Aqua­(imino­diacetato-κ3O,N,O′)(1,10-phenanthroline-κ2N,N′)zinc(II) sesquihydrate

Ng, H.L.; Ng, C.H.; Ng, S.W.

doi:10.1107/S1600536808042141

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page m89

doi:10.1107/S1600536808042141

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Aqua(iminodiacetato-κ³O,N,O′)(1,10-phenanthroline-κ²N,N′)zinc(II) sesquihydrate

Hwa Loong Ng,^a Chew Hee Ng ^a and Seik Weng Ng ^b ^*

^aFaculty of Engineering & Science, Universiti Tunku Abdul Rahman, Jalan Genting Kelang, 53100 Kuala Lumpur, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 10 December 2008; accepted 11 December 2008; online 17 December 2008)

The iminodiacetate dianion in the title compound, [Zn(C₄H₅NO₄)(C₁₂H₈N₂)(H₂O)]·1.5H₂O, 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 molecules interact through O—H⋯O hydrogen bonds, generating a three-dimensional network. One of the two uncoordinated water molecules 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: Morel et al. (2003 ). For the use of PLATON to separate twin fractions from diffraction data, see: Spek (2003 ).

Experimental

Crystal data

[Zn(C₄H₅NO₄)(C₁₂H₈N₂)(H₂O)]·1.5H₂O
M_r = 421.70
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.146
S = 1.22
3640 reflections
233 parameters
72 restraints
H-atom parameters constrained
Δρ_max = 1.02 e Å⁻³
Δρ_min = −0.88 e Å⁻³

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) x+1, y, z; (ii) -x+1, -y+1, -z+2; (iii) -x+1, -y+2, -z+2.

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 ).

Supporting information

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

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

checkCIF report

Related literature top

For the structure of zinc bis[iminodiacetate(1-)] tetrahydrate, see: Sinkha et al. (1975). For the dihydrated adenine adduct of zinc iminodiacetate, see: Morel et al. (2003). For the use of PLATON in de-twinning diffraction data, see: Spek (2003).

Experimental top

An methanol solution of zinc(II) nitrate hexahydrate (0.30 g, 1 mmol) and 1,10-phenanthroline (0.20 g, 1 mmol) was mixed with an aqueous solution of iminodiacetic acid (0.14 g, 1 mmol) and sodium hydroxide (0.08 g, 2 mmol). The mixture was briefly heated. The cool solution yielded a white solid. This was recrystallized from a water-methanol mixture to give colorless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: pubCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Zn(H₂O)(C₄H₅NO₄)(C₁₂H₈N₂)^.1.5H₂O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The O3w water molecule, which lies on a general position, has 0.5 occupancy.

Aqua(iminodiacetato-κ³O,N,O')(1,10-phenanthroline- κ²N,N')zinc(II) sesquihydrate top

Crystal data top

[Zn(C₄H₅NO₄)(C₁₂H₈N₂)(H₂O)]·1.5H₂O	Z = 2
M_r = 421.70	F(000) = 434
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART APEX diffractometer	3640 independent reflections
Radiation source: fine-focus sealed tube	3455 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.610, T_max = 0.799	k = −13→13
7242 measured reflections	l = −14→14

Refinement top

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(F_o²) + (0.0241P)² + 4.8628P] where P = (F_o² + 2F_c²)/3
3640 reflections	(Δ/σ)_max = 0.001
233 parameters	Δρ_max = 1.02 e Å⁻³
72 restraints	Δρ_min = −0.88 e Å⁻³

Crystal data top

[Zn(C₄H₅NO₄)(C₁₂H₈N₂)(H₂O)]·1.5H₂O	γ = 92.190 (1)°
M_r = 421.70	V = 806.56 (2) Å³
Triclinic, P1	Z = 2
a = 6.5989 (1) Å	Mo Kα radiation
b = 10.6440 (1) Å	µ = 1.57 mm⁻¹
c = 11.5456 (2) Å	T = 100 K
α = 95.156 (1)°	0.35 × 0.25 × 0.15 mm
β = 91.845 (1)°

Data collection top

Bruker SMART APEX diffractometer	3640 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3455 reflections with I > 2σ(I)
T_min = 0.610, T_max = 0.799	R_int = 0.025
7242 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	72 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.22	Δρ_max = 1.02 e Å⁻³
3640 reflections	Δρ_min = −0.88 e Å⁻³
233 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	[Zn(C₄H₅NO₄)(C₁₂H₈N₂)(H₂O)]·1.5H₂O
M_r	421.70
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.5989 (1), 10.6440 (1), 11.5456 (2)
α, β, γ (°)	95.156 (1), 91.845 (1), 92.190 (1)
V (Å³)	806.56 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.57
Crystal size (mm)	0.35 × 0.25 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.610, 0.799
No. of measured, independent and observed [I > 2σ(I)] reflections	7242, 3640, 3455
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.146, 1.22
No. of reflections	3640
No. of parameters	233
No. of restraints	72
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.02, −0.88

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), pubCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y+2, −z+2.

Acknowledgements

We thank Universiti Tunku Abdul Rahman and the University of Malaya for supporting this study.

References

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