Bis(4-amino-benzoato)-κO,O';κO-(2,2'-bipyridine-κN,N')zinc.

In the title complex, [Zn(C(7)H(6)NO(2))(2)(C(10)H(8)N(2))], the Zn(II) cation is coordinated by two amino-benzoate anions and one 2,2'-bipyridine ligand in a distorted trigonal-bipyramidal geometry. The carboxyl-ate group of one aminobenzoate anion coordinates to the Zn(II) cation in a monodentate manner, whereas the carboxyl-ate group of the other amino-benzoate anion chelates the Zn cation with different Zn-O bond lengths. Inter-molecular N-H⋯N and N-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For applications of Zn complexes, see: Chohan & Naseer (2007 ▶); Huang et al. (2006 ▶); Ispir et al. (2006 ▶); Lo et al. (2007 ▶); Maria et al. (1996 ▶). For a related structure, see: Wang et al. (2005 ▶).

Experimental

Crystal data

[Zn(C7H6NO2)2(C10H8N2)]

M = 493.81

Triclinic,

a = 7.9499 (14) Å

b = 10.7281 (19) Å

c = 13.905 (2) Å

α = 80.499 (2)°

β = 80.921 (2)°

γ = 70.538 (2)°

V = 1096.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.16 mm−1

T = 295 K

0.42 × 0.23 × 0.08 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.643, T max = 0.914

8223 measured reflections

4058 independent reflections

3419 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.090

S = 1.07

4058 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811039389/xu5334sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039389/xu5334Isup2.hkl

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

[Zn(C7H6NO2)2(C10H8N2)]	Z = 2
Mr = 493.81	F(000) = 508
Triclinic, P1	Dx = 1.496 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9499 (14) Å	Cell parameters from 2868 reflections
b = 10.7281 (19) Å	θ = 2.4–24.9°
c = 13.905 (2) Å	µ = 1.16 mm−1
α = 80.499 (2)°	T = 295 K
β = 80.921 (2)°	Block, colourless
γ = 70.538 (2)°	0.42 × 0.23 × 0.08 mm
V = 1096.1 (3) Å3

Bruker SMART 1000 CCD area-detector diffractometer	4058 independent reflections
Radiation source: fine-focus sealed tube	3419 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.643, Tmax = 0.914	k = −12→12
8223 measured reflections	l = −16→16

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0411P)2 + 0.2825P] where P = (Fo2 + 2Fc2)/3
4058 reflections	(Δ/σ)max < 0.001
298 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.31 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	0.14918 (4)	0.12380 (3)	0.19516 (2)	0.04021 (12)
O1	−0.1044 (2)	0.2151 (2)	0.21855 (14)	0.0528 (5)
O2	−0.0311 (3)	0.3661 (2)	0.27669 (18)	0.0732 (7)
O3	0.3785 (3)	0.10054 (19)	0.24420 (15)	0.0558 (5)
O4	0.2405 (3)	−0.0296 (2)	0.33755 (15)	0.0663 (6)
N1	−0.8907 (3)	0.5767 (3)	0.3483 (2)	0.0678 (7)
H1D	−0.9291	0.6259	0.3971	0.102*
H1E	−0.9611	0.5323	0.3389	0.102*
N2	1.0034 (4)	−0.2214 (3)	0.5101 (2)	0.0788 (9)
H2D	1.0548	−0.1604	0.5101	0.118*
H2E	0.9810	−0.2610	0.5693	0.118*
N3	0.2165 (3)	0.1976 (2)	0.04781 (16)	0.0502 (6)
N4	0.1805 (3)	−0.0382 (2)	0.12124 (15)	0.0419 (5)
C1	−0.3406 (3)	0.3914 (2)	0.28122 (17)	0.0362 (5)
C2	−0.4024 (4)	0.4919 (3)	0.3417 (2)	0.0488 (7)
H2	−0.3201	0.5185	0.3670	0.059*
C3	−0.5831 (4)	0.5529 (3)	0.3648 (2)	0.0537 (7)
H3	−0.6211	0.6196	0.4057	0.064*
C4	−0.7100 (3)	0.5157 (3)	0.3275 (2)	0.0444 (6)
C5	−0.6484 (3)	0.4166 (2)	0.26597 (19)	0.0417 (6)
H5	−0.7303	0.3914	0.2391	0.050*
C6	−0.4677 (3)	0.3554 (2)	0.24420 (18)	0.0375 (5)
H6	−0.4297	0.2882	0.2036	0.045*
C7	−0.1451 (3)	0.3227 (3)	0.25832 (18)	0.0423 (6)
C8	0.5359 (3)	−0.0506 (2)	0.36920 (17)	0.0368 (5)
C9	0.5508 (4)	−0.1572 (3)	0.44177 (19)	0.0479 (7)
H9	0.4560	−0.1919	0.4589	0.058*
C10	0.7028 (4)	−0.2133 (3)	0.4894 (2)	0.0560 (8)
H10	0.7105	−0.2861	0.5372	0.067*
C11	0.8444 (4)	−0.1614 (3)	0.4663 (2)	0.0495 (7)
C12	0.8290 (3)	−0.0533 (3)	0.3952 (2)	0.0474 (6)
H12	0.9222	−0.0167	0.3796	0.057*
C13	0.6791 (3)	0.0007 (3)	0.34731 (18)	0.0416 (6)
H13	0.6723	0.0730	0.2992	0.050*
C14	0.3746 (3)	0.0096 (3)	0.3162 (2)	0.0456 (6)
C15	0.2298 (5)	0.3190 (3)	0.0162 (3)	0.0771 (10)
H15	0.2011	0.3809	0.0607	0.093*
C16	0.2848 (7)	0.3549 (4)	−0.0801 (3)	0.1001 (14)
H16	0.2920	0.4402	−0.1006	0.120*
C17	0.3286 (6)	0.2642 (5)	−0.1448 (3)	0.0988 (14)
H17	0.3678	0.2865	−0.2100	0.119*
C18	0.3146 (5)	0.1395 (4)	−0.1135 (2)	0.0714 (9)
H18	0.3437	0.0765	−0.1571	0.086*
C19	0.2563 (3)	0.1089 (3)	−0.01574 (19)	0.0479 (7)
C20	0.2330 (3)	−0.0219 (3)	0.02410 (19)	0.0461 (6)
C21	0.2580 (5)	−0.1217 (3)	−0.0330 (2)	0.0702 (9)
H21	0.2929	−0.1097	−0.1000	0.084*
C22	0.2307 (6)	−0.2389 (4)	0.0103 (3)	0.0783 (10)
H22	0.2470	−0.3069	−0.0274	0.094*
C23	0.1794 (5)	−0.2557 (3)	0.1088 (2)	0.0673 (9)
H23	0.1607	−0.3348	0.1390	0.081*
C24	0.1561 (4)	−0.1535 (3)	0.1622 (2)	0.0534 (7)
H24	0.1221	−0.1648	0.2293	0.064*

	U11	U22	U33	U12	U13	U23
Zn1	0.03267 (17)	0.04633 (19)	0.03920 (18)	−0.00652 (13)	−0.00538 (12)	−0.00961 (13)
O1	0.0335 (9)	0.0589 (12)	0.0619 (12)	−0.0044 (9)	−0.0064 (8)	−0.0168 (10)
O2	0.0385 (11)	0.0841 (16)	0.1075 (19)	−0.0255 (11)	−0.0096 (11)	−0.0263 (14)
O3	0.0480 (11)	0.0515 (12)	0.0688 (13)	−0.0078 (9)	−0.0261 (10)	−0.0074 (10)
O4	0.0385 (11)	0.1067 (18)	0.0642 (13)	−0.0291 (11)	−0.0019 (9)	−0.0299 (12)
N1	0.0407 (13)	0.0650 (17)	0.092 (2)	−0.0066 (12)	0.0100 (13)	−0.0317 (15)
N2	0.0660 (18)	0.0786 (19)	0.0765 (19)	0.0202 (15)	−0.0384 (15)	−0.0286 (15)
N3	0.0525 (14)	0.0509 (14)	0.0436 (13)	−0.0125 (11)	−0.0062 (11)	−0.0024 (11)
N4	0.0386 (11)	0.0477 (13)	0.0367 (12)	−0.0080 (10)	−0.0058 (9)	−0.0080 (10)
C1	0.0333 (12)	0.0379 (13)	0.0360 (13)	−0.0109 (10)	−0.0050 (10)	−0.0006 (11)
C2	0.0466 (16)	0.0530 (17)	0.0544 (17)	−0.0212 (13)	−0.0054 (13)	−0.0165 (13)
C3	0.0538 (17)	0.0496 (17)	0.0607 (18)	−0.0152 (14)	0.0040 (14)	−0.0272 (14)
C4	0.0370 (13)	0.0389 (14)	0.0521 (16)	−0.0087 (11)	0.0046 (12)	−0.0069 (12)
C5	0.0346 (13)	0.0412 (14)	0.0519 (15)	−0.0135 (11)	−0.0053 (11)	−0.0092 (12)
C6	0.0361 (13)	0.0355 (13)	0.0392 (13)	−0.0078 (10)	−0.0030 (10)	−0.0089 (11)
C7	0.0371 (14)	0.0484 (16)	0.0369 (14)	−0.0096 (12)	−0.0068 (11)	0.0012 (12)
C8	0.0330 (12)	0.0403 (14)	0.0373 (13)	−0.0090 (10)	−0.0007 (10)	−0.0133 (11)
C9	0.0513 (16)	0.0508 (16)	0.0463 (15)	−0.0246 (13)	0.0056 (13)	−0.0115 (13)
C10	0.074 (2)	0.0433 (16)	0.0413 (15)	−0.0070 (15)	−0.0095 (14)	0.0011 (12)
C11	0.0436 (15)	0.0522 (16)	0.0433 (15)	0.0072 (13)	−0.0117 (12)	−0.0200 (13)
C12	0.0339 (13)	0.0607 (18)	0.0493 (16)	−0.0137 (13)	−0.0017 (12)	−0.0166 (14)
C13	0.0380 (14)	0.0432 (14)	0.0421 (14)	−0.0116 (11)	−0.0056 (11)	−0.0025 (11)
C14	0.0349 (14)	0.0535 (17)	0.0504 (16)	−0.0071 (12)	−0.0044 (12)	−0.0270 (14)
C15	0.111 (3)	0.059 (2)	0.064 (2)	−0.034 (2)	−0.013 (2)	0.0027 (17)
C16	0.150 (4)	0.081 (3)	0.072 (3)	−0.056 (3)	−0.009 (3)	0.021 (2)
C17	0.128 (4)	0.107 (3)	0.055 (2)	−0.048 (3)	0.008 (2)	0.013 (2)
C18	0.083 (2)	0.077 (2)	0.0436 (17)	−0.0196 (19)	0.0055 (16)	−0.0039 (16)
C19	0.0380 (14)	0.0542 (17)	0.0414 (15)	−0.0035 (12)	−0.0025 (11)	−0.0029 (13)
C20	0.0405 (14)	0.0507 (16)	0.0413 (15)	−0.0034 (12)	−0.0083 (11)	−0.0093 (12)
C21	0.095 (3)	0.065 (2)	0.0431 (17)	−0.0107 (19)	−0.0063 (17)	−0.0166 (15)
C22	0.114 (3)	0.058 (2)	0.063 (2)	−0.017 (2)	−0.016 (2)	−0.0232 (17)
C23	0.090 (2)	0.0486 (18)	0.066 (2)	−0.0206 (17)	−0.0171 (18)	−0.0092 (16)
C24	0.0610 (18)	0.0525 (17)	0.0464 (16)	−0.0170 (14)	−0.0079 (13)	−0.0054 (13)

Zn1—O1	1.9269 (18)	C6—H6	0.9300
Zn1—O3	1.9704 (18)	C8—C9	1.381 (4)
Zn1—O4	2.395 (2)	C8—C13	1.394 (3)
Zn1—N3	2.124 (2)	C8—C14	1.481 (4)
Zn1—N4	2.088 (2)	C9—C10	1.377 (4)
Zn1—C14	2.521 (3)	C9—H9	0.9300
O1—C7	1.284 (3)	C10—C11	1.387 (4)
O2—C7	1.223 (3)	C10—H10	0.9300
O3—C14	1.282 (3)	C11—C12	1.380 (4)
O4—C14	1.249 (3)	C12—C13	1.364 (3)
N1—C4	1.372 (3)	C12—H12	0.9300
N1—H1D	0.8818	C13—H13	0.9300
N1—H1E	0.8820	C15—C16	1.375 (5)
N2—C11	1.397 (3)	C15—H15	0.9300
N2—H2D	0.8798	C16—C17	1.358 (6)
N2—H2E	0.8825	C16—H16	0.9300
N3—C19	1.332 (4)	C17—C18	1.372 (5)
N3—C15	1.338 (4)	C17—H17	0.9300
N4—C24	1.335 (3)	C18—C19	1.388 (4)
N4—C20	1.350 (3)	C18—H18	0.9300
C1—C2	1.388 (4)	C19—C20	1.481 (4)
C1—C6	1.388 (3)	C20—C21	1.381 (4)
C1—C7	1.490 (3)	C21—C22	1.371 (5)
C2—C3	1.375 (4)	C21—H21	0.9300
C2—H2	0.9300	C22—C23	1.367 (5)
C3—C4	1.396 (4)	C22—H22	0.9300
C3—H3	0.9300	C23—C24	1.371 (4)
C4—C5	1.386 (4)	C23—H23	0.9300
C5—C6	1.373 (3)	C24—H24	0.9300
C5—H5	0.9300
O1—Zn1—O3	141.27 (9)	C13—C8—C14	120.3 (2)
O1—Zn1—N4	107.51 (8)	C10—C9—C8	121.5 (3)
O3—Zn1—N4	108.58 (8)	C10—C9—H9	119.2
O1—Zn1—N3	103.23 (9)	C8—C9—H9	119.2
O3—Zn1—N3	97.43 (9)	C9—C10—C11	120.2 (3)
N4—Zn1—N3	78.22 (9)	C9—C10—H10	119.9
O1—Zn1—O4	108.31 (8)	C11—C10—H10	119.9
O3—Zn1—O4	59.37 (8)	C12—C11—C10	118.6 (2)
N4—Zn1—O4	88.61 (8)	C12—C11—N2	120.4 (3)
N3—Zn1—O4	148.23 (8)	C10—C11—N2	120.9 (3)
O1—Zn1—C14	129.59 (8)	C13—C12—C11	121.0 (3)
O3—Zn1—C14	30.11 (8)	C13—C12—H12	119.5
N4—Zn1—C14	98.66 (8)	C11—C12—H12	119.5
N3—Zn1—C14	124.19 (9)	C12—C13—C8	121.2 (2)
O4—Zn1—C14	29.29 (8)	C12—C13—H13	119.4
C7—O1—Zn1	114.85 (16)	C8—C13—H13	119.4
C14—O3—Zn1	99.43 (16)	O4—C14—O3	120.2 (3)
C14—O4—Zn1	80.92 (18)	O4—C14—C8	121.8 (3)
C4—N1—H1D	119.3	O3—C14—C8	118.0 (2)
C4—N1—H1E	115.8	O4—C14—Zn1	69.79 (16)
H1D—N1—H1E	115.8	O3—C14—Zn1	50.46 (12)
C11—N2—H2D	108.4	C8—C14—Zn1	167.2 (2)
C11—N2—H2E	110.2	N3—C15—C16	121.9 (4)
H2D—N2—H2E	113.1	N3—C15—H15	119.1
C19—N3—C15	119.3 (3)	C16—C15—H15	119.1
C19—N3—Zn1	114.43 (18)	C17—C16—C15	119.1 (4)
C15—N3—Zn1	126.2 (2)	C17—C16—H16	120.5
C24—N4—C20	119.2 (2)	C15—C16—H16	120.5
C24—N4—Zn1	125.67 (18)	C16—C17—C18	119.6 (3)
C20—N4—Zn1	115.14 (18)	C16—C17—H17	120.2
C2—C1—C6	117.6 (2)	C18—C17—H17	120.2
C2—C1—C7	121.3 (2)	C17—C18—C19	118.9 (3)
C6—C1—C7	121.1 (2)	C17—C18—H18	120.5
C3—C2—C1	121.3 (2)	C19—C18—H18	120.5
C3—C2—H2	119.4	N3—C19—C18	121.2 (3)
C1—C2—H2	119.4	N3—C19—C20	116.1 (2)
C2—C3—C4	120.8 (2)	C18—C19—C20	122.7 (3)
C2—C3—H3	119.6	N4—C20—C21	120.7 (3)
C4—C3—H3	119.6	N4—C20—C19	115.9 (2)
N1—C4—C5	120.3 (3)	C21—C20—C19	123.4 (3)
N1—C4—C3	121.7 (3)	C22—C21—C20	119.3 (3)
C5—C4—C3	118.0 (2)	C22—C21—H21	120.4
C6—C5—C4	120.8 (2)	C20—C21—H21	120.4
C6—C5—H5	119.6	C23—C22—C21	119.9 (3)
C4—C5—H5	119.6	C23—C22—H22	120.0
C5—C6—C1	121.6 (2)	C21—C22—H22	120.0
C5—C6—H6	119.2	C22—C23—C24	118.5 (3)
C1—C6—H6	119.2	C22—C23—H23	120.7
O2—C7—O1	122.4 (2)	C24—C23—H23	120.7
O2—C7—C1	122.0 (3)	N4—C24—C23	122.4 (3)
O1—C7—C1	115.6 (2)	N4—C24—H24	118.8
C9—C8—C13	117.5 (2)	C23—C24—H24	118.8
C9—C8—C14	122.2 (2)
O3—Zn1—O1—C7	26.2 (3)	C10—C11—C12—C13	−0.9 (4)
N4—Zn1—O1—C7	−175.82 (17)	N2—C11—C12—C13	175.6 (2)
N3—Zn1—O1—C7	−94.20 (19)	C11—C12—C13—C8	0.6 (4)
O4—Zn1—O1—C7	89.73 (19)	C9—C8—C13—C12	0.6 (4)
C14—Zn1—O1—C7	66.4 (2)	C14—C8—C13—C12	−179.9 (2)
O1—Zn1—O3—C14	83.1 (2)	Zn1—O4—C14—O3	3.2 (2)
N4—Zn1—O3—C14	−74.76 (17)	Zn1—O4—C14—C8	−173.9 (2)
N3—Zn1—O3—C14	−154.77 (16)	Zn1—O3—C14—O4	−3.9 (3)
O4—Zn1—O3—C14	2.02 (14)	Zn1—O3—C14—C8	173.36 (18)
O1—Zn1—O4—C14	−141.45 (15)	C9—C8—C14—O4	3.2 (4)
O3—Zn1—O4—C14	−2.07 (15)	C13—C8—C14—O4	−176.3 (2)
N4—Zn1—O4—C14	110.56 (16)	C9—C8—C14—O3	−174.0 (2)
N3—Zn1—O4—C14	45.8 (2)	C13—C8—C14—O3	6.5 (3)
O1—Zn1—N3—C19	−109.74 (19)	C9—C8—C14—Zn1	−150.2 (7)
O3—Zn1—N3—C19	103.24 (19)	C13—C8—C14—Zn1	30.3 (9)
N4—Zn1—N3—C19	−4.28 (19)	O1—Zn1—C14—O4	50.15 (19)
O4—Zn1—N3—C19	63.2 (3)	O3—Zn1—C14—O4	176.4 (3)
C14—Zn1—N3—C19	88.3 (2)	N4—Zn1—C14—O4	−71.23 (16)
O1—Zn1—N3—C15	73.6 (3)	N3—Zn1—C14—O4	−152.83 (15)
O3—Zn1—N3—C15	−73.4 (3)	O1—Zn1—C14—O3	−126.29 (17)
N4—Zn1—N3—C15	179.1 (3)	N4—Zn1—C14—O3	112.32 (16)
O4—Zn1—N3—C15	−113.5 (3)	N3—Zn1—C14—O3	30.7 (2)
C14—Zn1—N3—C15	−88.4 (3)	O4—Zn1—C14—O3	−176.4 (3)
O1—Zn1—N4—C24	−77.9 (2)	O1—Zn1—C14—C8	−153.8 (8)
O3—Zn1—N4—C24	87.8 (2)	O3—Zn1—C14—C8	−27.5 (8)
N3—Zn1—N4—C24	−178.2 (2)	N4—Zn1—C14—C8	84.8 (8)
O4—Zn1—N4—C24	30.9 (2)	N3—Zn1—C14—C8	3.2 (9)
C14—Zn1—N4—C24	58.5 (2)	O4—Zn1—C14—C8	156.1 (9)
O1—Zn1—N4—C20	103.27 (18)	C19—N3—C15—C16	−0.5 (5)
O3—Zn1—N4—C20	−91.02 (18)	Zn1—N3—C15—C16	176.0 (3)
N3—Zn1—N4—C20	2.95 (17)	N3—C15—C16—C17	−0.7 (7)
O4—Zn1—N4—C20	−147.95 (18)	C15—C16—C17—C18	1.0 (7)
C14—Zn1—N4—C20	−120.34 (18)	C16—C17—C18—C19	−0.2 (6)
C6—C1—C2—C3	0.6 (4)	C15—N3—C19—C18	1.3 (4)
C7—C1—C2—C3	−178.3 (2)	Zn1—N3—C19—C18	−175.6 (2)
C1—C2—C3—C4	−0.3 (4)	C15—N3—C19—C20	−178.2 (3)
C2—C3—C4—N1	−178.9 (3)	Zn1—N3—C19—C20	4.9 (3)
C2—C3—C4—C5	−0.6 (4)	C17—C18—C19—N3	−0.9 (5)
N1—C4—C5—C6	179.6 (2)	C17—C18—C19—C20	178.5 (3)
C3—C4—C5—C6	1.3 (4)	C24—N4—C20—C21	1.3 (4)
C4—C5—C6—C1	−1.1 (4)	Zn1—N4—C20—C21	−179.8 (2)
C2—C1—C6—C5	0.1 (4)	C24—N4—C20—C19	179.7 (2)
C7—C1—C6—C5	179.0 (2)	Zn1—N4—C20—C19	−1.4 (3)
Zn1—O1—C7—O2	2.4 (3)	N3—C19—C20—N4	−2.4 (3)
Zn1—O1—C7—C1	−177.28 (15)	C18—C19—C20—N4	178.1 (3)
C2—C1—C7—O2	−13.1 (4)	N3—C19—C20—C21	176.0 (3)
C6—C1—C7—O2	168.1 (3)	C18—C19—C20—C21	−3.5 (4)
C2—C1—C7—O1	166.6 (2)	N4—C20—C21—C22	−0.7 (5)
C6—C1—C7—O1	−12.2 (3)	C19—C20—C21—C22	−179.0 (3)
C13—C8—C9—C10	−1.5 (4)	C20—C21—C22—C23	0.0 (6)
C14—C8—C9—C10	179.0 (2)	C21—C22—C23—C24	0.1 (6)
C8—C9—C10—C11	1.2 (4)	C20—N4—C24—C23	−1.2 (4)
C9—C10—C11—C12	0.0 (4)	Zn1—N4—C24—C23	−180.0 (2)
C9—C10—C11—N2	−176.5 (2)	C22—C23—C24—N4	0.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···N2i	0.88	2.33	3.202 (4)	169.
N1—H1E···O2ii	0.88	2.36	3.181 (4)	155.
N2—H2E···O2iii	0.88	2.28	3.116 (4)	159.

Table 1

Selected bond lengths (Å)

Zn1—O1	1.9269 (18)
Zn1—O3	1.9704 (18)
Zn1—O4	2.395 (2)
Zn1—N3	2.124 (2)
Zn1—N4	2.088 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯N2i	0.88	2.33	3.202 (4)	169
N1—H1E⋯O2ii	0.88	2.36	3.181 (4)	155
N2—H2E⋯O2iii	0.88	2.28	3.116 (4)	159

Symmetry codes: (i) ; (ii) ; (iii) .