Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026554/at2314sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026554/at2314Isup2.hkl |
CCDC reference: 654942
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.041
- wR factor = 0.110
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.72 mm PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Explicit -P 2yc PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. O1 .. 2.85 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. O1 .. 2.65 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. O3 .. 2.83 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A pure sample of the compound was obtained from Alfa Aeser GmbH & Co KG, Germany, and crystallized by slow evaporation of a solution in ethyl DMF-H2O (1:1 v/v) solution at room temperature, m.p. 425–425 K.
H atoms were placed in idealized positions with d(C—H) = 0.93 for aromatic, d(C—H) = 0.98 Å for methine and d(C—O)=0.82 Å for hydroxy and thereafter treated as riding. Uiso for H was assigned as 1.2 times Ueq of the attached C atoms (1.5 for O)
The present work is part of a structural study of carbonyl compounds (Odabaşoğlu & Büyükgüngör, 2006) and we report here the structure of 3-(4-ethoxyanilino)isobenzofuran-1(3H)-one, (I), Fig. 1, Table 1. The dihedral angle between aromatic rings is 88.07 (11)°. The bond lengths and angles are in normal ranges, and comparable with in our previous work on carbonyl compounds (Büyükgüngör & Odabaşoğlu, 2006; Odabaşoğlu & Büyükgüngör, 2006; Odabaşoğlu et al., 2006; Odabaşoğlu et al., 2005; Ersanlı et al., 2005; Allen et al., 1987). The C2—O1 bond distance in (I) is also consistent with the value of the C=O double bond in carbonyl compounds (Loudon, 2002).
The title compound, I, are stabilized by one O—H···O, three C—H···O intermolecular hydrogen bonds and one C—H···π interactions. O—H···O hydrogen bonds generate centrocymmetric dimers. O—H···O and two C—H···O hydrogenbonds generate spirocyclic R22(8)R21(5) ring motifs (Etter, 1990) these motifs are connected by C(6) chains and C—H···π interactions (Fig. 2 and 3).
For related structures, see: Allen et al. (1987); Odabaşoğlu et al. (2005); Büyükgüngör & Odabaşoğlu (2006); Odabaşoğlu & Büyükgüngör (2006); Odabaşoğlu et al. (2006); Ersanlı et al. (2005); Etter (1990); Loudon (2002); Sheldrick (1990).
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C14H9ClO3 | F(000) = 536 |
Mr = 260.66 | Dx = 1.394 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yc | Cell parameters from 6666 reflections |
a = 15.3209 (17) Å | θ = 2.1–27.9° |
b = 7.3171 (6) Å | µ = 0.30 mm−1 |
c = 11.1988 (14) Å | T = 296 K |
β = 98.467 (10)° | Prism, colorless |
V = 1241.8 (2) Å3 | 0.72 × 0.44 × 0.27 mm |
Z = 4 |
Stoe IPDSII diffractometer | 2381 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1611 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.030 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 3.1° |
ω scans | h = −18→15 |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | k = −9→9 |
Tmin = 0.839, Tmax = 0.919 | l = −13→13 |
6666 measured reflections |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0555P)2 + 0.074P] where P = (Fo2 + 2Fc2)/3 |
2381 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C14H9ClO3 | V = 1241.8 (2) Å3 |
Mr = 260.66 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.3209 (17) Å | µ = 0.30 mm−1 |
b = 7.3171 (6) Å | T = 296 K |
c = 11.1988 (14) Å | 0.72 × 0.44 × 0.27 mm |
β = 98.467 (10)° |
Stoe IPDSII diffractometer | 2381 independent reflections |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | 1611 reflections with I > 2σ(I) |
Tmin = 0.839, Tmax = 0.919 | Rint = 0.030 |
6666 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.15 e Å−3 |
2381 reflections | Δρmin = −0.26 e Å−3 |
163 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.17454 (12) | 0.0458 (2) | 0.56843 (15) | 0.0466 (4) | |
C2 | 0.10791 (12) | 0.0997 (2) | 0.47700 (15) | 0.0438 (4) | |
C3 | 0.08082 (13) | −0.0174 (2) | 0.38059 (16) | 0.0520 (5) | |
H3 | 0.0357 | 0.0182 | 0.3202 | 0.062* | |
C4 | 0.12036 (14) | −0.1853 (3) | 0.37402 (19) | 0.0585 (5) | |
H4 | 0.1027 | −0.2619 | 0.3086 | 0.070* | |
C5 | 0.18558 (16) | −0.2393 (2) | 0.46361 (19) | 0.0627 (6) | |
H5 | 0.2119 | −0.3532 | 0.4595 | 0.075* | |
C6 | 0.21235 (14) | −0.1254 (2) | 0.55999 (18) | 0.0593 (5) | |
H6 | 0.2566 | −0.1639 | 0.6206 | 0.071* | |
C7 | 0.06322 (12) | 0.2779 (2) | 0.48544 (15) | 0.0449 (4) | |
C8 | 0.20686 (13) | 0.1576 (2) | 0.67855 (16) | 0.0518 (5) | |
C9 | 0.27299 (12) | 0.3042 (2) | 0.67000 (16) | 0.0509 (5) | |
C10 | 0.31668 (15) | 0.3224 (3) | 0.5719 (2) | 0.0702 (6) | |
H10 | 0.3037 | 0.2425 | 0.5071 | 0.084* | |
C11 | 0.37936 (17) | 0.4568 (4) | 0.5675 (3) | 0.0861 (8) | |
H11 | 0.4089 | 0.4672 | 0.5009 | 0.103* | |
C12 | 0.39722 (16) | 0.5748 (3) | 0.6631 (3) | 0.0802 (7) | |
C13 | 0.35424 (16) | 0.5614 (3) | 0.7606 (2) | 0.0742 (7) | |
H13 | 0.3668 | 0.6430 | 0.8245 | 0.089* | |
C14 | 0.29228 (15) | 0.4270 (3) | 0.76445 (18) | 0.0624 (6) | |
H14 | 0.2629 | 0.4182 | 0.8312 | 0.075* | |
O1 | 0.00022 (9) | 0.31239 (18) | 0.39744 (11) | 0.0607 (4) | |
H1 | −0.0213 | 0.4126 | 0.4081 | 0.091* | |
O2 | 0.08373 (9) | 0.38031 (16) | 0.57144 (11) | 0.0551 (4) | |
O3 | 0.18427 (12) | 0.1185 (2) | 0.77436 (12) | 0.0769 (5) | |
Cl1 | 0.47438 (7) | 0.74585 (13) | 0.65780 (11) | 0.1428 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0519 (11) | 0.0417 (9) | 0.0464 (9) | 0.0039 (8) | 0.0078 (8) | 0.0043 (7) |
C2 | 0.0461 (10) | 0.0415 (8) | 0.0445 (9) | 0.0030 (7) | 0.0087 (8) | 0.0046 (7) |
C3 | 0.0540 (12) | 0.0511 (10) | 0.0504 (10) | 0.0019 (8) | 0.0059 (8) | 0.0005 (8) |
C4 | 0.0668 (14) | 0.0475 (10) | 0.0611 (12) | −0.0015 (9) | 0.0089 (10) | −0.0075 (9) |
C5 | 0.0741 (15) | 0.0390 (9) | 0.0757 (14) | 0.0078 (9) | 0.0126 (11) | −0.0009 (9) |
C6 | 0.0658 (14) | 0.0473 (10) | 0.0624 (12) | 0.0133 (9) | 0.0008 (10) | 0.0096 (9) |
C7 | 0.0468 (11) | 0.0457 (9) | 0.0424 (9) | 0.0042 (7) | 0.0074 (7) | 0.0054 (8) |
C8 | 0.0603 (13) | 0.0490 (10) | 0.0446 (10) | 0.0136 (8) | 0.0027 (9) | 0.0060 (8) |
C9 | 0.0491 (11) | 0.0557 (10) | 0.0443 (10) | 0.0116 (8) | −0.0055 (8) | −0.0032 (8) |
C10 | 0.0603 (14) | 0.0828 (15) | 0.0676 (13) | −0.0109 (12) | 0.0097 (10) | −0.0228 (11) |
C11 | 0.0650 (16) | 0.0989 (18) | 0.0979 (18) | −0.0186 (14) | 0.0237 (13) | −0.0207 (15) |
C12 | 0.0492 (14) | 0.0755 (15) | 0.112 (2) | −0.0041 (11) | −0.0013 (13) | −0.0195 (14) |
C13 | 0.0692 (16) | 0.0642 (13) | 0.0816 (15) | 0.0087 (11) | −0.0145 (12) | −0.0217 (11) |
C14 | 0.0726 (15) | 0.0596 (12) | 0.0510 (11) | 0.0146 (10) | −0.0039 (10) | −0.0042 (9) |
O1 | 0.0658 (10) | 0.0594 (7) | 0.0523 (8) | 0.0217 (7) | −0.0062 (6) | −0.0014 (6) |
O2 | 0.0574 (9) | 0.0466 (7) | 0.0574 (8) | 0.0108 (6) | −0.0048 (6) | −0.0061 (6) |
O3 | 0.1141 (14) | 0.0690 (9) | 0.0496 (8) | 0.0006 (8) | 0.0187 (8) | 0.0079 (7) |
Cl1 | 0.0970 (7) | 0.1214 (7) | 0.2131 (11) | −0.0513 (5) | 0.0328 (7) | −0.0505 (7) |
C1—C6 | 1.389 (3) | C8—O3 | 1.209 (2) |
C1—C2 | 1.392 (2) | C8—C9 | 1.488 (3) |
C1—C8 | 1.502 (2) | C9—C10 | 1.375 (3) |
C2—C3 | 1.393 (2) | C9—C14 | 1.386 (3) |
C2—C7 | 1.483 (2) | C10—C11 | 1.381 (3) |
C3—C4 | 1.377 (3) | C10—H10 | 0.9300 |
C3—H3 | 0.9300 | C11—C12 | 1.371 (3) |
C4—C5 | 1.366 (3) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C12—C13 | 1.359 (4) |
C5—C6 | 1.378 (3) | C12—Cl1 | 1.729 (3) |
C5—H5 | 0.9300 | C13—C14 | 1.372 (3) |
C6—H6 | 0.9300 | C13—H13 | 0.9300 |
C7—O2 | 1.224 (2) | C14—H14 | 0.9300 |
C7—O1 | 1.299 (2) | O1—H1 | 0.8200 |
C6—C1—C2 | 118.24 (16) | O3—C8—C1 | 119.80 (18) |
C6—C1—C8 | 117.17 (16) | C9—C8—C1 | 119.02 (16) |
C2—C1—C8 | 124.56 (15) | C10—C9—C14 | 118.2 (2) |
C1—C2—C3 | 119.93 (16) | C10—C9—C8 | 122.50 (17) |
C1—C2—C7 | 119.84 (15) | C14—C9—C8 | 119.27 (18) |
C3—C2—C7 | 120.17 (16) | C9—C10—C11 | 121.4 (2) |
C4—C3—C2 | 120.46 (18) | C9—C10—H10 | 119.3 |
C4—C3—H3 | 119.8 | C11—C10—H10 | 119.3 |
C2—C3—H3 | 119.8 | C12—C11—C10 | 118.7 (2) |
C5—C4—C3 | 119.95 (18) | C12—C11—H11 | 120.6 |
C5—C4—H4 | 120.0 | C10—C11—H11 | 120.6 |
C3—C4—H4 | 120.0 | C13—C12—C11 | 121.2 (2) |
C4—C5—C6 | 120.09 (17) | C13—C12—Cl1 | 119.6 (2) |
C4—C5—H5 | 120.0 | C11—C12—Cl1 | 119.2 (2) |
C6—C5—H5 | 120.0 | C12—C13—C14 | 119.8 (2) |
C5—C6—C1 | 121.33 (18) | C12—C13—H13 | 120.1 |
C5—C6—H6 | 119.3 | C14—C13—H13 | 120.1 |
C1—C6—H6 | 119.3 | C13—C14—C9 | 120.8 (2) |
O2—C7—O1 | 123.66 (15) | C13—C14—H14 | 119.6 |
O2—C7—C2 | 121.41 (15) | C9—C14—H14 | 119.6 |
O1—C7—C2 | 114.90 (15) | C7—O1—H1 | 109.5 |
O3—C8—C9 | 120.93 (17) | ||
C6—C1—C2—C3 | 0.1 (3) | C6—C1—C8—C9 | 99.6 (2) |
C8—C1—C2—C3 | −177.79 (17) | C2—C1—C8—C9 | −82.5 (2) |
C6—C1—C2—C7 | 177.32 (17) | O3—C8—C9—C10 | 163.2 (2) |
C8—C1—C2—C7 | −0.6 (3) | C1—C8—C9—C10 | −11.0 (3) |
C1—C2—C3—C4 | −0.9 (3) | O3—C8—C9—C14 | −16.3 (3) |
C7—C2—C3—C4 | −178.14 (17) | C1—C8—C9—C14 | 169.48 (16) |
C2—C3—C4—C5 | 1.2 (3) | C14—C9—C10—C11 | 1.1 (3) |
C3—C4—C5—C6 | −0.6 (3) | C8—C9—C10—C11 | −178.4 (2) |
C4—C5—C6—C1 | −0.3 (3) | C9—C10—C11—C12 | −0.6 (4) |
C2—C1—C6—C5 | 0.5 (3) | C10—C11—C12—C13 | −0.2 (4) |
C8—C1—C6—C5 | 178.56 (19) | C10—C11—C12—Cl1 | −179.1 (2) |
C1—C2—C7—O2 | 0.2 (3) | C11—C12—C13—C14 | 0.5 (4) |
C3—C2—C7—O2 | 177.39 (18) | Cl1—C12—C13—C14 | 179.28 (17) |
C1—C2—C7—O1 | −177.92 (16) | C12—C13—C14—C9 | 0.1 (3) |
C3—C2—C7—O1 | −0.7 (2) | C10—C9—C14—C13 | −0.9 (3) |
C6—C1—C8—O3 | −74.7 (2) | C8—C9—C14—C13 | 178.60 (18) |
C2—C1—C8—O3 | 103.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.82 | 1.82 | 2.6389 (17) | 172 |
C3—H3···O1ii | 0.93 | 2.85 | 3.413 (2) | 120 |
C4—H4···O1ii | 0.93 | 2.65 | 3.317 (2) | 129 |
C5—H5···O3iii | 0.93 | 2.83 | 3.489 (2) | 129 |
C14—H14···Cgiii | 0.93 | 2.77 | 3.592 (2) | 149 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, y−1/2, −z+1/2; (iii) x, −y−1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H9ClO3 |
Mr | 260.66 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 15.3209 (17), 7.3171 (6), 11.1988 (14) |
β (°) | 98.467 (10) |
V (Å3) | 1241.8 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.30 |
Crystal size (mm) | 0.72 × 0.44 × 0.27 |
Data collection | |
Diffractometer | Stoe IPDSII |
Absorption correction | Integration (X-RED; Stoe & Cie, 2002) |
Tmin, Tmax | 0.839, 0.919 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6666, 2381, 1611 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.110, 1.04 |
No. of reflections | 2381 |
No. of parameters | 163 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.26 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.82 | 1.82 | 2.6389 (17) | 172.2 |
C3—H3···O1ii | 0.93 | 2.85 | 3.413 (2) | 120.2 |
C4—H4···O1ii | 0.93 | 2.65 | 3.317 (2) | 128.9 |
C5—H5···O3iii | 0.93 | 2.83 | 3.489 (2) | 129.2 |
C14—H14···Cgiii | 0.93 | 2.766 | 3.592 (2) | 148.59 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, y−1/2, −z+1/2; (iii) x, −y−1/2, z−1/2. |
The present work is part of a structural study of carbonyl compounds (Odabaşoğlu & Büyükgüngör, 2006) and we report here the structure of 3-(4-ethoxyanilino)isobenzofuran-1(3H)-one, (I), Fig. 1, Table 1. The dihedral angle between aromatic rings is 88.07 (11)°. The bond lengths and angles are in normal ranges, and comparable with in our previous work on carbonyl compounds (Büyükgüngör & Odabaşoğlu, 2006; Odabaşoğlu & Büyükgüngör, 2006; Odabaşoğlu et al., 2006; Odabaşoğlu et al., 2005; Ersanlı et al., 2005; Allen et al., 1987). The C2—O1 bond distance in (I) is also consistent with the value of the C=O double bond in carbonyl compounds (Loudon, 2002).
The title compound, I, are stabilized by one O—H···O, three C—H···O intermolecular hydrogen bonds and one C—H···π interactions. O—H···O hydrogen bonds generate centrocymmetric dimers. O—H···O and two C—H···O hydrogenbonds generate spirocyclic R22(8)R21(5) ring motifs (Etter, 1990) these motifs are connected by C(6) chains and C—H···π interactions (Fig. 2 and 3).