Dichloridobis[3-(4-chloro-phen-yl)-2,N,N-trimethyl-2,3-di-hydro-1,2,4-oxa-diazole-5-amine-κN (4)]platinum(II)-4-chloro-benzaldehyde (1/1).

In the title 1:1 co-crystal, [PtCl2(C11H14ClN3O)2]·C7H5ClO, the coordination polyhedron of the Pt(II) atom is slightly distorted square-planar with the chloride and 2,3-di-hydro-1,2,4-oxa-diazole ligands mutually trans, as the Pt atom lies on an inversion center. The 4-chloro-benzaldehyde mol-ecules are statistically disordered about an inversion centre with equal occupancies for the two positions. The Pt(II) complex forms a three-dimensional structure through C-H⋯Cl and weaker C-H⋯O inter-actions with the 4-chloro-benzaldehyde mol-ecule.

Related literature

For the synthesis of platinum complexes with 2,3-di­hydro-1,2,4-oxa­diazole ligands, see: Bokach et al. (2011 ▶); Kritchenkov et al. (2011 ▶). For related structures, see: Bokach et al. (2003 ▶, 2011 ▶); Kritchenkov et al. (2011 ▶); Bokach & Kukushkin (2006 ▶); Gushchin et al. (2008 ▶); Kuznetsov & Kukushkin (2006 ▶); Fritsky et al. (2006 ▶); Penkova et al. (2009 ▶). For standard bond lengths, see: see: Allen et al. (1987 ▶).

Experimental

Crystal data

[PtCl2(C11H15ClN3O)2]·C7H5ClO

M = 887.97

Triclinic,

a = 8.46436 (18) Å

b = 9.38481 (19) Å

c = 11.4373 (3) Å

α = 101.0381 (18)°

β = 104.9553 (19)°

γ = 96.3847 (17)°

V = 849.07 (3) Å3

Z = 1

Mo Kα radiation

μ = 4.57 mm−1

T = 100 K

0.17 × 0.11 × 0.09 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.933, T max = 1.000

13908 measured reflections

3892 independent reflections

3888 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.054

S = 1.06

3892 reflections

211 parameters

H-atom parameters constrained

Δρmax = 1.63 e Å−3

Δρmin = −1.21 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813017376/sj5329sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017376/sj5329Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[PtCl2(C11H15ClN3O)2]·C7H5ClO	Z = 1
Mr = 887.97	F(000) = 438
Triclinic, P1	Dx = 1.737 Mg m−3
a = 8.46436 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.38481 (19) Å	Cell parameters from 9801 reflections
c = 11.4373 (3) Å	θ = 2.5–31.7°
α = 101.0381 (18)°	µ = 4.57 mm−1
β = 104.9553 (19)°	T = 100 K
γ = 96.3847 (17)°	Prism, colourless
V = 849.07 (3) Å3	0.17 × 0.11 × 0.09 mm

Agilent Xcalibur Eos diffractometer	3892 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3888 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 16.2096 pixels mm-1	θmax = 27.5°, θmin = 2.5°
ω scans	h = −10→10
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = −12→12
Tmin = 0.933, Tmax = 1.000	l = −14→14
13908 measured reflections

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.054	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0326P)2] where P = (Fo2 + 2Fc2)/3
3892 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 1.63 e Å−3
0 restraints	Δρmin = −1.21 e Å−3

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.

Refinement. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Pt1	0.5000	0.5000	0.0000	0.01562 (5)
O1	0.8747 (3)	0.5755 (3)	0.34126 (19)	0.0321 (5)
N2	0.9212 (3)	0.4486 (3)	0.2650 (2)	0.0290 (6)
H2	0.9972	0.4786	0.2273	0.035*
C3	0.7596 (4)	0.3810 (3)	0.1742 (3)	0.0243 (6)
H3	0.6936	0.3203	0.2112	0.029*
N4	0.6856 (3)	0.5130 (3)	0.1552 (2)	0.0209 (5)
C5	0.7499 (4)	0.6134 (3)	0.2577 (3)	0.0240 (6)
N6	0.7135 (3)	0.7450 (3)	0.2956 (2)	0.0281 (6)
C7	0.5711 (4)	0.8001 (4)	0.2268 (3)	0.0334 (7)
H7A	0.6050	0.8552	0.1723	0.050*
H7B	0.5293	0.8627	0.2843	0.050*
H7C	0.4856	0.7186	0.1788	0.050*
C8	0.8131 (5)	0.8425 (4)	0.4142 (3)	0.0451 (10)
H8A	0.7642	0.8272	0.4788	0.068*
H8B	0.8163	0.9432	0.4077	0.068*
H8C	0.9239	0.8209	0.4338	0.068*
C9	0.9849 (5)	0.3574 (4)	0.3496 (3)	0.0452 (10)
H9A	1.0813	0.4129	0.4134	0.068*
H9B	1.0142	0.2721	0.3045	0.068*
H9C	0.9012	0.3272	0.3869	0.068*
C10	0.7869 (4)	0.2884 (3)	0.0606 (3)	0.0230 (6)
C11	0.7575 (5)	0.1367 (4)	0.0400 (3)	0.0342 (7)
H11	0.7156	0.0919	0.0941	0.041*
C12	0.7907 (5)	0.0506 (4)	−0.0617 (3)	0.0434 (9)
H12	0.7705	−0.0516	−0.0765	0.052*
C13	0.8532 (5)	0.1191 (4)	−0.1391 (3)	0.0365 (8)
Cl14	0.89823 (18)	0.01398 (12)	−0.26699 (9)	0.0619 (3)
C15	0.8828 (4)	0.2708 (4)	−0.1219 (3)	0.0306 (7)
H15	0.9243	0.3150	−0.1764	0.037*
C16	0.8483 (4)	0.3547 (3)	−0.0206 (3)	0.0257 (6)
H16	0.8667	0.4569	−0.0070	0.031*
Cl17	0.34015 (9)	0.32493 (9)	0.05713 (7)	0.03003 (16)
C19	0.5885 (5)	0.4816 (5)	0.6159 (4)	0.0510 (11)
H19	0.6474	0.4686	0.6927	0.061*
C20	0.5665 (6)	0.3740 (5)	0.5084 (4)	0.0493 (11)
C18	0.4783 (5)	0.3921 (5)	0.3929 (4)	0.0479 (10)
H18	0.4643	0.3190	0.3217	0.057*
Cl21	0.6390 (5)	0.2036 (3)	0.5142 (4)	0.0640 (9)	0.50
C21	0.659 (3)	0.2527 (18)	0.522 (2)	0.081 (2)	0.50
H21	0.7255	0.2501	0.6005	0.097*	0.50
O2	0.6509 (12)	0.1563 (8)	0.4337 (7)	0.081 (2)	0.50

	U11	U22	U33	U12	U13	U23
Pt1	0.01892 (8)	0.01346 (8)	0.01130 (7)	0.00185 (5)	0.00020 (5)	0.00142 (5)
O1	0.0370 (12)	0.0334 (13)	0.0173 (10)	0.0180 (10)	−0.0050 (9)	−0.0037 (9)
N2	0.0311 (13)	0.0305 (15)	0.0193 (12)	0.0135 (11)	−0.0004 (10)	−0.0033 (10)
C3	0.0280 (14)	0.0236 (15)	0.0188 (13)	0.0079 (12)	0.0013 (11)	0.0045 (11)
N4	0.0246 (12)	0.0176 (12)	0.0159 (11)	0.0040 (9)	−0.0003 (9)	0.0011 (9)
C5	0.0251 (14)	0.0276 (16)	0.0151 (13)	0.0071 (12)	0.0000 (11)	0.0017 (11)
N6	0.0340 (14)	0.0236 (13)	0.0170 (11)	0.0097 (11)	−0.0048 (10)	−0.0049 (10)
C7	0.0394 (18)	0.0260 (17)	0.0250 (15)	0.0147 (14)	−0.0038 (13)	−0.0047 (13)
C8	0.045 (2)	0.040 (2)	0.0297 (17)	0.0138 (16)	−0.0096 (15)	−0.0164 (15)
C9	0.053 (2)	0.048 (2)	0.0264 (17)	0.0291 (19)	−0.0062 (16)	0.0022 (16)
C10	0.0247 (14)	0.0207 (15)	0.0178 (13)	0.0064 (11)	−0.0022 (11)	0.0006 (11)
C11	0.051 (2)	0.0262 (17)	0.0257 (15)	0.0055 (15)	0.0084 (15)	0.0094 (13)
C12	0.074 (3)	0.0135 (16)	0.0358 (18)	0.0094 (16)	0.0061 (18)	0.0007 (14)
C13	0.054 (2)	0.0323 (19)	0.0212 (15)	0.0222 (16)	0.0059 (15)	−0.0002 (13)
Cl14	0.1140 (10)	0.0441 (6)	0.0333 (5)	0.0409 (6)	0.0248 (6)	0.0019 (4)
C15	0.0342 (16)	0.0305 (17)	0.0308 (16)	0.0112 (13)	0.0120 (14)	0.0087 (13)
C16	0.0235 (14)	0.0187 (15)	0.0309 (15)	0.0017 (11)	0.0043 (12)	0.0022 (12)
Cl17	0.0284 (4)	0.0283 (4)	0.0350 (4)	0.0005 (3)	0.0072 (3)	0.0162 (3)
C19	0.067 (3)	0.069 (3)	0.037 (2)	0.037 (2)	0.027 (2)	0.028 (2)
C20	0.071 (3)	0.058 (3)	0.044 (2)	0.042 (2)	0.037 (2)	0.028 (2)
C18	0.067 (3)	0.058 (3)	0.0366 (19)	0.031 (2)	0.0315 (19)	0.0178 (18)
Cl21	0.100 (2)	0.059 (2)	0.0583 (16)	0.0507 (19)	0.0399 (15)	0.0301 (19)
C21	0.145 (7)	0.062 (5)	0.059 (4)	0.064 (5)	0.043 (4)	0.023 (4)
O2	0.145 (7)	0.062 (5)	0.059 (4)	0.064 (5)	0.043 (4)	0.023 (4)

Pt1—N4	2.018 (2)	C9—H9B	0.9600
Pt1—N4i	2.018 (2)	C9—H9C	0.9600
Pt1—Cl17	2.3087 (7)	C10—C11	1.381 (4)
Pt1—Cl17i	2.3087 (7)	C10—C16	1.385 (4)
O1—N2	1.490 (3)	C11—H11	0.9300
O1—C5	1.360 (3)	C11—C12	1.394 (5)
N2—H2	0.9100	C12—H12	0.9300
N2—C3	1.474 (4)	C12—C13	1.364 (5)
N2—C9	1.452 (4)	C13—Cl14	1.754 (3)
C3—H3	0.9800	C13—C15	1.385 (5)
C3—N4	1.476 (4)	C15—H15	0.9300
C3—C10	1.505 (4)	C15—C16	1.387 (4)
N4—C5	1.301 (4)	C16—H16	0.9300
C5—N6	1.325 (4)	C19—H19	0.9300
N6—C7	1.464 (4)	C19—C20	1.389 (6)
N6—C8	1.467 (4)	C19—C18ii	1.378 (6)
C7—H7A	0.9600	C20—C18	1.391 (5)
C7—H7B	0.9600	C20—Cl21	1.782 (5)
C7—H7C	0.9600	C20—C21	1.465 (18)
C8—H8A	0.9600	C18—C19ii	1.378 (6)
C8—H8B	0.9600	C18—H18	0.9300
C8—H8C	0.9600	C21—H21	0.9300
C9—H9A	0.9600	C21—O2	1.20 (2)
N4—Pt1—N4i	180.0	N2—C9—H9A	109.5
N4i—Pt1—Cl17	90.47 (7)	N2—C9—H9B	109.5
N4—Pt1—Cl17	89.53 (7)	N2—C9—H9C	109.5
N4i—Pt1—Cl17i	89.53 (7)	H9A—C9—H9B	109.5
N4—Pt1—Cl17i	90.47 (7)	H9A—C9—H9C	109.5
Cl17—Pt1—Cl17i	180.0	H9B—C9—H9C	109.5
C5—O1—N2	103.2 (2)	C11—C10—C3	119.9 (3)
O1—N2—H2	111.8	C11—C10—C16	119.8 (3)
C3—N2—O1	101.1 (2)	C16—C10—C3	120.2 (3)
C3—N2—H2	111.8	C10—C11—H11	119.9
C9—N2—O1	106.0 (2)	C10—C11—C12	120.1 (3)
C9—N2—H2	111.8	C12—C11—H11	119.9
C9—N2—C3	113.6 (3)	C11—C12—H12	120.6
N2—C3—H3	110.1	C13—C12—C11	118.8 (3)
N2—C3—N4	101.0 (2)	C13—C12—H12	120.6
N2—C3—C10	109.5 (2)	C12—C13—Cl14	119.9 (3)
N4—C3—H3	110.1	C12—C13—C15	122.6 (3)
N4—C3—C10	115.5 (2)	C15—C13—Cl14	117.5 (3)
C10—C3—H3	110.1	C13—C15—H15	121.1
C3—N4—Pt1	119.50 (17)	C13—C15—C16	117.8 (3)
C5—N4—Pt1	133.5 (2)	C16—C15—H15	121.1
C5—N4—C3	106.5 (2)	C10—C16—C15	120.9 (3)
N4—C5—O1	114.1 (3)	C10—C16—H16	119.6
N4—C5—N6	131.3 (3)	C15—C16—H16	119.6
N6—C5—O1	114.5 (2)	C20—C19—H19	120.4
C5—N6—C7	123.4 (2)	C18ii—C19—H19	120.4
C5—N6—C8	120.6 (3)	C18ii—C19—C20	119.1 (4)
C7—N6—C8	115.9 (3)	C19—C20—C18	121.0 (4)
N6—C7—H7A	109.5	C19—C20—Cl21	121.3 (3)
N6—C7—H7B	109.5	C19—C20—C21	116.0 (9)
N6—C7—H7C	109.5	C18—C20—Cl21	117.5 (4)
H7A—C7—H7B	109.5	C18—C20—C21	122.5 (9)
H7A—C7—H7C	109.5	C21—C20—Cl21	11.6 (10)
H7B—C7—H7C	109.5	C19ii—C18—C20	119.9 (4)
N6—C8—H8A	109.5	C19ii—C18—H18	120.1
N6—C8—H8B	109.5	C20—C18—H18	120.1
N6—C8—H8C	109.5	C20—C21—H21	119.7
H8A—C8—H8B	109.5	O2—C21—C20	120.5 (17)
H8A—C8—H8C	109.5	O2—C21—H21	119.7
H8B—C8—H8C	109.5
Pt1—N4—C5—O1	179.0 (2)	C9—N2—C3—C10	−88.6 (3)
Pt1—N4—C5—N6	0.1 (5)	C10—C3—N4—Pt1	41.0 (3)
O1—N2—C3—N4	36.0 (3)	C10—C3—N4—C5	−146.2 (3)
O1—N2—C3—C10	158.3 (2)	C10—C11—C12—C13	0.5 (5)
O1—C5—N6—C7	−172.6 (3)	C11—C10—C16—C15	−0.7 (4)
O1—C5—N6—C8	4.9 (5)	C11—C12—C13—Cl14	179.4 (3)
N2—O1—C5—N4	16.2 (3)	C11—C12—C13—C15	−1.1 (6)
N2—O1—C5—N6	−164.7 (3)	C12—C13—C15—C16	0.7 (5)
N2—C3—N4—Pt1	159.05 (18)	C13—C15—C16—C10	0.2 (5)
N2—C3—N4—C5	−28.1 (3)	Cl14—C13—C15—C16	−179.7 (2)
N2—C3—C10—C11	105.8 (3)	C16—C10—C11—C12	0.4 (5)
N2—C3—C10—C16	−71.3 (3)	Cl17—Pt1—N4—C3	61.0 (2)
C3—N4—C5—O1	7.6 (3)	Cl17i—Pt1—N4—C3	−119.0 (2)
C3—N4—C5—N6	−171.3 (3)	Cl17i—Pt1—N4—C5	70.5 (3)
C3—C10—C11—C12	−176.7 (3)	Cl17—Pt1—N4—C5	−109.5 (3)
C3—C10—C16—C15	176.4 (3)	C19—C20—C18—C19ii	0.1 (8)
N4i—Pt1—N4—C3	15 (24)	C19—C20—C21—O2	−178.3 (15)
N4i—Pt1—N4—C5	−155 (24)	C18ii—C19—C20—C18	−0.1 (7)
N4—C3—C10—C11	−141.0 (3)	C18ii—C19—C20—Cl21	−176.3 (4)
N4—C3—C10—C16	41.9 (4)	C18ii—C19—C20—C21	172.0 (11)
N4—C5—N6—C7	6.3 (6)	C18—C20—C21—O2	−6 (3)
N4—C5—N6—C8	−176.2 (4)	Cl21—C20—C18—C19ii	176.4 (4)
C5—O1—N2—C3	−32.6 (3)	Cl21—C20—C21—O2	61 (4)
C5—O1—N2—C9	−151.3 (3)	C21—C20—C18—C19ii	−171.4 (11)
C9—N2—C3—N4	149.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2iii	0.96	2.58	3.378 (9)	141
C12—H12···Cl17iv	0.93	2.70	3.589 (4)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2i	0.96	2.58	3.378 (9)	141
C12—H12⋯Cl17ii	0.93	2.70	3.589 (4)	160

Symmetry codes: (i) ; (ii) .