




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808035058/lh2717sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808035058/lh2717Isup2.hkl |
CCDC reference: 709462
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.038
- wR factor = 0.111
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
Alert level C Value of measurement temperature given = 292.000 Value of melting point given = 0.000 PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4B ... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 1000 Deg.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 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 2-ethoxycarbonyliminophosphorane (1.27 g, 3 mmol) in 10 ml anhydrous THF, 4-chlorophenylisocyanate (0.46 g, 3 mmol) was added dropwise at room temperature. The reaction mixture was left unstirred for 6 h at 273–278 K, whereafter the above resulting solution was added dropwise to a solution of ethylenediamine (0.18 g, 3 mmol) in 5 ml anhydrous THF. After that, the reaction mixture was stirred overnight, the reaction mixture was cooled and the reaction product was recrystallized from CH3OH—CH2Cl2 to give colorless crystals of the title compound in yield 85%, which were suitable for X-ray analysis.
H atoms bonded to C atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and included in the riding model approximation. The positional parameters of H atoms bonded to N atoms were refined independently. For all H atoms Uiso (H) = 1.2Uiso (C,N).
Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C16H15FN4O | Z = 2 |
Mr = 298.32 | F(000) = 312 |
Triclinic, P1 | Dx = 1.407 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2836 (8) Å | Cell parameters from 2276 reflections |
b = 9.3103 (10) Å | θ = 2.2–28.9° |
c = 9.4952 (10) Å | µ = 0.10 mm−1 |
α = 89.36 (1)° | T = 292 K |
β = 80.537 (10)° | Block, colourless |
γ = 77.163 (10)° | 0.20 × 0.10 × 0.10 mm |
V = 704.03 (13) Å3 |
Bruker SMART APEX CCD diffractometer | 2726 independent reflections |
Radiation source: fine-focus sealed tube | 2318 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.012 |
ω scans | θmax = 26.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −9→10 |
Tmin = 0.970, Tmax = 0.990 | k = −11→11 |
4078 measured reflections | l = −11→11 |
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)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.111 | w = 1/[σ2(Fo2) + (0.0572P)2 + 0.1074P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
2726 reflections | Δρmax = 0.16 e Å−3 |
209 parameters | Δρmin = −0.15 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: 0.033 (5) |
C16H15FN4O | γ = 77.163 (10)° |
Mr = 298.32 | V = 704.03 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.2836 (8) Å | Mo Kα radiation |
b = 9.3103 (10) Å | µ = 0.10 mm−1 |
c = 9.4952 (10) Å | T = 292 K |
α = 89.36 (1)° | 0.20 × 0.10 × 0.10 mm |
β = 80.537 (10)° |
Bruker SMART APEX CCD diffractometer | 2726 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2318 reflections with I > 2σ(I) |
Tmin = 0.970, Tmax = 0.990 | Rint = 0.012 |
4078 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.111 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.16 e Å−3 |
2726 reflections | Δρmin = −0.15 e Å−3 |
209 parameters |
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 | ||
C1 | 0.26560 (18) | 0.91647 (15) | 0.45066 (18) | 0.0596 (4) | |
C2 | 0.1522 (2) | 0.87525 (15) | 0.37986 (16) | 0.0589 (4) | |
H2 | 0.1451 | 0.9031 | 0.2863 | 0.071* | |
C3 | 0.04783 (17) | 0.79107 (14) | 0.45047 (14) | 0.0503 (3) | |
H3 | −0.0308 | 0.7624 | 0.4040 | 0.060* | |
C4 | 0.05872 (15) | 0.74874 (13) | 0.58961 (14) | 0.0449 (3) | |
C5 | 0.17665 (17) | 0.79171 (15) | 0.65820 (16) | 0.0536 (3) | |
H5 | 0.1860 | 0.7632 | 0.7512 | 0.064* | |
C6 | 0.28049 (18) | 0.87722 (16) | 0.58782 (18) | 0.0604 (4) | |
H6 | 0.3590 | 0.9074 | 0.6333 | 0.073* | |
C7 | −0.02621 (15) | 0.55612 (14) | 0.74400 (13) | 0.0424 (3) | |
C8 | 0.15458 (16) | 0.37171 (14) | 0.83809 (13) | 0.0444 (3) | |
C9 | 0.31903 (18) | 0.30166 (17) | 0.85105 (16) | 0.0573 (4) | |
H9 | 0.4075 | 0.3440 | 0.8121 | 0.069* | |
C10 | 0.3511 (2) | 0.17169 (18) | 0.92037 (17) | 0.0670 (4) | |
H10 | 0.4613 | 0.1260 | 0.9272 | 0.080* | |
C11 | 0.2208 (2) | 0.10669 (18) | 0.98092 (18) | 0.0690 (4) | |
H11 | 0.2438 | 0.0177 | 1.0271 | 0.083* | |
C12 | 0.0591 (2) | 0.17479 (17) | 0.97182 (16) | 0.0587 (4) | |
H12 | −0.0284 | 0.1326 | 1.0136 | 0.070* | |
C13 | 0.02374 (16) | 0.30663 (14) | 0.90063 (13) | 0.0459 (3) | |
C14 | −0.14830 (17) | 0.37725 (15) | 0.88772 (14) | 0.0479 (3) | |
C15 | −0.33989 (16) | 0.58408 (16) | 0.79762 (15) | 0.0523 (3) | |
H15A | −0.3462 | 0.6893 | 0.8010 | 0.063* | |
H15B | −0.4153 | 0.5613 | 0.8799 | 0.063* | |
C16 | −0.39955 (16) | 0.54589 (16) | 0.66308 (16) | 0.0555 (4) | |
H16A | −0.3651 | 0.4403 | 0.6447 | 0.067* | |
H16B | −0.5212 | 0.5731 | 0.6772 | 0.067* | |
F1 | 0.36536 (13) | 1.00298 (12) | 0.38271 (13) | 0.0901 (4) | |
N1 | −0.06114 (14) | 0.67357 (13) | 0.65917 (13) | 0.0496 (3) | |
H1 | −0.151 (2) | 0.6763 (17) | 0.6150 (16) | 0.060* | |
N2 | 0.12716 (13) | 0.49763 (12) | 0.75954 (11) | 0.0459 (3) | |
H4A | −0.2947 (19) | 0.5633 (17) | 0.4621 (17) | 0.055* | |
H4B | −0.411 (2) | 0.6934 (17) | 0.5178 (15) | 0.055* | |
N3 | −0.16619 (13) | 0.50507 (12) | 0.80814 (11) | 0.0448 (3) | |
N4 | −0.33145 (16) | 0.62199 (16) | 0.53930 (14) | 0.0590 (3) | |
O1 | −0.27139 (13) | 0.33072 (12) | 0.94041 (12) | 0.0654 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0477 (8) | 0.0456 (7) | 0.0809 (10) | −0.0143 (6) | 0.0073 (7) | 0.0107 (7) |
C2 | 0.0648 (9) | 0.0473 (7) | 0.0579 (8) | −0.0098 (7) | 0.0053 (7) | 0.0068 (6) |
C3 | 0.0511 (8) | 0.0419 (7) | 0.0559 (8) | −0.0093 (6) | −0.0050 (6) | 0.0015 (6) |
C4 | 0.0364 (6) | 0.0387 (6) | 0.0566 (7) | −0.0069 (5) | −0.0015 (5) | 0.0050 (5) |
C5 | 0.0434 (7) | 0.0536 (8) | 0.0647 (8) | −0.0136 (6) | −0.0081 (6) | 0.0092 (6) |
C6 | 0.0413 (7) | 0.0536 (8) | 0.0880 (11) | −0.0148 (6) | −0.0097 (7) | 0.0079 (7) |
C7 | 0.0381 (7) | 0.0470 (7) | 0.0433 (6) | −0.0146 (5) | −0.0034 (5) | 0.0022 (5) |
C8 | 0.0434 (7) | 0.0514 (7) | 0.0409 (6) | −0.0159 (6) | −0.0071 (5) | 0.0053 (5) |
C9 | 0.0435 (8) | 0.0697 (9) | 0.0620 (8) | −0.0185 (7) | −0.0115 (6) | 0.0179 (7) |
C10 | 0.0518 (9) | 0.0761 (10) | 0.0731 (10) | −0.0097 (8) | −0.0183 (7) | 0.0242 (8) |
C11 | 0.0698 (10) | 0.0655 (10) | 0.0738 (10) | −0.0170 (8) | −0.0177 (8) | 0.0287 (8) |
C12 | 0.0584 (9) | 0.0619 (9) | 0.0592 (8) | −0.0235 (7) | −0.0063 (7) | 0.0159 (7) |
C13 | 0.0462 (7) | 0.0517 (7) | 0.0421 (6) | −0.0177 (6) | −0.0050 (5) | 0.0039 (5) |
C14 | 0.0447 (7) | 0.0547 (7) | 0.0460 (7) | −0.0201 (6) | −0.0007 (5) | 0.0026 (6) |
C15 | 0.0348 (7) | 0.0582 (8) | 0.0595 (8) | −0.0086 (6) | 0.0028 (6) | 0.0021 (6) |
C16 | 0.0334 (7) | 0.0580 (8) | 0.0755 (9) | −0.0106 (6) | −0.0095 (6) | 0.0043 (7) |
F1 | 0.0763 (7) | 0.0820 (7) | 0.1149 (9) | −0.0407 (6) | 0.0059 (6) | 0.0289 (6) |
N1 | 0.0379 (6) | 0.0532 (7) | 0.0607 (7) | −0.0154 (5) | −0.0099 (5) | 0.0125 (5) |
N2 | 0.0382 (6) | 0.0514 (6) | 0.0498 (6) | −0.0157 (5) | −0.0054 (4) | 0.0094 (5) |
N3 | 0.0353 (6) | 0.0517 (6) | 0.0476 (6) | −0.0142 (5) | −0.0013 (4) | 0.0029 (5) |
N4 | 0.0429 (7) | 0.0710 (8) | 0.0621 (8) | −0.0101 (6) | −0.0096 (6) | 0.0019 (6) |
O1 | 0.0476 (6) | 0.0723 (7) | 0.0788 (7) | −0.0275 (5) | 0.0011 (5) | 0.0166 (5) |
C1—C2 | 1.362 (2) | C10—C11 | 1.392 (2) |
C1—F1 | 1.3626 (16) | C10—H10 | 0.9300 |
C1—C6 | 1.366 (2) | C11—C12 | 1.365 (2) |
C2—C3 | 1.3819 (19) | C11—H11 | 0.9300 |
C2—H2 | 0.9300 | C12—C13 | 1.3914 (19) |
C3—C4 | 1.3859 (19) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13—C14 | 1.4551 (19) |
C4—C5 | 1.388 (2) | C14—O1 | 1.2254 (15) |
C4—N1 | 1.4123 (16) | C14—N3 | 1.3955 (17) |
C5—C6 | 1.3870 (19) | C15—N3 | 1.4821 (16) |
C5—H5 | 0.9300 | C15—C16 | 1.516 (2) |
C6—H6 | 0.9300 | C15—H15A | 0.9700 |
C7—N2 | 1.2980 (16) | C15—H15B | 0.9700 |
C7—N1 | 1.3581 (17) | C16—N4 | 1.464 (2) |
C7—N3 | 1.3956 (15) | C16—H16A | 0.9700 |
C8—N2 | 1.3785 (16) | C16—H16B | 0.9700 |
C8—C9 | 1.3981 (19) | N1—H1 | 0.908 (17) |
C8—C13 | 1.4023 (18) | N4—H4A | 0.889 (16) |
C9—C10 | 1.366 (2) | N4—H4B | 0.872 (16) |
C9—H9 | 0.9300 | ||
C2—C1—F1 | 118.49 (14) | C10—C11—H11 | 120.3 |
C2—C1—C6 | 122.61 (13) | C11—C12—C13 | 120.67 (14) |
F1—C1—C6 | 118.88 (15) | C11—C12—H12 | 119.7 |
C1—C2—C3 | 118.37 (14) | C13—C12—H12 | 119.7 |
C1—C2—H2 | 120.8 | C12—C13—C8 | 120.13 (13) |
C3—C2—H2 | 120.8 | C12—C13—C14 | 120.69 (12) |
C2—C3—C4 | 120.93 (13) | C8—C13—C14 | 119.18 (12) |
C2—C3—H3 | 119.5 | O1—C14—N3 | 120.70 (12) |
C4—C3—H3 | 119.5 | O1—C14—C13 | 124.22 (13) |
C3—C4—C5 | 119.19 (12) | N3—C14—C13 | 115.08 (11) |
C3—C4—N1 | 117.79 (12) | N3—C15—C16 | 113.90 (11) |
C5—C4—N1 | 122.81 (12) | N3—C15—H15A | 108.8 |
C6—C5—C4 | 119.92 (14) | C16—C15—H15A | 108.8 |
C6—C5—H5 | 120.0 | N3—C15—H15B | 108.8 |
C4—C5—H5 | 120.0 | C16—C15—H15B | 108.8 |
C1—C6—C5 | 118.98 (14) | H15A—C15—H15B | 107.7 |
C1—C6—H6 | 120.5 | N4—C16—C15 | 111.68 (12) |
C5—C6—H6 | 120.5 | N4—C16—H16A | 109.3 |
N2—C7—N1 | 120.96 (11) | C15—C16—H16A | 109.3 |
N2—C7—N3 | 124.41 (11) | N4—C16—H16B | 109.3 |
N1—C7—N3 | 114.62 (11) | C15—C16—H16B | 109.3 |
N2—C8—C9 | 119.28 (12) | H16A—C16—H16B | 107.9 |
N2—C8—C13 | 122.38 (12) | C7—N1—C4 | 124.69 (11) |
C9—C8—C13 | 118.27 (12) | C7—N1—H1 | 114.5 (10) |
C10—C9—C8 | 120.65 (14) | C4—N1—H1 | 115.2 (10) |
C10—C9—H9 | 119.7 | C7—N2—C8 | 117.77 (11) |
C8—C9—H9 | 119.7 | C14—N3—C7 | 121.02 (11) |
C9—C10—C11 | 120.84 (14) | C14—N3—C15 | 116.82 (11) |
C9—C10—H10 | 119.6 | C7—N3—C15 | 122.16 (11) |
C11—C10—H10 | 119.6 | C16—N4—H4A | 112.6 (10) |
C12—C11—C10 | 119.42 (14) | C16—N4—H4B | 109.1 (10) |
C12—C11—H11 | 120.3 | H4A—N4—H4B | 106.8 (14) |
F1—C1—C2—C3 | −178.16 (12) | C8—C13—C14—O1 | −178.72 (13) |
C6—C1—C2—C3 | 0.4 (2) | C12—C13—C14—N3 | −177.09 (12) |
C1—C2—C3—C4 | −0.4 (2) | C8—C13—C14—N3 | 1.78 (18) |
C2—C3—C4—C5 | −0.1 (2) | N3—C15—C16—N4 | −78.30 (15) |
C2—C3—C4—N1 | 174.74 (12) | N2—C7—N1—C4 | −4.7 (2) |
C3—C4—C5—C6 | 0.7 (2) | N3—C7—N1—C4 | 176.42 (11) |
N1—C4—C5—C6 | −173.93 (12) | C3—C4—N1—C7 | 138.77 (13) |
C2—C1—C6—C5 | 0.2 (2) | C5—C4—N1—C7 | −46.58 (19) |
F1—C1—C6—C5 | 178.68 (12) | N1—C7—N2—C8 | −174.97 (11) |
C4—C5—C6—C1 | −0.7 (2) | N3—C7—N2—C8 | 3.84 (19) |
N2—C8—C9—C10 | −175.78 (14) | C9—C8—N2—C7 | 176.85 (12) |
C13—C8—C9—C10 | 1.3 (2) | C13—C8—N2—C7 | −0.13 (19) |
C8—C9—C10—C11 | −0.6 (3) | O1—C14—N3—C7 | −177.93 (12) |
C9—C10—C11—C12 | −0.6 (3) | C13—C14—N3—C7 | 1.58 (17) |
C10—C11—C12—C13 | 1.2 (3) | O1—C14—N3—C15 | 3.07 (19) |
C11—C12—C13—C8 | −0.5 (2) | C13—C14—N3—C15 | −177.42 (11) |
C11—C12—C13—C14 | 178.40 (13) | N2—C7—N3—C14 | −4.69 (19) |
N2—C8—C13—C12 | 176.23 (12) | N1—C7—N3—C14 | 174.18 (11) |
C9—C8—C13—C12 | −0.8 (2) | N2—C7—N3—C15 | 174.25 (12) |
N2—C8—C13—C14 | −2.65 (19) | N1—C7—N3—C15 | −6.87 (17) |
C9—C8—C13—C14 | −179.65 (12) | C16—C15—N3—C14 | −96.27 (14) |
C12—C13—C14—O1 | 2.4 (2) | C16—C15—N3—C7 | 84.75 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N4 | 0.908 (17) | 1.925 (17) | 2.8049 (17) | 162.8 (14) |
N4—H4A···N2i | 0.889 (16) | 2.323 (16) | 3.1321 (18) | 151.4 (13) |
C3—H3···Cgi | 0.93 | 2.77 (1) | 3.4741 (15) | 132 (1) |
Symmetry code: (i) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C16H15FN4O |
Mr | 298.32 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 292 |
a, b, c (Å) | 8.2836 (8), 9.3103 (10), 9.4952 (10) |
α, β, γ (°) | 89.36 (1), 80.537 (10), 77.163 (10) |
V (Å3) | 704.03 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.20 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.970, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4078, 2726, 2318 |
Rint | 0.012 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.111, 1.05 |
No. of reflections | 2726 |
No. of parameters | 209 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.16, −0.15 |
Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N4 | 0.908 (17) | 1.925 (17) | 2.8049 (17) | 162.8 (14) |
N4—H4A···N2i | 0.889 (16) | 2.323 (16) | 3.1321 (18) | 151.4 (13) |
C3—H3···Cgi | 0.93000 | 2.769 (12) | 3.4741 (15) | 132.0 (10) |
Symmetry code: (i) −x, −y+1, −z+1. |
Quinazolinones and their derivatives are now known to have a wide range of useful biological properties, such as hypnotic, sedative, analgesic, anti-convulsant, anti-tussive, anti-bacterial, anti-diabetic, anti-inflammatory and anti-tumor (Armarego, 1963; Witt & Bergman, 2003). In connection with our ongoing heterocyclic synthesis and drug discovery project (Yang et al., 2008), we have focused our research on the synthesis of quinazolinones and pyrazolo pyrimidinones. Herein, the title compound was synthesized and its crystal structure was determined.
In the molecule (Fig. 1), the dihedral angle between the fluorophenyl and pyrimidinone ring is 52.34 (7)°, and the dihedral angle between the fused benzene ring and pyrimidinone ring is 3.30 (6)°. The torsion angles of N2–C7–N1–C4 and N3–C7–N1–C4 are -4.7 (2) and 176.42 (11)°, respectively.
An intramolecular N-H···N hydrogen bond may, in part, influence the conformation of the molecule. In the crystal structure, intermolecular N-H···N hydrogen bonds and weak C–H···π(arene) interactions link pairs of molecules into centrosymmetric dimers (see Table 1 and Fig. 2).