organic compounds
Morpholine–4-nitrophenol (1/2)
aDepartment of Physics, Anna University, Chennai 600 025, India, and bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: shirai2011@gmail.com
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 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
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Refinement
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Data collection: APEX2 (Bruker, 2008); cell 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).
Supporting information
10.1107/S1600536812047174/pv2605sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812047174/pv2605Isup2.hkl
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.
All C-bound H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 and 0.97 Å, for aryl and methylene H-atoms, respectively. The hydroxyl H-atoms were included at geometrically calculated positions with O—H = 0.82 Å. The H-atom bonded to N3 was located from a difference map and allowed to refine freely. The Uiso(H) were allowed at 1.5Ueq(O) or 1.2Ueq(C/N).
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius. | |
Fig. 2. A view of the hydrogen bonds (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen- bonding were omitted for clarity. |
2C6H5NO3·C4H9NO | F(000) = 768 |
Mr = 365.34 | Dx = 1.382 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4354 reflections |
a = 18.0381 (7) Å | θ = 1.1–28.4° |
b = 5.5673 (2) Å | µ = 0.11 mm−1 |
c = 17.4910 (7) Å | T = 293 K |
β = 91.606 (3)° | Block, colourless |
V = 1755.82 (12) Å3 | 0.35 × 0.30 × 0.25 mm |
Z = 4 |
Bruker SMART APEXII area-detector diffractometer | 4354 independent reflections |
Radiation source: fine-focus sealed tube | 2987 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω and ϕ scans | θmax = 28.4°, θmin = 1.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −24→24 |
Tmin = 0.963, Tmax = 0.973 | k = −7→7 |
16662 measured reflections | l = −23→22 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0638P)2 + 0.4643P] where P = (Fo2 + 2Fc2)/3 |
4354 reflections | (Δ/σ)max < 0.001 |
239 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
2C6H5NO3·C4H9NO | V = 1755.82 (12) Å3 |
Mr = 365.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 18.0381 (7) Å | µ = 0.11 mm−1 |
b = 5.5673 (2) Å | T = 293 K |
c = 17.4910 (7) Å | 0.35 × 0.30 × 0.25 mm |
β = 91.606 (3)° |
Bruker SMART APEXII area-detector diffractometer | 4354 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 2987 reflections with I > 2σ(I) |
Tmin = 0.963, Tmax = 0.973 | Rint = 0.027 |
16662 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.151 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.45 e Å−3 |
4354 reflections | Δρmin = −0.30 e Å−3 |
239 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | 0.53902 (9) | 0.5777 (3) | 0.10103 (10) | 0.0565 (4) | |
C2 | 0.55081 (10) | 0.3693 (4) | 0.14223 (11) | 0.0648 (5) | |
H2 | 0.5982 | 0.3048 | 0.1474 | 0.078* | |
C3 | 0.49232 (10) | 0.2585 (4) | 0.17542 (12) | 0.0659 (5) | |
H3 | 0.5001 | 0.1191 | 0.2038 | 0.079* | |
C4 | 0.42092 (10) | 0.3533 (3) | 0.16694 (10) | 0.0560 (4) | |
C5 | 0.41037 (10) | 0.5620 (3) | 0.12451 (11) | 0.0616 (5) | |
H5 | 0.3630 | 0.6260 | 0.1183 | 0.074* | |
C6 | 0.46899 (10) | 0.6747 (4) | 0.09170 (11) | 0.0628 (5) | |
H6 | 0.4617 | 0.8148 | 0.0635 | 0.075* | |
C7 | 0.13017 (10) | 0.8918 (3) | 0.31527 (9) | 0.0553 (4) | |
C8 | 0.09076 (10) | 0.7063 (4) | 0.28005 (10) | 0.0588 (4) | |
H8 | 0.0404 | 0.6875 | 0.2884 | 0.071* | |
C9 | 0.12639 (9) | 0.5524 (3) | 0.23317 (10) | 0.0539 (4) | |
H9 | 0.0996 | 0.4294 | 0.2093 | 0.065* | |
C10 | 0.20240 (9) | 0.5739 (3) | 0.21978 (9) | 0.0469 (4) | |
C11 | 0.24071 (10) | 0.7647 (4) | 0.25620 (10) | 0.0585 (4) | |
H11 | 0.2911 | 0.7845 | 0.2483 | 0.070* | |
C12 | 0.20488 (11) | 0.9213 (3) | 0.30297 (10) | 0.0624 (5) | |
H12 | 0.2308 | 1.0470 | 0.3264 | 0.075* | |
C13 | 0.11073 (9) | 0.0465 (3) | 0.07932 (11) | 0.0572 (4) | |
H13A | 0.0692 | 0.1572 | 0.0801 | 0.069* | |
H13B | 0.1164 | −0.0247 | 0.1298 | 0.069* | |
C14 | 0.09471 (11) | −0.1474 (3) | 0.02155 (12) | 0.0629 (5) | |
H14A | 0.0513 | −0.2372 | 0.0364 | 0.076* | |
H14B | 0.0839 | −0.0750 | −0.0280 | 0.076* | |
C15 | 0.21931 (12) | −0.1788 (4) | −0.00757 (13) | 0.0739 (6) | |
H15A | 0.2090 | −0.1040 | −0.0568 | 0.089* | |
H15B | 0.2600 | −0.2907 | −0.0134 | 0.089* | |
C16 | 0.24145 (10) | 0.0101 (3) | 0.04962 (11) | 0.0594 (5) | |
H16A | 0.2553 | −0.0654 | 0.0979 | 0.071* | |
H16B | 0.2841 | 0.0973 | 0.0317 | 0.071* | |
N1 | 0.60131 (9) | 0.6983 (4) | 0.06695 (11) | 0.0732 (5) | |
N2 | 0.09282 (13) | 1.0491 (3) | 0.36639 (9) | 0.0775 (5) | |
O7 | 0.15556 (8) | −0.3055 (2) | 0.01578 (9) | 0.0733 (4) | |
O1 | 0.66276 (8) | 0.6053 (4) | 0.07188 (11) | 0.1022 (6) | |
O2 | 0.59056 (10) | 0.8873 (4) | 0.03293 (13) | 0.1106 (7) | |
O3 | 0.36561 (7) | 0.2375 (3) | 0.20120 (9) | 0.0792 (4) | |
H3A | 0.3265 | 0.3093 | 0.1929 | 0.119* | |
O4 | 0.12927 (12) | 1.2119 (3) | 0.39774 (9) | 0.1007 (6) | |
O5 | 0.02664 (12) | 1.0156 (4) | 0.37853 (11) | 0.1164 (7) | |
O6 | 0.23640 (6) | 0.4276 (2) | 0.17466 (7) | 0.0620 (3) | |
H6A | 0.2068 | 0.3287 | 0.1572 | 0.093* | |
N3 | 0.17917 (8) | 0.1798 (2) | 0.06111 (9) | 0.0483 (3) | |
H3B | 0.1748 (10) | 0.258 (3) | 0.0250 (11) | 0.055 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0503 (9) | 0.0618 (10) | 0.0574 (10) | 0.0096 (8) | 0.0024 (7) | −0.0051 (9) |
C2 | 0.0521 (9) | 0.0705 (12) | 0.0714 (12) | 0.0183 (9) | −0.0053 (8) | −0.0017 (10) |
C3 | 0.0634 (11) | 0.0604 (11) | 0.0731 (13) | 0.0134 (9) | −0.0087 (9) | 0.0083 (10) |
C4 | 0.0527 (9) | 0.0558 (10) | 0.0592 (10) | 0.0030 (8) | −0.0059 (8) | −0.0037 (8) |
C5 | 0.0475 (9) | 0.0645 (11) | 0.0726 (12) | 0.0143 (8) | −0.0027 (8) | 0.0050 (10) |
C6 | 0.0583 (10) | 0.0596 (11) | 0.0708 (12) | 0.0160 (8) | 0.0045 (9) | 0.0081 (9) |
C7 | 0.0746 (11) | 0.0519 (9) | 0.0389 (8) | 0.0103 (8) | −0.0055 (7) | −0.0029 (7) |
C8 | 0.0534 (9) | 0.0688 (11) | 0.0541 (10) | 0.0030 (8) | 0.0013 (7) | −0.0060 (9) |
C9 | 0.0514 (9) | 0.0542 (9) | 0.0560 (10) | −0.0084 (7) | −0.0001 (7) | −0.0106 (8) |
C10 | 0.0504 (8) | 0.0497 (8) | 0.0404 (8) | −0.0022 (7) | −0.0026 (6) | 0.0002 (7) |
C11 | 0.0559 (9) | 0.0685 (11) | 0.0510 (10) | −0.0146 (8) | −0.0030 (7) | −0.0055 (9) |
C12 | 0.0846 (13) | 0.0552 (10) | 0.0467 (9) | −0.0163 (9) | −0.0113 (9) | −0.0067 (8) |
C13 | 0.0520 (9) | 0.0584 (10) | 0.0615 (10) | 0.0025 (8) | 0.0093 (8) | 0.0002 (8) |
C14 | 0.0641 (11) | 0.0514 (10) | 0.0733 (12) | −0.0119 (8) | 0.0015 (9) | 0.0043 (9) |
C15 | 0.0754 (13) | 0.0680 (12) | 0.0786 (14) | 0.0166 (10) | 0.0104 (10) | −0.0227 (11) |
C16 | 0.0511 (9) | 0.0648 (11) | 0.0628 (11) | 0.0035 (8) | 0.0099 (8) | −0.0092 (9) |
N1 | 0.0579 (9) | 0.0808 (12) | 0.0816 (12) | 0.0131 (8) | 0.0145 (8) | 0.0011 (10) |
N2 | 0.1161 (16) | 0.0702 (11) | 0.0454 (9) | 0.0301 (11) | −0.0100 (9) | −0.0105 (8) |
O7 | 0.0931 (10) | 0.0374 (6) | 0.0891 (10) | −0.0001 (6) | −0.0031 (8) | −0.0037 (6) |
O1 | 0.0543 (8) | 0.1261 (15) | 0.1269 (14) | 0.0210 (9) | 0.0169 (8) | 0.0207 (12) |
O2 | 0.0830 (11) | 0.0936 (12) | 0.1573 (18) | 0.0169 (10) | 0.0437 (11) | 0.0417 (13) |
O3 | 0.0595 (8) | 0.0772 (9) | 0.1010 (11) | −0.0002 (7) | 0.0000 (7) | 0.0206 (9) |
O4 | 0.1836 (19) | 0.0604 (9) | 0.0576 (9) | 0.0131 (11) | −0.0061 (10) | −0.0163 (7) |
O5 | 0.1010 (14) | 0.1490 (18) | 0.0994 (13) | 0.0500 (13) | 0.0057 (11) | −0.0458 (13) |
O6 | 0.0515 (6) | 0.0723 (8) | 0.0619 (7) | 0.0003 (6) | −0.0010 (5) | −0.0193 (7) |
N3 | 0.0595 (8) | 0.0377 (7) | 0.0476 (8) | 0.0013 (6) | 0.0029 (6) | 0.0053 (6) |
C1—C2 | 1.379 (3) | C12—H12 | 0.9300 |
C1—C6 | 1.379 (2) | C13—N3 | 1.483 (2) |
C1—N1 | 1.451 (2) | C13—C14 | 1.501 (3) |
C2—C3 | 1.366 (3) | C13—H13A | 0.9700 |
C2—H2 | 0.9300 | C13—H13B | 0.9700 |
C3—C4 | 1.396 (2) | C14—O7 | 1.413 (2) |
C3—H3 | 0.9300 | C14—H14A | 0.9700 |
C4—O3 | 1.343 (2) | C14—H14B | 0.9700 |
C4—C5 | 1.389 (3) | C15—O7 | 1.419 (3) |
C5—C6 | 1.369 (3) | C15—C16 | 1.498 (3) |
C5—H5 | 0.9300 | C15—H15A | 0.9700 |
C6—H6 | 0.9300 | C15—H15B | 0.9700 |
C7—C12 | 1.380 (3) | C16—N3 | 1.486 (2) |
C7—C8 | 1.388 (3) | C16—H16A | 0.9700 |
C7—N2 | 1.433 (2) | C16—H16B | 0.9700 |
C8—C9 | 1.360 (2) | N1—O2 | 1.222 (2) |
C8—H8 | 0.9300 | N1—O1 | 1.224 (2) |
C9—C10 | 1.403 (2) | N2—O5 | 1.233 (3) |
C9—H9 | 0.9300 | N2—O4 | 1.238 (2) |
C10—O6 | 1.2998 (19) | O3—H3A | 0.8200 |
C10—C11 | 1.409 (2) | O6—H6A | 0.8200 |
C11—C12 | 1.370 (3) | N3—H3B | 0.77 (2) |
C11—H11 | 0.9300 | ||
C2—C1—C6 | 121.24 (17) | N3—C13—C14 | 111.17 (14) |
C2—C1—N1 | 119.60 (16) | N3—C13—H13A | 109.4 |
C6—C1—N1 | 119.16 (17) | C14—C13—H13A | 109.4 |
C3—C2—C1 | 119.50 (16) | N3—C13—H13B | 109.4 |
C3—C2—H2 | 120.2 | C14—C13—H13B | 109.4 |
C1—C2—H2 | 120.2 | H13A—C13—H13B | 108.0 |
C2—C3—C4 | 120.37 (18) | O7—C14—C13 | 111.16 (15) |
C2—C3—H3 | 119.8 | O7—C14—H14A | 109.4 |
C4—C3—H3 | 119.8 | C13—C14—H14A | 109.4 |
O3—C4—C5 | 123.20 (16) | O7—C14—H14B | 109.4 |
O3—C4—C3 | 117.78 (17) | C13—C14—H14B | 109.4 |
C5—C4—C3 | 119.02 (17) | H14A—C14—H14B | 108.0 |
C6—C5—C4 | 120.76 (16) | O7—C15—C16 | 111.09 (16) |
C6—C5—H5 | 119.6 | O7—C15—H15A | 109.4 |
C4—C5—H5 | 119.6 | C16—C15—H15A | 109.4 |
C5—C6—C1 | 119.10 (18) | O7—C15—H15B | 109.4 |
C5—C6—H6 | 120.4 | C16—C15—H15B | 109.4 |
C1—C6—H6 | 120.4 | H15A—C15—H15B | 108.0 |
C12—C7—C8 | 120.62 (16) | N3—C16—C15 | 110.39 (15) |
C12—C7—N2 | 120.17 (18) | N3—C16—H16A | 109.6 |
C8—C7—N2 | 119.19 (18) | C15—C16—H16A | 109.6 |
C9—C8—C7 | 119.44 (17) | N3—C16—H16B | 109.6 |
C9—C8—H8 | 120.3 | C15—C16—H16B | 109.6 |
C7—C8—H8 | 120.3 | H16A—C16—H16B | 108.1 |
C8—C9—C10 | 121.85 (16) | O2—N1—O1 | 121.97 (19) |
C8—C9—H9 | 119.1 | O2—N1—C1 | 118.97 (16) |
C10—C9—H9 | 119.1 | O1—N1—C1 | 119.05 (19) |
O6—C10—C9 | 121.87 (15) | O5—N2—O4 | 122.6 (2) |
O6—C10—C11 | 120.85 (15) | O5—N2—C7 | 119.3 (2) |
C9—C10—C11 | 117.26 (15) | O4—N2—C7 | 118.1 (2) |
C12—C11—C10 | 121.06 (17) | C14—O7—C15 | 110.39 (14) |
C12—C11—H11 | 119.5 | C4—O3—H3A | 109.5 |
C10—C11—H11 | 119.5 | C10—O6—H6A | 109.5 |
C11—C12—C7 | 119.76 (16) | C13—N3—C16 | 110.35 (13) |
C11—C12—H12 | 120.1 | C13—N3—H3B | 113.2 (14) |
C7—C12—H12 | 120.1 | C16—N3—H3B | 108.0 (14) |
C6—C1—C2—C3 | −1.0 (3) | C10—C11—C12—C7 | 0.4 (3) |
N1—C1—C2—C3 | 178.82 (18) | C8—C7—C12—C11 | −0.7 (3) |
C1—C2—C3—C4 | 0.8 (3) | N2—C7—C12—C11 | 177.62 (17) |
C2—C3—C4—O3 | −179.62 (18) | N3—C13—C14—O7 | 56.0 (2) |
C2—C3—C4—C5 | −0.2 (3) | O7—C15—C16—N3 | −57.5 (2) |
O3—C4—C5—C6 | 179.03 (19) | C2—C1—N1—O2 | −177.4 (2) |
C3—C4—C5—C6 | −0.4 (3) | C6—C1—N1—O2 | 2.4 (3) |
C4—C5—C6—C1 | 0.3 (3) | C2—C1—N1—O1 | 4.0 (3) |
C2—C1—C6—C5 | 0.4 (3) | C6—C1—N1—O1 | −176.2 (2) |
N1—C1—C6—C5 | −179.37 (18) | C12—C7—N2—O5 | −177.76 (19) |
C12—C7—C8—C9 | 0.1 (3) | C8—C7—N2—O5 | 0.6 (3) |
N2—C7—C8—C9 | −178.17 (17) | C12—C7—N2—O4 | 1.0 (3) |
C7—C8—C9—C10 | 0.6 (3) | C8—C7—N2—O4 | 179.30 (17) |
C8—C9—C10—O6 | −179.63 (17) | C13—C14—O7—C15 | −60.4 (2) |
C8—C9—C10—C11 | −0.8 (3) | C16—C15—O7—C14 | 61.5 (2) |
O6—C10—C11—C12 | 179.10 (16) | C14—C13—N3—C16 | −51.7 (2) |
C9—C10—C11—C12 | 0.3 (3) | C15—C16—N3—C13 | 52.3 (2) |
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···O5iv | 0.97 | 2.49 | 3.403 (3) | 157 |
C15—H15B···O1v | 0.97 | 2.48 | 3.400 (3) | 159 |
C16—H16B···O2vi | 0.97 | 2.56 | 3.441 (3) | 152 |
Symmetry codes: (i) x, y+1, z; (ii) x, −y+3/2, z−1/2; (iii) −x+1, −y+2, −z; (iv) −x, y−3/2, −z+1/2; (v) −x+1, −y, −z; (vi) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | 2C6H5NO3·C4H9NO |
Mr | 365.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 18.0381 (7), 5.5673 (2), 17.4910 (7) |
β (°) | 91.606 (3) |
V (Å3) | 1755.82 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.35 × 0.30 × 0.25 |
Data collection | |
Diffractometer | Bruker SMART APEXII area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.963, 0.973 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16662, 4354, 2987 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.670 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.151, 1.05 |
No. of reflections | 4354 |
No. of parameters | 239 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.45, −0.30 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
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···O5iv | 0.97 | 2.49 | 3.403 (3) | 157 |
C15—H15B···O1v | 0.97 | 2.48 | 3.400 (3) | 159 |
C16—H16B···O2vi | 0.97 | 2.56 | 3.441 (3) | 152 |
Symmetry codes: (i) x, y+1, z; (ii) x, −y+3/2, z−1/2; (iii) −x+1, −y+2, −z; (iv) −x, y−3/2, −z+1/2; (v) −x+1, −y, −z; (vi) −x+1, −y+1, −z. |
Acknowledgements
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.
References
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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.