The crystal structure of the title compound, C
16H
13NO
3, 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.
Supporting information
CCDC reference: 621493
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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(3
H)-one
top
Crystal data top
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) Å3 | 0.23 × 0.19 × 0.14 mm |
Z = 2 | |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.071 | w = 1/[σ2(Fo2) + (0.0394P)2 + 0.0165P] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.040 (6) |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.87 (3) | 2.09 (3) | 2.959 (3) | 172 (3) |
C6—H6···O3ii | 0.93 | 2.45 | 3.351 (3) | 164 |
C8—H8···O2iii | 0.98 | 2.58 | 3.493 (3) | 155 |
C16—H16B···O1iv | 0.96 | 2.57 | 3.457 (4) | 154 |
C8—H8···Cg1iii | 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. |