In the title compound, C
18H
16N
2O
2, the dihedral angle between the indole ring system and the benzoyl benzene ring is 31.5 (1)°. In the crystalline state, symmetry-related molecules are linked
via N—H
O and C—H
O hydrogen bonds, and π–π interactions to form a layer structure parallel to the
bc plane.
Supporting information
CCDC reference: 287743
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.077
- wR factor = 0.216
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT601_ALERT_2_A Structure Contains Solvent Accessible VOIDS of . 374.00 A 3
| Author Response: Please refer _publ_section_exptl_refinement.
|
Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C16
1 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
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
1 ALERT type 4 Improvement, methodology, query or suggestion
A solution of 1-phenylsulfonyl-2-(2-acetamido-5-methylbenzoyl)indole (5 mmol) in methanol (100 mmol) was refluxed with 10% sodium hydroxide solution (10 ml) for 30 min. The solution was poured over ice and the precipitated solid was filtered off, washed with water, dried over anhydrous calcium chloride and purified by crystallization. Single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a methanol solution.
H atoms were positioned geometrically and treated as riding on their parent atoms, with an N—H distance of 0.86 Å, C—H distances of 0.93 (aromatic) and 0.96 Å (methyl), and with Uiso(H) = 1.5Ueq(methyl C) and 1.2Ueq(other atoms). A rotating group model was used for the methyl groups. The refinement converged to an R value of 0.095 (wR = 0.248) and the difference map showed three highest peaks of 0.81, 0.51 and 0.48 e Å−3. Refinement based on a disordered solvent model led to unstable refinement with very high displacement parameters. A search for solvent-accessible voids in the crystal structure using PLATON (Spek, 2003) showed a potential solvent volume of 746.1 Å3 and subsequent application of SQUEEZE procedures (Sluis & Spek, 1990) showed only one relevant void with a solvent-accessible volume of 373 Å3. However, this procedure showed no electrons in the void as the weak positive and negative density excursions in the void region sum close to zero. This indicates that the crystal lost nearly all of its solvent of crystallization by the time it was used for data collection, without collapse of the structure. Further refinement of the structure with data obtained from the above procedure converged to an R value of 0.077 (wR = 0.216). The limited improvement of R values indicates that there are still residual problems associated with the data. As no more crystals were available, we were unable to repeat the experiment at a lower temperature, on a crystal freshly chosen from the mother liquor.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
2-(2-Acetamido-5-methylbenzoyl)indole
top
Crystal data top
C18H16N2O2 | F(000) = 1232 |
Mr = 292.33 | Dx = 1.098 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2509 reflections |
a = 21.8765 (12) Å | θ = 2.3–28.3° |
b = 14.3774 (8) Å | µ = 0.07 mm−1 |
c = 11.7603 (7) Å | T = 293 K |
β = 107.050 (1)° | Block, colourless |
V = 3536.4 (3) Å3 | 0.36 × 0.20 × 0.10 mm |
Z = 8 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 2067 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.041 |
Graphite monochromator | θmax = 25.0°, θmin = 2.3° |
Detector resolution: 8.33 pixels mm-1 | h = −26→26 |
ω scans | k = −17→9 |
8691 measured reflections | l = −13→13 |
3108 independent 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)] = 0.077 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.216 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.1234P)2 + 0.2753P] where P = (Fo2 + 2Fc2)/3 |
3108 reflections | (Δ/σ)max = 0.001 |
201 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
Crystal data top
C18H16N2O2 | V = 3536.4 (3) Å3 |
Mr = 292.33 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 21.8765 (12) Å | µ = 0.07 mm−1 |
b = 14.3774 (8) Å | T = 293 K |
c = 11.7603 (7) Å | 0.36 × 0.20 × 0.10 mm |
β = 107.050 (1)° | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 2067 reflections with I > 2σ(I) |
8691 measured reflections | Rint = 0.041 |
3108 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.077 | 0 restraints |
wR(F2) = 0.216 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.27 e Å−3 |
3108 reflections | Δρmin = −0.25 e Å−3 |
201 parameters | |
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 | |
O1 | 0.24259 (12) | −0.00154 (16) | 0.3462 (2) | 0.0524 (7) | |
O2 | 0.34245 (13) | 0.28941 (17) | 0.2779 (2) | 0.0543 (7) | |
N1 | 0.14819 (12) | −0.08089 (17) | 0.4111 (2) | 0.0356 (7) | |
H1N | 0.1565 | −0.1067 | 0.3514 | 0.043* | |
N2 | 0.30328 (13) | 0.15428 (19) | 0.3295 (2) | 0.0422 (7) | |
H2N | 0.2858 | 0.1028 | 0.2995 | 0.051* | |
C1 | 0.18169 (14) | −0.0079 (2) | 0.4763 (2) | 0.0304 (7) | |
C2 | 0.15435 (15) | 0.0146 (2) | 0.5644 (3) | 0.0346 (8) | |
H2 | 0.1674 | 0.0619 | 0.6203 | 0.042* | |
C3 | 0.10267 (15) | −0.0478 (2) | 0.5542 (3) | 0.0356 (8) | |
C4 | 0.05740 (17) | −0.0600 (3) | 0.6168 (3) | 0.0506 (10) | |
H4 | 0.0581 | −0.0225 | 0.6817 | 0.061* | |
C5 | 0.01238 (17) | −0.1282 (3) | 0.5803 (4) | 0.0607 (11) | |
H5 | −0.0174 | −0.1374 | 0.6216 | 0.073* | |
C6 | 0.01010 (17) | −0.1845 (3) | 0.4820 (4) | 0.0596 (11) | |
H6 | −0.0215 | −0.2297 | 0.4591 | 0.072* | |
C7 | 0.05319 (16) | −0.1745 (3) | 0.4189 (3) | 0.0477 (9) | |
H7 | 0.0515 | −0.2120 | 0.3536 | 0.057* | |
C8 | 0.09963 (14) | −0.1060 (2) | 0.4564 (3) | 0.0354 (8) | |
C9 | 0.23494 (15) | 0.0302 (2) | 0.4387 (3) | 0.0337 (7) | |
C10 | 0.27804 (14) | 0.1041 (2) | 0.5082 (3) | 0.0309 (7) | |
C11 | 0.28902 (15) | 0.1123 (2) | 0.6301 (3) | 0.0375 (8) | |
H11 | 0.2698 | 0.0696 | 0.6682 | 0.045* | |
C12 | 0.32714 (15) | 0.1807 (2) | 0.6976 (3) | 0.0397 (8) | |
C13 | 0.35524 (16) | 0.2434 (3) | 0.6376 (3) | 0.0455 (9) | |
H13 | 0.3802 | 0.2916 | 0.6798 | 0.055* | |
C14 | 0.34708 (16) | 0.2359 (2) | 0.5181 (3) | 0.0404 (8) | |
H14 | 0.3668 | 0.2787 | 0.4810 | 0.049* | |
C15 | 0.31024 (14) | 0.1661 (2) | 0.4515 (3) | 0.0328 (7) | |
C16 | 0.3385 (2) | 0.1880 (3) | 0.8305 (3) | 0.0684 (13) | |
H16A | 0.3153 | 0.1397 | 0.8562 | 0.103* | |
H16B | 0.3240 | 0.2476 | 0.8492 | 0.103* | |
H16C | 0.3833 | 0.1815 | 0.8705 | 0.103* | |
C17 | 0.31985 (16) | 0.2116 (2) | 0.2520 (3) | 0.0401 (8) | |
C18 | 0.3090 (2) | 0.1711 (3) | 0.1300 (3) | 0.0627 (12) | |
H18A | 0.3190 | 0.2168 | 0.0787 | 0.094* | |
H18B | 0.2650 | 0.1529 | 0.0987 | 0.094* | |
H18C | 0.3359 | 0.1176 | 0.1347 | 0.094* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0813 (18) | 0.0481 (16) | 0.0425 (14) | −0.0239 (13) | 0.0408 (13) | −0.0165 (11) |
O2 | 0.0867 (19) | 0.0450 (16) | 0.0373 (14) | −0.0184 (14) | 0.0277 (13) | −0.0002 (11) |
N1 | 0.0461 (16) | 0.0346 (16) | 0.0305 (14) | −0.0059 (12) | 0.0178 (12) | −0.0061 (12) |
N2 | 0.0648 (19) | 0.0363 (16) | 0.0317 (14) | −0.0183 (14) | 0.0238 (13) | −0.0048 (12) |
C1 | 0.0393 (17) | 0.0247 (17) | 0.0273 (16) | −0.0015 (13) | 0.0101 (14) | −0.0024 (12) |
C2 | 0.0430 (18) | 0.0300 (17) | 0.0325 (17) | −0.0028 (14) | 0.0135 (14) | −0.0060 (13) |
C3 | 0.0386 (18) | 0.0382 (19) | 0.0303 (16) | 0.0066 (14) | 0.0104 (13) | 0.0040 (14) |
C4 | 0.049 (2) | 0.064 (3) | 0.044 (2) | 0.0033 (19) | 0.0221 (17) | 0.0002 (18) |
C5 | 0.041 (2) | 0.078 (3) | 0.069 (3) | −0.006 (2) | 0.0249 (19) | 0.012 (2) |
C6 | 0.040 (2) | 0.065 (3) | 0.073 (3) | −0.0169 (19) | 0.014 (2) | −0.001 (2) |
C7 | 0.042 (2) | 0.047 (2) | 0.049 (2) | −0.0044 (17) | 0.0066 (16) | −0.0042 (17) |
C8 | 0.0362 (17) | 0.0360 (18) | 0.0311 (17) | −0.0026 (14) | 0.0053 (13) | 0.0025 (14) |
C9 | 0.0476 (19) | 0.0300 (18) | 0.0261 (16) | −0.0022 (14) | 0.0147 (14) | 0.0023 (13) |
C10 | 0.0377 (17) | 0.0290 (17) | 0.0290 (16) | 0.0020 (13) | 0.0147 (13) | 0.0043 (13) |
C11 | 0.0432 (19) | 0.044 (2) | 0.0273 (16) | −0.0054 (15) | 0.0131 (14) | 0.0043 (14) |
C12 | 0.0416 (18) | 0.053 (2) | 0.0237 (16) | −0.0070 (16) | 0.0088 (14) | −0.0012 (15) |
C13 | 0.049 (2) | 0.049 (2) | 0.0385 (19) | −0.0163 (17) | 0.0123 (16) | −0.0106 (16) |
C14 | 0.047 (2) | 0.043 (2) | 0.0328 (18) | −0.0119 (16) | 0.0153 (15) | 0.0021 (15) |
C15 | 0.0394 (17) | 0.0320 (18) | 0.0299 (16) | 0.0012 (14) | 0.0144 (14) | 0.0025 (14) |
C16 | 0.077 (3) | 0.095 (3) | 0.032 (2) | −0.031 (2) | 0.0137 (19) | −0.012 (2) |
C17 | 0.050 (2) | 0.044 (2) | 0.0316 (18) | −0.0096 (17) | 0.0192 (15) | 0.0022 (15) |
C18 | 0.098 (3) | 0.061 (3) | 0.038 (2) | −0.026 (2) | 0.034 (2) | −0.0088 (18) |
Geometric parameters (Å, º) top
O1—C9 | 1.235 (3) | C7—C8 | 1.391 (4) |
O2—C17 | 1.225 (4) | C7—H7 | 0.93 |
N1—C8 | 1.369 (4) | C9—C10 | 1.495 (4) |
N1—C1 | 1.377 (4) | C10—C11 | 1.387 (4) |
N1—H1N | 0.86 | C10—C15 | 1.418 (4) |
N2—C17 | 1.355 (4) | C11—C12 | 1.380 (4) |
N2—C15 | 1.408 (4) | C11—H11 | 0.93 |
N2—H2N | 0.86 | C12—C13 | 1.394 (4) |
C1—C2 | 1.379 (4) | C12—C16 | 1.513 (4) |
C1—C9 | 1.468 (4) | C13—C14 | 1.367 (4) |
C2—C3 | 1.420 (4) | C13—H13 | 0.93 |
C2—H2 | 0.93 | C14—C15 | 1.379 (4) |
C3—C8 | 1.408 (4) | C14—H14 | 0.93 |
C3—C4 | 1.408 (5) | C16—H16A | 0.96 |
C4—C5 | 1.367 (5) | C16—H16B | 0.96 |
C4—H4 | 0.93 | C16—H16C | 0.96 |
C5—C6 | 1.399 (5) | C17—C18 | 1.501 (4) |
C5—H5 | 0.93 | C18—H18A | 0.96 |
C6—C7 | 1.368 (5) | C18—H18B | 0.96 |
C6—H6 | 0.93 | C18—H18C | 0.96 |
| | | |
C8—N1—C1 | 109.4 (2) | C11—C10—C15 | 118.2 (3) |
C8—N1—H1N | 125.3 | C11—C10—C9 | 121.1 (3) |
C1—N1—H1N | 125.3 | C15—C10—C9 | 120.7 (3) |
C17—N2—C15 | 129.9 (3) | C12—C11—C10 | 123.2 (3) |
C17—N2—H2N | 115.0 | C12—C11—H11 | 118.4 |
C15—N2—H2N | 115.0 | C10—C11—H11 | 118.4 |
N1—C1—C2 | 108.6 (3) | C11—C12—C13 | 116.8 (3) |
N1—C1—C9 | 117.2 (2) | C11—C12—C16 | 122.2 (3) |
C2—C1—C9 | 134.2 (3) | C13—C12—C16 | 121.0 (3) |
C1—C2—C3 | 107.3 (3) | C14—C13—C12 | 121.7 (3) |
C1—C2—H2 | 126.3 | C14—C13—H13 | 119.2 |
C3—C2—H2 | 126.3 | C12—C13—H13 | 119.2 |
C8—C3—C4 | 118.7 (3) | C13—C14—C15 | 121.3 (3) |
C8—C3—C2 | 106.9 (3) | C13—C14—H14 | 119.3 |
C4—C3—C2 | 134.3 (3) | C15—C14—H14 | 119.3 |
C5—C4—C3 | 118.5 (3) | C14—C15—N2 | 122.5 (3) |
C5—C4—H4 | 120.7 | C14—C15—C10 | 118.6 (3) |
C3—C4—H4 | 120.7 | N2—C15—C10 | 118.9 (3) |
C4—C5—C6 | 121.5 (3) | C12—C16—H16A | 109.5 |
C4—C5—H5 | 119.2 | C12—C16—H16B | 109.5 |
C6—C5—H5 | 119.2 | H16A—C16—H16B | 109.5 |
C7—C6—C5 | 121.6 (3) | C12—C16—H16C | 109.5 |
C7—C6—H6 | 119.2 | H16A—C16—H16C | 109.5 |
C5—C6—H6 | 119.2 | H16B—C16—H16C | 109.5 |
C6—C7—C8 | 117.2 (3) | O2—C17—N2 | 123.8 (3) |
C6—C7—H7 | 121.4 | O2—C17—C18 | 122.1 (3) |
C8—C7—H7 | 121.4 | N2—C17—C18 | 114.1 (3) |
N1—C8—C7 | 129.9 (3) | C17—C18—H18A | 109.5 |
N1—C8—C3 | 107.7 (3) | C17—C18—H18B | 109.5 |
C7—C8—C3 | 122.4 (3) | H18A—C18—H18B | 109.5 |
O1—C9—C1 | 116.9 (3) | C17—C18—H18C | 109.5 |
O1—C9—C10 | 121.2 (3) | H18A—C18—H18C | 109.5 |
C1—C9—C10 | 122.0 (3) | H18B—C18—H18C | 109.5 |
| | | |
C8—N1—C1—C2 | −0.1 (3) | C2—C1—C9—C10 | 7.2 (5) |
C8—N1—C1—C9 | −178.5 (3) | O1—C9—C10—C11 | −152.0 (3) |
N1—C1—C2—C3 | 0.8 (3) | C1—C9—C10—C11 | 28.2 (4) |
C9—C1—C2—C3 | 178.8 (3) | O1—C9—C10—C15 | 26.2 (5) |
C1—C2—C3—C8 | −1.2 (3) | C1—C9—C10—C15 | −153.6 (3) |
C1—C2—C3—C4 | 179.9 (4) | C15—C10—C11—C12 | 3.4 (5) |
C8—C3—C4—C5 | 0.1 (5) | C9—C10—C11—C12 | −178.4 (3) |
C2—C3—C4—C5 | 178.9 (4) | C10—C11—C12—C13 | 0.0 (5) |
C3—C4—C5—C6 | −0.8 (6) | C10—C11—C12—C16 | −179.9 (3) |
C4—C5—C6—C7 | 0.7 (6) | C11—C12—C13—C14 | −2.0 (5) |
C5—C6—C7—C8 | 0.0 (6) | C16—C12—C13—C14 | 177.9 (4) |
C1—N1—C8—C7 | 178.9 (3) | C12—C13—C14—C15 | 0.4 (6) |
C1—N1—C8—C3 | −0.6 (3) | C13—C14—C15—N2 | −177.2 (3) |
C6—C7—C8—N1 | 179.9 (3) | C13—C14—C15—C10 | 3.0 (5) |
C6—C7—C8—C3 | −0.7 (5) | C17—N2—C15—C14 | −11.9 (5) |
C4—C3—C8—N1 | −179.8 (3) | C17—N2—C15—C10 | 167.9 (3) |
C2—C3—C8—N1 | 1.1 (3) | C11—C10—C15—C14 | −4.8 (4) |
C4—C3—C8—C7 | 0.6 (5) | C9—C10—C15—C14 | 176.9 (3) |
C2—C3—C8—C7 | −178.5 (3) | C11—C10—C15—N2 | 175.4 (3) |
N1—C1—C9—O1 | 5.3 (4) | C9—C10—C15—N2 | −2.8 (4) |
C2—C1—C9—O1 | −172.6 (3) | C15—N2—C17—O2 | −3.5 (6) |
N1—C1—C9—C10 | −174.9 (3) | C15—N2—C17—C18 | 175.7 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.86 | 2.14 | 2.954 (3) | 159 |
N2—H2N···O1 | 0.86 | 1.94 | 2.641 (4) | 138 |
C2—H2···O2ii | 0.93 | 2.49 | 3.363 (4) | 156 |
C11—H11···O1iii | 0.93 | 2.53 | 3.397 (4) | 154 |
C14—H14···O2 | 0.93 | 2.29 | 2.901 (4) | 122 |
C16—H16A···O1iii | 0.96 | 2.53 | 3.442 (5) | 160 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1/2, −y+1/2, −z+1; (iii) x, −y, z+1/2. |
Experimental details
Crystal data |
Chemical formula | C18H16N2O2 |
Mr | 292.33 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 21.8765 (12), 14.3774 (8), 11.7603 (7) |
β (°) | 107.050 (1) |
V (Å3) | 3536.4 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.36 × 0.20 × 0.10 |
|
Data collection |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8691, 3108, 2067 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.077, 0.216, 1.09 |
No. of reflections | 3108 |
No. of parameters | 201 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.25 |
Selected geometric parameters (Å, º) topO1—C9 | 1.235 (3) | N2—C17 | 1.355 (4) |
O2—C17 | 1.225 (4) | N2—C15 | 1.408 (4) |
| | | |
C17—N2—C15 | 129.9 (3) | C11—C12—C16 | 122.2 (3) |
O1—C9—C1 | 116.9 (3) | O2—C17—N2 | 123.8 (3) |
C1—C9—C10 | 122.0 (3) | N2—C17—C18 | 114.1 (3) |
C11—C12—C13 | 116.8 (3) | | |
| | | |
C17—N2—C15—C14 | −11.9 (5) | C15—N2—C17—C18 | 175.7 (3) |
C15—N2—C17—O2 | −3.5 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.86 | 2.14 | 2.954 (3) | 159 |
N2—H2N···O1 | 0.86 | 1.94 | 2.641 (4) | 138 |
C2—H2···O2ii | 0.93 | 2.49 | 3.363 (4) | 156 |
C11—H11···O1iii | 0.93 | 2.53 | 3.397 (4) | 154 |
C14—H14···O2 | 0.93 | 2.29 | 2.901 (4) | 122 |
C16—H16A···O1iii | 0.96 | 2.53 | 3.442 (5) | 160 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1/2, −y+1/2, −z+1; (iii) x, −y, z+1/2. |
Many idole derivatives, both natural and synthetic, show important biological activities such as antibacterial, antifungal (Wang & Ng, 2002; Singh et al., 2000; Tsotinis et al., 1997; Quetin-Leclercq et al., 1995), antitumour (Andreani et al., 2001; Bradlow et al., 1999; Cirrincione et al., 1999; Tiwari et al., 1994; Dashwood et al., 1994) and antimicrobial activities (Piscopo, Diurno, Mazzoni & Ciaccio, 1990; Piscopo, Diurno, Mazzoni, Ciaccio & Veneruso, 1990). Some indole derivatives are used as neuroprotectants (Stolc, 1999). Recently, we have reported the crystal structures of some phenylsulfonylindole derivatives (Ravishankar et al., 2003a,b, 2005a,b). We report here the crystal structure of the title compound, (I).
The indole ring system in (I) (Fig. 1) is planar, with a maximum deviation of 0.017 (3) Å for atom C2. The N—Csp2 bond lengths, viz. N1—C1 [1.377 (4) Å] and N1—C8 [1.369 (4) Å], are comparable with the mean value of 1.355 (14) Å reported for N atoms with planar configurations (Allen et al., 1987). These values are significantly longer in phenylsulfonyl indole derivatives (Ravishankar et al., 2003a,b, Ravishankar et al., 2005a,b). The conformation of the attachment of the benzoyl substituent to the indole ring system is described by the C2—C1—C9—C10 torsion angle of 7.2 (5)°; the C1—C9—C10—C11 torsion angle of 28.2 (4)° shows how the C10–C15 ring is oriented. The mean plane through the acetylamide group makes a dihedral angle of 15.1 (2)° with the C10–C15 ring. This orientation is influenced by the intramolecular N2—H2N···O1 and C14—H14···O2 hydrogen bonds involving carbonyl atoms O1 and O2 (Table 1). Each of these interactions generates rings of graph-set motif S(6) (Bernstein et al., 1995; Etter, 1990).
The packing of the molecules, shown in Fig. 2, reveals that symmetry-related molecules are linked via N—H···O and C—H···O hydrogen bonds to form a layer structure parallel to the bc plane. Within a layer, the C10–C15 benzene rings at the symmetry positions (x, y, z) and (1/2 − x, 1/2 − y, 1 − z) are stacked with their centroids 3.688 (2) Å apart, indicating the presence of π–π interactions.