Crystal structure of 7-[(2E)-2-benzyl­idene-3-oxobut­oxy]-4-methyl-2H-chromen-2-one

Caracelli, I.; Zukerman-Schpector, J.; Moran, P.J.S.; Paula, B.R.S. de; Tiekink, E.R.T.

doi:10.1107/S2056989015003084

organic compounds

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ISSN: 2056-9890

Volume 71| Part 4| April 2015| Pages o222-o223

doi:10.1107/S2056989015003084

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Crystal structure of 7-[(2E)-2-benzylidene-3-oxobutoxy]-4-methyl-2H-chromen-2-one

Ignez Caracelli,^a ^* Julio Zukerman-Schpector,^b Paulo J. S. Moran,^c Bruno R. S. de Paula ^c and Edward R. T. Tiekink ^d

^aDepartmento de Física, Universidade Federal de São Carlos, 13565-905 São Carlos, SP , Brazil, ^bDepartmento de Química, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, ^cInstituto de Química, Universidade Estadual de Campinas, C.P. 6154, 13083-970 Campinas, SP, Brazil, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: ignez@ufscar.br

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 10 February 2015; accepted 13 February 2015; online 4 March 2015)

Two independent molecules (A and B) comprise the asymmetric unit of the title compound, C₂₁H₁₈O₄. There are significant conformational differences between the molecules relating in particular to the relative orientation of the 3-oxo-2-(phenylmethylidene)butoxy substituent with respect to the superimposable chromen-2-one residues. To a first approximation, the substituents are mirror images; both are approximately perpendicular to the chromen-2-one fused ring system with dihedral angles of 88.50 (7) (A) and 81.96 (7)° (B). Another difference between the independent molecules is noted in the dihedral angles between the adjacent phenyl and but-3-en-2-one groups of 8.72 (12) (A) and 27.70 (10)° (B). The conformation about the ethene bond in both molecules is E. The crystal packing features C—H⋯O, C—H⋯π(aryl) and π–π [Cg⋯Cg = 3.6657 (8) and 3.7778 (8) Å] stacking interactions, which generate a three-dimensional network.

Keywords: crystal structure; chromen-2-one; conformation.

CCDC reference: 1049265

1. Related literature

For background to the biotransformation procedure mediated by Saccharomyces cerevisiae, see: de Paula et al. (2013 ). For the structure of the closely related compounds 7-allyloxy-2H-chromen-2-one and (3E)-3-(4-nitrophenoxymethyl)-4-phenylbut-3-en-2-one, see: Seth et al. (2011 ); Zukerman-Schpector et al. (2014 ).

2. Experimental

2.1. Crystal data

C₂₁H₁₈O₄
M_r = 334.36
Triclinic, $[P \overline 1]$
a = 9.7755 (8) Å
b = 12.3986 (10) Å
c = 14.1827 (11) Å
α = 86.293 (3)°
β = 84.328 (2)°
γ = 86.816 (2)°
V = 1704.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.52 × 0.38 × 0.33 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.664, T_max = 0.745
18494 measured reflections
6263 independent reflections
5296 reflections with I > 2σ(I)
R_int = 0.022

2.3. Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.124
S = 1.05
6263 reflections
456 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is centroid of the C6–C11 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O8ⁱ	0.93	2.59	3.4778 (19)	159
C9—H9⋯O3ⁱⁱ	0.93	2.52	3.381 (2)	155
C30—H30⋯O7ⁱⁱⁱ	0.93	2.59	3.441 (2)	153
C42—H42B⋯O1	0.96	2.53	3.427 (2)	155
C25—H25C⋯Cg1^iv	0.96	2.64	3.5238 (18)	152
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y+1, -z+1; (iii) -x+3, -y, -z+2; (iv) x+1, y-1, z.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SIR2014 (Burla et al., 2015 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ), QMOL (Gans & Shalloway, 2001 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1049265

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015003084/hb7368sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015003084/hb7368Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015003084/hb7368Isup3.cml

checkCIF report

Comment top

These title compound was synthetized to be used as a substrate in the modelling of the biotransformation procedure mediated by Saccharomyces cerevisiae,specifically in order to compare the role of different leaving groups (de Paula et al., 2013). The goal was to develop a procedure that could follow the reaction progress by colorimetric or fluorescence techniques.

Related literature top

For background to the biotransformation procedure mediated by Saccharomyces cerevisiae, see: de Paula et al. (2013). For the structure of the closely related compounds 7-allyloxy-2H-chromen-2-one and (3E)-3-(4-nitrophenoxymethyl)-4-phenylbut-3-en-2-one, see: Seth et al. (2011); Zukerman-Schpector et al. (2014).

Experimental top

4-Methylumbelliferone (352 mg, 2 mmol) and potassium carbonate (232 mg, 2.4 mmol) were added to a solution of (E)-3-bromomethyl-4-phenyl-3-buten-2-one (478 mg, 2 mmol) in dry acetone (4 ml). The solution was stirred for 3 h, and then filtered. The solvent was evaporated, and the residue was recrystallized from a CH₂Cl₂/hexane mixture to afford the product as a colourless solid in 63% yield. The product was recrystallized by slow evaporation of a 3:1 CH₂Cl₂/hexane mixture. M.pt 188.1–189.1 °C. ¹H NMR (CD₂Cl₂, 400 MHz): δ 2.40 (d, 3H, J = 1.2 Hz), 2.51 (s, 3H), 4.88 (s, 2H), 6.10 (q, 1H, J = 1.2 Hz), 6.87 (d, 1H, J = 2.4 Hz), 6.92 (dd, 1H, J = 2.4, 8.8 Hz), 7.38–7.51 (m, 5H), 7.55 (d, 1H, J = 8.8 Hz), 7.91 (s, 1H). ¹³C NMR (CD₂Cl₂, 150 MHz): δ 19.0, 26.4, 62.7, 102.5, 112.6, 113.0, 114.6, 126.3, 129.4, 130.2, 130.4, 135.0, 135.8, 146.3, 153.2, 155.8, 161.4, 162.0, 198.6.

Structure description top

For background to the biotransformation procedure mediated by Saccharomyces cerevisiae, see: de Paula et al. (2013). For the structure of the closely related compounds 7-allyloxy-2H-chromen-2-one and (3E)-3-(4-nitrophenoxymethyl)-4-phenylbut-3-en-2-one, see: Seth et al. (2011); Zukerman-Schpector et al. (2014).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SIR2014 (Burla et al., 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMOL (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structures of the two independent molecules in title compound showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level.
	Fig. 2. Superimposition of the two independent molecules. Molecule A is shown in red and inverted B in blue. The molecules have been superimposed such that the chromen-2-one rings are overlapped.
	Fig. 3. A view in projection down [0 1 1] of the unit-cell contents. The C—H···O, C—H···π and π—π interactions are shown as orange, blue and purple dashed lines, respectively.

7-[(2E)-2-Benzylidene-3-oxobutoxy]-4-methyl-2H-chromen-2-one top

Crystal data top

C₂₁H₁₈O₄	Z = 4
M_r = 334.36	F(000) = 704
Triclinic, P1	D_x = 1.303 Mg m⁻³
a = 9.7755 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.3986 (10) Å	Cell parameters from 9897 reflections
c = 14.1827 (11) Å	θ = 2.7–25.4°
α = 86.293 (3)°	µ = 0.09 mm⁻¹
β = 84.328 (2)°	T = 296 K
γ = 86.816 (2)°	Slab, colourless
V = 1704.9 (2) Å³	0.52 × 0.38 × 0.33 mm

Data collection top

Bruker APEXII CCD diffractometer	5296 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.022
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θ_max = 25.5°, θ_min = 1.5°
T_min = 0.664, T_max = 0.745	h = −11→11
18494 measured reflections	k = −14→11
6263 independent reflections	l = −17→12

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.042	w = 1/[σ²(F_o²) + (0.0611P)² + 0.3298P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.124	(Δ/σ)_max = 0.001
S = 1.05	Δρ_max = 0.34 e Å⁻³
6263 reflections	Δρ_min = −0.20 e Å⁻³
456 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0232 (15)

Crystal data top

C₂₁H₁₈O₄	γ = 86.816 (2)°
M_r = 334.36	V = 1704.9 (2) Å³
Triclinic, P1	Z = 4
a = 9.7755 (8) Å	Mo Kα radiation
b = 12.3986 (10) Å	µ = 0.09 mm⁻¹
c = 14.1827 (11) Å	T = 296 K
α = 86.293 (3)°	0.52 × 0.38 × 0.33 mm
β = 84.328 (2)°

Data collection top

Bruker APEXII CCD diffractometer	6263 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5296 reflections with I > 2σ(I)
T_min = 0.664, T_max = 0.745	R_int = 0.022
18494 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.05	Δρ_max = 0.34 e Å⁻³
6263 reflections	Δρ_min = −0.20 e Å⁻³
456 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.66167 (15)	0.54439 (11)	0.77694 (10)	0.0509 (3)
H1A	0.6424	0.5688	0.7130	0.061*
H1B	0.7553	0.5612	0.7853	0.061*
C2	0.56313 (14)	0.60008 (11)	0.84772 (9)	0.0461 (3)
C3	0.61877 (16)	0.61816 (12)	0.93888 (10)	0.0552 (4)
C4	0.53887 (19)	0.68481 (15)	1.01131 (11)	0.0697 (5)
H4A	0.5969	0.6995	1.0593	0.105*
H4B	0.4616	0.6460	1.0400	0.105*
H4C	0.5067	0.7518	0.9813	0.105*
C5	0.43370 (14)	0.63270 (11)	0.83276 (10)	0.0482 (3)
H5	0.3868	0.6720	0.8806	0.058*
C6	0.35438 (15)	0.61632 (12)	0.75311 (10)	0.0525 (3)
C7	0.37769 (18)	0.52938 (13)	0.69523 (11)	0.0614 (4)
H7	0.4502	0.4793	0.7047	0.074*
C8	0.2945 (2)	0.51655 (16)	0.62389 (13)	0.0760 (5)
H8	0.3118	0.4582	0.5857	0.091*
C9	0.1871 (2)	0.58891 (19)	0.60901 (14)	0.0851 (6)
H9	0.1307	0.5793	0.5614	0.102*
C10	0.1628 (2)	0.67582 (19)	0.66457 (15)	0.0836 (6)
H10	0.0908	0.7259	0.6536	0.100*
C11	0.24423 (17)	0.68949 (16)	0.73662 (13)	0.0680 (4)
H11	0.2256	0.7480	0.7746	0.082*
C12	0.73601 (14)	0.36282 (11)	0.74086 (9)	0.0462 (3)
C13	0.83798 (14)	0.39762 (11)	0.67315 (9)	0.0450 (3)
H13	0.8479	0.4709	0.6573	0.054*
C14	0.92491 (13)	0.31981 (11)	0.62973 (9)	0.0415 (3)
C15	1.11843 (15)	0.29105 (12)	0.51475 (10)	0.0491 (3)
C16	1.10802 (15)	0.17735 (12)	0.53629 (10)	0.0507 (3)
H16	1.1712	0.1300	0.5048	0.061*
C17	1.01082 (15)	0.13580 (11)	0.60016 (9)	0.0469 (3)
C18	0.91298 (14)	0.20950 (11)	0.64932 (9)	0.0430 (3)
C19	0.80687 (15)	0.17767 (11)	0.71703 (10)	0.0506 (3)
H19	0.7950	0.1044	0.7317	0.061*
C20	0.72030 (16)	0.25230 (12)	0.76206 (10)	0.0526 (4)
H20	0.6505	0.2295	0.8071	0.063*
C21	1.00109 (18)	0.01671 (12)	0.62083 (11)	0.0619 (4)
H21A	1.0740	−0.0209	0.5839	0.093*
H21B	0.9139	−0.0050	0.6048	0.093*
H21C	1.0090	−0.0005	0.6871	0.093*
C22	1.42046 (16)	0.01415 (12)	0.66110 (11)	0.0550 (4)
H22A	1.4946	0.0503	0.6846	0.066*
H22B	1.3872	0.0585	0.6084	0.066*
C23	1.47095 (15)	−0.09526 (11)	0.62931 (10)	0.0494 (3)
C24	1.40983 (15)	−0.12992 (12)	0.54516 (10)	0.0534 (4)
C25	1.45639 (18)	−0.23594 (13)	0.50425 (11)	0.0636 (4)
H25A	1.5537	−0.2367	0.4862	0.095*
H25B	1.4088	−0.2450	0.4494	0.095*
H25C	1.4364	−0.2939	0.5509	0.095*
C26	1.56948 (14)	−0.15546 (11)	0.66955 (10)	0.0485 (3)
H26	1.5945	−0.2206	0.6420	0.058*
C27	1.64397 (16)	−0.13415 (12)	0.75052 (10)	0.0531 (4)
C28	1.59257 (19)	−0.06977 (15)	0.82394 (11)	0.0681 (4)
H28	1.5032	−0.0395	0.8250	0.082*
C29	1.6727 (2)	−0.05022 (17)	0.89526 (13)	0.0841 (6)
H29	1.6376	−0.0057	0.9431	0.101*
C30	1.8031 (2)	−0.0959 (2)	0.89606 (15)	0.0893 (6)
H30	1.8573	−0.0813	0.9436	0.107*
C31	1.8537 (2)	−0.16322 (19)	0.82661 (15)	0.0864 (6)
H31	1.9413	−0.1961	0.8282	0.104*
C32	1.77542 (17)	−0.18246 (15)	0.75440 (13)	0.0671 (4)
H32	1.8109	−0.2283	0.7076	0.081*
C33	1.24785 (15)	0.08942 (11)	0.77207 (9)	0.0476 (3)
C34	1.13865 (15)	0.07032 (11)	0.83951 (9)	0.0479 (3)
H34	1.1158	−0.0001	0.8588	0.057*
C35	1.06426 (14)	0.15711 (11)	0.87758 (9)	0.0433 (3)
C36	0.87152 (16)	0.21257 (12)	0.98414 (10)	0.0538 (4)
C37	0.90271 (15)	0.32257 (12)	0.95757 (10)	0.0526 (4)
H37	0.8461	0.3775	0.9843	0.063*
C38	1.00978 (14)	0.34977 (11)	0.89585 (9)	0.0464 (3)
C39	1.09595 (14)	0.26388 (11)	0.85298 (9)	0.0435 (3)
C40	1.20862 (15)	0.27995 (12)	0.78721 (10)	0.0515 (3)
H40	1.2339	0.3502	0.7700	0.062*
C41	1.28442 (15)	0.19480 (12)	0.74656 (10)	0.0539 (4)
H41	1.3594	0.2078	0.7024	0.065*
C42	1.04227 (17)	0.46471 (12)	0.87027 (12)	0.0605 (4)
H42A	1.1304	0.4780	0.8904	0.091*
H42B	0.9730	0.5117	0.9012	0.091*
H42C	1.0444	0.4784	0.8028	0.091*
O1	0.72972 (14)	0.57721 (13)	0.95517 (10)	0.0940 (5)
O2	0.64601 (10)	0.42965 (8)	0.79142 (7)	0.0555 (3)
O3	1.02571 (10)	0.35905 (7)	0.56416 (6)	0.0474 (2)
O4	1.20006 (12)	0.33432 (9)	0.45684 (8)	0.0693 (3)
O5	1.32377 (13)	−0.07151 (11)	0.50820 (9)	0.0787 (4)
O6	1.31154 (11)	−0.00128 (8)	0.73480 (7)	0.0594 (3)
O7	0.95511 (10)	0.13252 (8)	0.94262 (7)	0.0516 (3)
O8	0.77875 (13)	0.18204 (10)	1.04032 (9)	0.0789 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0502 (8)	0.0476 (8)	0.0527 (8)	0.0014 (6)	0.0055 (6)	−0.0058 (6)
C2	0.0466 (8)	0.0448 (7)	0.0451 (7)	0.0007 (6)	0.0036 (6)	−0.0037 (6)
C3	0.0535 (9)	0.0591 (9)	0.0517 (8)	0.0054 (7)	−0.0029 (7)	−0.0043 (7)
C4	0.0750 (11)	0.0830 (12)	0.0516 (9)	0.0060 (9)	−0.0045 (8)	−0.0195 (8)
C5	0.0473 (8)	0.0498 (8)	0.0459 (7)	0.0000 (6)	0.0043 (6)	−0.0048 (6)
C6	0.0475 (8)	0.0588 (8)	0.0501 (8)	−0.0086 (7)	−0.0001 (6)	0.0018 (6)
C7	0.0688 (10)	0.0556 (9)	0.0614 (9)	−0.0117 (8)	−0.0117 (8)	0.0001 (7)
C8	0.0943 (14)	0.0721 (11)	0.0664 (11)	−0.0254 (10)	−0.0215 (10)	−0.0011 (9)
C9	0.0848 (14)	0.1025 (16)	0.0728 (12)	−0.0271 (12)	−0.0317 (11)	0.0141 (11)
C10	0.0601 (11)	0.1067 (16)	0.0838 (13)	0.0014 (10)	−0.0202 (10)	0.0108 (12)
C11	0.0510 (9)	0.0832 (12)	0.0686 (10)	0.0031 (8)	−0.0048 (8)	−0.0026 (9)
C12	0.0500 (8)	0.0476 (7)	0.0399 (7)	0.0048 (6)	−0.0011 (6)	−0.0051 (6)
C13	0.0512 (8)	0.0406 (7)	0.0422 (7)	0.0022 (6)	−0.0011 (6)	−0.0034 (5)
C14	0.0437 (7)	0.0458 (7)	0.0353 (6)	−0.0009 (5)	−0.0051 (5)	−0.0047 (5)
C15	0.0453 (8)	0.0547 (8)	0.0476 (7)	0.0017 (6)	−0.0002 (6)	−0.0146 (6)
C16	0.0503 (8)	0.0521 (8)	0.0507 (8)	0.0068 (6)	−0.0059 (6)	−0.0172 (6)
C17	0.0548 (8)	0.0447 (7)	0.0435 (7)	0.0034 (6)	−0.0144 (6)	−0.0114 (6)
C18	0.0499 (8)	0.0427 (7)	0.0378 (6)	0.0012 (6)	−0.0096 (6)	−0.0069 (5)
C19	0.0637 (9)	0.0408 (7)	0.0470 (7)	−0.0049 (6)	−0.0038 (6)	−0.0020 (6)
C20	0.0585 (9)	0.0526 (8)	0.0445 (7)	−0.0051 (7)	0.0059 (6)	−0.0012 (6)
C21	0.0819 (11)	0.0447 (8)	0.0599 (9)	0.0044 (7)	−0.0084 (8)	−0.0116 (7)
C22	0.0587 (9)	0.0510 (8)	0.0519 (8)	0.0034 (7)	0.0086 (7)	−0.0032 (6)
C23	0.0497 (8)	0.0493 (8)	0.0472 (7)	0.0031 (6)	0.0048 (6)	−0.0064 (6)
C24	0.0510 (8)	0.0594 (9)	0.0479 (8)	0.0018 (7)	0.0037 (6)	−0.0053 (7)
C25	0.0733 (11)	0.0645 (10)	0.0535 (9)	−0.0042 (8)	−0.0001 (8)	−0.0151 (7)
C26	0.0494 (8)	0.0457 (7)	0.0487 (8)	−0.0015 (6)	0.0044 (6)	−0.0050 (6)
C27	0.0550 (9)	0.0509 (8)	0.0526 (8)	−0.0075 (7)	−0.0026 (7)	0.0028 (6)
C28	0.0751 (11)	0.0753 (11)	0.0539 (9)	−0.0009 (9)	−0.0068 (8)	−0.0065 (8)
C29	0.1088 (17)	0.0907 (14)	0.0555 (10)	−0.0165 (12)	−0.0136 (10)	−0.0068 (9)
C30	0.0939 (16)	0.1127 (17)	0.0658 (12)	−0.0307 (13)	−0.0284 (11)	0.0124 (11)
C31	0.0666 (12)	0.1114 (17)	0.0821 (13)	−0.0081 (11)	−0.0208 (10)	0.0113 (12)
C32	0.0590 (10)	0.0730 (11)	0.0685 (10)	−0.0027 (8)	−0.0073 (8)	0.0041 (8)
C33	0.0518 (8)	0.0474 (7)	0.0426 (7)	0.0075 (6)	−0.0010 (6)	−0.0086 (6)
C34	0.0550 (8)	0.0432 (7)	0.0439 (7)	0.0044 (6)	−0.0006 (6)	−0.0037 (6)
C35	0.0454 (7)	0.0492 (7)	0.0348 (6)	0.0043 (6)	−0.0035 (5)	−0.0045 (5)
C36	0.0536 (9)	0.0573 (9)	0.0480 (8)	0.0108 (7)	0.0037 (7)	−0.0078 (6)
C37	0.0534 (8)	0.0515 (8)	0.0526 (8)	0.0113 (7)	−0.0036 (7)	−0.0145 (6)
C38	0.0500 (8)	0.0467 (7)	0.0441 (7)	0.0063 (6)	−0.0118 (6)	−0.0104 (6)
C39	0.0477 (8)	0.0450 (7)	0.0385 (7)	0.0036 (6)	−0.0086 (6)	−0.0076 (5)
C40	0.0570 (9)	0.0459 (8)	0.0511 (8)	−0.0029 (6)	−0.0004 (7)	−0.0054 (6)
C41	0.0533 (8)	0.0579 (9)	0.0486 (8)	−0.0013 (7)	0.0061 (6)	−0.0073 (6)
C42	0.0666 (10)	0.0456 (8)	0.0698 (10)	0.0040 (7)	−0.0065 (8)	−0.0132 (7)
O1	0.0745 (9)	0.1308 (12)	0.0787 (9)	0.0390 (8)	−0.0274 (7)	−0.0288 (8)
O2	0.0588 (6)	0.0479 (6)	0.0549 (6)	0.0049 (5)	0.0153 (5)	−0.0027 (4)
O3	0.0486 (5)	0.0452 (5)	0.0469 (5)	0.0001 (4)	0.0050 (4)	−0.0069 (4)
O4	0.0645 (7)	0.0653 (7)	0.0735 (7)	−0.0037 (6)	0.0229 (6)	−0.0136 (6)
O5	0.0785 (8)	0.0898 (9)	0.0687 (8)	0.0230 (7)	−0.0204 (6)	−0.0139 (6)
O6	0.0631 (7)	0.0521 (6)	0.0587 (6)	0.0062 (5)	0.0151 (5)	−0.0088 (5)
O7	0.0554 (6)	0.0472 (5)	0.0487 (5)	0.0064 (4)	0.0075 (4)	−0.0035 (4)
O8	0.0771 (8)	0.0693 (8)	0.0805 (8)	0.0095 (6)	0.0320 (7)	−0.0023 (6)

Geometric parameters (Å, º) top

C1—O2	1.4387 (17)	C22—O6	1.4281 (17)
C1—C2	1.4956 (18)	C22—C23	1.4992 (19)
C1—H1A	0.9700	C22—H22A	0.9700
C1—H1B	0.9700	C22—H22B	0.9700
C2—C5	1.3396 (19)	C23—C26	1.336 (2)
C2—C3	1.486 (2)	C23—C24	1.484 (2)
C3—O1	1.2085 (18)	C24—O5	1.2155 (18)
C3—C4	1.493 (2)	C24—C25	1.500 (2)
C4—H4A	0.9600	C25—H25A	0.9600
C4—H4B	0.9600	C25—H25B	0.9600
C4—H4C	0.9600	C25—H25C	0.9600
C5—C6	1.463 (2)	C26—C27	1.465 (2)
C5—H5	0.9300	C26—H26	0.9300
C6—C7	1.392 (2)	C27—C28	1.390 (2)
C6—C11	1.397 (2)	C27—C32	1.392 (2)
C7—C8	1.381 (2)	C28—C29	1.380 (2)
C7—H7	0.9300	C28—H28	0.9300
C8—C9	1.366 (3)	C29—C30	1.367 (3)
C8—H8	0.9300	C29—H29	0.9300
C9—C10	1.372 (3)	C30—C31	1.370 (3)
C9—H9	0.9300	C30—H30	0.9300
C10—C11	1.380 (3)	C31—C32	1.378 (3)
C10—H10	0.9300	C31—H31	0.9300
C11—H11	0.9300	C32—H32	0.9300
C12—O2	1.3586 (15)	C33—O6	1.3659 (16)
C12—C13	1.3808 (19)	C33—C34	1.381 (2)
C12—C20	1.397 (2)	C33—C41	1.390 (2)
C13—C14	1.3836 (18)	C34—C35	1.3744 (18)
C13—H13	0.9300	C34—H34	0.9300
C14—O3	1.3733 (16)	C35—O7	1.3739 (16)
C14—C18	1.3870 (19)	C35—C39	1.3908 (19)
C15—O4	1.2084 (18)	C36—O8	1.2070 (18)
C15—O3	1.3747 (16)	C36—O7	1.3748 (16)
C15—C16	1.430 (2)	C36—C37	1.432 (2)
C16—C17	1.346 (2)	C37—C38	1.340 (2)
C16—H16	0.9300	C37—H37	0.9300
C17—C18	1.4455 (18)	C38—C39	1.4479 (18)
C17—C21	1.493 (2)	C38—C42	1.491 (2)
C18—C19	1.398 (2)	C39—C40	1.386 (2)
C19—C20	1.3648 (19)	C40—C41	1.3797 (19)
C19—H19	0.9300	C40—H40	0.9300
C20—H20	0.9300	C41—H41	0.9300
C21—H21A	0.9600	C42—H42A	0.9600
C21—H21B	0.9600	C42—H42B	0.9600
C21—H21C	0.9600	C42—H42C	0.9600

O2—C1—C2	108.32 (11)	C23—C22—H22A	110.2
O2—C1—H1A	110.0	O6—C22—H22B	110.2
C2—C1—H1A	110.0	C23—C22—H22B	110.2
O2—C1—H1B	110.0	H22A—C22—H22B	108.5
C2—C1—H1B	110.0	C26—C23—C24	121.63 (13)
H1A—C1—H1B	108.4	C26—C23—C22	123.12 (13)
C5—C2—C3	120.75 (12)	C24—C23—C22	115.14 (13)
C5—C2—C1	124.21 (13)	O5—C24—C23	120.00 (14)
C3—C2—C1	115.04 (12)	O5—C24—C25	119.89 (14)
O1—C3—C2	119.53 (14)	C23—C24—C25	120.09 (13)
O1—C3—C4	119.44 (14)	C24—C25—H25A	109.5
C2—C3—C4	121.03 (13)	C24—C25—H25B	109.5
C3—C4—H4A	109.5	H25A—C25—H25B	109.5
C3—C4—H4B	109.5	C24—C25—H25C	109.5
H4A—C4—H4B	109.5	H25A—C25—H25C	109.5
C3—C4—H4C	109.5	H25B—C25—H25C	109.5
H4A—C4—H4C	109.5	C23—C26—C27	129.65 (13)
H4B—C4—H4C	109.5	C23—C26—H26	115.2
C2—C5—C6	130.26 (13)	C27—C26—H26	115.2
C2—C5—H5	114.9	C28—C27—C32	117.74 (15)
C6—C5—H5	114.9	C28—C27—C26	124.75 (14)
C7—C6—C11	117.75 (15)	C32—C27—C26	117.51 (14)
C7—C6—C5	124.07 (14)	C29—C28—C27	120.72 (18)
C11—C6—C5	118.12 (14)	C29—C28—H28	119.6
C8—C7—C6	120.84 (17)	C27—C28—H28	119.6
C8—C7—H7	119.6	C30—C29—C28	120.48 (19)
C6—C7—H7	119.6	C30—C29—H29	119.8
C9—C8—C7	120.53 (19)	C28—C29—H29	119.8
C9—C8—H8	119.7	C29—C30—C31	119.77 (19)
C7—C8—H8	119.7	C29—C30—H30	120.1
C8—C9—C10	119.74 (18)	C31—C30—H30	120.1
C8—C9—H9	120.1	C30—C31—C32	120.3 (2)
C10—C9—H9	120.1	C30—C31—H31	119.8
C9—C10—C11	120.50 (19)	C32—C31—H31	119.8
C9—C10—H10	119.7	C31—C32—C27	120.87 (18)
C11—C10—H10	119.7	C31—C32—H32	119.6
C10—C11—C6	120.63 (18)	C27—C32—H32	119.6
C10—C11—H11	119.7	O6—C33—C34	114.83 (12)
C6—C11—H11	119.7	O6—C33—C41	125.12 (13)
O2—C12—C13	124.43 (12)	C34—C33—C41	120.05 (12)
O2—C12—C20	115.23 (12)	C35—C34—C33	118.86 (13)
C13—C12—C20	120.34 (12)	C35—C34—H34	120.6
C12—C13—C14	117.79 (12)	C33—C34—H34	120.6
C12—C13—H13	121.1	O7—C35—C34	115.89 (12)
C14—C13—H13	121.1	O7—C35—C39	121.17 (12)
O3—C14—C13	115.28 (11)	C34—C35—C39	122.94 (13)
O3—C14—C18	121.25 (11)	O8—C36—O7	115.77 (14)
C13—C14—C18	123.47 (12)	O8—C36—C37	126.60 (13)
O4—C15—O3	115.98 (13)	O7—C36—C37	117.63 (13)
O4—C15—C16	126.84 (13)	C38—C37—C36	122.93 (13)
O3—C15—C16	117.17 (12)	C38—C37—H37	118.5
C17—C16—C15	122.92 (13)	C36—C37—H37	118.5
C17—C16—H16	118.5	C37—C38—C39	118.30 (13)
C15—C16—H16	118.5	C37—C38—C42	122.24 (13)
C16—C17—C18	118.49 (13)	C39—C38—C42	119.46 (13)
C16—C17—C21	121.99 (13)	C40—C39—C35	116.64 (12)
C18—C17—C21	119.52 (13)	C40—C39—C38	124.60 (13)
C14—C18—C19	116.91 (12)	C35—C39—C38	118.75 (13)
C14—C18—C17	118.52 (13)	C41—C40—C39	121.97 (14)
C19—C18—C17	124.56 (13)	C41—C40—H40	119.0
C20—C19—C18	121.14 (13)	C39—C40—H40	119.0
C20—C19—H19	119.4	C40—C41—C33	119.50 (13)
C18—C19—H19	119.4	C40—C41—H41	120.3
C19—C20—C12	120.32 (13)	C33—C41—H41	120.3
C19—C20—H20	119.8	C38—C42—H42A	109.5
C12—C20—H20	119.8	C38—C42—H42B	109.5
C17—C21—H21A	109.5	H42A—C42—H42B	109.5
C17—C21—H21B	109.5	C38—C42—H42C	109.5
H21A—C21—H21B	109.5	H42A—C42—H42C	109.5
C17—C21—H21C	109.5	H42B—C42—H42C	109.5
H21A—C21—H21C	109.5	C12—O2—C1	118.01 (11)
H21B—C21—H21C	109.5	C14—O3—C15	121.63 (11)
O6—C22—C23	107.67 (12)	C33—O6—C22	117.14 (11)
O6—C22—H22A	110.2	C35—O7—C36	121.20 (11)

O2—C1—C2—C5	−89.47 (16)	C22—C23—C26—C27	2.4 (2)
O2—C1—C2—C3	90.67 (15)	C23—C26—C27—C28	26.9 (3)
C5—C2—C3—O1	171.46 (16)	C23—C26—C27—C32	−153.46 (16)
C1—C2—C3—O1	−8.7 (2)	C32—C27—C28—C29	3.4 (3)
C5—C2—C3—C4	−7.6 (2)	C26—C27—C28—C29	−177.02 (16)
C1—C2—C3—C4	172.22 (14)	C27—C28—C29—C30	−1.5 (3)
C3—C2—C5—C6	−174.56 (14)	C28—C29—C30—C31	−1.3 (3)
C1—C2—C5—C6	5.6 (2)	C29—C30—C31—C32	2.0 (3)
C2—C5—C6—C7	26.7 (2)	C30—C31—C32—C27	0.0 (3)
C2—C5—C6—C11	−156.43 (16)	C28—C27—C32—C31	−2.6 (3)
C11—C6—C7—C8	0.2 (2)	C26—C27—C32—C31	177.72 (16)
C5—C6—C7—C8	177.05 (15)	O6—C33—C34—C35	−176.91 (12)
C6—C7—C8—C9	−0.3 (3)	C41—C33—C34—C35	2.6 (2)
C7—C8—C9—C10	0.9 (3)	C33—C34—C35—O7	178.55 (12)
C8—C9—C10—C11	−1.3 (3)	C33—C34—C35—C39	−1.6 (2)
C9—C10—C11—C6	1.2 (3)	O8—C36—C37—C38	178.55 (16)
C7—C6—C11—C10	−0.6 (2)	O7—C36—C37—C38	−1.0 (2)
C5—C6—C11—C10	−177.68 (16)	C36—C37—C38—C39	1.2 (2)
O2—C12—C13—C14	177.87 (12)	C36—C37—C38—C42	−178.88 (14)
C20—C12—C13—C14	−1.7 (2)	O7—C35—C39—C40	179.56 (12)
C12—C13—C14—O3	−178.97 (11)	C34—C35—C39—C40	−0.3 (2)
C12—C13—C14—C18	1.4 (2)	O7—C35—C39—C38	−1.25 (19)
O4—C15—C16—C17	−177.92 (15)	C34—C35—C39—C38	178.93 (12)
O3—C15—C16—C17	1.6 (2)	C37—C38—C39—C40	179.06 (13)
C15—C16—C17—C18	−0.2 (2)	C42—C38—C39—C40	−0.9 (2)
C15—C16—C17—C21	179.40 (13)	C37—C38—C39—C35	−0.06 (19)
O3—C14—C18—C19	−179.87 (11)	C42—C38—C39—C35	−179.99 (12)
C13—C14—C18—C19	−0.22 (19)	C35—C39—C40—C41	1.2 (2)
O3—C14—C18—C17	0.99 (18)	C38—C39—C40—C41	−177.95 (13)
C13—C14—C18—C17	−179.35 (12)	C39—C40—C41—C33	−0.2 (2)
C16—C17—C18—C14	−1.07 (19)	O6—C33—C41—C40	177.74 (13)
C21—C17—C18—C14	179.32 (12)	C34—C33—C41—C40	−1.7 (2)
C16—C17—C18—C19	179.86 (13)	C13—C12—O2—C1	−3.1 (2)
C21—C17—C18—C19	0.3 (2)	C20—C12—O2—C1	176.50 (12)
C14—C18—C19—C20	−0.6 (2)	C2—C1—O2—C12	−173.35 (12)
C17—C18—C19—C20	178.49 (13)	C13—C14—O3—C15	−179.27 (11)
C18—C19—C20—C12	0.2 (2)	C18—C14—O3—C15	0.42 (18)
O2—C12—C20—C19	−178.64 (13)	O4—C15—O3—C14	177.88 (12)
C13—C12—C20—C19	1.0 (2)	C16—C15—O3—C14	−1.65 (18)
O6—C22—C23—C26	−88.27 (17)	C34—C33—O6—C22	176.75 (12)
O6—C22—C23—C24	95.48 (15)	C41—C33—O6—C22	−2.7 (2)
C26—C23—C24—O5	−177.42 (15)	C23—C22—O6—C33	−178.10 (12)
C22—C23—C24—O5	−1.1 (2)	C34—C35—O7—C36	−178.73 (12)
C26—C23—C24—C25	1.2 (2)	C39—C35—O7—C36	1.44 (19)
C22—C23—C24—C25	177.53 (13)	O8—C36—O7—C35	−179.95 (13)
C24—C23—C26—C27	178.41 (14)	C37—C36—O7—C35	−0.3 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is centroid of the C6–C11 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O8ⁱ	0.93	2.59	3.4778 (19)	159
C9—H9···O3ⁱⁱ	0.93	2.52	3.381 (2)	155
C30—H30···O7ⁱⁱⁱ	0.93	2.59	3.441 (2)	153
C42—H42B···O1	0.96	2.53	3.427 (2)	155
C25—H25C···Cg1^iv	0.96	2.64	3.5238 (18)	152

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

Hydrogen-bond geometry (Å, º) top

Cg1 is centroid of the C6–C11 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O8ⁱ	0.93	2.59	3.4778 (19)	159
C9—H9···O3ⁱⁱ	0.93	2.52	3.381 (2)	155
C30—H30···O7ⁱⁱⁱ	0.93	2.59	3.441 (2)	153
C42—H42B···O1	0.96	2.53	3.427 (2)	155
C25—H25C···Cg1^iv	0.96	2.64	3.5238 (18)	152

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

Acknowledgements

We thank Professor Regina H. A. Santos from IQSC–USP for the X-ray data collection. The Brazilian agencies CNPq (306121/2013-2 to IC, 305626/2013-2 to JZS and 304730/2013-0 to PJSM), FAPESP (2012/08385-6 to BRSP) and CAPES are acknowledged for financial support.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burla, M. C., Caliandro, R., Carrozzini, B., Cascarano, G. L., Cuocci, C., Giacovazzo, C., Mallamo, M., Mazzone, A. & Polidori, G. (2015). J. Appl. Cryst. 48, 306–309. Web of Science CrossRef CAS IUCr Journals Google Scholar
ChemAxon (2010). Marvinsketch. https://www.chemaxon.com. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557–559. Web of Science CrossRef PubMed CAS Google Scholar
Paula, B. R. S. de, Zampieri, D. S., Rodrigues, J. A. R. & Moran, P. J. S. (2013). Tetrahedron Asymmetry, 24, 973–981. Google Scholar
Seth, S. K., Sarkar, D., JANA, A. D. & Kar, T. (2011). Cryst. Growth Des. 11, 4837–4849. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zukerman-Schpector, J., Maganhi, S. H., Moran, P. J. S., Paula, B. R. S. de, Nucci, P. R. & Tiekink, E. R. T. (2014). Acta Cryst. E70, o1020–o1021. CSD CrossRef IUCr Journals Google Scholar

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Volume 71| Part 4| April 2015| Pages o222-o223

doi:10.1107/S2056989015003084

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 7-[(2E)-2-benzyl­­idene-3-oxobut­­oxy]-4-methyl-2H-chromen-2-one

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 7-[(2E)-2-benzylidene-3-oxobutoxy]-4-methyl-2H-chromen-2-one