N-[(2-Hydr­oxy-1-naphthyl)(3-nitro­phenyl)meth­yl]acetamide

NizamMohideen, M.; SubbiahPandi, A.; Panneer Selvam, N.; Perumal, P.T.

doi:10.1107/S1600536809007442

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages o714-o715

doi:10.1107/S1600536809007442

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N-[(2-Hydroxy-1-naphthyl)(3-nitrophenyl)methyl]acetamide

M. NizamMohideen,^a A. SubbiahPandi,^b ^* N. Panneer Selvam ^c and P. T. Perumal ^c

^aDepartment of Physics, The New College (Autonomous), Chennai 600 014, India, ^bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^cOrganic Chemistry Division, Central Leather Research Institute, Chennai 600 020, India
^*Correspondence e-mail: a_spandian@yahoo.com

(Received 9 January 2009; accepted 28 February 2009; online 6 March 2009)

The title compound, C₁₉H₁₆N₂O₄, is of interest as a precursor to biologically active substituted quinolines and related compounds. The dihedral angle between the naphthalene ring system and the benzene ring is 81.9 (1)°. The crystal structure is stabilized by N—H⋯O intermolecular hydrogen bonds, linking the molecules into pairs around a center of symmetry. The crystal structure is further stabilized by intermolecular O—H⋯O hydrogen bonds, which link the molecules into chains running along a axis. An intramolecular C—H⋯O short contact is also present.

Related literature

For N-(substituted phenyl)acetamides as precursors for the synthesis of hetrocyclic compounds, see: Wen et al. (2005 , 2006 ). For multicomponent reactions, see: Devi & Bhuyan (2004 ); Domling & Ugi (2000 ). For the properties and potential applications of amide-type compounds and their metal ion complexes, see: Saravanakumar et al. (2005 ); Yin et al. (2004 ). For related structures, see: Mosslemin et al. (2007 ); Zia-ur-Rehman et al. (2008 ). For bond-length data, see: Allen et al. (1987 ); Liu & Li (2004 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₉H₁₆N₂O₄
M_r = 336.34
Triclinic, $[P \overline 1]$
a = 7.5261 (4) Å
b = 8.8635 (5) Å
c = 13.3008 (7) Å
α = 74.720 (3)°
β = 73.754 (3)°
γ = 82.600 (3)°
V = 820.27 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.4 × 0.2 × 0.1 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.974, T_max = 0.990
9406 measured reflections
3864 independent reflections
2227 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.144
S = 0.99
3864 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4ⁱ	0.82	1.87	2.646 (2)	158
N1—H1A⋯O2ⁱⁱ	0.86	2.35	3.167 (2)	160
C11—H11⋯O4	0.98	2.28	2.739 (2)	107
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009)'.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007442/jh2076sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809007442/jh2076Isup2.hkl

checkCIF report

Comment top

N-(substituted phenyl)acetamides are well known for their importance as intermediates in organic synthesis. They are used as precursors for the synthesis of many hetrocyclic compounds (Wen et al., 2005, 2006). Multi-component reactions (MCRs) have attracted considerable attention in terms of the saving of both energy and raw materials (Devi & Bhuyan, 2004). They have merits over multi-step reactions in several aspects, including the simplicity of a one-pot procedure, possible structural variations and in building up complex molecules (Domling & Ugi, 2000). Much attention has been focused on amide-type compounds and their metal ion complexes for their properties and potential applications including molecular recognition, ion electrodes, photochemistry and topological structures in ion extraction, biochemistry, catalysis and magnetism (Saravanakumar et al., 2005; Yin et al., 2004). The amide linkage [–NHC(O)-] is known to be strong enough to form and maintain protein architectures and has been utilized to create various molecular devices for a spectrum of purposes in organic chemistry. In order to obtain fundamental information about this phenomenon, an X-ray crystal structure analysis of (I) was undertaken.

The conformation of (I), together with the atom-numbering scheme, is shown in Fig. 1. In the structure, all bond lengths and angles are within normal ranges (Allen et al., 1987), and comparable with those in previously reported structure (Mosslemin et al., 2007). The bond distance of C18=O4 is 1.222 (2) Å, which is typical for double bonds (Liu & Li., 2004). The nitro group is slighty twisted out of the plane of the benzene ring, as indicated by O2—N2—C16—C15 and O3—N2—C16—C15 torsion angles of -162.9 (2) and 14.4 (3)°, respectively, and comparable with those in previously reported structure (Zia-ur-Rehman et al., 2008).

The naphthalene ring is planar, the maximum deviation from the least squares plane being -0.027 (1) Å for atom C7. Atom O1 deviating by 0.05 (1) Å from the least squares plane of the naphthalene ring. The dihedral angle between the naphthalene and benzene ring is 81.9 (1)°. The dihedral angle between the fused rings is 1.1 (1)°.

The crystal structure is stabilized by N—H···O intermolecular hydrogen bonds (Table 1, Fig 2.) that generate centrosymmetric hydrogenbonded dimers with a cyclic R²₂(16) ring system (Bernstein, et al., 1995). The crystal structure is further stabilized by intermolecular O—H···O hydrogen bonds link the molecules into chains running along a axis.

Related literature top

For N-(substituted phenyl)acetamides as precursors for the synthesis of hetrocyclic compounds, see: Wen et al. (2005, 2006). For multi-component reactions, see: Devi & Bhuyan (2004); Domling & Ugi (2000). For the properties and potential applications of amide-type compounds and their metal ion complexes, see: Saravanakumar et al. (2005); Yin et al. (2004). For related structures, see: Mosslemin et al. (2007); Zia-ur-Rehman et al. (2008). For bond-length data, see: Allen et al. (1987); Liu & Li (2004). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of 3-nitrobenzaldehyde (10 mmol), β-naphthol (10 mmol) and iodine (0.4 mmol, 4 mol%) were mixed in acetonitrile (5 ml). To that suspension acetyl chloride (2.8 mmol, 0.2 ml) was added and the reaction mixture was stirred at room temperature for 3 h. After the completion of the reaction (as monitored by TLC), saturated sodium thiosulfate solution (5 ml) was added. The precipitated solid was filtered and dried. The dried sample was washed with diethyl ether (2 x 10 ml) and again dried. Single crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a solution in Ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: 'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'.

Figures top

	Fig. 1. The molecular configuration and atom-numbering scheme for (I). Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure of (I), showing the R²₂(16) rings. For the sake of clarity, H atoms not participating in the hydrogen bonding have been omitted. Hydrogen bonding is shown as dashed lines. [Symmetry codes: (*) -x + 2, -y + 1, -z + 1]

N-[(2-Hydroxy-1-naphthyl)(3-nitrophenyl)methyl]acetamide top

Crystal data top

C₁₉H₁₆N₂O₄	Z = 2
M_r = 336.34	F(000) = 352
Triclinic, P1	D_x = 1.362 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5261 (4) Å	Cell parameters from 3864 reflections
b = 8.8635 (5) Å	θ = 2.5–25°
c = 13.3008 (7) Å	µ = 0.10 mm⁻¹
α = 74.720 (3)°	T = 293 K
β = 73.754 (3)°	Needle, colourless
γ = 82.600 (3)°	0.4 × 0.2 × 0.1 mm
V = 820.27 (14) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	3864 independent reflections
Radiation source: fine-focus sealed tube	2227 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω and ϕ scan	θ_max = 28.4°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→10
T_min = 0.974, T_max = 0.990	k = −11→11
9406 measured reflections	l = −17→17

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0612P)² + 0.220P] where P = (F_o² + 2F_c²)/3
3864 reflections	(Δ/σ)_max = 0.009
227 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₉H₁₆N₂O₄	γ = 82.600 (3)°
M_r = 336.34	V = 820.27 (14) Å³
Triclinic, P1	Z = 2
a = 7.5261 (4) Å	Mo Kα radiation
b = 8.8635 (5) Å	µ = 0.10 mm⁻¹
c = 13.3008 (7) Å	T = 293 K
α = 74.720 (3)°	0.4 × 0.2 × 0.1 mm
β = 73.754 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3864 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2227 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.990	R_int = 0.026
9406 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 0.99	Δρ_max = 0.21 e Å⁻³
3864 reflections	Δρ_min = −0.17 e Å⁻³
227 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
O1	1.11375 (16)	0.78003 (16)	0.26550 (11)	0.0490 (4)
H1	1.2259	0.7587	0.2525	0.074*
O2	0.9758 (4)	0.5649 (2)	0.62604 (17)	0.1025 (7)
O3	0.8781 (4)	0.6954 (3)	0.74538 (16)	0.1150 (8)
O4	0.46636 (19)	0.7392 (2)	0.26984 (17)	0.0801 (6)
N1	0.74868 (19)	0.71417 (18)	0.29573 (12)	0.0401 (4)
H1A	0.8443	0.6528	0.3045	0.048*
N2	0.8965 (3)	0.6794 (3)	0.65559 (16)	0.0667 (5)
C1	1.0777 (2)	0.9135 (2)	0.19395 (14)	0.0385 (4)
C2	1.2195 (2)	0.9945 (3)	0.11175 (16)	0.0502 (5)
H2	1.3425	0.9575	0.1056	0.060*
C3	1.1769 (3)	1.1262 (3)	0.04174 (17)	0.0536 (5)
H3	1.2720	1.1793	−0.0117	0.064*
C4	0.9922 (3)	1.1848 (2)	0.04788 (15)	0.0473 (5)
C5	0.9457 (4)	1.3208 (3)	−0.02594 (17)	0.0632 (6)
H5	1.0402	1.3758	−0.0786	0.076*
C6	0.7679 (4)	1.3729 (3)	−0.0220 (2)	0.0732 (7)
H6	0.7408	1.4619	−0.0721	0.088*
C7	0.6253 (4)	1.2929 (3)	0.05736 (19)	0.0634 (6)
H7	0.5029	1.3285	0.0595	0.076*
C8	0.6626 (3)	1.1628 (2)	0.13215 (17)	0.0495 (5)
H8	0.5649	1.1126	0.1852	0.059*
C9	0.8474 (2)	1.1027 (2)	0.13058 (14)	0.0384 (4)
C10	0.8943 (2)	0.9665 (2)	0.20492 (14)	0.0353 (4)
C11	0.7483 (2)	0.8774 (2)	0.29803 (14)	0.0356 (4)
H11	0.6276	0.9264	0.2889	0.043*
C12	0.7637 (2)	0.8970 (2)	0.40573 (14)	0.0366 (4)
C13	0.7214 (2)	1.0446 (2)	0.42690 (16)	0.0448 (5)
H13	0.6865	1.1272	0.3751	0.054*
C14	0.7299 (3)	1.0718 (3)	0.52306 (17)	0.0508 (5)
H14	0.6998	1.1715	0.5356	0.061*
C15	0.7827 (3)	0.9515 (3)	0.60021 (16)	0.0500 (5)
H15	0.7880	0.9677	0.6656	0.060*
C16	0.8275 (3)	0.8069 (2)	0.57761 (15)	0.0452 (5)
C17	0.8192 (2)	0.7764 (2)	0.48202 (14)	0.0411 (4)
H17	0.8504	0.6766	0.4697	0.049*
C18	0.6061 (2)	0.6567 (2)	0.28056 (16)	0.0457 (5)
C19	0.6235 (3)	0.4876 (3)	0.2787 (2)	0.0719 (7)
H19A	0.5450	0.4293	0.3438	0.108*
H19B	0.7499	0.4483	0.2734	0.108*
H19C	0.5866	0.4764	0.2176	0.108*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0284 (6)	0.0571 (9)	0.0628 (9)	0.0062 (6)	−0.0192 (6)	−0.0126 (7)
O2	0.163 (2)	0.0682 (13)	0.0971 (15)	0.0310 (13)	−0.0825 (15)	−0.0215 (12)
O3	0.189 (3)	0.1062 (17)	0.0557 (12)	0.0012 (16)	−0.0525 (14)	−0.0122 (11)
O4	0.0403 (8)	0.0771 (12)	0.1474 (17)	0.0087 (8)	−0.0497 (10)	−0.0471 (12)
N1	0.0309 (7)	0.0380 (9)	0.0574 (9)	0.0045 (6)	−0.0211 (7)	−0.0146 (7)
N2	0.0861 (14)	0.0639 (14)	0.0559 (12)	−0.0130 (11)	−0.0321 (10)	−0.0056 (11)
C1	0.0318 (8)	0.0457 (11)	0.0440 (10)	0.0000 (8)	−0.0138 (7)	−0.0177 (9)
C2	0.0313 (9)	0.0701 (14)	0.0556 (12)	−0.0066 (9)	−0.0079 (8)	−0.0277 (11)
C3	0.0516 (12)	0.0623 (14)	0.0462 (11)	−0.0172 (10)	−0.0023 (9)	−0.0161 (11)
C4	0.0581 (12)	0.0454 (12)	0.0416 (10)	−0.0068 (9)	−0.0100 (9)	−0.0170 (9)
C5	0.0878 (18)	0.0488 (13)	0.0467 (12)	−0.0081 (12)	−0.0087 (12)	−0.0080 (11)
C6	0.104 (2)	0.0478 (14)	0.0603 (15)	0.0171 (14)	−0.0250 (14)	−0.0070 (12)
C7	0.0736 (15)	0.0513 (13)	0.0669 (15)	0.0205 (12)	−0.0295 (12)	−0.0161 (12)
C8	0.0502 (11)	0.0455 (12)	0.0554 (12)	0.0086 (9)	−0.0204 (9)	−0.0145 (10)
C9	0.0424 (9)	0.0368 (10)	0.0410 (10)	0.0010 (8)	−0.0135 (8)	−0.0162 (8)
C10	0.0314 (8)	0.0386 (10)	0.0418 (10)	−0.0003 (7)	−0.0128 (7)	−0.0165 (8)
C11	0.0268 (8)	0.0343 (10)	0.0496 (10)	0.0039 (7)	−0.0154 (7)	−0.0131 (8)
C12	0.0238 (7)	0.0404 (10)	0.0462 (10)	−0.0016 (7)	−0.0079 (7)	−0.0126 (8)
C13	0.0374 (9)	0.0424 (11)	0.0554 (12)	0.0021 (8)	−0.0107 (8)	−0.0162 (9)
C14	0.0437 (10)	0.0500 (12)	0.0622 (13)	−0.0030 (9)	−0.0055 (9)	−0.0280 (11)
C15	0.0436 (10)	0.0636 (14)	0.0466 (11)	−0.0122 (10)	−0.0046 (9)	−0.0229 (11)
C16	0.0413 (10)	0.0504 (12)	0.0440 (11)	−0.0097 (9)	−0.0106 (8)	−0.0084 (9)
C17	0.0389 (9)	0.0405 (11)	0.0468 (11)	−0.0037 (8)	−0.0121 (8)	−0.0133 (9)
C18	0.0350 (9)	0.0511 (12)	0.0568 (12)	−0.0047 (8)	−0.0161 (8)	−0.0175 (10)
C19	0.0677 (15)	0.0586 (15)	0.103 (2)	−0.0135 (12)	−0.0270 (14)	−0.0323 (15)

Geometric parameters (Å, º) top

O1—C1	1.359 (2)	C7—H7	0.9300
O1—H1	0.8200	C8—C9	1.420 (3)
O2—N2	1.209 (3)	C8—H8	0.9300
O3—N2	1.207 (3)	C9—C10	1.420 (2)
O4—C18	1.222 (2)	C10—C11	1.520 (2)
N1—C18	1.329 (2)	C11—C12	1.525 (2)
N1—C11	1.455 (2)	C11—H11	0.9800
N1—H1A	0.8600	C12—C17	1.378 (2)
N2—C16	1.468 (3)	C12—C13	1.389 (3)
C1—C10	1.380 (2)	C13—C14	1.382 (3)
C1—C2	1.407 (3)	C13—H13	0.9300
C2—C3	1.353 (3)	C14—C15	1.375 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.408 (3)	C15—C16	1.372 (3)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.414 (3)	C16—C17	1.387 (3)
C4—C9	1.428 (3)	C17—H17	0.9300
C5—C6	1.349 (3)	C18—O4	1.222 (2)
C5—H5	0.9300	C18—C19	1.494 (3)
C6—C7	1.391 (4)	C19—H19A	0.9600
C6—H6	0.9300	C19—H19B	0.9600
C7—C8	1.366 (3)	C19—H19C	0.9600

C1—O1—H1	109.5	C9—C10—C11	121.98 (14)
C18—N1—C11	122.19 (15)	N1—C11—C10	112.60 (14)
C18—N1—H1A	118.9	N1—C11—C12	112.92 (14)
C11—N1—H1A	118.9	C10—C11—C12	111.04 (13)
O3—N2—O2	122.6 (2)	N1—C11—H11	106.6
O3—N2—C16	118.8 (2)	C10—C11—H11	106.6
O2—N2—C16	118.6 (2)	C12—C11—H11	106.6
O1—C1—C10	116.89 (16)	C17—C12—C13	118.70 (17)
O1—C1—C2	122.07 (15)	C17—C12—C11	123.28 (16)
C10—C1—C2	121.03 (17)	C13—C12—C11	118.02 (16)
C3—C2—C1	120.01 (18)	C14—C13—C12	121.61 (19)
C3—C2—H2	120.0	C14—C13—H13	119.2
C1—C2—H2	120.0	C12—C13—H13	119.2
C2—C3—C4	121.59 (19)	C15—C14—C13	120.02 (19)
C2—C3—H3	119.2	C15—C14—H14	120.0
C4—C3—H3	119.2	C13—C14—H14	120.0
C3—C4—C5	122.1 (2)	C16—C15—C14	117.86 (18)
C3—C4—C9	118.75 (18)	C16—C15—H15	121.1
C5—C4—C9	119.13 (19)	C14—C15—H15	121.1
C6—C5—C4	121.8 (2)	C15—C16—C17	123.22 (19)
C6—C5—H5	119.1	C15—C16—N2	118.79 (18)
C4—C5—H5	119.1	C17—C16—N2	117.91 (19)
C5—C6—C7	119.7 (2)	C12—C17—C16	118.56 (18)
C5—C6—H6	120.2	C12—C17—H17	120.7
C7—C6—H6	120.2	C16—C17—H17	120.7
C8—C7—C6	121.0 (2)	O4—C18—N1	120.94 (18)
C8—C7—H7	119.5	O4—C18—N1	120.94 (18)
C6—C7—H7	119.5	O4—C18—C19	121.76 (18)
C7—C8—C9	121.4 (2)	O4—C18—C19	121.76 (18)
C7—C8—H8	119.3	N1—C18—C19	117.29 (17)
C9—C8—H8	119.3	C18—C19—H19A	109.5
C10—C9—C8	123.85 (17)	C18—C19—H19B	109.5
C10—C9—C4	119.07 (16)	H19A—C19—H19B	109.5
C8—C9—C4	117.07 (17)	C18—C19—H19C	109.5
C1—C10—C9	119.52 (16)	H19A—C19—H19C	109.5
C1—C10—C11	118.50 (15)	H19B—C19—H19C	109.5

O1—C1—C2—C3	179.40 (18)	C1—C10—C11—N1	−58.74 (19)
C10—C1—C2—C3	−0.2 (3)	C9—C10—C11—N1	122.18 (17)
C1—C2—C3—C4	−0.7 (3)	C1—C10—C11—C12	69.00 (19)
C2—C3—C4—C5	−178.9 (2)	C9—C10—C11—C12	−110.08 (17)
C2—C3—C4—C9	0.3 (3)	N1—C11—C12—C17	15.6 (2)
C3—C4—C5—C6	177.5 (2)	C10—C11—C12—C17	−111.95 (18)
C9—C4—C5—C6	−1.7 (3)	N1—C11—C12—C13	−165.13 (14)
C4—C5—C6—C7	0.9 (4)	C10—C11—C12—C13	67.30 (18)
C5—C6—C7—C8	0.6 (4)	C17—C12—C13—C14	−1.4 (3)
C6—C7—C8—C9	−1.2 (3)	C11—C12—C13—C14	179.28 (16)
C7—C8—C9—C10	−178.80 (19)	C12—C13—C14—C15	0.6 (3)
C7—C8—C9—C4	0.4 (3)	C13—C14—C15—C16	0.6 (3)
C3—C4—C9—C10	1.0 (3)	C14—C15—C16—C17	−1.0 (3)
C5—C4—C9—C10	−179.76 (18)	C14—C15—C16—N2	175.85 (18)
C3—C4—C9—C8	−178.19 (18)	O3—N2—C16—C15	14.4 (3)
C5—C4—C9—C8	1.0 (3)	O2—N2—C16—C15	−162.9 (2)
O1—C1—C10—C9	−178.11 (15)	O3—N2—C16—C17	−168.6 (2)
C2—C1—C10—C9	1.5 (3)	O2—N2—C16—C17	14.1 (3)
O1—C1—C10—C11	2.8 (2)	C13—C12—C17—C16	1.1 (2)
C2—C1—C10—C11	−177.60 (16)	C11—C12—C17—C16	−179.69 (16)
C8—C9—C10—C1	177.26 (17)	C15—C16—C17—C12	0.1 (3)
C4—C9—C10—C1	−1.9 (2)	N2—C16—C17—C12	−176.74 (16)
C8—C9—C10—C11	−3.7 (3)	C11—N1—C18—O4	−1.4 (3)
C4—C9—C10—C11	177.17 (16)	C11—N1—C18—O4	−1.4 (3)
C18—N1—C11—C10	−114.89 (18)	C11—N1—C18—C19	179.39 (19)
C18—N1—C11—C12	118.37 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.82	1.87	2.646 (2)	158
N1—H1A···O2ⁱⁱ	0.86	2.35	3.167 (2)	160
C11—H11···O4	0.98	2.28	2.739 (2)	107

Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆N₂O₄
M_r	336.34
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.5261 (4), 8.8635 (5), 13.3008 (7)
α, β, γ (°)	74.720 (3), 73.754 (3), 82.600 (3)
V (Å³)	820.27 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.4 × 0.2 × 0.1

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.974, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	9406, 3864, 2227
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.144, 0.99
No. of reflections	3864
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.17

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), '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
O1—H1···O4ⁱ	0.82	1.87	2.646 (2)	158.0
N1—H1A···O2ⁱⁱ	0.86	2.35	3.167 (2)	160.1
C11—H11···O4	0.98	2.28	2.739 (2)	107.4

Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+1, −z+1.

Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with collecting the X-ray intensity data. MNM and ASP thank Dr J. Jothi Kumar, Principal of Presidency College, Chennai, India, for providing the computer and internet facilities.

References

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