N-(5-Chloro-2-nitro-phen-yl)-2,2-di-methyl-propanamide.

In the crystal structure of the title compound, C(11)H(13)ClN(2)O(3), mol-ecules are linked through C-H⋯O hydrogen bonds.

Related literature

For background to the biologically active mol­ecule ezetimibe [systematic name: (3R,4S)-1-(4-fluoro­phen­yl)-3-[(3S)-3-(4-fluoro­phen­yl)-3-hy­droxy­prop­yl]-4-(4-hy­droxy­phen­yl)azetidin-2-one, see: Rosenblum et al. (1998 ▶). For the preparation of the title compound, a derivative of an inter­mediate in the synthesis of ezetimibe, see: Wang et al. (2009) ▶. For a related structure, see: Zhu et al. (2007 ▶).

Experimental

Crystal data

C11H12ClN2O3

M = 255.68

Orthorhombic,

a = 10.401 (2) Å

b = 7.0280 (14) Å

c = 17.106 (3) Å

V = 1250.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.915, T max = 0.970

2432 measured reflections

1244 independent reflections

643 reflections with I > 2σ(I)

R int = 0.069

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.179

S = 1.00

1244 reflections

94 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812027730/zj2083sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027730/zj2083Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027730/zj2083Isup3.cml

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

C11H12ClN2O3	F(000) = 532
Mr = 255.68	Dx = 1.358 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 25 reflections
a = 10.401 (2) Å	θ = 9–12°
b = 7.0280 (14) Å	µ = 0.30 mm−1
c = 17.106 (3) Å	T = 293 K
V = 1250.4 (4) Å3	Block, colorless
Z = 4	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	643 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.069
Graphite monochromator	θmax = 25.4°, θmin = 2.3°
ω/2θ scans	h = 0→12
Absorption correction: ψ scan (North et al., 1968)	k = −8→0
Tmin = 0.915, Tmax = 0.970	l = −20→20
2432 measured reflections	3 standard reflections every 200 reflections
1244 independent reflections	intensity decay: 1%

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.084P)2] where P = (Fo2 + 2Fc2)/3
1244 reflections	(Δ/σ)max < 0.001
94 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.22 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)
Cl	0.24447 (9)	0.2500	0.50682 (10)	0.0967 (6)
N1	0.7748 (5)	0.2500	0.3855 (3)	0.0880 (14)
C1	0.4982 (4)	0.2500	0.5237 (3)	0.0623 (11)
H1A	0.4794	0.2500	0.5769	0.075*
O1	0.7853 (5)	0.2500	0.3151 (3)	0.143 (2)
N2	0.7290 (3)	0.2500	0.5525 (2)	0.0706 (11)
H2A	0.8046	0.2500	0.5321	0.085*
O2	0.8711 (4)	0.2500	0.4258 (3)	0.1202 (15)
C2	0.4005 (4)	0.2500	0.4726 (3)	0.0664 (12)
O3	0.6267 (3)	0.2500	0.6688 (2)	0.1179 (16)
C3	0.4218 (5)	0.2500	0.3921 (3)	0.0824 (15)
H3A	0.3541	0.2500	0.3565	0.099*
C4	0.5469 (7)	0.2500	0.3681 (3)	0.0964 (18)
H4A	0.5640	0.2500	0.3147	0.116*
C5	0.6479 (4)	0.2500	0.4186 (3)	0.0732 (13)
C6	0.6275 (4)	0.2500	0.5004 (3)	0.0585 (11)
C7	0.7243 (4)	0.2500	0.6321 (3)	0.0720 (14)
C8	0.8531 (4)	0.2500	0.6754 (3)	0.0802 (15)
C9	0.9244 (4)	0.4286 (7)	0.6607 (3)	0.156
H9A	0.9438	0.4385	0.6060	0.233*
H9B	1.0029	0.4280	0.6902	0.233*
H9C	0.8726	0.5351	0.6763	0.233*
C10	0.8297 (7)	0.2500	0.7644 (4)	0.148 (3)
H10A	0.9098	0.2500	0.7922	0.222*
H10B	0.7814	0.3615	0.7780	0.222*	0.50

	U11	U22	U33	U12	U13	U23
Cl	0.0576 (8)	0.0846 (10)	0.1478 (14)	0.000	−0.0208 (7)	0.000
N1	0.091 (3)	0.067 (3)	0.106 (4)	0.000	0.027 (3)	0.000
C1	0.066 (3)	0.043 (2)	0.078 (3)	0.000	−0.013 (3)	0.000
O1	0.168 (4)	0.172 (5)	0.089 (3)	0.000	0.042 (3)	0.000
N2	0.062 (2)	0.075 (3)	0.074 (3)	0.000	−0.001 (2)	0.000
O2	0.087 (3)	0.146 (4)	0.128 (4)	0.000	0.040 (3)	0.000
C2	0.053 (2)	0.045 (2)	0.101 (3)	0.000	−0.015 (2)	0.000
O3	0.060 (2)	0.215 (5)	0.078 (2)	0.000	−0.0037 (18)	0.000
C3	0.088 (4)	0.058 (3)	0.101 (4)	0.000	−0.038 (3)	0.000
C4	0.138 (5)	0.072 (4)	0.079 (4)	0.000	−0.017 (4)	0.000
C5	0.068 (3)	0.059 (3)	0.093 (4)	0.000	0.015 (3)	0.000
C6	0.061 (2)	0.041 (2)	0.074 (3)	0.000	0.000 (2)	0.000
C7	0.048 (2)	0.076 (4)	0.092 (4)	0.000	−0.011 (3)	0.000
C8	0.058 (3)	0.071 (3)	0.111 (4)	0.000	−0.012 (3)	0.000
C9	0.156	0.156	0.156	0.000	0.000	0.000
C10	0.132 (6)	0.175 (8)	0.136 (6)	0.000	−0.015 (5)	0.000

Cl—C2	1.725 (4)	C3—H3A	0.9300
N1—O1	1.211 (6)	C4—C5	1.360 (7)
N1—O2	1.215 (6)	C4—H4A	0.9300
N1—C5	1.436 (6)	C5—C6	1.415 (6)
C1—C2	1.340 (6)	C7—C8	1.530 (6)
C1—C6	1.403 (6)	C8—C9	1.479 (5)
C1—H1A	0.9300	C8—C9i	1.479 (5)
N2—C7	1.363 (6)	C8—C10	1.540 (8)
N2—C6	1.381 (5)	C9—H9A	0.9600
N2—H2A	0.8600	C9—H9B	0.9600
C2—C3	1.396 (7)	C9—H9C	0.9600
O3—C7	1.194 (5)	C10—H10A	0.9600
C3—C4	1.365 (7)	C10—H10B	0.9600
O1—N1—O2	119.3 (5)	N2—C6—C1	123.3 (4)
O1—N1—C5	118.4 (6)	N2—C6—C5	121.6 (4)
O2—N1—C5	122.3 (5)	C1—C6—C5	115.1 (4)
C2—C1—C6	122.7 (4)	O3—C7—N2	123.8 (4)
C2—C1—H1A	118.6	O3—C7—C8	119.3 (5)
C6—C1—H1A	118.6	N2—C7—C8	116.9 (4)
C7—N2—C6	128.1 (4)	C9—C8—C9i	116.1 (5)
C7—N2—H2A	115.9	C9—C8—C7	110.8 (3)
C6—N2—H2A	115.9	C9i—C8—C7	110.8 (3)
C1—C2—C3	121.6 (4)	C9—C8—C10	104.3 (4)
C1—C2—Cl	119.5 (4)	C9i—C8—C10	104.3 (4)
C3—C2—Cl	118.9 (4)	C7—C8—C10	109.9 (5)
C4—C3—C2	116.6 (5)	C8—C9—H9A	109.5
C4—C3—H3A	121.7	C8—C9—H9B	109.5
C2—C3—H3A	121.7	H9A—C9—H9B	109.5
C5—C4—C3	123.0 (5)	C8—C9—H9C	109.5
C5—C4—H4A	118.5	H9A—C9—H9C	109.5
C3—C4—H4A	118.5	H9B—C9—H9C	109.5
C4—C5—C6	120.9 (4)	C8—C10—H10A	110.7
C4—C5—N1	117.3 (5)	C8—C10—H10B	108.8
C6—C5—N1	121.8 (5)	H10A—C10—H10B	109.5
C6—C1—C2—C3	0.000 (1)	C2—C1—C6—C5	0.000 (1)
C6—C1—C2—Cl	180.0	C4—C5—C6—N2	180.0
C1—C2—C3—C4	0.000 (1)	N1—C5—C6—N2	0.000 (1)
Cl—C2—C3—C4	180.0	C4—C5—C6—C1	0.0
C2—C3—C4—C5	0.000 (1)	N1—C5—C6—C1	180.0
C3—C4—C5—C6	0.000 (1)	C6—N2—C7—O3	0.000 (2)
C3—C4—C5—N1	180.000 (1)	C6—N2—C7—C8	180.000 (1)
O1—N1—C5—C4	0.000 (1)	O3—C7—C8—C9	−114.8 (4)
O2—N1—C5—C4	180.000 (1)	N2—C7—C8—C9	65.2 (4)
O1—N1—C5—C6	180.0	O3—C7—C8—C9i	114.8 (4)
O2—N1—C5—C6	0.000 (1)	N2—C7—C8—C9i	−65.2 (4)
C7—N2—C6—C1	0.000 (1)	O3—C7—C8—C10	0.000 (2)
C7—N2—C6—C5	180.000 (1)	N2—C7—C8—C10	180.000 (2)
C2—C1—C6—N2	180.0

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O3ii	0.96	2.35	3.294 (8)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O3i	0.96	2.35	3.294 (8)	167

Symmetry code: (i) .