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In the crystal structure of the title compound, C20H19N3O3, only one of the two possible O-enol/O-keto tautomers (7-hydr­oxy-5-oxo) exists. In the guanidine part of the mol­ecule, partial π-electron delocalization between two N—C bonds is observed, while the third C—N bond has some double-bond character. The conformation of the mol­ecule is influenced by intra­molecular C—H...O hydrogen bonds and the steric effect of adjacent carbonyl, benzyl and hydroxyl groups. The mol­ecular packing is influenced by strong inter­molecular O—H...O hydrogen bonds and C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019015/bx2005sup1.cif
Contains datablocks global, Va

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019015/bx2005Vasup2.hkl
Contains datablock Va

CCDC reference: 610726

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.050
  • wR factor = 0.156
  • Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.78 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.66 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C35 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... CGA PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... CGA PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... CGB
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.778 Tmax scaled 0.774 Tmin scaled 0.713
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

6-Benzyl-7-hydroxy-1-(2-methoxyphenyl)-1H,7H-2,3- dihydroimidazo[1,2-a]pyrimidin-5-one top
Crystal data top
C20H19N3O3F(000) = 736
Mr = 349.38Dx = 1.309 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 12.1771 (6) Åθ = 20.8–42.6°
b = 13.2172 (7) ŵ = 0.73 mm1
c = 11.0141 (8) ÅT = 298 K
β = 90.785 (5)°Prism, colourless
V = 1772.52 (18) Å30.59 × 0.42 × 0.35 mm
Z = 4
Data collection top
Enraf–Nonius TurboCAD4
diffractometer
Rint = 0.026
ω/2θ scansθmax = 74.2°, θmin = 3.6°
Absorption correction: ψ scan
(North et al., 1968)
h = 1515
Tmin = 0.917, Tmax = 0.996k = 016
3758 measured reflectionsl = 013
3565 independent reflections3 standard reflections every 100 reflections
1998 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0729P)2 + 0.2545P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.050(Δ/σ)max < 0.001
wR(F2) = 0.157Δρmax = 0.16 e Å3
S = 1.02Δρmin = 0.18 e Å3
3565 reflectionsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
286 parametersExtinction coefficient: 0.0110 (7)
0 restraints
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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

6.5158 (0.0179) x + 7.9839 (0.0193) y - 6.5850 (0.0149) z = 5.2189 (0.0192)

* -0.0253 (0.0021) N1 * 0.0058 (0.0017) C2 * 0.0163 (0.0020) N3 * -0.0286 (0.0023) C4 * 0.0319 (0.0024) C5

Rms deviation of fitted atoms = 0.0236

5.7407 (0.0108) x + 8.4482 (0.0097) y - 6.7629 (0.0077) z = 5.5499 (0.0087)

Angle to previous plane (with approximate e.s.d.) = 4.28 (0.23)

* 0.0092 (0.0017) C2 * -0.0159 (0.0015) N6 * 0.0110 (0.0016) C7 * 0.0005 (0.0016) C8 * -0.0074 (0.0016) C9 * 0.0026 (0.0016) N3 0.0777 (0.0033) O10 0.0231 (0.0031) O11

Rms deviation of fitted atoms = 0.0093

9.1592 (0.0072) x - 5.4469 (0.0156) y + 5.5495 (0.0127) z = 0.8939 (0.0162)

Angle to previous plane (with approximate e.s.d.) = 77.22 (0.08)

* 0.0228 (0.0021) C31 * 0.0154 (0.0025) C32 * -0.0051 (0.0026) C33 * -0.0145 (0.0032) C34 * -0.0071 (0.0030) C35 * 0.0171 (0.0028) C36 * -0.0284 (0.0017) C12

Rms deviation of fitted atoms = 0.0175

- 9.3650 (0.0098) x + 3.2108 (0.0110) y + 6.6270 (0.0115) z = 4.5533 (0.0089)

Angle to previous plane (with approximate e.s.d.) = 68.00 (0.08)

* 0.0077 (0.0022) C21 * 0.0006 (0.0022) C22 * -0.0096 (0.0027) C23 * 0.0022 (0.0026) C24 * 0.0056 (0.0025) C25 * 0.0019 (0.0024) C26 * -0.0084 (0.0017) O27

Rms deviation of fitted atoms = 0.0061

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
O100.22496 (14)0.65132 (13)0.17246 (16)0.0505 (5)
H1010.196 (2)0.630 (2)0.101 (3)0.076*
O110.16583 (14)0.91218 (13)0.45621 (15)0.0511 (5)
O270.16996 (18)0.96309 (16)0.0210 (2)0.0834 (7)
N10.08488 (18)0.85608 (16)0.1653 (2)0.0598 (6)
N30.04357 (17)0.87367 (16)0.30736 (18)0.0500 (5)
N60.06596 (16)0.74216 (14)0.16482 (18)0.0456 (5)
C20.0107 (2)0.81814 (18)0.2091 (2)0.0461 (6)
C40.0335 (3)0.9548 (3)0.3362 (3)0.0692 (9)
H410.004 (3)1.017 (3)0.331 (3)0.104*
H420.066 (3)0.949 (3)0.414 (4)0.104*
C50.1181 (3)0.9465 (3)0.2333 (3)0.0736 (10)
H510.111 (3)1.010 (3)0.171 (3)0.11*
H520.192 (3)0.945 (3)0.261 (3)0.11*
C70.16371 (19)0.72412 (17)0.2213 (2)0.0410 (6)
C80.20456 (19)0.77530 (17)0.3214 (2)0.0425 (6)
C90.14144 (19)0.85504 (18)0.3686 (2)0.0434 (6)
C120.3195 (2)0.7568 (2)0.3715 (2)0.0487 (6)
H1210.345 (2)0.684 (2)0.361 (3)0.073*
H1220.325 (2)0.769 (2)0.462 (3)0.073*
C210.1544 (2)0.8069 (2)0.0791 (2)0.0492 (6)
C220.1806 (2)0.7069 (2)0.0894 (3)0.0610 (8)
H2210.149 (3)0.670 (2)0.155 (3)0.091*
C230.2528 (3)0.6613 (3)0.0080 (3)0.0769 (10)
H2310.270 (3)0.583 (3)0.020 (3)0.115*
C240.2987 (3)0.7185 (3)0.0828 (3)0.0819 (11)
H2410.351 (3)0.688 (2)0.141 (3)0.097 (11)*
C250.2739 (3)0.8183 (3)0.0956 (3)0.0711 (9)
H2510.306 (3)0.861 (3)0.163 (3)0.107*
C260.2007 (2)0.8644 (2)0.0150 (2)0.0558 (7)
C280.2313 (4)1.0289 (3)0.0978 (4)0.1092 (14)
H2810.21021.09760.08170.164*
H2820.30821.02070.08250.164*
H2830.21691.01290.18110.164*
C310.4020 (2)0.82573 (19)0.3122 (2)0.0493 (6)
C320.4507 (2)0.7993 (3)0.2045 (3)0.0629 (8)
H3210.442 (3)0.735 (3)0.175 (3)0.094*
C330.5218 (3)0.8642 (4)0.1473 (4)0.0878 (11)
H3310.558 (4)0.838 (3)0.073 (4)0.132*
C340.5460 (3)0.9562 (4)0.1959 (5)0.0987 (14)
H3410.591 (3)1.005 (3)0.155 (3)0.107 (13)*
C350.4984 (4)0.9838 (3)0.3029 (6)0.1029 (14)
H3510.513 (4)1.045 (4)0.334 (4)0.154*
C360.4272 (3)0.9193 (2)0.3614 (4)0.0749 (9)
H3610.390 (3)0.942 (3)0.436 (4)0.112*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O100.0519 (10)0.0489 (10)0.0504 (10)0.0076 (8)0.0128 (8)0.0052 (8)
O110.0602 (11)0.0521 (10)0.0409 (9)0.0042 (8)0.0099 (8)0.0041 (8)
O270.0835 (15)0.0679 (14)0.0982 (17)0.0028 (12)0.0147 (13)0.0252 (13)
N10.0529 (13)0.0513 (13)0.0745 (15)0.0117 (10)0.0258 (11)0.0141 (12)
N30.0487 (12)0.0516 (13)0.0495 (12)0.0065 (10)0.0116 (9)0.0095 (10)
N60.0461 (11)0.0422 (11)0.0481 (12)0.0038 (9)0.0138 (9)0.0021 (9)
C20.0482 (14)0.0420 (13)0.0476 (14)0.0002 (11)0.0125 (11)0.0016 (11)
C40.0555 (18)0.069 (2)0.083 (2)0.0140 (15)0.0191 (16)0.0263 (18)
C50.0665 (19)0.0670 (19)0.086 (2)0.0209 (17)0.0263 (18)0.0255 (17)
C70.0434 (13)0.0382 (13)0.0411 (13)0.0005 (10)0.0056 (10)0.0070 (10)
C80.0446 (13)0.0413 (13)0.0414 (13)0.0007 (10)0.0091 (10)0.0057 (10)
C90.0478 (13)0.0426 (13)0.0394 (12)0.0056 (11)0.0079 (10)0.0039 (11)
C120.0510 (15)0.0512 (15)0.0436 (14)0.0050 (12)0.0149 (11)0.0037 (12)
C210.0413 (13)0.0515 (14)0.0545 (15)0.0040 (11)0.0121 (11)0.0031 (12)
C220.0603 (17)0.0504 (16)0.072 (2)0.0023 (13)0.0162 (15)0.0007 (14)
C230.064 (2)0.0624 (19)0.104 (3)0.0069 (16)0.0154 (18)0.0180 (18)
C240.0604 (19)0.091 (3)0.093 (3)0.0089 (18)0.0308 (18)0.030 (2)
C250.0634 (19)0.091 (3)0.0579 (18)0.0180 (18)0.0206 (14)0.0019 (17)
C260.0495 (15)0.0618 (17)0.0559 (16)0.0049 (13)0.0047 (12)0.0057 (14)
C280.124 (3)0.099 (3)0.104 (3)0.022 (2)0.000 (3)0.056 (2)
C310.0428 (13)0.0527 (15)0.0521 (15)0.0045 (11)0.0142 (11)0.0014 (12)
C320.0532 (16)0.074 (2)0.0617 (18)0.0026 (15)0.0051 (14)0.0053 (16)
C330.063 (2)0.122 (3)0.079 (2)0.002 (2)0.0053 (18)0.014 (2)
C340.073 (3)0.094 (3)0.128 (4)0.018 (2)0.000 (3)0.033 (3)
C350.088 (3)0.063 (2)0.158 (5)0.020 (2)0.007 (3)0.004 (3)
C360.067 (2)0.0622 (19)0.095 (3)0.0066 (16)0.0072 (18)0.0162 (18)
Geometric parameters (Å, º) top
O10—C71.335 (3)C21—C221.366 (4)
O10—H1010.91 (3)C21—C261.397 (3)
O11—C91.258 (3)C22—C231.385 (4)
O27—C261.359 (3)C22—H2210.94 (3)
O27—C281.418 (4)C23—C241.367 (5)
N1—C21.350 (3)C23—H2311.06 (4)
N1—C211.420 (3)C24—C251.360 (5)
N1—C51.470 (4)C24—H2410.98 (4)
N3—C21.364 (3)C25—C261.391 (4)
N3—C91.384 (3)C25—H2511.00 (4)
N3—C41.463 (4)C28—H2810.96
N6—C21.307 (3)C28—H2820.96
N6—C71.357 (3)C28—H2830.96
C4—C51.525 (4)C31—C321.379 (4)
C4—H410.94 (4)C31—C361.383 (4)
C4—H420.95 (4)C32—C331.377 (5)
C5—H511.09 (4)C32—H3210.92 (3)
C5—H520.95 (4)C33—C341.360 (6)
C7—C81.381 (3)C33—H3310.99 (4)
C8—C91.408 (3)C34—C351.370 (6)
C8—C121.517 (3)C34—H3410.96 (4)
C12—C311.511 (4)C35—C361.382 (6)
C12—H1211.02 (3)C35—H3510.90 (5)
C12—H1221.02 (3)C36—H3610.99 (4)
C7—O10—H101111.4 (19)C26—C21—N1118.5 (2)
C26—O27—C28118.3 (3)C21—C22—C23121.0 (3)
C2—N1—C21124.9 (2)C21—C22—H221118 (2)
C2—N1—C5111.2 (2)C23—C22—H221121 (2)
C21—N1—C5123.1 (2)C24—C23—C22118.9 (3)
C2—N3—C9122.2 (2)C24—C23—H231123 (2)
C2—N3—C4112.6 (2)C22—C23—H231118 (2)
C9—N3—C4125.1 (2)C25—C24—C23121.6 (3)
C2—N6—C7114.7 (2)C25—C24—H241118 (2)
N6—C2—N1126.7 (2)C23—C24—H241120 (2)
N6—C2—N3124.2 (2)C24—C25—C26119.9 (3)
N1—C2—N3109.0 (2)C24—C25—H251123 (2)
N3—C4—C5102.4 (2)C26—C25—H251118 (2)
N3—C4—H41108 (2)O27—C26—C25124.3 (3)
C5—C4—H41110 (2)O27—C26—C21116.7 (2)
N3—C4—H42115 (2)C25—C26—C21119.0 (3)
C5—C4—H42112 (2)O27—C28—H281109.5
H41—C4—H42109 (3)O27—C28—H282109.5
N1—C5—C4104.5 (2)H281—C28—H282109.5
N1—C5—H51106 (2)O27—C28—H283109.5
C4—C5—H51111 (2)H281—C28—H283109.5
N1—C5—H52114 (2)H282—C28—H283109.5
C4—C5—H52113 (2)C32—C31—C36117.9 (3)
H51—C5—H52108 (3)C32—C31—C12121.0 (2)
O10—C7—N6115.7 (2)C36—C31—C12121.0 (3)
O10—C7—C8118.5 (2)C33—C32—C31121.1 (3)
N6—C7—C8125.7 (2)C33—C32—H321119 (2)
C7—C8—C9118.0 (2)C31—C32—H321119 (2)
C7—C8—C12122.1 (2)C34—C33—C32120.8 (4)
C9—C8—C12119.5 (2)C34—C33—H331123 (2)
O11—C9—N3117.4 (2)C32—C33—H331116 (3)
O11—C9—C8127.5 (2)C33—C34—C35119.0 (4)
N3—C9—C8115.1 (2)C33—C34—H341122 (2)
C31—C12—C8111.2 (2)C35—C34—H341118 (2)
C31—C12—H121108.2 (17)C34—C35—C36120.8 (4)
C8—C12—H121113.1 (16)C34—C35—H351119 (3)
C31—C12—H122107.0 (16)C36—C35—H351120 (3)
C8—C12—H122112.3 (17)C35—C36—C31120.5 (4)
H121—C12—H122105 (2)C35—C36—H361120 (2)
C22—C21—C26119.7 (2)C31—C36—H361119 (2)
C22—C21—N1121.7 (2)
C7—N6—C2—N1175.4 (3)C7—C8—C12—C3189.5 (3)
C7—N6—C2—N32.8 (4)C9—C8—C12—C3182.9 (3)
C21—N1—C2—N614.3 (5)C2—N1—C21—C2245.6 (4)
C5—N1—C2—N6175.6 (3)C5—N1—C21—C22123.3 (3)
C21—N1—C2—N3167.2 (2)C2—N1—C21—C26137.4 (3)
C5—N1—C2—N32.9 (3)C5—N1—C21—C2653.7 (4)
C9—N3—C2—N61.2 (4)C26—C21—C22—C230.1 (5)
C4—N3—C2—N6179.4 (3)N1—C21—C22—C23176.8 (3)
C9—N3—C2—N1177.3 (2)C21—C22—C23—C240.7 (5)
C4—N3—C2—N10.8 (3)C22—C23—C24—C250.9 (5)
C2—N3—C4—C53.9 (4)C23—C24—C25—C260.2 (5)
C9—N3—C4—C5174.2 (3)C28—O27—C26—C2513.1 (4)
C2—N1—C5—C45.2 (4)C28—O27—C26—C21166.9 (3)
C21—N1—C5—C4165.0 (3)C24—C25—C26—O27179.3 (3)
N3—C4—C5—N15.2 (4)C24—C25—C26—C210.6 (5)
C2—N6—C7—O10175.6 (2)C22—C21—C26—O27179.2 (3)
C2—N6—C7—C83.1 (3)N1—C21—C26—O273.8 (4)
O10—C7—C8—C9177.1 (2)C22—C21—C26—C250.8 (4)
N6—C7—C8—C91.6 (4)N1—C21—C26—C25176.2 (3)
O10—C7—C8—C124.6 (3)C8—C12—C31—C3286.2 (3)
N6—C7—C8—C12174.1 (2)C8—C12—C31—C3690.8 (3)
C2—N3—C9—O11178.1 (2)C36—C31—C32—C330.4 (4)
C4—N3—C9—O110.2 (4)C12—C31—C32—C33176.7 (3)
C2—N3—C9—C80.5 (3)C31—C32—C33—C340.2 (5)
C4—N3—C9—C8177.5 (3)C32—C33—C34—C350.2 (6)
C7—C8—C9—O11177.7 (2)C33—C34—C35—C360.4 (7)
C12—C8—C9—O115.0 (4)C34—C35—C36—C310.6 (6)
C7—C8—C9—N30.3 (3)C32—C31—C36—C350.6 (5)
C12—C8—C9—N3172.4 (2)C12—C31—C36—C35176.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H51···O271.09 (4)2.31 (3)2.871 (4)110 (3)
O10—H101···O11i0.90 (3)1.72 (3)2.617 (2)169 (2)
C24—H241···CgAii0.98 (4)2.63 (3)3.584 (4)165 (3)
C28—H283···CgAiii0.962.983.562 (5)120
C33—H331···CgBiv0.99 (4)2.94 (5)3.747 (4)139 (3)
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x1, y+3/2, z1/2; (iii) x, y+1, z+1; (iv) x+1, y, z.
 

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