(Aceto­nitrile-κN)chlorido­{2-[4-(3,5-di­fluorophen­yl)-6-phenyl­pyridin-2-yl]phen­yl-κ2C1,N}platinum(II)

Wang, Y.; Li, H.; Shen, Y.; Wu, J.

doi:10.1107/S2414314619002943

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 3| March 2019| x190294

https://doi.org/10.1107/S2414314619002943

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(Acetonitrile-κN)chlorido{2-[4-(3,5-difluorophenyl)-6-phenylpyridin-2-yl]phenyl-κ²C¹,N}platinum(II)

Yiwen Wang,^a Hu Li,^a Yu Shen ^a and Jieying Wu ^a ^*

^aDepartment of Chemistry, Anhui University, Hefei 230601, Peoples Republic of China, Key Laboratory of Functional Inorganic Materials, Chemistry, Hefei 230601, People's Republic of China
^*Correspondence e-mail: jywu1957@163.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 28 January 2019; accepted 26 February 2019; online 7 March 2019)

The title compound, [Pt(C₂₃H₁₄F₂N)Cl(CH₃CN)], comprises of a Pt^II atom in a distorted square-planar coordination, defined by a C,N-chelating 4-(3,5-difluorophenyl)-2,6-diphenylpyridine ligand, a chlorido and an acetonitrile ligand. Hydrogen-bonding interactions between the H atoms of the 3,5-difluorophenyl ring and the acetonitrile ligand with Cl and F acceptor atoms of neighbouring ligands consolidate the packing.

Keywords: crystal structure; platinum(II) complex; (C,N)-chelating ligand.

CCDC reference: 1899620

Structure description

Platinum complexes have received attention because of their chemical and photophysical properties, such as high stabilities, emissions in the visible region, high fluorescent quantum yields and long excited lifetimes (Fang et al., 2018 ). In this study, we report the crystal structure of a novel platinum(II) complex, [PtCl(C₂₃H₁₄F₂N)(CH₃CN)].

The platinum(II) atom has a distorted square-planar coordination environment defined by a (C,N)-chelating 4-(3,5-difluorophenyl)-2,6-diphenylpyridine ligand, one chlorido ligand and one acetonitrile ligand (Fig. 1). Relevant bond lengths and angles are given in Table 1. The considerable distortion from planarity is reflected by the r.m.s. deviation of 0.1265 Å of the least-squares plane through Pt1, C1, N1, C2, with a highest deviation of 0.1641 (12) Å for C1. The chelating ligand is not planar, with dihedral angles between the central pyridine ring and the two phenyl rings of 3.88 (13)° for ring C1–C6 and of 52.97 (14)° for ring C18–C23; the dihedral angle between the central pyridine ring and the difluorophenyl ring amounts to 20.35 (13)°. The bond length between C9 and C10 of 1.487 (4) Å is intermediate between a single and double C—C bond and thus indicates a highly π-conjugated system (Coe, 2013 ). As shown in Fig. 2, there are intermolecular hydrogen bonds between one H atom of the 3,5-difluorophenyl ring and the Cl atom, and between the acetonitrile ligand and F and Cl atoms of neighbouring molecules (Table 2), leading to the formation of a three-dimensional network.

Table 1
Selected geometric parameters (Å, °)

Pt1—C1	1.981 (3)	Pt1—N2	2.106 (2)
Pt1—N1	2.046 (2)	Pt1—Cl1	2.3036 (9)

C1—Pt1—N1	81.55 (10)	C1—Pt1—Cl1	93.84 (8)
C1—Pt1—N2	166.63 (10)	N1—Pt1—Cl1	174.90 (6)
N1—Pt1—N2	99.24 (9)	N2—Pt1—Cl1	85.75 (7)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Cl1ⁱ	0.93	2.77	3.545 (3)	142
C25—H25A⋯F1ⁱⁱ	0.96	2.42	3.202 (4)	138
C25—H25B⋯Cl1ⁱⁱⁱ	0.96	2.66	3.613 (3)	169
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y+2, -z+1.

Figure 1
The molecular structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level; H atoms were omitted for clarity.

Figure 2
Hydrogen bonding in the title compound, shown as dashed lines.

Synthesis and crystallization

4-(3,5-Difluorophenyl)-2,6-diphenylpyridine 0.35 g (1 mmol), potassium hexachloridoplatinate 0.41 g (1 mmol) and 100 ml glacial acetic acid were added to a 250 ml round-bottom flask at room temperature and stirred for 10 min. After dissolution, the temperature was raised to 403 K for 72 h during which time the reaction mixture was slowly converted from a colourless liquid to a yellow solid. The solid was filtered when cooling to room temperature and washed by acetone. Yellow crystals for X-ray analysis were obtained from an acetonitrile solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3.

Table 3
Experimental details

Crystal data
Chemical formula	[Pt(C₂₃H₁₄F₂N)Cl(C₂H₃N)]
M_r	613.94
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.770 (5), 18.226 (5), 13.670 (5)
β (°)	104.414 (5)
V (Å³)	2116.3 (15)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	6.79
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.235, 0.344
No. of measured, independent and observed [I > 2σ(I)] reflections	15021, 3835, 3578
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.016, 0.040, 1.07
No. of reflections	3835
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.60
Computer programs: APEX2 and SAINT (Bruker, 2004), SHELXT2014 (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), DIAMOND (Brandenburg, 2016 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1899620

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619002943/wm4099sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619002943/wm4099Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2016); software used to prepare material for publication: publCIF (Westrip, 2010).

(Acetonitrile-κN)chlorido{2-[4-(3,5-difluorophenyl)-6-phenylpyridin-2-yl]phenylκ²C¹,N}platinum(II) top

Crystal data top

[Pt(C₂₃H₁₄F₂N)Cl(C₂H₃N)]	F(000) = 1176
M_r = 613.94	D_x = 1.927 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
a = 8.770 (5) Å	Cell parameters from 9960 reflections
b = 18.226 (5) Å	θ = 2.2–27.2°
c = 13.670 (5) Å	µ = 6.79 mm⁻¹
β = 104.414 (5)°	T = 298 K
V = 2116.3 (15) Å³	Block, yellow
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker APEXII CCD diffractometer	3578 reflections with I > 2σ(I)
ω scans	R_int = 0.023
Absorption correction: multi-scan (SADABS; Bruker, 2004)	θ_max = 25.3°, θ_min = 1.9°
T_min = 0.235, T_max = 0.344	h = −10→10
15021 measured reflections	k = −21→18
3835 independent reflections	l = −16→16

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.016	H-atom parameters constrained
wR(F²) = 0.040	w = 1/[σ²(F_o²) + (0.016P)² + 2.1931P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.009
3835 reflections	Δρ_max = 0.63 e Å⁻³
281 parameters	Δρ_min = −0.60 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Pt1	0.55963 (2)	1.05151 (2)	0.78384 (2)	0.02038 (5)
Cl1	0.38721 (9)	1.13087 (4)	0.68065 (5)	0.03611 (18)
C14	1.1855 (3)	0.76355 (16)	1.1856 (2)	0.0275 (6)
C5	0.6207 (3)	1.09210 (15)	1.0927 (2)	0.0231 (6)
H5	0.670223	1.066195	1.150455	0.028*
C23	0.8746 (3)	0.98091 (17)	0.7086 (2)	0.0260 (6)
H23	0.887401	1.027274	0.737952	0.031*
C2	0.4788 (3)	1.17075 (15)	0.9194 (2)	0.0250 (6)
H2	0.432728	1.198285	0.862429	0.030*
C9	0.8932 (3)	0.89937 (15)	1.04021 (19)	0.0212 (5)
F1	1.3038 (2)	0.72059 (11)	1.16971 (13)	0.0432 (5)
C21	0.8798 (4)	0.90177 (19)	0.5687 (2)	0.0361 (7)
H21	0.896266	0.894923	0.504660	0.043*
C4	0.5330 (3)	1.15460 (15)	1.1003 (2)	0.0250 (6)
H4	0.519379	1.169482	1.162604	0.030*
C15	1.1063 (3)	0.80721 (15)	1.1077 (2)	0.0248 (6)
H15	1.134651	0.808001	1.046567	0.030*
C3	0.4662 (3)	1.19436 (15)	1.0137 (2)	0.0259 (6)
H3	0.412038	1.237496	1.018825	0.031*
C24	0.4648 (4)	0.94075 (16)	0.5940 (2)	0.0259 (6)
C1	0.5593 (3)	1.10670 (14)	0.90866 (19)	0.0205 (5)
C22	0.9030 (4)	0.97014 (19)	0.6141 (2)	0.0347 (7)
H22	0.937678	1.009018	0.581218	0.042*
N1	0.7183 (3)	0.98863 (12)	0.88429 (16)	0.0199 (5)
C7	0.7222 (3)	1.00335 (14)	0.98306 (19)	0.0192 (5)
C18	0.8269 (3)	0.92247 (15)	0.75956 (19)	0.0211 (6)
C16	0.8928 (3)	0.88772 (15)	0.93942 (19)	0.0220 (6)
H16	0.949692	0.848666	0.922713	0.026*
N2	0.5145 (3)	0.98045 (14)	0.65843 (17)	0.0260 (5)
C25	0.4001 (4)	0.88949 (18)	0.5126 (2)	0.0363 (7)
H25A	0.400044	0.840932	0.539824	0.054*
H25B	0.463395	0.890171	0.464547	0.054*
H25C	0.294251	0.903555	0.479812	0.054*
C17	0.8092 (3)	0.93322 (14)	0.8635 (2)	0.0202 (6)
C10	0.9817 (3)	0.85061 (14)	1.12207 (19)	0.0197 (5)
C6	0.6342 (3)	1.06843 (14)	0.9978 (2)	0.0204 (6)
C20	0.8323 (4)	0.84396 (18)	0.6188 (2)	0.0327 (7)
H20	0.816887	0.798020	0.588359	0.039*
C19	0.8072 (3)	0.85342 (16)	0.7143 (2)	0.0266 (6)
H19	0.777268	0.813748	0.748059	0.032*
C11	0.9428 (3)	0.84817 (16)	1.21572 (18)	0.0234 (6)
H11	0.859429	0.875703	1.226834	0.028*
C8	0.8095 (3)	0.95953 (14)	1.06091 (19)	0.0201 (6)
H8	0.811555	0.970849	1.127560	0.024*
C12	1.0303 (3)	0.80438 (16)	1.29028 (19)	0.0248 (6)
C13	1.1537 (3)	0.76078 (17)	1.2789 (2)	0.0282 (6)
H13	1.211236	0.731568	1.330846	0.034*
F2	0.9943 (2)	0.80220 (10)	1.38172 (12)	0.0373 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.02230 (7)	0.02281 (7)	0.01527 (6)	0.00164 (4)	0.00324 (4)	0.00162 (4)
Cl1	0.0398 (4)	0.0472 (5)	0.0205 (3)	0.0205 (4)	0.0060 (3)	0.0072 (3)
C14	0.0213 (14)	0.0318 (16)	0.0297 (15)	0.0065 (12)	0.0070 (12)	0.0021 (12)
C5	0.0257 (15)	0.0208 (14)	0.0207 (13)	−0.0047 (11)	0.0022 (11)	−0.0020 (11)
C23	0.0274 (15)	0.0274 (16)	0.0227 (14)	−0.0006 (12)	0.0053 (12)	−0.0015 (11)
C2	0.0235 (15)	0.0223 (15)	0.0270 (14)	0.0003 (11)	0.0022 (11)	0.0025 (11)
C9	0.0211 (14)	0.0197 (14)	0.0211 (13)	−0.0035 (11)	0.0024 (11)	0.0007 (11)
F1	0.0396 (10)	0.0612 (13)	0.0312 (9)	0.0285 (10)	0.0135 (8)	0.0136 (9)
C21	0.0363 (18)	0.053 (2)	0.0191 (14)	0.0089 (15)	0.0072 (13)	−0.0036 (14)
C4	0.0260 (15)	0.0247 (15)	0.0238 (14)	−0.0061 (12)	0.0053 (11)	−0.0075 (11)
C15	0.0266 (15)	0.0295 (16)	0.0183 (13)	0.0005 (12)	0.0056 (11)	0.0016 (11)
C3	0.0241 (15)	0.0194 (14)	0.0327 (15)	−0.0011 (12)	0.0040 (12)	−0.0060 (12)
C24	0.0288 (16)	0.0291 (16)	0.0197 (14)	0.0047 (12)	0.0060 (12)	0.0050 (12)
C1	0.0194 (13)	0.0198 (14)	0.0221 (13)	−0.0028 (11)	0.0049 (10)	0.0022 (11)
C22	0.0418 (19)	0.0403 (18)	0.0242 (15)	−0.0002 (15)	0.0126 (14)	0.0050 (13)
N1	0.0225 (12)	0.0183 (11)	0.0177 (11)	−0.0040 (9)	0.0027 (9)	−0.0010 (9)
C7	0.0201 (14)	0.0177 (13)	0.0191 (13)	−0.0059 (11)	0.0033 (10)	−0.0015 (10)
C18	0.0180 (13)	0.0255 (14)	0.0178 (13)	0.0031 (11)	0.0008 (10)	−0.0008 (11)
C16	0.0254 (14)	0.0182 (14)	0.0217 (13)	0.0018 (11)	0.0045 (11)	0.0000 (11)
N2	0.0251 (13)	0.0322 (14)	0.0197 (12)	0.0038 (11)	0.0039 (10)	0.0029 (11)
C25	0.051 (2)	0.0323 (18)	0.0257 (15)	−0.0007 (15)	0.0088 (14)	−0.0035 (13)
C17	0.0200 (14)	0.0198 (14)	0.0197 (13)	−0.0040 (11)	0.0028 (11)	−0.0018 (10)
C10	0.0194 (13)	0.0194 (13)	0.0180 (12)	−0.0048 (11)	0.0001 (10)	−0.0005 (10)
C6	0.0201 (14)	0.0178 (13)	0.0223 (13)	−0.0057 (11)	0.0036 (11)	−0.0015 (10)
C20	0.0320 (17)	0.0352 (17)	0.0266 (15)	0.0082 (14)	−0.0007 (12)	−0.0118 (13)
C19	0.0256 (15)	0.0268 (15)	0.0242 (14)	0.0040 (12)	0.0005 (11)	−0.0013 (12)
C11	0.0266 (15)	0.0208 (14)	0.0223 (14)	0.0011 (11)	0.0051 (11)	−0.0010 (11)
C8	0.0236 (14)	0.0211 (14)	0.0148 (12)	−0.0039 (11)	0.0030 (10)	0.0002 (10)
C12	0.0295 (15)	0.0282 (16)	0.0170 (13)	0.0004 (12)	0.0062 (11)	0.0009 (11)
C13	0.0260 (15)	0.0338 (17)	0.0222 (14)	0.0062 (13)	0.0011 (11)	0.0067 (12)
F2	0.0452 (11)	0.0492 (11)	0.0194 (8)	0.0183 (9)	0.0115 (8)	0.0097 (8)

Geometric parameters (Å, º) top

Pt1—C1	1.981 (3)	C3—H3	0.9300
Pt1—N1	2.046 (2)	C24—N2	1.139 (4)
Pt1—N2	2.106 (2)	C24—C25	1.456 (4)
Pt1—Cl1	2.3036 (9)	C1—C6	1.416 (4)
C14—F1	1.360 (3)	C22—H22	0.9300
C14—C15	1.371 (4)	N1—C17	1.359 (3)
C14—C13	1.372 (4)	N1—C7	1.369 (3)
C5—C4	1.393 (4)	C7—C8	1.397 (4)
C5—C6	1.399 (4)	C7—C6	1.456 (4)
C5—H5	0.9300	C18—C19	1.394 (4)
C23—C22	1.389 (4)	C18—C17	1.481 (4)
C23—C18	1.392 (4)	C16—C17	1.387 (4)
C23—H23	0.9300	C16—H16	0.9300
C2—C3	1.389 (4)	C25—H25A	0.9600
C2—C1	1.390 (4)	C25—H25B	0.9600
C2—H2	0.9300	C25—H25C	0.9600
C9—C8	1.387 (4)	C10—C11	1.405 (4)
C9—C16	1.393 (4)	C20—C19	1.387 (4)
C9—C10	1.487 (4)	C20—H20	0.9300
C21—C20	1.377 (5)	C19—H19	0.9300
C21—C22	1.385 (5)	C11—C12	1.369 (4)
C21—H21	0.9300	C11—H11	0.9300
C4—C3	1.387 (4)	C8—H8	0.9300
C4—H4	0.9300	C12—F2	1.364 (3)
C15—C10	1.402 (4)	C12—C13	1.382 (4)
C15—H15	0.9300	C13—H13	0.9300

C1—Pt1—N1	81.55 (10)	N1—C7—C8	120.9 (2)
C1—Pt1—N2	166.63 (10)	N1—C7—C6	114.4 (2)
N1—Pt1—N2	99.24 (9)	C8—C7—C6	124.7 (2)
C1—Pt1—Cl1	93.84 (8)	C23—C18—C19	119.2 (3)
N1—Pt1—Cl1	174.90 (6)	C23—C18—C17	119.7 (2)
N2—Pt1—Cl1	85.75 (7)	C19—C18—C17	121.0 (2)
F1—C14—C15	118.0 (2)	C17—C16—C9	121.3 (3)
F1—C14—C13	117.8 (2)	C17—C16—H16	119.4
C15—C14—C13	124.2 (3)	C9—C16—H16	119.4
C4—C5—C6	119.8 (3)	C24—N2—Pt1	168.0 (2)
C4—C5—H5	120.1	C24—C25—H25A	109.5
C6—C5—H5	120.1	C24—C25—H25B	109.5
C22—C23—C18	120.2 (3)	H25A—C25—H25B	109.5
C22—C23—H23	119.9	C24—C25—H25C	109.5
C18—C23—H23	119.9	H25A—C25—H25C	109.5
C3—C2—C1	121.2 (3)	H25B—C25—H25C	109.5
C3—C2—H2	119.4	N1—C17—C16	121.1 (2)
C1—C2—H2	119.4	N1—C17—C18	120.4 (2)
C8—C9—C16	116.8 (2)	C16—C17—C18	118.5 (2)
C8—C9—C10	121.5 (2)	C15—C10—C11	118.9 (2)
C16—C9—C10	121.7 (2)	C15—C10—C9	120.7 (2)
C20—C21—C22	119.6 (3)	C11—C10—C9	120.3 (2)
C20—C21—H21	120.2	C5—C6—C1	121.2 (3)
C22—C21—H21	120.2	C5—C6—C7	123.4 (2)
C3—C4—C5	119.2 (2)	C1—C6—C7	115.5 (2)
C3—C4—H4	120.4	C21—C20—C19	120.8 (3)
C5—C4—H4	120.4	C21—C20—H20	119.6
C14—C15—C10	118.7 (2)	C19—C20—H20	119.6
C14—C15—H15	120.6	C20—C19—C18	119.9 (3)
C10—C15—H15	120.6	C20—C19—H19	120.0
C4—C3—C2	121.0 (3)	C18—C19—H19	120.0
C4—C3—H3	119.5	C12—C11—C10	118.6 (3)
C2—C3—H3	119.5	C12—C11—H11	120.7
N2—C24—C25	179.2 (3)	C10—C11—H11	120.7
C2—C1—C6	117.5 (2)	C9—C8—C7	120.9 (2)
C2—C1—Pt1	128.8 (2)	C9—C8—H8	119.5
C6—C1—Pt1	113.04 (19)	C7—C8—H8	119.5
C21—C22—C23	120.3 (3)	F2—C12—C11	119.0 (2)
C21—C22—H22	119.9	F2—C12—C13	116.9 (2)
C23—C22—H22	119.9	C11—C12—C13	124.1 (2)
C17—N1—C7	118.7 (2)	C14—C13—C12	115.5 (3)
C17—N1—Pt1	127.75 (17)	C14—C13—H13	122.3
C7—N1—Pt1	113.46 (17)	C12—C13—H13	122.3

C6—C5—C4—C3	−2.9 (4)	C16—C9—C10—C15	21.0 (4)
F1—C14—C15—C10	178.6 (3)	C8—C9—C10—C11	21.4 (4)
C13—C14—C15—C10	−1.8 (5)	C16—C9—C10—C11	−159.8 (3)
C5—C4—C3—C2	3.3 (4)	C4—C5—C6—C1	−0.4 (4)
C1—C2—C3—C4	−0.2 (4)	C4—C5—C6—C7	−179.4 (2)
C3—C2—C1—C6	−3.0 (4)	C2—C1—C6—C5	3.3 (4)
C3—C2—C1—Pt1	166.9 (2)	Pt1—C1—C6—C5	−168.2 (2)
C20—C21—C22—C23	−1.7 (5)	C2—C1—C6—C7	−177.6 (2)
C18—C23—C22—C21	1.8 (5)	Pt1—C1—C6—C7	10.9 (3)
C17—N1—C7—C8	−4.1 (4)	N1—C7—C6—C5	178.7 (2)
Pt1—N1—C7—C8	172.12 (19)	C8—C7—C6—C5	−3.6 (4)
C17—N1—C7—C6	173.7 (2)	N1—C7—C6—C1	−0.4 (3)
Pt1—N1—C7—C6	−10.0 (3)	C8—C7—C6—C1	177.4 (2)
C22—C23—C18—C19	−0.4 (4)	C22—C21—C20—C19	0.1 (5)
C22—C23—C18—C17	175.2 (3)	C21—C20—C19—C18	1.3 (4)
C8—C9—C16—C17	−1.6 (4)	C23—C18—C19—C20	−1.2 (4)
C10—C9—C16—C17	179.6 (2)	C17—C18—C19—C20	−176.7 (3)
C7—N1—C17—C16	6.1 (4)	C15—C10—C11—C12	1.2 (4)
Pt1—N1—C17—C16	−169.5 (2)	C9—C10—C11—C12	−177.9 (2)
C7—N1—C17—C18	−170.9 (2)	C16—C9—C8—C7	3.6 (4)
Pt1—N1—C17—C18	13.5 (4)	C10—C9—C8—C7	−177.7 (2)
C9—C16—C17—N1	−3.3 (4)	N1—C7—C8—C9	−0.8 (4)
C9—C16—C17—C18	173.8 (2)	C6—C7—C8—C9	−178.4 (2)
C23—C18—C17—N1	53.1 (4)	C10—C11—C12—F2	179.4 (2)
C19—C18—C17—N1	−131.4 (3)	C10—C11—C12—C13	−1.4 (4)
C23—C18—C17—C16	−124.0 (3)	F1—C14—C13—C12	−178.7 (3)
C19—C18—C17—C16	51.5 (4)	C15—C14—C13—C12	1.7 (5)
C14—C15—C10—C11	0.3 (4)	F2—C12—C13—C14	179.2 (3)
C14—C15—C10—C9	179.4 (3)	C11—C12—C13—C14	−0.1 (5)
C8—C9—C10—C15	−157.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cl1ⁱ	0.93	2.77	3.545 (3)	142
C25—H25A···F1ⁱⁱ	0.96	2.42	3.202 (4)	138
C25—H25B···Cl1ⁱⁱⁱ	0.96	2.66	3.613 (3)	169

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

Funding information

This work was supported by the Undergraduate Research Training Program of Anhui University (award No. KYXL2017023) and the National Natural Science Foundation of China (award No. 51672002).

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