organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

4-Nitro­phenyl 4-hy­dr­oxy-3-methyl­benzoate

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 ππ 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[Ghosh, P. P., Pal, G., Paul, S. & Das, A. R. (2012). Green Chem. 14, 2691-2698.]); Sugiyama et al. (2002[Sugiyama, T., Meng, J., Wen, Z., Li, J. & Matsuura, T. (2002). Mol. Cryst. Liq. Cryst. 389, 17-23.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11NO5

  • Mr = 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[Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.975, Tmax = 0.983

  • 28460 measured reflections

  • 4602 independent reflections

  • 3349 reflections with I > 2σ(I)

  • Rint = 0.054

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.143

  • S = 1.02

  • 4602 reflections

  • 361 parameters

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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⋯O5Aiv 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[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.

Supporting information


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 ππ 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.

Refinement top

All H atoms were positioned geometrically, with O—H = 0.82, C—H = 0.93 Å for aromatic H, and C—H = 0.96 Å for methyl H,and refined using a riding model with Uiso(H) = 1.5Ueq(C) for methyl H and Uiso(H) = 1.2Ueq(C) for all other H.

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
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The packing of molecules.
4-Nitrophenyl 4-hydroxy-3-methylbenzoate top
Crystal data top
C14H11NO5F(000) = 2272
Mr = 273.24Dx = 1.383 Mg m3
Monoclinic, C2/cMelting point: 453 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 42.313 (6) ÅCell parameters from 4602 reflections
b = 8.0047 (11) Åθ = 2.0–25.1°
c = 16.1078 (18) ŵ = 0.11 mm1
β = 105.819 (4)°T = 298 K
V = 5249.2 (12) Å3Plate, colourless
Z = 160.24 × 0.20 × 0.16 mm
Data collection top
Bruker SMART CCD
diffractometer
4602 independent reflections
Radiation source: fine-focus sealed tube3349 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ω and ϕ scansθmax = 25.1°, θmin = 2.0°
Absorption correction: ψ scan
(SADABS; Sheldrick, 2007)
h = 4950
Tmin = 0.975, Tmax = 0.983k = 99
28460 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0757P)2 + 2.2456P]
where P = (Fo2 + 2Fc2)/3
4602 reflections(Δ/σ)max < 0.001
361 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C14H11NO5V = 5249.2 (12) Å3
Mr = 273.24Z = 16
Monoclinic, C2/cMo Kα radiation
a = 42.313 (6) ŵ = 0.11 mm1
b = 8.0047 (11) ÅT = 298 K
c = 16.1078 (18) Å0.24 × 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)
Tmin = 0.975, Tmax = 0.983Rint = 0.054
28460 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.143H-atom parameters constrained
S = 1.02Δρmax = 0.26 e Å3
4602 reflectionsΔρmin = 0.20 e Å3
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
xyzUiso*/Ueq
O1A0.03888 (3)0.32059 (16)0.40683 (10)0.0550 (4)
H1A0.02630.39680.40360.082*
O2A0.00229 (4)0.43257 (18)0.37864 (11)0.0652 (4)
O3A0.04796 (3)0.29667 (16)0.37629 (10)0.0542 (4)
O4A0.12917 (6)0.9576 (3)0.45292 (13)0.1007 (7)
O5A0.11233 (7)0.9690 (3)0.31718 (14)0.1168 (9)
N6A0.11378 (5)0.9012 (2)0.38481 (14)0.0611 (5)
C7A0.07695 (5)0.0418 (3)0.41356 (16)0.0605 (6)
H7A10.08240.15740.41750.091*
H7A20.09300.00960.36660.091*
H7A30.07670.01390.46650.091*
C8A0.04364 (5)0.0287 (2)0.39804 (12)0.0432 (5)
C9A0.02951 (5)0.1231 (2)0.38957 (12)0.0446 (5)
H9A0.04120.22040.39210.053*
C10A0.00168 (5)0.1357 (2)0.37741 (12)0.0418 (4)
C11A0.01863 (5)0.0096 (2)0.37014 (13)0.0462 (5)
H11A0.03920.00330.35980.055*
C12A0.00513 (5)0.1623 (2)0.37818 (13)0.0489 (5)
H12A0.01650.25950.37290.059*
C13A0.02537 (5)0.1723 (2)0.39407 (12)0.0423 (4)
C14A0.01605 (5)0.3012 (2)0.37702 (12)0.0440 (5)
C15A0.06391 (5)0.4505 (2)0.37895 (13)0.0462 (5)
C16A0.08228 (5)0.5103 (3)0.45681 (14)0.0542 (5)
H16A0.08350.45150.50740.065*
C17A0.09898 (5)0.6592 (3)0.45916 (13)0.0526 (5)
H17A0.11170.70230.51120.063*
C18A0.09643 (5)0.7423 (3)0.38305 (13)0.0465 (5)
C19A0.07829 (5)0.6819 (3)0.30503 (13)0.0530 (5)
H19A0.07710.74040.25440.064*
C20A0.06183 (5)0.5328 (3)0.30305 (14)0.0544 (5)
H20A0.04950.48860.25090.065*
O1B0.29237 (4)0.4579 (3)0.43358 (10)0.0803 (6)
H1B0.27890.43620.46020.120*
O2B0.24794 (5)0.5330 (3)0.02839 (11)0.1045 (8)
O3B0.20070 (4)0.4732 (2)0.05604 (9)0.0719 (5)
O4B0.13548 (7)0.4123 (4)0.33906 (14)0.1226 (9)
O5B0.11288 (6)0.6376 (3)0.31360 (14)0.1102 (8)
N6B0.13174 (6)0.5217 (3)0.29087 (14)0.0750 (6)
C7B0.33294 (6)0.5292 (5)0.33073 (18)0.0921 (10)
H7B10.33860.51630.39230.138*
H7B20.33830.64030.31680.138*
H7B30.34500.44970.30680.138*
C8B0.29669 (5)0.4997 (3)0.29354 (13)0.0557 (6)
C9B0.28152 (5)0.5074 (3)0.20657 (14)0.0582 (6)
H9B0.29420.53000.16890.070*
C10B0.24797 (5)0.4827 (3)0.17292 (13)0.0515 (5)
C11B0.22927 (6)0.4457 (3)0.22887 (14)0.0628 (6)
H11B0.20680.42710.20750.075*
C12B0.24386 (6)0.4367 (4)0.31560 (14)0.0663 (7)
H12B0.23120.41190.35310.080*
C13B0.27708 (5)0.4640 (3)0.34785 (13)0.0553 (5)
C14B0.23353 (6)0.4987 (3)0.08041 (14)0.0615 (6)
C15B0.18461 (5)0.4871 (3)0.03191 (14)0.0592 (6)
C16B0.18584 (6)0.3559 (3)0.08597 (16)0.0668 (6)
H16B0.19810.26090.06500.080*
C17B0.16863 (6)0.3677 (3)0.17177 (15)0.0654 (6)
H17B0.16930.28160.21000.078*
C18B0.15043 (6)0.5094 (3)0.19964 (14)0.0591 (6)
C19B0.14870 (6)0.6388 (3)0.14563 (16)0.0646 (6)
H19B0.13600.73250.16610.077*
C20B0.16627 (6)0.6272 (3)0.06012 (15)0.0647 (6)
H20B0.16570.71360.02200.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0550 (9)0.0383 (7)0.0738 (10)0.0022 (6)0.0213 (8)0.0009 (6)
O2A0.0512 (9)0.0370 (8)0.1076 (13)0.0056 (7)0.0219 (9)0.0054 (8)
O3A0.0462 (8)0.0380 (7)0.0792 (10)0.0012 (6)0.0183 (7)0.0010 (7)
O4A0.1216 (18)0.0931 (14)0.0767 (13)0.0565 (13)0.0087 (12)0.0182 (11)
O5A0.167 (2)0.0962 (16)0.0801 (14)0.0701 (16)0.0215 (15)0.0111 (11)
N6A0.0621 (12)0.0575 (11)0.0652 (13)0.0157 (9)0.0198 (10)0.0026 (10)
C7A0.0465 (12)0.0540 (13)0.0842 (16)0.0002 (10)0.0234 (12)0.0030 (11)
C8A0.0384 (11)0.0444 (11)0.0441 (11)0.0027 (8)0.0068 (9)0.0019 (8)
C9A0.0422 (11)0.0360 (10)0.0531 (12)0.0072 (8)0.0089 (9)0.0016 (8)
C10A0.0418 (11)0.0379 (10)0.0429 (11)0.0038 (8)0.0068 (9)0.0014 (8)
C11A0.0419 (11)0.0412 (11)0.0563 (12)0.0032 (8)0.0149 (10)0.0017 (9)
C12A0.0483 (12)0.0353 (10)0.0647 (13)0.0063 (8)0.0183 (10)0.0025 (9)
C13A0.0448 (11)0.0379 (10)0.0403 (10)0.0009 (8)0.0050 (9)0.0016 (8)
C14A0.0408 (11)0.0393 (10)0.0486 (12)0.0047 (9)0.0069 (9)0.0028 (8)
C15A0.0390 (11)0.0406 (10)0.0591 (13)0.0001 (8)0.0134 (10)0.0009 (9)
C16A0.0580 (13)0.0565 (13)0.0459 (12)0.0025 (10)0.0105 (11)0.0070 (10)
C17A0.0548 (13)0.0571 (13)0.0420 (11)0.0066 (10)0.0064 (10)0.0048 (9)
C18A0.0410 (11)0.0476 (11)0.0508 (12)0.0037 (9)0.0120 (9)0.0037 (9)
C19A0.0543 (13)0.0583 (13)0.0443 (12)0.0088 (10)0.0100 (10)0.0053 (9)
C20A0.0507 (13)0.0594 (13)0.0470 (12)0.0101 (10)0.0029 (10)0.0025 (10)
O1B0.0576 (10)0.1384 (17)0.0412 (9)0.0057 (10)0.0071 (8)0.0077 (9)
O2B0.0605 (11)0.207 (3)0.0457 (10)0.0223 (13)0.0144 (9)0.0125 (12)
O3B0.0469 (9)0.1225 (15)0.0421 (9)0.0040 (9)0.0049 (7)0.0036 (9)
O4B0.135 (2)0.151 (2)0.0596 (13)0.0139 (17)0.0116 (13)0.0215 (14)
O5B0.1202 (18)0.1087 (17)0.0772 (14)0.0137 (15)0.0145 (13)0.0291 (12)
N6B0.0712 (15)0.0898 (17)0.0529 (13)0.0161 (13)0.0015 (11)0.0063 (12)
C7B0.0491 (15)0.161 (3)0.0627 (16)0.0108 (17)0.0101 (12)0.0000 (17)
C8B0.0443 (12)0.0739 (15)0.0475 (12)0.0047 (10)0.0105 (10)0.0010 (10)
C9B0.0485 (13)0.0830 (16)0.0463 (12)0.0003 (11)0.0183 (11)0.0036 (11)
C10B0.0441 (12)0.0677 (14)0.0423 (11)0.0020 (10)0.0114 (9)0.0009 (10)
C11B0.0436 (12)0.0952 (18)0.0487 (13)0.0038 (12)0.0112 (10)0.0032 (12)
C12B0.0507 (14)0.1058 (19)0.0449 (13)0.0032 (13)0.0173 (11)0.0041 (12)
C13B0.0486 (13)0.0741 (15)0.0409 (12)0.0076 (11)0.0083 (10)0.0022 (10)
C14B0.0481 (13)0.0926 (18)0.0444 (12)0.0005 (12)0.0137 (11)0.0012 (11)
C15B0.0446 (12)0.0875 (17)0.0426 (12)0.0035 (11)0.0069 (10)0.0025 (11)
C16B0.0604 (15)0.0727 (16)0.0593 (15)0.0090 (12)0.0022 (12)0.0038 (12)
C17B0.0601 (14)0.0746 (16)0.0561 (14)0.0014 (12)0.0067 (12)0.0092 (12)
C18B0.0507 (13)0.0717 (15)0.0484 (13)0.0107 (11)0.0023 (11)0.0071 (11)
C19B0.0586 (14)0.0637 (14)0.0648 (16)0.0007 (11)0.0056 (12)0.0063 (12)
C20B0.0606 (15)0.0724 (16)0.0572 (15)0.0012 (12)0.0097 (12)0.0074 (12)
Geometric parameters (Å, º) top
O1A—C13A1.357 (2)O1B—C13B1.357 (3)
O1A—H1A0.8200O1B—H1B0.8200
O2A—C14A1.205 (2)O2B—C14B1.195 (3)
O3A—C14A1.354 (2)O3B—C14B1.352 (3)
O3A—C15A1.399 (2)O3B—C15B1.399 (3)
O4A—N6A1.201 (3)O4B—N6B1.209 (3)
O5A—N6A1.204 (3)O5B—N6B1.214 (3)
N6A—C18A1.465 (3)N6B—C18B1.470 (3)
C7A—C8A1.501 (3)C7B—C8B1.505 (3)
C7A—H7A10.9600C7B—H7B10.9600
C7A—H7A20.9600C7B—H7B20.9600
C7A—H7A30.9600C7B—H7B30.9600
C8A—C9A1.377 (3)C8B—C9B1.374 (3)
C8A—C13A1.396 (3)C8B—C13B1.390 (3)
C9A—C10A1.390 (3)C9B—C10B1.389 (3)
C9A—H9A0.9300C9B—H9B0.9300
C10A—C11A1.388 (3)C10B—C11B1.384 (3)
C10A—C14A1.459 (3)C10B—C14B1.454 (3)
C11A—C12A1.371 (3)C11B—C12B1.367 (3)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.385 (3)C12B—C13B1.377 (3)
C12A—H12A0.9300C12B—H12B0.9300
C15A—C16A1.369 (3)C15B—C20B1.369 (3)
C15A—C20A1.370 (3)C15B—C16B1.374 (3)
C16A—C17A1.381 (3)C16B—C17B1.378 (3)
C16A—H16A0.9300C16B—H16B0.9300
C17A—C18A1.373 (3)C17B—C18B1.376 (3)
C17A—H17A0.9300C17B—H17B0.9300
C18A—C19A1.370 (3)C18B—C19B1.367 (3)
C19A—C20A1.378 (3)C19B—C20B1.379 (3)
C19A—H19A0.9300C19B—H19B0.9300
C20A—H20A0.9300C20B—H20B0.9300
C13A—O1A—H1A109.5C13B—O1B—H1B109.5
C14A—O3A—C15A116.73 (15)C14B—O3B—C15B117.38 (17)
O4A—N6A—O5A122.6 (2)O4B—N6B—O5B123.4 (2)
O4A—N6A—C18A119.2 (2)O4B—N6B—C18B117.7 (3)
O5A—N6A—C18A118.2 (2)O5B—N6B—C18B118.9 (2)
C8A—C7A—H7A1109.5C8B—C7B—H7B1109.5
C8A—C7A—H7A2109.5C8B—C7B—H7B2109.5
H7A1—C7A—H7A2109.5H7B1—C7B—H7B2109.5
C8A—C7A—H7A3109.5C8B—C7B—H7B3109.5
H7A1—C7A—H7A3109.5H7B1—C7B—H7B3109.5
H7A2—C7A—H7A3109.5H7B2—C7B—H7B3109.5
C9A—C8A—C13A117.47 (17)C9B—C8B—C13B117.3 (2)
C9A—C8A—C7A122.07 (17)C9B—C8B—C7B122.7 (2)
C13A—C8A—C7A120.43 (17)C13B—C8B—C7B120.0 (2)
C8A—C9A—C10A122.14 (17)C8B—C9B—C10B122.36 (19)
C8A—C9A—H9A118.9C8B—C9B—H9B118.8
C10A—C9A—H9A118.9C10B—C9B—H9B118.8
C11A—C10A—C9A118.95 (17)C11B—C10B—C9B118.8 (2)
C11A—C10A—C14A122.36 (17)C11B—C10B—C14B122.1 (2)
C9A—C10A—C14A118.62 (16)C9B—C10B—C14B119.12 (19)
C12A—C11A—C10A120.06 (18)C12B—C11B—C10B119.9 (2)
C12A—C11A—H11A120.0C12B—C11B—H11B120.1
C10A—C11A—H11A120.0C10B—C11B—H11B120.1
C11A—C12A—C13A120.17 (17)C11B—C12B—C13B120.5 (2)
C11A—C12A—H12A119.9C11B—C12B—H12B119.8
C13A—C12A—H12A119.9C13B—C12B—H12B119.8
O1A—C13A—C12A122.05 (17)O1B—C13B—C12B122.19 (19)
O1A—C13A—C8A116.87 (17)O1B—C13B—C8B116.57 (19)
C12A—C13A—C8A121.08 (17)C12B—C13B—C8B121.2 (2)
O2A—C14A—O3A120.82 (17)O2B—C14B—O3B120.8 (2)
O2A—C14A—C10A126.02 (18)O2B—C14B—C10B125.9 (2)
O3A—C14A—C10A113.15 (16)O3B—C14B—C10B113.31 (18)
C16A—C15A—C20A122.09 (19)C20B—C15B—C16B122.1 (2)
C16A—C15A—O3A118.98 (18)C20B—C15B—O3B118.5 (2)
C20A—C15A—O3A118.86 (19)C16B—C15B—O3B119.3 (2)
C15A—C16A—C17A119.05 (19)C15B—C16B—C17B118.8 (2)
C15A—C16A—H16A120.5C15B—C16B—H16B120.6
C17A—C16A—H16A120.5C17B—C16B—H16B120.6
C18A—C17A—C16A118.60 (19)C18B—C17B—C16B118.6 (2)
C18A—C17A—H17A120.7C18B—C17B—H17B120.7
C16A—C17A—H17A120.7C16B—C17B—H17B120.7
C19A—C18A—C17A122.41 (19)C19B—C18B—C17B122.6 (2)
C19A—C18A—N6A118.49 (18)C19B—C18B—N6B118.6 (2)
C17A—C18A—N6A119.10 (19)C17B—C18B—N6B118.8 (2)
C18A—C19A—C20A118.71 (19)C18B—C19B—C20B118.5 (2)
C18A—C19A—H19A120.6C18B—C19B—H19B120.8
C20A—C19A—H19A120.6C20B—C19B—H19B120.8
C15A—C20A—C19A119.1 (2)C15B—C20B—C19B119.3 (2)
C15A—C20A—H20A120.4C15B—C20B—H20B120.4
C19A—C20A—H20A120.4C19B—C20B—H20B120.4
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O2Ai0.821.942.753 (2)172
O1B—H1B···O2Bii0.821.942.727 (3)160
C7B—H7B1···O4Aiii0.962.503.418 (3)159
C12A—H12A···O2Ai0.932.543.245 (2)132
C19B—H19B···O5Aiv0.932.583.476 (4)163
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z+1/2; (iii) x+1/2, y+3/2, z+1; (iv) x, y+2, z1/2.

Experimental details

Crystal data
Chemical formulaC14H11NO5
Mr273.24
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)42.313 (6), 8.0047 (11), 16.1078 (18)
β (°) 105.819 (4)
V3)5249.2 (12)
Z16
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.24 × 0.20 × 0.16
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionψ scan
(SADABS; Sheldrick, 2007)
Tmin, Tmax0.975, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
28460, 4602, 3349
Rint0.054
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.143, 1.02
No. of reflections4602
No. of parameters361
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O1A—H1A···O2Ai0.821.942.753 (2)172
O1B—H1B···O2Bii0.821.942.727 (3)160
C7B—H7B1···O4Aiii0.962.503.418 (3)159
C12A—H12A···O2Ai0.932.543.245 (2)132
C19B—H19B···O5Aiv0.932.583.476 (4)163
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z+1/2; (iii) x+1/2, y+3/2, z+1; (iv) x, y+2, z1/2.
 

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

First citationBruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationGhosh, P. P., Pal, G., Paul, S. & Das, A. R. (2012). Green Chem. 14, 2691–2698.  Web of Science CSD CrossRef CAS
First citationSheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSugiyama, T., Meng, J., Wen, Z., Li, J. & Matsuura, T. (2002). Mol. Cryst. Liq. Cryst. 389, 17–23.  Web of Science CrossRef CAS

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds