organic compounds
of 2,2′-bis[(2-chlorobenzyl)oxy]-1,1′-binaphthalene
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
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 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
|
Data collection: APEX2 (Bruker, 2008); cell 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
https://doi.org/10.1107/S2056989015014322/su5184sup1.cif
contains datablocks global, I. DOI: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
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
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).
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.
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
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).
For the synthesis and biological activity of naphthalene compounds, see: Upadhayaya et al. (2010); Rokade & Sayyed (2009). For the
of a very similar compound, 4,4'-{[[1,1'-binaphthalene]-2,2'-diylbis(oxy)]bis(methylene)}dibenzonitrile, see: Fu & Zhao (2007).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.
detailsCrystal data, data collection and structure
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 Uiso(H) = 1.2Ueq(C).Data collection: APEX2 (Bruker, 2008); cell
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).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). |
C34H24Cl2O2 | F(000) = 1112 |
Mr = 535.43 | Dx = 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 |
Bruker SMART APEXII CCD diffractometer | 4153 independent reflections |
Radiation source: fine-focus sealed tube | 3804 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ω and φ scans | θmax = 25.0°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −13→13 |
Tmin = 0.909, Tmax = 0.921 | k = −17→14 |
10688 measured reflections | l = −19→19 |
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(Fo2) + (0.0687P)2 + 1.4377P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
4153 reflections | Δρmax = 0.35 e Å−3 |
343 parameters | Δρmin = −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) |
C34H24Cl2O2 | V = 2668.19 (12) Å3 |
Mr = 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)° |
Bruker SMART APEXII CCD diffractometer | 4153 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 3804 reflections with I > 2σ(I) |
Tmin = 0.909, Tmax = 0.921 | Rint = 0.019 |
10688 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.116 | Δρmax = 0.35 e Å−3 |
S = 1.04 | Δρmin = −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 |
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. |
x | y | z | Uiso*/Ueq | ||
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) |
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) |
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) |
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. |
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
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fu, D.-W. & Zhao, H. (2007). Acta Cryst. E63, o3206. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rokade, Y. B. & Sayyed, R. Z. (2009). Rasayan J. Chem. 2, 972–980. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Upadhayaya, R. S., Vandavasi, J. K., Kardile, R. A., Lahore, S. V., Dixit, S. S., Deokar, H. S., Shinde, P. D., Sarmah, M. P. & Chattopadhyaya, J. (2010). Eur. J. Med. Chem. 45, 1854–1867. Web of Science CrossRef CAS PubMed Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.