One-dimensional networks formed via the self-assembly of anthracenedi­benzoic acid with zinc(II)

Self-assembly of metal–organic coordination polymers occurs because of enthalpically favorable inter­actions. In the case of the bulky 4,4′-(anthracene-9,10-di­yl)di­benzoic acid ligand (abdH₂), we demonstrate that the presence of numerous π–π and C—H...π inter­actions outweigh the formation of saturated coordination complexes with zinc, leading to the formation of a di­methyl­formamide (DMF) solvate, namely 4,4′-(anthracene-9,10-di­yl)di­benzoic acid di­methyl­formamide disolvate, C₂₈H₁₈O₄·2C₃H₇NO or [(abdH₂)(DMF)₂], at low concentrations of zinc. Meanwhile, at higher zinc concentrations, the abdH₂ ligand gives rise to the nonporous one-dimensional coordination polymer catena-poly[[bis­(di­methyl­formamide-κO)zinc(II)]-μ-4,4′-(anthracene-9,10-di­yl)di­ben­zoato-κ²O:O′], [Zn(C₂₈H₁₆O₄)(C₃H₇NO)₂]_n or [Zn(abd)(DMF)₂]_n, when assembled in di­methyl­formamide, while a related compound is observed when N,N-di­methyl­acetamide (DMA) is used as the solvent, namely catena-poly[[[bis­(N,N-di­methyl­acetamide-κO)zinc(II)]-μ-4,4′-(anthracene-9,10-di­yl)di­benzoato-κ²O:O′] N,N-di­methyl­acetamide monosolvate], {[Zn(C₂₈H₁₆O₄)(C₄H₉NO)₂]·C₄H₉NO}_n or {[Zn(abd)(DMA)₂]·DMA}_n. Attempts to use other amide-based solvents did not give rise to any other assembled structures.

Computing details

For all structures, data collection: APEX3 (Bruker, 2017); cell refinement: SAINT (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

4,4'-(Anthracene-9,10-diyl)dibenzoic acid dimethylformamide disolvate (abd_H2DMF2)

Crystal data

C28H18O4·2C3H7NO	Z = 1
Mr = 564.61	F(000) = 298
Triclinic, P1	Dx = 1.318 Mg m^−3
a = 7.199 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.931 (2) Å	Cell parameters from 4997 reflections
c = 12.221 (2) Å	θ = 1.8–33.0°
α = 70.46 (3)°	µ = 0.09 mm^−1
β = 76.74 (3)°	T = 130 K
γ = 76.97 (3)°	Plate-like, yellow
V = 711.2 (3) Å^3	0.20 × 0.12 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer	3582 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
ω and phi scans	θmax = 33.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −10→10
Tmin = 0.685, Tmax = 0.747	k = −13→13
12550 measured reflections	l = −18→18
4997 independent reflections

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.149	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.071P)^2 + 0.3013P] where P = (Fo^2 + 2Fc^2)/3
4997 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.39 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	Occ. (<1)
N1	−0.18624 (15)	0.11290 (14)	0.57982 (10)	0.0195 (2)
O2A	0.29443 (16)	0.41552 (15)	0.43168 (9)	0.0350 (3)	0.546 (3)
O1A	0.15176 (15)	0.48055 (14)	0.27410 (9)	0.0313 (3)	0.546 (3)
H11A	0.0798	0.4198	0.3208	0.038*	0.546 (3)
O1B	0.15176 (15)	0.48055 (14)	0.27410 (9)	0.0313 (3)	0.454 (3)
O2B	0.29443 (16)	0.41552 (15)	0.43168 (9)	0.0350 (3)	0.454 (3)
H11B	0.2072	0.3615	0.4610	0.042*	0.454 (3)
C15A	−0.07498 (19)	0.22073 (17)	0.51327 (12)	0.0211 (3)	0.546 (3)
H15A	0.0128	0.2474	0.5461	0.025*	0.546 (3)
C15B	−0.07498 (19)	0.22073 (17)	0.51327 (12)	0.0211 (3)	0.454 (3)
H15B	−0.0974	0.2854	0.4386	0.025*	0.454 (3)
O3B	0.0639 (3)	0.2309 (3)	0.5570 (2)	0.0279 (6)	0.454 (3)
O3A	−0.0873 (3)	0.2900 (2)	0.40205 (15)	0.0233 (5)	0.546 (3)
C14	0.28177 (17)	0.49017 (15)	0.32527 (12)	0.0190 (2)
C11	0.42810 (16)	0.59660 (14)	0.25522 (11)	0.0150 (2)
C2	1.30647 (18)	0.76627 (15)	−0.19784 (11)	0.0184 (2)
H2	1.4071	0.7349	−0.2527	0.022*
C12	0.57032 (17)	0.61291 (14)	0.30963 (11)	0.0154 (2)
H12	0.5729	0.5581	0.3889	0.018*
C3	1.15984 (19)	0.66937 (15)	−0.14106 (11)	0.0182 (2)
H3	1.1633	0.5762	−0.1601	0.022*
C13	0.70819 (17)	0.71100 (14)	0.24559 (11)	0.0150 (2)
H13	0.8022	0.7211	0.2825	0.018*
C4	1.01368 (18)	0.71293 (14)	−0.05839 (11)	0.0162 (2)
H4	0.9193	0.6479	−0.0212	0.019*
C8	0.70666 (16)	0.79454 (13)	0.12608 (10)	0.0131 (2)
C5	1.00256 (16)	0.85677 (13)	−0.02763 (10)	0.0125 (2)
C9	0.56427 (17)	0.77658 (15)	0.07225 (11)	0.0169 (2)
H9	0.5617	0.8311	−0.0070	0.020*
C6	0.85491 (16)	0.90049 (13)	0.05981 (10)	0.0122 (2)
C10	0.42612 (17)	0.67810 (15)	0.13579 (11)	0.0177 (2)
H10	0.3330	0.6667	0.0988	0.021*
C7	0.85080 (16)	1.04271 (13)	0.08750 (10)	0.0121 (2)
C1	1.30091 (17)	0.90528 (14)	−0.17245 (11)	0.0156 (2)
H1	1.3976	0.9675	−0.2111	0.019*
C16	−0.1639 (2)	0.0255 (2)	0.70127 (14)	0.0414 (5)
H16A	−0.1440	−0.0882	0.7121	0.062*
H16B	−0.2785	0.0544	0.7531	0.062*
H16C	−0.0545	0.0525	0.7188	0.062*
C17	−0.3379 (2)	0.0787 (2)	0.53592 (14)	0.0345 (4)
H17A	−0.3238	0.1271	0.4521	0.052*
H17B	−0.4617	0.1220	0.5725	0.052*
H17C	−0.3286	−0.0357	0.5540	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0178 (5)	0.0232 (5)	0.0170 (5)	−0.0046 (4)	−0.0025 (4)	−0.0048 (4)
O2A	0.0313 (6)	0.0491 (7)	0.0211 (5)	−0.0239 (5)	−0.0063 (4)	0.0067 (5)
O1A	0.0249 (5)	0.0433 (6)	0.0266 (5)	−0.0223 (5)	−0.0065 (4)	0.0009 (5)
O1B	0.0249 (5)	0.0433 (6)	0.0266 (5)	−0.0223 (5)	−0.0065 (4)	0.0009 (5)
O2B	0.0313 (6)	0.0491 (7)	0.0211 (5)	−0.0239 (5)	−0.0063 (4)	0.0067 (5)
C15A	0.0178 (5)	0.0248 (6)	0.0223 (6)	−0.0060 (5)	−0.0015 (5)	−0.0088 (5)
C15B	0.0178 (5)	0.0248 (6)	0.0223 (6)	−0.0060 (5)	−0.0015 (5)	−0.0088 (5)
O3B	0.0284 (12)	0.0343 (13)	0.0215 (11)	−0.0195 (10)	−0.0028 (9)	−0.0007 (9)
O3A	0.0224 (9)	0.0300 (10)	0.0182 (9)	−0.0149 (7)	−0.0025 (6)	−0.0018 (7)
C14	0.0147 (5)	0.0178 (5)	0.0238 (6)	−0.0054 (4)	0.0006 (4)	−0.0059 (5)
C11	0.0125 (5)	0.0139 (5)	0.0179 (6)	−0.0045 (4)	−0.0006 (4)	−0.0034 (4)
C2	0.0206 (6)	0.0162 (5)	0.0166 (6)	−0.0029 (4)	0.0019 (4)	−0.0060 (4)
C12	0.0167 (5)	0.0156 (5)	0.0134 (5)	−0.0050 (4)	−0.0017 (4)	−0.0027 (4)
C3	0.0243 (6)	0.0136 (5)	0.0174 (6)	−0.0048 (4)	−0.0002 (5)	−0.0065 (4)
C13	0.0148 (5)	0.0168 (5)	0.0148 (5)	−0.0062 (4)	−0.0024 (4)	−0.0041 (4)
C4	0.0192 (5)	0.0137 (5)	0.0160 (5)	−0.0055 (4)	−0.0016 (4)	−0.0040 (4)
C8	0.0128 (5)	0.0126 (5)	0.0140 (5)	−0.0042 (4)	−0.0007 (4)	−0.0038 (4)
C5	0.0135 (5)	0.0124 (5)	0.0122 (5)	−0.0039 (4)	−0.0026 (4)	−0.0028 (4)
C9	0.0173 (5)	0.0176 (5)	0.0153 (5)	−0.0068 (4)	−0.0051 (4)	−0.0003 (4)
C6	0.0128 (5)	0.0119 (5)	0.0121 (5)	−0.0041 (4)	−0.0030 (4)	−0.0015 (4)
C10	0.0160 (5)	0.0185 (5)	0.0195 (6)	−0.0072 (4)	−0.0060 (4)	−0.0017 (4)
C7	0.0126 (5)	0.0122 (5)	0.0117 (5)	−0.0030 (4)	−0.0028 (4)	−0.0025 (4)
C1	0.0146 (5)	0.0158 (5)	0.0154 (5)	−0.0040 (4)	0.0000 (4)	−0.0040 (4)
C16	0.0237 (7)	0.0586 (11)	0.0228 (7)	−0.0014 (7)	−0.0047 (6)	0.0097 (7)
C17	0.0322 (8)	0.0537 (10)	0.0269 (8)	−0.0266 (7)	0.0019 (6)	−0.0157 (7)

Geometric parameters (Å, º)

N1—C15B	1.3249 (18)	C3—H3	0.9300
N1—C15A	1.3249 (18)	C13—C8	1.4016 (17)
N1—C17	1.4498 (18)	C13—H13	0.9300
N1—C16	1.4545 (19)	C4—C5	1.4357 (16)
O2A—C14	1.2613 (17)	C4—H4	0.9300
O1A—C14	1.2708 (16)	C8—C9	1.4011 (16)
O1A—H11A	0.8200	C8—C6	1.4955 (16)
O1B—C14	1.2708 (16)	C5—C6	1.4124 (16)
O2B—C14	1.2613 (17)	C5—C7^i	1.4453 (16)
O2B—H11B	0.8200	C9—C10	1.3960 (17)
C15A—O3A	1.306 (2)	C9—H9	0.9300
C15A—H15A	0.9300	C6—C7	1.4125 (16)
C15B—O3B	1.270 (3)	C10—H10	0.9300
C15B—H15B	0.9300	C7—C1^i	1.4353 (17)
C14—C11	1.4965 (18)	C7—C5^i	1.4454 (16)
C11—C10	1.3980 (18)	C1—C7^i	1.4353 (17)
C11—C12	1.3985 (17)	C1—H1	0.9300
C2—C1	1.3671 (17)	C16—H16A	0.9600
C2—C3	1.4208 (18)	C16—H16B	0.9600
C2—H2	0.9300	C16—H16C	0.9600
C12—C13	1.3936 (17)	C17—H17A	0.9600
C12—H12	0.9300	C17—H17B	0.9600
C3—C4	1.3675 (18)	C17—H17C	0.9600
C15B—N1—C17	121.69 (12)	C3—C4—H4	119.2
C15A—N1—C17	121.69 (12)	C5—C4—H4	119.2
C15B—N1—C16	121.36 (13)	C9—C8—C13	118.59 (11)
C15A—N1—C16	121.36 (13)	C9—C8—C6	121.85 (10)
C17—N1—C16	116.94 (13)	C13—C8—C6	119.56 (10)
C14—O1A—H11A	109.5	C6—C5—C4	121.86 (11)
C14—O2B—H11B	109.5	C6—C5—C7^i	119.75 (10)
O3A—C15A—N1	120.68 (13)	C4—C5—C7^i	118.38 (10)
O3A—C15A—H15A	119.7	C10—C9—C8	121.03 (11)
N1—C15A—H15A	119.7	C10—C9—H9	119.5
O3B—C15B—N1	116.33 (15)	C8—C9—H9	119.5
O3B—C15B—H15B	121.8	C5—C6—C7	119.77 (10)
N1—C15B—H15B	121.8	C5—C6—C8	120.48 (10)
O2A—C14—O1A	123.83 (12)	C7—C6—C8	119.72 (10)
O2B—C14—O1B	123.83 (12)	C9—C10—C11	119.83 (11)
O2B—C14—C11	118.10 (12)	C9—C10—H10	120.1
O2A—C14—C11	118.10 (12)	C11—C10—H10	120.1
O1A—C14—C11	118.06 (12)	C6—C7—C1^i	121.52 (10)
O1B—C14—C11	118.06 (12)	C6—C7—C5^i	120.48 (10)
C10—C11—C12	119.60 (11)	C1^i—C7—C5^i	117.98 (10)
C10—C11—C14	120.88 (11)	C2—C1—C7^i	121.48 (11)
C12—C11—C14	119.52 (11)	C2—C1—H1	119.3
C1—C2—C3	120.57 (11)	C7^i—C1—H1	119.3
C1—C2—H2	119.7	N1—C16—H16A	109.5
C3—C2—H2	119.7	N1—C16—H16B	109.5
C13—C12—C11	120.27 (11)	H16A—C16—H16B	109.5
C13—C12—H12	119.9	N1—C16—H16C	109.5
C11—C12—H12	119.9	H16A—C16—H16C	109.5
C4—C3—C2	120.07 (11)	H16B—C16—H16C	109.5
C4—C3—H3	120.0	N1—C17—H17A	109.5
C2—C3—H3	120.0	N1—C17—H17B	109.5
C12—C13—C8	120.68 (11)	H17A—C17—H17B	109.5
C12—C13—H13	119.7	N1—C17—H17C	109.5
C8—C13—H13	119.7	H17A—C17—H17C	109.5
C3—C4—C5	121.50 (11)	H17B—C17—H17C	109.5

Symmetry code: (i) −x+2, −y+2, −z.

catena-Poly[[bis(dimethylformamide-κO)zinc(II)]-µ-4,4'-(anthracene-9,10-diyl)dibenzoato-κ²O:O'] (ZnabdDMF2n)

Crystal data

[Zn(C28H16O4)(C3H7NO)2]	F(000) = 1304.0
Mr = 627.99	Dx = 1.403 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.991 (2) Å	Cell parameters from 5354 reflections
b = 6.8676 (10) Å	θ = 1.6–33.0°
c = 25.805 (4) Å	µ = 0.88 mm^−1
β = 99.036 (2)°	T = 130 K
V = 2973.7 (7) Å^3	Block-like crystals, yellow
Z = 4	0.15 × 0.12 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer	4414 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
ω and phi scans	θmax = 33.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −25→26
Tmin = 0.652, Tmax = 0.747	k = −10→10
25306 measured reflections	l = −38→38
5354 independent reflections

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) = 0.104	H-atom parameters constrained
S = 0.93	w = 1/[σ^2(Fo^2) + (0.0651P)^2 + 3.2151P] where P = (Fo^2 + 2Fc^2)/3
5354 reflections	(Δ/σ)max < 0.001
197 parameters	Δρmax = 0.89 e Å^−3
0 restraints	Δρmin = −0.85 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
Zn1	0.5000	0.48922 (3)	0.2500	0.01392 (7)
O1	0.44995 (6)	0.66790 (15)	0.29302 (4)	0.0193 (2)
O2	0.38484 (7)	0.41162 (16)	0.31891 (4)	0.0243 (2)
O3	0.43283 (8)	0.31228 (18)	0.20102 (4)	0.0281 (3)
N1	0.36825 (9)	0.0261 (2)	0.18372 (6)	0.0252 (3)
C11	0.36808 (8)	0.72185 (19)	0.35756 (5)	0.0138 (2)
C9	0.29858 (8)	0.7731 (2)	0.43170 (5)	0.0155 (2)
H9	0.2725	0.7220	0.4578	0.019*
C7	0.33301 (8)	1.22669 (19)	0.49978 (5)	0.0136 (2)
C5	0.19545 (8)	1.13462 (19)	0.46538 (5)	0.0138 (2)
C8	0.30820 (8)	0.97525 (19)	0.42812 (5)	0.0138 (2)
C12	0.37802 (8)	0.9229 (2)	0.35410 (5)	0.0161 (2)
H12	0.4050	0.9738	0.3285	0.019*
C13	0.34806 (9)	1.0477 (2)	0.38861 (6)	0.0169 (3)
H13	0.3546	1.1814	0.3854	0.020*
C10	0.32770 (8)	0.64794 (19)	0.39656 (5)	0.0154 (2)
H10	0.3202	0.5143	0.3991	0.019*
C6	0.27822 (8)	1.11323 (18)	0.46548 (5)	0.0131 (2)
C1	0.08222 (8)	1.2948 (2)	0.49770 (6)	0.0177 (3)
H1	0.0628	1.3859	0.5192	0.021*
C14	0.40237 (8)	0.5868 (2)	0.32086 (5)	0.0153 (2)
C2	0.02968 (9)	1.1847 (2)	0.46457 (6)	0.0207 (3)
H2	−0.0248	1.1997	0.4643	0.025*
C4	0.13769 (9)	1.0248 (2)	0.43047 (6)	0.0169 (2)
H4	0.1551	0.9367	0.4074	0.020*
C3	0.05762 (9)	1.0468 (2)	0.43044 (6)	0.0201 (3)
H3	0.0214	0.9717	0.4081	0.024*
C15	0.38915 (10)	0.1785 (2)	0.21361 (6)	0.0241 (3)
H15	0.3707	0.1875	0.2456	0.029*
C17	0.39833 (13)	−0.0016 (3)	0.13428 (9)	0.0374 (4)
H17A	0.3543	−0.0158	0.1063	0.056*
H17B	0.4308	−0.1166	0.1364	0.056*
H17C	0.4296	0.1093	0.1276	0.056*
C18	0.31756 (13)	−0.1269 (3)	0.19999 (9)	0.0415 (5)
H18A	0.3450	−0.2495	0.2011	0.062*
H18B	0.2690	−0.1346	0.1754	0.062*
H18C	0.3054	−0.0973	0.2342	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.02033 (11)	0.00950 (11)	0.01363 (11)	0.000	0.00797 (8)	0.000
O1	0.0257 (5)	0.0159 (5)	0.0196 (5)	0.0005 (4)	0.0135 (4)	−0.0006 (4)
O2	0.0364 (6)	0.0149 (5)	0.0258 (5)	−0.0037 (4)	0.0179 (5)	−0.0062 (4)
O3	0.0392 (7)	0.0253 (6)	0.0215 (5)	−0.0133 (5)	0.0103 (5)	−0.0063 (4)
N1	0.0266 (6)	0.0182 (6)	0.0282 (7)	−0.0023 (5)	−0.0039 (5)	−0.0022 (5)
C11	0.0173 (5)	0.0124 (5)	0.0130 (5)	0.0013 (4)	0.0061 (4)	−0.0008 (4)
C9	0.0207 (6)	0.0126 (5)	0.0153 (6)	0.0001 (5)	0.0092 (5)	−0.0003 (4)
C7	0.0159 (5)	0.0109 (5)	0.0147 (5)	0.0022 (4)	0.0049 (4)	0.0001 (4)
C5	0.0167 (5)	0.0114 (5)	0.0141 (5)	0.0019 (4)	0.0048 (4)	0.0005 (4)
C8	0.0168 (5)	0.0119 (5)	0.0136 (5)	0.0023 (4)	0.0052 (4)	−0.0001 (4)
C12	0.0217 (6)	0.0125 (6)	0.0158 (6)	0.0014 (5)	0.0085 (5)	0.0012 (5)
C13	0.0229 (6)	0.0109 (5)	0.0185 (6)	0.0020 (5)	0.0085 (5)	0.0007 (5)
C10	0.0205 (6)	0.0106 (5)	0.0170 (6)	0.0002 (5)	0.0083 (5)	−0.0004 (4)
C6	0.0172 (5)	0.0094 (5)	0.0137 (5)	0.0025 (4)	0.0053 (4)	−0.0001 (4)
C1	0.0168 (6)	0.0183 (6)	0.0190 (6)	0.0043 (5)	0.0060 (5)	−0.0010 (5)
C14	0.0189 (6)	0.0150 (6)	0.0129 (5)	0.0022 (5)	0.0055 (5)	−0.0012 (5)
C2	0.0151 (6)	0.0233 (7)	0.0241 (7)	0.0022 (5)	0.0043 (5)	−0.0004 (6)
C4	0.0201 (6)	0.0135 (6)	0.0173 (6)	0.0013 (5)	0.0031 (5)	−0.0017 (5)
C3	0.0193 (6)	0.0187 (6)	0.0213 (7)	−0.0006 (5)	0.0004 (5)	−0.0015 (5)
C15	0.0286 (7)	0.0229 (7)	0.0211 (7)	−0.0057 (6)	0.0041 (6)	−0.0023 (6)
C17	0.0397 (10)	0.0326 (10)	0.0392 (10)	0.0032 (8)	0.0037 (8)	−0.0197 (8)
C18	0.0407 (10)	0.0287 (9)	0.0479 (11)	−0.0168 (8)	−0.0151 (9)	0.0092 (8)

Geometric parameters (Å, º)

Zn1—O1^i	1.9385 (10)	C8—C13	1.4007 (18)
Zn1—O1	1.9385 (10)	C8—C6	1.4971 (17)
Zn1—O3	1.9808 (12)	C12—C13	1.3889 (19)
Zn1—O3^i	1.9808 (12)	C12—H12	0.9300
O1—C14	1.2892 (16)	C13—H13	0.9300
O2—C14	1.2388 (18)	C10—H10	0.9300
O3—C15	1.2557 (19)	C1—C2	1.364 (2)
N1—C15	1.315 (2)	C1—C7^ii	1.4391 (19)
N1—C17	1.460 (3)	C1—H1	0.9300
N1—C18	1.462 (2)	C2—C3	1.424 (2)
C11—C12	1.3958 (19)	C2—H2	0.9300
C11—C10	1.3991 (18)	C4—C3	1.369 (2)
C11—C14	1.5066 (18)	C4—H4	0.9300
C9—C10	1.3954 (18)	C3—H3	0.9300
C9—C8	1.4027 (18)	C15—H15	0.9300
C9—H9	0.9300	C17—H17A	0.9600
C7—C6	1.4136 (18)	C17—H17B	0.9600
C7—C1^ii	1.4390 (19)	C17—H17C	0.9600
C7—C5^ii	1.4443 (18)	C18—H18A	0.9600
C5—C6	1.4136 (18)	C18—H18B	0.9600
C5—C4	1.4373 (19)	C18—H18C	0.9600
C5—C7^ii	1.4442 (18)
O1^i—Zn1—O1	101.45 (6)	C11—C10—H10	119.7
O1^i—Zn1—O3	106.47 (5)	C5—C6—C7	120.07 (11)
O1—Zn1—O3	119.55 (5)	C5—C6—C8	120.24 (12)
O1^i—Zn1—O3^i	119.55 (5)	C7—C6—C8	119.66 (11)
O1—Zn1—O3^i	106.47 (5)	C2—C1—C7^ii	121.56 (12)
O3—Zn1—O3^i	104.32 (8)	C2—C1—H1	119.2
C14—O1—Zn1	114.56 (9)	C7^ii—C1—H1	119.2
C15—O3—Zn1	126.06 (11)	O2—C14—O1	124.38 (12)
C15—N1—C17	121.13 (15)	O2—C14—C11	120.60 (12)
C15—N1—C18	121.38 (17)	O1—C14—C11	115.02 (12)
C17—N1—C18	117.41 (16)	C1—C2—C3	120.48 (13)
C12—C11—C10	118.87 (12)	C1—C2—H2	119.8
C12—C11—C14	120.40 (11)	C3—C2—H2	119.8
C10—C11—C14	120.70 (12)	C3—C4—C5	121.55 (13)
C10—C9—C8	120.65 (12)	C3—C4—H4	119.2
C10—C9—H9	119.7	C5—C4—H4	119.2
C8—C9—H9	119.7	C4—C3—C2	120.05 (13)
C6—C7—C1^ii	121.85 (12)	C4—C3—H3	120.0
C6—C7—C5^ii	120.08 (11)	C2—C3—H3	120.0
C1^ii—C7—C5^ii	118.04 (12)	O3—C15—N1	123.14 (15)
C6—C5—C4	121.86 (12)	O3—C15—H15	118.4
C6—C5—C7^ii	119.85 (12)	N1—C15—H15	118.4
C4—C5—C7^ii	118.28 (12)	N1—C17—H17A	109.5
C13—C8—C9	118.31 (12)	N1—C17—H17B	109.5
C13—C8—C6	119.75 (12)	H17A—C17—H17B	109.5
C9—C8—C6	121.94 (11)	N1—C17—H17C	109.5
C13—C12—C11	120.60 (12)	H17A—C17—H17C	109.5
C13—C12—H12	119.7	H17B—C17—H17C	109.5
C11—C12—H12	119.7	N1—C18—H18A	109.5
C12—C13—C8	121.02 (13)	N1—C18—H18B	109.5
C12—C13—H13	119.5	H18A—C18—H18B	109.5
C8—C13—H13	119.5	N1—C18—H18C	109.5
C9—C10—C11	120.53 (12)	H18A—C18—H18C	109.5
C9—C10—H10	119.7	H18B—C18—H18C	109.5

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

catena-Poly[[[bis(N,N-dimethylacetamide-κO)zinc(II)]-µ-4,4'-(anthracene-9,10-diyl)dibenzoato-κ²O:O'] N,N-dimethylacetamide monosolvate] (ZnabdDMA2_DMAn)

Crystal data

[Zn(C28H16O4)(C4H9NO)2]·C4H9NO	F(000) = 1368.0
Mr = 656.04	Dx = 1.261 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.292 (4) Å	Cell parameters from 5043 reflections
b = 9.284 (3) Å	θ = 1.5–30.0°
c = 28.005 (8) Å	µ = 0.76 mm^−1
β = 90.333 (4)°	T = 106 K
V = 3455.7 (16) Å^3	Plate-like, colorless
Z = 4	0.10 × 0.06 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer	4328 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.051
ω and phi scans	θmax = 30.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2017)	h = −18→18
Tmin = 0.657, Tmax = 0.746	k = −13→13
26640 measured reflections	l = −39→39
5042 independent reflections

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.149	H-atom parameters constrained
S = 1.27	w = 1/[σ^2(Fo^2) + (0.0126P)^2 + 26.2068P] where P = (Fo^2 + 2Fc^2)/3
5042 reflections	(Δ/σ)max < 0.001
207 parameters	Δρmax = 0.55 e Å^−3
0 restraints	Δρmin = −0.85 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
Zn1	0.5000	0.89381 (6)	0.7500	0.01388 (13)
N1	0.6493 (2)	1.2753 (3)	0.73256 (11)	0.0212 (6)
O1	0.5746 (2)	0.7399 (3)	0.67476 (12)	0.0393 (8)
C1	0.4826 (3)	0.7222 (3)	0.67421 (11)	0.0172 (6)
O2	0.42280 (19)	0.7891 (3)	0.70212 (9)	0.0246 (5)
C2	0.4349 (2)	0.6186 (3)	0.63945 (11)	0.0145 (6)
O3	0.60681 (19)	1.0426 (3)	0.73747 (9)	0.0237 (5)
C3	0.3330 (3)	0.5886 (4)	0.64116 (14)	0.0287 (9)
H3	0.2936	0.6309	0.6646	0.034*
C4	0.2890 (3)	0.4958 (5)	0.60808 (16)	0.0349 (11)
H4	0.2206	0.4760	0.6100	0.042*
C6	0.4491 (2)	0.4596 (3)	0.57131 (12)	0.0174 (6)
H6	0.4888	0.4161	0.5482	0.021*
C5	0.3458 (2)	0.4321 (3)	0.57223 (11)	0.0149 (6)
C7	0.4932 (2)	0.5517 (4)	0.60474 (12)	0.0189 (6)
H7	0.5621	0.5686	0.6039	0.023*
C8	0.2689 (2)	0.3984 (4)	0.49082 (11)	0.0154 (6)
C9	0.2972 (2)	0.3382 (4)	0.53505 (11)	0.0146 (6)
C10	0.2787 (2)	0.1918 (4)	0.54483 (11)	0.0150 (6)
C11	0.3075 (2)	0.1276 (4)	0.58946 (12)	0.0189 (7)
H11	0.3378	0.1843	0.6128	0.023*
C12	0.2911 (2)	−0.0153 (4)	0.59826 (12)	0.0188 (6)
H12	0.3114	−0.0551	0.6272	0.023*
C13	0.2431 (2)	−0.1032 (4)	0.56338 (12)	0.0203 (6)
H13	0.2312	−0.1999	0.5699	0.024*
C14	0.2144 (2)	−0.0469 (4)	0.52027 (12)	0.0175 (6)
H14	0.1835	−0.1062	0.4978	0.021*
C15	0.5370 (3)	1.1756 (5)	0.67127 (13)	0.0311 (9)
H15A	0.4993	1.0886	0.6664	0.047*
H15B	0.5801	1.1916	0.6444	0.047*
H15C	0.4915	1.2553	0.6745	0.047*
C16	0.5998 (2)	1.1620 (4)	0.71583 (12)	0.0180 (6)
C17	0.7131 (3)	1.2638 (4)	0.77511 (14)	0.0289 (8)
H17A	0.7041	1.3476	0.7947	0.043*
H17B	0.7823	1.2570	0.7657	0.043*
H17C	0.6948	1.1793	0.7928	0.043*
C18	0.6493 (4)	1.4179 (5)	0.70999 (18)	0.0435 (12)
H18A	0.7167	1.4550	0.7094	0.065*
H18B	0.6072	1.4820	0.7279	0.065*
H18C	0.6239	1.4100	0.6779	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0170 (2)	0.0093 (2)	0.0153 (2)	0.000	−0.00776 (18)	0.000
N1	0.0226 (14)	0.0167 (14)	0.0244 (15)	−0.0034 (11)	−0.0048 (11)	0.0051 (11)
O1	0.0244 (14)	0.0384 (17)	0.055 (2)	−0.0053 (12)	−0.0095 (13)	−0.0261 (15)
C1	0.0268 (16)	0.0100 (13)	0.0147 (14)	−0.0015 (12)	−0.0077 (12)	−0.0006 (11)
O2	0.0264 (13)	0.0259 (13)	0.0213 (12)	−0.0045 (10)	−0.0042 (10)	−0.0097 (10)
C2	0.0190 (14)	0.0102 (13)	0.0141 (13)	−0.0010 (11)	−0.0051 (11)	0.0012 (11)
O3	0.0251 (13)	0.0148 (12)	0.0312 (14)	−0.0012 (10)	−0.0090 (11)	0.0000 (10)
C3	0.0208 (16)	0.038 (2)	0.0276 (18)	−0.0045 (16)	0.0032 (14)	−0.0223 (17)
C4	0.0112 (15)	0.051 (3)	0.043 (2)	−0.0061 (16)	−0.0002 (15)	−0.035 (2)
C6	0.0144 (14)	0.0157 (15)	0.0219 (16)	−0.0014 (12)	0.0001 (12)	−0.0066 (12)
C5	0.0146 (14)	0.0150 (14)	0.0152 (14)	0.0009 (11)	−0.0052 (11)	−0.0054 (11)
C7	0.0142 (14)	0.0164 (15)	0.0259 (17)	−0.0034 (12)	−0.0035 (12)	−0.0048 (13)
C8	0.0097 (12)	0.0184 (15)	0.0181 (14)	−0.0001 (12)	−0.0015 (10)	−0.0050 (13)
C9	0.0088 (12)	0.0187 (15)	0.0161 (14)	0.0020 (11)	−0.0027 (11)	−0.0082 (12)
C10	0.0110 (13)	0.0185 (15)	0.0155 (15)	0.0046 (11)	−0.0032 (11)	−0.0075 (12)
C11	0.0154 (14)	0.0211 (17)	0.0202 (15)	0.0028 (12)	−0.0059 (12)	−0.0069 (13)
C12	0.0161 (15)	0.0237 (17)	0.0168 (15)	0.0012 (12)	−0.0033 (12)	−0.0033 (13)
C13	0.0188 (15)	0.0201 (15)	0.0220 (16)	−0.0035 (13)	0.0001 (12)	−0.0019 (14)
C14	0.0139 (14)	0.0212 (16)	0.0176 (15)	−0.0031 (12)	−0.0002 (11)	−0.0055 (12)
C15	0.034 (2)	0.040 (2)	0.0191 (17)	−0.0133 (18)	−0.0094 (15)	0.0072 (16)
C16	0.0152 (14)	0.0214 (16)	0.0173 (15)	−0.0009 (12)	0.0020 (11)	−0.0008 (12)
C17	0.0284 (19)	0.0252 (19)	0.033 (2)	−0.0088 (15)	−0.0138 (16)	0.0034 (16)
C18	0.051 (3)	0.025 (2)	0.055 (3)	−0.0121 (19)	−0.017 (2)	0.019 (2)

Geometric parameters (Å, º)

Zn1—O2^i	1.944 (2)	C8—C14^ii	1.431 (5)
Zn1—O2	1.944 (2)	C8—C10^ii	1.446 (4)
Zn1—O3	2.013 (3)	C9—C10	1.409 (5)
Zn1—O3^i	2.013 (3)	C10—C11	1.435 (5)
N1—C16	1.325 (4)	C10—C8^ii	1.446 (4)
N1—C17	1.462 (4)	C11—C12	1.367 (5)
N1—C18	1.467 (5)	C11—H11	0.9300
O1—C1	1.234 (4)	C12—C13	1.421 (5)
C1—O2	1.279 (4)	C12—H12	0.9300
C1—C2	1.506 (4)	C13—C14	1.368 (5)
C2—C3	1.383 (5)	C13—H13	0.9300
C2—C7	1.393 (5)	C14—C8^ii	1.431 (5)
O3—C16	1.266 (4)	C14—H14	0.9300
C3—C4	1.392 (5)	C15—C16	1.503 (5)
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.391 (5)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
C6—C7	1.394 (4)	C17—H17A	0.9600
C6—C5	1.398 (4)	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
C5—C9	1.501 (4)	C18—H18A	0.9600
C7—H7	0.9300	C18—H18B	0.9600
C8—C9	1.408 (4)	C18—H18C	0.9600
O2^i—Zn1—O2	120.01 (17)	C10—C9—C5	120.0 (3)
O2^i—Zn1—O3	95.36 (11)	C9—C10—C11	121.6 (3)
O2—Zn1—O3	126.35 (11)	C9—C10—C8^ii	120.0 (3)
O2^i—Zn1—O3^i	126.35 (11)	C11—C10—C8^ii	118.3 (3)
O2—Zn1—O3^i	95.35 (11)	C12—C11—C10	121.2 (3)
O3—Zn1—O3^i	93.34 (15)	C12—C11—H11	119.4
C16—N1—C17	121.0 (3)	C10—C11—H11	119.4
C16—N1—C18	124.4 (3)	C11—C12—C13	120.3 (3)
C17—N1—C18	114.5 (3)	C11—C12—H12	119.8
O1—C1—O2	123.1 (3)	C13—C12—H12	119.8
O1—C1—C2	120.5 (3)	C14—C13—C12	120.6 (3)
O2—C1—C2	116.4 (3)	C14—C13—H13	119.7
C1—O2—Zn1	109.7 (2)	C12—C13—H13	119.7
C3—C2—C7	118.9 (3)	C13—C14—C8^ii	121.1 (3)
C3—C2—C1	121.0 (3)	C13—C14—H14	119.4
C7—C2—C1	120.1 (3)	C8^ii—C14—H14	119.4
C16—O3—Zn1	129.4 (2)	C16—C15—H15A	109.5
C2—C3—C4	120.6 (3)	C16—C15—H15B	109.5
C2—C3—H3	119.7	H15A—C15—H15B	109.5
C4—C3—H3	119.7	C16—C15—H15C	109.5
C5—C4—C3	121.1 (3)	H15A—C15—H15C	109.5
C5—C4—H4	119.5	H15B—C15—H15C	109.5
C3—C4—H4	119.5	O3—C16—N1	119.4 (3)
C7—C6—C5	120.6 (3)	O3—C16—C15	120.7 (3)
C7—C6—H6	119.7	N1—C16—C15	119.9 (3)
C5—C6—H6	119.7	N1—C17—H17A	109.5
C4—C5—C6	118.2 (3)	N1—C17—H17B	109.5
C4—C5—C9	121.0 (3)	H17A—C17—H17B	109.5
C6—C5—C9	120.8 (3)	N1—C17—H17C	109.5
C2—C7—C6	120.6 (3)	H17A—C17—H17C	109.5
C2—C7—H7	119.7	H17B—C17—H17C	109.5
C6—C7—H7	119.7	N1—C18—H18A	109.5
C9—C8—C14^ii	122.2 (3)	N1—C18—H18B	109.5
C9—C8—C10^ii	119.4 (3)	H18A—C18—H18B	109.5
C14^ii—C8—C10^ii	118.4 (3)	N1—C18—H18C	109.5
C8—C9—C10	120.5 (3)	H18A—C18—H18C	109.5
C8—C9—C5	119.4 (3)	H18B—C18—H18C	109.5

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