Tetra-kis[μ-4-(dimethyl-amino)benzoato-κO:O']bis-[(N,N-diethyl-nicotinamide-κN)zinc(II)].

The title mol-ecule, [Zn(2)(C(9)H(10)NO(2))(4)(C(10)H(14)N(2)O)(2)], is a centrosymmetric binuclear complex, with Zn atoms [Zn⋯Zn' = 2.8927 (4) Å] bridged by four carboxyl-ate groups from the dimethyl-amino-benzoate (DMAB) ligands. The four carboxyl O atoms around the Zn atom form a distorted square-planar arrangement; the distorted square-pyramidal coordination geometry is completed by the pyridine N atom of the N,N-diethyl-nicotinamide (DENA) ligand. The Zn atom is displaced by 0.3326 (2) Å from the plane of the four O atoms, with an average Zn-O distance of 2.0416 (12) Å. The dihedral angles between the carboxyl-ate groups and the adjacent benzene rings are 5.31 (8) and 11.00 (9)°, while the pyridine ring is oriented at dihedral angles of 66.26 (6) and 37.88 (7)° with respect to the benzene rings. Weak intra-molecular C-H⋯O and inter-molecular C-H⋯π inter-actions are present.

Related literature

For general background to niacin and the nicotinic acid derivative N,N-diethyl­nicotinamide (DENA), see: Bigoli et al. (1972 ▶); Krishnamachari (1974 ▶). For related structures, see: Hökelek et al. (1995 ▶, 2009a ▶,b ▶); Speier & Fulop (1989 ▶); Usubaliev et al. (1980 ▶).

Experimental

Crystal data

[Zn2(C9H10NO2)4(C10H14N2O)2]

M = 1143.96

Triclinic,

a = 9.2731 (6) Å

b = 13.2340 (8) Å

c = 13.4756 (8) Å

α = 112.348 (3)°

β = 109.236 (2)°

γ = 95.728 (2)°

V = 1395.33 (16) Å3

Z = 1

Mo Kα radiation

μ = 0.92 mm−1

T = 294 K

0.52 × 0.35 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.681, T max = 0.791

24970 measured reflections

6877 independent reflections

5749 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.090

S = 1.06

6877 reflections

349 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809047473/xu2669sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047473/xu2669Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Zn2(C9H10NO2)4(C10H14N2O)2]	Z = 1
Mr = 1143.96	F(000) = 600
Triclinic, P1	Dx = 1.361 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2731 (6) Å	Cell parameters from 9870 reflections
b = 13.2340 (8) Å	θ = 2.4–28.3°
c = 13.4756 (8) Å	µ = 0.92 mm−1
α = 112.348 (3)°	T = 294 K
β = 109.236 (2)°	Block, colorless
γ = 95.728 (2)°	0.52 × 0.35 × 0.25 mm
V = 1395.33 (16) Å3

Bruker Kappa APEXII CCD area-detector diffractometer	6877 independent reflections
Radiation source: fine-focus sealed tube	5749 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.681, Tmax = 0.791	k = −16→17
24970 measured reflections	l = −17→17

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0476P)2 + 0.2013P] where P = (Fo2 + 2Fc2)/3
6877 reflections	(Δ/σ)max = 0.001
349 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

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.

	x	y	z	Uiso*/Ueq
Zn1	0.647429 (19)	0.587023 (15)	0.565621 (14)	0.03318 (7)
N1	0.0447 (2)	0.97057 (18)	0.3697 (2)	0.0740 (6)
N2	0.3784 (2)	0.63356 (17)	1.11287 (14)	0.0626 (5)
N3	0.88138 (15)	0.67128 (11)	0.64273 (11)	0.0336 (3)
N4	1.16916 (19)	0.90139 (14)	1.01779 (14)	0.0529 (4)
O1	0.52598 (14)	0.69380 (11)	0.52284 (11)	0.0495 (3)
O2	0.58984 (16)	0.62604 (11)	0.70601 (11)	0.0514 (3)
O3	1.2203 (3)	1.00113 (14)	0.92564 (15)	0.0984 (7)
O4	0.69851 (15)	0.44310 (11)	0.57910 (12)	0.0515 (3)
O5	0.63255 (15)	0.51278 (12)	0.39761 (10)	0.0542 (3)
C1	0.3792 (2)	0.65704 (15)	0.46130 (14)	0.0387 (4)
C2	0.29154 (19)	0.73827 (14)	0.43619 (14)	0.0375 (4)
C3	0.1306 (2)	0.70435 (16)	0.36591 (16)	0.0466 (4)
H3	0.0769	0.6287	0.3333	0.056*
C4	0.0491 (2)	0.77940 (18)	0.34350 (18)	0.0533 (5)
H4	−0.0584	0.7536	0.2961	0.064*
C5	0.1243 (2)	0.89438 (17)	0.39039 (18)	0.0499 (4)
C6	0.2864 (2)	0.92796 (17)	0.46138 (18)	0.0512 (5)
H6	0.3409	1.0035	0.4947	0.061*
C7	0.3659 (2)	0.85148 (16)	0.48263 (16)	0.0453 (4)
H7	0.4734	0.8767	0.5299	0.054*
C8	0.1256 (3)	1.0887 (2)	0.4196 (2)	0.0767 (7)
H8A	0.0508	1.1301	0.3992	0.115*
H8B	0.2045	1.0961	0.3895	0.115*
H8C	0.1752	1.1183	0.5032	0.115*
C9	−0.1234 (3)	0.9381 (2)	0.3032 (2)	0.0778 (7)
H9A	−0.1586	1.0036	0.3019	0.117*
H9B	−0.1759	0.9056	0.3388	0.117*
H9C	−0.1478	0.8836	0.2247	0.117*
C10	0.4677 (2)	0.56674 (16)	0.69715 (14)	0.0418 (4)
C11	0.43798 (19)	0.58899 (15)	0.80439 (14)	0.0398 (4)
C12	0.3197 (2)	0.51570 (17)	0.80381 (15)	0.0486 (4)
H12	0.2529	0.4548	0.7334	0.058*
C13	0.2979 (2)	0.53000 (18)	0.90376 (17)	0.0531 (5)
H13	0.2169	0.4791	0.8997	0.064*
C14	0.3962 (2)	0.62048 (17)	1.01199 (15)	0.0478 (4)
C15	0.5102 (2)	0.69743 (18)	1.01119 (15)	0.0530 (5)
H15	0.5735	0.7608	1.0805	0.064*
C16	0.5308 (2)	0.68143 (17)	0.91032 (15)	0.0474 (4)
H16	0.6087	0.7337	0.9131	0.057*
C17	0.4929 (3)	0.7180 (2)	1.22593 (18)	0.0795 (7)
H17A	0.4760	0.7042	1.2867	0.119*
H17B	0.4808	0.7918	1.2350	0.119*
H17C	0.5977	0.7140	1.2310	0.119*
C18	0.2607 (3)	0.5536 (2)	1.1128 (2)	0.0754 (7)
H18A	0.2701	0.5743	1.1916	0.113*
H18B	0.2763	0.4793	1.0808	0.113*
H18C	0.1572	0.5539	1.0661	0.113*
C19	0.94694 (19)	0.75356 (14)	0.75189 (14)	0.0369 (4)
H19	0.8823	0.7750	0.7921	0.044*
C20	1.1054 (2)	0.80823 (15)	0.80792 (15)	0.0427 (4)
C21	1.2004 (2)	0.77375 (18)	0.74711 (18)	0.0539 (5)
H21	1.3080	0.8089	0.7816	0.065*
C22	1.1348 (2)	0.68765 (18)	0.63601 (18)	0.0537 (5)
H22	1.1976	0.6621	0.5951	0.064*
C23	0.9753 (2)	0.63968 (15)	0.58606 (15)	0.0416 (4)
H23	0.9305	0.5829	0.5097	0.050*
C24	1.1705 (2)	0.91161 (17)	0.92357 (17)	0.0536 (5)
C25	1.2270 (3)	1.0051 (2)	1.1274 (2)	0.0837 (8)
H25A	1.1758	0.9954	1.1766	0.100*
H25B	1.1973	1.0667	1.1101	0.100*
C26	1.4002 (4)	1.0362 (3)	1.1927 (3)	0.1230 (13)
H26A	1.4314	1.1060	1.2619	0.184*
H26B	1.4518	1.0449	1.1442	0.184*
H26C	1.4299	0.9777	1.2144	0.184*
C27	1.1366 (3)	0.79420 (19)	1.02381 (18)	0.0609 (5)
H27A	1.2212	0.7969	1.0912	0.073*
H27B	1.1368	0.7341	0.9545	0.073*
C28	0.9820 (4)	0.7661 (3)	1.0327 (3)	0.0990 (9)
H28A	0.9775	0.7036	1.0522	0.149*
H28B	0.8967	0.7463	0.9591	0.149*
H28C	0.9729	0.8306	1.0926	0.149*

	U11	U22	U33	U12	U13	U23
Zn1	0.02904 (10)	0.03429 (12)	0.03032 (10)	0.00543 (7)	0.01153 (7)	0.00929 (8)
N1	0.0647 (12)	0.0723 (13)	0.1079 (16)	0.0331 (10)	0.0319 (11)	0.0608 (12)
N2	0.0671 (11)	0.0820 (13)	0.0420 (9)	0.0147 (10)	0.0313 (8)	0.0238 (9)
N3	0.0325 (6)	0.0324 (7)	0.0342 (7)	0.0087 (5)	0.0142 (5)	0.0120 (6)
N4	0.0554 (10)	0.0441 (9)	0.0426 (8)	0.0082 (7)	0.0161 (7)	0.0065 (7)
O1	0.0403 (7)	0.0488 (8)	0.0577 (8)	0.0151 (6)	0.0144 (6)	0.0253 (6)
O2	0.0586 (8)	0.0561 (8)	0.0402 (7)	0.0107 (6)	0.0297 (6)	0.0145 (6)
O3	0.1420 (17)	0.0466 (10)	0.0616 (10)	−0.0197 (10)	0.0089 (10)	0.0166 (8)
O4	0.0514 (7)	0.0395 (7)	0.0664 (8)	0.0141 (6)	0.0237 (6)	0.0253 (6)
O5	0.0479 (7)	0.0726 (9)	0.0298 (6)	0.0141 (7)	0.0151 (5)	0.0108 (6)
C1	0.0444 (9)	0.0414 (10)	0.0387 (9)	0.0150 (7)	0.0233 (7)	0.0191 (8)
C2	0.0395 (8)	0.0417 (9)	0.0381 (8)	0.0118 (7)	0.0197 (7)	0.0202 (7)
C3	0.0426 (9)	0.0424 (10)	0.0513 (10)	0.0073 (8)	0.0159 (8)	0.0204 (8)
C4	0.0403 (9)	0.0593 (13)	0.0585 (12)	0.0129 (9)	0.0130 (8)	0.0296 (10)
C5	0.0522 (11)	0.0547 (12)	0.0596 (12)	0.0221 (9)	0.0271 (9)	0.0358 (10)
C6	0.0538 (11)	0.0411 (10)	0.0640 (12)	0.0108 (8)	0.0240 (9)	0.0284 (9)
C7	0.0398 (9)	0.0465 (10)	0.0510 (10)	0.0085 (8)	0.0173 (8)	0.0241 (9)
C8	0.0995 (19)	0.0644 (16)	0.0989 (19)	0.0435 (14)	0.0491 (16)	0.0549 (15)
C9	0.0682 (15)	0.104 (2)	0.0950 (19)	0.0481 (15)	0.0366 (14)	0.0672 (17)
C10	0.0423 (9)	0.0517 (11)	0.0345 (8)	0.0217 (8)	0.0190 (7)	0.0166 (8)
C11	0.0367 (8)	0.0509 (10)	0.0323 (8)	0.0161 (7)	0.0164 (7)	0.0153 (7)
C12	0.0471 (10)	0.0517 (11)	0.0359 (9)	0.0081 (8)	0.0150 (8)	0.0107 (8)
C13	0.0522 (11)	0.0602 (12)	0.0469 (10)	0.0069 (9)	0.0250 (9)	0.0210 (9)
C14	0.0488 (10)	0.0608 (12)	0.0391 (9)	0.0194 (9)	0.0243 (8)	0.0203 (9)
C15	0.0483 (10)	0.0634 (13)	0.0322 (9)	0.0059 (9)	0.0166 (8)	0.0075 (9)
C16	0.0410 (9)	0.0574 (12)	0.0374 (9)	0.0070 (8)	0.0191 (7)	0.0128 (8)
C17	0.0939 (18)	0.100 (2)	0.0390 (11)	0.0174 (15)	0.0317 (12)	0.0223 (12)
C18	0.0869 (17)	0.0942 (19)	0.0689 (15)	0.0242 (14)	0.0474 (14)	0.0456 (15)
C19	0.0358 (8)	0.0342 (9)	0.0345 (8)	0.0068 (7)	0.0140 (6)	0.0097 (7)
C20	0.0384 (9)	0.0404 (10)	0.0390 (9)	0.0039 (7)	0.0071 (7)	0.0160 (8)
C21	0.0300 (8)	0.0586 (12)	0.0637 (12)	0.0058 (8)	0.0136 (8)	0.0234 (10)
C22	0.0401 (9)	0.0651 (13)	0.0621 (12)	0.0180 (9)	0.0298 (9)	0.0249 (10)
C23	0.0402 (9)	0.0431 (10)	0.0391 (9)	0.0123 (7)	0.0197 (7)	0.0122 (8)
C24	0.0504 (11)	0.0419 (11)	0.0454 (10)	0.0019 (8)	0.0044 (8)	0.0113 (8)
C25	0.108 (2)	0.0578 (15)	0.0513 (13)	0.0038 (14)	0.0278 (13)	−0.0016 (11)
C26	0.110 (3)	0.107 (3)	0.0625 (17)	−0.029 (2)	−0.0102 (16)	0.0001 (16)
C27	0.0666 (13)	0.0592 (13)	0.0478 (11)	0.0142 (10)	0.0150 (10)	0.0215 (10)
C28	0.100 (2)	0.110 (2)	0.110 (2)	0.0161 (18)	0.0574 (19)	0.061 (2)

Zn1—Zn1i	2.8927 (4)	C11—C16	1.388 (2)
Zn1—O1	2.0265 (12)	C12—C13	1.373 (3)
Zn1—O2	2.0269 (12)	C12—H12	0.9300
Zn1—O4	2.0669 (12)	C13—H13	0.9300
Zn1—O5	2.0459 (12)	C14—N2	1.371 (2)
Zn1—N3	2.0446 (13)	C14—C13	1.404 (3)
O1—C1	1.263 (2)	C14—C15	1.399 (3)
O2—C10	1.255 (2)	C15—C16	1.374 (2)
O4—C1i	1.255 (2)	C15—H15	0.9300
O5—C10i	1.266 (2)	C16—H16	0.9300
N1—C9	1.438 (3)	C17—H17A	0.9600
N1—C8	1.447 (3)	C17—H17B	0.9600
N2—C18	1.443 (3)	C17—H17C	0.9600
N2—C17	1.449 (3)	C18—H18A	0.9600
N3—C19	1.334 (2)	C18—H18B	0.9600
N3—C23	1.336 (2)	C18—H18C	0.9600
N4—C25	1.463 (3)	C19—C20	1.377 (2)
N4—C27	1.459 (3)	C19—H19	0.9300
C1—O4i	1.255 (2)	C20—C21	1.388 (3)
C2—C1	1.484 (2)	C20—C24	1.503 (2)
C2—C3	1.392 (2)	C21—H21	0.9300
C2—C7	1.381 (2)	C22—C21	1.369 (3)
C3—C4	1.369 (3)	C22—H22	0.9300
C3—H3	0.9300	C23—C22	1.370 (2)
C4—C5	1.403 (3)	C23—H23	0.9300
C4—H4	0.9300	C24—O3	1.214 (3)
C5—N1	1.366 (2)	C24—N4	1.331 (3)
C6—C5	1.402 (3)	C25—C26	1.478 (4)
C6—H6	0.9300	C25—H25A	0.9700
C7—C6	1.371 (3)	C25—H25B	0.9700
C7—H7	0.9300	C26—H26A	0.9600
C8—H8A	0.9600	C26—H26B	0.9600
C8—H8B	0.9600	C26—H26C	0.9600
C8—H8C	0.9600	C27—C28	1.500 (3)
C9—H9A	0.9600	C27—H27A	0.9700
C9—H9B	0.9600	C27—H27B	0.9700
C9—H9C	0.9600	C28—H28A	0.9600
C10—O5i	1.266 (2)	C28—H28B	0.9600
C11—C10	1.485 (2)	C28—H28C	0.9600
C11—C12	1.386 (3)
O1—Zn1—O2	89.01 (6)	C13—C12—H12	118.9
O1—Zn1—O4	161.34 (5)	C12—C13—C14	120.84 (18)
O1—Zn1—O5	88.39 (6)	C12—C13—H13	119.6
O1—Zn1—N3	106.31 (5)	C14—C13—H13	119.6
O2—Zn1—O4	89.28 (6)	N2—C14—C13	121.29 (18)
O2—Zn1—O5	161.09 (6)	N2—C14—C15	121.92 (18)
O2—Zn1—N3	101.76 (5)	C15—C14—C13	116.77 (16)
O5—Zn1—O4	87.23 (6)	C16—C15—C14	121.46 (18)
N3—Zn1—O4	92.23 (5)	C16—C15—H15	119.3
N3—Zn1—O5	96.95 (5)	C14—C15—H15	119.3
C1—O1—Zn1	118.82 (11)	C11—C16—H16	119.2
C10—O2—Zn1	119.77 (11)	C15—C16—C11	121.52 (18)
C1i—O4—Zn1	135.03 (12)	C15—C16—H16	119.2
C10i—O5—Zn1	134.43 (12)	N2—C17—H17A	109.5
C5—N1—C8	120.9 (2)	N2—C17—H17B	109.5
C5—N1—C9	121.6 (2)	N2—C17—H17C	109.5
C9—N1—C8	117.41 (19)	H17A—C17—H17B	109.5
C14—N2—C17	120.85 (19)	H17A—C17—H17C	109.5
C14—N2—C18	121.51 (19)	H17B—C17—H17C	109.5
C18—N2—C17	116.96 (18)	N2—C18—H18A	109.5
C19—N3—Zn1	121.99 (11)	N2—C18—H18B	109.5
C19—N3—C23	118.04 (14)	N2—C18—H18C	109.5
C23—N3—Zn1	119.85 (11)	H18A—C18—H18B	109.5
C24—N4—C25	117.08 (19)	H18A—C18—H18C	109.5
C24—N4—C27	124.81 (17)	H18B—C18—H18C	109.5
C27—N4—C25	117.48 (18)	N3—C19—C20	123.28 (15)
O1—C1—C2	117.78 (15)	N3—C19—H19	118.4
O4i—C1—O1	124.74 (16)	C20—C19—H19	118.4
O4i—C1—C2	117.47 (15)	C19—C20—C21	117.52 (16)
C3—C2—C1	121.68 (16)	C19—C20—C24	121.55 (16)
C7—C2—C1	121.40 (15)	C21—C20—C24	120.41 (16)
C7—C2—C3	116.92 (16)	C20—C21—H21	120.2
C2—C3—H3	119.1	C22—C21—C20	119.63 (16)
C4—C3—C2	121.76 (17)	C22—C21—H21	120.2
C4—C3—H3	119.1	C21—C22—C23	118.90 (17)
C3—C4—C5	121.46 (18)	C21—C22—H22	120.6
C3—C4—H4	119.3	C23—C22—H22	120.6
C5—C4—H4	119.3	N3—C23—C22	122.60 (16)
N1—C5—C4	122.23 (19)	N3—C23—H23	118.7
N1—C5—C6	121.32 (19)	C22—C23—H23	118.7
C6—C5—C4	116.45 (17)	O3—C24—N4	123.26 (19)
C5—C6—H6	119.4	O3—C24—C20	117.73 (19)
C7—C6—C5	121.22 (18)	N4—C24—C20	119.00 (18)
C7—C6—H6	119.4	N4—C25—C26	113.3 (2)
C2—C7—H7	118.9	N4—C25—H25A	108.9
C6—C7—C2	122.19 (17)	N4—C25—H25B	108.9
C6—C7—H7	118.9	C26—C25—H25A	108.9
N1—C8—H8A	109.5	C26—C25—H25B	108.9
N1—C8—H8B	109.5	H25A—C25—H25B	107.7
N1—C8—H8C	109.5	C25—C26—H26A	109.5
H8A—C8—H8B	109.5	C25—C26—H26B	109.5
H8A—C8—H8C	109.5	C25—C26—H26C	109.5
H8B—C8—H8C	109.5	H26A—C26—H26B	109.5
N1—C9—H9A	109.5	H26A—C26—H26C	109.5
N1—C9—H9B	109.5	H26B—C26—H26C	109.5
N1—C9—H9C	109.5	N4—C27—C28	113.8 (2)
H9A—C9—H9B	109.5	N4—C27—H27A	108.8
H9A—C9—H9C	109.5	N4—C27—H27B	108.8
H9B—C9—H9C	109.5	C28—C27—H27A	108.8
O2—C10—O5i	124.39 (16)	C28—C27—H27B	108.8
O2—C10—C11	118.63 (15)	H27A—C27—H27B	107.7
O5i—C10—C11	116.98 (16)	C27—C28—H28A	109.5
C12—C11—C10	121.20 (16)	C27—C28—H28B	109.5
C12—C11—C16	117.10 (16)	C27—C28—H28C	109.5
C16—C11—C10	121.66 (16)	H28A—C28—H28B	109.5
C11—C12—H12	118.9	H28A—C28—H28C	109.5
C13—C12—C11	122.17 (17)	H28B—C28—H28C	109.5
O2—Zn1—O1—C1	−86.30 (13)	C3—C2—C7—C6	0.1 (3)
O4—Zn1—O1—C1	−1.5 (2)	C2—C3—C4—C5	0.0 (3)
O5—Zn1—O1—C1	74.97 (13)	C3—C4—C5—N1	−179.4 (2)
N3—Zn1—O1—C1	171.73 (12)	C3—C4—C5—C6	−0.2 (3)
O1—Zn1—O2—C10	92.13 (14)	C4—C5—N1—C8	179.9 (2)
O4—Zn1—O2—C10	−69.29 (14)	C4—C5—N1—C9	3.2 (3)
O5—Zn1—O2—C10	10.0 (3)	C6—C5—N1—C8	0.7 (3)
N3—Zn1—O2—C10	−161.42 (14)	C6—C5—N1—C9	−176.0 (2)
O1—Zn1—O4—C1i	4.3 (3)	C7—C6—C5—N1	179.6 (2)
O2—Zn1—O4—C1i	89.10 (17)	C7—C6—C5—C4	0.3 (3)
O5—Zn1—O4—C1i	−72.31 (17)	C2—C7—C6—C5	−0.2 (3)
N3—Zn1—O4—C1i	−169.16 (17)	C12—C11—C10—O2	−169.73 (18)
O1—Zn1—O5—C10i	−88.02 (18)	C12—C11—C10—O5i	9.4 (3)
O2—Zn1—O5—C10i	−5.8 (3)	C16—C11—C10—O2	7.8 (3)
O4—Zn1—O5—C10i	73.84 (18)	C16—C11—C10—O5i	−173.06 (17)
N3—Zn1—O5—C10i	165.75 (17)	C10—C11—C12—C13	175.00 (17)
O1—Zn1—N3—C19	75.41 (13)	C16—C11—C12—C13	−2.7 (3)
O1—Zn1—N3—C23	−108.69 (13)	C10—C11—C16—C15	−175.32 (17)
O2—Zn1—N3—C19	−17.02 (14)	C12—C11—C16—C15	2.3 (3)
O2—Zn1—N3—C23	158.88 (13)	C11—C12—C13—C14	−0.2 (3)
O4—Zn1—N3—C19	−106.75 (13)	C13—C14—N2—C17	171.8 (2)
O4—Zn1—N3—C23	69.15 (13)	C13—C14—N2—C18	1.6 (3)
O5—Zn1—N3—C19	165.77 (13)	C15—C14—N2—C17	−9.6 (3)
O5—Zn1—N3—C23	−18.33 (14)	C15—C14—N2—C18	−179.8 (2)
Zn1—O1—C1—O4i	−2.1 (2)	N2—C14—C13—C12	−178.00 (19)
Zn1—O1—C1—C2	176.98 (10)	C15—C14—C13—C12	3.3 (3)
Zn1—O2—C10—O5i	−5.9 (3)	N2—C14—C15—C16	177.68 (19)
Zn1—O2—C10—C11	173.11 (11)	C13—C14—C15—C16	−3.7 (3)
Zn1—N3—C19—C20	176.95 (13)	C14—C15—C16—C11	0.9 (3)
Zn1—N3—C23—C22	−175.48 (15)	N3—C19—C20—C21	−1.0 (3)
C19—N3—C23—C22	0.6 (3)	N3—C19—C20—C24	170.73 (17)
C23—N3—C19—C20	1.0 (2)	C19—C20—C21—C22	−0.5 (3)
C24—N4—C25—C26	−86.0 (3)	C24—C20—C21—C22	−172.34 (19)
C27—N4—C25—C26	85.3 (3)	C19—C20—C24—O3	−111.7 (2)
C24—N4—C27—C28	−110.6 (2)	C19—C20—C24—N4	67.5 (2)
C25—N4—C27—C28	78.8 (3)	C21—C20—C24—O3	59.8 (3)
C3—C2—C1—O1	177.84 (16)	C21—C20—C24—N4	−121.0 (2)
C3—C2—C1—O4i	−3.0 (2)	C23—C22—C21—C20	2.0 (3)
C7—C2—C1—O1	−2.8 (2)	N3—C23—C22—C21	−2.0 (3)
C7—C2—C1—O4i	176.30 (16)	O3—C24—N4—C25	1.9 (3)
C1—C2—C3—C4	179.40 (17)	O3—C24—N4—C27	−168.7 (2)
C7—C2—C3—C4	0.1 (3)	C20—C24—N4—C25	−177.29 (19)
C1—C2—C7—C6	−179.29 (17)	C20—C24—N4—C27	12.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O5	0.93	2.54	3.122 (2)	121
C8—H8A···Cg3ii	0.96	2.77	3.629 (3)	150

Table 1

Selected bond lengths (Å)

Zn1—O1	2.0265 (12)
Zn1—O2	2.0269 (12)
Zn1—O4	2.0669 (12)
Zn1—O5	2.0459 (12)
Zn1—N3	2.0446 (13)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯O5	0.93	2.54	3.122 (2)	121
C8—H8A⋯Cg3i	0.96	2.77	3.629 (3)	150

Symmetry code: (i) . Cg3 is the centroid of the N3/C19–C23 ring.