Di­chlorido­(N,N-diethyl-4-{[(quinolin-2-yl)methyl­idene]amino-κ2N,N′}aniline)mercury(II)

Faizi, M.S.H.; Hussain, S.

doi:10.1107/S160053681400957X

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Page m197

doi:10.1107/S160053681400957X

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Dichlorido(N,N-diethyl-4-{[(quinolin-2-yl)methylidene]amino-κ²N,N′}aniline)mercury(II)

Md. Serajul Haque Faizi ^a and Sahid Hussain ^b ^*

^aDepartment of Chemistry, Indian Institute of Technology Kanpur, Kanpur, UP 208 016, India, and ^bDepartment of Chemistry, Indian Institute of Technology Patna, Patna, Bihar 800 013, India
^*Correspondence e-mail: sahid@iitp.ac.in

(Received 6 April 2014; accepted 28 April 2014; online 3 May 2014)

In the mononuclear title complex, [HgCl₂(C₂₀H₂₁N₃)], synthesized from the quinoline-derived Schiff base N¹,N¹-diethyl-N⁴-(quinolin-2-ylmethylidene)benzene-1,4-diamine (QMBD), the coordination geometry around the Hg²⁺ atom is distorted tetrahedral, comprising two Cl atoms [Hg—Cl = 2.3654 (19) and 2.4394 (18) Å] and two N-atom donors from the QMBD ligand, viz. one imine and quinoline [Hg—N = 2.334 (5) and 2.340 (5) Å, respectively]. In the crystal, weak C—H⋯Cl hydrogen bonds and weak π–π aromatic ring stacking interactions [minimum ring-centroid separation = 3.680 (4) Å] give an overall three-dimensional network.

CCDC reference: 999849

Related literature

For applications of quinolyl imine and related structures, see: Mandal et al. (2012 ); Motswainyana et al. (2013 ); Das et al. (2013 ); Song et al. (2011 ); Jursic et al. (2002 ); Marjani et al. (2009 ); Faizi & Sen (2014 ).

Experimental

Crystal data

[HgCl₂(C₂₀H₂₁N₃)]
M_r = 574.89
Monoclinic, P 2₁ /n
a = 8.8522 (19) Å
b = 9.474 (2) Å
c = 23.512 (5) Å
β = 97.446 (4)°
V = 1955.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 8.15 mm⁻¹
T = 100 K
0.26 × 0.18 × 0.13 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.226, T_max = 0.417
9875 measured reflections
3438 independent reflections
2979 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.089
S = 1.17
3438 reflections
233 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.91 e Å⁻³
Δρ_min = −1.07 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cl2ⁱ	0.93	2.82	3.703 (7)	159
C15—H15⋯Cl1ⁱⁱ	0.93	2.82	3.715 (7)	162
Symmetry codes: (i) -x+2, -y, -z+2; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2006 ); software used to prepare material for publication: DIAMOND.

Supporting information

CCDC reference: 999849

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681400957X/zs2295sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681400957X/zs2295Isup2.hkl

checkCIF report

Comment top

Mercury is one of the most prevalent toxic metals in the environment and gains access to the body orally or dermally, causing cell dysfunction that consequently leads to health problems (Mandal et al., 2012). Quinolyl derivatives of Schiff bases are important building blocks for many important compounds widely used in biological applications such as antioxidative, anticancer, fluorescent probe agents in industry, in coordination chemistry and in catalysis (Motswainyana et al., 2013; Das et al., 2013; Song et al., 2011; Jursic et al., 2002). The synthesis of a complex of mercury(II) using the quinoline aldehyde derivative of the Schiff base N¹,N¹-diethyl-N⁴- (quinolin-2-ylmethylene-1,4-diamine (QMBD) has not previously been reported. The title Hg^II complex with QMBD, [Hg(C₂₀H₂₁N₃)Cl₂] has now been synthesized and the structure is reported herein.

In the title mononuclear complex (Figs. 1, 2) the HgCl₂N₂ coordination geometry is distorted tetrahedral, comprising two Cl-atoms [Hg1—Cl1 and Hg1—Cl2 = 2.3654 (19) and 2.4394 (18) Å respectively] and two N-atom donors from the QMBD ligand, one imine [Hg1–N2 = 2.334 (5) Å] and the other quinoline [Hg1—N1 = 2.340 (5) Å]. The observed Hg—Cl and Hg—N bond lengths and bond angles are considered normal for this type of Hg^II complex, e.g. (Marjani et al., 2009; Faizi & Sen, 2014). In the crystal, weak C12—H···Cl2ⁱ [3.703 (7) Å] and C15—H···Cl1ⁱⁱ [3.715 (7) Å hydrogen bonds (Table 1) and π–π aromatic ring stacking interactions [minimum ring centroid separation between the quinoline ring moiety defined by atoms N1–C9 = 3.680 (4) Å] give an overall three-dimensional framework structure (Figs. 3, 4).

Related literature top

For applications of quinolyl imine and related structures, see: Mandal et al. (2012); Motswainyana et al. (2013); Das et al. (2013); Song et al. (2011); Jursic et al. (2002); Marjani et al. (2009); Faizi & Sen (2014).

Experimental top

The iminoquinolyl compound N¹,N¹-diethyl-N⁴-(quinolin-2-ylmethylidene)benzene-1,4-diamine (QMBD) was prepared by reacting 2-quinolinecarboxaldehyde with a substituted aniline and was obtained in very good yields. This compound was characterized by FT—IR, NMR and ESI-Mass spectroscopy. A mixture of QMBD (0.10 g, 0.33 mmol), mercury(II) chloride (0.09 g, 0.33 mmol) and ethanol (5 ml) were stirred vigorously for 1 h, after which the precipitate was filtered off and redissolved in dimethylformamide. Crystals of the title complex suitable for X-ray analysis was obtained within 3 days by slow evaporation of the DMF solvent.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2006); software used to prepare material for publication: DIAMOND (Brandenburg & Putz, 2006).

Figures top

	Fig. 1. The molecular conformation and atom-numbering scheme for the title complex with non-H atoms drawn as 30% probability displacement ellipsoids.
	Fig. 2. A further view of the title complex.
	Fig. 3. The one-dimensional weak interactive chain structure in the title complex extending along the approximate c-cell direction, with associations shown as dashed lines.
	Fig. 4. The structure viewed along the a-cell direction.

Dichlorido(N,N-diethyl-4-{[(quinolin-2-yl)methylidene]amino-κ²N,N'}aniline)mercury(II) top

Crystal data top

[HgCl₂(C₂₀H₂₁N₃)]	F(000) = 1104
M_r = 574.89	D_x = 1.953 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 999 reflections
a = 8.8522 (19) Å	θ = 2.1–28.2°
b = 9.474 (2) Å	µ = 8.15 mm⁻¹
c = 23.512 (5) Å	T = 100 K
β = 97.446 (4)°	Block, yellow
V = 1955.2 (7) Å³	0.26 × 0.18 × 0.13 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	3438 independent reflections
Radiation source: fine-focus sealed tube	2979 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→7
T_min = 0.226, T_max = 0.417	k = −11→11
9875 measured reflections	l = −27→27

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ²(F_o²) + (0.0308P)² + 10.3789P] where P = (F_o² + 2F_c²)/3
3438 reflections	(Δ/σ)_max < 0.001
233 parameters	Δρ_max = 1.91 e Å⁻³
0 restraints	Δρ_min = −1.07 e Å⁻³

Crystal data top

[HgCl₂(C₂₀H₂₁N₃)]	V = 1955.2 (7) Å³
M_r = 574.89	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.8522 (19) Å	µ = 8.15 mm⁻¹
b = 9.474 (2) Å	T = 100 K
c = 23.512 (5) Å	0.26 × 0.18 × 0.13 mm
β = 97.446 (4)°

Data collection top

Bruker SMART APEX CCD diffractometer	3438 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2979 reflections with I > 2σ(I)
T_min = 0.226, T_max = 0.417	R_int = 0.034
9875 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ²(F_o²) + (0.0308P)² + 10.3789P] where P = (F_o² + 2F_c²)/3
3438 reflections	Δρ_max = 1.91 e Å⁻³
233 parameters	Δρ_min = −1.07 e Å⁻³

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
C1	0.8207 (7)	0.4421 (7)	1.0240 (3)	0.0184 (10)
C2	0.6971 (8)	0.5234 (7)	0.9970 (3)	0.0225 (15)
H2	0.6564	0.5035	0.9594	0.027*
C3	0.6374 (8)	0.6313 (7)	1.0260 (3)	0.0253 (16)
H3	0.5575	0.6853	1.0078	0.030*
C4	0.6962 (8)	0.6602 (7)	1.0826 (3)	0.0221 (15)
H4	0.6540	0.7326	1.1021	0.027*
C5	0.8150 (9)	0.5836 (7)	1.1100 (3)	0.0268 (16)
H5	0.8521	0.6041	1.1479	0.032*
C6	0.8819 (8)	0.4740 (7)	1.0813 (3)	0.0218 (15)
C7	1.0050 (8)	0.3942 (6)	1.1069 (3)	0.0211 (14)
H7	1.0451	0.4107	1.1448	0.025*
C8	1.0667 (7)	0.2912 (7)	1.0759 (3)	0.0198 (14)
H8	1.1509	0.2398	1.0921	0.024*
C9	0.9991 (8)	0.2638 (6)	1.0179 (3)	0.0171 (14)
C10	1.0694 (7)	0.1553 (7)	0.9856 (3)	0.0184 (10)
C11	1.0772 (7)	0.0274 (6)	0.9004 (3)	0.0169 (13)
C12	1.2176 (8)	−0.0386 (6)	0.9159 (3)	0.0198 (14)
H12	1.2724	−0.0179	0.9514	0.024*
C13	1.2770 (8)	−0.1323 (7)	0.8809 (3)	0.0230 (15)
H13	1.3710	−0.1732	0.8933	0.028*
C14	1.2006 (8)	−0.1695 (7)	0.8265 (3)	0.0201 (14)
C15	1.0599 (7)	−0.1020 (6)	0.8098 (3)	0.0167 (13)
H15	1.0055	−0.1227	0.7742	0.020*
C16	1.0010 (8)	−0.0056 (7)	0.8452 (3)	0.0190 (14)
H16	0.9091	0.0388	0.8325	0.023*
C17	1.4009 (8)	−0.3421 (7)	0.8108 (3)	0.0236 (15)
H17A	1.3981	−0.4306	0.7899	0.028*
H17B	1.4031	−0.3645	0.8512	0.028*
C18	1.5448 (9)	−0.2657 (7)	0.8027 (4)	0.0333 (19)
H18A	1.6310	−0.3233	0.8165	0.050*
H18B	1.5498	−0.1786	0.8237	0.050*
H18C	1.5457	−0.2462	0.7627	0.050*
C19	1.1893 (9)	−0.2913 (7)	0.7336 (3)	0.0261 (16)
H19A	1.2676	−0.3201	0.7107	0.031*
H19B	1.1440	−0.2049	0.7171	0.031*
C20	1.0669 (8)	−0.4057 (7)	0.7300 (3)	0.0262 (16)
H20A	1.0250	−0.4197	0.6907	0.039*
H20B	0.9874	−0.3770	0.7517	0.039*
H20C	1.1112	−0.4923	0.7454	0.039*
N1	0.8788 (6)	0.3370 (5)	0.9937 (2)	0.0136 (11)
N2	1.0102 (6)	0.1260 (5)	0.9339 (2)	0.0158 (11)
N3	1.2599 (6)	−0.2626 (5)	0.7915 (2)	0.0193 (12)
Cl1	0.7217 (2)	0.37547 (19)	0.82157 (8)	0.0343 (5)
Cl2	0.61076 (19)	0.05105 (18)	0.93193 (7)	0.0275 (4)
Hg1	0.77787 (3)	0.23825 (3)	0.905699 (10)	0.01999 (11)
H10C	1.155 (5)	0.115 (8)	1.004 (3)	0.04 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.013 (2)	0.019 (2)	0.026 (3)	−0.0041 (18)	0.014 (2)	0.0005 (19)
C2	0.020 (4)	0.024 (4)	0.022 (4)	−0.006 (3)	−0.002 (3)	−0.001 (3)
C3	0.022 (4)	0.016 (3)	0.039 (4)	−0.007 (3)	0.008 (3)	−0.007 (3)
C4	0.019 (4)	0.024 (4)	0.025 (4)	−0.006 (3)	0.010 (3)	−0.002 (3)
C5	0.034 (4)	0.025 (4)	0.020 (4)	−0.011 (3)	0.000 (3)	−0.004 (3)
C6	0.028 (4)	0.013 (3)	0.025 (4)	−0.006 (3)	0.003 (3)	0.000 (3)
C7	0.021 (4)	0.018 (3)	0.024 (4)	−0.011 (3)	0.005 (3)	0.001 (3)
C8	0.017 (3)	0.028 (4)	0.012 (3)	−0.003 (3)	−0.006 (3)	0.002 (3)
C9	0.019 (4)	0.019 (3)	0.013 (3)	−0.010 (3)	0.001 (3)	0.001 (2)
C10	0.013 (2)	0.019 (2)	0.026 (3)	−0.0041 (18)	0.014 (2)	0.0005 (19)
C11	0.021 (4)	0.007 (3)	0.021 (3)	0.001 (3)	−0.002 (3)	−0.001 (2)
C12	0.024 (4)	0.013 (3)	0.022 (3)	−0.007 (3)	0.001 (3)	0.000 (3)
C13	0.018 (4)	0.014 (3)	0.036 (4)	0.003 (3)	−0.002 (3)	0.004 (3)
C14	0.021 (4)	0.022 (4)	0.017 (3)	−0.005 (3)	0.001 (3)	−0.001 (3)
C15	0.019 (3)	0.013 (3)	0.016 (3)	−0.003 (3)	−0.005 (3)	0.002 (2)
C16	0.020 (3)	0.014 (3)	0.022 (4)	0.005 (3)	−0.001 (3)	0.005 (3)
C17	0.022 (4)	0.015 (3)	0.033 (4)	0.004 (3)	0.003 (3)	−0.003 (3)
C18	0.022 (4)	0.024 (4)	0.054 (5)	0.006 (3)	0.006 (4)	0.008 (3)
C19	0.038 (4)	0.015 (3)	0.027 (4)	0.003 (3)	0.013 (3)	−0.001 (3)
C20	0.031 (4)	0.028 (4)	0.016 (3)	−0.004 (3)	−0.008 (3)	−0.004 (3)
N1	0.014 (3)	0.013 (3)	0.014 (3)	−0.008 (2)	0.002 (2)	−0.001 (2)
N2	0.013 (3)	0.016 (3)	0.018 (3)	0.002 (2)	0.002 (2)	0.002 (2)
N3	0.018 (3)	0.017 (3)	0.025 (3)	0.002 (2)	0.010 (2)	0.000 (2)
Cl1	0.0427 (12)	0.0243 (9)	0.0308 (10)	−0.0061 (8)	−0.0144 (8)	0.0075 (7)
Cl2	0.0202 (9)	0.0320 (9)	0.0285 (9)	−0.0071 (7)	−0.0035 (7)	0.0050 (7)
Hg1	0.01749 (17)	0.02169 (16)	0.02002 (16)	0.00000 (10)	−0.00049 (11)	−0.00019 (10)

Geometric parameters (Å, º) top

Hg1—Cl1	2.3654 (19)	C14—C15	1.410 (9)
Hg1—Cl2	2.4394 (18)	C15—C16	1.383 (9)
Hg1—N1	2.340 (5)	C17—C18	1.499 (10)
Hg1—N2	2.334 (5)	C19—C20	1.527 (10)
N1—C1	1.363 (8)	C2—H2	0.9300
N1—C9	1.335 (8)	C3—H3	0.9300
N2—C10	1.290 (8)	C4—H4	0.9300
N2—C11	1.402 (8)	C5—H5	0.9300
N3—C14	1.358 (8)	C7—H7	0.9300
N3—C17	1.478 (9)	C8—H8	0.9300
N3—C19	1.448 (9)	C10—H10C	0.91 (6)
C1—C2	1.419 (10)	C12—H12	0.9300
C1—C6	1.418 (10)	C13—H13	0.9300
C2—C3	1.372 (10)	C15—H15	0.9300
C3—C4	1.392 (10)	C16—H16	0.9300
C4—C5	1.368 (10)	C17—H17A	0.9700
C5—C6	1.410 (10)	C17—H17B	0.9700
C6—C7	1.397 (10)	C18—H18A	0.9600
C7—C8	1.373 (9)	C18—H18B	0.9600
C8—C9	1.440 (10)	C18—H18C	0.9600
C9—C10	1.464 (9)	C19—H19A	0.9700
C11—C12	1.397 (9)	C19—H19B	0.9700
C11—C16	1.418 (10)	C20—H20A	0.9600
C12—C13	1.362 (9)	C20—H20B	0.9600
C13—C14	1.412 (10)	C20—H20C	0.9600

Cl1—Hg1—Cl2	122.85 (6)	C3—C2—H2	120.00
Cl1—Hg1—N1	122.31 (12)	C2—C3—H3	120.00
Cl1—Hg1—N2	124.75 (13)	C4—C3—H3	120.00
Cl2—Hg1—N1	103.99 (13)	C3—C4—H4	119.00
Cl2—Hg1—N2	97.92 (13)	C5—C4—H4	120.00
N1—Hg1—N2	73.11 (17)	C4—C5—H5	120.00
Hg1—N1—C1	128.9 (4)	C6—C5—H5	120.00
Hg1—N1—C9	111.2 (4)	C6—C7—H7	120.00
C1—N1—C9	119.4 (5)	C8—C7—H7	120.00
Hg1—N2—C10	113.9 (4)	C7—C8—H8	121.00
Hg1—N2—C11	124.4 (4)	C9—C8—H8	120.00
C10—N2—C11	121.5 (5)	N2—C10—H10C	125 (4)
C14—N3—C17	121.5 (5)	C9—C10—H10C	116 (5)
C14—N3—C19	122.6 (6)	C11—C12—H12	119.00
C17—N3—C19	115.9 (5)	C13—C12—H12	119.00
N1—C1—C2	118.9 (6)	C12—C13—H13	119.00
N1—C1—C6	121.9 (6)	C14—C13—H13	119.00
C2—C1—C6	119.1 (6)	C14—C15—H15	119.00
C1—C2—C3	120.4 (6)	C16—C15—H15	119.00
C2—C3—C4	120.1 (6)	C11—C16—H16	119.00
C3—C4—C5	121.0 (6)	C15—C16—H16	119.00
C4—C5—C6	120.7 (6)	N3—C17—H17A	109.00
C1—C6—C5	118.6 (6)	N3—C17—H17B	109.00
C1—C6—C7	118.3 (6)	C18—C17—H17A	109.00
C5—C6—C7	123.0 (6)	C18—C17—H17B	109.00
C6—C7—C8	119.9 (6)	H17A—C17—H17B	108.00
C7—C8—C9	119.1 (6)	C17—C18—H18A	110.00
N1—C9—C8	121.4 (6)	C17—C18—H18B	109.00
N1—C9—C10	120.9 (6)	C17—C18—H18C	109.00
C8—C9—C10	117.7 (6)	H18A—C18—H18B	109.00
N2—C10—C9	119.5 (6)	H18A—C18—H18C	109.00
N2—C11—C12	125.4 (6)	H18B—C18—H18C	109.00
N2—C11—C16	118.4 (6)	N3—C19—H19A	109.00
C12—C11—C16	116.2 (6)	N3—C19—H19B	109.00
C11—C12—C13	122.3 (6)	C20—C19—H19A	109.00
C12—C13—C14	122.2 (7)	C20—C19—H19B	109.00
N3—C14—C13	122.3 (6)	H19A—C19—H19B	108.00
N3—C14—C15	121.5 (6)	C19—C20—H20A	110.00
C13—C14—C15	116.2 (6)	C19—C20—H20B	109.00
C14—C15—C16	121.4 (6)	C19—C20—H20C	109.00
C11—C16—C15	121.7 (6)	H20A—C20—H20B	109.00
N3—C17—C18	114.4 (6)	H20A—C20—H20C	109.00
N3—C19—C20	113.7 (6)	H20B—C20—H20C	109.00
C1—C2—H2	120.00

C6—C1—C2—C3	−0 (1)	N2—C11—C16—C15	−179.8 (6)
N1—C1—C2—C3	−179.0 (6)	C12—C11—N2—C10	−6 (1)
C2—C1—C6—C5	2 (1)	C12—C11—N2—Hg1	178.5 (5)
C2—C1—C6—C7	−179.1 (6)	C16—C11—N2—C10	176.3 (6)
N1—C1—C6—C5	−179.6 (6)	C16—C11—N2—Hg1	1.1 (8)
N1—C1—C6—C7	−0 (1)	C11—C12—C13—C14	−0 (1)
C2—C1—N1—C9	177.2 (6)	C12—C13—C14—C15	1 (1)
C2—C1—N1—Hg1	−12.2 (9)	C12—C13—C14—N3	179.8 (6)
C6—C1—N1—C9	−1.7 (9)	C13—C14—C15—C16	−0 (1)
C6—C1—N1—Hg1	169.0 (5)	N3—C14—C15—C16	−179.0 (6)
C1—C2—C3—C4	−1 (1)	C13—C14—N3—C17	7 (1)
C2—C3—C4—C5	1 (1)	C13—C14—N3—C19	−174.1 (6)
C3—C4—C5—C6	1 (1)	C15—C14—N3—C17	−174.9 (6)
C4—C5—C6—C1	−2 (1)	C15—C14—N3—C19	5 (1)
C4—C5—C6—C7	178.9 (7)	C14—C15—C16—C11	−2 (1)
C1—C6—C7—C8	2 (1)	C18—C17—N3—C14	−86.3 (8)
C5—C6—C7—C8	−178.5 (7)	C18—C17—N3—C19	94.3 (7)
C6—C7—C8—C9	−2 (1)	C20—C19—N3—C14	−86.4 (8)
C7—C8—C9—C10	178.8 (6)	C20—C19—N3—C17	93.1 (7)
C7—C8—C9—N1	0 (1)	C1—N1—Hg1—N2	178.5 (6)
C8—C9—C10—N2	178.7 (6)	C1—N1—Hg1—Cl1	57.6 (5)
N1—C9—C10—N2	−3 (1)	C1—N1—Hg1—Cl2	−87.3 (5)
C8—C9—N1—C1	1.5 (9)	C9—N1—Hg1—N2	−10.3 (4)
C8—C9—N1—Hg1	−170.7 (5)	C9—N1—Hg1—Cl1	−131.1 (4)
C10—C9—N1—C1	−176.8 (6)	C9—N1—Hg1—Cl2	83.9 (4)
C10—C9—N1—Hg1	11.1 (7)	C10—N2—Hg1—N1	9.2 (4)
C9—C10—N2—C11	177.2 (6)	C10—N2—Hg1—Cl1	127.2 (4)
C9—C10—N2—Hg1	−7.1 (8)	C10—N2—Hg1—Cl2	−93.0 (4)
C16—C11—C12—C13	−2 (1)	C11—N2—Hg1—N1	−175.2 (5)
N2—C11—C12—C13	−179.2 (6)	C11—N2—Hg1—Cl1	−57.2 (5)
C12—C11—C16—C15	2 (1)	C11—N2—Hg1—Cl2	82.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cl2ⁱ	0.93	2.82	3.703 (7)	159
C15—H15···Cl1ⁱⁱ	0.93	2.82	3.715 (7)	162

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cl2ⁱ	0.93	2.82	3.703 (7)	159
C15—H15···Cl1ⁱⁱ	0.93	2.82	3.715 (7)	162

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

Acknowledgements

The authors are grateful to the Project of the Department of Science and Technology of India for research grant No. SR/FT/CS-093/2009.

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