The structure of the title compound, C
11H
14ClNO, is closely related to the ring-unsubstituted 2,2,2-trimethyl-
N-phenylacetamide and 2,2,2-trimethyl-
N-(4-methylphenyl)acetamide with slightly different bond parameters. The molecules are linked into chains running along the
b-axis direction through N—H
O hydrogen bonding.
Supporting information
CCDC reference: 613410
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.133
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.13
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.77 mm
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 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-PC (Nonius, 1996); cell refinement: CAD-4-PC; 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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
N-(4-chlorophenyl)-2,2,2-trimethylacetamide
top
Crystal data top
C11H14ClNO | F(000) = 896 |
Mr = 211.68 | Dx = 1.218 Mg m−3 |
Orthorhombic, Pbca | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 25 reflections |
a = 9.6933 (6) Å | θ = 9.9–23.9° |
b = 10.115 (1) Å | µ = 2.67 mm−1 |
c = 23.542 (1) Å | T = 299 K |
V = 2308.2 (3) Å3 | Long prism, colourless |
Z = 8 | 0.77 × 0.25 × 0.17 mm |
Data collection top
Nonius CAD-4 diffractometer | 1730 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.016 |
Graphite monochromator | θmax = 67.0°, θmin = 3.8° |
ω/2θ scans | h = −11→1 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→12 |
Tmin = 0.555, Tmax = 0.661 | l = 0→28 |
2104 measured reflections | 3 standard reflections every 120 min |
2061 independent reflections | intensity decay: 1.0% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0758P)2 + 0.5702P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.010 |
2061 reflections | Δρmax = 0.25 e Å−3 |
143 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0087 (7) |
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 | |
C1 | 0.9921 (2) | 0.0451 (3) | 0.35107 (14) | 0.0814 (8) | |
H1A | 1.0764 | 0.0658 | 0.3316 | 0.098* | |
H1B | 1.0118 | −0.0105 | 0.3831 | 0.098* | |
H1C | 0.9493 | 0.1253 | 0.3639 | 0.098* | |
C2 | 0.8608 (3) | 0.0602 (2) | 0.25991 (11) | 0.0738 (7) | |
H2A | 0.9435 | 0.0779 | 0.2388 | 0.089* | |
H2B | 0.8220 | 0.1421 | 0.2730 | 0.089* | |
H2C | 0.7954 | 0.0158 | 0.2360 | 0.089* | |
C3 | 0.9623 (3) | −0.1533 (2) | 0.28933 (13) | 0.0802 (8) | |
H3A | 1.0405 | −0.1314 | 0.2661 | 0.096* | |
H3B | 0.8969 | −0.2028 | 0.2673 | 0.096* | |
H3C | 0.9920 | −0.2055 | 0.3211 | 0.096* | |
C4 | 0.89495 (19) | −0.02701 (16) | 0.31066 (8) | 0.0480 (5) | |
C5 | 0.76262 (19) | −0.06185 (15) | 0.34260 (7) | 0.0406 (4) | |
C8 | 0.56321 (18) | 0.03614 (15) | 0.39263 (7) | 0.0404 (4) | |
C9 | 0.4679 (2) | −0.06468 (18) | 0.38741 (8) | 0.0483 (5) | |
H9 | 0.486 (2) | −0.133 (2) | 0.3630 (10) | 0.058* | |
C10 | 0.3480 (2) | −0.0633 (2) | 0.41907 (9) | 0.0546 (5) | |
H10 | 0.281 (2) | −0.137 (2) | 0.4152 (9) | 0.065* | |
C11 | 0.32368 (19) | 0.0394 (2) | 0.45614 (8) | 0.0525 (5) | |
C12 | 0.4165 (2) | 0.1411 (2) | 0.46181 (8) | 0.0543 (5) | |
H12 | 0.399 (3) | 0.207 (2) | 0.4873 (9) | 0.065* | |
C13 | 0.5365 (2) | 0.13953 (18) | 0.43021 (8) | 0.0501 (5) | |
H13 | 0.606 (2) | 0.205 (2) | 0.4340 (9) | 0.060* | |
N7 | 0.68600 (16) | 0.04180 (14) | 0.36045 (7) | 0.0446 (4) | |
H7N | 0.716 (2) | 0.119 (2) | 0.3558 (8) | 0.053* | |
O6 | 0.72797 (14) | −0.17632 (11) | 0.35204 (6) | 0.0561 (4) | |
Cl14 | 0.17337 (6) | 0.03893 (8) | 0.49664 (3) | 0.0797 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0466 (13) | 0.0940 (18) | 0.104 (2) | −0.0056 (11) | 0.0050 (12) | −0.0238 (15) |
C2 | 0.0829 (16) | 0.0655 (13) | 0.0729 (15) | −0.0031 (12) | 0.0249 (13) | 0.0158 (11) |
C3 | 0.0817 (15) | 0.0456 (11) | 0.113 (2) | 0.0091 (10) | 0.0481 (15) | −0.0030 (12) |
C4 | 0.0486 (10) | 0.0335 (9) | 0.0620 (11) | −0.0007 (7) | 0.0134 (8) | −0.0026 (8) |
C5 | 0.0452 (9) | 0.0292 (8) | 0.0475 (9) | 0.0005 (6) | 0.0036 (7) | 0.0001 (7) |
C8 | 0.0426 (9) | 0.0336 (8) | 0.0451 (9) | 0.0049 (7) | 0.0021 (7) | 0.0026 (7) |
C9 | 0.0478 (10) | 0.0408 (9) | 0.0563 (10) | −0.0013 (8) | 0.0049 (8) | −0.0085 (8) |
C10 | 0.0453 (10) | 0.0550 (11) | 0.0634 (12) | −0.0046 (9) | 0.0033 (9) | −0.0042 (9) |
C11 | 0.0418 (10) | 0.0659 (12) | 0.0497 (10) | 0.0105 (8) | 0.0026 (8) | 0.0003 (9) |
C12 | 0.0546 (11) | 0.0526 (11) | 0.0558 (11) | 0.0123 (9) | 0.0034 (9) | −0.0125 (9) |
C13 | 0.0514 (10) | 0.0378 (9) | 0.0612 (11) | 0.0029 (8) | 0.0023 (9) | −0.0083 (8) |
N7 | 0.0496 (9) | 0.0255 (7) | 0.0586 (9) | −0.0004 (6) | 0.0117 (7) | 0.0009 (6) |
O6 | 0.0562 (8) | 0.0249 (6) | 0.0871 (10) | 0.0000 (5) | 0.0169 (7) | 0.0025 (6) |
Cl14 | 0.0502 (4) | 0.1130 (6) | 0.0761 (4) | 0.0056 (3) | 0.0184 (2) | −0.0134 (3) |
Geometric parameters (Å, º) top
C1—C4 | 1.524 (3) | C5—N7 | 1.352 (2) |
C1—H1A | 0.9600 | C8—C9 | 1.382 (3) |
C1—H1B | 0.9600 | C8—C13 | 1.394 (2) |
C1—H1C | 0.9600 | C8—N7 | 1.412 (2) |
C2—C4 | 1.522 (3) | C9—C10 | 1.381 (3) |
C2—H2A | 0.9600 | C9—H9 | 0.92 (2) |
C2—H2B | 0.9600 | C10—C11 | 1.377 (3) |
C2—H2C | 0.9600 | C10—H10 | 1.00 (2) |
C3—C4 | 1.520 (3) | C11—C12 | 1.373 (3) |
C3—H3A | 0.9600 | C11—Cl14 | 1.7413 (19) |
C3—H3B | 0.9600 | C12—C13 | 1.381 (3) |
C3—H3C | 0.9600 | C12—H12 | 0.91 (2) |
C4—C5 | 1.528 (2) | C13—H13 | 0.95 (2) |
C5—O6 | 1.226 (2) | N7—H7N | 0.84 (2) |
| | | |
C4—C1—H1A | 109.5 | O6—C5—N7 | 121.71 (16) |
C4—C1—H1B | 109.5 | O6—C5—C4 | 122.48 (15) |
H1A—C1—H1B | 109.5 | N7—C5—C4 | 115.81 (14) |
C4—C1—H1C | 109.5 | C9—C8—C13 | 119.08 (17) |
H1A—C1—H1C | 109.5 | C9—C8—N7 | 123.09 (15) |
H1B—C1—H1C | 109.5 | C13—C8—N7 | 117.81 (16) |
C4—C2—H2A | 109.5 | C10—C9—C8 | 120.50 (17) |
C4—C2—H2B | 109.5 | C10—C9—H9 | 120.3 (14) |
H2A—C2—H2B | 109.5 | C8—C9—H9 | 119.2 (14) |
C4—C2—H2C | 109.5 | C11—C10—C9 | 119.58 (19) |
H2A—C2—H2C | 109.5 | C11—C10—H10 | 120.8 (13) |
H2B—C2—H2C | 109.5 | C9—C10—H10 | 119.6 (13) |
C4—C3—H3A | 109.5 | C12—C11—C10 | 120.98 (18) |
C4—C3—H3B | 109.5 | C12—C11—Cl14 | 119.83 (15) |
H3A—C3—H3B | 109.5 | C10—C11—Cl14 | 119.19 (16) |
C4—C3—H3C | 109.5 | C11—C12—C13 | 119.39 (18) |
H3A—C3—H3C | 109.5 | C11—C12—H12 | 119.1 (16) |
H3B—C3—H3C | 109.5 | C13—C12—H12 | 121.5 (16) |
C3—C4—C2 | 108.74 (18) | C12—C13—C8 | 120.47 (18) |
C3—C4—C1 | 110.05 (19) | C12—C13—H13 | 122.6 (13) |
C2—C4—C1 | 110.3 (2) | C8—C13—H13 | 116.9 (13) |
C3—C4—C5 | 109.23 (14) | C5—N7—C8 | 126.76 (14) |
C2—C4—C5 | 109.73 (17) | C5—N7—H7N | 119.1 (15) |
C1—C4—C5 | 108.77 (17) | C8—N7—H7N | 113.7 (15) |
| | | |
C3—C4—C5—O6 | 5.3 (3) | C9—C10—C11—Cl14 | −179.03 (16) |
C2—C4—C5—O6 | 124.5 (2) | C10—C11—C12—C13 | −0.6 (3) |
C1—C4—C5—O6 | −114.8 (2) | Cl14—C11—C12—C13 | 178.91 (15) |
C3—C4—C5—N7 | −175.26 (19) | C11—C12—C13—C8 | 0.3 (3) |
C2—C4—C5—N7 | −56.1 (2) | C9—C8—C13—C12 | 0.1 (3) |
C1—C4—C5—N7 | 64.6 (2) | N7—C8—C13—C12 | 178.40 (17) |
C13—C8—C9—C10 | −0.2 (3) | O6—C5—N7—C8 | 2.2 (3) |
N7—C8—C9—C10 | −178.43 (18) | C4—C5—N7—C8 | −177.22 (17) |
C8—C9—C10—C11 | −0.1 (3) | C9—C8—N7—C5 | −33.6 (3) |
C9—C10—C11—C12 | 0.5 (3) | C13—C8—N7—C5 | 148.14 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7N···O6i | 0.84 (2) | 2.14 (2) | 2.9773 (19) | 172 (2) |
Symmetry code: (i) −x+3/2, y+1/2, z. |