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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o1987.
Published online 2008 September 24. doi:  10.1107/S160053680803002X
PMCID: PMC2959275

2-(3-Nitro­phen­yl)-4,5-diphenyl-1H-imidazol-3-ium chloride

Abstract

The title compound, C21H16N3O2 +·Cl, contains two organic cations with similar conformation and two chloride ions in the asymmetric unit. The imidazole and benzene rings are twisted with respect to each other [dihedral angles of 24.05 (16), 24.31 (16) and 50.38 (13) in one cation and 27.70 (15), 25.07 (16) and 45.86 (14)° in the other]. The crystal packing is stabilized by N—H(...)Cl hydrogen bonds, forming an infinite one-dimensional chain parallel to the c axis.

Related literature

For uses of imidazole derivatives, see: Dai & Fu (2008 [triangle]); Fu et al. (2008 [triangle]); Huang et al. (2008 [triangle]).

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Object name is e-64-o1987-scheme1.jpg

Experimental

Crystal data

  • C21H16N3O2 +·Cl
  • M r = 377.82
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1987-efi1.jpg
  • a = 9.7265 (19) Å
  • b = 12.364 (3) Å
  • c = 15.511 (3) Å
  • α = 91.97 (3)°
  • β = 90.15 (3)°
  • γ = 95.84 (3)°
  • V = 1854.5 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 298 (2) K
  • 0.24 × 0.20 × 0.18 mm

Data collection

  • Rigaku Mercury2 diffractometer
  • Absorption correction: multi-scan (CrystalClear, Rigaku, 2005 [triangle]) T min = 0.939, T max = 0.957
  • 18693 measured reflections
  • 8132 independent reflections
  • 5351 reflections with I > 2σ(I)
  • R int = 0.043

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.153
  • S = 1.07
  • 8132 reflections
  • 487 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; 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]) and SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803002X/dn2374sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803002X/dn2374Isup2.hkl

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

Acknowledgments

This work was supported by a start-up grant from Southeast University to Professor Ren-Gen Xiong.

supplementary crystallographic information

Comment

Imidazole derivatives have found wide range of applications in coordination chemistry because of their multiple coordination modes as ligands to metal ions and for the construction of novel metal-organic frameworks (Huang, et al. 2008; Fu, et al. 2008; Dai & Fu 2008). We report here the crystal structure of the title compound, di-2-(3'-nitrophenyl)-4,5-diphenyl-1H-imidazole-3-ium dichloride.

The title compound contains two organic cation with similar conformation and two Cl- ions in the asymmetric unit (Fig. 1). In both molecules the N atom of the imidazole is protonated. The imidazole and the benzene rings are twisted from each other by a dihedral angle of 24.05 (0.16) °, 24.31 (0.16) ° and 50.38 (0.13) ° (27.70 (0.15) °, 25.07 (0.16) ° and 45.86 (0.14) °) . The crystal packing is stabilized by N—H···Cl hydrogen bonds to form an infinite one-dimensional chain parallel to the c axis. (Table 1, Fig. 2).

Experimental

Under nitrogen protection, benzil (20 mmol), 3-nitrobenzaldehyde (20 mmol) and amine acetate (50 mmol) were added in a flask. The mixture was stirred at 110 °C for 20 h in the solution of HAC (60 ml). The resulting solution was poured into ice water (200 ml), white solid was obtained after adding NaOH (6 mol/L) till PH=7, then filtered and washed with distilled water. The crude product was recrystallized with the solution of ethanol (150 ml) and hydrochloric acid (5 ml) to yield colorless block-like crystals, suitable for X-ray analysis.

Refinement

All H atoms attached to C and N atoms were fixed geometrically and treated as riding with C–H = 0.93 Å (aromatic) and N–H = 0.86 Å with Uiso(H) =1.2Ueq(C or N).

Figures

Fig. 1.
A view of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small sphere of arbitrary radii. Hydrogen bonds are shown as dashed line.
Fig. 2.
The crystal packing of the title compound viewed along the a axis showing the one-dimensionnal hydrogen bonding chain. Hydrogen atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

Crystal data

C21H16N3O2+·ClZ = 4
Mr = 377.82F(000) = 784
Triclinic, P1Dx = 1.353 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.7265 (19) ÅCell parameters from 3688 reflections
b = 12.364 (3) Åθ = 2.5–27.1°
c = 15.511 (3) ŵ = 0.23 mm1
α = 91.97 (3)°T = 298 K
β = 90.15 (3)°Block, colorless
γ = 95.84 (3)°0.24 × 0.20 × 0.18 mm
V = 1854.5 (7) Å3

Data collection

Rigaku Mercury2 diffractometer8132 independent reflections
Radiation source: fine-focus sealed tube5351 reflections with I > 2σ(I)
graphiteRint = 0.043
Detector resolution: 13.6612 pixels mm-1θmax = 27.2°, θmin = 2.5°
ω scansh = −12→12
Absorption correction: multi-scan (CrystalClear, Rigaku, 2005)k = −15→15
Tmin = 0.939, Tmax = 0.957l = −19→19
18693 measured reflections

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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0593P)2 + 0.2499P] where P = (Fo2 + 2Fc2)/3
8132 reflections(Δ/σ)max = 0.009
487 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = −0.27 e Å3

Special details

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 > 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
Cl10.79840 (9)0.52921 (6)0.29960 (4)0.0600 (2)
N10.9375 (3)0.8492 (2)−0.07795 (17)0.0613 (7)
N20.6852 (2)0.45441 (16)−0.01555 (12)0.0391 (5)
H20.67650.4807−0.06560.047*
N30.7522 (2)0.43586 (16)0.11489 (12)0.0403 (5)
H30.79470.44800.16350.048*
O10.8327 (3)0.8432 (2)−0.12130 (19)0.1011 (10)
O21.0299 (3)0.9231 (2)−0.08381 (19)0.0942 (9)
C10.4870 (3)0.1792 (2)−0.02959 (18)0.0551 (7)
H10.52980.14840.01590.066*
C20.3941 (4)0.1151 (3)−0.0821 (2)0.0669 (9)
H2A0.37440.0417−0.07110.080*
C30.3307 (3)0.1583 (3)−0.1503 (2)0.0639 (8)
H3A0.26760.1149−0.18490.077*
C40.3613 (3)0.2660 (3)−0.16665 (18)0.0561 (7)
H40.31990.2952−0.21340.067*
C50.4534 (3)0.3323 (2)−0.11451 (16)0.0454 (6)
H50.47280.4055−0.12650.055*
C60.5168 (3)0.2898 (2)−0.04434 (15)0.0408 (6)
C70.6123 (2)0.3593 (2)0.01275 (15)0.0391 (6)
C80.6553 (3)0.3488 (2)0.09655 (15)0.0387 (5)
C90.6232 (3)0.2638 (2)0.15934 (15)0.0401 (6)
C100.7300 (3)0.2159 (2)0.19771 (17)0.0506 (7)
H100.82130.24180.18710.061*
C110.7012 (4)0.1304 (3)0.25142 (19)0.0624 (8)
H110.77320.09850.27680.075*
C120.5673 (4)0.0918 (2)0.26774 (19)0.0620 (8)
H120.54830.03300.30310.074*
C130.4609 (3)0.1404 (2)0.23154 (19)0.0594 (8)
H130.36990.11470.24320.071*
C140.4877 (3)0.2260 (2)0.17870 (17)0.0505 (7)
H140.41490.25910.15560.061*
C150.7710 (2)0.49879 (19)0.04687 (14)0.0368 (5)
C160.8719 (3)0.5943 (2)0.04194 (15)0.0381 (5)
C170.8556 (3)0.6750 (2)−0.01615 (15)0.0413 (6)
H170.77950.6703−0.05300.050*
C180.9557 (3)0.7625 (2)−0.01757 (16)0.0444 (6)
C191.0704 (3)0.7728 (2)0.03556 (19)0.0531 (7)
H191.13620.83260.03250.064*
C201.0856 (3)0.6926 (2)0.09320 (18)0.0515 (7)
H201.16210.69820.12980.062*
C210.9871 (3)0.6035 (2)0.09695 (16)0.0446 (6)
H210.99770.54960.13620.054*
Cl20.71004 (9)0.52695 (6)0.79879 (4)0.0598 (2)
N40.6666 (3)0.8561 (2)0.43176 (17)0.0660 (7)
N50.7989 (2)0.45279 (15)0.48411 (12)0.0364 (5)
H5A0.81390.47930.43410.044*
N60.7275 (2)0.43327 (16)0.61432 (12)0.0392 (5)
H60.68800.44490.66280.047*
O30.7518 (3)0.8431 (2)0.37747 (17)0.0901 (8)
O40.6168 (4)0.9416 (2)0.4429 (2)0.1358 (14)
C220.9164 (3)0.1767 (2)0.46440 (17)0.0496 (7)
H220.86180.14490.50760.059*
C230.9902 (3)0.1127 (2)0.41130 (19)0.0600 (8)
H230.98610.03820.41940.072*
C241.0702 (3)0.1585 (2)0.3462 (2)0.0590 (8)
H241.12120.11530.31110.071*
C251.0744 (3)0.2681 (2)0.33328 (18)0.0547 (7)
H251.12640.29860.28840.066*
C261.0017 (3)0.3328 (2)0.38663 (16)0.0436 (6)
H261.00540.40700.37750.052*
C270.9225 (2)0.2886 (2)0.45424 (15)0.0379 (5)
C280.8466 (2)0.35808 (19)0.51171 (14)0.0364 (5)
C290.8018 (2)0.34605 (19)0.59540 (15)0.0369 (5)
C300.8123 (3)0.26139 (19)0.65856 (15)0.0383 (5)
C310.6949 (3)0.2205 (2)0.70209 (16)0.0466 (6)
H310.61150.24910.69280.056*
C320.7009 (3)0.1376 (2)0.75902 (18)0.0568 (8)
H320.62180.11120.78830.068*
C330.8234 (4)0.0940 (2)0.77268 (18)0.0594 (8)
H330.82680.03690.80990.071*
C340.9410 (3)0.1354 (2)0.73084 (18)0.0571 (7)
H341.02410.10640.74040.069*
C350.9371 (3)0.2198 (2)0.67470 (17)0.0482 (6)
H351.01750.24840.64790.058*
C360.7259 (2)0.49708 (19)0.54660 (14)0.0363 (5)
C370.6520 (2)0.59366 (19)0.54290 (14)0.0366 (5)
C380.6928 (3)0.6761 (2)0.48667 (15)0.0407 (6)
H380.76680.67060.44950.049*
C390.6200 (3)0.7663 (2)0.48787 (17)0.0459 (6)
C400.5077 (3)0.7769 (2)0.54107 (18)0.0517 (7)
H400.46030.83850.53990.062*
C410.4678 (3)0.6940 (2)0.59584 (17)0.0496 (7)
H410.39240.69930.63200.060*
C420.5394 (3)0.6034 (2)0.59706 (16)0.0438 (6)
H420.51220.54810.63440.053*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0979 (6)0.0547 (4)0.0285 (3)0.0122 (4)−0.0013 (3)0.0057 (3)
N10.0720 (17)0.0502 (15)0.0619 (16)0.0012 (13)0.0075 (14)0.0166 (13)
N20.0499 (12)0.0419 (12)0.0257 (9)0.0048 (9)0.0000 (9)0.0048 (9)
N30.0497 (12)0.0445 (12)0.0266 (10)0.0028 (10)−0.0027 (9)0.0039 (9)
O10.0982 (19)0.090 (2)0.113 (2)−0.0149 (15)−0.0373 (17)0.0584 (18)
O20.0948 (18)0.0660 (16)0.119 (2)−0.0184 (14)−0.0024 (16)0.0381 (16)
C10.075 (2)0.0441 (16)0.0457 (15)0.0051 (14)−0.0094 (14)0.0028 (13)
C20.090 (2)0.0437 (17)0.065 (2)−0.0026 (16)−0.0108 (18)−0.0046 (15)
C30.0647 (19)0.061 (2)0.064 (2)0.0034 (16)−0.0181 (16)−0.0159 (16)
C40.0605 (18)0.066 (2)0.0437 (15)0.0183 (15)−0.0123 (13)−0.0069 (14)
C50.0487 (15)0.0482 (15)0.0408 (14)0.0120 (12)−0.0002 (12)0.0018 (12)
C60.0451 (14)0.0449 (14)0.0328 (12)0.0078 (11)0.0000 (11)−0.0025 (11)
C70.0450 (14)0.0411 (14)0.0321 (12)0.0082 (11)0.0004 (10)0.0038 (11)
C80.0459 (14)0.0388 (13)0.0315 (12)0.0031 (11)−0.0017 (10)0.0046 (10)
C90.0527 (15)0.0376 (13)0.0303 (12)0.0049 (11)−0.0011 (11)0.0028 (10)
C100.0568 (17)0.0524 (16)0.0440 (15)0.0107 (13)−0.0031 (13)0.0079 (13)
C110.090 (2)0.0538 (18)0.0466 (16)0.0225 (17)−0.0152 (16)0.0046 (14)
C120.102 (3)0.0368 (15)0.0455 (16)−0.0027 (16)−0.0046 (17)0.0093 (13)
C130.072 (2)0.0488 (17)0.0537 (17)−0.0120 (15)0.0016 (15)0.0090 (14)
C140.0564 (17)0.0485 (16)0.0466 (15)0.0026 (13)−0.0036 (13)0.0096 (13)
C150.0450 (14)0.0369 (13)0.0293 (11)0.0069 (10)0.0005 (10)0.0022 (10)
C160.0450 (14)0.0386 (13)0.0307 (12)0.0053 (11)0.0051 (10)−0.0016 (10)
C170.0450 (14)0.0453 (15)0.0339 (12)0.0053 (11)0.0011 (11)0.0032 (11)
C180.0542 (15)0.0396 (14)0.0396 (14)0.0051 (12)0.0043 (12)0.0039 (11)
C190.0544 (17)0.0483 (16)0.0545 (17)−0.0027 (13)0.0009 (13)−0.0054 (14)
C200.0520 (16)0.0506 (17)0.0509 (16)0.0033 (13)−0.0091 (13)−0.0058 (14)
C210.0524 (15)0.0469 (15)0.0358 (13)0.0117 (12)−0.0025 (11)−0.0021 (11)
Cl20.0970 (6)0.0540 (4)0.0279 (3)0.0041 (4)0.0030 (3)0.0048 (3)
N40.087 (2)0.0554 (16)0.0615 (16)0.0275 (14)0.0091 (15)0.0225 (13)
N50.0458 (11)0.0370 (11)0.0270 (10)0.0059 (9)0.0019 (8)0.0045 (8)
N60.0505 (12)0.0411 (11)0.0270 (10)0.0079 (9)0.0070 (9)0.0043 (9)
O30.119 (2)0.0720 (16)0.0863 (17)0.0297 (15)0.0429 (16)0.0379 (14)
O40.194 (3)0.0807 (19)0.151 (3)0.082 (2)0.083 (3)0.066 (2)
C220.0675 (18)0.0410 (15)0.0408 (14)0.0077 (13)0.0075 (13)0.0028 (12)
C230.083 (2)0.0437 (16)0.0544 (18)0.0159 (15)0.0040 (16)−0.0031 (14)
C240.0666 (19)0.0547 (18)0.0568 (18)0.0163 (15)0.0124 (15)−0.0132 (15)
C250.0547 (17)0.0615 (18)0.0471 (16)0.0035 (14)0.0128 (13)−0.0052 (14)
C260.0478 (15)0.0417 (14)0.0413 (14)0.0038 (11)0.0016 (11)0.0026 (11)
C270.0429 (13)0.0379 (13)0.0330 (12)0.0046 (10)−0.0013 (10)0.0003 (10)
C280.0443 (14)0.0357 (13)0.0296 (11)0.0041 (10)0.0003 (10)0.0053 (10)
C290.0444 (13)0.0365 (13)0.0302 (11)0.0060 (10)0.0010 (10)0.0039 (10)
C300.0503 (14)0.0334 (13)0.0313 (12)0.0047 (11)0.0016 (10)0.0040 (10)
C310.0538 (16)0.0450 (15)0.0407 (14)0.0016 (12)0.0041 (12)0.0050 (12)
C320.076 (2)0.0440 (16)0.0474 (16)−0.0111 (15)0.0093 (15)0.0098 (13)
C330.099 (2)0.0337 (14)0.0455 (16)0.0044 (15)−0.0031 (16)0.0085 (12)
C340.076 (2)0.0471 (17)0.0515 (17)0.0191 (15)−0.0077 (15)0.0054 (14)
C350.0551 (16)0.0481 (15)0.0427 (14)0.0093 (13)0.0043 (12)0.0061 (12)
C360.0444 (14)0.0376 (13)0.0272 (11)0.0049 (10)0.0003 (10)0.0026 (10)
C370.0429 (13)0.0379 (13)0.0294 (11)0.0071 (10)−0.0020 (10)−0.0011 (10)
C380.0452 (14)0.0441 (14)0.0340 (12)0.0103 (11)0.0020 (11)0.0039 (11)
C390.0572 (16)0.0428 (15)0.0396 (14)0.0126 (12)−0.0023 (12)0.0070 (12)
C400.0575 (17)0.0493 (16)0.0513 (16)0.0215 (13)−0.0036 (13)−0.0022 (13)
C410.0485 (15)0.0551 (17)0.0465 (15)0.0129 (13)0.0055 (12)−0.0042 (13)
C420.0486 (15)0.0445 (15)0.0373 (13)0.0012 (12)0.0014 (11)−0.0002 (11)

Geometric parameters (Å, °)

N1—O11.214 (3)N4—O31.201 (3)
N1—O21.221 (3)N4—O41.215 (3)
N1—C181.471 (3)N4—C391.470 (3)
N2—C151.342 (3)N5—C361.337 (3)
N2—C71.395 (3)N5—C281.384 (3)
N2—H20.8600N5—H5A0.8600
N3—C151.334 (3)N6—C361.336 (3)
N3—C81.378 (3)N6—C291.381 (3)
N3—H30.8600N6—H60.8600
C1—C21.384 (4)C22—C231.376 (4)
C1—C61.395 (4)C22—C271.393 (3)
C1—H10.9300C22—H220.9300
C2—C31.374 (4)C23—C241.378 (4)
C2—H2A0.9300C23—H230.9300
C3—C41.366 (4)C24—C251.373 (4)
C3—H3A0.9300C24—H240.9300
C4—C51.389 (4)C25—C261.378 (4)
C4—H40.9300C25—H250.9300
C5—C61.394 (3)C26—C271.396 (3)
C5—H50.9300C26—H260.9300
C6—C71.472 (3)C27—C281.468 (3)
C7—C81.379 (3)C28—C291.379 (3)
C8—C91.468 (3)C29—C301.469 (3)
C9—C101.390 (4)C30—C311.388 (3)
C9—C141.390 (4)C30—C351.392 (4)
C10—C111.376 (4)C31—C321.381 (4)
C10—H100.9300C31—H310.9300
C11—C121.368 (4)C32—C331.376 (4)
C11—H110.9300C32—H320.9300
C12—C131.376 (4)C33—C341.379 (4)
C12—H120.9300C33—H330.9300
C13—C141.366 (4)C34—C351.385 (4)
C13—H130.9300C34—H340.9300
C14—H140.9300C35—H350.9300
C15—C161.461 (3)C36—C371.458 (3)
C16—C171.388 (3)C37—C381.392 (3)
C16—C211.400 (3)C37—C421.395 (3)
C17—C181.381 (4)C38—C391.380 (3)
C17—H170.9300C38—H380.9300
C18—C191.378 (4)C39—C401.385 (4)
C19—C201.376 (4)C40—C411.379 (4)
C19—H190.9300C40—H400.9300
C20—C211.387 (4)C41—C421.379 (4)
C20—H200.9300C41—H410.9300
C21—H210.9300C42—H420.9300
O1—N1—O2122.6 (3)O3—N4—O4122.5 (3)
O1—N1—C18118.8 (2)O3—N4—C39119.7 (2)
O2—N1—C18118.6 (3)O4—N4—C39117.8 (3)
C15—N2—C7110.03 (19)C36—N5—C28110.09 (19)
C15—N2—H2125.0C36—N5—H5A125.0
C7—N2—H2125.0C28—N5—H5A125.0
C15—N3—C8110.7 (2)C36—N6—C29110.38 (19)
C15—N3—H3124.7C36—N6—H6124.8
C8—N3—H3124.7C29—N6—H6124.8
C2—C1—C6120.5 (3)C23—C22—C27120.9 (3)
C2—C1—H1119.8C23—C22—H22119.5
C6—C1—H1119.8C27—C22—H22119.5
C3—C2—C1120.9 (3)C22—C23—C24120.2 (3)
C3—C2—H2A119.6C22—C23—H23119.9
C1—C2—H2A119.6C24—C23—H23119.9
C4—C3—C2119.3 (3)C25—C24—C23119.9 (3)
C4—C3—H3A120.4C25—C24—H24120.0
C2—C3—H3A120.4C23—C24—H24120.0
C3—C4—C5121.0 (3)C24—C25—C26120.2 (3)
C3—C4—H4119.5C24—C25—H25119.9
C5—C4—H4119.5C26—C25—H25119.9
C4—C5—C6120.3 (3)C25—C26—C27120.9 (3)
C4—C5—H5119.8C25—C26—H26119.5
C6—C5—H5119.8C27—C26—H26119.5
C5—C6—C1118.1 (2)C22—C27—C26117.8 (2)
C5—C6—C7121.1 (2)C22—C27—C28121.4 (2)
C1—C6—C7120.8 (2)C26—C27—C28120.8 (2)
C8—C7—N2105.8 (2)C29—C28—N5106.3 (2)
C8—C7—C6132.3 (2)C29—C28—C27131.8 (2)
N2—C7—C6121.9 (2)N5—C28—C27121.8 (2)
N3—C8—C7106.5 (2)C28—C29—N6106.1 (2)
N3—C8—C9121.0 (2)C28—C29—C30133.4 (2)
C7—C8—C9132.4 (2)N6—C29—C30120.4 (2)
C10—C9—C14118.7 (2)C31—C30—C35119.1 (2)
C10—C9—C8119.6 (2)C31—C30—C29119.5 (2)
C14—C9—C8121.6 (2)C35—C30—C29121.4 (2)
C11—C10—C9120.2 (3)C32—C31—C30120.5 (3)
C11—C10—H10119.9C32—C31—H31119.7
C9—C10—H10119.9C30—C31—H31119.7
C12—C11—C10120.4 (3)C33—C32—C31120.3 (3)
C12—C11—H11119.8C33—C32—H32119.8
C10—C11—H11119.8C31—C32—H32119.8
C11—C12—C13119.7 (3)C32—C33—C34119.5 (3)
C11—C12—H12120.1C32—C33—H33120.2
C13—C12—H12120.1C34—C33—H33120.2
C14—C13—C12120.6 (3)C33—C34—C35120.8 (3)
C14—C13—H13119.7C33—C34—H34119.6
C12—C13—H13119.7C35—C34—H34119.6
C13—C14—C9120.3 (3)C34—C35—C30119.7 (3)
C13—C14—H14119.9C34—C35—H35120.2
C9—C14—H14119.9C30—C35—H35120.2
N3—C15—N2107.0 (2)N5—C36—N6107.1 (2)
N3—C15—C16125.3 (2)N5—C36—C37127.9 (2)
N2—C15—C16127.7 (2)N6—C36—C37125.0 (2)
C17—C16—C21119.9 (2)C38—C37—C42119.8 (2)
C17—C16—C15121.3 (2)C38—C37—C36121.0 (2)
C21—C16—C15118.8 (2)C42—C37—C36119.2 (2)
C18—C17—C16118.0 (2)C39—C38—C37117.9 (2)
C18—C17—H17121.0C39—C38—H38121.0
C16—C17—H17121.0C37—C38—H38121.0
C19—C18—C17123.0 (3)C38—C39—C40122.9 (2)
C19—C18—N1118.8 (2)C38—C39—N4118.3 (2)
C17—C18—N1118.2 (2)C40—C39—N4118.8 (2)
C20—C19—C18118.6 (3)C41—C40—C39118.5 (2)
C20—C19—H19120.7C41—C40—H40120.8
C18—C19—H19120.7C39—C40—H40120.8
C19—C20—C21120.2 (3)C42—C41—C40120.1 (3)
C19—C20—H20119.9C42—C41—H41120.0
C21—C20—H20119.9C40—C41—H41120.0
C20—C21—C16120.2 (3)C41—C42—C37120.8 (2)
C20—C21—H21119.9C41—C42—H42119.6
C16—C21—H21119.9C37—C42—H42119.6

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3···Cl10.862.303.066 (2)148.
N5—H5A···Cl10.862.203.045 (2)166.
N6—H6···Cl20.862.313.061 (2)146.
N2—H2···Cl2i0.862.213.048 (2)163.

Symmetry codes: (i) x, y, z−1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2374).

References

  • Dai, W. & Fu, D.-W. (2008). Acta Cryst. E64, o971. [PMC free article] [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Fu, D.-W. & Xiong, R.-G. (2008). Dalton Trans. pp. 3946–3948. [PubMed]
  • Huang, X.-F., Fu, D.-W. & Xiong, R.-G. (2008). Cryst. Growth Des.8, 1795–1797.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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