The structure of the title compound, C
9H
10ClNO, is closely related to those of 2-chloro-
N-(4-nitrophenyl)acetamide and other related amides. The molecules are linked into zigzag chains through N—H
O hydrogen bonding.
Supporting information
CCDC reference: 613383
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.006 Å
- R factor = 0.097
- wR factor = 0.288
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level B
RINTA01_ALERT_3_B The value of Rint is greater than 0.15
Rint given 0.188
PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.19
Alert level C
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.288
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.87 Sigma
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.75 mm
PLAT084_ALERT_2_C High R2 Value .................................. 0.29
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT731_ALERT_1_C Bond Calc 0.86(3), Rep 0.857(10) ...... 3.00 su-Ra
N5 -H5N 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.86(3), Rep 0.857(10) ...... 3.00 su-Ra
N5 -H5N 1.555 1.555
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 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
5 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: CAD-4 EXPRESS (Nonius, 1996); cell refinement: CAD-4 EXPRESS; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1999); software used to prepare material for publication: SHELXL97.
2-Chloro-
N-(4-methylphenyl)acetamide
top
Crystal data top
C9H10ClNO | Dx = 1.320 Mg m−3 |
Mr = 183.63 | Melting point: 429 K |
Orthorhombic, Pbca | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 25 reflections |
a = 10.585 (2) Å | θ = 12.0–25.2° |
b = 9.262 (4) Å | µ = 3.26 mm−1 |
c = 18.848 (9) Å | T = 299 K |
V = 1847.8 (12) Å3 | Thick needle, colourless |
Z = 8 | 0.75 × 0.18 × 0.18 mm |
F(000) = 768 | |
Data collection top
Nonius CAD-4 diffractometer | Rint = 0.188 |
Radiation source: fine-focus sealed tube | θmax = 66.9°, θmin = 4.7° |
Graphite monochromator | h = −12→4 |
ω/2θ scans | k = 0→11 |
2368 measured reflections | l = 0→22 |
1641 independent reflections | 3 standard reflections every 120 min |
1171 reflections with I > 2σ(I) | intensity decay: 5.2% |
Refinement top
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)] = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.288 | w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.002 |
1641 reflections | Δρmax = 0.50 e Å−3 |
114 parameters | Δρmin = −0.62 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0043 (15) |
Special details top
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 | |
C2 | 0.8045 (4) | −0.0328 (5) | 0.4539 (2) | 0.0699 (11) | |
H2A | 0.7524 | −0.0666 | 0.4150 | 0.084* | |
H2B | 0.8533 | −0.1141 | 0.4713 | 0.084* | |
C3 | 0.7208 (3) | 0.0229 (4) | 0.51257 (17) | 0.0517 (9) | |
C6 | 0.5656 (3) | −0.0758 (4) | 0.59930 (19) | 0.0502 (9) | |
C7 | 0.5195 (4) | −0.2065 (4) | 0.6247 (2) | 0.0612 (10) | |
H7 | 0.5465 | −0.2931 | 0.6048 | 0.073* | |
C8 | 0.4340 (4) | −0.2068 (5) | 0.6793 (2) | 0.0745 (12) | |
H8 | 0.4028 | −0.2947 | 0.6955 | 0.089* | |
C9 | 0.3926 (4) | −0.0812 (6) | 0.7112 (2) | 0.0750 (13) | |
C10 | 0.4388 (4) | 0.0488 (6) | 0.6847 (3) | 0.0760 (13) | |
H10 | 0.4112 | 0.1351 | 0.7045 | 0.091* | |
C11 | 0.5249 (4) | 0.0520 (4) | 0.6294 (2) | 0.0654 (11) | |
H11 | 0.5552 | 0.1399 | 0.6126 | 0.078* | |
C12 | 0.2983 (5) | −0.0817 (9) | 0.7715 (3) | 0.118 (2) | |
H12A | 0.2981 | −0.1749 | 0.7938 | 0.141* | |
H12B | 0.2155 | −0.0611 | 0.7533 | 0.141* | |
H12C | 0.3215 | −0.0094 | 0.8056 | 0.141* | |
N5 | 0.6554 (3) | −0.0844 (3) | 0.54348 (17) | 0.0532 (9) | |
H5N | 0.685 (4) | −0.167 (2) | 0.532 (2) | 0.064* | |
O4 | 0.7113 (3) | 0.1506 (3) | 0.52892 (18) | 0.0780 (10) | |
Cl1 | 0.90783 (14) | 0.10108 (13) | 0.42283 (8) | 0.0953 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.078 (2) | 0.046 (2) | 0.086 (2) | −0.017 (2) | 0.009 (2) | −0.0018 (19) |
C3 | 0.0532 (17) | 0.0340 (19) | 0.0680 (19) | −0.0028 (14) | −0.0102 (15) | −0.0003 (15) |
C6 | 0.0537 (18) | 0.0376 (18) | 0.0592 (18) | 0.0014 (14) | −0.0075 (15) | 0.0015 (13) |
C7 | 0.069 (2) | 0.0420 (19) | 0.072 (2) | −0.0099 (16) | 0.0006 (18) | 0.0032 (16) |
C8 | 0.079 (3) | 0.065 (3) | 0.079 (3) | −0.013 (2) | 0.002 (2) | 0.011 (2) |
C9 | 0.063 (2) | 0.091 (3) | 0.071 (2) | −0.001 (2) | 0.0022 (19) | −0.001 (2) |
C10 | 0.071 (2) | 0.070 (3) | 0.087 (3) | 0.010 (2) | 0.006 (2) | −0.016 (2) |
C11 | 0.071 (2) | 0.0415 (18) | 0.084 (2) | 0.0088 (17) | 0.000 (2) | −0.0030 (18) |
C12 | 0.096 (4) | 0.158 (7) | 0.099 (4) | 0.000 (4) | 0.029 (3) | 0.004 (4) |
N5 | 0.0625 (17) | 0.0272 (15) | 0.0698 (18) | −0.0022 (11) | 0.0006 (15) | −0.0010 (12) |
O4 | 0.090 (2) | 0.0301 (14) | 0.114 (2) | −0.0105 (14) | 0.0136 (18) | −0.0056 (13) |
Cl1 | 0.1033 (11) | 0.0658 (9) | 0.1167 (12) | −0.0212 (6) | 0.0337 (7) | 0.0145 (6) |
Geometric parameters (Å, º) top
C2—C3 | 1.508 (5) | C8—C9 | 1.380 (7) |
C2—Cl1 | 1.754 (4) | C8—H8 | 0.9300 |
C2—H2A | 0.9700 | C9—C10 | 1.392 (7) |
C2—H2B | 0.9700 | C9—C12 | 1.513 (7) |
C3—O4 | 1.226 (5) | C10—C11 | 1.385 (6) |
C3—N5 | 1.344 (4) | C10—H10 | 0.9300 |
C6—C11 | 1.381 (5) | C11—H11 | 0.9300 |
C6—C7 | 1.390 (5) | C12—H12A | 0.9600 |
C6—N5 | 1.420 (5) | C12—H12B | 0.9600 |
C7—C8 | 1.371 (6) | C12—H12C | 0.9600 |
C7—H7 | 0.9300 | N5—H5N | 0.857 (10) |
| | | |
C3—C2—Cl1 | 111.7 (3) | C8—C9—C10 | 117.5 (4) |
C3—C2—H2A | 109.3 | C8—C9—C12 | 122.2 (5) |
Cl1—C2—H2A | 109.3 | C10—C9—C12 | 120.3 (5) |
C3—C2—H2B | 109.3 | C11—C10—C9 | 121.3 (4) |
Cl1—C2—H2B | 109.3 | C11—C10—H10 | 119.3 |
H2A—C2—H2B | 107.9 | C9—C10—H10 | 119.3 |
O4—C3—N5 | 124.2 (3) | C6—C11—C10 | 119.7 (4) |
O4—C3—C2 | 124.2 (3) | C6—C11—H11 | 120.2 |
N5—C3—C2 | 111.6 (3) | C10—C11—H11 | 120.2 |
C11—C6—C7 | 119.7 (4) | C9—C12—H12A | 109.5 |
C11—C6—N5 | 124.1 (3) | C9—C12—H12B | 109.5 |
C7—C6—N5 | 116.1 (3) | H12A—C12—H12B | 109.5 |
C8—C7—C6 | 119.5 (4) | C9—C12—H12C | 109.5 |
C8—C7—H7 | 120.3 | H12A—C12—H12C | 109.5 |
C6—C7—H7 | 120.3 | H12B—C12—H12C | 109.5 |
C7—C8—C9 | 122.3 (4) | C3—N5—C6 | 128.6 (3) |
C7—C8—H8 | 118.8 | C3—N5—H5N | 111 (3) |
C9—C8—H8 | 118.8 | C6—N5—H5N | 119 (3) |
| | | |
Cl1—C2—C3—O4 | 10.9 (5) | C12—C9—C10—C11 | −179.9 (4) |
Cl1—C2—C3—N5 | −170.7 (3) | C7—C6—C11—C10 | 0.1 (6) |
C11—C6—C7—C8 | 0.1 (6) | N5—C6—C11—C10 | −178.7 (4) |
N5—C6—C7—C8 | 179.0 (3) | C9—C10—C11—C6 | 0.5 (6) |
C6—C7—C8—C9 | −0.9 (6) | O4—C3—N5—C6 | −0.3 (6) |
C7—C8—C9—C10 | 1.5 (7) | C2—C3—N5—C6 | −178.7 (3) |
C7—C8—C9—C12 | −179.9 (4) | C11—C6—N5—C3 | 3.7 (6) |
C8—C9—C10—C11 | −1.2 (7) | C7—C6—N5—C3 | −175.1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O4i | 0.86 (1) | 2.01 (2) | 2.845 (4) | 163 (4) |
Symmetry code: (i) −x+3/2, y−1/2, z. |