Bis(10-meth­oxy­benzo[h]quinolinium) tetra­chloridozinc

Dong, Z.; Liu, B.

doi:10.1107/S1600536811055462

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page m131

doi:10.1107/S1600536811055462

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Bis(10-methoxybenzo[h]quinolinium) tetrachloridozinc

Zhenming Dong ^a and Bo Liu ^b ^*

^aSchool of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, People's Republic of China, and ^bInstitute of Chemistry, School of Science, Beijing Jiaotong University, Beijing 100044, People's Republic of China
^*Correspondence e-mail: liubo4314@yahoo.com.cn

(Received 16 December 2011; accepted 23 December 2011; online 11 January 2012)

In the title compound, (C₁₄H₁₂NO)₂[ZnCl₄], the benzo[h]quinolinium groups are approximately planar, with maximum deviations of 0.049 (8) and 0.056 (9) Å. The methoxy groups are stabilized by intramolecular N—H⋯O hydrogen bonds. The structure also exhibits weak intermolecular N—H⋯Cl hydrogen bonds between the cations and anions. π–π interactions are present between the pyridinium and benzene rings [centroid–centroid distances = 3.640 (4), 3.728 (5) and 3.628 (5) Å].

Related literature

For background to quinoline derivatives, see: Kouznetsov et al. (2005 ). For related complexes, see: Guo et al. (2007 ).

Experimental

Crystal data

(C₁₄H₁₂NO)₂[ZnCl₄]
M_r = 627.66
Triclinic, $[P \overline 1]$
a = 8.3846 (15) Å
b = 9.6352 (18) Å
c = 18.348 (3) Å
α = 91.810 (3)°
β = 92.508 (3)°
γ = 114.967 (3)°
V = 1340.4 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.35 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.688, T_max = 0.775
5013 measured reflections
4177 independent reflections
3432 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.220
S = 1.18
4177 reflections
337 parameters
H-atom parameters constrained
Δρ_max = 0.92 e Å⁻³
Δρ_min = −0.85 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	1.95	2.612 (7)	133
N1—H1⋯Cl1ⁱ	0.86	2.68	3.319 (6)	132
N2—H2⋯O2	0.86	1.93	2.598 (7)	134
N2—H2⋯Cl2ⁱⁱ	0.86	2.84	3.472 (6)	132
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811055462/hy2499sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055462/hy2499Isup2.hkl

checkCIF report

Comment top

Quinoline derivatives represent a major class of heterocycles, and a number of preparations have been known since the late 1800s (Kouznetsov et al., 2005). The quinoline ring system occurs in various natural products, especially in alkaloids (Kouznetsov et al., 2005). In the course of exploring new quinoline complexes (Guo et al., 2007), we obtained the title compound and the synthesis and structure are reported here.

In the title compound (Fig. 1), the benzo[h]quinolinium groups are planar, with maximum deviations from the average planes of 0.049 (8) and 0.056 (9) Å, respectively. The methoxy groups are stabilized by intramolecular N—H···O hydrogen bonds (Table 1). The structure also exhibits week intermolecular N—H···Cl hydrogen bonds between the cations and anions. π–π interactions are present between the pyridinium and benzene rings [centroid–centroid distances = 3.640 (4), 3.728 (5) and 3.628 (5) Å].

Related literature top

For background to quinoline derivatives, see: Kouznetsov et al. (2005). For related complexes, see: Guo et al. (2007).

Experimental top

10-Methoxybenzo[h]quinoline (0.30 g, 1.43 mmol) was dissolved in THF (20 ml) and ZnCl₂ (0.20 g, 1.48 mmol) was added. The mixture was heated with stirring at reflux temperature for 8 h, then cooled to 333 K and filtered. The filtrate was condenced to get yellow crystals suitable for X-ray analysis.

Computing details top

Data collection: SMART (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: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

Bis(10-methoxybenzo[h]quinolinium) tetrachloridozinc top

Crystal data top

(C₁₄H₁₂NO)₂[ZnCl₄]	Z = 2
M_r = 627.66	F(000) = 640
Triclinic, P1	D_x = 1.555 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3846 (15) Å	Cell parameters from 2730 reflections
b = 9.6352 (18) Å	θ = 2.2–27.5°
c = 18.348 (3) Å	µ = 1.35 mm⁻¹
α = 91.810 (3)°	T = 293 K
β = 92.508 (3)°	Block, yellow
γ = 114.967 (3)°	0.30 × 0.20 × 0.20 mm
V = 1340.4 (4) Å³

Data collection top

Bruker APEX CCD diffractometer	4177 independent reflections
Radiation source: fine-focus sealed tube	3432 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 24.3°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.688, T_max = 0.775	k = −11→5
5013 measured reflections	l = −21→21

Refinement top

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)] = 0.073	H-atom parameters constrained
wR(F²) = 0.220	w = 1/[σ²(F_o²) + (0.118P)² + 1.3115P] where P = (F_o² + 2F_c²)/3
S = 1.18	(Δ/σ)_max < 0.001
4177 reflections	Δρ_max = 0.92 e Å⁻³
337 parameters	Δρ_min = −0.85 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.027 (5)

Crystal data top

(C₁₄H₁₂NO)₂[ZnCl₄]	γ = 114.967 (3)°
M_r = 627.66	V = 1340.4 (4) Å³
Triclinic, P1	Z = 2
a = 8.3846 (15) Å	Mo Kα radiation
b = 9.6352 (18) Å	µ = 1.35 mm⁻¹
c = 18.348 (3) Å	T = 293 K
α = 91.810 (3)°	0.30 × 0.20 × 0.20 mm
β = 92.508 (3)°

Data collection top

Bruker APEX CCD diffractometer	4177 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3432 reflections with I > 2σ(I)
T_min = 0.688, T_max = 0.775	R_int = 0.028
5013 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.220	H-atom parameters constrained
S = 1.18	Δρ_max = 0.92 e Å⁻³
4177 reflections	Δρ_min = −0.85 e Å⁻³
337 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	0.65848 (11)	0.46816 (9)	0.25386 (4)	0.0402 (4)
Cl1	0.4662 (3)	0.3566 (2)	0.34307 (9)	0.0479 (5)
Cl2	0.5032 (3)	0.5538 (2)	0.17408 (10)	0.0491 (5)
Cl3	0.7041 (4)	0.2815 (3)	0.19234 (12)	0.0686 (7)
Cl4	0.9008 (3)	0.6651 (3)	0.30484 (12)	0.0639 (6)
O1	0.2911 (7)	1.1282 (5)	0.4863 (3)	0.0443 (12)
O2	1.2012 (6)	0.4167 (5)	0.0191 (3)	0.0447 (12)
N1	0.3863 (7)	0.9990 (6)	0.3799 (3)	0.0362 (13)
H1	0.3811	1.0809	0.3972	0.043*
N2	1.1219 (7)	0.2271 (6)	0.1233 (3)	0.0403 (14)
H2	1.1914	0.3149	0.1088	0.048*
C7	0.2315 (8)	0.9970 (7)	0.5249 (4)	0.0339 (15)
C11	0.2044 (9)	0.7392 (8)	0.5306 (4)	0.0383 (16)
C19	0.8652 (9)	−0.0063 (8)	0.1046 (4)	0.0400 (17)
C5	0.3231 (8)	0.8696 (7)	0.4211 (4)	0.0334 (15)
C22	1.0506 (9)	0.3249 (8)	−0.0213 (4)	0.0371 (16)
C4	0.3342 (9)	0.7386 (7)	0.3914 (4)	0.0367 (16)
C6	0.2526 (8)	0.8717 (7)	0.4925 (3)	0.0307 (14)
C20	0.9774 (8)	0.1375 (7)	0.0789 (4)	0.0322 (15)
C18	0.9075 (10)	−0.0513 (8)	0.1711 (4)	0.0471 (19)
H18	0.8338	−0.1454	0.1883	0.056*
C1	0.4544 (10)	1.0034 (9)	0.3153 (4)	0.0453 (18)
H1A	0.4953	1.0933	0.2903	0.054*
C13	0.2790 (10)	0.6069 (8)	0.4329 (5)	0.0493 (19)
H13	0.2863	0.5195	0.4136	0.059*
C21	0.9408 (8)	0.1852 (8)	0.0091 (4)	0.0348 (15)
C26	0.7838 (9)	0.0852 (8)	−0.0321 (4)	0.0418 (17)
C10	0.1336 (10)	0.7295 (9)	0.5993 (4)	0.0486 (18)
H10	0.1017	0.6412	0.6251	0.058*
C3	0.4010 (10)	0.7407 (9)	0.3237 (4)	0.0468 (18)
H3	0.4039	0.6521	0.3035	0.056*
C8	0.1616 (10)	0.9881 (8)	0.5903 (4)	0.0447 (18)
H8	0.1463	1.0710	0.6106	0.054*
C9	0.1130 (11)	0.8546 (10)	0.6269 (4)	0.058 (2)
H9	0.0645	0.8492	0.6719	0.070*
C17	1.0585 (11)	0.0437 (10)	0.2115 (4)	0.055 (2)
H17	1.0911	0.0117	0.2546	0.066*
C2	0.4640 (10)	0.8740 (9)	0.2854 (4)	0.0488 (19)
H2A	0.5118	0.8758	0.2405	0.059*
C14	0.2706 (11)	1.2609 (8)	0.5156 (4)	0.0487 (19)
H14A	0.1477	1.2350	0.5198	0.073*
H14B	0.3188	1.3432	0.4834	0.073*
H14C	0.3318	1.2922	0.5629	0.073*
C29	1.3189 (10)	0.5596 (8)	−0.0091 (4)	0.0451 (17)
H29A	1.3556	0.5398	−0.0556	0.068*
H29B	1.4203	0.6093	0.0243	0.068*
H29C	1.2591	0.6247	−0.0149	0.068*
C12	0.2156 (10)	0.6040 (8)	0.5000 (4)	0.0455 (18)
H12	0.1797	0.5156	0.5260	0.055*
C16	1.1615 (10)	0.1866 (9)	0.1877 (4)	0.0491 (19)
H16	1.2586	0.2545	0.2167	0.059*
C25	0.7424 (10)	0.1275 (9)	−0.1000 (4)	0.0482 (19)
H25	0.6393	0.0628	−0.1268	0.058*
C23	1.0090 (10)	0.3623 (9)	−0.0891 (4)	0.0457 (18)
H23	1.0846	0.4524	−0.1090	0.055*
C28	0.7095 (10)	−0.1024 (9)	0.0607 (5)	0.052 (2)
H28	0.6328	−0.1964	0.0770	0.062*
C27	0.6748 (10)	−0.0574 (9)	−0.0032 (5)	0.050 (2)
H27	0.5735	−0.1227	−0.0309	0.060*
C24	0.8520 (10)	0.2638 (10)	−0.1279 (4)	0.051 (2)
H24	0.8216	0.2906	−0.1729	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0497 (6)	0.0382 (5)	0.0349 (5)	0.0200 (4)	0.0069 (4)	0.0055 (3)
Cl1	0.0652 (12)	0.0475 (11)	0.0383 (10)	0.0292 (9)	0.0152 (8)	0.0111 (8)
Cl2	0.0621 (12)	0.0488 (11)	0.0392 (10)	0.0258 (9)	0.0029 (8)	0.0073 (8)
Cl3	0.1108 (19)	0.0549 (13)	0.0580 (13)	0.0491 (13)	0.0347 (12)	0.0140 (10)
Cl4	0.0558 (13)	0.0597 (14)	0.0627 (13)	0.0122 (10)	−0.0040 (10)	0.0037 (11)
O1	0.066 (3)	0.034 (3)	0.044 (3)	0.031 (2)	0.010 (2)	0.002 (2)
O2	0.042 (3)	0.032 (3)	0.047 (3)	0.002 (2)	0.002 (2)	0.008 (2)
N1	0.042 (3)	0.036 (3)	0.035 (3)	0.021 (3)	0.002 (2)	0.004 (2)
N2	0.043 (3)	0.033 (3)	0.038 (3)	0.009 (3)	0.004 (3)	0.006 (3)
C7	0.030 (3)	0.032 (4)	0.042 (4)	0.015 (3)	0.002 (3)	0.005 (3)
C11	0.035 (4)	0.039 (4)	0.041 (4)	0.016 (3)	−0.004 (3)	0.005 (3)
C19	0.040 (4)	0.035 (4)	0.048 (4)	0.017 (3)	0.012 (3)	0.002 (3)
C5	0.034 (4)	0.030 (4)	0.040 (4)	0.018 (3)	−0.002 (3)	−0.002 (3)
C22	0.036 (4)	0.033 (4)	0.040 (4)	0.012 (3)	0.008 (3)	0.003 (3)
C4	0.036 (4)	0.027 (4)	0.046 (4)	0.013 (3)	−0.004 (3)	−0.002 (3)
C6	0.028 (3)	0.027 (3)	0.036 (3)	0.010 (3)	−0.001 (3)	0.007 (3)
C20	0.028 (3)	0.027 (3)	0.039 (4)	0.011 (3)	0.003 (3)	−0.005 (3)
C18	0.046 (4)	0.034 (4)	0.058 (5)	0.013 (4)	0.020 (4)	0.008 (4)
C1	0.054 (5)	0.048 (4)	0.040 (4)	0.027 (4)	0.003 (3)	0.010 (3)
C13	0.049 (4)	0.036 (4)	0.071 (5)	0.026 (4)	0.004 (4)	−0.006 (4)
C21	0.027 (3)	0.034 (4)	0.042 (4)	0.011 (3)	0.005 (3)	−0.002 (3)
C26	0.034 (4)	0.041 (4)	0.050 (4)	0.015 (3)	0.013 (3)	−0.003 (3)
C10	0.056 (5)	0.042 (4)	0.051 (4)	0.024 (4)	0.002 (4)	0.010 (4)
C3	0.055 (5)	0.043 (4)	0.049 (4)	0.028 (4)	−0.003 (3)	−0.010 (4)
C8	0.054 (5)	0.037 (4)	0.049 (4)	0.023 (4)	0.015 (4)	0.007 (3)
C9	0.067 (5)	0.067 (6)	0.044 (4)	0.031 (5)	0.018 (4)	0.000 (4)
C17	0.070 (6)	0.064 (6)	0.038 (4)	0.034 (5)	0.010 (4)	0.016 (4)
C2	0.058 (5)	0.063 (5)	0.036 (4)	0.035 (4)	0.003 (3)	−0.005 (4)
C14	0.076 (5)	0.031 (4)	0.051 (4)	0.034 (4)	0.003 (4)	−0.005 (3)
C29	0.043 (4)	0.033 (4)	0.047 (4)	0.004 (3)	0.007 (3)	0.006 (3)
C12	0.054 (5)	0.037 (4)	0.054 (5)	0.027 (4)	0.003 (4)	0.007 (3)
C16	0.041 (4)	0.056 (5)	0.042 (4)	0.012 (4)	0.000 (3)	0.006 (4)
C25	0.038 (4)	0.050 (5)	0.047 (4)	0.012 (4)	−0.006 (3)	−0.004 (4)
C23	0.046 (4)	0.044 (4)	0.041 (4)	0.013 (4)	0.008 (3)	0.007 (3)
C28	0.041 (4)	0.034 (4)	0.070 (6)	0.005 (3)	0.014 (4)	0.013 (4)
C27	0.034 (4)	0.036 (4)	0.064 (5)	−0.001 (3)	0.007 (3)	−0.006 (4)
C24	0.054 (5)	0.060 (5)	0.037 (4)	0.023 (4)	−0.009 (3)	0.003 (4)

Geometric parameters (Å, º) top

Zn1—Cl4	2.252 (2)	C1—H1A	0.9300
Zn1—Cl3	2.268 (2)	C13—C12	1.359 (11)
Zn1—Cl1	2.305 (2)	C13—H13	0.9300
Zn1—Cl2	2.310 (2)	C21—C26	1.425 (10)
O1—C7	1.380 (8)	C26—C25	1.398 (11)
O1—C14	1.449 (8)	C26—C27	1.426 (11)
O2—C22	1.364 (8)	C10—C9	1.373 (11)
O2—C29	1.442 (8)	C10—H10	0.9300
N1—C1	1.332 (9)	C3—C2	1.392 (11)
N1—C5	1.395 (9)	C3—H3	0.9300
N1—H1	0.8600	C8—C9	1.381 (11)
N2—C16	1.327 (9)	C8—H8	0.9300
N2—C20	1.365 (8)	C9—H9	0.9300
N2—H2	0.8600	C17—C16	1.378 (11)
C7—C8	1.348 (10)	C17—H17	0.9300
C7—C6	1.410 (9)	C2—H2A	0.9300
C11—C6	1.389 (9)	C14—H14A	0.9600
C11—C12	1.443 (10)	C14—H14B	0.9600
C11—C10	1.405 (10)	C14—H14C	0.9600
C19—C18	1.389 (11)	C29—H29A	0.9600
C19—C20	1.417 (10)	C29—H29B	0.9600
C19—C28	1.432 (11)	C29—H29C	0.9600
C5—C4	1.399 (9)	C12—H12	0.9300
C5—C6	1.463 (9)	C16—H16	0.9300
C22—C21	1.421 (9)	C25—C24	1.376 (11)
C22—C23	1.376 (10)	C25—H25	0.9300
C4—C3	1.381 (10)	C23—C24	1.401 (11)
C4—C13	1.414 (10)	C23—H23	0.9300
C20—C21	1.437 (10)	C28—C27	1.326 (12)
C18—C17	1.373 (11)	C28—H28	0.9300
C18—H18	0.9300	C27—H27	0.9300
C1—C2	1.381 (10)	C24—H24	0.9300

Cl4—Zn1—Cl3	116.13 (10)	C21—C26—C27	118.7 (7)
Cl4—Zn1—Cl1	109.32 (8)	C9—C10—C11	117.8 (7)
Cl3—Zn1—Cl1	108.22 (8)	C9—C10—H10	121.1
Cl4—Zn1—Cl2	111.04 (8)	C11—C10—H10	121.1
Cl3—Zn1—Cl2	107.14 (8)	C4—C3—C2	120.8 (6)
Cl1—Zn1—Cl2	104.30 (8)	C4—C3—H3	119.6
C7—O1—C14	118.7 (5)	C2—C3—H3	119.6
C22—O2—C29	119.1 (5)	C7—C8—C9	119.3 (7)
C1—N1—C5	123.9 (6)	C7—C8—H8	120.3
C1—N1—H1	118.1	C9—C8—H8	120.3
C5—N1—H1	118.1	C10—C9—C8	122.4 (7)
C16—N2—C20	123.9 (6)	C10—C9—H9	118.8
C16—N2—H2	118.0	C8—C9—H9	118.8
C20—N2—H2	118.0	C18—C17—C16	119.8 (7)
C8—C7—O1	123.1 (6)	C18—C17—H17	120.1
C8—C7—C6	121.3 (6)	C16—C17—H17	120.1
O1—C7—C6	115.6 (6)	C1—C2—C3	118.9 (7)
C6—C11—C12	121.7 (6)	C1—C2—H2A	120.5
C6—C11—C10	120.8 (6)	C3—C2—H2A	120.5
C12—C11—C10	117.4 (7)	O1—C14—H14A	109.5
C18—C19—C20	119.9 (6)	O1—C14—H14B	109.5
C18—C19—C28	121.4 (7)	H14A—C14—H14B	109.5
C20—C19—C28	118.7 (7)	O1—C14—H14C	109.5
C4—C5—N1	116.5 (6)	H14A—C14—H14C	109.5
C4—C5—C6	121.7 (6)	H14B—C14—H14C	109.5
N1—C5—C6	121.7 (5)	O2—C29—H29A	109.5
O2—C22—C21	116.4 (6)	O2—C29—H29B	109.5
O2—C22—C23	122.2 (6)	H29A—C29—H29B	109.5
C21—C22—C23	121.4 (6)	O2—C29—H29C	109.5
C3—C4—C5	120.1 (7)	H29A—C29—H29C	109.5
C3—C4—C13	121.5 (6)	H29B—C29—H29C	109.5
C5—C4—C13	118.4 (6)	C13—C12—C11	119.5 (7)
C11—C6—C7	118.3 (6)	C13—C12—H12	120.3
C11—C6—C5	116.5 (6)	C11—C12—H12	120.3
C7—C6—C5	125.1 (6)	N2—C16—C17	119.8 (7)
N2—C20—C19	116.7 (6)	N2—C16—H16	120.1
N2—C20—C21	122.0 (6)	C17—C16—H16	120.1
C19—C20—C21	121.3 (6)	C24—C25—C26	120.9 (7)
C17—C18—C19	119.7 (7)	C24—C25—H25	119.6
C17—C18—H18	120.2	C26—C25—H25	119.6
C19—C18—H18	120.2	C24—C23—C22	119.6 (7)
N1—C1—C2	119.8 (7)	C24—C23—H23	120.2
N1—C1—H1A	120.1	C22—C23—H23	120.2
C2—C1—H1A	120.1	C27—C28—C19	119.9 (7)
C12—C13—C4	122.1 (6)	C27—C28—H28	120.0
C12—C13—H13	118.9	C19—C28—H28	120.0
C4—C13—H13	118.9	C28—C27—C26	123.8 (7)
C22—C21—C20	124.4 (6)	C28—C27—H27	118.1
C22—C21—C26	118.0 (6)	C26—C27—H27	118.1
C20—C21—C26	117.6 (6)	C25—C24—C23	120.6 (7)
C25—C26—C21	119.5 (7)	C25—C24—H24	119.7
C25—C26—C27	121.8 (7)	C23—C24—H24	119.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.95	2.612 (7)	133
N1—H1···Cl1ⁱ	0.86	2.68	3.319 (6)	132
N2—H2···O2	0.86	1.93	2.598 (7)	134
N2—H2···Cl2ⁱⁱ	0.86	2.84	3.472 (6)	132

Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	(C₁₄H₁₂NO)₂[ZnCl₄]
M_r	627.66
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.3846 (15), 9.6352 (18), 18.348 (3)
α, β, γ (°)	91.810 (3), 92.508 (3), 114.967 (3)
V (Å³)	1340.4 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.35
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.688, 0.775
No. of measured, independent and observed [I > 2σ(I)] reflections	5013, 4177, 3432
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.578

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.220, 1.18
No. of reflections	4177
No. of parameters	337
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.92, −0.85

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.95	2.612 (7)	133
N1—H1···Cl1ⁱ	0.86	2.68	3.319 (6)	132
N2—H2···O2	0.86	1.93	2.598 (7)	134
N2—H2···Cl2ⁱⁱ	0.86	2.84	3.472 (6)	132

Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.

Acknowledgements

The authors are grateful to the National Natural Science Foundation of China (grant No. 21072019) for supporting this work.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Guo, Z., Dong, Z., Zhu, R., Jin, S. & Liu, B. (2007). Spectrochim. Acta Part A, 68, 337–340. CrossRef Google Scholar
Kouznetsov, V. V., Méndez, L. Y. V. & Gómez, C. M. M. (2005). Curr. Org. Chem. 9, 141–161. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar