Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053366/hg2321sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053366/hg2321Isup2.hkl |
CCDC reference: 672815
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.095
- Data-to-parameter ratio = 21.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT410_ALERT_2_C Short Intra H...H Contact H7 .. H14A .. 1.95 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.86 From the CIF: _reflns_number_total 3363 Count of symmetry unique reflns 1927 Completeness (_total/calc) 174.52% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1436 Fraction of Friedel pairs measured 0.745 Are heavy atom types Z>Si present yes PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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
For related literature, see: Allen et al. (1987); Wen et al. (2005); Wen, Li et al. (2006); Wen, Zhang et al. (2006); Zhang, Wen et al. (2006); Zhang, Xu et al. (2006).
Chloroacetyl chloride (5.65 g, 0.05 mol) was added to a solution of N,N-dicyclohexylamine (9.05 g, 0.05 mol) and triethylamine (5.1 g, 0.05 mol) in benzene (60 ml) over a period of 40 min, with cooling in an ice bath, and then the mixture was stirred at room remperature for 5 h. After separation of the triethylamine hydrochloride by filtration, the organic phase was washed three times with water. The benzene layer was removed and evaporated. The title compound was obtained after drying the colorless powder at room temperature for 48 h. Colourless single cystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution over a period of 8 d.
H atoms were positioned geometrically, with N—H = 0.86 Å and C—H = 0.95–0.99 Å, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2 Ueq(C,N).
Data collection: SMART (Bruker 2001); cell refinement: SAINT (Bruker 2001); data reduction: SAINT (Bruker 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).
C14H24ClNO | F(000) = 560 |
Mr = 257.79 | Dx = 1.213 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3915 reflections |
a = 10.339 (2) Å | θ = 2.5–27.9° |
b = 11.051 (2) Å | µ = 0.26 mm−1 |
c = 12.358 (3) Å | T = 113 K |
V = 1412.1 (5) Å3 | Column, colourless |
Z = 4 | 0.08 × 0.06 × 0.04 mm |
Bruker SMART CCD area-detector diffractometer | 3363 independent reflections |
Radiation source: fine-focus sealed tube | 3079 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
ϕ and ω scans | θmax = 27.9°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.980, Tmax = 0.990 | k = −14→14 |
17892 measured reflections | l = −16→16 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0571P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3363 reflections | Δρmax = 0.18 e Å−3 |
154 parameters | Δρmin = −0.28 e Å−3 |
0 restraints | Absolute structure: Flack (1983), with 1436 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (6) |
C14H24ClNO | V = 1412.1 (5) Å3 |
Mr = 257.79 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 10.339 (2) Å | µ = 0.26 mm−1 |
b = 11.051 (2) Å | T = 113 K |
c = 12.358 (3) Å | 0.08 × 0.06 × 0.04 mm |
Bruker SMART CCD area-detector diffractometer | 3363 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3079 reflections with I > 2σ(I) |
Tmin = 0.980, Tmax = 0.990 | Rint = 0.047 |
17892 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.095 | Δρmax = 0.18 e Å−3 |
S = 1.02 | Δρmin = −0.28 e Å−3 |
3363 reflections | Absolute structure: Flack (1983), with 1436 Friedel pairs |
154 parameters | Absolute structure parameter: 0.01 (6) |
0 restraints |
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 | ||
Cl1 | 0.05746 (5) | 0.20328 (5) | 0.33226 (4) | 0.03999 (15) | |
O1 | −0.10518 (11) | 0.25868 (10) | 0.57080 (11) | 0.0253 (3) | |
N1 | 0.03499 (12) | 0.10126 (12) | 0.59095 (10) | 0.0172 (3) | |
C1 | −0.04307 (15) | 0.04407 (14) | 0.67755 (12) | 0.0173 (3) | |
H1 | 0.0069 | −0.0261 | 0.7021 | 0.021* | |
C2 | −0.17229 (16) | −0.00591 (15) | 0.63806 (13) | 0.0194 (3) | |
H2A | −0.1581 | −0.0584 | 0.5763 | 0.023* | |
H2B | −0.2276 | 0.0603 | 0.6153 | 0.023* | |
C3 | −0.23877 (16) | −0.07731 (15) | 0.72882 (14) | 0.0219 (4) | |
H3A | −0.3231 | −0.1042 | 0.7043 | 0.026* | |
H3B | −0.1877 | −0.1484 | 0.7459 | 0.026* | |
C4 | −0.25466 (17) | −0.00027 (16) | 0.83032 (15) | 0.0244 (4) | |
H4A | −0.3142 | 0.0656 | 0.8156 | 0.029* | |
H4B | −0.2912 | −0.0493 | 0.8878 | 0.029* | |
C5 | −0.12543 (17) | 0.05114 (16) | 0.86687 (14) | 0.0245 (4) | |
H5A | −0.0689 | −0.0147 | 0.8883 | 0.029* | |
H5B | −0.1388 | 0.1026 | 0.9294 | 0.029* | |
C6 | −0.06063 (17) | 0.12441 (15) | 0.77701 (13) | 0.0219 (4) | |
H6A | −0.1138 | 0.1938 | 0.7587 | 0.026* | |
H6B | 0.0228 | 0.1537 | 0.8015 | 0.026* | |
C7 | 0.14973 (16) | 0.03393 (14) | 0.55313 (14) | 0.0185 (3) | |
H7 | 0.1866 | 0.0804 | 0.4930 | 0.022* | |
C8 | 0.25475 (16) | 0.02467 (16) | 0.63952 (15) | 0.0235 (4) | |
H8A | 0.2224 | −0.0204 | 0.7012 | 0.028* | |
H8B | 0.2787 | 0.1050 | 0.6640 | 0.028* | |
C9 | 0.37321 (17) | −0.03934 (16) | 0.59224 (17) | 0.0281 (4) | |
H9A | 0.4093 | 0.0096 | 0.5345 | 0.034* | |
H9B | 0.4386 | −0.0478 | 0.6480 | 0.034* | |
C10 | 0.33861 (18) | −0.16382 (16) | 0.54811 (16) | 0.0301 (4) | |
H10A | 0.4148 | −0.2007 | 0.5163 | 0.036* | |
H10B | 0.3093 | −0.2152 | 0.6068 | 0.036* | |
C11 | 0.23278 (19) | −0.15410 (17) | 0.46302 (15) | 0.0298 (4) | |
H11A | 0.2092 | −0.2345 | 0.4386 | 0.036* | |
H11B | 0.2652 | −0.1093 | 0.4012 | 0.036* | |
C12 | 0.11336 (17) | −0.09055 (15) | 0.50785 (14) | 0.0228 (4) | |
H12A | 0.0753 | −0.1395 | 0.5647 | 0.027* | |
H12B | 0.0497 | −0.0811 | 0.4508 | 0.027* | |
C13 | −0.00411 (15) | 0.20666 (15) | 0.54622 (13) | 0.0187 (3) | |
C14 | 0.08384 (16) | 0.26703 (14) | 0.46292 (14) | 0.0217 (4) | |
H14A | 0.1735 | 0.2559 | 0.4837 | 0.026* | |
H14B | 0.0663 | 0.3532 | 0.4608 | 0.026* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0399 (3) | 0.0581 (3) | 0.0220 (2) | −0.0139 (2) | −0.0001 (2) | 0.0024 (2) |
O1 | 0.0185 (6) | 0.0240 (6) | 0.0336 (7) | 0.0053 (5) | 0.0043 (5) | 0.0066 (5) |
N1 | 0.0148 (7) | 0.0173 (7) | 0.0196 (6) | 0.0019 (5) | 0.0044 (6) | 0.0026 (5) |
C1 | 0.0172 (8) | 0.0171 (8) | 0.0175 (7) | 0.0006 (6) | 0.0015 (7) | 0.0026 (6) |
C2 | 0.0187 (8) | 0.0229 (8) | 0.0166 (8) | −0.0003 (6) | −0.0002 (7) | −0.0010 (7) |
C3 | 0.0214 (9) | 0.0230 (9) | 0.0215 (8) | −0.0039 (7) | 0.0037 (7) | −0.0001 (7) |
C4 | 0.0245 (9) | 0.0275 (9) | 0.0211 (8) | −0.0037 (7) | 0.0073 (8) | −0.0006 (8) |
C5 | 0.0290 (10) | 0.0278 (9) | 0.0165 (8) | 0.0002 (7) | 0.0020 (7) | −0.0017 (7) |
C6 | 0.0208 (8) | 0.0257 (9) | 0.0191 (7) | −0.0024 (7) | 0.0004 (7) | −0.0035 (7) |
C7 | 0.0168 (8) | 0.0174 (8) | 0.0214 (8) | 0.0015 (6) | 0.0038 (7) | 0.0005 (7) |
C8 | 0.0159 (8) | 0.0227 (9) | 0.0320 (10) | −0.0004 (6) | −0.0003 (7) | −0.0005 (7) |
C9 | 0.0183 (9) | 0.0251 (9) | 0.0408 (11) | 0.0041 (7) | 0.0035 (8) | 0.0068 (8) |
C10 | 0.0278 (10) | 0.0243 (9) | 0.0381 (11) | 0.0083 (8) | 0.0114 (9) | 0.0065 (8) |
C11 | 0.0410 (11) | 0.0219 (9) | 0.0264 (10) | 0.0066 (8) | 0.0119 (9) | −0.0019 (7) |
C12 | 0.0253 (9) | 0.0211 (8) | 0.0221 (8) | −0.0003 (7) | 0.0012 (7) | −0.0017 (7) |
C13 | 0.0159 (8) | 0.0195 (8) | 0.0206 (8) | −0.0006 (6) | −0.0007 (6) | 0.0018 (7) |
C14 | 0.0218 (9) | 0.0182 (8) | 0.0250 (9) | 0.0004 (6) | 0.0017 (7) | 0.0033 (7) |
Cl1—C14 | 1.7827 (18) | C6—H6B | 0.9700 |
O1—C13 | 1.2308 (19) | C7—C8 | 1.526 (2) |
N1—C13 | 1.351 (2) | C7—C12 | 1.532 (2) |
N1—C7 | 1.476 (2) | C7—H7 | 0.9800 |
N1—C1 | 1.4819 (19) | C8—C9 | 1.530 (2) |
C1—C2 | 1.526 (2) | C8—H8A | 0.9700 |
C1—C6 | 1.527 (2) | C8—H8B | 0.9700 |
C1—H1 | 0.9800 | C9—C10 | 1.522 (3) |
C2—C3 | 1.534 (2) | C9—H9A | 0.9700 |
C2—H2A | 0.9700 | C9—H9B | 0.9700 |
C2—H2B | 0.9700 | C10—C11 | 1.521 (3) |
C3—C4 | 1.525 (2) | C10—H10A | 0.9700 |
C3—H3A | 0.9700 | C10—H10B | 0.9700 |
C3—H3B | 0.9700 | C11—C12 | 1.525 (3) |
C4—C5 | 1.521 (2) | C11—H11A | 0.9700 |
C4—H4A | 0.9700 | C11—H11B | 0.9700 |
C4—H4B | 0.9700 | C12—H12A | 0.9700 |
C5—C6 | 1.529 (2) | C12—H12B | 0.9700 |
C5—H5A | 0.9700 | C13—C14 | 1.527 (2) |
C5—H5B | 0.9700 | C14—H14A | 0.9700 |
C6—H6A | 0.9700 | C14—H14B | 0.9700 |
C13—N1—C7 | 123.05 (13) | N1—C7—H7 | 106.8 |
C13—N1—C1 | 120.01 (13) | C8—C7—H7 | 106.8 |
C7—N1—C1 | 116.83 (13) | C12—C7—H7 | 106.8 |
N1—C1—C2 | 113.59 (13) | C7—C8—C9 | 109.47 (15) |
N1—C1—C6 | 113.46 (13) | C7—C8—H8A | 109.8 |
C2—C1—C6 | 111.34 (13) | C9—C8—H8A | 109.8 |
N1—C1—H1 | 105.9 | C7—C8—H8B | 109.8 |
C2—C1—H1 | 105.9 | C9—C8—H8B | 109.8 |
C6—C1—H1 | 105.9 | H8A—C8—H8B | 108.2 |
C1—C2—C3 | 110.16 (13) | C10—C9—C8 | 111.50 (15) |
C1—C2—H2A | 109.6 | C10—C9—H9A | 109.3 |
C3—C2—H2A | 109.6 | C8—C9—H9A | 109.3 |
C1—C2—H2B | 109.6 | C10—C9—H9B | 109.3 |
C3—C2—H2B | 109.6 | C8—C9—H9B | 109.3 |
H2A—C2—H2B | 108.1 | H9A—C9—H9B | 108.0 |
C4—C3—C2 | 111.26 (14) | C11—C10—C9 | 110.66 (15) |
C4—C3—H3A | 109.4 | C11—C10—H10A | 109.5 |
C2—C3—H3A | 109.4 | C9—C10—H10A | 109.5 |
C4—C3—H3B | 109.4 | C11—C10—H10B | 109.5 |
C2—C3—H3B | 109.4 | C9—C10—H10B | 109.5 |
H3A—C3—H3B | 108.0 | H10A—C10—H10B | 108.1 |
C5—C4—C3 | 111.00 (14) | C10—C11—C12 | 111.34 (15) |
C5—C4—H4A | 109.4 | C10—C11—H11A | 109.4 |
C3—C4—H4A | 109.4 | C12—C11—H11A | 109.4 |
C5—C4—H4B | 109.4 | C10—C11—H11B | 109.4 |
C3—C4—H4B | 109.4 | C12—C11—H11B | 109.4 |
H4A—C4—H4B | 108.0 | H11A—C11—H11B | 108.0 |
C4—C5—C6 | 111.54 (14) | C11—C12—C7 | 110.34 (15) |
C4—C5—H5A | 109.3 | C11—C12—H12A | 109.6 |
C6—C5—H5A | 109.3 | C7—C12—H12A | 109.6 |
C4—C5—H5B | 109.3 | C11—C12—H12B | 109.6 |
C6—C5—H5B | 109.3 | C7—C12—H12B | 109.6 |
H5A—C5—H5B | 108.0 | H12A—C12—H12B | 108.1 |
C1—C6—C5 | 109.20 (13) | O1—C13—N1 | 123.76 (15) |
C1—C6—H6A | 109.8 | O1—C13—C14 | 117.90 (15) |
C5—C6—H6A | 109.8 | N1—C13—C14 | 118.31 (14) |
C1—C6—H6B | 109.8 | C13—C14—Cl1 | 110.29 (12) |
C5—C6—H6B | 109.8 | C13—C14—H14A | 109.6 |
H6A—C6—H6B | 108.3 | Cl1—C14—H14A | 109.6 |
N1—C7—C8 | 112.58 (13) | C13—C14—H14B | 109.6 |
N1—C7—C12 | 111.78 (13) | Cl1—C14—H14B | 109.6 |
C8—C7—C12 | 111.71 (14) | H14A—C14—H14B | 108.1 |
C13—N1—C1—C2 | 69.27 (18) | C1—N1—C7—C12 | 59.52 (18) |
C7—N1—C1—C2 | −107.01 (15) | N1—C7—C8—C9 | −176.61 (13) |
C13—N1—C1—C6 | −59.22 (19) | C12—C7—C8—C9 | 56.66 (18) |
C7—N1—C1—C6 | 124.51 (15) | C7—C8—C9—C10 | −56.9 (2) |
N1—C1—C2—C3 | 172.81 (13) | C8—C9—C10—C11 | 57.0 (2) |
C6—C1—C2—C3 | −57.63 (18) | C9—C10—C11—C12 | −56.2 (2) |
C1—C2—C3—C4 | 55.47 (19) | C10—C11—C12—C7 | 55.71 (19) |
C2—C3—C4—C5 | −55.04 (19) | N1—C7—C12—C11 | 176.38 (14) |
C3—C4—C5—C6 | 56.40 (19) | C8—C7—C12—C11 | −56.45 (18) |
N1—C1—C6—C5 | −172.10 (12) | C7—N1—C13—O1 | 173.80 (15) |
C2—C1—C6—C5 | 58.27 (18) | C1—N1—C13—O1 | −2.2 (2) |
C4—C5—C6—C1 | −57.46 (19) | C7—N1—C13—C14 | −8.2 (2) |
C13—N1—C7—C8 | 116.68 (17) | C1—N1—C13—C14 | 175.78 (14) |
C1—N1—C7—C8 | −67.17 (17) | O1—C13—C14—Cl1 | −98.04 (16) |
C13—N1—C7—C12 | −116.62 (16) | N1—C13—C14—Cl1 | 83.83 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14A···O1i | 0.97 | 2.39 | 3.255 (2) | 148 |
Symmetry code: (i) x+1/2, −y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C14H24ClNO |
Mr | 257.79 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 113 |
a, b, c (Å) | 10.339 (2), 11.051 (2), 12.358 (3) |
V (Å3) | 1412.1 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.08 × 0.06 × 0.04 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.980, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17892, 3363, 3079 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.095, 1.02 |
No. of reflections | 3363 |
No. of parameters | 154 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.28 |
Absolute structure | Flack (1983), with 1436 Friedel pairs |
Absolute structure parameter | 0.01 (6) |
Computer programs: SMART (Bruker 2001), SAINT (Bruker 2001), SHELXTL (Sheldrick, 2001).
Cl1—C14 | 1.7827 (18) | N1—C7 | 1.476 (2) |
O1—C13 | 1.2308 (19) | C13—C14 | 1.527 (2) |
N1—C13 | 1.351 (2) | ||
C13—N1—C7 | 123.05 (13) | N1—C1—C2 | 113.59 (13) |
C13—N1—C1 | 120.01 (13) | N1—C1—C6 | 113.46 (13) |
C7—N1—C1 | 116.83 (13) | C2—C1—C6 | 111.34 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14A···O1i | 0.97 | 2.39 | 3.255 (2) | 148.1 |
Symmetry code: (i) x+1/2, −y+1/2, −z+1. |
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N-Substituted-2-chloroacetamides are important intermediates in organic synthesis. They can be used in the synthesis of many derivatives such as (quinolin-8-yl-oxy)acetamide (Zhang, Xu et al., 2006), 2,5-piperazinedione (Wen, Zhang et al., 2006) and 2,2-(1,3,4- thiadiazolyl-2,5-dithio)diacetamide (Wen et al., 2005). Here, we have synthesized and carried out the structure determination of the title compound, (I) (Fig. 1), a new N,N-disubstituted-2- chloroacetamide.
In the molecule of (I), the bond lengths and angles (Table 1) are within normal ranges (Allen et al., 1987), and comparable to those of the related compounds, 2-chloro-N-(4-nitrophenyl)acetamide (Wen, Li et al., 2006), and 2-chloro-N-(4-ethoxyphenyl)acetamide (Zhang, Wen et al., 2006). The C1/C7/C13/N1 andN1/C1/C14/O1 units are planar, with the dihedral angle between them 4.12 (2)°. The geometries of two cyclohexyl groups are the normal chair conformations. The crystal packing is stabilized by C9—H9···Cl short-contact interactions (Fig. 2).