3-(4-Acetyl­anilino)isobenzofuran-1(3H)-one

The crystal structure of the title compound, C₁₆H₁₃NO₃, is stabilized by an N—H...O and three C—H...O inter­molecular hydrogen bonds and by C—H... π inter­actions. The inter­molecular hydrogen bonds generate R₄⁴(33) and R₄⁴(29) ring motifs. These hydrogen-bonded rings are linked via C(3) chains, generating a three-dimensional framework.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.029
• wR factor = 0.071
• Data-to-parameter ratio = 7.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.95

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.99
           From the CIF: _reflns_number_total               1300
           Count of symmetry unique reflns         1300
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   2 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

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, 1990); 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).

3-(4-acetylanilino)isobenzofuran-1(3H)-one

Crystal data

C16H13NO3	F(000) = 280
Mr = 267.27	Dx = 1.391 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7243 reflections
a = 4.0243 (5) Å	θ = 2.3–28.0°
b = 14.3117 (12) Å	µ = 0.10 mm^−1
c = 11.1107 (12) Å	T = 296 K
β = 94.002 (9)°	Prism, colorless
V = 638.36 (12) Å^3	0.23 × 0.19 × 0.14 mm
Z = 2

Data collection

Stoe IPDS-2 diffractometer	1116 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	Rint = 0.051
Plane graphite monochromator	θmax = 26.0°, θmin = 2.3°
Detector resolution: 6.67 pixels mm^-1	h = −4→4
ω scans	k = −17→17
7243 measured reflections	l = −13→13
1300 independent 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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.071	w = 1/[σ^2(Fo^2) + (0.0394P)^2 + 0.0165P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1300 reflections	Δρmax = 0.11 e Å^−3
187 parameters	Δρmin = −0.12 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.040 (6)

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	0.0661 (6)	0.54006 (19)	0.4995 (2)	0.0516 (5)
C2	0.1653 (6)	0.62294 (16)	0.4347 (2)	0.0457 (5)
C3	0.1251 (7)	0.71654 (18)	0.4620 (2)	0.0582 (7)
H3	0.0300	0.7349	0.5322	0.070*
C4	0.2309 (8)	0.78139 (17)	0.3816 (3)	0.0643 (7)
H4	0.2070	0.8448	0.3972	0.077*
C5	0.3722 (8)	0.7531 (2)	0.2781 (3)	0.0646 (8)
H5	0.4418	0.7983	0.2251	0.078*
C6	0.4137 (7)	0.65984 (16)	0.2504 (2)	0.0522 (6)
H6	0.5097	0.6415	0.1804	0.063*
C7	0.3061 (6)	0.59522 (15)	0.33125 (19)	0.0435 (5)
C8	0.3188 (6)	0.49058 (15)	0.3279 (2)	0.0440 (5)
H8	0.5514	0.4699	0.3364	0.053*
C9	0.2094 (6)	0.35914 (14)	0.1890 (2)	0.0413 (5)
C10	0.0823 (6)	0.32922 (16)	0.07531 (19)	0.0468 (5)
H10	−0.0321	0.3710	0.0234	0.056*
C11	0.1254 (6)	0.23883 (16)	0.0400 (2)	0.0478 (6)
H11	0.0389	0.2198	−0.0359	0.057*
C12	0.2967 (6)	0.17436 (15)	0.1155 (2)	0.0426 (5)
C13	0.4193 (6)	0.20426 (16)	0.2279 (2)	0.0461 (5)
H13	0.5330	0.1622	0.2796	0.055*
C14	0.3771 (6)	0.29514 (15)	0.2653 (2)	0.0468 (6)
H14	0.4610	0.3136	0.3418	0.056*
C15	0.3333 (6)	0.07722 (15)	0.0731 (2)	0.0485 (6)
C16	0.5116 (8)	0.00744 (17)	0.1540 (3)	0.0596 (7)
H16A	0.5506	−0.0484	0.1092	0.071*
H16B	0.3780	−0.0072	0.2197	0.071*
H16C	0.7207	0.0331	0.1851	0.071*
N1	0.1603 (5)	0.45111 (13)	0.22315 (17)	0.0475 (5)
O1	−0.0702 (6)	0.53323 (16)	0.59211 (16)	0.0756 (6)
O2	0.1488 (4)	0.46302 (11)	0.43641 (15)	0.0518 (4)
O3	0.2175 (6)	0.05329 (13)	−0.02658 (16)	0.0686 (5)
H1	0.050 (9)	0.486 (2)	0.170 (3)	0.076 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0551 (14)	0.0572 (13)	0.0422 (12)	−0.0021 (13)	0.0010 (10)	−0.0032 (12)
C2	0.0470 (13)	0.0465 (11)	0.0430 (13)	−0.0010 (10)	−0.0017 (11)	−0.0052 (10)
C3	0.0625 (16)	0.0551 (14)	0.0560 (14)	0.0071 (12)	−0.0024 (12)	−0.0156 (12)
C4	0.081 (2)	0.0378 (13)	0.0722 (18)	0.0018 (12)	−0.0087 (15)	−0.0109 (12)
C5	0.080 (2)	0.0466 (14)	0.0665 (17)	−0.0073 (13)	−0.0028 (15)	0.0073 (13)
C6	0.0604 (16)	0.0487 (13)	0.0475 (13)	−0.0029 (11)	0.0047 (12)	−0.0006 (10)
C7	0.0451 (14)	0.0413 (11)	0.0437 (12)	0.0020 (9)	−0.0006 (10)	−0.0025 (10)
C8	0.0483 (14)	0.0425 (12)	0.0411 (12)	−0.0005 (9)	0.0016 (10)	−0.0017 (9)
C9	0.0476 (12)	0.0371 (11)	0.0391 (11)	−0.0018 (9)	0.0030 (9)	0.0006 (8)
C10	0.0564 (14)	0.0446 (12)	0.0383 (11)	0.0014 (10)	−0.0038 (10)	0.0031 (9)
C11	0.0566 (14)	0.0466 (13)	0.0393 (11)	−0.0065 (10)	−0.0034 (10)	−0.0036 (10)
C12	0.0464 (13)	0.0409 (12)	0.0408 (12)	−0.0046 (9)	0.0054 (10)	−0.0024 (9)
C13	0.0549 (14)	0.0404 (11)	0.0424 (12)	0.0010 (10)	−0.0001 (11)	0.0024 (10)
C14	0.0576 (15)	0.0436 (12)	0.0382 (11)	−0.0001 (10)	−0.0032 (10)	−0.0018 (9)
C15	0.0584 (15)	0.0419 (12)	0.0459 (12)	−0.0096 (10)	0.0087 (11)	−0.0031 (10)
C16	0.0733 (18)	0.0431 (12)	0.0628 (15)	0.0061 (11)	0.0086 (14)	−0.0036 (11)
N1	0.0586 (12)	0.0386 (10)	0.0439 (11)	0.0036 (9)	−0.0056 (9)	−0.0031 (8)
O1	0.0955 (15)	0.0832 (14)	0.0504 (10)	−0.0078 (13)	0.0225 (10)	−0.0032 (11)
O2	0.0644 (10)	0.0469 (9)	0.0440 (9)	−0.0037 (8)	0.0026 (8)	0.0010 (7)
O3	0.1013 (15)	0.0505 (10)	0.0525 (10)	−0.0134 (10)	−0.0052 (9)	−0.0096 (9)

Geometric parameters (Å, º)

C1—O1	1.203 (3)	C9—C14	1.390 (3)
C1—O2	1.360 (3)	C9—C10	1.397 (3)
C1—C2	1.458 (4)	C10—C11	1.366 (3)
C2—C7	1.375 (3)	C10—H10	0.9300
C2—C3	1.386 (3)	C11—C12	1.396 (3)
C3—C4	1.376 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.378 (3)
C4—C5	1.379 (4)	C12—C15	1.479 (3)
C4—H4	0.9300	C13—C14	1.380 (3)
C5—C6	1.383 (4)	C13—H13	0.9300
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.380 (3)	C15—O3	1.220 (3)
C6—H6	0.9300	C15—C16	1.493 (4)
C7—C8	1.499 (3)	C16—H16A	0.9600
C8—N1	1.406 (3)	C16—H16B	0.9600
C8—O2	1.481 (3)	C16—H16C	0.9600
C8—H8	0.9800	N1—H1	0.87 (3)
C9—N1	1.388 (3)
O1—C1—O2	121.2 (3)	C14—C9—C10	118.76 (19)
O1—C1—C2	130.2 (2)	C11—C10—C9	120.3 (2)
O2—C1—C2	108.63 (18)	C11—C10—H10	119.9
C7—C2—C3	121.6 (2)	C9—C10—H10	119.9
C7—C2—C1	108.7 (2)	C10—C11—C12	121.4 (2)
C3—C2—C1	129.7 (2)	C10—C11—H11	119.3
C4—C3—C2	117.6 (2)	C12—C11—H11	119.3
C4—C3—H3	121.2	C13—C12—C11	118.01 (19)
C2—C3—H3	121.2	C13—C12—C15	122.9 (2)
C3—C4—C5	120.5 (2)	C11—C12—C15	119.0 (2)
C3—C4—H4	119.7	C12—C13—C14	121.5 (2)
C5—C4—H4	119.7	C12—C13—H13	119.3
C4—C5—C6	122.2 (3)	C14—C13—H13	119.3
C4—C5—H5	118.9	C13—C14—C9	120.1 (2)
C6—C5—H5	118.9	C13—C14—H14	119.9
C7—C6—C5	117.0 (2)	C9—C14—H14	119.9
C7—C6—H6	121.5	O3—C15—C12	120.9 (2)
C5—C6—H6	121.5	O3—C15—C16	119.7 (2)
C2—C7—C6	121.1 (2)	C12—C15—C16	119.4 (2)
C2—C7—C8	109.0 (2)	C15—C16—H16A	109.5
C6—C7—C8	129.9 (2)	C15—C16—H16B	109.5
N1—C8—O2	110.99 (18)	H16A—C16—H16B	109.5
N1—C8—C7	114.1 (2)	C15—C16—H16C	109.5
O2—C8—C7	103.16 (18)	H16A—C16—H16C	109.5
N1—C8—H8	109.5	H16B—C16—H16C	109.5
O2—C8—H8	109.5	C9—N1—C8	122.82 (19)
C7—C8—H8	109.5	C9—N1—H1	116 (2)
N1—C9—C14	122.06 (19)	C8—N1—H1	121 (2)
N1—C9—C10	119.2 (2)	C1—O2—C8	110.32 (17)
O1—C1—C2—C7	−178.5 (3)	C9—C10—C11—C12	−0.2 (4)
O2—C1—C2—C7	0.5 (3)	C10—C11—C12—C13	0.6 (3)
O1—C1—C2—C3	−0.9 (4)	C10—C11—C12—C15	179.5 (3)
O2—C1—C2—C3	178.2 (2)	C11—C12—C13—C14	−0.3 (3)
C7—C2—C3—C4	0.1 (4)	C15—C12—C13—C14	−179.1 (2)
C1—C2—C3—C4	−177.3 (3)	C12—C13—C14—C9	−0.4 (4)
C2—C3—C4—C5	−0.1 (4)	N1—C9—C14—C13	179.8 (2)
C3—C4—C5—C6	0.0 (5)	C10—C9—C14—C13	0.8 (3)
C4—C5—C6—C7	0.2 (4)	C13—C12—C15—O3	179.1 (2)
C3—C2—C7—C6	0.1 (4)	C11—C12—C15—O3	0.3 (3)
C1—C2—C7—C6	178.0 (2)	C13—C12—C15—C16	−0.3 (4)
C3—C2—C7—C8	179.4 (2)	C11—C12—C15—C16	−179.1 (2)
C1—C2—C7—C8	−2.8 (3)	C14—C9—N1—C8	10.4 (3)
C5—C6—C7—C2	−0.2 (4)	C10—C9—N1—C8	−170.6 (2)
C5—C6—C7—C8	−179.3 (3)	O2—C8—N1—C9	−79.6 (3)
C2—C7—C8—N1	124.2 (2)	C7—C8—N1—C9	164.4 (2)
C6—C7—C8—N1	−56.6 (4)	O1—C1—O2—C8	−178.9 (2)
C2—C7—C8—O2	3.7 (2)	C2—C1—O2—C8	2.0 (2)
C6—C7—C8—O2	−177.1 (2)	N1—C8—O2—C1	−126.0 (2)
N1—C9—C10—C11	−179.5 (2)	C7—C8—O2—C1	−3.5 (2)
C14—C9—C10—C11	−0.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3^i	0.87 (3)	2.09 (3)	2.959 (3)	172 (3)
C6—H6···O3^ii	0.93	2.45	3.351 (3)	164
C8—H8···O2^iii	0.98	2.58	3.493 (3)	155
C16—H16B···O1^iv	0.96	2.57	3.457 (4)	154
C8—H8···Cg1^iii	0.98	2.87	3.671 (3)	140

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