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

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 1| January 2016| x152460
doi:10.1107/S2414314615024608

1-[5-(2-Chloro­phen­yl)-3-(4-methyl­phen­yl)-4,5-di­hydro-1H-pyrazol-1-yl]ethan-1-one

Farook Adam,a* Nadiah Ameram,a Seranthimata Samshuddin,b Moonnanjilikkal Brighten Antonyb and Musthakeem Ali Khanb

aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 Pulau, Pinang, Malaysia, and bDepartment of P.G. Studies in Chemistry, Alvas 5, 6 College, Moodbidri, Karnataka 574 227, India
*Correspondence e-mail: farook@usm.my

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 20 December 2015; accepted 21 December 2015; online 12 January 2016)

The title compound, C18H17ClN2O, crystallized with two independent mol­ecules (the S and R enanti­omers) in the asymmetric unit. The mol­ecules are V-shaped with the two aromatic rings inclined to one another by 78.78 (11) and 81.23 (11)°. In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds, forming chains along the c-axis direction. The chains are linked via C—H⋯π inter­actions, forming a three-dimensional framework. The crystal structure was refined as a two-component twin.

CCDC reference: 1443745

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Pyrazoline derivatives are well known for their versatile pharmacological activities (Sarojini et al., 2010[Sarojini, B. K., Vidyagayatri, M., Darshanraj, C. G., Bharath, B. R. & Manjunatha, H. (2010). Lett. Drug. Des. Discov. 7, 214-224.]; Samshuddin et al., 2012[Samshuddin, S., Narayana, B., Sarojini, B. K., Khan, M. T. H., Yathirajan, H. S., Raj, C. G. D. & Raghavendra, R. (2012). Med. Chem. Res. 21, 2012-2022.]). Many 1,3,5-triaryl-2-pyrazolines have a variety of industrial applications; used as scintillation solutes (Wiley et al., 1958[Wiley, R. H., Jarboe, C. H., Hayes, F. N., Hansbury, E., Nielsen, J. T., Callahan, P. X. & Sellars, M. C. (1958). J. Org. Chem. 23, 732-738.]) and as fluorescent agents (Zhi-Yun et al., 1999[Zhi-Yun, L. U., Wei-Guo, Z. H. U., Qing, J. & Ming-Gui, X. I. E. (1999). Chin. Chem. Lett. 10, 679-682.]). In view of the importance of pyrazolines the title compound, a new N-acetyl substituted pyrazoline derivative, was prepared by the condensation of (2E)-3-(2-chloro­phen­yl)-1-(4-methyl­phen­yl)prop-2-en-1-one and hydrazine hydrate in the presence of acetic acid.

The title compound, Fig. 1[link], crystallized with two independent mol­ecules (A and B: the S and R enanti­omers, respectively) in the asymmetric unit. The pyrazole ring in mol­ecule A has an envelope conformation with the chiral C atom, C7A, as the flap. In mol­ecule B the pyrazole ring has a twist conformation on the CH—CH2 (C7B—C8B) bond. Their mean planes are inclined to the 4-methyl­benzene ring by 5.65 (12)° in A and by 8.99 (12)° in B. The two aromatic rings are inclined to one another by 78.78 (11)° in mol­ecule A and by 81.23 (11)° in mol­ecule B.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound, showin the atom labelling and 50% probability displacement ellipsoids.

In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds, forming chains along [001]; see Table 1[link] and Fig. 2[link]. The chains are linked via C—H⋯π inter­actions forming a three-dimensional framework (Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 and Cg6 are the centroids of rings C10A–C15A and C10B–C15B, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C8A—H8AB⋯O1Bi 0.99 2.48 3.362 (3) 149
C11B—H11B⋯O1Aii 0.95 2.56 3.458 (3) 159
C8B—H8BA⋯O1A 0.99 2.42 3.319 (3) 151
C3A—H3AA⋯Cg6iii 0.95 2.69 3.550 (3) 151
C3B—H3BA⋯Cg3iv 0.95 2.95 3.616 (3) 128
Symmetry codes: (i) x, y, z-1; (ii) -x, -y, -z+1; (iii) -x+1, -y, -z+1; (iv) -x+1, -y+1, -z+1.
[Figure 2]
Figure 2
The crystal packing of the title compound viewed along the b axis. Hydrogen bonds are shown as dashed lines (see Table 1[link]).

Synthesis and crystallization

A mixture of (2E)-3-(2-chloro­phen­yl)-1-(4-methyl­phen­yl)prop-2-en-1-one (2.56 g, 0.01 mol) and hydrazine hydrate (1 ml) in 30 ml acetic acid was refluxed for 8 h. The reaction mixture was cooled and poured into 100 ml ice-cold water. The precipitate was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from ethanol by slow evaporation (yield 70%; m.p. 409–412 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The crystal structure was refined as a 2-component twin [180° rotation about the b* axis; BASF = 0.431 (1)].

Table 2
Experimental details

Crystal data
Chemical formula C18H17ClN2O
Mr 312.79
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 100
a, b, c (Å) 11.0767 (12), 12.0670 (13), 12.1600 (13)
α, β, γ (°) 90.825 (2), 102.5614 (19), 95.142 (2)
V (Å3) 1579.1 (3)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.25
Crystal size (mm) 0.49 × 0.31 × 0.29
 
Data collection
Diffractometer Bruker APEX DUO CCD area-detector diffractometer
Absorption correction Multi-scan (TWINABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.711, 0.857
No. of measured, independent and observed [I > 2σ(I)] reflections 5665, 5665, 5334
Rint ?
(sin θ/λ)max (Å−1) 0.597
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.119, 1.10
No. of reflections 5665
No. of parameters 402
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.34, −0.35
Computer programs: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data

CCDC reference: 1443745

Crystal structure: contains datablocks I, Global. DOI: 10.1107/S2414314615024608/su4006sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314615024608/su4006Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314615024608/su4006Isup3.cml

checkCIF report


Experimental top

A mixture of (2E)-3-(2-chlorophenyl)-1-(4-methylphenyl)prop-2-en-1-one (2.56 g, 0.01 mol) and hydrazine hydrate (1 ml) in 30 ml acetic acid was refluxed for 8 h. The reaction mixture was cooled and poured into 100 ml ice-cold water. The precipitate was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from ethanol by slow evaporation (yield 70%; m.p. 409–412 K).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The crystal structure was refined as a 2-component twin [180° rotation about the b* axis; BASF = 0.431 (1)].

Structure description top

Pyrazoline derivatives are well known for their versatile pharmacological activities (Sarojini et al., 2010; Samshuddin et al., 2012). Many 1,3,5-triaryl-2-pyrazolines have a variety of industrial application; used as scintillation solutes (Wiley et al., 1958) and as fluorescent agents (Zhi-Yun et al., 1999). In view of the importance of pyrazolines the title compound, new N-acetyl substituted pyrazoline derivative, was prepared by the condensation of (2E)-3-(2-chlorophenyl)-1-(4-methylphenyl)prop-2-en-1-one and hydrazine hydrate in the presence of acetic acid.

The title compound, Fig. 1, crystallized with two independent molecules (A and B: the S and R enantiomers, respectively) in the asymmetric unit. The pyrazole ring in molecule A has an envelope conformation with the chiral C atom, C7A, as the flap. In molecule B the pyrazole ring has a twist conformation on the CH—CH2 (C7B—C8B) bond. Their mean planes are inclined to the 4-methylbenzene ring by 5.65 (12)° in A and by 8.99 (12)° in B. The two aromatic rings are inclined to one another by 78.78 (11)° in molecule A and by 81.23 (11)° in molecule B.

In the crystal, molecules are linked via C—H···O hydrogen bonds, forming chains along [001]; see Table 1 and Fig. 2. The chains are linked via C—H···π interactions forming a three-dimensional framework (Table 1).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showin the atom labelling and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed along the b axis. Hydrogen bonds are shown as dashed lines (see Table 1).
1-[5-(2-Chlorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethan-1-one top
Crystal data top
C18H17ClN2OZ = 4
Mr = 312.79F(000) = 656
Triclinic, P1Dx = 1.316 Mg m−3
a = 11.0767 (12) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.0670 (13) ÅCell parameters from 9954 reflections
c = 12.1600 (13) Åθ = 2.3–25.1°
α = 90.825 (2)°µ = 0.25 mm−1
β = 102.5614 (19)°T = 100 K
γ = 95.142 (2)°Block, colourless
V = 1579.1 (3) Å30.49 × 0.31 × 0.29 mm
Data collection top
Bruker APEX DUO CCD area-detector
diffractometer		5665 independent reflections
Radiation source: fine-focus sealed tube5334 reflections with I > 2σ(I)
Graphite monochromatorθmax = 25.1°, θmin = 1.7°
φ and ω scansh = −13→12
Absorption correction: multi-scan
(TWINABS; Bruker, 2009)		k = −14→14
Tmin = 0.711, Tmax = 0.857l = 0→14
5665 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.119 w = 1/[σ2(Fo2) + (0.0832P)2 + 0.2751P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
5665 reflectionsΔρmax = 0.34 e Å−3
402 parametersΔρmin = −0.35 e Å−3
Crystal data top
C18H17ClN2Oγ = 95.142 (2)°
Mr = 312.79V = 1579.1 (3) Å3
Triclinic, P1Z = 4
a = 11.0767 (12) ÅMo Kα radiation
b = 12.0670 (13) ŵ = 0.25 mm−1
c = 12.1600 (13) ÅT = 100 K
α = 90.825 (2)°0.49 × 0.31 × 0.29 mm
β = 102.5614 (19)°
Data collection top
Bruker APEX DUO CCD area-detector
diffractometer		5665 measured reflections
Absorption correction: multi-scan
(TWINABS; Bruker, 2009)		5665 independent reflections
Tmin = 0.711, Tmax = 0.8575334 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.119H-atom parameters constrained
S = 1.10Δρmax = 0.34 e Å−3
5665 reflectionsΔρmin = −0.35 e Å−3
402 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. Refined as a 2-component twin

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl1A0.21908 (7)0.08540 (5)0.04400 (6)0.03442 (17)
O1A0.03134 (16)0.25816 (14)0.32387 (14)0.0274 (4)
N1A0.09059 (18)0.37602 (16)0.20123 (16)0.0204 (4)
N2A0.10951 (17)0.48329 (16)0.16358 (16)0.0187 (4)
C1A0.3041 (2)0.1604 (2)0.1639 (2)0.0240 (5)
C2A0.4170 (3)0.1255 (2)0.2180 (2)0.0345 (6)
H2AA0.44660.06100.19120.041*
C3A0.4860 (2)0.1861 (3)0.3118 (2)0.0350 (6)
H3AA0.56320.16280.35030.042*
C4A0.4431 (2)0.2799 (2)0.3495 (2)0.0305 (6)
H4AA0.49110.32170.41340.037*
C5A0.3302 (2)0.3133 (2)0.2942 (2)0.0240 (5)
H5AA0.30160.37820.32100.029*
C6A0.2577 (2)0.25441 (18)0.20064 (19)0.0195 (5)
C7A0.1359 (2)0.29186 (19)0.13625 (19)0.0194 (5)
H7AA0.07200.22690.11390.023*
C8A0.1540 (2)0.35784 (18)0.03170 (19)0.0202 (5)
H8AA0.23570.34840.01400.024*
H8AB0.08730.3351−0.03530.024*
C9A0.14683 (19)0.47560 (19)0.07111 (18)0.0178 (4)
C10A0.17624 (19)0.57493 (18)0.01095 (18)0.0176 (4)
C11A0.1686 (2)0.68142 (19)0.05564 (19)0.0208 (5)
H11A0.14400.68910.12530.025*
C12A0.1967 (2)0.7746 (2)−0.0014 (2)0.0238 (5)
H12A0.19000.84610.02920.029*
C13A0.2347 (2)0.7666 (2)−0.1027 (2)0.0220 (5)
C14A0.2435 (2)0.6615 (2)−0.1464 (2)0.0229 (5)
H14A0.26980.6544−0.21530.027*
C15A0.2146 (2)0.56628 (19)−0.09058 (19)0.0211 (5)
H15A0.22090.4949−0.12180.025*
C16A0.0419 (2)0.3539 (2)0.2927 (2)0.0222 (5)
C17A0.0064 (2)0.4513 (2)0.3527 (2)0.0274 (5)
H17A−0.01230.51120.29990.041*
H17B0.07540.47800.41510.041*
H17C−0.06710.42830.38240.041*
C18A0.2599 (3)0.8699 (2)−0.1655 (2)0.0310 (6)
H18A0.31820.9237−0.11460.047*
H18B0.18180.9030−0.19360.047*
H18C0.29590.8503−0.22910.047*
Cl1B0.31200 (6)0.46911 (5)0.58780 (6)0.03452 (17)
O1B0.02652 (17)0.27178 (15)0.76408 (14)0.0297 (4)
N1B0.11108 (19)0.15285 (16)0.66688 (16)0.0213 (4)
N2B0.12585 (17)0.04611 (15)0.63221 (16)0.0194 (4)
C1B0.3553 (2)0.3952 (2)0.7108 (2)0.0249 (5)
C2B0.4501 (2)0.4432 (2)0.7954 (2)0.0318 (6)
H2BA0.48810.51560.78770.038*
C3B0.4892 (2)0.3849 (3)0.8915 (2)0.0380 (7)
H3BA0.55470.41690.95020.046*
C4B0.4327 (2)0.2796 (3)0.9023 (2)0.0365 (6)
H4BA0.46020.23900.96790.044*
C5B0.3363 (2)0.2337 (2)0.8175 (2)0.0292 (5)
H5BA0.29760.16180.82590.035*
C6B0.2944 (2)0.2914 (2)0.71936 (19)0.0221 (5)
C7B0.1899 (2)0.23941 (19)0.62557 (19)0.0206 (5)
H7BA0.13880.29800.58790.025*
C8B0.2386 (2)0.17185 (19)0.53747 (19)0.0222 (5)
H8BA0.19970.19050.45950.027*
H8BB0.33000.18480.54880.027*
C9B0.1987 (2)0.05402 (18)0.56220 (18)0.0183 (5)
C10B0.2338 (2)−0.04471 (19)0.51034 (19)0.0194 (5)
C11B0.1761 (2)−0.15102 (19)0.52063 (19)0.0202 (5)
H11B0.1133−0.16010.56290.024*
C12B0.2099 (2)−0.2424 (2)0.4697 (2)0.0243 (5)
H12B0.1704−0.31400.47790.029*
C13B0.3016 (2)−0.2322 (2)0.4060 (2)0.0239 (5)
C14B0.3578 (2)−0.1270 (2)0.3965 (2)0.0245 (5)
H14B0.4204−0.11810.35400.029*
C15B0.3254 (2)−0.0342 (2)0.44718 (19)0.0219 (5)
H15B0.36550.03710.43900.026*
C16B0.0340 (2)0.1753 (2)0.73584 (19)0.0235 (5)
C17B−0.0383 (2)0.0777 (2)0.7745 (2)0.0286 (5)
H17D−0.03570.01140.72780.043*
H17E−0.12480.09380.76740.043*
H17F−0.00170.06430.85350.043*
C18B0.3362 (3)−0.3328 (2)0.3498 (2)0.0321 (6)
H18D0.2606−0.37860.31210.048*
H18E0.3865−0.37640.40660.048*
H18F0.3841−0.30880.29390.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0516 (4)0.0218 (3)0.0306 (3)0.0038 (3)0.0108 (3)−0.0039 (2)
O1A0.0261 (9)0.0289 (9)0.0274 (9)0.0012 (7)0.0065 (7)0.0094 (7)
N1A0.0215 (10)0.0197 (9)0.0215 (10)0.0038 (8)0.0071 (8)0.0035 (8)
N2A0.0166 (9)0.0203 (9)0.0193 (9)0.0019 (7)0.0039 (7)0.0031 (7)
C1A0.0285 (12)0.0234 (12)0.0217 (12)0.0027 (10)0.0089 (10)0.0059 (9)
C2A0.0416 (16)0.0355 (14)0.0361 (15)0.0198 (12)0.0221 (13)0.0154 (12)
C3A0.0187 (12)0.0581 (18)0.0316 (14)0.0114 (12)0.0082 (10)0.0222 (13)
C4A0.0204 (12)0.0435 (15)0.0239 (12)−0.0046 (11)−0.0002 (10)0.0084 (11)
C5A0.0199 (12)0.0261 (12)0.0249 (12)−0.0029 (9)0.0045 (9)0.0044 (9)
C6A0.0199 (11)0.0190 (11)0.0209 (11)−0.0014 (9)0.0081 (9)0.0062 (9)
C7A0.0208 (11)0.0182 (11)0.0191 (11)0.0017 (9)0.0039 (9)0.0010 (8)
C8A0.0224 (12)0.0206 (11)0.0180 (11)0.0035 (9)0.0044 (9)0.0009 (9)
C9A0.0120 (10)0.0233 (11)0.0164 (10)0.0030 (9)−0.0006 (8)−0.0002 (9)
C10A0.0116 (10)0.0227 (11)0.0179 (11)0.0022 (8)0.0013 (8)0.0011 (9)
C11A0.0182 (11)0.0264 (12)0.0184 (11)0.0029 (9)0.0049 (9)0.0016 (9)
C12A0.0250 (12)0.0198 (11)0.0272 (12)0.0037 (9)0.0062 (10)0.0004 (9)
C13A0.0168 (11)0.0251 (11)0.0237 (11)0.0019 (9)0.0034 (9)0.0051 (9)
C14A0.0187 (11)0.0332 (13)0.0179 (11)0.0040 (9)0.0060 (9)0.0011 (9)
C15A0.0182 (11)0.0242 (11)0.0197 (11)0.0038 (9)0.0013 (9)−0.0009 (9)
C16A0.0146 (11)0.0321 (13)0.0197 (11)0.0024 (9)0.0028 (9)0.0044 (10)
C17A0.0258 (12)0.0362 (14)0.0217 (12)0.0028 (10)0.0087 (10)0.0014 (10)
C18A0.0360 (15)0.0280 (13)0.0325 (14)0.0045 (11)0.0139 (12)0.0080 (11)
Cl1B0.0337 (3)0.0277 (3)0.0408 (4)−0.0019 (3)0.0069 (3)0.0074 (3)
O1B0.0291 (9)0.0328 (10)0.0269 (9)0.0100 (8)0.0032 (7)−0.0061 (7)
N1B0.0205 (10)0.0215 (10)0.0223 (10)0.0029 (8)0.0053 (8)0.0004 (8)
N2B0.0187 (9)0.0198 (9)0.0196 (9)0.0019 (7)0.0038 (8)−0.0006 (7)
C1B0.0217 (12)0.0279 (12)0.0272 (13)0.0030 (10)0.0097 (10)−0.0031 (10)
C2B0.0185 (12)0.0384 (15)0.0388 (15)−0.0025 (11)0.0099 (11)−0.0140 (12)
C3B0.0151 (12)0.066 (2)0.0313 (15)−0.0015 (12)0.0050 (11)−0.0158 (13)
C4B0.0229 (13)0.0617 (19)0.0241 (13)0.0077 (13)0.0014 (10)0.0039 (12)
C5B0.0245 (12)0.0385 (14)0.0238 (12)0.0054 (11)0.0030 (10)0.0025 (11)
C6B0.0200 (12)0.0265 (12)0.0200 (11)0.0039 (10)0.0046 (9)−0.0025 (9)
C7B0.0211 (11)0.0206 (11)0.0195 (11)0.0023 (9)0.0027 (9)0.0012 (9)
C8B0.0274 (12)0.0214 (11)0.0181 (11)0.0010 (9)0.0061 (9)0.0014 (9)
C9B0.0161 (11)0.0216 (11)0.0159 (10)0.0014 (9)0.0009 (8)0.0023 (8)
C10B0.0183 (11)0.0242 (11)0.0152 (10)0.0022 (9)0.0028 (8)0.0025 (9)
C11B0.0170 (11)0.0239 (11)0.0187 (11)0.0005 (9)0.0025 (9)0.0016 (9)
C12B0.0266 (12)0.0204 (11)0.0238 (12)0.0009 (9)0.0013 (10)0.0014 (9)
C13B0.0244 (12)0.0286 (12)0.0173 (11)0.0072 (10)−0.0001 (9)−0.0030 (9)
C14B0.0215 (12)0.0328 (13)0.0200 (11)0.0032 (10)0.0062 (9)−0.0008 (10)
C15B0.0199 (11)0.0255 (11)0.0204 (11)0.0005 (9)0.0052 (9)0.0023 (9)
C16B0.0170 (11)0.0342 (13)0.0182 (10)0.0049 (10)0.0005 (9)−0.0008 (10)
C17B0.0218 (12)0.0425 (14)0.0229 (12)0.0027 (11)0.0080 (10)−0.0001 (11)
C18B0.0371 (15)0.0338 (14)0.0245 (13)0.0074 (12)0.0036 (11)−0.0043 (11)
Geometric parameters (Å, º) top
Cl1A—C1A1.744 (3)Cl1B—C1B1.751 (3)
O1A—C16A1.225 (3)O1B—C16B1.225 (3)
N1A—C16A1.357 (3)N1B—C16B1.361 (3)
N1A—N2A1.393 (3)N1B—N2B1.384 (3)
N1A—C7A1.466 (3)N1B—C7B1.466 (3)
N2A—C9A1.285 (3)N2B—C9B1.293 (3)
C1A—C2A1.385 (4)C1B—C2B1.379 (4)
C1A—C6A1.394 (3)C1B—C6B1.385 (4)
C2A—C3A1.385 (4)C2B—C3B1.380 (4)
C2A—H2AA0.9500C2B—H2BA0.9500
C3A—C4A1.376 (4)C3B—C4B1.386 (4)
C3A—H3AA0.9500C3B—H3BA0.9500
C4A—C5A1.383 (4)C4B—C5B1.381 (4)
C4A—H4AA0.9500C4B—H4BA0.9500
C5A—C6A1.386 (3)C5B—C6B1.401 (3)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—C7A1.515 (3)C6B—C7B1.519 (3)
C7A—C8A1.550 (3)C7B—C8B1.551 (3)
C7A—H7AA1.0000C7B—H7BA1.0000
C8A—C9A1.508 (3)C8B—C9B1.505 (3)
C8A—H8AA0.9900C8B—H8BA0.9900
C8A—H8AB0.9900C8B—H8BB0.9900
C9A—C10A1.462 (3)C9B—C10B1.462 (3)
C10A—C15A1.396 (3)C10B—C15B1.397 (3)
C10A—C11A1.405 (3)C10B—C11B1.401 (3)
C11A—C12A1.377 (3)C11B—C12B1.377 (3)
C11A—H11A0.9500C11B—H11B0.9500
C12A—C13A1.390 (3)C12B—C13B1.403 (4)
C12A—H12A0.9500C12B—H12B0.9500
C13A—C14A1.388 (3)C13B—C14B1.381 (4)
C13A—C18A1.508 (3)C13B—C18B1.504 (3)
C14A—C15A1.391 (3)C14B—C15B1.383 (3)
C14A—H14A0.9500C14B—H14B0.9500
C15A—H15A0.9500C15B—H15B0.9500
C16A—C17A1.501 (3)C16B—C17B1.503 (4)
C17A—H17A0.9800C17B—H17D0.9800
C17A—H17B0.9800C17B—H17E0.9800
C17A—H17C0.9800C17B—H17F0.9800
C18A—H18A0.9800C18B—H18D0.9800
C18A—H18B0.9800C18B—H18E0.9800
C18A—H18C0.9800C18B—H18F0.9800
C16A—N1A—N2A122.91 (19)C16B—N1B—N2B123.3 (2)
C16A—N1A—C7A124.13 (19)C16B—N1B—C7B123.1 (2)
N2A—N1A—C7A112.85 (17)N2B—N1B—C7B113.53 (18)
C9A—N2A—N1A107.83 (18)C9B—N2B—N1B107.86 (18)
C2A—C1A—C6A122.2 (2)C2B—C1B—C6B122.6 (2)
C2A—C1A—Cl1A118.7 (2)C2B—C1B—Cl1B118.1 (2)
C6A—C1A—Cl1A119.08 (19)C6B—C1B—Cl1B119.29 (19)
C3A—C2A—C1A118.9 (2)C1B—C2B—C3B119.2 (3)
C3A—C2A—H2AA120.6C1B—C2B—H2BA120.4
C1A—C2A—H2AA120.6C3B—C2B—H2BA120.4
C4A—C3A—C2A120.2 (2)C2B—C3B—C4B120.0 (2)
C4A—C3A—H3AA119.9C2B—C3B—H3BA120.0
C2A—C3A—H3AA119.9C4B—C3B—H3BA120.0
C3A—C4A—C5A120.0 (2)C5B—C4B—C3B119.9 (3)
C3A—C4A—H4AA120.0C5B—C4B—H4BA120.0
C5A—C4A—H4AA120.0C3B—C4B—H4BA120.0
C4A—C5A—C6A121.7 (2)C4B—C5B—C6B121.3 (3)
C4A—C5A—H5AA119.2C4B—C5B—H5BA119.4
C6A—C5A—H5AA119.2C6B—C5B—H5BA119.4
C5A—C6A—C1A117.0 (2)C1B—C6B—C5B116.9 (2)
C5A—C6A—C7A122.5 (2)C1B—C6B—C7B122.1 (2)
C1A—C6A—C7A120.4 (2)C5B—C6B—C7B120.9 (2)
N1A—C7A—C6A111.47 (19)N1B—C7B—C6B111.94 (18)
N1A—C7A—C8A101.24 (17)N1B—C7B—C8B101.23 (18)
C6A—C7A—C8A111.26 (19)C6B—C7B—C8B112.36 (19)
N1A—C7A—H7AA110.8N1B—C7B—H7BA110.3
C6A—C7A—H7AA110.8C6B—C7B—H7BA110.3
C8A—C7A—H7AA110.8C8B—C7B—H7BA110.3
C9A—C8A—C7A101.45 (17)C9B—C8B—C7B101.85 (18)
C9A—C8A—H8AA111.5C9B—C8B—H8BA111.4
C7A—C8A—H8AA111.5C7B—C8B—H8BA111.4
C9A—C8A—H8AB111.5C9B—C8B—H8BB111.4
C7A—C8A—H8AB111.5C7B—C8B—H8BB111.4
H8AA—C8A—H8AB109.3H8BA—C8B—H8BB109.3
N2A—C9A—C10A121.0 (2)N2B—C9B—C10B121.5 (2)
N2A—C9A—C8A114.3 (2)N2B—C9B—C8B114.06 (19)
C10A—C9A—C8A124.68 (19)C10B—C9B—C8B124.4 (2)
C15A—C10A—C11A118.7 (2)C15B—C10B—C11B118.4 (2)
C15A—C10A—C9A120.9 (2)C15B—C10B—C9B120.1 (2)
C11A—C10A—C9A120.4 (2)C11B—C10B—C9B121.5 (2)
C12A—C11A—C10A120.1 (2)C12B—C11B—C10B120.2 (2)
C12A—C11A—H11A120.0C12B—C11B—H11B119.9
C10A—C11A—H11A120.0C10B—C11B—H11B119.9
C11A—C12A—C13A121.6 (2)C11B—C12B—C13B121.5 (2)
C11A—C12A—H12A119.2C11B—C12B—H12B119.3
C13A—C12A—H12A119.2C13B—C12B—H12B119.3
C14A—C13A—C12A118.5 (2)C14B—C13B—C12B117.7 (2)
C14A—C13A—C18A121.2 (2)C14B—C13B—C18B121.5 (2)
C12A—C13A—C18A120.3 (2)C12B—C13B—C18B120.7 (2)
C13A—C14A—C15A120.9 (2)C13B—C14B—C15B121.7 (2)
C13A—C14A—H14A119.6C13B—C14B—H14B119.2
C15A—C14A—H14A119.6C15B—C14B—H14B119.2
C14A—C15A—C10A120.4 (2)C14B—C15B—C10B120.5 (2)
C14A—C15A—H15A119.8C14B—C15B—H15B119.8
C10A—C15A—H15A119.8C10B—C15B—H15B119.8
O1A—C16A—N1A119.9 (2)O1B—C16B—N1B119.8 (2)
O1A—C16A—C17A123.2 (2)O1B—C16B—C17B123.0 (2)
N1A—C16A—C17A116.9 (2)N1B—C16B—C17B117.2 (2)
C16A—C17A—H17A109.5C16B—C17B—H17D109.5
C16A—C17A—H17B109.5C16B—C17B—H17E109.5
H17A—C17A—H17B109.5H17D—C17B—H17E109.5
C16A—C17A—H17C109.5C16B—C17B—H17F109.5
H17A—C17A—H17C109.5H17D—C17B—H17F109.5
H17B—C17A—H17C109.5H17E—C17B—H17F109.5
C13A—C18A—H18A109.5C13B—C18B—H18D109.5
C13A—C18A—H18B109.5C13B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
C13A—C18A—H18C109.5C13B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
C16A—N1A—N2A—C9A−174.9 (2)C16B—N1B—N2B—C9B176.0 (2)
C7A—N1A—N2A—C9A8.8 (2)C7B—N1B—N2B—C9B−6.2 (2)
C6A—C1A—C2A—C3A0.0 (4)C6B—C1B—C2B—C3B1.9 (4)
Cl1A—C1A—C2A—C3A178.68 (19)Cl1B—C1B—C2B—C3B−177.57 (19)
C1A—C2A—C3A—C4A−0.6 (4)C1B—C2B—C3B—C4B−0.3 (4)
C2A—C3A—C4A—C5A0.6 (4)C2B—C3B—C4B—C5B−0.8 (4)
C3A—C4A—C5A—C6A0.0 (4)C3B—C4B—C5B—C6B0.5 (4)
C4A—C5A—C6A—C1A−0.6 (3)C2B—C1B—C6B—C5B−2.2 (3)
C4A—C5A—C6A—C7A−177.7 (2)Cl1B—C1B—C6B—C5B177.29 (18)
C2A—C1A—C6A—C5A0.6 (3)C2B—C1B—C6B—C7B180.0 (2)
Cl1A—C1A—C6A—C5A−178.08 (17)Cl1B—C1B—C6B—C7B−0.5 (3)
C2A—C1A—C6A—C7A177.8 (2)C4B—C5B—C6B—C1B1.0 (4)
Cl1A—C1A—C6A—C7A−0.9 (3)C4B—C5B—C6B—C7B178.8 (2)
C16A—N1A—C7A—C6A−72.6 (3)C16B—N1B—C7B—C6B69.3 (3)
N2A—N1A—C7A—C6A103.7 (2)N2B—N1B—C7B—C6B−108.6 (2)
C16A—N1A—C7A—C8A169.0 (2)C16B—N1B—C7B—C8B−170.9 (2)
N2A—N1A—C7A—C8A−14.7 (2)N2B—N1B—C7B—C8B11.3 (2)
C5A—C6A—C7A—N1A−15.5 (3)C1B—C6B—C7B—N1B−159.0 (2)
C1A—C6A—C7A—N1A167.55 (19)C5B—C6B—C7B—N1B23.2 (3)
C5A—C6A—C7A—C8A96.8 (3)C1B—C6B—C7B—C8B87.8 (3)
C1A—C6A—C7A—C8A−80.2 (3)C5B—C6B—C7B—C8B−89.9 (3)
N1A—C7A—C8A—C9A14.0 (2)N1B—C7B—C8B—C9B−11.2 (2)
C6A—C7A—C8A—C9A−104.6 (2)C6B—C7B—C8B—C9B108.4 (2)
N1A—N2A—C9A—C10A−179.30 (19)N1B—N2B—C9B—C10B179.58 (19)
N1A—N2A—C9A—C8A1.9 (2)N1B—N2B—C9B—C8B−2.4 (3)
C7A—C8A—C9A—N2A−10.7 (2)C7B—C8B—C9B—N2B9.1 (3)
C7A—C8A—C9A—C10A170.6 (2)C7B—C8B—C9B—C10B−173.0 (2)
N2A—C9A—C10A—C15A−178.8 (2)N2B—C9B—C10B—C15B−171.4 (2)
C8A—C9A—C10A—C15A−0.1 (3)C8B—C9B—C10B—C15B10.8 (3)
N2A—C9A—C10A—C11A2.4 (3)N2B—C9B—C10B—C11B9.7 (3)
C8A—C9A—C10A—C11A−179.0 (2)C8B—C9B—C10B—C11B−168.1 (2)
C15A—C10A—C11A—C12A1.0 (3)C15B—C10B—C11B—C12B0.3 (3)
C9A—C10A—C11A—C12A179.9 (2)C9B—C10B—C11B—C12B179.2 (2)
C10A—C11A—C12A—C13A−0.9 (4)C10B—C11B—C12B—C13B−0.5 (3)
C11A—C12A—C13A—C14A0.2 (4)C11B—C12B—C13B—C14B0.5 (3)
C11A—C12A—C13A—C18A177.5 (2)C11B—C12B—C13B—C18B−179.2 (2)
C12A—C13A—C14A—C15A0.3 (3)C12B—C13B—C14B—C15B−0.3 (4)
C18A—C13A—C14A—C15A−177.0 (2)C18B—C13B—C14B—C15B179.3 (2)
C13A—C14A—C15A—C10A−0.2 (3)C13B—C14B—C15B—C10B0.1 (4)
C11A—C10A—C15A—C14A−0.5 (3)C11B—C10B—C15B—C14B−0.1 (3)
C9A—C10A—C15A—C14A−179.3 (2)C9B—C10B—C15B—C14B−179.1 (2)
N2A—N1A—C16A—O1A−177.6 (2)N2B—N1B—C16B—O1B179.2 (2)
C7A—N1A—C16A—O1A−1.6 (3)C7B—N1B—C16B—O1B1.6 (3)
N2A—N1A—C16A—C17A0.9 (3)N2B—N1B—C16B—C17B−0.4 (3)
C7A—N1A—C16A—C17A176.8 (2)C7B—N1B—C16B—C17B−178.1 (2)
Hydrogen-bond geometry (Å, º) top
Cg3 and Cg6 are the centroids of rings C10A–C15A and C10B–C15B, respectively.
D—H···AD—HH···AD···AD—H···A
C8A—H8AB···O1Bi0.992.483.362 (3)149
C11B—H11B···O1Aii0.952.563.458 (3)159
C8B—H8BA···O1A0.992.423.319 (3)151
C3A—H3AA···Cg6iii0.952.693.550 (3)151
C3B—H3BA···Cg3iv0.952.953.616 (3)128
Symmetry codes: (i) x, y, z−1; (ii) −x, −y, −z+1; (iii) −x+1, −y, −z+1; (iv) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
Cg3 and Cg6 are the centroids of rings C10A–C15A and C10B–C15B, respectively.
D—H···AD—HH···AD···AD—H···A
C8A—H8AB···O1Bi0.992.483.362 (3)149
C11B—H11B···O1Aii0.952.563.458 (3)159
C8B—H8BA···O1A0.992.423.319 (3)151
C3A—H3AA···Cg6iii0.952.693.550 (3)151
C3B—H3BA···Cg3iv0.952.953.616 (3)128
Symmetry codes: (i) x, y, z−1; (ii) −x, −y, −z+1; (iii) −x+1, −y, −z+1; (iv) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC18H17ClN2O
Mr312.79
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)11.0767 (12), 12.0670 (13), 12.1600 (13)
α, β, γ (°)90.825 (2), 102.5614 (19), 95.142 (2)
V (Å3)1579.1 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.25
Crystal size (mm)0.49 × 0.31 × 0.29
Data collection
DiffractometerBruker APEX DUO CCD area-detector
Absorption correctionMulti-scan
(TWINABS; Bruker, 2009)
Tmin, Tmax0.711, 0.857
No. of measured, independent and
observed [I > 2σ(I)] reflections		5665, 5665, 5334
Rint?
(sin θ/λ)max (Å−1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.119, 1.10
No. of reflections5665
No. of parameters402
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.34, −0.35

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS2013 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

 

Acknowledgements

SS thanks the Alva's Education Foundation, Moodbidri, for the research facilities. The authors would like to thank the Universiti Malaysia Kelantan, SLAI from Malaysian Ministry of Higher Education and Universiti Sains Malaysia for the RU research Grant (Nos. PKIMIA/846017 and 1001/PKIMIA/811269) which partly supported this work.

References

First citationBruker (2009). APEX2, SAINT and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationSamshuddin, S., Narayana, B., Sarojini, B. K., Khan, M. T. H., Yathirajan, H. S., Raj, C. G. D. & Raghavendra, R. (2012). Med. Chem. Res. 21, 2012–2022.  Web of Science CSD CrossRef CAS Google Scholar
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 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWiley, R. H., Jarboe, C. H., Hayes, F. N., Hansbury, E., Nielsen, J. T., Callahan, P. X. & Sellars, M. C. (1958). J. Org. Chem. 23, 732–738.  CrossRef CAS Web of Science Google Scholar
 First citationZhi-Yun, L. U., Wei-Guo, Z. H. U., Qing, J. & Ming-Gui, X. I. E. (1999). Chin. Chem. Lett. 10, 679–682.  Google Scholar

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Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 1| January 2016| x152460
doi:10.1107/S2414314615024608
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