Literature DB >> 22719588

N'-(3-Hy-droxy-benzyl-idene)-4-methyl-benzohydrazide.

Abstract

The title compound, C(15)H(14)N(2)O(2), was obtained from the reaction of 3-hy-droxy-benzaldhyde and 4-methyl-benzo-hydrazide in methanol. In the mol-ecule, the benzene rings form a dihedral angle of 2.9 (3)°. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules into layers parallel to (101). The crystal packing also exhibits π-π inter-actions between the aromatic rings [centroid-centroid distance = 3.686 (4) Å].

Entities: Chemical Disease Species

Year: 2012 PMID： 22719588 PMCID： PMC3379390 DOI： 10.1107/S1600536812021897

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the biological activity of benzohydrazide compounds, see: El-Sayed et al. (2011 ▶); Horiuchi et al. (2009 ▶). For benzohydrazide coordination compounds, see: El-Dissouky et al. (2010 ▶); Zhang et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For the crystal structures of similar compounds, see: Suleiman Gwaram et al. (2010 ▶); Liu et al. (2011 ▶); Zhang et al. (2012 ▶).

Experimental

Crystal data

C15H14N2O2 M = 254.28 Monoclinic, a = 11.5203 (14) Å b = 8.7228 (12) Å c = 13.5793 (19) Å β = 106.889 (2)° V = 1305.7 (3) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 298 K 0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.985, T max = 0.987 5767 measured reflections 2193 independent reflections 1013 reflections with I > 2σ(I) R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.057 wR(F 2) = 0.160 S = 0.96 2193 reflections 176 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.19 e Å−3 Δρmin = −0.19 e Å−3 Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812021897/cv5303sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021897/cv5303Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812021897/cv5303Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₁₄N₂O₂	F(000) = 536
M_r = 254.28	D_x = 1.294 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.5203 (14) Å	Cell parameters from 1383 reflections
b = 8.7228 (12) Å	θ = 2.7–27.8°
c = 13.5793 (19) Å	µ = 0.09 mm⁻¹
β = 106.889 (2)°	T = 298 K
V = 1305.7 (3) Å³	Prism, colourless
Z = 4	0.17 × 0.15 × 0.15 mm

Bruker SMART 1K CCD area-detector diffractometer	2193 independent reflections
Radiation source: fine-focus sealed tube	1013 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
ω scan	θ_max = 25.1°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→13
T_min = 0.985, T_max = 0.987	k = −10→10
5767 measured reflections	l = −16→11

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ²(F_o²) + (0.0672P)²] where P = (F_o² + 2F_c²)/3
2193 reflections	(Δ/σ)_max < 0.001
176 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³

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	U_iso*/U_eq
N1	0.0696 (3)	0.2934 (3)	1.0157 (2)	0.0449 (8)
N2	0.0285 (3)	0.3619 (3)	0.9196 (2)	0.0443 (8)
O1	0.2096 (3)	0.4735 (3)	0.93581 (19)	0.0626 (8)
O2	0.2664 (2)	0.0955 (3)	1.37553 (19)	0.0625 (8)
H2B	0.2708	0.0441	1.4271	0.094*
C1	0.0236 (3)	0.1217 (4)	1.1365 (3)	0.0392 (9)
C2	0.1324 (3)	0.1476 (4)	1.2118 (3)	0.0434 (10)
H2A	0.1869	0.2198	1.2012	0.052*
C3	0.1591 (4)	0.0654 (4)	1.3023 (3)	0.0437 (10)
C4	0.0790 (4)	−0.0422 (4)	1.3187 (3)	0.0509 (10)
H4	0.0979	−0.0978	1.3797	0.061*
C5	−0.0290 (4)	−0.0666 (4)	1.2441 (3)	0.0565 (11)
H5	−0.0833	−0.1390	1.2548	0.068*
C6	−0.0575 (3)	0.0154 (4)	1.1533 (3)	0.0506 (10)
H6	−0.1312	−0.0009	1.1034	0.061*
C7	−0.0067 (3)	0.2051 (4)	1.0389 (3)	0.0451 (10)
H7	−0.0835	0.1934	0.9927	0.054*
C8	0.1044 (4)	0.4477 (4)	0.8839 (3)	0.0427 (10)
C9	0.0544 (4)	0.5105 (3)	0.7790 (3)	0.0410 (9)
C10	0.1221 (4)	0.6163 (4)	0.7431 (3)	0.0578 (11)
H10	0.1989	0.6433	0.7844	0.069*
C11	0.0779 (5)	0.6825 (4)	0.6472 (3)	0.0640 (12)
H11	0.1259	0.7524	0.6251	0.077*
C12	−0.0351 (4)	0.6480 (4)	0.5838 (3)	0.0557 (11)
C13	−0.1021 (4)	0.5414 (4)	0.6183 (3)	0.0566 (11)
H13	−0.1784	0.5141	0.5762	0.068*
C14	−0.0587 (4)	0.4735 (4)	0.7144 (3)	0.0520 (11)
H14	−0.1064	0.4021	0.7356	0.062*
C15	−0.0846 (4)	0.7240 (5)	0.4805 (3)	0.0806 (14)
H15A	−0.1681	0.7508	0.4704	0.121*
H15B	−0.0787	0.6547	0.4273	0.121*
H15C	−0.0387	0.8150	0.4780	0.121*
H2	−0.0506 (13)	0.367 (4)	0.884 (3)	0.080*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.052 (2)	0.0353 (16)	0.0438 (19)	0.0031 (16)	0.0086 (17)	0.0024 (14)
N2	0.050 (2)	0.0366 (16)	0.0432 (19)	0.0005 (17)	0.0079 (17)	0.0067 (15)
O1	0.059 (2)	0.0708 (19)	0.0540 (17)	−0.0164 (15)	0.0102 (16)	−0.0015 (14)
O2	0.057 (2)	0.0703 (19)	0.0532 (17)	−0.0046 (15)	0.0047 (16)	0.0127 (14)
C1	0.045 (3)	0.0292 (18)	0.042 (2)	0.0046 (17)	0.010 (2)	−0.0003 (17)
C2	0.051 (3)	0.0307 (19)	0.051 (2)	−0.0002 (17)	0.018 (2)	−0.0006 (18)
C3	0.048 (3)	0.038 (2)	0.044 (2)	0.0030 (19)	0.012 (2)	0.0028 (18)
C4	0.063 (3)	0.038 (2)	0.051 (2)	0.000 (2)	0.017 (2)	0.0076 (19)
C5	0.071 (3)	0.039 (2)	0.062 (3)	−0.015 (2)	0.023 (3)	0.002 (2)
C6	0.054 (3)	0.038 (2)	0.055 (3)	−0.0064 (19)	0.008 (2)	−0.0009 (19)
C7	0.051 (3)	0.0312 (19)	0.049 (2)	0.0020 (19)	0.007 (2)	−0.0005 (18)
C8	0.052 (3)	0.0309 (19)	0.046 (2)	−0.0014 (19)	0.015 (2)	−0.0078 (18)
C9	0.053 (3)	0.0257 (18)	0.046 (2)	−0.0005 (18)	0.018 (2)	−0.0020 (17)
C10	0.062 (3)	0.052 (2)	0.061 (3)	−0.011 (2)	0.021 (2)	−0.003 (2)
C11	0.091 (4)	0.046 (2)	0.068 (3)	−0.011 (2)	0.043 (3)	0.010 (2)
C12	0.076 (3)	0.038 (2)	0.061 (3)	0.018 (2)	0.033 (3)	0.005 (2)
C13	0.062 (3)	0.052 (2)	0.054 (3)	0.002 (2)	0.015 (2)	0.005 (2)
C14	0.063 (3)	0.040 (2)	0.054 (3)	−0.003 (2)	0.018 (2)	0.0041 (19)
C15	0.114 (4)	0.066 (3)	0.068 (3)	0.029 (3)	0.037 (3)	0.026 (2)

N1—C7	1.276 (4)	C6—H6	0.9300
N1—N2	1.388 (4)	C7—H7	0.9300
N2—C8	1.344 (4)	C8—C9	1.478 (5)
N2—H2	0.898 (10)	C9—C14	1.381 (4)
O1—C8	1.233 (4)	C9—C10	1.385 (5)
O2—C3	1.368 (4)	C10—C11	1.379 (5)
O2—H2B	0.8200	C10—H10	0.9300
C1—C6	1.380 (4)	C11—C12	1.369 (5)
C1—C2	1.386 (4)	C11—H11	0.9300
C1—C7	1.463 (4)	C12—C13	1.374 (5)
C2—C3	1.378 (4)	C12—C15	1.506 (5)
C2—H2A	0.9300	C13—C14	1.388 (4)
C3—C4	1.379 (4)	C13—H13	0.9300
C4—C5	1.374 (5)	C14—H14	0.9300
C4—H4	0.9300	C15—H15A	0.9600
C5—C6	1.381 (5)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600

C7—N1—N2	114.9 (3)	O1—C8—C9	121.8 (4)
C8—N2—N1	119.9 (3)	N2—C8—C9	116.2 (4)
C8—N2—H2	117 (3)	C14—C9—C10	117.1 (3)
N1—N2—H2	122 (3)	C14—C9—C8	123.8 (3)
C3—O2—H2B	109.5	C10—C9—C8	119.0 (4)
C6—C1—C2	119.9 (3)	C11—C10—C9	121.3 (4)
C6—C1—C7	119.2 (4)	C11—C10—H10	119.3
C2—C1—C7	120.9 (3)	C9—C10—H10	119.3
C3—C2—C1	119.5 (3)	C12—C11—C10	121.6 (4)
C3—C2—H2A	120.2	C12—C11—H11	119.2
C1—C2—H2A	120.2	C10—C11—H11	119.2
O2—C3—C2	118.0 (3)	C11—C12—C13	117.4 (4)
O2—C3—C4	121.3 (3)	C11—C12—C15	121.5 (4)
C2—C3—C4	120.7 (4)	C13—C12—C15	121.1 (4)
C5—C4—C3	119.5 (4)	C12—C13—C14	121.6 (4)
C5—C4—H4	120.3	C12—C13—H13	119.2
C3—C4—H4	120.3	C14—C13—H13	119.2
C4—C5—C6	120.5 (4)	C9—C14—C13	120.9 (4)
C4—C5—H5	119.7	C9—C14—H14	119.6
C6—C5—H5	119.7	C13—C14—H14	119.6
C1—C6—C5	119.9 (4)	C12—C15—H15A	109.5
C1—C6—H6	120.1	C12—C15—H15B	109.5
C5—C6—H6	120.1	H15A—C15—H15B	109.5
N1—C7—C1	121.6 (4)	C12—C15—H15C	109.5
N1—C7—H7	119.2	H15A—C15—H15C	109.5
C1—C7—H7	119.2	H15B—C15—H15C	109.5
O1—C8—N2	122.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.90 (1)	2.10 (2)	2.926 (4)	152 (3)
O2—H2B···O1ⁱⁱ	0.82	1.91	2.713 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.90 (1)	2.10 (2)	2.926 (4)	152 (3)
O2—H2B⋯O1ⁱⁱ	0.82	1.91	2.713 (3)	166

Symmetry codes: (i) ; (ii) .

6 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. N'-[1-(5-Bromo-2-hydroxy-phen-yl)ethyl-idene]-3,4,5-trihydroxy-benzohydrazide dimethyl sulfoxide solvate trihydrate.

Authors: Nura Suleiman Gwaram; Hamid Khaledi; Hapipah Mohd Ali; Ward T Robinson; Mahmood A Abdulla
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-02-27

3. Discovery of novel thieno[2,3-d]pyrimidin-4-yl hydrazone-based inhibitors of cyclin D1-CDK4: synthesis, biological evaluation and structure-activity relationships. Part 2.

Authors: Takao Horiuchi; Motoko Nagata; Mayumi Kitagawa; Kouichi Akahane; Kouichi Uoto
Journal: Bioorg Med Chem Date: 2009-10-24 Impact factor: 3.641