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

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 mol-ecules, forming chains along the b-axis direction. Further C-H⋯O hydrogen bonds link the chains, forming corrugated sheets lying parallel to (10-1).

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 = 366.83

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.064

S = 1.05

3243 reflections

237 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −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)

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814008629/sj5398sup1.cif

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

Click here for additional data file.

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

CCDC reference: 997601

Additional supporting information: crystallographic information; 3D view; checkCIF report

C21H19ClN2O2	F(000) = 384
Mr = 366.83	Dx = 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

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	Rint = 0.030
Detector resolution: 10.4167 pixels mm-1	θmax = 68.2°, θmin = 2.7°
ω and φ scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −9→10
Tmin = 0.87, Tmax = 0.96	l = −19→19
13492 measured reflections

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(Fo2) + (0.0303P)2 + 0.1372P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3243 reflections	Δρmax = 0.20 e Å−3
237 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .