Diaqua-bis(3,7-dichloro-quinoline-8-carboxyl-ato)zinc(II) monohydrate.

In the title compound, [Zn(C(10)H(4)Cl(2)NO(2))(2)(H(2)O)(2)]·H(2)O, the Zn atom has a distorted square-pyramidal geometry comprising two O atoms and one N atom from two distinct 3,7-dichloro-quinoline-8-carboxyl-ate ligands, and two water mol-ecules. The free water mol-ecules are involved in inter-molecular O-H⋯O hydrogen bonding with the coordinated water mol-ecules and carboxyl-ate O atoms, to give a one-dimensional helical chain along the [100] direction.

Related literature

For related literature, see: Adnan et al. (2003 ▶); Che et al. (2005 ▶); Chen et al. (2001 ▶); Li et al. (2008 ▶); Lumme et al. (1984 ▶); Yang et al. (2005 ▶); Zhang et al. (2007 ▶).

Experimental

Crystal data

[Zn(C10H4Cl2NO2)2(H2O)2]·n class="Chemical">H2O

M = 601.50

Triclinic,

a = 6.8678 (3) Å

b = 12.6996 (5) Å

c = 12.9317 (5) Å

α = 87.572 (1)°

β = 82.893 (1)°

γ = 82.255 (1)°

V = 1108.63 (8) Å3

Z = 2

Mo Kα radiation

μ = 1.64 mm−1

T = 296 (2) K

0.21 × 0.17 × 0.15 mm

Data collection

Rigaku Mercury diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2001 ▶) T min = 0.725, T max = 0.791

14022 measured reflections

4308 independent reflections

3099 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.094

S = 0.97

4308 reflections

307 parameters

H-atom parameters constrained

Δρmax = 1.20 e Å−3

Δρmin = −0.80 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025671/sg2255sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025671/sg2255Isup2.hkl

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

[Zn(C10H4Cl2NO2)2(H2O)2]·H2O	Z = 2
Mr = 601.50	F000 = 604
Triclinic, P1	Dx = 1.802 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.8678 (3) Å	Cell parameters from 1973 reflections
b = 12.6996 (5) Å	θ = 1.6–26.0º
c = 12.9317 (5) Å	µ = 1.64 mm−1
α = 87.572 (1)º	T = 296 (2) K
β = 82.893 (1)º	Column, colourless
γ = 82.255 (1)º	0.21 × 0.17 × 0.15 mm
V = 1108.63 (8) Å3

Rigaku Mercury diffractometer	4308 independent reflections
Radiation source: fine-focus sealed tube	3099 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.080
Detector resolution: 7.31 pixels mm-1	θmax = 26.0º
T = 296(2) K	θmin = 1.6º
ω scans	h = −8→8
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2001)	k = −15→15
Tmin = 0.725, Tmax = 0.791	l = −15→14
14022 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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0408P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max = 0.001
4308 reflections	Δρmax = 1.20 e Å−3
307 parameters	Δρmin = −0.80 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	Uiso*/Ueq
C1	0.2965 (5)	0.6256 (3)	0.2794 (3)	0.0197 (8)
H1	0.3070	0.6713	0.2215	0.024*
C2	0.3295 (5)	0.5161 (3)	0.2636 (3)	0.0194 (8)
C3	0.3176 (5)	0.4475 (3)	0.3464 (3)	0.0209 (8)
H3	0.3380	0.3746	0.3366	0.025*
C4	0.2565 (5)	0.4215 (3)	0.5377 (3)	0.0210 (8)
H4	0.2778	0.3480	0.5315	0.025*
C5	0.2088 (5)	0.4641 (3)	0.6336 (3)	0.0241 (9)
H5	0.1921	0.4201	0.6925	0.029*
C6	0.1848 (5)	0.5751 (3)	0.6434 (3)	0.0186 (8)
C7	0.2042 (5)	0.6439 (3)	0.5590 (3)	0.0176 (8)
C8	0.2434 (5)	0.5998 (3)	0.4583 (3)	0.0173 (8)
C9	0.2741 (5)	0.4879 (3)	0.4474 (3)	0.0188 (8)
C10	0.2017 (6)	0.7613 (3)	0.5715 (3)	0.0220 (8)
C11	−0.2472 (5)	1.1168 (3)	0.1346 (3)	0.0194 (8)
H11	−0.2486	1.1675	0.1846	0.023*
C12	−0.2620 (5)	1.1520 (3)	0.0307 (3)	0.0182 (8)
C13	−0.2648 (5)	1.0809 (3)	−0.0443 (3)	0.0179 (8)
H13	−0.2756	1.1034	−0.1129	0.022*
C14	−0.2534 (5)	0.8915 (3)	−0.0880 (3)	0.0221 (8)
H14	−0.2643	0.9098	−0.1577	0.027*
C15	−0.2399 (5)	0.7872 (3)	−0.0559 (3)	0.0213 (8)
H15	−0.2427	0.7346	−0.1034	0.026*
C16	−0.2218 (5)	0.7597 (3)	0.0488 (3)	0.0196 (8)
C17	−0.2162 (5)	0.8341 (3)	0.1213 (3)	0.0167 (8)
C18	−0.2329 (5)	0.9426 (3)	0.0898 (3)	0.0170 (8)
C19	−0.2509 (5)	0.9721 (3)	−0.0157 (3)	0.0172 (8)
C20	−0.1707 (5)	0.8066 (3)	0.2315 (3)	0.0179 (8)
Cl1	0.37704 (15)	0.47230 (7)	0.13739 (7)	0.0300 (2)
Cl2	0.12831 (15)	0.62268 (8)	0.76860 (7)	0.0300 (2)
Cl3	−0.28261 (14)	1.28675 (7)	0.00156 (7)	0.0247 (2)
Cl4	−0.19519 (15)	0.62565 (7)	0.08517 (8)	0.0295 (2)
N1	0.2514 (4)	0.6674 (2)	0.3722 (2)	0.0185 (7)
N2	−0.2316 (4)	1.0165 (2)	0.1644 (2)	0.0190 (7)
O1	0.0705 (4)	0.82485 (19)	0.52664 (19)	0.0294 (7)
O2	0.3222 (4)	0.7909 (2)	0.6231 (2)	0.0325 (7)
O3	0.0098 (3)	0.80624 (19)	0.24133 (19)	0.0222 (6)
O4	−0.3021 (4)	0.78885 (19)	0.3020 (2)	0.0289 (6)
O5	−0.0852 (4)	0.9774 (2)	0.3738 (2)	0.0336 (7)
H5A	−0.0800	1.0295	0.4126	0.040*
H5B	−0.1398	0.9842	0.3175	0.040*
O6	0.3458 (4)	0.9015 (2)	0.3214 (2)	0.0350 (7)
H6A	0.4589	0.8647	0.3195	0.042*
H6B	0.3090	0.9657	0.3391	0.042*
O7	0.3413 (5)	0.1059 (3)	0.3655 (3)	0.0858 (14)
H7B	0.4519	0.1189	0.3815	0.103*
H7C	0.2491	0.1273	0.4129	0.103*
Zn1	0.10699 (6)	0.83389 (3)	0.37255 (3)	0.01835 (13)

	U11	U22	U33	U12	U13	U23
C1	0.020 (2)	0.0198 (19)	0.019 (2)	0.0004 (15)	−0.0046 (16)	−0.0023 (16)
C2	0.0166 (19)	0.022 (2)	0.020 (2)	−0.0014 (15)	−0.0030 (15)	−0.0076 (15)
C3	0.020 (2)	0.0158 (19)	0.027 (2)	−0.0019 (15)	−0.0032 (16)	−0.0063 (16)
C4	0.019 (2)	0.0162 (18)	0.029 (2)	−0.0035 (15)	−0.0068 (17)	−0.0012 (16)
C5	0.024 (2)	0.023 (2)	0.026 (2)	−0.0050 (16)	−0.0072 (17)	0.0055 (17)
C6	0.0165 (19)	0.026 (2)	0.0133 (19)	−0.0017 (15)	−0.0024 (15)	−0.0039 (15)
C7	0.0130 (18)	0.0215 (19)	0.019 (2)	0.0014 (15)	−0.0071 (15)	−0.0027 (15)
C8	0.0145 (18)	0.0200 (19)	0.017 (2)	−0.0006 (15)	−0.0037 (15)	−0.0004 (15)
C9	0.0177 (19)	0.0184 (19)	0.019 (2)	0.0008 (15)	−0.0025 (15)	−0.0004 (15)
C10	0.032 (2)	0.0191 (19)	0.0123 (19)	0.0004 (17)	0.0038 (17)	−0.0019 (15)
C11	0.020 (2)	0.0167 (19)	0.021 (2)	0.0004 (15)	−0.0006 (16)	−0.0068 (15)
C12	0.0152 (18)	0.0160 (18)	0.022 (2)	0.0006 (15)	0.0008 (15)	0.0017 (15)
C13	0.0128 (18)	0.0232 (19)	0.018 (2)	−0.0009 (15)	−0.0041 (15)	0.0017 (16)
C14	0.023 (2)	0.029 (2)	0.014 (2)	−0.0046 (17)	0.0010 (16)	0.0006 (16)
C15	0.0192 (19)	0.022 (2)	0.023 (2)	−0.0018 (16)	−0.0013 (16)	−0.0082 (16)
C16	0.0161 (19)	0.0153 (18)	0.028 (2)	−0.0011 (15)	−0.0049 (16)	0.0000 (16)
C17	0.0068 (17)	0.0229 (19)	0.021 (2)	−0.0022 (14)	−0.0032 (14)	0.0007 (15)
C18	0.0106 (17)	0.0219 (19)	0.0188 (19)	−0.0006 (14)	−0.0037 (15)	−0.0023 (15)
C19	0.0087 (17)	0.0237 (19)	0.019 (2)	−0.0008 (15)	−0.0023 (14)	−0.0016 (15)
C20	0.022 (2)	0.0102 (17)	0.021 (2)	0.0001 (15)	−0.0038 (16)	−0.0012 (15)
Cl1	0.0431 (6)	0.0251 (5)	0.0207 (5)	−0.0030 (4)	0.0021 (4)	−0.0090 (4)
Cl2	0.0445 (6)	0.0278 (5)	0.0170 (5)	−0.0053 (4)	−0.0006 (4)	−0.0009 (4)
Cl3	0.0300 (5)	0.0170 (5)	0.0251 (5)	0.0009 (4)	−0.0006 (4)	0.0019 (4)
Cl4	0.0426 (6)	0.0176 (5)	0.0297 (6)	−0.0056 (4)	−0.0077 (5)	−0.0008 (4)
N1	0.0214 (16)	0.0166 (15)	0.0173 (17)	0.0003 (13)	−0.0044 (13)	−0.0005 (13)
N2	0.0186 (16)	0.0175 (16)	0.0202 (17)	−0.0007 (13)	−0.0011 (13)	−0.0023 (13)
O1	0.0448 (18)	0.0228 (14)	0.0167 (14)	0.0110 (13)	−0.0039 (13)	−0.0015 (11)
O2	0.0441 (18)	0.0280 (15)	0.0284 (16)	−0.0120 (13)	−0.0078 (14)	−0.0041 (12)
O3	0.0171 (14)	0.0299 (14)	0.0196 (14)	0.0019 (11)	−0.0063 (11)	−0.0047 (11)
O4	0.0284 (15)	0.0272 (15)	0.0289 (16)	−0.0032 (12)	0.0019 (13)	0.0085 (12)
O5	0.0471 (18)	0.0223 (14)	0.0319 (17)	0.0073 (13)	−0.0161 (14)	−0.0108 (12)
O6	0.0202 (15)	0.0234 (15)	0.060 (2)	−0.0003 (12)	−0.0006 (14)	−0.0041 (13)
O7	0.050 (2)	0.075 (3)	0.132 (4)	−0.030 (2)	0.031 (2)	−0.055 (3)
Zn1	0.0206 (2)	0.0172 (2)	0.0168 (2)	−0.00023 (17)	−0.00297 (17)	−0.00061 (17)

C1—N1	1.316 (4)	C13—H13	0.9300
C1—C2	1.399 (5)	C14—C15	1.365 (5)
C1—H1	0.9300	C14—C19	1.419 (5)
C2—C3	1.352 (5)	C14—H14	0.9300
C2—Cl1	1.725 (4)	C15—C16	1.400 (5)
C3—C9	1.407 (5)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.366 (5)
C4—C5	1.359 (5)	C16—Cl4	1.739 (3)
C4—C9	1.414 (5)	C17—C18	1.414 (5)
C4—H4	0.9300	C17—C20	1.514 (5)
C5—C6	1.406 (5)	C18—N2	1.376 (4)
C5—H5	0.9300	C18—C19	1.415 (5)
C6—C7	1.374 (5)	C20—O4	1.237 (4)
C6—Cl2	1.732 (4)	C20—O3	1.261 (4)
C7—C8	1.421 (5)	N1—Zn1	2.211 (3)
C7—C10	1.504 (5)	O1—Zn1	1.978 (2)
C8—N1	1.377 (4)	O3—Zn1	1.960 (2)
C8—C9	1.419 (5)	O5—Zn1	2.101 (2)
C10—O2	1.231 (4)	O5—H5A	0.85
C10—O1	1.301 (4)	O5—H5B	0.86
C11—N2	1.310 (4)	O6—Zn1	1.982 (2)
C11—C12	1.410 (5)	O6—H6A	0.85
C11—H11	0.9300	O6—H6B	0.85
C12—C13	1.356 (5)	O7—H7B	0.85
C12—Cl3	1.727 (3)	O7—H7C	0.85
C13—C19	1.409 (5)
N1—C1—C2	123.4 (3)	C14—C15—C16	119.8 (3)
N1—C1—H1	118.3	C14—C15—H15	120.1
C2—C1—H1	118.3	C16—C15—H15	120.1
C3—C2—C1	119.8 (3)	C17—C16—C15	122.2 (3)
C3—C2—Cl1	121.7 (3)	C17—C16—Cl4	119.5 (3)
C1—C2—Cl1	118.5 (3)	C15—C16—Cl4	118.2 (3)
C2—C3—C9	119.2 (3)	C16—C17—C18	118.8 (3)
C2—C3—H3	120.4	C16—C17—C20	123.6 (3)
C9—C3—H3	120.4	C18—C17—C20	117.3 (3)
C5—C4—C9	120.5 (3)	N2—C18—C17	118.0 (3)
C5—C4—H4	119.7	N2—C18—C19	122.2 (3)
C9—C4—H4	119.7	C17—C18—C19	119.9 (3)
C4—C5—C6	119.7 (3)	C13—C19—C18	118.2 (3)
C4—C5—H5	120.1	C13—C19—C14	122.8 (3)
C6—C5—H5	120.1	C18—C19—C14	119.0 (3)
C7—C6—C5	122.6 (3)	O4—C20—O3	125.9 (3)
C7—C6—Cl2	120.7 (3)	O4—C20—C17	121.5 (3)
C5—C6—Cl2	116.7 (3)	O3—C20—C17	112.6 (3)
C6—C7—C8	117.8 (3)	C1—N1—C8	118.3 (3)
C6—C7—C10	121.9 (3)	C1—N1—Zn1	115.1 (2)
C8—C7—C10	120.1 (3)	C8—N1—Zn1	123.8 (2)
N1—C8—C9	121.0 (3)	C11—N2—C18	117.6 (3)
N1—C8—C7	118.9 (3)	C10—O1—Zn1	117.0 (2)
C9—C8—C7	120.1 (3)	C20—O3—Zn1	123.7 (2)
C3—C9—C4	122.6 (3)	Zn1—O5—H5A	124.5
C3—C9—C8	118.3 (3)	Zn1—O5—H5B	109.3
C4—C9—C8	119.1 (3)	H5A—O5—H5B	123.2
O2—C10—O1	124.4 (3)	Zn1—O6—H6A	119.1
O2—C10—C7	118.4 (3)	Zn1—O6—H6B	101.5
O1—C10—C7	117.2 (3)	H6A—O6—H6B	129.9
N2—C11—C12	123.4 (3)	H7B—O7—H7C	110.1
N2—C11—H11	118.3	O3—Zn1—O1	147.92 (11)
C12—C11—H11	118.3	O3—Zn1—O6	101.43 (11)
C13—C12—C11	120.2 (3)	O1—Zn1—O6	110.65 (12)
C13—C12—Cl3	120.9 (3)	O3—Zn1—O5	86.43 (10)
C11—C12—Cl3	118.9 (3)	O1—Zn1—O5	90.82 (10)
C12—C13—C19	118.4 (3)	O6—Zn1—O5	94.10 (11)
C12—C13—H13	120.8	O3—Zn1—N1	87.67 (10)
C19—C13—H13	120.8	O1—Zn1—N1	88.61 (10)
C15—C14—C19	120.3 (3)	O6—Zn1—N1	97.37 (11)
C15—C14—H14	119.8	O5—Zn1—N1	167.94 (11)
C19—C14—H14	119.8

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O1i	0.85	2.05	2.889 (4)	166
O5—H5B···N2	0.86	2.16	3.002 (4)	169
O6—H6A···O4ii	0.85	1.78	2.628 (4)	174
O6—H6B···O7iii	0.85	1.87	2.677 (4)	156
O7—H7B···O2iv	0.85	2.04	2.827 (4)	153
O7—H7C···O1v	0.85	2.25	3.029 (4)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O1i	0.85	2.05	2.889 (4)	166
O5—H5B⋯N2	0.86	2.16	3.002 (4)	169
O6—H6A⋯O4ii	0.85	1.78	2.628 (4)	174
O6—H6B⋯O7iii	0.85	1.87	2.677 (4)	156
O7—H7B⋯O2iv	0.85	2.04	2.827 (4)	153
O7—H7C⋯O1v	0.85	2.25	3.029 (4)	153

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