organic compounds
p-tolylpiperidin-4-one
of 1-cyclopropanecarbonyl-3-methyl-2,6-di-aDepartment of Chemistry, Annamalai University, Annamalainagar 608 002, Chidambaram, Tamilnadu, India, bDepartment of Physics, SRM University, Ramapuram Campus, Chennai 600 089, India, and cPost Graduate and Research Department of Botany, Pachaiyappa's College, Chennai 600 030, Tamil Nadu, India
*Correspondence e-mail: krishnasamybala56@gmail.com
The title compound, C24H27NO2, crystallizes with two independent molecules (A and B) in the The two molecules have very similar conformations and each exhibits an intramolecular C—H⋯π interaction. The central piperidine rings adopt boat conformations and the p-tolyl rings are inclined to the mean plane of the piperidine ring by 71.21 (11) and 89.86 (12)° in molecule A and by 68.01 (12) and 89.33 (12)° in molecule B. The cyclopropanecarbonyl group is oriented at an angle of 68.5 (2)° with respect to the mean plane of the piperidine ring in molecule A and 66.2 (2)° in molecule B. In the crystal, the A and B molecules are linked by C—H⋯O hydrogen bonds, enclosing R21(6) ring motifs, forming ribbons running along the a-axis direction.
CCDC reference: 922988
1. Related literature
For the biological activity of piperidine derivatives, see: Aridoss et al. (2009); Nalanishi et al. (1974); Michael (2001); Pinder (1992); Rubiralta et al. (1991). For the of the related compound, 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanylpiperidin-1-yl ketone, see: Sun et al. (2006).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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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: 922988
10.1107/S1600536814018546/su2765sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814018546/su2765Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814018546/su2765Isup3.cml
To a well stirred solution of 3-methyl-2,6-di-p-tolylpiperidin-4-one (1 equiv) and triethylamine (1 equiv) in 30 ml of dry benzene, cyclopropanecarbonyl chloride (1 equiv) in 20 ml of benzene was added drop wise over a period of 30 min. Stirring was continued with mild heating using a magnetic stirrer. After the completion of reaction, it was poured into water and extracted with ether in three 50 ml portions. The combined ether extract was then washed well with 3% sodium bicarbonate solution and dried over anhydrous sodium sulfate. Crystal were obtained by slow evaporation of a solution of the title compound in ethanol.
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 two independent molecules 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 b axis, in which hydrogen bonds form R21(6) bifurcated ring motifs forming ribbons running along a axis. For the sake of clarity, H atoms not involved in hydrogen bonds have been omitted. |
C24H27NO2 | Z = 4 |
Mr = 361.47 | F(000) = 776 |
Triclinic, P1 | Dx = 1.165 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.494 (3) Å | Cell parameters from 7267 reflections |
b = 11.464 (2) Å | θ = 2.7–25° |
c = 17.425 (3) Å | µ = 0.07 mm−1 |
α = 80.265 (15)° | T = 293 K |
β = 86.064 (17)° | Block, white crystalline |
γ = 89.877 (18)° | 0.25 × 0.22 × 0.19 mm |
V = 2061.1 (7) Å3 |
Bruker APEXII CCD area-detector diffractometer | 7267 independent reflections |
Radiation source: fine-focus sealed tube | 4028 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω and ϕ scans | θmax = 25.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→12 |
Tmin = 0.982, Tmax = 0.986 | k = −11→13 |
13683 measured reflections | l = −20→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0688P)2] where P = (Fo2 + 2Fc2)/3 |
7276 reflections | (Δ/σ)max = 0.011 |
493 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
C24H27NO2 | γ = 89.877 (18)° |
Mr = 361.47 | V = 2061.1 (7) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.494 (3) Å | Mo Kα radiation |
b = 11.464 (2) Å | µ = 0.07 mm−1 |
c = 17.425 (3) Å | T = 293 K |
α = 80.265 (15)° | 0.25 × 0.22 × 0.19 mm |
β = 86.064 (17)° |
Bruker APEXII CCD area-detector diffractometer | 7267 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4028 reflections with I > 2σ(I) |
Tmin = 0.982, Tmax = 0.986 | Rint = 0.032 |
13683 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 0.95 | Δρmax = 0.16 e Å−3 |
7276 reflections | Δρmin = −0.14 e Å−3 |
493 parameters |
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 | ||
C1A | 0.2419 (2) | 0.2299 (2) | 0.33693 (13) | 0.0591 (6) | |
H1A | 0.2913 | 0.3040 | 0.3274 | 0.071* | |
C1B | 0.7385 (2) | 0.3525 (2) | 0.34051 (14) | 0.0598 (6) | |
H1B | 0.7873 | 0.2822 | 0.3321 | 0.072* | |
C2A | 0.1458 (2) | 0.2385 (2) | 0.40535 (15) | 0.0755 (8) | |
H2A1 | 0.1897 | 0.2236 | 0.4532 | 0.091* | |
H2A2 | 0.1137 | 0.3188 | 0.3996 | 0.091* | |
C2B | 0.6410 (2) | 0.3116 (2) | 0.40856 (15) | 0.0755 (8) | |
H2B1 | 0.6082 | 0.2344 | 0.4035 | 0.091* | |
H2B2 | 0.6840 | 0.3025 | 0.4567 | 0.091* | |
C3A | 0.0349 (3) | 0.1549 (2) | 0.41292 (14) | 0.0699 (8) | |
C3B | 0.5316 (3) | 0.3931 (3) | 0.41428 (15) | 0.0722 (8) | |
C4A | 0.0335 (2) | 0.0760 (2) | 0.35270 (13) | 0.0553 (6) | |
H4A | 0.1021 | 0.0185 | 0.3630 | 0.066* | |
C4B | 0.5318 (2) | 0.5027 (2) | 0.35287 (13) | 0.0563 (6) | |
H4B | 0.6010 | 0.5542 | 0.3628 | 0.068* | |
C5A | 0.06279 (19) | 0.14576 (18) | 0.27003 (12) | 0.0459 (5) | |
H5A | −0.0128 | 0.1929 | 0.2559 | 0.055* | |
C5B | 0.56099 (18) | 0.47286 (19) | 0.27085 (12) | 0.0475 (5) | |
H5B | 0.4848 | 0.4340 | 0.2570 | 0.057* | |
C6A | −0.0910 (2) | 0.0064 (2) | 0.35850 (16) | 0.0757 (8) | |
H6A1 | −0.1070 | −0.0359 | 0.4107 | 0.114* | |
H6A2 | −0.0847 | −0.0487 | 0.3227 | 0.114* | |
H6A3 | −0.1599 | 0.0599 | 0.3458 | 0.114* | |
C6B | 0.4085 (2) | 0.5713 (3) | 0.35773 (16) | 0.0816 (9) | |
H6B1 | 0.3384 | 0.5233 | 0.3482 | 0.122* | |
H6B2 | 0.4142 | 0.6421 | 0.3193 | 0.122* | |
H6B3 | 0.3950 | 0.5919 | 0.4088 | 0.122* | |
C7A | 0.3389 (2) | 0.1305 (2) | 0.34870 (14) | 0.0571 (6) | |
C7B | 0.8357 (2) | 0.4449 (2) | 0.35131 (13) | 0.0555 (6) | |
C8A | 0.4362 (2) | 0.1284 (2) | 0.29136 (15) | 0.0654 (7) | |
H8A | 0.4416 | 0.1877 | 0.2477 | 0.078* | |
C8B | 0.9348 (2) | 0.4739 (2) | 0.29481 (14) | 0.0619 (7) | |
H8B | 0.9410 | 0.4348 | 0.2521 | 0.074* | |
C9A | 0.5255 (2) | 0.0395 (2) | 0.29806 (17) | 0.0743 (8) | |
H9A | 0.5906 | 0.0411 | 0.2589 | 0.089* | |
C9B | 1.0245 (2) | 0.5594 (2) | 0.30002 (16) | 0.0679 (7) | |
H9B | 1.0901 | 0.5764 | 0.2610 | 0.082* | |
C10A | 0.5215 (2) | −0.0512 (2) | 0.36060 (18) | 0.0731 (8) | |
C10B | 1.0187 (2) | 0.6200 (2) | 0.36181 (17) | 0.0679 (7) | |
C11A | 0.4260 (3) | −0.0472 (3) | 0.41769 (17) | 0.0862 (9) | |
H11A | 0.4210 | −0.1066 | 0.4614 | 0.103* | |
C11B | 0.9221 (3) | 0.5888 (3) | 0.41889 (16) | 0.0809 (8) | |
H11B | 0.9166 | 0.6267 | 0.4621 | 0.097* | |
C12A | 0.3370 (3) | 0.0417 (3) | 0.41257 (15) | 0.0783 (8) | |
H12A | 0.2745 | 0.0416 | 0.4531 | 0.094* | |
C12B | 0.8330 (2) | 0.5025 (3) | 0.41386 (15) | 0.0769 (8) | |
H12B | 0.7696 | 0.4833 | 0.4540 | 0.092* | |
C13A | 0.6162 (3) | −0.1515 (3) | 0.3662 (2) | 0.1086 (11) | |
H13A | 0.5824 | −0.2152 | 0.3441 | 0.163* | |
H13B | 0.6309 | −0.1791 | 0.4200 | 0.163* | |
H13C | 0.6952 | −0.1239 | 0.3380 | 0.163* | |
C13B | 1.1129 (2) | 0.7172 (3) | 0.3665 (2) | 0.0964 (10) | |
H13D | 1.0715 | 0.7924 | 0.3563 | 0.145* | |
H13E | 1.1832 | 0.7150 | 0.3285 | 0.145* | |
H13F | 1.1440 | 0.7060 | 0.4178 | 0.145* | |
C14A | 0.1987 (2) | 0.3155 (2) | 0.20440 (14) | 0.0529 (6) | |
C14B | 0.6965 (2) | 0.3324 (2) | 0.20803 (14) | 0.0531 (6) | |
C15A | 0.1157 (2) | 0.3300 (2) | 0.13864 (14) | 0.0601 (6) | |
H15A | 0.0375 | 0.2817 | 0.1455 | 0.072* | |
C15B | 0.6111 (2) | 0.3498 (2) | 0.14333 (13) | 0.0573 (6) | |
H15B | 0.5313 | 0.3920 | 0.1514 | 0.069* | |
C16A | 0.1098 (3) | 0.4497 (2) | 0.09105 (16) | 0.0867 (9) | |
H16A | 0.0288 | 0.4746 | 0.0704 | 0.104* | |
H16B | 0.1598 | 0.5123 | 0.1060 | 0.104* | |
C16B | 0.6711 (3) | 0.3653 (3) | 0.06201 (15) | 0.0875 (9) | |
H16C | 0.6293 | 0.4175 | 0.0218 | 0.105* | |
H16D | 0.7636 | 0.3660 | 0.0553 | 0.105* | |
C17A | 0.1782 (3) | 0.3580 (3) | 0.05831 (16) | 0.0987 (10) | |
H17A | 0.2707 | 0.3633 | 0.0529 | 0.118* | |
H17B | 0.1397 | 0.3256 | 0.0173 | 0.118* | |
C17B | 0.6075 (3) | 0.2534 (2) | 0.09552 (15) | 0.0814 (8) | |
H17C | 0.6608 | 0.1849 | 0.1096 | 0.098* | |
H17D | 0.5264 | 0.2363 | 0.0760 | 0.098* | |
C18A | 0.08307 (19) | 0.06132 (18) | 0.21231 (13) | 0.0464 (5) | |
C18B | 0.58476 (18) | 0.58418 (18) | 0.21128 (13) | 0.0464 (5) | |
C19A | −0.0090 (2) | 0.0473 (2) | 0.16252 (14) | 0.0565 (6) | |
H19A | −0.0820 | 0.0934 | 0.1621 | 0.068* | |
C19B | 0.4943 (2) | 0.6257 (2) | 0.16086 (14) | 0.0593 (6) | |
H19B | 0.4181 | 0.5838 | 0.1626 | 0.071* | |
C20A | 0.0054 (2) | −0.0349 (2) | 0.11287 (14) | 0.0651 (7) | |
H20A | −0.0583 | −0.0424 | 0.0794 | 0.078* | |
C20B | 0.5143 (2) | 0.7287 (2) | 0.10750 (15) | 0.0689 (7) | |
H20B | 0.4511 | 0.7546 | 0.0739 | 0.083* | |
C21A | 0.1108 (3) | −0.1056 (2) | 0.11164 (15) | 0.0662 (7) | |
C21B | 0.6248 (2) | 0.7937 (2) | 0.10268 (17) | 0.0757 (8) | |
C22A | 0.2031 (2) | −0.0902 (2) | 0.16063 (16) | 0.0735 (8) | |
H22A | 0.2764 | −0.1359 | 0.1605 | 0.088* | |
C22B | 0.7141 (2) | 0.7521 (2) | 0.15385 (18) | 0.0873 (9) | |
H22B | 0.7899 | 0.7945 | 0.1527 | 0.105* | |
C23A | 0.1904 (2) | −0.0082 (2) | 0.21062 (14) | 0.0631 (7) | |
H23A | 0.2549 | 0.0000 | 0.2434 | 0.076* | |
C23B | 0.6951 (2) | 0.6490 (2) | 0.20716 (15) | 0.0672 (7) | |
H23B | 0.7582 | 0.6232 | 0.2408 | 0.081* | |
C24A | 0.1234 (3) | −0.1974 (3) | 0.05885 (18) | 0.1032 (11) | |
H24A | 0.0436 | −0.2389 | 0.0607 | 0.155* | |
H24B | 0.1889 | −0.2524 | 0.0760 | 0.155* | |
H24C | 0.1457 | −0.1591 | 0.0063 | 0.155* | |
C24B | 0.6486 (3) | 0.9056 (3) | 0.0430 (2) | 0.1278 (14) | |
H24D | 0.5799 | 0.9162 | 0.0088 | 0.192* | |
H24E | 0.7277 | 0.8988 | 0.0130 | 0.192* | |
H24F | 0.6531 | 0.9724 | 0.0693 | 0.192* | |
N1A | 0.17108 (15) | 0.22916 (15) | 0.26704 (10) | 0.0496 (5) | |
N1B | 0.66769 (15) | 0.38776 (15) | 0.27005 (10) | 0.0493 (5) | |
O1A | −0.0479 (2) | 0.1532 (2) | 0.46437 (12) | 0.1125 (8) | |
O1B | 0.4475 (2) | 0.3708 (2) | 0.46545 (12) | 0.1167 (8) | |
O2A | 0.29081 (15) | 0.38296 (15) | 0.20209 (11) | 0.0766 (5) | |
O2B | 0.78989 (15) | 0.26785 (16) | 0.20523 (10) | 0.0792 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1A | 0.0691 (15) | 0.0556 (15) | 0.0546 (16) | −0.0053 (12) | −0.0155 (12) | −0.0106 (12) |
C1B | 0.0675 (15) | 0.0546 (15) | 0.0560 (16) | 0.0074 (12) | −0.0123 (12) | −0.0021 (12) |
C2A | 0.0923 (19) | 0.080 (2) | 0.0613 (18) | 0.0145 (16) | −0.0129 (15) | −0.0281 (15) |
C2B | 0.0910 (19) | 0.0755 (19) | 0.0538 (17) | −0.0197 (15) | −0.0091 (14) | 0.0088 (14) |
C3A | 0.0815 (18) | 0.0777 (19) | 0.0480 (16) | 0.0174 (15) | 0.0027 (14) | −0.0064 (14) |
C3B | 0.0752 (18) | 0.091 (2) | 0.0496 (17) | −0.0203 (15) | 0.0045 (14) | −0.0141 (15) |
C4A | 0.0569 (14) | 0.0553 (15) | 0.0496 (15) | 0.0052 (11) | 0.0054 (11) | −0.0007 (12) |
C4B | 0.0530 (13) | 0.0669 (16) | 0.0498 (15) | −0.0043 (11) | 0.0039 (11) | −0.0146 (13) |
C5A | 0.0463 (12) | 0.0448 (13) | 0.0457 (13) | −0.0011 (9) | 0.0007 (10) | −0.0065 (11) |
C5B | 0.0420 (12) | 0.0532 (14) | 0.0487 (14) | 0.0027 (10) | −0.0003 (10) | −0.0138 (11) |
C6A | 0.0624 (15) | 0.0814 (19) | 0.0753 (19) | −0.0104 (13) | 0.0108 (14) | 0.0039 (15) |
C6B | 0.0585 (15) | 0.110 (2) | 0.083 (2) | 0.0064 (15) | 0.0099 (14) | −0.0417 (18) |
C7A | 0.0594 (14) | 0.0585 (16) | 0.0539 (16) | −0.0055 (11) | −0.0152 (12) | −0.0061 (13) |
C7B | 0.0583 (14) | 0.0611 (15) | 0.0473 (15) | 0.0093 (11) | −0.0104 (11) | −0.0069 (12) |
C8A | 0.0609 (15) | 0.0619 (17) | 0.0667 (17) | −0.0073 (13) | −0.0027 (13) | 0.0076 (13) |
C8B | 0.0599 (15) | 0.0656 (17) | 0.0630 (17) | 0.0120 (12) | −0.0042 (13) | −0.0188 (13) |
C9A | 0.0542 (15) | 0.0771 (19) | 0.086 (2) | −0.0043 (13) | 0.0022 (14) | 0.0000 (17) |
C9B | 0.0537 (14) | 0.0768 (19) | 0.0741 (19) | 0.0055 (13) | 0.0004 (13) | −0.0171 (15) |
C10A | 0.0649 (16) | 0.0589 (17) | 0.092 (2) | −0.0104 (13) | −0.0176 (15) | 0.0027 (16) |
C10B | 0.0577 (15) | 0.0664 (17) | 0.084 (2) | 0.0142 (13) | −0.0157 (14) | −0.0206 (16) |
C11A | 0.086 (2) | 0.083 (2) | 0.077 (2) | 0.0012 (16) | −0.0144 (17) | 0.0248 (16) |
C11B | 0.0786 (19) | 0.103 (2) | 0.070 (2) | 0.0010 (17) | −0.0097 (16) | −0.0391 (17) |
C12A | 0.0778 (18) | 0.097 (2) | 0.0528 (17) | 0.0059 (16) | −0.0081 (13) | 0.0088 (16) |
C12B | 0.0719 (17) | 0.107 (2) | 0.0532 (17) | −0.0045 (16) | −0.0018 (13) | −0.0202 (16) |
C13A | 0.085 (2) | 0.070 (2) | 0.166 (3) | 0.0032 (16) | −0.020 (2) | 0.001 (2) |
C13B | 0.0794 (19) | 0.082 (2) | 0.136 (3) | 0.0029 (16) | −0.0143 (18) | −0.040 (2) |
C14A | 0.0558 (14) | 0.0444 (14) | 0.0570 (16) | −0.0012 (11) | −0.0006 (12) | −0.0053 (12) |
C14B | 0.0526 (13) | 0.0484 (14) | 0.0578 (16) | −0.0002 (11) | 0.0021 (11) | −0.0100 (12) |
C15A | 0.0652 (15) | 0.0558 (16) | 0.0557 (16) | −0.0081 (11) | −0.0087 (12) | 0.0026 (13) |
C15B | 0.0632 (14) | 0.0586 (15) | 0.0526 (15) | 0.0025 (11) | 0.0003 (12) | −0.0186 (12) |
C16A | 0.111 (2) | 0.0654 (19) | 0.076 (2) | −0.0039 (16) | −0.0194 (17) | 0.0155 (16) |
C16B | 0.100 (2) | 0.103 (2) | 0.0568 (18) | −0.0139 (18) | 0.0126 (16) | −0.0108 (17) |
C17A | 0.110 (2) | 0.123 (3) | 0.060 (2) | −0.006 (2) | 0.0074 (17) | −0.0110 (19) |
C17B | 0.106 (2) | 0.075 (2) | 0.0696 (19) | −0.0024 (16) | −0.0055 (16) | −0.0301 (16) |
C18A | 0.0457 (12) | 0.0433 (13) | 0.0487 (14) | −0.0048 (10) | 0.0020 (10) | −0.0059 (11) |
C18B | 0.0434 (12) | 0.0448 (13) | 0.0523 (14) | 0.0038 (10) | −0.0021 (10) | −0.0124 (11) |
C19A | 0.0549 (13) | 0.0547 (15) | 0.0610 (16) | 0.0002 (11) | −0.0036 (12) | −0.0128 (13) |
C19B | 0.0542 (13) | 0.0618 (16) | 0.0622 (16) | 0.0004 (11) | −0.0092 (12) | −0.0090 (14) |
C20A | 0.0701 (16) | 0.0656 (17) | 0.0629 (17) | −0.0116 (13) | −0.0086 (13) | −0.0184 (14) |
C20B | 0.0656 (16) | 0.0656 (18) | 0.0734 (19) | 0.0127 (13) | −0.0210 (13) | 0.0009 (15) |
C21A | 0.0795 (18) | 0.0570 (16) | 0.0638 (18) | −0.0051 (14) | 0.0076 (14) | −0.0204 (13) |
C21B | 0.0747 (17) | 0.0571 (17) | 0.088 (2) | 0.0014 (14) | −0.0151 (15) | 0.0117 (15) |
C22A | 0.0673 (17) | 0.0725 (19) | 0.086 (2) | 0.0148 (13) | 0.0004 (15) | −0.0308 (16) |
C22B | 0.0638 (16) | 0.0688 (19) | 0.117 (3) | −0.0151 (13) | −0.0227 (16) | 0.0273 (18) |
C23A | 0.0545 (14) | 0.0678 (17) | 0.0697 (18) | 0.0053 (12) | −0.0036 (12) | −0.0196 (14) |
C23B | 0.0530 (14) | 0.0607 (16) | 0.0824 (19) | −0.0025 (12) | −0.0193 (13) | 0.0092 (14) |
C24A | 0.133 (3) | 0.085 (2) | 0.102 (3) | 0.0090 (19) | −0.001 (2) | −0.049 (2) |
C24B | 0.126 (3) | 0.086 (2) | 0.153 (3) | −0.016 (2) | −0.048 (2) | 0.050 (2) |
N1A | 0.0550 (11) | 0.0465 (11) | 0.0467 (12) | −0.0049 (8) | −0.0083 (9) | −0.0045 (9) |
N1B | 0.0522 (11) | 0.0483 (11) | 0.0478 (12) | 0.0059 (8) | −0.0029 (9) | −0.0092 (9) |
O1A | 0.1181 (16) | 0.147 (2) | 0.0728 (14) | 0.0047 (14) | 0.0338 (13) | −0.0354 (14) |
O1B | 0.1148 (16) | 0.150 (2) | 0.0722 (15) | −0.0259 (14) | 0.0368 (13) | 0.0034 (14) |
O2A | 0.0700 (11) | 0.0646 (11) | 0.0909 (14) | −0.0230 (9) | −0.0138 (9) | 0.0031 (10) |
O2B | 0.0688 (11) | 0.0805 (13) | 0.0948 (14) | 0.0267 (10) | −0.0071 (9) | −0.0332 (11) |
C1A—N1A | 1.471 (3) | C13A—H13A | 0.9600 |
C1A—C7A | 1.523 (3) | C13A—H13B | 0.9600 |
C1A—C2A | 1.524 (3) | C13A—H13C | 0.9600 |
C1A—H1A | 0.9800 | C13B—H13D | 0.9600 |
C1B—N1B | 1.476 (3) | C13B—H13E | 0.9600 |
C1B—C7B | 1.515 (3) | C13B—H13F | 0.9600 |
C1B—C2B | 1.523 (3) | C14A—O2A | 1.233 (2) |
C1B—H1B | 0.9800 | C14A—O2A | 1.233 (2) |
C2A—C3A | 1.494 (3) | C14A—N1A | 1.360 (3) |
C2A—H2A1 | 0.9700 | C14A—C15A | 1.473 (3) |
C2A—H2A2 | 0.9700 | C14B—O2B | 1.230 (2) |
C2B—C3B | 1.487 (3) | C14B—N1B | 1.359 (3) |
C2B—H2B1 | 0.9700 | C14B—C15B | 1.475 (3) |
C2B—H2B2 | 0.9700 | C15A—C16A | 1.482 (3) |
C3A—O1A | 1.202 (3) | C15A—C17A | 1.488 (3) |
C3A—C4A | 1.497 (3) | C15A—H15A | 0.9800 |
C3B—O1B | 1.206 (3) | C15B—C16B | 1.493 (3) |
C3B—C4B | 1.506 (4) | C15B—C17B | 1.495 (3) |
C4A—C6A | 1.521 (3) | C15B—H15B | 0.9800 |
C4A—C5A | 1.536 (3) | C16A—C17A | 1.445 (4) |
C4A—H4A | 0.9800 | C16A—H16A | 0.9700 |
C4B—C6B | 1.517 (3) | C16A—H16B | 0.9700 |
C4B—C5B | 1.536 (3) | C16B—C17B | 1.460 (3) |
C4B—H4B | 0.9800 | C16B—H16C | 0.9700 |
C5A—N1A | 1.479 (2) | C16B—H16D | 0.9700 |
C5A—C18A | 1.514 (3) | C17A—H17A | 0.9700 |
C5A—H5A | 0.9800 | C17A—H17B | 0.9700 |
C5B—N1B | 1.484 (2) | C17B—H17C | 0.9700 |
C5B—C18B | 1.512 (3) | C17B—H17D | 0.9700 |
C5B—H5B | 0.9800 | C18A—C19A | 1.370 (3) |
C6A—H6A1 | 0.9600 | C18A—C23A | 1.380 (3) |
C6A—H6A2 | 0.9600 | C18B—C19B | 1.368 (3) |
C6A—H6A3 | 0.9600 | C18B—C23B | 1.368 (3) |
C6B—H6B1 | 0.9600 | C19A—C20A | 1.384 (3) |
C6B—H6B2 | 0.9600 | C19A—H19A | 0.9300 |
C6B—H6B3 | 0.9600 | C19B—C20B | 1.380 (3) |
C7A—C12A | 1.375 (3) | C19B—H19B | 0.9300 |
C7A—C8A | 1.382 (3) | C20A—C21A | 1.371 (3) |
C7B—C12B | 1.366 (3) | C20A—H20A | 0.9300 |
C7B—C8B | 1.382 (3) | C20B—C21B | 1.370 (3) |
C8A—C9A | 1.379 (3) | C20B—H20B | 0.9300 |
C8A—H8A | 0.9300 | C21A—C22A | 1.365 (4) |
C8B—C9B | 1.379 (3) | C21A—C24A | 1.510 (3) |
C8B—H8B | 0.9300 | C21B—C22B | 1.367 (4) |
C9A—C10A | 1.372 (4) | C21B—C24B | 1.518 (4) |
C9A—H9A | 0.9300 | C22A—C23A | 1.386 (3) |
C9B—C10B | 1.374 (3) | C22A—H22A | 0.9300 |
C9B—H9B | 0.9300 | C22B—C23B | 1.380 (3) |
C10A—C11A | 1.369 (3) | C22B—H22B | 0.9300 |
C10A—C13A | 1.513 (4) | C23A—H23A | 0.9300 |
C10B—C11B | 1.374 (3) | C23B—H23B | 0.9300 |
C10B—C13B | 1.507 (3) | C24A—H24A | 0.9600 |
C11A—C12A | 1.376 (3) | C24A—H24B | 0.9600 |
C11A—H11A | 0.9300 | C24A—H24C | 0.9600 |
C11B—C12B | 1.380 (4) | C24B—H24D | 0.9600 |
C11B—H11B | 0.9300 | C24B—H24E | 0.9600 |
C12A—H12A | 0.9300 | C24B—H24F | 0.9600 |
C12B—H12B | 0.9300 | ||
N1A—C1A—C7A | 112.45 (18) | H13A—C13A—H13C | 109.5 |
N1A—C1A—C2A | 108.28 (18) | H13B—C13A—H13C | 109.5 |
C7A—C1A—C2A | 116.9 (2) | C10B—C13B—H13D | 109.5 |
N1A—C1A—H1A | 106.2 | C10B—C13B—H13E | 109.5 |
C7A—C1A—H1A | 106.2 | H13D—C13B—H13E | 109.5 |
C2A—C1A—H1A | 106.2 | C10B—C13B—H13F | 109.5 |
N1B—C1B—C7B | 112.72 (19) | H13D—C13B—H13F | 109.5 |
N1B—C1B—C2B | 107.62 (18) | H13E—C13B—H13F | 109.5 |
C7B—C1B—C2B | 117.1 (2) | O2A—C14A—N1A | 121.2 (2) |
N1B—C1B—H1B | 106.2 | O2A—C14A—N1A | 121.2 (2) |
C7B—C1B—H1B | 106.2 | O2A—C14A—C15A | 119.4 (2) |
C2B—C1B—H1B | 106.2 | O2A—C14A—C15A | 119.4 (2) |
C3A—C2A—C1A | 114.4 (2) | N1A—C14A—C15A | 119.3 (2) |
C3A—C2A—H2A1 | 108.7 | O2B—C14B—N1B | 121.9 (2) |
C1A—C2A—H2A1 | 108.7 | O2B—C14B—C15B | 119.8 (2) |
C3A—C2A—H2A2 | 108.7 | N1B—C14B—C15B | 118.29 (19) |
C1A—C2A—H2A2 | 108.7 | C14A—C15A—C16A | 117.1 (2) |
H2A1—C2A—H2A2 | 107.6 | C14A—C15A—C17A | 117.6 (2) |
C3B—C2B—C1B | 114.3 (2) | C16A—C15A—C17A | 58.24 (17) |
C3B—C2B—H2B1 | 108.7 | C14A—C15A—H15A | 117.0 |
C1B—C2B—H2B1 | 108.7 | C16A—C15A—H15A | 117.0 |
C3B—C2B—H2B2 | 108.7 | C17A—C15A—H15A | 117.0 |
C1B—C2B—H2B2 | 108.7 | C14B—C15B—C16B | 117.8 (2) |
H2B1—C2B—H2B2 | 107.6 | C14B—C15B—C17B | 116.7 (2) |
O1A—C3A—C2A | 121.0 (2) | C16B—C15B—C17B | 58.50 (16) |
O1A—C3A—C4A | 123.0 (3) | C14B—C15B—H15B | 117.0 |
C2A—C3A—C4A | 116.00 (19) | C16B—C15B—H15B | 117.0 |
O1B—C3B—C2B | 120.9 (3) | C17B—C15B—H15B | 117.0 |
O1B—C3B—C4B | 122.6 (3) | C17A—C16A—C15A | 61.10 (18) |
C2B—C3B—C4B | 116.46 (19) | C17A—C16A—H16A | 117.7 |
C3A—C4A—C6A | 112.08 (19) | C15A—C16A—H16A | 117.7 |
C3A—C4A—C5A | 111.48 (18) | C17A—C16A—H16B | 117.7 |
C6A—C4A—C5A | 111.3 (2) | C15A—C16A—H16B | 117.7 |
C3A—C4A—H4A | 107.2 | H16A—C16A—H16B | 114.8 |
C6A—C4A—H4A | 107.2 | C17B—C16B—C15B | 60.81 (16) |
C5A—C4A—H4A | 107.2 | C17B—C16B—H16C | 117.7 |
C3B—C4B—C6B | 112.18 (19) | C15B—C16B—H16C | 117.7 |
C3B—C4B—C5B | 111.23 (19) | C17B—C16B—H16D | 117.7 |
C6B—C4B—C5B | 111.4 (2) | C15B—C16B—H16D | 117.7 |
C3B—C4B—H4B | 107.2 | H16C—C16B—H16D | 114.8 |
C6B—C4B—H4B | 107.2 | C16A—C17A—C15A | 60.66 (17) |
C5B—C4B—H4B | 107.2 | C16A—C17A—H17A | 117.7 |
N1A—C5A—C18A | 112.76 (15) | C15A—C17A—H17A | 117.7 |
N1A—C5A—C4A | 111.62 (18) | C16A—C17A—H17B | 117.7 |
C18A—C5A—C4A | 110.06 (17) | C15A—C17A—H17B | 117.7 |
N1A—C5A—H5A | 107.4 | H17A—C17A—H17B | 114.8 |
C18A—C5A—H5A | 107.4 | C16B—C17B—C15B | 60.69 (16) |
C4A—C5A—H5A | 107.4 | C16B—C17B—H17C | 117.7 |
N1B—C5B—C18B | 112.55 (15) | C15B—C17B—H17C | 117.7 |
N1B—C5B—C4B | 111.12 (17) | C16B—C17B—H17D | 117.7 |
C18B—C5B—C4B | 110.95 (18) | C15B—C17B—H17D | 117.7 |
N1B—C5B—H5B | 107.3 | H17C—C17B—H17D | 114.8 |
C18B—C5B—H5B | 107.3 | C19A—C18A—C23A | 117.8 (2) |
C4B—C5B—H5B | 107.3 | C19A—C18A—C5A | 120.37 (19) |
C4A—C6A—H6A1 | 109.5 | C23A—C18A—C5A | 121.8 (2) |
C4A—C6A—H6A2 | 109.5 | C19B—C18B—C23B | 117.5 (2) |
H6A1—C6A—H6A2 | 109.5 | C19B—C18B—C5B | 120.83 (19) |
C4A—C6A—H6A3 | 109.5 | C23B—C18B—C5B | 121.7 (2) |
H6A1—C6A—H6A3 | 109.5 | C18A—C19A—C20A | 120.7 (2) |
H6A2—C6A—H6A3 | 109.5 | C18A—C19A—H19A | 119.6 |
C4B—C6B—H6B1 | 109.5 | C20A—C19A—H19A | 119.6 |
C4B—C6B—H6B2 | 109.5 | C18B—C19B—C20B | 121.1 (2) |
H6B1—C6B—H6B2 | 109.5 | C18B—C19B—H19B | 119.4 |
C4B—C6B—H6B3 | 109.5 | C20B—C19B—H19B | 119.4 |
H6B1—C6B—H6B3 | 109.5 | C21A—C20A—C19A | 121.9 (2) |
H6B2—C6B—H6B3 | 109.5 | C21A—C20A—H20A | 119.1 |
C12A—C7A—C8A | 117.0 (2) | C19A—C20A—H20A | 119.1 |
C12A—C7A—C1A | 124.8 (2) | C21B—C20B—C19B | 121.8 (2) |
C8A—C7A—C1A | 118.3 (2) | C21B—C20B—H20B | 119.1 |
C12B—C7B—C8B | 116.8 (2) | C19B—C20B—H20B | 119.1 |
C12B—C7B—C1B | 124.4 (2) | C22A—C21A—C20A | 117.2 (2) |
C8B—C7B—C1B | 118.8 (2) | C22A—C21A—C24A | 121.5 (3) |
C9A—C8A—C7A | 120.9 (2) | C20A—C21A—C24A | 121.3 (3) |
C9A—C8A—H8A | 119.5 | C22B—C21B—C20B | 116.7 (2) |
C7A—C8A—H8A | 119.5 | C22B—C21B—C24B | 121.3 (3) |
C9B—C8B—C7B | 121.8 (2) | C20B—C21B—C24B | 122.0 (3) |
C9B—C8B—H8B | 119.1 | C21A—C22A—C23A | 121.7 (2) |
C7B—C8B—H8B | 119.1 | C21A—C22A—H22A | 119.1 |
C10A—C9A—C8A | 122.2 (2) | C23A—C22A—H22A | 119.1 |
C10A—C9A—H9A | 118.9 | C21B—C22B—C23B | 121.9 (2) |
C8A—C9A—H9A | 118.9 | C21B—C22B—H22B | 119.1 |
C10B—C9B—C8B | 121.2 (2) | C23B—C22B—H22B | 119.1 |
C10B—C9B—H9B | 119.4 | C18A—C23A—C22A | 120.7 (2) |
C8B—C9B—H9B | 119.4 | C18A—C23A—H23A | 119.6 |
C11A—C10A—C9A | 116.4 (3) | C22A—C23A—H23A | 119.6 |
C11A—C10A—C13A | 121.4 (3) | C18B—C23B—C22B | 121.1 (2) |
C9A—C10A—C13A | 122.1 (3) | C18B—C23B—H23B | 119.5 |
C11B—C10B—C9B | 116.9 (2) | C22B—C23B—H23B | 119.5 |
C11B—C10B—C13B | 121.4 (3) | C21A—C24A—H24A | 109.5 |
C9B—C10B—C13B | 121.7 (2) | C21A—C24A—H24B | 109.5 |
C10A—C11A—C12A | 122.2 (3) | H24A—C24A—H24B | 109.5 |
C10A—C11A—H11A | 118.9 | C21A—C24A—H24C | 109.5 |
C12A—C11A—H11A | 118.9 | H24A—C24A—H24C | 109.5 |
C10B—C11B—C12B | 121.8 (3) | H24B—C24A—H24C | 109.5 |
C10B—C11B—H11B | 119.1 | C21B—C24B—H24D | 109.5 |
C12B—C11B—H11B | 119.1 | C21B—C24B—H24E | 109.5 |
C7A—C12A—C11A | 121.2 (2) | H24D—C24B—H24E | 109.5 |
C7A—C12A—H12A | 119.4 | C21B—C24B—H24F | 109.5 |
C11A—C12A—H12A | 119.4 | H24D—C24B—H24F | 109.5 |
C7B—C12B—C11B | 121.5 (2) | H24E—C24B—H24F | 109.5 |
C7B—C12B—H12B | 119.2 | C14A—N1A—C1A | 117.82 (18) |
C11B—C12B—H12B | 119.2 | C14A—N1A—C5A | 121.97 (19) |
C10A—C13A—H13A | 109.5 | C1A—N1A—C5A | 119.75 (17) |
C10A—C13A—H13B | 109.5 | C14B—N1B—C1B | 117.74 (18) |
H13A—C13A—H13B | 109.5 | C14B—N1B—C5B | 121.91 (19) |
C10A—C13A—H13C | 109.5 | C1B—N1B—C5B | 120.12 (16) |
N1A—C1A—C2A—C3A | 47.4 (3) | O2B—C14B—C15B—C17B | 25.2 (3) |
C7A—C1A—C2A—C3A | −80.8 (3) | N1B—C14B—C15B—C17B | −153.8 (2) |
N1B—C1B—C2B—C3B | −47.6 (3) | C14A—C15A—C16A—C17A | 107.2 (2) |
C7B—C1B—C2B—C3B | 80.6 (3) | C14B—C15B—C16B—C17B | 105.9 (3) |
C1A—C2A—C3A—O1A | −179.8 (2) | C14A—C15A—C17A—C16A | −106.3 (3) |
C1A—C2A—C3A—C4A | −0.4 (3) | C14B—C15B—C17B—C16B | −107.6 (2) |
C1B—C2B—C3B—O1B | 179.8 (2) | N1A—C5A—C18A—C19A | −129.1 (2) |
C1B—C2B—C3B—C4B | 0.3 (3) | C4A—C5A—C18A—C19A | 105.6 (2) |
O1A—C3A—C4A—C6A | 7.1 (4) | N1A—C5A—C18A—C23A | 54.4 (3) |
C2A—C3A—C4A—C6A | −172.2 (2) | C4A—C5A—C18A—C23A | −70.9 (2) |
O1A—C3A—C4A—C5A | 132.6 (3) | N1B—C5B—C18B—C19B | 130.0 (2) |
C2A—C3A—C4A—C5A | −46.7 (3) | C4B—C5B—C18B—C19B | −104.7 (2) |
O1B—C3B—C4B—C6B | −6.8 (4) | N1B—C5B—C18B—C23B | −52.0 (3) |
C2B—C3B—C4B—C6B | 172.7 (2) | C4B—C5B—C18B—C23B | 73.2 (2) |
O1B—C3B—C4B—C5B | −132.4 (3) | C23A—C18A—C19A—C20A | 0.6 (3) |
C2B—C3B—C4B—C5B | 47.1 (3) | C5A—C18A—C19A—C20A | −176.07 (19) |
C3A—C4A—C5A—N1A | 44.4 (2) | C23B—C18B—C19B—C20B | 0.5 (3) |
C6A—C4A—C5A—N1A | 170.28 (17) | C5B—C18B—C19B—C20B | 178.6 (2) |
C3A—C4A—C5A—C18A | 170.35 (18) | C18A—C19A—C20A—C21A | 0.4 (4) |
C6A—C4A—C5A—C18A | −63.7 (2) | C18B—C19B—C20B—C21B | −0.1 (4) |
C3B—C4B—C5B—N1B | −43.7 (2) | C19A—C20A—C21A—C22A | −1.2 (4) |
C6B—C4B—C5B—N1B | −169.65 (18) | C19A—C20A—C21A—C24A | 178.2 (2) |
C3B—C4B—C5B—C18B | −169.69 (18) | C19B—C20B—C21B—C22B | −0.5 (4) |
C6B—C4B—C5B—C18B | 64.3 (2) | C19B—C20B—C21B—C24B | 178.6 (3) |
N1A—C1A—C7A—C12A | −118.7 (3) | C20A—C21A—C22A—C23A | 1.1 (4) |
C2A—C1A—C7A—C12A | 7.4 (4) | C24A—C21A—C22A—C23A | −178.3 (2) |
N1A—C1A—C7A—C8A | 61.2 (3) | C20B—C21B—C22B—C23B | 0.8 (5) |
C2A—C1A—C7A—C8A | −172.7 (2) | C24B—C21B—C22B—C23B | −178.4 (3) |
N1B—C1B—C7B—C12B | 118.2 (3) | C19A—C18A—C23A—C22A | −0.7 (3) |
C2B—C1B—C7B—C12B | −7.5 (3) | C5A—C18A—C23A—C22A | 175.9 (2) |
N1B—C1B—C7B—C8B | −61.9 (3) | C21A—C22A—C23A—C18A | −0.1 (4) |
C2B—C1B—C7B—C8B | 172.4 (2) | C19B—C18B—C23B—C22B | −0.2 (4) |
C12A—C7A—C8A—C9A | 1.1 (4) | C5B—C18B—C23B—C22B | −178.3 (2) |
C1A—C7A—C8A—C9A | −178.8 (2) | C21B—C22B—C23B—C18B | −0.4 (4) |
C12B—C7B—C8B—C9B | −1.8 (4) | O2A—C14A—N1A—C1A | 9.3 (3) |
C1B—C7B—C8B—C9B | 178.3 (2) | O2A—C14A—N1A—C1A | 9.3 (3) |
C7A—C8A—C9A—C10A | 0.9 (4) | C15A—C14A—N1A—C1A | −169.75 (18) |
C7B—C8B—C9B—C10B | −0.3 (4) | O2A—C14A—N1A—C5A | −178.56 (18) |
C8A—C9A—C10A—C11A | −1.9 (4) | O2A—C14A—N1A—C5A | −178.56 (18) |
C8A—C9A—C10A—C13A | 177.3 (3) | C15A—C14A—N1A—C5A | 2.4 (3) |
C8B—C9B—C10B—C11B | 2.0 (4) | C7A—C1A—N1A—C14A | −107.7 (2) |
C8B—C9B—C10B—C13B | −177.4 (2) | C2A—C1A—N1A—C14A | 121.7 (2) |
C9A—C10A—C11A—C12A | 1.0 (4) | C7A—C1A—N1A—C5A | 80.0 (2) |
C13A—C10A—C11A—C12A | −178.2 (3) | C2A—C1A—N1A—C5A | −50.7 (3) |
C9B—C10B—C11B—C12B | −1.5 (4) | C18A—C5A—N1A—C14A | 68.3 (2) |
C13B—C10B—C11B—C12B | 177.9 (3) | C4A—C5A—N1A—C14A | −167.24 (17) |
C8A—C7A—C12A—C11A | −2.0 (4) | C18A—C5A—N1A—C1A | −119.7 (2) |
C1A—C7A—C12A—C11A | 177.9 (2) | C4A—C5A—N1A—C1A | 4.8 (2) |
C10A—C11A—C12A—C7A | 1.0 (5) | O2B—C14B—N1B—C1B | −10.3 (3) |
C8B—C7B—C12B—C11B | 2.3 (4) | C15B—C14B—N1B—C1B | 168.65 (19) |
C1B—C7B—C12B—C11B | −177.8 (2) | O2B—C14B—N1B—C5B | 175.21 (19) |
C10B—C11B—C12B—C7B | −0.7 (4) | C15B—C14B—N1B—C5B | −5.8 (3) |
O2A—C14A—C15A—C16A | −26.0 (3) | C7B—C1B—N1B—C14B | 106.7 (2) |
O2A—C14A—C15A—C16A | −26.0 (3) | C2B—C1B—N1B—C14B | −122.6 (2) |
N1A—C14A—C15A—C16A | 153.0 (2) | C7B—C1B—N1B—C5B | −78.8 (2) |
O2A—C14A—C15A—C17A | 40.4 (3) | C2B—C1B—N1B—C5B | 51.9 (3) |
O2A—C14A—C15A—C17A | 40.4 (3) | C18B—C5B—N1B—C14B | −66.5 (2) |
N1A—C14A—C15A—C17A | −140.5 (2) | C4B—C5B—N1B—C14B | 168.39 (19) |
O2B—C14B—C15B—C16B | −41.4 (3) | C18B—C5B—N1B—C1B | 119.2 (2) |
N1B—C14B—C15B—C16B | 139.6 (2) | C4B—C5B—N1B—C1B | −5.9 (3) |
Cg1 and Cg2 are the centroids of the C7A–C12A and C7B–C12B rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C23A—H23A···Cg1 | 0.93 | 2.86 | 3.787 (3) | 173 |
C23B—H23B···Cg2 | 0.93 | 2.85 | 3.777 (3) | 173 |
C5A—H5A···O2Bi | 0.98 | 2.41 | 3.366 (3) | 166 |
C5B—H5B···O2A | 0.98 | 2.42 | 3.381 (3) | 166 |
C19A—H19A···O2Bi | 0.93 | 2.59 | 3.435 (3) | 151 |
Symmetry code: (i) x−1, y, z. |
Cg1 and Cg2 are the centroids of the C7A–C12A and C7B–C12B rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C23A—H23A···Cg1 | 0.93 | 2.86 | 3.787 (3) | 173 |
C23B—H23B···Cg2 | 0.93 | 2.85 | 3.777 (3) | 173 |
C5A—H5A···O2Bi | 0.98 | 2.41 | 3.366 (3) | 166 |
C5B—H5B···O2A | 0.98 | 2.42 | 3.381 (3) | 166 |
C19A—H19A···O2Bi | 0.93 | 2.59 | 3.435 (3) | 151 |
Symmetry code: (i) x−1, y, z. |
Acknowledgements
KK thanks the University Grant Commission for the financial support (major research project, F. No. 42–342/2013) of this research work. The authors are grateful to the UGC Networking Resource Centre, University of Hyderabad, for providing characterization facilities and Dr R. Nagarajan, School of Chemistry, University of Hyderabad, for providing laboratory facilities.
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