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In the asymmetric unit of the title compound, C16H14N4O, there are two crystallographically independent mol­ecules, which are connected to each other by O—H...N hydrogen bonds, forming a mol­ecular chain. The neighboring chains are linked into a layer through π–π stacking inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806052226/om2077sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806052226/om2077Isup2.hkl
Contains datablock I

CCDC reference: 633981

Key indicators

  • Single-crystal X-ray study
  • T = 250 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.059
  • wR factor = 0.182
  • Data-to-parameter ratio = 20.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for N5 - C29 .. 6.06 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); 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: CrystalStructure and PLATON (Spek, 2003).

N-[5-(1-Naphthyl)pyrimidin-4-yl]acetamide oxime top
Crystal data top
C16H14N4OZ = 4
Mr = 278.31F(000) = 584.00
Triclinic, P1Dx = 1.326 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71075 Å
a = 10.8011 (6) ÅCell parameters from 14565 reflections
b = 11.6051 (6) Åθ = 3.0–30.0°
c = 12.8489 (8) ŵ = 0.09 mm1
α = 63.3951 (16)°T = 250 K
β = 76.8282 (16)°Plate, colorless
γ = 89.5278 (19)°0.38 × 0.30 × 0.10 mm
V = 1394.00 (14) Å3
Data collection top
Rigaku R-AXIS RAPID-II
diffractometer
Rint = 0.065
Detector resolution: 10.00 pixels mm-1θmax = 30.0°
ω scansh = 1515
24844 measured reflectionsk = 1614
8057 independent reflectionsl = 1818
4461 reflections with I > 2σ(I)
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.059 w = 1/[σ2(Fo2) + (0.0969P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.182(Δ/σ)max < 0.001
S = 0.98Δρmax = 0.19 e Å3
8057 reflectionsΔρmin = 0.29 e Å3
396 parameters
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
O10.04449 (11)0.72598 (12)0.02991 (10)0.0559 (3)
O20.47007 (12)0.21978 (13)0.44912 (11)0.0614 (4)
N10.33828 (15)0.35923 (14)0.27913 (13)0.0567 (4)
N20.30864 (12)0.49534 (13)0.08461 (12)0.0476 (3)
N30.11721 (12)0.58780 (12)0.06085 (10)0.0402 (3)
N40.04303 (12)0.69267 (13)0.11028 (10)0.0463 (3)
N50.78779 (15)0.16030 (14)0.83121 (14)0.0587 (4)
N60.78593 (12)0.03469 (14)0.62523 (13)0.0518 (3)
N70.61025 (13)0.07402 (13)0.57141 (11)0.0427 (3)
N80.57076 (13)0.18216 (13)0.38248 (11)0.0513 (3)
C10.01803 (16)0.48307 (15)0.31973 (12)0.0462 (4)
C20.07889 (19)0.38326 (17)0.38622 (14)0.0599 (5)
H20.06440.30070.39500.072*
C30.1996 (2)0.4038 (2)0.44119 (17)0.0710 (6)
H30.26370.33490.48600.085*
C40.22295 (18)0.5247 (2)0.42895 (15)0.0645 (5)
H40.30380.53780.46340.077*
C50.14543 (18)0.75530 (18)0.35143 (15)0.0574 (4)
H50.22590.77060.38460.069*
C60.04983 (19)0.85490 (18)0.29153 (16)0.0616 (5)
H60.06500.93660.28490.074*
C70.07051 (18)0.83380 (17)0.24039 (16)0.0573 (4)
H70.13590.90170.20030.069*
C80.09417 (15)0.71536 (15)0.24816 (14)0.0475 (4)
H80.17520.70390.21240.057*
C90.00263 (15)0.60869 (15)0.30991 (12)0.0430 (3)
C100.12578 (15)0.62982 (16)0.36463 (13)0.0490 (4)
C110.14374 (15)0.45955 (14)0.26067 (13)0.0423 (3)
C120.22162 (17)0.38127 (15)0.32642 (14)0.0526 (4)
H120.19180.34040.40970.063*
C130.37459 (17)0.41987 (16)0.16029 (16)0.0535 (4)
H130.45610.40820.12560.064*
C140.19194 (14)0.51403 (14)0.13353 (12)0.0387 (3)
C150.12498 (14)0.62361 (13)0.05942 (12)0.0385 (3)
C160.22325 (16)0.58013 (17)0.13202 (14)0.0531 (4)
H16A0.22320.48780.08940.080*
H16B0.30600.62170.14570.080*
H16C0.20400.60280.20780.080*
C170.47810 (15)0.01293 (14)0.82413 (12)0.0416 (3)
C180.37447 (17)0.10496 (16)0.88365 (14)0.0524 (4)
H180.38440.18940.89580.063*
C190.25289 (18)0.07460 (18)0.92704 (16)0.0603 (5)
H190.18410.13890.96780.072*
C200.23632 (16)0.04897 (17)0.90920 (14)0.0543 (4)
H200.15570.06860.93690.065*
C210.32672 (16)0.27622 (16)0.82942 (14)0.0522 (4)
H210.24630.29790.85470.063*
C220.42834 (17)0.36959 (17)0.77440 (16)0.0576 (4)
H220.41700.45370.76260.069*
C230.54950 (17)0.33825 (16)0.73590 (16)0.0557 (4)
H230.61880.40190.69940.067*
C240.56796 (15)0.21627 (15)0.75083 (14)0.0465 (4)
H240.64950.19790.72410.056*
C250.46377 (13)0.11615 (14)0.80699 (12)0.0392 (3)
C260.34032 (14)0.14759 (15)0.84902 (12)0.0424 (3)
C270.60582 (14)0.04808 (14)0.78141 (13)0.0417 (3)
C280.67047 (17)0.12698 (16)0.86208 (15)0.0526 (4)
H280.63090.15970.94350.063*
C290.83767 (17)0.11026 (17)0.71363 (18)0.0591 (5)
H290.91930.13080.69010.071*
C300.66898 (14)0.00305 (14)0.65795 (13)0.0410 (3)
C310.63956 (15)0.10959 (14)0.44876 (12)0.0428 (3)
C320.74810 (18)0.06245 (19)0.38940 (15)0.0640 (5)
H32A0.73960.03060.42960.096*
H32B0.82720.09520.39360.096*
H32C0.74750.09230.30670.096*
H1O0.099 (2)0.757 (2)0.072 (2)0.090 (8)*
H3N0.0453 (18)0.6067 (18)0.0991 (17)0.065 (5)*
H2O0.434 (2)0.265 (2)0.390 (2)0.080 (7)*
H7N0.5380 (17)0.0975 (18)0.5978 (17)0.059 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0496 (7)0.0734 (8)0.0426 (6)0.0288 (6)0.0196 (5)0.0214 (6)
O20.0621 (8)0.0756 (8)0.0403 (6)0.0309 (6)0.0227 (6)0.0170 (6)
N10.0686 (10)0.0544 (8)0.0583 (9)0.0242 (7)0.0375 (8)0.0256 (7)
N20.0462 (7)0.0566 (8)0.0445 (7)0.0185 (6)0.0179 (6)0.0242 (6)
N30.0439 (7)0.0478 (7)0.0302 (6)0.0166 (6)0.0139 (5)0.0170 (5)
N40.0466 (7)0.0557 (8)0.0317 (6)0.0137 (6)0.0144 (5)0.0139 (6)
N50.0649 (9)0.0603 (9)0.0686 (10)0.0302 (7)0.0412 (8)0.0338 (8)
N60.0459 (8)0.0641 (9)0.0583 (8)0.0224 (7)0.0207 (6)0.0358 (7)
N70.0428 (7)0.0523 (7)0.0344 (6)0.0168 (6)0.0131 (5)0.0195 (5)
N80.0539 (8)0.0579 (8)0.0336 (6)0.0097 (6)0.0118 (6)0.0135 (6)
C10.0574 (10)0.0505 (9)0.0290 (7)0.0049 (7)0.0132 (6)0.0157 (6)
C20.0774 (13)0.0539 (10)0.0398 (8)0.0077 (9)0.0039 (8)0.0187 (7)
C30.0714 (13)0.0800 (13)0.0474 (10)0.0202 (10)0.0060 (9)0.0264 (9)
C40.0577 (11)0.0882 (14)0.0420 (9)0.0019 (10)0.0014 (8)0.0300 (9)
C50.0586 (11)0.0758 (12)0.0428 (9)0.0229 (9)0.0138 (8)0.0313 (9)
C60.0727 (12)0.0602 (11)0.0580 (10)0.0222 (9)0.0179 (9)0.0318 (9)
C70.0621 (11)0.0530 (10)0.0576 (10)0.0100 (8)0.0113 (8)0.0277 (8)
C80.0475 (9)0.0520 (9)0.0447 (8)0.0085 (7)0.0095 (7)0.0247 (7)
C90.0484 (9)0.0522 (9)0.0309 (7)0.0104 (7)0.0133 (6)0.0196 (6)
C100.0487 (9)0.0669 (10)0.0311 (7)0.0081 (8)0.0080 (7)0.0231 (7)
C110.0546 (9)0.0406 (8)0.0346 (7)0.0096 (6)0.0183 (6)0.0164 (6)
C120.0725 (12)0.0487 (9)0.0383 (8)0.0128 (8)0.0265 (8)0.0157 (7)
C130.0562 (10)0.0599 (10)0.0566 (10)0.0244 (8)0.0281 (8)0.0311 (8)
C140.0435 (8)0.0413 (7)0.0349 (7)0.0126 (6)0.0168 (6)0.0174 (6)
C150.0393 (8)0.0425 (7)0.0289 (6)0.0062 (6)0.0103 (6)0.0115 (6)
C160.0556 (10)0.0680 (10)0.0363 (8)0.0152 (8)0.0105 (7)0.0251 (7)
C170.0477 (8)0.0469 (8)0.0300 (6)0.0094 (7)0.0145 (6)0.0153 (6)
C180.0603 (10)0.0480 (9)0.0426 (8)0.0016 (8)0.0081 (7)0.0176 (7)
C190.0535 (11)0.0667 (11)0.0480 (9)0.0119 (9)0.0032 (8)0.0225 (8)
C200.0447 (9)0.0713 (11)0.0428 (8)0.0032 (8)0.0029 (7)0.0263 (8)
C210.0506 (9)0.0625 (10)0.0470 (9)0.0176 (8)0.0110 (7)0.0289 (8)
C220.0625 (11)0.0501 (9)0.0635 (11)0.0153 (8)0.0135 (9)0.0301 (8)
C230.0548 (10)0.0490 (9)0.0610 (10)0.0049 (8)0.0072 (8)0.0268 (8)
C240.0405 (8)0.0517 (9)0.0494 (9)0.0092 (7)0.0091 (7)0.0261 (7)
C250.0416 (8)0.0472 (8)0.0308 (6)0.0112 (6)0.0121 (6)0.0182 (6)
C260.0405 (8)0.0538 (9)0.0319 (7)0.0090 (7)0.0074 (6)0.0196 (6)
C270.0488 (9)0.0426 (8)0.0393 (7)0.0135 (6)0.0196 (6)0.0197 (6)
C280.0655 (11)0.0530 (9)0.0471 (9)0.0187 (8)0.0292 (8)0.0228 (7)
C290.0536 (10)0.0642 (11)0.0824 (13)0.0292 (8)0.0340 (9)0.0457 (10)
C300.0411 (8)0.0455 (8)0.0430 (8)0.0134 (6)0.0175 (6)0.0227 (6)
C310.0447 (8)0.0475 (8)0.0320 (7)0.0042 (7)0.0071 (6)0.0158 (6)
C320.0649 (12)0.0790 (13)0.0440 (9)0.0191 (9)0.0055 (8)0.0286 (9)
Geometric parameters (Å, º) top
O1—N41.4199 (16)C8—H80.9300
O1—H1O0.86 (2)C9—C101.431 (2)
O2—N81.4175 (17)C11—C121.368 (2)
O2—H2O0.88 (2)C11—C141.4256 (19)
N1—C131.323 (2)C12—H120.9300
N1—C121.344 (2)C13—H130.9300
N2—C131.3277 (19)C15—C161.488 (2)
N2—C141.3369 (18)C16—H16A0.9600
N3—C141.3684 (18)C16—H16B0.9600
N3—C151.3907 (17)C16—H16C0.9600
N3—H3N0.901 (18)C17—C181.370 (2)
N4—C151.2790 (18)C17—C251.426 (2)
N5—C291.326 (2)C17—C271.489 (2)
N5—C281.346 (2)C18—C191.412 (2)
N6—C291.327 (2)C18—H180.9300
N6—C301.3401 (18)C19—C201.364 (2)
N7—C301.3638 (18)C19—H190.9300
N7—C311.3951 (18)C20—C261.415 (2)
N7—H7N0.870 (18)C20—H200.9300
N8—C311.274 (2)C21—C221.363 (2)
C1—C21.376 (2)C21—C261.411 (2)
C1—C91.426 (2)C21—H210.9300
C1—C111.485 (2)C22—C231.396 (2)
C2—C31.407 (3)C22—H220.9300
C2—H20.9300C23—C241.360 (2)
C3—C41.368 (3)C23—H230.9300
C3—H30.9300C24—C251.427 (2)
C4—C101.413 (2)C24—H240.9300
C4—H40.9300C25—C261.4294 (19)
C5—C61.362 (3)C27—C281.367 (2)
C5—C101.409 (2)C27—C301.423 (2)
C5—H50.9300C28—H280.9300
C6—C71.390 (2)C29—H290.9300
C6—H60.9300C31—C321.487 (2)
C7—C81.359 (2)C32—H32A0.9600
C7—H70.9300C32—H32B0.9600
C8—C91.421 (2)C32—H32C0.9600
N4—O1—H1O98.9 (15)N3—C15—C16122.39 (13)
N8—O2—H2O97.5 (14)C15—C16—H16A109.5
C13—N1—C12114.56 (14)C15—C16—H16B109.5
C13—N2—C14116.63 (13)H16A—C16—H16B109.5
C14—N3—C15130.23 (13)C15—C16—H16C109.5
C14—N3—H3N115.0 (13)H16A—C16—H16C109.5
C15—N3—H3N114.2 (13)H16B—C16—H16C109.5
C15—N4—O1111.06 (12)C18—C17—C25119.44 (14)
C29—N5—C28114.32 (14)C18—C17—C27120.44 (14)
C29—N6—C30116.43 (14)C25—C17—C27120.08 (13)
C30—N7—C31130.34 (13)C17—C18—C19121.52 (16)
C30—N7—H7N115.1 (12)C17—C18—H18119.2
C31—N7—H7N114.1 (13)C19—C18—H18119.2
C31—N8—O2111.40 (12)C20—C19—C18120.04 (15)
C2—C1—C9119.40 (15)C20—C19—H19120.0
C2—C1—C11120.27 (15)C18—C19—H19120.0
C9—C1—C11120.32 (13)C19—C20—C26120.78 (15)
C1—C2—C3121.27 (17)C19—C20—H20119.6
C1—C2—H2119.4C26—C20—H20119.6
C3—C2—H2119.4C22—C21—C26121.77 (15)
C4—C3—C2120.23 (17)C22—C21—H21119.1
C4—C3—H3119.9C26—C21—H21119.1
C2—C3—H3119.9C21—C22—C23119.64 (15)
C3—C4—C10120.85 (17)C21—C22—H22120.2
C3—C4—H4119.6C23—C22—H22120.2
C10—C4—H4119.6C24—C23—C22121.15 (16)
C6—C5—C10121.85 (16)C24—C23—H23119.4
C6—C5—H5119.1C22—C23—H23119.4
C10—C5—H5119.1C23—C24—C25120.88 (14)
C5—C6—C7119.67 (17)C23—C24—H24119.6
C5—C6—H6120.2C25—C24—H24119.6
C7—C6—H6120.2C17—C25—C24122.98 (13)
C8—C7—C6120.99 (17)C17—C25—C26119.11 (13)
C8—C7—H7119.5C24—C25—C26117.90 (13)
C6—C7—H7119.5C21—C26—C20122.28 (14)
C7—C8—C9121.24 (15)C21—C26—C25118.62 (13)
C7—C8—H8119.4C20—C26—C25119.10 (14)
C9—C8—H8119.4C28—C27—C30115.80 (14)
C8—C9—C1123.02 (14)C28—C27—C17120.37 (14)
C8—C9—C10117.73 (14)C30—C27—C17123.83 (13)
C1—C9—C10119.25 (14)N5—C28—C27124.22 (16)
C5—C10—C4122.60 (16)N5—C28—H28117.9
C5—C10—C9118.49 (15)C27—C28—H28117.9
C4—C10—C9118.91 (16)N5—C29—N6128.26 (15)
C12—C11—C14115.04 (14)N5—C29—H29115.9
C12—C11—C1121.42 (14)N6—C29—H29115.9
C14—C11—C1123.54 (13)N6—C30—N7119.35 (13)
N1—C12—C11124.61 (15)N6—C30—C27120.95 (14)
N1—C12—H12117.7N7—C30—C27119.70 (13)
C11—C12—H12117.7N8—C31—N7120.72 (14)
N1—C13—N2127.78 (16)N8—C31—C32116.61 (14)
N1—C13—H13116.1N7—C31—C32122.64 (14)
N2—C13—H13116.1C31—C32—H32A109.5
N2—C14—N3119.78 (12)C31—C32—H32B109.5
N2—C14—C11121.24 (13)H32A—C32—H32B109.5
N3—C14—C11118.97 (13)C31—C32—H32C109.5
N4—C15—N3120.00 (13)H32A—C32—H32C109.5
N4—C15—C16117.57 (13)H32B—C32—H32C109.5
C9—C1—C2—C32.3 (3)C25—C17—C18—C191.0 (2)
C11—C1—C2—C3178.83 (16)C27—C17—C18—C19178.78 (15)
C1—C2—C3—C40.2 (3)C17—C18—C19—C200.5 (3)
C2—C3—C4—C102.1 (3)C18—C19—C20—C261.0 (3)
C10—C5—C6—C70.7 (3)C26—C21—C22—C230.1 (3)
C5—C6—C7—C80.7 (3)C21—C22—C23—C240.9 (3)
C6—C7—C8—C90.8 (3)C22—C23—C24—C250.3 (3)
C7—C8—C9—C1179.74 (15)C18—C17—C25—C24177.09 (14)
C7—C8—C9—C100.5 (2)C27—C17—C25—C240.7 (2)
C2—C1—C9—C8176.77 (15)C18—C17—C25—C262.0 (2)
C11—C1—C9—C82.1 (2)C27—C17—C25—C26179.83 (12)
C2—C1—C9—C103.0 (2)C23—C24—C25—C17179.67 (15)
C11—C1—C9—C10178.15 (13)C23—C24—C25—C261.2 (2)
C6—C5—C10—C4178.42 (16)C22—C21—C26—C20178.07 (16)
C6—C5—C10—C92.0 (2)C22—C21—C26—C251.6 (2)
C3—C4—C10—C5179.07 (17)C19—C20—C26—C21179.77 (16)
C3—C4—C10—C91.3 (3)C19—C20—C26—C250.1 (2)
C8—C9—C10—C51.8 (2)C17—C25—C26—C21178.73 (13)
C1—C9—C10—C5178.41 (14)C24—C25—C26—C212.1 (2)
C8—C9—C10—C4178.57 (15)C17—C25—C26—C201.6 (2)
C1—C9—C10—C41.2 (2)C24—C25—C26—C20177.57 (14)
C2—C1—C11—C1266.0 (2)C18—C17—C27—C2868.1 (2)
C9—C1—C11—C12112.85 (17)C25—C17—C27—C28109.68 (17)
C2—C1—C11—C14113.21 (18)C18—C17—C27—C30112.52 (18)
C9—C1—C11—C1467.9 (2)C25—C17—C27—C3069.7 (2)
C13—N1—C12—C110.3 (2)C29—N5—C28—C270.3 (3)
C14—C11—C12—N13.1 (2)C30—C27—C28—N51.5 (2)
C1—C11—C12—N1177.60 (14)C17—C27—C28—N5177.89 (14)
C12—N1—C13—N21.9 (3)C28—N5—C29—N61.1 (3)
C14—N2—C13—N10.8 (3)C30—N6—C29—N50.9 (3)
C13—N2—C14—N3178.20 (14)C29—N6—C30—N7179.77 (14)
C13—N2—C14—C112.5 (2)C29—N6—C30—C270.6 (2)
C15—N3—C14—N219.0 (2)C31—N7—C30—N614.0 (3)
C15—N3—C14—C11161.64 (14)C31—N7—C30—C27166.31 (15)
C12—C11—C14—N24.2 (2)C28—C27—C30—N61.7 (2)
C1—C11—C14—N2176.50 (14)C17—C27—C30—N6177.71 (14)
C12—C11—C14—N3176.43 (14)C28—C27—C30—N7178.68 (14)
C1—C11—C14—N32.8 (2)C17—C27—C30—N71.9 (2)
O1—N4—C15—N32.1 (2)O2—N8—C31—N71.4 (2)
O1—N4—C15—C16179.69 (13)O2—N8—C31—C32179.46 (14)
C14—N3—C15—N4179.04 (15)C30—N7—C31—N8179.00 (15)
C14—N3—C15—C161.5 (2)C30—N7—C31—C321.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N5i0.86 (2)1.89 (2)2.744 (2)175.4 (19)
O2—H2O···N10.88 (2)1.89 (2)2.762 (2)172.7 (18)
N3—H3N···O10.90 (2)2.064 (19)2.4878 (17)107.5 (15)
N7—H7N···O20.870 (19)2.097 (18)2.5068 (18)108.0 (14)
Symmetry code: (i) x1, y+1, z1.
 

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