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

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ISSN: 2056-9890

4-(4-Chloro­phen­yl)-8-methyl-2-oxo-1,2,3,4,4a,5,6,7-octa­hydro­quinoline-3-carbo­nitrile

aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, bCenter of Excellence for Advanced Materials Research, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 5 September 2011; accepted 5 September 2011; online 14 September 2011)

The six-membered N-heterocyclic ring of title compound, C17H17ClN2O, is fused with a methyl-substituted cyclo­hexene ring. The nitro­gen-bearing ring has an envelope conformation with the benzene ring-bearing C atom lying 0.432 (6) Å out of the plane defined by the other five atoms (r.m.s. deviation 0.011 Å); its benzene substituent is aligned at 84.7 (1)° to the latter plane. The cyclo­hexene ring adopts a half-chair conformation. In the crystal, two mol­ecules are linked about a center of inversion by pairs of N–H⋯O hydrogen bonds, generating dimers. An ethyl­ene portion is disordered over two orientations in a 1:1 ratio. The crystal studied was a non-merohedral twin with a 15.3 (1)% minor component.

Related literature

For a similar compound that has two more H atoms, see: Asiri et al. (2011[Asiri, A. M., Al-Youbi, A. O., Faidallah, H. M., Badahdah, K. O. & Ng, S. W. (2011). Acta Cryst. E67, o2596.]).

[Scheme 1]

Experimental

Crystal data
  • C17H17ClN2O

  • Mr = 300.78

  • Monoclinic, P 21 /c

  • a = 11.0699 (7) Å

  • b = 7.6018 (3) Å

  • c = 18.2247 (9) Å

  • β = 100.505 (6)°

  • V = 1507.92 (13) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 2.24 mm−1

  • T = 100 K

  • 0.30 × 0.20 × 0.05 mm

Data collection
  • Agilent SuperNova Dual diffractometer with Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.554, Tmax = 0.896

  • 25955 measured reflections

  • 6143 independent reflections

  • 3143 reflections with I > 2σ(I)

  • Rint = 0.020

Refinement
  • R[F2 > 2σ(F2)] = 0.079

  • wR(F2) = 0.273

  • S = 1.10

  • 6140 reflections

  • 199 parameters

  • 18 restraints

  • H-atom parameters constrained

  • Δρmax = 0.68 e Å−3

  • Δρmin = −0.46 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O1i 0.88 2.07 2.923 (3) 162
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The compound (Scheme I) is a side product that was isolated along with 4-(4-chlorophenyl)-8-methyl-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3- carbonitrile, the expected product (Asiri et al., 2011); the proportion of the two compounds is unknown. The compound has one set of carbon-carbon double-bonds whereas the expected product has two, i.e., it has two more hydrogen atoms. Futhermore, the double-bond is now located in the methyl-substituted cyclohexene ring. The six-membered ring bearing an N atom that is fused with the cyclohexene ring. The nitrogen-bearing ring has the benzene-bearing C atom lying 0.432 (6) Å out of the plane defined by the other five atoms (r.m.s. deviation 0.011 Å); its benzene substituent is aligned at 84.7 (1) °. The cyclohexene ring adopts a half-chair conformation; an ethylene portion is disordered over two positions in a 1:1 ratio (Fig. 1). Two molecules are linked about a center-of-inversion by an N–H···O hydrogen bond to generate a dimer (Table 1).

Related literature top

For a similar compound that has two more H atoms, see: Asiri et al. (2011).

Experimental top

4-Chlorobenzaldehyde (1.4 g, 10 mmol), 2-methylcyclohexanone (1.2 g, 10 mmol), ethyl cyanoacetate (1.1 g, 10 mmol) and ammonium acetate (6.2 g, 80 mmol) were heated in ethanol (50 ml) for 6 h. The solid product was collected, washed with water and then recrystallized from ethanol.

One crystal was characterized as 4-(4-chlorophenyl)-8-methyl-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3- carbonitrile, the expected product (Asiri et al., 2011). The second type of crystal is not aromatic and it has two extra hydrogen atoms in the nitrogen-bearing ring (Scheme I).

Refinement top

Carbon- and nitrogen-bound H-atoms were placed in calculated positions [C–H 0.95–0.99 and N–H 0.88 Å; Uiso(H) 1.2–1.5 Ueq(C,N)] and were included in the refinement in the riding model approximation. The methyl group was treated as an idealized disordered group with the two positions rotated by 60°.

An ethylene section of the cyclohexene ring is disordered over two positions; the disorder could not be refined, and was regarded as a 1:1 type of disorder. Within the ring, the 1,2-related bond distances were restrained to 1.54±0.01 Å and the 1,3-related non-bonded distances to 2.51±0.01 Å. The temperature factors of the primed atoms were set to those of the umprimed ones; the anisotropic temperature factors were restrained to be nearly isotropic.

Omitted from the refinement owing to bad disagreement were (-2 1 0), (2 3 - 3) and (-4 1 1).

The somewhat large weighting scheme is attributed to the twinned nature of the crystal, and this is compounded by disorder. The minor component refined to 15.3 (1)%.

Structure description top

The compound (Scheme I) is a side product that was isolated along with 4-(4-chlorophenyl)-8-methyl-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3- carbonitrile, the expected product (Asiri et al., 2011); the proportion of the two compounds is unknown. The compound has one set of carbon-carbon double-bonds whereas the expected product has two, i.e., it has two more hydrogen atoms. Futhermore, the double-bond is now located in the methyl-substituted cyclohexene ring. The six-membered ring bearing an N atom that is fused with the cyclohexene ring. The nitrogen-bearing ring has the benzene-bearing C atom lying 0.432 (6) Å out of the plane defined by the other five atoms (r.m.s. deviation 0.011 Å); its benzene substituent is aligned at 84.7 (1) °. The cyclohexene ring adopts a half-chair conformation; an ethylene portion is disordered over two positions in a 1:1 ratio (Fig. 1). Two molecules are linked about a center-of-inversion by an N–H···O hydrogen bond to generate a dimer (Table 1).

For a similar compound that has two more H atoms, see: Asiri et al. (2011).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C17H17ClN2O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.
4-(4-Chlorophenyl)-8-methyl-2-oxo-1,2,3,4,4a,5,6,7- octahydroquinoline-3-carbonitrile top
Crystal data top
C17H17ClN2OF(000) = 632
Mr = 300.78Dx = 1.325 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybcCell parameters from 4615 reflections
a = 11.0699 (7) Åθ = 4.1–74.2°
b = 7.6018 (3) ŵ = 2.24 mm1
c = 18.2247 (9) ÅT = 100 K
β = 100.505 (6)°Prism, colorless
V = 1507.92 (13) Å30.30 × 0.20 × 0.05 mm
Z = 4
Data collection top
Agilent SuperNova Dual
diffractometer with Atlas detector
6143 independent reflections
Radiation source: SuperNova (Cu) X-ray Source3143 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.020
Detector resolution: 10.4041 pixels mm-1θmax = 74.6°, θmin = 4.1°
ω scanh = 1313
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
k = 89
Tmin = 0.554, Tmax = 0.896l = 2222
25955 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.079H-atom parameters constrained
wR(F2) = 0.273 w = 1/[σ2(Fo2) + (0.1311P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
6140 reflectionsΔρmax = 0.68 e Å3
199 parametersΔρmin = 0.46 e Å3
18 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0036 (12)
Crystal data top
C17H17ClN2OV = 1507.92 (13) Å3
Mr = 300.78Z = 4
Monoclinic, P21/cCu Kα radiation
a = 11.0699 (7) ŵ = 2.24 mm1
b = 7.6018 (3) ÅT = 100 K
c = 18.2247 (9) Å0.30 × 0.20 × 0.05 mm
β = 100.505 (6)°
Data collection top
Agilent SuperNova Dual
diffractometer with Atlas detector
6143 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
3143 reflections with I > 2σ(I)
Tmin = 0.554, Tmax = 0.896Rint = 0.020
25955 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.07918 restraints
wR(F2) = 0.273H-atom parameters constrained
S = 1.10Δρmax = 0.68 e Å3
6140 reflectionsΔρmin = 0.46 e Å3
199 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.94318 (9)0.09540 (11)0.08219 (4)0.0756 (3)
O10.5121 (3)0.5375 (4)0.41298 (14)0.1111 (12)
N10.6012 (3)0.2957 (3)0.47183 (14)0.0731 (8)
H10.56900.32340.51110.088*
N20.6458 (5)0.6373 (4)0.2684 (2)0.1182 (15)
C10.6727 (3)0.1423 (4)0.47779 (17)0.0667 (9)
C20.6849 (3)0.0426 (4)0.53982 (18)0.0724 (9)
C30.6222 (4)0.0736 (5)0.6033 (2)0.0845 (11)
H3A0.66090.00200.64590.127*0.50
H3B0.53540.04100.58920.127*0.50
H3C0.62860.19830.61710.127*0.50
H3D0.55570.15890.58890.127*0.50
H3E0.68120.11980.64560.127*0.50
H3F0.58800.03740.61770.127*0.50
C40.7734 (15)0.1120 (17)0.5423 (7)0.102 (3)0.50
H4A0.75160.20090.57740.123*0.50
H4B0.85730.06980.56280.123*0.50
C50.7757 (9)0.2041 (13)0.4660 (5)0.084 (3)0.50
H5A0.83530.30250.47100.101*0.50
H5B0.69340.24660.44200.101*0.50
C60.8189 (4)0.0437 (5)0.4237 (2)0.1017 (15)
H6A0.89610.00380.45310.122*0.50
H6B0.83640.08390.37500.122*0.50
H6C0.89990.01160.42360.122*0.50
H6D0.80250.12320.38000.122*0.50
C4'0.7531 (16)0.1306 (17)0.5520 (8)0.102 (3)0.50
H4'A0.69350.22840.54980.123*0.50
H4'B0.80610.13140.60200.123*0.50
C5'0.8316 (9)0.1565 (13)0.4924 (4)0.084 (3)0.50
H5'A0.91830.14730.51790.101*0.50
H5'B0.81900.27960.47490.101*0.50
C70.7272 (4)0.0954 (5)0.4112 (2)0.0914 (13)
H70.65680.02940.38130.110*
C80.7367 (3)0.2397 (4)0.36058 (16)0.0606 (7)
H80.80270.31360.39050.073*
C90.6351 (4)0.3604 (5)0.3464 (2)0.0936 (14)
H90.56980.29160.31340.112*
C100.5762 (4)0.4046 (5)0.41368 (19)0.0866 (12)
C110.6450 (4)0.5194 (4)0.30371 (18)0.0706 (9)
C120.7915 (3)0.1957 (3)0.29240 (15)0.0555 (7)
C130.7323 (3)0.0835 (4)0.23823 (16)0.0603 (7)
H130.65800.02850.24490.072*
C140.7794 (3)0.0495 (4)0.17398 (17)0.0645 (8)
H140.73820.02930.13730.077*
C150.8864 (3)0.1311 (4)0.16408 (16)0.0588 (7)
C160.9464 (4)0.2382 (5)0.2169 (2)0.0898 (12)
H161.02080.29240.21000.108*
C170.9001 (3)0.2709 (5)0.28208 (19)0.0845 (11)
H170.94400.34560.31950.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1037 (7)0.0772 (5)0.0564 (4)0.0074 (4)0.0422 (4)0.0022 (4)
O10.156 (3)0.115 (2)0.0785 (17)0.082 (2)0.0643 (18)0.0375 (15)
N10.0919 (19)0.0772 (17)0.0608 (14)0.0330 (15)0.0417 (14)0.0202 (13)
N20.222 (5)0.0612 (18)0.094 (2)0.028 (2)0.088 (3)0.0162 (17)
C10.073 (2)0.0755 (19)0.0606 (17)0.0233 (16)0.0353 (15)0.0164 (15)
C20.081 (2)0.076 (2)0.0669 (19)0.0181 (17)0.0324 (17)0.0249 (16)
C30.116 (3)0.082 (2)0.0614 (19)0.009 (2)0.031 (2)0.0071 (17)
C40.140 (5)0.105 (4)0.083 (4)0.046 (4)0.074 (4)0.058 (3)
C50.098 (6)0.087 (5)0.073 (5)0.043 (4)0.035 (4)0.032 (4)
C60.137 (4)0.097 (3)0.089 (3)0.064 (3)0.066 (3)0.042 (2)
C4'0.140 (5)0.105 (4)0.083 (4)0.046 (4)0.074 (4)0.058 (3)
C5'0.098 (6)0.087 (5)0.073 (5)0.043 (4)0.035 (4)0.032 (4)
C70.117 (3)0.095 (3)0.079 (2)0.050 (2)0.062 (2)0.039 (2)
C80.082 (2)0.0543 (15)0.0518 (14)0.0011 (15)0.0290 (15)0.0014 (12)
C90.138 (3)0.085 (2)0.074 (2)0.054 (2)0.061 (2)0.0329 (19)
C100.112 (3)0.090 (2)0.069 (2)0.051 (2)0.049 (2)0.0215 (18)
C110.112 (3)0.0497 (15)0.0594 (17)0.0056 (17)0.0401 (18)0.0032 (14)
C120.0720 (19)0.0486 (14)0.0511 (14)0.0042 (13)0.0253 (13)0.0023 (11)
C130.0702 (18)0.0533 (15)0.0645 (17)0.0016 (14)0.0308 (15)0.0010 (13)
C140.083 (2)0.0580 (17)0.0565 (16)0.0004 (15)0.0243 (16)0.0096 (13)
C150.0743 (19)0.0574 (16)0.0511 (15)0.0018 (14)0.0284 (14)0.0009 (12)
C160.099 (3)0.108 (3)0.075 (2)0.038 (2)0.049 (2)0.019 (2)
C170.093 (2)0.103 (3)0.0655 (19)0.038 (2)0.0371 (19)0.0272 (19)
Geometric parameters (Å, º) top
Cl1—C151.743 (3)C6—H6B0.9900
O1—C101.234 (4)C6—H6C0.9900
N1—C101.333 (4)C6—H6D0.9900
N1—C11.403 (4)C4'—C5'1.523 (9)
N1—H10.8800C4'—H4'A0.9900
N2—C111.104 (4)C4'—H4'B0.9900
C1—C21.347 (4)C5'—H5'A0.9900
C1—C71.494 (4)C5'—H5'B0.9900
C2—C31.474 (4)C7—C81.449 (4)
C2—C4'1.513 (8)C7—H71.0000
C2—C41.525 (8)C8—C91.438 (4)
C3—H3A0.9800C8—C121.516 (3)
C3—H3B0.9800C8—H81.0000
C3—H3C0.9800C9—C111.452 (4)
C3—H3D0.9800C9—C101.527 (4)
C3—H3E0.9800C9—H91.0000
C3—H3F0.9800C12—C171.375 (4)
C4—C51.560 (9)C12—C131.376 (4)
C4—H4A0.9900C13—C141.390 (4)
C4—H4B0.9900C13—H130.9500
C5—C61.564 (10)C14—C151.378 (4)
C5—H5A0.9900C14—H140.9500
C5—H5B0.9900C15—C161.341 (5)
C6—C71.455 (4)C16—C171.399 (4)
C6—C5'1.502 (6)C16—H160.9500
C6—H6A0.9900C17—H170.9500
C10—N1—C1127.6 (2)C2—C4'—H4'B109.7
C10—N1—H1116.2C5'—C4'—H4'B109.7
C1—N1—H1116.2H4'A—C4'—H4'B108.2
C2—C1—N1120.1 (3)C6—C5'—C4'122.8 (8)
C2—C1—C7123.6 (3)C6—C5'—H5'A106.6
N1—C1—C7116.2 (2)C4'—C5'—H5'A106.6
C1—C2—C3125.4 (3)C6—C5'—H5'B106.6
C1—C2—C4'125.7 (5)C4'—C5'—H5'B106.6
C3—C2—C4'108.5 (5)H5'A—C5'—H5'B106.6
C1—C2—C4115.1 (5)C8—C7—C6121.4 (3)
C3—C2—C4119.5 (5)C8—C7—C1115.0 (3)
C2—C3—H3A109.5C6—C7—C1114.8 (3)
C2—C3—H3B109.5C8—C7—H7100.0
H3A—C3—H3B109.5C6—C7—H7100.0
C2—C3—H3C109.5C1—C7—H7100.0
H3A—C3—H3C109.5C9—C8—C7116.9 (3)
H3B—C3—H3C109.5C9—C8—C12114.2 (3)
C2—C3—H3D109.5C7—C8—C12116.1 (2)
C2—C3—H3E109.5C9—C8—H8102.1
H3D—C3—H3E109.5C7—C8—H8102.1
C2—C3—H3F109.5C12—C8—H8102.1
H3D—C3—H3F109.5C8—C9—C11119.6 (3)
H3E—C3—H3F109.5C8—C9—C10115.5 (3)
C2—C4—C5115.8 (9)C11—C9—C10109.4 (3)
C2—C4—H4A108.3C8—C9—H9103.3
C5—C4—H4A108.3C11—C9—H9103.3
C2—C4—H4B108.3C10—C9—H9103.3
C5—C4—H4B108.3O1—C10—N1123.5 (3)
H4A—C4—H4B107.4O1—C10—C9120.1 (3)
C6—C5—C498.4 (8)N1—C10—C9116.4 (3)
C6—C5—H5A112.1N2—C11—C9175.5 (5)
C4—C5—H5A112.1C17—C12—C13118.2 (3)
C6—C5—H5B112.1C17—C12—C8120.7 (3)
C4—C5—H5B112.1C13—C12—C8121.0 (3)
H5A—C5—H5B109.7C12—C13—C14121.1 (3)
C7—C6—C5'120.1 (5)C12—C13—H13119.4
C7—C6—C5112.1 (5)C14—C13—H13119.4
C7—C6—H6A109.2C15—C14—C13119.3 (3)
C5—C6—H6A109.2C15—C14—H14120.3
C7—C6—H6B109.2C13—C14—H14120.3
C5—C6—H6B109.2C16—C15—C14120.3 (3)
H6A—C6—H6B107.9C16—C15—Cl1120.0 (2)
C7—C6—H6C107.3C14—C15—Cl1119.7 (2)
C5'—C6—H6C107.3C15—C16—C17120.5 (3)
C7—C6—H6D107.3C15—C16—H16119.8
C5'—C6—H6D107.3C17—C16—H16119.8
H6C—C6—H6D106.9C12—C17—C16120.4 (3)
C2—C4'—C5'109.9 (9)C12—C17—H17119.8
C2—C4'—H4'A109.7C16—C17—H17119.8
C5'—C4'—H4'A109.7
C10—N1—C1—C2177.3 (4)C6—C7—C8—C9173.9 (4)
C10—N1—C1—C70.0 (6)C1—C7—C8—C940.3 (6)
N1—C1—C2—C34.0 (6)C6—C7—C8—C1234.3 (6)
C7—C1—C2—C3173.1 (4)C1—C7—C8—C12179.9 (3)
N1—C1—C2—C4'176.4 (10)C7—C8—C9—C11172.5 (4)
C7—C1—C2—C4'0.6 (12)C12—C8—C9—C1147.2 (5)
N1—C1—C2—C4175.1 (8)C7—C8—C9—C1038.5 (6)
C7—C1—C2—C47.8 (10)C12—C8—C9—C10178.8 (3)
C1—C2—C4—C535.6 (14)C1—N1—C10—O1180.0 (4)
C3—C2—C4—C5145.3 (8)C1—N1—C10—C91.9 (6)
C4'—C2—C4—C5112 (6)C8—C9—C10—O1161.0 (4)
C2—C4—C5—C661.4 (12)C11—C9—C10—O122.5 (6)
C4—C5—C6—C766.5 (8)C8—C9—C10—N117.2 (6)
C4—C5—C6—C5'45.8 (11)C11—C9—C10—N1155.6 (4)
C1—C2—C4'—C5'13.3 (18)C9—C8—C12—C17102.9 (4)
C3—C2—C4'—C5'173.2 (10)C7—C8—C12—C17116.5 (4)
C4—C2—C4'—C5'23 (5)C9—C8—C12—C1375.2 (4)
C7—C6—C5'—C4'1.2 (15)C7—C8—C12—C1365.4 (4)
C5—C6—C5'—C4'83.5 (18)C17—C12—C13—C141.2 (5)
C2—C4'—C5'—C612.1 (19)C8—C12—C13—C14176.9 (3)
C5'—C6—C7—C8160.1 (6)C12—C13—C14—C150.8 (5)
C5—C6—C7—C8167.6 (5)C13—C14—C15—C162.0 (5)
C5'—C6—C7—C114.2 (8)C13—C14—C15—Cl1177.7 (2)
C5—C6—C7—C146.6 (7)C14—C15—C16—C171.1 (6)
C2—C1—C7—C8162.0 (4)Cl1—C15—C16—C17178.6 (3)
N1—C1—C7—C820.8 (5)C13—C12—C17—C162.1 (6)
C2—C1—C7—C614.0 (6)C8—C12—C17—C16176.0 (4)
N1—C1—C7—C6168.9 (4)C15—C16—C17—C121.0 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.882.072.923 (3)162
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC17H17ClN2O
Mr300.78
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)11.0699 (7), 7.6018 (3), 18.2247 (9)
β (°) 100.505 (6)
V3)1507.92 (13)
Z4
Radiation typeCu Kα
µ (mm1)2.24
Crystal size (mm)0.30 × 0.20 × 0.05
Data collection
DiffractometerAgilent SuperNova Dual
diffractometer with Atlas detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2010)
Tmin, Tmax0.554, 0.896
No. of measured, independent and
observed [I > 2σ(I)] reflections
25955, 6143, 3143
Rint0.020
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.079, 0.273, 1.10
No. of reflections6140
No. of parameters199
No. of restraints18
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.68, 0.46

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.882.072.923 (3)162
Symmetry code: (i) x+1, y+1, z+1.
 

Acknowledgements

We thank King Abdulaziz University and the University of Malaya for supporting this study.

References

First citationAgilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.  Google Scholar
First citationAsiri, A. M., Al-Youbi, A. O., Faidallah, H. M., Badahdah, K. O. & Ng, S. W. (2011). Acta Cryst. E67, o2596.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  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

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