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Acta Cryst. (2012). E68, o560-o561    [ doi:10.1107/S1600536812003169 ]

7'-(2,5-Dimethoxyphenyl)-1',3',5',6',7',7a'-hexahydrodispiro[indan-2,5'-pyrrolo[1,2-c][1,3]thiazole-6',2''-indan]-1,3,1''-trione

A. C. Wei, M. A. Ali, T. S. Choon, I. A. Razak and S. Arshad

Abstract top

In the title compound, C30H25NO5S, all the five-membered rings are in envelope conformations with the spiro and methylene C atoms as the flap atoms. Intramolecular C-H...O interactions stabilize the molecular structure and form S(6) and S(7) ring motifs. The mean plane through the hexahydropyrrolo[1,2-c]thiazole ring [r.m.s deviation of 0.0393 (1) Å] makes dihedral angles of 60.92 (5), 88.33 (4) and 84.12 (4)° with the terminal benzene ring and the mean planes of the mono and di-oxo substituted indan rings, respectively. Molecules are linked by intermolecular C-H...O interactions into a three-dimensional network. In addition, C-H...[pi] and [pi]-[pi] interactions [centroid-to-centroid distance = 3.4084 (8) Å] further stabilize the crystal structure.

Comment top

As part of our ongoing search for novel heterocyclic compounds with antitubercular activity (Wei, Ali, Choon et al., 2011; Wei, Ali, Ismail et al., 2011; Wei, Ali, Yoon et al., 2011) our group has synthesized the title compound as described below.

In the molecular structure (Fig. 1), all five-membered rings are in envelope conformation with puckering parameters (Cremer & Pople, 1975) Q = 0.3813 (11) Å and φ = 152.84 (18)° with atom C2 at the flap for the thiazolidine ring (S1/C1/N1/C3/C2), Q = 0.4536 (12) Å and φ = 296.92 (15)° with atom C5 at the flap for the pyrrolidine ring (N1/C3–C6), Q = 0.1467 (12) Å and φ = 357.9 (5)° with atom C5 at the flap for the cyclopentane ring (C5/C15/C16/C21/C22) and Q = 0.0816 (13) Å and φ= 1.5 (9)° with atom C6 at the flap for the cyclopentene ring (C6–C8/C13/C14). The intramolecular C2—H2A···O1, C4—H4A···O1 and C22—H22B···O2 hydrogen bonds (Table 1) stabilize the molecular structure and form S(6) and S(7) ring motifs (Bernstein et al., 1995). In addition, the mean plane through the hexahydropyrrolo[1,2-c]thiazole ring (S1/N1/C1–C6) makes dihedral angles of 60.92 (5), 88.33 (4) and 84.12 (4)° with the terminal benzene ring (C23–C28) and the mean plane of the two 2,3-dihydro-1H-indene rings (C5/C15–C22, C6–C14), respectively. The bond lengths and angles are within normal ranges and comparable to related structures (Wei, Ali, Choon et al., 2011; Wei, Ali, Ismail et al., 2011; Wei, Ali, Yoon et al., 2011).

The crystal packing is shown in Fig. 2. The molecules are linked by the intermolecular C11—H11A···O3, C20—H20A···O2, C1—H1A···O4 and C30—H30C···O1 interactions (Table 1) into three-dimensional network. In addition, the crystal structure is further stabilized by an intermolecular C2—H2B···Cg1 (Table 1) interactions (Cg1 is the centroid of the C16–C22 ring). π–π interactions are also observed with centroid to centroid distance Cg2···Cg3 = 3.4084 (8) Å [Cg2 and Cg3 are the centroids of the cyclopentane ring (C5/C15/C16/C21/C22) and cyclopentene ring (C6–C8/C13/C14), respectively].

Related literature top

For related structures, see: Wei, Ali, Choon et al. (2011); Wei, Ali, Ismail et al. (2011); Wei, Ali, Yoon et al. (2011). For ring conformations, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 2-(2,5-dimethoxybenzylidene)-2,3-dihydro-1H-indene (0.001 mol), ninhydrin (0.001 mol) and thiazolidine-4-carboxylic acid (0.002 mol) was dissolved in methanol (10 ml) and refluxed for 4 h. After completion of the reaction as evident from TLC, the mixture was poured into crushed ice. The precipitated solid was filtered, washed and recrystallized from petroleum ether–ethyl acetate mixture (1:1 v/v) to afford the title compound as yellow crystals.

Refinement top

All H atoms were positioned geometrically [C—H = 0.95 and 1.00 Å] and refined using a riding model with Uiso(H) = 1.2 or 1.5Ueq(C). A rotating group model was applied to the methyl groups. Four outliners were omitted from the final refinement, -4 4 6, -1 -3 1, -3 -6 2 and -4 4 7.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. Intramolecular hydrogen bonds are shown as dashed lines
[Figure 2] Fig. 2. The crystal packing of the title compound viewed along the b axis. The H atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.
3'-(2,5-dimethoxyphenyl)-1,1'',3,3',3'',3'a,4',6'-octahydrodispiro[indene- 2,1'-pyrrolo[1,2-c][1,3]thiazole-2',2''-indene]-1,1'',3-trione top
Crystal data top
C30H25NO5SZ = 2
Mr = 511.57F(000) = 536
Triclinic, P1Dx = 1.394 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0425 (4) ÅCell parameters from 9674 reflections
b = 11.1127 (5) Åθ = 2.3–30.7°
c = 13.3005 (6) ŵ = 0.18 mm−1
α = 68.016 (1)°T = 100 K
β = 84.588 (1)°Plate, yellow
γ = 79.735 (1)°0.36 × 0.19 × 0.10 mm
V = 1218.95 (9) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer		7546 independent reflections
Radiation source: fine-focus sealed tube6172 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
φ and ω scansθmax = 30.8°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −13→13
Tmin = 0.939, Tmax = 0.983k = −15→16
27399 measured reflectionsl = −19→19
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0547P)2 + 0.3649P]
where P = (Fo2 + 2Fc2)/3
7546 reflections(Δ/σ)max = 0.001
336 parametersΔρmax = 0.46 e Å−3
0 restraintsΔρmin = −0.34 e Å−3
Crystal data top
C30H25NO5Sγ = 79.735 (1)°
Mr = 511.57V = 1218.95 (9) Å3
Triclinic, P1Z = 2
a = 9.0425 (4) ÅMo Kα radiation
b = 11.1127 (5) ŵ = 0.18 mm−1
c = 13.3005 (6) ÅT = 100 K
α = 68.016 (1)°0.36 × 0.19 × 0.10 mm
β = 84.588 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		7546 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		6172 reflections with I > 2σ(I)
Tmin = 0.939, Tmax = 0.983Rint = 0.030
27399 measured reflectionsθmax = 30.8°
Refinement top
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.106Δρmax = 0.46 e Å−3
S = 1.03Δρmin = −0.34 e Å−3
7546 reflectionsAbsolute structure: ?
336 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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*/Ueq
S10.73773 (3)0.75887 (3)0.32247 (3)0.02242 (8)
O10.48652 (10)0.81440 (8)0.08968 (7)0.02018 (17)
O20.13926 (9)0.78758 (9)0.38401 (7)0.01972 (17)
O30.22209 (10)0.66773 (8)0.08718 (6)0.02009 (17)
O40.69120 (10)0.08851 (8)0.50375 (7)0.02352 (18)
O50.42757 (10)0.42066 (9)0.12125 (7)0.02060 (17)
N10.46129 (10)0.70280 (9)0.33292 (8)0.01505 (17)
C10.53549 (13)0.81258 (12)0.32540 (10)0.0197 (2)
H1A0.50580.83890.38870.024*
H1B0.50600.88900.25860.024*
C20.71655 (13)0.62872 (12)0.27699 (10)0.0188 (2)
H2A0.71430.66110.19690.023*
H2B0.80010.55460.30190.023*
C30.56602 (12)0.58616 (11)0.32835 (9)0.01487 (19)
H3A0.58210.51970.40340.018*
C40.48564 (12)0.53056 (11)0.26182 (8)0.01420 (19)
H4A0.51930.57180.18440.017*
C50.31662 (12)0.59219 (10)0.27073 (8)0.01339 (18)
C60.33703 (12)0.73236 (11)0.26064 (8)0.01379 (19)
C70.36942 (12)0.82428 (11)0.14128 (9)0.0156 (2)
C80.24279 (13)0.93367 (11)0.10817 (9)0.0165 (2)
C90.22010 (14)1.03660 (12)0.00841 (10)0.0206 (2)
H9A0.28871.0420−0.05120.025*
C100.09331 (15)1.13115 (12)−0.00065 (10)0.0229 (2)
H10A0.07471.2021−0.06790.028*
C11−0.00773 (14)1.12392 (12)0.08755 (10)0.0233 (2)
H11A−0.09371.18960.07890.028*
C120.01611 (13)1.02212 (12)0.18730 (10)0.0208 (2)
H12A−0.05141.01760.24740.025*
C130.14256 (13)0.92684 (11)0.19611 (9)0.0167 (2)
C140.19522 (12)0.81249 (11)0.29325 (9)0.01488 (19)
C150.22061 (12)0.59216 (11)0.18119 (8)0.01511 (19)
C160.12391 (12)0.49049 (11)0.23166 (9)0.01496 (19)
C170.03024 (13)0.44286 (12)0.18221 (9)0.0189 (2)
H17A0.02250.47610.10560.023*
C18−0.05095 (13)0.34581 (12)0.24801 (10)0.0209 (2)
H18A−0.11460.31120.21640.025*
C19−0.03949 (13)0.29862 (12)0.36080 (10)0.0196 (2)
H19A−0.09590.23220.40480.024*
C200.05276 (12)0.34686 (11)0.40993 (9)0.0169 (2)
H20A0.05910.31470.48660.020*
C210.13569 (12)0.44365 (11)0.34392 (9)0.01400 (19)
C220.24062 (12)0.51134 (11)0.37847 (8)0.01415 (19)
H22A0.31620.44650.42850.017*
H22B0.18430.56940.41480.017*
C230.52094 (12)0.38279 (11)0.29094 (9)0.01523 (19)
C240.58450 (12)0.29594 (11)0.38738 (9)0.0171 (2)
H24A0.59800.32750.44260.020*
C250.62912 (12)0.16255 (11)0.40491 (10)0.0183 (2)
C260.61226 (13)0.11484 (12)0.32496 (10)0.0211 (2)
H26A0.64670.02520.33550.025*
C270.54419 (14)0.19992 (12)0.22873 (10)0.0218 (2)
H27A0.53020.16750.17410.026*
C280.49688 (13)0.33129 (11)0.21227 (9)0.0175 (2)
C290.75456 (15)−0.04449 (12)0.52243 (12)0.0270 (3)
H29A0.7961−0.08530.59510.040*
H29B0.8348−0.04740.46810.040*
H29C0.6764−0.09230.51700.040*
C300.38015 (16)0.37160 (14)0.04664 (10)0.0272 (3)
H30A0.32360.4439−0.01090.041*
H30B0.31590.30500.08490.041*
H30C0.46840.33220.01470.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01879 (14)0.01845 (15)0.03543 (17)−0.00579 (10)−0.00349 (11)−0.01403 (12)
O10.0222 (4)0.0175 (4)0.0211 (4)−0.0063 (3)0.0074 (3)−0.0077 (3)
O20.0224 (4)0.0204 (4)0.0179 (4)−0.0058 (3)0.0050 (3)−0.0088 (3)
O30.0277 (4)0.0174 (4)0.0149 (4)−0.0050 (3)−0.0012 (3)−0.0048 (3)
O40.0283 (4)0.0122 (4)0.0293 (4)0.0013 (3)−0.0056 (3)−0.0076 (3)
O50.0279 (4)0.0197 (4)0.0188 (4)−0.0060 (3)−0.0003 (3)−0.0112 (3)
N10.0163 (4)0.0122 (4)0.0198 (4)−0.0047 (3)0.0002 (3)−0.0085 (3)
C10.0189 (5)0.0160 (5)0.0294 (6)−0.0068 (4)0.0015 (4)−0.0129 (5)
C20.0169 (5)0.0157 (5)0.0271 (5)−0.0047 (4)−0.0001 (4)−0.0108 (4)
C30.0174 (5)0.0113 (5)0.0178 (5)−0.0040 (4)−0.0007 (4)−0.0066 (4)
C40.0162 (5)0.0127 (5)0.0159 (4)−0.0053 (4)0.0019 (3)−0.0069 (4)
C50.0164 (4)0.0115 (5)0.0135 (4)−0.0050 (4)0.0010 (3)−0.0051 (4)
C60.0155 (4)0.0121 (5)0.0148 (4)−0.0040 (4)0.0022 (3)−0.0058 (4)
C70.0201 (5)0.0118 (5)0.0162 (5)−0.0057 (4)0.0028 (4)−0.0060 (4)
C80.0199 (5)0.0120 (5)0.0183 (5)−0.0048 (4)0.0016 (4)−0.0058 (4)
C90.0255 (6)0.0163 (5)0.0196 (5)−0.0075 (4)0.0022 (4)−0.0048 (4)
C100.0290 (6)0.0155 (5)0.0221 (5)−0.0043 (4)−0.0036 (4)−0.0033 (4)
C110.0256 (6)0.0179 (6)0.0263 (6)0.0006 (4)−0.0039 (5)−0.0089 (5)
C120.0216 (5)0.0193 (6)0.0226 (5)−0.0013 (4)0.0006 (4)−0.0099 (5)
C130.0190 (5)0.0135 (5)0.0188 (5)−0.0042 (4)0.0010 (4)−0.0068 (4)
C140.0164 (5)0.0136 (5)0.0173 (5)−0.0054 (4)0.0019 (4)−0.0078 (4)
C150.0178 (5)0.0137 (5)0.0153 (4)−0.0030 (4)0.0002 (4)−0.0068 (4)
C160.0155 (5)0.0143 (5)0.0168 (5)−0.0034 (4)0.0000 (4)−0.0071 (4)
C170.0184 (5)0.0213 (6)0.0205 (5)−0.0034 (4)−0.0018 (4)−0.0111 (4)
C180.0174 (5)0.0208 (6)0.0299 (6)−0.0051 (4)−0.0015 (4)−0.0143 (5)
C190.0161 (5)0.0136 (5)0.0294 (6)−0.0049 (4)0.0005 (4)−0.0073 (4)
C200.0160 (5)0.0134 (5)0.0202 (5)−0.0035 (4)−0.0001 (4)−0.0046 (4)
C210.0134 (4)0.0120 (5)0.0174 (5)−0.0028 (4)0.0003 (3)−0.0061 (4)
C220.0170 (5)0.0136 (5)0.0133 (4)−0.0062 (4)0.0002 (3)−0.0049 (4)
C230.0153 (4)0.0134 (5)0.0196 (5)−0.0051 (4)0.0031 (4)−0.0085 (4)
C240.0175 (5)0.0142 (5)0.0222 (5)−0.0045 (4)0.0012 (4)−0.0092 (4)
C250.0166 (5)0.0138 (5)0.0256 (5)−0.0042 (4)0.0014 (4)−0.0081 (4)
C260.0206 (5)0.0146 (5)0.0319 (6)−0.0050 (4)0.0030 (4)−0.0127 (5)
C270.0248 (6)0.0196 (6)0.0279 (6)−0.0067 (4)0.0030 (4)−0.0159 (5)
C280.0187 (5)0.0172 (5)0.0201 (5)−0.0059 (4)0.0025 (4)−0.0101 (4)
C290.0288 (6)0.0130 (6)0.0360 (7)0.0018 (5)−0.0007 (5)−0.0077 (5)
C300.0384 (7)0.0295 (7)0.0210 (5)−0.0110 (6)−0.0008 (5)−0.0149 (5)
Geometric parameters (Å, º) top
S1—C21.8083 (12)C11—C121.3891 (17)
S1—C11.8213 (12)C11—H11A0.9500
O1—C71.2174 (13)C12—C131.3939 (16)
O2—C141.2142 (13)C12—H12A0.9500
O3—C151.2180 (13)C13—C141.4771 (16)
O4—C251.3729 (14)C15—C161.4715 (15)
O4—C291.4229 (15)C16—C211.3928 (14)
O5—C281.3660 (14)C16—C171.3985 (15)
O5—C301.4264 (14)C17—C181.3864 (17)
N1—C61.4595 (14)C17—H17A0.9500
N1—C11.4617 (14)C18—C191.3990 (17)
N1—C31.4802 (14)C18—H18A0.9500
C1—H1A0.9900C19—C201.3909 (16)
C1—H1B0.9900C19—H19A0.9500
C2—C31.5347 (16)C20—C211.3951 (15)
C2—H2A0.9900C20—H20A0.9500
C2—H2B0.9900C21—C221.5075 (14)
C3—C41.5439 (14)C22—H22A0.9900
C3—H3A1.0000C22—H22B0.9900
C4—C231.5195 (15)C23—C241.3862 (16)
C4—C51.5724 (15)C23—C281.4162 (14)
C4—H4A1.0000C24—C251.4001 (16)
C5—C151.5387 (14)C24—H24A0.9500
C5—C221.5503 (15)C25—C261.3845 (16)
C5—C61.5555 (15)C26—C271.3951 (18)
C6—C141.5501 (15)C26—H26A0.9500
C6—C71.5666 (15)C27—C281.3848 (16)
C7—C81.4768 (15)C27—H27A0.9500
C8—C91.3937 (16)C29—H29A0.9800
C8—C131.3977 (15)C29—H29B0.9800
C9—C101.3910 (17)C29—H29C0.9800
C9—H9A0.9500C30—H30A0.9800
C10—C111.4039 (18)C30—H30B0.9800
C10—H10A0.9500C30—H30C0.9800
C2—S1—C192.41 (5)C8—C13—C14110.52 (10)
C25—O4—C29117.86 (10)O2—C14—C13125.67 (10)
C28—O5—C30117.49 (10)O2—C14—C6125.75 (10)
C6—N1—C1116.85 (9)C13—C14—C6108.55 (9)
C6—N1—C3109.94 (8)O3—C15—C16127.44 (10)
C1—N1—C3114.03 (9)O3—C15—C5124.96 (10)
N1—C1—S1107.80 (8)C16—C15—C5107.52 (9)
N1—C1—H1A110.1C21—C16—C17121.64 (10)
S1—C1—H1A110.1C21—C16—C15109.33 (9)
N1—C1—H1B110.1C17—C16—C15129.03 (10)
S1—C1—H1B110.1C18—C17—C16118.22 (10)
H1A—C1—H1B108.5C18—C17—H17A120.9
C3—C2—S1104.63 (7)C16—C17—H17A120.9
C3—C2—H2A110.8C17—C18—C19120.29 (10)
S1—C2—H2A110.8C17—C18—H18A119.9
C3—C2—H2B110.8C19—C18—H18A119.9
S1—C2—H2B110.8C20—C19—C18121.43 (11)
H2A—C2—H2B108.9C20—C19—H19A119.3
N1—C3—C2108.88 (9)C18—C19—H19A119.3
N1—C3—C4105.18 (8)C19—C20—C21118.44 (10)
C2—C3—C4113.74 (9)C19—C20—H20A120.8
N1—C3—H3A109.6C21—C20—H20A120.8
C2—C3—H3A109.6C16—C21—C20119.98 (10)
C4—C3—H3A109.6C16—C21—C22112.13 (9)
C23—C4—C3115.74 (9)C20—C21—C22127.88 (10)
C23—C4—C5117.58 (9)C21—C22—C5104.02 (8)
C3—C4—C5102.55 (8)C21—C22—H22A111.0
C23—C4—H4A106.7C5—C22—H22A111.0
C3—C4—H4A106.7C21—C22—H22B111.0
C5—C4—H4A106.7C5—C22—H22B111.0
C15—C5—C22104.83 (8)H22A—C22—H22B109.0
C15—C5—C6113.28 (9)C24—C23—C28117.81 (10)
C22—C5—C6115.15 (8)C24—C23—C4123.85 (9)
C15—C5—C4112.77 (8)C28—C23—C4118.21 (10)
C22—C5—C4111.13 (8)C23—C24—C25121.22 (10)
C6—C5—C499.96 (8)C23—C24—H24A119.4
N1—C6—C14112.51 (8)C25—C24—H24A119.4
N1—C6—C5101.36 (8)O4—C25—C26124.86 (11)
C14—C6—C5114.44 (9)O4—C25—C24114.81 (10)
N1—C6—C7113.84 (9)C26—C25—C24120.32 (11)
C14—C6—C7101.90 (8)C25—C26—C27119.25 (11)
C5—C6—C7113.32 (8)C25—C26—H26A120.4
O1—C7—C8125.97 (10)C27—C26—H26A120.4
O1—C7—C6125.21 (10)C28—C27—C26120.45 (10)
C8—C7—C6108.37 (9)C28—C27—H27A119.8
C9—C8—C13121.07 (11)C26—C27—H27A119.8
C9—C8—C7128.86 (10)O5—C28—C27124.19 (10)
C13—C8—C7109.99 (10)O5—C28—C23114.99 (10)
C10—C9—C8117.57 (11)C27—C28—C23120.81 (11)
C10—C9—H9A121.2O4—C29—H29A109.5
C8—C9—H9A121.2O4—C29—H29B109.5
C9—C10—C11121.34 (11)H29A—C29—H29B109.5
C9—C10—H10A119.3O4—C29—H29C109.5
C11—C10—H10A119.3H29A—C29—H29C109.5
C12—C11—C10120.99 (11)H29B—C29—H29C109.5
C12—C11—H11A119.5O5—C30—H30A109.5
C10—C11—H11A119.5O5—C30—H30B109.5
C11—C12—C13117.65 (11)H30A—C30—H30B109.5
C11—C12—H12A121.2O5—C30—H30C109.5
C13—C12—H12A121.2H30A—C30—H30C109.5
C12—C13—C8121.37 (11)H30B—C30—H30C109.5
C12—C13—C14128.06 (10)
C6—N1—C1—S1−134.10 (8)C8—C13—C14—O2173.06 (11)
C3—N1—C1—S1−3.99 (11)C12—C13—C14—C6177.49 (11)
C2—S1—C1—N121.48 (9)C8—C13—C14—C6−5.04 (12)
C1—S1—C2—C3−31.84 (8)N1—C6—C14—O2−48.10 (15)
C6—N1—C3—C2113.37 (10)C5—C6—C14—O266.90 (14)
C1—N1—C3—C2−20.09 (12)C7—C6—C14—O2−170.40 (11)
C6—N1—C3—C4−8.87 (11)N1—C6—C14—C13129.99 (9)
C1—N1—C3—C4−142.33 (9)C5—C6—C14—C13−115.01 (10)
S1—C2—C3—N134.39 (10)C7—C6—C14—C137.69 (11)
S1—C2—C3—C4151.30 (8)C22—C5—C15—O3162.88 (11)
N1—C3—C4—C23−149.38 (9)C6—C5—C15—O336.55 (15)
C2—C3—C4—C2391.57 (11)C4—C5—C15—O3−76.08 (14)
N1—C3—C4—C5−20.04 (10)C22—C5—C15—C16−14.21 (11)
C2—C3—C4—C5−139.09 (9)C6—C5—C15—C16−140.54 (9)
C23—C4—C5—C15−71.71 (12)C4—C5—C15—C16106.83 (10)
C3—C4—C5—C15160.10 (9)O3—C15—C16—C21−168.21 (11)
C23—C4—C5—C2245.66 (12)C5—C15—C16—C218.79 (12)
C3—C4—C5—C22−82.53 (10)O3—C15—C16—C1711.16 (19)
C23—C4—C5—C6167.69 (9)C5—C15—C16—C17−171.85 (11)
C3—C4—C5—C639.51 (9)C21—C16—C17—C18−0.56 (17)
C1—N1—C6—C14−71.05 (12)C15—C16—C17—C18−179.85 (11)
C3—N1—C6—C14156.95 (9)C16—C17—C18—C190.60 (17)
C1—N1—C6—C5166.27 (9)C17—C18—C19—C20−0.08 (18)
C3—N1—C6—C534.26 (10)C18—C19—C20—C21−0.51 (17)
C1—N1—C6—C744.24 (12)C17—C16—C21—C20−0.02 (16)
C3—N1—C6—C7−87.76 (11)C15—C16—C21—C20179.40 (10)
C15—C5—C6—N1−164.96 (8)C17—C16—C21—C22−178.82 (10)
C22—C5—C6—N174.39 (10)C15—C16—C21—C220.60 (12)
C4—C5—C6—N1−44.74 (9)C19—C20—C21—C160.55 (16)
C15—C5—C6—C1473.69 (11)C19—C20—C21—C22179.14 (10)
C22—C5—C6—C14−46.96 (12)C16—C21—C22—C5−9.50 (12)
C4—C5—C6—C14−166.09 (8)C20—C21—C22—C5171.82 (10)
C15—C5—C6—C7−42.58 (12)C15—C5—C22—C2113.99 (11)
C22—C5—C6—C7−163.23 (9)C6—C5—C22—C21139.16 (9)
C4—C5—C6—C777.64 (10)C4—C5—C22—C21−108.12 (9)
N1—C6—C7—O143.42 (15)C3—C4—C23—C2417.73 (15)
C14—C6—C7—O1164.81 (11)C5—C4—C23—C24−103.87 (12)
C5—C6—C7—O1−71.73 (14)C3—C4—C23—C28−157.93 (10)
N1—C6—C7—C8−129.22 (9)C5—C4—C23—C2880.47 (12)
C14—C6—C7—C8−7.83 (11)C28—C23—C24—C252.52 (16)
C5—C6—C7—C8115.62 (10)C4—C23—C24—C25−173.15 (10)
O1—C7—C8—C99.64 (19)C29—O4—C25—C265.59 (17)
C6—C7—C8—C9−177.79 (11)C29—O4—C25—C24−173.03 (11)
O1—C7—C8—C13−167.21 (11)C23—C24—C25—O4179.56 (10)
C6—C7—C8—C135.37 (12)C23—C24—C25—C260.87 (17)
C13—C8—C9—C10−0.76 (17)O4—C25—C26—C27178.59 (11)
C7—C8—C9—C10−177.30 (11)C24—C25—C26—C27−2.86 (18)
C8—C9—C10—C110.45 (18)C25—C26—C27—C281.39 (18)
C9—C10—C11—C120.35 (19)C30—O5—C28—C2710.24 (17)
C10—C11—C12—C13−0.82 (18)C30—O5—C28—C23−170.86 (10)
C11—C12—C13—C80.51 (17)C26—C27—C28—O5−179.08 (11)
C11—C12—C13—C14177.73 (11)C26—C27—C28—C232.08 (18)
C9—C8—C13—C120.29 (17)C24—C23—C28—O5177.07 (10)
C7—C8—C13—C12177.43 (10)C4—C23—C28—O5−7.01 (15)
C9—C8—C13—C14−177.38 (10)C24—C23—C28—C27−3.99 (16)
C7—C8—C13—C14−0.24 (13)C4—C23—C28—C27171.93 (10)
C12—C13—C14—O2−4.42 (19)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C16–C21 ring.
D—H···AD—HH···AD···AD—H···A
C2—H2A···O10.992.583.2234 (15)123
C4—H4A···O11.002.493.1289 (15)122
C22—H22B···O20.992.273.0697 (16)137
C11—H11A···O3i0.952.443.1210 (15)129
C20—H20A···O2ii0.952.483.1176 (14)124
C1—H1A···O4iii0.992.403.2806 (16)148
C30—H30C···O1iv0.982.473.2433 (18)136
C2—H2B···Cg1v0.992.583.5224 (14)160
Symmetry codes: (i) −x, −y+2, −z; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+1, −z; (v) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C16–C21 ring.
D—H···AD—HH···AD···AD—H···A
C2—H2A···O10.99002.58003.2234 (15)123.00
C4—H4A···O11.00002.49003.1289 (15)122.00
C22—H22B···O20.99002.27003.0697 (16)137.00
C11—H11A···O3i0.95002.44003.1210 (15)129.00
C20—H20A···O2ii0.95002.48003.1176 (14)124.00
C1—H1A···O4iii0.99002.40003.2806 (16)148.00
C30—H30C···O1iv0.98002.47003.2433 (18)136.00
C2—H2B···Cg1v0.99002.58003.5224 (14)160.00
Symmetry codes: (i) −x, −y+2, −z; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+1, −z; (v) x+1, y, z.
Acknowledgements top

The authors thank the Malaysian Goverment and Universiti Sains Malaysia for Research University grant No. 1001/PFIZIK/811151 and also for providing research facilities.

references
References top

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