(E)-1-(4-Meth-oxy-benzyl-idene)-2-phenyl-hydrazine.

In the title compound, C(14)H(14)N(2)O, the dihedral angle between the aromatic rings is 9.30 (6)°. In the crystal, mol-ecules are linked by C-H⋯π and N-H⋯π inter-actions.

Related literature

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

Experimental

Crystal data

C14H14N2O

M = 226.27

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.124

S = 1.01

3004 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.16 e Å−3

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002533X/hb5529Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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	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

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

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) ; (ii) .