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In the title compound, C16H18N2O3, there is an intra­molecular N—H...O hydrogen bond. Inter­molecular C—H...O bonds stabilize the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806023531/bt2109sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806023531/bt2109Isup2.hkl
Contains datablock I

CCDC reference: 613598

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.037
  • wR factor = 0.111
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.678 1.000 Tmin(prime) and Tmax expected: 0.981 0.987 RR(prime) = 0.682 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.68
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 2 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 2 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: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXTL.

9-(4-methyoxylbenzoyl)-1,2,3,4,7,8-hexahydropyrido[1,2-a]pyrimidin-6-one top
Crystal data top
C16H18N2O3F(000) = 304
Mr = 286.32Dx = 1.365 Mg m3
Triclinic, P1Melting point: 456 K
a = 7.5696 (17) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.725 (2) ÅCell parameters from 1854 reflections
c = 10.446 (2) Åθ = 2.3–26.2°
α = 88.964 (4)°µ = 0.10 mm1
β = 77.971 (4)°T = 294 K
γ = 68.169 (3)°Prism, yellow
V = 696.6 (3) Å30.20 × 0.18 × 0.14 mm
Z = 2
Data collection top
Bruker SMART CCD area detector
diffractometer
2435 independent reflections
Radiation source: fine-focus sealed tube1890 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 96
Tmin = 0.678, Tmax = 1.000k = 1111
3539 measured reflectionsl = 127
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)] = 0.037H-atom parameters constrained
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0568P)2 + 0.1302P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
2435 reflectionsΔρmax = 0.21 e Å3
192 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.052 (7)
Special details top

Experimental. IR (KBr, ν cm-1): 3210, 1686, 1600, 1532; 1H NMR (CDCl3): δ 12.75 (s, 1H), 7.35 (d, 2H), 6.86 (d, 2H), 3.81 (t, 2H), 3.79 (s, 3H), 3.44 (quin, 2H), 2.59 (t, 2H), 2.48 (t, 2H), 2.01 (quin, 2H); 13C NMR (CDCl3): δ 188.4, 170.5, 160.0, 156.4, 134.4, 128.6, 113.0, 87.3, 55.2, 39.0, 38.54, 32.7, 21.9, 20.6.

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
O10.26795 (17)0.63810 (14)0.32339 (12)0.0547 (4)
O20.77597 (17)0.67414 (15)0.06763 (11)0.0585 (4)
O30.16391 (18)1.10132 (13)0.53567 (12)0.0584 (4)
N10.53391 (18)0.62431 (14)0.24966 (12)0.0385 (3)
N20.81149 (18)0.56915 (15)0.16433 (13)0.0426 (4)
H20.86350.58450.10300.051*
C10.6625 (2)0.55846 (19)0.37747 (16)0.0471 (4)
H1A0.70930.63070.42200.056*
H1B0.59020.53050.43180.056*
C20.8327 (2)0.42364 (19)0.35776 (18)0.0507 (4)
H2A0.78650.35060.31410.061*
H2B0.91670.37920.44200.061*
C30.9444 (2)0.47014 (19)0.27571 (16)0.0467 (4)
H3A1.03400.38300.24430.056*
H3B1.02010.52040.32880.056*
C40.6197 (2)0.63839 (16)0.14640 (14)0.0354 (4)
C50.5062 (2)0.72541 (17)0.03131 (15)0.0388 (4)
C60.2898 (2)0.8014 (2)0.02560 (17)0.0483 (4)
H6A0.26450.89530.06640.058*
H6B0.21920.82180.06520.058*
C70.2192 (2)0.7037 (2)0.09598 (17)0.0516 (5)
H7A0.22570.61720.04650.062*
H7B0.08390.75810.09930.062*
C80.3361 (2)0.65422 (17)0.23171 (16)0.0414 (4)
C90.5953 (2)0.74102 (18)0.07076 (15)0.0419 (4)
C100.4766 (2)0.83726 (18)0.19295 (15)0.0399 (4)
C110.3521 (3)0.98521 (19)0.19213 (16)0.0479 (4)
H110.33681.02690.11240.058*
C120.2518 (3)1.07053 (18)0.30734 (17)0.0491 (4)
H120.17141.16930.30480.059*
C130.2704 (2)1.00923 (17)0.42700 (16)0.0426 (4)
C140.3922 (2)0.86246 (17)0.43009 (15)0.0427 (4)
H140.40460.82020.50990.051*
C150.4953 (2)0.77928 (18)0.31359 (15)0.0414 (4)
H150.57950.68170.31640.050*
C160.1724 (3)1.0402 (2)0.66014 (18)0.0607 (5)
H16A0.12810.95930.66480.091*
H16B0.09051.11530.72820.091*
H16C0.30441.00470.67140.091*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0493 (7)0.0660 (8)0.0578 (8)0.0243 (6)0.0254 (6)0.0002 (6)
O20.0423 (7)0.0856 (9)0.0457 (7)0.0183 (6)0.0158 (5)0.0065 (6)
O30.0661 (8)0.0438 (7)0.0500 (7)0.0065 (6)0.0061 (6)0.0054 (6)
N10.0359 (7)0.0453 (8)0.0362 (7)0.0153 (6)0.0123 (6)0.0004 (6)
N20.0345 (7)0.0557 (8)0.0401 (7)0.0172 (6)0.0127 (6)0.0007 (6)
C10.0446 (9)0.0547 (10)0.0400 (9)0.0140 (8)0.0133 (7)0.0039 (8)
C20.0465 (10)0.0472 (10)0.0555 (10)0.0126 (8)0.0135 (8)0.0073 (8)
C30.0373 (9)0.0509 (10)0.0489 (10)0.0124 (7)0.0109 (7)0.0005 (8)
C40.0365 (8)0.0392 (8)0.0358 (8)0.0182 (7)0.0119 (6)0.0072 (7)
C50.0369 (8)0.0462 (9)0.0361 (8)0.0180 (7)0.0097 (7)0.0047 (7)
C60.0386 (9)0.0603 (11)0.0443 (9)0.0164 (8)0.0091 (7)0.0013 (8)
C70.0386 (9)0.0675 (12)0.0536 (10)0.0249 (8)0.0111 (8)0.0042 (9)
C80.0407 (9)0.0399 (9)0.0507 (10)0.0187 (7)0.0184 (8)0.0066 (7)
C90.0415 (9)0.0505 (10)0.0385 (9)0.0226 (8)0.0092 (7)0.0052 (7)
C100.0415 (9)0.0444 (9)0.0402 (9)0.0217 (7)0.0116 (7)0.0030 (7)
C110.0614 (11)0.0472 (10)0.0434 (9)0.0264 (9)0.0182 (8)0.0114 (8)
C120.0581 (11)0.0338 (9)0.0568 (11)0.0157 (8)0.0184 (9)0.0061 (8)
C130.0438 (9)0.0391 (9)0.0455 (9)0.0161 (7)0.0096 (7)0.0014 (7)
C140.0479 (9)0.0413 (9)0.0368 (8)0.0141 (7)0.0100 (7)0.0043 (7)
C150.0426 (9)0.0377 (8)0.0426 (9)0.0124 (7)0.0118 (7)0.0022 (7)
C160.0677 (12)0.0562 (11)0.0471 (10)0.0178 (10)0.0020 (9)0.0063 (9)
Geometric parameters (Å, º) top
O1—C81.2162 (18)C6—C71.516 (2)
O2—C91.2710 (19)C6—H6A0.9700
O3—C131.3634 (19)C6—H6B0.9700
O3—C161.424 (2)C7—C81.487 (2)
N1—C81.387 (2)C7—H7A0.9700
N1—C41.4028 (19)C7—H7B0.9700
N1—C11.472 (2)C9—C101.501 (2)
N2—C41.3266 (19)C10—C151.384 (2)
N2—C31.458 (2)C10—C111.397 (2)
N2—H20.8600C11—C121.378 (2)
C1—C21.506 (2)C11—H110.9300
C1—H1A0.9700C12—C131.386 (2)
C1—H1B0.9700C12—H120.9300
C2—C31.501 (2)C13—C141.386 (2)
C2—H2A0.9700C14—C151.384 (2)
C2—H2B0.9700C14—H140.9300
C3—H3A0.9700C15—H150.9300
C3—H3B0.9700C16—H16A0.9600
C4—C51.402 (2)C16—H16B0.9600
C5—C91.413 (2)C16—H16C0.9600
C5—C61.514 (2)
C13—O3—C16117.53 (13)C8—C7—C6112.51 (14)
C8—N1—C4122.38 (13)C8—C7—H7A109.1
C8—N1—C1118.90 (13)C6—C7—H7A109.1
C4—N1—C1118.30 (12)C8—C7—H7B109.1
C4—N2—C3127.64 (13)C6—C7—H7B109.1
C4—N2—H2116.2H7A—C7—H7B107.8
C3—N2—H2116.2O1—C8—N1120.33 (15)
N1—C1—C2109.79 (13)O1—C8—C7123.80 (15)
N1—C1—H1A109.7N1—C8—C7115.86 (13)
C2—C1—H1A109.7O2—C9—C5123.44 (15)
N1—C1—H1B109.7O2—C9—C10115.86 (14)
C2—C1—H1B109.7C5—C9—C10120.69 (14)
H1A—C1—H1B108.2C15—C10—C11117.63 (15)
C3—C2—C1108.73 (14)C15—C10—C9118.82 (14)
C3—C2—H2A109.9C11—C10—C9123.51 (14)
C1—C2—H2A109.9C12—C11—C10121.22 (15)
C3—C2—H2B109.9C12—C11—H11119.4
C1—C2—H2B109.9C10—C11—H11119.4
H2A—C2—H2B108.3C11—C12—C13120.08 (15)
N2—C3—C2110.48 (13)C11—C12—H12120.0
N2—C3—H3A109.6C13—C12—H12120.0
C2—C3—H3A109.6O3—C13—C14124.35 (14)
N2—C3—H3B109.6O3—C13—C12116.00 (14)
C2—C3—H3B109.6C14—C13—C12119.65 (15)
H3A—C3—H3B108.1C15—C14—C13119.55 (15)
N2—C4—C5122.20 (14)C15—C14—H14120.2
N2—C4—N1117.09 (14)C13—C14—H14120.2
C5—C4—N1120.70 (13)C14—C15—C10121.84 (15)
C4—C5—C9120.05 (14)C14—C15—H15119.1
C4—C5—C6116.57 (13)C10—C15—H15119.1
C9—C5—C6123.37 (14)O3—C16—H16A109.5
C5—C6—C7110.25 (14)O3—C16—H16B109.5
C5—C6—H6A109.6H16A—C16—H16B109.5
C7—C6—H6A109.6O3—C16—H16C109.5
C5—C6—H6B109.6H16A—C16—H16C109.5
C7—C6—H6B109.6H16B—C16—H16C109.5
H6A—C6—H6B108.1
C8—N1—C1—C2128.86 (15)C6—C7—C8—O1144.63 (16)
C4—N1—C1—C243.92 (19)C6—C7—C8—N136.2 (2)
N1—C1—C2—C360.43 (18)C4—C5—C9—O23.3 (2)
C4—N2—C3—C213.9 (2)C6—C5—C9—O2178.04 (15)
C1—C2—C3—N245.34 (19)C4—C5—C9—C10178.24 (14)
C3—N2—C4—C5176.72 (15)C6—C5—C9—C100.4 (2)
C3—N2—C4—N14.9 (2)O2—C9—C10—C1548.9 (2)
C8—N1—C4—N2161.55 (14)C5—C9—C10—C15129.66 (16)
C1—N1—C4—N211.0 (2)O2—C9—C10—C11128.72 (17)
C8—N1—C4—C520.0 (2)C5—C9—C10—C1152.7 (2)
C1—N1—C4—C5167.46 (14)C15—C10—C11—C120.1 (2)
N2—C4—C5—C90.3 (2)C9—C10—C11—C12177.55 (15)
N1—C4—C5—C9178.69 (13)C10—C11—C12—C131.2 (3)
N2—C4—C5—C6178.39 (14)C16—O3—C13—C142.9 (2)
N1—C4—C5—C60.0 (2)C16—O3—C13—C12177.14 (16)
C4—C5—C6—C735.2 (2)C11—C12—C13—O3179.23 (15)
C9—C5—C6—C7146.07 (15)C11—C12—C13—C140.8 (2)
C5—C6—C7—C852.9 (2)O3—C13—C14—C15179.34 (15)
C4—N1—C8—O1178.70 (14)C12—C13—C14—C150.6 (2)
C1—N1—C8—O16.2 (2)C13—C14—C15—C101.7 (2)
C4—N1—C8—C70.5 (2)C11—C10—C15—C141.4 (2)
C1—N1—C8—C7173.00 (15)C9—C10—C15—C14179.13 (14)
 

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