Literature DB >> 24454065

N'-[(E)-Benzyl-idene]-2-(6-meth-oxy-naphthalen-2-yl)propano-hydrazide.

Joel T Mague1, Mehmet Akkurt2, Shaaban K Mohamed3, Mahmoud A A El-Remaily4, Mustafa R Albayati5.   

Abstract

The title mol-ecule, C21H20N2O2, exists in the solid state in the 'extended' form. The crystal packing consists of ribbons of mol-ecules extending parallel to c and associated via N-H⋯O and weak C-H⋯O hydrogen bonds. C-H⋯π inter-actions are also present.

Entities:  

Year:  2013        PMID： 24454065      PMCID： PMC3884289          DOI： 10.1107/S1600536813026986

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For general clinical use of nonsteroidal anti-inflammatory drugs (NSAIDs) and Naproxen®, see: Merlet et al. (2013 ▶); Khanna et al. (2006 ▶); Bhaduri et al. (1995 ▶); Dharmani et al. (2004 ▶). For common side effects of NSAIDs, see: Neeraj et al. (2010 ▶); Asif (2009 ▶); Parmeshwari et al. (2009 ▶).

Experimental

Crystal data

C21H20N2O2 M = 332.39 Orthorhombic, a = 10.3754 (17) Å b = 32.519 (5) Å c = 5.0615 (8) Å V = 1707.7 (5) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 150 K 0.15 × 0.11 × 0.11 mm

Data collection

Bruker SMART APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.73, T max = 0.99 28152 measured reflections 4230 independent reflections 3882 reflections with I > 2σ(I) R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.052 wR(F 2) = 0.128 S = 1.10 4230 reflections 232 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.34 e Å−3 Δρmin = −0.26 e Å−3 Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813026986/sj5356sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813026986/sj5356Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813026986/sj5356Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C21H20N2O2F(000) = 704
Mr = 332.39Dx = 1.293 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 9954 reflections
a = 10.3754 (17) Åθ = 2.3–28.2°
b = 32.519 (5) ŵ = 0.08 mm−1
c = 5.0615 (8) ÅT = 150 K
V = 1707.7 (5) Å3Block, clear colourless
Z = 40.15 × 0.11 × 0.11 mm
Bruker SMART APEX CCD diffractometer4230 independent reflections
Radiation source: fine-focus sealed tube3882 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
Detector resolution: 8.3660 pixels mm-1θmax = 28.3°, θmin = 2.1°
φ and ω scansh = −13→13
Absorption correction: multi-scan SADABS (Bruker, 2013)k = −43→42
Tmin = 0.73, Tmax = 0.99l = −6→6
28152 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.128w = 1/[Σ2(Fo2) + (0.0416P)2 + 1.3067P] where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
4230 reflectionsΔρmax = 0.34 e Å−3
232 parametersΔρmin = −0.26 e Å−3
0 restraints
Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = -30.00 and 210.00°. The scan time was 25 sec/frame.
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.
xyzUiso*/Ueq
O10.8923 (2)0.05817 (7)1.2997 (5)0.0341 (7)
O21.0001 (3)0.28050 (6)0.4958 (4)0.0327 (7)
N10.9781 (2)0.29446 (7)0.0582 (5)0.0212 (7)
N20.9700 (2)0.33651 (7)0.0988 (5)0.0217 (6)
C10.7617 (3)0.05673 (11)1.3868 (7)0.0360 (10)
C20.9231 (3)0.08584 (8)1.1061 (6)0.0251 (8)
C30.8391 (3)0.11238 (8)0.9855 (6)0.0236 (8)
C40.8842 (3)0.13987 (8)0.7876 (6)0.0206 (8)
C50.8006 (3)0.16752 (9)0.6535 (6)0.0233 (8)
C60.8471 (3)0.19367 (8)0.4643 (6)0.0234 (8)
C70.9800 (3)0.19449 (8)0.3953 (6)0.0206 (7)
C81.0616 (3)0.16783 (8)0.5222 (6)0.0222 (7)
C91.0170 (3)0.13986 (8)0.7169 (6)0.0213 (7)
C101.1001 (3)0.11197 (9)0.8480 (6)0.0255 (8)
C111.0553 (3)0.08558 (9)1.0365 (6)0.0270 (8)
C121.0243 (3)0.22433 (8)0.1836 (6)0.0216 (7)
C131.1682 (3)0.22119 (9)0.1119 (7)0.0282 (8)
C140.9980 (3)0.26884 (8)0.2669 (5)0.0203 (7)
C150.9435 (3)0.35759 (8)−0.1088 (6)0.0222 (8)
C160.9384 (3)0.40269 (8)−0.0976 (6)0.0222 (7)
C170.9991 (3)0.42472 (9)0.1062 (6)0.0261 (8)
C180.9965 (3)0.46725 (9)0.1063 (7)0.0307 (9)
C190.9334 (3)0.48871 (9)−0.0913 (7)0.0316 (9)
C200.8714 (3)0.46720 (10)−0.2899 (7)0.0316 (9)
C210.8748 (3)0.42453 (10)−0.2946 (7)0.0286 (9)
H10.976 (3)0.2849 (10)−0.117 (7)0.025 (8)*
H1A0.735400.084001.448800.0540*
H1B0.753700.036901.531700.0540*
H1C0.706100.048301.239900.0540*
H30.750700.112401.034100.0280*
H50.711400.167900.695700.0280*
H60.789200.211700.376800.0280*
H81.150600.168100.478400.0270*
H101.189000.111600.803600.0310*
H111.112800.067101.121100.0320*
H120.973200.218700.020000.0260*
H13A1.220500.227100.268600.0420*
H13B1.188400.24110−0.027100.0420*
H13C1.187200.193400.048500.0420*
H150.927100.34390−0.271100.0270*
H171.041900.410400.244200.0310*
H181.038700.481900.243700.0370*
H190.932600.51790−0.090500.0380*
H200.826200.48170−0.423900.0380*
H210.833200.41010−0.433800.0340*
U11U22U33U12U13U23
O10.0352 (12)0.0320 (12)0.0351 (12)0.0008 (10)0.0024 (10)0.0129 (10)
O20.0526 (15)0.0248 (10)0.0207 (10)−0.0008 (10)0.0018 (10)−0.0023 (8)
N10.0266 (12)0.0207 (11)0.0162 (11)−0.0018 (9)−0.0001 (9)−0.0013 (9)
N20.0218 (11)0.0211 (11)0.0223 (11)−0.0016 (9)−0.0007 (10)−0.0015 (9)
C10.0376 (17)0.0389 (18)0.0314 (17)−0.0073 (14)0.0031 (15)0.0077 (15)
C20.0324 (15)0.0198 (13)0.0230 (13)−0.0012 (11)0.0018 (12)0.0017 (11)
C30.0209 (13)0.0216 (13)0.0283 (15)−0.0007 (10)0.0017 (11)0.0002 (11)
C40.0220 (13)0.0177 (13)0.0220 (13)0.0001 (10)0.0000 (11)−0.0012 (10)
C50.0176 (12)0.0234 (13)0.0290 (16)0.0029 (10)0.0003 (11)0.0017 (11)
C60.0217 (13)0.0218 (13)0.0267 (15)0.0039 (10)−0.0012 (11)0.0020 (11)
C70.0223 (12)0.0176 (12)0.0218 (12)−0.0002 (9)0.0028 (11)−0.0017 (10)
C80.0179 (12)0.0245 (13)0.0242 (13)0.0000 (10)0.0020 (11)−0.0023 (11)
C90.0215 (13)0.0197 (12)0.0227 (13)0.0011 (10)−0.0004 (11)−0.0017 (10)
C100.0200 (13)0.0293 (15)0.0271 (16)0.0055 (11)0.0002 (12)0.0004 (11)
C110.0296 (15)0.0272 (14)0.0243 (15)0.0073 (11)−0.0042 (12)0.0033 (11)
C120.0228 (13)0.0206 (12)0.0213 (13)−0.0018 (10)0.0009 (11)−0.0015 (10)
C130.0259 (14)0.0268 (14)0.0319 (16)−0.0001 (11)0.0069 (13)0.0007 (13)
C140.0208 (13)0.0236 (13)0.0164 (12)−0.0027 (10)0.0034 (10)−0.0014 (10)
C150.0203 (12)0.0257 (14)0.0205 (13)−0.0023 (10)0.0002 (11)−0.0021 (11)
C160.0183 (12)0.0242 (13)0.0241 (13)−0.0002 (10)0.0025 (11)0.0009 (11)
C170.0247 (14)0.0271 (14)0.0265 (13)0.0003 (11)−0.0023 (12)0.0003 (12)
C180.0335 (16)0.0269 (15)0.0316 (15)−0.0025 (12)0.0001 (14)−0.0045 (12)
C190.0348 (17)0.0204 (14)0.0397 (18)0.0039 (11)0.0070 (15)0.0009 (13)
C200.0292 (16)0.0324 (17)0.0333 (16)0.0065 (12)−0.0008 (13)0.0066 (13)
C210.0251 (14)0.0320 (16)0.0286 (15)−0.0002 (11)−0.0035 (12)0.0013 (13)
O1—C11.426 (4)C17—C181.383 (4)
O1—C21.368 (4)C18—C191.384 (5)
O2—C141.219 (3)C19—C201.383 (5)
N1—N21.385 (3)C20—C211.388 (5)
N1—C141.361 (4)C1—H1A0.9800
N2—C151.284 (4)C1—H1B0.9800
N1—H10.94 (3)C1—H1C0.9800
C2—C111.416 (4)C3—H30.9500
C2—C31.370 (4)C5—H50.9500
C3—C41.422 (4)C6—H60.9500
C4—C91.424 (4)C8—H80.9500
C4—C51.422 (4)C10—H100.9500
C5—C61.369 (4)C11—H110.9500
C6—C71.423 (4)C12—H121.0000
C7—C121.517 (4)C13—H13A0.9800
C7—C81.372 (4)C13—H13B0.9800
C8—C91.419 (4)C13—H13C0.9800
C9—C101.416 (4)C15—H150.9500
C10—C111.365 (4)C17—H170.9500
C12—C131.540 (4)C18—H180.9500
C12—C141.532 (4)C19—H190.9500
C15—C161.469 (4)C20—H200.9500
C16—C211.391 (4)C21—H210.9500
C16—C171.405 (4)
C1—O1—C2117.7 (2)O1—C1—H1B109.00
N2—N1—C14119.9 (2)O1—C1—H1C110.00
N1—N2—C15114.7 (2)H1A—C1—H1B109.00
C14—N1—H1122 (2)H1A—C1—H1C109.00
N2—N1—H1118 (2)H1B—C1—H1C109.00
O1—C2—C11113.6 (3)C2—C3—H3120.00
O1—C2—C3125.8 (3)C4—C3—H3120.00
C3—C2—C11120.6 (3)C4—C5—H5120.00
C2—C3—C4120.0 (3)C6—C5—H5120.00
C5—C4—C9118.1 (3)C5—C6—H6119.00
C3—C4—C9119.7 (3)C7—C6—H6119.00
C3—C4—C5122.2 (3)C7—C8—H8119.00
C4—C5—C6120.8 (3)C9—C8—H8119.00
C5—C6—C7121.7 (3)C9—C10—H10119.00
C6—C7—C12118.6 (3)C11—C10—H10119.00
C6—C7—C8118.1 (3)C2—C11—H11120.00
C8—C7—C12123.2 (3)C10—C11—H11120.00
C7—C8—C9122.0 (3)C7—C12—H12108.00
C4—C9—C10118.1 (3)C13—C12—H12108.00
C4—C9—C8119.4 (3)C14—C12—H12108.00
C8—C9—C10122.5 (3)C12—C13—H13A109.00
C9—C10—C11121.5 (3)C12—C13—H13B109.00
C2—C11—C10120.0 (3)C12—C13—H13C109.00
C13—C12—C14107.5 (2)H13A—C13—H13B109.00
C7—C12—C14110.9 (2)H13A—C13—H13C110.00
C7—C12—C13114.7 (2)H13B—C13—H13C109.00
O2—C14—C12123.5 (2)N2—C15—H15120.00
O2—C14—N1123.4 (2)C16—C15—H15120.00
N1—C14—C12113.1 (2)C16—C17—H17120.00
N2—C15—C16120.6 (3)C18—C17—H17120.00
C15—C16—C17121.4 (3)C17—C18—H18120.00
C17—C16—C21118.6 (3)C19—C18—H18120.00
C15—C16—C21120.0 (3)C18—C19—H19120.00
C16—C17—C18120.1 (3)C20—C19—H19120.00
C17—C18—C19120.9 (3)C19—C20—H20120.00
C18—C19—C20119.4 (3)C21—C20—H20120.00
C19—C20—C21120.4 (3)C16—C21—H21120.00
C16—C21—C20120.7 (3)C20—C21—H21120.00
O1—C1—H1A110.00
C1—O1—C2—C3−0.5 (4)C6—C7—C12—C13−176.7 (3)
C1—O1—C2—C11178.8 (3)C6—C7—C12—C1461.4 (3)
C14—N1—N2—C15−176.1 (3)C8—C7—C12—C132.6 (4)
N2—N1—C14—O25.6 (4)C8—C7—C12—C14−119.4 (3)
N2—N1—C14—C12−171.5 (2)C7—C8—C9—C4−1.3 (4)
N1—N2—C15—C16−176.9 (2)C7—C8—C9—C10179.5 (3)
O1—C2—C3—C4179.6 (3)C4—C9—C10—C110.2 (4)
C11—C2—C3—C40.3 (4)C8—C9—C10—C11179.4 (3)
O1—C2—C11—C10−179.2 (3)C9—C10—C11—C2−0.4 (5)
C3—C2—C11—C100.1 (4)C7—C12—C14—O231.6 (4)
C2—C3—C4—C5178.9 (3)C7—C12—C14—N1−151.3 (3)
C2—C3—C4—C9−0.4 (4)C13—C12—C14—O2−94.4 (4)
C3—C4—C5—C6179.9 (3)C13—C12—C14—N182.6 (3)
C9—C4—C5—C6−0.8 (4)N2—C15—C16—C1720.1 (5)
C3—C4—C9—C8−179.0 (3)N2—C15—C16—C21−161.3 (3)
C3—C4—C9—C100.2 (4)C15—C16—C17—C18177.7 (3)
C5—C4—C9—C81.6 (4)C21—C16—C17—C18−0.9 (5)
C5—C4—C9—C10−179.2 (3)C15—C16—C21—C20−178.6 (3)
C4—C5—C6—C7−0.4 (4)C17—C16—C21—C200.0 (5)
C5—C6—C7—C80.7 (4)C16—C17—C18—C190.7 (5)
C5—C6—C7—C12180.0 (3)C17—C18—C19—C200.5 (5)
C6—C7—C8—C90.2 (4)C18—C19—C20—C21−1.5 (5)
C12—C7—C8—C9−179.1 (3)C19—C20—C21—C161.2 (5)
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.94 (3)1.98 (4)2.892 (3)163 (3)
C15—H15···O2i0.952.493.261 (3)138
C18—H18···O1ii0.952.593.209 (4)123
C1—H1C···Cg3iii0.982.913.696 (3)138
C12—H12···Cg2i1.002.783.661 (3)147
Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C4–C9 benzene and C16–C21 phenyl rings, respectively.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N1—H1⋯O2i 0.94 (3)1.98 (4)2.892 (3)163 (3)
C15—H15⋯O2i 0.952.493.261 (3)138
C18—H18⋯O1ii 0.952.593.209 (4)123
C1—H1C⋯Cg3iii 0.982.913.696 (3)138
C12—H12⋯Cg2i 1.002.783.661 (3)147

Symmetry codes: (i) ; (ii) ; (iii) .

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