Synthesis, crystal structure and Hirshfeld surface analysis of [bis­(di­phenyl­phosphan­yl)methane-κP]chloridobis­[2-(pyridin-2-yl)phenyl-κ2N,C1]iridium(III)

Klaimanee, E.; Sangwisut, P.; Saithong, S.; Leesakul, N.

doi:10.1107/S2056989021000955

Synthesis, crystal structure and Hirshfeld surface analysis of [bis(diphenylphosphanyl)methane-κP]chloridobis[2-(pyridin-2-yl)phenyl-κ²N,C¹]iridium(III)

E. Klaimanee, P. Sangwisut, S. Saithong and N. Leesakul

The title Ir^III complex was synthesized from the substitution reaction between the (ppy)₂Ir(μ-Cl)₂Ir(ppy)₂ (ppy = deprotonated 2-phenylpyridine, C₁₁H₈N⁻) dimer and 1,1-bis(diphenylphosphanyl)methane (dppm, C₂₅H₂₂P₂) under an argon gas atmosphere. The Ir^III atom is coordinated by two C,N-bidentate ppy anions, a unidentate dppm ligand and a chloride anion in a distorted octahedral IrC₂N₂PCl arrangement.

Keywords: crystal structure; iridium; 2-phenylpyridine; diphenylphosphanylmethane.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989021000955/hb7961sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989021000955/hb7961Isup2.hkl Contains datablock I
	MDL mol file https://doi.org/10.1107/S2056989021000955/hb7961Isup3.mol Supplementary material

CCDC reference: 2058995

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.026
wR factor = 0.062
Data-to-parameter ratio = 19.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.77 Report
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C38 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H30      ..CL1      .       2.84 Ang.

Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ir1      --Cl1      .        5.0 s.u.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 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
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: ShelXle (Hübschle et al., 2011), SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012) and publCIF (Westrip, 2010).

[Bis(diphenylphosphanyl)methane-κP]chloridobis[2-(pyridin-2-yl)phenyl-κ²N,C¹]iridium(III) top

Crystal data top

[Ir(C₁₁H₈N)₂Cl(C₂₅H₂₂P₂)]	F(000) = 1832
M_r = 920.38	D_x = 1.574 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.4506 (5) Å	Cell parameters from 9441 reflections
b = 15.4490 (5) Å	θ = 2.3–25.6°
c = 17.8532 (6) Å	µ = 3.63 mm⁻¹
β = 103.044 (1)°	T = 293 K
V = 3882.8 (2) Å³	Block, light yellow
Z = 4	0.19 × 0.09 × 0.06 mm

Data collection top

Bruker APEX CCD area-detector diffractometer	9248 independent reflections
Radiation source: fine-focus sealed tube	7758 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Frames, each covering 0.3 ° in ω scans	θ_max = 27.9°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −19→18
T_min = 0.800, T_max = 1.000	k = −20→20
35153 measured reflections	l = −23→23

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.062	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0298P)² + 0.328P] where P = (F_o² + 2F_c²)/3
9248 reflections	(Δ/σ)_max = 0.004
478 parameters	Δρ_max = 0.90 e Å⁻³
0 restraints	Δρ_min = −0.32 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
Ir1	0.68717 (2)	0.18203 (2)	0.91417 (2)	0.02951 (4)
Cl1	0.53215 (5)	0.24293 (5)	0.92683 (4)	0.04323 (17)
P1	0.76225 (5)	0.28142 (5)	1.01468 (4)	0.03235 (16)
P2	0.76117 (6)	0.48320 (5)	1.05116 (4)	0.03587 (17)
N1	0.71230 (16)	0.27466 (14)	0.83889 (12)	0.0322 (5)
N2	0.66418 (17)	0.07508 (14)	0.97668 (13)	0.0345 (5)
C1	0.6505 (2)	0.33752 (19)	0.80720 (17)	0.0414 (7)
H1	0.5898	0.3378	0.8167	0.050*
C2	0.6752 (3)	0.4012 (2)	0.76128 (18)	0.0492 (8)
H2	0.6313	0.4433	0.7395	0.059*
C3	0.7646 (3)	0.4020 (2)	0.74807 (19)	0.0528 (9)
H3	0.7830	0.4458	0.7187	0.063*
C4	0.8269 (3)	0.3377 (2)	0.77858 (18)	0.0466 (8)
H4	0.8880	0.3380	0.7700	0.056*
C5	0.7996 (2)	0.27145 (18)	0.82245 (15)	0.0353 (6)
C6	0.8552 (2)	0.19571 (18)	0.85264 (17)	0.0374 (7)
C7	0.9445 (2)	0.1771 (2)	0.8388 (2)	0.0494 (8)
H7	0.9729	0.2159	0.8111	0.059*
C8	0.9905 (3)	0.1019 (2)	0.8659 (2)	0.0575 (9)
H8	1.0506	0.0901	0.8577	0.069*
C9	0.9467 (3)	0.0438 (2)	0.9055 (2)	0.0556 (9)
H9	0.9766	−0.0082	0.9224	0.067*
C10	0.8589 (2)	0.0618 (2)	0.92042 (18)	0.0449 (7)
H10	0.8312	0.0217	0.9474	0.054*
C11	0.8109 (2)	0.13846 (18)	0.89610 (15)	0.0338 (6)
C12	0.7031 (2)	0.06046 (19)	1.05128 (17)	0.0469 (8)
H12	0.7442	0.1017	1.0785	0.056*
C13	0.6849 (3)	−0.0130 (2)	1.0891 (2)	0.0598 (10)
H13	0.7127	−0.0209	1.1409	0.072*
C14	0.6251 (3)	−0.0741 (2)	1.0492 (2)	0.0656 (11)
H14	0.6112	−0.1240	1.0736	0.079*
C15	0.5859 (3)	−0.0609 (2)	0.9727 (2)	0.0543 (9)
H15	0.5446	−0.1019	0.9453	0.065*
C16	0.6071 (2)	0.01343 (18)	0.93549 (17)	0.0373 (6)
C17	0.5754 (2)	0.03060 (18)	0.85349 (16)	0.0366 (6)
C18	0.5151 (2)	−0.0240 (2)	0.80214 (19)	0.0457 (7)
H18	0.4890	−0.0725	0.8203	0.055*
C19	0.4945 (2)	−0.0059 (2)	0.72503 (19)	0.0520 (8)
H19	0.4546	−0.0424	0.6907	0.062*
C20	0.5328 (2)	0.0662 (2)	0.69845 (18)	0.0488 (8)
H20	0.5194	0.0778	0.6460	0.059*
C21	0.5910 (2)	0.1216 (2)	0.74885 (16)	0.0409 (7)
H21	0.6159	0.1701	0.7296	0.049*
C22	0.61342 (19)	0.10635 (17)	0.82804 (15)	0.0324 (6)
C23	0.8897 (2)	0.2899 (2)	1.02168 (16)	0.0381 (7)
C24	0.9480 (2)	0.2230 (2)	1.0551 (2)	0.0531 (8)
H24	0.9226	0.1784	1.0793	0.064*
C25	1.0427 (3)	0.2207 (3)	1.0535 (2)	0.0675 (11)
H25	1.0807	0.1751	1.0767	0.081*
C26	1.0814 (3)	0.2856 (3)	1.0178 (3)	0.0708 (12)
H26	1.1452	0.2839	1.0160	0.085*
C27	1.0251 (3)	0.3526 (3)	0.9848 (2)	0.0621 (10)
H27	1.0513	0.3969	0.9610	0.074*
C28	0.9301 (2)	0.3557 (2)	0.98620 (18)	0.0460 (7)
H28	0.8929	0.4019	0.9634	0.055*
C29	0.7500 (2)	0.27335 (18)	1.11445 (16)	0.0388 (7)
C30	0.6630 (3)	0.2510 (2)	1.12801 (19)	0.0529 (8)
H30	0.6141	0.2342	1.0872	0.063*
C31	0.6477 (3)	0.2534 (3)	1.2018 (2)	0.0694 (11)
H31	0.5884	0.2392	1.2104	0.083*
C32	0.7209 (4)	0.2769 (3)	1.2625 (2)	0.0792 (13)
H32	0.7108	0.2784	1.3121	0.095*
C33	0.8081 (4)	0.2980 (3)	1.2500 (2)	0.0743 (13)
H33	0.8572	0.3133	1.2912	0.089*
C34	0.8234 (3)	0.2965 (2)	1.17625 (19)	0.0551 (9)
H34	0.8827	0.3110	1.1679	0.066*
C35	0.7142 (2)	0.38963 (17)	0.98911 (16)	0.0381 (7)
H35A	0.6463	0.3870	0.9857	0.046*
H35B	0.7227	0.4023	0.9379	0.046*
C36	0.6829 (2)	0.49398 (19)	1.11822 (17)	0.0395 (7)
C37	0.5910 (3)	0.4657 (2)	1.1068 (2)	0.0625 (10)
H37	0.5653	0.4332	1.0632	0.075*
C38	0.5354 (3)	0.4842 (3)	1.1587 (3)	0.0831 (14)
H38	0.4734	0.4636	1.1504	0.100*
C39	0.5727 (3)	0.5334 (3)	1.2227 (2)	0.0721 (12)
H39	0.5361	0.5458	1.2580	0.086*
C40	0.6627 (3)	0.5638 (3)	1.2342 (2)	0.0699 (12)
H40	0.6869	0.5988	1.2764	0.084*
C41	0.7188 (3)	0.5429 (2)	1.18332 (19)	0.0565 (9)
H41	0.7815	0.5619	1.1930	0.068*
C42	0.7121 (2)	0.56941 (18)	0.98220 (17)	0.0383 (7)
C43	0.6538 (3)	0.6345 (2)	0.9985 (2)	0.0520 (8)
H43	0.6357	0.6344	1.0453	0.062*
C44	0.6223 (3)	0.6995 (2)	0.9458 (2)	0.0659 (11)
H44	0.5827	0.7424	0.9574	0.079*
C45	0.6479 (3)	0.7019 (3)	0.8779 (2)	0.0673 (11)
H45	0.6269	0.7467	0.8434	0.081*
C46	0.7056 (3)	0.6376 (3)	0.8596 (2)	0.0594 (10)
H46	0.7224	0.6381	0.8123	0.071*
C47	0.7380 (2)	0.5729 (2)	0.91164 (18)	0.0468 (8)
H47	0.7780	0.5306	0.8996	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ir1	0.03490 (7)	0.02715 (6)	0.02633 (6)	−0.00467 (4)	0.00662 (4)	−0.00016 (4)
Cl1	0.0386 (4)	0.0438 (4)	0.0497 (4)	−0.0044 (3)	0.0150 (3)	−0.0041 (3)
P1	0.0393 (4)	0.0284 (3)	0.0293 (4)	−0.0065 (3)	0.0075 (3)	−0.0017 (3)
P2	0.0401 (4)	0.0312 (4)	0.0358 (4)	−0.0056 (3)	0.0074 (3)	−0.0042 (3)
N1	0.0393 (13)	0.0303 (12)	0.0270 (11)	−0.0046 (10)	0.0074 (10)	0.0011 (9)
N2	0.0420 (14)	0.0295 (12)	0.0320 (12)	−0.0061 (10)	0.0085 (11)	0.0011 (10)
C1	0.0457 (18)	0.0408 (17)	0.0376 (16)	0.0004 (13)	0.0090 (14)	0.0047 (13)
C2	0.063 (2)	0.0413 (18)	0.0418 (17)	0.0032 (16)	0.0096 (16)	0.0115 (14)
C3	0.072 (2)	0.0458 (18)	0.0463 (19)	−0.0085 (17)	0.0247 (18)	0.0100 (15)
C4	0.053 (2)	0.0519 (19)	0.0410 (17)	−0.0136 (15)	0.0233 (16)	−0.0014 (14)
C5	0.0417 (17)	0.0379 (16)	0.0279 (13)	−0.0059 (12)	0.0110 (12)	−0.0045 (12)
C6	0.0394 (16)	0.0397 (16)	0.0334 (15)	−0.0049 (12)	0.0092 (13)	−0.0067 (12)
C7	0.0446 (19)	0.059 (2)	0.0473 (19)	−0.0043 (16)	0.0167 (16)	−0.0086 (16)
C8	0.047 (2)	0.069 (2)	0.057 (2)	0.0124 (18)	0.0130 (17)	−0.0148 (19)
C9	0.057 (2)	0.050 (2)	0.055 (2)	0.0152 (17)	0.0033 (18)	−0.0123 (17)
C10	0.0518 (19)	0.0372 (17)	0.0446 (17)	0.0032 (14)	0.0089 (15)	−0.0021 (13)
C11	0.0378 (16)	0.0347 (15)	0.0274 (13)	−0.0005 (12)	0.0039 (12)	−0.0074 (11)
C12	0.067 (2)	0.0370 (17)	0.0339 (15)	−0.0143 (15)	0.0066 (15)	0.0024 (13)
C13	0.088 (3)	0.048 (2)	0.0401 (18)	−0.0137 (19)	0.0080 (18)	0.0123 (15)
C14	0.090 (3)	0.0412 (19)	0.064 (2)	−0.0216 (19)	0.014 (2)	0.0167 (17)
C15	0.068 (2)	0.0337 (17)	0.057 (2)	−0.0173 (16)	0.0066 (18)	0.0020 (15)
C16	0.0403 (16)	0.0297 (14)	0.0410 (16)	−0.0047 (12)	0.0072 (13)	−0.0019 (12)
C17	0.0378 (16)	0.0342 (15)	0.0379 (15)	−0.0024 (12)	0.0084 (13)	−0.0078 (12)
C18	0.0412 (17)	0.0392 (17)	0.055 (2)	−0.0065 (13)	0.0065 (15)	−0.0099 (14)
C19	0.0437 (19)	0.054 (2)	0.051 (2)	−0.0006 (16)	−0.0045 (16)	−0.0211 (16)
C20	0.0482 (19)	0.059 (2)	0.0335 (16)	0.0087 (16)	−0.0022 (14)	−0.0101 (15)
C21	0.0437 (17)	0.0437 (17)	0.0348 (15)	0.0045 (13)	0.0075 (14)	0.0008 (13)
C22	0.0303 (14)	0.0344 (14)	0.0319 (14)	0.0002 (11)	0.0057 (12)	−0.0064 (11)
C23	0.0407 (17)	0.0386 (15)	0.0343 (15)	−0.0089 (13)	0.0071 (13)	−0.0098 (12)
C24	0.049 (2)	0.0446 (19)	0.062 (2)	−0.0051 (16)	0.0060 (17)	−0.0013 (16)
C25	0.046 (2)	0.065 (3)	0.083 (3)	0.0051 (19)	−0.001 (2)	−0.011 (2)
C26	0.042 (2)	0.079 (3)	0.093 (3)	−0.014 (2)	0.018 (2)	−0.027 (3)
C27	0.057 (2)	0.071 (3)	0.065 (2)	−0.027 (2)	0.026 (2)	−0.018 (2)
C28	0.0501 (19)	0.0464 (18)	0.0431 (17)	−0.0130 (15)	0.0137 (15)	−0.0107 (14)
C29	0.0549 (19)	0.0316 (15)	0.0297 (14)	−0.0039 (13)	0.0093 (14)	−0.0023 (12)
C30	0.058 (2)	0.060 (2)	0.0440 (18)	−0.0061 (17)	0.0199 (17)	−0.0005 (16)
C31	0.082 (3)	0.076 (3)	0.062 (2)	−0.003 (2)	0.039 (2)	0.001 (2)
C32	0.116 (4)	0.089 (3)	0.041 (2)	0.001 (3)	0.034 (3)	−0.004 (2)
C33	0.101 (4)	0.086 (3)	0.0325 (19)	−0.008 (3)	0.006 (2)	−0.0113 (19)
C34	0.064 (2)	0.059 (2)	0.0387 (18)	−0.0119 (18)	0.0044 (17)	−0.0041 (15)
C35	0.0490 (18)	0.0304 (14)	0.0326 (14)	−0.0048 (13)	0.0044 (13)	−0.0031 (12)
C36	0.0453 (18)	0.0354 (15)	0.0380 (16)	0.0017 (13)	0.0100 (14)	0.0043 (13)
C37	0.059 (2)	0.058 (2)	0.075 (3)	−0.0176 (18)	0.023 (2)	−0.0163 (19)
C38	0.063 (3)	0.078 (3)	0.126 (4)	−0.016 (2)	0.057 (3)	−0.009 (3)
C39	0.080 (3)	0.081 (3)	0.068 (3)	0.014 (2)	0.042 (2)	0.018 (2)
C40	0.075 (3)	0.094 (3)	0.0402 (19)	0.023 (2)	0.0102 (19)	−0.005 (2)
C41	0.048 (2)	0.077 (2)	0.0423 (18)	0.0061 (18)	0.0049 (16)	−0.0139 (17)
C42	0.0420 (17)	0.0328 (15)	0.0411 (16)	−0.0066 (12)	0.0113 (14)	−0.0014 (12)
C43	0.069 (2)	0.0363 (17)	0.057 (2)	0.0033 (16)	0.0286 (18)	0.0051 (15)
C44	0.076 (3)	0.049 (2)	0.079 (3)	0.0178 (19)	0.032 (2)	0.0156 (19)
C45	0.072 (3)	0.064 (2)	0.071 (3)	0.013 (2)	0.026 (2)	0.034 (2)
C46	0.063 (2)	0.067 (2)	0.051 (2)	−0.007 (2)	0.0206 (18)	0.0163 (18)
C47	0.050 (2)	0.0455 (18)	0.0477 (19)	−0.0042 (15)	0.0173 (16)	0.0002 (14)

Geometric parameters (Å, º) top

Ir1—C11	2.004 (3)	C20—C21	1.381 (4)
Ir1—C22	2.032 (3)	C20—H20	0.9300
Ir1—N1	2.051 (2)	C21—C22	1.397 (4)
Ir1—N2	2.062 (2)	C21—H21	0.9300
Ir1—P1	2.4241 (7)	C23—C24	1.381 (5)
Ir1—Cl1	2.4866 (8)	C23—C28	1.394 (4)
P1—C23	1.822 (3)	C24—C25	1.377 (5)
P1—C35	1.828 (3)	C24—H24	0.9300
P1—C29	1.834 (3)	C25—C26	1.373 (6)
P2—C36	1.830 (3)	C25—H25	0.9300
P2—C42	1.844 (3)	C26—C27	1.365 (6)
P2—C35	1.854 (3)	C26—H26	0.9300
N1—C1	1.354 (4)	C27—C28	1.380 (5)
N1—C5	1.360 (4)	C27—H27	0.9300
N2—C12	1.343 (4)	C28—H28	0.9300
N2—C16	1.362 (3)	C29—C30	1.376 (4)
C1—C2	1.378 (4)	C29—C34	1.394 (4)
C1—H1	0.9300	C30—C31	1.384 (5)
C2—C3	1.365 (5)	C30—H30	0.9300
C2—H2	0.9300	C31—C32	1.381 (6)
C3—C4	1.369 (5)	C31—H31	0.9300
C3—H3	0.9300	C32—C33	1.367 (6)
C4—C5	1.398 (4)	C32—H32	0.9300
C4—H4	0.9300	C33—C34	1.384 (5)
C5—C6	1.453 (4)	C33—H33	0.9300
C6—C7	1.397 (4)	C34—H34	0.9300
C6—C11	1.421 (4)	C35—H35A	0.9700
C7—C8	1.372 (5)	C35—H35B	0.9700
C7—H7	0.9300	C36—C37	1.369 (4)
C8—C9	1.382 (5)	C36—C41	1.385 (4)
C8—H8	0.9300	C37—C38	1.387 (5)
C9—C10	1.382 (5)	C37—H37	0.9300
C9—H9	0.9300	C38—C39	1.376 (6)
C10—C11	1.391 (4)	C38—H38	0.9300
C10—H10	0.9300	C39—C40	1.353 (6)
C12—C13	1.376 (4)	C39—H39	0.9300
C12—H12	0.9300	C40—C41	1.386 (5)
C13—C14	1.367 (5)	C40—H40	0.9300
C13—H13	0.9300	C41—H41	0.9300
C14—C15	1.370 (5)	C42—C43	1.384 (4)
C14—H14	0.9300	C42—C47	1.394 (4)
C15—C16	1.395 (4)	C43—C44	1.382 (5)
C15—H15	0.9300	C43—H43	0.9300
C16—C17	1.456 (4)	C44—C45	1.344 (5)
C17—C18	1.397 (4)	C44—H44	0.9300
C17—C22	1.411 (4)	C45—C46	1.384 (5)
C18—C19	1.370 (4)	C45—H45	0.9300
C18—H18	0.9300	C46—C47	1.372 (5)
C19—C20	1.376 (5)	C46—H46	0.9300
C19—H19	0.9300	C47—H47	0.9300

C11—Ir1—C22	91.12 (11)	C19—C20—C21	120.7 (3)
C11—Ir1—N1	80.35 (10)	C19—C20—H20	119.7
C22—Ir1—N1	92.62 (10)	C21—C20—H20	119.7
C11—Ir1—N2	94.40 (10)	C20—C21—C22	121.5 (3)
C22—Ir1—N2	80.07 (10)	C20—C21—H21	119.2
N1—Ir1—N2	170.97 (9)	C22—C21—H21	119.2
C11—Ir1—P1	93.75 (8)	C21—C22—C17	116.6 (3)
C22—Ir1—P1	174.57 (8)	C21—C22—Ir1	129.1 (2)
N1—Ir1—P1	85.83 (6)	C17—C22—Ir1	114.18 (19)
N2—Ir1—P1	101.93 (6)	C24—C23—C28	117.8 (3)
C11—Ir1—Cl1	175.37 (8)	C24—C23—P1	118.9 (2)
C22—Ir1—Cl1	87.54 (8)	C28—C23—P1	122.8 (3)
N1—Ir1—Cl1	95.27 (7)	C25—C24—C23	121.5 (3)
N2—Ir1—Cl1	89.74 (7)	C25—C24—H24	119.3
P1—Ir1—Cl1	87.41 (3)	C23—C24—H24	119.3
C23—P1—C35	105.78 (14)	C26—C25—C24	120.1 (4)
C23—P1—C29	104.84 (14)	C26—C25—H25	119.9
C35—P1—C29	100.97 (13)	C24—C25—H25	119.9
C23—P1—Ir1	111.90 (9)	C27—C26—C25	119.3 (4)
C35—P1—Ir1	108.25 (9)	C27—C26—H26	120.3
C29—P1—Ir1	123.42 (10)	C25—C26—H26	120.3
C36—P2—C42	99.77 (13)	C26—C27—C28	121.1 (4)
C36—P2—C35	105.37 (14)	C26—C27—H27	119.4
C42—P2—C35	97.50 (13)	C28—C27—H27	119.4
C1—N1—C5	119.5 (2)	C27—C28—C23	120.2 (3)
C1—N1—Ir1	125.2 (2)	C27—C28—H28	119.9
C5—N1—Ir1	115.23 (18)	C23—C28—H28	119.9
C12—N2—C16	119.0 (2)	C30—C29—C34	119.2 (3)
C12—N2—Ir1	126.07 (19)	C30—C29—P1	118.7 (2)
C16—N2—Ir1	114.83 (18)	C34—C29—P1	121.9 (3)
N1—C1—C2	121.7 (3)	C29—C30—C31	120.6 (4)
N1—C1—H1	119.1	C29—C30—H30	119.7
C2—C1—H1	119.1	C31—C30—H30	119.7
C3—C2—C1	119.5 (3)	C32—C31—C30	119.7 (4)
C3—C2—H2	120.3	C32—C31—H31	120.2
C1—C2—H2	120.3	C30—C31—H31	120.2
C2—C3—C4	119.2 (3)	C33—C32—C31	120.3 (4)
C2—C3—H3	120.4	C33—C32—H32	119.8
C4—C3—H3	120.4	C31—C32—H32	119.8
C3—C4—C5	120.7 (3)	C32—C33—C34	120.1 (4)
C3—C4—H4	119.6	C32—C33—H33	119.9
C5—C4—H4	119.6	C34—C33—H33	119.9
N1—C5—C4	119.1 (3)	C33—C34—C29	120.1 (4)
N1—C5—C6	114.3 (2)	C33—C34—H34	120.0
C4—C5—C6	126.5 (3)	C29—C34—H34	120.0
C7—C6—C11	121.1 (3)	P1—C35—P2	119.78 (16)
C7—C6—C5	123.8 (3)	P1—C35—H35A	107.4
C11—C6—C5	115.1 (3)	P2—C35—H35A	107.4
C8—C7—C6	120.4 (3)	P1—C35—H35B	107.4
C8—C7—H7	119.8	P2—C35—H35B	107.4
C6—C7—H7	119.8	H35A—C35—H35B	106.9
C7—C8—C9	119.2 (3)	C37—C36—C41	117.8 (3)
C7—C8—H8	120.4	C37—C36—P2	126.5 (3)
C9—C8—H8	120.4	C41—C36—P2	115.4 (2)
C8—C9—C10	121.0 (3)	C36—C37—C38	121.6 (4)
C8—C9—H9	119.5	C36—C37—H37	119.2
C10—C9—H9	119.5	C38—C37—H37	119.2
C9—C10—C11	121.7 (3)	C39—C38—C37	119.4 (4)
C9—C10—H10	119.1	C39—C38—H38	120.3
C11—C10—H10	119.1	C37—C38—H38	120.3
C10—C11—C6	116.5 (3)	C40—C39—C38	120.0 (4)
C10—C11—Ir1	129.5 (2)	C40—C39—H39	120.0
C6—C11—Ir1	114.0 (2)	C38—C39—H39	120.0
N2—C12—C13	122.8 (3)	C39—C40—C41	120.3 (4)
N2—C12—H12	118.6	C39—C40—H40	119.9
C13—C12—H12	118.6	C41—C40—H40	119.9
C14—C13—C12	118.8 (3)	C36—C41—C40	120.9 (4)
C14—C13—H13	120.6	C36—C41—H41	119.6
C12—C13—H13	120.6	C40—C41—H41	119.6
C13—C14—C15	119.2 (3)	C43—C42—C47	117.5 (3)
C13—C14—H14	120.4	C43—C42—P2	123.0 (2)
C15—C14—H14	120.4	C47—C42—P2	119.4 (2)
C14—C15—C16	120.8 (3)	C44—C43—C42	120.4 (3)
C14—C15—H15	119.6	C44—C43—H43	119.8
C16—C15—H15	119.6	C42—C43—H43	119.8
N2—C16—C15	119.3 (3)	C45—C44—C43	121.3 (4)
N2—C16—C17	115.5 (2)	C45—C44—H44	119.3
C15—C16—C17	125.2 (3)	C43—C44—H44	119.3
C18—C17—C22	121.3 (3)	C44—C45—C46	119.7 (3)
C18—C17—C16	123.9 (3)	C44—C45—H45	120.2
C22—C17—C16	114.7 (2)	C46—C45—H45	120.2
C19—C18—C17	119.9 (3)	C47—C46—C45	119.7 (3)
C19—C18—H18	120.0	C47—C46—H46	120.2
C17—C18—H18	120.0	C45—C46—H46	120.2
C18—C19—C20	119.9 (3)	C46—C47—C42	121.3 (3)
C18—C19—H19	120.1	C46—C47—H47	119.3
C20—C19—H19	120.1	C42—C47—H47	119.3

C5—N1—C1—C2	−3.1 (4)	C35—P1—C23—C28	−21.3 (3)
Ir1—N1—C1—C2	175.3 (2)	C29—P1—C23—C28	−127.5 (2)
N1—C1—C2—C3	−1.0 (5)	Ir1—P1—C23—C28	96.4 (2)
C1—C2—C3—C4	2.3 (5)	C28—C23—C24—C25	−0.2 (5)
C2—C3—C4—C5	0.3 (5)	P1—C23—C24—C25	171.8 (3)
C1—N1—C5—C4	5.6 (4)	C23—C24—C25—C26	−0.4 (6)
Ir1—N1—C5—C4	−172.9 (2)	C24—C25—C26—C27	0.8 (6)
C1—N1—C5—C6	−173.3 (3)	C25—C26—C27—C28	−0.6 (6)
Ir1—N1—C5—C6	8.1 (3)	C26—C27—C28—C23	0.0 (5)
C3—C4—C5—N1	−4.3 (4)	C24—C23—C28—C27	0.4 (5)
C3—C4—C5—C6	174.5 (3)	P1—C23—C28—C27	−171.3 (2)
N1—C5—C6—C7	176.2 (3)	C23—P1—C29—C30	−168.8 (3)
C4—C5—C6—C7	−2.6 (5)	C35—P1—C29—C30	81.4 (3)
N1—C5—C6—C11	−1.6 (4)	Ir1—P1—C29—C30	−39.2 (3)
C4—C5—C6—C11	179.6 (3)	C23—P1—C29—C34	17.0 (3)
C11—C6—C7—C8	1.2 (5)	C35—P1—C29—C34	−92.8 (3)
C5—C6—C7—C8	−176.5 (3)	Ir1—P1—C29—C34	146.5 (2)
C6—C7—C8—C9	1.5 (5)	C34—C29—C30—C31	1.5 (5)
C7—C8—C9—C10	−2.3 (5)	P1—C29—C30—C31	−172.9 (3)
C8—C9—C10—C11	0.3 (5)	C29—C30—C31—C32	−1.2 (6)
C9—C10—C11—C6	2.3 (4)	C30—C31—C32—C33	0.2 (7)
C9—C10—C11—Ir1	−177.0 (2)	C31—C32—C33—C34	0.5 (7)
C7—C6—C11—C10	−3.1 (4)	C32—C33—C34—C29	−0.2 (6)
C5—C6—C11—C10	174.9 (3)	C30—C29—C34—C33	−0.8 (5)
C7—C6—C11—Ir1	176.3 (2)	P1—C29—C34—C33	173.4 (3)
C5—C6—C11—Ir1	−5.8 (3)	C23—P1—C35—P2	−56.6 (2)
C16—N2—C12—C13	−2.7 (5)	C29—P1—C35—P2	52.4 (2)
Ir1—N2—C12—C13	−179.5 (3)	Ir1—P1—C35—P2	−176.66 (14)
N2—C12—C13—C14	0.4 (6)	C36—P2—C35—P1	−93.0 (2)
C12—C13—C14—C15	0.6 (6)	C42—P2—C35—P1	164.65 (18)
C13—C14—C15—C16	0.6 (6)	C42—P2—C36—C37	76.6 (3)
C12—N2—C16—C15	3.9 (4)	C35—P2—C36—C37	−24.0 (3)
Ir1—N2—C16—C15	−179.0 (2)	C42—P2—C36—C41	−97.0 (3)
C12—N2—C16—C17	−174.2 (3)	C35—P2—C36—C41	162.4 (2)
Ir1—N2—C16—C17	3.0 (3)	C41—C36—C37—C38	−0.6 (5)
C14—C15—C16—N2	−2.9 (5)	P2—C36—C37—C38	−174.1 (3)
C14—C15—C16—C17	174.9 (3)	C36—C37—C38—C39	1.0 (7)
N2—C16—C17—C18	−178.7 (3)	C37—C38—C39—C40	0.5 (7)
C15—C16—C17—C18	3.4 (5)	C38—C39—C40—C41	−2.4 (6)
N2—C16—C17—C22	3.7 (4)	C37—C36—C41—C40	−1.3 (5)
C15—C16—C17—C22	−174.2 (3)	P2—C36—C41—C40	172.9 (3)
C22—C17—C18—C19	2.3 (5)	C39—C40—C41—C36	2.8 (6)
C16—C17—C18—C19	−175.2 (3)	C36—P2—C42—C43	16.7 (3)
C17—C18—C19—C20	−0.4 (5)	C35—P2—C42—C43	123.8 (3)
C18—C19—C20—C21	−0.9 (5)	C36—P2—C42—C47	−166.7 (2)
C19—C20—C21—C22	0.4 (5)	C35—P2—C42—C47	−59.6 (3)
C20—C21—C22—C17	1.4 (4)	C47—C42—C43—C44	0.6 (5)
C20—C21—C22—Ir1	−174.3 (2)	P2—C42—C43—C44	177.3 (3)
C18—C17—C22—C21	−2.7 (4)	C42—C43—C44—C45	−0.6 (6)
C16—C17—C22—C21	175.0 (3)	C43—C44—C45—C46	1.0 (7)
C18—C17—C22—Ir1	173.6 (2)	C44—C45—C46—C47	−1.5 (6)
C16—C17—C22—Ir1	−8.7 (3)	C45—C46—C47—C42	1.5 (5)
C35—P1—C23—C24	167.1 (2)	C43—C42—C47—C46	−1.1 (5)
C29—P1—C23—C24	60.9 (3)	P2—C42—C47—C46	−177.9 (3)
Ir1—P1—C23—C24	−75.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg6, Cg8 and Cg10 are the centroids of the C17–C22, C29–C34 and C42–C47 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1	0.93	2.73	3.357 (3)	126
C14—H14···Cl1ⁱ	0.93	2.77	3.548 (4)	142
C30—H30···Cl1	0.93	2.84	3.664 (4)	148
C35—H35A···Cl1	0.97	2.83	3.460 (3)	124
C3—H3···Cg6ⁱⁱ	0.93	2.83	3.572 (4)	137
C26—H26···Cg10ⁱⁱⁱ	0.93	2.79	3.575 (5)	143
C38—H38···C10ⁱⁱⁱ	0.93	2.81	3.659 (5)	153
C40—H40···Cg8^iv	0.93	2.95	3.711 (5)	140

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+3/2, y+1/2, −z+3/2; (iii) −x+2, −y+1, −z+2; (iv) −x+3/2, y+1/2, −z+5/2.

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Synthesis, crystal structure and Hirshfeld surface analysis of [bis­(di­phenyl­phosphan­yl)methane-κP]chloridobis­[2-(pyridin-2-yl)phenyl-κ2N,C1]iridium(III)

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Synthesis, crystal structure and Hirshfeld surface analysis of [bis(diphenylphosphanyl)methane-κP]chloridobis[2-(pyridin-2-yl)phenyl-κ²N,C¹]iridium(III)