Aqua-(4,4'-dimethyl-2,2'-bipyridine-κN,N')(nitrato-κO)(nitrato-κO,O')zinc.

In the title compound, [Zn(NO(3))(2)(C(12)H(12)N(2))(H(2)O)], the Zn(II) atom is six-coordinated in a distorted octa-hedral 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 inter-molecular 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(C12n class="Species">H12N2)(H2O)]

M = 391.66

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.084

S = 1.08

4193 reflections

227 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.65 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811050227/bt5709sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050227/bt5709Isup2.hkl

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

[Zn(NO3)2(C12H12N2)(H2O)]	F(000) = 800
Mr = 391.66	Dx = 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

Bruker APEXII CCD area-detector diffractometer	3596 reflections with I > 2σ(I)
graphite	Rint = 0.054
ω scans	θmax = 29.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→14
Tmin = 0.460, Tmax = 0.596	k = −11→11
16739 measured reflections	l = −20→23
4193 independent reflections

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(Fo2) + (0.0418P)2 + 0.5925P] where P = (Fo2 + 2Fc2)/3
4193 reflections	(Δ/σ)max = 0.011
227 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.65 e Å−3

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	0.66295 (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)

	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)

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)

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···O6iv	0.93	2.44	3.284 (3)	151

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⋯O6iv	0.93	2.44	3.284 (3)	151

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