


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807065427/xu2381sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807065427/xu2381Isup2.hkl |
CCDC reference: 677864
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.039
- wR factor = 0.101
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2 ... ?
Alert level G PLAT793_ALERT_2_G Check 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 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
To a solution of DMF (10 ml) and ZnCl2 (6 mmol) were added substituted 2-aminobenzonitrile (6 mmol) and acetophenone (6 mmol). The mixture was heated at reflux for 3 h. After completion of the reaction as indicated by TLC (eluent: ethyl acetate), the cooled reaction mixture was quenched with water and the precipitate was separated by filtration. The filtration residue was dispersed into water and titrated to pH 12–13 by 20% sodium hydroxide. After filtration, the product was isolated by column chromatography (200–300 mesh silica gel, ethyl acetate-petroleum with 1:2); yield 62%. Single crystals were obtained from an ethanol solution by slow evaporation at room temperature.
Imino H atoms were located in a difference Fourier map and refined isotropically. Other H atoms were placed inca lucalculated positions with C—H = 0.95 (aromatic) or 0.98 Å (methyl), and refined in riding mode with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) (for methyl group).
Data collection: CrystalClear (Rigaku, 2004); cell refinement: CrystalClear (Rigaku, 2004); data reduction: CrystalClear (Rigaku, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C15H14N2O | F(000) = 504 |
Mr = 238.28 | Dx = 1.319 Mg m−3 |
Monoclinic, P21/n | Melting point = 505–507 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71070 Å |
a = 8.4891 (7) Å | Cell parameters from 3772 reflections |
b = 8.7741 (8) Å | θ = 2.6–27.9° |
c = 16.1351 (16) Å | µ = 0.08 mm−1 |
β = 93.543 (7)° | T = 113 K |
V = 1199.51 (19) Å3 | Prism, colorless |
Z = 4 | 0.28 × 0.24 × 0.22 mm |
Rigaku Saturn diffractometer | 2459 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.034 |
Confocal monochromator | θmax = 27.9°, θmin = 2.6° |
Detector resolution: 7.31 pixels mm-1 | h = −11→11 |
ω scans | k = −11→11 |
14326 measured reflections | l = −20→21 |
2835 independent reflections |
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) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0504P)2 + 0.2057P] where P = (Fo2 + 2Fc2)/3 |
2835 reflections | (Δ/σ)max < 0.001 |
172 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C15H14N2O | V = 1199.51 (19) Å3 |
Mr = 238.28 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.4891 (7) Å | µ = 0.08 mm−1 |
b = 8.7741 (8) Å | T = 113 K |
c = 16.1351 (16) Å | 0.28 × 0.24 × 0.22 mm |
β = 93.543 (7)° |
Rigaku Saturn diffractometer | 2459 reflections with I > 2σ(I) |
14326 measured reflections | Rint = 0.034 |
2835 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.29 e Å−3 |
2835 reflections | Δρmin = −0.22 e Å−3 |
172 parameters |
Experimental. IR (KBr, cm-1): 3389, 3181, 1663, 1613; 1H NMR (DMSO-d6, 400 MHz) δH: 1.79 (3H, s, CH3), 6.63–6.67 (1H, m, J=0.8, 8.0 Hz, ArH), 6.83 (1H, t, J=0.8, 8.0 Hz, ArH), 6.89 (1H, s, NH), 7.21–7.23 (2H, m, ArH), 7.28–7.32 (2H, m, ArH), 7.61–7.68 (3H, m, ArH), 7.93 (1H, s, NH); 13 C NMR (DMSO-d6, 100 MHz) δC: 31.14, 71.54, 115.36, 116.67, 118.26, 126.09 (2 C), 128.00, 128.45, 128.87 (2 C), 134.05, 147.95, 148.23, 164.90; MS (ESI): m/z (%) =239.1 (100) [M+H]+; C15H14N2O: calcd. C 75.61, H 5.92, N 11.76; found C 75.28, H 6.11, N 11.43. |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.41106 (9) | 0.13177 (9) | −0.08264 (4) | 0.0236 (2) | |
N1 | 0.44850 (10) | 0.16028 (10) | 0.05706 (5) | 0.0173 (2) | |
N2 | 0.38757 (11) | 0.38938 (10) | 0.12264 (6) | 0.0208 (2) | |
C1 | 0.38879 (12) | 0.20563 (11) | −0.01835 (6) | 0.0168 (2) | |
C2 | 0.30141 (12) | 0.35144 (11) | −0.02015 (6) | 0.0165 (2) | |
C3 | 0.30957 (12) | 0.44441 (11) | 0.05098 (6) | 0.0180 (2) | |
C4 | 0.24352 (13) | 0.59131 (12) | 0.04600 (7) | 0.0245 (2) | |
H4 | 0.2517 | 0.6571 | 0.0928 | 0.029* | |
C5 | 0.16659 (14) | 0.63954 (13) | −0.02730 (8) | 0.0285 (3) | |
H5 | 0.1215 | 0.7387 | −0.0302 | 0.034* | |
C6 | 0.15378 (13) | 0.54548 (13) | −0.09718 (7) | 0.0261 (3) | |
H6 | 0.0983 | 0.5792 | −0.1467 | 0.031* | |
C7 | 0.22271 (12) | 0.40276 (12) | −0.09347 (6) | 0.0206 (2) | |
H7 | 0.2165 | 0.3390 | −0.1412 | 0.025* | |
C8 | 0.39390 (12) | 0.22450 (11) | 0.13376 (6) | 0.0170 (2) | |
C9 | 0.23069 (12) | 0.15939 (11) | 0.15239 (6) | 0.0174 (2) | |
C10 | 0.15071 (13) | 0.22173 (13) | 0.21771 (7) | 0.0236 (2) | |
H10 | 0.1973 | 0.3033 | 0.2493 | 0.028* | |
C11 | 0.00388 (15) | 0.16596 (14) | 0.23708 (8) | 0.0304 (3) | |
H11 | −0.0489 | 0.2090 | 0.2818 | 0.036* | |
C12 | −0.06521 (14) | 0.04741 (14) | 0.19100 (8) | 0.0321 (3) | |
H12 | −0.1659 | 0.0099 | 0.2036 | 0.038* | |
C13 | 0.01311 (14) | −0.01636 (14) | 0.12637 (8) | 0.0289 (3) | |
H13 | −0.0340 | −0.0977 | 0.0949 | 0.035* | |
C14 | 0.16110 (13) | 0.03889 (12) | 0.10750 (7) | 0.0220 (2) | |
H14 | 0.2147 | −0.0061 | 0.0637 | 0.026* | |
C15 | 0.51453 (13) | 0.18452 (13) | 0.20463 (7) | 0.0234 (2) | |
H15A | 0.6170 | 0.2290 | 0.1935 | 0.035* | |
H15B | 0.5247 | 0.0735 | 0.2089 | 0.035* | |
H15C | 0.4792 | 0.2254 | 0.2569 | 0.035* | |
H1 | 0.4966 (17) | 0.0719 (18) | 0.0626 (9) | 0.036 (4)* | |
H2 | 0.3890 (18) | 0.4458 (18) | 0.1676 (9) | 0.040 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0313 (4) | 0.0223 (4) | 0.0173 (4) | 0.0078 (3) | 0.0024 (3) | −0.0011 (3) |
N1 | 0.0186 (4) | 0.0162 (4) | 0.0171 (4) | 0.0044 (3) | 0.0014 (3) | 0.0000 (3) |
N2 | 0.0263 (5) | 0.0155 (4) | 0.0201 (5) | 0.0012 (4) | −0.0037 (4) | −0.0032 (3) |
C1 | 0.0162 (5) | 0.0168 (5) | 0.0177 (5) | 0.0000 (4) | 0.0017 (4) | 0.0010 (4) |
C2 | 0.0153 (5) | 0.0149 (5) | 0.0194 (5) | 0.0000 (4) | 0.0017 (4) | 0.0018 (4) |
C3 | 0.0164 (5) | 0.0161 (5) | 0.0214 (5) | −0.0014 (4) | 0.0017 (4) | 0.0013 (4) |
C4 | 0.0292 (6) | 0.0161 (5) | 0.0285 (6) | 0.0017 (4) | 0.0026 (5) | −0.0017 (4) |
C5 | 0.0316 (6) | 0.0180 (5) | 0.0361 (7) | 0.0071 (4) | 0.0030 (5) | 0.0049 (5) |
C6 | 0.0262 (6) | 0.0255 (6) | 0.0264 (6) | 0.0049 (4) | −0.0018 (5) | 0.0079 (4) |
C7 | 0.0197 (5) | 0.0214 (5) | 0.0207 (5) | 0.0001 (4) | 0.0007 (4) | 0.0021 (4) |
C8 | 0.0197 (5) | 0.0154 (5) | 0.0154 (5) | 0.0027 (4) | −0.0010 (4) | −0.0011 (4) |
C9 | 0.0189 (5) | 0.0176 (5) | 0.0155 (5) | 0.0045 (4) | −0.0007 (4) | 0.0047 (4) |
C10 | 0.0275 (6) | 0.0226 (5) | 0.0208 (5) | 0.0083 (4) | 0.0032 (4) | 0.0048 (4) |
C11 | 0.0305 (6) | 0.0319 (6) | 0.0302 (6) | 0.0140 (5) | 0.0128 (5) | 0.0137 (5) |
C12 | 0.0212 (6) | 0.0344 (7) | 0.0412 (7) | 0.0046 (5) | 0.0065 (5) | 0.0215 (6) |
C13 | 0.0259 (6) | 0.0267 (6) | 0.0336 (6) | −0.0049 (5) | −0.0024 (5) | 0.0098 (5) |
C14 | 0.0239 (5) | 0.0220 (5) | 0.0200 (5) | −0.0008 (4) | 0.0007 (4) | 0.0030 (4) |
C15 | 0.0241 (5) | 0.0246 (6) | 0.0206 (5) | 0.0044 (4) | −0.0051 (4) | −0.0021 (4) |
O1—C1 | 1.2473 (12) | C7—H7 | 0.9500 |
N1—C1 | 1.3489 (13) | C8—C15 | 1.5279 (14) |
N1—C8 | 1.4612 (13) | C8—C9 | 1.5452 (14) |
N1—H1 | 0.878 (16) | C9—C14 | 1.3924 (15) |
N2—C3 | 1.3834 (13) | C9—C10 | 1.3997 (15) |
N2—C8 | 1.4583 (13) | C10—C11 | 1.3925 (17) |
N2—H2 | 0.878 (15) | C10—H10 | 0.9500 |
C1—C2 | 1.4782 (13) | C11—C12 | 1.3874 (19) |
C2—C7 | 1.3968 (14) | C11—H11 | 0.9500 |
C2—C3 | 1.4062 (14) | C12—C13 | 1.3886 (18) |
C3—C4 | 1.4059 (15) | C12—H12 | 0.9500 |
C4—C5 | 1.3816 (16) | C13—C14 | 1.3976 (16) |
C4—H4 | 0.9500 | C13—H13 | 0.9500 |
C5—C6 | 1.3961 (17) | C14—H14 | 0.9500 |
C5—H5 | 0.9500 | C15—H15A | 0.9800 |
C6—C7 | 1.3820 (15) | C15—H15B | 0.9800 |
C6—H6 | 0.9500 | C15—H15C | 0.9800 |
C1—N1—C8 | 121.94 (8) | N1—C8—C15 | 108.20 (8) |
C1—N1—H1 | 119.9 (9) | N2—C8—C9 | 111.35 (8) |
C8—N1—H1 | 115.1 (9) | N1—C8—C9 | 110.94 (8) |
C3—N2—C8 | 117.47 (9) | C15—C8—C9 | 109.70 (8) |
C3—N2—H2 | 118.4 (10) | C14—C9—C10 | 118.59 (10) |
C8—N2—H2 | 117.3 (10) | C14—C9—C8 | 122.43 (9) |
O1—C1—N1 | 121.94 (9) | C10—C9—C8 | 118.98 (9) |
O1—C1—C2 | 122.35 (9) | C11—C10—C9 | 120.95 (11) |
N1—C1—C2 | 115.66 (9) | C11—C10—H10 | 119.5 |
C7—C2—C3 | 120.07 (9) | C9—C10—H10 | 119.5 |
C7—C2—C1 | 120.58 (9) | C12—C11—C10 | 119.85 (11) |
C3—C2—C1 | 119.13 (9) | C12—C11—H11 | 120.1 |
N2—C3—C4 | 122.43 (10) | C10—C11—H11 | 120.1 |
N2—C3—C2 | 118.46 (9) | C11—C12—C13 | 119.90 (11) |
C4—C3—C2 | 119.07 (10) | C11—C12—H12 | 120.1 |
C5—C4—C3 | 119.70 (10) | C13—C12—H12 | 120.1 |
C5—C4—H4 | 120.2 | C12—C13—C14 | 120.16 (11) |
C3—C4—H4 | 120.2 | C12—C13—H13 | 119.9 |
C4—C5—C6 | 121.29 (10) | C14—C13—H13 | 119.9 |
C4—C5—H5 | 119.4 | C9—C14—C13 | 120.55 (10) |
C6—C5—H5 | 119.4 | C9—C14—H14 | 119.7 |
C7—C6—C5 | 119.27 (10) | C13—C14—H14 | 119.7 |
C7—C6—H6 | 120.4 | C8—C15—H15A | 109.5 |
C5—C6—H6 | 120.4 | C8—C15—H15B | 109.5 |
C6—C7—C2 | 120.53 (10) | H15A—C15—H15B | 109.5 |
C6—C7—H7 | 119.7 | C8—C15—H15C | 109.5 |
C2—C7—H7 | 119.7 | H15A—C15—H15C | 109.5 |
N2—C8—N1 | 106.82 (8) | H15B—C15—H15C | 109.5 |
N2—C8—C15 | 109.74 (8) | ||
C8—N1—C1—O1 | −165.49 (9) | C3—N2—C8—C15 | 167.04 (9) |
C8—N1—C1—C2 | 17.02 (14) | C3—N2—C8—C9 | −71.30 (11) |
O1—C1—C2—C7 | 8.20 (15) | C1—N1—C8—N2 | −45.85 (12) |
N1—C1—C2—C7 | −174.31 (9) | C1—N1—C8—C15 | −163.94 (9) |
O1—C1—C2—C3 | −166.39 (10) | C1—N1—C8—C9 | 75.67 (12) |
N1—C1—C2—C3 | 11.10 (14) | N2—C8—C9—C14 | 127.89 (10) |
C8—N2—C3—C4 | 155.35 (10) | N1—C8—C9—C14 | 9.06 (13) |
C8—N2—C3—C2 | −26.98 (14) | C15—C8—C9—C14 | −110.43 (11) |
C7—C2—C3—N2 | 179.56 (9) | N2—C8—C9—C10 | −53.28 (12) |
C1—C2—C3—N2 | −5.82 (14) | N1—C8—C9—C10 | −172.12 (9) |
C7—C2—C3—C4 | −2.69 (15) | C15—C8—C9—C10 | 68.40 (11) |
C1—C2—C3—C4 | 171.93 (9) | C14—C9—C10—C11 | −0.68 (15) |
N2—C3—C4—C5 | −179.80 (10) | C8—C9—C10—C11 | −179.55 (9) |
C2—C3—C4—C5 | 2.54 (16) | C9—C10—C11—C12 | −0.31 (16) |
C3—C4—C5—C6 | −0.44 (18) | C10—C11—C12—C13 | 0.76 (17) |
C4—C5—C6—C7 | −1.56 (18) | C11—C12—C13—C14 | −0.19 (17) |
C5—C6—C7—C2 | 1.42 (17) | C10—C9—C14—C13 | 1.25 (15) |
C3—C2—C7—C6 | 0.71 (16) | C8—C9—C14—C13 | −179.92 (9) |
C1—C2—C7—C6 | −173.83 (10) | C12—C13—C14—C9 | −0.82 (17) |
C3—N2—C8—N1 | 49.96 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.878 (16) | 1.970 (16) | 2.8456 (12) | 174.4 (13) |
Symmetry code: (i) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C15H14N2O |
Mr | 238.28 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 113 |
a, b, c (Å) | 8.4891 (7), 8.7741 (8), 16.1351 (16) |
β (°) | 93.543 (7) |
V (Å3) | 1199.51 (19) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.28 × 0.24 × 0.22 |
Data collection | |
Diffractometer | Rigaku Saturn diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14326, 2835, 2459 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.101, 1.11 |
No. of reflections | 2835 |
No. of parameters | 172 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.29, −0.22 |
Computer programs: CrystalClear (Rigaku, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.878 (16) | 1.970 (16) | 2.8456 (12) | 174.4 (13) |
Symmetry code: (i) −x+1, −y, −z. |
1,2-Dihydroquinazolin-4(3H)-ones are much important and useful nitrogen-containing heterocycles due to their diverse biological activities. They have been widely used as antitumors, α-adrenoceptors antagonists, diuretics, herbicides and plant growth relugators (Jackson et al., 2007). The present investigation is aimed at the study of the molecular and supramolecular architecture of the title compound, (I), and may serve as a forerunner to a study of the correlation of these features with its biological activity.
The molecular structure of (I) is shown in Fig. 1. The bond distances and angles (Table 1) agree with those found in a reported 1,2-dihydroquinazolin-4(3H)-ones (Shi et al., 2004). The 1,3-diaza ring exists in an envelope conformation, similar to that found in 4(3H)-quinazolinone derivatives (Yu et al., 1992; Shi et al., 2003). Two phenyl planes are almost perpendicular to each other with an angle of 85.53 (5)°. The O1 atom is deviated from C2-phenyl plane with 0.4706 Å. The crystal structure is stabilized by N—H···O interactions (Table 2, Fig. 2).