Literature DB >> 21589337

Diaqua-dichloridobis[quinazolin-4(1H)-one-κN]copper(II).

Kambarali Turgunov, Shirin Shomurotova, Nasir Mukhamedov, Bakhodir Tashkhodjaev.

Abstract

In the title complex, [CuCl(2)(C(8)H(n class="Chemical">6)N(2)O)(2)(H(2)O)(2)], the Cu(II) ion is located on an inversion center and is octahedrally coordinated by two N atoms of the 1H-quinazolin-4-one ligand, two chloride ligands and two aqua ligands. The axial Cu-O distances are significantly longer [2.512 (2) Å], than the Cu-N [2.022 (2) Å] and Cu-Cl [2.3232 (4) Å] distances as a result of Jahn-Teller distortion. Aqua ligands are involved in intra- and inter-molecular hydrogen bonding, and N-H⋯O inter-molecular hydrogen bonds are formed between the organic ligands. In addition, weak π-π inter-actions are observed between the benzene rings of the ligand [centroid-centroid distance = 3.678 (1) Å].

Entities: Chemical Disease Species

Year: 2010 PMID： 21589337 PMCID： PMC3011606 DOI： 10.1107/S1600536810048890

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

The crystal structure of pyrimidin-4(3H)-one was reported by Vaillancourt et al. (1998 ▶). For a Cd(II) coordination polymer with quinazolin-4(3H)-one, see: Turgunov & Englert (2010 ▶). For computational studies of quinazolin-4-one derivatives, see: Bakalova et al. (2004 ▶).

Experimental

Crystal data

[CuCl2(C8H6N2O)2(H2O)2] M = 462.77 Monoclinic, a = 6.7438 (3) Å b = 18.5328 (8) Å c = 6.7831 (3) Å β = 90.735 (3)° V = 847.69 (6) Å3 Z = 2 Cu Kα radiation μ = 5.03 mm−1 T = 293 K 0.55 × 0.35 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.366, T max = 1.000 5548 measured reflections 1725 independent reflections 1639 reflections with I > 2σ(I) R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.032 wR(F 2) = 0.089 S = 1.10 1725 reflections 137 parameters 3 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.37 e Å−3 Δρmin = −0.46 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Bruker, 1998 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810048890/nk2075sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048890/nk2075Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[CuCl₂(C₈H₆N₂O)₂(H₂O)₂]	F(000) = 470
M_r = 462.77	D_x = 1.813 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 4533 reflections
a = 6.7438 (3) Å	θ = 4.8–75.3°
b = 18.5328 (8) Å	µ = 5.03 mm⁻¹
c = 6.7831 (3) Å	T = 293 K
β = 90.735 (3)°	Prism, light-blue
V = 847.69 (6) Å³	0.55 × 0.35 × 0.20 mm
Z = 2

Oxford Diffraction Xcalibur Ruby diffractometer	1725 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1639 reflections with I > 2σ(I)
graphite	R_int = 0.040
Detector resolution: 10.2576 pixels mm^-1	θ_max = 77.1°, θ_min = 4.8°
ω scans	h = −5→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −23→22
T_min = 0.366, T_max = 1.000	l = −8→8
5548 measured reflections

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.089	w = 1/[σ²(F_o²) + (0.0535P)² + 0.3464P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
1725 reflections	Δρ_max = 0.37 e Å⁻³
137 parameters	Δρ_min = −0.46 e Å⁻³
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0067 (7)

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.

	x	y	z	U_iso*/U_eq
Cu1	0.0000	0.5000	0.5000	0.02135 (17)
Cl1	0.20934 (7)	0.45671 (2)	0.74764 (6)	0.02750 (17)
O1	−0.12427 (19)	0.66628 (7)	0.5870 (2)	0.0280 (3)
N1	0.4508 (2)	0.65113 (9)	0.4461 (2)	0.0227 (3)
C2	0.3358 (3)	0.59405 (10)	0.4636 (3)	0.0229 (4)
H2A	0.3936	0.5490	0.4458	0.028*
N3	0.1427 (2)	0.59595 (8)	0.5049 (2)	0.0209 (3)
C4	0.0522 (3)	0.66252 (9)	0.5382 (3)	0.0198 (4)
C4A	0.1738 (3)	0.72721 (10)	0.5123 (2)	0.0196 (4)
C5	0.0922 (3)	0.79617 (10)	0.5345 (3)	0.0239 (4)
H5A	−0.0399	0.8014	0.5693	0.029*
C6	0.2088 (3)	0.85635 (11)	0.5046 (3)	0.0288 (4)
H6A	0.1540	0.9022	0.5167	0.035*
C7	0.4101 (3)	0.84875 (11)	0.4560 (3)	0.0311 (4)
H7A	0.4871	0.8897	0.4363	0.037*
C8	0.4945 (3)	0.78128 (11)	0.4373 (3)	0.0276 (4)
H8A	0.6278	0.7764	0.4064	0.033*
C8A	0.3762 (3)	0.72057 (10)	0.4656 (2)	0.0205 (4)
O1W	0.2398 (3)	0.46004 (9)	0.2416 (2)	0.0356 (4)
H1W	0.218 (5)	0.4172 (11)	0.274 (5)	0.057 (10)*
H1	0.570 (3)	0.6432 (17)	0.417 (5)	0.054 (9)*
H2W	0.219 (6)	0.462 (2)	0.118 (3)	0.065 (10)*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0191 (2)	0.0140 (2)	0.0308 (3)	−0.00062 (12)	−0.00334 (16)	0.00158 (13)
Cl1	0.0262 (3)	0.0276 (3)	0.0286 (3)	0.00254 (16)	−0.00262 (18)	0.00244 (16)
O1	0.0175 (6)	0.0225 (7)	0.0441 (8)	0.0005 (5)	0.0050 (5)	−0.0008 (6)
N1	0.0149 (7)	0.0243 (8)	0.0290 (8)	0.0010 (6)	0.0006 (6)	0.0016 (6)
C2	0.0209 (8)	0.0190 (8)	0.0289 (9)	0.0025 (7)	−0.0013 (7)	0.0001 (7)
N3	0.0189 (7)	0.0161 (7)	0.0278 (7)	0.0015 (5)	−0.0009 (6)	0.0013 (6)
C4	0.0198 (8)	0.0170 (8)	0.0224 (8)	−0.0001 (6)	−0.0017 (6)	−0.0003 (6)
C4A	0.0196 (8)	0.0200 (8)	0.0191 (7)	−0.0005 (6)	−0.0020 (6)	−0.0002 (6)
C5	0.0256 (9)	0.0208 (9)	0.0253 (9)	0.0006 (7)	−0.0017 (7)	−0.0013 (7)
C6	0.0395 (11)	0.0180 (9)	0.0287 (9)	−0.0010 (8)	−0.0041 (8)	−0.0005 (7)
C7	0.0387 (11)	0.0230 (10)	0.0315 (10)	−0.0141 (8)	−0.0021 (8)	0.0013 (7)
C8	0.0242 (9)	0.0306 (10)	0.0280 (9)	−0.0088 (8)	−0.0003 (7)	0.0016 (8)
C8A	0.0205 (8)	0.0218 (9)	0.0192 (7)	−0.0024 (7)	−0.0027 (6)	0.0006 (6)
O1W	0.0416 (9)	0.0273 (8)	0.0380 (9)	0.0003 (6)	0.0032 (7)	−0.0016 (6)

Cu1—N3	2.0221 (15)	C4A—C5	1.400 (3)
Cu1—N3ⁱ	2.0221 (15)	C4A—C8A	1.410 (3)
Cu1—Cl1	2.3232 (4)	C5—C6	1.381 (3)
Cu1—Cl1ⁱ	2.3232 (4)	C5—H5A	0.9300
O1—C4	1.241 (2)	C6—C7	1.409 (3)
N1—C2	1.318 (2)	C6—H6A	0.9300
N1—C8A	1.389 (2)	C7—C8	1.380 (3)
N1—H1	0.841 (18)	C7—H7A	0.9300
C2—N3	1.336 (2)	C8—C8A	1.394 (3)
C2—H2A	0.9300	C8—H8A	0.9300
N3—C4	1.396 (2)	O1W—H1W	0.837 (18)
C4—C4A	1.464 (2)	O1W—H2W	0.848 (19)

N3—Cu1—N3ⁱ	180.0	C5—C4A—C4	120.84 (16)
N3—Cu1—Cl1	90.40 (4)	C8A—C4A—C4	120.04 (16)
N3ⁱ—Cu1—Cl1	89.60 (4)	C6—C5—C4A	119.75 (18)
N3—Cu1—Cl1ⁱ	89.60 (4)	C6—C5—H5A	120.1
N3ⁱ—Cu1—Cl1ⁱ	90.40 (4)	C4A—C5—H5A	120.1
Cl1—Cu1—Cl1ⁱ	180.0	C5—C6—C7	120.38 (19)
C2—N1—C8A	121.43 (15)	C5—C6—H6A	119.8
C2—N1—H1	116 (2)	C7—C6—H6A	119.8
C8A—N1—H1	122 (2)	C8—C7—C6	120.79 (17)
N1—C2—N3	125.02 (16)	C8—C7—H7A	119.6
N1—C2—H2A	117.5	C6—C7—H7A	119.6
N3—C2—H2A	117.5	C7—C8—C8A	118.77 (18)
C2—N3—C4	119.11 (15)	C7—C8—H8A	120.6
C2—N3—Cu1	116.00 (12)	C8A—C8—H8A	120.6
C4—N3—Cu1	124.80 (12)	N1—C8A—C8	121.77 (17)
O1—C4—N3	121.02 (16)	N1—C8A—C4A	117.05 (15)
O1—C4—C4A	121.77 (16)	C8—C8A—C4A	121.17 (17)
N3—C4—C4A	117.21 (15)	H1W—O1W—H2W	106 (3)
C5—C4A—C8A	119.11 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O1ⁱ	0.84 (2)	1.92 (3)	2.732 (2)	162 (3)
O1W—H2W···Cl1ⁱⁱ	0.85 (2)	2.51 (2)	3.355 (2)	171 (4)
N1—H1···O1ⁱⁱⁱ	0.84 (2)	2.39 (3)	3.022 (2)	133 (3)
N1—H1···Cl1^iv	0.84 (2)	2.63 (3)	3.324 (2)	140 (3)
C2—H2A···O1W	0.93	2.38	2.972 (3)	121
C7—H7A···O1W^v	0.93	2.57	3.421 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O1ⁱ	0.84 (2)	1.92 (3)	2.732 (2)	162 (3)
O1W—H2W⋯Cl1ⁱⁱ	0.85 (2)	2.51 (2)	3.355 (2)	171 (4)
N1—H1⋯O1ⁱⁱⁱ	0.84 (2)	2.39 (3)	3.022 (2)	133 (3)
N1—H1⋯Cl1^iv	0.84 (2)	2.63 (3)	3.324 (2)	140 (3)
C2—H2A⋯O1W	0.93	2.38	2.972 (3)	121
C7—H7A⋯O1W^v	0.93	2.57	3.421 (3)	152

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. catena-Poly[[bis[quinazolin-4(3H)-one-κN]cadmium(II)]-di-μ-chlorido].

Authors: Kambarali Turgunov; Ulli Englert
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-10-23

2 in total

1 in total

1. Diaqua-dichloridobis[quinazolin-4(1H)-one-κN(3)]nickel(II).

Authors: Shirin Shomurotova; Kambarali K Turgunov; Nasir Mukhamedov; Bakhodir Tashkhodjaev
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-05-05

1 in total