Ethyl 2,5-diphenyl­furan-3-carboxyl­ate

Meng, X.-G.; Wu, A.

doi:10.1107/S1600536805024554

Ethyl 2,5-diphenylfuran-3-carboxylate

In the title compound, C₁₉H₁₆O₃, the dihedral between the two phenyl rings is 12.6 (1)°. An intramolecular hydrogen bond and weak C—H

π interactions are observed.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805024554/is6110sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805024554/is6110Isup2.hkl Contains datablock I

CCDC reference: 283939

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.002 Å
R factor = 0.043
wR factor = 0.119
Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H13    ..  CG1     ..       3.26 Ang.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H18B   ..  CG1     ..       3.01 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19C   ..  CG2     ..       2.91 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Ethyl 2,5-diphenylfuran-3-carboxylate top

Crystal data top

C₁₉H₁₆O₃	F(000) = 1232
M_r = 292.32	D_x = 1.258 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5225 reflections
a = 9.6272 (9) Å	θ = 2.3–25.1°
b = 15.0692 (14) Å	µ = 0.08 mm⁻¹
c = 21.2860 (19) Å	T = 292 K
V = 3088.1 (5) Å³	Block, colorless
Z = 8	0.30 × 0.20 × 0.10 mm

Data collection top

Bruker SMART Apex CCD area-detector diffractometer	3375 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	2544 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 27.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→12
T_min = 0.975, T_max = 0.992	k = −19→18
17087 measured reflections	l = −22→27

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: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0561P)² + 0.433P] where P = (F_o² + 2F_c²)/3
3375 reflections	(Δ/σ)_max < 0.001
200 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

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	1.24269 (17)	0.18591 (11)	0.31567 (7)	0.0627 (4)
H1	1.1890	0.1466	0.2923	0.075*
C2	1.37964 (18)	0.19904 (13)	0.29991 (8)	0.0716 (5)
H2	1.4175	0.1682	0.2662	0.086*
C3	1.46099 (17)	0.25672 (12)	0.33303 (8)	0.0693 (5)
H3	1.5536	0.2651	0.3222	0.083*
C4	1.40402 (18)	0.30185 (12)	0.38242 (9)	0.0768 (5)
H4	1.4585	0.3414	0.4052	0.092*
C5	1.26665 (17)	0.28955 (11)	0.39897 (8)	0.0678 (4)
H5	1.2296	0.3211	0.4326	0.081*
C6	1.18343 (14)	0.23074 (9)	0.36609 (6)	0.0486 (3)
C7	1.03913 (14)	0.21243 (9)	0.38364 (6)	0.0460 (3)
C8	0.93863 (14)	0.24793 (9)	0.42186 (6)	0.0461 (3)
C9	0.81727 (15)	0.19526 (9)	0.41410 (6)	0.0497 (3)
H9	0.7322	0.2041	0.4338	0.060*
C10	0.84793 (14)	0.13036 (9)	0.37300 (6)	0.0472 (3)
C11	0.76981 (15)	0.05558 (9)	0.34725 (6)	0.0487 (3)
C12	0.82819 (17)	−0.00370 (11)	0.30504 (7)	0.0633 (4)
H12	0.9201	0.0033	0.2925	0.076*
C13	0.7502 (2)	−0.07313 (11)	0.28147 (8)	0.0719 (5)
H13	0.7897	−0.1122	0.2528	0.086*
C14	0.61507 (19)	−0.08493 (11)	0.30002 (8)	0.0687 (5)
H14	0.5634	−0.1321	0.2842	0.082*
C15	0.55654 (18)	−0.02689 (12)	0.34198 (8)	0.0669 (4)
H15	0.4649	−0.0347	0.3546	0.080*
C16	0.63299 (16)	0.04297 (10)	0.36553 (7)	0.0590 (4)
H16	0.5924	0.0820	0.3939	0.071*
C17	0.94521 (14)	0.32516 (10)	0.46448 (7)	0.0493 (3)
C18	0.80942 (16)	0.42996 (10)	0.51915 (8)	0.0627 (4)
H18A	0.8738	0.4763	0.5069	0.075*
H18B	0.8322	0.4110	0.5615	0.075*
C19	0.66425 (18)	0.46325 (12)	0.51651 (9)	0.0744 (5)
H19A	0.6450	0.4854	0.4751	0.112*
H19B	0.6526	0.5101	0.5466	0.112*
H19C	0.6013	0.4157	0.5261	0.112*
O1	0.98296 (10)	0.14023 (6)	0.35345 (4)	0.0495 (3)
O2	1.04789 (11)	0.35687 (8)	0.48739 (6)	0.0712 (4)
O3	0.81832 (10)	0.35578 (6)	0.47600 (5)	0.0562 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0588 (9)	0.0743 (11)	0.0550 (8)	−0.0020 (8)	0.0037 (7)	−0.0096 (8)
C2	0.0635 (11)	0.0898 (13)	0.0614 (10)	0.0029 (9)	0.0149 (8)	−0.0084 (9)
C3	0.0524 (9)	0.0775 (11)	0.0779 (11)	−0.0005 (8)	0.0115 (8)	0.0078 (9)
C4	0.0592 (11)	0.0765 (12)	0.0946 (13)	−0.0136 (9)	0.0073 (9)	−0.0187 (10)
C5	0.0597 (10)	0.0674 (10)	0.0765 (11)	−0.0057 (8)	0.0105 (8)	−0.0190 (8)
C6	0.0505 (8)	0.0484 (8)	0.0470 (7)	0.0040 (6)	0.0011 (6)	0.0049 (6)
C7	0.0524 (8)	0.0414 (7)	0.0442 (7)	0.0024 (6)	−0.0040 (6)	0.0017 (6)
C8	0.0484 (7)	0.0432 (7)	0.0467 (7)	0.0021 (6)	−0.0017 (6)	−0.0001 (6)
C9	0.0499 (8)	0.0494 (8)	0.0499 (8)	0.0005 (6)	0.0016 (6)	−0.0035 (6)
C10	0.0491 (8)	0.0472 (8)	0.0454 (7)	0.0006 (6)	0.0010 (6)	−0.0001 (6)
C11	0.0565 (8)	0.0444 (7)	0.0451 (7)	−0.0002 (6)	−0.0035 (6)	0.0000 (6)
C12	0.0648 (10)	0.0588 (9)	0.0665 (10)	−0.0025 (8)	0.0044 (8)	−0.0134 (8)
C13	0.0846 (13)	0.0578 (9)	0.0734 (10)	0.0007 (9)	−0.0007 (9)	−0.0200 (8)
C14	0.0806 (12)	0.0556 (10)	0.0698 (10)	−0.0127 (8)	−0.0157 (9)	−0.0067 (8)
C15	0.0635 (10)	0.0664 (10)	0.0709 (10)	−0.0125 (8)	−0.0023 (8)	−0.0058 (8)
C16	0.0602 (9)	0.0576 (9)	0.0592 (9)	−0.0021 (7)	0.0013 (7)	−0.0086 (7)
C17	0.0488 (8)	0.0479 (8)	0.0513 (8)	0.0012 (6)	0.0006 (6)	−0.0036 (6)
C18	0.0618 (10)	0.0480 (8)	0.0782 (10)	−0.0015 (7)	0.0121 (8)	−0.0159 (8)
C19	0.0679 (11)	0.0583 (10)	0.0970 (13)	0.0091 (8)	0.0215 (9)	−0.0034 (9)
O1	0.0531 (6)	0.0483 (5)	0.0471 (5)	−0.0006 (4)	0.0013 (4)	−0.0054 (4)
O2	0.0518 (7)	0.0782 (8)	0.0835 (8)	0.0020 (5)	−0.0072 (5)	−0.0337 (6)
O3	0.0490 (6)	0.0503 (6)	0.0692 (6)	0.0006 (4)	0.0045 (5)	−0.0142 (5)

Geometric parameters (Å, º) top

C1—C2	1.375 (2)	C11—C12	1.386 (2)
C1—C6	1.391 (2)	C11—C16	1.387 (2)
C1—H1	0.9300	C12—C13	1.382 (2)
C2—C3	1.366 (2)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.371 (2)
C3—C4	1.367 (2)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.371 (2)
C4—C5	1.381 (2)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.379 (2)
C5—C6	1.385 (2)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.4648 (19)	C17—O2	1.2014 (16)
C7—C8	1.3725 (18)	C17—O3	1.3286 (16)
C7—O1	1.3745 (16)	C18—O3	1.4494 (17)
C8—C9	1.4222 (19)	C18—C19	1.486 (2)
C8—C17	1.4770 (19)	C18—H18A	0.9700
C9—C10	1.3449 (19)	C18—H18B	0.9700
C9—H9	0.9300	C19—H19A	0.9600
C10—O1	1.3730 (16)	C19—H19B	0.9600
C10—C11	1.4615 (19)	C19—H19C	0.9600

C2—C1—C6	120.79 (15)	C13—C12—C11	120.18 (16)
C2—C1—H1	119.6	C13—C12—H12	119.9
C6—C1—H1	119.6	C11—C12—H12	119.9
C3—C2—C1	121.03 (16)	C14—C13—C12	120.62 (16)
C3—C2—H2	119.5	C14—C13—H13	119.7
C1—C2—H2	119.5	C12—C13—H13	119.7
C2—C3—C4	118.91 (16)	C13—C14—C15	119.65 (15)
C2—C3—H3	120.5	C13—C14—H14	120.2
C4—C3—H3	120.5	C15—C14—H14	120.2
C3—C4—C5	120.90 (17)	C14—C15—C16	120.30 (16)
C3—C4—H4	119.5	C14—C15—H15	119.8
C5—C4—H4	119.5	C16—C15—H15	119.8
C4—C5—C6	120.73 (16)	C15—C16—C11	120.64 (15)
C4—C5—H5	119.6	C15—C16—H16	119.7
C6—C5—H5	119.6	C11—C16—H16	119.7
C5—C6—C1	117.62 (14)	O2—C17—O3	122.92 (13)
C5—C6—C7	122.71 (13)	O2—C17—C8	126.73 (13)
C1—C6—C7	119.64 (13)	O3—C17—C8	110.34 (11)
C8—C7—O1	107.96 (12)	O3—C18—C19	106.98 (13)
C8—C7—C6	138.27 (13)	O3—C18—H18A	110.3
O1—C7—C6	113.76 (12)	C19—C18—H18A	110.3
C7—C8—C9	107.02 (12)	O3—C18—H18B	110.3
C7—C8—C17	129.86 (13)	C19—C18—H18B	110.3
C9—C8—C17	123.12 (12)	H18A—C18—H18B	108.6
C10—C9—C8	107.52 (12)	C18—C19—H19A	109.5
C10—C9—H9	126.2	C18—C19—H19B	109.5
C8—C9—H9	126.2	H19A—C19—H19B	109.5
C9—C10—O1	109.04 (12)	C18—C19—H19C	109.5
C9—C10—C11	133.76 (13)	H19A—C19—H19C	109.5
O1—C10—C11	117.19 (12)	H19B—C19—H19C	109.5
C12—C11—C16	118.61 (13)	C10—O1—C7	108.45 (10)
C12—C11—C10	122.10 (14)	C17—O3—C18	116.05 (11)
C16—C11—C10	119.29 (13)

C6—C1—C2—C3	−0.4 (3)	C9—C10—C11—C16	0.7 (2)
C1—C2—C3—C4	−0.2 (3)	O1—C10—C11—C16	−179.90 (12)
C2—C3—C4—C5	0.2 (3)	C16—C11—C12—C13	0.7 (2)
C3—C4—C5—C6	0.4 (3)	C10—C11—C12—C13	−179.49 (14)
C4—C5—C6—C1	−0.9 (2)	C11—C12—C13—C14	−0.8 (3)
C4—C5—C6—C7	177.12 (16)	C12—C13—C14—C15	0.5 (3)
C2—C1—C6—C5	0.9 (2)	C13—C14—C15—C16	−0.1 (3)
C2—C1—C6—C7	−177.18 (14)	C14—C15—C16—C11	0.0 (3)
C5—C6—C7—C8	13.6 (3)	C12—C11—C16—C15	−0.3 (2)
C1—C6—C7—C8	−168.49 (16)	C10—C11—C16—C15	179.90 (14)
C5—C6—C7—O1	−167.86 (13)	C7—C8—C17—O2	−22.7 (3)
C1—C6—C7—O1	10.06 (18)	C9—C8—C17—O2	157.10 (15)
O1—C7—C8—C9	−0.26 (14)	C7—C8—C17—O3	158.58 (13)
C6—C7—C8—C9	178.34 (15)	C9—C8—C17—O3	−21.64 (19)
O1—C7—C8—C17	179.54 (13)	C9—C10—O1—C7	0.80 (14)
C6—C7—C8—C17	−1.9 (3)	C11—C10—O1—C7	−178.73 (11)
C7—C8—C9—C10	0.75 (15)	C8—C7—O1—C10	−0.31 (14)
C17—C8—C9—C10	−179.07 (13)	C6—C7—O1—C10	−179.30 (11)
C8—C9—C10—O1	−0.95 (15)	O2—C17—O3—C18	−0.9 (2)
C8—C9—C10—C11	178.47 (14)	C8—C17—O3—C18	177.90 (12)
C9—C10—C11—C12	−179.13 (15)	C19—C18—O3—C17	170.23 (13)
O1—C10—C11—C12	0.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2	0.93	2.17	3.001 (2)	148
C13—H13···Cg1ⁱ	0.93	3.26	3.981 (1)	136
C18—H18B···Cg1ⁱⁱ	0.97	3.01	3.837 (1)	144
C19—H19C···Cg2ⁱⁱ	0.96	2.91	3.786 (1)	153

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

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Ethyl 2,5-diphenyl­furan-3-carboxyl­ate

Supporting information

Key indicators

checkCIF/PLATON results

Ethyl 2,5-diphenylfuran-3-carboxylate