Literature DB >> 21578524

1,5-Bis[(E)-1-(2-hydroxy-phen-yl)ethyl-idene]carbonohydrazide dimethyl sulfoxide solvate.

Julio Zukerman-Schpector, Md Abu Affan, Siong Wan Foo, Edward R T Tiekink.

Abstract

The title dimethyl sulfoxide (n class="Chemical">DMSO) solvate, C(17)H(18)N(4)O(3)·C(2)H(6)OS, shows the disubstituted urea derivative to adopt an almost planar geometry (r.m.s. deviation for non-H atoms = 0.132 Å); the mol-ecule has non-crystallographic twofold mol-ecular symmetry. This conformation is stabilized by two intra-molecular O-H⋯N hydrogen bonds. The components of the crystal are connected by N-H⋯O hydrogen bonds, whereby both amine H atoms are connected to a DMSO O atom, and C-H⋯O contacts involving the DMSO H and urea carbonyl atoms, forming a supra-molecular chain along the c axis. The chains associate via C-H⋯π inter-actions.

Entities: CellLine Chemical Disease Gene

Year: 2009 PMID： 21578524 PMCID： PMC2971043 DOI： 10.1107/S1600536809044985

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

Related literature

For background and recent studies on the biological activity of tin/organotin compounds, see: Gielen & Tiekink (2005 ▶); Affan et al. (2009 ▶).

Experimental

Crystal data

C17H18N4O3·C2H6OS M = 404.48 Monoclinic, a = 15.3260 (19) Å b = 7.1248 (7) Å c = 18.439 (2) Å β = 102.724 (2)° V = 1964.0 (4) Å3 Z = 4 Mo Kα radiation μ = 0.20 mm−1 T = 153 K 0.32 × 0.30 × 0.15 mm

Data collection

Rigaku Saturn724 diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.661, T max = 1.000 21771 measured reflections 4493 independent reflections 4369 reflections with I > 2σ(I) R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.110 S = 1.08 4493 reflections 269 parameters 4 restraints H-atom parameters constrained Δρmax = 0.32 e Å−3 Δρmin = −0.32 e Å−3 Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks general, I. DOI: 10.1107/S1600536809044985/hb5198sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044985/hb5198Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₇H₁₈N₄O₃·C₂H₆OS	F(000) = 856
M_r = 404.48	D_x = 1.368 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6256 reflections
a = 15.3260 (19) Å	θ = 2.7–30.3°
b = 7.1248 (7) Å	µ = 0.20 mm⁻¹
c = 18.439 (2) Å	T = 153 K
β = 102.724 (2)°	Prism, colourless
V = 1964.0 (4) Å³	0.32 × 0.30 × 0.15 mm
Z = 4

Rigaku Saturn724 diffractometer	4493 independent reflections
Radiation source: sealed tube	4369 reflections with I > 2σ(I)
graphite	R_int = 0.030
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.5°, θ_min = 2.3°
ω scans	h = −19→18
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −9→9
T_min = 0.661, T_max = 1.000	l = −23→23
21771 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0572P)² + 0.8148P] where P = (F_o² + 2F_c²)/3
4493 reflections	(Δ/σ)_max = 0.001
269 parameters	Δρ_max = 0.32 e Å⁻³
4 restraints	Δρ_min = −0.32 e Å⁻³

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.31503 (7)	−0.00388 (17)	0.72741 (5)	0.0315 (2)
H1O	0.2776	0.0352	0.6901	0.047*
O2	0.08573 (6)	0.17694 (15)	0.63438 (5)	0.0258 (2)
O3	−0.14836 (6)	0.29124 (14)	0.62863 (5)	0.0248 (2)
H3O	−0.1046	0.27566	0.6087	0.037*
N1	0.24627 (7)	0.12659 (16)	0.59756 (6)	0.0207 (2)
N2	0.17027 (7)	0.17151 (17)	0.54592 (6)	0.0221 (2)
H2N	0.1683	0.1867	0.4982	0.026*
N3	0.02270 (7)	0.24035 (16)	0.51181 (6)	0.0221 (2)
H3N	0.0339	0.2475	0.4671	0.027*
N4	−0.05924 (7)	0.26766 (15)	0.52770 (6)	0.0204 (2)
C1	0.39368 (9)	0.00078 (19)	0.70500 (8)	0.0233 (3)
C2	0.47033 (10)	−0.0498 (2)	0.75744 (8)	0.0289 (3)
H2	0.4655	−0.0855	0.8060	0.035*
C3	0.55316 (10)	−0.0486 (2)	0.73960 (9)	0.0306 (3)
H3	0.6050	−0.0826	0.7759	0.037*
C4	0.56065 (9)	0.0023 (2)	0.66867 (9)	0.0304 (3)
H4	0.6176	0.0036	0.6562	0.037*
C5	0.48487 (9)	0.0513 (2)	0.61617 (8)	0.0259 (3)
H5	0.4907	0.0848	0.5676	0.031*
C6	0.39962 (8)	0.05313 (17)	0.63249 (7)	0.0200 (2)
C7	0.31992 (8)	0.10518 (17)	0.57510 (7)	0.0195 (2)
C8	0.32461 (9)	0.1268 (2)	0.49519 (7)	0.0256 (3)
H8A	0.2859	0.0332	0.4651	0.038*
H8B	0.3864	0.1082	0.4903	0.038*
H8C	0.3046	0.2530	0.4780	0.038*
C9	0.09245 (8)	0.19450 (18)	0.56997 (7)	0.0202 (3)
C10	−0.12715 (8)	0.30637 (18)	0.47447 (7)	0.0199 (3)
C11	−0.12059 (9)	0.3222 (2)	0.39461 (7)	0.0278 (3)
H11A	−0.0659	0.3903	0.3917	0.042*
H11B	−0.1727	0.3904	0.3665	0.042*
H11C	−0.1189	0.1964	0.3735	0.042*
C12	−0.21323 (8)	0.33360 (17)	0.49676 (7)	0.0193 (2)
C13	−0.21935 (9)	0.32848 (18)	0.57248 (7)	0.0213 (3)
C14	−0.30117 (9)	0.36037 (19)	0.59185 (8)	0.0253 (3)
H14	−0.3042	0.3618	0.6428	0.030*
C15	−0.37788 (9)	0.3899 (2)	0.53742 (9)	0.0282 (3)
H15	−0.4333	0.4109	0.5512	0.034*
C16	−0.37441 (9)	0.3891 (2)	0.46264 (8)	0.0277 (3)
H16	−0.4274	0.4061	0.4253	0.033*
C17	−0.29285 (9)	0.36309 (19)	0.44331 (8)	0.0240 (3)
H17	−0.2907	0.3653	0.3922	0.029*
S1	0.88984 (2)	0.73077 (5)	0.686182 (17)	0.02070 (11)
O4	0.88705 (7)	0.75110 (16)	0.60411 (5)	0.0286 (2)
C18	0.79058 (9)	0.8403 (2)	0.70127 (8)	0.0286 (3)
H18A	0.7859	0.9673	0.6804	0.043*
H18B	0.7930	0.8470	0.7548	0.043*
H18C	0.7383	0.7666	0.6769	0.043*
C19	0.96707 (9)	0.9044 (2)	0.73080 (7)	0.0258 (3)
H19A	1.0273	0.8722	0.7250	0.039*
H19B	0.9664	0.9093	0.7838	0.039*
H19C	0.9499	1.0271	0.7081	0.039*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0242 (5)	0.0477 (6)	0.0232 (5)	0.0023 (5)	0.0068 (4)	0.0100 (4)
O2	0.0235 (5)	0.0351 (5)	0.0197 (4)	0.0028 (4)	0.0067 (4)	0.0018 (4)
O3	0.0235 (5)	0.0322 (5)	0.0190 (5)	0.0008 (4)	0.0053 (4)	0.0004 (4)
N1	0.0187 (5)	0.0233 (5)	0.0197 (5)	0.0011 (4)	0.0030 (4)	0.0000 (4)
N2	0.0183 (5)	0.0312 (6)	0.0165 (5)	0.0013 (4)	0.0033 (4)	0.0017 (4)
N3	0.0179 (5)	0.0305 (6)	0.0190 (5)	0.0015 (4)	0.0062 (4)	0.0013 (4)
N4	0.0177 (5)	0.0226 (5)	0.0219 (5)	0.0000 (4)	0.0065 (4)	−0.0004 (4)
C1	0.0229 (6)	0.0222 (6)	0.0247 (6)	−0.0002 (5)	0.0051 (5)	0.0021 (5)
C2	0.0289 (7)	0.0282 (7)	0.0276 (7)	−0.0007 (6)	0.0017 (5)	0.0078 (6)
C3	0.0241 (7)	0.0268 (7)	0.0367 (8)	0.0028 (6)	−0.0026 (6)	0.0054 (6)
C4	0.0204 (6)	0.0315 (7)	0.0392 (8)	0.0020 (6)	0.0062 (6)	0.0000 (6)
C5	0.0224 (6)	0.0287 (7)	0.0272 (7)	−0.0001 (5)	0.0065 (5)	−0.0016 (5)
C6	0.0193 (6)	0.0188 (6)	0.0216 (6)	−0.0002 (5)	0.0039 (5)	−0.0014 (5)
C7	0.0210 (6)	0.0190 (6)	0.0191 (6)	−0.0007 (5)	0.0058 (5)	−0.0016 (4)
C8	0.0241 (6)	0.0342 (7)	0.0194 (6)	0.0016 (5)	0.0064 (5)	0.0000 (5)
C9	0.0205 (6)	0.0200 (6)	0.0204 (6)	−0.0010 (5)	0.0049 (5)	−0.0004 (5)
C10	0.0212 (6)	0.0183 (6)	0.0204 (6)	−0.0014 (5)	0.0054 (5)	−0.0007 (5)
C11	0.0242 (6)	0.0390 (8)	0.0210 (6)	0.0024 (6)	0.0067 (5)	0.0027 (6)
C12	0.0190 (6)	0.0174 (5)	0.0217 (6)	−0.0012 (5)	0.0051 (5)	−0.0010 (5)
C13	0.0225 (6)	0.0182 (6)	0.0238 (6)	−0.0022 (5)	0.0062 (5)	−0.0011 (5)
C14	0.0277 (7)	0.0238 (6)	0.0276 (6)	−0.0011 (5)	0.0129 (5)	−0.0018 (5)
C15	0.0213 (6)	0.0269 (7)	0.0395 (8)	0.0004 (5)	0.0130 (6)	−0.0019 (6)
C16	0.0198 (6)	0.0289 (7)	0.0328 (7)	0.0016 (5)	0.0024 (5)	0.0000 (6)
C17	0.0232 (6)	0.0242 (6)	0.0242 (6)	−0.0003 (5)	0.0042 (5)	−0.0012 (5)
S1	0.01945 (17)	0.02472 (18)	0.01720 (17)	0.00048 (11)	0.00244 (12)	−0.00063 (11)
O4	0.0223 (5)	0.0470 (6)	0.0162 (5)	0.0010 (4)	0.0034 (4)	−0.0024 (4)
C18	0.0214 (6)	0.0409 (8)	0.0241 (6)	0.0025 (6)	0.0060 (5)	−0.0001 (6)
C19	0.0239 (6)	0.0318 (7)	0.0206 (6)	−0.0056 (5)	0.0027 (5)	−0.0006 (5)

O1—C1	1.3580 (16)	C8—H8B	0.9800
O1—H1O	0.8401	C8—H8C	0.9800
O2—C9	1.2210 (16)	C10—C12	1.4785 (17)
O3—C13	1.3528 (16)	C10—C11	1.5021 (17)
O3—H3O	0.8400	C11—H11A	0.9800
N1—C7	1.2942 (16)	C11—H11B	0.9800
N1—N2	1.3700 (15)	C11—H11C	0.9800
N2—C9	1.3707 (16)	C12—C17	1.4053 (18)
N2—H2N	0.8799	C12—C13	1.4202 (17)
N3—N4	1.3648 (15)	C13—C14	1.3961 (18)
N3—C9	1.3764 (17)	C14—C15	1.383 (2)
N3—H3N	0.8799	C14—H14	0.9500
N4—C10	1.2933 (17)	C15—C16	1.392 (2)
C1—C2	1.3944 (19)	C15—H15	0.9500
C1—C6	1.4103 (18)	C16—C17	1.3856 (19)
C2—C3	1.380 (2)	C16—H16	0.9500
C2—H2	0.9500	C17—H17	0.9500
C3—C4	1.386 (2)	S1—O4	1.5115 (10)
C3—H3	0.9500	S1—C19	1.7830 (14)
C4—C5	1.383 (2)	S1—C18	1.7852 (14)
C4—H4	0.9500	C18—H18A	0.9800
C5—C6	1.4039 (18)	C18—H18B	0.9800
C5—H5	0.9500	C18—H18C	0.9800
C6—C7	1.4765 (17)	C19—H19A	0.9800
C7—C8	1.4987 (17)	C19—H19B	0.9800
C8—H8A	0.9800	C19—H19C	0.9800

C1—O1—H1O	103.5	N4—C10—C11	122.93 (11)
C13—O3—H3O	106.0	C12—C10—C11	121.27 (11)
C7—N1—N2	118.23 (11)	C10—C11—H11A	109.5
N1—N2—C9	118.05 (10)	C10—C11—H11B	109.5
N1—N2—H2N	124.1	H11A—C11—H11B	109.5
C9—N2—H2N	117.9	C10—C11—H11C	109.5
N4—N3—C9	117.39 (11)	H11A—C11—H11C	109.5
N4—N3—H3N	124.8	H11B—C11—H11C	109.5
C9—N3—H3N	117.7	C17—C12—C13	117.26 (11)
C10—N4—N3	119.49 (11)	C17—C12—C10	120.98 (11)
O1—C1—C2	116.83 (12)	C13—C12—C10	121.75 (11)
O1—C1—C6	122.81 (11)	O3—C13—C14	116.90 (12)
C2—C1—C6	120.35 (12)	O3—C13—C12	122.77 (11)
C3—C2—C1	120.79 (13)	C14—C13—C12	120.33 (12)
C3—C2—H2	119.6	C15—C14—C13	120.45 (13)
C1—C2—H2	119.6	C15—C14—H14	119.8
C2—C3—C4	119.89 (13)	C13—C14—H14	119.8
C2—C3—H3	120.1	C14—C15—C16	120.42 (12)
C4—C3—H3	120.1	C14—C15—H15	119.8
C5—C4—C3	119.68 (13)	C16—C15—H15	119.8
C5—C4—H4	120.2	C17—C16—C15	119.28 (13)
C3—C4—H4	120.2	C17—C16—H16	120.4
C4—C5—C6	122.01 (13)	C15—C16—H16	120.4
C4—C5—H5	119.0	C16—C17—C12	122.19 (12)
C6—C5—H5	119.0	C16—C17—H17	118.9
C5—C6—C1	117.27 (12)	C12—C17—H17	118.9
C5—C6—C7	120.72 (12)	O4—S1—C19	105.37 (6)
C1—C6—C7	122.01 (11)	O4—S1—C18	106.08 (6)
N1—C7—C6	116.26 (11)	C19—S1—C18	97.28 (7)
N1—C7—C8	122.45 (11)	S1—C18—H18A	109.5
C6—C7—C8	121.28 (11)	S1—C18—H18B	109.5
C7—C8—H8A	109.5	H18A—C18—H18B	109.5
C7—C8—H8B	109.5	S1—C18—H18C	109.5
H8A—C8—H8B	109.5	H18A—C18—H18C	109.5
C7—C8—H8C	109.5	H18B—C18—H18C	109.5
H8A—C8—H8C	109.5	S1—C19—H19A	109.5
H8B—C8—H8C	109.5	S1—C19—H19B	109.5
O2—C9—N2	124.62 (12)	H19A—C19—H19B	109.5
O2—C9—N3	124.39 (12)	S1—C19—H19C	109.5
N2—C9—N3	110.99 (11)	H19A—C19—H19C	109.5
N4—C10—C12	115.80 (11)	H19B—C19—H19C	109.5

C7—N1—N2—C9	−179.85 (12)	N1—N2—C9—N3	179.57 (11)
C9—N3—N4—C10	−178.29 (11)	N4—N3—C9—O2	0.0 (2)
O1—C1—C2—C3	−179.82 (13)	N4—N3—C9—N2	−179.96 (11)
C6—C1—C2—C3	0.3 (2)	N3—N4—C10—C12	179.97 (11)
C1—C2—C3—C4	−0.4 (2)	N3—N4—C10—C11	0.31 (19)
C2—C3—C4—C5	−0.1 (2)	N4—C10—C12—C17	−175.46 (12)
C3—C4—C5—C6	0.6 (2)	C11—C10—C12—C17	4.20 (19)
C4—C5—C6—C1	−0.6 (2)	N4—C10—C12—C13	3.63 (18)
C4—C5—C6—C7	−179.69 (13)	C11—C10—C12—C13	−176.71 (12)
O1—C1—C6—C5	−179.69 (13)	C17—C12—C13—O3	176.40 (12)
C2—C1—C6—C5	0.1 (2)	C10—C12—C13—O3	−2.72 (19)
O1—C1—C6—C7	−0.6 (2)	C17—C12—C13—C14	−2.83 (18)
C2—C1—C6—C7	179.18 (12)	C10—C12—C13—C14	178.05 (12)
N2—N1—C7—C6	−178.82 (11)	O3—C13—C14—C15	−176.70 (12)
N2—N1—C7—C8	−0.32 (19)	C12—C13—C14—C15	2.6 (2)
C5—C6—C7—N1	−171.33 (12)	C13—C14—C15—C16	−0.3 (2)
C1—C6—C7—N1	9.66 (18)	C14—C15—C16—C17	−1.7 (2)
C5—C6—C7—C8	10.15 (19)	C15—C16—C17—C12	1.3 (2)
C1—C6—C7—C8	−168.86 (12)	C13—C12—C17—C16	0.9 (2)
N1—N2—C9—O2	−0.4 (2)	C10—C12—C17—C16	−179.98 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.84	1.79	2.5682 (15)	153
O3—H3o···N4	0.84	1.78	2.5450 (15)	150
N2—H2n···O4ⁱ	0.88	1.94	2.7674 (15)	156
N3—H3n···O4ⁱ	0.88	1.97	2.7907 (15)	154
C19—H19b···O2ⁱⁱ	0.98	2.49	3.2167 (17)	131
C8—H8A···Cg2ⁱⁱⁱ	0.98	2.83	3.5018 (16)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.84	1.79	2.5682 (15)	153
O3—H3o⋯N4	0.84	1.78	2.5450 (15)	150
N2—H2n⋯O4ⁱ	0.88	1.94	2.7674 (15)	156
N3—H3n⋯O4ⁱ	0.88	1.97	2.7907 (15)	154
C19—H19b⋯O2ⁱⁱ	0.98	2.49	3.2167 (17)	131
C8—H8A⋯Cg2ⁱⁱⁱ	0.98	2.83	3.5018 (16)	127

Symmetry codes: (i) ; (ii) ; (iii) . Cg2 is the centroid of the C12–C17 ring.

1 in total

1. A short history of SHELX.

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

1 in total

6 in total

1. 1,5-Bis-[1-(2-hy-droxy-phen-yl)ethyl-idene]carbonohydrazide dimethyl-formamide monosolvate.

Authors: Lingyun Du; Wenkang Zhang
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-09-30

2. 1,5-Bis[(E)-1-(2-hydroxyphenyl)ethyl-idene]thiocarbonohydrazide mono-hydrate.

Authors: Md Abu Affan; Dayang N A Chee; Fasihuddin B Ahmad; Edward R T Tiekink
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-02-06

3. Intramolecular chalcogen-tin interactions in [(o-MeEC6H4)CH2]2SnPh(2-n)Cl(n) (E = S, O, CH2; n = 0, 1, 2) and intermolecular chlorine-tin interactions in the meta- and para-methoxy isomers.

Authors: Diana Gabriela Vargas-Pineda; Tanya Guardado; Francisco Cervantes-Lee; Alejandro J Metta-Magana; Keith H Pannell
Journal: Inorg Chem Date: 2010-02-01 Impact factor: 5.165