PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2826.
Published online 2009 October 23. doi:  10.1107/S1600536809042883
PMCID: PMC2971065

N-[2-(2-Bromo­benzyl­amino)phen­yl]-N-butylformamide

Abstract

The title compound, C18H21BrN2O, crystallizes with two mol­ecules (A and B) in the asymmetric unit (Z′ = 2). The major differences between the two mol­ecules are related to the conformations adopted by their n-butyl side chains. The phenyl rings in both mol­ecules are almost perpendicular, making dihedral angles of 79.2 (3) and 80.8 (3)°. The amide units are planar (r.m.s. deviations of 0.0018 and 0.021 Å) and almost perpendicular to the phenyl rings to which they are attached [dihedral angles of 68.9 (4) and 71.1 (4)°]. In the crystal, molecules A and B each form only an intermolecular N—H(...)O hydrogen bond with an adjacent molecule of the same kind. There are no significant intermolecular interactions between molecules A and B.

Related literature

For a related structure, see: Manjare et al. (2009 [triangle]). For related synthetic studies, see: Albéniz et al. (2002 [triangle]); Denk et al. (2001 [triangle]); Jarrar & Fataftah (1977 [triangle]); Çetinkaya et al. (1998 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2826-scheme1.jpg

Experimental

Crystal data

  • C18H21BrN2O
  • M r = 361.28
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2826-efi1.jpg
  • a = 8.7067 (4) Å
  • b = 10.8208 (6) Å
  • c = 19.7480 (13) Å
  • α = 87.180 (5)°
  • β = 82.622 (5)°
  • γ = 66.706 (5)°
  • V = 1694.72 (17) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.43 mm−1
  • T = 200 K
  • 0.49 × 0.28 × 0.23 mm

Data collection

  • Oxford Diffraction Gemini R diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 [triangle]) T min = 0.478, T max = 1.000
  • 13877 measured reflections
  • 5942 independent reflections
  • 3799 reflections with I > 2σ(I)
  • R int = 0.049

Refinement

  • R[F 2 > 2σ(F 2)] = 0.095
  • wR(F 2) = 0.252
  • S = 1.10
  • 5942 reflections
  • 399 parameters
  • H-atom parameters constrained
  • Δρmax = 1.94 e Å−3
  • Δρmin = −0.82 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809042883/ds2009sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042883/ds2009Isup2.hkl

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

Acknowledgments

HBS is grateful to the Department of Science and Technology (DST) for the award of a Ramanna Fellowship. STM thanks the CSIR for a JRF/SRF fellowship. RJB wishes to acknowledge the NSF–MRI program (grant CHE-0619278) for funds to purchase the diffractometer.

supplementary crystallographic information

Comment

The structure of the title compound, (I), is shown below. Dimensions are available in the archived CIF.

The title compound, C18H21BrN2O, was obtained as a hydrolysis product during an attempted synthesis of the butyl substituted thiocarbene compound from the corresponding benzimidazolium salt (see Fig. 3). The compound crystallizes with two molecules in the asymmetric unit (Z' = 2). The major differences between the two molecules are related to the conformations adopted by the n-butyl substituents. This is shown most clearly by a comparison of the n-butyl torsion angles. In molecule A the torsion angles for N1A—C15A—C16A—C17A and C15A—C16A—C17A—C18A are 69.2 (11) and 66.8 (13)° while for molecule B the corresponding angles are 176.50 (10) and -61.8 (17)°.

The two phenyl rings in A and B make dihedral angles of 79.2 (3) and 80.8 (3), respectively with each other. Both molecules A and B form only an intermolecular N–H···O hydrogen bond with an adjoining molecule of the same kind. There are no significant intermolecular interactions between molecule A and B. The atoms making up the amide group for both A and B are planar (r.m.s. deviation of fitted atoms 0.0018 and 0.021 Å respectively) and both groups are almost perpendicular to the plane of the phenyl ring to which they are attached (dihedral angles of 68.9 (4) and 71.1 (4)° respectively).

While there has only been one structure reported for a related molecule (Manjare et al. 2009), there have been several synthetic studies reported (Jarrar & Fataftah, 1977; Denk et al. 2001; Çetinkaya et al. 1998; Albéniz et al. 2002).

Experimental

The benzylimidazoylium salt 2 (1.0 mmol) was added to the solution of Na2S2 (2.0 mmol) at room temperature under nitrogen atmosphere and the reaction mixture was stirred for 6–10 h at room temperature as shown in scheme 1. Then KOtBu (1.0 mmol) was added to the reaction mixture and stirred further for 5–7 h. After completion of reaction, the reaction was quenched by adding water (50 ml), and extracted with dichloromethane, dried over Na2SO4, and evaporated. The residue obtained was dissolved in toluene and small amount of petroleum ether (60–80 °C) was added to separate the residue from the solution. The solution was filtered and evaporated; the residue was dissolved in diethyl ether and a small amount of petroleum ether (60–80 °C) was added and the solution was kept on table to afford X-ray quality crystals of 1 as a minor product.

Refinement

The crystal was weakly diffracting and no meaningful data could be obtained above a 2-theta of 50° so a high resolution cutoff was carried out with a threshold of d = 0.835. H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distances of 0.95 and 0.99 Å Uiso(H) = 1.2Ueq(C) = [1.5Ueq(CH3)]. The H attached to N was idealized with a distance of 0.88 Å. In the final difference Fourier there was a peak of 1.94 e/Å3 close to the Br atom.

Figures

Fig. 1.
The molecular structure of C18H21BrN2O the showing the atom numbering scheme and 50% probability displacement ellipsoids.
Fig. 2.
The molecular packing for C18H21BrN2O viewed down the b axis. The hydrogen bonding between N—H···N is shown by dashed lines.
Fig. 3.
Preparation of the title compound.

Crystal data

C18H21BrN2OZ = 4
Mr = 361.28F(000) = 744
Triclinic, P1Dx = 1.416 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.7067 (4) ÅCell parameters from 5504 reflections
b = 10.8208 (6) Åθ = 4.6–34.7°
c = 19.7480 (13) ŵ = 2.43 mm1
α = 87.180 (5)°T = 200 K
β = 82.622 (5)°Thick needle, colorless
γ = 66.706 (5)°0.49 × 0.28 × 0.23 mm
V = 1694.72 (17) Å3

Data collection

Oxford Diffraction Gemini R diffractometer5942 independent reflections
Radiation source: Enhance (Mo) X-ray Source3799 reflections with I > 2σ(I)
graphiteRint = 0.049
Detector resolution: 10.5081 pixels mm-1θmax = 25.2°, θmin = 4.6°
ω scansh = −10→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)k = −12→12
Tmin = 0.478, Tmax = 1.000l = −20→23
13877 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)] = 0.095Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.252H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.088P)2 + 17.292P] where P = (Fo2 + 2Fc2)/3
5942 reflections(Δ/σ)max < 0.001
399 parametersΔρmax = 1.94 e Å3
0 restraintsΔρmin = −0.81 e Å3

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
Br1A0.37929 (12)1.19458 (9)0.60470 (6)0.0425 (3)
O1A1.2053 (8)0.4014 (6)0.4756 (4)0.0476 (19)
N1A1.1593 (9)0.6243 (7)0.4840 (4)0.0288 (16)
N2A0.8719 (8)0.8358 (7)0.5427 (4)0.0299 (17)
H2AA0.86830.76710.52180.036*
C1A1.2027 (11)0.4980 (8)0.5061 (5)0.033 (2)
H1AA1.23550.48100.55090.039*
C2A1.1740 (10)0.7226 (8)0.5264 (5)0.0264 (19)
C3A1.3288 (11)0.7153 (9)0.5390 (5)0.031 (2)
H3AA1.42690.64250.52020.037*
C4A1.3465 (12)0.8090 (10)0.5775 (5)0.041 (2)
H4AA1.45490.80130.58600.050*
C5A1.2051 (13)0.9140 (9)0.6036 (5)0.037 (2)
H5AA1.21650.98000.63020.044*
C6A1.0472 (12)0.9271 (9)0.5925 (5)0.033 (2)
H6AA0.95181.00230.61100.040*
C7A1.0242 (10)0.8308 (8)0.5541 (4)0.0233 (18)
C8A0.7142 (11)0.9480 (9)0.5629 (5)0.032 (2)
H8AA0.62920.94680.53440.039*
H8AB0.73081.03270.55300.039*
C9A0.6447 (10)0.9492 (8)0.6369 (5)0.0285 (19)
C10A0.4963 (11)1.0512 (9)0.6642 (5)0.032 (2)
C11A0.4255 (13)1.0523 (12)0.7299 (5)0.045 (3)
H11A0.32351.12410.74640.054*
C12A0.5068 (16)0.9449 (14)0.7730 (5)0.059 (3)
H12A0.45880.94250.81880.070*
C13A0.6551 (16)0.8438 (13)0.7486 (6)0.056 (3)
H13A0.71140.77150.77750.067*
C14A0.7229 (13)0.8476 (10)0.6812 (5)0.038 (2)
H14A0.82700.77760.66510.046*
C15A1.1081 (11)0.6630 (9)0.4164 (5)0.032 (2)
H15A1.00370.74580.42020.039*
H15B1.08190.59100.39800.039*
C16A1.2394 (13)0.6877 (10)0.3668 (6)0.045 (2)
H16A1.27360.75270.38780.054*
H16B1.18710.73070.32550.054*
C17A1.3970 (14)0.5643 (12)0.3448 (6)0.050 (3)
H17A1.48040.59430.31820.060*
H17B1.44620.51800.38610.060*
C18A1.3692 (18)0.4668 (14)0.3032 (7)0.074 (4)
H18A1.47790.39570.28700.111*
H18B1.31220.51300.26400.111*
H18C1.29910.42690.33120.111*
Br1B0.13415 (14)0.30839 (10)0.89286 (6)0.0507 (4)
O1B0.1010 (8)1.1026 (6)1.0104 (4)0.0420 (17)
N2B0.2350 (10)0.6702 (8)0.9504 (5)0.043 (2)
H2BA0.15160.74040.97000.051*
N1B0.2818 (10)0.8840 (8)1.0051 (4)0.0367 (19)
C1B0.2085 (12)1.0049 (9)0.9810 (6)0.040 (2)
H1B0.24381.01800.93470.048*
C2B0.4187 (11)0.7787 (9)0.9663 (4)0.029 (2)
C3B0.5739 (12)0.7863 (10)0.9563 (5)0.040 (2)
H3BA0.58850.86030.97410.048*
C4B0.7098 (13)0.6858 (11)0.9199 (6)0.046 (3)
H4BA0.81760.68990.91270.056*
C5B0.6836 (12)0.5805 (11)0.8948 (5)0.045 (3)
H5BA0.77500.51020.87040.054*
C6B0.5278 (12)0.5753 (10)0.9044 (5)0.040 (2)
H6BA0.51350.50160.88590.048*
C7B0.3897 (11)0.6742 (9)0.9403 (5)0.034 (2)
C8B0.1972 (13)0.5605 (10)0.9317 (5)0.042 (2)
H8BA0.09300.56490.96020.051*
H8BB0.28920.47580.94320.051*
C9B0.1733 (11)0.5527 (10)0.8569 (5)0.039 (2)
C10B0.1435 (11)0.4489 (9)0.8321 (5)0.036 (2)
C11B0.1136 (14)0.4417 (12)0.7659 (6)0.052 (3)
H11B0.09090.36850.75180.063*
C12B0.1169 (16)0.5430 (14)0.7193 (7)0.063 (3)
H12B0.09890.53960.67310.076*
C13B0.1474 (15)0.6475 (14)0.7431 (6)0.061 (4)
H13B0.14700.71850.71280.074*
C14B0.1787 (14)0.6529 (11)0.8103 (7)0.055 (3)
H14B0.20390.72480.82430.066*
C15B0.2170 (14)0.8513 (11)1.0754 (5)0.046 (3)
H15C0.09600.90901.08580.055*
H15D0.22950.75621.07680.055*
C16B0.3143 (18)0.8742 (17)1.1276 (7)0.074 (4)
H16C0.30790.96771.12410.089*
H16D0.43420.81221.11890.089*
C17B0.240 (2)0.8494 (17)1.2001 (7)0.077 (4)
H17C0.24730.75561.20280.093*
H17D0.30880.85961.23380.093*
C18B0.064 (2)0.9411 (16)1.2183 (7)0.089 (5)
H18D0.01990.91321.26190.133*
H18E−0.00340.93851.18270.133*
H18F0.05761.03291.22260.133*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br1A0.0302 (5)0.0275 (5)0.0621 (8)−0.0027 (4)−0.0057 (5)−0.0033 (5)
O1A0.040 (4)0.016 (3)0.083 (6)−0.009 (3)0.007 (4)−0.015 (3)
N1A0.025 (4)0.020 (4)0.039 (5)−0.005 (3)−0.006 (3)−0.001 (3)
N2A0.022 (3)0.020 (4)0.043 (5)−0.004 (3)0.003 (3)−0.008 (3)
C1A0.029 (5)0.023 (5)0.043 (6)−0.010 (4)0.006 (4)−0.003 (4)
C2A0.023 (4)0.021 (4)0.033 (5)−0.008 (3)0.000 (4)0.004 (4)
C3A0.029 (5)0.026 (5)0.036 (5)−0.010 (4)−0.005 (4)0.004 (4)
C4A0.035 (5)0.048 (6)0.049 (6)−0.022 (5)−0.015 (5)0.007 (5)
C5A0.051 (6)0.032 (5)0.039 (6)−0.030 (5)−0.002 (5)0.000 (4)
C6A0.042 (5)0.022 (4)0.037 (6)−0.013 (4)−0.008 (4)0.000 (4)
C7A0.027 (4)0.016 (4)0.027 (5)−0.008 (3)−0.004 (4)0.000 (3)
C8A0.025 (4)0.023 (4)0.042 (6)−0.004 (4)0.004 (4)−0.011 (4)
C9A0.025 (4)0.024 (4)0.038 (5)−0.012 (4)0.001 (4)−0.002 (4)
C10A0.027 (4)0.028 (5)0.041 (6)−0.011 (4)−0.003 (4)−0.002 (4)
C11A0.033 (5)0.059 (7)0.038 (6)−0.015 (5)0.007 (5)−0.013 (5)
C12A0.066 (8)0.098 (10)0.021 (6)−0.045 (8)0.008 (5)−0.007 (6)
C13A0.062 (7)0.061 (7)0.049 (7)−0.029 (6)−0.016 (6)0.018 (6)
C14A0.041 (5)0.032 (5)0.038 (6)−0.010 (4)−0.009 (4)0.010 (4)
C15A0.033 (5)0.028 (5)0.027 (5)−0.002 (4)−0.005 (4)−0.007 (4)
C16A0.048 (6)0.035 (5)0.046 (7)−0.012 (5)−0.001 (5)0.000 (5)
C17A0.047 (6)0.055 (7)0.042 (7)−0.015 (5)0.002 (5)−0.007 (5)
C18A0.082 (10)0.067 (9)0.063 (9)−0.023 (8)0.022 (7)−0.035 (7)
Br1B0.0518 (7)0.0338 (6)0.0641 (8)−0.0140 (5)−0.0099 (6)0.0050 (5)
O1B0.037 (4)0.019 (3)0.064 (5)−0.004 (3)−0.009 (3)−0.006 (3)
N2B0.028 (4)0.034 (5)0.059 (6)−0.004 (4)−0.002 (4)−0.011 (4)
N1B0.038 (4)0.032 (4)0.026 (4)0.000 (4)−0.001 (3)0.004 (3)
C1B0.032 (5)0.031 (5)0.060 (7)−0.012 (5)−0.013 (5)0.002 (5)
C2B0.031 (5)0.029 (5)0.020 (5)−0.004 (4)−0.004 (4)0.007 (4)
C3B0.040 (5)0.040 (6)0.038 (6)−0.013 (5)−0.006 (4)0.002 (4)
C4B0.030 (5)0.060 (7)0.046 (7)−0.016 (5)−0.004 (5)0.010 (5)
C5B0.027 (5)0.047 (6)0.040 (6)0.007 (4)−0.004 (4)0.007 (5)
C6B0.038 (5)0.029 (5)0.045 (6)−0.005 (4)0.000 (5)−0.007 (4)
C7B0.029 (5)0.024 (5)0.038 (6)−0.002 (4)0.001 (4)0.001 (4)
C8B0.036 (5)0.039 (6)0.050 (7)−0.014 (5)−0.001 (5)0.008 (5)
C9B0.025 (5)0.037 (5)0.048 (6)−0.005 (4)−0.003 (4)0.009 (5)
C10B0.027 (5)0.032 (5)0.040 (6)−0.002 (4)0.001 (4)0.001 (4)
C11B0.045 (6)0.046 (6)0.051 (7)−0.002 (5)−0.001 (5)−0.010 (5)
C12B0.058 (8)0.069 (9)0.045 (7)−0.006 (7)−0.005 (6)0.008 (6)
C13B0.054 (7)0.068 (8)0.045 (7)−0.010 (6)−0.005 (6)0.034 (6)
C14B0.042 (6)0.047 (7)0.071 (9)−0.015 (5)−0.005 (6)0.022 (6)
C15B0.046 (6)0.048 (6)0.040 (6)−0.014 (5)−0.002 (5)−0.007 (5)
C16B0.070 (9)0.110 (12)0.056 (8)−0.048 (9)−0.012 (7)−0.014 (8)
C17B0.098 (11)0.099 (11)0.044 (8)−0.048 (10)−0.016 (8)0.018 (7)
C18B0.111 (13)0.082 (11)0.049 (9)−0.020 (10)0.018 (8)−0.007 (7)

Geometric parameters (Å, °)

Br1A—C10A1.925 (9)Br1B—C10B1.910 (10)
O1A—C1A1.224 (11)O1B—C1B1.212 (12)
N1A—C1A1.333 (11)N2B—C7B1.354 (12)
N1A—C2A1.440 (11)N2B—C8B1.427 (13)
N1A—C15A1.452 (11)N2B—H2BA0.8800
N2A—C7A1.353 (11)N1B—C1B1.305 (12)
N2A—C8A1.452 (11)N1B—C2B1.443 (12)
N2A—H2AA0.8800N1B—C15B1.509 (13)
C1A—H1AA0.9500C1B—H1B0.9500
C2A—C3A1.373 (12)C2B—C3B1.374 (13)
C2A—C7A1.429 (12)C2B—C7B1.388 (13)
C3A—C4A1.365 (13)C3B—C4B1.393 (15)
C3A—H3AA0.9500C3B—H3BA0.9500
C4A—C5A1.364 (14)C4B—C5B1.373 (16)
C4A—H4AA0.9500C4B—H4BA0.9500
C5A—C6A1.370 (13)C5B—C6B1.368 (14)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—C7A1.409 (12)C6B—C7B1.389 (13)
C6A—H6AA0.9500C6B—H6BA0.9500
C8A—C9A1.507 (13)C8B—C9B1.528 (15)
C8A—H8AA0.9900C8B—H8BA0.9900
C8A—H8AB0.9900C8B—H8BB0.9900
C9A—C14A1.380 (12)C9B—C10B1.373 (14)
C9A—C10A1.389 (12)C9B—C14B1.399 (14)
C10A—C11A1.362 (14)C10B—C11B1.378 (15)
C11A—C12A1.408 (17)C11B—C12B1.403 (17)
C11A—H11A0.9500C11B—H11B0.9500
C12A—C13A1.368 (17)C12B—C13B1.375 (19)
C12A—H12A0.9500C12B—H12B0.9500
C13A—C14A1.391 (15)C13B—C14B1.396 (17)
C13A—H13A0.9500C13B—H13B0.9500
C14A—H14A0.9500C14B—H14B0.9500
C15A—C16A1.505 (14)C15B—C16B1.502 (16)
C15A—H15A0.9900C15B—H15C0.9900
C15A—H15B0.9900C15B—H15D0.9900
C16A—C17A1.520 (14)C16B—C17B1.550 (18)
C16A—H16A0.9900C16B—H16C0.9900
C16A—H16B0.9900C16B—H16D0.9900
C17A—C18A1.478 (17)C17B—C18B1.47 (2)
C17A—H17A0.9900C17B—H17C0.9900
C17A—H17B0.9900C17B—H17D0.9900
C18A—H18A0.9800C18B—H18D0.9800
C18A—H18B0.9800C18B—H18E0.9800
C18A—H18C0.9800C18B—H18F0.9800
C1A—N1A—C2A119.2 (8)C7B—N2B—C8B124.9 (8)
C1A—N1A—C15A121.5 (8)C7B—N2B—H2BA117.6
C2A—N1A—C15A119.2 (7)C8B—N2B—H2BA117.6
C7A—N2A—C8A123.7 (7)C1B—N1B—C2B122.6 (8)
C7A—N2A—H2AA118.1C1B—N1B—C15B118.8 (9)
C8A—N2A—H2AA118.1C2B—N1B—C15B118.6 (7)
O1A—C1A—N1A127.6 (10)O1B—C1B—N1B128.1 (11)
O1A—C1A—H1AA116.2O1B—C1B—H1B115.9
N1A—C1A—H1AA116.2N1B—C1B—H1B115.9
C3A—C2A—C7A120.1 (8)C3B—C2B—C7B122.3 (9)
C3A—C2A—N1A121.0 (8)C3B—C2B—N1B118.4 (9)
C7A—C2A—N1A118.9 (7)C7B—C2B—N1B119.3 (8)
C4A—C3A—C2A122.2 (9)C2B—C3B—C4B120.2 (10)
C4A—C3A—H3AA118.9C2B—C3B—H3BA119.9
C2A—C3A—H3AA118.9C4B—C3B—H3BA119.9
C5A—C4A—C3A118.5 (9)C5B—C4B—C3B118.2 (9)
C5A—C4A—H4AA120.8C5B—C4B—H4BA120.9
C3A—C4A—H4AA120.8C3B—C4B—H4BA120.9
C4A—C5A—C6A122.0 (9)C6B—C5B—C4B121.0 (10)
C4A—C5A—H5AA119.0C6B—C5B—H5BA119.5
C6A—C5A—H5AA119.0C4B—C5B—H5BA119.5
C5A—C6A—C7A121.0 (9)C5B—C6B—C7B122.2 (10)
C5A—C6A—H6AA119.5C5B—C6B—H6BA118.9
C7A—C6A—H6AA119.5C7B—C6B—H6BA118.9
N2A—C7A—C6A124.0 (8)N2B—C7B—C2B121.0 (8)
N2A—C7A—C2A119.8 (7)N2B—C7B—C6B122.9 (9)
C6A—C7A—C2A116.2 (8)C2B—C7B—C6B116.2 (9)
N2A—C8A—C9A115.2 (8)N2B—C8B—C9B116.8 (8)
N2A—C8A—H8AA108.5N2B—C8B—H8BA108.1
C9A—C8A—H8AA108.5C9B—C8B—H8BA108.1
N2A—C8A—H8AB108.5N2B—C8B—H8BB108.1
C9A—C8A—H8AB108.5C9B—C8B—H8BB108.1
H8AA—C8A—H8AB107.5H8BA—C8B—H8BB107.3
C14A—C9A—C10A116.1 (9)C10B—C9B—C14B116.6 (10)
C14A—C9A—C8A121.9 (8)C10B—C9B—C8B122.2 (9)
C10A—C9A—C8A122.0 (8)C14B—C9B—C8B121.2 (10)
C11A—C10A—C9A123.6 (9)C9B—C10B—C11B123.8 (10)
C11A—C10A—Br1A118.2 (7)C9B—C10B—Br1B119.0 (8)
C9A—C10A—Br1A118.1 (7)C11B—C10B—Br1B117.2 (8)
C10A—C11A—C12A118.6 (10)C10B—C11B—C12B119.6 (12)
C10A—C11A—H11A120.7C10B—C11B—H11B120.2
C12A—C11A—H11A120.7C12B—C11B—H11B120.2
C13A—C12A—C11A119.8 (10)C13B—C12B—C11B117.3 (12)
C13A—C12A—H12A120.1C13B—C12B—H12B121.3
C11A—C12A—H12A120.1C11B—C12B—H12B121.3
C12A—C13A—C14A119.5 (11)C12B—C13B—C14B122.4 (11)
C12A—C13A—H13A120.2C12B—C13B—H13B118.8
C14A—C13A—H13A120.2C14B—C13B—H13B118.8
C9A—C14A—C13A122.4 (10)C13B—C14B—C9B120.2 (12)
C9A—C14A—H14A118.8C13B—C14B—H14B119.9
C13A—C14A—H14A118.8C9B—C14B—H14B119.9
N1A—C15A—C16A113.6 (8)C16B—C15B—N1B109.8 (9)
N1A—C15A—H15A108.9C16B—C15B—H15C109.7
C16A—C15A—H15A108.9N1B—C15B—H15C109.7
N1A—C15A—H15B108.9C16B—C15B—H15D109.7
C16A—C15A—H15B108.9N1B—C15B—H15D109.7
H15A—C15A—H15B107.7H15C—C15B—H15D108.2
C15A—C16A—C17A116.0 (8)C15B—C16B—C17B109.6 (11)
C15A—C16A—H16A108.3C15B—C16B—H16C109.8
C17A—C16A—H16A108.3C17B—C16B—H16C109.8
C15A—C16A—H16B108.3C15B—C16B—H16D109.8
C17A—C16A—H16B108.3C17B—C16B—H16D109.8
H16A—C16A—H16B107.4H16C—C16B—H16D108.2
C18A—C17A—C16A114.6 (10)C18B—C17B—C16B113.4 (12)
C18A—C17A—H17A108.6C18B—C17B—H17C108.9
C16A—C17A—H17A108.6C16B—C17B—H17C108.9
C18A—C17A—H17B108.6C18B—C17B—H17D108.9
C16A—C17A—H17B108.6C16B—C17B—H17D108.9
H17A—C17A—H17B107.6H17C—C17B—H17D107.7
C17A—C18A—H18A109.5C17B—C18B—H18D109.5
C17A—C18A—H18B109.5C17B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
C17A—C18A—H18C109.5C17B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
C2A—N1A—C1A—O1A−176.4 (8)C2B—N1B—C1B—O1B−174.7 (9)
C15A—N1A—C1A—O1A−0.5 (14)C15B—N1B—C1B—O1B7.6 (15)
C1A—N1A—C2A—C3A67.9 (11)C1B—N1B—C2B—C3B72.6 (12)
C15A—N1A—C2A—C3A−108.1 (9)C15B—N1B—C2B—C3B−109.6 (10)
C1A—N1A—C2A—C7A−113.6 (9)C1B—N1B—C2B—C7B−107.1 (11)
C15A—N1A—C2A—C7A70.4 (10)C15B—N1B—C2B—C7B70.7 (11)
C7A—C2A—C3A—C4A−0.1 (14)C7B—C2B—C3B—C4B−1.2 (15)
N1A—C2A—C3A—C4A178.3 (8)N1B—C2B—C3B—C4B179.1 (9)
C2A—C3A—C4A—C5A−0.8 (14)C2B—C3B—C4B—C5B0.1 (15)
C3A—C4A—C5A—C6A0.4 (15)C3B—C4B—C5B—C6B0.9 (16)
C4A—C5A—C6A—C7A0.8 (14)C4B—C5B—C6B—C7B−0.8 (16)
C8A—N2A—C7A—C6A6.4 (14)C8B—N2B—C7B—C2B−173.3 (9)
C8A—N2A—C7A—C2A−173.7 (8)C8B—N2B—C7B—C6B6.0 (16)
C5A—C6A—C7A—N2A178.2 (9)C3B—C2B—C7B—N2B−179.3 (9)
C5A—C6A—C7A—C2A−1.6 (12)N1B—C2B—C7B—N2B0.4 (13)
C3A—C2A—C7A—N2A−178.6 (8)C3B—C2B—C7B—C6B1.4 (14)
N1A—C2A—C7A—N2A2.9 (12)N1B—C2B—C7B—C6B−179.0 (8)
C3A—C2A—C7A—C6A1.3 (12)C5B—C6B—C7B—N2B−179.7 (10)
N1A—C2A—C7A—C6A−177.2 (8)C5B—C6B—C7B—C2B−0.4 (15)
C7A—N2A—C8A—C9A−80.4 (10)C7B—N2B—C8B—C9B−80.8 (12)
N2A—C8A—C9A—C14A−2.5 (12)N2B—C8B—C9B—C10B177.2 (9)
N2A—C8A—C9A—C10A178.9 (8)N2B—C8B—C9B—C14B−3.6 (14)
C14A—C9A—C10A—C11A−2.0 (13)C14B—C9B—C10B—C11B−2.4 (14)
C8A—C9A—C10A—C11A176.7 (9)C8B—C9B—C10B—C11B176.9 (9)
C14A—C9A—C10A—Br1A−179.1 (6)C14B—C9B—C10B—Br1B−180.0 (7)
C8A—C9A—C10A—Br1A−0.3 (11)C8B—C9B—C10B—Br1B−0.7 (12)
C9A—C10A—C11A—C12A0.3 (15)C9B—C10B—C11B—C12B1.6 (16)
Br1A—C10A—C11A—C12A177.4 (8)Br1B—C10B—C11B—C12B179.3 (8)
C10A—C11A—C12A—C13A1.1 (16)C10B—C11B—C12B—C13B−1.2 (17)
C11A—C12A—C13A—C14A−0.8 (17)C11B—C12B—C13B—C14B1.8 (18)
C10A—C9A—C14A—C13A2.4 (14)C12B—C13B—C14B—C9B−2.6 (18)
C8A—C9A—C14A—C13A−176.4 (9)C10B—C9B—C14B—C13B2.8 (15)
C12A—C13A—C14A—C9A−1.1 (17)C8B—C9B—C14B—C13B−176.5 (10)
C1A—N1A—C15A—C16A−106.0 (9)C1B—N1B—C15B—C16B−93.1 (12)
C2A—N1A—C15A—C16A69.9 (10)C2B—N1B—C15B—C16B89.0 (12)
N1A—C15A—C16A—C17A69.3 (11)N1B—C15B—C16B—C17B176.4 (11)
C15A—C16A—C17A—C18A66.8 (14)C15B—C16B—C17B—C18B−61.8 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2A—H2AA···O1Ai0.882.152.947 (9)150
N2B—H2BA···O1Bii0.882.183.020 (10)159

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DS2009).

References

  • Albéniz, A. C., Espinet, P., Manrique, R. & Pérez-Mateo, A. (2002). Angew. Chem. Int. Ed.41, 2363–2366. [PubMed]
  • Çetinkaya, B., Çetinkaya, E., Chamizo, J. A., Hitchcock, P. B., Jasaim, H. A., Küçükbay, H. & Lappert, M. F. (1998). J. Chem Soc. Perkin Trans 1, pp. 2047–2054.
  • Denk, M. K., Rodezno, J. M., Gupta, S. & Lough, L. J. (2001). J. Organomet. Chem.617, 242–253.
  • Jarrar, A. A. & Fataftah, Z. (1977). Tetrahedron, 33, 2127–2129.
  • Manjare, S. T., Singh, H. B. & Butcher, R. J. (2009). Acta Cryst. E65, o2640. [PMC free article] [PubMed]
  • Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED, Oxford Diffraction Ltd, Yarnton, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography