Aqua­(4,4′-dimethyl-2,2′-bipyridine-κ2N,N′)(nitrato-κO)(nitrato-κ2O,O′)zinc

Shirvan, S.A.; Haydari Dezfuli, S.

doi:10.1107/S1600536811050227

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages m1866-m1867

https://doi.org/10.1107/S1600536811050227

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Aqua(4,4′-dimethyl-2,2′-bipyridine-κ²N,N′)(nitrato-κO)(nitrato-κ²O,O′)zinc

Sadif A. Shirvan ^a ^* and Sara Haydari Dezfuli ^a

^aDepartment of Chemistry, Omidieh Branch, Islamic Azad University, Omidieh, Iran
^*Correspondence e-mail: sadif_shirvan1@yahoo.com

(Received 5 November 2011; accepted 22 November 2011; online 30 November 2011)

In the title compound, [Zn(NO₃)₂(C₁₂H₁₂N₂)(H₂O)], the Zn^II atom is six-coordinated in a distorted octahedral geometry by two N atoms from a chelating 4,4′-dimethyl-2,2′-bipyridine ligand, one water O atom, one O atom from a monodentate nitrate anion and two O atoms from a chelating nitrate anion. In the crystal, there are aromatic π–π contacts between the pyridine rings [centroid–centroid distances = 3.9577 (13) Å] and intermolecular O—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For related structures, see: Ahmadi et al. (2008 ); Alizadeh et al. (2010 ); Amani et al. (2009 ); Bellusci et al. (2008 ); Hojjat Kashani et al. (2008 ); Kalateh et al. (2008 , 2010 ); Sakamoto et al. (2004 ); Sofetis et al. (2006 ); Willett et al. (2001 ); Yoshikawa et al. (2003 ); Yousefi et al. (2008 ).

Experimental

Crystal data

[Zn(NO₃)₂(C₁₂H₁₂N₂)(H₂O)]
M_r = 391.66
Monoclinic, P 2₁ /n
a = 10.9266 (5) Å
b = 8.5717 (3) Å
c = 16.8073 (7) Å
β = 97.873 (4)°
V = 1559.33 (11) Å³
Z = 4
Mo Kα radiation
μ = 1.62 mm⁻¹
T = 120 K
0.5 × 0.4 × 0.31 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.460, T_max = 0.596
16739 measured reflections
4193 independent reflections
3596 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.084
S = 1.08
4193 reflections
227 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—N1	2.1157 (16)
Zn1—N2	2.0727 (17)
Zn1—O1	2.0965 (15)
Zn1—O2	2.5143 (16)
Zn1—O4	2.0340 (15)
Zn1—O7	2.0752 (15)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯O4ⁱ	0.85 (3)	1.90 (3)	2.724 (2)	163 (3)
O7—H7B⋯O3ⁱⁱ	0.87 (4)	1.94 (4)	2.799 (2)	174 (3)
C5—H5⋯O2ⁱⁱⁱ	0.93	2.53	3.420 (2)	161
C8—H8⋯O2ⁱⁱⁱ	0.93	2.36	3.230 (2)	156
C11—H11⋯O6^iv	0.93	2.44	3.284 (3)	151
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y, -z; (iv) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811050227/bt5709sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050227/bt5709Isup2.hkl

checkCIF report

Comment top

4,4'-Dimethyl-2,2'-bipyridine (4,4'-dmbipy), is a good bidentate ligand, and numerous complexes with 4,4'-dmbipy have been prepared, such as that of mercury (Kalateh et al., 2008; Yousefi et al., 2008), indium (Ahmadi et al., 2008), iron (Amani et al., 2009), platin (Hojjat Kashani et al., 2008), manganese (Sakamoto et al., 2004), silver (Bellusci et al., 2008), gallium (Sofetis et al., 2006), copper (Willett et al., 2001), iridium (Yoshikawa et al., 2003), cadmium (Kalateh et al., 2010) and zinc (Alizadeh et al., 2010). Here, we report the synthesis and structure of the title compound.

In the molecule of the title compound, (Fig. 1), the Zn^II atom is six-coordinated in a distorted octahedral configurations by two N atoms from the chelating 4,4'-dimethyl-2,2'-bipyridine, one O atom from water, one O atom from mono dentate nitrate anion and two O atoms from the chelating nitrate anion. The Zn—O and Zn—N bond lengths and angles are collected in Table 1.

In the crystal structure, intermolecular O—H···O and C—H···O hydrogen bonds (Table 2 & Fig. 2) link the molecules, in which they may be effective in the stabilization of the structure. There are also aromatic π-π contacts between the pyridine rings, Cg3···Cg4ⁱ [symmetry cods: (i) 1-X,-Y,-Z, where Cg3 and Cg4 are centroids of the rings (N1/C1—C3/C5—C6) and (N2/C7—C9/C11—C12), respectively] further stabilize the structure, with centroid-centroid distances of 3.9577 (13) Å.

Related literature top

For related structures, see: Ahmadi et al. (2008); Alizadeh et al. (2010); Amani et al. (2009); Bellusci et al. (2008); Hojjat Kashani et al. (2008); Kalateh et al. (2008, 2010); Sakamoto et al. (2004); Sofetis et al. (2006); Willett et al. (2001); Yoshikawa et al. (2003); Yousefi et al. (2008).

Experimental top

For the preparation of the title compound, a solution of 4,4'-dimethyl-2,2'-bipyridine (0.20 g, 1.10 mmol) in methanol (10 ml) was added to a solution of Zn(NO₃)₂.6H₂O (0.33 g, 1.10 mmol) in acetonitrile (10 ml) and the resulting colorless solution was stirred for 20 min at 313 K. This solution was left to evaporate slowly at room temperature. After one week, colorless prismatic crystals of the title compound were isolated (yield 0.33 g, 76.6%).

Structure description top

For related structures, see: Ahmadi et al. (2008); Alizadeh et al. (2010); Amani et al. (2009); Bellusci et al. (2008); Hojjat Kashani et al. (2008); Kalateh et al. (2008, 2010); Sakamoto et al. (2004); Sofetis et al. (2006); Willett et al. (2001); Yoshikawa et al. (2003); Yousefi et al. (2008).

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Unit-cell packing diagram for title compound.

Aqua(4,4'-dimethyl-2,2'-bipyridine-κ²N,N')(nitrato- κO)(nitrato-κ²O,O')zinc top

Crystal data top

[Zn(NO₃)₂(C₁₂H₁₂N₂)(H₂O)]	F(000) = 800
M_r = 391.66	D_x = 1.668 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 16739 reflections
a = 10.9266 (5) Å	θ = 2.1–29.2°
b = 8.5717 (3) Å	µ = 1.62 mm⁻¹
c = 16.8073 (7) Å	T = 120 K
β = 97.873 (4)°	Prism, colorless
V = 1559.33 (11) Å³	0.5 × 0.4 × 0.31 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3596 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
ω scans	θ_max = 29.2°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→14
T_min = 0.460, T_max = 0.596	k = −11→11
16739 measured reflections	l = −20→23
4193 independent reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0418P)² + 0.5925P] where P = (F_o² + 2F_c²)/3
4193 reflections	(Δ/σ)_max = 0.011
227 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

[Zn(NO₃)₂(C₁₂H₁₂N₂)(H₂O)]	V = 1559.33 (11) Å³
M_r = 391.66	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.9266 (5) Å	µ = 1.62 mm⁻¹
b = 8.5717 (3) Å	T = 120 K
c = 16.8073 (7) Å	0.5 × 0.4 × 0.31 mm
β = 97.873 (4)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4193 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3596 reflections with I > 2σ(I)
T_min = 0.460, T_max = 0.596	R_int = 0.054
16739 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.50 e Å⁻³
4193 reflections	Δρ_min = −0.65 e Å⁻³
227 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.66295 (19)	0.0759 (2)	0.21188 (13)	0.0223 (4)
H1	0.6598	0.1397	0.2563	0.027*
C2	0.77558 (18)	0.0545 (3)	0.18405 (13)	0.0235 (4)
H2	0.8465	0.1018	0.2102	0.028*
C3	0.78166 (17)	−0.0388 (2)	0.11638 (12)	0.0193 (4)
C4	0.90160 (18)	−0.0652 (3)	0.08374 (15)	0.0266 (4)
H4A	0.9514	−0.1379	0.1175	0.032*
H4B	0.945	0.0319	0.0826	0.032*
H4C	0.8849	−0.1066	0.0303	0.032*
C5	0.67277 (17)	−0.1087 (2)	0.08084 (12)	0.0180 (4)
H5	0.6732	−0.1716	0.0358	0.022*
C6	0.56307 (16)	−0.0844 (2)	0.11273 (11)	0.0154 (3)
C7	0.44364 (16)	−0.1594 (2)	0.07909 (11)	0.0157 (3)
C8	0.43269 (17)	−0.2639 (2)	0.01571 (11)	0.0178 (4)
H8	0.5013	−0.2879	−0.0092	0.021*
C9	0.31873 (18)	−0.3335 (2)	−0.01087 (12)	0.0188 (4)
C10	0.3034 (2)	−0.4469 (3)	−0.07953 (14)	0.0275 (4)
H10C	0.2531	−0.5329	−0.0668	0.033*
H10B	0.383	−0.4849	−0.0886	0.033*
H10A	0.2643	−0.3956	−0.1271	0.033*
C11	0.21939 (18)	−0.2944 (3)	0.02924 (12)	0.0220 (4)
H11	0.1423	−0.3396	0.0142	0.026*
C12	0.23656 (17)	−0.1886 (3)	0.09121 (12)	0.0227 (4)
H12	0.1693	−0.163	0.1171	0.027*
N1	0.55839 (15)	0.0081 (2)	0.17723 (10)	0.0179 (3)
N2	0.34579 (14)	−0.1203 (2)	0.11628 (10)	0.0180 (3)
N3	0.39927 (16)	0.3475 (2)	0.16842 (11)	0.0222 (3)
N4	0.44300 (15)	−0.0611 (2)	0.36776 (10)	0.0202 (3)
O1	0.41779 (13)	0.27826 (17)	0.23681 (8)	0.0216 (3)
O2	0.36572 (15)	0.2656 (2)	0.10800 (9)	0.0288 (3)
O3	0.41477 (16)	0.4902 (2)	0.16496 (11)	0.0316 (4)
O4	0.37061 (13)	−0.10009 (18)	0.30217 (9)	0.0224 (3)
O5	0.50246 (15)	0.06073 (19)	0.36678 (10)	0.0287 (3)
O6	0.44574 (16)	−0.1479 (2)	0.42578 (10)	0.0360 (4)
O7	0.19144 (14)	0.0920 (2)	0.20178 (10)	0.0242 (3)
H7A	0.169 (3)	0.185 (4)	0.1905 (18)	0.036 (8)*
H7B	0.156 (4)	0.067 (4)	0.243 (2)	0.058 (11)*
Zn1	0.37859 (2)	0.04435 (3)	0.207009 (13)	0.01710 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0188 (9)	0.0263 (11)	0.0217 (10)	−0.0027 (7)	0.0022 (7)	−0.0054 (8)
C2	0.0149 (8)	0.0291 (11)	0.0259 (10)	−0.0042 (8)	0.0002 (7)	−0.0003 (8)
C3	0.0117 (8)	0.0217 (9)	0.0246 (9)	0.0021 (7)	0.0031 (7)	0.0059 (8)
C4	0.0132 (8)	0.0314 (12)	0.0360 (12)	0.0009 (8)	0.0064 (8)	0.0022 (9)
C5	0.0152 (8)	0.0191 (9)	0.0203 (9)	0.0015 (7)	0.0046 (7)	0.0011 (7)
C6	0.0133 (8)	0.0175 (9)	0.0157 (8)	0.0017 (6)	0.0025 (6)	0.0032 (6)
C7	0.0106 (8)	0.0210 (9)	0.0158 (8)	−0.0002 (6)	0.0024 (6)	0.0025 (7)
C8	0.0152 (8)	0.0207 (9)	0.0182 (9)	0.0006 (7)	0.0047 (6)	0.0011 (7)
C9	0.0185 (9)	0.0212 (10)	0.0164 (9)	−0.0008 (7)	0.0009 (7)	0.0019 (7)
C10	0.0268 (10)	0.0263 (11)	0.0283 (11)	−0.0032 (9)	0.0003 (8)	−0.0058 (9)
C11	0.0142 (8)	0.0295 (11)	0.0215 (9)	−0.0022 (8)	−0.0006 (7)	0.0022 (8)
C12	0.0106 (8)	0.0368 (12)	0.0209 (9)	−0.0003 (8)	0.0026 (7)	0.0007 (8)
N1	0.0139 (7)	0.0210 (8)	0.0189 (8)	0.0010 (6)	0.0026 (6)	−0.0005 (6)
N2	0.0112 (7)	0.0250 (9)	0.0178 (8)	0.0015 (6)	0.0024 (5)	−0.0008 (6)
N3	0.0190 (8)	0.0264 (9)	0.0232 (9)	0.0038 (7)	0.0099 (6)	0.0031 (7)
N4	0.0160 (7)	0.0248 (9)	0.0189 (8)	0.0005 (6)	−0.0006 (6)	−0.0003 (6)
O1	0.0255 (7)	0.0218 (7)	0.0182 (7)	0.0021 (6)	0.0055 (5)	0.0024 (5)
O2	0.0269 (8)	0.0409 (10)	0.0195 (7)	0.0022 (7)	0.0063 (6)	−0.0033 (6)
O3	0.0360 (9)	0.0257 (8)	0.0370 (9)	0.0029 (7)	0.0185 (7)	0.0095 (7)
O4	0.0209 (7)	0.0262 (7)	0.0185 (7)	−0.0056 (6)	−0.0029 (5)	0.0013 (6)
O5	0.0281 (8)	0.0273 (8)	0.0299 (8)	−0.0102 (6)	0.0011 (6)	−0.0023 (6)
O6	0.0388 (9)	0.0395 (10)	0.0257 (8)	−0.0091 (8)	−0.0103 (7)	0.0133 (7)
O7	0.0182 (7)	0.0229 (8)	0.0333 (9)	0.0056 (6)	0.0102 (6)	0.0052 (6)
Zn1	0.01435 (11)	0.02035 (12)	0.01732 (12)	0.00208 (9)	0.00476 (7)	−0.00014 (9)

Geometric parameters (Å, º) top

C1—N1	1.342 (3)	C10—H10B	0.96
C1—C2	1.387 (3)	C10—H10A	0.96
C1—H1	0.93	C11—C12	1.374 (3)
C2—C3	1.399 (3)	C11—H11	0.93
C2—H2	0.93	C12—N2	1.344 (2)
C3—C5	1.392 (3)	C12—H12	0.93
C3—C4	1.506 (3)	Zn1—N1	2.1157 (16)
C4—H4A	0.96	Zn1—N2	2.0727 (17)
C4—H4B	0.96	N3—O3	1.238 (3)
C4—H4C	0.96	N3—O2	1.248 (2)
C5—C6	1.394 (3)	N3—O1	1.285 (2)
C5—H5	0.93	N4—O6	1.223 (2)
C6—N1	1.350 (3)	N4—O5	1.231 (2)
C6—C7	1.494 (2)	N4—O4	1.309 (2)
C7—N2	1.352 (2)	Zn1—O1	2.0965 (15)
C7—C8	1.385 (3)	Zn1—O2	2.5143 (16)
C8—C9	1.397 (3)	Zn1—O4	2.0340 (15)
C8—H8	0.93	Zn1—O7	2.0752 (15)
C9—C11	1.395 (3)	O7—H7A	0.84 (3)
C9—C10	1.501 (3)	O7—H7B	0.87 (4)
C10—H10C	0.96

N1—C1—C2	122.57 (19)	H10B—C10—H10A	109.5
N1—C1—H1	118.7	C12—C11—C9	119.35 (18)
C2—C1—H1	118.7	C12—C11—H11	120.3
C1—C2—C3	119.52 (18)	C9—C11—H11	120.3
C1—C2—H2	120.2	N2—C12—C11	123.24 (18)
C3—C2—H2	120.2	N2—C12—H12	118.4
C5—C3—C2	117.51 (17)	C11—C12—H12	118.4
C5—C3—C4	120.95 (19)	C1—N1—C6	118.65 (17)
C2—C3—C4	121.53 (18)	C1—N1—Zn1	126.65 (14)
C3—C4—H4A	109.5	C6—N1—Zn1	114.51 (12)
C3—C4—H4B	109.5	C12—N2—C7	118.13 (18)
H4A—C4—H4B	109.5	C12—N2—Zn1	125.71 (14)
C3—C4—H4C	109.5	C7—N2—Zn1	116.15 (13)
H4A—C4—H4C	109.5	O3—N3—O2	123.01 (19)
H4B—C4—H4C	109.5	O3—N3—O1	119.53 (18)
C3—C5—C6	120.01 (18)	O2—N3—O1	117.46 (18)
C3—C5—H5	120	O6—N4—O5	124.81 (17)
C6—C5—H5	120	O6—N4—O4	117.51 (17)
N1—C6—C5	121.72 (17)	O5—N4—O4	117.68 (17)
N1—C6—C7	115.43 (16)	N3—O1—Zn1	103.06 (12)
C5—C6—C7	122.85 (18)	N4—O4—Zn1	114.88 (12)
N2—C7—C8	121.69 (17)	Zn1—O7—H7A	116 (2)
N2—C7—C6	115.03 (17)	Zn1—O7—H7B	118 (2)
C8—C7—C6	123.26 (17)	H7A—O7—H7B	105 (3)
C7—C8—C9	120.09 (17)	O4—Zn1—N2	98.18 (7)
C7—C8—H8	120	O4—Zn1—O7	90.28 (6)
C9—C8—H8	120	N2—Zn1—O7	91.88 (6)
C11—C9—C8	117.48 (18)	O4—Zn1—O1	115.06 (6)
C11—C9—C10	120.98 (18)	N2—Zn1—O1	146.72 (6)
C8—C9—C10	121.54 (18)	O7—Zn1—O1	89.42 (6)
C9—C10—H10C	109.5	O4—Zn1—N1	103.76 (6)
C9—C10—H10B	109.5	N2—Zn1—N1	78.38 (6)
H10C—C10—H10B	109.5	O7—Zn1—N1	163.82 (7)
C9—C10—H10A	109.5	O1—Zn1—N1	91.77 (6)
H10C—C10—H10A	109.5

N1—C1—C2—C3	1.2 (3)	C6—C7—N2—Zn1	3.6 (2)
C1—C2—C3—C5	−1.2 (3)	O3—N3—O1—Zn1	−179.98 (15)
C1—C2—C3—C4	179.8 (2)	O2—N3—O1—Zn1	0.18 (19)
C2—C3—C5—C6	0.1 (3)	O6—N4—O4—Zn1	−176.91 (15)
C4—C3—C5—C6	179.08 (19)	O5—N4—O4—Zn1	3.7 (2)
C3—C5—C6—N1	1.1 (3)	N4—O4—Zn1—N2	147.48 (13)
C3—C5—C6—C7	−178.21 (18)	N4—O4—Zn1—O7	−120.58 (14)
N1—C6—C7—N2	2.1 (2)	N4—O4—Zn1—O1	−31.09 (15)
C5—C6—C7—N2	−178.61 (18)	N4—O4—Zn1—N1	67.52 (14)
N1—C6—C7—C8	−176.59 (18)	C12—N2—Zn1—O4	73.10 (18)
C5—C6—C7—C8	2.7 (3)	C7—N2—Zn1—O4	−107.81 (14)
N2—C7—C8—C9	−0.7 (3)	C12—N2—Zn1—O7	−17.46 (18)
C6—C7—C8—C9	177.87 (18)	C7—N2—Zn1—O7	161.64 (15)
C7—C8—C9—C11	−0.7 (3)	C12—N2—Zn1—O1	−109.26 (19)
C7—C8—C9—C10	179.82 (19)	C7—N2—Zn1—O1	69.83 (18)
C8—C9—C11—C12	1.3 (3)	C12—N2—Zn1—N1	175.56 (18)
C10—C9—C11—C12	−179.2 (2)	C7—N2—Zn1—N1	−5.34 (14)
C9—C11—C12—N2	−0.6 (3)	N3—O1—Zn1—O4	−170.58 (10)
C2—C1—N1—C6	0.0 (3)	N3—O1—Zn1—N2	12.00 (17)
C2—C1—N1—Zn1	−174.67 (16)	N3—O1—Zn1—O7	−80.55 (12)
C5—C6—N1—C1	−1.1 (3)	N3—O1—Zn1—N1	83.32 (12)
C7—C6—N1—C1	178.23 (17)	C1—N1—Zn1—O4	−83.06 (18)
C5—C6—N1—Zn1	174.17 (14)	C6—N1—Zn1—O4	102.12 (14)
C7—C6—N1—Zn1	−6.5 (2)	C1—N1—Zn1—N2	−178.76 (19)
C11—C12—N2—C7	−0.8 (3)	C6—N1—Zn1—N2	6.43 (14)
C11—C12—N2—Zn1	178.30 (16)	C1—N1—Zn1—O7	127.3 (2)
C8—C7—N2—C12	1.4 (3)	C6—N1—Zn1—O7	−47.5 (3)
C6—C7—N2—C12	−177.27 (17)	C1—N1—Zn1—O1	33.29 (18)
C8—C7—N2—Zn1	−177.75 (14)	C6—N1—Zn1—O1	−141.52 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O4ⁱ	0.85 (3)	1.90 (3)	2.724 (2)	163 (3)
O7—H7B···O3ⁱⁱ	0.87 (4)	1.94 (4)	2.799 (2)	174 (3)
C5—H5···O2ⁱⁱⁱ	0.93	2.53	3.420 (2)	161
C8—H8···O2ⁱⁱⁱ	0.93	2.36	3.230 (2)	156
C11—H11···O6^iv	0.93	2.44	3.284 (3)	151

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

Experimental details

Crystal data
Chemical formula	[Zn(NO₃)₂(C₁₂H₁₂N₂)(H₂O)]
M_r	391.66
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	10.9266 (5), 8.5717 (3), 16.8073 (7)
β (°)	97.873 (4)
V (Å³)	1559.33 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.62
Crystal size (mm)	0.5 × 0.4 × 0.31

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.460, 0.596
No. of measured, independent and observed [I > 2σ(I)] reflections	16739, 4193, 3596
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.084, 1.08
No. of reflections	4193
No. of parameters	227
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.65

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—N1	2.1157 (16)	Zn1—O2	2.5143 (16)
Zn1—N2	2.0727 (17)	Zn1—O4	2.0340 (15)
Zn1—O1	2.0965 (15)	Zn1—O7	2.0752 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O4ⁱ	0.85 (3)	1.90 (3)	2.724 (2)	163 (3)
O7—H7B···O3ⁱⁱ	0.87 (4)	1.94 (4)	2.799 (2)	174 (3)
C5—H5···O2ⁱⁱⁱ	0.93	2.53	3.420 (2)	161
C8—H8···O2ⁱⁱⁱ	0.93	2.36	3.230 (2)	156
C11—H11···O6^iv	0.93	2.44	3.284 (3)	151

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

Acknowledgements

We are grateful to the Islamic Azad University, Omidieh Branch for financial support.

References

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