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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o2098.
Published online 2010 July 24. doi:  10.1107/S1600536810028746
PMCID: PMC3007469

Methyl 4-(4-chloro­phen­yl)-3,3a,4,4a,5,12c-hexa­hydro-2-thia­naphtho­[1′,2′:3,2]furo[5,4-b]pyrrolizine-4a-carboxyl­ate

Abstract

In the title compound, C25H22ClNO3S, both the pyrrolidinyl and thia­zolyl rings adopt envelope conformations whereas the dihydro­pyran ring adopts a half-chair conformation. The chloro­phenyl and naphthalenyl ring systems are oriented at a dihedral angle of 59.7 (1)°. The crystal packing is stabilized by an intra­molecular C—H(...)N hydrogen bond and weak inter­molecular C—H(...)π inter­actions.

Related literature

For related structures, see: Nirmala et al. (2009 [triangle]); Selvanayagam et al. (2010 [triangle]). For the superposition of related structures, see: Gans & Shalloway (2001 [triangle]). For ring-puckering and asymmetry parameters, see: Cremer & Pople (1975 [triangle]); Nardelli (1983 [triangle]).

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Object name is e-66-o2098-scheme1.jpg

Experimental

Crystal data

  • C25H22ClNO3S
  • M r = 451.95
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2098-efi1.jpg
  • a = 8.0740 (6) Å
  • b = 12.1109 (8) Å
  • c = 22.1813 (15) Å
  • V = 2169.0 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.30 mm−1
  • T = 292 K
  • 0.23 × 0.21 × 0.19 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • 25236 measured reflections
  • 5157 independent reflections
  • 4559 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.110
  • S = 1.04
  • 5157 reflections
  • 281 parameters
  • H-atom parameters constrained
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.15 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2186 Friedel pairs
  • Flack parameter: 0.01 (6)

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810028746/ng5001sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028746/ng5001Isup2.hkl

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

Acknowledgments

SS acknowledges the Department of Science and Technology (DST), India, for providing computing facilities under the DST-Fast Track Scheme. SS also thanks the Vice Chancellor and management of Kalasalingam University, Krishnankoil, for their support and encouragement.

supplementary crystallographic information

Comment

In continuation of our work on the crystal structure analysis of pyrrolizine derivatives, we have undertaken a single-crystal X-ray diffraction study for the title compound, and the results are presented here.

The X-ray study confirmed the molecular structure and atomic connectivity for (I), as illustrated in Fig. 1. A l l the bond lengths are normal and comparable to the standard values. Fig. 2 shows a superposition of the pyrrolidine ring of (I) with the related reported structures of Nirmala et al. (2009) and Selvanayagam et al. (2010), using Qmol (Gans & Shalloway, 2001); the r.m.s. deviation is 0.350 and 0.864 Å, respectively. The sum of the angles (331.9°) around atom N1 is in accordance with sp3 hybridization.

The chlorine atom deviates 0.118 (1) Å from the best plane of chlorophenyl ring. The naphthalene ring system (C2–C11) and the chlorophenyl ring are oriented with a dihedral angle of 59.7 (1)°. In the thiapyrrolizine ring system, both the pyrrolidine and thiazole rings N1/C1/C13–C15 and N1/C15/C16/S1/C17 adopt envelope conformations; the puckering parameters (Cremer & Pople, 1975) are: q2 = 0.447 (2) Å and [var phi] = -118.7 (2)° for N1/C1/C13–C15 ring, and q2 = 0.508 (2) Å and [var phi] = -59.9 (2)° for N1/C15/C16/S1/C17 ring. In the N1/C1/C13–C15 ring, atom C13 deviates by -0.675 (2) Å from the least-squares plane through the remaining four atoms, whereas in the ring N1/C15/C16/S1/C17, atom S1 deviates by -0.855 (1) Å from the plane through the remaining four atoms. The dihydropyran ring of the chromene unit adopts a half-chair conformation, with the lowest asymmetry parameter ΔC2(C2–C11) of 0.039 (1)° (Nardelli, 1983).

In addition to van der Waals interactions, the molecular packing is stabilized by intramolecular C—H···N hydrogen bond and intermolecular weak C—H···π interactions (Fig. 3).

Experimental

A mixture of (Z)-methyl-2[(1-formylnaphthalen-2-yloxy)methyl]-3-(4-chlorophenyl) acrylate (20 mmol) and thiaproline (30 mmol) was refluxed in benzene for 20 h and the solvent was removed under reduced pressure. The crude product was subjected to column chromatography to get the pure product. Single crystals were grown by slow evapoartion of a chloroform-methanol (1:1) soution.

Refinement

H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C—H = 0.93, 0.98, 0.97 and 0.96 Å for aromatic, methine, methylene and methyl H respectively, and Uiso(H) = 1.5Ueq(C) for methyl H and Uiso(H) = 1.2Ueq(C) for all other H atoms.

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level
Fig. 2.
Superposition of (I) (cyan) with the similar reported structures of Nirmala et al. (2009) (yellow) and Selvanayagam et al. (2010).
Fig. 3.
Molecular packing of the title compound, viewed along the b axis.

Crystal data

C25H22ClNO3SF(000) = 944
Mr = 451.95Dx = 1.384 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 16148 reflections
a = 8.0740 (6) Åθ = 2.1–27.6°
b = 12.1109 (8) ŵ = 0.30 mm1
c = 22.1813 (15) ÅT = 292 K
V = 2169.0 (3) Å3Block, colourless
Z = 40.23 × 0.21 × 0.19 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer4559 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
graphiteθmax = 28.1°, θmin = 1.8°
ω scansh = −10→10
25236 measured reflectionsk = −15→16
5157 independent reflectionsl = −29→29

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.110w = 1/[σ2(Fo2) + (0.0624P)2 + 0.2403P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
5157 reflectionsΔρmax = 0.28 e Å3
281 parametersΔρmin = −0.15 e Å3
0 restraintsAbsolute structure: Flack (1983), 2186 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.01 (6)

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
Cl1−0.39547 (9)0.77136 (7)0.50917 (3)0.0888 (2)
S1−0.28910 (8)1.01078 (6)0.12895 (3)0.07732 (19)
O10.2032 (2)0.67004 (11)0.21872 (8)0.0728 (5)
O20.2227 (2)0.98332 (12)0.25861 (7)0.0698 (4)
O30.21864 (19)0.84359 (14)0.32261 (7)0.0693 (4)
N1−0.13547 (18)0.82523 (13)0.15571 (7)0.0510 (4)
C10.03210 (19)0.86266 (14)0.17424 (8)0.0409 (3)
H10.04060.94290.16970.049*
C20.1710 (2)0.80726 (14)0.14034 (9)0.0479 (4)
C30.2357 (2)0.85149 (16)0.08546 (9)0.0514 (4)
C40.1812 (3)0.95119 (18)0.05993 (8)0.0586 (5)
H40.10060.99210.07990.070*
C50.2432 (3)0.9901 (3)0.00649 (10)0.0750 (6)
H50.20451.0563−0.00940.090*
C60.3656 (3)0.9295 (3)−0.02419 (11)0.0887 (9)
H60.40550.9545−0.06110.106*
C70.4251 (3)0.8353 (3)−0.00020 (12)0.0814 (8)
H70.50820.7971−0.02040.098*
C80.3646 (3)0.79322 (19)0.05482 (11)0.0647 (6)
C90.4312 (3)0.6989 (2)0.08106 (14)0.0822 (8)
H90.51460.66060.06110.099*
C100.3768 (3)0.66178 (18)0.13531 (15)0.0802 (7)
H100.42700.60100.15320.096*
C110.2438 (2)0.71561 (15)0.16450 (11)0.0596 (5)
C120.0538 (3)0.70803 (15)0.24674 (11)0.0570 (5)
H12A0.05510.68820.28910.068*
H12B−0.04050.67200.22810.068*
C130.0355 (2)0.83233 (13)0.24070 (8)0.0401 (3)
C14−0.1375 (2)0.87464 (13)0.26073 (8)0.0416 (3)
H14−0.13060.95540.26080.050*
C15−0.2488 (2)0.84365 (17)0.20738 (8)0.0511 (4)
H15−0.30790.77500.21660.061*
C16−0.3753 (2)0.9351 (2)0.19154 (10)0.0695 (6)
H16A−0.39220.98370.22580.083*
H16B−0.48090.90280.18040.083*
C17−0.2033 (3)0.8788 (2)0.10353 (9)0.0636 (5)
H17A−0.28940.83360.08560.076*
H17B−0.11750.89100.07360.076*
C18−0.1970 (2)0.84189 (14)0.32279 (8)0.0447 (4)
C19−0.2712 (3)0.74099 (17)0.33593 (10)0.0611 (5)
H19−0.28150.68810.30580.073*
C20−0.3297 (3)0.71840 (19)0.39317 (11)0.0664 (6)
H20−0.38050.65120.40140.080*
C21−0.3120 (3)0.79610 (19)0.43776 (9)0.0585 (5)
C22−0.2352 (3)0.89380 (18)0.42702 (9)0.0594 (5)
H22−0.22100.94500.45790.071*
C23−0.1785 (2)0.91603 (15)0.36953 (9)0.0507 (4)
H23−0.12620.98310.36210.061*
C240.1702 (2)0.89594 (14)0.27369 (8)0.0441 (4)
C250.3441 (3)0.8996 (3)0.35799 (12)0.0927 (9)
H25A0.44690.89970.33630.139*
H25B0.35840.86190.39570.139*
H25C0.30990.97430.36540.139*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0877 (4)0.1109 (5)0.0676 (3)0.0124 (4)0.0262 (3)0.0256 (3)
S10.0624 (3)0.0981 (4)0.0715 (3)0.0219 (3)−0.0083 (3)0.0120 (3)
O10.0696 (9)0.0436 (7)0.1053 (12)0.0169 (7)0.0198 (9)0.0080 (7)
O20.0752 (10)0.0577 (8)0.0764 (9)−0.0241 (8)−0.0210 (8)0.0036 (7)
O30.0568 (8)0.0881 (10)0.0630 (9)−0.0065 (8)−0.0181 (7)0.0179 (8)
N10.0377 (7)0.0616 (9)0.0536 (8)−0.0053 (7)−0.0014 (6)−0.0136 (7)
C10.0361 (7)0.0378 (8)0.0490 (9)−0.0001 (6)−0.0001 (7)−0.0084 (6)
C20.0380 (8)0.0436 (8)0.0622 (10)−0.0047 (7)0.0031 (8)−0.0183 (8)
C30.0396 (9)0.0584 (10)0.0560 (10)−0.0130 (8)0.0042 (7)−0.0246 (8)
C40.0552 (11)0.0717 (12)0.0488 (10)−0.0096 (10)0.0044 (8)−0.0121 (9)
C50.0699 (13)0.1004 (16)0.0549 (11)−0.0197 (13)0.0044 (10)−0.0034 (12)
C60.0671 (15)0.140 (3)0.0586 (14)−0.0266 (18)0.0179 (12)−0.0136 (15)
C70.0525 (12)0.117 (2)0.0743 (15)−0.0184 (14)0.0228 (11)−0.0421 (16)
C80.0415 (9)0.0743 (13)0.0783 (14)−0.0148 (10)0.0118 (9)−0.0323 (11)
C90.0540 (12)0.0672 (14)0.125 (2)−0.0026 (11)0.0293 (14)−0.0387 (15)
C100.0567 (12)0.0478 (11)0.136 (2)0.0087 (10)0.0226 (15)−0.0153 (13)
C110.0502 (10)0.0388 (9)0.0899 (15)−0.0004 (8)0.0112 (10)−0.0130 (9)
C120.0566 (11)0.0405 (9)0.0739 (13)0.0020 (8)0.0084 (10)0.0057 (8)
C130.0345 (7)0.0346 (7)0.0510 (9)0.0001 (6)0.0008 (7)−0.0017 (6)
C140.0337 (7)0.0401 (8)0.0511 (9)−0.0012 (6)0.0019 (7)−0.0004 (7)
C150.0374 (8)0.0641 (10)0.0518 (10)−0.0081 (7)0.0012 (7)−0.0060 (8)
C160.0389 (10)0.1115 (17)0.0580 (11)0.0141 (11)−0.0023 (8)−0.0057 (12)
C170.0440 (9)0.0976 (16)0.0491 (10)−0.0024 (11)−0.0040 (9)−0.0129 (10)
C180.0350 (8)0.0460 (8)0.0530 (9)−0.0001 (7)0.0004 (7)0.0019 (7)
C190.0650 (12)0.0503 (10)0.0680 (12)−0.0094 (9)0.0068 (10)−0.0009 (9)
C200.0659 (13)0.0591 (11)0.0742 (13)−0.0068 (10)0.0101 (11)0.0146 (10)
C210.0465 (10)0.0742 (12)0.0547 (10)0.0105 (10)0.0059 (8)0.0164 (9)
C220.0547 (11)0.0701 (12)0.0535 (10)0.0023 (10)−0.0019 (9)−0.0027 (9)
C230.0442 (9)0.0528 (9)0.0553 (10)−0.0042 (7)−0.0006 (8)−0.0006 (8)
C240.0336 (8)0.0499 (9)0.0489 (9)0.0028 (7)0.0009 (7)−0.0022 (7)
C250.0586 (14)0.150 (3)0.0690 (15)−0.0026 (16)−0.0224 (12)−0.0050 (16)

Geometric parameters (Å, °)

Cl1—C211.7473 (19)C10—C111.413 (3)
S1—C161.803 (2)C10—H100.9300
S1—C171.831 (2)C12—C131.519 (2)
O1—C111.363 (3)C12—H12A0.9700
O1—C121.433 (3)C12—H12B0.9700
O2—C241.188 (2)C13—C241.520 (2)
O3—C241.316 (2)C13—C141.553 (2)
O3—C251.450 (3)C14—C181.511 (2)
N1—C171.435 (3)C14—C151.533 (2)
N1—C151.484 (2)C14—H140.9800
N1—C11.485 (2)C15—C161.547 (3)
C1—C21.507 (2)C15—H150.9800
C1—C131.519 (2)C16—H16A0.9700
C1—H10.9800C16—H16B0.9700
C2—C111.366 (3)C17—H17A0.9700
C2—C31.429 (3)C17—H17B0.9700
C3—C41.404 (3)C18—C231.380 (3)
C3—C81.429 (3)C18—C191.392 (3)
C4—C51.370 (3)C19—C201.382 (3)
C4—H40.9300C19—H190.9300
C5—C61.406 (4)C20—C211.373 (3)
C5—H50.9300C20—H200.9300
C6—C71.348 (4)C21—C221.357 (3)
C6—H60.9300C22—C231.381 (3)
C7—C81.410 (4)C22—H220.9300
C7—H70.9300C23—H230.9300
C8—C91.390 (4)C25—H25A0.9600
C9—C101.358 (4)C25—H25B0.9600
C9—H90.9300C25—H25C0.9600
C16—S1—C1786.54 (11)C24—C13—C14109.79 (13)
C11—O1—C12117.08 (16)C18—C14—C15116.91 (14)
C24—O3—C25115.36 (19)C18—C14—C13117.39 (14)
C17—N1—C15108.65 (15)C15—C14—C13103.06 (14)
C17—N1—C1115.64 (16)C18—C14—H14106.2
C15—N1—C1107.59 (13)C15—C14—H14106.2
N1—C1—C2113.81 (13)C13—C14—H14106.2
N1—C1—C13102.20 (14)N1—C15—C14105.76 (13)
C2—C1—C13111.28 (14)N1—C15—C16109.84 (16)
N1—C1—H1109.8C14—C15—C16112.78 (16)
C2—C1—H1109.8N1—C15—H15109.5
C13—C1—H1109.8C14—C15—H15109.5
C11—C2—C3118.79 (17)C16—C15—H15109.5
C11—C2—C1119.09 (17)C15—C16—S1106.49 (13)
C3—C2—C1122.02 (16)C15—C16—H16A110.4
C4—C3—C2123.46 (17)S1—C16—H16A110.4
C4—C3—C8117.4 (2)C15—C16—H16B110.4
C2—C3—C8119.1 (2)S1—C16—H16B110.4
C5—C4—C3122.0 (2)H16A—C16—H16B108.6
C5—C4—H4119.0N1—C17—S1106.90 (13)
C3—C4—H4119.0N1—C17—H17A110.3
C4—C5—C6119.7 (3)S1—C17—H17A110.3
C4—C5—H5120.1N1—C17—H17B110.3
C6—C5—H5120.1S1—C17—H17B110.3
C7—C6—C5120.1 (2)H17A—C17—H17B108.6
C7—C6—H6120.0C23—C18—C19117.43 (17)
C5—C6—H6120.0C23—C18—C14118.64 (15)
C6—C7—C8121.6 (2)C19—C18—C14123.92 (16)
C6—C7—H7119.2C20—C19—C18120.9 (2)
C8—C7—H7119.2C20—C19—H19119.6
C9—C8—C7121.7 (2)C18—C19—H19119.6
C9—C8—C3119.2 (2)C21—C20—C19119.39 (19)
C7—C8—C3119.0 (2)C21—C20—H20120.3
C10—C9—C8121.2 (2)C19—C20—H20120.3
C10—C9—H9119.4C22—C21—C20121.25 (18)
C8—C9—H9119.4C22—C21—Cl1119.01 (18)
C9—C10—C11119.9 (2)C20—C21—Cl1119.70 (17)
C9—C10—H10120.0C21—C22—C23118.9 (2)
C11—C10—H10120.0C21—C22—H22120.5
O1—C11—C2124.87 (17)C23—C22—H22120.5
O1—C11—C10113.6 (2)C18—C23—C22122.07 (18)
C2—C11—C10121.5 (2)C18—C23—H23119.0
O1—C12—C13111.22 (16)C22—C23—H23119.0
O1—C12—H12A109.4O2—C24—O3123.72 (17)
C13—C12—H12A109.4O2—C24—C13124.82 (16)
O1—C12—H12B109.4O3—C24—C13111.43 (15)
C13—C12—H12B109.4O3—C25—H25A109.5
H12A—C12—H12B108.0O3—C25—H25B109.5
C12—C13—C1109.08 (15)H25A—C25—H25B109.5
C12—C13—C24112.97 (15)O3—C25—H25C109.5
C1—C13—C24110.94 (14)H25A—C25—H25C109.5
C12—C13—C14112.92 (14)H25B—C25—H25C109.5
C1—C13—C14100.46 (13)
C17—N1—C1—C2−83.59 (19)C2—C1—C13—C14−166.96 (12)
C15—N1—C1—C2154.79 (16)C12—C13—C14—C1853.3 (2)
C17—N1—C1—C13156.33 (15)C1—C13—C14—C18169.33 (14)
C15—N1—C1—C1334.71 (17)C24—C13—C14—C18−73.75 (18)
N1—C1—C2—C11−94.1 (2)C12—C13—C14—C15−76.75 (19)
C13—C1—C2—C1120.8 (2)C1—C13—C14—C1539.28 (16)
N1—C1—C2—C389.84 (19)C24—C13—C14—C15156.20 (14)
C13—C1—C2—C3−155.34 (15)C17—N1—C15—C14−135.34 (16)
C11—C2—C3—C4−173.48 (17)C1—N1—C15—C14−9.46 (19)
C1—C2—C3—C42.6 (3)C17—N1—C15—C16−13.4 (2)
C11—C2—C3—C85.5 (2)C1—N1—C15—C16112.51 (17)
C1—C2—C3—C8−178.41 (15)C18—C14—C15—N1−149.27 (15)
C2—C3—C4—C5−178.47 (18)C13—C14—C15—N1−18.92 (18)
C8—C3—C4—C52.6 (3)C18—C14—C15—C1690.68 (19)
C3—C4—C5—C6−0.2 (3)C13—C14—C15—C16−138.98 (16)
C4—C5—C6—C7−2.0 (4)N1—C15—C16—S1−18.99 (19)
C5—C6—C7—C81.7 (4)C14—C15—C16—S198.69 (16)
C6—C7—C8—C9−176.9 (2)C17—S1—C16—C1534.61 (15)
C6—C7—C8—C30.7 (3)C15—N1—C17—S139.89 (18)
C4—C3—C8—C9174.88 (19)C1—N1—C17—S1−81.16 (16)
C2—C3—C8—C9−4.1 (3)C16—S1—C17—N1−44.10 (15)
C4—C3—C8—C7−2.8 (3)C15—C14—C18—C23−138.51 (17)
C2—C3—C8—C7178.22 (17)C13—C14—C18—C2398.24 (19)
C7—C8—C9—C10177.1 (2)C15—C14—C18—C1941.0 (2)
C3—C8—C9—C10−0.4 (3)C13—C14—C18—C19−82.2 (2)
C8—C9—C10—C113.6 (4)C23—C18—C19—C202.5 (3)
C12—O1—C11—C212.4 (3)C14—C18—C19—C20−176.99 (19)
C12—O1—C11—C10−170.33 (19)C18—C19—C20—C21−1.0 (3)
C3—C2—C11—O1174.65 (18)C19—C20—C21—C22−1.3 (3)
C1—C2—C11—O1−1.6 (3)C19—C20—C21—Cl1176.54 (18)
C3—C2—C11—C10−2.4 (3)C20—C21—C22—C231.9 (3)
C1—C2—C11—C10−178.61 (18)Cl1—C21—C22—C23−175.99 (16)
C9—C10—C11—O1−179.5 (2)C19—C18—C23—C22−2.0 (3)
C9—C10—C11—C2−2.2 (3)C14—C18—C23—C22177.58 (17)
C11—O1—C12—C13−41.6 (3)C21—C22—C23—C18−0.2 (3)
O1—C12—C13—C159.6 (2)C25—O3—C24—O2−0.4 (3)
O1—C12—C13—C24−64.3 (2)C25—O3—C24—C13−178.41 (17)
O1—C12—C13—C14170.33 (16)C12—C13—C24—O2149.37 (19)
N1—C1—C13—C1273.74 (17)C1—C13—C24—O226.5 (2)
C2—C1—C13—C12−48.09 (18)C14—C13—C24—O2−83.6 (2)
N1—C1—C13—C24−161.19 (13)C12—C13—C24—O3−32.6 (2)
C2—C1—C13—C2476.98 (16)C1—C13—C24—O3−155.50 (15)
N1—C1—C13—C14−45.13 (15)C14—C13—C24—O394.37 (17)

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the chlorophenyl ring.
D—H···AD—HH···AD···AD—H···A
C12—H12B···N10.972.572.903 (3)100
C25—H25A···Cgi0.962.793.431 (3)125

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5001).

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