Buy article online - an online subscription or single-article purchase is required to access this article.
The crystal structure of 3-chloropropionamide, C
3H
6ClNO, (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.
Supporting information
CCDC reference: 150747
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.
Crystal data top
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) Å3 | 0.20 × 0.15 × 0.15 mm |
Z = 4 | |
Data collection top
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 F2 > 2σ(F2) | intensity decay: 3.9% |
Refinement top
Refinement on F2 | w = 1/{σ2(Fo2) + [0.08600(Max(Fo2,0) + 2Fc2)/3]2} |
R[F2 > 2σ(F2)] = 0.035 | (Δ/σ)max = 0.007 |
wR(F2) = 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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 (3) | 2.12 (3) | 2.967 (3) | 169 (2) |
N1—H2···O1vi | 0.86 (3) | 2.10 (3) | 2.947 (3) | 172 (3) |
C3—H3···O1xi | 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. |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.