Aqua-(imino-diacetato-κO,N,O')(1,10-phenanthroline-κN,N')zinc(II) sesquihydrate.

The imino-diacetate dianion in the title compound, [Zn(C(4)H(5)NO(4))(C(12)H(8)N(2))(H(2)O)]·1.5H(2)O, chelates to the Zn(II) center with its N and two O atoms. The metal atom is also chelated by the N-heterocycle and coordinated by one water molecule, leading to a distorted octahedral environment. The dianion, and coordinated and uncoordinated water mol-ecules inter-act through O-H⋯O hydrogen bonds, generating a three-dimensional network. One of the two uncoordinated water mol-ecules has half-site occupancy. The crystal studied was a non-merohedral twin with a 15% twin component.

Related literature

For the structure of zinc bis­[imino­diacetate­(1-)] tetra­hydrate, see: Sinkha et al. (1975 ▶). For the dihydrated adenine adduct of zinc imino­diacetate, see: n class="Species">Morel et al. (2003 ▶). For the use of PLATON to separate twin fractions from diffraction data, see: Spek (2003 ▶).

Experimental

Crystal data

[Zn(n class="Chemical">C4H5NO4)(C12H8N2)(H2O)]·1.5H2O

M = 421.70

Triclinic,

a = 6.5989 (1) Å

b = 10.6440 (1) Å

c = 11.5456 (2) Å

α = 95.156 (1)°

β = 91.845 (1)°

γ = 92.190 (1)°

V = 806.56 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.57 mm−1

T = 100 (2) K

0.35 × 0.25 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.610, T max = 0.799

7242 measured reflections

3640 independent reflections

3455 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.146

S = 1.22

3640 reflections

233 parameters

72 restraints

H-atom parameters constrained

Δρmax = 1.02 e Å−3

Δρmin = −0.88 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042141/xu2469sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042141/xu2469Isup2.hkl

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

[Zn(C4H5NO4)(C12H8N2)(H2O)]·1.5H2O	Z = 2
Mr = 421.70	F(000) = 434
Triclinic, P1	Dx = 1.736 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5989 (1) Å	Cell parameters from 6223 reflections
b = 10.6440 (1) Å	θ = 2.5–28.3°
c = 11.5456 (2) Å	µ = 1.57 mm−1
α = 95.156 (1)°	T = 100 K
β = 91.845 (1)°	Block, colorless
γ = 92.190 (1)°	0.35 × 0.25 × 0.15 mm
V = 806.56 (2) Å3

Bruker SMART APEX diffractometer	3640 independent reflections
Radiation source: fine-focus sealed tube	3455 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.610, Tmax = 0.799	k = −13→13
7242 measured reflections	l = −14→14

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.22	w = 1/[σ2(Fo2) + (0.0241P)2 + 4.8628P] where P = (Fo2 + 2Fc2)/3
3640 reflections	(Δ/σ)max = 0.001
233 parameters	Δρmax = 1.01 e Å−3
72 restraints	Δρmin = −0.88 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.30260 (7)	0.63033 (5)	0.84683 (4)	0.01073 (15)
O1	−0.0016 (5)	0.7036 (3)	0.8533 (3)	0.0154 (6)
O2	−0.1646 (5)	0.8841 (3)	0.8519 (4)	0.0242 (8)
O3	0.3125 (5)	0.6228 (3)	1.0256 (3)	0.0137 (6)
O4	0.3975 (5)	0.7409 (3)	1.1911 (3)	0.0168 (7)
O1W	0.6167 (5)	0.5782 (3)	0.8460 (3)	0.0137 (6)
H11	0.6902	0.6376	0.8795	0.021*
H12	0.6294	0.5131	0.8812	0.021*
O2W	0.5864 (6)	1.0151 (3)	0.7055 (3)	0.0270 (8)
H21	0.6601	0.9737	0.7475	0.040*
H22	0.5886	1.0902	0.7349	0.040*
O3W	0.7199 (12)	1.0113 (7)	0.4793 (7)	0.0287 (16)	0.50
H31	0.6705	1.0115	0.5455	0.043*	0.50
H32	0.7870	1.0790	0.4740	0.043*	0.50
N1	0.3717 (6)	0.8255 (3)	0.8921 (3)	0.0155 (8)
H1	0.4735	0.8496	0.8507	0.019*
N2	0.1966 (5)	0.4443 (4)	0.7994 (3)	0.0142 (7)
N3	0.3044 (5)	0.6254 (4)	0.6611 (3)	0.0157 (7)
C1	−0.0062 (7)	0.8228 (4)	0.8568 (4)	0.0153 (8)
C2	0.1934 (7)	0.8985 (4)	0.8650 (5)	0.0207 (10)
H2A	0.2137	0.9349	0.7901	0.025*
H2B	0.1849	0.9696	0.9259	0.025*
C3	0.4372 (7)	0.8367 (4)	1.0155 (4)	0.0178 (9)
H3A	0.3811	0.9141	1.0538	0.021*
H3B	0.5869	0.8478	1.0206	0.021*
C4	0.3754 (6)	0.7252 (4)	1.0842 (4)	0.0127 (8)
C5	0.1390 (6)	0.3577 (4)	0.8671 (4)	0.0149 (8)
H5	0.1355	0.3802	0.9485	0.018*
C6	0.0828 (7)	0.2336 (5)	0.8242 (5)	0.0200 (9)
H6	0.0424	0.1735	0.8760	0.024*
C7	0.0864 (7)	0.1993 (5)	0.7068 (4)	0.0198 (9)
H7	0.0504	0.1151	0.6768	0.024*
C9	0.1991 (4)	0.4127 (3)	0.67929 (18)	0.0146 (8)
C8	0.1450 (5)	0.2916 (2)	0.6299 (2)	0.0186 (9)
C10	0.1399 (5)	0.2654 (2)	0.5097 (3)	0.0265 (11)
H10	0.1029	0.1827	0.4759	0.032*
C11	0.1889 (5)	0.3603 (3)	0.43886 (18)	0.0271 (11)
H11A	0.1854	0.3423	0.3567	0.032*
C12	0.2430 (5)	0.4813 (3)	0.4883 (2)	0.0213 (10)
C13	0.2481 (4)	0.5075 (2)	0.6085 (2)	0.0168 (9)
C14	0.2936 (7)	0.5828 (6)	0.4185 (4)	0.0254 (11)
H14	0.2912	0.5683	0.3360	0.030*
C15	0.3446 (7)	0.6986 (5)	0.4710 (4)	0.0220 (10)
H15	0.3765	0.7668	0.4262	0.026*
C16	0.3497 (7)	0.7169 (5)	0.5941 (4)	0.0209 (10)
H16	0.3874	0.7985	0.6304	0.025*

	U11	U22	U33	U12	U13	U23
Zn1	0.0119 (2)	0.0110 (2)	0.0096 (2)	0.00101 (17)	0.00101 (17)	0.00212 (17)
O1	0.0118 (14)	0.0139 (14)	0.0205 (16)	−0.0007 (11)	0.0005 (12)	0.0029 (12)
O2	0.0160 (16)	0.0179 (16)	0.040 (2)	0.0051 (13)	0.0028 (15)	0.0070 (15)
O3	0.0180 (15)	0.0111 (14)	0.0121 (15)	0.0005 (12)	0.0027 (12)	0.0010 (11)
O4	0.0199 (16)	0.0168 (15)	0.0137 (15)	0.0026 (12)	−0.0020 (12)	0.0013 (12)
O1W	0.0139 (14)	0.0114 (14)	0.0162 (15)	−0.0003 (11)	−0.0003 (12)	0.0035 (12)
O2W	0.036 (2)	0.0172 (17)	0.0267 (19)	0.0008 (15)	−0.0018 (16)	−0.0029 (14)
O3W	0.038 (4)	0.023 (4)	0.026 (4)	0.005 (3)	0.006 (3)	0.003 (3)
N1	0.0130 (18)	0.0134 (17)	0.021 (2)	0.0021 (14)	0.0008 (14)	0.0051 (14)
N2	0.0089 (16)	0.0159 (18)	0.0175 (19)	0.0032 (13)	−0.0017 (14)	−0.0013 (14)
N3	0.0078 (16)	0.027 (2)	0.0135 (18)	0.0044 (14)	0.0017 (13)	0.0069 (15)
C1	0.014 (2)	0.017 (2)	0.016 (2)	0.0014 (16)	0.0028 (16)	0.0052 (17)
C2	0.013 (2)	0.014 (2)	0.037 (3)	0.0018 (16)	0.0014 (19)	0.0100 (19)
C3	0.023 (2)	0.0123 (19)	0.018 (2)	−0.0015 (17)	0.0011 (18)	−0.0002 (16)
C4	0.0091 (18)	0.0126 (19)	0.017 (2)	0.0027 (15)	0.0023 (15)	0.0016 (16)
C5	0.0088 (18)	0.019 (2)	0.016 (2)	0.0008 (15)	−0.0006 (15)	−0.0006 (16)
C6	0.016 (2)	0.018 (2)	0.027 (2)	0.0023 (17)	0.0023 (18)	0.0038 (18)
C7	0.014 (2)	0.019 (2)	0.025 (2)	0.0023 (17)	−0.0019 (18)	−0.0068 (18)
C9	0.0073 (18)	0.024 (2)	0.013 (2)	0.0044 (16)	0.0002 (15)	0.0001 (17)
C8	0.0083 (19)	0.024 (2)	0.023 (2)	0.0015 (16)	0.0000 (16)	−0.0039 (18)
C10	0.011 (2)	0.042 (3)	0.024 (2)	0.004 (2)	−0.0026 (18)	−0.012 (2)
C11	0.013 (2)	0.050 (3)	0.016 (2)	0.005 (2)	−0.0006 (17)	−0.006 (2)
C12	0.0075 (18)	0.041 (3)	0.016 (2)	0.0062 (18)	0.0046 (16)	0.0011 (19)
C13	0.0101 (19)	0.026 (2)	0.015 (2)	0.0059 (17)	0.0009 (15)	0.0034 (17)
C14	0.014 (2)	0.053 (3)	0.010 (2)	0.010 (2)	0.0018 (17)	0.008 (2)
C15	0.012 (2)	0.042 (3)	0.016 (2)	0.0095 (19)	0.0052 (16)	0.015 (2)
C16	0.013 (2)	0.033 (3)	0.018 (2)	0.0052 (18)	0.0019 (17)	0.0109 (19)

Zn1—O3	2.072 (3)	C2—H2B	0.9900
Zn1—N2	2.093 (4)	C3—C4	1.535 (6)
Zn1—N1	2.124 (4)	C3—H3A	0.9900
Zn1—N3	2.141 (4)	C3—H3B	0.9900
Zn1—O1W	2.166 (3)	C5—C6	1.401 (6)
Zn1—O1	2.182 (3)	C5—H5	0.9500
O1—C1	1.267 (5)	C6—C7	1.373 (7)
O2—C1	1.255 (5)	C6—H6	0.9500
O3—C4	1.278 (5)	C7—C8	1.433 (6)
O4—C4	1.233 (6)	C7—H7	0.9500
O1W—H11	0.8399	C9—C8	1.3900
O1W—H12	0.8400	C9—C13	1.3900
O2W—H21	0.8400	C8—C10	1.3900
O2W—H22	0.8400	C10—C11	1.3900
O3W—H31	0.8401	C10—H10	0.9500
O3W—H32	0.8399	C11—C12	1.3900
N1—C3	1.469 (6)	C11—H11A	0.9500
N1—C2	1.475 (6)	C12—C13	1.3900
N1—H1	0.8800	C12—C14	1.440 (6)
N2—C5	1.315 (6)	C14—C15	1.350 (8)
N2—C9	1.398 (4)	C14—H14	0.9500
N3—C16	1.329 (6)	C15—C16	1.415 (7)
N3—C13	1.376 (5)	C15—H15	0.9500
C1—C2	1.513 (6)	C16—H16	0.9500
C2—H2A	0.9900
O3—Zn1—N2	98.01 (14)	N1—C3—H3A	108.3
O3—Zn1—N1	83.15 (14)	C4—C3—H3A	108.3
N2—Zn1—N1	172.78 (14)	N1—C3—H3B	108.3
O3—Zn1—N3	175.75 (14)	C4—C3—H3B	108.3
N2—Zn1—N3	79.24 (16)	H3A—C3—H3B	107.4
N1—Zn1—N3	99.99 (16)	O4—C4—O3	125.7 (4)
O3—Zn1—O1W	88.31 (12)	O4—C4—C3	117.1 (4)
N2—Zn1—O1W	92.50 (13)	O3—C4—C3	117.2 (4)
N1—Zn1—O1W	94.66 (13)	N2—C5—C6	122.7 (4)
N3—Zn1—O1W	88.57 (13)	N2—C5—H5	118.6
O3—Zn1—O1	90.74 (12)	C6—C5—H5	118.6
N2—Zn1—O1	93.69 (13)	C7—C6—C5	119.5 (5)
N1—Zn1—O1	79.15 (13)	C7—C6—H6	120.3
N3—Zn1—O1	92.67 (13)	C5—C6—H6	120.3
O1W—Zn1—O1	173.81 (12)	C6—C7—C8	119.5 (4)
C1—O1—Zn1	114.4 (3)	C6—C7—H7	120.3
C4—O3—Zn1	114.8 (3)	C8—C7—H7	120.3
Zn1—O1W—H11	109.5	C8—C9—C13	120.0
Zn1—O1W—H12	109.4	C8—C9—N2	121.7 (2)
H11—O1W—H12	109.5	C13—C9—N2	118.2 (2)
H21—O2W—H22	108.3	C10—C8—C9	120.0
H31—O3W—H32	110.0	C10—C8—C7	122.4 (3)
C3—N1—C2	114.7 (4)	C9—C8—C7	117.5 (3)
C3—N1—Zn1	105.8 (3)	C8—C10—C11	120.0
C2—N1—Zn1	109.4 (3)	C8—C10—H10	120.0
C3—N1—H1	108.9	C11—C10—H10	120.0
C2—N1—H1	108.9	C12—C11—C10	120.0
Zn1—N1—H1	108.9	C12—C11—H11A	120.0
C5—N2—C9	119.1 (4)	C10—C11—H11A	120.0
C5—N2—Zn1	128.5 (3)	C13—C12—C11	120.0
C9—N2—Zn1	112.3 (3)	C13—C12—C14	118.0 (3)
C16—N3—C13	118.5 (4)	C11—C12—C14	122.0 (3)
C16—N3—Zn1	129.7 (4)	N3—C13—C12	121.9 (2)
C13—N3—Zn1	111.8 (2)	N3—C13—C9	118.1 (2)
O2—C1—O1	125.1 (4)	C12—C13—C9	120.0
O2—C1—C2	116.7 (4)	C15—C14—C12	119.5 (4)
O1—C1—C2	118.3 (4)	C15—C14—H14	120.2
N1—C2—C1	114.4 (4)	C12—C14—H14	120.2
N1—C2—H2A	108.7	C14—C15—C16	119.0 (5)
C1—C2—H2A	108.7	C14—C15—H15	120.5
N1—C2—H2B	108.7	C16—C15—H15	120.5
C1—C2—H2B	108.7	N3—C16—C15	123.0 (5)
H2A—C2—H2B	107.6	N3—C16—H16	118.5
N1—C3—C4	115.9 (4)	C15—C16—H16	118.5
O3—Zn1—O1—C1	95.8 (3)	Zn1—O3—C4—C3	−1.0 (5)
N2—Zn1—O1—C1	−166.1 (3)	N1—C3—C4—O4	−167.9 (4)
N1—Zn1—O1—C1	12.9 (3)	N1—C3—C4—O3	14.5 (6)
N3—Zn1—O1—C1	−86.8 (3)	C9—N2—C5—C6	1.0 (6)
N2—Zn1—O3—C4	179.4 (3)	Zn1—N2—C5—C6	−175.9 (3)
N1—Zn1—O3—C4	−7.8 (3)	N2—C5—C6—C7	−0.2 (7)
O1W—Zn1—O3—C4	87.1 (3)	C5—C6—C7—C8	−0.9 (7)
O1—Zn1—O3—C4	−86.8 (3)	C5—N2—C9—C8	−0.8 (5)
O3—Zn1—N1—C3	14.2 (3)	Zn1—N2—C9—C8	176.55 (15)
N3—Zn1—N1—C3	−162.9 (3)	C5—N2—C9—C13	176.0 (3)
O1W—Zn1—N1—C3	−73.6 (3)	Zn1—N2—C9—C13	−6.6 (3)
O1—Zn1—N1—C3	106.2 (3)	C13—C9—C8—C10	0.0
O3—Zn1—N1—C2	−110.0 (3)	N2—C9—C8—C10	176.8 (3)
N3—Zn1—N1—C2	72.9 (3)	C13—C9—C8—C7	−177.0 (3)
O1W—Zn1—N1—C2	162.3 (3)	N2—C9—C8—C7	−0.2 (4)
O1—Zn1—N1—C2	−17.9 (3)	C6—C7—C8—C10	−175.9 (3)
O3—Zn1—N2—C5	5.3 (4)	C6—C7—C8—C9	1.0 (5)
N3—Zn1—N2—C5	−178.0 (4)	C9—C8—C10—C11	0.0
O1W—Zn1—N2—C5	94.0 (4)	C7—C8—C10—C11	176.9 (3)
O1—Zn1—N2—C5	−85.9 (4)	C8—C10—C11—C12	0.0
O3—Zn1—N2—C9	−171.7 (2)	C10—C11—C12—C13	0.0
N3—Zn1—N2—C9	5.0 (2)	C10—C11—C12—C14	−179.6 (3)
O1W—Zn1—N2—C9	−83.1 (3)	C16—N3—C13—C12	1.8 (5)
O1—Zn1—N2—C9	97.0 (3)	Zn1—N3—C13—C12	−178.48 (15)
N2—Zn1—N3—C16	176.8 (4)	C16—N3—C13—C9	−179.4 (3)
N1—Zn1—N3—C16	4.1 (4)	Zn1—N3—C13—C9	0.3 (3)
O1W—Zn1—N3—C16	−90.4 (4)	C11—C12—C13—N3	178.8 (3)
O1—Zn1—N3—C16	83.5 (4)	C14—C12—C13—N3	−1.6 (4)
N2—Zn1—N3—C13	−2.9 (2)	C11—C12—C13—C9	0.0
N1—Zn1—N3—C13	−175.6 (2)	C14—C12—C13—C9	179.6 (3)
O1W—Zn1—N3—C13	89.9 (3)	C8—C9—C13—N3	−178.8 (3)
O1—Zn1—N3—C13	−96.2 (3)	N2—C9—C13—N3	4.2 (3)
Zn1—O1—C1—O2	174.2 (4)	C8—C9—C13—C12	0.0
Zn1—O1—C1—C2	−4.4 (5)	N2—C9—C13—C12	−176.9 (3)
C3—N1—C2—C1	−97.2 (5)	C13—C12—C14—C15	0.2 (5)
Zn1—N1—C2—C1	21.6 (5)	C11—C12—C14—C15	179.8 (3)
O2—C1—C2—N1	169.4 (4)	C12—C14—C15—C16	0.9 (7)
O1—C1—C2—N1	−11.9 (7)	C13—N3—C16—C15	−0.6 (6)
C2—N1—C3—C4	101.9 (4)	Zn1—N3—C16—C15	179.8 (3)
Zn1—N1—C3—C4	−18.9 (4)	C14—C15—C16—N3	−0.8 (7)
Zn1—O3—C4—O4	−178.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2w	0.88	2.64	3.388 (5)	143
O1w—H11···O1i	0.84	2.17	2.801 (4)	132
O1w—H12···O3ii	0.84	1.92	2.757 (4)	172
O2w—H21···O2i	0.84	1.98	2.815 (5)	177
O2w—H22···O4iii	0.84	1.92	2.756 (5)	177
O3w—H31···O2w	0.84	1.94	2.780 (9)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H11⋯O1i	0.84	2.17	2.801 (4)	132
O1w—H12⋯O3ii	0.84	1.92	2.757 (4)	172
O2w—H21⋯O2i	0.84	1.98	2.815 (5)	177
O2w—H22⋯O4iii	0.84	1.92	2.756 (5)	177
O3w—H31⋯O2w	0.84	1.94	2.780 (9)	174

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