N-[(2-Chloro-3-quinol­yl)meth­yl]-4-fluoro­aniline

Jasinski, J.P.; Pek, A.E.; Chidan Kumar, C.S.; Yathirajan, H.S.; Kumar, S.

doi:10.1107/S1600536810036056

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages o2548-o2549

doi:10.1107/S1600536810036056

Open

access

N-[(2-Chloro-3-quinolyl)methyl]-4-fluoroaniline

Jerry P. Jasinski,^a ^* Albert E. Pek,^a C. S. Chidan Kumar,^b H. S. Yathirajan ^b and Suresh Kumar ^c

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Hamdard University, Jamia Hamdard, New Delhi 110 062, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 14 August 2010; accepted 7 September 2010; online 11 September 2010)

In the title compound, C₁₆H₁₂ClFN₂, the dihedral angle between the quinoline ring system and the flourophenyl ring is 86.70 (4)°. In the crystal, molecules are linked into chains along the a axis by N—H⋯N hydrogen bonds. In addition, C—H⋯π interactions involving the two benzene rings are observed.

Related literature

For general background, properties and the biological activity of quinolines, see: Campbell et al. (1988 ); Dutta et al. (2002 ); Markees et al. (1970 ); Meth-Cohn et al. (1981 ); Michael et al. (1997 ); Morimoto et al. (1991 ); Padwa et al. (1999 ); Rajendran & Karavembu (2002 ); Robert & Meunier et al. (1998 ). For the synthesis of quinolines, see: Kouznetsov et al. (2005 ). For related structures, see: Butcher et al. 2007 ); Lynch et al. (2001 ); Subashini et al. (2009 ); Yathirajan et al. (2007 ); Wu et al. (2009 ); Khan et al. (2010 ). For bond-length data, see: Allen et al. (1987 ) .

Experimental

Crystal data

C₁₆H₁₂ClFN₂
M_r = 286.73
Triclinic, $[P \overline 1]$
a = 7.3661 (8) Å
b = 8.8967 (9) Å
c = 11.5129 (12) Å
α = 68.704 (1)°
β = 74.468 (1)°
γ = 75.445 (1)°
V = 667.25 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 100 K
0.55 × 0.50 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.858, T_max = 0.932
8162 measured reflections
3930 independent reflections
3633 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.094
S = 1.03
3930 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C11–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H18⋯N1ⁱ	0.86	2.30	3.1353 (12)	165
C4—H4⋯Cg2ⁱⁱ	0.93	2.91	3.7494 (13)	151
C10—H10A⋯Cg1ⁱⁱⁱ	0.97	2.62	3.5365 (12)	157
C10—H10B⋯Cg2^iv	0.97	2.98	3.8083 (11)	145
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y+1, -z+1; (iii) -x+2, -y, -z+1; (iv) -x+1, -y, -z+2.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036056/ci5158sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810036056/ci5158Isup2.hkl

checkCIF report

Comment top

Quinoline derivatives represent a major class of heterocycles, and a number of preparations using them have been known since the late 1800s. Quinolines are found in natural products (Morimoto et al., 1991; Michael et al., 1997), numerous commercial products, including fragrances, dyes (Padwa et al., 1999) and biologically active compounds (Markees et al., 1970; Campbell et al., 1988). Quinoline alkaloids such as quinine, chloroquin, mefloquine and amodiaquine are used as efficient drugs for the treatment of malaria (Robert & Meunier, 1998). Several quinoline derivatives have been evaluated in vitro against a number of parasites of HTLV-1 transformed cells. 2-Chloro substituted quinolines are vital synthetic intermediates in the construction of a large number of linearly fused tri- and tetra- cyclic quinolines studied for the DNA intercalating properties (Meth-Cohn et al., 1981; Rajendran & Karavembu, 2002; Dutta et al., 2002). A review on recent progress in the synthesis of quinolines (Kouznetsov et al. 2005) has been described. The crystal structure studies of 8-chloro-2-methylquinoline (Wu et al., 2009), 2-chloro-4-methylquinoline (Lynch et al., 2001), 4-chloro-8-(trifluoromethyl)quinoline (Yathirajan et al., 2007), 1-(quinolin-2-yl)ethanone (Butcher et al., 2007) and 2-chloro-7-methylquinoline-3-carbaldehyde (Subashini et al., 2009) have been reported. In view of the importance of quinolines, the paper reports the synthesis and crystal structure of the title compound.

In the title molecule (Fig. 1), the 2-chloroquinoline ring system and 4-fluoroaniline ring are bonded to a methane carbon, C10. The dihedral angle between the mean planes of the planar chloroquinoline ring system (dihedral angle between rings = 0.92 (5)°) and the flourophenyl ring is 86.70 (4)°. Bond distances (Allen et al., 1987) and angles are in normal ranges.

The molecules are linked into chains along the a axis by N—H···N hydrogen bonds (Fig. 2). In addition, C—H···π interactions involving the two benzene rings (Table 1) influence crystal packing in the unit cell.

Related literature top

For general background, properties and the biological activity of quinolines, see: Campbell et al. (1988); Dutta et al. (2002); Markees et al. (1970); Meth-Cohn et al. (1981); Michael et al. (1997); Morimoto et al. (1991); Padwa et al. (1999); Rajendran & Karavembu (2002); Robert & Meunier et al. (1998). For the synthesis of quinolines, see: Kouznetsov et al. (2005). For related structures, see: Butcher et al. 2007); Lynch et al. (2001); Subashini et al. (2009); Yathirajan et al. (2007); Wu et al. (2009); Khan et al. (2010). For bond-length data, see: Allen et al. (1987 ).

Experimental top

In a mixture of 3-(chloromethyl)-2-chloroquinoline (0.003 mol) and substituted phenyl amine (0.003 mol) in 20 ml of absolute ethanol, 1 ml of triethylamine (TEA) was added and refluxed for 12–15 hrs (Fig. 3). After completion of the reaction, content of the flask was reduced to half and left overnight. The crystalline mass obtained was filtered off, washed with water, dried and re-crystallized from ethanol to give N-[(2-chloroquinolin-3-yl)methyl]-4-fluoroaniline. X-ray quality crystals were obtained by slow evaporation of a methanol solution (m.p. 413–415 K).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom-labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound, viewed down the b axis. Dashed lines indicate weak N—H···N hydrogen bonds.
	Fig. 3. Reaction scheme for the title compound.

N-[(2-Chloro-3-quinolyl)methyl]-4-fluoroaniline top

Crystal data top

C₁₆H₁₂ClFN₂	Z = 2
M_r = 286.73	F(000) = 296
Triclinic, P1	D_x = 1.427 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3661 (8) Å	Cell parameters from 5222 reflections
b = 8.8967 (9) Å	θ = 2.5–31.0°
c = 11.5129 (12) Å	µ = 0.29 mm⁻¹
α = 68.704 (1)°	T = 100 K
β = 74.468 (1)°	Plate, colourless
γ = 75.445 (1)°	0.55 × 0.50 × 0.25 mm
V = 667.25 (12) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	3930 independent reflections
Radiation source: fine-focus sealed tube	3633 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
ω scans	θ_max = 31.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
T_min = 0.858, T_max = 0.932	k = −12→12
8162 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0533P)² + 0.2404P] where P = (F_o² + 2F_c²)/3
3930 reflections	(Δ/σ)_max = 0.001
181 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₆H₁₂ClFN₂	γ = 75.445 (1)°
M_r = 286.73	V = 667.25 (12) Å³
Triclinic, P1	Z = 2
a = 7.3661 (8) Å	Mo Kα radiation
b = 8.8967 (9) Å	µ = 0.29 mm⁻¹
c = 11.5129 (12) Å	T = 100 K
α = 68.704 (1)°	0.55 × 0.50 × 0.25 mm
β = 74.468 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3930 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3633 reflections with I > 2σ(I)
T_min = 0.858, T_max = 0.932	R_int = 0.014
8162 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.03	Δρ_max = 0.49 e Å⁻³
3930 reflections	Δρ_min = −0.30 e Å⁻³
181 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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

	x	y	z	U_iso*/U_eq
Cl1	1.15120 (4)	−0.21591 (3)	0.79554 (2)	0.02245 (8)
N1	1.24567 (12)	0.03932 (10)	0.60973 (8)	0.01634 (16)
N2	0.55793 (12)	0.03799 (11)	0.74940 (8)	0.01744 (17)
H18	0.4905	0.0291	0.7025	0.021*
F1	0.24347 (10)	0.46529 (9)	1.02706 (7)	0.02663 (16)
C7	1.09918 (14)	−0.03020 (11)	0.67819 (9)	0.01494 (17)
C1	1.02460 (14)	0.25805 (11)	0.49326 (9)	0.01455 (17)
C10	0.74539 (14)	−0.05999 (12)	0.75411 (9)	0.01625 (18)
H10A	0.7513	−0.1557	0.7308	0.020*
H10B	0.7657	−0.0977	0.8407	0.020*
C8	0.90473 (13)	0.03112 (11)	0.66692 (9)	0.01406 (17)
C5	1.36831 (15)	0.26375 (13)	0.44050 (10)	0.01949 (19)
H5	1.4913	0.2165	0.4552	0.023*
C6	1.21153 (14)	0.18553 (12)	0.51570 (9)	0.01520 (17)
C9	0.87191 (13)	0.17731 (12)	0.57294 (9)	0.01522 (17)
H9	0.7474	0.2240	0.5615	0.018*
C14	0.21346 (15)	0.33659 (13)	0.88812 (10)	0.0206 (2)
H14	0.0879	0.3910	0.8882	0.025*
C11	0.48346 (14)	0.14581 (12)	0.81816 (9)	0.01552 (18)
C2	0.99836 (15)	0.40819 (12)	0.39406 (9)	0.01792 (19)
H17	0.8764	0.4568	0.3777	0.022*
C13	0.32377 (16)	0.36116 (12)	0.95720 (10)	0.01941 (19)
C3	1.15214 (16)	0.48201 (13)	0.32212 (10)	0.01972 (19)
H3	1.1338	0.5806	0.2572	0.024*
C12	0.59034 (14)	0.17592 (12)	0.88891 (9)	0.01760 (18)
H12	0.7166	0.1235	0.8889	0.021*
C4	1.33828 (16)	0.40979 (13)	0.34565 (10)	0.0210 (2)
H4	1.4413	0.4616	0.2965	0.025*
C15	0.29365 (14)	0.22899 (13)	0.81854 (10)	0.01916 (19)
H15	0.2208	0.2116	0.7714	0.023*
C16	0.50987 (15)	0.28339 (13)	0.95926 (10)	0.01933 (19)
H16	0.5809	0.3021	1.0068	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01931 (13)	0.01748 (12)	0.02433 (13)	−0.00220 (9)	−0.00775 (9)	0.00240 (9)
N1	0.0150 (4)	0.0161 (4)	0.0176 (4)	−0.0027 (3)	−0.0047 (3)	−0.0039 (3)
N2	0.0128 (4)	0.0214 (4)	0.0208 (4)	−0.0023 (3)	−0.0036 (3)	−0.0099 (3)
F1	0.0308 (4)	0.0241 (3)	0.0268 (3)	−0.0030 (3)	−0.0011 (3)	−0.0146 (3)
C7	0.0154 (4)	0.0129 (4)	0.0162 (4)	−0.0015 (3)	−0.0049 (3)	−0.0037 (3)
C1	0.0149 (4)	0.0143 (4)	0.0149 (4)	−0.0024 (3)	−0.0030 (3)	−0.0052 (3)
C10	0.0139 (4)	0.0152 (4)	0.0183 (4)	−0.0028 (3)	−0.0019 (3)	−0.0045 (3)
C8	0.0137 (4)	0.0142 (4)	0.0148 (4)	−0.0028 (3)	−0.0028 (3)	−0.0049 (3)
C5	0.0159 (4)	0.0216 (5)	0.0208 (5)	−0.0063 (4)	−0.0028 (3)	−0.0050 (4)
C6	0.0147 (4)	0.0157 (4)	0.0161 (4)	−0.0033 (3)	−0.0033 (3)	−0.0054 (3)
C9	0.0134 (4)	0.0156 (4)	0.0164 (4)	−0.0016 (3)	−0.0037 (3)	−0.0049 (3)
C14	0.0181 (4)	0.0211 (5)	0.0200 (5)	−0.0001 (4)	−0.0030 (4)	−0.0063 (4)
C11	0.0152 (4)	0.0152 (4)	0.0143 (4)	−0.0044 (3)	−0.0012 (3)	−0.0025 (3)
C2	0.0197 (4)	0.0159 (4)	0.0169 (4)	−0.0022 (3)	−0.0044 (3)	−0.0035 (3)
C13	0.0242 (5)	0.0161 (4)	0.0165 (4)	−0.0047 (4)	−0.0001 (4)	−0.0054 (3)
C3	0.0239 (5)	0.0166 (4)	0.0174 (4)	−0.0054 (4)	−0.0037 (4)	−0.0029 (3)
C12	0.0165 (4)	0.0180 (4)	0.0180 (4)	−0.0051 (3)	−0.0030 (3)	−0.0043 (3)
C4	0.0210 (5)	0.0212 (5)	0.0202 (5)	−0.0088 (4)	−0.0012 (4)	−0.0043 (4)
C15	0.0165 (4)	0.0220 (5)	0.0196 (4)	−0.0016 (4)	−0.0051 (3)	−0.0073 (4)
C16	0.0221 (5)	0.0199 (4)	0.0175 (4)	−0.0077 (4)	−0.0037 (4)	−0.0050 (4)

Geometric parameters (Å, º) top

Cl1—C7	1.7434 (10)	C5—H5	0.93
N1—C7	1.3016 (13)	C9—H9	0.93
N1—C6	1.3732 (12)	C14—C13	1.3792 (15)
N2—C11	1.3792 (12)	C14—C15	1.3878 (14)
N2—C10	1.4388 (13)	C14—H14	0.93
N2—H18	0.86	C11—C12	1.4011 (14)
F1—C13	1.3661 (12)	C11—C15	1.4077 (14)
C7—C8	1.4217 (13)	C2—C3	1.3700 (14)
C1—C9	1.4133 (13)	C2—H17	0.93
C1—C6	1.4149 (13)	C13—C16	1.3737 (15)
C1—C2	1.4164 (13)	C3—C4	1.4128 (15)
C10—C8	1.5161 (13)	C3—H3	0.93
C10—H10A	0.97	C12—C16	1.3936 (14)
C10—H10B	0.97	C12—H12	0.93
C8—C9	1.3714 (13)	C4—H4	0.93
C5—C4	1.3726 (15)	C15—H15	0.93
C5—C6	1.4136 (13)	C16—H16	0.93

C7—N1—C6	117.48 (8)	C13—C14—C15	118.66 (10)
C11—N2—C10	121.76 (8)	C13—C14—H14	120.7
C11—N2—H18	119.1	C15—C14—H14	120.7
C10—N2—H18	119.1	N2—C11—C12	122.23 (9)
N1—C7—C8	126.51 (9)	N2—C11—C15	119.59 (9)
N1—C7—Cl1	115.47 (7)	C12—C11—C15	118.18 (9)
C8—C7—Cl1	118.01 (7)	C3—C2—C1	120.15 (9)
C9—C1—C6	117.92 (9)	C3—C2—H17	119.9
C9—C1—C2	123.09 (9)	C1—C2—H17	119.9
C6—C1—C2	118.98 (9)	F1—C13—C16	119.13 (9)
N2—C10—C8	113.32 (8)	F1—C13—C14	118.49 (9)
N2—C10—H10A	108.9	C16—C13—C14	122.38 (10)
C8—C10—H10A	108.9	C2—C3—C4	120.64 (9)
N2—C10—H10B	108.9	C2—C3—H3	119.7
C8—C10—H10B	108.9	C4—C3—H3	119.7
H10A—C10—H10B	107.7	C16—C12—C11	120.86 (9)
C9—C8—C7	115.61 (8)	C16—C12—H12	119.6
C9—C8—C10	122.70 (8)	C11—C12—H12	119.6
C7—C8—C10	121.69 (8)	C5—C4—C3	120.52 (9)
C4—C5—C6	119.71 (9)	C5—C4—H4	119.7
C4—C5—H5	120.1	C3—C4—H4	119.7
C6—C5—H5	120.1	C14—C15—C11	121.05 (9)
N1—C6—C5	118.51 (9)	C14—C15—H15	119.5
N1—C6—C1	121.50 (9)	C11—C15—H15	119.5
C5—C6—C1	119.99 (9)	C13—C16—C12	118.87 (9)
C8—C9—C1	120.95 (9)	C13—C16—H16	120.6
C8—C9—H9	119.5	C12—C16—H16	120.6
C1—C9—H9	119.5

C6—N1—C7—C8	−0.94 (15)	C6—C1—C9—C8	−1.63 (14)
C6—N1—C7—Cl1	179.70 (7)	C2—C1—C9—C8	179.30 (9)
C11—N2—C10—C8	−82.06 (11)	C10—N2—C11—C12	4.96 (14)
N1—C7—C8—C9	0.82 (15)	C10—N2—C11—C15	−174.83 (9)
Cl1—C7—C8—C9	−179.83 (7)	C9—C1—C2—C3	178.48 (9)
N1—C7—C8—C10	−178.91 (9)	C6—C1—C2—C3	−0.58 (15)
Cl1—C7—C8—C10	0.43 (13)	C15—C14—C13—F1	−179.04 (9)
N2—C10—C8—C9	−14.02 (13)	C15—C14—C13—C16	0.18 (16)
N2—C10—C8—C7	165.69 (9)	C1—C2—C3—C4	0.04 (16)
C7—N1—C6—C5	179.69 (9)	N2—C11—C12—C16	−178.83 (9)
C7—N1—C6—C1	−0.29 (14)	C15—C11—C12—C16	0.96 (14)
C4—C5—C6—N1	179.83 (9)	C6—C5—C4—C3	−0.37 (16)
C4—C5—C6—C1	−0.19 (15)	C2—C3—C4—C5	0.44 (16)
C9—C1—C6—N1	1.53 (14)	C13—C14—C15—C11	0.14 (16)
C2—C1—C6—N1	−179.36 (9)	N2—C11—C15—C14	179.10 (9)
C9—C1—C6—C5	−178.45 (9)	C12—C11—C15—C14	−0.70 (15)
C2—C1—C6—C5	0.65 (14)	F1—C13—C16—C12	179.30 (9)
C7—C8—C9—C1	0.55 (14)	C14—C13—C16—C12	0.08 (16)
C10—C8—C9—C1	−179.73 (8)	C11—C12—C16—C13	−0.67 (15)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C11–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H18···N1ⁱ	0.86	2.30	3.1353 (12)	165
C4—H4···Cg2ⁱⁱ	0.93	2.91	3.7494 (13)	151
C10—H10A···Cg1ⁱⁱⁱ	0.97	2.62	3.5365 (12)	157
C10—H10B···Cg2^iv	0.97	2.98	3.8083 (11)	145

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂ClFN₂
M_r	286.73
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.3661 (8), 8.8967 (9), 11.5129 (12)
α, β, γ (°)	68.704 (1), 74.468 (1), 75.445 (1)
V (Å³)	667.25 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.55 × 0.50 × 0.25

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.858, 0.932
No. of measured, independent and observed [I > 2σ(I)] reflections	8162, 3930, 3633
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.733

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.094, 1.03
No. of reflections	3930
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.30

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C11–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H18···N1ⁱ	0.86	2.30	3.1353 (12)	165
C4—H4···Cg2ⁱⁱ	0.93	2.91	3.7494 (13)	151
C10—H10A···Cg1ⁱⁱⁱ	0.97	2.62	3.5365 (12)	157
C10—H10B···Cg2^iv	0.97	2.98	3.8083 (11)	145

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

Acknowledgements

JPJ thanks Dr Matthias Zeller and the YSU Department of Chemistry for their assistance with the data collection. The diffractometer was funded by NSF grant 0087210, by the Ohio Board of Regents grant CAP-491, and by YSU. CSC thanks the University of Mysore for research facilities and HSY thanks the University of Mysore for sabbatical leave.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA Google Scholar
Butcher, R. J., Jasinski, J. P., Mayekar, A. N., Yathirajan, H. S. & Narayana, B. (2007). Acta Cryst. E63, o3603. Web of Science CSD CrossRef IUCr Journals Google Scholar
Campbell, S. F., Hardstone, J. D. & Palmer, M. J. (1988). J. Med. Chem. 31, 1031–1035. CrossRef CAS PubMed Web of Science Google Scholar
Dutta, N. J., Khunt, R. C. & Parikh, A. R. (2002). Indian J. Chem. Sect. B, 41, 433–435. Google Scholar
Khan, F. N., Mohana Roopan, S., Hathwar, V. R. & Ng, S. W. (2010). Acta Cryst. E66, o201. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kouznetsov, V. V., Vargas Mendez, L. Y. & Melendez Gomez, C. M. (2005). Curr. Org. Chem. 9, 141–161. Web of Science CrossRef CAS Google Scholar
Lynch, D. E. & McClenaghan, I. (2001). Acta Cryst. E57, o54–o55. Web of Science CSD CrossRef IUCr Journals Google Scholar
Markees, D. G., Dewey, V. C. & Kidder, G. W. (1970). J. Med. Chem. 13, 324–326. CrossRef CAS PubMed Web of Science Google Scholar
Meth-Cohn, O., Tarnowski, B., Hayear, R., Keyzad, A. & Rhouti, S. (1981). J. Chem. Soc. Perkin Trans. 1, pp. 2509–2517. CrossRef Web of Science Google Scholar
Michael, J. P. (1997). Nat. Prod. Rep. 14, 605–608. CrossRef CAS Web of Science Google Scholar
Morimoto, Y., Matsuda, F. & Shirahama, H. (1991). Synlett, 3, 202–203. CrossRef Google Scholar
Padwa, A., Brodney, M. A., Liu, B., Satake, K. & Wu, T. (1999). J. Org. Chem. 64, 3595–3607. Web of Science CrossRef PubMed CAS Google Scholar
Rajendran, P. & Karavembu, R. (2002). Indian J. Chem. Sect. B, 41, 222–224. Google Scholar
Robert, A. & Meunier, B. (1998). Chem. Soc. Rev. 27, 273–279. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Subashini, R., Khan, F. N., Kumar, R., Hathwar, V. R. & Ng, S. W. (2009). Acta Cryst. E65, o2721. Web of Science CrossRef IUCr Journals Google Scholar
Wu, T.-Q., Wang, J.-H., Shen, F. & Hu, A.-X. (2009). Acta Cryst. E65, o1463. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yathirajan, H. S., Sreevidya, T. V., Prathap, M., Narayana, B. & Bolte, M. (2007). Acta Cryst. E63, o763–o765. 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages o2548-o2549

doi:10.1107/S1600536810036056

Open

access