Aqua-[N-phenyl-2-(quinolin-8-yl-oxy)acetamide]dinitratozinc(II).

In the title complex, [Zn(NO(3))(2)(C(17)H(14)N(2)O(2))(H(2)O)], the six-coordinated Zn atom is in a distorted octa-hedral geometry, the donor centers being two O atoms and one N atom from the tridentate organic ligand, a water O atom and two O atoms from two monodentate nitrate ions. In the crystal, O-H⋯O hydrogen bonds between the coordinated water mol-ecules and nitrate O atoms and N-H⋯O hydrogen bonds between the main ligand and nitrate O atoms consolidate the three-dimensional network.

Related literature

For the synthesis of N-phenyl-2-(quinolin-8-yl­oxy)acetamide, see: Li et al. (2005 ▶); Wu et al. (2006 ▶). For the crystal structure of the hydrate of this mol­ecule, see: Li et al. (2005 ▶). For the coordination ability of related amides to lanthanides, see: Cai & Tan (2002 ▶); Wu et al. (2006 ▶).

Experimental

Crystal data

[Zn(NO3)2(C17H14N2O2)(H2O)]

M = 485.71

Triclinic,

a = 7.9980 (14) Å

b = 9.5109 (16) Å

c = 13.359 (2) Å

α = 94.876 (2)°

β = 96.496 (2)°

γ = 106.031 (2)°

V = 963.2 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.34 mm−1

T = 296 K

0.30 × 0.19 × 0.11 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.745, T max = 0.863

10541 measured reflections

4030 independent reflections

3454 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.093

S = 1.05

4030 reflections

281 parameters

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S160053681000471X/bh2270sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000471X/bh2270Isup2.hkl

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

[Zn(NO3)2(C17H14N2O2)(H2O)]	Z = 2
Mr = 485.71	F(000) = 496
Triclinic, P1	Dx = 1.675 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9980 (14) Å	Cell parameters from 4639 reflections
b = 9.5109 (16) Å	θ = 2.6–26.4°
c = 13.359 (2) Å	µ = 1.34 mm−1
α = 94.876 (2)°	T = 296 K
β = 96.496 (2)°	Prism, colorless
γ = 106.031 (2)°	0.30 × 0.19 × 0.11 mm
V = 963.2 (3) Å3

Bruker SMART CCD diffractometer	4030 independent reflections
Radiation source: fine-focus sealed tube	3454 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 26.7°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −10→10
Tmin = 0.745, Tmax = 0.863	k = −11→11
10541 measured reflections	l = −16→16

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0544P)2 + 0.1851P] where P = (Fo2 + 2Fc2)/3
4030 reflections	(Δ/σ)max < 0.001
281 parameters	Δρmax = 0.66 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

	x	y	z	Uiso*/Ueq
Zn1	0.40610 (3)	0.96202 (3)	0.180722 (18)	0.03178 (10)
O1	0.3965 (2)	0.74601 (17)	0.24213 (12)	0.0397 (4)
O2	0.2694 (2)	0.78947 (17)	0.06551 (12)	0.0379 (4)
O3	0.1934 (2)	0.9611 (2)	0.25329 (13)	0.0468 (4)
O4	−0.0719 (3)	0.9596 (3)	0.26368 (17)	0.0721 (6)
O5	0.0289 (3)	0.9897 (3)	0.12235 (16)	0.0820 (8)
O6	0.4097 (3)	1.1192 (2)	0.08737 (14)	0.0524 (5)
O7	0.3915 (4)	1.2818 (2)	0.20478 (17)	0.0757 (7)
O8	0.3628 (4)	1.3175 (2)	0.04674 (17)	0.0769 (7)
O9	0.6309 (2)	0.9394 (2)	0.12457 (14)	0.0566 (5)
H9A	0.6102	0.9205	0.0626	0.085*
H9B	0.7372	0.9403	0.1513	0.085*
N1	0.5583 (2)	1.0166 (2)	0.32636 (13)	0.0337 (4)
N2	0.2226 (3)	0.5535 (2)	−0.00405 (15)	0.0401 (5)
H2	0.2306	0.4695	0.0117	0.048*
N3	0.0477 (3)	0.9699 (2)	0.21100 (16)	0.0447 (5)
N4	0.3863 (3)	1.2425 (2)	0.11447 (17)	0.0480 (5)
C1	0.6333 (3)	1.1531 (3)	0.36958 (19)	0.0450 (6)
H1	0.6103	1.2301	0.3375	0.054*
C2	0.7469 (4)	1.1865 (3)	0.4625 (2)	0.0530 (7)
H2A	0.7961	1.2840	0.4912	0.064*
C3	0.7839 (4)	1.0767 (3)	0.50957 (19)	0.0528 (7)
H3	0.8605	1.0985	0.5703	0.063*
C4	0.7068 (3)	0.9290 (3)	0.46704 (17)	0.0431 (6)
C5	0.7382 (4)	0.8075 (4)	0.5099 (2)	0.0566 (7)
H5	0.8126	0.8223	0.5711	0.068*
C6	0.6612 (4)	0.6687 (4)	0.4632 (2)	0.0608 (8)
H6	0.6842	0.5897	0.4927	0.073*
C7	0.5464 (4)	0.6413 (3)	0.37011 (19)	0.0510 (7)
H7	0.4958	0.5456	0.3383	0.061*
C8	0.5119 (3)	0.7573 (3)	0.32834 (17)	0.0370 (5)
C9	0.5925 (3)	0.9046 (3)	0.37403 (16)	0.0343 (5)
C10	0.3655 (3)	0.6234 (3)	0.16737 (18)	0.0411 (5)
H10A	0.2877	0.5363	0.1880	0.049*
H10B	0.4750	0.6033	0.1567	0.049*
C11	0.2808 (3)	0.6650 (2)	0.07116 (17)	0.0339 (5)
C12	0.1501 (3)	0.5535 (3)	−0.10558 (18)	0.0381 (5)
C13	0.1263 (4)	0.4259 (3)	−0.1706 (2)	0.0494 (6)
H13	0.1577	0.3465	−0.1465	0.059*
C14	0.0558 (4)	0.4166 (3)	−0.2714 (2)	0.0610 (8)
H14	0.0408	0.3311	−0.3150	0.073*
C15	0.0081 (4)	0.5329 (3)	−0.3068 (2)	0.0629 (8)
H15	−0.0394	0.5267	−0.3744	0.076*
C16	0.0308 (4)	0.6595 (3)	−0.2417 (2)	0.0604 (8)
H16	−0.0018	0.7382	−0.2661	0.072*
C17	0.1011 (4)	0.6711 (3)	−0.1408 (2)	0.0493 (6)
H17	0.1154	0.7566	−0.0974	0.059*

	U11	U22	U33	U12	U13	U23
Zn1	0.03517 (16)	0.03244 (16)	0.02720 (15)	0.01224 (11)	−0.00243 (10)	0.00149 (10)
O1	0.0471 (9)	0.0359 (9)	0.0332 (8)	0.0153 (7)	−0.0107 (7)	−0.0015 (7)
O2	0.0448 (9)	0.0303 (8)	0.0348 (8)	0.0113 (7)	−0.0075 (7)	−0.0007 (6)
O3	0.0357 (9)	0.0719 (12)	0.0367 (9)	0.0229 (8)	0.0013 (7)	0.0082 (8)
O4	0.0428 (11)	0.1124 (19)	0.0713 (15)	0.0334 (12)	0.0168 (10)	0.0182 (13)
O5	0.0611 (14)	0.148 (2)	0.0473 (13)	0.0476 (15)	−0.0026 (10)	0.0271 (14)
O6	0.0806 (13)	0.0421 (10)	0.0500 (11)	0.0342 (10)	0.0243 (10)	0.0164 (8)
O7	0.115 (2)	0.0597 (14)	0.0523 (13)	0.0335 (13)	0.0008 (12)	−0.0042 (11)
O8	0.126 (2)	0.0575 (13)	0.0664 (14)	0.0540 (14)	0.0119 (13)	0.0232 (11)
O9	0.0378 (10)	0.0931 (15)	0.0413 (10)	0.0280 (10)	0.0000 (8)	−0.0016 (10)
N1	0.0325 (10)	0.0397 (11)	0.0271 (9)	0.0100 (8)	−0.0001 (7)	0.0016 (8)
N2	0.0509 (12)	0.0290 (10)	0.0365 (11)	0.0114 (9)	−0.0060 (9)	−0.0010 (8)
N3	0.0375 (11)	0.0521 (13)	0.0450 (12)	0.0175 (9)	−0.0009 (9)	0.0022 (10)
N4	0.0587 (14)	0.0367 (11)	0.0504 (13)	0.0177 (10)	0.0046 (11)	0.0070 (10)
C1	0.0481 (14)	0.0432 (14)	0.0376 (13)	0.0074 (11)	0.0004 (11)	−0.0016 (11)
C2	0.0539 (16)	0.0532 (16)	0.0370 (14)	−0.0016 (13)	−0.0032 (12)	−0.0062 (12)
C3	0.0450 (15)	0.0700 (19)	0.0307 (13)	0.0029 (13)	−0.0070 (11)	−0.0007 (12)
C4	0.0370 (13)	0.0630 (16)	0.0257 (11)	0.0110 (11)	−0.0010 (9)	0.0032 (11)
C5	0.0592 (17)	0.079 (2)	0.0327 (13)	0.0256 (15)	−0.0087 (12)	0.0133 (14)
C6	0.077 (2)	0.068 (2)	0.0456 (16)	0.0351 (17)	−0.0035 (14)	0.0193 (14)
C7	0.0645 (17)	0.0495 (15)	0.0398 (14)	0.0212 (13)	−0.0035 (12)	0.0092 (12)
C8	0.0382 (12)	0.0444 (13)	0.0282 (11)	0.0142 (10)	−0.0012 (9)	0.0045 (9)
C9	0.0299 (11)	0.0461 (13)	0.0263 (11)	0.0110 (9)	0.0023 (8)	0.0043 (9)
C10	0.0516 (14)	0.0333 (12)	0.0362 (12)	0.0150 (10)	−0.0056 (10)	−0.0008 (10)
C11	0.0323 (11)	0.0328 (12)	0.0340 (12)	0.0080 (9)	−0.0006 (9)	0.0021 (9)
C12	0.0377 (12)	0.0352 (12)	0.0351 (12)	0.0043 (9)	−0.0016 (9)	−0.0008 (9)
C13	0.0568 (16)	0.0402 (14)	0.0447 (14)	0.0107 (12)	−0.0035 (12)	−0.0051 (11)
C14	0.072 (2)	0.0539 (17)	0.0426 (15)	0.0062 (14)	−0.0029 (14)	−0.0165 (13)
C15	0.075 (2)	0.0621 (19)	0.0345 (14)	0.0007 (15)	−0.0108 (13)	−0.0008 (13)
C16	0.073 (2)	0.0503 (17)	0.0489 (16)	0.0117 (14)	−0.0149 (14)	0.0106 (13)
C17	0.0614 (17)	0.0370 (13)	0.0413 (14)	0.0084 (12)	−0.0077 (12)	−0.0008 (11)

Zn1—O6	2.0231 (17)	C3—C4	1.408 (4)
Zn1—O3	2.0494 (17)	C3—H3	0.9300
Zn1—O9	2.0818 (17)	C4—C5	1.403 (4)
Zn1—O2	2.1110 (15)	C4—C9	1.418 (3)
Zn1—N1	2.1166 (17)	C5—C6	1.354 (4)
Zn1—O1	2.2612 (16)	C5—H5	0.9300
O1—C8	1.369 (3)	C6—C7	1.418 (4)
O1—C10	1.416 (3)	C6—H6	0.9300
O2—C11	1.220 (3)	C7—C8	1.358 (3)
O3—N3	1.264 (3)	C7—H7	0.9300
O4—N3	1.238 (3)	C8—C9	1.421 (3)
O5—N3	1.214 (3)	C10—C11	1.518 (3)
O6—N4	1.266 (3)	C10—H10A	0.9700
O7—N4	1.225 (3)	C10—H10B	0.9700
O8—N4	1.228 (3)	C12—C17	1.384 (4)
O9—H9A	0.8200	C12—C13	1.385 (3)
O9—H9B	0.8812	C13—C14	1.385 (4)
N1—C1	1.320 (3)	C13—H13	0.9300
N1—C9	1.360 (3)	C14—C15	1.370 (4)
N2—C11	1.339 (3)	C14—H14	0.9300
N2—C12	1.414 (3)	C15—C16	1.379 (4)
N2—H2	0.8600	C15—H15	0.9300
C1—C2	1.409 (4)	C16—C17	1.384 (4)
C1—H1	0.9300	C16—H16	0.9300
C2—C3	1.347 (4)	C17—H17	0.9300
C2—H2A	0.9300
O6—Zn1—O3	103.05 (7)	C5—C4—C3	124.3 (2)
O6—Zn1—O9	86.57 (8)	C5—C4—C9	119.0 (2)
O3—Zn1—O9	170.28 (7)	C3—C4—C9	116.6 (2)
O6—Zn1—O2	93.07 (7)	C6—C5—C4	120.6 (2)
O3—Zn1—O2	95.75 (7)	C6—C5—H5	119.7
O9—Zn1—O2	85.04 (7)	C4—C5—H5	119.7
O6—Zn1—N1	120.13 (8)	C5—C6—C7	121.5 (3)
O3—Zn1—N1	86.60 (7)	C5—C6—H6	119.3
O9—Zn1—N1	87.29 (7)	C7—C6—H6	119.3
O2—Zn1—N1	145.38 (7)	C8—C7—C6	118.8 (3)
O6—Zn1—O1	163.42 (7)	C8—C7—H7	120.6
O3—Zn1—O1	86.10 (7)	C6—C7—H7	120.6
O9—Zn1—O1	84.93 (7)	C7—C8—O1	124.8 (2)
O2—Zn1—O1	72.04 (6)	C7—C8—C9	121.5 (2)
N1—Zn1—O1	73.67 (6)	O1—C8—C9	113.7 (2)
C8—O1—C10	119.01 (18)	N1—C9—C4	122.7 (2)
C8—O1—Zn1	114.78 (14)	N1—C9—C8	118.74 (19)
C10—O1—Zn1	114.98 (13)	C4—C9—C8	118.6 (2)
C11—O2—Zn1	120.10 (14)	O1—C10—C11	105.98 (18)
N3—O3—Zn1	124.92 (15)	O1—C10—H10A	110.5
N4—O6—Zn1	123.50 (16)	C11—C10—H10A	110.5
Zn1—O9—H9A	109.5	O1—C10—H10B	110.5
Zn1—O9—H9B	135.6	C11—C10—H10B	110.5
H9A—O9—H9B	114.8	H10A—C10—H10B	108.7
C1—N1—C9	118.3 (2)	O2—C11—N2	124.8 (2)
C1—N1—Zn1	123.78 (16)	O2—C11—C10	121.6 (2)
C9—N1—Zn1	117.69 (14)	N2—C11—C10	113.54 (19)
C11—N2—C12	129.5 (2)	C17—C12—C13	120.1 (2)
C11—N2—H2	115.3	C17—C12—N2	123.6 (2)
C12—N2—H2	115.3	C13—C12—N2	116.3 (2)
O5—N3—O4	122.1 (2)	C12—C13—C14	120.1 (3)
O5—N3—O3	120.4 (2)	C12—C13—H13	120.0
O4—N3—O3	117.5 (2)	C14—C13—H13	120.0
O7—N4—O8	123.7 (2)	C15—C14—C13	120.1 (3)
O7—N4—O6	119.6 (2)	C15—C14—H14	120.0
O8—N4—O6	116.7 (2)	C13—C14—H14	120.0
N1—C1—C2	122.5 (3)	C14—C15—C16	119.7 (3)
N1—C1—H1	118.7	C14—C15—H15	120.1
C2—C1—H1	118.7	C16—C15—H15	120.1
C3—C2—C1	119.7 (3)	C15—C16—C17	121.1 (3)
C3—C2—H2A	120.2	C15—C16—H16	119.5
C1—C2—H2A	120.2	C17—C16—H16	119.5
C2—C3—C4	120.1 (2)	C16—C17—C12	119.0 (3)
C2—C3—H3	119.9	C16—C17—H17	120.5
C4—C3—H3	119.9	C12—C17—H17	120.5

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9A···O6i	0.82	1.99	2.803 (3)	173
O9—H9B···O4ii	0.88	1.97	2.797 (3)	155
N2—H2···O8iii	0.86	2.07	2.869 (3)	155

Zn1—O6	2.0231 (17)
Zn1—O3	2.0494 (17)
Zn1—O9	2.0818 (17)
Zn1—O2	2.1110 (15)
Zn1—N1	2.1166 (17)
Zn1—O1	2.2612 (16)

O6—Zn1—O3	103.05 (7)
O6—Zn1—O9	86.57 (8)
O3—Zn1—O9	170.28 (7)
O6—Zn1—O2	93.07 (7)
O3—Zn1—O2	95.75 (7)
O9—Zn1—O2	85.04 (7)
O6—Zn1—N1	120.13 (8)
O3—Zn1—N1	86.60 (7)
O9—Zn1—N1	87.29 (7)
O2—Zn1—N1	145.38 (7)
O6—Zn1—O1	163.42 (7)
O3—Zn1—O1	86.10 (7)
O9—Zn1—O1	84.93 (7)
O2—Zn1—O1	72.04 (6)
N1—Zn1—O1	73.67 (6)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9A⋯O6i	0.82	1.99	2.803 (3)	173
O9—H9B⋯O4ii	0.88	1.97	2.797 (3)	155
N2—H2⋯O8iii	0.86	2.07	2.869 (3)	155

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