organic compounds
6,7-Dimethoxy-2,4-diphenylquinoline
aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and bDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India
*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in
In the title structure of the title compound, C23H19NO2, two conformationally similar molecules (A and B) comprise the The dihedral angle between phenyl rings bridged by the quinoline moiety are 76.25 (8)° in molecule A and 70.39 (9)° in molecule B. In the crystal, the independent molecules are connected by C—H⋯O hydrogen bonds and the resulting dimeric aggregates are linked by π–π [inter-centroid distance = 3.7370 (8) Å] and C—H⋯π interactions, forming a three-dimensional architecture.
CCDC reference: 981089
Related literature
For general background, and the biological and pharmacological properties of quinoline derivatives, see: Michael (2006). For a related structure, see: Prabhuswamy et al. (2012).
Experimental
Crystal data
|
Data collection: APEX2 (Bruker, 2013); cell SAINT-Plus (Bruker, 2013); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
CCDC reference: 981089
10.1107/S1600536814000725/tk5285sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814000725/tk5285Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814000725/tk5285Isup3.cml
The enaminone (Z)-3((3,4-dimethoxyphenyl)amino)-1,3-diphenylprop-2-en-1-one (5 mmol) was taken in polyphodphoric acid (5 ml) and heated at 140 °C for 5 h. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with water (50 ml). The aqueous layer was extracted with ethyl acetate (3 X 20 ml), the combined ethyl acetatelayer was washed with 0.1 N NaOH (2 X 25 ml), followed by brine solution (25 ml). The organic layer was then dried over anhydrous sodium sulfate nd concentrated under reduced pressure to afford the crude product 6,7-dimethoxy-2,4-diphenylquinoline which was purified by coloumn
over silica gel (60–120 mesh) using a hexane:ethyl acetate mixture (9.5:0.5) as The pure title compound was crystallized in an ethyl acetate-hexane mixture to obtain pale yellow single crystals.All hydrogen atoms were located geometrically with (C—H = 0.93–0.96) Å and allowed to ride on their parent atoms with Uiso(H) = 1.2Ueq(aromatic C) or 1.5Uiso(methyl C).
Quinolines exhibit physico-chemical activities which are useful in the field of pharmaceuticals and agrochemicals. Their derivatives are also present in a wide variety of natural products involved in several biological activities (Michael, 2006). The
of the title compound is presented here as a part of our on-going structural studies on quinoline derivatives. The consists of two symmetry-independent title molecules (A and B) (Fig. 1). The dihedral angle between phenyl ring [C1/C2/C3/C4/C5/C6 (A/B)] and quinoline moiety are 60.44 (7)° (A) and 56.04 (8)° (B). The dihedral angle between phenyl rings bridged by quinoline moiety are 76.25 (8)° (A) and 70.39 (9) ° (B). Also, the quinoline moiety makes a dihedral angle of 29.14 (8)° (A) and 24.64 (8)° (B) with phenyl ring C21/C22/C23/C24/C25/C26 (A/B). The overall geometry of the title compound is similar to the earlier reported structure of 2-(4-chlorophenyl)-6-methyl-4-m-tolyl quinoline (Prabhuswamy et al., 2012).The molecules are connected by intermolecular hydrogen bonds C6A–H6A···O19B (Fig. 2). The π···π interactions between Cg(6) and Cg(6)i with a distance of 3.7370 (8) Å [i: 1 - x, 2 - y, -z]. The C—H···π interactions, C18B–H18F···Cg(9) [x, 1 + y, z] and C20B–H20D···Cg(6) [2 - x, 2 - y, z], Table 2, link molecules to stabilize the three-dimensional crystal structure.
is further stabilized byQuinolines exhibit physico-chemical activities which are useful in the field of pharmaceuticals and agrochemicals. Their derivatives are also present in a wide variety of natural products involved in several biological activities (Michael, 2006). The
of the title compound is presented here as a part of our on-going structural studies on quinoline derivatives. The consists of two symmetry-independent title molecules (A and B) (Fig. 1). The dihedral angle between phenyl ring [C1/C2/C3/C4/C5/C6 (A/B)] and quinoline moiety are 60.44 (7)° (A) and 56.04 (8)° (B). The dihedral angle between phenyl rings bridged by quinoline moiety are 76.25 (8)° (A) and 70.39 (9) ° (B). Also, the quinoline moiety makes a dihedral angle of 29.14 (8)° (A) and 24.64 (8)° (B) with phenyl ring C21/C22/C23/C24/C25/C26 (A/B). The overall geometry of the title compound is similar to the earlier reported structure of 2-(4-chlorophenyl)-6-methyl-4-m-tolyl quinoline (Prabhuswamy et al., 2012).The molecules are connected by intermolecular hydrogen bonds C6A–H6A···O19B (Fig. 2). The π···π interactions between Cg(6) and Cg(6)i with a distance of 3.7370 (8) Å [i: 1 - x, 2 - y, -z]. The C—H···π interactions, C18B–H18F···Cg(9) [x, 1 + y, z] and C20B–H20D···Cg(6) [2 - x, 2 - y, z], Table 2, link molecules to stabilize the three-dimensional crystal structure.
is further stabilized byFor general background and the biological and pharmacological properties of quinoline derivatives, see: Michael (2006). For related a structure, see: Prabhuswamy et al. (2012).
The enaminone (Z)-3((3,4-dimethoxyphenyl)amino)-1,3-diphenylprop-2-en-1-one (5 mmol) was taken in polyphodphoric acid (5 ml) and heated at 140 °C for 5 h. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with water (50 ml). The aqueous layer was extracted with ethyl acetate (3 X 20 ml), the combined ethyl acetatelayer was washed with 0.1 N NaOH (2 X 25 ml), followed by brine solution (25 ml). The organic layer was then dried over anhydrous sodium sulfate nd concentrated under reduced pressure to afford the crude product 6,7-dimethoxy-2,4-diphenylquinoline which was purified by coloumn
over silica gel (60–120 mesh) using a hexane:ethyl acetate mixture (9.5:0.5) as The pure title compound was crystallized in an ethyl acetate-hexane mixture to obtain pale yellow single crystals. detailsAll hydrogen atoms were located geometrically with (C—H = 0.93–0.96) Å and allowed to ride on their parent atoms with Uiso(H) = 1.2Ueq(aromatic C) or 1.5Uiso(methyl C).
Data collection: APEX2 (Bruker, 2013); cell
SAINT-Plus (Bruker, 2013); data reduction: SAINT-Plus (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., 2006); software used to prepare material for publication: PLATON (Spek, 2009).Fig. 1. ORTEP view of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at 50% probability level. | |
Fig. 2. Packing of molecules of the title compound, viewed along the crystallographic b axis. Dotted lines represent C—H···O hydrogen bond interaction. |
C23H19NO2 | Z = 4 |
Mr = 341.39 | F(000) = 720 |
Triclinic, P1 | Dx = 1.253 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54178 Å |
a = 8.7092 (3) Å | Cell parameters from 5877 reflections |
b = 10.5639 (3) Å | θ = 2.2–64.6° |
c = 20.3400 (7) Å | µ = 0.63 mm−1 |
α = 85.678 (1)° | T = 296 K |
β = 79.397 (1)° | Block, yellow |
γ = 80.134 (1)° | 0.23 × 0.21 × 0.14 mm |
V = 1810.33 (10) Å3 |
Bruker X8 Proteum diffractometer | 5877 independent reflections |
Radiation source: Bruker MicroStar microfocus rotating anode | 5181 reflections with I > 2σ(I) |
Helios multilayer optics monochromator | Rint = 0.041 |
Detector resolution: 10.7 pixels mm-1 | θmax = 64.6°, θmin = 2.2° |
φ and ω scans | h = −10→9 |
Absorption correction: multi-scan (SAINT-Plus; Bruker, 2013) | k = −12→11 |
Tmin = 0.868, Tmax = 0.917 | l = −23→23 |
21904 measured reflections |
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)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0647P)2 + 0.2622P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
5877 reflections | Δρmax = 0.13 e Å−3 |
474 parameters | Δρmin = −0.15 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: 0.0037 (4) |
C23H19NO2 | γ = 80.134 (1)° |
Mr = 341.39 | V = 1810.33 (10) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.7092 (3) Å | Cu Kα radiation |
b = 10.5639 (3) Å | µ = 0.63 mm−1 |
c = 20.3400 (7) Å | T = 296 K |
α = 85.678 (1)° | 0.23 × 0.21 × 0.14 mm |
β = 79.397 (1)° |
Bruker X8 Proteum diffractometer | 5877 independent reflections |
Absorption correction: multi-scan (SAINT-Plus; Bruker, 2013) | 5181 reflections with I > 2σ(I) |
Tmin = 0.868, Tmax = 0.917 | Rint = 0.041 |
21904 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.13 e Å−3 |
5877 reflections | Δρmin = −0.15 e Å−3 |
474 parameters |
Experimental. 1H NMR (CDCl3, 300 MHz): 8.30 (d, J=8.0 Hz, 2H, Ar—H); 7.79 (d, J=8. 0 Hz, 2H, Ar—H); 7.41–7.54 (m, 7H, Ar—H); 7.26 (s, 1H, Ar—H); 7.10 (s,1H, Ar—H); 3.91 (s, 3H, OMe); 3.88 (s, 3H, OMe). M. P. 122–124 °C (uncorrected) |
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 e.s.d.'s 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 > σ(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. |
x | y | z | Uiso*/Ueq | ||
O17A | −0.05130 (13) | 0.68563 (10) | 0.59999 (5) | 0.0604 (3) | |
O19A | 0.05651 (14) | 0.49729 (10) | 0.67519 (5) | 0.0620 (4) | |
N10A | 0.42927 (14) | 0.31063 (10) | 0.49004 (5) | 0.0452 (4) | |
C1A | 0.27076 (19) | 0.86258 (16) | 0.27831 (9) | 0.0637 (6) | |
C2A | 0.3218 (2) | 0.87201 (15) | 0.33749 (9) | 0.0650 (6) | |
C3A | 0.3444 (2) | 0.76504 (14) | 0.38049 (8) | 0.0566 (5) | |
C4A | 0.31857 (16) | 0.64666 (13) | 0.36342 (6) | 0.0447 (4) | |
C5A | 0.26951 (18) | 0.63793 (15) | 0.30320 (7) | 0.0544 (5) | |
C6A | 0.2447 (2) | 0.74626 (17) | 0.26104 (8) | 0.0629 (6) | |
C7A | 0.35107 (16) | 0.52976 (12) | 0.40763 (6) | 0.0432 (4) | |
C8A | 0.26898 (16) | 0.52108 (12) | 0.47472 (6) | 0.0418 (4) | |
C9A | 0.31638 (16) | 0.40926 (12) | 0.51407 (6) | 0.0426 (4) | |
C11A | 0.50062 (16) | 0.31963 (12) | 0.42656 (6) | 0.0433 (4) | |
C12A | 0.46396 (17) | 0.42894 (12) | 0.38462 (6) | 0.0450 (4) | |
C13A | 0.14306 (17) | 0.61463 (13) | 0.50322 (7) | 0.0463 (4) | |
C14A | 0.07132 (17) | 0.60191 (13) | 0.56843 (7) | 0.0471 (4) | |
C15A | 0.12742 (17) | 0.49384 (14) | 0.60936 (7) | 0.0482 (4) | |
C16A | 0.24375 (17) | 0.39985 (13) | 0.58243 (7) | 0.0472 (4) | |
C18A | −0.1033 (2) | 0.79914 (17) | 0.56278 (10) | 0.0718 (6) | |
C20A | 0.1173 (3) | 0.39846 (19) | 0.71948 (8) | 0.0763 (7) | |
C21A | 0.62097 (17) | 0.20846 (13) | 0.40190 (7) | 0.0465 (4) | |
C22A | 0.6062 (2) | 0.08659 (15) | 0.42997 (9) | 0.0683 (6) | |
C23A | 0.7163 (3) | −0.01903 (17) | 0.40975 (10) | 0.0810 (7) | |
C24A | 0.8455 (2) | −0.00526 (18) | 0.36108 (10) | 0.0749 (7) | |
C25A | 0.8608 (2) | 0.11475 (17) | 0.33214 (9) | 0.0677 (6) | |
C26A | 0.74891 (19) | 0.22035 (15) | 0.35167 (7) | 0.0547 (5) | |
O17B | 0.76986 (15) | 1.31226 (11) | −0.07274 (6) | 0.0696 (4) | |
O19B | 0.95184 (14) | 1.13055 (11) | −0.13693 (5) | 0.0644 (4) | |
N10B | 0.79196 (15) | 0.81305 (12) | 0.02976 (6) | 0.0525 (4) | |
C1B | 0.2756 (2) | 1.26810 (16) | 0.24162 (8) | 0.0623 (5) | |
C2B | 0.2546 (2) | 1.26622 (18) | 0.17618 (9) | 0.0685 (6) | |
C3B | 0.35796 (19) | 1.18455 (17) | 0.13196 (8) | 0.0610 (5) | |
C4B | 0.48281 (17) | 1.10097 (14) | 0.15279 (7) | 0.0485 (4) | |
C5B | 0.50382 (18) | 1.10581 (14) | 0.21888 (7) | 0.0518 (5) | |
C6B | 0.4010 (2) | 1.18922 (15) | 0.26210 (7) | 0.0575 (5) | |
C7B | 0.58853 (18) | 1.00442 (14) | 0.10822 (7) | 0.0502 (5) | |
C8B | 0.67728 (17) | 1.03974 (14) | 0.04528 (7) | 0.0481 (4) | |
C9B | 0.77830 (17) | 0.93921 (14) | 0.00888 (7) | 0.0489 (4) | |
C11B | 0.70799 (18) | 0.78223 (14) | 0.08849 (7) | 0.0521 (5) | |
C12B | 0.60666 (19) | 0.87656 (15) | 0.12840 (7) | 0.0554 (5) | |
C13B | 0.67477 (18) | 1.16778 (15) | 0.01843 (7) | 0.0521 (5) | |
C14B | 0.76529 (18) | 1.19406 (14) | −0.04178 (7) | 0.0528 (5) | |
C15B | 0.86679 (18) | 1.09210 (15) | −0.07799 (6) | 0.0511 (5) | |
C16B | 0.87288 (18) | 0.96897 (15) | −0.05314 (7) | 0.0513 (5) | |
C18B | 0.6658 (3) | 1.41683 (17) | −0.04165 (10) | 0.0771 (7) | |
C20B | 1.0476 (2) | 1.03192 (19) | −0.17638 (8) | 0.0703 (6) | |
C21B | 0.72866 (19) | 0.64325 (15) | 0.10957 (7) | 0.0535 (5) | |
C22B | 0.8667 (2) | 0.56210 (16) | 0.08426 (8) | 0.0636 (6) | |
C23B | 0.8868 (3) | 0.43197 (18) | 0.10154 (10) | 0.0754 (7) | |
C24B | 0.7698 (3) | 0.38066 (19) | 0.14503 (10) | 0.0789 (7) | |
C25B | 0.6340 (3) | 0.45959 (19) | 0.17076 (10) | 0.0788 (7) | |
C26B | 0.6125 (2) | 0.58966 (17) | 0.15338 (9) | 0.0673 (6) | |
H1A | 0.25400 | 0.93510 | 0.25000 | 0.0760* | |
H2A | 0.34120 | 0.95080 | 0.34880 | 0.0780* | |
H3A | 0.37710 | 0.77260 | 0.42090 | 0.0680* | |
H5A | 0.25310 | 0.55900 | 0.29090 | 0.0650* | |
H6A | 0.21020 | 0.73980 | 0.22100 | 0.0760* | |
H12A | 0.51740 | 0.43250 | 0.34070 | 0.0540* | |
H13A | 0.10840 | 0.68620 | 0.47710 | 0.0560* | |
H16A | 0.27630 | 0.32840 | 0.60910 | 0.0570* | |
H18A | −0.01720 | 0.84660 | 0.54900 | 0.1080* | |
H18B | −0.18870 | 0.85120 | 0.59020 | 0.1080* | |
H18C | −0.13900 | 0.77630 | 0.52400 | 0.1080* | |
H20A | 0.10070 | 0.31670 | 0.70690 | 0.1140* | |
H20B | 0.06370 | 0.41390 | 0.76450 | 0.1140* | |
H20C | 0.22860 | 0.39810 | 0.71690 | 0.1140* | |
H22A | 0.51990 | 0.07600 | 0.46320 | 0.0820* | |
H23A | 0.70330 | −0.10000 | 0.42900 | 0.0970* | |
H24A | 0.92140 | −0.07620 | 0.34790 | 0.0900* | |
H25A | 0.94750 | 0.12490 | 0.29900 | 0.0810* | |
H26A | 0.75970 | 0.30050 | 0.33080 | 0.0660* | |
H1B | 0.20540 | 1.32230 | 0.27140 | 0.0750* | |
H2B | 0.17030 | 1.32030 | 0.16160 | 0.0820* | |
H3B | 0.34350 | 1.18570 | 0.08770 | 0.0730* | |
H5B | 0.58790 | 1.05230 | 0.23400 | 0.0620* | |
H6B | 0.41740 | 1.19170 | 0.30590 | 0.0690* | |
H12B | 0.55070 | 0.85160 | 0.16940 | 0.0660* | |
H13B | 0.61050 | 1.23490 | 0.04220 | 0.0620* | |
H16B | 0.93980 | 0.90330 | −0.07700 | 0.0620* | |
H18D | 0.55880 | 1.40100 | −0.03650 | 0.1160* | |
H18E | 0.67680 | 1.49410 | −0.06890 | 0.1160* | |
H18F | 0.69090 | 1.42650 | 0.00150 | 0.1160* | |
H20D | 1.12500 | 0.98500 | −0.15180 | 0.1060* | |
H20E | 1.10030 | 1.06940 | −0.21690 | 0.1060* | |
H20F | 0.98250 | 0.97450 | −0.18720 | 0.1060* | |
H22B | 0.94680 | 0.59590 | 0.05520 | 0.0760* | |
H23B | 0.97950 | 0.37890 | 0.08380 | 0.0910* | |
H24B | 0.78310 | 0.29320 | 0.15680 | 0.0950* | |
H25B | 0.55510 | 0.42540 | 0.20030 | 0.0950* | |
H26B | 0.51920 | 0.64180 | 0.17120 | 0.0810* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O17A | 0.0577 (6) | 0.0581 (6) | 0.0594 (6) | −0.0022 (5) | 0.0021 (5) | −0.0115 (5) |
O19A | 0.0754 (7) | 0.0645 (7) | 0.0415 (5) | −0.0149 (5) | 0.0056 (5) | −0.0036 (5) |
N10A | 0.0557 (7) | 0.0386 (6) | 0.0404 (6) | −0.0073 (5) | −0.0070 (5) | 0.0002 (4) |
C1A | 0.0562 (9) | 0.0581 (10) | 0.0674 (10) | −0.0009 (7) | −0.0050 (7) | 0.0245 (8) |
C2A | 0.0771 (11) | 0.0421 (8) | 0.0718 (11) | −0.0082 (7) | −0.0086 (9) | 0.0095 (7) |
C3A | 0.0727 (10) | 0.0434 (8) | 0.0538 (8) | −0.0091 (7) | −0.0143 (7) | 0.0038 (6) |
C4A | 0.0474 (7) | 0.0417 (7) | 0.0419 (7) | −0.0046 (6) | −0.0048 (6) | 0.0043 (5) |
C5A | 0.0597 (9) | 0.0545 (8) | 0.0499 (8) | −0.0100 (7) | −0.0139 (7) | 0.0040 (6) |
C6A | 0.0616 (10) | 0.0744 (11) | 0.0506 (8) | −0.0070 (8) | −0.0156 (7) | 0.0165 (7) |
C7A | 0.0515 (8) | 0.0382 (7) | 0.0410 (7) | −0.0103 (6) | −0.0097 (6) | 0.0015 (5) |
C8A | 0.0493 (7) | 0.0375 (7) | 0.0402 (7) | −0.0112 (6) | −0.0086 (6) | 0.0001 (5) |
C9A | 0.0500 (7) | 0.0379 (7) | 0.0406 (7) | −0.0100 (6) | −0.0076 (6) | −0.0011 (5) |
C11A | 0.0506 (8) | 0.0384 (7) | 0.0413 (7) | −0.0088 (6) | −0.0081 (6) | −0.0013 (5) |
C12A | 0.0547 (8) | 0.0417 (7) | 0.0376 (6) | −0.0089 (6) | −0.0055 (6) | 0.0015 (5) |
C13A | 0.0511 (8) | 0.0413 (7) | 0.0468 (7) | −0.0079 (6) | −0.0092 (6) | −0.0008 (6) |
C14A | 0.0477 (7) | 0.0456 (7) | 0.0486 (7) | −0.0104 (6) | −0.0044 (6) | −0.0088 (6) |
C15A | 0.0546 (8) | 0.0507 (8) | 0.0406 (7) | −0.0182 (6) | −0.0011 (6) | −0.0051 (6) |
C16A | 0.0594 (8) | 0.0427 (7) | 0.0400 (7) | −0.0134 (6) | −0.0066 (6) | 0.0020 (5) |
C18A | 0.0694 (11) | 0.0617 (10) | 0.0766 (11) | 0.0099 (8) | −0.0084 (9) | −0.0116 (8) |
C20A | 0.0955 (14) | 0.0883 (13) | 0.0417 (8) | −0.0177 (11) | −0.0042 (8) | 0.0056 (8) |
C21A | 0.0546 (8) | 0.0430 (7) | 0.0423 (7) | −0.0059 (6) | −0.0108 (6) | −0.0028 (5) |
C22A | 0.0830 (12) | 0.0456 (8) | 0.0630 (10) | 0.0028 (8) | 0.0065 (8) | 0.0058 (7) |
C23A | 0.1048 (15) | 0.0467 (9) | 0.0766 (12) | 0.0104 (9) | −0.0001 (11) | 0.0018 (8) |
C24A | 0.0804 (12) | 0.0610 (11) | 0.0758 (11) | 0.0148 (9) | −0.0112 (10) | −0.0211 (9) |
C25A | 0.0626 (10) | 0.0716 (11) | 0.0658 (10) | −0.0066 (8) | 0.0015 (8) | −0.0237 (8) |
C26A | 0.0613 (9) | 0.0506 (8) | 0.0528 (8) | −0.0126 (7) | −0.0052 (7) | −0.0098 (6) |
O17B | 0.0852 (8) | 0.0573 (7) | 0.0588 (6) | −0.0059 (6) | −0.0026 (6) | 0.0086 (5) |
O19B | 0.0722 (7) | 0.0734 (7) | 0.0400 (5) | −0.0069 (6) | 0.0010 (5) | 0.0085 (5) |
N10B | 0.0612 (7) | 0.0534 (7) | 0.0430 (6) | −0.0122 (6) | −0.0058 (5) | −0.0045 (5) |
C1B | 0.0676 (10) | 0.0576 (9) | 0.0588 (9) | −0.0155 (8) | 0.0063 (8) | −0.0137 (7) |
C2B | 0.0567 (10) | 0.0757 (11) | 0.0703 (11) | −0.0029 (8) | −0.0103 (8) | −0.0054 (8) |
C3B | 0.0589 (9) | 0.0794 (11) | 0.0476 (8) | −0.0146 (8) | −0.0115 (7) | −0.0086 (7) |
C4B | 0.0525 (8) | 0.0540 (8) | 0.0411 (7) | −0.0192 (7) | −0.0023 (6) | −0.0062 (6) |
C5B | 0.0585 (9) | 0.0564 (8) | 0.0411 (7) | −0.0144 (7) | −0.0059 (6) | −0.0019 (6) |
C6B | 0.0735 (10) | 0.0595 (9) | 0.0413 (7) | −0.0213 (8) | −0.0021 (7) | −0.0082 (6) |
C7B | 0.0544 (8) | 0.0577 (9) | 0.0408 (7) | −0.0171 (7) | −0.0040 (6) | −0.0086 (6) |
C8B | 0.0535 (8) | 0.0546 (8) | 0.0385 (7) | −0.0145 (6) | −0.0068 (6) | −0.0068 (6) |
C9B | 0.0553 (8) | 0.0548 (8) | 0.0389 (7) | −0.0145 (7) | −0.0078 (6) | −0.0048 (6) |
C11B | 0.0587 (9) | 0.0566 (8) | 0.0432 (7) | −0.0179 (7) | −0.0060 (6) | −0.0040 (6) |
C12B | 0.0649 (9) | 0.0583 (9) | 0.0433 (7) | −0.0207 (7) | 0.0007 (7) | −0.0049 (6) |
C13B | 0.0588 (9) | 0.0538 (8) | 0.0437 (7) | −0.0102 (7) | −0.0060 (6) | −0.0078 (6) |
C14B | 0.0603 (9) | 0.0550 (8) | 0.0439 (7) | −0.0113 (7) | −0.0110 (6) | 0.0023 (6) |
C15B | 0.0543 (8) | 0.0646 (9) | 0.0345 (7) | −0.0120 (7) | −0.0074 (6) | 0.0015 (6) |
C16B | 0.0572 (9) | 0.0587 (9) | 0.0372 (7) | −0.0086 (7) | −0.0052 (6) | −0.0059 (6) |
C18B | 0.0986 (14) | 0.0578 (10) | 0.0701 (11) | −0.0016 (9) | −0.0152 (10) | 0.0032 (8) |
C20B | 0.0663 (10) | 0.0897 (12) | 0.0443 (8) | 0.0012 (9) | 0.0026 (7) | 0.0036 (8) |
C21B | 0.0635 (9) | 0.0556 (8) | 0.0450 (7) | −0.0174 (7) | −0.0118 (7) | −0.0025 (6) |
C22B | 0.0667 (10) | 0.0640 (10) | 0.0600 (9) | −0.0118 (8) | −0.0119 (8) | 0.0023 (7) |
C23B | 0.0835 (13) | 0.0639 (11) | 0.0776 (12) | −0.0013 (9) | −0.0231 (10) | 0.0030 (9) |
C24B | 0.1077 (16) | 0.0585 (10) | 0.0750 (12) | −0.0177 (11) | −0.0284 (11) | 0.0099 (9) |
C25B | 0.0996 (15) | 0.0705 (12) | 0.0712 (11) | −0.0360 (11) | −0.0132 (10) | 0.0125 (9) |
C26B | 0.0750 (11) | 0.0630 (10) | 0.0634 (10) | −0.0205 (9) | −0.0031 (8) | −0.0001 (8) |
O17A—C14A | 1.3581 (18) | C20A—H20C | 0.9600 |
O17A—C18A | 1.421 (2) | C22A—H22A | 0.9300 |
O19A—C15A | 1.3678 (17) | C23A—H23A | 0.9300 |
O19A—C20A | 1.423 (2) | C24A—H24A | 0.9300 |
O17B—C18B | 1.412 (2) | C25A—H25A | 0.9300 |
O17B—C14B | 1.3589 (19) | C26A—H26A | 0.9300 |
O19B—C20B | 1.417 (2) | C1B—C2B | 1.379 (2) |
O19B—C15B | 1.3615 (17) | C1B—C6B | 1.365 (2) |
N10A—C11A | 1.3300 (16) | C2B—C3B | 1.384 (2) |
N10A—C9A | 1.3565 (17) | C3B—C4B | 1.388 (2) |
N10B—C11B | 1.3302 (19) | C4B—C5B | 1.395 (2) |
N10B—C9B | 1.3600 (19) | C4B—C7B | 1.490 (2) |
C1A—C6A | 1.369 (2) | C5B—C6B | 1.381 (2) |
C1A—C2A | 1.374 (3) | C7B—C8B | 1.428 (2) |
C2A—C3A | 1.385 (2) | C7B—C12B | 1.373 (2) |
C3A—C4A | 1.388 (2) | C8B—C9B | 1.417 (2) |
C4A—C5A | 1.3837 (19) | C8B—C13B | 1.418 (2) |
C4A—C7A | 1.4901 (18) | C9B—C16B | 1.420 (2) |
C5A—C6A | 1.388 (2) | C11B—C12B | 1.410 (2) |
C7A—C8A | 1.4235 (17) | C11B—C21B | 1.488 (2) |
C7A—C12A | 1.3664 (19) | C13B—C14B | 1.366 (2) |
C8A—C13A | 1.4129 (19) | C14B—C15B | 1.428 (2) |
C8A—C9A | 1.4207 (18) | C15B—C16B | 1.356 (2) |
C9A—C16A | 1.4214 (19) | C21B—C22B | 1.390 (2) |
C11A—C12A | 1.4101 (18) | C21B—C26B | 1.388 (2) |
C11A—C21A | 1.4842 (19) | C22B—C23B | 1.383 (3) |
C13A—C14A | 1.366 (2) | C23B—C24B | 1.378 (3) |
C14A—C15A | 1.432 (2) | C24B—C25B | 1.367 (3) |
C15A—C16A | 1.358 (2) | C25B—C26B | 1.382 (3) |
C21A—C22A | 1.385 (2) | C1B—H1B | 0.9300 |
C21A—C26A | 1.382 (2) | C2B—H2B | 0.9300 |
C22A—C23A | 1.375 (3) | C3B—H3B | 0.9300 |
C23A—C24A | 1.375 (3) | C5B—H5B | 0.9300 |
C24A—C25A | 1.374 (3) | C6B—H6B | 0.9300 |
C25A—C26A | 1.380 (2) | C12B—H12B | 0.9300 |
C1A—H1A | 0.9300 | C13B—H13B | 0.9300 |
C2A—H2A | 0.9300 | C16B—H16B | 0.9300 |
C3A—H3A | 0.9300 | C18B—H18D | 0.9600 |
C5A—H5A | 0.9300 | C18B—H18E | 0.9600 |
C6A—H6A | 0.9300 | C18B—H18F | 0.9600 |
C12A—H12A | 0.9300 | C20B—H20D | 0.9600 |
C13A—H13A | 0.9300 | C20B—H20E | 0.9600 |
C16A—H16A | 0.9300 | C20B—H20F | 0.9600 |
C18A—H18C | 0.9600 | C22B—H22B | 0.9300 |
C18A—H18B | 0.9600 | C23B—H23B | 0.9300 |
C18A—H18A | 0.9600 | C24B—H24B | 0.9300 |
C20A—H20A | 0.9600 | C25B—H25B | 0.9300 |
C20A—H20B | 0.9600 | C26B—H26B | 0.9300 |
O17A···O19A | 2.5709 (15) | C26B···H12B | 2.7600 |
O17A···C25Ai | 3.404 (2) | C26B···H18Diii | 3.0200 |
O17A···C26Ai | 3.299 (2) | H1A···C5B | 3.0100 |
O17B···O19B | 2.5446 (16) | H1B···O19Aiv | 2.8200 |
O19A···O17A | 2.5709 (15) | H1B···O17Aiv | 2.7100 |
O19A···C5Aii | 3.336 (2) | H2A···H18Biv | 2.5500 |
O19B···C6Aiii | 3.366 (2) | H2A···C6B | 3.0300 |
O19B···O17B | 2.5446 (16) | H2B···C23Bix | 2.9800 |
O17A···H1Biv | 2.7100 | H2B···H23Bix | 2.4700 |
O17B···H22Bv | 2.8900 | H3A···C8A | 3.0300 |
O19A···H5Aii | 2.8100 | H3A···C13A | 3.0400 |
O19A···H26Ai | 2.8600 | H3A···N10Ai | 2.7000 |
O19A···H1Biv | 2.8200 | H3B···C16Biii | 2.9000 |
O19B···H6Aiii | 2.5800 | H3B···C13B | 2.9500 |
N10A···H22A | 2.5400 | H3B···C8B | 3.0500 |
N10A···H23Avi | 2.9400 | H3B···C9Biii | 2.8900 |
N10A···H3Ai | 2.7000 | H3B···H13B | 2.4700 |
N10A···H18Cii | 2.9000 | H3B···N10Biii | 2.8500 |
N10B···H22B | 2.5200 | H5A···O19Aii | 2.8100 |
N10B···H3Biii | 2.8500 | H5A···C12A | 2.9900 |
C1A···C5B | 3.550 (2) | H5B···C12B | 2.9100 |
C3A···C13A | 3.252 (2) | H6A···O19Biii | 2.5800 |
C3B···C13B | 3.244 (2) | H6B···C21Axii | 2.9000 |
C3B···C16Biii | 3.455 (2) | H12A···C26A | 2.7700 |
C5A···O19Aii | 3.336 (2) | H12A···H26A | 2.3100 |
C5A···C20Aii | 3.571 (3) | H12A···C5A | 2.9500 |
C5B···C1A | 3.550 (2) | H12B···C1A | 2.9700 |
C6A···O19Biii | 3.366 (2) | H12B···H26B | 2.2800 |
C9B···C15Bv | 3.580 (2) | H12B···C26B | 2.7600 |
C12A···C16Ai | 3.548 (2) | H12B···C5B | 2.8800 |
C13A···C3A | 3.252 (2) | H13A···C18A | 2.5000 |
C13B···C3B | 3.244 (2) | H13A···C4A | 2.6800 |
C14A···C26Ai | 3.320 (2) | H13A···C3A | 2.7600 |
C15A···C26Ai | 3.563 (2) | H13A···H18A | 2.3100 |
C15B···C9Bv | 3.580 (2) | H13A···H18C | 2.2700 |
C16A···C12Ai | 3.548 (2) | H13B···C18B | 2.5200 |
C16B···C3Biii | 3.455 (2) | H13B···C3B | 2.6900 |
C16B···C16Bv | 3.533 (2) | H13B···C4B | 2.7300 |
C18A···C25Ai | 3.531 (3) | H13B···H18D | 2.3300 |
C18B···C18Bvii | 3.348 (3) | H13B···H18F | 2.3000 |
C20A···C5Aii | 3.571 (3) | H13B···H3B | 2.4700 |
C20B···C25Aviii | 3.530 (2) | H16A···H23Avi | 2.5600 |
C25A···C20Bviii | 3.530 (2) | H16A···H20A | 2.2800 |
C25A···O17Ai | 3.404 (2) | H16A···H20C | 2.3100 |
C25A···C18Ai | 3.531 (3) | H16A···C20A | 2.5000 |
C26A···O17Ai | 3.299 (2) | H16B···H20F | 2.2900 |
C26A···C15Ai | 3.563 (2) | H16B···H20D | 2.2400 |
C26A···C14Ai | 3.320 (2) | H16B···C20B | 2.4800 |
C1A···H12B | 2.9700 | H18A···C25Ai | 3.0700 |
C1A···H24Aix | 3.0900 | H18A···C13A | 2.7400 |
C3A···H13A | 2.7600 | H18A···H13A | 2.3100 |
C3B···H13B | 2.6900 | H18B···H2Aiv | 2.5500 |
C4A···H13A | 2.6800 | H18C···N10Aii | 2.9000 |
C4B···H13B | 2.7300 | H18C···C13A | 2.7200 |
C5A···H12A | 2.9500 | H18C···H13A | 2.2700 |
C5B···H12B | 2.8800 | H18C···C9Aii | 2.9200 |
C5B···H1A | 3.0100 | H18D···C13B | 2.7400 |
C6A···H26B | 2.8400 | H18D···H13B | 2.3300 |
C6B···H2A | 3.0300 | H18D···C18Bvii | 2.8400 |
C7B···H20Dv | 2.8200 | H18D···C26Biii | 3.0200 |
C8A···H3A | 3.0300 | H18F···H13B | 2.3000 |
C8B···H3B | 3.0500 | H18F···C23Bxii | 2.9000 |
C8B···H20Dv | 2.9800 | H18F···C13B | 2.7500 |
C9A···H18Cii | 2.9200 | H18F···C22Bxii | 3.0500 |
C9B···H3Biii | 2.8900 | H20A···C16A | 2.7600 |
C12A···H5A | 2.9900 | H20A···H16A | 2.2800 |
C12A···H26A | 2.7700 | H20C···C16A | 2.7100 |
C12B···H5B | 2.9100 | H20C···H16A | 2.3100 |
C12B···H20Dv | 3.0800 | H20D···C16B | 2.7100 |
C12B···H26B | 2.7500 | H20D···C8Bv | 2.9800 |
C13A···H18A | 2.7400 | H20D···C12Bv | 3.0800 |
C13A···H18C | 2.7200 | H20D···C7Bv | 2.8200 |
C13A···H3A | 3.0400 | H20D···H16B | 2.2400 |
C13B···H18D | 2.7400 | H20E···C25Aviii | 3.0900 |
C13B···H3B | 2.9500 | H20E···C24Aviii | 2.9900 |
C13B···H18F | 2.7500 | H20F···H25Aviii | 2.5100 |
C14A···H26Ai | 3.0600 | H20F···C16B | 2.7200 |
C15A···H26Ai | 2.9600 | H20F···H16B | 2.2900 |
C16A···H20A | 2.7600 | H22A···N10A | 2.5400 |
C16A···H20C | 2.7100 | H22A···C22Avi | 2.8400 |
C16B···H20F | 2.7200 | H22A···C23Avi | 3.0800 |
C16B···H20D | 2.7100 | H22A···H22Avi | 2.1400 |
C16B···H3Biii | 2.9000 | H22B···N10B | 2.5200 |
C18A···H13A | 2.5000 | H22B···O17Bv | 2.8900 |
C18B···H18Dvii | 2.8400 | H23A···N10Avi | 2.9400 |
C18B···H13B | 2.5200 | H23A···H16Avi | 2.5600 |
C20A···H16A | 2.5000 | H23B···H2Bxi | 2.4700 |
C20B···H16B | 2.4800 | H24A···C1Axi | 3.0900 |
C20B···H25Aviii | 3.0900 | H25A···H20Fviii | 2.5100 |
C21A···H6Bx | 2.9000 | H25A···C20Bviii | 3.0900 |
C22A···H22Avi | 2.8400 | H26A···O19Ai | 2.8600 |
C22B···H18Fx | 3.0500 | H26A···C14Ai | 3.0600 |
C23A···H22Avi | 3.0800 | H26A···C15Ai | 2.9600 |
C23B···H2Bxi | 2.9800 | H26A···H12A | 2.3100 |
C23B···H18Fx | 2.9000 | H26A···C12A | 2.7700 |
C24A···H20Eviii | 2.9900 | H26B···C6A | 2.8400 |
C25A···H18Ai | 3.0700 | H26B···C12B | 2.7500 |
C25A···H20Eviii | 3.0900 | H26B···H12B | 2.2800 |
C26A···H12A | 2.7700 | ||
C14A—O17A—C18A | 116.90 (12) | C26A—C25A—H25A | 120.00 |
C15A—O19A—C20A | 116.88 (13) | C21A—C26A—H26A | 120.00 |
C14B—O17B—C18B | 117.15 (13) | C25A—C26A—H26A | 120.00 |
C15B—O19B—C20B | 116.43 (13) | C2B—C1B—C6B | 119.05 (15) |
C9A—N10A—C11A | 118.34 (11) | C1B—C2B—C3B | 120.60 (16) |
C9B—N10B—C11B | 118.14 (13) | C2B—C3B—C4B | 120.85 (15) |
C2A—C1A—C6A | 119.87 (16) | C3B—C4B—C5B | 117.72 (14) |
C1A—C2A—C3A | 120.45 (15) | C3B—C4B—C7B | 122.35 (13) |
C2A—C3A—C4A | 120.13 (15) | C5B—C4B—C7B | 119.88 (13) |
C3A—C4A—C5A | 118.89 (13) | C4B—C5B—C6B | 120.68 (14) |
C3A—C4A—C7A | 120.44 (12) | C1B—C6B—C5B | 121.06 (14) |
C5A—C4A—C7A | 120.59 (12) | C4B—C7B—C8B | 122.49 (13) |
C4A—C5A—C6A | 120.44 (14) | C4B—C7B—C12B | 119.72 (13) |
C1A—C6A—C5A | 120.20 (15) | C8B—C7B—C12B | 117.77 (13) |
C4A—C7A—C8A | 121.38 (11) | C7B—C8B—C9B | 116.93 (13) |
C4A—C7A—C12A | 120.15 (11) | C7B—C8B—C13B | 124.48 (13) |
C8A—C7A—C12A | 118.46 (11) | C9B—C8B—C13B | 118.55 (13) |
C7A—C8A—C9A | 116.90 (12) | N10B—C9B—C8B | 123.93 (13) |
C9A—C8A—C13A | 119.02 (11) | N10B—C9B—C16B | 116.62 (13) |
C7A—C8A—C13A | 124.07 (12) | C8B—C9B—C16B | 119.45 (13) |
N10A—C9A—C8A | 123.41 (11) | N10B—C11B—C12B | 121.56 (13) |
C8A—C9A—C16A | 118.80 (12) | N10B—C11B—C21B | 116.13 (13) |
N10A—C9A—C16A | 117.79 (11) | C12B—C11B—C21B | 122.31 (13) |
N10A—C11A—C21A | 116.59 (11) | C7B—C12B—C11B | 121.65 (13) |
N10A—C11A—C12A | 121.88 (12) | C8B—C13B—C14B | 121.01 (14) |
C12A—C11A—C21A | 121.53 (11) | O17B—C14B—C13B | 125.99 (14) |
C7A—C12A—C11A | 120.95 (11) | O17B—C14B—C15B | 114.04 (13) |
C8A—C13A—C14A | 121.20 (13) | C13B—C14B—C15B | 119.97 (13) |
C13A—C14A—C15A | 119.55 (13) | O19B—C15B—C14B | 114.45 (13) |
O17A—C14A—C13A | 125.51 (13) | O19B—C15B—C16B | 125.29 (14) |
O17A—C14A—C15A | 114.93 (12) | C14B—C15B—C16B | 120.26 (13) |
O19A—C15A—C14A | 114.37 (12) | C9B—C16B—C15B | 120.74 (14) |
O19A—C15A—C16A | 125.30 (13) | C11B—C21B—C22B | 119.95 (14) |
C14A—C15A—C16A | 120.32 (13) | C11B—C21B—C26B | 122.21 (15) |
C9A—C16A—C15A | 120.86 (13) | C22B—C21B—C26B | 117.83 (15) |
C22A—C21A—C26A | 117.74 (14) | C21B—C22B—C23B | 121.05 (17) |
C11A—C21A—C22A | 119.28 (13) | C22B—C23B—C24B | 120.2 (2) |
C11A—C21A—C26A | 122.99 (13) | C23B—C24B—C25B | 119.37 (19) |
C21A—C22A—C23A | 121.45 (17) | C24B—C25B—C26B | 120.8 (2) |
C22A—C23A—C24A | 120.20 (17) | C21B—C26B—C25B | 120.75 (18) |
C23A—C24A—C25A | 119.05 (17) | C2B—C1B—H1B | 121.00 |
C24A—C25A—C26A | 120.71 (16) | C6B—C1B—H1B | 120.00 |
C21A—C26A—C25A | 120.82 (14) | C1B—C2B—H2B | 120.00 |
C2A—C1A—H1A | 120.00 | C3B—C2B—H2B | 120.00 |
C6A—C1A—H1A | 120.00 | C2B—C3B—H3B | 120.00 |
C3A—C2A—H2A | 120.00 | C4B—C3B—H3B | 120.00 |
C1A—C2A—H2A | 120.00 | C4B—C5B—H5B | 120.00 |
C2A—C3A—H3A | 120.00 | C6B—C5B—H5B | 120.00 |
C4A—C3A—H3A | 120.00 | C1B—C6B—H6B | 119.00 |
C4A—C5A—H5A | 120.00 | C5B—C6B—H6B | 120.00 |
C6A—C5A—H5A | 120.00 | C7B—C12B—H12B | 119.00 |
C1A—C6A—H6A | 120.00 | C11B—C12B—H12B | 119.00 |
C5A—C6A—H6A | 120.00 | C8B—C13B—H13B | 119.00 |
C7A—C12A—H12A | 120.00 | C14B—C13B—H13B | 120.00 |
C11A—C12A—H12A | 120.00 | C9B—C16B—H16B | 120.00 |
C8A—C13A—H13A | 119.00 | C15B—C16B—H16B | 120.00 |
C14A—C13A—H13A | 119.00 | O17B—C18B—H18D | 109.00 |
C9A—C16A—H16A | 120.00 | O17B—C18B—H18E | 109.00 |
C15A—C16A—H16A | 120.00 | O17B—C18B—H18F | 110.00 |
H18A—C18A—H18B | 109.00 | H18D—C18B—H18E | 109.00 |
H18A—C18A—H18C | 110.00 | H18D—C18B—H18F | 110.00 |
H18B—C18A—H18C | 109.00 | H18E—C18B—H18F | 109.00 |
O17A—C18A—H18C | 109.00 | O19B—C20B—H20D | 110.00 |
O17A—C18A—H18A | 109.00 | O19B—C20B—H20E | 109.00 |
O17A—C18A—H18B | 109.00 | O19B—C20B—H20F | 110.00 |
O19A—C20A—H20A | 109.00 | H20D—C20B—H20E | 109.00 |
H20A—C20A—H20C | 109.00 | H20D—C20B—H20F | 109.00 |
H20B—C20A—H20C | 109.00 | H20E—C20B—H20F | 109.00 |
O19A—C20A—H20B | 110.00 | C21B—C22B—H22B | 119.00 |
O19A—C20A—H20C | 109.00 | C23B—C22B—H22B | 120.00 |
H20A—C20A—H20B | 109.00 | C22B—C23B—H23B | 120.00 |
C21A—C22A—H22A | 119.00 | C24B—C23B—H23B | 120.00 |
C23A—C22A—H22A | 119.00 | C23B—C24B—H24B | 120.00 |
C22A—C23A—H23A | 120.00 | C25B—C24B—H24B | 120.00 |
C24A—C23A—H23A | 120.00 | C24B—C25B—H25B | 120.00 |
C25A—C24A—H24A | 120.00 | C26B—C25B—H25B | 120.00 |
C23A—C24A—H24A | 120.00 | C21B—C26B—H26B | 120.00 |
C24A—C25A—H25A | 120.00 | C25B—C26B—H26B | 120.00 |
C18A—O17A—C14A—C13A | −3.5 (2) | C26A—C21A—C22A—C23A | 1.3 (3) |
C18A—O17A—C14A—C15A | 175.50 (13) | C11A—C21A—C26A—C25A | 177.63 (15) |
C20A—O19A—C15A—C14A | −174.49 (15) | C22A—C21A—C26A—C25A | −2.4 (2) |
C20A—O19A—C15A—C16A | 4.3 (2) | C11A—C21A—C22A—C23A | −178.70 (17) |
C18B—O17B—C14B—C15B | 176.50 (16) | C21A—C22A—C23A—C24A | 0.6 (3) |
C18B—O17B—C14B—C13B | −3.5 (2) | C22A—C23A—C24A—C25A | −1.4 (3) |
C20B—O19B—C15B—C14B | −176.60 (14) | C23A—C24A—C25A—C26A | 0.3 (3) |
C20B—O19B—C15B—C16B | 3.4 (2) | C24A—C25A—C26A—C21A | 1.6 (3) |
C11A—N10A—C9A—C8A | 0.8 (2) | C6B—C1B—C2B—C3B | 0.7 (3) |
C11A—N10A—C9A—C16A | −178.51 (13) | C2B—C1B—C6B—C5B | −1.7 (3) |
C9A—N10A—C11A—C21A | −178.76 (12) | C1B—C2B—C3B—C4B | 1.4 (3) |
C9A—N10A—C11A—C12A | 1.1 (2) | C2B—C3B—C4B—C5B | −2.4 (2) |
C11B—N10B—C9B—C16B | 178.32 (14) | C2B—C3B—C4B—C7B | 174.95 (16) |
C9B—N10B—C11B—C12B | 0.3 (2) | C3B—C4B—C5B—C6B | 1.5 (2) |
C11B—N10B—C9B—C8B | −1.4 (2) | C7B—C4B—C5B—C6B | −175.99 (14) |
C9B—N10B—C11B—C21B | −179.18 (14) | C3B—C4B—C7B—C8B | 58.1 (2) |
C6A—C1A—C2A—C3A | −1.2 (3) | C3B—C4B—C7B—C12B | −123.98 (17) |
C2A—C1A—C6A—C5A | 0.1 (3) | C5B—C4B—C7B—C8B | −124.63 (16) |
C1A—C2A—C3A—C4A | 1.3 (3) | C5B—C4B—C7B—C12B | 53.3 (2) |
C2A—C3A—C4A—C5A | −0.3 (2) | C4B—C5B—C6B—C1B | 0.6 (2) |
C2A—C3A—C4A—C7A | 176.64 (15) | C4B—C7B—C8B—C9B | 177.54 (14) |
C3A—C4A—C5A—C6A | −0.8 (2) | C4B—C7B—C8B—C13B | −0.2 (2) |
C7A—C4A—C5A—C6A | −177.73 (14) | C12B—C7B—C8B—C9B | −0.5 (2) |
C3A—C4A—C7A—C8A | 61.2 (2) | C12B—C7B—C8B—C13B | −178.20 (15) |
C3A—C4A—C7A—C12A | −117.36 (16) | C4B—C7B—C12B—C11B | −178.65 (15) |
C5A—C4A—C7A—C12A | 59.5 (2) | C8B—C7B—C12B—C11B | −0.6 (2) |
C5A—C4A—C7A—C8A | −121.89 (15) | C7B—C8B—C9B—N10B | 1.5 (2) |
C4A—C5A—C6A—C1A | 0.9 (3) | C7B—C8B—C9B—C16B | −178.21 (14) |
C4A—C7A—C8A—C9A | −175.81 (12) | C13B—C8B—C9B—N10B | 179.40 (14) |
C4A—C7A—C8A—C13A | 5.6 (2) | C13B—C8B—C9B—C16B | −0.3 (2) |
C12A—C7A—C8A—C13A | −175.79 (14) | C7B—C8B—C13B—C14B | 178.89 (15) |
C4A—C7A—C12A—C11A | 177.53 (13) | C9B—C8B—C13B—C14B | 1.2 (2) |
C12A—C7A—C8A—C9A | 2.8 (2) | N10B—C9B—C16B—C15B | 179.84 (14) |
C8A—C7A—C12A—C11A | −1.1 (2) | C8B—C9B—C16B—C15B | −0.4 (2) |
C9A—C8A—C13A—C14A | 2.8 (2) | N10B—C11B—C12B—C7B | 0.7 (2) |
C7A—C8A—C9A—N10A | −2.8 (2) | C21B—C11B—C12B—C7B | −179.86 (15) |
C7A—C8A—C9A—C16A | 176.52 (13) | N10B—C11B—C21B—C22B | 24.1 (2) |
C13A—C8A—C9A—N10A | 175.91 (13) | N10B—C11B—C21B—C26B | −154.66 (16) |
C13A—C8A—C9A—C16A | −4.8 (2) | C12B—C11B—C21B—C22B | −155.30 (16) |
C7A—C8A—C13A—C14A | −178.60 (14) | C12B—C11B—C21B—C26B | 25.9 (2) |
C8A—C9A—C16A—C15A | 2.1 (2) | C8B—C13B—C14B—O17B | 178.65 (15) |
N10A—C9A—C16A—C15A | −178.55 (14) | C8B—C13B—C14B—C15B | −1.3 (2) |
C21A—C11A—C12A—C7A | 178.92 (13) | O17B—C14B—C15B—O19B | 0.6 (2) |
N10A—C11A—C21A—C22A | 29.0 (2) | O17B—C14B—C15B—C16B | −179.42 (14) |
N10A—C11A—C21A—C26A | −150.99 (14) | C13B—C14B—C15B—O19B | −179.47 (14) |
C12A—C11A—C21A—C22A | −150.90 (15) | C13B—C14B—C15B—C16B | 0.5 (2) |
C12A—C11A—C21A—C26A | 29.1 (2) | O19B—C15B—C16B—C9B | −179.68 (14) |
N10A—C11A—C12A—C7A | −1.0 (2) | C14B—C15B—C16B—C9B | 0.3 (2) |
C8A—C13A—C14A—O17A | −179.21 (14) | C11B—C21B—C22B—C23B | −178.09 (17) |
C8A—C13A—C14A—C15A | 1.8 (2) | C26B—C21B—C22B—C23B | 0.8 (3) |
O17A—C14A—C15A—O19A | −4.81 (19) | C11B—C21B—C26B—C25B | 178.51 (17) |
O17A—C14A—C15A—C16A | 176.33 (13) | C22B—C21B—C26B—C25B | −0.3 (3) |
C13A—C14A—C15A—O19A | 174.25 (13) | C21B—C22B—C23B—C24B | −0.7 (3) |
C13A—C14A—C15A—C16A | −4.6 (2) | C22B—C23B—C24B—C25B | 0.1 (3) |
O19A—C15A—C16A—C9A | −176.15 (14) | C23B—C24B—C25B—C26B | 0.4 (3) |
C14A—C15A—C16A—C9A | 2.6 (2) | C24B—C25B—C26B—C21B | −0.3 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+2, −z; (iv) −x, −y+2, −z+1; (v) −x+2, −y+2, −z; (vi) −x+1, −y, −z+1; (vii) −x+1, −y+3, −z; (viii) −x+2, −y+1, −z; (ix) x−1, y+1, z; (x) x, y−1, z; (xi) x+1, y−1, z; (xii) x, y+1, z. |
Cg6 and Cg9 are the centroids of the N10B,C7B–C9B,C11B,C12B and C21B–C26B rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6A—H6A···O19Biii | 0.93 | 2.58 | 3.366 (2) | 142 |
C18B—H18F···Cg9xii | 0.96 | 2.93 | 3.879 (2) | 169 |
C20B—H20D···Cg6v | 0.96 | 2.93 | 3.59 (18) | 127 |
Symmetry codes: (iii) −x+1, −y+2, −z; (v) −x+2, −y+2, −z; (xii) x, y+1, z. |
Cg6 and Cg9 are the centroids of the N10B,C7B–C9B,C11B,C12B and C21B–C26B rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6A—H6A···O19Bi | 0.93 | 2.58 | 3.366 (2) | 142 |
C18B—H18F···Cg9ii | 0.96 | 2.93 | 3.879 (2) | 169 |
C20B—H20D···Cg6iii | 0.96 | 2.93 | 3.593 (183) | 127 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) x, y+1, z; (iii) −x+2, −y+2, −z. |
Acknowledgements
Authors thank the IOE X-ray diffractometer facility, University of Mysore, Mysore for collecting data.
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