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

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ISSN: 2056-9890

Ethyl 2-(5-meth­­oxy-2-methyl-1H-indol-3-yl)acetate

aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, bChemistry Department, Faculty of Science, Mini University, 61519 El-Minia, Egypt, cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com

(Received 1 July 2013; accepted 4 July 2013; online 13 July 2013)

In the title compound, C14H17NO3, the nine-membered 1H-indole ring system is essentially planar [maximum deviation = 0.019 (1) Å]. In the crystal, mol­ecules are linked via N—H⋯O hydrogen bonds, forming chains along [001]. These chains are linked via C—H⋯O hydrogen bonds and C—H⋯π inter­actions, forming a two-dimensional network lying parallel to the ac plane.

Related literature

For medicinal applications of the drug indomethacin (systematic name: 2-{1-[(4-chloro­phen­yl)carbon­yl]-5-meth­oxy-2-methyl-1H-indol-3-yl}acetic acid), see: Paneth (1995[Paneth, N. S. (1995). Future Child, 5, 19-34.]); McIntyre et al. (2001[McIntyre, J., van Overmeire, B. & van den Anker, J. N. (2001). Paediatr. Perinat. Drug Ther. 4, 85-91.]); Abou-Ghannam et al. (2012[Abou-Ghannam, G. M. D., Ihab, M., Usta, M. D., Anwar, H. & Nassar, M. D. (2012). Am. J. Perinatol. 29, 175-186.]). For the synthesis and reactions of indomethacin with other non-steroidal anti-inflammatory mol­ecules, see: Mohamed et al. (2012[Mohamed, S. K., Albayati, M. R., Omara, W. A. M., Abdelhamid, A. A., Potgeiter, H., Hameed, A. S. & Al-Janabi, K. M. (2012). J. Chem. Pharm. Res. 4, 3505-3517.]).

[Scheme 1]

Experimental

Crystal data
  • C14H17NO3

  • Mr = 247.29

  • Monoclinic, P 21 /c

  • a = 7.8117 (5) Å

  • b = 17.1953 (12) Å

  • c = 9.9003 (7) Å

  • β = 106.756 (1)°

  • V = 1273.39 (15) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 150 K

  • 0.23 × 0.21 × 0.06 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.84, Tmax = 1.00

  • 22947 measured reflections

  • 3374 independent reflections

  • 2889 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.117

  • S = 1.08

  • 3374 reflections

  • 170 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O2i 0.914 (18) 2.013 (18) 2.8987 (14) 162.7 (16)
C7—H7B⋯O2ii 0.98 2.57 3.4271 (18) 146
C13—H13A⋯O1iii 0.99 2.55 3.4236 (16) 148
C7—H7ACg1iv 0.98 2.99 3.9550 (16) 169
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Indomethacin, chemically named 2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid is a non-steroidal drug (NSAID) and is commonly used as an anti-inflammatory drug by inhibiting cyclooxygenase (COX) 1 and 2 enzymes. It also clinically used as a tocolytic agent to delay premature labor (preterm birth; PTB), reduce amniotic fluid in polyhydramnios, and to close patent ductus arteriosus (PDA). PTB is a major cause of neonatal morbidity and mortality worldwide (Paneth, 1995; McIntyre et al., 2001; Abou-Ghannam et al., 2012). In view of these facts and as part of our ongoing study incorporating NSAID's as a substructure in the synthesis of potential bio-active pharmacophors (Mohamed et al., 2012), indomethacin has been hydrolysed during its esterification in acidic medium with ethanol to afforded the title corresponding ethyl ester.

In the title compound, Fig. 1, the nine-membered 1H-indole ring system (N1/C1–C6/C8/C9) is essentially planar with a maximum deviation of 0.019 (1) Å for N1. The C2–C3–O1–C7, C1–C9–C8–C10, C1–C9–C11–C12, C9–C11–C12–O2, C11–C12–O3–C13 and C12–O3–C13–C14 torsion angles are -6.53 (18), -177.77 (12), 117.42 (13), -69.51 (15), 177.50 (9) and 171.98 (10)°, respectively.

In the crystal, molecules are linked via N-H···O hydrogen bonds forming chains along [001]. These chains are linked via C-H···O hydrogen bonds and C-H···π interactions forming a two-dimensional network lying parallel to the ac plane (Fig. 2 and Table 1).

Related literature top

For medicinal applications of drug indomethacin (systematic name: 2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid), see: Paneth (1995); McIntyre et al. (2001); Abou-Ghannam et al. (2012). For the synthesis and reactions of indomethacin with other non-steroidal anti-inflammatory molecules, see: Mohamed et al. (2012).

Experimental top

A mixture of 0.03 mol indomethacin (10.57 g m) in 150 ml of absolute ethanol and 6 ml of concentrated H2SO4 was refluxed for 6 h. The mixture was cooled to room temperature and neutralized with NaHCO3 solution. The ester was separated as an organic layer, washed with water and extracted with diethyl ether (3 × 50mL). The combined ether layers were dried over MgSO4, filtered and left for 3–4 days until brown crystals formed. The solid was collected and recrystallized from cyclohexane to give the pure ester as silver-coloured crystals (m.p. 347–350 K) suitable for X-ray diffraction. Spectroscopic data for the title compound are available in the archived CIF.

Refinement top

The C-bound H atoms were placed geometrically [C—H = 0.95 Å (aromatic H), C—H = 0.98 Å (methyl H) and 0.99 Å (methylene H)], and refined using a riding model with Uiso(H) = 1.5Ueq(C-methyl) and = 1.2Ueq(C) for other H atoms. The N-bound H atom was located in a difference Fourier synthesis and freely refined [N1—H1 = 0.914 (18) Å].

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); 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, 2012) and DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A perspective view along the c axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines - see Table 1 for details.
Ethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate top
Crystal data top
C14H17NO3F(000) = 528
Mr = 247.29Dx = 1.290 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9989 reflections
a = 7.8117 (5) Åθ = 2.4–29.1°
b = 17.1953 (12) ŵ = 0.09 mm1
c = 9.9003 (7) ÅT = 150 K
β = 106.756 (1)°Plate, colourless
V = 1273.39 (15) Å30.23 × 0.21 × 0.06 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
3374 independent reflections
Radiation source: fine-focus sealed tube2889 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: 8.3660 pixels mm-1θmax = 29.1°, θmin = 2.4°
ϕ and ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
k = 2323
Tmin = 0.84, Tmax = 1.00l = 1313
22947 measured reflections
Refinement top
Refinement on F2Primary atom site location: difference Fourier map
Least-squares matrix: fullSecondary atom site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: difference Fourier map
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.08 W = 1/[Σ2(Fo2) + (0.0539P)2 + 0.3155P]
where P = (Fo2 + 2Fc2)/3
3374 reflections(Δ/σ)max < 0.001
170 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C14H17NO3V = 1273.39 (15) Å3
Mr = 247.29Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.8117 (5) ŵ = 0.09 mm1
b = 17.1953 (12) ÅT = 150 K
c = 9.9003 (7) Å0.23 × 0.21 × 0.06 mm
β = 106.756 (1)°
Data collection top
Bruker SMART APEX CCD
diffractometer
3374 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
2889 reflections with I > 2σ(I)
Tmin = 0.84, Tmax = 1.00Rint = 0.043
22947 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.31 e Å3
3374 reflectionsΔρmin = 0.24 e Å3
170 parameters
Special details top

Experimental. Spectroscopic data for the title compound: IR (KBr cm-1): (C=O ester 1728), (NH 3317), (C—H aliphatic, 2833–2924), (C—H, Ar, 2975–3002). 1H-NMR: (DMSO-D6) δ at 1.3(t, 3H, CH3 of ethyl group), 4.0(q, 2H, –CH2 aliphatic in ethyl group), 2.3(s, 3H, CH3), 3.4(s, –CH2), 3.7(s, 3H, –OCH3), 10.8(s, 1H, –NH), 6.8(s, 1H, Ar), 6.6(d, 1H, Ar), 7.2(d, 1H, Ar). 13C-NMR: 171 (C=O ester), 11(CH3 in indole), 14(CH3 of ethyl group), 29(–CH2), 55 (–OCH3), 59(–CH2 of ethyl group). 99, 103, 109, 110, 128, 129, 133,152 (8 C, aromatics). There are two signals at 29 and 59 p.p.m. oriented downward in the DEPT spectrum confirming the existence of two –CH2 groups.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O10.17116 (13)0.36046 (6)0.24184 (10)0.0376 (3)
O20.75724 (12)0.08270 (5)0.02263 (9)0.0312 (3)
O30.75501 (11)0.01325 (4)0.16773 (9)0.0251 (2)
N10.65214 (13)0.29386 (6)0.27056 (11)0.0264 (3)
C10.47230 (14)0.25588 (6)0.05968 (12)0.0216 (3)
C20.34868 (15)0.26677 (6)0.07390 (13)0.0240 (3)
C30.29070 (16)0.34165 (7)0.11378 (13)0.0282 (3)
C40.35262 (18)0.40558 (7)0.02372 (15)0.0336 (4)
C50.47322 (17)0.39589 (7)0.10729 (15)0.0309 (3)
C60.53295 (15)0.32062 (6)0.14800 (13)0.0245 (3)
C70.09045 (18)0.29785 (9)0.33106 (15)0.0367 (4)
C80.66375 (15)0.21415 (7)0.26458 (12)0.0243 (3)
C90.55670 (14)0.18869 (6)0.13595 (12)0.0220 (3)
C100.77677 (16)0.16917 (8)0.38672 (13)0.0312 (4)
C110.52395 (15)0.10556 (6)0.08854 (13)0.0258 (3)
C120.68958 (14)0.06698 (6)0.06967 (12)0.0224 (3)
C130.91945 (15)0.02529 (7)0.16271 (13)0.0272 (3)
C140.98064 (19)0.07392 (8)0.29348 (16)0.0395 (4)
H10.700 (2)0.3250 (10)0.347 (2)0.052 (5)*
H20.306200.223900.135000.0290*
H40.310300.456300.054100.0400*
H50.514400.439000.168000.0370*
H7A0.183000.267500.356100.0550*
H7B0.006000.318400.417000.0550*
H7C0.026600.264400.281600.0550*
H10A0.726400.117000.387100.0470*
H10B0.779600.196000.474700.0470*
H10C0.898500.165000.378600.0470*
H11A0.427800.103800.002000.0310*
H11B0.482500.076100.159100.0310*
H13A1.011700.013700.160000.0330*
H13B0.896900.058400.077600.0330*
H14A1.007400.040200.376700.0590*
H14B1.088500.102700.292400.0590*
H14C0.886100.110700.296900.0590*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0347 (5)0.0333 (5)0.0417 (5)0.0089 (4)0.0059 (4)0.0110 (4)
O20.0383 (5)0.0288 (4)0.0283 (4)0.0066 (4)0.0124 (4)0.0065 (3)
O30.0260 (4)0.0219 (4)0.0277 (4)0.0049 (3)0.0084 (3)0.0047 (3)
N10.0275 (5)0.0268 (5)0.0265 (5)0.0049 (4)0.0104 (4)0.0073 (4)
C10.0206 (5)0.0194 (5)0.0273 (5)0.0005 (4)0.0111 (4)0.0010 (4)
C20.0233 (5)0.0217 (5)0.0283 (6)0.0017 (4)0.0093 (4)0.0001 (4)
C30.0258 (5)0.0269 (6)0.0340 (6)0.0052 (4)0.0122 (5)0.0067 (5)
C40.0348 (6)0.0200 (5)0.0503 (8)0.0051 (5)0.0191 (6)0.0048 (5)
C50.0352 (6)0.0196 (5)0.0432 (7)0.0024 (5)0.0198 (6)0.0048 (5)
C60.0251 (5)0.0222 (5)0.0299 (6)0.0027 (4)0.0140 (4)0.0039 (4)
C70.0297 (6)0.0455 (8)0.0335 (7)0.0111 (5)0.0071 (5)0.0055 (6)
C80.0227 (5)0.0268 (5)0.0255 (5)0.0017 (4)0.0104 (4)0.0018 (4)
C90.0199 (5)0.0205 (5)0.0265 (5)0.0002 (4)0.0080 (4)0.0006 (4)
C100.0282 (6)0.0394 (7)0.0249 (6)0.0023 (5)0.0058 (5)0.0005 (5)
C110.0216 (5)0.0191 (5)0.0345 (6)0.0002 (4)0.0047 (4)0.0003 (4)
C120.0239 (5)0.0164 (5)0.0243 (5)0.0006 (4)0.0027 (4)0.0016 (4)
C130.0244 (5)0.0247 (5)0.0323 (6)0.0060 (4)0.0080 (5)0.0028 (5)
C140.0364 (7)0.0369 (7)0.0444 (8)0.0134 (6)0.0106 (6)0.0145 (6)
Geometric parameters (Å, º) top
O1—C31.3789 (16)C11—C121.5128 (16)
O1—C71.4198 (18)C13—C141.4990 (19)
O2—C121.2108 (15)C2—H20.9500
O3—C121.3309 (13)C4—H40.9500
O3—C131.4590 (15)C5—H50.9500
N1—C61.3782 (16)C7—H7A0.9800
N1—C81.3760 (16)C7—H7B0.9800
N1—H10.914 (18)C7—H7C0.9800
C1—C21.4072 (17)C10—H10A0.9800
C1—C61.4105 (15)C10—H10B0.9800
C1—C91.4327 (15)C10—H10C0.9800
C2—C31.3841 (16)C11—H11A0.9900
C3—C41.4102 (18)C11—H11B0.9900
C4—C51.376 (2)C13—H13A0.9900
C5—C61.3953 (16)C13—H13B0.9900
C8—C91.3779 (16)C14—H14A0.9800
C8—C101.4914 (17)C14—H14B0.9800
C9—C111.5033 (15)C14—H14C0.9800
C3—O1—C7117.11 (11)C5—C4—H4119.00
C12—O3—C13116.57 (9)C4—C5—H5121.00
C6—N1—C8109.32 (10)C6—C5—H5121.00
C6—N1—H1123.0 (11)O1—C7—H7A109.00
C8—N1—H1127.1 (11)O1—C7—H7B109.00
C2—C1—C6119.63 (10)O1—C7—H7C109.00
C6—C1—C9106.77 (10)H7A—C7—H7B109.00
C2—C1—C9133.59 (10)H7A—C7—H7C109.00
C1—C2—C3118.12 (10)H7B—C7—H7C109.00
O1—C3—C2124.03 (11)C8—C10—H10A109.00
O1—C3—C4114.61 (11)C8—C10—H10B109.00
C2—C3—C4121.36 (12)C8—C10—H10C109.00
C3—C4—C5121.23 (11)H10A—C10—H10B109.00
C4—C5—C6117.76 (12)H10A—C10—H10C109.00
C1—C6—C5121.90 (11)H10B—C10—H10C109.00
N1—C6—C5130.45 (11)C9—C11—H11A109.00
N1—C6—C1107.65 (9)C9—C11—H11B109.00
N1—C8—C9109.04 (10)C12—C11—H11A109.00
N1—C8—C10120.84 (11)C12—C11—H11B109.00
C9—C8—C10130.11 (11)H11A—C11—H11B108.00
C1—C9—C8107.18 (10)O3—C13—H13A110.00
C8—C9—C11126.44 (10)O3—C13—H13B110.00
C1—C9—C11126.24 (10)C14—C13—H13A110.00
C9—C11—C12112.39 (10)C14—C13—H13B110.00
O2—C12—O3123.10 (11)H13A—C13—H13B109.00
O2—C12—C11124.77 (10)C13—C14—H14A110.00
O3—C12—C11112.13 (10)C13—C14—H14B109.00
O3—C13—C14106.78 (10)C13—C14—H14C110.00
C1—C2—H2121.00H14A—C14—H14B109.00
C3—C2—H2121.00H14A—C14—H14C109.00
C3—C4—H4119.00H14B—C14—H14C109.00
C7—O1—C3—C26.53 (18)C6—C1—C9—C80.25 (13)
C7—O1—C3—C4173.81 (12)C6—C1—C9—C11175.68 (11)
C13—O3—C12—O22.08 (16)C1—C2—C3—O1179.49 (11)
C13—O3—C12—C11177.50 (9)C1—C2—C3—C40.15 (19)
C12—O3—C13—C14171.98 (10)O1—C3—C4—C5179.64 (13)
C8—N1—C6—C12.16 (14)C2—C3—C4—C50.0 (2)
C8—N1—C6—C5177.77 (13)C3—C4—C5—C60.3 (2)
C6—N1—C8—C92.03 (14)C4—C5—C6—N1179.64 (13)
C6—N1—C8—C10176.93 (11)C4—C5—C6—C10.4 (2)
C6—C1—C2—C30.02 (17)N1—C8—C9—C11.07 (13)
C9—C1—C2—C3178.39 (13)N1—C8—C9—C11176.98 (11)
C2—C1—C6—N1179.74 (11)C10—C8—C9—C1177.77 (12)
C2—C1—C6—C50.33 (18)C10—C8—C9—C111.9 (2)
C9—C1—C6—N11.47 (13)C1—C9—C11—C12117.42 (13)
C9—C1—C6—C5178.47 (12)C8—C9—C11—C1267.42 (15)
C2—C1—C9—C8178.81 (13)C9—C11—C12—O269.51 (15)
C2—C1—C9—C112.9 (2)C9—C11—C12—O3110.07 (11)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.914 (18)2.013 (18)2.8987 (14)162.7 (16)
C7—H7B···O2ii0.982.573.4271 (18)146
C13—H13A···O1iii0.992.553.4236 (16)148
C7—H7A···Cg1iv0.982.993.9550 (16)169
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x1, y+1/2, z1/2; (iii) x+1, y+1/2, z+1/2; (iv) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC14H17NO3
Mr247.29
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)7.8117 (5), 17.1953 (12), 9.9003 (7)
β (°) 106.756 (1)
V3)1273.39 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.23 × 0.21 × 0.06
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2013)
Tmin, Tmax0.84, 1.00
No. of measured, independent and
observed [I > 2σ(I)] reflections
22947, 3374, 2889
Rint0.043
(sin θ/λ)max1)0.685
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.117, 1.08
No. of reflections3374
No. of parameters170
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.31, 0.24

Computer programs: APEX2 (Bruker, 2013), SAINT (Bruker, 2013), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Putz, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.914 (18)2.013 (18)2.8987 (14)162.7 (16)
C7—H7B···O2ii0.982.573.4271 (18)146
C13—H13A···O1iii0.992.553.4236 (16)148
C7—H7A···Cg1iv0.982.993.9550 (16)169
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x1, y+1/2, z1/2; (iii) x+1, y+1/2, z+1/2; (iv) x, y+1/2, z1/2.
 

Acknowledgements

Manchester Metropolitan University, Tulane University and Erciyes University are gratefully acknowledged for supporting this study.

References

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