Crystal structure of chlorido­(piperidine-κN)(quinoline-2-carboxyl­ato-κ²N,O)platinum(II)

The platinum(II) complex with notable antitumor activity shows a slightly distorted square-planar coordination and intramolecular C—H...Cl and intermolecular N—H...Cl and C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.015
• wR factor = 0.035
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Why ?
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large.       9.14 Why ?
PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) .....          3 Why ?

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Chlorido(piperidine-kN)(quinoline-2-carboxylato-κ²N,O)platinum(II)

Crystal data

[Pt(C10H6NO2)Cl(C5H11N)]	F(000) = 1856
Mr = 487.85	Dx = 2.093 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.7107 Å
a = 22.7542 (8) Å	Cell parameters from 16449 reflections
b = 9.7540 (3) Å	θ = 3.4–29.8°
c = 14.0139 (5) Å	µ = 9.24 mm^−1
β = 95.542 (3)°	T = 200 K
V = 3095.78 (19) Å^3	Block, yellow
Z = 8	0.3 × 0.3 × 0.2 mm

Data collection

Agilent SuperNova (single source at offset, Eos detector) diffractometer	3166 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2951 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.026
Detector resolution: 15.9631 pixels mm^-1	θmax = 26.4°, θmin = 2.8°
ω scans	h = −28→28
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −12→12
Tmin = 0.473, Tmax = 1.000	l = −17→17
31419 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.015	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.035	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0118P)^2 + 9.138P] where P = (Fo^2 + 2Fc^2)/3
3166 reflections	(Δ/σ)max = 0.002
190 parameters	Δρmax = 0.80 e Å^−3
0 restraints	Δρmin = −0.53 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1	0.29348 (12)	0.6098 (3)	0.5028 (2)	0.0268 (6)
C2	0.25609 (13)	0.5746 (3)	0.4211 (2)	0.0327 (7)
H2	0.2227	0.5176	0.4264	0.039*
C3	0.26831 (14)	0.6232 (3)	0.3338 (2)	0.0354 (7)
H3	0.2432	0.6014	0.2777	0.042*
C4	0.31811 (14)	0.7052 (3)	0.3278 (2)	0.0324 (7)
C5	0.33360 (18)	0.7554 (4)	0.2386 (2)	0.0432 (8)
H5	0.3085	0.7372	0.1818	0.052*
C6	0.38367 (19)	0.8290 (4)	0.2332 (2)	0.0516 (10)
H6	0.3934	0.8625	0.1730	0.062*
C7	0.42105 (18)	0.8556 (4)	0.3167 (2)	0.0503 (9)
H7	0.4565	0.9057	0.3121	0.060*
C8	0.40769 (16)	0.8111 (3)	0.4047 (2)	0.0400 (8)
H8	0.4336	0.8309	0.4603	0.048*
C9	0.35561 (14)	0.7362 (3)	0.4130 (2)	0.0285 (6)
C10	0.28109 (13)	0.5514 (3)	0.5984 (2)	0.0318 (7)
C11	0.42217 (15)	0.5840 (3)	0.8206 (2)	0.0402 (8)
H11A	0.4518	0.5401	0.7832	0.048*
H11B	0.3857	0.5281	0.8125	0.048*
C12	0.44551 (16)	0.5867 (4)	0.9262 (3)	0.0479 (9)
H12A	0.4509	0.4914	0.9499	0.058*
H12B	0.4845	0.6323	0.9333	0.058*
C13	0.40413 (18)	0.6613 (5)	0.9861 (2)	0.0550 (10)
H13A	0.4225	0.6690	1.0528	0.066*
H13B	0.3671	0.6083	0.9869	0.066*
C14	0.39015 (16)	0.8039 (4)	0.9459 (2)	0.0443 (9)
H14A	0.4263	0.8607	0.9527	0.053*
H14B	0.3604	0.8481	0.9828	0.053*
C15	0.36650 (13)	0.7956 (3)	0.8404 (2)	0.0337 (7)
H15A	0.3285	0.7455	0.8344	0.040*
H15B	0.3591	0.8893	0.8150	0.040*
Cl1	0.45271 (3)	0.88368 (8)	0.62745 (5)	0.03279 (16)
N1	0.34113 (10)	0.6894 (2)	0.50082 (16)	0.0255 (5)
N2	0.40915 (10)	0.7240 (2)	0.78242 (16)	0.0264 (5)
H2A	0.4443	0.7733	0.7893	0.032*
O1	0.31888 (9)	0.5856 (2)	0.66939 (14)	0.0369 (5)
O2	0.23904 (10)	0.4760 (3)	0.60452 (16)	0.0433 (6)
Pt1	0.380802 (4)	0.720087 (11)	0.639573 (7)	0.02386 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0264 (14)	0.0266 (14)	0.0271 (14)	0.0071 (12)	0.0005 (11)	−0.0021 (12)
C2	0.0288 (15)	0.0374 (17)	0.0308 (15)	0.0016 (13)	−0.0034 (12)	−0.0040 (13)
C3	0.0374 (16)	0.0387 (18)	0.0281 (15)	0.0067 (14)	−0.0071 (12)	−0.0063 (13)
C4	0.0425 (17)	0.0282 (16)	0.0256 (15)	0.0079 (13)	−0.0006 (12)	−0.0035 (12)
C5	0.067 (2)	0.0370 (18)	0.0247 (16)	−0.0022 (17)	−0.0017 (15)	−0.0011 (13)
C6	0.086 (3)	0.042 (2)	0.0269 (16)	−0.014 (2)	0.0094 (17)	0.0007 (15)
C7	0.071 (3)	0.046 (2)	0.0345 (18)	−0.0231 (19)	0.0125 (17)	−0.0054 (16)
C8	0.052 (2)	0.0383 (18)	0.0298 (16)	−0.0106 (15)	0.0033 (14)	−0.0039 (13)
C9	0.0397 (16)	0.0213 (14)	0.0242 (14)	0.0045 (12)	0.0010 (12)	−0.0031 (11)
C10	0.0282 (15)	0.0393 (17)	0.0268 (14)	0.0012 (13)	−0.0028 (12)	−0.0017 (13)
C11	0.0421 (18)	0.0303 (17)	0.0443 (19)	0.0005 (14)	−0.0153 (15)	0.0051 (14)
C12	0.051 (2)	0.040 (2)	0.048 (2)	−0.0110 (16)	−0.0235 (17)	0.0172 (16)
C13	0.060 (2)	0.072 (3)	0.0299 (17)	−0.024 (2)	−0.0086 (16)	0.0155 (18)
C14	0.0404 (18)	0.065 (3)	0.0262 (16)	−0.0016 (17)	−0.0010 (13)	−0.0030 (15)
C15	0.0296 (15)	0.0433 (19)	0.0275 (15)	0.0027 (13)	−0.0014 (12)	0.0001 (13)
Cl1	0.0348 (4)	0.0335 (4)	0.0292 (3)	−0.0071 (3)	−0.0013 (3)	−0.0006 (3)
N1	0.0274 (12)	0.0244 (12)	0.0241 (11)	0.0033 (9)	−0.0002 (9)	−0.0026 (9)
N2	0.0240 (11)	0.0299 (13)	0.0242 (12)	−0.0014 (10)	−0.0028 (9)	0.0022 (10)
O1	0.0349 (11)	0.0493 (14)	0.0251 (10)	−0.0115 (10)	−0.0044 (9)	0.0061 (10)
O2	0.0350 (12)	0.0585 (16)	0.0350 (12)	−0.0179 (11)	−0.0031 (9)	0.0032 (11)
Pt1	0.02348 (6)	0.02556 (6)	0.02184 (6)	0.00129 (4)	−0.00148 (4)	−0.00049 (4)

Geometric parameters (Å, º)

C1—C2	1.402 (4)	C11—H11B	0.9900
C1—C10	1.507 (4)	C11—C12	1.524 (4)
C1—N1	1.336 (4)	C11—N2	1.486 (4)
C2—H2	0.9500	C12—H12A	0.9900
C2—C3	1.365 (4)	C12—H12B	0.9900
C3—H3	0.9500	C12—C13	1.507 (6)
C3—C4	1.396 (5)	C13—H13A	0.9900
C4—C5	1.419 (4)	C13—H13B	0.9900
C4—C9	1.432 (4)	C13—C14	1.522 (5)
C5—H5	0.9500	C14—H14A	0.9900
C5—C6	1.355 (5)	C14—H14B	0.9900
C6—H6	0.9500	C14—C15	1.526 (4)
C6—C7	1.403 (5)	C15—H15A	0.9900
C7—H7	0.9500	C15—H15B	0.9900
C7—C8	1.369 (5)	C15—N2	1.497 (4)
C8—H8	0.9500	Cl1—Pt1	2.3035 (7)
C8—C9	1.407 (5)	N1—Pt1	2.085 (2)
C9—N1	1.382 (4)	N2—H2A	0.9300
C10—O1	1.295 (3)	N2—Pt1	2.043 (2)
C10—O2	1.217 (4)	O1—Pt1	1.999 (2)
C11—H11A	0.9900
C2—C1—C10	118.8 (3)	H12A—C12—H12B	107.9
N1—C1—C2	123.8 (3)	C13—C12—C11	111.8 (3)
N1—C1—C10	117.4 (2)	C13—C12—H12A	109.3
C1—C2—H2	120.4	C13—C12—H12B	109.3
C3—C2—C1	119.1 (3)	C12—C13—H13A	109.5
C3—C2—H2	120.4	C12—C13—H13B	109.5
C2—C3—H3	120.3	C12—C13—C14	110.8 (3)
C2—C3—C4	119.3 (3)	H13A—C13—H13B	108.1
C4—C3—H3	120.3	C14—C13—H13A	109.5
C3—C4—C5	121.6 (3)	C14—C13—H13B	109.5
C3—C4—C9	119.5 (3)	C13—C14—H14A	109.5
C5—C4—C9	118.9 (3)	C13—C14—H14B	109.5
C4—C5—H5	119.5	C13—C14—C15	110.6 (3)
C6—C5—C4	120.9 (3)	H14A—C14—H14B	108.1
C6—C5—H5	119.5	C15—C14—H14A	109.5
C5—C6—H6	120.1	C15—C14—H14B	109.5
C5—C6—C7	119.8 (3)	C14—C15—H15A	109.4
C7—C6—H6	120.1	C14—C15—H15B	109.4
C6—C7—H7	119.2	H15A—C15—H15B	108.0
C8—C7—C6	121.6 (3)	N2—C15—C14	111.4 (3)
C8—C7—H7	119.2	N2—C15—H15A	109.4
C7—C8—H8	120.0	N2—C15—H15B	109.4
C7—C8—C9	120.1 (3)	C1—N1—C9	118.3 (2)
C9—C8—H8	120.0	C1—N1—Pt1	110.10 (18)
C8—C9—C4	118.7 (3)	C9—N1—Pt1	131.61 (19)
N1—C9—C4	119.9 (3)	C11—N2—C15	110.5 (2)
N1—C9—C8	121.4 (3)	C11—N2—H2A	107.4
O1—C10—C1	114.8 (3)	C11—N2—Pt1	111.61 (18)
O2—C10—C1	120.5 (3)	C15—N2—H2A	107.4
O2—C10—O1	124.7 (3)	C15—N2—Pt1	112.37 (17)
H11A—C11—H11B	107.9	Pt1—N2—H2A	107.4
C12—C11—H11A	109.2	C10—O1—Pt1	115.95 (19)
C12—C11—H11B	109.2	N1—Pt1—Cl1	106.11 (7)
N2—C11—H11A	109.2	N2—Pt1—Cl1	84.26 (7)
N2—C11—H11B	109.2	N2—Pt1—N1	169.63 (9)
N2—C11—C12	111.9 (3)	O1—Pt1—Cl1	171.99 (6)
C11—C12—H12A	109.3	O1—Pt1—N1	81.38 (9)
C11—C12—H12B	109.3	O1—Pt1—N2	88.26 (9)
C1—C2—C3—C4	0.8 (5)	C9—N1—Pt1—Cl1	8.2 (3)
C1—C10—O1—Pt1	5.1 (3)	C9—N1—Pt1—N2	−171.6 (4)
C1—N1—Pt1—Cl1	−171.51 (17)	C9—N1—Pt1—O1	−174.7 (3)
C1—N1—Pt1—N2	8.6 (6)	C10—C1—C2—C3	−177.6 (3)
C1—N1—Pt1—O1	5.58 (18)	C10—C1—N1—C9	175.6 (2)
C2—C1—C10—O1	177.8 (3)	C10—C1—N1—Pt1	−4.7 (3)
C2—C1—C10—O2	−0.7 (4)	C10—O1—Pt1—N1	−6.0 (2)
C2—C1—N1—C9	−2.1 (4)	C10—O1—Pt1—N2	174.6 (2)
C2—C1—N1—Pt1	177.6 (2)	C11—C12—C13—C14	−53.6 (4)
C2—C3—C4—C5	178.4 (3)	C11—N2—Pt1—Cl1	−129.0 (2)
C2—C3—C4—C9	0.4 (4)	C11—N2—Pt1—N1	50.9 (6)
C3—C4—C5—C6	−176.6 (3)	C11—N2—Pt1—O1	53.9 (2)
C3—C4—C9—C8	175.7 (3)	C12—C11—N2—C15	−56.3 (3)
C3—C4—C9—N1	−2.5 (4)	C12—C11—N2—Pt1	177.9 (2)
C4—C5—C6—C7	0.3 (6)	C12—C13—C14—C15	54.5 (4)
C4—C9—N1—C1	3.3 (4)	C13—C14—C15—N2	−56.9 (4)
C4—C9—N1—Pt1	−176.4 (2)	C14—C15—N2—C11	57.6 (3)
C5—C4—C9—C8	−2.3 (4)	C14—C15—N2—Pt1	−177.0 (2)
C5—C4—C9—N1	179.4 (3)	C15—N2—Pt1—Cl1	106.25 (19)
C5—C6—C7—C8	−1.3 (6)	C15—N2—Pt1—N1	−73.9 (6)
C6—C7—C8—C9	0.3 (6)	C15—N2—Pt1—O1	−70.9 (2)
C7—C8—C9—C4	1.5 (5)	N1—C1—C2—C3	0.0 (5)
C7—C8—C9—N1	179.7 (3)	N1—C1—C10—O1	0.0 (4)
C8—C9—N1—C1	−174.9 (3)	N1—C1—C10—O2	−178.5 (3)
C8—C9—N1—Pt1	5.4 (4)	N2—C11—C12—C13	54.9 (4)
C9—C4—C5—C6	1.4 (5)	O2—C10—O1—Pt1	−176.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1^i	0.93	2.74	3.624 (2)	160
C3—H3···O2^ii	0.96	2.53	3.360 (4)	145
C8—H8···Cl1	0.95	2.40	3.268 (3)	152

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