Literature DB >> 21579066

Dichlorido[N-(2-pyridylmethyl-idene)benzene-1,4-diamine]zinc(II).

Yun-Fen Shi, Qiao-Hua Feng, Wen-Jie Zhao, Yun-Bo Shi, Peng Zhan.

Abstract

In the title compound, [ZnCl(2)(C(12)H(11)N(3))], the Zn(II) atom is four-coordinated by two N atoms from an N-(2-pyridylmethyl-ene)benzene-1,4-diamine ligand and two Cl atoms in a distorted tetra-hedral geometry. In the crystal, the complex mol-ecules are connected by N-H⋯Cl and C-H⋯Cl hydrogen bonds into a two-dimensional layer structure parallel to (110).

Entities: Chemical Disease Species

Year: 2010 PMID： 21579066 PMCID： PMC2979197 DOI： 10.1107/S1600536810015138

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For general background to zinc(II) complexes with Schiff base ligands, see: Su et al. (1999 ▶); Ye et al. (2005 ▶).

Experimental

Crystal data

[ZnCl2(C12H11N3)] M = 333.53 Triclinic, a = 7.5004 (15) Å b = 9.1168 (18) Å c = 10.186 (2) Å α = 84.36 (3)° β = 82.27 (3)° γ = 74.19 (3)° V = 662.7 (3) Å3 Z = 2 Mo Kα radiation μ = 2.24 mm−1 T = 293 K 0.20 × 0.18 × 0.16 mm

Data collection

Rigaku R-AXIS RAPID diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.645, T max = 0.699 6557 measured reflections 3000 independent reflections 2345 reflections with I > 2σ(I) R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.108 S = 0.93 3000 reflections 175 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.39 e Å−3 Δρmin = −0.37 e Å−3 Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810015138/hy2300sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015138/hy2300Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[ZnCl₂(C₁₂H₁₁N₃)]	Z = 2
M_r = 333.53	F(000) = 336
Triclinic, P1	D_x = 1.671 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5004 (15) Å	Cell parameters from 2613 reflections
b = 9.1168 (18) Å	θ = 3.2–26.5°
c = 10.186 (2) Å	µ = 2.24 mm⁻¹
α = 84.36 (3)°	T = 293 K
β = 82.27 (3)°	Block, red
γ = 74.19 (3)°	0.20 × 0.18 × 0.16 mm
V = 662.7 (3) Å³

Rigaku R-AXIS RAPID diffractometer	3000 independent reflections
Radiation source: fine-focus sealed tube	2345 reflections with I > 2σ(I)
graphite	R_int = 0.027
ω scans	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
T_min = 0.645, T_max = 0.699	k = −11→11
6557 measured reflections	l = −13→13

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ²(F_o²) + (0.058P)² + 0.9028P] where P = (F_o² + 2F_c²)/3
3000 reflections	(Δ/σ)_max < 0.001
175 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

	x	y	z	U_iso*/U_eq
Zn1	0.27968 (6)	0.38462 (4)	0.24431 (4)	0.03673 (14)
Cl2	0.09004 (13)	0.22915 (11)	0.26242 (10)	0.0490 (2)
Cl4	0.55281 (14)	0.29132 (12)	0.13201 (10)	0.0515 (3)
N4	0.1317 (4)	0.6067 (3)	0.2044 (3)	0.0353 (6)
N6	0.2715 (4)	0.4658 (3)	0.4284 (3)	0.0308 (6)
C2	−0.0484 (6)	0.8248 (5)	0.0885 (4)	0.0492 (9)
H2	−0.0941	0.8704	0.0098	0.059*
C3	−0.0912 (6)	0.9047 (5)	0.2008 (4)	0.0508 (10)
C4	−0.0201 (6)	0.8340 (4)	0.3174 (4)	0.0455 (9)
C1	0.0631 (5)	0.6763 (4)	0.0925 (4)	0.0433 (8)
H1	0.0912	0.6232	0.0157	0.052*
C11	0.5458 (6)	0.1380 (4)	0.6210 (4)	0.0422 (8)
N11	0.5896 (5)	0.0970 (4)	0.8533 (3)	0.0536 (9)
H11	0.6555	0.0052	0.8408	0.064*
H10	0.5698	0.1306	0.9314	0.064*
C9	0.4073 (5)	0.3393 (4)	0.7684 (3)	0.0375 (7)
H8	0.3895	0.3764	0.8524	0.045*
C5	0.0910 (5)	0.6854 (4)	0.3156 (3)	0.0342 (7)
C10	0.5160 (5)	0.1897 (4)	0.7488 (3)	0.0366 (7)
C6	0.1730 (5)	0.6044 (4)	0.4344 (3)	0.0357 (7)
H6	0.1536	0.6533	0.5131	0.043*
C8	0.3268 (5)	0.4319 (4)	0.6659 (3)	0.0347 (7)
H7	0.2548	0.5306	0.6812	0.042*
C12	0.4640 (5)	0.2327 (4)	0.5178 (3)	0.0382 (8)
H9	0.4845	0.1973	0.4330	0.046*
C7	0.3523 (4)	0.3789 (4)	0.5390 (3)	0.0312 (7)
H5	0.604 (6)	0.045 (5)	0.601 (4)	0.050 (12)*
H4	−0.030 (7)	0.890 (6)	0.403 (5)	0.070 (14)*
H3	−0.189 (7)	1.002 (6)	0.196 (5)	0.079 (16)*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0404 (2)	0.0338 (2)	0.0327 (2)	−0.00136 (17)	−0.00508 (16)	−0.00900 (15)
Cl2	0.0465 (5)	0.0419 (5)	0.0599 (6)	−0.0092 (4)	−0.0042 (4)	−0.0183 (4)
Cl4	0.0469 (5)	0.0540 (5)	0.0475 (5)	−0.0026 (4)	0.0052 (4)	−0.0188 (4)
N4	0.0341 (15)	0.0352 (15)	0.0347 (14)	−0.0062 (12)	−0.0034 (12)	−0.0027 (12)
N6	0.0322 (14)	0.0299 (13)	0.0291 (13)	−0.0059 (11)	−0.0029 (11)	−0.0030 (10)
C2	0.051 (2)	0.047 (2)	0.049 (2)	−0.0123 (18)	−0.0147 (18)	0.0131 (18)
C3	0.045 (2)	0.038 (2)	0.063 (3)	0.0000 (17)	−0.0106 (19)	0.0056 (18)
C4	0.049 (2)	0.0335 (18)	0.052 (2)	−0.0061 (16)	−0.0058 (18)	−0.0070 (16)
C1	0.042 (2)	0.048 (2)	0.0377 (18)	−0.0097 (16)	−0.0052 (15)	0.0034 (16)
C11	0.054 (2)	0.0295 (17)	0.0401 (19)	−0.0002 (16)	−0.0105 (16)	−0.0089 (15)
N11	0.077 (3)	0.0386 (17)	0.0373 (16)	0.0017 (16)	−0.0176 (16)	0.0005 (13)
C9	0.043 (2)	0.0383 (18)	0.0299 (16)	−0.0080 (15)	−0.0015 (14)	−0.0092 (14)
C5	0.0333 (17)	0.0323 (16)	0.0369 (17)	−0.0084 (14)	−0.0036 (14)	−0.0024 (13)
C10	0.0409 (19)	0.0344 (17)	0.0348 (17)	−0.0098 (15)	−0.0049 (14)	−0.0029 (14)
C6	0.0389 (19)	0.0352 (17)	0.0327 (16)	−0.0079 (14)	−0.0017 (14)	−0.0089 (13)
C8	0.0386 (18)	0.0311 (16)	0.0334 (16)	−0.0067 (14)	−0.0006 (14)	−0.0085 (13)
C12	0.045 (2)	0.0345 (17)	0.0333 (16)	−0.0035 (15)	−0.0057 (14)	−0.0109 (14)
C7	0.0309 (16)	0.0320 (16)	0.0314 (15)	−0.0084 (13)	−0.0054 (13)	−0.0026 (12)

Zn1—N4	2.057 (3)	C11—C12	1.391 (5)
Zn1—N6	2.070 (3)	C11—C10	1.396 (5)
Zn1—Cl4	2.2000 (13)	C11—H5	0.87 (4)
Zn1—Cl2	2.2456 (12)	N11—C10	1.371 (4)
N4—C1	1.343 (4)	N11—H11	0.8600
N4—C5	1.356 (4)	N11—H10	0.8600
N6—C6	1.281 (4)	C9—C8	1.374 (5)
N6—C7	1.418 (4)	C9—C10	1.403 (5)
C2—C3	1.370 (6)	C9—H8	0.9300
C2—C1	1.384 (5)	C5—C6	1.472 (5)
C2—H2	0.9300	C6—H6	0.9300
C3—C4	1.394 (6)	C8—C7	1.395 (4)
C3—H3	0.99 (5)	C8—H7	0.9300
C4—C5	1.384 (5)	C12—C7	1.387 (5)
C4—H4	1.03 (5)	C12—H9	0.9300
C1—H1	0.9300

N4—Zn1—N6	81.72 (11)	C10—C11—H5	125 (3)
N4—Zn1—Cl4	120.24 (9)	C10—N11—H11	120.0
N6—Zn1—Cl4	118.70 (9)	C10—N11—H10	120.0
N4—Zn1—Cl2	109.98 (9)	H11—N11—H10	120.0
N6—Zn1—Cl2	108.64 (8)	C8—C9—C10	121.2 (3)
Cl4—Zn1—Cl2	113.46 (4)	C8—C9—H8	119.4
C1—N4—C5	118.7 (3)	C10—C9—H8	119.4
C1—N4—Zn1	130.3 (3)	N4—C5—C4	122.1 (3)
C5—N4—Zn1	110.8 (2)	N4—C5—C6	116.2 (3)
C6—N6—C7	122.8 (3)	C4—C5—C6	121.7 (3)
C6—N6—Zn1	111.6 (2)	N11—C10—C11	121.2 (3)
C7—N6—Zn1	125.5 (2)	N11—C10—C9	120.4 (3)
C3—C2—C1	119.9 (4)	C11—C10—C9	118.4 (3)
C3—C2—H2	120.0	N6—C6—C5	119.3 (3)
C1—C2—H2	120.0	N6—C6—H6	120.3
C2—C3—C4	118.9 (4)	C5—C6—H6	120.3
C2—C3—H3	116 (3)	C9—C8—C7	120.4 (3)
C4—C3—H3	124 (3)	C9—C8—H7	119.8
C5—C4—C3	118.7 (4)	C7—C8—H7	119.8
C5—C4—H4	117 (3)	C7—C12—C11	121.2 (3)
C3—C4—H4	124 (3)	C7—C12—H9	119.4
N4—C1—C2	121.7 (4)	C11—C12—H9	119.4
N4—C1—H1	119.1	C12—C7—C8	118.8 (3)
C2—C1—H1	119.1	C12—C7—N6	117.2 (3)
C12—C11—C10	120.0 (3)	C8—C7—N6	124.0 (3)
C12—C11—H5	115 (3)

N6—Zn1—N4—C1	179.7 (3)	C3—C4—C5—N4	−0.4 (6)
Cl4—Zn1—N4—C1	61.3 (3)	C3—C4—C5—C6	179.1 (3)
Cl2—Zn1—N4—C1	−73.4 (3)	C12—C11—C10—N11	177.7 (4)
N6—Zn1—N4—C5	−5.4 (2)	C12—C11—C10—C9	−1.9 (6)
Cl4—Zn1—N4—C5	−123.9 (2)	C8—C9—C10—N11	−177.6 (3)
Cl2—Zn1—N4—C5	101.5 (2)	C8—C9—C10—C11	2.0 (5)
N4—Zn1—N6—C6	4.4 (2)	C7—N6—C6—C5	−178.8 (3)
Cl4—Zn1—N6—C6	124.4 (2)	Zn1—N6—C6—C5	−2.7 (4)
Cl2—Zn1—N6—C6	−104.0 (2)	N4—C5—C6—N6	−2.0 (5)
N4—Zn1—N6—C7	−179.7 (3)	C4—C5—C6—N6	178.4 (3)
Cl4—Zn1—N6—C7	−59.6 (3)	C10—C9—C8—C7	−0.3 (5)
Cl2—Zn1—N6—C7	72.0 (3)	C10—C11—C12—C7	0.1 (6)
C1—C2—C3—C4	0.3 (6)	C11—C12—C7—C8	1.7 (5)
C2—C3—C4—C5	−0.1 (6)	C11—C12—C7—N6	−178.6 (3)
C5—N4—C1—C2	−0.5 (5)	C9—C8—C7—C12	−1.6 (5)
Zn1—N4—C1—C2	174.1 (3)	C9—C8—C7—N6	178.8 (3)
C3—C2—C1—N4	0.0 (6)	C6—N6—C7—C12	−176.7 (3)
C1—N4—C5—C4	0.7 (5)	Zn1—N6—C7—C12	7.8 (4)
Zn1—N4—C5—C4	−174.9 (3)	C6—N6—C7—C8	3.0 (5)
C1—N4—C5—C6	−178.8 (3)	Zn1—N6—C7—C8	−172.5 (2)
Zn1—N4—C5—C6	5.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H10···Cl4ⁱ	0.86	2.60	3.433 (4)	164
N11—H11···Cl2ⁱⁱ	0.86	2.64	3.470 (4)	161
C3—H3···Cl4ⁱⁱⁱ	0.99 (5)	2.89 (5)	3.864 (4)	169 (4)
C6—H6···Cl2^iv	0.93	2.83	3.658 (4)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H10⋯Cl4ⁱ	0.86	2.60	3.433 (4)	164
N11—H11⋯Cl2ⁱⁱ	0.86	2.64	3.470 (4)	161
C3—H3⋯Cl4ⁱⁱⁱ	0.99 (5)	2.89 (5)	3.864 (4)	169 (4)
C6—H6⋯Cl2^iv	0.93	2.83	3.658 (4)	149

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

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Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

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