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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2376–o2377.
Published online 2010 August 21. doi:  10.1107/S1600536810033295
PMCID: PMC3007989

5-[(E)-2-Bromo­benzyl­idene]-8-(2-bromo­phen­yl)-2-hy­droxy-10-methyl-3,10-di­aza­hexa­cyclo­[10.7.1.13,7.02,11.07,11.016,20]henicosa-1(20),12,14,16,18-pentaen-6-one

Abstract

In the title compound, C33H26Br2N2O2, the piperidine group adopts an envelope conformation while the two pyrrolidine groups adopt half-chair and envelope conformations. The dihydro­acenaphthyl­ene group is almost planar, with a maximum deviation of 0.105 (1) Å. The dihedral angle between the two bromo­phenyl rings is 60.19 (8)°. An intra­molecular O—H(...)N inter­action is observed, generating an S(5) ring motif. The crystal structure is stabilized by inter­molecular C—H(...)O inter­actions. Short Br(...)Br [3.461 (1) Å] and Br(...)C [3.322 (2) Å] inter­molecular contacts are observed, as well as π–π inter­actions [centroid–centroid distance = 3.793 (1) Å].

Related literature

For biological studies of five-membered heterocycles, pyrrolidines and piperidines, see: Shi et al. (2009 [triangle]); Nair & Suja (2007 [triangle]); Nájera & Sansano (2005 [triangle]); Coldham & Hufton (2005 [triangle]); Daly et al. (1986 [triangle]); El-Subbagh et al. (2000 [triangle]); Dimmock et al. (2001 [triangle]). For ring puckering analysis, see: Cremer & Pople (1975 [triangle]). For the graph-set description of hydrogen-bond ring motifs, see: Bernstein et al. (1995 [triangle]). For a closely related crystal structure, see: Kumar et al. (2010 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2376-scheme1.jpg

Experimental

Crystal data

  • C33H26Br2N2O2
  • M r = 642.38
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2376-efi1.jpg
  • a = 8.3334 (14) Å
  • b = 12.4213 (19) Å
  • c = 12.8062 (19) Å
  • α = 80.623 (4)°
  • β = 79.787 (4)°
  • γ = 88.213 (4)°
  • V = 1287.2 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 3.19 mm−1
  • T = 100 K
  • 0.52 × 0.41 × 0.19 mm

Data collection

  • Bruker APEXII DUO CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.288, T max = 0.584
  • 27238 measured reflections
  • 9152 independent reflections
  • 8233 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.026
  • wR(F 2) = 0.105
  • S = 1.18
  • 9152 reflections
  • 357 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.99 e Å−3
  • Δρmin = −1.17 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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/S1600536810033295/wn2405sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033295/wn2405Isup2.hkl

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

Acknowledgments

The synthetic chemistry work was funded by Universiti Sains Malaysia (USM) under University Research Grant No. 1001/PKIMIA/811016 and RSK thanks Universiti Sains Malaysia for the award of a post-doctoral fellowship. HKF thanks Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

supplementary crystallographic information

Comment

Multi-component 1,3-dipolar cycloaddition of ylidic species, such as azomethine ylides with olefinic dipolarophiles, plays a key role in the construction of biologically active five-membered heterocycles (Shi et al., 2009; Nair et al., 2007; Nájera et al., 2005; Coldham et al., 2005). Highly substituted pyrrolidines have gained much importance since they form the central skeleton of many natural products (Daly et al., 1986). Heterocycles with the piperidine substructure display important biological activities, such as cytotoxic and anticancer activities (El-Subbagh et al., 2000 ; Dimmock et al., 2001). Because of the biological importance of these heterocycles, the crystal structure determination of the title compound was carried out and the results are presented in this paper.

All geometrical parameters of the title compound (Fig.1) are within normal ranges and comparable with those in a previously reported structure (Kumar et al., 2010). The piperidine (N1/C8-C12) ring adopts an envelope confirmation [Q = 0.617 (2) Å, Θ = 44.6 (2)°, [var phi]= 60.6 (2)°; Cremer & Pople, 1975]. The two five-membered pyrrolidine rings, (N1/C10-C11/C13-C14) and (N2/C10/C13/C25-C26), adopt half-chair and envelope comformations respectively [Q = 0.452 (2) Å, [var phi]= 198.8 (2)° and Q = 0.401 (2) Å, [var phi]= 352.9 (2)°]. The dihydroacenaphthylene group, (C13-C24) is almost planar, with a maximum deviation of 0.105 (1) Å for atom C13. The dihedral angle between the two bromophenyl rings (C1-C6) and (C27-C32) is 60.19 (8)°.

An intramolecular O2—H1O2···N2 hydrogen bond (Table 1) forms a five-membered ring, generating an S(5) hydrogen bond ring motif (Bernstein et al., 1995). In the crystal structure, molecules are connected by intermolecular C—H···O hydrogen bonds (Table 1, Fig. 2). Short intermolecular contacts Br2···Br2 [3.461 (1)Å] and Br1···C29 [3.322 (2)Å] are also observed. The crystal structure is further stabilized by π-π interactions with Cg1···Cg1 = 3.793 (1) Å, where Cg1 is the centroid of the C1-C6 benzene ring.

Experimental

A mixture of 3,5-bis[(E)-(2-bromophenyl)methylidene]tetrahydro-4(1H)-pyridinone (0.100 g, 0.231 mmol), acenaphthenequinone (0.042 g, 0.231 mmol) and sarcosine (0.021 g, 0.231 mmol) was dissolved in methanol (10 ml) and refluxed for 1 hour. After completion of the reaction, as evident from TLC, the mixture was poured into water (50 ml). The precipitated solid was filtered, washed with water and recrystallised from a petroleum ether-ethyl acetate mixture (1:1) to yield the title compound as pale yellow crystals.

Refinement

The H atom attached to O2 was located in a difference map and refined isotropically [O—H = 0.75 (3) Å]. The remaining H atoms were positioned geometrically and refined using a riding model [C—H = 0.93 Å for Csp2, 0.96 Å for methyl C, 0.97 Å for methylene C and 0.98 Å for methine C]; Uiso(H) = xUeq(C), where x = 1.5 for methyl H and 1.2 for all other H atoms. A rotating model was used for the methyl group.

Figures

Fig. 1.
The molecular structure, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms are shown as spheres of arbitrary radius.
Fig. 2.
The crystal packing of the title compound, viewed down the a axis. Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.

Crystal data

C33H26Br2N2O2Z = 2
Mr = 642.38F(000) = 648
Triclinic, P1Dx = 1.657 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.3334 (14) ÅCell parameters from 9995 reflections
b = 12.4213 (19) Åθ = 3.3–35.1°
c = 12.8062 (19) ŵ = 3.19 mm1
α = 80.623 (4)°T = 100 K
β = 79.787 (4)°Block, yellow
γ = 88.213 (4)°0.52 × 0.41 × 0.19 mm
V = 1287.2 (3) Å3

Data collection

Bruker APEXII DUO CCD area-detector diffractometer9152 independent reflections
Radiation source: fine-focus sealed tube8233 reflections with I > 2σ(I)
graphiteRint = 0.022
[var phi] and ω scansθmax = 32.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −12→12
Tmin = 0.288, Tmax = 0.584k = −18→18
27238 measured reflectionsl = −19→19

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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.18w = 1/[σ2(Fo2) + (0.0672P)2 + 0.2037P] where P = (Fo2 + 2Fc2)/3
9152 reflections(Δ/σ)max = 0.004
357 parametersΔρmax = 0.99 e Å3
0 restraintsΔρmin = −1.17 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br10.856585 (19)1.068250 (12)0.386199 (13)0.01626 (5)
Br21.025391 (18)0.886819 (12)−0.064263 (12)0.01437 (5)
O10.65922 (15)0.94414 (9)0.09019 (9)0.0152 (2)
O20.55092 (14)0.49704 (9)0.16200 (10)0.0131 (2)
N10.70944 (16)0.61925 (10)0.22074 (10)0.0111 (2)
N20.45256 (16)0.66041 (10)0.02417 (10)0.0109 (2)
C10.5433 (2)0.80453 (13)0.49862 (13)0.0169 (3)
H1A0.48520.75680.47050.020*
C20.5306 (2)0.79520 (14)0.60979 (14)0.0193 (3)
H2A0.46660.74060.65510.023*
C30.6137 (2)0.86754 (14)0.65250 (13)0.0193 (3)
H3A0.60540.86140.72660.023*
C40.7092 (2)0.94912 (13)0.58513 (13)0.0173 (3)
H4A0.76360.99850.61380.021*
C50.72276 (19)0.95632 (12)0.47468 (12)0.0131 (2)
C60.64227 (19)0.88461 (12)0.42811 (12)0.0132 (2)
C70.65161 (19)0.89702 (12)0.31078 (12)0.0139 (3)
H7A0.63840.96720.27490.017*
C80.67730 (18)0.81722 (12)0.25027 (12)0.0124 (2)
C90.67026 (18)0.84990 (12)0.13230 (12)0.0117 (2)
C100.66598 (17)0.75367 (11)0.07288 (11)0.0104 (2)
C110.78932 (18)0.66652 (12)0.11188 (12)0.0122 (2)
H11A0.80860.61130.06550.015*
H11B0.89240.69980.11340.015*
C120.71804 (19)0.69952 (12)0.29215 (12)0.0135 (2)
H12A0.82750.69780.30840.016*
H12B0.64430.67640.35920.016*
C130.49859 (17)0.69498 (11)0.11969 (11)0.0101 (2)
C140.54394 (17)0.59505 (11)0.20430 (11)0.0106 (2)
C150.41293 (18)0.59321 (12)0.30260 (12)0.0115 (2)
C160.3780 (2)0.52059 (13)0.39629 (13)0.0161 (3)
H16A0.43950.45730.40760.019*
C170.2453 (2)0.54430 (14)0.47598 (13)0.0189 (3)
H17A0.22090.49530.53970.023*
C180.1516 (2)0.63738 (14)0.46208 (13)0.0182 (3)
H18A0.06640.65060.51610.022*
C190.18568 (19)0.71303 (12)0.36501 (12)0.0137 (2)
C200.10036 (19)0.81138 (13)0.33826 (13)0.0153 (3)
H20A0.01300.83210.38690.018*
C210.14739 (19)0.87631 (12)0.23970 (13)0.0148 (3)
H21A0.09020.94060.22370.018*
C220.27944 (18)0.84897 (12)0.16176 (12)0.0128 (2)
H22A0.30840.89450.09620.015*
C230.36326 (17)0.75363 (11)0.18568 (11)0.0106 (2)
C240.31619 (18)0.68768 (12)0.28712 (12)0.0113 (2)
C250.50120 (18)0.75089 (12)−0.06406 (12)0.0128 (2)
H25A0.42500.8112−0.05890.015*
H25B0.50530.7274−0.13310.015*
C260.67185 (18)0.78475 (12)−0.05064 (11)0.0112 (2)
H26A0.68100.8643−0.06990.013*
C270.81308 (18)0.73321 (12)−0.11802 (11)0.0117 (2)
C280.97428 (18)0.76858 (12)−0.12970 (12)0.0120 (2)
C291.10552 (19)0.72043 (13)−0.18784 (12)0.0149 (3)
H29A1.21060.7463−0.19300.018*
C301.0790 (2)0.63323 (13)−0.23832 (13)0.0173 (3)
H30A1.16610.5992−0.27620.021*
C310.9204 (2)0.59773 (13)−0.23128 (13)0.0170 (3)
H31A0.90110.5409−0.26660.020*
C320.7901 (2)0.64644 (13)−0.17176 (12)0.0150 (3)
H32A0.68510.6208−0.16750.018*
C330.28025 (18)0.63124 (12)0.03566 (12)0.0132 (2)
H33A0.26410.6003−0.02570.020*
H33B0.21390.69540.04050.020*
H33C0.25010.57890.09970.020*
H1O20.547 (4)0.516 (2)0.104 (2)0.028 (7)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.01810 (8)0.01305 (8)0.01711 (8)−0.00218 (5)−0.00054 (6)−0.00328 (6)
Br20.01454 (8)0.01177 (8)0.01788 (8)−0.00154 (5)−0.00447 (5)−0.00345 (5)
O10.0200 (5)0.0107 (4)0.0152 (5)−0.0001 (4)−0.0042 (4)−0.0015 (4)
O20.0173 (5)0.0089 (4)0.0143 (5)0.0019 (4)−0.0043 (4)−0.0039 (4)
N10.0120 (5)0.0103 (5)0.0112 (5)0.0008 (4)−0.0027 (4)−0.0017 (4)
N20.0113 (5)0.0117 (5)0.0100 (5)−0.0005 (4)−0.0021 (4)−0.0017 (4)
C10.0182 (7)0.0154 (6)0.0167 (7)−0.0008 (5)−0.0006 (5)−0.0035 (5)
C20.0225 (7)0.0163 (7)0.0164 (7)−0.0009 (6)0.0025 (6)−0.0006 (5)
C30.0255 (8)0.0194 (7)0.0124 (6)0.0030 (6)−0.0032 (6)−0.0016 (5)
C40.0206 (7)0.0176 (7)0.0148 (6)0.0013 (5)−0.0045 (5)−0.0048 (5)
C50.0141 (6)0.0113 (6)0.0137 (6)0.0014 (5)−0.0021 (5)−0.0024 (5)
C60.0149 (6)0.0122 (6)0.0126 (6)0.0016 (5)−0.0020 (5)−0.0031 (5)
C70.0155 (6)0.0122 (6)0.0143 (6)0.0001 (5)−0.0031 (5)−0.0027 (5)
C80.0138 (6)0.0114 (6)0.0125 (6)−0.0003 (5)−0.0035 (5)−0.0021 (5)
C90.0107 (6)0.0115 (6)0.0135 (6)−0.0013 (4)−0.0026 (5)−0.0031 (5)
C100.0110 (5)0.0094 (5)0.0107 (6)0.0002 (4)−0.0019 (4)−0.0016 (4)
C110.0111 (6)0.0120 (6)0.0131 (6)0.0015 (5)−0.0028 (5)−0.0008 (5)
C120.0167 (6)0.0115 (6)0.0135 (6)−0.0003 (5)−0.0058 (5)−0.0026 (5)
C130.0112 (5)0.0083 (5)0.0105 (5)0.0008 (4)−0.0014 (4)−0.0011 (4)
C140.0118 (6)0.0081 (5)0.0124 (6)0.0010 (4)−0.0029 (4)−0.0024 (4)
C150.0122 (6)0.0103 (5)0.0118 (6)0.0002 (4)−0.0018 (5)−0.0011 (4)
C160.0190 (7)0.0131 (6)0.0151 (6)0.0017 (5)−0.0027 (5)0.0004 (5)
C170.0198 (7)0.0188 (7)0.0146 (7)0.0006 (6)0.0007 (5)0.0031 (5)
C180.0180 (7)0.0197 (7)0.0142 (6)0.0014 (6)0.0019 (5)−0.0002 (5)
C190.0133 (6)0.0135 (6)0.0141 (6)0.0007 (5)−0.0009 (5)−0.0031 (5)
C200.0139 (6)0.0151 (6)0.0175 (7)0.0030 (5)−0.0019 (5)−0.0059 (5)
C210.0145 (6)0.0130 (6)0.0178 (7)0.0042 (5)−0.0039 (5)−0.0045 (5)
C220.0142 (6)0.0108 (6)0.0137 (6)0.0017 (5)−0.0037 (5)−0.0015 (5)
C230.0109 (5)0.0095 (5)0.0116 (6)0.0008 (4)−0.0022 (4)−0.0024 (4)
C240.0115 (6)0.0105 (5)0.0121 (6)0.0005 (4)−0.0025 (5)−0.0017 (5)
C250.0126 (6)0.0140 (6)0.0112 (6)−0.0001 (5)−0.0024 (5)−0.0002 (5)
C260.0119 (6)0.0109 (5)0.0104 (6)0.0003 (4)−0.0017 (4)−0.0012 (4)
C270.0132 (6)0.0110 (6)0.0104 (6)−0.0011 (5)−0.0011 (5)−0.0010 (4)
C280.0136 (6)0.0104 (6)0.0117 (6)0.0001 (5)−0.0022 (5)−0.0013 (5)
C290.0132 (6)0.0157 (6)0.0147 (6)0.0007 (5)−0.0006 (5)−0.0014 (5)
C300.0191 (7)0.0164 (7)0.0158 (7)0.0023 (5)0.0000 (5)−0.0041 (5)
C310.0211 (7)0.0141 (6)0.0159 (6)−0.0006 (5)−0.0009 (5)−0.0053 (5)
C320.0160 (6)0.0143 (6)0.0147 (6)−0.0029 (5)−0.0004 (5)−0.0046 (5)
C330.0113 (6)0.0137 (6)0.0149 (6)−0.0007 (5)−0.0022 (5)−0.0037 (5)

Geometric parameters (Å, °)

Br1—C51.8963 (15)C14—C151.511 (2)
Br2—C281.8993 (15)C15—C161.370 (2)
O1—C91.2144 (18)C15—C241.410 (2)
O2—C141.4065 (17)C16—C171.424 (2)
O2—H1O20.75 (3)C16—H16A0.9300
N1—C111.4697 (19)C17—C181.380 (2)
N1—C121.4698 (19)C17—H17A0.9300
N1—C141.4785 (19)C18—C191.421 (2)
N2—C331.4680 (19)C18—H18A0.9300
N2—C251.4684 (19)C19—C241.405 (2)
N2—C131.4750 (19)C19—C201.418 (2)
C1—C21.395 (2)C20—C211.382 (2)
C1—C61.407 (2)C20—H20A0.9300
C1—H1A0.9300C21—C221.421 (2)
C2—C31.385 (3)C21—H21A0.9300
C2—H2A0.9300C22—C231.3749 (19)
C3—C41.388 (2)C22—H22A0.9300
C3—H3A0.9300C23—C241.416 (2)
C4—C51.387 (2)C25—C261.542 (2)
C4—H4A0.9300C25—H25A0.9700
C5—C61.397 (2)C25—H25B0.9700
C6—C71.474 (2)C26—C271.521 (2)
C7—C81.344 (2)C26—H26A0.9800
C7—H7A0.9300C27—C281.402 (2)
C8—C91.510 (2)C27—C321.405 (2)
C8—C121.523 (2)C28—C291.387 (2)
C9—C101.522 (2)C29—C301.391 (2)
C10—C111.554 (2)C29—H29A0.9300
C10—C261.558 (2)C30—C311.389 (2)
C10—C131.569 (2)C30—H30A0.9300
C11—H11A0.9700C31—C321.394 (2)
C11—H11B0.9700C31—H31A0.9300
C12—H12A0.9700C32—H32A0.9300
C12—H12B0.9700C33—H33A0.9600
C13—C231.526 (2)C33—H33B0.9600
C13—C141.592 (2)C33—H33C0.9600
C14—O2—H1O2103 (2)C16—C15—C14132.30 (13)
C11—N1—C12108.02 (12)C24—C15—C14108.17 (12)
C11—N1—C14102.44 (11)C15—C16—C17118.42 (14)
C12—N1—C14115.63 (11)C15—C16—H16A120.8
C33—N2—C25112.31 (12)C17—C16—H16A120.8
C33—N2—C13114.95 (12)C18—C17—C16122.38 (15)
C25—N2—C13105.24 (11)C18—C17—H17A118.8
C2—C1—C6121.38 (16)C16—C17—H17A118.8
C2—C1—H1A119.3C17—C18—C19119.82 (14)
C6—C1—H1A119.3C17—C18—H18A120.1
C3—C2—C1119.73 (16)C19—C18—H18A120.1
C3—C2—H2A120.1C24—C19—C20116.51 (14)
C1—C2—H2A120.1C24—C19—C18116.89 (14)
C2—C3—C4120.28 (15)C20—C19—C18126.60 (14)
C2—C3—H3A119.9C21—C20—C19119.84 (14)
C4—C3—H3A119.9C21—C20—H20A120.1
C5—C4—C3119.32 (15)C19—C20—H20A120.1
C5—C4—H4A120.3C20—C21—C22122.79 (14)
C3—C4—H4A120.3C20—C21—H21A118.6
C4—C5—C6122.33 (14)C22—C21—H21A118.6
C4—C5—Br1117.66 (12)C23—C22—C21118.38 (14)
C6—C5—Br1120.00 (11)C23—C22—H22A120.8
C5—C6—C1116.92 (14)C21—C22—H22A120.8
C5—C6—C7121.47 (14)C22—C23—C24118.82 (13)
C1—C6—C7121.48 (14)C22—C23—C13132.51 (13)
C8—C7—C6126.64 (14)C24—C23—C13108.52 (12)
C8—C7—H7A116.7C19—C24—C15122.94 (13)
C6—C7—H7A116.7C19—C24—C23123.65 (13)
C7—C8—C9116.44 (13)C15—C24—C23113.41 (13)
C7—C8—C12124.44 (14)N2—C25—C26105.15 (11)
C9—C8—C12119.08 (12)N2—C25—H25A110.7
O1—C9—C8122.98 (13)C26—C25—H25A110.7
O1—C9—C10123.03 (13)N2—C25—H25B110.7
C8—C9—C10113.85 (12)C26—C25—H25B110.7
C9—C10—C11108.11 (12)H25A—C25—H25B108.8
C9—C10—C26114.98 (11)C27—C26—C25114.83 (12)
C11—C10—C26117.57 (11)C27—C26—C10113.94 (12)
C9—C10—C13106.44 (11)C25—C26—C10102.43 (11)
C11—C10—C13101.86 (11)C27—C26—H26A108.4
C26—C10—C13106.49 (11)C25—C26—H26A108.4
N1—C11—C10104.01 (11)C10—C26—H26A108.4
N1—C11—H11A111.0C28—C27—C32115.83 (13)
C10—C11—H11A111.0C28—C27—C26122.18 (13)
N1—C11—H11B111.0C32—C27—C26121.98 (13)
C10—C11—H11B111.0C29—C28—C27123.13 (14)
H11A—C11—H11B109.0C29—C28—Br2115.84 (11)
N1—C12—C8116.67 (12)C27—C28—Br2121.03 (11)
N1—C12—H12A108.1C28—C29—C30119.60 (15)
C8—C12—H12A108.1C28—C29—H29A120.2
N1—C12—H12B108.1C30—C29—H29A120.2
C8—C12—H12B108.1C31—C30—C29119.04 (15)
H12A—C12—H12B107.3C31—C30—H30A120.5
N2—C13—C23114.26 (12)C29—C30—H30A120.5
N2—C13—C10102.66 (11)C30—C31—C32120.60 (15)
C23—C13—C10119.66 (11)C30—C31—H31A119.7
N2—C13—C14112.84 (11)C32—C31—H31A119.7
C23—C13—C14103.45 (11)C31—C32—C27121.75 (15)
C10—C13—C14103.78 (11)C31—C32—H32A119.1
O2—C14—N1108.22 (11)C27—C32—H32A119.1
O2—C14—C15112.29 (12)N2—C33—H33A109.5
N1—C14—C15114.63 (12)N2—C33—H33B109.5
O2—C14—C13110.91 (11)H33A—C33—H33B109.5
N1—C14—C13105.17 (11)N2—C33—H33C109.5
C15—C14—C13105.37 (11)H33A—C33—H33C109.5
C16—C15—C24119.53 (14)H33B—C33—H33C109.5
C6—C1—C2—C31.5 (3)C10—C13—C14—C15135.81 (11)
C1—C2—C3—C40.0 (3)O2—C14—C15—C1651.9 (2)
C2—C3—C4—C5−1.0 (3)N1—C14—C15—C16−72.2 (2)
C3—C4—C5—C60.5 (2)C13—C14—C15—C16172.71 (16)
C3—C4—C5—Br1−179.35 (13)O2—C14—C15—C24−128.68 (13)
C4—C5—C6—C11.0 (2)N1—C14—C15—C24107.29 (14)
Br1—C5—C6—C1−179.16 (11)C13—C14—C15—C24−7.84 (15)
C4—C5—C6—C7176.88 (15)C24—C15—C16—C17−0.9 (2)
Br1—C5—C6—C7−3.2 (2)C14—C15—C16—C17178.52 (16)
C2—C1—C6—C5−2.0 (2)C15—C16—C17—C18−0.1 (3)
C2—C1—C6—C7−177.90 (15)C16—C17—C18—C190.5 (3)
C5—C6—C7—C8135.05 (17)C17—C18—C19—C240.0 (2)
C1—C6—C7—C8−49.2 (2)C17—C18—C19—C20179.44 (16)
C6—C7—C8—C9175.99 (14)C24—C19—C20—C210.0 (2)
C6—C7—C8—C12−6.2 (3)C18—C19—C20—C21−179.40 (16)
C7—C8—C9—O17.5 (2)C19—C20—C21—C220.2 (2)
C12—C8—C9—O1−170.38 (14)C20—C21—C22—C230.2 (2)
C7—C8—C9—C10−168.33 (13)C21—C22—C23—C24−0.9 (2)
C12—C8—C9—C1013.77 (19)C21—C22—C23—C13174.12 (15)
O1—C9—C10—C11142.12 (15)N2—C13—C23—C22−61.5 (2)
C8—C9—C10—C11−42.03 (16)C10—C13—C23—C2260.7 (2)
O1—C9—C10—C268.5 (2)C14—C13—C23—C22175.42 (15)
C8—C9—C10—C26−175.62 (12)N2—C13—C23—C24113.85 (13)
O1—C9—C10—C13−109.10 (16)C10—C13—C23—C24−123.91 (13)
C8—C9—C10—C1366.74 (15)C14—C13—C23—C24−9.21 (15)
C12—N1—C11—C10−73.52 (14)C20—C19—C24—C15179.51 (14)
C14—N1—C11—C1049.00 (13)C18—C19—C24—C15−1.0 (2)
C9—C10—C11—N173.21 (14)C20—C19—C24—C23−0.8 (2)
C26—C10—C11—N1−154.57 (12)C18—C19—C24—C23178.75 (15)
C13—C10—C11—N1−38.68 (13)C16—C15—C24—C191.5 (2)
C11—N1—C12—C844.67 (17)C14—C15—C24—C19−178.07 (14)
C14—N1—C12—C8−69.37 (17)C16—C15—C24—C23−178.31 (14)
C7—C8—C12—N1168.00 (15)C14—C15—C24—C232.16 (17)
C9—C8—C12—N1−14.3 (2)C22—C23—C24—C191.2 (2)
C33—N2—C13—C23−31.95 (17)C13—C23—C24—C19−174.92 (14)
C25—N2—C13—C2392.16 (14)C22—C23—C24—C15−179.05 (14)
C33—N2—C13—C10−163.06 (11)C13—C23—C24—C154.84 (17)
C25—N2—C13—C10−38.96 (13)C33—N2—C25—C26169.39 (11)
C33—N2—C13—C1485.87 (14)C13—N2—C25—C2643.64 (14)
C25—N2—C13—C14−150.02 (12)N2—C25—C26—C2795.36 (14)
C9—C10—C13—N2143.27 (11)N2—C25—C26—C10−28.69 (13)
C11—C10—C13—N2−103.58 (12)C9—C10—C26—C27122.63 (13)
C26—C10—C13—N220.15 (13)C11—C10—C26—C27−6.42 (18)
C9—C10—C13—C2315.49 (17)C13—C10—C26—C27−119.76 (13)
C11—C10—C13—C23128.64 (13)C9—C10—C26—C25−112.74 (13)
C26—C10—C13—C23−107.63 (14)C11—C10—C26—C25118.21 (13)
C9—C10—C13—C14−99.04 (12)C13—C10—C26—C254.87 (13)
C11—C10—C13—C1414.11 (13)C25—C26—C27—C28168.94 (13)
C26—C10—C13—C14137.84 (11)C10—C26—C27—C28−73.35 (17)
C11—N1—C14—O279.77 (13)C25—C26—C27—C32−11.6 (2)
C12—N1—C14—O2−163.02 (12)C10—C26—C27—C32106.11 (16)
C11—N1—C14—C15−154.06 (12)C32—C27—C28—C29−1.7 (2)
C12—N1—C14—C15−36.85 (17)C26—C27—C28—C29177.82 (14)
C11—N1—C14—C13−38.81 (13)C32—C27—C28—Br2178.85 (11)
C12—N1—C14—C1378.40 (14)C26—C27—C28—Br2−1.7 (2)
N2—C13—C14—O27.93 (16)C27—C28—C29—C300.5 (2)
C23—C13—C14—O2131.93 (12)Br2—C28—C29—C30179.96 (12)
C10—C13—C14—O2−102.44 (13)C28—C29—C30—C311.4 (2)
N2—C13—C14—N1124.69 (12)C29—C30—C31—C32−2.0 (3)
C23—C13—C14—N1−111.31 (12)C30—C31—C32—C270.7 (3)
C10—C13—C14—N114.32 (13)C28—C27—C32—C311.1 (2)
N2—C13—C14—C15−113.81 (13)C26—C27—C32—C31−178.41 (15)
C23—C13—C14—C1510.19 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H1O2···N20.75 (3)2.12 (3)2.6735 (18)132 (3)
C32—H32A···O2i0.932.473.374 (2)163
C33—H33A···O2i0.962.553.292 (2)134

Symmetry codes: (i) −x+1, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2405).

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