supplementary materials


ng5324 scheme

Acta Cryst. (2013). E69, o776    [ doi:10.1107/S1600536813010489 ]

Methyl 9-(4-methoxyphenyl)-19-methyl-3,12-diazapentacyclo[10.7.0.02,10.03,8.013,18]nonadeca-1(19),13(18),14,16-tetraene-10-carboxylate

S. Selvanayagam, B. Sridhar, S. Kathiravan and R. Raghunathan

Abstract top

The title ester, C27H30N2O3, crystallizes with two independent molecules in the asymmetric unit whose geometrical features are similar. In each molecule, the pyrrolidine ring adopts an envelope conformation, with the fused C atom shared with the piperidine ring as the flap, and the piperidine ring adopts a chair conformation. In the crystal, C-H...[pi] interactions link the inversion-related molecules and form a dimeric arrangement in the unit cell.

Comment top

In continuation of our work on the crystal structure analyis of pyrrolidine derivatives, we have undertaken the crystal structure determination of the title compound, and the results are presented here.

The X-ray study confirmed the molecular structure and atomic connectivity for (I), as illustrated in Fig. 1. The asymmetric unit of (I) contains two molecules (Fig. 1); their corresponding bond lengths and bond angles are in good agreement. Fig. 2 shows a superposition of the central pyrrolidine ring of both the molecules using Qmol (Gans & Shalloway, 2001); the r.m.s. deviation is 0.012 Å.

The phenyl ring and the first two five membered rings are planar with the maximum deviation of -0.135 (3) and -0.178 (3) Å for atom C16 in molecules A and B, respectively.

The pyrrolidine ring (third five membered ring) is in an envelope conformation, with puckering parameters (Cremer & Pople, 1975) q2 = 0.464 (3) Å and φ = 73.0 (4) ° for molecule A, and q2 = 0.455 (4) Å and φ = 75.7 (4) ° for molecule B. Atom C14 deviates 0.697 (3) and 0.697 (2) Å from the least-squares plane through the remaining four atoms (C9/N2/C15/C16) of that of ring in molecules A and B, respectively. The piperidine ring adopts a chair conformation. This is confirmed by the puckering parameters q2 = 0.028 (3) Å, q3 = -0.567 (4) Å = QT, δ = 177.2 (4)° for molecule A, and q2 = 0.020 (4) Å, q3 = -0.569 (4) Å = QT, δ = 178.0 (4)° for molecule B.

The molecular structure is influenced by four intramolecular C—H···O close contacts. The crystal packing is stabilized by weak intermolecular C—H···π interactions (Table 1).

Related literature top

For the superposition of molecules using Qmol, see: Gans & Shalloway (2001). For ring-puckering parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of N-alkenyl-3-methyl indole-2-carbaldehyde (1mmol) and pipecolinic acid (1.3mmol) was heated unde Dean-Stark reflux condition for about 12 hours in toluene (10ml) as solvent. The solvent was removed under vacuo. The crude product was subjected to column chromatography using ethyl acetate and hexane as eleuent in 2:1 ratio. Single crystals were grown by slow evaporation from methanol.

Refinement top

H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C—H distances of 0.93-0.98 Å, and Uiso(H) = 1.5Ueq(C) for methyl H and Uiso(H) = 1.2Ueq(C) for all other H atoms.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level
[Figure 2] Fig. 2. Superposition of molecule A (cyan) with the molecule B (pink) in (I).
Methyl 9-(4-methoxyphenyl)-19-methyl-3,12-diazapentacyclo[10.7.0.02,10.03,8.013,18]nonadeca-1(19),13 (18),14,16-tetraene-10-carboxylate top
Crystal data top
C27H30N2O3F(000) = 1840
Mr = 430.53Dx = 1.252 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 22588 reflections
a = 22.672 (3) Åθ = 1.9–27.6°
b = 8.8049 (11) ŵ = 0.08 mm1
c = 24.431 (3) ÅT = 292 K
β = 110.487 (2)°Block, colourless
V = 4568.6 (10) Å30.22 × 0.20 × 0.18 mm
Z = 8
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5762 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.069
Graphite monochromatorθmax = 25.0°, θmin = 1.1°
ω scansh = 2626
42435 measured reflectionsk = 1010
8045 independent reflectionsl = 2929
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.092Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182H-atom parameters constrained
S = 1.18 w = 1/[σ2(Fo2) + (0.0508P)2 + 3.4329P]
where P = (Fo2 + 2Fc2)/3
8045 reflections(Δ/σ)max < 0.001
583 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C27H30N2O3V = 4568.6 (10) Å3
Mr = 430.53Z = 8
Monoclinic, P21/nMo Kα radiation
a = 22.672 (3) ŵ = 0.08 mm1
b = 8.8049 (11) ÅT = 292 K
c = 24.431 (3) Å0.22 × 0.20 × 0.18 mm
β = 110.487 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5762 reflections with I > 2σ(I)
42435 measured reflectionsRint = 0.069
8045 independent reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.092H-atom parameters constrained
wR(F2) = 0.182Δρmax = 0.43 e Å3
S = 1.18Δρmin = 0.16 e Å3
8045 reflectionsAbsolute structure: ?
583 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
xyzUiso*/Ueq
O1A0.93444 (12)0.4156 (3)0.76712 (11)0.0650 (8)
O2A0.97958 (11)0.2081 (3)0.74686 (10)0.0518 (7)
O3A0.98712 (14)0.7518 (3)0.52518 (13)0.0684 (8)
N1A0.77445 (12)0.3472 (3)0.65973 (12)0.0380 (7)
N2A0.85026 (12)0.0283 (3)0.63712 (11)0.0355 (7)
C1A0.71633 (15)0.4049 (4)0.65603 (14)0.0395 (8)
C2A0.69213 (17)0.5525 (4)0.64633 (16)0.0520 (10)
H2A0.71540.63240.63930.062*
C3A0.63208 (18)0.5750 (5)0.64767 (19)0.0645 (12)
H3A0.61480.67200.64170.077*
C4A0.59699 (18)0.4540 (6)0.65787 (19)0.0678 (13)
H4A0.55660.47240.65790.081*
C5A0.62091 (17)0.3086 (5)0.66792 (18)0.0586 (11)
H5A0.59720.23010.67510.070*
C6A0.68210 (15)0.2802 (4)0.66717 (15)0.0417 (9)
C7A0.72152 (15)0.1464 (4)0.67820 (14)0.0399 (8)
C8A0.77736 (15)0.1932 (4)0.67319 (13)0.0345 (8)
C9A0.84286 (14)0.1327 (4)0.68173 (14)0.0347 (8)
H9A0.86180.08830.72080.042*
C10A0.80467 (16)0.0964 (4)0.61825 (16)0.0445 (9)
H10A0.76260.05520.59990.053*
H10B0.80530.15550.65190.053*
C11A0.82090 (17)0.1991 (4)0.57477 (16)0.0477 (9)
H11A0.86050.25070.59460.057*
H11B0.78840.27560.55990.057*
C12A0.82629 (17)0.1066 (4)0.52395 (16)0.0483 (9)
H12A0.78560.06350.50160.058*
H12B0.83910.17240.49830.058*
C13A0.87489 (16)0.0221 (4)0.54669 (15)0.0438 (9)
H13A0.91630.02100.56620.053*
H13B0.87640.08300.51410.053*
C14A0.85678 (15)0.1224 (4)0.58946 (14)0.0355 (8)
H14A0.81700.17470.56890.043*
C15A0.90639 (14)0.2377 (4)0.62553 (14)0.0349 (8)
H15A0.94540.18060.64390.042*
C16A0.88089 (14)0.2804 (4)0.67589 (14)0.0336 (8)
C17A0.83276 (14)0.4144 (4)0.65852 (15)0.0383 (8)
H17A0.84630.49720.68630.046*
H17B0.82760.45210.61980.046*
C18A0.70330 (18)0.0097 (4)0.69300 (17)0.0580 (11)
H18A0.68010.06250.65760.087*
H18B0.67760.00060.71670.087*
H18C0.74060.06600.71400.087*
C19A0.92336 (14)0.3740 (4)0.59520 (14)0.0347 (8)
C20A0.97449 (16)0.4649 (4)0.62738 (16)0.0438 (9)
H20A0.99590.44220.66650.053*
C21A0.99417 (17)0.5878 (4)0.60261 (17)0.0511 (10)
H21A1.02830.64580.62520.061*
C22A0.96325 (18)0.6244 (4)0.54443 (17)0.0471 (9)
C23A0.91267 (18)0.5370 (4)0.51098 (16)0.0487 (10)
H23A0.89180.56010.47180.058*
C24A0.89286 (16)0.4123 (4)0.53676 (15)0.0442 (9)
H24A0.85870.35460.51410.053*
C25A0.9615 (2)0.7860 (5)0.46547 (19)0.0712 (13)
H25A0.96570.69960.44310.107*
H25B0.98350.87090.45710.107*
H25C0.91780.81100.45530.107*
C26A0.93398 (15)0.3123 (4)0.73493 (15)0.0369 (8)
C27A1.03216 (17)0.2245 (5)0.80178 (16)0.0598 (11)
H27A1.05280.31990.80210.090*
H27B1.06150.14310.80570.090*
H27C1.01680.22120.83370.090*
O1B0.92694 (12)0.3911 (3)0.24563 (12)0.0664 (8)
O2B0.96821 (11)0.1798 (3)0.22344 (10)0.0506 (7)
O3B0.93960 (14)0.7123 (3)0.02072 (13)0.0714 (8)
N1B0.76287 (12)0.3170 (3)0.15110 (12)0.0391 (7)
N2B0.83195 (12)0.0008 (3)0.11908 (11)0.0351 (7)
C1B0.70797 (15)0.3754 (4)0.15541 (16)0.0437 (9)
C2B0.68360 (17)0.5233 (4)0.14735 (19)0.0611 (12)
H2B0.70360.60200.13530.073*
C3B0.62788 (19)0.5468 (5)0.1583 (2)0.0754 (14)
H3B0.61060.64390.15390.090*
C4B0.59718 (18)0.4284 (6)0.1758 (2)0.0729 (14)
H4B0.55990.44830.18240.087*
C5B0.62117 (17)0.2829 (5)0.18336 (18)0.0597 (11)
H5B0.60050.20530.19520.072*
C6B0.67779 (15)0.2531 (4)0.17295 (15)0.0443 (9)
C7B0.71620 (16)0.1184 (4)0.17916 (15)0.0416 (8)
C8B0.76781 (15)0.1646 (4)0.16583 (14)0.0357 (8)
C9B0.83080 (14)0.1033 (4)0.16703 (14)0.0349 (8)
H9B0.85350.05690.20510.042*
C10B0.78393 (17)0.1183 (4)0.10156 (16)0.0476 (9)
H10C0.74250.07250.08560.057*
H10D0.78560.17820.13540.057*
C11B0.79522 (19)0.2210 (4)0.05554 (17)0.0545 (10)
H11C0.83410.27700.07320.065*
H11D0.76110.29380.04150.065*
C12B0.79925 (18)0.1278 (4)0.00400 (16)0.0528 (10)
H12C0.80970.19410.02300.063*
H12D0.75870.08160.01670.063*
C13B0.84929 (17)0.0040 (4)0.02554 (15)0.0468 (9)
H13C0.84960.05790.00720.056*
H13D0.89050.05030.04280.056*
C14B0.83553 (15)0.0962 (4)0.07091 (14)0.0349 (8)
H14B0.79570.15030.05270.042*
C15B0.88737 (15)0.2088 (4)0.10429 (13)0.0342 (8)
H15B0.92660.15070.11990.041*
C16B0.86703 (14)0.2515 (3)0.15801 (13)0.0307 (7)
C17B0.81836 (14)0.3840 (4)0.14360 (15)0.0364 (8)
H17C0.83410.46860.17020.044*
H17D0.80890.41940.10380.044*
C18B0.70112 (19)0.0372 (5)0.19660 (18)0.0625 (11)
H18D0.73950.09300.21430.094*
H18E0.67460.09040.16260.094*
H18F0.67970.02710.22400.094*
C19B0.90076 (15)0.3438 (4)0.07165 (14)0.0344 (8)
C20B0.95591 (16)0.4278 (4)0.09698 (16)0.0462 (9)
H20B0.98340.40090.13390.055*
C21B0.97102 (17)0.5518 (4)0.06817 (18)0.0517 (10)
H21B1.00790.60640.08600.062*
C22B0.93026 (19)0.5924 (4)0.01255 (17)0.0487 (10)
C24B0.86112 (16)0.3885 (4)0.01548 (15)0.0430 (9)
H24B0.82420.33460.00280.052*
C23B0.87542 (18)0.5098 (4)0.01331 (17)0.0498 (10)
H23B0.84810.53650.05030.060*
C25B0.9953 (2)0.7948 (5)0.0030 (2)0.0790 (14)
H25D0.99660.84060.03910.119*
H25E0.99690.87260.02400.119*
H25F1.03060.72800.01020.119*
C26B0.92342 (15)0.2853 (4)0.21397 (14)0.0352 (8)
C27B1.02450 (16)0.1965 (5)0.27538 (16)0.0559 (11)
H27D1.04430.29200.27380.084*
H27E1.05320.11530.27690.084*
H27F1.01300.19340.30960.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0552 (17)0.070 (2)0.0578 (17)0.0105 (14)0.0049 (14)0.0295 (16)
O2A0.0458 (15)0.0482 (15)0.0457 (15)0.0134 (12)0.0039 (12)0.0069 (12)
O3A0.081 (2)0.0602 (19)0.070 (2)0.0084 (16)0.0342 (17)0.0040 (16)
N1A0.0334 (15)0.0378 (17)0.0443 (17)0.0014 (13)0.0156 (13)0.0012 (13)
N2A0.0345 (15)0.0307 (15)0.0398 (16)0.0016 (12)0.0110 (13)0.0006 (13)
C1A0.0300 (18)0.049 (2)0.039 (2)0.0025 (17)0.0108 (15)0.0070 (17)
C2A0.041 (2)0.049 (2)0.063 (3)0.0056 (18)0.0156 (19)0.005 (2)
C3A0.047 (2)0.062 (3)0.082 (3)0.018 (2)0.020 (2)0.012 (2)
C4A0.034 (2)0.087 (3)0.082 (3)0.007 (2)0.020 (2)0.020 (3)
C5A0.042 (2)0.071 (3)0.067 (3)0.008 (2)0.025 (2)0.017 (2)
C6A0.0327 (19)0.053 (2)0.039 (2)0.0047 (17)0.0128 (16)0.0109 (17)
C7A0.0371 (19)0.046 (2)0.0371 (19)0.0065 (17)0.0141 (16)0.0050 (16)
C8A0.0361 (19)0.0356 (19)0.0307 (18)0.0001 (15)0.0104 (15)0.0004 (15)
C9A0.0341 (18)0.0356 (19)0.0303 (18)0.0006 (15)0.0060 (14)0.0031 (15)
C10A0.041 (2)0.034 (2)0.056 (2)0.0012 (16)0.0137 (17)0.0034 (17)
C11A0.048 (2)0.032 (2)0.062 (2)0.0013 (17)0.0182 (19)0.0066 (18)
C12A0.052 (2)0.041 (2)0.052 (2)0.0029 (18)0.0190 (19)0.0090 (18)
C13A0.046 (2)0.040 (2)0.048 (2)0.0000 (17)0.0200 (18)0.0058 (17)
C14A0.0315 (17)0.0296 (18)0.043 (2)0.0067 (14)0.0103 (15)0.0036 (15)
C15A0.0276 (17)0.0362 (19)0.0375 (19)0.0048 (14)0.0072 (15)0.0016 (15)
C16A0.0299 (17)0.0343 (19)0.0355 (19)0.0032 (14)0.0103 (15)0.0007 (15)
C17A0.0371 (19)0.0348 (19)0.044 (2)0.0015 (16)0.0158 (16)0.0035 (16)
C18A0.061 (3)0.063 (3)0.059 (3)0.013 (2)0.032 (2)0.002 (2)
C19A0.0334 (18)0.0349 (19)0.040 (2)0.0057 (15)0.0181 (16)0.0003 (15)
C20A0.039 (2)0.048 (2)0.047 (2)0.0026 (17)0.0172 (17)0.0028 (18)
C21A0.045 (2)0.055 (2)0.054 (2)0.0137 (19)0.0173 (19)0.006 (2)
C22A0.054 (2)0.035 (2)0.065 (3)0.0057 (18)0.036 (2)0.0042 (19)
C23A0.059 (2)0.051 (2)0.039 (2)0.011 (2)0.0213 (19)0.0052 (18)
C24A0.044 (2)0.042 (2)0.048 (2)0.0015 (17)0.0167 (18)0.0022 (18)
C25A0.082 (3)0.073 (3)0.068 (3)0.012 (3)0.038 (3)0.006 (2)
C26A0.0383 (19)0.0356 (19)0.038 (2)0.0034 (16)0.0155 (16)0.0038 (17)
C27A0.046 (2)0.065 (3)0.051 (2)0.005 (2)0.0055 (19)0.002 (2)
O1B0.0539 (17)0.0695 (19)0.0602 (18)0.0126 (14)0.0005 (14)0.0304 (16)
O2B0.0404 (14)0.0463 (15)0.0492 (15)0.0112 (12)0.0044 (12)0.0073 (12)
O3B0.081 (2)0.0570 (18)0.085 (2)0.0100 (16)0.0414 (18)0.0069 (16)
N1B0.0349 (16)0.0312 (15)0.0547 (18)0.0003 (13)0.0200 (14)0.0019 (14)
N2B0.0373 (15)0.0289 (15)0.0383 (16)0.0018 (12)0.0123 (13)0.0001 (12)
C1B0.0329 (19)0.046 (2)0.052 (2)0.0016 (17)0.0152 (17)0.0119 (18)
C2B0.042 (2)0.046 (2)0.094 (3)0.0064 (19)0.023 (2)0.006 (2)
C3B0.049 (3)0.056 (3)0.122 (4)0.011 (2)0.032 (3)0.019 (3)
C4B0.037 (2)0.087 (4)0.102 (4)0.003 (2)0.033 (2)0.035 (3)
C5B0.040 (2)0.075 (3)0.072 (3)0.015 (2)0.029 (2)0.023 (2)
C6B0.0335 (19)0.054 (2)0.046 (2)0.0097 (17)0.0136 (17)0.0160 (18)
C7B0.040 (2)0.045 (2)0.042 (2)0.0105 (17)0.0160 (16)0.0053 (17)
C8B0.0401 (19)0.0333 (19)0.0322 (18)0.0020 (15)0.0108 (15)0.0017 (15)
C9B0.0349 (18)0.0367 (19)0.0307 (18)0.0014 (15)0.0084 (14)0.0035 (15)
C10B0.055 (2)0.037 (2)0.051 (2)0.0055 (18)0.0186 (19)0.0014 (18)
C11B0.064 (3)0.035 (2)0.060 (3)0.0080 (19)0.017 (2)0.0101 (19)
C12B0.061 (2)0.044 (2)0.049 (2)0.0004 (19)0.0144 (19)0.0126 (19)
C13B0.051 (2)0.046 (2)0.044 (2)0.0018 (18)0.0187 (18)0.0018 (18)
C14B0.0333 (18)0.0342 (19)0.0361 (19)0.0044 (15)0.0107 (15)0.0039 (15)
C15B0.0299 (17)0.0361 (19)0.0353 (19)0.0037 (15)0.0099 (15)0.0002 (15)
C16B0.0296 (17)0.0290 (17)0.0333 (18)0.0003 (14)0.0107 (14)0.0014 (14)
C17B0.0356 (18)0.0336 (19)0.041 (2)0.0009 (15)0.0147 (16)0.0010 (15)
C18B0.064 (3)0.064 (3)0.069 (3)0.015 (2)0.034 (2)0.002 (2)
C19B0.0336 (18)0.0346 (19)0.0402 (19)0.0016 (15)0.0194 (16)0.0021 (15)
C20B0.042 (2)0.052 (2)0.049 (2)0.0036 (18)0.0223 (18)0.0043 (19)
C21B0.044 (2)0.048 (2)0.073 (3)0.0146 (18)0.033 (2)0.014 (2)
C22B0.067 (3)0.036 (2)0.058 (3)0.0089 (19)0.041 (2)0.0094 (19)
C24B0.043 (2)0.045 (2)0.043 (2)0.0002 (17)0.0173 (17)0.0028 (17)
C23B0.055 (2)0.047 (2)0.050 (2)0.003 (2)0.021 (2)0.0067 (19)
C25B0.085 (3)0.058 (3)0.110 (4)0.012 (3)0.054 (3)0.013 (3)
C26B0.0339 (19)0.036 (2)0.038 (2)0.0015 (16)0.0150 (16)0.0026 (16)
C27B0.039 (2)0.060 (3)0.053 (2)0.0072 (19)0.0042 (18)0.001 (2)
Geometric parameters (Å, º) top
O1A—C26A1.200 (4)O1B—C26B1.195 (4)
O2A—C26A1.336 (4)O2B—C26B1.336 (4)
O2A—C27A1.457 (4)O2B—C27B1.459 (4)
O3A—C22A1.396 (4)O3B—C22B1.393 (4)
O3A—C25A1.401 (5)O3B—C25B1.395 (5)
N1A—C1A1.385 (4)N1B—C8B1.384 (4)
N1A—C8A1.391 (4)N1B—C1B1.384 (4)
N1A—C17A1.458 (4)N1B—C17B1.458 (4)
N2A—C10A1.467 (4)N2B—C10B1.463 (4)
N2A—C14A1.479 (4)N2B—C14B1.471 (4)
N2A—C9A1.479 (4)N2B—C9B1.486 (4)
C1A—C2A1.399 (5)C1B—C2B1.402 (5)
C1A—C6A1.424 (5)C1B—C6B1.420 (5)
C2A—C3A1.387 (5)C2B—C3B1.395 (5)
C2A—H2A0.9300C2B—H2B0.9300
C3A—C4A1.403 (6)C3B—C4B1.400 (6)
C3A—H3A0.9300C3B—H3B0.9300
C4A—C5A1.379 (6)C4B—C5B1.379 (6)
C4A—H4A0.9300C4B—H4B0.9300
C5A—C6A1.416 (5)C5B—C6B1.418 (5)
C5A—H5A0.9300C5B—H5B0.9300
C6A—C7A1.446 (5)C6B—C7B1.447 (5)
C7A—C8A1.377 (4)C7B—C8B1.381 (4)
C7A—C18A1.515 (5)C7B—C18B1.509 (5)
C8A—C9A1.522 (4)C8B—C9B1.518 (4)
C9A—C16A1.594 (4)C9B—C16B1.598 (4)
C9A—H9A0.9800C9B—H9B0.9800
C10A—C11A1.535 (5)C10B—C11B1.532 (5)
C10A—H10A0.9700C10B—H10C0.9700
C10A—H10B0.9700C10B—H10D0.9700
C11A—C12A1.525 (5)C11B—C12B1.532 (5)
C11A—H11A0.9700C11B—H11C0.9700
C11A—H11B0.9700C11B—H11D0.9700
C12A—C13A1.542 (5)C12B—C13B1.528 (5)
C12A—H12A0.9700C12B—H12C0.9700
C12A—H12B0.9700C12B—H12D0.9700
C13A—C14A1.530 (4)C13B—C14B1.532 (4)
C13A—H13A0.9700C13B—H13C0.9700
C13A—H13B0.9700C13B—H13D0.9700
C14A—C15A1.542 (4)C14B—C15B1.536 (4)
C14A—H14A0.9800C14B—H14B0.9800
C15A—C19A1.528 (4)C15B—C19B1.520 (4)
C15A—C16A1.577 (4)C15B—C16B1.581 (4)
C15A—H15A0.9800C15B—H15B0.9800
C16A—C26A1.547 (4)C16B—C26B1.539 (4)
C16A—C17A1.562 (4)C16B—C17B1.559 (4)
C17A—H17A0.9700C17B—H17C0.9700
C17A—H17B0.9700C17B—H17D0.9700
C18A—H18A0.9600C18B—H18D0.9600
C18A—H18B0.9600C18B—H18E0.9600
C18A—H18C0.9600C18B—H18F0.9600
C19A—C24A1.393 (5)C19B—C20B1.397 (4)
C19A—C20A1.402 (5)C19B—C24B1.408 (5)
C20A—C21A1.387 (5)C20B—C21B1.405 (5)
C20A—H20A0.9300C20B—H20B0.9300
C21A—C22A1.385 (5)C21B—C22B1.396 (5)
C21A—H21A0.9300C21B—H21B0.9300
C22A—C23A1.385 (5)C22B—C23B1.387 (5)
C23A—C24A1.415 (5)C24B—C23B1.378 (5)
C23A—H23A0.9300C24B—H24B0.9300
C24A—H24A0.9300C23B—H23B0.9300
C25A—H25A0.9600C25B—H25D0.9600
C25A—H25B0.9600C25B—H25E0.9600
C25A—H25C0.9600C25B—H25F0.9600
C27A—H27A0.9600C27B—H27D0.9600
C27A—H27B0.9600C27B—H27E0.9600
C27A—H27C0.9600C27B—H27F0.9600
C26A—O2A—C27A117.0 (3)C26B—O2B—C27B117.4 (3)
C22A—O3A—C25A117.1 (3)C22B—O3B—C25B116.9 (4)
C1A—N1A—C8A109.7 (3)C8B—N1B—C1B109.5 (3)
C1A—N1A—C17A134.3 (3)C8B—N1B—C17B115.5 (3)
C8A—N1A—C17A115.6 (3)C1B—N1B—C17B134.2 (3)
C10A—N2A—C14A115.2 (3)C10B—N2B—C14B114.8 (3)
C10A—N2A—C9A116.6 (3)C10B—N2B—C9B116.7 (3)
C14A—N2A—C9A107.5 (2)C14B—N2B—C9B107.7 (2)
N1A—C1A—C2A131.3 (3)N1B—C1B—C2B130.9 (3)
N1A—C1A—C6A106.0 (3)N1B—C1B—C6B106.4 (3)
C2A—C1A—C6A122.7 (3)C2B—C1B—C6B122.6 (3)
C3A—C2A—C1A117.3 (4)C3B—C2B—C1B116.7 (4)
C3A—C2A—H2A121.4C3B—C2B—H2B121.6
C1A—C2A—H2A121.4C1B—C2B—H2B121.6
C2A—C3A—C4A121.2 (4)C2B—C3B—C4B121.9 (4)
C2A—C3A—H3A119.4C2B—C3B—H3B119.1
C4A—C3A—H3A119.4C4B—C3B—H3B119.1
C5A—C4A—C3A121.6 (4)C5B—C4B—C3B121.2 (4)
C5A—C4A—H4A119.2C5B—C4B—H4B119.4
C3A—C4A—H4A119.2C3B—C4B—H4B119.4
C4A—C5A—C6A119.2 (4)C4B—C5B—C6B119.2 (4)
C4A—C5A—H5A120.4C4B—C5B—H5B120.4
C6A—C5A—H5A120.4C6B—C5B—H5B120.4
C5A—C6A—C1A117.9 (3)C5B—C6B—C1B118.4 (3)
C5A—C6A—C7A133.3 (3)C5B—C6B—C7B133.0 (4)
C1A—C6A—C7A108.7 (3)C1B—C6B—C7B108.5 (3)
C8A—C7A—C6A105.5 (3)C8B—C7B—C6B105.2 (3)
C8A—C7A—C18A129.0 (3)C8B—C7B—C18B128.9 (3)
C6A—C7A—C18A125.5 (3)C6B—C7B—C18B125.9 (3)
C7A—C8A—N1A110.1 (3)C7B—C8B—N1B110.4 (3)
C7A—C8A—C9A140.0 (3)C7B—C8B—C9B139.5 (3)
N1A—C8A—C9A109.7 (3)N1B—C8B—C9B109.9 (3)
N2A—C9A—C8A118.3 (3)N2B—C9B—C8B118.5 (3)
N2A—C9A—C16A103.7 (2)N2B—C9B—C16B103.6 (2)
C8A—C9A—C16A103.5 (2)C8B—C9B—C16B103.4 (2)
N2A—C9A—H9A110.3N2B—C9B—H9B110.2
C8A—C9A—H9A110.3C8B—C9B—H9B110.2
C16A—C9A—H9A110.3C16B—C9B—H9B110.2
N2A—C10A—C11A110.2 (3)N2B—C10B—C11B109.8 (3)
N2A—C10A—H10A109.6N2B—C10B—H10C109.7
C11A—C10A—H10A109.6C11B—C10B—H10C109.7
N2A—C10A—H10B109.6N2B—C10B—H10D109.7
C11A—C10A—H10B109.6C11B—C10B—H10D109.7
H10A—C10A—H10B108.1H10C—C10B—H10D108.2
C12A—C11A—C10A110.8 (3)C12B—C11B—C10B111.1 (3)
C12A—C11A—H11A109.5C12B—C11B—H11C109.4
C10A—C11A—H11A109.5C10B—C11B—H11C109.4
C12A—C11A—H11B109.5C12B—C11B—H11D109.4
C10A—C11A—H11B109.5C10B—C11B—H11D109.4
H11A—C11A—H11B108.1H11C—C11B—H11D108.0
C11A—C12A—C13A110.5 (3)C13B—C12B—C11B110.5 (3)
C11A—C12A—H12A109.6C13B—C12B—H12C109.6
C13A—C12A—H12A109.6C11B—C12B—H12C109.6
C11A—C12A—H12B109.6C13B—C12B—H12D109.6
C13A—C12A—H12B109.6C11B—C12B—H12D109.6
H12A—C12A—H12B108.1H12C—C12B—H12D108.1
C14A—C13A—C12A110.0 (3)C12B—C13B—C14B110.2 (3)
C14A—C13A—H13A109.7C12B—C13B—H13C109.6
C12A—C13A—H13A109.7C14B—C13B—H13C109.6
C14A—C13A—H13B109.7C12B—C13B—H13D109.6
C12A—C13A—H13B109.7C14B—C13B—H13D109.6
H13A—C13A—H13B108.2H13C—C13B—H13D108.1
N2A—C14A—C13A109.8 (3)N2B—C14B—C13B109.4 (3)
N2A—C14A—C15A100.0 (2)N2B—C14B—C15B101.0 (2)
C13A—C14A—C15A117.0 (3)C13B—C14B—C15B116.4 (3)
N2A—C14A—H14A109.9N2B—C14B—H14B109.9
C13A—C14A—H14A109.9C13B—C14B—H14B109.9
C15A—C14A—H14A109.9C15B—C14B—H14B109.9
C19A—C15A—C14A119.8 (3)C19B—C15B—C14B118.8 (3)
C19A—C15A—C16A114.5 (3)C19B—C15B—C16B114.8 (3)
C14A—C15A—C16A102.1 (2)C14B—C15B—C16B101.7 (2)
C19A—C15A—H15A106.5C19B—C15B—H15B106.9
C14A—C15A—H15A106.5C14B—C15B—H15B106.9
C16A—C15A—H15A106.5C16B—C15B—H15B106.9
C26A—C16A—C17A111.0 (3)C26B—C16B—C17B111.0 (3)
C26A—C16A—C15A113.1 (2)C26B—C16B—C15B113.0 (2)
C17A—C16A—C15A112.3 (3)C17B—C16B—C15B112.3 (3)
C26A—C16A—C9A109.5 (2)C26B—C16B—C9B110.0 (2)
C17A—C16A—C9A107.0 (2)C17B—C16B—C9B106.6 (2)
C15A—C16A—C9A103.5 (2)C15B—C16B—C9B103.5 (2)
N1A—C17A—C16A103.9 (3)N1B—C17B—C16B104.0 (2)
N1A—C17A—H17A111.0N1B—C17B—H17C111.0
C16A—C17A—H17A111.0C16B—C17B—H17C111.0
N1A—C17A—H17B111.0N1B—C17B—H17D111.0
C16A—C17A—H17B111.0C16B—C17B—H17D111.0
H17A—C17A—H17B109.0H17C—C17B—H17D109.0
C7A—C18A—H18A109.5C7B—C18B—H18D109.5
C7A—C18A—H18B109.5C7B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
C7A—C18A—H18C109.5C7B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
C24A—C19A—C20A116.9 (3)C20B—C19B—C24B116.8 (3)
C24A—C19A—C15A124.6 (3)C20B—C19B—C15B119.6 (3)
C20A—C19A—C15A118.4 (3)C24B—C19B—C15B123.6 (3)
C21A—C20A—C19A122.0 (3)C19B—C20B—C21B121.8 (4)
C21A—C20A—H20A119.0C19B—C20B—H20B119.1
C19A—C20A—H20A119.0C21B—C20B—H20B119.1
C22A—C21A—C20A120.3 (3)C22B—C21B—C20B119.5 (3)
C22A—C21A—H21A119.8C22B—C21B—H21B120.2
C20A—C21A—H21A119.8C20B—C21B—H21B120.2
C21A—C22A—C23A119.5 (3)C23B—C22B—O3B115.2 (4)
C21A—C22A—O3A114.6 (3)C23B—C22B—C21B119.4 (3)
C23A—C22A—O3A125.9 (4)O3B—C22B—C21B125.3 (4)
C22A—C23A—C24A119.6 (3)C23B—C24B—C19B122.0 (3)
C22A—C23A—H23A120.2C23B—C24B—H24B119.0
C24A—C23A—H23A120.2C19B—C24B—H24B119.0
C19A—C24A—C23A121.6 (3)C24B—C23B—C22B120.5 (4)
C19A—C24A—H24A119.2C24B—C23B—H23B119.8
C23A—C24A—H24A119.2C22B—C23B—H23B119.8
O3A—C25A—H25A109.5O3B—C25B—H25D109.5
O3A—C25A—H25B109.5O3B—C25B—H25E109.5
H25A—C25A—H25B109.5H25D—C25B—H25E109.5
O3A—C25A—H25C109.5O3B—C25B—H25F109.5
H25A—C25A—H25C109.5H25D—C25B—H25F109.5
H25B—C25A—H25C109.5H25E—C25B—H25F109.5
O1A—C26A—O2A123.3 (3)O1B—C26B—O2B123.7 (3)
O1A—C26A—C16A125.0 (3)O1B—C26B—C16B124.9 (3)
O2A—C26A—C16A111.6 (3)O2B—C26B—C16B111.3 (3)
O2A—C27A—H27A109.5O2B—C27B—H27D109.5
O2A—C27A—H27B109.5O2B—C27B—H27E109.5
H27A—C27A—H27B109.5H27D—C27B—H27E109.5
O2A—C27A—H27C109.5O2B—C27B—H27F109.5
H27A—C27A—H27C109.5H27D—C27B—H27F109.5
H27B—C27A—H27C109.5H27E—C27B—H27F109.5
C8A—N1A—C1A—C2A176.7 (4)C8B—N1B—C1B—C2B177.2 (4)
C17A—N1A—C1A—C2A4.1 (6)C17B—N1B—C1B—C2B8.2 (7)
C8A—N1A—C1A—C6A0.6 (4)C8B—N1B—C1B—C6B0.6 (4)
C17A—N1A—C1A—C6A173.2 (3)C17B—N1B—C1B—C6B169.6 (3)
N1A—C1A—C2A—C3A177.2 (4)N1B—C1B—C2B—C3B176.5 (4)
C6A—C1A—C2A—C3A0.3 (5)C6B—C1B—C2B—C3B1.0 (6)
C1A—C2A—C3A—C4A0.5 (6)C1B—C2B—C3B—C4B0.8 (7)
C2A—C3A—C4A—C5A1.1 (7)C2B—C3B—C4B—C5B0.5 (7)
C3A—C4A—C5A—C6A0.8 (6)C3B—C4B—C5B—C6B0.3 (7)
C4A—C5A—C6A—C1A0.1 (5)C4B—C5B—C6B—C1B0.5 (6)
C4A—C5A—C6A—C7A176.9 (4)C4B—C5B—C6B—C7B176.8 (4)
N1A—C1A—C6A—C5A178.0 (3)N1B—C1B—C6B—C5B177.2 (3)
C2A—C1A—C6A—C5A0.5 (5)C2B—C1B—C6B—C5B0.8 (6)
N1A—C1A—C6A—C7A0.5 (4)N1B—C1B—C6B—C7B0.0 (4)
C2A—C1A—C6A—C7A177.1 (3)C2B—C1B—C6B—C7B178.0 (3)
C5A—C6A—C7A—C8A177.3 (4)C5B—C6B—C7B—C8B176.0 (4)
C1A—C6A—C7A—C8A0.3 (4)C1B—C6B—C7B—C8B0.6 (4)
C5A—C6A—C7A—C18A1.8 (6)C5B—C6B—C7B—C18B4.0 (6)
C1A—C6A—C7A—C18A178.8 (3)C1B—C6B—C7B—C18B179.4 (3)
C6A—C7A—C8A—N1A0.1 (4)C6B—C7B—C8B—N1B0.9 (4)
C18A—C7A—C8A—N1A179.1 (3)C18B—C7B—C8B—N1B179.0 (3)
C6A—C7A—C8A—C9A174.3 (4)C6B—C7B—C8B—C9B172.5 (4)
C18A—C7A—C8A—C9A4.7 (7)C18B—C7B—C8B—C9B7.5 (7)
C1A—N1A—C8A—C7A0.4 (4)C1B—N1B—C8B—C7B1.0 (4)
C17A—N1A—C8A—C7A174.5 (3)C17B—N1B—C8B—C7B172.2 (3)
C1A—N1A—C8A—C9A175.8 (3)C1B—N1B—C8B—C9B174.5 (3)
C17A—N1A—C8A—C9A1.6 (4)C17B—N1B—C8B—C9B3.2 (4)
C10A—N2A—C9A—C8A46.8 (4)C10B—N2B—C9B—C8B44.1 (4)
C14A—N2A—C9A—C8A84.2 (3)C14B—N2B—C9B—C8B86.6 (3)
C10A—N2A—C9A—C16A160.7 (3)C10B—N2B—C9B—C16B157.9 (3)
C14A—N2A—C9A—C16A29.7 (3)C14B—N2B—C9B—C16B27.1 (3)
C7A—C8A—C9A—N2A75.8 (5)C7B—C8B—C9B—N2B79.4 (5)
N1A—C8A—C9A—N2A109.7 (3)N1B—C8B—C9B—N2B107.2 (3)
C7A—C8A—C9A—C16A170.2 (4)C7B—C8B—C9B—C16B166.7 (4)
N1A—C8A—C9A—C16A4.2 (3)N1B—C8B—C9B—C16B6.7 (3)
C14A—N2A—C10A—C11A55.9 (4)C14B—N2B—C10B—C11B57.3 (4)
C9A—N2A—C10A—C11A176.8 (3)C9B—N2B—C10B—C11B175.3 (3)
N2A—C10A—C11A—C12A54.1 (4)N2B—C10B—C11B—C12B53.9 (4)
C10A—C11A—C12A—C13A55.8 (4)C10B—C11B—C12B—C13B54.7 (4)
C11A—C12A—C13A—C14A56.6 (4)C11B—C12B—C13B—C14B55.9 (4)
C10A—N2A—C14A—C13A57.1 (3)C10B—N2B—C14B—C13B58.8 (3)
C9A—N2A—C14A—C13A171.2 (2)C9B—N2B—C14B—C13B169.4 (2)
C10A—N2A—C14A—C15A179.4 (2)C10B—N2B—C14B—C15B178.0 (3)
C9A—N2A—C14A—C15A47.6 (3)C9B—N2B—C14B—C15B46.2 (3)
C12A—C13A—C14A—N2A55.6 (4)C12B—C13B—C14B—N2B56.5 (4)
C12A—C13A—C14A—C15A168.5 (3)C12B—C13B—C14B—C15B170.0 (3)
N2A—C14A—C15A—C19A172.6 (3)N2B—C14B—C15B—C19B172.0 (3)
C13A—C14A—C15A—C19A69.0 (4)C13B—C14B—C15B—C19B69.7 (4)
N2A—C14A—C15A—C16A44.9 (3)N2B—C14B—C15B—C16B44.9 (3)
C13A—C14A—C15A—C16A163.3 (3)C13B—C14B—C15B—C16B163.2 (3)
C19A—C15A—C16A—C26A83.2 (3)C19B—C15B—C16B—C26B82.8 (3)
C14A—C15A—C16A—C26A145.8 (3)C14B—C15B—C16B—C26B147.6 (3)
C19A—C15A—C16A—C17A43.4 (4)C19B—C15B—C16B—C17B43.7 (3)
C14A—C15A—C16A—C17A87.6 (3)C14B—C15B—C16B—C17B86.0 (3)
C19A—C15A—C16A—C9A158.4 (2)C19B—C15B—C16B—C9B158.3 (3)
C14A—C15A—C16A—C9A27.5 (3)C14B—C15B—C16B—C9B28.6 (3)
N2A—C9A—C16A—C26A120.8 (3)N2B—C9B—C16B—C26B123.1 (3)
C8A—C9A—C16A—C26A115.1 (3)C8B—C9B—C16B—C26B112.7 (3)
N2A—C9A—C16A—C17A118.9 (3)N2B—C9B—C16B—C17B116.5 (3)
C8A—C9A—C16A—C17A5.2 (3)C8B—C9B—C16B—C17B7.7 (3)
N2A—C9A—C16A—C15A0.1 (3)N2B—C9B—C16B—C15B2.1 (3)
C8A—C9A—C16A—C15A124.0 (2)C8B—C9B—C16B—C15B126.3 (2)
C1A—N1A—C17A—C16A170.5 (3)C8B—N1B—C17B—C16B2.0 (4)
C8A—N1A—C17A—C16A1.8 (4)C1B—N1B—C17B—C16B166.4 (3)
C26A—C16A—C17A—N1A115.1 (3)C26B—C16B—C17B—N1B113.7 (3)
C15A—C16A—C17A—N1A117.2 (3)C15B—C16B—C17B—N1B118.7 (3)
C9A—C16A—C17A—N1A4.3 (3)C9B—C16B—C17B—N1B6.1 (3)
C14A—C15A—C19A—C24A6.4 (5)C14B—C15B—C19B—C20B165.9 (3)
C16A—C15A—C19A—C24A115.3 (3)C16B—C15B—C19B—C20B73.5 (4)
C14A—C15A—C19A—C20A171.4 (3)C14B—C15B—C19B—C24B12.3 (5)
C16A—C15A—C19A—C20A66.9 (4)C16B—C15B—C19B—C24B108.4 (3)
C24A—C19A—C20A—C21A0.0 (5)C24B—C19B—C20B—C21B0.5 (5)
C15A—C19A—C20A—C21A178.0 (3)C15B—C19B—C20B—C21B178.8 (3)
C19A—C20A—C21A—C22A0.0 (5)C19B—C20B—C21B—C22B0.4 (5)
C20A—C21A—C22A—C23A0.4 (5)C25B—O3B—C22B—C23B177.9 (3)
C20A—C21A—C22A—O3A179.1 (3)C25B—O3B—C22B—C21B2.2 (5)
C25A—O3A—C22A—C21A174.3 (3)C20B—C21B—C22B—C23B0.1 (5)
C25A—O3A—C22A—C23A6.3 (5)C20B—C21B—C22B—O3B179.9 (3)
C21A—C22A—C23A—C24A0.6 (5)C20B—C19B—C24B—C23B0.4 (5)
O3A—C22A—C23A—C24A178.8 (3)C15B—C19B—C24B—C23B178.7 (3)
C20A—C19A—C24A—C23A0.2 (5)C19B—C24B—C23B—C22B0.2 (5)
C15A—C19A—C24A—C23A177.6 (3)O3B—C22B—C23B—C24B180.0 (3)
C22A—C23A—C24A—C19A0.5 (5)C21B—C22B—C23B—C24B0.0 (5)
C27A—O2A—C26A—O1A0.6 (5)C27B—O2B—C26B—O1B0.4 (5)
C27A—O2A—C26A—C16A179.3 (3)C27B—O2B—C26B—C16B179.6 (3)
C17A—C16A—C26A—O1A9.1 (5)C17B—C16B—C26B—O1B7.0 (5)
C15A—C16A—C26A—O1A136.4 (4)C15B—C16B—C26B—O1B134.2 (4)
C9A—C16A—C26A—O1A108.8 (4)C9B—C16B—C26B—O1B110.7 (4)
C17A—C16A—C26A—O2A172.2 (3)C17B—C16B—C26B—O2B173.8 (3)
C15A—C16A—C26A—O2A44.9 (4)C15B—C16B—C26B—O2B46.6 (4)
C9A—C16A—C26A—O2A69.9 (3)C9B—C16B—C26B—O2B68.5 (3)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C19A–C24A and C19B–C24B rings, respectively.
D—H···AD—HH···AD···AD—H···A
C17B—H17C···O1B0.972.362.825 (4)109
C17A—H17A···O1A0.972.382.841 (4)109
C15B—H15B···O2B0.982.392.857 (4)109
C15A—H15A···O2A0.982.372.858 (4)110
C25A—H25A···Cg1i0.962.813.606 (5)141
C25B—H25F···Cg2ii0.962.683.495 (5)143
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+2, y+1, z.
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C19A–C24A and C19B–C24B rings, respectively.
D—H···AD—HH···AD···AD—H···A
C25A—H25A···Cg1i0.962.813.606 (5)141
C25B—H25F···Cg2ii0.962.683.495 (5)143
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+2, y+1, z.
Acknowledgements top

SS acknowledges the Department of Science and Technology (DST), India, for providing computing facilities under the DST-Fast Track Scheme. SS also thanks the Vice Chancellor and Management of the Kalasalingam University, Krishnankoil, for their support and encouragement.

references
References top

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