Crystal structure of 2,2′-bis­[(2-chloro­benz­yl)­oxy]-1,1′-bi­naphthalene

Raja, R.; Jayanthi, M.; Rajakumar, P.; SubbiahPandi, A.

doi:10.1107/S2056989015014322

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 71| Part 9| September 2015| Pages o637-o638

https://doi.org/10.1107/S2056989015014322

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Crystal structure of 2,2′-bis[(2-chlorobenzyl)oxy]-1,1′-binaphthalene

Rajamani Raja,^a Mani Jayanthi,^b Perumal Rajakumar ^b and A. SubbiahPandi ^a ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy, Chennai-25, India
^*Correspondence e-mail: raja.13nap@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 29 July 2015; accepted 29 July 2015; online 6 August 2015)

In the title binaphthyl compound, C₃₄H₂₄Cl₂O₂, the dihedral angle between the two naphthyl ring systems (r.m.s. deviations = 0.016 and 0.035 Å) is 76.33 (8)°. The chlorophenyl rings make dihedral angles of 58.15 (12) and 76.21 (13)° with the naphthyl ring to which they are linked. The dihedral angle between the planes of the two chlorophenyl rings is 27.66 (16)°. In the crystal, C—H⋯O hydrogen bonds link molecules into chains propagating along [1-10]. The chains are linked by C—H⋯π interactions, forming a three-dimensional framework.

Keywords: crystal structure; binaphthyl; antimicrobials; antibiotic properties; minimum toxicity; hydrogen bonding.

CCDC reference: 1415827

1. Related literature

For the synthesis and biological activity of naphthalene compounds, see: Upadhayaya et al. (2010 ); Rokade & Sayyed (2009 ). For the crystal structure of a very similar compound, 4,4′-{[[1,1′-binaphthalene]-2,2′-diylbis(oxy)]bis(methylene)}dibenzonitrile, see: Fu & Zhao (2007 ).

2. Experimental

2.1. Crystal data

C₃₄H₂₄Cl₂O₂
M_r = 535.43
Monoclinic, C 2
a = 11.1983 (3) Å
b = 14.6094 (4) Å
c = 16.3263 (4) Å
β = 92.622 (2)°
V = 2668.19 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.25 mm

2.2. Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.909, T_max = 0.921
10688 measured reflections
4153 independent reflections
3804 reflections with I > 2σ(I)
R_int = 0.019

2.3. Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.116
S = 1.04
4153 reflections
343 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.47 e Å⁻³
Absolute structure: Flack (1983 ), 1709 (76%) Friedel pairs
Absolute structure parameter: −0.01 (8)

Table 1
Hydrogen-bond geometry (Å, °)

Cg5 is the centroid of the C19–C24 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22⋯O1ⁱ	0.93	2.57	3.413 (4)	151
C4—H4⋯Cg5ⁱⁱ	0.93	2.74	3.433 (4)	132
C33—H33⋯Cg5ⁱⁱⁱ	0.93	2.92	3.781 (6)	155
Symmetry codes: (i) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) -x+1, y, -z+2; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1415827

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015014322/su5184sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015014322/su5184Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015014322/su5184Isup3.cml

checkCIF report

Comment top

Naphthalene derivatives has been identified as new range of potent antimicrobials effective against a wide range of human pathogens. They occupy a central place among medicinally important compounds due to their diverse and interesting antibiotic properties with minimum toxicity (Rokade & Sayyed, 2009; Upadhayaya et al. 2010). Herein, we report on the synthesis and crystal structure of a new binaphthyl derivative.

The molecular structure of the title compound is shown in Fig. 1. The chlorophenyl ring (C1—C6) make a dihedral angle of 58.15 (12) ° with the naphthalene ring system (C8—C17), while the other chlorophenyl ring (C29—C34) makes a dihedral angle of 76.21 (13) ° with the naphthalene ring system (C18—C27). The two naphthalene rings are inclined to one another by 76.33 (8)° and the two chlorophenyl rings by 27.66 (16) °. Atoms O1 and O2 deviate from their respective naphthalene ring by 0.144 and 0.138 Å, respectively. The two naphthalene rings are connected at bond C17—C18, with torsion angle C19—C18—C17—C16 = 75.7 (3) °, indicating a (+) syn-clinal conformation for this group.

In the crystal, C—H···O hydrogen bonds link molecules into chains propagating along [110]; Table 1 and Fig. 2. The chains are linked by C—H···π interactions forming a three-dimensional framework (Table 1 and Fig. 3).

Synthesis and crystallization top

The title compound was synthesized by reacting two equivalents of 2-chloro benzylbromide with one equivalent of S-BINOL in dry DMF in the presence of K₂CO₃ at 333 K, which successfully provided the pure title product as a colourless solid. The product was dissolved in chloroform and heated for 2 min. The resulting solution was subjected to crystallization by slow evaporation of the solvent for 18 h resulting in the formation of single crystals.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The C-bound H atoms were positioned geometrically and allowed to ride on their parent atoms: C—H = 0.93 - 0.97 Å with U_iso(H) = 1.2U_eq(C).

Related literature top

For the synthesis and biological activity of naphthalene compounds, see: Upadhayaya et al. (2010); Rokade & Sayyed (2009). For the crystal structure of a very similar compound, 4,4'-{[[1,1'-binaphthalene]-2,2'-diylbis(oxy)]bis(methylene)}dibenzonitrile, see: Fu & Zhao (2007).

Structure description top

For the synthesis and biological activity of naphthalene compounds, see: Upadhayaya et al. (2010); Rokade & Sayyed (2009). For the crystal structure of a very similar compound, 4,4'-{[[1,1'-binaphthalene]-2,2'-diylbis(oxy)]bis(methylene)}dibenzonitrile, see: Fu & Zhao (2007).

Synthesis and crystallization top

Refinement details top

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. The intermolecular interactions are shown as dashed lines (see Table 1).
	Fig. 3. A partial view of the crystal packing of the title compound, showing the C—H···π interactions as dashed lines (see Table 1).

2,2'-Bis[(2-chlorobenzyl)oxy]-1,1'-binaphthalene top

Crystal data top

C₃₄H₂₄Cl₂O₂	F(000) = 1112
M_r = 535.43	D_x = 1.333 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 3804 reflections
a = 11.1983 (3) Å	θ = 1.3–25.0°
b = 14.6094 (4) Å	µ = 0.27 mm⁻¹
c = 16.3263 (4) Å	T = 293 K
β = 92.622 (2)°	Colourless, block
V = 2668.19 (12) Å³	0.35 × 0.30 × 0.25 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	4153 independent reflections
Radiation source: fine-focus sealed tube	3804 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω and φ scans	θ_max = 25.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→13
T_min = 0.909, T_max = 0.921	k = −17→14
10688 measured reflections	l = −19→19

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0687P)² + 1.4377P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
4153 reflections	Δρ_max = 0.35 e Å⁻³
343 parameters	Δρ_min = −0.47 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1709 (76%) Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (8)

Crystal data top

C₃₄H₂₄Cl₂O₂	V = 2668.19 (12) Å³
M_r = 535.43	Z = 4
Monoclinic, C2	Mo Kα radiation
a = 11.1983 (3) Å	µ = 0.27 mm⁻¹
b = 14.6094 (4) Å	T = 293 K
c = 16.3263 (4) Å	0.35 × 0.30 × 0.25 mm
β = 92.622 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4153 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3804 reflections with I > 2σ(I)
T_min = 0.909, T_max = 0.921	R_int = 0.019
10688 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.116	Δρ_max = 0.35 e Å⁻³
S = 1.04	Δρ_min = −0.47 e Å⁻³
4153 reflections	Absolute structure: Flack (1983), 1709 (76%) Friedel pairs
343 parameters	Absolute structure parameter: −0.01 (8)
1 restraint

Special details top

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

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

	x	y	z	U_iso*/U_eq
C1	0.3136 (3)	−0.1616 (2)	1.04240 (18)	0.0530 (8)
C2	0.2949 (3)	−0.1496 (3)	1.1254 (2)	0.0697 (10)
H2	0.2774	−0.1995	1.1581	0.084*
C3	0.3023 (3)	−0.0642 (3)	1.1581 (2)	0.0732 (12)
H3	0.2899	−0.0553	1.2135	0.088*
C4	0.3282 (3)	0.0083 (3)	1.1096 (2)	0.0662 (10)
H4	0.3338	0.0667	1.1321	0.079*
C5	0.3459 (2)	−0.0043 (2)	1.02794 (19)	0.0500 (7)
H5	0.3620	0.0464	0.9958	0.060*
C6	0.3408 (2)	−0.0892 (2)	0.99204 (15)	0.0375 (6)
C7	0.3671 (2)	−0.1012 (2)	0.90297 (15)	0.0420 (6)
H7A	0.4083	−0.0471	0.8845	0.050*
H7B	0.4204	−0.1529	0.8978	0.050*
C8	0.1865 (2)	−0.04007 (18)	0.84115 (14)	0.0317 (5)
C9	0.0865 (2)	−0.0367 (2)	0.88989 (15)	0.0419 (6)
H9	0.0759	−0.0815	0.9294	0.050*
C10	0.0050 (2)	0.0319 (2)	0.87954 (17)	0.0460 (7)
H10	−0.0599	0.0345	0.9131	0.055*
C11	0.0178 (2)	0.0992 (2)	0.81855 (16)	0.0399 (6)
C12	−0.0668 (3)	0.1700 (3)	0.80425 (19)	0.0544 (8)
H12	−0.1330	0.1731	0.8364	0.065*
C13	−0.0536 (3)	0.2330 (3)	0.7451 (2)	0.0618 (9)
H13	−0.1108	0.2786	0.7367	0.074*
C14	0.0464 (3)	0.2302 (2)	0.6959 (2)	0.0574 (8)
H14	0.0555	0.2741	0.6554	0.069*
C15	0.1301 (2)	0.1626 (2)	0.70786 (16)	0.0459 (7)
H15	0.1953	0.1607	0.6746	0.055*
C16	0.1197 (2)	0.09592 (18)	0.76940 (15)	0.0338 (6)
C17	0.20583 (19)	0.02472 (17)	0.78207 (13)	0.0297 (5)
C18	0.3126 (2)	0.02111 (17)	0.73118 (14)	0.0306 (5)
C19	0.4102 (2)	0.08223 (17)	0.74544 (14)	0.0312 (5)
C20	0.4120 (2)	0.14841 (19)	0.80899 (16)	0.0394 (6)
H20	0.3495	0.1504	0.8446	0.047*
C21	0.5042 (3)	0.2092 (2)	0.81876 (19)	0.0498 (7)
H21	0.5031	0.2525	0.8604	0.060*
C22	0.6005 (3)	0.2072 (2)	0.76682 (19)	0.0514 (8)
H22	0.6619	0.2498	0.7734	0.062*
C23	0.6040 (2)	0.1433 (2)	0.70721 (19)	0.0467 (7)
H23	0.6694	0.1412	0.6741	0.056*
C24	0.5096 (2)	0.07932 (18)	0.69410 (15)	0.0352 (6)
C25	0.5086 (2)	0.0147 (2)	0.62965 (16)	0.0415 (6)
H25	0.5737	0.0111	0.5964	0.050*
C26	0.4138 (2)	−0.0424 (2)	0.61550 (15)	0.0405 (6)
H26	0.4142	−0.0840	0.5725	0.049*
C27	0.3146 (2)	−0.03851 (18)	0.66597 (14)	0.0329 (5)
C28	0.2062 (3)	−0.15760 (19)	0.59124 (15)	0.0439 (6)
H28A	0.1470	−0.2029	0.6049	0.053*
H28B	0.2826	−0.1886	0.5894	0.053*
C29	0.1738 (2)	−0.1202 (2)	0.50774 (15)	0.0439 (7)
C30	0.1581 (3)	−0.0283 (3)	0.4912 (2)	0.0627 (9)
H30	0.1699	0.0149	0.5326	0.075*
C31	0.1242 (3)	−0.0006 (4)	0.4110 (3)	0.0882 (14)
H31	0.1137	0.0613	0.3996	0.106*
C32	0.1067 (4)	−0.0627 (5)	0.3502 (3)	0.1013 (19)
H32	0.0845	−0.0429	0.2975	0.122*
C33	0.1212 (4)	−0.1552 (5)	0.3653 (2)	0.0944 (17)
H33	0.1088	−0.1978	0.3234	0.113*
C34	0.1541 (3)	−0.1829 (3)	0.44307 (18)	0.0650 (10)
O1	0.26269 (16)	−0.11565 (12)	0.85074 (10)	0.0398 (4)
O2	0.21372 (16)	−0.09115 (14)	0.65440 (10)	0.0453 (5)
Cl1	0.30029 (15)	−0.27265 (8)	1.00356 (7)	0.1030 (4)
Cl2	0.16806 (12)	−0.29928 (8)	0.46325 (7)	0.0972 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0660 (18)	0.048 (2)	0.0444 (16)	−0.0107 (15)	−0.0038 (13)	0.0004 (14)
C2	0.076 (2)	0.091 (3)	0.0419 (17)	−0.019 (2)	0.0022 (15)	0.0106 (19)
C3	0.061 (2)	0.113 (4)	0.0459 (18)	−0.014 (2)	0.0050 (14)	−0.023 (2)
C4	0.0537 (17)	0.075 (3)	0.069 (2)	0.0005 (18)	−0.0026 (15)	−0.036 (2)
C5	0.0454 (15)	0.0470 (19)	0.0571 (17)	0.0010 (13)	−0.0038 (12)	−0.0084 (15)
C6	0.0331 (12)	0.0399 (16)	0.0389 (13)	0.0002 (11)	−0.0036 (9)	−0.0021 (12)
C7	0.0380 (13)	0.0483 (17)	0.0395 (13)	0.0013 (12)	−0.0008 (10)	0.0018 (13)
C8	0.0338 (12)	0.0331 (14)	0.0278 (11)	−0.0012 (10)	−0.0017 (9)	−0.0067 (11)
C9	0.0405 (14)	0.0537 (18)	0.0318 (12)	−0.0075 (13)	0.0040 (10)	0.0044 (13)
C10	0.0367 (13)	0.062 (2)	0.0399 (14)	−0.0019 (13)	0.0095 (11)	−0.0062 (14)
C11	0.0352 (12)	0.0509 (18)	0.0335 (13)	0.0045 (12)	−0.0001 (10)	−0.0082 (13)
C12	0.0400 (14)	0.070 (2)	0.0526 (17)	0.0163 (15)	0.0014 (12)	−0.0112 (18)
C13	0.0600 (19)	0.065 (2)	0.0600 (19)	0.0313 (17)	−0.0033 (14)	−0.0035 (18)
C14	0.0631 (19)	0.053 (2)	0.0561 (17)	0.0161 (16)	−0.0010 (14)	0.0084 (17)
C15	0.0478 (15)	0.0485 (17)	0.0416 (14)	0.0065 (13)	0.0038 (11)	0.0011 (14)
C16	0.0337 (12)	0.0377 (15)	0.0298 (12)	0.0013 (11)	−0.0016 (9)	−0.0073 (11)
C17	0.0312 (11)	0.0330 (14)	0.0246 (11)	−0.0028 (10)	−0.0012 (9)	−0.0065 (10)
C18	0.0340 (11)	0.0318 (14)	0.0259 (11)	0.0039 (10)	0.0008 (9)	0.0012 (10)
C19	0.0314 (11)	0.0304 (13)	0.0314 (12)	0.0008 (10)	−0.0014 (9)	0.0079 (11)
C20	0.0393 (13)	0.0381 (16)	0.0406 (13)	0.0018 (12)	0.0000 (10)	−0.0040 (12)
C21	0.0559 (17)	0.0396 (18)	0.0530 (16)	−0.0059 (13)	−0.0072 (13)	−0.0036 (14)
C22	0.0457 (15)	0.0444 (19)	0.0631 (18)	−0.0149 (13)	−0.0096 (13)	0.0092 (16)
C23	0.0364 (14)	0.0491 (18)	0.0545 (17)	−0.0068 (12)	0.0020 (11)	0.0156 (15)
C24	0.0360 (12)	0.0356 (14)	0.0340 (12)	0.0019 (11)	0.0008 (10)	0.0083 (11)
C25	0.0388 (13)	0.0454 (16)	0.0413 (14)	0.0044 (12)	0.0115 (10)	0.0063 (13)
C26	0.0523 (15)	0.0406 (16)	0.0291 (12)	0.0056 (13)	0.0073 (11)	−0.0045 (12)
C27	0.0373 (12)	0.0325 (14)	0.0288 (11)	−0.0028 (11)	0.0003 (9)	−0.0009 (11)
C28	0.0578 (16)	0.0390 (17)	0.0348 (13)	−0.0113 (13)	0.0007 (11)	−0.0080 (12)
C29	0.0383 (13)	0.059 (2)	0.0348 (13)	−0.0060 (12)	0.0038 (10)	−0.0006 (13)
C30	0.0557 (18)	0.068 (3)	0.064 (2)	0.0025 (16)	0.0019 (14)	0.0148 (19)
C31	0.069 (2)	0.108 (4)	0.088 (3)	0.017 (2)	0.007 (2)	0.043 (3)
C32	0.068 (2)	0.186 (6)	0.050 (2)	0.020 (3)	0.0014 (17)	0.028 (3)
C33	0.075 (2)	0.172 (6)	0.0352 (18)	−0.004 (3)	−0.0038 (16)	−0.014 (3)
C34	0.0510 (17)	0.105 (3)	0.0391 (15)	−0.0080 (18)	0.0078 (13)	−0.0074 (19)
O1	0.0474 (10)	0.0351 (11)	0.0365 (9)	0.0011 (8)	−0.0036 (7)	−0.0017 (8)
O2	0.0516 (10)	0.0506 (12)	0.0342 (9)	−0.0143 (9)	0.0077 (7)	−0.0180 (9)
Cl1	0.1870 (13)	0.0508 (6)	0.0725 (6)	−0.0226 (7)	0.0191 (7)	0.0005 (5)
Cl2	0.1348 (10)	0.0795 (8)	0.0790 (6)	−0.0275 (6)	0.0244 (6)	−0.0426 (6)

Geometric parameters (Å, º) top

C1—C6	1.382 (4)	C18—C27	1.377 (3)
C1—C2	1.392 (4)	C18—C19	1.422 (3)
C1—Cl1	1.746 (3)	C19—C20	1.418 (4)
C2—C3	1.357 (6)	C19—C24	1.424 (3)
C2—H2	0.9300	C20—C21	1.365 (4)
C3—C4	1.362 (6)	C20—H20	0.9300
C3—H3	0.9300	C21—C22	1.403 (4)
C4—C5	1.370 (5)	C21—H21	0.9300
C4—H4	0.9300	C22—C23	1.350 (4)
C5—C6	1.372 (4)	C22—H22	0.9300
C5—H5	0.9300	C23—C24	1.421 (4)
C6—C7	1.507 (3)	C23—H23	0.9300
C7—O1	1.431 (3)	C24—C25	1.413 (4)
C7—H7A	0.9700	C25—C26	1.361 (4)
C7—H7B	0.9700	C25—H25	0.9300
C8—C17	1.376 (3)	C26—C27	1.414 (3)
C8—O1	1.400 (3)	C26—H26	0.9300
C8—C9	1.404 (3)	C27—O2	1.373 (3)
C9—C10	1.361 (4)	C28—O2	1.416 (3)
C9—H9	0.9300	C28—C29	1.498 (4)
C10—C11	1.411 (4)	C28—H28A	0.9700
C10—H10	0.9300	C28—H28B	0.9700
C11—C12	1.414 (4)	C29—C30	1.379 (5)
C11—C16	1.426 (3)	C29—C34	1.408 (5)
C12—C13	1.348 (5)	C30—C31	1.405 (6)
C12—H12	0.9300	C30—H30	0.9300
C13—C14	1.408 (4)	C31—C32	1.353 (8)
C13—H13	0.9300	C31—H31	0.9300
C14—C15	1.369 (4)	C32—C33	1.382 (8)
C14—H14	0.9300	C32—H32	0.9300
C15—C16	1.408 (4)	C33—C34	1.367 (6)
C15—H15	0.9300	C33—H33	0.9300
C16—C17	1.427 (3)	C34—Cl2	1.737 (4)
C17—C18	1.488 (3)

C6—C1—C2	122.0 (3)	C27—C18—C17	119.7 (2)
C6—C1—Cl1	120.8 (2)	C19—C18—C17	121.2 (2)
C2—C1—Cl1	117.2 (3)	C20—C19—C18	122.2 (2)
C3—C2—C1	119.4 (4)	C20—C19—C24	117.7 (2)
C3—C2—H2	120.3	C18—C19—C24	120.0 (2)
C1—C2—H2	120.3	C21—C20—C19	121.0 (2)
C2—C3—C4	119.7 (3)	C21—C20—H20	119.5
C2—C3—H3	120.1	C19—C20—H20	119.5
C4—C3—H3	120.1	C20—C21—C22	120.9 (3)
C3—C4—C5	120.4 (4)	C20—C21—H21	119.5
C3—C4—H4	119.8	C22—C21—H21	119.5
C5—C4—H4	119.8	C23—C22—C21	119.9 (3)
C4—C5—C6	122.1 (3)	C23—C22—H22	120.0
C4—C5—H5	118.9	C21—C22—H22	120.0
C6—C5—H5	118.9	C22—C23—C24	121.2 (3)
C5—C6—C1	116.3 (2)	C22—C23—H23	119.4
C5—C6—C7	120.7 (3)	C24—C23—H23	119.4
C1—C6—C7	122.9 (3)	C25—C24—C23	122.2 (2)
O1—C7—C6	113.71 (19)	C25—C24—C19	118.6 (2)
O1—C7—H7A	108.8	C23—C24—C19	119.2 (2)
C6—C7—H7A	108.8	C26—C25—C24	121.0 (2)
O1—C7—H7B	108.8	C26—C25—H25	119.5
C6—C7—H7B	108.8	C24—C25—H25	119.5
H7A—C7—H7B	107.7	C25—C26—C27	120.3 (2)
C17—C8—O1	120.42 (19)	C25—C26—H26	119.9
C17—C8—C9	121.9 (2)	C27—C26—H26	119.9
O1—C8—C9	117.5 (2)	O2—C27—C18	114.76 (19)
C10—C9—C8	120.2 (2)	O2—C27—C26	124.1 (2)
C10—C9—H9	119.9	C18—C27—C26	121.1 (2)
C8—C9—H9	119.9	O2—C28—C29	114.6 (2)
C9—C10—C11	120.8 (2)	O2—C28—H28A	108.6
C9—C10—H10	119.6	C29—C28—H28A	108.6
C11—C10—H10	119.6	O2—C28—H28B	108.6
C10—C11—C12	122.5 (2)	C29—C28—H28B	108.6
C10—C11—C16	118.9 (2)	H28A—C28—H28B	107.6
C12—C11—C16	118.6 (3)	C30—C29—C34	118.2 (3)
C13—C12—C11	121.6 (3)	C30—C29—C28	123.9 (3)
C13—C12—H12	119.2	C34—C29—C28	117.9 (3)
C11—C12—H12	119.2	C29—C30—C31	119.3 (4)
C12—C13—C14	120.3 (3)	C29—C30—H30	120.3
C12—C13—H13	119.8	C31—C30—H30	120.3
C14—C13—H13	119.8	C32—C31—C30	120.9 (5)
C15—C14—C13	119.8 (3)	C32—C31—H31	119.5
C15—C14—H14	120.1	C30—C31—H31	119.5
C13—C14—H14	120.1	C31—C32—C33	120.9 (4)
C14—C15—C16	121.5 (3)	C31—C32—H32	119.6
C14—C15—H15	119.3	C33—C32—H32	119.6
C16—C15—H15	119.3	C34—C33—C32	118.7 (5)
C15—C16—C11	118.2 (2)	C34—C33—H33	120.7
C15—C16—C17	122.0 (2)	C32—C33—H33	120.7
C11—C16—C17	119.7 (2)	C33—C34—C29	122.0 (5)
C8—C17—C16	118.4 (2)	C33—C34—Cl2	118.9 (4)
C8—C17—C18	121.6 (2)	C29—C34—Cl2	119.0 (2)
C16—C17—C18	120.0 (2)	C8—O1—C7	115.3 (2)
C27—C18—C19	119.0 (2)	C27—O2—C28	120.38 (19)

C6—C1—C2—C3	0.6 (5)	C17—C18—C19—C20	1.0 (4)
Cl1—C1—C2—C3	−179.0 (3)	C27—C18—C19—C24	−1.8 (3)
C1—C2—C3—C4	−0.1 (5)	C17—C18—C19—C24	−177.9 (2)
C2—C3—C4—C5	0.4 (5)	C18—C19—C20—C21	−176.8 (3)
C3—C4—C5—C6	−1.2 (5)	C24—C19—C20—C21	2.1 (4)
C4—C5—C6—C1	1.6 (4)	C19—C20—C21—C22	−0.8 (4)
C4—C5—C6—C7	−176.8 (3)	C20—C21—C22—C23	−1.3 (4)
C2—C1—C6—C5	−1.3 (4)	C21—C22—C23—C24	2.0 (4)
Cl1—C1—C6—C5	178.3 (2)	C22—C23—C24—C25	176.9 (3)
C2—C1—C6—C7	177.0 (3)	C22—C23—C24—C19	−0.6 (4)
Cl1—C1—C6—C7	−3.4 (4)	C20—C19—C24—C25	−179.1 (2)
C5—C6—C7—O1	−104.8 (3)	C18—C19—C24—C25	−0.2 (4)
C1—C6—C7—O1	77.0 (3)	C20—C19—C24—C23	−1.4 (3)
C17—C8—C9—C10	0.0 (4)	C18—C19—C24—C23	177.5 (2)
O1—C8—C9—C10	−175.7 (2)	C23—C24—C25—C26	−176.2 (3)
C8—C9—C10—C11	1.7 (4)	C19—C24—C25—C26	1.4 (4)
C9—C10—C11—C12	178.1 (3)	C24—C25—C26—C27	−0.7 (4)
C9—C10—C11—C16	−1.9 (4)	C19—C18—C27—O2	−176.5 (2)
C10—C11—C12—C13	−179.2 (3)	C17—C18—C27—O2	−0.4 (3)
C16—C11—C12—C13	0.8 (4)	C19—C18—C27—C26	2.7 (4)
C11—C12—C13—C14	−0.4 (5)	C17—C18—C27—C26	178.8 (2)
C12—C13—C14—C15	0.5 (5)	C25—C26—C27—O2	177.7 (2)
C13—C14—C15—C16	−0.9 (5)	C25—C26—C27—C18	−1.4 (4)
C14—C15—C16—C11	1.2 (4)	O2—C28—C29—C30	3.2 (4)
C14—C15—C16—C17	179.5 (3)	O2—C28—C29—C34	−174.4 (2)
C10—C11—C16—C15	178.9 (3)	C34—C29—C30—C31	−0.5 (4)
C12—C11—C16—C15	−1.1 (4)	C28—C29—C30—C31	−178.1 (3)
C10—C11—C16—C17	0.6 (4)	C29—C30—C31—C32	0.1 (5)
C12—C11—C16—C17	−179.4 (2)	C30—C31—C32—C33	0.2 (6)
O1—C8—C17—C16	174.3 (2)	C31—C32—C33—C34	−0.2 (6)
C9—C8—C17—C16	−1.4 (3)	C32—C33—C34—C29	−0.2 (6)
O1—C8—C17—C18	−4.9 (3)	C32—C33—C34—Cl2	178.0 (3)
C9—C8—C17—C18	179.4 (2)	C30—C29—C34—C33	0.5 (4)
C15—C16—C17—C8	−177.2 (2)	C28—C29—C34—C33	178.3 (3)
C11—C16—C17—C8	1.0 (3)	C30—C29—C34—Cl2	−177.7 (2)
C15—C16—C17—C18	2.0 (3)	C28—C29—C34—Cl2	0.1 (3)
C11—C16—C17—C18	−179.8 (2)	C17—C8—O1—C7	86.3 (3)
C8—C17—C18—C27	78.8 (3)	C9—C8—O1—C7	−97.9 (3)
C16—C17—C18—C27	−100.4 (3)	C6—C7—O1—C8	68.7 (3)
C8—C17—C18—C19	−105.2 (3)	C18—C27—O2—C28	−177.7 (2)
C16—C17—C18—C19	75.6 (3)	C26—C27—O2—C28	3.2 (4)
C27—C18—C19—C20	177.0 (2)	C29—C28—O2—C27	−80.7 (3)

Hydrogen-bond geometry (Å, º) top

Cg5 is the centroid of the C19–C24 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···O1ⁱ	0.93	2.57	3.413 (4)	151
C4—H4···Cg5ⁱⁱ	0.93	2.74	3.433 (4)	132
C33—H33···Cg5ⁱⁱⁱ	0.93	2.92	3.781 (6)	155

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

Hydrogen-bond geometry (Å, º) top

Cg5 is the centroid of the C19–C24 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···O1ⁱ	0.93	2.57	3.413 (4)	151
C4—H4···Cg5ⁱⁱ	0.93	2.74	3.433 (4)	132
C33—H33···Cg5ⁱⁱⁱ	0.93	2.92	3.781 (6)	155

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

Acknowledgements

RR and ASP thank the Department of Chemistry, IIT, Chennai, India, for the X-ray data collection.

References

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Volume 71| Part 9| September 2015| Pages o637-o638

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