2,2′-{(1E,1′E)-[Ethane-1,2-diylbis(aza­nylyl­idene)]bis­(methanylyl­idene)}bis­(4-iodo­phenol)

Blackwelder, L.A.; Kelley, A.R.; Balaich, G.J.; Jefferies, L.R.

doi:10.1107/S2414314622008951

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 7| Part 9| September 2022| x220895

https://doi.org/10.1107/S2414314622008951

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2,2′-{(1E,1′E)-[Ethane-1,2-diylbis(azanylylidene)]bis(methanylylidene)}bis(4-iodophenol)

Lauren A. Blackwelder,^a Andrea R. Kelley,^a Gary J. Balaich ^a and Latisha R. Jefferies ^a ^*

^aDepartment of Chemistry, US Air Force Academy, CO, 80840, USA
^*Correspondence e-mail: latisha.jefferies@afacademy.af.edu

Edited by J. F. Gallagher, Dublin City University, Ireland (Received 29 June 2022; accepted 6 September 2022; online 13 September 2022)

The title compound, C₂₀H₁₄I₂N₂O₂, a diiodo-Schiff base, crystallizes in space group Pbca with one molecule per asymmetric unit. The molecular structure reveals two intramolecular O—H⋯N hydrogen bonds that give the molecule a twisted structure with non-coplanar rings. In the crystal structure, the molecular packing is stabilized by π–π stacking, hydrogen- and halogen-bonding (C—H⋯I; O⋯I) interactions.

Keywords: crystal structure; Schiff base; hydrogen bonding; π–π stacking.

CCDC reference: 2205660

Structure description

2,2′-{(1E,1′E)-[Ethane-1,2-diylbis(azanylylidene)]bis(methanylylidene)}bis(4-iodophenol) (I) (C₂₀H₁₄I₂N₂O₂, Fig. 1) is a salen-type ligand under investigation in our laboratory for possible antimicrobial effects (Ceramella et al., 2022 ) and the ability to bind to lanthanide metals, which could have other important medicinal properties (Kaczmarek et al., 2018 ). As a result of the wide range of medical applications for such compounds, and in a continuation of our work in this area (Reimann et al., 2019 ), the title compound (I) was prepared and its crystal structure is reported here.

Figure 1
Molecular structure of (I) depicting the two intramolecular hydrogen bonds (O1—H1⋯N1 and O2—H2⋯N2). Displacement ellipsoids are shown at the 50% probability level

Each molecule of (I) consists of a central ring (C8–C13) with ortho imine nitrogen atoms (N1 and N2) covalently bound through the imine C atoms, C7 and C14 respectively, to I1—Ar(O1—H1) and I2—Ar(O2—H2) rings (Fig. 1). Two intramolecular hydrogen bonds (Table 1), O1—H1⋯N1 [1.842 (15) Å, 152 (3)°] and O2—H2⋯N2 [1.806 (15) Å, 153 (3)°], result in an overall non-planar molecule with the I—Ar(OH) ring planes twisted with respect to the central ring (C8–13) plane [24.97 (7)° versus I1—Ar(O1—H1), and 39.37 (5)° versus I2—Ar(O2—H2)] (Fig. 1). The intramolecular hydrogen bonds of (I) show similarity to those of the dichlorinated Schiff base 3,5-dichloro-N-[2-(methylthio)phenyl]salicylaldimine (Hamaker et al., 2010 ). Halogen bonding (I1⋯O2) and slipped π–π stacking interactions stabilize the packing pattern. Along the a-axis direction, adjacent molecules related by 2₁ screw-axis symmetry form 2-stacks/molecule of non-coplanar and alternating central ring (C8–C13) to I2—Ar(O2—H2) ring interactions (Fig. 2). This results in alternating longer [3.821 (13) Å] and shorter [3.734 (13) Å] central ring (C8–C13) centroid to I2—Ar(O2—H2) ring centroid distances with the corresponding alternating centroids slipped by 1.583 (4) and 1.548 (3) Å with respect to each other (Fig. 2). The additional hydrogen bonding provides three shorter and one longer C—H⋯I type interactions in which I2 has a larger displacement ellipsoid than I1 [C18—H18⋯I1 = 3.16 Å (159°), C5—H5⋯I2 = 3.17 Å (156°), C7—H7⋯I2 = 3.23 Å (152°), and C2—H2⋯I2 3.32 Å (131°)]. The two C—I bond lengths of (I) are similar to the C—I bond of 2,3,5,6-tetrafluoro-1,4-diiodobenzene (Tan & Tiekink, 2019 ). Along the b-axis direction, adjacent molecules appear to be arranged in a H (head, central C8–C13 ring) to T [tail, I1—Ar(O1—H1) and I2—Ar(O2—H2) rings] repeating pattern with the I1 and I2 atoms of the I1—Ar(O1—H1) and I2—Ar(O2—H2) rings interdigitated along the c-axis direction (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯I2ⁱ	0.95	3.32	4.009 (2)	131
C5—H5⋯I2ⁱⁱ	0.95	3.17	4.061 (2)	156
C7—H7⋯I2ⁱⁱ	0.95	3.23	4.094 (2)	152
C18—H18⋯I1ⁱⁱⁱ	0.95	3.16	4.066 (2)	159
O1—H1⋯N1	0.84 (1)	1.84 (2)	2.609 (3)	152 (3)
O2—H2⋯N2	0.84 (1)	1.81 (2)	2.580 (3)	153 (3)
Symmetry codes: (i) ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y, z-{\script{1\over 2}}]$ .

Figure 2
Diagram of the basic packing motif along the a-axis direction depicting the slipped ring π–π interactions.

Figure 3
Molecular packing view of (I) along the a-axis direction. Displacement ellipsoids are shown at the 50% probability level.

Synthesis and crystallization

To a solution of 2-hydroxy-5-iodobenzaldehyde (4.60 g, 18.5 mmol) in ethanol (200 ml) was added an ethanol (10 ml) solution of o-phenylenediamine (1.00 g, 9.20 mmol), and the reaction mixture brought to reflux with vigorous stirring for 2 h. Upon cooling, the title compound (I) precipitated as an orange solid, and was filtered, washed with ethanol and dried under vacuum. Crystals of (I) suitable for single-crystal X-ray diffraction were grown from acetone layered with hexane. Yield: 4.37 g (83%), m.p. 212–214°C. ¹H NMR (500 MHz, CDCl₃) δ 8.54 (s, 2H), 7.73–7.54 (m, 4H), 7.37 (q, J = 3.2 Hz, 2H), 7.22 (q, J = 3.2 Hz, 2H), 6.84 (d, J = 9.0 Hz, 2H). [Note: phenolic H atoms (2Hs) undergo rapid exchange thus their NMR signals are broadened into the baseline beyond recognition as reported (Charisiadis et al., 2014 ).] ¹³C NMR (500 MHz, CDCl₃) δ 162.30, 161.11, 142.25, 141.81, 140.46, 128.32, 121.46, 120.15, 119.63, 79.69. MALDI–TOF MS: monoisotopic m/z calculated for [M + H]⁺: 568.9; observed: 568.8.

Refinement

Crystal data, data collection and structure refinement details of (I) are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₀H₁₄I₂N₂O₂
M_r	568.13
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	112
a, b, c (Å)	7.4776 (1), 19.1040 (2), 26.0919 (3)
V (Å³)	3727.28 (8)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	3.39
Crystal size (mm)	0.30 × 0.26 × 0.12

Data collection
Diffractometer	XtaLAB Synergy, Single source at offset/far, HyPix3000
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.300, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	34066, 4062, 3774
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.044, 1.09
No. of reflections	4062
No. of parameters	242
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.92
Computer programs: CrysAlis PRO (Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT2014/5 (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2205660

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314622008951/gg4010sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314622008951/gg4010Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2019); cell refinement: CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(I) top

Crystal data top

C₂₀H₁₄I₂N₂O₂	D_x = 2.025 Mg m⁻³
M_r = 568.13	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 25879 reflections
a = 7.4776 (1) Å	θ = 1.5–27.4°
b = 19.1040 (2) Å	µ = 3.39 mm⁻¹
c = 26.0919 (3) Å	T = 112 K
V = 3727.28 (8) Å³	Rect. Prism, orange
Z = 8	0.30 × 0.26 × 0.12 mm
F(000) = 2160

Data collection top

XtaLAB Synergy, Single source at offset/far, HyPix3000 diffractometer	4062 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Mo) X-ray Source	3774 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.033
Detector resolution: 10.0000 pixels mm^-1	θ_max = 27.4°, θ_min = 1.6°
ω scans	h = −9→9
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2019)	k = −23→24
T_min = 0.300, T_max = 1.000	l = −32→32
34066 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.020	w = 1/[σ²(F_o²) + (0.0133P)² + 5.3948P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.044	(Δ/σ)_max = 0.002
S = 1.09	Δρ_max = 0.66 e Å⁻³
4062 reflections	Δρ_min = −0.92 e Å⁻³
242 parameters	Extinction correction: SHELXL-2016/6 (Sheldrick 2015b, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.000120 (17)
Primary atom site location: dual

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.48524 (2)	0.12444 (2)	0.85138 (2)	0.01709 (5)
I2	0.28304 (3)	0.11138 (2)	0.30070 (2)	0.03584 (7)
O1	0.4758 (2)	0.15083 (9)	0.61326 (6)	0.0205 (4)
O2	0.1200 (2)	0.13607 (9)	0.53361 (6)	0.0233 (4)
N1	0.3343 (3)	0.27475 (10)	0.62428 (7)	0.0162 (4)
N2	0.1963 (3)	0.26760 (10)	0.52825 (7)	0.0163 (4)
C1	0.4718 (3)	0.14643 (12)	0.66467 (9)	0.0159 (5)
C2	0.5299 (3)	0.08468 (12)	0.68798 (9)	0.0183 (5)
H2A	0.569184	0.046666	0.667387	0.022*
C3	0.5307 (3)	0.07839 (12)	0.74077 (9)	0.0181 (5)
H3	0.571539	0.036324	0.756275	0.022*
C4	0.4721 (3)	0.13336 (12)	0.77109 (9)	0.0158 (5)
C5	0.4097 (3)	0.19424 (12)	0.74922 (9)	0.0162 (5)
H5	0.367238	0.231184	0.770347	0.019*
C6	0.4087 (3)	0.20174 (12)	0.69545 (8)	0.0154 (5)
C7	0.3358 (3)	0.26551 (12)	0.67317 (8)	0.0167 (5)
H7	0.288625	0.300786	0.694995	0.020*
C8	0.2667 (3)	0.33732 (12)	0.60266 (8)	0.0152 (5)
C9	0.2710 (3)	0.40210 (13)	0.62775 (9)	0.0190 (5)
H9	0.316488	0.405051	0.661683	0.023*
C10	0.2096 (3)	0.46185 (12)	0.60350 (9)	0.0201 (5)
H10	0.212521	0.505533	0.620872	0.024*
C11	0.1437 (3)	0.45812 (12)	0.55393 (9)	0.0199 (5)
H11	0.100415	0.499165	0.537540	0.024*
C12	0.1408 (3)	0.39464 (12)	0.52821 (9)	0.0192 (5)
H12	0.095597	0.392368	0.494231	0.023*
C13	0.2040 (3)	0.33413 (12)	0.55195 (8)	0.0154 (5)
C14	0.2275 (3)	0.26073 (12)	0.47991 (8)	0.0161 (5)
H14	0.260311	0.300477	0.460144	0.019*
C15	0.2129 (3)	0.19260 (12)	0.45542 (8)	0.0156 (5)
C16	0.1605 (3)	0.13285 (12)	0.48342 (9)	0.0165 (5)
C17	0.1499 (3)	0.06804 (12)	0.45880 (9)	0.0180 (5)
H17	0.115967	0.027658	0.477692	0.022*
C18	0.1884 (3)	0.06224 (12)	0.40725 (9)	0.0186 (5)
H18	0.181371	0.018057	0.390663	0.022*
C19	0.2375 (3)	0.12147 (12)	0.37979 (9)	0.0183 (5)
C20	0.2510 (3)	0.18604 (12)	0.40303 (8)	0.0168 (5)
H20	0.285889	0.225866	0.383654	0.020*
H1	0.428 (3)	0.1892 (8)	0.6061 (10)	0.020*
H2	0.139 (3)	0.1776 (7)	0.5419 (9)	0.020*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01938 (8)	0.01833 (8)	0.01356 (8)	−0.00151 (6)	−0.00173 (6)	0.00283 (5)
I2	0.07494 (16)	0.01979 (9)	0.01279 (9)	0.00557 (9)	0.00604 (8)	−0.00114 (6)
O1	0.0249 (9)	0.0219 (9)	0.0145 (8)	0.0034 (7)	0.0003 (7)	−0.0015 (7)
O2	0.0358 (10)	0.0204 (9)	0.0136 (8)	−0.0054 (8)	0.0043 (7)	0.0029 (7)
N1	0.0167 (10)	0.0177 (10)	0.0142 (9)	−0.0021 (8)	−0.0008 (8)	0.0004 (8)
N2	0.0172 (10)	0.0182 (10)	0.0135 (9)	−0.0003 (8)	−0.0012 (8)	−0.0005 (8)
C1	0.0121 (11)	0.0218 (12)	0.0138 (11)	−0.0023 (9)	−0.0012 (9)	−0.0008 (9)
C2	0.0162 (11)	0.0177 (12)	0.0211 (12)	0.0006 (9)	0.0006 (9)	−0.0046 (9)
C3	0.0149 (11)	0.0180 (12)	0.0215 (12)	0.0000 (9)	−0.0022 (9)	0.0022 (10)
C4	0.0161 (11)	0.0187 (11)	0.0127 (11)	−0.0035 (9)	−0.0009 (9)	0.0001 (9)
C5	0.0167 (11)	0.0181 (11)	0.0138 (10)	−0.0004 (10)	−0.0006 (9)	−0.0010 (9)
C6	0.0145 (11)	0.0170 (11)	0.0148 (11)	−0.0020 (9)	−0.0013 (9)	−0.0004 (9)
C7	0.0180 (11)	0.0171 (11)	0.0150 (11)	−0.0018 (9)	−0.0005 (9)	−0.0033 (9)
C8	0.0152 (11)	0.0155 (11)	0.0149 (11)	0.0001 (9)	0.0018 (9)	0.0008 (9)
C9	0.0203 (12)	0.0209 (12)	0.0157 (11)	−0.0029 (10)	0.0003 (9)	−0.0025 (10)
C10	0.0192 (12)	0.0163 (11)	0.0248 (12)	−0.0009 (10)	0.0035 (10)	−0.0042 (10)
C11	0.0195 (12)	0.0161 (11)	0.0241 (12)	0.0030 (10)	0.0025 (10)	0.0041 (10)
C12	0.0205 (12)	0.0206 (12)	0.0165 (11)	0.0016 (10)	−0.0017 (10)	0.0020 (9)
C13	0.0148 (11)	0.0165 (11)	0.0149 (11)	−0.0004 (9)	0.0020 (9)	0.0010 (9)
C14	0.0163 (11)	0.0170 (11)	0.0150 (11)	−0.0010 (9)	−0.0016 (9)	0.0023 (9)
C15	0.0147 (11)	0.0186 (11)	0.0135 (11)	−0.0010 (9)	−0.0017 (9)	0.0006 (9)
C16	0.0165 (11)	0.0193 (12)	0.0136 (11)	−0.0004 (9)	−0.0006 (9)	0.0029 (9)
C17	0.0196 (12)	0.0165 (11)	0.0179 (11)	−0.0027 (10)	−0.0009 (10)	0.0036 (9)
C18	0.0202 (12)	0.0157 (11)	0.0199 (12)	−0.0005 (9)	−0.0027 (10)	−0.0017 (9)
C19	0.0244 (12)	0.0188 (12)	0.0117 (11)	0.0023 (10)	0.0005 (9)	−0.0001 (9)
C20	0.0215 (12)	0.0151 (11)	0.0138 (11)	−0.0014 (9)	0.0009 (9)	0.0015 (9)

Geometric parameters (Å, º) top

I1—C4	2.104 (2)	C8—C9	1.401 (3)
I2—C19	2.100 (2)	C8—C13	1.405 (3)
O1—C1	1.344 (3)	C9—H9	0.9500
O1—H1	0.835 (10)	C9—C10	1.384 (3)
O2—C16	1.345 (3)	C10—H10	0.9500
O2—H2	0.836 (10)	C10—C11	1.386 (3)
N1—C7	1.288 (3)	C11—H11	0.9500
N1—C8	1.415 (3)	C11—C12	1.386 (3)
N2—C13	1.415 (3)	C12—H12	0.9500
N2—C14	1.290 (3)	C12—C13	1.394 (3)
C1—C2	1.397 (3)	C14—H14	0.9500
C1—C6	1.409 (3)	C14—C15	1.454 (3)
C2—H2A	0.9500	C15—C16	1.411 (3)
C2—C3	1.383 (3)	C15—C20	1.402 (3)
C3—H3	0.9500	C16—C17	1.397 (3)
C3—C4	1.386 (3)	C17—H17	0.9500
C4—C5	1.377 (3)	C17—C18	1.380 (3)
C5—H5	0.9500	C18—H18	0.9500
C5—C6	1.410 (3)	C18—C19	1.389 (3)
C6—C7	1.456 (3)	C19—C20	1.378 (3)
C7—H7	0.9500	C20—H20	0.9500

C1—O1—H1	105.6 (18)	C9—C10—C11	120.2 (2)
C16—O2—H2	104.9 (18)	C11—C10—H10	119.9
C7—N1—C8	120.9 (2)	C10—C11—H11	119.9
C14—N2—C13	120.8 (2)	C10—C11—C12	120.1 (2)
O1—C1—C2	118.7 (2)	C12—C11—H11	119.9
O1—C1—C6	122.0 (2)	C11—C12—H12	119.8
C2—C1—C6	119.3 (2)	C11—C12—C13	120.3 (2)
C1—C2—H2A	119.7	C13—C12—H12	119.8
C3—C2—C1	120.6 (2)	C8—C13—N2	117.7 (2)
C3—C2—H2A	119.7	C12—C13—N2	122.5 (2)
C2—C3—H3	120.0	C12—C13—C8	119.7 (2)
C2—C3—C4	120.1 (2)	N2—C14—H14	119.8
C4—C3—H3	120.0	N2—C14—C15	120.5 (2)
C3—C4—I1	119.49 (17)	C15—C14—H14	119.8
C5—C4—I1	119.79 (17)	C16—C15—C14	121.2 (2)
C5—C4—C3	120.7 (2)	C20—C15—C14	119.6 (2)
C4—C5—H5	120.0	C20—C15—C16	119.3 (2)
C4—C5—C6	120.0 (2)	O2—C16—C15	122.0 (2)
C6—C5—H5	120.0	O2—C16—C17	118.4 (2)
C1—C6—C5	119.3 (2)	C17—C16—C15	119.6 (2)
C1—C6—C7	121.7 (2)	C16—C17—H17	119.8
C5—C6—C7	119.0 (2)	C18—C17—C16	120.5 (2)
N1—C7—C6	120.9 (2)	C18—C17—H17	119.8
N1—C7—H7	119.6	C17—C18—H18	120.2
C6—C7—H7	119.6	C17—C18—C19	119.5 (2)
C9—C8—N1	123.5 (2)	C19—C18—H18	120.2
C9—C8—C13	119.1 (2)	C18—C19—I2	118.35 (17)
C13—C8—N1	117.3 (2)	C20—C19—I2	120.16 (17)
C8—C9—H9	119.7	C20—C19—C18	121.5 (2)
C10—C9—C8	120.5 (2)	C15—C20—H20	120.2
C10—C9—H9	119.7	C19—C20—C15	119.6 (2)
C9—C10—H10	119.9	C19—C20—H20	120.2

I1—C4—C5—C6	176.96 (17)	C8—N1—C7—C6	−178.7 (2)
I2—C19—C20—C15	177.30 (17)	C8—C9—C10—C11	−0.3 (4)
O1—C1—C2—C3	178.9 (2)	C9—C8—C13—N2	−178.1 (2)
O1—C1—C6—C5	−179.3 (2)	C9—C8—C13—C12	−2.5 (3)
O1—C1—C6—C7	3.2 (3)	C9—C10—C11—C12	−0.7 (4)
O2—C16—C17—C18	179.4 (2)	C10—C11—C12—C13	0.0 (4)
N1—C8—C9—C10	177.2 (2)	C11—C12—C13—N2	177.0 (2)
N1—C8—C13—N2	6.2 (3)	C11—C12—C13—C8	1.6 (3)
N1—C8—C13—C12	−178.1 (2)	C13—N2—C14—C15	−177.7 (2)
N2—C14—C15—C16	1.5 (3)	C13—C8—C9—C10	1.8 (3)
N2—C14—C15—C20	−178.7 (2)	C14—N2—C13—C8	−145.5 (2)
C1—C2—C3—C4	0.6 (4)	C14—N2—C13—C12	38.9 (3)
C1—C6—C7—N1	−3.3 (3)	C14—C15—C16—O2	0.7 (4)
C2—C1—C6—C5	1.6 (3)	C14—C15—C16—C17	−179.2 (2)
C2—C1—C6—C7	−176.0 (2)	C14—C15—C20—C19	179.9 (2)
C2—C3—C4—I1	−177.29 (17)	C15—C16—C17—C18	−0.7 (4)
C2—C3—C4—C5	1.1 (3)	C16—C15—C20—C19	−0.3 (3)
C3—C4—C5—C6	−1.5 (3)	C16—C17—C18—C19	−0.2 (4)
C4—C5—C6—C1	0.1 (3)	C17—C18—C19—I2	−177.10 (17)
C4—C5—C6—C7	177.7 (2)	C17—C18—C19—C20	0.8 (4)
C5—C6—C7—N1	179.2 (2)	C18—C19—C20—C15	−0.6 (4)
C6—C1—C2—C3	−1.9 (3)	C20—C15—C16—O2	−179.1 (2)
C7—N1—C8—C9	29.0 (3)	C20—C15—C16—C17	1.0 (3)
C7—N1—C8—C13	−155.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···I2ⁱ	0.95	3.32	4.009 (2)	131
C5—H5···I2ⁱⁱ	0.95	3.17	4.061 (2)	156
C7—H7···I2ⁱⁱ	0.95	3.23	4.094 (2)	152
C18—H18···I1ⁱⁱⁱ	0.95	3.16	4.066 (2)	159
O1—H1···N1	0.84 (1)	1.84 (2)	2.609 (3)	152 (3)
O2—H2···N2	0.84 (1)	1.81 (2)	2.580 (3)	153 (3)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, −y+1/2, z+1/2; (iii) −x+1/2, −y, z−1/2.

Funding information

Funding for this research was provided by: Defense Threat Reduction Agency; Air Force Office of Scientific Research.

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