Buy article online - an online subscription or single-article purchase is required to access this article.
The title compound, C3H6ClNO, contains two crystallographically independent molecules in the asymmetric unit. A planar molecule (type A) and a slightly twisted molecule (type B) form alternating pairs of adjacent layers parallel to (010). Consecutive type A layers are related through centers of inversion at y = 0 and ½, while type B layers are related by twofold screw axes at y = ¼ and ¾.
Supporting information
CCDC reference: 642905
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.091
- Data-to-parameter ratio = 19.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.04
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.08
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1E .. CL1B .. 2.85 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and SCHAKAL99 (Keller, 1999); software used to prepare material for publication: SHELXL97.
2-Chloro-
N-methylacetamide
top
Crystal data top
C3H6ClNO | F(000) = 448 |
Mr = 107.54 | Dx = 1.475 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2696 reflections |
a = 5.0911 (3) Å | θ = 2.9–28.2° |
b = 26.5090 (17) Å | µ = 0.64 mm−1 |
c = 7.4671 (5) Å | T = 173 K |
β = 106.103 (2)° | Needle, colourless |
V = 968.22 (11) Å3 | 0.32 × 0.08 × 0.07 mm |
Z = 8 | |
Data collection top
Bruker APEX2 CCD area-detector diffractometer | 1757 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.061 |
Graphite monochromator | θmax = 28.0°, θmin = 1.5° |
φ and ω scans | h = −6→6 |
10450 measured reflections | k = −33→35 |
2338 independent reflections | l = −9→9 |
Refinement top
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0471P)2] where P = (Fo2 + 2Fc2)/3 |
2338 reflections | (Δ/σ)max < 0.001 |
119 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Special details top
Experimental. 1H(CDCl3): 2.89 (d, 3H, CH3NHCO), 4.06 (s, 2H, ClCH2CO), 6.63 (br, H,
CONH); 13C(CDCl3): 26.57 (CH3NH), 42.66 (ClCH2), 166.48 (CO);
m/z(FAB) 108.3 (M++1). |
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 | Uiso*/Ueq | |
C1A | 0.7241 (4) | 0.06179 (7) | −0.0569 (3) | 0.0247 (4) | |
H1C | 0.7838 | 0.0310 | −0.1095 | 0.030* | |
H1D | 0.8196 | 0.0908 | −0.0945 | 0.030* | |
C2A | 0.8155 (4) | 0.05780 (7) | 0.1526 (3) | 0.0200 (4) | |
C3A | 0.7112 (4) | 0.05593 (8) | 0.4489 (3) | 0.0301 (5) | |
H3A | 0.7821 | 0.0219 | 0.4844 | 0.045* | |
H3B | 0.5520 | 0.0620 | 0.4955 | 0.045* | |
H3C | 0.8535 | 0.0808 | 0.5028 | 0.045* | |
N1A | 0.6315 (3) | 0.06045 (6) | 0.2480 (2) | 0.0222 (4) | |
O1A | 1.0624 (3) | 0.05209 (6) | 0.2257 (2) | 0.0305 (3) | |
Cl1A | 0.36552 (9) | 0.069495 (19) | −0.15967 (7) | 0.02893 (14) | |
H1A | 0.476 (5) | 0.0620 (8) | 0.193 (3) | 0.028 (6)* | |
C1B | 0.2556 (4) | 0.20093 (7) | −0.1808 (3) | 0.0248 (4) | |
H1E | 0.3703 | 0.1811 | −0.2426 | 0.030* | |
H1F | 0.2851 | 0.2370 | −0.2033 | 0.030* | |
C2B | 0.3550 (4) | 0.19130 (7) | 0.0262 (3) | 0.0211 (4) | |
C3B | 0.2553 (4) | 0.17826 (8) | 0.3214 (3) | 0.0294 (5) | |
H3D | 0.4262 | 0.1590 | 0.3583 | 0.044* | |
H3E | 0.1125 | 0.1600 | 0.3598 | 0.044* | |
H3F | 0.2833 | 0.2114 | 0.3817 | 0.044* | |
N1B | 0.1724 (3) | 0.18466 (6) | 0.1208 (2) | 0.0222 (4) | |
O1B | 0.6031 (3) | 0.19148 (5) | 0.0972 (2) | 0.0291 (3) | |
Cl1B | −0.09421 (9) | 0.186180 (19) | −0.29016 (7) | 0.02920 (15) | |
H1B | 0.013 (4) | 0.1874 (7) | 0.064 (3) | 0.018 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.0179 (9) | 0.0330 (11) | 0.0249 (11) | 0.0012 (8) | 0.0087 (8) | 0.0004 (8) |
C2A | 0.0168 (9) | 0.0193 (9) | 0.0240 (10) | −0.0008 (7) | 0.0056 (8) | 0.0010 (7) |
C3A | 0.0249 (10) | 0.0433 (12) | 0.0221 (11) | 0.0016 (9) | 0.0066 (9) | 0.0010 (9) |
N1A | 0.0142 (8) | 0.0301 (9) | 0.0210 (9) | 0.0012 (6) | 0.0028 (7) | 0.0006 (7) |
O1A | 0.0142 (7) | 0.0476 (9) | 0.0292 (8) | 0.0020 (6) | 0.0051 (6) | 0.0041 (7) |
Cl1A | 0.0189 (2) | 0.0415 (3) | 0.0243 (3) | 0.00423 (19) | 0.00237 (19) | −0.0010 (2) |
C1B | 0.0156 (9) | 0.0342 (11) | 0.0248 (10) | −0.0013 (8) | 0.0058 (8) | 0.0027 (8) |
C2B | 0.0171 (9) | 0.0219 (9) | 0.0237 (10) | 0.0008 (7) | 0.0045 (8) | −0.0029 (7) |
C3B | 0.0249 (11) | 0.0418 (12) | 0.0212 (10) | 0.0005 (9) | 0.0058 (8) | −0.0001 (9) |
N1B | 0.0143 (8) | 0.0317 (9) | 0.0205 (9) | 0.0005 (6) | 0.0044 (7) | −0.0006 (7) |
O1B | 0.0140 (7) | 0.0439 (9) | 0.0288 (8) | 0.0001 (6) | 0.0050 (6) | −0.0030 (6) |
Cl1B | 0.0186 (2) | 0.0440 (3) | 0.0229 (3) | −0.0025 (2) | 0.00221 (19) | 0.0002 (2) |
Geometric parameters (Å, º) top
C1A—C2A | 1.508 (3) | C1B—C2B | 1.509 (3) |
C1A—Cl1A | 1.7851 (19) | C1B—Cl1B | 1.7846 (19) |
C1A—H1C | 0.9900 | C1B—H1E | 0.9900 |
C1A—H1D | 0.9900 | C1B—H1F | 0.9900 |
C2A—O1A | 1.233 (2) | C2B—O1B | 1.227 (2) |
C2A—N1A | 1.326 (2) | C2B—N1B | 1.326 (2) |
C3A—N1A | 1.446 (2) | C3B—N1B | 1.449 (2) |
C3A—H3A | 0.9800 | C3B—H3D | 0.9800 |
C3A—H3B | 0.9800 | C3B—H3E | 0.9800 |
C3A—H3C | 0.9800 | C3B—H3F | 0.9800 |
N1A—H1A | 0.78 (2) | N1B—H1B | 0.81 (2) |
| | | |
C2A—C1A—Cl1A | 116.00 (12) | C2B—C1B—Cl1B | 116.11 (13) |
C2A—C1A—H1C | 108.3 | C2B—C1B—H1E | 108.3 |
Cl1A—C1A—H1C | 108.3 | Cl1B—C1B—H1E | 108.3 |
C2A—C1A—H1D | 108.3 | C2B—C1B—H1F | 108.3 |
Cl1A—C1A—H1D | 108.3 | Cl1B—C1B—H1F | 108.3 |
H1C—C1A—H1D | 107.4 | H1E—C1B—H1F | 107.4 |
O1A—C2A—N1A | 123.65 (18) | O1B—C2B—N1B | 124.08 (18) |
O1A—C2A—C1A | 116.81 (15) | O1B—C2B—C1B | 117.04 (16) |
N1A—C2A—C1A | 119.54 (16) | N1B—C2B—C1B | 118.86 (16) |
N1A—C3A—H3A | 109.5 | N1B—C3B—H3D | 109.5 |
N1A—C3A—H3B | 109.5 | N1B—C3B—H3E | 109.5 |
H3A—C3A—H3B | 109.5 | H3D—C3B—H3E | 109.5 |
N1A—C3A—H3C | 109.5 | N1B—C3B—H3F | 109.5 |
H3A—C3A—H3C | 109.5 | H3D—C3B—H3F | 109.5 |
H3B—C3A—H3C | 109.5 | H3E—C3B—H3F | 109.5 |
C2A—N1A—C3A | 121.05 (16) | C2B—N1B—C3B | 121.31 (16) |
C2A—N1A—H1A | 118.9 (17) | C2B—N1B—H1B | 117.3 (14) |
C3A—N1A—H1A | 119.8 (17) | C3B—N1B—H1B | 121.1 (14) |
| | | |
Cl1A—C1A—C2A—O1A | 179.47 (14) | Cl1B—C1B—C2B—O1B | 165.91 (14) |
Cl1A—C1A—C2A—N1A | −0.4 (2) | Cl1B—C1B—C2B—N1B | −16.0 (2) |
O1A—C2A—N1A—C3A | −0.9 (3) | O1B—C2B—N1B—C3B | 1.7 (3) |
C1A—C2A—N1A—C3A | 178.96 (17) | C1B—C2B—N1B—C3B | −176.29 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O1Ai | 0.78 (2) | 2.20 (2) | 2.865 (2) | 143 (2) |
N1B—H1B···O1Bi | 0.81 (2) | 2.17 (2) | 2.860 (2) | 143.2 (19) |
C1A—H1C···O1Aii | 0.99 | 2.57 | 3.556 (3) | 176 |
C1B—H1F···O1Biii | 0.99 | 2.43 | 3.282 (2) | 144 |
C1B—H1E···Cl1Biv | 0.99 | 2.85 | 3.644 (2) | 138 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y, −z; (iii) x−1/2, −y+1/2, z−1/2; (iv) x+1, y, z. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
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.