(Dicyanamido)[tris-(2-pyridylmeth-yl)amine]zinc(II) perchlorate.

In the title complex, [Zn(C(2)N(3))(C(18)H(18)N(4))]ClO(4), the Zn(II) ion has a slightly distorted trigonal-bipyramidal ZnN(5) coordination geometry. The crystal structure is stabilized by weak inter-molecular C-H⋯O and C-H⋯N hydrogen bonds. In addition, there are relatively close contacts between the O atoms of the perchlorate anion and symmetry-related pyridine rings [O⋯Cg = 3.179 (3) and 3.236 (3) Å, where Cg is the centroid of a pyridine ring], and between the terminal N atom of the dicyanamide ligand and pyridine rings [N⋯Cg = 3.381 (4)-3.761 (3) Å]. The central N atom of the dicyanamide ligand is disordered over two sites in an approximately 0.6:0.4 ratio.

Related literature

For related literature, see: Makowska-Grzyska et al. (2003 ▶); Sun et al. (2003 ▶); Martin et al. (2001 ▶).

Experimental

Crystal data

[Zn(C2N3)(C18H18N4)]ClO4

M = 521.23

Monoclinic,

a = 13.931 (2) Å

b = 10.8578 (18) Å

c = 14.653 (2) Å

β = 91.590 (3)°

V = 2215.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.27 mm−1

T = 298 (2) K

0.30 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.702, T max = 0.803

12346 measured reflections

4800 independent reflections

3352 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.106

S = 0.99

4800 reflections

308 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004741/lh2594sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004741/lh2594Isup2.hkl

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

[Zn(C2N3)(C18H18N4)]ClO4	F000 = 1064
Mr = 521.23	Dx = 1.563 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2616 reflections
a = 13.931 (2) Å	θ = 2.3–22.0º
b = 10.8578 (18) Å	µ = 1.27 mm−1
c = 14.653 (2) Å	T = 298 (2) K
β = 91.590 (3)º	Block, colorless
V = 2215.5 (6) Å3	0.30 × 0.20 × 0.18 mm
Z = 4

Bruker SMART APEX CCD diffractometer	4800 independent reflections
Radiation source: fine-focus sealed tube	3352 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.035
T = 298(2) K	θmax = 27.0º
φ and ω scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −15→17
Tmin = 0.702, Tmax = 0.803	k = −13→12
12346 measured reflections	l = −18→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.053P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
4800 reflections	Δρmax = 0.36 e Å−3
308 parameters	Δρmin = −0.25 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	Occ. (<1)
C1	0.0860 (2)	0.9139 (3)	0.2853 (2)	0.0612 (9)
H1	0.0337	0.8627	0.2947	0.073*
C2	0.1044 (3)	1.0115 (4)	0.3423 (2)	0.0697 (10)
H2	0.0648	1.0272	0.3910	0.084*
C3	0.1813 (3)	1.0854 (3)	0.3270 (2)	0.0674 (9)
H3	0.1952	1.1517	0.3654	0.081*
C4	0.2375 (2)	1.0607 (3)	0.2547 (2)	0.0545 (8)
H4	0.2894	1.1122	0.2439	0.065*
C5	0.14649 (19)	0.8927 (3)	0.21361 (19)	0.0461 (7)
C6	0.1355 (2)	0.7823 (3)	0.1528 (2)	0.0562 (8)
H6A	0.1669	0.7122	0.1816	0.067*
H6B	0.0678	0.7629	0.1445	0.067*
C7	0.1151 (2)	0.8761 (3)	0.0017 (2)	0.0629 (9)
H7A	0.0784	0.9345	0.0367	0.076*
H7B	0.0702	0.8217	−0.0301	0.076*
C8	0.1729 (2)	0.9441 (3)	−0.0664 (2)	0.0519 (7)
C9	0.1372 (3)	0.9713 (3)	−0.1530 (2)	0.0691 (9)
H9	0.0769	0.9431	−0.1722	0.083*
C10	0.1913 (4)	1.0397 (4)	−0.2098 (2)	0.0812 (11)
H10	0.1684	1.0590	−0.2683	0.097*
C11	0.2798 (3)	1.0797 (3)	−0.1801 (2)	0.0786 (11)
H11	0.3177	1.1267	−0.2180	0.094*
C12	0.3118 (3)	1.0497 (3)	−0.0937 (2)	0.0617 (8)
H12	0.3719	1.0774	−0.0736	0.074*
C13	0.2121 (2)	0.6901 (3)	0.0215 (2)	0.0628 (9)
H13A	0.2159	0.7016	−0.0439	0.075*
H13B	0.1676	0.6233	0.0324	0.075*
C14	0.3093 (2)	0.6574 (3)	0.0606 (2)	0.0554 (8)
C15	0.3413 (4)	0.5360 (3)	0.0654 (3)	0.0844 (12)
H15	0.3010	0.4718	0.0469	0.101*
C16	0.4314 (4)	0.5126 (4)	0.0972 (3)	0.1041 (15)
H16	0.4535	0.4318	0.1008	0.125*
C17	0.4900 (3)	0.6072 (4)	0.1240 (3)	0.0947 (14)
H17	0.5526	0.5922	0.1448	0.114*
C18	0.4545 (2)	0.7252 (3)	0.1195 (2)	0.0681 (9)
H18	0.4936	0.7899	0.1392	0.082*
C19	0.4657 (2)	1.1134 (3)	0.1232 (2)	0.0594 (8)
C20	0.5964 (3)	1.2341 (3)	0.1587 (2)	0.0670 (9)
Cl1	0.13251 (5)	0.26686 (7)	0.06625 (5)	0.0551 (2)
N1	0.25963 (17)	0.9822 (2)	−0.03743 (15)	0.0474 (6)
N2	0.22133 (15)	0.9657 (2)	0.19860 (14)	0.0425 (5)
N3	0.36571 (17)	0.7501 (2)	0.08790 (16)	0.0500 (6)
N4	0.17686 (15)	0.8038 (2)	0.06381 (15)	0.0461 (6)
N5	0.42095 (18)	1.0295 (3)	0.11270 (19)	0.0626 (7)
N6	0.6718 (3)	1.2592 (3)	0.1805 (2)	0.1036 (12)
N7	0.5015 (14)	1.214 (2)	0.157 (3)	0.066 (7)	0.40 (7)
N7'	0.5148 (16)	1.2179 (15)	0.116 (3)	0.100 (5)	0.60 (7)
O1	0.1054 (2)	0.3925 (2)	0.06831 (17)	0.0854 (8)
O2	0.08216 (17)	0.2017 (2)	0.13439 (16)	0.0821 (7)
O3	0.23268 (17)	0.2569 (3)	0.0827 (2)	0.0980 (8)
O4	0.1080 (2)	0.2177 (2)	−0.02084 (16)	0.0905 (8)
Zn1	0.30405 (2)	0.92245 (3)	0.08979 (2)	0.04138 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0467 (17)	0.086 (3)	0.0509 (19)	0.0100 (16)	0.0088 (14)	0.0197 (18)
C2	0.081 (3)	0.086 (3)	0.0423 (19)	0.024 (2)	0.0134 (17)	0.0048 (18)
C3	0.089 (3)	0.067 (2)	0.0456 (19)	0.0119 (19)	0.0039 (18)	−0.0042 (16)
C4	0.0615 (19)	0.056 (2)	0.0459 (18)	0.0023 (14)	−0.0017 (15)	0.0004 (14)
C5	0.0401 (15)	0.0575 (18)	0.0404 (16)	0.0022 (13)	−0.0029 (12)	0.0081 (13)
C6	0.0447 (17)	0.068 (2)	0.0564 (19)	−0.0167 (15)	0.0066 (14)	0.0053 (15)
C7	0.0424 (17)	0.090 (2)	0.056 (2)	−0.0105 (16)	−0.0095 (15)	0.0053 (18)
C8	0.0528 (18)	0.0588 (19)	0.0437 (17)	0.0085 (14)	−0.0041 (14)	0.0003 (14)
C9	0.083 (2)	0.076 (2)	0.048 (2)	0.0142 (19)	−0.0125 (18)	−0.0030 (18)
C10	0.123 (4)	0.075 (3)	0.045 (2)	0.025 (2)	−0.006 (2)	0.0083 (18)
C11	0.120 (3)	0.062 (2)	0.055 (2)	0.005 (2)	0.020 (2)	0.0158 (17)
C12	0.074 (2)	0.0515 (19)	0.061 (2)	−0.0001 (16)	0.0158 (17)	0.0026 (15)
C13	0.074 (2)	0.056 (2)	0.059 (2)	−0.0263 (17)	0.0047 (17)	−0.0095 (15)
C14	0.075 (2)	0.0442 (17)	0.0481 (17)	−0.0047 (15)	0.0153 (15)	−0.0035 (14)
C15	0.119 (4)	0.046 (2)	0.089 (3)	0.001 (2)	0.030 (3)	0.0011 (19)
C16	0.138 (4)	0.067 (3)	0.108 (4)	0.043 (3)	0.033 (3)	0.018 (3)
C17	0.090 (3)	0.100 (4)	0.095 (3)	0.048 (3)	0.007 (2)	0.012 (3)
C18	0.061 (2)	0.073 (2)	0.070 (2)	0.0125 (17)	0.0050 (18)	0.0036 (18)
C19	0.0489 (18)	0.0545 (18)	0.074 (2)	−0.0062 (12)	−0.0102 (16)	0.0012 (17)
C20	0.071 (2)	0.058 (2)	0.072 (2)	−0.0248 (18)	−0.0010 (19)	−0.0053 (17)
Cl1	0.0535 (4)	0.0568 (5)	0.0552 (5)	−0.0035 (3)	0.0042 (4)	0.0010 (4)
N1	0.0524 (14)	0.0476 (14)	0.0424 (13)	0.0022 (11)	0.0063 (11)	0.0037 (11)
N2	0.0419 (13)	0.0463 (13)	0.0391 (13)	0.0032 (10)	−0.0033 (10)	0.0028 (10)
N3	0.0524 (15)	0.0494 (14)	0.0484 (15)	0.0025 (11)	0.0044 (11)	0.0023 (11)
N4	0.0411 (13)	0.0553 (15)	0.0421 (13)	−0.0109 (11)	0.0025 (10)	0.0002 (11)
N5	0.0485 (15)	0.0609 (16)	0.0784 (19)	−0.0141 (11)	0.0000 (13)	−0.0056 (14)
N6	0.090 (2)	0.118 (3)	0.103 (3)	−0.050 (2)	0.010 (2)	−0.037 (2)
N7	0.060 (6)	0.040 (8)	0.096 (15)	−0.005 (5)	−0.014 (8)	0.007 (6)
N7'	0.089 (7)	0.082 (6)	0.128 (15)	−0.040 (5)	−0.042 (8)	0.052 (7)
O1	0.107 (2)	0.0644 (16)	0.0849 (19)	0.0212 (14)	0.0130 (15)	0.0035 (13)
O2	0.0737 (16)	0.1009 (19)	0.0720 (16)	−0.0049 (13)	0.0058 (13)	0.0369 (14)
O3	0.0550 (15)	0.0947 (19)	0.144 (2)	−0.0051 (13)	0.0035 (15)	0.0138 (17)
O4	0.110 (2)	0.098 (2)	0.0639 (16)	−0.0235 (16)	0.0170 (14)	−0.0221 (14)
Zn1	0.03599 (18)	0.0427 (2)	0.0454 (2)	−0.00542 (13)	0.00088 (13)	−0.00063 (14)

C1—C2	1.368 (5)	C13—C14	1.498 (4)
C1—C5	1.384 (4)	C13—H13A	0.9700
C1—H1	0.9300	C13—H13B	0.9700
C2—C3	1.362 (5)	C14—N3	1.332 (4)
C2—H2	0.9300	C14—C15	1.392 (5)
C3—C4	1.362 (4)	C15—C16	1.352 (6)
C3—H3	0.9300	C15—H15	0.9300
C4—N2	1.334 (3)	C16—C17	1.363 (6)
C4—H4	0.9300	C16—H16	0.9300
C5—N2	1.333 (3)	C17—C18	1.374 (5)
C5—C6	1.499 (4)	C17—H17	0.9300
C6—N4	1.458 (3)	C18—N3	1.336 (4)
C6—H6A	0.9700	C18—H18	0.9300
C6—H6B	0.9700	C19—N5	1.112 (4)
C7—N4	1.463 (4)	C19—N7	1.294 (17)
C7—C8	1.495 (4)	C19—N7'	1.331 (14)
C7—H7A	0.9700	C20—N6	1.122 (4)
C7—H7B	0.9700	C20—N7'	1.298 (16)
C8—N1	1.335 (4)	C20—N7	1.34 (2)
C8—C9	1.382 (4)	Cl1—O3	1.414 (2)
C9—C10	1.359 (5)	Cl1—O4	1.416 (2)
C9—H9	0.9300	Cl1—O1	1.416 (2)
C10—C11	1.367 (6)	Cl1—O2	1.424 (2)
C10—H10	0.9300	N1—Zn1	2.053 (2)
C11—C12	1.369 (5)	N2—Zn1	2.048 (2)
C11—H11	0.9300	N3—Zn1	2.059 (2)
C12—N1	1.334 (4)	N4—Zn1	2.215 (2)
C12—H12	0.9300	N5—Zn1	2.021 (3)
C13—N4	1.472 (4)
C2—C1—C5	119.0 (3)	C16—C15—C14	119.3 (4)
C2—C1—H1	120.5	C16—C15—H15	120.4
C5—C1—H1	120.5	C14—C15—H15	120.4
C3—C2—C1	119.4 (3)	C15—C16—C17	120.0 (4)
C3—C2—H2	120.3	C15—C16—H16	120.0
C1—C2—H2	120.3	C17—C16—H16	120.0
C2—C3—C4	118.9 (3)	C16—C17—C18	118.5 (4)
C2—C3—H3	120.5	C16—C17—H17	120.7
C4—C3—H3	120.5	C18—C17—H17	120.7
N2—C4—C3	122.7 (3)	N3—C18—C17	122.3 (4)
N2—C4—H4	118.6	N3—C18—H18	118.9
C3—C4—H4	118.6	C17—C18—H18	118.9
N2—C5—C1	121.4 (3)	N5—C19—N7	162.3 (19)
N2—C5—C6	116.4 (2)	N5—C19—N7'	166.9 (17)
C1—C5—C6	122.0 (3)	N6—C20—N7'	166.3 (18)
N4—C6—C5	111.5 (2)	N6—C20—N7	163.6 (17)
N4—C6—H6A	109.3	O3—Cl1—O4	109.71 (18)
C5—C6—H6A	109.3	O3—Cl1—O1	109.44 (17)
N4—C6—H6B	109.3	O4—Cl1—O1	108.92 (16)
C5—C6—H6B	109.3	O3—Cl1—O2	110.20 (16)
H6A—C6—H6B	108.0	O4—Cl1—O2	109.48 (16)
N4—C7—C8	111.2 (2)	O1—Cl1—O2	109.07 (16)
N4—C7—H7A	109.4	C12—N1—C8	118.5 (3)
C8—C7—H7A	109.4	C12—N1—Zn1	125.4 (2)
N4—C7—H7B	109.4	C8—N1—Zn1	115.97 (19)
C8—C7—H7B	109.4	C5—N2—C4	118.6 (3)
H7A—C7—H7B	108.0	C5—N2—Zn1	116.86 (19)
N1—C8—C9	121.7 (3)	C4—N2—Zn1	124.6 (2)
N1—C8—C7	116.1 (2)	C14—N3—C18	118.9 (3)
C9—C8—C7	122.1 (3)	C14—N3—Zn1	116.6 (2)
C10—C9—C8	119.2 (4)	C18—N3—Zn1	124.2 (2)
C10—C9—H9	120.4	C6—N4—C7	113.7 (2)
C8—C9—H9	120.4	C6—N4—C13	112.7 (2)
C9—C10—C11	119.3 (3)	C7—N4—C13	112.7 (2)
C9—C10—H10	120.4	C6—N4—Zn1	105.89 (16)
C11—C10—H10	120.4	C7—N4—Zn1	104.41 (17)
C10—C11—C12	119.1 (3)	C13—N4—Zn1	106.58 (17)
C10—C11—H11	120.4	C19—N5—Zn1	160.0 (3)
C12—C11—H11	120.4	C19—N7—C20	120.9 (14)
N1—C12—C11	122.2 (3)	C20—N7'—C19	121.4 (13)
N1—C12—H12	118.9	N5—Zn1—N2	101.94 (10)
C11—C12—H12	118.9	N5—Zn1—N1	100.96 (11)
N4—C13—C14	110.3 (2)	N2—Zn1—N1	118.19 (9)
N4—C13—H13A	109.6	N5—Zn1—N3	100.98 (10)
C14—C13—H13A	109.6	N2—Zn1—N3	117.58 (9)
N4—C13—H13B	109.6	N1—Zn1—N3	112.99 (9)
C14—C13—H13B	109.6	N5—Zn1—N4	179.41 (10)
H13A—C13—H13B	108.1	N2—Zn1—N4	78.60 (9)
N3—C14—C15	121.0 (3)	N1—Zn1—N4	78.95 (9)
N3—C14—C13	117.1 (3)	N3—Zn1—N4	78.55 (9)
C15—C14—C13	121.9 (3)
C5—C1—C2—C3	0.2 (5)	C14—C13—N4—Zn1	34.9 (3)
C1—C2—C3—C4	0.6 (5)	N7—C19—N5—Zn1	63 (5)
C2—C3—C4—N2	−1.0 (5)	N7'—C19—N5—Zn1	−71 (7)
C2—C1—C5—N2	−0.6 (4)	N5—C19—N7—C20	138.7 (19)
C2—C1—C5—C6	175.2 (3)	N7'—C19—N7—C20	−61 (3)
N2—C5—C6—N4	−27.9 (3)	N6—C20—N7—C19	−134 (2)
C1—C5—C6—N4	156.1 (3)	N7'—C20—N7—C19	65 (3)
N4—C7—C8—N1	−33.0 (4)	N6—C20—N7'—C19	141 (3)
N4—C7—C8—C9	150.0 (3)	N7—C20—N7'—C19	−62 (2)
N1—C8—C9—C10	−0.7 (5)	N5—C19—N7'—C20	−142 (3)
C7—C8—C9—C10	176.1 (3)	N7—C19—N7'—C20	66 (3)
C8—C9—C10—C11	0.1 (6)	C19—N5—Zn1—N2	−60.5 (8)
C9—C10—C11—C12	0.1 (6)	C19—N5—Zn1—N1	61.7 (8)
C10—C11—C12—N1	0.2 (5)	C19—N5—Zn1—N3	178.0 (8)
N4—C13—C14—N3	−30.8 (4)	C5—N2—Zn1—N5	−167.30 (19)
N4—C13—C14—C15	151.5 (3)	C4—N2—Zn1—N5	12.5 (2)
N3—C14—C15—C16	−0.8 (5)	C5—N2—Zn1—N1	83.2 (2)
C13—C14—C15—C16	176.8 (4)	C4—N2—Zn1—N1	−97.0 (2)
C14—C15—C16—C17	−0.1 (7)	C5—N2—Zn1—N3	−58.0 (2)
C15—C16—C17—C18	1.3 (7)	C4—N2—Zn1—N3	121.8 (2)
C16—C17—C18—N3	−1.6 (6)	C5—N2—Zn1—N4	12.47 (18)
C11—C12—N1—C8	−0.8 (5)	C4—N2—Zn1—N4	−167.7 (2)
C11—C12—N1—Zn1	175.7 (2)	C12—N1—Zn1—N5	14.7 (3)
C9—C8—N1—C12	1.0 (4)	C8—N1—Zn1—N5	−168.7 (2)
C7—C8—N1—C12	−176.0 (3)	C12—N1—Zn1—N2	124.8 (2)
C9—C8—N1—Zn1	−175.8 (2)	C8—N1—Zn1—N2	−58.7 (2)
C7—C8—N1—Zn1	7.2 (3)	C12—N1—Zn1—N3	−92.3 (2)
C1—C5—N2—C4	0.2 (4)	C8—N1—Zn1—N3	84.2 (2)
C6—C5—N2—C4	−175.8 (2)	C12—N1—Zn1—N4	−164.7 (3)
C1—C5—N2—Zn1	−180.0 (2)	C8—N1—Zn1—N4	11.9 (2)
C6—C5—N2—Zn1	4.0 (3)	C14—N3—Zn1—N5	−170.4 (2)
C3—C4—N2—C5	0.6 (4)	C18—N3—Zn1—N5	15.8 (3)
C3—C4—N2—Zn1	−179.2 (2)	C14—N3—Zn1—N2	79.8 (2)
C15—C14—N3—C18	0.6 (4)	C18—N3—Zn1—N2	−94.1 (3)
C13—C14—N3—C18	−177.2 (3)	C14—N3—Zn1—N1	−63.4 (2)
C15—C14—N3—Zn1	−173.6 (2)	C18—N3—Zn1—N1	122.8 (2)
C13—C14—N3—Zn1	8.6 (3)	C14—N3—Zn1—N4	9.3 (2)
C17—C18—N3—C14	0.7 (5)	C18—N3—Zn1—N4	−164.6 (3)
C17—C18—N3—Zn1	174.4 (3)	C6—N4—Zn1—N2	−25.66 (18)
C5—C6—N4—C7	−79.4 (3)	C7—N4—Zn1—N2	94.61 (19)
C5—C6—N4—C13	150.8 (2)	C13—N4—Zn1—N2	−145.91 (19)
C5—C6—N4—Zn1	34.7 (3)	C6—N4—Zn1—N1	−147.68 (19)
C8—C7—N4—C6	153.5 (3)	C7—N4—Zn1—N1	−27.42 (18)
C8—C7—N4—C13	−76.7 (3)	C13—N4—Zn1—N1	92.06 (19)
C8—C7—N4—Zn1	38.6 (3)	C6—N4—Zn1—N3	95.86 (18)
C14—C13—N4—C6	−80.8 (3)	C7—N4—Zn1—N3	−143.9 (2)
C14—C13—N4—C7	148.9 (2)	C13—N4—Zn1—N3	−24.39 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4i	0.93	2.53	3.272 (4)	138
C7—H7B···O2ii	0.97	2.59	3.455 (4)	148
C10—H10···O1iii	0.93	2.58	3.511 (5)	179
C13—H13A···N6iv	0.97	2.61	3.457 (5)	146
C16—H16···N7'v	0.93	2.48	3.412 (18)	178

N1—Zn1	2.053 (2)
N2—Zn1	2.048 (2)
N3—Zn1	2.059 (2)
N4—Zn1	2.215 (2)
N5—Zn1	2.021 (3)

N5—Zn1—N2	101.94 (10)
N5—Zn1—N1	100.96 (11)
N2—Zn1—N1	118.19 (9)
N5—Zn1—N3	100.98 (10)
N2—Zn1—N3	117.58 (9)
N1—Zn1—N3	112.99 (9)
N5—Zn1—N4	179.41 (10)
N2—Zn1—N4	78.60 (9)
N1—Zn1—N4	78.95 (9)
N3—Zn1—N4	78.55 (9)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O4i	0.93	2.53	3.272 (4)	138
C7—H7B⋯O2ii	0.97	2.59	3.455 (4)	148
C10—H10⋯O1iii	0.93	2.58	3.511 (5)	179
C13—H13A⋯N6iv	0.97	2.61	3.457 (5)	146
C16—H16⋯N7′v	0.93	2.48	3.412 (18)	178

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