4-Nitro­phenyl 4-hy­droxy-3-methyl­benzoate

Sreenivasa, S.; Devarajegowda, H.C.; Srinivasa, H.T.; Kumar, V.; Palakshamurthy, B.S.

doi:10.1107/S1600536812048271

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3490

doi:10.1107/S1600536812048271

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4-Nitrophenyl 4-hydroxy-3-methylbenzoate

S. Sreenivasa,^a H. C. Devarajegowda,^b ^* H. T. Srinivasa,^c Vijith Kumar ^d and B. S. Palakshamurthy ^b

^aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur 572 103, Karnataka, India, ^bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, ^cRaman Research Institute, C. V. Raman Avenue, Sadashivanagar, Bangalore 560 080, Karnataka, India, and ^dSoild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 22 November 2012; accepted 25 November 2012; online 30 November 2012)

The asymmetric unit of the title compound, C₁₄H₁₁NO₅, contains two independent molecules in which the dihedral angles between the benzene rings are 89.27 (16) and 77.14 (12)°. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, generating C(8) chains propagating in [010] for one molecule and [001] C(8) chains for the other. The chains are connected by C—H⋯O hydrogen bonds and π–π interactions [shortest centroid–centroid distance = 3.5908 (12)°], generating a three-dimensional network.

Related literature

For general background to aromatic nitro groups, see: Ghosh et al. (2012 ); Sugiyama et al. (2002 ).

Experimental

Crystal data

C₁₄H₁₁NO₅
M_r = 273.24
Monoclinic, C 2/c
a = 42.313 (6) Å
b = 8.0047 (11) Å
c = 16.1078 (18) Å
β = 105.819 (4)°
V = 5249.2 (12) Å³
Z = 16
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.24 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: ψ scan (SADABS; Sheldrick, 2007 ) T_min = 0.975, T_max = 0.983
28460 measured reflections
4602 independent reflections
3349 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.143
S = 1.02
4602 reflections
361 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯O2Aⁱ	0.82	1.94	2.753 (2)	172
O1B—H1B⋯O2Bⁱⁱ	0.82	1.94	2.727 (3)	160
C7B—H7B1⋯O4Aⁱⁱⁱ	0.96	2.50	3.418 (3)	159
C12A—H12A⋯O2Aⁱ	0.93	2.54	3.245 (2)	132
C19B—H19B⋯O5A^iv	0.93	2.58	3.476 (4)	163
Symmetry codes: (i) x, y-1, z; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iv) $[x, -y+2, z-{\script{1\over 2}}]$ .

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: ORTEP-3 (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812048271/hb6999sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812048271/hb6999Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812048271/hb6999Isup3.cml

checkCIF report

Comment top

Electron withdrawing nitro group is an important structural element having good synthetic value in organic synthesis to achieve a wide variety of natural and biological active molecules (Ghosh et al., 2012). Formation of two-component molecular crystals from nitro benzoic acid and aromatic or heterocyclic bases leads to discovery of new functional solid materials for nonlinear optics (Sugiyama et al., 2002).

The asymmetric unit of 4-Nitrophenyl 4-hydroxy-3-methylbenzoate crystallographically two independent molecules are shown in Fig.1. Each independent molecule (a and b) is approximately perpendicular to each other; the dihedral angle is 89.17 (14)°. The dihedral angles between the benzene rings in the two molecules [(C8a–C13a and C15a–C20a) and C8b–C13b and C15b–C20b)] are 89.27 (16)° and 77.14 (12)° respectively. The crystal structure features O—H···O and C—H···O interactions (Table 1) and π—π interactions.

Related literature top

For general background to aromatic nitro groups, see: Ghosh et al. (2012); Sugiyama et al. (2002).

Experimental top

A mixture of 4-nitrophenol (0.100 g, 0.072 mol) and 4-hydroxy-3-methylbenzoic acid (0.109 g, 0.072 mol) and dicyclohexyldicarbodimide (0.150 g, 0.11 mol) in 1 ml of dry dimethylsufoxide (DMSO) was irradiated under microwave (600 MHz) for 5 x 60sec. Reaction was monitored by TLC, after completion of reaction; the reaction mixture was poured into ice cold, dilute hydrochloric acid which precipitated as ester. The crude product was filtered through Buckner funnel with vacuum, washed with water, crude precipitate was stirred for 1 hr with a saturated sodium bicarbonate solution to remove excess acid. The ester was again collected by filtration, washed repeatedly with water, air dried, and then repeatedly crystallized to get colourless plates from an ethanol-chloroform solvent mixture.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The packing of molecules.

4-Nitrophenyl 4-hydroxy-3-methylbenzoate top

Crystal data top

C₁₄H₁₁NO₅	F(000) = 2272
M_r = 273.24	D_x = 1.383 Mg m⁻³
Monoclinic, C2/c	Melting point: 453 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 42.313 (6) Å	Cell parameters from 4602 reflections
b = 8.0047 (11) Å	θ = 2.0–25.1°
c = 16.1078 (18) Å	µ = 0.11 mm⁻¹
β = 105.819 (4)°	T = 298 K
V = 5249.2 (12) Å³	Plate, colourless
Z = 16	0.24 × 0.20 × 0.16 mm

Data collection top

Bruker SMART CCD diffractometer	4602 independent reflections
Radiation source: fine-focus sealed tube	3349 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
ω and ϕ scans	θ_max = 25.1°, θ_min = 2.0°
Absorption correction: ψ scan (SADABS; Sheldrick, 2007)	h = −49→50
T_min = 0.975, T_max = 0.983	k = −9→9
28460 measured reflections	l = −19→19

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0757P)² + 2.2456P] where P = (F_o² + 2F_c²)/3
4602 reflections	(Δ/σ)_max < 0.001
361 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₄H₁₁NO₅	V = 5249.2 (12) Å³
M_r = 273.24	Z = 16
Monoclinic, C2/c	Mo Kα radiation
a = 42.313 (6) Å	µ = 0.11 mm⁻¹
b = 8.0047 (11) Å	T = 298 K
c = 16.1078 (18) Å	0.24 × 0.20 × 0.16 mm
β = 105.819 (4)°

Data collection top

Bruker SMART CCD diffractometer	4602 independent reflections
Absorption correction: ψ scan (SADABS; Sheldrick, 2007)	3349 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.983	R_int = 0.054
28460 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.02	Δρ_max = 0.26 e Å⁻³
4602 reflections	Δρ_min = −0.20 e Å⁻³
361 parameters

Special details top

Experimental. IR (cm^-1); 2923, 2851, 1739, 1603, 1513, 1246, 1199;. 1H-NMR (400 MHz, CDCl₃):8.27 (d, 2H, J = 8.56 Hz, Ar—H), 7.79 (m, 2H, Ar—H), 7.43 (m, 2H, Ar—H), 6.78 (m, 1H, Ar—H), 5.01 (s, 1H, Ar—OH), 2.34 (t, 3H, J = 6.5 Hz, Ar—CH3); Elemental analysis: C₁₄H₁₁NO₅ requires C, 61.54; H, 4.06; N, 5.13; found C, 61.95;H, 4.34; N, 4.79.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1A	−0.03888 (3)	−0.32059 (16)	0.40683 (10)	0.0550 (4)
H1A	−0.0263	−0.3968	0.4036	0.082*
O2A	0.00229 (4)	0.43257 (18)	0.37864 (11)	0.0652 (4)
O3A	0.04796 (3)	0.29667 (16)	0.37629 (10)	0.0542 (4)
O4A	0.12917 (6)	0.9576 (3)	0.45292 (13)	0.1007 (7)
O5A	0.11233 (7)	0.9690 (3)	0.31718 (14)	0.1168 (9)
N6A	0.11378 (5)	0.9012 (2)	0.38481 (14)	0.0611 (5)
C7A	−0.07695 (5)	−0.0418 (3)	0.41356 (16)	0.0605 (6)
H7A1	−0.0824	−0.1574	0.4175	0.091*
H7A2	−0.0930	0.0096	0.3666	0.091*
H7A3	−0.0767	0.0139	0.4665	0.091*
C8A	−0.04364 (5)	−0.0287 (2)	0.39804 (12)	0.0432 (5)
C9A	−0.02951 (5)	0.1231 (2)	0.38957 (12)	0.0446 (5)
H9A	−0.0412	0.2204	0.3921	0.053*
C10A	0.00168 (5)	0.1357 (2)	0.37741 (12)	0.0418 (4)
C11A	0.01863 (5)	−0.0096 (2)	0.37014 (13)	0.0462 (5)
H11A	0.0392	−0.0033	0.3598	0.055*
C12A	0.00513 (5)	−0.1623 (2)	0.37818 (13)	0.0489 (5)
H12A	0.0165	−0.2595	0.3729	0.059*
C13A	−0.02537 (5)	−0.1723 (2)	0.39407 (12)	0.0423 (4)
C14A	0.01605 (5)	0.3012 (2)	0.37702 (12)	0.0440 (5)
C15A	0.06391 (5)	0.4505 (2)	0.37895 (13)	0.0462 (5)
C16A	0.08228 (5)	0.5103 (3)	0.45681 (14)	0.0542 (5)
H16A	0.0835	0.4515	0.5074	0.065*
C17A	0.09898 (5)	0.6592 (3)	0.45916 (13)	0.0526 (5)
H17A	0.1117	0.7023	0.5112	0.063*
C18A	0.09643 (5)	0.7423 (3)	0.38305 (13)	0.0465 (5)
C19A	0.07829 (5)	0.6819 (3)	0.30503 (13)	0.0530 (5)
H19A	0.0771	0.7404	0.2544	0.064*
C20A	0.06183 (5)	0.5328 (3)	0.30305 (14)	0.0544 (5)
H20A	0.0495	0.4886	0.2509	0.065*
O1B	0.29237 (4)	0.4579 (3)	0.43358 (10)	0.0803 (6)
H1B	0.2789	0.4362	0.4602	0.120*
O2B	0.24794 (5)	0.5330 (3)	0.02839 (11)	0.1045 (8)
O3B	0.20070 (4)	0.4732 (2)	0.05604 (9)	0.0719 (5)
O4B	0.13548 (7)	0.4123 (4)	−0.33906 (14)	0.1226 (9)
O5B	0.11288 (6)	0.6376 (3)	−0.31360 (14)	0.1102 (8)
N6B	0.13174 (6)	0.5217 (3)	−0.29087 (14)	0.0750 (6)
C7B	0.33294 (6)	0.5292 (5)	0.33073 (18)	0.0921 (10)
H7B1	0.3386	0.5163	0.3923	0.138*
H7B2	0.3383	0.6403	0.3168	0.138*
H7B3	0.3450	0.4497	0.3068	0.138*
C8B	0.29669 (5)	0.4997 (3)	0.29354 (13)	0.0557 (6)
C9B	0.28152 (5)	0.5074 (3)	0.20657 (14)	0.0582 (6)
H9B	0.2942	0.5300	0.1689	0.070*
C10B	0.24797 (5)	0.4827 (3)	0.17292 (13)	0.0515 (5)
C11B	0.22927 (6)	0.4457 (3)	0.22887 (14)	0.0628 (6)
H11B	0.2068	0.4271	0.2075	0.075*
C12B	0.24386 (6)	0.4367 (4)	0.31560 (14)	0.0663 (7)
H12B	0.2312	0.4119	0.3531	0.080*
C13B	0.27708 (5)	0.4640 (3)	0.34785 (13)	0.0553 (5)
C14B	0.23353 (6)	0.4987 (3)	0.08041 (14)	0.0615 (6)
C15B	0.18461 (5)	0.4871 (3)	−0.03191 (14)	0.0592 (6)
C16B	0.18584 (6)	0.3559 (3)	−0.08597 (16)	0.0668 (6)
H16B	0.1981	0.2609	−0.0650	0.080*
C17B	0.16863 (6)	0.3677 (3)	−0.17177 (15)	0.0654 (6)
H17B	0.1693	0.2816	−0.2100	0.078*
C18B	0.15043 (6)	0.5094 (3)	−0.19964 (14)	0.0591 (6)
C19B	0.14870 (6)	0.6388 (3)	−0.14563 (16)	0.0646 (6)
H19B	0.1360	0.7325	−0.1661	0.077*
C20B	0.16627 (6)	0.6272 (3)	−0.06012 (15)	0.0647 (6)
H20B	0.1657	0.7136	−0.0220	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0550 (9)	0.0383 (7)	0.0738 (10)	−0.0022 (6)	0.0213 (8)	0.0009 (6)
O2A	0.0512 (9)	0.0370 (8)	0.1076 (13)	0.0056 (7)	0.0219 (9)	0.0054 (8)
O3A	0.0462 (8)	0.0380 (7)	0.0792 (10)	−0.0012 (6)	0.0183 (7)	0.0010 (7)
O4A	0.1216 (18)	0.0931 (14)	0.0767 (13)	−0.0565 (13)	0.0087 (12)	−0.0182 (11)
O5A	0.167 (2)	0.0962 (16)	0.0801 (14)	−0.0701 (16)	0.0215 (15)	0.0111 (11)
N6A	0.0621 (12)	0.0575 (11)	0.0652 (13)	−0.0157 (9)	0.0198 (10)	−0.0026 (10)
C7A	0.0465 (12)	0.0540 (13)	0.0842 (16)	−0.0002 (10)	0.0234 (12)	−0.0030 (11)
C8A	0.0384 (11)	0.0444 (11)	0.0441 (11)	0.0027 (8)	0.0068 (9)	−0.0019 (8)
C9A	0.0422 (11)	0.0360 (10)	0.0531 (12)	0.0072 (8)	0.0089 (9)	−0.0016 (8)
C10A	0.0418 (11)	0.0379 (10)	0.0429 (11)	0.0038 (8)	0.0068 (9)	0.0014 (8)
C11A	0.0419 (11)	0.0412 (11)	0.0563 (12)	0.0032 (8)	0.0149 (10)	−0.0017 (9)
C12A	0.0483 (12)	0.0353 (10)	0.0647 (13)	0.0063 (8)	0.0183 (10)	−0.0025 (9)
C13A	0.0448 (11)	0.0379 (10)	0.0403 (10)	−0.0009 (8)	0.0050 (9)	−0.0016 (8)
C14A	0.0408 (11)	0.0393 (10)	0.0486 (12)	0.0047 (9)	0.0069 (9)	0.0028 (8)
C15A	0.0390 (11)	0.0406 (10)	0.0591 (13)	−0.0001 (8)	0.0134 (10)	0.0009 (9)
C16A	0.0580 (13)	0.0565 (13)	0.0459 (12)	−0.0025 (10)	0.0105 (11)	0.0070 (10)
C17A	0.0548 (13)	0.0571 (13)	0.0420 (11)	−0.0066 (10)	0.0064 (10)	−0.0048 (9)
C18A	0.0410 (11)	0.0476 (11)	0.0508 (12)	−0.0037 (9)	0.0120 (9)	−0.0037 (9)
C19A	0.0543 (13)	0.0583 (13)	0.0443 (12)	−0.0088 (10)	0.0100 (10)	0.0053 (9)
C20A	0.0507 (13)	0.0594 (13)	0.0470 (12)	−0.0101 (10)	0.0029 (10)	−0.0025 (10)
O1B	0.0576 (10)	0.1384 (17)	0.0412 (9)	0.0057 (10)	0.0071 (8)	0.0077 (9)
O2B	0.0605 (11)	0.207 (3)	0.0457 (10)	−0.0223 (13)	0.0144 (9)	0.0125 (12)
O3B	0.0469 (9)	0.1225 (15)	0.0421 (9)	−0.0040 (9)	0.0049 (7)	0.0036 (9)
O4B	0.135 (2)	0.151 (2)	0.0596 (13)	0.0139 (17)	−0.0116 (13)	−0.0215 (14)
O5B	0.1202 (18)	0.1087 (17)	0.0772 (14)	0.0137 (15)	−0.0145 (13)	0.0291 (12)
N6B	0.0712 (15)	0.0898 (17)	0.0529 (13)	−0.0161 (13)	−0.0015 (11)	0.0063 (12)
C7B	0.0491 (15)	0.161 (3)	0.0627 (16)	−0.0108 (17)	0.0101 (12)	0.0000 (17)
C8B	0.0443 (12)	0.0739 (15)	0.0475 (12)	0.0047 (10)	0.0105 (10)	−0.0010 (10)
C9B	0.0485 (13)	0.0830 (16)	0.0463 (12)	0.0003 (11)	0.0183 (11)	0.0036 (11)
C10B	0.0441 (12)	0.0677 (14)	0.0423 (11)	0.0020 (10)	0.0114 (9)	−0.0009 (10)
C11B	0.0436 (12)	0.0952 (18)	0.0487 (13)	−0.0038 (12)	0.0112 (10)	0.0032 (12)
C12B	0.0507 (14)	0.1058 (19)	0.0449 (13)	−0.0032 (13)	0.0173 (11)	0.0041 (12)
C13B	0.0486 (13)	0.0741 (15)	0.0409 (12)	0.0076 (11)	0.0083 (10)	0.0022 (10)
C14B	0.0481 (13)	0.0926 (18)	0.0444 (12)	−0.0005 (12)	0.0137 (11)	−0.0012 (11)
C15B	0.0446 (12)	0.0875 (17)	0.0426 (12)	−0.0035 (11)	0.0069 (10)	0.0025 (11)
C16B	0.0604 (15)	0.0727 (16)	0.0593 (15)	0.0090 (12)	0.0022 (12)	0.0038 (12)
C17B	0.0601 (14)	0.0746 (16)	0.0561 (14)	−0.0014 (12)	0.0067 (12)	−0.0092 (12)
C18B	0.0507 (13)	0.0717 (15)	0.0484 (13)	−0.0107 (11)	0.0023 (11)	0.0071 (11)
C19B	0.0586 (14)	0.0637 (14)	0.0648 (16)	0.0007 (11)	0.0056 (12)	0.0063 (12)
C20B	0.0606 (15)	0.0724 (16)	0.0572 (15)	−0.0012 (12)	0.0097 (12)	−0.0074 (12)

Geometric parameters (Å, º) top

O1A—C13A	1.357 (2)	O1B—C13B	1.357 (3)
O1A—H1A	0.8200	O1B—H1B	0.8200
O2A—C14A	1.205 (2)	O2B—C14B	1.195 (3)
O3A—C14A	1.354 (2)	O3B—C14B	1.352 (3)
O3A—C15A	1.399 (2)	O3B—C15B	1.399 (3)
O4A—N6A	1.201 (3)	O4B—N6B	1.209 (3)
O5A—N6A	1.204 (3)	O5B—N6B	1.214 (3)
N6A—C18A	1.465 (3)	N6B—C18B	1.470 (3)
C7A—C8A	1.501 (3)	C7B—C8B	1.505 (3)
C7A—H7A1	0.9600	C7B—H7B1	0.9600
C7A—H7A2	0.9600	C7B—H7B2	0.9600
C7A—H7A3	0.9600	C7B—H7B3	0.9600
C8A—C9A	1.377 (3)	C8B—C9B	1.374 (3)
C8A—C13A	1.396 (3)	C8B—C13B	1.390 (3)
C9A—C10A	1.390 (3)	C9B—C10B	1.389 (3)
C9A—H9A	0.9300	C9B—H9B	0.9300
C10A—C11A	1.388 (3)	C10B—C11B	1.384 (3)
C10A—C14A	1.459 (3)	C10B—C14B	1.454 (3)
C11A—C12A	1.371 (3)	C11B—C12B	1.367 (3)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.385 (3)	C12B—C13B	1.377 (3)
C12A—H12A	0.9300	C12B—H12B	0.9300
C15A—C16A	1.369 (3)	C15B—C20B	1.369 (3)
C15A—C20A	1.370 (3)	C15B—C16B	1.374 (3)
C16A—C17A	1.381 (3)	C16B—C17B	1.378 (3)
C16A—H16A	0.9300	C16B—H16B	0.9300
C17A—C18A	1.373 (3)	C17B—C18B	1.376 (3)
C17A—H17A	0.9300	C17B—H17B	0.9300
C18A—C19A	1.370 (3)	C18B—C19B	1.367 (3)
C19A—C20A	1.378 (3)	C19B—C20B	1.379 (3)
C19A—H19A	0.9300	C19B—H19B	0.9300
C20A—H20A	0.9300	C20B—H20B	0.9300

C13A—O1A—H1A	109.5	C13B—O1B—H1B	109.5
C14A—O3A—C15A	116.73 (15)	C14B—O3B—C15B	117.38 (17)
O4A—N6A—O5A	122.6 (2)	O4B—N6B—O5B	123.4 (2)
O4A—N6A—C18A	119.2 (2)	O4B—N6B—C18B	117.7 (3)
O5A—N6A—C18A	118.2 (2)	O5B—N6B—C18B	118.9 (2)
C8A—C7A—H7A1	109.5	C8B—C7B—H7B1	109.5
C8A—C7A—H7A2	109.5	C8B—C7B—H7B2	109.5
H7A1—C7A—H7A2	109.5	H7B1—C7B—H7B2	109.5
C8A—C7A—H7A3	109.5	C8B—C7B—H7B3	109.5
H7A1—C7A—H7A3	109.5	H7B1—C7B—H7B3	109.5
H7A2—C7A—H7A3	109.5	H7B2—C7B—H7B3	109.5
C9A—C8A—C13A	117.47 (17)	C9B—C8B—C13B	117.3 (2)
C9A—C8A—C7A	122.07 (17)	C9B—C8B—C7B	122.7 (2)
C13A—C8A—C7A	120.43 (17)	C13B—C8B—C7B	120.0 (2)
C8A—C9A—C10A	122.14 (17)	C8B—C9B—C10B	122.36 (19)
C8A—C9A—H9A	118.9	C8B—C9B—H9B	118.8
C10A—C9A—H9A	118.9	C10B—C9B—H9B	118.8
C11A—C10A—C9A	118.95 (17)	C11B—C10B—C9B	118.8 (2)
C11A—C10A—C14A	122.36 (17)	C11B—C10B—C14B	122.1 (2)
C9A—C10A—C14A	118.62 (16)	C9B—C10B—C14B	119.12 (19)
C12A—C11A—C10A	120.06 (18)	C12B—C11B—C10B	119.9 (2)
C12A—C11A—H11A	120.0	C12B—C11B—H11B	120.1
C10A—C11A—H11A	120.0	C10B—C11B—H11B	120.1
C11A—C12A—C13A	120.17 (17)	C11B—C12B—C13B	120.5 (2)
C11A—C12A—H12A	119.9	C11B—C12B—H12B	119.8
C13A—C12A—H12A	119.9	C13B—C12B—H12B	119.8
O1A—C13A—C12A	122.05 (17)	O1B—C13B—C12B	122.19 (19)
O1A—C13A—C8A	116.87 (17)	O1B—C13B—C8B	116.57 (19)
C12A—C13A—C8A	121.08 (17)	C12B—C13B—C8B	121.2 (2)
O2A—C14A—O3A	120.82 (17)	O2B—C14B—O3B	120.8 (2)
O2A—C14A—C10A	126.02 (18)	O2B—C14B—C10B	125.9 (2)
O3A—C14A—C10A	113.15 (16)	O3B—C14B—C10B	113.31 (18)
C16A—C15A—C20A	122.09 (19)	C20B—C15B—C16B	122.1 (2)
C16A—C15A—O3A	118.98 (18)	C20B—C15B—O3B	118.5 (2)
C20A—C15A—O3A	118.86 (19)	C16B—C15B—O3B	119.3 (2)
C15A—C16A—C17A	119.05 (19)	C15B—C16B—C17B	118.8 (2)
C15A—C16A—H16A	120.5	C15B—C16B—H16B	120.6
C17A—C16A—H16A	120.5	C17B—C16B—H16B	120.6
C18A—C17A—C16A	118.60 (19)	C18B—C17B—C16B	118.6 (2)
C18A—C17A—H17A	120.7	C18B—C17B—H17B	120.7
C16A—C17A—H17A	120.7	C16B—C17B—H17B	120.7
C19A—C18A—C17A	122.41 (19)	C19B—C18B—C17B	122.6 (2)
C19A—C18A—N6A	118.49 (18)	C19B—C18B—N6B	118.6 (2)
C17A—C18A—N6A	119.10 (19)	C17B—C18B—N6B	118.8 (2)
C18A—C19A—C20A	118.71 (19)	C18B—C19B—C20B	118.5 (2)
C18A—C19A—H19A	120.6	C18B—C19B—H19B	120.8
C20A—C19A—H19A	120.6	C20B—C19B—H19B	120.8
C15A—C20A—C19A	119.1 (2)	C15B—C20B—C19B	119.3 (2)
C15A—C20A—H20A	120.4	C15B—C20B—H20B	120.4
C19A—C20A—H20A	120.4	C19B—C20B—H20B	120.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2Aⁱ	0.82	1.94	2.753 (2)	172
O1B—H1B···O2Bⁱⁱ	0.82	1.94	2.727 (3)	160
C7B—H7B1···O4Aⁱⁱⁱ	0.96	2.50	3.418 (3)	159
C12A—H12A···O2Aⁱ	0.93	2.54	3.245 (2)	132
C19B—H19B···O5A^iv	0.93	2.58	3.476 (4)	163

Symmetry codes: (i) x, y−1, z; (ii) x, −y+1, z+1/2; (iii) −x+1/2, −y+3/2, −z+1; (iv) x, −y+2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁NO₅
M_r	273.24
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	42.313 (6), 8.0047 (11), 16.1078 (18)
β (°)	105.819 (4)
V (Å³)	5249.2 (12)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.24 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	ψ scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.975, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	28460, 4602, 3349
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.143, 1.02
No. of reflections	4602
No. of parameters	361
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.20

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2Aⁱ	0.82	1.94	2.753 (2)	172
O1B—H1B···O2Bⁱⁱ	0.82	1.94	2.727 (3)	160
C7B—H7B1···O4Aⁱⁱⁱ	0.96	2.50	3.418 (3)	159
C12A—H12A···O2Aⁱ	0.93	2.54	3.245 (2)	132
C19B—H19B···O5A^iv	0.93	2.58	3.476 (4)	163

Symmetry codes: (i) x, y−1, z; (ii) x, −y+1, z+1/2; (iii) −x+1/2, −y+3/2, −z+1; (iv) x, −y+2, z−1/2.

Acknowledgements

The authors thank Professor T. N. Guru Row, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, and G. B. Sadananda, Department of Studies and Research in Physics, U.C.S. Tumkur University, Tumkur for their help and suggestions.

References

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Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ghosh, P. P., Pal, G., Paul, S. & Das, A. R. (2012). Green Chem. 14, 2691–2698. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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