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The title compound, C18H14O2N2, consists of an amino­naphthalene group and a 2-phenyl-1,2-ethanedione 1-oxime group. Intermolecular O—H...N and O—H...O hydrogen bonds [O...N = 2.775 (2) Å and O...O = 3.252 (2) Å], and π–π interactions are highly effective in forming chains, thereby stabilizing the crystal structure. The oxime group has the E configuration.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803028617/ci6316sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803028617/ci6316Isup2.hkl
Contains datablock I

CCDC reference: 232167

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.088
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

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Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 44 Perc.
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 0 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 0 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-RED (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 (Farrugia, 1999).

N-Hydroxy-N'-(1-naphthyl)-2-phenylacetamidin-2-one top
Crystal data top
C18H14N2O2F(000) = 608
Mr = 290.31Dx = 1.269 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4977 reflections
a = 12.0073 (11) Åθ = 2.3–27.9°
b = 8.4530 (9) ŵ = 0.08 mm1
c = 15.0167 (15) ÅT = 293 K
β = 94.188 (8)°Block, yellow
V = 1520.1 (3) Å30.30 × 0.26 × 0.19 mm
Z = 4
Data collection top
Stoe IPDS-II
diffractometer
1641 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.055
Plane graphite monochromatorθmax = 28.3°, θmin = 2.7°
Detector resolution: 6.67 pixels mm-1h = 1415
rotation method scansk = 1111
13837 measured reflectionsl = 2020
3713 independent 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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088All H-atom parameters refined
S = 0.86 w = 1/[σ2(Fo2) + (0.0423P)2]
where P = (Fo2 + 2Fc2)/3
3713 reflections(Δ/σ)max < 0.001
255 parametersΔρmax = 0.11 e Å3
0 restraintsΔρmin = 0.20 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
H910.1390 (15)0.0134 (18)0.2008 (10)0.065 (5)*
H1410.3116 (14)0.205 (2)0.1472 (10)0.068 (5)*
H210.1133 (15)0.2693 (18)0.0679 (11)0.069 (5)*
H1510.3589 (16)0.311 (2)0.2801 (13)0.088 (6)*
H310.0658 (15)0.3700 (19)0.0817 (11)0.073 (5)*
H610.2365 (18)0.143 (2)0.1550 (12)0.081 (6)*
H810.0113 (17)0.084 (2)0.3007 (14)0.102 (7)*
H1810.3969 (16)0.616 (2)0.0147 (13)0.088 (6)*
H410.1926 (15)0.2905 (18)0.0198 (10)0.067 (5)*
H710.1784 (18)0.013 (2)0.2764 (13)0.089 (6)*
H10.2198 (14)0.007 (2)0.0737 (11)0.072 (5)*
H1610.4340 (19)0.573 (2)0.2852 (15)0.108 (7)*
H1710.4542 (18)0.728 (3)0.1510 (14)0.113 (7)*
H20.459 (2)0.108 (2)0.0243 (13)0.100 (7)*
N10.21264 (11)0.09477 (16)0.05841 (9)0.0530 (3)
N20.39469 (11)0.08814 (14)0.01221 (9)0.0542 (3)
O10.38655 (11)0.07456 (13)0.03553 (8)0.0663 (3)
C10.10231 (13)0.15462 (16)0.04892 (10)0.0456 (4)
C100.02810 (13)0.10920 (15)0.11385 (10)0.0462 (4)
O20.28815 (10)0.42290 (12)0.07447 (8)0.0658 (3)
C120.31098 (12)0.33849 (17)0.01292 (10)0.0479 (4)
C50.08479 (14)0.15910 (17)0.10137 (10)0.0520 (4)
C130.34937 (13)0.39999 (17)0.07136 (10)0.0490 (4)
C110.30295 (13)0.16120 (16)0.02488 (9)0.0469 (4)
C90.06046 (16)0.01784 (19)0.19002 (11)0.0590 (4)
C40.11794 (15)0.25776 (19)0.02803 (12)0.0594 (4)
C20.06596 (14)0.24696 (18)0.02170 (11)0.0552 (4)
C60.16088 (18)0.1091 (2)0.16332 (13)0.0673 (5)
C180.39009 (14)0.5545 (2)0.07290 (13)0.0598 (4)
C70.1269 (2)0.0187 (2)0.23417 (14)0.0752 (6)
C140.34136 (15)0.3115 (2)0.14907 (11)0.0623 (5)
C30.04432 (15)0.3017 (2)0.03068 (12)0.0603 (4)
C80.01551 (18)0.0273 (2)0.24841 (14)0.0707 (5)
C150.37249 (19)0.3775 (3)0.22785 (14)0.0830 (6)
C170.42236 (18)0.6171 (3)0.15090 (16)0.0807 (6)
C160.41376 (19)0.5303 (3)0.22797 (17)0.0915 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0408 (9)0.0480 (8)0.0709 (9)0.0069 (6)0.0086 (6)0.0053 (6)
N20.0469 (9)0.0425 (7)0.0742 (9)0.0050 (6)0.0117 (6)0.0028 (6)
O10.0505 (9)0.0461 (6)0.1039 (10)0.0078 (5)0.0168 (7)0.0044 (6)
C10.0381 (10)0.0428 (8)0.0558 (9)0.0030 (6)0.0027 (7)0.0052 (7)
C100.0429 (10)0.0413 (8)0.0546 (9)0.0001 (6)0.0041 (7)0.0038 (6)
O20.0729 (9)0.0560 (6)0.0708 (7)0.0013 (5)0.0201 (6)0.0159 (6)
C120.0361 (10)0.0488 (8)0.0589 (10)0.0040 (6)0.0034 (7)0.0073 (8)
C50.0433 (11)0.0495 (8)0.0635 (10)0.0015 (7)0.0064 (7)0.0065 (7)
C130.0363 (10)0.0514 (9)0.0596 (10)0.0055 (6)0.0045 (7)0.0014 (7)
C110.0394 (10)0.0469 (8)0.0547 (9)0.0032 (7)0.0054 (7)0.0044 (7)
C90.0533 (13)0.0574 (10)0.0663 (11)0.0008 (8)0.0040 (9)0.0048 (8)
C40.0391 (12)0.0563 (10)0.0821 (12)0.0051 (8)0.0002 (9)0.0019 (9)
C20.0471 (12)0.0599 (10)0.0587 (10)0.0024 (8)0.0047 (8)0.0034 (8)
C60.0465 (13)0.0760 (12)0.0805 (14)0.0036 (9)0.0132 (10)0.0066 (10)
C180.0442 (11)0.0569 (10)0.0785 (13)0.0012 (7)0.0047 (8)0.0058 (9)
C70.0663 (16)0.0882 (14)0.0737 (14)0.0156 (11)0.0221 (11)0.0010 (11)
C140.0584 (13)0.0692 (12)0.0595 (11)0.0038 (9)0.0056 (8)0.0048 (9)
C30.0500 (12)0.0583 (10)0.0713 (12)0.0038 (7)0.0049 (9)0.0104 (9)
C80.0722 (17)0.0727 (12)0.0678 (12)0.0070 (10)0.0099 (10)0.0100 (10)
C150.0769 (17)0.1135 (18)0.0590 (13)0.0133 (12)0.0079 (10)0.0017 (13)
C170.0636 (15)0.0823 (15)0.0971 (17)0.0022 (10)0.0132 (11)0.0239 (13)
C160.0747 (17)0.120 (2)0.0811 (17)0.0075 (13)0.0179 (12)0.0366 (15)
Geometric parameters (Å, º) top
N1—C111.3507 (19)C4—C31.346 (2)
N1—C11.4156 (19)C4—H410.938 (17)
N1—H10.889 (18)C2—C31.400 (2)
N2—C111.2890 (18)C2—H210.947 (17)
N2—O11.4243 (15)C6—C71.349 (3)
O1—H20.94 (2)C6—H610.95 (2)
C1—C21.363 (2)C18—C171.367 (3)
C1—C101.421 (2)C18—H1811.013 (19)
C10—C91.411 (2)C7—C81.395 (3)
C10—C51.419 (2)C7—H710.96 (2)
O2—C121.2147 (17)C14—C151.384 (3)
C12—C131.473 (2)C14—H1410.966 (16)
C12—C111.513 (2)C3—H310.979 (17)
C5—C61.415 (2)C8—H810.96 (2)
C5—C41.415 (2)C15—C161.383 (3)
C13—C141.383 (2)C15—H1510.968 (19)
C13—C181.395 (2)C17—C161.368 (3)
C9—C81.365 (3)C17—H1711.01 (2)
C9—H910.981 (18)C16—H1610.98 (2)
C11—N1—C1125.79 (14)C1—C2—H21120.6 (11)
C11—N1—H1115.6 (11)C3—C2—H21118.5 (11)
C1—N1—H1116.2 (11)C7—C6—C5121.0 (2)
C11—N2—O1110.59 (12)C7—C6—H61120.2 (11)
N2—O1—H299.6 (12)C5—C6—H61118.8 (11)
C2—C1—N1121.82 (14)C17—C18—C13119.89 (19)
C2—C1—C10120.50 (14)C17—C18—H181122.1 (11)
N1—C1—C10117.62 (13)C13—C18—H181118.0 (10)
C9—C10—C5118.27 (15)C6—C7—C8120.7 (2)
C9—C10—C1123.70 (14)C6—C7—H71120.7 (12)
C5—C10—C1118.03 (14)C8—C7—H71118.7 (12)
O2—C12—C13123.28 (14)C13—C14—C15119.8 (2)
O2—C12—C11118.13 (14)C13—C14—H141118.7 (10)
C13—C12—C11118.57 (12)C15—C14—H141121.5 (10)
C6—C5—C4121.94 (16)C4—C3—C2120.51 (17)
C6—C5—C10118.74 (16)C4—C3—H31121.8 (10)
C4—C5—C10119.32 (15)C2—C3—H31117.7 (10)
C14—C13—C18119.67 (16)C9—C8—C7120.2 (2)
C14—C13—C12121.81 (14)C9—C8—H81117.9 (13)
C18—C13—C12118.46 (14)C7—C8—H81121.8 (13)
N2—C11—N1125.01 (14)C16—C15—C14119.8 (2)
N2—C11—C12113.23 (13)C16—C15—H151125.2 (11)
N1—C11—C12121.05 (13)C14—C15—H151114.9 (11)
C8—C9—C10121.08 (19)C18—C17—C16120.5 (2)
C8—C9—H91119.8 (10)C18—C17—H171119.4 (12)
C10—C9—H91119.1 (10)C16—C17—H171120.1 (12)
C3—C4—C5120.78 (16)C17—C16—C15120.3 (2)
C3—C4—H41120.0 (10)C17—C16—H161122.6 (12)
C5—C4—H41119.2 (10)C15—C16—H161117.1 (12)
C1—C2—C3120.75 (16)
C11—N1—C1—C226.6 (2)C5—C10—C9—C82.7 (2)
C11—N1—C1—C10156.23 (14)C1—C10—C9—C8177.51 (15)
C2—C1—C10—C9178.07 (14)C6—C5—C4—C3179.00 (16)
N1—C1—C10—C94.7 (2)C10—C5—C4—C31.4 (2)
C2—C1—C10—C51.7 (2)N1—C1—C2—C3178.50 (14)
N1—C1—C10—C5175.49 (13)C10—C1—C2—C31.4 (2)
C9—C10—C5—C62.9 (2)C4—C5—C6—C7178.15 (17)
C1—C10—C5—C6177.28 (14)C10—C5—C6—C71.5 (2)
C9—C10—C5—C4176.70 (15)C14—C13—C18—C170.4 (2)
C1—C10—C5—C43.1 (2)C12—C13—C18—C17177.49 (16)
O2—C12—C13—C14159.27 (16)C5—C6—C7—C80.3 (3)
C11—C12—C13—C1422.7 (2)C18—C13—C14—C150.8 (2)
O2—C12—C13—C1817.8 (2)C12—C13—C14—C15176.26 (17)
C11—C12—C13—C18160.19 (14)C5—C4—C3—C21.8 (3)
O1—N2—C11—N12.1 (2)C1—C2—C3—C43.2 (2)
O1—N2—C11—C12172.49 (11)C10—C9—C8—C70.9 (3)
C1—N1—C11—N2160.03 (15)C6—C7—C8—C90.6 (3)
C1—N1—C11—C1230.2 (2)C13—C14—C15—C161.4 (3)
O2—C12—C11—N2123.78 (16)C13—C18—C17—C160.8 (3)
C13—C12—C11—N254.32 (19)C18—C17—C16—C150.2 (3)
O2—C12—C11—N147.1 (2)C14—C15—C16—C171.0 (3)
C13—C12—C11—N1134.83 (15)
Comparison of the bond lengths and angles (Å, °) in the oxime moiety of (I) with the corresponding values in the related compounds (II)–(V). top
(I)(II)(III)(IV)(V)
N2—O11.424 (2)1.403 (2)/1.396 (2)1.423 (3)/1.396 (3)1.429 (4)1.417 (1)
N2—C111.289 (2)1.281 (2)/1.281 (2)1.290 (3)/1.282 (3)1.241 (6)1.290 (1)
C11—C121.513 (2)1.477 (3)/1.473 (3)1.489 (3)1.551 (7)1.510 (1)
C12—C11—N2113.2 (1)115.2 (2)/115.0 (2)116.6 (2)/115.0 (2)118.3 (5)114.3 (1)
C11—N2—O1110.6 (1)112.4 (1)/112.2 (1)109.4 (2)/111.5 (2)112.2 (4)110.7 (1)
 

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