Crystal structure of di­chlorido­{N1-phenyl-N4-[(quinolin-2-yl-κN)methylidene]benzene-1,4-diamine-κN4}mercury(II)

Faizi, M.S.H.; Prisyazhnaya, E.V.; Iskenderov, T.S.

doi:10.1107/S2056989015001620

metal-organic compounds

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ISSN: 2056-9890

Volume 71| Part 2| February 2015| Pages m46-m47

doi:10.1107/S2056989015001620

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Crystal structure of dichlorido{N¹-phenyl-N⁴-[(quinolin-2-yl-κN)methylidene]benzene-1,4-diamine-κN⁴}mercury(II)

Md. Serajul Haque Faizi,^a Elena V. Prisyazhnaya ^b ^* and Turganbay S. Iskenderov ^c

^aDepartment of Chemistry, Indian Institute of Technology Kanpur, Kanpur, UP 208 016, India, ^bDepartment of Chemistry, Kyiv National University of Construction and Architecture, Povitroflotsky Avenue 31, 03680 Kiev, Ukraine, and ^cNational Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv, Ukraine
^*Correspondence e-mail: eprisyazhnaya@ukr.net

Edited by M. Weil, Vienna University of Technology, Austria (Received 19 January 2015; accepted 24 January 2015; online 31 January 2015)

In the mononuclear title complex, [HgCl₂(C₂₂H₁₇N₃)], synthesized from the quinoline-derived Schiff base N¹-phenyl-N⁴-[(quinolin-2-yl)methylidene]benzene-1,4-diamine (PQMBD) and HgCl₂, the coordination sphere around the Hg²⁺ atom is distorted tetrahedral, comprising two Cl atoms [Hg—Cl = 2.3487 (14) and 2.4490 (15) Å] and two N atom donors from the PQMBD ligand, viz. the quinolyl and the imine N atom [Hg—N = 2.270 (4) and 2.346 (4) Å, respectively]. The dihedral angle between the two benzene rings attached to the amino group is 43.7 (3)°. In the crystal, N—H⋯Cl and C—H⋯Cl hydrogen bonds, as well as π–π stacking interactions between one phenyl ring and the pyridine ring of the quinoline moiety of an adjacent molecule [centroid-to-centroid separation = 3.617 (4) Å] are observed, resulting in a three-dimensional network.

Keywords: crystal structure; Schiff base; mercury(II) complex; N—H⋯Cl and C—H⋯Cl hydrogen bonding; π–π stacking interactions.

CCDC reference: 1045457

1. Related literature

For the hazards of mercury in organisms, see: Mandal et al. (2012 ). For reports of quinolyl derivatives of Schiff bases, see: Motswainyana et al. (2013 ); Das et al. (2013 ); Song et al. (2011 ); Jursic et al. (2002 ). For background to related Schiff base–metal complexes, see: Faizi & Hussain (2014 ); Faizi et al. (2014 ); Moroz et al. (2012 ). For related Hg-containing structures, see: Marjani et al. (2009 ); Faizi & Sen (2014 ), and for related Schiff base complexes, see: Penkova et al. (2009 $[Penkova, L. V., Maci\,ag, A., Rybak-Akimova, E. V., Haukka, M., Pavlenko, V. A., Iskenderov, T. S., Kozłowski, H., Meyer, F. & Fritsky, I. O. (2009). Inorg. Chem. 48, 6960-6971.]$ , 2010 ); Strotmeyer et al. (2003 ); Petrusenko et al. (1997 ). The amino group of the title compound is separated from the chelating unit which makes this complex a possible precursor for further functionalization, eventually yielding binuclear compounds as reported by Fritsky et al. (1998 , 2006 ) and Kanderal et al. (2005 ).

2. Experimental

2.1. Crystal data

[HgCl₂(C₂₂H₁₇N₃)]
M_r = 594.88
Monoclinic, C 2/c
a = 29.265 (5) Å
b = 7.5671 (13) Å
c = 18.811 (3) Å
β = 99.271 (7)°
V = 4111.4 (12) Å³
Z = 8
Mo Kα radiation
μ = 7.76 mm⁻¹
T = 100 K
0.18 × 0.15 × 0.10 mm

2.2. Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.336, T_max = 0.511
22545 measured reflections
5133 independent reflections
3182 reflections with I > 2σ(I)
R_int = 0.059

2.3. Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.087
S = 1.00
5133 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.99 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯Cl2ⁱ	0.86	2.58	3.363 (4)	151
C10—H10⋯Cl2ⁱⁱ	0.93	2.81	3.679 (7)	157
C20—H20⋯Cl1ⁱⁱⁱ	0.93	2.80	3.692 (11)	160
Symmetry codes: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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, 2015 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2006 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1045457

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015001620/wm5117sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015001620/wm5117Isup2.hkl

checkCIF report

Related literature top

For the hazards of mercury in organisms, see: Mandal et al. (2012). For reports of quinolyl derivatives of Schiff bases, see: Motswainyana et al. (2013); Das et al. (2013); Song et al. (2011); Jursic et al. (2002). For background to related Schiff base–metal complexes, see: Faizi & Hussain (2014); Faizi et al. (2014); Moroz et al. (2012). For related Hg-containing structures, see: Marjani et al. (2009); Faizi & Sen (2014), and for related Schiff base complexes, see: Penkova et al. (2009, 2010); Strotmeyer et al. (2003); Petrusenko et al. (1997). The amino group of the title compound is separated from the chelating unit which makes this complex a possible precursor for further functionalization, eventually yielding binuclear compounds as reported by Fritsky et al. (1998, 2006) and Kanderal et al. (2005).

Experimental top

The iminoquinolyl ligand N¹-phenyl-N⁴-[(quinolin-2-yl)methylidene]benzene-1,4-diamine (PQMBD) was prepared by reacting 2-quinolinecarboxaldehyde (0.085 g, 0.54 mmol) with one equivalent of N-phenyl-p-phenylenediamine (0.100 g, 0.54 mmol) and was obtained in 88% yield (0.15 g). The obtained compound was characterized by FT–IR, NMR and ESI-mass spectroscopy: IR (KBr, ν / cm^-1): 3417, 3052 (C-H arom), 1620 (C═N), 1515, 1313, 843, 756. ¹H NMR (400 MHz, CDCl₃, δ /p.p.m.): 8.85 (1H, S), 8.37 (1H, d), 8.23 (1H, d), 8.16 (1H, d), 7.86 (1H, d), 7.75 (1H, t), 7.58 (1H, t), 7.40 (2H, d), 7.30 (1H, t), 7.13 (5H, m), 6.51 (1H, t). ESI-MS m/z: 324 (M+1).

PQMBD (0.10 g, 0.31 mmol), mercury(II) chloride (0.08 g, 0.31 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, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2006) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2015) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure and the atom-numbering scheme of the title complex, with non-H atoms drawn as displacement ellipsoids at the 40% probability level.
	Fig. 2. N—H···Cl hydrogen bonds between adjacent molecules as viewed along [010].
	Fig. 3. The packing of molecules in the title compound, showing intermolecular interactions as dashed lines.

Dichlorido{N¹-phenyl-N⁴-[(quinolin-2-yl-κN)methylidene]benzene-1,4-diamine-κN⁴}mercury(II) top

Crystal data top

[HgCl₂(C₂₂H₁₇N₃)]	F(000) = 2272
M_r = 594.88	D_x = 1.922 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7479 reflections
a = 29.265 (5) Å	θ = 2.8–24.6°
b = 7.5671 (13) Å	µ = 7.76 mm⁻¹
c = 18.811 (3) Å	T = 100 K
β = 99.271 (7)°	Block, colourless
V = 4111.4 (12) Å³	0.18 × 0.15 × 0.10 mm
Z = 8

Data collection top

Bruker SMART APEX CCD diffractometer	5133 independent reflections
Radiation source: fine-focus sealed tube	3182 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
ω scans	θ_max = 28.4°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −38→38
T_min = 0.336, T_max = 0.511	k = −10→9
22545 measured reflections	l = −25→25

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0374P)² + 1.5818P] where P = (F_o² + 2F_c²)/3
5133 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.99 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

[HgCl₂(C₂₂H₁₇N₃)]	V = 4111.4 (12) Å³
M_r = 594.88	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 29.265 (5) Å	µ = 7.76 mm⁻¹
b = 7.5671 (13) Å	T = 100 K
c = 18.811 (3) Å	0.18 × 0.15 × 0.10 mm
β = 99.271 (7)°

Data collection top

Bruker SMART APEX CCD diffractometer	5133 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	3182 reflections with I > 2σ(I)
T_min = 0.336, T_max = 0.511	R_int = 0.059
22545 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.00	Δρ_max = 0.99 e Å⁻³
5133 reflections	Δρ_min = −0.56 e Å⁻³
253 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
N1	0.42861 (15)	0.2191 (5)	0.5298 (2)	0.0396 (10)
N2	0.50810 (14)	0.2420 (6)	0.4703 (2)	0.0389 (10)
N3	0.65162 (17)	0.3036 (7)	0.3095 (2)	0.0603 (14)
H3A	0.6410	0.3037	0.2641	0.072*
C11	0.54666 (17)	0.2526 (7)	0.4348 (2)	0.0373 (12)
C10	0.50915 (18)	0.2791 (7)	0.5369 (3)	0.0422 (13)
H10	0.5369	0.3144	0.5644	0.051*
C17	0.6984 (2)	0.3274 (7)	0.3265 (3)	0.0507 (14)
C12	0.59004 (18)	0.3146 (7)	0.4656 (2)	0.0431 (13)
H12	0.5952	0.3467	0.5140	0.052*
C1	0.3891 (2)	0.2106 (7)	0.5581 (3)	0.0475 (14)
C16	0.5400 (2)	0.2029 (7)	0.3633 (3)	0.0509 (15)
H16	0.5115	0.1588	0.3418	0.061*
C9	0.46781 (18)	0.2673 (7)	0.5702 (3)	0.0392 (12)
C15	0.5752 (2)	0.2181 (8)	0.3236 (3)	0.0572 (16)
H15	0.5697	0.1861	0.2753	0.069*
C13	0.62510 (18)	0.3293 (7)	0.4263 (3)	0.0447 (13)
H13	0.6537	0.3729	0.4481	0.054*
C6	0.3892 (2)	0.2468 (8)	0.6324 (3)	0.0479 (14)
C7	0.4309 (2)	0.2985 (7)	0.6737 (3)	0.0543 (15)
H7	0.4319	0.3271	0.7220	0.065*
C8	0.4699 (2)	0.3076 (8)	0.6443 (3)	0.0559 (16)
H8	0.4978	0.3400	0.6722	0.067*
C14	0.61872 (19)	0.2795 (7)	0.3533 (3)	0.0469 (14)
Hg1	0.432753 (8)	0.18401 (3)	0.411137 (10)	0.05198 (10)
Cl2	0.40186 (6)	0.4552 (2)	0.35050 (7)	0.0702 (5)
Cl1	0.41693 (5)	−0.0647 (2)	0.33652 (7)	0.0593 (4)
C2	0.3473 (2)	0.1623 (7)	0.5149 (3)	0.0553 (15)
H2	0.3471	0.1343	0.4667	0.066*
C4	0.3076 (2)	0.1986 (8)	0.6148 (4)	0.0699 (19)
H4	0.2798	0.1988	0.6327	0.084*
C3	0.3070 (2)	0.1557 (8)	0.5420 (3)	0.0656 (18)
H3	0.2795	0.1233	0.5129	0.079*
C5	0.3471 (2)	0.2397 (9)	0.6601 (3)	0.0624 (17)
H5	0.3465	0.2628	0.7085	0.075*
C18	0.7240 (2)	0.2570 (9)	0.3877 (3)	0.0632 (17)
H18	0.7096	0.1968	0.4210	0.076*
C19	0.7715 (3)	0.2770 (13)	0.3989 (4)	0.098 (3)
H19	0.7890	0.2272	0.4396	0.118*
C22	0.7218 (3)	0.4179 (9)	0.2794 (3)	0.0700 (19)
H22	0.7050	0.4696	0.2384	0.084*
C21	0.7680 (3)	0.4324 (11)	0.2915 (5)	0.091 (3)
H21	0.7826	0.4886	0.2573	0.110*
C20	0.7937 (3)	0.3686 (15)	0.3512 (5)	0.115 (4)
H20	0.8256	0.3856	0.3602	0.138*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.046 (3)	0.040 (3)	0.033 (2)	0.002 (2)	0.0060 (19)	0.0038 (18)
N2	0.043 (3)	0.040 (2)	0.033 (2)	−0.003 (2)	0.0032 (18)	−0.0005 (18)
N3	0.050 (3)	0.101 (4)	0.030 (2)	0.000 (3)	0.007 (2)	0.001 (2)
C11	0.039 (3)	0.041 (3)	0.034 (3)	0.001 (2)	0.011 (2)	−0.006 (2)
C10	0.045 (3)	0.044 (3)	0.034 (3)	0.003 (2)	−0.002 (2)	0.007 (2)
C17	0.053 (4)	0.056 (4)	0.046 (3)	0.003 (3)	0.015 (3)	−0.004 (3)
C12	0.050 (3)	0.050 (3)	0.029 (2)	−0.002 (3)	0.003 (2)	−0.002 (2)
C1	0.055 (4)	0.040 (3)	0.047 (3)	0.009 (3)	0.008 (3)	0.008 (2)
C16	0.048 (3)	0.064 (4)	0.039 (3)	−0.007 (3)	0.000 (2)	−0.014 (3)
C9	0.048 (3)	0.038 (3)	0.033 (3)	0.007 (2)	0.007 (2)	0.000 (2)
C15	0.055 (4)	0.085 (5)	0.030 (3)	−0.009 (3)	0.002 (3)	−0.013 (3)
C13	0.037 (3)	0.058 (4)	0.037 (3)	−0.005 (3)	0.000 (2)	−0.007 (3)
C6	0.057 (4)	0.048 (3)	0.042 (3)	0.006 (3)	0.015 (3)	0.009 (3)
C7	0.070 (4)	0.061 (4)	0.034 (3)	0.002 (3)	0.015 (3)	−0.003 (3)
C8	0.060 (4)	0.071 (4)	0.034 (3)	−0.001 (3)	0.000 (3)	0.003 (3)
C14	0.046 (3)	0.058 (4)	0.037 (3)	0.005 (3)	0.007 (2)	0.000 (3)
Hg1	0.05736 (16)	0.05833 (16)	0.03782 (13)	−0.00317 (12)	0.00037 (9)	−0.00853 (11)
Cl2	0.1027 (13)	0.0504 (9)	0.0476 (8)	0.0032 (9)	−0.0178 (8)	−0.0030 (7)
Cl1	0.0732 (10)	0.0508 (9)	0.0524 (8)	−0.0083 (8)	0.0053 (7)	−0.0122 (7)
C2	0.052 (4)	0.064 (4)	0.052 (3)	−0.002 (3)	0.012 (3)	0.000 (3)
C4	0.066 (4)	0.078 (5)	0.073 (5)	0.007 (4)	0.032 (4)	−0.001 (4)
C3	0.049 (4)	0.078 (5)	0.070 (4)	0.003 (3)	0.011 (3)	0.007 (4)
C5	0.069 (5)	0.068 (4)	0.058 (4)	0.009 (4)	0.034 (4)	0.010 (3)
C18	0.051 (4)	0.087 (5)	0.052 (4)	0.003 (4)	0.010 (3)	0.009 (3)
C19	0.057 (5)	0.174 (9)	0.062 (4)	0.006 (5)	0.006 (4)	−0.022 (5)
C22	0.082 (5)	0.076 (5)	0.061 (4)	0.009 (4)	0.040 (4)	0.008 (4)
C21	0.094 (6)	0.097 (6)	0.098 (6)	−0.031 (5)	0.061 (5)	−0.025 (5)
C20	0.069 (6)	0.179 (10)	0.107 (7)	−0.036 (6)	0.045 (5)	−0.069 (7)

Geometric parameters (Å, º) top

N1—C9	1.322 (6)	C13—H13	0.9300
N1—C1	1.349 (7)	C6—C7	1.394 (8)
N1—Hg1	2.270 (4)	C6—C5	1.413 (8)
N2—C10	1.279 (6)	C7—C8	1.347 (8)
N2—C11	1.402 (6)	C7—H7	0.9300
N2—Hg1	2.346 (4)	C8—H8	0.9300
N3—C17	1.367 (7)	Hg1—Cl1	2.3487 (14)
N3—C14	1.377 (7)	Hg1—Cl2	2.4490 (15)
N3—H3A	0.8600	C2—C3	1.359 (8)
C11—C16	1.380 (6)	C2—H2	0.9300
C11—C12	1.389 (7)	C4—C5	1.358 (9)
C10—C9	1.453 (7)	C4—C3	1.403 (8)
C10—H10	0.9300	C4—H4	0.9300
C17—C22	1.385 (8)	C3—H3	0.9300
C17—C18	1.375 (8)	C5—H5	0.9300
C12—C13	1.362 (7)	C18—C19	1.381 (9)
C12—H12	0.9300	C18—H18	0.9300
C1—C2	1.404 (8)	C19—C20	1.375 (12)
C1—C6	1.425 (7)	C19—H19	0.9300
C16—C15	1.370 (8)	C22—C21	1.340 (9)
C16—H16	0.9300	C22—H22	0.9300
C9—C8	1.418 (7)	C21—C20	1.338 (11)
C15—C14	1.385 (7)	C21—H21	0.9300
C15—H15	0.9300	C20—H20	0.9300
C13—C14	1.409 (7)

C9—N1—C1	120.4 (4)	C6—C7—H7	119.7
C9—N1—Hg1	114.8 (3)	C7—C8—C9	119.1 (5)
C1—N1—Hg1	124.5 (4)	C7—C8—H8	120.4
C10—N2—C11	124.0 (4)	C9—C8—H8	120.4
C10—N2—Hg1	112.2 (3)	C15—C14—N3	119.3 (5)
C11—N2—Hg1	123.5 (3)	C15—C14—C13	116.8 (5)
C17—N3—C14	130.3 (5)	N3—C14—C13	123.6 (5)
C17—N3—H3A	114.8	N1—Hg1—N2	72.96 (15)
C14—N3—H3A	114.8	N1—Hg1—Cl1	130.14 (11)
C16—C11—C12	118.3 (5)	N2—Hg1—Cl1	120.86 (11)
C16—C11—N2	116.8 (5)	N1—Hg1—Cl2	106.60 (11)
C12—C11—N2	124.9 (4)	N2—Hg1—Cl2	108.21 (11)
N2—C10—C9	121.3 (5)	Cl1—Hg1—Cl2	111.75 (5)
N2—C10—H10	119.4	C3—C2—C1	121.4 (6)
C9—C10—H10	119.4	C3—C2—H2	119.3
N3—C17—C22	119.6 (5)	C1—C2—H2	119.3
N3—C17—C18	122.4 (5)	C5—C4—C3	122.7 (6)
C22—C17—C18	118.0 (6)	C5—C4—H4	118.7
C13—C12—C11	121.2 (4)	C3—C4—H4	118.7
C13—C12—H12	119.4	C2—C3—C4	118.9 (6)
C11—C12—H12	119.4	C2—C3—H3	120.6
N1—C1—C2	120.5 (5)	C4—C3—H3	120.6
N1—C1—C6	120.8 (5)	C4—C5—C6	118.8 (6)
C2—C1—C6	118.7 (5)	C4—C5—H5	120.6
C15—C16—C11	120.5 (5)	C6—C5—H5	120.6
C15—C16—H16	119.7	C19—C18—C17	119.0 (6)
C11—C16—H16	119.7	C19—C18—H18	120.5
N1—C9—C8	121.4 (5)	C17—C18—H18	120.5
N1—C9—C10	118.3 (4)	C18—C19—C20	121.7 (8)
C8—C9—C10	120.3 (5)	C18—C19—H19	119.2
C16—C15—C14	122.1 (5)	C20—C19—H19	119.2
C16—C15—H15	118.9	C21—C22—C17	121.4 (7)
C14—C15—H15	118.9	C21—C22—H22	119.3
C12—C13—C14	121.0 (5)	C17—C22—H22	119.3
C12—C13—H13	119.5	C22—C21—C20	121.9 (7)
C14—C13—H13	119.5	C22—C21—H21	119.0
C7—C6—C5	122.9 (5)	C20—C21—H21	119.0
C7—C6—C1	117.6 (5)	C21—C20—C19	118.0 (8)
C5—C6—C1	119.4 (6)	C21—C20—H20	121.0
C8—C7—C6	120.6 (5)	C19—C20—H20	121.0
C8—C7—H7	119.7

C10—N2—C11—C16	178.2 (5)	C16—C15—C14—N3	−175.4 (6)
Hg1—N2—C11—C16	−8.8 (7)	C16—C15—C14—C13	−1.1 (9)
C10—N2—C11—C12	−4.2 (8)	C17—N3—C14—C15	−165.2 (6)
Hg1—N2—C11—C12	168.9 (4)	C17—N3—C14—C13	20.9 (10)
C11—N2—C10—C9	179.3 (5)	C12—C13—C14—C15	0.9 (8)
Hg1—N2—C10—C9	5.6 (6)	C12—C13—C14—N3	174.9 (5)
C14—N3—C17—C22	−153.7 (6)	C9—N1—Hg1—N2	5.3 (3)
C14—N3—C17—C18	29.6 (10)	C1—N1—Hg1—N2	178.8 (4)
C16—C11—C12—C13	1.1 (8)	C9—N1—Hg1—Cl1	121.6 (3)
N2—C11—C12—C13	−176.5 (5)	C1—N1—Hg1—Cl1	−64.9 (4)
C9—N1—C1—C2	178.9 (5)	C9—N1—Hg1—Cl2	−99.2 (3)
Hg1—N1—C1—C2	5.8 (7)	C1—N1—Hg1—Cl2	74.3 (4)
C9—N1—C1—C6	−2.3 (8)	C10—N2—Hg1—N1	−5.6 (3)
Hg1—N1—C1—C6	−175.5 (4)	C11—N2—Hg1—N1	−179.4 (4)
C12—C11—C16—C15	−1.3 (8)	C10—N2—Hg1—Cl1	−132.7 (3)
N2—C11—C16—C15	176.6 (5)	C11—N2—Hg1—Cl1	53.5 (4)
C1—N1—C9—C8	1.3 (7)	C10—N2—Hg1—Cl2	96.7 (4)
Hg1—N1—C9—C8	175.1 (4)	C11—N2—Hg1—Cl2	−77.1 (4)
C1—N1—C9—C10	−178.3 (5)	N1—C1—C2—C3	−178.9 (5)
Hg1—N1—C9—C10	−4.6 (6)	C6—C1—C2—C3	2.3 (8)
N2—C10—C9—N1	−0.9 (8)	C1—C2—C3—C4	0.1 (9)
N2—C10—C9—C8	179.5 (5)	C5—C4—C3—C2	−2.7 (10)
C11—C16—C15—C14	1.3 (10)	C3—C4—C5—C6	2.7 (10)
C11—C12—C13—C14	−1.0 (8)	C7—C6—C5—C4	175.9 (6)
N1—C1—C6—C7	2.8 (8)	C1—C6—C5—C4	−0.1 (9)
C2—C1—C6—C7	−178.5 (5)	N3—C17—C18—C19	175.8 (6)
N1—C1—C6—C5	178.9 (5)	C22—C17—C18—C19	−0.9 (10)
C2—C1—C6—C5	−2.3 (8)	C17—C18—C19—C20	1.4 (12)
C5—C6—C7—C8	−178.2 (6)	N3—C17—C22—C21	−174.9 (6)
C1—C6—C7—C8	−2.2 (9)	C18—C17—C22—C21	1.9 (10)
C6—C7—C8—C9	1.3 (9)	C17—C22—C21—C20	−3.5 (13)
N1—C9—C8—C7	−0.8 (8)	C22—C21—C20—C19	3.8 (14)
C10—C9—C8—C7	178.9 (5)	C18—C19—C20—C21	−2.8 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···Cl2ⁱ	0.86	2.58	3.363 (4)	151
C10—H10···Cl2ⁱⁱ	0.93	2.81	3.679 (7)	157
C20—H20···Cl1ⁱⁱⁱ	0.93	2.80	3.692 (11)	160

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···Cl2ⁱ	0.86	2.58	3.363 (4)	151
C10—H10···Cl2ⁱⁱ	0.93	2.81	3.679 (7)	156.7
C20—H20···Cl1ⁱⁱⁱ	0.93	2.80	3.692 (11)	160.0

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

Acknowledgements

The authors are grateful to the Department of Chemistry, IIT Kanpur, Kanpur 208 016, India, for the X-ray data collection.

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