Dichlorido{(E)-4-dimethyl-amino-N'-[(pyri-din-2-yl)methyl-idene-κN]benzo-hydrazide-κO}zinc.

In the mononuclear title complex, [ZnCl2(C15H16N4O)], the Zn(II) cation is five-coordinated in a strongly distorted square-pyramidal environment by two Cl(-) anions and a neutral tridentate Schiff base ligand. The Zn(II) cation is chelated by the carbonyl O atom, the imine N atom and the pyridine N atom, which causes a slight loss of planarity for the ligand; the dihedral angle between the aromatic rings is 4.61 (8)°.

Related literature

For related structures, see: Moreno-Fuquen et al. (2012 ▶); Chaur et al. (2011 ▶); Ma et al. (2011 ▶). For the structure of the ligand and its complex with CuCl2, see: Sangeetha, Pal & Pal (2000 ▶); Sangeetha, Pal, Anson et al. (2000 ▶). For the design of mol­ecular dynamic systems, see: Hirose (2010 ▶); Lehn (2006 ▶). For the synthetic principles of compounds exhibiting dynamic properties, see Kay et al. (2007 ▶). For information storage, see: Kandel (2001 ▶).

Experimental

Crystal data

[ZnCl2(C15H16N4O)]

M = 404.59

Monoclinic,

a = 16.1822 (7) Å

b = 13.5864 (7) Å

c = 7.5989 (2) Å

β = 91.123 (3)°

V = 1670.36 (12) Å3

Z = 4

Mo Kα radiation

μ = 1.80 mm−1

T = 173 K

0.40 × 0.22 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009 ▶) T min = 0.538, T max = 0.764

14366 measured reflections

3803 independent reflections

3252 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.084

S = 1.06

3803 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.74 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global_Publ_Block. DOI: 10.1107/S1600536812049355/bh2455sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049355/bh2455Isup2.hkl

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

[ZnCl2(C15H16N4O)]	F(000) = 824
Mr = 404.59	Dx = 1.609 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 18477 reflections
a = 16.1822 (7) Å	θ = 1.0–27.5°
b = 13.5864 (7) Å	µ = 1.80 mm−1
c = 7.5989 (2) Å	T = 173 K
β = 91.123 (3)°	Plate, orange
V = 1670.36 (12) Å3	0.40 × 0.22 × 0.10 mm
Z = 4

Nonius KappaCCD diffractometer	3803 independent reflections
Radiation source: fine-focus sealed tube	3252 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
φ and ω scans	θmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009)	h = −18→20
Tmin = 0.538, Tmax = 0.764	k = −17→16
14366 measured reflections	l = −9→8

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) = 0.084	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0401P)2 + 0.7957P] where P = (Fo2 + 2Fc2)/3
3803 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.74 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
C1	0.00605 (14)	0.89834 (18)	0.1655 (3)	0.0286 (5)
H1A	0.0063	0.9667	0.1708	0.034*
C2	−0.06416 (14)	0.85138 (19)	0.0983 (3)	0.0307 (5)
H2A	−0.1101	0.8875	0.0608	0.037*
C3	−0.06401 (14)	0.75050 (19)	0.0887 (3)	0.0291 (5)
H3A	−0.1098	0.7172	0.0428	0.035*
C4	0.00513 (13)	0.69839 (17)	0.1480 (3)	0.0241 (5)
H4A	0.0064	0.6300	0.1422	0.029*
C5	0.07173 (12)	0.75049 (16)	0.2157 (3)	0.0206 (4)
C6	0.14641 (13)	0.70244 (16)	0.2877 (3)	0.0223 (4)
H6A	0.1522	0.6344	0.2903	0.027*
C7	0.32992 (13)	0.79835 (16)	0.4744 (3)	0.0219 (4)
C8	0.40823 (13)	0.76645 (17)	0.5528 (3)	0.0226 (4)
C9	0.42999 (13)	0.66764 (18)	0.5805 (3)	0.0250 (5)
H9A	0.3925	0.6183	0.5502	0.030*
C10	0.50558 (14)	0.64279 (19)	0.6515 (3)	0.0284 (5)
H10A	0.5182	0.5768	0.6697	0.034*
C11	0.56503 (13)	0.71553 (19)	0.6978 (3)	0.0256 (5)
C12	0.54238 (14)	0.81434 (19)	0.6719 (3)	0.0282 (5)
H12A	0.5794	0.8640	0.7032	0.034*
C13	0.46628 (13)	0.83866 (18)	0.6010 (3)	0.0270 (5)
H13A	0.4530	0.9047	0.5845	0.032*
C14	0.70184 (15)	0.7651 (2)	0.8079 (3)	0.0408 (7)
H14A	0.7102	0.8067	0.7077	0.061*
H14B	0.7531	0.7341	0.8414	0.061*
H14C	0.6825	0.8040	0.9042	0.061*
C15	0.65998 (16)	0.5884 (2)	0.8059 (4)	0.0396 (6)
H15A	0.6212	0.5644	0.8897	0.059*
H15B	0.7149	0.5843	0.8552	0.059*
H15C	0.6564	0.5492	0.7009	0.059*
N1	0.07305 (11)	0.84965 (14)	0.2226 (2)	0.0232 (4)
N2	0.20292 (10)	0.76034 (14)	0.3464 (2)	0.0216 (4)
N3	0.27499 (11)	0.72631 (14)	0.4181 (2)	0.0232 (4)
H3B	0.2857	0.6645	0.4278	0.028*
N4	0.64094 (12)	0.69027 (16)	0.7633 (3)	0.0328 (5)
O1	0.31050 (10)	0.88558 (12)	0.4524 (2)	0.0295 (4)
Cl1	0.13487 (3)	1.01282 (4)	0.52926 (7)	0.02717 (13)
Cl2	0.23435 (3)	0.98562 (4)	0.07806 (7)	0.02852 (14)
Zn1	0.189086 (15)	0.914569 (19)	0.32708 (3)	0.02243 (9)

	U11	U22	U33	U12	U13	U23
C1	0.0269 (12)	0.0245 (13)	0.0343 (12)	0.0053 (9)	−0.0051 (9)	−0.0028 (9)
C2	0.0244 (12)	0.0315 (14)	0.0360 (12)	0.0074 (10)	−0.0066 (9)	−0.0026 (10)
C3	0.0229 (11)	0.0323 (14)	0.0317 (11)	−0.0025 (10)	−0.0045 (9)	−0.0051 (10)
C4	0.0247 (11)	0.0212 (12)	0.0263 (10)	−0.0005 (9)	−0.0021 (8)	−0.0015 (9)
C5	0.0212 (10)	0.0209 (11)	0.0196 (9)	−0.0010 (9)	0.0001 (8)	−0.0004 (8)
C6	0.0223 (11)	0.0193 (11)	0.0252 (10)	0.0011 (9)	−0.0027 (8)	−0.0010 (8)
C7	0.0212 (10)	0.0224 (12)	0.0221 (10)	−0.0005 (9)	0.0006 (8)	−0.0015 (8)
C8	0.0179 (10)	0.0283 (12)	0.0216 (10)	0.0019 (9)	0.0004 (8)	−0.0007 (9)
C9	0.0214 (11)	0.0264 (12)	0.0271 (10)	−0.0007 (9)	−0.0012 (8)	0.0005 (9)
C10	0.0245 (12)	0.0259 (13)	0.0345 (12)	0.0054 (9)	−0.0036 (9)	0.0031 (10)
C11	0.0181 (10)	0.0376 (14)	0.0210 (10)	0.0018 (10)	−0.0001 (8)	0.0021 (9)
C12	0.0218 (11)	0.0338 (13)	0.0290 (11)	−0.0046 (10)	−0.0028 (9)	0.0015 (10)
C13	0.0237 (11)	0.0275 (13)	0.0297 (11)	0.0023 (10)	−0.0024 (9)	0.0032 (9)
C14	0.0225 (12)	0.061 (2)	0.0390 (14)	−0.0028 (12)	−0.0078 (10)	0.0057 (13)
C15	0.0289 (13)	0.0446 (17)	0.0448 (14)	0.0154 (12)	−0.0089 (11)	−0.0008 (12)
N1	0.0226 (9)	0.0215 (10)	0.0252 (9)	−0.0005 (8)	−0.0012 (7)	0.0009 (7)
N2	0.0184 (9)	0.0235 (10)	0.0228 (8)	0.0015 (7)	−0.0003 (7)	0.0018 (7)
N3	0.0183 (9)	0.0211 (10)	0.0299 (9)	0.0039 (8)	−0.0050 (7)	0.0009 (7)
N4	0.0207 (10)	0.0404 (13)	0.0371 (10)	0.0009 (9)	−0.0056 (8)	0.0058 (9)
O1	0.0233 (8)	0.0224 (9)	0.0424 (9)	0.0016 (7)	−0.0081 (7)	0.0008 (7)
Cl1	0.0256 (3)	0.0239 (3)	0.0319 (3)	0.0018 (2)	−0.0017 (2)	−0.0059 (2)
Cl2	0.0302 (3)	0.0234 (3)	0.0321 (3)	0.0013 (2)	0.0022 (2)	0.0035 (2)
Zn1	0.02174 (15)	0.01823 (15)	0.02718 (15)	0.00072 (10)	−0.00272 (10)	−0.00081 (9)

C1—N1	1.335 (3)	C10—H10A	0.9300
C1—C2	1.391 (3)	C11—N4	1.360 (3)
C1—H1A	0.9300	C11—C12	1.404 (3)
C2—C3	1.373 (4)	C12—C13	1.375 (3)
C2—H2A	0.9300	C12—H12A	0.9300
C3—C4	1.392 (3)	C13—H13A	0.9300
C3—H3A	0.9300	C14—N4	1.452 (3)
C4—C5	1.380 (3)	C14—H14A	0.9600
C4—H4A	0.9300	C14—H14B	0.9600
C5—N1	1.348 (3)	C14—H14C	0.9600
C5—C6	1.470 (3)	C15—N4	1.453 (3)
C6—N2	1.280 (3)	C15—H15A	0.9600
C6—H6A	0.9300	C15—H15B	0.9600
C7—O1	1.237 (3)	C15—H15C	0.9600
C7—N3	1.384 (3)	N1—Zn1	2.2080 (18)
C7—C8	1.456 (3)	N2—N3	1.358 (2)
C8—C13	1.402 (3)	N2—Zn1	2.1122 (19)
C8—C9	1.403 (3)	N3—H3B	0.8600
C9—C10	1.369 (3)	O1—Zn1	2.2019 (15)
C9—H9A	0.9300	Cl1—Zn1	2.2282 (6)
C10—C11	1.419 (3)	Cl2—Zn1	2.2590 (6)
N1—C1—C2	123.0 (2)	C12—C13—H13A	119.2
N1—C1—H1A	118.5	C8—C13—H13A	119.2
C2—C1—H1A	118.5	N4—C14—H14A	109.5
C3—C2—C1	118.4 (2)	N4—C14—H14B	109.5
C3—C2—H2A	120.8	H14A—C14—H14B	109.5
C1—C2—H2A	120.8	N4—C14—H14C	109.5
C2—C3—C4	119.5 (2)	H14A—C14—H14C	109.5
C2—C3—H3A	120.2	H14B—C14—H14C	109.5
C4—C3—H3A	120.2	N4—C15—H15A	109.5
C5—C4—C3	118.5 (2)	N4—C15—H15B	109.5
C5—C4—H4A	120.8	H15A—C15—H15B	109.5
C3—C4—H4A	120.8	N4—C15—H15C	109.5
N1—C5—C4	122.6 (2)	H15A—C15—H15C	109.5
N1—C5—C6	114.65 (18)	H15B—C15—H15C	109.5
C4—C5—C6	122.8 (2)	C1—N1—C5	118.04 (19)
N2—C6—C5	115.7 (2)	C1—N1—Zn1	126.75 (16)
N2—C6—H6A	122.2	C5—N1—Zn1	115.20 (14)
C5—C6—H6A	122.2	C6—N2—N3	122.18 (19)
O1—C7—N3	118.41 (19)	C6—N2—Zn1	120.75 (15)
O1—C7—C8	123.9 (2)	N3—N2—Zn1	117.03 (14)
N3—C7—C8	117.7 (2)	N2—N3—C7	115.11 (18)
C13—C8—C9	117.7 (2)	N2—N3—H3B	122.4
C13—C8—C7	118.2 (2)	C7—N3—H3B	122.4
C9—C8—C7	124.1 (2)	C11—N4—C14	120.9 (2)
C10—C9—C8	121.0 (2)	C11—N4—C15	120.5 (2)
C10—C9—H9A	119.5	C14—N4—C15	118.4 (2)
C8—C9—H9A	119.5	C7—O1—Zn1	116.88 (14)
C9—C10—C11	121.5 (2)	N2—Zn1—O1	72.54 (6)
C9—C10—H10A	119.3	N2—Zn1—N1	73.56 (7)
C11—C10—H10A	119.3	O1—Zn1—N1	146.03 (7)
N4—C11—C12	121.6 (2)	N2—Zn1—Cl1	126.09 (5)
N4—C11—C10	121.2 (2)	O1—Zn1—Cl1	99.73 (5)
C12—C11—C10	117.2 (2)	N1—Zn1—Cl1	98.25 (5)
C13—C12—C11	120.9 (2)	N2—Zn1—Cl2	116.52 (5)
C13—C12—H12A	119.5	O1—Zn1—Cl2	97.90 (5)
C11—C12—H12A	119.5	N1—Zn1—Cl2	99.04 (5)
C12—C13—C8	121.6 (2)	Cl1—Zn1—Cl2	117.39 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···Cl2i	0.86	2.49	3.199 (2)	140