3-Chloro­propion­amide

The crystal structure of 3-chloro­propion­amide, C₃H₆ClNO, (I), was determined in order to obtain coordinates for molecular-orbital calculations. Intermolecular N-H...O and C-H...O hydrogen bonds link the mol­ecules into continuous two-dimensional sheets parallel to the (100) plane. The bond distances are C-Cl 1.793 (3), C=O 1.233 (3) and C-N 1.320 (3) Å.

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1990); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.

(I)

Crystal data

C3H6ClNO	Dx = 1.414 Mg m^−3
Mr = 107.54	Mo Kα radiation, λ = 0.7107 Å
Monoclinic, P21/c	Cell parameters from 25 reflections
a = 6.880 (2) Å	θ = 14.2–15.0°
b = 8.201 (3) Å	µ = 0.61 mm^−1
c = 9.298 (2) Å	T = 296 K
β = 105.59 (1)°	Prismatic, colourless
V = 505.3 (2) Å^3	0.20 × 0.15 × 0.15 mm
Z = 4

Data collection

Rigaku AFC-5R diffractometer	Rint = 0.007
ω–2θ scans	θmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = −8→8
Tmin = 0.882, Tmax = 0.913	k = 0→10
1306 measured reflections	l = −12→0
1153 independent reflections	3 standard reflections every 150 reflections
757 reflections with F^2 > 2σ(F^2)	intensity decay: 3.9%

Refinement

Refinement on F^2	w = 1/{σ^2(Fo^2) + [0.08600(Max(Fo^2,0) + 2Fc^2)/3]^2}
R[F^2 > 2σ(F^2)] = 0.035	(Δ/σ)max = 0.007
wR(F^2) = 0.109	Δρmax = 0.22 e Å^−3
S = 0.96	Δρmin = −0.20 e Å^−3
849 reflections	Extinction correction: Zachariasen(1967) type 2 Gaussian isotropic
80 parameters	Extinction coefficient: 0.01 (1)
All H-atom parameters refined

Special details

Refinement. Refinement using reflections with F² > 1.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl(1)	0.13036 (9)	0.23613 (9)	0.61173 (8)	0.0644 (2)
O(1)	−0.3580 (2)	0.1309 (2)	0.6592 (2)	0.0406 (4)
N(1)	−0.4319 (3)	0.1839 (3)	0.4135 (2)	0.0468 (5)
C(1)	−0.3467 (3)	0.2198 (2)	0.5548 (2)	0.0345 (5)
C(2)	−0.2344 (4)	0.3796 (3)	0.5838 (3)	0.0476 (6)
C(3)	−0.0272 (4)	0.3611 (3)	0.6918 (3)	0.0525 (7)
H(1)	−0.409 (4)	0.249 (3)	0.348 (3)	0.050 (7)*
H(2)	−0.504 (4)	0.098 (4)	0.388 (3)	0.058 (7)*
H(3)	0.037 (4)	0.462 (4)	0.717 (3)	0.075 (8)*
H(4)	−0.038 (4)	0.302 (3)	0.786 (3)	0.052 (7)*
H(5)	−0.230 (4)	0.431 (4)	0.493 (3)	0.058 (7)*
H(6)	−0.310 (4)	0.456 (4)	0.632 (3)	0.061 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl(1)	0.0507 (4)	0.0737 (5)	0.0666 (5)	−0.0013 (3)	0.0121 (3)	0.0024 (3)
O(1)	0.0503 (8)	0.0399 (8)	0.0304 (7)	−0.0066 (6)	0.0085 (6)	0.0015 (6)
N(1)	0.056 (1)	0.052 (1)	0.0292 (10)	−0.0139 (9)	0.0058 (8)	0.0030 (9)
C(1)	0.0331 (9)	0.0360 (9)	0.034 (1)	0.0011 (8)	0.0075 (8)	0.0009 (8)
C(2)	0.057 (1)	0.033 (1)	0.050 (1)	−0.0049 (10)	0.008 (1)	0.0007 (9)
C(3)	0.055 (1)	0.053 (1)	0.046 (1)	−0.020 (1)	0.007 (1)	−0.008 (1)

Geometric parameters (Å, º)

Cl(1)—C(3)	1.793 (3)	C(2)—C(3)	1.515 (3)
O(1)—C(1)	1.233 (3)	C(2)—H(5)	0.95 (3)
N(1)—C(1)	1.320 (3)	C(2)—H(6)	0.99 (3)
N(1)—H(1)	0.85 (3)	C(3)—H(3)	0.94 (3)
N(1)—H(2)	0.86 (3)	C(3)—H(4)	1.03 (3)
C(1)—C(2)	1.508 (3)
Cl(1)···H(4)^i	2.95 (3)	C(1)···H(3)^iii	3.33 (3)
Cl(1)···H(5)^ii	3.04 (3)	C(2)···H(1)^vii	3.19 (3)
Cl(1)···H(3)^iii	3.14 (3)	C(2)···H(6)^viii	3.50 (3)
Cl(1)···H(6)^iii	3.30 (3)	C(3)···H(5)^ii	3.26 (3)
Cl(1)···H(1)^iv	3.34 (3)	C(3)···H(3)^iii	3.38 (3)
Cl(1)···H(2)^iv	3.36 (3)	C(3)···H(1)^vii	3.45 (3)
Cl(1)···O(1)^v	3.535 (2)	C(3)···H(2)^iv	3.59 (3)
Cl(1)···N(1)^iv	3.582 (2)	H(1)···H(4)^i	2.80 (4)
O(1)···H(3)^iii	2.60 (3)	H(1)···H(6)^i	2.84 (4)
O(1)···N(1)^vi	2.947 (3)	H(1)···H(6)^viii	3.13 (4)
O(1)···N(1)^vii	2.966 (3)	H(1)···H(2)^ix	3.56 (4)
O(1)···H(5)^vii	3.04 (3)	H(2)···H(2)^vi	2.61 (6)
O(1)···H(2)^vii	3.41 (3)	H(2)···H(6)^i	3.07 (4)
O(1)···C(3)^iii	3.444 (3)	H(2)···H(3)^x	3.17 (4)
O(1)···H(1)^vi	3.50 (3)	H(3)···H(4)^xi	2.78 (4)
N(1)···H(2)^vi	3.06 (3)	H(3)···H(5)^ii	2.79 (4)
N(1)···H(6)^i	3.17 (3)	H(4)···H(5)^vii	3.24 (4)
N(1)···H(4)^i	3.24 (3)	H(5)···H(6)^viii	3.20 (4)
N(1)···H(6)^viii	3.41 (3)	H(5)···H(5)^ii	3.33 (5)
C(1)···H(1)^vii	2.89 (3)	H(6)···H(6)^viii	3.15 (5)
C(1)···H(2)^vi	2.90 (3)
C(1)—N(1)—H(1)	116 (1)	C(3)—C(2)—H(5)	112 (1)
C(1)—N(1)—H(2)	121 (1)	C(3)—C(2)—H(6)	106 (1)
H(1)—N(1)—H(2)	121 (2)	H(5)—C(2)—H(6)	105 (2)
O(1)—C(1)—N(1)	123.2 (2)	Cl(1)—C(3)—C(2)	110.4 (2)
O(1)—C(1)—C(2)	120.7 (2)	Cl(1)—C(3)—H(3)	108 (1)
N(1)—C(1)—C(2)	116.1 (2)	Cl(1)—C(3)—H(4)	105 (1)
C(1)—C(2)—C(3)	112.2 (2)	C(2)—C(3)—H(3)	111 (1)
C(1)—C(2)—H(5)	111 (1)	C(2)—C(3)—H(4)	110 (1)
C(1)—C(2)—H(6)	108 (1)	H(3)—C(3)—H(4)	109 (2)
Cl(1)—C(3)—C(2)—C(1)	65.2 (3)	N(1)—C(1)—C(2)—C(3)	−132.2 (2)
O(1)—C(1)—C(2)—C(3)	48.6 (3)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, −y+1, −z+1; (iii) −x, y−1/2, −z+3/2; (iv) x+1, −y+1/2, z+1/2; (v) x+1, y, z; (vi) −x−1, −y, −z+1; (vii) x, −y+1/2, z+1/2; (viii) −x−1, −y+1, −z+1; (ix) −x−1, y+1/2, −z+1/2; (x) x−1, −y+1/2, z−1/2; (xi) −x, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.86 (3)	2.12 (3)	2.967 (3)	169 (2)
N1—H2···O1^vi	0.86 (3)	2.10 (3)	2.947 (3)	172 (3)
C3—H3···O1^xi	0.94 (3)	2.60 (3)	3.445 (3)	150 (2)

Symmetry codes: (i) x, −y+1/2, z−1/2; (vi) −x−1, −y, −z+1; (xi) −x, y+1/2, −z+3/2.