Literature DB >> 22347029

N'-[(E)-2-Hy-droxy-5-iodo-benzyl-idene]furan-2-carbohydrazide monohydrate.

Rahman Bikas, Parisa Mahboubi Anarjan, Seik Weng Ng, Edward R T Tiekink.

Abstract

The organic mol-ecule of the title monohydrate, C(12)H(9)IN(2)O(3)·H(2)O, features a n class="Disease">disordered furyl ring with the major component [site occupancy = 0.575 (18)] having the carbonyl O and furyl O atoms syn, and the other conformation having these atoms anti. The mol-ecule is slightly twisted with the dihedral angle between the benzene and furyl rings being 10.3 (6)° (major component). An intra-molecular O-H⋯N(imine) hydrogen bond is formed. In the crystal, the water mol-ecule accepts a hydrogen bond from an amine H atom, and forms two O-H⋯O(carbon-yl) hydrogen bonds, thereby linking three different carbohydrazide mol-ecules. The result is a supra-molecular layer parallel to (001). The closest contacts between layers are of the type I⋯I, at a distance of 3.6986 (6) Å.

Entities: Chemical Disease Gene Species

Year: 2012 PMID： 22347029 PMCID： PMC3275173 DOI： 10.1107/S1600536811055826

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

Related literature

For historical background to aroylhydrazones, see: Craliz et al. (1955 ▶). For the structure of the isomorphous n class="Chemical">bromido derivative, see: Tai et al. (2007 ▶). For the structures of related carbohydrazides, see: Abdel-Aziz et al. (2011 ▶); Bikas et al. (2012 ▶). For the synthesis of a precursor molecule, see: Nielsen & Gothelf (2001 ▶).

Experimental

Crystal data

C12H9IN2O3·n class="Chemical">H2O M = 374.13 Orthorhombic, a = 4.8607 (2) Å b = 12.5873 (4) Å c = 21.1627 (9) Å V = 1294.80 (9) Å3 Z = 4 Cu Kα radiation μ = 19.57 mm−1 T = 100 K 0.20 × 0.08 × 0.04 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.111, T max = 0.508 4758 measured reflections 2641 independent reflections 2575 reflections with I > 2σ(I) R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.059 wR(F 2) = 0.158 S = 1.09 2641 reflections 186 parameters 34 restraints H-atom parameters constrained Δρmax = 3.22 e Å−3 Δρmin = −1.82 e Å−3 Absolute structure: Flack (1983 ▶), 1050 Friedel pairs Flack parameter: −0.020 (12) Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811055826/hb6573sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055826/hb6573Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811055826/hb6573Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₂H₉IN₂O₃·H₂O	F(000) = 728
M_r = 374.13	D_x = 1.919 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2924 reflections
a = 4.8607 (2) Å	θ = 4.1–76.3°
b = 12.5873 (4) Å	µ = 19.57 mm⁻¹
c = 21.1627 (9) Å	T = 100 K
V = 1294.80 (9) Å³	Prism, colourless
Z = 4	0.20 × 0.08 × 0.04 mm

Agilent SuperNova Dual diffractometer with an Atlas detector	2641 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2575 reflections with I > 2σ(I)
Mirror	R_int = 0.039
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.5°, θ_min = 4.1°
ω scan	h = −6→5
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −15→10
T_min = 0.111, T_max = 0.508	l = −18→26
4758 measured reflections

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.059	H-atom parameters constrained
wR(F²) = 0.158	w = 1/[σ²(F_o²) + (0.127P)²] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
2641 reflections	Δρ_max = 3.22 e Å⁻³
186 parameters	Δρ_min = −1.82 e Å⁻³
34 restraints	Absolute structure: Flack (1983), 1050 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.020 (12)

	x	y	z	U_iso*/U_eq	Occ. (<1)
I1	1.44774 (10)	1.14557 (3)	0.97807 (2)	0.0213 (2)
O1	0.7447 (14)	0.7625 (4)	0.8846 (3)	0.0239 (12)
H1	0.7161	0.7655	0.8455	0.036*
O2	0.1609 (12)	0.7779 (4)	0.7326 (3)	0.0205 (10)
O3	−0.214 (2)	0.8642 (7)	0.6509 (4)	0.016 (2)	0.575 (18)
O3'	−0.043 (3)	1.0345 (7)	0.6855 (7)	0.016*	0.425 (18)
O1W	0.3405 (13)	1.1654 (4)	0.7575 (3)	0.0265 (12)
H11	0.4756	1.2055	0.7641	0.040*
H12	0.1948	1.1982	0.7664	0.040*
N1	0.5129 (13)	0.9031 (5)	0.8010 (3)	0.0170 (12)
N2	0.3308 (13)	0.9420 (4)	0.7566 (3)	0.0158 (11)
H2	0.3265	1.0105	0.7483	0.019*
C1	0.8927 (16)	0.8472 (6)	0.9027 (3)	0.0196 (14)
C2	1.0829 (17)	0.8331 (6)	0.9520 (4)	0.0222 (14)
H2A	1.1050	0.7648	0.9704	0.027*
C3	1.2403 (16)	0.9185 (6)	0.9745 (3)	0.0196 (14)
H3	1.3645	0.9086	1.0087	0.024*
C4	1.2132 (15)	1.0178 (6)	0.9464 (3)	0.0168 (13)
C5	1.0320 (17)	1.0338 (5)	0.8971 (3)	0.0176 (13)
H5	1.0188	1.1018	0.8779	0.021*
C6	0.8665 (15)	0.9496 (6)	0.8753 (3)	0.0165 (13)
C7	0.6706 (16)	0.9737 (6)	0.8255 (3)	0.0168 (13)
H7	0.6588	1.0447	0.8105	0.020*
C8	0.1574 (17)	0.8747 (6)	0.7254 (3)	0.0184 (13)
C9	−0.0322 (15)	0.9270 (5)	0.6827 (3)	0.0166 (13)
C10	−0.085 (3)	1.0323 (8)	0.6628 (8)	0.024 (3)	0.575 (18)
H10	0.0141	1.0934	0.6761	0.028*	0.575 (18)
C10'	−0.226 (5)	0.8865 (16)	0.6390 (12)	0.024*	0.425 (18)
H10'	−0.2631	0.8141	0.6297	0.028*	0.425 (18)
C11	−0.298 (3)	1.0318 (11)	0.6217 (7)	0.021 (3)	0.575 (18)
H11A	−0.3751	1.0920	0.6012	0.025*	0.575 (18)
C11'	−0.345 (4)	0.9727 (17)	0.6138 (9)	0.021*	0.425 (18)
H11'	−0.4821	0.9720	0.5819	0.025*	0.425 (18)
C12	−0.384 (3)	0.9257 (11)	0.6150 (5)	0.018 (3)	0.575 (18)
H12A	−0.5336	0.9012	0.5901	0.022*	0.575 (18)
C12'	−0.233 (4)	1.0650 (16)	0.6422 (9)	0.018*	0.425 (18)
H12'	−0.2832	1.1362	0.6325	0.022*	0.425 (18)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0259 (3)	0.0187 (3)	0.0192 (3)	0.00161 (17)	−0.00272 (17)	−0.00437 (15)
O1	0.036 (3)	0.015 (2)	0.021 (3)	−0.005 (2)	−0.005 (2)	0.002 (2)
O2	0.022 (2)	0.013 (2)	0.026 (3)	0.002 (2)	−0.001 (2)	−0.0006 (19)
O3	0.023 (4)	0.018 (4)	0.006 (4)	0.004 (4)	−0.006 (3)	−0.004 (3)
O1W	0.027 (3)	0.013 (2)	0.039 (3)	−0.001 (2)	−0.002 (3)	−0.004 (2)
N1	0.023 (3)	0.017 (2)	0.012 (2)	0.002 (2)	0.001 (2)	−0.001 (2)
N2	0.022 (3)	0.010 (2)	0.015 (2)	0.001 (2)	−0.003 (2)	−0.001 (2)
C1	0.024 (4)	0.019 (3)	0.016 (3)	−0.002 (3)	0.001 (3)	0.000 (3)
C2	0.032 (4)	0.016 (3)	0.019 (3)	0.000 (3)	−0.004 (3)	0.003 (3)
C3	0.023 (3)	0.024 (4)	0.012 (3)	0.000 (3)	−0.004 (3)	0.003 (3)
C4	0.021 (3)	0.014 (3)	0.015 (3)	−0.002 (3)	0.001 (3)	−0.006 (2)
C5	0.026 (3)	0.014 (3)	0.012 (3)	0.001 (3)	0.000 (3)	−0.002 (2)
C6	0.016 (3)	0.017 (3)	0.016 (3)	0.003 (3)	0.000 (3)	0.001 (2)
C7	0.021 (3)	0.016 (3)	0.013 (3)	0.002 (3)	0.001 (3)	0.001 (2)
C8	0.020 (3)	0.020 (3)	0.015 (3)	0.003 (3)	0.001 (3)	−0.002 (3)
C9	0.021 (3)	0.014 (3)	0.015 (3)	0.003 (3)	0.001 (3)	−0.005 (2)
C10	0.031 (7)	0.019 (5)	0.020 (6)	0.000 (5)	−0.007 (6)	−0.003 (5)
C11	0.025 (6)	0.018 (6)	0.021 (6)	0.005 (5)	−0.002 (5)	0.005 (5)
C12	0.029 (6)	0.019 (6)	0.007 (4)	−0.003 (5)	−0.007 (4)	0.000 (4)

I1—C4	2.082 (7)	C3—H3	0.9500
O1—C1	1.342 (9)	C4—C5	1.379 (10)
O1—H1	0.8400	C5—C6	1.409 (11)
O2—C8	1.228 (9)	C5—H5	0.9500
O3—C9	1.363 (8)	C6—C7	1.451 (10)
O3—C12	1.363 (9)	C7—H7	0.9500
O3'—C9	1.355 (8)	C8—C9	1.449 (10)
O3'—C12'	1.358 (9)	C9—C10	1.413 (9)
O1W—H11	0.8402	C9—C10'	1.413 (10)
O1W—H12	0.8409	C10—C11	1.353 (9)
N1—C7	1.283 (10)	C10—H10	0.9500
N1—N2	1.381 (8)	C10'—C11'	1.341 (10)
N2—C8	1.365 (10)	C10'—H10'	0.9500
N2—H2	0.8800	C11—C12	1.407 (9)
C1—C2	1.406 (10)	C11—H11A	0.9500
C1—C6	1.418 (10)	C11'—C12'	1.415 (10)
C2—C3	1.402 (10)	C11'—H11'	0.9500
C2—H2A	0.9500	C12—H12A	0.9500
C3—C4	1.391 (9)	C12'—H12'	0.9500

C1—O1—H1	109.5	C6—C7—H7	118.6
C9—O3—C12	109.8 (8)	O2—C8—N2	123.1 (7)
C9—O3'—C12'	106.2 (12)	O2—C8—C9	122.5 (7)
H11—O1W—H12	109.0	N2—C8—C9	114.4 (6)
C7—N1—N2	114.4 (6)	O3—C9—C10	106.3 (8)
C8—N2—N1	120.4 (6)	O3'—C9—C10'	111.3 (11)
C8—N2—H2	119.8	O3'—C9—C8	116.8 (8)
N1—N2—H2	119.8	O3—C9—C8	117.1 (6)
O1—C1—C2	117.6 (6)	C10—C9—C8	136.6 (8)
O1—C1—C6	123.9 (7)	C10'—C9—C8	131.8 (10)
C2—C1—C6	118.5 (7)	C11—C10—C9	109.0 (9)
C3—C2—C1	120.9 (6)	C11—C10—H10	125.5
C3—C2—H2A	119.5	C9—C10—H10	125.5
C1—C2—H2A	119.5	C11'—C10'—C9	104.7 (14)
C4—C3—C2	119.5 (7)	C11'—C10'—H10'	127.6
C4—C3—H3	120.3	C9—C10'—H10'	127.6
C2—C3—H3	120.3	C10—C11—C12	107.2 (10)
C5—C4—C3	121.0 (6)	C10—C11—H11A	126.4
C5—C4—I1	118.7 (5)	C12—C11—H11A	126.4
C3—C4—I1	120.3 (5)	C10'—C11'—C12'	109.3 (16)
C4—C5—C6	120.2 (6)	C10'—C11'—H11'	125.3
C4—C5—H5	119.9	C12'—C11'—H11'	125.3
C6—C5—H5	119.9	O3—C12—C11	107.6 (9)
C5—C6—C1	119.9 (7)	O3—C12—H12A	126.2
C5—C6—C7	117.1 (6)	C11—C12—H12A	126.2
C1—C6—C7	123.0 (7)	O3'—C12'—C11'	108.3 (15)
N1—C7—C6	122.7 (6)	O3'—C12'—H12'	125.8
N1—C7—H7	118.6	C11'—C12'—H12'	125.8

C7—N1—N2—C8	177.9 (6)	C12—O3—C9—C10'	−21 (6)
O1—C1—C2—C3	−178.5 (7)	C12—O3—C9—C8	177.4 (9)
C6—C1—C2—C3	1.0 (11)	O2—C8—C9—O3'	170.8 (9)
C1—C2—C3—C4	−1.8 (12)	N2—C8—C9—O3'	−9.3 (11)
C2—C3—C4—C5	0.6 (11)	O2—C8—C9—O3	1.1 (12)
C2—C3—C4—I1	−179.3 (6)	N2—C8—C9—O3	−179.0 (8)
C3—C4—C5—C6	1.3 (11)	O2—C8—C9—C10	−178.1 (12)
I1—C4—C5—C6	−178.8 (5)	N2—C8—C9—C10	1.8 (16)
C4—C5—C6—C1	−2.0 (11)	O2—C8—C9—C10'	−5(2)
C4—C5—C6—C7	176.9 (7)	N2—C8—C9—C10'	174.5 (19)
O1—C1—C6—C5	−179.6 (7)	O3'—C9—C10—C11	−151 (3)
C2—C1—C6—C5	0.8 (11)	O3—C9—C10—C11	1.9 (15)
O1—C1—C6—C7	1.6 (12)	C10'—C9—C10—C11	6.6 (18)
C2—C1—C6—C7	−178.0 (7)	C8—C9—C10—C11	−178.8 (10)
N2—N1—C7—C6	176.9 (6)	O3'—C9—C10'—C11'	3(3)
C5—C6—C7—N1	178.6 (7)	O3—C9—C10'—C11'	157 (8)
C1—C6—C7—N1	−2.6 (11)	C10—C9—C10'—C11'	−6(2)
N1—N2—C8—O2	−3.3 (11)	C8—C9—C10'—C11'	179.0 (13)
N1—N2—C8—C9	176.8 (6)	C9—C10—C11—C12	0.0 (17)
C12'—O3'—C9—O3	−10.9 (17)	C9—C10'—C11'—C12'	−1(3)
C12'—O3'—C9—C10	21 (2)	C9—O3—C12—C11	3.2 (14)
C12'—O3'—C9—C10'	−3(2)	C10—C11—C12—O3	−1.9 (16)
C12'—O3'—C9—C8	−179.6 (11)	C9—O3'—C12'—C11'	1.6 (19)
C12—O3—C9—O3'	8.7 (15)	C10'—C11'—C12'—O3'	0(3)
C12—O3—C9—C10	−3.1 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1w	0.88	1.96	2.813 (7)	163
O1—H1···N1	0.84	2.20	2.744 (8)	122
O1w—H11···O2ⁱ	0.84	1.99	2.815 (8)	167
O1w—H12···O2ⁱⁱ	0.84	2.00	2.826 (8)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1w	0.88	1.96	2.813 (7)	163
O1—H1⋯N1	0.84	2.20	2.744 (8)	122
O1w—H11⋯O2ⁱ	0.84	1.99	2.815 (8)	167
O1w—H12⋯O2ⁱⁱ	0.84	2.00	2.826 (8)	168

Symmetry codes: (i) ; (ii) .

4 in total

1. Mode of action of isonicotinic hydrazide.

Authors: J CYMERMAN-CRAIG; D WILLIS; S D RUBBO; J EDGAR
Journal: Nature Date: 1955-07-02 Impact factor: 49.962

2. A short history of SHELX.

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

3. 2-[((E)-2-{2-[(E)-2-Hy-droxy-benzyl-idene]hydrazinecarbon-yl}hydrazinyl-idene)meth-yl]phenol.

Authors: Rahman Bikas; Parisa Mahboubi Anarjan; Seik Weng Ng; Edward R T Tiekink
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-12-21

4. N'-[(1E,2E)-1-(2-Phenyl-hydrazin-1-yl-idene)-1-(phenyl-sulfon-yl)propan-2-yl-idene]benzohydrazide.

Authors: Hatem A Abdel-Aziz; Seik Weng Ng; Edward R T Tiekink
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-08-11