2-Methyl-benzaldehyde 2-methyl-benzyl-idenehydrazone.

The mol-ecule of the title compound, C(16)H(16)N(2), is centrosymmetric and the dihedral angle between the benzene ring and the dimethyl-hydrazine mean plane is 16.11 (15)°.

Related literature

For background, see: Shan et al. (2003 ▶). For related structures, see: Fan et al. (2008 ▶); Shan et al. (2004 ▶, 2008 ▶).

Experimental

Crystal data

C16H16N2

M = 236.31

Monoclinic,

a = 6.1578 (11) Å

b = 13.248 (2) Å

c = 8.8161 (16) Å

β = 105.398 (12)°

V = 693.4 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 295 (2) K

0.32 × 0.28 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: none

5451 measured reflections

1503 independent reflections

1168 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.115

S = 1.10

1503 reflections

84 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.10 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680801934X/hb2750sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801934X/hb2750Isup2.hkl

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

C16H16N2	F000 = 252
Mr = 236.31	Dx = 1.132 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2246 reflections
a = 6.1578 (11) Å	θ = 3.0–25.5º
b = 13.248 (2) Å	µ = 0.07 mm−1
c = 8.8161 (16) Å	T = 295 (2) K
β = 105.398 (12)º	Plate, yellow
V = 693.4 (2) Å3	0.32 × 0.28 × 0.12 mm
Z = 2

Rigaku R-AXIS RAPID IP diffractometer	1503 independent reflections
Radiation source: fine-focus sealed tube	1168 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
Detector resolution: 10.00 pixels mm-1	θmax = 27.0º
T = 295(2) K	θmin = 2.9º
ω scans	h = −7→7
Absorption correction: none	k = −15→16
5451 measured reflections	l = −11→11

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039	w = 1/[σ2(Fo2) + (0.0537P)2 + 0.0481P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.115	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.12 e Å−3
1503 reflections	Δρmin = −0.10 e Å−3
84 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.099 (12)
Secondary atom site location: difference Fourier map

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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
N	0.03959 (16)	0.45944 (7)	0.05193 (11)	0.0545 (3)
C1	0.33920 (18)	0.40583 (8)	0.26999 (12)	0.0495 (3)
C2	0.56653 (19)	0.41758 (9)	0.35123 (13)	0.0553 (3)
C3	0.6648 (2)	0.34407 (11)	0.46155 (15)	0.0731 (4)
H3	0.8162	0.3499	0.5151	0.088*
C4	0.5435 (3)	0.26319 (11)	0.49318 (18)	0.0813 (5)
H4	0.6129	0.2158	0.5682	0.098*
C5	0.3198 (3)	0.25229 (10)	0.41412 (16)	0.0754 (4)
H5	0.2377	0.1977	0.4356	0.090*
C6	0.2186 (2)	0.32277 (9)	0.30309 (14)	0.0617 (4)
H6	0.0678	0.3151	0.2492	0.074*
C7	0.22666 (19)	0.47938 (8)	0.15044 (13)	0.0514 (3)
H7	0.2935	0.5419	0.1466	0.062*
C8	0.7057 (2)	0.50502 (11)	0.32086 (16)	0.0720 (4)
H8A	0.6477	0.5668	0.3517	0.108*
H8B	0.6986	0.5078	0.2108	0.108*
H8C	0.8593	0.4963	0.3807	0.108*

	U11	U22	U33	U12	U13	U23
N	0.0577 (6)	0.0502 (6)	0.0522 (6)	0.0060 (4)	0.0086 (4)	0.0054 (4)
C1	0.0564 (6)	0.0494 (6)	0.0427 (6)	0.0049 (5)	0.0129 (5)	−0.0008 (5)
C2	0.0563 (7)	0.0624 (7)	0.0471 (6)	0.0058 (5)	0.0137 (5)	−0.0003 (5)
C3	0.0655 (8)	0.0849 (10)	0.0623 (8)	0.0139 (7)	0.0055 (6)	0.0119 (7)
C4	0.0945 (11)	0.0741 (9)	0.0686 (9)	0.0164 (8)	0.0097 (8)	0.0235 (7)
C5	0.0976 (11)	0.0571 (8)	0.0700 (9)	−0.0035 (7)	0.0198 (8)	0.0121 (6)
C6	0.0682 (8)	0.0567 (7)	0.0570 (7)	−0.0038 (6)	0.0112 (6)	0.0030 (5)
C7	0.0549 (6)	0.0492 (6)	0.0495 (6)	0.0012 (5)	0.0126 (5)	0.0009 (5)
C8	0.0568 (7)	0.0860 (10)	0.0711 (8)	−0.0059 (6)	0.0135 (6)	0.0053 (7)

N—C7	1.2727 (14)	C4—C5	1.376 (2)
N—Ni	1.4121 (17)	C4—H4	0.9300
C1—C6	1.4007 (16)	C5—C6	1.3764 (17)
C1—C2	1.4016 (16)	C5—H5	0.9300
C1—C7	1.4672 (15)	C6—H6	0.9300
C2—C3	1.3956 (17)	C7—H7	0.9300
C2—C8	1.5065 (17)	C8—H8A	0.9600
C3—C4	1.3761 (19)	C8—H8B	0.9600
C3—H3	0.9300	C8—H8C	0.9600
C7—N—Ni	112.25 (11)	C4—C5—H5	120.3
C6—C1—C2	119.57 (10)	C6—C5—H5	120.3
C6—C1—C7	119.74 (10)	C5—C6—C1	121.08 (12)
C2—C1—C7	120.70 (10)	C5—C6—H6	119.5
C3—C2—C1	117.90 (12)	C1—C6—H6	119.5
C3—C2—C8	119.92 (11)	N—C7—C1	121.44 (11)
C1—C2—C8	122.18 (10)	N—C7—H7	119.3
C4—C3—C2	121.77 (13)	C1—C7—H7	119.3
C4—C3—H3	119.1	C2—C8—H8A	109.5
C2—C3—H3	119.1	C2—C8—H8B	109.5
C5—C4—C3	120.20 (12)	H8A—C8—H8B	109.5
C5—C4—H4	119.9	C2—C8—H8C	109.5
C3—C4—H4	119.9	H8A—C8—H8C	109.5
C4—C5—C6	119.48 (13)	H8B—C8—H8C	109.5