The title compound, C
18H
14O
2N
2, 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
CCDC reference: 232167
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.088
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
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
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
C18H14N2O2 | F(000) = 608 |
Mr = 290.31 | Dx = 1.269 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4977 reflections |
a = 12.0073 (11) Å | θ = 2.3–27.9° |
b = 8.4530 (9) Å | µ = 0.08 mm−1 |
c = 15.0167 (15) Å | T = 293 K |
β = 94.188 (8)° | Block, yellow |
V = 1520.1 (3) Å3 | 0.30 × 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 tube | Rint = 0.055 |
Plane graphite monochromator | θmax = 28.3°, θmin = 2.7° |
Detector resolution: 6.67 pixels mm-1 | h = −14→15 |
rotation method scans | k = −11→11 |
13837 measured reflections | l = −20→20 |
3713 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.088 | All 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 parameters | Δρmax = 0.11 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
H91 | 0.1390 (15) | −0.0134 (18) | 0.2008 (10) | 0.065 (5)* | |
H141 | 0.3116 (14) | 0.205 (2) | −0.1472 (10) | 0.068 (5)* | |
H21 | 0.1133 (15) | 0.2693 (18) | −0.0679 (11) | 0.069 (5)* | |
H151 | 0.3589 (16) | 0.311 (2) | −0.2801 (13) | 0.088 (6)* | |
H31 | −0.0658 (15) | 0.3700 (19) | −0.0817 (11) | 0.073 (5)* | |
H61 | −0.2365 (18) | 0.143 (2) | 0.1550 (12) | 0.081 (6)* | |
H81 | 0.0113 (17) | −0.084 (2) | 0.3007 (14) | 0.102 (7)* | |
H181 | 0.3969 (16) | 0.616 (2) | −0.0147 (13) | 0.088 (6)* | |
H41 | −0.1926 (15) | 0.2905 (18) | 0.0198 (10) | 0.067 (5)* | |
H71 | −0.1784 (18) | −0.013 (2) | 0.2764 (13) | 0.089 (6)* | |
H1 | 0.2198 (14) | −0.007 (2) | 0.0737 (11) | 0.072 (5)* | |
H161 | 0.4340 (19) | 0.573 (2) | −0.2852 (15) | 0.108 (7)* | |
H171 | 0.4542 (18) | 0.728 (3) | −0.1510 (14) | 0.113 (7)* | |
H2 | 0.459 (2) | −0.108 (2) | 0.0243 (13) | 0.100 (7)* | |
N1 | 0.21264 (11) | 0.09477 (16) | 0.05841 (9) | 0.0530 (3) | |
N2 | 0.39469 (11) | 0.08814 (14) | 0.01221 (9) | 0.0542 (3) | |
O1 | 0.38655 (11) | −0.07456 (13) | 0.03553 (8) | 0.0663 (3) | |
C1 | 0.10231 (13) | 0.15462 (16) | 0.04892 (10) | 0.0456 (4) | |
C10 | 0.02810 (13) | 0.10920 (15) | 0.11385 (10) | 0.0462 (4) | |
O2 | 0.28815 (10) | 0.42290 (12) | 0.07447 (8) | 0.0658 (3) | |
C12 | 0.31098 (12) | 0.33849 (17) | 0.01292 (10) | 0.0479 (4) | |
C5 | −0.08479 (14) | 0.15910 (17) | 0.10137 (10) | 0.0520 (4) | |
C13 | 0.34937 (13) | 0.39999 (17) | −0.07136 (10) | 0.0490 (4) | |
C11 | 0.30295 (13) | 0.16120 (16) | 0.02488 (9) | 0.0469 (4) | |
C9 | 0.06046 (16) | 0.01784 (19) | 0.19002 (11) | 0.0590 (4) | |
C4 | −0.11794 (15) | 0.25776 (19) | 0.02803 (12) | 0.0594 (4) | |
C2 | 0.06596 (14) | 0.24696 (18) | −0.02170 (11) | 0.0552 (4) | |
C6 | −0.16088 (18) | 0.1091 (2) | 0.16332 (13) | 0.0673 (5) | |
C18 | 0.39009 (14) | 0.5545 (2) | −0.07290 (13) | 0.0598 (4) | |
C7 | −0.1269 (2) | 0.0187 (2) | 0.23417 (14) | 0.0752 (6) | |
C14 | 0.34136 (15) | 0.3115 (2) | −0.14907 (11) | 0.0623 (5) | |
C3 | −0.04432 (15) | 0.3017 (2) | −0.03068 (12) | 0.0603 (4) | |
C8 | −0.01551 (18) | −0.0273 (2) | 0.24841 (14) | 0.0707 (5) | |
C15 | 0.37249 (19) | 0.3775 (3) | −0.22785 (14) | 0.0830 (6) | |
C17 | 0.42236 (18) | 0.6171 (3) | −0.15090 (16) | 0.0807 (6) | |
C16 | 0.41376 (19) | 0.5303 (3) | −0.22797 (17) | 0.0915 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0408 (9) | 0.0480 (8) | 0.0709 (9) | 0.0069 (6) | 0.0086 (6) | 0.0053 (6) |
N2 | 0.0469 (9) | 0.0425 (7) | 0.0742 (9) | 0.0050 (6) | 0.0117 (6) | −0.0028 (6) |
O1 | 0.0505 (9) | 0.0461 (6) | 0.1039 (10) | 0.0078 (5) | 0.0168 (7) | 0.0044 (6) |
C1 | 0.0381 (10) | 0.0428 (8) | 0.0558 (9) | 0.0030 (6) | 0.0027 (7) | −0.0052 (7) |
C10 | 0.0429 (10) | 0.0413 (8) | 0.0546 (9) | 0.0001 (6) | 0.0041 (7) | −0.0038 (6) |
O2 | 0.0729 (9) | 0.0560 (6) | 0.0708 (7) | 0.0013 (5) | 0.0201 (6) | −0.0159 (6) |
C12 | 0.0361 (10) | 0.0488 (8) | 0.0589 (10) | 0.0040 (6) | 0.0034 (7) | −0.0073 (8) |
C5 | 0.0433 (11) | 0.0495 (8) | 0.0635 (10) | −0.0015 (7) | 0.0064 (7) | −0.0065 (7) |
C13 | 0.0363 (10) | 0.0514 (9) | 0.0596 (10) | 0.0055 (6) | 0.0045 (7) | −0.0014 (7) |
C11 | 0.0394 (10) | 0.0469 (8) | 0.0547 (9) | 0.0032 (7) | 0.0054 (7) | −0.0044 (7) |
C9 | 0.0533 (13) | 0.0574 (10) | 0.0663 (11) | 0.0008 (8) | 0.0040 (9) | 0.0048 (8) |
C4 | 0.0391 (12) | 0.0563 (10) | 0.0821 (12) | 0.0051 (8) | −0.0002 (9) | −0.0019 (9) |
C2 | 0.0471 (12) | 0.0599 (10) | 0.0587 (10) | −0.0024 (8) | 0.0047 (8) | 0.0034 (8) |
C6 | 0.0465 (13) | 0.0760 (12) | 0.0805 (14) | −0.0036 (9) | 0.0132 (10) | −0.0066 (10) |
C18 | 0.0442 (11) | 0.0569 (10) | 0.0785 (13) | 0.0012 (7) | 0.0047 (8) | 0.0058 (9) |
C7 | 0.0663 (16) | 0.0882 (14) | 0.0737 (14) | −0.0156 (11) | 0.0221 (11) | −0.0010 (11) |
C14 | 0.0584 (13) | 0.0692 (12) | 0.0595 (11) | 0.0038 (9) | 0.0056 (8) | −0.0048 (9) |
C3 | 0.0500 (12) | 0.0583 (10) | 0.0713 (12) | 0.0038 (7) | −0.0049 (9) | 0.0104 (9) |
C8 | 0.0722 (17) | 0.0727 (12) | 0.0678 (12) | −0.0070 (10) | 0.0099 (10) | 0.0100 (10) |
C15 | 0.0769 (17) | 0.1135 (18) | 0.0590 (13) | 0.0133 (12) | 0.0079 (10) | −0.0017 (13) |
C17 | 0.0636 (15) | 0.0823 (15) | 0.0971 (17) | −0.0022 (10) | 0.0132 (11) | 0.0239 (13) |
C16 | 0.0747 (17) | 0.120 (2) | 0.0811 (17) | 0.0075 (13) | 0.0179 (12) | 0.0366 (15) |
Geometric parameters (Å, º) top
N1—C11 | 1.3507 (19) | C4—C3 | 1.346 (2) |
N1—C1 | 1.4156 (19) | C4—H41 | 0.938 (17) |
N1—H1 | 0.889 (18) | C2—C3 | 1.400 (2) |
N2—C11 | 1.2890 (18) | C2—H21 | 0.947 (17) |
N2—O1 | 1.4243 (15) | C6—C7 | 1.349 (3) |
O1—H2 | 0.94 (2) | C6—H61 | 0.95 (2) |
C1—C2 | 1.363 (2) | C18—C17 | 1.367 (3) |
C1—C10 | 1.421 (2) | C18—H181 | 1.013 (19) |
C10—C9 | 1.411 (2) | C7—C8 | 1.395 (3) |
C10—C5 | 1.419 (2) | C7—H71 | 0.96 (2) |
O2—C12 | 1.2147 (17) | C14—C15 | 1.384 (3) |
C12—C13 | 1.473 (2) | C14—H141 | 0.966 (16) |
C12—C11 | 1.513 (2) | C3—H31 | 0.979 (17) |
C5—C6 | 1.415 (2) | C8—H81 | 0.96 (2) |
C5—C4 | 1.415 (2) | C15—C16 | 1.383 (3) |
C13—C14 | 1.383 (2) | C15—H151 | 0.968 (19) |
C13—C18 | 1.395 (2) | C17—C16 | 1.368 (3) |
C9—C8 | 1.365 (3) | C17—H171 | 1.01 (2) |
C9—H91 | 0.981 (18) | C16—H161 | 0.98 (2) |
| | | |
C11—N1—C1 | 125.79 (14) | C1—C2—H21 | 120.6 (11) |
C11—N1—H1 | 115.6 (11) | C3—C2—H21 | 118.5 (11) |
C1—N1—H1 | 116.2 (11) | C7—C6—C5 | 121.0 (2) |
C11—N2—O1 | 110.59 (12) | C7—C6—H61 | 120.2 (11) |
N2—O1—H2 | 99.6 (12) | C5—C6—H61 | 118.8 (11) |
C2—C1—N1 | 121.82 (14) | C17—C18—C13 | 119.89 (19) |
C2—C1—C10 | 120.50 (14) | C17—C18—H181 | 122.1 (11) |
N1—C1—C10 | 117.62 (13) | C13—C18—H181 | 118.0 (10) |
C9—C10—C5 | 118.27 (15) | C6—C7—C8 | 120.7 (2) |
C9—C10—C1 | 123.70 (14) | C6—C7—H71 | 120.7 (12) |
C5—C10—C1 | 118.03 (14) | C8—C7—H71 | 118.7 (12) |
O2—C12—C13 | 123.28 (14) | C13—C14—C15 | 119.8 (2) |
O2—C12—C11 | 118.13 (14) | C13—C14—H141 | 118.7 (10) |
C13—C12—C11 | 118.57 (12) | C15—C14—H141 | 121.5 (10) |
C6—C5—C4 | 121.94 (16) | C4—C3—C2 | 120.51 (17) |
C6—C5—C10 | 118.74 (16) | C4—C3—H31 | 121.8 (10) |
C4—C5—C10 | 119.32 (15) | C2—C3—H31 | 117.7 (10) |
C14—C13—C18 | 119.67 (16) | C9—C8—C7 | 120.2 (2) |
C14—C13—C12 | 121.81 (14) | C9—C8—H81 | 117.9 (13) |
C18—C13—C12 | 118.46 (14) | C7—C8—H81 | 121.8 (13) |
N2—C11—N1 | 125.01 (14) | C16—C15—C14 | 119.8 (2) |
N2—C11—C12 | 113.23 (13) | C16—C15—H151 | 125.2 (11) |
N1—C11—C12 | 121.05 (13) | C14—C15—H151 | 114.9 (11) |
C8—C9—C10 | 121.08 (19) | C18—C17—C16 | 120.5 (2) |
C8—C9—H91 | 119.8 (10) | C18—C17—H171 | 119.4 (12) |
C10—C9—H91 | 119.1 (10) | C16—C17—H171 | 120.1 (12) |
C3—C4—C5 | 120.78 (16) | C17—C16—C15 | 120.3 (2) |
C3—C4—H41 | 120.0 (10) | C17—C16—H161 | 122.6 (12) |
C5—C4—H41 | 119.2 (10) | C15—C16—H161 | 117.1 (12) |
C1—C2—C3 | 120.75 (16) | | |
| | | |
C11—N1—C1—C2 | 26.6 (2) | C5—C10—C9—C8 | 2.7 (2) |
C11—N1—C1—C10 | −156.23 (14) | C1—C10—C9—C8 | −177.51 (15) |
C2—C1—C10—C9 | −178.07 (14) | C6—C5—C4—C3 | −179.00 (16) |
N1—C1—C10—C9 | 4.7 (2) | C10—C5—C4—C3 | 1.4 (2) |
C2—C1—C10—C5 | 1.7 (2) | N1—C1—C2—C3 | 178.50 (14) |
N1—C1—C10—C5 | −175.49 (13) | C10—C1—C2—C3 | 1.4 (2) |
C9—C10—C5—C6 | −2.9 (2) | C4—C5—C6—C7 | −178.15 (17) |
C1—C10—C5—C6 | 177.28 (14) | C10—C5—C6—C7 | 1.5 (2) |
C9—C10—C5—C4 | 176.70 (15) | C14—C13—C18—C17 | −0.4 (2) |
C1—C10—C5—C4 | −3.1 (2) | C12—C13—C18—C17 | −177.49 (16) |
O2—C12—C13—C14 | −159.27 (16) | C5—C6—C7—C8 | 0.3 (3) |
C11—C12—C13—C14 | 22.7 (2) | C18—C13—C14—C15 | −0.8 (2) |
O2—C12—C13—C18 | 17.8 (2) | C12—C13—C14—C15 | 176.26 (17) |
C11—C12—C13—C18 | −160.19 (14) | C5—C4—C3—C2 | 1.8 (3) |
O1—N2—C11—N1 | 2.1 (2) | C1—C2—C3—C4 | −3.2 (2) |
O1—N2—C11—C12 | 172.49 (11) | C10—C9—C8—C7 | −0.9 (3) |
C1—N1—C11—N2 | −160.03 (15) | C6—C7—C8—C9 | −0.6 (3) |
C1—N1—C11—C12 | 30.2 (2) | C13—C14—C15—C16 | 1.4 (3) |
O2—C12—C11—N2 | −123.78 (16) | C13—C18—C17—C16 | 0.8 (3) |
C13—C12—C11—N2 | 54.32 (19) | C18—C17—C16—C15 | −0.2 (3) |
O2—C12—C11—N1 | 47.1 (2) | C14—C15—C16—C17 | −1.0 (3) |
C13—C12—C11—N1 | −134.83 (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—O1 | 1.424 (2) | 1.403 (2)/1.396 (2) | 1.423 (3)/1.396 (3) | 1.429 (4) | 1.417 (1) |
N2—C11 | 1.289 (2) | 1.281 (2)/1.281 (2) | 1.290 (3)/1.282 (3) | 1.241 (6) | 1.290 (1) |
C11—C12 | 1.513 (2) | 1.477 (3)/1.473 (3) | 1.489 (3) | 1.551 (7) | 1.510 (1) |
C12—C11—N2 | 113.2 (1) | 115.2 (2)/115.0 (2) | 116.6 (2)/115.0 (2) | 118.3 (5) | 114.3 (1) |
C11—N2—O1 | 110.6 (1) | 112.4 (1)/112.2 (1) | 109.4 (2)/111.5 (2) | 112.2 (4) | 110.7 (1) |