Inter­molecular hydrogen bonding in isostructural pincer complexes [OH-(^t-BuPOCOP^t-Bu)MCl] (M = Pd and Pt)

In the crystal structure of the isostructural title compounds [OH-(^t-BuPOCOP^t-Bu)PdCl] and [OH-(^t-BuPOCOP^t-Bu)PtCl] the M^II centres are coordinated in a distorted square-planar fashion by the pincer and the chloride ligand.

Key indicators

Structure: 1

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.018
• wR factor = 0.046
• Data-to-parameter ratio = 23.1

Structure: 2

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.016
• wR factor = 0.037
• Data-to-parameter ratio = 23.1

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .         70 Ang   3

Alert level G
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Pd1      --Cl1      .        7.0 s.u.
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O1             114.4 Degree
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O3             114.3 Degree
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          2 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 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

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




Datablock: 2


Alert level C
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .         69 Ang   3
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O1             115.0 Degree
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O3             114.9 Degree
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 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
   2 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

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

---

Computing details

For both structures, 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: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

{2,6-Bis[(di-tert-butylphosphanyl)oxy]-4-hydroxyphenyl}chloridopalladium(II) (1)

Crystal data

[Pd(C22H39O3P2)Cl]	F(000) = 1152
Mr = 555.32	Dx = 1.389 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.7678 (5) Å	Cell parameters from 9082 reflections
b = 20.1652 (10) Å	θ = 2.4–30.5°
c = 13.9656 (7) Å	µ = 0.94 mm^−1
β = 105.1743 (8)°	T = 150 K
V = 2654.9 (2) Å^3	Prism, colourless
Z = 4	0.37 × 0.36 × 0.36 mm

Data collection

Bruker APEXII CCD diffractometer	6411 independent reflections
Radiation source: fine-focus sealed tube	6166 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm^-1	Rint = 0.018
φ and ω scans	θmax = 28.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −12→12
Tmin = 0.68, Tmax = 0.73	k = −26→26
57317 measured reflections	l = −18→18

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.018	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.046	w = 1/[σ^2(Fo^2) + (0.0197P)^2 + 1.5724P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
6411 reflections	Δρmax = 0.49 e Å^−3
278 parameters	Δρmin = −0.45 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.

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

	x	y	z	Uiso*/Ueq
C1	0.21967 (12)	0.29775 (6)	−0.06646 (9)	0.0158 (2)
C2	0.32101 (13)	0.27370 (6)	−0.11161 (9)	0.0157 (2)
C3	0.38045 (13)	0.31168 (6)	−0.17336 (9)	0.0168 (2)
H3	0.4473	0.2932	−0.2044	0.020*
C4	0.33893 (13)	0.37773 (6)	−0.18831 (9)	0.0174 (2)
C5	0.23941 (13)	0.40494 (6)	−0.14407 (9)	0.0187 (2)
H5	0.2125	0.4502	−0.1537	0.022*
C6	0.18083 (12)	0.36393 (6)	−0.08548 (9)	0.0165 (2)
C7	0.20805 (14)	0.09712 (7)	−0.10482 (10)	0.0232 (3)
C8	0.11293 (18)	0.13104 (9)	−0.19722 (12)	0.0396 (4)
H8A	0.1715	0.1584	−0.2289	0.059*
H8B	0.0431	0.1591	−0.1775	0.059*
H8C	0.0636	0.0972	−0.2440	0.059*
C9	0.11526 (19)	0.05436 (9)	−0.05637 (14)	0.0406 (4)
H9A	0.0636	0.0218	−0.1044	0.061*
H9B	0.0474	0.0827	−0.0348	0.061*
H9C	0.1754	0.0313	0.0012	0.061*
C10	0.31748 (17)	0.05426 (7)	−0.13615 (13)	0.0325 (3)
H10A	0.3734	0.0297	−0.0786	0.049*
H10B	0.3805	0.0826	−0.1625	0.049*
H10C	0.2689	0.0229	−0.1875	0.049*
C11	0.44379 (14)	0.14362 (7)	0.08081 (10)	0.0227 (3)
C12	0.40374 (18)	0.08715 (8)	0.14186 (12)	0.0351 (3)
H12A	0.4794	0.0811	0.2030	0.053*
H12B	0.3911	0.0461	0.1030	0.053*
H12C	0.3151	0.0982	0.1586	0.053*
C13	0.57549 (15)	0.12576 (8)	0.04517 (12)	0.0315 (3)
H13A	0.6557	0.1171	0.1027	0.047*
H13B	0.5989	0.1628	0.0068	0.047*
H13C	0.5557	0.0861	0.0033	0.047*
C14	0.47797 (16)	0.20604 (8)	0.14625 (11)	0.0300 (3)
H14A	0.3977	0.2163	0.1736	0.045*
H14B	0.4951	0.2435	0.1061	0.045*
H14C	0.5629	0.1980	0.2006	0.045*
C15	−0.16995 (14)	0.34028 (7)	−0.02248 (11)	0.0246 (3)
C16	−0.22961 (16)	0.40832 (8)	−0.06139 (13)	0.0354 (3)
H16A	−0.3313	0.4043	−0.0934	0.053*
H16B	−0.1806	0.4245	−0.1097	0.053*
H16C	−0.2150	0.4396	−0.0060	0.053*
C17	−0.24584 (17)	0.31354 (9)	0.05250 (14)	0.0405 (4)
H17A	−0.3467	0.3073	0.0197	0.061*
H17B	−0.2356	0.3453	0.1071	0.061*
H17C	−0.2038	0.2710	0.0787	0.061*
C18	−0.19456 (18)	0.29240 (10)	−0.11087 (14)	0.0428 (4)
H18A	−0.1665	0.2475	−0.0867	0.064*
H18B	−0.1376	0.3065	−0.1555	0.064*
H18C	−0.2952	0.2926	−0.1468	0.064*
C19	0.08541 (15)	0.38393 (7)	0.15092 (10)	0.0228 (3)
C20	0.24411 (17)	0.39741 (9)	0.16379 (13)	0.0383 (4)
H20A	0.2846	0.4180	0.2286	0.057*
H20B	0.2558	0.4273	0.1112	0.057*
H20C	0.2931	0.3555	0.1598	0.057*
C21	0.00919 (17)	0.44979 (7)	0.15343 (11)	0.0291 (3)
H21A	−0.0898	0.4413	0.1529	0.044*
H21B	0.0122	0.4762	0.0952	0.044*
H21C	0.0562	0.4741	0.2138	0.044*
C22	0.0681 (2)	0.33840 (8)	0.23496 (11)	0.0363 (4)
H22A	0.1114	0.3593	0.2991	0.054*
H22B	0.1148	0.2959	0.2309	0.054*
H22C	−0.0330	0.3309	0.2286	0.054*
Cl1	0.03724 (5)	0.17138 (2)	0.12263 (3)	0.03930 (10)
O1	0.36634 (9)	0.20853 (4)	−0.09447 (7)	0.01852 (17)
O2	0.39346 (11)	0.41889 (5)	−0.24683 (8)	0.0243 (2)
O3	0.07741 (9)	0.39017 (4)	−0.04466 (7)	0.01986 (18)
P1	0.28824 (3)	0.16660 (2)	−0.02188 (2)	0.01575 (6)
P2	0.02457 (3)	0.33937 (2)	0.03141 (2)	0.01631 (6)
Pd1	0.13707 (2)	0.24105 (2)	0.02025 (2)	0.01624 (3)
H2	0.435 (2)	0.3971 (10)	−0.2769 (15)	0.039 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0166 (5)	0.0163 (5)	0.0162 (5)	0.0017 (4)	0.0072 (4)	0.0020 (4)
C2	0.0173 (5)	0.0139 (5)	0.0161 (5)	0.0029 (4)	0.0049 (4)	0.0016 (4)
C3	0.0168 (5)	0.0179 (5)	0.0179 (5)	0.0027 (4)	0.0082 (4)	0.0014 (4)
C4	0.0193 (5)	0.0170 (5)	0.0179 (5)	0.0004 (4)	0.0082 (4)	0.0031 (4)
C5	0.0218 (6)	0.0143 (5)	0.0220 (6)	0.0030 (4)	0.0094 (5)	0.0028 (4)
C6	0.0160 (5)	0.0177 (5)	0.0175 (5)	0.0028 (4)	0.0072 (4)	−0.0006 (4)
C7	0.0253 (6)	0.0210 (6)	0.0261 (6)	−0.0039 (5)	0.0113 (5)	−0.0061 (5)
C8	0.0368 (8)	0.0459 (9)	0.0296 (8)	0.0011 (7)	−0.0031 (6)	−0.0098 (7)
C9	0.0457 (9)	0.0371 (9)	0.0478 (10)	−0.0214 (7)	0.0282 (8)	−0.0155 (7)
C10	0.0361 (8)	0.0236 (7)	0.0432 (9)	−0.0029 (6)	0.0199 (7)	−0.0129 (6)
C11	0.0245 (6)	0.0212 (6)	0.0213 (6)	0.0024 (5)	0.0041 (5)	0.0058 (5)
C12	0.0422 (9)	0.0301 (8)	0.0312 (8)	0.0009 (6)	0.0065 (7)	0.0154 (6)
C13	0.0246 (7)	0.0330 (8)	0.0351 (8)	0.0087 (6)	0.0047 (6)	0.0049 (6)
C14	0.0317 (7)	0.0327 (7)	0.0228 (7)	−0.0025 (6)	0.0022 (6)	−0.0009 (6)
C15	0.0180 (6)	0.0280 (7)	0.0287 (7)	−0.0009 (5)	0.0078 (5)	−0.0009 (5)
C16	0.0223 (7)	0.0364 (8)	0.0455 (9)	0.0061 (6)	0.0051 (6)	0.0065 (7)
C17	0.0279 (8)	0.0462 (9)	0.0537 (10)	−0.0051 (7)	0.0218 (7)	0.0081 (8)
C18	0.0291 (8)	0.0500 (10)	0.0424 (9)	0.0002 (7)	−0.0030 (7)	−0.0173 (8)
C19	0.0275 (6)	0.0208 (6)	0.0204 (6)	0.0026 (5)	0.0069 (5)	−0.0027 (5)
C20	0.0272 (7)	0.0430 (9)	0.0407 (9)	−0.0008 (7)	0.0015 (6)	−0.0151 (7)
C21	0.0411 (8)	0.0198 (6)	0.0289 (7)	0.0050 (6)	0.0133 (6)	−0.0036 (5)
C22	0.0612 (11)	0.0277 (7)	0.0209 (7)	0.0105 (7)	0.0125 (7)	0.0021 (6)
Cl1	0.0649 (3)	0.02367 (16)	0.0452 (2)	−0.00300 (16)	0.0427 (2)	0.00352 (15)
O1	0.0233 (4)	0.0142 (4)	0.0219 (4)	0.0054 (3)	0.0127 (4)	0.0047 (3)
O2	0.0318 (5)	0.0179 (4)	0.0308 (5)	0.0036 (4)	0.0215 (4)	0.0065 (4)
O3	0.0224 (4)	0.0166 (4)	0.0256 (4)	0.0048 (3)	0.0152 (4)	0.0032 (3)
P1	0.01950 (14)	0.01287 (13)	0.01668 (14)	0.00141 (11)	0.00791 (11)	0.00152 (10)
P2	0.01767 (14)	0.01587 (14)	0.01803 (14)	0.00131 (11)	0.00938 (11)	−0.00007 (11)
Pd1	0.02072 (5)	0.01407 (5)	0.01727 (5)	0.00096 (3)	0.01092 (4)	0.00110 (3)

Geometric parameters (Å, º)

C1—C2	1.3926 (16)	C14—H14A	0.9800
C1—C6	1.3937 (16)	C14—H14B	0.9800
C1—Pd1	1.9841 (12)	C14—H14C	0.9800
C2—O1	1.3873 (14)	C15—C17	1.531 (2)
C2—C3	1.3891 (16)	C15—C16	1.533 (2)
C3—C4	1.3920 (17)	C15—C18	1.536 (2)
C3—H3	0.9500	C15—P2	1.8516 (14)
C4—O2	1.3670 (14)	C16—H16A	0.9800
C4—C5	1.3936 (17)	C16—H16B	0.9800
C5—C6	1.3878 (17)	C16—H16C	0.9800
C5—H5	0.9500	C17—H17A	0.9800
C6—O3	1.3881 (14)	C17—H17B	0.9800
C7—C10	1.5250 (19)	C17—H17C	0.9800
C7—C9	1.531 (2)	C18—H18A	0.9800
C7—C8	1.539 (2)	C18—H18B	0.9800
C7—P1	1.8557 (13)	C18—H18C	0.9800
C8—H8A	0.9800	C19—C21	1.5274 (18)
C8—H8B	0.9800	C19—C22	1.534 (2)
C8—H8C	0.9800	C19—C20	1.537 (2)
C9—H9A	0.9800	C19—P2	1.8512 (13)
C9—H9B	0.9800	C20—H20A	0.9800
C9—H9C	0.9800	C20—H20B	0.9800
C10—H10A	0.9800	C20—H20C	0.9800
C10—H10B	0.9800	C21—H21A	0.9800
C10—H10C	0.9800	C21—H21B	0.9800
C11—C12	1.5334 (19)	C21—H21C	0.9800
C11—C13	1.539 (2)	C22—H22A	0.9800
C11—C14	1.540 (2)	C22—H22B	0.9800
C11—P1	1.8545 (13)	C22—H22C	0.9800
C12—H12A	0.9800	Cl1—Pd1	2.3871 (4)
C12—H12B	0.9800	O1—P1	1.6521 (9)
C12—H12C	0.9800	O2—H2	0.79 (2)
C13—H13A	0.9800	O3—P2	1.6527 (9)
C13—H13B	0.9800	P1—Pd1	2.2880 (3)
C13—H13C	0.9800	P2—Pd1	2.2918 (3)
C2—C1—C6	115.95 (11)	C16—C15—C18	108.22 (13)
C2—C1—Pd1	121.76 (9)	C17—C15—P2	110.34 (11)
C6—C1—Pd1	122.29 (9)	C16—C15—P2	114.03 (10)
O1—C2—C3	117.58 (10)	C18—C15—P2	104.39 (10)
O1—C2—C1	118.97 (10)	C15—C16—H16A	109.5
C3—C2—C1	123.44 (11)	C15—C16—H16B	109.5
C2—C3—C4	117.90 (11)	H16A—C16—H16B	109.5
C2—C3—H3	121.0	C15—C16—H16C	109.5
C4—C3—H3	121.0	H16A—C16—H16C	109.5
O2—C4—C3	121.80 (11)	H16B—C16—H16C	109.5
O2—C4—C5	116.88 (11)	C15—C17—H17A	109.5
C3—C4—C5	121.33 (11)	C15—C17—H17B	109.5
C6—C5—C4	118.03 (11)	H17A—C17—H17B	109.5
C6—C5—H5	121.0	C15—C17—H17C	109.5
C4—C5—H5	121.0	H17A—C17—H17C	109.5
C5—C6—O3	118.14 (11)	H17B—C17—H17C	109.5
C5—C6—C1	123.31 (11)	C15—C18—H18A	109.5
O3—C6—C1	118.54 (10)	C15—C18—H18B	109.5
C10—C7—C9	110.38 (12)	H18A—C18—H18B	109.5
C10—C7—C8	109.03 (13)	C15—C18—H18C	109.5
C9—C7—C8	108.88 (13)	H18A—C18—H18C	109.5
C10—C7—P1	113.20 (10)	H18B—C18—H18C	109.5
C9—C7—P1	110.57 (10)	C21—C19—C22	110.54 (12)
C8—C7—P1	104.56 (10)	C21—C19—C20	109.04 (12)
C7—C8—H8A	109.5	C22—C19—C20	109.04 (13)
C7—C8—H8B	109.5	C21—C19—P2	113.53 (10)
H8A—C8—H8B	109.5	C22—C19—P2	109.00 (10)
C7—C8—H8C	109.5	C20—C19—P2	105.49 (9)
H8A—C8—H8C	109.5	C19—C20—H20A	109.5
H8B—C8—H8C	109.5	C19—C20—H20B	109.5
C7—C9—H9A	109.5	H20A—C20—H20B	109.5
C7—C9—H9B	109.5	C19—C20—H20C	109.5
H9A—C9—H9B	109.5	H20A—C20—H20C	109.5
C7—C9—H9C	109.5	H20B—C20—H20C	109.5
H9A—C9—H9C	109.5	C19—C21—H21A	109.5
H9B—C9—H9C	109.5	C19—C21—H21B	109.5
C7—C10—H10A	109.5	H21A—C21—H21B	109.5
C7—C10—H10B	109.5	C19—C21—H21C	109.5
H10A—C10—H10B	109.5	H21A—C21—H21C	109.5
C7—C10—H10C	109.5	H21B—C21—H21C	109.5
H10A—C10—H10C	109.5	C19—C22—H22A	109.5
H10B—C10—H10C	109.5	C19—C22—H22B	109.5
C12—C11—C13	111.26 (12)	H22A—C22—H22B	109.5
C12—C11—C14	108.92 (12)	C19—C22—H22C	109.5
C13—C11—C14	108.27 (12)	H22A—C22—H22C	109.5
C12—C11—P1	109.81 (10)	H22B—C22—H22C	109.5
C13—C11—P1	113.17 (10)	C2—O1—P1	114.38 (7)
C14—C11—P1	105.13 (9)	C4—O2—H2	108.4 (15)
C11—C12—H12A	109.5	C6—O3—P2	114.27 (8)
C11—C12—H12B	109.5	O1—P1—C11	100.72 (5)
H12A—C12—H12B	109.5	O1—P1—C7	100.99 (5)
C11—C12—H12C	109.5	C11—P1—C7	114.87 (6)
H12A—C12—H12C	109.5	O1—P1—Pd1	104.76 (3)
H12B—C12—H12C	109.5	C11—P1—Pd1	114.73 (5)
C11—C13—H13A	109.5	C7—P1—Pd1	117.42 (4)
C11—C13—H13B	109.5	O3—P2—C19	101.43 (6)
H13A—C13—H13B	109.5	O3—P2—C15	101.10 (6)
C11—C13—H13C	109.5	C19—P2—C15	114.50 (6)
H13A—C13—H13C	109.5	O3—P2—Pd1	104.87 (3)
H13B—C13—H13C	109.5	C19—P2—Pd1	115.77 (4)
C11—C14—H14A	109.5	C15—P2—Pd1	116.12 (5)
C11—C14—H14B	109.5	C1—Pd1—P1	80.11 (3)
H14A—C14—H14B	109.5	C1—Pd1—P2	79.73 (3)
C11—C14—H14C	109.5	P1—Pd1—P2	159.768 (12)
H14A—C14—H14C	109.5	C1—Pd1—Cl1	179.06 (4)
H14B—C14—H14C	109.5	P1—Pd1—Cl1	99.219 (13)
C17—C15—C16	110.51 (13)	P2—Pd1—Cl1	100.957 (13)
C17—C15—C18	109.05 (14)
C6—C1—C2—O1	178.90 (10)	C14—C11—P1—Pd1	−31.95 (10)
Pd1—C1—C2—O1	−0.73 (16)	C10—C7—P1—O1	61.39 (11)
C6—C1—C2—C3	−0.88 (18)	C9—C7—P1—O1	−174.18 (11)
Pd1—C1—C2—C3	179.49 (9)	C8—C7—P1—O1	−57.15 (10)
O1—C2—C3—C4	−177.93 (11)	C10—C7—P1—C11	−46.00 (13)
C1—C2—C3—C4	1.85 (19)	C9—C7—P1—C11	78.44 (12)
C2—C3—C4—O2	179.12 (11)	C8—C7—P1—C11	−164.53 (10)
C2—C3—C4—C5	−0.89 (19)	C10—C7—P1—Pd1	174.54 (9)
O2—C4—C5—C6	179.06 (11)	C9—C7—P1—Pd1	−61.03 (12)
C3—C4—C5—C6	−0.93 (19)	C8—C7—P1—Pd1	56.00 (11)
C4—C5—C6—O3	−177.39 (11)	C6—O3—P2—C19	114.99 (9)
C4—C5—C6—C1	1.99 (19)	C6—O3—P2—C15	−126.92 (9)
C2—C1—C6—C5	−1.10 (18)	C6—O3—P2—Pd1	−5.84 (9)
Pd1—C1—C6—C5	178.53 (10)	C21—C19—P2—O3	65.88 (11)
C2—C1—C6—O3	178.27 (11)	C22—C19—P2—O3	−170.43 (10)
Pd1—C1—C6—O3	−2.10 (16)	C20—C19—P2—O3	−53.46 (11)
C3—C2—O1—P1	−178.98 (9)	C21—C19—P2—C15	−42.05 (12)
C1—C2—O1—P1	1.23 (14)	C22—C19—P2—C15	81.64 (12)
C5—C6—O3—P2	−175.03 (9)	C20—C19—P2—C15	−161.39 (10)
C1—C6—O3—P2	5.56 (14)	C21—C19—P2—Pd1	178.72 (8)
C2—O1—P1—C11	−120.43 (9)	C22—C19—P2—Pd1	−57.59 (11)
C2—O1—P1—C7	121.36 (9)	C20—C19—P2—Pd1	59.38 (11)
C2—O1—P1—Pd1	−1.08 (9)	C17—C15—P2—O3	−162.98 (11)
C12—C11—P1—O1	−163.04 (10)	C16—C15—P2—O3	−37.91 (12)
C13—C11—P1—O1	−38.05 (11)	C18—C15—P2—O3	79.99 (11)
C14—C11—P1—O1	79.93 (10)	C17—C15—P2—C19	−54.84 (13)
C12—C11—P1—C7	−55.49 (12)	C16—C15—P2—C19	70.22 (12)
C13—C11—P1—C7	69.50 (11)	C18—C15—P2—C19	−171.88 (11)
C14—C11—P1—C7	−172.52 (9)	C17—C15—P2—Pd1	84.24 (11)
C12—C11—P1—Pd1	85.08 (10)	C16—C15—P2—Pd1	−150.70 (10)
C13—C11—P1—Pd1	−149.93 (9)	C18—C15—P2—Pd1	−32.80 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···Cl1^i	0.79 (2)	2.37 (2)	3.1545 (11)	174.2 (19)

Symmetry code: (i) x+1/2, −y+1/2, z−1/2.

{2,6-Bis[(di-tert-butylphosphanyl)oxy]-4-hydroxyphenyl}chloridoplatinum(II) (2)

Crystal data

[Pt(C22H39O3P2)Cl]	F(000) = 1280
Mr = 644.01	Dx = 1.611 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.7722 (8) Å	Cell parameters from 9874 reflections
b = 20.1562 (16) Å	θ = 2.3–30.5°
c = 13.9699 (11) Å	µ = 5.52 mm^−1
β = 105.1634 (13)°	T = 150 K
V = 2655.9 (4) Å^3	Prism, colourless
Z = 4	0.34 × 0.21 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer	6413 independent reflections
Radiation source: fine-focus sealed tube	5959 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm^-1	Rint = 0.023
φ and ω scans	θmax = 28.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −8→12
Tmin = 0.34, Tmax = 0.50	k = −25→26
25029 measured reflections	l = −18→18

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.016	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.037	w = 1/[σ^2(Fo^2) + (0.0128P)^2 + 2.002P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
6413 reflections	Δρmax = 0.87 e Å^−3
278 parameters	Δρmin = −0.84 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.

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

	x	y	z	Uiso*/Ueq
C1	0.2222 (2)	0.29907 (9)	−0.06632 (13)	0.0156 (4)
C2	0.3236 (2)	0.27501 (9)	−0.11116 (14)	0.0156 (4)
C3	0.3826 (2)	0.31281 (9)	−0.17280 (14)	0.0162 (4)
H3	0.4495	0.2943	−0.2038	0.019*
C4	0.3405 (2)	0.37898 (9)	−0.18783 (14)	0.0165 (4)
C5	0.2411 (2)	0.40605 (9)	−0.14397 (14)	0.0186 (4)
H5	0.2139	0.4513	−0.1539	0.022*
C6	0.1826 (2)	0.36515 (9)	−0.08529 (14)	0.0160 (4)
C7	0.2082 (2)	0.09861 (10)	−0.10463 (16)	0.0224 (4)
C8	0.1139 (3)	0.13295 (13)	−0.19738 (17)	0.0368 (6)
H8A	0.1731	0.1604	−0.2285	0.055*
H8B	0.0438	0.1610	−0.1780	0.055*
H8C	0.0650	0.0993	−0.2446	0.055*
C9	0.1142 (3)	0.05599 (12)	−0.0570 (2)	0.0389 (6)
H9A	0.0616	0.0240	−0.1057	0.058*
H9B	0.0473	0.0845	−0.0348	0.058*
H9C	0.1736	0.0322	0.0000	0.058*
C10	0.3175 (3)	0.05516 (11)	−0.13603 (18)	0.0315 (5)
H10A	0.3703	0.0290	−0.0791	0.047*
H10B	0.3835	0.0834	−0.1597	0.047*
H10C	0.2689	0.0252	−0.1894	0.047*
C11	0.4449 (2)	0.14387 (10)	0.08141 (15)	0.0219 (4)
C12	0.4032 (3)	0.08751 (11)	0.14229 (18)	0.0338 (5)
H12A	0.4785	0.0811	0.2035	0.051*
H12B	0.3897	0.0465	0.1033	0.051*
H12C	0.3147	0.0991	0.1589	0.051*
C13	0.5752 (2)	0.12509 (11)	0.04526 (18)	0.0313 (5)
H13A	0.6550	0.1151	0.1025	0.047*
H13B	0.6005	0.1622	0.0079	0.047*
H13C	0.5534	0.0860	0.0023	0.047*
C14	0.4811 (3)	0.20604 (11)	0.14718 (16)	0.0282 (5)
H14A	0.4008	0.2172	0.1740	0.042*
H14B	0.5004	0.2432	0.1075	0.042*
H14C	0.5650	0.1973	0.2019	0.042*
C15	−0.1691 (2)	0.34070 (11)	−0.02288 (16)	0.0233 (4)
C16	−0.2283 (3)	0.40901 (12)	−0.06013 (19)	0.0345 (5)
H16A	−0.3300	0.4053	−0.0919	0.052*
H16B	−0.1795	0.4257	−0.1083	0.052*
H16C	−0.2133	0.4398	−0.0040	0.052*
C17	−0.2449 (3)	0.31316 (13)	0.0515 (2)	0.0392 (6)
H17A	−0.3454	0.3062	0.0183	0.059*
H17B	−0.2362	0.3448	0.1061	0.059*
H17C	−0.2018	0.2708	0.0778	0.059*
C18	−0.1939 (3)	0.29371 (14)	−0.1125 (2)	0.0413 (6)
H18A	−0.1673	0.2484	−0.0894	0.062*
H18B	−0.1360	0.3080	−0.1563	0.062*
H18C	−0.2943	0.2947	−0.1489	0.062*
C19	0.0864 (2)	0.38351 (10)	0.15143 (15)	0.0221 (4)
C20	0.2450 (3)	0.39706 (13)	0.16472 (19)	0.0371 (6)
H20A	0.2850	0.4177	0.2295	0.056*
H20B	0.2570	0.4270	0.1122	0.056*
H20C	0.2941	0.3551	0.1609	0.056*
C21	0.0100 (3)	0.44929 (10)	0.15415 (16)	0.0277 (5)
H21A	−0.0888	0.4407	0.1539	0.042*
H21B	0.0125	0.4758	0.0958	0.042*
H21C	0.0572	0.4736	0.2145	0.042*
C22	0.0683 (3)	0.33748 (11)	0.23488 (16)	0.0349 (6)
H22A	0.1101	0.3584	0.2992	0.052*
H22B	0.1162	0.2952	0.2311	0.052*
H22C	−0.0328	0.3295	0.2276	0.052*
Cl1	0.03655 (8)	0.17228 (3)	0.12079 (5)	0.03816 (15)
O1	0.36834 (15)	0.20966 (6)	−0.09302 (10)	0.0177 (3)
O2	0.39515 (17)	0.42028 (7)	−0.24662 (11)	0.0241 (3)
O3	0.07860 (15)	0.39053 (6)	−0.04407 (10)	0.0189 (3)
P1	0.28950 (5)	0.16756 (2)	−0.02112 (4)	0.01541 (10)
P2	0.02527 (5)	0.33940 (2)	0.03123 (4)	0.01579 (10)
Pt1	0.13889 (2)	0.24213 (2)	0.01970 (2)	0.01543 (3)
H2	0.441 (3)	0.3988 (14)	−0.277 (2)	0.039 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0183 (10)	0.0158 (8)	0.0138 (9)	0.0009 (7)	0.0064 (7)	0.0017 (6)
C2	0.0180 (10)	0.0129 (8)	0.0154 (9)	0.0025 (7)	0.0035 (7)	0.0013 (7)
C3	0.0164 (9)	0.0175 (8)	0.0170 (9)	0.0027 (7)	0.0085 (7)	0.0014 (7)
C4	0.0169 (10)	0.0180 (8)	0.0158 (9)	−0.0004 (7)	0.0067 (7)	0.0040 (7)
C5	0.0225 (10)	0.0144 (8)	0.0206 (10)	0.0029 (7)	0.0085 (8)	0.0031 (7)
C6	0.0155 (9)	0.0173 (8)	0.0167 (9)	0.0032 (7)	0.0071 (7)	−0.0005 (7)
C7	0.0268 (11)	0.0183 (9)	0.0243 (11)	−0.0033 (8)	0.0106 (9)	−0.0060 (7)
C8	0.0354 (14)	0.0417 (13)	0.0280 (13)	0.0003 (11)	−0.0015 (10)	−0.0112 (10)
C9	0.0459 (16)	0.0342 (12)	0.0454 (15)	−0.0206 (11)	0.0273 (13)	−0.0161 (11)
C10	0.0357 (14)	0.0232 (10)	0.0411 (14)	−0.0033 (9)	0.0198 (11)	−0.0124 (9)
C11	0.0255 (11)	0.0191 (9)	0.0199 (10)	0.0026 (8)	0.0037 (8)	0.0056 (7)
C12	0.0404 (14)	0.0291 (11)	0.0297 (13)	0.0012 (10)	0.0049 (11)	0.0158 (9)
C13	0.0257 (12)	0.0321 (11)	0.0343 (13)	0.0089 (10)	0.0045 (10)	0.0051 (9)
C14	0.0299 (12)	0.0302 (11)	0.0215 (11)	−0.0028 (9)	0.0012 (9)	−0.0007 (8)
C15	0.0172 (10)	0.0271 (10)	0.0264 (11)	−0.0007 (8)	0.0074 (8)	−0.0006 (8)
C16	0.0221 (12)	0.0345 (12)	0.0446 (15)	0.0055 (10)	0.0046 (10)	0.0057 (10)
C17	0.0244 (13)	0.0469 (14)	0.0515 (16)	−0.0041 (11)	0.0191 (11)	0.0086 (12)
C18	0.0283 (13)	0.0498 (15)	0.0394 (15)	0.0007 (12)	−0.0022 (11)	−0.0166 (12)
C19	0.0281 (11)	0.0186 (9)	0.0201 (10)	0.0026 (8)	0.0074 (8)	−0.0023 (7)
C20	0.0290 (13)	0.0414 (13)	0.0372 (14)	−0.0004 (11)	0.0025 (10)	−0.0145 (11)
C21	0.0392 (14)	0.0184 (9)	0.0279 (11)	0.0038 (9)	0.0131 (10)	−0.0032 (8)
C22	0.0594 (17)	0.0269 (11)	0.0195 (11)	0.0117 (11)	0.0125 (11)	0.0014 (8)
Cl1	0.0641 (4)	0.0222 (2)	0.0437 (3)	−0.0029 (3)	0.0417 (3)	0.0040 (2)
O1	0.0222 (7)	0.0135 (6)	0.0211 (7)	0.0052 (5)	0.0120 (6)	0.0042 (5)
O2	0.0329 (9)	0.0173 (6)	0.0297 (8)	0.0041 (6)	0.0217 (7)	0.0064 (6)
O3	0.0218 (7)	0.0152 (6)	0.0243 (7)	0.0046 (5)	0.0143 (6)	0.0030 (5)
P1	0.0197 (3)	0.0121 (2)	0.0163 (2)	0.00103 (18)	0.00787 (19)	0.00132 (16)
P2	0.0180 (3)	0.0148 (2)	0.0172 (2)	0.00112 (18)	0.00937 (19)	−0.00010 (17)
Pt1	0.02031 (4)	0.01324 (4)	0.01583 (4)	0.00074 (3)	0.01022 (3)	0.00099 (2)

Geometric parameters (Å, º)

C1—C2	1.390 (3)	C14—H14A	0.9800
C1—C6	1.393 (2)	C14—H14B	0.9800
C1—Pt1	1.9841 (18)	C14—H14C	0.9800
C2—C3	1.384 (3)	C15—C17	1.530 (3)
C2—O1	1.390 (2)	C15—C16	1.531 (3)
C3—C4	1.395 (2)	C15—C18	1.538 (3)
C3—H3	0.9500	C15—P2	1.852 (2)
C4—O2	1.372 (2)	C16—H16A	0.9800
C4—C5	1.389 (3)	C16—H16B	0.9800
C5—C6	1.387 (3)	C16—H16C	0.9800
C5—H5	0.9500	C17—H17A	0.9800
C6—O3	1.390 (2)	C17—H17B	0.9800
C7—C9	1.531 (3)	C17—H17C	0.9800
C7—C10	1.532 (3)	C18—H18A	0.9800
C7—C8	1.543 (3)	C18—H18B	0.9800
C7—P1	1.854 (2)	C18—H18C	0.9800
C8—H8A	0.9800	C19—C21	1.527 (3)
C8—H8B	0.9800	C19—C22	1.536 (3)
C8—H8C	0.9800	C19—C20	1.537 (3)
C9—H9A	0.9800	C19—P2	1.855 (2)
C9—H9B	0.9800	C20—H20A	0.9800
C9—H9C	0.9800	C20—H20B	0.9800
C10—H10A	0.9800	C20—H20C	0.9800
C10—H10B	0.9800	C21—H21A	0.9800
C10—H10C	0.9800	C21—H21B	0.9800
C11—C13	1.535 (3)	C21—H21C	0.9800
C11—C12	1.537 (3)	C22—H22A	0.9800
C11—C14	1.539 (3)	C22—H22B	0.9800
C11—P1	1.857 (2)	C22—H22C	0.9800
C12—H12A	0.9800	Cl1—Pt1	2.3907 (5)
C12—H12B	0.9800	O1—P1	1.6514 (13)
C12—H12C	0.9800	O2—H2	0.82 (3)
C13—H13A	0.9800	O3—P2	1.6514 (13)
C13—H13B	0.9800	P1—Pt1	2.2781 (5)
C13—H13C	0.9800	P2—Pt1	2.2796 (5)
C2—C1—C6	116.32 (16)	C16—C15—C18	108.19 (19)
C2—C1—Pt1	121.64 (13)	C17—C15—P2	110.18 (16)
C6—C1—Pt1	122.03 (14)	C16—C15—P2	114.05 (15)
C3—C2—O1	118.22 (16)	C18—C15—P2	104.48 (15)
C3—C2—C1	123.37 (17)	C15—C16—H16A	109.5
O1—C2—C1	118.41 (16)	C15—C16—H16B	109.5
C2—C3—C4	117.77 (17)	H16A—C16—H16B	109.5
C2—C3—H3	121.1	C15—C16—H16C	109.5
C4—C3—H3	121.1	H16A—C16—H16C	109.5
O2—C4—C5	116.91 (16)	H16B—C16—H16C	109.5
O2—C4—C3	121.65 (17)	C15—C17—H17A	109.5
C5—C4—C3	121.45 (17)	C15—C17—H17B	109.5
C6—C5—C4	118.14 (17)	H17A—C17—H17B	109.5
C6—C5—H5	120.9	C15—C17—H17C	109.5
C4—C5—H5	120.9	H17A—C17—H17C	109.5
C5—C6—O3	119.03 (16)	H17B—C17—H17C	109.5
C5—C6—C1	122.91 (17)	C15—C18—H18A	109.5
O3—C6—C1	118.06 (16)	C15—C18—H18B	109.5
C9—C7—C10	110.27 (18)	H18A—C18—H18B	109.5
C9—C7—C8	108.8 (2)	C15—C18—H18C	109.5
C10—C7—C8	108.90 (19)	H18A—C18—H18C	109.5
C9—C7—P1	110.74 (15)	H18B—C18—H18C	109.5
C10—C7—P1	113.09 (15)	C21—C19—C22	110.59 (18)
C8—C7—P1	104.80 (14)	C21—C19—C20	109.09 (18)
C7—C8—H8A	109.5	C22—C19—C20	109.2 (2)
C7—C8—H8B	109.5	C21—C19—P2	113.26 (15)
H8A—C8—H8B	109.5	C22—C19—P2	108.89 (14)
C7—C8—H8C	109.5	C20—C19—P2	105.68 (14)
H8A—C8—H8C	109.5	C19—C20—H20A	109.5
H8B—C8—H8C	109.5	C19—C20—H20B	109.5
C7—C9—H9A	109.5	H20A—C20—H20B	109.5
C7—C9—H9B	109.5	C19—C20—H20C	109.5
H9A—C9—H9B	109.5	H20A—C20—H20C	109.5
C7—C9—H9C	109.5	H20B—C20—H20C	109.5
H9A—C9—H9C	109.5	C19—C21—H21A	109.5
H9B—C9—H9C	109.5	C19—C21—H21B	109.5
C7—C10—H10A	109.5	H21A—C21—H21B	109.5
C7—C10—H10B	109.5	C19—C21—H21C	109.5
H10A—C10—H10B	109.5	H21A—C21—H21C	109.5
C7—C10—H10C	109.5	H21B—C21—H21C	109.5
H10A—C10—H10C	109.5	C19—C22—H22A	109.5
H10B—C10—H10C	109.5	C19—C22—H22B	109.5
C13—C11—C12	111.28 (18)	H22A—C22—H22B	109.5
C13—C11—C14	108.47 (18)	C19—C22—H22C	109.5
C12—C11—C14	108.90 (18)	H22A—C22—H22C	109.5
C13—C11—P1	113.03 (15)	H22B—C22—H22C	109.5
C12—C11—P1	109.56 (15)	C2—O1—P1	115.03 (11)
C14—C11—P1	105.35 (14)	C4—O2—H2	110.2 (19)
C11—C12—H12A	109.5	C6—O3—P2	114.89 (11)
C11—C12—H12B	109.5	O1—P1—C7	101.18 (8)
H12A—C12—H12B	109.5	O1—P1—C11	100.58 (8)
C11—C12—H12C	109.5	C7—P1—C11	114.96 (9)
H12A—C12—H12C	109.5	O1—P1—Pt1	104.36 (5)
H12B—C12—H12C	109.5	C7—P1—Pt1	116.95 (7)
C11—C13—H13A	109.5	C11—P1—Pt1	115.35 (7)
C11—C13—H13B	109.5	O3—P2—C15	101.07 (9)
H13A—C13—H13B	109.5	O3—P2—C19	101.36 (8)
C11—C13—H13C	109.5	C15—P2—C19	114.56 (10)
H13A—C13—H13C	109.5	O3—P2—Pt1	104.54 (5)
H13B—C13—H13C	109.5	C15—P2—Pt1	116.74 (7)
C11—C14—H14A	109.5	C19—P2—Pt1	115.39 (7)
C11—C14—H14B	109.5	C1—Pt1—P1	80.54 (5)
H14A—C14—H14B	109.5	C1—Pt1—P2	80.20 (5)
C11—C14—H14C	109.5	P1—Pt1—P2	160.676 (17)
H14A—C14—H14C	109.5	C1—Pt1—Cl1	178.95 (6)
H14B—C14—H14C	109.5	P1—Pt1—Cl1	99.023 (19)
C17—C15—C16	110.49 (19)	P2—Pt1—Cl1	100.257 (19)
C17—C15—C18	109.2 (2)
C6—C1—C2—C3	−0.9 (3)	C8—C7—P1—Pt1	55.81 (16)
Pt1—C1—C2—C3	178.98 (15)	C13—C11—P1—O1	−38.88 (16)
C6—C1—C2—O1	178.89 (16)	C12—C11—P1—O1	−163.60 (15)
Pt1—C1—C2—O1	−1.2 (2)	C14—C11—P1—O1	79.40 (15)
O1—C2—C3—C4	−177.85 (17)	C13—C11—P1—C7	68.85 (17)
C1—C2—C3—C4	2.0 (3)	C12—C11—P1—C7	−55.87 (18)
C2—C3—C4—O2	179.05 (18)	C14—C11—P1—C7	−172.87 (14)
C2—C3—C4—C5	−1.0 (3)	C13—C11—P1—Pt1	−150.45 (13)
O2—C4—C5—C6	179.09 (18)	C12—C11—P1—Pt1	84.83 (15)
C3—C4—C5—C6	−0.8 (3)	C14—C11—P1—Pt1	−32.18 (16)
C4—C5—C6—O3	−177.37 (17)	C6—O3—P2—C15	−127.19 (14)
C4—C5—C6—C1	2.0 (3)	C6—O3—P2—C19	114.69 (14)
C2—C1—C6—C5	−1.1 (3)	C6—O3—P2—Pt1	−5.57 (14)
Pt1—C1—C6—C5	178.99 (15)	C17—C15—P2—O3	−163.37 (16)
C2—C1—C6—O3	178.22 (17)	C16—C15—P2—O3	−38.44 (17)
Pt1—C1—C6—O3	−1.7 (2)	C18—C15—P2—O3	79.49 (17)
C3—C2—O1—P1	−178.45 (14)	C17—C15—P2—C19	−55.30 (19)
C1—C2—O1—P1	1.7 (2)	C16—C15—P2—C19	69.62 (18)
C5—C6—O3—P2	−175.52 (15)	C18—C15—P2—C19	−172.45 (16)
C1—C6—O3—P2	5.1 (2)	C17—C15—P2—Pt1	83.99 (16)
C2—O1—P1—C7	120.46 (14)	C16—C15—P2—Pt1	−151.09 (14)
C2—O1—P1—C11	−121.21 (13)	C18—C15—P2—Pt1	−33.16 (18)
C2—O1—P1—Pt1	−1.38 (13)	C21—C19—P2—O3	66.03 (17)
C9—C7—P1—O1	−173.96 (16)	C22—C19—P2—O3	−170.48 (15)
C10—C7—P1—O1	61.70 (17)	C20—C19—P2—O3	−53.34 (16)
C8—C7—P1—O1	−56.78 (16)	C21—C19—P2—C15	−41.87 (19)
C9—C7—P1—C11	78.67 (19)	C22—C19—P2—C15	81.62 (17)
C10—C7—P1—C11	−45.66 (19)	C20—C19—P2—C15	−161.23 (15)
C8—C7—P1—C11	−164.15 (15)	C21—C19—P2—Pt1	178.29 (13)
C9—C7—P1—Pt1	−61.38 (18)	C22—C19—P2—Pt1	−58.23 (17)
C10—C7—P1—Pt1	174.29 (13)	C20—C19—P2—Pt1	58.92 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···Cl1^i	0.82 (3)	2.38 (3)	3.1874 (16)	170 (3)

Symmetry code: (i) x+1/2, −y+1/2, z−1/2.