Ethyl 3-hydr­oxy-13-methyl-4′-phenyl-2′-(3,4,5-trimethoxy­phen­yl)-6,7,8,9,11,12,13,14,15,16-deca­hydro­spiro­[cyclo­penta­[a]phenanthrene-16,3′-pyrrolidine]-5′-carboxyl­ate

Kamala, E.T.S.; Murugan, R.; Nirmala, S.; Sudha, L.; Narayanan, S.S.

doi:10.1107/S1600536808034582

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Pages o2219-o2220

doi:10.1107/S1600536808034582

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Ethyl 3-hydroxy-13-methyl-4′-phenyl-2′-(3,4,5-trimethoxyphenyl)-6,7,8,9,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-16,3′-pyrrolidine]-5′-carboxylate

E. Theboral Sugi Kamala,^a R. Murugan,^b S. Nirmala,^a L. Sudha ^c ^* and S. Sriman Narayanan ^b

^aDepartment of Physics, Easwari Engineering College, Ramapuram, Chennai 600 089, India, ^bDepartment of Analytical Chemistry, University of Madras, Guindy Campus, Chennai 600025, India, and ^cDepartment of Physics, SRM University, Ramapuram Campus, Chennai 600 089, India
^*Correspondence e-mail: sudharose18@gmail.com

(Received 5 October 2008; accepted 23 October 2008; online 31 October 2008)

In the title compound, C₃₉H₄₅NO₇,the pyrrolidine ring is connected to an estrone group, a trimethoxy benzene and a phenyl ring. The pyrrolidine ring exhibits a twist conformation and the other five-membered ring an envelope conformation. Molecules are linked by N—H⋯O hydrogen bonds, C—H⋯π interactions and C—H⋯O hydrogen bonds.

Related literature

For general background, see: García-Peláez et al. (2004 ); Holland and Roy (1995 ); Obniska et al. (2002 ); Suzuki et al. (1994 ). For bond-length data, see: Allen et al. (1987 ). For puckering parameters, see: Cremer & Pople (1975 ). For asymmetry parameters, see: Nardelli (1983 ).

Experimental

Crystal data

C₃₉H₄₅NO₇
M_r = 639.76
Monoclinic, C 2
a = 26.1776 (6) Å
b = 10.3379 (2) Å
c = 13.6631 (3) Å
β = 91.1250 (10)°
V = 3696.82 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.30 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.977, T_max = 0.981
38566 measured reflections
3462 independent reflections
3186 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.132
S = 1.11
3462 reflections
425 parameters
319 restraints
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N1ⁱ	0.82	1.99	2.782 (4)	163
C39—H39A⋯O3ⁱⁱ	0.96	2.56	3.378 (4)	144
C29—H29A⋯Cg1ⁱⁱⁱ	0.96	3.00	3.820 (4)	144
Symmetry codes: (i) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+2]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+1]$ .

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034582/bt2805sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808034582/bt2805Isup2.hkl

checkCIF report

Comment top

Estrone is a powerful growth-inducing hormone that is present in milk, mainly in the form of fatty acid esters, at concentrations that promote growth in experimental animals (García-Peláez et al., 2004). Estrone treatment increased proliferation in mammary epithelial cells. In addition, estrone exposure altered cell cycle kinetics (Holland & Roy, 1995). Derivatives of pyrrolidine are found to have anticonvulsant properties (Obniska et al.,2002). Optically active pyrrolidines have been used as intermediates in controlled asymmetric synthesis (Suzuki et al.,1994).

Fig 1 shows the ORTEP plot of compound (I). Bond lengths and angles are comparable with other reported values (Allen et al., 1987).

In the molecule the five membered ring N1/C2/C1/C4/C3 exhibits twist conformation with assymetry parameters (Nardelli,1983) ΔC_s (C4) =15.6 (3), ΔC₂ (C2) =2.4 (3), and with the puckering parameters (Cremer and Pople,1975) q2 = 0.359 (3) Å, and ϕ2 = 125.5 (5)°. The ring C4/C5/C6/C19/C20 exhibits envelope conformation with envelope on C19 with the assymetry parameters ΔC_s(C19) = 2.4 (3) and with the puckering parameters q2 = 0.422 (3)Å and ϕ2 =110.8 (4)°

The six membered ring C9/C10/C15/C16/C17/C18 is perpendicular to the pyrrolidine ring C1/C2/N1/C3/C4 making a dihedral angle of 89.44 (11)° and planar with the five membered ring C4/C5/C6/C19/C20 with a dihedral angle of 2.20 (11).

In the crystal packing, atoms O2 and N1 are involved in intermolecular N—H···O interactions and atom O3 is involved in intermolecular C - H···O interactions. The molecules pack into distinct layers facilitated by C - H···π interactions.

Related literature top

For general background, see: García-Peláez et al. (2004); Holland and Roy (1995); Obniska et al. (2002); Suzuki et al. (1994). For bond-length data, see: Allen et al. (1987). For puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Nardelli (1983).

Experimental top

1.0 mole of (Z)-16-arylidene estrone (0.78 g) and 1.0 mol of ethyl {[(1E)-(3,4,5-trimethoxyphenyl) methylene] amino} acetate (1.0 g) was stirred in 20 ml of acetonitrile contain AgOAc (0.01 g) and triethylamine (2 ml). The reaction was allowed to stir overnight and the reaction was monitored by TLC. After the completion of reaction, the crude white solid was filtered and then purified by preparative HPLC using water and acetonitrile as eluent. The final pure compound was recrystallized using 2:8 ratio of acetone: hexane.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids.
	Fig. 2. The packing of the molecules viewed down c axis. Hydrogen bonds are indicated by dashed lines and C—H···π interactions are also shown.

Ethyl 3-hydroxy-13-methyl-4'-phenyl-2'-(3,4,5-trimethoxyphenyl)- 6,7,8,9,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene- 16,3'-pyrrolidine]-5'-carboxylate top

Crystal data top

C₃₉H₄₅NO₇	F(000) = 1368
M_r = 639.76	D_x = 1.149 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 38566 reflections
a = 26.1776 (6) Å	θ = 1.5–30.7°
b = 10.3379 (2) Å	µ = 0.08 mm⁻¹
c = 13.6631 (3) Å	T = 293 K
β = 91.125 (1)°	Prism, colourless
V = 3696.82 (14) Å³	0.30 × 0.30 × 0.25 mm
Z = 4

Data collection top

Bruker KappaAPEXII diffractometer	3462 independent reflections
Radiation source: fine-focus sealed tube	3186 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and ϕ scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (Blessing, 1995)	h = −31→31
T_min = 0.977, T_max = 0.981	k = −12→12
38566 measured reflections	l = −16→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.132	w = 1/[σ²(F_o²) + (0.082P)² + 1.3827P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max < 0.001
3462 reflections	Δρ_max = 0.48 e Å⁻³
425 parameters	Δρ_min = −0.24 e Å⁻³
319 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0112 (9)

Crystal data top

C₃₉H₄₅NO₇	V = 3696.82 (14) Å³
M_r = 639.76	Z = 4
Monoclinic, C2	Mo Kα radiation
a = 26.1776 (6) Å	µ = 0.08 mm⁻¹
b = 10.3379 (2) Å	T = 293 K
c = 13.6631 (3) Å	0.30 × 0.30 × 0.25 mm
β = 91.125 (1)°

Data collection top

Bruker KappaAPEXII diffractometer	3462 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	3186 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.981	R_int = 0.027
38566 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	319 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.11	Δρ_max = 0.48 e Å⁻³
3462 reflections	Δρ_min = −0.24 e Å⁻³
425 parameters

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
C1	0.15174 (10)	0.2439 (3)	0.8431 (2)	0.0417 (6)
H1	0.1599	0.2242	0.9117	0.050*
C2	0.11604 (10)	0.3642 (3)	0.8400 (2)	0.0460 (7)
H2	0.0836	0.3374	0.8093	0.055*
C3	0.17981 (9)	0.3995 (3)	0.7236 (2)	0.0407 (6)
H3	0.1638	0.3548	0.6676	0.049*
C4	0.20146 (9)	0.2927 (3)	0.79377 (18)	0.0367 (6)
C5	0.23722 (10)	0.3500 (3)	0.87263 (18)	0.0380 (6)
C6	0.28956 (10)	0.2904 (3)	0.86410 (19)	0.0400 (6)
C7	0.33546 (11)	0.3760 (4)	0.8831 (2)	0.0569 (8)
H7A	0.3366	0.4019	0.9514	0.068*
H7B	0.3327	0.4535	0.8433	0.068*
C8	0.38453 (11)	0.3024 (4)	0.8583 (2)	0.0591 (9)
H8A	0.4135	0.3602	0.8659	0.071*
H8B	0.3892	0.2317	0.9044	0.071*
C9	0.38342 (10)	0.2479 (3)	0.7540 (2)	0.0459 (7)
H9	0.3827	0.3227	0.7099	0.055*
C10	0.43051 (10)	0.1699 (3)	0.7281 (2)	0.0491 (7)
C11	0.47581 (11)	0.1772 (4)	0.7813 (2)	0.0525 (7)
H11	0.4775	0.2290	0.8369	0.063*
C12	0.51874 (11)	0.1095 (4)	0.7539 (3)	0.0581 (8)
H12	0.5489	0.1171	0.7905	0.070*
C13	0.51690 (11)	0.0307 (4)	0.6726 (2)	0.0568 (8)
C14	0.47166 (13)	0.0182 (5)	0.6216 (3)	0.0717 (11)
H14	0.4699	−0.0366	0.5676	0.086*
C15	0.42859 (12)	0.0850 (5)	0.6485 (2)	0.0669 (10)
C16	0.37936 (15)	0.0587 (8)	0.5916 (3)	0.118 (3)
H16A	0.3851	0.0757	0.5228	0.141*
H16B	0.3711	−0.0323	0.5979	0.141*
C17	0.33571 (11)	0.1342 (4)	0.6219 (2)	0.0580 (9)
H17A	0.3049	0.0859	0.6061	0.070*
H17B	0.3346	0.2135	0.5839	0.070*
C18	0.33529 (10)	0.1692 (3)	0.7300 (2)	0.0398 (6)
H18	0.3360	0.0896	0.7688	0.048*
C19	0.28882 (9)	0.2477 (3)	0.75683 (18)	0.0354 (5)
H19	0.2904	0.3273	0.7180	0.042*
C20	0.23490 (9)	0.1939 (3)	0.7407 (2)	0.0391 (6)
H20A	0.2317	0.1084	0.7692	0.047*
H20B	0.2260	0.1896	0.6715	0.047*
C21	0.21851 (9)	0.4925 (3)	0.68252 (19)	0.0395 (6)
C22	0.23850 (11)	0.5940 (3)	0.7375 (2)	0.0428 (6)
H22	0.2258	0.6113	0.7993	0.051*
C23	0.27723 (12)	0.6695 (3)	0.7007 (2)	0.0466 (7)
C24	0.29617 (11)	0.6431 (3)	0.6073 (2)	0.0482 (7)
C25	0.27614 (11)	0.5418 (3)	0.55345 (19)	0.0450 (7)
C26	0.23668 (10)	0.4680 (3)	0.5897 (2)	0.0423 (6)
H26	0.2224	0.4019	0.5519	0.051*
C27	0.28307 (18)	0.8008 (5)	0.8430 (3)	0.0772 (11)
H27A	0.3020	0.8736	0.8682	0.093*
H27B	0.2883	0.7277	0.8853	0.093*
H27C	0.2474	0.8218	0.8398	0.093*
C28	0.38287 (18)	0.6790 (7)	0.5804 (4)	0.1085 (19)
H28A	0.4057	0.7396	0.5509	0.130*
H28B	0.3864	0.5960	0.5497	0.130*
H28C	0.3911	0.6716	0.6490	0.130*
C29	0.28402 (16)	0.4093 (4)	0.4123 (2)	0.0656 (9)
H29A	0.3019	0.4074	0.3516	0.079*
H29B	0.2479	0.4091	0.3991	0.079*
H29C	0.2931	0.3346	0.4505	0.079*
C30	0.12845 (12)	0.1248 (3)	0.7966 (2)	0.0509 (7)
C31	0.1356 (2)	0.0062 (4)	0.8399 (4)	0.0837 (13)
H31	0.1546	0.0003	0.8979	0.100*
C32	0.1148 (3)	−0.1060 (5)	0.7983 (5)	0.120 (2)
H32	0.1199	−0.1855	0.8288	0.143*
C33	0.0873 (3)	−0.0988 (6)	0.7140 (5)	0.1109 (19)
H33	0.0732	−0.1733	0.6865	0.133*
C34	0.0803 (2)	0.0170 (6)	0.6697 (4)	0.0965 (16)
H34	0.0614	0.0216	0.6113	0.116*
C35	0.10066 (15)	0.1279 (4)	0.7099 (3)	0.0680 (10)
H35	0.0956	0.2065	0.6781	0.082*
C36	0.10410 (11)	0.4229 (4)	0.9382 (3)	0.0603 (9)
C37	0.0691 (2)	0.3797 (8)	1.0936 (4)	0.120 (2)
H37A	0.0974	0.4174	1.1306	0.144*
H37B	0.0430	0.4453	1.0846	0.144*
C38	0.0492 (3)	0.2730 (11)	1.1447 (4)	0.171 (4)
H38A	0.0373	0.3011	1.2072	0.205*
H38B	0.0754	0.2091	1.1541	0.205*
H38C	0.0213	0.2362	1.1075	0.205*
C39	0.28908 (13)	0.1760 (4)	0.9367 (2)	0.0575 (8)
H39A	0.3214	0.1320	0.9354	0.069*
H39B	0.2623	0.1170	0.9183	0.069*
H39C	0.2833	0.2079	1.0015	0.069*
N1	0.13869 (9)	0.4615 (3)	0.7770 (2)	0.0521 (7)
H1A	0.1295	0.5412	0.7721	0.062*
O1	0.22398 (8)	0.4254 (2)	0.93491 (14)	0.0518 (5)
O2	0.55830 (9)	−0.0346 (3)	0.64077 (19)	0.0773 (9)
H2A	0.5829	−0.0194	0.6771	0.093*
O3	0.10751 (10)	0.5359 (3)	0.9562 (2)	0.0814 (9)
O4	0.08664 (12)	0.3347 (3)	0.99822 (19)	0.0842 (9)
O5	0.30005 (10)	0.7705 (2)	0.74826 (17)	0.0641 (7)
O6	0.33211 (10)	0.7226 (3)	0.56819 (18)	0.0708 (7)
O7	0.29758 (9)	0.5228 (3)	0.46488 (15)	0.0590 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0373 (13)	0.0503 (15)	0.0380 (13)	0.0004 (12)	0.0077 (10)	0.0014 (12)
C2	0.0314 (13)	0.0572 (18)	0.0494 (15)	−0.0013 (12)	0.0049 (11)	−0.0071 (14)
C3	0.0294 (12)	0.0489 (15)	0.0438 (13)	0.0008 (11)	0.0005 (10)	0.0030 (13)
C4	0.0330 (12)	0.0394 (13)	0.0379 (12)	0.0011 (11)	0.0033 (10)	−0.0006 (12)
C5	0.0386 (13)	0.0412 (14)	0.0344 (12)	0.0029 (12)	0.0039 (10)	0.0009 (12)
C6	0.0368 (13)	0.0463 (15)	0.0368 (13)	0.0070 (12)	−0.0018 (10)	−0.0014 (12)
C7	0.0415 (15)	0.072 (2)	0.0566 (17)	0.0004 (15)	−0.0050 (13)	−0.0224 (17)
C8	0.0362 (14)	0.079 (2)	0.0620 (18)	−0.0012 (15)	−0.0075 (13)	−0.0192 (18)
C9	0.0325 (13)	0.0553 (17)	0.0498 (15)	0.0026 (13)	−0.0011 (11)	0.0011 (14)
C10	0.0327 (13)	0.0632 (18)	0.0513 (16)	0.0037 (13)	0.0038 (11)	0.0072 (15)
C11	0.0336 (14)	0.0558 (17)	0.0679 (19)	−0.0019 (13)	−0.0018 (12)	0.0006 (16)
C12	0.0305 (13)	0.065 (2)	0.078 (2)	0.0023 (14)	−0.0050 (13)	0.0093 (19)
C13	0.0363 (14)	0.073 (2)	0.0610 (19)	0.0101 (15)	0.0103 (13)	0.0167 (18)
C14	0.0452 (17)	0.112 (3)	0.0578 (19)	0.016 (2)	0.0070 (14)	−0.014 (2)
C15	0.0367 (15)	0.112 (3)	0.0526 (17)	0.0153 (18)	0.0035 (13)	−0.010 (2)
C16	0.050 (2)	0.225 (7)	0.078 (3)	0.037 (3)	−0.0085 (19)	−0.071 (4)
C17	0.0374 (14)	0.085 (2)	0.0515 (17)	0.0059 (16)	0.0002 (12)	−0.0226 (17)
C18	0.0317 (12)	0.0443 (14)	0.0435 (14)	0.0052 (11)	0.0028 (10)	−0.0001 (12)
C19	0.0323 (12)	0.0379 (13)	0.0359 (12)	0.0053 (11)	0.0001 (9)	−0.0016 (11)
C20	0.0327 (13)	0.0430 (15)	0.0416 (14)	0.0025 (11)	0.0021 (10)	−0.0044 (12)
C21	0.0314 (12)	0.0442 (15)	0.0427 (14)	0.0064 (11)	−0.0006 (10)	0.0054 (12)
C22	0.0426 (14)	0.0450 (15)	0.0410 (14)	0.0040 (12)	0.0073 (11)	0.0034 (12)
C23	0.0510 (16)	0.0418 (15)	0.0472 (15)	−0.0010 (13)	0.0031 (12)	0.0018 (13)
C24	0.0482 (16)	0.0516 (17)	0.0449 (15)	−0.0057 (13)	0.0066 (12)	0.0081 (13)
C25	0.0442 (15)	0.0551 (17)	0.0357 (13)	0.0044 (13)	0.0026 (11)	0.0085 (13)
C26	0.0401 (13)	0.0475 (16)	0.0391 (14)	0.0019 (12)	−0.0036 (11)	0.0058 (12)
C27	0.099 (3)	0.070 (2)	0.064 (2)	−0.024 (2)	0.017 (2)	−0.016 (2)
C28	0.061 (3)	0.145 (5)	0.120 (4)	−0.030 (3)	0.023 (3)	−0.018 (4)
C29	0.083 (2)	0.069 (2)	0.0449 (17)	0.002 (2)	0.0097 (15)	−0.0035 (16)
C30	0.0479 (16)	0.0509 (17)	0.0545 (18)	−0.0075 (14)	0.0158 (13)	0.0025 (14)
C31	0.105 (3)	0.060 (2)	0.086 (3)	−0.019 (2)	0.006 (2)	0.017 (2)
C32	0.158 (6)	0.055 (3)	0.146 (5)	−0.036 (3)	0.024 (5)	0.013 (3)
C33	0.135 (5)	0.080 (3)	0.118 (4)	−0.057 (3)	0.017 (4)	−0.015 (3)
C34	0.107 (4)	0.099 (4)	0.083 (3)	−0.052 (3)	0.004 (3)	−0.016 (3)
C35	0.075 (2)	0.065 (2)	0.064 (2)	−0.025 (2)	0.0030 (18)	−0.0038 (18)
C36	0.0352 (14)	0.080 (3)	0.066 (2)	0.0036 (16)	0.0065 (13)	−0.022 (2)
C37	0.121 (4)	0.174 (6)	0.066 (3)	0.014 (4)	0.044 (3)	−0.029 (4)
C38	0.201 (7)	0.237 (10)	0.077 (3)	0.035 (8)	0.069 (4)	0.023 (6)
C39	0.0578 (18)	0.075 (2)	0.0403 (15)	0.0201 (17)	0.0034 (13)	0.0109 (16)
N1	0.0324 (11)	0.0493 (14)	0.0749 (18)	0.0119 (11)	0.0116 (11)	0.0090 (13)
O1	0.0530 (11)	0.0588 (13)	0.0436 (10)	0.0108 (10)	0.0032 (9)	−0.0135 (10)
O2	0.0427 (12)	0.116 (2)	0.0739 (15)	0.0270 (14)	0.0088 (11)	0.0065 (16)
O3	0.0622 (15)	0.080 (2)	0.102 (2)	0.0025 (14)	0.0078 (14)	−0.0431 (18)
O4	0.099 (2)	0.096 (2)	0.0591 (14)	0.0074 (17)	0.0375 (14)	−0.0088 (15)
O5	0.0755 (15)	0.0619 (15)	0.0554 (12)	−0.0238 (13)	0.0129 (11)	−0.0080 (12)
O6	0.0726 (16)	0.0733 (17)	0.0673 (15)	−0.0251 (14)	0.0218 (12)	0.0038 (13)
O7	0.0677 (14)	0.0703 (15)	0.0396 (10)	−0.0097 (12)	0.0127 (9)	0.0016 (11)

Geometric parameters (Å, º) top

C1—C30	1.509 (4)	C20—H20B	0.9700
C1—C2	1.555 (4)	C21—C26	1.386 (4)
C1—C4	1.561 (4)	C21—C22	1.387 (4)
C1—H1	0.9800	C22—C23	1.382 (4)
C2—N1	1.458 (4)	C22—H22	0.9300
C2—C36	1.511 (4)	C23—O5	1.362 (4)
C2—H2	0.9800	C23—C24	1.404 (4)
C3—N1	1.460 (4)	C24—O6	1.366 (4)
C3—C21	1.512 (4)	C24—C25	1.378 (4)
C3—C4	1.562 (4)	C25—O7	1.358 (3)
C3—H3	0.9800	C25—C26	1.384 (4)
C4—C5	1.533 (4)	C26—H26	0.9300
C4—C20	1.536 (4)	C27—O5	1.411 (4)
C5—O1	1.210 (3)	C27—H27A	0.9600
C5—C6	1.509 (4)	C27—H27B	0.9600
C6—C7	1.511 (4)	C27—H27C	0.9600
C6—C19	1.530 (4)	C28—O6	1.410 (6)
C6—C39	1.544 (5)	C28—H28A	0.9600
C7—C8	1.537 (5)	C28—H28B	0.9600
C7—H7A	0.9700	C28—H28C	0.9600
C7—H7B	0.9700	C29—O7	1.417 (5)
C8—C9	1.532 (4)	C29—H29A	0.9600
C8—H8A	0.9700	C29—H29B	0.9600
C8—H8B	0.9700	C29—H29C	0.9600
C9—C10	1.521 (4)	C30—C31	1.373 (6)
C9—C18	1.530 (4)	C30—C35	1.378 (5)
C9—H9	0.9800	C31—C32	1.396 (7)
C10—C11	1.380 (4)	C31—H31	0.9300
C10—C15	1.399 (5)	C32—C33	1.348 (9)
C11—C12	1.382 (5)	C32—H32	0.9300
C11—H11	0.9300	C33—C34	1.353 (9)
C12—C13	1.378 (5)	C33—H33	0.9300
C12—H12	0.9300	C34—C35	1.376 (6)
C13—O2	1.356 (4)	C34—H34	0.9300
C13—C14	1.369 (5)	C35—H35	0.9300
C14—C15	1.378 (5)	C36—O3	1.197 (5)
C14—H14	0.9300	C36—O4	1.314 (5)
C15—C16	1.516 (5)	C37—C38	1.411 (12)
C16—C17	1.450 (5)	C37—O4	1.466 (5)
C16—H16A	0.9700	C37—H37A	0.9700
C16—H16B	0.9700	C37—H37B	0.9700
C17—C18	1.522 (4)	C38—H38A	0.9600
C17—H17A	0.9700	C38—H38B	0.9600
C17—H17B	0.9700	C38—H38C	0.9600
C18—C19	1.513 (4)	C39—H39A	0.9600
C18—H18	0.9800	C39—H39B	0.9600
C19—C20	1.529 (4)	C39—H39C	0.9600
C19—H19	0.9800	N1—H1A	0.8600
C20—H20A	0.9700	O2—H2A	0.8200

C30—C1—C2	113.8 (2)	C20—C19—H19	106.0
C30—C1—C4	114.6 (2)	C6—C19—H19	106.0
C2—C1—C4	103.7 (2)	C19—C20—C4	102.9 (2)
C30—C1—H1	108.2	C19—C20—H20A	111.2
C2—C1—H1	108.2	C4—C20—H20A	111.2
C4—C1—H1	108.2	C19—C20—H20B	111.2
N1—C2—C36	109.9 (3)	C4—C20—H20B	111.2
N1—C2—C1	108.4 (2)	H20A—C20—H20B	109.1
C36—C2—C1	115.6 (3)	C26—C21—C22	120.1 (3)
N1—C2—H2	107.5	C26—C21—C3	117.8 (3)
C36—C2—H2	107.5	C22—C21—C3	121.9 (2)
C1—C2—H2	107.5	C23—C22—C21	120.1 (3)
N1—C3—C21	114.3 (2)	C23—C22—H22	120.0
N1—C3—C4	105.4 (2)	C21—C22—H22	120.0
C21—C3—C4	116.1 (2)	O5—C23—C22	125.2 (3)
N1—C3—H3	106.8	O5—C23—C24	115.0 (3)
C21—C3—H3	106.8	C22—C23—C24	119.7 (3)
C4—C3—H3	106.8	O6—C24—C25	120.4 (3)
C5—C4—C20	104.1 (2)	O6—C24—C23	119.8 (3)
C5—C4—C1	108.9 (2)	C25—C24—C23	119.7 (3)
C20—C4—C1	118.5 (2)	O7—C25—C24	115.2 (3)
C5—C4—C3	111.5 (2)	O7—C25—C26	124.3 (3)
C20—C4—C3	112.6 (2)	C24—C25—C26	120.5 (3)
C1—C4—C3	101.4 (2)	C25—C26—C21	119.9 (3)
O1—C5—C6	126.2 (2)	C25—C26—H26	120.1
O1—C5—C4	124.4 (2)	C21—C26—H26	120.1
C6—C5—C4	109.3 (2)	O5—C27—H27A	109.5
C5—C6—C7	117.9 (3)	O5—C27—H27B	109.5
C5—C6—C19	101.4 (2)	H27A—C27—H27B	109.5
C7—C6—C19	109.2 (2)	O5—C27—H27C	109.5
C5—C6—C39	104.1 (2)	H27A—C27—H27C	109.5
C7—C6—C39	110.8 (3)	H27B—C27—H27C	109.5
C19—C6—C39	113.2 (3)	O6—C28—H28A	109.5
C6—C7—C8	109.7 (3)	O6—C28—H28B	109.5
C6—C7—H7A	109.7	H28A—C28—H28B	109.5
C8—C7—H7A	109.7	O6—C28—H28C	109.5
C6—C7—H7B	109.7	H28A—C28—H28C	109.5
C8—C7—H7B	109.7	H28B—C28—H28C	109.5
H7A—C7—H7B	108.2	O7—C29—H29A	109.5
C9—C8—C7	112.7 (2)	O7—C29—H29B	109.5
C9—C8—H8A	109.0	H29A—C29—H29B	109.5
C7—C8—H8A	109.0	O7—C29—H29C	109.5
C9—C8—H8B	109.0	H29A—C29—H29C	109.5
C7—C8—H8B	109.0	H29B—C29—H29C	109.5
H8A—C8—H8B	107.8	C31—C30—C35	117.1 (4)
C10—C9—C18	109.6 (3)	C31—C30—C1	119.9 (3)
C10—C9—C8	114.2 (2)	C35—C30—C1	123.0 (3)
C18—C9—C8	113.3 (2)	C30—C31—C32	121.2 (5)
C10—C9—H9	106.4	C30—C31—H31	119.4
C18—C9—H9	106.4	C32—C31—H31	119.4
C8—C9—H9	106.4	C33—C32—C31	119.9 (5)
C11—C10—C15	117.4 (3)	C33—C32—H32	120.0
C11—C10—C9	122.8 (3)	C31—C32—H32	120.0
C15—C10—C9	119.8 (2)	C32—C33—C34	119.8 (5)
C10—C11—C12	121.7 (3)	C32—C33—H33	120.1
C10—C11—H11	119.2	C34—C33—H33	120.1
C12—C11—H11	119.2	C33—C34—C35	120.7 (5)
C13—C12—C11	120.1 (3)	C33—C34—H34	119.7
C13—C12—H12	119.9	C35—C34—H34	119.7
C11—C12—H12	119.9	C34—C35—C30	121.2 (4)
O2—C13—C14	118.6 (3)	C34—C35—H35	119.4
O2—C13—C12	122.5 (3)	C30—C35—H35	119.4
C14—C13—C12	118.9 (3)	O3—C36—O4	125.1 (4)
C13—C14—C15	121.4 (4)	O3—C36—C2	124.0 (4)
C13—C14—H14	119.3	O4—C36—C2	110.8 (3)
C15—C14—H14	119.3	C38—C37—O4	108.5 (6)
C14—C15—C10	120.3 (3)	C38—C37—H37A	110.0
C14—C15—C16	117.7 (4)	O4—C37—H37A	110.0
C10—C15—C16	121.9 (3)	C38—C37—H37B	110.0
C17—C16—C15	115.1 (4)	O4—C37—H37B	110.0
C17—C16—H16A	108.5	H37A—C37—H37B	108.4
C15—C16—H16A	108.5	C37—C38—H38A	109.5
C17—C16—H16B	108.5	C37—C38—H38B	109.5
C15—C16—H16B	108.5	H38A—C38—H38B	109.5
H16A—C16—H16B	107.5	C37—C38—H38C	109.5
C16—C17—C18	115.2 (3)	H38A—C38—H38C	109.5
C16—C17—H17A	108.5	H38B—C38—H38C	109.5
C18—C17—H17A	108.5	C6—C39—H39A	109.5
C16—C17—H17B	108.5	C6—C39—H39B	109.5
C18—C17—H17B	108.5	H39A—C39—H39B	109.5
H17A—C17—H17B	107.5	C6—C39—H39C	109.5
C19—C18—C17	112.6 (2)	H39A—C39—H39C	109.5
C19—C18—C9	109.0 (2)	H39B—C39—H39C	109.5
C17—C18—C9	108.3 (2)	C2—N1—C3	107.7 (2)
C19—C18—H18	109.0	C2—N1—H1A	126.1
C17—C18—H18	109.0	C3—N1—H1A	126.1
C9—C18—H18	109.0	C13—O2—H2A	109.5
C18—C19—C20	120.9 (2)	C36—O4—C37	117.0 (4)
C18—C19—C6	113.0 (2)	C23—O5—C27	117.7 (3)
C20—C19—C6	103.7 (2)	C24—O6—C28	114.6 (4)
C18—C19—H19	106.0	C25—O7—C29	117.9 (3)

C30—C1—C2—N1	−114.0 (3)	C17—C18—C19—C6	−176.6 (3)
C4—C1—C2—N1	11.1 (3)	C9—C18—C19—C6	−56.4 (3)
C30—C1—C2—C36	122.1 (3)	C5—C6—C19—C18	−173.3 (2)
C4—C1—C2—C36	−112.8 (3)	C7—C6—C19—C18	61.6 (3)
C30—C1—C4—C5	−145.9 (3)	C39—C6—C19—C18	−62.3 (3)
C2—C1—C4—C5	89.5 (3)	C5—C6—C19—C20	−40.5 (3)
C30—C1—C4—C20	−27.4 (3)	C7—C6—C19—C20	−165.6 (2)
C2—C1—C4—C20	−151.9 (2)	C39—C6—C19—C20	70.4 (3)
C30—C1—C4—C3	96.3 (3)	C18—C19—C20—C4	170.4 (2)
C2—C1—C4—C3	−28.3 (3)	C6—C19—C20—C4	42.3 (3)
N1—C3—C4—C5	−78.9 (3)	C5—C4—C20—C19	−26.6 (3)
C21—C3—C4—C5	48.7 (3)	C1—C4—C20—C19	−147.7 (2)
N1—C3—C4—C20	164.5 (2)	C3—C4—C20—C19	94.4 (2)
C21—C3—C4—C20	−67.8 (3)	N1—C3—C21—C26	−139.7 (3)
N1—C3—C4—C1	36.9 (3)	C4—C3—C21—C26	97.2 (3)
C21—C3—C4—C1	164.6 (2)	N1—C3—C21—C22	45.1 (3)
C20—C4—C5—O1	−174.4 (3)	C4—C3—C21—C22	−78.0 (3)
C1—C4—C5—O1	−47.1 (4)	C26—C21—C22—C23	−1.1 (4)
C3—C4—C5—O1	64.0 (3)	C3—C21—C22—C23	174.0 (3)
C20—C4—C5—C6	1.6 (3)	C21—C22—C23—O5	−179.3 (3)
C1—C4—C5—C6	128.9 (2)	C21—C22—C23—C24	0.1 (4)
C3—C4—C5—C6	−120.0 (2)	O5—C23—C24—O6	−4.7 (4)
O1—C5—C6—C7	−41.2 (4)	C22—C23—C24—O6	175.8 (3)
C4—C5—C6—C7	142.9 (3)	O5—C23—C24—C25	179.2 (3)
O1—C5—C6—C19	−160.2 (3)	C22—C23—C24—C25	−0.3 (4)
C4—C5—C6—C19	23.9 (3)	O6—C24—C25—O7	5.0 (4)
O1—C5—C6—C39	82.0 (4)	C23—C24—C25—O7	−178.9 (3)
C4—C5—C6—C39	−93.9 (3)	O6—C24—C25—C26	−174.5 (3)
C5—C6—C7—C8	−173.0 (3)	C23—C24—C25—C26	1.6 (4)
C19—C6—C7—C8	−58.1 (3)	O7—C25—C26—C21	177.9 (3)
C39—C6—C7—C8	67.3 (3)	C24—C25—C26—C21	−2.6 (4)
C6—C7—C8—C9	54.4 (4)	C22—C21—C26—C25	2.4 (4)
C7—C8—C9—C10	−177.8 (3)	C3—C21—C26—C25	−172.9 (2)
C7—C8—C9—C18	−51.3 (4)	C2—C1—C30—C31	−139.2 (4)
C18—C9—C10—C11	−145.8 (3)	C4—C1—C30—C31	101.7 (4)
C8—C9—C10—C11	−17.4 (5)	C2—C1—C30—C35	42.2 (4)
C18—C9—C10—C15	33.1 (4)	C4—C1—C30—C35	−76.8 (4)
C8—C9—C10—C15	161.5 (3)	C35—C30—C31—C32	−1.0 (7)
C15—C10—C11—C12	3.8 (5)	C1—C30—C31—C32	−179.6 (5)
C9—C10—C11—C12	−177.2 (3)	C30—C31—C32—C33	0.2 (10)
C10—C11—C12—C13	−1.0 (5)	C31—C32—C33—C34	0.4 (11)
C11—C12—C13—O2	177.8 (3)	C32—C33—C34—C35	−0.3 (10)
C11—C12—C13—C14	−1.8 (6)	C33—C34—C35—C30	−0.4 (8)
O2—C13—C14—C15	−178.0 (4)	C31—C30—C35—C34	1.1 (6)
C12—C13—C14—C15	1.6 (6)	C1—C30—C35—C34	179.6 (4)
C13—C14—C15—C10	1.3 (7)	N1—C2—C36—O3	7.9 (4)
C13—C14—C15—C16	−176.3 (5)	C1—C2—C36—O3	131.0 (4)
C11—C10—C15—C14	−4.0 (6)	N1—C2—C36—O4	−176.0 (3)
C9—C10—C15—C14	177.0 (4)	C1—C2—C36—O4	−52.9 (4)
C11—C10—C15—C16	173.5 (5)	C36—C2—N1—C3	139.8 (2)
C9—C10—C15—C16	−5.5 (6)	C1—C2—N1—C3	12.5 (3)
C14—C15—C16—C17	−178.6 (5)	C21—C3—N1—C2	−160.0 (2)
C10—C15—C16—C17	3.8 (8)	C4—C3—N1—C2	−31.3 (3)
C15—C16—C17—C18	−31.5 (7)	O3—C36—O4—C37	1.3 (6)
C16—C17—C18—C19	−179.9 (4)	C2—C36—O4—C37	−174.8 (4)
C16—C17—C18—C9	59.5 (5)	C38—C37—O4—C36	176.6 (5)
C10—C9—C18—C19	179.6 (2)	C22—C23—O5—C27	0.2 (5)
C8—C9—C18—C19	50.7 (3)	C24—C23—O5—C27	−179.3 (3)
C10—C9—C18—C17	−57.6 (3)	C25—C24—O6—C28	−86.9 (4)
C8—C9—C18—C17	173.5 (3)	C23—C24—O6—C28	97.0 (4)
C17—C18—C19—C20	59.7 (4)	C24—C25—O7—C29	170.9 (3)
C9—C18—C19—C20	179.8 (2)	C26—C25—O7—C29	−9.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1ⁱ	0.82	1.99	2.782 (4)	163
C39—H39A···O3ⁱⁱ	0.96	2.56	3.378 (4)	144
C29—H29A···Cg1ⁱⁱⁱ	0.96	3.00	3.820 (4)	144
C1—H1···O4	0.98	2.54	2.901 (4)	101

Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x+1/2, y−1/2, −z+2; (iii) −x+1/2, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₃₉H₄₅NO₇
M_r	639.76
Crystal system, space group	Monoclinic, C2
Temperature (K)	293
a, b, c (Å)	26.1776 (6), 10.3379 (2), 13.6631 (3)
β (°)	91.125 (1)
V (Å³)	3696.82 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.30 × 0.25

Data collection
Diffractometer	Bruker KappaAPEXII diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.977, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	38566, 3462, 3186
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.132, 1.11
No. of reflections	3462
No. of parameters	425
No. of restraints	319
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.24

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1ⁱ	0.82	1.99	2.782 (4)	163
C39—H39A···O3ⁱⁱ	0.96	2.56	3.378 (4)	144
C29—H29A···Cg1ⁱⁱⁱ	0.96	3.00	3.820 (4)	144

Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x+1/2, y−1/2, −z+2; (iii) −x+1/2, y+1/2, −z+1.

Acknowledgements

ETSK thanks Professor M. N. Ponnuswamy and Professor D. Velmurugan, Department of Crystallography and Biophysics, University of Madras, India, for their guidance and valuable suggestions. ETSK also thanks SRM Management for their support.

References

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Volume 64| Part 11| November 2008| Pages o2219-o2220

doi:10.1107/S1600536808034582

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 3-hydr­­oxy-13-methyl-4′-phenyl-2′-(3,4,5-tri­meth­oxy­phen­yl)-6,7,8,9,11,12,13,14,15,16-deca­hydro­spiro­[cyclo­penta­[a]phenanthrene-16,3′-pyrrolidine]-5′-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 3-hydroxy-13-methyl-4′-phenyl-2′-(3,4,5-trimethoxyphenyl)-6,7,8,9,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-16,3′-pyrrolidine]-5′-carboxylate