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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807009956/bg2032sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807009956/bg2032Isup2.hkl
Contains datablock I

CCDC reference: 642905

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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

Computing details top

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
C3H6ClNOF(000) = 448
Mr = 107.54Dx = 1.475 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2696 reflections
a = 5.0911 (3) Åθ = 2.9–28.2°
b = 26.5090 (17) ŵ = 0.64 mm1
c = 7.4671 (5) ÅT = 173 K
β = 106.103 (2)°Needle, colourless
V = 968.22 (11) Å30.32 × 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 tubeRint = 0.061
Graphite monochromatorθmax = 28.0°, θmin = 1.5°
φ and ω scansh = 66
10450 measured reflectionsk = 3335
2338 independent reflectionsl = 99
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H 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 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.27 e Å3
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
xyzUiso*/Ueq
C1A0.7241 (4)0.06179 (7)0.0569 (3)0.0247 (4)
H1C0.78380.03100.10950.030*
H1D0.81960.09080.09450.030*
C2A0.8155 (4)0.05780 (7)0.1526 (3)0.0200 (4)
C3A0.7112 (4)0.05593 (8)0.4489 (3)0.0301 (5)
H3A0.78210.02190.48440.045*
H3B0.55200.06200.49550.045*
H3C0.85350.08080.50280.045*
N1A0.6315 (3)0.06045 (6)0.2480 (2)0.0222 (4)
O1A1.0624 (3)0.05209 (6)0.2257 (2)0.0305 (3)
Cl1A0.36552 (9)0.069495 (19)0.15967 (7)0.02893 (14)
H1A0.476 (5)0.0620 (8)0.193 (3)0.028 (6)*
C1B0.2556 (4)0.20093 (7)0.1808 (3)0.0248 (4)
H1E0.37030.18110.24260.030*
H1F0.28510.23700.20330.030*
C2B0.3550 (4)0.19130 (7)0.0262 (3)0.0211 (4)
C3B0.2553 (4)0.17826 (8)0.3214 (3)0.0294 (5)
H3D0.42620.15900.35830.044*
H3E0.11250.16000.35980.044*
H3F0.28330.21140.38170.044*
N1B0.1724 (3)0.18466 (6)0.1208 (2)0.0222 (4)
O1B0.6031 (3)0.19148 (5)0.0972 (2)0.0291 (3)
Cl1B0.09421 (9)0.186180 (19)0.29016 (7)0.02920 (15)
H1B0.013 (4)0.1874 (7)0.064 (3)0.018 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0179 (9)0.0330 (11)0.0249 (11)0.0012 (8)0.0087 (8)0.0004 (8)
C2A0.0168 (9)0.0193 (9)0.0240 (10)0.0008 (7)0.0056 (8)0.0010 (7)
C3A0.0249 (10)0.0433 (12)0.0221 (11)0.0016 (9)0.0066 (9)0.0010 (9)
N1A0.0142 (8)0.0301 (9)0.0210 (9)0.0012 (6)0.0028 (7)0.0006 (7)
O1A0.0142 (7)0.0476 (9)0.0292 (8)0.0020 (6)0.0051 (6)0.0041 (7)
Cl1A0.0189 (2)0.0415 (3)0.0243 (3)0.00423 (19)0.00237 (19)0.0010 (2)
C1B0.0156 (9)0.0342 (11)0.0248 (10)0.0013 (8)0.0058 (8)0.0027 (8)
C2B0.0171 (9)0.0219 (9)0.0237 (10)0.0008 (7)0.0045 (8)0.0029 (7)
C3B0.0249 (11)0.0418 (12)0.0212 (10)0.0005 (9)0.0058 (8)0.0001 (9)
N1B0.0143 (8)0.0317 (9)0.0205 (9)0.0005 (6)0.0044 (7)0.0006 (7)
O1B0.0140 (7)0.0439 (9)0.0288 (8)0.0001 (6)0.0050 (6)0.0030 (6)
Cl1B0.0186 (2)0.0440 (3)0.0229 (3)0.0025 (2)0.00221 (19)0.0002 (2)
Geometric parameters (Å, º) top
C1A—C2A1.508 (3)C1B—C2B1.509 (3)
C1A—Cl1A1.7851 (19)C1B—Cl1B1.7846 (19)
C1A—H1C0.9900C1B—H1E0.9900
C1A—H1D0.9900C1B—H1F0.9900
C2A—O1A1.233 (2)C2B—O1B1.227 (2)
C2A—N1A1.326 (2)C2B—N1B1.326 (2)
C3A—N1A1.446 (2)C3B—N1B1.449 (2)
C3A—H3A0.9800C3B—H3D0.9800
C3A—H3B0.9800C3B—H3E0.9800
C3A—H3C0.9800C3B—H3F0.9800
N1A—H1A0.78 (2)N1B—H1B0.81 (2)
C2A—C1A—Cl1A116.00 (12)C2B—C1B—Cl1B116.11 (13)
C2A—C1A—H1C108.3C2B—C1B—H1E108.3
Cl1A—C1A—H1C108.3Cl1B—C1B—H1E108.3
C2A—C1A—H1D108.3C2B—C1B—H1F108.3
Cl1A—C1A—H1D108.3Cl1B—C1B—H1F108.3
H1C—C1A—H1D107.4H1E—C1B—H1F107.4
O1A—C2A—N1A123.65 (18)O1B—C2B—N1B124.08 (18)
O1A—C2A—C1A116.81 (15)O1B—C2B—C1B117.04 (16)
N1A—C2A—C1A119.54 (16)N1B—C2B—C1B118.86 (16)
N1A—C3A—H3A109.5N1B—C3B—H3D109.5
N1A—C3A—H3B109.5N1B—C3B—H3E109.5
H3A—C3A—H3B109.5H3D—C3B—H3E109.5
N1A—C3A—H3C109.5N1B—C3B—H3F109.5
H3A—C3A—H3C109.5H3D—C3B—H3F109.5
H3B—C3A—H3C109.5H3E—C3B—H3F109.5
C2A—N1A—C3A121.05 (16)C2B—N1B—C3B121.31 (16)
C2A—N1A—H1A118.9 (17)C2B—N1B—H1B117.3 (14)
C3A—N1A—H1A119.8 (17)C3B—N1B—H1B121.1 (14)
Cl1A—C1A—C2A—O1A179.47 (14)Cl1B—C1B—C2B—O1B165.91 (14)
Cl1A—C1A—C2A—N1A0.4 (2)Cl1B—C1B—C2B—N1B16.0 (2)
O1A—C2A—N1A—C3A0.9 (3)O1B—C2B—N1B—C3B1.7 (3)
C1A—C2A—N1A—C3A178.96 (17)C1B—C2B—N1B—C3B176.29 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O1Ai0.78 (2)2.20 (2)2.865 (2)143 (2)
N1B—H1B···O1Bi0.81 (2)2.17 (2)2.860 (2)143.2 (19)
C1A—H1C···O1Aii0.992.573.556 (3)176
C1B—H1F···O1Biii0.992.433.282 (2)144
C1B—H1E···Cl1Biv0.992.853.644 (2)138
Symmetry codes: (i) x1, y, z; (ii) x+2, y, z; (iii) x1/2, y+1/2, z1/2; (iv) x+1, y, z.
 

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