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Acta Cryst. (2008). E64, o2052-o2053    [ doi:10.1107/S1600536808031206 ]

Ethyl 4'-ethenyl-2'-oxo-4-phenyl-2-(3,4,5-trimethoxyphenyl)spiro[pyrrolidine-3,3'-indoline]-5-carboxylate monohydrate

M. Sathyanarayanan, P. Ramesh, R. Murugan, S. S. Narayanan and M. N. Ponnuswamy

Abstract top

In the title compound, C31H32N2O6·H2O, the pyrrolidine ring adopts an envelope conformation. The ethyl C atoms of the ethoxycabonyl group are disordered over two positions with occupancies of ca 0.80 and 0.20. Intramolecular N-H...O hydrogen bonds form S(5) and S(6) ring motifs. Molecules are linked into a three-dimensional framework by O-H...O, N-H...O and C-H...O hydrogen bonds, and by C-H...[pi] interactions.

Comment top

Substituted pyrrolidine compounds possess antimicrobial and antifungal activity against various pathogens (Amalraj et al., 2003). Several optically active pyrrolidine compounds are used as intermediates in controlled asymmetric synthesis (Suzuki et al., 1994). The spiro-indole-pyrrolidine ring system is a frequently encountered structural motif in many biologically important and pharmacologically relevant alkaloids, e.g. vincrinstine, vinblastine and spirotypostatins (Cordell, 1981). Against this background and to ascertain the detailed information on its molecular conformation, the structure determination of the title compound has been carried out.

The pyrrolidine ring (N1—C5) adopts an envelope conformation, with puckering (Cremer & Pople, 1975) and asymmetry (Nardelli, 1983) parameters q2 = 0.416 (2) Å, φ = 137.5 (2)° and Δs(C5) = 2.8 (2)°. The indoline ring system is planar and the keto atom O3 lies on the plane. The sum of angles at atom N1 of the pyrrolidine ring (323.3°) is in accordance with sp3 hybridization (Beddoes et al., 1986). The ethoxycarbonyl group is in an extended conformation as evidenced by torsion angles C2—C6—O2—C7 of -170.3 (3)° and C6—O2—C7—C8 of 170.3 (3)°.

Intramolecular N1—H1···O1 and N1—H1···O3 hydrogen bonds generate S(5) and S(6) ring motifs (Bernstein et al. 1995), respectively. The crystal packing is stabilized by O—H···O, O—H···N, N—H···O and C—H···O hydrogen bonds, and C—H···π intermolecular interactions (Table 1) which link the molecules into a three-dimensional framework.

Related literature top

For related literature, see: Amalraj et al. (2003); Beddoes et al. (1986); Cordell (1981); Suzuki et al. (1994). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

3-Arylidene-4-vinylindoline-2-one (0.5 g, 1.0 mol) and (E)-ethyl-2-(3,4,5-trimethoxybenzylideneamino)acetate (0.15 g, 1.0 mol) in acetonitrile (10 ml) was stirred in the presence of catalytic amount of AgOAc and triethylamine. The obtained crude product was recrystallized in n-hexane-acetone (8:2 v/v).

Refinement top

The ethyl C atoms of the ethoxycarbonyl group are disordered over two positions (C7/C7A and C8/C8A) with refined occupancies of 0.797 (8) and 0.203 (8). The corresponding bond distances involving the disordered atoms were restrained to 1.54 (5) Å, and also the Uij parameters of atoms C7, C7A, C8 and C8A were restrained to an approximate isotropic behaviour. The O– and N-bound H atoms were located in a difference map and refined with O—H and H···H distances restrained to 0.84 (1) and 1.37 (1) Å, respectively. The remaining H atoms were positioned geometrically (C—H = 0.93–0.98 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2–1.5(methyl) Ueq(C). A search for solvent-accessible voids in the crystal structure using PLATON showed a potential solvent volume of 2189.3 Å3 and subsequent application of SQUEEZE procedures showed three relevant voids each with a solvent-accessible volume of 730 Å3. However, this procedure showed no electrons in the voids. This indicates that the crystal lost nearly all of its solvent of crystallization by the time it was used for data collection, without collapse of the structure.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. Both disorder components are shown.
Ethyl 4'-ethenyl-2'-oxo-4-phenyl-2-(3,4,5- trimethoxyphenyl)spiro[pyrrolidine-3,3'-indoline]-5-carboxylate monohydrate top
Crystal data top
C31H32N2O6·H2ODx = 1.136 Mg m−3
Mr = 546.60Mo Kα radiation, λ = 0.71073 Å
Hexagonal, R3Cell parameters from 5683 reflections
Hall symbol: -R 3θ = 1.1–28.2°
a = 38.8029 (10) ŵ = 0.08 mm−1
c = 11.0307 (3) ÅT = 293 K
V = 14383.4 (7) Å3Block, colourless
Z = 180.23 × 0.21 × 0.17 mm
F(000) = 5220
Data collection top
Bruker Kappa APEXII area-detector
diffractometer		7909 independent reflections
Radiation source: fine-focus sealed tube5572 reflections with I > 2σ(I)
graphiteRint = 0.035
ω and φ scansθmax = 28.2°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS, Sheldrick, 2001)		h = −51→51
Tmin = 0.982, Tmax = 0.986k = −51→51
111058 measured reflectionsl = −14→14
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0548P)2 + 16.9913P]
where P = (Fo2 + 2Fc2)/3
7909 reflections(Δ/σ)max = 0.001
399 parametersΔρmax = 0.26 e Å−3
29 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C31H32N2O6·H2OZ = 18
Mr = 546.60Mo Kα radiation
Hexagonal, R3µ = 0.08 mm−1
a = 38.8029 (10) ÅT = 293 K
c = 11.0307 (3) Å0.23 × 0.21 × 0.17 mm
V = 14383.4 (7) Å3
Data collection top
Bruker Kappa APEXII area-detector
diffractometer		7909 independent reflections
Absorption correction: multi-scan
(SADABS, Sheldrick, 2001)		5572 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.986Rint = 0.035
111058 measured reflectionsθmax = 28.2°
Refinement top
R[F2 > 2σ(F2)] = 0.046 w = 1/[σ2(Fo2) + (0.0548P)2 + 16.9913P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.142Δρmax = 0.26 e Å−3
S = 1.05Δρmin = −0.21 e Å−3
7909 reflectionsAbsolute structure: ?
399 parametersFlack parameter: ?
29 restraintsRogers parameter: ?
H atoms treated by a mixture of independent and constrained refinement
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.56007 (4)0.06180 (4)0.10291 (14)0.0633 (4)
O20.56908 (4)0.12184 (4)0.05914 (13)0.0619 (4)
O30.50835 (3)0.01984 (3)0.34955 (10)0.0412 (3)
O50.31168 (3)−0.07849 (4)0.31585 (11)0.0499 (3)
O60.33393 (4)−0.13259 (3)0.34016 (11)0.0501 (3)
O70.40791 (4)−0.11581 (4)0.28214 (13)0.0556 (3)
N10.47767 (4)0.03182 (4)0.11926 (11)0.0385 (3)
H10.4898 (5)0.0196 (5)0.1441 (16)0.041 (5)*
N160.47798 (4)0.03293 (4)0.50612 (12)0.0400 (3)
H160.4835 (5)0.0200 (6)0.5595 (18)0.048 (5)*
C20.50558 (5)0.07457 (5)0.12126 (13)0.0392 (3)
H20.49750.08660.05720.047*
C30.50071 (4)0.09151 (5)0.24589 (13)0.0376 (3)
H30.48670.10590.22620.045*
C40.46974 (4)0.05359 (4)0.31510 (12)0.0326 (3)
C50.44655 (4)0.02552 (4)0.20623 (12)0.0337 (3)
H50.43090.03620.16900.040*
C60.54749 (5)0.08427 (6)0.09354 (15)0.0467 (4)
C70.61222 (16)0.13632 (13)0.0495 (5)0.0722 (13)0.797 (8)
H7A0.61780.1242−0.01890.087*0.797 (8)
H7B0.62210.13050.12290.087*0.797 (8)
C80.63069 (12)0.18077 (11)0.0316 (6)0.121 (2)0.797 (8)
H8A0.62590.1860−0.04990.182*0.797 (8)
H8B0.65880.19350.04560.182*0.797 (8)
H8C0.61910.19100.08760.182*0.797 (8)
C7A0.6071 (7)0.1388 (7)0.0101 (16)0.068 (5)0.203 (8)
H7C0.61020.1568−0.05540.081*0.203 (8)
H7D0.61210.1184−0.02120.081*0.203 (8)
C8A0.6359 (5)0.1615 (6)0.1138 (16)0.109 (6)0.203 (8)
H8D0.63240.14340.17800.163*0.203 (8)
H8E0.63050.18160.14390.163*0.203 (8)
H8F0.66280.17390.08460.163*0.203 (8)
C90.53732 (5)0.12089 (5)0.31560 (16)0.0463 (4)
C100.54234 (7)0.15785 (7)0.3395 (3)0.0837 (8)
H100.52330.16400.31280.100*
C110.57526 (10)0.18618 (9)0.4028 (4)0.1240 (13)
H110.57820.21110.41770.149*
C120.60336 (9)0.17751 (10)0.4432 (3)0.1093 (11)
H120.62550.19650.48550.131*
C130.59885 (7)0.14127 (8)0.4215 (2)0.0780 (7)
H130.61780.13530.44960.094*
C140.56632 (5)0.11301 (6)0.35802 (17)0.0554 (5)
H140.56380.08820.34340.066*
C150.48836 (4)0.03372 (4)0.38989 (13)0.0345 (3)
C170.45453 (4)0.05069 (5)0.52273 (13)0.0370 (3)
C180.44120 (5)0.05730 (5)0.63084 (14)0.0469 (4)
H180.44680.04950.70440.056*
C190.41904 (5)0.07617 (6)0.62473 (15)0.0507 (4)
H190.40990.08160.69600.061*
C200.41024 (5)0.08710 (5)0.51543 (15)0.0446 (4)
H200.39510.09960.51480.054*
C210.42347 (4)0.07994 (4)0.40474 (13)0.0366 (3)
C220.44694 (4)0.06215 (4)0.41045 (12)0.0329 (3)
C230.41162 (5)0.09042 (5)0.28964 (15)0.0430 (4)
H230.42490.08980.22020.052*
C240.38483 (8)0.10039 (9)0.2753 (2)0.0826 (8)
H24A0.37070.10150.34190.099*
H24B0.37960.10650.19840.099*
C250.41775 (4)−0.01738 (4)0.23731 (12)0.0344 (3)
C260.37872 (4)−0.02733 (5)0.26238 (13)0.0363 (3)
H260.3714−0.00790.25880.044*
C270.35070 (4)−0.06595 (5)0.29254 (13)0.0377 (3)
C280.36146 (5)−0.09500 (5)0.30097 (14)0.0392 (3)
C290.40046 (5)−0.08511 (5)0.27477 (14)0.0401 (3)
C300.42853 (5)−0.04645 (5)0.24184 (14)0.0396 (3)
H300.4544−0.04010.22300.048*
C310.29816 (5)−0.05142 (6)0.29070 (19)0.0546 (5)
H31A0.2701−0.06400.30620.082*
H31B0.3032−0.04350.20720.082*
H31C0.3120−0.02840.34160.082*
C320.31732 (7)−0.16139 (7)0.2477 (2)0.0876 (9)
H32A0.2983−0.18650.28220.131*
H32B0.3380−0.16390.20850.131*
H32C0.3044−0.15330.18940.131*
C330.44799 (6)−0.10687 (6)0.2791 (2)0.0670 (6)
H33A0.4490−0.13090.28890.100*
H33B0.4625−0.08880.34370.100*
H33C0.4597−0.09480.20280.100*
O40.31014 (5)0.11716 (5)0.52433 (13)0.0667 (4)
H4A0.3088 (8)0.1132 (9)0.6004 (10)0.110 (11)*
H4B0.3348 (4)0.1306 (9)0.507 (2)0.122 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0469 (7)0.0699 (9)0.0813 (10)0.0354 (7)0.0131 (7)0.0068 (7)
O20.0454 (7)0.0612 (8)0.0703 (9)0.0201 (6)0.0217 (6)0.0187 (7)
O30.0417 (6)0.0510 (7)0.0404 (6)0.0303 (5)0.0012 (5)0.0064 (5)
O50.0351 (6)0.0546 (7)0.0608 (7)0.0231 (6)0.0113 (5)0.0135 (6)
O60.0465 (7)0.0408 (6)0.0553 (7)0.0161 (5)0.0091 (5)0.0048 (5)
O70.0459 (7)0.0424 (7)0.0841 (9)0.0262 (6)0.0031 (6)0.0014 (6)
N10.0389 (7)0.0463 (8)0.0349 (6)0.0247 (6)0.0067 (5)0.0077 (5)
N160.0442 (7)0.0492 (8)0.0330 (6)0.0281 (7)−0.0007 (5)0.0077 (6)
C20.0381 (8)0.0459 (9)0.0357 (7)0.0226 (7)0.0052 (6)0.0112 (6)
C30.0355 (8)0.0409 (8)0.0398 (8)0.0218 (7)0.0056 (6)0.0095 (6)
C40.0295 (7)0.0374 (8)0.0331 (7)0.0184 (6)0.0013 (5)0.0054 (6)
C50.0321 (7)0.0427 (8)0.0307 (7)0.0219 (7)0.0010 (5)0.0049 (6)
C60.0409 (9)0.0566 (11)0.0407 (8)0.0231 (8)0.0088 (7)0.0068 (7)
C70.043 (2)0.079 (2)0.078 (3)0.0183 (18)0.019 (2)0.013 (2)
C80.073 (2)0.080 (3)0.164 (5)0.0039 (19)0.033 (3)0.003 (3)
C7A0.050 (7)0.077 (8)0.069 (8)0.026 (5)0.003 (6)0.024 (6)
C8A0.089 (8)0.114 (10)0.111 (10)0.042 (7)0.006 (7)−0.015 (7)
C90.0394 (9)0.0424 (9)0.0493 (9)0.0146 (7)0.0091 (7)0.0039 (7)
C100.0583 (13)0.0541 (13)0.134 (2)0.0244 (11)−0.0018 (14)−0.0212 (14)
C110.085 (2)0.0677 (18)0.199 (4)0.0227 (16)−0.010 (2)−0.057 (2)
C120.0620 (16)0.101 (2)0.129 (3)0.0137 (16)−0.0146 (16)−0.050 (2)
C130.0464 (12)0.0876 (18)0.0723 (14)0.0127 (11)−0.0080 (10)−0.0029 (12)
C140.0428 (10)0.0570 (11)0.0559 (10)0.0170 (9)−0.0032 (8)0.0038 (8)
C150.0306 (7)0.0368 (8)0.0356 (7)0.0165 (6)−0.0016 (5)0.0049 (6)
C170.0352 (8)0.0393 (8)0.0357 (7)0.0181 (7)0.0010 (6)0.0039 (6)
C180.0512 (10)0.0565 (10)0.0331 (7)0.0271 (8)0.0021 (7)0.0032 (7)
C190.0534 (10)0.0622 (11)0.0385 (8)0.0304 (9)0.0083 (7)−0.0018 (7)
C200.0424 (9)0.0494 (9)0.0472 (9)0.0268 (8)0.0073 (7)0.0005 (7)
C210.0333 (7)0.0380 (8)0.0387 (7)0.0180 (6)0.0038 (6)0.0037 (6)
C220.0305 (7)0.0347 (7)0.0322 (7)0.0154 (6)0.0020 (5)0.0036 (5)
C230.0446 (9)0.0526 (10)0.0425 (8)0.0324 (8)0.0042 (7)0.0052 (7)
C240.0934 (17)0.149 (2)0.0544 (12)0.0973 (19)0.0075 (11)0.0120 (13)
C250.0329 (7)0.0418 (8)0.0292 (6)0.0193 (6)−0.0002 (5)0.0013 (6)
C260.0367 (8)0.0432 (8)0.0340 (7)0.0236 (7)0.0018 (6)0.0034 (6)
C270.0317 (7)0.0483 (9)0.0321 (7)0.0194 (7)0.0031 (5)0.0020 (6)
C280.0381 (8)0.0400 (8)0.0355 (7)0.0164 (7)0.0023 (6)0.0005 (6)
C290.0406 (8)0.0410 (8)0.0418 (8)0.0226 (7)−0.0008 (6)−0.0028 (6)
C300.0334 (8)0.0447 (9)0.0432 (8)0.0213 (7)0.0017 (6)−0.0012 (6)
C310.0411 (9)0.0628 (12)0.0665 (11)0.0310 (9)0.0115 (8)0.0136 (9)
C320.0689 (15)0.0558 (13)0.0984 (18)0.0013 (11)0.0245 (13)−0.0236 (12)
C330.0528 (12)0.0571 (12)0.1029 (17)0.0365 (10)0.0078 (11)0.0063 (11)
O40.0785 (11)0.0625 (9)0.0496 (8)0.0280 (8)0.0013 (7)0.0025 (7)
Geometric parameters (Å, °) top
O1—C61.198 (2)C10—C111.387 (4)
O2—C61.323 (2)C10—H100.93
O2—C7A1.39 (2)C11—C121.367 (5)
O2—C71.479 (6)C11—H110.93
O3—C151.2281 (18)C12—C131.349 (4)
O5—C271.3632 (18)C12—H120.93
O5—C311.417 (2)C13—C141.379 (3)
O6—C281.3774 (19)C13—H130.93
O6—C321.409 (3)C14—H140.93
O7—C291.3618 (19)C17—C181.374 (2)
O7—C331.414 (2)C17—C221.396 (2)
N1—C21.459 (2)C18—C191.382 (3)
N1—C51.4639 (18)C18—H180.93
N1—H10.864 (19)C19—C201.377 (2)
N16—C151.3397 (19)C19—H190.93
N16—C171.401 (2)C20—C211.405 (2)
N16—H160.87 (2)C20—H200.93
C2—C61.506 (2)C21—C221.392 (2)
C2—C31.575 (2)C21—C231.475 (2)
C2—H20.98C23—C241.288 (3)
C3—C91.513 (2)C23—H230.93
C3—C41.557 (2)C24—H24A0.93
C3—H30.98C24—H24B0.93
C4—C221.514 (2)C25—C301.386 (2)
C4—C151.5344 (19)C25—C261.391 (2)
C4—C51.568 (2)C26—C271.382 (2)
C5—C251.509 (2)C26—H260.93
C5—H50.98C27—C281.387 (2)
C7—C81.514 (4)C28—C291.393 (2)
C7—H7A0.97C29—C301.391 (2)
C7—H7B0.97C30—H300.93
C8—H8A0.96C31—H31A0.96
C8—H8B0.96C31—H31B0.96
C8—H8C0.96C31—H31C0.96
C7A—C8A1.532 (5)C32—H32A0.96
C7A—H7C0.97C32—H32B0.96
C7A—H7D0.97C32—H32C0.96
C8A—H8D0.96C33—H33A0.96
C8A—H8E0.96C33—H33B0.96
C8A—H8F0.96C33—H33C0.96
C9—C101.373 (3)O4—H4A0.850 (10)
C9—C141.387 (3)O4—H4B0.85 (3)
C6—O2—C7A124.8 (11)C13—C12—H12120.2
C6—O2—C7114.3 (2)C11—C12—H12120.2
C7A—O2—C720.0 (6)C12—C13—C14120.6 (3)
C27—O5—C31117.10 (13)C12—C13—H13119.7
C28—O6—C32114.69 (15)C14—C13—H13119.7
C29—O7—C33118.19 (14)C13—C14—C9121.1 (2)
C2—N1—C5105.16 (12)C13—C14—H14119.4
C2—N1—H1108.6 (12)C9—C14—H14119.4
C5—N1—H1109.4 (12)O3—C15—N16125.83 (13)
C15—N16—C17112.06 (12)O3—C15—C4125.81 (13)
C15—N16—H16120.3 (13)N16—C15—C4108.32 (12)
C17—N16—H16127.2 (13)C18—C17—C22123.46 (15)
N1—C2—C6112.10 (14)C18—C17—N16127.07 (14)
N1—C2—C3108.17 (11)C22—C17—N16109.45 (13)
C6—C2—C3114.37 (13)C17—C18—C19116.65 (15)
N1—C2—H2107.3C17—C18—H18121.7
C6—C2—H2107.3C19—C18—H18121.7
C3—C2—H2107.3C20—C19—C18121.46 (15)
C9—C3—C4116.95 (12)C20—C19—H19119.3
C9—C3—C2119.65 (13)C18—C19—H19119.3
C4—C3—C2103.33 (12)C19—C20—C21121.92 (16)
C9—C3—H3105.2C19—C20—H20119.0
C4—C3—H3105.2C21—C20—H20119.0
C2—C3—H3105.2C22—C21—C20116.93 (14)
C22—C4—C15102.14 (11)C22—C21—C23123.17 (13)
C22—C4—C3113.14 (12)C20—C21—C23119.89 (14)
C15—C4—C3113.80 (12)C21—C22—C17119.51 (13)
C22—C4—C5119.27 (12)C21—C22—C4132.54 (13)
C15—C4—C5108.28 (12)C17—C22—C4107.86 (12)
C3—C4—C5100.64 (11)C24—C23—C21126.75 (17)
N1—C5—C25115.29 (12)C24—C23—H23116.6
N1—C5—C4104.29 (11)C21—C23—H23116.6
C25—C5—C4116.34 (11)C23—C24—H24A120.0
N1—C5—H5106.8C23—C24—H24B120.0
C25—C5—H5106.8H24A—C24—H24B120.0
C4—C5—H5106.8C30—C25—C26119.79 (14)
O1—C6—O2124.28 (16)C30—C25—C5123.19 (13)
O1—C6—C2125.63 (16)C26—C25—C5117.02 (13)
O2—C6—C2110.08 (15)C27—C26—C25120.38 (14)
O2—C7—C8104.1 (4)C27—C26—H26119.8
O2—C7—H7A110.9C25—C26—H26119.8
C8—C7—H7A110.9O5—C27—C26124.30 (14)
O2—C7—H7B110.9O5—C27—C28115.41 (14)
C8—C7—H7B110.9C26—C27—C28120.29 (14)
H7A—C7—H7B109.0O6—C28—C27119.52 (14)
C7—C8—H8A109.5O6—C28—C29121.14 (15)
C7—C8—H8B109.5C27—C28—C29119.28 (14)
H8A—C8—H8B109.5O7—C29—C30124.38 (14)
C7—C8—H8C109.5O7—C29—C28115.04 (14)
H8A—C8—H8C109.5C30—C29—C28120.56 (14)
H8B—C8—H8C109.5C25—C30—C29119.65 (14)
O2—C7A—C8A106.2 (15)C25—C30—H30120.2
O2—C7A—H7C110.5C29—C30—H30120.2
C8A—C7A—H7C110.5O5—C31—H31A109.5
O2—C7A—H7D110.5O5—C31—H31B109.5
C8A—C7A—H7D110.5H31A—C31—H31B109.5
H7C—C7A—H7D108.7O5—C31—H31C109.5
C7A—C8A—H8D109.5H31A—C31—H31C109.5
C7A—C8A—H8E109.5H31B—C31—H31C109.5
H8D—C8A—H8E109.5O6—C32—H32A109.5
C7A—C8A—H8F109.5O6—C32—H32B109.5
H8D—C8A—H8F109.5H32A—C32—H32B109.5
H8E—C8A—H8F109.5O6—C32—H32C109.5
C10—C9—C14117.30 (19)H32A—C32—H32C109.5
C10—C9—C3118.31 (18)H32B—C32—H32C109.5
C14—C9—C3124.39 (16)O7—C33—H33A109.5
C9—C10—C11121.2 (3)O7—C33—H33B109.5
C9—C10—H10119.4H33A—C33—H33B109.5
C11—C10—H10119.4O7—C33—H33C109.5
C12—C11—C10120.1 (3)H33A—C33—H33C109.5
C12—C11—H11120.0H33B—C33—H33C109.5
C10—C11—H11120.0H4A—O4—H4B106.1 (15)
C13—C12—C11119.7 (3)
C5—N1—C2—C6149.93 (13)C5—C4—C15—N16−128.16 (13)
C5—N1—C2—C322.92 (15)C15—N16—C17—C18−175.19 (16)
N1—C2—C3—C9135.98 (14)C15—N16—C17—C223.36 (18)
C6—C2—C3—C910.3 (2)C22—C17—C18—C190.3 (3)
N1—C2—C3—C43.84 (15)N16—C17—C18—C19178.67 (16)
C6—C2—C3—C4−121.84 (14)C17—C18—C19—C201.1 (3)
C9—C3—C4—C2271.14 (17)C18—C19—C20—C21−0.4 (3)
C2—C3—C4—C22−155.16 (12)C19—C20—C21—C22−1.7 (2)
C9—C3—C4—C15−44.87 (18)C19—C20—C21—C23177.00 (16)
C2—C3—C4—C1588.82 (14)C20—C21—C22—C173.0 (2)
C9—C3—C4—C5−160.45 (13)C23—C21—C22—C17−175.60 (15)
C2—C3—C4—C5−26.75 (13)C20—C21—C22—C4−172.97 (15)
C2—N1—C5—C25−169.62 (12)C23—C21—C22—C48.4 (3)
C2—N1—C5—C4−40.81 (14)C18—C17—C22—C21−2.5 (2)
C22—C4—C5—N1166.34 (12)N16—C17—C22—C21178.91 (13)
C15—C4—C5—N1−77.61 (13)C18—C17—C22—C4174.44 (15)
C3—C4—C5—N142.03 (13)N16—C17—C22—C4−4.17 (17)
C22—C4—C5—C25−65.48 (17)C15—C4—C22—C21179.73 (16)
C15—C4—C5—C2550.57 (16)C3—C4—C22—C2157.0 (2)
C3—C4—C5—C25170.21 (12)C5—C4—C22—C21−61.0 (2)
C7A—O2—C6—O111.2 (8)C15—C4—C22—C173.37 (15)
C7—O2—C6—O1−8.5 (4)C3—C4—C22—C17−119.37 (13)
C7A—O2—C6—C2−170.0 (7)C5—C4—C22—C17122.61 (14)
C7—O2—C6—C2170.3 (3)C22—C21—C23—C24167.1 (2)
N1—C2—C6—O1−20.7 (2)C20—C21—C23—C24−11.5 (3)
C3—C2—C6—O1102.9 (2)N1—C5—C25—C3033.13 (19)
N1—C2—C6—O2160.55 (14)C4—C5—C25—C30−89.46 (17)
C3—C2—C6—O2−75.85 (17)N1—C5—C25—C26−146.98 (13)
C6—O2—C7—C8−170.3 (4)C4—C5—C25—C2690.44 (16)
C7A—O2—C7—C864 (3)C30—C25—C26—C270.4 (2)
C6—O2—C7A—C8A−100.1 (19)C5—C25—C26—C27−179.48 (13)
C7—O2—C7A—C8A−36 (2)C31—O5—C27—C269.3 (2)
C4—C3—C9—C10−113.8 (2)C31—O5—C27—C28−170.80 (15)
C2—C3—C9—C10120.2 (2)C25—C26—C27—O5−178.51 (14)
C4—C3—C9—C1465.8 (2)C25—C26—C27—C281.6 (2)
C2—C3—C9—C14−60.2 (2)C32—O6—C28—C27103.6 (2)
C14—C9—C10—C110.5 (4)C32—O6—C28—C29−79.3 (2)
C3—C9—C10—C11−179.9 (3)O5—C27—C28—O6−4.9 (2)
C9—C10—C11—C12−0.4 (5)C26—C27—C28—O6175.03 (14)
C10—C11—C12—C13−0.2 (6)O5—C27—C28—C29177.94 (14)
C11—C12—C13—C140.6 (5)C26—C27—C28—C29−2.1 (2)
C12—C13—C14—C9−0.4 (4)C33—O7—C29—C3012.7 (3)
C10—C9—C14—C13−0.1 (3)C33—O7—C29—C28−168.46 (17)
C3—C9—C14—C13−179.70 (18)O6—C28—C29—O74.7 (2)
C17—N16—C15—O3−179.00 (15)C27—C28—C29—O7−178.19 (14)
C17—N16—C15—C4−1.03 (17)O6—C28—C29—C30−176.37 (14)
C22—C4—C15—O3176.54 (14)C27—C28—C29—C300.7 (2)
C3—C4—C15—O3−61.2 (2)C26—C25—C30—C29−1.8 (2)
C5—C4—C15—O349.82 (19)C5—C25—C30—C29178.09 (14)
C22—C4—C15—N16−1.44 (15)O7—C29—C30—C25−179.95 (15)
C3—C4—C15—N16120.85 (14)C28—C29—C30—C251.2 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.86 (2)2.419 (18)2.8088 (18)108 (1)
N1—H1···O30.86 (2)2.376 (18)2.9395 (17)123 (1)
O4—H4B···O1i0.85 (3)2.14 (2)2.909 (2)150 (3)
N16—H16···O3ii0.87 (2)1.99 (2)2.8449 (17)166 (2)
C5—H5···O5iii0.982.453.3197 (18)147
C18—H18···O4iv0.932.463.357 (2)162
C24—H24B···Cg1iii0.932.933.776 (2)153
Symmetry codes: (i) y+1/3, −x+y+2/3, −z+2/3; (ii) −x+1, −y, −z+1; (iii) −y+1/3, x−y−1/3, z−1/3; (iv) −x+y+2/3, −x+1/3, z+1/3.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.86 (2)2.419 (18)2.8088 (18)108 (1)
N1—H1···O30.86 (2)2.376 (18)2.9395 (17)123 (1)
O4—H4B···O1i0.85 (3)2.14 (2)2.909 (2)150 (3)
N16—H16···O3ii0.87 (2)1.99 (2)2.8449 (17)166 (2)
C5—H5···O5iii0.982.453.3197 (18)147
C18—H18···O4iv0.932.463.357 (2)162
C24—H24B···Cg1iii0.932.933.776 (2)153
Symmetry codes: (i) y+1/3, −x+y+2/3, −z+2/3; (ii) −x+1, −y, −z+1; (iii) −y+1/3, x−y−1/3, z−1/3; (iv) −x+y+2/3, −x+1/3, z+1/3.
Acknowledgements top

MS thanks Dr Babu Varghese, SAIF, IIT-Madras, India, for his help in data collection.

references
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