(E)-1-(4-Meth­oxy­benzyl­idene)-2-phenyl­hydrazine

Mufakkar, M.; Tahir, M.N.; Tariq, M.I.; Ahmad, S.; Sarfraz, M.

doi:10.1107/S160053681002533X

organic compounds

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Volume 66| Part 8| August 2010| Page o1887

https://doi.org/10.1107/S160053681002533X

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(E)-1-(4-Methoxybenzylidene)-2-phenylhydrazine

Muhammad Mufakkar,^a M. Nawaz Tahir,^b ^* Muhammad Ilyas Tariq,^c Shahbaz Ahmad ^c and Muhammad Sarfraz ^c

^aDepartment of Chemistry, Government College University, Lahore, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^cDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 27 June 2010; accepted 28 June 2010; online 3 July 2010)

In the title compound, C₁₄H₁₄N₂O, the dihedral angle between the aromatic rings is 9.30 (6)°. In the crystal, molecules are linked by C—H⋯π and N—H⋯π interactions.

Related literature

For related structures, see: Tunç et al. (2003 ); Harada et al. (2004 ).

Experimental

Crystal data

C₁₄H₁₄N₂O
M_r = 226.27
Monoclinic, P 2₁ /n
a = 5.8021 (2) Å
b = 7.5819 (2) Å
c = 27.7907 (9) Å
β = 95.808 (1)°
V = 1216.26 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.30 × 0.16 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.942, T_max = 0.959
18675 measured reflections
3004 independent reflections
2257 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.124
S = 1.01
3004 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cg1ⁱ	0.86	2.69	3.3484 (13)	146
C3—H3⋯Cg1ⁱⁱ	0.93	2.63	3.3796 (14)	138
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681002533X/hb5529sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681002533X/hb5529Isup2.hkl

checkCIF report

Comment top

The crystal structure of (II) i.e., N-(4-methoxybenzylidene)-N^'-(2-pyridyl)hydrazine (Tunç et al. 2003) and N-(4-methoxybenzylidene)aniline (Harada et al. 2004) have been published which are related to the title compound (I, Fig. 1).

In (I) the phenyl ring A (C1–C6) of phenylhydrazide and B (C8–C13) of 4-anisaldehyde are planar with r. m. s. deviation of 0.0015 and 0.0096 Å, respectively. The dihedral angle between A/B is 9.30 (6)°. The central group C (N1/N2/C7) is of course planar and the orientation of A/C and B/C is 11.59 (17) and 2.89 (18)°, respectively. The molecules are essentially monomer. Due to the packing and unavailabilty of strong acceptor atom, the H-atom of N—H is not directly involved in H-bonding. The molecules are stabilized through C—H···π and N—H···π interactions (Table 1).

Related literature top

For related structures, see: Tunç et al. (2003); Harada et al. (2004).

Experimental top

Equimolar quantities of phenylhydrazine and 4-methoxybenzaldehyde were refluxed in methanol for 45 min resulting in yellow solution. The solution was kept at room temperature which affoarded yellow needles of (I) after 72 h.

Structure description top

For related structures, see: Tunç et al. (2003); Harada et al. (2004).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. View of (I) with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown by circles of arbitrary radius.

(E)-1-(4-Methoxybenzylidene)-2-phenylhydrazine top

Crystal data top

C₁₄H₁₄N₂O	F(000) = 480
M_r = 226.27	D_x = 1.236 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2257 reflections
a = 5.8021 (2) Å	θ = 2.8–28.4°
b = 7.5819 (2) Å	µ = 0.08 mm⁻¹
c = 27.7907 (9) Å	T = 296 K
β = 95.808 (1)°	Cut needle, yellow
V = 1216.26 (7) Å³	0.30 × 0.16 × 0.14 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3004 independent reflections
Radiation source: fine-focus sealed tube	2257 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 8.20 pixels mm^-1	θ_max = 28.4°, θ_min = 2.8°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→10
T_min = 0.942, T_max = 0.959	l = −37→37
18675 measured 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0582P)² + 0.2017P] where P = (F_o² + 2F_c²)/3
3004 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₄H₁₄N₂O	V = 1216.26 (7) Å³
M_r = 226.27	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.8021 (2) Å	µ = 0.08 mm⁻¹
b = 7.5819 (2) Å	T = 296 K
c = 27.7907 (9) Å	0.30 × 0.16 × 0.14 mm
β = 95.808 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3004 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2257 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.959	R_int = 0.028
18675 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.01	Δρ_max = 0.17 e Å⁻³
3004 reflections	Δρ_min = −0.16 e Å⁻³
155 parameters

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 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	U_iso*/U_eq
O1	0.58571 (17)	0.12817 (13)	0.05523 (3)	0.0593 (3)
N1	1.0199 (2)	0.27807 (16)	0.32418 (4)	0.0576 (4)
N2	0.99619 (18)	0.22429 (14)	0.27710 (4)	0.0475 (3)
C1	1.1991 (2)	0.21880 (15)	0.35653 (4)	0.0431 (4)
C2	1.3896 (2)	0.13069 (16)	0.34188 (5)	0.0486 (4)
C3	1.5625 (2)	0.07433 (18)	0.37608 (6)	0.0594 (5)
C4	1.5495 (3)	0.1038 (2)	0.42465 (6)	0.0659 (5)
C5	1.3613 (3)	0.1917 (2)	0.43908 (5)	0.0616 (5)
C6	1.1872 (2)	0.24896 (17)	0.40553 (5)	0.0520 (4)
C7	0.8064 (2)	0.26802 (16)	0.25267 (4)	0.0458 (4)
C8	0.7500 (2)	0.22464 (14)	0.20197 (4)	0.0404 (3)
C9	0.9001 (2)	0.13387 (15)	0.17420 (4)	0.0436 (4)
C10	0.8384 (2)	0.10202 (16)	0.12601 (4)	0.0458 (4)
C11	0.6270 (2)	0.16101 (15)	0.10379 (4)	0.0438 (4)
C12	0.4738 (2)	0.24744 (16)	0.13072 (4)	0.0458 (4)
C13	0.5363 (2)	0.27705 (16)	0.17934 (4)	0.0449 (4)
C14	0.3755 (3)	0.1915 (3)	0.03100 (5)	0.0771 (6)
H1	0.92065	0.35071	0.33393	0.0691*
H2	1.40053	0.10982	0.30922	0.0583*
H3	1.69010	0.01538	0.36620	0.0713*
H4	1.66685	0.06457	0.44740	0.0791*
H5	1.35170	0.21259	0.47179	0.0739*
H6	1.06052	0.30834	0.41570	0.0624*
H7	0.69829	0.33119	0.26824	0.0550*
H9	1.04277	0.09490	0.18855	0.0523*
H10	0.93876	0.04044	0.10807	0.0550*
H12	0.33060	0.28509	0.11628	0.0550*
H13	0.43235	0.33379	0.19749	0.0539*
H14A	0.24713	0.13841	0.04481	0.1156*
H14B	0.36847	0.16173	−0.00269	0.1156*
H14C	0.36828	0.31731	0.03446	0.1156*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0679 (6)	0.0706 (6)	0.0389 (5)	0.0039 (5)	0.0023 (4)	−0.0054 (4)
N1	0.0616 (7)	0.0695 (7)	0.0400 (6)	0.0237 (6)	−0.0038 (5)	−0.0104 (5)
N2	0.0537 (6)	0.0484 (6)	0.0398 (6)	0.0048 (4)	0.0018 (5)	−0.0027 (4)
C1	0.0458 (6)	0.0395 (6)	0.0431 (7)	0.0005 (5)	0.0004 (5)	−0.0025 (5)
C2	0.0480 (7)	0.0464 (6)	0.0512 (7)	−0.0004 (5)	0.0045 (5)	−0.0080 (5)
C3	0.0476 (7)	0.0518 (7)	0.0771 (10)	0.0065 (6)	−0.0020 (7)	−0.0102 (7)
C4	0.0627 (9)	0.0603 (8)	0.0690 (10)	0.0073 (7)	−0.0207 (7)	−0.0022 (7)
C5	0.0714 (9)	0.0650 (9)	0.0458 (8)	0.0017 (7)	−0.0066 (7)	−0.0033 (6)
C6	0.0560 (7)	0.0546 (8)	0.0452 (7)	0.0065 (6)	0.0035 (6)	−0.0055 (5)
C7	0.0503 (7)	0.0449 (6)	0.0421 (7)	0.0051 (5)	0.0038 (5)	−0.0012 (5)
C8	0.0444 (6)	0.0370 (5)	0.0400 (6)	−0.0027 (4)	0.0048 (5)	0.0016 (4)
C9	0.0412 (6)	0.0434 (6)	0.0462 (7)	0.0004 (5)	0.0044 (5)	0.0036 (5)
C10	0.0465 (6)	0.0467 (6)	0.0458 (7)	0.0008 (5)	0.0125 (5)	−0.0029 (5)
C11	0.0509 (7)	0.0430 (6)	0.0376 (6)	−0.0061 (5)	0.0050 (5)	−0.0006 (5)
C12	0.0413 (6)	0.0495 (7)	0.0457 (7)	−0.0009 (5)	−0.0004 (5)	−0.0010 (5)
C13	0.0435 (6)	0.0460 (6)	0.0456 (7)	0.0027 (5)	0.0070 (5)	−0.0024 (5)
C14	0.0929 (12)	0.0906 (12)	0.0443 (8)	0.0169 (10)	−0.0095 (8)	−0.0024 (8)

Geometric parameters (Å, º) top

O1—C11	1.3694 (14)	C10—C11	1.3902 (16)
O1—C14	1.416 (2)	C11—C12	1.3836 (16)
N1—N2	1.3641 (16)	C12—C13	1.3815 (16)
N1—C1	1.3792 (16)	C2—H2	0.9300
N2—C7	1.2776 (16)	C3—H3	0.9300
N1—H1	0.8600	C4—H4	0.9300
C1—C6	1.3894 (18)	C5—H5	0.9300
C1—C2	1.3874 (17)	C6—H6	0.9300
C2—C3	1.3782 (19)	C7—H7	0.9300
C3—C4	1.378 (2)	C9—H9	0.9300
C4—C5	1.373 (2)	C10—H10	0.9300
C5—C6	1.374 (2)	C12—H12	0.9300
C7—C8	1.4516 (16)	C13—H13	0.9300
C8—C13	1.3903 (16)	C14—H14A	0.9600
C8—C9	1.4013 (16)	C14—H14B	0.9600
C9—C10	1.3722 (16)	C14—H14C	0.9600

C11—O1—C14	117.60 (10)	C3—C2—H2	120.00
N2—N1—C1	121.61 (11)	C2—C3—H3	119.00
N1—N2—C7	115.47 (11)	C4—C3—H3	119.00
N2—N1—H1	119.00	C3—C4—H4	120.00
C1—N1—H1	119.00	C5—C4—H4	120.00
N1—C1—C2	122.42 (11)	C4—C5—H5	120.00
N1—C1—C6	118.45 (11)	C6—C5—H5	120.00
C2—C1—C6	119.14 (11)	C1—C6—H6	120.00
C1—C2—C3	119.53 (12)	C5—C6—H6	120.00
C2—C3—C4	121.14 (13)	N2—C7—H7	118.00
C3—C4—C5	119.26 (14)	C8—C7—H7	118.00
C4—C5—C6	120.46 (13)	C8—C9—H9	120.00
C1—C6—C5	120.47 (12)	C10—C9—H9	120.00
N2—C7—C8	123.68 (11)	C9—C10—H10	120.00
C9—C8—C13	117.82 (10)	C11—C10—H10	120.00
C7—C8—C9	123.66 (10)	C11—C12—H12	120.00
C7—C8—C13	118.52 (10)	C13—C12—H12	120.00
C8—C9—C10	120.57 (11)	C8—C13—H13	119.00
C9—C10—C11	120.55 (11)	C12—C13—H13	119.00
O1—C11—C12	124.15 (11)	O1—C14—H14A	109.00
O1—C11—C10	115.96 (10)	O1—C14—H14B	109.00
C10—C11—C12	119.89 (10)	O1—C14—H14C	109.00
C11—C12—C13	119.12 (11)	H14A—C14—H14B	109.00
C8—C13—C12	121.99 (11)	H14A—C14—H14C	109.00
C1—C2—H2	120.00	H14B—C14—H14C	109.00

C14—O1—C11—C12	1.90 (19)	C4—C5—C6—C1	0.0 (2)
C14—O1—C11—C10	−177.93 (13)	N2—C7—C8—C13	179.04 (12)
N2—N1—C1—C2	13.07 (18)	N2—C7—C8—C9	−1.57 (19)
N2—N1—C1—C6	−166.94 (11)	C7—C8—C13—C12	177.18 (11)
C1—N1—N2—C7	170.35 (11)	C9—C8—C13—C12	−2.24 (17)
N1—N2—C7—C8	179.36 (11)	C7—C8—C9—C10	−177.96 (11)
N1—C1—C6—C5	179.76 (12)	C13—C8—C9—C10	1.44 (17)
N1—C1—C2—C3	−179.78 (12)	C8—C9—C10—C11	0.73 (18)
C6—C1—C2—C3	0.24 (18)	C9—C10—C11—C12	−2.17 (18)
C2—C1—C6—C5	−0.26 (19)	C9—C10—C11—O1	177.67 (11)
C1—C2—C3—C4	0.1 (2)	O1—C11—C12—C13	−178.45 (11)
C2—C3—C4—C5	−0.3 (2)	C10—C11—C12—C13	1.38 (18)
C3—C4—C5—C6	0.3 (2)	C11—C12—C13—C8	0.85 (18)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C8–C13 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cg1ⁱ	0.86	2.69	3.3484 (13)	146
C3—H3···Cg1ⁱⁱ	0.93	2.63	3.3796 (14)	138

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+5/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₂O
M_r	226.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	5.8021 (2), 7.5819 (2), 27.7907 (9)
β (°)	95.808 (1)
V (Å³)	1216.26 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.16 × 0.14

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.942, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	18675, 3004, 2257
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.124, 1.01
No. of reflections	3004
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.16

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SAINT, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C8–C13 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cg1ⁱ	0.86	2.69	3.3484 (13)	146
C3—H3···Cg1ⁱⁱ	0.93	2.63	3.3796 (14)	138

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+5/2, y−1/2, −z+1/2.

Acknowledgements

The authors acknowledge the provision of funds for the purchase of diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Harada, J., Harakawa, M. & Ogawa, K. (2004). Acta Cryst. B60, 578–588. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tunç, T., Sarı, M., Yagbasan, R., Tezcan, H. & Şahin, E. (2003). Acta Cryst. C59, o192–o193. Web of Science CSD CrossRef IUCr Journals Google Scholar

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