Two new zinc(II) and mercury(II) com­plexes based on N,N′-(cyclo­hexane-1,2-diyl­idene)bis­(4-fluoro­benzo­hydrazide): synthesis, crystal structures and antibacterial activities

Reaction of N,N′-(cyclo­hexane-1,2-diyl­idene)bis­(4-fluoro­benzo­hydrazide), C₂₀H₁₈F₂N₄O₂, (L^F), with zinc chloride and mercury(II) chloride produced different types and shapes of neutral coordination com­plexes, namely, di­chlorido­[N,N′-(cyclo­hexane-1,2-diyl­idene)bis­(4-fluoro­benzo­hydrazide)-κ²N,O]zinc(II), [ZnCl₂(C₂₀H₁₈F₂N₄O₂)], (1), and di­chlorido­[N,N′-(cyclo­hexane-1,2-diyl­idene)bis­(4-fluoro­benzo­hydrazide)-κ⁴O,N,N′,O′]mercury(II), [HgCl₂(C₂₀H₁₈F₂N₄O₂)], (2). The organic ligand and its metal com­plexes are char­acterized using various techniques: IR, UV–Vis and nuclear magnetic resonance (NMR) spectroscopies, in addition to powder X-ray diffraction (PXRD), single-crystal X-ray crystallography and microelemental analysis. Depending upon the data from these analyses and measurements, a typical tetra­hedral geometry was confirmed for zinc com­plex (1), in which the Zn^II atom is located outside the bis­(benz­hydrazone) core. The Hg^II atom in (2) is found within the core and has a common octa­hedral structure. The in vitro anti­bacterial activities of the prepared com­pounds were evaluated against two different bacterial strains, i.e. gram positive Bacillus subtilis and gram negative Pseudomonas aeruginosa bacteria. The prepared com­pounds exhibited differentiated growth-inhibitory activities against these two bacterial strains based on the difference in their lipophilic nature and structural features.

Computing details

For all structures, data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).

N,N'-(Cyclohexane-1,2-diylidene)bis(4-fluorobenzohydrazide) methanol monosolvate (shelx)

Crystal data

C20H18F2N4O2·CH4O	Dx = 1.367 Mg m^−3
Mr = 416.42	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 13218 reflections
a = 7.5679 (3) Å	θ = 1.8–31.0°
b = 15.2500 (7) Å	µ = 0.11 mm^−1
c = 17.5264 (7) Å	T = 296 K
V = 2022.73 (15) Å^3	Prism, yellow
Z = 4	0.79 × 0.55 × 0.38 mm
F(000) = 872

Data collection

Stoe IPDS 2 diffractometer	6161 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3553 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.042
Detector resolution: 6.67 pixels mm^-1	θmax = 30.6°, θmin = 1.8°
rotation method scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −21→21
Tmin = 0.926, Tmax = 0.962	l = −24→23
15870 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[σ^2(Fo^2) + (0.0509P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.111	(Δ/σ)max < 0.001
S = 0.96	Δρmax = 0.13 e Å^−3
6161 reflections	Δρmin = −0.11 e Å^−3
284 parameters	Absolute structure: Flack x determined using 1095 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.3 (5)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. STOE diffractometer equipped with an IPDS II image plate detector was used to collect the crystal data of L^F, 1 and 2. The collection was carried out at room temperature (296K) using graphite monochromated Mo Kα radiation (λ=0.71073Å) inω-scanning mode. SHELXS-97(Sheldrick, 1997)was used to solve (direct methods) and refine (full-matrix least-squares method) the structures, implemented in the WinGX (Farrugia, 1999)program suite.

Data collection: X-AREA and data reduction: X-RED32 (Cie, 2002). All non-hydrogen atoms were assigned anisotropic thermal parameters. Experimental details of the crystal data, data collection and refinement are illustrated inTable 1. The structure analysis and presentation of the results were done by the general-purpose crystallographic tool PLATON(Spek, 2009), while themolecular graphics were made by ORTEP-3 for Windows(Farrugia, 1997).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F1	0.4528 (3)	1.10675 (12)	0.60787 (11)	0.1035 (7)
F2	0.2132 (3)	0.39921 (15)	0.70516 (9)	0.0940 (6)
O1	0.5341 (4)	0.70430 (13)	0.53813 (10)	0.0830 (7)
O2	0.4777 (4)	0.36341 (13)	0.36771 (10)	0.0892 (8)
O3	0.5958 (3)	0.37338 (14)	0.20009 (11)	0.0703 (6)
C21	0.7497 (6)	0.3294 (3)	0.2170 (2)	0.0987 (12)
H21A	0.827747	0.367562	0.244577	0.148*
H21B	0.805659	0.310958	0.170523	0.148*
H21C	0.723055	0.278930	0.247671	0.148*
N2	0.5744 (3)	0.67763 (13)	0.38715 (11)	0.0534 (5)
N3	0.5911 (3)	0.51341 (12)	0.30988 (10)	0.0498 (5)
N4	0.5234 (3)	0.50838 (14)	0.38164 (11)	0.0506 (5)
N1	0.5658 (3)	0.75956 (15)	0.41977 (12)	0.0583 (6)
C4	0.5121 (3)	0.85858 (16)	0.52371 (12)	0.0513 (6)
C13	0.6506 (3)	0.58657 (16)	0.28352 (12)	0.0492 (5)
C7	0.5350 (4)	0.76724 (16)	0.49571 (14)	0.0551 (6)
C20	0.4054 (4)	0.49610 (18)	0.53713 (14)	0.0596 (7)
H20	0.451810	0.549547	0.521260	0.071*
C15	0.4015 (3)	0.42542 (17)	0.48752 (13)	0.0523 (6)
C14	0.4700 (4)	0.42869 (17)	0.40741 (13)	0.0556 (6)
C12	0.7263 (4)	0.57862 (19)	0.20362 (15)	0.0668 (7)
H12A	0.838595	0.548106	0.206539	0.080*
H12B	0.647050	0.543028	0.173088	0.080*
C3	0.4258 (4)	0.92197 (18)	0.48190 (14)	0.0595 (6)
H3	0.380437	0.908133	0.434073	0.071*
C8	0.6539 (3)	0.67224 (16)	0.32176 (13)	0.0497 (5)
C1	0.4732 (4)	1.02404 (19)	0.58029 (16)	0.0663 (8)
C19	0.3397 (4)	0.48679 (19)	0.61068 (15)	0.0654 (7)
H19	0.341261	0.533756	0.644520	0.078*
C6	0.5574 (4)	0.9638 (2)	0.62366 (15)	0.0704 (8)
H6	0.601161	0.978450	0.671570	0.085*
C11	0.7544 (4)	0.66483 (18)	0.16377 (14)	0.0637 (7)
H11A	0.819733	0.655622	0.116840	0.076*
H11B	0.641152	0.690762	0.150970	0.076*
C5	0.5766 (4)	0.88046 (19)	0.59531 (14)	0.0647 (7)
H5	0.633697	0.838109	0.624468	0.078*
C16	0.3321 (4)	0.34702 (19)	0.51202 (15)	0.0649 (7)
H16	0.329343	0.299550	0.478728	0.078*
C10	0.8552 (4)	0.7251 (2)	0.21512 (16)	0.0691 (8)
H10A	0.885119	0.778288	0.187610	0.083*
H10B	0.964379	0.697093	0.230779	0.083*
C9	0.7468 (4)	0.74831 (17)	0.28522 (15)	0.0630 (7)
H9A	0.824373	0.774966	0.322699	0.076*
H9B	0.659324	0.791780	0.270923	0.076*
C17	0.2660 (4)	0.3372 (2)	0.58539 (16)	0.0702 (8)
H17	0.218584	0.284189	0.601711	0.084*
C18	0.2729 (4)	0.4077 (2)	0.63241 (14)	0.0653 (7)
C2	0.4060 (4)	1.00577 (18)	0.51028 (16)	0.0682 (7)
H2	0.347961	1.048702	0.482120	0.082*
H4	0.515 (4)	0.5565 (19)	0.4053 (15)	0.059 (8)*
H1	0.569 (4)	0.803 (2)	0.3933 (19)	0.080 (10)*
H3A	0.574 (6)	0.406 (3)	0.234 (2)	0.122 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.1378 (18)	0.0714 (12)	0.1011 (13)	−0.0034 (12)	0.0141 (13)	−0.0412 (10)
F2	0.1037 (13)	0.1268 (16)	0.0516 (9)	0.0061 (12)	0.0230 (9)	0.0144 (10)
O1	0.145 (2)	0.0554 (12)	0.0489 (10)	0.0052 (13)	−0.0005 (12)	0.0060 (8)
O2	0.152 (2)	0.0567 (12)	0.0592 (11)	−0.0272 (13)	0.0288 (13)	−0.0102 (9)
O3	0.0958 (16)	0.0657 (13)	0.0496 (10)	−0.0005 (11)	−0.0034 (10)	−0.0111 (9)
C21	0.123 (3)	0.098 (3)	0.075 (2)	0.037 (2)	−0.008 (2)	−0.012 (2)
N2	0.0699 (13)	0.0449 (11)	0.0453 (10)	0.0021 (10)	0.0058 (10)	−0.0019 (8)
N3	0.0611 (12)	0.0501 (12)	0.0382 (9)	0.0015 (10)	0.0037 (9)	−0.0019 (8)
N4	0.0652 (13)	0.0467 (12)	0.0400 (10)	−0.0027 (10)	0.0052 (9)	0.0000 (9)
N1	0.0874 (17)	0.0443 (12)	0.0432 (11)	0.0002 (11)	0.0114 (11)	−0.0013 (9)
C4	0.0609 (15)	0.0526 (14)	0.0404 (11)	−0.0041 (12)	0.0061 (11)	−0.0019 (10)
C13	0.0560 (13)	0.0495 (14)	0.0421 (12)	0.0025 (11)	0.0036 (10)	0.0018 (10)
C7	0.0673 (16)	0.0516 (14)	0.0463 (12)	−0.0006 (12)	0.0034 (12)	0.0002 (11)
C20	0.0742 (17)	0.0567 (16)	0.0478 (12)	0.0009 (13)	−0.0008 (12)	0.0043 (11)
C15	0.0595 (14)	0.0529 (14)	0.0444 (11)	−0.0034 (12)	−0.0008 (10)	0.0048 (11)
C14	0.0707 (16)	0.0510 (14)	0.0452 (11)	−0.0058 (13)	0.0025 (11)	−0.0006 (11)
C12	0.0879 (19)	0.0629 (17)	0.0496 (13)	−0.0047 (15)	0.0183 (13)	−0.0026 (13)
C3	0.0724 (17)	0.0608 (16)	0.0454 (12)	0.0029 (15)	−0.0033 (12)	−0.0085 (12)
C8	0.0557 (13)	0.0491 (13)	0.0443 (12)	0.0010 (11)	0.0041 (10)	0.0032 (10)
C1	0.0765 (19)	0.0568 (16)	0.0654 (16)	−0.0066 (14)	0.0147 (15)	−0.0202 (13)
C19	0.0798 (18)	0.0705 (18)	0.0458 (13)	0.0121 (15)	0.0026 (13)	−0.0028 (12)
C6	0.085 (2)	0.082 (2)	0.0444 (13)	−0.0116 (17)	0.0011 (14)	−0.0180 (13)
C11	0.0787 (19)	0.0659 (18)	0.0464 (13)	−0.0048 (14)	0.0112 (12)	0.0069 (12)
C5	0.0823 (19)	0.0667 (17)	0.0451 (13)	−0.0034 (14)	−0.0003 (13)	0.0010 (12)
C16	0.0820 (19)	0.0598 (16)	0.0530 (14)	−0.0093 (15)	0.0041 (14)	0.0031 (12)
C10	0.0786 (18)	0.0662 (17)	0.0624 (16)	−0.0108 (15)	0.0191 (15)	0.0069 (14)
C9	0.0788 (18)	0.0500 (15)	0.0604 (15)	−0.0069 (13)	0.0175 (14)	−0.0002 (12)
C17	0.078 (2)	0.074 (2)	0.0587 (15)	−0.0124 (16)	0.0044 (14)	0.0173 (15)
C18	0.0642 (17)	0.087 (2)	0.0452 (13)	0.0074 (15)	0.0093 (12)	0.0149 (14)
C2	0.0851 (19)	0.0600 (17)	0.0594 (15)	0.0106 (15)	0.0028 (15)	−0.0081 (13)

Geometric parameters (Å, º)

F1—C1	1.360 (3)	C12—C11	1.504 (4)
F2—C18	1.359 (3)	C12—H12A	0.9700
O1—C7	1.214 (3)	C12—H12B	0.9700
O2—C14	1.216 (3)	C3—C2	1.379 (4)
O3—C21	1.377 (4)	C3—H3	0.9300
O3—H3A	0.79 (4)	C8—C9	1.500 (3)
C21—H21A	0.9600	C1—C6	1.352 (4)
C21—H21B	0.9600	C1—C2	1.357 (4)
C21—H21C	0.9600	C19—C18	1.362 (4)
N2—C8	1.297 (3)	C19—H19	0.9300
N2—N1	1.376 (3)	C6—C5	1.372 (4)
N3—C13	1.289 (3)	C6—H6	0.9300
N3—N4	1.360 (3)	C11—C10	1.496 (4)
N4—C14	1.358 (3)	C11—H11A	0.9700
N4—H4	0.85 (3)	C11—H11B	0.9700
N1—C7	1.356 (3)	C5—H5	0.9300
N1—H1	0.81 (3)	C16—C17	1.388 (4)
C4—C3	1.378 (4)	C16—H16	0.9300
C4—C5	1.387 (3)	C10—C9	1.519 (4)
C4—C7	1.487 (3)	C10—H10A	0.9700
C13—C8	1.469 (3)	C10—H10B	0.9700
C13—C12	1.518 (3)	C9—H9A	0.9700
C20—C15	1.385 (4)	C9—H9B	0.9700
C20—C19	1.389 (4)	C17—C18	1.355 (4)
C20—H20	0.9300	C17—H17	0.9300
C15—C16	1.375 (4)	C2—H2	0.9300
C15—C14	1.498 (3)
C21—O3—H3A	109 (3)	C13—C8—C9	120.1 (2)
O3—C21—H21A	109.5	C6—C1—C2	123.1 (3)
O3—C21—H21B	109.5	C6—C1—F1	119.0 (3)
H21A—C21—H21B	109.5	C2—C1—F1	118.0 (3)
O3—C21—H21C	109.5	C18—C19—C20	118.9 (3)
H21A—C21—H21C	109.5	C18—C19—H19	120.6
H21B—C21—H21C	109.5	C20—C19—H19	120.6
C8—N2—N1	116.5 (2)	C1—C6—C5	118.4 (2)
C13—N3—N4	120.80 (19)	C1—C6—H6	120.8
C14—N4—N3	118.0 (2)	C5—C6—H6	120.8
C14—N4—H4	126.3 (18)	C10—C11—C12	109.3 (2)
N3—N4—H4	115.7 (18)	C10—C11—H11A	109.8
C7—N1—N2	119.6 (2)	C12—C11—H11A	109.8
C7—N1—H1	120 (2)	C10—C11—H11B	109.8
N2—N1—H1	120 (2)	C12—C11—H11B	109.8
C3—C4—C5	118.6 (2)	H11A—C11—H11B	108.3
C3—C4—C7	122.5 (2)	C6—C5—C4	120.9 (3)
C5—C4—C7	118.9 (2)	C6—C5—H5	119.6
N3—C13—C8	127.8 (2)	C4—C5—H5	119.6
N3—C13—C12	113.2 (2)	C15—C16—C17	121.4 (3)
C8—C13—C12	119.1 (2)	C15—C16—H16	119.3
O1—C7—N1	122.3 (2)	C17—C16—H16	119.3
O1—C7—C4	122.5 (2)	C11—C10—C9	110.8 (2)
N1—C7—C4	115.1 (2)	C11—C10—H10A	109.5
C15—C20—C19	119.7 (2)	C9—C10—H10A	109.5
C15—C20—H20	120.2	C11—C10—H10B	109.5
C19—C20—H20	120.2	C9—C10—H10B	109.5
C16—C15—C20	119.3 (2)	H10A—C10—H10B	108.1
C16—C15—C14	117.0 (2)	C8—C9—C10	114.7 (2)
C20—C15—C14	123.7 (2)	C8—C9—H9A	108.6
O2—C14—N4	121.9 (2)	C10—C9—H9A	108.6
O2—C14—C15	121.7 (2)	C8—C9—H9B	108.6
N4—C14—C15	116.4 (2)	C10—C9—H9B	108.6
C11—C12—C13	114.3 (2)	H9A—C9—H9B	107.6
C11—C12—H12A	108.7	C18—C17—C16	117.7 (3)
C13—C12—H12A	108.7	C18—C17—H17	121.2
C11—C12—H12B	108.7	C16—C17—H17	121.2
C13—C12—H12B	108.7	C17—C18—F2	118.8 (3)
H12A—C12—H12B	107.6	C17—C18—C19	123.1 (2)
C4—C3—C2	120.6 (2)	F2—C18—C19	118.0 (3)
C4—C3—H3	119.7	C1—C2—C3	118.4 (3)
C2—C3—H3	119.7	C1—C2—H2	120.8
N2—C8—C13	116.9 (2)	C3—C2—H2	120.8
N2—C8—C9	123.1 (2)
C13—N3—N4—C14	−177.1 (2)	C12—C13—C8—N2	174.3 (2)
C8—N2—N1—C7	−160.1 (2)	N3—C13—C8—C9	173.3 (2)
N4—N3—C13—C8	−1.2 (4)	C12—C13—C8—C9	−6.0 (4)
N4—N3—C13—C12	178.1 (2)	C15—C20—C19—C18	0.2 (4)
N2—N1—C7—O1	8.5 (4)	C2—C1—C6—C5	0.4 (5)
N2—N1—C7—C4	−174.7 (2)	F1—C1—C6—C5	179.8 (3)
C3—C4—C7—O1	−145.9 (3)	C13—C12—C11—C10	50.5 (3)
C5—C4—C7—O1	32.6 (4)	C1—C6—C5—C4	0.3 (4)
C3—C4—C7—N1	37.3 (4)	C3—C4—C5—C6	−0.9 (4)
C5—C4—C7—N1	−144.2 (3)	C7—C4—C5—C6	−179.5 (3)
C19—C20—C15—C16	0.1 (4)	C20—C15—C16—C17	0.0 (4)
C19—C20—C15—C14	−179.6 (3)	C14—C15—C16—C17	179.7 (3)
N3—N4—C14—O2	−1.7 (4)	C12—C11—C10—C9	−65.6 (3)
N3—N4—C14—C15	178.2 (2)	N2—C8—C9—C10	171.0 (3)
C16—C15—C14—O2	−5.9 (4)	C13—C8—C9—C10	−8.8 (4)
C20—C15—C14—O2	173.8 (3)	C11—C10—C9—C8	44.5 (3)
C16—C15—C14—N4	174.2 (2)	C15—C16—C17—C18	−0.3 (5)
C20—C15—C14—N4	−6.0 (4)	C16—C17—C18—F2	−178.3 (3)
N3—C13—C12—C11	165.4 (2)	C16—C17—C18—C19	0.6 (5)
C8—C13—C12—C11	−15.3 (4)	C20—C19—C18—C17	−0.5 (5)
C5—C4—C3—C2	0.8 (4)	C20—C19—C18—F2	178.4 (3)
C7—C4—C3—C2	179.4 (3)	C6—C1—C2—C3	−0.5 (5)
N1—N2—C8—C13	−175.0 (2)	F1—C1—C2—C3	−179.9 (3)
N1—N2—C8—C9	5.2 (4)	C4—C3—C2—C1	−0.1 (4)
N3—C13—C8—N2	−6.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N2	0.85 (3)	1.93 (3)	2.611 (3)	137 (2)
O3—H3A···N3	0.79 (4)	2.11 (4)	2.875 (3)	161 (4)

Dichlorido[N,N'-(cyclohexane-1,2-diylidene)bis(4-fluorobenzohydrazide)-κ²N',O]zinc(II) (shelx_1)

Crystal data

[ZnCl2(C20H18F2N4O2)]	F(000) = 1056
Mr = 520.65	Dx = 1.587 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.7682 (5) Å	Cell parameters from 19667 reflections
b = 17.3071 (7) Å	θ = 2.0–30.6°
c = 13.3524 (7) Å	µ = 1.41 mm^−1
β = 105.165 (4)°	T = 296 K
V = 2178.74 (19) Å^3	Prism, yellow
Z = 4	0.64 × 0.38 × 0.22 mm

Data collection

Stoe IPDS 2 diffractometer	6409 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3712 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.078
Detector resolution: 6.67 pixels mm^-1	θmax = 30.2°, θmin = 2.0°
rotation method scans	h = −13→13
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −24→23
Tmin = 0.510, Tmax = 0.767	l = −18→18
21812 measured reflections

Refinement

Refinement on F^2	48 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.077	H-atom parameters constrained
wR(F^2) = 0.199	w = 1/[σ^2(Fo^2) + (0.0859P)^2 + 1.9025P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
6409 reflections	Δρmax = 0.52 e Å^−3
281 parameters	Δρmin = −0.47 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

STOE diffractometer equipped with an IPDS II image plate detector was used to collect the crystal data of L^F, 1 and 2. The collection was carried out at room temperature (296K) using graphite monochromated Mo Kα radiation (λ=0.71073Å) inω-scanning mode. SHELXS-97(Sheldrick, 1997)was used to solve (direct methods) and refine (full-matrix least-squares method) the structures, implemented in the WinGX (Farrugia, 1999)program suite.

Data collection: X-AREA and data reduction: X-RED32 (Cie, 2002). All non-hydrogen atoms were assigned anisotropic thermal parameters. Experimental details of the crystal data, data collection and refinement are illustrated inTable 1. The structure analysis and presentation of the results were done by the general-purpose crystallographic tool PLATON(Spek, 2009), while themolecular graphics were made by ORTEP-3 for Windows(Farrugia, 1997).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.19181 (6)	0.70598 (3)	0.54901 (5)	0.05246 (18)
Cl2	0.01999 (14)	0.77893 (8)	0.46033 (13)	0.0703 (4)
Cl1	0.2705 (2)	0.71079 (10)	0.71779 (12)	0.0819 (4)
O1	0.1684 (3)	0.59503 (19)	0.4980 (3)	0.0571 (8)
F2	0.2590 (4)	0.27168 (18)	0.3162 (3)	0.0835 (11)
N3	0.5860 (4)	0.6720 (2)	0.3910 (3)	0.0492 (8)
N1	0.3594 (4)	0.6238 (2)	0.4391 (3)	0.0483 (8)
H1	0.421951	0.610293	0.407526	0.058*
N4	0.6968 (4)	0.6576 (2)	0.3497 (3)	0.0508 (9)
H4	0.758323	0.692937	0.348394	0.061*
N2	0.3557 (4)	0.6969 (2)	0.4781 (3)	0.0473 (8)
F1	1.1319 (5)	0.5202 (3)	0.1138 (3)	0.1075 (14)
O2	0.6224 (5)	0.5357 (3)	0.3142 (4)	0.0893 (15)
C1	0.2586 (5)	0.5739 (3)	0.4532 (4)	0.0483 (9)
C8	0.4467 (5)	0.7493 (2)	0.4697 (4)	0.0466 (9)
C2	0.2610 (5)	0.4946 (3)	0.4151 (4)	0.0479 (9)
C16	0.9308 (5)	0.6247 (3)	0.2591 (4)	0.0529 (11)
H16	0.930078	0.672740	0.290291	0.064*
C15	0.8279 (5)	0.5709 (3)	0.2626 (3)	0.0482 (10)
C14	0.7081 (5)	0.5858 (3)	0.3104 (4)	0.0538 (11)
C3	0.3707 (5)	0.4666 (3)	0.3757 (4)	0.0549 (11)
H3	0.444737	0.499317	0.371927	0.066*
C17	1.0353 (5)	0.6076 (3)	0.2094 (4)	0.0620 (13)
H17	1.105896	0.643234	0.207633	0.074*
C13	0.5671 (5)	0.7398 (3)	0.4236 (4)	0.0473 (9)
C4	0.3709 (6)	0.3914 (3)	0.3426 (4)	0.0582 (12)
H4A	0.444624	0.372141	0.317747	0.070*
C7	0.1485 (5)	0.4456 (3)	0.4166 (4)	0.0591 (12)
H7	0.073834	0.463939	0.441126	0.071*
C18	1.0318 (6)	0.5371 (4)	0.1633 (5)	0.0693 (15)
C5	0.2581 (6)	0.3460 (3)	0.3475 (4)	0.0580 (12)
C20	0.8284 (6)	0.5001 (3)	0.2158 (5)	0.0647 (13)
H20	0.758710	0.464022	0.218068	0.078*
C12	0.6609 (7)	0.8080 (3)	0.4220 (6)	0.0733 (13)
H12A	0.752590	0.797740	0.469714	0.088*
H12B	0.675424	0.811855	0.353031	0.088*
C6	0.1464 (7)	0.3714 (3)	0.3828 (5)	0.0679 (14)
H6	0.071023	0.338822	0.383577	0.082*
C19	0.9318 (7)	0.4819 (4)	0.1652 (5)	0.0773 (17)
H19	0.933085	0.434035	0.133773	0.093*
C9	0.4196 (7)	0.8266 (3)	0.5119 (6)	0.0737 (13)
H9A	0.334071	0.847954	0.466134	0.088*
H9B	0.400906	0.818418	0.578941	0.088*
C10	0.5312 (8)	0.8836 (4)	0.5243 (6)	0.0833 (12)
H10A	0.488976	0.934266	0.524712	0.100*
H10B	0.596824	0.875944	0.591942	0.100*
C11	0.6105 (8)	0.8841 (4)	0.4491 (6)	0.0845 (12)
H11A	0.692419	0.917203	0.474247	0.101*
H11B	0.552395	0.907309	0.386107	0.101*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0449 (3)	0.0530 (3)	0.0640 (3)	0.0010 (2)	0.0223 (2)	−0.0069 (3)
Cl2	0.0520 (7)	0.0632 (7)	0.0941 (10)	0.0091 (6)	0.0165 (7)	−0.0010 (7)
Cl1	0.0963 (11)	0.0831 (10)	0.0636 (8)	0.0024 (9)	0.0163 (8)	−0.0063 (7)
O1	0.0519 (18)	0.0521 (18)	0.074 (2)	−0.0067 (15)	0.0275 (17)	−0.0095 (16)
F2	0.113 (3)	0.0467 (15)	0.103 (3)	−0.0188 (17)	0.048 (2)	−0.0197 (16)
N3	0.0446 (19)	0.051 (2)	0.056 (2)	0.0066 (16)	0.0215 (17)	−0.0021 (17)
N1	0.0435 (18)	0.0417 (18)	0.063 (2)	0.0012 (15)	0.0187 (17)	−0.0063 (16)
N4	0.052 (2)	0.0467 (19)	0.062 (2)	0.0044 (16)	0.0289 (19)	0.0025 (17)
N2	0.0429 (17)	0.0418 (18)	0.062 (2)	0.0013 (14)	0.0216 (16)	−0.0084 (16)
F1	0.099 (3)	0.135 (4)	0.113 (3)	0.027 (3)	0.070 (3)	−0.011 (3)
O2	0.078 (3)	0.076 (3)	0.136 (4)	−0.028 (2)	0.067 (3)	−0.037 (3)
C1	0.045 (2)	0.046 (2)	0.053 (2)	−0.0015 (18)	0.012 (2)	−0.0036 (19)
C8	0.044 (2)	0.042 (2)	0.055 (2)	0.0002 (17)	0.0153 (19)	−0.0070 (18)
C2	0.049 (2)	0.044 (2)	0.052 (2)	0.0013 (18)	0.014 (2)	0.0011 (18)
C16	0.053 (2)	0.051 (2)	0.058 (3)	0.009 (2)	0.020 (2)	0.004 (2)
C15	0.048 (2)	0.052 (2)	0.047 (2)	0.0099 (19)	0.016 (2)	0.0032 (19)
C14	0.050 (2)	0.058 (3)	0.059 (3)	0.005 (2)	0.023 (2)	−0.002 (2)
C3	0.055 (3)	0.045 (2)	0.069 (3)	−0.008 (2)	0.024 (2)	−0.009 (2)
C17	0.051 (3)	0.074 (3)	0.068 (3)	0.004 (2)	0.028 (2)	0.010 (3)
C13	0.044 (2)	0.048 (2)	0.052 (2)	0.0010 (18)	0.0169 (19)	−0.0048 (19)
C4	0.065 (3)	0.048 (2)	0.065 (3)	−0.002 (2)	0.023 (3)	−0.009 (2)
C7	0.054 (3)	0.056 (3)	0.072 (3)	−0.007 (2)	0.025 (2)	−0.003 (2)
C18	0.071 (3)	0.081 (4)	0.067 (3)	0.020 (3)	0.037 (3)	0.003 (3)
C5	0.079 (3)	0.041 (2)	0.056 (3)	−0.007 (2)	0.022 (3)	−0.0051 (19)
C20	0.060 (3)	0.061 (3)	0.076 (4)	0.002 (2)	0.023 (3)	−0.012 (3)
C12	0.073 (3)	0.060 (2)	0.101 (3)	−0.009 (2)	0.047 (3)	−0.003 (2)
C6	0.073 (3)	0.059 (3)	0.079 (4)	−0.023 (3)	0.031 (3)	−0.006 (3)
C19	0.090 (4)	0.070 (4)	0.077 (4)	0.021 (3)	0.030 (3)	−0.020 (3)
C9	0.078 (3)	0.053 (2)	0.107 (3)	−0.0073 (19)	0.053 (3)	−0.019 (2)
C10	0.087 (3)	0.059 (2)	0.117 (3)	−0.0146 (19)	0.049 (2)	−0.018 (2)
C11	0.088 (3)	0.061 (2)	0.117 (3)	−0.014 (2)	0.049 (2)	−0.014 (2)

Geometric parameters (Å, º)

Zn1—O1	2.030 (3)	C3—C4	1.375 (7)
Zn1—N2	2.068 (3)	C3—H3	0.9300
Zn1—Cl1	2.1842 (17)	C17—C18	1.363 (8)
Zn1—Cl2	2.1848 (15)	C17—H17	0.9300
O1—C1	1.243 (5)	C13—C12	1.497 (7)
F2—C5	1.353 (6)	C4—C5	1.368 (7)
N3—C13	1.281 (6)	C4—H4A	0.9300
N3—N4	1.360 (5)	C7—C6	1.360 (8)
N1—C1	1.360 (6)	C7—H7	0.9300
N1—N2	1.372 (5)	C18—C19	1.372 (9)
N1—H1	0.8600	C5—C6	1.370 (8)
N4—C14	1.366 (6)	C20—C19	1.391 (8)
N4—H4	0.8600	C20—H20	0.9300
N2—C8	1.296 (5)	C12—C11	1.484 (8)
F1—C18	1.347 (6)	C12—H12A	0.9700
O2—C14	1.215 (6)	C12—H12B	0.9700
C1—C2	1.466 (6)	C6—H6	0.9300
C8—C13	1.472 (6)	C19—H19	0.9300
C8—C9	1.502 (6)	C9—C10	1.447 (8)
C2—C7	1.392 (6)	C9—H9A	0.9700
C2—C3	1.398 (6)	C9—H9B	0.9700
C16—C15	1.380 (7)	C10—C11	1.420 (9)
C16—C17	1.388 (7)	C10—H10A	0.9700
C16—H16	0.9300	C10—H10B	0.9700
C15—C20	1.377 (7)	C11—H11A	0.9700
C15—C14	1.494 (6)	C11—H11B	0.9700
O1—Zn1—N2	78.88 (13)	C5—C4—H4A	121.3
O1—Zn1—Cl1	111.12 (12)	C3—C4—H4A	121.3
N2—Zn1—Cl1	111.68 (13)	C6—C7—C2	120.9 (5)
O1—Zn1—Cl2	111.20 (12)	C6—C7—H7	119.5
N2—Zn1—Cl2	111.90 (12)	C2—C7—H7	119.5
Cl1—Zn1—Cl2	123.39 (7)	F1—C18—C17	118.7 (6)
C1—O1—Zn1	114.1 (3)	F1—C18—C19	118.0 (5)
C13—N3—N4	120.4 (4)	C17—C18—C19	123.3 (5)
C1—N1—N2	116.1 (3)	F2—C5—C4	117.4 (5)
C1—N1—H1	121.9	F2—C5—C6	118.8 (5)
N2—N1—H1	121.9	C4—C5—C6	123.8 (5)
N3—N4—C14	118.4 (4)	C15—C20—C19	120.8 (5)
N3—N4—H4	120.8	C15—C20—H20	119.6
C14—N4—H4	120.8	C19—C20—H20	119.6
C8—N2—N1	121.7 (3)	C11—C12—C13	116.9 (5)
C8—N2—Zn1	128.1 (3)	C11—C12—H12A	108.1
N1—N2—Zn1	110.2 (3)	C13—C12—H12A	108.1
O1—C1—N1	120.7 (4)	C11—C12—H12B	108.1
O1—C1—C2	121.4 (4)	C13—C12—H12B	108.1
N1—C1—C2	117.9 (4)	H12A—C12—H12B	107.3
N2—C8—C13	126.9 (4)	C7—C6—C5	118.2 (5)
N2—C8—C9	113.5 (4)	C7—C6—H6	120.9
C13—C8—C9	119.7 (4)	C5—C6—H6	120.9
C7—C2—C3	118.7 (4)	C18—C19—C20	117.6 (5)
C7—C2—C1	118.7 (4)	C18—C19—H19	121.2
C3—C2—C1	122.6 (4)	C20—C19—H19	121.2
C15—C16—C17	120.4 (5)	C10—C9—C8	116.7 (5)
C15—C16—H16	119.8	C10—C9—H9A	108.1
C17—C16—H16	119.8	C8—C9—H9A	108.1
C20—C15—C16	119.8 (4)	C10—C9—H9B	108.1
C20—C15—C14	116.3 (4)	C8—C9—H9B	108.1
C16—C15—C14	123.9 (4)	H9A—C9—H9B	107.3
O2—C14—N4	120.5 (4)	C11—C10—C9	117.2 (6)
O2—C14—C15	121.4 (4)	C11—C10—H10A	108.0
N4—C14—C15	118.1 (4)	C9—C10—H10A	108.0
C4—C3—C2	121.0 (4)	C11—C10—H10B	108.0
C4—C3—H3	119.5	C9—C10—H10B	108.0
C2—C3—H3	119.5	H10A—C10—H10B	107.2
C18—C17—C16	118.2 (5)	C10—C11—C12	116.4 (6)
C18—C17—H17	120.9	C10—C11—H11A	108.2
C16—C17—H17	120.9	C12—C11—H11A	108.2
N3—C13—C8	116.5 (4)	C10—C11—H11B	108.2
N3—C13—C12	125.0 (4)	C12—C11—H11B	108.2
C8—C13—C12	118.5 (4)	H11A—C11—H11B	107.4
C5—C4—C3	117.3 (5)
C13—N3—N4—C14	−176.2 (5)	N4—N3—C13—C12	−0.9 (8)
C1—N1—N2—C8	179.7 (4)	N2—C8—C13—N3	−2.0 (8)
C1—N1—N2—Zn1	0.5 (5)	C9—C8—C13—N3	178.6 (5)
Zn1—O1—C1—N1	−1.7 (6)	N2—C8—C13—C12	−179.6 (5)
Zn1—O1—C1—C2	177.6 (3)	C9—C8—C13—C12	1.0 (8)
N2—N1—C1—O1	0.8 (7)	C2—C3—C4—C5	1.4 (8)
N2—N1—C1—C2	−178.5 (4)	C3—C2—C7—C6	1.5 (8)
N1—N2—C8—C13	−2.7 (7)	C1—C2—C7—C6	−179.5 (5)
Zn1—N2—C8—C13	176.5 (4)	C16—C17—C18—F1	179.3 (5)
N1—N2—C8—C9	176.7 (5)	C16—C17—C18—C19	−1.2 (9)
Zn1—N2—C8—C9	−4.2 (7)	C3—C4—C5—F2	−179.1 (5)
O1—C1—C2—C7	8.9 (7)	C3—C4—C5—C6	0.4 (9)
N1—C1—C2—C7	−171.8 (5)	C16—C15—C20—C19	0.2 (8)
O1—C1—C2—C3	−172.1 (5)	C14—C15—C20—C19	177.2 (5)
N1—C1—C2—C3	7.2 (7)	N3—C13—C12—C11	171.5 (6)
C17—C16—C15—C20	−0.5 (8)	C8—C13—C12—C11	−11.1 (9)
C17—C16—C15—C14	−177.3 (5)	C2—C7—C6—C5	0.3 (9)
N3—N4—C14—O2	−1.4 (8)	F2—C5—C6—C7	178.3 (5)
N3—N4—C14—C15	178.4 (4)	C4—C5—C6—C7	−1.2 (9)
C20—C15—C14—O2	5.3 (8)	F1—C18—C19—C20	−179.6 (6)
C16—C15—C14—O2	−177.8 (5)	C17—C18—C19—C20	1.0 (10)
C20—C15—C14—N4	−174.4 (5)	C15—C20—C19—C18	−0.4 (9)
C16—C15—C14—N4	2.4 (7)	N2—C8—C9—C10	168.1 (6)
C7—C2—C3—C4	−2.3 (8)	C13—C8—C9—C10	−12.5 (9)
C1—C2—C3—C4	178.7 (5)	C8—C9—C10—C11	35.5 (10)
C15—C16—C17—C18	1.0 (8)	C9—C10—C11—C12	−46.5 (11)
N4—N3—C13—C8	−178.3 (4)	C13—C12—C11—C10	33.6 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3	0.86	1.99	2.5986 (4)	127

Dichlorido[N,N'-(cyclohexane-1,2-diylidene)bis(4-fluorobenzohydrazide)-κ⁴O,N,N',O']mercury(II) (shelx_2)

Crystal data

[HgCl2(C20H18F2N4O2)]	F(000) = 1256
Mr = 655.87	Dx = 2.008 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.4902 (4) Å	Cell parameters from 14848 reflections
b = 16.7227 (8) Å	θ = 2.3–31.5°
c = 12.6827 (5) Å	µ = 7.38 mm^−1
β = 102.769 (3)°	T = 296 K
V = 2169.83 (16) Å^3	Prism, yellow
Z = 4	0.47 × 0.27 × 0.12 mm

Data collection

Stoe IPDS 2 diffractometer	1875 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1756 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.047
Detector resolution: 6.67 pixels mm^-1	θmax = 25.1°, θmin = 2.3°
rotation method scans	h = −12→12
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −19→19
Tmin = 0.207, Tmax = 0.498	l = −13→14
7006 measured reflections

Refinement

Refinement on F^2	71 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.025	H-atom parameters constrained
wR(F^2) = 0.062	w = 1/[σ^2(Fo^2) + (0.0337P)^2 + 2.9357P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.002
1875 reflections	Δρmax = 0.94 e Å^−3
141 parameters	Δρmin = −0.72 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. STOE diffractometer equipped with an IPDS II image plate detector was used to collect the crystal data of L^F, 1 and 2. The collection was carried out at room temperature (296K) using graphite monochromated Mo Kα radiation (λ=0.71073Å) inω-scanning mode. SHELXS-97(Sheldrick, 1997)was used to solve (direct methods) and refine (full-matrix least-squares method) the structures, implemented in the WinGX (Farrugia, 1999)program suite.

Data collection: X-AREA and data reduction: X-RED32 (Cie, 2002). All non-hydrogen atoms were assigned anisotropic thermal parameters. Experimental details of the crystal data, data collection and refinement are illustrated inTable 1. The structure analysis and presentation of the results were done by the general-purpose crystallographic tool PLATON(Spek, 2009), while themolecular graphics were made by ORTEP-3 for Windows(Farrugia, 1997).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Hg1	0.500000	0.65290 (2)	0.750000	0.04720 (11)
F1	1.0855 (3)	0.5866 (2)	0.3494 (3)	0.0696 (8)
N2	0.6516 (3)	0.51689 (19)	0.6058 (3)	0.0424 (7)
H2	0.690358	0.474158	0.591702	0.051*
C3	0.8594 (5)	0.6532 (2)	0.5040 (4)	0.0511 (11)
H3	0.843729	0.697804	0.542989	0.061*
C8	0.5457 (4)	0.4456 (2)	0.7125 (3)	0.0382 (7)
C4	0.9615 (5)	0.6542 (3)	0.4522 (5)	0.0547 (11)
H4	1.015527	0.698667	0.455775	0.066*
C2	0.7790 (4)	0.5863 (2)	0.4991 (4)	0.0402 (9)
C9	0.6077 (5)	0.3686 (2)	0.6904 (4)	0.0513 (9)
H9A	0.585428	0.358532	0.613139	0.062*
H9B	0.701942	0.374285	0.711759	0.062*
C5	0.9806 (4)	0.5882 (3)	0.3957 (4)	0.0489 (10)
C1	0.6763 (4)	0.5882 (2)	0.5626 (4)	0.0459 (10)
C7	0.7989 (4)	0.5215 (2)	0.4369 (4)	0.0422 (9)
H7	0.743705	0.477409	0.430856	0.051*
C10	0.5677 (6)	0.2982 (3)	0.7473 (6)	0.0685 (12)
H10A	0.585476	0.249945	0.710576	0.082*
H10B	0.620898	0.296542	0.820238	0.082*
C6	0.9004 (5)	0.5220 (3)	0.3838 (4)	0.0488 (10)
H6	0.914304	0.478947	0.341211	0.059*
N1	0.5645 (3)	0.5138 (2)	0.6718 (3)	0.0405 (6)
O2	0.6206 (5)	0.64934 (19)	0.5777 (4)	0.0746 (13)
Cl1	0.69446 (14)	0.68047 (9)	0.87181 (15)	0.0789 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Hg1	0.04234 (14)	0.04600 (15)	0.05688 (18)	0.000	0.01874 (10)	0.000
F1	0.0507 (15)	0.106 (2)	0.062 (2)	0.0051 (15)	0.0333 (14)	0.0133 (16)
N2	0.0440 (16)	0.0395 (15)	0.052 (2)	0.0048 (13)	0.0288 (13)	0.0030 (13)
C3	0.059 (3)	0.042 (2)	0.059 (3)	−0.0009 (19)	0.027 (2)	−0.0013 (19)
C8	0.0359 (15)	0.0380 (13)	0.0455 (19)	−0.0002 (13)	0.0194 (15)	−0.0001 (12)
C4	0.051 (3)	0.054 (2)	0.064 (3)	−0.013 (2)	0.021 (2)	0.006 (2)
C2	0.044 (2)	0.0378 (19)	0.043 (2)	0.0029 (16)	0.0184 (18)	0.0071 (16)
C9	0.0517 (19)	0.0437 (16)	0.066 (2)	0.0059 (15)	0.0296 (17)	−0.0036 (16)
C5	0.036 (2)	0.072 (3)	0.042 (3)	0.0020 (19)	0.0165 (18)	0.012 (2)
C1	0.050 (2)	0.041 (2)	0.053 (3)	0.0035 (18)	0.026 (2)	0.0062 (18)
C7	0.046 (2)	0.041 (2)	0.041 (2)	−0.0002 (17)	0.0138 (18)	0.0022 (16)
C10	0.075 (3)	0.049 (2)	0.092 (3)	0.004 (2)	0.043 (2)	0.005 (2)
C6	0.054 (2)	0.058 (3)	0.037 (3)	0.010 (2)	0.0181 (19)	0.0000 (18)
N1	0.0379 (14)	0.0427 (10)	0.0470 (18)	0.0012 (12)	0.0228 (12)	0.0050 (10)
O2	0.097 (3)	0.0472 (18)	0.103 (3)	0.0241 (18)	0.073 (3)	0.0219 (17)
Cl1	0.0568 (7)	0.0628 (7)	0.1067 (12)	−0.0105 (6)	−0.0044 (7)	0.0040 (7)

Geometric parameters (Å, º)

Hg1—Cl1	2.3167 (14)	C4—C5	1.354 (7)
Hg1—Cl1^i	2.3168 (14)	C4—H4	0.9300
Hg1—N1	2.674 (3)	C2—C7	1.383 (6)
Hg1—N1^i	2.674 (3)	C2—C1	1.481 (6)
Hg1—O1	2.757	C9—C10	1.489 (6)
Hg1—O2	2.757	C9—H9A	0.9700
F1—C5	1.358 (5)	C9—H9B	0.9700
N2—C1	1.361 (5)	C5—C6	1.379 (7)
N2—N1	1.371 (4)	C1—O2	1.213 (5)
N2—H2	0.8600	C7—C6	1.380 (6)
C3—C4	1.375 (7)	C7—H7	0.9300
C3—C2	1.394 (6)	C10—C10^i	1.437 (11)
C3—H3	0.9300	C10—H10A	0.9700
C8—N1	1.284 (5)	C10—H10B	0.9700
C8—C8^i	1.493 (7)	C6—H6	0.9300
C8—C9	1.497 (6)
Cl1—Hg1—Cl1^i	157.05 (8)	C8—C9—H9A	108.7
Cl1—Hg1—N1	99.37 (9)	C10—C9—H9B	108.7
Cl1^i—Hg1—N1	100.57 (9)	C8—C9—H9B	108.7
Cl1—Hg1—N1^i	100.57 (9)	H9A—C9—H9B	107.6
Cl1^i—Hg1—N1^i	99.37 (9)	C4—C5—F1	118.3 (4)
Cl1—Hg1—O2	92.42 (9)	C4—C5—C6	123.7 (4)
Cl1—Hg1—O2^i	88.08 (9)	F1—C5—C6	118.0 (4)
N1—Hg1—N1^i	59.05 (14)	O2—C1—N2	122.3 (4)
C1—N2—N1	119.4 (3)	O2—C1—C2	122.5 (4)
C1—N2—H2	120.3	N2—C1—C2	115.2 (3)
N1—N2—H2	120.3	C6—C7—C2	120.3 (4)
C4—C3—C2	121.1 (4)	C6—C7—H7	119.9
C4—C3—H3	119.4	C2—C7—H7	119.9
C2—C3—H3	119.4	C10^i—C10—C9	114.3 (5)
N1—C8—C8^i	115.7 (2)	C10^i—C10—H10A	108.7
N1—C8—C9	125.2 (3)	C9—C10—H10A	108.7
C8^i—C8—C9	119.1 (2)	C10^i—C10—H10B	108.7
C5—C4—C3	117.7 (4)	C9—C10—H10B	108.7
C5—C4—H4	121.2	H10A—C10—H10B	107.6
C3—C4—H4	121.2	C5—C6—C7	118.0 (4)
C7—C2—C3	119.2 (4)	C5—C6—H6	121.0
C7—C2—C1	123.2 (4)	C7—C6—H6	121.0
C3—C2—C1	117.6 (4)	C8—N1—N2	117.5 (3)
C10—C9—C8	114.1 (4)	C8—N1—Hg1	123.3 (3)
C10—C9—H9A	108.7	N2—N1—Hg1	116.8 (2)
C2—C3—C4—C5	0.4 (8)	C3—C2—C7—C6	2.5 (7)
C4—C3—C2—C7	−3.0 (7)	C1—C2—C7—C6	−176.9 (4)
C4—C3—C2—C1	176.4 (5)	C8—C9—C10—C10^i	38.4 (9)
N1—C8—C9—C10	−179.3 (5)	C4—C5—C6—C7	−3.3 (7)
C8^i—C8—C9—C10	0.7 (8)	F1—C5—C6—C7	175.7 (4)
C3—C4—C5—F1	−176.2 (4)	C2—C7—C6—C5	0.6 (7)
C3—C4—C5—C6	2.8 (8)	C8^i—C8—N1—N2	177.6 (4)
N1—N2—C1—O2	−2.4 (7)	C9—C8—N1—N2	−2.4 (7)
N1—N2—C1—C2	175.7 (4)	C8^i—C8—N1—Hg1	15.7 (6)
C7—C2—C1—O2	−147.4 (5)	C9—C8—N1—Hg1	−164.3 (4)
C3—C2—C1—O2	33.3 (7)	C1—N2—N1—C8	−178.7 (4)
C7—C2—C1—N2	34.6 (6)	C1—N2—N1—Hg1	−15.6 (5)
C3—C2—C1—N2	−144.8 (4)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···F1^ii	0.86	2.52	3.198 (4)	137
C9—H9B···F1^ii	0.97	2.60	3.447 (5)	146

Symmetry code: (ii) −x+2, −y+1, −z+1.