6-Bromo-2-naphthol–piperazine (2/1)

Yan Tian; Deliang Cui

doi:10.1107/S1600536808036878

. 2008 Nov 13;64(Pt 12):o2334. doi: 10.1107/S1600536808036878

6-Bromo-2-naphthol–piperazine (2/1)

Yan Tian ^a, Deliang Cui ^a,^*

PMCID: PMC2960040 PMID: 21581309

Abstract

In the title compound, 2C₁₀H₇BrO·C₄H₁₀N₂, the piperazine (pip) molecule displays a chair conformation and is linked to two molecules of 6-bromo-2-naphthol (bno) via O—H⋯N hydrogen bonds. Weak N—H⋯O hydrogen bonds from pip to bno molecules result in chains propagating in [100]. The chains interact via C—H⋯π interactions.

Related literature

For related structures, see: Wang & Tang (2006a ▶,b ▶,c ▶); Wang et al. (2008 ▶).

Experimental

Crystal data

2C₁₀H₇BrO·C₄H₁₀N₂
M _r = 532.27
Monoclinic,
a = 10.1327 (4) Å
b = 16.2494 (7) Å
c = 14.3499 (5) Å
β = 108.238 (2)°
V = 2244.02 (15) Å³
Z = 4
Mo Kα radiation
μ = 3.63 mm⁻¹
T = 296 (2) K
0.30 × 0.30 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.409, T _max = 0.713
16751 measured reflections
5164 independent reflections
2857 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.107
S = 1.00
5164 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036878/hb2836sup1.cif

e-64-o2334-sup1.cif^{(22KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036878/hb2836Isup2.hkl

e-64-o2334-Isup2.hkl^{(252.9KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯N1	0.82	1.94	2.743 (4)	168
O2—H2B⋯N2ⁱ	0.83	1.88	2.694 (4)	163
N1—H1C⋯O2	0.83	2.47	3.235 (4)	152
N2—H2A⋯O1ⁱⁱ	0.77	2.50	3.184 (4)	149
C4—H4A⋯Cg5	0.93	2.77	3.471 (3)	133
C14—H14A⋯Cg2ⁱⁱⁱ	0.93	2.68	3.371 (3)	132
C16—H16A⋯Cg1ⁱⁱⁱ	0.93	2.90	3.570 (3)	130
C21—H21A⋯Cg2^iv	0.97	2.93	3.831 (3)	156

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg1, Cg2 and Cg5 are the centroids of atoms C1–C5,C10, C5–C10 and C15–C20, respectively.

Acknowledgments

This work was supported by the Starting Fund of Shandong University.

supplementary crystallographic information

Comment

During the past decade, the field of molecular co-crystals have received considerable attention, for example, the design, construction and properties of molecular co-crystals. Recently, many co-crystals containing some organic acids and bases, have been successfully prepared and characterized by some research groups (Wang et al., 2006a,b,c). Especially, co-crystals containing hydroxyl-naphthalene with some organic bases have been synthesized and characterized (Wang et al., 2008). As part of our investigations of co-crystals containing 6-bromo-2-naphthol (bno), we now report the structure of the co-crystal, (I), of bno and piperazine.

A view of the title structure is shown in Fig. 1. The asymmetric unit consists of two independent bno molecules and one independent molecule of piperazine. In the crystal structure of (I), the piperazine molecule display a chair conformation and links with two molecules of 6-bromo-2-naphthol via O—H···N hydrogen bonds. These motifs are extended to one-dimensional chains via intermolecular edge-to-face C—H···π packing interactions (Fig. 2 and Table 1).

Experimental

A mixture of bno (446 mg, 1 mmol) and piperazine (86 mg, 1 mmol) was dissolved in methanol (10 ml), which was left at room temperature. Some colourless plates of (I0 were obtained after ten days. Analysis found (%): C, 54.28; H, 4.53; N, 5.28; requires (%): C, 54.16; H, 4.54; N, 5.26.