Morpholine–4-nitro­phenol (1/2)

Muralidharan, S.; Vidyalakshmi, Y.; Srinivasan, T.; Gopalakrishnan, R.; Velmurugan, D.

doi:10.1107/S1600536812047174

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3411

doi:10.1107/S1600536812047174

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Morpholine–4-nitrophenol (1/2)

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

^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

(Received 31 October 2012; accepted 16 November 2012; online 24 November 2012)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.052
wR(F²) = 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

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
Symmetry codes: (i) x, y+1, z; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y+2, -z; (iv) $[-x, y-{\script{3\over 2}}, -z+{\script{1\over 2}}]$ ; (v) -x+1, -y, -z; (vi) -x+1, -y+1, -z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812047174/pv2605sup1.cif

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

checkCIF report

Comment top

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.

Related literature top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: 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).

Figures top

	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.

Morpholine–4-nitrophenol (1/2) top

Crystal data top

2C₆H₅NO₃·C₄H₉NO	F(000) = 768
M_r = 365.34	D_x = 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

Data collection top

Bruker SMART APEXII area-detector diffractometer	4354 independent reflections
Radiation source: fine-focus sealed tube	2987 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and ϕ scans	θ_max = 28.4°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −24→24
T_min = 0.963, T_max = 0.973	k = −7→7
16662 measured reflections	l = −23→22

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)] = 0.052	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(F_o²) + (0.0638P)² + 0.4643P] where P = (F_o² + 2F_c²)/3
4354 reflections	(Δ/σ)_max < 0.001
239 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

2C₆H₅NO₃·C₄H₉NO	V = 1755.82 (12) Å³
M_r = 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)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	4354 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2987 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.973	R_int = 0.027
16662 measured reflections

Refinement top

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	Δρ_max = 0.45 e Å⁻³
4354 reflections	Δρ_min = −0.30 e Å⁻³
239 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

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
M_r	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)
T_min, T_max	0.963, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	16662, 4354, 2987
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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

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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