Synthesis, crystal structure and photophysical properties of chlorido­[2-(2′,6′-di­fluoro-2,3′-bipyri­din-6-yl-κN1)-6-(pyridin-2-yl­oxy-κN)phenyl-κC1]platinum(II)

Park, K.-M.; Moon, C.J.; Paek, S.; Kang, Y.

doi:10.1107/S2056989021000128

Synthesis, crystal structure and photophysical properties of chlorido[2-(2′,6′-difluoro-2,3′-bipyridin-6-yl-κN¹)-6-(pyridin-2-yloxy-κN)phenyl-κC¹]platinum(II)

K.-M. Park, C. J. Moon, S. Paek and Y. Kang

In the crystal of the title compound, which shows blue–green emission, the molecules are connected via C—H

Cl/F, halogen

π and weak π–π stacking interactions.

Keywords: crystal structure; 2,3′-bipyridine; platinum compound; luminescence; OLED.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989021000128/hb7960sup1.cif Contains datablocks I, New_Global_Publ_Block
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989021000128/hb7960Isup2.hkl Contains datablock I

CCDC reference: 2053861

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.007 Å
R factor = 0.028
wR factor = 0.067
Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         O1 Check
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         O2 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15      ..F1       .       2.56 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         10 Report
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.85A   From Pt1             1.66 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT012_ALERT_1_G N.O.K.   _shelx_res_checksum Found in CIF ......     Please Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.003 Degree
PLAT794_ALERT_5_G Tentative Bond Valency for Pt1       (II)      .       2.05 Info
PLAT794_ALERT_5_G Tentative Bond Valency for Pt2       (II)      .       2.03 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         56 Note

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

   2 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
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Chlorido[2-(2',6'-difluoro-2,3'-bipyridin-6-yl-κN¹)-6-(pyridin-2-yloxy-κN)phenyl-κC¹]platinum(II) top

Crystal data top

[Pt(C₂₁H₁₂F₂N₃O)Cl]	Z = 4
M_r = 590.88	F(000) = 1120
Triclinic, P1	D_x = 2.131 Mg m⁻³
a = 12.4924 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.5008 (9) Å	Cell parameters from 9258 reflections
c = 14.1163 (11) Å	θ = 2.6–28.3°
α = 74.498 (3)°	µ = 7.80 mm⁻¹
β = 73.401 (3)°	T = 173 K
γ = 61.954 (3)°	Block, yellow
V = 1841.3 (2) Å³	0.46 × 0.32 × 0.24 mm

Data collection top

Bruker APEXII CCD diffractometer	7667 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.045
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θ_max = 28.3°, θ_min = 1.5°
T_min = 0.233, T_max = 0.746	h = −16→16
34679 measured reflections	k = −15→16
9126 independent reflections	l = −18→18

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.067	w = 1/[σ²(F_o²) + (0.0327P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
9126 reflections	Δρ_max = 1.64 e Å⁻³
523 parameters	Δρ_min = −1.21 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	0.69646 (2)	0.61157 (2)	0.39509 (2)	0.03247 (5)
Pt2	0.88563 (2)	0.80611 (2)	0.10492 (2)	0.03240 (5)
Cl1	0.86494 (8)	0.44909 (8)	0.47237 (7)	0.0410 (2)
Cl2	1.05014 (8)	0.63393 (8)	0.02853 (7)	0.0413 (2)
F1	0.8999 (2)	0.1430 (2)	0.4219 (2)	0.0689 (7)
F2	1.2132 (2)	0.1920 (3)	0.1978 (2)	0.0730 (8)
F3	1.3562 (2)	0.6034 (2)	0.0774 (2)	0.0685 (7)
F4	1.3006 (3)	0.2977 (2)	0.3009 (2)	0.0711 (7)
O1	0.5471 (3)	0.9163 (2)	0.3614 (3)	0.0668 (9)
O2	0.5792 (2)	0.9597 (3)	0.1333 (3)	0.0674 (9)
N1	0.7262 (3)	0.7497 (3)	0.4159 (2)	0.0358 (7)
N2	0.6446 (3)	0.4930 (3)	0.3661 (2)	0.0340 (7)
N3	1.0540 (3)	0.1720 (3)	0.3099 (3)	0.0504 (9)
N4	0.7472 (3)	0.7748 (3)	0.0861 (2)	0.0358 (7)
N5	1.0042 (3)	0.8593 (3)	0.1331 (2)	0.0340 (7)
N6	1.3250 (3)	0.4527 (3)	0.1888 (3)	0.0479 (8)
C1	0.8297 (4)	0.7229 (4)	0.4491 (3)	0.0421 (9)
H1	0.8809	0.6389	0.4688	0.050*
C2	0.8652 (5)	0.8078 (4)	0.4562 (4)	0.0550 (11)
H2	0.9387	0.7833	0.4797	0.066*
C3	0.7916 (5)	0.9306 (4)	0.4283 (4)	0.0661 (13)
H3	0.8138	0.9921	0.4322	0.079*
C4	0.6870 (5)	0.9618 (4)	0.3953 (4)	0.0657 (13)
H4	0.6358	1.0455	0.3748	0.079*
C5	0.6559 (4)	0.8701 (4)	0.3920 (3)	0.0511 (11)
C6	0.4800 (4)	0.8536 (4)	0.3637 (3)	0.0505 (10)
C7	0.3573 (4)	0.9249 (4)	0.3571 (3)	0.0586 (12)
H7	0.3244	1.0117	0.3499	0.070*
C8	0.2835 (4)	0.8706 (4)	0.3610 (3)	0.0587 (12)
H8	0.1985	0.9199	0.3585	0.070*
C9	0.3308 (4)	0.7440 (4)	0.3685 (3)	0.0490 (10)
H9	0.2791	0.7059	0.3720	0.059*
C10	0.4556 (4)	0.6748 (4)	0.3706 (3)	0.0416 (9)
C11	0.5324 (4)	0.7272 (3)	0.3681 (3)	0.0393 (8)
C12	0.5184 (3)	0.5402 (3)	0.3718 (3)	0.0375 (8)
C13	0.4631 (4)	0.4677 (4)	0.3732 (3)	0.0459 (10)
H13	0.3762	0.5021	0.3785	0.055*
C14	0.5330 (4)	0.3454 (4)	0.3668 (3)	0.0498 (10)
H14	0.4949	0.2933	0.3719	0.060*
C15	0.6593 (4)	0.2998 (4)	0.3530 (3)	0.0463 (9)
H15	0.7091	0.2161	0.3457	0.056*
C16	0.7148 (4)	0.3742 (3)	0.3495 (3)	0.0370 (8)
C17	0.8482 (3)	0.3332 (3)	0.3148 (3)	0.0365 (8)
C18	0.9353 (4)	0.2176 (3)	0.3469 (3)	0.0461 (10)
C19	1.0912 (4)	0.2433 (4)	0.2383 (3)	0.0492 (10)
C20	1.0203 (4)	0.3602 (4)	0.1990 (3)	0.0475 (9)
H20	1.0544	0.4082	0.1473	0.057*
C21	0.8959 (4)	0.4040 (3)	0.2393 (3)	0.0426 (9)
H21	0.8418	0.4847	0.2146	0.051*
C22	0.7757 (3)	0.6672 (4)	0.0570 (3)	0.0408 (9)
H22	0.8606	0.6136	0.0403	0.049*
C23	0.6911 (4)	0.6315 (5)	0.0502 (4)	0.0566 (12)
H23	0.7162	0.5556	0.0294	0.068*
C24	0.5660 (4)	0.7100 (5)	0.0748 (4)	0.0658 (14)
H24	0.5042	0.6880	0.0715	0.079*
C25	0.5344 (4)	0.8173 (5)	0.1032 (4)	0.0655 (13)
H25	0.4499	0.8718	0.1202	0.079*
C26	0.6258 (4)	0.8477 (4)	0.1076 (3)	0.0500 (10)
C27	0.6426 (4)	1.0252 (4)	0.1338 (3)	0.0480 (10)
C28	0.5712 (4)	1.1484 (4)	0.1399 (3)	0.0576 (12)
H28	0.4841	1.1823	0.1463	0.069*
C29	0.6266 (4)	1.2206 (4)	0.1368 (3)	0.0589 (12)
H29	0.5775	1.3056	0.1394	0.071*
C30	0.7530 (4)	1.1732 (4)	0.1298 (3)	0.0507 (10)
H30	0.7910	1.2249	0.1261	0.061*
C31	0.8231 (4)	1.0476 (4)	0.1284 (3)	0.0398 (9)
C32	0.7694 (3)	0.9716 (3)	0.1304 (3)	0.0380 (8)
C33	0.9573 (4)	0.9852 (4)	0.1276 (3)	0.0398 (9)
C34	1.0291 (4)	1.0404 (4)	0.1256 (3)	0.0439 (9)
H34	0.9949	1.1272	0.1193	0.053*
C35	1.1513 (4)	0.9709 (4)	0.1327 (3)	0.0499 (10)
H35	1.2035	1.0087	0.1281	0.060*
C36	1.1962 (4)	0.8450 (4)	0.1465 (3)	0.0466 (9)
H36	1.2797	0.7955	0.1541	0.056*
C37	1.1221 (3)	0.7895 (4)	0.1496 (3)	0.0370 (8)
C38	1.1627 (3)	0.6569 (3)	0.1841 (3)	0.0349 (8)
C39	1.2793 (3)	0.5693 (4)	0.1529 (3)	0.0452 (10)
C40	1.2510 (4)	0.4174 (4)	0.2611 (3)	0.0494 (10)
C41	1.1313 (4)	0.4895 (4)	0.2994 (3)	0.0463 (9)
H41	1.0810	0.4570	0.3502	0.056*
C42	1.0885 (3)	0.6118 (4)	0.2596 (3)	0.0414 (9)
H42	1.0066	0.6665	0.2843	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.03777 (9)	0.02938 (8)	0.03200 (8)	−0.01344 (6)	−0.01039 (6)	−0.00506 (6)
Pt2	0.02768 (8)	0.03840 (9)	0.03250 (8)	−0.01276 (6)	−0.00509 (6)	−0.01087 (6)
Cl1	0.0438 (5)	0.0350 (4)	0.0486 (5)	−0.0142 (4)	−0.0198 (4)	−0.0065 (4)
Cl2	0.0340 (5)	0.0435 (5)	0.0498 (5)	−0.0123 (4)	−0.0076 (4)	−0.0212 (4)
F1	0.0752 (18)	0.0410 (13)	0.0822 (19)	−0.0289 (13)	−0.0188 (15)	0.0153 (13)
F2	0.0478 (15)	0.0675 (18)	0.093 (2)	−0.0155 (14)	−0.0027 (14)	−0.0253 (15)
F3	0.0387 (13)	0.0711 (17)	0.0841 (19)	−0.0261 (13)	0.0130 (12)	−0.0154 (14)
F4	0.0702 (18)	0.0477 (15)	0.0856 (19)	−0.0189 (14)	−0.0214 (15)	−0.0003 (14)
O1	0.071 (2)	0.0312 (15)	0.105 (3)	−0.0161 (15)	−0.047 (2)	0.0014 (16)
O2	0.0295 (15)	0.071 (2)	0.104 (3)	−0.0123 (15)	−0.0051 (15)	−0.0447 (19)
N1	0.0453 (18)	0.0280 (15)	0.0366 (16)	−0.0167 (14)	−0.0065 (13)	−0.0082 (12)
N2	0.0411 (17)	0.0318 (16)	0.0313 (16)	−0.0158 (14)	−0.0099 (13)	−0.0047 (12)
N3	0.050 (2)	0.0360 (18)	0.067 (2)	−0.0129 (17)	−0.0152 (18)	−0.0159 (17)
N4	0.0288 (15)	0.0432 (18)	0.0364 (16)	−0.0142 (14)	−0.0073 (12)	−0.0088 (14)
N5	0.0321 (16)	0.0387 (17)	0.0330 (16)	−0.0136 (14)	−0.0054 (12)	−0.0122 (13)
N6	0.0372 (18)	0.045 (2)	0.061 (2)	−0.0130 (16)	−0.0155 (17)	−0.0106 (17)
C1	0.048 (2)	0.042 (2)	0.045 (2)	−0.0228 (19)	−0.0103 (18)	−0.0106 (17)
C2	0.064 (3)	0.051 (3)	0.062 (3)	−0.030 (2)	−0.014 (2)	−0.015 (2)
C3	0.090 (4)	0.049 (3)	0.079 (3)	−0.040 (3)	−0.024 (3)	−0.012 (2)
C4	0.084 (3)	0.031 (2)	0.092 (4)	−0.022 (2)	−0.039 (3)	−0.006 (2)
C5	0.062 (3)	0.037 (2)	0.052 (3)	−0.015 (2)	−0.018 (2)	−0.0069 (19)
C6	0.056 (3)	0.037 (2)	0.053 (3)	−0.011 (2)	−0.021 (2)	−0.0040 (19)
C7	0.063 (3)	0.041 (2)	0.066 (3)	−0.006 (2)	−0.031 (2)	−0.008 (2)
C8	0.046 (2)	0.061 (3)	0.057 (3)	−0.008 (2)	−0.022 (2)	−0.006 (2)
C9	0.041 (2)	0.056 (3)	0.047 (2)	−0.011 (2)	−0.0166 (18)	−0.011 (2)
C10	0.045 (2)	0.045 (2)	0.034 (2)	−0.0149 (19)	−0.0134 (17)	−0.0064 (17)
C11	0.044 (2)	0.038 (2)	0.0312 (19)	−0.0135 (18)	−0.0126 (16)	−0.0006 (16)
C12	0.041 (2)	0.042 (2)	0.0297 (19)	−0.0163 (18)	−0.0118 (16)	−0.0026 (16)
C13	0.045 (2)	0.061 (3)	0.041 (2)	−0.025 (2)	−0.0128 (18)	−0.0124 (19)
C14	0.063 (3)	0.054 (3)	0.052 (2)	−0.038 (2)	−0.018 (2)	−0.007 (2)
C15	0.058 (3)	0.042 (2)	0.046 (2)	−0.025 (2)	−0.0131 (19)	−0.0092 (18)
C16	0.049 (2)	0.0316 (18)	0.0343 (19)	−0.0173 (17)	−0.0125 (16)	−0.0048 (15)
C17	0.045 (2)	0.0310 (18)	0.037 (2)	−0.0149 (17)	−0.0091 (16)	−0.0110 (16)
C18	0.055 (3)	0.034 (2)	0.053 (3)	−0.020 (2)	−0.012 (2)	−0.0076 (18)
C19	0.043 (2)	0.047 (2)	0.058 (3)	−0.013 (2)	−0.010 (2)	−0.022 (2)
C20	0.052 (2)	0.052 (2)	0.041 (2)	−0.026 (2)	−0.0040 (18)	−0.0090 (19)
C21	0.054 (2)	0.036 (2)	0.035 (2)	−0.0141 (18)	−0.0130 (17)	−0.0053 (16)
C22	0.0339 (19)	0.048 (2)	0.047 (2)	−0.0187 (18)	−0.0086 (16)	−0.0132 (18)
C23	0.051 (3)	0.067 (3)	0.065 (3)	−0.033 (2)	−0.011 (2)	−0.016 (2)
C24	0.042 (3)	0.094 (4)	0.081 (3)	−0.039 (3)	−0.010 (2)	−0.027 (3)
C25	0.032 (2)	0.081 (3)	0.091 (4)	−0.020 (2)	−0.008 (2)	−0.038 (3)
C26	0.036 (2)	0.064 (3)	0.052 (3)	−0.017 (2)	−0.0089 (18)	−0.020 (2)
C27	0.036 (2)	0.055 (3)	0.048 (2)	−0.011 (2)	−0.0038 (18)	−0.021 (2)
C28	0.039 (2)	0.063 (3)	0.064 (3)	−0.004 (2)	−0.011 (2)	−0.032 (2)
C29	0.055 (3)	0.045 (2)	0.060 (3)	−0.001 (2)	−0.010 (2)	−0.024 (2)
C30	0.058 (3)	0.044 (2)	0.045 (2)	−0.013 (2)	−0.008 (2)	−0.0184 (19)
C31	0.040 (2)	0.040 (2)	0.037 (2)	−0.0118 (18)	−0.0059 (16)	−0.0147 (17)
C32	0.035 (2)	0.042 (2)	0.0330 (19)	−0.0118 (17)	−0.0047 (15)	−0.0111 (16)
C33	0.042 (2)	0.043 (2)	0.033 (2)	−0.0153 (18)	0.0004 (16)	−0.0188 (17)
C34	0.052 (2)	0.042 (2)	0.040 (2)	−0.019 (2)	−0.0089 (18)	−0.0125 (17)
C35	0.053 (3)	0.060 (3)	0.055 (3)	−0.035 (2)	−0.0053 (19)	−0.019 (2)
C36	0.036 (2)	0.058 (3)	0.052 (2)	−0.021 (2)	−0.0093 (17)	−0.015 (2)
C37	0.036 (2)	0.047 (2)	0.0302 (19)	−0.0164 (18)	−0.0043 (15)	−0.0132 (16)
C38	0.0292 (18)	0.044 (2)	0.0349 (19)	−0.0143 (16)	−0.0083 (15)	−0.0107 (16)
C39	0.032 (2)	0.062 (3)	0.047 (2)	−0.025 (2)	−0.0054 (17)	−0.011 (2)
C40	0.050 (2)	0.045 (2)	0.058 (3)	−0.017 (2)	−0.022 (2)	−0.008 (2)
C41	0.050 (2)	0.055 (3)	0.035 (2)	−0.025 (2)	−0.0102 (18)	−0.0031 (18)
C42	0.035 (2)	0.053 (2)	0.034 (2)	−0.0157 (18)	−0.0054 (15)	−0.0114 (17)

Geometric parameters (Å, º) top

Pt1—C11	1.949 (4)	C12—C13	1.368 (5)
Pt1—N1	2.035 (3)	C13—C14	1.370 (6)
Pt1—N2	2.040 (3)	C13—H13	0.9500
Pt1—Cl1	2.4193 (8)	C14—C15	1.375 (6)
Pt2—C32	1.948 (4)	C14—H14	0.9500
Pt2—N4	2.042 (3)	C15—C16	1.381 (5)
Pt2—N5	2.049 (3)	C15—H15	0.9500
Pt2—Cl2	2.4154 (8)	C16—C17	1.465 (5)
F1—C18	1.334 (5)	C17—C21	1.380 (5)
F2—C19	1.356 (5)	C17—C18	1.389 (5)
F3—C39	1.341 (4)	C19—C20	1.363 (6)
F4—C40	1.347 (5)	C20—C21	1.379 (5)
O1—C5	1.354 (5)	C20—H20	0.9500
O1—C6	1.380 (5)	C21—H21	0.9500
O2—C26	1.347 (5)	C22—C23	1.360 (6)
O2—C27	1.385 (5)	C22—H22	0.9500
N1—C5	1.344 (5)	C23—C24	1.398 (6)
N1—C1	1.364 (5)	C23—H23	0.9500
N2—C16	1.369 (5)	C24—C25	1.348 (7)
N2—C12	1.385 (5)	C24—H24	0.9500
N3—C19	1.292 (6)	C25—C26	1.382 (6)
N3—C18	1.311 (5)	C25—H25	0.9500
N4—C26	1.344 (5)	C27—C28	1.382 (6)
N4—C22	1.366 (5)	C27—C32	1.391 (5)
N5—C37	1.365 (5)	C28—C29	1.357 (7)
N5—C33	1.386 (5)	C28—H28	0.9500
N6—C40	1.301 (6)	C29—C30	1.384 (6)
N6—C39	1.302 (5)	C29—H29	0.9500
C1—C2	1.364 (6)	C30—C31	1.395 (5)
C1—H1	0.9500	C30—H30	0.9500
C2—C3	1.383 (6)	C31—C32	1.389 (5)
C2—H2	0.9500	C31—C33	1.477 (5)
C3—C4	1.359 (7)	C33—C34	1.355 (5)
C3—H3	0.9500	C34—C35	1.374 (6)
C4—C5	1.388 (6)	C34—H34	0.9500
C4—H4	0.9500	C35—C36	1.378 (6)
C6—C7	1.380 (6)	C35—H35	0.9500
C6—C11	1.388 (5)	C36—C37	1.381 (5)
C7—C8	1.362 (7)	C36—H36	0.9500
C7—H7	0.9500	C37—C38	1.470 (5)
C8—C9	1.391 (6)	C38—C39	1.380 (5)
C8—H8	0.9500	C38—C42	1.386 (5)
C9—C10	1.387 (5)	C40—C41	1.369 (6)
C9—H9	0.9500	C41—C42	1.371 (5)
C10—C11	1.383 (6)	C41—H41	0.9500
C10—C12	1.482 (5)	C42—H42	0.9500

C11—Pt1—N1	90.92 (14)	C21—C17—C16	121.3 (3)
C11—Pt1—N2	80.86 (14)	C18—C17—C16	123.7 (4)
N1—Pt1—N2	171.61 (12)	N3—C18—F1	114.5 (4)
C11—Pt1—Cl1	163.28 (11)	N3—C18—C17	125.7 (4)
N1—Pt1—Cl1	94.81 (9)	F1—C18—C17	119.7 (4)
N2—Pt1—Cl1	93.56 (9)	N3—C19—F2	114.7 (4)
C32—Pt2—N4	90.87 (14)	N3—C19—C20	126.8 (4)
C32—Pt2—N5	80.98 (13)	F2—C19—C20	118.4 (4)
N4—Pt2—N5	171.56 (11)	C19—C20—C21	115.4 (4)
C32—Pt2—Cl2	163.13 (11)	C19—C20—H20	122.3
N4—Pt2—Cl2	94.78 (9)	C21—C20—H20	122.3
N5—Pt2—Cl2	93.65 (8)	C20—C21—C17	121.5 (4)
C5—O1—C6	127.3 (3)	C20—C21—H21	119.3
C26—O2—C27	128.0 (3)	C17—C21—H21	119.3
C5—N1—C1	114.8 (3)	C23—C22—N4	124.6 (4)
C5—N1—Pt1	125.2 (3)	C23—C22—H22	117.7
C1—N1—Pt1	119.8 (2)	N4—C22—H22	117.7
C16—N2—C12	117.5 (3)	C22—C23—C24	118.0 (4)
C16—N2—Pt1	129.2 (3)	C22—C23—H23	121.0
C12—N2—Pt1	113.1 (2)	C24—C23—H23	121.0
C19—N3—C18	115.8 (4)	C25—C24—C23	119.1 (4)
C26—N4—C22	115.1 (3)	C25—C24—H24	120.5
C26—N4—Pt2	125.5 (3)	C23—C24—H24	120.5
C22—N4—Pt2	119.2 (2)	C24—C25—C26	119.6 (4)
C37—N5—C33	117.7 (3)	C24—C25—H25	120.2
C37—N5—Pt2	129.0 (2)	C26—C25—H25	120.2
C33—N5—Pt2	113.1 (2)	N4—C26—O2	124.0 (4)
C40—N6—C39	115.3 (4)	N4—C26—C25	123.7 (4)
C2—C1—N1	124.8 (4)	O2—C26—C25	112.2 (4)
C2—C1—H1	117.6	C28—C27—O2	115.6 (4)
N1—C1—H1	117.6	C28—C27—C32	121.5 (4)
C1—C2—C3	118.4 (4)	O2—C27—C32	122.9 (4)
C1—C2—H2	120.8	C29—C28—C27	119.5 (4)
C3—C2—H2	120.8	C29—C28—H28	120.3
C4—C3—C2	118.9 (4)	C27—C28—H28	120.3
C4—C3—H3	120.5	C28—C29—C30	121.5 (4)
C2—C3—H3	120.5	C28—C29—H29	119.2
C3—C4—C5	119.3 (4)	C30—C29—H29	119.2
C3—C4—H4	120.4	C29—C30—C31	118.4 (4)
C5—C4—H4	120.4	C29—C30—H30	120.8
N1—C5—O1	124.2 (4)	C31—C30—H30	120.8
N1—C5—C4	123.8 (4)	C32—C31—C30	121.4 (4)
O1—C5—C4	112.0 (4)	C32—C31—C33	115.2 (3)
O1—C6—C7	115.9 (4)	C30—C31—C33	123.3 (4)
O1—C6—C11	122.8 (4)	C31—C32—C27	117.6 (4)
C7—C6—C11	121.3 (4)	C31—C32—Pt2	114.9 (3)
C8—C7—C6	119.9 (4)	C27—C32—Pt2	126.6 (3)
C8—C7—H7	120.1	C34—C33—N5	122.0 (4)
C6—C7—H7	120.1	C34—C33—C31	125.6 (4)
C7—C8—C9	120.9 (4)	N5—C33—C31	112.4 (3)
C7—C8—H8	119.5	C33—C34—C35	120.1 (4)
C9—C8—H8	119.5	C33—C34—H34	120.0
C10—C9—C8	118.0 (4)	C35—C34—H34	120.0
C10—C9—H9	121.0	C34—C35—C36	118.3 (4)
C8—C9—H9	121.0	C34—C35—H35	120.8
C11—C10—C9	122.3 (4)	C36—C35—H35	120.8
C11—C10—C12	114.5 (3)	C35—C36—C37	121.1 (4)
C9—C10—C12	123.1 (4)	C35—C36—H36	119.4
C10—C11—C6	117.4 (4)	C37—C36—H36	119.4
C10—C11—Pt1	115.3 (3)	N5—C37—C36	120.1 (4)
C6—C11—Pt1	126.4 (3)	N5—C37—C38	119.0 (3)
C13—C12—N2	121.7 (4)	C36—C37—C38	120.3 (3)
C13—C12—C10	125.7 (4)	C39—C38—C42	114.6 (3)
N2—C12—C10	112.5 (3)	C39—C38—C37	124.0 (3)
C12—C13—C14	120.2 (4)	C42—C38—C37	121.1 (3)
C12—C13—H13	119.9	N6—C39—F3	114.3 (4)
C14—C13—H13	119.9	N6—C39—C38	126.7 (4)
C13—C14—C15	118.6 (4)	F3—C39—C38	118.9 (4)
C13—C14—H14	120.7	N6—C40—F4	115.0 (4)
C15—C14—H14	120.7	N6—C40—C41	126.4 (4)
C14—C15—C16	120.9 (4)	F4—C40—C41	118.6 (4)
C14—C15—H15	119.6	C40—C41—C42	115.7 (4)
C16—C15—H15	119.6	C40—C41—H41	122.1
N2—C16—C15	120.5 (4)	C42—C41—H41	122.1
N2—C16—C17	118.4 (3)	C41—C42—C38	121.2 (4)
C15—C16—C17	120.5 (3)	C41—C42—H42	119.4
C21—C17—C18	114.7 (4)	C38—C42—H42	119.4

C5—N1—C1—C2	−1.9 (6)	C26—N4—C22—C23	−0.8 (6)
Pt1—N1—C1—C2	173.2 (3)	Pt2—N4—C22—C23	174.2 (3)
N1—C1—C2—C3	0.3 (7)	N4—C22—C23—C24	−0.1 (7)
C1—C2—C3—C4	0.2 (7)	C22—C23—C24—C25	0.5 (8)
C2—C3—C4—C5	1.0 (8)	C23—C24—C25—C26	0.0 (8)
C1—N1—C5—O1	−177.3 (4)	C22—N4—C26—O2	−176.9 (4)
Pt1—N1—C5—O1	8.0 (6)	Pt2—N4—C26—O2	8.5 (6)
C1—N1—C5—C4	3.2 (6)	C22—N4—C26—C25	1.3 (6)
Pt1—N1—C5—C4	−171.6 (4)	Pt2—N4—C26—C25	−173.3 (4)
C6—O1—C5—N1	10.8 (7)	C27—O2—C26—N4	6.4 (7)
C6—O1—C5—C4	−169.6 (4)	C27—O2—C26—C25	−172.0 (4)
C3—C4—C5—N1	−2.9 (8)	C24—C25—C26—N4	−0.9 (8)
C3—C4—C5—O1	177.5 (5)	C24—C25—C26—O2	177.5 (5)
C5—O1—C6—C7	161.3 (4)	C26—O2—C27—C28	165.0 (4)
C5—O1—C6—C11	−21.3 (7)	C26—O2—C27—C32	−16.3 (7)
O1—C6—C7—C8	−178.6 (4)	O2—C27—C28—C29	−177.4 (4)
C11—C6—C7—C8	4.0 (7)	C32—C27—C28—C29	3.9 (7)
C6—C7—C8—C9	−2.0 (7)	C27—C28—C29—C30	−1.5 (7)
C7—C8—C9—C10	−0.8 (7)	C28—C29—C30—C31	−1.5 (7)
C8—C9—C10—C11	1.7 (6)	C29—C30—C31—C32	2.1 (6)
C8—C9—C10—C12	−176.0 (4)	C29—C30—C31—C33	−176.0 (4)
C9—C10—C11—C6	0.2 (6)	C30—C31—C32—C27	0.1 (6)
C12—C10—C11—C6	178.1 (3)	C33—C31—C32—C27	178.4 (3)
C9—C10—C11—Pt1	169.8 (3)	C30—C31—C32—Pt2	169.9 (3)
C12—C10—C11—Pt1	−12.4 (4)	C33—C31—C32—Pt2	−11.8 (4)
O1—C6—C11—C10	179.7 (4)	C28—C27—C32—C31	−3.2 (6)
C7—C6—C11—C10	−3.1 (6)	O2—C27—C32—C31	178.2 (4)
O1—C6—C11—Pt1	11.4 (6)	C28—C27—C32—Pt2	−171.7 (3)
C7—C6—C11—Pt1	−171.3 (3)	O2—C27—C32—Pt2	9.7 (6)
C16—N2—C12—C13	7.8 (5)	C37—N5—C33—C34	8.4 (5)
Pt1—N2—C12—C13	−167.8 (3)	Pt2—N5—C33—C34	−167.7 (3)
C16—N2—C12—C10	−169.1 (3)	C37—N5—C33—C31	−169.4 (3)
Pt1—N2—C12—C10	15.3 (4)	Pt2—N5—C33—C31	14.5 (4)
C11—C10—C12—C13	−179.3 (4)	C32—C31—C33—C34	179.9 (4)
C9—C10—C12—C13	−1.5 (6)	C30—C31—C33—C34	−1.8 (6)
C11—C10—C12—N2	−2.5 (5)	C32—C31—C33—N5	−2.3 (5)
C9—C10—C12—N2	175.3 (3)	C30—C31—C33—N5	175.9 (3)
N2—C12—C13—C14	−1.3 (6)	N5—C33—C34—C35	−2.4 (6)
C10—C12—C13—C14	175.2 (4)	C31—C33—C34—C35	175.1 (4)
C12—C13—C14—C15	−4.0 (6)	C33—C34—C35—C36	−3.1 (6)
C13—C14—C15—C16	2.6 (6)	C34—C35—C36—C37	2.4 (6)
C12—N2—C16—C15	−9.2 (5)	C33—N5—C37—C36	−8.9 (5)
Pt1—N2—C16—C15	165.6 (3)	Pt2—N5—C37—C36	166.4 (3)
C12—N2—C16—C17	162.7 (3)	C33—N5—C37—C38	162.7 (3)
Pt1—N2—C16—C17	−22.5 (5)	Pt2—N5—C37—C38	−21.9 (5)
C14—C15—C16—N2	4.2 (6)	C35—C36—C37—N5	3.8 (6)
C14—C15—C16—C17	−167.5 (4)	C35—C36—C37—C38	−167.8 (4)
N2—C16—C17—C21	−45.1 (5)	N5—C37—C38—C39	142.1 (4)
C15—C16—C17—C21	126.7 (4)	C36—C37—C38—C39	−46.3 (5)
N2—C16—C17—C18	141.4 (4)	N5—C37—C38—C42	−44.8 (5)
C15—C16—C17—C18	−46.8 (5)	C36—C37—C38—C42	126.8 (4)
C19—N3—C18—F1	−178.8 (4)	C40—N6—C39—F3	−178.8 (3)
C19—N3—C18—C17	1.0 (6)	C40—N6—C39—C38	0.3 (6)
C21—C17—C18—N3	−2.0 (6)	C42—C38—C39—N6	−1.7 (6)
C16—C17—C18—N3	171.9 (4)	C37—C38—C39—N6	171.7 (4)
C21—C17—C18—F1	177.7 (3)	C42—C38—C39—F3	177.4 (3)
C16—C17—C18—F1	−8.4 (6)	C37—C38—C39—F3	−9.2 (5)
C18—N3—C19—F2	−176.8 (3)	C39—N6—C40—F4	−177.1 (3)
C18—N3—C19—C20	1.0 (6)	C39—N6—C40—C41	2.3 (6)
N3—C19—C20—C21	−1.7 (6)	N6—C40—C41—C42	−3.1 (6)
F2—C19—C20—C21	176.1 (3)	F4—C40—C41—C42	176.4 (3)
C19—C20—C21—C17	0.4 (5)	C40—C41—C42—C38	1.3 (5)
C18—C17—C21—C20	1.2 (5)	C39—C38—C42—C41	0.8 (5)
C16—C17—C21—C20	−172.8 (3)	C37—C38—C42—C41	−172.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1	0.95	2.46	3.175 (4)	132
C3—H3···F1ⁱ	0.95	2.53	3.474 (5)	172
C15—H15···F1	0.95	2.56	2.989 (5)	108
C22—H22···Cl2	0.95	2.45	3.170 (4)	132
C23—H23···Cl2ⁱⁱ	0.95	2.82	3.540 (5)	133
C24—H24···F3ⁱⁱⁱ	0.95	2.50	3.443 (5)	172
C36—H36···F3	0.95	2.55	2.975 (5)	108
C41—H41···Cl1	0.95	2.79	3.684 (4)	158

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

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Synthesis, crystal structure and photophysical properties of chlorido­[2-(2′,6′-di­fluoro-2,3′-bipyri­din-6-yl-κN1)-6-(pyridin-2-yl­oxy-κN)phenyl-κC1]platinum(II)

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Synthesis, crystal structure and photophysical properties of chlorido[2-(2′,6′-difluoro-2,3′-bipyridin-6-yl-κN¹)-6-(pyridin-2-yloxy-κN)phenyl-κC¹]platinum(II)