Ethyl 2-{[2-(2-eth­oxy-2-oxoeth­oxy)quinolin-4-yl]carbon­yloxy}acetate

Bouzian, Y.; Hlimi, F.; Sebbar, N. kheira; El Hafi, M.; Hni, B.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314618014384

organic compounds

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ISSN: 2414-3146

Volume 3| Part 10| October 2018| x181438

https://doi.org/10.1107/S2414314618014384

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Ethyl 2-{[2-(2-ethoxy-2-oxoethoxy)quinolin-4-yl]carbonyloxy}acetate

Younos Bouzian,^a ^* Fouzia Hlimi,^a Nada kheira Sebbar,^a Mohamed El Hafi,^a Brahim Hni,^a El Mokhtar Essassi ^a and Joel T. Mague ^b

^aLaboratoire de Chimie Organique Hétérocyclique, Centre de Recherche Des Sciences des Médicaments, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, and ^bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: Bouzianyounes@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 9 October 2018; accepted 11 October 2018; online 16 October 2018)

The conformation of the 2-ethoxy-2-oxoethoxy side chain, including a gauche C_e—O—C—C₃ [72.46 (16)°] (e = ethoxy) unit, in the title compound, C₁₈H₁₉NO₇, is partly determined by an intramolecular C—H⋯O hydrogen bond. In the crystal, C—H⋯O hydrogen bonds and C—H⋯π interactions arising from the same methylene group form chains extending along the a-axis direction.

Keywords: crystal structure; quinoline; hydrogen bond; C—H⋯π.

CCDC reference: 1872739

Structure description

Quinoline derivatives have various biological properties including antibacterial (Kidwai et al., 2000 ) antiviral (Wathen et al., 2002 ), anticancer (Chen et al., 2013 ) and antimalarial (Kunin & Ellise, 2000 ) activity. As part of our studies in this area, we now describe the synthesis and structure of the title compound.

As expected, the quinoline core of the molecule is almost planar (r.m.s. deviation = 0.0149) with N1 deviating by the largest amount [0.0272 (9) Å]. The orientation of the inner portion of the side chain emanating from C7 is partially determined by an intramolecular C5—H5⋯O5 hydrogen bond (Fig. 1 and Table 1). In the crystal, the molecules form chains extending along the a-axis direction through a combination of C10—H10A⋯O2 hydrogen bonds and C10—H10B⋯Cg2 interactions (Table 1 and Fig. 2). The chains pack with intercalation of the shorter side chains on one side and the longer ones on the other and with the quinoline moieties alternately up and down from one chain to the next (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O5	0.977 (19)	2.244 (17)	2.8681 (17)	120.7 (14)
C10—H10A⋯O2ⁱ	0.954 (19)	2.435 (19)	3.3079 (16)	152.1 (15)
C10—H10B⋯Cg2ⁱ	0.983 (17)	3.249 (16)	4.0173 (14)	136.3 (15)
Symmetry code: (i) x+1, y, z.

Figure 1
The title molecule showing 50% probability ellipsoids. The intramolecular hydrogen bond is shown by a dashed line.

Figure 2
A portion of the hydrogen-bonded chain viewed along the b-axis direction. C—H⋯O hydrogen bonds and C—H⋯π(ring) interactions are shown, respectively, by black and green dashed lines.

Figure 3
Packing viewed along the b-axis direction with intermolecular interactions depicted as in Fig. 2

Synthesis and crystallization

A solution of 0.8 g (4.23 mmol) of 2-oxo-1,2-dihydroquinoline-4-carboxylic acid in 25 ml of DMF was mixed with 0.94 ml (8.46 mmol) ethyl bromoacetate, 1.17 g (8.46 mmol) K₂CO₃ and 0.13 g (0.423 mmol) tetra-n-butylammonium bromide (TBAB). The reaction mixture was stirred at room temperature in DMF for 24 h. After removal of salts by filtration, the DMF was evaporated under reduced pressure and the residue obtained was dissolved in dichloromethane. The organic phase was dried over Na₂SO₄ then concentrated in vacuo. The resulting mixture was chromatographed on a silica gel column [eluent: ethyl acetate/hexane (1/9)]. Colourless blocks were obtained when the solvent was allowed to evaporate (yield: 20%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₈H₁₉NO₇
M_r	361.34
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	150
a, b, c (Å)	4.9417 (2), 7.6157 (3), 23.4472 (9)
α, β, γ (°)	94.490 (2), 92.997 (2), 98.136 (2)
V (Å³)	869.06 (6)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	0.91
Crystal size (mm)	0.19 × 0.14 × 0.08

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.85, 0.93
No. of measured, independent and observed [I > 2σ(I)] reflections	6827, 3301, 2894
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.099, 1.03
No. of reflections	3301
No. of parameters	312
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.20
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL2018/1 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1872739

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314618014384/hb4265sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618014384/hb4265Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618014384/hb4265Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314618014384/hb4265Isup4.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Ethyl 2-{[2-(2-ethoxy-2-oxoethoxy)quinolin-4-yl]carbonyloxy}acetate top

Crystal data top

C₁₈H₁₉NO₇	Z = 2
M_r = 361.34	F(000) = 380
Triclinic, P1	D_x = 1.381 Mg m⁻³
a = 4.9417 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 7.6157 (3) Å	Cell parameters from 5397 reflections
c = 23.4472 (9) Å	θ = 3.8–74.5°
α = 94.490 (2)°	µ = 0.91 mm⁻¹
β = 92.997 (2)°	T = 150 K
γ = 98.136 (2)°	Block, colourless
V = 869.06 (6) Å³	0.19 × 0.14 × 0.08 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3301 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2894 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.023
Detector resolution: 10.4167 pixels mm^-1	θ_max = 74.5°, θ_min = 3.8°
ω scans	h = −5→6
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −9→9
T_min = 0.85, T_max = 0.93	l = −27→29
6827 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	All H-atom parameters refined
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.0479P)² + 0.2771P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3301 reflections	Δρ_max = 0.29 e Å⁻³
312 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/1 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0144 (10)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.9795 (2)	0.19616 (13)	0.19654 (4)	0.0298 (2)
O2	0.6525 (2)	0.10059 (14)	0.09687 (4)	0.0347 (3)
O3	0.9762 (2)	0.24142 (13)	0.04573 (4)	0.0314 (2)
O4	0.3329 (3)	0.15037 (15)	0.35154 (5)	0.0549 (4)
O5	0.3071 (2)	0.43440 (13)	0.37905 (4)	0.0317 (2)
O6	0.5808 (2)	0.31430 (16)	0.46977 (5)	0.0409 (3)
O7	0.1851 (2)	0.22790 (15)	0.50923 (4)	0.0370 (3)
N1	0.7797 (2)	0.45027 (15)	0.19139 (5)	0.0264 (3)
C1	0.6133 (3)	0.56258 (17)	0.21529 (5)	0.0253 (3)
C2	0.5848 (3)	0.71671 (19)	0.18733 (6)	0.0322 (3)
H2	0.691 (4)	0.735 (2)	0.1526 (8)	0.041 (5)*
C3	0.4194 (3)	0.83331 (19)	0.20776 (6)	0.0348 (3)
H3	0.403 (4)	0.937 (3)	0.1890 (8)	0.043 (5)*
C4	0.2734 (3)	0.80006 (19)	0.25639 (6)	0.0341 (3)
H4	0.157 (4)	0.883 (3)	0.2708 (8)	0.046 (5)*
C5	0.2999 (3)	0.65216 (19)	0.28472 (6)	0.0304 (3)
H5	0.198 (4)	0.632 (2)	0.3188 (8)	0.042 (5)*
C6	0.4736 (3)	0.53005 (17)	0.26569 (5)	0.0250 (3)
C7	0.5175 (3)	0.37093 (17)	0.29200 (5)	0.0258 (3)
C8	0.6876 (3)	0.26321 (18)	0.26838 (6)	0.0266 (3)
H8	0.720 (3)	0.155 (2)	0.2853 (7)	0.035 (4)*
C9	0.8144 (3)	0.31020 (17)	0.21775 (5)	0.0246 (3)
C10	1.0894 (3)	0.2362 (2)	0.14312 (6)	0.0291 (3)
H10A	1.229 (4)	0.163 (2)	0.1374 (7)	0.040 (5)*
H10B	1.164 (3)	0.363 (2)	0.1426 (7)	0.032 (4)*
C11	0.8761 (3)	0.18459 (17)	0.09398 (6)	0.0257 (3)
C12	0.7954 (3)	0.1969 (2)	−0.00618 (6)	0.0393 (4)
H12A	0.743 (4)	0.062 (3)	−0.0114 (8)	0.052 (5)*
H12B	0.632 (4)	0.253 (3)	−0.0010 (8)	0.052 (5)*
C13	0.9522 (4)	0.2659 (3)	−0.05472 (7)	0.0476 (4)
H13A	1.130 (5)	0.207 (3)	−0.0576 (10)	0.072 (7)*
H13B	0.832 (5)	0.235 (3)	−0.0907 (10)	0.070 (7)*
H13C	1.009 (5)	0.394 (3)	−0.0492 (10)	0.066 (6)*
C14	0.3772 (3)	0.30534 (19)	0.34306 (6)	0.0309 (3)
C15	0.1559 (3)	0.3732 (2)	0.42636 (6)	0.0339 (3)
H15A	0.005 (4)	0.282 (3)	0.4126 (8)	0.042 (5)*
H15B	0.094 (4)	0.479 (3)	0.4439 (8)	0.043 (5)*
C16	0.3364 (3)	0.30131 (18)	0.46988 (6)	0.0273 (3)
C17	0.3261 (3)	0.1532 (2)	0.55576 (7)	0.0376 (4)
H17A	0.341 (4)	0.031 (3)	0.5435 (8)	0.052 (5)*
H17B	0.506 (4)	0.219 (3)	0.5618 (8)	0.047 (5)*
C18	0.1607 (4)	0.1651 (2)	0.60672 (7)	0.0403 (4)
H18A	0.249 (4)	0.113 (3)	0.6388 (9)	0.058 (6)*
H18B	−0.019 (4)	0.104 (3)	0.5980 (8)	0.050 (5)*
H18C	0.158 (5)	0.296 (3)	0.6203 (10)	0.069 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0316 (5)	0.0373 (5)	0.0231 (5)	0.0121 (4)	0.0057 (4)	0.0030 (4)
O2	0.0276 (5)	0.0424 (6)	0.0325 (5)	0.0004 (4)	0.0062 (4)	−0.0021 (4)
O3	0.0311 (5)	0.0395 (5)	0.0225 (5)	0.0015 (4)	0.0016 (4)	0.0026 (4)
O4	0.0931 (10)	0.0301 (6)	0.0388 (6)	−0.0094 (6)	0.0309 (6)	0.0011 (5)
O5	0.0359 (5)	0.0364 (5)	0.0256 (5)	0.0087 (4)	0.0141 (4)	0.0053 (4)
O6	0.0265 (5)	0.0575 (7)	0.0419 (6)	0.0097 (5)	0.0125 (4)	0.0108 (5)
O7	0.0269 (5)	0.0550 (7)	0.0322 (5)	0.0067 (4)	0.0076 (4)	0.0185 (5)
N1	0.0264 (5)	0.0309 (6)	0.0215 (5)	0.0026 (4)	0.0019 (4)	0.0021 (4)
C1	0.0249 (6)	0.0277 (6)	0.0218 (6)	0.0015 (5)	−0.0017 (5)	−0.0010 (5)
C2	0.0378 (8)	0.0332 (7)	0.0250 (7)	0.0013 (6)	0.0016 (6)	0.0061 (5)
C3	0.0440 (8)	0.0274 (7)	0.0322 (7)	0.0055 (6)	−0.0067 (6)	0.0039 (6)
C4	0.0369 (8)	0.0305 (7)	0.0339 (8)	0.0089 (6)	−0.0044 (6)	−0.0055 (6)
C5	0.0320 (7)	0.0331 (7)	0.0251 (7)	0.0032 (6)	0.0034 (6)	−0.0029 (5)
C6	0.0250 (6)	0.0261 (6)	0.0217 (6)	−0.0002 (5)	−0.0021 (5)	−0.0012 (5)
C7	0.0268 (6)	0.0278 (6)	0.0208 (6)	−0.0018 (5)	0.0019 (5)	−0.0007 (5)
C8	0.0310 (7)	0.0269 (6)	0.0213 (6)	0.0029 (5)	0.0011 (5)	0.0018 (5)
C9	0.0240 (6)	0.0292 (6)	0.0199 (6)	0.0033 (5)	−0.0001 (5)	−0.0004 (5)
C10	0.0245 (6)	0.0410 (8)	0.0230 (7)	0.0074 (6)	0.0057 (5)	0.0016 (5)
C11	0.0250 (6)	0.0275 (6)	0.0257 (7)	0.0079 (5)	0.0057 (5)	−0.0006 (5)
C12	0.0373 (8)	0.0537 (10)	0.0257 (7)	0.0070 (7)	−0.0040 (6)	−0.0009 (6)
C13	0.0662 (12)	0.0509 (10)	0.0253 (8)	0.0065 (9)	0.0009 (8)	0.0049 (7)
C14	0.0345 (7)	0.0309 (7)	0.0253 (7)	−0.0017 (6)	0.0064 (6)	−0.0013 (5)
C15	0.0299 (7)	0.0479 (9)	0.0264 (7)	0.0073 (6)	0.0128 (6)	0.0094 (6)
C16	0.0268 (7)	0.0290 (6)	0.0267 (7)	0.0046 (5)	0.0094 (5)	0.0001 (5)
C17	0.0367 (8)	0.0459 (9)	0.0349 (8)	0.0153 (7)	0.0064 (6)	0.0138 (7)
C18	0.0368 (8)	0.0522 (10)	0.0323 (8)	0.0047 (7)	0.0024 (7)	0.0097 (7)

Geometric parameters (Å, º) top

O1—C9	1.3577 (15)	C6—C7	1.4401 (19)
O1—C10	1.4285 (16)	C7—C8	1.3633 (19)
O2—C11	1.2036 (17)	C7—C14	1.4988 (19)
O3—C11	1.3367 (16)	C8—C9	1.4180 (18)
O3—C12	1.4598 (17)	C8—H8	0.972 (18)
O4—C14	1.2035 (19)	C10—C11	1.5092 (19)
O5—C14	1.3399 (17)	C10—H10A	0.954 (19)
O5—C15	1.4405 (16)	C10—H10B	0.983 (17)
O6—C16	1.1978 (17)	C12—C13	1.498 (2)
O7—C16	1.3259 (17)	C12—H12A	1.02 (2)
O7—C17	1.4593 (18)	C12—H12B	0.97 (2)
N1—C9	1.3012 (17)	C13—H13A	1.05 (2)
N1—C1	1.3762 (17)	C13—H13B	1.00 (2)
C1—C2	1.4090 (19)	C13—H13C	0.97 (2)
C1—C6	1.4201 (19)	C15—C16	1.506 (2)
C2—C3	1.366 (2)	C15—H15A	0.96 (2)
C2—H2	1.001 (18)	C15—H15B	0.97 (2)
C3—C4	1.402 (2)	C17—C18	1.486 (2)
C3—H3	0.943 (19)	C17—H17A	0.97 (2)
C4—C5	1.370 (2)	C17—H17B	0.95 (2)
C4—H4	0.966 (19)	C18—H18A	0.99 (2)
C5—C6	1.4152 (19)	C18—H18B	0.95 (2)
C5—H5	0.978 (19)	C18—H18C	1.03 (3)

C9—O1—C10	115.23 (10)	O2—C11—C10	125.79 (12)
C11—O3—C12	116.03 (11)	O3—C11—C10	109.56 (11)
C14—O5—C15	115.02 (11)	O3—C12—C13	106.86 (13)
C16—O7—C17	117.59 (11)	O3—C12—H12A	108.1 (11)
C9—N1—C1	117.42 (11)	C13—C12—H12A	111.8 (11)
N1—C1—C2	116.81 (12)	O3—C12—H12B	108.2 (12)
N1—C1—C6	123.38 (12)	C13—C12—H12B	112.1 (12)
C2—C1—C6	119.81 (12)	H12A—C12—H12B	109.6 (16)
C3—C2—C1	120.40 (13)	C12—C13—H13A	109.5 (13)
C3—C2—H2	123.1 (10)	C12—C13—H13B	108.0 (13)
C1—C2—H2	116.5 (10)	H13A—C13—H13B	110.2 (18)
C2—C3—C4	120.43 (13)	C12—C13—H13C	112.1 (13)
C2—C3—H3	119.8 (11)	H13A—C13—H13C	107.2 (19)
C4—C3—H3	119.7 (11)	H13B—C13—H13C	109.8 (19)
C5—C4—C3	120.31 (13)	O4—C14—O5	122.56 (13)
C5—C4—H4	119.4 (11)	O4—C14—C7	123.18 (13)
C3—C4—H4	120.3 (11)	O5—C14—C7	114.25 (12)
C4—C5—C6	121.04 (13)	O5—C15—C16	111.47 (11)
C4—C5—H5	118.9 (11)	O5—C15—H15A	110.1 (11)
C6—C5—H5	120.0 (11)	C16—C15—H15A	109.7 (11)
C5—C6—C1	117.97 (12)	O5—C15—H15B	104.6 (11)
C5—C6—C7	125.85 (12)	C16—C15—H15B	108.7 (11)
C1—C6—C7	116.16 (12)	H15A—C15—H15B	112.2 (15)
C8—C7—C6	119.62 (12)	O6—C16—O7	125.43 (13)
C8—C7—C14	115.35 (12)	O6—C16—C15	124.80 (13)
C6—C7—C14	124.95 (12)	O7—C16—C15	109.73 (11)
C7—C8—C9	118.76 (12)	O7—C17—C18	107.62 (12)
C7—C8—H8	121.0 (10)	O7—C17—H17A	108.0 (12)
C9—C8—H8	120.2 (10)	C18—C17—H17A	111.4 (12)
N1—C9—O1	119.94 (11)	O7—C17—H17B	107.5 (12)
N1—C9—C8	124.63 (12)	C18—C17—H17B	113.4 (12)
O1—C9—C8	115.43 (11)	H17A—C17—H17B	108.7 (16)
O1—C10—C11	111.20 (11)	C17—C18—H18A	109.5 (12)
O1—C10—H10A	106.4 (11)	C17—C18—H18B	110.4 (12)
C11—C10—H10A	107.0 (11)	H18A—C18—H18B	109.9 (17)
O1—C10—H10B	112.6 (9)	C17—C18—H18C	109.8 (13)
C11—C10—H10B	109.0 (10)	H18A—C18—H18C	106.2 (18)
H10A—C10—H10B	110.5 (15)	H18B—C18—H18C	111.0 (17)
O2—C11—O3	124.61 (12)

C9—N1—C1—C2	177.99 (12)	C10—O1—C9—C8	175.21 (11)
C9—N1—C1—C6	−1.91 (18)	C7—C8—C9—N1	−0.3 (2)
N1—C1—C2—C3	178.82 (13)	C7—C8—C9—O1	−179.63 (11)
C6—C1—C2—C3	−1.3 (2)	C9—O1—C10—C11	−76.01 (14)
C1—C2—C3—C4	−0.8 (2)	C12—O3—C11—O2	0.38 (19)
C2—C3—C4—C5	1.5 (2)	C12—O3—C11—C10	178.34 (12)
C3—C4—C5—C6	−0.1 (2)	O1—C10—C11—O2	−8.81 (19)
C4—C5—C6—C1	−1.89 (19)	O1—C10—C11—O3	173.25 (10)
C4—C5—C6—C7	179.92 (12)	C11—O3—C12—C13	−177.61 (13)
N1—C1—C6—C5	−177.54 (12)	C15—O5—C14—O4	−4.6 (2)
C2—C1—C6—C5	2.56 (18)	C15—O5—C14—C7	176.06 (11)
N1—C1—C6—C7	0.83 (18)	C8—C7—C14—O4	−25.5 (2)
C2—C1—C6—C7	−179.08 (12)	C6—C7—C14—O4	151.15 (16)
C5—C6—C7—C8	178.79 (12)	C8—C7—C14—O5	153.84 (12)
C1—C6—C7—C8	0.57 (18)	C6—C7—C14—O5	−29.51 (19)
C5—C6—C7—C14	2.3 (2)	C14—O5—C15—C16	72.46 (16)
C1—C6—C7—C14	−175.94 (12)	C17—O7—C16—O6	−1.3 (2)
C6—C7—C8—C9	−0.84 (19)	C17—O7—C16—C15	−178.99 (13)
C14—C7—C8—C9	175.99 (11)	O5—C15—C16—O6	9.4 (2)
C1—N1—C9—O1	−179.05 (11)	O5—C15—C16—O7	−172.89 (12)
C1—N1—C9—C8	1.65 (19)	C16—O7—C17—C18	151.56 (14)
C10—O1—C9—N1	−4.16 (17)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O5	0.977 (19)	2.244 (17)	2.8681 (17)	120.7 (14)
C10—H10A···O2ⁱ	0.954 (19)	2.435 (19)	3.3079 (16)	152.1 (15)
C10—H10B···Cg2ⁱ	0.983 (17)	3.249 (16)	4.0173 (14)	136.3 (15)

Symmetry code: (i) x+1, y, z.

Funding information

The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

Brandenburg, K. & Putz, H. (2012). DIAMOND, Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Chen, H., Yang, Z., Ding, C., Chu, L., Zhang, Y., Terry, K., Liu, H., Shen, Q. & Zhou, J. (2013). Eur. J. Med. Chem. 62, 498–507. Web of Science CrossRef PubMed Google Scholar
Kidwai, M., Bhushan, K., Sapra, P., Saxena, R. & Gupta, R. (2000). Bioorg. Med. Chem. 8, 69–72. Web of Science CrossRef PubMed CAS Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Kunin, C. M. & Ellis, W. Y. (2000). Antimicrob. Agents Chemother. 44, 848–852. Web of Science CrossRef PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Wathen, M. W. (2002). Rev. Med. Virol. 12, 167–178. Web of Science CrossRef PubMed Google Scholar

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