Ethyl 6-(4-ethoxy­phen­yl)-4-(furan-2-yl)-2-oxocyclo­hex-3-ene-1-carboxyl­ate

Badshah, A.; Hasan, A.; Barbarín, C.R.; Abbas, A.; Ali, S.

doi:10.1107/S1600536808040130

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o70

doi:10.1107/S1600536808040130

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Ethyl 6-(4-ethoxyphenyl)-4-(furan-2-yl)-2-oxocyclohex-3-ene-1-carboxylate

Amir Badshah,^a Aurangzeb Hasan,^a ^* Cecilia R. Barbarín,^b Asghar Abbas ^a and Sajid Ali ^a

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDivisión de Estudios de Posgrado, Facultad de Ciencias Químicas, UANL, Guerreo y Progreso S/N, Col. Treviño, CP, 64570, Monterrey, NL, Mexico
^*Correspondence e-mail: flavonoids@hotmail.com

(Received 5 September 2008; accepted 28 November 2008; online 10 December 2008)

The title compound, C₂₁H₂₂O₅, was prepared by NaOH-catalysed cyclocondensation of 3-(4-ethoxyphenyl)-1-(furan-2-yl)prop-2-en-1-one with ethyl acetoacetate. In the crystal, C—H⋯O and C—H⋯π interactions link the molecules. In the title molecule, the furan and cyclohexene rings are almost parallel [6.77 (11)°] and the cyclohexene ring is approximately perpendicular to the benzene ring [84.79 (5)°].

Related literature

For background to cyclohexenones, see: Eddington et al. (2000 ); Li & Strobel (2001 ); Luu et al. (2000 ); Padmavathi et al. (2000 , 2001 ).

Experimental

Crystal data

C₂₁H₂₂O₅
M_r = 354.39
Monoclinic, P 2₁ /n
a = 7.361 (3) Å
b = 17.350 (4) Å
c = 14.473 (3) Å
β = 104.07 (2)°
V = 1792.8 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.60 × 0.40 × 0.40 mm

Data collection

Bruker P4 diffractometer
Absorption correction: none
8745 measured reflections
5218 independent reflections
3806 reflections with I > 2σ(I)
R_int = 0.021
3 standard reflections every 97 reflections intensity decay: 3.4%

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.135
S = 1.06
5218 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O3ⁱ	0.93	2.55	3.441 (2)	160
C19—H19A⋯Cgⁱⁱ	0.93	2.82	3.641 (2)	147
C21—H21A⋯Cgⁱⁱⁱ	0.96	2.94	3.546 (3)	122
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg is the centroid of the furanyl ring O1/C1–C4.

Data collection: XSCANS (Siemens, 1999 ); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL-Plus.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808040130/fb2116sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808040130/fb2116Isup2.hkl

checkCIF report

Comment top

Cyclohexenones are prepared either from natural sources or entirely via synthetic routes. The motive for their preparation is a variety of medical effects. The molecules have anticonvulsant, antimalarial, anti-inflammatory and cardiovascular effects (Eddington et al., 2000). Cyclohexenones are also important intermediates for many biologically active compounds (Padmavathi et al., 2000, 2001). A series of novel compounds has been synthesized, known as cyclohexenoic long chain fatty alcohols, which are used in the treatment of neurological disorders (Luu et al., 2000). A number of their derivatives have fungicidal and antitumor activities (Li et al., 2001).

The title compound (Fig. 1) is a derivative of 1-(furan-2-yl)-3-(4-ethoxyphenyl)prop-2-en-1-one.

Two rings of the title molecule, i.e. furan-2-yl [O1\C1 ··· C4] and the cyclohexene [C5 ··· C10], are almost parallel containing 6.77 (11)°. Cyclohexene is approximately perpendicular to the benzene ring [C14 ··· C19], containing 84.79 (05)°. The title molecule has two asymmetric carbon atoms C8 and C9. The respective configurations are SR and RS within the racemic pair in the structure.

There are weak intermolecular interactions only in the structure that are indicated by geometry, X-H···O and C—H···π-electron ring contacts (Tab. 1). The molecular packing is shown in Fig. 2.

Related literature top

For background to cyclohexenones, see: Eddington et al. (2000); Li & Strobel (2001); Luu et al. (2000); Padmavathi et al. (2000, 2001).

Experimental top

The title compound was synthesized by refluxing ethyl acetoacetate (0.39 g, 0.40 ml, 3 mmol) with 1-(furan-2-yl)-3-(4-ethoxyphenyl)prop-2-en-1-one (3 mmol, 0.726 g) for 2 h in 10–15 ml of ethanol in presence of 0.5 ml 10% NaOH as shown in Fig. 3. The reaction mixture was then poured while having been stirred intensively into 200 ml of ice-cold water. The mixture was kept at room temperature until the reaction product separated as a solid, which was filtered off and recrystallized from ethanol. The grown crystals were prismatic, yellow and with approximate dimensions of 0.4×0.4×0.6 mm. Yield: 70%, m.p.: 388 K.

Computing details top

Data collection: XSCANS (Siemens, 1999); cell refinement: XSCANS (Siemens, 1999); data reduction: XSCANS (Siemens, 1999); program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 2008); program(s) used to refine structure: SHELXTL-Plus (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL-Plus (Sheldrick, 2008).

Figures top

	Fig. 1. The title molecule showing the atom-labelling scheme. The displacement ellipsoids are drawn at the 40% probability level and the H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The packing diagram of the title compound, viewed along the the a-axis showing the weak hydrogen-bond and C—H···π electron interactions.
	Fig. 3. Preparation of the title compound.

(1SR,6RS)-Ethyl 6-(4-ethoxyphenyl)-4-(furan-2-yl)-2-oxocyclohex-3-ene-1-carboxylate top

Crystal data top

C₂₁H₂₂O₅	F(000) = 752
M_r = 354.39	D_x = 1.313 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 388 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.361 (3) Å	Cell parameters from 86 reflections
b = 17.350 (4) Å	θ = 4.6–12.9°
c = 14.473 (3) Å	µ = 0.09 mm⁻¹
β = 104.07 (2)°	T = 298 K
V = 1792.8 (9) Å³	Prism, yellow
Z = 4	0.60 × 0.40 × 0.40 mm

Data collection top

Bruker P4 diffractometer	R_int = 0.021
Radiation source: fine-focus sealed tube	θ_max = 30.0°, θ_min = 2.4°
Graphite monochromator	h = −10→4
ω scans	k = −24→1
8745 measured reflections	l = −20→20
5218 independent reflections	3 standard reflections every 97 reflections
3806 reflections with I > 2σ(I)	intensity decay: 3.4%

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)] = 0.047	Hydrogen site location: difference Fourier map
wR(F²) = 0.135	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.057P)² + 0.3325P] where P = (F_o² + 2F_c²)/3
5218 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³
86 constraints

Crystal data top

C₂₁H₂₂O₅	V = 1792.8 (9) Å³
M_r = 354.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.361 (3) Å	µ = 0.09 mm⁻¹
b = 17.350 (4) Å	T = 298 K
c = 14.473 (3) Å	0.60 × 0.40 × 0.40 mm
β = 104.07 (2)°

Data collection top

Bruker P4 diffractometer	R_int = 0.021
8745 measured reflections	3 standard reflections every 97 reflections
5218 independent reflections	intensity decay: 3.4%
3806 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.06	Δρ_max = 0.27 e Å⁻³
5218 reflections	Δρ_min = −0.17 e Å⁻³
237 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
O1	−0.07980 (14)	0.45302 (6)	0.31575 (9)	0.0611 (3)
O2	0.43726 (17)	0.45205 (7)	0.60674 (8)	0.0646 (3)
O3	0.67391 (17)	0.29800 (7)	0.65190 (8)	0.0627 (3)
O4	0.86811 (14)	0.37514 (6)	0.59822 (8)	0.0571 (3)
O5	1.03226 (14)	0.08582 (5)	0.40318 (7)	0.0495 (2)
C1	−0.2189 (2)	0.45660 (10)	0.23520 (15)	0.0697 (5)
H1A	−0.3227	0.4888	0.2267	0.084*
C2	−0.1874 (2)	0.40812 (10)	0.16994 (13)	0.0642 (4)
H2A	−0.2628	0.4004	0.1090	0.077*
C3	−0.0168 (2)	0.37048 (9)	0.21122 (11)	0.0514 (3)
H3A	0.0416	0.3328	0.1829	0.062*
C4	0.04471 (17)	0.39962 (7)	0.29930 (10)	0.0439 (3)
C5	0.21001 (17)	0.38693 (7)	0.37425 (10)	0.0411 (3)
C6	0.23954 (19)	0.42500 (8)	0.45737 (11)	0.0488 (3)
H6A	0.1459	0.4574	0.4679	0.059*
C7	0.4111 (2)	0.41770 (8)	0.53120 (10)	0.0471 (3)
C8	0.56299 (18)	0.36875 (7)	0.50669 (9)	0.0422 (3)
H8A	0.6283	0.4004	0.4688	0.051*
C9	0.47735 (17)	0.29939 (7)	0.44584 (9)	0.0394 (3)
H9A	0.3986	0.2718	0.4806	0.047*
C10	0.34964 (17)	0.33007 (8)	0.35447 (9)	0.0415 (3)
H10A	0.4249	0.3548	0.3165	0.050*
H10B	0.2835	0.2874	0.3179	0.050*
C11	0.7048 (2)	0.34303 (8)	0.59512 (9)	0.0457 (3)
C12	1.0290 (2)	0.34644 (11)	0.66794 (13)	0.0672 (5)
H12A	0.9931	0.3332	0.7262	0.081*
H12B	1.1248	0.3860	0.6827	0.081*
C13	1.1037 (3)	0.27755 (12)	0.62977 (14)	0.0757 (5)
H13A	1.2236	0.2645	0.6702	0.114*
H13B	1.1170	0.2882	0.5667	0.114*
H13C	1.0189	0.2352	0.6277	0.114*
C14	0.62510 (16)	0.24380 (7)	0.43058 (8)	0.0373 (2)
C15	0.6367 (2)	0.17049 (8)	0.46933 (10)	0.0454 (3)
H15A	0.5501	0.1555	0.5031	0.054*
C16	0.7726 (2)	0.11937 (8)	0.45920 (10)	0.0482 (3)
H16A	0.7773	0.0705	0.4861	0.058*
C17	0.90234 (17)	0.14023 (7)	0.40922 (9)	0.0381 (3)
C18	0.89386 (18)	0.21308 (7)	0.36978 (10)	0.0420 (3)
H18A	0.9803	0.2279	0.3358	0.050*
C19	0.75621 (18)	0.26366 (7)	0.38113 (10)	0.0431 (3)
H19A	0.7518	0.3126	0.3546	0.052*
C20	1.1525 (2)	0.10138 (8)	0.34250 (11)	0.0516 (3)
H20A	1.2328	0.1449	0.3665	0.062*
H20B	1.0795	0.1137	0.2789	0.062*
C21	1.2679 (3)	0.03130 (10)	0.33988 (16)	0.0721 (5)
H21A	1.3438	0.0389	0.2953	0.108*
H21B	1.1871	−0.0122	0.3206	0.108*
H21C	1.3471	0.0220	0.4021	0.108*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0433 (5)	0.0450 (5)	0.0870 (8)	0.0109 (4)	0.0004 (5)	−0.0034 (5)
O2	0.0676 (7)	0.0628 (7)	0.0603 (6)	0.0169 (5)	0.0094 (5)	−0.0202 (5)
O3	0.0758 (8)	0.0597 (7)	0.0523 (6)	0.0065 (6)	0.0152 (5)	0.0072 (5)
O4	0.0461 (6)	0.0526 (6)	0.0649 (6)	0.0054 (4)	−0.0016 (5)	0.0015 (5)
O5	0.0533 (6)	0.0412 (5)	0.0612 (6)	0.0136 (4)	0.0276 (5)	0.0092 (4)
C1	0.0432 (8)	0.0489 (8)	0.1032 (14)	0.0069 (6)	−0.0088 (8)	0.0089 (9)
C2	0.0507 (8)	0.0561 (9)	0.0740 (10)	−0.0053 (7)	−0.0081 (7)	0.0176 (8)
C3	0.0451 (7)	0.0488 (7)	0.0575 (8)	−0.0019 (6)	0.0068 (6)	0.0090 (6)
C4	0.0351 (6)	0.0335 (6)	0.0620 (8)	0.0017 (5)	0.0095 (5)	0.0077 (5)
C5	0.0351 (6)	0.0344 (6)	0.0540 (7)	0.0007 (5)	0.0110 (5)	0.0047 (5)
C6	0.0429 (7)	0.0422 (7)	0.0612 (8)	0.0107 (6)	0.0123 (6)	−0.0033 (6)
C7	0.0482 (7)	0.0392 (6)	0.0532 (7)	0.0068 (5)	0.0109 (6)	−0.0051 (6)
C8	0.0409 (6)	0.0375 (6)	0.0467 (6)	0.0037 (5)	0.0078 (5)	−0.0007 (5)
C9	0.0384 (6)	0.0371 (6)	0.0435 (6)	0.0038 (5)	0.0119 (5)	−0.0010 (5)
C10	0.0360 (6)	0.0418 (6)	0.0458 (6)	0.0034 (5)	0.0083 (5)	−0.0012 (5)
C11	0.0514 (7)	0.0393 (6)	0.0442 (7)	0.0092 (6)	0.0076 (5)	−0.0061 (5)
C12	0.0538 (9)	0.0695 (10)	0.0660 (10)	0.0137 (8)	−0.0094 (7)	−0.0107 (8)
C13	0.0679 (11)	0.0849 (13)	0.0670 (10)	0.0279 (10)	0.0021 (8)	−0.0060 (9)
C14	0.0368 (6)	0.0366 (6)	0.0381 (6)	0.0038 (5)	0.0081 (5)	−0.0020 (5)
C15	0.0512 (7)	0.0416 (7)	0.0499 (7)	0.0034 (5)	0.0251 (6)	0.0051 (5)
C16	0.0597 (8)	0.0352 (6)	0.0572 (8)	0.0075 (6)	0.0286 (6)	0.0095 (6)
C17	0.0392 (6)	0.0354 (6)	0.0405 (6)	0.0052 (5)	0.0111 (5)	0.0006 (5)
C18	0.0389 (6)	0.0400 (6)	0.0502 (7)	0.0018 (5)	0.0169 (5)	0.0074 (5)
C19	0.0424 (7)	0.0354 (6)	0.0529 (7)	0.0041 (5)	0.0144 (5)	0.0083 (5)
C20	0.0475 (7)	0.0490 (7)	0.0645 (9)	0.0072 (6)	0.0260 (7)	0.0040 (6)
C21	0.0684 (11)	0.0543 (9)	0.1091 (15)	0.0148 (8)	0.0516 (11)	0.0028 (9)

Geometric parameters (Å, º) top

O1—C1	1.353 (2)	C9—H9A	0.9800
O1—C4	1.3642 (16)	C10—H10A	0.9700
O2—C7	1.2186 (17)	C10—H10B	0.9700
O3—C11	1.1949 (18)	C12—C13	1.478 (2)
O4—C11	1.3157 (18)	C12—H12A	0.9700
O4—C12	1.4449 (18)	C12—H12B	0.9700
O5—C17	1.3616 (15)	C13—H13A	0.9600
O5—C20	1.4164 (17)	C13—H13B	0.9600
C1—C2	1.327 (3)	C13—H13C	0.9600
C1—H1A	0.9300	C14—C19	1.3776 (18)
C2—C3	1.413 (2)	C14—C15	1.3842 (18)
C2—H2A	0.9300	C15—C16	1.3710 (19)
C3—C4	1.344 (2)	C15—H15A	0.9300
C3—H3A	0.9300	C16—C17	1.3791 (18)
C4—C5	1.4367 (19)	C16—H16A	0.9300
C5—C6	1.343 (2)	C17—C18	1.3820 (17)
C5—C10	1.5015 (18)	C18—C19	1.3801 (18)
C6—C7	1.448 (2)	C18—H18A	0.9300
C6—H6A	0.9300	C19—H19A	0.9300
C7—C8	1.5133 (19)	C20—C21	1.489 (2)
C8—C11	1.5090 (19)	C20—H20A	0.9700
C8—C9	1.5334 (18)	C20—H20B	0.9700
C8—H8A	0.9800	C21—H21A	0.9600
C9—C14	1.5095 (17)	C21—H21B	0.9600
C9—C10	1.5204 (18)	C21—H21C	0.9600

C1—O1—C4	106.29 (13)	O4—C11—C8	109.97 (12)
C11—O4—C12	117.70 (13)	O4—C12—C13	109.51 (13)
C17—O5—C20	117.53 (10)	O4—C12—H12A	109.8
C2—C1—O1	110.96 (14)	C13—C12—H12A	109.8
C2—C1—H1A	124.5	O4—C12—H12B	109.8
O1—C1—H1A	124.5	C13—C12—H12B	109.8
C1—C2—C3	106.45 (15)	H12A—C12—H12B	108.2
C1—C2—H2A	126.8	C12—C13—H13A	109.5
C3—C2—H2A	126.8	C12—C13—H13B	109.5
C4—C3—C2	106.68 (15)	H13A—C13—H13B	109.5
C4—C3—H3A	126.7	C12—C13—H13C	109.5
C2—C3—H3A	126.7	H13A—C13—H13C	109.5
C3—C4—O1	109.60 (12)	H13B—C13—H13C	109.5
C3—C4—C5	133.38 (13)	C19—C14—C15	117.27 (11)
O1—C4—C5	117.00 (13)	C19—C14—C9	122.46 (11)
C6—C5—C4	121.59 (12)	C15—C14—C9	120.24 (11)
C6—C5—C10	121.65 (12)	C16—C15—C14	121.73 (12)
C4—C5—C10	116.75 (12)	C16—C15—H15A	119.1
C5—C6—C7	122.71 (12)	C14—C15—H15A	119.1
C5—C6—H6A	118.6	C15—C16—C17	120.16 (12)
C7—C6—H6A	118.6	C15—C16—H16A	119.9
O2—C7—C6	122.59 (13)	C17—C16—H16A	119.9
O2—C7—C8	121.33 (13)	O5—C17—C16	116.00 (11)
C6—C7—C8	115.95 (12)	O5—C17—C18	124.71 (11)
C11—C8—C7	111.43 (11)	C16—C17—C18	119.28 (11)
C11—C8—C9	110.98 (11)	C19—C18—C17	119.55 (12)
C7—C8—C9	110.55 (11)	C19—C18—H18A	120.2
C11—C8—H8A	107.9	C17—C18—H18A	120.2
C7—C8—H8A	107.9	C14—C19—C18	122.01 (12)
C9—C8—H8A	107.9	C14—C19—H19A	119.0
C14—C9—C10	114.30 (10)	C18—C19—H19A	119.0
C14—C9—C8	112.04 (10)	O5—C20—C21	107.84 (12)
C10—C9—C8	107.80 (10)	O5—C20—H20A	110.1
C14—C9—H9A	107.5	C21—C20—H20A	110.1
C10—C9—H9A	107.5	O5—C20—H20B	110.1
C8—C9—H9A	107.5	C21—C20—H20B	110.1
C5—C10—C9	111.80 (11)	H20A—C20—H20B	108.5
C5—C10—H10A	109.3	C20—C21—H21A	109.5
C9—C10—H10A	109.3	C20—C21—H21B	109.5
C5—C10—H10B	109.3	H21A—C21—H21B	109.5
C9—C10—H10B	109.3	C20—C21—H21C	109.5
H10A—C10—H10B	107.9	H21A—C21—H21C	109.5
O3—C11—O4	125.33 (13)	H21B—C21—H21C	109.5
O3—C11—C8	124.65 (14)

C4—O1—C1—C2	0.19 (19)	C8—C9—C10—C5	−52.86 (14)
O1—C1—C2—C3	0.2 (2)	C12—O4—C11—O3	8.9 (2)
C1—C2—C3—C4	−0.55 (18)	C12—O4—C11—C8	−168.69 (12)
C2—C3—C4—O1	0.68 (16)	C7—C8—C11—O3	68.81 (17)
C2—C3—C4—C5	−177.72 (14)	C9—C8—C11—O3	−54.86 (17)
C1—O1—C4—C3	−0.55 (16)	C7—C8—C11—O4	−113.62 (13)
C1—O1—C4—C5	178.14 (13)	C9—C8—C11—O4	122.71 (12)
C3—C4—C5—C6	179.29 (15)	C11—O4—C12—C13	83.8 (2)
O1—C4—C5—C6	0.99 (19)	C10—C9—C14—C19	58.90 (16)
C3—C4—C5—C10	0.3 (2)	C8—C9—C14—C19	−64.11 (16)
O1—C4—C5—C10	−177.97 (11)	C10—C9—C14—C15	−123.20 (13)
C4—C5—C6—C7	−175.17 (13)	C8—C9—C14—C15	113.80 (14)
C10—C5—C6—C7	3.7 (2)	C19—C14—C15—C16	0.0 (2)
C5—C6—C7—O2	−179.68 (15)	C9—C14—C15—C16	−178.05 (13)
C5—C6—C7—C8	4.3 (2)	C14—C15—C16—C17	−0.1 (2)
O2—C7—C8—C11	23.0 (2)	C20—O5—C17—C16	172.14 (13)
C6—C7—C8—C11	−160.97 (12)	C20—O5—C17—C18	−8.22 (19)
O2—C7—C8—C9	146.87 (14)	C15—C16—C17—O5	179.78 (13)
C6—C7—C8—C9	−37.06 (17)	C15—C16—C17—C18	0.1 (2)
C11—C8—C9—C14	−48.49 (15)	O5—C17—C18—C19	−179.55 (13)
C7—C8—C9—C14	−172.65 (11)	C16—C17—C18—C19	0.1 (2)
C11—C8—C9—C10	−175.09 (11)	C15—C14—C19—C18	0.2 (2)
C7—C8—C9—C10	60.74 (14)	C9—C14—C19—C18	178.21 (12)
C6—C5—C10—C9	21.98 (18)	C17—C18—C19—C14	−0.3 (2)
C4—C5—C10—C9	−159.07 (11)	C17—O5—C20—C21	−174.37 (14)
C14—C9—C10—C5	−178.13 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O3ⁱ	0.93	2.55	3.441 (2)	160
C6—H6A···O1	0.93	2.42	2.761 (2)	102
C19—H19A···Cgⁱⁱ	0.93	2.82	3.641 (2)	147
C21—H21A···Cgⁱⁱⁱ	0.96	2.94	3.546 (3)	122

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x+1, y, z; (iii) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₂O₅
M_r	354.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.361 (3), 17.350 (4), 14.473 (3)
β (°)	104.07 (2)
V (Å³)	1792.8 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.60 × 0.40 × 0.40

Data collection
Diffractometer	Bruker P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8745, 5218, 3806
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.135, 1.06
No. of reflections	5218
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.17

Computer programs: XSCANS (Siemens, 1999), SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O3ⁱ	0.93	2.55	3.441 (2)	160
C6—H6A···O1	0.93	2.42	2.761 (2)	102
C19—H19A···Cgⁱⁱ	0.93	2.82	3.641 (2)	147
C21—H21A···Cgⁱⁱⁱ	0.96	2.94	3.546 (3)	122

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x+1, y, z; (iii) −x+3/2, y−1/2, −z+1/2.

Acknowledgements

AB is grateful to the Higher Education Commission of Pakistan for the grant of PhD scholarship.

References

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