Synthesis and crystal structures of three organoplatinum(II) complexes bearing natural aryl­olefin and quinoline derivatives

Chi, N.T.T.; Van Thong, P.; Thang, N.M.; Thao, P.N.; Van Meervelt, L.

doi:10.1107/S2056989024004572

Synthesis and crystal structures of three organoplatinum(II) complexes bearing natural arylolefin and quinoline derivatives

N. T. T. Chi, P. Van Thong, N. M. Thang, P. N. Thao and L. Van Meervelt

The synthesis and crystal structures of three organoplatinum(II) complexes bearing natural arylolefin and quinoline derivatives are reported.

Keywords: crystal structure; platinum(II) complex; quinoline; arylolefin; square-planar coordination.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989024004572/pk2707sup1.cif Contains datablocks I, II, III
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989024004572/pk2707Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989024004572/pk2707IIsup3.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989024004572/pk2707IIIsup4.hkl Contains datablock III

CCDC references: 2355693; 2355692; 2355691

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 100 K
R factor = 0.021
wR factor = 0.054
Data-to-parameter ratio = 14.8

Structure: II

Single-crystal X-ray study
T = 100 K
R factor = 0.033
wR factor = 0.070
Data-to-parameter ratio = 17.9

Structure: III

Single-crystal X-ray study
T = 114 K
R factor = 0.030
wR factor = 0.056
Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B
PLAT196_ALERT_1_B No TEMP record and _measurement_temperature .NE.        293 Degree
PLAT430_ALERT_2_B Short Inter D...A Contact  O12      ..O30      .       2.72 Ang.
                                                      x,y,z  =      1_555 Check

Alert level C
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ     Please Check
              Calc: C22 H21 N O5 Pt, 0.474(O)
              Rep.: C22 H21 N O5 Pt, 0.47(O)
PLAT976_ALERT_2_C Check Calcd Resid. Dens.  0.72Ang From O30     .      -0.41 eA-3

Alert level G
PLAT012_ALERT_1_G No       _shelx_res_checksum Found in CIF ......     Please Check
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       6.35 Why ?
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd    2)       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd    2)       0.47 Check
PLAT311_ALERT_2_G Isolated Disordered Oxygen Atom (No H's ?) .....        O30 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O22      ..C21      .       2.92 Ang.
                                                1-x,2-y,1-z  =      3_676 Check
PLAT794_ALERT_5_G Tentative Bond Valency for Pt1       (II)      .       2.21 Info
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
                1  0  0,   0  0  2,
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       2.97 Note
              Predicted wR2: Based on SigI   2  1.83 or SHELX Weight  5.10       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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




Datablock: II


Alert level B
PLAT196_ALERT_1_B No TEMP record and _measurement_temperature .NE.        293 Degree

Alert level C
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.80Ang From Pt1             2.14 eA-3
PLAT972_ALERT_2_C Check Calcd Resid. Dens.  0.76Ang From Pt1            -1.75 eA-3
PLAT972_ALERT_2_C Check Calcd Resid. Dens.  0.76Ang From Pt1            -1.75 eA-3
PLAT973_ALERT_2_C Check Calcd Positive Resid. Density on       Pt1       1.17 eA-3
PLAT977_ALERT_2_C Check Negative Difference Density on H19B      .      -0.71 eA-3

Alert level G
PLAT012_ALERT_1_G No       _shelx_res_checksum Found in CIF ......     Please Check
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       5.07 Why ?
PLAT343_ALERT_2_G Unusual sp?      Angle Range in Main Residue for         C2 Check
PLAT794_ALERT_5_G Tentative Bond Valency for Pt1       (II)      .       2.13 Info
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
                0  2  0,   0  1  1,
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        524 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        4.5 Low
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       1.88 Note
              Predicted wR2: Based on SigI   2  3.72 or SHELX Weight  6.87       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check




Datablock: III



Alert level C
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        3.2 Ratio

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         32 Report
PLAT012_ALERT_1_G No       _shelx_res_checksum Found in CIF ......     Please Check
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Pt1A     --N3       .        6.3 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd    1)         3% Note
PLAT367_ALERT_2_G Long?  C(sp?)-C(sp?) Bond  C14      - C15      .       1.53 Ang.
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        288 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
                1  0  0,   1  1  0,   0  1  1,
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        1.9 Low
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       1.33 Note
              Predicted wR2: Based on SigI   2  4.17 or SHELX Weight  5.52       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 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
  11 ALERT level G = General information/check it is not something unexpected

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

Computing details top

[4-Methoxy-5-(2-methoxy-2-oxoethoxy)-2-(prop-2-en-1-yl)phenyl](quinolin-8-olato)platinum(II) (I) top

Crystal data top

[Pt(C₁₃H₁₅O₄)(C₉H₆NO)]	F(000) = 1127.2
M_r = 582.49	D_x = 1.961 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.1510 (4) Å	Cell parameters from 19506 reflections
b = 8.5584 (2) Å	θ = 2.9–29.0°
c = 18.2071 (6) Å	µ = 7.15 mm⁻¹
β = 105.714 (3)°	T = 100 K
V = 1972.65 (10) Å³	Plate, light brown
Z = 4	0.3 × 0.15 × 0.1 mm

Data collection top

SuperNova, Single source at offset, Eos diffractometer	4046 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	3672 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.039
Detector resolution: 15.9631 pixels mm^-1	θ_max = 26.4°, θ_min = 2.4°
ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022)	k = −10→10
T_min = 0.300, T_max = 1.000	l = −22→22
41833 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.021	H-atom parameters constrained
wR(F²) = 0.054	w = 1/[σ²(F_o²) + (0.0191P)² + 6.3477P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
4046 reflections	Δρ_max = 0.90 e Å⁻³
274 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	Occ. (<1)
Pt1	0.10321 (2)	0.48502 (2)	0.33132 (2)	0.01955 (6)
N2	−0.0487 (3)	0.4601 (4)	0.34836 (18)	0.0235 (7)
C3	−0.1264 (3)	0.3610 (5)	0.3186 (2)	0.0277 (9)
H3	−0.1190	0.2926	0.2807	0.033*
C4	−0.2193 (3)	0.3556 (5)	0.3422 (3)	0.0335 (10)
H4	−0.2720	0.2840	0.3202	0.040*
C5	−0.2325 (3)	0.4558 (5)	0.3975 (3)	0.0313 (9)
H5	−0.2937	0.4517	0.4136	0.038*
C6	−0.1525 (3)	0.5657 (5)	0.4300 (2)	0.0250 (8)
C7	−0.0605 (3)	0.5634 (4)	0.4035 (2)	0.0206 (7)
C8	−0.1587 (3)	0.6759 (5)	0.4861 (2)	0.0266 (9)
H8	−0.2177	0.6783	0.5050	0.032*
C9	−0.0776 (3)	0.7795 (5)	0.5129 (2)	0.0265 (9)
H9	−0.0828	0.8525	0.5496	0.032*
C10	0.0138 (3)	0.7779 (4)	0.4862 (2)	0.0216 (8)
H10	0.0672	0.8504	0.5049	0.026*
C11	0.0246 (3)	0.6696 (4)	0.4326 (2)	0.0199 (7)
O12	0.11072 (19)	0.6615 (3)	0.40694 (14)	0.0202 (5)
C13	0.2494 (3)	0.5222 (4)	0.3234 (2)	0.0217 (8)
C14	0.3317 (3)	0.5838 (5)	0.3820 (2)	0.0260 (8)
H14	0.3192	0.6096	0.4284	0.031*
C15	0.4312 (3)	0.6068 (5)	0.3723 (2)	0.0276 (8)
C16	0.4526 (3)	0.5653 (5)	0.3038 (2)	0.0261 (8)
C17	0.3717 (4)	0.5003 (5)	0.2454 (2)	0.0333 (10)
H17	0.3853	0.4708	0.1998	0.040*
C18	0.2703 (3)	0.4794 (5)	0.2550 (2)	0.0287 (9)
O19	0.5173 (2)	0.6665 (4)	0.42784 (16)	0.0332 (7)
C20	0.4963 (3)	0.7129 (5)	0.4966 (2)	0.0305 (9)
H20A	0.5622	0.7404	0.5334	0.037*
H20B	0.4657	0.6256	0.5172	0.037*
C21	0.4215 (3)	0.8507 (5)	0.4859 (2)	0.0314 (9)
O22	0.4065 (2)	0.9443 (4)	0.43373 (18)	0.0378 (7)
O23	0.3748 (2)	0.8571 (4)	0.54280 (19)	0.0391 (7)
C24	0.3069 (5)	0.9896 (6)	0.5401 (4)	0.0515 (14)
H24A	0.2574	0.9958	0.4905	0.077*
H24B	0.3486	1.0832	0.5496	0.077*
H24C	0.2692	0.9784	0.5782	0.077*
O25	0.5533 (2)	0.5945 (4)	0.29926 (17)	0.0372 (7)
C26	0.5731 (4)	0.5677 (7)	0.2266 (3)	0.0484 (13)
H26A	0.5261	0.6308	0.1886	0.073*
H26B	0.5615	0.4594	0.2132	0.073*
H26C	0.6448	0.5949	0.2294	0.073*
C27	0.1773 (4)	0.4205 (5)	0.1925 (2)	0.0351 (10)
H27A	0.1998	0.3353	0.1655	0.042*
H27B	0.1506	0.5038	0.1563	0.042*
C28	0.0905 (4)	0.3645 (5)	0.2267 (2)	0.0356 (10)
H28	0.0194	0.3587	0.1916	0.043*
C29	0.1124 (4)	0.2580 (5)	0.2867 (3)	0.0355 (10)
H29A	0.1808	0.2204	0.3062	0.043*
H29B	0.0588	0.2243	0.3072	0.043*
O30	0.1772 (6)	0.9369 (8)	0.3617 (4)	0.043 (3)	0.474 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.02183 (8)	0.01695 (8)	0.02025 (8)	−0.00247 (5)	0.00636 (6)	−0.00315 (5)
N2	0.0254 (17)	0.0211 (16)	0.0221 (16)	−0.0012 (13)	0.0034 (13)	0.0037 (13)
C3	0.027 (2)	0.0211 (19)	0.031 (2)	−0.0032 (16)	0.0027 (17)	0.0019 (16)
C4	0.024 (2)	0.028 (2)	0.044 (3)	−0.0073 (17)	0.0023 (19)	0.0074 (19)
C5	0.020 (2)	0.031 (2)	0.043 (2)	−0.0008 (17)	0.0088 (18)	0.0131 (19)
C6	0.0229 (19)	0.0227 (19)	0.030 (2)	0.0037 (15)	0.0080 (16)	0.0129 (16)
C7	0.0220 (18)	0.0165 (17)	0.0231 (18)	0.0017 (14)	0.0058 (15)	0.0065 (14)
C8	0.025 (2)	0.027 (2)	0.032 (2)	0.0074 (16)	0.0144 (17)	0.0112 (17)
C9	0.033 (2)	0.024 (2)	0.026 (2)	0.0113 (17)	0.0139 (17)	0.0086 (16)
C10	0.027 (2)	0.0167 (18)	0.0210 (19)	0.0015 (15)	0.0065 (15)	0.0028 (14)
C11	0.0224 (18)	0.0157 (17)	0.0216 (18)	0.0031 (14)	0.0059 (15)	0.0055 (14)
O12	0.0213 (13)	0.0191 (13)	0.0217 (13)	−0.0015 (10)	0.0084 (10)	−0.0020 (10)
C13	0.0231 (19)	0.0185 (18)	0.0234 (19)	0.0023 (14)	0.0063 (15)	0.0007 (14)
C14	0.029 (2)	0.026 (2)	0.026 (2)	0.0003 (16)	0.0114 (17)	−0.0068 (16)
C15	0.026 (2)	0.028 (2)	0.029 (2)	0.0002 (16)	0.0074 (17)	−0.0045 (17)
C16	0.024 (2)	0.031 (2)	0.026 (2)	0.0091 (17)	0.0104 (16)	0.0040 (16)
C17	0.035 (2)	0.040 (3)	0.028 (2)	0.0075 (19)	0.0138 (19)	−0.0071 (18)
C18	0.034 (2)	0.026 (2)	0.028 (2)	0.0000 (17)	0.0120 (18)	−0.0068 (16)
O19	0.0257 (15)	0.0421 (18)	0.0327 (16)	−0.0013 (13)	0.0093 (12)	−0.0056 (13)
C20	0.030 (2)	0.030 (2)	0.030 (2)	−0.0008 (17)	0.0057 (17)	−0.0048 (17)
C21	0.028 (2)	0.033 (2)	0.035 (2)	−0.0085 (18)	0.0109 (18)	−0.0052 (19)
O22	0.0391 (18)	0.0350 (17)	0.0384 (18)	−0.0060 (14)	0.0092 (14)	0.0021 (14)
O23	0.0390 (18)	0.0357 (18)	0.0486 (19)	0.0007 (14)	0.0220 (15)	−0.0002 (15)
C24	0.056 (3)	0.043 (3)	0.065 (4)	0.009 (2)	0.032 (3)	0.004 (2)
O25	0.0225 (15)	0.061 (2)	0.0305 (16)	0.0052 (14)	0.0120 (12)	0.0008 (15)
C26	0.027 (2)	0.089 (4)	0.035 (3)	0.010 (3)	0.017 (2)	0.002 (3)
C27	0.040 (3)	0.035 (2)	0.031 (2)	−0.004 (2)	0.0107 (19)	−0.0076 (19)
C28	0.040 (3)	0.039 (3)	0.031 (2)	−0.016 (2)	0.0144 (19)	−0.0216 (19)
C29	0.036 (2)	0.027 (2)	0.046 (3)	−0.0042 (18)	0.015 (2)	−0.0167 (19)
O30	0.043 (4)	0.033 (4)	0.051 (5)	0.001 (3)	0.008 (3)	−0.009 (3)

Geometric parameters (Å, º) top

Pt1—N2	2.114 (3)	C15—O19	1.395 (5)
Pt1—O12	2.028 (2)	C16—C17	1.399 (6)
Pt1—C13	1.993 (4)	C16—O25	1.372 (5)
Pt1—C28	2.132 (4)	C17—H17	0.9300
Pt1—C29	2.123 (4)	C17—C18	1.402 (6)
N2—C3	1.326 (5)	C18—C27	1.513 (6)
N2—C7	1.377 (5)	O19—C20	1.411 (5)
C3—H3	0.9300	C20—H20A	0.9700
C3—C4	1.401 (6)	C20—H20B	0.9700
C4—H4	0.9300	C20—C21	1.514 (6)
C4—C5	1.369 (6)	C21—O22	1.217 (5)
C5—H5	0.9300	C21—O23	1.341 (5)
C5—C6	1.416 (6)	O23—C24	1.436 (6)
C6—C7	1.420 (5)	C24—H24A	0.9600
C6—C8	1.409 (6)	C24—H24B	0.9600
C7—C11	1.427 (5)	C24—H24C	0.9600
C8—H8	0.9300	O25—C26	1.434 (5)
C8—C9	1.371 (6)	C26—H26A	0.9600
C9—H9	0.9300	C26—H26B	0.9600
C9—C10	1.414 (5)	C26—H26C	0.9600
C10—H10	0.9300	C27—H27A	0.9700
C10—C11	1.381 (5)	C27—H27B	0.9700
C11—O12	1.339 (4)	C27—C28	1.519 (6)
C13—C14	1.401 (5)	C28—H28	0.9800
C13—C18	1.394 (5)	C28—C29	1.391 (7)
C14—H14	0.9300	C29—H29A	0.9300
C14—C15	1.382 (5)	C29—H29B	0.9300
C15—C16	1.396 (5)

N2—Pt1—C28	103.50 (15)	O25—C16—C15	116.0 (4)
N2—Pt1—C29	96.79 (15)	O25—C16—C17	125.1 (4)
O12—Pt1—N2	81.35 (11)	C16—C17—H17	119.7
O12—Pt1—C28	160.78 (15)	C16—C17—C18	120.6 (4)
O12—Pt1—C29	160.82 (15)	C18—C17—H17	119.7
C13—Pt1—N2	174.70 (14)	C13—C18—C17	120.1 (4)
C13—Pt1—O12	93.43 (13)	C13—C18—C27	116.4 (4)
C13—Pt1—C28	81.74 (16)	C17—C18—C27	123.4 (4)
C13—Pt1—C29	87.83 (16)	C15—O19—C20	115.6 (3)
C29—Pt1—C28	38.17 (18)	O19—C20—H20A	109.1
C3—N2—Pt1	131.3 (3)	O19—C20—H20B	109.1
C3—N2—C7	118.8 (3)	O19—C20—C21	112.4 (3)
C7—N2—Pt1	109.8 (2)	H20A—C20—H20B	107.9
N2—C3—H3	118.8	C21—C20—H20A	109.1
N2—C3—C4	122.4 (4)	C21—C20—H20B	109.1
C4—C3—H3	118.8	O22—C21—C20	125.1 (4)
C3—C4—H4	120.0	O22—C21—O23	124.4 (4)
C5—C4—C3	120.0 (4)	O23—C21—C20	110.5 (4)
C5—C4—H4	120.0	C21—O23—C24	114.6 (4)
C4—C5—H5	120.1	O23—C24—H24A	109.5
C4—C5—C6	119.7 (4)	O23—C24—H24B	109.5
C6—C5—H5	120.1	O23—C24—H24C	109.5
C5—C6—C7	117.0 (4)	H24A—C24—H24B	109.5
C8—C6—C5	124.5 (4)	H24A—C24—H24C	109.5
C8—C6—C7	118.5 (4)	H24B—C24—H24C	109.5
N2—C7—C6	122.1 (3)	C16—O25—C26	116.4 (3)
N2—C7—C11	116.6 (3)	O25—C26—H26A	109.5
C6—C7—C11	121.3 (4)	O25—C26—H26B	109.5
C6—C8—H8	120.0	O25—C26—H26C	109.5
C9—C8—C6	119.9 (4)	H26A—C26—H26B	109.5
C9—C8—H8	120.0	H26A—C26—H26C	109.5
C8—C9—H9	119.2	H26B—C26—H26C	109.5
C8—C9—C10	121.5 (4)	C18—C27—H27A	109.7
C10—C9—H9	119.2	C18—C27—H27B	109.7
C9—C10—H10	119.7	C18—C27—C28	110.0 (4)
C11—C10—C9	120.6 (4)	H27A—C27—H27B	108.2
C11—C10—H10	119.7	C28—C27—H27A	109.7
C10—C11—C7	118.0 (3)	C28—C27—H27B	109.7
O12—C11—C7	119.3 (3)	Pt1—C28—H28	116.0
O12—C11—C10	122.7 (3)	C27—C28—Pt1	109.1 (3)
C11—O12—Pt1	112.7 (2)	C27—C28—H28	116.0
C14—C13—Pt1	124.5 (3)	C29—C28—Pt1	70.5 (2)
C18—C13—Pt1	116.8 (3)	C29—C28—C27	120.6 (4)
C18—C13—C14	118.7 (4)	C29—C28—H28	116.0
C13—C14—H14	119.4	Pt1—C29—H29A	108.6
C15—C14—C13	121.2 (4)	Pt1—C29—H29B	90.1
C15—C14—H14	119.4	C28—C29—Pt1	71.3 (2)
C14—C15—C16	120.3 (4)	C28—C29—H29A	120.0
C14—C15—O19	124.7 (3)	C28—C29—H29B	120.0
O19—C15—C16	114.9 (3)	H29A—C29—H29B	120.0
C15—C16—C17	119.0 (4)

Pt1—N2—C3—C4	174.8 (3)	C10—C11—O12—Pt1	178.0 (3)
Pt1—N2—C7—C6	−176.0 (3)	C13—C14—C15—C16	−1.6 (6)
Pt1—N2—C7—C11	4.4 (4)	C13—C14—C15—O19	−179.6 (4)
Pt1—C13—C14—C15	−179.8 (3)	C13—C18—C27—C28	−21.0 (5)
Pt1—C13—C18—C17	−179.3 (3)	C14—C13—C18—C17	−1.0 (6)
Pt1—C13—C18—C27	4.3 (5)	C14—C13—C18—C27	−177.4 (4)
N2—C3—C4—C5	0.5 (6)	C14—C15—C16—C17	0.1 (6)
N2—C7—C11—C10	178.1 (3)	C14—C15—C16—O25	179.2 (4)
N2—C7—C11—O12	−1.6 (5)	C14—C15—O19—C20	−3.5 (6)
C3—N2—C7—C6	0.8 (5)	C15—C16—C17—C18	1.0 (6)
C3—N2—C7—C11	−178.8 (3)	C15—C16—O25—C26	−173.7 (4)
C3—C4—C5—C6	0.7 (6)	C15—O19—C20—C21	−65.7 (5)
C4—C5—C6—C7	−1.1 (6)	C16—C15—O19—C20	178.4 (4)
C4—C5—C6—C8	178.8 (4)	C16—C17—C18—C13	−0.5 (6)
C5—C6—C7—N2	0.4 (5)	C16—C17—C18—C27	175.6 (4)
C5—C6—C7—C11	179.9 (3)	C17—C16—O25—C26	5.4 (6)
C5—C6—C8—C9	−178.8 (4)	C17—C18—C27—C28	162.8 (4)
C6—C7—C11—C10	−1.5 (5)	C18—C13—C14—C15	2.0 (6)
C6—C7—C11—O12	178.8 (3)	C18—C27—C28—Pt1	26.3 (5)
C6—C8—C9—C10	−0.7 (6)	C18—C27—C28—C29	−51.9 (5)
C7—N2—C3—C4	−1.2 (6)	O19—C15—C16—C17	178.3 (4)
C7—C6—C8—C9	1.1 (5)	O19—C15—C16—O25	−2.6 (5)
C7—C11—O12—Pt1	−2.3 (4)	O19—C20—C21—O22	−22.6 (6)
C8—C6—C7—N2	−179.6 (3)	O19—C20—C21—O23	158.3 (3)
C8—C6—C7—C11	0.0 (5)	C20—C21—O23—C24	176.5 (4)
C8—C9—C10—C11	−0.8 (6)	O22—C21—O23—C24	−2.6 (6)
C9—C10—C11—C7	1.9 (5)	O25—C16—C17—C18	−178.1 (4)
C9—C10—C11—O12	−178.4 (3)	C27—C28—C29—Pt1	101.2 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of ring C6–C11.

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27A···Cg1ⁱ	0.97	2.81	3.465 (4)	125

Symmetry code: (i) −x, y−1/2, −z+1/2.

[4-Methoxy-5-(2-oxo-2-propoxyethoxy)-2-(prop-2-en-1-yl)phenyl](quinoline-2-carboxylato)platinum(II) (II) top

Crystal data top

[Pt(C₁₅H₁₉O₄)(C₁₀H6NO₂)]	F(000) = 1232
M_r = 630.55	D_x = 1.910 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.2857 (4) Å	Cell parameters from 8290 reflections
b = 18.5001 (9) Å	θ = 2.9–29.0°
c = 14.6282 (7) Å	µ = 6.44 mm⁻¹
β = 102.014 (5)°	T = 100 K
V = 2193.18 (19) Å³	Block, orange
Z = 4	0.4 × 0.4 × 0.3 mm

Data collection top

SuperNova, Single source at offset, Eos diffractometer	5366 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	4652 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.057
Detector resolution: 15.9631 pixels mm^-1	θ_max = 29.1°, θ_min = 2.6°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022)	k = −25→24
T_min = 0.669, T_max = 1.000	l = −19→19
23965 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.070	w = 1/[σ²(F_o²) + (0.0204P)² + 5.0718P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.003
5366 reflections	Δρ_max = 2.16 e Å⁻³
300 parameters	Δρ_min = −1.73 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
Pt1	−0.05560 (2)	0.61639 (2)	0.09345 (2)	0.01722 (6)
C2	−0.3155 (5)	0.6274 (2)	0.0693 (3)	0.0219 (9)
H2A	−0.3776	0.6082	0.0108	0.026*
H2B	−0.3664	0.6180	0.1221	0.026*
C3	−0.2450 (5)	0.6967 (2)	0.0656 (3)	0.0204 (9)
H3	−0.2631	0.7194	0.0038	0.024*
C4	−0.2226 (6)	0.7476 (2)	0.1480 (3)	0.0233 (10)
H4A	−0.3286	0.7671	0.1538	0.028*
H4B	−0.1520	0.7875	0.1385	0.028*
C5	−0.1454 (5)	0.7072 (2)	0.2364 (3)	0.0183 (9)
C6	−0.0619 (5)	0.6442 (2)	0.2243 (3)	0.0164 (8)
C7	0.0167 (5)	0.6048 (2)	0.3027 (3)	0.0195 (9)
H7	0.0717	0.5621	0.2947	0.023*
C8	0.0134 (5)	0.6286 (2)	0.3922 (3)	0.0191 (9)
C9	−0.0748 (5)	0.6916 (2)	0.4044 (3)	0.0180 (9)
C10	−0.1524 (5)	0.7309 (2)	0.3268 (3)	0.0194 (9)
H10	−0.2091	0.7730	0.3347	0.023*
O11	−0.0792 (4)	0.70854 (15)	0.4954 (2)	0.0207 (6)
C12	−0.1635 (6)	0.7729 (2)	0.5106 (3)	0.0248 (10)
H12A	−0.1152	0.8133	0.4850	0.037*
H12B	−0.1546	0.7800	0.5765	0.037*
H12C	−0.2777	0.7689	0.4805	0.037*
O13	0.0916 (4)	0.59562 (16)	0.4739 (2)	0.0228 (7)
C14	0.1812 (6)	0.5321 (2)	0.4651 (3)	0.0219 (9)
H14A	0.2499	0.5392	0.4196	0.026*
H14B	0.1061	0.4924	0.4442	0.026*
C15	0.2864 (5)	0.5154 (2)	0.5592 (3)	0.0204 (9)
O16	0.3081 (4)	0.55414 (18)	0.6260 (2)	0.0335 (8)
O17	0.3562 (4)	0.45000 (16)	0.5567 (2)	0.0259 (7)
C18	0.4476 (6)	0.4221 (2)	0.6464 (3)	0.0262 (10)
H18A	0.3748	0.4161	0.6899	0.031*
H18B	0.5357	0.4550	0.6736	0.031*
C19	0.5177 (6)	0.3497 (2)	0.6249 (3)	0.0298 (11)
H19A	0.6013	0.3571	0.5883	0.036*
H19B	0.4307	0.3202	0.5886	0.036*
C20	0.5934 (6)	0.3109 (3)	0.7157 (3)	0.0348 (12)
H20A	0.6450	0.2670	0.7016	0.052*
H20B	0.5084	0.2997	0.7491	0.052*
H20C	0.6744	0.3415	0.7533	0.052*
N21	0.0072 (4)	0.59004 (18)	−0.0416 (2)	0.0165 (7)
C22	−0.0717 (6)	0.6046 (2)	−0.1330 (3)	0.0210 (9)
C23	−0.2406 (6)	0.6240 (2)	−0.1543 (3)	0.0229 (10)
H23	−0.2981	0.6286	−0.1063	0.027*
C24	−0.3208 (7)	0.6363 (2)	−0.2454 (3)	0.0295 (11)
H24	−0.4326	0.6477	−0.2585	0.035*
C25	−0.2346 (7)	0.6316 (2)	−0.3190 (3)	0.0301 (11)
H25	−0.2888	0.6408	−0.3802	0.036*
C26	−0.0716 (7)	0.6135 (2)	−0.2999 (3)	0.0272 (11)
H26	−0.0144	0.6117	−0.3482	0.033*
C27	0.0111 (6)	0.5975 (2)	−0.2081 (3)	0.0225 (10)
C28	0.1770 (6)	0.5718 (2)	−0.1873 (3)	0.0262 (10)
H28	0.2359	0.5675	−0.2346	0.031*
C29	0.2488 (6)	0.5537 (2)	−0.0978 (3)	0.0228 (10)
H29	0.3547	0.5344	−0.0840	0.027*
C30	0.1604 (5)	0.5647 (2)	−0.0265 (3)	0.0201 (9)
C31	0.2456 (5)	0.5489 (2)	0.0731 (3)	0.0194 (9)
O32	0.3826 (4)	0.52108 (16)	0.0902 (2)	0.0251 (7)
O33	0.1638 (3)	0.56700 (16)	0.13703 (19)	0.0205 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.01864 (10)	0.01974 (10)	0.01431 (10)	0.00199 (6)	0.00582 (7)	0.00078 (6)
C2	0.019 (2)	0.024 (2)	0.023 (2)	0.0026 (18)	0.0041 (19)	−0.0017 (18)
C3	0.019 (2)	0.026 (2)	0.016 (2)	0.0077 (18)	0.0024 (17)	0.0028 (17)
C4	0.027 (2)	0.015 (2)	0.026 (2)	0.0021 (18)	0.002 (2)	−0.0026 (17)
C5	0.019 (2)	0.0157 (19)	0.019 (2)	−0.0028 (17)	0.0017 (17)	0.0021 (16)
C6	0.017 (2)	0.0179 (19)	0.016 (2)	−0.0012 (17)	0.0053 (16)	0.0001 (16)
C7	0.018 (2)	0.019 (2)	0.023 (2)	0.0052 (17)	0.0076 (18)	0.0005 (17)
C8	0.020 (2)	0.023 (2)	0.016 (2)	−0.0004 (18)	0.0055 (17)	0.0013 (17)
C9	0.019 (2)	0.0162 (19)	0.020 (2)	−0.0033 (17)	0.0058 (18)	−0.0026 (16)
C10	0.021 (2)	0.0148 (19)	0.022 (2)	0.0019 (17)	0.0044 (18)	−0.0035 (17)
O11	0.0299 (17)	0.0166 (14)	0.0164 (15)	0.0046 (13)	0.0064 (13)	−0.0026 (12)
C12	0.026 (2)	0.023 (2)	0.025 (2)	0.0059 (19)	0.005 (2)	−0.0056 (19)
O13	0.0315 (18)	0.0233 (15)	0.0135 (15)	0.0115 (14)	0.0043 (13)	0.0014 (12)
C14	0.028 (2)	0.021 (2)	0.019 (2)	0.0087 (19)	0.0093 (19)	0.0023 (17)
C15	0.023 (2)	0.022 (2)	0.019 (2)	0.0069 (18)	0.0114 (18)	0.0034 (17)
O16	0.045 (2)	0.0364 (19)	0.0175 (17)	0.0176 (17)	0.0040 (15)	−0.0044 (14)
O17	0.0318 (18)	0.0206 (16)	0.0248 (17)	0.0071 (14)	0.0050 (14)	0.0029 (13)
C18	0.029 (3)	0.030 (2)	0.021 (2)	0.007 (2)	0.0062 (19)	0.0090 (19)
C19	0.040 (3)	0.016 (2)	0.034 (3)	0.000 (2)	0.009 (2)	0.0036 (19)
C20	0.037 (3)	0.027 (3)	0.037 (3)	−0.002 (2)	0.001 (2)	0.007 (2)
N21	0.0200 (18)	0.0166 (17)	0.0143 (17)	0.0002 (14)	0.0067 (14)	0.0017 (13)
C22	0.030 (3)	0.0138 (19)	0.020 (2)	−0.0051 (18)	0.0066 (19)	−0.0021 (16)
C23	0.030 (3)	0.021 (2)	0.018 (2)	0.0016 (19)	0.007 (2)	−0.0034 (17)
C24	0.037 (3)	0.029 (2)	0.020 (2)	0.003 (2)	−0.002 (2)	0.0030 (19)
C25	0.050 (3)	0.020 (2)	0.017 (2)	0.002 (2)	0.001 (2)	0.0040 (18)
C26	0.044 (3)	0.019 (2)	0.020 (2)	−0.009 (2)	0.010 (2)	−0.0025 (17)
C27	0.036 (3)	0.0148 (19)	0.020 (2)	−0.0104 (19)	0.013 (2)	−0.0057 (17)
C28	0.037 (3)	0.023 (2)	0.024 (2)	−0.005 (2)	0.019 (2)	−0.0091 (19)
C29	0.023 (2)	0.021 (2)	0.027 (2)	−0.0051 (18)	0.011 (2)	−0.0051 (18)
C30	0.024 (2)	0.0136 (19)	0.025 (2)	−0.0048 (17)	0.0101 (19)	−0.0045 (17)
C31	0.021 (2)	0.017 (2)	0.021 (2)	−0.0026 (17)	0.0062 (18)	−0.0045 (17)
O32	0.0193 (16)	0.0266 (17)	0.0302 (18)	0.0015 (14)	0.0067 (14)	−0.0010 (14)
O33	0.0195 (16)	0.0270 (16)	0.0147 (15)	0.0020 (13)	0.0034 (12)	−0.0008 (12)

Geometric parameters (Å, º) top

Pt1—C2	2.118 (4)	C15—O17	1.345 (5)
Pt1—C3	2.138 (4)	O17—C18	1.466 (5)
Pt1—C6	1.993 (4)	C18—H18A	0.9700
Pt1—N21	2.200 (3)	C18—H18B	0.9700
Pt1—O33	2.016 (3)	C18—C19	1.519 (6)
C2—H2A	0.9700	C19—H19A	0.9700
C2—H2B	0.9700	C19—H19B	0.9700
C2—C3	1.413 (6)	C19—C20	1.524 (6)
C3—H3	0.9800	C20—H20A	0.9600
C3—C4	1.511 (6)	C20—H20B	0.9600
C4—H4A	0.9700	C20—H20C	0.9600
C4—H4B	0.9700	N21—C22	1.387 (5)
C4—C5	1.515 (6)	N21—C30	1.328 (5)
C5—C6	1.385 (6)	C22—C23	1.415 (6)
C5—C10	1.406 (6)	C22—C27	1.417 (6)
C6—C7	1.400 (6)	C23—H23	0.9300
C7—H7	0.9300	C23—C24	1.378 (6)
C7—C8	1.387 (6)	C24—H24	0.9300
C8—C9	1.407 (6)	C24—C25	1.413 (7)
C8—O13	1.378 (5)	C25—H25	0.9300
C9—C10	1.388 (6)	C25—C26	1.362 (7)
C9—O11	1.375 (5)	C26—H26	0.9300
C10—H10	0.9300	C26—C27	1.405 (6)
O11—C12	1.422 (5)	C27—C28	1.425 (7)
C12—H12A	0.9600	C28—H28	0.9300
C12—H12B	0.9600	C28—C29	1.363 (6)
C12—H12C	0.9600	C29—H29	0.9300
O13—C14	1.411 (5)	C29—C30	1.407 (6)
C14—H14A	0.9700	C30—C31	1.510 (6)
C14—H14B	0.9700	C31—O32	1.224 (5)
C14—C15	1.500 (6)	C31—O33	1.307 (5)
C15—O16	1.195 (5)

C2—Pt1—C3	38.79 (16)	C15—C14—H14A	110.2
C2—Pt1—N21	107.11 (15)	C15—C14—H14B	110.2
C3—Pt1—N21	106.53 (14)	O16—C15—C14	125.9 (4)
C6—Pt1—C2	84.62 (17)	O16—C15—O17	124.7 (4)
C6—Pt1—C3	80.72 (16)	O17—C15—C14	109.4 (4)
C6—Pt1—N21	167.94 (15)	C15—O17—C18	115.9 (3)
C6—Pt1—O33	90.88 (14)	O17—C18—H18A	110.6
O33—Pt1—C2	156.21 (14)	O17—C18—H18B	110.6
O33—Pt1—C3	162.41 (14)	O17—C18—C19	105.9 (4)
O33—Pt1—N21	79.46 (12)	H18A—C18—H18B	108.7
Pt1—C2—H2A	116.5	C19—C18—H18A	110.6
Pt1—C2—H2B	116.5	C19—C18—H18B	110.6
H2A—C2—H2B	113.5	C18—C19—H19A	109.7
C3—C2—Pt1	71.3 (2)	C18—C19—H19B	109.7
C3—C2—H2A	116.5	C18—C19—C20	109.9 (4)
C3—C2—H2B	116.5	H19A—C19—H19B	108.2
Pt1—C3—H3	116.0	C20—C19—H19A	109.7
C2—C3—Pt1	69.9 (2)	C20—C19—H19B	109.7
C2—C3—H3	116.0	C19—C20—H20A	109.5
C2—C3—C4	121.2 (4)	C19—C20—H20B	109.5
C4—C3—Pt1	108.5 (3)	C19—C20—H20C	109.5
C4—C3—H3	116.0	H20A—C20—H20B	109.5
C3—C4—H4A	109.8	H20A—C20—H20C	109.5
C3—C4—H4B	109.8	H20B—C20—H20C	109.5
C3—C4—C5	109.5 (3)	C22—N21—Pt1	132.1 (3)
H4A—C4—H4B	108.2	C30—N21—Pt1	109.0 (3)
C5—C4—H4A	109.8	C30—N21—C22	118.1 (4)
C5—C4—H4B	109.8	N21—C22—C23	120.5 (4)
C6—C5—C4	116.1 (4)	N21—C22—C27	121.4 (4)
C6—C5—C10	120.1 (4)	C23—C22—C27	118.0 (4)
C10—C5—C4	123.8 (4)	C22—C23—H23	119.7
C5—C6—Pt1	117.0 (3)	C24—C23—C22	120.6 (4)
C5—C6—C7	119.6 (4)	C24—C23—H23	119.7
C7—C6—Pt1	123.5 (3)	C23—C24—H24	119.7
C6—C7—H7	119.7	C23—C24—C25	120.5 (5)
C8—C7—C6	120.7 (4)	C25—C24—H24	119.7
C8—C7—H7	119.7	C24—C25—H25	120.2
C7—C8—C9	119.8 (4)	C26—C25—C24	119.7 (4)
O13—C8—C7	125.5 (4)	C26—C25—H25	120.2
O13—C8—C9	114.8 (4)	C25—C26—H26	119.5
C10—C9—C8	119.6 (4)	C25—C26—C27	120.9 (5)
O11—C9—C8	115.6 (4)	C27—C26—H26	119.5
O11—C9—C10	124.8 (4)	C22—C27—C28	117.8 (4)
C5—C10—H10	119.9	C26—C27—C22	120.1 (5)
C9—C10—C5	120.2 (4)	C26—C27—C28	122.1 (4)
C9—C10—H10	119.9	C27—C28—H28	120.1
C9—O11—C12	117.1 (3)	C29—C28—C27	119.7 (4)
O11—C12—H12A	109.5	C29—C28—H28	120.1
O11—C12—H12B	109.5	C28—C29—H29	120.5
O11—C12—H12C	109.5	C28—C29—C30	119.1 (4)
H12A—C12—H12B	109.5	C30—C29—H29	120.5
H12A—C12—H12C	109.5	N21—C30—C29	123.7 (4)
H12B—C12—H12C	109.5	N21—C30—C31	117.8 (4)
C8—O13—C14	116.8 (3)	C29—C30—C31	118.5 (4)
O13—C14—H14A	110.2	O32—C31—C30	120.3 (4)
O13—C14—H14B	110.2	O32—C31—O33	124.0 (4)
O13—C14—C15	107.7 (3)	O33—C31—C30	115.7 (4)
H14A—C14—H14B	108.5	C31—O33—Pt1	117.2 (3)

Pt1—C2—C3—C4	−100.0 (4)	O13—C14—C15—O17	171.5 (3)
Pt1—C3—C4—C5	−30.0 (4)	C14—C15—O17—C18	−173.1 (4)
Pt1—C6—C7—C8	177.3 (3)	C15—O17—C18—C19	−178.4 (4)
Pt1—N21—C22—C23	−18.3 (6)	O16—C15—O17—C18	8.0 (6)
Pt1—N21—C22—C27	164.5 (3)	O17—C18—C19—C20	−171.5 (4)
Pt1—N21—C30—C29	−169.3 (3)	N21—C22—C23—C24	−177.9 (4)
Pt1—N21—C30—C31	8.9 (4)	N21—C22—C27—C26	−179.2 (4)
C2—C3—C4—C5	47.2 (5)	N21—C22—C27—C28	2.6 (6)
C3—C4—C5—C6	21.0 (5)	N21—C30—C31—O32	175.2 (4)
C3—C4—C5—C10	−160.3 (4)	N21—C30—C31—O33	−5.0 (5)
C4—C5—C6—Pt1	0.0 (5)	C22—N21—C30—C29	1.9 (6)
C4—C5—C6—C7	178.3 (4)	C22—N21—C30—C31	−180.0 (3)
C4—C5—C10—C9	−178.3 (4)	C22—C23—C24—C25	−1.8 (7)
C5—C6—C7—C8	−0.8 (6)	C22—C27—C28—C29	1.4 (6)
C6—C5—C10—C9	0.4 (6)	C23—C22—C27—C26	3.5 (6)
C6—C7—C8—C9	2.4 (6)	C23—C22—C27—C28	−174.7 (4)
C6—C7—C8—O13	−177.4 (4)	C23—C24—C25—C26	1.2 (7)
C7—C8—C9—C10	−2.5 (6)	C24—C25—C26—C27	1.7 (7)
C7—C8—C9—O11	176.3 (4)	C25—C26—C27—C22	−4.1 (6)
C7—C8—O13—C14	−0.4 (6)	C25—C26—C27—C28	174.0 (4)
C8—C9—C10—C5	1.2 (6)	C26—C27—C28—C29	−176.7 (4)
C8—C9—O11—C12	178.3 (4)	C27—C22—C23—C24	−0.6 (6)
C8—O13—C14—C15	167.0 (4)	C27—C28—C29—C30	−3.6 (6)
C9—C8—O13—C14	179.8 (4)	C28—C29—C30—N21	2.0 (6)
C10—C5—C6—Pt1	−178.8 (3)	C28—C29—C30—C31	−176.1 (4)
C10—C5—C6—C7	−0.5 (6)	C29—C30—C31—O32	−6.5 (6)
C10—C9—O11—C12	−2.9 (6)	C29—C30—C31—O33	173.3 (4)
O11—C9—C10—C5	−177.5 (4)	C30—N21—C22—C23	173.0 (4)
O13—C8—C9—C10	177.3 (4)	C30—N21—C22—C27	−4.2 (6)
O13—C8—C9—O11	−4.0 (5)	C30—C31—O33—Pt1	−2.6 (4)
O13—C14—C15—O16	−9.7 (6)	O32—C31—O33—Pt1	177.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of rings C5–C10 and C22–C27, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20C···O33ⁱ	0.96	2.52	3.462 (6)	168
C28—H28···O16ⁱⁱ	0.93	2.26	3.159 (5)	164
C29—H29···O32ⁱⁱⁱ	0.93	2.43	3.334 (6)	166
C18—H18A···Cg1^iv	0.97	2.97	3.711 (5)	134
C20—H20A···Cg2^v	0.96	2.78	3.605 (6)	144

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

Chlorido[4-methoxy-5-(2-oxo-2-propoxyethoxy)-2-(prop-2-en-1-yl)phenyl]\ (quinoline)platinum(II) (III) top

Crystal data top

[Pt(C₁₅H₁₉O₄)Cl(C₉H₇N)]	F(000) = 1216
M_r = 623.00	D_x = 1.833 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.576 (2) Å	Cell parameters from 3865 reflections
b = 11.0945 (9) Å	θ = 2.9–29.0°
c = 15.700 (2) Å	µ = 6.36 mm⁻¹
β = 117.197 (18)°	T = 114 K
V = 2258.1 (6) Å³	Block, colourless
Z = 4	0.27 × 0.2 × 0.16 mm

Data collection top

SuperNova, Single source at offset, Eos diffractometer	4603 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3885 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.028
Detector resolution: 15.9631 pixels mm^-1	θ_max = 26.4°, θ_min = 2.4°
ω scans	h = −9→18
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022)	k = −12→13
T_min = 0.579, T_max = 1.000	l = −19→19
8975 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.056	w = 1/[σ²(F_o²) + (0.0148P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
4603 reflections	Δρ_max = 0.85 e Å⁻³
292 parameters	Δρ_min = −1.07 e Å⁻³
288 restraints

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Pt1A	0.48946 (7)	0.89396 (12)	0.13147 (5)	0.02532 (15)	0.928 (7)
Pt1B	0.4763 (6)	0.8600 (18)	0.1469 (11)	0.028 (2)	0.072 (7)
Cl2	0.38195 (9)	0.97795 (9)	0.18873 (8)	0.0360 (3)
N3	0.6140 (3)	0.9769 (3)	0.2531 (2)	0.0344 (9)
C4	0.6343 (3)	1.0901 (3)	0.2431 (3)	0.0329 (10)
H4	0.6028	1.1231	0.1803	0.039*
C5	0.6988 (3)	1.1655 (4)	0.3182 (3)	0.0340 (10)
H5	0.7100	1.2471	0.3072	0.041*
C6	0.7452 (3)	1.1163 (4)	0.4087 (3)	0.0355 (11)
H6	0.7887	1.1645	0.4620	0.043*
C7	0.7282 (3)	0.9938 (3)	0.4222 (3)	0.0257 (9)
C8	0.7764 (3)	0.9375 (4)	0.5128 (3)	0.0389 (11)
H8	0.8211	0.9833	0.5672	0.047*
C9	0.7601 (4)	0.8201 (4)	0.5239 (3)	0.0437 (12)
H9	0.7944	0.7827	0.5850	0.052*
C10	0.6917 (3)	0.7542 (4)	0.4435 (3)	0.0370 (11)
H10	0.6798	0.6718	0.4516	0.044*
C11	0.6417 (3)	0.8035 (4)	0.3544 (3)	0.0327 (10)
H11	0.5950	0.7565	0.3018	0.039*
C12	0.6604 (3)	0.9264 (4)	0.3413 (3)	0.0285 (9)
C13	0.5817 (3)	0.8736 (4)	0.0623 (3)	0.0350 (11)
H13C	0.5462	0.8797	−0.0084	0.042*	0.928 (7)
H13D	0.6496	0.9145	0.0922	0.042*	0.928 (7)
H13A	0.5452	0.8820	−0.0082	0.042*	0.072 (7)
H13B	0.6476	0.9184	0.0940	0.042*	0.072 (7)
C14	0.5759 (3)	0.7628 (4)	0.1010 (3)	0.0329 (10)
H14A	0.6406	0.7350	0.1570	0.039*	0.928 (7)
H14	0.6423	0.7337	0.1542	0.039*	0.072 (7)
C15	0.5035 (3)	0.6634 (4)	0.0397 (3)	0.0346 (10)
H15A	0.5298	0.6288	−0.0030	0.042*
H15B	0.5005	0.5982	0.0814	0.042*
C16	0.3968 (3)	0.7144 (3)	−0.0195 (3)	0.0280 (9)
C17	0.3226 (3)	0.6564 (4)	−0.1006 (3)	0.0300 (10)
H17	0.3400	0.5851	−0.1234	0.036*
C18	0.2236 (3)	0.7023 (4)	−0.1478 (3)	0.0332 (10)
C19	0.2006 (3)	0.8102 (4)	−0.1163 (3)	0.0313 (10)
C20	0.2743 (3)	0.8681 (4)	−0.0358 (3)	0.0293 (10)
H20	0.2569	0.9412	−0.0152	0.035*
C21	0.3737 (3)	0.8207 (4)	0.0156 (3)	0.0271 (9)
O22	0.1425 (2)	0.6476 (3)	−0.2244 (2)	0.0414 (8)
C23	0.1632 (4)	0.5393 (4)	−0.2615 (3)	0.0449 (13)
H23A	0.0989	0.5085	−0.3134	0.067*
H23B	0.1921	0.4790	−0.2104	0.067*
H23C	0.2127	0.5560	−0.2862	0.067*
O24	0.1004 (2)	0.8561 (3)	−0.1605 (2)	0.0408 (8)
C25	0.0681 (3)	0.8996 (4)	−0.2554 (3)	0.0401 (11)
H25A	−0.0078	0.8928	−0.2920	0.048*
H25B	0.0988	0.8486	−0.2875	0.048*
C26	0.0989 (3)	1.0276 (4)	−0.2567 (3)	0.0400 (11)
O27	0.1496 (3)	1.0896 (3)	−0.1889 (2)	0.0551 (10)
O28	0.0592 (2)	1.0647 (3)	−0.3482 (2)	0.0442 (8)
C29	0.0798 (4)	1.1888 (4)	−0.3643 (3)	0.0493 (13)
H29A	0.1551	1.2023	−0.3376	0.059*
H29B	0.0521	1.2452	−0.3329	0.059*
C30	0.0280 (4)	1.2087 (5)	−0.4703 (4)	0.0563 (14)
H30A	−0.0463	1.1898	−0.4964	0.068*
H30B	0.0580	1.1533	−0.5004	0.068*
C31	0.0407 (5)	1.3383 (5)	−0.4953 (4)	0.082 (2)
H31A	0.0183	1.3446	−0.5642	0.123*
H31B	0.1133	1.3619	−0.4599	0.123*
H31C	−0.0015	1.3917	−0.4777	0.123*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1A	0.03098 (18)	0.0218 (3)	0.02215 (15)	−0.00439 (19)	0.01123 (11)	−0.00014 (15)
Pt1B	0.0265 (18)	0.025 (4)	0.034 (3)	−0.0041 (19)	0.0147 (16)	−0.008 (3)
Cl2	0.0431 (7)	0.0342 (6)	0.0336 (6)	−0.0016 (5)	0.0199 (5)	−0.0052 (5)
N3	0.043 (2)	0.0285 (18)	0.0320 (19)	−0.0023 (17)	0.0173 (17)	0.0005 (15)
C4	0.041 (3)	0.022 (2)	0.037 (2)	0.001 (2)	0.019 (2)	−0.0007 (18)
C5	0.046 (3)	0.024 (2)	0.041 (2)	−0.006 (2)	0.027 (2)	−0.0057 (19)
C6	0.039 (3)	0.033 (2)	0.040 (2)	−0.008 (2)	0.024 (2)	−0.0127 (19)
C7	0.028 (2)	0.024 (2)	0.028 (2)	−0.0006 (18)	0.0148 (18)	−0.0030 (17)
C8	0.036 (3)	0.042 (2)	0.034 (2)	0.002 (2)	0.012 (2)	0.001 (2)
C9	0.046 (3)	0.044 (3)	0.036 (3)	0.006 (2)	0.014 (2)	0.005 (2)
C10	0.044 (3)	0.035 (2)	0.034 (2)	0.000 (2)	0.019 (2)	0.0068 (19)
C11	0.039 (3)	0.030 (2)	0.031 (2)	−0.004 (2)	0.017 (2)	0.0006 (18)
C12	0.027 (2)	0.035 (2)	0.028 (2)	0.0028 (18)	0.0154 (18)	0.0003 (17)
C13	0.032 (2)	0.041 (2)	0.029 (2)	0.000 (2)	0.011 (2)	−0.006 (2)
C14	0.029 (2)	0.035 (2)	0.030 (2)	0.0054 (19)	0.010 (2)	−0.0046 (19)
C15	0.043 (3)	0.026 (2)	0.033 (2)	0.000 (2)	0.015 (2)	−0.0003 (19)
C16	0.032 (2)	0.023 (2)	0.030 (2)	−0.0052 (18)	0.0152 (18)	−0.0013 (17)
C17	0.039 (2)	0.025 (2)	0.032 (2)	−0.0077 (19)	0.0208 (19)	−0.0044 (18)
C18	0.036 (2)	0.037 (2)	0.027 (2)	−0.0155 (19)	0.0151 (19)	−0.0079 (19)
C19	0.028 (2)	0.044 (2)	0.026 (2)	−0.0048 (19)	0.0158 (18)	−0.0027 (19)
C20	0.035 (2)	0.031 (2)	0.027 (2)	−0.0017 (19)	0.0176 (18)	−0.0036 (18)
C21	0.031 (2)	0.026 (2)	0.027 (2)	−0.0050 (18)	0.0158 (17)	0.0036 (17)
O22	0.0353 (18)	0.0500 (18)	0.0359 (18)	−0.0150 (16)	0.0139 (15)	−0.0166 (15)
C23	0.050 (3)	0.048 (3)	0.038 (3)	−0.022 (3)	0.023 (3)	−0.017 (2)
O24	0.0267 (16)	0.063 (2)	0.0324 (17)	−0.0006 (15)	0.0134 (14)	−0.0076 (16)
C25	0.029 (2)	0.055 (3)	0.029 (2)	0.005 (2)	0.007 (2)	−0.009 (2)
C26	0.026 (2)	0.051 (3)	0.033 (2)	0.009 (2)	0.005 (2)	−0.010 (2)
O27	0.053 (2)	0.047 (2)	0.0369 (19)	0.0049 (18)	−0.0032 (18)	−0.0113 (16)
O28	0.0387 (19)	0.0484 (19)	0.0340 (18)	0.0061 (16)	0.0068 (15)	−0.0079 (15)
C29	0.043 (3)	0.045 (3)	0.048 (3)	0.015 (2)	0.011 (2)	−0.002 (2)
C30	0.055 (3)	0.069 (3)	0.046 (3)	0.019 (3)	0.024 (3)	0.004 (3)
C31	0.118 (6)	0.066 (4)	0.057 (4)	0.038 (4)	0.036 (4)	0.010 (3)

Geometric parameters (Å, º) top

Pt1A—Cl2	2.3281 (14)	C14—C15	1.526 (5)
Pt1A—N3	2.149 (4)	C15—H15A	0.9900
Pt1A—C13	2.091 (4)	C15—H15B	0.9900
Pt1A—C14	2.117 (4)	C15—C16	1.510 (5)
Pt1A—C21	2.003 (4)	C16—C17	1.395 (5)
Pt1B—Cl2	2.205 (6)	C16—C21	1.406 (5)
Pt1B—N3	2.330 (11)	C17—H17	0.9500
Pt1B—C13	2.45 (2)	C17—C18	1.383 (6)
Pt1B—C14	2.178 (9)	C18—C19	1.394 (6)
Pt1B—C21	1.965 (9)	C18—O22	1.382 (5)
N3—C4	1.316 (5)	C19—C20	1.386 (5)
N3—C12	1.354 (5)	C19—O24	1.395 (5)
C4—H4	0.9500	C20—H20	0.9500
C4—C5	1.400 (6)	C20—C21	1.400 (5)
C5—H5	0.9500	O22—C23	1.427 (5)
C5—C6	1.377 (6)	C23—H23A	0.9800
C6—H6	0.9500	C23—H23B	0.9800
C6—C7	1.415 (5)	C23—H23C	0.9800
C7—C8	1.412 (5)	O24—C25	1.425 (5)
C7—C12	1.414 (5)	C25—H25A	0.9900
C8—H8	0.9500	C25—H25B	0.9900
C8—C9	1.350 (6)	C25—C26	1.492 (6)
C9—H9	0.9500	C26—O27	1.197 (5)
C9—C10	1.404 (6)	C26—O28	1.344 (5)
C10—H10	0.9500	O28—C29	1.456 (5)
C10—C11	1.362 (5)	C29—H29A	0.9900
C11—H11	0.9500	C29—H29B	0.9900
C11—C12	1.424 (5)	C29—C30	1.496 (6)
C13—H13C	0.9900	C30—H30A	0.9900
C13—H13D	0.9900	C30—H30B	0.9900
C13—H13A	0.9900	C30—C31	1.524 (7)
C13—H13B	0.9900	C31—H31A	0.9800
C13—C14	1.392 (5)	C31—H31B	0.9800
C14—H14A	1.0000	C31—H31C	0.9800
C14—H14	1.0000

N3—Pt1A—Cl2	85.99 (10)	C13—C14—H14	114.9
C13—Pt1A—Cl2	161.77 (14)	C13—C14—C15	121.7 (4)
C13—Pt1A—N3	91.42 (16)	C15—C14—Pt1A	109.2 (3)
C13—Pt1A—C14	38.62 (14)	C15—C14—Pt1B	101.2 (5)
C14—Pt1A—Cl2	159.56 (15)	C15—C14—H14A	115.7
C14—Pt1A—N3	98.43 (15)	C15—C14—H14	114.9
C21—Pt1A—Cl2	94.43 (13)	C14—C15—H15A	109.7
C21—Pt1A—N3	178.23 (17)	C14—C15—H15B	109.7
C21—Pt1A—C13	87.65 (17)	H15A—C15—H15B	108.2
C21—Pt1A—C14	81.77 (16)	C16—C15—C14	109.7 (3)
Cl2—Pt1B—N3	84.7 (3)	C16—C15—H15A	109.7
Cl2—Pt1B—C13	139.1 (12)	C16—C15—H15B	109.7
N3—Pt1B—C13	78.8 (6)	C17—C16—C15	122.7 (4)
C14—Pt1B—Cl2	173.3 (14)	C17—C16—C21	121.3 (4)
C14—Pt1B—N3	91.5 (4)	C21—C16—C15	115.9 (4)
C14—Pt1B—C13	34.4 (3)	C16—C17—H17	119.8
C21—Pt1B—Cl2	99.5 (3)	C18—C17—C16	120.3 (4)
C21—Pt1B—N3	150.2 (15)	C18—C17—H17	119.8
C21—Pt1B—C13	79.0 (6)	C17—C18—C19	119.1 (4)
C21—Pt1B—C14	81.1 (4)	O22—C18—C17	125.0 (4)
C4—N3—Pt1A	116.6 (3)	O22—C18—C19	115.9 (4)
C4—N3—Pt1B	127.8 (7)	C18—C19—O24	120.2 (4)
C4—N3—C12	118.8 (4)	C20—C19—C18	120.7 (4)
C12—N3—Pt1A	123.8 (3)	C20—C19—O24	118.9 (4)
C12—N3—Pt1B	111.5 (7)	C19—C20—H20	119.4
N3—C4—H4	117.6	C19—C20—C21	121.2 (4)
N3—C4—C5	124.8 (4)	C21—C20—H20	119.4
C5—C4—H4	117.6	C16—C21—Pt1A	116.3 (3)
C4—C5—H5	121.4	C16—C21—Pt1B	113.2 (4)
C6—C5—C4	117.2 (4)	C20—C21—Pt1A	126.3 (3)
C6—C5—H5	121.4	C20—C21—Pt1B	127.8 (4)
C5—C6—H6	120.1	C20—C21—C16	117.3 (4)
C5—C6—C7	119.8 (4)	C18—O22—C23	117.9 (4)
C7—C6—H6	120.1	O22—C23—H23A	109.5
C8—C7—C6	122.3 (4)	O22—C23—H23B	109.5
C8—C7—C12	119.5 (4)	O22—C23—H23C	109.5
C12—C7—C6	118.2 (4)	H23A—C23—H23B	109.5
C7—C8—H8	119.3	H23A—C23—H23C	109.5
C9—C8—C7	121.4 (4)	H23B—C23—H23C	109.5
C9—C8—H8	119.3	C19—O24—C25	114.5 (3)
C8—C9—H9	120.6	O24—C25—H25A	109.2
C8—C9—C10	118.7 (4)	O24—C25—H25B	109.2
C10—C9—H9	120.6	O24—C25—C26	112.2 (4)
C9—C10—H10	118.6	H25A—C25—H25B	107.9
C11—C10—C9	122.8 (4)	C26—C25—H25A	109.2
C11—C10—H10	118.6	C26—C25—H25B	109.2
C10—C11—H11	120.5	O27—C26—C25	127.0 (5)
C10—C11—C12	119.0 (4)	O27—C26—O28	124.3 (5)
C12—C11—H11	120.5	O28—C26—C25	108.7 (4)
N3—C12—C7	121.1 (4)	C26—O28—C29	116.9 (4)
N3—C12—C11	120.3 (4)	O28—C29—H29A	110.3
C7—C12—C11	118.6 (4)	O28—C29—H29B	110.3
Pt1A—C13—H13C	116.4	O28—C29—C30	107.1 (4)
Pt1A—C13—H13D	116.4	H29A—C29—H29B	108.6
Pt1B—C13—H13A	117.6	C30—C29—H29A	110.3
Pt1B—C13—H13B	117.6	C30—C29—H29B	110.3
H13C—C13—H13D	113.4	C29—C30—H30A	109.3
H13A—C13—H13B	114.7	C29—C30—H30B	109.3
C14—C13—Pt1A	71.7 (3)	C29—C30—C31	111.5 (4)
C14—C13—Pt1B	62.0 (5)	H30A—C30—H30B	108.0
C14—C13—H13C	116.4	C31—C30—H30A	109.3
C14—C13—H13D	116.4	C31—C30—H30B	109.3
C14—C13—H13A	117.6	C30—C31—H31A	109.5
C14—C13—H13B	117.6	C30—C31—H31B	109.5
Pt1A—C14—H14A	115.7	C30—C31—H31C	109.5
Pt1B—C14—H14	114.9	H31A—C31—H31B	109.5
C13—C14—Pt1A	69.7 (2)	H31A—C31—H31C	109.5
C13—C14—Pt1B	83.7 (8)	H31B—C31—H31C	109.5
C13—C14—H14A	115.7

Pt1A—N3—C4—C5	167.9 (3)	C15—C16—C17—C18	174.9 (4)
Pt1A—N3—C12—C7	−168.1 (3)	C15—C16—C21—Pt1A	5.0 (5)
Pt1A—N3—C12—C11	11.9 (5)	C15—C16—C21—Pt1B	−11.5 (9)
Pt1A—C13—C14—C15	100.5 (4)	C15—C16—C21—C20	−177.8 (3)
Pt1A—C14—C15—C16	28.6 (4)	C16—C17—C18—C19	3.2 (6)
Pt1B—N3—C4—C5	160.7 (5)	C16—C17—C18—O22	−175.2 (4)
Pt1B—N3—C12—C7	−164.3 (4)	C17—C16—C21—Pt1A	−179.2 (3)
Pt1B—N3—C12—C11	15.7 (5)	C17—C16—C21—Pt1B	164.3 (9)
Pt1B—C13—C14—C15	99.3 (4)	C17—C16—C21—C20	−2.0 (6)
Pt1B—C14—C15—C16	40.6 (8)	C17—C18—C19—C20	−3.2 (6)
N3—C4—C5—C6	1.0 (7)	C17—C18—C19—O24	−177.7 (4)
C4—N3—C12—C7	1.1 (6)	C17—C18—O22—C23	−3.9 (6)
C4—N3—C12—C11	−178.9 (4)	C18—C19—C20—C21	0.5 (6)
C4—C5—C6—C7	1.1 (6)	C18—C19—O24—C25	−69.9 (5)
C5—C6—C7—C8	178.0 (4)	C19—C18—O22—C23	177.7 (4)
C5—C6—C7—C12	−2.0 (6)	C19—C20—C21—Pt1A	178.9 (3)
C6—C7—C8—C9	−179.1 (4)	C19—C20—C21—Pt1B	−162.0 (11)
C6—C7—C12—N3	0.9 (6)	C19—C20—C21—C16	2.0 (6)
C6—C7—C12—C11	−179.1 (4)	C19—O24—C25—C26	−86.2 (4)
C7—C8—C9—C10	−1.7 (7)	C20—C19—O24—C25	115.6 (4)
C8—C7—C12—N3	−179.1 (4)	C21—C16—C17—C18	−0.6 (6)
C8—C7—C12—C11	0.9 (6)	O22—C18—C19—C20	175.4 (4)
C8—C9—C10—C11	0.7 (7)	O22—C18—C19—O24	0.9 (6)
C9—C10—C11—C12	1.1 (7)	O24—C19—C20—C21	175.1 (3)
C10—C11—C12—N3	178.1 (4)	O24—C25—C26—O27	4.0 (7)
C10—C11—C12—C7	−1.8 (6)	O24—C25—C26—O28	−175.4 (3)
C12—N3—C4—C5	−2.1 (7)	C25—C26—O28—C29	179.3 (4)
C12—C7—C8—C9	0.9 (6)	C26—O28—C29—C30	−179.8 (4)
C13—C14—C15—C16	−48.9 (5)	O27—C26—O28—C29	−0.1 (7)
C14—C15—C16—C17	161.5 (4)	O28—C29—C30—C31	177.4 (4)
C14—C15—C16—C21	−22.8 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of ring C16–C21.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O27ⁱ	0.95	2.59	3.445 (5)	150
C23—H23C···Cl2ⁱⁱ	0.98	2.70	3.618 (6)	157
C29—H29B···O24ⁱⁱⁱ	0.99	2.50	3.381 (7)	148
C6—H6···Cg1^iv	0.95	2.73	3.269 (5)	117

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

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Synthesis and crystal structures of three organoplatinum(II) complexes bearing natural aryl­olefin and quinoline derivatives

Supporting information

Key indicators

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Synthesis and crystal structures of three organoplatinum(II) complexes bearing natural arylolefin and quinoline derivatives