The crystal structure of the title compound, C
15H
13NO
2, is stabilized by inversion-related N—H
O and C—H
O intermolecular hydrogen bonds and also by C—H
π interactions. The N—H
O and C—H
O hydrogen bonds generate
C(7) chains and
R22(6)
R44(20)
R22(6) ring motifs. These motifs are linked to each other by C—H
π interactions, generating a three-dimensional network. The phthalide group is planar and makes a dihedral angle of 69.96 (2)° with the
p-tolyl ring.
Supporting information
CCDC reference: 642901
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.002 Å
- R factor = 0.039
- wR factor = 0.103
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level C
CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that
calculated from the cell parameter s.u.'s by > 2
Calculated cell volume su = 15.04
Cell volume su given = 13.00
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.68 mm
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. O2 .. 2.66 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 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-methyanilino)isobenzofuran-1(3
H)-one
top
Crystal data top
C15H13NO2 | F(000) = 504 |
Mr = 239.26 | Dx = 1.314 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 18611 reflections |
a = 13.2510 (9) Å | θ = 2.6–28.0° |
b = 6.8217 (3) Å | µ = 0.09 mm−1 |
c = 16.0257 (12) Å | T = 296 K |
β = 123.391 (5)° | Prism, colourless |
V = 1209.51 (13) Å3 | 0.68 × 0.50 × 0.41 mm |
Z = 4 | |
Data collection top
STOE IPDS 2 diffractometer | 2380 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1905 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.091 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.6° |
ω scans | h = −16→16 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −8→8 |
Tmin = 0.946, Tmax = 0.972 | l = −19→19 |
18611 measured reflections | |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0476P)2 + 0.0922P] where P = (Fo2 + 2Fc2)/3 |
2380 reflections | (Δ/σ)max < 0.001 |
167 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.15 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 | Uiso*/Ueq | Occ. (<1) |
C1 | 0.53371 (12) | 0.25761 (17) | 0.52760 (11) | 0.0567 (3) | |
C2 | 0.50631 (12) | 0.23118 (16) | 0.60387 (10) | 0.0537 (3) | |
C3 | 0.58285 (13) | 0.2042 (2) | 0.70599 (11) | 0.0655 (4) | |
H3 | 0.6662 | 0.1977 | 0.7367 | 0.079* | |
C4 | 0.53177 (15) | 0.1874 (2) | 0.76037 (11) | 0.0711 (4) | |
H4 | 0.5812 | 0.1720 | 0.8293 | 0.085* | |
C5 | 0.40803 (15) | 0.1931 (2) | 0.71420 (11) | 0.0684 (4) | |
H5 | 0.3755 | 0.1807 | 0.7526 | 0.082* | |
C6 | 0.33150 (13) | 0.21678 (19) | 0.61215 (11) | 0.0603 (3) | |
H6 | 0.2481 | 0.2187 | 0.5812 | 0.072* | |
C7 | 0.38262 (12) | 0.23745 (17) | 0.55765 (10) | 0.0523 (3) | |
C8 | 0.32392 (12) | 0.27281 (19) | 0.44823 (10) | 0.0545 (3) | |
H8 | 0.2835 | 0.4006 | 0.4308 | 0.065* | |
C9 | 0.15610 (11) | 0.15168 (19) | 0.28462 (9) | 0.0540 (3) | |
C10 | 0.08236 (12) | −0.0063 (2) | 0.23152 (10) | 0.0629 (4) | |
H10 | 0.0959 | −0.1270 | 0.2630 | 0.075* | |
C11 | −0.01047 (13) | 0.0136 (2) | 0.13296 (11) | 0.0691 (4) | |
H11 | −0.0588 | −0.0945 | 0.0992 | 0.083* | |
C12 | −0.03434 (13) | 0.1891 (2) | 0.08241 (10) | 0.0656 (4) | |
C13 | 0.04218 (13) | 0.3430 (2) | 0.13460 (11) | 0.0692 (4) | |
H13 | 0.0297 | 0.4623 | 0.1022 | 0.083* | |
C14 | 0.13715 (13) | 0.3263 (2) | 0.23379 (11) | 0.0646 (4) | |
H14 | 0.1882 | 0.4325 | 0.2663 | 0.077* | |
C15 | −0.14186 (15) | 0.2118 (3) | −0.02370 (12) | 0.0859 (5) | |
H15A | −0.1837 | 0.0889 | −0.0470 | 0.129* | 0.50 |
H15B | −0.1147 | 0.2515 | −0.0657 | 0.129* | 0.50 |
H15C | −0.1955 | 0.3094 | −0.0259 | 0.129* | 0.50 |
H15D | −0.1456 | 0.3443 | −0.0454 | 0.129* | 0.50 |
H15E | −0.2146 | 0.1817 | −0.0267 | 0.129* | 0.50 |
H15F | −0.1338 | 0.1238 | −0.0665 | 0.129* | 0.50 |
N1 | 0.24036 (10) | 0.12893 (18) | 0.38732 (8) | 0.0604 (3) | |
O1 | 0.63065 (9) | 0.25959 (14) | 0.53687 (9) | 0.0719 (3) | |
O2 | 0.42944 (9) | 0.28242 (14) | 0.43806 (7) | 0.0623 (3) | |
H1 | 0.2617 (14) | 0.009 (2) | 0.4090 (12) | 0.075 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0553 (8) | 0.0450 (6) | 0.0698 (9) | 0.0000 (5) | 0.0345 (7) | 0.0014 (5) |
C2 | 0.0519 (7) | 0.0447 (6) | 0.0579 (7) | −0.0004 (5) | 0.0261 (6) | 0.0010 (5) |
C3 | 0.0560 (8) | 0.0590 (8) | 0.0626 (8) | −0.0003 (6) | 0.0207 (7) | 0.0040 (6) |
C4 | 0.0794 (10) | 0.0645 (8) | 0.0524 (8) | −0.0001 (7) | 0.0255 (7) | 0.0059 (6) |
C5 | 0.0844 (10) | 0.0640 (8) | 0.0631 (9) | −0.0029 (7) | 0.0447 (8) | 0.0023 (6) |
C6 | 0.0597 (8) | 0.0596 (8) | 0.0634 (8) | −0.0020 (6) | 0.0350 (7) | 0.0002 (6) |
C7 | 0.0528 (7) | 0.0468 (6) | 0.0530 (7) | −0.0011 (5) | 0.0265 (6) | 0.0000 (5) |
C8 | 0.0511 (7) | 0.0548 (7) | 0.0552 (7) | −0.0001 (5) | 0.0278 (6) | 0.0007 (5) |
C9 | 0.0461 (6) | 0.0633 (8) | 0.0526 (7) | 0.0004 (5) | 0.0271 (6) | 0.0000 (5) |
C10 | 0.0603 (8) | 0.0647 (8) | 0.0611 (8) | −0.0045 (6) | 0.0318 (7) | −0.0012 (6) |
C11 | 0.0584 (8) | 0.0823 (10) | 0.0611 (8) | −0.0112 (7) | 0.0295 (7) | −0.0099 (7) |
C12 | 0.0514 (7) | 0.0928 (10) | 0.0534 (7) | 0.0013 (7) | 0.0294 (6) | 0.0002 (7) |
C13 | 0.0636 (8) | 0.0800 (10) | 0.0613 (9) | 0.0032 (7) | 0.0327 (7) | 0.0129 (7) |
C14 | 0.0588 (8) | 0.0670 (8) | 0.0621 (8) | −0.0061 (6) | 0.0296 (7) | 0.0029 (6) |
C15 | 0.0625 (9) | 0.1238 (15) | 0.0584 (9) | 0.0033 (9) | 0.0250 (8) | 0.0039 (9) |
N1 | 0.0591 (6) | 0.0531 (7) | 0.0547 (6) | −0.0025 (5) | 0.0223 (5) | 0.0016 (5) |
O1 | 0.0621 (6) | 0.0623 (6) | 0.1010 (8) | 0.0023 (4) | 0.0510 (6) | 0.0060 (5) |
O2 | 0.0608 (6) | 0.0694 (6) | 0.0602 (6) | −0.0014 (4) | 0.0355 (5) | 0.0022 (4) |
Geometric parameters (Å, º) top
C1—O1 | 1.2093 (16) | C9—C10 | 1.3873 (18) |
C1—O2 | 1.3470 (17) | C9—N1 | 1.3990 (17) |
C1—C2 | 1.465 (2) | C10—C11 | 1.374 (2) |
C2—C7 | 1.3786 (19) | C10—H10 | 0.9300 |
C2—C3 | 1.383 (2) | C11—C12 | 1.381 (2) |
C3—C4 | 1.371 (2) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—C13 | 1.377 (2) |
C4—C5 | 1.379 (2) | C12—C15 | 1.510 (2) |
C4—H4 | 0.9300 | C13—C14 | 1.3862 (19) |
C5—C6 | 1.380 (2) | C13—H13 | 0.9300 |
C5—H5 | 0.9300 | C14—H14 | 0.9300 |
C6—C7 | 1.376 (2) | C15—H15A | 0.9600 |
C6—H6 | 0.9300 | C15—H15B | 0.9600 |
C7—C8 | 1.4955 (19) | C15—H15C | 0.9600 |
C8—N1 | 1.3973 (17) | C15—H15D | 0.9600 |
C8—O2 | 1.4957 (17) | C15—H15E | 0.9600 |
C8—H8 | 0.9800 | C15—H15F | 0.9600 |
C9—C14 | 1.3860 (19) | N1—H1 | 0.870 (16) |
| | | |
O1—C1—O2 | 121.80 (13) | C12—C11—H11 | 119.0 |
O1—C1—C2 | 129.27 (13) | C13—C12—C11 | 116.76 (13) |
O2—C1—C2 | 108.93 (11) | C13—C12—C15 | 121.93 (15) |
C7—C2—C3 | 121.37 (13) | C11—C12—C15 | 121.28 (15) |
C7—C2—C1 | 108.37 (12) | C12—C13—C14 | 122.28 (14) |
C3—C2—C1 | 130.26 (13) | C12—C13—H13 | 118.9 |
C4—C3—C2 | 117.78 (14) | C14—C13—H13 | 118.9 |
C4—C3—H3 | 121.1 | C9—C14—C13 | 120.07 (13) |
C2—C3—H3 | 121.1 | C9—C14—H14 | 120.0 |
C3—C4—C5 | 120.90 (14) | C13—C14—H14 | 120.0 |
C3—C4—H4 | 119.5 | C12—C15—H15A | 109.5 |
C5—C4—H4 | 119.5 | C12—C15—H15B | 109.5 |
C4—C5—C6 | 121.37 (14) | H15A—C15—H15B | 109.5 |
C4—C5—H5 | 119.3 | C12—C15—H15C | 109.5 |
C6—C5—H5 | 119.3 | H15A—C15—H15C | 109.5 |
C7—C6—C5 | 117.84 (13) | H15B—C15—H15C | 109.5 |
C7—C6—H6 | 121.1 | C12—C15—H15D | 109.5 |
C5—C6—H6 | 121.1 | H15A—C15—H15D | 141.1 |
C6—C7—C2 | 120.72 (13) | H15B—C15—H15D | 56.3 |
C6—C7—C8 | 129.85 (12) | H15C—C15—H15D | 56.3 |
C2—C7—C8 | 109.41 (12) | C12—C15—H15E | 109.5 |
N1—C8—C7 | 113.99 (11) | H15A—C15—H15E | 56.3 |
N1—C8—O2 | 112.56 (11) | H15B—C15—H15E | 141.1 |
C7—C8—O2 | 102.75 (10) | H15C—C15—H15E | 56.3 |
N1—C8—H8 | 109.1 | H15D—C15—H15E | 109.5 |
C7—C8—H8 | 109.1 | C12—C15—H15F | 109.5 |
O2—C8—H8 | 109.1 | H15A—C15—H15F | 56.3 |
C14—C9—C10 | 117.94 (13) | H15B—C15—H15F | 56.3 |
C14—C9—N1 | 123.78 (12) | H15C—C15—H15F | 141.1 |
C10—C9—N1 | 118.17 (12) | H15D—C15—H15F | 109.5 |
C11—C10—C9 | 120.75 (13) | H15E—C15—H15F | 109.5 |
C11—C10—H10 | 119.6 | C8—N1—C9 | 123.81 (12) |
C9—C10—H10 | 119.6 | C8—N1—H1 | 114.9 (10) |
C10—C11—C12 | 122.07 (14) | C9—N1—H1 | 116.6 (10) |
C10—C11—H11 | 119.0 | C1—O2—C8 | 110.53 (10) |
| | | |
O1—C1—C2—C7 | −179.27 (13) | C14—C9—C10—C11 | −3.3 (2) |
O2—C1—C2—C7 | 0.99 (13) | N1—C9—C10—C11 | 173.03 (13) |
O1—C1—C2—C3 | 0.9 (2) | C9—C10—C11—C12 | 0.3 (2) |
O2—C1—C2—C3 | −178.81 (12) | C10—C11—C12—C13 | 2.1 (2) |
C7—C2—C3—C4 | −1.19 (19) | C10—C11—C12—C15 | −175.77 (14) |
C1—C2—C3—C4 | 178.59 (13) | C11—C12—C13—C14 | −1.5 (2) |
C2—C3—C4—C5 | 1.4 (2) | C15—C12—C13—C14 | 176.36 (15) |
C3—C4—C5—C6 | −0.3 (2) | C10—C9—C14—C13 | 3.9 (2) |
C4—C5—C6—C7 | −0.9 (2) | N1—C9—C14—C13 | −172.24 (13) |
C5—C6—C7—C2 | 1.09 (19) | C12—C13—C14—C9 | −1.5 (2) |
C5—C6—C7—C8 | −177.32 (13) | C7—C8—N1—C9 | 165.36 (12) |
C3—C2—C7—C6 | −0.04 (19) | O2—C8—N1—C9 | −78.12 (15) |
C1—C2—C7—C6 | −179.87 (11) | C14—C9—N1—C8 | −7.3 (2) |
C3—C2—C7—C8 | 178.66 (11) | C10—C9—N1—C8 | 176.59 (12) |
C1—C2—C7—C8 | −1.17 (14) | O1—C1—O2—C8 | 179.84 (11) |
C6—C7—C8—N1 | −58.47 (18) | C2—C1—O2—C8 | −0.40 (13) |
C2—C7—C8—N1 | 122.98 (12) | N1—C8—O2—C1 | −123.33 (12) |
C6—C7—C8—O2 | 179.44 (12) | C7—C8—O2—C1 | −0.28 (12) |
C2—C7—C8—O2 | 0.90 (13) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.870 (16) | 2.189 (17) | 3.0226 (16) | 160.2 (15) |
C5—H5···O2ii | 0.93 | 2.66 | 3.4436 (18) | 143 |
C8—H8···O1iii | 0.98 | 2.51 | 3.2306 (16) | 131 |
C10—H10···Cg1iv | 0.93 | 3.01 | 3.466 | 127 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y+1, −z+1; (iv) −x, y−1/2, −z+1/2. |