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

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.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.038
• wR factor = 0.087
• Data-to-parameter ratio = 20.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent  C     Ueq(max)/Ueq(min) Range        3.1 Ratio
PLAT234_ALERT_4_C Large Hirshfeld Difference C20    --  C21     ..       0.16 Ang.
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....        C20 Check
PLAT331_ALERT_2_C Small Average Phenyl   C-C Dist. C17    -C22           1.37 Ang.
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0088 Ang.

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Hg1    --  Cl2     ..       11.3 su
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          3 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         16 Note

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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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, 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).

S1. Experimental

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.

S2. Refinement

The N-bound H-atom was located in a difference Fourier maps, and the positions restrained to N—H = 0.86 Å and U_iso(H) = 1.2U_eq(N). All other H-atoms were positioned geometrically and refined using a riding model with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C).

Computing details

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

	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)

Crystal data

[HgCl2(C22H17N3)]	F(000) = 2272
Mr = 594.88	Dx = 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) Å^3	0.18 × 0.15 × 0.10 mm
Z = 8

Data collection

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

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0374P)^2 + 1.5818P] where P = (Fo^2 + 2Fc^2)/3
5133 reflections	(Δ/σ)max = 0.001
253 parameters	Δρmax = 0.99 e Å^−3
0 restraints	Δρmin = −0.56 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···Cl2^i	0.86	2.58	3.363 (4)	151
C10—H10···Cl2^ii	0.93	2.81	3.679 (7)	157
C20—H20···Cl1^iii	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.