, º)

C1—O1	1.210 (7)	C19—C20	1.371 (7)
C1—O2	1.234 (8)	C19—H19	0.9300
C1—C2	1.513 (6)	C20—C21	1.382 (7)
C2—C3	1.376 (7)	C20—O5	1.385 (6)
C2—C11	1.410 (7)	C21—C22	1.384 (8)
C3—C4	1.405 (7)	C21—H21	0.9300
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.355 (7)	C23—C24	1.366 (8)
C4—H4	0.9300	C23—C28	1.368 (8)
C5—C6	1.423 (6)	C23—O5	1.390 (6)
C5—C12	1.506 (6)	C24—C25	1.376 (8)
C6—C7	1.411 (7)	C24—H24	0.9300
C6—C11	1.429 (6)	C25—C26	1.366 (7)
C7—C8	1.344 (8)	C25—H25	0.9300
C7—H7	0.9300	C26—C27	1.371 (8)
C8—C9	1.409 (8)	C26—N3	1.445 (6)
C8—H8	0.9300	C27—C28	1.371 (8)
C9—C10	1.353 (8)	C27—H27	0.9300
C9—H9	0.9300	C28—H28	0.9300
C10—C11	1.419 (6)	C29—C30	1.492 (7)
C10—H10	0.9300	C29—H29A	0.9600
C12—O3	1.224 (6)	C29—H29B	0.9600
C12—O4	1.257 (6)	C29—H29C	0.9600
C12—Cd1^i	2.739 (4)	C30—N4	1.328 (6)
C13—C14	1.488 (8)	C30—N3	1.342 (6)
C13—H13A	0.9600	C31—C32	1.342 (8)
C13—H13B	0.9600	C31—N3	1.376 (6)
C13—H13C	0.9600	C31—H31	0.9300
C14—N1	1.310 (6)	C32—N4	1.386 (7)
C14—N2	1.344 (6)	C32—H32	0.9300
C15—C16	1.337 (9)	Cd1—O1	2.164 (4)
C15—N1	1.381 (7)	Cd1—N1	2.213 (4)
C15—H15	0.9300	Cd1—N4^ii	2.242 (4)
C16—N2	1.380 (8)	Cd1—O3^iii	2.240 (4)
C16—H16	0.9300	Cd1—O4^iii	2.557 (4)
C17—C18	1.377 (7)	Cd1—C12^iii	2.739 (4)
C17—C22	1.375 (8)	N4—Cd1^iv	2.242 (4)
C17—N2	1.446 (7)	O3—Cd1^i	2.240 (4)
C18—C19	1.382 (8)	O4—Cd1^i	2.557 (4)
C18—H18	0.9300
O1—C1—O2	122.5 (5)	C20—C21—H21	120.4
O1—C1—C2	117.2 (5)	C17—C22—C21	119.6 (5)
O2—C1—C2	119.9 (5)	C17—C22—H22	120.2
C3—C2—C11	119.8 (4)	C21—C22—H22	120.2
C3—C2—C1	116.6 (5)	C24—C23—C28	121.2 (5)
C11—C2—C1	123.6 (4)	C24—C23—O5	121.1 (5)
C2—C3—C4	120.4 (5)	C28—C23—O5	117.8 (5)
C2—C3—H3	119.8	C23—C24—C25	119.2 (5)
C4—C3—H3	119.8	C23—C24—H24	120.4
C5—C4—C3	121.5 (5)	C25—C24—H24	120.4
C5—C4—H4	119.3	C26—C25—C24	120.2 (5)
C3—C4—H4	119.3	C26—C25—H25	119.9
C4—C5—C6	120.0 (4)	C24—C25—H25	119.9
C4—C5—C12	118.3 (4)	C27—C26—C25	119.8 (5)
C6—C5—C12	121.7 (4)	C27—C26—N3	121.2 (5)
C7—C6—C5	122.8 (4)	C25—C26—N3	118.9 (5)
C7—C6—C11	118.5 (4)	C26—C27—C28	120.5 (5)
C5—C6—C11	118.7 (4)	C26—C27—H27	119.7
C8—C7—C6	122.1 (5)	C28—C27—H27	119.7
C8—C7—H7	119.0	C23—C28—C27	119.0 (6)
C6—C7—H7	119.0	C23—C28—H28	120.5
C7—C8—C9	119.5 (5)	C27—C28—H28	120.5
C7—C8—H8	120.2	C30—C29—H29A	109.5
C9—C8—H8	120.2	C30—C29—H29B	109.5
C10—C9—C8	120.8 (5)	H29A—C29—H29B	109.5
C10—C9—H9	119.6	C30—C29—H29C	109.5
C8—C9—H9	119.6	H29A—C29—H29C	109.5
C9—C10—C11	121.2 (5)	H29B—C29—H29C	109.5
C9—C10—H10	119.4	N4—C30—N3	110.2 (4)
C11—C10—H10	119.4	N4—C30—C29	126.2 (5)
C2—C11—C10	122.6 (4)	N3—C30—C29	123.5 (4)
C2—C11—C6	119.6 (4)	C32—C31—N3	105.8 (5)
C10—C11—C6	117.8 (4)	C32—C31—H31	127.1
O3—C12—O4	121.9 (4)	N3—C31—H31	127.1
O3—C12—C5	118.4 (5)	C31—C32—N4	110.0 (4)
O4—C12—C5	119.7 (4)	C31—C32—H32	125.0
O3—C12—Cd1^i	53.6 (3)	N4—C32—H32	125.0
O4—C12—Cd1^i	68.3 (3)	O1—Cd1—N1	118.37 (17)
C5—C12—Cd1^i	172.0 (4)	O1—Cd1—N4^ii	97.78 (19)
C14—C13—H13A	109.5	N1—Cd1—N4^ii	121.12 (16)
C14—C13—H13B	109.5	O1—Cd1—O3^iii	97.2 (2)
H13A—C13—H13B	109.5	N1—Cd1—O3^iii	103.80 (19)
C14—C13—H13C	109.5	N4^ii—Cd1—O3^iii	116.65 (19)
H13A—C13—H13C	109.5	O1—Cd1—O4^iii	147.02 (19)
H13B—C13—H13C	109.5	N1—Cd1—O4^iii	86.17 (17)
N1—C14—N2	110.0 (4)	N4^ii—Cd1—O4^iii	85.83 (14)
N1—C14—C13	125.6 (4)	O3^iii—Cd1—O4^iii	53.26 (14)
N2—C14—C13	124.4 (5)	O1—Cd1—C12^iii	122.09 (19)
C16—C15—N1	109.5 (5)	N1—Cd1—C12^iii	95.70 (15)
C16—C15—H15	125.2	N4^ii—Cd1—C12^iii	102.46 (15)
N1—C15—H15	125.2	O3^iii—Cd1—C12^iii	26.09 (15)
C15—C16—N2	105.8 (5)	O4^iii—Cd1—C12^iii	27.18 (14)
C15—C16—H16	127.1	C14—N1—C15	106.7 (4)
N2—C16—H16	127.1	C14—N1—Cd1	129.6 (3)
C18—C17—C22	120.8 (5)	C15—N1—Cd1	123.5 (4)
C18—C17—N2	122.0 (5)	C14—N2—C16	108.0 (5)
C22—C17—N2	117.2 (5)	C14—N2—C17	127.0 (5)
C17—C18—C19	119.7 (5)	C16—N2—C17	124.5 (5)
C17—C18—H18	120.1	C30—N3—C31	108.3 (4)
C19—C18—H18	120.1	C30—N3—C26	126.3 (4)
C20—C19—C18	119.4 (5)	C31—N3—C26	125.4 (4)
C20—C19—H19	120.3	C30—N4—C32	105.7 (4)
C18—C19—H19	120.3	C30—N4—Cd1^iv	129.8 (3)
C19—C20—C21	121.1 (5)	C32—N4—Cd1^iv	123.5 (3)
C19—C20—O5	118.6 (5)	C1—O1—Cd1	115.4 (4)
C21—C20—O5	120.2 (5)	C12—O3—Cd1^i	100.4 (3)
C22—C21—C20	119.2 (5)	C12—O4—Cd1^i	84.5 (3)
C22—C21—H21	120.4	C20—O5—C23	117.5 (4)
O1—C1—C2—C3	−33.8 (8)	C25—C26—C27—C28	0.5 (10)
O2—C1—C2—C3	138.7 (7)	N3—C26—C27—C28	177.3 (6)
O1—C1—C2—C11	143.4 (6)	C24—C23—C28—C27	−2.6 (11)
O2—C1—C2—C11	−44.1 (9)	O5—C23—C28—C27	178.1 (6)
C11—C2—C3—C4	1.9 (9)	C26—C27—C28—C23	1.0 (11)
C1—C2—C3—C4	179.2 (6)	N3—C31—C32—N4	0.3 (7)
C2—C3—C4—C5	−1.9 (10)	N2—C14—N1—C15	0.6 (6)
C3—C4—C5—C6	0.3 (9)	C13—C14—N1—C15	−178.5 (5)
C3—C4—C5—C12	178.9 (6)	N2—C14—N1—Cd1	174.4 (3)
C4—C5—C6—C7	−178.6 (5)	C13—C14—N1—Cd1	−4.7 (8)
C12—C5—C6—C7	2.7 (7)	C16—C15—N1—C14	−0.6 (7)
C4—C5—C6—C11	1.3 (7)	C16—C15—N1—Cd1	−174.9 (4)
C12—C5—C6—C11	−177.4 (4)	N1—C14—N2—C16	−0.4 (6)
C5—C6—C7—C8	179.3 (5)	C13—C14—N2—C16	178.7 (5)
C11—C6—C7—C8	−0.6 (7)	N1—C14—N2—C17	171.8 (5)
C6—C7—C8—C9	0.1 (9)	C13—C14—N2—C17	−9.1 (8)
C7—C8—C9—C10	0.6 (10)	C15—C16—N2—C14	0.0 (7)
C8—C9—C10—C11	−0.7 (10)	C15—C16—N2—C17	−172.4 (5)
C3—C2—C11—C10	177.8 (6)	C18—C17—N2—C14	73.6 (7)
C1—C2—C11—C10	0.7 (8)	C22—C17—N2—C14	−108.5 (7)
C3—C2—C11—C6	−0.3 (8)	C18—C17—N2—C16	−115.4 (7)
C1—C2—C11—C6	−177.5 (5)	C22—C17—N2—C16	62.5 (8)
C9—C10—C11—C2	−178.0 (6)	N4—C30—N3—C31	0.7 (6)
C9—C10—C11—C6	0.2 (8)	C29—C30—N3—C31	179.2 (6)
C7—C6—C11—C2	178.7 (5)	N4—C30—N3—C26	−177.2 (5)
C5—C6—C11—C2	−1.2 (7)	C29—C30—N3—C26	1.3 (9)
C7—C6—C11—C10	0.4 (7)	C32—C31—N3—C30	−0.6 (7)
C5—C6—C11—C10	−179.5 (5)	C32—C31—N3—C26	177.3 (5)
C4—C5—C12—O3	50.3 (8)	C27—C26—N3—C30	−88.8 (7)
C6—C5—C12—O3	−131.0 (6)	C25—C26—N3—C30	88.0 (7)
C4—C5—C12—O4	−130.1 (6)	C27—C26—N3—C31	93.6 (7)
C6—C5—C12—O4	48.6 (7)	C25—C26—N3—C31	−89.6 (7)
N1—C15—C16—N2	0.3 (7)	N3—C30—N4—C32	−0.5 (6)
C22—C17—C18—C19	−2.1 (9)	C29—C30—N4—C32	−178.9 (6)
N2—C17—C18—C19	175.7 (5)	N3—C30—N4—Cd1^iv	−169.2 (3)
C17—C18—C19—C20	−0.3 (8)	C29—C30—N4—Cd1^iv	12.4 (8)
C18—C19—C20—C21	3.3 (9)	C31—C32—N4—C30	0.1 (6)
C18—C19—C20—O5	−179.8 (5)	C31—C32—N4—Cd1^iv	169.7 (4)
C19—C20—C21—C22	−3.9 (9)	O2—C1—O1—Cd1	11.7 (10)
O5—C20—C21—C22	179.3 (6)	C2—C1—O1—Cd1	−176.0 (4)
C18—C17—C22—C21	1.6 (10)	O4—C12—O3—Cd1^i	0.0 (7)
N2—C17—C22—C21	−176.3 (6)	C5—C12—O3—Cd1^i	179.6 (4)
C20—C21—C22—C17	1.4 (10)	O3—C12—O4—Cd1^i	0.0 (6)
C28—C23—C24—C25	2.6 (10)	C5—C12—O4—Cd1^i	−179.6 (4)
O5—C23—C24—C25	−178.0 (6)	C19—C20—O5—C23	134.5 (5)
C23—C24—C25—C26	−1.1 (10)	C21—C20—O5—C23	−48.5 (7)
C24—C25—C26—C27	−0.5 (10)	C24—C23—O5—C20	−32.7 (8)
C24—C25—C26—N3	−177.3 (6)	C28—C23—O5—C20	146.6 (6)

Symmetry codes: (i) y, −x, z+1/4; (ii) −x+1, −y+2, z+1/2; (iii) −y, x, z−1/4; (iv) −x+1, −y+2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O1^v	0.93	2.31	3.207 (7)	162
C25—H25···O5^vi	0.93	2.53	3.295 (7)	140
C32—H32···O4^vii	0.93	2.58	3.175 (7)	122

Symmetry codes: (v) −y+1, x+1, z−1/4; (vi) −y+2, x, z−1/4; (vii) y+1, −x+2, z−3/4.