Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812013384/bt5862sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536812013384/bt5862Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536812013384/bt5862Isup3.cml |
CCDC reference: 880125
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.047
- wR factor = 0.143
- Data-to-parameter ratio = 18.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 3
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF .... ? PLAT007_ALERT_5_G Note: Number of Unrefined D-H Atoms ............ 1
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 2 ALERT level G = General information/check it is not something unexpected 0 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 2 ALERT type 5 Informative message, check
To 1H-benzimidazol-2(3H)-one (0,2 g, 1,5 mmol), potassium carbonate (0.41 g, 3 mmol), and tetra-n-butylammonium bromide (0.1 g, 0.3 mmol) in DMF (15 ml) was added 1-bromooctane (0.3 ml, 1.8 mmol). Stirring was continued at room temperature for 6 h. The salt was removed by filtration and the filtrate concentrated under reduced pressure. The residue was separated by chromatography on a column of silica gel with ethyl acetate/hexane (1/2) as eluent. Colorless crystals were isolated when the solvent was allowed to evaporate.
H atoms were located in a difference map and treated as riding with N—H = 0.86 Å, C—H = 0.93 Å (aromatic), C—H = 0.97 Å (methylene) and C—H = 0.96 Å (methyl) with Uiso(H) = 1.2 Ueq (aromatic, methylene) and Uiso(H) = 1.5 Ueq(methyl).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).
C15H22N2O | F(000) = 536 |
Mr = 246.35 | Dx = 1.129 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3020 reflections |
a = 14.8888 (18) Å | θ = 2.4–26.5° |
b = 5.8395 (6) Å | µ = 0.07 mm−1 |
c = 16.6778 (19) Å | T = 296 K |
β = 91.448 (3)° | Needle, colourless |
V = 1449.6 (3) Å3 | 0.54 × 0.43 × 0.12 mm |
Z = 4 |
Bruker X8 APEX diffractometer | 1971 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 26.5°, θmin = 2.4° |
ϕ and ω scans | h = −18→18 |
8760 measured reflections | k = −5→7 |
3020 independent reflections | l = −19→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.143 | w = 1/[σ2(Fo2) + (0.0608P)2 + 0.2949P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3020 reflections | Δρmax = 0.18 e Å−3 |
164 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.010 (2) |
C15H22N2O | V = 1449.6 (3) Å3 |
Mr = 246.35 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.8888 (18) Å | µ = 0.07 mm−1 |
b = 5.8395 (6) Å | T = 296 K |
c = 16.6778 (19) Å | 0.54 × 0.43 × 0.12 mm |
β = 91.448 (3)° |
Bruker X8 APEX diffractometer | 1971 reflections with I > 2σ(I) |
8760 measured reflections | Rint = 0.030 |
3020 independent reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.18 e Å−3 |
3020 reflections | Δρmin = −0.14 e Å−3 |
164 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.94346 (9) | 0.1963 (2) | 0.56368 (7) | 0.0642 (4) | |
N1 | 0.94058 (10) | 0.1858 (2) | 0.42412 (8) | 0.0547 (4) | |
H1 | 0.9690 | 0.0598 | 0.4166 | 0.066* | |
N2 | 0.87525 (9) | 0.4734 (2) | 0.48345 (8) | 0.0517 (4) | |
C2 | 0.90690 (11) | 0.3264 (3) | 0.36345 (10) | 0.0486 (4) | |
C1 | 0.92224 (11) | 0.2755 (3) | 0.49722 (10) | 0.0509 (4) | |
C7 | 0.86541 (11) | 0.5096 (3) | 0.40093 (10) | 0.0499 (4) | |
C3 | 0.90920 (12) | 0.3128 (3) | 0.28082 (10) | 0.0596 (5) | |
H3 | 0.9368 | 0.1908 | 0.2554 | 0.072* | |
C6 | 0.82615 (14) | 0.6843 (3) | 0.35775 (12) | 0.0660 (5) | |
H6 | 0.7991 | 0.8074 | 0.3830 | 0.079* | |
C9 | 0.74157 (14) | 0.6002 (4) | 0.55652 (12) | 0.0696 (6) | |
H9A | 0.7232 | 0.7133 | 0.5954 | 0.084* | |
H9B | 0.7117 | 0.6367 | 0.5058 | 0.084* | |
C4 | 0.86880 (14) | 0.4880 (4) | 0.23756 (11) | 0.0684 (6) | |
H4 | 0.8688 | 0.4832 | 0.1818 | 0.082* | |
C8 | 0.84181 (13) | 0.6198 (3) | 0.54643 (11) | 0.0613 (5) | |
H8A | 0.8565 | 0.7776 | 0.5343 | 0.074* | |
H8B | 0.8721 | 0.5802 | 0.5967 | 0.074* | |
C5 | 0.82845 (15) | 0.6697 (4) | 0.27511 (12) | 0.0721 (6) | |
H5 | 0.8022 | 0.7852 | 0.2441 | 0.087* | |
C10 | 0.71026 (13) | 0.3677 (4) | 0.58346 (13) | 0.0743 (6) | |
H10A | 0.7399 | 0.3306 | 0.6343 | 0.089* | |
H10B | 0.7282 | 0.2540 | 0.5446 | 0.089* | |
C11 | 0.60948 (14) | 0.3539 (4) | 0.59315 (15) | 0.0855 (7) | |
H11A | 0.5922 | 0.4626 | 0.6340 | 0.103* | |
H11B | 0.5800 | 0.3994 | 0.5431 | 0.103* | |
C12 | 0.57598 (15) | 0.1199 (4) | 0.61598 (16) | 0.0896 (7) | |
H12B | 0.6050 | 0.0758 | 0.6663 | 0.107* | |
H12A | 0.5944 | 0.0112 | 0.5756 | 0.107* | |
C13 | 0.47537 (15) | 0.1006 (5) | 0.62485 (16) | 0.0932 (8) | |
H13A | 0.4568 | 0.2077 | 0.6657 | 0.112* | |
H13B | 0.4460 | 0.1449 | 0.5746 | 0.112* | |
C14 | 0.44383 (18) | −0.1364 (6) | 0.64722 (19) | 0.1112 (9) | |
H14A | 0.4632 | −0.2430 | 0.6065 | 0.133* | |
H14B | 0.4734 | −0.1797 | 0.6974 | 0.133* | |
C15 | 0.3454 (2) | −0.1625 (6) | 0.6560 (2) | 0.1342 (12) | |
H15A | 0.3320 | −0.3183 | 0.6697 | 0.201* | |
H15B | 0.3152 | −0.1235 | 0.6064 | 0.201* | |
H15C | 0.3255 | −0.0627 | 0.6977 | 0.201* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0772 (8) | 0.0636 (8) | 0.0520 (8) | 0.0168 (6) | 0.0057 (6) | 0.0123 (6) |
N1 | 0.0628 (9) | 0.0464 (8) | 0.0552 (9) | 0.0099 (7) | 0.0081 (7) | −0.0002 (7) |
N2 | 0.0616 (9) | 0.0464 (8) | 0.0471 (8) | 0.0075 (7) | 0.0023 (6) | 0.0000 (6) |
C2 | 0.0494 (9) | 0.0448 (9) | 0.0518 (9) | −0.0031 (7) | 0.0033 (7) | 0.0014 (8) |
C1 | 0.0515 (9) | 0.0476 (10) | 0.0538 (10) | 0.0006 (8) | 0.0054 (7) | 0.0034 (8) |
C7 | 0.0569 (10) | 0.0452 (9) | 0.0474 (9) | −0.0018 (8) | 0.0001 (7) | 0.0005 (7) |
C3 | 0.0656 (11) | 0.0592 (11) | 0.0543 (11) | −0.0016 (9) | 0.0079 (8) | −0.0064 (9) |
C6 | 0.0856 (14) | 0.0506 (11) | 0.0615 (12) | 0.0135 (10) | −0.0020 (9) | 0.0009 (9) |
C9 | 0.0782 (13) | 0.0693 (13) | 0.0614 (12) | 0.0253 (11) | 0.0050 (9) | −0.0062 (10) |
C4 | 0.0807 (13) | 0.0761 (14) | 0.0483 (10) | −0.0052 (11) | 0.0001 (9) | 0.0033 (10) |
C8 | 0.0783 (13) | 0.0520 (11) | 0.0536 (10) | 0.0100 (9) | 0.0000 (9) | −0.0082 (9) |
C5 | 0.0938 (15) | 0.0654 (13) | 0.0569 (12) | 0.0094 (11) | −0.0057 (10) | 0.0111 (10) |
C10 | 0.0684 (13) | 0.0785 (14) | 0.0764 (14) | 0.0186 (11) | 0.0086 (10) | 0.0031 (11) |
C11 | 0.0713 (14) | 0.0938 (17) | 0.0919 (16) | 0.0211 (12) | 0.0106 (11) | 0.0036 (14) |
C12 | 0.0739 (14) | 0.0947 (18) | 0.1004 (18) | 0.0153 (13) | 0.0087 (12) | −0.0010 (15) |
C13 | 0.0711 (14) | 0.107 (2) | 0.1020 (18) | 0.0144 (14) | 0.0064 (12) | −0.0025 (16) |
C14 | 0.0817 (17) | 0.112 (2) | 0.140 (3) | 0.0135 (16) | 0.0050 (16) | 0.0126 (19) |
C15 | 0.088 (2) | 0.141 (3) | 0.174 (3) | 0.0011 (19) | 0.0011 (19) | 0.013 (2) |
O1—C1 | 1.235 (2) | C8—H8B | 0.9700 |
N1—C1 | 1.361 (2) | C5—H5 | 0.9300 |
N1—C2 | 1.387 (2) | C10—C11 | 1.515 (3) |
N1—H1 | 0.8600 | C10—H10A | 0.9700 |
N2—C1 | 1.367 (2) | C10—H10B | 0.9700 |
N2—C7 | 1.396 (2) | C11—C12 | 1.507 (4) |
N2—C8 | 1.452 (2) | C11—H11A | 0.9700 |
C2—C3 | 1.382 (2) | C11—H11B | 0.9700 |
C2—C7 | 1.391 (2) | C12—C13 | 1.513 (3) |
C7—C6 | 1.371 (2) | C12—H12B | 0.9700 |
C3—C4 | 1.381 (3) | C12—H12A | 0.9700 |
C3—H3 | 0.9300 | C13—C14 | 1.511 (4) |
C6—C5 | 1.382 (3) | C13—H13A | 0.9700 |
C6—H6 | 0.9300 | C13—H13B | 0.9700 |
C9—C10 | 1.507 (3) | C14—C15 | 1.484 (4) |
C9—C8 | 1.511 (3) | C14—H14A | 0.9700 |
C9—H9A | 0.9700 | C14—H14B | 0.9700 |
C9—H9B | 0.9700 | C15—H15A | 0.9600 |
C4—C5 | 1.378 (3) | C15—H15B | 0.9600 |
C4—H4 | 0.9300 | C15—H15C | 0.9600 |
C8—H8A | 0.9700 | ||
C1—N1—C2 | 110.42 (14) | C6—C5—H5 | 119.2 |
C1—N1—H1 | 124.8 | C9—C10—C11 | 113.20 (18) |
C2—N1—H1 | 124.8 | C9—C10—H10A | 108.9 |
C1—N2—C7 | 109.50 (14) | C11—C10—H10A | 108.9 |
C1—N2—C8 | 124.01 (14) | C9—C10—H10B | 108.9 |
C7—N2—C8 | 126.49 (14) | C11—C10—H10B | 108.9 |
C3—C2—N1 | 132.54 (16) | H10A—C10—H10B | 107.8 |
C3—C2—C7 | 120.98 (16) | C12—C11—C10 | 114.20 (18) |
N1—C2—C7 | 106.48 (14) | C12—C11—H11A | 108.7 |
O1—C1—N1 | 127.41 (16) | C10—C11—H11A | 108.7 |
O1—C1—N2 | 125.84 (16) | C12—C11—H11B | 108.7 |
N1—C1—N2 | 106.75 (14) | C10—C11—H11B | 108.7 |
C6—C7—C2 | 121.62 (16) | H11A—C11—H11B | 107.6 |
C6—C7—N2 | 131.52 (16) | C11—C12—C13 | 115.3 (2) |
C2—C7—N2 | 106.85 (14) | C11—C12—H12B | 108.5 |
C4—C3—C2 | 117.20 (17) | C13—C12—H12B | 108.5 |
C4—C3—H3 | 121.4 | C11—C12—H12A | 108.5 |
C2—C3—H3 | 121.4 | C13—C12—H12A | 108.5 |
C7—C6—C5 | 117.19 (18) | H12B—C12—H12A | 107.5 |
C7—C6—H6 | 121.4 | C14—C13—C12 | 114.0 (2) |
C5—C6—H6 | 121.4 | C14—C13—H13A | 108.7 |
C10—C9—C8 | 114.54 (16) | C12—C13—H13A | 108.7 |
C10—C9—H9A | 108.6 | C14—C13—H13B | 108.7 |
C8—C9—H9A | 108.6 | C12—C13—H13B | 108.7 |
C10—C9—H9B | 108.6 | H13A—C13—H13B | 107.6 |
C8—C9—H9B | 108.6 | C15—C14—C13 | 115.6 (2) |
H9A—C9—H9B | 107.6 | C15—C14—H14A | 108.4 |
C5—C4—C3 | 121.48 (18) | C13—C14—H14A | 108.4 |
C5—C4—H4 | 119.3 | C15—C14—H14B | 108.4 |
C3—C4—H4 | 119.3 | C13—C14—H14B | 108.4 |
N2—C8—C9 | 113.18 (15) | H14A—C14—H14B | 107.4 |
N2—C8—H8A | 108.9 | C14—C15—H15A | 109.5 |
C9—C8—H8A | 108.9 | C14—C15—H15B | 109.5 |
N2—C8—H8B | 108.9 | H15A—C15—H15B | 109.5 |
C9—C8—H8B | 108.9 | C14—C15—H15C | 109.5 |
H8A—C8—H8B | 107.8 | H15A—C15—H15C | 109.5 |
C4—C5—C6 | 121.53 (19) | H15B—C15—H15C | 109.5 |
C4—C5—H5 | 119.2 | ||
C1—N1—C2—C3 | 178.89 (18) | N1—C2—C3—C4 | −179.26 (18) |
C1—N1—C2—C7 | −0.48 (18) | C7—C2—C3—C4 | 0.0 (3) |
C2—N1—C1—O1 | −178.99 (16) | C2—C7—C6—C5 | 0.8 (3) |
C2—N1—C1—N2 | 0.88 (18) | N2—C7—C6—C5 | 179.37 (18) |
C7—N2—C1—O1 | 178.93 (16) | C2—C3—C4—C5 | 0.5 (3) |
C8—N2—C1—O1 | −1.0 (3) | C1—N2—C8—C9 | −105.19 (19) |
C7—N2—C1—N1 | −0.95 (18) | C7—N2—C8—C9 | 74.9 (2) |
C8—N2—C1—N1 | 179.15 (15) | C10—C9—C8—N2 | 64.2 (2) |
C3—C2—C7—C6 | −0.7 (3) | C3—C4—C5—C6 | −0.3 (3) |
N1—C2—C7—C6 | 178.77 (17) | C7—C6—C5—C4 | −0.3 (3) |
C3—C2—C7—N2 | −179.57 (15) | C8—C9—C10—C11 | 179.88 (17) |
N1—C2—C7—N2 | −0.11 (17) | C9—C10—C11—C12 | 177.1 (2) |
C1—N2—C7—C6 | −178.07 (19) | C10—C11—C12—C13 | −179.1 (2) |
C8—N2—C7—C6 | 1.8 (3) | C11—C12—C13—C14 | 179.6 (2) |
C1—N2—C7—C2 | 0.66 (18) | C12—C13—C14—C15 | −179.7 (3) |
C8—N2—C7—C2 | −179.44 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.01 | 2.8257 (19) | 159 |
C4—H4···O1ii | 0.93 | 2.52 | 3.312 (2) | 144 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H22N2O |
Mr | 246.35 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 14.8888 (18), 5.8395 (6), 16.6778 (19) |
β (°) | 91.448 (3) |
V (Å3) | 1449.6 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.54 × 0.43 × 0.12 |
Data collection | |
Diffractometer | Bruker X8 APEX diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8760, 3020, 1971 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.143, 1.03 |
No. of reflections | 3020 |
No. of parameters | 164 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.14 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.01 | 2.8257 (19) | 159.2 |
C4—H4···O1ii | 0.93 | 2.52 | 3.312 (2) | 143.8 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x, −y+1/2, z−1/2. |
Benzimidazol-2-one derivatives are useful heterocyclic building blocks and are prominent structural elements of compounds demonstrating a wide variety of pharmacological and biochemical properties (Soderlind et al., 1999).
In this work, we have been able to react 1H-benzimidazol-2(3H)-one with 1-bromooctane in the presence of a catalytic quantity of tetra-n-butylammonium bromide under mild conditions to furnish the title compound (Scheme I).
The 1-octyl-1H-benzimidazol-2(3H)-one molecule structure is built up from fused six-and five-membered rings linked to C8H17 chain as shown in Fig.1. The fused-ring system is essentially planar, with a maximum deviation of 0.0045 (17) Å and 0.0080 (13) Å for C7 and N2 respectively. The dihedral angle between them does not exceed 1.20 (9)°. The octyl group is nearly perpendicular to the benzimidazole plane as indicated by the torsion angle of C1 N2 C8 C9 = -105.19(0.19)°. The structure of the title compound is similar to 1-nonyl-1H-benzimidazol-2(3H)-one (Ouzidan et al., 2011) and 5-chloro-1-nonyl-1H-benzimidazol-2(3H)-one (Kandri Rodi et al., 2011).
In the crystal, the molecules form centrosymmetric dimers linked by N—H···O hydrogen bonds with R22(8) graph set motif.