`0'- and `8'-shaped complexes generated from a nano-sized oxa­diazole-containing organic ligand with CdI₂ and CuI

A new nano-sized rigid double-armed oxa­diazole-bridged organic ligand, 2,5-bis­{2-methyl-5-[2-(pyridin-3-yl)ethen­yl]phen­yl}-1,3,4-oxa­diazole, C₃₀H₂₀N₄O, L or (I), which adopts a cis conformation in the solid state, has been synthesized and used to create the two novel metallocycle complexes (2,5-bis­{2-methyl-5-[2-(pyridin-3-yl-κN)ethen­yl]phen­yl}-1,3,4-oxa­diazole)di­iodido­cadmium(II) di­chloro­methane monosolvate, [CdI₂(C₃₀H₂₀N₄O)]·CH₂Cl₂, (II), and di-μ-iodido-bis­[(2,5-bis­{2-methyl-5-[2-(pyridin-3-yl-κN)ethen­yl]phen­yl}-1,3,4-oxa­diazole)copper(I)], [Cu₂I₂(C₃₀H₂₀N₄O)₂], (III). Molecules of complex (II) adopts a 20-membered `0'-shaped metallocycle structure with crystallographic mirror symmetry. The discrete units are linked into one-dimensional chains through inter­molecular π–π and C—H...π inter­actions. In (III), the two I atoms and two Cu<sup>I</sup> atoms form a {Cu<sub>2</sub>(μ-I)<sub>2</sub>} cluster. One {Cu<sub>2</sub>(μ-I)<sub>2</sub>} cluster and two L ligands form two 20-membered monometallic rings in a head-to-head fashion, leading to a discrete centrosymmetric `8'-shaped metallocyclic complex. These metallocycles stack together via two kinds of inter­molecular π–π inter­actions to generate a two-dimensional network in the ac plane. The luminescence properties of (I)–(III) were investigated in the solid state at room temperature and displayed an obvious red shift.

Computing details

For all compounds, data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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).

(I) 2,5-Bis{2-methyl-5-[2-(pyridin-3-yl)ethenyl]phenyl}-1,3,4-oxadiazole

Crystal data

C30H20N4O	F(000) = 1888
Mr = 452.50	Dx = 1.301 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ac2ab	Cell parameters from 7328 reflections
a = 16.500 (6) Å	θ = 3.2–24.1°
b = 11.356 (4) Å	µ = 0.08 mm^−1
c = 24.656 (9) Å	T = 298 K
V = 4620 (3) Å^3	Block, colourless
Z = 8	0.50 × 0.48 × 0.45 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4337 independent reflections
Radiation source: fine-focus sealed tube	3078 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
phi and ω scans	θmax = 25.6°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −20→18
Tmin = 0.961, Tmax = 0.964	k = −13→12
22943 measured reflections	l = −29→28

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0655P)^2 + 0.2986P] where P = (Fo^2 + 2Fc^2)/3
4337 reflections	(Δ/σ)max < 0.001
318 parameters	Δρmax = 0.13 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Experimental. ¹H NMR (300 MHz, CDCl₃, 298 K, TMS): δ 8.80 (s, 2H, –C₅H₄N), 8.56–8.55(d, 2H, –C₅H₄N), 8.20 (s, 2H, –C₆H₃), 7.93–7.91 (d, 2H, –C₅H₄N), 7.60–7.57 (t, 2H, –C₅H₄N), 7.40–7.37 (d, 4H, –C₆H₃), 2.81 (s, 6H, –CH₃); IR (v, cm^-1): 2958 (w), 2918 (w), 2218 (w), 1675 (w), 1534 (s), 1498 (s), 1473 (m), 1438 (m), 1405 (m), 1379 (m), 1279 (w), 1235 (w), 1151 (w), 1047 (m), 1019 (m), 886 (w), 833(s), 800 (s), 746 (m), 725 (w), 697(vs), 621 (w), 576 (m), 548 (w).

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	0.01307 (12)	0.62219 (19)	0.32329 (7)	0.0730 (5)
H1	−0.0144	0.6743	0.3458	0.088*
C2	0.08306 (11)	0.66022 (17)	0.29947 (8)	0.0700 (5)
H2	0.1016	0.7366	0.3050	0.084*
C3	0.12532 (11)	0.58362 (15)	0.26722 (7)	0.0608 (4)
H3	0.1737	0.6068	0.2511	0.073*
C4	0.09528 (9)	0.47142 (14)	0.25900 (6)	0.0509 (4)
C5	0.02279 (11)	0.44355 (16)	0.28423 (7)	0.0613 (4)
H5	0.0013	0.3690	0.2783	0.074*
C6	0.13901 (10)	0.38952 (15)	0.22613 (7)	0.0582 (4)
C7	0.18106 (10)	0.32660 (15)	0.19946 (7)	0.0574 (4)
C8	0.23889 (10)	0.25793 (13)	0.16968 (6)	0.0520 (4)
C9	0.32031 (10)	0.28981 (14)	0.17117 (7)	0.0571 (4)
H9	0.3365	0.3564	0.1903	0.068*
C10	0.37656 (10)	0.22247 (15)	0.14426 (7)	0.0581 (4)
H10	0.4308	0.2442	0.1463	0.070*
C11	0.35630 (9)	0.12411 (14)	0.11429 (6)	0.0516 (4)
C12	0.42198 (10)	0.05354 (17)	0.08801 (9)	0.0721 (5)
H12A	0.4721	0.0963	0.0898	0.108*
H12B	0.4082	0.0392	0.0508	0.108*
H12C	0.4279	−0.0202	0.1066	0.108*
C13	0.27353 (9)	0.09465 (13)	0.11077 (6)	0.0469 (4)
C14	0.21659 (9)	0.16040 (14)	0.13915 (6)	0.0522 (4)
H14	0.1623	0.1386	0.1377	0.063*
C15	0.24435 (9)	−0.00179 (13)	0.07672 (6)	0.0467 (4)
C16	0.15499 (9)	−0.10815 (13)	0.03725 (6)	0.0453 (4)
C17	0.07296 (9)	−0.14592 (13)	0.02329 (6)	0.0456 (4)
C18	0.05727 (10)	−0.22923 (14)	−0.01741 (7)	0.0553 (4)
C19	0.12250 (12)	−0.28784 (18)	−0.05025 (8)	0.0820 (6)
H19A	0.0984	−0.3441	−0.0744	0.123*
H19B	0.1596	−0.3273	−0.0264	0.123*
H19C	0.1512	−0.2295	−0.0709	0.123*
C20	−0.02336 (11)	−0.25722 (16)	−0.02735 (7)	0.0654 (5)
H20	−0.0351	−0.3110	−0.0547	0.078*
C21	−0.08638 (10)	−0.20936 (15)	0.00123 (7)	0.0601 (4)
H21	−0.1394	−0.2315	−0.0066	0.072*
C22	−0.07114 (9)	−0.12788 (13)	0.04181 (6)	0.0485 (4)
C23	0.00886 (9)	−0.09666 (13)	0.05228 (6)	0.0463 (4)
H23	0.0198	−0.0417	0.0792	0.056*
C24	−0.13698 (10)	−0.07740 (14)	0.07199 (7)	0.0526 (4)
C25	−0.19375 (10)	−0.03916 (15)	0.09635 (7)	0.0555 (4)
C26	−0.26064 (9)	0.00418 (14)	0.12727 (6)	0.0512 (4)
C27	−0.30029 (10)	0.10792 (16)	0.11546 (8)	0.0683 (5)
H27	−0.2851	0.1526	0.0855	0.082*
C28	−0.36230 (11)	0.14450 (17)	0.14836 (9)	0.0786 (6)
H28	−0.3890	0.2150	0.1415	0.094*
C29	−0.38428 (13)	0.07613 (19)	0.19129 (9)	0.0831 (6)
H29	−0.4261	0.1023	0.2135	0.100*
C30	−0.28839 (11)	−0.05906 (16)	0.17151 (8)	0.0680 (5)
H30	−0.2626	−0.1297	0.1796	0.082*
N1	−0.01808 (9)	0.51617 (16)	0.31635 (6)	0.0711 (4)
N2	0.28331 (8)	−0.07945 (12)	0.04901 (6)	0.0614 (4)
N3	0.22460 (8)	−0.14916 (12)	0.02288 (6)	0.0600 (4)
N4	−0.34904 (11)	−0.02616 (16)	0.20313 (7)	0.0863 (5)
O1	0.16261 (6)	−0.01442 (9)	0.07135 (4)	0.0476 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0694 (12)	0.0876 (14)	0.0619 (12)	0.0130 (11)	0.0049 (9)	−0.0142 (10)
C2	0.0732 (12)	0.0583 (11)	0.0784 (12)	0.0009 (9)	0.0017 (10)	−0.0098 (10)
C3	0.0567 (10)	0.0590 (11)	0.0665 (11)	−0.0015 (9)	0.0088 (8)	0.0031 (9)
C4	0.0529 (9)	0.0537 (10)	0.0461 (9)	0.0025 (7)	−0.0015 (7)	0.0033 (7)
C5	0.0610 (10)	0.0658 (11)	0.0572 (10)	−0.0070 (9)	0.0020 (8)	0.0039 (9)
C6	0.0611 (10)	0.0562 (10)	0.0573 (10)	−0.0007 (8)	−0.0026 (8)	−0.0017 (8)
C7	0.0609 (10)	0.0536 (10)	0.0575 (10)	−0.0009 (8)	−0.0040 (8)	−0.0025 (8)
C8	0.0557 (10)	0.0493 (9)	0.0511 (9)	0.0005 (7)	−0.0023 (7)	0.0007 (7)
C9	0.0616 (10)	0.0542 (10)	0.0554 (10)	−0.0089 (8)	−0.0036 (8)	−0.0026 (8)
C10	0.0484 (9)	0.0656 (11)	0.0604 (10)	−0.0116 (8)	−0.0025 (8)	0.0011 (8)
C11	0.0453 (9)	0.0546 (9)	0.0550 (9)	−0.0024 (7)	0.0004 (7)	0.0052 (8)
C12	0.0458 (9)	0.0809 (13)	0.0895 (13)	−0.0020 (9)	0.0060 (9)	−0.0135 (11)
C13	0.0454 (8)	0.0462 (8)	0.0493 (8)	−0.0014 (7)	0.0012 (7)	0.0021 (7)
C14	0.0452 (8)	0.0529 (9)	0.0584 (10)	−0.0009 (7)	0.0004 (7)	−0.0020 (8)
C15	0.0390 (8)	0.0489 (9)	0.0523 (9)	0.0005 (7)	0.0041 (7)	0.0028 (7)
C16	0.0505 (9)	0.0411 (8)	0.0444 (8)	−0.0010 (7)	0.0067 (7)	−0.0022 (6)
C17	0.0483 (8)	0.0447 (8)	0.0440 (8)	−0.0027 (7)	0.0032 (7)	0.0010 (7)
C18	0.0596 (10)	0.0524 (10)	0.0540 (9)	−0.0061 (8)	0.0069 (8)	−0.0086 (8)
C19	0.0783 (13)	0.0839 (14)	0.0838 (14)	−0.0110 (11)	0.0175 (11)	−0.0389 (11)
C20	0.0704 (12)	0.0633 (11)	0.0623 (11)	−0.0144 (9)	0.0019 (9)	−0.0170 (9)
C21	0.0548 (10)	0.0623 (10)	0.0630 (10)	−0.0121 (8)	−0.0031 (8)	−0.0029 (9)
C22	0.0473 (9)	0.0481 (9)	0.0501 (9)	−0.0035 (7)	0.0016 (7)	0.0049 (7)
C23	0.0483 (9)	0.0463 (8)	0.0441 (8)	−0.0012 (7)	0.0003 (7)	−0.0018 (7)
C24	0.0450 (9)	0.0559 (10)	0.0567 (10)	−0.0042 (7)	−0.0015 (8)	0.0060 (8)
C25	0.0447 (9)	0.0626 (10)	0.0593 (10)	−0.0058 (8)	−0.0023 (8)	0.0024 (8)
C26	0.0401 (8)	0.0587 (10)	0.0549 (9)	−0.0064 (7)	−0.0016 (7)	−0.0008 (8)
C27	0.0591 (11)	0.0722 (12)	0.0736 (12)	0.0023 (9)	0.0144 (9)	0.0199 (10)
C28	0.0686 (12)	0.0660 (12)	0.1011 (15)	0.0109 (10)	0.0273 (11)	0.0199 (11)
C29	0.0795 (14)	0.0797 (14)	0.0901 (15)	0.0095 (11)	0.0349 (12)	0.0100 (12)
C30	0.0647 (11)	0.0650 (11)	0.0742 (12)	0.0055 (9)	0.0095 (9)	0.0133 (9)
N1	0.0616 (9)	0.0932 (12)	0.0585 (9)	−0.0006 (9)	0.0093 (7)	−0.0021 (8)
N2	0.0451 (8)	0.0647 (9)	0.0743 (9)	−0.0012 (7)	0.0073 (7)	−0.0164 (8)
N3	0.0492 (8)	0.0641 (9)	0.0666 (9)	0.0004 (7)	0.0086 (7)	−0.0154 (7)
N4	0.0876 (12)	0.0878 (12)	0.0836 (12)	0.0143 (10)	0.0316 (10)	0.0252 (9)
O1	0.0421 (6)	0.0466 (6)	0.0539 (6)	−0.0007 (4)	0.0034 (4)	−0.0053 (5)

Geometric parameters (Å, º)

C1—N1	1.320 (2)	C16—O1	1.3622 (17)
C1—C2	1.366 (3)	C16—C17	1.461 (2)
C1—H1	0.9300	C17—C23	1.394 (2)
C2—C3	1.369 (2)	C17—C18	1.403 (2)
C2—H2	0.9300	C18—C20	1.390 (2)
C3—C4	1.382 (2)	C18—C19	1.502 (2)
C3—H3	0.9300	C19—H19A	0.9600
C4—C5	1.385 (2)	C19—H19B	0.9600
C4—C6	1.429 (2)	C19—H19C	0.9600
C5—N1	1.327 (2)	C20—C21	1.369 (2)
C5—H5	0.9300	C20—H20	0.9300
C6—C7	1.193 (2)	C21—C22	1.386 (2)
C7—C8	1.435 (2)	C21—H21	0.9300
C8—C14	1.389 (2)	C22—C23	1.391 (2)
C8—C9	1.392 (2)	C22—C24	1.436 (2)
C9—C10	1.374 (2)	C23—H23	0.9300
C9—H9	0.9300	C24—C25	1.194 (2)
C10—C11	1.380 (2)	C25—C26	1.429 (2)
C10—H10	0.9300	C26—C27	1.379 (2)
C11—C13	1.409 (2)	C26—C30	1.384 (2)
C11—C12	1.495 (2)	C27—C28	1.370 (2)
C12—H12A	0.9600	C27—H27	0.9300
C12—H12B	0.9600	C28—C29	1.362 (3)
C12—H12C	0.9600	C28—H28	0.9300
C13—C14	1.389 (2)	C29—N4	1.331 (2)
C13—C15	1.462 (2)	C29—H29	0.9300
C14—H14	0.9300	C30—N4	1.322 (2)
C15—N2	1.2875 (19)	C30—H30	0.9300
C15—O1	1.3626 (18)	N2—N3	1.4071 (18)
C16—N3	1.2891 (19)
N1—C1—C2	124.17 (17)	C23—C17—C18	119.83 (14)
N1—C1—H1	117.9	C23—C17—C16	117.66 (13)
C2—C1—H1	117.9	C18—C17—C16	122.51 (13)
C1—C2—C3	118.65 (18)	C20—C18—C17	117.19 (15)
C1—C2—H2	120.7	C20—C18—C19	119.31 (15)
C3—C2—H2	120.7	C17—C18—C19	123.50 (15)
C2—C3—C4	119.22 (16)	C18—C19—H19A	109.5
C2—C3—H3	120.4	C18—C19—H19B	109.5
C4—C3—H3	120.4	H19A—C19—H19B	109.5
C3—C4—C5	117.04 (16)	C18—C19—H19C	109.5
C3—C4—C6	120.13 (15)	H19A—C19—H19C	109.5
C5—C4—C6	122.83 (15)	H19B—C19—H19C	109.5
N1—C5—C4	124.38 (17)	C21—C20—C18	123.08 (16)
N1—C5—H5	117.8	C21—C20—H20	118.5
C4—C5—H5	117.8	C18—C20—H20	118.5
C7—C6—C4	174.62 (18)	C20—C21—C22	119.93 (15)
C6—C7—C8	173.83 (17)	C20—C21—H21	120.0
C14—C8—C9	118.52 (15)	C22—C21—H21	120.0
C14—C8—C7	122.32 (15)	C21—C22—C23	118.45 (14)
C9—C8—C7	119.15 (15)	C21—C22—C24	120.22 (14)
C10—C9—C8	119.65 (15)	C23—C22—C24	121.33 (14)
C10—C9—H9	120.2	C22—C23—C17	121.51 (14)
C8—C9—H9	120.2	C22—C23—H23	119.2
C9—C10—C11	123.06 (15)	C17—C23—H23	119.2
C9—C10—H10	118.5	C25—C24—C22	177.27 (17)
C11—C10—H10	118.5	C24—C25—C26	177.81 (18)
C10—C11—C13	117.38 (15)	C27—C26—C30	116.94 (15)
C10—C11—C12	119.34 (15)	C27—C26—C25	123.23 (15)
C13—C11—C12	123.27 (15)	C30—C26—C25	119.83 (15)
C11—C12—H12A	109.5	C28—C27—C26	119.23 (17)
C11—C12—H12B	109.5	C28—C27—H27	120.4
H12A—C12—H12B	109.5	C26—C27—H27	120.4
C11—C12—H12C	109.5	C29—C28—C27	119.09 (18)
H12A—C12—H12C	109.5	C29—C28—H28	120.5
H12B—C12—H12C	109.5	C27—C28—H28	120.5
C14—C13—C11	119.80 (14)	N4—C29—C28	123.46 (18)
C14—C13—C15	117.99 (13)	N4—C29—H29	118.3
C11—C13—C15	122.18 (14)	C28—C29—H29	118.3
C8—C14—C13	121.49 (14)	N4—C30—C26	124.64 (17)
C8—C14—H14	119.3	N4—C30—H30	117.7
C13—C14—H14	119.3	C26—C30—H30	117.7
N2—C15—O1	111.75 (13)	C1—N1—C5	116.50 (16)
N2—C15—C13	130.81 (14)	C15—N2—N3	106.53 (13)
O1—C15—C13	117.43 (13)	C16—N3—N2	106.52 (12)
N3—C16—O1	111.69 (13)	C30—N4—C29	116.60 (17)
N3—C16—C17	130.89 (14)	C16—O1—C15	103.51 (11)
O1—C16—C17	117.42 (12)
N1—C1—C2—C3	−1.6 (3)	C16—C17—C18—C19	0.3 (2)
C1—C2—C3—C4	1.2 (3)	C17—C18—C20—C21	−1.4 (3)
C2—C3—C4—C5	0.3 (2)	C19—C18—C20—C21	178.95 (18)
C2—C3—C4—C6	−179.10 (16)	C18—C20—C21—C22	0.8 (3)
C3—C4—C5—N1	−1.5 (3)	C20—C21—C22—C23	0.1 (2)
C6—C4—C5—N1	177.82 (16)	C20—C21—C22—C24	−179.94 (16)
C14—C8—C9—C10	−2.2 (2)	C21—C22—C23—C17	−0.4 (2)
C7—C8—C9—C10	177.88 (15)	C24—C22—C23—C17	179.64 (14)
C8—C9—C10—C11	1.3 (3)	C18—C17—C23—C22	−0.2 (2)
C9—C10—C11—C13	1.4 (2)	C16—C17—C23—C22	−179.76 (13)
C9—C10—C11—C12	−177.76 (16)	C30—C26—C27—C28	2.0 (3)
C10—C11—C13—C14	−3.2 (2)	C25—C26—C27—C28	−178.01 (17)
C12—C11—C13—C14	175.94 (16)	C26—C27—C28—C29	−1.3 (3)
C10—C11—C13—C15	175.00 (14)	C27—C28—C29—N4	−0.6 (4)
C12—C11—C13—C15	−5.8 (2)	C27—C26—C30—N4	−0.8 (3)
C9—C8—C14—C13	0.4 (2)	C25—C26—C30—N4	179.15 (18)
C7—C8—C14—C13	−179.70 (15)	C2—C1—N1—C5	0.4 (3)
C11—C13—C14—C8	2.3 (2)	C4—C5—N1—C1	1.2 (3)
C15—C13—C14—C8	−175.94 (14)	O1—C15—N2—N3	0.28 (18)
C14—C13—C15—N2	−175.61 (16)	C13—C15—N2—N3	−178.60 (15)
C11—C13—C15—N2	6.2 (3)	O1—C16—N3—N2	0.30 (17)
C14—C13—C15—O1	5.6 (2)	C17—C16—N3—N2	−179.33 (15)
C11—C13—C15—O1	−172.67 (14)	C15—N2—N3—C16	−0.35 (18)
N3—C16—C17—C23	169.44 (16)	C26—C30—N4—C29	−1.0 (3)
O1—C16—C17—C23	−10.2 (2)	C28—C29—N4—C30	1.7 (3)
N3—C16—C17—C18	−10.2 (3)	N3—C16—O1—C15	−0.14 (16)
O1—C16—C17—C18	170.24 (13)	C17—C16—O1—C15	179.54 (12)
C23—C17—C18—C20	1.0 (2)	N2—C15—O1—C16	−0.10 (17)
C16—C17—C18—C20	−179.40 (15)	C13—C15—O1—C16	178.94 (13)
C23—C17—C18—C19	−179.30 (16)

(II) (2,5-Bis{2-methyl-5-[2-(pyridin-3-yl-κN)ethenyl]phenyl}-1,3,4-oxadiazole)diiodidocadmium(II) dichloromethane monosolvate

Crystal data

[CdI2(C30H20N4O)]·CH2Cl2	F(000) = 1728
Mr = 903.63	Dx = 1.870 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 5009 reflections
a = 7.039 (2) Å	θ = 2.9–24.7°
b = 15.838 (5) Å	µ = 2.80 mm^−1
c = 28.799 (9) Å	T = 298 K
V = 3210.4 (18) Å^3	Block, yellow
Z = 4	0.15 × 0.13 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3134 independent reflections
Radiation source: fine-focus sealed tube	2357 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
phi and ω scans	θmax = 25.6°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −8→5
Tmin = 0.679, Tmax = 0.730	k = −18→19
16042 measured reflections	l = −35→34

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.159	H-atom parameters constrained
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0856P)^2 + 2.7184P] where P = (Fo^2 + 2Fc^2)/3
3134 reflections	(Δ/σ)max = 0.001
197 parameters	Δρmax = 2.12 e Å^−3
0 restraints	Δρmin = −1.15 e Å^−3

Special details

Experimental. IR (v, cm^-1): 2977 (w), 2921 (w), 2225 (w),1593 (m), 1536 (m), 1499 (m),1477 (m), 1414 (m), 1379 (w), 1275 (w), 1237 (w), 1150 (w), 1055 (m), 895 (m), 831 (m), 801 (s), 751 (w), 723 (s), 690 (vs), 644 (m), 575 (m).

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	Occ. (<1)
C1	0.2517 (10)	0.0739 (5)	0.5905 (2)	0.0562 (17)
H1	0.2675	0.0859	0.6218	0.067*
C2	0.3083 (11)	−0.0045 (5)	0.5743 (2)	0.0582 (17)
H2	0.3550	−0.0452	0.5946	0.070*
C3	0.2939 (10)	−0.0208 (4)	0.5278 (2)	0.0526 (16)
H3	0.3311	−0.0730	0.5161	0.063*
C4	0.2235 (8)	0.0409 (4)	0.49796 (19)	0.0435 (14)
C5	0.1629 (9)	0.1166 (4)	0.5177 (2)	0.0490 (15)
H5	0.1111	0.1577	0.4984	0.059*
C6	0.2111 (9)	0.0297 (4)	0.4484 (2)	0.0475 (15)
C7	0.2075 (9)	0.0233 (4)	0.4073 (2)	0.0455 (14)
C8	0.2127 (9)	0.0216 (4)	0.35779 (19)	0.0438 (14)
C9	0.2235 (10)	−0.0537 (4)	0.3325 (2)	0.0532 (16)
H9	0.2304	−0.1052	0.3480	0.064*
C10	0.2240 (10)	−0.0517 (4)	0.2851 (2)	0.0544 (16)
H10	0.2294	−0.1024	0.2689	0.065*
C11	0.2166 (8)	0.0241 (4)	0.26002 (19)	0.0424 (13)
C12	0.2173 (10)	0.0205 (4)	0.2082 (2)	0.0512 (16)
H12A	0.3315	0.0461	0.1966	0.077*
H12B	0.1089	0.0503	0.1963	0.077*
H12C	0.2120	−0.0374	0.1983	0.077*
C13	0.2088 (8)	0.0998 (4)	0.28546 (19)	0.0397 (12)
C14	0.2048 (8)	0.0972 (4)	0.3339 (2)	0.0428 (13)
H14	0.1967	0.1475	0.3505	0.051*
C15	0.2043 (8)	0.1833 (4)	0.26380 (19)	0.0416 (13)
C16	0.690 (6)	0.2500	0.3865 (5)	0.224 (18)
H16A	0.6827	0.2007	0.3666	0.269*	0.50
H16B	0.6827	0.2993	0.3666	0.269*	0.50
Cd1	0.04179 (12)	0.2500	0.59622 (2)	0.0575 (3)
Cl1	0.4954 (10)	0.2500	0.4212 (3)	0.173 (2)
Cl2	0.8989 (13)	0.2500	0.4121 (2)	0.212 (4)
I1	0.14777 (16)	0.2500	0.68577 (2)	0.0867 (4)
I2	−0.31148 (13)	0.2500	0.55923 (3)	0.0815 (3)
N1	0.1758 (8)	0.1330 (3)	0.56335 (16)	0.0490 (12)
N2	0.1996 (9)	0.2053 (4)	0.22098 (18)	0.0595 (15)
O1	0.2067 (8)	0.2500	0.29210 (17)	0.0411 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.072 (5)	0.066 (4)	0.030 (3)	0.002 (4)	−0.006 (3)	0.007 (3)
C2	0.071 (5)	0.062 (4)	0.041 (3)	0.013 (4)	0.001 (3)	0.013 (3)
C3	0.059 (4)	0.050 (4)	0.049 (4)	0.007 (3)	0.006 (3)	0.006 (3)
C4	0.045 (3)	0.050 (3)	0.036 (3)	−0.004 (3)	0.001 (2)	0.000 (3)
C5	0.061 (4)	0.050 (4)	0.036 (3)	0.006 (3)	−0.004 (3)	0.007 (3)
C6	0.053 (4)	0.050 (4)	0.039 (3)	0.004 (3)	0.004 (3)	0.002 (3)
C7	0.054 (4)	0.042 (3)	0.041 (3)	−0.001 (3)	0.003 (3)	0.000 (3)
C8	0.048 (3)	0.048 (3)	0.036 (3)	−0.003 (3)	0.001 (2)	−0.004 (2)
C9	0.072 (4)	0.043 (3)	0.045 (3)	−0.003 (3)	0.003 (3)	−0.001 (3)
C10	0.069 (4)	0.046 (4)	0.049 (3)	−0.002 (3)	0.006 (3)	−0.015 (3)
C11	0.044 (3)	0.049 (3)	0.034 (3)	−0.003 (3)	0.003 (3)	−0.009 (2)
C12	0.058 (4)	0.060 (4)	0.036 (3)	−0.003 (3)	0.002 (3)	−0.009 (3)
C13	0.039 (3)	0.045 (3)	0.035 (3)	−0.001 (2)	0.003 (2)	−0.004 (2)
C14	0.048 (3)	0.046 (3)	0.035 (3)	−0.003 (3)	0.003 (2)	−0.009 (3)
C15	0.039 (3)	0.050 (3)	0.035 (3)	−0.002 (3)	0.000 (2)	−0.007 (2)
C16	0.48 (6)	0.146 (19)	0.041 (8)	0.000	−0.040 (18)	0.000
Cd1	0.0885 (6)	0.0478 (4)	0.0362 (4)	0.000	0.0013 (3)	0.000
Cl1	0.158 (5)	0.215 (7)	0.146 (5)	0.000	−0.044 (4)	0.000
Cl2	0.202 (7)	0.310 (11)	0.125 (5)	0.000	0.056 (5)	0.000
I1	0.1671 (10)	0.0555 (4)	0.0375 (4)	0.000	−0.0139 (4)	0.000
I2	0.0817 (6)	0.0707 (5)	0.0922 (6)	0.000	−0.0070 (4)	0.000
N1	0.064 (3)	0.049 (3)	0.033 (2)	−0.002 (2)	−0.003 (2)	−0.001 (2)
N2	0.090 (4)	0.052 (3)	0.037 (3)	0.001 (3)	−0.002 (3)	0.000 (2)
O1	0.055 (3)	0.041 (3)	0.027 (3)	0.000	0.000 (2)	0.000

Geometric parameters (Å, º)

C1—N1	1.330 (8)	C11—C12	1.494 (8)
C1—C2	1.386 (10)	C12—H12A	0.9600
C1—H1	0.9300	C12—H12B	0.9600
C2—C3	1.368 (10)	C12—H12C	0.9600
C2—H2	0.9300	C13—C14	1.396 (8)
C3—C4	1.392 (9)	C13—C15	1.463 (8)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.393 (9)	C15—N2	1.282 (8)
C4—C6	1.440 (8)	C15—O1	1.334 (6)
C5—N1	1.344 (8)	C16—Cl2	1.65 (3)
C5—H5	0.9300	C16—Cl1	1.69 (3)
C6—C7	1.189 (8)	C16—H16A	0.9700
C7—C8	1.427 (8)	C16—H16B	0.9700
C8—C14	1.383 (9)	Cd1—N1	2.285 (5)
C8—C9	1.400 (9)	Cd1—N1^i	2.285 (5)
C9—C10	1.364 (9)	Cd1—I1	2.6845 (12)
C9—H9	0.9300	Cd1—I2	2.7053 (14)
C10—C11	1.402 (9)	N2—N2^i	1.415 (11)
C10—H10	0.9300	O1—C15^i	1.334 (6)
C11—C13	1.406 (8)
N1—C1—C2	123.3 (6)	H12A—C12—H12B	109.5
N1—C1—H1	118.4	C11—C12—H12C	109.5
C2—C1—H1	118.4	H12A—C12—H12C	109.5
C3—C2—C1	118.4 (6)	H12B—C12—H12C	109.5
C3—C2—H2	120.8	C14—C13—C11	119.8 (5)
C1—C2—H2	120.8	C14—C13—C15	116.9 (5)
C2—C3—C4	119.9 (6)	C11—C13—C15	123.3 (5)
C2—C3—H3	120.0	C8—C14—C13	121.5 (5)
C4—C3—H3	120.0	C8—C14—H14	119.3
C3—C4—C5	117.5 (5)	C13—C14—H14	119.3
C3—C4—C6	123.1 (6)	N2—C15—O1	111.9 (6)
C5—C4—C6	119.4 (6)	N2—C15—C13	131.0 (5)
N1—C5—C4	123.0 (6)	O1—C15—C13	117.1 (5)
N1—C5—H5	118.5	Cl2—C16—Cl1	117.3 (9)
C4—C5—H5	118.5	Cl2—C16—H16A	108.0
C7—C6—C4	176.8 (7)	Cl1—C16—H16A	108.0
C6—C7—C8	175.4 (7)	Cl2—C16—H16B	108.0
C14—C8—C9	118.8 (5)	Cl1—C16—H16B	108.0
C14—C8—C7	118.7 (5)	H16A—C16—H16B	107.2
C9—C8—C7	122.6 (6)	N1—Cd1—N1^i	108.4 (3)
C10—C9—C8	120.0 (6)	N1—Cd1—I1	106.45 (12)
C10—C9—H9	120.0	N1^i—Cd1—I1	106.45 (12)
C8—C9—H9	120.0	N1—Cd1—I2	102.49 (13)
C9—C10—C11	122.4 (6)	N1^i—Cd1—I2	102.49 (13)
C9—C10—H10	118.8	I1—Cd1—I2	129.33 (4)
C11—C10—H10	118.8	C1—N1—C5	117.8 (6)
C10—C11—C13	117.6 (5)	C1—N1—Cd1	119.5 (4)
C10—C11—C12	118.8 (6)	C5—N1—Cd1	122.3 (4)
C13—C11—C12	123.6 (6)	C15—N2—N2^i	105.8 (4)
C11—C12—H12A	109.5	C15—O1—C15^i	104.7 (6)
C11—C12—H12B	109.5
N1—C1—C2—C3	3.2 (12)	C14—C13—C15—N2	−177.2 (6)
C1—C2—C3—C4	0.0 (11)	C11—C13—C15—N2	2.8 (10)
C2—C3—C4—C5	−2.6 (10)	C14—C13—C15—O1	3.4 (8)
C2—C3—C4—C6	177.5 (7)	C11—C13—C15—O1	−176.7 (6)
C3—C4—C5—N1	2.4 (10)	C2—C1—N1—C5	−3.4 (11)
C6—C4—C5—N1	−177.7 (6)	C2—C1—N1—Cd1	169.4 (6)
C14—C8—C9—C10	−0.8 (10)	C4—C5—N1—C1	0.6 (10)
C7—C8—C9—C10	178.6 (6)	C4—C5—N1—Cd1	−172.1 (5)
C8—C9—C10—C11	0.9 (10)	N1^i—Cd1—N1—C1	126.6 (5)
C9—C10—C11—C13	0.1 (10)	I1—Cd1—N1—C1	12.4 (5)
C9—C10—C11—C12	−179.9 (6)	I2—Cd1—N1—C1	−125.5 (5)
C10—C11—C13—C14	−1.3 (8)	N1^i—Cd1—N1—C5	−60.9 (6)
C12—C11—C13—C14	178.7 (6)	I1—Cd1—N1—C5	−175.1 (5)
C10—C11—C13—C15	178.8 (6)	I2—Cd1—N1—C5	47.0 (5)
C12—C11—C13—C15	−1.3 (9)	O1—C15—N2—N2^i	0.2 (6)
C9—C8—C14—C13	−0.4 (9)	C13—C15—N2—N2^i	−179.2 (6)
C7—C8—C14—C13	−179.8 (6)	N2—C15—O1—C15^i	−0.4 (9)
C11—C13—C14—C8	1.4 (9)	C13—C15—O1—C15^i	179.2 (3)
C15—C13—C14—C8	−178.6 (5)

Symmetry code: (i) x, −y+1/2, z.

(III) Di-µ-iodido-bis[(2,5-bis{2-methyl-5-[2-(pyridin-3-yl-κN)ethenyl]phenyl}-1,3,4-oxadiazole)copper(I)]

Crystal data

[Cu2I2(C30H20N4O)2]	Z = 1
Mr = 1285.88	F(000) = 636
Triclinic, P1	Dx = 1.646 Mg m^−3
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4320 (15) Å	Cell parameters from 3357 reflections
b = 10.5080 (18) Å	θ = 2.4–27.9°
c = 14.238 (2) Å	µ = 2.06 mm^−1
α = 88.717 (2)°	T = 298 K
β = 85.154 (2)°	Block, yellow
γ = 67.344 (2)°	0.35 × 0.22 × 0.10 mm
V = 1297.5 (4) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	4803 independent reflections
Radiation source: fine-focus sealed tube	4132 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
phi and ω scans	θmax = 25.6°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −10→11
Tmin = 0.532, Tmax = 0.820	k = −5→12
6918 measured reflections	l = −17→17

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0511P)^2] where P = (Fo^2 + 2Fc^2)/3
4803 reflections	(Δ/σ)max = 0.001
336 parameters	Δρmax = 0.79 e Å^−3
0 restraints	Δρmin = −0.54 e Å^−3

Special details

Experimental. IR (v, cm^-1): 2962 (w), 2911 (w), 2315 (w), 1537 (m), 1502 (w), 1471 (w), 1441 (w), 1403 (m), 1280 (w), 1234 (w), 1149 (w), 1098 (m), 1028 (w), 994 (w), 959 (w), 898 (w), 830 (s), 804 (s), 748 (m), 695 (vs), 640 (w), 572(m).

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	1.2760 (4)	0.1287 (4)	0.4338 (3)	0.0491 (9)
H1	1.2771	0.1327	0.4990	0.059*
C2	1.3889 (5)	0.0201 (4)	0.3853 (3)	0.0527 (10)
H2	1.4658	−0.0462	0.4168	0.063*
C3	1.3861 (4)	0.0114 (4)	0.2892 (3)	0.0465 (9)
H3	1.4603	−0.0620	0.2550	0.056*
C4	1.2722 (4)	0.1126 (4)	0.2441 (2)	0.0404 (8)
C5	1.1647 (4)	0.2215 (4)	0.2992 (2)	0.0410 (8)
H5	1.0898	0.2920	0.2692	0.049*
C6	1.2558 (4)	0.1074 (4)	0.1455 (3)	0.0428 (9)
C7	1.2350 (4)	0.0998 (4)	0.0652 (3)	0.0425 (9)
C8	1.1920 (4)	0.0889 (4)	−0.0281 (2)	0.0409 (8)
C9	1.3001 (4)	0.0182 (4)	−0.1017 (3)	0.0482 (9)
H9	1.4049	−0.0177	−0.0931	0.058*
C10	1.2491 (4)	0.0023 (4)	−0.1874 (3)	0.0504 (10)
H10	1.3219	−0.0463	−0.2354	0.061*
C11	1.0954 (4)	0.0551 (4)	−0.2052 (2)	0.0420 (8)
C12	1.0509 (5)	0.0303 (4)	−0.3002 (2)	0.0517 (10)
H12A	0.9713	−0.0056	−0.2919	0.078*
H12B	1.1393	−0.0348	−0.3356	0.078*
H12C	1.0138	0.1157	−0.3338	0.078*
C13	0.9875 (4)	0.1294 (4)	−0.1320 (2)	0.0381 (8)
C14	1.0388 (4)	0.1439 (4)	−0.0451 (2)	0.0397 (8)
H14	0.9665	0.1926	0.0030	0.048*
C15	0.8218 (4)	0.1905 (4)	−0.1410 (2)	0.0394 (8)
C16	0.5857 (4)	0.2893 (4)	−0.0880 (2)	0.0360 (8)
C17	0.4608 (4)	0.3491 (4)	−0.0132 (2)	0.0360 (8)
C18	0.3068 (4)	0.4221 (4)	−0.0320 (2)	0.0428 (9)
C19	0.2546 (5)	0.4437 (6)	−0.1298 (3)	0.0664 (13)
H19A	0.2521	0.3596	−0.1531	0.100*
H19B	0.3251	0.4701	−0.1704	0.100*
H19C	0.1534	0.5152	−0.1287	0.100*
C20	0.2012 (4)	0.4780 (4)	0.0453 (3)	0.0447 (9)
H20	0.0986	0.5276	0.0346	0.054*
C21	0.2417 (4)	0.4632 (4)	0.1363 (2)	0.0417 (8)
H21	0.1671	0.5023	0.1857	0.050*
C22	0.3940 (4)	0.3900 (4)	0.1549 (2)	0.0361 (8)
C23	0.5026 (4)	0.3349 (4)	0.0785 (2)	0.0370 (8)
H23	0.6056	0.2876	0.0895	0.044*
C24	0.4471 (4)	0.3726 (4)	0.2475 (2)	0.0406 (8)
C25	0.5023 (4)	0.3541 (4)	0.3214 (2)	0.0392 (8)
C26	0.5740 (4)	0.3402 (4)	0.4079 (2)	0.0369 (8)
C27	0.5033 (4)	0.3267 (4)	0.4955 (2)	0.0406 (8)
H27	0.4062	0.3225	0.5004	0.049*
C28	0.5804 (4)	0.3197 (4)	0.5744 (2)	0.0450 (9)
H28	0.5359	0.3101	0.6335	0.054*
C29	0.7232 (4)	0.3270 (4)	0.5659 (2)	0.0415 (8)
H29	0.7737	0.3214	0.6201	0.050*
C30	0.7191 (4)	0.3466 (4)	0.4062 (2)	0.0404 (8)
H30	0.7673	0.3547	0.3479	0.049*
Cu1	0.99071 (5)	0.38362 (5)	0.47112 (3)	0.04721 (14)
I1	0.91337 (3)	0.60761 (3)	0.362610 (15)	0.04455 (10)
N1	1.1646 (3)	0.2289 (3)	0.39230 (19)	0.0413 (7)
N2	0.7414 (3)	0.2146 (3)	−0.21275 (19)	0.0460 (8)
N3	0.5858 (3)	0.2785 (3)	−0.17785 (19)	0.0453 (8)
N4	0.7928 (3)	0.3418 (3)	0.48270 (19)	0.0400 (7)
O1	0.7310 (3)	0.2355 (3)	−0.05887 (15)	0.0397 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.056 (2)	0.058 (3)	0.037 (2)	−0.023 (2)	−0.0148 (17)	0.0008 (19)
C2	0.056 (2)	0.047 (2)	0.053 (2)	−0.014 (2)	−0.0218 (19)	0.0019 (19)
C3	0.046 (2)	0.043 (2)	0.047 (2)	−0.0122 (18)	−0.0116 (17)	−0.0057 (18)
C4	0.041 (2)	0.049 (2)	0.0360 (19)	−0.0218 (18)	−0.0040 (15)	−0.0021 (17)
C5	0.0369 (19)	0.052 (2)	0.0345 (18)	−0.0170 (18)	−0.0064 (14)	0.0031 (17)
C6	0.0352 (19)	0.048 (2)	0.043 (2)	−0.0145 (17)	−0.0030 (15)	−0.0013 (18)
C7	0.0349 (19)	0.049 (2)	0.040 (2)	−0.0118 (17)	−0.0026 (15)	0.0002 (17)
C8	0.044 (2)	0.043 (2)	0.0345 (19)	−0.0145 (17)	−0.0028 (15)	−0.0001 (16)
C9	0.037 (2)	0.056 (2)	0.044 (2)	−0.0110 (19)	0.0008 (16)	−0.0025 (19)
C10	0.046 (2)	0.059 (3)	0.036 (2)	−0.012 (2)	0.0096 (16)	−0.0084 (18)
C11	0.049 (2)	0.043 (2)	0.0321 (18)	−0.0168 (18)	0.0043 (16)	−0.0043 (16)
C12	0.057 (2)	0.061 (3)	0.035 (2)	−0.021 (2)	0.0024 (17)	−0.0115 (19)
C13	0.0418 (19)	0.039 (2)	0.0304 (17)	−0.0129 (16)	−0.0005 (14)	0.0007 (15)
C14	0.0389 (19)	0.045 (2)	0.0297 (17)	−0.0103 (17)	0.0002 (14)	−0.0032 (16)
C15	0.044 (2)	0.047 (2)	0.0238 (17)	−0.0148 (18)	0.0012 (14)	−0.0043 (15)
C16	0.0343 (18)	0.042 (2)	0.0315 (17)	−0.0131 (16)	−0.0093 (14)	0.0016 (15)
C17	0.0354 (18)	0.044 (2)	0.0286 (17)	−0.0151 (16)	−0.0043 (13)	−0.0021 (15)
C18	0.042 (2)	0.055 (2)	0.0348 (19)	−0.0201 (18)	−0.0136 (15)	0.0047 (17)
C19	0.051 (2)	0.105 (4)	0.038 (2)	−0.022 (3)	−0.0168 (18)	0.007 (2)
C20	0.0310 (18)	0.056 (2)	0.046 (2)	−0.0148 (17)	−0.0058 (15)	−0.0031 (18)
C21	0.0344 (18)	0.054 (2)	0.0376 (19)	−0.0185 (18)	0.0001 (15)	−0.0056 (17)
C22	0.0387 (19)	0.046 (2)	0.0284 (17)	−0.0212 (17)	−0.0027 (14)	−0.0045 (15)
C23	0.0321 (17)	0.048 (2)	0.0305 (17)	−0.0139 (16)	−0.0064 (13)	0.0007 (16)
C24	0.0382 (19)	0.056 (2)	0.0305 (18)	−0.0209 (18)	−0.0009 (15)	−0.0046 (17)
C25	0.0374 (19)	0.050 (2)	0.0322 (18)	−0.0185 (17)	−0.0029 (15)	−0.0047 (16)
C26	0.0383 (19)	0.043 (2)	0.0309 (17)	−0.0170 (16)	−0.0061 (14)	−0.0024 (15)
C27	0.0409 (19)	0.048 (2)	0.0364 (19)	−0.0215 (18)	−0.0028 (15)	−0.0030 (17)
C28	0.056 (2)	0.057 (2)	0.0278 (18)	−0.028 (2)	−0.0021 (16)	0.0053 (17)
C29	0.047 (2)	0.047 (2)	0.0305 (18)	−0.0171 (18)	−0.0116 (15)	0.0037 (16)
C30	0.0390 (19)	0.055 (2)	0.0281 (17)	−0.0188 (18)	−0.0014 (14)	−0.0028 (16)
Cu1	0.0411 (3)	0.0668 (3)	0.0349 (2)	−0.0212 (2)	−0.00661 (19)	−0.0040 (2)
I1	0.04870 (16)	0.06131 (19)	0.02704 (14)	−0.02383 (13)	−0.00866 (10)	0.00147 (11)
N1	0.0408 (16)	0.0508 (19)	0.0330 (16)	−0.0174 (15)	−0.0068 (12)	−0.0016 (14)
N2	0.0468 (18)	0.061 (2)	0.0269 (15)	−0.0174 (16)	−0.0034 (13)	−0.0042 (14)
N3	0.0446 (17)	0.061 (2)	0.0266 (15)	−0.0148 (16)	−0.0064 (12)	−0.0028 (14)
N4	0.0379 (15)	0.0551 (19)	0.0282 (14)	−0.0183 (15)	−0.0057 (12)	−0.0022 (14)
O1	0.0381 (13)	0.0526 (15)	0.0246 (11)	−0.0131 (12)	−0.0034 (9)	−0.0025 (11)

Geometric parameters (Å, º)

C1—N1	1.336 (5)	C17—C18	1.403 (5)
C1—C2	1.374 (5)	C18—C20	1.392 (5)
C1—H1	0.9300	C18—C19	1.501 (5)
C2—C3	1.377 (5)	C19—H19A	0.9600
C2—H2	0.9300	C19—H19B	0.9600
C3—C4	1.379 (5)	C19—H19C	0.9600
C3—H3	0.9300	C20—C21	1.370 (5)
C4—C5	1.401 (5)	C20—H20	0.9300
C4—C6	1.430 (5)	C21—C22	1.389 (5)
C5—N1	1.329 (4)	C21—H21	0.9300
C5—H5	0.9300	C22—C23	1.398 (4)
C6—C7	1.187 (5)	C22—C24	1.432 (5)
C7—C8	1.441 (5)	C23—H23	0.9300
C8—C14	1.375 (5)	C24—C25	1.192 (5)
C8—C9	1.400 (5)	C25—C26	1.433 (5)
C9—C10	1.385 (5)	C26—C30	1.394 (5)
C9—H9	0.9300	C26—C27	1.394 (5)
C10—C11	1.381 (5)	C27—C28	1.375 (5)
C10—H10	0.9300	C27—H27	0.9300
C11—C13	1.406 (5)	C28—C29	1.373 (5)
C11—C12	1.507 (5)	C28—H28	0.9300
C12—H12A	0.9600	C29—N4	1.341 (4)
C12—H12B	0.9600	C29—H29	0.9300
C12—H12C	0.9600	C30—N4	1.331 (4)
C13—C14	1.397 (5)	C30—H30	0.9300
C13—C15	1.459 (5)	Cu1—N4	2.069 (3)
C14—H14	0.9300	Cu1—N1	2.076 (3)
C15—N2	1.286 (4)	Cu1—I1^i	2.6206 (6)
C15—O1	1.367 (4)	Cu1—Cu1^i	2.6710 (10)
C16—N3	1.287 (4)	Cu1—I1	2.6765 (7)
C16—O1	1.363 (4)	I1—Cu1^i	2.6206 (6)
C16—C17	1.471 (5)	N2—N3	1.409 (4)
C17—C23	1.384 (4)
N1—C1—C2	123.4 (3)	C18—C19—H19B	109.5
N1—C1—H1	118.3	H19A—C19—H19B	109.5
C2—C1—H1	118.3	C18—C19—H19C	109.5
C1—C2—C3	118.8 (4)	H19A—C19—H19C	109.5
C1—C2—H2	120.6	H19B—C19—H19C	109.5
C3—C2—H2	120.6	C21—C20—C18	123.0 (3)
C2—C3—C4	119.3 (3)	C21—C20—H20	118.5
C2—C3—H3	120.3	C18—C20—H20	118.5
C4—C3—H3	120.3	C20—C21—C22	120.1 (3)
C3—C4—C5	117.8 (3)	C20—C21—H21	119.9
C3—C4—C6	122.9 (3)	C22—C21—H21	119.9
C5—C4—C6	119.3 (3)	C21—C22—C23	118.0 (3)
N1—C5—C4	123.2 (3)	C21—C22—C24	123.8 (3)
N1—C5—H5	118.4	C23—C22—C24	118.2 (3)
C4—C5—H5	118.4	C17—C23—C22	121.6 (3)
C7—C6—C4	175.7 (4)	C17—C23—H23	119.2
C6—C7—C8	172.8 (4)	C22—C23—H23	119.2
C14—C8—C9	118.3 (3)	C25—C24—C22	175.0 (4)
C14—C8—C7	119.3 (3)	C24—C25—C26	175.2 (4)
C9—C8—C7	122.4 (3)	C30—C26—C27	117.5 (3)
C10—C9—C8	119.2 (3)	C30—C26—C25	119.0 (3)
C10—C9—H9	120.4	C27—C26—C25	123.4 (3)
C8—C9—H9	120.4	C28—C27—C26	118.4 (3)
C11—C10—C9	123.3 (3)	C28—C27—H27	120.8
C11—C10—H10	118.4	C26—C27—H27	120.8
C9—C10—H10	118.4	C29—C28—C27	120.0 (3)
C10—C11—C13	117.4 (3)	C29—C28—H28	120.0
C10—C11—C12	119.4 (3)	C27—C28—H28	120.0
C13—C11—C12	123.2 (3)	N4—C29—C28	122.8 (3)
C11—C12—H12A	109.5	N4—C29—H29	118.6
C11—C12—H12B	109.5	C28—C29—H29	118.6
H12A—C12—H12B	109.5	N4—C30—C26	124.0 (3)
C11—C12—H12C	109.5	N4—C30—H30	118.0
H12A—C12—H12C	109.5	C26—C30—H30	118.0
H12B—C12—H12C	109.5	N4—Cu1—N1	109.55 (11)
C14—C13—C11	119.3 (3)	N4—Cu1—I1^i	110.98 (8)
C14—C13—C15	117.5 (3)	N1—Cu1—I1^i	107.95 (8)
C11—C13—C15	123.2 (3)	N4—Cu1—Cu1^i	125.14 (9)
C8—C14—C13	122.5 (3)	N1—Cu1—Cu1^i	124.87 (8)
C8—C14—H14	118.7	I1^i—Cu1—Cu1^i	60.760 (17)
C13—C14—H14	118.7	N4—Cu1—I1	102.93 (9)
N2—C15—O1	111.8 (3)	N1—Cu1—I1	105.59 (9)
N2—C15—C13	132.5 (3)	I1^i—Cu1—I1	119.45 (2)
O1—C15—C13	115.8 (3)	Cu1^i—Cu1—I1	58.69 (2)
N3—C16—O1	112.1 (3)	Cu1^i—I1—Cu1	60.55 (2)
N3—C16—C17	132.4 (3)	C5—N1—C1	117.5 (3)
O1—C16—C17	115.6 (3)	C5—N1—Cu1	121.3 (2)
C23—C17—C18	120.4 (3)	C1—N1—Cu1	121.1 (2)
C23—C17—C16	116.7 (3)	C15—N2—N3	106.6 (3)
C18—C17—C16	122.9 (3)	C16—N3—N2	106.3 (3)
C20—C18—C17	116.9 (3)	C30—N4—C29	117.2 (3)
C20—C18—C19	120.1 (3)	C30—N4—Cu1	119.4 (2)
C17—C18—C19	122.9 (3)	C29—N4—Cu1	122.8 (2)
C18—C19—H19A	109.5	C16—O1—C15	103.2 (3)
N1—C1—C2—C3	−1.6 (6)	C25—C26—C27—C28	−177.4 (4)
C1—C2—C3—C4	1.1 (6)	C26—C27—C28—C29	0.4 (6)
C2—C3—C4—C5	0.7 (5)	C27—C28—C29—N4	0.5 (6)
C2—C3—C4—C6	−176.4 (4)	C27—C26—C30—N4	−0.6 (6)
C3—C4—C5—N1	−2.4 (5)	C25—C26—C30—N4	176.5 (4)
C6—C4—C5—N1	174.9 (3)	N4—Cu1—I1—Cu1^i	123.47 (8)
C14—C8—C9—C10	−2.1 (6)	N1—Cu1—I1—Cu1^i	−121.67 (8)
C7—C8—C9—C10	174.8 (4)	I1^i—Cu1—I1—Cu1^i	0.0
C8—C9—C10—C11	1.1 (7)	C4—C5—N1—C1	1.9 (5)
C9—C10—C11—C13	0.6 (6)	C4—C5—N1—Cu1	−174.4 (3)
C9—C10—C11—C12	−179.0 (4)	C2—C1—N1—C5	0.1 (6)
C10—C11—C13—C14	−1.4 (6)	C2—C1—N1—Cu1	176.5 (3)
C12—C11—C13—C14	178.1 (4)	N4—Cu1—N1—C5	75.1 (3)
C10—C11—C13—C15	−179.9 (4)	I1^i—Cu1—N1—C5	−163.9 (2)
C12—C11—C13—C15	−0.4 (6)	Cu1^i—Cu1—N1—C5	−97.5 (3)
C9—C8—C14—C13	1.3 (6)	I1—Cu1—N1—C5	−35.1 (3)
C7—C8—C14—C13	−175.6 (3)	N4—Cu1—N1—C1	−101.1 (3)
C11—C13—C14—C8	0.5 (6)	I1^i—Cu1—N1—C1	19.8 (3)
C15—C13—C14—C8	179.1 (3)	Cu1^i—Cu1—N1—C1	86.2 (3)
C14—C13—C15—N2	167.1 (4)	I1—Cu1—N1—C1	148.7 (3)
C11—C13—C15—N2	−14.4 (7)	O1—C15—N2—N3	−0.7 (4)
C14—C13—C15—O1	−10.9 (5)	C13—C15—N2—N3	−178.7 (4)
C11—C13—C15—O1	167.7 (3)	O1—C16—N3—N2	−0.8 (4)
N3—C16—C17—C23	176.0 (4)	C17—C16—N3—N2	178.4 (4)
O1—C16—C17—C23	−4.8 (5)	C15—N2—N3—C16	0.9 (4)
N3—C16—C17—C18	−6.4 (6)	C26—C30—N4—C29	1.4 (6)
O1—C16—C17—C18	172.8 (3)	C26—C30—N4—Cu1	−170.3 (3)
C23—C17—C18—C20	0.0 (6)	C28—C29—N4—C30	−1.4 (5)
C16—C17—C18—C20	−177.5 (3)	C28—C29—N4—Cu1	170.1 (3)
C23—C17—C18—C19	178.7 (4)	N1—Cu1—N4—C30	−67.3 (3)
C16—C17—C18—C19	1.2 (6)	I1^i—Cu1—N4—C30	173.5 (3)
C17—C18—C20—C21	−0.6 (6)	Cu1^i—Cu1—N4—C30	105.3 (3)
C19—C18—C20—C21	−179.3 (4)	I1—Cu1—N4—C30	44.6 (3)
C18—C20—C21—C22	0.1 (6)	N1—Cu1—N4—C29	121.4 (3)
C20—C21—C22—C23	0.9 (5)	I1^i—Cu1—N4—C29	2.3 (3)
C20—C21—C22—C24	178.3 (3)	Cu1^i—Cu1—N4—C29	−66.0 (3)
C18—C17—C23—C22	1.1 (5)	I1—Cu1—N4—C29	−126.6 (3)
C16—C17—C23—C22	178.7 (3)	N3—C16—O1—C15	0.4 (4)
C21—C22—C23—C17	−1.6 (5)	C17—C16—O1—C15	−179.0 (3)
C24—C22—C23—C17	−179.1 (3)	N2—C15—O1—C16	0.2 (4)
C30—C26—C27—C28	−0.3 (5)	C13—C15—O1—C16	178.6 (3)

Symmetry code: (i) −x+2, −y+1, −z+1.