Literature DB >> 22064780

N'-[(E)-2-Hy-droxy-3,5-diiodo-benzyl-idene]cyclo-hexa-ne-1-carbohydrazide.

A Thirugnanasundar, J Suresh, C Meenakshi, G Chakkaravarthi, G Rajagopal.

Abstract

In the title compound, C(14)H(10)I(2)N(2)O(2), the two aromatic rings are inclined at a dihedral angle of 16.72 (33)°. The mol-ecular structure is stabilized by an intra-molecular O-H⋯N hydrogen bond. In the crystal, inter-molecular N-H⋯O inter-actions link the mol-ecules into chains running along the c axis. C-H⋯O inter-actions also occur. The crystal used for the structure determination was a non-merohedral twin with a domain ratio of 0.972 (2):0.028 (2).

Entities: Chemical Disease Gene

Year: 2011 PMID： 22064780 PMCID： PMC3201245 DOI： 10.1107/S1600536811036488

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

Related literature

For the biological activity of Schiff base derivatives, see: Daier et al. (2004 ▶); Golcu et al. (2005 ▶); Liu & Yang (2010 ▶); Zgierski & Grabowska (2000 ▶). For related structures, see: Manvizhi et al. (2011 ▶); Thirugnanasundar et al. (2011 ▶).

Experimental

Crystal data

C14H10I2N2O2 M = 492.04 Monoclinic, a = 17.7495 (13) Å b = 9.4273 (6) Å c = 9.4684 (7) Å β = 103.052 (3)° V = 1543.42 (19) Å3 Z = 4 Mo Kα radiation μ = 4.08 mm−1 T = 295 K 0.20 × 0.10 × 0.10 mm

Data collection

Bruker Kappa APEXII diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.496, T max = 0.686 13146 measured reflections 2708 independent reflections 2349 reflections with I > 2σ(I) R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.058 wR(F 2) = 0.172 S = 1.11 2708 reflections 182 parameters H-atom parameters constrained Δρmax = 1.48 e Å−3 Δρmin = −1.52 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036488/bt5637sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036488/bt5637Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811036488/bt5637Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₄H₁₀I₂N₂O₂	F(000) = 920
M_r = 492.04	D_x = 2.118 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 13146 reflections
a = 17.7495 (13) Å	θ = 2.2–25.0°
b = 9.4273 (6) Å	µ = 4.08 mm⁻¹
c = 9.4684 (7) Å	T = 295 K
β = 103.052 (3)°	Block, yellow
V = 1543.42 (19) Å³	0.20 × 0.10 × 0.10 mm
Z = 4

Bruker Kappa APEXII diffractometer	2708 independent reflections
Radiation source: fine-focus sealed tube	2349 reflections with I > 2σ(I)
graphite	R_int = 0.029
ω and φ scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→21
T_min = 0.496, T_max = 0.686	k = −11→8
13146 measured reflections	l = −11→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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.172	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0412P)² + 42.3729P] where P = (F_o² + 2F_c²)/3
2708 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 1.48 e Å⁻³
0 restraints	Δρ_min = −1.52 e Å⁻³

	x	y	z	U_iso*/U_eq
I1	0.89740 (5)	0.16968 (10)	0.83785 (10)	0.0458 (3)
I2	0.91863 (7)	−0.18253 (14)	1.36905 (13)	0.0777 (5)
O1	0.5247 (5)	0.3352 (11)	0.8089 (10)	0.052 (3)
O2	0.7346 (5)	0.2255 (10)	0.9018 (10)	0.044 (2)
H2A	0.6895	0.2404	0.9145	0.065*
N1	0.5428 (6)	0.2182 (13)	1.0250 (11)	0.043 (3)
H1	0.5244	0.1906	1.0969	0.052*
N2	0.6169 (6)	0.1863 (12)	1.0158 (11)	0.040 (3)
C1	0.4189 (7)	0.3296 (14)	0.9272 (12)	0.036 (3)
C2	0.3821 (7)	0.4436 (15)	0.8509 (13)	0.043 (3)
H2	0.4075	0.4988	0.7950	0.052*
C3	0.3079 (9)	0.4755 (18)	0.8577 (16)	0.057 (4)
H3	0.2836	0.5541	0.8082	0.068*
C4	0.2694 (8)	0.3939 (16)	0.9356 (15)	0.047 (3)
H4	0.2185	0.4156	0.9369	0.057*
C5	0.3052 (7)	0.2777 (15)	1.0138 (13)	0.041 (3)
H5	0.2790	0.2217	1.0678	0.049*
C6	0.3807 (7)	0.2479 (15)	1.0092 (14)	0.041 (3)
H6	0.4060	0.1719	1.0621	0.049*
C7	0.4996 (7)	0.2964 (14)	0.9137 (11)	0.035 (3)
C8	0.6579 (7)	0.1120 (14)	1.1159 (12)	0.036 (3)
H8	0.6375	0.0800	1.1924	0.043*
C9	0.7375 (7)	0.0770 (13)	1.1107 (13)	0.034 (3)
C10	0.7797 (7)	−0.0131 (15)	1.2142 (14)	0.042 (3)
H10	0.7576	−0.0486	1.2872	0.051*
C11	0.8534 (8)	−0.0503 (15)	1.2102 (14)	0.043 (3)
C12	0.8881 (7)	0.0029 (13)	1.1027 (14)	0.040 (3)
H12	0.9385	−0.0225	1.1010	0.048*
C13	0.8471 (7)	0.0932 (13)	0.9997 (13)	0.034 (3)
C14	0.7710 (6)	0.1333 (13)	1.0022 (12)	0.031 (2)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0346 (4)	0.0620 (6)	0.0442 (5)	0.0048 (4)	0.0159 (4)	0.0154 (4)
I2	0.0733 (8)	0.0933 (9)	0.0714 (8)	0.0406 (7)	0.0266 (6)	0.0484 (7)
O1	0.041 (5)	0.074 (7)	0.047 (6)	0.002 (5)	0.021 (4)	0.010 (5)
O2	0.034 (4)	0.048 (5)	0.051 (5)	0.007 (4)	0.015 (4)	0.015 (4)
N1	0.032 (5)	0.064 (7)	0.036 (6)	0.015 (5)	0.015 (4)	0.005 (5)
N2	0.024 (5)	0.058 (7)	0.042 (6)	0.002 (5)	0.017 (4)	−0.006 (5)
C1	0.026 (6)	0.053 (8)	0.025 (6)	0.003 (5)	−0.001 (5)	−0.006 (5)
C2	0.041 (7)	0.054 (8)	0.034 (7)	0.006 (6)	0.006 (6)	0.000 (6)
C3	0.052 (9)	0.066 (10)	0.051 (8)	0.018 (8)	0.010 (7)	0.002 (8)
C4	0.036 (7)	0.055 (9)	0.054 (8)	0.007 (6)	0.016 (6)	−0.002 (7)
C5	0.035 (6)	0.059 (8)	0.033 (6)	0.003 (6)	0.016 (5)	0.003 (6)
C6	0.034 (6)	0.046 (8)	0.046 (7)	0.008 (6)	0.013 (6)	0.010 (6)
C7	0.031 (6)	0.057 (8)	0.017 (5)	0.001 (5)	0.007 (4)	0.001 (5)
C8	0.034 (6)	0.052 (8)	0.023 (6)	0.005 (6)	0.011 (5)	−0.005 (5)
C9	0.034 (6)	0.039 (7)	0.031 (6)	0.003 (5)	0.010 (5)	−0.002 (5)
C10	0.042 (7)	0.053 (8)	0.036 (7)	0.007 (6)	0.016 (6)	0.006 (6)
C11	0.046 (7)	0.048 (8)	0.034 (6)	0.007 (6)	0.008 (6)	0.006 (6)
C12	0.042 (7)	0.037 (7)	0.044 (7)	0.011 (6)	0.016 (6)	0.004 (5)
C13	0.033 (6)	0.037 (7)	0.032 (6)	0.003 (5)	0.008 (5)	−0.002 (5)
C14	0.031 (6)	0.033 (6)	0.028 (6)	0.006 (5)	0.006 (5)	−0.003 (5)

I1—C13	2.070 (12)	C4—C5	1.393 (19)
I2—C11	2.090 (13)	C4—H4	0.9300
O1—C7	1.231 (14)	C5—C6	1.379 (17)
O2—C14	1.342 (14)	C5—H5	0.9300
O2—H2A	0.8480	C6—H6	0.9300
N1—C7	1.370 (15)	C8—C9	1.463 (16)
N1—N2	1.370 (13)	C8—H8	0.9300
N1—H1	0.8600	C9—C10	1.382 (17)
N2—C8	1.268 (16)	C9—C14	1.402 (16)
C1—C2	1.375 (18)	C10—C11	1.363 (18)
C1—C6	1.376 (18)	C10—H10	0.9300
C1—C7	1.500 (16)	C11—C12	1.397 (18)
C2—C3	1.366 (19)	C12—C13	1.373 (17)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.35 (2)	C13—C14	1.409 (16)
C3—H3	0.9300

C14—O2—H2A	108.9	O1—C7—C1	122.2 (11)
C7—N1—N2	116.6 (10)	N1—C7—C1	115.2 (10)
C7—N1—H1	121.7	N2—C8—C9	119.7 (11)
N2—N1—H1	121.7	N2—C8—H8	120.1
C8—N2—N1	118.1 (10)	C9—C8—H8	120.1
C2—C1—C6	119.8 (11)	C10—C9—C14	120.1 (11)
C2—C1—C7	117.9 (12)	C10—C9—C8	119.2 (11)
C6—C1—C7	122.2 (11)	C14—C9—C8	120.8 (11)
C3—C2—C1	119.8 (14)	C11—C10—C9	120.5 (12)
C3—C2—H2	120.1	C11—C10—H10	119.7
C1—C2—H2	120.1	C9—C10—H10	119.7
C4—C3—C2	120.7 (14)	C10—C11—C12	120.8 (12)
C4—C3—H3	119.6	C10—C11—I2	120.9 (10)
C2—C3—H3	119.6	C12—C11—I2	118.3 (9)
C3—C4—C5	120.7 (13)	C13—C12—C11	119.4 (11)
C3—C4—H4	119.6	C13—C12—H12	120.3
C5—C4—H4	119.6	C11—C12—H12	120.3
C6—C5—C4	118.3 (12)	C12—C13—C14	120.7 (11)
C6—C5—H5	120.9	C12—C13—I1	119.6 (9)
C4—C5—H5	120.9	C14—C13—I1	119.7 (9)
C1—C6—C5	120.7 (12)	O2—C14—C9	123.3 (10)
C1—C6—H6	119.7	O2—C14—C13	118.1 (10)
C5—C6—H6	119.7	C9—C14—C13	118.5 (11)
O1—C7—N1	122.6 (11)

C7—N1—N2—C8	−178.8 (12)	N2—C8—C9—C14	4.9 (19)
C6—C1—C2—C3	0(2)	C14—C9—C10—C11	−1(2)
C7—C1—C2—C3	178.5 (12)	C8—C9—C10—C11	178.5 (13)
C1—C2—C3—C4	−2(2)	C9—C10—C11—C12	1(2)
C2—C3—C4—C5	2(2)	C9—C10—C11—I2	178.5 (10)
C3—C4—C5—C6	0(2)	C10—C11—C12—C13	0(2)
C2—C1—C6—C5	1(2)	I2—C11—C12—C13	−178.1 (10)
C7—C1—C6—C5	−177.0 (12)	C11—C12—C13—C14	0.5 (19)
C4—C5—C6—C1	−1(2)	C11—C12—C13—I1	−178.9 (10)
N2—N1—C7—O1	1.0 (19)	C10—C9—C14—O2	−177.3 (12)
N2—N1—C7—C1	−179.9 (11)	C8—C9—C14—O2	2.8 (18)
C2—C1—C7—O1	−22.7 (18)	C10—C9—C14—C13	1.5 (18)
C6—C1—C7—O1	155.4 (13)	C8—C9—C14—C13	−178.4 (11)
C2—C1—C7—N1	158.2 (12)	C12—C13—C14—O2	177.8 (11)
C6—C1—C7—N1	−23.7 (18)	I1—C13—C14—O2	−2.8 (15)
N1—N2—C8—C9	−179.4 (11)	C12—C13—C14—C9	−1.1 (18)
N2—C8—C9—C10	−175.0 (13)	I1—C13—C14—C9	178.3 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N2	0.85	1.84	2.586 (13)	145
N1—H1···O1ⁱ	0.86	2.02	2.824 (14)	155
C3—H3···O2ⁱⁱ	0.93	2.53	3.365 (19)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N2	0.85	1.84	2.586 (13)	145
N1—H1⋯O1ⁱ	0.86	2.02	2.824 (14)	155
C3—H3⋯O2ⁱⁱ	0.93	2.53	3.365 (19)	150

Symmetry codes: (i) ; (ii) .

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