2-Acetyl-3-(benzoyl­amino)-1-benzo­furan

The title compound, C₁₇H₁₃NO₃, displays the characteristic features of benzo­furan derivatives. The mol­ecule is nearly planar. An intramolecular N—H...O hydrogen bond, together with π—π stacking interactions, helps to stabilize the structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.073
• wR factor = 0.195
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         37 Perc.

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.141
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.14
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.80 mm
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C11    -   C12    ...       1.53 Ang.
PLAT414_ALERT_2_C Short Intra D-H..H-X       H1     ..  H17     ..       1.95 Ang.

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

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

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-Acetyl-3-(benzoylamino)-1-benzofuran

Crystal data

C17H13NO3	F(000) = 584
Mr = 279.28	Dx = 1.380 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7057 reflections
a = 8.9283 (12) Å	θ = 2.0–26.9°
b = 7.4852 (12) Å	µ = 0.10 mm^−1
c = 20.273 (3) Å	T = 293 K
β = 97.032 (11)°	Plate, colourless
V = 1344.7 (3) Å^3	0.80 × 0.34 × 0.08 mm
Z = 4

Data collection

Stoe IPDS-2 diffractometer	2615 independent reflections
Radiation source: fine-focus sealed tube	964 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.141
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.0°
ω scans	h = −11→10
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.953, Tmax = 0.994	l = −24→24
7795 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.073	H-atom parameters constrained
wR(F^2) = 0.195	w = 1/[σ^2(Fo^2) + (0.0791P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.84	(Δ/σ)max < 0.001
2615 reflections	Δρmax = 0.21 e Å^−3
191 parameters	Δρmin = −0.29 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.3567 (6)	0.3758 (6)	0.40667 (19)	0.0650 (12)
C2	0.3090 (7)	0.4302 (6)	0.3406 (2)	0.0827 (15)
H2	0.2205	0.4936	0.3282	0.099*
C3	0.4075 (7)	0.3796 (7)	0.2964 (2)	0.0898 (17)
H3	0.3852	0.4132	0.2521	0.108*
C4	0.5338 (7)	0.2843 (7)	0.3141 (2)	0.0860 (16)
H4	0.5925	0.2508	0.2813	0.103*
C5	0.5805 (6)	0.2336 (6)	0.38013 (19)	0.0714 (13)
H5	0.6691	0.1697	0.3920	0.086*
C6	0.4861 (5)	0.2847 (6)	0.42700 (17)	0.0620 (12)
C7	0.4824 (5)	0.2553 (5)	0.49818 (18)	0.0603 (11)
C8	0.3517 (5)	0.3264 (6)	0.51268 (18)	0.0631 (11)
C9	0.2817 (6)	0.3266 (6)	0.5743 (2)	0.0694 (12)
C10	0.1326 (5)	0.4068 (7)	0.5752 (2)	0.0846 (15)
H10A	0.1020	0.3945	0.6187	0.127*
H10B	0.0610	0.3474	0.5433	0.127*
H10C	0.1368	0.5312	0.5640	0.127*
C11	0.7248 (6)	0.1290 (6)	0.5454 (2)	0.0687 (12)
C12	0.8068 (5)	0.0512 (6)	0.60972 (19)	0.0632 (12)
C13	0.9417 (6)	−0.0347 (6)	0.6083 (2)	0.0791 (14)
H13	0.9832	−0.0426	0.5684	0.095*
C14	1.0165 (6)	−0.1089 (8)	0.6647 (3)	0.0934 (16)
H14	1.1101	−0.1626	0.6635	0.112*
C15	0.9529 (6)	−0.1039 (7)	0.7228 (2)	0.0850 (15)
H15	1.0012	−0.1601	0.7604	0.102*
C16	0.8208 (6)	−0.0181 (7)	0.7259 (2)	0.0804 (15)
H16	0.7811	−0.0110	0.7662	0.097*
C17	0.7441 (6)	0.0594 (6)	0.6695 (2)	0.0716 (13)
H17	0.6520	0.1160	0.6714	0.086*
N1	0.5810 (4)	0.1738 (5)	0.54640 (14)	0.0627 (10)
H1	0.5442	0.1480	0.5825	0.075*
O1	0.2679 (3)	0.4062 (4)	0.45681 (12)	0.0698 (9)
O2	0.3532 (4)	0.2526 (4)	0.62297 (13)	0.0832 (11)
O3	0.7954 (4)	0.1508 (5)	0.49755 (14)	0.0961 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.078 (4)	0.065 (3)	0.052 (2)	−0.009 (3)	0.007 (2)	−0.007 (2)
C2	0.109 (4)	0.081 (3)	0.055 (3)	−0.005 (3)	−0.001 (3)	0.004 (2)
C3	0.121 (5)	0.097 (4)	0.050 (3)	−0.010 (4)	0.003 (3)	0.012 (3)
C4	0.111 (5)	0.098 (4)	0.052 (3)	−0.017 (4)	0.021 (3)	0.003 (3)
C5	0.083 (4)	0.075 (3)	0.060 (2)	−0.009 (3)	0.021 (2)	−0.007 (2)
C6	0.071 (3)	0.067 (3)	0.048 (2)	−0.011 (3)	0.009 (2)	−0.005 (2)
C7	0.070 (3)	0.063 (3)	0.048 (2)	0.000 (2)	0.006 (2)	−0.003 (2)
C8	0.069 (3)	0.068 (3)	0.049 (2)	0.005 (3)	−0.004 (2)	−0.003 (2)
C9	0.071 (3)	0.080 (3)	0.057 (3)	0.004 (3)	0.011 (2)	−0.011 (2)
C10	0.073 (4)	0.114 (4)	0.067 (3)	0.001 (3)	0.012 (2)	−0.011 (3)
C11	0.070 (3)	0.074 (3)	0.063 (3)	−0.004 (3)	0.008 (2)	−0.009 (2)
C12	0.065 (3)	0.066 (3)	0.058 (2)	−0.006 (2)	0.006 (2)	−0.002 (2)
C13	0.069 (4)	0.092 (3)	0.080 (3)	0.006 (3)	0.024 (3)	−0.001 (3)
C14	0.070 (4)	0.120 (4)	0.089 (3)	0.016 (3)	0.005 (3)	0.013 (3)
C15	0.076 (4)	0.103 (4)	0.073 (3)	0.008 (3)	−0.005 (3)	0.006 (3)
C16	0.081 (4)	0.105 (4)	0.052 (3)	0.009 (3)	−0.005 (2)	−0.006 (3)
C17	0.072 (3)	0.083 (3)	0.060 (3)	0.010 (3)	0.009 (2)	−0.010 (2)
N1	0.058 (3)	0.081 (3)	0.0488 (18)	0.004 (2)	0.0073 (17)	−0.0008 (17)
O1	0.076 (2)	0.078 (2)	0.0534 (16)	0.0062 (17)	0.0011 (15)	−0.0047 (15)
O2	0.088 (3)	0.111 (3)	0.0501 (15)	0.010 (2)	0.0062 (16)	0.0000 (17)
O3	0.082 (3)	0.144 (3)	0.0655 (19)	0.009 (2)	0.0231 (18)	0.013 (2)

Geometric parameters (Å, º)

C1—C6	1.361 (6)	C10—H10A	0.9600
C1—O1	1.382 (5)	C10—H10B	0.9600
C1—C2	1.415 (6)	C10—H10C	0.9600
C2—C3	1.383 (7)	C11—O3	1.232 (5)
C2—H2	0.9300	C11—N1	1.330 (5)
C3—C4	1.346 (7)	C11—C12	1.530 (6)
C3—H3	0.9300	C12—C13	1.369 (6)
C4—C5	1.405 (6)	C12—C17	1.397 (5)
C4—H4	0.9300	C13—C14	1.370 (6)
C5—C6	1.399 (6)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.368 (7)
C6—C7	1.464 (5)	C14—H14	0.9300
C7—C8	1.347 (6)	C15—C16	1.352 (6)
C7—N1	1.376 (5)	C15—H15	0.9300
C8—O1	1.412 (5)	C16—C17	1.387 (6)
C8—C9	1.464 (6)	C16—H16	0.9300
C9—O2	1.239 (5)	C17—H17	0.9300
C9—C10	1.462 (6)	N1—H1	0.8600
C6—C1—O1	113.7 (4)	H10A—C10—H10B	109.5
C6—C1—C2	125.2 (4)	C9—C10—H10C	109.5
O1—C1—C2	121.0 (5)	H10A—C10—H10C	109.5
C3—C2—C1	113.1 (5)	H10B—C10—H10C	109.5
C3—C2—H2	123.4	O3—C11—N1	124.5 (4)
C1—C2—H2	123.4	O3—C11—C12	119.0 (4)
C4—C3—C2	123.5 (4)	N1—C11—C12	116.5 (4)
C4—C3—H3	118.3	C13—C12—C17	119.1 (4)
C2—C3—H3	118.3	C13—C12—C11	119.4 (4)
C3—C4—C5	122.6 (5)	C17—C12—C11	121.5 (4)
C3—C4—H4	118.7	C12—C13—C14	120.8 (4)
C5—C4—H4	118.7	C12—C13—H13	119.6
C6—C5—C4	116.1 (5)	C14—C13—H13	119.6
C6—C5—H5	122.0	C15—C14—C13	119.8 (5)
C4—C5—H5	122.0	C15—C14—H14	120.1
C1—C6—C5	119.4 (4)	C13—C14—H14	120.1
C1—C6—C7	104.7 (4)	C16—C15—C14	120.7 (5)
C5—C6—C7	135.8 (5)	C16—C15—H15	119.7
C8—C7—N1	121.1 (3)	C14—C15—H15	119.7
C8—C7—C6	106.3 (4)	C15—C16—C17	120.3 (4)
N1—C7—C6	132.6 (4)	C15—C16—H16	119.8
C7—C8—O1	112.4 (3)	C17—C16—H16	119.8
C7—C8—C9	131.2 (4)	C16—C17—C12	119.2 (4)
O1—C8—C9	116.4 (4)	C16—C17—H17	120.4
O2—C9—C10	123.8 (4)	C12—C17—H17	120.4
O2—C9—C8	116.5 (4)	C11—N1—C7	129.5 (4)
C10—C9—C8	119.7 (4)	C11—N1—H1	115.2
C9—C10—H10A	109.5	C7—N1—H1	115.2
C9—C10—H10B	109.5	C1—O1—C8	103.0 (3)
C6—C1—C2—C3	0.8 (7)	O1—C8—C9—C10	0.1 (6)
O1—C1—C2—C3	−176.3 (4)	O3—C11—C12—C13	−16.9 (6)
C1—C2—C3—C4	1.6 (7)	N1—C11—C12—C13	165.2 (4)
C2—C3—C4—C5	−2.7 (8)	O3—C11—C12—C17	165.8 (5)
C3—C4—C5—C6	1.3 (7)	N1—C11—C12—C17	−12.2 (6)
O1—C1—C6—C5	175.3 (4)	C17—C12—C13—C14	−1.3 (7)
C2—C1—C6—C5	−2.0 (7)	C11—C12—C13—C14	−178.7 (4)
O1—C1—C6—C7	−1.0 (5)	C12—C13—C14—C15	2.7 (8)
C2—C1—C6—C7	−178.3 (4)	C13—C14—C15—C16	−3.5 (8)
C4—C5—C6—C1	1.0 (6)	C14—C15—C16—C17	2.9 (8)
C4—C5—C6—C7	175.8 (5)	C15—C16—C17—C12	−1.5 (7)
C1—C6—C7—C8	1.5 (5)	C13—C12—C17—C16	0.7 (7)
C5—C6—C7—C8	−173.9 (5)	C11—C12—C17—C16	178.0 (4)
C1—C6—C7—N1	−179.1 (4)	O3—C11—N1—C7	−2.1 (8)
C5—C6—C7—N1	5.6 (8)	C12—C11—N1—C7	175.8 (4)
N1—C7—C8—O1	179.0 (3)	C8—C7—N1—C11	−165.0 (5)
C6—C7—C8—O1	−1.5 (5)	C6—C7—N1—C11	15.6 (8)
N1—C7—C8—C9	−4.3 (8)	C6—C1—O1—C8	0.2 (5)
C6—C7—C8—C9	175.2 (5)	C2—C1—O1—C8	177.6 (4)
C7—C8—C9—O2	1.6 (8)	C7—C8—O1—C1	0.9 (5)
O1—C8—C9—O2	178.2 (4)	C9—C8—O1—C1	−176.4 (4)
C7—C8—C9—C10	−176.6 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	2.13	2.768 (5)	131