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organic compounds
(E)-1-(4-Methoxybenzylidene)-2-phenylhydrazine
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
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.
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2009); cell 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
https://doi.org/10.1107/S160053681002533X/hb5529sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681002533X/hb5529Isup2.hkl
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.
Although all H-atoms appear in the difference Fourier map but were positioned geometrically (N–H = 0.86, C–H = 0.93–0.96 Å) and refined as riding with Uiso(H) = xUeq(C, N), where x = 1.5 for methyl and x = 1.2 for all other H-atoms.
The
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).
For related structures, see: Tunç et al. (2003); Harada et al. (2004).
Data collection: APEX2 (Bruker, 2009); cell
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). ![]() | Fig. 1. View of (I) with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown by circles of arbitrary radius. |
C14H14N2O | F(000) = 480 |
Mr = 226.27 | Dx = 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 |
Bruker Kappa APEXII CCD diffractometer | 3004 independent reflections |
Radiation source: fine-focus sealed tube | 2257 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 8.20 pixels mm-1 | θmax = 28.4°, θmin = 2.8° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −9→10 |
Tmin = 0.942, Tmax = 0.959 | l = −37→37 |
18675 measured reflections |
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(Fo2) + (0.0582P)2 + 0.2017P] where P = (Fo2 + 2Fc2)/3 |
3004 reflections | (Δ/σ)max < 0.001 |
155 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C14H14N2O | V = 1216.26 (7) Å3 |
Mr = 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)° |
Bruker Kappa APEXII CCD diffractometer | 3004 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 2257 reflections with I > 2σ(I) |
Tmin = 0.942, Tmax = 0.959 | Rint = 0.028 |
18675 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.17 e Å−3 |
3004 reflections | Δρmin = −0.16 e Å−3 |
155 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.942, 0.959 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18675, 3004, 2257 |
Rint | 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 |
Δρmax, Δρmin (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).
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
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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).