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ISSN: 2056-9890

Bis[3-allyl-1-(4-cyano­benzyl)-2-methylbenzimidazolium] di-μ-bromido-bis­[bromidocuprate(I)]

aOrdered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China
*Correspondence e-mail: seuwangwei@gmail.com

(Received 13 August 2008; accepted 20 August 2008; online 23 August 2008)

The asymmetric unit of the title compound, (C19H18N3)2[Cu2Br4], contains one cation and one half-anion; there is a centre of symmetry mid-way between the two Cu atoms. In the cation, the nearly planar benzimidazole ring system is oriented at dihedral angles of 75.31 (3) and 21.39 (3)° with respect to the cyano­benzyl and allyl groups, respectively. The dihedral angle between cyano­benzyl and allyl groups is 87.94 (3)°. In the crystal structure, inter­molecular C—H⋯Br hydrogen bonds link the mol­ecules. There is a C—H⋯π contact between the cyano­benzyl ring and the anion; ππ contacts also exist between the benzimidazole ring systems as well as between the anion and the cyano­benzyl ring [centroid–centroid distances = 4.024 (1) and 4.617 (1) Å, respectively].

Related literature

For related literature, see: Aaker et al. (2005[Aaker, C. B., Desper, J. & Urbinam, J. F. (2005). Cryst. Growth Des. 5, 1283-1293.]).

[Scheme 1]

Experimental

Crystal data
  • (C19H18N3)2[Cu2Br4]

  • Mr = 1023.44

  • Triclinic, [P \overline 1]

  • a = 9.6407 (5) Å

  • b = 10.1029 (11) Å

  • c = 11.0389 (6) Å

  • α = 87.27 (2)°

  • β = 69.990 (17)°

  • γ = 81.41 (2)°

  • V = 998.93 (18) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 5.10 mm−1

  • T = 294 (2) K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Rigaku, SCXmini diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC. (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]) Tmin = 0.361, Tmax = 0.375

  • 10227 measured reflections

  • 4517 independent reflections

  • 2765 reflections with I > 2σ(I)

  • Rint = 0.052

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.134

  • S = 0.97

  • 4517 reflections

  • 226 parameters

  • H-atom parameters constrained

  • Δρmax = 1.06 e Å−3

  • Δρmin = −0.76 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8A⋯Br1i 0.97 2.90 3.863 (5) 175
C10—H10C⋯Br1 0.96 2.93 3.788 (5) 150
C17—H17A⋯Br1ii 0.93 2.92 3.707 (5) 143
C4—H4a⋯Cg1iii 0.93 3.36 3.746 (2) 108 (1)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1; (iii) x, y, z-1. Cg1 is the centroid of the anion.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC. (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005[Rigaku/MSC. (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The asymmetric unit of the title compound contains one cation and one-half anion (Fig. 1). In the cation, rings A (N2/N3/C9/C14/C19), B (C14—C19) and C (C2—C7) are, of course, planar and the dihedral angles between them are A/B = 1.47 (3)°, A/C = 75.18 (4)° and B/C = 75.46 (4)°. So, the benzimidazole ring system is nearly planar, and it is oriented with respect to the cyanobenzyl and allyl groups at dihedral angles of 75.31 (3)° and 21.39 (3)°, respectively. The dihedral angle between cyanobenzyl and allyl groups is 87.94 (3)°.

In the crystal structure, intermolecular C—H···Br hydrogen bonds link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure. There also exists a C—H···π contact (Table 1) between the cyanobenzyl ring and the anion. The ππ contacts between the rings A and B as well as the anion and the ring C, Cg2···Cg4i and Cg3···Cg1ii [symmetry codes: (i) -x, 1 - y, 1 - z; (ii) x, y, z - 1, where Cg1, Cg2, Cg3 and Cg4 are centroids of the anion, the rings A, C and B, respectively] further stabilize the structure, with centroid-centroid distances of 4.024 (1) and 4.617 (1) Å, respectively.

Related literature top

For related literature, see: Aaker et al. (2005). Cg1 is the centroid of the anion.

Experimental top

The synthesis of (1) (Scheme 1) was reported, previously (Aaker et al., 2005). The mixture of (1) (2.47 g, 10 mmol), allyl bromide (1.21 g, 10 mmol) and Na2CO3 (0.53 g, 5 mmol) was stirred in THF (50 ml) under reflux for 24 h to obtain (2) (Scheme 1) with high yield (90%). The colorless crystals suitable for X-ray analysis were obtained from the mixture of (2) (73.6 mg, 0.2 mmol), CuBr (28.8 mg, 0.2 mmol) and methanol (2 ml) sealed in a glass tube maintaining at 353 K for 5 d.

Refinement top

H atoms were positioned geometrically, with C—H = 0.93, 0.97 and 0.96 Å for aromatic and methylene (for allyl C13 atom), methylene and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level [symmetry code: (A) -x, 1 - y, 2 - z].
[Figure 2] Fig. 2. A partial packing diagram of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.
[Figure 3] Fig. 3. The formation of the title compound.
Bis[3-allyl-1-(4-cyanobenzyl)-2-methylbenzimidazolium] di-µ-bromido-bis[bromidocuprate(I)] top
Crystal data top
(C19H18N3)2[Cu2Br4]Z = 1
Mr = 1023.44F(000) = 504
Triclinic, P1Dx = 1.701 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6407 (5) ÅCell parameters from 2257 reflections
b = 10.1029 (11) Åθ = 2.8–27.5°
c = 11.0389 (6) ŵ = 5.10 mm1
α = 87.27 (2)°T = 294 K
β = 69.990 (17)°Prism, colorless
γ = 81.41 (2)°0.20 × 0.20 × 0.20 mm
V = 998.93 (18) Å3
Data collection top
Rigaku, SCXmini
diffractometer
4517 independent reflections
Radiation source: fine-focus sealed tube2765 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 2.8°
ω scansh = 1212
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 1313
Tmin = 0.361, Tmax = 0.375l = 1414
10227 measured reflections
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0636P)2]
where P = (Fo2 + 2Fc2)/3
4517 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 1.07 e Å3
0 restraintsΔρmin = 0.76 e Å3
Crystal data top
(C19H18N3)2[Cu2Br4]γ = 81.41 (2)°
Mr = 1023.44V = 998.93 (18) Å3
Triclinic, P1Z = 1
a = 9.6407 (5) ÅMo Kα radiation
b = 10.1029 (11) ŵ = 5.10 mm1
c = 11.0389 (6) ÅT = 294 K
α = 87.27 (2)°0.20 × 0.20 × 0.20 mm
β = 69.990 (17)°
Data collection top
Rigaku, SCXmini
diffractometer
4517 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
2765 reflections with I > 2σ(I)
Tmin = 0.361, Tmax = 0.375Rint = 0.052
10227 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.134H-atom parameters constrained
S = 0.97Δρmax = 1.07 e Å3
4517 reflectionsΔρmin = 0.76 e Å3
226 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
Br10.37052 (6)0.42643 (5)0.73582 (5)0.05337 (18)
Br20.06239 (6)0.34357 (6)0.94360 (6)0.0684 (2)
Cu10.14770 (8)0.47171 (8)0.90578 (7)0.0703 (3)
N10.5950 (7)0.0085 (5)0.2925 (5)0.0873 (18)
N20.2273 (4)0.3449 (4)0.3653 (4)0.0413 (9)
N30.1992 (4)0.2221 (4)0.5394 (3)0.0406 (9)
C10.5454 (7)0.0689 (6)0.1995 (6)0.0586 (14)
C20.4844 (6)0.1517 (5)0.0842 (5)0.0486 (12)
C30.3336 (6)0.1632 (5)0.0149 (5)0.0554 (14)
H3A0.27290.11480.03960.067*
C40.2729 (6)0.2476 (5)0.0920 (5)0.0511 (13)
H4A0.17140.25620.13860.061*
C50.3641 (5)0.3188 (5)0.1291 (4)0.0428 (11)
C60.5157 (5)0.3059 (5)0.0593 (5)0.0522 (13)
H6A0.57710.35290.08470.063*
C70.5758 (6)0.2230 (6)0.0484 (5)0.0551 (13)
H7A0.67700.21550.09600.066*
C80.2982 (6)0.4137 (5)0.2437 (4)0.0468 (12)
H8A0.37670.45800.25290.056*
H8B0.22460.48190.22740.056*
C90.2985 (5)0.2755 (5)0.4384 (4)0.0411 (11)
C100.4630 (5)0.2599 (6)0.4119 (5)0.0538 (13)
H10A0.50950.30720.33450.081*
H10B0.50340.16670.40140.081*
H10C0.48180.29590.48290.081*
C110.2307 (6)0.1405 (5)0.6424 (5)0.0511 (12)
H11A0.17530.18480.72430.061*
H11B0.33600.13470.63010.061*
C120.1921 (7)0.0028 (6)0.6483 (6)0.0634 (15)
H12A0.22000.04430.57130.076*
C130.1227 (9)0.0555 (7)0.7528 (8)0.105 (3)
H13C0.09320.01120.83140.126*
H13A0.10190.14210.74980.126*
C140.0569 (5)0.2589 (5)0.5305 (4)0.0397 (10)
C150.0827 (5)0.2331 (5)0.6120 (5)0.0496 (12)
H15A0.09470.18180.68610.060*
C160.2025 (6)0.2887 (6)0.5754 (5)0.0563 (14)
H16A0.29800.27380.62610.068*
C170.1844 (6)0.3659 (5)0.4657 (5)0.0539 (13)
H17A0.26860.40110.44560.065*
C180.0473 (5)0.3928 (5)0.3850 (5)0.0497 (12)
H18A0.03650.44490.31140.060*
C190.0746 (5)0.3368 (5)0.4208 (4)0.0404 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0453 (3)0.0604 (3)0.0527 (3)0.0150 (2)0.0116 (2)0.0021 (3)
Br20.0466 (3)0.0807 (4)0.0750 (4)0.0173 (3)0.0105 (3)0.0237 (3)
Cu10.0549 (5)0.0929 (6)0.0560 (4)0.0042 (4)0.0119 (3)0.0038 (4)
N10.114 (5)0.076 (4)0.059 (3)0.020 (3)0.007 (3)0.020 (3)
N20.037 (2)0.048 (2)0.037 (2)0.0122 (17)0.0077 (16)0.0018 (18)
N30.040 (2)0.047 (2)0.035 (2)0.0093 (17)0.0115 (17)0.0010 (18)
C10.071 (4)0.054 (3)0.053 (3)0.016 (3)0.021 (3)0.001 (3)
C20.061 (3)0.045 (3)0.039 (3)0.008 (2)0.015 (2)0.002 (2)
C30.068 (4)0.058 (3)0.052 (3)0.025 (3)0.029 (3)0.002 (3)
C40.044 (3)0.062 (3)0.046 (3)0.015 (2)0.011 (2)0.004 (3)
C50.049 (3)0.045 (3)0.036 (2)0.016 (2)0.013 (2)0.004 (2)
C60.039 (3)0.070 (4)0.049 (3)0.020 (2)0.011 (2)0.009 (3)
C70.046 (3)0.071 (4)0.046 (3)0.014 (3)0.010 (2)0.008 (3)
C80.051 (3)0.049 (3)0.038 (3)0.014 (2)0.010 (2)0.001 (2)
C90.042 (3)0.044 (3)0.039 (3)0.007 (2)0.014 (2)0.005 (2)
C100.037 (3)0.072 (4)0.053 (3)0.014 (2)0.013 (2)0.001 (3)
C110.050 (3)0.054 (3)0.055 (3)0.013 (2)0.023 (2)0.009 (3)
C120.075 (4)0.057 (3)0.060 (4)0.007 (3)0.027 (3)0.003 (3)
C130.132 (7)0.075 (5)0.116 (7)0.046 (5)0.041 (6)0.022 (5)
C140.035 (2)0.044 (3)0.039 (3)0.005 (2)0.0107 (19)0.007 (2)
C150.039 (3)0.056 (3)0.046 (3)0.005 (2)0.005 (2)0.002 (2)
C160.033 (3)0.068 (4)0.060 (3)0.009 (2)0.002 (2)0.010 (3)
C170.043 (3)0.059 (3)0.062 (3)0.003 (2)0.022 (3)0.004 (3)
C180.044 (3)0.057 (3)0.051 (3)0.006 (2)0.019 (2)0.002 (3)
C190.038 (3)0.040 (3)0.042 (3)0.007 (2)0.011 (2)0.006 (2)
Geometric parameters (Å, º) top
Br1—Cu12.3181 (10)C8—H8A0.9700
Br2—Cu1i2.4134 (11)C8—H8B0.9700
Br2—Cu12.4710 (10)C9—C101.496 (6)
Cu1—Br2i2.4134 (11)C10—H10A0.9600
Cu1—Cu1i2.8874 (15)C10—H10B0.9600
N1—C11.136 (7)C10—H10C0.9600
N2—C81.476 (6)C11—C121.486 (7)
N2—C91.340 (6)C11—H11A0.9700
N2—C191.401 (5)C11—H11B0.9700
N3—C91.347 (6)C12—C131.285 (8)
N3—C111.462 (6)C12—H12A0.9300
N3—C141.402 (6)C13—H13C0.9300
C2—C11.452 (7)C13—H13A0.9300
C2—C31.381 (7)C14—C151.394 (6)
C2—C71.381 (7)C15—H15A0.9300
C3—C41.392 (7)C16—C151.384 (7)
C3—H3A0.9300C16—C171.382 (7)
C4—H4A0.9300C16—H16A0.9300
C5—C41.385 (6)C17—H17A0.9300
C5—C61.389 (6)C18—C171.376 (7)
C5—C81.519 (6)C18—H18A0.9300
C6—H6A0.9300C19—C141.387 (6)
C7—C61.389 (7)C19—C181.398 (7)
C7—H7A0.9300
Cu1i—Br2—Cu172.46 (3)N2—C9—C10125.1 (4)
Br1—Cu1—Br2i129.22 (4)N3—C9—C10125.3 (4)
Br1—Cu1—Br2122.83 (4)C9—C10—H10A109.5
Br2i—Cu1—Br2107.54 (3)C9—C10—H10B109.5
Br1—Cu1—Cu1i172.96 (5)H10A—C10—H10B109.5
Br2i—Cu1—Cu1i54.69 (3)C9—C10—H10C109.5
Br2—Cu1—Cu1i52.85 (3)H10A—C10—H10C109.5
C9—N2—C19108.6 (4)H10B—C10—H10C109.5
C9—N2—C8125.8 (4)N3—C11—C12113.8 (4)
C19—N2—C8125.5 (4)N3—C11—H11A108.8
C9—N3—C14108.3 (4)C12—C11—H11A108.8
C9—N3—C11127.0 (4)N3—C11—H11B108.8
C14—N3—C11124.8 (4)C12—C11—H11B108.8
N1—C1—C2177.3 (6)H11A—C11—H11B107.7
C7—C2—C3120.7 (4)C13—C12—C11124.3 (6)
C7—C2—C1119.9 (5)C13—C12—H12A117.8
C3—C2—C1119.4 (5)C11—C12—H12A117.8
C2—C3—C4119.8 (5)C12—C13—H13C120.0
C2—C3—H3A120.1C12—C13—H13A120.0
C4—C3—H3A120.1H13C—C13—H13A120.0
C5—C4—C3119.9 (5)C19—C14—C15122.2 (4)
C5—C4—H4A120.1C19—C14—N3106.8 (4)
C3—C4—H4A120.1C15—C14—N3130.9 (5)
C4—C5—C6119.9 (4)C16—C15—C14115.7 (5)
C4—C5—C8120.3 (4)C16—C15—H15A122.2
C6—C5—C8119.8 (4)C14—C15—H15A122.2
C7—C6—C5120.1 (4)C17—C16—C15121.9 (5)
C7—C6—H6A119.9C17—C16—H16A119.0
C5—C6—H6A119.9C15—C16—H16A119.0
C2—C7—C6119.6 (5)C18—C17—C16122.9 (5)
C2—C7—H7A120.2C18—C17—H17A118.5
C6—C7—H7A120.2C16—C17—H17A118.5
N2—C8—C5112.7 (4)C17—C18—C19115.6 (5)
N2—C8—H8A109.0C17—C18—H18A122.2
C5—C8—H8A109.0C19—C18—H18A122.2
N2—C8—H8B109.0C14—C19—C18121.6 (4)
C5—C8—H8B109.0C14—C19—N2106.7 (4)
H8A—C8—H8B107.8C18—C19—N2131.7 (4)
N2—C9—N3109.6 (4)
Cu1i—Br2—Cu1—Br1173.22 (6)C7—C2—C3—C40.1 (8)
Cu1i—Br2—Cu1—Br2i0.0C1—C2—C7—C6177.6 (5)
C9—N2—C8—C579.9 (6)C3—C2—C7—C60.7 (8)
C19—N2—C8—C597.3 (5)C2—C3—C4—C50.5 (8)
C8—N2—C9—N3177.6 (4)C6—C5—C4—C30.1 (8)
C19—N2—C9—N30.0 (5)C8—C5—C4—C3178.5 (5)
C8—N2—C9—C102.5 (7)C4—C5—C6—C70.7 (8)
C19—N2—C9—C10179.9 (4)C8—C5—C6—C7177.7 (5)
C8—N2—C19—C14177.4 (4)C4—C5—C8—N261.6 (6)
C9—N2—C19—C140.2 (5)C6—C5—C8—N2119.9 (5)
C8—N2—C19—C183.9 (8)C2—C7—C6—C51.1 (8)
C9—N2—C19—C18178.5 (5)N3—C11—C12—C13135.1 (7)
C11—N3—C9—N2179.4 (4)N3—C14—C15—C16178.1 (5)
C14—N3—C9—N20.2 (5)C19—C14—C15—C160.8 (7)
C11—N3—C9—C100.5 (7)C15—C16—C17—C180.2 (8)
C14—N3—C9—C10179.9 (5)C17—C16—C15—C140.6 (8)
C9—N3—C11—C12117.9 (5)N2—C19—C14—N30.3 (5)
C14—N3—C11—C1262.6 (6)N2—C19—C14—C15178.1 (4)
C9—N3—C14—C15177.9 (5)C18—C19—C14—N3178.5 (4)
C11—N3—C14—C151.7 (8)C18—C19—C14—C150.7 (7)
C9—N3—C14—C190.3 (5)C19—C18—C17—C160.0 (8)
C11—N3—C14—C19179.3 (4)N2—C19—C18—C17178.3 (5)
C1—C2—C3—C4176.8 (5)C14—C19—C18—C170.2 (7)
Symmetry code: (i) x, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···Br1ii0.972.903.863 (5)175
C10—H10C···Br10.962.933.788 (5)150
C17—H17A···Br1iii0.932.923.707 (5)143
C4—H4a···Cg1iv0.933.363.746 (2)108 (1)
Symmetry codes: (ii) x+1, y+1, z+1; (iii) x, y+1, z+1; (iv) x, y, z1.

Experimental details

Crystal data
Chemical formula(C19H18N3)2[Cu2Br4]
Mr1023.44
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)9.6407 (5), 10.1029 (11), 11.0389 (6)
α, β, γ (°)87.27 (2), 69.990 (17), 81.41 (2)
V3)998.93 (18)
Z1
Radiation typeMo Kα
µ (mm1)5.10
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerRigaku, SCXmini
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.361, 0.375
No. of measured, independent and
observed [I > 2σ(I)] reflections
10227, 4517, 2765
Rint0.052
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.134, 0.97
No. of reflections4517
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.07, 0.76

Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalStructure (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···Br1i0.972.903.863 (5)175.0
C10—H10C···Br10.962.933.788 (5)149.9
C17—H17A···Br1ii0.932.923.707 (5)143.4
C4—H4a···Cg1iii0.933.363.746 (2)107.5 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1; (iii) x, y, z1.
 

Acknowledgements

The authors are grateful to the Starter Fund of Southeast University for financial support to purchase the CCD X-ray diffractometer.

References

First citationAaker, C. B., Desper, J. & Urbinam, J. F. (2005). Cryst. Growth Des. 5, 1283–1293.  Google Scholar
First citationRigaku/MSC. (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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