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Acta Crystallogr Sect E Struct Rep Online. 2008 March 1; 64(Pt 3): o608.
Published online 2008 February 20. doi:  10.1107/S1600536808004510
PMCID: PMC2960883

2-(2-Benzyl­oxyphen­yl)-1H-benzimid­azole

Abstract

The asymmetric unit of the title compound, C20H16N2O, contains two mol­ecules. The dihedral angles between the benzimidazole ring systems and the attached benzene rings are 10.6 (5) and 13.7 (5)°. The conformers are linked by bifurcated three-centre hydrogen bonds, forming chains along the diagonal of the a b plane. The packing is further stabilized by π–π and C—H(...)π inter­actions.

Related literature

For general background, see: Desiraju & Steiner (1999 [triangle]); Lehn (1990 [triangle]); Saenger (1984 [triangle]); Wakelin (1986 [triangle]). For related structures, see: Estrada-Soto et al. (2006 [triangle]); Moreno-Diaz et al. (2006 [triangle]); Navarrete-Vázquez et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o608-scheme1.jpg

Experimental

Crystal data

  • C20H16N2O
  • M r = 300.35
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o608-efi1.jpg
  • a = 11.526 (2) Å
  • b = 17.210 (3) Å
  • c = 15.866 (3) Å
  • β = 90.52 (3)°
  • V = 3147.0 (11) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 (2) K
  • 0.31 × 0.21 × 0.17 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003 [triangle]) T min = 0.976, T max = 0.987
  • 7808 measured reflections
  • 2830 independent reflections
  • 2691 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.100
  • S = 1.17
  • 2830 reflections
  • 423 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT-Plus NT (Bruker, 2001 [triangle]); data reduction: SAINT-Plus NT; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004510/sj2464sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004510/sj2464Isup2.hkl

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

Acknowledgments

This work was supported by the Consejo Nacional de Ciencia y Tecnología (CONACyT) under grant Nos. 3562P-E and PROMEP-SEP UAEMOR-PTC-131 (GNV).

supplementary crystallographic information

Comment

Hydrogen bonding and π–π interactions are among the principal forces which determine the intercalation of drugs into DNA (Saenger, 1984; Wakelin, 1986), together with self-assembly and recognition in some chemical and biological systems (Lehn, 1990). Recently, we have reported the synthesis of a small library of 2-arylbenzimidazole compounds that show spasmolytic and relaxant activity (Moreno-Diaz et al., 2006; Navarrete-Vázquez et al., 2006; Estrada-Soto et al., 2006). In order to extend our research on the relationship between the structure of benzimidazole derivatives and their pharmacological activity we have determined the crystal structure of (I).

The asymmetric unit of (I) contains two conformers (Ia, Ib) (Fig. 1). Bond lengths between equivalent non-H atoms of each conformer are similar, with differences less than 3 s.u. The dihedral angles between the benzimidazole ring systems and the 2-benzyloxyphenyl substituents in Ia and Ib are 10.6 (5) and 13.7 (5)°, respectively. Both molecules display bifurcated N—H···N and N—H···O hydrogen bonds, Table 1 (Desiraju & Steiner, 1999). These hydrogen bonds interconnect molecules into chains running between the a and b axes (Fig. 2). Packing is further stabilized by C—H···π interactions involving the methylene H atoms on C14 of molecule Ia with the C27N4C26C21N3 benzimidazole ring (centroid Cg1) and the C28–C33 benzene ring (centroid Cg4) of two adjacent molecules of Ib (Fig. 3, Table 1). In the crystal packing there are also π–π interactions between adjacent molecules Ia and Ib, with a distance between the centroids of the C15–C20 (Cg3) and C28–C33 (Cg2) benzene rings of 3.859 (2) Å (Fig. 3, Table 1). In conclusion, this crystal structure illustrates four types of cooperative intra and intermolecular interactions: offset π–π stacking and C—H···π interactions as well as classical N—H···N and N—H···O hydrogen bonds.

Experimental

The title compound, (I), was synthesized according to the method of Moreno-Diaz et al. (2006). Single crystals of (I) were obtained from methanol with yield 2.07 g, 75%.

Refinement

Aromatic and methylene H atoms were positioned geometrically, were constrained to the riding-model approximation [C—Haryl = 0.93 Å, Uiso(Haryl) = 1.2Ueq(Caryl); C—Hmethylene = 0.97 Å, a Uiso(Hmethylene) = 1.5 Ueq(Cmethylene)]. Atoms H1 and H3A, which are involved in hydrogen-bonding interactions, were located in a difference Fourier map and refined freely with isotropic displacement parameters. In the absence of significant anomalous dispersion effects, Friedel pairs were averaged.

Figures

Fig. 1.
The asymmetric unit of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
Fig. 2.
A view of the crystal packing of (I), showing the formation of chains. Hydrogen bonds are represented by dotted lines and H atoms not involved in hydrogen bonding have been omitted for clarity.
Fig. 3.
View of the offset π–π interactions and the C–H···π-facial hydrogen bonds between methylene group of Ia and the imidazole and aryl rings of Ib. Dashed lines indicate the vectors between C14 ...

Crystal data

C20H16N2OF000 = 1264
Mr = 300.35Dx = 1.268 Mg m3
Monoclinic, CcMelting point: 415.5 K
Hall symbol: C -2ycMo Kα radiation λ = 0.71073 Å
a = 11.526 (2) ÅCell parameters from 68 reflections
b = 17.210 (3) Åθ = 2.6–25.2º
c = 15.866 (3) ŵ = 0.08 mm1
β = 90.52 (3)ºT = 293 (2) K
V = 3147.0 (11) Å3Rectangular, colourless
Z = 80.31 × 0.21 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer2830 independent reflections
Radiation source: fine-focus sealed tube2691 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.038
Detector resolution: 8.3 pixels mm-1θmax = 25.2º
T = 293(2) Kθmin = 2.1º
[var phi] and ω scansh = −13→13
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)k = −20→11
Tmin = 0.976, Tmax = 0.987l = −19→16
7808 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)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100  w = 1/[σ2(Fo2) + (0.0376P)2 + 0.4648P] where P = (Fo2 + 2Fc2)/3
S = 1.17(Δ/σ)max < 0.001
2830 reflectionsΔρmax = 0.20 e Å3
423 parametersΔρmin = −0.20 e Å3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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
C10.0469 (3)0.1160 (2)0.3249 (2)0.0179 (8)
C2−0.0279 (3)0.1316 (2)0.3917 (2)0.0213 (8)
H2−0.07550.17520.39200.026*
C3−0.0273 (3)0.0789 (2)0.4571 (2)0.0234 (8)
H3−0.07350.08800.50380.028*
C40.0419 (3)0.0115 (2)0.4547 (2)0.0243 (9)
H40.0389−0.02340.49940.029*
C50.1134 (3)−0.0040 (2)0.3885 (2)0.0241 (9)
H50.1589−0.04860.38780.029*
C60.1160 (3)0.0492 (2)0.3217 (2)0.0176 (8)
C70.1528 (3)0.1149 (2)0.2093 (2)0.0161 (7)
C80.2074 (3)0.1393 (2)0.1295 (2)0.0175 (8)
C90.1951 (3)0.2138 (2)0.0950 (2)0.0183 (8)
C100.2567 (3)0.2342 (2)0.0234 (2)0.0251 (9)
H100.25010.28400.00120.030*
C110.3279 (3)0.1801 (2)−0.0149 (2)0.0250 (9)
H110.36930.1943−0.06250.030*
C120.3387 (3)0.1057 (2)0.0163 (2)0.0254 (9)
H120.38540.0694−0.01070.031*
C130.2787 (3)0.0857 (2)0.0886 (2)0.0219 (8)
H130.28600.03570.11030.026*
C140.1043 (3)0.3400 (2)0.1037 (2)0.0219 (8)
H14A0.03190.36040.12520.026*
H14B0.09760.33800.04270.026*
C150.2018 (3)0.3952 (2)0.1275 (2)0.0199 (8)
C160.2041 (3)0.4669 (2)0.0885 (2)0.0229 (8)
H160.14730.47960.04880.027*
C170.2905 (3)0.5204 (2)0.1082 (2)0.0260 (9)
H170.29180.56840.08130.031*
C180.3752 (4)0.5020 (2)0.1683 (2)0.0294 (9)
H180.43340.53740.18180.035*
C190.3714 (3)0.4304 (2)0.2071 (2)0.0276 (9)
H190.42720.41800.24760.033*
C200.2863 (3)0.3768 (2)0.1872 (2)0.0234 (9)
H200.28560.32860.21360.028*
C210.7495 (3)0.6470 (2)0.7012 (2)0.0180 (8)
C220.6466 (3)0.6399 (2)0.6541 (2)0.0224 (8)
H220.61030.59220.64630.027*
C230.6018 (3)0.7076 (2)0.6200 (2)0.0268 (9)
H230.53310.70540.58890.032*
C240.6575 (4)0.7794 (2)0.6310 (2)0.0274 (9)
H240.62570.82350.60620.033*
C250.7588 (3)0.7861 (2)0.6781 (2)0.0237 (9)
H250.79430.83400.68650.028*
C260.8057 (3)0.7180 (2)0.7126 (2)0.0191 (8)
C270.9128 (3)0.6312 (2)0.7734 (2)0.0183 (8)
C281.0124 (3)0.5952 (2)0.8170 (2)0.0196 (8)
C291.0358 (3)0.5147 (2)0.8146 (2)0.0238 (8)
C301.1374 (3)0.4861 (2)0.8502 (2)0.0270 (9)
H301.15330.43320.84800.032*
C311.2149 (3)0.5359 (3)0.8887 (2)0.0301 (10)
H311.28360.51640.91150.036*
C321.1918 (3)0.6145 (3)0.8941 (2)0.0308 (10)
H321.24370.64730.92170.037*
C331.0913 (3)0.6440 (2)0.8583 (2)0.0247 (9)
H331.07610.69700.86180.030*
C340.9791 (4)0.3883 (2)0.7630 (2)0.0288 (9)
H34A1.05960.38280.74680.035*
H34B0.93140.36860.71710.035*
C350.9579 (3)0.3394 (2)0.8407 (2)0.0232 (8)
C360.8786 (4)0.3607 (2)0.9019 (3)0.0324 (10)
H360.83900.40760.89700.039*
C370.8581 (4)0.3123 (3)0.9702 (3)0.0367 (11)
H370.80490.32711.01100.044*
C380.9165 (4)0.2422 (3)0.9780 (3)0.0320 (10)
H380.90330.21021.02410.038*
C390.9938 (4)0.2205 (2)0.9173 (3)0.0321 (10)
H391.03200.17310.92210.039*
C401.0159 (3)0.2682 (2)0.8486 (2)0.0260 (9)
H401.06890.25280.80800.031*
N10.0711 (3)0.15646 (17)0.25172 (18)0.0174 (6)
N20.1813 (3)0.04949 (17)0.24872 (17)0.0191 (7)
N30.8195 (3)0.59233 (18)0.74010 (19)0.0197 (7)
N40.9075 (3)0.70755 (17)0.75867 (17)0.0180 (7)
O10.1204 (2)0.26267 (14)0.13499 (15)0.0230 (6)
O20.9538 (2)0.46984 (15)0.77489 (16)0.0266 (6)
H10.038 (3)0.202 (2)0.241 (2)0.015 (9)*
H3A0.807 (4)0.545 (3)0.740 (3)0.034 (12)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.022 (2)0.0171 (18)0.0143 (17)−0.0041 (16)−0.0013 (14)0.0012 (14)
C20.022 (2)0.0161 (18)0.026 (2)−0.0017 (16)0.0013 (15)0.0000 (16)
C30.024 (2)0.027 (2)0.0197 (18)−0.0024 (17)0.0014 (15)−0.0030 (17)
C40.032 (2)0.023 (2)0.0186 (18)−0.0037 (18)−0.0018 (16)0.0068 (15)
C50.028 (2)0.0168 (19)0.027 (2)−0.0005 (17)−0.0035 (16)0.0012 (17)
C60.018 (2)0.0155 (18)0.0189 (18)−0.0015 (15)−0.0006 (15)−0.0024 (15)
C70.0180 (19)0.0121 (18)0.0182 (17)−0.0026 (15)−0.0024 (14)−0.0031 (14)
C80.0142 (18)0.0204 (19)0.0179 (17)−0.0069 (15)−0.0038 (14)−0.0025 (15)
C90.021 (2)0.0167 (18)0.0170 (18)0.0002 (16)−0.0015 (15)−0.0009 (15)
C100.029 (2)0.020 (2)0.026 (2)−0.0009 (18)−0.0023 (16)0.0019 (17)
C110.027 (2)0.028 (2)0.0198 (19)−0.0064 (18)0.0087 (16)−0.0008 (16)
C120.028 (2)0.024 (2)0.0248 (19)0.0042 (18)0.0069 (16)−0.0085 (17)
C130.023 (2)0.0181 (19)0.0249 (19)0.0030 (17)−0.0031 (15)−0.0018 (16)
C140.027 (2)0.0172 (19)0.0217 (19)0.0021 (17)0.0031 (15)0.0033 (16)
C150.023 (2)0.019 (2)0.0179 (18)0.0047 (16)0.0056 (15)−0.0003 (15)
C160.028 (2)0.0211 (19)0.0199 (18)0.0051 (17)−0.0026 (16)−0.0024 (16)
C170.035 (2)0.018 (2)0.026 (2)0.0010 (18)0.0052 (17)−0.0031 (16)
C180.031 (2)0.030 (2)0.027 (2)−0.0011 (19)0.0056 (17)−0.0133 (18)
C190.018 (2)0.040 (2)0.025 (2)0.0062 (18)−0.0013 (15)−0.0056 (18)
C200.024 (2)0.025 (2)0.0206 (19)0.0045 (17)0.0041 (16)0.0008 (16)
C210.0165 (19)0.0150 (17)0.0225 (18)−0.0006 (15)0.0019 (14)0.0017 (15)
C220.022 (2)0.0182 (19)0.0270 (19)−0.0031 (16)−0.0006 (15)0.0009 (16)
C230.021 (2)0.028 (2)0.032 (2)0.0030 (18)−0.0043 (16)0.0006 (18)
C240.036 (2)0.023 (2)0.024 (2)0.0075 (18)0.0045 (17)0.0053 (17)
C250.029 (2)0.0189 (19)0.023 (2)−0.0057 (17)0.0084 (16)0.0035 (16)
C260.020 (2)0.0211 (19)0.0163 (17)−0.0003 (16)0.0039 (14)−0.0010 (15)
C270.0184 (19)0.0175 (18)0.0191 (17)−0.0065 (16)0.0060 (14)−0.0012 (15)
C280.0171 (19)0.0230 (19)0.0186 (17)−0.0029 (17)0.0068 (14)−0.0019 (16)
C290.026 (2)0.027 (2)0.0177 (18)0.0016 (18)0.0014 (15)−0.0022 (17)
C300.027 (2)0.029 (2)0.0249 (19)0.0037 (18)−0.0020 (16)0.0024 (18)
C310.018 (2)0.048 (3)0.024 (2)0.001 (2)−0.0043 (16)0.012 (2)
C320.027 (2)0.041 (3)0.024 (2)−0.0114 (19)−0.0042 (17)0.0071 (19)
C330.022 (2)0.029 (2)0.0226 (18)−0.0045 (18)0.0018 (16)0.0004 (17)
C340.032 (2)0.023 (2)0.031 (2)0.0075 (19)−0.0077 (18)−0.0064 (17)
C350.020 (2)0.024 (2)0.026 (2)−0.0005 (16)−0.0070 (16)−0.0040 (16)
C360.024 (2)0.030 (2)0.044 (2)0.0056 (19)−0.0039 (19)−0.007 (2)
C370.023 (2)0.053 (3)0.034 (2)−0.014 (2)0.0047 (18)−0.009 (2)
C380.033 (3)0.029 (2)0.034 (2)−0.016 (2)−0.0012 (19)0.0032 (19)
C390.033 (2)0.023 (2)0.040 (2)−0.0030 (19)−0.0056 (19)−0.0005 (19)
C400.025 (2)0.025 (2)0.029 (2)0.0021 (18)0.0007 (16)−0.0053 (18)
N10.0187 (17)0.0113 (15)0.0222 (16)0.0033 (13)0.0026 (12)0.0008 (13)
N20.0202 (17)0.0152 (15)0.0219 (16)0.0006 (13)−0.0023 (13)−0.0016 (13)
N30.0213 (17)0.0133 (16)0.0244 (16)−0.0015 (14)−0.0008 (13)0.0004 (14)
N40.0190 (16)0.0200 (15)0.0149 (15)−0.0029 (14)0.0011 (12)−0.0004 (12)
O10.0251 (14)0.0162 (13)0.0279 (14)0.0043 (12)0.0073 (11)0.0033 (11)
O20.0246 (15)0.0203 (14)0.0346 (15)0.0045 (12)−0.0103 (12)−0.0028 (12)

Geometric parameters (Å, °)

C1—N11.384 (4)C21—C261.394 (5)
C1—C21.399 (5)C21—C221.401 (5)
C1—C61.400 (5)C22—C231.382 (5)
C2—C31.378 (5)C22—H220.9300
C2—H20.9300C23—C241.403 (6)
C3—C41.408 (5)C23—H230.9300
C3—H30.9300C24—C251.385 (5)
C4—C51.367 (5)C24—H240.9300
C4—H40.9300C25—C261.399 (5)
C5—C61.401 (5)C25—H250.9300
C5—H50.9300C26—N41.388 (4)
C6—N21.387 (4)C27—N41.335 (4)
C7—N21.327 (4)C27—N31.368 (4)
C7—N11.365 (4)C27—C281.472 (5)
C7—C81.480 (5)C28—C331.398 (5)
C8—C131.399 (5)C28—C291.412 (5)
C8—C91.402 (5)C29—O21.370 (4)
C9—O11.365 (4)C29—C301.386 (5)
C9—C101.390 (5)C30—C311.376 (5)
C10—C111.384 (5)C30—H300.9300
C10—H100.9300C31—C321.381 (6)
C11—C121.379 (5)C31—H310.9300
C11—H110.9300C32—C331.382 (5)
C12—C131.389 (5)C32—H320.9300
C12—H120.9300C33—H330.9300
C13—H130.9300C34—O21.447 (4)
C14—O11.431 (4)C34—C351.514 (5)
C14—C151.517 (5)C34—H34A0.9700
C14—H14A0.9700C34—H34B0.9700
C14—H14B0.9700C35—C361.388 (5)
C15—C161.382 (5)C35—C401.401 (5)
C15—C201.388 (5)C36—C371.389 (6)
C16—C171.389 (5)C36—H360.9300
C16—H160.9300C37—C381.387 (6)
C17—C181.395 (5)C37—H370.9300
C17—H170.9300C38—C391.370 (6)
C18—C191.378 (6)C38—H380.9300
C18—H180.9300C39—C401.390 (6)
C19—C201.381 (5)C39—H390.9300
C19—H190.9300C40—H400.9300
C20—H200.9300N1—H10.89 (4)
C21—N31.382 (5)N3—H3A0.83 (4)
N1—C1—C2132.0 (3)C21—C22—H22121.8
N1—C1—C6105.3 (3)C22—C23—C24121.7 (4)
C2—C1—C6122.6 (3)C22—C23—H23119.2
C3—C2—C1116.4 (4)C24—C23—H23119.2
C3—C2—H2121.8C25—C24—C23121.5 (4)
C1—C2—H2121.8C25—C24—H24119.2
C2—C3—C4121.4 (4)C23—C24—H24119.2
C2—C3—H3119.3C24—C25—C26117.5 (3)
C4—C3—H3119.3C24—C25—H25121.2
C5—C4—C3121.8 (3)C26—C25—H25121.2
C5—C4—H4119.1N4—C26—C21110.2 (3)
C3—C4—H4119.1N4—C26—C25129.5 (3)
C4—C5—C6118.1 (3)C21—C26—C25120.3 (3)
C4—C5—H5121.0N4—C27—N3112.3 (3)
C6—C5—H5121.0N4—C27—C28122.0 (3)
N2—C6—C1109.9 (3)N3—C27—C28125.6 (3)
N2—C6—C5130.5 (3)C33—C28—C29118.6 (4)
C1—C6—C5119.6 (3)C33—C28—C27117.9 (3)
N2—C7—N1112.4 (3)C29—C28—C27123.3 (3)
N2—C7—C8122.6 (3)O2—C29—C30124.4 (3)
N1—C7—C8125.0 (3)O2—C29—C28115.7 (3)
C13—C8—C9118.7 (3)C30—C29—C28119.9 (4)
C13—C8—C7117.8 (3)C31—C30—C29120.2 (4)
C9—C8—C7123.5 (3)C31—C30—H30119.9
O1—C9—C10123.7 (3)C29—C30—H30119.9
O1—C9—C8116.3 (3)C30—C31—C32120.8 (4)
C10—C9—C8120.0 (3)C30—C31—H31119.6
C11—C10—C9119.9 (3)C32—C31—H31119.6
C11—C10—H10120.1C31—C32—C33119.8 (4)
C9—C10—H10120.1C31—C32—H32120.1
C12—C11—C10121.3 (3)C33—C32—H32120.1
C12—C11—H11119.3C32—C33—C28120.7 (4)
C10—C11—H11119.3C32—C33—H33119.7
C11—C12—C13118.8 (4)C28—C33—H33119.7
C11—C12—H12120.6O2—C34—C35113.5 (3)
C13—C12—H12120.6O2—C34—H34A108.9
C12—C13—C8121.3 (3)C35—C34—H34A108.9
C12—C13—H13119.4O2—C34—H34B108.9
C8—C13—H13119.4C35—C34—H34B108.9
O1—C14—C15113.7 (3)H34A—C34—H34B107.7
O1—C14—H14A108.8C36—C35—C40119.1 (4)
C15—C14—H14A108.8C36—C35—C34122.3 (3)
O1—C14—H14B108.8C40—C35—C34118.6 (3)
C15—C14—H14B108.8C35—C36—C37120.3 (4)
H14A—C14—H14B107.7C35—C36—H36119.9
C16—C15—C20119.5 (4)C37—C36—H36119.9
C16—C15—C14117.7 (3)C38—C37—C36120.4 (4)
C20—C15—C14122.8 (3)C38—C37—H37119.8
C15—C16—C17120.5 (3)C36—C37—H37119.8
C15—C16—H16119.7C39—C38—C37119.6 (4)
C17—C16—H16119.7C39—C38—H38120.2
C16—C17—C18120.0 (4)C37—C38—H38120.2
C16—C17—H17120.0C38—C39—C40121.0 (4)
C18—C17—H17120.0C38—C39—H39119.5
C19—C18—C17118.9 (4)C40—C39—H39119.5
C19—C18—H18120.6C39—C40—C35119.7 (4)
C17—C18—H18120.6C39—C40—H40120.1
C18—C19—C20121.3 (4)C35—C40—H40120.1
C18—C19—H19119.3C7—N1—C1107.1 (3)
C20—C19—H19119.3C7—N1—H1131 (2)
C19—C20—C15119.8 (4)C1—N1—H1121 (2)
C19—C20—H20120.1C7—N2—C6105.3 (3)
C15—C20—H20120.1C27—N3—C21107.0 (3)
N3—C21—C26105.6 (3)C27—N3—H3A128 (3)
N3—C21—C22131.8 (3)C21—N3—H3A125 (3)
C26—C21—C22122.5 (3)C27—N4—C26104.9 (3)
C23—C22—C21116.5 (3)C9—O1—C14119.4 (3)
C23—C22—H22121.8C29—O2—C34117.9 (3)
N1—C1—C2—C3−177.8 (4)N4—C27—C28—C3312.9 (5)
C6—C1—C2—C32.5 (5)N3—C27—C28—C33−170.4 (3)
C1—C2—C3—C4−2.4 (5)N4—C27—C28—C29−163.0 (3)
C2—C3—C4—C51.4 (6)N3—C27—C28—C2913.7 (5)
C3—C4—C5—C6−0.3 (5)C33—C28—C29—O2178.5 (3)
N1—C1—C6—N20.5 (4)C27—C28—C29—O2−5.7 (5)
C2—C1—C6—N2−179.7 (3)C33—C28—C29—C30−2.3 (5)
N1—C1—C6—C5178.7 (3)C27—C28—C29—C30173.6 (3)
C2—C1—C6—C5−1.5 (5)O2—C29—C30—C31180.0 (4)
C4—C5—C6—N2178.2 (4)C28—C29—C30—C310.8 (5)
C4—C5—C6—C10.4 (5)C29—C30—C31—C321.3 (6)
N2—C7—C8—C139.5 (5)C30—C31—C32—C33−1.8 (6)
N1—C7—C8—C13−172.1 (3)C31—C32—C33—C280.2 (6)
N2—C7—C8—C9−167.8 (3)C29—C28—C33—C321.8 (5)
N1—C7—C8—C910.6 (5)C27—C28—C33—C32−174.3 (3)
C13—C8—C9—O1177.0 (3)O2—C34—C35—C3626.2 (5)
C7—C8—C9—O1−5.7 (5)O2—C34—C35—C40−157.3 (3)
C13—C8—C9—C10−2.5 (5)C40—C35—C36—C370.6 (6)
C7—C8—C9—C10174.8 (3)C34—C35—C36—C37177.1 (4)
O1—C9—C10—C11−177.9 (3)C35—C36—C37—C38−0.1 (6)
C8—C9—C10—C111.6 (5)C36—C37—C38—C39−0.7 (6)
C9—C10—C11—C120.5 (6)C37—C38—C39—C401.0 (6)
C10—C11—C12—C13−1.5 (6)C38—C39—C40—C35−0.4 (6)
C11—C12—C13—C80.5 (6)C36—C35—C40—C39−0.4 (5)
C9—C8—C13—C121.5 (5)C34—C35—C40—C39−176.9 (3)
C7—C8—C13—C12−176.0 (3)N2—C7—N1—C11.5 (4)
O1—C14—C15—C16169.2 (3)C8—C7—N1—C1−177.0 (3)
O1—C14—C15—C20−11.9 (5)C2—C1—N1—C7179.1 (4)
C20—C15—C16—C170.5 (5)C6—C1—N1—C7−1.2 (4)
C14—C15—C16—C17179.4 (3)N1—C7—N2—C6−1.2 (4)
C15—C16—C17—C18−0.6 (5)C8—C7—N2—C6177.4 (3)
C16—C17—C18—C190.0 (5)C1—C6—N2—C70.4 (4)
C17—C18—C19—C200.6 (6)C5—C6—N2—C7−177.6 (4)
C18—C19—C20—C15−0.7 (5)N4—C27—N3—C210.1 (4)
C16—C15—C20—C190.2 (5)C28—C27—N3—C21−176.8 (3)
C14—C15—C20—C19−178.7 (3)C26—C21—N3—C270.4 (4)
N3—C21—C22—C23−176.6 (4)C22—C21—N3—C27176.7 (4)
C26—C21—C22—C23−0.9 (5)N3—C27—N4—C26−0.6 (4)
C21—C22—C23—C240.8 (6)C28—C27—N4—C26176.5 (3)
C22—C23—C24—C25−1.3 (6)C21—C26—N4—C270.9 (4)
C23—C24—C25—C261.7 (5)C25—C26—N4—C27−177.9 (4)
N3—C21—C26—N4−0.8 (4)C10—C9—O1—C14−1.1 (5)
C22—C21—C26—N4−177.6 (3)C8—C9—O1—C14179.4 (3)
N3—C21—C26—C25178.1 (3)C15—C14—O1—C9−78.0 (4)
C22—C21—C26—C251.4 (5)C30—C29—O2—C34−5.5 (5)
C24—C25—C26—N4176.9 (3)C28—C29—O2—C34173.7 (3)
C24—C25—C26—C21−1.7 (5)C35—C34—O2—C2980.6 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O10.89 (4)2.20 (3)2.667 (4)112 (3)
N1—H1···N4i0.89 (4)2.18 (3)3.008 (4)154 (3)
N3—H3A···O20.83 (4)2.20 (5)2.670 (4)117 (4)
N3—H3A···N2ii0.83 (4)2.18 (5)2.918 (4)148 (4)
C14—H14A···Cg1i0.972.883.736 (4)148
C14—H14B···Cg4iii0.972.923.721 (4)141
Cg3—···.Cg2i..3.859 (2).

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2464).

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