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The title compound, C24H18N4O3, has a planar bicyclic imidazolo[5,4-d]pyrimidine core. The planes of the phenyl and methoxy­phen­oxy substituents form substantial (>30°) dihedral angles with the imidazolopyrimidine plane. Inter­molecular C—H...O inter­actions link the mol­ecules into infinite chains running along the a axis of the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806002765/ya6274sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806002765/ya6274Isup2.hkl
Contains datablock I

CCDC reference: 601279

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.044
  • wR factor = 0.096
  • Data-to-parameter ratio = 9.5

checkCIF/PLATON results

No syntax errors found



Alert level C ABSMU01_ALERT_1_C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.094 Value of mu given = 0.090 STRVA01_ALERT_4_C Flack test results are meaningless. From the CIF: _refine_ls_abs_structure_Flack 0.000 From the CIF: _refine_ls_abs_structure_Flack_su 1.000 PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 1.00 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 1.00
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.00 From the CIF: _reflns_number_total 2677 Count of symmetry unique reflns 2730 Completeness (_total/calc) 98.06% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 4 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

2-(4-Methoxyphenoxy)-1,9-diphenyl-1,9-dihydropurin-6-one top
Crystal data top
C24H18N4O3Dx = 1.380 Mg m3
Mr = 410.42Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 2809 reflections
a = 8.0020 (7) Åθ = 2.2–21.4°
b = 9.7745 (8) ŵ = 0.09 mm1
c = 25.255 (2) ÅT = 292 K
V = 1975.3 (3) Å3Block, colorless
Z = 40.30 × 0.22 × 0.20 mm
F(000) = 856
Data collection top
Bruker SMART CCD area-detector
diffractometer
1958 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.061
Graphite monochromatorθmax = 28.0°, θmin = 1.6°
φ and ω scansh = 1010
12700 measured reflectionsk = 1212
2677 independent reflectionsl = 2332
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0474P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max = 0.001
2677 reflectionsΔρmax = 0.14 e Å3
281 parametersΔρmin = 0.20 e Å3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.0 (10)
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
C11.1875 (5)1.0966 (4)0.69021 (12)0.0877 (11)
H1A1.27171.03350.70190.132*
H1B1.22771.14620.65990.132*
H1C1.08821.04720.68080.132*
C21.0940 (3)1.1398 (3)0.77882 (10)0.0551 (7)
C31.0625 (3)1.0048 (3)0.78992 (10)0.0535 (6)
H31.08310.93800.76450.064*
C41.0001 (3)0.9681 (3)0.83907 (9)0.0524 (6)
H40.97820.87680.84690.063*
C50.9712 (3)1.0675 (3)0.87596 (9)0.0480 (6)
C61.0053 (4)1.2028 (3)0.86524 (10)0.0575 (7)
H60.98611.26970.89070.069*
C71.0678 (4)1.2372 (3)0.81667 (11)0.0650 (8)
H71.09291.32810.80930.078*
C80.7736 (3)0.9875 (3)0.94026 (9)0.0484 (6)
C90.8539 (3)1.0759 (3)1.02728 (9)0.0470 (6)
C101.0007 (3)1.0118 (3)1.04056 (10)0.0552 (7)
H101.02490.92531.02730.066*
C111.1114 (4)1.0769 (4)1.07361 (11)0.0716 (9)
H111.21281.03581.08190.086*
C121.0722 (5)1.2028 (4)1.09441 (11)0.0844 (11)
H121.14581.24561.11760.101*
C130.9244 (5)1.2657 (3)1.08107 (13)0.0807 (10)
H130.89811.35061.09550.097*
C140.8150 (4)1.2036 (3)1.04645 (10)0.0623 (7)
H140.71691.24721.03630.075*
C150.5816 (3)0.9637 (2)1.01569 (9)0.0464 (6)
C160.4780 (3)0.8984 (2)0.97720 (9)0.0457 (6)
C170.5323 (3)0.8849 (2)0.92620 (9)0.0436 (6)
C180.2820 (3)0.7993 (3)0.93647 (10)0.0539 (6)
H180.18060.75770.92850.065*
C190.3986 (3)0.7724 (2)0.84561 (9)0.0460 (6)
C200.3157 (3)0.6529 (3)0.83439 (10)0.0562 (7)
H200.26960.60060.86150.067*
C210.3017 (4)0.6113 (3)0.78224 (11)0.0649 (8)
H210.24480.53080.77450.078*
C220.3693 (4)0.6854 (3)0.74211 (11)0.0634 (7)
H220.35700.65710.70720.076*
C230.4564 (4)0.8034 (3)0.75390 (10)0.0646 (8)
H230.50650.85310.72680.078*
C240.4699 (4)0.8481 (3)0.80554 (10)0.0575 (7)
H240.52670.92870.81320.069*
N10.6802 (3)0.9273 (2)0.90514 (7)0.0487 (5)
N20.7354 (3)1.0076 (2)0.99272 (7)0.0461 (5)
N30.3194 (3)0.8440 (2)0.98375 (8)0.0552 (6)
N40.4061 (3)0.8193 (2)0.89938 (7)0.0471 (5)
O11.1508 (3)1.1891 (2)0.73130 (7)0.0790 (6)
O20.9243 (2)1.0390 (2)0.92850 (6)0.0642 (6)
O30.5531 (2)0.98329 (19)1.06255 (6)0.0568 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.093 (3)0.115 (3)0.0552 (18)0.004 (2)0.0265 (18)0.0066 (19)
C20.0481 (15)0.0701 (17)0.0473 (14)0.0059 (14)0.0027 (12)0.0100 (13)
C30.0546 (16)0.0621 (16)0.0438 (14)0.0045 (14)0.0024 (11)0.0068 (12)
C40.0573 (16)0.0525 (14)0.0473 (14)0.0070 (12)0.0003 (12)0.0012 (11)
C50.0381 (13)0.0700 (16)0.0357 (12)0.0060 (13)0.0007 (10)0.0014 (12)
C60.0531 (16)0.0634 (16)0.0561 (16)0.0001 (14)0.0007 (13)0.0136 (13)
C70.073 (2)0.0589 (16)0.0628 (18)0.0099 (15)0.0010 (15)0.0036 (14)
C80.0438 (14)0.0624 (15)0.0390 (12)0.0047 (13)0.0022 (11)0.0019 (11)
C90.0490 (15)0.0569 (15)0.0352 (12)0.0066 (12)0.0036 (10)0.0018 (11)
C100.0549 (16)0.0688 (17)0.0420 (13)0.0035 (14)0.0007 (12)0.0003 (12)
C110.0579 (18)0.111 (3)0.0455 (16)0.0156 (19)0.0070 (13)0.0029 (17)
C120.074 (2)0.129 (3)0.0498 (17)0.047 (2)0.0051 (17)0.018 (2)
C130.094 (3)0.080 (2)0.068 (2)0.031 (2)0.0219 (19)0.0266 (16)
C140.0637 (18)0.0652 (17)0.0580 (16)0.0104 (15)0.0113 (14)0.0094 (14)
C150.0464 (14)0.0512 (14)0.0416 (14)0.0052 (12)0.0043 (11)0.0019 (11)
C160.0431 (14)0.0515 (13)0.0425 (13)0.0008 (12)0.0043 (11)0.0015 (11)
C170.0414 (14)0.0488 (13)0.0408 (13)0.0007 (11)0.0003 (11)0.0008 (10)
C180.0426 (15)0.0627 (16)0.0564 (15)0.0077 (13)0.0024 (12)0.0026 (13)
C190.0412 (14)0.0547 (14)0.0422 (13)0.0019 (12)0.0061 (11)0.0026 (11)
C200.0551 (16)0.0616 (16)0.0520 (15)0.0108 (13)0.0073 (13)0.0049 (12)
C210.0682 (19)0.0655 (17)0.0610 (17)0.0083 (15)0.0146 (15)0.0057 (15)
C220.074 (2)0.0706 (18)0.0454 (14)0.0039 (16)0.0118 (14)0.0042 (14)
C230.075 (2)0.0722 (17)0.0463 (15)0.0020 (16)0.0021 (14)0.0111 (14)
C240.0636 (18)0.0568 (15)0.0520 (15)0.0076 (14)0.0033 (14)0.0005 (13)
N10.0422 (12)0.0649 (13)0.0390 (11)0.0059 (10)0.0031 (9)0.0022 (10)
N20.0451 (11)0.0561 (11)0.0370 (10)0.0023 (10)0.0022 (9)0.0032 (9)
N30.0483 (13)0.0654 (14)0.0518 (13)0.0036 (11)0.0061 (10)0.0007 (11)
N40.0437 (12)0.0531 (11)0.0444 (11)0.0033 (10)0.0008 (9)0.0007 (9)
O10.0916 (16)0.0888 (14)0.0566 (12)0.0147 (13)0.0163 (11)0.0142 (11)
O20.0505 (11)0.1038 (15)0.0381 (9)0.0231 (11)0.0026 (8)0.0050 (9)
O30.0544 (11)0.0768 (12)0.0391 (9)0.0014 (10)0.0074 (8)0.0031 (9)
Geometric parameters (Å, º) top
C1—O11.407 (4)C12—H120.9300
C1—H1A0.9600C13—C141.378 (4)
C1—H1B0.9600C13—H130.9300
C1—H1C0.9600C14—H140.9300
C2—C71.365 (4)C15—N21.427 (3)
C2—O11.371 (3)C15—O31.220 (3)
C2—C31.373 (4)C15—C161.428 (3)
C3—C41.385 (3)C16—C171.366 (3)
C3—H30.9300C16—N31.386 (3)
C4—C51.366 (3)C17—N11.362 (3)
C4—H40.9300C17—N41.375 (3)
C5—C61.377 (4)C18—N31.306 (3)
C5—O21.407 (3)C18—N41.379 (3)
C6—C71.367 (4)C18—H180.9300
C6—H60.9300C19—C201.373 (3)
C7—H70.9300C19—C241.377 (3)
C8—N11.300 (3)C19—N41.434 (3)
C8—N21.374 (3)C20—C211.383 (3)
C8—O21.340 (3)C20—H200.9300
C9—C101.372 (4)C21—C221.358 (4)
C9—C141.374 (4)C21—H210.9300
C9—N21.451 (3)C22—C231.380 (4)
C10—C111.373 (4)C22—H220.9300
C10—H100.9300C23—C241.380 (3)
C11—C121.374 (5)C23—H230.9300
C11—H110.9300C24—H240.9300
C12—C131.374 (5)
O1—C1—H1A109.5C9—C14—H14120.7
O1—C1—H1B109.5C13—C14—H14120.7
H1A—C1—H1B109.5O3—C15—N2120.5 (2)
O1—C1—H1C109.5O3—C15—C16128.5 (2)
H1A—C1—H1C109.5N2—C15—C16110.99 (19)
H1B—C1—H1C109.5C17—C16—N3111.5 (2)
C7—C2—O1114.8 (2)C17—C16—C15120.0 (2)
C7—C2—C3119.9 (2)N3—C16—C15128.4 (2)
O1—C2—C3125.2 (3)N1—C17—C16128.0 (2)
C2—C3—C4119.9 (2)N1—C17—N4126.0 (2)
C2—C3—H3120.1C16—C17—N4106.0 (2)
C4—C3—H3120.1N3—C18—N4114.1 (2)
C5—C4—C3119.2 (2)N3—C18—H18122.9
C5—C4—H4120.4N4—C18—H18122.9
C3—C4—H4120.4C20—C19—C24120.4 (2)
C4—C5—C6121.0 (2)C20—C19—N4119.2 (2)
C4—C5—O2123.2 (2)C24—C19—N4120.4 (2)
C6—C5—O2115.4 (2)C19—C20—C21119.0 (2)
C7—C6—C5119.0 (2)C19—C20—H20120.5
C7—C6—H6120.5C21—C20—H20120.5
C5—C6—H6120.5C22—C21—C20121.5 (3)
C2—C7—C6120.9 (3)C22—C21—H21119.3
C2—C7—H7119.6C20—C21—H21119.3
C6—C7—H7119.6C21—C22—C23119.1 (3)
N1—C8—O2122.4 (2)C21—C22—H22120.5
N1—C8—N2126.5 (2)C23—C22—H22120.5
O2—C8—N2111.1 (2)C24—C23—C22120.5 (3)
C10—C9—C14121.5 (3)C24—C23—H23119.7
C10—C9—N2119.8 (2)C22—C23—H23119.7
C14—C9—N2118.8 (2)C19—C24—C23119.5 (2)
C9—C10—C11119.3 (3)C19—C24—H24120.3
C9—C10—H10120.4C23—C24—H24120.3
C11—C10—H10120.4C8—N1—C17111.75 (19)
C10—C11—C12120.0 (3)C8—N2—C15122.7 (2)
C10—C11—H11120.0C8—N2—C9120.0 (2)
C12—C11—H11120.0C15—N2—C9117.23 (18)
C13—C12—C11120.2 (3)C18—N3—C16103.2 (2)
C13—C12—H12119.9C17—N4—C18105.07 (19)
C11—C12—H12119.9C17—N4—C19130.3 (2)
C12—C13—C14120.3 (3)C18—N4—C19124.6 (2)
C12—C13—H13119.8C2—O1—C1119.3 (2)
C14—C13—H13119.8C8—O2—C5121.54 (19)
C9—C14—C13118.7 (3)
C7—C2—C3—C41.7 (4)N2—C8—N1—C170.6 (4)
O1—C2—C3—C4177.9 (2)C16—C17—N1—C80.4 (4)
C2—C3—C4—C50.2 (4)N4—C17—N1—C8179.4 (2)
C3—C4—C5—C60.9 (4)N1—C8—N2—C150.4 (4)
C3—C4—C5—O2173.3 (2)O2—C8—N2—C15179.5 (2)
C4—C5—C6—C70.5 (4)N1—C8—N2—C9179.4 (2)
O2—C5—C6—C7173.5 (2)O2—C8—N2—C90.6 (3)
O1—C2—C7—C6177.5 (3)O3—C15—N2—C8179.7 (2)
C3—C2—C7—C62.1 (4)C16—C15—N2—C80.0 (3)
C5—C6—C7—C21.0 (4)O3—C15—N2—C90.2 (3)
C14—C9—C10—C110.2 (4)C16—C15—N2—C9179.9 (2)
N2—C9—C10—C11179.5 (2)C10—C9—N2—C869.1 (3)
C9—C10—C11—C122.2 (4)C14—C9—N2—C8111.6 (3)
C10—C11—C12—C131.8 (5)C10—C9—N2—C15110.8 (3)
C11—C12—C13—C140.5 (5)C14—C9—N2—C1568.5 (3)
C10—C9—C14—C132.1 (4)N4—C18—N3—C160.7 (3)
N2—C9—C14—C13177.2 (2)C17—C16—N3—C180.1 (3)
C12—C13—C14—C92.4 (4)C15—C16—N3—C18179.1 (2)
O3—C15—C16—C17179.5 (2)N1—C17—N4—C18178.9 (2)
N2—C15—C16—C170.2 (3)C16—C17—N4—C180.9 (3)
O3—C15—C16—N31.4 (4)N1—C17—N4—C193.9 (4)
N2—C15—C16—N3178.9 (2)C16—C17—N4—C19176.3 (2)
N3—C16—C17—N1179.3 (2)N3—C18—N4—C171.0 (3)
C15—C16—C17—N10.0 (4)N3—C18—N4—C19176.4 (2)
N3—C16—C17—N40.5 (3)C20—C19—N4—C17143.9 (3)
C15—C16—C17—N4179.8 (2)C24—C19—N4—C1737.7 (4)
C24—C19—C20—C211.4 (4)C20—C19—N4—C1832.8 (4)
N4—C19—C20—C21177.0 (2)C24—C19—N4—C18145.6 (3)
C19—C20—C21—C220.6 (5)C7—C2—O1—C1177.7 (3)
C20—C21—C22—C231.3 (5)C3—C2—O1—C12.6 (4)
C21—C22—C23—C242.3 (5)N1—C8—O2—C518.8 (4)
C20—C19—C24—C230.5 (4)N2—C8—O2—C5161.1 (2)
N4—C19—C24—C23177.9 (2)C4—C5—O2—C869.5 (3)
C22—C23—C24—C191.4 (4)C6—C5—O2—C8117.7 (3)
O2—C8—N1—C17179.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18···O3i0.932.583.315 (3)137
Symmetry code: (i) x1/2, y+3/2, z+2.
 

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