Dichlorido{N,N-dimethyl-N′-[1-(2-pyrid­yl)ethyl­idene]ethane-1,2-diamine-κ3N,N′,N′′}zinc

Suleiman Gwaram, N.; Khaledi, H.; Mohd Ali, H.

doi:10.1107/S1600536811025669

Dichlorido{N,N-dimethyl-N′-[1-(2-pyridyl)ethylidene]ethane-1,2-diamine-κ³N,N′,N′′}zinc

N. Suleiman Gwaram, H. Khaledi and H. Mohd Ali

The asymmetric unit of the title compound, [ZnCl₂(C₁₁H₁₇N₃)], contains two independent pentacoordinate Zn^II complex molecules. In each molecule, the metal atom is coordinated by an N,N′,N′′-tridenate Schiff base and two Cl atoms in a distorted square-pyramidal geometry. The two molecules differ little in their geometry, but more in their intermolecular interactions. In the crystal, adjacent molecules are connected via C—H

Cl interactions into a three-dimensional supramolecular structure. The network is supplemented by π–π interactions formed between the aromatic rings of pairs of the symmetry-related molecules [centroid–centroid distances = 3.6255 (10) and 3.7073 (10) Å]. The crystal lattice contains void spaces with a size of 52 Å³.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811025669/om2444sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536811025669/om2444Isup2.hkl Contains datablock I

CCDC reference: 840996

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.021
wR factor = 0.052
Data-to-parameter ratio = 20.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .         52 A   3 
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         12
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600          2

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   1 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

The crystal structure of the title Zn^II complex is isomorphous with that of the Mn^II analogue (Ikmal Hisham et al., 2011). The asymmetric unit consists of two geometrically slightly different molecules; the weighted r.m.s. fit for the superposition of the non-H atoms in both molecules (after inversion) being 0.078 Å. The metal centers are five-coordinate in distorted square-pyramidal geometries, the apical positions being occupied by a chlorine atom. The Addison τ values (Addison et al., 1984) for Zn1 and Zn2 molecules are 0.103 and 0.168, respectively. The Zn—Cl and Zn—N bond lengths are comparable to those reported for similar complexes (Gourbatsis et al., 1999, Sun, 2005). In the crystal, the molecules are linked through C—H···Cl interactions (Table 1) into a three-dimensional polymeric structure and this is consolidated by π–π interactions formed between pairs of molecules [Cg1···Cg1ⁱ = 3.6255 (10) Å; Cg2···Cg2ⁱⁱ = 3.7073 (10) Å, where Cg1 and Cg2, are the centroids of the rings N1/C1—C5 and N4/C12—C16, for i: -x, -y + 1, -z; ii: -x + 1, -y + 1, -z + 1]. The lattice contains void spaces with the size of 52 Å³ within which there is no evidence for included solvent.

Related literature top

For the isotypic Mn(II) complex, see: Ikmal Hisham et al. (2011). For the crystal structures of similar ZnCl₂ complexes, see: Gourbatsis et al. (1999); Sun (2005). For a description of the geometry of five-coordinate metal complexes, see: Addison et al. (1984).

Experimental top

A mixture of 2-acetylpyridine (0.20 g, 1.65 mmol) and N,N-dimethylethyldiamine (0.15 g, 1.65 mmol) in ethanol (20 ml) was refluxed for 2 hr followed by addition of a solution of zinc(II) chloride (0.225 g, 1.65 mmol) in the minimum amount of water. The resulting solution was refluxed for 30 min, and then set aside at room temperature. The colorless crystals of the title compound were obtained in a few days.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Dichlorido{N,N-dimethyl-N'-[1-(2- pyridyl)ethylidene]ethane-1,2-diamine- κ³N,N',N''}zinc top

Crystal data top

[ZnCl₂(C₁₁H₁₇N₃)]	F(000) = 1344
M_r = 327.55	D_x = 1.507 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9925 reflections
a = 17.4849 (8) Å	θ = 2.4–30.6°
b = 9.8161 (4) Å	µ = 2.05 mm⁻¹
c = 20.4264 (7) Å	T = 100 K
β = 124.578 (3)°	Block, colorless
V = 2886.6 (2) Å³	0.27 × 0.23 × 0.15 mm
Z = 8

Data collection top

Bruker APEXII CCD diffractometer	6294 independent reflections
Radiation source: fine-focus sealed tube	5510 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 27.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→21
T_min = 0.607, T_max = 0.748	k = −12→12
20477 measured reflections	l = −26→26

Refinement top

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.052	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0226P)² + 0.9433P] where P = (F_o² + 2F_c²)/3
6294 reflections	(Δ/σ)_max = 0.002
313 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

[ZnCl₂(C₁₁H₁₇N₃)]	V = 2886.6 (2) Å³
M_r = 327.55	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.4849 (8) Å	µ = 2.05 mm⁻¹
b = 9.8161 (4) Å	T = 100 K
c = 20.4264 (7) Å	0.27 × 0.23 × 0.15 mm
β = 124.578 (3)°

Data collection top

Bruker APEXII CCD diffractometer	6294 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5510 reflections with I > 2σ(I)
T_min = 0.607, T_max = 0.748	R_int = 0.022
20477 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	0 restraints
wR(F²) = 0.052	H-atom parameters constrained
S = 1.04	Δρ_max = 0.36 e Å⁻³
6294 reflections	Δρ_min = −0.28 e Å⁻³
313 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.097383 (12)	0.523307 (18)	0.248455 (10)	0.01180 (5)
Cl1	0.22099 (3)	0.66993 (4)	0.31121 (2)	0.01561 (8)
Cl2	0.14396 (3)	0.31088 (4)	0.23943 (2)	0.01519 (8)
N1	0.03628 (9)	0.60104 (13)	0.12863 (8)	0.0139 (3)
N2	−0.04898 (9)	0.51386 (13)	0.19110 (8)	0.0141 (3)
N3	0.08663 (9)	0.49253 (13)	0.34845 (8)	0.0141 (3)
C1	0.08312 (12)	0.65350 (16)	0.10080 (10)	0.0181 (3)
H1	0.1487	0.6620	0.1358	0.022*
C2	0.03935 (13)	0.69606 (17)	0.02250 (10)	0.0225 (4)
H2	0.0745	0.7317	0.0041	0.027*
C3	−0.05605 (13)	0.68571 (18)	−0.02813 (10)	0.0238 (4)
H3	−0.0876	0.7140	−0.0820	0.029*
C4	−0.10510 (12)	0.63350 (17)	0.00065 (10)	0.0202 (3)
H4	−0.1709	0.6268	−0.0330	0.024*
C5	−0.05711 (11)	0.59111 (16)	0.07919 (9)	0.0156 (3)
C6	−0.10354 (11)	0.53702 (15)	0.11671 (10)	0.0153 (3)
C7	−0.20671 (12)	0.51654 (19)	0.06620 (11)	0.0247 (4)
H7A	−0.2272	0.4868	0.0997	0.037*
H7B	−0.2229	0.4469	0.0259	0.037*
H7C	−0.2375	0.6025	0.0400	0.037*
C8	−0.08002 (11)	0.46662 (16)	0.24024 (10)	0.0161 (3)
H8A	−0.1292	0.3968	0.2113	0.019*
H8B	−0.1056	0.5436	0.2534	0.019*
C9	0.00363 (11)	0.40623 (16)	0.31586 (9)	0.0167 (3)
H9A	−0.0107	0.3962	0.3560	0.020*
H9B	0.0166	0.3145	0.3043	0.020*
C10	0.16872 (11)	0.42164 (17)	0.41521 (9)	0.0196 (3)
H10A	0.2242	0.4774	0.4349	0.029*
H10B	0.1762	0.3336	0.3969	0.029*
H10C	0.1601	0.4069	0.4581	0.029*
C11	0.07513 (12)	0.62345 (17)	0.37716 (10)	0.0186 (3)
H11A	0.0239	0.6745	0.3324	0.028*
H11B	0.1326	0.6765	0.4015	0.028*
H11C	0.0613	0.6065	0.4167	0.028*
Zn2	0.381351 (12)	0.529056 (18)	0.644032 (11)	0.01293 (5)
Cl3	0.34646 (3)	0.30943 (4)	0.59819 (2)	0.01758 (8)
Cl4	0.27052 (3)	0.69499 (4)	0.58273 (2)	0.01882 (9)
N4	0.45804 (9)	0.59876 (13)	0.59532 (8)	0.0145 (3)
N5	0.52234 (9)	0.51339 (13)	0.73866 (8)	0.0130 (3)
N6	0.37431 (9)	0.51154 (13)	0.74869 (8)	0.0163 (3)
C12	0.42130 (12)	0.64614 (16)	0.52195 (10)	0.0182 (3)
H12	0.3558	0.6565	0.4872	0.022*
C13	0.47570 (12)	0.68075 (17)	0.49470 (10)	0.0205 (4)
H13	0.4477	0.7133	0.4420	0.025*
C14	0.57101 (12)	0.66722 (16)	0.54521 (10)	0.0198 (4)
H14	0.6095	0.6906	0.5279	0.024*
C15	0.60962 (11)	0.61874 (16)	0.62199 (10)	0.0161 (3)
H15	0.6750	0.6085	0.6580	0.019*
C16	0.55100 (11)	0.58562 (15)	0.64499 (9)	0.0130 (3)
C17	0.58544 (11)	0.53679 (15)	0.72681 (9)	0.0129 (3)
C18	0.68712 (11)	0.52205 (17)	0.78736 (10)	0.0181 (3)
H18A	0.7152	0.6124	0.8059	0.027*
H18B	0.7153	0.4753	0.7636	0.027*
H18C	0.6978	0.4688	0.8324	0.027*
C19	0.54256 (11)	0.46863 (16)	0.81533 (9)	0.0157 (3)
H19A	0.5678	0.5453	0.8536	0.019*
H19B	0.5891	0.3943	0.8374	0.019*
C20	0.45215 (11)	0.41849 (16)	0.80131 (10)	0.0172 (3)
H20A	0.4377	0.3267	0.7770	0.021*
H20B	0.4595	0.4110	0.8529	0.021*
C21	0.38747 (13)	0.64417 (17)	0.78738 (11)	0.0234 (4)
H21A	0.3349	0.7038	0.7516	0.035*
H21B	0.4451	0.6861	0.7997	0.035*
H21C	0.3912	0.6309	0.8367	0.035*
C22	0.28596 (12)	0.4513 (2)	0.72779 (11)	0.0263 (4)
H22A	0.2878	0.4376	0.7762	0.039*
H22B	0.2766	0.3634	0.7015	0.039*
H22C	0.2346	0.5127	0.6918	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.01005 (10)	0.01180 (9)	0.01230 (9)	0.00035 (7)	0.00560 (8)	0.00060 (7)
Cl1	0.01217 (18)	0.01420 (18)	0.01770 (19)	−0.00150 (14)	0.00683 (16)	−0.00033 (14)
Cl2	0.01386 (19)	0.01249 (18)	0.01870 (19)	0.00000 (14)	0.00892 (16)	−0.00121 (14)
N1	0.0130 (7)	0.0136 (7)	0.0141 (6)	0.0031 (5)	0.0071 (6)	0.0012 (5)
N2	0.0132 (7)	0.0117 (6)	0.0175 (7)	0.0005 (5)	0.0088 (6)	−0.0004 (5)
N3	0.0128 (7)	0.0131 (6)	0.0142 (7)	0.0005 (5)	0.0064 (6)	0.0003 (5)
C1	0.0182 (9)	0.0167 (8)	0.0211 (8)	0.0044 (7)	0.0122 (7)	0.0029 (6)
C2	0.0274 (10)	0.0221 (9)	0.0227 (9)	0.0062 (7)	0.0170 (8)	0.0067 (7)
C3	0.0294 (10)	0.0232 (9)	0.0151 (8)	0.0067 (7)	0.0105 (8)	0.0033 (7)
C4	0.0188 (9)	0.0201 (9)	0.0158 (8)	0.0025 (7)	0.0062 (7)	−0.0008 (7)
C5	0.0161 (8)	0.0121 (8)	0.0153 (8)	0.0018 (6)	0.0068 (7)	−0.0023 (6)
C6	0.0137 (8)	0.0114 (7)	0.0179 (8)	0.0003 (6)	0.0072 (7)	−0.0017 (6)
C7	0.0150 (9)	0.0282 (10)	0.0222 (9)	−0.0020 (7)	0.0055 (8)	0.0009 (7)
C8	0.0147 (8)	0.0158 (8)	0.0198 (8)	−0.0029 (6)	0.0109 (7)	−0.0009 (6)
C9	0.0182 (9)	0.0144 (8)	0.0197 (8)	−0.0015 (6)	0.0120 (7)	0.0009 (6)
C10	0.0179 (9)	0.0203 (9)	0.0166 (8)	0.0038 (7)	0.0074 (7)	0.0048 (7)
C11	0.0186 (9)	0.0178 (8)	0.0189 (8)	0.0017 (7)	0.0103 (7)	−0.0035 (7)
Zn2	0.01031 (10)	0.01210 (9)	0.01425 (9)	−0.00008 (7)	0.00570 (8)	−0.00033 (7)
Cl3	0.0177 (2)	0.01292 (18)	0.01780 (19)	−0.00023 (15)	0.00746 (17)	−0.00134 (14)
Cl4	0.0140 (2)	0.01604 (19)	0.02074 (19)	0.00305 (15)	0.00643 (17)	0.00000 (15)
N4	0.0132 (7)	0.0133 (7)	0.0142 (7)	−0.0006 (5)	0.0062 (6)	−0.0007 (5)
N5	0.0126 (7)	0.0121 (6)	0.0138 (6)	0.0007 (5)	0.0071 (6)	0.0003 (5)
N6	0.0143 (7)	0.0154 (7)	0.0205 (7)	−0.0009 (5)	0.0107 (6)	−0.0018 (5)
C12	0.0157 (8)	0.0182 (8)	0.0147 (8)	0.0000 (7)	0.0051 (7)	0.0007 (6)
C13	0.0264 (10)	0.0181 (8)	0.0165 (8)	−0.0003 (7)	0.0118 (8)	0.0021 (6)
C14	0.0253 (9)	0.0179 (8)	0.0221 (9)	−0.0022 (7)	0.0168 (8)	0.0005 (7)
C15	0.0144 (8)	0.0151 (8)	0.0190 (8)	0.0005 (6)	0.0096 (7)	−0.0011 (6)
C16	0.0127 (8)	0.0102 (7)	0.0138 (7)	0.0012 (6)	0.0062 (7)	−0.0009 (6)
C17	0.0117 (8)	0.0097 (7)	0.0142 (8)	−0.0005 (6)	0.0055 (7)	−0.0021 (6)
C18	0.0124 (8)	0.0215 (9)	0.0184 (8)	0.0004 (7)	0.0075 (7)	0.0017 (7)
C19	0.0169 (8)	0.0165 (8)	0.0145 (8)	0.0020 (6)	0.0093 (7)	0.0027 (6)
C20	0.0196 (9)	0.0155 (8)	0.0177 (8)	0.0008 (7)	0.0113 (7)	0.0017 (6)
C21	0.0255 (10)	0.0216 (9)	0.0248 (9)	0.0036 (7)	0.0152 (8)	−0.0044 (7)
C22	0.0199 (10)	0.0327 (10)	0.0310 (10)	−0.0051 (8)	0.0173 (9)	−0.0013 (8)

Geometric parameters (Å, º) top

Zn1—N2	2.1278 (13)	Zn2—N5	2.1044 (13)
Zn1—N3	2.1758 (13)	Zn2—N4	2.1842 (13)
Zn1—N1	2.1785 (13)	Zn2—N6	2.2166 (13)
Zn1—Cl2	2.2837 (4)	Zn2—Cl4	2.2852 (4)
Zn1—Cl1	2.2893 (4)	Zn2—Cl3	2.2910 (4)
N1—C1	1.337 (2)	N4—C12	1.335 (2)
N1—C5	1.351 (2)	N4—C16	1.348 (2)
N2—C6	1.275 (2)	N5—C17	1.2775 (19)
N2—C8	1.4612 (19)	N5—C19	1.4635 (19)
N3—C11	1.473 (2)	N6—C21	1.472 (2)
N3—C9	1.473 (2)	N6—C22	1.473 (2)
N3—C10	1.477 (2)	N6—C20	1.477 (2)
C1—C2	1.389 (2)	C12—C13	1.390 (2)
C1—H1	0.9500	C12—H12	0.9500
C2—C3	1.380 (3)	C13—C14	1.381 (2)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.384 (2)	C14—C15	1.393 (2)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.387 (2)	C15—C16	1.387 (2)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.495 (2)	C16—C17	1.498 (2)
C6—C7	1.499 (2)	C17—C18	1.488 (2)
C7—H7A	0.9800	C18—H18A	0.9800
C7—H7B	0.9800	C18—H18B	0.9800
C7—H7C	0.9800	C18—H18C	0.9800
C8—C9	1.521 (2)	C19—C20	1.520 (2)
C8—H8A	0.9900	C19—H19A	0.9900
C8—H8B	0.9900	C19—H19B	0.9900
C9—H9A	0.9900	C20—H20A	0.9900
C9—H9B	0.9900	C20—H20B	0.9900
C10—H10A	0.9800	C21—H21A	0.9800
C10—H10B	0.9800	C21—H21B	0.9800
C10—H10C	0.9800	C21—H21C	0.9800
C11—H11A	0.9800	C22—H22A	0.9800
C11—H11B	0.9800	C22—H22B	0.9800
C11—H11C	0.9800	C22—H22C	0.9800

N2—Zn1—N3	78.06 (5)	N5—Zn2—N4	74.89 (5)
N2—Zn1—N1	74.15 (5)	N5—Zn2—N6	77.63 (5)
N3—Zn1—N1	148.73 (5)	N4—Zn2—N6	148.01 (5)
N2—Zn1—Cl2	106.76 (4)	N5—Zn2—Cl4	137.94 (4)
N3—Zn1—Cl2	100.01 (4)	N4—Zn2—Cl4	94.36 (4)
N1—Zn1—Cl2	101.48 (3)	N6—Zn2—Cl4	95.15 (4)
N2—Zn1—Cl1	142.56 (4)	N5—Zn2—Cl3	102.01 (4)
N3—Zn1—Cl1	96.82 (4)	N4—Zn2—Cl3	101.45 (4)
N1—Zn1—Cl1	96.55 (4)	N6—Zn2—Cl3	99.99 (4)
Cl2—Zn1—Cl1	110.650 (15)	Cl4—Zn2—Cl3	120.032 (16)
C1—N1—C5	118.83 (14)	C12—N4—C16	119.00 (13)
C1—N1—Zn1	125.76 (11)	C12—N4—Zn2	126.29 (11)
C5—N1—Zn1	115.39 (10)	C16—N4—Zn2	114.65 (10)
C6—N2—C8	123.84 (14)	C17—N5—C19	123.13 (14)
C6—N2—Zn1	120.07 (11)	C17—N5—Zn2	120.03 (11)
C8—N2—Zn1	115.79 (10)	C19—N5—Zn2	116.78 (10)
C11—N3—C9	111.07 (12)	C21—N6—C22	109.24 (13)
C11—N3—C10	108.91 (12)	C21—N6—C20	110.95 (13)
C9—N3—C10	109.76 (12)	C22—N6—C20	110.13 (13)
C11—N3—Zn1	110.89 (9)	C21—N6—Zn2	111.83 (10)
C9—N3—Zn1	104.09 (9)	C22—N6—Zn2	112.01 (11)
C10—N3—Zn1	112.07 (10)	C20—N6—Zn2	102.55 (9)
N1—C1—C2	122.36 (16)	N4—C12—C13	122.15 (16)
N1—C1—H1	118.8	N4—C12—H12	118.9
C2—C1—H1	118.8	C13—C12—H12	118.9
C3—C2—C1	118.86 (16)	C14—C13—C12	119.16 (15)
C3—C2—H2	120.6	C14—C13—H13	120.4
C1—C2—H2	120.6	C12—C13—H13	120.4
C2—C3—C4	119.06 (16)	C13—C14—C15	118.84 (15)
C2—C3—H3	120.5	C13—C14—H14	120.6
C4—C3—H3	120.5	C15—C14—H14	120.6
C3—C4—C5	119.25 (16)	C16—C15—C14	118.83 (15)
C3—C4—H4	120.4	C16—C15—H15	120.6
C5—C4—H4	120.4	C14—C15—H15	120.6
N1—C5—C4	121.63 (15)	N4—C16—C15	122.01 (14)
N1—C5—C6	114.84 (13)	N4—C16—C17	114.84 (13)
C4—C5—C6	123.48 (15)	C15—C16—C17	123.13 (14)
N2—C6—C5	114.69 (14)	N5—C17—C18	125.30 (14)
N2—C6—C7	126.21 (15)	N5—C17—C16	115.18 (14)
C5—C6—C7	119.10 (14)	C18—C17—C16	119.51 (13)
C6—C7—H7A	109.5	C17—C18—H18A	109.5
C6—C7—H7B	109.5	C17—C18—H18B	109.5
H7A—C7—H7B	109.5	H18A—C18—H18B	109.5
C6—C7—H7C	109.5	C17—C18—H18C	109.5
H7A—C7—H7C	109.5	H18A—C18—H18C	109.5
H7B—C7—H7C	109.5	H18B—C18—H18C	109.5
N2—C8—C9	107.67 (12)	N5—C19—C20	107.57 (13)
N2—C8—H8A	110.2	N5—C19—H19A	110.2
C9—C8—H8A	110.2	C20—C19—H19A	110.2
N2—C8—H8B	110.2	N5—C19—H19B	110.2
C9—C8—H8B	110.2	C20—C19—H19B	110.2
H8A—C8—H8B	108.5	H19A—C19—H19B	108.5
N3—C9—C8	111.57 (13)	N6—C20—C19	111.55 (13)
N3—C9—H9A	109.3	N6—C20—H20A	109.3
C8—C9—H9A	109.3	C19—C20—H20A	109.3
N3—C9—H9B	109.3	N6—C20—H20B	109.3
C8—C9—H9B	109.3	C19—C20—H20B	109.3
H9A—C9—H9B	108.0	H20A—C20—H20B	108.0
N3—C10—H10A	109.5	N6—C21—H21A	109.5
N3—C10—H10B	109.5	N6—C21—H21B	109.5
H10A—C10—H10B	109.5	H21A—C21—H21B	109.5
N3—C10—H10C	109.5	N6—C21—H21C	109.5
H10A—C10—H10C	109.5	H21A—C21—H21C	109.5
H10B—C10—H10C	109.5	H21B—C21—H21C	109.5
N3—C11—H11A	109.5	N6—C22—H22A	109.5
N3—C11—H11B	109.5	N6—C22—H22B	109.5
H11A—C11—H11B	109.5	H22A—C22—H22B	109.5
N3—C11—H11C	109.5	N6—C22—H22C	109.5
H11A—C11—H11C	109.5	H22A—C22—H22C	109.5
H11B—C11—H11C	109.5	H22B—C22—H22C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cl2ⁱ	0.95	2.79	3.6690 (17)	155
C8—H8A···Cl1ⁱⁱ	0.99	2.63	3.5668 (16)	158
C8—H8B···Cl2ⁱⁱⁱ	0.99	2.73	3.6564 (16)	156
C11—H11A···Cl2ⁱⁱⁱ	0.98	2.77	3.6573 (17)	151
C15—H15···Cl2^iv	0.95	2.74	3.6347 (17)	157
C18—H18B···Cl1^iv	0.98	2.75	3.7227 (17)	175
C19—H19B···Cl4^v	0.99	2.82	3.8089 (16)	174

Symmetry codes: (i) −x, −y+1, −z; (ii) −x, y−1/2, −z+1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x+1, −y+1, −z+1; (v) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[ZnCl₂(C₁₁H₁₇N₃)]
M_r	327.55
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	17.4849 (8), 9.8161 (4), 20.4264 (7)
β (°)	124.578 (3)
V (Å³)	2886.6 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.05
Crystal size (mm)	0.27 × 0.23 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.607, 0.748
No. of measured, independent and observed [I > 2σ(I)] reflections	20477, 6294, 5510
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.052, 1.04
No. of reflections	6294
No. of parameters	313
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).