supplementary materials


rk2391 scheme

Acta Cryst. (2013). E69, o317    [ doi:10.1107/S1600536813002043 ]

1'-(1,3-Diphenyl-1H-pyrazol-4-yl)-1''-methyl-2',3',5',6',7',7a'-octahydro-1'H-dispiro[1-benzopyran-3,2'-pyrrolizine-3',3''-indoline]-2'',4-dione

G. Jagadeesan, K. Sethusankar, D. Kathirvelan, J. Haribabu and B. S. R. Reddy

Abstract top

In the title compound C38H32N4O3, one pyrrolidine ring adopts an envelope conformation with the N atom as the flap while other pyrrolidine ring adopts an twisted conformation. The pyrrolizine ring forms dihedral angles of 79.24 (5) and 77.57 (5)° with the chromene and indole rings, respectively. The carbonyl O atoms deviate from the least-square planes through the chromene and indole rings by 0.0113 (12) and 0.0247 (12) Å, respectively. In the crystal, non-classical C-H...O interactions link the molecules, generating an C(9) chain along the b-axis direction.

Comment top

Pyrazole derivatives in general are well known nitrogen containing heterocyclic compounds and these derivatives have been the subject of enormous research due to their importance in various applications and their widespread potential biological and pharmacological activities such as antimicrobial (Mahajan et al., 1991), antiviral (Baraldi et al., 1998), antitumor (Katayama & Oshiyama, 1997), antifungal activities (Chen & Li, 1998).

The molecular structure of the title compound C38H32N4O3, is shown in Fig. 1. The phenyl rings (C1-C6) and (C8-C13) attached with the pyrazole ring (C7/C14/C15/N4/N5) form a dihedral angle of 52.60 (6)° between them. The pyrazole ring (C7/C14/C15/N4/N5) forms dihedral angles of 41.24 (6)° and 12.85 (5)° with the two phenyl rings (C1-C6) and (C8-C13), respectively. The pyrrolizine ring (C16-C21/C30/N1) forms dihedral angles of 79.24 (5)° and 77.57 (5)° with the chromene ring (C30-C38/O1) and indole ring (C21-C27/C29/N3), respectively. The atoms C28, O3 and O2 deviate from the l.s. planes of the indole ring (C21-C27/C29/N3) and chromene ring (C30-C38/O1) by 0.020 (2)Å, 0.0247 (12)Å and 0.0113 (12)Å, respectively. The title compound exhibits the structural similarities with the already reported related structure (Fun et al., 2011).

The sum of angles around the N1 atom (340°) indicates sp3 hybridization. The pyrrolidine ring (C16/C17/C21/C30/N1) adopts an envelope conformation on N1 with puckering parameters (Cremer & Pople, 1975) of q2 = 0.3225 (15)Å and φ2= 186.4 (3)°. Also, the atom N1 deviates from the mean planes of the remaining ring atoms by -0.2027 (14)Å. The other pyrrolidine ring (C17-C20/N1) adopts a twisted conformation on C17 and C18 with puckering parameters of q2 = 0.294 (2)Å and φ2 = 236.2 (4)°. Also, the atoms C17 and C18 deviate from the mean planes of the remaining ring atoms by 0.1743 (17)Å and -0.179 (2)Å.

The crystal packing is stabilized by non-classical C–H···O interactions (Table 1). The C34-H33···O3i interaction generates a C(9) chain along the b axis. The symmetry code: (i) x, y+1, z. The packing view of the compound is shown in Fig. 2.

Related literature top

For the biological activity of pyrazole derivatives, see: Mahajan et al. (1991); Baraldi et al. (1998); Katayama & Oshiyama (1997); Chen & Li (1998). For a related structure, see: Fun et al. (2011). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of methyl isatin (1.05 mmol), sarcosine (1.1 mmol), dipolarophile (1.0 mmol) in ethanol was refluxed for 85 min and cooled to room temperature. Then the mixture was poured into crushed ice breaker and the solid formed in the mixture was filtered, dried, and recrystallized from ethanol to obtain the pure product in good yield 93%.

Refinement top

Hydrogen atoms were placed in calculated positions with C–H = 0.93-0.98Å and refined in the riding model with fixed isotropic displacement parameters: Uiso(H) = 1.5Ueq(C) for methyl group and Uiso(H) = 1.2Ueq(C) for other groups.

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed down a axis, dashed lines indicates C–H···O interactions. H atoms not involved in hydrogen bonds have been excluded for clarity.
1'-(1,3-Diphenyl-1H-pyrazol-4-yl)-1''-methyl-2',3',5',6',7',7a'-octahydro-1'H-dispiro[1-benzopyran-3,2'-pyrrolizine-3',3''-indoline]-2'',4-dione top
Crystal data top
C38H32N4O3Z = 2
Mr = 592.68F(000) = 624
Triclinic, P1Dx = 1.340 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.8240 (3) ÅCell parameters from 9340 reflections
b = 10.8382 (3) Åθ = 2.1–31.2°
c = 13.9127 (4) ŵ = 0.09 mm1
α = 70.290 (1)°T = 295 K
β = 88.946 (2)°Block, colourless
γ = 73.578 (1)°0.30 × 0.25 × 0.20 mm
V = 1468.47 (7) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer
9340 independent reflections
Radiation source: fine-focus sealed tube5865 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scansθmax = 31.2°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1515
Tmin = 0.975, Tmax = 0.983k = 1515
35301 measured reflectionsl = 2019
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0793P)2 + 0.1729P]
where P = (Fo2 + 2Fc2)/3
9340 reflections(Δ/σ)max < 0.001
406 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C38H32N4O3γ = 73.578 (1)°
Mr = 592.68V = 1468.47 (7) Å3
Triclinic, P1Z = 2
a = 10.8240 (3) ÅMo Kα radiation
b = 10.8382 (3) ŵ = 0.09 mm1
c = 13.9127 (4) ÅT = 295 K
α = 70.290 (1)°0.30 × 0.25 × 0.20 mm
β = 88.946 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
9340 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
5865 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.983Rint = 0.032
35301 measured reflectionsθmax = 31.2°
Refinement top
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.166Δρmax = 0.35 e Å3
S = 1.06Δρmin = 0.25 e Å3
9340 reflectionsAbsolute structure: ?
406 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C11.20015 (16)0.45544 (16)0.12448 (12)0.0447 (4)
H11.12290.50380.14210.054*
C21.3123 (2)0.4889 (2)0.13459 (15)0.0582 (5)
H21.31020.55940.15890.070*
C31.4264 (2)0.4182 (2)0.10881 (18)0.0723 (6)
H31.50220.43890.11740.087*
C41.42844 (19)0.3164 (2)0.07008 (19)0.0758 (6)
H41.50540.27020.05070.091*
C51.31727 (17)0.28249 (19)0.05992 (15)0.0543 (4)
H51.31970.21340.03380.065*
C61.20183 (14)0.35058 (14)0.08829 (11)0.0365 (3)
C71.08498 (13)0.30861 (14)0.08134 (11)0.0335 (3)
C80.90446 (14)0.17479 (14)0.03996 (11)0.0372 (3)
C90.94126 (19)0.19600 (19)0.13752 (13)0.0521 (4)
H91.00180.24310.16090.063*
C100.8874 (2)0.1466 (2)0.20098 (16)0.0649 (5)
H100.91180.16140.26740.078*
C110.7992 (2)0.0766 (2)0.16741 (17)0.0626 (5)
H110.76430.04290.21030.075*
C120.76284 (19)0.05675 (19)0.07089 (16)0.0587 (5)
H120.70180.01010.04820.070*
C130.81477 (17)0.10454 (17)0.00578 (14)0.0489 (4)
H130.78960.08960.06050.059*
C140.91574 (14)0.23330 (15)0.11587 (11)0.0380 (3)
H140.84600.20640.14640.046*
C150.99309 (13)0.28870 (14)0.15423 (11)0.0338 (3)
C160.98987 (13)0.30356 (13)0.25733 (10)0.0319 (3)
H161.06180.33830.26580.038*
C171.01160 (14)0.16187 (14)0.34315 (11)0.0374 (3)
H170.97600.10250.31940.045*
C181.15159 (16)0.08961 (18)0.38548 (13)0.0510 (4)
H18A1.16690.00880.41500.061*
H18B1.20980.10900.33230.061*
C191.16913 (18)0.1481 (2)0.46624 (16)0.0677 (6)
H19A1.22810.07890.52290.081*
H19B1.20410.22480.43800.081*
C201.03935 (16)0.1942 (2)0.50153 (13)0.0508 (4)
H20A1.03440.13450.57050.061*
H20B1.02230.28700.50150.061*
C210.82823 (13)0.30387 (14)0.38591 (10)0.0322 (3)
C220.76483 (14)0.36324 (14)0.46523 (11)0.0347 (3)
C230.79918 (15)0.43927 (16)0.51647 (11)0.0407 (3)
H230.87020.47190.49900.049*
C240.72698 (17)0.46666 (18)0.59423 (12)0.0474 (4)
H240.74980.51800.62880.057*
C250.62210 (17)0.41859 (19)0.62049 (13)0.0529 (4)
H250.57540.43680.67340.063*
C260.58482 (16)0.34373 (19)0.56975 (13)0.0502 (4)
H260.51330.31190.58730.060*
C280.53123 (18)0.1847 (2)0.43800 (18)0.0645 (5)
H27A0.47770.20360.49010.097*
H27B0.56600.08740.45500.097*
H27C0.48050.22330.37330.097*
C290.72848 (14)0.23509 (14)0.36510 (11)0.0368 (3)
C300.86386 (13)0.39982 (13)0.28047 (10)0.0294 (3)
C310.89175 (14)0.52146 (14)0.29848 (10)0.0341 (3)
C320.78405 (15)0.64959 (14)0.27149 (11)0.0378 (3)
C330.7986 (2)0.76442 (17)0.28913 (14)0.0514 (4)
H320.87750.76060.31720.062*
C340.6973 (2)0.88303 (19)0.26547 (16)0.0662 (6)
H330.70800.95900.27730.079*
C350.5800 (2)0.88894 (19)0.22412 (17)0.0663 (5)
H340.51200.96940.20800.080*
C360.56248 (19)0.77743 (18)0.20650 (15)0.0551 (4)
H350.48310.78190.17890.066*
C370.66482 (15)0.65802 (15)0.23050 (12)0.0396 (3)
C380.75803 (14)0.45991 (14)0.19302 (11)0.0352 (3)
H37A0.79060.51060.13140.042*
H37B0.73630.38560.18020.042*
N10.94466 (12)0.18845 (12)0.42931 (9)0.0362 (3)
C270.65651 (14)0.31774 (15)0.49263 (11)0.0384 (3)
N30.63590 (12)0.24491 (13)0.43134 (10)0.0424 (3)
N40.95794 (12)0.22443 (12)0.02610 (9)0.0359 (3)
N51.06305 (12)0.27041 (12)0.00305 (9)0.0372 (3)
O10.64346 (10)0.54909 (10)0.21348 (8)0.0419 (3)
O20.99610 (11)0.51308 (12)0.33489 (9)0.0505 (3)
O30.73360 (11)0.17644 (12)0.30382 (9)0.0491 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0454 (9)0.0474 (8)0.0443 (9)0.0211 (7)0.0063 (7)0.0136 (7)
C20.0624 (12)0.0633 (11)0.0570 (11)0.0352 (9)0.0015 (9)0.0170 (9)
C30.0483 (11)0.0859 (15)0.0876 (16)0.0369 (11)0.0011 (10)0.0214 (12)
C40.0356 (10)0.0840 (15)0.1056 (18)0.0183 (10)0.0170 (10)0.0299 (13)
C50.0407 (9)0.0576 (10)0.0662 (12)0.0152 (8)0.0131 (8)0.0233 (9)
C60.0354 (7)0.0395 (7)0.0319 (7)0.0149 (6)0.0040 (6)0.0059 (6)
C70.0336 (7)0.0340 (6)0.0315 (7)0.0102 (5)0.0043 (5)0.0094 (5)
C80.0376 (8)0.0343 (7)0.0388 (8)0.0065 (6)0.0005 (6)0.0147 (6)
C90.0602 (11)0.0633 (10)0.0443 (9)0.0247 (9)0.0102 (8)0.0278 (8)
C100.0746 (14)0.0794 (13)0.0519 (11)0.0200 (11)0.0041 (10)0.0388 (10)
C110.0603 (12)0.0649 (11)0.0723 (13)0.0111 (9)0.0119 (10)0.0410 (10)
C120.0560 (11)0.0580 (10)0.0727 (13)0.0235 (9)0.0015 (9)0.0300 (10)
C130.0513 (10)0.0517 (9)0.0503 (10)0.0212 (8)0.0037 (8)0.0209 (8)
C140.0378 (8)0.0451 (8)0.0369 (8)0.0175 (6)0.0097 (6)0.0175 (6)
C150.0335 (7)0.0363 (7)0.0324 (7)0.0112 (5)0.0047 (5)0.0121 (5)
C160.0298 (7)0.0378 (7)0.0308 (7)0.0131 (5)0.0043 (5)0.0125 (5)
C170.0396 (8)0.0373 (7)0.0332 (7)0.0105 (6)0.0049 (6)0.0102 (6)
C180.0431 (9)0.0510 (9)0.0440 (9)0.0003 (7)0.0036 (7)0.0093 (7)
C190.0425 (10)0.0907 (15)0.0651 (13)0.0051 (10)0.0079 (9)0.0323 (11)
C200.0420 (9)0.0666 (10)0.0425 (9)0.0129 (8)0.0028 (7)0.0194 (8)
C210.0319 (7)0.0362 (6)0.0319 (7)0.0157 (5)0.0054 (5)0.0115 (5)
C220.0335 (7)0.0408 (7)0.0304 (7)0.0140 (6)0.0072 (5)0.0109 (6)
C230.0402 (8)0.0508 (8)0.0359 (8)0.0182 (7)0.0062 (6)0.0172 (7)
C240.0468 (9)0.0586 (9)0.0398 (8)0.0131 (7)0.0049 (7)0.0229 (7)
C250.0457 (9)0.0708 (11)0.0418 (9)0.0125 (8)0.0141 (7)0.0235 (8)
C260.0375 (8)0.0648 (10)0.0470 (9)0.0184 (7)0.0146 (7)0.0156 (8)
C280.0468 (10)0.0686 (12)0.0983 (16)0.0378 (9)0.0225 (10)0.0377 (11)
C290.0372 (8)0.0363 (7)0.0389 (8)0.0172 (6)0.0054 (6)0.0102 (6)
C300.0294 (6)0.0337 (6)0.0285 (6)0.0139 (5)0.0031 (5)0.0110 (5)
C310.0369 (7)0.0426 (7)0.0304 (7)0.0215 (6)0.0078 (6)0.0140 (6)
C320.0470 (9)0.0370 (7)0.0350 (7)0.0196 (6)0.0121 (6)0.0140 (6)
C330.0688 (12)0.0483 (9)0.0525 (10)0.0307 (8)0.0178 (9)0.0259 (8)
C340.0953 (17)0.0428 (9)0.0710 (13)0.0274 (10)0.0283 (12)0.0281 (9)
C350.0771 (15)0.0425 (9)0.0727 (13)0.0060 (9)0.0175 (11)0.0218 (9)
C360.0497 (10)0.0483 (9)0.0594 (11)0.0049 (7)0.0085 (8)0.0166 (8)
C370.0438 (8)0.0382 (7)0.0377 (8)0.0134 (6)0.0097 (6)0.0134 (6)
C380.0348 (7)0.0377 (7)0.0344 (7)0.0112 (6)0.0011 (6)0.0135 (6)
N10.0357 (6)0.0400 (6)0.0302 (6)0.0121 (5)0.0037 (5)0.0081 (5)
C270.0336 (7)0.0423 (7)0.0378 (8)0.0137 (6)0.0059 (6)0.0102 (6)
N30.0360 (7)0.0476 (7)0.0512 (8)0.0237 (6)0.0116 (6)0.0176 (6)
N40.0362 (6)0.0417 (6)0.0339 (6)0.0146 (5)0.0054 (5)0.0159 (5)
N50.0361 (6)0.0444 (6)0.0343 (6)0.0156 (5)0.0079 (5)0.0150 (5)
O10.0319 (5)0.0426 (5)0.0525 (6)0.0097 (4)0.0006 (5)0.0188 (5)
O20.0417 (6)0.0613 (7)0.0626 (8)0.0254 (5)0.0011 (5)0.0304 (6)
O30.0546 (7)0.0542 (6)0.0554 (7)0.0307 (6)0.0112 (6)0.0284 (6)
Geometric parameters (Å, º) top
C1—C21.383 (2)C20—H20A0.9700
C1—C61.385 (2)C20—H20B0.9700
C1—H10.9300C21—N11.4645 (18)
C2—C31.369 (3)C21—C221.518 (2)
C2—H20.9300C21—C291.5548 (19)
C3—C41.377 (3)C21—C301.5998 (18)
C3—H30.9300C22—C231.380 (2)
C4—C51.376 (3)C22—C271.395 (2)
C4—H40.9300C23—C241.387 (2)
C5—C61.385 (2)C23—H230.9300
C5—H50.9300C24—C251.373 (2)
C6—C71.475 (2)C24—H240.9300
C7—N51.3354 (18)C25—C261.379 (3)
C7—C151.4146 (19)C25—H250.9300
C8—C91.369 (2)C26—C271.372 (2)
C8—C131.380 (2)C26—H260.9300
C8—N41.4137 (18)C28—N31.446 (2)
C9—C101.385 (2)C28—H27A0.9600
C9—H90.9300C28—H27B0.9600
C10—C111.364 (3)C28—H27C0.9600
C10—H100.9300C29—O31.2157 (18)
C11—C121.356 (3)C29—N31.3553 (19)
C11—H110.9300C30—C381.5204 (19)
C12—C131.380 (2)C30—C311.5305 (18)
C12—H120.9300C31—O21.2136 (17)
C13—H130.9300C31—C321.476 (2)
C14—N41.3465 (18)C32—C371.387 (2)
C14—C151.365 (2)C32—C331.397 (2)
C14—H140.9300C33—C341.376 (3)
C15—C161.4952 (19)C33—H320.9300
C16—C171.5519 (19)C34—C351.380 (3)
C16—C301.5678 (18)C34—H330.9300
C16—H160.9800C35—C361.374 (3)
C17—N11.4587 (19)C35—H340.9300
C17—C181.519 (2)C36—C371.387 (2)
C17—H170.9800C36—H350.9300
C18—C191.502 (3)C37—O11.3595 (17)
C18—H18A0.9700C38—O11.4311 (17)
C18—H18B0.9700C38—H37A0.9700
C19—C201.486 (3)C38—H37B0.9700
C19—H19A0.9700C27—N31.400 (2)
C19—H19B0.9700N4—N51.3582 (16)
C20—N11.476 (2)
C2—C1—C6120.59 (17)N1—C21—C29103.59 (11)
C2—C1—H1119.7C22—C21—C29101.45 (11)
C6—C1—H1119.7N1—C21—C30106.50 (11)
C3—C2—C1120.08 (18)C22—C21—C30121.01 (11)
C3—C2—H2120.0C29—C21—C30110.50 (11)
C1—C2—H2120.0C23—C22—C27118.57 (13)
C2—C3—C4119.79 (18)C23—C22—C21133.02 (13)
C2—C3—H3120.1C27—C22—C21108.19 (12)
C4—C3—H3120.1C22—C23—C24119.54 (14)
C5—C4—C3120.40 (19)C22—C23—H23120.2
C5—C4—H4119.8C24—C23—H23120.2
C3—C4—H4119.8C25—C24—C23120.49 (16)
C4—C5—C6120.44 (18)C25—C24—H24119.8
C4—C5—H5119.8C23—C24—H24119.8
C6—C5—H5119.8C24—C25—C26121.14 (15)
C5—C6—C1118.64 (14)C24—C25—H25119.4
C5—C6—C7119.68 (14)C26—C25—H25119.4
C1—C6—C7121.67 (14)C27—C26—C25117.91 (15)
N5—C7—C15111.59 (12)C27—C26—H26121.0
N5—C7—C6119.80 (13)C25—C26—H26121.0
C15—C7—C6128.29 (13)N3—C28—H27A109.5
C9—C8—C13119.92 (15)N3—C28—H27B109.5
C9—C8—N4120.33 (14)H27A—C28—H27B109.5
C13—C8—N4119.74 (14)N3—C28—H27C109.5
C8—C9—C10119.34 (18)H27A—C28—H27C109.5
C8—C9—H9120.3H27B—C28—H27C109.5
C10—C9—H9120.3O3—C29—N3124.73 (14)
C11—C10—C9120.95 (19)O3—C29—C21126.96 (13)
C11—C10—H10119.5N3—C29—C21108.23 (12)
C9—C10—H10119.5C38—C30—C31106.51 (11)
C12—C11—C10119.30 (17)C38—C30—C16112.90 (11)
C12—C11—H11120.4C31—C30—C16110.79 (11)
C10—C11—H11120.4C38—C30—C21115.00 (11)
C11—C12—C13121.15 (18)C31—C30—C21108.62 (10)
C11—C12—H12119.4C16—C30—C21103.01 (10)
C13—C12—H12119.4O2—C31—C32121.27 (13)
C12—C13—C8119.34 (17)O2—C31—C30122.10 (13)
C12—C13—H13120.3C32—C31—C30116.62 (12)
C8—C13—H13120.3C37—C32—C33118.30 (15)
N4—C14—C15108.14 (13)C37—C32—C31120.90 (13)
N4—C14—H14125.9C33—C32—C31120.78 (15)
C15—C14—H14125.9C34—C33—C32120.66 (19)
C14—C15—C7104.05 (12)C34—C33—H32119.7
C14—C15—C16126.24 (13)C32—C33—H32119.7
C7—C15—C16129.14 (13)C33—C34—C35119.85 (17)
C15—C16—C17110.44 (11)C33—C34—H33120.1
C15—C16—C30117.73 (11)C35—C34—H33120.1
C17—C16—C30105.55 (10)C36—C35—C34120.85 (18)
C15—C16—H16107.6C36—C35—H34119.6
C17—C16—H16107.6C34—C35—H34119.6
C30—C16—H16107.6C35—C36—C37119.11 (19)
N1—C17—C18104.84 (12)C35—C36—H35120.4
N1—C17—C16106.34 (11)C37—C36—H35120.4
C18—C17—C16114.24 (13)O1—C37—C32121.25 (13)
N1—C17—H17110.4O1—C37—C36117.52 (15)
C18—C17—H17110.4C32—C37—C36121.23 (15)
C16—C17—H17110.4O1—C38—C30113.00 (11)
C19—C18—C17103.82 (13)O1—C38—H37A109.0
C19—C18—H18A111.0C30—C38—H37A109.0
C17—C18—H18A111.0O1—C38—H37B109.0
C19—C18—H18B111.0C30—C38—H37B109.0
C17—C18—H18B111.0H37A—C38—H37B107.8
H18A—C18—H18B109.0C17—N1—C21106.82 (11)
C20—C19—C18106.76 (15)C17—N1—C20108.47 (12)
C20—C19—H19A110.4C21—N1—C20120.70 (12)
C18—C19—H19A110.4C26—C27—C22122.34 (15)
C20—C19—H19B110.4C26—C27—N3127.43 (14)
C18—C19—H19B110.4C22—C27—N3110.23 (13)
H19A—C19—H19B108.6C29—N3—C27111.44 (12)
N1—C20—C19106.76 (14)C29—N3—C28123.50 (14)
N1—C20—H20A110.4C27—N3—C28125.06 (14)
C19—C20—H20A110.4C14—N4—N5111.74 (11)
N1—C20—H20B110.4C14—N4—C8126.92 (12)
C19—C20—H20B110.4N5—N4—C8121.34 (12)
H20A—C20—H20B108.6C7—N5—N4104.48 (11)
N1—C21—C22112.43 (11)C37—O1—C38112.91 (11)
C6—C1—C2—C30.0 (3)N1—C21—C30—C1616.80 (13)
C1—C2—C3—C41.8 (3)C22—C21—C30—C16146.76 (12)
C2—C3—C4—C51.9 (4)C29—C21—C30—C1695.07 (12)
C3—C4—C5—C60.2 (3)C38—C30—C31—O2153.47 (14)
C4—C5—C6—C11.6 (3)C16—C30—C31—O230.33 (18)
C4—C5—C6—C7177.19 (17)C21—C30—C31—O282.13 (16)
C2—C1—C6—C51.7 (2)C38—C30—C31—C3227.90 (16)
C2—C1—C6—C7177.10 (15)C16—C30—C31—C32151.04 (12)
C5—C6—C7—N537.9 (2)C21—C30—C31—C3296.50 (13)
C1—C6—C7—N5143.31 (14)O2—C31—C32—C37179.59 (14)
C5—C6—C7—C15134.98 (17)C30—C31—C32—C370.94 (19)
C1—C6—C7—C1543.8 (2)O2—C31—C32—C331.3 (2)
C13—C8—C9—C100.1 (3)C30—C31—C32—C33177.34 (13)
N4—C8—C9—C10179.90 (16)C37—C32—C33—C340.6 (2)
C8—C9—C10—C110.4 (3)C31—C32—C33—C34178.92 (16)
C9—C10—C11—C120.8 (3)C32—C33—C34—C350.2 (3)
C10—C11—C12—C130.8 (3)C33—C34—C35—C360.3 (3)
C11—C12—C13—C80.5 (3)C34—C35—C36—C370.3 (3)
C9—C8—C13—C120.2 (2)C33—C32—C37—O1178.60 (13)
N4—C8—C13—C12179.84 (15)C31—C32—C37—O10.3 (2)
N4—C14—C15—C71.22 (15)C33—C32—C37—C360.6 (2)
N4—C14—C15—C16173.21 (13)C31—C32—C37—C36178.93 (14)
N5—C7—C15—C141.20 (16)C35—C36—C37—O1179.05 (16)
C6—C7—C15—C14172.17 (14)C35—C36—C37—C320.2 (3)
N5—C7—C15—C16172.87 (13)C31—C30—C38—O157.50 (14)
C6—C7—C15—C160.5 (2)C16—C30—C38—O1179.31 (10)
C14—C15—C16—C1757.39 (18)C21—C30—C38—O162.87 (15)
C7—C15—C16—C17112.57 (15)C18—C17—N1—C21156.51 (12)
C14—C15—C16—C3063.88 (18)C16—C17—N1—C2135.16 (14)
C7—C15—C16—C30126.16 (15)C18—C17—N1—C2024.96 (16)
C15—C16—C17—N1151.63 (12)C16—C17—N1—C2096.39 (14)
C30—C16—C17—N123.37 (14)C22—C21—N1—C17167.23 (11)
C15—C16—C17—C1893.24 (15)C29—C21—N1—C1784.06 (13)
C30—C16—C17—C18138.51 (13)C30—C21—N1—C1732.52 (13)
N1—C17—C18—C1930.83 (17)C22—C21—N1—C2042.87 (17)
C16—C17—C18—C1985.18 (17)C29—C21—N1—C20151.58 (13)
C17—C18—C19—C2025.5 (2)C30—C21—N1—C2091.84 (14)
C18—C19—C20—N110.8 (2)C19—C20—N1—C179.05 (19)
N1—C21—C22—C2371.02 (19)C19—C20—N1—C21132.63 (16)
C29—C21—C22—C23178.92 (15)C25—C26—C27—C220.5 (2)
C30—C21—C22—C2356.3 (2)C25—C26—C27—N3179.74 (15)
N1—C21—C22—C27103.33 (14)C23—C22—C27—C261.3 (2)
C29—C21—C22—C276.73 (14)C21—C22—C27—C26174.04 (14)
C30—C21—C22—C27129.33 (13)C23—C22—C27—N3178.97 (13)
C27—C22—C23—C240.9 (2)C21—C22—C27—N35.73 (16)
C21—C22—C23—C24172.97 (15)O3—C29—N3—C27179.58 (14)
C22—C23—C24—C250.1 (2)C21—C29—N3—C272.63 (16)
C23—C24—C25—C260.8 (3)O3—C29—N3—C280.7 (3)
C24—C25—C26—C270.5 (3)C21—C29—N3—C28176.27 (15)
N1—C21—C29—O365.80 (18)C26—C27—N3—C29177.82 (16)
C22—C21—C29—O3177.48 (15)C22—C27—N3—C291.94 (18)
C30—C21—C29—O347.92 (19)C26—C27—N3—C281.1 (3)
N1—C21—C29—N3111.05 (13)C22—C27—N3—C28179.19 (16)
C22—C21—C29—N35.66 (14)C15—C14—N4—N50.90 (16)
C30—C21—C29—N3135.22 (12)C15—C14—N4—C8179.04 (13)
C15—C16—C30—C382.92 (16)C9—C8—N4—C14167.31 (15)
C17—C16—C30—C38120.84 (12)C13—C8—N4—C1412.7 (2)
C15—C16—C30—C31116.44 (13)C9—C8—N4—N512.6 (2)
C17—C16—C30—C31119.80 (12)C13—C8—N4—N5167.32 (13)
C15—C16—C30—C21127.57 (12)C15—C7—N5—N40.67 (15)
C17—C16—C30—C213.80 (13)C6—C7—N5—N4173.33 (12)
N1—C21—C30—C38140.06 (11)C14—N4—N5—C70.13 (15)
C22—C21—C30—C3889.97 (15)C8—N4—N5—C7179.82 (12)
C29—C21—C30—C3828.19 (16)C32—C37—O1—C3828.68 (19)
N1—C21—C30—C31100.74 (12)C36—C37—O1—C38152.08 (14)
C22—C21—C30—C3129.23 (16)C30—C38—O1—C3759.83 (15)
C29—C21—C30—C31147.40 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C34—H33···O3i0.932.593.523 (3)178
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C34—H33···O3i0.932.593.523 (3)178
Symmetry code: (i) x, y+1, z.
Acknowledgements top

The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

references
References top

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