[3,4-Bis(2,3-di­chloro­phen­yl)cyclo­butane-1,2-di­yl]bis­(furan-2-yl­methanone) monohydrate

Renuka, N.; Naveen, S.; Raghavendra, K.R.; Dileep Kumar, A.; Lokanath, N.K.; Ajay Kumar, K.

doi:10.1107/S2414314617003182

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 3| March 2017| x170318

https://doi.org/10.1107/S2414314617003182

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[3,4-Bis(2,3-dichlorophenyl)cyclobutane-1,2-diyl]bis(furan-2-ylmethanone) monohydrate

N. Renuka,^a S. Naveen,^b K. R. Raghavendra,^c A. Dileep Kumar,^d N. K. Lokanath ^e ^* and K. Ajay Kumar ^d ^*

^aDepartment of Chemistry, GSSS Institute of Engineering and Technology For Women, Visveswaraya Technological University, Mysuru 570 016, India, ^bInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru 570 006, India, ^cDepartment of Chemistry, SBRR Mahajana College, Mysuru 570 006, India, ^dDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysuru 570 005, India, and ^eDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru 570 006, India
^*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in, ajaykumar@ycm.uni-mysore.ac.in

Edited by J. Simpson, University of Otago, New Zealand (Received 14 February 2017; accepted 27 February 2017; online 10 March 2017)

In the title hydrate, C₂₆H₁₆Cl₄O₄·H₂O, the cyclobutane ring carries two 2,3-dichlorophenyl and two furan-2-ylmethanone substituents. It subtends dihedral angles of 86.6 (3) and 37.3 (3)° with the furan rings and 77.0 (5) and 77.0 (3)° with the dichlorophenyl rings. In the crystal, molecules are linked via weak C—H⋯O hydrogen bonds, forming chains propagating along the a-axis direction. Additional C—H⋯O and C—H⋯Cl hydrogen bonds generate a three-dimensional network of molecules stacked along the b axis.

Keywords: crystal structure; hydrogen bonding; cyclobutane.

CCDC reference: 1534887

Structure description

Recently, a new route to polysubstituted cyclobutanes via a K₂S₂O₈-promoted intramolecular [2 + 2]-cycloaddition (Zhu et al., 2016 ) and an efficient intermolecular [2 + 2]-cycloaddition (Raghavendra et al., 2017 ) were reported. We herein report the synthesis and crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The dihedral angles between the central cyclobutane ring and the two furan rings (O1/C1–C4 and O3/C14–C17) bridged by the carbonyl group are 86.6 (3) and 37.3 (3)°, respectively, whereas the two dichlorophenyl rings subtend angles of 77.0 (5) and 77.0 (3)°, respectively, with the cyclobutane ring. The furan rings are inclined at 68.6 (3)° to one another while the angle between the two dichlorophenyl rings is 40.8 (2)°. The carbonyl substituents at C5 and C18 on the (O1/C1–C4 and O3/C14–C17) furan rings lie close to the ring planes, as indicated by the torsion angles O1—C4—C5—O2 = 2.6 (6)° and O3—C17—C18—O4 = −179.0 (4)°.

Figure 1
The molecular structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.

In the crystal, molecules are linked via weak C—H⋯O hydrogen bonds (Table 1), forming chains propagating along the a-axis direction (Fig. 2). Additional C—H⋯O and C—H⋯Cl hydrogen bonds generate a three-dimensional network of molecules stacked along the b axis (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O4ⁱ	0.93	2.54	3.424 (7)	159
C9—H9⋯O2ⁱⁱ	0.93	2.48	3.184 (6)	133
C19—H19⋯O2ⁱⁱ	0.98	2.41	3.267 (5)	146
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Figure 2
C—H⋯O hydrogen bonds forming chains propagating along the b-axis direction. Hydrogen bonds are shown as dashed lines.

Figure 3
C—H⋯O and C—H⋯Cl hydrogen bonds generating a three-dimensional network of molecules stacked along the b axis. Hydrogen bonds are shown as dashed lines.

Synthesis and crystallization

A mixture of 2,3-dichlorobenzaldehyde (5 mmol), 2-acetylfuran (5 mmol) and sodium hydroxide (5 mmol) in 95% ethanol (25 ml) was refluxed on a water bath for 2 h. The progress of the reaction was monitored by TLC. After the completion of the reaction, the mixture was poured into ice-cold water and kept in a refrigerator overnight. The solid formed was filtered, and washed with cold hydrochloric acid (5%). Yellow rectangular crystals were obtained from 60% aqueous methanol solution by slow evaporation (yield 82%, m.p. 391–393 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₆H₁₆Cl₄O₄·H₂O
M_r	552.20
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	10.9673 (12), 20.211 (2), 22.491 (2)
V (Å³)	4985.4 (9)
Z	8
Radiation type	Cu Kα
μ (mm⁻¹)	4.63
Crystal size (mm)	0.28 × 0.26 × 0.24

Data collection
Diffractometer	Bruker X8 Proteum
Absorption correction	Multi-scan (SADABS; Bruker, 2013 )
T_min, T_max	0.357, 0.403
No. of measured, independent and observed [I > 2σ(I)] reflections	25946, 4144, 2605
R_int	0.110
(sin θ/λ)_max (Å⁻¹)	0.587

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.184, 1.03
No. of reflections	4144
No. of parameters	320
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.31
Computer programs: APEX2 and SAINT (Bruker, 2013), SHELXS97 and SHELXL97 (Sheldrick, 2008 ), Mercury (Macrae et al., 2008 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1534887

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617003182/sj4091sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S2414314617003182/sj4091Isup2.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

(3,4-bis(2,3-dichlorophenyl)cyclobutane-1,2-diyl)bis(furan-2-ylmethanone) hydrate top

Crystal data top

C₂₆H₁₆Cl₄O₄·H₂O	F(000) = 2256
M_r = 552.20	D_x = 1.471 Mg m⁻³
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2605 reflections
a = 10.9673 (12) Å	θ = 4.8–64.8°
b = 20.211 (2) Å	µ = 4.63 mm⁻¹
c = 22.491 (2) Å	T = 296 K
V = 4985.4 (9) Å³	Rectangle, yellow
Z = 8	0.28 × 0.26 × 0.24 mm

Data collection top

Bruker X8 Proteum diffractometer	4144 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2605 reflections with I > 2σ(I)
Helios multilayer optics monochromator	R_int = 0.110
Detector resolution: 18.4 pixels mm^-1	θ_max = 64.7°, θ_min = 4.8°
φ and ω scans	h = −12→10
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −23→23
T_min = 0.357, T_max = 0.403	l = −26→24
25946 measured reflections

Refinement top

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)] = 0.062	H-atom parameters constrained
wR(F²) = 0.184	w = 1/[σ²(F_o²) + (0.0851P)² + 1.6075P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4144 reflections	Δρ_max = 0.36 e Å⁻³
320 parameters	Δρ_min = −0.31 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0025 (2)

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.45306 (10)	0.30473 (6)	0.45130 (6)	0.0683 (4)
Cl2	0.63057 (13)	0.30057 (8)	0.55980 (6)	0.0851 (5)
Cl3	0.40331 (10)	0.18694 (6)	0.33566 (7)	0.0753 (5)
Cl4	0.53084 (17)	0.07000 (7)	0.40060 (9)	0.1110 (7)
O1	0.3358 (3)	0.52823 (15)	0.24221 (15)	0.0638 (11)
O2	0.4107 (3)	0.40209 (15)	0.22127 (15)	0.0623 (11)
O3	0.6993 (3)	0.43530 (18)	0.16593 (15)	0.0747 (12)
O4	0.5712 (3)	0.27567 (16)	0.17591 (15)	0.0740 (12)
C1	0.3265 (5)	0.5923 (3)	0.2602 (3)	0.076 (2)
C2	0.4214 (5)	0.6099 (3)	0.2929 (3)	0.078 (2)
C3	0.4973 (4)	0.5542 (2)	0.2967 (2)	0.0680 (19)
C4	0.4428 (4)	0.5049 (2)	0.2654 (2)	0.0507 (14)
C5	0.4746 (3)	0.4370 (2)	0.25304 (19)	0.0487 (12)
C6	0.5854 (3)	0.40991 (19)	0.28332 (19)	0.0473 (14)
C7	0.5482 (3)	0.3692 (2)	0.33959 (18)	0.0456 (11)
C8	0.6285 (3)	0.3744 (2)	0.39355 (18)	0.0467 (12)
C9	0.7404 (4)	0.4062 (2)	0.3933 (2)	0.0557 (16)
C10	0.8164 (4)	0.4050 (3)	0.4419 (2)	0.0687 (17)
C11	0.7832 (4)	0.3727 (3)	0.4929 (2)	0.0730 (19)
C12	0.6713 (4)	0.3412 (2)	0.49532 (19)	0.0593 (17)
C13	0.5936 (4)	0.3428 (2)	0.44642 (19)	0.0503 (14)
C14	0.7232 (5)	0.4715 (3)	0.1170 (3)	0.085 (2)
C15	0.6914 (5)	0.4393 (3)	0.0684 (3)	0.083 (2)
C16	0.6448 (5)	0.3776 (3)	0.0870 (2)	0.0723 (19)
C17	0.6498 (4)	0.3768 (2)	0.1469 (2)	0.0567 (16)
C18	0.6140 (4)	0.3287 (2)	0.1908 (2)	0.0540 (14)
C19	0.6361 (3)	0.34523 (19)	0.25510 (18)	0.0463 (12)
C20	0.5666 (3)	0.30417 (19)	0.30123 (18)	0.0448 (11)
C21	0.6263 (3)	0.2453 (2)	0.33068 (19)	0.0497 (14)
C22	0.7508 (4)	0.2449 (2)	0.3429 (2)	0.0617 (16)
C23	0.8034 (5)	0.1936 (3)	0.3734 (3)	0.082 (2)
C24	0.7369 (6)	0.1410 (3)	0.3914 (3)	0.086 (2)
C25	0.6137 (5)	0.1381 (2)	0.3792 (2)	0.072 (2)
C26	0.5583 (4)	0.1908 (2)	0.3490 (2)	0.0553 (14)
O5	0.4797 (7)	0.4741 (4)	0.5418 (5)	0.210 (5)
H1	0.26180	0.62010	0.25080	0.0910*
H2	0.43510	0.65110	0.31000	0.0930*
H3	0.57120	0.55150	0.31690	0.0820*
H6	0.64820	0.44330	0.29110	0.0570*
H7	0.46220	0.37600	0.34970	0.0550*
H9	0.76480	0.42890	0.35930	0.0670*
H10	0.89130	0.42650	0.44020	0.0820*
H11	0.83520	0.37190	0.52560	0.0870*
H14	0.75750	0.51350	0.11740	0.1020*
H15	0.69840	0.45430	0.02950	0.1000*
H16	0.61600	0.34390	0.06260	0.0870*
H19	0.72370	0.34220	0.26330	0.0560*
H20	0.48800	0.29060	0.28450	0.0540*
H22	0.79900	0.28000	0.33010	0.0740*
H23	0.88630	0.19500	0.38190	0.0980*
H24	0.77430	0.10660	0.41200	0.1030*
H5A	0.40680	0.48360	0.55150	0.3150*
H5B	0.48290	0.43430	0.52980	0.3150*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0594 (6)	0.0815 (8)	0.0641 (8)	−0.0145 (5)	0.0089 (5)	0.0080 (6)
Cl2	0.0958 (9)	0.1063 (11)	0.0533 (8)	−0.0027 (8)	−0.0004 (6)	0.0212 (7)
Cl3	0.0603 (7)	0.0729 (8)	0.0927 (10)	−0.0198 (6)	0.0031 (6)	0.0031 (7)
Cl4	0.1362 (13)	0.0602 (8)	0.1365 (16)	0.0082 (8)	0.0522 (11)	0.0300 (9)
O1	0.0601 (18)	0.0644 (19)	0.067 (2)	0.0081 (14)	−0.0037 (15)	0.0059 (16)
O2	0.0562 (16)	0.0627 (19)	0.068 (2)	−0.0027 (14)	−0.0140 (16)	−0.0085 (16)
O3	0.086 (2)	0.078 (2)	0.060 (2)	−0.0212 (18)	−0.0029 (17)	0.0087 (18)
O4	0.103 (2)	0.060 (2)	0.059 (2)	−0.0121 (18)	0.0065 (18)	−0.0118 (17)
C1	0.089 (4)	0.062 (3)	0.076 (4)	0.022 (3)	0.011 (3)	0.005 (3)
C2	0.103 (4)	0.057 (3)	0.074 (4)	0.004 (3)	0.002 (3)	−0.004 (3)
C3	0.073 (3)	0.061 (3)	0.070 (4)	0.000 (2)	−0.005 (3)	−0.006 (2)
C4	0.051 (2)	0.053 (2)	0.048 (3)	0.0021 (19)	0.0017 (19)	0.005 (2)
C5	0.048 (2)	0.056 (2)	0.042 (2)	−0.0055 (19)	0.0027 (19)	−0.0005 (19)
C6	0.047 (2)	0.046 (2)	0.049 (3)	−0.0056 (17)	0.0006 (19)	−0.0021 (19)
C7	0.0397 (19)	0.054 (2)	0.043 (2)	−0.0005 (17)	0.0027 (17)	0.0014 (19)
C8	0.050 (2)	0.053 (2)	0.037 (2)	−0.0011 (18)	0.0017 (18)	−0.0020 (18)
C9	0.048 (2)	0.072 (3)	0.047 (3)	−0.006 (2)	0.003 (2)	0.003 (2)
C10	0.058 (3)	0.082 (3)	0.066 (3)	−0.011 (2)	−0.007 (2)	0.004 (3)
C11	0.061 (3)	0.097 (4)	0.061 (3)	−0.007 (3)	−0.012 (2)	0.003 (3)
C12	0.069 (3)	0.070 (3)	0.039 (3)	0.003 (2)	0.001 (2)	0.003 (2)
C13	0.049 (2)	0.055 (2)	0.047 (3)	−0.0016 (19)	−0.0003 (19)	−0.006 (2)
C14	0.096 (4)	0.083 (4)	0.077 (4)	−0.022 (3)	0.007 (3)	0.025 (3)
C15	0.095 (4)	0.100 (4)	0.055 (4)	0.006 (3)	0.009 (3)	0.015 (3)
C16	0.086 (3)	0.081 (4)	0.050 (3)	0.000 (3)	0.004 (3)	−0.006 (3)
C17	0.058 (2)	0.065 (3)	0.047 (3)	0.000 (2)	0.002 (2)	−0.004 (2)
C18	0.058 (2)	0.051 (2)	0.053 (3)	0.002 (2)	0.005 (2)	−0.002 (2)
C19	0.046 (2)	0.047 (2)	0.046 (2)	−0.0033 (17)	0.0017 (18)	−0.0003 (18)
C20	0.0413 (19)	0.046 (2)	0.047 (2)	−0.0066 (16)	−0.0023 (17)	−0.0007 (18)
C21	0.052 (2)	0.046 (2)	0.051 (3)	−0.0011 (18)	−0.0004 (19)	−0.0009 (19)
C22	0.052 (2)	0.067 (3)	0.066 (3)	0.002 (2)	−0.002 (2)	−0.001 (2)
C23	0.066 (3)	0.098 (4)	0.081 (4)	0.024 (3)	−0.010 (3)	0.008 (3)
C24	0.090 (4)	0.079 (4)	0.089 (4)	0.032 (3)	0.012 (3)	0.023 (3)
C25	0.091 (4)	0.050 (3)	0.074 (4)	0.009 (2)	0.022 (3)	0.009 (2)
C26	0.056 (2)	0.053 (2)	0.057 (3)	−0.0014 (19)	0.005 (2)	−0.002 (2)
O5	0.172 (6)	0.142 (6)	0.316 (12)	0.016 (5)	0.032 (7)	−0.107 (7)

Geometric parameters (Å, º) top

Cl1—C13	1.726 (4)	C15—C16	1.411 (8)
Cl2—C12	1.725 (4)	C16—C17	1.348 (6)
Cl3—C26	1.728 (5)	C17—C18	1.440 (6)
Cl4—C25	1.718 (5)	C18—C19	1.504 (6)
O1—C1	1.361 (7)	C19—C20	1.532 (5)
O1—C4	1.368 (5)	C20—C21	1.511 (5)
O2—C5	1.225 (5)	C21—C26	1.393 (6)
O3—C14	1.347 (7)	C21—C22	1.393 (6)
O3—C17	1.370 (5)	C22—C23	1.371 (7)
O4—C18	1.217 (5)	C23—C24	1.351 (9)
O5—H5B	0.8500	C24—C25	1.380 (9)
O5—H5A	0.8500	C25—C26	1.402 (6)
C1—C2	1.323 (8)	C1—H1	0.9300
C2—C3	1.403 (7)	C2—H2	0.9300
C3—C4	1.359 (6)	C3—H3	0.9300
C4—C5	1.443 (6)	C6—H6	0.9800
C5—C6	1.497 (5)	C7—H7	0.9800
C6—C7	1.564 (6)	C9—H9	0.9300
C6—C19	1.556 (5)	C10—H10	0.9300
C7—C20	1.585 (6)	C11—H11	0.9300
C7—C8	1.503 (5)	C14—H14	0.9300
C8—C9	1.385 (6)	C15—H15	0.9300
C8—C13	1.403 (6)	C16—H16	0.9300
C9—C10	1.375 (6)	C19—H19	0.9800
C10—C11	1.369 (7)	C20—H20	0.9800
C11—C12	1.384 (6)	C22—H22	0.9300
C12—C13	1.392 (6)	C23—H23	0.9300
C14—C15	1.319 (9)	C24—H24	0.9300

C1—O1—C4	106.2 (4)	C22—C21—C26	117.5 (4)
C14—O3—C17	106.9 (4)	C21—C22—C23	121.1 (4)
H5A—O5—H5B	110.00	C22—C23—C24	121.2 (5)
O1—C1—C2	111.2 (5)	C23—C24—C25	120.2 (6)
C1—C2—C3	106.6 (5)	Cl4—C25—C24	119.8 (4)
C2—C3—C4	107.2 (4)	C24—C25—C26	119.2 (4)
O1—C4—C3	108.8 (4)	Cl4—C25—C26	121.0 (4)
O1—C4—C5	117.5 (4)	Cl3—C26—C21	120.7 (3)
C3—C4—C5	133.7 (4)	C21—C26—C25	120.8 (4)
O2—C5—C6	121.3 (4)	Cl3—C26—C25	118.4 (3)
C4—C5—C6	117.2 (3)	O1—C1—H1	124.00
O2—C5—C4	121.5 (4)	C2—C1—H1	124.00
C5—C6—C19	114.3 (3)	C3—C2—H2	127.00
C7—C6—C19	88.9 (3)	C1—C2—H2	127.00
C5—C6—C7	110.4 (3)	C2—C3—H3	126.00
C6—C7—C20	87.9 (3)	C4—C3—H3	126.00
C8—C7—C20	115.0 (3)	C7—C6—H6	114.00
C6—C7—C8	117.6 (3)	C19—C6—H6	114.00
C7—C8—C9	123.2 (4)	C5—C6—H6	114.00
C7—C8—C13	119.5 (3)	C6—C7—H7	111.00
C9—C8—C13	117.2 (4)	C8—C7—H7	112.00
C8—C9—C10	121.7 (4)	C20—C7—H7	111.00
C9—C10—C11	120.9 (4)	C8—C9—H9	119.00
C10—C11—C12	119.2 (4)	C10—C9—H9	119.00
Cl2—C12—C13	121.1 (3)	C11—C10—H10	119.00
C11—C12—C13	120.1 (4)	C9—C10—H10	120.00
Cl2—C12—C11	118.8 (3)	C10—C11—H11	120.00
Cl1—C13—C12	119.1 (3)	C12—C11—H11	120.00
C8—C13—C12	120.9 (4)	C15—C14—H14	124.00
Cl1—C13—C8	120.0 (3)	O3—C14—H14	125.00
O3—C14—C15	111.0 (5)	C14—C15—H15	127.00
C14—C15—C16	106.6 (6)	C16—C15—H15	127.00
C15—C16—C17	107.0 (5)	C17—C16—H16	126.00
O3—C17—C18	118.5 (4)	C15—C16—H16	127.00
C16—C17—C18	133.0 (4)	C6—C19—H19	109.00
O3—C17—C16	108.5 (4)	C18—C19—H19	109.00
O4—C18—C17	120.7 (4)	C20—C19—H19	109.00
C17—C18—C19	117.7 (4)	C7—C20—H20	109.00
O4—C18—C19	121.5 (4)	C19—C20—H20	109.00
C6—C19—C18	121.4 (3)	C21—C20—H20	109.00
C18—C19—C20	116.8 (3)	C23—C22—H22	120.00
C6—C19—C20	90.1 (3)	C21—C22—H22	119.00
C7—C20—C19	89.0 (3)	C22—C23—H23	119.00
C7—C20—C21	118.0 (3)	C24—C23—H23	119.00
C19—C20—C21	120.5 (3)	C23—C24—H24	120.00
C20—C21—C22	121.1 (3)	C25—C24—H24	120.00
C20—C21—C26	121.4 (3)

C4—O1—C1—C2	0.2 (6)	C9—C10—C11—C12	−0.3 (8)
C1—O1—C4—C3	−0.2 (5)	C10—C11—C12—Cl2	179.9 (4)
C1—O1—C4—C5	179.7 (4)	C10—C11—C12—C13	−0.3 (7)
C17—O3—C14—C15	0.2 (6)	Cl2—C12—C13—Cl1	1.3 (5)
C14—O3—C17—C16	0.5 (5)	Cl2—C12—C13—C8	−178.3 (3)
C14—O3—C17—C18	−179.2 (4)	C11—C12—C13—Cl1	−178.5 (4)
O1—C1—C2—C3	−0.1 (7)	C11—C12—C13—C8	1.9 (7)
C1—C2—C3—C4	0.0 (6)	O3—C14—C15—C16	−0.7 (6)
C2—C3—C4—O1	0.1 (5)	C14—C15—C16—C17	0.9 (6)
C2—C3—C4—C5	−179.7 (5)	C15—C16—C17—O3	−0.8 (6)
O1—C4—C5—O2	2.6 (6)	C15—C16—C17—C18	178.8 (5)
O1—C4—C5—C6	−174.2 (4)	O3—C17—C18—O4	−179.0 (4)
C3—C4—C5—O2	−177.6 (5)	O3—C17—C18—C19	−1.4 (6)
C3—C4—C5—C6	5.6 (7)	C16—C17—C18—O4	1.5 (8)
O2—C5—C6—C7	−78.4 (5)	C16—C17—C18—C19	179.0 (5)
O2—C5—C6—C19	20.1 (5)	O4—C18—C19—C6	−127.4 (4)
C4—C5—C6—C7	98.4 (4)	O4—C18—C19—C20	−19.4 (6)
C4—C5—C6—C19	−163.2 (3)	C17—C18—C19—C6	55.1 (5)
C5—C6—C7—C8	−142.2 (3)	C17—C18—C19—C20	163.1 (4)
C5—C6—C7—C20	100.6 (3)	C6—C19—C20—C7	−15.4 (3)
C19—C6—C7—C8	102.2 (3)	C6—C19—C20—C21	−137.7 (4)
C19—C6—C7—C20	−15.1 (2)	C18—C19—C20—C7	−141.1 (3)
C5—C6—C19—C18	25.5 (5)	C18—C19—C20—C21	96.5 (4)
C5—C6—C19—C20	−96.4 (3)	C7—C20—C21—C22	−73.1 (5)
C7—C6—C19—C18	137.5 (3)	C7—C20—C21—C26	104.0 (4)
C7—C6—C19—C20	15.6 (3)	C19—C20—C21—C22	33.8 (6)
C6—C7—C8—C9	−8.5 (6)	C19—C20—C21—C26	−149.1 (4)
C6—C7—C8—C13	175.1 (3)	C20—C21—C22—C23	175.3 (5)
C20—C7—C8—C9	92.9 (5)	C26—C21—C22—C23	−1.9 (7)
C20—C7—C8—C13	−83.5 (4)	C20—C21—C26—Cl3	2.9 (6)
C6—C7—C20—C19	15.3 (2)	C20—C21—C26—C25	−176.5 (4)
C6—C7—C20—C21	139.8 (3)	C22—C21—C26—Cl3	−179.9 (3)
C8—C7—C20—C19	−104.4 (3)	C22—C21—C26—C25	0.7 (6)
C8—C7—C20—C21	20.1 (4)	C21—C22—C23—C24	1.6 (9)
C7—C8—C9—C10	−174.1 (4)	C22—C23—C24—C25	0.0 (10)
C13—C8—C9—C10	2.3 (6)	C23—C24—C25—Cl4	178.3 (5)
C7—C8—C13—Cl1	−5.9 (5)	C23—C24—C25—C26	−1.2 (9)
C7—C8—C13—C12	173.7 (4)	Cl4—C25—C26—Cl3	1.9 (5)
C9—C8—C13—Cl1	177.6 (3)	Cl4—C25—C26—C21	−178.7 (3)
C9—C8—C13—C12	−2.9 (6)	C24—C25—C26—Cl3	−178.6 (4)
C8—C9—C10—C11	−0.8 (8)	C24—C25—C26—C21	0.8 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4ⁱ	0.93	2.54	3.424 (7)	159
C9—H9···O2ⁱⁱ	0.93	2.48	3.184 (6)	133
C19—H19···O2ⁱⁱ	0.98	2.41	3.267 (5)	146

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

Acknowledgements

The authors are grateful to the Institution of Excellence, Vijnana Bhavana, University of Mysore, India, for providing the single-crystal X-ray diffractometer facility.

References

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