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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o400.
Published online 2009 January 28. doi:  10.1107/S1600536809002827
PMCID: PMC2968319

3-(1H-Benzimidazol-2-yl)-2-chloro-8-methyl­quinoline

Abstract

Two independent mol­ecules of the title compound, C17H12ClN3, are present in the structure. The angle between the planes defined by the atoms of the benzimidazole unit and the quinoline unit are 45.2 (3) and 44.0 (3)°, indicating an essentially identical conformation for both mol­ecules. Each of the independent mol­ecules is linked with a symmetry equivalent by an inter­molecular N—H(...)N hydrogen bond involving the two benzimidazole N atoms, to form chains in the crystallographic c direction.

Related literature

A closely related structure is reported by Rominger et al. (2009 [triangle]). An analogous pyridine compound is essentially flat (Kim et al., 2005 [triangle]).

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Object name is e-65-0o400-scheme1.jpg

Experimental

Crystal data

  • C17H12ClN3
  • M r = 293.75
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o400-efi1.jpg
  • a = 16.4721 (15) Å
  • b = 9.0061 (8) Å
  • c = 9.6643 (9) Å
  • β = 98.433 (2)°
  • V = 1418.2 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 200 (2) K
  • 0.41 × 0.16 × 0.11 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008b [triangle]) T min = 0.897, T max = 0.969
  • 14446 measured reflections
  • 6767 independent reflections
  • 6457 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.100
  • S = 1.12
  • 6767 reflections
  • 381 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.22 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 3244 Friedel pairs
  • Flack parameter: −0.03 (5)

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002827/fj2183sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002827/fj2183Isup2.hkl

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

supplementary crystallographic information

Refinement

For all hydrogen atoms the positions were calculated according to geometrical criteria. Planar geometry was assumed for the nitrogen atom of the benzimidazol unit. During the refinement the hydrogen atoms were allowed to shift with the preceding atoms. In the case of the methyl groups the torsion angles were allowed to refine. The isotropic displacement parameters were set as 1.2 times (1.5 for methyl) the equivalent isotropic displacement parameters of the preceding atoms.

Figures

Fig. 1.
Thermal ellipsoid representation of the title compound with displacement ellipsoids plotted at 50% probability level. Only one of the two independent molecules is shown.
Fig. 2.
Ball and stick representation of the hydrogen bond connected chain along the c direction. Hydrogen atoms not involved in hydrogen bonds (dashed lines) have been omitted. Each of the two independent molecules forms such an assembly, the analogous chain ...
Fig. 3.
Enhanced figure of both independent molecules of the title compound with displacement ellipsoids plotted at 50% probability level.

Crystal data

C17H12ClN3F(000) = 608
Mr = 293.75Dx = 1.376 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 5811 reflections
a = 16.4721 (15) Åθ = 2.5–28.2°
b = 9.0061 (8) ŵ = 0.27 mm1
c = 9.6643 (9) ÅT = 200 K
β = 98.433 (2)°Polyhedron, colourless
V = 1418.2 (2) Å30.41 × 0.16 × 0.11 mm
Z = 4

Data collection

Bruker APEX diffractometer6767 independent reflections
Radiation source: fine-focus sealed tube6457 reflections with I > 2σ(I)
graphiteRint = 0.025
ω scansθmax = 28.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b)h = −21→21
Tmin = 0.897, Tmax = 0.969k = −11→12
14446 measured reflectionsl = −12→12

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.100w = 1/[σ2(Fo2) + (0.0479P)2 + 0.2051P] where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max = 0.001
6767 reflectionsΔρmax = 0.33 e Å3
381 parametersΔρmin = −0.22 e Å3
2 restraintsAbsolute structure: Flack (1983), 3233 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.03 (5)

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
Cl10.05087 (4)1.03625 (6)−0.15249 (6)0.03642 (14)
N10.02863 (11)0.7608 (2)−0.1012 (2)0.0295 (4)
C20.07851 (13)0.8696 (2)−0.0672 (2)0.0263 (4)
C30.15072 (13)0.8633 (2)0.0341 (2)0.0244 (4)
C40.16618 (14)0.7291 (2)0.0999 (2)0.0306 (5)
H40.21270.71900.17000.037*
C50.11470 (15)0.6067 (2)0.0658 (2)0.0322 (5)
C60.12919 (17)0.4661 (3)0.1294 (3)0.0405 (6)
H60.17540.45080.19910.049*
C70.0760 (2)0.3524 (3)0.0897 (3)0.0472 (7)
H70.08600.25710.13080.057*
C80.00720 (19)0.3748 (3)−0.0107 (3)0.0457 (6)
H8−0.02920.2940−0.03440.055*
C9−0.01022 (16)0.5079 (3)−0.0765 (3)0.0382 (5)
C100.04522 (14)0.6272 (2)−0.0366 (2)0.0304 (5)
C11−0.08315 (19)0.5301 (4)−0.1860 (3)0.0526 (8)
H11A−0.06550.5316−0.27860.079*
H11B−0.10970.6246−0.16970.079*
H11C−0.12210.4485−0.18170.079*
C120.20363 (13)0.9916 (2)0.0744 (2)0.0230 (4)
N130.23031 (11)1.02682 (19)0.20545 (18)0.0253 (4)
N140.22948 (11)1.08601 (19)−0.01916 (17)0.0248 (3)
H140.21841.0802−0.11090.030*
C210.27661 (12)1.1546 (2)0.1966 (2)0.0239 (4)
C220.31876 (14)1.2431 (3)0.3023 (2)0.0313 (5)
H220.31911.21940.39820.038*
C230.35963 (15)1.3654 (3)0.2630 (2)0.0368 (5)
H230.38961.42590.33320.044*
C240.35834 (15)1.4032 (3)0.1227 (3)0.0364 (5)
H240.38691.48910.09950.044*
C250.31608 (15)1.3176 (3)0.0163 (2)0.0327 (5)
H250.31441.3434−0.07940.039*
C260.27646 (13)1.1928 (2)0.0567 (2)0.0252 (4)
Cl1B0.75134 (3)0.47673 (6)0.52013 (5)0.03402 (13)
N1B0.77153 (12)0.7516 (2)0.58632 (19)0.0286 (4)
C2B0.72268 (13)0.6411 (2)0.5955 (2)0.0254 (4)
C3B0.65160 (13)0.6429 (2)0.6622 (2)0.0244 (4)
C4B0.63496 (14)0.7753 (2)0.7222 (2)0.0298 (5)
H4B0.58870.78250.77010.036*
C5B0.68484 (14)0.9000 (2)0.7145 (2)0.0292 (4)
C6B0.66884 (16)1.0405 (3)0.7716 (3)0.0378 (5)
H6B0.62311.05310.81990.045*
C7B0.71925 (17)1.1565 (3)0.7568 (3)0.0405 (6)
H7B0.70821.25090.79370.049*
C8B0.78792 (16)1.1379 (3)0.6871 (3)0.0393 (6)
H8B0.82271.22080.67940.047*
C9B0.80661 (15)1.0060 (3)0.6302 (2)0.0341 (5)
C10B0.75394 (13)0.8840 (2)0.6439 (2)0.0281 (4)
C11B0.87946 (19)0.9877 (3)0.5563 (3)0.0473 (7)
H11D0.90761.08330.55340.071*
H11E0.86150.95290.46070.071*
H11F0.91720.91500.60630.071*
C12B0.59921 (13)0.5128 (2)0.6756 (2)0.0238 (4)
N13B0.57193 (11)0.4767 (2)0.79249 (18)0.0252 (4)
N14B0.57387 (11)0.4184 (2)0.56856 (17)0.0271 (4)
H14B0.58530.42460.48260.033*
C21B0.52618 (12)0.3494 (2)0.7604 (2)0.0243 (4)
C22B0.48330 (14)0.2607 (3)0.8442 (2)0.0318 (5)
H22B0.48240.28400.93980.038*
C23B0.44264 (15)0.1387 (3)0.7833 (2)0.0365 (5)
H23B0.41250.07790.83780.044*
C24B0.44435 (15)0.1015 (3)0.6433 (3)0.0367 (5)
H24B0.41570.01580.60520.044*
C25B0.48679 (15)0.1867 (3)0.5596 (2)0.0330 (5)
H25B0.48850.16130.46460.040*
C26B0.52677 (12)0.3110 (2)0.6203 (2)0.0245 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0340 (3)0.0292 (3)0.0432 (3)0.0011 (2)−0.0042 (2)0.0066 (2)
N10.0286 (9)0.0294 (9)0.0306 (9)−0.0025 (7)0.0045 (7)−0.0048 (7)
C20.0310 (11)0.0228 (10)0.0258 (10)0.0034 (8)0.0062 (8)0.0004 (8)
C30.0313 (10)0.0211 (9)0.0213 (9)−0.0013 (8)0.0052 (8)−0.0030 (7)
C40.0357 (12)0.0312 (11)0.0246 (10)0.0010 (9)0.0033 (8)0.0006 (8)
C50.0395 (12)0.0267 (11)0.0328 (11)−0.0030 (9)0.0138 (9)−0.0024 (9)
C60.0486 (15)0.0300 (13)0.0444 (14)0.0068 (11)0.0120 (11)0.0056 (10)
C70.0707 (19)0.0222 (12)0.0532 (16)−0.0010 (11)0.0243 (14)0.0028 (11)
C80.0578 (16)0.0326 (13)0.0508 (15)−0.0153 (12)0.0221 (13)−0.0107 (11)
C90.0431 (13)0.0353 (12)0.0390 (13)−0.0124 (10)0.0156 (10)−0.0085 (10)
C100.0344 (11)0.0274 (11)0.0319 (11)−0.0047 (9)0.0125 (9)−0.0061 (8)
C110.0430 (16)0.0574 (19)0.0562 (18)−0.0256 (14)0.0031 (13)−0.0075 (14)
C120.0273 (10)0.0216 (9)0.0202 (9)0.0031 (8)0.0040 (7)−0.0003 (7)
N130.0298 (9)0.0250 (9)0.0205 (8)−0.0011 (7)0.0013 (7)−0.0003 (6)
N140.0307 (9)0.0277 (9)0.0157 (7)−0.0041 (7)0.0021 (6)−0.0008 (6)
C210.0226 (9)0.0272 (10)0.0222 (9)0.0005 (8)0.0038 (7)−0.0001 (8)
C220.0330 (11)0.0388 (12)0.0213 (9)−0.0025 (9)0.0016 (8)−0.0040 (9)
C230.0348 (12)0.0401 (13)0.0343 (12)−0.0098 (10)0.0009 (9)−0.0126 (10)
C240.0353 (12)0.0366 (13)0.0382 (12)−0.0129 (10)0.0086 (9)−0.0012 (10)
C250.0339 (11)0.0357 (12)0.0294 (11)−0.0067 (9)0.0086 (9)0.0023 (9)
C260.0254 (10)0.0288 (11)0.0215 (9)−0.0002 (8)0.0037 (7)−0.0035 (8)
Cl1B0.0340 (3)0.0259 (2)0.0441 (3)0.0020 (2)0.0123 (2)−0.0069 (2)
N1B0.0301 (9)0.0269 (9)0.0284 (9)0.0002 (7)0.0026 (7)0.0008 (7)
C2B0.0304 (10)0.0214 (10)0.0242 (9)0.0058 (8)0.0039 (8)−0.0009 (7)
C3B0.0300 (10)0.0236 (10)0.0196 (9)0.0002 (8)0.0040 (7)0.0019 (7)
C4B0.0347 (12)0.0309 (11)0.0256 (10)0.0028 (9)0.0099 (8)0.0001 (8)
C5B0.0370 (11)0.0237 (10)0.0260 (10)0.0014 (9)0.0013 (8)0.0003 (8)
C6B0.0456 (14)0.0288 (12)0.0383 (13)0.0069 (10)0.0042 (10)−0.0060 (9)
C7B0.0547 (15)0.0223 (11)0.0416 (13)0.0069 (10)−0.0028 (11)−0.0064 (10)
C8B0.0453 (14)0.0265 (11)0.0429 (13)−0.0060 (10)−0.0049 (11)0.0018 (10)
C9B0.0358 (12)0.0280 (11)0.0358 (12)−0.0040 (9)−0.0035 (9)0.0028 (9)
C10B0.0308 (11)0.0238 (10)0.0279 (10)0.0012 (8)−0.0020 (8)0.0009 (8)
C11B0.0461 (16)0.0393 (15)0.0580 (18)−0.0152 (12)0.0130 (13)−0.0037 (12)
C12B0.0283 (10)0.0241 (10)0.0191 (9)0.0026 (8)0.0041 (7)0.0003 (7)
N13B0.0277 (9)0.0272 (9)0.0214 (8)0.0012 (7)0.0065 (7)−0.0007 (6)
N14B0.0341 (9)0.0297 (9)0.0189 (8)−0.0020 (8)0.0087 (7)0.0006 (7)
C21B0.0237 (9)0.0289 (10)0.0204 (9)0.0035 (8)0.0040 (7)0.0010 (8)
C22B0.0307 (11)0.0419 (13)0.0242 (10)−0.0012 (9)0.0087 (8)0.0054 (9)
C23B0.0347 (12)0.0416 (13)0.0344 (12)−0.0092 (10)0.0095 (9)0.0099 (10)
C24B0.0369 (12)0.0366 (13)0.0356 (12)−0.0118 (10)0.0024 (9)−0.0035 (10)
C25B0.0360 (12)0.0370 (12)0.0253 (10)−0.0065 (10)0.0013 (9)−0.0033 (9)
C26B0.0258 (10)0.0277 (10)0.0202 (9)0.0018 (8)0.0044 (7)0.0041 (8)

Geometric parameters (Å, °)

Cl1—C21.740 (2)Cl1B—C2B1.745 (2)
N1—C21.290 (3)N1B—C2B1.291 (3)
N1—C101.365 (3)N1B—C10B1.365 (3)
C2—C31.426 (3)C2B—C3B1.417 (3)
C3—C41.373 (3)C3B—C4B1.371 (3)
C3—C121.465 (3)C3B—C12B1.472 (3)
C4—C51.400 (3)C4B—C5B1.400 (3)
C4—H40.9500C4B—H4B0.9500
C5—C101.411 (3)C5B—C10B1.418 (3)
C5—C61.413 (3)C5B—C6B1.421 (3)
C6—C71.366 (4)C6B—C7B1.355 (4)
C6—H60.9500C6B—H6B0.9500
C7—C81.394 (4)C7B—C8B1.409 (4)
C7—H70.9500C7B—H7B0.9500
C8—C91.367 (4)C8B—C9B1.363 (3)
C8—H80.9500C8B—H8B0.9500
C9—C101.426 (3)C9B—C10B1.418 (3)
C9—C111.493 (4)C9B—C11B1.493 (4)
C11—H11A0.9800C11B—H11D0.9800
C11—H11B0.9800C11B—H11E0.9800
C11—H11C0.9800C11B—H11F0.9800
C12—N131.317 (3)C12B—N13B1.316 (3)
C12—N141.355 (3)C12B—N14B1.357 (3)
N13—C211.390 (3)N13B—C21B1.382 (3)
N14—C261.377 (3)N14B—C26B1.379 (3)
N14—H140.8800N14B—H14B0.8800
C21—C261.394 (3)C21B—C26B1.399 (3)
C21—C221.397 (3)C21B—C22B1.400 (3)
C22—C231.373 (3)C22B—C23B1.373 (3)
C22—H220.9500C22B—H22B0.9500
C23—C241.395 (3)C23B—C24B1.398 (3)
C23—H230.9500C23B—H23B0.9500
C24—C251.387 (3)C24B—C25B1.378 (3)
C24—H240.9500C24B—H24B0.9500
C25—C261.385 (3)C25B—C26B1.385 (3)
C25—H250.9500C25B—H25B0.9500
C2—N1—C10118.41 (19)C2B—N1B—C10B118.30 (19)
N1—C2—C3125.5 (2)N1B—C2B—C3B125.97 (19)
N1—C2—Cl1114.95 (16)N1B—C2B—Cl1B114.57 (16)
C3—C2—Cl1119.54 (16)C3B—C2B—Cl1B119.44 (16)
C4—C3—C2115.61 (19)C4B—C3B—C2B115.62 (19)
C4—C3—C12120.56 (19)C4B—C3B—C12B119.88 (19)
C2—C3—C12123.73 (18)C2B—C3B—C12B124.42 (19)
C3—C4—C5121.3 (2)C3B—C4B—C5B121.3 (2)
C3—C4—H4119.3C3B—C4B—H4B119.4
C5—C4—H4119.3C5B—C4B—H4B119.4
C4—C5—C10117.6 (2)C4B—C5B—C10B117.60 (19)
C4—C5—C6123.1 (2)C4B—C5B—C6B123.4 (2)
C10—C5—C6119.4 (2)C10B—C5B—C6B119.0 (2)
C7—C6—C5119.3 (3)C7B—C6B—C5B119.6 (2)
C7—C6—H6120.4C7B—C6B—H6B120.2
C5—C6—H6120.4C5B—C6B—H6B120.2
C6—C7—C8120.6 (2)C6B—C7B—C8B120.4 (2)
C6—C7—H7119.7C6B—C7B—H7B119.8
C8—C7—H7119.7C8B—C7B—H7B119.8
C9—C8—C7123.0 (2)C9B—C8B—C7B122.8 (2)
C9—C8—H8118.5C9B—C8B—H8B118.6
C7—C8—H8118.5C7B—C8B—H8B118.6
C8—C9—C10116.9 (2)C8B—C9B—C10B117.4 (2)
C8—C9—C11122.6 (2)C8B—C9B—C11B122.3 (2)
C10—C9—C11120.5 (2)C10B—C9B—C11B120.3 (2)
N1—C10—C5121.6 (2)N1B—C10B—C5B121.2 (2)
N1—C10—C9117.6 (2)N1B—C10B—C9B118.0 (2)
C5—C10—C9120.8 (2)C5B—C10B—C9B120.8 (2)
C9—C11—H11A109.5C9B—C11B—H11D109.5
C9—C11—H11B109.5C9B—C11B—H11E109.5
H11A—C11—H11B109.5H11D—C11B—H11E109.5
C9—C11—H11C109.5C9B—C11B—H11F109.5
H11A—C11—H11C109.5H11D—C11B—H11F109.5
H11B—C11—H11C109.5H11E—C11B—H11F109.5
N13—C12—N14113.42 (18)N13B—C12B—N14B113.23 (19)
N13—C12—C3123.21 (19)N13B—C12B—C3B123.41 (19)
N14—C12—C3123.37 (18)N14B—C12B—C3B123.36 (18)
C12—N13—C21104.42 (17)C12B—N13B—C21B104.81 (17)
C12—N14—C26106.86 (17)C12B—N14B—C26B106.83 (17)
C12—N14—H14126.6C12B—N14B—H14B126.6
C26—N14—H14126.6C26B—N14B—H14B126.6
N13—C21—C26109.92 (17)N13B—C21B—C26B109.97 (18)
N13—C21—C22130.18 (19)N13B—C21B—C22B130.41 (19)
C26—C21—C22119.89 (19)C26B—C21B—C22B119.6 (2)
C23—C22—C21117.8 (2)C23B—C22B—C21B117.7 (2)
C23—C22—H22121.1C23B—C22B—H22B121.2
C21—C22—H22121.1C21B—C22B—H22B121.2
C22—C23—C24121.8 (2)C22B—C23B—C24B121.9 (2)
C22—C23—H23119.1C22B—C23B—H23B119.0
C24—C23—H23119.1C24B—C23B—H23B119.0
C25—C24—C23121.3 (2)C25B—C24B—C23B121.2 (2)
C25—C24—H24119.4C25B—C24B—H24B119.4
C23—C24—H24119.4C23B—C24B—H24B119.4
C26—C25—C24116.6 (2)C24B—C25B—C26B116.9 (2)
C26—C25—H25121.7C24B—C25B—H25B121.6
C24—C25—H25121.7C26B—C25B—H25B121.6
N14—C26—C25131.94 (19)N14B—C26B—C25B132.18 (19)
N14—C26—C21105.38 (18)N14B—C26B—C21B105.15 (17)
C25—C26—C21122.66 (19)C25B—C26B—C21B122.65 (19)
C10—N1—C2—C3−0.2 (3)C10B—N1B—C2B—C3B−0.9 (3)
C10—N1—C2—Cl1−178.62 (15)C10B—N1B—C2B—Cl1B−179.39 (15)
N1—C2—C3—C4−0.7 (3)N1B—C2B—C3B—C4B−0.4 (3)
Cl1—C2—C3—C4177.67 (16)Cl1B—C2B—C3B—C4B178.08 (15)
N1—C2—C3—C12−177.0 (2)N1B—C2B—C3B—C12B−177.3 (2)
Cl1—C2—C3—C121.4 (3)Cl1B—C2B—C3B—C12B1.2 (3)
C2—C3—C4—C51.5 (3)C2B—C3B—C4B—C5B1.2 (3)
C12—C3—C4—C5177.9 (2)C12B—C3B—C4B—C5B178.29 (19)
C3—C4—C5—C10−1.4 (3)C3B—C4B—C5B—C10B−0.8 (3)
C3—C4—C5—C6179.0 (2)C3B—C4B—C5B—C6B178.2 (2)
C4—C5—C6—C7−179.8 (2)C4B—C5B—C6B—C7B−178.5 (2)
C10—C5—C6—C70.6 (4)C10B—C5B—C6B—C7B0.5 (3)
C5—C6—C7—C8−1.2 (4)C5B—C6B—C7B—C8B−0.9 (4)
C6—C7—C8—C91.4 (4)C6B—C7B—C8B—C9B0.9 (4)
C7—C8—C9—C10−1.0 (4)C7B—C8B—C9B—C10B−0.3 (4)
C7—C8—C9—C11178.7 (3)C7B—C8B—C9B—C11B179.9 (2)
C2—N1—C10—C50.3 (3)C2B—N1B—C10B—C5B1.3 (3)
C2—N1—C10—C9−179.4 (2)C2B—N1B—C10B—C9B−178.36 (19)
C4—C5—C10—N10.5 (3)C4B—C5B—C10B—N1B−0.5 (3)
C6—C5—C10—N1−179.9 (2)C6B—C5B—C10B—N1B−179.5 (2)
C4—C5—C10—C9−179.8 (2)C4B—C5B—C10B—C9B179.16 (19)
C6—C5—C10—C9−0.1 (3)C6B—C5B—C10B—C9B0.1 (3)
C8—C9—C10—N1−179.9 (2)C8B—C9B—C10B—N1B179.4 (2)
C11—C9—C10—N10.4 (3)C11B—C9B—C10B—N1B−0.7 (3)
C8—C9—C10—C50.3 (3)C8B—C9B—C10B—C5B−0.2 (3)
C11—C9—C10—C5−179.4 (2)C11B—C9B—C10B—C5B179.7 (2)
C4—C3—C12—N13−43.2 (3)C4B—C3B—C12B—N13B−42.0 (3)
C2—C3—C12—N13132.8 (2)C2B—C3B—C12B—N13B134.8 (2)
C4—C3—C12—N14137.2 (2)C4B—C3B—C12B—N14B137.7 (2)
C2—C3—C12—N14−46.7 (3)C2B—C3B—C12B—N14B−45.5 (3)
N14—C12—N13—C210.4 (2)C3B—C12B—N13B—C21B−179.77 (19)
C3—C12—N13—C21−179.16 (19)C3B—C12B—N14B—C26B179.69 (19)
N14—C12—N13—H14−0.3C12B—N13B—C21B—C26B−0.3 (2)
C3—C12—N13—H14−179.9H14B—N13B—C21B—C26B0.2
N13—C12—N14—C26−0.5 (2)C12B—N13B—C21B—C22B179.2 (2)
C3—C12—N14—C26179.07 (19)H14B—N13B—C21B—C22B179.7
C12—N13—C21—C26−0.2 (2)N13B—C21B—C22B—C23B−180.0 (2)
C12—N13—C21—C22178.9 (2)C26B—C21B—C22B—C23B−0.5 (3)
N13—C21—C22—C23−179.6 (2)C21B—C22B—C23B—C24B1.0 (3)
C26—C21—C22—C23−0.6 (3)C22B—C23B—C24B—C25B−0.4 (4)
C21—C22—C23—C241.3 (4)C23B—C24B—C25B—C26B−0.6 (4)
C22—C23—C24—C25−0.6 (4)C12B—N14B—C26B—C25B−178.7 (2)
C23—C24—C25—C26−0.8 (4)C12B—N14B—C26B—C21B0.4 (2)
C12—N14—C26—C25−178.0 (2)C24B—C25B—C26B—N14B180.0 (2)
C12—N14—C26—C210.4 (2)C24B—C25B—C26B—C21B1.0 (3)
C24—C25—C26—N14179.5 (2)N13B—C21B—C26B—N14B−0.1 (2)
C24—C25—C26—C211.4 (3)C22B—C21B—C26B—N14B−179.66 (19)
C22—C21—C26—N14−179.28 (19)N13B—C21B—C26B—C25B179.1 (2)
N13—C21—C26—C25178.4 (2)C22B—C21B—C26B—C25B−0.5 (3)
C22—C21—C26—C25−0.7 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N14—H14···N13i0.882.05 (1)2.851 (2)150
N14B—H14B···N13Bii0.882.02 (1)2.826 (2)151

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2183).

References

  • Bruker (2001). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Kim, H. N., Lee, H. K. & Lee, S. W. (2005). Bull. Korean Chem. Soc. 892–898.
  • Rominger, F., Malathi, M., Mohan, P. S., Ramamurthi Dondeti, T. & Hashmi, A. S. K. (2009). Acta Cryst. E65, o401.
  • Sheldrick, G. M. (2008a). Acta Cryst. A64, 112–122. [PubMed]
  • Sheldrick, G. M. (2008b). SADABS University of Göttingen, Germany.

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