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ISSN: 2056-9890

2,2′,2′′-[(2,4,6-Trimeth­­oxy­benzene-1,3,5-tri­yl)tris­­(methyl­ene)]tris­­(iso­indole-1,3-dione)

aInstitut für Organische Chemie, Technische Universität Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
*Correspondence e-mail: monika.mazik@chemie.tu-freiberg.de

(Received 21 March 2013; accepted 27 March 2013; online 10 April 2013)

The title mol­ecule, C36H27N3O9, adopts an almost symmetric conformation in which the mean planes of the phthalimido units are inclined at dihedral angles of 81.1 (1), 85.3 (1) and 86.3 (1)° with respect to the plane of the central aromatic ring. The O atoms are involved in intra- and inter­molecular C—H⋯O hydrogen bonding. The crystal structure also features ππ arene inter­actions [minimum ring centroid separation = 3.683 (2) Å]. The present mode of non-covalent interactions leads to a three-dimensional supramolecular architecture.

Related literature

For hydrogen bonds in the solid state, see: Desiraju (2002[Desiraju, G. R. (2002). Acc. Chem. Res. 35, 565-573.]); Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond In Structural Chemistry and Biology. IUCR Monographs on Crystallography, Vol. 9. New York: Oxford University Press.]); Steiner (2002[Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.]). For C—H⋯O hydrogen bonds in ketones carrying a terminal pyridine subunit, see: Mazik et al. (2001[Mazik, M., Bläser, D. & Boese, R. (2001). Tetrahedron, 57, 5791-5797.]). For a review on acyclic receptors based on a benzene-derived core, see: Mazik (2009[Mazik, M. (2009). Chem. Soc. Rev. 38, 935-956.]).

[Scheme 1]

Experimental

Crystal data
  • C36H27N3O9

  • Mr = 645.61

  • Triclinic, [P \overline 1]

  • a = 10.2370 (3) Å

  • b = 10.3671 (3) Å

  • c = 14.6501 (4) Å

  • α = 79.804 (1)°

  • β = 79.512 (1)°

  • γ = 83.874 (1)°

  • V = 1500.20 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 100 K

  • 0.51 × 0.50 × 0.28 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.949, Tmax = 0.971

  • 29692 measured reflections

  • 8026 independent reflections

  • 6992 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.100

  • S = 0.96

  • 8026 reflections

  • 436 parameters

  • H-atom parameters constrained

  • Δρmax = 0.46 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C7—H7A⋯O8i 0.98 2.47 3.2068 (15) 132
C8—H8B⋯O5i 0.98 2.34 3.2920 (15) 165
C9—H9A⋯O4ii 0.98 2.56 3.4742 (15) 156
C9—H9C⋯O9 0.98 2.38 3.2684 (19) 151
C10—H10A⋯O4 0.99 2.54 2.9144 (14) 102
C10—H10B⋯O3 0.99 2.32 2.8017 (15) 109
C19—H19A⋯O7 0.99 2.54 2.9200 (15) 103
C19—H19B⋯O2 0.99 2.36 2.8457 (14) 109
C23—H23⋯O1iii 0.95 2.45 3.3231 (16) 153
C28—H28A⋯O8 0.99 2.52 2.9187 (16) 103
C28—H28B⋯O3 0.99 2.34 2.8289 (16) 109
C32—H32⋯O2iv 0.95 2.56 3.2917 (16) 134
C34—H34⋯O7v 0.95 2.46 3.4066 (15) 172
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y+1, -z; (iii) -x+1, -y+1, -z; (iv) -x+1, -y, -z+1; (v) x, y-1, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

Our interest in the title compound, C36H27N3O9, arises from its use as an important precursor in the synthesis of artificial receptors based on trimethoxybenzene-derived core (for a review on acyclic carbohydrate receptors containing a trimethyl- or triethylbenzene scaffold, see: Mazik, 2009). The title compound crystallizes in the space group P-1 with one molecule in the asymmetric part of the unit cell. The interplanar angles between the phthalimido residues are 6.67 (4) (B/C), 48.86 (3) (B/D) and 53.23 (3)° (C/D). According to the three-dimensional arrangement of substituents around the benzene ring the present conformational isomer can be named 1-up, 3,5-down tris(phthalimidomethyl), 2,4-up, 6-down- trimethoxybenzene. The molecular conformation is stabilized by seven C—H···O hydrogen bonds (Desiraju, 2002; Desiraju & Steiner, 1999; Mazik et al., 2001; Steiner, 2002) with phthalimido O atoms O(4), O(7), O(8), O(9) and the ether O atoms O(2), O(3) acting as acceptors [C—H···Ophthal 2.38 - 2.54 Å, C—H···Oether 2.32 - 2.36 Å). This high degree of intramolecular hydrogen bonding may explain the slight twist of the benzene ring with maximum atomic distances from the best plane being -0.044 (1) and 0.027 (1) Å for C(4) and C(3). The packing structure is stabilized by intermolecular C—H···O bonding [C—H···O 2.34 - 2.54 Å, 132.1 - 172.1 °] as well as face-to-face arene interactions (centroid···centroid distances 3.683 (2), 3.693 (2) Å].

Related literature top

For hydrogen bonds in the solid state, see: Desiraju (2002); Desiraju & Steiner (1999); Steiner (2002). For C—H···O hydrogen bonds in ketones carrying a terminal pyridine subunit, see: Mazik et al. (2001). For a review on acyclic receptors based on benzene-derived core, see: Mazik (2009).

Experimental top

A mixture of 1,3,5-tris(bromomethyl)-2,4,6-trimethoxybenzene (5.4 g, 12.0 mmol) and potassium phthalimide (10.0 g, 54.0 mmol) suspended in dry dimethyl sulfoxide (150 ml) was stirred at 120 °C for 8 h. After the mixture was cooled to room temperature, water (300 ml) was added and the formed precipitate was filtered and washed with water (400 ml). Then the precipitate was suspended in water (150 ml), and the suspension was extracted with chloroform (3 x 100 ml). The combined organic layers were washed with brine (100 ml) and water (100 ml), dried over magnesium sulfate and concentrated in vacuo. The desired product was obtained as a white solid after flash chromatography (SiO2, toluene/ethyl acetate 2:1 v/v, Rf = 0.37) in 46% yield (3.5 g, 5.5 mmol).

Analysis data: m.p. = 235 °C; 1H-NMR (400 MHz, CDCl3) δ 7.68 (m, 6H), 7.60 (m, 6H), 4.87 (s, 6H), 3.89 (s, 9H) p.p.m.; 13C-NMR (100 MHz, CDCl3) δ 167.83, 159.07, 133.55, 132.03, 122.95, 119.12, 62.21, 32.80 p.p.m..

Suitable crystals of the title compound for X-ray analysis were obtained by slow evaporation of a CHCl3 solution.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Perspective view of the title compound including the atom numbering. Anisotropic displacement parameters for non-hydrogen atoms are drawn at a 50% probability level.
[Figure 2] Fig. 2. Packing diagram of the title compound. Hydrogen bonds are displayed as broken lines, while broken double lines represent π···π arene interactions.
2,2',2''-[(2,4,6-Trimethoxybenzene-1,3,5-triyl)tris(methylene)]tris(isoindole-1,3-dione) top
Crystal data top
C36H27N3O9Z = 2
Mr = 645.61F(000) = 672
Triclinic, P1Dx = 1.429 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.2370 (3) ÅCell parameters from 9907 reflections
b = 10.3671 (3) Åθ = 2.3–29.2°
c = 14.6501 (4) ŵ = 0.10 mm1
α = 79.804 (1)°T = 100 K
β = 79.512 (1)°Irregular, colourless
γ = 83.874 (1)°0.51 × 0.50 × 0.28 mm
V = 1500.20 (7) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer
8026 independent reflections
Radiation source: fine-focus sealed tube6992 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
phi and ω scansθmax = 29.1°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1413
Tmin = 0.949, Tmax = 0.971k = 1414
29692 measured reflectionsl = 2020
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.0441P)2 + 0.958P]
where P = (Fo2 + 2Fc2)/3
8026 reflections(Δ/σ)max < 0.001
436 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C36H27N3O9γ = 83.874 (1)°
Mr = 645.61V = 1500.20 (7) Å3
Triclinic, P1Z = 2
a = 10.2370 (3) ÅMo Kα radiation
b = 10.3671 (3) ŵ = 0.10 mm1
c = 14.6501 (4) ÅT = 100 K
α = 79.804 (1)°0.51 × 0.50 × 0.28 mm
β = 79.512 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
8026 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
6992 reflections with I > 2σ(I)
Tmin = 0.949, Tmax = 0.971Rint = 0.021
29692 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 0.96Δρmax = 0.46 e Å3
8026 reflectionsΔρmin = 0.35 e Å3
436 parameters
Special details top

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
O10.12796 (8)0.66212 (7)0.18783 (5)0.01633 (15)
O20.22988 (8)0.36078 (8)0.45741 (5)0.01958 (17)
O30.12369 (9)0.28557 (9)0.30721 (6)0.02355 (18)
O40.00470 (9)0.69783 (9)0.00364 (6)0.02422 (18)
O50.30723 (8)0.65590 (9)0.27100 (6)0.02150 (17)
O60.48284 (9)0.35909 (9)0.24204 (6)0.02684 (19)
O70.38511 (8)0.80269 (8)0.17348 (6)0.02226 (17)
O80.15450 (10)0.11530 (9)0.61971 (6)0.0286 (2)
O90.16627 (11)0.05026 (11)0.31774 (7)0.0358 (2)
N10.13167 (9)0.64776 (9)0.14771 (6)0.01741 (18)
N20.40392 (9)0.57826 (9)0.22568 (7)0.01757 (18)
N30.13324 (10)0.10612 (10)0.46635 (7)0.0210 (2)
C10.00047 (10)0.47455 (10)0.24429 (7)0.01530 (19)
C20.10435 (10)0.54768 (10)0.25067 (7)0.01478 (19)
C30.18863 (10)0.50669 (11)0.31740 (7)0.0156 (2)
C40.15679 (11)0.39756 (11)0.38509 (7)0.0164 (2)
C50.05402 (11)0.32162 (11)0.38223 (8)0.0177 (2)
C60.02044 (11)0.35899 (11)0.30973 (8)0.0172 (2)
C70.08112 (12)0.77913 (11)0.22889 (8)0.0208 (2)
H7A0.01310.77450.25710.031*
H7B0.09130.85680.17990.031*
H7C0.13340.78540.27750.031*
C80.18680 (13)0.43689 (14)0.53196 (8)0.0265 (3)
H8A0.20090.52960.50790.040*
H8B0.23820.40530.58290.040*
H8C0.09190.42770.55600.040*
C90.09626 (15)0.20079 (13)0.23660 (9)0.0295 (3)
H9A0.06090.25160.17570.044*
H9B0.17870.16410.23190.044*
H9C0.03050.12910.25420.044*
C100.08810 (11)0.50962 (11)0.16956 (8)0.0177 (2)
H10A0.03950.48040.11100.021*
H10B0.16810.45920.19030.021*
C110.08304 (11)0.72973 (11)0.06444 (8)0.0187 (2)
C120.16249 (11)0.85805 (11)0.06850 (8)0.0191 (2)
C130.15858 (13)0.97272 (12)0.00389 (9)0.0247 (2)
H130.09770.97940.05370.030*
C140.24767 (14)1.07832 (13)0.02669 (9)0.0275 (3)
H140.24751.15860.01620.033*
C150.33658 (13)1.06813 (12)0.11105 (10)0.0270 (3)
H150.39451.14230.12550.032*
C160.34221 (12)0.95084 (12)0.17486 (9)0.0225 (2)
H160.40420.94280.23190.027*
C170.25397 (11)0.84723 (11)0.15155 (8)0.0181 (2)
C180.23948 (11)0.70940 (11)0.20107 (7)0.0172 (2)
C190.31307 (11)0.57446 (12)0.31515 (8)0.0191 (2)
H19A0.28720.66550.32710.023*
H19B0.36010.52800.36630.023*
C200.48423 (11)0.46919 (12)0.19829 (8)0.0194 (2)
C210.56744 (11)0.51949 (12)0.10683 (8)0.0187 (2)
C220.66502 (12)0.45525 (13)0.04912 (9)0.0234 (2)
H220.68920.36400.06480.028*
C230.72661 (12)0.52973 (14)0.03315 (9)0.0268 (3)
H230.79410.48830.07430.032*
C240.69162 (12)0.66280 (14)0.05616 (8)0.0263 (3)
H240.73410.71050.11340.032*
C250.59480 (12)0.72803 (13)0.00356 (8)0.0218 (2)
H250.57160.81960.01110.026*
C260.53433 (11)0.65336 (11)0.08482 (8)0.0179 (2)
C270.43267 (11)0.69367 (11)0.16284 (8)0.0176 (2)
C280.02137 (12)0.20410 (12)0.45709 (9)0.0229 (2)
H28A0.00950.23470.51830.028*
H28B0.05290.16220.44210.028*
C290.19020 (12)0.07027 (11)0.54809 (8)0.0200 (2)
C300.29838 (11)0.03345 (11)0.52684 (8)0.0189 (2)
C310.38234 (12)0.10727 (11)0.58341 (8)0.0210 (2)
H310.37720.09640.64710.025*
C320.47546 (13)0.19880 (13)0.54295 (10)0.0269 (3)
H320.53460.25160.57990.032*
C330.48304 (13)0.21396 (12)0.44909 (10)0.0279 (3)
H330.54820.27550.42290.033*
C340.39607 (13)0.13983 (12)0.39372 (9)0.0258 (3)
H340.40000.15030.33010.031*
C350.30401 (12)0.05075 (11)0.43437 (8)0.0204 (2)
C360.19708 (13)0.03783 (12)0.39463 (8)0.0230 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0186 (4)0.0158 (4)0.0135 (3)0.0023 (3)0.0002 (3)0.0014 (3)
O20.0177 (4)0.0257 (4)0.0146 (3)0.0032 (3)0.0047 (3)0.0021 (3)
O30.0212 (4)0.0260 (4)0.0239 (4)0.0106 (3)0.0042 (3)0.0005 (3)
O40.0219 (4)0.0305 (5)0.0179 (4)0.0017 (3)0.0002 (3)0.0014 (3)
O50.0215 (4)0.0266 (4)0.0153 (4)0.0039 (3)0.0015 (3)0.0006 (3)
O60.0302 (5)0.0228 (4)0.0264 (4)0.0015 (4)0.0057 (4)0.0001 (3)
O70.0208 (4)0.0216 (4)0.0243 (4)0.0010 (3)0.0020 (3)0.0056 (3)
O80.0334 (5)0.0295 (5)0.0180 (4)0.0082 (4)0.0013 (3)0.0033 (3)
O90.0465 (6)0.0388 (6)0.0265 (5)0.0001 (5)0.0157 (4)0.0095 (4)
N10.0163 (4)0.0197 (4)0.0152 (4)0.0014 (3)0.0030 (3)0.0003 (3)
N20.0150 (4)0.0211 (5)0.0163 (4)0.0027 (3)0.0009 (3)0.0031 (3)
N30.0231 (5)0.0189 (5)0.0190 (4)0.0004 (4)0.0030 (4)0.0004 (4)
C10.0141 (5)0.0177 (5)0.0134 (4)0.0003 (4)0.0016 (4)0.0020 (4)
C20.0145 (5)0.0166 (5)0.0119 (4)0.0005 (4)0.0007 (3)0.0021 (4)
C30.0139 (5)0.0193 (5)0.0136 (4)0.0013 (4)0.0007 (4)0.0039 (4)
C40.0144 (5)0.0203 (5)0.0133 (4)0.0024 (4)0.0018 (4)0.0022 (4)
C50.0163 (5)0.0181 (5)0.0162 (5)0.0002 (4)0.0004 (4)0.0005 (4)
C60.0149 (5)0.0191 (5)0.0169 (5)0.0031 (4)0.0010 (4)0.0017 (4)
C70.0221 (5)0.0191 (5)0.0209 (5)0.0011 (4)0.0021 (4)0.0052 (4)
C80.0266 (6)0.0377 (7)0.0148 (5)0.0056 (5)0.0050 (4)0.0064 (5)
C90.0396 (7)0.0272 (6)0.0254 (6)0.0136 (5)0.0121 (5)0.0009 (5)
C100.0174 (5)0.0190 (5)0.0171 (5)0.0017 (4)0.0054 (4)0.0012 (4)
C110.0176 (5)0.0227 (5)0.0157 (5)0.0041 (4)0.0044 (4)0.0001 (4)
C120.0182 (5)0.0217 (5)0.0179 (5)0.0037 (4)0.0053 (4)0.0006 (4)
C130.0252 (6)0.0257 (6)0.0217 (5)0.0053 (5)0.0051 (4)0.0031 (4)
C140.0316 (7)0.0212 (6)0.0290 (6)0.0029 (5)0.0104 (5)0.0043 (5)
C150.0269 (6)0.0213 (6)0.0340 (7)0.0006 (5)0.0102 (5)0.0040 (5)
C160.0214 (5)0.0237 (6)0.0237 (5)0.0023 (4)0.0051 (4)0.0051 (4)
C170.0177 (5)0.0200 (5)0.0177 (5)0.0036 (4)0.0062 (4)0.0010 (4)
C180.0164 (5)0.0210 (5)0.0153 (5)0.0024 (4)0.0053 (4)0.0026 (4)
C190.0168 (5)0.0267 (6)0.0144 (5)0.0050 (4)0.0012 (4)0.0043 (4)
C200.0164 (5)0.0237 (5)0.0197 (5)0.0021 (4)0.0054 (4)0.0052 (4)
C210.0152 (5)0.0245 (5)0.0184 (5)0.0032 (4)0.0042 (4)0.0063 (4)
C220.0188 (5)0.0291 (6)0.0258 (6)0.0003 (4)0.0052 (4)0.0127 (5)
C230.0177 (5)0.0432 (7)0.0231 (6)0.0041 (5)0.0005 (4)0.0169 (5)
C240.0207 (6)0.0422 (7)0.0175 (5)0.0104 (5)0.0003 (4)0.0076 (5)
C250.0188 (5)0.0289 (6)0.0190 (5)0.0069 (4)0.0041 (4)0.0030 (4)
C260.0139 (5)0.0244 (5)0.0170 (5)0.0034 (4)0.0030 (4)0.0059 (4)
C270.0138 (5)0.0229 (5)0.0171 (5)0.0037 (4)0.0036 (4)0.0038 (4)
C280.0193 (5)0.0224 (6)0.0227 (5)0.0006 (4)0.0019 (4)0.0057 (4)
C290.0208 (5)0.0184 (5)0.0178 (5)0.0009 (4)0.0001 (4)0.0010 (4)
C300.0187 (5)0.0173 (5)0.0193 (5)0.0026 (4)0.0007 (4)0.0026 (4)
C310.0203 (5)0.0207 (5)0.0203 (5)0.0008 (4)0.0004 (4)0.0022 (4)
C320.0201 (6)0.0252 (6)0.0322 (6)0.0021 (5)0.0015 (5)0.0016 (5)
C330.0246 (6)0.0212 (6)0.0364 (7)0.0008 (5)0.0021 (5)0.0085 (5)
C340.0291 (6)0.0236 (6)0.0254 (6)0.0064 (5)0.0026 (5)0.0104 (5)
C350.0220 (5)0.0186 (5)0.0209 (5)0.0051 (4)0.0012 (4)0.0041 (4)
C360.0270 (6)0.0210 (5)0.0219 (5)0.0054 (4)0.0042 (4)0.0034 (4)
Geometric parameters (Å, º) top
O1—C21.3810 (13)C11—C121.4881 (16)
O1—C71.4465 (13)C12—C131.3816 (16)
O2—C41.3829 (13)C12—C171.3889 (16)
O2—C81.4372 (14)C13—C141.3955 (19)
O3—C61.3761 (13)C13—H130.9500
O3—C91.4439 (16)C14—C151.3899 (19)
O4—C111.2080 (14)C14—H140.9500
O5—C181.2085 (14)C15—C161.3960 (18)
O6—C201.2063 (15)C15—H150.9500
O7—C271.2067 (14)C16—C171.3772 (16)
O8—C291.2042 (14)C16—H160.9500
O9—C361.2060 (15)C17—C181.4889 (16)
N1—C181.3964 (14)C19—H19A0.9900
N1—C111.4000 (14)C19—H19B0.9900
N1—C101.4511 (14)C20—C211.4915 (16)
N2—C271.3972 (14)C21—C221.3806 (16)
N2—C201.3991 (15)C21—C261.3878 (16)
N2—C191.4596 (14)C22—C231.3944 (18)
N3—C361.3953 (15)C22—H220.9500
N3—C291.4009 (15)C23—C241.385 (2)
N3—C281.4564 (15)C23—H230.9500
C1—C21.3956 (15)C24—C251.3985 (17)
C1—C61.4048 (15)C24—H240.9500
C1—C101.5176 (15)C25—C261.3811 (16)
C2—C31.4008 (15)C25—H250.9500
C3—C41.3905 (15)C26—C271.4858 (15)
C3—C191.5116 (15)C28—H28A0.9900
C4—C51.3902 (16)C28—H28B0.9900
C5—C61.3947 (15)C29—C301.4894 (16)
C5—C281.5098 (15)C30—C311.3804 (16)
C7—H7A0.9800C30—C351.3877 (16)
C7—H7B0.9800C31—C321.4004 (17)
C7—H7C0.9800C31—H310.9500
C8—H8A0.9800C32—C331.3987 (19)
C8—H8B0.9800C32—H320.9500
C8—H8C0.9800C33—C341.392 (2)
C9—H9A0.9800C33—H330.9500
C9—H9B0.9800C34—C351.3786 (16)
C9—H9C0.9800C34—H340.9500
C10—H10A0.9900C35—C361.4862 (17)
C10—H10B0.9900
C2—O1—C7112.85 (8)C17—C16—C15117.15 (11)
C4—O2—C8112.02 (9)C17—C16—H16121.4
C6—O3—C9114.65 (9)C15—C16—H16121.4
C18—N1—C11111.94 (9)C16—C17—C12121.89 (11)
C18—N1—C10123.58 (9)C16—C17—C18130.24 (11)
C11—N1—C10123.92 (9)C12—C17—C18107.80 (10)
C27—N2—C20111.99 (9)O5—C18—N1124.86 (11)
C27—N2—C19123.90 (9)O5—C18—C17129.13 (11)
C20—N2—C19123.69 (10)N1—C18—C17105.96 (9)
C36—N3—C29112.05 (10)N2—C19—C3112.88 (9)
C36—N3—C28124.02 (10)N2—C19—H19A109.0
C29—N3—C28123.93 (10)C3—C19—H19A109.0
O3—C6—C5118.58 (10)N2—C19—H19B109.0
O3—C6—C1119.46 (10)C3—C19—H19B109.0
C5—C6—C1121.76 (10)H19A—C19—H19B107.8
C2—C1—C6117.61 (10)O6—C20—N2125.21 (11)
C2—C1—C10124.23 (9)O6—C20—C21129.24 (11)
C6—C1—C10118.13 (9)N2—C20—C21105.56 (10)
O1—C2—C1119.42 (9)C22—C21—C26121.27 (11)
O1—C2—C3118.54 (9)C22—C21—C20130.47 (11)
C1—C2—C3122.02 (10)C26—C21—C20108.25 (10)
C4—C3—C2117.75 (10)C21—C22—C23117.28 (12)
C4—C3—C19120.26 (10)C21—C22—H22121.4
C2—C3—C19121.96 (10)C23—C22—H22121.4
O2—C4—C5118.08 (10)C24—C23—C22121.47 (11)
O2—C4—C3119.75 (10)C24—C23—H23119.3
C5—C4—C3122.17 (10)C22—C23—H23119.3
C4—C5—C6118.20 (10)C23—C24—C25121.02 (12)
C4—C5—C28120.91 (10)C23—C24—H24119.5
C6—C5—C28120.86 (10)C25—C24—H24119.5
O1—C7—H7A109.5C26—C25—C24117.04 (12)
O1—C7—H7B109.5C26—C25—H25121.5
H7A—C7—H7B109.5C24—C25—H25121.5
O1—C7—H7C109.5C25—C26—C21121.89 (11)
H7A—C7—H7C109.5C25—C26—C27129.93 (11)
H7B—C7—H7C109.5C21—C26—C27108.15 (10)
O2—C8—H8A109.5O7—C27—N2125.44 (10)
O2—C8—H8B109.5O7—C27—C26128.63 (11)
H8A—C8—H8B109.5N2—C27—C26105.90 (9)
O2—C8—H8C109.5N3—C28—C5113.73 (9)
H8A—C8—H8C109.5N3—C28—H28A108.8
H8B—C8—H8C109.5C5—C28—H28A108.8
O3—C9—H9A109.5N3—C28—H28B108.8
O3—C9—H9B109.5C5—C28—H28B108.8
H9A—C9—H9B109.5H28A—C28—H28B107.7
O3—C9—H9C109.5O8—C29—N3125.31 (11)
H9A—C9—H9C109.5O8—C29—C30129.03 (11)
H9B—C9—H9C109.5N3—C29—C30105.65 (9)
N1—C10—C1115.94 (9)C31—C30—C35121.58 (11)
N1—C10—H10A108.3C31—C30—C29130.32 (10)
C1—C10—H10A108.3C35—C30—C29108.09 (10)
N1—C10—H10B108.3C30—C31—C32117.13 (11)
C1—C10—H10B108.3C30—C31—H31121.4
H10A—C10—H10B107.4C32—C31—H31121.4
O4—C11—N1125.15 (11)C31—C32—C33121.20 (12)
O4—C11—C12129.32 (11)C31—C32—H32119.4
N1—C11—C12105.53 (9)C33—C32—H32119.4
C13—C12—C17121.30 (11)C34—C33—C32120.69 (12)
C13—C12—C11130.13 (11)C34—C33—H33119.7
C17—C12—C11108.52 (10)C32—C33—H33119.7
C12—C13—C14117.29 (12)C35—C34—C33117.68 (12)
C12—C13—H13121.4C35—C34—H34121.2
C14—C13—H13121.4C33—C34—H34121.2
C15—C14—C13121.17 (12)C34—C35—C30121.68 (12)
C15—C14—H14119.4C34—C35—C36129.94 (11)
C13—C14—H14119.4C30—C35—C36108.36 (10)
C16—C15—C14121.15 (12)O9—C36—N3124.89 (12)
C16—C15—H15119.4O9—C36—C35129.29 (12)
C14—C15—H15119.4N3—C36—C35105.81 (10)
C9—O3—C6—C5104.74 (12)C20—N2—C19—C374.87 (13)
C9—O3—C6—C180.27 (13)C4—C3—C19—N2121.69 (11)
O3—C6—C1—C2178.55 (9)C2—C3—C19—N256.16 (14)
C5—C6—C1—C23.73 (16)C27—N2—C20—O6177.12 (11)
O3—C6—C1—C103.32 (15)C19—N2—C20—O64.32 (18)
C5—C6—C1—C10178.14 (10)C27—N2—C20—C212.87 (12)
C7—O1—C2—C1103.89 (11)C19—N2—C20—C21175.67 (9)
C7—O1—C2—C377.97 (12)O6—C20—C21—C221.0 (2)
C6—C1—C2—O1179.81 (9)N2—C20—C21—C22178.97 (11)
C10—C1—C2—O12.18 (15)O6—C20—C21—C26179.56 (12)
C6—C1—C2—C32.11 (15)N2—C20—C21—C260.44 (12)
C10—C1—C2—C3175.90 (10)C26—C21—C22—C231.46 (17)
O1—C2—C3—C4174.67 (9)C20—C21—C22—C23179.82 (11)
C1—C2—C3—C47.24 (15)C21—C22—C23—C240.08 (17)
O1—C2—C3—C197.44 (15)C22—C23—C24—C251.35 (18)
C1—C2—C3—C19170.66 (10)C23—C24—C25—C261.35 (17)
C8—O2—C4—C599.36 (12)C24—C25—C26—C210.03 (17)
C8—O2—C4—C381.54 (12)C24—C25—C26—C27177.75 (11)
C2—C3—C4—O2174.09 (9)C22—C21—C26—C251.47 (17)
C19—C3—C4—O27.98 (15)C20—C21—C26—C25179.84 (10)
C2—C3—C4—C56.85 (16)C22—C21—C26—C27176.74 (10)
C19—C3—C4—C5171.08 (10)C20—C21—C26—C271.95 (12)
O2—C4—C5—C6179.58 (9)C20—N2—C27—O7174.20 (11)
C3—C4—C5—C61.34 (16)C19—N2—C27—O71.42 (17)
O2—C4—C5—C281.27 (15)C20—N2—C27—C264.04 (12)
C3—C4—C5—C28179.66 (10)C19—N2—C27—C26176.82 (9)
O3—C6—C5—C4178.99 (10)C25—C26—C27—O73.5 (2)
C1—C6—C5—C44.12 (16)C21—C26—C27—O7174.53 (11)
O3—C6—C5—C280.68 (16)C25—C26—C27—N2178.36 (11)
C1—C6—C5—C28174.19 (10)C21—C26—C27—N23.63 (12)
C18—N1—C10—C181.93 (13)C36—N3—C28—C561.67 (15)
C11—N1—C10—C1107.26 (12)C29—N3—C28—C5117.70 (12)
C2—C1—C10—N142.09 (15)C4—C5—C28—N357.36 (15)
C6—C1—C10—N1139.92 (10)C6—C5—C28—N3124.37 (12)
C18—N1—C11—O4175.72 (11)C36—N3—C29—O8179.36 (12)
C10—N1—C11—O43.96 (18)C28—N3—C29—O80.08 (19)
C18—N1—C11—C123.69 (12)C36—N3—C29—C301.62 (13)
C10—N1—C11—C12175.45 (9)C28—N3—C29—C30178.94 (10)
O4—C11—C12—C131.2 (2)O8—C29—C30—C312.3 (2)
N1—C11—C12—C13178.18 (12)N3—C29—C30—C31176.70 (12)
O4—C11—C12—C17178.78 (12)O8—C29—C30—C35178.89 (13)
N1—C11—C12—C170.59 (12)N3—C29—C30—C352.13 (12)
C17—C12—C13—C141.78 (18)C35—C30—C31—C321.23 (17)
C11—C12—C13—C14179.10 (12)C29—C30—C31—C32179.92 (12)
C12—C13—C14—C150.01 (19)C30—C31—C32—C330.27 (18)
C13—C14—C15—C161.7 (2)C31—C32—C33—C341.2 (2)
C14—C15—C16—C171.49 (18)C32—C33—C34—C350.67 (19)
C15—C16—C17—C120.28 (17)C33—C34—C35—C300.82 (18)
C15—C16—C17—C18176.42 (11)C33—C34—C35—C36177.85 (12)
C13—C12—C17—C161.96 (18)C31—C30—C35—C341.83 (18)
C11—C12—C17—C16179.80 (10)C29—C30—C35—C34179.22 (11)
C13—C12—C17—C18175.39 (10)C31—C30—C35—C36177.10 (11)
C11—C12—C17—C182.45 (12)C29—C30—C35—C361.85 (13)
C11—N1—C18—O5172.43 (10)C29—N3—C36—O9179.40 (12)
C10—N1—C18—O50.64 (17)C28—N3—C36—O91.2 (2)
C11—N1—C18—C175.16 (12)C29—N3—C36—C350.52 (13)
C10—N1—C18—C17176.95 (9)C28—N3—C36—C35179.97 (10)
C16—C17—C18—O54.2 (2)C34—C35—C36—O90.9 (2)
C12—C17—C18—O5172.84 (11)C30—C35—C36—O9177.93 (13)
C16—C17—C18—N1178.34 (11)C34—C35—C36—N3179.69 (12)
C12—C17—C18—N14.60 (12)C30—C35—C36—N30.88 (13)
C27—N2—C19—C3113.18 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···O8i0.982.473.2068 (15)132
C8—H8B···O5i0.982.343.2920 (15)165
C9—H9A···O4ii0.982.563.4742 (15)156
C9—H9C···O90.982.383.2684 (19)151
C10—H10A···O40.992.542.9144 (14)102
C10—H10B···O30.992.322.8017 (15)109
C19—H19A···O70.992.542.9200 (15)103
C19—H19B···O20.992.362.8457 (14)109
C23—H23···O1iii0.952.453.3231 (16)153
C28—H28A···O80.992.522.9187 (16)103
C28—H28B···O30.992.342.8289 (16)109
C32—H32···O2iv0.952.563.2917 (16)134
C34—H34···O7v0.952.463.4066 (15)172
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+1, z; (iii) x+1, y+1, z; (iv) x+1, y, z+1; (v) x, y1, z.

Experimental details

Crystal data
Chemical formulaC36H27N3O9
Mr645.61
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)10.2370 (3), 10.3671 (3), 14.6501 (4)
α, β, γ (°)79.804 (1), 79.512 (1), 83.874 (1)
V3)1500.20 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.51 × 0.50 × 0.28
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.949, 0.971
No. of measured, independent and
observed [I > 2σ(I)] reflections
29692, 8026, 6992
Rint0.021
(sin θ/λ)max1)0.684
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.100, 0.96
No. of reflections8026
No. of parameters436
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.46, 0.35

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···O8i0.982.473.2068 (15)132.1
C8—H8B···O5i0.982.343.2920 (15)164.8
C9—H9A···O4ii0.982.563.4742 (15)155.8
C9—H9C···O90.982.383.2684 (19)150.8
C10—H10A···O40.992.542.9144 (14)102.0
C10—H10B···O30.992.322.8017 (15)108.7
C19—H19A···O70.992.542.9200 (15)102.7
C19—H19B···O20.992.362.8457 (14)109.1
C23—H23···O1iii0.952.453.3231 (16)152.8
C28—H28A···O80.992.522.9187 (16)103.4
C28—H28B···O30.992.342.8289 (16)109.2
C32—H32···O2iv0.952.563.2917 (16)134.0
C34—H34···O7v0.952.463.4066 (15)172.1
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+1, z; (iii) x+1, y+1, z; (iv) x+1, y, z+1; (v) x, y1, z.
 

References

First citationBruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationDesiraju, G. R. (2002). Acc. Chem. Res. 35, 565–573.  Web of Science CrossRef PubMed CAS
First citationDesiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond In Structural Chemistry and Biology. IUCR Monographs on Crystallography, Vol. 9. New York: Oxford University Press.
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationMazik, M. (2009). Chem. Soc. Rev. 38, 935–956.  Web of Science CrossRef PubMed CAS
First citationMazik, M., Bläser, D. & Boese, R. (2001). Tetrahedron, 57, 5791–5797.  Web of Science CSD CrossRef CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSteiner, T. (2002). Angew. Chem. Int. Ed. 41, 48–76.  Web of Science CrossRef CAS

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