Diethyl 1-benzyl-2,2-dioxo-4-phenyl-3,4,6,7,8,8a-hexa­hydro-1H-pyrrolo­[2,1-c][1,4]thia­zine-1,3-dicarboxyl­ate

Chitradevi, A.; Athimoolam, S.; Bahadur, S.A.; Indumathi, S.; Perumal, S.

doi:10.1107/S1600536811031047

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2268

doi:10.1107/S1600536811031047

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Diethyl 1-benzyl-2,2-dioxo-4-phenyl-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[2,1-c][1,4]thiazine-1,3-dicarboxylate

A. Chitradevi,^a S. Athimoolam,^b ^* S. Asath Bahadur,^c S. Indumathi ^d and S. Perumal ^d

^aDepartment of Physics, Sri Subramanya College of Engineering & Technology, Palani 624 615, India, ^bDepartment of Physics, University College of Engineering Nagercoil, Anna University of Technology Tirunelveli, Nagercoil 629 004, India, ^cDepartment of Physics, Kalasalingam University, Krishnan koil 626 190, India, and ^dDepartment of Organic Chemistry, Madurai Kamaraj University, Madurai 625 021, India
^*Correspondence e-mail: athi81s@yahoo.co.in

(Received 16 May 2011; accepted 2 August 2011; online 6 August 2011)

In the title compound, C₂₆H₃₁NO₆S, the five-membered pyrrolidine ring adopts an envelope conformation and the six-membered thiazine ring is in a distorted chair conformation. The crystal packing is stabilized through an intermolecular C—H⋯O interaction, generating inversion-related R₂²(10) ring motifs.

Related literature

For the biological and pharmacological importance of thiazine compounds, see: Moriyama et al. (2004 ); Koketsu et al. (2002 ). For the biological and pharmacological properties of compounds containing the pyrrolidine sub-structure, see: Hemming & Patel (2004 ); Kueh et al. (2003 ). For biological properties of compounds containing the pyrrolothiazine scaffold, see: Armenise et al. (1991 , 1998 ). For ring puckering analysis, see: Cremer & Pople (1975 ). For hydrogen-bonding interactions, see: Desiraju & Steiner (1999 ). For graph-set analysis, see: Etter et al. (1990 ).

Experimental

Crystal data

C₂₆H₃₁NO₆S
M_r = 485.58
Monoclinic, P 2₁ /c
a = 13.5232 (9) Å
b = 16.8402 (12) Å
c = 12.1789 (9) Å
β = 116.568 (1)°
V = 2480.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 293 K
0.22 × 0.18 × 0.15 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
23528 measured reflections
4360 independent reflections
3885 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.112
S = 1.05
4360 reflections
328 parameters
H-atom parameters constrained
Δρ_max = 0.34 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
C5—H5⋯O11ⁱ	0.98	2.51	3.447 (2)	159
Symmetry code: (i) -x, -y+2, -z+1.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811031047/su2277sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031047/su2277Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811031047/su2277Isup3.cml

checkCIF report

Comment top

Thiazines occupy a unique place in medicinal chemistry since they show diverse biological properties, such as antifungal, anti-inflammatory, anti-HIV, anti-psoriatic, sedative, neuroleptic, antitussive and anti-tubercular (Moriyama et al., 2004; Koketsu et al., 2002). In addition, compounds with a pyrrolidine sub-structure exhibit anti-tumour, analgesic, antidepressant, antihistaminic, anti-asthmatic and anti-Parkinson activities (Hemming & Patel, 2004; Kueh et al., 2003). Compounds containing the pyrrolothiazine scaffold have also been shown to exhibit anti-inflammatory, anti-fungal and anti-microbial activities (Armenise et al., 1998; Armenise et al., 1991).

The molecular structure of the title molecule is illustrated in Fig. 1. The five-membered pyrrolidine ring has an envelope conformation [puckering parameters: Q(2) = 0.412 (2) Å, ϕ(2) = 152.9 (3)°; Cremer & Pople, 1975], with atom C6 at the flap. The six-membered thazine ring adopts a slightly distorted chair conformation [Puckering parameters: Q(2) = 0.1011 (19) Å, ϕ(2) = 101.2 (9) ° and Q(3) = 0.6610 (17) Å]. The dihedral angle between the phenyl rings is 54.3 (1)°. The planes of the carboxylate groups (CO₂) are oriented with a dihedral angle of 22.5 (3)°.

In the crystal molecules are linked via intermolecular C—H···O interactions (Desiraju & Steiner, 1999). This interaction makes a R₂²(10) ring motif centered about an inversion center (Table 1, Fig. 2; Etter et al., 1990).

Related literature top

For the biological and pharmacological importance of thiazine compounds, see: Moriyama et al. (2004); Koketsu et al. (2002). For the biological and pharmacological properties of compounds containing the pyrrolidine sub-structure, see: Hemming & Patel (2004); Kueh et al. (2003). For biological properties of compounds containing the pyrrolothiazine scaffold, see: Armenise et al. (1991, 1998). For ring puckering analysis, see: Cremer & Pople (1975). For hydrogen-bonding interactions, see: Desiraju & Steiner (1999). For graph-set analysis, see: Etter et al. (1990).

Experimental top

A mixture of ethyl 2-[(2-ethoxy-2-oxoethyl)sulfonyl]acetate (1.6 mmol), benzaldehyde (3.2 mmol) and pyrrolidine (1.6 mmol) was dissolved in ethanol (10 ml), heated until the solution turned yellow and stirred at room temperature for 2–5 days. After completion of the reaction, the crude product was purified using flash column chromatography on silica gel (230–400 mesh) with petroleum ether and ethyl acetate mixture (95:5 v/v) as an eluent. Crystals, suitable for X-ray diffraction analysis, were obtained by recrystallization from ethanol.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule with atom numbering scheme and 30% probability displacement ellipsoids. H-bonds are shown as dashed lines.
	Fig. 2. Packing diagram of the title compound viewed down the b-axis. H-bonds are shown as dashed lines (see Table 1 for details).

Diethyl 1-benzyl-2,2-dioxo-4-phenyl-3,4,6,7,8,8a-hexahydro-1H- pyrrolo[2,1-c][1,4]thiazine-1,3-dicarboxylate top

Crystal data top

C₂₆H₃₁NO₆S	F(000) = 1032
M_r = 485.58	D_x = 1.300 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 419 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.5232 (9) Å	Cell parameters from 3512 reflections
b = 16.8402 (12) Å	θ = 2.4–23.8°
c = 12.1789 (9) Å	µ = 0.17 mm⁻¹
β = 116.568 (1)°	T = 293 K
V = 2480.7 (3) Å³	Block, colourless
Z = 4	0.22 × 0.18 × 0.15 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3885 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 25.0°, θ_min = 1.7°
ω scans	h = −15→16
23528 measured reflections	k = −19→19
4360 independent 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0573P)² + 0.6606P] where P = (F_o² + 2F_c²)/3
4360 reflections	(Δ/σ)_max = 0.001
328 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₆H₃₁NO₆S	V = 2480.7 (3) Å³
M_r = 485.58	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.5232 (9) Å	µ = 0.17 mm⁻¹
b = 16.8402 (12) Å	T = 293 K
c = 12.1789 (9) Å	0.22 × 0.18 × 0.15 mm
β = 116.568 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3885 reflections with I > 2σ(I)
23528 measured reflections	R_int = 0.023
4360 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.05	Δρ_max = 0.34 e Å⁻³
4360 reflections	Δρ_min = −0.21 e Å⁻³
328 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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)
S1	0.15741 (3)	0.92139 (2)	0.43420 (4)	0.0492 (1)
O3A	0.35985 (10)	0.97564 (9)	0.43234 (14)	0.0719 (5)
O3B	0.29527 (10)	1.07744 (8)	0.30412 (13)	0.0659 (5)
O4A	0.15678 (12)	0.88688 (9)	0.70359 (14)	0.0746 (5)
O4B	0.31214 (10)	0.83490 (7)	0.71181 (12)	0.0603 (4)
O11	0.04484 (10)	0.91684 (8)	0.41508 (13)	0.0635 (5)
O12	0.20400 (11)	0.85244 (7)	0.40719 (12)	0.0621 (4)
N1	0.22020 (11)	1.09127 (8)	0.53463 (13)	0.0514 (4)
C3B1	0.4011 (11)	1.0955 (8)	0.3087 (12)	0.091 (4)	0.600
C2	0.13365 (14)	1.07966 (10)	0.40838 (16)	0.0518 (5)
C3C1	0.4416 (7)	1.1711 (6)	0.3650 (10)	0.177 (5)	0.600
C3	0.16594 (12)	1.00898 (9)	0.34934 (15)	0.0475 (5)
C3A	0.28510 (13)	1.01706 (10)	0.36781 (16)	0.0505 (5)
C4	0.24346 (13)	0.94980 (9)	0.59187 (15)	0.0476 (5)
C4A	0.23023 (14)	0.88740 (10)	0.67482 (16)	0.0524 (5)
C4B	0.30779 (17)	0.77085 (12)	0.79068 (19)	0.0686 (7)
C4C	0.3898 (2)	0.71084 (15)	0.7988 (3)	0.0970 (10)
C5	0.21555 (13)	1.03327 (10)	0.62232 (16)	0.0505 (5)
C6	0.20688 (18)	1.17373 (11)	0.5649 (2)	0.0677 (7)
C7	0.19111 (19)	1.21696 (11)	0.4504 (2)	0.0739 (7)
C8	0.11953 (17)	1.16161 (11)	0.34662 (19)	0.0662 (7)
C31	0.07930 (13)	1.00024 (11)	0.21296 (16)	0.0562 (6)
C32	0.09916 (13)	0.93866 (10)	0.13463 (16)	0.0524 (5)
C33	0.16040 (15)	0.95665 (12)	0.07280 (17)	0.0624 (6)
C34	0.17452 (18)	0.90259 (14)	−0.00374 (19)	0.0717 (8)
C35	0.12652 (19)	0.82867 (13)	−0.02086 (19)	0.0738 (7)
C36	0.0654 (2)	0.80987 (13)	0.0397 (2)	0.0793 (8)
C37	0.05118 (16)	0.86437 (12)	0.11638 (19)	0.0683 (7)
C51	0.29799 (15)	1.05548 (10)	0.75148 (17)	0.0546 (6)
C52	0.2635 (2)	1.06714 (12)	0.8413 (2)	0.0710 (8)
C53	0.3373 (2)	1.08980 (14)	0.9581 (2)	0.0883 (10)
C54	0.4456 (2)	1.10084 (14)	0.9869 (2)	0.0895 (9)
C55	0.48211 (19)	1.09012 (14)	0.8991 (2)	0.0857 (9)
C56	0.40837 (16)	1.06721 (12)	0.7808 (2)	0.0683 (7)
C3B2	0.4149 (13)	1.0937 (6)	0.3395 (18)	0.062 (4)	0.400
C3C2	0.4129 (7)	1.1751 (5)	0.2913 (6)	0.069 (3)	0.400
H3B2	0.39440	1.09570	0.22600	0.1100*	0.600
H3C4	0.39340	1.21230	0.31500	0.2650*	0.600
H4	0.32070	0.94970	0.60600	0.0570*
H3C5	0.51470	1.17950	0.37260	0.2650*	0.600
H5	0.14100	1.03280	0.61670	0.0610*
H3C6	0.44390	1.17220	0.44490	0.2650*	0.600
H6A	0.27210	1.19240	0.63570	0.0810*
H6B	0.14290	1.17950	0.58040	0.0810*
H7A	0.26160	1.22640	0.44960	0.0890*
H7B	0.15430	1.26740	0.44380	0.0890*
H8A	0.14450	1.16030	0.28330	0.0790*
H8B	0.04280	1.17830	0.31020	0.0790*
H4B1	0.23440	0.74760	0.75600	0.0820*
H4B2	0.32490	0.79120	0.87170	0.0820*
H4C1	0.37360	0.69250	0.71780	0.1450*
H4C2	0.38700	0.66690	0.84750	0.1450*
H4C3	0.46240	0.73390	0.83620	0.1450*
H31A	0.00850	0.98860	0.21160	0.0670*
H31B	0.07240	1.05140	0.17370	0.0670*
H33	0.19290	1.00650	0.08310	0.0750*
H34	0.21660	0.91600	−0.04400	0.0860*
H35	0.13550	0.79200	−0.07280	0.0890*
H36	0.03310	0.75990	0.02910	0.0950*
H37	0.00880	0.85080	0.15620	0.0820*
H52	0.18960	1.05960	0.82260	0.0850*
H53	0.31280	1.09760	1.01750	0.1060*
H54	0.49520	1.11570	1.06620	0.1070*
H55	0.55620	1.09820	0.91880	0.1030*
H56	0.43310	1.05980	0.72150	0.0820*
H3B1	0.45370	1.05450	0.35490	0.1100*	0.600
H2	0.06460	1.06630	0.41180	0.0620*
H3B3	0.45890	1.09190	0.42780	0.0740*	0.400
H3B4	0.44420	1.05570	0.30180	0.0740*	0.400
H3C1	0.36030	1.17710	0.20620	0.1030*	0.400
H3C2	0.48500	1.18830	0.29970	0.1030*	0.400
H3C3	0.39210	1.21240	0.33690	0.1030*	0.400

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0454 (2)	0.0417 (2)	0.0580 (3)	−0.0019 (2)	0.0209 (2)	−0.0040 (2)
O3A	0.0435 (7)	0.0786 (9)	0.0905 (10)	0.0157 (6)	0.0273 (7)	0.0259 (8)
O3B	0.0477 (7)	0.0663 (8)	0.0768 (9)	−0.0028 (6)	0.0218 (6)	0.0149 (7)
O4A	0.0731 (9)	0.0739 (9)	0.0948 (10)	0.0031 (7)	0.0537 (8)	0.0090 (8)
O4B	0.0588 (7)	0.0533 (7)	0.0682 (8)	0.0028 (6)	0.0279 (6)	0.0108 (6)
O11	0.0481 (7)	0.0620 (8)	0.0773 (9)	−0.0112 (6)	0.0252 (6)	−0.0060 (6)
O12	0.0750 (8)	0.0440 (6)	0.0674 (8)	0.0058 (6)	0.0320 (7)	−0.0032 (6)
N1	0.0450 (7)	0.0401 (7)	0.0608 (8)	0.0022 (6)	0.0163 (6)	−0.0026 (6)
C3B1	0.059 (5)	0.136 (8)	0.073 (5)	−0.009 (4)	0.024 (4)	0.012 (4)
C2	0.0408 (8)	0.0450 (9)	0.0628 (10)	0.0054 (7)	0.0172 (8)	0.0000 (7)
C3C1	0.087 (5)	0.147 (7)	0.299 (13)	−0.048 (5)	0.089 (8)	−0.088 (9)
C3	0.0389 (8)	0.0423 (8)	0.0561 (10)	0.0023 (6)	0.0165 (7)	0.0012 (7)
C3A	0.0429 (9)	0.0500 (9)	0.0533 (9)	0.0002 (7)	0.0169 (7)	0.0006 (7)
C4	0.0411 (8)	0.0438 (9)	0.0560 (9)	−0.0004 (7)	0.0200 (7)	−0.0023 (7)
C4A	0.0516 (9)	0.0478 (9)	0.0575 (10)	−0.0047 (7)	0.0241 (8)	−0.0052 (8)
C4B	0.0715 (12)	0.0615 (12)	0.0663 (12)	−0.0063 (10)	0.0249 (10)	0.0130 (9)
C4C	0.1060 (19)	0.0645 (14)	0.119 (2)	0.0164 (13)	0.0489 (16)	0.0299 (14)
C5	0.0422 (8)	0.0453 (9)	0.0622 (10)	0.0011 (7)	0.0218 (8)	−0.0054 (7)
C6	0.0679 (12)	0.0431 (10)	0.0787 (13)	0.0041 (8)	0.0207 (10)	−0.0070 (9)
C7	0.0739 (13)	0.0438 (10)	0.0942 (15)	0.0042 (9)	0.0289 (11)	0.0022 (10)
C8	0.0622 (11)	0.0486 (10)	0.0777 (13)	0.0125 (8)	0.0224 (10)	0.0064 (9)
C31	0.0405 (9)	0.0590 (10)	0.0583 (10)	0.0040 (7)	0.0124 (8)	0.0015 (8)
C32	0.0403 (8)	0.0545 (10)	0.0495 (9)	0.0000 (7)	0.0085 (7)	0.0015 (7)
C33	0.0599 (11)	0.0599 (11)	0.0597 (11)	−0.0040 (9)	0.0199 (9)	0.0026 (9)
C34	0.0684 (13)	0.0833 (15)	0.0618 (12)	0.0042 (11)	0.0278 (10)	0.0008 (11)
C35	0.0768 (14)	0.0715 (13)	0.0579 (11)	0.0145 (11)	0.0165 (10)	−0.0062 (10)
C36	0.0844 (15)	0.0594 (12)	0.0753 (14)	−0.0124 (11)	0.0190 (12)	−0.0104 (10)
C37	0.0623 (11)	0.0684 (12)	0.0673 (12)	−0.0166 (10)	0.0228 (10)	−0.0087 (10)
C51	0.0536 (10)	0.0427 (9)	0.0619 (11)	0.0002 (7)	0.0208 (8)	−0.0037 (8)
C52	0.0789 (14)	0.0624 (12)	0.0734 (13)	−0.0089 (10)	0.0355 (11)	−0.0122 (10)
C53	0.118 (2)	0.0741 (15)	0.0689 (14)	−0.0171 (14)	0.0382 (14)	−0.0137 (11)
C54	0.109 (2)	0.0680 (14)	0.0611 (13)	−0.0189 (13)	0.0109 (13)	−0.0026 (11)
C55	0.0618 (13)	0.0702 (14)	0.0918 (17)	−0.0102 (10)	0.0045 (12)	0.0033 (12)
C56	0.0539 (11)	0.0655 (12)	0.0722 (13)	−0.0026 (9)	0.0164 (9)	−0.0039 (10)
C3B2	0.036 (4)	0.050 (4)	0.089 (9)	−0.003 (3)	0.018 (5)	0.030 (4)
C3C2	0.074 (5)	0.054 (4)	0.083 (4)	−0.019 (3)	0.040 (4)	0.014 (3)

Geometric parameters (Å, º) top

S1—O11	1.4354 (16)	C55—C56	1.391 (3)
S1—O12	1.4279 (14)	C3B1—H3B1	0.9700
S1—C3	1.8341 (16)	C3B1—H3B2	0.9700
S1—C4	1.8087 (17)	C2—H2	0.9800
O3A—C3A	1.190 (2)	C3C1—H3C4	0.9600
O3B—C3B1	1.440 (16)	C3C1—H3C5	0.9600
O3B—C3A	1.323 (2)	C3C1—H3C6	0.9600
O3B—C3B2	1.50 (2)	C3B2—H3B3	0.9700
O4A—C4A	1.192 (3)	C3B2—H3B4	0.9700
O4B—C4A	1.329 (2)	C4—H4	0.9800
O4B—C4B	1.463 (2)	C3C2—H3C1	0.9600
N1—C2	1.471 (2)	C3C2—H3C3	0.9600
N1—C5	1.469 (2)	C3C2—H3C2	0.9600
N1—C6	1.468 (2)	C4B—H4B2	0.9700
C3B1—C3C1	1.434 (17)	C4B—H4B1	0.9700
C2—C3	1.551 (2)	C4C—H4C2	0.9600
C2—C8	1.542 (3)	C4C—H4C3	0.9600
C3—C3A	1.530 (3)	C4C—H4C1	0.9600
C3—C31	1.553 (2)	C5—H5	0.9800
C3B2—C3C2	1.487 (15)	C6—H6B	0.9700
C4—C4A	1.523 (2)	C6—H6A	0.9700
C4—C5	1.543 (2)	C7—H7A	0.9700
C4B—C4C	1.471 (4)	C7—H7B	0.9700
C5—C51	1.513 (3)	C8—H8A	0.9700
C6—C7	1.501 (3)	C8—H8B	0.9700
C7—C8	1.520 (3)	C31—H31B	0.9700
C31—C32	1.512 (3)	C31—H31A	0.9700
C32—C33	1.379 (3)	C33—H33	0.9300
C32—C37	1.381 (3)	C34—H34	0.9300
C33—C34	1.376 (3)	C35—H35	0.9300
C34—C35	1.376 (3)	C36—H36	0.9300
C35—C36	1.369 (4)	C37—H37	0.9300
C36—C37	1.383 (3)	C52—H52	0.9300
C51—C56	1.385 (3)	C53—H53	0.9300
C51—C52	1.382 (3)	C54—H54	0.9300
C52—C53	1.377 (3)	C55—H55	0.9300
C53—C54	1.358 (4)	C56—H56	0.9300
C54—C55	1.376 (4)

O11—S1—O12	117.67 (9)	H3C5—C3C1—H3C6	110.00
O11—S1—C3	106.32 (8)	H3B3—C3B2—H3B4	109.00
O11—S1—C4	108.57 (9)	O3B—C3B2—H3B3	111.00
O12—S1—C3	112.26 (8)	O3B—C3B2—H3B4	111.00
O12—S1—C4	108.60 (8)	C3C2—C3B2—H3B3	111.00
C3—S1—C4	102.28 (7)	C3C2—C3B2—H3B4	111.00
C3B1—O3B—C3A	120.1 (5)	C5—C4—H4	108.00
C3B2—O3B—C3A	110.7 (6)	C4A—C4—H4	108.00
C4A—O4B—C4B	116.17 (16)	S1—C4—H4	108.00
C2—N1—C5	113.51 (14)	H3C1—C3C2—H3C3	110.00
C2—N1—C6	104.99 (14)	C3B2—C3C2—H3C1	109.00
C5—N1—C6	113.35 (15)	C3B2—C3C2—H3C2	109.00
O3B—C3B1—C3C1	111.5 (11)	H3C2—C3C2—H3C3	109.00
N1—C2—C3	109.23 (15)	H3C1—C3C2—H3C2	109.00
N1—C2—C8	104.95 (14)	C3B2—C3C2—H3C3	109.00
C3—C2—C8	117.37 (16)	C4C—C4B—H4B2	110.00
S1—C3—C2	104.73 (11)	H4B1—C4B—H4B2	109.00
S1—C3—C3A	108.43 (11)	C4C—C4B—H4B1	110.00
S1—C3—C31	108.60 (11)	O4B—C4B—H4B1	110.00
C2—C3—C3A	111.10 (14)	O4B—C4B—H4B2	110.00
C2—C3—C31	109.53 (14)	C4B—C4C—H4C2	110.00
C3A—C3—C31	114.00 (14)	C4B—C4C—H4C3	110.00
O3B—C3B2—C3C2	103.2 (11)	C4B—C4C—H4C1	109.00
O3A—C3A—O3B	123.89 (19)	H4C2—C4C—H4C3	109.00
O3A—C3A—C3	124.94 (16)	H4C1—C4C—H4C2	109.00
O3B—C3A—C3	111.16 (15)	H4C1—C4C—H4C3	109.00
S1—C4—C5	112.69 (12)	N1—C5—H5	109.00
C4A—C4—C5	110.81 (15)	C4—C5—H5	109.00
S1—C4—C4A	108.13 (11)	C51—C5—H5	109.00
O4A—C4A—O4B	124.99 (17)	N1—C6—H6A	111.00
O4A—C4A—C4	124.11 (17)	H6A—C6—H6B	109.00
O4B—C4A—C4	110.90 (17)	N1—C6—H6B	111.00
O4B—C4B—C4C	107.5 (2)	C7—C6—H6A	111.00
N1—C5—C4	109.65 (14)	C7—C6—H6B	111.00
C4—C5—C51	109.23 (14)	C6—C7—H7B	111.00
N1—C5—C51	109.89 (14)	C8—C7—H7A	111.00
N1—C6—C7	101.99 (16)	C8—C7—H7B	111.00
C6—C7—C8	104.37 (17)	C6—C7—H7A	111.00
C2—C8—C7	104.44 (16)	H7A—C7—H7B	109.00
C3—C31—C32	118.54 (15)	C2—C8—H8B	111.00
C31—C32—C33	120.88 (16)	C7—C8—H8A	111.00
C33—C32—C37	117.70 (18)	H8A—C8—H8B	109.00
C31—C32—C37	121.31 (18)	C7—C8—H8B	111.00
C32—C33—C34	121.6 (2)	C2—C8—H8A	111.00
C33—C34—C35	120.2 (2)	C3—C31—H31A	108.00
C34—C35—C36	119.0 (2)	H31A—C31—H31B	107.00
C35—C36—C37	120.7 (2)	C32—C31—H31B	108.00
C32—C37—C36	120.9 (2)	C3—C31—H31B	108.00
C5—C51—C52	120.4 (2)	C32—C31—H31A	108.00
C52—C51—C56	118.83 (19)	C34—C33—H33	119.00
C5—C51—C56	120.76 (18)	C32—C33—H33	119.00
C51—C52—C53	120.8 (3)	C35—C34—H34	120.00
C52—C53—C54	120.3 (2)	C33—C34—H34	120.00
C53—C54—C55	120.1 (2)	C34—C35—H35	120.00
C54—C55—C56	120.1 (2)	C36—C35—H35	120.00
C51—C56—C55	119.8 (2)	C37—C36—H36	120.00
O3B—C3B1—H3B1	109.00	C35—C36—H36	120.00
O3B—C3B1—H3B2	109.00	C32—C37—H37	120.00
C3C1—C3B1—H3B1	109.00	C36—C37—H37	120.00
C3C1—C3B1—H3B2	109.00	C51—C52—H52	120.00
H3B1—C3B1—H3B2	108.00	C53—C52—H52	120.00
N1—C2—H2	108.00	C52—C53—H53	120.00
C3—C2—H2	108.00	C54—C53—H53	120.00
C8—C2—H2	108.00	C55—C54—H54	120.00
C3B1—C3C1—H3C4	109.00	C53—C54—H54	120.00
C3B1—C3C1—H3C5	109.00	C56—C55—H55	120.00
C3B1—C3C1—H3C6	110.00	C54—C55—H55	120.00
H3C4—C3C1—H3C5	109.00	C51—C56—H56	120.00
H3C4—C3C1—H3C6	110.00	C55—C56—H56	120.00

O11—S1—C3—C2	60.76 (13)	S1—C3—C3A—O3B	177.24 (12)
O11—S1—C3—C3A	179.45 (11)	C2—C3—C3A—O3A	110.7 (2)
O11—S1—C3—C31	−56.19 (14)	C2—C3—C3A—O3B	−68.19 (18)
O12—S1—C3—C2	−169.24 (12)	C31—C3—C3A—O3A	−125.01 (19)
O12—S1—C3—C3A	−50.56 (13)	C31—C3—C3A—O3B	56.15 (19)
O12—S1—C3—C31	73.80 (14)	S1—C3—C31—C32	−70.74 (18)
C4—S1—C3—C2	−53.02 (13)	C2—C3—C31—C32	175.43 (15)
C4—S1—C3—C3A	65.66 (13)	C3A—C3—C31—C32	50.3 (2)
C4—S1—C3—C31	−169.97 (12)	S1—C4—C4A—O4A	−83.5 (2)
O11—S1—C4—C4A	59.37 (14)	S1—C4—C4A—O4B	97.50 (15)
O11—S1—C4—C5	−63.46 (14)	C5—C4—C4A—O4A	40.5 (2)
O12—S1—C4—C4A	−69.69 (15)	C5—C4—C4A—O4B	−138.54 (15)
O12—S1—C4—C5	167.49 (13)	S1—C4—C5—N1	−54.12 (18)
C3—S1—C4—C4A	171.48 (13)	S1—C4—C5—C51	−174.60 (13)
C3—S1—C4—C5	48.66 (15)	C4A—C4—C5—N1	−175.43 (15)
C3A—O3B—C3B1—C3C1	−114.7 (9)	C4A—C4—C5—C51	64.1 (2)
C3B1—O3B—C3A—O3A	1.1 (7)	N1—C5—C51—C52	123.55 (18)
C3B1—O3B—C3A—C3	180.0 (6)	N1—C5—C51—C56	−54.2 (2)
C4B—O4B—C4A—O4A	2.0 (3)	C4—C5—C51—C52	−116.12 (19)
C4B—O4B—C4A—C4	−179.00 (14)	C4—C5—C51—C56	66.2 (2)
C4A—O4B—C4B—C4C	167.85 (18)	N1—C6—C7—C8	39.0 (2)
C5—N1—C2—C3	−77.18 (19)	C6—C7—C8—C2	−19.6 (2)
C5—N1—C2—C8	156.15 (16)	C3—C31—C32—C33	−87.6 (2)
C6—N1—C2—C3	158.50 (16)	C3—C31—C32—C37	96.5 (2)
C6—N1—C2—C8	31.8 (2)	C31—C32—C33—C34	−176.65 (19)
C2—N1—C5—C4	66.77 (19)	C37—C32—C33—C34	−0.6 (3)
C2—N1—C5—C51	−173.16 (15)	C31—C32—C37—C36	176.75 (19)
C6—N1—C5—C4	−173.57 (16)	C33—C32—C37—C36	0.7 (3)
C6—N1—C5—C51	−53.5 (2)	C32—C33—C34—C35	0.4 (3)
C2—N1—C6—C7	−44.3 (2)	C33—C34—C35—C36	−0.3 (3)
C5—N1—C6—C7	−168.71 (17)	C34—C35—C36—C37	0.5 (4)
N1—C2—C3—S1	67.82 (16)	C35—C36—C37—C32	−0.7 (3)
N1—C2—C3—C3A	−49.04 (18)	C5—C51—C52—C53	−177.94 (18)
N1—C2—C3—C31	−175.88 (14)	C56—C51—C52—C53	−0.2 (3)
C8—C2—C3—S1	−172.95 (15)	C5—C51—C56—C55	177.91 (18)
C8—C2—C3—C3A	70.2 (2)	C52—C51—C56—C55	0.2 (3)
C8—C2—C3—C31	−56.7 (2)	C51—C52—C53—C54	−0.2 (3)
N1—C2—C8—C7	−7.0 (2)	C52—C53—C54—C55	0.6 (4)
C3—C2—C8—C7	−128.48 (19)	C53—C54—C55—C56	−0.6 (4)
S1—C3—C3A—O3A	−3.9 (2)	C54—C55—C56—C51	0.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O11ⁱ	0.98	2.51	3.447 (2)	159

Symmetry code: (i) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₆H₃₁NO₆S
M_r	485.58
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.5232 (9), 16.8402 (12), 12.1789 (9)
β (°)	116.568 (1)
V (Å³)	2480.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.22 × 0.18 × 0.15

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	23528, 4360, 3885
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.112, 1.05
No. of reflections	4360
No. of parameters	328
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.21

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL/PC (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O11ⁱ	0.98	2.51	3.447 (2)	159

Symmetry code: (i) −x, −y+2, −z+1.

Acknowledgements

AC and SAB sincerely thank the Vice-Chancellor and Management of Kalasalingam University, Anand Nagar, Krishnan Koil, for their support and encouragement.

References

Armenise, D., Trapani, G., Arrivo, V. & Morlacchi, F. (1991). Farmaco, 46, 1023–1032. PubMed CAS Web of Science Google Scholar
Armenise, D., Trapani, G., Stasi, F. & Morlacchi, F. (1998). Arch. Pharm. 331, 54–58. CrossRef CAS Google Scholar
Bruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology. New York: Oxford University Press Inc. Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hemming, K. & Patel, N. (2004). Tetrahedron Lett. 45, 7553–7556. Web of Science CrossRef CAS Google Scholar
Koketsu, M., Tanaka, K., Takenaka, Y., Kwong, C. D. & Ishihara, H. (2002). Eur. J. Pharm. Sci. 15, 307–310. Web of Science CrossRef PubMed CAS Google Scholar
Kueh, A. J., Marriott, P. J., Wynne, P. M. & Vine, J. H. (2003). J. Chromatogr. A, 1000, 109–124. Web of Science CrossRef PubMed CAS Google Scholar
Moriyama, H., Tsukida, T., Inoue, Y., Yokota, K., Yoshino, K., Kondo, H., Miura, N. & Nishimura, S. (2004). J. Med. Chem. 47, 1930–1938. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 9| September 2011| Page o2268

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

Di­ethyl 1-benzyl-2,2-dioxo-4-phenyl-3,4,6,7,8,8a-hexa­hydro-1H-pyrrolo­[2,1-c][1,4]thia­zine-1,3-di­carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Diethyl 1-benzyl-2,2-dioxo-4-phenyl-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[2,1-c][1,4]thiazine-1,3-dicarboxylate