(Z)-Isobutyl 2-benzamido-3-(4-chloro-phen-yl)acrylate.

The title compound, C(20)H(20)ClNO(3), 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 mol-ecular conformation is stabilized by an intra-molecular C-H⋯N hydrogen bond. In the crystal structure, centrosymmetrically related mol-ecules inter-act through inter-molecular C-H⋯O hydrogen-bond inter-actions, 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 ▶); Peggion et al. (2003 ▶).

Experimental

Crystal data

C20H20ClNO3

M = 357.82

Triclinic,

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 ▶) T min = 0.897, T max = 0.946

9082 measured reflections

3380 independent reflections

2224 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 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

Data collection: CrystalClear (Rigaku/MSC, 2000 ▶); cell refinement: CrystalClear; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809043931/rz2372sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043931/rz2372Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H20ClNO3	Z = 2
Mr = 357.82	F(000) = 376
Triclinic, P1	Dx = 1.271 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 5.0179 (10) Å	Cell parameters from 2536 reflections
b = 12.581 (2) Å	θ = 3.3–25.3°
c = 16.293 (3) Å	µ = 0.22 mm−1
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

Rigaku AFC-7S Mercury diffractometer	3380 independent reflections
Radiation source: fine-focus sealed tube	2224 reflections with I > 2σ(I)
graphite	Rint = 0.036
Detector resolution: 7.31 pixels mm-1	θmax = 25.4°, θmin = 3.3°
ω scans	h = −6→5
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −15→15
Tmin = 0.897, Tmax = 0.946	l = −19→19
9082 measured reflections

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.213	H 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 parameters	Δρmax = 0.40 e Å−3
5 restraints	Δρmin = −0.37 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	1.2590 (3)	0.91744 (12)	0.10142 (11)	0.1191 (6)
O1	0.3603 (6)	0.3847 (3)	0.09779 (16)	0.0827 (9)
O2	0.4837 (5)	0.2561 (2)	0.23066 (16)	0.0671 (7)
O3	0.2050 (4)	0.4200 (2)	0.31239 (15)	0.0632 (7)
N1	0.6503 (5)	0.4156 (2)	0.27693 (15)	0.0447 (7)
H1	0.8097	0.4099	0.2946	0.054*
C1	0.4725 (7)	0.3599 (3)	0.1656 (2)	0.0535 (9)
C2	0.6145 (6)	0.4408 (3)	0.18535 (19)	0.0469 (8)
C3	0.7106 (7)	0.5258 (3)	0.1182 (2)	0.0512 (8)
H3	0.6848	0.5267	0.0622	0.061*
C4	0.8503 (7)	0.6182 (3)	0.1178 (2)	0.0502 (8)
C5	1.0086 (9)	0.6722 (4)	0.0447 (2)	0.0761 (12)
H5	1.0296	0.6466	−0.0025	0.091*
C6	1.1369 (10)	0.7627 (4)	0.0391 (3)	0.0880 (14)
H6	1.2450	0.7968	−0.0107	0.106*
C7	1.1039 (8)	0.8020 (3)	0.1076 (3)	0.0712 (11)
C8	0.9483 (10)	0.7509 (4)	0.1812 (3)	0.0811 (13)
H8	0.9275	0.7775	0.2279	0.097*
C9	0.8221 (9)	0.6602 (3)	0.1863 (2)	0.0709 (11)
H9	0.7157	0.6261	0.2366	0.085*
C10	0.4399 (6)	0.4007 (3)	0.33605 (19)	0.0448 (8)
C11	0.5016 (6)	0.3597 (3)	0.43160 (19)	0.0476 (8)
C12	0.7329 (8)	0.2865 (3)	0.4664 (2)	0.0645 (10)
H12	0.8642	0.2623	0.4298	0.077*
C13	0.7701 (10)	0.2483 (4)	0.5579 (3)	0.0851 (14)
H13	0.9260	0.1981	0.5825	0.102*
C14	0.5761 (11)	0.2853 (5)	0.6111 (3)	0.0839 (14)
H14	0.6008	0.2595	0.6718	0.101*
C15	0.3528 (11)	0.3577 (5)	0.5768 (3)	0.0859 (13)
H15	0.2245	0.3834	0.6133	0.103*
C16	0.3112 (8)	0.3944 (4)	0.4881 (2)	0.0680 (11)
H16	0.1523	0.4436	0.4652	0.082*
C17	0.3195 (10)	0.1773 (4)	0.2212 (3)	0.0856 (14)
H17A	0.3550	0.1721	0.1631	0.103*
H17B	0.1285	0.2063	0.2268	0.103*
C18	0.3886 (8)	0.0619 (4)	0.2908 (3)	0.0781 (12)
H18	0.275 (6)	0.012 (3)	0.281 (2)	0.073 (11)*
C19	0.669 (2)	0.0005 (11)	0.3151 (8)	0.107 (2)*	0.50
H19A	0.7628	0.0472	0.3336	0.160*	0.50
H19B	0.7638	−0.0122	0.2646	0.160*	0.50
H19C	0.6603	−0.0729	0.3629	0.160*	0.50
C19'	0.662 (2)	0.0186 (11)	0.2528 (8)	0.107 (2)*	0.50
H19D	0.7984	0.0599	0.2579	0.160*	0.50
H19E	0.6450	0.0320	0.1913	0.160*	0.50
H19F	0.7126	−0.0632	0.2853	0.160*	0.50
C20	0.262 (2)	0.0812 (11)	0.3758 (7)	0.101 (2)*	0.50
H20A	0.2481	0.0073	0.4224	0.152*	0.50
H20B	0.0847	0.1264	0.3638	0.152*	0.50
H20C	0.3748	0.1218	0.3937	0.152*	0.50
C20'	0.422 (2)	0.0469 (11)	0.3842 (7)	0.101 (2)*	0.50
H20D	0.4701	−0.0342	0.4191	0.152*	0.50
H20E	0.2546	0.0770	0.4076	0.152*	0.50
H20F	0.5625	0.0883	0.3862	0.152*	0.50

	U11	U22	U33	U12	U13	U23
Cl1	0.1242 (12)	0.0830 (9)	0.1589 (14)	−0.0548 (8)	−0.0204 (10)	−0.0333 (9)
O1	0.116 (2)	0.088 (2)	0.0517 (14)	−0.0472 (18)	−0.0216 (15)	−0.0154 (14)
O2	0.0817 (18)	0.0547 (16)	0.0676 (15)	−0.0262 (13)	−0.0179 (13)	−0.0148 (13)
O3	0.0374 (13)	0.0924 (19)	0.0553 (13)	−0.0180 (12)	−0.0059 (10)	−0.0178 (13)
N1	0.0384 (13)	0.0568 (17)	0.0390 (13)	−0.0168 (12)	−0.0038 (11)	−0.0129 (12)
C1	0.057 (2)	0.059 (2)	0.0469 (18)	−0.0184 (17)	−0.0037 (16)	−0.0170 (17)
C2	0.0462 (18)	0.056 (2)	0.0393 (16)	−0.0155 (15)	−0.0004 (13)	−0.0148 (15)
C3	0.057 (2)	0.059 (2)	0.0412 (16)	−0.0174 (17)	−0.0015 (14)	−0.0190 (16)
C4	0.0516 (19)	0.052 (2)	0.0432 (16)	−0.0101 (16)	−0.0044 (14)	−0.0117 (15)
C5	0.095 (3)	0.078 (3)	0.059 (2)	−0.039 (2)	0.018 (2)	−0.024 (2)
C6	0.096 (3)	0.086 (3)	0.084 (3)	−0.051 (3)	0.024 (2)	−0.025 (3)
C7	0.066 (2)	0.056 (2)	0.090 (3)	−0.018 (2)	−0.016 (2)	−0.017 (2)
C8	0.117 (4)	0.062 (3)	0.072 (3)	−0.030 (3)	−0.012 (3)	−0.024 (2)
C9	0.098 (3)	0.063 (2)	0.056 (2)	−0.034 (2)	0.005 (2)	−0.0187 (18)
C10	0.0439 (18)	0.0495 (19)	0.0404 (16)	−0.0147 (15)	−0.0017 (14)	−0.0124 (14)
C11	0.0487 (19)	0.051 (2)	0.0432 (16)	−0.0219 (16)	−0.0031 (15)	−0.0103 (15)
C12	0.061 (2)	0.069 (3)	0.0494 (18)	−0.0140 (19)	−0.0051 (17)	−0.0045 (18)
C13	0.082 (3)	0.087 (3)	0.066 (2)	−0.024 (3)	−0.027 (2)	0.004 (2)
C14	0.105 (4)	0.103 (4)	0.047 (2)	−0.054 (3)	−0.002 (2)	−0.016 (2)
C15	0.105 (4)	0.103 (4)	0.055 (2)	−0.029 (3)	0.004 (2)	−0.031 (2)
C16	0.069 (2)	0.085 (3)	0.053 (2)	−0.015 (2)	0.0020 (18)	−0.028 (2)
C17	0.104 (3)	0.068 (3)	0.092 (3)	−0.044 (3)	−0.022 (3)	−0.019 (2)
C18	0.067 (3)	0.060 (3)	0.112 (3)	−0.020 (2)	−0.014 (2)	−0.029 (2)

Cl1—C7	1.734 (4)	C13—C14	1.371 (7)
O1—C1	1.200 (4)	C13—H13	0.9300
O2—C1	1.328 (4)	C14—C15	1.331 (7)
O2—C17	1.458 (4)	C14—H14	0.9300
O3—C10	1.232 (4)	C15—C16	1.365 (5)
N1—C10	1.341 (4)	C15—H15	0.9300
N1—C2	1.426 (4)	C16—H16	0.9300
N1—H1	0.8600	C17—C18	1.470 (6)
C1—C2	1.485 (5)	C17—H17A	0.9700
C2—C3	1.327 (4)	C17—H17B	0.9700
C3—C4	1.459 (5)	C18—C20'	1.483 (10)
C3—H3	0.9300	C18—C19	1.490 (10)
C4—C5	1.375 (5)	C18—C19'	1.540 (11)
C4—C9	1.390 (5)	C18—C20	1.546 (10)
C5—C6	1.377 (6)	C18—H18	0.99 (3)
C5—H5	0.9300	C19—H19A	0.9600
C6—C7	1.367 (6)	C19—H19B	0.9600
C6—H6	0.9300	C19—H19C	0.9600
C7—C8	1.363 (6)	C19'—H19D	0.9600
C8—C9	1.375 (5)	C19'—H19E	0.9600
C8—H8	0.9300	C19'—H19F	0.9600
C9—H9	0.9300	C20—H20A	0.9600
C10—C11	1.489 (4)	C20—H20B	0.9600
C11—C12	1.367 (5)	C20—H20C	0.9600
C11—C16	1.386 (5)	C20'—H20D	0.9600
C12—C13	1.404 (5)	C20'—H20E	0.9600
C12—H12	0.9300	C20'—H20F	0.9600
C1—O2—C17	116.2 (3)	C13—C14—H14	119.7
C10—N1—C2	121.2 (2)	C14—C15—C16	120.3 (4)
C10—N1—H1	119.4	C14—C15—H15	119.8
C2—N1—H1	119.4	C16—C15—H15	119.8
O1—C1—O2	123.0 (3)	C15—C16—C11	121.1 (4)
O1—C1—C2	123.9 (3)	C15—C16—H16	119.4
O2—C1—C2	113.1 (3)	C11—C16—H16	119.4
C3—C2—N1	124.9 (3)	O2—C17—C18	108.7 (3)
C3—C2—C1	118.8 (3)	O2—C17—H17A	110.0
N1—C2—C1	116.2 (3)	C18—C17—H17A	110.0
C2—C3—C4	130.6 (3)	O2—C17—H17B	110.0
C2—C3—H3	114.7	C18—C17—H17B	110.0
C4—C3—H3	114.7	H17A—C17—H17B	108.3
C5—C4—C9	116.9 (3)	C17—C18—C20'	122.0 (6)
C5—C4—C3	119.6 (3)	C17—C18—C19	125.4 (6)
C9—C4—C3	123.4 (3)	C20'—C18—C19	72.4 (7)
C4—C5—C6	122.2 (4)	C17—C18—C19'	100.6 (6)
C4—C5—H5	118.9	C20'—C18—C19'	108.9 (7)
C6—C5—H5	118.9	C17—C18—C20	102.6 (6)
C7—C6—C5	119.3 (4)	C19—C18—C20	104.4 (7)
C7—C6—H6	120.3	C19'—C18—C20	140.7 (7)
C5—C6—H6	120.3	C17—C18—H18	105 (2)
C8—C7—C6	120.3 (4)	C20'—C18—H18	117 (2)
C8—C7—Cl1	119.5 (3)	C19—C18—H18	112 (2)
C6—C7—Cl1	120.2 (3)	C19'—C18—H18	99 (2)
C7—C8—C9	119.9 (4)	C20—C18—H18	105 (2)
C7—C8—H8	120.0	C18—C19—H19A	109.5
C9—C8—H8	120.0	C18—C19—H19B	109.5
C8—C9—C4	121.4 (4)	C18—C19—H19C	109.5
C8—C9—H9	119.3	C18—C19'—H19D	109.5
C4—C9—H9	119.3	C18—C19'—H19E	109.5
O3—C10—N1	121.4 (3)	H19D—C19'—H19E	109.5
O3—C10—C11	121.2 (3)	C18—C19'—H19F	109.5
N1—C10—C11	117.3 (3)	H19D—C19'—H19F	109.5
C12—C11—C16	118.7 (3)	H19E—C19'—H19F	109.5
C12—C11—C10	123.0 (3)	C18—C20—H20A	109.5
C16—C11—C10	118.3 (3)	C18—C20—H20B	109.5
C11—C12—C13	119.3 (4)	C18—C20—H20C	109.5
C11—C12—H12	120.4	C18—C20'—H20D	109.5
C13—C12—H12	120.4	C18—C20'—H20E	109.5
C14—C13—C12	119.9 (4)	H20D—C20'—H20E	109.5
C14—C13—H13	120.1	C18—C20'—H20F	109.5
C12—C13—H13	120.1	H20D—C20'—H20F	109.5
C15—C14—C13	120.6 (4)	H20E—C20'—H20F	109.5
C15—C14—H14	119.7
C17—O2—C1—O1	−8.2 (5)	C3—C4—C9—C8	−177.0 (4)
C17—O2—C1—C2	172.3 (3)	C2—N1—C10—O3	−7.7 (5)
C10—N1—C2—C3	130.9 (4)	C2—N1—C10—C11	172.3 (3)
C10—N1—C2—C1	−52.9 (4)	O3—C10—C11—C12	147.3 (4)
O1—C1—C2—C3	−25.4 (5)	N1—C10—C11—C12	−32.7 (5)
O2—C1—C2—C3	154.1 (3)	O3—C10—C11—C16	−30.4 (5)
O1—C1—C2—N1	158.2 (3)	N1—C10—C11—C16	149.6 (3)
O2—C1—C2—N1	−22.3 (4)	C16—C11—C12—C13	0.3 (5)
N1—C2—C3—C4	−5.6 (6)	C10—C11—C12—C13	−177.4 (3)
C1—C2—C3—C4	178.3 (3)	C11—C12—C13—C14	−0.5 (6)
C2—C3—C4—C5	158.4 (4)	C12—C13—C14—C15	−0.4 (7)
C2—C3—C4—C9	−25.0 (6)	C13—C14—C15—C16	1.3 (7)
C9—C4—C5—C6	0.7 (6)	C14—C15—C16—C11	−1.5 (7)
C3—C4—C5—C6	177.5 (4)	C12—C11—C16—C15	0.6 (6)
C4—C5—C6—C7	−1.0 (7)	C10—C11—C16—C15	178.5 (3)
C5—C6—C7—C8	0.8 (7)	C1—O2—C17—C18	171.3 (3)
C5—C6—C7—Cl1	−178.9 (4)	O2—C17—C18—C20'	43.9 (8)
C6—C7—C8—C9	−0.5 (7)	O2—C17—C18—C19	−46.5 (8)
Cl1—C7—C8—C9	179.3 (3)	O2—C17—C18—C19'	−76.4 (6)
C7—C8—C9—C4	0.3 (7)	O2—C17—C18—C20	71.7 (6)
C5—C4—C9—C8	−0.4 (6)

D—H···A	D—H	H···A	D···A	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

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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) ; (ii) .