Morpholine–4-nitro­phenol (1/2)

Srinivasan Muralidharan; Yechuri Vidyalakshmi; Thothadri Srinivasan; Rengasamy Gopalakrishnan; Devadasan Velmurugan

doi:10.1107/S1600536812047174

. 2012 Nov 24;68(Pt 12):o3411. doi: 10.1107/S1600536812047174

Morpholine–4-nitrophenol (1/2)

Srinivasan Muralidharan ^a, Yechuri Vidyalakshmi ^a, Thothadri Srinivasan ^b, Rengasamy Gopalakrishnan ^a, Devadasan Velmurugan ^b,^*

PMCID: PMC3588998 PMID: 23476234

Abstract

In the title adduct, 2C₆H₅NO₃·C₄H₉NO, the morpholine ring adopts a chair conformation. The dihedral angle between the two nitrophenol rings is 69.47 (9)°. The nitro groups attached to the benzene rings make dihedral angles of 3.37 (16) and 3.14 (13)° in the two molecules of nitrophenol. The crystal structure is stabilized by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds and further consolidated by C—H⋯O interactions, resulting in a three-dimensional network.

Related literature

For the biological activity and synthesis of 4-(4-nitrophenyl)–morpholine derivatives, see: Wang et al. (2010 ▶). For a related structure, see: Wang et al. (2012 ▶).

Experimental

Crystal data

2C₆H₅NO₃·C₄H₉NO
M _r = 365.34
Monoclinic,
a = 18.0381 (7) Å
b = 5.5673 (2) Å
c = 17.4910 (7) Å
β = 91.606 (3)°
V = 1755.82 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.963, T _max = 0.973
16662 measured reflections
4354 independent reflections
2987 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.151
S = 1.05
4354 reflections
239 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Click here for additional data file.^{(26.3KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812047174/pv2605sup1.cif

e-68-o3411-sup1.cif^{(26.3KB, cif)}

Click here for additional data file.^{(209KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047174/pv2605Isup2.hkl

e-68-o3411-Isup2.hkl^{(209KB, 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
N3—H3B⋯O7ⁱ	0.77 (2)	2.46 (2)	3.000 (2)	129 (2)
N3—H3B⋯O4ⁱⁱ	0.77 (2)	2.36 (2)	3.032 (2)	147 (2)
C14—H14B⋯O4ⁱⁱ	0.97	2.55	3.322 (3)	136
O3—H3A⋯O6	0.82	1.77	2.590 (2)	173
O6—H6A⋯N3	0.82	1.93	2.607 (2)	140
C6—H6⋯O2ⁱⁱⁱ	0.93	2.53	3.424 (3)	161
C14—H14A⋯O5^iv	0.97	2.49	3.403 (3)	157
C15—H15B⋯O1^v	0.97	2.48	3.400 (3)	159
C16—H16B⋯O2^vi	0.97	2.56	3.441 (3)	152

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

Acknowledgments

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and TS also thanks the DST for an Inspire fellowship.

supplementary crystallographic information

Comment

4-(4-Nitrophenyl)morpholine derivatives are of great importance due to their anticancer activity (Wang et al., 2010). The title adduct is a key intermediate in the synthetic investigations of antitumor drugs. We report the preparation and crystal structure of the title adduct in this paper.

In the title adduct (Fig. 1), the morpholine ring adopts a chair conformation. The dihedral angle between the two nitrophenol rings is 69.47 (9)°. The nitro group attached with the benzene ring (C1–C6) makes a dihedral angle of 3.37 (16)°, while the other nitro group attached with the other benzene ring (C7–C12) makes a dihedral angle of 3.14 (13)°. The crystal structure is stabilzied by intermolecular interactions of the types N—H···O and O—H···O and further consolidated by C—H···O intermolcular hydrogen bonds (Tab. 1 & Fig. 2) resulting in a 3-dimensional network.

Experimental

Morpholine and 4-Nitrophenol were taken in equimolar (1:1) ratio using ethanol as solvent. The solution was filtered in a clean beaker and optimally closed. The solution was kept at room temperature. After two weeks, a product was obtained which was subsequently recrystallised from ethanol resulting in yellow coloured crystals suitable for X-ray diffraction.