Literature DB >> 21522331

4,4'-Bis[(E)-(2,3-diiodo-prop-2-en-1-yl)-oxy]biphen-yl.

Kiramat Shah, M Raza Shah, Seik Weng Ng.

Abstract

Iodine adds across both triple bonds of 4,4'-bis-(prop-2-yn--yl-oxy)biphenyl, yielding the 4,4'-bis-(2,3-diiodo-all-yloxy)biphenyl title compound, C(18)H(14)I(4)O(2); the 2,3-diiodo-ally-oxy substituents have the I atoms in an E configuration. In the biphenyl portion of the mol-ecule, the aromatic rings are inclined by 37.8 (2)°.

Entities: Chemical Disease Gene

Year: 2011 PMID： 21522331 PMCID： PMC3052146 DOI： 10.1107/S1600536811003874

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

Related literature

For the structure of 4,4′-bis(prop-2-ynyloxy)biphenyl, see: Zhang et al. (2008 ▶).

Experimental

Crystal data

C18H14I4O2 M = 769.89 Triclinic, a = 10.0470 (4) Å b = 10.2267 (4) Å c = 11.3581 (4) Å α = 105.760 (4)° β = 101.433 (3)° γ = 108.211 (4)° V = 1014.45 (7) Å3 Z = 2 Mo Kα radiation μ = 6.15 mm−1 T = 100 K 0.20 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.467, T max = 1.000 8121 measured reflections 4502 independent reflections 4118 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.030 wR(F 2) = 0.079 S = 1.04 4502 reflections 217 parameters H-atom parameters constrained Δρmax = 3.38 e Å−3 Δρmin = −1.69 e Å−3 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 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003874/jh2264sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003874/jh2264Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₈H₁₄I₄O₂	Z = 2
M_r = 769.89	F(000) = 700
Triclinic, P1	D_x = 2.520 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0470 (4) Å	Cell parameters from 5987 reflections
b = 10.2267 (4) Å	θ = 2.4–29.2°
c = 11.3581 (4) Å	µ = 6.15 mm⁻¹
α = 105.760 (4)°	T = 100 K
β = 101.433 (3)°	Prism, colorless
γ = 108.211 (4)°	0.20 × 0.10 × 0.05 mm
V = 1014.45 (7) Å³

Agilent SuperNova Dual diffractometer with an Atlas detector	4502 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4118 reflections with I > 2σ(I)
Mirror	R_int = 0.026
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.4°
ω scans	h = −12→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −13→13
T_min = 0.467, T_max = 1.000	l = −9→14
8121 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0391P)² + 2.8781P] where P = (F_o² + 2F_c²)/3
4502 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 3.38 e Å⁻³
0 restraints	Δρ_min = −1.69 e Å⁻³

	x	y	z	U_iso*/U_eq
I1	0.52321 (3)	0.89339 (3)	0.77411 (3)	0.02006 (8)
I2	0.05784 (3)	0.47289 (3)	0.70014 (3)	0.02903 (10)
I3	0.69630 (3)	−0.38925 (3)	0.56256 (3)	0.02370 (9)
I4	1.15769 (3)	−0.03766 (3)	0.91544 (3)	0.02524 (9)
O1	0.5470 (4)	0.7096 (3)	0.9645 (3)	0.0202 (6)
O2	0.8521 (4)	−0.0703 (3)	0.5344 (3)	0.0200 (6)
C1	0.2354 (5)	0.6460 (5)	0.6979 (5)	0.0207 (9)
H1	0.2259	0.6735	0.6242	0.025*
C2	0.3610 (5)	0.7193 (5)	0.7945 (4)	0.0181 (9)
C3	0.3993 (5)	0.7013 (5)	0.9214 (4)	0.0194 (9)
H3A	0.3862	0.7788	0.9867	0.023*
H3B	0.3297	0.6046	0.9150	0.023*
C4	0.5783 (5)	0.5922 (5)	0.9042 (4)	0.0177 (9)
C5	0.7224 (5)	0.6043 (5)	0.9543 (4)	0.0182 (9)
H5	0.7893	0.6881	1.0270	0.022*
C6	0.7679 (5)	0.4940 (5)	0.8981 (4)	0.0184 (9)
H6	0.8666	0.5044	0.9316	0.022*
C7	0.6700 (5)	0.3677 (5)	0.7927 (4)	0.0167 (8)
C8	0.5257 (5)	0.3563 (5)	0.7479 (4)	0.0193 (9)
H8	0.4568	0.2704	0.6782	0.023*
C9	0.4797 (5)	0.4667 (5)	0.8023 (4)	0.0194 (9)
H9	0.3806	0.4559	0.7696	0.023*
C10	0.7198 (5)	0.2529 (5)	0.7296 (4)	0.0160 (8)
C11	0.6679 (5)	0.1820 (5)	0.5947 (4)	0.0189 (9)
H11	0.5995	0.2077	0.5448	0.023*
C12	0.7143 (5)	0.0756 (5)	0.5334 (4)	0.0191 (9)
H12	0.6784	0.0294	0.4424	0.023*
C13	0.8144 (5)	0.0367 (4)	0.6066 (4)	0.0163 (8)
C14	0.8670 (5)	0.1041 (5)	0.7393 (4)	0.0181 (9)
H14	0.9346	0.0775	0.7891	0.022*
C15	0.8192 (5)	0.2116 (5)	0.7992 (4)	0.0172 (8)
H15	0.8558	0.2579	0.8902	0.021*
C16	0.9582 (5)	−0.1128 (5)	0.6013 (4)	0.0192 (9)
H16A	1.0423	−0.0230	0.6631	0.023*
H16B	0.9961	−0.1666	0.5386	0.023*
C17	0.8964 (5)	−0.2085 (5)	0.6726 (4)	0.0172 (8)
C18	0.9551 (5)	−0.1992 (5)	0.7908 (4)	0.0201 (9)
H18	0.9018	−0.2705	0.8211	0.024*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01788 (15)	0.02009 (15)	0.01828 (15)	0.00200 (11)	0.00372 (11)	0.00864 (12)
I2	0.01896 (17)	0.01891 (16)	0.0441 (2)	0.00325 (12)	0.01327 (14)	0.00592 (14)
I3	0.01724 (16)	0.02002 (16)	0.02533 (16)	0.00179 (12)	0.00369 (12)	0.00383 (13)
I4	0.02077 (16)	0.02426 (17)	0.02344 (16)	0.01197 (13)	−0.00226 (12)	0.00046 (13)
O1	0.0246 (17)	0.0183 (15)	0.0189 (15)	0.0112 (13)	0.0053 (13)	0.0061 (13)
O2	0.0263 (17)	0.0199 (16)	0.0201 (15)	0.0149 (13)	0.0081 (13)	0.0091 (13)
C1	0.014 (2)	0.014 (2)	0.031 (2)	0.0025 (17)	0.0072 (18)	0.0052 (19)
C2	0.016 (2)	0.014 (2)	0.025 (2)	0.0055 (16)	0.0100 (18)	0.0060 (18)
C3	0.025 (2)	0.019 (2)	0.020 (2)	0.0116 (18)	0.0126 (18)	0.0093 (18)
C4	0.024 (2)	0.016 (2)	0.019 (2)	0.0100 (17)	0.0108 (18)	0.0092 (17)
C5	0.022 (2)	0.014 (2)	0.018 (2)	0.0051 (17)	0.0054 (17)	0.0076 (17)
C6	0.016 (2)	0.020 (2)	0.020 (2)	0.0060 (17)	0.0037 (17)	0.0105 (18)
C7	0.020 (2)	0.016 (2)	0.018 (2)	0.0073 (17)	0.0059 (17)	0.0100 (17)
C8	0.019 (2)	0.018 (2)	0.021 (2)	0.0078 (18)	0.0058 (17)	0.0058 (18)
C9	0.018 (2)	0.021 (2)	0.022 (2)	0.0095 (18)	0.0062 (18)	0.0090 (19)
C10	0.016 (2)	0.014 (2)	0.018 (2)	0.0027 (16)	0.0060 (16)	0.0086 (17)
C11	0.017 (2)	0.020 (2)	0.021 (2)	0.0087 (18)	0.0041 (17)	0.0096 (18)
C12	0.021 (2)	0.019 (2)	0.017 (2)	0.0074 (18)	0.0055 (17)	0.0070 (18)
C13	0.017 (2)	0.0123 (19)	0.022 (2)	0.0045 (16)	0.0078 (17)	0.0088 (17)
C14	0.019 (2)	0.016 (2)	0.021 (2)	0.0067 (17)	0.0061 (17)	0.0113 (18)
C15	0.016 (2)	0.014 (2)	0.018 (2)	0.0037 (16)	0.0021 (16)	0.0054 (17)
C16	0.020 (2)	0.019 (2)	0.025 (2)	0.0107 (18)	0.0099 (18)	0.0131 (19)
C17	0.014 (2)	0.014 (2)	0.021 (2)	0.0053 (16)	0.0051 (17)	0.0041 (17)
C18	0.019 (2)	0.017 (2)	0.023 (2)	0.0063 (17)	0.0042 (18)	0.0077 (18)

I1—C2	2.107 (4)	C7—C10	1.482 (6)
I2—C1	2.094 (4)	C8—C9	1.389 (6)
I3—C17	2.109 (4)	C8—H8	0.9500
I4—C18	2.089 (5)	C9—H9	0.9500
O1—C4	1.372 (5)	C10—C15	1.390 (6)
O1—C3	1.435 (6)	C10—C11	1.410 (6)
O2—C13	1.381 (5)	C11—C12	1.386 (6)
O2—C16	1.432 (5)	C11—H11	0.9500
C1—C2	1.331 (7)	C12—C13	1.400 (6)
C1—H1	0.9500	C12—H12	0.9500
C2—C3	1.493 (6)	C13—C14	1.386 (6)
C3—H3A	0.9900	C14—C15	1.398 (6)
C3—H3B	0.9900	C14—H14	0.9500
C4—C9	1.383 (6)	C15—H15	0.9500
C4—C5	1.399 (6)	C16—C17	1.500 (6)
C5—C6	1.392 (6)	C16—H16A	0.9900
C5—H5	0.9500	C16—H16B	0.9900
C6—C7	1.403 (6)	C17—C18	1.319 (6)
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.395 (6)

C4—O1—C3	118.0 (3)	C8—C9—H9	120.1
C13—O2—C16	117.6 (3)	C15—C10—C11	117.5 (4)
C2—C1—I2	123.3 (4)	C15—C10—C7	122.1 (4)
C2—C1—H1	118.3	C11—C10—C7	120.4 (4)
I2—C1—H1	118.3	C12—C11—C10	121.5 (4)
C1—C2—C3	128.2 (4)	C12—C11—H11	119.3
C1—C2—I1	117.0 (3)	C10—C11—H11	119.3
C3—C2—I1	114.7 (3)	C11—C12—C13	119.5 (4)
O1—C3—C2	113.8 (4)	C11—C12—H12	120.2
O1—C3—H3A	108.8	C13—C12—H12	120.2
C2—C3—H3A	108.8	C14—C13—O2	125.7 (4)
O1—C3—H3B	108.8	C14—C13—C12	120.3 (4)
C2—C3—H3B	108.8	O2—C13—C12	114.0 (4)
H3A—C3—H3B	107.7	C13—C14—C15	119.2 (4)
O1—C4—C9	125.3 (4)	C13—C14—H14	120.4
O1—C4—C5	115.2 (4)	C15—C14—H14	120.4
C9—C4—C5	119.5 (4)	C10—C15—C14	122.0 (4)
C6—C5—C4	120.2 (4)	C10—C15—H15	119.0
C6—C5—H5	119.9	C14—C15—H15	119.0
C4—C5—H5	119.9	O2—C16—C17	113.0 (4)
C5—C6—C7	120.9 (4)	O2—C16—H16A	109.0
C5—C6—H6	119.5	C17—C16—H16A	109.0
C7—C6—H6	119.5	O2—C16—H16B	109.0
C8—C7—C6	117.5 (4)	C17—C16—H16B	109.0
C8—C7—C10	121.5 (4)	H16A—C16—H16B	107.8
C6—C7—C10	121.0 (4)	C18—C17—C16	128.5 (4)
C9—C8—C7	122.0 (4)	C18—C17—I3	116.8 (3)
C9—C8—H8	119.0	C16—C17—I3	114.6 (3)
C7—C8—H8	119.0	C17—C18—I4	124.2 (4)
C4—C9—C8	119.8 (4)	C17—C18—H18	117.9
C4—C9—H9	120.1	I4—C18—H18	117.9

I2—C1—C2—C3	−3.1 (7)	C8—C7—C10—C11	37.3 (6)
I2—C1—C2—I1	−178.41 (19)	C6—C7—C10—C11	−141.2 (4)
C4—O1—C3—C2	−73.4 (5)	C15—C10—C11—C12	−0.3 (7)
C1—C2—C3—O1	139.5 (5)	C7—C10—C11—C12	179.2 (4)
I1—C2—C3—O1	−45.1 (4)	C10—C11—C12—C13	0.3 (7)
C3—O1—C4—C9	1.6 (6)	C16—O2—C13—C14	−2.1 (6)
C3—O1—C4—C5	−177.3 (4)	C16—O2—C13—C12	177.8 (4)
O1—C4—C5—C6	−177.9 (4)	C11—C12—C13—C14	−0.1 (7)
C9—C4—C5—C6	3.1 (6)	C11—C12—C13—O2	−179.9 (4)
C4—C5—C6—C7	−1.5 (7)	O2—C13—C14—C15	179.6 (4)
C5—C6—C7—C8	−0.9 (6)	C12—C13—C14—C15	−0.2 (6)
C5—C6—C7—C10	177.6 (4)	C11—C10—C15—C14	0.0 (6)
C6—C7—C8—C9	1.8 (7)	C7—C10—C15—C14	−179.5 (4)
C10—C7—C8—C9	−176.8 (4)	C13—C14—C15—C10	0.3 (7)
O1—C4—C9—C8	178.9 (4)	C13—O2—C16—C17	74.9 (5)
C5—C4—C9—C8	−2.3 (7)	O2—C16—C17—C18	−135.0 (5)
C7—C8—C9—C4	−0.2 (7)	O2—C16—C17—I3	49.6 (4)
C8—C7—C10—C15	−143.3 (4)	C16—C17—C18—I4	1.3 (7)
C6—C7—C10—C15	38.2 (6)	I3—C17—C18—I4	176.6 (2)

2 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. 4,4'-Bis(prop-2-yn-yloxy)biphen-yl.

Authors: Wu Zhang; Li Yao; Ruo-Jie Tao
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2007-12-18

2 in total

1 in total

1. Methyl 2,2-diphenyl-2-(prop-2-yn-1-yl-oxy)acetate.

Authors: H P Sumathi; Ulrich Flörke; H S Yathirajan; A S Dayananda; A R Ramesha
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-02-29

1 in total