(Cyclo­hexa­necarboxyl­ato)bis­(di-2-pyridylamine)zinc(II) nitrate monohydrate

Cai, Y.-J.; Yang, J.; Huang, P.; Lei, L.; Zeng, Q.-F.

doi:10.1107/S1600536809033443

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Pages m1144-m1145

doi:10.1107/S1600536809033443

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(Cyclohexanecarboxylato)bis(di-2-pyridylamine)zinc(II) nitrate monohydrate

Ying-Jie Cai,^a Jun Yang,^a Peng Huang,^a Lei Lei ^a and Qing-Fu Zeng ^a ^*

^aEngineering Research Center for Clean Production of Textile Dyeing and Printing, Ministry of Education, Wuhan 430073, People's Republic of China
^*Correspondence e-mail: qfzeng@wuse.edu.cn

(Received 15 August 2009; accepted 21 August 2009; online 29 August 2009)

In the title compound, [Zn(C₇H₁₁O₂)(C₁₀H₉N₃)₂]NO₃·H₂O, the Zn^II atom is five-coordinated by two bidentate di-2-pyridylamine ligands and one O atom from a cyclohexanecarboxyate anion, resulting in a ZnON₄ square-based pyramidal coordination for the metal ion with the O atom in one of the basal positions. In the crystal, the components interact by way of O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds.

Related literature

For background to acid and amine metal complexes and their molecular architectures, see: Yang et al. (2004 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Zn(C₇H₁₁O₂)(C₁₀H₉N₃)₂]NO₃·H₂O
M_r = 614.96
Triclinic, $[P \overline 1]$
a = 10.4856 (3) Å
b = 11.6116 (13) Å
c = 13.4876 (13) Å
α = 107.526 (3)°
β = 106.016 (3)°
γ = 99.706 (3)°
V = 1447.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.90 mm⁻¹
T = 296 K
0.32 × 0.26 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.761, T_max = 0.840
8944 measured reflections
6182 independent reflections
5178 reflections with I > 2σ(I)
R_int = 0.014
200 standard reflections every 3 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.109
S = 1.03
6182 reflections
386 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—N1	1.9984 (18)
Zn1—N3	2.0192 (19)
Zn1—N4	2.166 (2)
Zn1—N6	2.0405 (19)
Zn1—O2	1.9803 (16)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N12—H12⋯O6ⁱ	0.71 (3)	2.10 (3)	2.806 (3)	174 (3)
N11—H11A⋯O1ⁱⁱ	0.70 (2)	2.11 (3)	2.810 (3)	177 (3)
O6—H6B⋯N7ⁱⁱ	0.836 (10)	2.586 (14)	3.406 (4)	167 (3)
O6—H6B⋯O5ⁱⁱ	0.836 (10)	2.48 (3)	3.164 (4)	139 (3)
O6—H6B⋯O4ⁱⁱ	0.836 (10)	2.088 (12)	2.904 (4)	165 (3)
O6—H6A⋯O5ⁱⁱⁱ	0.838 (10)	1.971 (15)	2.787 (4)	164 (4)
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z+1; (iii) x, y, z+1.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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: 10.1107/S1600536809033443/hb5052sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809033443/hb5052Isup2.hkl

checkCIF report

Comment top

There has been much research interest in the acid and amine metal complexes due to their molecular architectures (e.g. Yang et al., 2004). In this work, we report here the crystal structure of the title compound, (I). In (I), all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). The Zn^II atom is five-coordinated by four N atoms from di-2-pyridylamine and one O atom from cyclohexanecarboxylic acid.

Related literature top

For background to acid and amine metal complexes and their molecular architectures, see: Yang et al. (2004). For reference structural data, see: Allen et al. (1987).

Experimental top

A mixture of di-2-pyridylamine (342 mg, 2 mmol), cyclohexanecarboxylic acid (256 mg, 2 mmol) and ZnNO₃.6H₂O (1 mmol, 297 mg) in methanol (10 ml) was stirred for 3 h. After keeping the filtrate in air for 8 d, colourless blocks of (I) were formed.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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 (I) showing 30% probability displacement ellipsoids.

(Cyclohexanecarboxylato)bis(di-2-pyridylamine)zinc(II) nitrate monohydrate top

Crystal data top

[Zn(C₇H₁₁O₂)(C₁₀H₉N₃)₂]NO₃·H₂O	Z = 2
M_r = 614.96	F(000) = 640
Triclinic, P1	D_x = 1.411 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.4856 (3) Å	Cell parameters from 25 reflections
b = 11.6116 (13) Å	θ = 9–12°
c = 13.4876 (13) Å	µ = 0.90 mm⁻¹
α = 107.526 (3)°	T = 296 K
β = 106.016 (3)°	Block, colorless
γ = 99.706 (3)°	0.32 × 0.26 × 0.20 mm
V = 1447.3 (2) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	5178 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.014
Graphite monochromator	θ_max = 27.0°, θ_min = 1.7°
ω/2θ scans	h = −12→13
Absorption correction: ψ scan (North et al., 1968)	k = −14→13
T_min = 0.761, T_max = 0.840	l = −17→17
8944 measured reflections	200 standard reflections every 3 reflections
6182 independent reflections	intensity decay: 1%

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0559P)² + 0.6885P] where P = (F_o² + 2F_c²)/3
6182 reflections	(Δ/σ)_max = 0.001
386 parameters	Δρ_max = 0.46 e Å⁻³
3 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Zn(C₇H₁₁O₂)(C₁₀H₉N₃)₂]NO₃·H₂O	γ = 99.706 (3)°
M_r = 614.96	V = 1447.3 (2) Å³
Triclinic, P1	Z = 2
a = 10.4856 (3) Å	Mo Kα radiation
b = 11.6116 (13) Å	µ = 0.90 mm⁻¹
c = 13.4876 (13) Å	T = 296 K
α = 107.526 (3)°	0.32 × 0.26 × 0.20 mm
β = 106.016 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	5178 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.014
T_min = 0.761, T_max = 0.840	200 standard reflections every 3 reflections
8944 measured reflections	intensity decay: 1%
6182 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	3 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.46 e Å⁻³
6182 reflections	Δρ_min = −0.34 e Å⁻³
386 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	0.1292 (3)	0.8840 (3)	0.4961 (3)	0.0615 (8)
H1A	0.0511	0.8886	0.4402	0.074*
H1B	0.2095	0.9486	0.5075	0.074*
C2	0.1004 (4)	0.9075 (3)	0.6045 (3)	0.0724 (10)
H2A	0.1822	0.9114	0.6623	0.087*
H2B	0.0798	0.9878	0.6267	0.087*
C3	−0.0192 (4)	0.8051 (4)	0.5925 (3)	0.0811 (11)
H3A	−0.0298	0.8188	0.6640	0.097*
H3B	−0.1035	0.8086	0.5422	0.097*
C4	0.0032 (3)	0.6775 (4)	0.5488 (3)	0.0757 (10)
H4A	0.0802	0.6703	0.6039	0.091*
H4B	−0.0783	0.6135	0.5363	0.091*
C5	0.0320 (3)	0.6546 (3)	0.4428 (3)	0.0630 (8)
H5A	−0.0489	0.6527	0.3853	0.076*
H5B	0.0505	0.5735	0.4198	0.076*
C6	0.1545 (3)	0.7559 (3)	0.4557 (2)	0.0450 (6)
H6	0.1607	0.7412	0.3819	0.054*
C7	0.2903 (2)	0.7493 (2)	0.52994 (18)	0.0344 (5)
C8	0.5875 (3)	0.8287 (3)	0.4789 (2)	0.0449 (6)
H8	0.5734	0.9075	0.5050	0.054*
C9	0.5912 (3)	0.7849 (3)	0.3745 (2)	0.0601 (8)
H9	0.5806	0.8332	0.3304	0.072*
C10	0.6110 (3)	0.6673 (3)	0.3351 (2)	0.0602 (8)
H10	0.6114	0.6346	0.2632	0.072*
C11	0.6299 (3)	0.5993 (3)	0.4021 (2)	0.0468 (6)
H11	0.6429	0.5198	0.3767	0.056*
C12	0.6293 (2)	0.6519 (2)	0.51007 (17)	0.0320 (4)
C13	0.7019 (2)	0.6277 (2)	0.69238 (19)	0.0367 (5)
C14	0.7804 (3)	0.5631 (3)	0.7447 (3)	0.0608 (8)
H14	0.7979	0.4917	0.7031	0.073*
C15	0.8314 (4)	0.6060 (4)	0.8583 (3)	0.0803 (11)
H15	0.8851	0.5649	0.8946	0.096*
C16	0.8021 (4)	0.7106 (4)	0.9178 (3)	0.0787 (11)
H16	0.8352	0.7411	0.9949	0.094*
C17	0.7240 (3)	0.7685 (3)	0.8619 (2)	0.0610 (8)
H17	0.7060	0.8400	0.9029	0.073*
C18	0.8081 (3)	1.0300 (3)	0.7532 (2)	0.0543 (7)
H18	0.8350	0.9632	0.7146	0.065*
C19	0.8960 (3)	1.1469 (3)	0.7940 (2)	0.0580 (7)
H19	0.9805	1.1598	0.7835	0.070*
C20	0.8562 (3)	1.2454 (3)	0.8512 (2)	0.0598 (8)
H20	0.9138	1.3267	0.8801	0.072*
C21	0.7314 (3)	1.2231 (2)	0.8654 (2)	0.0532 (7)
H21	0.7030	1.2891	0.9036	0.064*
C22	0.6474 (2)	1.1005 (2)	0.82200 (19)	0.0389 (5)
C23	0.4434 (2)	0.9739 (2)	0.84199 (18)	0.0366 (5)
C24	0.3436 (3)	0.9918 (3)	0.8921 (2)	0.0487 (6)
H24	0.3325	1.0716	0.9202	0.058*
C25	0.2633 (3)	0.8919 (3)	0.8994 (2)	0.0569 (7)
H25	0.1964	0.9027	0.9317	0.068*
C26	0.2822 (3)	0.7736 (3)	0.8580 (2)	0.0558 (7)
H26	0.2298	0.7041	0.8634	0.067*
C27	0.3796 (3)	0.7623 (3)	0.8094 (2)	0.0488 (6)
H27	0.3922	0.6830	0.7817	0.059*
H6A	0.524 (2)	0.360 (2)	0.983 (3)	0.081 (13)*
H6B	0.386 (2)	0.322 (3)	0.921 (3)	0.087 (13)*
N1	0.60361 (18)	0.76244 (17)	0.54675 (15)	0.0325 (4)
N3	0.6709 (2)	0.72807 (19)	0.74978 (16)	0.0398 (4)
N4	0.6839 (2)	1.00475 (19)	0.76529 (17)	0.0429 (5)
N6	0.4594 (2)	0.85966 (18)	0.79898 (16)	0.0375 (4)
N7	0.7893 (3)	0.5522 (2)	0.1219 (2)	0.0611 (6)
O1	0.30686 (18)	0.64659 (15)	0.53325 (15)	0.0455 (4)
O2	0.38469 (16)	0.85182 (15)	0.58651 (13)	0.0378 (4)
O3	0.8755 (3)	0.5011 (3)	0.1033 (3)	0.1179 (12)
O4	0.8103 (3)	0.6659 (2)	0.1560 (2)	0.0860 (8)
O5	0.6740 (3)	0.4912 (3)	0.1109 (3)	0.1178 (12)
O6	0.4564 (4)	0.2978 (2)	0.9418 (3)	0.0855 (8)
N11	0.6563 (2)	0.58533 (19)	0.57844 (16)	0.0363 (4)
N12	0.5229 (2)	1.0789 (2)	0.83921 (19)	0.0437 (5)
Zn1	0.54528 (3)	0.81698 (2)	0.67867 (2)	0.03606 (10)
H11A	0.667 (3)	0.528 (2)	0.553 (2)	0.027 (7)*
H12	0.505 (3)	1.135 (3)	0.861 (2)	0.037 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0498 (16)	0.0601 (17)	0.083 (2)	0.0269 (14)	0.0102 (15)	0.0427 (16)
C2	0.066 (2)	0.067 (2)	0.073 (2)	0.0456 (17)	0.0105 (16)	0.0076 (16)
C3	0.056 (2)	0.121 (3)	0.085 (2)	0.048 (2)	0.0373 (18)	0.040 (2)
C4	0.0456 (17)	0.090 (2)	0.116 (3)	0.0254 (16)	0.0374 (19)	0.060 (2)
C5	0.0374 (14)	0.0568 (17)	0.075 (2)	0.0109 (13)	0.0036 (14)	0.0128 (15)
C6	0.0397 (13)	0.0597 (16)	0.0391 (13)	0.0209 (12)	0.0104 (10)	0.0218 (12)
C7	0.0345 (11)	0.0421 (12)	0.0335 (11)	0.0168 (10)	0.0169 (9)	0.0154 (10)
C8	0.0436 (13)	0.0501 (14)	0.0537 (15)	0.0196 (11)	0.0218 (12)	0.0279 (12)
C9	0.0623 (18)	0.086 (2)	0.0517 (16)	0.0263 (16)	0.0260 (14)	0.0439 (16)
C10	0.0665 (19)	0.084 (2)	0.0364 (14)	0.0240 (16)	0.0255 (13)	0.0226 (14)
C11	0.0501 (15)	0.0530 (15)	0.0358 (12)	0.0157 (12)	0.0206 (11)	0.0086 (11)
C12	0.0262 (10)	0.0358 (11)	0.0314 (11)	0.0059 (8)	0.0114 (9)	0.0088 (9)
C13	0.0381 (12)	0.0401 (12)	0.0372 (12)	0.0152 (10)	0.0171 (10)	0.0152 (10)
C14	0.076 (2)	0.0703 (19)	0.0535 (16)	0.0487 (17)	0.0255 (15)	0.0284 (15)
C15	0.097 (3)	0.107 (3)	0.0597 (19)	0.068 (2)	0.0225 (19)	0.045 (2)
C16	0.090 (3)	0.118 (3)	0.0367 (15)	0.062 (2)	0.0150 (16)	0.0287 (17)
C17	0.0690 (19)	0.083 (2)	0.0332 (13)	0.0451 (17)	0.0160 (13)	0.0129 (13)
C18	0.0391 (14)	0.0557 (16)	0.0552 (16)	0.0088 (12)	0.0171 (12)	0.0042 (13)
C19	0.0411 (14)	0.0645 (18)	0.0552 (16)	−0.0017 (13)	0.0155 (13)	0.0138 (14)
C20	0.0596 (18)	0.0477 (16)	0.0573 (17)	−0.0043 (13)	0.0121 (14)	0.0167 (14)
C21	0.0624 (17)	0.0370 (13)	0.0538 (16)	0.0108 (12)	0.0182 (14)	0.0115 (12)
C22	0.0408 (12)	0.0394 (12)	0.0345 (12)	0.0118 (10)	0.0108 (10)	0.0124 (10)
C23	0.0392 (12)	0.0414 (12)	0.0290 (11)	0.0167 (10)	0.0111 (9)	0.0101 (9)
C24	0.0515 (15)	0.0582 (16)	0.0423 (13)	0.0253 (13)	0.0236 (12)	0.0141 (12)
C25	0.0533 (16)	0.078 (2)	0.0512 (16)	0.0224 (15)	0.0314 (14)	0.0246 (15)
C26	0.0579 (17)	0.0620 (17)	0.0546 (16)	0.0104 (14)	0.0288 (14)	0.0260 (14)
C27	0.0596 (16)	0.0433 (14)	0.0465 (14)	0.0137 (12)	0.0241 (13)	0.0157 (11)
N1	0.0304 (9)	0.0378 (10)	0.0343 (9)	0.0121 (8)	0.0149 (8)	0.0155 (8)
N3	0.0423 (11)	0.0490 (11)	0.0309 (9)	0.0230 (9)	0.0135 (8)	0.0121 (9)
N4	0.0361 (10)	0.0399 (11)	0.0455 (11)	0.0080 (8)	0.0160 (9)	0.0054 (9)
N6	0.0414 (11)	0.0384 (10)	0.0350 (10)	0.0139 (8)	0.0172 (8)	0.0113 (8)
N7	0.0612 (16)	0.0498 (15)	0.0746 (17)	0.0120 (12)	0.0294 (14)	0.0227 (13)
O1	0.0478 (10)	0.0371 (9)	0.0546 (10)	0.0202 (8)	0.0181 (8)	0.0160 (8)
O2	0.0335 (8)	0.0392 (9)	0.0431 (9)	0.0148 (7)	0.0138 (7)	0.0152 (7)
O3	0.101 (2)	0.087 (2)	0.199 (4)	0.0436 (18)	0.093 (3)	0.051 (2)
O4	0.0831 (18)	0.0619 (15)	0.116 (2)	0.0114 (13)	0.0389 (16)	0.0373 (14)
O5	0.0797 (19)	0.0729 (18)	0.176 (3)	−0.0024 (15)	0.059 (2)	0.0110 (19)
O6	0.094 (2)	0.0605 (15)	0.097 (2)	0.0444 (16)	0.0289 (17)	0.0132 (14)
N11	0.0434 (11)	0.0309 (10)	0.0356 (10)	0.0146 (9)	0.0171 (9)	0.0081 (9)
N12	0.0512 (13)	0.0375 (11)	0.0473 (12)	0.0212 (10)	0.0235 (10)	0.0116 (10)
Zn1	0.03508 (15)	0.03867 (16)	0.03545 (15)	0.01457 (11)	0.01437 (11)	0.01066 (11)

Geometric parameters (Å, º) top

C1—C6	1.518 (4)	C16—C17	1.356 (4)
C1—C2	1.529 (5)	C16—H16	0.9300
C1—H1A	0.9700	C17—N3	1.356 (3)
C1—H1B	0.9700	C17—H17	0.9300
C2—C3	1.511 (5)	C18—N4	1.351 (3)
C2—H2A	0.9700	C18—C19	1.357 (4)
C2—H2B	0.9700	C18—H18	0.9300
C3—C4	1.506 (5)	C19—C20	1.372 (4)
C3—H3A	0.9700	C19—H19	0.9300
C3—H3B	0.9700	C20—C21	1.367 (4)
C4—C5	1.497 (5)	C20—H20	0.9300
C4—H4A	0.9700	C21—C22	1.392 (4)
C4—H4B	0.9700	C21—H21	0.9300
C5—C6	1.519 (4)	C22—N4	1.326 (3)
C5—H5A	0.9700	C22—N12	1.383 (3)
C5—H5B	0.9700	C23—N6	1.337 (3)
C6—C7	1.527 (3)	C23—N12	1.373 (3)
C6—H6	0.9800	C23—C24	1.406 (3)
C7—O1	1.246 (3)	C24—C25	1.360 (4)
C7—O2	1.272 (3)	C24—H24	0.9300
C8—N1	1.356 (3)	C25—C26	1.389 (4)
C8—C9	1.360 (4)	C25—H25	0.9300
C8—H8	0.9300	C26—C27	1.361 (4)
C9—C10	1.382 (4)	C26—H26	0.9300
C9—H9	0.9300	C27—N6	1.357 (3)
C10—C11	1.365 (4)	C27—H27	0.9300
C10—H10	0.9300	N7—O3	1.204 (4)
C11—C12	1.402 (3)	N7—O4	1.218 (3)
C11—H11	0.9300	N7—O5	1.239 (4)
C12—N1	1.332 (3)	Zn1—N1	1.9984 (18)
C12—N11	1.373 (3)	Zn1—N3	2.0192 (19)
C13—N3	1.337 (3)	Zn1—N4	2.166 (2)
C13—N11	1.376 (3)	Zn1—N6	2.0405 (19)
C13—C14	1.395 (3)	Zn1—O2	1.9803 (16)
C14—C15	1.370 (4)	O6—H6A	0.838 (10)
C14—H14	0.9300	O6—H6B	0.836 (10)
C15—C16	1.374 (5)	N11—H11A	0.70 (2)
C15—H15	0.9300	N12—H12	0.71 (3)

C6—C1—C2	110.8 (2)	N3—C17—C16	123.7 (3)
C6—C1—H1A	109.5	N3—C17—H17	118.2
C2—C1—H1A	109.5	C16—C17—H17	118.2
C6—C1—H1B	109.5	N4—C18—C19	124.1 (3)
C2—C1—H1B	109.5	N4—C18—H18	118.0
H1A—C1—H1B	108.1	C19—C18—H18	118.0
C3—C2—C1	111.4 (3)	C18—C19—C20	117.9 (3)
C3—C2—H2A	109.3	C18—C19—H19	121.1
C1—C2—H2A	109.3	C20—C19—H19	121.1
C3—C2—H2B	109.3	C21—C20—C19	119.6 (3)
C1—C2—H2B	109.3	C21—C20—H20	120.2
H2A—C2—H2B	108.0	C19—C20—H20	120.2
C4—C3—C2	111.1 (2)	C20—C21—C22	119.2 (3)
C4—C3—H3A	109.4	C20—C21—H21	120.4
C2—C3—H3A	109.4	C22—C21—H21	120.4
C4—C3—H3B	109.4	N4—C22—N12	119.7 (2)
C2—C3—H3B	109.4	N4—C22—C21	121.8 (2)
H3A—C3—H3B	108.0	N12—C22—C21	118.6 (2)
C5—C4—C3	112.1 (3)	N6—C23—N12	121.9 (2)
C5—C4—H4A	109.2	N6—C23—C24	121.3 (2)
C3—C4—H4A	109.2	N12—C23—C24	116.8 (2)
C5—C4—H4B	109.2	C25—C24—C23	119.6 (2)
C3—C4—H4B	109.2	C25—C24—H24	120.2
H4A—C4—H4B	107.9	C23—C24—H24	120.2
C4—C5—C6	111.6 (3)	C24—C25—C26	119.4 (2)
C4—C5—H5A	109.3	C24—C25—H25	120.3
C6—C5—H5A	109.3	C26—C25—H25	120.3
C4—C5—H5B	109.3	C27—C26—C25	118.0 (3)
C6—C5—H5B	109.3	C27—C26—H26	121.0
H5A—C5—H5B	108.0	C25—C26—H26	121.0
C1—C6—C5	109.8 (2)	N6—C27—C26	123.9 (3)
C1—C6—C7	112.4 (2)	N6—C27—H27	118.0
C5—C6—C7	112.2 (2)	C26—C27—H27	118.0
C1—C6—H6	107.4	C12—N1—C8	117.9 (2)
C5—C6—H6	107.4	C12—N1—Zn1	123.08 (14)
C7—C6—H6	107.4	C8—N1—Zn1	117.45 (16)
O1—C7—O2	122.0 (2)	C13—N3—C17	117.2 (2)
O1—C7—C6	120.5 (2)	C13—N3—Zn1	123.65 (15)
O2—C7—C6	117.4 (2)	C17—N3—Zn1	119.08 (17)
N1—C8—C9	122.9 (3)	C22—N4—C18	117.5 (2)
N1—C8—H8	118.5	C22—N4—Zn1	122.70 (16)
C9—C8—H8	118.5	C18—N4—Zn1	119.52 (17)
C8—C9—C10	118.7 (3)	C23—N6—C27	117.6 (2)
C8—C9—H9	120.6	C23—N6—Zn1	122.08 (15)
C10—C9—H9	120.6	C27—N6—Zn1	117.11 (16)
C11—C10—C9	119.7 (2)	O3—N7—O4	122.9 (3)
C11—C10—H10	120.1	O3—N7—O5	121.4 (3)
C9—C10—H10	120.1	O4—N7—O5	115.7 (3)
C10—C11—C12	118.5 (3)	C7—O2—Zn1	108.91 (14)
C10—C11—H11	120.7	H6A—O6—H6B	109.5 (17)
C12—C11—H11	120.7	C12—N11—C13	129.1 (2)
N1—C12—N11	120.21 (19)	C12—N11—H11A	113 (2)
N1—C12—C11	122.0 (2)	C13—N11—H11A	115 (2)
N11—C12—C11	117.8 (2)	C23—N12—C22	131.3 (2)
N3—C13—N11	120.1 (2)	C23—N12—H12	114 (2)
N3—C13—C14	121.9 (2)	C22—N12—H12	113 (2)
N11—C13—C14	118.0 (2)	O2—Zn1—N1	89.03 (7)
C15—C14—C13	119.2 (3)	O2—Zn1—N3	162.61 (8)
C15—C14—H14	120.4	N1—Zn1—N3	88.38 (7)
C13—C14—H14	120.4	O2—Zn1—N6	85.24 (7)
C14—C15—C16	119.1 (3)	N1—Zn1—N6	172.28 (8)
C14—C15—H15	120.4	N3—Zn1—N6	95.55 (8)
C16—C15—H15	120.4	O2—Zn1—N4	100.52 (8)
C17—C16—C15	118.8 (3)	N1—Zn1—N4	99.74 (8)
C17—C16—H16	120.6	N3—Zn1—N4	96.86 (9)
C15—C16—H16	120.6	N6—Zn1—N4	86.42 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12···O6ⁱ	0.71 (3)	2.10 (3)	2.806 (3)	174 (3)
N11—H11A···O1ⁱⁱ	0.70 (2)	2.11 (3)	2.810 (3)	177 (3)
O6—H6B···N7ⁱⁱ	0.84 (1)	2.59 (1)	3.406 (4)	167 (3)
O6—H6B···O5ⁱⁱ	0.84 (1)	2.48 (3)	3.164 (4)	139 (3)
O6—H6B···O4ⁱⁱ	0.84 (1)	2.09 (1)	2.904 (4)	165 (3)
O6—H6A···O5ⁱⁱⁱ	0.84 (1)	1.97 (2)	2.787 (4)	164 (4)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₇H₁₁O₂)(C₁₀H₉N₃)₂]NO₃·H₂O
M_r	614.96
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	10.4856 (3), 11.6116 (13), 13.4876 (13)
α, β, γ (°)	107.526 (3), 106.016 (3), 99.706 (3)
V (Å³)	1447.3 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.90
Crystal size (mm)	0.32 × 0.26 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.761, 0.840
No. of measured, independent and observed [I > 2σ(I)] reflections	8944, 6182, 5178
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.109, 1.03
No. of reflections	6182
No. of parameters	386
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.34

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—N1	1.9984 (18)	Zn1—N6	2.0405 (19)
Zn1—N3	2.0192 (19)	Zn1—O2	1.9803 (16)
Zn1—N4	2.166 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12···O6ⁱ	0.71 (3)	2.10 (3)	2.806 (3)	174 (3)
N11—H11A···O1ⁱⁱ	0.70 (2)	2.11 (3)	2.810 (3)	177 (3)
O6—H6B···N7ⁱⁱ	0.836 (10)	2.586 (14)	3.406 (4)	167 (3)
O6—H6B···O5ⁱⁱ	0.836 (10)	2.48 (3)	3.164 (4)	139 (3)
O6—H6B···O4ⁱⁱ	0.836 (10)	2.088 (12)	2.904 (4)	165 (3)
O6—H6A···O5ⁱⁱⁱ	0.838 (10)	1.971 (15)	2.787 (4)	164 (4)

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

Acknowledgements

The project was supported by the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry, Educational Commission of Hubei Province (D20091703) and the Natural Science Foundation of Hubei Province (2008CDB038).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, H.-L., You, Z.-L. & Zhu, H.-L. (2004). Acta Cryst. E60, m1213–m1214. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 9| September 2009| Pages m1144-m1145

doi:10.1107/S1600536809033443

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(Cyclo­hexa­ne­carboxyl­ato)bis­­(di-2-pyridylamine)zinc(II) nitrate monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

(Cyclohexanecarboxylato)bis(di-2-pyridylamine)zinc(II) nitrate monohydrate