Dimethyl 8-acetyl-2-methyl-1,2-dihydro­quinoline-2,4-dicarboxyl­ate

Keleşoğlu, Z.; Gültekin, Z.; Büyükgüngör, O.

doi:10.1107/S1600536811003564

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Pages o544-o545

doi:10.1107/S1600536811003564

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Dimethyl 8-acetyl-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate

Zeynep Keleşoğlu,^a Zeynep Gültekin ^b and Orhan Büyükgüngör ^a ^*

^aDepartment of Physics, Ondokuz Mayıs University, TR-55139 Samsun, Turkey, and ^bDepartment of Chemistry, Çankırı Karatekin University, TR-18100 Çankırı, Turkey
^*Correspondence e-mail: orhanb@omu.edu.tr

(Received 19 January 2011; accepted 27 January 2011; online 2 February 2011)

In the title compound, C₁₆H₁₇NO₅, the six-membered N-containing ring has a half-boat form; the spiro C atom deviates by 0.34 (2) Å from the plane (r.m.s. deviation = 0.051 Å) defined by the N and four aromatic C atoms. Intramolecular N—H⋯O hydrogen bonding generates an S(6) ring motif and the dihedral angle between the mean plane though the S(6) ring and that through the five-atom half-boat plane is 3.39 (2)°. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link molecules into zigzag chains along [001] due to c-glide symmetry, and C—H⋯π interactions extend along [010].

Related literature

For the preparation of 1,2-dihydroquinoline, see: Dauphinee & Forrest (1978 ); Katritzky et al. (1996 ); Elmore et al. (2001 ); Lu & Malinakova (2004 ); Wang et al. (2009 ); Rezgui et al. (1999 ). For related structures, see: Yadav et al. (2007 ); Kamakshi & Reddy (2007 ); Kim et al. (2001 ); Sundèn et al. (2007 ); Waldmann et al. (2008 ). For ring puckering analysis, see: Cremer & Pople (1975 ). For graph-set theory, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₇NO₅
M_r = 303.31
Monoclinic, P 2₁ /c
a = 8.0222 (3) Å
b = 18.2466 (9) Å
c = 10.3478 (4) Å
β = 101.042 (3)°
V = 1486.65 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.74 × 0.43 × 0.23 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.823, T_max = 0.968
14613 measured reflections
3068 independent reflections
2221 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.169
S = 1.07
14613 reflections
205 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.36 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⋯O1	0.86 (2)	1.95 (2)	2.650 (2)	138 (2)
C10—H10⋯O3ⁱ	0.93	2.59	3.517 (3)	174
C14—H14C⋯Cg1ⁱ	0.96	2.89	3.692 (3)	142
C8—H8B⋯Cg1ⁱⁱ	0.96	2.85	3.501 (3)	126
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811003564/si2329sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811003564/si2329Isup2.hkl

checkCIF report

Comment top

Dihydroquinoline moiety is found in a wide variety of natural products and they have attracted a lot of attention from synthetic organic chemists (Kamakshi & Reddy, 2007). 1,2-Dihydroquinolines have received substantial attention due to their potential biological activities arising from their antioxidative properties as well as their usefulness as precursors of some other biologically active compounds (Kim et al., 2001). 1,2-Dihydroquinoline derivatives are known to exhibit a wide spectrum of biological activities such as antimalarial, antibacterial and anti-inflammatory behavior (Yadav et al., 2007).

Asymmetric synthesis of 1,2-dihydroquinolin have been attracted in recent years (Wang et al., 2009; Rezgui et al., 1999). Sundèn and co-worker has reported asymmetric synthesis of 1,2-dihydroquinolines using Domino reactions between 2-aminobenzaldehyde and α,β-unsaturated aldehydes to give pharmaceutically valuable 1,2-dihydroquinolines in high enantioselectivity (Sundèn et al., 2007). 1,2-dihydroquinolines was used for several applications, such as synthesis of quinolines: (Dauphinee & Forrest, 1978; Lu & Malinakova, 2004), 1,2,3,4- tetrahydroquinolines: (Katritzky et al., 1996) and natural products: (Elmore et al., 2001).

The molecule of the title compound contains dihydroquinoline, two methoxycarbonyl (O=C—O—CH₃) and acetyl group (O=C—CH₃). The two –CO₂Me groups are antisymmetric with respect to atom C10 (Fig. 1).

The six-membered N containing ring of the quinoline system displays a half-boat conformation with the puckering parameters of Q_T=0.261 (2) Å, Φ=146.7 (6)° and Θ=112.7 (4) ° (Cremer & Pople, 1975) and the spiro carbon atom deviates 0.34 (2) Å from the plane (r.m.s. deviation 0.051 Å) defined by the N1 and C1, C6, C9, C10 atoms. The intramolecular N—H..O hydrogen bond generate S(6) ring motif (Bernstein et al., 1995) (Fig. 1, Table 1). The dihedral angle between the S(6) ring mean plane and the half-boat plane of five atoms is 3.39 (2)°.

The crystal packing is stabilized by C10—H10···O3ⁱ intermolecular hydrogen bonds linking the molecules into chains in a zigzag mode along [0 0 1] due to c-glide symmetry, and there are also two C—H···π interactions C14—H14c···Cg1ⁱ and C8—H8b···Cg1ⁱⁱ [(i): x,1/2 - y,-1/2 + z; (ii):1 - x,1 - y,1 - z] extending along the b axis (Fig. 2., Table 1.).

Related literature top

For the preparation of 1,2-dihydroquinoline, see: Dauphinee & Forrest (1978); Katritzky et al. (1996); Elmore et al. (2001); Lu & Malinakova (2004); Wang et al. (2009); Rezgui et al. (1999). For related structures, see: Yadav et al. (2007); Kamakshi & Reddy (2007); Kim et al. (2001); Sundèn et al. (2007); Waldmann et al. (2008). For ring puckering analysis, see: Cremer & Pople (1975). For graph-set theory, see: Bernstein et al. (1995).

Experimental top

The title compound was synthesized after a method described by Waldmann et al., (2008). 2'-aminoacetophenone (100 mg, 1 eq) was dissolved in acetonitrile (1.5 ml) in a screw-capped test tube and Bi(OTf)₃ (5 mol %, 0.05 eq) was added to the mixture. This mixture were stirred at room temperature for 4 days until the starting material was completely consumed as monitored by TLC. The resultant residue was directly purified by flash chromatography on silica (EtOAc: Cyclohexane 2:98) gave 27% yield as a yellow solid. Recrystallized over pentan and ethyl acetate gave yellow crystalline solid. R_f 0.5 (2:1 Cyclohexane/EtOAc); m.p: (374–375 K).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); 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: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. An ORTEP view of (I), with the atom-numbering scheme and 30% probability displacement ellipsoids. Dashed lines indicate H-bonds.
	Fig. 2. A packing diagram for (I), showing the C—H···O hydrogen bonds and C—H···π interactions. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity. [Symmetry code; (i): x,1/2 - y,-1/2 + z; (ii): 1 - x,1 - y,1 - z]. (Cg1 is the centroid of the C1—C6 ring).

Dimethyl 8-acetyl-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate top

Crystal data top

C₁₆H₁₇NO₅	F(000) = 640
M_r = 303.31	D_x = 1.355 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14613 reflections
a = 8.0222 (3) Å	θ = 2.0–28.0°
b = 18.2466 (9) Å	µ = 0.10 mm⁻¹
c = 10.3478 (4) Å	T = 296 K
β = 101.042 (3)°	Prism, brown
V = 1486.65 (11) Å³	0.74 × 0.43 × 0.23 mm
Z = 4

Data collection top

Stoe IPDS 2 diffractometer	3068 independent reflections
Radiation source: fine-focus sealed tube	2221 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
rotation method scans	θ_max = 26.5°, θ_min = 2.2°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −10→10
T_min = 0.823, T_max = 0.968	k = −22→22
14613 measured reflections	l = −12→12

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0846P)² + 0.2827P] where P = (F_o² + 2F_c²)/3
14613 reflections	(Δ/σ)_max < 0.001
205 parameters	Δρ_max = 0.43 e Å⁻³
1 restraint	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₆H₁₇NO₅	V = 1486.65 (11) Å³
M_r = 303.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.0222 (3) Å	µ = 0.10 mm⁻¹
b = 18.2466 (9) Å	T = 296 K
c = 10.3478 (4) Å	0.74 × 0.43 × 0.23 mm
β = 101.042 (3)°

Data collection top

Stoe IPDS 2 diffractometer	3068 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2221 reflections with I > 2σ(I)
T_min = 0.823, T_max = 0.968	R_int = 0.055
14613 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	1 restraint
wR(F²) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.43 e Å⁻³
14613 reflections	Δρ_min = −0.36 e Å⁻³
205 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
C1	0.4104 (2)	0.37012 (12)	0.3615 (2)	0.0427 (5)
C2	0.5203 (3)	0.39441 (12)	0.4782 (2)	0.0458 (5)
C3	0.4559 (3)	0.39964 (14)	0.5939 (2)	0.0537 (6)
H3	0.5267	0.4161	0.6702	0.064*
C4	0.2911 (3)	0.38117 (16)	0.5987 (2)	0.0582 (6)
H4	0.2512	0.3853	0.6771	0.070*
C5	0.1846 (3)	0.35628 (15)	0.4853 (2)	0.0529 (6)
H5	0.0732	0.3436	0.4887	0.064*
C6	0.2403 (2)	0.34998 (13)	0.3675 (2)	0.0436 (5)
C7	0.6980 (3)	0.41517 (14)	0.4779 (2)	0.0507 (6)
C8	0.8065 (3)	0.44802 (16)	0.5984 (3)	0.0618 (7)
H8A	0.8402	0.4104	0.6630	0.074*
H8B	0.7431	0.4850	0.6341	0.074*
H8C	0.9058	0.4697	0.5751	0.074*
C9	0.1341 (2)	0.32351 (13)	0.2442 (2)	0.0454 (5)
C10	0.1863 (3)	0.32944 (14)	0.1302 (2)	0.0491 (5)
H10	0.1169	0.3113	0.0547	0.059*
C11	0.3514 (3)	0.36395 (13)	0.1178 (2)	0.0462 (5)
C12	−0.0356 (3)	0.28883 (15)	0.2385 (2)	0.0521 (6)
C13	−0.2120 (3)	0.21400 (18)	0.3394 (3)	0.0732 (8)
H13A	−0.2844	0.2489	0.3708	0.088*
H13B	−0.1979	0.1719	0.3960	0.088*
H13C	−0.2625	0.1993	0.2515	0.088*
C14	0.4362 (3)	0.32316 (16)	0.0183 (2)	0.0572 (6)
H14A	0.5410	0.3470	0.0119	0.069*
H14B	0.3620	0.3234	−0.0663	0.069*
H14C	0.4588	0.2735	0.0469	0.069*
C15	0.3165 (3)	0.44329 (14)	0.0688 (2)	0.0496 (6)
C16	0.1661 (4)	0.51590 (18)	−0.1039 (3)	0.0788 (9)
H16A	0.1176	0.5463	−0.0450	0.095*
H16B	0.0861	0.5102	−0.1851	0.095*
H16C	0.2678	0.5384	−0.1211	0.095*
N1	0.4639 (2)	0.36371 (12)	0.24524 (18)	0.0508 (5)
O1	0.7624 (2)	0.40668 (13)	0.38037 (19)	0.0708 (6)
O2	−0.1528 (2)	0.29932 (15)	0.1485 (2)	0.0906 (8)
O3	−0.0469 (2)	0.24724 (11)	0.33918 (18)	0.0657 (5)
O4	0.3796 (3)	0.49676 (12)	0.1243 (2)	0.0794 (6)
O5	0.2062 (2)	0.44499 (10)	−0.04465 (18)	0.0641 (5)
H1	0.566 (2)	0.3785 (15)	0.248 (3)	0.065 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0390 (10)	0.0448 (12)	0.0419 (11)	0.0046 (9)	0.0017 (8)	0.0007 (9)
C2	0.0438 (11)	0.0449 (12)	0.0450 (12)	0.0039 (9)	−0.0014 (9)	0.0003 (10)
C3	0.0524 (12)	0.0619 (16)	0.0425 (12)	−0.0001 (11)	−0.0015 (10)	−0.0073 (11)
C4	0.0540 (13)	0.0755 (18)	0.0454 (13)	0.0000 (12)	0.0099 (10)	−0.0068 (12)
C5	0.0463 (11)	0.0635 (15)	0.0486 (13)	0.0016 (10)	0.0081 (10)	−0.0037 (11)
C6	0.0397 (10)	0.0455 (12)	0.0431 (12)	0.0025 (8)	0.0018 (8)	−0.0009 (9)
C7	0.0441 (11)	0.0536 (14)	0.0507 (14)	0.0021 (10)	−0.0005 (10)	−0.0018 (11)
C8	0.0503 (12)	0.0684 (17)	0.0611 (16)	−0.0086 (11)	−0.0031 (11)	−0.0069 (13)
C9	0.0392 (10)	0.0497 (13)	0.0446 (12)	0.0008 (9)	0.0013 (9)	0.0021 (10)
C10	0.0422 (10)	0.0575 (14)	0.0440 (12)	−0.0040 (10)	−0.0007 (9)	−0.0034 (10)
C11	0.0407 (10)	0.0574 (14)	0.0391 (11)	−0.0018 (9)	0.0041 (8)	−0.0030 (10)
C12	0.0461 (12)	0.0657 (16)	0.0424 (12)	−0.0063 (10)	0.0027 (10)	−0.0011 (11)
C13	0.0639 (15)	0.086 (2)	0.0689 (18)	−0.0292 (15)	0.0113 (13)	0.0083 (16)
C14	0.0509 (12)	0.0676 (17)	0.0534 (15)	0.0019 (11)	0.0108 (10)	−0.0106 (12)
C15	0.0463 (11)	0.0599 (15)	0.0428 (12)	−0.0056 (10)	0.0095 (9)	−0.0046 (11)
C16	0.0801 (19)	0.077 (2)	0.074 (2)	0.0029 (16)	0.0012 (15)	0.0221 (17)
N1	0.0375 (9)	0.0726 (14)	0.0405 (10)	−0.0042 (9)	0.0032 (8)	−0.0029 (9)
O1	0.0446 (9)	0.1052 (16)	0.0605 (11)	−0.0100 (9)	0.0051 (8)	−0.0129 (11)
O2	0.0528 (10)	0.149 (2)	0.0624 (12)	−0.0263 (11)	−0.0078 (9)	0.0270 (13)
O3	0.0573 (9)	0.0731 (13)	0.0615 (11)	−0.0174 (8)	−0.0020 (8)	0.0178 (10)
O4	0.1003 (15)	0.0624 (12)	0.0673 (13)	−0.0137 (11)	−0.0043 (11)	−0.0087 (10)
O5	0.0648 (10)	0.0631 (12)	0.0566 (11)	−0.0039 (8)	−0.0079 (8)	0.0080 (9)

Geometric parameters (Å, º) top

C1—N1	1.358 (3)	C10—H10	0.9300
C1—C2	1.423 (3)	C11—N1	1.448 (3)
C1—C6	1.426 (3)	C11—C14	1.531 (3)
C2—C3	1.395 (3)	C11—C15	1.542 (3)
C2—C7	1.475 (3)	C12—O2	1.205 (3)
C3—C4	1.374 (3)	C12—O3	1.306 (3)
C3—H3	0.9300	C13—O3	1.457 (3)
C4—C5	1.389 (3)	C13—H13A	0.9600
C4—H4	0.9300	C13—H13B	0.9600
C5—C6	1.381 (3)	C13—H13C	0.9600
C5—H5	0.9300	C14—H14A	0.9600
C6—C9	1.474 (3)	C14—H14B	0.9600
C7—O1	1.229 (3)	C14—H14C	0.9600
C7—C8	1.502 (3)	C15—O4	1.195 (3)
C8—H8A	0.9600	C15—O5	1.328 (3)
C8—H8B	0.9600	C16—O5	1.442 (3)
C8—H8C	0.9600	C16—H16A	0.9600
C9—C10	1.330 (3)	C16—H16B	0.9600
C9—C12	1.492 (3)	C16—H16C	0.9600
C10—C11	1.494 (3)	N1—H1	0.858 (17)

N1—C1—C2	121.97 (18)	N1—C11—C14	109.33 (18)
N1—C1—C6	118.91 (19)	C10—C11—C14	111.6 (2)
C2—C1—C6	119.11 (19)	N1—C11—C15	110.15 (19)
C3—C2—C1	118.56 (19)	C10—C11—C15	108.43 (18)
C3—C2—C7	120.1 (2)	C14—C11—C15	108.15 (19)
C1—C2—C7	121.3 (2)	O2—C12—O3	123.1 (2)
C4—C3—C2	122.1 (2)	O2—C12—C9	122.3 (2)
C4—C3—H3	118.9	O3—C12—C9	114.68 (19)
C2—C3—H3	118.9	O3—C13—H13A	109.5
C3—C4—C5	119.3 (2)	O3—C13—H13B	109.5
C3—C4—H4	120.3	H13A—C13—H13B	109.5
C5—C4—H4	120.3	O3—C13—H13C	109.5
C6—C5—C4	121.5 (2)	H13A—C13—H13C	109.5
C6—C5—H5	119.3	H13B—C13—H13C	109.5
C4—C5—H5	119.3	C11—C14—H14A	109.5
C5—C6—C1	119.4 (2)	C11—C14—H14B	109.5
C5—C6—C9	124.05 (19)	H14A—C14—H14B	109.5
C1—C6—C9	116.55 (19)	C11—C14—H14C	109.5
O1—C7—C2	121.9 (2)	H14A—C14—H14C	109.5
O1—C7—C8	117.6 (2)	H14B—C14—H14C	109.5
C2—C7—C8	120.5 (2)	O4—C15—O5	123.7 (2)
C7—C8—H8A	109.5	O4—C15—C11	125.1 (2)
C7—C8—H8B	109.5	O5—C15—C11	111.1 (2)
H8A—C8—H8B	109.5	O5—C16—H16A	109.5
C7—C8—H8C	109.5	O5—C16—H16B	109.5
H8A—C8—H8C	109.5	H16A—C16—H16B	109.5
H8B—C8—H8C	109.5	O5—C16—H16C	109.5
C10—C9—C6	120.85 (19)	H16A—C16—H16C	109.5
C10—C9—C12	116.1 (2)	H16B—C16—H16C	109.5
C6—C9—C12	123.04 (19)	C1—N1—C11	124.00 (17)
C9—C10—C11	123.1 (2)	C1—N1—H1	114.2 (19)
C9—C10—H10	118.5	C11—N1—H1	116.7 (19)
C11—C10—H10	118.5	C12—O3—C13	116.44 (19)
N1—C11—C10	109.17 (18)	C15—O5—C16	117.0 (2)

N1—C1—C2—C3	179.9 (2)	C12—C9—C10—C11	178.9 (2)
C6—C1—C2—C3	−1.8 (3)	C9—C10—C11—N1	20.8 (3)
N1—C1—C2—C7	1.1 (3)	C9—C10—C11—C14	141.8 (2)
C6—C1—C2—C7	179.3 (2)	C9—C10—C11—C15	−99.2 (3)
C1—C2—C3—C4	0.9 (4)	C10—C9—C12—O2	−37.6 (4)
C7—C2—C3—C4	179.8 (2)	C6—C9—C12—O2	142.5 (3)
C2—C3—C4—C5	0.2 (4)	C10—C9—C12—O3	143.2 (2)
C3—C4—C5—C6	−0.3 (4)	C6—C9—C12—O3	−36.7 (3)
C4—C5—C6—C1	−0.6 (4)	N1—C11—C15—O4	3.5 (3)
C4—C5—C6—C9	179.6 (2)	C10—C11—C15—O4	122.9 (3)
N1—C1—C6—C5	180.0 (2)	C14—C11—C15—O4	−115.9 (3)
C2—C1—C6—C5	1.7 (3)	N1—C11—C15—O5	−176.59 (17)
N1—C1—C6—C9	−0.2 (3)	C10—C11—C15—O5	−57.2 (2)
C2—C1—C6—C9	−178.5 (2)	C14—C11—C15—O5	64.0 (2)
C3—C2—C7—O1	175.0 (3)	C2—C1—N1—C11	−158.1 (2)
C1—C2—C7—O1	−6.1 (4)	C6—C1—N1—C11	23.6 (3)
C3—C2—C7—C8	−5.2 (4)	C10—C11—N1—C1	−32.7 (3)
C1—C2—C7—C8	173.6 (2)	C14—C11—N1—C1	−155.0 (2)
C5—C6—C9—C10	169.4 (2)	C15—C11—N1—C1	86.3 (3)
C1—C6—C9—C10	−10.4 (3)	O2—C12—O3—C13	−0.9 (4)
C5—C6—C9—C12	−10.7 (4)	C9—C12—O3—C13	178.3 (2)
C1—C6—C9—C12	169.5 (2)	O4—C15—O5—C16	1.8 (4)
C6—C9—C10—C11	−1.3 (4)	C11—C15—O5—C16	−178.1 (2)

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···O1	0.86 (2)	1.95 (2)	2.650 (2)	138 (2)
C10—H10···O3ⁱ	0.93	2.59	3.517 (3)	174
C14—H14C···Cg1ⁱ	0.96	2.89	3.692 (3)	142
C8—H8B···Cg1ⁱⁱ	0.96	2.85	3.501 (3)	126

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇NO₅
M_r	303.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.0222 (3), 18.2466 (9), 10.3478 (4)
β (°)	101.042 (3)
V (Å³)	1486.65 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.74 × 0.43 × 0.23

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.823, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	14613, 3068, 2221
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.169, 1.07
No. of reflections	14613
No. of parameters	205
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.36

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

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···O1	0.858 (17)	1.95 (2)	2.650 (2)	138 (2)
C10—H10···O3ⁱ	0.93	2.59	3.517 (3)	174
C14—H14C···Cg1ⁱ	0.96	2.89	3.692 (3)	142
C8—H8B···Cg1ⁱⁱ	0.96	2.85	3.501 (3)	126

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

Acknowledgements

The title product was synthesized at RWTH Aachen University. The authors thank Professor Magnus Rueping of RWTH Aachen University, Germany, for helpful discussions and acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

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Volume 67| Part 3| March 2011| Pages o544-o545

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