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

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

doi:10.1107/S1600536808031206

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Pages o2052-o2053

doi:10.1107/S1600536808031206

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

M. Sathyanarayanan,^a P. Ramesh,^b Ramalingam Murugan,^c S. Sriman Narayanan ^c and M. N. Ponnuswamy ^d ^*

^aPG & Research Department of Physics, A. M. Jain College, Meenambakkam, Chennai 600 114, India, ^bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, ^cDepartment of Analytical Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^dCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 4 August 2008; accepted 26 September 2008; online 4 October 2008)

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⋯π interactions.

Related literature

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

Crystal data

C₃₁H₃₂N₂O₆·H₂O
M_r = 546.60
Hexagonal, $[R \overline 3]$
a = 38.8029 (10) Å
c = 11.0307 (3) Å
V = 14383.4 (7) Å³
Z = 18
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.23 × 0.21 × 0.17 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS, Sheldrick, 2001 ) T_min = 0.982, T_max = 0.986
111058 measured reflections
7909 independent reflections
5572 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.141
S = 1.05
7909 reflections
399 parameters
29 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86 (2)	2.419 (18)	2.8088 (18)	108 (1)
N1—H1⋯O3	0.86 (2)	2.376 (18)	2.9395 (17)	123 (1)
O4—H4B⋯O1ⁱ	0.85 (3)	2.142 (18)	2.909 (2)	150 (3)
N16—H16⋯O3ⁱⁱ	0.87 (2)	1.99 (2)	2.8449 (17)	166 (2)
C5—H5⋯O5ⁱⁱⁱ	0.98	2.45	3.3197 (18)	147
C18—H18⋯O4^iv	0.93	2.46	3.357 (2)	162
C24—H24B⋯Cg1ⁱⁱⁱ	0.93	2.93	3.776 (2)	153
Symmetry codes: (i) $[y+{\script{1\over 3}}, -x+y+{\script{2\over 3}}, -z+{\script{2\over 3}}]$ ; (ii) -x+1, -y, -z+1; (iii) $[-y+{\script{1\over 3}}, x-y-{\script{1\over 3}}, z-{\script{1\over 3}}]$ ; (iv) $[-x+y+{\script{2\over 3}}, -x+{\script{1\over 3}}, z+{\script{1\over 3}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2; 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 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808031206/ci2651sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808031206/ci2651Isup2.hkl

checkCIF report

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 Δ_s(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).

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

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·H₂O	D_x = 1.136 Mg m⁻³
M_r = 546.60	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, R3	Cell parameters from 5683 reflections
Hall symbol: -R 3	θ = 1.1–28.2°
a = 38.8029 (10) Å	µ = 0.08 mm⁻¹
c = 11.0307 (3) Å	T = 293 K
V = 14383.4 (7) Å³	Block, colourless
Z = 18	0.23 × 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 tube	5572 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω and ϕ scans	θ_max = 28.2°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS, Sheldrick, 2001)	h = −51→51
T_min = 0.982, T_max = 0.986	k = −51→51
111058 measured reflections	l = −14→14

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0548P)² + 16.9913P] where P = (F_o² + 2F_c²)/3
7909 reflections	(Δ/σ)_max = 0.001
399 parameters	Δρ_max = 0.26 e Å⁻³
29 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₃₁H₃₂N₂O₆·H₂O	Z = 18
M_r = 546.60	Mo Kα radiation
Hexagonal, R3	µ = 0.08 mm⁻¹
a = 38.8029 (10) Å	T = 293 K
c = 11.0307 (3) Å	0.23 × 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)
T_min = 0.982, T_max = 0.986	R_int = 0.035
111058 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	29 restraints
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0548P)² + 16.9913P] where P = (F_o² + 2F_c²)/3
7909 reflections	Δρ_max = 0.26 e Å⁻³
399 parameters	Δρ_min = −0.21 e Å⁻³

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.56007 (4)	0.06180 (4)	0.10291 (14)	0.0633 (4)
O2	0.56908 (4)	0.12184 (4)	0.05914 (13)	0.0619 (4)
O3	0.50835 (3)	0.01984 (3)	0.34955 (10)	0.0412 (3)
O5	0.31168 (3)	−0.07849 (4)	0.31585 (11)	0.0499 (3)
O6	0.33393 (4)	−0.13259 (3)	0.34016 (11)	0.0501 (3)
O7	0.40791 (4)	−0.11581 (4)	0.28214 (13)	0.0556 (3)
N1	0.47767 (4)	0.03182 (4)	0.11926 (11)	0.0385 (3)
H1	0.4898 (5)	0.0196 (5)	0.1441 (16)	0.041 (5)*
N16	0.47798 (4)	0.03293 (4)	0.50612 (12)	0.0400 (3)
H16	0.4835 (5)	0.0200 (6)	0.5595 (18)	0.048 (5)*
C2	0.50558 (5)	0.07457 (5)	0.12126 (13)	0.0392 (3)
H2	0.4975	0.0866	0.0572	0.047*
C3	0.50071 (4)	0.09151 (5)	0.24589 (13)	0.0376 (3)
H3	0.4867	0.1059	0.2262	0.045*
C4	0.46974 (4)	0.05359 (4)	0.31510 (12)	0.0326 (3)
C5	0.44655 (4)	0.02552 (4)	0.20623 (12)	0.0337 (3)
H5	0.4309	0.0362	0.1690	0.040*
C6	0.54749 (5)	0.08427 (6)	0.09354 (15)	0.0467 (4)
C7	0.61222 (16)	0.13632 (13)	0.0495 (5)	0.0722 (13)	0.797 (8)
H7A	0.6178	0.1242	−0.0189	0.087*	0.797 (8)
H7B	0.6221	0.1305	0.1229	0.087*	0.797 (8)
C8	0.63069 (12)	0.18077 (11)	0.0316 (6)	0.121 (2)	0.797 (8)
H8A	0.6259	0.1860	−0.0499	0.182*	0.797 (8)
H8B	0.6588	0.1935	0.0456	0.182*	0.797 (8)
H8C	0.6191	0.1910	0.0876	0.182*	0.797 (8)
C7A	0.6071 (7)	0.1388 (7)	0.0101 (16)	0.068 (5)	0.203 (8)
H7C	0.6102	0.1568	−0.0554	0.081*	0.203 (8)
H7D	0.6121	0.1184	−0.0212	0.081*	0.203 (8)
C8A	0.6359 (5)	0.1615 (6)	0.1138 (16)	0.109 (6)	0.203 (8)
H8D	0.6324	0.1434	0.1780	0.163*	0.203 (8)
H8E	0.6305	0.1816	0.1439	0.163*	0.203 (8)
H8F	0.6628	0.1739	0.0846	0.163*	0.203 (8)
C9	0.53732 (5)	0.12089 (5)	0.31560 (16)	0.0463 (4)
C10	0.54234 (7)	0.15785 (7)	0.3395 (3)	0.0837 (8)
H10	0.5233	0.1640	0.3128	0.100*
C11	0.57526 (10)	0.18618 (9)	0.4028 (4)	0.1240 (13)
H11	0.5782	0.2111	0.4177	0.149*
C12	0.60336 (9)	0.17751 (10)	0.4432 (3)	0.1093 (11)
H12	0.6255	0.1965	0.4855	0.131*
C13	0.59885 (7)	0.14127 (8)	0.4215 (2)	0.0780 (7)
H13	0.6178	0.1353	0.4496	0.094*
C14	0.56632 (5)	0.11301 (6)	0.35802 (17)	0.0554 (5)
H14	0.5638	0.0882	0.3434	0.066*
C15	0.48836 (4)	0.03372 (4)	0.38989 (13)	0.0345 (3)
C17	0.45453 (4)	0.05069 (5)	0.52273 (13)	0.0370 (3)
C18	0.44120 (5)	0.05730 (5)	0.63084 (14)	0.0469 (4)
H18	0.4468	0.0495	0.7044	0.056*
C19	0.41904 (5)	0.07617 (6)	0.62473 (15)	0.0507 (4)
H19	0.4099	0.0816	0.6960	0.061*
C20	0.41024 (5)	0.08710 (5)	0.51543 (15)	0.0446 (4)
H20	0.3951	0.0996	0.5148	0.054*
C21	0.42347 (4)	0.07994 (4)	0.40474 (13)	0.0366 (3)
C22	0.44694 (4)	0.06215 (4)	0.41045 (12)	0.0329 (3)
C23	0.41162 (5)	0.09042 (5)	0.28964 (15)	0.0430 (4)
H23	0.4249	0.0898	0.2202	0.052*
C24	0.38483 (8)	0.10039 (9)	0.2753 (2)	0.0826 (8)
H24A	0.3707	0.1015	0.3419	0.099*
H24B	0.3796	0.1065	0.1984	0.099*
C25	0.41775 (4)	−0.01738 (4)	0.23731 (12)	0.0344 (3)
C26	0.37872 (4)	−0.02733 (5)	0.26238 (13)	0.0363 (3)
H26	0.3714	−0.0079	0.2588	0.044*
C27	0.35070 (4)	−0.06595 (5)	0.29254 (13)	0.0377 (3)
C28	0.36146 (5)	−0.09500 (5)	0.30097 (14)	0.0392 (3)
C29	0.40046 (5)	−0.08511 (5)	0.27477 (14)	0.0401 (3)
C30	0.42853 (5)	−0.04645 (5)	0.24184 (14)	0.0396 (3)
H30	0.4544	−0.0401	0.2230	0.048*
C31	0.29816 (5)	−0.05142 (6)	0.29070 (19)	0.0546 (5)
H31A	0.2701	−0.0640	0.3062	0.082*
H31B	0.3032	−0.0435	0.2072	0.082*
H31C	0.3120	−0.0284	0.3416	0.082*
C32	0.31732 (7)	−0.16139 (7)	0.2477 (2)	0.0876 (9)
H32A	0.2983	−0.1865	0.2822	0.131*
H32B	0.3380	−0.1639	0.2085	0.131*
H32C	0.3044	−0.1533	0.1894	0.131*
C33	0.44799 (6)	−0.10687 (6)	0.2791 (2)	0.0670 (6)
H33A	0.4490	−0.1309	0.2889	0.100*
H33B	0.4625	−0.0888	0.3437	0.100*
H33C	0.4597	−0.0948	0.2028	0.100*
O4	0.31014 (5)	0.11716 (5)	0.52433 (13)	0.0667 (4)
H4A	0.3088 (8)	0.1132 (9)	0.6004 (10)	0.110 (11)*
H4B	0.3348 (4)	0.1306 (9)	0.507 (2)	0.122 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0469 (7)	0.0699 (9)	0.0813 (10)	0.0354 (7)	0.0131 (7)	0.0068 (7)
O2	0.0454 (7)	0.0612 (8)	0.0703 (9)	0.0201 (6)	0.0217 (6)	0.0187 (7)
O3	0.0417 (6)	0.0510 (7)	0.0404 (6)	0.0303 (5)	0.0012 (5)	0.0064 (5)
O5	0.0351 (6)	0.0546 (7)	0.0608 (7)	0.0231 (6)	0.0113 (5)	0.0135 (6)
O6	0.0465 (7)	0.0408 (6)	0.0553 (7)	0.0161 (5)	0.0091 (5)	0.0048 (5)
O7	0.0459 (7)	0.0424 (7)	0.0841 (9)	0.0262 (6)	0.0031 (6)	0.0014 (6)
N1	0.0389 (7)	0.0463 (8)	0.0349 (6)	0.0247 (6)	0.0067 (5)	0.0077 (5)
N16	0.0442 (7)	0.0492 (8)	0.0330 (6)	0.0281 (7)	−0.0007 (5)	0.0077 (6)
C2	0.0381 (8)	0.0459 (9)	0.0357 (7)	0.0226 (7)	0.0052 (6)	0.0112 (6)
C3	0.0355 (8)	0.0409 (8)	0.0398 (8)	0.0218 (7)	0.0056 (6)	0.0095 (6)
C4	0.0295 (7)	0.0374 (8)	0.0331 (7)	0.0184 (6)	0.0013 (5)	0.0054 (6)
C5	0.0321 (7)	0.0427 (8)	0.0307 (7)	0.0219 (7)	0.0010 (5)	0.0049 (6)
C6	0.0409 (9)	0.0566 (11)	0.0407 (8)	0.0231 (8)	0.0088 (7)	0.0068 (7)
C7	0.043 (2)	0.079 (2)	0.078 (3)	0.0183 (18)	0.019 (2)	0.013 (2)
C8	0.073 (2)	0.080 (3)	0.164 (5)	0.0039 (19)	0.033 (3)	0.003 (3)
C7A	0.050 (7)	0.077 (8)	0.069 (8)	0.026 (5)	0.003 (6)	0.024 (6)
C8A	0.089 (8)	0.114 (10)	0.111 (10)	0.042 (7)	0.006 (7)	−0.015 (7)
C9	0.0394 (9)	0.0424 (9)	0.0493 (9)	0.0146 (7)	0.0091 (7)	0.0039 (7)
C10	0.0583 (13)	0.0541 (13)	0.134 (2)	0.0244 (11)	−0.0018 (14)	−0.0212 (14)
C11	0.085 (2)	0.0677 (18)	0.199 (4)	0.0227 (16)	−0.010 (2)	−0.057 (2)
C12	0.0620 (16)	0.101 (2)	0.129 (3)	0.0137 (16)	−0.0146 (16)	−0.050 (2)
C13	0.0464 (12)	0.0876 (18)	0.0723 (14)	0.0127 (11)	−0.0080 (10)	−0.0029 (12)
C14	0.0428 (10)	0.0570 (11)	0.0559 (10)	0.0170 (9)	−0.0032 (8)	0.0038 (8)
C15	0.0306 (7)	0.0368 (8)	0.0356 (7)	0.0165 (6)	−0.0016 (5)	0.0049 (6)
C17	0.0352 (8)	0.0393 (8)	0.0357 (7)	0.0181 (7)	0.0010 (6)	0.0039 (6)
C18	0.0512 (10)	0.0565 (10)	0.0331 (7)	0.0271 (8)	0.0021 (7)	0.0032 (7)
C19	0.0534 (10)	0.0622 (11)	0.0385 (8)	0.0304 (9)	0.0083 (7)	−0.0018 (7)
C20	0.0424 (9)	0.0494 (9)	0.0472 (9)	0.0268 (8)	0.0073 (7)	0.0005 (7)
C21	0.0333 (7)	0.0380 (8)	0.0387 (7)	0.0180 (6)	0.0038 (6)	0.0037 (6)
C22	0.0305 (7)	0.0347 (7)	0.0322 (7)	0.0154 (6)	0.0020 (5)	0.0036 (5)
C23	0.0446 (9)	0.0526 (10)	0.0425 (8)	0.0324 (8)	0.0042 (7)	0.0052 (7)
C24	0.0934 (17)	0.149 (2)	0.0544 (12)	0.0973 (19)	0.0075 (11)	0.0120 (13)
C25	0.0329 (7)	0.0418 (8)	0.0292 (6)	0.0193 (6)	−0.0002 (5)	0.0013 (6)
C26	0.0367 (8)	0.0432 (8)	0.0340 (7)	0.0236 (7)	0.0018 (6)	0.0034 (6)
C27	0.0317 (7)	0.0483 (9)	0.0321 (7)	0.0194 (7)	0.0031 (5)	0.0020 (6)
C28	0.0381 (8)	0.0400 (8)	0.0355 (7)	0.0164 (7)	0.0023 (6)	0.0005 (6)
C29	0.0406 (8)	0.0410 (8)	0.0418 (8)	0.0226 (7)	−0.0008 (6)	−0.0028 (6)
C30	0.0334 (8)	0.0447 (9)	0.0432 (8)	0.0213 (7)	0.0017 (6)	−0.0012 (6)
C31	0.0411 (9)	0.0628 (12)	0.0665 (11)	0.0310 (9)	0.0115 (8)	0.0136 (9)
C32	0.0689 (15)	0.0558 (13)	0.0984 (18)	0.0013 (11)	0.0245 (13)	−0.0236 (12)
C33	0.0528 (12)	0.0571 (12)	0.1029 (17)	0.0365 (10)	0.0078 (11)	0.0063 (11)
O4	0.0785 (11)	0.0625 (9)	0.0496 (8)	0.0280 (8)	0.0013 (7)	0.0025 (7)

Geometric parameters (Å, º) top

O1—C6	1.198 (2)	C10—C11	1.387 (4)
O2—C6	1.323 (2)	C10—H10	0.93
O2—C7A	1.39 (2)	C11—C12	1.367 (5)
O2—C7	1.479 (6)	C11—H11	0.93
O3—C15	1.2281 (18)	C12—C13	1.349 (4)
O5—C27	1.3632 (18)	C12—H12	0.93
O5—C31	1.417 (2)	C13—C14	1.379 (3)
O6—C28	1.3774 (19)	C13—H13	0.93
O6—C32	1.409 (3)	C14—H14	0.93
O7—C29	1.3618 (19)	C17—C18	1.374 (2)
O7—C33	1.414 (2)	C17—C22	1.396 (2)
N1—C2	1.459 (2)	C18—C19	1.382 (3)
N1—C5	1.4639 (18)	C18—H18	0.93
N1—H1	0.864 (19)	C19—C20	1.377 (2)
N16—C15	1.3397 (19)	C19—H19	0.93
N16—C17	1.401 (2)	C20—C21	1.405 (2)
N16—H16	0.87 (2)	C20—H20	0.93
C2—C6	1.506 (2)	C21—C22	1.392 (2)
C2—C3	1.575 (2)	C21—C23	1.475 (2)
C2—H2	0.98	C23—C24	1.288 (3)
C3—C9	1.513 (2)	C23—H23	0.93
C3—C4	1.557 (2)	C24—H24A	0.93
C3—H3	0.98	C24—H24B	0.93
C4—C22	1.514 (2)	C25—C30	1.386 (2)
C4—C15	1.5344 (19)	C25—C26	1.391 (2)
C4—C5	1.568 (2)	C26—C27	1.382 (2)
C5—C25	1.509 (2)	C26—H26	0.93
C5—H5	0.98	C27—C28	1.387 (2)
C7—C8	1.514 (4)	C28—C29	1.393 (2)
C7—H7A	0.97	C29—C30	1.391 (2)
C7—H7B	0.97	C30—H30	0.93
C8—H8A	0.96	C31—H31A	0.96
C8—H8B	0.96	C31—H31B	0.96
C8—H8C	0.96	C31—H31C	0.96
C7A—C8A	1.532 (5)	C32—H32A	0.96
C7A—H7C	0.97	C32—H32B	0.96
C7A—H7D	0.97	C32—H32C	0.96
C8A—H8D	0.96	C33—H33A	0.96
C8A—H8E	0.96	C33—H33B	0.96
C8A—H8F	0.96	C33—H33C	0.96
C9—C10	1.373 (3)	O4—H4A	0.850 (10)
C9—C14	1.387 (3)	O4—H4B	0.85 (3)

C6—O2—C7A	124.8 (11)	C13—C12—H12	120.2
C6—O2—C7	114.3 (2)	C11—C12—H12	120.2
C7A—O2—C7	20.0 (6)	C12—C13—C14	120.6 (3)
C27—O5—C31	117.10 (13)	C12—C13—H13	119.7
C28—O6—C32	114.69 (15)	C14—C13—H13	119.7
C29—O7—C33	118.19 (14)	C13—C14—C9	121.1 (2)
C2—N1—C5	105.16 (12)	C13—C14—H14	119.4
C2—N1—H1	108.6 (12)	C9—C14—H14	119.4
C5—N1—H1	109.4 (12)	O3—C15—N16	125.83 (13)
C15—N16—C17	112.06 (12)	O3—C15—C4	125.81 (13)
C15—N16—H16	120.3 (13)	N16—C15—C4	108.32 (12)
C17—N16—H16	127.2 (13)	C18—C17—C22	123.46 (15)
N1—C2—C6	112.10 (14)	C18—C17—N16	127.07 (14)
N1—C2—C3	108.17 (11)	C22—C17—N16	109.45 (13)
C6—C2—C3	114.37 (13)	C17—C18—C19	116.65 (15)
N1—C2—H2	107.3	C17—C18—H18	121.7
C6—C2—H2	107.3	C19—C18—H18	121.7
C3—C2—H2	107.3	C20—C19—C18	121.46 (15)
C9—C3—C4	116.95 (12)	C20—C19—H19	119.3
C9—C3—C2	119.65 (13)	C18—C19—H19	119.3
C4—C3—C2	103.33 (12)	C19—C20—C21	121.92 (16)
C9—C3—H3	105.2	C19—C20—H20	119.0
C4—C3—H3	105.2	C21—C20—H20	119.0
C2—C3—H3	105.2	C22—C21—C20	116.93 (14)
C22—C4—C15	102.14 (11)	C22—C21—C23	123.17 (13)
C22—C4—C3	113.14 (12)	C20—C21—C23	119.89 (14)
C15—C4—C3	113.80 (12)	C21—C22—C17	119.51 (13)
C22—C4—C5	119.27 (12)	C21—C22—C4	132.54 (13)
C15—C4—C5	108.28 (12)	C17—C22—C4	107.86 (12)
C3—C4—C5	100.64 (11)	C24—C23—C21	126.75 (17)
N1—C5—C25	115.29 (12)	C24—C23—H23	116.6
N1—C5—C4	104.29 (11)	C21—C23—H23	116.6
C25—C5—C4	116.34 (11)	C23—C24—H24A	120.0
N1—C5—H5	106.8	C23—C24—H24B	120.0
C25—C5—H5	106.8	H24A—C24—H24B	120.0
C4—C5—H5	106.8	C30—C25—C26	119.79 (14)
O1—C6—O2	124.28 (16)	C30—C25—C5	123.19 (13)
O1—C6—C2	125.63 (16)	C26—C25—C5	117.02 (13)
O2—C6—C2	110.08 (15)	C27—C26—C25	120.38 (14)
O2—C7—C8	104.1 (4)	C27—C26—H26	119.8
O2—C7—H7A	110.9	C25—C26—H26	119.8
C8—C7—H7A	110.9	O5—C27—C26	124.30 (14)
O2—C7—H7B	110.9	O5—C27—C28	115.41 (14)
C8—C7—H7B	110.9	C26—C27—C28	120.29 (14)
H7A—C7—H7B	109.0	O6—C28—C27	119.52 (14)
C7—C8—H8A	109.5	O6—C28—C29	121.14 (15)
C7—C8—H8B	109.5	C27—C28—C29	119.28 (14)
H8A—C8—H8B	109.5	O7—C29—C30	124.38 (14)
C7—C8—H8C	109.5	O7—C29—C28	115.04 (14)
H8A—C8—H8C	109.5	C30—C29—C28	120.56 (14)
H8B—C8—H8C	109.5	C25—C30—C29	119.65 (14)
O2—C7A—C8A	106.2 (15)	C25—C30—H30	120.2
O2—C7A—H7C	110.5	C29—C30—H30	120.2
C8A—C7A—H7C	110.5	O5—C31—H31A	109.5
O2—C7A—H7D	110.5	O5—C31—H31B	109.5
C8A—C7A—H7D	110.5	H31A—C31—H31B	109.5
H7C—C7A—H7D	108.7	O5—C31—H31C	109.5
C7A—C8A—H8D	109.5	H31A—C31—H31C	109.5
C7A—C8A—H8E	109.5	H31B—C31—H31C	109.5
H8D—C8A—H8E	109.5	O6—C32—H32A	109.5
C7A—C8A—H8F	109.5	O6—C32—H32B	109.5
H8D—C8A—H8F	109.5	H32A—C32—H32B	109.5
H8E—C8A—H8F	109.5	O6—C32—H32C	109.5
C10—C9—C14	117.30 (19)	H32A—C32—H32C	109.5
C10—C9—C3	118.31 (18)	H32B—C32—H32C	109.5
C14—C9—C3	124.39 (16)	O7—C33—H33A	109.5
C9—C10—C11	121.2 (3)	O7—C33—H33B	109.5
C9—C10—H10	119.4	H33A—C33—H33B	109.5
C11—C10—H10	119.4	O7—C33—H33C	109.5
C12—C11—C10	120.1 (3)	H33A—C33—H33C	109.5
C12—C11—H11	120.0	H33B—C33—H33C	109.5
C10—C11—H11	120.0	H4A—O4—H4B	106.1 (15)
C13—C12—C11	119.7 (3)

C5—N1—C2—C6	149.93 (13)	C5—C4—C15—N16	−128.16 (13)
C5—N1—C2—C3	22.92 (15)	C15—N16—C17—C18	−175.19 (16)
N1—C2—C3—C9	135.98 (14)	C15—N16—C17—C22	3.36 (18)
C6—C2—C3—C9	10.3 (2)	C22—C17—C18—C19	0.3 (3)
N1—C2—C3—C4	3.84 (15)	N16—C17—C18—C19	178.67 (16)
C6—C2—C3—C4	−121.84 (14)	C17—C18—C19—C20	1.1 (3)
C9—C3—C4—C22	71.14 (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—C23	177.00 (16)
C2—C3—C4—C15	88.82 (14)	C20—C21—C22—C17	3.0 (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—C4	8.4 (3)
C2—N1—C5—C4	−40.81 (14)	C18—C17—C22—C21	−2.5 (2)
C22—C4—C5—N1	166.34 (12)	N16—C17—C22—C21	178.91 (13)
C15—C4—C5—N1	−77.61 (13)	C18—C17—C22—C4	174.44 (15)
C3—C4—C5—N1	42.03 (13)	N16—C17—C22—C4	−4.17 (17)
C22—C4—C5—C25	−65.48 (17)	C15—C4—C22—C21	179.73 (16)
C15—C4—C5—C25	50.57 (16)	C3—C4—C22—C21	57.0 (2)
C3—C4—C5—C25	170.21 (12)	C5—C4—C22—C21	−61.0 (2)
C7A—O2—C6—O1	11.2 (8)	C15—C4—C22—C17	3.37 (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—C17	122.61 (14)
C7—O2—C6—C2	170.3 (3)	C22—C21—C23—C24	167.1 (2)
N1—C2—C6—O1	−20.7 (2)	C20—C21—C23—C24	−11.5 (3)
C3—C2—C6—O1	102.9 (2)	N1—C5—C25—C30	33.13 (19)
N1—C2—C6—O2	160.55 (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—C26	90.44 (16)
C7A—O2—C7—C8	64 (3)	C30—C25—C26—C27	0.4 (2)
C6—O2—C7A—C8A	−100.1 (19)	C5—C25—C26—C27	−179.48 (13)
C7—O2—C7A—C8A	−36 (2)	C31—O5—C27—C26	9.3 (2)
C4—C3—C9—C10	−113.8 (2)	C31—O5—C27—C28	−170.80 (15)
C2—C3—C9—C10	120.2 (2)	C25—C26—C27—O5	−178.51 (14)
C4—C3—C9—C14	65.8 (2)	C25—C26—C27—C28	1.6 (2)
C2—C3—C9—C14	−60.2 (2)	C32—O6—C28—C27	103.6 (2)
C14—C9—C10—C11	0.5 (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—O6	175.03 (14)
C10—C11—C12—C13	−0.2 (6)	O5—C27—C28—C29	177.94 (14)
C11—C12—C13—C14	0.6 (5)	C26—C27—C28—C29	−2.1 (2)
C12—C13—C14—C9	−0.4 (4)	C33—O7—C29—C30	12.7 (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—O7	4.7 (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—O3	176.54 (14)	C27—C28—C29—C30	0.7 (2)
C3—C4—C15—O3	−61.2 (2)	C26—C25—C30—C29	−1.8 (2)
C5—C4—C15—O3	49.82 (19)	C5—C25—C30—C29	178.09 (14)
C22—C4—C15—N16	−1.44 (15)	O7—C29—C30—C25	−179.95 (15)
C3—C4—C15—N16	120.85 (14)	C28—C29—C30—C25	1.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86 (2)	2.419 (18)	2.8088 (18)	108 (1)
N1—H1···O3	0.86 (2)	2.376 (18)	2.9395 (17)	123 (1)
O4—H4B···O1ⁱ	0.85 (3)	2.14 (2)	2.909 (2)	150 (3)
N16—H16···O3ⁱⁱ	0.87 (2)	1.99 (2)	2.8449 (17)	166 (2)
C5—H5···O5ⁱⁱⁱ	0.98	2.45	3.3197 (18)	147
C18—H18···O4^iv	0.93	2.46	3.357 (2)	162
C24—H24B···Cg1ⁱⁱⁱ	0.93	2.93	3.776 (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.

Experimental details

Crystal data
Chemical formula	C₃₁H₃₂N₂O₆·H₂O
M_r	546.60
Crystal system, space group	Hexagonal, R3
Temperature (K)	293
a, c (Å)	38.8029 (10), 11.0307 (3)
V (Å³)	14383.4 (7)
Z	18
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.23 × 0.21 × 0.17

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS, Sheldrick, 2001)
T_min, T_max	0.982, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	111058, 7909, 5572
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.142, 1.05
No. of reflections	7909
No. of parameters	399
No. of restraints	29
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.0548P)² + 16.9913P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.21

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86 (2)	2.419 (18)	2.8088 (18)	108 (1)
N1—H1···O3	0.86 (2)	2.376 (18)	2.9395 (17)	123 (1)
O4—H4B···O1ⁱ	0.85 (3)	2.142 (18)	2.909 (2)	150 (3)
N16—H16···O3ⁱⁱ	0.87 (2)	1.99 (2)	2.8449 (17)	166 (2)
C5—H5···O5ⁱⁱⁱ	0.98	2.45	3.3197 (18)	147
C18—H18···O4^iv	0.93	2.46	3.357 (2)	162
C24—H24B···Cg1ⁱⁱⁱ	0.93	2.93	3.776 (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

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

References

Amalraj, A., Raghunathan, R., Sridevi Kumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407–419. Web of Science PubMed Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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