Literature DB >> 24826134

1,5-Bis(2-hy-droxy-3-meth-oxy-benzyl-idene)carbonohydrazide methanol 0.47-solvate.

Mouhamadou Moustapha Sow¹, Ousmane Diouf¹, Matar Seck², Aliou Hamady Barry³, Mohamed Gaye¹.

Abstract

In the title compound, C17H18N4O5·0.47CH3OH, the virtually planar (r.m.s. deviation = 0.128 Å) carbonohydrazide mol-ecule is located on a twofold axis and conformation of its C=N bonds is E. There are short intra-molecular O-H⋯N hydrogen bonds between the hy-droxy groups and hydrazide N atoms. In the crystal, bifurcated N-H⋯(O,O) hydrogen bonds assemble the carbonohydrazide mol-ecules into a three-dimensional network. There are C 2 symmetric voids in this network, 47% of which are occupied by disordered methanol mol-ecules.

Entities: Chemical Disease Gene

Year: 2014 PMID： 24826134 PMCID： PMC3998575 DOI： 10.1107/S1600536814004802

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

Related literature

For related structures, see: Du & Zhang (2010 ▶); He et al. (2010 ▶); Kong et al. (2010 ▶). For the biological activity of carbonohydrazides, see: Bacchi et al. (1999 ▶); El-Gammal et al. (2012 ▶).

Experimental

Crystal data

C17H18N4O5·0.47CH4O M = 373.40 Orthorhombic, a = 9.4470 (7) Å b = 17.5850 (9) Å c = 22.8714 (12) Å V = 3799.5 (4) Å3 Z = 8 Mo Kα radiation μ = 0.10 mm−1 T = 293 K 0.1 × 0.08 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer 9573 measured reflections 862 independent reflections 658 reflections with I > 2σ(I) R int = 0.105 2 standard reflections every 120 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.111 S = 1.25 862 reflections 146 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.17 e Å−3 Δρmin = −0.19 e Å−3 Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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, 2012 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814004802/gk2603sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004802/gk2603Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814004802/gk2603Isup3.cml CCDC reference: 989432 Additional supporting information: crystallographic information; 3D view; checkCIF report

C₁₇H₁₈N₄O₅·0.47CH₄O	F(000) = 1571.4
M_r = 373.40	D_x = 1.306 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 25 reflections
a = 9.4470 (7) Å	θ = 11–15°
b = 17.5850 (9) Å	µ = 0.10 mm⁻¹
c = 22.8714 (12) Å	T = 293 K
V = 3799.5 (4) Å³	Prismatic, colorless
Z = 8	0.1 × 0.08 × 0.05 mm

Enraf–Nonius CAD-4 diffractometer	R_int = 0.105
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 2.6°
Graphite monochromator	h = −11→11
non–profiled ω/2θ scans	k = −1→20
9573 measured reflections	l = −27→27
862 independent reflections	2 standard reflections every 120 min
658 reflections with I > 2σ(I)	intensity decay: 2%

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.25	w = 1/[σ²(F_o²) + (0.0306P)² + 5.2614P] where P = (F_o² + 2F_c²)/3
862 reflections	(Δ/σ)_max < 0.001
146 parameters	Δρ_max = 0.17 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	Occ. (<1)
O1	0.6805 (4)	0.1635 (2)	0.02775 (15)	0.0559 (10)
O2	1.0000	0.0000	0.0525 (2)	0.0641 (14)
O3	0.4920 (4)	0.2637 (2)	−0.00424 (17)	0.0680 (12)
N1	0.8123 (4)	0.0896 (2)	0.11591 (18)	0.0471 (10)
N2	0.9127 (5)	0.0436 (2)	0.1418 (2)	0.0533 (11)
C1	0.6048 (5)	0.1974 (3)	0.0728 (2)	0.0459 (12)
C2	0.5016 (5)	0.2512 (3)	0.0560 (2)	0.0512 (13)
C3	0.4200 (5)	0.2864 (3)	0.0996 (3)	0.0567 (14)
H3	0.3505	0.3211	0.0888	0.068*
C4	0.4409 (5)	0.2704 (3)	0.1594 (3)	0.0595 (15)
H4	0.3856	0.2946	0.1874	0.071*
C5	0.5434 (5)	0.2189 (3)	0.1765 (2)	0.0528 (13)
H5	0.5580	0.2087	0.2159	0.063*
C6	0.6269 (5)	0.1813 (3)	0.1329 (2)	0.0423 (11)
C7	0.7364 (5)	0.1284 (3)	0.1531 (2)	0.0459 (12)
H7	0.7519	0.1223	0.1930	0.055*
C8	1.0000	0.0000	0.1068 (3)	0.0467 (17)
C9	0.4052 (7)	0.3261 (4)	−0.0244 (3)	0.0779 (19)
H9A	0.4081	0.3283	−0.0663	0.117*
H9B	0.4405	0.3729	−0.0086	0.117*
H9C	0.3093	0.3185	−0.0118	0.117*
O4	0.579 (2)	0.1913 (12)	0.3182 (9)	0.098 (9)	0.234 (11)
H1M	0.5601	0.1599	0.3453	0.148*	0.234 (11)
C10	0.703 (3)	0.2337 (18)	0.3207 (10)	0.075 (10)	0.234 (11)
H10A	0.7221	0.2638	0.3554	0.113*	0.234 (11)
H10B	0.7221	0.2638	0.2861	0.113*	0.234 (11)
H10C	0.7632	0.1890	0.3207	0.113*	0.234 (11)
H1O	0.743 (5)	0.134 (3)	0.048 (2)	0.057 (15)*
H2N	0.916 (5)	0.040 (3)	0.183 (3)	0.052 (15)*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.062 (2)	0.055 (2)	0.051 (2)	0.0187 (18)	−0.0048 (18)	−0.0067 (17)
O2	0.077 (4)	0.069 (3)	0.047 (3)	0.019 (3)	0.000	0.000
O3	0.076 (3)	0.063 (2)	0.066 (3)	0.026 (2)	−0.0196 (19)	−0.001 (2)
N1	0.043 (2)	0.045 (2)	0.053 (2)	0.004 (2)	−0.0026 (19)	0.0038 (19)
N2	0.054 (3)	0.059 (2)	0.047 (3)	0.020 (2)	−0.001 (2)	0.004 (2)
C1	0.038 (3)	0.044 (2)	0.056 (3)	0.000 (2)	−0.002 (2)	−0.005 (2)
C2	0.046 (3)	0.042 (2)	0.065 (3)	0.004 (2)	−0.010 (3)	0.001 (3)
C3	0.039 (3)	0.049 (3)	0.082 (4)	0.006 (2)	−0.001 (3)	−0.005 (3)
C4	0.047 (3)	0.052 (3)	0.080 (4)	0.002 (3)	0.017 (3)	−0.008 (3)
C5	0.046 (3)	0.053 (3)	0.059 (3)	−0.002 (2)	0.014 (2)	0.002 (3)
C6	0.039 (3)	0.035 (2)	0.052 (3)	−0.001 (2)	0.004 (2)	−0.002 (2)
C7	0.047 (3)	0.044 (3)	0.046 (3)	−0.001 (2)	0.000 (2)	0.006 (2)
C8	0.047 (4)	0.040 (4)	0.053 (5)	0.003 (3)	0.000	0.000
C9	0.082 (4)	0.058 (3)	0.094 (5)	0.015 (3)	−0.025 (4)	0.014 (3)
O4	0.117 (19)	0.087 (15)	0.091 (17)	0.004 (12)	0.030 (13)	0.010 (12)
C10	0.07 (2)	0.10 (3)	0.057 (16)	0.021 (19)	−0.001 (11)	−0.018 (15)

O1—C1	1.389 (6)	C4—H4	0.9300
O1—H1O	0.91 (5)	C5—C6	1.433 (7)
O2—C8	1.243 (8)	C5—H5	0.9300
O3—C2	1.397 (6)	C6—C7	1.466 (6)
O3—C9	1.445 (6)	C7—H7	0.9300
N1—C7	1.305 (6)	C8—N2ⁱ	1.381 (6)
N1—N2	1.381 (5)	C9—H9A	0.9600
N2—C8	1.381 (6)	C9—H9B	0.9600
N2—H2N	0.94 (6)	C9—H9C	0.9600
C1—C2	1.413 (6)	O4—C10	1.39 (3)
C1—C6	1.418 (7)	O4—H1M	0.8500
C2—C3	1.405 (8)	C10—C10ⁱⁱ	1.06 (5)
C3—C4	1.411 (8)	C10—H10A	0.9700
C3—H3	0.9300	C10—H10B	0.9700
C4—C5	1.382 (7)	C10—H10C	0.9700

C1—O1—H1O	102 (3)	N1—C7—C6	121.0 (4)
C2—O3—C9	118.1 (4)	N1—C7—H7	119.5
C7—N1—N2	113.9 (4)	C6—C7—H7	119.5
N1—N2—C8	119.1 (5)	O2—C8—N2	125.4 (3)
N1—N2—H2N	120 (3)	O2—C8—N2ⁱ	125.4 (3)
C8—N2—H2N	121 (3)	N2—C8—N2ⁱ	109.2 (7)
O1—C1—C2	116.1 (5)	O3—C9—H9A	109.5
O1—C1—C6	123.9 (4)	O3—C9—H9B	109.5
C2—C1—C6	120.0 (5)	H9A—C9—H9B	109.5
O3—C2—C3	126.5 (5)	O3—C9—H9C	109.5
O3—C2—C1	114.8 (5)	H9A—C9—H9C	109.5
C3—C2—C1	118.7 (5)	H9B—C9—H9C	109.5
C2—C3—C4	121.7 (5)	C10—O4—H1M	119.9
C2—C3—H3	119.2	C10ⁱⁱ—C10—O4	177.6 (17)
C4—C3—H3	119.2	C10ⁱⁱ—C10—H10A	63.1
C5—C4—C3	120.2 (5)	O4—C10—H10A	118.9
C5—C4—H4	119.9	C10ⁱⁱ—C10—H10B	63.1
C3—C4—H4	119.9	O4—C10—H10B	114.5
C4—C5—C6	119.4 (5)	H10A—C10—H10B	109.6
C4—C5—H5	120.3	C10ⁱⁱ—C10—H10C	87.1
C6—C5—H5	120.3	O4—C10—H10C	93.3
C1—C6—C5	120.1 (4)	H10A—C10—H10C	109.6
C1—C6—C7	122.3 (4)	H10B—C10—H10C	109.6
C5—C6—C7	117.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1	0.91 (5)	1.86 (5)	2.703 (5)	152 (5)
N2—H2N···O3ⁱⁱⁱ	0.94 (6)	2.38 (5)	3.044 (6)	128 (4)
N2—H2N···O1ⁱⁱⁱ	0.94 (6)	2.33 (6)	3.204 (6)	155 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N1	0.91 (5)	1.86 (5)	2.703 (5)	152 (5)
N2—H2N⋯O3ⁱ	0.94 (6)	2.38 (5)	3.044 (6)	128 (4)
N2—H2N⋯O1ⁱ	0.94 (6)	2.33 (6)	3.204 (6)	155 (4)

Symmetry code: (i) .

5 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. Antimicrobial and mutagenic activity of some carbono- and thiocarbonohydrazone ligands and their copper(II), iron(II) and zinc(II) complexes.

Authors: A Bacchi; M Carcelli; P Pelagatti; C Pelizzi; G Pelizzi; F Zani
Journal: J Inorg Biochem Date: 1999-06-15 Impact factor: 4.155