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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2923.
Published online 2009 October 31. doi:  10.1107/S1600536809044547
PMCID: PMC2971326

3-Benzyl-9-phenyl-2-tosyl-2,3,3a,4,9,9a-hexa­hydro-1H-pyrrolo[3,4-b]quinoline

Abstract

In the title compound, C31H30N2O2S, the pyrrolidine ring adopts a twist conformation while the tetra­hydro­pyridine ring is in a half-chair conformation. The two rings are trans-fused. The pyridine-bound phenyl ring forms dihedral angles of 17.7 (1) and 48.1 (1)°, respectively, with the tosyl and benzyl phenyl rings. The mol­ecular structure is stabilized by an N—H(...)π inter­action involving the benzyl phenyl ring. In the crystal structure, mol­ecules translated by one unit along the a axis are linked into chains by C—H(...)π inter­actions involving the benzene ring of the tosyl group.

Related literature

For the biological activity of pyrroloquinoline derivatives, see: Ferlin et al. (2005 [triangle]); Dalla Via et al. (2008 [triangle]); Xiao et al. (2006 [triangle]); Fujita et al. (1996 [triangle]); Crenshaw et al. (1976 [triangle]). For the crystal structure of the 3-ethyl analogue, see: Sudha et al. (2008 [triangle]). For ring puckering parameters, see: Cremer & Pople (1975 [triangle]). For asymmetry parameters, see: Duax et al. (1976 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2923-scheme1.jpg

Experimental

Crystal data

  • C31H30N2O2S
  • M r = 494.63
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2923-efi1.jpg
  • a = 10.9521 (3) Å
  • b = 11.2563 (3) Å
  • c = 12.5132 (3) Å
  • α = 100.930 (2)°
  • β = 108.577 (1)°
  • γ = 114.539 (1)°
  • V = 1234.00 (6) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.16 mm−1
  • T = 100 K
  • 0.48 × 0.24 × 0.23 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.761, T max = 0.963
  • 27773 measured reflections
  • 6486 independent reflections
  • 5001 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.112
  • S = 1.01
  • 6486 reflections
  • 330 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.51 e Å−3
  • Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809044547/wn2361sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044547/wn2361Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

HKF thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

Pyrroloquinoline derivatives exhibit antitumor (Ferlin et al., 2005; Dalla Via et al., 2008), cytotoxic (Xiao et al., 2006), antibacterial (Fujita et al., 1996) and interferon-inducing activities (Crenshaw et al., 1976). As part of our studies on pyrroloquinoline derivatives, we report here the crystal structure of the title compound.

In the title molecule, the pyrrolidine ring adopts a twist conformation; the asymmetry parameter ΔC2[C2—C10] (Duax et al., 1976) and the puckering parameters q2 and [var phi] (Cremer & Pople, 1975) are 7.5 (2)°, 0.394 (2) Å and 96.5 (3)°, respectively. The tosyl group is attached to the pyrrolidine ring in an equatorial position. The tetrahydropyridine ring adopts a half-chair conformation, with Q, θ, [var phi] and ΔC2[C4—C9] values of 0.543 (2) Å, 131.1 (2)°, 93.1 (3)° and 6.6 (2)°, respectively. The phenyl group is attached to the tetrahydropyridine ring in a biaxial position. The C19—C24 phenyl ring forms dihedral angles of 74.0 (1) and 17.7 (1)°, respectively, with the C4—C9 and C12—C17 benzene rings. The C12—C17 and C26—C31 rings are oriented at a dihedral angle of 48.1 (1)°. The molecular structure is stabilized by an N—H···π interaction (Table 1, Fig. 1). Bond lengths and angles are comparable to those observed in the 3-ethyl analogue (Sudha et al., 2008).

In the crystal structure, molecules translated by one unit along the a axis are linked into chains by C—H···π interactions (Fig.2, Table 1) involving the benzene ring of the tosyl group.

Experimental

InCl3 (20 mol%) was added to a mixture of 2-(N-cinnamyl-N-tosylamino)-3-phenyl propanal (1 mmol) and aniline (1 mmol) in acetonitrile (20 ml). The reaction mixture was stirred at room temperature for 1 min. On completion of the reaction, as indicated by TLC, the mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine and dried over Na2SO4. The solvent was evaporated in vacuo and the crude product was chromatographed on silica gel using a hexane-ethyl acetate (8.5:1.5 v/v) mixture to obtain the title compound. The compound was recrystallized from ethyl acetate solution by slow evaporation.

Refinement

The N-bound H atom was located from a difference map and refined freely. The remaining H atoms were positioned geometrically (C—H = 0.93–0.98 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl). A rotating group model was used for the methyl groups.

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius. The dotted line indicates an N—H···π interaction. ...
Fig. 2.
Crystal packing of the title compound. C—H···π interactions are shown as dashed lines. For the sake of clarity, H atoms not involved in these interactions have been omitted.

Crystal data

C31H30N2O2SZ = 2
Mr = 494.63F(000) = 524
Triclinic, P1Dx = 1.331 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.9521 (3) ÅCell parameters from 9232 reflections
b = 11.2563 (3) Åθ = 2.3–30.0°
c = 12.5132 (3) ŵ = 0.16 mm1
α = 100.930 (2)°T = 100 K
β = 108.577 (1)°Block, colourless
γ = 114.539 (1)°0.48 × 0.24 × 0.23 mm
V = 1234.00 (6) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer6486 independent reflections
Radiation source: fine-focus sealed tube5001 reflections with I > 2σ(I)
graphiteRint = 0.040
[var phi] and ω scansθmax = 29.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −14→14
Tmin = 0.761, Tmax = 0.963k = −15→15
27773 measured reflectionsl = −17→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.046P)2 + 0.7475P] where P = (Fo2 + 2Fc2)/3
6486 reflections(Δ/σ)max = 0.001
330 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = −0.42 e Å3

Special details

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)

xyzUiso*/Ueq
S10.36310 (4)0.70596 (4)−0.01644 (4)0.01857 (10)
O10.25363 (13)0.74003 (13)−0.07610 (11)0.0250 (3)
O20.40078 (13)0.62325 (12)−0.08784 (10)0.0240 (3)
N10.51710 (14)0.85539 (13)0.07238 (12)0.0173 (3)
N20.87750 (15)1.02866 (14)0.33742 (12)0.0179 (3)
H1N20.939 (2)1.009 (2)0.3253 (18)0.026 (5)*
C10.50851 (17)0.96845 (16)0.14938 (14)0.0181 (3)
H1A0.41810.92920.16040.022*
H1B0.51091.03810.11360.022*
C20.64811 (17)1.03222 (15)0.26952 (14)0.0150 (3)
H20.62440.97700.31940.018*
C30.72246 (17)1.18825 (15)0.34620 (14)0.0151 (3)
H30.73431.24080.29250.018*
C40.87963 (17)1.23749 (16)0.44241 (14)0.0158 (3)
C50.95793 (18)1.36418 (16)0.54193 (15)0.0185 (3)
H50.91221.41670.54960.022*
C61.10111 (18)1.41433 (17)0.62954 (15)0.0210 (3)
H61.15091.49950.69450.025*
C71.16958 (18)1.33567 (17)0.61916 (15)0.0215 (3)
H71.26591.36830.67740.026*
C81.09513 (18)1.20931 (17)0.52270 (15)0.0194 (3)
H81.14141.15700.51690.023*
C90.95044 (17)1.15885 (16)0.43336 (14)0.0165 (3)
C100.75726 (17)1.00918 (16)0.23056 (14)0.0156 (3)
H100.79821.07790.19540.019*
C110.66205 (17)0.86091 (16)0.13260 (14)0.0171 (3)
H110.64870.79060.17030.021*
C120.30055 (17)0.61554 (16)0.07342 (14)0.0183 (3)
C130.35945 (18)0.53371 (16)0.11236 (15)0.0207 (3)
H130.43320.52910.09330.025*
C140.30604 (19)0.45969 (17)0.17978 (15)0.0218 (3)
H140.34520.40570.20600.026*
C150.19503 (18)0.46425 (16)0.20920 (15)0.0202 (3)
C160.13799 (18)0.54575 (17)0.16856 (15)0.0217 (3)
H160.06320.54920.18660.026*
C170.19011 (18)0.62183 (16)0.10184 (15)0.0208 (3)
H170.15150.67650.07640.025*
C180.1399 (2)0.38679 (18)0.28517 (17)0.0254 (4)
H18A0.03550.35530.25930.038*
H18B0.19580.44870.36910.038*
H18C0.15330.30700.27550.038*
C190.63082 (17)1.21998 (16)0.40329 (14)0.0164 (3)
C200.61254 (18)1.17490 (17)0.49677 (15)0.0205 (3)
H200.65251.12060.52110.025*
C210.53582 (19)1.20987 (18)0.55365 (16)0.0254 (4)
H210.52501.17960.61600.031*
C220.47489 (19)1.29029 (18)0.51758 (17)0.0270 (4)
H220.42271.31340.55530.032*
C230.49216 (19)1.33563 (18)0.42575 (16)0.0248 (4)
H230.45231.39020.40210.030*
C240.56895 (18)1.30027 (16)0.36793 (15)0.0200 (3)
H240.57891.33050.30540.024*
C250.72722 (18)0.83906 (18)0.04379 (15)0.0213 (3)
H25A0.66720.7416−0.01200.026*
H25B0.72350.8977−0.00340.026*
C260.88731 (18)0.87601 (17)0.11140 (14)0.0193 (3)
C271.00564 (19)1.00373 (17)0.12935 (15)0.0219 (3)
H270.98551.06330.09420.026*
C281.1526 (2)1.04302 (18)0.19876 (16)0.0251 (4)
H281.23041.12720.20770.030*
C291.18447 (19)0.95779 (19)0.25491 (16)0.0262 (4)
H291.28330.98530.30300.031*
C301.0679 (2)0.83100 (19)0.23886 (17)0.0259 (4)
H301.08860.77390.27730.031*
C310.92062 (19)0.78886 (17)0.16586 (16)0.0226 (4)
H310.84340.70190.15310.027*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.01624 (19)0.01639 (19)0.01461 (19)0.00506 (15)0.00412 (15)0.00178 (14)
O10.0177 (6)0.0274 (6)0.0207 (6)0.0083 (5)0.0026 (5)0.0090 (5)
O20.0232 (6)0.0204 (6)0.0171 (6)0.0060 (5)0.0082 (5)−0.0016 (5)
N10.0150 (6)0.0137 (6)0.0176 (7)0.0066 (5)0.0048 (5)0.0009 (5)
N20.0174 (7)0.0189 (7)0.0163 (7)0.0124 (6)0.0047 (5)0.0017 (5)
C10.0167 (7)0.0165 (7)0.0197 (8)0.0095 (6)0.0072 (6)0.0033 (6)
C20.0156 (7)0.0141 (7)0.0158 (7)0.0083 (6)0.0074 (6)0.0043 (6)
C30.0156 (7)0.0134 (7)0.0160 (7)0.0076 (6)0.0070 (6)0.0042 (6)
C40.0149 (7)0.0154 (7)0.0166 (7)0.0069 (6)0.0077 (6)0.0053 (6)
C50.0200 (8)0.0152 (7)0.0207 (8)0.0091 (6)0.0106 (6)0.0046 (6)
C60.0179 (8)0.0163 (7)0.0188 (8)0.0042 (6)0.0062 (6)0.0012 (6)
C70.0146 (7)0.0235 (8)0.0186 (8)0.0064 (6)0.0052 (6)0.0042 (7)
C80.0178 (8)0.0227 (8)0.0206 (8)0.0129 (7)0.0088 (6)0.0074 (7)
C90.0172 (7)0.0164 (7)0.0158 (7)0.0081 (6)0.0085 (6)0.0048 (6)
C100.0157 (7)0.0144 (7)0.0154 (7)0.0078 (6)0.0064 (6)0.0035 (6)
C110.0153 (7)0.0154 (7)0.0164 (7)0.0074 (6)0.0049 (6)0.0022 (6)
C120.0179 (8)0.0135 (7)0.0148 (7)0.0045 (6)0.0047 (6)0.0011 (6)
C130.0203 (8)0.0175 (7)0.0209 (8)0.0094 (7)0.0091 (7)0.0016 (6)
C140.0270 (9)0.0176 (7)0.0226 (8)0.0135 (7)0.0112 (7)0.0055 (6)
C150.0212 (8)0.0136 (7)0.0184 (8)0.0059 (6)0.0071 (6)0.0013 (6)
C160.0182 (8)0.0198 (8)0.0246 (9)0.0089 (7)0.0097 (7)0.0052 (7)
C170.0182 (8)0.0163 (7)0.0229 (8)0.0082 (6)0.0063 (7)0.0042 (6)
C180.0301 (9)0.0217 (8)0.0292 (9)0.0142 (7)0.0165 (8)0.0109 (7)
C190.0138 (7)0.0133 (7)0.0163 (7)0.0050 (6)0.0056 (6)0.0012 (6)
C200.0201 (8)0.0176 (7)0.0220 (8)0.0088 (6)0.0096 (7)0.0058 (6)
C210.0212 (8)0.0238 (8)0.0224 (9)0.0050 (7)0.0119 (7)0.0029 (7)
C220.0177 (8)0.0249 (9)0.0282 (9)0.0077 (7)0.0109 (7)−0.0037 (7)
C230.0201 (8)0.0224 (8)0.0289 (9)0.0138 (7)0.0081 (7)0.0016 (7)
C240.0185 (8)0.0165 (7)0.0203 (8)0.0086 (6)0.0062 (6)0.0030 (6)
C250.0215 (8)0.0218 (8)0.0173 (8)0.0116 (7)0.0073 (7)0.0018 (6)
C260.0212 (8)0.0201 (8)0.0157 (7)0.0120 (7)0.0090 (6)0.0002 (6)
C270.0253 (8)0.0210 (8)0.0200 (8)0.0126 (7)0.0113 (7)0.0053 (7)
C280.0229 (8)0.0221 (8)0.0231 (9)0.0070 (7)0.0118 (7)0.0024 (7)
C290.0191 (8)0.0304 (9)0.0229 (9)0.0123 (7)0.0075 (7)0.0019 (7)
C300.0296 (9)0.0260 (9)0.0277 (9)0.0198 (8)0.0124 (8)0.0082 (7)
C310.0243 (8)0.0183 (8)0.0245 (9)0.0114 (7)0.0124 (7)0.0030 (7)

Geometric parameters (Å, °)

S1—O11.4360 (12)C14—C151.395 (2)
S1—O21.4401 (12)C14—H140.93
S1—N11.6277 (13)C15—C161.393 (2)
S1—C121.7649 (17)C15—C181.507 (2)
N1—C111.4934 (19)C16—C171.387 (2)
N1—C11.4996 (19)C16—H160.93
N2—C91.406 (2)C17—H170.93
N2—C101.448 (2)C18—H18A0.96
N2—H1N20.83 (2)C18—H18B0.96
C1—C21.526 (2)C18—H18C0.96
C1—H1A0.97C19—C241.393 (2)
C1—H1B0.97C19—C201.399 (2)
C2—C101.521 (2)C20—C211.385 (2)
C2—C31.531 (2)C20—H200.93
C2—H20.98C21—C221.390 (3)
C3—C191.518 (2)C21—H210.93
C3—C41.534 (2)C22—C231.377 (3)
C3—H30.98C22—H220.93
C4—C51.397 (2)C23—C241.395 (2)
C4—C91.409 (2)C23—H230.93
C5—C61.384 (2)C24—H240.93
C5—H50.93C25—C261.510 (2)
C6—C71.390 (2)C25—H25A0.97
C6—H60.93C25—H25B0.97
C7—C81.380 (2)C26—C271.393 (2)
C7—H70.93C26—C311.397 (2)
C8—C91.402 (2)C27—C281.383 (2)
C8—H80.93C27—H270.93
C10—C111.530 (2)C28—C291.383 (3)
C10—H100.98C28—H280.93
C11—C251.534 (2)C29—C301.386 (3)
C11—H110.98C29—H290.93
C12—C171.389 (2)C30—C311.387 (2)
C12—C131.402 (2)C30—H300.93
C13—C141.387 (2)C31—H310.93
C13—H130.93
O1—S1—O2119.68 (7)C14—C13—C12118.98 (15)
O1—S1—N1106.27 (7)C14—C13—H13120.5
O2—S1—N1106.96 (7)C12—C13—H13120.5
O1—S1—C12107.58 (8)C13—C14—C15121.68 (15)
O2—S1—C12107.09 (7)C13—C14—H14119.2
N1—S1—C12108.93 (7)C15—C14—H14119.2
C11—N1—C1111.99 (12)C16—C15—C14118.02 (16)
C11—N1—S1120.85 (10)C16—C15—C18120.34 (15)
C1—N1—S1118.57 (10)C14—C15—C18121.62 (15)
C9—N2—C10114.33 (12)C17—C16—C15121.59 (16)
C9—N2—H1N2111.4 (14)C17—C16—H16119.2
C10—N2—H1N2116.0 (14)C15—C16—H16119.2
N1—C1—C2103.14 (12)C16—C17—C12119.40 (15)
N1—C1—H1A111.1C16—C17—H17120.3
C2—C1—H1A111.1C12—C17—H17120.3
N1—C1—H1B111.1C15—C18—H18A109.5
C2—C1—H1B111.1C15—C18—H18B109.5
H1A—C1—H1B109.1H18A—C18—H18B109.5
C10—C2—C1103.00 (12)C15—C18—H18C109.5
C10—C2—C3109.13 (12)H18A—C18—H18C109.5
C1—C2—C3118.14 (13)H18B—C18—H18C109.5
C10—C2—H2108.7C24—C19—C20118.41 (15)
C1—C2—H2108.7C24—C19—C3120.85 (14)
C3—C2—H2108.7C20—C19—C3120.67 (14)
C19—C3—C2113.47 (12)C21—C20—C19120.97 (16)
C19—C3—C4111.61 (12)C21—C20—H20119.5
C2—C3—C4108.54 (12)C19—C20—H20119.5
C19—C3—H3107.7C20—C21—C22120.01 (17)
C2—C3—H3107.7C20—C21—H21120.0
C4—C3—H3107.7C22—C21—H21120.0
C5—C4—C9117.86 (14)C23—C22—C21119.69 (16)
C5—C4—C3120.29 (13)C23—C22—H22120.2
C9—C4—C3121.85 (13)C21—C22—H22120.2
C6—C5—C4122.35 (15)C22—C23—C24120.49 (16)
C6—C5—H5118.8C22—C23—H23119.8
C4—C5—H5118.8C24—C23—H23119.8
C5—C6—C7119.10 (15)C19—C24—C23120.42 (16)
C5—C6—H6120.4C19—C24—H24119.8
C7—C6—H6120.4C23—C24—H24119.8
C8—C7—C6120.19 (15)C26—C25—C11110.75 (13)
C8—C7—H7119.9C26—C25—H25A109.5
C6—C7—H7119.9C11—C25—H25A109.5
C7—C8—C9120.77 (15)C26—C25—H25B109.5
C7—C8—H8119.6C11—C25—H25B109.5
C9—C8—H8119.6H25A—C25—H25B108.1
C8—C9—N2119.04 (14)C27—C26—C31118.39 (15)
C8—C9—C4119.73 (14)C27—C26—C25120.46 (15)
N2—C9—C4121.22 (14)C31—C26—C25120.94 (15)
N2—C10—C2107.97 (13)C28—C27—C26120.86 (16)
N2—C10—C11115.04 (12)C28—C27—H27119.6
C2—C10—C11104.70 (12)C26—C27—H27119.6
N2—C10—H10109.6C27—C28—C29120.38 (16)
C2—C10—H10109.6C27—C28—H28119.8
C11—C10—H10109.6C29—C28—H28119.8
N1—C11—C10100.91 (11)C28—C29—C30119.44 (16)
N1—C11—C25112.14 (13)C28—C29—H29120.3
C10—C11—C25113.02 (13)C30—C29—H29120.3
N1—C11—H11110.2C29—C30—C31120.37 (17)
C10—C11—H11110.2C29—C30—H30119.8
C25—C11—H11110.2C31—C30—H30119.8
C17—C12—C13120.33 (15)C30—C31—C26120.50 (16)
C17—C12—S1120.10 (13)C30—C31—H31119.8
C13—C12—S1119.54 (13)C26—C31—H31119.8
O1—S1—N1—C11−169.30 (12)N2—C10—C11—C25−86.66 (17)
O2—S1—N1—C11−40.37 (14)C2—C10—C11—C25155.01 (13)
C12—S1—N1—C1175.06 (13)O1—S1—C12—C17−16.92 (15)
O1—S1—N1—C145.43 (13)O2—S1—C12—C17−146.77 (13)
O2—S1—N1—C1174.35 (12)N1—S1—C12—C1797.88 (14)
C12—S1—N1—C1−70.22 (13)O1—S1—C12—C13160.95 (12)
C11—N1—C1—C2−7.78 (16)O2—S1—C12—C1331.10 (14)
S1—N1—C1—C2140.39 (11)N1—S1—C12—C13−84.25 (13)
N1—C1—C2—C1029.34 (15)C17—C12—C13—C14−0.2 (2)
N1—C1—C2—C3149.66 (13)S1—C12—C13—C14−178.03 (12)
C10—C2—C3—C19−172.66 (13)C12—C13—C14—C150.3 (2)
C1—C2—C3—C1970.25 (18)C13—C14—C15—C160.1 (2)
C10—C2—C3—C4−47.97 (16)C13—C14—C15—C18−178.40 (15)
C1—C2—C3—C4−165.07 (13)C14—C15—C16—C17−0.7 (2)
C19—C3—C4—C5−38.87 (19)C18—C15—C16—C17177.88 (15)
C2—C3—C4—C5−164.65 (14)C15—C16—C17—C120.8 (2)
C19—C3—C4—C9141.90 (15)C13—C12—C17—C16−0.4 (2)
C2—C3—C4—C916.12 (19)S1—C12—C17—C16177.50 (12)
C9—C4—C5—C60.7 (2)C2—C3—C19—C24−113.47 (16)
C3—C4—C5—C6−178.57 (15)C4—C3—C19—C24123.52 (15)
C4—C5—C6—C7−0.5 (3)C2—C3—C19—C2069.60 (18)
C5—C6—C7—C8−0.1 (3)C4—C3—C19—C20−53.42 (18)
C6—C7—C8—C90.6 (3)C24—C19—C20—C21−0.5 (2)
C7—C8—C9—N2−179.10 (15)C3—C19—C20—C21176.54 (14)
C7—C8—C9—C4−0.4 (2)C19—C20—C21—C220.4 (2)
C10—N2—C9—C8−159.03 (14)C20—C21—C22—C23−0.4 (3)
C10—N2—C9—C422.3 (2)C21—C22—C23—C240.6 (3)
C5—C4—C9—C8−0.2 (2)C20—C19—C24—C230.7 (2)
C3—C4—C9—C8179.05 (14)C3—C19—C24—C23−176.33 (14)
C5—C4—C9—N2178.46 (15)C22—C23—C24—C19−0.8 (2)
C3—C4—C9—N2−2.3 (2)N1—C11—C25—C26167.76 (13)
C9—N2—C10—C2−55.04 (17)C10—C11—C25—C2654.52 (18)
C9—N2—C10—C11−171.53 (13)C11—C25—C26—C27−102.25 (18)
C1—C2—C10—N2−164.09 (12)C11—C25—C26—C3172.43 (19)
C3—C2—C10—N269.58 (15)C31—C26—C27—C280.4 (2)
C1—C2—C10—C11−41.05 (15)C25—C26—C27—C28175.20 (15)
C3—C2—C10—C11−167.38 (12)C26—C27—C28—C29−2.0 (3)
C1—N1—C11—C10−16.78 (16)C27—C28—C29—C301.4 (3)
S1—N1—C11—C10−164.12 (11)C28—C29—C30—C310.9 (3)
C1—N1—C11—C25−137.32 (14)C29—C30—C31—C26−2.5 (3)
S1—N1—C11—C2575.33 (16)C27—C26—C31—C301.9 (2)
N2—C10—C11—N1153.42 (13)C25—C26—C31—C30−172.91 (15)
C2—C10—C11—N135.09 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H1N2···Cg20.83 (2)2.61 (2)3.374 (2)152 (2)
C29—H29···Cg1i0.932.903.605 (2)134

Symmetry codes: (i) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2361).

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