Dichloridobis{N,N-diethyl-4-[(pyridin-2-yl-κN)diazen-yl]aniline}zinc.

In the title complex, [ZnCl(2)(C(15)H(18)N(4))(2)], the Zn(II) cation is coordinated by two N atoms from the pyridine rings of two unidentate N,N-diethyl-4-[(pyridin-2-yl)diazen-yl]aniline ligands and two Cl atoms, resulting in a distorted tetra-hedral geometry. The ligands are mutually transoid with respect to the metal atom. Weak inter-molecular C-H⋯Cl hydrogen bonds and π-π inter-actions, with centroid-centroid distances of 3.8452 (14) and 3.9932 (14) Å, are found in the crystal packing.

Related literature

For background to azo complexes, see: Arslan (2007 ▶); Santra et al. (2001 ▶); Peacock et al. (2007 ▶); Ohashi et al. (2003 ▶). For applications of azo compounds, see: Millington et al. (2007 ▶); Hallas & Choi (1999 ▶); Ho et al. (1995 ▶); Sharma et al. (2008 ▶). For their photochromic properties, see: Baena et al. (1994 ▶). For structures of related azoimine complexes, see: Leesakul et al. (2010 ▶); Nag et al. (2001 ▶); Pramanik & Das (2010 ▶); Steffen & Palenik (1976 ▶).

Experimental

Crystal data

[ZnCl2(C15H18N4)2]

M = 644.96

Monoclinic,

a = 13.4058 (6) Å

b = 13.8797 (6) Å

c = 16.8157 (8) Å

β = 100.562 (1)°

V = 3075.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.01 mm−1

T = 100 K

0.17 × 0.17 × 0.06 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.780, T max = 1.000

32570 measured reflections

5410 independent reflections

4547 reflections with I > 2s(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.086

S = 1.06

5410 reflections

374 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811022884/fj2423sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022884/fj2423Isup2.hkl

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

[ZnCl2(C15H18N4)2]	F(000) = 1344
Mr = 644.96	Dx = 1.393 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5833 reflections
a = 13.4058 (6) Å	θ = 2.3–24.9°
b = 13.8797 (6) Å	µ = 1.01 mm−1
c = 16.8157 (8) Å	T = 100 K
β = 100.562 (1)°	Block, red brown
V = 3075.9 (2) Å3	0.17 × 0.17 × 0.06 mm
Z = 4

Bruker APEX CCD area-detector diffractometer	5410 independent reflections
Radiation source: fine-focus sealed tube	4547 reflections with I > 2s(I)
graphite	Rint = 0.050
Frames, each covering 0.3 ° in ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −15→15
Tmin = 0.780, Tmax = 1.000	k = −16→16
32570 measured reflections	l = −19→19

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) = 0.086	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.042P)2 + 1.4983P] where P = (Fo2 + 2Fc2)/3
5410 reflections	(Δ/σ)max = 0.002
374 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.27 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 > 2σ (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	0.22361 (2)	1.268175 (19)	0.199133 (15)	0.01635 (9)
Cl1	0.33540 (5)	1.35648 (4)	0.28631 (3)	0.02473 (15)
Cl2	0.10979 (5)	1.36055 (4)	0.11562 (4)	0.02345 (15)
N1	0.14219 (14)	1.19205 (13)	0.27007 (11)	0.0166 (4)
N2	0.11954 (14)	1.08164 (13)	0.16762 (11)	0.0183 (4)
N3	0.09170 (14)	0.99507 (14)	0.14720 (12)	0.0193 (4)
N4	0.15013 (15)	0.85544 (14)	−0.15184 (12)	0.0197 (4)
N5	0.30591 (14)	1.20492 (13)	0.12234 (11)	0.0162 (4)
N6	0.35399 (14)	1.09944 (13)	0.22628 (11)	0.0175 (4)
N7	0.40540 (14)	1.02387 (14)	0.25039 (11)	0.0191 (4)
N8	0.38830 (15)	0.89031 (14)	0.56015 (11)	0.0207 (4)
C1	0.13247 (17)	1.22457 (17)	0.34345 (14)	0.0191 (5)
H1	0.1592	1.2862	0.3602	0.023*
C2	0.08522 (17)	1.17201 (18)	0.39560 (14)	0.0212 (5)
H2	0.0804	1.1962	0.4476	0.025*
C3	0.04487 (17)	1.08254 (18)	0.36986 (14)	0.0217 (5)
H3	0.0132	1.0441	0.4048	0.026*
C4	0.05098 (17)	1.04982 (17)	0.29372 (14)	0.0204 (5)
H4	0.0208	0.9903	0.2746	0.025*
C5	0.10238 (16)	1.10573 (16)	0.24487 (14)	0.0166 (5)
C6	0.10811 (17)	0.96618 (16)	0.07189 (14)	0.0186 (5)
C7	0.07776 (18)	0.87198 (17)	0.04831 (15)	0.0219 (5)
H7	0.0478	0.8329	0.0839	0.026*
C8	0.09029 (18)	0.83498 (17)	−0.02471 (14)	0.0213 (5)
H8	0.0678	0.7714	−0.0392	0.026*
C9	0.13627 (17)	0.89031 (17)	−0.07878 (14)	0.0184 (5)
C10	0.16746 (18)	0.98555 (17)	−0.05428 (14)	0.0194 (5)
H10	0.1995	1.0245	−0.0887	0.023*
C11	0.15197 (17)	1.02167 (17)	0.01785 (14)	0.0196 (5)
H11	0.1714	1.0862	0.0318	0.024*
C12	0.21799 (18)	0.90415 (18)	−0.19791 (15)	0.0233 (5)
H12A	0.1994	0.9732	−0.2032	0.028*
H12B	0.2079	0.8764	−0.2530	0.028*
C13	0.32931 (19)	0.89580 (19)	−0.15950 (15)	0.0270 (6)
H13A	0.3398	0.9221	−0.1045	0.040*
H13B	0.3704	0.9320	−0.1918	0.040*
H13C	0.3496	0.8279	−0.1574	0.040*
C14	0.1117 (2)	0.76118 (18)	−0.18226 (16)	0.0277 (6)
H14A	0.0902	0.7650	−0.2417	0.033*
H14B	0.0512	0.7451	−0.1588	0.033*
C15	0.1883 (2)	0.6822 (2)	−0.1625 (2)	0.0539 (10)
H15A	0.2444	0.6931	−0.1915	0.081*
H15B	0.1562	0.6201	−0.1789	0.081*
H15C	0.2145	0.6816	−0.1041	0.081*
C16	0.30213 (18)	1.23720 (17)	0.04651 (14)	0.0193 (5)
H16	0.2644	1.2940	0.0300	0.023*
C17	0.35077 (17)	1.19130 (17)	−0.00828 (14)	0.0211 (5)
H17	0.3466	1.2155	−0.0616	0.025*
C18	0.40618 (18)	1.10855 (18)	0.01682 (14)	0.0221 (5)
H18	0.4401	1.0751	−0.0197	0.026*
C19	0.41197 (17)	1.07505 (17)	0.09476 (14)	0.0206 (5)
H19	0.4504	1.0191	0.1129	0.025*
C20	0.36016 (17)	1.12516 (16)	0.14622 (13)	0.0167 (5)
C21	0.39913 (17)	0.99451 (17)	0.32815 (14)	0.0187 (5)
C22	0.45412 (18)	0.91200 (17)	0.35774 (14)	0.0208 (5)
H22	0.4943	0.8800	0.3249	0.025*
C23	0.45074 (17)	0.87670 (17)	0.43350 (14)	0.0207 (5)
H23	0.4885	0.8205	0.4519	0.025*
C24	0.39216 (17)	0.92230 (16)	0.48482 (14)	0.0188 (5)
C25	0.33610 (18)	1.00572 (17)	0.45299 (14)	0.0200 (5)
H25	0.2948	1.0377	0.4850	0.024*
C26	0.34047 (18)	1.04044 (17)	0.37802 (14)	0.0194 (5)
H26	0.3032	1.0967	0.3591	0.023*
C27	0.31848 (19)	0.93302 (18)	0.60798 (14)	0.0245 (6)
H27A	0.3236	1.0041	0.6054	0.029*
H27B	0.3399	0.9136	0.6652	0.029*
C28	0.20876 (19)	0.9040 (2)	0.57998 (16)	0.0312 (6)
H28A	0.1865	0.9235	0.5235	0.047*
H28B	0.1664	0.9357	0.6139	0.047*
H28C	0.2024	0.8339	0.5844	0.047*
C29	0.44691 (19)	0.80678 (17)	0.59611 (15)	0.0239 (6)
H29A	0.4663	0.8172	0.6552	0.029*
H29B	0.5102	0.8027	0.5738	0.029*
C30	0.3912 (2)	0.71195 (18)	0.5815 (2)	0.0381 (7)
H30A	0.3286	0.7150	0.6037	0.057*
H30B	0.4344	0.6600	0.6081	0.057*
H30C	0.3744	0.6994	0.5232	0.057*

	U11	U22	U33	U12	U13	U23
Zn1	0.01989 (16)	0.01422 (15)	0.01534 (15)	0.00023 (11)	0.00428 (11)	0.00035 (11)
Cl1	0.0290 (3)	0.0241 (3)	0.0210 (3)	−0.0076 (3)	0.0041 (3)	−0.0036 (2)
Cl2	0.0261 (3)	0.0200 (3)	0.0243 (3)	0.0059 (2)	0.0047 (3)	0.0049 (2)
N1	0.0165 (10)	0.0162 (10)	0.0170 (10)	0.0029 (8)	0.0026 (8)	0.0020 (8)
N2	0.0170 (10)	0.0169 (10)	0.0204 (10)	0.0005 (8)	0.0013 (8)	−0.0017 (8)
N3	0.0181 (10)	0.0159 (10)	0.0230 (11)	0.0003 (8)	0.0017 (8)	−0.0014 (8)
N4	0.0200 (10)	0.0182 (10)	0.0205 (10)	−0.0021 (8)	0.0024 (8)	−0.0033 (8)
N5	0.0169 (10)	0.0143 (10)	0.0173 (10)	−0.0024 (8)	0.0029 (8)	−0.0008 (8)
N6	0.0170 (10)	0.0163 (10)	0.0187 (10)	−0.0011 (8)	0.0021 (8)	0.0009 (8)
N7	0.0180 (10)	0.0170 (10)	0.0215 (10)	0.0008 (8)	0.0010 (8)	0.0001 (8)
N8	0.0229 (11)	0.0183 (10)	0.0208 (11)	0.0040 (9)	0.0040 (9)	0.0037 (9)
C1	0.0162 (12)	0.0191 (12)	0.0210 (13)	0.0032 (10)	0.0011 (10)	−0.0005 (10)
C2	0.0180 (12)	0.0288 (14)	0.0171 (12)	0.0060 (11)	0.0042 (10)	0.0015 (10)
C3	0.0156 (12)	0.0256 (13)	0.0247 (13)	0.0022 (10)	0.0059 (10)	0.0085 (11)
C4	0.0139 (12)	0.0167 (12)	0.0299 (14)	−0.0002 (10)	0.0022 (10)	0.0014 (10)
C5	0.0133 (12)	0.0150 (12)	0.0202 (12)	0.0015 (9)	−0.0001 (9)	0.0022 (10)
C6	0.0160 (12)	0.0177 (12)	0.0213 (12)	0.0006 (10)	0.0017 (10)	−0.0017 (10)
C7	0.0224 (13)	0.0177 (12)	0.0259 (13)	−0.0030 (10)	0.0056 (10)	0.0014 (10)
C8	0.0221 (13)	0.0141 (12)	0.0277 (13)	−0.0020 (10)	0.0047 (10)	−0.0021 (10)
C9	0.0123 (11)	0.0186 (12)	0.0224 (12)	0.0019 (10)	−0.0015 (9)	0.0000 (10)
C10	0.0191 (12)	0.0189 (12)	0.0196 (12)	−0.0035 (10)	0.0022 (10)	0.0022 (10)
C11	0.0172 (12)	0.0141 (12)	0.0260 (13)	−0.0015 (10)	0.0001 (10)	−0.0005 (10)
C12	0.0248 (14)	0.0237 (13)	0.0210 (13)	−0.0022 (11)	0.0035 (10)	−0.0018 (10)
C13	0.0260 (14)	0.0278 (14)	0.0279 (14)	−0.0030 (11)	0.0072 (11)	−0.0005 (11)
C14	0.0265 (14)	0.0237 (14)	0.0326 (15)	−0.0047 (11)	0.0049 (11)	−0.0080 (11)
C15	0.0332 (17)	0.0193 (15)	0.103 (3)	−0.0011 (13)	−0.0038 (18)	−0.0061 (17)
C16	0.0194 (12)	0.0182 (12)	0.0203 (12)	−0.0038 (10)	0.0033 (10)	0.0014 (10)
C17	0.0208 (13)	0.0247 (13)	0.0182 (12)	−0.0094 (11)	0.0048 (10)	0.0022 (10)
C18	0.0204 (13)	0.0236 (13)	0.0241 (13)	−0.0039 (11)	0.0087 (10)	−0.0074 (11)
C19	0.0166 (12)	0.0204 (12)	0.0256 (13)	−0.0011 (10)	0.0056 (10)	−0.0022 (10)
C20	0.0159 (12)	0.0149 (12)	0.0193 (12)	−0.0042 (10)	0.0031 (9)	−0.0009 (9)
C21	0.0165 (12)	0.0186 (12)	0.0204 (12)	−0.0004 (10)	0.0015 (10)	0.0000 (10)
C22	0.0184 (12)	0.0207 (13)	0.0239 (13)	0.0024 (10)	0.0055 (10)	−0.0005 (10)
C23	0.0176 (12)	0.0171 (12)	0.0265 (13)	0.0051 (10)	0.0020 (10)	0.0022 (10)
C24	0.0186 (12)	0.0177 (12)	0.0187 (12)	−0.0010 (10)	−0.0002 (10)	−0.0002 (10)
C25	0.0203 (12)	0.0183 (12)	0.0214 (12)	0.0026 (10)	0.0036 (10)	−0.0022 (10)
C26	0.0196 (13)	0.0153 (12)	0.0221 (12)	0.0024 (10)	0.0005 (10)	0.0014 (10)
C27	0.0313 (14)	0.0255 (13)	0.0175 (12)	0.0064 (11)	0.0068 (11)	0.0009 (10)
C28	0.0270 (15)	0.0318 (15)	0.0367 (16)	0.0058 (12)	0.0109 (12)	0.0037 (12)
C29	0.0267 (14)	0.0232 (13)	0.0211 (13)	0.0051 (11)	0.0026 (10)	0.0043 (10)
C30	0.0363 (17)	0.0194 (14)	0.058 (2)	0.0035 (12)	0.0057 (14)	0.0040 (13)

Zn1—N5	2.0439 (19)	C12—H12B	0.9900
Zn1—N1	2.0513 (19)	C13—H13A	0.9800
Zn1—Cl1	2.2565 (6)	C13—H13B	0.9800
Zn1—Cl2	2.2713 (6)	C13—H13C	0.9800
N1—C1	1.343 (3)	C14—C15	1.498 (4)
N1—C5	1.348 (3)	C14—H14A	0.9900
N2—N3	1.286 (3)	C14—H14B	0.9900
N2—C5	1.401 (3)	C15—H15A	0.9800
N3—C6	1.384 (3)	C15—H15B	0.9800
N4—C9	1.364 (3)	C15—H15C	0.9800
N4—C14	1.463 (3)	C16—C17	1.378 (3)
N4—C12	1.464 (3)	C16—H16	0.9500
N5—C16	1.344 (3)	C17—C18	1.391 (3)
N5—C20	1.345 (3)	C17—H17	0.9500
N6—N7	1.280 (3)	C18—C19	1.379 (3)
N6—C20	1.410 (3)	C18—H18	0.9500
N7—C21	1.387 (3)	C19—C20	1.391 (3)
N8—C24	1.352 (3)	C19—H19	0.9500
N8—C27	1.466 (3)	C21—C22	1.403 (3)
N8—C29	1.467 (3)	C21—C26	1.404 (3)
C1—C2	1.381 (3)	C22—C23	1.373 (3)
C1—H1	0.9500	C22—H22	0.9500
C2—C3	1.391 (3)	C23—C24	1.418 (3)
C2—H2	0.9500	C23—H23	0.9500
C3—C4	1.375 (3)	C24—C25	1.430 (3)
C3—H3	0.9500	C25—C26	1.361 (3)
C4—C5	1.400 (3)	C25—H25	0.9500
C4—H4	0.9500	C26—H26	0.9500
C6—C11	1.400 (3)	C27—C28	1.514 (4)
C6—C7	1.405 (3)	C27—H27A	0.9900
C7—C8	1.369 (3)	C27—H27B	0.9900
C7—H7	0.9500	C28—H28A	0.9800
C8—C9	1.415 (3)	C28—H28B	0.9800
C8—H8	0.9500	C28—H28C	0.9800
C9—C10	1.424 (3)	C29—C30	1.511 (4)
C10—C11	1.363 (3)	C29—H29A	0.9900
C10—H10	0.9500	C29—H29B	0.9900
C11—H11	0.9500	C30—H30A	0.9800
C12—C13	1.518 (3)	C30—H30B	0.9800
C12—H12A	0.9900	C30—H30C	0.9800
N5—Zn1—N1	123.54 (8)	N4—C14—H14A	108.9
N5—Zn1—Cl1	105.82 (5)	C15—C14—H14A	108.9
N1—Zn1—Cl1	105.24 (6)	N4—C14—H14B	108.9
N5—Zn1—Cl2	103.36 (6)	C15—C14—H14B	108.9
N1—Zn1—Cl2	106.35 (5)	H14A—C14—H14B	107.8
Cl1—Zn1—Cl2	112.70 (2)	C14—C15—H15A	109.5
C1—N1—C5	119.2 (2)	C14—C15—H15B	109.5
C1—N1—Zn1	120.86 (16)	H15A—C15—H15B	109.5
C5—N1—Zn1	119.82 (15)	C14—C15—H15C	109.5
N3—N2—C5	112.43 (19)	H15A—C15—H15C	109.5
N2—N3—C6	115.34 (19)	H15B—C15—H15C	109.5
C9—N4—C14	122.3 (2)	N5—C16—C17	122.7 (2)
C9—N4—C12	120.86 (19)	N5—C16—H16	118.7
C14—N4—C12	116.16 (19)	C17—C16—H16	118.7
C16—N5—C20	118.8 (2)	C16—C17—C18	118.1 (2)
C16—N5—Zn1	121.70 (16)	C16—C17—H17	121.0
C20—N5—Zn1	119.34 (15)	C18—C17—H17	121.0
N7—N6—C20	112.80 (18)	C19—C18—C17	120.0 (2)
N6—N7—C21	114.67 (19)	C19—C18—H18	120.0
C24—N8—C27	121.26 (19)	C17—C18—H18	120.0
C24—N8—C29	122.4 (2)	C18—C19—C20	118.4 (2)
C27—N8—C29	116.16 (19)	C18—C19—H19	120.8
N1—C1—C2	122.6 (2)	C20—C19—H19	120.8
N1—C1—H1	118.7	N5—C20—C19	122.0 (2)
C2—C1—H1	118.7	N5—C20—N6	111.74 (19)
C1—C2—C3	118.1 (2)	C19—C20—N6	126.2 (2)
C1—C2—H2	120.9	N7—C21—C22	117.1 (2)
C3—C2—H2	120.9	N7—C21—C26	124.6 (2)
C4—C3—C2	119.9 (2)	C22—C21—C26	118.3 (2)
C4—C3—H3	120.1	C23—C22—C21	121.0 (2)
C2—C3—H3	120.1	C23—C22—H22	119.5
C3—C4—C5	118.9 (2)	C21—C22—H22	119.5
C3—C4—H4	120.6	C22—C23—C24	121.4 (2)
C5—C4—H4	120.6	C22—C23—H23	119.3
N1—C5—C4	121.2 (2)	C24—C23—H23	119.3
N1—C5—N2	112.38 (19)	N8—C24—C23	123.0 (2)
C4—C5—N2	126.5 (2)	N8—C24—C25	120.6 (2)
N3—C6—C11	126.2 (2)	C23—C24—C25	116.4 (2)
N3—C6—C7	116.2 (2)	C26—C25—C24	121.6 (2)
C11—C6—C7	117.6 (2)	C26—C25—H25	119.2
C8—C7—C6	121.7 (2)	C24—C25—H25	119.2
C8—C7—H7	119.2	C25—C26—C21	121.1 (2)
C6—C7—H7	119.2	C25—C26—H26	119.4
C7—C8—C9	120.8 (2)	C21—C26—H26	119.4
C7—C8—H8	119.6	N8—C27—C28	113.8 (2)
C9—C8—H8	119.6	N8—C27—H27A	108.8
N4—C9—C8	122.2 (2)	C28—C27—H27A	108.8
N4—C9—C10	120.6 (2)	N8—C27—H27B	108.8
C8—C9—C10	117.2 (2)	C28—C27—H27B	108.8
C11—C10—C9	120.9 (2)	H27A—C27—H27B	107.7
C11—C10—H10	119.5	C27—C28—H28A	109.5
C9—C10—H10	119.5	C27—C28—H28B	109.5
C10—C11—C6	121.7 (2)	H28A—C28—H28B	109.5
C10—C11—H11	119.1	C27—C28—H28C	109.5
C6—C11—H11	119.1	H28A—C28—H28C	109.5
N4—C12—C13	113.4 (2)	H28B—C28—H28C	109.5
N4—C12—H12A	108.9	N8—C29—C30	114.2 (2)
C13—C12—H12A	108.9	N8—C29—H29A	108.7
N4—C12—H12B	108.9	C30—C29—H29A	108.7
C13—C12—H12B	108.9	N8—C29—H29B	108.7
H12A—C12—H12B	107.7	C30—C29—H29B	108.7
C12—C13—H13A	109.5	H29A—C29—H29B	107.6
C12—C13—H13B	109.5	C29—C30—H30A	109.5
H13A—C13—H13B	109.5	C29—C30—H30B	109.5
C12—C13—H13C	109.5	H30A—C30—H30B	109.5
H13A—C13—H13C	109.5	C29—C30—H30C	109.5
H13B—C13—H13C	109.5	H30A—C30—H30C	109.5
N4—C14—C15	113.2 (2)	H30B—C30—H30C	109.5
N5—Zn1—N1—C1	146.45 (16)	C9—C10—C11—C6	2.1 (4)
Cl1—Zn1—N1—C1	25.15 (18)	N3—C6—C11—C10	178.1 (2)
Cl2—Zn1—N1—C1	−94.64 (17)	C7—C6—C11—C10	−1.7 (3)
N5—Zn1—N1—C5	−29.95 (19)	C9—N4—C12—C13	69.6 (3)
Cl1—Zn1—N1—C5	−151.25 (15)	C14—N4—C12—C13	−101.3 (2)
Cl2—Zn1—N1—C5	88.96 (16)	C9—N4—C14—C15	−93.7 (3)
C5—N2—N3—C6	−179.03 (19)	C12—N4—C14—C15	77.0 (3)
N1—Zn1—N5—C16	135.03 (17)	C20—N5—C16—C17	0.7 (3)
Cl1—Zn1—N5—C16	−103.94 (17)	Zn1—N5—C16—C17	−174.90 (17)
Cl2—Zn1—N5—C16	14.72 (18)	N5—C16—C17—C18	−0.3 (3)
N1—Zn1—N5—C20	−40.56 (19)	C16—C17—C18—C19	−0.5 (3)
Cl1—Zn1—N5—C20	80.47 (16)	C17—C18—C19—C20	0.9 (3)
Cl2—Zn1—N5—C20	−160.87 (15)	C16—N5—C20—C19	−0.3 (3)
C20—N6—N7—C21	−178.30 (19)	Zn1—N5—C20—C19	175.45 (17)
C5—N1—C1—C2	1.6 (3)	C16—N5—C20—N6	−178.30 (19)
Zn1—N1—C1—C2	−174.77 (17)	Zn1—N5—C20—N6	−2.6 (2)
N1—C1—C2—C3	−1.1 (3)	C18—C19—C20—N5	−0.5 (3)
C1—C2—C3—C4	−1.3 (3)	C18—C19—C20—N6	177.2 (2)
C2—C3—C4—C5	3.0 (3)	N7—N6—C20—N5	−179.76 (18)
C1—N1—C5—C4	0.2 (3)	N7—N6—C20—C19	2.3 (3)
Zn1—N1—C5—C4	176.66 (16)	N6—N7—C21—C22	−179.9 (2)
C1—N1—C5—N2	−179.48 (19)	N6—N7—C21—C26	1.3 (3)
Zn1—N1—C5—N2	−3.0 (2)	N7—C21—C22—C23	−178.7 (2)
C3—C4—C5—N1	−2.5 (3)	C26—C21—C22—C23	0.1 (3)
C3—C4—C5—N2	177.1 (2)	C21—C22—C23—C24	−0.3 (4)
N3—N2—C5—N1	172.75 (18)	C27—N8—C24—C23	−173.3 (2)
N3—N2—C5—C4	−6.9 (3)	C29—N8—C24—C23	1.7 (3)
N2—N3—C6—C11	0.5 (3)	C27—N8—C24—C25	6.9 (3)
N2—N3—C6—C7	−179.7 (2)	C29—N8—C24—C25	−178.1 (2)
N3—C6—C7—C8	−179.8 (2)	C22—C23—C24—N8	−179.0 (2)
C11—C6—C7—C8	0.0 (4)	C22—C23—C24—C25	0.8 (3)
C6—C7—C8—C9	1.1 (4)	N8—C24—C25—C26	178.6 (2)
C14—N4—C9—C8	4.7 (3)	C23—C24—C25—C26	−1.3 (3)
C12—N4—C9—C8	−165.6 (2)	C24—C25—C26—C21	1.1 (4)
C14—N4—C9—C10	−174.8 (2)	N7—C21—C26—C25	178.2 (2)
C12—N4—C9—C10	14.9 (3)	C22—C21—C26—C25	−0.5 (3)
C7—C8—C9—N4	179.8 (2)	C24—N8—C27—C28	74.3 (3)
C7—C8—C9—C10	−0.7 (3)	C29—N8—C27—C28	−101.0 (2)
N4—C9—C10—C11	178.6 (2)	C24—N8—C29—C30	−91.3 (3)
C8—C9—C10—C11	−0.9 (3)	C27—N8—C29—C30	84.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···Cl1i	0.95	2.72	3.486 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯Cl1i	0.95	2.72	3.486 (2)	138

Symmetry code: (i) .