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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2536.
Published online 2010 September 11. doi:  10.1107/S1600536810035592
PMCID: PMC2983318

Ethyl 6-amino-5-cyano-2,4-bis­(4-methyl­phen­yl)-4H-pyran-3-carboxyl­ate

Abstract

In the title compound, C23H22N2O3, the pyran ring adopts a twisted boat conformation. The tolyl rings and carboxyl­ate group are attached to the pyran ring with torsion angles of −77.1 (2), 59.5 (3) and 17.8 (3)°, respectively. The ethyl group is disordered over two orientations with a site-occupancy ratio of 0.508 (5):0.492 (5). In the crystal, mol­ecules are linked by N—H(...)N and N—H(...)O hydrogen bonds, generating a chain running the a axis. Weak C—H(...)O, C—H(...)N and C—H(...)π inter­actions are also observed.

Related literature

For the use of related compounds in organic synthesis, see: Liang et al. (2009 [triangle]). For the synthesis, see: Vasuki & Kumaravel (2008 [triangle]). For conformational analysis, see: Cremer & Pople (1975 [triangle]). For related structures, see: Athimoolam et al. (2007 [triangle]); Kannan et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2536-scheme1.jpg

Experimental

Crystal data

  • C23H22N2O3
  • M r = 374.43
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2536-efi2.jpg
  • a = 8.3485 (2) Å
  • b = 11.4057 (3) Å
  • c = 11.6689 (3) Å
  • α = 72.902 (2)°
  • β = 72.690 (2)°
  • γ = 89.182 (2)°
  • V = 1010.64 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.30 × 0.20 × 0.20 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2004 [triangle]) T min = 0.981, T max = 0.984
  • 18989 measured reflections
  • 3554 independent reflections
  • 2971 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.192
  • S = 1.04
  • 3554 reflections
  • 243 parameters
  • 7 restraints
  • H-atom parameters constrained
  • Δρmax = 0.56 e Å−3
  • Δρmin = −0.58 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: APEX2 and SAINT (Bruker, 2004 [triangle]); data reduction: SAINT and XPREP (Bruker, 2004 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035592/ng5024sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035592/ng5024Isup2.hkl

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

Acknowledgments

The authors acknowledge the Centre of Excellence in Bioinformatics, Pondicherry University, for providing facilities and GV thanks the Department of Science and Technology, New Delhi, Government of India, (No. SR/S5/ GC-22/2007) for financial support.

supplementary crystallographic information

Comment

Like the title compounds some of the related compounds are widely used as organic intermediates in organic chemistry (Liang et al., 2009). The title compound was synthesized by using Rapid four-component reactions in water (Vasuki & Kumaravel, 2008) and undertaken this study.

In the title compound (I), the pyran (A) ring adopts screw-boat conformation with the puckering parameters: Amplitude (Q) =0.221 (2) Å, Theta (θ) = 101.3 (5)° and Phi ([var phi]) = 17.6 (7)°(Cremer & Pople, 1975), the puckered C11 atom having the maximum deviation of 0.137 (3) Å. The one toluene ring (Fig. 1) deviates significantly from planarity and attached with pyran ring by an (+)-syn-clinal conformation with torsion angle (C6—C5—C8—C12) of 59.5 (3)°, whereas the other toluene ring does not deviates from planarity and attached with pyran ring by torsion angle (C10—C11—C17—C22) of -77.1 (2)°, indiacting an (-)-syn-clinal conformtion. The carboxylate group is attached to pyran ring at C12 with the torsion angle of C11—C12—C13—O3 = 17.8 (3)°, indicating an (+)-syn-periplanar conformation. Moreover the O-ethyl group of carboxylate is disordered with the refined site-occupancy ratio of 0.508 (5)/0.492 (5). The two N—H···N and one N—H···O intermolecular interactions with a distance of 3.081 (4) Å and 3.088 (3) Å respectively are observed (Fig 2), in which the N—H···N intermolecular interaction forms R22 (12) ring motifs. The weak C—H···O, C—H···N and C—H···π [Cg: centroid of C17, C18, C19, C20, C21 and C22] (Fig. 3) intermolecular interaction also stabilized their three dimensional network of the crystal packing with a distance of 3.432 (3) Å, 3.318 (3) Å and 3.770 (4) Å respectively.

Experimental

The title compound was prepared by the successive addition of 4-methylbenzaldehyde(0.240 g, 2 mmol) and piperidine (5 mol %) to a stirred aqueous mixture of malononitrile(0.132 g, 2 mmol) and ethyl 3-oxo-3-p-tolyl propanoate (0.412 g, 2 mmol) at room temperature under an open atmosphere with vigorous stirring for 5–10 min. The precipitated solid was filtered, washed with water and then with a mixture of ethylacetate/hexane (20:80) (Vasuki & Kumaravel, 2008). The product obtained was pure by TLC and 1H NMR spectroscopy. However, the products were further purified by recrystallization from ethanol. Analysis calculated for ethyl6-amino-5-cyano-2, 4-bis (4-methylphenyl)-4H-pyran-3-carboxylate showed that it has C23 H22 N2 O3.

Refinement

The non-hydrogen atoms where refined anisotropically whereas hydrogen atoms were refined isotropically. The C—H and amine H atoms were positioned geometrically (C—H= 0.93–0.97 and N—H=0.86 Å) and were refined, using riding model with Uiso(H) = xUeq(C), where x = 1.5 for methyl and 1.2 for all other atoms. The O-ethyl group of carboxylate shows disordered in two postition in the final refinement, the occupancy factors of two possible sites, O2B/C14B/C15B and O2A/C14A/C15A, converged to 0.508 (5) and 0.492 (5). For the disordered unit, the distance of C—C and C—O bond restrained to be 1.53 (10) Å and 1.43 (10) Å respectively.

Figures

Fig. 1.
: The molecular structure of (I), showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level. The O-ethyl group is disordered over two positions with site-occupancy factor, from refinement of 0.508 (5) and 0.492 (5). ...
Fig. 2.
: The crystal packing of (I), showing intermolecular hydrogen bonding interactions as dashed lines.
Fig. 3.
: A view of R22 (12) ring motifs formed by N—H···N interaction between to molecules and viewed along b* axis. The ring forming atoms are shown in ball and stick model and the Hydrogen bond are shown in green dashed lines. ...
Fig. 4.
: The molecular interaction showing the weak C—H···pi interaction between two molecules (dashed line in blue color), In which the Cg is the centriod of C17—C22 ring. The disordered B section of the molecules omited ...

Crystal data

C23H22N2O3Z = 2
Mr = 374.43F(000) = 396
Triclinic, P1Dx = 1.230 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.3485 (2) ÅCell parameters from 9717 reflections
b = 11.4057 (3) Åθ = 2.2–32°
c = 11.6689 (3) ŵ = 0.08 mm1
α = 72.902 (2)°T = 293 K
β = 72.690 (2)°Rectangular, colourless
γ = 89.182 (2)°0.30 × 0.20 × 0.20 mm
V = 1010.64 (4) Å3

Data collection

Bruker Kappa APEXII CCD diffractometer3554 independent reflections
Radiation source: fine-focus sealed tube2971 reflections with I > 2σ(I)
graphiteRint = 0.022
Detector resolution: 0 pixels mm-1θmax = 25.0°, θmin = 1.9°
ω and [var phi] scanh = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2004)k = −13→13
Tmin = 0.981, Tmax = 0.984l = −13→13
18989 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.192w = 1/[σ2(Fo2) + (0.0869P)2 + 0.7661P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.025
3554 reflectionsΔρmax = 0.56 e Å3
243 parametersΔρmin = −0.58 e Å3
7 restraintsExtinction correction: SHELXL
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0

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*/UeqOcc. (<1)
C10.4425 (5)0.8123 (3)0.3388 (4)0.0986 (13)
H1A0.34520.79590.41200.148*
H1B0.42060.87390.27010.148*
H1C0.53690.84120.35680.148*
C20.4816 (3)0.69499 (14)0.30303 (19)0.0648 (8)
C30.4067 (2)0.58140 (17)0.38598 (15)0.0720 (9)
H30.32820.57690.46310.086*
C40.4491 (2)0.47452 (13)0.35366 (15)0.0618 (7)
H40.39900.39850.40920.074*
C50.5664 (2)0.48123 (12)0.23840 (15)0.0473 (6)
C60.6414 (2)0.59482 (15)0.15545 (14)0.0718 (9)
H60.71990.59930.07830.086*
C70.5990 (3)0.70170 (12)0.18776 (18)0.0803 (10)
H70.64910.77770.13230.096*
C80.6149 (3)0.3670 (2)0.2054 (2)0.0449 (5)
C90.4918 (3)0.2162 (2)0.1459 (2)0.0466 (6)
C100.6432 (3)0.1734 (2)0.1069 (2)0.0472 (6)
C110.7915 (3)0.2049 (2)0.1436 (2)0.0453 (6)
H110.89140.22070.06950.054*
C120.7648 (3)0.3221 (2)0.1804 (2)0.0453 (6)
C130.9216 (3)0.3763 (2)0.1813 (2)0.0532 (6)
O2A0.8984 (11)0.4720 (4)0.2391 (6)0.0562 (13)0.492 (5)
C14A1.0588 (11)0.5280 (9)0.2238 (9)0.072 (2)0.492 (5)
H14A1.12080.56570.13570.086*0.492 (5)
H14B1.12620.46920.26340.086*0.492 (5)
C15A1.0050 (13)0.6246 (9)0.2921 (12)0.122 (3)0.492 (5)
H15A0.93310.67820.25390.184*0.492 (5)
H15B1.10290.67190.28620.184*0.492 (5)
H15C0.94530.58440.37910.184*0.492 (5)
O2B0.8938 (10)0.4347 (5)0.2773 (4)0.0562 (13)0.508 (5)
C14B1.0311 (12)0.5012 (7)0.2866 (8)0.072 (2)0.508 (5)
H14C1.12600.45070.28280.086*0.508 (5)
H14D0.99840.51590.36790.086*0.508 (5)
C15B1.0869 (14)0.6244 (7)0.1830 (9)0.122 (3)0.508 (5)
H15D1.10800.61180.10220.184*0.508 (5)
H15E1.18790.65920.18770.184*0.508 (5)
H15F0.99970.67960.19410.184*0.508 (5)
C160.6647 (3)0.0898 (2)0.0364 (3)0.0536 (6)
C170.82337 (19)0.09928 (12)0.24806 (13)0.0442 (5)
C180.95357 (19)0.02588 (15)0.21696 (12)0.0555 (6)
H181.02040.04200.13370.067*
C190.9840 (2)−0.07159 (15)0.31037 (16)0.0649 (7)
H191.0711−0.12070.28960.078*
C200.8841 (2)−0.09565 (14)0.43487 (14)0.0596 (7)
C210.7539 (2)−0.02225 (16)0.46597 (11)0.0626 (7)
H210.6871−0.03830.54930.075*
C220.72354 (18)0.07522 (15)0.37256 (15)0.0568 (7)
H220.63640.12430.39340.068*
C230.9202 (5)−0.1997 (3)0.5378 (3)0.0826 (10)
H23A0.9932−0.16820.57360.124*
H23B0.9736−0.26180.50260.124*
H23C0.8165−0.23490.60230.124*
N10.6900 (3)0.0234 (3)−0.0223 (3)0.0743 (8)
N20.3450 (3)0.1811 (2)0.1388 (2)0.0598 (6)
H2A0.33890.12380.10580.072*
H2B0.25600.21570.16720.072*
O10.4731 (2)0.30688 (16)0.20301 (18)0.0545 (5)
O31.0577 (2)0.35407 (19)0.1320 (2)0.0723 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.112 (3)0.087 (2)0.135 (3)0.041 (2)−0.050 (3)−0.079 (3)
C20.0700 (18)0.0665 (18)0.086 (2)0.0278 (14)−0.0392 (16)−0.0500 (16)
C30.0619 (17)0.088 (2)0.081 (2)0.0153 (15)−0.0124 (15)−0.0570 (19)
C40.0554 (16)0.0655 (17)0.0693 (17)0.0027 (13)−0.0092 (13)−0.0376 (14)
C50.0441 (12)0.0527 (14)0.0593 (14)0.0138 (10)−0.0217 (11)−0.0324 (12)
C60.093 (2)0.0535 (16)0.0626 (17)0.0186 (15)−0.0089 (16)−0.0245 (14)
C70.110 (3)0.0493 (16)0.080 (2)0.0200 (16)−0.0216 (19)−0.0258 (15)
C80.0424 (12)0.0490 (13)0.0520 (13)0.0063 (10)−0.0163 (10)−0.0264 (11)
C90.0454 (13)0.0517 (13)0.0560 (14)0.0103 (10)−0.0202 (11)−0.0318 (11)
C100.0441 (13)0.0514 (13)0.0591 (14)0.0115 (10)−0.0191 (11)−0.0329 (12)
C110.0371 (12)0.0496 (13)0.0564 (14)0.0096 (10)−0.0132 (10)−0.0281 (11)
C120.0429 (13)0.0448 (12)0.0553 (14)0.0074 (10)−0.0161 (10)−0.0249 (11)
C130.0471 (14)0.0437 (13)0.0726 (17)0.0051 (10)−0.0212 (12)−0.0204 (12)
O2A0.0596 (13)0.029 (3)0.092 (3)0.007 (2)−0.037 (3)−0.022 (3)
C14A0.067 (3)0.061 (4)0.100 (6)−0.011 (3)−0.031 (5)−0.035 (5)
C15A0.127 (7)0.093 (4)0.177 (8)−0.009 (4)−0.073 (6)−0.058 (6)
O2B0.0596 (13)0.029 (3)0.092 (3)0.007 (2)−0.037 (3)−0.022 (3)
C14B0.067 (3)0.061 (4)0.100 (6)−0.011 (3)−0.031 (5)−0.035 (5)
C15B0.127 (7)0.093 (4)0.177 (8)−0.009 (4)−0.073 (6)−0.058 (6)
C160.0396 (13)0.0638 (15)0.0714 (17)0.0123 (11)−0.0192 (12)−0.0396 (14)
C170.0354 (11)0.0472 (12)0.0590 (14)0.0056 (9)−0.0157 (10)−0.0283 (11)
C180.0460 (14)0.0573 (15)0.0624 (16)0.0134 (11)−0.0101 (12)−0.0238 (13)
C190.0545 (16)0.0587 (16)0.079 (2)0.0183 (13)−0.0179 (14)−0.0213 (14)
C200.0549 (15)0.0535 (15)0.0720 (18)−0.0024 (12)−0.0233 (13)−0.0170 (13)
C210.0607 (17)0.0669 (17)0.0587 (16)0.0007 (13)−0.0117 (13)−0.0233 (14)
C220.0497 (14)0.0629 (16)0.0636 (16)0.0121 (12)−0.0136 (12)−0.0318 (13)
C230.083 (2)0.0685 (19)0.089 (2)−0.0005 (16)−0.0342 (19)−0.0051 (17)
N10.0520 (13)0.0912 (18)0.108 (2)0.0174 (12)−0.0227 (13)−0.0750 (17)
N20.0434 (11)0.0730 (15)0.0879 (16)0.0170 (10)−0.0276 (11)−0.0542 (13)
O10.0403 (9)0.0644 (11)0.0780 (12)0.0137 (8)−0.0196 (8)−0.0489 (10)
O30.0395 (10)0.0768 (13)0.1065 (16)0.0053 (9)−0.0157 (10)−0.0432 (12)

Geometric parameters (Å, °)

C1—C21.518 (3)C14A—C15A1.5295 (10)
C1—H1A0.9600C14A—H14A0.9700
C1—H1B0.9600C14A—H14B0.9700
C1—H1C0.9600C15A—H15A0.9600
C2—C31.3900C15A—H15B0.9600
C2—C71.3900C15A—H15C0.9600
C3—C41.3900O2B—C14B1.4309 (10)
C3—H30.9300C14B—C15B1.5295 (10)
C4—C51.3900C14B—H14C0.9700
C4—H40.9300C14B—H14D0.9700
C5—C61.3900C15B—H15D0.9600
C5—C81.482 (2)C15B—H15E0.9600
C6—C71.3900C15B—H15F0.9600
C6—H60.9300C16—N11.140 (3)
C7—H70.9300C17—C181.3900
C8—C121.329 (3)C17—C221.3900
C8—O11.388 (3)C18—C191.3900
C9—N21.328 (3)C18—H180.9300
C9—C101.347 (3)C19—C201.3900
C9—O11.371 (3)C19—H190.9300
C10—C161.410 (3)C20—C211.3900
C10—C111.505 (3)C20—C231.520 (3)
C11—C121.514 (3)C21—C221.3900
C11—C171.525 (3)C21—H210.9300
C11—H110.9800C22—H220.9300
C12—C131.460 (3)C23—H23A0.9600
C13—O31.172 (3)C23—H23B0.9600
C13—O2A1.4256 (10)C23—H23C0.9600
C13—O2B1.4261 (10)N2—H2A0.8600
O2A—C14A1.4309 (10)N2—H2B0.8600
C2—C1—H1A109.5O2A—C14A—C15A100.8 (5)
C2—C1—H1B109.5O2A—C14A—H14A111.6
H1A—C1—H1B109.5C15A—C14A—H14A111.6
C2—C1—H1C109.5O2A—C14A—H14B111.6
H1A—C1—H1C109.5C15A—C14A—H14B111.6
H1B—C1—H1C109.5H14A—C14A—H14B109.4
C3—C2—C7120.0C13—O2B—C14B119.8 (6)
C3—C2—C1120.8 (2)O2B—C14B—C15B113.5 (6)
C7—C2—C1119.1 (2)O2B—C14B—H14C108.9
C4—C3—C2120.0C15B—C14B—H14C108.8
C4—C3—H3120.0O2B—C14B—H14D108.9
C2—C3—H3120.0C15B—C14B—H14D108.9
C3—C4—C5120.0H14C—C14B—H14D107.7
C3—C4—H4120.0C14B—C15B—H15D109.5
C5—C4—H4120.0C14B—C15B—H15E109.5
C6—C5—C4120.0H15D—C15B—H15E109.5
C6—C5—C8120.01 (14)C14B—C15B—H15F109.5
C4—C5—C8119.97 (14)H15D—C15B—H15F109.5
C5—C6—C7120.0H15E—C15B—H15F109.5
C5—C6—H6120.0N1—C16—C10176.8 (3)
C7—C6—H6120.0C18—C17—C22120.0
C6—C7—C2120.0C18—C17—C11118.98 (12)
C6—C7—H7120.0C22—C17—C11121.02 (12)
C2—C7—H7120.0C17—C18—C19120.0
C12—C8—O1121.7 (2)C17—C18—H18120.0
C12—C8—C5129.4 (2)C19—C18—H18120.0
O1—C8—C5108.85 (17)C20—C19—C18120.0
N2—C9—C10128.6 (2)C20—C19—H19120.0
N2—C9—O1110.53 (19)C18—C19—H19120.0
C10—C9—O1120.9 (2)C19—C20—C21120.0
C9—C10—C16120.4 (2)C19—C20—C23120.16 (18)
C9—C10—C11122.1 (2)C21—C20—C23119.81 (18)
C16—C10—C11117.4 (2)C20—C21—C22120.0
C10—C11—C12109.30 (18)C20—C21—H21120.0
C10—C11—C17111.98 (19)C22—C21—H21120.0
C12—C11—C17111.80 (18)C21—C22—C17120.0
C10—C11—H11107.9C21—C22—H22120.0
C12—C11—H11107.9C17—C22—H22120.0
C17—C11—H11107.9C20—C23—H23A109.5
C8—C12—C13126.6 (2)C20—C23—H23B109.5
C8—C12—C11121.9 (2)H23A—C23—H23B109.5
C13—C12—C11111.49 (18)C20—C23—H23C109.5
O3—C13—O2A120.1 (4)H23A—C23—H23C109.5
O3—C13—O2B120.3 (4)H23B—C23—H23C109.5
O2A—C13—O2B20.6 (4)C9—N2—H2A120.0
O3—C13—C12125.93 (19)C9—N2—H2B120.0
O2A—C13—C12113.7 (4)H2A—N2—H2B120.0
O2B—C13—C12111.8 (4)C9—O1—C8119.48 (17)
C13—O2A—C14A109.7 (5)
C7—C2—C3—C40.0C8—C12—C13—O2A13.2 (5)
C1—C2—C3—C4−177.4 (2)C11—C12—C13—O2A−168.1 (3)
C2—C3—C4—C50.0C8—C12—C13—O2B35.5 (4)
C3—C4—C5—C60.0C11—C12—C13—O2B−145.8 (3)
C3—C4—C5—C8178.43 (18)O3—C13—O2A—C14A0.6 (7)
C4—C5—C6—C70.0O2B—C13—O2A—C14A97.0 (19)
C8—C5—C6—C7−178.43 (18)C12—C13—O2A—C14A−174.0 (5)
C5—C6—C7—C20.0C13—O2A—C14A—C15A−179.6 (8)
C3—C2—C7—C60.0O3—C13—O2B—C14B20.1 (7)
C1—C2—C7—C6177.5 (2)O2A—C13—O2B—C14B−75.7 (19)
C6—C5—C8—C1259.5 (3)C12—C13—O2B—C14B−175.3 (5)
C4—C5—C8—C12−118.9 (3)C13—O2B—C14B—C15B73.4 (11)
C6—C5—C8—O1−120.33 (18)C9—C10—C16—N1163 (6)
C4—C5—C8—O161.2 (2)C11—C10—C16—N1−21 (6)
N2—C9—C10—C167.7 (5)C10—C11—C17—C18102.33 (18)
O1—C9—C10—C16−173.2 (2)C12—C11—C17—C18−134.63 (16)
N2—C9—C10—C11−167.9 (3)C10—C11—C17—C22−77.07 (19)
O1—C9—C10—C1111.2 (4)C12—C11—C17—C2246.0 (2)
C9—C10—C11—C12−22.1 (3)C22—C17—C18—C190.0
C16—C10—C11—C12162.2 (2)C11—C17—C18—C19−179.41 (16)
C9—C10—C11—C17102.4 (3)C17—C18—C19—C200.0
C16—C10—C11—C17−73.3 (3)C18—C19—C20—C210.0
O1—C8—C12—C13−179.3 (2)C18—C19—C20—C23−178.2 (2)
C5—C8—C12—C130.8 (4)C19—C20—C21—C220.0
O1—C8—C12—C112.1 (4)C23—C20—C21—C22178.2 (2)
C5—C8—C12—C11−177.8 (2)C20—C21—C22—C170.0
C10—C11—C12—C815.4 (3)C18—C17—C22—C210.0
C17—C11—C12—C8−109.1 (3)C11—C17—C22—C21179.39 (16)
C10—C11—C12—C13−163.4 (2)N2—C9—O1—C8−171.9 (2)
C17—C11—C12—C1372.1 (2)C10—C9—O1—C88.8 (4)
C8—C12—C13—O3−160.9 (3)C12—C8—O1—C9−15.7 (4)
C11—C12—C13—O317.8 (4)C5—C8—O1—C9164.2 (2)

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C17–C22 ring.
D—H···AD—HH···AD···AD—H···A
N2—H2A···N1i0.862.223.081 (3)177
N2—H2B···O3ii0.862.313.088 (3)150
C6—H6···O3iii0.932.513.432 (2)171
C18—H18···N1iv0.932.603.318 (3)135
C23—H23A···Cgv0.922.853.770 (4)160

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5024).

References

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