9-(2-Hy­droxy-6-oxocyclo­hex-1-en-1-yl)-2,3,4,9-tetra­hydro-1H-xanthen-1-one

Mohamed, S.K.; Akkurt, M.; Abdelhamid, A.A.; Saeed, A.; Flörke, U.

doi:10.1107/S1600536813007952

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Pages o616-o617

doi:10.1107/S1600536813007952

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9-(2-Hydroxy-6-oxocyclohex-1-en-1-yl)-2,3,4,9-tetrahydro-1H-xanthen-1-one

Shaaban K. Mohamed,^a ^* Mehmet Akkurt,^b Antar A. Abdelhamid,^a Aamer Saeed ^c and Ulrich Flörke ^d

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^dDepartment Chemie, Fakultät für Naturwissenschaften, Universität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany
^*Correspondence e-mail: shaabankamel@yahoo.com_and_akkurt@erciyes.edu.tr

(Received 22 February 2013; accepted 22 March 2013; online 28 March 2013)

In the xanthene ring system in the title compound, C₁₉H₁₈O₄, the 4H-pyran ring has a maximum deviation of 0.110 (2) Å from planarity and the cyclohexene ring exhibits a puckered conformation [puckering parameters Q_T = 0.452 (3) Å, θ = 57.0 (4) and φ = 131.7 (4)°]. The cyclohexene ring attached to the xanthene system adopts an envelope conformation, with the middle of the three methylene C atoms as the flap atom. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds form infinite chains of R₁²(6) ring motifs along [100] with the xanthene groups arranged in an alternating zigzag manner.

Related literature

For the bioactivity of xanthene compounds, see: Mohamed et al. (2012a ); Mo et al. (2010 ) and for their fluorescence properties, see: Menchen et al. (2003 ). For similar structures see: Mohamed et al. (2011 , 2012b ); Kurbanova et al. (2012 ); Abdelhamid et al. (2011 ); Reddy et al. (2009 ). For ring conformations, see: Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₉H₁₈O₄
M_r = 310.33
Orthorhombic, P n a 2₁
a = 13.4420 (18) Å
b = 8.0015 (10) Å
c = 14.2416 (18) Å
V = 1531.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 130 K
0.37 × 0.24 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.966, T_max = 0.986
13880 measured reflections
1901 independent reflections
1799 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.111
S = 1.06
1901 reflections
209 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.84	1.76	2.582 (2)	164
C5—H5A⋯O1ⁱ	0.99	2.42	3.034 (3)	119
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 2012 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813007952/nk2202sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813007952/nk2202Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813007952/nk2202Isup3.cml

checkCIF report

Comment top

Due to the great spectroscopic and biological applications of xanthene molecules, they attracted an excessive interest of researchers in different fields of medicinal and applied chemistry. Such derivatives have exhibited fluorescence properties (Menchen et al., 2003) in addition to their fungicidal, bactericidal and anti-inflammatory possessions (Mohamed et al., 2012a; Mo et al., 2010). As part of our on-going study on synthesis of potential biologically active molecules based xanthene core structure compounds, herein we report the synthesis and structural study of the title compound.

The title compound (I) is shown in Fig. 1. In the xanthene ring system (O3/C7–C19) of (I), the 4H-pyran ring (O3/C7/C8/C13/C14/C19) is nearly planar [maximum deviation = 0.110 (2) Å] and the cyclohexene ring (C14–C19) is puckered with the puckering parameters (Cremer & Pople, 1975) of Q_T = 0.452 (3) Å, θ = 57.0 (4) ° and ϕ = 131.7 (4) °. The cyclohexene ring (C1–C6) attached to the xanthene system adopts an envelope conformation with the puckering parameters of Q_T = 0.477 (3) Å, θ = 60.5 (2) ° and ϕ = 178.1 (3) °. The bond lengths and bond angles fall within a normal range and are comparable with those of the similar structures previously reported (Mohamed et al., 2012b; Kurbanova et al., 2012; Abdelhamid et al., 2011; Mohamed et al., 2011; Reddy et al., 2009).

Intermolecular O2—H···O1ⁱ and C5—H5A···O1ⁱ [(i): x - 0.5, -y + 1.5, z; Table 1] hydrogen bonds form infinite chains of R²₁(6)ring motifs (Bernstein et al., 1995; Fig. 2) along the a axis with xanthen groups in alternating zigzag manner.

Related literature top

For the bioactivity of xanthene compounds, see: Mohamed et al. (2012a); Mo et al. (2010) and for their fluorescence properties, see: Menchen et al. (2003). For similar structures see: Mohamed et al. (2011, 2012b); Kurbanova et al. (2012); Abdelhamid et al. (2011); Reddy et al. (2009). For ring conformations, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was obtained as a major product from a three component reaction of 112 mg (1 mmol) cyclohexane-1,3-dione, 112 mg(1 mmol)salicylaldehyde and 137 mg (1 mmol) 1-(3-aminophenyl)ethanol in 50 ml ethanol [the amino alcohol in this reaction has not been reacted instead acted as a Lewis base catalyst]. The reaction mixture was refluxed for 3 h at 350 K, then cooled at room temperature in fume cupboard where the excess solvent was evaporated. The solid that formed was filtered off, washed with cold ethanol and dried under vacuum. On crystallization from ethanol shiny crystals (m.p. 503 K) were collected in an excellent yield (92%). Crystals suitable for X-ray diffraction were grown by slow evaporation method over two days using ethanol solution.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The intermolecular hydrogen bonds in (I) indicated as dashed lines along [001]. H-atoms not involved in hydrogen bonding are omitted.

9-(2-Hydroxy-6-oxocyclohex-1-en-1-yl)-2,3,4,9-tetrahydro-1H-xanthen-1-one top

Crystal data top

C₁₉H₁₈O₄	F(000) = 656
M_r = 310.33	D_x = 1.346 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3393 reflections
a = 13.4420 (18) Å	θ = 2.9–27.9°
b = 8.0015 (10) Å	µ = 0.09 mm⁻¹
c = 14.2416 (18) Å	T = 130 K
V = 1531.8 (3) Å³	Prism, pale-yellow
Z = 4	0.37 × 0.24 × 0.15 mm

Data collection top

Bruker SMART APEX diffractometer	1901 independent reflections
Radiation source: sealed tube	1799 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 27.9°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −17→17
T_min = 0.966, T_max = 0.986	k = −10→10
13880 measured reflections	l = −18→18

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)] = 0.043	Hydrogen site location: difference Fourier map
wR(F²) = 0.111	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0739P)² + 0.3774P] where P = (F_o² + 2F_c²)/3
1901 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.39 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₉H₁₈O₄	V = 1531.8 (3) Å³
M_r = 310.33	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 13.4420 (18) Å	µ = 0.09 mm⁻¹
b = 8.0015 (10) Å	T = 130 K
c = 14.2416 (18) Å	0.37 × 0.24 × 0.15 mm

Data collection top

Bruker SMART APEX diffractometer	1901 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1799 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.986	R_int = 0.032
13880 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	1 restraint
wR(F²) = 0.111	H-atom parameters constrained
S = 1.06	Δρ_max = 0.39 e Å⁻³
1901 reflections	Δρ_min = −0.18 e Å⁻³
209 parameters

Special details top

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	0.28192 (10)	0.69820 (18)	0.43470 (13)	0.0184 (4)
O2	−0.06046 (11)	0.61746 (18)	0.43776 (14)	0.0212 (4)
O3	0.32497 (11)	0.31450 (18)	0.43000 (13)	0.0201 (4)
O4	0.06177 (15)	0.4417 (3)	0.63635 (14)	0.0332 (6)
C1	0.11167 (14)	0.6473 (2)	0.44797 (16)	0.0146 (5)
C2	0.19662 (15)	0.7556 (2)	0.44266 (16)	0.0148 (5)
C3	0.18243 (15)	0.9436 (2)	0.4447 (2)	0.0213 (6)
C4	0.08584 (18)	0.9945 (3)	0.4923 (2)	0.0287 (7)
C5	−0.00064 (16)	0.9004 (3)	0.4487 (2)	0.0282 (7)
C6	0.01837 (15)	0.7154 (2)	0.44477 (17)	0.0170 (5)
C7	0.12663 (14)	0.4583 (2)	0.44760 (16)	0.0143 (5)
C8	0.16996 (17)	0.3960 (3)	0.35574 (16)	0.0169 (6)
C9	0.1140 (2)	0.4019 (3)	0.27230 (18)	0.0245 (7)
C10	0.1531 (2)	0.3453 (3)	0.18896 (19)	0.0309 (8)
C11	0.2489 (3)	0.2819 (3)	0.18615 (19)	0.0337 (8)
C12	0.3059 (2)	0.2744 (3)	0.26740 (19)	0.0273 (7)
C13	0.26539 (18)	0.3314 (3)	0.35123 (17)	0.0189 (6)
C14	0.28205 (18)	0.3342 (3)	0.51564 (16)	0.0175 (6)
C15	0.35058 (18)	0.2726 (3)	0.59122 (19)	0.0247 (7)
C16	0.3183 (2)	0.3350 (3)	0.6870 (2)	0.0312 (8)
C17	0.2073 (2)	0.3126 (4)	0.70056 (19)	0.0329 (9)
C18	0.14584 (19)	0.3913 (3)	0.62272 (17)	0.0226 (6)
C19	0.18972 (17)	0.3968 (3)	0.52852 (15)	0.0159 (6)
H2	−0.11220	0.67370	0.44770	0.0320*
H3A	0.18270	0.98680	0.37960	0.0260*
H3B	0.23900	0.99530	0.47850	0.0260*
H4A	0.08960	0.96920	0.56020	0.0340*
H4B	0.07550	1.11630	0.48490	0.0340*
H5A	−0.06160	0.92160	0.48590	0.0340*
H5B	−0.01220	0.94270	0.38430	0.0340*
H7A	0.05940	0.40600	0.45460	0.0170*
H9A	0.04840	0.44570	0.27360	0.0290*
H10A	0.11430	0.34970	0.13320	0.0370*
H11A	0.27580	0.24340	0.12840	0.0400*
H12A	0.37160	0.23090	0.26570	0.0330*
H15A	0.41910	0.31150	0.57810	0.0300*
H15B	0.35100	0.14880	0.59120	0.0300*
H16A	0.35440	0.27270	0.73640	0.0370*
H16B	0.33550	0.45480	0.69320	0.0370*
H17A	0.18780	0.36300	0.76130	0.0390*
H17B	0.19210	0.19170	0.70360	0.0390*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0111 (6)	0.0182 (6)	0.0260 (8)	−0.0017 (5)	0.0003 (7)	0.0003 (7)
O2	0.0101 (7)	0.0176 (7)	0.0358 (9)	0.0000 (5)	−0.0006 (8)	−0.0019 (8)
O3	0.0144 (7)	0.0194 (7)	0.0265 (9)	0.0032 (5)	0.0007 (7)	0.0003 (7)
O4	0.0272 (10)	0.0447 (11)	0.0278 (10)	0.0020 (8)	0.0065 (8)	−0.0008 (8)
C1	0.0129 (9)	0.0127 (8)	0.0181 (10)	−0.0003 (7)	−0.0004 (8)	−0.0004 (8)
C2	0.0138 (9)	0.0145 (8)	0.0160 (9)	−0.0005 (7)	−0.0019 (8)	0.0003 (9)
C3	0.0165 (9)	0.0131 (8)	0.0343 (12)	−0.0026 (7)	0.0002 (10)	0.0005 (10)
C4	0.0197 (11)	0.0170 (10)	0.0493 (16)	−0.0001 (9)	0.0003 (11)	−0.0086 (11)
C5	0.0158 (10)	0.0142 (9)	0.0547 (17)	0.0031 (7)	−0.0026 (12)	−0.0034 (12)
C6	0.0153 (9)	0.0142 (8)	0.0214 (10)	0.0000 (7)	−0.0018 (9)	−0.0018 (9)
C7	0.0119 (8)	0.0119 (7)	0.0192 (10)	−0.0011 (7)	−0.0014 (8)	0.0009 (8)
C8	0.0220 (11)	0.0110 (10)	0.0177 (10)	−0.0013 (8)	−0.0006 (9)	−0.0005 (8)
C9	0.0336 (13)	0.0180 (11)	0.0218 (11)	−0.0016 (10)	−0.0075 (10)	0.0001 (9)
C10	0.0510 (17)	0.0207 (11)	0.0210 (12)	−0.0021 (11)	−0.0086 (12)	−0.0012 (10)
C11	0.0585 (19)	0.0233 (12)	0.0192 (12)	0.0008 (12)	0.0094 (12)	−0.0019 (10)
C12	0.0342 (14)	0.0179 (11)	0.0297 (13)	0.0035 (10)	0.0118 (11)	0.0002 (10)
C13	0.0235 (11)	0.0133 (10)	0.0198 (10)	−0.0012 (8)	0.0033 (9)	0.0005 (8)
C14	0.0198 (10)	0.0121 (9)	0.0207 (11)	−0.0017 (8)	−0.0039 (9)	0.0018 (8)
C15	0.0230 (12)	0.0209 (11)	0.0303 (13)	0.0016 (9)	−0.0069 (10)	0.0052 (10)
C16	0.0371 (15)	0.0303 (13)	0.0262 (13)	0.0039 (11)	−0.0113 (11)	0.0021 (11)
C17	0.0446 (17)	0.0358 (15)	0.0184 (12)	−0.0025 (12)	−0.0003 (11)	0.0070 (11)
C18	0.0266 (12)	0.0210 (10)	0.0201 (11)	−0.0048 (9)	0.0027 (10)	−0.0017 (9)
C19	0.0198 (10)	0.0119 (9)	0.0159 (10)	−0.0019 (8)	−0.0016 (8)	0.0013 (8)

Geometric parameters (Å, º) top

O1—C2	1.240 (2)	C14—C15	1.500 (3)
O2—C6	1.322 (2)	C15—C16	1.516 (4)
O3—C13	1.385 (3)	C16—C17	1.515 (4)
O3—C14	1.358 (3)	C17—C18	1.519 (4)
O4—C18	1.216 (3)	C18—C19	1.466 (3)
O2—H2	0.8400	C3—H3A	0.9900
C1—C6	1.368 (3)	C3—H3B	0.9900
C1—C7	1.526 (2)	C4—H4A	0.9900
C1—C2	1.436 (3)	C4—H4B	0.9900
C2—C3	1.517 (2)	C5—H5A	0.9900
C3—C4	1.520 (3)	C5—H5B	0.9900
C4—C5	1.518 (3)	C7—H7A	1.0000
C5—C6	1.503 (3)	C9—H9A	0.9500
C7—C19	1.513 (3)	C10—H10A	0.9500
C7—C8	1.516 (3)	C11—H11A	0.9500
C8—C9	1.407 (3)	C12—H12A	0.9500
C8—C13	1.385 (3)	C15—H15A	0.9900
C9—C10	1.375 (4)	C15—H15B	0.9900
C10—C11	1.385 (5)	C16—H16A	0.9900
C11—C12	1.389 (4)	C16—H16B	0.9900
C12—C13	1.389 (4)	C17—H17A	0.9900
C14—C19	1.351 (3)	C17—H17B	0.9900

C13—O3—C14	118.06 (18)	C2—C3—H3B	109.00
C6—O2—H2	109.00	C4—C3—H3A	109.00
C2—C1—C7	119.56 (16)	C4—C3—H3B	109.00
C6—C1—C7	121.03 (16)	H3A—C3—H3B	108.00
C2—C1—C6	119.14 (15)	C3—C4—H4A	110.00
O1—C2—C3	119.03 (17)	C3—C4—H4B	110.00
C1—C2—C3	119.85 (17)	C5—C4—H4A	110.00
O1—C2—C1	121.11 (15)	C5—C4—H4B	110.00
C2—C3—C4	112.44 (17)	H4A—C4—H4B	108.00
C3—C4—C5	109.8 (2)	C4—C5—H5A	109.00
C4—C5—C6	111.93 (19)	C4—C5—H5B	109.00
O2—C6—C5	116.77 (17)	C6—C5—H5A	109.00
C1—C6—C5	123.15 (17)	C6—C5—H5B	109.00
O2—C6—C1	120.08 (15)	H5A—C5—H5B	108.00
C1—C7—C19	113.18 (17)	C1—C7—H7A	107.00
C8—C7—C19	109.57 (17)	C8—C7—H7A	107.00
C1—C7—C8	112.30 (18)	C19—C7—H7A	107.00
C7—C8—C13	121.2 (2)	C8—C9—H9A	120.00
C9—C8—C13	118.0 (2)	C10—C9—H9A	120.00
C7—C8—C9	120.8 (2)	C9—C10—H10A	120.00
C8—C9—C10	120.9 (2)	C11—C10—H10A	120.00
C9—C10—C11	120.1 (3)	C10—C11—H11A	120.00
C10—C11—C12	120.3 (3)	C12—C11—H11A	120.00
C11—C12—C13	119.0 (3)	C11—C12—H12A	121.00
O3—C13—C12	115.9 (2)	C13—C12—H12A	120.00
C8—C13—C12	121.7 (2)	C14—C15—H15A	109.00
O3—C13—C8	122.3 (2)	C14—C15—H15B	109.00
O3—C14—C15	110.2 (2)	C16—C15—H15A	109.00
O3—C14—C19	123.7 (2)	C16—C15—H15B	109.00
C15—C14—C19	126.1 (2)	H15A—C15—H15B	108.00
C14—C15—C16	111.2 (2)	C15—C16—H16A	109.00
C15—C16—C17	111.0 (2)	C15—C16—H16B	109.00
C16—C17—C18	113.2 (2)	C17—C16—H16A	109.00
O4—C18—C19	120.7 (2)	C17—C16—H16B	109.00
C17—C18—C19	117.5 (2)	H16A—C16—H16B	108.00
O4—C18—C17	121.8 (2)	C16—C17—H17A	109.00
C7—C19—C18	118.8 (2)	C16—C17—H17B	109.00
C14—C19—C18	118.9 (2)	C18—C17—H17A	109.00
C7—C19—C14	122.2 (2)	C18—C17—H17B	109.00
C2—C3—H3A	109.00	H17A—C17—H17B	108.00

C14—O3—C13—C8	11.8 (3)	C8—C7—C19—C14	15.1 (3)
C14—O3—C13—C12	−166.1 (2)	C8—C7—C19—C18	−159.4 (2)
C13—O3—C14—C15	166.70 (19)	C7—C8—C9—C10	−179.9 (2)
C13—O3—C14—C19	−11.8 (3)	C13—C8—C9—C10	−0.1 (4)
C6—C1—C2—O1	−171.8 (2)	C7—C8—C13—O3	2.3 (3)
C6—C1—C2—C3	6.9 (3)	C7—C8—C13—C12	−179.8 (2)
C7—C1—C2—O1	2.4 (3)	C9—C8—C13—O3	−177.5 (2)
C7—C1—C2—C3	−178.9 (2)	C9—C8—C13—C12	0.3 (4)
C2—C1—C6—O2	171.6 (2)	C8—C9—C10—C11	−0.2 (4)
C2—C1—C6—C5	−8.3 (4)	C9—C10—C11—C12	0.3 (4)
C7—C1—C6—O2	−2.5 (4)	C10—C11—C12—C13	0.0 (4)
C7—C1—C6—C5	177.6 (2)	C11—C12—C13—O3	177.7 (2)
C2—C1—C7—C8	−65.0 (3)	C11—C12—C13—C8	−0.3 (4)
C2—C1—C7—C19	59.7 (3)	O3—C14—C15—C16	164.41 (19)
C6—C1—C7—C8	109.0 (2)	C19—C14—C15—C16	−17.2 (3)
C6—C1—C7—C19	−126.3 (2)	O3—C14—C19—C7	−2.7 (4)
O1—C2—C3—C4	−157.1 (2)	O3—C14—C19—C18	171.8 (2)
C1—C2—C3—C4	24.2 (3)	C15—C14—C19—C7	179.1 (2)
C2—C3—C4—C5	−52.2 (3)	C15—C14—C19—C18	−6.4 (4)
C3—C4—C5—C6	50.8 (3)	C14—C15—C16—C17	46.1 (3)
C4—C5—C6—O2	158.5 (2)	C15—C16—C17—C18	−54.0 (3)
C4—C5—C6—C1	−21.6 (3)	C16—C17—C18—O4	−151.9 (3)
C1—C7—C8—C9	−68.2 (3)	C16—C17—C18—C19	31.2 (3)
C1—C7—C8—C13	111.9 (2)	O4—C18—C19—C7	−3.0 (4)
C19—C7—C8—C9	165.1 (2)	O4—C18—C19—C14	−177.7 (2)
C19—C7—C8—C13	−14.7 (3)	C17—C18—C19—C7	173.9 (2)
C1—C7—C19—C14	−111.1 (2)	C17—C18—C19—C14	−0.8 (3)
C1—C7—C19—C18	74.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.84	1.76	2.582 (2)	164
C5—H5A···O1ⁱ	0.99	2.42	3.034 (3)	119
C7—H7A···O2	1.00	2.35	2.822 (2)	108

Symmetry code: (i) x−1/2, −y+3/2, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈O₄
M_r	310.33
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	130
a, b, c (Å)	13.4420 (18), 8.0015 (10), 14.2416 (18)
V (Å³)	1531.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.37 × 0.24 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.966, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	13880, 1901, 1799
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.111, 1.06
No. of reflections	1901
No. of parameters	209
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.18

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.8400	1.7600	2.582 (2)	164.00
C5—H5A···O1ⁱ	0.9900	2.4200	3.034 (3)	119.00

Symmetry code: (i) x−1/2, −y+3/2, z.

Acknowledgements

Manchester Metropolitan University, Universität Paderborn, Erciyes University and Quaid-I-Azam University are gratefully acknowledged for supporting this study.

References

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