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

Mohamed, S.K.; Mague, J.T.; Akkurt, M.; Hasan, A.A.; Albayati, M.R.

doi:10.1107/S1600536813018618

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1242

doi:10.1107/S1600536813018618

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

Shaaban K. Mohamed,^a,^b Joel T. Mague,^c Mehmet Akkurt,^d Alaa A. Hassan ^b and Mustafa R. Albayati ^e ^*

^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 ); 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

Crystal data

C₁₄H₁₇NO₃
M_r = 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 ) T_min = 0.84, T_max = 1.00
22947 measured reflections
3374 independent reflections
2889 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.31 e Å⁻³
Δρ_min = −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	D⋯A	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—H7A⋯Cg1^iv	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); cell refinement: SAINT (Bruker, 2013); 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 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg & Putz, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813018618/su2618sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813018618/su2618Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813018618/su2618Isup3.cml

checkCIF report

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.

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

	Fig. 1. The molecular structure of the title molecule, with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	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

C₁₄H₁₇NO₃	F(000) = 528
M_r = 247.29	D_x = 1.290 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9989 reflections
a = 7.8117 (5) Å	θ = 2.4–29.1°
b = 17.1953 (12) Å	µ = 0.09 mm⁻¹
c = 9.9003 (7) Å	T = 150 K
β = 106.756 (1)°	Plate, colourless
V = 1273.39 (15) Å³	0.23 × 0.21 × 0.06 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	3374 independent reflections
Radiation source: fine-focus sealed tube	2889 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
Detector resolution: 8.3660 pixels mm^-1	θ_max = 29.1°, θ_min = 2.4°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −23→23
T_min = 0.84, T_max = 1.00	l = −13→13
22947 measured reflections

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: difference Fourier map
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	W = 1/[Σ²(F_o²) + (0.0539P)² + 0.3155P] where P = (F_o² + 2F_c²)/3
3374 reflections	(Δ/σ)_max < 0.001
170 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₄H₁₇NO₃	V = 1273.39 (15) Å³
M_r = 247.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.8117 (5) Å	µ = 0.09 mm⁻¹
b = 17.1953 (12) Å	T = 150 K
c = 9.9003 (7) Å	0.23 × 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)
T_min = 0.84, T_max = 1.00	R_int = 0.043
22947 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.31 e Å⁻³
3374 reflections	Δρ_min = −0.24 e Å⁻³
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

	x	y	z	U_iso*/U_eq
O1	0.17116 (13)	0.36046 (6)	−0.24184 (10)	0.0376 (3)
O2	0.75724 (12)	0.08270 (5)	−0.02263 (9)	0.0312 (3)
O3	0.75501 (11)	0.01325 (4)	0.16773 (9)	0.0251 (2)
N1	0.65214 (13)	0.29386 (6)	0.27056 (11)	0.0264 (3)
C1	0.47230 (14)	0.25588 (6)	0.05968 (12)	0.0216 (3)
C2	0.34868 (15)	0.26677 (6)	−0.07390 (13)	0.0240 (3)
C3	0.29070 (16)	0.34165 (7)	−0.11378 (13)	0.0282 (3)
C4	0.35262 (18)	0.40558 (7)	−0.02372 (15)	0.0336 (4)
C5	0.47322 (17)	0.39589 (7)	0.10729 (15)	0.0309 (3)
C6	0.53295 (15)	0.32062 (6)	0.14800 (13)	0.0245 (3)
C7	0.09045 (18)	0.29785 (9)	−0.33106 (15)	0.0367 (4)
C8	0.66375 (15)	0.21415 (7)	0.26458 (12)	0.0243 (3)
C9	0.55670 (14)	0.18869 (6)	0.13595 (12)	0.0220 (3)
C10	0.77677 (16)	0.16917 (8)	0.38672 (13)	0.0312 (4)
C11	0.52395 (15)	0.10556 (6)	0.08854 (13)	0.0258 (3)
C12	0.68958 (14)	0.06698 (6)	0.06967 (12)	0.0224 (3)
C13	0.91945 (15)	−0.02529 (7)	0.16271 (13)	0.0272 (3)
C14	0.98064 (19)	−0.07392 (8)	0.29348 (16)	0.0395 (4)
H1	0.700 (2)	0.3250 (10)	0.347 (2)	0.052 (5)*
H2	0.30620	0.22390	−0.13500	0.0290*
H4	0.31030	0.45630	−0.05410	0.0400*
H5	0.51440	0.43900	0.16800	0.0370*
H7A	0.18300	0.26750	−0.35610	0.0550*
H7B	0.00600	0.31840	−0.41700	0.0550*
H7C	0.02660	0.26440	−0.28160	0.0550*
H10A	0.72640	0.11700	0.38710	0.0470*
H10B	0.77960	0.19600	0.47470	0.0470*
H10C	0.89850	0.16500	0.37860	0.0470*
H11A	0.42780	0.10380	−0.00200	0.0310*
H11B	0.48250	0.07610	0.15910	0.0310*
H13A	1.01170	0.01370	0.16000	0.0330*
H13B	0.89690	−0.05840	0.07760	0.0330*
H14A	1.00740	−0.04020	0.37670	0.0590*
H14B	1.08850	−0.10270	0.29240	0.0590*
H14C	0.88610	−0.11070	0.29690	0.0590*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0347 (5)	0.0333 (5)	0.0417 (5)	0.0089 (4)	0.0059 (4)	0.0110 (4)
O2	0.0383 (5)	0.0288 (4)	0.0283 (4)	0.0066 (4)	0.0124 (4)	0.0065 (3)
O3	0.0260 (4)	0.0219 (4)	0.0277 (4)	0.0049 (3)	0.0084 (3)	0.0047 (3)
N1	0.0275 (5)	0.0268 (5)	0.0265 (5)	−0.0049 (4)	0.0104 (4)	−0.0073 (4)
C1	0.0206 (5)	0.0194 (5)	0.0273 (5)	−0.0005 (4)	0.0111 (4)	−0.0010 (4)
C2	0.0233 (5)	0.0217 (5)	0.0283 (6)	0.0017 (4)	0.0093 (4)	−0.0001 (4)
C3	0.0258 (5)	0.0269 (6)	0.0340 (6)	0.0052 (4)	0.0122 (5)	0.0067 (5)
C4	0.0348 (6)	0.0200 (5)	0.0503 (8)	0.0051 (5)	0.0191 (6)	0.0048 (5)
C5	0.0352 (6)	0.0196 (5)	0.0432 (7)	−0.0024 (5)	0.0198 (6)	−0.0048 (5)
C6	0.0251 (5)	0.0222 (5)	0.0299 (6)	−0.0027 (4)	0.0140 (4)	−0.0039 (4)
C7	0.0297 (6)	0.0455 (8)	0.0335 (7)	0.0111 (5)	0.0071 (5)	0.0055 (6)
C8	0.0227 (5)	0.0268 (5)	0.0255 (5)	−0.0017 (4)	0.0104 (4)	−0.0018 (4)
C9	0.0199 (5)	0.0205 (5)	0.0265 (5)	−0.0002 (4)	0.0080 (4)	−0.0006 (4)
C10	0.0282 (6)	0.0394 (7)	0.0249 (6)	0.0023 (5)	0.0058 (5)	0.0005 (5)
C11	0.0216 (5)	0.0191 (5)	0.0345 (6)	−0.0002 (4)	0.0047 (4)	−0.0003 (4)
C12	0.0239 (5)	0.0164 (5)	0.0243 (5)	−0.0006 (4)	0.0027 (4)	−0.0016 (4)
C13	0.0244 (5)	0.0247 (5)	0.0323 (6)	0.0060 (4)	0.0080 (5)	0.0028 (5)
C14	0.0364 (7)	0.0369 (7)	0.0444 (8)	0.0134 (6)	0.0106 (6)	0.0145 (6)

Geometric parameters (Å, º) top

O1—C3	1.3789 (16)	C11—C12	1.5128 (16)
O1—C7	1.4198 (18)	C13—C14	1.4990 (19)
O2—C12	1.2108 (15)	C2—H2	0.9500
O3—C12	1.3309 (13)	C4—H4	0.9500
O3—C13	1.4590 (15)	C5—H5	0.9500
N1—C6	1.3782 (16)	C7—H7A	0.9800
N1—C8	1.3760 (16)	C7—H7B	0.9800
N1—H1	0.914 (18)	C7—H7C	0.9800
C1—C2	1.4072 (17)	C10—H10A	0.9800
C1—C6	1.4105 (15)	C10—H10B	0.9800
C1—C9	1.4327 (15)	C10—H10C	0.9800
C2—C3	1.3841 (16)	C11—H11A	0.9900
C3—C4	1.4102 (18)	C11—H11B	0.9900
C4—C5	1.376 (2)	C13—H13A	0.9900
C5—C6	1.3953 (16)	C13—H13B	0.9900
C8—C9	1.3779 (16)	C14—H14A	0.9800
C8—C10	1.4914 (17)	C14—H14B	0.9800
C9—C11	1.5033 (15)	C14—H14C	0.9800

C3—O1—C7	117.11 (11)	C5—C4—H4	119.00
C12—O3—C13	116.57 (9)	C4—C5—H5	121.00
C6—N1—C8	109.32 (10)	C6—C5—H5	121.00
C6—N1—H1	123.0 (11)	O1—C7—H7A	109.00
C8—N1—H1	127.1 (11)	O1—C7—H7B	109.00
C2—C1—C6	119.63 (10)	O1—C7—H7C	109.00
C6—C1—C9	106.77 (10)	H7A—C7—H7B	109.00
C2—C1—C9	133.59 (10)	H7A—C7—H7C	109.00
C1—C2—C3	118.12 (10)	H7B—C7—H7C	109.00
O1—C3—C2	124.03 (11)	C8—C10—H10A	109.00
O1—C3—C4	114.61 (11)	C8—C10—H10B	109.00
C2—C3—C4	121.36 (12)	C8—C10—H10C	109.00
C3—C4—C5	121.23 (11)	H10A—C10—H10B	109.00
C4—C5—C6	117.76 (12)	H10A—C10—H10C	109.00
C1—C6—C5	121.90 (11)	H10B—C10—H10C	109.00
N1—C6—C5	130.45 (11)	C9—C11—H11A	109.00
N1—C6—C1	107.65 (9)	C9—C11—H11B	109.00
N1—C8—C9	109.04 (10)	C12—C11—H11A	109.00
N1—C8—C10	120.84 (11)	C12—C11—H11B	109.00
C9—C8—C10	130.11 (11)	H11A—C11—H11B	108.00
C1—C9—C8	107.18 (10)	O3—C13—H13A	110.00
C8—C9—C11	126.44 (10)	O3—C13—H13B	110.00
C1—C9—C11	126.24 (10)	C14—C13—H13A	110.00
C9—C11—C12	112.39 (10)	C14—C13—H13B	110.00
O2—C12—O3	123.10 (11)	H13A—C13—H13B	109.00
O2—C12—C11	124.77 (10)	C13—C14—H14A	110.00
O3—C12—C11	112.13 (10)	C13—C14—H14B	109.00
O3—C13—C14	106.78 (10)	C13—C14—H14C	110.00
C1—C2—H2	121.00	H14A—C14—H14B	109.00
C3—C2—H2	121.00	H14A—C14—H14C	109.00
C3—C4—H4	119.00	H14B—C14—H14C	109.00

C7—O1—C3—C2	6.53 (18)	C6—C1—C9—C8	−0.25 (13)
C7—O1—C3—C4	−173.81 (12)	C6—C1—C9—C11	175.68 (11)
C13—O3—C12—O2	2.08 (16)	C1—C2—C3—O1	179.49 (11)
C13—O3—C12—C11	−177.50 (9)	C1—C2—C3—C4	−0.15 (19)
C12—O3—C13—C14	171.98 (10)	O1—C3—C4—C5	−179.64 (13)
C8—N1—C6—C1	−2.16 (14)	C2—C3—C4—C5	0.0 (2)
C8—N1—C6—C5	177.77 (13)	C3—C4—C5—C6	0.3 (2)
C6—N1—C8—C9	2.03 (14)	C4—C5—C6—N1	179.64 (13)
C6—N1—C8—C10	−176.93 (11)	C4—C5—C6—C1	−0.4 (2)
C6—C1—C2—C3	−0.02 (17)	N1—C8—C9—C1	−1.07 (13)
C9—C1—C2—C3	178.39 (13)	N1—C8—C9—C11	−176.98 (11)
C2—C1—C6—N1	−179.74 (11)	C10—C8—C9—C1	177.77 (12)
C2—C1—C6—C5	0.33 (18)	C10—C8—C9—C11	1.9 (2)
C9—C1—C6—N1	1.47 (13)	C1—C9—C11—C12	117.42 (13)
C9—C1—C6—C5	−178.47 (12)	C8—C9—C11—C12	−67.42 (15)
C2—C1—C9—C8	−178.81 (13)	C9—C11—C12—O2	−69.51 (15)
C2—C1—C9—C11	−2.9 (2)	C9—C11—C12—O3	110.07 (11)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	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—H7A···Cg1^iv	0.98	2.99	3.9550 (16)	169

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₇NO₃
M_r	247.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	7.8117 (5), 17.1953 (12), 9.9003 (7)
β (°)	106.756 (1)
V (Å³)	1273.39 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.23 × 0.21 × 0.06

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2013)
T_min, T_max	0.84, 1.00
No. of measured, independent and observed [I > 2σ(I)] reflections	22947, 3374, 2889
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.117, 1.08
No. of reflections	3374
No. of parameters	170
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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—H7A···Cg1^iv	0.98	2.99	3.9550 (16)	169

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

Acknowledgements

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

References

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Volume 69| Part 8| August 2013| Page o1242

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