Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
Mol­ecules of 1,2-bis­(4-bromo­phenyl)-1H-benzimidazole, C19H12Br2N2, (I), and 2-(4-bromo­phenyl)-1-(4-nitro­phenyl)-1H-benzimidazole, C19H12BrN3O2, (II), are arranged in dimeric units through C—H...N and parallel-displaced π-stacking inter­actions favoured by the appropriate disposition of N- and C-bonded phenyl rings with respect to the mean benzimidazole plane. The mol­ecular packing of the dimers of (I) and (II) arises by the concurrence of a diverse set of weak inter­molecular C—X...D (X = H, NO2; D = O, π) inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229613033329/fg3315sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229613033329/fg3315Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229613033329/fg3315IIsup3.hkl
Contains datablock II

CCDC references: 975726; 975727

Computing details top

For both compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008). Software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), WinGX2003 (Farrugia, 2012) and publCIF (Westrip, 2010) for (I); SHELXL97 (Sheldrick, 2008), and WinGX2003 (Farrugia, 2012) and publCIF (Westrip, 2010) for (II).

(I) 1,2-Bis(4-bromophenyl)-1H-benzimidazole top
Crystal data top
C19H12Br2N2Z = 2
Mr = 428.13F(000) = 420
Triclinic, P1Dx = 1.713 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54184 Å
a = 7.6621 (5) ÅCell parameters from 600 reflections
b = 10.8241 (7) Åθ = 20–25°
c = 11.0422 (7) ŵ = 6.18 mm1
α = 105.078 (6)°T = 293 K
β = 106.456 (6)°Block, colourless
γ = 96.677 (5)°0.30 × 0.26 × 0.24 × 0.15 (radius) mm
V = 830.00 (9) Å3
Data collection top
Oxford Xcalibur Ruby Gemini
diffractometer
3743 independent reflections
Radiation source: fine-focus sealed tube2586 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
ω scansθmax = 88.7°, θmin = 6.8°
Absorption correction: for a sphere
(Dwiggins, 1975)
h = 99
Tmin = 0.278, Tmax = 0.360k = 1413
12778 measured reflectionsl = 1414
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0717P)2]
where P = (Fo2 + 2Fc2)/3
3743 reflections(Δ/σ)max = 0.001
208 parametersΔρmax = 0.95 e Å3
0 restraintsΔρmin = 0.61 e Å3
Special details top

Experimental. Interpolation using International Tables Vol. C (1992) p. 523, Table 6.3.3.3 for values of muR in the range 0–2.5, and International Tables Vol. II (1959) p. 302, Table 5.3.6B for muR in the range 2.6–10.0. The interpolation procedure of C. W. Dwiggins Jr [Acta Cryst. (1975) A31, 146–148] is used with some modification.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Br130.79691 (5)1.06330 (4)0.37402 (4)0.0578 (2)
Br190.27246 (8)0.31022 (5)0.53911 (5)0.0743 (2)
N10.0150 (4)0.7327 (3)0.1590 (3)0.0445 (10)
N30.2154 (4)0.5539 (3)0.0613 (3)0.0506 (11)
C20.0499 (5)0.6033 (3)0.1501 (3)0.0456 (12)
C40.4298 (6)0.6530 (5)0.0892 (4)0.0618 (14)
C50.4474 (6)0.7648 (5)0.1212 (4)0.0706 (18)
C60.3039 (6)0.8790 (5)0.0575 (5)0.0685 (17)
C70.1426 (6)0.8787 (4)0.0360 (4)0.0550 (12)
C80.1251 (5)0.7645 (4)0.0674 (3)0.0450 (11)
C90.2665 (5)0.6523 (4)0.0072 (3)0.0488 (12)
C100.2012 (5)0.8076 (3)0.2149 (3)0.0403 (11)
C110.2371 (5)0.9339 (3)0.2995 (3)0.0438 (11)
C120.4150 (5)1.0091 (3)0.3460 (3)0.0456 (11)
C130.5540 (5)0.9570 (3)0.3094 (3)0.0409 (11)
C140.5201 (5)0.8317 (3)0.2268 (4)0.0474 (12)
C150.3435 (5)0.7565 (3)0.1794 (4)0.0466 (11)
C160.0443 (5)0.5365 (3)0.2413 (4)0.0453 (12)
C170.1621 (6)0.6025 (4)0.3688 (4)0.0581 (16)
C180.2324 (6)0.5361 (4)0.4575 (4)0.0633 (17)
C190.1843 (6)0.4016 (4)0.4168 (4)0.0539 (14)
C200.0694 (7)0.3340 (4)0.2901 (4)0.0647 (16)
C210.0014 (6)0.4003 (4)0.2028 (4)0.0575 (14)
H40.524230.578700.130440.0744*
H50.554690.766790.185760.0848*
H60.319970.955050.079790.0821*
H70.048110.952900.076940.0658*
H110.142240.967810.324760.0524*
H120.440141.094460.401750.0547*
H140.615980.797740.203100.0570*
H150.319550.671340.123400.0557*
H170.194850.693290.395540.0695*
H180.310780.581670.543130.0760*
H200.039490.243190.263200.0775*
H210.080290.353940.117480.0693*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br130.0380 (3)0.0566 (3)0.0641 (3)0.0054 (2)0.0143 (2)0.0033 (2)
Br190.0863 (4)0.0669 (3)0.0877 (4)0.0334 (3)0.0341 (3)0.0398 (3)
N10.0392 (16)0.0431 (17)0.0486 (17)0.0007 (13)0.0152 (14)0.0127 (14)
N30.0422 (18)0.0495 (19)0.0511 (18)0.0052 (15)0.0152 (15)0.0072 (15)
C20.046 (2)0.041 (2)0.046 (2)0.0018 (16)0.0211 (18)0.0050 (16)
C40.044 (2)0.080 (3)0.049 (2)0.007 (2)0.008 (2)0.016 (2)
C50.049 (2)0.093 (4)0.068 (3)0.002 (2)0.004 (2)0.044 (3)
C60.061 (3)0.079 (3)0.070 (3)0.009 (2)0.014 (2)0.041 (2)
C70.049 (2)0.059 (2)0.058 (2)0.0007 (19)0.016 (2)0.026 (2)
C80.0385 (19)0.053 (2)0.0431 (19)0.0009 (16)0.0155 (16)0.0153 (17)
C90.043 (2)0.055 (2)0.045 (2)0.0026 (17)0.0177 (18)0.0117 (18)
C100.0401 (19)0.0387 (19)0.0401 (19)0.0013 (15)0.0139 (16)0.0110 (15)
C110.0391 (19)0.043 (2)0.048 (2)0.0106 (15)0.0166 (16)0.0082 (16)
C120.047 (2)0.0364 (19)0.045 (2)0.0057 (16)0.0123 (17)0.0027 (15)
C130.0343 (18)0.0405 (19)0.0401 (18)0.0007 (15)0.0080 (15)0.0078 (15)
C140.043 (2)0.045 (2)0.053 (2)0.0098 (16)0.0215 (18)0.0065 (17)
C150.049 (2)0.0353 (19)0.051 (2)0.0029 (16)0.0200 (18)0.0043 (16)
C160.045 (2)0.041 (2)0.050 (2)0.0036 (16)0.0225 (18)0.0089 (16)
C170.068 (3)0.037 (2)0.061 (3)0.0049 (19)0.016 (2)0.0096 (18)
C180.068 (3)0.053 (3)0.058 (3)0.009 (2)0.010 (2)0.012 (2)
C190.061 (2)0.046 (2)0.067 (3)0.0195 (19)0.031 (2)0.023 (2)
C200.085 (3)0.035 (2)0.076 (3)0.005 (2)0.036 (3)0.013 (2)
C210.069 (3)0.040 (2)0.056 (2)0.0013 (19)0.023 (2)0.0049 (18)
Geometric parameters (Å, º) top
Br13—C131.903 (4)C14—C151.374 (6)
Br19—C191.895 (4)C16—C171.384 (6)
N1—C21.399 (5)C16—C211.395 (6)
N1—C81.395 (5)C17—C181.387 (6)
N1—C101.430 (5)C18—C191.378 (6)
N3—C21.312 (5)C19—C201.374 (6)
N3—C91.393 (5)C20—C211.376 (6)
C2—C161.465 (5)C4—H40.9300
C4—C51.357 (8)C5—H50.9300
C4—C91.397 (6)C6—H60.9300
C5—C61.423 (7)C7—H70.9300
C6—C71.369 (7)C11—H110.9300
C7—C81.379 (6)C12—H120.9300
C8—C91.399 (6)C14—H140.9300
C10—C111.386 (5)C15—H150.9300
C10—C151.385 (6)C17—H170.9300
C11—C121.383 (5)C18—H180.9300
C12—C131.371 (5)C20—H200.9300
C13—C141.371 (5)C21—H210.9300
C2—N1—C8105.9 (3)C17—C18—C19119.0 (4)
C2—N1—C10128.8 (3)Br19—C19—C18119.3 (3)
C8—N1—C10122.7 (3)Br19—C19—C20120.0 (3)
C2—N3—C9106.2 (3)C18—C19—C20120.6 (4)
N1—C2—N3112.2 (3)C19—C20—C21120.2 (4)
N1—C2—C16123.8 (3)C16—C21—C20120.5 (4)
N3—C2—C16123.5 (3)C5—C4—H4121.00
C5—C4—C9118.4 (4)C9—C4—H4121.00
C4—C5—C6121.0 (4)C4—C5—H5120.00
C5—C6—C7121.1 (5)C6—C5—H5120.00
C6—C7—C8117.7 (4)C5—C6—H6119.00
N1—C8—C7132.2 (4)C7—C6—H6119.00
N1—C8—C9106.0 (4)C6—C7—H7121.00
C7—C8—C9121.8 (4)C8—C7—H7121.00
N3—C9—C4130.2 (4)C10—C11—H11120.00
N3—C9—C8109.6 (3)C12—C11—H11120.00
C4—C9—C8120.1 (4)C11—C12—H12120.00
N1—C10—C11119.7 (3)C13—C12—H12120.00
N1—C10—C15120.1 (3)C13—C14—H14120.00
C11—C10—C15120.1 (3)C15—C14—H14120.00
C10—C11—C12119.5 (4)C10—C15—H15120.00
C11—C12—C13119.6 (3)C14—C15—H15120.00
Br13—C13—C12118.6 (2)C16—C17—H17119.00
Br13—C13—C14120.1 (3)C18—C17—H17119.00
C12—C13—C14121.3 (4)C17—C18—H18121.00
C13—C14—C15119.6 (4)C19—C18—H18121.00
C10—C15—C14120.0 (3)C19—C20—H20120.00
C2—C16—C17122.9 (3)C21—C20—H20120.00
C2—C16—C21118.4 (3)C16—C21—H21120.00
C17—C16—C21118.4 (4)C20—C21—H21120.00
C16—C17—C18121.4 (4)
C8—N1—C2—N30.4 (4)C6—C7—C8—N1177.7 (4)
C10—N1—C2—N3161.6 (3)C7—C8—C9—C41.1 (6)
C8—N1—C2—C16172.0 (3)N1—C8—C9—N30.5 (4)
C10—N1—C2—C1626.0 (6)N1—C8—C9—C4179.1 (3)
C2—N1—C8—C90.5 (4)C7—C8—C9—N3177.5 (4)
C10—N1—C8—C9162.9 (3)N1—C10—C11—C12175.5 (3)
C8—N1—C10—C1167.2 (4)C15—C10—C11—C121.2 (5)
C2—N1—C10—C1549.8 (5)N1—C10—C15—C14175.9 (3)
C8—N1—C10—C15109.6 (4)C11—C10—C15—C140.8 (5)
C2—N1—C10—C11133.5 (4)C10—C11—C12—C131.0 (5)
C2—N1—C8—C7177.2 (4)C11—C12—C13—Br13179.6 (2)
C10—N1—C8—C719.5 (6)C11—C12—C13—C140.4 (5)
C2—N3—C9—C80.3 (4)Br13—C13—C14—C15179.1 (3)
C9—N3—C2—C16172.3 (3)C12—C13—C14—C150.1 (5)
C2—N3—C9—C4178.7 (4)C13—C14—C15—C100.2 (6)
C9—N3—C2—N10.0 (4)C2—C16—C17—C18172.6 (4)
N3—C2—C16—C2126.2 (6)C21—C16—C17—C180.7 (7)
N1—C2—C16—C21162.4 (4)C2—C16—C21—C20173.5 (4)
N3—C2—C16—C17147.1 (4)C17—C16—C21—C200.1 (7)
N1—C2—C16—C1724.3 (6)C16—C17—C18—C190.4 (7)
C9—C4—C5—C60.5 (7)C17—C18—C19—Br19177.8 (4)
C5—C4—C9—C80.6 (6)C17—C18—C19—C200.4 (7)
C5—C4—C9—N3177.6 (4)Br19—C19—C20—C21177.2 (4)
C4—C5—C6—C71.3 (7)C18—C19—C20—C211.0 (8)
C5—C6—C7—C80.8 (7)C19—C20—C21—C160.8 (8)
C6—C7—C8—C90.4 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···N3i0.932.603.525 (5)171
Symmetry code: (i) x, y+1, z.
(II) 2-(4-Bromophenyl)-1-(4-nitrophenyl)-1H-benzimidazole top
Crystal data top
C19H12BrN3O2Z = 2
Mr = 394.23F(000) = 396
Triclinic, P1Dx = 1.540 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54184 Å
a = 7.8689 (4) ÅCell parameters from 600 reflections
b = 10.0444 (4) Åθ = 20–25°
c = 11.8867 (5) ŵ = 3.44 mm1
α = 68.534 (4)°T = 293 K
β = 76.677 (4)°Block, pale yellow
γ = 86.869 (4)°0.33 × 0.28 × 0.26 × 0.15 (radius) mm
V = 850.35 (7) Å3
Data collection top
Oxford Xcalibur Ruby Gemini
diffractometer
3030 reflections with I > 2σ(I)
ω scansRint = 0.026
Absorption correction: for a sphere
(Dwiggins, 1975)
θmax = 78.7°, θmin = 4.1°
Tmin = 0.482, Tmax = 0.527h = 99
15531 measured reflectionsk = 1212
3560 independent reflectionsl = 1514
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.124 w = 1/[σ2(Fo2) + (0.0545P)2 + 0.2882P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
3560 reflectionsΔρmax = 0.66 e Å3
227 parametersΔρmin = 0.64 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0033 (4)
Special details top

Experimental. Interpolation using International Tables Vol. C (1992) p. 523, Table 6.3.3.3 for values of muR in the range 0–2.5, and International Tables Vol. II (1959) p. 302, Table 5.3.6B for muR in the range 2.6–10.0. The interpolation procedure of C. W. Dwiggins Jr [Acta Cryst. (1975) A31, 146–148] is used with some modification.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Br190.60320 (6)0.13648 (4)0.82836 (5)0.1183 (2)
O13A0.7074 (3)0.3829 (3)0.0574 (2)0.0966 (10)
O13B0.9350 (3)0.2692 (2)0.01132 (19)0.0861 (8)
N10.7690 (2)0.56674 (18)0.38271 (15)0.0494 (5)
N30.7743 (3)0.5887 (2)0.56310 (17)0.0541 (6)
N130.8165 (3)0.3464 (2)0.00549 (17)0.0657 (7)
C20.7574 (3)0.4986 (2)0.50915 (18)0.0478 (6)
C40.8273 (4)0.8556 (3)0.4756 (3)0.0723 (10)
C50.8505 (4)0.9725 (3)0.3676 (3)0.0810 (10)
C60.8461 (4)0.9605 (3)0.2556 (3)0.0789 (10)
C70.8192 (3)0.8298 (3)0.2468 (2)0.0655 (8)
C80.7955 (3)0.7120 (2)0.3568 (2)0.0529 (6)
C90.7992 (3)0.7219 (2)0.4700 (2)0.0552 (7)
C100.7804 (3)0.5068 (2)0.28960 (17)0.0465 (6)
C110.6561 (3)0.5410 (3)0.2189 (2)0.0617 (8)
C120.6677 (3)0.4881 (3)0.1259 (2)0.0641 (8)
C130.8037 (3)0.4013 (2)0.10580 (18)0.0523 (6)
C140.9286 (3)0.3662 (2)0.17517 (19)0.0514 (6)
C150.9178 (3)0.4205 (2)0.26803 (18)0.0479 (6)
C160.7222 (3)0.3448 (2)0.57881 (18)0.0483 (6)
C170.6422 (3)0.2541 (3)0.5397 (2)0.0565 (7)
C180.6075 (3)0.1116 (3)0.6135 (3)0.0676 (8)
C190.6509 (3)0.0601 (3)0.7270 (3)0.0692 (8)
C200.7277 (3)0.1465 (3)0.7696 (2)0.0687 (8)
C210.7630 (3)0.2876 (3)0.6953 (2)0.0584 (7)
H40.830050.864680.550240.0867*
H50.869821.062170.369230.0970*
H60.861711.042610.184370.0947*
H70.817060.821640.171710.0786*
H110.565020.599550.234220.0740*
H120.585230.510610.077420.0769*
H141.018750.306890.159920.0617*
H151.001650.399320.315310.0575*
H170.611950.289990.463160.0678*
H180.555380.051330.586700.0811*
H200.755000.109990.847120.0824*
H210.815510.346740.723030.0701*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br190.1101 (3)0.0678 (3)0.1331 (4)0.0110 (2)0.0188 (3)0.0108 (2)
O13A0.1064 (17)0.139 (2)0.0682 (12)0.0022 (14)0.0304 (12)0.0578 (13)
O13B0.1190 (17)0.0811 (13)0.0639 (10)0.0078 (12)0.0073 (11)0.0416 (10)
N10.0547 (10)0.0521 (9)0.0435 (8)0.0066 (7)0.0096 (7)0.0215 (7)
N30.0593 (10)0.0600 (10)0.0534 (9)0.0094 (8)0.0177 (8)0.0306 (8)
N130.0830 (14)0.0691 (12)0.0439 (9)0.0152 (10)0.0015 (9)0.0247 (9)
C20.0469 (10)0.0585 (11)0.0440 (9)0.0084 (8)0.0128 (8)0.0250 (9)
C40.0768 (17)0.0651 (15)0.0908 (18)0.0109 (12)0.0260 (14)0.0436 (14)
C50.0857 (19)0.0546 (14)0.106 (2)0.0044 (13)0.0191 (16)0.0349 (15)
C60.0808 (18)0.0531 (13)0.0867 (19)0.0058 (12)0.0068 (14)0.0146 (12)
C70.0690 (15)0.0605 (13)0.0589 (13)0.0097 (11)0.0073 (11)0.0178 (10)
C80.0502 (11)0.0536 (11)0.0562 (11)0.0086 (9)0.0093 (9)0.0241 (9)
C90.0543 (12)0.0570 (12)0.0620 (12)0.0096 (9)0.0157 (9)0.0300 (10)
C100.0478 (10)0.0529 (10)0.0390 (9)0.0029 (8)0.0067 (7)0.0191 (8)
C110.0539 (12)0.0828 (16)0.0563 (12)0.0192 (11)0.0175 (10)0.0339 (12)
C120.0585 (13)0.0902 (17)0.0528 (12)0.0071 (11)0.0219 (10)0.0316 (12)
C130.0610 (12)0.0576 (11)0.0377 (9)0.0082 (9)0.0052 (8)0.0188 (8)
C140.0571 (12)0.0483 (10)0.0467 (10)0.0026 (8)0.0046 (8)0.0193 (8)
C150.0497 (10)0.0504 (10)0.0448 (9)0.0039 (8)0.0128 (8)0.0178 (8)
C160.0465 (10)0.0559 (11)0.0435 (9)0.0069 (8)0.0069 (8)0.0220 (8)
C170.0533 (12)0.0645 (13)0.0523 (11)0.0018 (9)0.0097 (9)0.0228 (10)
C180.0619 (14)0.0636 (14)0.0746 (15)0.0065 (11)0.0065 (12)0.0264 (12)
C190.0589 (14)0.0568 (13)0.0715 (15)0.0013 (10)0.0035 (11)0.0066 (11)
C200.0667 (15)0.0747 (16)0.0546 (12)0.0087 (12)0.0160 (11)0.0115 (11)
C210.0588 (13)0.0673 (13)0.0506 (11)0.0084 (10)0.0140 (9)0.0231 (10)
Geometric parameters (Å, º) top
Br19—C191.903 (3)C13—C141.376 (3)
O13A—N131.221 (3)C14—C151.384 (3)
O13B—N131.208 (3)C16—C171.396 (4)
N1—C21.388 (3)C16—C211.398 (3)
N1—C81.394 (3)C17—C181.381 (4)
N1—C101.425 (3)C18—C191.374 (4)
N3—C21.314 (3)C19—C201.377 (4)
N3—C91.378 (3)C20—C211.371 (4)
N13—C131.468 (3)C4—H40.9300
C2—C161.468 (3)C5—H50.9300
C4—C51.368 (5)C6—H60.9300
C4—C91.401 (4)C7—H70.9300
C5—C61.388 (5)C11—H110.9300
C6—C71.386 (4)C12—H120.9300
C7—C81.387 (3)C14—H140.9300
C8—C91.392 (3)C15—H150.9300
C10—C111.383 (3)C17—H170.9300
C10—C151.385 (3)C18—H180.9300
C11—C121.375 (4)C20—H200.9300
C12—C131.377 (4)C21—H210.9300
C2—N1—C8106.13 (17)C17—C16—C21118.1 (2)
C2—N1—C10129.54 (18)C16—C17—C18120.7 (2)
C8—N1—C10123.67 (17)C17—C18—C19119.1 (3)
C2—N3—C9105.68 (18)Br19—C19—C18119.0 (2)
O13A—N13—O13B123.6 (2)Br19—C19—C20119.1 (2)
O13A—N13—C13117.9 (2)C18—C19—C20121.9 (3)
O13B—N13—C13118.5 (2)C19—C20—C21118.6 (2)
N1—C2—N3112.33 (19)C16—C21—C20121.6 (2)
N1—C2—C16125.22 (19)C5—C4—H4121.00
N3—C2—C16122.40 (18)C9—C4—H4121.00
C5—C4—C9117.8 (3)C4—C5—H5119.00
C4—C5—C6121.7 (3)C6—C5—H5119.00
C5—C6—C7122.0 (3)C5—C6—H6119.00
C6—C7—C8116.0 (2)C7—C6—H6119.00
N1—C8—C7131.8 (2)C6—C7—H7122.00
N1—C8—C9105.24 (18)C8—C7—H7122.00
C7—C8—C9122.9 (2)C10—C11—H11120.00
N3—C9—C4129.7 (2)C12—C11—H11120.00
N3—C9—C8110.62 (19)C11—C12—H12121.00
C4—C9—C8119.7 (2)C13—C12—H12121.00
N1—C10—C11118.7 (2)C13—C14—H14121.00
N1—C10—C15120.08 (19)C15—C14—H14121.00
C11—C10—C15121.1 (2)C10—C15—H15120.00
C10—C11—C12119.7 (2)C14—C15—H15120.00
C11—C12—C13118.8 (2)C16—C17—H17120.00
N13—C13—C12118.5 (2)C18—C17—H17120.00
N13—C13—C14119.2 (2)C17—C18—H18120.00
C12—C13—C14122.3 (2)C19—C18—H18120.00
C13—C14—C15118.9 (2)C19—C20—H20121.00
C10—C15—C14119.1 (2)C21—C20—H20121.00
C2—C16—C17124.5 (2)C16—C21—H21119.00
C2—C16—C21117.4 (2)C20—C21—H21119.00
C8—N1—C2—N30.0 (3)C5—C6—C7—C80.5 (4)
C8—N1—C2—C16177.3 (2)C6—C7—C8—N1178.7 (3)
C10—N1—C2—N3170.8 (2)C6—C7—C8—C90.4 (4)
C10—N1—C2—C1611.9 (4)N1—C8—C9—N30.6 (3)
C2—N1—C8—C7178.8 (3)N1—C8—C9—C4178.9 (2)
C2—N1—C8—C90.3 (2)C7—C8—C9—N3179.2 (2)
C10—N1—C8—C77.3 (4)C7—C8—C9—C40.2 (4)
C10—N1—C8—C9171.2 (2)N1—C10—C11—C12177.9 (2)
C2—N1—C10—C11123.1 (2)C15—C10—C11—C120.4 (4)
C2—N1—C10—C1559.4 (3)N1—C10—C15—C14178.47 (19)
C8—N1—C10—C1167.5 (3)C11—C10—C15—C141.0 (3)
C8—N1—C10—C15110.0 (2)C10—C11—C12—C130.2 (4)
C9—N3—C2—N10.4 (3)C11—C12—C13—N13179.3 (2)
C9—N3—C2—C16177.7 (2)C11—C12—C13—C140.3 (4)
C2—N3—C9—C4178.8 (3)N13—C13—C14—C15178.8 (2)
C2—N3—C9—C80.6 (3)C12—C13—C14—C150.3 (3)
O13A—N13—C13—C121.5 (3)C13—C14—C15—C100.9 (3)
O13A—N13—C13—C14177.6 (2)C2—C16—C17—C18177.3 (2)
O13B—N13—C13—C12179.3 (2)C21—C16—C17—C181.1 (4)
O13B—N13—C13—C141.6 (3)C2—C16—C21—C20177.1 (2)
N1—C2—C16—C1721.4 (4)C17—C16—C21—C200.6 (4)
N1—C2—C16—C21162.4 (2)C16—C17—C18—C190.7 (4)
N3—C2—C16—C17155.6 (2)C17—C18—C19—Br19179.9 (2)
N3—C2—C16—C2120.6 (4)C17—C18—C19—C200.2 (4)
C9—C4—C5—C60.2 (5)Br19—C19—C20—C21179.4 (2)
C5—C4—C9—N3179.2 (3)C18—C19—C20—C210.7 (4)
C5—C4—C9—C80.1 (4)C19—C20—C21—C160.3 (4)
C4—C5—C6—C70.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O13Bi0.932.563.491 (4)175
C12—H12···O13Aii0.932.513.312 (4)145
C15—H15···N3iii0.932.563.463 (3)165
C21—H21···N30.932.542.848 (4)100
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) x+2, y+1, z+1.
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds