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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(Z)-Iso­butyl 2-benzamido-3-(4-chloro­phen­yl)acrylate

aCollege of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin 541004, People's Republic of China
*Correspondence e-mail: edward_su75@163.com

(Received 5 October 2009; accepted 23 October 2009; online 28 October 2009)

The title compound, C20H20ClNO3, is a α-amino acid derivative which displays a Z configuration about the C=C double bond. The dihedral angle betwen the aromatic rings is 87.75 (12)°. The mol­ecular conformation is stabilized by an intra­molecular C—H⋯N hydrogen bond. In the crystal structure, centrosymmetrically related mol­ecules inter­act through inter­molecular C—H⋯O hydrogen-bond inter­actions, forming dimers. The dimers are further linked into chains parallel to the a axis by N—H⋯O hydrogen bonds. The methyl groups of the isopropyl group are disordered over two positions with occupancy factors of 0.5.

Related literature

For the synthesis and crystal structure of related compounds, see: Jiménez et al. (2000[Jiménez, A. I., Cativiela, C., Gómez-Catalán, J., Pérez, J. J. & Aubry, A. C. (2000). J. Am. Chem. Soc. 122, 5811-5821.]); Peggion et al. (2003[Peggion, C., Formaggio, F., Crisma, M., Toniolo, C., Jiménez, A. I., Cativiela, C., Kaptein, B., Broxterman, Q. B., Saviano, M. & Benedetti, E. (2003). Biopolymers, 68, 178-191.]).

[Scheme 1]

Experimental

Crystal data
  • C20H20ClNO3

  • Mr = 357.82

  • Triclinic, [P \overline 1]

  • a = 5.0179 (10) Å

  • b = 12.581 (2) Å

  • c = 16.293 (3) Å

  • α = 67.623 (11)°

  • β = 83.991 (15)°

  • γ = 79.548 (14)°

  • V = 934.6 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 293 K

  • 0.50 × 0.40 × 0.25 mm

Data collection
  • Rigaku AFC-7S Mercury diffractometer

  • Absorption correction: multi-scan (REQAB; Jacobson, 1998[Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.897, Tmax = 0.946

  • 9082 measured reflections

  • 3380 independent reflections

  • 2224 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.073

  • wR(F2) = 0.213

  • S = 1.10

  • 3380 reflections

  • 231 parameters

  • 5 restraints

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

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3⋯O1i 0.93 2.43 3.299 (4) 155
N1—H1⋯O3ii 0.86 2.07 2.916 (3) 169
C9—H9⋯N1 0.93 2.55 3.103 (4) 119
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x+1, y, z.

Data collection: CrystalClear (Rigaku/MSC, 2000[Rigaku/MSC (2000). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004[Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); 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.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

As part of a study on the effect of the conformationally restricted molecular substitution on the crystal structures of biologically important class of compounds, we report herein the crystal structure of the title compound. Small and medium α-amino acids are generally highly flexible molecules that exist in solution in a dynamic equilibrium of interchanging conformations. As a consequence, most natural α-amino acids with physiological activity cannot be used for therapeutic purposes so we developed the introduction of conformational constrains. In comparison with native α-amino acids, side chain restricted analogues usually display more favorable pharmacological properties (Jiménez et al., 2000; Peggion et al., 2003).

The molecule of the title compound (Fig. 1) displays a Z configuration about the C2C3 double bond. The molecular conformation is enforced by an intramolecular C—H···N hydrogen bond (Table 1). The C19 and C20 methyl groups of the isopropyl group are disordered over two positions with occupancy factors of 0.5. The dihedral angle formed by the aromatic rings is 87.75 (12)°. In the crystal packing, centrosymmetrically related molecules are linked into dimers by intermolecular C—H···O hydrogen bonds. The dimers are further connected by N—H···O hydrogen bonds to form chains parallel to the a axis (Fig. 2).

Related literature top

For the synthesis and crystal structure of related compounds, see: Jiménez et al. (2000); Peggion et al. (2003).

Experimental top

Compound B (Fig. 3): to a 100 ml round-bottomed flask was added 1.4 g (1.18 ml, 0.01 mol) of redistilled 4-chlorobenzaldehyde, 1.79 g (0.01 mol) of benzoylglycine, 3.1 g (2.8 ml, 0.03 mol) of acetic anhydride and 0.82 g (0.01 mol) of anhydrous sodium acetate, and the mixture was heated on an electric hotplace with constant shaking. Once liquefied completely, the round-bottomed flask was transferred to a water bath and heated at 100 °C for 2 h, then 16 ml of ethanol was added slowly to the flask and the mixture allowed to stand overnight. The crystalline product was filtered with suction, washed twice with 25 ml of ice-cold alcohol and twice with 25 ml of boiling water and dried to afford 1.91 g of pure compound B (yield 64%).

Compound C (Fig. 3): to a 0.1% solution of sodium methoxide in absolute methanol (40 ml) was added 2.1 g of compound B (3.52 mmol). The mixture was heated to 75 °C under vigorously stirring until TLC analysis indicated that the starting material had disappeared (about 2 h). The product was collected by vacuum filtration and washed with small portions of cold methanol to afford 2.16 g of compound C as a white solid (yield 92%).

Title compound (D, Fig. 3): to a 100 ml round-bottomed flask was added 0.303 g (1.0 mmol) of compound C, 9.9 g (10 ml, 0.13 mol) of redistilled isobutanol, 10 ml of redistilled cyclohexane and 2 ml of concentrated sulfuric acid under stirring. The mixture was refluxed 4 h with stirring, then cooled and the product extracted with chloroform (2× 15 ml). The combined organic layer was dried over MgSO4, filtered and the solvent removed under reduced pressure to afford 0.293 g of the title compound as a white solid (yield 81%). Crystals suitable for X-ray analysis were obtained by slow evaporation of a dichloromethane-ethanol solution (1:2 v/v). IR 3837, 3745, 3648, 3165, 1737. 1H NMR (DMSO-d6, 500 MHz) δ 0.85 (d, 6H, J=6.75 Hz); 1.86 (m, 1H); 3.91 (d, 2H, J=6.4 Hz); 7.38 (s, 1H); 7.46 (d, 2H, J=8.5 Hz); 7.49–7.53 (m, 2H); 7.57–7.59 (m, 1H); 7.68 (d, 2H, J=8.5 Hz); 7.93 (d, 2H, J=7.1 Hz); 10.0 (s, 1H). 13C NMR (DMSO-d6, 125.8 MHz) δ 18.7, 27.2, 70.7, 127.4, 127.5, 128.4, 128.6, 131.3, 131.6, 131.8, 132.3, 133.2, 133.9, 164.8, 166.4.

Refinement top

The H atom on C18 was located in a difference Fourier map and refined isotropically. Other H atom were positioned geometrically and included in the refinement in the riding-model approximation, with C—H = 0.93–0.97 Å, N—H = 0.86 Å, and with Uĩso~(H) = 1.5U~eq~(C, N). The methyl groups C19 and C20 of the isopropyl group are disordered over two positions with occupancy factors of 0.5 and were refined isotropically. The C—C distances within the isopropyl group were restrained to be 1.54 (1) Å.

Structure description top

As part of a study on the effect of the conformationally restricted molecular substitution on the crystal structures of biologically important class of compounds, we report herein the crystal structure of the title compound. Small and medium α-amino acids are generally highly flexible molecules that exist in solution in a dynamic equilibrium of interchanging conformations. As a consequence, most natural α-amino acids with physiological activity cannot be used for therapeutic purposes so we developed the introduction of conformational constrains. In comparison with native α-amino acids, side chain restricted analogues usually display more favorable pharmacological properties (Jiménez et al., 2000; Peggion et al., 2003).

The molecule of the title compound (Fig. 1) displays a Z configuration about the C2C3 double bond. The molecular conformation is enforced by an intramolecular C—H···N hydrogen bond (Table 1). The C19 and C20 methyl groups of the isopropyl group are disordered over two positions with occupancy factors of 0.5. The dihedral angle formed by the aromatic rings is 87.75 (12)°. In the crystal packing, centrosymmetrically related molecules are linked into dimers by intermolecular C—H···O hydrogen bonds. The dimers are further connected by N—H···O hydrogen bonds to form chains parallel to the a axis (Fig. 2).

For the synthesis and crystal structure of related compounds, see: Jiménez et al. (2000); Peggion et al. (2003).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2000); cell refinement: CrystalClear (Rigaku/MSC, 2000); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 20% probability displacement ellipsoids.
[Figure 2] Fig. 2. Partial packing diagram of the title compound showing the formation of chains parallel to the a axis. Intermolecular hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding are omitted for clarity.
[Figure 3] Fig. 3. Synthesis of the title compound.
(Z)-Isobutyl 2-benzamido-3-(4-chlorophenyl)acrylate top
Crystal data top
C20H20ClNO3Z = 2
Mr = 357.82F(000) = 376
Triclinic, P1Dx = 1.271 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71070 Å
a = 5.0179 (10) ÅCell parameters from 2536 reflections
b = 12.581 (2) Åθ = 3.3–25.3°
c = 16.293 (3) ŵ = 0.22 mm1
α = 67.623 (11)°T = 293 K
β = 83.991 (15)°Block, colourless
γ = 79.548 (14)°0.50 × 0.40 × 0.25 mm
V = 934.6 (3) Å3
Data collection top
Rigaku AFC-7S Mercury
diffractometer
3380 independent reflections
Radiation source: fine-focus sealed tube2224 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 7.31 pixels mm-1θmax = 25.4°, θmin = 3.3°
ω scansh = 65
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)
k = 1515
Tmin = 0.897, Tmax = 0.946l = 1919
9082 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)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.213H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0999P)2 + 0.2158P]
where P = (Fo2 + 2Fc2)/3
3380 reflections(Δ/σ)max < 0.001
231 parametersΔρmax = 0.40 e Å3
5 restraintsΔρmin = 0.37 e Å3
Crystal data top
C20H20ClNO3γ = 79.548 (14)°
Mr = 357.82V = 934.6 (3) Å3
Triclinic, P1Z = 2
a = 5.0179 (10) ÅMo Kα radiation
b = 12.581 (2) ŵ = 0.22 mm1
c = 16.293 (3) ÅT = 293 K
α = 67.623 (11)°0.50 × 0.40 × 0.25 mm
β = 83.991 (15)°
Data collection top
Rigaku AFC-7S Mercury
diffractometer
3380 independent reflections
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)
2224 reflections with I > 2σ(I)
Tmin = 0.897, Tmax = 0.946Rint = 0.036
9082 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0735 restraints
wR(F2) = 0.213H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.40 e Å3
3380 reflectionsΔρmin = 0.37 e Å3
231 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. 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 > σ(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*/UeqOcc. (<1)
Cl11.2590 (3)0.91744 (12)0.10142 (11)0.1191 (6)
O10.3603 (6)0.3847 (3)0.09779 (16)0.0827 (9)
O20.4837 (5)0.2561 (2)0.23066 (16)0.0671 (7)
O30.2050 (4)0.4200 (2)0.31239 (15)0.0632 (7)
N10.6503 (5)0.4156 (2)0.27693 (15)0.0447 (7)
H10.80970.40990.29460.054*
C10.4725 (7)0.3599 (3)0.1656 (2)0.0535 (9)
C20.6145 (6)0.4408 (3)0.18535 (19)0.0469 (8)
C30.7106 (7)0.5258 (3)0.1182 (2)0.0512 (8)
H30.68480.52670.06220.061*
C40.8503 (7)0.6182 (3)0.1178 (2)0.0502 (8)
C51.0086 (9)0.6722 (4)0.0447 (2)0.0761 (12)
H51.02960.64660.00250.091*
C61.1369 (10)0.7627 (4)0.0391 (3)0.0880 (14)
H61.24500.79680.01070.106*
C71.1039 (8)0.8020 (3)0.1076 (3)0.0712 (11)
C80.9483 (10)0.7509 (4)0.1812 (3)0.0811 (13)
H80.92750.77750.22790.097*
C90.8221 (9)0.6602 (3)0.1863 (2)0.0709 (11)
H90.71570.62610.23660.085*
C100.4399 (6)0.4007 (3)0.33605 (19)0.0448 (8)
C110.5016 (6)0.3597 (3)0.43160 (19)0.0476 (8)
C120.7329 (8)0.2865 (3)0.4664 (2)0.0645 (10)
H120.86420.26230.42980.077*
C130.7701 (10)0.2483 (4)0.5579 (3)0.0851 (14)
H130.92600.19810.58250.102*
C140.5761 (11)0.2853 (5)0.6111 (3)0.0839 (14)
H140.60080.25950.67180.101*
C150.3528 (11)0.3577 (5)0.5768 (3)0.0859 (13)
H150.22450.38340.61330.103*
C160.3112 (8)0.3944 (4)0.4881 (2)0.0680 (11)
H160.15230.44360.46520.082*
C170.3195 (10)0.1773 (4)0.2212 (3)0.0856 (14)
H17A0.35500.17210.16310.103*
H17B0.12850.20630.22680.103*
C180.3886 (8)0.0619 (4)0.2908 (3)0.0781 (12)
H180.275 (6)0.012 (3)0.281 (2)0.073 (11)*
C190.669 (2)0.0005 (11)0.3151 (8)0.107 (2)*0.50
H19A0.76280.04720.33360.160*0.50
H19B0.76380.01220.26460.160*0.50
H19C0.66030.07290.36290.160*0.50
C19'0.662 (2)0.0186 (11)0.2528 (8)0.107 (2)*0.50
H19D0.79840.05990.25790.160*0.50
H19E0.64500.03200.19130.160*0.50
H19F0.71260.06320.28530.160*0.50
C200.262 (2)0.0812 (11)0.3758 (7)0.101 (2)*0.50
H20A0.24810.00730.42240.152*0.50
H20B0.08470.12640.36380.152*0.50
H20C0.37480.12180.39370.152*0.50
C20'0.422 (2)0.0469 (11)0.3842 (7)0.101 (2)*0.50
H20D0.47010.03420.41910.152*0.50
H20E0.25460.07700.40760.152*0.50
H20F0.56250.08830.38620.152*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1242 (12)0.0830 (9)0.1589 (14)0.0548 (8)0.0204 (10)0.0333 (9)
O10.116 (2)0.088 (2)0.0517 (14)0.0472 (18)0.0216 (15)0.0154 (14)
O20.0817 (18)0.0547 (16)0.0676 (15)0.0262 (13)0.0179 (13)0.0148 (13)
O30.0374 (13)0.0924 (19)0.0553 (13)0.0180 (12)0.0059 (10)0.0178 (13)
N10.0384 (13)0.0568 (17)0.0390 (13)0.0168 (12)0.0038 (11)0.0129 (12)
C10.057 (2)0.059 (2)0.0469 (18)0.0184 (17)0.0037 (16)0.0170 (17)
C20.0462 (18)0.056 (2)0.0393 (16)0.0155 (15)0.0004 (13)0.0148 (15)
C30.057 (2)0.059 (2)0.0412 (16)0.0174 (17)0.0015 (14)0.0190 (16)
C40.0516 (19)0.052 (2)0.0432 (16)0.0101 (16)0.0044 (14)0.0117 (15)
C50.095 (3)0.078 (3)0.059 (2)0.039 (2)0.018 (2)0.024 (2)
C60.096 (3)0.086 (3)0.084 (3)0.051 (3)0.024 (2)0.025 (3)
C70.066 (2)0.056 (2)0.090 (3)0.018 (2)0.016 (2)0.017 (2)
C80.117 (4)0.062 (3)0.072 (3)0.030 (3)0.012 (3)0.024 (2)
C90.098 (3)0.063 (2)0.056 (2)0.034 (2)0.005 (2)0.0187 (18)
C100.0439 (18)0.0495 (19)0.0404 (16)0.0147 (15)0.0017 (14)0.0124 (14)
C110.0487 (19)0.051 (2)0.0432 (16)0.0219 (16)0.0031 (15)0.0103 (15)
C120.061 (2)0.069 (3)0.0494 (18)0.0140 (19)0.0051 (17)0.0045 (18)
C130.082 (3)0.087 (3)0.066 (2)0.024 (3)0.027 (2)0.004 (2)
C140.105 (4)0.103 (4)0.047 (2)0.054 (3)0.002 (2)0.016 (2)
C150.105 (4)0.103 (4)0.055 (2)0.029 (3)0.004 (2)0.031 (2)
C160.069 (2)0.085 (3)0.053 (2)0.015 (2)0.0020 (18)0.028 (2)
C170.104 (3)0.068 (3)0.092 (3)0.044 (3)0.022 (3)0.019 (2)
C180.067 (3)0.060 (3)0.112 (3)0.020 (2)0.014 (2)0.029 (2)
Geometric parameters (Å, º) top
Cl1—C71.734 (4)C13—C141.371 (7)
O1—C11.200 (4)C13—H130.9300
O2—C11.328 (4)C14—C151.331 (7)
O2—C171.458 (4)C14—H140.9300
O3—C101.232 (4)C15—C161.365 (5)
N1—C101.341 (4)C15—H150.9300
N1—C21.426 (4)C16—H160.9300
N1—H10.8600C17—C181.470 (6)
C1—C21.485 (5)C17—H17A0.9700
C2—C31.327 (4)C17—H17B0.9700
C3—C41.459 (5)C18—C20'1.483 (10)
C3—H30.9300C18—C191.490 (10)
C4—C51.375 (5)C18—C19'1.540 (11)
C4—C91.390 (5)C18—C201.546 (10)
C5—C61.377 (6)C18—H180.99 (3)
C5—H50.9300C19—H19A0.9600
C6—C71.367 (6)C19—H19B0.9600
C6—H60.9300C19—H19C0.9600
C7—C81.363 (6)C19'—H19D0.9600
C8—C91.375 (5)C19'—H19E0.9600
C8—H80.9300C19'—H19F0.9600
C9—H90.9300C20—H20A0.9600
C10—C111.489 (4)C20—H20B0.9600
C11—C121.367 (5)C20—H20C0.9600
C11—C161.386 (5)C20'—H20D0.9600
C12—C131.404 (5)C20'—H20E0.9600
C12—H120.9300C20'—H20F0.9600
C1—O2—C17116.2 (3)C13—C14—H14119.7
C10—N1—C2121.2 (2)C14—C15—C16120.3 (4)
C10—N1—H1119.4C14—C15—H15119.8
C2—N1—H1119.4C16—C15—H15119.8
O1—C1—O2123.0 (3)C15—C16—C11121.1 (4)
O1—C1—C2123.9 (3)C15—C16—H16119.4
O2—C1—C2113.1 (3)C11—C16—H16119.4
C3—C2—N1124.9 (3)O2—C17—C18108.7 (3)
C3—C2—C1118.8 (3)O2—C17—H17A110.0
N1—C2—C1116.2 (3)C18—C17—H17A110.0
C2—C3—C4130.6 (3)O2—C17—H17B110.0
C2—C3—H3114.7C18—C17—H17B110.0
C4—C3—H3114.7H17A—C17—H17B108.3
C5—C4—C9116.9 (3)C17—C18—C20'122.0 (6)
C5—C4—C3119.6 (3)C17—C18—C19125.4 (6)
C9—C4—C3123.4 (3)C20'—C18—C1972.4 (7)
C4—C5—C6122.2 (4)C17—C18—C19'100.6 (6)
C4—C5—H5118.9C20'—C18—C19'108.9 (7)
C6—C5—H5118.9C17—C18—C20102.6 (6)
C7—C6—C5119.3 (4)C19—C18—C20104.4 (7)
C7—C6—H6120.3C19'—C18—C20140.7 (7)
C5—C6—H6120.3C17—C18—H18105 (2)
C8—C7—C6120.3 (4)C20'—C18—H18117 (2)
C8—C7—Cl1119.5 (3)C19—C18—H18112 (2)
C6—C7—Cl1120.2 (3)C19'—C18—H1899 (2)
C7—C8—C9119.9 (4)C20—C18—H18105 (2)
C7—C8—H8120.0C18—C19—H19A109.5
C9—C8—H8120.0C18—C19—H19B109.5
C8—C9—C4121.4 (4)C18—C19—H19C109.5
C8—C9—H9119.3C18—C19'—H19D109.5
C4—C9—H9119.3C18—C19'—H19E109.5
O3—C10—N1121.4 (3)H19D—C19'—H19E109.5
O3—C10—C11121.2 (3)C18—C19'—H19F109.5
N1—C10—C11117.3 (3)H19D—C19'—H19F109.5
C12—C11—C16118.7 (3)H19E—C19'—H19F109.5
C12—C11—C10123.0 (3)C18—C20—H20A109.5
C16—C11—C10118.3 (3)C18—C20—H20B109.5
C11—C12—C13119.3 (4)C18—C20—H20C109.5
C11—C12—H12120.4C18—C20'—H20D109.5
C13—C12—H12120.4C18—C20'—H20E109.5
C14—C13—C12119.9 (4)H20D—C20'—H20E109.5
C14—C13—H13120.1C18—C20'—H20F109.5
C12—C13—H13120.1H20D—C20'—H20F109.5
C15—C14—C13120.6 (4)H20E—C20'—H20F109.5
C15—C14—H14119.7
C17—O2—C1—O18.2 (5)C3—C4—C9—C8177.0 (4)
C17—O2—C1—C2172.3 (3)C2—N1—C10—O37.7 (5)
C10—N1—C2—C3130.9 (4)C2—N1—C10—C11172.3 (3)
C10—N1—C2—C152.9 (4)O3—C10—C11—C12147.3 (4)
O1—C1—C2—C325.4 (5)N1—C10—C11—C1232.7 (5)
O2—C1—C2—C3154.1 (3)O3—C10—C11—C1630.4 (5)
O1—C1—C2—N1158.2 (3)N1—C10—C11—C16149.6 (3)
O2—C1—C2—N122.3 (4)C16—C11—C12—C130.3 (5)
N1—C2—C3—C45.6 (6)C10—C11—C12—C13177.4 (3)
C1—C2—C3—C4178.3 (3)C11—C12—C13—C140.5 (6)
C2—C3—C4—C5158.4 (4)C12—C13—C14—C150.4 (7)
C2—C3—C4—C925.0 (6)C13—C14—C15—C161.3 (7)
C9—C4—C5—C60.7 (6)C14—C15—C16—C111.5 (7)
C3—C4—C5—C6177.5 (4)C12—C11—C16—C150.6 (6)
C4—C5—C6—C71.0 (7)C10—C11—C16—C15178.5 (3)
C5—C6—C7—C80.8 (7)C1—O2—C17—C18171.3 (3)
C5—C6—C7—Cl1178.9 (4)O2—C17—C18—C20'43.9 (8)
C6—C7—C8—C90.5 (7)O2—C17—C18—C1946.5 (8)
Cl1—C7—C8—C9179.3 (3)O2—C17—C18—C19'76.4 (6)
C7—C8—C9—C40.3 (7)O2—C17—C18—C2071.7 (6)
C5—C4—C9—C80.4 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O1i0.932.433.299 (4)155
N1—H1···O3ii0.862.072.916 (3)169
C9—H9···N10.932.553.103 (4)119
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC20H20ClNO3
Mr357.82
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)5.0179 (10), 12.581 (2), 16.293 (3)
α, β, γ (°)67.623 (11), 83.991 (15), 79.548 (14)
V3)934.6 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.50 × 0.40 × 0.25
Data collection
DiffractometerRigaku AFC-7S Mercury
Absorption correctionMulti-scan
(REQAB; Jacobson, 1998)
Tmin, Tmax0.897, 0.946
No. of measured, independent and
observed [I > 2σ(I)] reflections
9082, 3380, 2224
Rint0.036
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.073, 0.213, 1.10
No. of reflections3380
No. of parameters231
No. of restraints5
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.40, 0.37

Computer programs: CrystalClear (Rigaku/MSC, 2000), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O1i0.932.433.299 (4)155.2
N1—H1···O3ii0.862.072.916 (3)168.8
C9—H9···N10.932.553.103 (4)118.6
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z.
 

Acknowledgements

The authors thank the Natural Science Foundation of Guangxi Zhuang Autonomous Region (grant No. 0731054)

References

First citationJacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationJiménez, A. I., Cativiela, C., Gómez-Catalán, J., Pérez, J. J. & Aubry, A. C. (2000). J. Am. Chem. Soc. 122, 5811–5821.  Google Scholar
First citationPeggion, C., Formaggio, F., Crisma, M., Toniolo, C., Jiménez, A. I., Cativiela, C., Kaptein, B., Broxterman, Q. B., Saviano, M. & Benedetti, E. (2003). Biopolymers, 68, 178–191.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationRigaku/MSC (2000). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
First citationRigaku/MSC (2004). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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