Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2647
https://doi.org/10.1107/S1600536811036932

3-(4-Bromo­anilino)-3-(4-chloro­phen­yl)-1-phenyl­propan-1-one

Mehrdad Pourayoubi,a* Zohreh Shobeiri,a Giuseppe Brunob and Hadi Amiri Rudbarib

aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran, and bDipartimento di Chimica Inorganica, Vill. S. Agata, Salita Sperone 31, Università di Messina, 98166 Messina, Italy
*Correspondence e-mail: mehrdad_pourayoubi@yahoo.com

(Received 24 August 2011; accepted 12 September 2011; online 17 September 2011)

The asymmetric C atom in the title compound, C21H17BrClNO, is in a slightly distorted tetra­hedral environment and the NH unit adopts a gauche orientation with respect to the CO group. In the crystal, pairs of inter­molecular N—H⋯O hydrogen bonds form centrosymmetric dimers.

Related literature

For background to β-amino ketones, see: Scettri et al. (2008[Scettri, A., Massa, A., Palombi, L., Villano, R. & Acocella, M. R. (2008). Tetrahedron Asymmetry, 19, 2149-2152.]). For related structures, see: Shobeiri et al. (2011[Shobeiri, Z., Pourayoubi, M., Heydari, A., Percino, T. M. & Leyva Ramírez, M. A. (2011). C. R. Chim. 14, 597-603.]); Zhang et al. (2008[Zhang, L.-P., Wei, L.-J., Chen, M.-Q. & Zhang, Z.-H. (2008). Acta Cryst. E64, o1327.]). For hydrogen-bond motifs and their graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C21H17BrClNO

  • Mr = 414.72

  • Monoclinic, P 21 /n

  • a = 10.6571 (4) Å

  • b = 17.2432 (6) Å

  • c = 10.8602 (4) Å

  • β = 113.571 (2)°

  • V = 1829.19 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.40 mm−1

  • T = 296 K

  • 0.35 × 0.31 × 0.11 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.589, Tmax = 0.746

  • 69312 measured reflections

  • 3983 independent reflections

  • 3274 reflections with I > 2σ(I)

  • Rint = 0.036
Refinement

  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.084

  • S = 1.03

  • 3983 reflections

  • 230 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.71 e Å−3

  • Δρmin = −0.86 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H⋯O1i 0.81 (3) 2.23 (3) 2.992 (3) 156 (2)
Symmetry code: (i) -x, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811036932/qm2027sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811036932/qm2027Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811036932/qm2027Isup3.cml

checkCIF report


Comment top

β-Amino ketones, of the formula [R1]CH[NHR2][CH2C(O)R3], such as the title compound have attracted attention because of their roles as important intermediates for the synthesis of natural products and chiral auxiliaries (Scettri et al., 2008). In the previous work, the structure determination of 3-(4-bromophenylamino)-1-phenyl-3-p-tolylpropan-1-one (Shobeiri et al., 2011) has been investigated. Here, we report the synthesis and crystal structure of the title molecule, [4-Cl—C6H4]CH[NHC6H4-4-Br][CH2C(O)C6H5]. The asymmetric C atom has a slightly distorted tetrahedral configuration (Fig 1) with the bond angles in the range of 107.92 (16)° [N(1)—C(9)—C(8)] to 114.69 (16)° [N(1)—C(9)—C(10)]. In the crystal, pairs of intermolecular N—H···O(C) hydrogen bonds (Table 1) form centrosymmetric dimers as R22(12) rings (for graph-set notation, see Bernstein et al., 1995). A view of crystal packing is shown in Fig. 2.

Related literature top

For background to β-amino ketones, see: Scettri et al. (2008). For related structures, see: Shobeiri et al. (2011); Zhang et al. (2008). For hydrogen-bond motifs and their graph-set notation, see: Bernstein et al. (1995).

Experimental top

To a magnetically stirred mixture of 3-(4-chlorophenyl)-1-phenylprop-2-en-1-one (0.24 g, 1.0 mmol) and Ag3PW12O40 (0.32 g, 0.10 mmol) as catalyst, in ethanol (5 ml), 4-bromoaniline (0.20 g, 1.2 mmol) was added at room temperature. The reaction completion was monitored by thin layer chromatography (TLC). The catalyst Ag3PW12O40 was collected by centrifugation. The reaction mixture was extracted with distilled water and ether (2×10 ml). The combined organic layer was evaporated to obtain crude product which was washed with hexane to give pure product. Single crystals of the product were obtained from a solution of CHCl3/CH3OH at room temperature.

Refinement top

H atoms of N—H was found in a difference Fourier map and refined isotropically with a distance restraint of N1—H = 0.81 (3) Å. The other H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93(aromatic CH), 0.97(CH2) and 0.98 (aliphatic CH) Å and with Uiso(H) = 1.2 and 1.5 Ueq(C).

Structure description top

β-Amino ketones, of the formula [R1]CH[NHR2][CH2C(O)R3], such as the title compound have attracted attention because of their roles as important intermediates for the synthesis of natural products and chiral auxiliaries (Scettri et al., 2008). In the previous work, the structure determination of 3-(4-bromophenylamino)-1-phenyl-3-p-tolylpropan-1-one (Shobeiri et al., 2011) has been investigated. Here, we report the synthesis and crystal structure of the title molecule, [4-Cl—C6H4]CH[NHC6H4-4-Br][CH2C(O)C6H5]. The asymmetric C atom has a slightly distorted tetrahedral configuration (Fig 1) with the bond angles in the range of 107.92 (16)° [N(1)—C(9)—C(8)] to 114.69 (16)° [N(1)—C(9)—C(10)]. In the crystal, pairs of intermolecular N—H···O(C) hydrogen bonds (Table 1) form centrosymmetric dimers as R22(12) rings (for graph-set notation, see Bernstein et al., 1995). A view of crystal packing is shown in Fig. 2.

For background to β-amino ketones, see: Scettri et al. (2008). For related structures, see: Shobeiri et al. (2011); Zhang et al. (2008). For hydrogen-bond motifs and their graph-set notation, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. An ORTEP-style plot of title compound with labeling. Ellipsoids are given at the 50% probability level.
[Figure 2] Fig. 2. Part of the crystal packing of the title compound showing a centrosymmetric H-bonded (dashed lines) dimer. Only H atoms involving in hydrogen bonds are shown.
3-(4-Bromoanilino)-3-(4-chlorophenyl)-1-phenylpropan-1-one top
Crystal data top
C21H17BrClNOF(000) = 840
Mr = 414.72Dx = 1.506 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9986 reflections
a = 10.6571 (4) Åθ = 2.4–23.8°
b = 17.2432 (6) ŵ = 2.40 mm−1
c = 10.8602 (4) ÅT = 296 K
β = 113.571 (2)°Irregular, colorless
V = 1829.19 (12) Å30.35 × 0.31 × 0.11 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer		3983 independent reflections
Radiation source: fine-focus sealed tube3274 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
φ and ω scansθmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −13→13
Tmin = 0.589, Tmax = 0.746k = −22→22
69312 measured reflectionsl = −13→13
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0314P)2 + 1.4336P]
where P = (Fo2 + 2Fc2)/3
3983 reflections(Δ/σ)max = 0.001
230 parametersΔρmax = 0.71 e Å−3
0 restraintsΔρmin = −0.86 e Å−3
Crystal data top
C21H17BrClNOV = 1829.19 (12) Å3
Mr = 414.72Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.6571 (4) ŵ = 2.40 mm−1
b = 17.2432 (6) ÅT = 296 K
c = 10.8602 (4) Å0.35 × 0.31 × 0.11 mm
β = 113.571 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		3983 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		3274 reflections with I > 2σ(I)
Tmin = 0.589, Tmax = 0.746Rint = 0.036
69312 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.71 e Å−3
3983 reflectionsΔρmin = −0.86 e Å−3
230 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Br−0.04722 (3)0.80334 (2)−0.19048 (3)0.06568 (12)
Cl−0.16806 (9)0.56173 (4)0.49694 (7)0.0721 (2)
O10.17572 (18)1.03398 (10)0.6206 (2)0.0634 (5)
N10.08682 (19)0.90054 (10)0.38597 (18)0.0371 (4)
C18−0.0066 (2)0.83266 (15)−0.0093 (2)0.0450 (5)
C170.0762 (3)0.78643 (15)0.0933 (2)0.0494 (6)
H170.11180.74090.07430.059*
C160.1072 (2)0.80736 (13)0.2259 (2)0.0450 (5)
H160.16350.77570.29530.054*
C210.0549 (2)0.87508 (12)0.2558 (2)0.0351 (4)
C90.1518 (2)0.85036 (11)0.5014 (2)0.0341 (4)
H90.24170.83510.50490.041*
C80.1731 (2)0.89759 (12)0.6286 (2)0.0385 (5)
H8A0.08480.90640.63230.046*
H8B0.22810.86730.70690.046*
C70.2419 (2)0.97478 (12)0.6350 (2)0.0389 (5)
C60.3887 (2)0.97840 (12)0.65830 (19)0.0358 (4)
C50.4741 (2)0.91441 (13)0.6986 (2)0.0405 (5)
H50.44000.86720.71320.049*
C40.6101 (2)0.92042 (15)0.7171 (2)0.0498 (6)
H40.66730.87740.74500.060*
C30.6605 (2)0.98986 (17)0.6944 (3)0.0556 (6)
H30.75140.99340.70530.067*
C20−0.0291 (2)0.92111 (13)0.1491 (2)0.0437 (5)
H20−0.06540.96670.16700.052*
C19−0.0594 (2)0.90066 (15)0.0179 (2)0.0486 (5)
H19−0.11490.9323−0.05200.058*
C100.0717 (2)0.77732 (11)0.5009 (2)0.0336 (4)
C110.1383 (2)0.70874 (13)0.5539 (2)0.0455 (5)
H110.23350.70720.58880.055*
C120.0668 (3)0.64243 (14)0.5562 (3)0.0538 (6)
H120.11290.59670.59260.065*
C13−0.0743 (3)0.64527 (13)0.5035 (2)0.0460 (5)
C14−0.1434 (2)0.71292 (14)0.4522 (2)0.0460 (5)
H14−0.23850.71440.41880.055*
C15−0.0702 (2)0.77871 (12)0.4507 (2)0.0409 (5)
H15−0.11660.82460.41560.049*
C20.5775 (3)1.05403 (16)0.6559 (3)0.0565 (6)
H20.61251.10100.64170.068*
C10.4420 (2)1.04882 (13)0.6382 (2)0.0463 (5)
H10.38621.09240.61290.056*
H0.031 (3)0.9290 (15)0.396 (3)0.046 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.04927 (16)0.1060 (3)0.03996 (14)−0.00352 (14)0.01597 (11)−0.00835 (13)
Cl0.0956 (5)0.0517 (4)0.0638 (4)−0.0335 (4)0.0266 (4)0.0014 (3)
O10.0462 (10)0.0427 (9)0.0988 (15)0.0070 (8)0.0262 (10)−0.0028 (9)
N10.0382 (9)0.0331 (9)0.0392 (9)0.0026 (8)0.0145 (8)0.0021 (7)
C180.0366 (11)0.0616 (14)0.0372 (11)−0.0081 (10)0.0153 (9)−0.0005 (10)
C170.0552 (14)0.0516 (13)0.0476 (13)0.0056 (11)0.0271 (11)−0.0006 (11)
C160.0483 (12)0.0469 (13)0.0403 (11)0.0105 (10)0.0183 (10)0.0080 (10)
C210.0319 (10)0.0349 (10)0.0376 (10)−0.0048 (8)0.0129 (8)0.0024 (8)
C90.0296 (9)0.0346 (10)0.0368 (10)0.0004 (8)0.0117 (8)0.0005 (8)
C80.0347 (10)0.0433 (11)0.0375 (11)−0.0052 (9)0.0144 (9)−0.0027 (9)
C70.0371 (11)0.0393 (11)0.0370 (10)−0.0010 (9)0.0114 (9)−0.0042 (9)
C60.0348 (10)0.0375 (11)0.0324 (10)−0.0048 (8)0.0106 (8)−0.0037 (8)
C50.0361 (10)0.0406 (11)0.0395 (11)−0.0032 (9)0.0094 (9)0.0001 (9)
C40.0366 (11)0.0565 (14)0.0495 (13)0.0017 (10)0.0100 (10)−0.0039 (11)
C30.0380 (12)0.0771 (18)0.0495 (14)−0.0132 (12)0.0151 (10)−0.0062 (13)
C200.0407 (11)0.0390 (11)0.0453 (12)0.0026 (9)0.0107 (10)0.0040 (9)
C190.0398 (11)0.0565 (14)0.0406 (12)0.0000 (10)0.0068 (9)0.0100 (10)
C100.0356 (10)0.0316 (10)0.0327 (9)−0.0010 (8)0.0127 (8)−0.0009 (8)
C110.0405 (12)0.0405 (12)0.0484 (13)0.0045 (9)0.0104 (10)0.0056 (10)
C120.0652 (16)0.0361 (12)0.0516 (14)0.0019 (11)0.0143 (12)0.0081 (10)
C130.0624 (15)0.0373 (12)0.0386 (11)−0.0157 (10)0.0206 (11)−0.0041 (9)
C140.0410 (12)0.0478 (13)0.0486 (13)−0.0085 (10)0.0173 (10)−0.0052 (10)
C150.0363 (11)0.0341 (10)0.0493 (12)0.0005 (8)0.0141 (9)0.0003 (9)
C20.0559 (15)0.0589 (16)0.0519 (14)−0.0240 (13)0.0186 (12)0.0009 (12)
C10.0491 (13)0.0408 (12)0.0441 (12)−0.0060 (10)0.0134 (10)0.0007 (10)
Geometric parameters (Å, º) top
Br—C181.906 (2)C5—C41.385 (3)
Cl—C131.738 (2)C5—H50.9300
O1—C71.215 (3)C4—C31.374 (4)
N1—C211.386 (3)C4—H40.9300
N1—C91.451 (3)C3—C21.374 (4)
N1—H0.81 (3)C3—H30.9300
C18—C171.367 (3)C20—C191.375 (3)
C18—C191.382 (4)C20—H200.9300
C17—C161.391 (3)C19—H190.9300
C17—H170.9300C10—C111.381 (3)
C16—C211.387 (3)C10—C151.388 (3)
C16—H160.9300C11—C121.380 (3)
C21—C201.395 (3)C11—H110.9300
C9—C101.520 (3)C12—C131.379 (4)
C9—C81.540 (3)C12—H120.9300
C9—H90.9800C13—C141.373 (3)
C8—C71.507 (3)C14—C151.381 (3)
C8—H8A0.9700C14—H140.9300
C8—H8B0.9700C15—H150.9300
C7—C61.483 (3)C2—C11.381 (4)
C6—C51.385 (3)C2—H20.9300
C6—C11.394 (3)C1—H10.9300
C21—N1—C9121.99 (17)C3—C4—C5120.0 (2)
C21—N1—H115.5 (18)C3—C4—H4120.0
C9—N1—H111.7 (18)C5—C4—H4120.0
C17—C18—C19120.4 (2)C2—C3—C4120.4 (2)
C17—C18—Br119.53 (19)C2—C3—H3119.8
C19—C18—Br120.11 (17)C4—C3—H3119.8
C18—C17—C16120.1 (2)C19—C20—C21121.5 (2)
C18—C17—H17119.9C19—C20—H20119.3
C16—C17—H17119.9C21—C20—H20119.3
C21—C16—C17120.6 (2)C20—C19—C18119.5 (2)
C21—C16—H16119.7C20—C19—H19120.3
C17—C16—H16119.7C18—C19—H19120.3
N1—C21—C16123.20 (19)C11—C10—C15118.5 (2)
N1—C21—C20118.79 (19)C11—C10—C9120.90 (19)
C16—C21—C20117.9 (2)C15—C10—C9120.61 (18)
N1—C9—C10114.69 (16)C12—C11—C10121.4 (2)
N1—C9—C8107.92 (16)C12—C11—H11119.3
C10—C9—C8108.81 (16)C10—C11—H11119.3
N1—C9—H9108.4C13—C12—C11118.8 (2)
C10—C9—H9108.4C13—C12—H12120.6
C8—C9—H9108.4C11—C12—H12120.6
C7—C8—C9113.74 (17)C14—C13—C12121.2 (2)
C7—C8—H8A108.8C14—C13—Cl118.75 (19)
C9—C8—H8A108.8C12—C13—Cl120.06 (19)
C7—C8—H8B108.8C13—C14—C15119.3 (2)
C9—C8—H8B108.8C13—C14—H14120.4
H8A—C8—H8B107.7C15—C14—H14120.4
O1—C7—C6120.3 (2)C14—C15—C10120.9 (2)
O1—C7—C8119.32 (19)C14—C15—H15119.6
C6—C7—C8120.35 (18)C10—C15—H15119.6
C5—C6—C1119.1 (2)C3—C2—C1120.0 (2)
C5—C6—C7122.37 (19)C3—C2—H2120.0
C1—C6—C7118.56 (19)C1—C2—H2120.0
C4—C5—C6120.2 (2)C2—C1—C6120.2 (2)
C4—C5—H5119.9C2—C1—H1119.9
C6—C5—H5119.9C6—C1—H1119.9
C19—C18—C17—C160.4 (4)C16—C21—C20—C19−0.2 (3)
Br—C18—C17—C16179.65 (18)C21—C20—C19—C180.6 (3)
C18—C17—C16—C210.0 (4)C17—C18—C19—C20−0.7 (4)
C9—N1—C21—C16−14.4 (3)Br—C18—C19—C20−179.93 (17)
C9—N1—C21—C20168.47 (19)N1—C9—C10—C11145.8 (2)
C17—C16—C21—N1−177.2 (2)C8—C9—C10—C11−93.3 (2)
C17—C16—C21—C20−0.1 (3)N1—C9—C10—C15−36.2 (3)
C21—N1—C9—C10−59.1 (2)C8—C9—C10—C1584.8 (2)
C21—N1—C9—C8179.46 (17)C15—C10—C11—C120.8 (3)
N1—C9—C8—C7−50.4 (2)C9—C10—C11—C12178.8 (2)
C10—C9—C8—C7−175.40 (17)C10—C11—C12—C130.3 (4)
C9—C8—C7—O1109.1 (2)C11—C12—C13—C14−1.5 (4)
C9—C8—C7—C6−70.7 (2)C11—C12—C13—Cl176.77 (19)
O1—C7—C6—C5168.4 (2)C12—C13—C14—C151.5 (4)
C8—C7—C6—C5−11.8 (3)Cl—C13—C14—C15−176.77 (18)
O1—C7—C6—C1−11.9 (3)C13—C14—C15—C10−0.4 (3)
C8—C7—C6—C1167.93 (19)C11—C10—C15—C14−0.7 (3)
C1—C6—C5—C4−0.7 (3)C9—C10—C15—C14−178.8 (2)
C7—C6—C5—C4179.0 (2)C4—C3—C2—C1−0.7 (4)
C6—C5—C4—C3−0.6 (4)C3—C2—C1—C6−0.5 (4)
C5—C4—C3—C21.3 (4)C5—C6—C1—C21.2 (3)
N1—C21—C20—C19177.1 (2)C7—C6—C1—C2−178.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H···O1i0.81 (3)2.23 (3)2.992 (3)156 (2)
Symmetry code: (i) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formulaC21H17BrClNO
Mr414.72
Crystal system, space groupMonoclinic, P21/n
Temperature (K)296
a, b, c (Å)10.6571 (4), 17.2432 (6), 10.8602 (4)
β (°) 113.571 (2)
V (Å3)1829.19 (12)
Z4
Radiation typeMo Kα
µ (mm−1)2.40
Crystal size (mm)0.35 × 0.31 × 0.11
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.589, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections		69312, 3983, 3274
Rint0.036
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.084, 1.03
No. of reflections3983
No. of parameters230
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.71, −0.86

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H···O1i0.81 (3)2.23 (3)2.992 (3)156 (2)
Symmetry code: (i) −x, −y+2, −z+1.
 

Acknowledgements

Support of this investigation by Ferdowsi University of Mashhad is gratefully acknowledged.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
 First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationScettri, A., Massa, A., Palombi, L., Villano, R. & Acocella, M. R. (2008). Tetrahedron Asymmetry, 19, 2149–2152.  Web of Science CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationShobeiri, Z., Pourayoubi, M., Heydari, A., Percino, T. M. & Leyva Ramírez, M. A. (2011). C. R. Chim. 14, 597–603.  Web of Science CSD CrossRef CAS Google Scholar
 First citationZhang, L.-P., Wei, L.-J., Chen, M.-Q. & Zhang, Z.-H. (2008). Acta Cryst. E64, o1327.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2647
https://doi.org/10.1107/S1600536811036932
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS