Download citation
Download citation
link to html
In the title compound, C27H23N3O5, the pyrimidine ring is slightly puckered. The mean plane of the pyrimidine ring forms dihedral angles of 28.26 (10), 55.53 (9) and 55.96 (10)° with the three benzene rings in the mol­ecule. There are intramolecular and intermolecular C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805004149/ob6471sup1.cif
Contains datablocks 3, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805004149/ob64713sup2.hkl
Contains datablock 3

CCDC reference: 269832

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.051
  • wR factor = 0.143
  • Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.70 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.64 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.09 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O3 - C9 .. 6.88 su PLAT480_ALERT_4_C Long H...A H-Bond Reported H15 .. O2 .. 2.64 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C27 H23 N3 O5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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 3 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

5-(4-Methoxybenzoyl)-4-(4-methoxyphenyl)1-[1-(4- methoxyphenyl)ethylidenenamino]pyrimidin-2(1H)-one top
Crystal data top
C27H23N3O5Z = 2
Mr = 469.48F(000) = 492
Triclinic, P1Dx = 1.332 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1127 (7) ÅCell parameters from 15633 reflections
b = 10.9405 (9) Åθ = 2.0–28.8°
c = 13.9263 (11) ŵ = 0.09 mm1
α = 77.147 (7)°T = 296 K
β = 83.542 (7)°Plate, colorless
γ = 76.749 (7)°0.46 × 0.27 × 0.07 mm
V = 1170.54 (17) Å3
Data collection top
Stoe IPDS-2
diffractometer
4119 independent reflections
Radiation source: sealed X-ray tube2655 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.061
Detector resolution: 6.67 pixels mm-1θmax = 25.0°, θmin = 2.0°
w scansh = 99
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1313
Tmin = 0.965, Tmax = 0.994l = 1616
12784 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0787P)2]
where P = (Fo2 + 2Fc2)/3
4119 reflections(Δ/σ)max = 0.001
316 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = 0.19 e Å3
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
xyzUiso*/Ueq
O10.5455 (3)0.3112 (2)0.93913 (12)0.0817 (6)
O20.2904 (2)0.50032 (19)0.50724 (12)0.0710 (5)
O30.2300 (3)1.0589 (2)0.5215 (2)0.1080 (8)
O40.2983 (2)0.65841 (17)0.79851 (11)0.0597 (5)
O51.1885 (3)0.0808 (2)0.84405 (19)0.0965 (7)
N10.3494 (2)0.42094 (19)0.85484 (13)0.0509 (5)
N20.5262 (2)0.34252 (18)0.77080 (13)0.0495 (5)
N30.6249 (3)0.25214 (19)0.76694 (14)0.0556 (5)
C10.2875 (3)0.4783 (2)0.76965 (15)0.0448 (5)
C20.4779 (3)0.3576 (2)0.86157 (16)0.0565 (6)
C30.4664 (3)0.4029 (2)0.68417 (16)0.0498 (5)
H30.50310.39240.62620.060*
C40.3534 (3)0.4792 (2)0.67844 (15)0.0450 (5)
C50.3115 (3)0.5529 (2)0.57783 (16)0.0506 (6)
C60.3001 (3)0.6878 (2)0.56547 (16)0.0512 (6)
C70.1985 (4)0.7406 (3)0.48683 (19)0.0701 (7)
H70.14350.69130.44150.084*
C80.1789 (4)0.8634 (3)0.4757 (2)0.0826 (9)
H80.10870.89670.42380.099*
C90.2622 (4)0.9385 (3)0.5407 (2)0.0746 (8)
C100.3675 (4)0.8899 (3)0.6175 (2)0.0725 (7)
H100.42660.94110.66060.087*
C110.3840 (3)0.7649 (2)0.62953 (18)0.0619 (6)
H110.45320.73160.68200.074*
C120.3106 (5)1.1400 (4)0.5802 (3)0.1132 (12)
H12A0.27661.22070.55880.170*
H12B0.28151.10410.64710.170*
H12C0.43101.15280.57660.170*
C130.1378 (3)0.5313 (2)0.77558 (14)0.0428 (5)
C140.0098 (3)0.5388 (2)0.69996 (15)0.0457 (5)
H140.02040.51290.64210.055*
C150.1311 (3)0.5834 (2)0.70897 (15)0.0475 (5)
H150.21310.58990.65680.057*
C160.1515 (3)0.6189 (2)0.79550 (15)0.0475 (5)
C170.0267 (3)0.6125 (2)0.87214 (16)0.0517 (6)
H170.03900.63700.93030.062*
C180.1160 (3)0.5696 (2)0.86121 (15)0.0499 (6)
H180.19990.56630.91250.060*
C190.3380 (3)0.6786 (3)0.89034 (19)0.0677 (7)
H19A0.44390.70600.88190.102*
H19B0.34690.60000.93860.102*
H19C0.24980.74330.91220.102*
C200.7608 (3)0.2585 (2)0.82336 (17)0.0531 (6)
H200.79030.32190.86070.064*
C210.8695 (3)0.1685 (2)0.83012 (17)0.0506 (5)
C220.8279 (4)0.0664 (3)0.7813 (2)0.0691 (7)
H220.72510.05260.74420.083*
C230.9376 (4)0.0135 (3)0.7876 (2)0.0780 (8)
H230.90940.08060.75380.094*
C241.0897 (3)0.0041 (2)0.8435 (2)0.0651 (7)
C251.1306 (3)0.1018 (3)0.8944 (2)0.0650 (7)
H251.23110.11290.93390.078*
C261.0206 (3)0.1838 (3)0.88632 (19)0.0603 (6)
H261.04970.25120.91980.072*
C271.3447 (5)0.0696 (4)0.9016 (3)0.1079 (12)
H27A1.40080.13540.89510.162*
H27B1.41540.01310.87910.162*
H27C1.32380.07890.96960.162*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0922 (14)0.1245 (17)0.0419 (9)0.0703 (13)0.0084 (9)0.0060 (10)
O20.0947 (14)0.0894 (13)0.0393 (9)0.0383 (11)0.0013 (9)0.0182 (9)
O30.1193 (19)0.0773 (15)0.130 (2)0.0326 (14)0.0009 (16)0.0171 (15)
O40.0563 (10)0.0902 (12)0.0455 (9)0.0392 (9)0.0003 (7)0.0175 (9)
O50.0975 (16)0.0800 (14)0.1268 (19)0.0541 (13)0.0016 (14)0.0183 (13)
N10.0511 (11)0.0656 (12)0.0398 (10)0.0251 (10)0.0077 (8)0.0028 (9)
N20.0514 (11)0.0588 (11)0.0437 (10)0.0248 (9)0.0085 (8)0.0053 (9)
N30.0611 (12)0.0616 (12)0.0512 (11)0.0287 (10)0.0068 (10)0.0084 (9)
C10.0460 (12)0.0500 (12)0.0396 (11)0.0129 (10)0.0051 (9)0.0076 (10)
C20.0609 (15)0.0711 (16)0.0417 (13)0.0302 (13)0.0093 (11)0.0008 (12)
C30.0508 (13)0.0615 (14)0.0405 (12)0.0177 (11)0.0055 (10)0.0099 (11)
C40.0447 (12)0.0544 (13)0.0384 (11)0.0157 (10)0.0055 (9)0.0074 (10)
C50.0465 (12)0.0689 (15)0.0396 (12)0.0209 (11)0.0049 (10)0.0073 (11)
C60.0494 (13)0.0645 (15)0.0387 (11)0.0184 (11)0.0063 (10)0.0001 (11)
C70.0806 (19)0.0816 (19)0.0507 (14)0.0350 (16)0.0087 (13)0.0069 (13)
C80.096 (2)0.083 (2)0.0681 (18)0.0442 (18)0.0164 (16)0.0010 (16)
C90.079 (2)0.0618 (17)0.082 (2)0.0287 (15)0.0124 (16)0.0049 (15)
C100.0767 (18)0.0635 (17)0.0718 (17)0.0109 (14)0.0017 (14)0.0098 (14)
C110.0606 (15)0.0642 (16)0.0544 (14)0.0135 (13)0.0017 (12)0.0008 (12)
C120.112 (3)0.089 (2)0.130 (3)0.010 (2)0.005 (3)0.020 (2)
C130.0445 (12)0.0490 (12)0.0363 (11)0.0141 (10)0.0063 (9)0.0054 (9)
C140.0475 (12)0.0562 (13)0.0350 (11)0.0113 (10)0.0063 (9)0.0105 (10)
C150.0424 (12)0.0613 (14)0.0380 (11)0.0126 (10)0.0008 (9)0.0077 (10)
C160.0471 (12)0.0574 (13)0.0421 (12)0.0203 (11)0.0044 (10)0.0079 (10)
C170.0598 (14)0.0678 (15)0.0370 (11)0.0269 (12)0.0010 (10)0.0174 (11)
C180.0504 (13)0.0648 (15)0.0381 (11)0.0217 (12)0.0031 (10)0.0110 (11)
C190.0701 (17)0.094 (2)0.0551 (15)0.0410 (15)0.0085 (12)0.0213 (14)
C200.0552 (14)0.0547 (14)0.0516 (13)0.0173 (11)0.0101 (11)0.0066 (11)
C210.0526 (13)0.0512 (13)0.0497 (13)0.0173 (11)0.0066 (10)0.0058 (10)
C220.0655 (17)0.0686 (17)0.0800 (18)0.0265 (14)0.0087 (14)0.0231 (15)
C230.085 (2)0.0660 (17)0.095 (2)0.0311 (16)0.0091 (17)0.0318 (16)
C240.0685 (17)0.0575 (15)0.0738 (17)0.0323 (14)0.0087 (14)0.0008 (13)
C250.0595 (15)0.0703 (17)0.0686 (16)0.0266 (13)0.0021 (13)0.0090 (14)
C260.0588 (15)0.0661 (16)0.0613 (15)0.0225 (13)0.0001 (12)0.0161 (13)
C270.092 (3)0.122 (3)0.119 (3)0.073 (2)0.001 (2)0.004 (2)
Geometric parameters (Å, º) top
O1—C21.215 (3)C12—H12B0.9600
O2—C51.223 (3)C12—H12C0.9600
O3—C121.349 (4)C13—C181.391 (3)
O3—C91.363 (3)C13—C141.396 (3)
O4—C161.365 (3)C14—C151.369 (3)
O4—C191.428 (3)C14—H140.9300
O5—C241.357 (3)C15—C161.383 (3)
O5—C271.417 (4)C15—H150.9300
N1—C11.316 (3)C16—C171.388 (3)
N1—C21.362 (3)C17—C181.380 (3)
N2—C31.337 (3)C17—H170.9300
N2—C21.419 (3)C18—H180.9300
N2—N31.420 (2)C19—H19A0.9600
N3—C201.278 (3)C19—H19B0.9600
C1—C41.430 (3)C19—H19C0.9600
C1—C131.478 (3)C20—C211.447 (3)
C3—C41.359 (3)C20—H200.9300
C3—H30.9300C21—C261.376 (3)
C4—C51.498 (3)C21—C221.391 (3)
C5—C61.470 (3)C22—C231.368 (4)
C6—C111.381 (3)C22—H220.9300
C6—C71.395 (3)C23—C241.381 (4)
C7—C81.363 (4)C23—H230.9300
C7—H70.9300C24—C251.370 (4)
C8—C91.374 (4)C25—C261.382 (3)
C8—H80.9300C25—H250.9300
C9—C101.380 (4)C26—H260.9300
C10—C111.376 (4)C27—H27A0.9600
C10—H100.9300C27—H27B0.9600
C11—H110.9300C27—H27C0.9600
C12—H12A0.9600
C12—O3—C9118.1 (3)C14—C13—C1122.69 (18)
C16—O4—C19118.25 (17)C15—C14—C13121.53 (19)
C24—O5—C27118.5 (3)C15—C14—H14119.2
C1—N1—C2122.31 (19)C13—C14—H14119.2
C3—N2—C2121.47 (18)C14—C15—C16120.1 (2)
C3—N2—N3116.41 (18)C14—C15—H15120.0
C2—N2—N3121.76 (18)C16—C15—H15120.0
C20—N3—N2115.2 (2)O4—C16—C15115.74 (19)
N1—C1—C4121.7 (2)O4—C16—C17124.44 (19)
N1—C1—C13114.86 (19)C15—C16—C17119.82 (19)
C4—C1—C13123.25 (19)C18—C17—C16119.39 (19)
O1—C2—N1124.0 (2)C18—C17—H17120.3
O1—C2—N2120.2 (2)C16—C17—H17120.3
N1—C2—N2115.83 (19)C17—C18—C13121.8 (2)
N2—C3—C4121.9 (2)C17—C18—H18119.1
N2—C3—H3119.1C13—C18—H18119.1
C4—C3—H3119.1O4—C19—H19A109.5
C3—C4—C1115.7 (2)O4—C19—H19B109.5
C3—C4—C5116.51 (19)H19A—C19—H19B109.5
C1—C4—C5127.80 (19)O4—C19—H19C109.5
O2—C5—C6121.2 (2)H19A—C19—H19C109.5
O2—C5—C4119.3 (2)H19B—C19—H19C109.5
C6—C5—C4119.44 (19)N3—C20—C21121.0 (2)
C11—C6—C7118.1 (2)N3—C20—H20119.5
C11—C6—C5122.8 (2)C21—C20—H20119.5
C7—C6—C5119.1 (2)C26—C21—C22118.1 (2)
C8—C7—C6120.7 (3)C26—C21—C20119.3 (2)
C8—C7—H7119.7C22—C21—C20122.6 (2)
C6—C7—H7119.7C23—C22—C21120.3 (3)
C7—C8—C9120.4 (3)C23—C22—H22119.9
C7—C8—H8119.8C21—C22—H22119.9
C9—C8—H8119.8C22—C23—C24120.8 (3)
O3—C9—C8114.3 (3)C22—C23—H23119.6
O3—C9—C10125.7 (3)C24—C23—H23119.6
C8—C9—C10120.0 (3)O5—C24—C25124.6 (3)
C11—C10—C9119.3 (3)O5—C24—C23115.6 (2)
C11—C10—H10120.4C25—C24—C23119.7 (2)
C9—C10—H10120.4C24—C25—C26119.2 (2)
C10—C11—C6121.5 (2)C24—C25—H25120.4
C10—C11—H11119.3C26—C25—H25120.4
C6—C11—H11119.3C21—C26—C25121.9 (2)
O3—C12—H12A109.5C21—C26—H26119.1
O3—C12—H12B109.5C25—C26—H26119.1
H12A—C12—H12B109.5O5—C27—H27A109.5
O3—C12—H12C109.5O5—C27—H27B109.5
H12A—C12—H12C109.5H27A—C27—H27B109.5
H12B—C12—H12C109.5O5—C27—H27C109.5
C18—C13—C14117.39 (19)H27A—C27—H27C109.5
C18—C13—C1119.84 (19)H27B—C27—H27C109.5
C3—N2—N3—C20135.3 (2)C9—C10—C11—C61.2 (4)
C2—N2—N3—C2051.5 (3)C7—C6—C11—C100.6 (4)
C2—N1—C1—C40.9 (4)C5—C6—C11—C10178.3 (2)
C2—N1—C1—C13174.3 (2)N1—C1—C13—C1827.9 (3)
C1—N1—C2—O1174.8 (3)C4—C1—C13—C18156.9 (2)
C1—N1—C2—N28.0 (3)N1—C1—C13—C14148.6 (2)
C3—N2—C2—O1173.3 (2)C4—C1—C13—C1426.6 (3)
N3—N2—C2—O113.8 (4)C18—C13—C14—C150.7 (3)
C3—N2—C2—N19.4 (3)C1—C13—C14—C15177.3 (2)
N3—N2—C2—N1163.5 (2)C13—C14—C15—C161.9 (3)
C2—N2—C3—C41.6 (3)C19—O4—C16—C15171.2 (2)
N3—N2—C3—C4171.6 (2)C19—O4—C16—C178.7 (4)
N2—C3—C4—C17.3 (3)C14—C15—C16—O4178.1 (2)
N2—C3—C4—C5173.3 (2)C14—C15—C16—C171.8 (4)
N1—C1—C4—C38.8 (3)O4—C16—C17—C18179.3 (2)
C13—C1—C4—C3166.1 (2)C15—C16—C17—C180.6 (4)
N1—C1—C4—C5171.9 (2)C16—C17—C18—C130.6 (4)
C13—C1—C4—C513.3 (4)C14—C13—C18—C170.6 (3)
C3—C4—C5—O241.5 (3)C1—C13—C18—C17176.1 (2)
C1—C4—C5—O2137.8 (2)N2—N3—C20—C21177.2 (2)
C3—C4—C5—C6137.2 (2)N3—C20—C21—C26175.5 (2)
C1—C4—C5—C643.5 (3)N3—C20—C21—C224.1 (4)
O2—C5—C6—C11153.8 (2)C26—C21—C22—C231.7 (4)
C4—C5—C6—C1124.9 (3)C20—C21—C22—C23177.9 (3)
O2—C5—C6—C727.3 (3)C21—C22—C23—C241.0 (5)
C4—C5—C6—C7154.0 (2)C27—O5—C24—C250.6 (4)
C11—C6—C7—C82.0 (4)C27—O5—C24—C23178.8 (3)
C5—C6—C7—C8177.0 (3)C22—C23—C24—O5179.8 (3)
C6—C7—C8—C91.5 (5)C22—C23—C24—C250.8 (5)
C12—O3—C9—C8178.1 (3)O5—C24—C25—C26178.7 (3)
C12—O3—C9—C102.0 (5)C23—C24—C25—C262.0 (4)
C7—C8—C9—O3179.4 (3)C22—C21—C26—C250.5 (4)
C7—C8—C9—C100.5 (5)C20—C21—C26—C25179.1 (2)
O3—C9—C10—C11178.1 (3)C24—C25—C26—C211.3 (4)
C8—C9—C10—C111.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C20—H20···O10.932.342.737 (3)105
C11—H11···O4i0.932.603.512 (3)166
C3—H3···O2ii0.932.543.330 (3)143
C15—H15···O2iii0.932.643.374 (3)136
Symmetry codes: (i) x1, y, z; (ii) x1, y+1, z+1; (iii) x, y+1, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds