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ISSN: 2056-9890

Oxomemazine hydro­chloride

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and dR. L. Fine Chem, Bangalore 560 064, India
*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 21 June 2011; accepted 28 June 2011; online 2 July 2011)

In the title compound [systematic name: 3-(5,5-dioxo­phen­othia­zin-10-yl)-N,N,2-trimethyl­propanaminium chloride], C18H23N2O2S+·Cl, the dihedral angle between the two outer aromatic rings of the phenothia­zine unit is 30.5 (2)°. In the crystal, the components are linked by N—H⋯Cl and C—H⋯Cl hydrogen bonds and C—H⋯π inter­actions.

Related literature

For background to oxomemazine, see: Amin et al. (2008[Amin, A. S., El-Mossalamy, M. A., Killa, H. M. & Saber, A. L. (2008). Anal. Lett. 41, 80-89.]); El-Didamony, (2005[El-Didamony, A. M. (2005). Arch. Pharm. (Weinheim), 338, 190-197.]). For related structures, see: Harrison et al. (2007[Harrison, W. T. A., Ashok, M. A., Yathirajan, H. S. & Narayana Achar, B. (2007). Acta Cryst. E63, o3277.]); Jasinski et al. (2011[Jasinski, J. P., Pek, A. E., Nayak, P. S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o430-o431.]).

[Scheme 1]

Experimental

Crystal data
  • C18H23N2O2S+·Cl

  • Mr = 366.90

  • Triclinic, [P \overline 1]

  • a = 7.6364 (7) Å

  • b = 10.4177 (9) Å

  • c = 12.4732 (10) Å

  • α = 103.478 (7)°

  • β = 90.624 (7)°

  • γ = 109.852 (8)°

  • V = 903.21 (15) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 3.06 mm−1

  • T = 295 K

  • 0.32 × 0.25 × 0.24 mm

Data collection
  • Oxford Diffraction Xcalibur Ruby Gemini diffractometer

  • Absorption correction: refined from ΔF [XABS2 (Parkin et al., 1995[Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53-56.]) in WinGX (Farrugia (1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.])]Tmin = 0.441, Tmax = 0.528

  • 6466 measured reflections

  • 3598 independent reflections

  • 3120 reflections with I > 2σ(I)

  • Rint = 0.0422

Refinement
  • R[F2 > 2σ(F2)] = 0.079

  • wR(F2) = 0.229

  • S = 1.09

  • 3598 reflections

  • 221 parameters

  • H-atom parameters constrained

  • Δρmax = 0.48 e Å−3

  • Δρmin = −0.55 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2B⋯Cl1 0.91 2.18 3.027 (4) 155
C13—H13A⋯Cl1i 0.97 2.80 3.608 (4) 141
C13—H13B⋯Cl1 0.97 2.76 3.692 (4) 161
C17—H17BCg2ii 0.96 2.62 3.559 (6) 166
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Oxomemazine is an antihistamine and anticholinergic of the phenothiazine chemical class used for the treatment of cough. The extractive spectrophotometric methods for the determination of oxomemazine hydrochloride in bulk and pharmaceutical formulations using some organic dyes is described (El-Didamony, 2005; Amin et al., 2008). The crystal structures of dioxopromethazinium picrate (Harrison et al., 2007) and 1-(10H-phenothiazin-2-yl)ethanone (Jasinski et al., 2011) have been reported. We now report the crystal structure of the title compound, (I).

In the molecule of (I), (Fig. 1), the dihedral angle between the two aromatic rings of the phenothiazine unit is 30.5 (2)°. All bond lengths and angles in (I) are normal. In the crystal structure, N—H···Cl, C—H···Cl hydrogen bonds (Table 1, Fig. 2) and C—H···π interactions help to establish the packing of (I).

Related literature top

For background to oxomemazine, see: Amin et al. (2008); El-Didamony, (2005). For related structures, see: Harrison et al. (2007); Jasinski et al. (2011).

Experimental top

The title compound was obtained as a gift sample from R. L. Fine Chem., Bangalore, India. X-ray quality crystals were obtained from a 1:1 mixture of dimethylformamide and ethanol by slow evaporation (m.p.: 520–523 K).

Refinement top

All H atoms were located geometrically (methyl C—H = 0.98 Å, methylene C—H = 0.99 Å, aromatic C—H = 0.95Å and N—H = 0.91 Å) and refined using a riding model. Their isotropic displacement parameters were set to 1.2 (or 1.5 for the methyl group) times the Ueq of the parent atom. 23 poorly fitted reflections were omitted from the refinement.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of (I) showing displacement ellipsoids for non-H atoms drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of the crystal packing and hydrogen bonding of (I) shown down the a axis.
3-(5,5-dioxophenothiazin-10-yl)-N,N,2-trimethylpropanaminium chloride top
Crystal data top
C18H23N2O2S+·ClZ = 2
Mr = 366.90F(000) = 388
Triclinic, P1Dx = 1.349 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54178 Å
a = 7.6364 (7) ÅCell parameters from 3224 reflections
b = 10.4177 (9) Åθ = 4.7–75.0°
c = 12.4732 (10) ŵ = 3.06 mm1
α = 103.478 (7)°T = 295 K
β = 90.624 (7)°Prism, colourless
γ = 109.852 (8)°0.32 × 0.25 × 0.24 mm
V = 903.21 (15) Å3
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer
3598 independent reflections
Radiation source: Enhance (Cu) X-ray Source3120 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
Detector resolution: 10.5081 pixels mm-1θmax = 75.8°, θmin = 4.7°
ω scansh = 99
Absorption correction: part of the refinement model (ΔF)
[XABS2 (Parkin et al., 1995) in the WinGX (Farrugia (1999).
k = 1212
Tmin = 0.441, Tmax = 0.528l = 015
6466 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)] = 0.079Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.229H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.1168P)2 + 1.2778P]
where P = (Fo2 + 2Fc2)/3
3598 reflections(Δ/σ)max < 0.001
221 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.55 e Å3
Crystal data top
C18H23N2O2S+·Clγ = 109.852 (8)°
Mr = 366.90V = 903.21 (15) Å3
Triclinic, P1Z = 2
a = 7.6364 (7) ÅCu Kα radiation
b = 10.4177 (9) ŵ = 3.06 mm1
c = 12.4732 (10) ÅT = 295 K
α = 103.478 (7)°0.32 × 0.25 × 0.24 mm
β = 90.624 (7)°
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer
3598 independent reflections
Absorption correction: part of the refinement model (ΔF)
[XABS2 (Parkin et al., 1995) in the WinGX (Farrugia (1999).
3120 reflections with I > 2σ(I)
Tmin = 0.441, Tmax = 0.528Rint = 0.074
6466 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0790 restraints
wR(F2) = 0.229H-atom parameters constrained
S = 1.09Δρmax = 0.48 e Å3
3598 reflectionsΔρmin = 0.55 e Å3
221 parameters
Special details top

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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S10.59166 (14)0.20629 (10)0.95014 (7)0.0449 (3)
O10.5426 (5)0.1883 (4)1.0580 (2)0.0663 (10)
O20.7225 (4)0.1441 (3)0.9009 (3)0.0587 (10)
N10.5526 (5)0.3244 (3)0.7585 (3)0.0434 (9)
N20.5857 (5)0.2792 (4)0.3894 (3)0.0448 (10)
C10.4037 (5)0.2045 (4)0.7654 (3)0.0401 (10)
C20.2542 (6)0.1382 (4)0.6801 (3)0.0492 (11)
C30.1031 (6)0.0237 (5)0.6921 (4)0.0552 (14)
C40.0937 (6)0.0284 (5)0.7851 (4)0.0590 (14)
C50.2388 (6)0.0333 (4)0.8684 (4)0.0511 (12)
C60.3941 (5)0.1471 (4)0.8570 (3)0.0412 (10)
C70.6735 (5)0.3847 (4)0.9521 (3)0.0412 (11)
C80.7662 (6)0.4839 (4)1.0502 (3)0.0495 (11)
C90.8514 (6)0.6230 (5)1.0501 (4)0.0547 (12)
C100.8428 (6)0.6621 (4)0.9525 (4)0.0540 (11)
C110.7472 (6)0.5662 (4)0.8560 (4)0.0503 (12)
C120.6580 (5)0.4229 (4)0.8529 (3)0.0400 (10)
C130.5914 (6)0.3516 (4)0.6489 (3)0.0443 (11)
C140.6707 (6)0.2476 (5)0.5775 (3)0.0494 (12)
C150.8375 (9)0.2381 (8)0.6378 (5)0.084 (2)
C160.7363 (6)0.2971 (5)0.4743 (3)0.0507 (14)
C170.4856 (8)0.1292 (5)0.3288 (5)0.0709 (17)
C180.6669 (8)0.3653 (6)0.3094 (4)0.0664 (16)
Cl10.22428 (14)0.32837 (11)0.44260 (9)0.0524 (3)
H2A0.257200.171100.616700.0590*
H2B0.500600.313000.424500.0540*
H3A0.005200.019300.635900.0660*
H4A0.009800.104600.791400.0710*
H5A0.233600.000300.931500.0610*
H8A0.770100.455501.115300.0600*
H9A0.913800.689601.114700.0650*
H10A0.903100.755800.951700.0650*
H11A0.741800.596900.792200.0600*
H13A0.680100.446700.658700.0530*
H13B0.476600.345500.610500.0530*
H14A0.572800.154100.555400.0590*
H15A0.797700.197900.699200.1250*
H15B0.929500.330800.664600.1250*
H15C0.890700.179600.588000.1250*
H16A0.813500.396200.497200.0610*
H16B0.814800.246100.440000.0610*
H17A0.413300.079100.378400.1060*
H17B0.575000.086700.301000.1060*
H17C0.403900.125200.268100.1060*
H18A0.724000.462600.348800.0990*
H18B0.569300.355700.255700.0990*
H18C0.759400.332900.272500.0990*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0587 (6)0.0433 (5)0.0309 (5)0.0145 (4)0.0028 (4)0.0112 (3)
O10.095 (2)0.0633 (19)0.0316 (15)0.0125 (17)0.0023 (15)0.0187 (13)
O20.0562 (17)0.0536 (17)0.069 (2)0.0230 (14)0.0042 (15)0.0155 (15)
N10.0551 (18)0.0425 (16)0.0297 (15)0.0128 (14)0.0014 (13)0.0101 (12)
N20.0564 (18)0.0517 (18)0.0292 (15)0.0247 (15)0.0070 (13)0.0070 (12)
C10.0470 (19)0.0416 (18)0.0321 (17)0.0179 (15)0.0046 (14)0.0063 (14)
C20.058 (2)0.053 (2)0.0380 (19)0.0230 (18)0.0036 (17)0.0090 (16)
C30.048 (2)0.051 (2)0.058 (3)0.0115 (17)0.0092 (18)0.0070 (19)
C40.052 (2)0.050 (2)0.068 (3)0.0080 (18)0.001 (2)0.017 (2)
C50.056 (2)0.047 (2)0.048 (2)0.0138 (17)0.0061 (18)0.0143 (17)
C60.0487 (19)0.0388 (17)0.0350 (18)0.0151 (15)0.0026 (14)0.0075 (14)
C70.052 (2)0.0384 (18)0.0298 (17)0.0134 (15)0.0039 (14)0.0059 (13)
C80.059 (2)0.052 (2)0.0287 (18)0.0134 (18)0.0002 (16)0.0028 (15)
C90.062 (2)0.050 (2)0.041 (2)0.0147 (19)0.0038 (18)0.0018 (17)
C100.062 (2)0.0389 (19)0.052 (2)0.0098 (17)0.0027 (19)0.0066 (17)
C110.062 (2)0.044 (2)0.044 (2)0.0167 (18)0.0038 (17)0.0124 (16)
C120.0455 (18)0.0410 (18)0.0327 (17)0.0156 (15)0.0041 (14)0.0074 (14)
C130.058 (2)0.048 (2)0.0305 (17)0.0195 (17)0.0049 (15)0.0152 (15)
C140.057 (2)0.061 (2)0.040 (2)0.0286 (19)0.0092 (17)0.0195 (18)
C150.082 (3)0.145 (6)0.068 (3)0.072 (4)0.026 (3)0.060 (4)
C160.052 (2)0.071 (3)0.037 (2)0.029 (2)0.0118 (16)0.0172 (18)
C170.080 (3)0.054 (3)0.067 (3)0.022 (2)0.006 (3)0.004 (2)
C180.086 (3)0.084 (3)0.040 (2)0.036 (3)0.020 (2)0.026 (2)
Cl10.0493 (5)0.0565 (6)0.0514 (6)0.0189 (4)0.0047 (4)0.0133 (4)
Geometric parameters (Å, º) top
S1—O11.438 (3)C14—C151.516 (9)
S1—O21.436 (3)C14—C161.524 (6)
S1—C61.733 (4)C2—H2A0.9300
S1—C71.742 (4)C3—H3A0.9300
N1—C11.396 (5)C4—H4A0.9300
N1—C121.394 (5)C5—H5A0.9300
N1—C131.473 (5)C8—H8A0.9300
N2—C161.488 (6)C9—H9A0.9300
N2—C171.491 (7)C10—H10A0.9300
N2—C181.496 (7)C11—H11A0.9300
N2—H2B0.9100C13—H13A0.9700
C1—C61.400 (5)C13—H13B0.9700
C1—C21.417 (6)C14—H14A0.9800
C2—C31.389 (7)C15—H15A0.9600
C3—C41.384 (7)C15—H15B0.9600
C4—C51.379 (7)C15—H15C0.9600
C5—C61.400 (6)C16—H16A0.9700
C7—C81.400 (5)C16—H16B0.9700
C7—C121.401 (5)C17—H17A0.9600
C8—C91.373 (6)C17—H17B0.9600
C9—C101.378 (7)C17—H17C0.9600
C10—C111.380 (7)C18—H18A0.9600
C11—C121.406 (6)C18—H18B0.9600
C13—C141.530 (6)C18—H18C0.9600
O1—S1—O2117.1 (2)C3—C4—H4A120.00
O1—S1—C6111.1 (2)C5—C4—H4A120.00
O1—S1—C7110.2 (2)C4—C5—H5A120.00
O2—S1—C6108.2 (2)C6—C5—H5A120.00
O2—S1—C7108.99 (19)C7—C8—H8A120.00
C6—S1—C799.90 (19)C9—C8—H8A120.00
C1—N1—C12121.7 (3)C8—C9—H9A121.00
C1—N1—C13118.9 (3)C10—C9—H9A121.00
C12—N1—C13119.3 (3)C9—C10—H10A119.00
C16—N2—C17113.2 (4)C11—C10—H10A119.00
C16—N2—C18109.4 (4)C10—C11—H11A119.00
C17—N2—C18110.1 (4)C12—C11—H11A120.00
C16—N2—H2B108.00N1—C13—H13A109.00
C17—N2—H2B108.00N1—C13—H13B109.00
C18—N2—H2B108.00C14—C13—H13A109.00
N1—C1—C2120.7 (3)C14—C13—H13B109.00
N1—C1—C6121.7 (4)H13A—C13—H13B108.00
C2—C1—C6117.6 (4)C13—C14—H14A109.00
C1—C2—C3119.4 (4)C15—C14—H14A109.00
C2—C3—C4122.0 (4)C16—C14—H14A109.00
C3—C4—C5119.6 (5)C14—C15—H15A109.00
C4—C5—C6119.4 (4)C14—C15—H15B109.00
S1—C6—C1118.3 (3)C14—C15—H15C110.00
S1—C6—C5119.3 (3)H15A—C15—H15B109.00
C1—C6—C5122.0 (4)H15A—C15—H15C109.00
C8—C7—C12122.2 (4)H15B—C15—H15C110.00
S1—C7—C8119.0 (3)N2—C16—H16A108.00
S1—C7—C12118.6 (3)N2—C16—H16B108.00
C7—C8—C9119.9 (4)C14—C16—H16A108.00
C8—C9—C10118.8 (4)C14—C16—H16B108.00
C9—C10—C11121.9 (4)H16A—C16—H16B107.00
C10—C11—C12120.9 (4)N2—C17—H17A109.00
N1—C12—C7121.2 (4)N2—C17—H17B110.00
N1—C12—C11122.5 (4)N2—C17—H17C110.00
C7—C12—C11116.2 (4)H17A—C17—H17B109.00
N1—C13—C14112.6 (3)H17A—C17—H17C109.00
C13—C14—C15112.2 (4)H17B—C17—H17C109.00
C13—C14—C16109.1 (4)N2—C18—H18A109.00
C15—C14—C16107.5 (4)N2—C18—H18B109.00
N2—C16—C14115.8 (4)N2—C18—H18C109.00
C1—C2—H2A120.00H18A—C18—H18B109.00
C3—C2—H2A120.00H18A—C18—H18C110.00
C2—C3—H3A119.00H18B—C18—H18C110.00
C4—C3—H3A119.00
O1—S1—C6—C1154.8 (3)C6—C1—C2—C32.2 (6)
O2—S1—C6—C175.4 (4)N1—C1—C2—C3176.5 (4)
C7—S1—C6—C138.5 (4)N1—C1—C6—C5175.2 (4)
O1—S1—C6—C532.5 (4)C2—C1—C6—S1169.0 (3)
O2—S1—C6—C597.4 (4)C2—C1—C6—C53.5 (6)
C7—S1—C6—C5148.7 (3)C1—C2—C3—C40.1 (7)
O1—S1—C7—C830.5 (4)C2—C3—C4—C50.8 (7)
O2—S1—C7—C899.3 (4)C3—C4—C5—C60.5 (7)
C6—S1—C7—C8147.4 (4)C4—C5—C6—C12.7 (7)
O1—S1—C7—C12154.8 (3)C4—C5—C6—S1169.7 (4)
O2—S1—C7—C1275.5 (4)S1—C7—C12—C11172.2 (3)
C6—S1—C7—C1237.8 (4)S1—C7—C12—N110.6 (5)
C12—N1—C13—C14113.2 (4)C12—C7—C8—C92.4 (7)
C13—N1—C1—C222.4 (6)S1—C7—C8—C9172.2 (4)
C12—N1—C1—C624.9 (6)C8—C7—C12—C112.4 (6)
C12—N1—C1—C2153.8 (4)C8—C7—C12—N1174.9 (4)
C1—N1—C13—C1470.6 (5)C7—C8—C9—C100.3 (7)
C13—N1—C12—C7158.2 (4)C8—C9—C10—C111.7 (7)
C13—N1—C1—C6159.0 (4)C9—C10—C11—C121.6 (7)
C1—N1—C12—C725.7 (6)C10—C11—C12—C70.4 (6)
C1—N1—C12—C11151.4 (4)C10—C11—C12—N1176.8 (4)
C13—N1—C12—C1124.8 (6)N1—C13—C14—C1551.8 (6)
C18—N2—C16—C14165.0 (4)N1—C13—C14—C16170.8 (4)
C17—N2—C16—C1471.7 (5)C15—C14—C16—N2165.3 (4)
N1—C1—C6—S112.3 (5)C13—C14—C16—N272.9 (5)
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C1–C6 benzene ring.
D—H···AD—HH···AD···AD—H···A
N2—H2B···Cl10.912.183.027 (4)155
C13—H13A···Cl1i0.972.803.608 (4)141
C13—H13B···Cl10.972.763.692 (4)161
C17—H17B···Cg2ii0.962.623.559 (6)166
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC18H23N2O2S+·Cl
Mr366.90
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)7.6364 (7), 10.4177 (9), 12.4732 (10)
α, β, γ (°)103.478 (7), 90.624 (7), 109.852 (8)
V3)903.21 (15)
Z2
Radiation typeCu Kα
µ (mm1)3.06
Crystal size (mm)0.32 × 0.25 × 0.24
Data collection
DiffractometerOxford Diffraction Xcalibur Ruby Gemini
diffractometer
Absorption correctionPart of the refinement model (ΔF)
[XABS2 (Parkin et al., 1995) in the WinGX (Farrugia (1999).
Tmin, Tmax0.441, 0.528
No. of measured, independent and
observed [I > 2σ(I)] reflections
6466, 3598, 3120
Rint0.074
(sin θ/λ)max1)0.629
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.079, 0.229, 1.09
No. of reflections3598
No. of parameters221
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.48, 0.55

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C1–C6 benzene ring.
D—H···AD—HH···AD···AD—H···A
N2—H2B···Cl10.912.183.027 (4)155
C13—H13A···Cl1i0.972.803.608 (4)141
C13—H13B···Cl10.972.763.692 (4)161
C17—H17B···Cg2ii0.962.623.559 (6)166
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z+1.
 

Acknowledgements

MSS thanks the University of Mysore for research facilities and R. L. Fine Chem., Bangalore, India, for the gift sample. RJB acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

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