Three coordination polymers built by quaternary-ammonium-modified isophthalic acid

Wang, L.-F.; Liu, X.-G.; Meng, M.-M.; Xu, Y.-K.; Zhu, R.; Zhang, R.; Lu, Z.-Z.; Huang, W.

doi:10.1107/S2053229621003296

Three coordination polymers built by quaternary-ammonium-modified isophthalic acid

L.-F. Wang, X.-G. Liu, M.-M. Meng, Y.-K. Xu, R. Zhu, R. Zhang, Z.-Z. Lu and W. Huang

Three coordination polymers based on quaternary-ammonium-modified isophthalic acid, namely, catena-poly[[[aqua-μ₂-bromido-di-μ₃-hydroxido-methanoldinitratotetracopper(II)]-bis{μ₄-5-[2-(tripropylazaniumyl)ethoxy]benzene-1,3-dicarboxylato}] nitrate], {[Cu₄Br(C₁₉H₂₈NO₅)₂(NO₃)₂(OH)₂(CH₄O)(H₂O)]NO₃}_n, 1, poly[μ₃-bromido-μ₂-bromido-bromido-μ₃-hydroxido-{μ₄-5-[2-(tripropylazaniumyl)ethoxy]benzene-1,3-dicarboxylato}tricopper(II)], [Cu₃Br₃(C₁₉H₂₈NO₅)(OH)]_n, 2, and poly[bromido{μ₃-5-[2-(tripropylazaniumyl)ethoxy]benzene-1,3-dicarboxylato}zinc(II)], [ZnBr(C₁₉H₂₈NO₅)]_n, 3, were obtained by solvothermal reactions. Coordination polymer (CP) 1 contains tetranuclear Cu₄ units, in which the four Cu atoms are linked by two μ₃-OH⁻ groups into a Cu₄(OH)₂ cluster, which are in turn linked by 5-[2-(tripropylazaniumyl)ethoxy]benzene-1,3-dicarboxylate (cpa⁻) ligands into a chain structure. CP 2 also contains a tetranuclear Cu₄(OH)₂ cluster and these are linked with CuBr₃ units into chains. The chains are then connected by cpa⁻ ligands into a two-dimensional layered structure. CP 3 contains a two-dimensional layer structure built by binuclear Zn₂ units and cpa⁻ ligands. The Br⁻ counter-anions of the quaternary ammonium groups all take part in the construction of the polymeric networks.

Keywords: metal-organic framework; MOF; crystal structure; quaternary ammonium; zinc; copper; isophthalate; coordination polymer.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229621003296/ov3146sup1.cif Contains datablocks 1, 2, 3, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229621003296/ov31461sup2.hkl Contains datablock 1
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229621003296/ov31462sup3.hkl Contains datablock 2
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229621003296/ov31463sup4.hkl Contains datablock 3

CCDC references: 2026903; 2026902; 2026901

Computing details top

For all structures, data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXS2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b). Molecular graphics: SHELXTL (Bruker, 2015) for (1), (2); OLEX2 (Dolomanov et al., 2009) for (3). Software used to prepare material for publication: SHELXTL (Bruker, 2015) for (1), (2); OLEX2 (Dolomanov et al., 2009) for (3).

catena-Poly[[[aqua-µ₂-bromido-di-µ₃-hydroxido-methanoldinitratotetracopper(II)]-bis{µ₄-5-[2-(tripropylazaniumyl)ethoxy]benzene-1,3-dicarboxylato}] nitrate] (1) top

Crystal data top

[Cu₄Br(C₁₉H₂₈NO₅)₂(NO₃)₂(OH)₂(CH₄O)(H₂O)]NO₃	Z = 2
M_r = 1305.02	F(000) = 1336
Triclinic, P1	D_x = 1.645 Mg m⁻³
a = 9.4872 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7297 (14) Å	Cell parameters from 3991 reflections
c = 25.920 (2) Å	θ = 2.3–27.5°
α = 89.116 (3)°	µ = 2.43 mm⁻¹
β = 87.262 (3)°	T = 296 K
γ = 89.258 (2)°	Block, blue
V = 2635.0 (6) Å³	0.28 × 0.24 × 0.22 mm

Data collection top

Bruker D8 diffractometer	7239 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.093
ω rotation scans	θ_max = 26.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2015)	h = −8→11
T_min = 0.55, T_max = 0.62	k = −13→13
22593 measured reflections	l = −31→31
10238 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0372P)² + 1.0708P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
10238 reflections	Δρ_max = 1.36 e Å⁻³
649 parameters	Δρ_min = −0.69 e Å⁻³
0 restraints

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.76224 (4)	−0.08840 (4)	0.17146 (2)	0.04306 (12)
C1	1.0389 (4)	0.2412 (3)	0.30155 (14)	0.0296 (8)
C2	0.9736 (4)	0.3549 (3)	0.29548 (13)	0.0310 (8)
H2	0.883928	0.360292	0.282512	0.037*
C3	1.0436 (4)	0.4624 (3)	0.30907 (14)	0.0324 (9)
C4	1.1770 (3)	0.4564 (3)	0.33007 (13)	0.0281 (8)
H4	1.221738	0.528291	0.339862	0.034*
C5	1.2410 (4)	0.3391 (3)	0.33589 (14)	0.0318 (8)
C6	1.1737 (4)	0.2319 (3)	0.32084 (14)	0.0315 (8)
H6	1.218310	0.154517	0.323610	0.038*
C7	0.9680 (4)	0.1232 (3)	0.28755 (15)	0.0338 (9)
C8	0.9745 (4)	0.5884 (3)	0.30102 (14)	0.0304 (8)
C9	0.4145 (4)	0.4745 (3)	0.21475 (13)	0.0288 (8)
C10	0.4777 (4)	0.3605 (3)	0.22694 (13)	0.0303 (8)
H10	0.564922	0.357858	0.241893	0.036*
C11	0.4090 (4)	0.2510 (3)	0.21648 (13)	0.0283 (8)
C12	0.2745 (4)	0.2543 (3)	0.19764 (13)	0.0313 (8)
H12	0.228113	0.180345	0.191826	0.038*
C13	0.2100 (4)	0.3667 (3)	0.18759 (14)	0.0306 (8)
C14	0.2801 (4)	0.4787 (3)	0.19522 (13)	0.0312 (8)
H14	0.237538	0.554760	0.187346	0.037*
C15	0.4873 (4)	0.5943 (3)	0.22367 (14)	0.0316 (8)
C16	0.4759 (4)	0.1280 (3)	0.22804 (14)	0.0304 (8)
C17	1.4658 (4)	0.4210 (3)	0.36160 (14)	0.0311 (8)
H17A	1.440233	0.465906	0.392922	0.037*
H17B	1.461458	0.478460	0.332447	0.037*
C18	1.6124 (4)	0.3661 (3)	0.36437 (14)	0.0320 (8)
H18A	1.679391	0.428815	0.352237	0.038*
H18B	1.621114	0.297059	0.340662	0.038*
C19	1.6852 (4)	0.4301 (3)	0.45089 (14)	0.0349 (9)
H19A	1.604704	0.486691	0.450569	0.042*
H19B	1.692205	0.399473	0.486091	0.042*
C20	1.8155 (4)	0.5039 (3)	0.43682 (15)	0.0378 (9)
H20A	1.805350	0.544982	0.403598	0.045*
H20B	1.896648	0.448001	0.433894	0.045*
C21	1.8397 (4)	0.6017 (3)	0.47795 (15)	0.0439 (10)
H21A	1.750851	0.638279	0.489228	0.066*
H21B	1.900393	0.665492	0.463483	0.066*
H21C	1.883055	0.562634	0.506855	0.066*
C22	1.7814 (4)	0.2375 (3)	0.40822 (14)	0.0334 (9)
H22A	1.852699	0.285002	0.388709	0.040*
H22B	1.755362	0.168928	0.386823	0.040*
C23	1.8469 (4)	0.1840 (4)	0.45547 (15)	0.0387 (9)
H23A	1.780496	0.128325	0.473311	0.046*
H23B	1.866283	0.251045	0.478689	0.046*
C24	1.9839 (4)	0.1125 (4)	0.44217 (16)	0.0507 (12)
H24A	2.022223	0.079893	0.473303	0.076*
H24B	1.964905	0.044971	0.419732	0.076*
H24C	2.050652	0.167632	0.425108	0.076*
C25	1.5378 (4)	0.2471 (3)	0.44526 (14)	0.0329 (9)
H25A	1.452578	0.298029	0.445739	0.039*
H25B	1.563139	0.234783	0.480817	0.039*
C26	1.5033 (4)	0.1193 (3)	0.42338 (14)	0.0339 (9)
H26A	1.489548	0.127153	0.386623	0.041*
H26B	1.581095	0.061412	0.428356	0.041*
C27	1.3702 (4)	0.0706 (3)	0.45100 (14)	0.0384 (9)
H27A	1.391898	0.040179	0.484775	0.058*
H27B	1.333209	0.003975	0.431578	0.058*
H27C	1.301361	0.136670	0.454124	0.058*
C28	−0.0036 (4)	0.4772 (3)	0.16589 (14)	0.0317 (8)
H28A	0.037263	0.530198	0.138605	0.038*
H28B	−0.002138	0.521481	0.198208	0.038*
C29	−0.1512 (4)	0.4459 (3)	0.15460 (14)	0.0322 (9)
H29A	−0.211791	0.513456	0.167181	0.039*
H29B	−0.176761	0.372111	0.174821	0.039*
C30	−0.0945 (4)	0.3191 (3)	0.07699 (14)	0.0339 (9)
H30A	0.003201	0.342128	0.080100	0.041*
H30B	−0.110664	0.313875	0.040421	0.041*
C31	−0.1145 (4)	0.1904 (3)	0.10100 (14)	0.0376 (9)
H31A	−0.209394	0.161804	0.095920	0.045*
H31B	−0.101071	0.193012	0.137830	0.045*
C32	−0.0061 (4)	0.1012 (3)	0.07508 (16)	0.0467 (11)
H32A	−0.045933	0.064302	0.045671	0.070*
H32B	0.018786	0.036856	0.099265	0.070*
H32C	0.076844	0.146624	0.064087	0.070*
C33	−0.3395 (4)	0.3883 (4)	0.10006 (14)	0.0346 (9)
H33A	−0.394222	0.457751	0.114276	0.041*
H33B	−0.353412	0.317913	0.123601	0.041*
C34	−0.3987 (4)	0.3553 (4)	0.04888 (14)	0.0380 (9)
H34A	−0.339510	0.291577	0.032469	0.046*
H34B	−0.397276	0.428421	0.026371	0.046*
C35	−0.5502 (4)	0.3079 (4)	0.05573 (16)	0.0437 (10)
H35A	−0.567555	0.279215	0.090692	0.066*
H35B	−0.562728	0.240451	0.032561	0.066*
H35C	−0.615094	0.374389	0.048243	0.066*
C36	−0.1556 (4)	0.5353 (3)	0.06466 (14)	0.0340 (9)
H36A	−0.174318	0.513804	0.029435	0.041*
H36B	−0.055796	0.552988	0.065556	0.041*
C37	−0.2384 (4)	0.6543 (3)	0.07813 (14)	0.0385 (9)
H37A	−0.337760	0.642063	0.072852	0.046*
H37B	−0.228331	0.673187	0.114238	0.046*
C38	−0.1848 (4)	0.7631 (3)	0.04456 (15)	0.0395 (9)
H38A	−0.090688	0.744753	0.031288	0.059*
H38B	−0.184248	0.837088	0.064881	0.059*
H38C	−0.245528	0.775908	0.016334	0.059*
C39	0.3886 (5)	0.9576 (4)	0.09553 (18)	0.0636 (14)
H39A	0.396861	1.038965	0.109853	0.095*
H39B	0.302283	0.953287	0.077779	0.095*
H39C	0.467126	0.941955	0.071680	0.095*
Cu1	1.03219 (5)	−0.14911 (4)	0.28867 (2)	0.03475 (12)
Cu2	0.71281 (5)	−0.00817 (4)	0.26893 (2)	0.03171 (12)
Cu3	0.48167 (5)	0.86298 (4)	0.20312 (2)	0.03553 (13)
Cu4	0.71186 (4)	0.71910 (4)	0.27648 (2)	0.03062 (12)
N1	1.6544 (3)	0.3197 (2)	0.41718 (11)	0.0278 (7)
N2	−0.1862 (3)	0.4223 (3)	0.09894 (11)	0.0321 (7)
N4	0.6185 (3)	0.7521 (3)	0.39588 (11)	0.0280 (7)
N5	0.2433 (3)	0.6385 (3)	0.07522 (10)	0.0270 (7)
O1	1.0475 (3)	0.0323 (2)	0.27743 (9)	0.0363 (6)
O2	0.8376 (2)	0.1253 (2)	0.28549 (10)	0.0337 (6)
O3	0.8548 (2)	0.5892 (2)	0.28186 (9)	0.0326 (6)
O4	1.0415 (2)	0.6799 (2)	0.31504 (10)	0.0357 (6)
O5	1.3712 (2)	0.3192 (2)	0.35568 (9)	0.0341 (6)
O6	0.4377 (3)	0.6897 (2)	0.20265 (10)	0.0370 (6)
O7	0.5985 (2)	0.5878 (2)	0.24809 (9)	0.0335 (6)
O8	0.5810 (2)	0.1280 (2)	0.25593 (9)	0.0320 (6)
O9	0.4235 (3)	0.0357 (2)	0.20695 (9)	0.0349 (6)
O10	0.0762 (2)	0.3625 (2)	0.16934 (9)	0.0319 (6)
O11	0.8280 (2)	−0.1429 (2)	0.30013 (10)	0.0330 (6)
H11A	0.812070	−0.138763	0.332611	0.040*
O12	0.5723 (2)	0.8571 (2)	0.26852 (9)	0.0309 (6)
H12B	0.513065	0.861025	0.294108	0.037*
O13	1.1700 (3)	−0.1094 (2)	0.36736 (10)	0.0409 (6)
N3	1.2706 (3)	−0.1263 (3)	0.33455 (12)	0.033
O14	1.3923 (3)	−0.1094 (2)	0.34930 (10)	0.0415 (7)
O15	1.2455 (3)	−0.1497 (2)	0.28878 (10)	0.0393 (6)
O16	0.7031 (3)	0.8405 (2)	0.39406 (10)	0.0385 (6)
O17	0.5397 (3)	0.7322 (3)	0.43481 (10)	0.0469 (7)
O18	0.6199 (3)	0.6777 (2)	0.35879 (10)	0.0378 (6)
O19	0.3877 (3)	0.8613 (2)	0.13820 (10)	0.0508 (8)
H19	0.339145	0.796928	0.133238	0.061*
O20	0.3739 (3)	0.6552 (2)	0.07651 (11)	0.0481 (7)
O21	0.1616 (3)	0.7140 (2)	0.09470 (11)	0.0475 (7)
O22	0.2098 (3)	0.5351 (3)	0.05766 (10)	0.0471 (7)
O1W	1.0560 (3)	−0.2075 (2)	0.20653 (10)	0.0438 (7)
H1Y	1.053435	−0.143314	0.186938	0.053*
H1X	0.988905	−0.255594	0.199968	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0449 (2)	0.0439 (2)	0.0398 (2)	−0.00974 (19)	0.00901 (19)	−0.01107 (18)
C1	0.0255 (19)	0.030 (2)	0.033 (2)	−0.0082 (16)	0.0051 (16)	−0.0087 (16)
C2	0.032 (2)	0.0258 (19)	0.036 (2)	−0.0022 (16)	−0.0117 (17)	−0.0073 (16)
C3	0.034 (2)	0.029 (2)	0.036 (2)	0.0037 (16)	−0.0100 (18)	−0.0099 (16)
C4	0.0215 (18)	0.0266 (19)	0.036 (2)	−0.0053 (15)	0.0024 (16)	−0.0073 (15)
C5	0.031 (2)	0.029 (2)	0.036 (2)	−0.0080 (16)	−0.0114 (17)	0.0094 (16)
C6	0.032 (2)	0.0265 (19)	0.036 (2)	0.0037 (16)	−0.0101 (17)	−0.0069 (16)
C7	0.035 (2)	0.0241 (19)	0.043 (2)	0.0001 (17)	−0.0118 (19)	0.0032 (16)
C8	0.0263 (19)	0.028 (2)	0.037 (2)	0.0034 (16)	0.0024 (17)	−0.0105 (16)
C9	0.031 (2)	0.0260 (19)	0.031 (2)	0.0039 (15)	−0.0097 (17)	−0.0088 (15)
C10	0.0303 (19)	0.028 (2)	0.033 (2)	0.0050 (15)	−0.0101 (17)	−0.0096 (16)
C11	0.0240 (18)	0.0251 (19)	0.035 (2)	0.0050 (15)	0.0041 (16)	−0.0065 (15)
C12	0.035 (2)	0.0262 (19)	0.033 (2)	−0.0065 (16)	−0.0099 (17)	0.0052 (16)
C13	0.031 (2)	0.0273 (19)	0.035 (2)	0.0038 (16)	−0.0095 (17)	−0.0097 (16)
C14	0.033 (2)	0.0270 (19)	0.035 (2)	−0.0008 (16)	−0.0092 (17)	−0.0075 (16)
C15	0.036 (2)	0.026 (2)	0.034 (2)	−0.0055 (16)	−0.0074 (18)	−0.0065 (16)
C16	0.0230 (18)	0.0261 (19)	0.042 (2)	−0.0002 (15)	0.0003 (17)	−0.0051 (17)
C17	0.0298 (19)	0.0271 (19)	0.037 (2)	−0.0053 (16)	−0.0079 (17)	0.0032 (16)
C18	0.033 (2)	0.029 (2)	0.034 (2)	0.0006 (16)	−0.0095 (17)	0.0027 (16)
C19	0.035 (2)	0.034 (2)	0.037 (2)	−0.0069 (17)	−0.0127 (18)	−0.0075 (17)
C20	0.034 (2)	0.038 (2)	0.042 (2)	−0.0055 (17)	−0.0090 (19)	−0.0080 (18)
C21	0.049 (2)	0.036 (2)	0.048 (3)	−0.0156 (19)	−0.017 (2)	−0.0059 (18)
C22	0.029 (2)	0.037 (2)	0.033 (2)	0.0102 (17)	0.0041 (17)	0.0081 (16)
C23	0.031 (2)	0.041 (2)	0.044 (2)	0.0080 (18)	−0.0064 (19)	0.0072 (18)
C24	0.038 (2)	0.064 (3)	0.048 (3)	0.021 (2)	0.011 (2)	0.022 (2)
C25	0.0282 (19)	0.039 (2)	0.032 (2)	−0.0071 (16)	−0.0077 (17)	−0.0068 (17)
C26	0.036 (2)	0.031 (2)	0.034 (2)	−0.0040 (17)	0.0039 (18)	0.0067 (16)
C27	0.042 (2)	0.038 (2)	0.034 (2)	−0.0104 (18)	0.0087 (19)	0.0081 (17)
C28	0.0279 (19)	0.032 (2)	0.036 (2)	0.0054 (16)	−0.0095 (17)	−0.0089 (16)
C29	0.031 (2)	0.034 (2)	0.032 (2)	0.0036 (16)	−0.0088 (17)	−0.0071 (16)
C30	0.037 (2)	0.033 (2)	0.032 (2)	−0.0079 (17)	−0.0077 (18)	−0.0069 (16)
C31	0.042 (2)	0.034 (2)	0.036 (2)	−0.0062 (18)	0.0081 (19)	−0.0069 (17)
C32	0.048 (3)	0.036 (2)	0.055 (3)	−0.005 (2)	0.019 (2)	0.0057 (19)
C33	0.031 (2)	0.042 (2)	0.031 (2)	−0.0093 (17)	−0.0113 (17)	0.0048 (17)
C34	0.035 (2)	0.043 (2)	0.037 (2)	−0.0107 (18)	−0.0132 (19)	0.0065 (18)
C35	0.042 (2)	0.044 (2)	0.047 (3)	−0.0141 (19)	−0.014 (2)	−0.0101 (19)
C36	0.0274 (19)	0.038 (2)	0.037 (2)	0.0031 (16)	−0.0091 (17)	0.0020 (17)
C37	0.041 (2)	0.039 (2)	0.035 (2)	0.0033 (18)	0.0064 (19)	0.0055 (17)
C38	0.036 (2)	0.040 (2)	0.042 (2)	0.0081 (18)	0.0092 (19)	0.0080 (18)
C39	0.092 (4)	0.040 (3)	0.061 (3)	−0.008 (2)	−0.032 (3)	0.011 (2)
Cu1	0.0321 (3)	0.0276 (2)	0.0454 (3)	0.00527 (19)	−0.0097 (2)	−0.0091 (2)
Cu2	0.0314 (2)	0.0257 (2)	0.0391 (3)	0.00473 (19)	−0.0119 (2)	−0.00869 (19)
Cu3	0.0420 (3)	0.0264 (2)	0.0397 (3)	0.0055 (2)	−0.0169 (2)	−0.0087 (2)
Cu4	0.0306 (2)	0.0260 (2)	0.0362 (3)	0.00506 (19)	−0.0107 (2)	−0.00862 (19)
N1	0.0262 (16)	0.0268 (16)	0.0302 (17)	0.0048 (13)	0.0002 (13)	−0.0047 (13)
N2	0.0308 (17)	0.0330 (17)	0.0336 (17)	−0.0093 (14)	−0.0085 (14)	−0.0054 (13)
N4	0.0287 (17)	0.0357 (18)	0.0201 (17)	0.0039 (14)	−0.0083 (14)	0.0086 (14)
N5	0.0287 (17)	0.0333 (17)	0.0191 (16)	−0.0197 (14)	0.0045 (13)	−0.0074 (13)
O1	0.0347 (15)	0.0306 (14)	0.0428 (16)	0.0043 (12)	0.0070 (12)	−0.0083 (11)
O2	0.0305 (14)	0.0271 (13)	0.0447 (16)	−0.0050 (11)	−0.0102 (12)	−0.0086 (11)
O3	0.0308 (14)	0.0267 (13)	0.0415 (15)	−0.0025 (11)	−0.0108 (12)	−0.0083 (11)
O4	0.0319 (14)	0.0306 (14)	0.0460 (16)	−0.0064 (11)	−0.0124 (13)	−0.0069 (12)
O5	0.0324 (14)	0.0307 (14)	0.0404 (15)	−0.0081 (11)	−0.0140 (12)	0.0088 (11)
O6	0.0421 (15)	0.0284 (14)	0.0424 (16)	−0.0055 (12)	−0.0197 (13)	−0.0047 (11)
O7	0.0351 (14)	0.0278 (13)	0.0388 (15)	−0.0100 (11)	−0.0138 (12)	0.0059 (11)
O8	0.0323 (14)	0.0222 (13)	0.0422 (15)	−0.0048 (11)	−0.0093 (12)	0.0034 (11)
O9	0.0370 (15)	0.0261 (13)	0.0430 (16)	0.0087 (11)	−0.0161 (13)	−0.0100 (11)
O10	0.0302 (13)	0.0286 (13)	0.0381 (15)	0.0025 (11)	−0.0142 (12)	−0.0085 (11)
O11	0.0334 (14)	0.0263 (13)	0.0406 (15)	0.0038 (11)	−0.0116 (12)	−0.0105 (11)
O12	0.0293 (13)	0.0291 (13)	0.0346 (14)	0.0015 (11)	−0.0072 (11)	0.0010 (11)
O13	0.0389 (15)	0.0444 (16)	0.0398 (15)	0.0103 (13)	−0.0052 (13)	−0.0122 (12)
N3	0.035	0.025	0.039	0.001	0.010	0.006
O14	0.0259 (14)	0.0526 (17)	0.0470 (17)	0.0060 (12)	−0.0092 (13)	−0.0144 (13)
O15	0.0375 (15)	0.0442 (16)	0.0355 (15)	0.0059 (12)	0.0068 (12)	−0.0130 (12)
O16	0.0387 (15)	0.0380 (15)	0.0397 (16)	0.0034 (13)	−0.0094 (13)	−0.0085 (12)
O17	0.0470 (18)	0.0542 (18)	0.0378 (16)	0.0127 (14)	0.0080 (14)	0.0078 (13)
O18	0.0436 (16)	0.0346 (15)	0.0349 (15)	−0.0094 (12)	0.0033 (13)	0.0044 (12)
O19	0.076 (2)	0.0297 (15)	0.0496 (17)	0.0094 (14)	−0.0333 (16)	−0.0077 (12)
O20	0.0410 (16)	0.0478 (17)	0.0567 (19)	−0.0101 (13)	−0.0090 (15)	−0.0153 (14)
O21	0.0410 (17)	0.0404 (17)	0.0619 (19)	−0.0083 (14)	−0.0097 (15)	0.0053 (14)
O22	0.0434 (16)	0.0565 (18)	0.0414 (17)	−0.0136 (14)	0.0076 (13)	−0.0143 (14)
O1W	0.0507 (17)	0.0348 (15)	0.0454 (17)	0.0033 (13)	0.0047 (14)	−0.0102 (12)

Geometric parameters (Å, º) top

Br1—Cu2	2.6994 (6)	C28—H28A	0.9700
Br1—Cu3ⁱ	2.8009 (7)	C28—H28B	0.9700
C1—C2	1.371 (5)	C29—N2	1.521 (4)
C1—C6	1.397 (5)	C29—H29A	0.9700
C1—C7	1.499 (5)	C29—H29B	0.9700
C2—C3	1.397 (5)	C30—N2	1.501 (4)
C2—H2	0.9300	C30—C31	1.517 (5)
C3—C4	1.402 (5)	C30—H30A	0.9700
C3—C8	1.511 (5)	C30—H30B	0.9700
C4—C5	1.399 (5)	C31—C32	1.535 (5)
C4—H4	0.9300	C31—H31A	0.9700
C5—O5	1.373 (4)	C31—H31B	0.9700
C5—C6	1.393 (5)	C32—H32A	0.9600
C6—H6	0.9300	C32—H32B	0.9600
C7—O2	1.241 (4)	C32—H32C	0.9600
C7—O1	1.249 (4)	C33—N2	1.502 (4)
C8—O4	1.245 (4)	C33—C34	1.514 (5)
C8—O3	1.260 (4)	C33—H33A	0.9700
C9—C14	1.394 (5)	C33—H33B	0.9700
C9—C10	1.394 (4)	C34—C35	1.531 (5)
C9—C15	1.493 (5)	C34—H34A	0.9700
C10—C11	1.388 (5)	C34—H34B	0.9700
C10—H10	0.9300	C35—H35A	0.9600
C11—C12	1.388 (5)	C35—H35B	0.9600
C11—C16	1.489 (5)	C35—H35C	0.9600
C12—C13	1.372 (5)	C36—N2	1.514 (4)
C12—H12	0.9300	C36—C37	1.527 (5)
C13—O10	1.377 (4)	C36—H36A	0.9700
C13—C14	1.403 (5)	C36—H36B	0.9700
C14—H14	0.9300	C37—C38	1.523 (5)
C15—O6	1.249 (4)	C37—H37A	0.9700
C15—O7	1.256 (4)	C37—H37B	0.9700
C16—O9	1.257 (4)	C38—H38A	0.9600
C16—O8	1.260 (4)	C38—H38B	0.9600
C17—O5	1.437 (4)	C38—H38C	0.9600
C17—C18	1.507 (5)	C39—O19	1.501 (5)
C17—H17A	0.9700	C39—H39A	0.9600
C17—H17B	0.9700	C39—H39B	0.9600
C18—N1	1.519 (4)	C39—H39C	0.9600
C18—H18A	0.9700	Cu1—O11	1.946 (2)
C18—H18B	0.9700	Cu1—O4ⁱ	1.950 (2)
C19—C20	1.504 (5)	Cu1—O1	1.970 (2)
C19—N1	1.522 (4)	Cu1—O15	2.023 (3)
C19—H19A	0.9700	Cu1—O1W	2.229 (2)
C19—H19B	0.9700	Cu2—O2	1.937 (2)
C20—C21	1.535 (5)	Cu2—O8	1.947 (2)
C20—H20A	0.9700	Cu2—O12ⁱ	1.979 (2)
C20—H20B	0.9700	Cu2—O11	1.986 (2)
C21—H21A	0.9600	Cu2—Cu4ⁱ	2.9300 (7)
C21—H21B	0.9600	Cu3—O6	1.911 (2)
C21—H21C	0.9600	Cu3—O9ⁱⁱ	1.930 (2)
C22—N1	1.496 (4)	Cu3—O12	1.937 (2)
C22—C23	1.503 (5)	Cu3—O19	1.942 (2)
C22—H22A	0.9700	Cu4—O3	1.940 (2)
C22—H22B	0.9700	Cu4—O7	1.957 (2)
C23—C24	1.529 (5)	Cu4—O11ⁱⁱ	1.979 (2)
C23—H23A	0.9700	Cu4—O12	1.988 (2)
C23—H23B	0.9700	Cu4—O18	2.305 (2)
C24—H24A	0.9600	N4—O17	1.244 (4)
C24—H24B	0.9600	N4—O16	1.250 (4)
C24—H24C	0.9600	N4—O18	1.258 (4)
C25—N1	1.512 (4)	N5—O21	1.213 (4)
C25—C26	1.538 (5)	N5—O22	1.256 (4)
C25—H25A	0.9700	N5—O20	1.256 (4)
C25—H25B	0.9700	O11—H11A	0.8499
C26—C27	1.516 (5)	O12—H12B	0.8501
C26—H26A	0.9700	O13—N3	1.260 (4)
C26—H26B	0.9700	N3—O14	1.251 (4)
C27—H27A	0.9600	N3—O15	1.251 (4)
C27—H27B	0.9600	O19—H19	0.8500
C27—H27C	0.9600	O1W—H1Y	0.8501
C28—O10	1.440 (4)	O1W—H1X	0.8500
C28—C29	1.488 (5)

Cu2—Br1—Cu3ⁱ	70.719 (16)	H32B—C32—H32C	109.5
C2—C1—C6	121.0 (3)	N2—C33—C34	116.5 (3)
C2—C1—C7	121.0 (3)	N2—C33—H33A	108.2
C6—C1—C7	118.0 (3)	C34—C33—H33A	108.2
C1—C2—C3	119.0 (3)	N2—C33—H33B	108.2
C1—C2—H2	120.5	C34—C33—H33B	108.2
C3—C2—H2	120.5	H33A—C33—H33B	107.3
C2—C3—C4	121.6 (3)	C33—C34—C35	111.7 (3)
C2—C3—C8	119.4 (3)	C33—C34—H34A	109.3
C4—C3—C8	119.0 (3)	C35—C34—H34A	109.3
C5—C4—C3	118.1 (3)	C33—C34—H34B	109.3
C5—C4—H4	120.9	C35—C34—H34B	109.3
C3—C4—H4	120.9	H34A—C34—H34B	107.9
O5—C5—C6	114.9 (3)	C34—C35—H35A	109.5
O5—C5—C4	124.5 (3)	C34—C35—H35B	109.5
C6—C5—C4	120.6 (3)	H35A—C35—H35B	109.5
C5—C6—C1	119.6 (3)	C34—C35—H35C	109.5
C5—C6—H6	120.2	H35A—C35—H35C	109.5
C1—C6—H6	120.2	H35B—C35—H35C	109.5
O2—C7—O1	126.0 (3)	N2—C36—C37	116.4 (3)
O2—C7—C1	117.8 (3)	N2—C36—H36A	108.2
O1—C7—C1	116.1 (3)	C37—C36—H36A	108.2
O4—C8—O3	127.3 (3)	N2—C36—H36B	108.2
O4—C8—C3	116.0 (3)	C37—C36—H36B	108.2
O3—C8—C3	116.7 (3)	H36A—C36—H36B	107.3
C14—C9—C10	120.4 (3)	C38—C37—C36	110.5 (3)
C14—C9—C15	118.8 (3)	C38—C37—H37A	109.6
C10—C9—C15	120.8 (3)	C36—C37—H37A	109.6
C11—C10—C9	119.2 (3)	C38—C37—H37B	109.6
C11—C10—H10	120.4	C36—C37—H37B	109.6
C9—C10—H10	120.4	H37A—C37—H37B	108.1
C12—C11—C10	120.7 (3)	C37—C38—H38A	109.5
C12—C11—C16	119.1 (3)	C37—C38—H38B	109.5
C10—C11—C16	120.2 (3)	H38A—C38—H38B	109.5
C13—C12—C11	120.0 (3)	C37—C38—H38C	109.5
C13—C12—H12	120.0	H38A—C38—H38C	109.5
C11—C12—H12	120.0	H38B—C38—H38C	109.5
C12—C13—O10	116.7 (3)	O19—C39—H39A	109.5
C12—C13—C14	120.5 (3)	O19—C39—H39B	109.5
O10—C13—C14	122.9 (3)	H39A—C39—H39B	109.5
C9—C14—C13	119.1 (3)	O19—C39—H39C	109.5
C9—C14—H14	120.4	H39A—C39—H39C	109.5
C13—C14—H14	120.4	H39B—C39—H39C	109.5
O6—C15—O7	126.3 (3)	O11—Cu1—O4ⁱ	91.71 (10)
O6—C15—C9	116.6 (3)	O11—Cu1—O1	93.74 (10)
O7—C15—C9	116.9 (3)	O4ⁱ—Cu1—O1	165.90 (10)
O9—C16—O8	127.2 (3)	O11—Cu1—O15	170.94 (10)
O9—C16—C11	115.7 (3)	O4ⁱ—Cu1—O15	86.94 (10)
O8—C16—C11	117.1 (3)	O1—Cu1—O15	85.63 (10)
O5—C17—C18	107.3 (3)	O11—Cu1—O1W	102.00 (10)
O5—C17—H17A	110.3	O4ⁱ—Cu1—O1W	93.16 (10)
C18—C17—H17A	110.3	O1—Cu1—O1W	98.39 (10)
O5—C17—H17B	110.3	O15—Cu1—O1W	87.03 (10)
C18—C17—H17B	110.3	O2—Cu2—O8	83.53 (10)
H17A—C17—H17B	108.5	O2—Cu2—O12ⁱ	167.24 (11)
C17—C18—N1	116.2 (3)	O8—Cu2—O12ⁱ	96.18 (9)
C17—C18—H18A	108.2	O2—Cu2—O11	95.31 (10)
N1—C18—H18A	108.2	O8—Cu2—O11	165.71 (10)
C17—C18—H18B	108.2	O12ⁱ—Cu2—O11	81.81 (9)
N1—C18—H18B	108.2	O2—Cu2—Br1	112.04 (8)
H18A—C18—H18B	107.4	O8—Cu2—Br1	99.64 (7)
C20—C19—N1	117.4 (3)	O12ⁱ—Cu2—Br1	80.63 (7)
C20—C19—H19A	108.0	O11—Cu2—Br1	94.01 (7)
N1—C19—H19A	108.0	O2—Cu2—Cu4ⁱ	137.27 (7)
C20—C19—H19B	108.0	O8—Cu2—Cu4ⁱ	138.55 (7)
N1—C19—H19B	108.0	O12ⁱ—Cu2—Cu4ⁱ	42.51 (6)
H19A—C19—H19B	107.2	O11—Cu2—Cu4ⁱ	42.26 (7)
C19—C20—C21	110.6 (3)	Br1—Cu2—Cu4ⁱ	74.454 (16)
C19—C20—H20A	109.5	O6—Cu3—O9ⁱⁱ	150.80 (11)
C21—C20—H20A	109.5	O6—Cu3—O12	95.66 (10)
C19—C20—H20B	109.5	O9ⁱⁱ—Cu3—O12	96.06 (10)
C21—C20—H20B	109.5	O6—Cu3—O19	81.80 (10)
H20A—C20—H20B	108.1	O9ⁱⁱ—Cu3—O19	85.99 (10)
C20—C21—H21A	109.5	O12—Cu3—O19	177.41 (11)
C20—C21—H21B	109.5	O6—Cu3—Br1ⁱⁱ	113.09 (8)
H21A—C21—H21B	109.5	O9ⁱⁱ—Cu3—Br1ⁱⁱ	95.42 (8)
C20—C21—H21C	109.5	O12—Cu3—Br1ⁱⁱ	78.67 (7)
H21A—C21—H21C	109.5	O19—Cu3—Br1ⁱⁱ	102.75 (9)
H21B—C21—H21C	109.5	O3—Cu4—O7	84.65 (10)
N1—C22—C23	116.5 (3)	O3—Cu4—O11ⁱⁱ	96.59 (9)
N1—C22—H22A	108.2	O7—Cu4—O11ⁱⁱ	175.88 (10)
C23—C22—H22A	108.2	O3—Cu4—O12	177.00 (10)
N1—C22—H22B	108.2	O7—Cu4—O12	96.81 (10)
C23—C22—H22B	108.2	O11ⁱⁱ—Cu4—O12	81.78 (9)
H22A—C22—H22B	107.3	O3—Cu4—O18	92.22 (10)
C22—C23—C24	112.1 (3)	O7—Cu4—O18	91.32 (10)
C22—C23—H23A	109.2	O11ⁱⁱ—Cu4—O18	92.55 (10)
C24—C23—H23A	109.2	O12—Cu4—O18	90.36 (9)
C22—C23—H23B	109.2	O3—Cu4—Cu2ⁱⁱ	135.35 (7)
C24—C23—H23B	109.2	O7—Cu4—Cu2ⁱⁱ	134.90 (7)
H23A—C23—H23B	107.9	O11ⁱⁱ—Cu4—Cu2ⁱⁱ	42.46 (6)
C23—C24—H24A	109.5	O12—Cu4—Cu2ⁱⁱ	42.28 (7)
C23—C24—H24B	109.5	O18—Cu4—Cu2ⁱⁱ	104.16 (6)
H24A—C24—H24B	109.5	C22—N1—C25	109.8 (3)
C23—C24—H24C	109.5	C22—N1—C18	106.5 (3)
H24A—C24—H24C	109.5	C25—N1—C18	112.2 (3)
H24B—C24—H24C	109.5	C22—N1—C19	111.9 (3)
N1—C25—C26	116.9 (3)	C25—N1—C19	106.8 (3)
N1—C25—H25A	108.1	C18—N1—C19	109.7 (3)
C26—C25—H25A	108.1	C30—N2—C33	111.2 (3)
N1—C25—H25B	108.1	C30—N2—C36	105.7 (3)
C26—C25—H25B	108.1	C33—N2—C36	111.8 (3)
H25A—C25—H25B	107.3	C30—N2—C29	110.2 (3)
C27—C26—C25	109.1 (3)	C33—N2—C29	106.5 (3)
C27—C26—H26A	109.9	C36—N2—C29	111.5 (3)
C25—C26—H26A	109.9	O17—N4—O16	121.2 (3)
C27—C26—H26B	109.9	O17—N4—O18	119.8 (3)
C25—C26—H26B	109.9	O16—N4—O18	118.9 (3)
H26A—C26—H26B	108.3	O21—N5—O22	125.2 (3)
C26—C27—H27A	109.5	O21—N5—O20	119.8 (3)
C26—C27—H27B	109.5	O22—N5—O20	114.6 (3)
H27A—C27—H27B	109.5	C7—O1—Cu1	134.1 (2)
C26—C27—H27C	109.5	C7—O2—Cu2	128.9 (2)
H27A—C27—H27C	109.5	C8—O3—Cu4	131.8 (2)
H27B—C27—H27C	109.5	C8—O4—Cu1ⁱⁱ	127.8 (2)
O10—C28—C29	108.1 (3)	C5—O5—C17	120.8 (3)
O10—C28—H28A	110.1	C15—O6—Cu3	134.3 (2)
C29—C28—H28A	110.1	C15—O7—Cu4	130.7 (2)
O10—C28—H28B	110.1	C16—O8—Cu2	128.2 (2)
C29—C28—H28B	110.1	C16—O9—Cu3ⁱ	132.1 (2)
H28A—C28—H28B	108.4	C13—O10—C28	118.3 (3)
C28—C29—N2	118.8 (3)	Cu1—O11—Cu4ⁱ	119.97 (11)
C28—C29—H29A	107.6	Cu1—O11—Cu2	121.16 (13)
N2—C29—H29A	107.6	Cu4ⁱ—O11—Cu2	95.27 (10)
C28—C29—H29B	107.6	Cu1—O11—H11A	106.3
N2—C29—H29B	107.6	Cu4ⁱ—O11—H11A	106.3
H29A—C29—H29B	107.1	Cu2—O11—H11A	106.3
N2—C30—C31	116.9 (3)	Cu3—O12—Cu2ⁱⁱ	108.78 (11)
N2—C30—H30A	108.1	Cu3—O12—Cu4	115.23 (12)
C31—C30—H30A	108.1	Cu2ⁱⁱ—O12—Cu4	95.21 (10)
N2—C30—H30B	108.1	Cu3—O12—H12B	112.2
C31—C30—H30B	108.1	Cu2ⁱⁱ—O12—H12B	112.1
H30A—C30—H30B	107.3	Cu4—O12—H12B	112.1
C30—C31—C32	108.4 (3)	O14—N3—O15	123.0 (3)
C30—C31—H31A	110.0	O14—N3—O13	116.8 (3)
C32—C31—H31A	110.0	O15—N3—O13	120.0 (3)
C30—C31—H31B	110.0	N3—O15—Cu1	103.8 (2)
C32—C31—H31B	110.0	N4—O18—Cu4	125.4 (2)
H31A—C31—H31B	108.4	C39—O19—Cu3	129.2 (2)
C31—C32—H32A	109.5	C39—O19—H19	115.4
C31—C32—H32B	109.5	Cu3—O19—H19	115.4
H32A—C32—H32B	109.5	Cu1—O1W—H1Y	109.3
C31—C32—H32C	109.5	Cu1—O1W—H1X	109.3
H32A—C32—H32C	109.5	H1Y—O1W—H1X	109.5

C6—C1—C2—C3	−0.2 (6)	C23—C22—N1—C18	177.5 (3)
C7—C1—C2—C3	180.0 (3)	C23—C22—N1—C19	57.6 (4)
C1—C2—C3—C4	−1.8 (6)	C26—C25—N1—C22	−49.0 (4)
C1—C2—C3—C8	178.1 (3)	C26—C25—N1—C18	69.2 (4)
C2—C3—C4—C5	1.7 (5)	C26—C25—N1—C19	−170.5 (3)
C8—C3—C4—C5	−178.2 (3)	C17—C18—N1—C22	163.6 (3)
C3—C4—C5—O5	179.8 (3)	C17—C18—N1—C25	43.4 (4)
C3—C4—C5—C6	0.4 (5)	C17—C18—N1—C19	−75.1 (4)
O5—C5—C6—C1	178.2 (3)	C20—C19—N1—C22	48.5 (4)
C4—C5—C6—C1	−2.4 (6)	C20—C19—N1—C25	168.6 (3)
C2—C1—C6—C5	2.3 (6)	C20—C19—N1—C18	−69.6 (4)
C7—C1—C6—C5	−177.9 (3)	C31—C30—N2—C33	−52.6 (4)
C2—C1—C7—O2	−21.3 (5)	C31—C30—N2—C36	−174.2 (3)
C6—C1—C7—O2	158.8 (3)	C31—C30—N2—C29	65.3 (4)
C2—C1—C7—O1	156.5 (3)	C34—C33—N2—C30	−57.6 (4)
C6—C1—C7—O1	−23.4 (5)	C34—C33—N2—C36	60.3 (4)
C2—C3—C8—O4	178.5 (3)	C34—C33—N2—C29	−177.7 (3)
C4—C3—C8—O4	−1.5 (5)	C37—C36—N2—C30	178.9 (3)
C2—C3—C8—O3	−0.3 (5)	C37—C36—N2—C33	57.7 (4)
C4—C3—C8—O3	179.7 (3)	C37—C36—N2—C29	−61.3 (4)
C14—C9—C10—C11	3.9 (5)	C28—C29—N2—C30	57.0 (4)
C15—C9—C10—C11	−177.8 (3)	C28—C29—N2—C33	177.8 (3)
C9—C10—C11—C12	−4.7 (5)	C28—C29—N2—C36	−60.0 (4)
C9—C10—C11—C16	178.6 (3)	O2—C7—O1—Cu1	−36.9 (6)
C10—C11—C12—C13	2.1 (6)	C1—C7—O1—Cu1	145.5 (3)
C16—C11—C12—C13	178.9 (3)	O1—C7—O2—Cu2	2.5 (6)
C11—C12—C13—O10	−179.5 (3)	C1—C7—O2—Cu2	−179.9 (2)
C11—C12—C13—C14	1.3 (6)	O4—C8—O3—Cu4	−12.0 (6)
C10—C9—C14—C13	−0.5 (5)	C3—C8—O3—Cu4	166.6 (2)
C15—C9—C14—C13	−178.9 (3)	O3—C8—O4—Cu1ⁱⁱ	−27.8 (6)
C12—C13—C14—C9	−2.1 (5)	C3—C8—O4—Cu1ⁱⁱ	153.6 (2)
O10—C13—C14—C9	178.8 (3)	C6—C5—O5—C17	165.6 (3)
C14—C9—C15—O6	−15.4 (5)	C4—C5—O5—C17	−13.9 (5)
C10—C9—C15—O6	166.3 (3)	C18—C17—O5—C5	−159.1 (3)
C14—C9—C15—O7	170.0 (3)	O7—C15—O6—Cu3	−9.0 (6)
C10—C9—C15—O7	−8.4 (5)	C9—C15—O6—Cu3	176.9 (2)
C12—C11—C16—O9	18.9 (5)	O6—C15—O7—Cu4	15.5 (6)
C10—C11—C16—O9	−164.3 (3)	C9—C15—O7—Cu4	−170.4 (2)
C12—C11—C16—O8	−163.7 (3)	O9—C16—O8—Cu2	8.6 (6)
C10—C11—C16—O8	13.1 (5)	C11—C16—O8—Cu2	−168.4 (2)
O5—C17—C18—N1	−84.5 (4)	O8—C16—O9—Cu3ⁱ	−4.7 (6)
N1—C19—C20—C21	−173.6 (3)	C11—C16—O9—Cu3ⁱ	172.4 (2)
N1—C22—C23—C24	−174.3 (3)	C12—C13—O10—C28	170.6 (3)
N1—C25—C26—C27	−171.0 (3)	C14—C13—O10—C28	−10.3 (5)
O10—C28—C29—N2	−82.6 (4)	C29—C28—O10—C13	−169.9 (3)
N2—C30—C31—C32	−177.0 (3)	O14—N3—O15—Cu1	−174.4 (3)
N2—C33—C34—C35	173.4 (3)	O13—N3—O15—Cu1	0.1 (3)
N2—C36—C37—C38	173.4 (3)	O17—N4—O18—Cu4	163.9 (2)
C23—C22—N1—C25	−60.8 (4)	O16—N4—O18—Cu4	−20.5 (4)

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

Poly[µ₃-bromido-µ₂-bromido-bromido-µ₃-hydroxido-{µ₄-5-[2-(tripropylazaniumyl)ethoxy]benzene-1,3-dicarboxylato}tricopper(II)] (2) top

Crystal data top

[Cu₃Br₃(C₁₉H₂₈NO₅)(OH)]	F(000) = 1560
M_r = 797.78	D_x = 2.058 Mg m⁻³
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.0572 (7) Å	Cell parameters from 2591 reflections
b = 10.6773 (8) Å	θ = 2.3–25.0°
c = 26.743 (2) Å	µ = 7.15 mm⁻¹
β = 95.505 (3)°	T = 296 K
V = 2574.3 (4) Å³	Block, blue
Z = 4	0.24 × 0.22 × 0.20 mm

Data collection top

Bruker D8 diffractometer	4679 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.049
ω rotation scans	θ_max = 27.6°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2015)	h = −11→9
T_min = 0.3, T_max = 0.33	k = −13→12
21720 measured reflections	l = −34→26
5829 independent reflections

Refinement top

Refinement on F²	4 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.03P)²] where P = (F_o² + 2F_c²)/3
S = 1.45	(Δ/σ)_max = 0.001
5829 reflections	Δρ_max = 0.92 e Å⁻³
293 parameters	Δρ_min = −0.85 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.49074 (5)	0.70580 (4)	0.33094 (2)	0.04541 (13)
Br2	0.76974 (5)	0.54985 (4)	0.42784 (2)	0.04482 (13)
Br3	0.94983 (5)	0.84742 (4)	0.37787 (2)	0.04260 (12)
C1	0.5677 (4)	0.3873 (3)	0.20284 (15)	0.0295 (8)
C2	0.4955 (4)	0.2816 (3)	0.21317 (16)	0.0353 (9)
H2	0.403807	0.285585	0.226058	0.042*
C3	0.5610 (4)	0.1638 (3)	0.20417 (17)	0.0371 (10)
C4	0.7003 (5)	0.1551 (4)	0.18775 (16)	0.0389 (10)
H4	0.744870	0.078130	0.182947	0.047*
C5	0.7717 (5)	0.2687 (4)	0.17863 (16)	0.0393 (10)
C6	0.7110 (4)	0.3813 (4)	0.18600 (16)	0.0372 (10)
H6	0.762543	0.454337	0.180121	0.045*
C7	0.4990 (4)	0.5118 (3)	0.21394 (16)	0.0352 (9)
C8	0.4835 (5)	0.0482 (4)	0.22022 (17)	0.0383 (10)
C9	1.0009 (4)	0.3587 (3)	0.15639 (16)	0.0371 (10)
H9A	1.009783	0.406106	0.187466	0.045*
H9B	0.957392	0.412369	0.129664	0.045*
C10	1.1503 (4)	0.3139 (4)	0.14459 (17)	0.0399 (10)
H10A	1.171253	0.235492	0.162188	0.048*
H10B	1.223805	0.374200	0.158010	0.048*
C11	1.0520 (5)	0.2029 (3)	0.06514 (18)	0.0406 (10)
H11A	0.954489	0.236011	0.069670	0.049*
H11B	1.060596	0.196880	0.029343	0.049*
C12	1.0671 (4)	0.0721 (3)	0.08840 (17)	0.0380 (10)
H12A	1.073624	0.077623	0.124748	0.046*
H12B	1.155796	0.031290	0.078847	0.046*
C13	0.9280 (4)	−0.0024 (3)	0.06848 (16)	0.0417 (11)
H13A	0.848885	0.054719	0.058314	0.063*
H13B	0.898544	−0.056186	0.094502	0.063*
H13C	0.949987	−0.052040	0.040202	0.063*
C14	1.1482 (4)	0.4192 (3)	0.06235 (17)	0.0401 (10)
H14A	1.149273	0.405516	0.026524	0.048*
H14B	1.050371	0.450061	0.067894	0.048*
C15	1.2596 (5)	0.5199 (4)	0.07801 (17)	0.0441 (11)
H15A	1.358590	0.491897	0.072460	0.053*
H15B	1.257691	0.538243	0.113465	0.053*
C16	1.2199 (5)	0.6369 (4)	0.04691 (17)	0.0434 (11)
H16A	1.159748	0.613956	0.016781	0.065*
H16B	1.309061	0.676634	0.038258	0.065*
H16C	1.165796	0.693905	0.066103	0.065*
C17	1.3255 (4)	0.2456 (4)	0.08675 (17)	0.0392 (10)
H17A	1.339058	0.172071	0.107980	0.047*
H17B	1.394549	0.309058	0.100526	0.047*
C18	1.3636 (5)	0.2121 (4)	0.03482 (17)	0.0398 (10)
H18A	1.349824	0.284272	0.012847	0.048*
H18B	1.299269	0.145429	0.021050	0.048*
C19	1.5272 (4)	0.1689 (4)	0.03840 (17)	0.0426 (11)
H19A	1.589079	0.231609	0.055440	0.064*
H19B	1.556656	0.156507	0.005216	0.064*
H19C	1.537459	0.091608	0.056775	0.064*
Cu1	0.55567 (5)	0.77831 (4)	0.23297 (2)	0.03907 (14)
Cu2	0.250000	0.63912 (6)	0.250000	0.03780 (18)
Cu3	0.74211 (6)	0.71128 (5)	0.36184 (2)	0.04386 (15)
Cu4	0.250000	−0.08429 (6)	0.250000	0.03787 (18)
N1	1.1706 (4)	0.2934 (3)	0.08878 (14)	0.0372 (8)
O1	0.5823 (3)	0.6057 (2)	0.21601 (11)	0.0415 (7)
O2	0.3667 (3)	0.5103 (2)	0.22349 (11)	0.0372 (7)
O3	0.3445 (3)	0.0454 (2)	0.21498 (11)	0.0388 (7)
O4	0.5639 (3)	−0.0380 (2)	0.24054 (11)	0.0409 (7)
O5	0.9105 (3)	0.2516 (2)	0.16114 (11)	0.0382 (7)
O6	0.3445 (3)	0.7793 (2)	0.21613 (11)	0.0379 (7)
H1X	0.305681	0.772498	0.186020	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0431 (3)	0.0401 (2)	0.0495 (3)	0.01136 (18)	−0.0140 (2)	−0.01142 (19)
Br2	0.0409 (3)	0.0503 (3)	0.0446 (3)	−0.01324 (19)	0.0109 (2)	−0.0137 (2)
Br3	0.0422 (3)	0.0386 (2)	0.0483 (3)	0.00901 (18)	0.0109 (2)	0.00948 (19)
C1	0.033 (2)	0.0138 (14)	0.038 (2)	0.0000 (11)	−0.0139 (17)	−0.0040 (13)
C2	0.032 (2)	0.0234 (14)	0.049 (3)	0.0034 (14)	−0.0067 (18)	0.0106 (16)
C3	0.035 (2)	0.031 (2)	0.047 (3)	−0.0116 (17)	0.0105 (19)	−0.0082 (18)
C4	0.038 (2)	0.036 (2)	0.045 (3)	−0.0121 (18)	0.0138 (19)	−0.0112 (18)
C5	0.039 (3)	0.040 (2)	0.041 (3)	0.0151 (18)	0.014 (2)	0.0099 (18)
C6	0.037 (2)	0.032 (2)	0.043 (3)	−0.0074 (17)	0.0061 (19)	0.0115 (17)
C7	0.035 (2)	0.0226 (13)	0.050 (3)	0.0005 (15)	0.0138 (19)	0.0053 (16)
C8	0.037 (3)	0.032 (2)	0.047 (3)	−0.0095 (18)	0.011 (2)	−0.0101 (18)
C9	0.034 (2)	0.036 (2)	0.043 (3)	0.0074 (17)	0.0105 (18)	0.0110 (17)
C10	0.037 (2)	0.042 (2)	0.041 (3)	−0.0085 (18)	0.0085 (19)	0.0110 (19)
C11	0.037 (2)	0.038 (2)	0.045 (3)	−0.0053 (16)	−0.0032 (18)	0.0114 (18)
C12	0.037 (2)	0.035 (2)	0.043 (3)	0.0086 (17)	0.0073 (19)	−0.0080 (18)
C13	0.042 (3)	0.034 (2)	0.047 (3)	−0.0126 (19)	−0.008 (2)	−0.0108 (19)
C14	0.038 (2)	0.041 (2)	0.043 (3)	−0.0157 (18)	0.0075 (19)	0.0090 (18)
C15	0.044 (3)	0.044 (3)	0.046 (3)	−0.011 (2)	0.013 (2)	0.014 (2)
C16	0.045 (3)	0.036 (2)	0.047 (3)	−0.0149 (19)	−0.010 (2)	0.0121 (19)
C17	0.036 (2)	0.036 (2)	0.047 (3)	0.0090 (18)	0.0104 (19)	0.0114 (18)
C18	0.040 (2)	0.039 (2)	0.042 (3)	0.0141 (18)	0.012 (2)	0.0095 (18)
C19	0.042 (3)	0.036 (2)	0.051 (3)	0.0136 (19)	0.009 (2)	−0.0058 (19)
Cu1	0.0360 (3)	0.0338 (3)	0.0485 (4)	−0.0089 (2)	0.0098 (2)	0.0090 (2)
Cu2	0.0364 (4)	0.0332 (4)	0.0452 (5)	0.000	0.0111 (3)	0.000
Cu3	0.0418 (3)	0.0426 (3)	0.0490 (4)	−0.0109 (2)	0.0135 (3)	−0.0132 (2)
Cu4	0.0366 (4)	0.0330 (4)	0.0453 (5)	0.000	0.0103 (3)	0.000
N1	0.0333 (19)	0.0360 (19)	0.042 (2)	0.0078 (13)	0.0054 (15)	−0.0111 (14)
O1	0.0360 (17)	0.0375 (16)	0.053 (2)	0.0092 (13)	0.0136 (14)	0.0105 (13)
O2	0.0347 (16)	0.0312 (15)	0.0470 (19)	0.0113 (11)	0.0106 (13)	0.0084 (12)
O3	0.0357 (18)	0.0330 (15)	0.0491 (19)	−0.0079 (12)	0.0117 (13)	−0.0084 (12)
O4	0.0356 (16)	0.0353 (16)	0.049 (2)	−0.0100 (12)	−0.0081 (13)	0.0123 (13)
O5	0.0341 (17)	0.0346 (15)	0.0471 (19)	−0.0095 (12)	0.0104 (13)	−0.0105 (12)
O6	0.0347 (16)	0.0373 (16)	0.0423 (19)	0.0093 (12)	0.0077 (13)	−0.0095 (12)

Geometric parameters (Å, º) top

Br1—Cu3	2.3471 (7)	C13—H13B	0.9600
Br1—Cu1	2.8470 (8)	C13—H13C	0.9600
Br2—Cu3	2.4627 (8)	C14—C15	1.506 (5)
Br3—Cu3	2.3836 (7)	C14—N1	1.523 (5)
C1—C2	1.346 (5)	C14—H14A	0.9700
C1—C6	1.416 (5)	C14—H14B	0.9700
C1—C7	1.510 (5)	C15—C16	1.525 (5)
C2—C3	1.421 (5)	C15—H15A	0.9700
C2—H2	0.9300	C15—H15B	0.9700
C3—C4	1.379 (6)	C16—H16A	0.9600
C3—C8	1.502 (5)	C16—H16B	0.9600
C4—C5	1.406 (5)	C16—H16C	0.9600
C4—H4	0.9300	C17—N1	1.499 (5)
C5—C6	1.344 (5)	C17—C18	1.506 (6)
C5—O5	1.395 (5)	C17—H17A	0.9700
C6—H6	0.9300	C17—H17B	0.9700
C7—O1	1.252 (4)	C18—C19	1.546 (5)
C7—O2	1.249 (4)	C18—H18A	0.9700
C8—O3	1.254 (5)	C18—H18B	0.9700
C8—O4	1.264 (5)	C19—H19A	0.9600
C9—O5	1.419 (4)	C19—H19B	0.9600
C9—C10	1.497 (5)	C19—H19C	0.9600
C9—H9A	0.9700	Cu1—O1	1.919 (3)
C9—H9B	0.9700	Cu1—O6	1.923 (3)
C10—N1	1.537 (5)	Cu1—O4ⁱ	1.972 (3)
C10—H10A	0.9700	Cu2—O2ⁱⁱ	1.912 (3)
C10—H10B	0.9700	Cu2—O2	1.912 (3)
C11—C12	1.529 (5)	Cu2—O6ⁱⁱ	1.985 (3)
C11—N1	1.535 (5)	Cu2—O6	1.985 (3)
C11—H11A	0.9700	Cu2—Cu4ⁱ	2.9531 (10)
C11—H11B	0.9700	Cu4—O3ⁱⁱ	1.919 (3)
C12—C13	1.541 (5)	Cu4—O3	1.919 (3)
C12—H12A	0.9700	Cu4—O6ⁱⁱⁱ	1.955 (2)
C12—H12B	0.9700	Cu4—O6^iv	1.955 (2)
C13—H13A	0.9600	O6—H1X	0.8501

Cu3—Br1—Cu1	92.19 (2)	H16A—C16—H16B	109.5
C2—C1—C6	120.4 (3)	C15—C16—H16C	109.5
C2—C1—C7	118.7 (4)	H16A—C16—H16C	109.5
C6—C1—C7	120.7 (3)	H16B—C16—H16C	109.5
C1—C2—C3	119.2 (4)	N1—C17—C18	114.4 (4)
C1—C2—H2	120.4	N1—C17—H17A	108.7
C3—C2—H2	120.4	C18—C17—H17A	108.7
C4—C3—C2	121.5 (4)	N1—C17—H17B	108.7
C4—C3—C8	120.2 (4)	C18—C17—H17B	108.7
C2—C3—C8	117.7 (4)	H17A—C17—H17B	107.6
C3—C4—C5	116.6 (4)	C17—C18—C19	108.5 (4)
C3—C4—H4	121.7	C17—C18—H18A	110.0
C5—C4—H4	121.7	C19—C18—H18A	110.0
C6—C5—O5	124.1 (4)	C17—C18—H18B	110.0
C6—C5—C4	123.0 (4)	C19—C18—H18B	110.0
O5—C5—C4	112.9 (3)	H18A—C18—H18B	108.4
C5—C6—C1	119.2 (3)	C18—C19—H19A	109.5
C5—C6—H6	120.4	C18—C19—H19B	109.5
C1—C6—H6	120.4	H19A—C19—H19B	109.5
O1—C7—O2	126.0 (4)	C18—C19—H19C	109.5
O1—C7—C1	117.1 (3)	H19A—C19—H19C	109.5
O2—C7—C1	116.7 (3)	H19B—C19—H19C	109.5
O3—C8—O4	124.2 (4)	O1—Cu1—O6	95.42 (11)
O3—C8—C3	118.6 (4)	O1—Cu1—O4ⁱ	167.18 (12)
O4—C8—C3	117.1 (4)	O6—Cu1—O4ⁱ	92.61 (10)
O5—C9—C10	107.6 (3)	O1—Cu1—Br1	89.89 (9)
O5—C9—H9A	110.2	O6—Cu1—Br1	85.89 (9)
C10—C9—H9A	110.2	O4ⁱ—Cu1—Br1	100.67 (9)
O5—C9—H9B	110.2	O2ⁱⁱ—Cu2—O2	87.98 (16)
C10—C9—H9B	110.2	O2ⁱⁱ—Cu2—O6ⁱⁱ	95.48 (10)
H9A—C9—H9B	108.5	O2—Cu2—O6ⁱⁱ	171.62 (11)
C9—C10—N1	116.4 (3)	O2ⁱⁱ—Cu2—O6	171.62 (11)
C9—C10—H10A	108.2	O2—Cu2—O6	95.48 (10)
N1—C10—H10A	108.2	O6ⁱⁱ—Cu2—O6	82.15 (14)
C9—C10—H10B	108.2	O2ⁱⁱ—Cu2—Cu4ⁱ	136.01 (8)
N1—C10—H10B	108.2	O2—Cu2—Cu4ⁱ	136.01 (8)
H10A—C10—H10B	107.3	O6ⁱⁱ—Cu2—Cu4ⁱ	41.07 (7)
C12—C11—N1	112.1 (3)	O6—Cu2—Cu4ⁱ	41.07 (7)
C12—C11—H11A	109.2	Br1—Cu3—Br3	143.20 (3)
N1—C11—H11A	109.2	Br1—Cu3—Br2	105.27 (2)
C12—C11—H11B	109.2	Br3—Cu3—Br2	105.88 (3)
N1—C11—H11B	109.2	O3ⁱⁱ—Cu4—O3	87.57 (16)
H11A—C11—H11B	107.9	O3ⁱⁱ—Cu4—O6ⁱⁱⁱ	177.97 (12)
C11—C12—C13	107.0 (3)	O3—Cu4—O6ⁱⁱⁱ	94.38 (11)
C11—C12—H12A	110.3	O3ⁱⁱ—Cu4—O6^iv	94.38 (11)
C13—C12—H12A	110.3	O3—Cu4—O6^iv	177.97 (12)
C11—C12—H12B	110.3	O6ⁱⁱⁱ—Cu4—O6^iv	83.68 (16)
C13—C12—H12B	110.3	O3ⁱⁱ—Cu4—Cu2ⁱⁱⁱ	136.21 (8)
H12A—C12—H12B	108.6	O3—Cu4—Cu2ⁱⁱⁱ	136.21 (8)
C12—C13—H13A	109.5	O6ⁱⁱⁱ—Cu4—Cu2ⁱⁱⁱ	41.84 (8)
C12—C13—H13B	109.5	O6^iv—Cu4—Cu2ⁱⁱⁱ	41.84 (8)
H13A—C13—H13B	109.5	C17—N1—C10	106.5 (3)
C12—C13—H13C	109.5	C17—N1—C14	111.5 (3)
H13A—C13—H13C	109.5	C10—N1—C14	107.6 (3)
H13B—C13—H13C	109.5	C17—N1—C11	113.1 (3)
C15—C14—N1	116.4 (3)	C10—N1—C11	110.2 (3)
C15—C14—H14A	108.2	C14—N1—C11	107.9 (3)
N1—C14—H14A	108.2	C7—O1—Cu1	133.6 (3)
C15—C14—H14B	108.2	C7—O2—Cu2	129.9 (3)
N1—C14—H14B	108.2	C8—O3—Cu4	116.9 (3)
H14A—C14—H14B	107.3	C8—O4—Cu1ⁱⁱⁱ	131.7 (3)
C14—C15—C16	108.5 (4)	C5—O5—C9	118.1 (3)
C14—C15—H15A	110.0	Cu1—O6—Cu4ⁱ	111.42 (13)
C16—C15—H15A	110.0	Cu1—O6—Cu2	110.59 (13)
C14—C15—H15B	110.0	Cu4ⁱ—O6—Cu2	97.09 (12)
C16—C15—H15B	110.0	Cu1—O6—H1X	122.2
H15A—C15—H15B	108.4	Cu4ⁱ—O6—H1X	110.1
C15—C16—H16A	109.5	Cu2—O6—H1X	102.2
C15—C16—H16B	109.5

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Br2^v	0.93	3.05	3.555 (4)	116
C9—H9B···Br2^v	0.97	2.85	3.767 (4)	157
C14—H14B···Br2^v	0.97	3.10	4.066 (4)	173
C10—H10B···O2^vi	0.97	2.53	3.449 (5)	157
C11—H11A···O5	0.97	2.52	3.023 (6)	112
C12—H12A···O5	0.97	2.62	3.161 (5)	116
C14—H14A···Br2^vii	0.97	2.99	3.875 (4)	153
C18—H18A···Br2^vii	0.97	2.92	3.860 (4)	164
O6—H1X···Br1ⁱⁱ	0.85	2.77	3.269 (3)	119
C6—H6···Br2^v	0.93	3.05	3.555 (4)	116
C9—H9B···Br2^v	0.97	2.85	3.767 (4)	157
C10—H10B···O2^vi	0.97	2.53	3.449 (5)	157
C11—H11A···O5	0.97	2.52	3.023 (6)	112
C12—H12A···O5	0.97	2.62	3.161 (5)	116
C14—H14A···Br2^vii	0.97	2.99	3.875 (4)	153
C14—H14B···Br2^v	0.97	3.10	4.066 (4)	173
C18—H18A···Br2^vii	0.97	2.92	3.860 (4)	164
O6—H1X···Br1ⁱⁱ	0.85	2.77	3.269 (3)	119

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

Poly[bromido{µ₃-5-[2-(tripropylazaniumyl)ethoxy]benzene-1,3-dicarboxylato}zinc(II)] (3) top

Crystal data top

[ZnBr(C₁₉H₂₈NO₅)]	F(000) = 1016
M_r = 495.70	D_x = 1.580 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.5479 (7) Å	Cell parameters from 9963 reflections
b = 14.7949 (10) Å	θ = 2.2–34.2°
c = 12.3782 (9) Å	µ = 3.13 mm⁻¹
β = 99.813 (2)°	T = 290 K
V = 2083.9 (2) Å³	Prism, colorless
Z = 4	0.35 × 0.26 × 0.21 mm

Data collection top

Bruker D8 diffractometer	3523 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
phi and ω scans	θ_max = 25.8°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2015)	h = −14→12
T_min = 0.418, T_max = 0.747	k = −18→15
14849 measured reflections	l = −15→15
3966 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0492P)² + 2.801P] where P = (F_o² + 2F_c²)/3
3966 reflections	(Δ/σ)_max = 0.001
247 parameters	Δρ_max = 0.72 e Å⁻³
5 restraints	Δρ_min = −1.25 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O5	0.62771 (16)	0.03422 (12)	0.54057 (16)	0.0263 (4)
C1	0.7629 (2)	−0.05002 (17)	0.6674 (2)	0.0224 (5)
N1	1.16840 (19)	0.24469 (15)	0.80952 (19)	0.0247 (5)
C2	0.8204 (2)	0.02892 (17)	0.7077 (2)	0.0230 (5)
H2	0.793506	0.084924	0.679920	0.028*
C3	0.8987 (3)	−0.13799 (19)	0.7940 (2)	0.0290 (6)
C9	0.9577 (2)	0.18023 (19)	0.7768 (3)	0.0315 (6)
H9A	0.877783	0.198673	0.780298	0.038*
H9B	0.964954	0.173597	0.700304	0.038*
C10	1.0425 (2)	0.25082 (19)	0.8300 (3)	0.0298 (6)
H10A	1.044118	0.248118	0.908518	0.036*
H10B	1.011841	0.309683	0.805254	0.036*
C4	0.8014 (2)	−0.13318 (18)	0.7113 (2)	0.0275 (6)
H4	0.761982	−0.185707	0.685258	0.033*
O1	0.98248 (19)	0.09652 (14)	0.83219 (19)	0.0374 (5)
C5	0.9578 (2)	−0.0601 (2)	0.8324 (2)	0.0298 (6)
H5	1.023901	−0.063376	0.886931	0.036*
C6	0.6606 (2)	−0.04292 (18)	0.5756 (2)	0.0253 (6)
C16	1.2301 (2)	0.1595 (2)	0.8580 (2)	0.0310 (6)
H16A	1.188629	0.107773	0.821950	0.037*
H16B	1.308733	0.158960	0.840231	0.037*
C7	0.9178 (2)	0.02309 (18)	0.7891 (2)	0.0262 (6)
C11	1.1752 (3)	0.2412 (2)	0.6878 (2)	0.0314 (6)
H11A	1.257539	0.239072	0.680621	0.038*
H11B	1.139721	0.184978	0.658536	0.038*
C13	1.2276 (2)	0.3291 (2)	0.8635 (3)	0.0313 (6)
H13A	1.184349	0.381604	0.831575	0.038*
H13B	1.221987	0.327893	0.940759	0.038*
C12	1.1184 (4)	0.3172 (3)	0.6173 (3)	0.0492 (9)
H12A	1.151002	0.374520	0.645730	0.059*
H12B	1.034542	0.317846	0.618245	0.059*
C8	0.9435 (3)	−0.2274 (2)	0.8428 (3)	0.0431 (7)
C14	1.3551 (3)	0.3409 (3)	0.8532 (3)	0.0528 (10)
H14A	1.362331	0.345540	0.776457	0.063*
H14B	1.399997	0.288818	0.884093	0.063*
C17	1.2403 (4)	0.1467 (3)	0.9802 (3)	0.0499 (9)
H17A	1.162833	0.149449	1.000526	0.060*
H17B	1.287675	0.194831	1.018348	0.060*
C15	1.4028 (4)	0.4256 (3)	0.9134 (4)	0.0717 (14)
H15A	1.358855	0.477058	0.881770	0.108*
H15B	1.483990	0.432983	0.907311	0.108*
H15C	1.395652	0.420603	0.989319	0.108*
C18	1.2962 (4)	0.0564 (3)	1.0132 (4)	0.0634 (11)
H18A	1.305587	0.049750	1.091343	0.095*
H18B	1.371736	0.053264	0.990847	0.095*
H18C	1.246893	0.008879	0.978367	0.095*
O4	0.61517 (19)	−0.11582 (13)	0.53639 (19)	0.0377 (5)
O2	0.8730 (3)	−0.29053 (16)	0.8422 (3)	0.0667 (8)
O3	1.0481 (3)	−0.2357 (2)	0.8837 (3)	0.0687 (8)
C20	1.1399 (4)	0.3041 (3)	0.5013 (3)	0.0626 (11)
H20A	1.222957	0.304751	0.500619	0.094*
H20B	1.102976	0.352185	0.455846	0.094*
H20C	1.107624	0.247248	0.473613	0.094*
Zn1	0.99387 (3)	−0.38971 (2)	0.90243 (3)	0.02677 (11)
Br1	1.04286 (3)	−0.46593 (2)	0.74963 (3)	0.04755 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O5	0.0294 (10)	0.0213 (10)	0.0277 (10)	−0.0009 (7)	0.0030 (8)	0.0000 (8)
C1	0.0248 (12)	0.0177 (12)	0.0256 (13)	−0.0010 (10)	0.0065 (10)	−0.0013 (10)
N1	0.0237 (11)	0.0200 (11)	0.0308 (12)	−0.0006 (9)	0.0054 (9)	−0.0061 (9)
C2	0.0246 (12)	0.0143 (12)	0.0291 (14)	0.0004 (9)	0.0023 (10)	0.0027 (10)
C3	0.0367 (15)	0.0191 (13)	0.0341 (15)	0.0079 (11)	0.0147 (12)	0.0092 (11)
C9	0.0235 (13)	0.0201 (13)	0.0485 (18)	0.0001 (10)	−0.0010 (12)	0.0001 (12)
C10	0.0237 (13)	0.0221 (13)	0.0445 (17)	0.0008 (11)	0.0081 (11)	−0.0074 (12)
C4	0.0350 (14)	0.0158 (12)	0.0342 (15)	−0.0020 (10)	0.0127 (11)	0.0002 (11)
O1	0.0366 (11)	0.0248 (10)	0.0441 (13)	−0.0085 (9)	−0.0126 (9)	0.0053 (9)
C5	0.0294 (14)	0.0286 (15)	0.0306 (15)	0.0047 (11)	0.0027 (11)	0.0083 (12)
C6	0.0266 (13)	0.0217 (13)	0.0285 (14)	−0.0042 (10)	0.0072 (10)	−0.0030 (11)
C16	0.0296 (14)	0.0279 (15)	0.0357 (16)	0.0075 (11)	0.0060 (11)	−0.0017 (12)
C7	0.0263 (13)	0.0199 (13)	0.0320 (15)	−0.0030 (10)	0.0041 (11)	0.0026 (11)
C11	0.0365 (15)	0.0295 (15)	0.0284 (15)	0.0004 (12)	0.0062 (11)	−0.0080 (12)
C13	0.0323 (15)	0.0255 (14)	0.0364 (16)	−0.0085 (11)	0.0068 (11)	−0.0117 (12)
C12	0.067 (2)	0.041 (2)	0.0386 (19)	0.0067 (17)	0.0059 (16)	0.0017 (16)
C8	0.0668 (14)	0.0275 (10)	0.0411 (18)	0.0218 (10)	0.0265 (13)	0.0155 (13)
C14	0.0371 (18)	0.061 (2)	0.062 (2)	−0.0222 (17)	0.0148 (16)	−0.025 (2)
C17	0.063 (2)	0.051 (2)	0.0360 (18)	0.0173 (18)	0.0098 (16)	0.0031 (16)
C15	0.064 (3)	0.085 (3)	0.071 (3)	−0.049 (2)	0.024 (2)	−0.038 (3)
C18	0.073 (3)	0.066 (3)	0.051 (2)	0.026 (2)	0.011 (2)	0.021 (2)
O4	0.0424 (12)	0.0218 (10)	0.0437 (13)	−0.0059 (9)	−0.0073 (9)	−0.0079 (9)
O2	0.0800 (14)	0.0218 (11)	0.108 (2)	0.0239 (8)	0.0427 (15)	0.0301 (13)
O3	0.0838 (14)	0.0480 (16)	0.0660 (18)	0.0312 (12)	−0.0107 (15)	0.0171 (14)
C20	0.084 (3)	0.065 (3)	0.0353 (19)	0.000 (2)	0.0013 (18)	0.0042 (19)
Zn1	0.03115 (18)	0.01738 (17)	0.0312 (2)	0.00365 (12)	0.00376 (13)	0.00360 (12)
Br1	0.0651 (2)	0.0404 (2)	0.0419 (2)	0.00433 (16)	0.02288 (16)	−0.00023 (14)

Geometric parameters (Å, º) top

Br1—Zn1	2.3523 (5)	C10—H10A	0.9700
Zn1—O2	2.075 (2)	C10—H10B	0.9700
Zn1—O3	2.385 (3)	C11—H11A	0.9700
Zn1—O4ⁱ	1.982 (2)	C11—H11B	0.9700
Zn1—O5ⁱⁱ	2.0182 (19)	C11—C12	1.504 (5)
Zn1—C8	2.551 (3)	C12—H12A	0.9700
O1—C7	1.374 (3)	C12—H12B	0.9700
O1—C9	1.421 (3)	C12—C20	1.512 (5)
O2—C8	1.239 (5)	C13—H13A	0.9700
O3—C8	1.234 (5)	C13—H13B	0.9700
O4—C6	1.260 (3)	C13—C14	1.509 (4)
O5—C6	1.256 (3)	C14—H14A	0.9700
N1—C10	1.520 (3)	C14—H14B	0.9700
N1—C11	1.523 (4)	C14—C15	1.513 (5)
N1—C13	1.523 (3)	C15—H15A	0.9600
N1—C16	1.521 (4)	C15—H15B	0.9600
C1—C2	1.393 (4)	C15—H15C	0.9600
C1—C4	1.387 (4)	C16—H16A	0.9700
C1—C6	1.496 (4)	C16—H16B	0.9700
C2—H2	0.9300	C16—C17	1.509 (5)
C2—C7	1.379 (4)	C17—H17A	0.9700
C3—C4	1.387 (4)	C17—H17B	0.9700
C3—C5	1.381 (4)	C17—C18	1.510 (5)
C3—C8	1.508 (4)	C18—H18A	0.9600
C4—H4	0.9300	C18—H18B	0.9600
C5—H5	0.9300	C18—H18C	0.9600
C5—C7	1.390 (4)	C20—H20A	0.9600
C9—H9A	0.9700	C20—H20B	0.9600
C9—H9B	0.9700	C20—H20C	0.9600
C9—C10	1.505 (4)

Br1—Zn1—O3	106.07 (8)	N1—C10—H10B	108.0
Br1—Zn1—C8	107.03 (8)	C9—C10—N1	117.1 (2)
O2—Zn1—Br1	106.82 (10)	C9—C10—H10A	108.0
O2—Zn1—O3	57.39 (11)	C9—C10—H10B	108.0
O2—Zn1—C8	28.79 (12)	H10A—C10—H10B	107.3
O3—Zn1—C8	28.71 (11)	N1—C11—H11A	108.0
O4ⁱ—Zn1—Br1	117.39 (7)	N1—C11—H11B	108.0
O4ⁱ—Zn1—O2	127.45 (12)	H11A—C11—H11B	107.2
O4ⁱ—Zn1—O3	83.21 (9)	C12—C11—N1	117.2 (3)
O4ⁱ—Zn1—O5ⁱⁱ	99.50 (9)	C12—C11—H11A	108.0
O4ⁱ—Zn1—C8	107.28 (11)	C12—C11—H11B	108.0
O5ⁱⁱ—Zn1—Br1	106.91 (6)	C11—C12—H12A	109.8
O5ⁱⁱ—Zn1—O2	93.12 (10)	C11—C12—H12B	109.8
O5ⁱⁱ—Zn1—O3	140.95 (10)	C11—C12—C20	109.3 (3)
O5ⁱⁱ—Zn1—C8	119.23 (10)	H12A—C12—H12B	108.3
C7—O1—C9	116.8 (2)	C20—C12—H12A	109.8
C8—O2—Zn1	97.5 (2)	C20—C12—H12B	109.8
C8—O3—Zn1	83.1 (2)	N1—C13—H13A	108.4
C6—O4—Zn1ⁱⁱⁱ	118.39 (19)	N1—C13—H13B	108.4
C6—O5—Zn1^iv	124.98 (18)	H13A—C13—H13B	107.5
C10—N1—C11	112.3 (2)	C14—C13—N1	115.4 (2)
C10—N1—C13	104.4 (2)	C14—C13—H13A	108.4
C10—N1—C16	112.4 (2)	C14—C13—H13B	108.4
C11—N1—C13	111.5 (2)	C13—C14—H14A	109.8
C16—N1—C11	105.2 (2)	C13—C14—H14B	109.8
C16—N1—C13	111.2 (2)	C13—C14—C15	109.4 (3)
C2—C1—C6	118.7 (2)	H14A—C14—H14B	108.2
C4—C1—C2	120.1 (2)	C15—C14—H14A	109.8
C4—C1—C6	121.2 (2)	C15—C14—H14B	109.8
C1—C2—H2	120.4	C14—C15—H15A	109.5
C7—C2—C1	119.3 (2)	C14—C15—H15B	109.5
C7—C2—H2	120.4	C14—C15—H15C	109.5
C4—C3—C8	121.3 (3)	H15A—C15—H15B	109.5
C5—C3—C4	120.1 (2)	H15A—C15—H15C	109.5
C5—C3—C8	118.5 (3)	H15B—C15—H15C	109.5
C1—C4—H4	120.0	N1—C16—H16A	108.1
C3—C4—C1	120.0 (3)	N1—C16—H16B	108.1
C3—C4—H4	120.0	H16A—C16—H16B	107.3
C3—C5—H5	120.2	C17—C16—N1	116.8 (2)
C3—C5—C7	119.6 (3)	C17—C16—H16A	108.1
C7—C5—H5	120.2	C17—C16—H16B	108.1
O4—C6—C1	117.1 (2)	C16—C17—H17A	109.7
O5—C6—O4	124.3 (3)	C16—C17—H17B	109.7
O5—C6—C1	118.6 (2)	C16—C17—C18	109.8 (3)
O1—C7—C2	123.8 (2)	H17A—C17—H17B	108.2
O1—C7—C5	115.3 (2)	C18—C17—H17A	109.7
C2—C7—C5	120.9 (3)	C18—C17—H17B	109.7
O2—C8—Zn1	53.74 (17)	C17—C18—H18A	109.5
O2—C8—C3	118.6 (3)	C17—C18—H18B	109.5
O3—C8—Zn1	68.14 (19)	C17—C18—H18C	109.5
O3—C8—O2	121.6 (3)	H18A—C18—H18B	109.5
O3—C8—C3	119.8 (3)	H18A—C18—H18C	109.5
C3—C8—Zn1	170.9 (3)	H18B—C18—H18C	109.5
O1—C9—H9A	109.8	C12—C20—H20A	109.5
O1—C9—H9B	109.8	C12—C20—H20B	109.5
O1—C9—C10	109.3 (2)	C12—C20—H20C	109.5
H9A—C9—H9B	108.3	H20A—C20—H20B	109.5
C10—C9—H9A	109.8	H20A—C20—H20C	109.5
C10—C9—H9B	109.8	H20B—C20—H20C	109.5
N1—C10—H10A	108.0

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

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