(Z)-3-Chloro-3-phenyl-N-[(S)-1-phenyl­ethyl]prop-2-enamide

Urdaneta, N.A.; González, T.; Briceño, A.

doi:10.1107/S160053680801876X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1372

doi:10.1107/S160053680801876X

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(Z)-3-Chloro-3-phenyl-N-[(S)-1-phenylethyl]prop-2-enamide

Neudo A. Urdaneta,^a ^* Teresa González ^b and Alexander Briceño ^b ^*

^aLaboratorio de Organica 210, Departamento de Química, Universidad Simon Bolivar, Apartado 47206, Caracas 1080-A, Venezuela, and ^bCentro de Química, Instituto Venezolano de Investigaciones Científica (IVIC), Apartado 21827, Caracas 1020-A, Venezuela
^*Correspondence e-mail: urdaneta@usb.ve, abriceno@ivic.ve

(Received 13 June 2008; accepted 20 June 2008; online 5 July 2008)

The asymmetric unit of the title compound, C₁₇H₁₆ClNO, contains two crystallographically independent molecules. These molecules are connected in an alternating fashion through N—H⋯O and C—H⋯O hydrogen bonds, generating one-dimensional chains of graph sets R₂¹(6) and C(4) along the a axis.

Related literature

For related literature, see: Kishikawa et al., (1997 ); Cherry et al. (2003 ); Pontiki & Hadjipavlou (2007 ); Urdaneta et al. (2004 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₇H₁₆ClNO
M_r = 285.76
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.803 (3) Å
b = 14.976 (5) Å
c = 20.823 (6) Å
V = 3057.2 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 (2) K
0.48 × 0.38 × 0.28 mm

Data collection

Rigaku AFC-7S Mercury diffractometer
Absorption correction: multi-scan (Jacobson, 1998 ) T_min = 0.897, T_max = 0.985 (expected range = 0.850–0.934)
32660 measured reflections
5802 independent reflections
3687 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.161
S = 1.07
5802 reflections
362 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ), 1693 Friedel pairs
Flack parameter: −0.03 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.97	1.89	2.852 (4)	174
N2—H2N⋯O1	0.95	2.04	2.933 (5)	157
C10—H10⋯Cl1	0.93	2.64	3.021 (6)	105
C13—H13⋯N1	0.93	2.55	2.874 (5)	101
C19—H19⋯O1	0.93	2.50	3.315 (5)	146
C27—H27⋯Cl2	0.93	2.65	3.028 (6)	105
C30—H30⋯N2	0.93	2.65	2.951 (5)	99
Symmetry code: (i) x-1, y, z.

Data collection: CrystalClear (Rigaku, 2002 ); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL-NT and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801876X/hb2746sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680801876X/hb2746Isup2.hkl

checkCIF report

Comment top

The title compound, (I), represents a valuable intermediate for the synthesis of biologically active disubstituted pyrimidones (Cherry et al., 2003), phenyl-substituted amides with antioxidant and anti-inflamatory activity as novel lipoxygenase inhibitor (Pontiki & Hadjipavlou, 2007), and also as precursor for photochemical studies (Kishikawa et al., 1997).

The asymmetric unit of (I) contains two crystallographically indepedent molecules of the same stereochemical configuration (Fig. 1): C4 and C21 have S configuration. Each molecule displays two kinds of intramolecular C—H···Cl and C—H···N hydrogen bonds (Table 1). These interactions lead to the formation of five-membered rings described by graph-set symbol S(5) (Bernstein et al., 1995). In each molecule the phenyl groups are twisted with respect to the aliphatic chain defined by C4/N1/C3/O1/C2/C1 (CH1) and C21/N2/C18/C19/C20/O2 atoms (CH2), respectively. The dihedral angles between the C5—C10 and C12—C17 rings and the mean plane of the CH1 are 31.8 (2)° and 88.6 (2)°, for the molecule 1; C29—C34: 81.8 (2)° and C22—C2: 33.8 (2)° for the rings of the molecule 2. These molecules form a dimer linked through a N—H···O and C—H···O intermolecular hydrogen bonds in which the O atom from carbonyl group acts as a double aceptor of hydrogen bonds (Fig 1). This interaction produces a supramolecular motif described by the symbol R₂¹(6). These dimers are connected in an alternate fashion via remaining N—H···O intermolecular hydrogen bonds, generating one-dimensional chains along the a axis (Fig. 2), this interaction is described by the symbol C(4). Adjacent chains are assembled through C—H···π interactions to afford a three-dimensional array.

Related literature top

For related literature, see: Kishikawa et al., (1997); Cherry et al. (2003); Pontiki & Hadjipavlou (2007); Urdaneta et al. (2004). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

The title compound was prepared according to a reported procedure (Urdaneta et al., 2004), and colourless blocks of (I) were grown from a saturated AcOEt/Et₂O (1:9) solution kept at 277 K.

Computing details top

Data collection: CrystalClear (Rigaku, 2002); cell refinement: CrystalClear (Rigaku, 2002); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXLTL-NT (Sheldrick, 2008); program(s) used to refine structure: SHELXLTL-NT (Sheldrick, 2008); molecular graphics: SHELXLTL-NT (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXLTL-NT (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level. H atoms have been omited for clarity and dashed lines indicate the donor···acceptor interactions for the hydrogen bonds.
	Fig. 2. View of the one-dimensional ribbons along the a axis, generated by intermolecular hydrogen bonds. Intramolecular hydrogen bonds are also shown (dashed lines). Most H atoms have been omited for clarity

(Z)-3-Chloro-3-phenyl-N-[(S)-1-phenylethyl]prop-2-enamide top

Crystal data top

C₁₇H₁₆ClNO	F(000) = 1200
M_r = 285.76	D_x = 1.242 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2ac 2ab	Cell parameters from 16200 reflections
a = 9.803 (3) Å	θ = 1.7–27.5°
b = 14.976 (5) Å	µ = 0.25 mm⁻¹
c = 20.823 (6) Å	T = 293 K
V = 3057.2 (15) Å³	Block, colourless
Z = 8	0.48 × 0.38 × 0.28 mm

Data collection top

Rigaku AFC-7S Mercury diffractometer	5802 independent reflections
Radiation source: Normal-focus sealed tube	3687 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ω scans	θ_max = 28.0°, θ_min = 1.7°
Absorption correction: multi-scan (Jacobson, 1998)	h = −8→11
T_min = 0.897, T_max = 0.985	k = −17→17
32660 measured reflections	l = −24→24

Refinement top

Refinement on F²	Hydrogen site location: difmap and geom
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.070	w = 1/[σ²(F_o²) + (0.0533P)² + 1.3975P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.161	(Δ/σ)_max < 0.001
S = 1.07	Δρ_max = 0.18 e Å⁻³
5802 reflections	Δρ_min = −0.28 e Å⁻³
362 parameters	Extinction correction: SHELXLTL-NT (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0040 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1693 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.03 (9)

Crystal data top

C₁₇H₁₆ClNO	V = 3057.2 (15) Å³
M_r = 285.76	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.803 (3) Å	µ = 0.25 mm⁻¹
b = 14.976 (5) Å	T = 293 K
c = 20.823 (6) Å	0.48 × 0.38 × 0.28 mm

Data collection top

Rigaku AFC-7S Mercury diffractometer	5802 independent reflections
Absorption correction: multi-scan (Jacobson, 1998)	3687 reflections with I > 2σ(I)
T_min = 0.897, T_max = 0.985	R_int = 0.063
32660 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	H-atom parameters constrained
wR(F²) = 0.161	Δρ_max = 0.18 e Å⁻³
S = 1.07	Δρ_min = −0.28 e Å⁻³
5802 reflections	Absolute structure: Flack (1983), 1693 Friedel pairs
362 parameters	Absolute structure parameter: −0.03 (9)
0 restraints

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

	x	y	z	U_iso*/U_eq
Cl1	0.22516 (10)	0.07828 (9)	0.67679 (6)	0.0689 (4)
Cl2	0.67708 (13)	−0.13296 (11)	0.71017 (7)	0.0894 (5)
O1	0.1409 (3)	−0.0600 (2)	0.58351 (14)	0.0657 (9)
O2	0.6351 (3)	−0.0446 (3)	0.58420 (16)	0.0829 (11)
N1	−0.0829 (3)	−0.0843 (2)	0.56625 (16)	0.0500 (9)
H1N	−0.1799	−0.0749	0.5718	0.075*
N2	0.4251 (4)	−0.0362 (3)	0.54294 (19)	0.0606 (10)
H2N	0.3285	−0.0424	0.5436	0.091*
C1	0.0512 (4)	0.0668 (3)	0.68930 (19)	0.0472 (10)
C2	−0.0235 (4)	0.0157 (3)	0.6501 (2)	0.0545 (12)
H2	−0.1172	0.0186	0.6567	0.065*
C3	0.0199 (4)	−0.0450 (3)	0.5976 (2)	0.0530 (11)
C4	−0.0595 (4)	−0.1488 (3)	0.5152 (2)	0.0505 (11)
H4	0.0189	−0.1856	0.5275	0.061*
C5	−0.0041 (4)	0.1173 (3)	0.7437 (2)	0.0559 (12)
C6	−0.1234 (5)	0.0899 (3)	0.7744 (2)	0.0677 (13)
H6	−0.1676	0.0382	0.7610	0.081*
C7	−0.1763 (5)	0.1392 (4)	0.8244 (2)	0.0772 (15)
H7	−0.2560	0.1202	0.8445	0.093*
C8	−0.1139 (5)	0.2153 (4)	0.8451 (2)	0.0749 (15)
H8	−0.1520	0.2489	0.8781	0.090*
C9	0.0041 (5)	0.2415 (4)	0.8171 (2)	0.0771 (15)
H9	0.0488	0.2921	0.8322	0.092*
C10	0.0592 (5)	0.1940 (4)	0.7663 (3)	0.0736 (15)
H10	0.1394	0.2137	0.7471	0.088*
C11	−0.1834 (5)	−0.2102 (3)	0.5095 (3)	0.0742 (15)
H11A	−0.2015	−0.2374	0.5503	0.111*
H11B	−0.1652	−0.2558	0.4782	0.111*
H11C	−0.2613	−0.1760	0.4963	0.111*
C12	−0.0270 (4)	−0.1055 (3)	0.4513 (2)	0.0498 (11)
C13	−0.0587 (5)	−0.0188 (3)	0.4370 (2)	0.0660 (13)
H13	−0.1011	0.0165	0.4679	0.079*
C14	−0.0291 (6)	0.0174 (4)	0.3779 (3)	0.0816 (16)
H14	−0.0522	0.0762	0.3688	0.098*
C15	0.0353 (6)	−0.0344 (4)	0.3321 (3)	0.0823 (17)
H15	0.0554	−0.0101	0.2921	0.099*
C16	0.0697 (5)	−0.1213 (4)	0.3450 (2)	0.0748 (15)
H16	0.1129	−0.1561	0.3141	0.090*
C17	0.0391 (4)	−0.1558 (3)	0.4044 (2)	0.0598 (13)
H17	0.0633	−0.2145	0.4135	0.072*
C18	0.5007 (4)	−0.1343 (3)	0.6992 (2)	0.0566 (12)
C19	0.4457 (4)	−0.0998 (3)	0.6462 (2)	0.0562 (12)
H19	0.3510	−0.1024	0.6444	0.067*
C20	0.5118 (4)	−0.0577 (3)	0.5898 (2)	0.0564 (12)
C21	0.4705 (5)	−0.0075 (4)	0.4790 (2)	0.0692 (14)
H21	0.5526	−0.0416	0.4682	0.083*
C22	0.4252 (5)	−0.1776 (3)	0.7526 (2)	0.0643 (13)
C23	0.2911 (5)	−0.1517 (4)	0.7646 (2)	0.0753 (15)
H23	0.2495	−0.1081	0.7395	0.090*
C24	0.2199 (7)	−0.1923 (5)	0.8150 (3)	0.104 (2)
H24	0.1321	−0.1733	0.8250	0.125*
C25	0.2783 (10)	−0.2597 (6)	0.8497 (3)	0.118 (3)
H25	0.2282	−0.2879	0.8817	0.141*
C26	0.4087 (9)	−0.2858 (5)	0.8380 (3)	0.110 (2)
H26	0.4480	−0.3314	0.8620	0.132*
C27	0.4825 (6)	−0.2440 (4)	0.7900 (3)	0.0804 (16)
H27	0.5725	−0.2608	0.7827	0.096*
C28	0.3596 (6)	−0.0315 (4)	0.4295 (2)	0.0913 (18)
H28A	0.3381	−0.0938	0.4328	0.137*
H28B	0.3924	−0.0188	0.3870	0.137*
H28C	0.2792	0.0032	0.4377	0.137*
C29	0.5052 (5)	0.0901 (4)	0.4736 (2)	0.0669 (14)
C30	0.4374 (6)	0.1545 (4)	0.5075 (3)	0.0836 (16)
H30	0.3710	0.1374	0.5370	0.100*
C31	0.4653 (8)	0.2447 (5)	0.4992 (4)	0.107 (2)
H31	0.4184	0.2873	0.5231	0.128*
C32	0.5621 (9)	0.2707 (5)	0.4559 (4)	0.113 (2)
H32	0.5811	0.3310	0.4502	0.136*
C33	0.6305 (7)	0.2085 (6)	0.4209 (4)	0.118 (3)
H33	0.6956	0.2267	0.3912	0.142*
C34	0.6043 (6)	0.1177 (5)	0.4292 (3)	0.0914 (19)
H34	0.6523	0.0757	0.4053	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0419 (6)	0.0814 (9)	0.0833 (9)	−0.0033 (6)	0.0006 (5)	−0.0198 (7)
Cl2	0.0494 (7)	0.1156 (12)	0.1032 (11)	0.0039 (7)	−0.0093 (7)	0.0216 (9)
O1	0.0387 (17)	0.089 (3)	0.069 (2)	0.0026 (16)	0.0028 (14)	−0.0176 (18)
O2	0.0356 (18)	0.127 (3)	0.086 (2)	0.0029 (17)	0.0049 (16)	0.012 (2)
N1	0.0369 (18)	0.063 (2)	0.050 (2)	−0.0017 (17)	−0.0002 (15)	−0.0064 (19)
N2	0.0381 (19)	0.074 (3)	0.070 (3)	−0.0029 (18)	−0.0024 (18)	0.005 (2)
C1	0.035 (2)	0.058 (3)	0.049 (3)	−0.003 (2)	−0.0022 (18)	0.002 (2)
C2	0.042 (2)	0.063 (3)	0.059 (3)	0.002 (2)	0.006 (2)	0.005 (2)
C3	0.051 (3)	0.059 (3)	0.049 (3)	0.002 (2)	0.003 (2)	−0.002 (2)
C4	0.050 (2)	0.053 (3)	0.049 (3)	0.003 (2)	−0.007 (2)	0.003 (2)
C5	0.050 (2)	0.072 (3)	0.046 (3)	0.002 (2)	0.001 (2)	−0.004 (2)
C6	0.067 (3)	0.074 (4)	0.062 (3)	−0.011 (3)	0.017 (2)	−0.013 (3)
C7	0.068 (3)	0.099 (4)	0.065 (3)	−0.007 (3)	0.022 (3)	−0.015 (3)
C8	0.071 (3)	0.092 (4)	0.061 (3)	0.006 (3)	0.010 (3)	−0.023 (3)
C9	0.077 (3)	0.081 (4)	0.073 (4)	−0.010 (3)	0.013 (3)	−0.025 (3)
C10	0.059 (3)	0.085 (4)	0.077 (4)	−0.010 (3)	0.002 (3)	−0.019 (3)
C11	0.080 (3)	0.068 (4)	0.075 (3)	−0.023 (3)	−0.010 (3)	−0.003 (3)
C12	0.048 (2)	0.060 (3)	0.042 (3)	−0.004 (2)	−0.0019 (18)	−0.002 (2)
C13	0.086 (4)	0.056 (3)	0.056 (3)	0.004 (3)	0.003 (3)	0.006 (3)
C14	0.110 (5)	0.059 (4)	0.076 (4)	0.000 (3)	0.005 (3)	0.018 (3)
C15	0.103 (4)	0.086 (5)	0.058 (3)	−0.022 (3)	0.011 (3)	0.007 (3)
C16	0.085 (4)	0.087 (4)	0.053 (3)	−0.004 (3)	0.010 (3)	−0.009 (3)
C17	0.057 (3)	0.067 (3)	0.055 (3)	0.001 (2)	−0.001 (2)	−0.009 (3)
C18	0.042 (2)	0.062 (3)	0.066 (3)	0.004 (2)	0.000 (2)	−0.011 (3)
C19	0.039 (2)	0.068 (3)	0.061 (3)	−0.001 (2)	0.004 (2)	−0.002 (3)
C20	0.037 (2)	0.063 (3)	0.069 (3)	0.004 (2)	0.003 (2)	−0.005 (2)
C21	0.057 (3)	0.083 (4)	0.067 (3)	0.006 (3)	0.007 (2)	0.004 (3)
C22	0.065 (3)	0.067 (3)	0.060 (3)	−0.007 (3)	−0.001 (3)	−0.017 (3)
C23	0.069 (3)	0.083 (4)	0.073 (3)	−0.011 (3)	0.010 (3)	−0.008 (3)
C24	0.089 (4)	0.123 (6)	0.100 (5)	−0.024 (4)	0.035 (4)	−0.025 (5)
C25	0.155 (8)	0.132 (7)	0.066 (4)	−0.041 (6)	0.025 (5)	−0.001 (4)
C26	0.150 (7)	0.110 (6)	0.070 (4)	−0.006 (5)	0.011 (5)	0.012 (4)
C27	0.093 (4)	0.091 (4)	0.058 (3)	0.001 (3)	−0.006 (3)	0.005 (3)
C28	0.101 (4)	0.100 (5)	0.073 (4)	−0.022 (3)	−0.018 (3)	0.002 (3)
C29	0.050 (3)	0.088 (4)	0.062 (3)	−0.002 (3)	−0.005 (2)	0.009 (3)
C30	0.083 (4)	0.084 (5)	0.084 (4)	−0.003 (3)	0.006 (3)	0.007 (3)
C31	0.137 (6)	0.075 (5)	0.108 (5)	−0.003 (4)	0.003 (5)	0.011 (4)
C32	0.127 (6)	0.088 (6)	0.124 (7)	−0.021 (5)	−0.027 (5)	0.024 (5)
C33	0.098 (5)	0.124 (7)	0.133 (7)	−0.027 (5)	−0.004 (5)	0.062 (6)
C34	0.071 (4)	0.108 (5)	0.096 (5)	−0.003 (3)	0.012 (3)	0.019 (4)

Geometric parameters (Å, º) top

Cl1—C1	1.734 (4)	C15—C16	1.370 (7)
Cl2—C18	1.745 (4)	C15—H15	0.9300
O1—C3	1.242 (5)	C16—C17	1.374 (7)
O2—C20	1.231 (5)	C16—H16	0.9300
N1—C3	1.338 (5)	C17—H17	0.9300
N1—C4	1.455 (5)	C18—C19	1.332 (6)
N1—H1N	0.9677	C18—C22	1.484 (7)
N2—C20	1.333 (6)	C19—C20	1.483 (6)
N2—C21	1.469 (6)	C19—H19	0.9300
N2—H2N	0.9518	C21—C29	1.504 (8)
C1—C2	1.338 (6)	C21—C28	1.541 (7)
C1—C5	1.467 (6)	C21—H21	0.9800
C2—C3	1.483 (6)	C22—C27	1.382 (7)
C2—H2	0.9300	C22—C23	1.394 (7)
C4—C12	1.513 (6)	C23—C24	1.399 (8)
C4—C11	1.528 (6)	C23—H23	0.9300
C4—H4	0.9800	C24—C25	1.367 (10)
C5—C10	1.387 (7)	C24—H24	0.9300
C5—C6	1.394 (6)	C25—C26	1.359 (9)
C6—C7	1.378 (6)	C25—H25	0.9300
C6—H6	0.9300	C26—C27	1.385 (8)
C7—C8	1.363 (7)	C26—H26	0.9300
C7—H7	0.9300	C27—H27	0.9300
C8—C9	1.353 (7)	C28—H28A	0.9600
C8—H8	0.9300	C28—H28B	0.9600
C9—C10	1.385 (7)	C28—H28C	0.9600
C9—H9	0.9300	C29—C30	1.368 (7)
C10—H10	0.9300	C29—C34	1.404 (7)
C11—H11A	0.9600	C30—C31	1.390 (8)
C11—H11B	0.9600	C30—H30	0.9300
C11—H11C	0.9600	C31—C32	1.366 (10)
C12—C13	1.369 (6)	C31—H31	0.9300
C12—C17	1.394 (6)	C32—C33	1.359 (10)
C13—C14	1.376 (7)	C32—H32	0.9300
C13—H13	0.9300	C33—C34	1.394 (9)
C14—C15	1.382 (7)	C33—H33	0.9300
C14—H14	0.9300	C34—H34	0.9300

C3—N1—C4	122.0 (3)	C16—C17—C12	121.9 (5)
C3—N1—H1N	128.2	C16—C17—H17	119.0
C4—N1—H1N	109.8	C12—C17—H17	119.0
C20—N2—C21	122.8 (4)	C19—C18—C22	126.0 (4)
C20—N2—H2N	126.9	C19—C18—Cl2	120.3 (4)
C21—N2—H2N	110.1	C22—C18—Cl2	113.7 (4)
C2—C1—C5	124.4 (4)	C18—C19—C20	130.1 (4)
C2—C1—Cl1	120.2 (3)	C18—C19—H19	114.9
C5—C1—Cl1	115.4 (3)	C20—C19—H19	114.9
C1—C2—C3	130.1 (4)	O2—C20—N2	121.2 (4)
C1—C2—H2	115.0	O2—C20—C19	124.9 (4)
C3—C2—H2	115.0	N2—C20—C19	113.9 (4)
O1—C3—N1	121.6 (4)	N2—C21—C29	114.9 (4)
O1—C3—C2	124.0 (4)	N2—C21—C28	108.9 (4)
N1—C3—C2	114.4 (4)	C29—C21—C28	109.6 (4)
N1—C4—C12	113.0 (3)	N2—C21—H21	107.7
N1—C4—C11	109.3 (4)	C29—C21—H21	107.7
C12—C4—C11	110.9 (3)	C28—C21—H21	107.7
N1—C4—H4	107.8	C27—C22—C23	118.9 (5)
C12—C4—H4	107.8	C27—C22—C18	122.2 (5)
C11—C4—H4	107.8	C23—C22—C18	118.9 (5)
C10—C5—C6	117.7 (4)	C22—C23—C24	118.9 (6)
C10—C5—C1	121.5 (4)	C22—C23—H23	120.5
C6—C5—C1	120.8 (4)	C24—C23—H23	120.5
C7—C6—C5	120.3 (5)	C25—C24—C23	120.6 (6)
C7—C6—H6	119.9	C25—C24—H24	119.7
C5—C6—H6	119.9	C23—C24—H24	119.7
C8—C7—C6	121.2 (5)	C26—C25—C24	120.8 (7)
C8—C7—H7	119.4	C26—C25—H25	119.6
C6—C7—H7	119.4	C24—C25—H25	119.6
C9—C8—C7	119.4 (5)	C25—C26—C27	119.4 (7)
C9—C8—H8	120.3	C25—C26—H26	120.3
C7—C8—H8	120.3	C27—C26—H26	120.3
C8—C9—C10	120.9 (5)	C22—C27—C26	121.3 (6)
C8—C9—H9	119.6	C22—C27—H27	119.3
C10—C9—H9	119.6	C26—C27—H27	119.3
C9—C10—C5	120.6 (5)	C21—C28—H28A	109.5
C9—C10—H10	119.7	C21—C28—H28B	109.5
C5—C10—H10	119.7	H28A—C28—H28B	109.5
C4—C11—H11A	109.5	C21—C28—H28C	109.5
C4—C11—H11B	109.5	H28A—C28—H28C	109.5
H11A—C11—H11B	109.5	H28B—C28—H28C	109.5
C4—C11—H11C	109.5	C30—C29—C34	117.9 (6)
H11A—C11—H11C	109.5	C30—C29—C21	122.4 (5)
H11B—C11—H11C	109.5	C34—C29—C21	119.5 (5)
C13—C12—C17	117.8 (4)	C29—C30—C31	121.7 (6)
C13—C12—C4	123.4 (4)	C29—C30—H30	119.1
C17—C12—C4	118.8 (4)	C31—C30—H30	119.1
C12—C13—C14	121.3 (5)	C32—C31—C30	119.7 (7)
C12—C13—H13	119.3	C32—C31—H31	120.2
C14—C13—H13	119.3	C30—C31—H31	120.2
C13—C14—C15	119.6 (5)	C33—C32—C31	120.1 (7)
C13—C14—H14	120.2	C33—C32—H32	119.9
C15—C14—H14	120.2	C31—C32—H32	119.9
C16—C15—C14	120.6 (5)	C32—C33—C34	120.8 (7)
C16—C15—H15	119.7	C32—C33—H33	119.6
C14—C15—H15	119.7	C34—C33—H33	119.6
C15—C16—C17	118.7 (5)	C33—C34—C29	119.8 (7)
C15—C16—H16	120.6	C33—C34—H34	120.1
C17—C16—H16	120.6	C29—C34—H34	120.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.97	1.89	2.852 (4)	174
N2—H2N···O1	0.95	2.04	2.933 (5)	157
C10—H10···Cl1	0.93	2.64	3.021 (6)	105
C13—H13···N1	0.93	2.55	2.874 (5)	101
C19—H19···O1	0.93	2.50	3.315 (5)	146
C27—H27···Cl2	0.93	2.65	3.028 (6)	105
C30—H30···N2	0.93	2.65	2.951 (5)	99

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆ClNO
M_r	285.76
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	9.803 (3), 14.976 (5), 20.823 (6)
V (Å³)	3057.2 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.48 × 0.38 × 0.28

Data collection
Diffractometer	Rigaku AFC-7S Mercury diffractometer
Absorption correction	Multi-scan (Jacobson, 1998)
T_min, T_max	0.897, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	32660, 5802, 3687
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.161, 1.07
No. of reflections	5802
No. of parameters	362
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.28
Absolute structure	Flack (1983), 1693 Friedel pairs
Absolute structure parameter	−0.03 (9)

Computer programs: CrystalClear (Rigaku, 2002), CrystalStructure (Rigaku/MSC, 2004), SHELXLTL-NT (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999), SHELXLTL-NT (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.97	1.89	2.852 (4)	174
N2—H2N···O1	0.95	2.04	2.933 (5)	157
C10—H10···Cl1	0.93	2.64	3.021 (6)	105
C13—H13···N1	0.93	2.55	2.874 (5)	101
C19—H19···O1	0.93	2.50	3.315 (5)	146
C27—H27···Cl2	0.93	2.65	3.028 (6)	105
C30—H30···N2	0.93	2.65	2.951 (5)	99

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors thank FONACIT-MCT Venezuela for financial support (projects: LAB-199700821).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Cherry, K., Abarbri, M., Parían, J.-L. & Duchene, A. (2003). Tetrahedron Lett. 44, 5791–5794. Web of Science CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Jacobson, R. (1998). Private communication to the Rigaku Corporation, Tokyo, Japan. Google Scholar
Kishikawa, K., Satoshi, A., Shigeo, K., Makoto, Y. & Kazutoshi, Y. (1997). J. Chem. Soc. Perkin Trans. 1, pp. 77–84. CrossRef Web of Science Google Scholar
Pontiki, E. & Hadjipavlou, L. (2007). Med. Chem. 3, 175–186. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku (2002). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Urdaneta, N. A., Salazar, J., Herrera, J. & López, S. (2004). Synth. Commun. 34, 657–664. Web of Science CrossRef CAS Google Scholar