In the title compound, C
17H
13N
3O
2, the two phenyl rings are approximately orthogonal. Intermolecular N—H
O hydrogen bonds generate dimers. The crystal structure is stabilized by N—H
O hydrogen bonds, and C—H
π and N—H
π interactions.
Supporting information
CCDC reference: 259852
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.002 Å
- R factor = 0.037
- wR factor = 0.105
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H3A .. CGP .. 2.90 Ang.
PLAT480_ALERT_4_B Long H...A H-Bond Reported H3C .. CGP .. 2.90 Ang.
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.61 mm
PLAT481_ALERT_4_C Long D...A H-Bond Reported N3 .. CGP .. 3.34 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C3 .. CGP .. 3.69 Ang.
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
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
4 ALERT type 4 Improvement, methodology, query or suggestion
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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).
1-amino-5-benzoyl-4-phenylpyrimidin-2(1
H)-one
top
Crystal data top
C17H13N3O2 | F(000) = 608 |
Mr = 291.30 | Dx = 1.383 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 10310 reflections |
a = 11.7547 (11) Å | θ = 1.8–28.9° |
b = 16.6566 (11) Å | µ = 0.09 mm−1 |
c = 7.2986 (6) Å | T = 296 K |
β = 101.722 (7)° | Prism, light yellow |
V = 1399.2 (2) Å3 | 0.61 × 0.46 × 0.23 mm |
Z = 4 | |
Data collection top
STOE IPDS-II diffractometer | 2612 reflections with I > 2σ(I) |
Radiation source: sealed X-ray tube | Rint = 0.029 |
Plane graphite monochromator | θmax = 28.8°, θmin = 1.8° |
Detector resolution: 6.67 pixels mm-1 | h = −15→15 |
ω scans | k = −22→22 |
9982 measured reflections | l = −9→7 |
3605 independent reflections | |
Refinement top
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)] = 0.037 | All H-atom parameters refined |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0564P)2 + 0.0428P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3605 reflections | Δρmax = 0.15 e Å−3 |
252 parameters | Δρmin = −0.13 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.033 (4) |
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 | |
N1 | 0.58123 (8) | 0.17479 (6) | 0.02078 (14) | 0.0448 (2) | |
N2 | 0.50825 (8) | 0.11459 (6) | 0.26760 (14) | 0.0421 (2) | |
N3 | 0.43127 (10) | 0.11393 (7) | 0.39451 (17) | 0.0506 (3) | |
H3A | 0.3604 (16) | 0.1057 (9) | 0.321 (2) | 0.070 (5)* | |
H3B | 0.4333 (15) | 0.1657 (12) | 0.445 (3) | 0.081 (5)* | |
O1 | 0.42618 (8) | 0.22736 (5) | 0.12324 (14) | 0.0561 (3) | |
O2 | 0.72262 (9) | −0.05651 (5) | −0.01925 (12) | 0.0572 (3) | |
C1 | 0.85852 (11) | 0.10648 (8) | −0.0205 (2) | 0.0522 (3) | |
H1C | 0.8822 (13) | 0.0837 (9) | 0.103 (2) | 0.063 (4)* | |
C2 | 0.94163 (13) | 0.12410 (10) | −0.1242 (2) | 0.0629 (4) | |
H2C | 1.0232 (18) | 0.1119 (10) | −0.077 (3) | 0.081 (5)* | |
C3 | 0.90939 (14) | 0.15934 (9) | −0.2974 (2) | 0.0663 (4) | |
H3C | 0.9649 (17) | 0.1718 (11) | −0.371 (3) | 0.092 (6)* | |
C4 | 0.79406 (15) | 0.17706 (8) | −0.3692 (2) | 0.0616 (4) | |
H4C | 0.7692 (14) | 0.2029 (10) | −0.490 (3) | 0.073 (5)* | |
C5 | 0.71059 (12) | 0.16006 (7) | −0.26599 (19) | 0.0508 (3) | |
H5C | 0.6316 (13) | 0.1735 (8) | −0.3113 (19) | 0.050 (4)* | |
C6 | 0.74220 (10) | 0.12465 (7) | −0.09104 (17) | 0.0429 (3) | |
C7 | 0.65388 (9) | 0.11461 (6) | 0.02669 (16) | 0.0402 (2) | |
C8 | 0.50037 (9) | 0.17586 (7) | 0.13203 (17) | 0.0429 (3) | |
C9 | 0.58059 (10) | 0.05214 (7) | 0.27156 (17) | 0.0419 (3) | |
H9C | 0.5739 (11) | 0.0104 (8) | 0.3658 (19) | 0.045 (3)* | |
C10 | 0.65380 (9) | 0.04737 (7) | 0.14822 (16) | 0.0404 (2) | |
C11 | 0.71652 (10) | −0.02907 (6) | 0.13330 (16) | 0.0413 (2) | |
C12 | 0.76959 (9) | −0.07185 (6) | 0.30807 (16) | 0.0391 (2) | |
C13 | 0.76558 (10) | −0.15524 (7) | 0.31283 (18) | 0.0440 (3) | |
H13C | 0.7241 (12) | −0.1846 (8) | 0.203 (2) | 0.051 (4)* | |
C14 | 0.81859 (11) | −0.19559 (7) | 0.4731 (2) | 0.0503 (3) | |
H14C | 0.8149 (12) | −0.2545 (9) | 0.479 (2) | 0.059 (4)* | |
C15 | 0.87739 (12) | −0.15385 (8) | 0.6260 (2) | 0.0548 (3) | |
H15C | 0.9159 (14) | −0.1825 (9) | 0.738 (2) | 0.068 (4)* | |
C16 | 0.88069 (12) | −0.07113 (9) | 0.6228 (2) | 0.0562 (3) | |
H16C | 0.9220 (15) | −0.0405 (10) | 0.730 (2) | 0.074 (5)* | |
C17 | 0.82607 (11) | −0.02995 (7) | 0.46508 (18) | 0.0487 (3) | |
H17C | 0.8269 (12) | 0.0291 (9) | 0.4603 (19) | 0.057 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0394 (5) | 0.0473 (5) | 0.0490 (6) | 0.0059 (4) | 0.0119 (4) | 0.0048 (4) |
N2 | 0.0365 (5) | 0.0478 (5) | 0.0435 (5) | 0.0050 (4) | 0.0118 (4) | 0.0021 (4) |
N3 | 0.0438 (6) | 0.0620 (7) | 0.0504 (6) | 0.0060 (5) | 0.0196 (5) | 0.0008 (5) |
O1 | 0.0490 (5) | 0.0571 (5) | 0.0648 (6) | 0.0180 (4) | 0.0173 (4) | 0.0079 (4) |
O2 | 0.0740 (6) | 0.0534 (5) | 0.0454 (5) | 0.0046 (4) | 0.0152 (4) | −0.0068 (4) |
C1 | 0.0404 (6) | 0.0599 (7) | 0.0572 (8) | −0.0018 (5) | 0.0118 (6) | −0.0020 (6) |
C2 | 0.0451 (7) | 0.0721 (9) | 0.0758 (10) | −0.0078 (6) | 0.0223 (7) | −0.0127 (8) |
C3 | 0.0684 (9) | 0.0642 (8) | 0.0779 (10) | −0.0170 (7) | 0.0421 (8) | −0.0128 (7) |
C4 | 0.0838 (10) | 0.0522 (7) | 0.0562 (8) | −0.0032 (7) | 0.0315 (8) | 0.0008 (6) |
C5 | 0.0563 (7) | 0.0486 (6) | 0.0502 (7) | 0.0048 (5) | 0.0171 (6) | 0.0031 (5) |
C6 | 0.0420 (6) | 0.0410 (5) | 0.0476 (6) | −0.0011 (4) | 0.0134 (5) | −0.0021 (5) |
C7 | 0.0351 (5) | 0.0435 (6) | 0.0412 (6) | 0.0008 (4) | 0.0058 (4) | −0.0001 (4) |
C8 | 0.0372 (5) | 0.0450 (6) | 0.0460 (6) | 0.0042 (4) | 0.0072 (5) | 0.0016 (5) |
C9 | 0.0386 (5) | 0.0451 (6) | 0.0423 (6) | 0.0030 (4) | 0.0089 (5) | 0.0024 (5) |
C10 | 0.0358 (5) | 0.0437 (5) | 0.0418 (6) | 0.0024 (4) | 0.0078 (4) | 0.0005 (4) |
C11 | 0.0392 (5) | 0.0422 (5) | 0.0436 (6) | −0.0010 (4) | 0.0114 (5) | −0.0030 (5) |
C12 | 0.0346 (5) | 0.0402 (5) | 0.0444 (6) | 0.0027 (4) | 0.0121 (4) | −0.0013 (4) |
C13 | 0.0426 (6) | 0.0409 (5) | 0.0513 (7) | −0.0003 (4) | 0.0164 (5) | −0.0025 (5) |
C14 | 0.0506 (6) | 0.0433 (6) | 0.0613 (8) | 0.0030 (5) | 0.0218 (6) | 0.0080 (5) |
C15 | 0.0504 (7) | 0.0618 (8) | 0.0529 (8) | 0.0086 (6) | 0.0122 (6) | 0.0115 (6) |
C16 | 0.0542 (7) | 0.0609 (8) | 0.0495 (8) | 0.0048 (6) | 0.0010 (6) | −0.0029 (6) |
C17 | 0.0491 (6) | 0.0421 (6) | 0.0528 (7) | 0.0030 (5) | 0.0055 (5) | −0.0042 (5) |
Geometric parameters (Å, º) top
N1—C7 | 1.3118 (14) | C5—H5C | 0.947 (14) |
N1—C8 | 1.3699 (15) | C6—C7 | 1.4855 (15) |
N2—C9 | 1.3401 (14) | C7—C10 | 1.4289 (15) |
N2—C8 | 1.4112 (15) | C9—C10 | 1.3683 (15) |
N2—N3 | 1.4204 (13) | C9—H9C | 0.993 (13) |
N3—H3A | 0.905 (18) | C10—C11 | 1.4863 (15) |
N3—H3B | 0.936 (19) | C11—C12 | 1.4835 (16) |
O1—C8 | 1.2157 (13) | C12—C17 | 1.3899 (17) |
O2—C11 | 1.2191 (14) | C12—C13 | 1.3905 (16) |
C1—C2 | 1.3835 (19) | C13—C14 | 1.3825 (18) |
C1—C6 | 1.3929 (17) | C13—H13C | 0.982 (14) |
C1—H1C | 0.966 (16) | C14—C15 | 1.376 (2) |
C2—C3 | 1.375 (2) | C14—H14C | 0.983 (15) |
C2—H2C | 0.97 (2) | C15—C16 | 1.379 (2) |
C3—C4 | 1.382 (2) | C15—H15C | 0.975 (17) |
C3—H3C | 0.95 (2) | C16—C17 | 1.3814 (19) |
C4—C5 | 1.3824 (19) | C16—H16C | 0.979 (17) |
C4—H4C | 0.968 (18) | C17—H17C | 0.984 (15) |
C5—C6 | 1.3870 (17) | | |
| | | |
C7—N1—C8 | 121.05 (10) | O1—C8—N2 | 119.44 (11) |
C9—N2—C8 | 121.83 (10) | N1—C8—N2 | 116.84 (9) |
C9—N2—N3 | 117.73 (10) | N2—C9—C10 | 120.80 (11) |
C8—N2—N3 | 120.20 (9) | N2—C9—H9C | 114.8 (7) |
N2—N3—H3A | 104.2 (11) | C10—C9—H9C | 124.4 (7) |
N2—N3—H3B | 106.3 (11) | C9—C10—C7 | 116.27 (10) |
H3A—N3—H3B | 108.6 (15) | C9—C10—C11 | 119.06 (10) |
C2—C1—C6 | 120.07 (14) | C7—C10—C11 | 124.27 (10) |
C2—C1—H1C | 119.5 (9) | O2—C11—C12 | 120.85 (10) |
C6—C1—H1C | 120.4 (9) | O2—C11—C10 | 120.68 (11) |
C3—C2—C1 | 120.00 (14) | C12—C11—C10 | 118.46 (9) |
C3—C2—H2C | 118.9 (11) | C17—C12—C13 | 119.60 (11) |
C1—C2—H2C | 121.1 (11) | C17—C12—C11 | 120.98 (10) |
C2—C3—C4 | 120.38 (13) | C13—C12—C11 | 119.39 (10) |
C2—C3—H3C | 121.3 (12) | C14—C13—C12 | 119.67 (12) |
C4—C3—H3C | 118.3 (12) | C14—C13—H13C | 121.0 (8) |
C5—C4—C3 | 119.97 (15) | C12—C13—H13C | 119.4 (8) |
C5—C4—H4C | 117.9 (10) | C15—C14—C13 | 120.43 (12) |
C3—C4—H4C | 122.1 (10) | C15—C14—H14C | 119.3 (9) |
C4—C5—C6 | 120.11 (13) | C13—C14—H14C | 120.2 (9) |
C4—C5—H5C | 121.0 (8) | C14—C15—C16 | 120.16 (13) |
C6—C5—H5C | 118.8 (8) | C14—C15—H15C | 120.2 (9) |
C5—C6—C1 | 119.46 (11) | C16—C15—H15C | 119.6 (9) |
C5—C6—C7 | 119.50 (11) | C15—C16—C17 | 120.02 (13) |
C1—C6—C7 | 120.72 (11) | C15—C16—H16C | 121.2 (10) |
N1—C7—C10 | 122.47 (10) | C17—C16—H16C | 118.7 (10) |
N1—C7—C6 | 114.95 (10) | C16—C17—C12 | 120.08 (12) |
C10—C7—C6 | 122.41 (10) | C16—C17—H17C | 121.3 (8) |
O1—C8—N1 | 123.68 (11) | C12—C17—H17C | 118.6 (8) |
| | | |
C6—C1—C2—C3 | −0.2 (2) | N2—C9—C10—C7 | 4.23 (16) |
C1—C2—C3—C4 | −0.3 (2) | N2—C9—C10—C11 | −168.85 (11) |
C2—C3—C4—C5 | 0.6 (2) | N1—C7—C10—C9 | −5.75 (17) |
C3—C4—C5—C6 | −0.5 (2) | C6—C7—C10—C9 | 169.24 (10) |
C4—C5—C6—C1 | 0.04 (18) | N1—C7—C10—C11 | 166.92 (11) |
C4—C5—C6—C7 | 173.57 (11) | C6—C7—C10—C11 | −18.09 (17) |
C2—C1—C6—C5 | 0.33 (19) | C9—C10—C11—O2 | 135.53 (12) |
C2—C1—C6—C7 | −173.12 (12) | C7—C10—C11—O2 | −36.96 (17) |
C8—N1—C7—C10 | −0.24 (17) | C9—C10—C11—C12 | −43.39 (15) |
C8—N1—C7—C6 | −175.58 (10) | C7—C10—C11—C12 | 144.13 (11) |
C5—C6—C7—N1 | −38.95 (15) | O2—C11—C12—C17 | 140.80 (12) |
C1—C6—C7—N1 | 134.50 (12) | C10—C11—C12—C17 | −40.29 (15) |
C5—C6—C7—C10 | 145.71 (12) | O2—C11—C12—C13 | −37.33 (16) |
C1—C6—C7—C10 | −40.84 (17) | C10—C11—C12—C13 | 141.58 (11) |
C7—N1—C8—O1 | −174.93 (11) | C17—C12—C13—C14 | −0.52 (17) |
C7—N1—C8—N2 | 7.36 (16) | C11—C12—C13—C14 | 177.63 (10) |
C9—N2—C8—O1 | 173.33 (11) | C12—C13—C14—C15 | −1.46 (18) |
N3—N2—C8—O1 | −0.98 (17) | C13—C14—C15—C16 | 2.1 (2) |
C9—N2—C8—N1 | −8.86 (16) | C14—C15—C16—C17 | −0.8 (2) |
N3—N2—C8—N1 | 176.83 (10) | C15—C16—C17—C12 | −1.2 (2) |
C8—N2—C9—C10 | 2.95 (17) | C13—C12—C17—C16 | 1.86 (18) |
N3—N2—C9—C10 | 177.40 (11) | C11—C12—C17—C16 | −176.27 (11) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O2i | 0.91 (2) | 2.37 (2) | 3.110 (2) | 140 (1) |
N3—H3B···O1ii | 0.92 (2) | 2.22 (2) | 3.134 (2) | 166 (2) |
N3—H3A···CgPiii | 0.91 (2) | 2.90 (2) | 3.341 (1) | 112 (1) |
C3—H3C···CgPiv | 0.95 (2) | 2.90 (2) | 3.692 (2) | 142 (2) |
Symmetry codes: (i) −x+1, −y, −z; (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y, −z+1; (iv) −x+2, −y, −z. |