N′-[(E)-2-Chloro­benzyl­idene]-2-(6-meth­oxy­naphthalen-2-yl)propano­hydrazide

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; Potgieter, H.; Albayati, M.R.

doi:10.1107/S1600536814008629

organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Pages o631-o632

doi:10.1107/S1600536814008629

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N′-[(E)-2-Chlorobenzylidene]-2-(6-methoxynaphthalen-2-yl)propanohydrazide

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Herman Potgieter ^e and Mustafa R. Albayati ^f ^*

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eAnalytical Development Division, Manchester Metropolitan University, Manchester M1 5GD, England, and ^fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

(Received 10 April 2014; accepted 16 April 2014; online 3 May 2014)

In the title compound, C₂₁H₁₉ClN₂O₂, the benzene ring and the naphthalene ring system are oriented at a dihedral angle of 65.24 (10)°. In the crystal, N—H⋯O, C—H⋯N and C—H⋯O hydrogen bonds link the molecules, forming chains along the b-axis direction. Further C—H⋯O hydrogen bonds link the chains, forming corrugated sheets lying parallel to (10-1).

CCDC reference: 997601

Related literature

For the use of Naproxen [systematic name: (+)-(S)-2-(6-methoxynaphthalen-2-yl)propanoic acid] and hydrazide-hydrazones in the treatment of disease and inflammation, see: Merlet et al. (2013 ); Almasirad et al. (2005 , 2006 ). For the harmful side-effects of non-steroidal anti-inflammatory drugs (NSAIDs), see: Uzgören-Baran et al. (2012 ); Tozkoparan et al. (2012 ). For the synthesis of NSAIDS with safer pro-drug profiles and enhanced chromphore efficacy, see: Koopaei et al. (2013 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₁H₁₉ClN₂O₂
M_r = 366.83
Monoclinic, P 2₁
a = 6.5703 (2) Å
b = 8.6166 (2) Å
c = 16.3411 (4) Å
β = 98.6850 (9)°
V = 914.52 (4) Å³
Z = 2
Cu Kα radiation
μ = 1.99 mm⁻¹
T = 100 K
0.23 × 0.09 × 0.02 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ) T_min = 0.87, T_max = 0.96
13492 measured reflections
3243 independent reflections
3122 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.064
S = 1.05
3243 reflections
237 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.12 e Å⁻³
Absolute structure: Flack parameter determined using 1358 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter: 0.056 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.91	1.93	2.829 (2)	169
C12—H12⋯N2ⁱ	1.00	2.48	3.444 (3)	163
C15—H15⋯O2ⁱ	0.95	2.48	3.259 (3)	139
C19—H19⋯O1ⁱⁱ	0.95	2.57	3.486 (3)	163
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (ii) x+1, y, z+1.

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

CCDC reference: 997601

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814008629/sj5398sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814008629/sj5398Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814008629/sj5398Isup3.cml

checkCIF report

Comment top

Naproxen ((+)-(S)-2-(6-methoxynaphthalen-2-yl)propanoic acid), among many non-steroidal anti-inflammatory drugs (NSAIDs), is used mainly in the treatment of pain, rehumatiod and inflammatory diseases (Merlet et al., 2013). It was reported that the presence of a carboxylic acid group in the parent drug leads to many undesirable side-effects such as gastrointestinal toxicity and ulceration (Uzgören-Baran et al., 2012; Tozkoparan et al., 2012). Recently, it was found that masking the carboxylic acid residue in the parent drug of NSAIDs led to safer pro-drug profiles and enhanced the chromophore efficacy (Koopaei et al., 2013). On the other hand, hydrazide-hydrazone scaffold compounds have been found to possess significant anti-inflammatory effects (Almasirad et al., 2005; Almasirad et al., 2006). Based on these findings the title compound was designed to be a hydrazone profile incorporating the Naproxen core structure without a carboxylic acid substituent.

The naphthalene ring system of the title compound (I, Fig.-1) is essentialy planar [maximum deviation = 0.025 (2) Å for C7 and -0.022 (2) Å for C9]. The dihedral angle between the mean planes of the naphthalene and phenyl groups is 65.24 (10)°. The C1–O1–C2–C11, C6–C7–C12–C13, C7–C12–C14–O2, C7–C12–C14–N1, C12–C14–N1–N2, O2–C14–N1–N2 and C14–N1–N2–C15 torsion angles are -3.6 (3), 28.5 (3), 82.8 (2), -95.9 (2), 177.67 (18), -3.6 (3) and 177.4 (2) °, respectively. In (I), the bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal structure, the N—H···O and C—H···N hydrogen bonds link the molecules, forming chains along the b-axis (Table 1 and Fig. 2). However, sensible C—H···O contacts are also present that link molecules into chains along c and extend the packing along the c axis.

Related literature top

For the use of Naproxen [systematic name: (+)-(S)-2-(6-methoxynaphthalen-2-yl)propanoic acid] and hydrazide-hydrazones in the treatment of disease and inflammation, see: Merlet et al. (2013); Almasirad et al. (2005, 2006). For the harmful side-effects of non-steroidal anti-inflammatory drugs (NSAIDs), see: Uzgören-Baran et al. (2012); Tozkoparan et al. (2012). For the synthesis of NSAIDS with safer pro-drug profiles and enhanced chromphore efficacy, see: Koopaei et al. (2013). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of 1 mmol (244 mg) Naproxen acid hydrazide [2-(6-methoxy-2-naphthyl)propanehydrazide] and 1 mmol (141 mg) 2-chlorobenzaldehyde was refluxed in 30 ml ethanol for 5hr in the presence of a few catalytic drops of glacial acetic acid. The mixture was cooled and separated, the solid filtered off, dried under vacuum and recrytallized from ethanol to furnish white crystals in a good quality suitable for X-ray diffraction. Mp 488–451 K.

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A perspective view of the title molecule with 50% probability ellipsoids.
	Fig. 2. Crystal packing viewed down the a axis showing hydrogen bonds as dotted lines (N—H···O: purple, C—H···O: black, C—H···N: green).

N'-[(E)-2-Chlorobenzylidene]-2-(6-methoxynaphthalen-2-yl)propanohydrazide top

Crystal data top

C₂₁H₁₉ClN₂O₂	F(000) = 384
M_r = 366.83	D_x = 1.332 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2yb	Cell parameters from 9961 reflections
a = 6.5703 (2) Å	θ = 2.7–68.2°
b = 8.6166 (2) Å	µ = 1.99 mm⁻¹
c = 16.3411 (4) Å	T = 100 K
β = 98.6850 (9)°	Plate, colourless
V = 914.52 (4) Å³	0.23 × 0.09 × 0.02 mm
Z = 2

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3243 independent reflections
Radiation source: INCOATEC IµS micro–focus source	3122 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.030
Detector resolution: 10.4167 pixels mm^-1	θ_max = 68.2°, θ_min = 2.7°
ω and ϕ scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −9→10
T_min = 0.87, T_max = 0.96	l = −19→19
13492 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.064	w = 1/[σ²(F_o²) + (0.0303P)² + 0.1372P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3243 reflections	Δρ_max = 0.20 e Å⁻³
237 parameters	Δρ_min = −0.12 e Å⁻³
1 restraint	Absolute structure: Flack parameter determined using 1358 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.056 (5)

Crystal data top

C₂₁H₁₉ClN₂O₂	V = 914.52 (4) Å³
M_r = 366.83	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 6.5703 (2) Å	µ = 1.99 mm⁻¹
b = 8.6166 (2) Å	T = 100 K
c = 16.3411 (4) Å	0.23 × 0.09 × 0.02 mm
β = 98.6850 (9)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3243 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	3122 reflections with I > 2σ(I)
T_min = 0.87, T_max = 0.96	R_int = 0.030
13492 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.064	Δρ_max = 0.20 e Å⁻³
S = 1.05	Δρ_min = −0.12 e Å⁻³
3243 reflections	Absolute structure: Flack parameter determined using 1358 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
237 parameters	Absolute structure parameter: 0.056 (5)
1 restraint

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	1.26515 (8)	0.49714 (7)	0.64924 (3)	0.0316 (2)
O1	0.4688 (2)	1.0112 (2)	−0.00565 (9)	0.0298 (5)
O2	0.3102 (2)	0.82203 (18)	0.49852 (9)	0.0270 (5)
N1	0.5530 (3)	0.6307 (2)	0.51581 (11)	0.0228 (6)
N2	0.6679 (3)	0.7022 (2)	0.58251 (11)	0.0244 (6)
C1	0.6649 (4)	0.9724 (4)	−0.02662 (17)	0.0422 (9)
C2	0.4163 (3)	0.9427 (3)	0.06423 (14)	0.0246 (7)
C3	0.2255 (3)	0.9925 (3)	0.08485 (12)	0.0251 (6)
C4	0.1563 (3)	0.9358 (3)	0.15342 (14)	0.0255 (7)
C5	0.2726 (3)	0.8254 (3)	0.20542 (13)	0.0217 (6)
C6	0.2070 (3)	0.7663 (3)	0.27802 (14)	0.0227 (7)
C7	0.3221 (3)	0.6596 (2)	0.32769 (14)	0.0220 (6)
C8	0.5082 (3)	0.6063 (3)	0.30327 (14)	0.0245 (7)
C9	0.5762 (3)	0.6609 (3)	0.23431 (14)	0.0246 (7)
C10	0.4627 (3)	0.7741 (2)	0.18331 (14)	0.0227 (6)
C11	0.5318 (3)	0.8356 (3)	0.11192 (14)	0.0235 (6)
C12	0.2624 (3)	0.5983 (3)	0.40812 (13)	0.0231 (7)
C13	0.0309 (3)	0.5967 (3)	0.41077 (14)	0.0272 (7)
C14	0.3743 (3)	0.6955 (2)	0.47855 (14)	0.0226 (7)
C15	0.8290 (3)	0.6268 (3)	0.61428 (14)	0.0236 (7)
C16	0.9609 (3)	0.6871 (3)	0.68768 (14)	0.0243 (7)
C17	0.8874 (4)	0.7958 (3)	0.73949 (14)	0.0294 (8)
C18	1.0113 (4)	0.8504 (3)	0.80960 (15)	0.0353 (8)
C19	1.2109 (4)	0.7965 (3)	0.82972 (16)	0.0387 (9)
C20	1.2888 (4)	0.6892 (3)	0.77994 (16)	0.0330 (8)
C21	1.1634 (4)	0.6351 (3)	0.70945 (15)	0.0276 (7)
H1	0.58750	0.53150	0.50470	0.0270*
H1A	0.77230	0.99770	0.01990	0.0630*
H1B	0.68830	1.03170	−0.07550	0.0630*
H1C	0.66940	0.86110	−0.03860	0.0630*
H3	0.14500	1.06600	0.05070	0.0300*
H4	0.02800	0.97060	0.16660	0.0310*
H6	0.08020	0.80120	0.29270	0.0270*
H8	0.58740	0.53030	0.33610	0.0290*
H9	0.70180	0.62280	0.22000	0.0300*
H11	0.65930	0.80210	0.09730	0.0280*
H12	0.31390	0.48930	0.41570	0.0280*
H13A	0.00370	0.53980	0.45990	0.0410*
H13B	−0.04030	0.54570	0.36090	0.0410*
H13C	−0.01910	0.70350	0.41320	0.0410*
H15	0.86290	0.53170	0.59020	0.0280*
H17	0.75010	0.83280	0.72640	0.0350*
H18	0.95920	0.92500	0.84390	0.0420*
H19	1.29500	0.83360	0.87820	0.0460*
H20	1.42620	0.65270	0.79360	0.0400*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0219 (3)	0.0340 (3)	0.0383 (3)	0.0029 (2)	0.0027 (2)	0.0080 (3)
O1	0.0250 (8)	0.0373 (9)	0.0268 (8)	0.0025 (8)	0.0030 (6)	0.0061 (8)
O2	0.0245 (8)	0.0235 (8)	0.0314 (9)	0.0027 (7)	−0.0005 (6)	0.0002 (7)
N1	0.0203 (10)	0.0203 (9)	0.0262 (10)	0.0012 (7)	−0.0014 (7)	−0.0004 (7)
N2	0.0211 (9)	0.0251 (10)	0.0256 (10)	−0.0019 (7)	−0.0007 (8)	0.0014 (8)
C1	0.0297 (13)	0.0577 (19)	0.0408 (14)	0.0070 (12)	0.0104 (11)	0.0197 (13)
C2	0.0245 (12)	0.0266 (12)	0.0214 (11)	−0.0034 (8)	−0.0003 (9)	−0.0032 (8)
C3	0.0248 (11)	0.0244 (10)	0.0242 (10)	0.0035 (10)	−0.0023 (8)	0.0000 (10)
C4	0.0208 (11)	0.0283 (11)	0.0260 (12)	0.0053 (9)	−0.0012 (9)	−0.0028 (9)
C5	0.0204 (11)	0.0210 (11)	0.0224 (11)	0.0010 (9)	−0.0011 (8)	−0.0044 (9)
C6	0.0168 (11)	0.0247 (11)	0.0258 (12)	0.0018 (8)	0.0009 (9)	−0.0050 (9)
C7	0.0193 (11)	0.0215 (11)	0.0242 (11)	−0.0021 (8)	−0.0003 (9)	−0.0037 (8)
C8	0.0199 (11)	0.0211 (11)	0.0310 (12)	0.0018 (8)	−0.0005 (9)	0.0013 (9)
C9	0.0168 (11)	0.0235 (11)	0.0331 (13)	0.0031 (8)	0.0028 (9)	−0.0031 (9)
C10	0.0198 (11)	0.0213 (11)	0.0258 (11)	−0.0007 (8)	−0.0005 (9)	−0.0065 (8)
C11	0.0195 (11)	0.0240 (11)	0.0267 (11)	0.0008 (9)	0.0023 (9)	−0.0038 (9)
C12	0.0190 (11)	0.0212 (11)	0.0279 (12)	0.0016 (8)	−0.0001 (9)	0.0021 (9)
C13	0.0211 (12)	0.0328 (13)	0.0272 (12)	−0.0011 (9)	0.0016 (10)	0.0029 (10)
C14	0.0194 (11)	0.0225 (11)	0.0261 (12)	0.0002 (8)	0.0039 (9)	0.0026 (9)
C15	0.0215 (11)	0.0234 (11)	0.0258 (12)	−0.0004 (9)	0.0033 (9)	0.0032 (9)
C16	0.0252 (12)	0.0234 (12)	0.0237 (11)	−0.0035 (8)	0.0016 (9)	0.0054 (8)
C17	0.0321 (13)	0.0267 (13)	0.0285 (13)	−0.0022 (9)	0.0019 (10)	0.0045 (9)
C18	0.0487 (16)	0.0289 (14)	0.0279 (13)	−0.0086 (11)	0.0045 (11)	−0.0003 (10)
C19	0.0438 (16)	0.0399 (16)	0.0281 (13)	−0.0181 (12)	−0.0080 (11)	0.0046 (11)
C20	0.0269 (12)	0.0356 (14)	0.0328 (14)	−0.0107 (10)	−0.0071 (10)	0.0107 (10)
C21	0.0250 (12)	0.0283 (13)	0.0285 (12)	−0.0051 (9)	0.0006 (10)	0.0092 (9)

Geometric parameters (Å, º) top

Cl1—C21	1.740 (3)	C16—C17	1.397 (3)
O1—C1	1.422 (3)	C17—C18	1.384 (3)
O1—C2	1.375 (3)	C18—C19	1.383 (4)
O2—C14	1.231 (2)	C19—C20	1.380 (4)
N1—N2	1.374 (3)	C20—C21	1.392 (4)
N1—C14	1.358 (3)	C1—H1A	0.9800
N2—C15	1.283 (3)	C1—H1B	0.9800
N1—H1	0.9100	C1—H1C	0.9800
C2—C11	1.362 (3)	C3—H3	0.9500
C2—C3	1.413 (3)	C4—H4	0.9500
C3—C4	1.362 (3)	C6—H6	0.9500
C4—C5	1.419 (3)	C8—H8	0.9500
C5—C6	1.417 (3)	C9—H9	0.9500
C5—C10	1.422 (3)	C11—H11	0.9500
C6—C7	1.375 (3)	C12—H12	1.0000
C7—C12	1.522 (3)	C13—H13A	0.9800
C7—C8	1.419 (3)	C13—H13B	0.9800
C8—C9	1.358 (3)	C13—H13C	0.9800
C9—C10	1.419 (3)	C15—H15	0.9500
C10—C11	1.417 (3)	C17—H17	0.9500
C12—C13	1.528 (3)	C18—H18	0.9500
C12—C14	1.520 (3)	C19—H19	0.9500
C15—C16	1.465 (3)	C20—H20	0.9500
C16—C21	1.398 (3)

C1—O1—C2	116.70 (19)	Cl1—C21—C20	117.8 (2)
N2—N1—C14	120.35 (17)	O1—C1—H1A	109.00
N1—N2—C15	114.50 (18)	O1—C1—H1B	109.00
N2—N1—H1	117.00	O1—C1—H1C	110.00
C14—N1—H1	121.00	H1A—C1—H1B	109.00
O1—C2—C3	114.2 (2)	H1A—C1—H1C	109.00
O1—C2—C11	125.31 (19)	H1B—C1—H1C	110.00
C3—C2—C11	120.5 (2)	C2—C3—H3	120.00
C2—C3—C4	120.4 (2)	C4—C3—H3	120.00
C3—C4—C5	121.10 (19)	C3—C4—H4	119.00
C6—C5—C10	119.4 (2)	C5—C4—H4	119.00
C4—C5—C6	122.54 (19)	C5—C6—H6	119.00
C4—C5—C10	118.05 (19)	C7—C6—H6	119.00
C5—C6—C7	121.66 (19)	C7—C8—H8	119.00
C6—C7—C8	118.1 (2)	C9—C8—H8	119.00
C6—C7—C12	123.46 (18)	C8—C9—H9	119.00
C8—C7—C12	118.43 (18)	C10—C9—H9	119.00
C7—C8—C9	121.8 (2)	C2—C11—H11	120.00
C8—C9—C10	121.1 (2)	C10—C11—H11	120.00
C5—C10—C11	119.72 (19)	C7—C12—H12	108.00
C9—C10—C11	122.36 (19)	C13—C12—H12	108.00
C5—C10—C9	117.92 (19)	C14—C12—H12	108.00
C2—C11—C10	120.28 (19)	C12—C13—H13A	109.00
C7—C12—C14	107.72 (18)	C12—C13—H13B	109.00
C7—C12—C13	114.52 (18)	C12—C13—H13C	110.00
C13—C12—C14	110.68 (18)	H13A—C13—H13B	109.00
N1—C14—C12	113.54 (17)	H13A—C13—H13C	109.00
O2—C14—C12	122.90 (19)	H13B—C13—H13C	110.00
O2—C14—N1	123.55 (19)	N2—C15—H15	120.00
N2—C15—C16	120.1 (2)	C16—C15—H15	120.00
C17—C16—C21	117.6 (2)	C16—C17—H17	119.00
C15—C16—C17	121.2 (2)	C18—C17—H17	119.00
C15—C16—C21	121.2 (2)	C17—C18—H18	120.00
C16—C17—C18	121.1 (2)	C19—C18—H18	120.00
C17—C18—C19	120.1 (2)	C18—C19—H19	120.00
C18—C19—C20	120.5 (2)	C20—C19—H19	120.00
C19—C20—C21	119.1 (2)	C19—C20—H20	120.00
C16—C21—C20	121.7 (2)	C21—C20—H20	120.00
Cl1—C21—C16	120.48 (19)

C1—O1—C2—C3	176.4 (2)	C8—C7—C12—C13	−152.7 (2)
C1—O1—C2—C11	−3.6 (3)	C8—C7—C12—C14	83.7 (2)
C14—N1—N2—C15	177.4 (2)	C7—C8—C9—C10	−0.2 (4)
N2—N1—C14—O2	3.6 (3)	C8—C9—C10—C5	−1.7 (3)
N2—N1—C14—C12	−177.67 (18)	C8—C9—C10—C11	178.7 (2)
N1—N2—C15—C16	−177.67 (19)	C5—C10—C11—C2	−0.4 (3)
O1—C2—C3—C4	−178.9 (2)	C9—C10—C11—C2	179.2 (2)
C11—C2—C3—C4	1.0 (4)	C7—C12—C14—O2	82.8 (2)
O1—C2—C11—C10	179.3 (2)	C7—C12—C14—N1	−95.9 (2)
C3—C2—C11—C10	−0.7 (4)	C13—C12—C14—O2	−43.1 (3)
C2—C3—C4—C5	−0.3 (4)	C13—C12—C14—N1	138.2 (2)
C3—C4—C5—C6	178.8 (2)	N2—C15—C16—C17	20.3 (3)
C3—C4—C5—C10	−0.8 (3)	N2—C15—C16—C21	−161.3 (2)
C4—C5—C6—C7	−179.9 (2)	C15—C16—C17—C18	178.8 (2)
C10—C5—C6—C7	−0.4 (3)	C21—C16—C17—C18	0.3 (4)
C4—C5—C10—C9	−178.5 (2)	C15—C16—C21—Cl1	0.3 (3)
C4—C5—C10—C11	1.1 (3)	C15—C16—C21—C20	−178.7 (2)
C6—C5—C10—C9	2.0 (3)	C17—C16—C21—Cl1	178.83 (19)
C6—C5—C10—C11	−178.4 (2)	C17—C16—C21—C20	−0.2 (4)
C5—C6—C7—C8	−1.5 (3)	C16—C17—C18—C19	−0.5 (4)
C5—C6—C7—C12	177.2 (2)	C17—C18—C19—C20	0.6 (4)
C6—C7—C8—C9	1.8 (3)	C18—C19—C20—C21	−0.4 (4)
C12—C7—C8—C9	−177.0 (2)	C19—C20—C21—Cl1	−178.8 (2)
C6—C7—C12—C13	28.5 (3)	C19—C20—C21—C16	0.2 (4)
C6—C7—C12—C14	−95.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.91	1.93	2.829 (2)	169
C12—H12···N2ⁱ	1.00	2.48	3.444 (3)	163
C15—H15···O2ⁱ	0.95	2.48	3.259 (3)	139
C19—H19···O1ⁱⁱ	0.95	2.57	3.486 (3)	163

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) x+1, y, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.91	1.93	2.829 (2)	169
C12—H12···N2ⁱ	1.00	2.48	3.444 (3)	163
C15—H15···O2ⁱ	0.95	2.48	3.259 (3)	139
C19—H19···O1ⁱⁱ	0.95	2.57	3.486 (3)	163

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) x+1, y, z+1.

Acknowledgements

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer is gratefully acknowledged.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Almasirad, A., Hosseini, R., Jalalizadeh, H., Rahimi-Moghaddam, Z., Abaeian, N., Janafrooz, M., Abbaspour, M., Ziaee, V., Dalvandi, A. & Shafiee, A. (2006). Biol. Pharm. Bull. 29, 1180–1185. Web of Science CrossRef PubMed CAS Google Scholar
Almasirad, A., Tajik, M., Bakhtiari, D., Shafiee, A., Abdollahi, M., Zamani, M. J. & Esmaily, H. (2005). J. Pharm. Pharm. Sci. 8, 419–425. Web of Science PubMed CAS Google Scholar
Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Koopaei, M. N., Assarzadeh, M. J., Almasirad, A., Ghasemi-Niri, S. F., Amini, M., Kebriaeezadeh, A., Koopaei, N. N., Ghadimi, M. & Tabei, A. (2013). Iran. J. Pharm. Res. 12, 721–727. CAS PubMed Google Scholar
Merlet, N., Busseuil, D., Rhéaume, E. & Tardif, J.-C. (2013). Anti-Inflamm. Anti-Allergy Agents Med. Chem. 12, 24–35. CrossRef CAS PubMed Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tozkoparan, B., Aytaç, S. P., Gürsoy, S. & Aktay, G. (2012). Med. Chem. Res. 21, 192–201. Web of Science CrossRef CAS Google Scholar
Uzgören-Baran, A., Tel, B. C., Deniz Sarıgöl, D., Öztürk, E. I., Kazkayası, I., Okay, G., Ertand, M. & Tozkoparan, B. (2012). Eur. J. Med. Chem. 57, 398–406. Web of Science PubMed Google Scholar

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Volume 70| Part 6| June 2014| Pages o631-o632

doi:10.1107/S1600536814008629

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N′-[(E)-2-Chloro­benzyl­­idene]-2-(6-meth­­oxy­naphthalen-2-yl)propano­hydrazide

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Experimental

Crystal data

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Refinement

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organic compounds

N′-[(E)-2-Chlorobenzylidene]-2-(6-methoxynaphthalen-2-yl)propanohydrazide